#------------------------------------------------------------------------------
#$Date: 2022-01-27 11:51:05 +0200 (Thu, 27 Jan 2022) $
#$Revision: 272276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038967.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_4038967
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            'C9 H6.5 Cr0.5 N0.5 O2.5 S1.5'
_chemical_formula_weight         235.74
_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                110.742(3)
_cell_angle_beta                 91.017(3)
_cell_angle_gamma                103.342(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4794(7)
_cell_length_b                   11.9763(11)
_cell_length_c                   12.1963(12)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.82
_cell_volume                     988.15(16)
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0199
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28214
_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         26.022
_diffrn_reflns_theta_min         2.816
_diffrn_source                   'I\ms micro focus'
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.788
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0285
_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)+(0.0288P)²+1.0784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3429
_reflns_number_total             3883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1111113.cif
_cod_data_source_block           PCOD1111113
_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_formula_sum        'C9 H6.50 Cr0.50 N0.50 O2.50 S1.50'
_cod_database_code               4038967
_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.
;
_shelx_estimated_absorpt_t_min   0.756
_shelx_estimated_absorpt_t_max   0.973
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 0.36170(4) 0.92104(3) 0.69843(3) 0.01726(9) Uani 1 1 d . . . . .
S1 S 0.22689(7) 0.48265(4) 0.56180(4) 0.02080(12) Uani 1 1 d . . . . .
S2 S 0.20810(7) 0.27615(4) 0.31371(5) 0.02380(12) Uani 1 1 d . . . . .
O1 O 0.6535(2) 0.99152(16) 0.90228(14) 0.0352(4) Uani 1 1 d . . . . .
O2 O 0.0625(2) 0.99151(15) 0.85595(15) 0.0399(4) Uani 1 1 d . . . . .
O3 O 0.4632(2) 1.19111(14) 0.73371(18) 0.0465(5) Uani 1 1 d . . . . .
O4 O 0.6793(2) 0.90133(16) 0.54843(15) 0.0378(4) Uani 1 1 d . . . . .
O5 O 0.25645(19) 0.68309(12) 0.75330(12) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.0783(2) 0.85050(16) 0.47591(15) 0.0255(4) Uani 1 1 d . . . . .
C1 C 0.5381(3) 0.96197(18) 0.82681(18) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.1724(3) 0.95880(18) 0.79783(18) 0.0248(4) Uani 1 1 d . . . . .
C3 C 0.4221(3) 1.0869(2) 0.7175(2) 0.0283(5) Uani 1 1 d . . . . .
C4 C 0.5553(3) 0.90350(18) 0.60210(18) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.2971(2) 0.73642(17) 0.67479(16) 0.0179(4) Uani 1 1 d . . . . .
C6 C 0.2504(3) 0.7516(2) 0.87721(17) 0.0262(4) Uani 1 1 d . . . . .
H6A H 0.153911 0.797775 0.887194 0.031 Uiso 1 1 calc R U . . .
H6AB H 0.371068 0.811108 0.912559 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2064(3) 0.6583(2) 0.9349(2) 0.0327(5) Uani 1 1 d . . . . .
H7A H 0.085064 0.601637 0.900583 0.049 Uiso 1 1 calc R U . . .
H7B H 0.204489 0.700707 1.019740 0.049 Uiso 1 1 calc R U . . .
H7C H 0.300839 0.611650 0.922075 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2878(2) 0.63461(16) 0.56304(17) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.3169(2) 0.63519(17) 0.45217(16) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.351566 0.708599 0.435678 0.021 Uiso 1 1 calc R U . . .
C10 C 0.2900(2) 0.51579(17) 0.36532(17) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.2422(3) 0.42551(17) 0.41389(17) 0.0193(4) Uani 1 1 d . . . . .
C12 C 0.2576(3) 0.33430(19) 0.20284(18) 0.0237(2) Uani 1 1 d . . . . .
C13 C 0.2984(3) 0.46141(19) 0.23997(18) 0.0237(2) Uani 1 1 d . . . . .
C15 C 0.3160(3) 0.40344(18) 0.03879(18) 0.0237(2) Uani 1 1 d D . . . .
H15 H 0.331303 0.410376 -0.035896 0.028 Uiso 1 1 calc R U . A 1
C16 C 0.1805(3) 0.87648(17) 0.55815(18) 0.0209(4) Uani 1 1 d . . . . .
C17 C -0.0376(3) 0.8207(2) 0.36860(19) 0.0361(5) Uani 1 1 d . . . . .
H17A H -0.047127 0.898037 0.359396 0.043 Uiso 1 1 calc R U . . .
H17B H -0.163334 0.774953 0.374133 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0357(4) 0.7451(4) 0.2635(2) 0.0670(10) Uani 1 1 d . . . . .
H18A H -0.048504 0.725088 0.192889 0.100 Uiso 1 1 calc R U . . .
H18B H 0.046036 0.668585 0.272450 0.100 Uiso 1 1 calc R U . . .
H18C H 0.157860 0.791527 0.255638 0.100 Uiso 1 1 calc R U . . .
S3A S 0.25997(11) 0.26391(6) 0.05295(6) 0.02627(19) Uani 0.888(2) 1 d . . P B 1
C14A C 0.3370(6) 0.5001(4) 0.1346(3) 0.0237(2) Uani 0.888(2) 1 d . . P B 1
H14A H 0.371449 0.583052 0.138510 0.028 Uiso 0.888(2) 1 calc R U P B 1
C14B C 0.263(4) 0.276(3) 0.092(2) 0.0237(2) Uani 0.112(2) 1 d . . P B 2
H14B H 0.244648 0.189464 0.050269 0.028 Uiso 0.112(2) 1 calc R U P B 2
S3B S 0.3393(13) 0.5146(7) 0.1528(6) 0.02627(19) Uani 0.112(2) 1 d D . P B 2
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'
N N 0.0061 0.0033 '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 88.06(9) . .
C3 Cr1 C4 87.24(9) . .
C1 Cr1 C4 87.16(9) . .
C3 Cr1 C2 85.98(9) . .
C1 Cr1 C2 92.81(9) . .
C4 Cr1 C2 173.22(9) . .
C3 Cr1 C16 91.95(8) . .
C1 Cr1 C16 178.08(8) . .
C4 Cr1 C16 90.93(8) . .
C2 Cr1 C16 89.11(8) . .
C3 Cr1 C5 179.04(9) . .
C1 Cr1 C5 92.19(8) . .
C4 Cr1 C5 91.84(8) . .
C2 Cr1 C5 94.94(8) . .
C16 Cr1 C5 87.76(7) . .
C11 S1 C8 90.30(9) . .
C11 S2 C12 89.09(10) . .
C5 O5 C6 123.33(15) . .
C16 N1 C17 175.6(2) . .
O1 C1 Cr1 175.64(18) . .
O2 C2 Cr1 173.72(19) . .
O3 C3 Cr1 177.3(2) . .
O4 C4 Cr1 175.11(19) . .
O5 C5 C8 104.98(16) . .
O5 C5 Cr1 129.54(14) . .
C8 C5 Cr1 125.48(14) . .
O5 C6 C7 106.43(17) . .
O5 C6 H6A 110.4 . .
C7 C6 H6A 110.4 . .
O5 C6 H6AB 110.4 . .
C7 C6 H6AB 110.4 . .
H6A C6 H6AB 108.6 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C5 130.50(17) . .
C9 C8 S1 111.29(14) . .
C5 C8 S1 118.21(14) . .
C8 C9 C10 113.28(17) . .
C8 C9 H9 123.4 . .
C10 C9 H9 123.4 . .
C11 C10 C9 111.28(17) . .
C11 C10 C13 111.08(17) . .
C9 C10 C13 137.64(18) . .
C10 C11 S1 113.85(14) . .
C10 C11 S2 114.41(15) . .
S1 C11 S2 131.74(12) . .
C14B C12 C13 116.3(14) . .
C13 C12 S3A 112.79(16) . .
C14B C12 S2 128.9(14) . .
C13 C12 S2 114.73(15) . .
S3A C12 S2 132.46(13) . .
C12 C13 S3B 117.3(3) . .
C12 C13 C10 110.69(18) . .
S3B C13 C10 132.0(3) . .
C12 C13 C14A 109.5(2) . .
C10 C13 C14A 139.9(2) . .
C14A C15 S3A 116.9(2) . .
S3B C15 C14B 101.6(9) . .
C14A C15 H15 121.5 . .
S3A C15 H15 121.5 . .
N1 C16 Cr1 178.82(18) . .
N1 C17 C18 112.1(2) . .
N1 C17 H17A 109.2 . .
C18 C17 H17A 109.2 . .
N1 C17 H17B 109.2 . .
C18 C17 H17B 109.2 . .
H17A C17 H17B 107.9 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 S3A C12 90.65(10) . .
C15 C14A C13 110.1(3) . .
C15 C14A H14A 124.9 . .
C13 C14A H14A 124.9 . .
C12 C14B C15 100.9(18) . .
C12 C14B H14B 129.6 . .
C15 C14B H14B 129.6 . .
C13 S3B C15 103.7(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cr1 C3 1.860(2) .
Cr1 C1 1.875(2) .
Cr1 C4 1.883(2) .
Cr1 C2 1.910(2) .
Cr1 C16 1.996(2) .
Cr1 C5 2.0630(19) .
S1 C11 1.704(2) .
S1 C8 1.7656(18) .
S2 C11 1.7285(19) .
S2 C12 1.737(2) .
O1 C1 1.148(2) .
O2 C2 1.142(3) .
O3 C3 1.156(3) .
O4 C4 1.145(3) .
O5 C5 1.331(2) .
O5 C6 1.449(2) .
N1 C16 1.153(3) .
N1 C17 1.441(3) .
C5 C8 1.459(3) .
C6 C7 1.499(3) .
C6 H6A 0.9900 .
C6 H6AB 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.376(3) .
C9 C10 1.412(3) .
C9 H9 0.9500 .
C10 C11 1.389(3) .
C10 C13 1.443(3) .
C12 C14B 1.29(3) .
C12 C13 1.381(3) .
C12 S3A 1.723(2) .
C13 S3B 1.425(10) .
C13 C14A 1.525(5) .
C15 C14A 1.297(4) .
C15 S3B 1.520(5) .
C15 S3A 1.698(2) .
C15 C14B 1.84(3) .
C15 H15 0.9500 .
C17 C18 1.481(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C14A H14A 0.9500 .
C14B H14B 0.9500 .
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
C6 O5 C5 C8 179.87(16) . . . .
C6 O5 C5 Cr1 0.1(3) . . . .
C5 O5 C6 C7 -178.09(17) . . . .
O5 C5 C8 C9 179.95(19) . . . .
Cr1 C5 C8 C9 -0.3(3) . . . .
O5 C5 C8 S1 1.02(19) . . . .
Cr1 C5 C8 S1 -179.20(9) . . . .
C11 S1 C8 C9 -0.03(15) . . . .
C11 S1 C8 C5 179.10(15) . . . .
C5 C8 C9 C10 -178.56(18) . . . .
S1 C8 C9 C10 0.4(2) . . . .
C8 C9 C10 C11 -0.7(2) . . . .
C8 C9 C10 C13 179.2(2) . . . .
C9 C10 C11 S1 0.7(2) . . . .
C13 C10 C11 S1 -179.28(13) . . . .
C9 C10 C11 S2 -179.59(13) . . . .
C13 C10 C11 S2 0.4(2) . . . .
C8 S1 C11 C10 -0.38(15) . . . .
C8 S1 C11 S2 179.96(15) . . . .
C12 S2 C11 C10 -0.29(15) . . . .
C12 S2 C11 S1 179.36(15) . . . .
C11 S2 C12 C14B 179.3(16) . . . .
C11 S2 C12 C13 0.06(16) . . . .
C11 S2 C12 S3A -177.91(17) . . . .
C14B C12 C13 S3B 1.0(15) . . . .
S2 C12 C13 S3B -179.7(4) . . . .
C14B C12 C13 C10 -179.1(14) . . . .
S3A C12 C13 C10 178.54(14) . . . .
S2 C12 C13 C10 0.2(2) . . . .
S3A C12 C13 C14A -1.1(3) . . . .
S2 C12 C13 C14A -179.4(2) . . . .
C11 C10 C13 C12 -0.4(2) . . . .
C9 C10 C13 C12 179.7(2) . . . .
C11 C10 C13 S3B 179.4(5) . . . .
C9 C10 C13 S3B -0.5(6) . . . .
C11 C10 C13 C14A 179.0(3) . . . .
C9 C10 C13 C14A -0.9(5) . . . .
C14A C15 S3A C12 1.0(3) . . . .
C13 C12 S3A C15 0.15(17) . . . .
S2 C12 S3A C15 178.15(16) . . . .
S3A C15 C14A C13 -1.8(4) . . . .
C12 C13 C14A C15 1.8(4) . . . .
C10 C13 C14A C15 -177.7(2) . . . .
C13 C12 C14B C15 -2.8(18) . . . .
S2 C12 C14B C15 178.0(2) . . . .
S3B C15 C14B C12 3.6(17) . . . .
C12 C13 S3B C15 1.8(7) . . . .
C10 C13 S3B C15 -178.0(2) . . . .
C14B C15 S3B C13 -3.0(11) . . . .
