#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/06/7120618.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7120618
loop_
_publ_author_name
'Zhang, Youquan'
'Yu, aimin'
'jia, jiru'
'Ma, Shanshan'
'Li, Ke'
'Wei, Yin'
'Meng, Xiangtai'
_publ_section_title
;
 NaH promoted [4+3] annulation of crotonate-derived sulfur ylides and
 thioaurones: synthesis of 2,5-dihydrobenzo[4,5] thieno[3,2-b]oxepine
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04466F
_journal_year                    2017
_chemical_formula_sum            'C20 H15 Br O3 S'
_chemical_formula_weight         415.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-04-25 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.942(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.811(4)
_cell_length_b                   7.488(4)
_cell_length_c                   13.687(7)
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     859.1(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8802
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  0.7511
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                3347
_reflns_number_total             3576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04466f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7120618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.20161(3) 0.35398(4) 0.183518(15) 0.02870(8) Uani 1 1 d .
S1 S 0.42477(6) 0.47709(8) 0.66735(4) 0.01650(12) Uani 1 1 d .
O1 O 0.02290(16) 0.2261(2) 0.54295(11) 0.0151(3) Uani 1 1 d .
O2 O 0.1214(2) 0.3997(3) 0.93727(12) 0.0332(6) Uani 1 1 d .
O3 O -0.13981(18) 0.3808(3) 0.85697(11) 0.0261(4) Uani 1 1 d .
C1 C 0.3864(2) 0.4473(3) 0.53581(16) 0.0149(4) Uani 1 1 d .
C2 C 0.4798(3) 0.5014(3) 0.47482(18) 0.0197(5) Uani 1 1 d .
H2 H 0.5795 0.5587 0.5049 0.024 Uiso 1 1 calc R
C3 C 0.4249(3) 0.4703(4) 0.37046(18) 0.0212(5) Uani 1 1 d .
H3 H 0.4862 0.5074 0.3278 0.025 Uiso 1 1 calc R
C4 C 0.2786(2) 0.3839(4) 0.32775(15) 0.0192(5) Uani 1 1 d .
C5 C 0.1860(2) 0.3269(3) 0.38690(15) 0.0152(5) Uani 1 1 d .
H5 H 0.0877 0.2671 0.3564 0.018 Uiso 1 1 calc R
C6 C 0.2402(2) 0.3591(4) 0.49239(13) 0.0141(4) Uani 1 1 d .
C7 C 0.1645(2) 0.3189(3) 0.56885(15) 0.0129(5) Uani 1 1 d .
C8 C 0.2469(2) 0.3708(4) 0.66444(14) 0.0142(4) Uani 1 1 d .
C9 C 0.2096(2) 0.3329(4) 0.76339(14) 0.0137(4) Uani 1 1 d .
H9 H 0.2715 0.4211 0.8153 0.016 Uiso 1 1 calc R
C10 C 0.0350(2) 0.3556(4) 0.75619(13) 0.0144(4) Uani 1 1 d .
C11 C -0.0922(2) 0.3519(4) 0.67300(14) 0.0158(4) Uani 1 1 d .
H11 H -0.1910 0.3706 0.6858 0.019 Uiso 1 1 calc R
C12 C -0.1055(2) 0.3234(3) 0.56243(15) 0.0159(5) Uani 1 1 d .
H12A H -0.2063 0.2589 0.5292 0.019 Uiso 1 1 calc R
H12B H -0.1133 0.4416 0.5289 0.019 Uiso 1 1 calc R
C13 C 0.2723(2) 0.1480(3) 0.80244(15) 0.0137(4) Uani 1 1 d .
C14 C 0.1867(3) -0.0055(4) 0.76270(19) 0.0227(5) Uani 1 1 d .
H14 H 0.0855 0.0049 0.7119 0.027 Uiso 1 1 calc R
C15 C 0.2465(3) -0.1725(4) 0.79603(19) 0.0264(6) Uani 1 1 d .
H15 H 0.1857 -0.2759 0.7688 0.032 Uiso 1 1 calc R
C16 C 0.3949(3) -0.1905(3) 0.86905(17) 0.0211(5) Uani 1 1 d .
H16 H 0.4366 -0.3056 0.8913 0.025 Uiso 1 1 calc R
C17 C 0.4808(3) -0.0400(4) 0.90887(16) 0.0186(5) Uani 1 1 d .
H17 H 0.5823 -0.0511 0.9593 0.022 Uiso 1 1 calc R
C18 C 0.4199(3) 0.1289(3) 0.87578(16) 0.0167(5) Uani 1 1 d .
H18 H 0.4804 0.2321 0.9039 0.020 Uiso 1 1 calc R
C19 C 0.0124(2) 0.3808(4) 0.85981(16) 0.0183(5) Uani 1 1 d .
C20 C -0.1694(3) 0.4065(4) 0.95441(19) 0.0361(8) Uani 1 1 d .
H20A H -0.1456 0.2957 0.9944 0.054 Uiso 1 1 calc R
H20B H -0.2816 0.4384 0.9422 0.054 Uiso 1 1 calc R
H20C H -0.1011 0.5026 0.9926 0.054 Uiso 1 1 calc R
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'
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'
Br Br -0.2901 2.4595 '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
C1 S1 C8 91.78(10)
C7 O1 C12 113.51(17)
C19 O3 C20 116.05(18)
C2 C1 C6 120.9(2)
C2 C1 S1 128.10(18)
C6 C1 S1 110.98(15)
C3 C2 C1 119.1(2)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 119.6(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 122.2(2)
C5 C4 Br1 119.18(17)
C3 C4 Br1 118.60(16)
C4 C5 C6 118.5(2)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 119.72(18)
C5 C6 C7 129.1(2)
C1 C6 C7 111.18(17)
C8 C7 O1 124.86(18)
C8 C7 C6 114.64(19)
O1 C7 C6 120.42(17)
C7 C8 C9 128.0(2)
C7 C8 S1 111.42(15)
C9 C8 S1 120.30(14)
C8 C9 C10 114.48(16)
C8 C9 C13 109.18(19)
C10 C9 C13 112.0(2)
C8 C9 H9 106.9
C10 C9 H9 106.9
C13 C9 H9 106.9
C11 C10 C19 119.27(17)
C11 C10 C9 128.50(17)
C19 C10 C9 112.22(16)
C10 C11 C12 130.66(17)
C10 C11 H11 114.7
C12 C11 H11 114.7
O1 C12 C11 116.04(17)
O1 C12 H12A 108.3
C11 C12 H12A 108.3
O1 C12 H12B 108.3
C11 C12 H12B 108.3
H12A C12 H12B 107.4
C18 C13 C14 118.3(2)
C18 C13 C9 120.4(2)
C14 C13 C9 121.26(19)
C15 C14 C13 120.9(2)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C16 120.4(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C17 C16 C15 119.2(2)
C17 C16 H16 120.4
C15 C16 H16 120.4
C16 C17 C18 120.4(2)
C16 C17 H17 119.8
C18 C17 H17 119.8
C13 C18 C17 120.7(2)
C13 C18 H18 119.6
C17 C18 H18 119.6
O2 C19 O3 123.46(19)
O2 C19 C10 123.10(19)
O3 C19 C10 113.43(17)
O3 C20 H20A 109.5
O3 C20 H20B 109.5
H20A C20 H20B 109.5
O3 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.893(2)
S1 C1 1.741(2)
S1 C8 1.748(2)
O1 C7 1.376(2)
O1 C12 1.438(2)
O2 C19 1.200(3)
O3 C19 1.330(3)
O3 C20 1.448(3)
C1 C2 1.400(3)
C1 C6 1.406(3)
C2 C3 1.379(3)
C2 H2 0.9500
C3 C4 1.399(3)
C3 H3 0.9500
C4 C5 1.382(3)
C5 C6 1.395(3)
C5 H5 0.9500
C6 C7 1.435(3)
C7 C8 1.343(3)
C8 C9 1.515(3)
C9 C10 1.521(3)
C9 C13 1.525(4)
C9 H9 1.0000
C10 C11 1.330(3)
C10 C19 1.503(3)
C11 C12 1.497(3)
C11 H11 0.9500
C12 H12A 0.9900
C12 H12B 0.9900
C13 C18 1.384(3)
C13 C14 1.390(3)
C14 C15 1.379(4)
C14 H14 0.9500
C15 C16 1.386(3)
C15 H15 0.9500
C16 C17 1.373(3)
C16 H16 0.9500
C17 C18 1.394(4)
C17 H17 0.9500
C18 H18 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
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
C8 S1 C1 C2 179.5(2)
C8 S1 C1 C6 0.4(2)
C6 C1 C2 C3 1.3(4)
S1 C1 C2 C3 -177.69(19)
C1 C2 C3 C4 -0.7(4)
C2 C3 C4 C5 -0.3(4)
C2 C3 C4 Br1 176.8(2)
C3 C4 C5 C6 0.8(4)
Br1 C4 C5 C6 -176.36(19)
C4 C5 C6 C1 -0.2(4)
C4 C5 C6 C7 177.8(3)
C2 C1 C6 C5 -0.9(4)
S1 C1 C6 C5 178.3(2)
C2 C1 C6 C7 -179.2(2)
S1 C1 C6 C7 0.0(3)
C12 O1 C7 C8 63.5(3)
C12 O1 C7 C6 -120.0(2)
C5 C6 C7 C8 -178.6(3)
C1 C6 C7 C8 -0.5(3)
C5 C6 C7 O1 4.5(4)
C1 C6 C7 O1 -177.4(2)
O1 C7 C8 C9 3.3(4)
C6 C7 C8 C9 -173.3(2)
O1 C7 C8 S1 177.47(16)
C6 C7 C8 S1 0.8(3)
C1 S1 C8 C7 -0.7(2)
C1 S1 C8 C9 174.0(2)
C7 C8 C9 C10 -43.7(4)
S1 C8 C9 C10 142.6(2)
C7 C8 C9 C13 82.7(3)
S1 C8 C9 C13 -91.0(2)
C8 C9 C10 C11 21.6(4)
C13 C9 C10 C11 -103.3(3)
C8 C9 C10 C19 -159.8(2)
C13 C9 C10 C19 75.2(3)
C19 C10 C11 C12 -177.8(3)
C9 C10 C11 C12 0.7(6)
C7 O1 C12 C11 -69.4(2)
C10 C11 C12 O1 24.4(4)
C8 C9 C13 C18 96.2(2)
C10 C9 C13 C18 -135.99(19)
C8 C9 C13 C14 -81.1(2)
C10 C9 C13 C14 46.7(3)
C18 C13 C14 C15 0.5(3)
C9 C13 C14 C15 177.9(2)
C13 C14 C15 C16 -0.9(4)
C14 C15 C16 C17 0.8(4)
C15 C16 C17 C18 -0.4(3)
C14 C13 C18 C17 -0.1(3)
C9 C13 C18 C17 -177.43(19)
C16 C17 C18 C13 0.0(3)
C20 O3 C19 O2 0.3(4)
C20 O3 C19 C10 -179.4(2)
C11 C10 C19 O2 -173.9(3)
C9 C10 C19 O2 7.4(4)
C11 C10 C19 O3 5.8(4)
C9 C10 C19 O3 -172.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188020
