#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:52:48 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/74/4037417.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_4037417
loop_
_publ_author_name
'Gao, Wen-Chao'
'Liu, Tao'
'Zhang, Bing'
'Li, Xing'
'Wei, Wen-Long'
'Liu, Qiang'
'Tian, Jun'
'Chang, Hong-Hong'
_publ_section_title
;
 Synthesis of 3-Sulfenylated Coumarins:
 BF₃·Et₂O-Mediated Electrophilic Cyclization
 of Aryl Alkynoates Using N-Sulfanylsuccinimides.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11297
_journal_page_last               11304
_journal_paper_doi               10.1021/acs.joc.6b02271
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C23 H18 O2 S'
_chemical_formula_weight         358.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4070(8)
_cell_length_b                   13.2405(11)
_cell_length_c                   15.2351(14)
_cell_measurement_reflns_used    8093
_cell_measurement_temperature    258(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.97
_cell_volume                     1897.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      258(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13854
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         2.974
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6248
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0356
_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)+(0.0459P)²+0.1880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2905
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02271_si_002.cif
_cod_data_source_block           160704c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037417
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.4136(3) 0.7366(2) 0.73557(18) 0.0483(6) Uani 1 1 d . .
C2 C 0.5501(3) 0.7585(2) 0.7649(2) 0.0602(8) Uani 1 1 d . .
C3 C 0.6272(4) 0.6899(3) 0.8264(2) 0.0798(10) Uani 1 1 d . .
H3A H 0.5686 0.6767 0.8767 0.120 Uiso 1 1 calc R U
H3B H 0.7141 0.7213 0.8449 0.120 Uiso 1 1 calc R U
H3C H 0.6483 0.6275 0.7971 0.120 Uiso 1 1 calc R U
C4 C 0.6104(4) 0.8458(3) 0.7316(2) 0.0763(10) Uani 1 1 d . .
H4 H 0.7009 0.8641 0.7503 0.092 Uiso 1 1 calc R U
C5 C 0.5418(4) 0.9065(3) 0.6720(3) 0.0793(10) Uani 1 1 d . .
H5 H 0.5860 0.9647 0.6515 0.095 Uiso 1 1 calc R U
C6 C 0.4085(3) 0.8817(2) 0.6426(2) 0.0657(8) Uani 1 1 d . .
H6 H 0.3628 0.9224 0.6016 0.079 Uiso 1 1 calc R U
C7 C 0.3414(3) 0.79456(19) 0.67452(18) 0.0478(6) Uani 1 1 d . .
C8 C 0.2007(3) 0.76237(19) 0.64656(18) 0.0429(6) Uani 1 1 d . .
C9 C 0.1422(3) 0.67933(19) 0.68322(17) 0.0459(6) Uani 1 1 d . .
C10 C 0.2173(3) 0.6207(2) 0.74994(19) 0.0508(7) Uani 1 1 d . .
C11 C 0.1256(3) 0.82256(18) 0.57827(17) 0.0436(6) Uani 1 1 d . .
C12 C 0.1725(3) 0.8199(2) 0.4922(2) 0.0576(7) Uani 1 1 d . .
H12 H 0.2494 0.7794 0.4769 0.069 Uiso 1 1 calc R U
C13 C 0.1056(4) 0.8771(3) 0.4292(2) 0.0657(8) Uani 1 1 d . .
H13 H 0.1376 0.8754 0.3714 0.079 Uiso 1 1 calc R U
C14 C -0.0085(4) 0.9369(2) 0.4513(2) 0.0658(9) Uani 1 1 d . .
H14 H -0.0539 0.9752 0.4085 0.079 Uiso 1 1 calc R U
C15 C -0.0551(4) 0.9399(2) 0.5359(2) 0.0643(9) Uani 1 1 d . .
H15 H -0.1323 0.9803 0.5507 0.077 Uiso 1 1 calc R U
C16 C 0.0113(3) 0.8836(2) 0.59973(19) 0.0548(7) Uani 1 1 d . .
H16 H -0.0206 0.8865 0.6574 0.066 Uiso 1 1 calc R U
C17 C -0.0081(3) 0.5144(2) 0.6238(2) 0.0536(7) Uani 1 1 d . .
C18 C -0.1012(4) 0.4411(3) 0.6525(3) 0.0794(10) Uani 1 1 d . .
H18 H -0.1726 0.4572 0.6924 0.095 Uiso 1 1 calc R U
C19 C -0.0876(5) 0.3436(3) 0.6215(3) 0.0901(12) Uani 1 1 d . .
H19 H -0.1533 0.2953 0.6394 0.108 Uiso 1 1 calc R U
C20 C 0.0191(5) 0.3155(3) 0.5655(3) 0.0764(10) Uani 1 1 d . .
C21 C 0.0347(6) 0.2074(3) 0.5349(3) 0.1121(17) Uani 1 1 d . .
H21A H -0.0458 0.1892 0.4996 0.168 Uiso 1 1 calc R U
H21B H 0.0398 0.1635 0.5850 0.168 Uiso 1 1 calc R U
H21C H 0.1200 0.2008 0.5008 0.168 Uiso 1 1 calc R U
C22 C 0.1098(4) 0.3904(3) 0.5372(3) 0.0879(12) Uani 1 1 d . .
H22 H 0.1825 0.3745 0.4983 0.106 Uiso 1 1 calc R U
C23 C 0.0943(4) 0.4893(3) 0.5660(3) 0.0768(10) Uani 1 1 d . .
H23 H 0.1555 0.5390 0.5451 0.092 Uiso 1 1 calc R U
O1 O 0.35265(19) 0.65082(14) 0.77031(13) 0.0540(5) Uani 1 1 d . .
O2 O 0.1725(2) 0.54870(17) 0.78874(16) 0.0708(6) Uani 1 1 d . .
S1 S -0.03328(7) 0.64092(6) 0.65953(6) 0.0621(2) Uani 1 1 d . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C7 120.7(2)
O1 C1 C2 115.6(3)
C7 C1 C2 123.6(3)
C4 C2 C1 115.8(3)
C4 C2 C3 122.7(3)
C1 C2 C3 121.5(3)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C4 C2 122.6(3)
C5 C4 H4 118.7
C2 C4 H4 118.7
C6 C5 C4 120.4(3)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 119.6(3)
C5 C6 H6 120.2
C7 C6 H6 120.2
C1 C7 C6 117.9(3)
C1 C7 C8 118.8(2)
C6 C7 C8 123.3(3)
C9 C8 C7 119.2(2)
C9 C8 C11 122.1(2)
C7 C8 C11 118.7(2)
C8 C9 C10 121.6(2)
C8 C9 S1 122.1(2)
C10 C9 S1 116.20(19)
O2 C10 O1 116.5(3)
O2 C10 C9 126.6(3)
O1 C10 C9 116.9(2)
C16 C11 C12 119.1(3)
C16 C11 C8 121.1(2)
C12 C11 C8 119.8(2)
C13 C12 C11 120.1(3)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.2(3)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 119.9(3)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 120.5(3)
C14 C15 H15 119.7
C16 C15 H15 119.7
C15 C16 C11 120.2(3)
C15 C16 H16 119.9
C11 C16 H16 119.9
C23 C17 C18 119.3(3)
C23 C17 S1 121.9(2)
C18 C17 S1 118.8(3)
C17 C18 C19 119.4(4)
C17 C18 H18 120.3
C19 C18 H18 120.3
C20 C19 C18 122.4(3)
C20 C19 H19 118.8
C18 C19 H19 118.8
C19 C20 C22 116.9(3)
C19 C20 C21 121.4(4)
C22 C20 C21 121.7(4)
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C20 C22 C23 121.0(4)
C20 C22 H22 119.5
C23 C22 H22 119.5
C17 C23 C22 120.9(3)
C17 C23 H23 119.5
C22 C23 H23 119.5
C10 O1 C1 122.6(2)
C9 S1 C17 102.09(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.378(3)
C1 C7 1.384(4)
C1 C2 1.391(4)
C2 C4 1.384(5)
C2 C3 1.493(5)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.373(5)
C4 H4 0.9300
C5 C6 1.372(5)
C5 H5 0.9300
C6 C7 1.402(4)
C6 H6 0.9300
C7 C8 1.454(4)
C8 C9 1.350(4)
C8 C11 1.489(4)
C9 C10 1.461(4)
C9 S1 1.765(3)
C10 O2 1.198(3)
C10 O1 1.369(3)
C11 C16 1.384(4)
C11 C12 1.385(4)
C12 C13 1.375(4)
C12 H12 0.9300
C13 C14 1.375(5)
C13 H13 0.9300
C14 C15 1.363(5)
C14 H14 0.9300
C15 C16 1.375(4)
C15 H15 0.9300
C16 H16 0.9300
C17 C23 1.347(4)
C17 C18 1.379(4)
C17 S1 1.778(3)
C18 C19 1.380(5)
C18 H18 0.9300
C19 C20 1.370(6)
C19 H19 0.9300
C20 C22 1.378(5)
C20 C21 1.512(5)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 C23 1.389(5)
C22 H22 0.9300
C23 H23 0.9300
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
O1 C1 C2 C4 -178.7(3)
C7 C1 C2 C4 2.4(4)
O1 C1 C2 C3 3.1(4)
C7 C1 C2 C3 -175.9(3)
C1 C2 C4 C5 -1.2(5)
C3 C2 C4 C5 177.0(3)
C2 C4 C5 C6 -0.4(6)
C4 C5 C6 C7 0.9(5)
O1 C1 C7 C6 179.2(2)
C2 C1 C7 C6 -1.9(4)
O1 C1 C7 C8 -0.9(4)
C2 C1 C7 C8 178.0(3)
C5 C6 C7 C1 0.2(5)
C5 C6 C7 C8 -179.7(3)
C1 C7 C8 C9 2.5(4)
C6 C7 C8 C9 -177.6(3)
C1 C7 C8 C11 -177.6(2)
C6 C7 C8 C11 2.2(4)
C7 C8 C9 C10 -0.4(4)
C11 C8 C9 C10 179.8(2)
C7 C8 C9 S1 174.84(19)
C11 C8 C9 S1 -5.0(3)
C8 C9 C10 O2 176.8(3)
S1 C9 C10 O2 1.3(4)
C8 C9 C10 O1 -3.3(4)
S1 C9 C10 O1 -178.75(19)
C9 C8 C11 C16 72.9(3)
C7 C8 C11 C16 -107.0(3)
C9 C8 C11 C12 -108.8(3)
C7 C8 C11 C12 71.3(3)
C16 C11 C12 C13 -0.2(4)
C8 C11 C12 C13 -178.5(3)
C11 C12 C13 C14 -0.2(5)
C12 C13 C14 C15 0.3(5)
C13 C14 C15 C16 0.1(5)
C14 C15 C16 C11 -0.5(5)
C12 C11 C16 C15 0.6(4)
C8 C11 C16 C15 178.9(3)
C23 C17 C18 C19 0.0(5)
S1 C17 C18 C19 176.5(3)
C17 C18 C19 C20 2.7(6)
C18 C19 C20 C22 -3.2(6)
C18 C19 C20 C21 177.9(4)
C19 C20 C22 C23 1.2(6)
C21 C20 C22 C23 -179.9(4)
C18 C17 C23 C22 -2.0(5)
S1 C17 C23 C22 -178.3(3)
C20 C22 C23 C17 1.4(6)
O2 C10 O1 C1 -175.1(2)
C9 C10 O1 C1 5.0(4)
C7 C1 O1 C10 -3.0(4)
C2 C1 O1 C10 178.1(2)
C8 C9 S1 C17 125.0(2)
C10 C9 S1 C17 -59.6(2)
C23 C17 S1 C9 -46.2(3)
C18 C17 S1 C9 137.5(3)
