##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_database_code_depnum_ccdc_archive     'CCDC 1012125'
_chemical_name_systematic
;\
Ethyl
4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-\
carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 Br N O3'
_chemical_formula_sum     'C21 H24 Br N O3'
_chemical_formula_iupac     'C21 H24 Br N O3'
_chemical_formula_weight     418.32
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c n'
_space_group_name_Hall     '-P 2n 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     18.0371(4)
_cell_length_b     15.4309(3)
_cell_length_c     14.2604(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3969.08(14)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9956
_cell_measurement_theta_min     2.25
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.264
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.133
_exptl_crystal_density_diffrn     1.400
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1728
_exptl_absorpt_coefficient_mu     2.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_shelx_estimated_absorpt_T_min     0.608
_shelx_estimated_absorpt_T_max     0.768
_exptl_absorpt_correction_T_min     0.9087
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.02
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     35271
_diffrn_reflns_av_R_equivalents     0.0377
_diffrn_reflns_theta_min     2.857
_diffrn_reflns_theta_max     27.499
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_refine_special_details
;
;
_reflns_number_total     4558
_reflns_number_gt     3391
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0663
_refine_ls_R_factor_gt     0.0424
_refine_ls_wR_factor_gt     0.0913
_refine_ls_wR_factor_ref     0.1010
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     4558
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0386P)²+5.4149P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.488
_refine_diff_density_min     -1.210
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.01835(2) 0.08589(2) 0.60206(2) 0.03911(12) Uani d 1 . .
    O O1 0.39646(10) -0.02836(11) 0.63323(11) 0.0200(4) Uani d 1 . .
    O O2 0.35587(10) 0.33300(11) 0.41638(12) 0.0213(4) Uani d 1 . .
    O O3 0.34556(10) 0.27791(11) 0.56159(11) 0.0213(4) Uani d 1 . .
    N N1 0.39491(12) 0.07392(13) 0.32412(14) 0.0190(5) Uani d 1 . .
    H H1 0.4013(16) 0.0634(19) 0.264(2) 0.027(8) Uiso d 1 . .
    C C2 0.38319(14) 0.15957(16) 0.35057(16) 0.0178(5) Uani d 1 . .
    C C3 0.36618(13) 0.17953(15) 0.44025(16) 0.0148(5) Uani d 1 . .
    C C4 0.35425(13) 0.10862(15) 0.51345(15) 0.0137(5) Uani d 1 . .
    H H4 0.3808 0.1260 0.5721 0.016 Uiso calc 1 . .
    C C5 0.40247(13) -0.04303(16) 0.54818(16) 0.0145(5) Uani d 1 . .
    C C6 0.43032(14) -0.13027(15) 0.51443(16) 0.0158(5) Uani d 1 . .
    H H6A 0.4101 -0.1757 0.5562 0.019 Uiso calc 1 . .
    H H6B 0.4850 -0.1314 0.5207 0.019 Uiso calc 1 . .
    C C7 0.41033(14) -0.15326(16) 0.41315(15) 0.0149(5) Uani d 1 . .
    C C8 0.42990(14) -0.07570(15) 0.35066(16) 0.0158(5) Uani d 1 . .
    H H8A 0.4845 -0.0721 0.3445 0.019 Uiso calc 1 . .
    H H8B 0.4090 -0.0854 0.2873 0.019 Uiso calc 1 . .
    C C9 0.40135(13) 0.00865(15) 0.38786(15) 0.0140(5) Uani d 1 . .
    C C10 0.38685(13) 0.02328(15) 0.47985(15) 0.0132(5) Uani d 1 . .
    C C11 0.32747(14) -0.17399(17) 0.40568(17) 0.0203(5) Uani d 1 . .
    H H11A 0.2985 -0.1230 0.4240 0.030 Uiso calc 1 . .
    H H11B 0.3154 -0.2225 0.4474 0.030 Uiso calc 1 . .
    H H11C 0.3154 -0.1898 0.3409 0.030 Uiso calc 1 . .
    C C12 0.45589(15) -0.23200(16) 0.38188(17) 0.0210(5) Uani d 1 . .
    H H12A 0.4444 -0.2455 0.3163 0.031 Uiso calc 1 . .
    H H12B 0.4435 -0.2819 0.4214 0.031 Uiso calc 1 . .
    H H12C 0.5088 -0.2189 0.3879 0.031 Uiso calc 1 . .
    C C13 0.39310(19) 0.22252(18) 0.27089(17) 0.0323(7) Uani d 1 . .
    H H13A 0.4131 0.1919 0.2163 0.048 Uiso calc 1 . .
    H H13B 0.4275 0.2684 0.2898 0.048 Uiso calc 1 . .
    H H13C 0.3451 0.2482 0.2547 0.048 Uiso calc 1 . .
    C C14 0.35600(13) 0.27062(16) 0.46787(17) 0.0166(5) Uani d 1 . .
    C C15 0.33581(17) 0.36583(17) 0.59609(18) 0.0254(6) Uani d 1 . .
    H H15A 0.2975 0.3962 0.5588 0.030 Uiso calc 1 . .
    H H15B 0.3829 0.3984 0.5907 0.030 Uiso calc 1 . .
    C C16 0.3126(3) 0.3606(2) 0.6959(2) 0.0582(12) Uani d 1 . .
    H H16A 0.2656 0.3291 0.7004 0.087 Uiso calc 1 . .
    H H16B 0.3062 0.4193 0.7210 0.087 Uiso calc 1 . .
    H H16C 0.3507 0.3301 0.7321 0.087 Uiso calc 1 . .
    C C17 0.27210(13) 0.09825(14) 0.53660(16) 0.0149(5) Uani d 1 . .
    C C18 0.22092(14) 0.08222(16) 0.46580(17) 0.0182(5) Uani d 1 . .
    H H18 0.2378 0.0755 0.4031 0.022 Uiso calc 1 . .
    C C19 0.14545(15) 0.07577(16) 0.48494(19) 0.0226(6) Uani d 1 . .
    H H19 0.1109 0.0648 0.4361 0.027 Uiso calc 1 . .
    C C20 0.12180(15) 0.08566(17) 0.5767(2) 0.0247(6) Uani d 1 . .
    C C21 0.17150(15) 0.09807(17) 0.64941(19) 0.0243(6) Uani d 1 . .
    H H21 0.1546 0.1021 0.7123 0.029 Uiso calc 1 . .
    C C22 0.24660(15) 0.10459(16) 0.62882(17) 0.0204(5) Uani d 1 . .
    H H22 0.2811 0.1135 0.6782 0.025 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br1 C20 . 1.901(3) ?
    O1 C5 . 1.239(3) ?
    O2 C14 . 1.211(3) ?
    O3 C14 . 1.354(3) ?
    O3 C15 . 1.454(3) ?
    N1 H1 . 0.89(3) ?
    N1 C2 . 1.391(3) ?
    N1 C9 . 1.362(3) ?
    C2 C3 . 1.351(3) ?
    C2 C13 . 1.505(3) ?
    C3 C4 . 1.528(3) ?
    C3 C14 . 1.471(3) ?
    C4 H4 . 1.0000 ?
    C4 C10 . 1.520(3) ?
    C4 C17 . 1.526(3) ?
    C5 C6 . 1.515(3) ?
    C5 C10 . 1.441(3) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C6 C7 . 1.530(3) ?
    C7 C8 . 1.533(3) ?
    C7 C11 . 1.532(3) ?
    C7 C12 . 1.533(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8 C9 . 1.497(3) ?
    C9 C10 . 1.357(3) ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15 C16 . 1.485(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.390(3) ?
    C17 C22 . 1.397(3) ?
    C18 H18 . 0.9500 ?
    C18 C19 . 1.392(4) ?
    C19 H19 . 0.9500 ?
    C19 C20 . 1.385(4) ?
    C20 C21 . 1.384(4) ?
    C21 H21 . 0.9500 ?
    C21 C22 . 1.390(4) ?
    C22 H22 . 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
    C14 O3 C15 . . 115.35(19) ?
    C2 N1 H1 . . 117.3(19) ?
    C9 N1 H1 . . 120.2(19) ?
    C9 N1 C2 . . 122.3(2) ?
    N1 C2 C13 . . 113.0(2) ?
    C3 C2 N1 . . 120.5(2) ?
    C3 C2 C13 . . 126.5(2) ?
    C2 C3 C4 . . 121.0(2) ?
    C2 C3 C14 . . 120.0(2) ?
    C14 C3 C4 . . 118.9(2) ?
    C3 C4 H4 . . 108.1 ?
    C10 C4 C3 . . 110.53(18) ?
    C10 C4 H4 . . 108.1 ?
    C10 C4 C17 . . 110.66(19) ?
    C17 C4 C3 . . 111.08(19) ?
    C17 C4 H4 . . 108.1 ?
    O1 C5 C6 . . 120.2(2) ?
    O1 C5 C10 . . 121.0(2) ?
    C10 C5 C6 . . 118.74(19) ?
    C5 C6 H6A . . 108.4 ?
    C5 C6 H6B . . 108.4 ?
    C5 C6 C7 . . 115.32(19) ?
    H6A C6 H6B . . 107.5 ?
    C7 C6 H6A . . 108.4 ?
    C7 C6 H6B . . 108.4 ?
    C6 C7 C8 . . 108.26(19) ?
    C6 C7 C11 . . 110.12(19) ?
    C6 C7 C12 . . 109.4(2) ?
    C11 C7 C8 . . 110.3(2) ?
    C11 C7 C12 . . 109.7(2) ?
    C12 C7 C8 . . 109.03(19) ?
    C7 C8 H8A . . 108.9 ?
    C7 C8 H8B . . 108.9 ?
    H8A C8 H8B . . 107.8 ?
    C9 C8 C7 . . 113.18(19) ?
    C9 C8 H8A . . 108.9 ?
    C9 C8 H8B . . 108.9 ?
    N1 C9 C8 . . 115.85(19) ?
    C10 C9 N1 . . 120.4(2) ?
    C10 C9 C8 . . 123.6(2) ?
    C5 C10 C4 . . 118.5(2) ?
    C9 C10 C4 . . 121.6(2) ?
    C9 C10 C5 . . 119.9(2) ?
    C7 C11 H11A . . 109.5 ?
    C7 C11 H11B . . 109.5 ?
    C7 C11 H11C . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 C12 H12A . . 109.5 ?
    C7 C12 H12B . . 109.5 ?
    C7 C12 H12C . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C2 C13 H13A . . 109.5 ?
    C2 C13 H13B . . 109.5 ?
    C2 C13 H13C . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O2 C14 O3 . . 122.2(2) ?
    O2 C14 C3 . . 126.7(2) ?
    O3 C14 C3 . . 111.2(2) ?
    O3 C15 H15A . . 110.1 ?
    O3 C15 H15B . . 110.1 ?
    O3 C15 C16 . . 107.9(2) ?
    H15A C15 H15B . . 108.4 ?
    C16 C15 H15A . . 110.1 ?
    C16 C15 H15B . . 110.1 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C18 C17 C4 . . 120.4(2) ?
    C18 C17 C22 . . 118.5(2) ?
    C22 C17 C4 . . 121.1(2) ?
    C17 C18 H18 . . 119.3 ?
    C17 C18 C19 . . 121.3(2) ?
    C19 C18 H18 . . 119.3 ?
    C18 C19 H19 . . 120.7 ?
    C20 C19 C18 . . 118.6(2) ?
    C20 C19 H19 . . 120.7 ?
    C19 C20 Br1 . . 118.8(2) ?
    C21 C20 Br1 . . 119.6(2) ?
    C21 C20 C19 . . 121.6(2) ?
    C20 C21 H21 . . 120.5 ?
    C20 C21 C22 . . 118.9(2) ?
    C22 C21 H21 . . 120.5 ?
    C17 C22 H22 . . 119.5 ?
    C21 C22 C17 . . 121.0(2) ?
    C21 C22 H22 . . 119.5 ?
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
    Br1 C20 C21 C22 . . . . -174.96(19) ?
    O1 C5 C6 C7 . . . . 159.3(2) ?
    O1 C5 C10 C4 . . . . -7.0(3) ?
    O1 C5 C10 C9 . . . . 173.0(2) ?
    N1 C2 C3 C4 . . . . -4.1(4) ?
    N1 C2 C3 C14 . . . . 178.3(2) ?
    N1 C9 C10 C4 . . . . 7.5(4) ?
    N1 C9 C10 C5 . . . . -172.4(2) ?
    C2 N1 C9 C8 . . . . -167.3(2) ?
    C2 N1 C9 C10 . . . . 8.7(4) ?
    C2 C3 C4 C10 . . . . 17.6(3) ?
    C2 C3 C4 C17 . . . . -105.7(3) ?
    C2 C3 C14 O2 . . . . 5.8(4) ?
    C2 C3 C14 O3 . . . . -174.8(2) ?
    C3 C4 C10 C5 . . . . 160.6(2) ?
    C3 C4 C10 C9 . . . . -19.4(3) ?
    C3 C4 C17 C18 . . . . 55.4(3) ?
    C3 C4 C17 C22 . . . . -124.6(2) ?
    C4 C3 C14 O2 . . . . -171.8(2) ?
    C4 C3 C14 O3 . . . . 7.6(3) ?
    C4 C17 C18 C19 . . . . -177.6(2) ?
    C4 C17 C22 C21 . . . . 177.8(2) ?
    C5 C6 C7 C8 . . . . 48.7(3) ?
    C5 C6 C7 C11 . . . . -72.0(3) ?
    C5 C6 C7 C12 . . . . 167.4(2) ?
    C6 C5 C10 C4 . . . . 176.1(2) ?
    C6 C5 C10 C9 . . . . -3.9(3) ?
    C6 C7 C8 C9 . . . . -48.5(3) ?
    C7 C8 C9 N1 . . . . -159.3(2) ?
    C7 C8 C9 C10 . . . . 24.9(3) ?
    C8 C9 C10 C4 . . . . -176.9(2) ?
    C8 C9 C10 C5 . . . . 3.2(4) ?
    C9 N1 C2 C3 . . . . -10.4(4) ?
    C9 N1 C2 C13 . . . . 168.4(2) ?
    C10 C4 C17 C18 . . . . -67.8(3) ?
    C10 C4 C17 C22 . . . . 112.2(2) ?
    C10 C5 C6 C7 . . . . -23.8(3) ?
    C11 C7 C8 C9 . . . . 72.0(2) ?
    C12 C7 C8 C9 . . . . -167.4(2) ?
    C13 C2 C3 C4 . . . . 177.2(3) ?
    C13 C2 C3 C14 . . . . -0.4(4) ?
    C14 O3 C15 C16 . . . . 170.6(3) ?
    C14 C3 C4 C10 . . . . -164.8(2) ?
    C14 C3 C4 C17 . . . . 72.0(3) ?
    C15 O3 C14 O2 . . . . -1.3(3) ?
    C15 O3 C14 C3 . . . . 179.3(2) ?
    C17 C4 C10 C5 . . . . -75.9(3) ?
    C17 C4 C10 C9 . . . . 104.1(2) ?
    C17 C18 C19 C20 . . . . 0.0(4) ?
    C18 C17 C22 C21 . . . . -2.2(4) ?
    C18 C19 C20 Br1 . . . . 175.19(19) ?
    C18 C19 C20 C21 . . . . -2.7(4) ?
    C19 C20 C21 C22 . . . . 2.9(4) ?
    C20 C21 C22 C17 . . . . -0.4(4) ?
    C22 C17 C18 C19 . . . . 2.4(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
    N1 H1 O1 8 0.89(3) 1.94(3) 2.812(2) 168(3)
_shelxl_version_number         .2013
data_II
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_database_code_depnum_ccdc_archive     'CCDC 1012126'
_chemical_name_systematic
;\
Ethyl
4-(3-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-\
carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 Br N O3'
_chemical_formula_sum     'C21 H24 Br N O3'
_chemical_formula_iupac     'C21 H24 Br N O3'
_chemical_formula_weight     418.32
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c n'
_space_group_name_Hall     '-P 2n 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     17.0813(5)
_cell_length_b     15.4877(5)
_cell_length_c     14.2544(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3771.0(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9015
_cell_measurement_theta_min     2.28
_cell_measurement_theta_max     29.05
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.399
_exptl_crystal_size_mid     0.209
_exptl_crystal_size_min     0.186
_exptl_crystal_density_diffrn     1.474
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1728
_exptl_absorpt_coefficient_mu     2.201
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.8390
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.01
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     55070
_diffrn_reflns_av_R_equivalents     0.0322
_diffrn_reflns_theta_min     1.775
_diffrn_reflns_theta_max     29.081
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_refine_special_details
;
;
_reflns_number_total     5055
_reflns_number_gt     4278
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0406
_refine_ls_R_factor_gt     0.0318
_refine_ls_wR_factor_gt     0.0797
_refine_ls_wR_factor_ref     0.0840
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     5055
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0428P)²+3.6244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.313
_refine_diff_density_min     -0.381
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.92434(2) 0.52663(2) 0.66172(2) 0.01998(7) Uani d 1 . .
    O O1 0.61002(8) 0.46449(8) 0.36349(9) 0.0170(3) Uani d 1 . .
    O O2 0.60547(9) 0.83120(9) 0.54611(11) 0.0273(3) Uani d 1 . .
    O O3 0.66301(8) 0.77388(8) 0.41978(10) 0.0235(3) Uani d 1 . .
    N N1 0.61112(9) 0.58166(9) 0.66708(10) 0.0132(3) Uani d 1 . .
    C C2 0.61780(9) 0.66563(11) 0.63433(12) 0.0132(3) Uani d 1 . .
    C C3 0.63546(9) 0.67997(11) 0.54285(12) 0.0132(3) Uani d 1 . .
    C C4 0.65961(9) 0.60546(10) 0.47927(11) 0.0117(3) Uani d 1 . .
    H H4 0.6397 0.6174 0.4146 0.014 Uiso calc 1 . .
    C C10 0.62185(9) 0.52300(10) 0.51443(11) 0.0105(3) Uani d 1 . .
    C C9 0.60504(9) 0.51293(10) 0.60705(11) 0.0105(3) Uani d 1 . .
    C C8 0.57528(9) 0.43036(11) 0.64894(11) 0.0126(3) Uani d 1 . .
    H H8A 0.5176 0.4335 0.6542 0.015 Uiso calc 1 . .
    H H8B 0.5968 0.4240 0.7130 0.015 Uiso calc 1 . .
    C C7 0.59747(10) 0.35080(10) 0.59090(12) 0.0129(3) Uani d 1 . .
    C C6 0.57615(10) 0.36838(11) 0.48787(12) 0.0143(3) Uani d 1 . .
    H H6A 0.5981 0.3214 0.4489 0.017 Uiso calc 1 . .
    H H6B 0.5185 0.3662 0.4816 0.017 Uiso calc 1 . .
    C C5 0.60455(9) 0.45362(11) 0.44924(11) 0.0112(3) Uani d 1 . .
    C C11 0.68524(11) 0.33164(12) 0.59932(14) 0.0208(4) Uani d 1 . .
    H H11A 0.6988 0.3228 0.6654 0.031 Uiso calc 1 . .
    H H11B 0.7152 0.3804 0.5743 0.031 Uiso calc 1 . .
    H H11C 0.6978 0.2794 0.5636 0.031 Uiso calc 1 . .
    C C12 0.55061(12) 0.27318(12) 0.62687(14) 0.0217(4) Uani d 1 . .
    H H12A 0.4946 0.2868 0.6252 0.033 Uiso calc 1 . .
    H H12B 0.5663 0.2602 0.6915 0.033 Uiso calc 1 . .
    H H12C 0.5610 0.2230 0.5869 0.033 Uiso calc 1 . .
    C C13 0.60140(11) 0.73340(12) 0.70714(13) 0.0193(4) Uani d 1 . .
    H H13A 0.5964 0.7060 0.7688 0.029 Uiso calc 1 . .
    H H13B 0.5525 0.7633 0.6916 0.029 Uiso calc 1 . .
    H H13C 0.6446 0.7751 0.7085 0.029 Uiso calc 1 . .
    C C14 0.63211(10) 0.76888(11) 0.50625(13) 0.0172(3) Uani d 1 . .
    C C15 0.66536(13) 0.86167(13) 0.38140(16) 0.0281(4) Uani d 1 . .
    H H15A 0.6813 0.9033 0.4305 0.034 Uiso calc 1 . .
    H H15B 0.6131 0.8785 0.3577 0.034 Uiso calc 1 . .
    C C16 0.72312(12) 0.86129(14) 0.30382(16) 0.0285(4) Uani d 1 . .
    H H16A 0.7739 0.8415 0.3275 0.043 Uiso calc 1 . .
    H H16B 0.7285 0.9198 0.2785 0.043 Uiso calc 1 . .
    H H16C 0.7052 0.8223 0.2541 0.043 Uiso calc 1 . .
    C C17 0.74878(10) 0.59554(10) 0.47466(11) 0.0124(3) Uani d 1 . .
    C C18 0.78958(9) 0.56824(11) 0.55396(11) 0.0130(3) Uani d 1 . .
    H H18 0.7620 0.5547 0.6099 0.016 Uiso calc 1 . .
    C C19 0.87044(10) 0.56085(11) 0.55114(12) 0.0137(3) Uani d 1 . .
    C C20 0.91306(10) 0.57960(11) 0.47084(13) 0.0161(3) Uani d 1 . .
    H H20 0.9685 0.5752 0.4702 0.019 Uiso calc 1 . .
    C C21 0.87189(11) 0.60498(12) 0.39144(13) 0.0199(4) Uani d 1 . .
    H H21 0.8996 0.6168 0.3351 0.024 Uiso calc 1 . .
    C C22 0.79094(10) 0.61342(12) 0.39305(12) 0.0177(3) Uani d 1 . .
    H H22 0.7640 0.6315 0.3381 0.021 Uiso calc 1 . .
    H H1 0.6037(14) 0.5739(15) 0.7262(18) 0.021(6) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br1 C19 . 1.9009(17) ?
    O1 C5 . 1.237(2) ?
    O2 C14 . 1.209(2) ?
    O3 C14 . 1.343(2) ?
    O3 C15 . 1.466(2) ?
    N1 C2 . 1.386(2) ?
    N1 C9 . 1.370(2) ?
    N1 H1 . 0.86(2) ?
    C2 C3 . 1.357(2) ?
    C2 C13 . 1.502(2) ?
    C3 C4 . 1.524(2) ?
    C3 C14 . 1.474(2) ?
    C4 H4 . 1.0000 ?
    C4 C10 . 1.516(2) ?
    C4 C17 . 1.532(2) ?
    C10 C9 . 1.360(2) ?
    C10 C5 . 1.451(2) ?
    C9 C8 . 1.500(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8 C7 . 1.532(2) ?
    C7 C6 . 1.537(2) ?
    C7 C11 . 1.533(2) ?
    C7 C12 . 1.533(2) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C6 C5 . 1.510(2) ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15 C16 . 1.482(3) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.394(2) ?
    C17 C22 . 1.396(2) ?
    C18 H18 . 0.9500 ?
    C18 C19 . 1.386(2) ?
    C19 C20 . 1.387(2) ?
    C20 H20 . 0.9500 ?
    C20 C21 . 1.389(3) ?
    C21 H21 . 0.9500 ?
    C21 C22 . 1.389(3) ?
    C22 H22 . 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
    C14 O3 C15 . . 113.99(15) ?
    C2 N1 H1 . . 118.2(16) ?
    C9 N1 C2 . . 121.67(14) ?
    C9 N1 H1 . . 119.5(16) ?
    N1 C2 C13 . . 114.04(15) ?
    C3 C2 N1 . . 119.69(15) ?
    C3 C2 C13 . . 126.23(16) ?
    C2 C3 C4 . . 120.52(15) ?
    C2 C3 C14 . . 118.99(16) ?
    C14 C3 C4 . . 120.49(15) ?
    C3 C4 H4 . . 108.4 ?
    C3 C4 C17 . . 111.75(13) ?
    C10 C4 C3 . . 109.02(13) ?
    C10 C4 H4 . . 108.4 ?
    C10 C4 C17 . . 110.65(13) ?
    C17 C4 H4 . . 108.4 ?
    C9 C10 C4 . . 120.49(14) ?
    C9 C10 C5 . . 119.58(14) ?
    C5 C10 C4 . . 119.92(14) ?
    N1 C9 C8 . . 116.08(14) ?
    C10 C9 N1 . . 120.08(15) ?
    C10 C9 C8 . . 123.76(15) ?
    C9 C8 H8A . . 109.0 ?
    C9 C8 H8B . . 109.0 ?
    C9 C8 C7 . . 112.76(13) ?
    H8A C8 H8B . . 107.8 ?
    C7 C8 H8A . . 109.0 ?
    C7 C8 H8B . . 109.0 ?
    C8 C7 C6 . . 108.35(13) ?
    C8 C7 C11 . . 110.82(14) ?
    C8 C7 C12 . . 108.72(14) ?
    C11 C7 C6 . . 109.92(14) ?
    C12 C7 C6 . . 109.56(14) ?
    C12 C7 C11 . . 109.43(14) ?
    C7 C6 H6A . . 108.5 ?
    C7 C6 H6B . . 108.5 ?
    H6A C6 H6B . . 107.5 ?
    C5 C6 C7 . . 115.28(14) ?
    C5 C6 H6A . . 108.5 ?
    C5 C6 H6B . . 108.5 ?
    O1 C5 C10 . . 121.10(15) ?
    O1 C5 C6 . . 120.22(15) ?
    C10 C5 C6 . . 118.63(14) ?
    C7 C11 H11A . . 109.5 ?
    C7 C11 H11B . . 109.5 ?
    C7 C11 H11C . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 C12 H12A . . 109.5 ?
    C7 C12 H12B . . 109.5 ?
    C7 C12 H12C . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C2 C13 H13A . . 109.5 ?
    C2 C13 H13B . . 109.5 ?
    C2 C13 H13C . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O2 C14 O3 . . 122.23(16) ?
    O2 C14 C3 . . 126.45(17) ?
    O3 C14 C3 . . 111.32(15) ?
    O3 C15 H15A . . 110.3 ?
    O3 C15 H15B . . 110.3 ?
    O3 C15 C16 . . 107.04(16) ?
    H15A C15 H15B . . 108.6 ?
    C16 C15 H15A . . 110.3 ?
    C16 C15 H15B . . 110.3 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C18 C17 C4 . . 119.53(14) ?
    C18 C17 C22 . . 118.56(15) ?
    C22 C17 C4 . . 121.91(15) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 C17 . . 119.98(15) ?
    C19 C18 H18 . . 120.0 ?
    C18 C19 Br1 . . 118.78(13) ?
    C18 C19 C20 . . 121.97(16) ?
    C20 C19 Br1 . . 119.24(13) ?
    C19 C20 H20 . . 121.1 ?
    C19 C20 C21 . . 117.76(16) ?
    C21 C20 H20 . . 121.1 ?
    C20 C21 H21 . . 119.4 ?
    C22 C21 C20 . . 121.13(16) ?
    C22 C21 H21 . . 119.4 ?
    C17 C22 H22 . . 119.7 ?
    C21 C22 C17 . . 120.58(17) ?
    C21 C22 H22 . . 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
    Br1 C19 C20 C21 . . . . -179.58(13) ?
    N1 C2 C3 C4 . . . . -8.9(2) ?
    N1 C2 C3 C14 . . . . 171.99(15) ?
    N1 C9 C8 C7 . . . . -159.09(14) ?
    C2 N1 C9 C10 . . . . 13.9(2) ?
    C2 N1 C9 C8 . . . . -162.93(14) ?
    C2 C3 C4 C10 . . . . 28.5(2) ?
    C2 C3 C4 C17 . . . . -94.13(18) ?
    C2 C3 C14 O2 . . . . -10.1(3) ?
    C2 C3 C14 O3 . . . . 170.08(15) ?
    C3 C4 C10 C9 . . . . -28.9(2) ?
    C3 C4 C10 C5 . . . . 152.04(14) ?
    C3 C4 C17 C18 . . . . 68.23(19) ?
    C3 C4 C17 C22 . . . . -111.52(18) ?
    C4 C3 C14 O2 . . . . 170.86(17) ?
    C4 C3 C14 O3 . . . . -9.0(2) ?
    C4 C10 C9 N1 . . . . 9.8(2) ?
    C4 C10 C9 C8 . . . . -173.61(14) ?
    C4 C10 C5 O1 . . . . -10.0(2) ?
    C4 C10 C5 C6 . . . . 172.64(14) ?
    C4 C17 C18 C19 . . . . -178.60(15) ?
    C4 C17 C22 C21 . . . . 179.09(16) ?
    C10 C4 C17 C18 . . . . -53.5(2) ?
    C10 C4 C17 C22 . . . . 126.79(17) ?
    C10 C9 C8 C7 . . . . 24.2(2) ?
    C9 N1 C2 C3 . . . . -14.3(2) ?
    C9 N1 C2 C13 . . . . 163.81(15) ?
    C9 C10 C5 O1 . . . . 170.98(16) ?
    C9 C10 C5 C6 . . . . -6.4(2) ?
    C9 C8 C7 C6 . . . . -49.12(18) ?
    C9 C8 C7 C11 . . . . 71.56(18) ?
    C9 C8 C7 C12 . . . . -168.13(14) ?
    C8 C7 C6 C5 . . . . 49.17(18) ?
    C7 C6 C5 O1 . . . . 160.14(15) ?
    C7 C6 C5 C10 . . . . -22.5(2) ?
    C5 C10 C9 N1 . . . . -171.17(14) ?
    C5 C10 C9 C8 . . . . 5.4(2) ?
    C11 C7 C6 C5 . . . . -72.07(18) ?
    C12 C7 C6 C5 . . . . 167.65(14) ?
    C13 C2 C3 C4 . . . . 173.19(16) ?
    C13 C2 C3 C14 . . . . -5.9(3) ?
    C14 O3 C15 C16 . . . . 161.23(17) ?
    C14 C3 C4 C10 . . . . -152.46(14) ?
    C14 C3 C4 C17 . . . . 84.92(18) ?
    C15 O3 C14 O2 . . . . 3.3(3) ?
    C15 O3 C14 C3 . . . . -176.83(15) ?
    C17 C4 C10 C9 . . . . 94.34(18) ?
    C17 C4 C10 C5 . . . . -84.68(17) ?
    C17 C18 C19 Br1 . . . . 178.21(12) ?
    C17 C18 C19 C20 . . . . -0.3(3) ?
    C18 C17 C22 C21 . . . . -0.7(3) ?
    C18 C19 C20 C21 . . . . -1.1(3) ?
    C19 C20 C21 C22 . . . . 1.6(3) ?
    C20 C21 C22 C17 . . . . -0.7(3) ?
    C22 C17 C18 C19 . . . . 1.1(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
    N1 H1 O1 8_566 0.86(2) 2.05(2) 2.8896(19) 166(2)
_shelxl_version_number         .2013
data_III
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_database_code_depnum_ccdc_archive     'CCDC 1012127'
_chemical_name_systematic
;\
Ethyl
4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-\
carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 Br N O3'
_chemical_formula_sum     'C21 H24 Br N O3'
_chemical_formula_iupac     'C21 H24 Br N O3'
_chemical_formula_weight     418.32
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.5012(18)
_cell_length_b     18.299(2)
_cell_length_c     15.1952(19)
_cell_angle_alpha     90
_cell_angle_beta     107.5262(15)
_cell_angle_gamma     90
_cell_volume     3844.9(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9934
_cell_measurement_theta_min     2.226
_cell_measurement_theta_max     27.659
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'translucent yellow'
_exptl_crystal_size_max     0.337
_exptl_crystal_size_mid     0.163
_exptl_crystal_size_min     0.075
_exptl_crystal_density_diffrn     1.445
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1728
_exptl_absorpt_coefficient_mu     2.158
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.8663
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.4
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     45465
_diffrn_reflns_av_R_equivalents     0.0651
_diffrn_reflns_theta_min     1.473
_diffrn_reflns_theta_max     27.662
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_refine_special_details
;
;
_reflns_number_total     8935
_reflns_number_gt     6859
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0582
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.0738
_refine_ls_wR_factor_ref     0.0811
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     8935
_refine_ls_number_parameters     485
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0324P)²+2.2792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.459
_refine_diff_density_min     -0.469
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1A 0.39565(2) 0.30789(2) 0.25454(2) 0.01430(7) Uani d 1 . .
    O O1A 0.28043(11) 0.45760(9) 0.12019(11) 0.0122(4) Uani d 1 . .
    O O2A 0.04711(13) 0.20468(10) 0.24987(15) 0.0262(5) Uani d 1 . .
    O O3A 0.20232(12) 0.23877(9) 0.29061(12) 0.0148(4) Uani d 1 . .
    N N1A -0.01715(15) 0.42917(11) 0.17929(14) 0.0110(4) Uani d 1 . .
    C C2A 0.00080(17) 0.35786(13) 0.21030(16) 0.0117(5) Uani d 1 . .
    C C3A 0.08940(16) 0.32797(13) 0.22333(16) 0.0100(5) Uani d 1 . .
    C C4A 0.17328(16) 0.37166(13) 0.20857(16) 0.0096(5) Uani d 1 . .
    H H4A 0.2055 0.3416 0.1714 0.012 Uiso calc 1 . .
    C C10A 0.13654(16) 0.44210(13) 0.15653(16) 0.0094(5) Uani d 1 . .
    C C9A 0.04751(17) 0.46991(13) 0.15143(16) 0.0099(5) Uani d 1 . .
    C C8A 0.01507(17) 0.54547(13) 0.11637(17) 0.0113(5) Uani d 1 . .
    H H8AA -0.0255 0.5659 0.1524 0.014 Uiso calc 1 . .
    H H8AB -0.0254 0.5422 0.0511 0.014 Uiso calc 1 . .
    C C7A 0.10023(17) 0.59772(13) 0.12310(17) 0.0114(5) Uani d 1 . .
    C C6A 0.17181(17) 0.55891(13) 0.08212(16) 0.0111(5) Uani d 1 . .
    H H6AA 0.1422 0.5549 0.0145 0.013 Uiso calc 1 . .
    H H6AB 0.2305 0.5895 0.0934 0.013 Uiso calc 1 . .
    C C5A 0.20149(17) 0.48342(13) 0.12076(16) 0.0104(5) Uani d 1 . .
    C C11A 0.15088(18) 0.61815(14) 0.22402(17) 0.0160(5) Uani d 1 . .
    H H11A 0.1035 0.6387 0.2515 0.024 Uiso calc 1 . .
    H H11B 0.2014 0.6544 0.2267 0.024 Uiso calc 1 . .
    H H11C 0.1801 0.5744 0.2584 0.024 Uiso calc 1 . .
    C C12A 0.06180(18) 0.66689(14) 0.06839(18) 0.0168(6) Uani d 1 . .
    H H12A 0.0299 0.6541 0.0037 0.025 Uiso calc 1 . .
    H H12B 0.1156 0.7003 0.0720 0.025 Uiso calc 1 . .
    H H12C 0.0152 0.6907 0.0942 0.025 Uiso calc 1 . .
    C C13A -0.08558(18) 0.32166(14) 0.22696(19) 0.0171(6) Uani d 1 . .
    H H13A -0.1282 0.3590 0.2398 0.026 Uiso calc 1 . .
    H H13B -0.0639 0.2885 0.2799 0.026 Uiso calc 1 . .
    H H13C -0.1209 0.2938 0.1720 0.026 Uiso calc 1 . .
    C C14A 0.10710(17) 0.25154(14) 0.25480(17) 0.0133(5) Uani d 1 . .
    C C15A 0.23069(18) 0.16497(13) 0.32241(18) 0.0155(5) Uani d 1 . .
    H H15A 0.2953 0.1544 0.3160 0.019 Uiso calc 1 . .
    H H15B 0.1841 0.1298 0.2833 0.019 Uiso calc 1 . .
    C C16A 0.2338(2) 0.15485(15) 0.42185(18) 0.0205(6) Uani d 1 . .
    H H16A 0.1693 0.1633 0.4279 0.031 Uiso calc 1 . .
    H H16B 0.2796 0.1898 0.4607 0.031 Uiso calc 1 . .
    H H16C 0.2547 0.1049 0.4415 0.031 Uiso calc 1 . .
    C C17A 0.24881(17) 0.39335(13) 0.29969(16) 0.0099(5) Uani d 1 . .
    C C18A 0.34612(17) 0.37375(14) 0.32615(16) 0.0129(5) Uani d 1 . .
    C C19A 0.41183(18) 0.40080(14) 0.40664(17) 0.0155(5) Uani d 1 . .
    H H19A 0.4777 0.3862 0.4236 0.019 Uiso calc 1 . .
    C C20A 0.38027(19) 0.44895(15) 0.46146(17) 0.0181(6) Uani d 1 . .
    H H20A 0.4250 0.4683 0.5156 0.022 Uiso calc 1 . .
    C C21A 0.28354(19) 0.46919(14) 0.43783(17) 0.0167(6) Uani d 1 . .
    H H21A 0.2619 0.5022 0.4757 0.020 Uiso calc 1 . .
    C C22A 0.21920(18) 0.44091(13) 0.35874(17) 0.0142(5) Uani d 1 . .
    H H22A 0.1529 0.4540 0.3437 0.017 Uiso calc 1 . .
    Br Br1B 0.08223(2) 0.00989(2) 0.13780(2) 0.01685(7) Uani d 1 . .
    O O1B 0.21907(11) -0.03473(9) 0.35984(12) 0.0139(4) Uani d 1 . .
    O O2B 0.41353(12) 0.16979(9) 0.13408(12) 0.0158(4) Uani d 1 . .
    O O3B 0.26479(11) 0.12336(9) 0.11364(11) 0.0130(4) Uani d 1 . .
    N N1B 0.51999(15) -0.01424(12) 0.30637(14) 0.0116(4) Uani d 1 . .
    C C2B 0.48978(17) 0.04219(13) 0.24329(16) 0.0104(5) Uani d 1 . .
    C C3B 0.39436(17) 0.05815(13) 0.21022(16) 0.0094(5) Uani d 1 . .
    C C4B 0.31871(16) 0.01002(13) 0.23282(16) 0.0090(5) Uani d 1 . .
    H H4B 0.2658 0.0421 0.2405 0.011 Uiso calc 1 . .
    C C10B 0.36467(16) -0.02951(13) 0.32331(16) 0.0090(5) Uani d 1 . .
    C C9B 0.46114(17) -0.04440(13) 0.35161(16) 0.0096(5) Uani d 1 . .
    C C8B 0.50953(17) -0.09235(13) 0.43263(16) 0.0114(5) Uani d 1 . .
    H H8BA 0.5407 -0.0612 0.4867 0.014 Uiso calc 1 . .
    H H8BB 0.5607 -0.1214 0.4182 0.014 Uiso calc 1 . .
    C C7B 0.43782(17) -0.14455(13) 0.45732(16) 0.0117(5) Uani d 1 . .
    C C6B 0.35073(17) -0.09960(13) 0.46295(16) 0.0109(5) Uani d 1 . .
    H H6BA 0.3012 -0.1333 0.4724 0.013 Uiso calc 1 . .
    H H6BB 0.3715 -0.0673 0.5176 0.013 Uiso calc 1 . .
    C C5B 0.30492(17) -0.05315(13) 0.37865(16) 0.0110(5) Uani d 1 . .
    C C12B 0.48777(19) -0.17893(15) 0.55204(18) 0.0182(6) Uani d 1 . .
    H H12D 0.5411 -0.2101 0.5476 0.027 Uiso calc 1 . .
    H H12E 0.4409 -0.2084 0.5715 0.027 Uiso calc 1 . .
    H H12F 0.5131 -0.1402 0.5974 0.027 Uiso calc 1 . .
    C C11B 0.40569(19) -0.20507(14) 0.38480(18) 0.0165(6) Uani d 1 . .
    H H11D 0.3742 -0.1832 0.3243 0.025 Uiso calc 1 . .
    H H11E 0.3601 -0.2376 0.4017 0.025 Uiso calc 1 . .
    H H11F 0.4623 -0.2332 0.3820 0.025 Uiso calc 1 . .
    C C13B 0.57203(17) 0.07931(14) 0.22026(18) 0.0155(5) Uani d 1 . .
    H H13D 0.5937 0.1214 0.2611 0.023 Uiso calc 1 . .
    H H13E 0.5504 0.0959 0.1559 0.023 Uiso calc 1 . .
    H H13F 0.6257 0.0448 0.2287 0.023 Uiso calc 1 . .
    C C14B 0.36205(17) 0.12248(13) 0.15021(16) 0.0112(5) Uani d 1 . .
    C C15B 0.22766(18) 0.18339(14) 0.05020(18) 0.0164(6) Uani d 1 . .
    H H15C 0.2565 0.1822 -0.0011 0.020 Uiso calc 1 . .
    H H15D 0.2440 0.2307 0.0827 0.020 Uiso calc 1 . .
    C C16B 0.11964(19) 0.17455(16) 0.0134(2) 0.0240(6) Uani d 1 . .
    H H16D 0.0924 0.2141 -0.0301 0.036 Uiso calc 1 . .
    H H16E 0.0918 0.1763 0.0647 0.036 Uiso calc 1 . .
    H H16F 0.1043 0.1274 -0.0183 0.036 Uiso calc 1 . .
    C C17B 0.27431(17) -0.04582(13) 0.15652(16) 0.0107(5) Uani d 1 . .
    C C18B 0.17577(17) -0.05192(14) 0.10999(17) 0.0128(5) Uani d 1 . .
    C C19B 0.13963(19) -0.10322(15) 0.04075(18) 0.0196(6) Uani d 1 . .
    H H19B 0.0721 -0.1060 0.0103 0.023 Uiso calc 1 . .
    C C20B 0.2024(2) -0.15016(15) 0.01647(19) 0.0233(6) Uani d 1 . .
    H H20B 0.1784 -0.1847 -0.0317 0.028 Uiso calc 1 . .
    C C21B 0.3010(2) -0.14683(15) 0.06268(18) 0.0200(6) Uani d 1 . .
    H H21B 0.3444 -0.1797 0.0471 0.024 Uiso calc 1 . .
    C C22B 0.33544(18) -0.09546(13) 0.13130(17) 0.0136(5) Uani d 1 . .
    H H22B 0.4029 -0.0937 0.1625 0.016 Uiso calc 1 . .
    H H1B 0.576(2) -0.0236(14) 0.3237(18) 0.011(7) Uiso d 1 . .
    H H1A -0.0714(19) 0.4467(14) 0.1738(17) 0.006(7) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br1A C18A . 1.904(2) ?
    O1A C5A . 1.241(3) ?
    O2A C14A . 1.208(3) ?
    O3A C14A . 1.343(3) ?
    O3A C15A . 1.451(3) ?
    N1A C2A . 1.385(3) ?
    N1A C9A . 1.361(3) ?
    N1A H1A . 0.83(3) ?
    C2A C3A . 1.355(3) ?
    C2A C13A . 1.504(3) ?
    C3A C4A . 1.528(3) ?
    C3A C14A . 1.475(3) ?
    C4A H4A . 1.0000 ?
    C4A C10A . 1.522(3) ?
    C4A C17A . 1.537(3) ?
    C10A C9A . 1.368(3) ?
    C10A C5A . 1.436(3) ?
    C9A C8A . 1.505(3) ?
    C8A H8AA . 0.9900 ?
    C8A H8AB . 0.9900 ?
    C8A C7A . 1.541(3) ?
    C7A C6A . 1.536(3) ?
    C7A C11A . 1.534(3) ?
    C7A C12A . 1.525(3) ?
    C6A H6AA . 0.9900 ?
    C6A H6AB . 0.9900 ?
    C6A C5A . 1.512(3) ?
    C11A H11A . 0.9800 ?
    C11A H11B . 0.9800 ?
    C11A H11C . 0.9800 ?
    C12A H12A . 0.9800 ?
    C12A H12B . 0.9800 ?
    C12A H12C . 0.9800 ?
    C13A H13A . 0.9800 ?
    C13A H13B . 0.9800 ?
    C13A H13C . 0.9800 ?
    C15A H15A . 0.9900 ?
    C15A H15B . 0.9900 ?
    C15A C16A . 1.509(4) ?
    C16A H16A . 0.9800 ?
    C16A H16B . 0.9800 ?
    C16A H16C . 0.9800 ?
    C17A C18A . 1.393(3) ?
    C17A C22A . 1.407(3) ?
    C18A C19A . 1.395(3) ?
    C19A H19A . 0.9500 ?
    C19A C20A . 1.382(4) ?
    C20A H20A . 0.9500 ?
    C20A C21A . 1.389(4) ?
    C21A H21A . 0.9500 ?
    C21A C22A . 1.381(3) ?
    C22A H22A . 0.9500 ?
    Br1B C18B . 1.909(2) ?
    O1B C5B . 1.237(3) ?
    O2B C14B . 1.215(3) ?
    O3B C14B . 1.351(3) ?
    O3B C15B . 1.454(3) ?
    N1B C2B . 1.387(3) ?
    N1B C9B . 1.363(3) ?
    N1B H1B . 0.80(3) ?
    C2B C3B . 1.354(3) ?
    C2B C13B . 1.503(3) ?
    C3B C4B . 1.524(3) ?
    C3B C14B . 1.476(3) ?
    C4B H4B . 1.0000 ?
    C4B C10B . 1.519(3) ?
    C4B C17B . 1.534(3) ?
    C10B C9B . 1.362(3) ?
    C10B C5B . 1.443(3) ?
    C9B C8B . 1.503(3) ?
    C8B H8BA . 0.9900 ?
    C8B H8BB . 0.9900 ?
    C8B C7B . 1.539(3) ?
    C7B C6B . 1.531(3) ?
    C7B C12B . 1.538(3) ?
    C7B C11B . 1.532(3) ?
    C6B H6BA . 0.9900 ?
    C6B H6BB . 0.9900 ?
    C6B C5B . 1.514(3) ?
    C12B H12D . 0.9800 ?
    C12B H12E . 0.9800 ?
    C12B H12F . 0.9800 ?
    C11B H11D . 0.9800 ?
    C11B H11E . 0.9800 ?
    C11B H11F . 0.9800 ?
    C13B H13D . 0.9800 ?
    C13B H13E . 0.9800 ?
    C13B H13F . 0.9800 ?
    C15B H15C . 0.9900 ?
    C15B H15D . 0.9900 ?
    C15B C16B . 1.505(4) ?
    C16B H16D . 0.9800 ?
    C16B H16E . 0.9800 ?
    C16B H16F . 0.9800 ?
    C17B C18B . 1.395(3) ?
    C17B C22B . 1.401(3) ?
    C18B C19B . 1.390(4) ?
    C19B H19B . 0.9500 ?
    C19B C20B . 1.381(4) ?
    C20B H20B . 0.9500 ?
    C20B C21B . 1.391(4) ?
    C21B H21B . 0.9500 ?
    C21B C22B . 1.381(4) ?
    C22B H22B . 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
    C14A O3A C15A . . 116.77(19) ?
    C2A N1A H1A . . 118.2(17) ?
    C9A N1A C2A . . 123.0(2) ?
    C9A N1A H1A . . 118.6(17) ?
    N1A C2A C13A . . 113.0(2) ?
    C3A C2A N1A . . 120.2(2) ?
    C3A C2A C13A . . 126.8(2) ?
    C2A C3A C4A . . 121.9(2) ?
    C2A C3A C14A . . 119.7(2) ?
    C14A C3A C4A . . 118.4(2) ?
    C3A C4A H4A . . 108.9 ?
    C3A C4A C17A . . 112.70(19) ?
    C10A C4A C3A . . 110.48(19) ?
    C10A C4A H4A . . 108.9 ?
    C10A C4A C17A . . 107.00(19) ?
    C17A C4A H4A . . 108.9 ?
    C9A C10A C4A . . 121.4(2) ?
    C9A C10A C5A . . 119.9(2) ?
    C5A C10A C4A . . 118.4(2) ?
    N1A C9A C10A . . 120.4(2) ?
    N1A C9A C8A . . 116.2(2) ?
    C10A C9A C8A . . 123.4(2) ?
    C9A C8A H8AA . . 109.0 ?
    C9A C8A H8AB . . 109.0 ?
    C9A C8A C7A . . 112.81(19) ?
    H8AA C8A H8AB . . 107.8 ?
    C7A C8A H8AA . . 109.0 ?
    C7A C8A H8AB . . 109.0 ?
    C6A C7A C8A . . 108.19(19) ?
    C11A C7A C8A . . 110.5(2) ?
    C11A C7A C6A . . 109.8(2) ?
    C12A C7A C8A . . 108.96(19) ?
    C12A C7A C6A . . 110.1(2) ?
    C12A C7A C11A . . 109.2(2) ?
    C7A C6A H6AA . . 108.7 ?
    C7A C6A H6AB . . 108.7 ?
    H6AA C6A H6AB . . 107.6 ?
    C5A C6A C7A . . 114.4(2) ?
    C5A C6A H6AA . . 108.7 ?
    C5A C6A H6AB . . 108.7 ?
    O1A C5A C10A . . 120.9(2) ?
    O1A C5A C6A . . 120.0(2) ?
    C10A C5A C6A . . 119.1(2) ?
    C7A C11A H11A . . 109.5 ?
    C7A C11A H11B . . 109.5 ?
    C7A C11A H11C . . 109.5 ?
    H11A C11A H11B . . 109.5 ?
    H11A C11A H11C . . 109.5 ?
    H11B C11A H11C . . 109.5 ?
    C7A C12A H12A . . 109.5 ?
    C7A C12A H12B . . 109.5 ?
    C7A C12A H12C . . 109.5 ?
    H12A C12A H12B . . 109.5 ?
    H12A C12A H12C . . 109.5 ?
    H12B C12A H12C . . 109.5 ?
    C2A C13A H13A . . 109.5 ?
    C2A C13A H13B . . 109.5 ?
    C2A C13A H13C . . 109.5 ?
    H13A C13A H13B . . 109.5 ?
    H13A C13A H13C . . 109.5 ?
    H13B C13A H13C . . 109.5 ?
    O2A C14A O3A . . 122.3(2) ?
    O2A C14A C3A . . 127.0(2) ?
    O3A C14A C3A . . 110.7(2) ?
    O3A C15A H15A . . 109.3 ?
    O3A C15A H15B . . 109.3 ?
    O3A C15A C16A . . 111.6(2) ?
    H15A C15A H15B . . 108.0 ?
    C16A C15A H15A . . 109.3 ?
    C16A C15A H15B . . 109.3 ?
    C15A C16A H16A . . 109.5 ?
    C15A C16A H16B . . 109.5 ?
    C15A C16A H16C . . 109.5 ?
    H16A C16A H16B . . 109.5 ?
    H16A C16A H16C . . 109.5 ?
    H16B C16A H16C . . 109.5 ?
    C18A C17A C4A . . 125.4(2) ?
    C18A C17A C22A . . 116.9(2) ?
    C22A C17A C4A . . 117.6(2) ?
    C17A C18A Br1A . . 121.46(18) ?
    C17A C18A C19A . . 121.8(2) ?
    C19A C18A Br1A . . 116.74(18) ?
    C18A C19A H19A . . 120.3 ?
    C20A C19A C18A . . 119.5(2) ?
    C20A C19A H19A . . 120.3 ?
    C19A C20A H20A . . 119.8 ?
    C19A C20A C21A . . 120.4(2) ?
    C21A C20A H20A . . 119.8 ?
    C20A C21A H21A . . 120.3 ?
    C22A C21A C20A . . 119.3(2) ?
    C22A C21A H21A . . 120.3 ?
    C17A C22A H22A . . 119.0 ?
    C21A C22A C17A . . 122.1(2) ?
    C21A C22A H22A . . 119.0 ?
    C14B O3B C15B . . 114.45(19) ?
    C2B N1B H1B . . 117.8(19) ?
    C9B N1B C2B . . 122.3(2) ?
    C9B N1B H1B . . 118.8(19) ?
    N1B C2B C13B . . 112.9(2) ?
    C3B C2B N1B . . 119.5(2) ?
    C3B C2B C13B . . 127.6(2) ?
    C2B C3B C4B . . 121.1(2) ?
    C2B C3B C14B . . 120.0(2) ?
    C14B C3B C4B . . 118.9(2) ?
    C3B C4B H4B . . 108.5 ?
    C3B C4B C17B . . 112.42(19) ?
    C10B C4B C3B . . 109.25(19) ?
    C10B C4B H4B . . 108.5 ?
    C10B C4B C17B . . 109.69(19) ?
    C17B C4B H4B . . 108.5 ?
    C9B C10B C4B . . 120.7(2) ?
    C9B C10B C5B . . 119.7(2) ?
    C5B C10B C4B . . 119.6(2) ?
    N1B C9B C8B . . 116.2(2) ?
    C10B C9B N1B . . 120.0(2) ?
    C10B C9B C8B . . 123.9(2) ?
    C9B C8B H8BA . . 109.1 ?
    C9B C8B H8BB . . 109.1 ?
    C9B C8B C7B . . 112.27(19) ?
    H8BA C8B H8BB . . 107.9 ?
    C7B C8B H8BA . . 109.1 ?
    C7B C8B H8BB . . 109.1 ?
    C6B C7B C8B . . 108.03(19) ?
    C6B C7B C12B . . 109.36(19) ?
    C6B C7B C11B . . 110.6(2) ?
    C12B C7B C8B . . 108.64(19) ?
    C11B C7B C8B . . 110.8(2) ?
    C11B C7B C12B . . 109.4(2) ?
    C7B C6B H6BA . . 108.7 ?
    C7B C6B H6BB . . 108.7 ?
    H6BA C6B H6BB . . 107.6 ?
    C5B C6B C7B . . 114.42(19) ?
    C5B C6B H6BA . . 108.7 ?
    C5B C6B H6BB . . 108.7 ?
    O1B C5B C10B . . 121.5(2) ?
    O1B C5B C6B . . 120.2(2) ?
    C10B C5B C6B . . 118.3(2) ?
    C7B C12B H12D . . 109.5 ?
    C7B C12B H12E . . 109.5 ?
    C7B C12B H12F . . 109.5 ?
    H12D C12B H12E . . 109.5 ?
    H12D C12B H12F . . 109.5 ?
    H12E C12B H12F . . 109.5 ?
    C7B C11B H11D . . 109.5 ?
    C7B C11B H11E . . 109.5 ?
    C7B C11B H11F . . 109.5 ?
    H11D C11B H11E . . 109.5 ?
    H11D C11B H11F . . 109.5 ?
    H11E C11B H11F . . 109.5 ?
    C2B C13B H13D . . 109.5 ?
    C2B C13B H13E . . 109.5 ?
    C2B C13B H13F . . 109.5 ?
    H13D C13B H13E . . 109.5 ?
    H13D C13B H13F . . 109.5 ?
    H13E C13B H13F . . 109.5 ?
    O2B C14B O3B . . 122.5(2) ?
    O2B C14B C3B . . 126.3(2) ?
    O3B C14B C3B . . 111.2(2) ?
    O3B C15B H15C . . 110.2 ?
    O3B C15B H15D . . 110.2 ?
    O3B C15B C16B . . 107.5(2) ?
    H15C C15B H15D . . 108.5 ?
    C16B C15B H15C . . 110.2 ?
    C16B C15B H15D . . 110.2 ?
    C15B C16B H16D . . 109.5 ?
    C15B C16B H16E . . 109.5 ?
    C15B C16B H16F . . 109.5 ?
    H16D C16B H16E . . 109.5 ?
    H16D C16B H16F . . 109.5 ?
    H16E C16B H16F . . 109.5 ?
    C18B C17B C4B . . 124.7(2) ?
    C18B C17B C22B . . 116.4(2) ?
    C22B C17B C4B . . 118.9(2) ?
    C17B C18B Br1B . . 121.88(19) ?
    C19B C18B Br1B . . 115.91(19) ?
    C19B C18B C17B . . 122.2(2) ?
    C18B C19B H19B . . 120.2 ?
    C20B C19B C18B . . 119.6(2) ?
    C20B C19B H19B . . 120.2 ?
    C19B C20B H20B . . 120.1 ?
    C19B C20B C21B . . 119.9(2) ?
    C21B C20B H20B . . 120.1 ?
    C20B C21B H21B . . 120.2 ?
    C22B C21B C20B . . 119.6(2) ?
    C22B C21B H21B . . 120.2 ?
    C17B C22B H22B . . 118.9 ?
    C21B C22B C17B . . 122.2(2) ?
    C21B C22B H22B . . 118.9 ?
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
    Br1A C18A C19A C20A . . . . 179.88(19) ?
    N1A C2A C3A C4A . . . . 2.6(4) ?
    N1A C2A C3A C14A . . . . -178.9(2) ?
    N1A C9A C8A C7A . . . . 157.0(2) ?
    C2A N1A C9A C10A . . . . -2.6(4) ?
    C2A N1A C9A C8A . . . . 177.8(2) ?
    C2A C3A C4A C10A . . . . -14.1(3) ?
    C2A C3A C4A C17A . . . . 105.6(3) ?
    C2A C3A C14A O2A . . . . 19.8(4) ?
    C2A C3A C14A O3A . . . . -160.9(2) ?
    C3A C4A C10A C9A . . . . 18.3(3) ?
    C3A C4A C10A C5A . . . . -168.2(2) ?
    C3A C4A C17A C18A . . . . 120.5(2) ?
    C3A C4A C17A C22A . . . . -64.0(3) ?
    C4A C3A C14A O2A . . . . -161.7(2) ?
    C4A C3A C14A O3A . . . . 17.7(3) ?
    C4A C10A C9A N1A . . . . -11.2(3) ?
    C4A C10A C9A C8A . . . . 168.4(2) ?
    C4A C10A C5A O1A . . . . 10.3(3) ?
    C4A C10A C5A C6A . . . . -170.6(2) ?
    C4A C17A C18A Br1A . . . . -6.1(3) ?
    C4A C17A C18A C19A . . . . 174.5(2) ?
    C4A C17A C22A C21A . . . . -173.7(2) ?
    C10A C4A C17A C18A . . . . -117.9(2) ?
    C10A C4A C17A C22A . . . . 57.6(3) ?
    C10A C9A C8A C7A . . . . -22.6(3) ?
    C9A N1A C2A C3A . . . . 7.0(4) ?
    C9A N1A C2A C13A . . . . -173.5(2) ?
    C9A C10A C5A O1A . . . . -176.1(2) ?
    C9A C10A C5A C6A . . . . 3.0(3) ?
    C9A C8A C7A C6A . . . . 48.6(3) ?
    C9A C8A C7A C11A . . . . -71.7(3) ?
    C9A C8A C7A C12A . . . . 168.2(2) ?
    C8A C7A C6A C5A . . . . -51.3(3) ?
    C7A C6A C5A O1A . . . . -154.2(2) ?
    C7A C6A C5A C10A . . . . 26.7(3) ?
    C5A C10A C9A N1A . . . . 175.5(2) ?
    C5A C10A C9A C8A . . . . -4.9(4) ?
    C11A C7A C6A C5A . . . . 69.5(3) ?
    C12A C7A C6A C5A . . . . -170.2(2) ?
    C13A C2A C3A C4A . . . . -176.8(2) ?
    C13A C2A C3A C14A . . . . 1.7(4) ?
    C14A O3A C15A C16A . . . . -88.5(3) ?
    C14A C3A C4A C10A . . . . 167.4(2) ?
    C14A C3A C4A C17A . . . . -73.0(3) ?
    C15A O3A C14A O2A . . . . 0.9(3) ?
    C15A O3A C14A C3A . . . . -178.5(2) ?
    C17A C4A C10A C9A . . . . -104.7(2) ?
    C17A C4A C10A C5A . . . . 68.8(3) ?
    C17A C18A C19A C20A . . . . -0.7(4) ?
    C18A C17A C22A C21A . . . . 2.2(4) ?
    C18A C19A C20A C21A . . . . 1.3(4) ?
    C19A C20A C21A C22A . . . . -0.2(4) ?
    C20A C21A C22A C17A . . . . -1.6(4) ?
    C22A C17A C18A Br1A . . . . 178.40(17) ?
    C22A C17A C18A C19A . . . . -1.0(3) ?
    Br1B C18B C19B C20B . . . . -179.9(2) ?
    N1B C2B C3B C4B . . . . -6.8(3) ?
    N1B C2B C3B C14B . . . . 174.0(2) ?
    N1B C9B C8B C7B . . . . -159.6(2) ?
    C2B N1B C9B C10B . . . . 12.6(4) ?
    C2B N1B C9B C8B . . . . -166.5(2) ?
    C2B C3B C4B C10B . . . . 25.5(3) ?
    C2B C3B C4B C17B . . . . -96.5(3) ?
    C2B C3B C14B O2B . . . . -9.1(4) ?
    C2B C3B C14B O3B . . . . 171.1(2) ?
    C3B C4B C10B C9B . . . . -27.2(3) ?
    C3B C4B C10B C5B . . . . 154.4(2) ?
    C3B C4B C17B C18B . . . . -122.8(2) ?
    C3B C4B C17B C22B . . . . 58.0(3) ?
    C4B C3B C14B O2B . . . . 171.8(2) ?
    C4B C3B C14B O3B . . . . -8.1(3) ?
    C4B C10B C9B N1B . . . . 10.1(3) ?
    C4B C10B C9B C8B . . . . -170.9(2) ?
    C4B C10B C5B O1B . . . . -8.5(3) ?
    C4B C10B C5B C6B . . . . 173.4(2) ?
    C4B C17B C18B Br1B . . . . -0.6(3) ?
    C4B C17B C18B C19B . . . . 179.4(2) ?
    C4B C17B C22B C21B . . . . -179.4(2) ?
    C10B C4B C17B C18B . . . . 115.4(2) ?
    C10B C4B C17B C22B . . . . -63.7(3) ?
    C10B C9B C8B C7B . . . . 21.4(3) ?
    C9B N1B C2B C3B . . . . -14.3(4) ?
    C9B N1B C2B C13B . . . . 165.5(2) ?
    C9B C10B C5B O1B . . . . 173.1(2) ?
    C9B C10B C5B C6B . . . . -5.0(3) ?
    C9B C8B C7B C6B . . . . -49.2(3) ?
    C9B C8B C7B C12B . . . . -167.8(2) ?
    C9B C8B C7B C11B . . . . 72.0(3) ?
    C8B C7B C6B C5B . . . . 52.6(3) ?
    C7B C6B C5B O1B . . . . 155.3(2) ?
    C7B C6B C5B C10B . . . . -26.5(3) ?
    C5B C10B C9B N1B . . . . -171.5(2) ?
    C5B C10B C9B C8B . . . . 7.5(4) ?
    C12B C7B C6B C5B . . . . 170.7(2) ?
    C11B C7B C6B C5B . . . . -68.8(3) ?
    C13B C2B C3B C4B . . . . 173.5(2) ?
    C13B C2B C3B C14B . . . . -5.7(4) ?
    C14B O3B C15B C16B . . . . 177.9(2) ?
    C14B C3B C4B C10B . . . . -155.3(2) ?
    C14B C3B C4B C17B . . . . 82.7(3) ?
    C15B O3B C14B O2B . . . . 2.9(3) ?
    C15B O3B C14B C3B . . . . -177.29(19) ?
    C17B C4B C10B C9B . . . . 96.4(3) ?
    C17B C4B C10B C5B . . . . -82.0(3) ?
    C17B C18B C19B C20B . . . . 0.1(4) ?
    C18B C17B C22B C21B . . . . 1.4(4) ?
    C18B C19B C20B C21B . . . . 1.3(4) ?
    C19B C20B C21B C22B . . . . -1.3(4) ?
    C20B C21B C22B C17B . . . . -0.1(4) ?
    C22B C17B C18B Br1B . . . . 178.55(17) ?
    C22B C17B C18B C19B . . . . -1.4(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
    N1B H1B O1A 2_645 0.80(3) 2.02(3) 2.818(3) 174(3)
    N1A H1A O1B 2 0.83(3) 2.07(3) 2.884(3) 165(2)
_shelxl_version_number         .2013
data_global
_journal_date_recd_electronic     2014-04-25
_journal_date_accepted     2014-07-04
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2014
_journal_volume     70
_journal_issue      8
_journal_page_first     790
_journal_page_last     795
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229614015617
_journal_coeditor_code     SF3233
_publ_contact_author_name     'Nicholas R. Natale'
_publ_contact_author_address
;
Department of Biomedical and Pharmaceutical Sciences
University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
_publ_contact_author_email     nicholas.natale@mso.umt.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '406-243-4132'
_publ_section_title
;
The effect of bromine scanning around the phenyl group of 4-phenylquinolone
derivatives
;
loop_
    _publ_author_name
    _publ_author_address
    'Steiger, Scott A.'
;
Department of Biomedical and Pharmaceutical Sciences
University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
    'Monacelli, Anthony J.'
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Li, Chun'
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Hunting, Janet L.'
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Natale, Nicholas R.'
;
Department of Biomedical and Pharmaceutical Sciences
University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
_publ_section_synopsis
;
In three quinolone compounds, the 1,4-dihydropyridine (1,4-DHP) rings adopt
flat boat conformations which are bisected by the plane of the pseudo-axial
brominated aryl ring. The cyclohexanone rings adopt an envelope conformation.
The packing of all three compounds is linked through intermolecular N---H...O
hydrogen bonds.
;
