##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'from SHELXL-97'
_journal_date_recd_electronic     2012-01-17
_journal_date_accepted     2012-01-30
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2012
_journal_volume     68
_journal_issue      3
_journal_page_first     o126
_journal_page_last     o130
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270112003988
_journal_coeditor_code     YF3011
_publ_contact_author_name     'Professor Christopher Glidewell'
_publ_contact_author_address
;
University of St Andrews
Fife KY16 9ST
Scotland
;
_publ_contact_author_email     cg@st-andrews.ac.uk
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;\
Chain formation by disordered, but correlated, hydrogen bonds in
cis-(2RS,4SR)-2-(thiophen-2-yl)-2,3,4,5-tetrahydro-\
1H-1-benzazepin-4-ol and
cis-(2RS,4SR)-2-(5-methylthiophen-2-yl)-2,3,4,5-\
tetrahydro-1H-1-benzazepin-4-ol
;
loop_
    _publ_author_name
    _publ_author_address
    'Blanco, Maria Camila'
;
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
;
cis-(2RS,4SR)-2-(thiophen-2-yl)-2,3,4,5-tetrahydro-
1H-1-benzazepin-4-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H15 N O S'
_chemical_formula_sum     'C14 H15 N O S'
_chemical_formula_iupac     'C14 H15 N O S'
_chemical_formula_weight     245.34
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.5677(6)
_cell_length_b     9.8798(4)
_cell_length_c     14.7183(11)
_cell_angle_alpha     104.726(5)
_cell_angle_beta     104.033(6)
_cell_angle_gamma     103.273(4)
_cell_volume     1240.95(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5703
_cell_measurement_theta_min     3.02
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.243
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.928
_exptl_absorpt_correction_T_max     0.971
_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 area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     31492
_diffrn_reflns_av_R_equivalents     0.0492
_diffrn_reflns_av_sigmaI/netI     0.0427
_diffrn_reflns_theta_min     3.02
_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     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     5703
_reflns_number_gt     4174
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0753
_refine_ls_R_factor_gt     0.0469
_refine_ls_wR_factor_gt     0.0960
_refine_ls_wR_factor_ref     0.1080
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     5703
_refine_ls_number_parameters     332
_refine_ls_number_restraints     14
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0368P)²+0.8514P] 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     0.304
_refine_diff_density_min     -0.362
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N11 0.57949(17) 0.35352(17) 0.79018(12) 0.0213(3) Uani d . 1 1 . .
    H H11 0.6184 0.3679 0.8575 0.026 Uiso d R 1 1 . .
    C C12 0.5071(2) 0.4721(2) 0.79033(15) 0.0220(4) Uani d . 1 1 . .
    H H12 0.4045 0.4377 0.7971 0.026 Uiso calc R 1 1 . .
    C C13 0.4897(2) 0.5138(2) 0.69588(15) 0.0270(5) Uani d . 1 1 . .
    H H13A 0.4463 0.5962 0.7027 0.032 Uiso calc R 1 1 . .
    H H13B 0.5918 0.5502 0.6906 0.032 Uiso calc R 1 1 . .
    C C14 0.3919(2) 0.3918(2) 0.60033(16) 0.0315(5) Uani d . 1 1 . .
    H H14 0.2904 0.3507 0.6068 0.038 Uiso calc R 1 1 . .
    C C15 0.4587(2) 0.2674(2) 0.57434(15) 0.0301(5) Uani d . 1 1 . .
    H H15A 0.4119 0.2127 0.5025 0.036 Uiso calc R 1 1 . .
    H H15B 0.5685 0.3107 0.5870 0.036 Uiso calc R 1 1 . .
    C C15A 0.4381(2) 0.1589(2) 0.63009(14) 0.0231(4) Uani d . 1 1 . .
    C C16 0.3664(2) 0.0097(2) 0.57887(15) 0.0289(5) Uani d . 1 1 . .
    H H16 0.3244 -0.0218 0.5087 0.035 Uiso calc R 1 1 . .
    C C17 0.3538(2) -0.0950(2) 0.62665(15) 0.0296(5) Uani d . 1 1 . .
    H H17 0.3060 -0.1964 0.5896 0.036 Uiso calc R 1 1 . .
    C C18 0.4118(2) -0.0491(2) 0.72882(15) 0.0255(4) Uani d . 1 1 . .
    H H18 0.4048 -0.1194 0.7625 0.031 Uiso calc R 1 1 . .
    C C19 0.4802(2) 0.0990(2) 0.78214(14) 0.0219(4) Uani d . 1 1 . .
    H H19 0.5180 0.1297 0.8525 0.026 Uiso calc R 1 1 . .
    C C19A 0.4947(2) 0.2047(2) 0.73403(14) 0.0200(4) Uani d . 1 1 . .
    S S121 0.78925(6) 0.68992(6) 0.89056(4) 0.02729(14) Uani d . 1 1 . .
    C C122 0.6047(2) 0.6018(2) 0.88047(15) 0.0226(4) Uani d . 1 1 . .
    C C123 0.5713(2) 0.6603(2) 0.96597(16) 0.0281(5) Uani d . 1 1 . .
    H H123 0.4758 0.6281 0.9752 0.034 Uiso calc R 1 1 . .
    C C124 0.6994(3) 0.7753(2) 1.03823(17) 0.0343(5) Uani d . 1 1 . .
    H H124 0.6984 0.8278 1.1017 0.041 Uiso calc R 1 1 . .
    C C125 0.8227(2) 0.8025(2) 1.00765(16) 0.0279(5) Uani d . 1 1 . .
    H H125 0.9167 0.8757 1.0469 0.034 Uiso calc R 1 1 . .
    O O141 0.3719(2) 0.4544(2) 0.52163(14) 0.0573(6) Uani d D 1 1 . .
    H H141 0.291(4) 0.447(8) 0.484(4) 0.086 Uiso d PD 0.50 1 . .
    H H142 0.448(5) 0.508(6) 0.519(5) 0.086 Uiso d PD 0.50 1 . .
    N N21 -0.10253(17) 0.60431(16) 0.19862(11) 0.0185(3) Uani d . 1 1 A .
    H H21 -0.1256 0.6572 0.1567 0.022 Uiso d R 1 1 . .
    C C22 0.0509(2) 0.6820(2) 0.27243(14) 0.0184(4) Uani d . 1 1 . .
    H H22 0.1283 0.6592 0.2412 0.022 Uiso calc R 1 1 A .
    C C23 0.0717(2) 0.6371(2) 0.36554(14) 0.0210(4) Uani d . 1 1 A .
    H H23A -0.0019 0.6650 0.3977 0.025 Uiso calc R 1 1 . .
    H H23B 0.1744 0.6955 0.4121 0.025 Uiso calc R 1 1 . .
    C C24 0.0530(2) 0.4746(2) 0.35141(13) 0.0213(4) Uani d . 1 1 . .
    H H24 0.1261 0.4449 0.3184 0.026 Uiso calc R 1 1 A .
    C C25 -0.1074(2) 0.3751(2) 0.28838(14) 0.0215(4) Uani d . 1 1 A .
    H H25A -0.1254 0.2808 0.3023 0.026 Uiso calc R 1 1 . .
    H H25B -0.1812 0.4225 0.3077 0.026 Uiso calc R 1 1 . .
    C C25A -0.1346(2) 0.3438(2) 0.17918(14) 0.0178(4) Uani d . 1 1 . .
    C C26 -0.1659(2) 0.2007(2) 0.11713(14) 0.0210(4) Uani d . 1 1 A .
    H H26 -0.1716 0.1230 0.1445 0.025 Uiso calc R 1 1 . .
    C C27 -0.1889(2) 0.1692(2) 0.01630(15) 0.0246(4) Uani d . 1 1 . .
    H H27 -0.2111 0.0708 -0.0251 0.030 Uiso calc R 1 1 A .
    C C28 -0.1791(2) 0.2833(2) -0.02345(14) 0.0237(4) Uani d . 1 1 A .
    H H28 -0.1925 0.2631 -0.0922 0.028 Uiso calc R 1 1 . .
    C C29 -0.1499(2) 0.4262(2) 0.03672(14) 0.0204(4) Uani d . 1 1 . .
    H H29 -0.1448 0.5032 0.0088 0.025 Uiso calc R 1 1 A .
    C C29A -0.12784(19) 0.4579(2) 0.13798(13) 0.0172(4) Uani d . 1 1 A .
    S S221 -0.04453(8) 0.91973(8) 0.35191(7) 0.0301(2) Uani d PD 0.856(2) 1 A -1
    C C222 0.0727(2) 0.8446(2) 0.29924(14) 0.0200(4) Uani d PD 0.856(2) 1 A -1
    C C223 0.1810(9) 0.9491(7) 0.2895(6) 0.0255(8) Uani d PD 0.856(2) 1 A -1
    H H223 0.2556 0.9280 0.2606 0.031 Uiso calc PR 0.856(2) 1 A -1
    C C224 0.1730(4) 1.0951(3) 0.3268(4) 0.0321(7) Uani d PD 0.856(2) 1 A -1
    H H224 0.2415 1.1810 0.3261 0.039 Uiso calc PR 0.856(2) 1 A -1
    C C225 0.0551(5) 1.0954(3) 0.3634(4) 0.0308(7) Uani d PD 0.856(2) 1 A -1
    H H225 0.0311 1.1813 0.3916 0.037 Uiso calc PR 0.856(2) 1 A -1
    S S321 0.2005(13) 0.9689(10) 0.2757(10) 0.0255(8) Uani d PD 0.144(2) 1 A -2
    C C322 0.0727(2) 0.8446(2) 0.29924(14) 0.0200(4) Uani d PD 0.144(2) 1 A -2
    C C323 -0.009(2) 0.9088(16) 0.3490(19) 0.0301(2) Uani d PD 0.144(2) 1 A -2
    H H323 -0.0837 0.8566 0.3708 0.036 Uiso calc PR 0.144(2) 1 A -2
    C C324 0.028(3) 1.0642(13) 0.366(3) 0.0308(7) Uani d PD 0.144(2) 1 A -2
    H H324 -0.0179 1.1265 0.3998 0.037 Uiso calc PR 0.144(2) 1 A -2
    C C325 0.138(3) 1.1114(11) 0.327(2) 0.0321(7) Uani d PD 0.144(2) 1 A -2
    H H325 0.1757 1.2097 0.3276 0.039 Uiso calc PR 0.144(2) 1 A -2
    O O241 0.0867(2) 0.45443(18) 0.44686(11) 0.0382(4) Uani d D 1 1 A .
    H H241 0.176(2) 0.471(7) 0.476(4) 0.057 Uiso d PD 0.50 1 . .
    H H242 0.053(6) 0.503(5) 0.484(4) 0.057 Uiso d PD 0.50 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 . 1.419(2) ?
    N11 C12 . 1.492(2) ?
    N11 H11 . 0.9301 ?
    C12 C122 . 1.503(3) ?
    C12 C13 . 1.529(3) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.512(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 O141 . 1.439(3) ?
    C14 C15 . 1.519(3) ?
    C14 H14 . 1.0000 ?
    C15 C15A . 1.513(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15A C16 . 1.390(3) ?
    C15A C19A . 1.404(3) ?
    C16 C17 . 1.390(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.381(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.383(3) ?
    C18 H18 . 0.9500 ?
    C19 C19A . 1.403(3) ?
    C19 H19 . 0.9500 ?
    S121 C125 . 1.704(2) ?
    S121 C122 . 1.7322(19) ?
    C122 C123 . 1.389(3) ?
    C123 C124 . 1.428(3) ?
    C123 H123 . 0.9500 ?
    C124 C125 . 1.356(3) ?
    C124 H124 . 0.9500 ?
    C125 H125 . 0.9500 ?
    O141 H141 . 0.813(10) ?
    O141 H142 . 0.813(10) ?
    N21 C29A . 1.423(2) ?
    N21 C22 . 1.486(2) ?
    N21 H21 . 0.9237 ?
    C22 C222 . 1.504(3) ?
    C22 C23 . 1.527(3) ?
    C22 H22 . 1.0000 ?
    C23 C24 . 1.527(3) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 O241 . 1.439(2) ?
    C24 C25 . 1.528(3) ?
    C24 H24 . 1.0000 ?
    C25 C25A . 1.502(3) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C25A C26 . 1.393(3) ?
    C25A C29A . 1.405(3) ?
    C26 C27 . 1.387(3) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.391(3) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.385(3) ?
    C28 H28 . 0.9500 ?
    C29 C29A . 1.394(3) ?
    C29 H29 . 0.9500 ?
    S221 C222 . 1.7097(19) ?
    S221 C225 . 1.721(3) ?
    C222 C223 . 1.348(5) ?
    C223 C224 . 1.434(7) ?
    C223 H223 . 0.9500 ?
    C224 C225 . 1.363(4) ?
    C224 H224 . 0.9500 ?
    C225 H225 . 0.9500 ?
    S321 C325 . 1.721(5) ?
    C323 C324 . 1.435(8) ?
    C323 H323 . 0.9500 ?
    C324 C325 . 1.363(6) ?
    C324 H324 . 0.9500 ?
    C325 H325 . 0.9500 ?
    O241 H241 . 0.813(10) ?
    O241 H242 . 0.814(10) ?
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 C12 . . 120.39(15) ?
    C19A N11 H11 . . 112.6 ?
    C12 N11 H11 . . 102.3 ?
    N11 C12 C122 . . 106.48(15) ?
    N11 C12 C13 . . 112.82(16) ?
    C122 C12 C13 . . 111.17(16) ?
    N11 C12 H12 . . 108.8 ?
    C122 C12 H12 . . 108.8 ?
    C13 C12 H12 . . 108.8 ?
    C14 C13 C12 . . 115.80(17) ?
    C14 C13 H13A . . 108.3 ?
    C12 C13 H13A . . 108.3 ?
    C14 C13 H13B . . 108.3 ?
    C12 C13 H13B . . 108.3 ?
    H13A C13 H13B . . 107.4 ?
    O141 C14 C13 . . 108.25(17) ?
    O141 C14 C15 . . 109.35(19) ?
    C13 C14 C15 . . 113.28(17) ?
    O141 C14 H14 . . 108.6 ?
    C13 C14 H14 . . 108.6 ?
    C15 C14 H14 . . 108.6 ?
    C15A C15 C14 . . 115.43(17) ?
    C15A C15 H15A . . 108.4 ?
    C14 C15 H15A . . 108.4 ?
    C15A C15 H15B . . 108.4 ?
    C14 C15 H15B . . 108.4 ?
    H15A C15 H15B . . 107.5 ?
    C16 C15A C19A . . 118.22(18) ?
    C16 C15A C15 . . 120.37(18) ?
    C19A C15A C15 . . 121.38(18) ?
    C15A C16 C17 . . 122.34(19) ?
    C15A C16 H16 . . 118.8 ?
    C17 C16 H16 . . 118.8 ?
    C18 C17 C16 . . 119.0(2) ?
    C18 C17 H17 . . 120.5 ?
    C16 C17 H17 . . 120.5 ?
    C17 C18 C19 . . 120.1(2) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 H18 . . 120.0 ?
    C18 C19 C19A . . 121.05(18) ?
    C18 C19 H19 . . 119.5 ?
    C19A C19 H19 . . 119.5 ?
    C19 C19A C15A . . 119.29(18) ?
    C19 C19A N11 . . 119.45(17) ?
    C15A C19A N11 . . 120.95(17) ?
    C125 S121 C122 . . 91.96(10) ?
    C123 C122 C12 . . 128.36(18) ?
    C123 C122 S121 . . 111.23(16) ?
    C12 C122 S121 . . 120.24(14) ?
    C122 C123 C124 . . 111.09(19) ?
    C122 C123 H123 . . 124.5 ?
    C124 C123 H123 . . 124.5 ?
    C125 C124 C123 . . 113.6(2) ?
    C125 C124 H124 . . 123.2 ?
    C123 C124 H124 . . 123.2 ?
    C124 C125 S121 . . 112.10(17) ?
    C124 C125 H125 . . 124.0 ?
    S121 C125 H125 . . 124.0 ?
    C14 O141 H141 . . 125(5) ?
    C14 O141 H142 . . 116(6) ?
    H141 O141 H142 . . 118(7) ?
    C29A N21 C22 . . 116.68(14) ?
    C29A N21 H21 . . 107.2 ?
    C22 N21 H21 . . 110.3 ?
    N21 C22 C222 . . 107.55(15) ?
    N21 C22 C23 . . 112.57(15) ?
    C222 C22 C23 . . 110.00(15) ?
    N21 C22 H22 . . 108.9 ?
    C222 C22 H22 . . 108.9 ?
    C23 C22 H22 . . 108.9 ?
    C22 C23 C24 . . 116.80(15) ?
    C22 C23 H23A . . 108.1 ?
    C24 C23 H23A . . 108.1 ?
    C22 C23 H23B . . 108.1 ?
    C24 C23 H23B . . 108.1 ?
    H23A C23 H23B . . 107.3 ?
    O241 C24 C23 . . 109.16(15) ?
    O241 C24 C25 . . 108.58(16) ?
    C23 C24 C25 . . 112.50(15) ?
    O241 C24 H24 . . 108.8 ?
    C23 C24 H24 . . 108.8 ?
    C25 C24 H24 . . 108.8 ?
    C25A C25 C24 . . 112.96(15) ?
    C25A C25 H25A . . 109.0 ?
    C24 C25 H25A . . 109.0 ?
    C25A C25 H25B . . 109.0 ?
    C24 C25 H25B . . 109.0 ?
    H25A C25 H25B . . 107.8 ?
    C26 C25A C29A . . 118.94(17) ?
    C26 C25A C25 . . 120.24(16) ?
    C29A C25A C25 . . 120.82(16) ?
    C27 C26 C25A . . 121.41(18) ?
    C27 C26 H26 . . 119.3 ?
    C25A C26 H26 . . 119.3 ?
    C26 C27 C28 . . 119.22(18) ?
    C26 C27 H27 . . 120.4 ?
    C28 C27 H27 . . 120.4 ?
    C29 C28 C27 . . 120.32(18) ?
    C29 C28 H28 . . 119.8 ?
    C27 C28 H28 . . 119.8 ?
    C28 C29 C29A . . 120.52(18) ?
    C28 C29 H29 . . 119.7 ?
    C29A C29 H29 . . 119.7 ?
    C29 C29A C25A . . 119.58(17) ?
    C29 C29A N21 . . 120.08(16) ?
    C25A C29A N21 . . 120.32(16) ?
    C222 S221 C225 . . 92.49(12) ?
    C223 C222 C22 . . 128.1(3) ?
    C223 C222 S221 . . 111.0(3) ?
    C22 C222 S221 . . 120.85(13) ?
    C222 C223 C224 . . 113.6(4) ?
    C222 C223 H223 . . 123.2 ?
    C224 C223 H223 . . 123.2 ?
    C225 C224 C223 . . 111.7(3) ?
    C225 C224 H224 . . 124.2 ?
    C223 C224 H224 . . 124.2 ?
    C224 C225 S221 . . 111.2(2) ?
    C224 C225 H225 . . 124.4 ?
    S221 C225 H225 . . 124.4 ?
    C324 C323 H323 . . 123.5 ?
    C325 C324 C323 . . 111.8(6) ?
    C325 C324 H324 . . 124.1 ?
    C323 C324 H324 . . 124.1 ?
    C324 C325 S321 . . 110.8(5) ?
    C324 C325 H325 . . 124.6 ?
    S321 C325 H325 . . 124.6 ?
    C24 O241 H241 . . 116(4) ?
    C24 O241 H242 . . 112(4) ?
    H241 O241 H242 . . 108(6) ?
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 C122 . . . . 160.67(16) ?
    C19A N11 C12 C13 . . . . -77.1(2) ?
    N11 C12 C13 C14 . . . . 61.2(2) ?
    C122 C12 C13 C14 . . . . -179.29(17) ?
    C12 C13 C14 O141 . . . . 172.59(18) ?
    C12 C13 C14 C15 . . . . -66.0(2) ?
    O141 C14 C15 C15A . . . . -160.27(17) ?
    C13 C14 C15 C15A . . . . 78.9(2) ?
    C14 C15 C15A C16 . . . . 123.2(2) ?
    C14 C15 C15A C19A . . . . -58.9(3) ?
    C19A C15A C16 C17 . . . . -2.3(3) ?
    C15 C15A C16 C17 . . . . 175.69(19) ?
    C15A C16 C17 C18 . . . . 1.3(3) ?
    C16 C17 C18 C19 . . . . 0.5(3) ?
    C17 C18 C19 C19A . . . . -1.3(3) ?
    C18 C19 C19A C15A . . . . 0.3(3) ?
    C18 C19 C19A N11 . . . . -173.35(17) ?
    C16 C15A C19A C19 . . . . 1.4(3) ?
    C15 C15A C19A C19 . . . . -176.52(18) ?
    C16 C15A C19A N11 . . . . 174.99(17) ?
    C15 C15A C19A N11 . . . . -3.0(3) ?
    C12 N11 C19A C19 . . . . -121.67(19) ?
    C12 N11 C19A C15A . . . . 64.8(2) ?
    N11 C12 C122 C123 . . . . -110.7(2) ?
    C13 C12 C122 C123 . . . . 126.0(2) ?
    N11 C12 C122 S121 . . . . 64.28(18) ?
    C13 C12 C122 S121 . . . . -59.0(2) ?
    C125 S121 C122 C123 . . . . 0.52(16) ?
    C125 S121 C122 C12 . . . . -175.27(16) ?
    C12 C122 C123 C124 . . . . 174.65(19) ?
    S121 C122 C123 C124 . . . . -0.7(2) ?
    C122 C123 C124 C125 . . . . 0.6(3) ?
    C123 C124 C125 S121 . . . . -0.2(2) ?
    C122 S121 C125 C124 . . . . -0.18(17) ?
    C29A N21 C22 C222 . . . . 158.73(15) ?
    C29A N21 C22 C23 . . . . -79.95(19) ?
    N21 C22 C23 C24 . . . . 60.0(2) ?
    C222 C22 C23 C24 . . . . 179.89(16) ?
    C22 C23 C24 O241 . . . . 176.03(16) ?
    C22 C23 C24 C25 . . . . -63.4(2) ?
    O241 C24 C25 C25A . . . . -158.78(15) ?
    C23 C24 C25 C25A . . . . 80.3(2) ?
    C24 C25 C25A C26 . . . . 116.10(19) ?
    C24 C25 C25A C29A . . . . -63.4(2) ?
    C29A C25A C26 C27 . . . . 0.6(3) ?
    C25 C25A C26 C27 . . . . -178.92(17) ?
    C25A C26 C27 C28 . . . . 0.6(3) ?
    C26 C27 C28 C29 . . . . -1.4(3) ?
    C27 C28 C29 C29A . . . . 0.9(3) ?
    C28 C29 C29A C25A . . . . 0.4(3) ?
    C28 C29 C29A N21 . . . . -178.05(17) ?
    C26 C25A C29A C29 . . . . -1.1(3) ?
    C25 C25A C29A C29 . . . . 178.43(16) ?
    C26 C25A C29A N21 . . . . 177.30(16) ?
    C25 C25A C29A N21 . . . . -3.2(3) ?
    C22 N21 C29A C29 . . . . -111.87(19) ?
    C22 N21 C29A C25A . . . . 69.7(2) ?
    N21 C22 C222 C223 . . . . -121.0(5) ?
    C23 C22 C222 C223 . . . . 116.1(5) ?
    N21 C22 C222 S221 . . . . 60.73(19) ?
    C23 C22 C222 S221 . . . . -62.18(19) ?
    C225 S221 C222 C223 . . . . -1.1(5) ?
    C225 S221 C222 C22 . . . . 177.5(2) ?
    C22 C222 C223 C224 . . . . -177.2(4) ?
    S221 C222 C223 C224 . . . . 1.1(7) ?
    C222 C223 C224 C225 . . . . -0.6(8) ?
    C223 C224 C225 S221 . . . . -0.2(7) ?
    C222 S221 C225 C224 . . . . 0.7(4) ?
    C323 C324 C325 S321 . . . . -3(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
    O141 H141 O241 . 0.81(5) 1.92(5) 2.684(3) 156(5) no
    O141 H142 O141 2_666 0.81(6) 1.95(5) 2.695(3) 153(6) no
    O241 H241 O141 . 0.81(4) 1.89(3) 2.684(3) 164(7) no
    O241 H242 O241 2_566 0.81(6) 1.92(6) 2.691(3) 158(6) no
    C225 H225 O241 1_565 0.95 2.50 3.361(4) 151 no
    C223 H223 Cg 2_666 0.95 2.93 3.705(9) 140 no
data_II
_chemical_name_systematic
;
cis-(2RS,4SR)-2-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-
1H-1-benzazepin-4-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H17 N O S'
_chemical_formula_sum     'C15 H17 N O S'
_chemical_formula_iupac     'C15 H17 N O S'
_chemical_formula_weight     259.37
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.6764(5)
_cell_length_b     10.6897(3)
_cell_length_c     14.4433(5)
_cell_angle_alpha     72.018(3)
_cell_angle_beta     89.108(3)
_cell_angle_gamma     72.494(3)
_cell_volume     1350.27(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6208
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.276
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.227
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.927
_exptl_absorpt_correction_T_max     0.978
_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 area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     35561
_diffrn_reflns_av_R_equivalents     0.0563
_diffrn_reflns_av_sigmaI/netI     0.0498
_diffrn_reflns_theta_min     2.54
_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     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     6208
_reflns_number_gt     4151
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0894
_refine_ls_R_factor_gt     0.0488
_refine_ls_wR_factor_gt     0.1104
_refine_ls_wR_factor_ref     0.1311
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     6208
_refine_ls_number_parameters     339
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0614P)²+0.4841P] 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     0.288
_refine_diff_density_min     -0.432
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N11 0.24021(19) 0.65455(18) 0.78231(13) 0.0273(4) Uani d . 1 1 . .
    H H11 0.2356 0.6461 0.8448 0.033 Uiso d R 1 1 . .
    C C12 0.3754(2) 0.5492(2) 0.77167(15) 0.0258(5) Uani d . 1 1 . .
    H H12 0.4581 0.5877 0.7691 0.031 Uiso calc R 1 1 . .
    C C13 0.3661(2) 0.5111(2) 0.67924(15) 0.0260(5) Uani d . 1 1 . .
    H H13A 0.4564 0.4366 0.6790 0.031 Uiso calc R 1 1 . .
    H H13B 0.2841 0.4731 0.6818 0.031 Uiso calc R 1 1 . .
    C C14 0.3454(2) 0.6288(2) 0.58369(15) 0.0278(5) Uani d . 1 1 . .
    H H14 0.4250 0.6709 0.5829 0.033 Uiso calc R 1 1 . .
    C C15 0.2003(2) 0.7421(2) 0.56950(15) 0.0283(5) Uani d . 1 1 . .
    H H15A 0.1785 0.7951 0.4990 0.034 Uiso calc R 1 1 . .
    H H15B 0.1233 0.6983 0.5900 0.034 Uiso calc R 1 1 . .
    C C15A 0.1945(2) 0.8416(2) 0.62528(15) 0.0258(5) Uani d . 1 1 . .
    C C16 0.1595(2) 0.9830(2) 0.57486(16) 0.0300(5) Uani d . 1 1 . .
    H H16 0.1473 1.0140 0.5055 0.036 Uiso calc R 1 1 . .
    C C17 0.1420(3) 1.0798(2) 0.62367(16) 0.0326(5) Uani d . 1 1 . .
    H H17 0.1149 1.1758 0.5882 0.039 Uiso calc R 1 1 . .
    C C18 0.1645(2) 1.0342(2) 0.72469(16) 0.0294(5) Uani d . 1 1 . .
    H H18 0.1547 1.0991 0.7588 0.035 Uiso calc R 1 1 . .
    C C19 0.2013(2) 0.8942(2) 0.77609(15) 0.0266(5) Uani d . 1 1 . .
    H H19 0.2168 0.8641 0.8453 0.032 Uiso calc R 1 1 . .
    C C19A 0.2161(2) 0.7964(2) 0.72761(15) 0.0245(4) Uani d . 1 1 . .
    S S121 0.29583(7) 0.31509(6) 0.88453(4) 0.03310(16) Uani d . 1 1 . .
    C C122 0.4026(2) 0.4249(2) 0.86183(15) 0.0270(5) Uani d . 1 1 . .
    C C123 0.5030(3) 0.3838(3) 0.93808(18) 0.0414(6) Uani d . 1 1 . .
    H H123 0.5723 0.4299 0.9403 0.050 Uiso calc R 1 1 . .
    C C124 0.4954(3) 0.2655(3) 1.01439(19) 0.0465(7) Uani d . 1 1 . .
    H H124 0.5586 0.2256 1.0727 0.056 Uiso calc R 1 1 . .
    C C125 0.3904(3) 0.2152(2) 0.99657(16) 0.0343(5) Uani d . 1 1 . .
    C C126 0.3549(3) 0.0898(3) 1.06063(18) 0.0456(6) Uani d . 1 1 . .
    H H12A 0.2620 0.1195 1.0881 0.068 Uiso calc R 1 1 . .
    H H12B 0.4319 0.0373 1.1138 0.068 Uiso calc R 1 1 . .
    H H12C 0.3475 0.0312 1.0216 0.068 Uiso calc R 1 1 . .
    O O141 0.35724(18) 0.57419(17) 0.50309(11) 0.0338(4) Uani d D 1 1 . .
    H H141 0.278(3) 0.567(6) 0.490(4) 0.051 Uiso d PD 0.50 1 . .
    H H142 0.437(3) 0.523(5) 0.498(4) 0.051 Uiso d PD 0.50 1 . .
    N N21 0.24202(19) 0.40433(17) 0.19255(12) 0.0254(4) Uani d . 1 1 . .
    H H21 0.2697 0.3541 0.1535 0.031 Uiso d R 1 1 . .
    C C22 0.1690(2) 0.3321(2) 0.27366(14) 0.0235(4) Uani d . 1 1 . .
    H H22 0.0648 0.3544 0.2509 0.028 Uiso calc R 1 1 . .
    C C23 0.1755(2) 0.3775(2) 0.36417(14) 0.0262(5) Uani d . 1 1 . .
    H H23A 0.1333 0.3206 0.4175 0.031 Uiso calc R 1 1 . .
    H H23B 0.2789 0.3568 0.3855 0.031 Uiso calc R 1 1 . .
    C C24 0.0974(2) 0.5294(2) 0.35084(14) 0.0258(5) Uani d . 1 1 . .
    H H24 -0.0058 0.5520 0.3256 0.031 Uiso calc R 1 1 . .
    C C25 0.1668(2) 0.6268(2) 0.27908(15) 0.0292(5) Uani d . 1 1 . .
    H H25A 0.1361 0.7173 0.2908 0.035 Uiso calc R 1 1 . .
    H H25B 0.2738 0.5883 0.2925 0.035 Uiso calc R 1 1 . .
    C C25A 0.1282(2) 0.6499(2) 0.17348(15) 0.0251(4) Uani d . 1 1 . .
    C C26 0.0589(2) 0.7835(2) 0.11115(15) 0.0311(5) Uani d . 1 1 . .
    H H26 0.0377 0.8585 0.1367 0.037 Uiso calc R 1 1 . .
    C C27 0.0202(3) 0.8105(2) 0.01342(16) 0.0337(5) Uani d . 1 1 . .
    H H27 -0.0268 0.9026 -0.0273 0.040 Uiso calc R 1 1 . .
    C C28 0.0511(2) 0.7012(2) -0.02419(16) 0.0302(5) Uani d . 1 1 . .
    H H28 0.0227 0.7179 -0.0907 0.036 Uiso calc R 1 1 . .
    C C29 0.1232(2) 0.5678(2) 0.03515(15) 0.0260(5) Uani d . 1 1 . .
    H H29 0.1465 0.4938 0.0085 0.031 Uiso calc R 1 1 . .
    C C29A 0.1621(2) 0.5409(2) 0.13392(14) 0.0236(4) Uani d . 1 1 . .
    S S221 0.42462(6) 0.10396(6) 0.33827(4) 0.03240(16) Uani d . 1 1 . .
    C C222 0.2414(2) 0.1788(2) 0.29829(14) 0.0246(4) Uani d . 1 1 . .
    C C223 0.1818(2) 0.0798(2) 0.29496(15) 0.0276(5) Uani d . 1 1 . .
    H H223 0.0825 0.0996 0.2746 0.033 Uiso calc R 1 1 . .
    C C224 0.2827(2) -0.0561(2) 0.32484(15) 0.0296(5) Uani d . 1 1 . .
    H H224 0.2574 -0.1358 0.3262 0.036 Uiso calc R 1 1 . .
    C C225 0.4181(2) -0.0608(2) 0.35115(15) 0.0289(5) Uani d . 1 1 . .
    C C226 0.5512(3) -0.1849(2) 0.38635(19) 0.0396(6) Uani d . 1 1 . .
    H H22A 0.5223 -0.2690 0.4084 0.059 Uiso calc R 1 1 . .
    H H22B 0.6041 -0.1775 0.4407 0.059 Uiso calc R 1 1 . .
    H H22C 0.6142 -0.1892 0.3329 0.059 Uiso calc R 1 1 . .
    O O241 0.09805(19) 0.55203(17) 0.44371(11) 0.0346(4) Uani d D 1 1 . .
    H H241 0.173(3) 0.562(6) 0.461(4) 0.052 Uiso d PD 0.50 1 . .
    H H242 0.068(5) 0.495(4) 0.483(3) 0.052 Uiso d PD 0.50 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 . 1.425(3) ?
    N11 C12 . 1.489(3) ?
    N11 H11 . 0.8801 ?
    C12 C122 . 1.504(3) ?
    C12 C13 . 1.522(3) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.521(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 O141 . 1.444(2) ?
    C14 C15 . 1.521(3) ?
    C14 H14 . 1.0000 ?
    C15 C15A . 1.508(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15A C16 . 1.397(3) ?
    C15A C19A . 1.403(3) ?
    C16 C17 . 1.391(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.386(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.385(3) ?
    C18 H18 . 0.9500 ?
    C19 C19A . 1.402(3) ?
    C19 H19 . 0.9500 ?
    S121 C125 . 1.729(2) ?
    S121 C122 . 1.741(2) ?
    C122 C123 . 1.352(3) ?
    C123 C124 . 1.418(3) ?
    C123 H123 . 0.9500 ?
    C124 C125 . 1.346(3) ?
    C124 H124 . 0.9500 ?
    C125 C126 . 1.508(3) ?
    C126 H12A . 0.9800 ?
    C126 H12B . 0.9800 ?
    C126 H12C . 0.9800 ?
    O141 H141 . 0.819(10) ?
    O141 H142 . 0.816(10) ?
    N21 C29A . 1.423(3) ?
    N21 C22 . 1.487(2) ?
    N21 H21 . 0.8798 ?
    C22 C222 . 1.503(3) ?
    C22 C23 . 1.536(3) ?
    C22 H22 . 1.0000 ?
    C23 C24 . 1.523(3) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 O241 . 1.435(2) ?
    C24 C25 . 1.531(3) ?
    C24 H24 . 1.0000 ?
    C25 C25A . 1.502(3) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C25A C26 . 1.396(3) ?
    C25A C29A . 1.402(3) ?
    C26 C27 . 1.384(3) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.388(3) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.386(3) ?
    C28 H28 . 0.9500 ?
    C29 C29A . 1.399(3) ?
    C29 H29 . 0.9500 ?
    S221 C225 . 1.733(2) ?
    S221 C222 . 1.735(2) ?
    C222 C223 . 1.362(3) ?
    C223 C224 . 1.422(3) ?
    C223 H223 . 0.9500 ?
    C224 C225 . 1.352(3) ?
    C224 H224 . 0.9500 ?
    C225 C226 . 1.501(3) ?
    C226 H22A . 0.9800 ?
    C226 H22B . 0.9800 ?
    C226 H22C . 0.9800 ?
    O241 H241 . 0.818(10) ?
    O241 H242 . 0.818(10) ?
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 C12 . . 119.01(16) ?
    C19A N11 H11 . . 109.2 ?
    C12 N11 H11 . . 108.1 ?
    N11 C12 C122 . . 107.27(16) ?
    N11 C12 C13 . . 112.67(17) ?
    C122 C12 C13 . . 111.56(17) ?
    N11 C12 H12 . . 108.4 ?
    C122 C12 H12 . . 108.4 ?
    C13 C12 H12 . . 108.4 ?
    C14 C13 C12 . . 115.58(17) ?
    C14 C13 H13A . . 108.4 ?
    C12 C13 H13A . . 108.4 ?
    C14 C13 H13B . . 108.4 ?
    C12 C13 H13B . . 108.4 ?
    H13A C13 H13B . . 107.4 ?
    O141 C14 C15 . . 108.96(17) ?
    O141 C14 C13 . . 109.28(17) ?
    C15 C14 C13 . . 113.40(17) ?
    O141 C14 H14 . . 108.4 ?
    C15 C14 H14 . . 108.4 ?
    C13 C14 H14 . . 108.4 ?
    C15A C15 C14 . . 114.41(17) ?
    C15A C15 H15A . . 108.7 ?
    C14 C15 H15A . . 108.7 ?
    C15A C15 H15B . . 108.7 ?
    C14 C15 H15B . . 108.7 ?
    H15A C15 H15B . . 107.6 ?
    C16 C15A C19A . . 118.84(19) ?
    C16 C15A C15 . . 119.57(18) ?
    C19A C15A C15 . . 121.51(19) ?
    C17 C16 C15A . . 121.7(2) ?
    C17 C16 H16 . . 119.2 ?
    C15A C16 H16 . . 119.2 ?
    C18 C17 C16 . . 119.1(2) ?
    C18 C17 H17 . . 120.4 ?
    C16 C17 H17 . . 120.4 ?
    C19 C18 C17 . . 120.2(2) ?
    C19 C18 H18 . . 119.9 ?
    C17 C18 H18 . . 119.9 ?
    C18 C19 C19A . . 121.05(19) ?
    C18 C19 H19 . . 119.5 ?
    C19A C19 H19 . . 119.5 ?
    C19 C19A C15A . . 119.14(19) ?
    C19 C19A N11 . . 120.01(18) ?
    C15A C19A N11 . . 120.63(18) ?
    C125 S121 C122 . . 92.50(11) ?
    C123 C122 C12 . . 127.8(2) ?
    C123 C122 S121 . . 109.60(17) ?
    C12 C122 S121 . . 122.52(16) ?
    C122 C123 C124 . . 113.8(2) ?
    C122 C123 H123 . . 123.1 ?
    C124 C123 H123 . . 123.1 ?
    C125 C124 C123 . . 113.8(2) ?
    C125 C124 H124 . . 123.1 ?
    C123 C124 H124 . . 123.1 ?
    C124 C125 C126 . . 127.6(2) ?
    C124 C125 S121 . . 110.29(18) ?
    C126 C125 S121 . . 122.11(19) ?
    C125 C126 H12A . . 109.5 ?
    C125 C126 H12B . . 109.5 ?
    H12A C126 H12B . . 109.5 ?
    C125 C126 H12C . . 109.5 ?
    H12A C126 H12C . . 109.5 ?
    H12B C126 H12C . . 109.5 ?
    C14 O141 H141 . . 109(4) ?
    C14 O141 H142 . . 117(4) ?
    H141 O141 H142 . . 126(6) ?
    C29A N21 C22 . . 117.56(16) ?
    C29A N21 H21 . . 107.7 ?
    C22 N21 H21 . . 109.3 ?
    N21 C22 C222 . . 108.36(16) ?
    N21 C22 C23 . . 111.75(16) ?
    C222 C22 C23 . . 110.47(16) ?
    N21 C22 H22 . . 108.7 ?
    C222 C22 H22 . . 108.7 ?
    C23 C22 H22 . . 108.7 ?
    C24 C23 C22 . . 115.84(17) ?
    C24 C23 H23A . . 108.3 ?
    C22 C23 H23A . . 108.3 ?
    C24 C23 H23B . . 108.3 ?
    C22 C23 H23B . . 108.3 ?
    H23A C23 H23B . . 107.4 ?
    O241 C24 C23 . . 109.26(17) ?
    O241 C24 C25 . . 108.97(16) ?
    C23 C24 C25 . . 112.81(17) ?
    O241 C24 H24 . . 108.6 ?
    C23 C24 H24 . . 108.6 ?
    C25 C24 H24 . . 108.6 ?
    C25A C25 C24 . . 114.09(17) ?
    C25A C25 H25A . . 108.7 ?
    C24 C25 H25A . . 108.7 ?
    C25A C25 H25B . . 108.7 ?
    C24 C25 H25B . . 108.7 ?
    H25A C25 H25B . . 107.6 ?
    C26 C25A C29A . . 118.05(19) ?
    C26 C25A C25 . . 119.88(18) ?
    C29A C25A C25 . . 122.06(19) ?
    C27 C26 C25A . . 122.3(2) ?
    C27 C26 H26 . . 118.9 ?
    C25A C26 H26 . . 118.9 ?
    C26 C27 C28 . . 119.0(2) ?
    C26 C27 H27 . . 120.5 ?
    C28 C27 H27 . . 120.5 ?
    C29 C28 C27 . . 120.1(2) ?
    C29 C28 H28 . . 120.0 ?
    C27 C28 H28 . . 120.0 ?
    C28 C29 C29A . . 120.69(19) ?
    C28 C29 H29 . . 119.7 ?
    C29A C29 H29 . . 119.7 ?
    C29 C29A C25A . . 119.83(19) ?
    C29 C29A N21 . . 119.82(18) ?
    C25A C29A N21 . . 120.29(18) ?
    C225 S221 C222 . . 92.40(10) ?
    C223 C222 C22 . . 128.66(19) ?
    C223 C222 S221 . . 110.10(16) ?
    C22 C222 S221 . . 121.23(14) ?
    C222 C223 C224 . . 113.46(19) ?
    C222 C223 H223 . . 123.3 ?
    C224 C223 H223 . . 123.3 ?
    C225 C224 C223 . . 113.50(19) ?
    C225 C224 H224 . . 123.2 ?
    C223 C224 H224 . . 123.2 ?
    C224 C225 C226 . . 128.4(2) ?
    C224 C225 S221 . . 110.53(17) ?
    C226 C225 S221 . . 121.09(17) ?
    C225 C226 H22A . . 109.5 ?
    C225 C226 H22B . . 109.5 ?
    H22A C226 H22B . . 109.5 ?
    C225 C226 H22C . . 109.5 ?
    H22A C226 H22C . . 109.5 ?
    H22B C226 H22C . . 109.5 ?
    C24 O241 H241 . . 116(4) ?
    C24 O241 H242 . . 108(4) ?
    H241 O241 H242 . . 117(6) ?
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 C122 . . . . 157.80(17) ?
    C19A N11 C12 C13 . . . . -79.0(2) ?
    N11 C12 C13 C14 . . . . 61.9(2) ?
    C122 C12 C13 C14 . . . . -177.39(18) ?
    C12 C13 C14 O141 . . . . 172.74(17) ?
    C12 C13 C14 C15 . . . . -65.5(2) ?
    O141 C14 C15 C15A . . . . -159.04(18) ?
    C13 C14 C15 C15A . . . . 79.0(2) ?
    C14 C15 C15A C16 . . . . 122.8(2) ?
    C14 C15 C15A C19A . . . . -60.7(3) ?
    C19A C15A C16 C17 . . . . -1.6(3) ?
    C15 C15A C16 C17 . . . . 175.0(2) ?
    C15A C16 C17 C18 . . . . 2.1(3) ?
    C16 C17 C18 C19 . . . . -1.2(3) ?
    C17 C18 C19 C19A . . . . -0.2(3) ?
    C18 C19 C19A C15A . . . . 0.7(3) ?
    C18 C19 C19A N11 . . . . -173.98(18) ?
    C16 C15A C19A C19 . . . . 0.2(3) ?
    C15 C15A C19A C19 . . . . -176.37(19) ?
    C16 C15A C19A N11 . . . . 174.83(18) ?
    C15 C15A C19A N11 . . . . -1.8(3) ?
    C12 N11 C19A C19 . . . . -119.8(2) ?
    C12 N11 C19A C15A . . . . 65.6(2) ?
    N11 C12 C122 C123 . . . . -104.7(3) ?
    C13 C12 C122 C123 . . . . 131.4(2) ?
    N11 C12 C122 S121 . . . . 71.7(2) ?
    C13 C12 C122 S121 . . . . -52.1(2) ?
    C125 S121 C122 C123 . . . . -0.37(18) ?
    C125 S121 C122 C12 . . . . -177.40(18) ?
    C12 C122 C123 C124 . . . . 176.8(2) ?
    S121 C122 C123 C124 . . . . 0.0(3) ?
    C122 C123 C124 C125 . . . . 0.5(3) ?
    C123 C124 C125 C126 . . . . 178.6(2) ?
    C123 C124 C125 S121 . . . . -0.8(3) ?
    C122 S121 C125 C124 . . . . 0.67(19) ?
    C122 S121 C125 C126 . . . . -178.7(2) ?
    C29A N21 C22 C222 . . . . 157.27(17) ?
    C29A N21 C22 C23 . . . . -80.8(2) ?
    N21 C22 C23 C24 . . . . 63.0(2) ?
    C222 C22 C23 C24 . . . . -176.27(17) ?
    C22 C23 C24 O241 . . . . 173.16(16) ?
    C22 C23 C24 C25 . . . . -65.5(2) ?
    O241 C24 C25 C25A . . . . -160.01(18) ?
    C23 C24 C25 C25A . . . . 78.5(2) ?
    C24 C25 C25A C26 . . . . 121.0(2) ?
    C24 C25 C25A C29A . . . . -60.4(3) ?
    C29A C25A C26 C27 . . . . 1.7(3) ?
    C25 C25A C26 C27 . . . . -179.7(2) ?
    C25A C26 C27 C28 . . . . 0.0(3) ?
    C26 C27 C28 C29 . . . . -1.8(3) ?
    C27 C28 C29 C29A . . . . 1.8(3) ?
    C28 C29 C29A C25A . . . . -0.1(3) ?
    C28 C29 C29A N21 . . . . -177.12(18) ?
    C26 C25A C29A C29 . . . . -1.6(3) ?
    C25 C25A C29A C29 . . . . 179.74(18) ?
    C26 C25A C29A N21 . . . . 175.42(18) ?
    C25 C25A C29A N21 . . . . -3.2(3) ?
    C22 N21 C29A C29 . . . . -114.7(2) ?
    C22 N21 C29A C25A . . . . 68.3(2) ?
    N21 C22 C222 C223 . . . . -119.9(2) ?
    C23 C22 C222 C223 . . . . 117.4(2) ?
    N21 C22 C222 S221 . . . . 60.8(2) ?
    C23 C22 C222 S221 . . . . -61.9(2) ?
    C225 S221 C222 C223 . . . . -0.53(16) ?
    C225 S221 C222 C22 . . . . 178.93(16) ?
    C22 C222 C223 C224 . . . . -179.14(19) ?
    S221 C222 C223 C224 . . . . 0.3(2) ?
    C222 C223 C224 C225 . . . . 0.2(3) ?
    C223 C224 C225 C226 . . . . 180.0(2) ?
    C223 C224 C225 S221 . . . . -0.6(2) ?
    C222 S221 C225 C224 . . . . 0.67(17) ?
    C222 S221 C225 C226 . . . . -179.88(19) ?
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
    O141 H141 O241 . 0.82(4) 1.94(4) 2.763(3) 173(6) no
    O141 H142 O141 2_666 0.82(4) 1.95(4) 2.757(3) 168(4) no
    O241 H241 O141 . 0.82(4) 1.95(3) 2.763(3) 177(7) no
    O241 H242 O241 2_566 0.82(4) 2.02(5) 2.746(3) 149(4) no
    C223 H223 Cg 2_566 0.95 2.74 3.572(9) 147 no
