#------------------------------------------------------------------------------
#$Date: 2022-10-27 01:14:21 +0300 (Thu, 27 Oct 2022) $
#$Revision: 278817 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/09/7130914.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_7130914
loop_
_publ_author_name
'Hsieh, Chang-Chih'
'Li, Cheng-Yao'
'Chiang, Ming-Hsi'
'Horng, Yih-Chern'
_publ_section_title
;
 Catalytic O2 Activation toward Oxidative N-S Bond Formation by a Thiolato
 Fe(III) Complex
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05375F
_journal_year                    2022
_chemical_formula_sum            'C18 H18 Cl2 N2 O2 S2'
_chemical_formula_weight         429.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.2724(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7004(2)
_cell_length_b                   18.5647(4)
_cell_length_c                   11.2176(2)
_cell_measurement_reflns_used    8484
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.34
_cell_volume                     1962.54(7)
_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 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29522
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4161
_reflns_number_total             5089
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc05375f2.cif
_cod_data_source_block           compound2j
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130914
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S -0.08378(5) 0.11200(2) 0.61301(4) 0.02459(14) Uani 1 1 d . . . . .
S2 S -0.00120(5) 0.13325(2) 0.48581(4) 0.02417(14) Uani 1 1 d . . . . .
C7 C -0.2215(2) 0.15501(10) 0.78409(17) 0.0254(4) Uani 1 1 d . . . . .
C1 C 0.0863(2) 0.23069(11) 0.74554(18) 0.0293(4) Uani 1 1 d . . . . .
H1 H 0.1357 0.2214 0.6957 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0561(2) 0.25887(11) 0.89211(17) 0.0288(4) Uani 1 1 d . . . . .
H2 H -0.1048 0.2685 0.9425 0.035 Uiso 1 1 calc R U . . .
C3 C -0.02680(19) 0.18674(9) 0.72772(16) 0.0232(3) Uani 1 1 d . . . . .
C4 C -0.10098(19) 0.20175(10) 0.79967(17) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.0575(2) 0.30137(11) 0.91125(19) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.0878 0.3394 0.9755 0.041 Uiso 1 1 calc R U . . .
C8 C -0.4431(3) 0.15055(13) 0.7959(3) 0.0436(6) Uani 1 1 d . . . . .
H8A H -0.4296 0.0981 0.7909 0.052 Uiso 1 1 calc R U . . .
H8B H -0.5353 0.1639 0.7182 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1273(2) 0.28808(12) 0.83586(19) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.2033 0.3184 0.8461 0.041 Uiso 1 1 calc R U . . .
C9 C -0.4462(3) 0.16742(12) 0.9260(3) 0.0474(6) Uani 1 1 d . . . . .
H9A H -0.5239 0.1400 0.9293 0.057 Uiso 1 1 calc R U . . .
H9B H -0.4653 0.2194 0.9288 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2147(2) 0.04657(10) 0.67568(18) 0.0281(4) Uani 1 1 d . . . . .
H10 H 0.1746 0.0550 0.7340 0.034 Uiso 1 1 calc R U . . .
C11 C 0.15476(19) 0.07878(9) 0.54872(16) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.2150(2) 0.06600(9) 0.46306(16) 0.0220(3) Uani 1 1 d . . . . .
C16 C 0.1551(2) 0.10159(10) 0.32852(18) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.3331(2) 0.02110(10) 0.50720(18) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.3735 0.0120 0.4494 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3923(2) -0.01042(10) 0.63434(18) 0.0306(4) Uani 1 1 d . . . . .
H14 H 0.4734 -0.0405 0.6638 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3326(2) 0.00212(10) 0.71811(19) 0.0307(4) Uani 1 1 d . . . . .
H15 H 0.3724 -0.0197 0.8050 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0906(4) 0.0913(2) 0.0897(2) 0.0852(13) Uani 1 1 d . . . . .
H17A H 0.1121 0.1434 0.0940 0.102 Uiso 1 1 calc R U . A 1
H17B H -0.0139 0.0855 0.0432 0.102 Uiso 1 1 calc R U . A 1
O1 O -0.21758(16) 0.08902(8) 0.76985(15) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.11392(18) 0.16467(7) 0.31484(15) 0.0366(4) Uani 1 1 d . . . . .
N1 N -0.33029(18) 0.18886(9) 0.78663(17) 0.0304(4) Uani 1 1 d . . . . .
H1A H -0.3335 0.2362 0.7825 0.036 Uiso 1 1 calc R U . . .
N2 N 0.1496(2) 0.06245(11) 0.22603(16) 0.0453(5) Uani 1 1 d . . . . .
H2A H 0.1826 0.0181 0.2416 0.054 Uiso 1 1 calc R U . . .
Cl1 Cl -0.28047(11) 0.14447(5) 1.07026(8) 0.0727(3) Uani 1 1 d . . . . .
C18A C 0.1501(5) 0.0540(2) 0.0131(4) 0.0315(10) Uani 0.470(3) 1 d . . P B 1
H18A H 0.0892 0.0587 -0.0859 0.038 Uiso 0.470(3) 1 calc R U P B 1
H18B H 0.1686 0.0024 0.0378 0.038 Uiso 0.470(3) 1 calc R U P B 1
Cl2A Cl 0.31095(18) 0.10507(14) 0.07295(16) 0.0630(9) Uani 0.470(3) 1 d . . P B
1
C18B C 0.2302(6) 0.1287(2) 0.0693(4) 0.0351(9) Uani 0.530(3) 1 d . . P B 2
H18C H 0.2968 0.1553 0.1515 0.042 Uiso 0.530(3) 1 calc R U P B 2
H18D H 0.1935 0.1619 -0.0091 0.042 Uiso 0.530(3) 1 calc R U P B 2
Cl2B Cl 0.31503(13) 0.05202(10) 0.04128(11) 0.0468(5) Uani 0.530(3) 1 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'
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C3 S1 S2 103.87(6) . . ?
C11 S2 S1 104.31(6) . . ?
O1 C7 N1 123.47(17) . . ?
O1 C7 C4 120.61(17) . . ?
N1 C7 C4 115.91(16) . . ?
C6 C1 C3 120.39(18) . . ?
C5 C2 C4 121.13(18) . . ?
C1 C3 C4 119.41(16) . . ?
C1 C3 S1 122.25(14) . . ?
C4 C3 S1 118.33(14) . . ?
C2 C4 C3 119.22(17) . . ?
C2 C4 C7 120.05(16) . . ?
C3 C4 C7 120.64(16) . . ?
C2 C5 C6 119.48(18) . . ?
N1 C8 C9 111.66(19) . . ?
C5 C6 C1 120.30(19) . . ?
C8 C9 Cl1 110.95(17) . . ?
C15 C10 C11 120.63(17) . . ?
C10 C11 C12 119.28(17) . . ?
C10 C11 S2 122.64(14) . . ?
C12 C11 S2 118.03(12) . . ?
C13 C12 C11 119.29(15) . . ?
C13 C12 C16 120.59(16) . . ?
C11 C12 C16 120.10(16) . . ?
O2 C16 N2 122.72(17) . . ?
O2 C16 C12 120.30(16) . . ?
N2 C16 C12 116.97(16) . . ?
C14 C13 C12 120.89(17) . . ?
C15 C14 C13 119.66(18) . . ?
C14 C15 C10 120.25(17) . . ?
N2 C17 C18A 110.5(2) . . ?
N2 C17 C18B 108.1(3) . . ?
C7 N1 C8 122.40(17) . . ?
C16 N2 C17 121.6(2) . . ?
C17 C18A Cl2A 97.9(3) . . ?
C17 C18B Cl2B 103.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.7915(18) . ?
S1 S2 2.0414(6) . ?
S2 C11 1.7861(18) . ?
C7 O1 1.239(2) . ?
C7 N1 1.335(3) . ?
C7 C4 1.494(3) . ?
C1 C6 1.390(3) . ?
C1 C3 1.393(3) . ?
C2 C5 1.378(3) . ?
C2 C4 1.399(2) . ?
C3 C4 1.402(2) . ?
C5 C6 1.390(3) . ?
C8 N1 1.447(3) . ?
C8 C9 1.508(3) . ?
C9 Cl1 1.796(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.390(2) . ?
C11 C12 1.408(2) . ?
C12 C13 1.394(3) . ?
C12 C16 1.486(2) . ?
C16 O2 1.235(2) . ?
C16 N2 1.338(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.383(3) . ?
C17 N2 1.452(3) . ?
C17 C18A 1.464(5) . ?
C17 C18B 1.758(7) . ?
C18A Cl2A 1.794(5) . ?
C18B Cl2B 1.795(5) . ?
