##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'from SHELXL-97'
_journal_date_recd_electronic     2010-03-04
_journal_date_accepted     2010-03-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o233
_journal_page_last     o240
_journal_paper_category     FO
_journal_coeditor_code     FA3218
_publ_contact_author_name
;
Professor Christopher Glidewell
;
_publ_contact_author_address
;
University of St Andrews,
Fife KY16 9ST, UK
;
_publ_contact_author_email     'cg@st-andrews.ac.uk'
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
Five 2-aryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: isolated molecules
and hydrogen-bonded chains and sheets
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gómez, Sandra L.' .
;
Laboratorio de Síntesis Orgánica,
Escuela de Química,
Universidad Industrial de Santander,
AA 678 Bucaramanga
Colombia
;
    'Palma, Alirio' .
;
Laboratorio de Síntesis Orgánica,
Escuela de Química,
Universidad Industrial de Santander,
AA 678 Bucaramanga
Colombia
;
    'Cobo, Justo' .
;
Departamento de Química Inorgánica y Orgánica,
Universidad de Jaén
23071 Jaén
Spain
;
    'Glidewell, Christopher' .
;
School of Chemistry, University of St Andrews,
Fife KY16 9ST, Scotland
;
data_I
_chemical_name_systematic
;
2-exo-phenyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H15 N O'
_chemical_formula_sum     'C16 H15 N O'
_chemical_formula_iupac     'C16 H15 N O'
_chemical_formula_weight     237.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C c'
_symmetry_space_group_name_Hall     'C -2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     10.7475(7)
_cell_length_b     10.7842(12)
_cell_length_c     20.5812(19)
_cell_angle_alpha     90.00
_cell_angle_beta     91.688(7)
_cell_angle_gamma     90.00
_cell_volume     2384.4(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5413
_cell_measurement_theta_min     2.68
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.51
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.322
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1008
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.952
_exptl_absorpt_correction_T_max     0.985
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker-Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     15795
_diffrn_reflns_av_R_equivalents     0.0718
_diffrn_reflns_av_sigmaI/netI     0.0530
_diffrn_reflns_theta_min     2.68
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2214
_reflns_number_gt     1595
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0848
_refine_ls_R_factor_gt     0.0464
_refine_ls_wR_factor_gt     0.1022
_refine_ls_wR_factor_ref     0.1226
_refine_ls_goodness_of_fit_ref     1.080
_refine_ls_restrained_S_all     1.079
_refine_ls_number_reflns     2214
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0723P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.220
_refine_diff_density_min     -0.238
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'Sir2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N11 0.5685(3) 0.7061(3) 0.60957(17) 0.0285(9) Uani d . 1 . .
    C C12 0.6793(4) 0.7809(4) 0.6238(2) 0.0259(10) Uani d . 1 . .
    H H12 0.6899 0.7922 0.6718 0.031 Uiso calc R 1 . .
    C C13 0.7874(4) 0.6991(4) 0.5985(2) 0.0335(11) Uani d . 1 . .
    H H13A 0.8472 0.7491 0.5739 0.040 Uiso calc R 1 . .
    H H13B 0.8323 0.6565 0.6347 0.040 Uiso calc R 1 . .
    C C14 0.7179(4) 0.6062(4) 0.5541(2) 0.0314(10) Uani d . 1 . .
    H H14 0.7587 0.5990 0.5112 0.038 Uiso calc R 1 . .
    C C15 0.7013(4) 0.4814(4) 0.5842(2) 0.0347(11) Uani d . 1 . .
    H H15A 0.7831 0.4490 0.5997 0.042 Uiso calc R 1 . .
    H H15B 0.6664 0.4231 0.5513 0.042 Uiso calc R 1 . .
    C C15A 0.6150(4) 0.4901(4) 0.6404(2) 0.0313(11) Uani d . 1 . .
    C C16 0.5907(4) 0.3902(4) 0.6799(2) 0.0352(11) Uani d . 1 . .
    H H16 0.6246 0.3111 0.6704 0.042 Uiso calc R 1 . .
    C C17 0.5174(5) 0.4047(5) 0.7331(2) 0.0421(13) Uani d . 1 . .
    H H17 0.5013 0.3354 0.7601 0.051 Uiso calc R 1 . .
    C C18 0.4676(4) 0.5175(5) 0.7475(2) 0.0387(12) Uani d . 1 . .
    H H18 0.4196 0.5272 0.7852 0.046 Uiso calc R 1 . .
    C C19 0.4870(4) 0.6166(4) 0.7076(2) 0.0327(11) Uani d . 1 . .
    H H19 0.4519 0.6952 0.7171 0.039 Uiso calc R 1 . .
    C C19A 0.5581(4) 0.6011(4) 0.6534(2) 0.0268(10) Uani d . 1 . .
    O O114 0.5946(3) 0.6593(3) 0.54637(13) 0.0317(7) Uani d . 1 . .
    C C121 0.6698(4) 0.9051(4) 0.5915(2) 0.0269(10) Uani d . 1 . .
    C C122 0.7662(4) 0.9894(4) 0.5998(2) 0.0300(10) Uani d . 1 . .
    H H122 0.8386 0.9665 0.6245 0.036 Uiso calc R 1 . .
    C C123 0.7586(4) 1.1057(4) 0.5727(2) 0.0335(11) Uani d . 1 . .
    H H123 0.8245 1.1634 0.5795 0.040 Uiso calc R 1 . .
    C C124 0.6541(4) 1.1382(4) 0.5355(2) 0.0341(11) Uani d . 1 . .
    H H124 0.6489 1.2182 0.5164 0.041 Uiso calc R 1 . .
    C C125 0.5588(4) 1.0561(4) 0.5263(2) 0.0326(11) Uani d . 1 . .
    H H125 0.4878 1.0787 0.5003 0.039 Uiso calc R 1 . .
    C C126 0.5655(4) 0.9403(4) 0.5545(2) 0.0294(10) Uani d . 1 . .
    H H126 0.4981 0.8840 0.5486 0.035 Uiso calc R 1 . .
    N N21 0.7876(3) 0.4263(3) 0.36684(16) 0.0288(8) Uani d . 1 . .
    C C22 0.7110(4) 0.3170(4) 0.3524(2) 0.0274(10) Uani d . 1 . .
    H H22 0.6995 0.3077 0.3043 0.033 Uiso calc R 1 . .
    C C23 0.7899(4) 0.2085(4) 0.3796(2) 0.0305(11) Uani d . 1 . .
    H H23A 0.7380 0.1489 0.4035 0.037 Uiso calc R 1 . .
    H H23B 0.8323 0.1641 0.3444 0.037 Uiso calc R 1 . .
    C C24 0.8840(4) 0.2732(4) 0.4255(2) 0.0325(11) Uani d . 1 . .
    H H24 0.8893 0.2305 0.4686 0.039 Uiso calc R 1 . .
    C C25 1.0120(4) 0.2883(4) 0.3977(2) 0.0323(10) Uani d . 1 . .
    H H25A 1.0699 0.3238 0.4311 0.039 Uiso calc R 1 . .
    H H25B 1.0445 0.2064 0.3846 0.039 Uiso calc R 1 . .
    C C25A 1.0035(4) 0.3721(4) 0.3402(2) 0.0280(10) Uani d . 1 . .
    C C26 1.1023(4) 0.3900(4) 0.2996(2) 0.0360(11) Uani d . 1 . .
    H H26 1.1805 0.3534 0.3106 0.043 Uiso calc R 1 . .
    C C27 1.0898(5) 0.4597(4) 0.2439(2) 0.0365(12) Uani d . 1 . .
    H H27 1.1587 0.4706 0.2166 0.044 Uiso calc R 1 . .
    C C28 0.9769(4) 0.5135(5) 0.2278(2) 0.0353(12) Uani d . 1 . .
    H H28 0.9670 0.5591 0.1885 0.042 Uiso calc R 1 . .
    C C29 0.8782(4) 0.5017(4) 0.2684(2) 0.0322(11) Uani d . 1 . .
    H H29 0.8009 0.5404 0.2578 0.039 Uiso calc R 1 . .
    C C29A 0.8925(4) 0.4332(4) 0.3247(2) 0.0277(10) Uani d . 1 . .
    O O214 0.8349(3) 0.3967(3) 0.43189(14) 0.0312(7) Uani d . 1 . .
    C C221 0.5851(4) 0.3272(4) 0.3831(2) 0.0284(10) Uani d . 1 . .
    C C222 0.4991(4) 0.2345(4) 0.3722(2) 0.0298(10) Uani d . 1 . .
    H H222 0.5197 0.1654 0.3460 0.036 Uiso calc R 1 . .
    C C223 0.3836(4) 0.2410(4) 0.3990(2) 0.0324(11) Uani d . 1 . .
    H H223 0.3244 0.1771 0.3907 0.039 Uiso calc R 1 . .
    C C224 0.3535(4) 0.3398(4) 0.4378(2) 0.0340(11) Uani d . 1 . .
    H H224 0.2740 0.3439 0.4567 0.041 Uiso calc R 1 . .
    C C225 0.4393(4) 0.4324(4) 0.4491(2) 0.0321(11) Uani d . 1 . .
    H H225 0.4196 0.5004 0.4763 0.039 Uiso calc R 1 . .
    C C226 0.5541(4) 0.4266(4) 0.4208(2) 0.0294(10) Uani d . 1 . .
    H H226 0.6121 0.4921 0.4276 0.035 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N11 O114 . 1.430(4) ?
    N11 C19A . 1.455(5) ?
    N11 C12 . 1.460(5) ?
    C12 C121 . 1.497(6) ?
    C12 C13 . 1.560(6) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.535(6) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 O114 . 1.448(5) ?
    C14 C15 . 1.495(6) ?
    C14 H14 . 1.0000 ?
    C15 C15A . 1.506(7) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15A C19A . 1.375(6) ?
    C15A C16 . 1.379(6) ?
    C16 C17 . 1.376(7) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.366(7) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.367(6) ?
    C18 H18 . 0.9500 ?
    C19 C19A . 1.380(6) ?
    C19 H19 . 0.9500 ?
    C121 C122 . 1.385(6) ?
    C121 C126 . 1.389(6) ?
    C122 C123 . 1.373(6) ?
    C122 H122 . 0.9500 ?
    C123 C124 . 1.385(7) ?
    C123 H123 . 0.9500 ?
    C124 C125 . 1.363(7) ?
    C124 H124 . 0.9500 ?
    C125 C126 . 1.379(6) ?
    C125 H125 . 0.9500 ?
    C126 H126 . 0.9500 ?
    N21 C29A . 1.444(5) ?
    N21 O214 . 1.453(5) ?
    N21 C22 . 1.463(5) ?
    C22 C221 . 1.515(6) ?
    C22 C23 . 1.541(6) ?
    C22 H22 . 1.0000 ?
    C23 C24 . 1.531(6) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 O214 . 1.440(5) ?
    C24 C25 . 1.514(6) ?
    C24 H24 . 1.0000 ?
    C25 C25A . 1.490(6) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C25A C26 . 1.382(6) ?
    C25A C29A . 1.392(6) ?
    C26 C27 . 1.376(7) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.377(7) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.375(6) ?
    C28 H28 . 0.9500 ?
    C29 C29A . 1.378(6) ?
    C29 H29 . 0.9500 ?
    C221 C226 . 1.370(6) ?
    C221 C222 . 1.375(6) ?
    C222 C223 . 1.375(6) ?
    C222 H222 . 0.9500 ?
    C223 C224 . 1.376(7) ?
    C223 H223 . 0.9500 ?
    C224 C225 . 1.374(6) ?
    C224 H224 . 0.9500 ?
    C225 C226 . 1.381(6) ?
    C225 H225 . 0.9500 ?
    C226 H226 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O114 N11 C19A . . 108.1(3) ?
    O114 N11 C12 . . 101.3(3) ?
    C19A N11 C12 . . 112.5(3) ?
    N11 C12 C121 . . 111.2(3) ?
    N11 C12 C13 . . 103.4(3) ?
    C121 C12 C13 . . 113.6(3) ?
    N11 C12 H12 . . 109.5 ?
    C121 C12 H12 . . 109.5 ?
    C13 C12 H12 . . 109.5 ?
    C14 C13 C12 . . 102.3(3) ?
    C14 C13 H13A . . 111.3 ?
    C12 C13 H13A . . 111.3 ?
    C14 C13 H13B . . 111.3 ?
    C12 C13 H13B . . 111.3 ?
    H13A C13 H13B . . 109.2 ?
    O114 C14 C15 . . 106.4(3) ?
    O114 C14 C13 . . 103.6(3) ?
    C15 C14 C13 . . 113.8(4) ?
    O114 C14 H14 . . 110.9 ?
    C15 C14 H14 . . 110.9 ?
    C13 C14 H14 . . 110.9 ?
    C14 C15 C15A . . 110.2(4) ?
    C14 C15 H15A . . 109.6 ?
    C15A C15 H15A . . 109.6 ?
    C14 C15 H15B . . 109.6 ?
    C15A C15 H15B . . 109.6 ?
    H15A C15 H15B . . 108.1 ?
    C19A C15A C16 . . 118.2(4) ?
    C19A C15A C15 . . 119.4(4) ?
    C16 C15A C15 . . 122.4(4) ?
    C17 C16 C15A . . 120.2(5) ?
    C17 C16 H16 . . 119.9 ?
    C15A C16 H16 . . 119.9 ?
    C18 C17 C16 . . 120.8(4) ?
    C18 C17 H17 . . 119.6 ?
    C16 C17 H17 . . 119.6 ?
    C17 C18 C19 . . 119.9(5) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C18 C19 C19A . . 119.2(4) ?
    C18 C19 H19 . . 120.4 ?
    C19A C19 H19 . . 120.4 ?
    C15A C19A C19 . . 121.5(4) ?
    C15A C19A N11 . . 120.9(4) ?
    C19 C19A N11 . . 117.5(4) ?
    N11 O114 C14 . . 104.0(3) ?
    C122 C121 C126 . . 118.4(4) ?
    C122 C121 C12 . . 119.5(4) ?
    C126 C121 C12 . . 122.1(4) ?
    C123 C122 C121 . . 121.0(4) ?
    C123 C122 H122 . . 119.5 ?
    C121 C122 H122 . . 119.5 ?
    C122 C123 C124 . . 119.5(4) ?
    C122 C123 H123 . . 120.3 ?
    C124 C123 H123 . . 120.3 ?
    C125 C124 C123 . . 120.4(4) ?
    C125 C124 H124 . . 119.8 ?
    C123 C124 H124 . . 119.8 ?
    C124 C125 C126 . . 120.0(4) ?
    C124 C125 H125 . . 120.0 ?
    C126 C125 H125 . . 120.0 ?
    C125 C126 C121 . . 120.7(4) ?
    C125 C126 H126 . . 119.7 ?
    C121 C126 H126 . . 119.7 ?
    C29A N21 O214 . . 107.9(3) ?
    C29A N21 C22 . . 111.4(3) ?
    O214 N21 C22 . . 100.9(3) ?
    N21 C22 C221 . . 111.2(3) ?
    N21 C22 C23 . . 103.8(3) ?
    C221 C22 C23 . . 113.1(3) ?
    N21 C22 H22 . . 109.5 ?
    C221 C22 H22 . . 109.5 ?
    C23 C22 H22 . . 109.5 ?
    C24 C23 C22 . . 102.9(3) ?
    C24 C23 H23A . . 111.2 ?
    C22 C23 H23A . . 111.2 ?
    C24 C23 H23B . . 111.2 ?
    C22 C23 H23B . . 111.2 ?
    H23A C23 H23B . . 109.1 ?
    O214 C24 C25 . . 105.9(4) ?
    O214 C24 C23 . . 104.0(3) ?
    C25 C24 C23 . . 114.0(4) ?
    O214 C24 H24 . . 110.9 ?
    C25 C24 H24 . . 110.8 ?
    C23 C24 H24 . . 110.9 ?
    C25A C25 C24 . . 109.3(4) ?
    C25A C25 H25A . . 109.8 ?
    C24 C25 H25A . . 109.8 ?
    C25A C25 H25B . . 109.8 ?
    C24 C25 H25B . . 109.8 ?
    H25A C25 H25B . . 108.3 ?
    C26 C25A C29A . . 117.6(4) ?
    C26 C25A C25 . . 122.3(4) ?
    C29A C25A C25 . . 120.1(4) ?
    C27 C26 C25A . . 121.5(5) ?
    C27 C26 H26 . . 119.2 ?
    C25A C26 H26 . . 119.2 ?
    C26 C27 C28 . . 119.6(4) ?
    C26 C27 H27 . . 120.2 ?
    C28 C27 H27 . . 120.2 ?
    C29 C28 C27 . . 120.3(4) ?
    C29 C28 H28 . . 119.8 ?
    C27 C28 H28 . . 119.8 ?
    C28 C29 C29A . . 119.5(4) ?
    C28 C29 H29 . . 120.3 ?
    C29A C29 H29 . . 120.3 ?
    C29 C29A C25A . . 121.3(4) ?
    C29 C29A N21 . . 117.6(4) ?
    C25A C29A N21 . . 121.1(4) ?
    C24 O214 N21 . . 103.7(3) ?
    C226 C221 C222 . . 119.2(4) ?
    C226 C221 C22 . . 121.9(4) ?
    C222 C221 C22 . . 118.9(4) ?
    C221 C222 C223 . . 120.5(4) ?
    C221 C222 H222 . . 119.7 ?
    C223 C222 H222 . . 119.7 ?
    C224 C223 C222 . . 120.2(4) ?
    C224 C223 H223 . . 119.9 ?
    C222 C223 H223 . . 119.9 ?
    C225 C224 C223 . . 119.5(4) ?
    C225 C224 H224 . . 120.3 ?
    C223 C224 H224 . . 120.3 ?
    C224 C225 C226 . . 120.0(4) ?
    C224 C225 H225 . . 120.0 ?
    C226 C225 H225 . . 120.0 ?
    C221 C226 C225 . . 120.6(4) ?
    C221 C226 H226 . . 119.7 ?
    C225 C226 H226 . . 119.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O114 N11 C12 C121 . . . . 80.8(4) ?
    C19A N11 C12 C121 . . . . -163.9(3) ?
    O114 N11 C12 C13 . . . . -41.4(4) ?
    C19A N11 C12 C13 . . . . 73.8(4) ?
    N11 C12 C13 C14 . . . . 17.1(4) ?
    C121 C12 C13 C14 . . . . -103.5(4) ?
    C12 C13 C14 O114 . . . . 13.0(4) ?
    C12 C13 C14 C15 . . . . -102.0(4) ?
    O114 C14 C15 C15A . . . . -46.5(5) ?
    C13 C14 C15 C15A . . . . 66.9(5) ?
    C14 C15 C15A C19A . . . . 4.7(5) ?
    C14 C15 C15A C16 . . . . -175.2(4) ?
    C19A C15A C16 C17 . . . . -4.0(7) ?
    C15 C15A C16 C17 . . . . 175.9(4) ?
    C15A C16 C17 C18 . . . . 0.1(7) ?
    C16 C17 C18 C19 . . . . 2.2(7) ?
    C17 C18 C19 C19A . . . . -0.7(7) ?
    C16 C15A C19A C19 . . . . 5.6(6) ?
    C15 C15A C19A C19 . . . . -174.3(4) ?
    C16 C15A C19A N11 . . . . -173.0(4) ?
    C15 C15A C19A N11 . . . . 7.1(6) ?
    C18 C19 C19A C15A . . . . -3.3(6) ?
    C18 C19 C19A N11 . . . . 175.4(4) ?
    O114 N11 C19A C15A . . . . 24.1(5) ?
    C12 N11 C19A C15A . . . . -87.0(5) ?
    O114 N11 C19A C19 . . . . -154.6(3) ?
    C12 N11 C19A C19 . . . . 94.3(4) ?
    C19A N11 O114 C14 . . . . -66.7(3) ?
    C12 N11 O114 C14 . . . . 51.8(3) ?
    C15 C14 O114 N11 . . . . 80.3(4) ?
    C13 C14 O114 N11 . . . . -39.9(4) ?
    N11 C12 C121 C122 . . . . 179.6(4) ?
    C13 C12 C121 C122 . . . . -64.3(5) ?
    N11 C12 C121 C126 . . . . 1.2(5) ?
    C13 C12 C121 C126 . . . . 117.3(4) ?
    C126 C121 C122 C123 . . . . 0.8(6) ?
    C12 C121 C122 C123 . . . . -177.8(4) ?
    C121 C122 C123 C124 . . . . -1.3(6) ?
    C122 C123 C124 C125 . . . . 0.6(7) ?
    C123 C124 C125 C126 . . . . 0.7(7) ?
    C124 C125 C126 C121 . . . . -1.3(6) ?
    C122 C121 C126 C125 . . . . 0.6(6) ?
    C12 C121 C126 C125 . . . . 179.0(4) ?
    C29A N21 C22 C221 . . . . -164.8(3) ?
    O214 N21 C22 C221 . . . . 80.9(4) ?
    C29A N21 C22 C23 . . . . 73.3(4) ?
    O214 N21 C22 C23 . . . . -41.0(4) ?
    N21 C22 C23 C24 . . . . 17.4(4) ?
    C221 C22 C23 C24 . . . . -103.2(4) ?
    C22 C23 C24 O214 . . . . 12.8(4) ?
    C22 C23 C24 C25 . . . . -102.1(4) ?
    O214 C24 C25 C25A . . . . -49.2(5) ?
    C23 C24 C25 C25A . . . . 64.5(5) ?
    C24 C25 C25A C26 . . . . -171.2(4) ?
    C24 C25 C25A C29A . . . . 7.1(6) ?
    C29A C25A C26 C27 . . . . -3.7(6) ?
    C25 C25A C26 C27 . . . . 174.6(4) ?
    C25A C26 C27 C28 . . . . 0.3(7) ?
    C26 C27 C28 C29 . . . . 2.4(7) ?
    C27 C28 C29 C29A . . . . -1.4(6) ?
    C28 C29 C29A C25A . . . . -2.2(6) ?
    C28 C29 C29A N21 . . . . 178.2(4) ?
    C26 C25A C29A C29 . . . . 4.7(6) ?
    C25 C25A C29A C29 . . . . -173.7(4) ?
    C26 C25A C29A N21 . . . . -175.7(4) ?
    C25 C25A C29A N21 . . . . 5.9(6) ?
    O214 N21 C29A C29 . . . . -157.0(3) ?
    C22 N21 C29A C29 . . . . 93.1(4) ?
    O214 N21 C29A C25A . . . . 23.4(5) ?
    C22 N21 C29A C25A . . . . -86.5(5) ?
    C25 C24 O214 N21 . . . . 81.4(4) ?
    C23 C24 O214 N21 . . . . -39.1(4) ?
    C29A N21 O214 C24 . . . . -66.1(4) ?
    C22 N21 O214 C24 . . . . 50.8(3) ?
    N21 C22 C221 C226 . . . . -2.0(6) ?
    C23 C22 C221 C226 . . . . 114.3(5) ?
    N21 C22 C221 C222 . . . . 177.4(4) ?
    C23 C22 C221 C222 . . . . -66.3(5) ?
    C226 C221 C222 C223 . . . . -0.3(6) ?
    C22 C221 C222 C223 . . . . -179.6(4) ?
    C221 C222 C223 C224 . . . . -0.9(7) ?
    C222 C223 C224 C225 . . . . 0.7(7) ?
    C223 C224 C225 C226 . . . . 0.8(7) ?
    C222 C221 C226 C225 . . . . 1.7(6) ?
    C22 C221 C226 C225 . . . . -178.9(4) ?
    C224 C225 C226 C221 . . . . -2.0(6) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C122 H122 Cg1 3_555 0.95 2.58 3.469(5) 156 no
    C222 H222 Cg2 3_445 0.95 2.71 3.610(5) 158 no
data_II
_chemical_name_systematic
;
2-exo-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H- 1,4-epoxy-1-benzazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 Cl N O'
_chemical_formula_sum     'C16 H14 Cl N O'
_chemical_formula_iupac     'C16 H14 Cl N O'
_chemical_formula_weight     271.73
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.2405(14)
_cell_length_b     11.5432(16)
_cell_length_c     27.442(2)
_cell_angle_alpha     90.00
_cell_angle_beta     101.030(13)
_cell_angle_gamma     90.00
_cell_volume     2562.1(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5872
_cell_measurement_theta_min     2.87
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.46
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.409
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1136
_exptl_absorpt_coefficient_mu     0.288
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.889
_exptl_absorpt_correction_T_max     0.972
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker-Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     33797
_diffrn_reflns_av_R_equivalents     0.0789
_diffrn_reflns_av_sigmaI/netI     0.0628
_diffrn_reflns_theta_min     2.87
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4745
_reflns_number_gt     2978
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1036
_refine_ls_R_factor_gt     0.0501
_refine_ls_wR_factor_gt     0.0903
_refine_ls_wR_factor_ref     0.1077
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     4745
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0357P)²+1.7145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.249
_refine_diff_density_min     -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'Sir2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N11 0.2494(3) 0.70287(18) 0.59772(8) 0.0216(5) Uani d . 1 . .
    C C12 0.3759(3) 0.6277(2) 0.57911(9) 0.0236(7) Uani d . 1 . .
    H H12 0.4878 0.6634 0.5894 0.028 Uiso calc R 1 . .
    C C13 0.3675(3) 0.5162(2) 0.60967(10) 0.0257(7) Uani d . 1 . .
    H H13A 0.4639 0.5111 0.6373 0.031 Uiso calc R 1 . .
    H H13B 0.3660 0.4467 0.5884 0.031 Uiso calc R 1 . .
    C C14 0.2029(3) 0.5258(2) 0.63003(10) 0.0262(7) Uani d . 1 . .
    H H14 0.1366 0.4530 0.6229 0.031 Uiso calc R 1 . .
    C C15 0.2153(4) 0.5608(2) 0.68353(10) 0.0306(7) Uani d . 1 . .
    H H15A 0.1045 0.5609 0.6925 0.037 Uiso calc R 1 . .
    H H15B 0.2871 0.5062 0.7057 0.037 Uiso calc R 1 . .
    C C15A 0.2875(3) 0.6796(2) 0.68854(10) 0.0265(7) Uani d . 1 . .
    C C16 0.3425(4) 0.7268(3) 0.73445(11) 0.0357(8) Uani d . 1 . .
    H H16 0.3320 0.6851 0.7635 0.043 Uiso calc R 1 . .
    C C17 0.4126(4) 0.8342(3) 0.73820(11) 0.0401(9) Uani d . 1 . .
    H H17 0.4509 0.8666 0.7702 0.048 Uiso calc R 1 . .
    C C18 0.4295(3) 0.8975(3) 0.69640(12) 0.0375(8) Uani d . 1 . .
    H H18 0.4794 0.9720 0.7000 0.045 Uiso calc R 1 . .
    C C19 0.3747(3) 0.8531(2) 0.65036(11) 0.0275(7) Uani d . 1 . .
    H H19 0.3855 0.8954 0.6214 0.033 Uiso calc R 1 . .
    C C19A 0.3035(3) 0.7454(2) 0.64698(10) 0.0213(6) Uani d . 1 . .
    O O114 0.1214(2) 0.61920(15) 0.60195(7) 0.0248(5) Uani d . 1 . .
    C C121 0.3386(3) 0.6157(2) 0.52387(10) 0.0232(6) Uani d . 1 . .
    C C122 0.3940(3) 0.7003(3) 0.49413(10) 0.0287(7) Uani d . 1 . .
    H H122 0.4610 0.7614 0.5101 0.034 Uiso calc R 1 . .
    C C123 0.3564(3) 0.6991(3) 0.44350(10) 0.0292(7) Uani d . 1 . .
    H H123 0.3957 0.7572 0.4241 0.035 Uiso calc R 1 . .
    C C124 0.2604(3) 0.6112(2) 0.42243(9) 0.0242(7) Uani d . 1 . .
    Cl Cl14 0.20919(9) 0.61232(7) 0.35845(3) 0.0335(2) Uani d . 1 . .
    C C125 0.2041(3) 0.5247(2) 0.45053(10) 0.0284(7) Uani d . 1 . .
    H H125 0.1381 0.4633 0.4344 0.034 Uiso calc R 1 . .
    C C126 0.2436(3) 0.5281(2) 0.50131(10) 0.0266(7) Uani d . 1 . .
    H H126 0.2047 0.4695 0.5205 0.032 Uiso calc R 1 . .
    N N21 0.2571(3) 0.14072(18) 0.39458(8) 0.0220(5) Uani d . 1 . .
    C C22 0.1153(3) 0.1435(2) 0.42322(9) 0.0215(6) Uani d . 1 . .
    H H22 0.0402 0.2093 0.4105 0.026 Uiso calc R 1 . .
    C C23 0.0233(3) 0.0300(2) 0.40910(10) 0.0270(7) Uani d . 1 . .
    H H23A -0.0875 0.0442 0.3886 0.032 Uiso calc R 1 . .
    H H23B 0.0110 -0.0147 0.4390 0.032 Uiso calc R 1 . .
    C C24 0.1377(4) -0.0348(3) 0.37870(11) 0.0329(7) Uani d . 1 . .
    H H24 0.1445 -0.1190 0.3875 0.039 Uiso calc R 1 . .
    C C25 0.0993(4) -0.0196(3) 0.32351(11) 0.0405(8) Uani d . 1 . .
    H H25A -0.0189 -0.0371 0.3110 0.049 Uiso calc R 1 . .
    H H25B 0.1660 -0.0749 0.3080 0.049 Uiso calc R 1 . .
    C C25A 0.1359(3) 0.1021(3) 0.30895(10) 0.0295(7) Uani d . 1 . .
    C C26 0.0981(4) 0.1426(3) 0.26116(11) 0.0374(8) Uani d . 1 . .
    H H26 0.0505 0.0909 0.2354 0.045 Uiso calc R 1 . .
    C C27 0.1268(4) 0.2555(3) 0.24918(11) 0.0376(8) Uani d . 1 . .
    H H27 0.0992 0.2804 0.2156 0.045 Uiso calc R 1 . .
    C C28 0.1938(3) 0.3309(3) 0.28487(10) 0.0327(7) Uani d . 1 . .
    H H28 0.2117 0.4095 0.2771 0.039 Uiso calc R 1 . .
    C C29 0.2353(3) 0.2915(2) 0.33250(10) 0.0260(7) Uani d . 1 . .
    H H29 0.2839 0.3432 0.3581 0.031 Uiso calc R 1 . .
    C C29A 0.2079(3) 0.1780(2) 0.34421(9) 0.0223(7) Uani d . 1 . .
    O O214 0.2948(2) 0.01854(16) 0.39317(7) 0.0305(5) Uani d . 1 . .
    C C221 0.1646(3) 0.1548(2) 0.47796(9) 0.0204(6) Uani d . 1 . .
    C C222 0.0808(3) 0.2300(2) 0.50528(10) 0.0233(6) Uani d . 1 . .
    H H222 -0.0092 0.2740 0.4878 0.028 Uiso calc R 1 . .
    C C223 0.1227(3) 0.2425(2) 0.55562(10) 0.0256(7) Uani d . 1 . .
    H H223 0.0637 0.2929 0.5734 0.031 Uiso calc R 1 . .
    C C224 0.2515(3) 0.1799(2) 0.57845(9) 0.0243(7) Uani d . 1 . .
    Cl Cl24 0.30581(10) 0.19796(7) 0.64167(3) 0.0369(2) Uani d . 1 . .
    C C225 0.3350(3) 0.1026(2) 0.55234(10) 0.0260(7) Uani d . 1 . .
    H H225 0.4244 0.0583 0.5700 0.031 Uiso calc R 1 . .
    C C226 0.2910(3) 0.0899(2) 0.50248(10) 0.0235(7) Uani d . 1 . .
    H H226 0.3475 0.0368 0.4852 0.028 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N11 C19A . 1.427(3) ?
    N11 O114 . 1.451(3) ?
    N11 C12 . 1.518(3) ?
    C12 C121 . 1.494(4) ?
    C12 C13 . 1.545(4) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.567(4) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 O114 . 1.418(3) ?
    C14 C15 . 1.508(4) ?
    C14 H14 . 1.0000 ?
    C15 C15A . 1.490(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15A C16 . 1.368(4) ?
    C15A C19A . 1.398(4) ?
    C16 C17 . 1.363(4) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.389(4) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.358(4) ?
    C18 H18 . 0.9500 ?
    C19 C19A . 1.370(4) ?
    C19 H19 . 0.9500 ?
    C121 C126 . 1.354(4) ?
    C121 C122 . 1.404(4) ?
    C122 C123 . 1.365(4) ?
    C122 H122 . 0.9500 ?
    C123 C124 . 1.347(4) ?
    C123 H123 . 0.9500 ?
    C124 C125 . 1.394(4) ?
    C124 Cl14 . 1.726(3) ?
    C125 C126 . 1.370(4) ?
    C125 H125 . 0.9500 ?
    C126 H126 . 0.9500 ?
    N21 C29A . 1.430(3) ?
    N21 O214 . 1.446(3) ?
    N21 C22 . 1.528(3) ?
    C22 C221 . 1.485(3) ?
    C22 C23 . 1.527(4) ?
    C22 H22 . 1.0000 ?
    C23 C24 . 1.563(4) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 O214 . 1.420(3) ?
    C24 C25 . 1.497(4) ?
    C24 H24 . 1.0000 ?
    C25 C25A . 1.506(4) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C25A C29A . 1.355(4) ?
    C25A C26 . 1.371(4) ?
    C26 C27 . 1.375(4) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.347(4) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.364(4) ?
    C28 H28 . 0.9500 ?
    C29 C29A . 1.378(4) ?
    C29 H29 . 0.9500 ?
    C221 C226 . 1.353(3) ?
    C221 C222 . 1.411(4) ?
    C222 C223 . 1.366(4) ?
    C222 H222 . 0.9500 ?
    C223 C224 . 1.337(4) ?
    C223 H223 . 0.9500 ?
    C224 C225 . 1.404(4) ?
    C224 Cl24 . 1.719(3) ?
    C225 C226 . 1.355(4) ?
    C225 H225 . 0.9500 ?
    C226 H226 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C19A N11 O114 . . 104.68(19) ?
    C19A N11 C12 . . 113.91(19) ?
    O114 N11 C12 . . 101.70(18) ?
    C121 C12 N11 . . 111.9(2) ?
    C121 C12 C13 . . 116.8(2) ?
    N11 C12 C13 . . 100.9(2) ?
    C121 C12 H12 . . 108.9 ?
    N11 C12 H12 . . 108.9 ?
    C13 C12 H12 . . 108.9 ?
    C12 C13 C14 . . 105.4(2) ?
    C12 C13 H13A . . 110.7 ?
    C14 C13 H13A . . 110.7 ?
    C12 C13 H13B . . 110.7 ?
    C14 C13 H13B . . 110.7 ?
    H13A C13 H13B . . 108.8 ?
    O114 C14 C15 . . 105.2(2) ?
    O114 C14 C13 . . 102.3(2) ?
    C15 C14 C13 . . 117.7(2) ?
    O114 C14 H14 . . 110.4 ?
    C15 C14 H14 . . 110.4 ?
    C13 C14 H14 . . 110.4 ?
    C15A C15 C14 . . 106.8(2) ?
    C15A C15 H15A . . 110.4 ?
    C14 C15 H15A . . 110.4 ?
    C15A C15 H15B . . 110.4 ?
    C14 C15 H15B . . 110.4 ?
    H15A C15 H15B . . 108.6 ?
    C16 C15A C19A . . 117.9(3) ?
    C16 C15A C15 . . 120.5(3) ?
    C19A C15A C15 . . 121.6(2) ?
    C17 C16 C15A . . 119.6(3) ?
    C17 C16 H16 . . 120.2 ?
    C15A C16 H16 . . 120.2 ?
    C16 C17 C18 . . 121.6(3) ?
    C16 C17 H17 . . 119.2 ?
    C18 C17 H17 . . 119.2 ?
    C19 C18 C17 . . 120.2(3) ?
    C19 C18 H18 . . 119.9 ?
    C17 C18 H18 . . 119.9 ?
    C18 C19 C19A . . 117.8(3) ?
    C18 C19 H19 . . 121.1 ?
    C19A C19 H19 . . 121.1 ?
    C19 C19A C15A . . 123.0(3) ?
    C19 C19A N11 . . 115.4(2) ?
    C15A C19A N11 . . 121.6(2) ?
    C14 O114 N11 . . 105.90(18) ?
    C126 C121 C122 . . 118.5(2) ?
    C126 C121 C12 . . 121.5(3) ?
    C122 C121 C12 . . 119.9(2) ?
    C123 C122 C121 . . 123.3(3) ?
    C123 C122 H122 . . 118.3 ?
    C121 C122 H122 . . 118.3 ?
    C124 C123 C122 . . 116.4(3) ?
    C124 C123 H123 . . 121.8 ?
    C122 C123 H123 . . 121.8 ?
    C123 C124 C125 . . 122.2(2) ?
    C123 C124 Cl14 . . 116.1(2) ?
    C125 C124 Cl14 . . 121.7(2) ?
    C126 C125 C124 . . 120.2(3) ?
    C126 C125 H125 . . 119.9 ?
    C124 C125 H125 . . 119.9 ?
    C121 C126 C125 . . 119.4(3) ?
    C121 C126 H126 . . 120.3 ?
    C125 C126 H126 . . 120.3 ?
    C29A N21 O214 . . 106.86(19) ?
    C29A N21 C22 . . 112.81(19) ?
    O214 N21 C22 . . 102.92(18) ?
    C221 C22 C23 . . 111.0(2) ?
    C221 C22 N21 . . 115.7(2) ?
    C23 C22 N21 . . 104.0(2) ?
    C221 C22 H22 . . 108.6 ?
    C23 C22 H22 . . 108.6 ?
    N21 C22 H22 . . 108.6 ?
    C22 C23 C24 . . 103.0(2) ?
    C22 C23 H23A . . 111.2 ?
    C24 C23 H23A . . 111.2 ?
    C22 C23 H23B . . 111.2 ?
    C24 C23 H23B . . 111.2 ?
    H23A C23 H23B . . 109.1 ?
    O214 C24 C25 . . 103.7(2) ?
    O214 C24 C23 . . 104.7(2) ?
    C25 C24 C23 . . 116.8(3) ?
    O214 C24 H24 . . 110.4 ?
    C25 C24 H24 . . 110.4 ?
    C23 C24 H24 . . 110.4 ?
    C24 C25 C25A . . 111.3(2) ?
    C24 C25 H25A . . 109.4 ?
    C25A C25 H25A . . 109.4 ?
    C24 C25 H25B . . 109.4 ?
    C25A C25 H25B . . 109.4 ?
    H25A C25 H25B . . 108.0 ?
    C29A C25A C26 . . 116.8(3) ?
    C29A C25A C25 . . 119.7(3) ?
    C26 C25A C25 . . 123.5(3) ?
    C25A C26 C27 . . 122.3(3) ?
    C25A C26 H26 . . 118.9 ?
    C27 C26 H26 . . 118.9 ?
    C28 C27 C26 . . 120.2(3) ?
    C28 C27 H27 . . 119.9 ?
    C26 C27 H27 . . 119.9 ?
    C27 C28 C29 . . 118.3(3) ?
    C27 C28 H28 . . 120.9 ?
    C29 C28 H28 . . 120.9 ?
    C28 C29 C29A . . 121.2(3) ?
    C28 C29 H29 . . 119.4 ?
    C29A C29 H29 . . 119.4 ?
    C25A C29A C29 . . 121.1(3) ?
    C25A C29A N21 . . 120.0(3) ?
    C29 C29A N21 . . 118.9(2) ?
    C24 O214 N21 . . 103.96(18) ?
    C226 C221 C222 . . 119.0(2) ?
    C226 C221 C22 . . 119.4(2) ?
    C222 C221 C22 . . 121.6(2) ?
    C223 C222 C221 . . 123.2(3) ?
    C223 C222 H222 . . 118.4 ?
    C221 C222 H222 . . 118.4 ?
    C224 C223 C222 . . 116.2(3) ?
    C224 C223 H223 . . 121.9 ?
    C222 C223 H223 . . 121.9 ?
    C223 C224 C225 . . 121.8(2) ?
    C223 C224 Cl24 . . 115.9(2) ?
    C225 C224 Cl24 . . 122.2(2) ?
    C226 C225 C224 . . 121.4(3) ?
    C226 C225 H225 . . 119.3 ?
    C224 C225 H225 . . 119.3 ?
    C221 C226 C225 . . 118.3(3) ?
    C221 C226 H226 . . 120.8 ?
    C225 C226 H226 . . 120.8 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C19A N11 C12 C121 . . . . -162.3(2) ?
    O114 N11 C12 C121 . . . . 85.7(2) ?
    C19A N11 C12 C13 . . . . 72.8(2) ?
    O114 N11 C12 C13 . . . . -39.2(2) ?
    C121 C12 C13 C14 . . . . -105.1(3) ?
    N11 C12 C13 C14 . . . . 16.4(2) ?
    C12 C13 C14 O114 . . . . 12.5(3) ?
    C12 C13 C14 C15 . . . . -102.1(3) ?
    O114 C14 C15 C15A . . . . -50.7(3) ?
    C13 C14 C15 C15A . . . . 62.3(3) ?
    C14 C15 C15A C16 . . . . -167.8(2) ?
    C14 C15 C15A C19A . . . . 11.3(3) ?
    C19A C15A C16 C17 . . . . -1.1(4) ?
    C15 C15A C16 C17 . . . . 178.1(3) ?
    C15A C16 C17 C18 . . . . 0.2(4) ?
    C16 C17 C18 C19 . . . . 0.4(5) ?
    C17 C18 C19 C19A . . . . 0.0(4) ?
    C18 C19 C19A C15A . . . . -1.0(4) ?
    C18 C19 C19A N11 . . . . -179.6(2) ?
    C16 C15A C19A C19 . . . . 1.5(4) ?
    C15 C15A C19A C19 . . . . -177.6(3) ?
    C16 C15A C19A N11 . . . . 180.0(2) ?
    C15 C15A C19A N11 . . . . 0.9(4) ?
    O114 N11 C19A C19 . . . . -156.0(2) ?
    C12 N11 C19A C19 . . . . 93.8(3) ?
    O114 N11 C19A C15A . . . . 25.5(3) ?
    C12 N11 C19A C15A . . . . -84.8(3) ?
    C15 C14 O114 N11 . . . . 84.6(2) ?
    C13 C14 O114 N11 . . . . -38.9(2) ?
    C19A N11 O114 C14 . . . . -67.8(2) ?
    C12 N11 O114 C14 . . . . 51.1(2) ?
    N11 C12 C121 C126 . . . . -90.9(3) ?
    C13 C12 C121 C126 . . . . 24.7(4) ?
    N11 C12 C121 C122 . . . . 85.2(3) ?
    C13 C12 C121 C122 . . . . -159.3(2) ?
    C126 C121 C122 C123 . . . . 0.3(4) ?
    C12 C121 C122 C123 . . . . -175.9(3) ?
    C121 C122 C123 C124 . . . . 0.3(4) ?
    C122 C123 C124 C125 . . . . -1.0(4) ?
    C122 C123 C124 Cl14 . . . . 178.5(2) ?
    C123 C124 C125 C126 . . . . 1.1(4) ?
    Cl14 C124 C125 C126 . . . . -178.3(2) ?
    C122 C121 C126 C125 . . . . -0.2(4) ?
    C12 C121 C126 C125 . . . . 175.9(3) ?
    C124 C125 C126 C121 . . . . -0.4(4) ?
    C29A N21 C22 C221 . . . . -155.4(2) ?
    O214 N21 C22 C221 . . . . 89.8(2) ?
    C29A N21 C22 C23 . . . . 82.5(2) ?
    O214 N21 C22 C23 . . . . -32.3(2) ?
    C221 C22 C23 C24 . . . . -117.8(2) ?
    N21 C22 C23 C24 . . . . 7.3(2) ?
    C22 C23 C24 O214 . . . . 20.5(3) ?
    C22 C23 C24 C25 . . . . -93.5(3) ?
    O214 C24 C25 C25A . . . . -45.5(3) ?
    C23 C24 C25 C25A . . . . 69.1(3) ?
    C24 C25 C25A C29A . . . . 5.2(4) ?
    C24 C25 C25A C26 . . . . -173.9(3) ?
    C29A C25A C26 C27 . . . . -1.9(4) ?
    C25 C25A C26 C27 . . . . 177.3(3) ?
    C25A C26 C27 C28 . . . . -0.1(5) ?
    C26 C27 C28 C29 . . . . 1.4(5) ?
    C27 C28 C29 C29A . . . . -0.7(4) ?
    C26 C25A C29A C29 . . . . 2.5(4) ?
    C25 C25A C29A C29 . . . . -176.6(3) ?
    C26 C25A C29A N21 . . . . -177.4(2) ?
    C25 C25A C29A N21 . . . . 3.4(4) ?
    C28 C29 C29A C25A . . . . -1.3(4) ?
    C28 C29 C29A N21 . . . . 178.7(2) ?
    O214 N21 C29A C25A . . . . 28.6(3) ?
    C22 N21 C29A C25A . . . . -83.8(3) ?
    O214 N21 C29A C29 . . . . -151.4(2) ?
    C22 N21 C29A C29 . . . . 96.2(3) ?
    C25 C24 O214 N21 . . . . 80.9(2) ?
    C23 C24 O214 N21 . . . . -42.1(3) ?
    C29A N21 O214 C24 . . . . -72.2(2) ?
    C22 N21 O214 C24 . . . . 46.9(2) ?
    C23 C22 C221 C226 . . . . 73.8(3) ?
    N21 C22 C221 C226 . . . . -44.4(3) ?
    C23 C22 C221 C222 . . . . -105.0(3) ?
    N21 C22 C221 C222 . . . . 136.8(2) ?
    C226 C221 C222 C223 . . . . 1.2(4) ?
    C22 C221 C222 C223 . . . . 180.0(3) ?
    C221 C222 C223 C224 . . . . 0.9(4) ?
    C222 C223 C224 C225 . . . . -2.1(4) ?
    C222 C223 C224 Cl24 . . . . 178.9(2) ?
    C223 C224 C225 C226 . . . . 1.4(4) ?
    Cl24 C224 C225 C226 . . . . -179.7(2) ?
    C222 C221 C226 C225 . . . . -1.9(4) ?
    C22 C221 C226 C225 . . . . 179.2(2) ?
    C224 C225 C226 C221 . . . . 0.7(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C22 H22 O114 3_566 1.00 2.37 3.357(3) 168 no
    C22 H22 N11 3_566 1.00 2.56 3.442(3) 147 no
    C125 H125 O114 3_566 0.95 2.38 3.248(3) 152 no
    C225 H225 O214 3_656 0.95 2.50 3.428(3) 164 no
    C23 H23B Cg3 3_556 0.99 2.78 3.596(3) 140 no
data_III
_chemical_name_systematic
;
2-exo-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-1,4- epoxy-1-benzazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H17 N O'
_chemical_formula_sum     'C17 H17 N O'
_chemical_formula_iupac     'C17 H17 N O'
_chemical_formula_weight     251.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.9966(17)
_cell_length_b     23.691(10)
_cell_length_c     10.6323(8)
_cell_angle_alpha     90.00
_cell_angle_beta     111.661(8)
_cell_angle_gamma     90.00
_cell_volume     2574.3(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5901
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.297
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1072
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.965
_exptl_absorpt_correction_T_max     0.989
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker-Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     30931
_diffrn_reflns_av_R_equivalents     0.0747
_diffrn_reflns_av_sigmaI/netI     0.0550
_diffrn_reflns_theta_min     2.63
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4790
_reflns_number_gt     3352
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0940
_refine_ls_R_factor_gt     0.0565
_refine_ls_wR_factor_gt     0.1013
_refine_ls_wR_factor_ref     0.1144
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     4790
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0254P)²+2.2514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.231
_refine_diff_density_min     -0.314
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N11 0.81171(17) 0.21064(8) 0.73917(18) 0.0197(4) Uani d . 1 . .
    C C12 0.7860(2) 0.24867(9) 0.6223(2) 0.0179(5) Uani d . 1 . .
    H H12 0.8433 0.2375 0.5721 0.022 Uiso calc R 1 . .
    C C13 0.6415(2) 0.23634(10) 0.5326(2) 0.0224(5) Uani d . 1 . .
    H H13A 0.5918 0.2718 0.5014 0.027 Uiso calc R 1 . .
    H H13B 0.6355 0.2133 0.4528 0.027 Uiso calc R 1 . .
    C C14 0.5914(2) 0.20392(10) 0.6267(2) 0.0221(5) Uani d . 1 . .
    H H14 0.5044 0.2189 0.6208 0.027 Uiso calc R 1 . .
    C C15 0.5856(2) 0.14082(10) 0.6071(2) 0.0239(5) Uani d . 1 . .
    H H15A 0.5448 0.1232 0.6662 0.029 Uiso calc R 1 . .
    H H15B 0.5313 0.1317 0.5120 0.029 Uiso calc R 1 . .
    C C15A 0.7214(2) 0.11779(10) 0.6410(2) 0.0205(5) Uani d . 1 . .
    C C16 0.7457(2) 0.06293(10) 0.6132(2) 0.0235(5) Uani d . 1 . .
    H H16 0.6739 0.0383 0.5711 0.028 Uiso calc R 1 . .
    C C17 0.8714(2) 0.04290(10) 0.6446(2) 0.0253(6) Uani d . 1 . .
    H H17 0.8858 0.0050 0.6248 0.030 Uiso calc R 1 . .
    C C18 0.9761(2) 0.07880(10) 0.7055(2) 0.0242(6) Uani d . 1 . .
    H H18 1.0629 0.0656 0.7264 0.029 Uiso calc R 1 . .
    C C19 0.9548(2) 0.13349(10) 0.7359(2) 0.0207(5) Uani d . 1 . .
    H H19 1.0269 0.1579 0.7785 0.025 Uiso calc R 1 . .
    C C19A 0.8285(2) 0.15291(9) 0.7044(2) 0.0188(5) Uani d . 1 . .
    O O114 0.69003(15) 0.21449(7) 0.76042(15) 0.0240(4) Uani d . 1 . .
    C C121 0.8129(2) 0.30962(10) 0.6659(2) 0.0182(5) Uani d . 1 . .
    C C122 0.7903(2) 0.35101(10) 0.5679(2) 0.0211(5) Uani d . 1 . .
    H H122 0.7548 0.3405 0.4752 0.025 Uiso calc R 1 . .
    C C123 0.8179(2) 0.40730(10) 0.6011(2) 0.0232(5) Uani d . 1 . .
    C C124 0.8667(2) 0.42208(10) 0.7368(2) 0.0251(6) Uani d . 1 . .
    H H124 0.8844 0.4606 0.7619 0.030 Uiso calc R 1 . .
    C C125 0.8898(2) 0.38150(10) 0.8355(2) 0.0250(6) Uani d . 1 . .
    H H125 0.9236 0.3922 0.9281 0.030 Uiso calc R 1 . .
    C C126 0.8642(2) 0.32529(10) 0.8008(2) 0.0229(5) Uani d . 1 . .
    H H126 0.8819 0.2974 0.8695 0.027 Uiso calc R 1 . .
    C C127 0.7991(3) 0.45081(11) 0.4928(3) 0.0321(6) Uani d . 1 . .
    H H12A 0.8392 0.4375 0.4298 0.048 Uiso calc R 1 . .
    H H12B 0.8404 0.4863 0.5343 0.048 Uiso calc R 1 . .
    H H12C 0.7053 0.4570 0.4435 0.048 Uiso calc R 1 . .
    N N21 0.30859(17) 0.28295(8) 0.60314(18) 0.0201(4) Uani d . 1 . .
    C C22 0.2739(2) 0.24751(10) 0.7003(2) 0.0197(5) Uani d . 1 . .
    H H22 0.3315 0.2578 0.7948 0.024 Uiso calc R 1 . .
    C C23 0.1305(2) 0.26429(10) 0.6764(2) 0.0241(6) Uani d . 1 . .
    H H23A 0.0719 0.2310 0.6506 0.029 Uiso calc R 1 . .
    H H23B 0.1242 0.2817 0.7585 0.029 Uiso calc R 1 . .
    C C24 0.0965(2) 0.30647(10) 0.5615(2) 0.0215(5) Uani d . 1 . .
    H H24 0.0034 0.3014 0.4992 0.026 Uiso calc R 1 . .
    C C25 0.1210(2) 0.36732(10) 0.6061(2) 0.0237(5) Uani d . 1 . .
    H H25A 0.0777 0.3924 0.5279 0.028 Uiso calc R 1 . .
    H H25B 0.0830 0.3751 0.6755 0.028 Uiso calc R 1 . .
    C C25A 0.2654(2) 0.37945(10) 0.6635(2) 0.0201(5) Uani d . 1 . .
    C C26 0.3140(2) 0.43159(10) 0.7172(2) 0.0228(5) Uani d . 1 . .
    H H26 0.2550 0.4604 0.7199 0.027 Uiso calc R 1 . .
    C C27 0.4465(2) 0.44255(10) 0.7669(2) 0.0246(6) Uani d . 1 . .
    H H27 0.4783 0.4785 0.8042 0.030 Uiso calc R 1 . .
    C C28 0.5324(2) 0.40104(10) 0.7621(2) 0.0247(6) Uani d . 1 . .
    H H28 0.6237 0.4085 0.7957 0.030 Uiso calc R 1 . .
    C C29 0.4862(2) 0.34877(10) 0.7087(2) 0.0231(5) Uani d . 1 . .
    H H29 0.5456 0.3202 0.7055 0.028 Uiso calc R 1 . .
    C C29A 0.3535(2) 0.33808(9) 0.6599(2) 0.0188(5) Uani d . 1 . .
    O O214 0.18323(14) 0.29124(7) 0.49351(14) 0.0211(4) Uani d . 1 . .
    C C221 0.2867(2) 0.18544(10) 0.6790(2) 0.0204(5) Uani d . 1 . .
    C C222 0.3379(2) 0.14974(10) 0.7889(2) 0.0219(5) Uani d . 1 . .
    H H222 0.3699 0.1654 0.8774 0.026 Uiso calc R 1 . .
    C C223 0.3441(2) 0.09165(10) 0.7742(2) 0.0232(5) Uani d . 1 . .
    C C224 0.2974(2) 0.06926(10) 0.6450(2) 0.0242(6) Uani d . 1 . .
    H H224 0.2997 0.0296 0.6326 0.029 Uiso calc R 1 . .
    C C225 0.2474(2) 0.10442(10) 0.5339(2) 0.0281(6) Uani d . 1 . .
    H H225 0.2165 0.0887 0.4454 0.034 Uiso calc R 1 . .
    C C226 0.2420(2) 0.16175(10) 0.5499(2) 0.0266(6) Uani d . 1 . .
    H H226 0.2076 0.1854 0.4726 0.032 Uiso calc R 1 . .
    C C227 0.4015(3) 0.05477(11) 0.8967(3) 0.0351(7) Uani d . 1 . .
    H H22A 0.3899 0.0150 0.8692 0.053 Uiso calc R 1 . .
    H H22B 0.3570 0.0622 0.9597 0.053 Uiso calc R 1 . .
    H H22C 0.4950 0.0630 0.9413 0.053 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N11 O114 . 1.440(2) ?
    N11 C19A . 1.446(3) ?
    N11 C12 . 1.475(3) ?
    C12 C121 . 1.512(3) ?
    C12 C13 . 1.550(3) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.517(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 O114 . 1.456(3) ?
    C14 C15 . 1.508(3) ?
    C14 H14 . 1.0000 ?
    C15 C15A . 1.504(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15A C16 . 1.381(3) ?
    C15A C19A . 1.395(3) ?
    C16 C17 . 1.380(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.385(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.376(3) ?
    C18 H18 . 0.9500 ?
    C19 C19A . 1.382(3) ?
    C19 H19 . 0.9500 ?
    C121 C126 . 1.384(3) ?
    C121 C122 . 1.385(3) ?
    C122 C123 . 1.384(3) ?
    C122 H122 . 0.9500 ?
    C123 C124 . 1.386(3) ?
    C123 C127 . 1.502(3) ?
    C124 C125 . 1.376(3) ?
    C124 H124 . 0.9500 ?
    C125 C126 . 1.383(3) ?
    C125 H125 . 0.9500 ?
    C126 H126 . 0.9500 ?
    C127 H12A . 0.9800 ?
    C127 H12B . 0.9800 ?
    C127 H12C . 0.9800 ?
    N21 C29A . 1.447(3) ?
    N21 O214 . 1.453(2) ?
    N21 C22 . 1.487(3) ?
    C22 C221 . 1.502(3) ?
    C22 C23 . 1.553(3) ?
    C22 H22 . 1.0000 ?
    C23 C24 . 1.514(3) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 O214 . 1.440(3) ?
    C24 C25 . 1.510(3) ?
    C24 H24 . 1.0000 ?
    C25 C25A . 1.504(3) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C25A C26 . 1.383(3) ?
    C25A C29A . 1.388(3) ?
    C26 C27 . 1.378(3) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.378(3) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.379(3) ?
    C28 H28 . 0.9500 ?
    C29 C29A . 1.380(3) ?
    C29 H29 . 0.9500 ?
    C221 C222 . 1.383(3) ?
    C221 C226 . 1.394(3) ?
    C222 C223 . 1.390(3) ?
    C222 H222 . 0.9500 ?
    C223 C224 . 1.382(3) ?
    C223 C227 . 1.501(3) ?
    C224 C225 . 1.383(3) ?
    C224 H224 . 0.9500 ?
    C225 C226 . 1.373(3) ?
    C225 H225 . 0.9500 ?
    C226 H226 . 0.9500 ?
    C227 H22A . 0.9800 ?
    C227 H22B . 0.9800 ?
    C227 H22C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O114 N11 C19A . . 108.27(16) ?
    O114 N11 C12 . . 101.15(16) ?
    C19A N11 C12 . . 111.43(17) ?
    N11 C12 C121 . . 111.72(18) ?
    N11 C12 C13 . . 103.73(17) ?
    C121 C12 C13 . . 114.13(19) ?
    N11 C12 H12 . . 109.0 ?
    C121 C12 H12 . . 109.0 ?
    C13 C12 H12 . . 109.0 ?
    C14 C13 C12 . . 103.23(17) ?
    C14 C13 H13A . . 111.1 ?
    C12 C13 H13A . . 111.1 ?
    C14 C13 H13B . . 111.1 ?
    C12 C13 H13B . . 111.1 ?
    H13A C13 H13B . . 109.1 ?
    O114 C14 C15 . . 106.49(18) ?
    O114 C14 C13 . . 103.66(17) ?
    C15 C14 C13 . . 114.7(2) ?
    O114 C14 H14 . . 110.6 ?
    C15 C14 H14 . . 110.6 ?
    C13 C14 H14 . . 110.6 ?
    C15A C15 C14 . . 109.81(19) ?
    C15A C15 H15A . . 109.7 ?
    C14 C15 H15A . . 109.7 ?
    C15A C15 H15B . . 109.7 ?
    C14 C15 H15B . . 109.7 ?
    H15A C15 H15B . . 108.2 ?
    C16 C15A C19A . . 118.0(2) ?
    C16 C15A C15 . . 122.9(2) ?
    C19A C15A C15 . . 119.1(2) ?
    C17 C16 C15A . . 121.8(2) ?
    C17 C16 H16 . . 119.1 ?
    C15A C16 H16 . . 119.1 ?
    C16 C17 C18 . . 119.2(2) ?
    C16 C17 H17 . . 120.4 ?
    C18 C17 H17 . . 120.4 ?
    C19 C18 C17 . . 120.3(2) ?
    C19 C18 H18 . . 119.9 ?
    C17 C18 H18 . . 119.9 ?
    C18 C19 C19A . . 120.0(2) ?
    C18 C19 H19 . . 120.0 ?
    C19A C19 H19 . . 120.0 ?
    C19 C19A C15A . . 120.8(2) ?
    C19 C19A N11 . . 117.7(2) ?
    C15A C19A N11 . . 121.5(2) ?
    N11 O114 C14 . . 103.67(15) ?
    C126 C121 C122 . . 118.8(2) ?
    C126 C121 C12 . . 122.2(2) ?
    C122 C121 C12 . . 119.0(2) ?
    C123 C122 C121 . . 121.9(2) ?
    C123 C122 H122 . . 119.0 ?
    C121 C122 H122 . . 119.0 ?
    C122 C123 C124 . . 118.2(2) ?
    C122 C123 C127 . . 120.7(2) ?
    C124 C123 C127 . . 121.0(2) ?
    C125 C124 C123 . . 120.6(2) ?
    C125 C124 H124 . . 119.7 ?
    C123 C124 H124 . . 119.7 ?
    C124 C125 C126 . . 120.5(2) ?
    C124 C125 H125 . . 119.8 ?
    C126 C125 H125 . . 119.8 ?
    C125 C126 C121 . . 120.0(2) ?
    C125 C126 H126 . . 120.0 ?
    C121 C126 H126 . . 120.0 ?
    C123 C127 H12A . . 109.5 ?
    C123 C127 H12B . . 109.5 ?
    H12A C127 H12B . . 109.5 ?
    C123 C127 H12C . . 109.5 ?
    H12A C127 H12C . . 109.5 ?
    H12B C127 H12C . . 109.5 ?
    C29A N21 O214 . . 106.81(16) ?
    C29A N21 C22 . . 110.82(17) ?
    O214 N21 C22 . . 102.88(15) ?
    N21 C22 C221 . . 112.66(18) ?
    N21 C22 C23 . . 104.33(17) ?
    C221 C22 C23 . . 111.84(19) ?
    N21 C22 H22 . . 109.3 ?
    C221 C22 H22 . . 109.3 ?
    C23 C22 H22 . . 109.3 ?
    C24 C23 C22 . . 103.56(18) ?
    C24 C23 H23A . . 111.0 ?
    C22 C23 H23A . . 111.0 ?
    C24 C23 H23B . . 111.0 ?
    C22 C23 H23B . . 111.0 ?
    H23A C23 H23B . . 109.0 ?
    O214 C24 C25 . . 108.78(18) ?
    O214 C24 C23 . . 103.15(17) ?
    C25 C24 C23 . . 114.5(2) ?
    O214 C24 H24 . . 110.1 ?
    C25 C24 H24 . . 110.1 ?
    C23 C24 H24 . . 110.1 ?
    C25A C25 C24 . . 110.44(19) ?
    C25A C25 H25A . . 109.6 ?
    C24 C25 H25A . . 109.6 ?
    C25A C25 H25B . . 109.6 ?
    C24 C25 H25B . . 109.6 ?
    H25A C25 H25B . . 108.1 ?
    C26 C25A C29A . . 118.4(2) ?
    C26 C25A C25 . . 121.8(2) ?
    C29A C25A C25 . . 119.8(2) ?
    C27 C26 C25A . . 121.3(2) ?
    C27 C26 H26 . . 119.4 ?
    C25A C26 H26 . . 119.4 ?
    C28 C27 C26 . . 119.6(2) ?
    C28 C27 H27 . . 120.2 ?
    C26 C27 H27 . . 120.2 ?
    C27 C28 C29 . . 120.2(2) ?
    C27 C28 H28 . . 119.9 ?
    C29 C28 H28 . . 119.9 ?
    C28 C29 C29A . . 119.8(2) ?
    C28 C29 H29 . . 120.1 ?
    C29A C29 H29 . . 120.1 ?
    C29 C29A C25A . . 120.8(2) ?
    C29 C29A N21 . . 118.2(2) ?
    C25A C29A N21 . . 121.0(2) ?
    C24 O214 N21 . . 103.84(15) ?
    C222 C221 C226 . . 118.1(2) ?
    C222 C221 C22 . . 120.2(2) ?
    C226 C221 C22 . . 121.6(2) ?
    C221 C222 C223 . . 122.1(2) ?
    C221 C222 H222 . . 118.9 ?
    C223 C222 H222 . . 118.9 ?
    C224 C223 C222 . . 118.5(2) ?
    C224 C223 C227 . . 121.5(2) ?
    C222 C223 C227 . . 120.1(2) ?
    C223 C224 C225 . . 120.2(2) ?
    C223 C224 H224 . . 119.9 ?
    C225 C224 H224 . . 119.9 ?
    C226 C225 C224 . . 120.8(2) ?
    C226 C225 H225 . . 119.6 ?
    C224 C225 H225 . . 119.6 ?
    C225 C226 C221 . . 120.3(2) ?
    C225 C226 H226 . . 119.8 ?
    C221 C226 H226 . . 119.8 ?
    C223 C227 H22A . . 109.5 ?
    C223 C227 H22B . . 109.5 ?
    H22A C227 H22B . . 109.5 ?
    C223 C227 H22C . . 109.5 ?
    H22A C227 H22C . . 109.5 ?
    H22B C227 H22C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O114 N11 C12 C121 . . . . 84.18(19) ?
    C19A N11 C12 C121 . . . . -160.95(17) ?
    O114 N11 C12 C13 . . . . -39.2(2) ?
    C19A N11 C12 C13 . . . . 75.7(2) ?
    N11 C12 C13 C14 . . . . 14.4(2) ?
    C121 C12 C13 C14 . . . . -107.3(2) ?
    C12 C13 C14 O114 . . . . 15.4(2) ?
    C12 C13 C14 C15 . . . . -100.3(2) ?
    O114 C14 C15 C15A . . . . -49.7(2) ?
    C13 C14 C15 C15A . . . . 64.3(2) ?
    C14 C15 C15A C16 . . . . -169.8(2) ?
    C14 C15 C15A C19A . . . . 10.7(3) ?
    C19A C15A C16 C17 . . . . -0.9(3) ?
    C15 C15A C16 C17 . . . . 179.6(2) ?
    C15A C16 C17 C18 . . . . -0.2(4) ?
    C16 C17 C18 C19 . . . . 0.9(3) ?
    C17 C18 C19 C19A . . . . -0.6(3) ?
    C18 C19 C19A C15A . . . . -0.4(3) ?
    C18 C19 C19A N11 . . . . 179.7(2) ?
    C16 C15A C19A C19 . . . . 1.2(3) ?
    C15 C15A C19A C19 . . . . -179.3(2) ?
    C16 C15A C19A N11 . . . . -179.0(2) ?
    C15 C15A C19A N11 . . . . 0.5(3) ?
    O114 N11 C19A C19 . . . . -152.61(18) ?
    C12 N11 C19A C19 . . . . 97.0(2) ?
    O114 N11 C19A C15A . . . . 27.5(3) ?
    C12 N11 C19A C15A . . . . -82.8(2) ?
    C19A N11 O114 C14 . . . . -66.59(19) ?
    C12 N11 O114 C14 . . . . 50.62(19) ?
    C15 C14 O114 N11 . . . . 80.29(19) ?
    C13 C14 O114 N11 . . . . -41.0(2) ?
    N11 C12 C121 C126 . . . . 4.3(3) ?
    C13 C12 C121 C126 . . . . 121.5(2) ?
    N11 C12 C121 C122 . . . . -178.32(19) ?
    C13 C12 C121 C122 . . . . -61.0(3) ?
    C126 C121 C122 C123 . . . . 0.2(3) ?
    C12 C121 C122 C123 . . . . -177.3(2) ?
    C121 C122 C123 C124 . . . . -1.5(3) ?
    C121 C122 C123 C127 . . . . 176.7(2) ?
    C122 C123 C124 C125 . . . . 1.5(3) ?
    C127 C123 C124 C125 . . . . -176.7(2) ?
    C123 C124 C125 C126 . . . . -0.2(4) ?
    C124 C125 C126 C121 . . . . -1.1(3) ?
    C122 C121 C126 C125 . . . . 1.1(3) ?
    C12 C121 C126 C125 . . . . 178.5(2) ?
    C29A N21 C22 C221 . . . . -153.64(18) ?
    O214 N21 C22 C221 . . . . 92.51(19) ?
    C29A N21 C22 C23 . . . . 84.8(2) ?
    O214 N21 C22 C23 . . . . -29.0(2) ?
    N21 C22 C23 C24 . . . . 2.4(2) ?
    C221 C22 C23 C24 . . . . -119.6(2) ?
    C22 C23 C24 O214 . . . . 25.2(2) ?
    C22 C23 C24 C25 . . . . -92.8(2) ?
    O214 C24 C25 C25A . . . . -42.2(2) ?
    C23 C24 C25 C25A . . . . 72.6(2) ?
    C24 C25 C25A C26 . . . . -177.0(2) ?
    C24 C25 C25A C29A . . . . 4.7(3) ?
    C29A C25A C26 C27 . . . . -0.4(3) ?
    C25 C25A C26 C27 . . . . -178.6(2) ?
    C25A C26 C27 C28 . . . . 0.6(3) ?
    C26 C27 C28 C29 . . . . -0.4(3) ?
    C27 C28 C29 C29A . . . . 0.0(3) ?
    C28 C29 C29A C25A . . . . 0.2(3) ?
    C28 C29 C29A N21 . . . . 179.2(2) ?
    C26 C25A C29A C29 . . . . 0.0(3) ?
    C25 C25A C29A C29 . . . . 178.2(2) ?
    C26 C25A C29A N21 . . . . -179.0(2) ?
    C25 C25A C29A N21 . . . . -0.8(3) ?
    O214 N21 C29A C29 . . . . -145.90(19) ?
    C22 N21 C29A C29 . . . . 102.8(2) ?
    O214 N21 C29A C25A . . . . 33.1(3) ?
    C22 N21 C29A C25A . . . . -78.2(2) ?
    C25 C24 O214 N21 . . . . 77.0(2) ?
    C23 C24 O214 N21 . . . . -44.9(2) ?
    C29A N21 O214 C24 . . . . -70.01(19) ?
    C22 N21 O214 C24 . . . . 46.73(19) ?
    N21 C22 C221 C222 . . . . 139.9(2) ?
    C23 C22 C221 C222 . . . . -103.0(2) ?
    N21 C22 C221 C226 . . . . -43.4(3) ?
    C23 C22 C221 C226 . . . . 73.8(3) ?
    C226 C221 C222 C223 . . . . -0.9(3) ?
    C22 C221 C222 C223 . . . . 175.9(2) ?
    C221 C222 C223 C224 . . . . 0.0(4) ?
    C221 C222 C223 C227 . . . . 179.6(2) ?
    C222 C223 C224 C225 . . . . 0.8(3) ?
    C227 C223 C224 C225 . . . . -178.7(2) ?
    C223 C224 C225 C226 . . . . -0.8(4) ?
    C224 C225 C226 C221 . . . . -0.2(4) ?
    C222 C221 C226 C225 . . . . 1.0(3) ?
    C22 C221 C226 C225 . . . . -175.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C14 H14 N21 . 1.00 2.58 3.559(3) 165 no
    C122 H122 O114 4_565 0.95 2.49 3.413(3) 163 no
    C15 H15A Cg3 . 0.99 2.76 3.495(3) 132 no
    C25 H25B Cg4 1_455 0.99 2.79 3.586(3) 138 no
data_IV
_chemical_name_systematic
;
7-bromo-2-exo-phenyl-2,3,4,5-tetrahydro-1H-1,4- epoxy-1-benzazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 Br N O'
_chemical_formula_sum     'C16 H14 Br N O'
_chemical_formula_iupac     'C16 H14 Br N O'
_chemical_formula_weight     316.19
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     5.5214(3)
_cell_length_b     10.2982(12)
_cell_length_c     22.900(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1302.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2989
_cell_measurement_theta_min     3.32
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.613
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     3.147
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.471
_exptl_absorpt_correction_T_max     0.568
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker-Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     14968
_diffrn_reflns_av_R_equivalents     0.0508
_diffrn_reflns_av_sigmaI/netI     0.0451
_diffrn_reflns_theta_min     3.32
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2989
_reflns_number_gt     2587
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0458
_refine_ls_R_factor_gt     0.0324
_refine_ls_wR_factor_gt     0.0598
_refine_ls_wR_factor_ref     0.0639
_refine_ls_goodness_of_fit_ref     1.070
_refine_ls_restrained_S_all     1.070
_refine_ls_number_reflns     2989
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0249P)²+0.4327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.506
_refine_diff_density_min     -0.496
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1228 Bijvoet pairs'
_refine_ls_abs_structure_Flack     0.497(9)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'Sir2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.5898(4) 0.3932(2) 0.11111(10) 0.0173(6) Uani d . 1 . .
    C C2 0.4507(5) 0.3346(3) 0.16044(12) 0.0184(6) Uani d . 1 . .
    H H2 0.3993 0.4052 0.1877 0.022 Uiso calc R 1 . .
    C C3 0.2250(5) 0.2768(3) 0.13127(12) 0.0202(7) Uani d . 1 . .
    H H3A 0.2045 0.1844 0.1420 0.024 Uiso calc R 1 . .
    H H3B 0.0776 0.3253 0.1427 0.024 Uiso calc R 1 . .
    C C4 0.2749(5) 0.2913(3) 0.06604(13) 0.0209(6) Uani d . 1 . .
    H H4 0.2236 0.2114 0.0445 0.025 Uiso calc R 1 . .
    C C5 0.1627(6) 0.4097(3) 0.03939(12) 0.0200(6) Uani d . 1 . .
    H H5A -0.0129 0.4113 0.0480 0.024 Uiso calc R 1 . .
    H H5B 0.1834 0.4073 -0.0035 0.024 Uiso calc R 1 . .
    C C5A 0.2808(5) 0.5297(3) 0.06365(13) 0.0166(6) Uani d . 1 . .
    C C6 0.1900(6) 0.6529(3) 0.05266(11) 0.0176(6) Uani d . 1 . .
    H H6 0.0468 0.6632 0.0301 0.021 Uiso calc R 1 . .
    C C7 0.3075(6) 0.7595(3) 0.07449(11) 0.0186(6) Uani d . 1 . .
    Br Br7 0.17334(6) 0.92624(3) 0.061526(13) 0.02630(9) Uani d . 1 . .
    C C8 0.5181(6) 0.7489(3) 0.10599(13) 0.0222(7) Uani d . 1 . .
    H H8 0.5993 0.8241 0.1200 0.027 Uiso calc R 1 . .
    C C9 0.6092(5) 0.6266(3) 0.11685(13) 0.0218(7) Uani d . 1 . .
    H H9 0.7550 0.6170 0.1384 0.026 Uiso calc R 1 . .
    C C9A 0.4890(5) 0.5182(3) 0.09649(12) 0.0171(6) Uani d . 1 . .
    O O14 0.5358(3) 0.30644(17) 0.06365(9) 0.0203(4) Uani d . 1 . .
    C C21 0.6083(5) 0.2402(3) 0.19305(12) 0.0179(7) Uani d . 1 . .
    C C22 0.7003(6) 0.2751(3) 0.24663(12) 0.0229(7) Uani d . 1 . .
    H H22 0.6579 0.3567 0.2631 0.027 Uiso calc R 1 . .
    C C23 0.8526(7) 0.1935(3) 0.27659(12) 0.0280(7) Uani d . 1 . .
    H H23 0.9160 0.2196 0.3133 0.034 Uiso calc R 1 . .
    C C24 0.9143(5) 0.0745(3) 0.25392(13) 0.0249(7) Uani d . 1 . .
    H H24 1.0195 0.0181 0.2748 0.030 Uiso calc R 1 . .
    C C25 0.8220(6) 0.0382(3) 0.20080(12) 0.0248(7) Uani d . 1 . .
    H H25 0.8632 -0.0439 0.1848 0.030 Uiso calc R 1 . .
    C C26 0.6703(7) 0.1198(3) 0.17051(13) 0.0231(6) Uani d . 1 . .
    H H26 0.6072 0.0934 0.1338 0.028 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 O14 . 1.438(3) ?
    N1 C9A . 1.441(4) ?
    N1 C2 . 1.494(4) ?
    C2 C21 . 1.503(4) ?
    C2 C3 . 1.533(4) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.526(4) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 O14 . 1.450(3) ?
    C4 C5 . 1.498(4) ?
    C4 H4 . 1.0000 ?
    C5 C5A . 1.504(4) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C5A C9A . 1.379(4) ?
    C5A C6 . 1.387(4) ?
    C6 C7 . 1.370(4) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.373(4) ?
    C7 Br7 . 1.893(3) ?
    C8 C9 . 1.378(4) ?
    C8 H8 . 0.9500 ?
    C9 C9A . 1.380(4) ?
    C9 H9 . 0.9500 ?
    C21 C22 . 1.376(4) ?
    C21 C26 . 1.386(4) ?
    C22 C23 . 1.373(4) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.374(4) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.371(4) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.374(4) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O14 N1 C9A . . 107.4(2) ?
    O14 N1 C2 . . 102.3(2) ?
    C9A N1 C2 . . 109.7(2) ?
    N1 C2 C21 . . 109.8(2) ?
    N1 C2 C3 . . 104.2(2) ?
    C21 C2 C3 . . 115.9(3) ?
    N1 C2 H2 . . 108.9 ?
    C21 C2 H2 . . 108.9 ?
    C3 C2 H2 . . 108.9 ?
    C4 C3 C2 . . 104.0(2) ?
    C4 C3 H3A . . 111.0 ?
    C2 C3 H3A . . 111.0 ?
    C4 C3 H3B . . 111.0 ?
    C2 C3 H3B . . 111.0 ?
    H3A C3 H3B . . 109.0 ?
    O14 C4 C5 . . 107.9(2) ?
    O14 C4 C3 . . 103.1(2) ?
    C5 C4 C3 . . 113.8(2) ?
    O14 C4 H4 . . 110.6 ?
    C5 C4 H4 . . 110.6 ?
    C3 C4 H4 . . 110.6 ?
    C4 C5 C5A . . 109.8(2) ?
    C4 C5 H5A . . 109.7 ?
    C5A C5 H5A . . 109.7 ?
    C4 C5 H5B . . 109.7 ?
    C5A C5 H5B . . 109.7 ?
    H5A C5 H5B . . 108.2 ?
    C9A C5A C6 . . 118.6(2) ?
    C9A C5A C5 . . 119.5(2) ?
    C6 C5A C5 . . 121.9(2) ?
    C7 C6 C5A . . 119.7(3) ?
    C7 C6 H6 . . 120.1 ?
    C5A C6 H6 . . 120.1 ?
    C6 C7 C8 . . 121.9(3) ?
    C6 C7 Br7 . . 119.0(2) ?
    C8 C7 Br7 . . 119.1(2) ?
    C7 C8 C9 . . 118.5(3) ?
    C7 C8 H8 . . 120.8 ?
    C9 C8 H8 . . 120.8 ?
    C8 C9 C9A . . 120.2(3) ?
    C8 C9 H9 . . 119.9 ?
    C9A C9 H9 . . 119.9 ?
    C5A C9A C9 . . 121.0(3) ?
    C5A C9A N1 . . 121.7(3) ?
    C9 C9A N1 . . 117.3(2) ?
    N1 O14 C4 . . 104.1(2) ?
    C22 C21 C26 . . 118.3(3) ?
    C22 C21 C2 . . 119.2(3) ?
    C26 C21 C2 . . 122.4(3) ?
    C23 C22 C21 . . 120.8(3) ?
    C23 C22 H22 . . 119.6 ?
    C21 C22 H22 . . 119.6 ?
    C22 C23 C24 . . 120.6(3) ?
    C22 C23 H23 . . 119.7 ?
    C24 C23 H23 . . 119.7 ?
    C25 C24 C23 . . 119.1(3) ?
    C25 C24 H24 . . 120.5 ?
    C23 C24 H24 . . 120.5 ?
    C24 C25 C26 . . 120.6(3) ?
    C24 C25 H25 . . 119.7 ?
    C26 C25 H25 . . 119.7 ?
    C25 C26 C21 . . 120.6(3) ?
    C25 C26 H26 . . 119.7 ?
    C21 C26 H26 . . 119.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O14 N1 C2 C21 . . . . 91.3(2) ?
    C9A N1 C2 C21 . . . . -154.9(2) ?
    O14 N1 C2 C3 . . . . -33.4(3) ?
    C9A N1 C2 C3 . . . . 80.4(3) ?
    N1 C2 C3 C4 . . . . 7.9(3) ?
    C21 C2 C3 C4 . . . . -112.9(3) ?
    C2 C3 C4 O14 . . . . 20.1(3) ?
    C2 C3 C4 C5 . . . . -96.5(3) ?
    O14 C4 C5 C5A . . . . -47.0(3) ?
    C3 C4 C5 C5A . . . . 66.7(3) ?
    C4 C5 C5A C9A . . . . 10.8(4) ?
    C4 C5 C5A C6 . . . . -170.9(3) ?
    C9A C5A C6 C7 . . . . -0.1(4) ?
    C5 C5A C6 C7 . . . . -178.3(3) ?
    C5A C6 C7 C8 . . . . 1.7(4) ?
    C5A C6 C7 Br7 . . . . -177.6(2) ?
    C6 C7 C8 C9 . . . . -1.5(4) ?
    Br7 C7 C8 C9 . . . . 177.7(2) ?
    C7 C8 C9 C9A . . . . -0.3(5) ?
    C6 C5A C9A C9 . . . . -1.7(4) ?
    C5 C5A C9A C9 . . . . 176.6(3) ?
    C6 C5A C9A N1 . . . . 178.1(3) ?
    C5 C5A C9A N1 . . . . -3.6(4) ?
    C8 C9 C9A C5A . . . . 1.9(5) ?
    C8 C9 C9A N1 . . . . -178.0(3) ?
    O14 N1 C9A C5A . . . . 32.0(3) ?
    C2 N1 C9A C5A . . . . -78.5(3) ?
    O14 N1 C9A C9 . . . . -148.2(2) ?
    C2 N1 C9A C9 . . . . 101.3(3) ?
    C9A N1 O14 C4 . . . . -67.6(3) ?
    C2 N1 O14 C4 . . . . 47.9(2) ?
    C5 C4 O14 N1 . . . . 78.3(3) ?
    C3 C4 O14 N1 . . . . -42.4(2) ?
    N1 C2 C21 C22 . . . . 105.1(3) ?
    C3 C2 C21 C22 . . . . -137.3(3) ?
    N1 C2 C21 C26 . . . . -73.3(4) ?
    C3 C2 C21 C26 . . . . 44.4(4) ?
    C26 C21 C22 C23 . . . . 1.0(5) ?
    C2 C21 C22 C23 . . . . -177.4(3) ?
    C21 C22 C23 C24 . . . . -0.7(5) ?
    C22 C23 C24 C25 . . . . 0.1(5) ?
    C23 C24 C25 C26 . . . . 0.1(5) ?
    C24 C25 C26 C21 . . . . 0.1(5) ?
    C22 C21 C26 C25 . . . . -0.7(5) ?
    C2 C21 C26 C25 . . . . 177.6(3) ?
data_V
_chemical_name_systematic
;
2-exo-(4-bromophenyl)-7-chloro-2,3,4,5-
tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H13 Br Cl N O'
_chemical_formula_sum     'C16 H13 Br Cl N O'
_chemical_formula_iupac     'C16 H13 Br Cl N O'
_chemical_formula_weight     350.63
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.3626(16)
_cell_length_b     11.5436(13)
_cell_length_c     7.8832(13)
_cell_angle_alpha     90.00
_cell_angle_beta     96.080(11)
_cell_angle_gamma     90.00
_cell_volume     1390.1(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3182
_cell_measurement_theta_min     2.67
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.675
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     3.143
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.406
_exptl_absorpt_correction_T_max     0.470
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker-Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     19930
_diffrn_reflns_av_R_equivalents     0.0722
_diffrn_reflns_av_sigmaI/netI     0.0557
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3181
_reflns_number_gt     2267
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0738
_refine_ls_R_factor_gt     0.0411
_refine_ls_wR_factor_gt     0.0835
_refine_ls_wR_factor_ref     0.0948
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     3181
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0394P)²+1.0122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.860
_refine_diff_density_min     -0.561
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.30143(16) 0.6769(2) 0.6277(3) 0.0187(6) Uani d . 1 . .
    C C2 0.3352(2) 0.6274(3) 0.7960(4) 0.0195(7) Uani d . 1 . .
    H H2 0.3142 0.6749 0.8895 0.023 Uiso calc R 1 . .
    C C3 0.2933(2) 0.5067(3) 0.7941(4) 0.0228(7) Uani d . 1 . .
    H H3A 0.3366 0.4471 0.8363 0.027 Uiso calc R 1 . .
    H H3B 0.2436 0.5049 0.8646 0.027 Uiso calc R 1 . .
    C C4 0.26234(19) 0.4884(3) 0.6076(5) 0.0231(7) Uani d . 1 . .
    H H4 0.2803 0.4101 0.5700 0.028 Uiso calc R 1 . .
    C C5 0.16535(19) 0.5052(3) 0.5636(5) 0.0248(8) Uani d . 1 . .
    H H5A 0.1483 0.4830 0.4434 0.030 Uiso calc R 1 . .
    H H5B 0.1326 0.4559 0.6376 0.030 Uiso calc R 1 . .
    C C5A 0.1442(2) 0.6304(3) 0.5897(4) 0.0219(7) Uani d . 1 . .
    C C6 0.0584(2) 0.6685(3) 0.5793(5) 0.0293(8) Uani d . 1 . .
    H H6 0.0115 0.6150 0.5576 0.035 Uiso calc R 1 . .
    C C7 0.0414(2) 0.7832(4) 0.6002(5) 0.0313(9) Uani d . 1 . .
    Cl Cl7 -0.06685(6) 0.82971(10) 0.58244(15) 0.0525(3) Uani d . 1 . .
    C C8 0.1072(2) 0.8628(3) 0.6350(5) 0.0299(9) Uani d . 1 . .
    H H8 0.0940 0.9422 0.6511 0.036 Uiso calc R 1 . .
    C C9 0.1927(2) 0.8255(3) 0.6461(4) 0.0245(8) Uani d . 1 . .
    H H9 0.2391 0.8793 0.6699 0.029 Uiso calc R 1 . .
    C C9A 0.2110(2) 0.7102(3) 0.6229(4) 0.0193(7) Uani d . 1 . .
    O O14 0.30532(13) 0.57727(18) 0.5191(3) 0.0200(5) Uani d . 1 . .
    C C21 0.4338(2) 0.6283(3) 0.8113(4) 0.0194(7) Uani d . 1 . .
    C C22 0.4784(2) 0.7183(3) 0.8985(4) 0.0227(7) Uani d . 1 . .
    H H22 0.4466 0.7745 0.9547 0.027 Uiso calc R 1 . .
    C C23 0.5681(2) 0.7273(3) 0.9049(4) 0.0219(7) Uani d . 1 . .
    H H23 0.5982 0.7891 0.9653 0.026 Uiso calc R 1 . .
    C C24 0.6133(2) 0.6455(3) 0.8227(4) 0.0202(7) Uani d . 1 . .
    Br Br24 0.73587(2) 0.66277(3) 0.81935(4) 0.02365(12) Uani d . 1 . .
    C C25 0.5716(2) 0.5527(3) 0.7402(4) 0.0222(7) Uani d . 1 . .
    H H25 0.6038 0.4953 0.6871 0.027 Uiso calc R 1 . .
    C C26 0.4818(2) 0.5452(3) 0.7367(4) 0.0234(8) Uani d . 1 . .
    H H26 0.4522 0.4811 0.6813 0.028 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C9A . 1.438(4) ?
    N1 O14 . 1.438(3) ?
    N1 C2 . 1.487(4) ?
    C2 C21 . 1.506(4) ?
    C2 C3 . 1.534(4) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.511(5) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 O14 . 1.439(4) ?
    C4 C5 . 1.506(4) ?
    C4 H4 . 1.0000 ?
    C5 C5A . 1.499(5) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C5A C9A . 1.383(4) ?
    C5A C6 . 1.384(4) ?
    C6 C7 . 1.362(5) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.372(5) ?
    C7 Cl7 . 1.739(3) ?
    C8 C9 . 1.377(5) ?
    C8 H8 . 0.9500 ?
    C9 C9A . 1.377(4) ?
    C9 H9 . 0.9500 ?
    C21 C26 . 1.379(5) ?
    C21 C22 . 1.386(5) ?
    C22 C23 . 1.377(4) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.375(4) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.375(4) ?
    C24 Br24 . 1.897(3) ?
    C25 C26 . 1.380(4) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9A N1 O14 . . 107.4(2) ?
    C9A N1 C2 . . 111.8(2) ?
    O14 N1 C2 . . 101.0(2) ?
    N1 C2 C21 . . 108.8(3) ?
    N1 C2 C3 . . 103.5(2) ?
    C21 C2 C3 . . 115.1(3) ?
    N1 C2 H2 . . 109.7 ?
    C21 C2 H2 . . 109.7 ?
    C3 C2 H2 . . 109.7 ?
    C4 C3 C2 . . 102.9(3) ?
    C4 C3 H3A . . 111.2 ?
    C2 C3 H3A . . 111.2 ?
    C4 C3 H3B . . 111.2 ?
    C2 C3 H3B . . 111.2 ?
    H3A C3 H3B . . 109.1 ?
    O14 C4 C5 . . 106.9(3) ?
    O14 C4 C3 . . 105.0(2) ?
    C5 C4 C3 . . 114.1(3) ?
    O14 C4 H4 . . 110.2 ?
    C5 C4 H4 . . 110.2 ?
    C3 C4 H4 . . 110.2 ?
    C5A C5 C4 . . 108.4(3) ?
    C5A C5 H5A . . 110.0 ?
    C4 C5 H5A . . 110.0 ?
    C5A C5 H5B . . 110.0 ?
    C4 C5 H5B . . 110.0 ?
    H5A C5 H5B . . 108.4 ?
    C9A C5A C6 . . 118.8(3) ?
    C9A C5A C5 . . 120.0(3) ?
    C6 C5A C5 . . 121.2(3) ?
    C7 C6 C5A . . 119.7(3) ?
    C7 C6 H6 . . 120.1 ?
    C5A C6 H6 . . 120.1 ?
    C6 C7 C8 . . 121.9(3) ?
    C6 C7 Cl7 . . 119.0(3) ?
    C8 C7 Cl7 . . 119.2(3) ?
    C7 C8 C9 . . 118.8(3) ?
    C7 C8 H8 . . 120.6 ?
    C9 C8 H8 . . 120.6 ?
    C8 C9 C9A . . 120.0(3) ?
    C8 C9 H9 . . 120.0 ?
    C9A C9 H9 . . 120.0 ?
    C9 C9A C5A . . 120.8(3) ?
    C9 C9A N1 . . 117.7(3) ?
    C5A C9A N1 . . 121.5(3) ?
    N1 O14 C4 . . 103.3(2) ?
    C26 C21 C22 . . 118.3(3) ?
    C26 C21 C2 . . 122.7(3) ?
    C22 C21 C2 . . 119.0(3) ?
    C23 C22 C21 . . 121.0(3) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 118.9(3) ?
    C24 C23 H23 . . 120.5 ?
    C22 C23 H23 . . 120.5 ?
    C25 C24 C23 . . 121.6(3) ?
    C25 C24 Br24 . . 119.3(2) ?
    C23 C24 Br24 . . 119.1(2) ?
    C24 C25 C26 . . 118.2(3) ?
    C24 C25 H25 . . 120.9 ?
    C26 C25 H25 . . 120.9 ?
    C21 C26 C25 . . 121.8(3) ?
    C21 C26 H26 . . 119.1 ?
    C25 C26 H26 . . 119.1 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9A N1 C2 C21 . . . . -163.1(3) ?
    O14 N1 C2 C21 . . . . 83.0(3) ?
    C9A N1 C2 C3 . . . . 74.0(3) ?
    O14 N1 C2 C3 . . . . -39.9(3) ?
    N1 C2 C3 C4 . . . . 15.9(3) ?
    C21 C2 C3 C4 . . . . -102.7(3) ?
    C2 C3 C4 O14 . . . . 13.8(3) ?
    C2 C3 C4 C5 . . . . -102.9(3) ?
    O14 C4 C5 C5A . . . . -49.1(4) ?
    C3 C4 C5 C5A . . . . 66.5(4) ?
    C4 C5 C5A C9A . . . . 8.8(4) ?
    C4 C5 C5A C6 . . . . -172.0(3) ?
    C9A C5A C6 C7 . . . . 0.5(5) ?
    C5 C5A C6 C7 . . . . -178.7(3) ?
    C5A C6 C7 C8 . . . . -1.3(6) ?
    C5A C6 C7 Cl7 . . . . 178.7(3) ?
    C6 C7 C8 C9 . . . . 1.1(6) ?
    Cl7 C7 C8 C9 . . . . -179.0(3) ?
    C7 C8 C9 C9A . . . . -0.1(5) ?
    C8 C9 C9A C5A . . . . -0.6(5) ?
    C8 C9 C9A N1 . . . . 177.1(3) ?
    C6 C5A C9A C9 . . . . 0.4(5) ?
    C5 C5A C9A C9 . . . . 179.6(3) ?
    C6 C5A C9A N1 . . . . -177.2(3) ?
    C5 C5A C9A N1 . . . . 2.0(5) ?
    O14 N1 C9A C9 . . . . -150.5(3) ?
    C2 N1 C9A C9 . . . . 99.6(3) ?
    O14 N1 C9A C5A . . . . 27.2(4) ?
    C2 N1 C9A C5A . . . . -82.8(4) ?
    C9A N1 O14 C4 . . . . -67.4(3) ?
    C2 N1 O14 C4 . . . . 49.9(3) ?
    C5 C4 O14 N1 . . . . 81.6(3) ?
    C3 C4 O14 N1 . . . . -39.9(3) ?
    N1 C2 C21 C26 . . . . -80.3(4) ?
    C3 C2 C21 C26 . . . . 35.4(4) ?
    N1 C2 C21 C22 . . . . 97.3(3) ?
    C3 C2 C21 C22 . . . . -147.0(3) ?
    C26 C21 C22 C23 . . . . 2.6(5) ?
    C2 C21 C22 C23 . . . . -175.2(3) ?
    C21 C22 C23 C24 . . . . 0.2(5) ?
    C22 C23 C24 C25 . . . . -2.6(5) ?
    C22 C23 C24 Br24 . . . . 176.2(2) ?
    C23 C24 C25 C26 . . . . 2.1(5) ?
    Br24 C24 C25 C26 . . . . -176.6(2) ?
    C22 C21 C26 C25 . . . . -3.0(5) ?
    C2 C21 C26 C25 . . . . 174.6(3) ?
    C24 C25 C26 C21 . . . . 0.7(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C2 H2 N1 4_576 1.00 2.56 3.535(4) 164 no
    C25 H25 O14 3_666 0.95 2.40 3.290(4) 155 no
