#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017304
loop_
_publ_author_name
'Blanco, Maria C.'
'Palma, Alirio'
'Bahsas, Ali'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Different hydrogen-bonded structures in three 2-thienyl-substituted
 tetrahydro-1,4-epoxy-1-benzazepines
;
_journal_coeditor_code           GG3212
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o487
_journal_page_last               o491
_journal_paper_doi               10.1107/S0108270109031199
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H15 N O S'
_chemical_formula_moiety         'C15 H15 N O S'
_chemical_formula_sum            'C15 H15 N O S'
_chemical_formula_weight         257.34
_chemical_name_systematic
;
(2RS,4SR)-2-exo-(5-methyl-2-thienyl)-2,3,4,5-
tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.3789(12)
_cell_length_b                   9.6964(14)
_cell_length_c                   30.952(4)
_cell_measurement_reflns_used    2874
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.76
_cell_volume                     2514.7(6)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            21293
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.351
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0426P)²+1.7346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1730
_reflns_number_total             2874
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3212.cif
_cod_data_source_block           II
_cod_database_code               2017304
_cod_database_fobs_code          2017304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5597(2) 0.38687(19) 0.64474(6) 0.0213(5) Uani d . 1 . .
C C2 0.7087(3) 0.4320(2) 0.62350(7) 0.0214(6) Uani d . 1 . .
H H2 0.6873 0.5194 0.6074 0.026 Uiso calc R 1 . .
C C3 0.8249(3) 0.4627(3) 0.66044(8) 0.0248(6) Uani d . 1 . .
H H3A 0.9267 0.4124 0.6566 0.030 Uiso calc R 1 . .
H H3B 0.8473 0.5627 0.6626 0.030 Uiso calc R 1 . .
C C4 0.7354(3) 0.4112(2) 0.69995(7) 0.0224(6) Uani d . 1 . .
H H4 0.8097 0.3624 0.7201 0.027 Uiso calc R 1 . .
C C5 0.6453(3) 0.5224(3) 0.72346(7) 0.0247(6) Uani d . 1 . .
H H5A 0.6059 0.4861 0.7514 0.030 Uiso calc R 1 . .
H H5B 0.7177 0.6007 0.7296 0.030 Uiso calc R 1 . .
C C5A 0.5079(3) 0.5713(2) 0.69704(7) 0.0205(5) Uani d . 1 . .
C C6 0.4156(3) 0.6832(2) 0.70913(8) 0.0253(6) Uani d . 1 . .
H H6 0.4401 0.7311 0.7351 0.030 Uiso calc R 1 . .
C C7 0.2893(3) 0.7261(3) 0.68428(8) 0.0291(6) Uani d . 1 . .
H H7 0.2272 0.8030 0.6931 0.035 Uiso calc R 1 . .
C C8 0.2524(3) 0.6579(3) 0.64653(8) 0.0305(6) Uani d . 1 . .
H H8 0.1652 0.6877 0.6293 0.037 Uiso calc R 1 . .
C C9 0.3426(3) 0.5464(3) 0.63405(8) 0.0257(6) Uani d . 1 . .
H H9 0.3179 0.4989 0.6081 0.031 Uiso calc R 1 . .
C C9A 0.4687(3) 0.5037(2) 0.65915(8) 0.0216(5) Uani d . 1 . .
O O14 0.61991(19) 0.31636(16) 0.68256(5) 0.0230(4) Uani d . 1 . .
S S21 0.62791(8) 0.23531(7) 0.562064(19) 0.02638(19) Uani d . 1 . .
C C22 0.7644(3) 0.3255(2) 0.59239(7) 0.0231(6) Uani d . 1 . .
C C23 0.9144(3) 0.2958(3) 0.57941(8) 0.0271(6) Uani d . 1 . .
H H23 1.0069 0.3347 0.5923 0.033 Uiso calc R 1 . .
C C24 0.9198(3) 0.2011(3) 0.54472(8) 0.0305(7) Uani d . 1 . .
H H24 1.0166 0.1699 0.5321 0.037 Uiso calc R 1 . .
C C25 0.7746(3) 0.1590(3) 0.53127(8) 0.0268(6) Uani d . 1 . .
C C26 0.7350(4) 0.0578(3) 0.49695(8) 0.0360(7) Uani d . 1 . .
H H26A 0.8242 0.0514 0.4765 0.054 Uiso calc R 1 . .
H H26B 0.6389 0.0880 0.4816 0.054 Uiso calc R 1 . .
H H26C 0.7159 -0.0327 0.5100 0.054 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9A N1 O14 . . 107.86(17) ?
C9A N1 C2 . . 110.68(18) ?
O14 N1 C2 . . 101.83(16) ?
N1 C2 C22 . . 110.36(19) ?
N1 C2 C3 . . 105.25(18) ?
C22 C2 C3 . . 114.8(2) ?
N1 C2 H2 . . 108.8 ?
C22 C2 H2 . . 108.8 ?
C3 C2 H2 . . 108.8 ?
C4 C3 C2 . . 102.88(19) ?
C4 C3 H3A . . 111.2 ?
C2 C3 H3A . . 111.2 ?
C4 C3 H3B . . 111.2 ?
C2 C3 H3B . . 111.2 ?
H3A C3 H3B . . 109.1 ?
O14 C4 C5 . . 107.56(19) ?
O14 C4 C3 . . 103.95(18) ?
C5 C4 C3 . . 113.7(2) ?
O14 C4 H4 . . 110.5 ?
C5 C4 H4 . . 110.5 ?
C3 C4 H4 . . 110.5 ?
C5A C5 C4 . . 110.52(19) ?
C5A C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C5A C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C9A C5A C6 . . 118.0(2) ?
C9A C5A C5 . . 119.8(2) ?
C6 C5A C5 . . 122.2(2) ?
C7 C6 C5A . . 121.1(2) ?
C7 C6 H6 . . 119.4 ?
C5A C6 H6 . . 119.4 ?
C6 C7 C8 . . 120.2(2) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 119.5(2) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C9A . . 120.0(2) ?
C8 C9 H9 . . 120.0 ?
C9A C9 H9 . . 120.0 ?
C9 C9A C5A . . 121.2(2) ?
C9 C9A N1 . . 118.0(2) ?
C5A C9A N1 . . 120.8(2) ?
C4 O14 N1 . . 103.62(16) ?
C22 S21 C25 . . 92.63(13) ?
C23 C22 C2 . . 129.3(2) ?
C23 C22 S21 . . 110.39(19) ?
C2 C22 S21 . . 119.87(19) ?
C22 C23 C24 . . 113.2(2) ?
C22 C23 H23 . . 123.4 ?
C24 C23 H23 . . 123.4 ?
C25 C24 C23 . . 113.7(2) ?
C25 C24 H24 . . 123.2 ?
C23 C24 H24 . . 123.2 ?
C24 C25 C26 . . 128.5(2) ?
C24 C25 S21 . . 110.05(19) ?
C26 C25 S21 . . 121.4(2) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9A . 1.436(3) ?
N1 O14 . 1.446(2) ?
N1 C2 . 1.477(3) ?
C2 C22 . 1.487(3) ?
C2 C3 . 1.531(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.519(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 O14 . 1.439(3) ?
C4 C5 . 1.504(3) ?
C4 H4 . 1.0000 ?
C5 C5A . 1.490(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5A C9A . 1.383(3) ?
C5A C6 . 1.383(3) ?
C6 C7 . 1.373(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.378(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.375(3) ?
C8 H8 . 0.9500 ?
C9 C9A . 1.375(3) ?
C9 H9 . 0.9500 ?
S21 C22 . 1.719(3) ?
S21 C25 . 1.722(3) ?
C22 C23 . 1.350(3) ?
C23 C24 . 1.414(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.349(4) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.484(3) ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 Cg1 7_765 1.00 2.59 3.570(2) 167 no
C3 H3B O14 7_765 0.99 2.55 3.527(3) 169 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A N1 C2 C22 . . . . -154.6(2) ?
O14 N1 C2 C22 . . . . 90.9(2) ?
C9A N1 C2 C3 . . . . 81.0(2) ?
O14 N1 C2 C3 . . . . -33.4(2) ?
N1 C2 C3 C4 . . . . 7.9(2) ?
C22 C2 C3 C4 . . . . -113.6(2) ?
C2 C3 C4 O14 . . . . 20.7(2) ?
C2 C3 C4 C5 . . . . -95.9(2) ?
O14 C4 C5 C5A . . . . -45.4(2) ?
C3 C4 C5 C5A . . . . 69.1(3) ?
C4 C5 C5A C9A . . . . 7.3(3) ?
C4 C5 C5A C6 . . . . -173.0(2) ?
C9A C5A C6 C7 . . . . -0.2(3) ?
C5 C5A C6 C7 . . . . -179.8(2) ?
C5A C6 C7 C8 . . . . -0.1(4) ?
C6 C7 C8 C9 . . . . 0.2(4) ?
C7 C8 C9 C9A . . . . 0.0(4) ?
C8 C9 C9A C5A . . . . -0.3(4) ?
C8 C9 C9A N1 . . . . -179.9(2) ?
C6 C5A C9A C9 . . . . 0.4(3) ?
C5 C5A C9A C9 . . . . -179.9(2) ?
C6 C5A C9A N1 . . . . 180.0(2) ?
C5 C5A C9A N1 . . . . -0.3(3) ?
O14 N1 C9A C9 . . . . -149.5(2) ?
C2 N1 C9A C9 . . . . 100.0(2) ?
O14 N1 C9A C5A . . . . 30.9(3) ?
C2 N1 C9A C5A . . . . -79.7(3) ?
C5 C4 O14 N1 . . . . 77.9(2) ?
C3 C4 O14 N1 . . . . -42.9(2) ?
C9A N1 O14 C4 . . . . -68.7(2) ?
C2 N1 O14 C4 . . . . 47.79(19) ?
N1 C2 C22 C23 . . . . -151.1(2) ?
C3 C2 C22 C23 . . . . -32.4(4) ?
N1 C2 C22 S21 . . . . 37.7(3) ?
C3 C2 C22 S21 . . . . 156.38(17) ?
C25 S21 C22 C23 . . . . -0.7(2) ?
C25 S21 C22 C2 . . . . 171.97(19) ?
C2 C22 C23 C24 . . . . -171.4(2) ?
S21 C22 C23 C24 . . . . 0.5(3) ?
C22 C23 C24 C25 . . . . 0.2(3) ?
C23 C24 C25 C26 . . . . -177.9(2) ?
C23 C24 C25 S21 . . . . -0.7(3) ?
C22 S21 C25 C24 . . . . 0.8(2) ?
C22 S21 C25 C26 . . . . 178.2(2) ?
