#------------------------------------------------------------------------------
#$Date: 2022-01-27 11:51:43 +0200 (Thu, 27 Jan 2022) $
#$Revision: 272279 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038970.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_4038970
loop_
_publ_author_name
'Lamprecht, Zandria'
'Malan, Frederick P.'
'Liles, David C.'
'Lotz, Simon'
'Bezuidenhout, Daniela I.'
_publ_section_title
;
 Synthesis and structure of annulated
 dithieno[2,3-b;3ʹ,2ʹ-d]thienyl- and ring-opened
 3,3ʹ-bithienyl Fischer carbene complexes
;
_journal_name_full               'Journal of Organometallic Chemistry'
_journal_page_first              121466
_journal_paper_doi               10.1016/j.jorganchem.2020.121466
_journal_volume                  925
_journal_year                    2020
_chemical_formula_sum            'C16 H9 N O5 S3 W'
_chemical_formula_weight         572.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.372(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5378(6)
_cell_length_b                   6.4155(2)
_cell_length_c                   15.0044(4)
_cell_measurement_reflns_used    19327
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.2420
_cell_measurement_theta_min      2.7670
_cell_volume                     1855.62(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW System, HyPix'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1421
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20159
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.113
_diffrn_source                   'Rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    6.589
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019) was used
for absorption correction. Empirical absorption correction using
spherical harmonics, implemented in SCALE3 ABSPACK scaling algoritm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_description       blade
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.211
_refine_diff_density_max         3.316
_refine_diff_density_min         -2.793
_refine_diff_density_rms         0.251
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0528
_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)+(0.0708P)²+17.3235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3529
_reflns_number_total             3788
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1111116.cif
_cod_data_source_block           PCOD1111116
_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 built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038970
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.84631(2) 0.62407(5) 0.25763(2) 0.02045(15) Uani 1 1 d . . . . .
S1 S 0.71891(14) 0.7740(4) 0.44660(17) 0.0418(6) Uani 1 1 d . . . . .
S2 S 0.5610(2) 0.8590(5) 0.4554(2) 0.0597(9) Uani 1 1 d . . . . .
S3 S 0.41811(18) 0.6324(7) 0.3832(3) 0.0708(12) Uani 1 1 d . . . . .
O5 O 0.9270(4) 0.2017(10) 0.2324(5) 0.0392(15) Uani 1 1 d . . . . .
O1 O 0.7084(3) 0.4631(12) 0.1340(4) 0.0380(15) Uani 1 1 d . . . . .
O2 O 0.7613(4) 1.0459(12) 0.2548(6) 0.0483(18) Uani 1 1 d . . . . .
O4 O 0.9709(4) 0.8529(11) 0.3833(5) 0.0420(17) Uani 1 1 d . . . . .
C2 C 0.7920(5) 0.8943(13) 0.2596(7) 0.031(2) Uani 1 1 d . . . . .
N14 N 0.8378(4) 0.3867(10) 0.4463(5) 0.0268(16) Uani 1 1 d . . . . .
C5 C 0.8980(5) 0.3540(13) 0.2436(6) 0.0258(17) Uani 1 1 d . . . . .
O3 O 0.9061(4) 0.7657(13) 0.0846(5) 0.052(2) Uani 1 1 d . . . . .
C4 C 0.9274(5) 0.7655(13) 0.3385(5) 0.0285(18) Uani 1 1 d . . . . .
C6 C 0.8074(4) 0.4998(13) 0.3790(5) 0.0240(16) Uani 1 1 d . . . . .
C3 C 0.8835(5) 0.7183(14) 0.1475(6) 0.035(2) Uani 1 1 d . . . . .
C7 C 0.9100(5) 0.3286(16) 0.4569(6) 0.033(2) Uani 1 1 d . . . . .
H7A H 0.913709 0.180209 0.450894 0.050 Uiso 1 1 calc R U . . .
H7B H 0.933063 0.370588 0.515594 0.050 Uiso 1 1 calc R U . . .
H7C H 0.931281 0.396256 0.411338 0.050 Uiso 1 1 calc R U . . .
C1 C 0.7586(5) 0.5125(13) 0.1791(5) 0.0255(17) Uani 1 1 d . . . . .
C8 C 0.8045(6) 0.3049(16) 0.5223(5) 0.036(2) Uani 1 1 d . . . . .
H8A H 0.755144 0.322561 0.507914 0.054 Uiso 1 1 calc R U . . .
H8B H 0.821801 0.380272 0.576579 0.054 Uiso 1 1 calc R U . . .
H8C H 0.815194 0.159604 0.531111 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6738(4) 0.4461(15) 0.3535(5) 0.0273(17) Uani 1 1 d . . . . .
H10 H 0.672078 0.325234 0.318917 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7335(4) 0.5492(14) 0.3864(5) 0.0266(17) Uani 1 1 d . . . . .
C11 C 0.6140(5) 0.5453(17) 0.3782(6) 0.035(2) Uani 1 1 d . . . . .
C12 C 0.6313(5) 0.7272(17) 0.4268(6) 0.039(2) Uani 1 1 d . . . . .
C14 C 0.5396(5) 0.5073(19) 0.3634(6) 0.041(2) Uani 1 1 d . . . . .
C15 C 0.4928(6) 0.355(2) 0.3191(8) 0.049(3) Uani 1 1 d . . . . .
H15 H 0.506725 0.238063 0.289980 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5058(6) 0.662(2) 0.4016(7) 0.047(3) Uani 1 1 d . . . . .
C16 C 0.4260(7) 0.399(3) 0.3241(9) 0.071(5) Uani 1 1 d . . . . .
H16 H 0.388699 0.316279 0.299236 0.085 Uiso 1 1 calc R U . . .
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'
W W -0.8490 6.8722 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 W1 C5 85.4(3) . .
C3 W1 C2 90.8(4) . .
C5 W1 C2 174.9(4) . .
C3 W1 C4 90.3(4) . .
C5 W1 C4 95.1(4) . .
C2 W1 C4 88.2(4) . .
C3 W1 C1 90.7(3) . .
C5 W1 C1 91.5(3) . .
C2 W1 C1 85.2(4) . .
C4 W1 C1 173.4(3) . .
C3 W1 C6 176.5(3) . .
C5 W1 C6 91.2(3) . .
C2 W1 C6 92.6(3) . .
C4 W1 C6 90.5(3) . .
C1 W1 C6 88.9(3) . .
C12 S1 C9 90.5(4) . .
C12 S2 C13 89.3(5) . .
C13 S3 C16 90.5(6) . .
O2 C2 W1 175.7(9) . .
C6 N14 C7 122.9(7) . .
C6 N14 C8 125.8(8) . .
C7 N14 C8 111.3(7) . .
O5 C5 W1 177.6(7) . .
O4 C4 W1 176.7(8) . .
N14 C6 C9 112.5(7) . .
N14 C6 W1 131.1(6) . .
C9 C6 W1 116.4(5) . .
O3 C3 W1 177.5(8) . .
O1 C1 W1 175.6(8) . .
C9 C10 C11 112.1(8) . .
C10 C9 C6 130.4(8) . .
C10 C9 S1 112.7(6) . .
C6 C9 S1 116.9(6) . .
C12 C11 C10 111.8(9) . .
C12 C11 C14 111.8(9) . .
C10 C11 C14 136.3(10) . .
C11 C12 S1 112.8(7) . .
C11 C12 S2 114.0(8) . .
S1 C12 S2 133.1(7) . .
C13 C14 C15 112.1(10) . .
C13 C14 C11 110.6(10) . .
C15 C14 C11 137.3(10) . .
C16 C15 C14 112.5(12) . .
C14 C13 S3 113.0(10) . .
C14 C13 S2 114.2(9) . .
S3 C13 S2 132.7(7) . .
C15 C16 S3 111.9(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
W1 C3 2.003(9) .
W1 C5 2.033(8) .
W1 C2 2.035(9) .
W1 C4 2.044(9) .
W1 C1 2.045(9) .
W1 C6 2.231(8) .
S1 C12 1.716(10) .
S1 C9 1.750(9) .
S2 C12 1.726(9) .
S2 C13 1.766(14) .
S3 C13 1.701(12) .
S3 C16 1.759(17) .
O5 C5 1.155(10) .
O1 C1 1.141(10) .
O2 C2 1.139(11) .
O4 C4 1.141(11) .
N14 C6 1.305(10) .
N14 C7 1.442(12) .
N14 C8 1.497(11) .
O3 C3 1.147(11) .
C6 C9 1.500(11) .
C10 C9 1.363(12) .
C10 C11 1.431(12) .
C11 C12 1.389(15) .
C11 C14 1.456(14) .
C14 C13 1.371(15) .
C14 C15 1.427(17) .
C15 C16 1.348(17) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C7 N14 C6 C9 -176.5(8) . . . .
C8 N14 C6 C9 2.0(12) . . . .
C7 N14 C6 W1 4.3(12) . . . .
C8 N14 C6 W1 -177.1(6) . . . .
C11 C10 C9 C6 178.6(8) . . . .
C11 C10 C9 S1 -1.3(10) . . . .
N14 C6 C9 C10 -91.5(11) . . . .
W1 C6 C9 C10 87.8(10) . . . .
N14 C6 C9 S1 88.5(8) . . . .
W1 C6 C9 S1 -92.2(6) . . . .
C12 S1 C9 C10 0.0(7) . . . .
C12 S1 C9 C6 -179.9(7) . . . .
C9 C10 C11 C12 2.3(11) . . . .
C9 C10 C11 C14 -179.6(10) . . . .
C10 C11 C12 S1 -2.3(11) . . . .
C14 C11 C12 S1 179.1(6) . . . .
C10 C11 C12 S2 177.9(6) . . . .
C14 C11 C12 S2 -0.6(11) . . . .
C9 S1 C12 C11 1.3(8) . . . .
C9 S1 C12 S2 -179.0(8) . . . .
C13 S2 C12 C11 0.7(8) . . . .
C13 S2 C12 S1 -179.0(9) . . . .
C12 C11 C14 C13 0.1(12) . . . .
C10 C11 C14 C13 -178.0(10) . . . .
C12 C11 C14 C15 178.9(12) . . . .
C10 C11 C14 C15 1(2) . . . .
C13 C14 C15 C16 0.6(15) . . . .
C11 C14 C15 C16 -178.2(12) . . . .
C15 C14 C13 S3 -1.4(12) . . . .
C11 C14 C13 S3 177.7(7) . . . .
C15 C14 C13 S2 -178.7(8) . . . .
C11 C14 C13 S2 0.5(11) . . . .
C16 S3 C13 C14 1.4(9) . . . .
C16 S3 C13 S2 178.0(9) . . . .
C12 S2 C13 C14 -0.7(9) . . . .
C12 S2 C13 S3 -177.2(9) . . . .
C14 C15 C16 S3 0.4(14) . . . .
C13 S3 C16 C15 -1.0(11) . . . .
