#------------------------------------------------------------------------------
#$Date: 2022-01-27 11:50:49 +0200 (Thu, 27 Jan 2022) $
#$Revision: 272275 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038966.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_4038966
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            'C24 H12 Cr2 O12 S3'
_chemical_formula_weight         692.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                104.632(4)
_cell_angle_beta                 94.044(4)
_cell_angle_gamma                96.766(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7699(7)
_cell_length_b                   10.8891(11)
_cell_length_c                   17.2416(17)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.46
_cell_volume                     1394.0(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.712
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_min         2.455
_diffrn_source                   'I\ms micro focus'
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       blade
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0309
_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)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3603
_reflns_number_total             4749
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1111112.cif
_cod_data_source_block           PCOD1111112
_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_database_code               4038966
_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, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cr1 Cr 0.93707(5) 0.53057(3) 0.67056(3) 0.01683(13) Uani 1 1 d . . . . .
Cr2 Cr 0.49471(5) 0.06642(4) 0.16197(3) 0.01715(13) Uani 1 1 d . . . . .
S1 S 0.44286(8) 0.23548(6) 0.68379(4) 0.01626(17) Uani 1 1 d . . . . .
S2 S 0.20802(8) 0.01951(5) 0.54699(4) 0.01579(17) Uani 1 1 d . . . . .
S3 S 0.16544(8) -0.06104(5) 0.35743(4) 0.01587(17) Uani 1 1 d . . . . .
O1 O 0.9331(3) 0.79610(16) 0.78002(13) 0.0307(5) Uani 1 1 d . . . . .
O2 O 1.1918(3) 0.4836(2) 0.79852(14) 0.0419(6) Uani 1 1 d . . . . .
O3 O 1.2254(3) 0.66133(18) 0.59924(13) 0.0362(5) Uani 1 1 d . . . . .
O4 O 1.0181(3) 0.28772(17) 0.55469(13) 0.0324(5) Uani 1 1 d . . . . .
O5 O 0.6827(3) 0.59589(17) 0.54994(14) 0.0362(6) Uani 1 1 d . . . . .
O6 O 0.6743(2) 0.43357(15) 0.77659(11) 0.0200(4) Uani 1 1 d . . . . .
O7 O 0.5012(3) 0.34083(17) 0.26160(13) 0.0293(5) Uani 1 1 d . . . . .
O8 O 0.7799(3) 0.02117(18) 0.27678(13) 0.0312(5) Uani 1 1 d . . . . .
O9 O 0.7767(3) 0.16955(19) 0.07309(13) 0.0379(6) Uani 1 1 d . . . . .
O10 O 0.5115(3) -0.20550(18) 0.06371(14) 0.0400(6) Uani 1 1 d . . . . .
O11 O 0.2252(3) 0.12475(18) 0.04471(13) 0.0332(5) Uani 1 1 d . . . . .
O12 O 0.1622(2) -0.08320(16) 0.19921(12) 0.0254(5) Uani 1 1 d . . . . .
C1 C 0.9257(3) 0.6937(2) 0.74056(18) 0.0202(6) Uani 1 1 d . . . . .
C2 C 1.0941(4) 0.4990(2) 0.75059(19) 0.0257(7) Uani 1 1 d . . . . .
C3 C 1.1183(4) 0.6118(2) 0.62833(18) 0.0233(7) Uani 1 1 d . . . . .
C4 C 0.9823(3) 0.3773(2) 0.59848(18) 0.0204(6) Uani 1 1 d . . . . .
C5 C 0.7763(4) 0.5692(2) 0.59442(19) 0.0216(7) Uani 1 1 d . . . . .
C6 C 0.7253(3) 0.4289(2) 0.70443(17) 0.0152(6) Uani 1 1 d . . . . .
C7 C 0.7557(4) 0.5273(2) 0.84926(16) 0.0232(7) Uani 1 1 d . . . . .
H7A H 0.768343 0.614395 0.840834 0.028 Uiso 1 1 calc R U . . .
H7B H 0.872583 0.507728 0.864510 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6390(5) 0.5194(3) 0.9136(2) 0.0450(9) Uani 1 1 d . . . . .
H8A H 0.524738 0.540963 0.898260 0.067 Uiso 1 1 calc R U . . .
H8B H 0.690432 0.579826 0.964503 0.067 Uiso 1 1 calc R U . . .
H8C H 0.625151 0.432077 0.920224 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6032(3) 0.3295(2) 0.64761(16) 0.0143(6) Uani 1 1 d . . . . .
C10 C 0.5929(3) 0.2932(2) 0.56533(16) 0.0148(6) Uani 1 1 d . . . . .
H10 H 0.667849 0.333448 0.535015 0.018 Uiso 1 1 calc R U . . .
C11 C 0.4603(3) 0.1906(2) 0.52997(16) 0.0133(6) Uani 1 1 d . . . . .
C12 C 0.3710(3) 0.1485(2) 0.58726(16) 0.0136(6) Uani 1 1 d . . . . .
C13 C 0.2564(3) 0.0252(2) 0.45086(16) 0.0139(6) Uani 1 1 d . . . . .
C14 C 0.3930(3) 0.1181(2) 0.44993(16) 0.0140(6) Uani 1 1 d . . . . .
C15 C 0.4280(3) 0.1170(2) 0.37096(16) 0.0146(6) Uani 1 1 d . . . . .
H15 H 0.518751 0.173374 0.358729 0.018 Uiso 1 1 calc R U . . .
C16 C 0.3178(3) 0.0263(2) 0.31327(16) 0.0140(6) Uani 1 1 d . . . . .
C17 C 0.3078(3) -0.0022(2) 0.22621(17) 0.0168(6) Uani 1 1 d . . . . .
C18 C 0.4965(3) 0.2370(2) 0.22541(17) 0.0197(6) Uani 1 1 d . . . . .
C19 C 0.6709(4) 0.0388(2) 0.23469(18) 0.0203(7) Uani 1 1 d . . . . .
C20 C 0.6699(4) 0.1294(2) 0.10635(18) 0.0231(7) Uani 1 1 d . . . . .
C21 C 0.5013(4) -0.1034(3) 0.09950(18) 0.0234(7) Uani 1 1 d . . . . .
C22 C 0.3226(4) 0.0998(2) 0.08861(18) 0.0219(7) Uani 1 1 d . . . . .
C23 C 0.0902(4) -0.1268(3) 0.11594(19) 0.0361(8) Uani 1 1 d . . . . .
H23A H 0.183963 -0.145671 0.080553 0.043 Uiso 1 1 calc R U . . .
H23B H 0.029707 -0.060046 0.100517 0.043 Uiso 1 1 calc R U . . .
C24 C -0.0337(5) -0.2437(3) 0.1078(2) 0.0571(11) Uani 1 1 d . . . . .
H24A H -0.093270 -0.271865 0.052954 0.086 Uiso 1 1 calc R U . . .
H24B H -0.119809 -0.225520 0.146544 0.086 Uiso 1 1 calc R U . . .
H24C H 0.029450 -0.311449 0.118449 0.086 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'
Cr Cr 0.3209 0.6236 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 Cr1 C1 86.49(11) . .
C3 Cr1 C4 85.54(11) . .
C1 Cr1 C4 171.52(11) . .
C3 Cr1 C2 91.73(12) . .
C1 Cr1 C2 88.74(12) . .
C4 Cr1 C2 88.61(12) . .
C3 Cr1 C5 88.93(12) . .
C1 Cr1 C5 88.47(11) . .
C4 Cr1 C5 94.28(12) . .
C2 Cr1 C5 177.08(11) . .
C3 Cr1 C6 173.61(12) . .
C1 Cr1 C6 98.26(10) . .
C4 Cr1 C6 89.91(10) . .
C2 Cr1 C6 92.65(11) . .
C5 Cr1 C6 86.92(11) . .
C20 Cr2 C19 88.80(12) . .
C20 Cr2 C21 90.42(11) . .
C19 Cr2 C21 87.14(12) . .
C20 Cr2 C18 88.39(11) . .
C19 Cr2 C18 91.26(11) . .
C21 Cr2 C18 178.03(12) . .
C20 Cr2 C22 89.54(12) . .
C19 Cr2 C22 177.92(11) . .
C21 Cr2 C22 94.13(12) . .
C18 Cr2 C22 87.43(11) . .
C20 Cr2 C17 178.18(12) . .
C19 Cr2 C17 89.45(11) . .
C21 Cr2 C17 89.97(10) . .
C18 Cr2 C17 91.17(10) . .
C22 Cr2 C17 92.20(11) . .
C12 S1 C9 90.34(12) . .
C12 S2 C13 89.11(12) . .
C13 S3 C16 90.19(12) . .
C6 O6 C7 123.1(2) . .
C17 O12 C23 124.8(2) . .
O1 C1 Cr1 173.4(2) . .
O2 C2 Cr1 177.8(3) . .
O3 C3 Cr1 177.0(3) . .
O4 C4 Cr1 176.4(2) . .
O5 C5 Cr1 177.9(2) . .
O6 C6 C9 106.1(2) . .
O6 C6 Cr1 130.46(19) . .
C9 C6 Cr1 123.41(19) . .
O6 C7 C8 106.5(2) . .
O6 C7 H7A 110.4 . .
C8 C7 H7A 110.4 . .
O6 C7 H7B 110.4 . .
C8 C7 H7B 110.4 . .
H7A C7 H7B 108.6 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C6 129.0(2) . .
C10 C9 S1 111.23(19) . .
C6 C9 S1 119.8(2) . .
C9 C10 C11 113.4(2) . .
C9 C10 H10 123.3 . .
C11 C10 H10 123.3 . .
C12 C11 C10 111.9(2) . .
C12 C11 C14 111.5(2) . .
C10 C11 C14 136.6(2) . .
C11 C12 S1 113.09(19) . .
C11 C12 S2 114.0(2) . .
S1 C12 S2 132.95(16) . .
C14 C13 S3 113.7(2) . .
C14 C13 S2 114.2(2) . .
S3 C13 S2 132.12(15) . .
C13 C14 C15 111.7(2) . .
C13 C14 C11 111.3(2) . .
C15 C14 C11 137.0(2) . .
C16 C15 C14 113.1(2) . .
C16 C15 H15 123.4 . .
C14 C15 H15 123.4 . .
C15 C16 C17 130.0(2) . .
C15 C16 S3 111.2(2) . .
C17 C16 S3 118.76(18) . .
O12 C17 C16 105.6(2) . .
O12 C17 Cr2 129.2(2) . .
C16 C17 Cr2 125.06(18) . .
O7 C18 Cr2 177.5(2) . .
O8 C19 Cr2 178.1(2) . .
O9 C20 Cr2 179.0(2) . .
O10 C21 Cr2 177.2(3) . .
O11 C22 Cr2 176.7(2) . .
O12 C23 C24 107.1(3) . .
O12 C23 H23A 110.3 . .
C24 C23 H23A 110.3 . .
O12 C23 H23B 110.3 . .
C24 C23 H23B 110.3 . .
H23A C23 H23B 108.5 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cr1 C3 1.864(3) .
Cr1 C1 1.894(3) .
Cr1 C4 1.898(3) .
Cr1 C2 1.900(3) .
Cr1 C5 1.906(3) .
Cr1 C6 2.075(3) .
Cr2 C20 1.881(3) .
Cr2 C19 1.892(3) .
Cr2 C21 1.899(3) .
Cr2 C18 1.900(3) .
Cr2 C22 1.905(3) .
Cr2 C17 2.070(3) .
S1 C12 1.711(3) .
S1 C9 1.766(2) .
S2 C12 1.739(3) .
S2 C13 1.740(3) .
S3 C13 1.702(3) .
S3 C16 1.764(2) .
O1 C1 1.143(3) .
O2 C2 1.140(4) .
O3 C3 1.151(3) .
O4 C4 1.150(3) .
O5 C5 1.134(3) .
O6 C6 1.323(3) .
O6 C7 1.450(3) .
O7 C18 1.140(3) .
O8 C19 1.142(3) .
O9 C20 1.147(3) .
O10 C21 1.142(3) .
O11 C22 1.136(3) .
O12 C17 1.326(3) .
O12 C23 1.442(3) .
C6 C9 1.457(4) .
C7 C8 1.494(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.367(4) .
C10 C11 1.406(3) .
C10 H10 0.9500 .
C11 C12 1.385(3) .
C11 C14 1.432(4) .
C13 C14 1.381(3) .
C14 C15 1.405(4) .
C15 C16 1.372(3) .
C15 H15 0.9500 .
C16 C17 1.448(4) .
C23 C24 1.473(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C7 O6 C6 C9 -175.5(2) . . . .
C7 O6 C6 Cr1 6.7(3) . . . .
C6 O6 C7 C8 168.1(2) . . . .
O6 C6 C9 C10 175.5(2) . . . .
Cr1 C6 C9 C10 -6.5(4) . . . .
O6 C6 C9 S1 -5.6(3) . . . .
Cr1 C6 C9 S1 172.42(12) . . . .
C12 S1 C9 C10 1.32(19) . . . .
C12 S1 C9 C6 -177.82(19) . . . .
C6 C9 C10 C11 178.4(2) . . . .
S1 C9 C10 C11 -0.6(3) . . . .
C9 C10 C11 C12 -0.6(3) . . . .
C9 C10 C11 C14 179.2(3) . . . .
C10 C11 C12 S1 1.7(3) . . . .
C14 C11 C12 S1 -178.17(16) . . . .
C10 C11 C12 S2 -178.88(16) . . . .
C14 C11 C12 S2 1.3(3) . . . .
C9 S1 C12 C11 -1.71(18) . . . .
C9 S1 C12 S2 178.99(19) . . . .
C13 S2 C12 C11 -1.70(18) . . . .
C13 S2 C12 S1 177.59(19) . . . .
C16 S3 C13 C14 1.36(18) . . . .
C16 S3 C13 S2 -179.49(18) . . . .
C12 S2 C13 C14 1.75(18) . . . .
C12 S2 C13 S3 -177.39(18) . . . .
S3 C13 C14 C15 -1.6(3) . . . .
S2 C13 C14 C15 179.08(16) . . . .
S3 C13 C14 C11 177.93(16) . . . .
S2 C13 C14 C11 -1.4(3) . . . .
C12 C11 C14 C13 0.1(3) . . . .
C10 C11 C14 C13 -179.7(3) . . . .
C12 C11 C14 C15 179.4(3) . . . .
C10 C11 C14 C15 -0.4(5) . . . .
C13 C14 C15 C16 1.0(3) . . . .
C11 C14 C15 C16 -178.4(3) . . . .
C14 C15 C16 C17 177.9(2) . . . .
C14 C15 C16 S3 0.0(3) . . . .
C13 S3 C16 C15 -0.76(18) . . . .
C13 S3 C16 C17 -178.93(19) . . . .
C23 O12 C17 C16 173.0(2) . . . .
C23 O12 C17 Cr2 -9.8(4) . . . .
C15 C16 C17 O12 -170.1(2) . . . .
S3 C16 C17 O12 7.7(3) . . . .
C15 C16 C17 Cr2 12.6(4) . . . .
S3 C16 C17 Cr2 -169.57(11) . . . .
C17 O12 C23 C24 161.8(2) . . . .
