#------------------------------------------------------------------------------
#$Date: 2020-12-23 00:23:46 +0200 (Wed, 23 Dec 2020) $
#$Revision: 260083 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/83/4518337.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_4518337
loop_
_publ_author_name
'He, Jian'
'Bai, Zhi-Qin'
'Yuan, Pan-Feng'
'Wu, Li-Zhu'
'Liu, Qiang'
_publ_section_title
;
 Highly Efficient Iridium-Based Photosensitizers for
 Thia-Paternò--Büchi Reaction and Aza-Photocyclization
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              446
_journal_page_last               455
_journal_paper_doi               10.1021/acscatal.0c05005
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 N O3 S2'
_chemical_formula_sum            'C18 H15 N O3 S2'
_chemical_formula_weight         357.43
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.602(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5004(6)
_cell_length_b                   9.9404(5)
_cell_length_c                   16.6691(10)
_cell_measurement_reflns_used    1445
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      26.0650
_cell_measurement_theta_min      4.1020
_cell_volume                     1667.36(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.75(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -30.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0404292000
_diffrn_orient_matrix_UB_12      0.0011881000
_diffrn_orient_matrix_UB_13      0.0421176000
_diffrn_orient_matrix_UB_21      -0.0157487000
_diffrn_orient_matrix_UB_22      0.0688563000
_diffrn_orient_matrix_UB_23      0.0029943000
_diffrn_orient_matrix_UB_31      -0.0555717000
_diffrn_orient_matrix_UB_32      -0.0186979000
_diffrn_orient_matrix_UB_33      0.0137000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6668
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.377
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0460
_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)+(0.0412P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2314
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c05005_si_002.cif
_cod_data_source_block           hej_1108
_cod_original_cell_volume        1667.35(17)
_cod_database_code               4518337
_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_max   0.961
_shelx_estimated_absorpt_t_min   0.945
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2018-11-08
_olex2_submission_special_instructions 'No special instructions were received'
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 0.43427(6) 0.42616(7) 0.08416(4) 0.0418(2) Uani 1 1 d . . . . .
S2 S 0.42306(7) 0.55642(7) 0.24103(4) 0.0480(2) Uani 1 1 d . . . . .
O1 O 0.20443(15) 0.53034(17) 0.09987(12) 0.0458(5) Uani 1 1 d . . . . .
N2 N 0.45119(17) 0.19365(19) 0.24622(12) 0.0345(5) Uani 1 1 d . . . . .
O3 O 0.28164(16) 0.14033(18) 0.12907(12) 0.0496(5) Uani 1 1 d . . . . .
O4 O 0.58727(17) 0.30005(18) 0.36189(11) 0.0480(5) Uani 1 1 d . . . . .
C5 C 0.3322(2) 0.2180(3) 0.18403(16) 0.0357(6) Uani 1 1 d . . . . .
C6 C 0.4867(2) 0.2971(2) 0.30530(15) 0.0365(6) Uani 1 1 d . . . . .
C7 C 0.5323(2) 0.0777(2) 0.24480(15) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.3231(2) 0.4686(2) 0.14558(15) 0.0366(6) Uani 1 1 d . . . . .
C9 C 0.3767(2) 0.4012(3) 0.28349(15) 0.0412(6) Uani 1 1 d . . . . .
H9 H 0.331731 0.414677 0.326950 0.049 Uiso 1 1 calc R . . . .
C10 C 0.2026(2) 0.6550(2) 0.06129(15) 0.0364(6) Uani 1 1 d . . . . .
C11 C 0.0783(2) 0.6943(3) 0.01410(15) 0.0395(6) Uani 1 1 d . . . . .
H11 H 0.005946 0.637287 0.007930 0.047 Uiso 1 1 calc R . . . .
C12 C 0.2852(2) 0.3557(2) 0.19936(15) 0.0367(6) Uani 1 1 d . . . . .
H12 H 0.191089 0.357524 0.197431 0.044 Uiso 1 1 calc R . . . .
C13 C 0.1680(3) 0.9026(3) -0.01556(17) 0.0504(7) Uani 1 1 d . . . . .
H13 H 0.156394 0.986859 -0.040896 0.061 Uiso 1 1 calc R . . . .
C14 C 0.0616(3) 0.8186(3) -0.02403(16) 0.0473(7) Uani 1 1 d . . . . .
H14 H -0.022541 0.845586 -0.055739 0.057 Uiso 1 1 calc R . . . .
C15 C 0.5598(2) -0.0126(3) 0.30930(17) 0.0443(6) Uani 1 1 d . . . . .
H15 H 0.527588 0.001044 0.355146 0.053 Uiso 1 1 calc R . . . .
C16 C 0.3112(2) 0.7371(3) 0.07037(17) 0.0454(7) Uani 1 1 d . . . . .
H16 H 0.395201 0.710118 0.102263 0.054 Uiso 1 1 calc R . . . .
C17 C 0.5803(2) 0.0596(3) 0.17671(17) 0.0479(7) Uani 1 1 d . . . . .
H17 H 0.561456 0.121939 0.133323 0.057 Uiso 1 1 calc R . . . .
C18 C 0.6833(3) -0.1440(3) 0.2378(2) 0.0612(8) Uani 1 1 d . . . . .
H18 H 0.733679 -0.220006 0.235258 0.073 Uiso 1 1 calc R . . . .
C19 C 0.2921(3) 0.8613(3) 0.03071(17) 0.0503(7) Uani 1 1 d . . . . .
H19 H 0.364646 0.917552 0.035541 0.060 Uiso 1 1 calc R . . . .
C20 C 0.6361(3) -0.1243(3) 0.30556(19) 0.0567(8) Uani 1 1 d . . . . .
H20 H 0.655588 -0.186276 0.349155 0.068 Uiso 1 1 calc R . . . .
C21 C 0.3228(3) 0.3578(3) -0.00962(17) 0.0658(9) Uani 1 1 d . . . . .
H21A H 0.371819 0.334960 -0.048310 0.099 Uiso 1 1 calc GR . . . .
H21B H 0.256206 0.423415 -0.034603 0.099 Uiso 1 1 calc GR . . . .
H21C H 0.280976 0.278591 0.003951 0.099 Uiso 1 1 calc GR . . . .
C22 C 0.6565(3) -0.0523(3) 0.17381(19) 0.0581(8) Uani 1 1 d . . . . .
H22 H 0.689770 -0.065450 0.128343 0.070 Uiso 1 1 calc R . . . .
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'
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
C21 S1 C8 102.45(12) . . ?
C9 S2 C8 77.65(11) . . ?
C10 O1 C8 122.19(17) . . ?
C5 N2 C6 113.40(19) . . ?
C5 N2 C7 122.32(19) . . ?
C6 N2 C7 124.12(19) . . ?
N2 C5 C12 107.4(2) . . ?
O3 C5 N2 124.2(2) . . ?
O3 C5 C12 128.4(2) . . ?
N2 C6 C9 107.5(2) . . ?
O4 C6 N2 124.7(2) . . ?
O4 C6 C9 127.7(2) . . ?
C15 C7 N2 120.5(2) . . ?
C15 C7 C17 121.1(2) . . ?
C17 C7 N2 118.4(2) . . ?
S1 C8 S2 107.26(11) . . ?
O1 C8 S1 114.29(17) . . ?
O1 C8 S2 117.21(17) . . ?
O1 C8 C12 107.15(17) . . ?
C12 C8 S1 118.02(16) . . ?
C12 C8 S2 91.17(15) . . ?
S2 C9 H9 114.3 . . ?
C6 C9 S2 113.65(16) . . ?
C6 C9 H9 114.3 . . ?
C6 C9 C12 104.7(2) . . ?
C12 C9 S2 93.56(15) . . ?
C12 C9 H9 114.3 . . ?
C11 C10 O1 113.7(2) . . ?
C11 C10 C16 121.1(2) . . ?
C16 C10 O1 125.1(2) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C14 119.6(2) . . ?
C14 C11 H11 120.2 . . ?
C5 C12 C8 114.13(19) . . ?
C5 C12 C9 106.03(19) . . ?
C5 C12 H12 112.9 . . ?
C8 C12 H12 112.9 . . ?
C9 C12 C8 96.79(18) . . ?
C9 C12 H12 112.9 . . ?
C14 C13 H13 120.3 . . ?
C14 C13 C19 119.4(3) . . ?
C19 C13 H13 120.3 . . ?
C11 C14 H14 119.8 . . ?
C13 C14 C11 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C7 C15 H15 120.4 . . ?
C7 C15 C20 119.2(2) . . ?
C20 C15 H15 120.4 . . ?
C10 C16 H16 120.9 . . ?
C10 C16 C19 118.2(2) . . ?
C19 C16 H16 120.9 . . ?
C7 C17 H17 120.4 . . ?
C22 C17 C7 119.1(2) . . ?
C22 C17 H17 120.4 . . ?
C20 C18 H18 119.9 . . ?
C22 C18 H18 119.9 . . ?
C22 C18 C20 120.3(3) . . ?
C13 C19 C16 121.2(2) . . ?
C13 C19 H19 119.4 . . ?
C16 C19 H19 119.4 . . ?
C15 C20 H20 119.9 . . ?
C18 C20 C15 120.2(3) . . ?
C18 C20 H20 119.9 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22 119.9 . . ?
C18 C22 C17 120.1(3) . . ?
C18 C22 H22 119.9 . . ?
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 C8 1.809(2) . ?
S1 C21 1.797(3) . ?
S2 C8 1.855(3) . ?
S2 C9 1.821(3) . ?
O1 C8 1.403(3) . ?
O1 C10 1.394(3) . ?
N2 C5 1.398(3) . ?
N2 C6 1.399(3) . ?
N2 C7 1.437(3) . ?
O3 C5 1.200(3) . ?
O4 C6 1.198(3) . ?
C5 C12 1.502(3) . ?
C6 C9 1.516(3) . ?
C7 C15 1.367(3) . ?
C7 C17 1.379(3) . ?
C8 C12 1.557(3) . ?
C9 H9 0.9800 . ?
C9 C12 1.525(3) . ?
C10 C11 1.374(3) . ?
C10 C16 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C14 1.377(3) . ?
C12 H12 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.370(4) . ?
C13 C19 1.374(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C20 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C19 1.387(4) . ?
C17 H17 0.9300 . ?
C17 C22 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C20 1.371(4) . ?
C18 C22 1.370(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C8 C12 C5 -8.1(3) . . . . ?
S1 C8 C12 C9 102.91(19) . . . . ?
S2 C8 C12 C5 -118.37(18) . . . . ?
S2 C8 C12 C9 -7.40(16) . . . . ?
S2 C9 C12 C5 125.10(16) . . . . ?
S2 C9 C12 C8 7.55(16) . . . . ?
O1 C8 C12 C5 122.6(2) . . . . ?
O1 C8 C12 C9 -126.41(19) . . . . ?
O1 C10 C11 C14 176.8(2) . . . . ?
O1 C10 C16 C19 -177.1(2) . . . . ?
N2 C5 C12 C8 97.1(2) . . . . ?
N2 C5 C12 C9 -8.1(2) . . . . ?
N2 C6 C9 S2 -108.39(19) . . . . ?
N2 C6 C9 C12 -7.7(2) . . . . ?
N2 C7 C15 C20 178.9(2) . . . . ?
N2 C7 C17 C22 -179.0(2) . . . . ?
O3 C5 C12 C8 -82.0(3) . . . . ?
O3 C5 C12 C9 172.7(2) . . . . ?
O4 C6 C9 S2 71.2(3) . . . . ?
O4 C6 C9 C12 171.9(2) . . . . ?
C5 N2 C6 O4 -176.7(2) . . . . ?
C5 N2 C6 C9 2.9(2) . . . . ?
C5 N2 C7 C15 -120.5(3) . . . . ?
C5 N2 C7 C17 59.0(3) . . . . ?
C6 N2 C5 O3 -177.4(2) . . . . ?
C6 N2 C5 C12 3.4(2) . . . . ?
C6 N2 C7 C15 64.3(3) . . . . ?
C6 N2 C7 C17 -116.2(3) . . . . ?
C6 C9 C12 C5 9.5(2) . . . . ?
C6 C9 C12 C8 -108.04(19) . . . . ?
C7 N2 C5 O3 6.9(3) . . . . ?
C7 N2 C5 C12 -172.27(19) . . . . ?
C7 N2 C6 O4 -1.2(4) . . . . ?
C7 N2 C6 C9 178.44(19) . . . . ?
C7 C15 C20 C18 -0.1(4) . . . . ?
C7 C17 C22 C18 0.3(4) . . . . ?
C8 S2 C9 C6 101.34(19) . . . . ?
C8 S2 C9 C12 -6.44(13) . . . . ?
C8 O1 C10 C11 175.2(2) . . . . ?
C8 O1 C10 C16 -7.3(4) . . . . ?
C9 S2 C8 S1 -113.60(14) . . . . ?
C9 S2 C8 O1 116.29(18) . . . . ?
C9 S2 C8 C12 6.29(13) . . . . ?
C10 O1 C8 S1 -63.3(3) . . . . ?
C10 O1 C8 S2 63.4(3) . . . . ?
C10 O1 C8 C12 164.0(2) . . . . ?
C10 C11 C14 C13 0.4(4) . . . . ?
C10 C16 C19 C13 0.9(4) . . . . ?
C11 C10 C16 C19 0.2(4) . . . . ?
C14 C13 C19 C16 -1.3(4) . . . . ?
C15 C7 C17 C22 0.4(4) . . . . ?
C16 C10 C11 C14 -0.8(4) . . . . ?
C17 C7 C15 C20 -0.5(4) . . . . ?
C19 C13 C14 C11 0.6(4) . . . . ?
C20 C18 C22 C17 -0.9(5) . . . . ?
C21 S1 C8 S2 -174.59(14) . . . . ?
C21 S1 C8 O1 -42.9(2) . . . . ?
C21 S1 C8 C12 84.5(2) . . . . ?
C22 C18 C20 C15 0.8(5) . . . . ?
