#------------------------------------------------------------------------------
#$Date: 2022-04-20 01:23:03 +0300 (Wed, 20 Apr 2022) $
#$Revision: 274584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566828.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_1566828
loop_
_publ_author_name
'Zhou, Jun'
'Mao, Lijun'
'Wu, Meng-Xiang'
'Peng, Zhiyong'
'Yang, Yiming'
'Zhou, Manfei'
'Zhao, Xiao-Li'
'Shi, Xueliang'
'Yang, Hai-Bo'
_publ_section_title
;
 Extended phenothiazines: synthesis, photophysical and redox properties,
 and efficient photocatalytic oxidative coupling of amines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01086K
_journal_year                    2022
_chemical_formula_moiety         '2(F1.5 Sb0.25), C13 H11.5 N0.5 S0.5'
_chemical_formula_sum            'C13 H11.5 F3 N0.5 S0.5 Sb0.5'
_chemical_formula_weight         308.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 133.036(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.184(5)
_cell_length_b                   6.8384(13)
_cell_length_c                   19.415(4)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.835
_cell_measurement_theta_min      2.871
_cell_volume                     2638.0(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_min         3.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1500 before and 0.0401 after correction. The Ratio of minimum to maximum transmission is 0.8314. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.585
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0590
_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)+(0.1278P)²+0.6385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             3204
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           mo_dm21091_0m
_cod_original_cell_volume        2638.1(9)
_cod_original_formula_sum        'C13 H11.50 F3 N0.50 S0.50 Sb0.50'
_cod_database_code               1566828
_shelx_shelxl_version_number     2017/1
_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   0.943
_shelx_estimated_absorpt_t_min   0.932
_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. Restrained distances
 F6-F4 \\sim F7-F5
 with sigma of 0.02
3. Rigid bond restraints
 Sb2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Sb2, F7, F6, F4, F5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F8, Sb2, F5, F6, F4, F7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
F6 \\sim F5 \\sim F4 \\sim F7 \\sim Sb2: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
F8 \\sim Sb2 \\sim F5 \\sim F6 \\sim F4 \\sim F7: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
Sb2 \\sim F8 \\sim F4 \\sim F6 \\sim F5 \\sim F7: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Fixed Sof: Sb2(0.25) H23A(0.5) H23B(0.5) H23C(0.5) F4(0.25) F7(0.25) F6(0.5)
 F5(0.25) F8(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C8(H8), C2(H2), C13(H13), C5(H5), C10(H10),
 C4(H4), C12(H12), C11(H11), C3(H3)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Sb1 Sb 1.000000 0.500000 0.500000 0.0633(3) Uani 1 4 d S T P . .
Sb2 Sb 0.89124(6) 0.000000 0.92295(7) 0.0907(4) Uani 0.5 2 d S TU P . .
S1 S 0.78797(11) 0.000000 0.59489(12) 0.0713(5) Uani 1 2 d S T P . .
F2 F 0.9217(2) 0.500000 0.4801(4) 0.0962(14) Uani 1 2 d S T P . .
N1 N 0.7954(3) 0.000000 0.4418(3) 0.0527(10) Uani 1 2 d S T P . .
C20 C 0.8032(3) 0.000000 0.2312(3) 0.0471(11) Uani 1 2 d S T P . .
C17 C 0.7989(3) 0.000000 0.3701(4) 0.0494(11) Uani 1 2 d S T P . .
C21 C 0.8024(3) 0.000000 0.1518(4) 0.0591(14) Uani 1 2 d S T P . .
F1 F 0.9470(3) 0.500000 0.3711(4) 0.156(4) Uani 1 2 d S T P . .
C1 C 0.8555(3) 0.000000 0.5355(4) 0.0581(14) Uani 1 2 d S T P . .
C14 C 0.6087(3) 0.000000 0.2764(5) 0.0626(15) Uani 1 2 d S T P . .
C6 C 0.8576(4) 0.000000 0.6109(4) 0.0646(16) Uani 1 2 d S T P . .
C15 C 0.6748(3) 0.000000 0.3132(4) 0.0587(13) Uani 1 2 d S T P . .
H15 H 0.680858 0.000000 0.271496 0.070 Uiso 1 2 calc RS T P . .
C16 C 0.7308(3) 0.000000 0.4085(4) 0.0529(12) Uani 1 2 d S T P . .
C9 C 0.6013(4) 0.000000 0.3436(6) 0.0673(17) Uani 1 2 d S T P . .
C7 C 0.7219(3) 0.000000 0.4731(4) 0.0584(14) Uani 1 2 d S T P . .
C18 C 0.7999(3) 0.1720(6) 0.3359(4) 0.0722(13) Uani 1 1 d . . . . .
H18 H 0.798609 0.289877 0.358475 0.087 Uiso 1 1 calc R . . . .
C19 C 0.8029(3) 0.1718(6) 0.2684(4) 0.0734(13) Uani 1 1 d . . . . .
H19 H 0.804844 0.290549 0.247012 0.088 Uiso 1 1 calc R . . . .
F3 F 1.000000 0.2316(10) 0.500000 0.169(4) Uani 1 2 d S T P . .
C8 C 0.6582(4) 0.000000 0.4395(5) 0.0639(16) Uani 1 2 d S T P . .
H8 H 0.653001 0.000000 0.482117 0.077 Uiso 1 2 calc RS T P . .
C2 C 0.9179(4) 0.000000 0.5575(5) 0.0740(18) Uani 1 2 d S T P . .
H2 H 0.917789 0.000000 0.509492 0.089 Uiso 1 2 calc RS T P . .
C22 C 0.8368(3) 0.1795(9) 0.1554(4) 0.0841(15) Uani 1 1 d . . . . .
H22A H 0.813264 0.294685 0.147716 0.126 Uiso 1 1 calc GR . . . .
H22B H 0.836422 0.172960 0.105659 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.882447 0.184542 0.215094 0.126 Uiso 1 1 calc GR . . . .
C13 C 0.5534(4) 0.000000 0.1813(6) 0.0778(19) Uani 1 2 d S T P . .
H13 H 0.559121 0.000000 0.139322 0.093 Uiso 1 2 calc RS T P . .
C5 C 0.9215(5) 0.000000 0.7048(5) 0.082(2) Uani 1 2 d S T P . .
H5 H 0.923349 0.000000 0.754475 0.099 Uiso 1 2 calc RS T P . .
C23 C 0.7284(4) 0.000000 0.0587(5) 0.105(3) Uani 1 2 d S T P . .
H23A H 0.707249 -0.118842 0.053492 0.157 Uiso 0.5 1 calc GR . . A -1
H23B H 0.725799 0.008965 0.006930 0.157 Uiso 0.5 1 calc GR . . A -1
H23C H 0.705735 0.109877 0.057291 0.157 Uiso 0.5 1 calc GR . . A -1
C10 C 0.5348(5) 0.000000 0.3063(7) 0.081(2) Uani 1 2 d S T P . .
H10 H 0.527928 0.000000 0.347061 0.097 Uiso 1 2 calc RS T P . .
C4 C 0.9789(5) 0.000000 0.7240(6) 0.088(2) Uani 1 2 d S T P . .
H4 H 1.019831 0.000000 0.786343 0.106 Uiso 1 2 calc RS T P . .
C12 C 0.4900(4) 0.000000 0.1476(7) 0.089(2) Uani 1 2 d S T P . .
H12 H 0.452552 0.000000 0.083100 0.107 Uiso 1 2 calc RS T P . .
C11 C 0.4822(5) 0.000000 0.2137(9) 0.097(3) Uani 1 2 d S T P . .
H11 H 0.439046 0.000000 0.191117 0.117 Uiso 1 2 calc RS T P . .
C3 C 0.9778(5) 0.000000 0.6505(5) 0.088(2) Uani 1 2 d S T P . .
H3 H 1.018167 0.000000 0.664979 0.105 Uiso 1 2 calc RS T P . .
F4 F 0.9533(7) 0.000000 0.9048(11) 0.149(4) Uani 0.5 2 d DS TU P . .
F7 F 0.8730(7) 0.000000 0.9943(7) 0.112(2) Uani 0.5 2 d DS TU P . .
F6 F 0.8870(5) -0.2777(16) 0.9218(6) 0.131(2) Uani 0.5 1 d D U . . .
F5 F 0.8452(6) 0.000000 0.8210(6) 0.114(3) Uani 0.5 2 d DS TU P . .
F8 F 0.9621(7) 0.000000 1.0490(8) 0.145(3) Uani 0.5 2 d S TU P . .
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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
F2 Sb1 F2 180.0 5_766 . ?
F1 Sb1 F2 89.7(3) 5_766 5_766 ?
F1 Sb1 F2 90.3(3) . 5_766 ?
F1 Sb1 F2 90.3(3) 5_766 . ?
F1 Sb1 F2 89.7(3) . . ?
F1 Sb1 F1 180.0 5_766 . ?
F3 Sb1 F2 90.000(2) 5_766 . ?
F3 Sb1 F2 90.000(3) 5_766 5_766 ?
F3 Sb1 F2 90.000(1) . 5_766 ?
F3 Sb1 F2 90.000(2) . . ?
F3 Sb1 F1 90.000(2) . . ?
F3 Sb1 F1 90.000(2) 5_766 5_766 ?
F3 Sb1 F1 90.000(1) 5_766 . ?
F3 Sb1 F1 90.000(1) . 5_766 ?
F3 Sb1 F3 180.0 5_766 . ?
F7 Sb2 F4 152.5(6) . . ?
F7 Sb2 F6 87.8(3) . . ?
F7 Sb2 F6 87.8(3) . 6 ?
F7 Sb2 F8 63.1(7) . . ?
F6 Sb2 F4 92.9(3) 6 . ?
F6 Sb2 F4 92.9(3) . . ?
F6 Sb2 F6 173.9(6) 6 . ?
F5 Sb2 F4 78.5(6) . . ?
F5 Sb2 F7 129.0(6) . . ?
F5 Sb2 F6 89.7(3) . 6 ?
F5 Sb2 F6 89.7(3) . . ?
F5 Sb2 F8 167.9(7) . . ?
F8 Sb2 F4 89.4(7) . . ?
F8 Sb2 F6 90.9(3) . . ?
F8 Sb2 F6 90.9(3) . 6 ?
C6 S1 C7 103.8(3) . . ?
C1 N1 C17 117.8(5) . . ?
C1 N1 C16 126.2(4) . . ?
C16 N1 C17 116.0(4) . . ?
C19 C20 C21 121.8(2) 6 . ?
C19 C20 C21 121.8(2) . . ?
C19 C20 C19 116.4(5) 6 . ?
C18 C17 N1 120.2(2) . . ?
C18 C17 N1 120.2(2) 6 . ?
C18 C17 C18 119.7(5) . 6 ?
C20 C21 C23 107.0(5) . . ?
C22 C21 C20 111.7(3) 6 . ?
C22 C21 C20 111.7(3) . . ?
C22 C21 C22 108.2(6) 6 . ?
C22 C21 C23 109.0(4) 6 . ?
C22 C21 C23 109.0(4) . . ?
N1 C1 C6 122.2(6) . . ?
N1 C1 C2 118.9(5) . . ?
C6 C1 C2 118.8(6) . . ?
C15 C14 C9 117.1(6) . . ?
C13 C14 C15 122.1(6) . . ?
C13 C14 C9 120.8(6) . . ?
C1 C6 S1 123.6(6) . . ?
C5 C6 S1 118.0(5) . . ?
C5 C6 C1 118.4(7) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 C14 122.6(5) . . ?
C16 C15 H15 118.7 . . ?
N1 C16 C7 120.3(5) . . ?
C15 C16 N1 120.6(4) . . ?
C15 C16 C7 119.0(6) . . ?
C8 C9 C14 119.7(6) . . ?
C8 C9 C10 123.4(6) . . ?
C10 C9 C14 116.9(7) . . ?
C16 C7 S1 123.8(5) . . ?
C8 C7 S1 116.4(4) . . ?
C8 C7 C16 119.8(6) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C20 C19 H19 119.1 . . ?
C18 C19 C20 121.9(4) . . ?
C18 C19 H19 119.1 . . ?
C9 C8 H8 119.1 . . ?
C7 C8 C9 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(7) . . ?
C3 C2 H2 120.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 120.9(7) . . ?
C12 C13 H13 119.5 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.1(7) . . ?
C4 C5 H5 119.0 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(7) . . ?
C11 C10 H10 119.6 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.3(8) . . ?
C3 C4 H4 119.8 . . ?
C13 C12 H12 120.7 . . ?
C13 C12 C11 118.7(9) . . ?
C11 C12 H12 120.7 . . ?
C10 C11 C12 121.9(7) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C2 C3 C4 121.2(9) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
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
Sb1 F2 1.888(4) . ?
Sb1 F2 1.888(4) 5_766 ?
Sb1 F1 1.849(6) . ?
Sb1 F1 1.849(6) 5_766 ?
Sb1 F3 1.836(7) . ?
Sb1 F3 1.836(7) 5_766 ?
Sb2 F4 1.946(11) . ?
Sb2 F7 1.760(9) . ?
Sb2 F6 1.902(11) . ?
Sb2 F6 1.902(11) 6 ?
Sb2 F5 1.451(9) . ?
Sb2 F8 1.807(11) . ?
S1 C6 1.696(8) . ?
S1 C7 1.738(7) . ?
N1 C17 1.459(6) . ?
N1 C1 1.386(8) . ?
N1 C16 1.398(8) . ?
C20 C21 1.526(7) . ?
C20 C19 1.382(5) . ?
C20 C19 1.382(5) 6 ?
C17 C18 1.360(5) 6 ?
C17 C18 1.360(5) . ?
C21 C22 1.515(6) 6 ?
C21 C22 1.515(6) . ?
C21 C23 1.534(10) . ?
C1 C6 1.425(7) . ?
C1 C2 1.439(11) . ?
C14 C15 1.409(9) . ?
C14 C9 1.449(8) . ?
C14 C13 1.371(11) . ?
C6 C5 1.421(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(9) . ?
C16 C7 1.431(7) . ?
C9 C8 1.389(10) . ?
C9 C10 1.416(10) . ?
C7 C8 1.370(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(5) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.378(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C12 1.362(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.334(13) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.329(14) . ?
C4 H4 0.9300 . ?
C4 C3 1.407(12) . ?
C12 H12 0.9300 . ?
C12 C11 1.437(13) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
