#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017305.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_2017305
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 H14 Cl N O S'
_chemical_formula_moiety         'C15 H14 Cl N O S'
_chemical_formula_sum            'C15 H14 Cl N O S'
_chemical_formula_weight         291.78
_chemical_name_systematic
;
(2RS,4SR)-7-chloro-2-exo-(5-methyl-2-thienyl)-
2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.120(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.042(3)
_cell_length_b                   15.739(3)
_cell_length_c                   5.6216(13)
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.93
_cell_volume                     1310.2(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            19866
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0423
_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)+(0.0322P)²+1.0475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                2221
_reflns_number_total             3002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3212.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017305
_cod_database_fobs_code          2017305
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.73005(12) 0.43670(12) 0.7210(3) 0.0173(4) Uani d . 1 . .
C C2 0.76448(14) 0.51566(14) 0.8526(4) 0.0180(5) Uani d . 1 . .
H H2 0.7121 0.5473 0.8969 0.022 Uiso calc R 1 . .
C C3 0.82369(15) 0.48258(14) 1.0860(4) 0.0207(5) Uani d . 1 . .
H H3A 0.8845 0.5086 1.1098 0.025 Uiso calc R 1 . .
H H3B 0.7956 0.4950 1.2287 0.025 Uiso calc R 1 . .
C C4 0.82872(14) 0.38782(14) 1.0453(4) 0.0189(5) Uani d . 1 . .
H H4 0.8915 0.3667 1.1030 0.023 Uiso calc R 1 . .
C C5 0.76197(15) 0.33740(15) 1.1593(4) 0.0200(5) Uani d . 1 . .
H H5A 0.7737 0.2759 1.1451 0.024 Uiso calc R 1 . .
H H5B 0.7688 0.3517 1.3330 0.024 Uiso calc R 1 . .
C C5a 0.66807(14) 0.35771(14) 1.0347(4) 0.0175(4) Uani d . 1 . .
C C6 0.59271(15) 0.33102(14) 1.1247(4) 0.0209(5) Uani d . 1 . .
H H6 0.5995 0.2979 1.2681 0.025 Uiso calc R 1 . .
C C7 0.50801(16) 0.35275(15) 1.0056(4) 0.0222(5) Uani d . 1 . .
C C8 0.49530(16) 0.39888(16) 0.7953(4) 0.0262(5) Uani d . 1 . .
H H8 0.4362 0.4132 0.7154 0.031 Uiso calc R 1 . .
C C9 0.56965(15) 0.42391(15) 0.7029(4) 0.0236(5) Uani d . 1 . .
H H9 0.5622 0.4549 0.5557 0.028 Uiso calc R 1 . .
C C9a 0.65535(14) 0.40423(14) 0.8227(4) 0.0177(4) Uani d . 1 . .
O O14 0.80492(10) 0.37915(10) 0.7860(2) 0.0185(3) Uani d . 1 . .
S S21 0.92305(4) 0.56314(4) 0.68127(10) 0.02117(14) Uani d . 1 . .
C C22 0.81031(14) 0.57139(14) 0.6971(4) 0.0186(5) Uani d . 1 . .
C C23 0.77158(16) 0.63253(14) 0.5455(4) 0.0215(5) Uani d . 1 . .
H H23 0.7095 0.6473 0.5278 0.026 Uiso calc R 1 . .
C C24 0.83209(16) 0.67250(15) 0.4158(4) 0.0231(5) Uani d . 1 . .
H H24 0.8146 0.7165 0.3016 0.028 Uiso calc R 1 . .
C C25 0.91722(15) 0.64224(14) 0.4695(4) 0.0203(5) Uani d . 1 . .
C C26 0.99841(16) 0.66793(16) 0.3671(4) 0.0270(5) Uani d . 1 . .
H H26A 0.9842 0.7185 0.2659 0.041 Uiso calc R 1 . .
H H26B 1.0159 0.6214 0.2690 0.041 Uiso calc R 1 . .
H H26C 1.0484 0.6807 0.4992 0.041 Uiso calc R 1 . .
Cl Cl7 0.41442(4) 0.32083(4) 1.12421(11) 0.03082(17) Uani d . 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 . . 107.80(16) ?
C9a N1 C2 . . 109.01(16) ?
O14 N1 C2 . . 102.12(14) ?
C22 C2 N1 . . 110.84(16) ?
C22 C2 C3 . . 116.15(18) ?
N1 C2 C3 . . 103.83(17) ?
C22 C2 H2 . . 108.6 ?
N1 C2 H2 . . 108.6 ?
C3 C2 H2 . . 108.6 ?
C4 C3 C2 . . 103.95(17) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O14 C4 C5 . . 108.27(17) ?
O14 C4 C3 . . 103.63(17) ?
C5 C4 C3 . . 113.55(18) ?
O14 C4 H4 . . 110.4 ?
C5 C4 H4 . . 110.4 ?
C3 C4 H4 . . 110.4 ?
C5a C5 C4 . . 109.43(18) ?
C5a C5 H5A . . 109.8 ?
C4 C5 H5A . . 109.8 ?
C5a C5 H5B . . 109.8 ?
C4 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.2 ?
C9a C5a C6 . . 118.5(2) ?
C9a C5a C5 . . 119.52(19) ?
C6 C5a C5 . . 121.98(19) ?
C7 C6 C5a . . 119.6(2) ?
C7 C6 H6 . . 120.2 ?
C5a C6 H6 . . 120.2 ?
C8 C7 C6 . . 121.9(2) ?
C8 C7 Cl7 . . 119.02(18) ?
C6 C7 Cl7 . . 119.07(18) ?
C9 C8 C7 . . 118.6(2) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
C8 C9 C9a . . 120.3(2) ?
C8 C9 H9 . . 119.9 ?
C9a C9 H9 . . 119.9 ?
C9 C9a C5a . . 121.0(2) ?
C9 C9a N1 . . 116.95(19) ?
C5a C9a N1 . . 122.01(19) ?
N1 O14 C4 . . 103.92(14) ?
C25 S21 C22 . . 92.90(11) ?
C23 C22 C2 . . 126.7(2) ?
C23 C22 S21 . . 109.99(17) ?
C2 C22 S21 . . 123.25(16) ?
C22 C23 C24 . . 113.5(2) ?
C22 C23 H23 . . 123.2 ?
C24 C23 H23 . . 123.2 ?
C25 C24 C23 . . 113.6(2) ?
C25 C24 H24 . . 123.2 ?
C23 C24 H24 . . 123.2 ?
C24 C25 C26 . . 128.7(2) ?
C24 C25 S21 . . 110.01(17) ?
C26 C25 S21 . . 121.23(17) ?
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 . 1.441(3) ?
N1 O14 . 1.441(2) ?
N1 C2 . 1.492(3) ?
C2 C22 . 1.490(3) ?
C2 C3 . 1.541(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.513(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 O14 . 1.445(2) ?
C4 C5 . 1.508(3) ?
C4 H4 . 1.0000 ?
C5 C5a . 1.497(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5a C9a . 1.383(3) ?
C5a C6 . 1.386(3) ?
C6 C7 . 1.374(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.372(3) ?
C7 Cl7 . 1.735(2) ?
C8 C9 . 1.371(3) ?
C8 H8 . 0.9500 ?
C9 C9a . 1.381(3) ?
C9 H9 . 0.9500 ?
S21 C25 . 1.714(2) ?
S21 C22 . 1.719(2) ?
C22 C23 . 1.348(3) ?
C23 C24 . 1.410(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.350(3) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.495(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 Cl7 3_667 1.00 2.80 3.742(2) 156 no
C3 H3B Cg1 1_556 0.99 2.70 3.372(3) 125 no
C5 H5A O14 4_566 0.99 2.58 3.518(3) 158 no
c5 H5B O14 1_556 0.99 2.55 3.530(3) 173 no
C6 H6 CG2 4_566 0.95 2.92 3.689(3) 139 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 . . . . -154.72(18) ?
O14 N1 C2 C22 . . . . 91.41(19) ?
C9a N1 C2 C3 . . . . 79.88(19) ?
O14 N1 C2 C3 . . . . -33.99(19) ?
C22 C2 C3 C4 . . . . -113.3(2) ?
N1 C2 C3 C4 . . . . 8.6(2) ?
C2 C3 C4 O14 . . . . 19.8(2) ?
C2 C3 C4 C5 . . . . -97.4(2) ?
O14 C4 C5 C5a . . . . -47.7(2) ?
C3 C4 C5 C5a . . . . 66.8(2) ?
C4 C5 C5a C9a . . . . 10.5(3) ?
C4 C5 C5a C6 . . . . -169.8(2) ?
C9a C5a C6 C7 . . . . -1.4(3) ?
C5 C5a C6 C7 . . . . 178.8(2) ?
C5a C6 C7 C8 . . . . 1.5(3) ?
C5a C6 C7 Cl7 . . . . -178.59(17) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
Cl7 C7 C8 C9 . . . . 179.94(19) ?
C7 C8 C9 C9a . . . . -1.2(4) ?
C8 C9 C9a C5a . . . . 1.3(3) ?
C8 C9 C9a N1 . . . . -176.7(2) ?
C6 C5a C9a C9 . . . . 0.1(3) ?
C5 C5a C9a C9 . . . . 179.9(2) ?
C6 C5a C9a N1 . . . . 178.0(2) ?
C5 C5a C9a N1 . . . . -2.2(3) ?
O14 N1 C9a C9 . . . . -151.67(19) ?
C2 N1 C9a C9 . . . . 98.2(2) ?
O14 N1 C9a C5a . . . . 30.3(3) ?
C2 N1 C9a C5a . . . . -79.8(2) ?
C9a N1 O14 C4 . . . . -66.53(18) ?
C2 N1 O14 C4 . . . . 48.23(18) ?
C5 C4 O14 N1 . . . . 78.36(19) ?
C3 C4 O14 N1 . . . . -42.50(19) ?
N1 C2 C22 C23 . . . . 89.6(3) ?
C3 C2 C22 C23 . . . . -152.2(2) ?
N1 C2 C22 S21 . . . . -88.3(2) ?
C3 C2 C22 S21 . . . . 29.9(3) ?
C25 S21 C22 C23 . . . . -0.10(18) ?
C25 S21 C22 C2 . . . . 178.07(18) ?
C2 C22 C23 C24 . . . . -177.8(2) ?
S21 C22 C23 C24 . . . . 0.3(2) ?
C22 C23 C24 C25 . . . . -0.4(3) ?
C23 C24 C25 C26 . . . . 179.1(2) ?
C23 C24 C25 S21 . . . . 0.3(3) ?
C22 S21 C25 C24 . . . . -0.11(18) ?
C22 S21 C25 C26 . . . . -179.02(19) ?
