#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:00:07 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/82/1568295.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_1568295
loop_
_publ_author_name
'Tang, Chunlin'
'Song, Lijuan'
'Zhou, Kang'
'Ren, Peng'
'Zhao, Engui'
'He, Zikai'
_publ_section_title
;
 Manipulating D-A interaction to achieve stable photoinduced organic
 radicals in triphenylphosphine crystals.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1871
_journal_page_last               1877
_journal_paper_doi               10.1039/d2sc05753k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H16 Cl4 N P'
_chemical_formula_sum            'C20 H16 Cl4 N P'
_chemical_formula_weight         443.11
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d9w4r
_audit_creation_date             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                91.285(2)
_cell_angle_beta                 107.443(2)
_cell_angle_gamma                93.782(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4252(5)
_cell_length_b                   10.4766(6)
_cell_length_c                   10.6229(6)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.80
_cell_measurement_theta_min      4.23
_cell_volume                     997.55(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18386
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.733
_diffrn_reflns_theta_min         4.233
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.179
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0746 after correction.
The Ratio of minimum to maximum transmission is 0.0849.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0521
_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)+(0.1012P)²+0.2047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3798
_reflns_number_total             4036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05753k3.cif
_cod_data_source_block           DCP-DMA
_cod_depositor_comments
'Adding full bibliography for 1568291--1568295.cif.'
_cod_database_code               1568295
_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   0.501
_shelx_estimated_absorpt_t_min   0.371
_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 Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00O(H00B,H00C,H00E), C00P(H00I,H00K,H00N)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
P01 P 0.39432(5) 0.87928(5) 0.18426(5) 0.04168(17) Uani 1 1 d . . . . .
Cl02 Cl 0.14710(7) 0.40532(5) -0.05217(6) 0.05764(19) Uani 1 1 d . . . . .
Cl03 Cl -0.19701(6) 0.93534(6) 0.10977(6) 0.05937(19) Uani 1 1 d . . . . .
Cl04 Cl 0.51392(7) 0.69152(8) -0.25279(6) 0.0687(2) Uani 1 1 d . . . . .
Cl05 Cl 0.12172(7) 0.73142(8) 0.55815(6) 0.0696(2) Uani 1 1 d . . . . .
N006 N 0.8286(2) 0.68494(17) 0.66797(17) 0.0477(4) Uani 1 1 d . . . . .
C007 C 0.2288(2) 0.85015(18) 0.24113(19) 0.0418(4) Uani 1 1 d . . . . .
C008 C 0.0929(2) 0.88989(19) 0.1622(2) 0.0450(4) Uani 1 1 d . . . . .
H008 H 0.085451 0.922781 0.078056 0.054 Uiso 1 1 calc R U . . .
C009 C 0.2687(2) 0.64035(19) 0.04904(19) 0.0446(4) Uani 1 1 d . . . . .
H009 H 0.216561 0.628286 0.112284 0.054 Uiso 1 1 calc R U . . .
C00A C 0.5559(2) 0.6851(2) 0.3369(2) 0.0451(4) Uani 1 1 d . . . . .
H00A H 0.500675 0.624711 0.268899 0.054 Uiso 1 1 calc R U . . .
C00B C 0.5363(2) 0.8153(2) 0.31975(19) 0.0421(4) Uani 1 1 d . . . . .
C00C C 0.7359(2) 0.7280(2) 0.55440(19) 0.0437(4) Uani 1 1 d . . . . .
C00D C 0.7176(2) 0.8594(2) 0.5364(2) 0.0452(4) Uani 1 1 d . . . . .
H00D H 0.771943 0.920272 0.604097 0.054 Uiso 1 1 calc R U . . .
C00E C 0.3595(2) 0.7526(2) 0.05390(19) 0.0434(4) Uani 1 1 d . . . . .
C00F C 0.6211(2) 0.9010(2) 0.4210(2) 0.0446(4) Uani 1 1 d . . . . .
H00F H 0.612640 0.990299 0.410689 0.054 Uiso 1 1 calc R U . . .
C00G C 0.4328(2) 0.7689(2) -0.0416(2) 0.0478(4) Uani 1 1 d . . . . .
H00G H 0.492979 0.845555 -0.040735 0.057 Uiso 1 1 calc R U . . .
C00H C 0.6534(2) 0.6416(2) 0.4501(2) 0.0457(4) Uani 1 1 d . . . . .
H00H H 0.665053 0.552408 0.457726 0.055 Uiso 1 1 calc R U . . .
C00I C 0.2557(2) 0.5472(2) -0.0488(2) 0.0466(4) Uani 1 1 d . . . . .
C00J C 0.2366(2) 0.8008(2) 0.3637(2) 0.0451(4) Uani 1 1 d . . . . .
H00J H 0.327554 0.772784 0.418629 0.054 Uiso 1 1 calc R U . . .
C00K C 0.4176(2) 0.6730(2) -0.1377(2) 0.0515(5) Uani 1 1 d . . . . .
C00L C 0.3284(2) 0.5613(2) -0.1437(2) 0.0510(5) Uani 1 1 d . . . . .
H00L H 0.317377 0.496546 -0.210697 0.061 Uiso 1 1 calc R U . . .
C00M C -0.0256(2) 0.8328(2) 0.3290(2) 0.0499(5) Uani 1 1 d . . . . .
H00M H -0.111164 0.827435 0.358889 0.060 Uiso 1 1 calc R U . . .
C00N C -0.0301(2) 0.8810(2) 0.2074(2) 0.0468(4) Uani 1 1 d . . . . .
C00O C 0.9120(3) 0.7745(2) 0.7750(2) 0.0547(5) Uani 1 1 d . . . . .
H00B H 0.970761 0.838269 0.741444 0.082 Uiso 1 1 calc R U . . .
H00C H 0.979004 0.727960 0.844645 0.082 Uiso 1 1 calc R U . . .
H00E H 0.842579 0.817562 0.811028 0.082 Uiso 1 1 calc R U . . .
C00P C 0.8481(3) 0.5495(2) 0.6815(2) 0.0569(5) Uani 1 1 d . . . . .
H00I H 0.751244 0.502880 0.670787 0.085 Uiso 1 1 calc R U . . .
H00K H 0.916009 0.535432 0.769149 0.085 Uiso 1 1 calc R U . . .
H00N H 0.890086 0.518416 0.613593 0.085 Uiso 1 1 calc R U . . .
C00Q C 0.1092(3) 0.7931(2) 0.4044(2) 0.0498(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C00B P01 C007 100.38(9) . . ?
C00B P01 C00E 102.45(9) . . ?
C00E P01 C007 100.92(9) . . ?
C00C N006 C00O 120.56(18) . . ?
C00C N006 C00P 120.25(18) . . ?
C00P N006 C00O 119.17(18) . . ?
C008 C007 P01 117.95(15) . . ?
C00J C007 P01 122.71(16) . . ?
C00J C007 C008 119.10(19) . . ?
C007 C008 H008 120.2 . . ?
C00N C008 C007 119.64(19) . . ?
C00N C008 H008 120.2 . . ?
C00E C009 H009 120.4 . . ?
C00I C009 H009 120.4 . . ?
C00I C009 C00E 119.29(19) . . ?
C00B C00A H00A 119.1 . . ?
C00H C00A H00A 119.1 . . ?
C00H C00A C00B 121.84(19) . . ?
C00A C00B P01 124.60(15) . . ?
C00F C00B P01 117.73(15) . . ?
C00F C00B C00A 117.31(18) . . ?
N006 C00C C00D 121.79(19) . . ?
N006 C00C C00H 120.99(19) . . ?
C00D C00C C00H 117.22(18) . . ?
C00C C00D H00D 119.6 . . ?
C00F C00D C00C 120.89(19) . . ?
C00F C00D H00D 119.6 . . ?
C009 C00E P01 123.42(15) . . ?
C00G C00E P01 117.33(16) . . ?
C00G C00E C009 119.20(19) . . ?
C00B C00F H00F 119.1 . . ?
C00D C00F C00B 121.80(19) . . ?
C00D C00F H00F 119.1 . . ?
C00E C00G H00G 120.1 . . ?
C00K C00G C00E 119.8(2) . . ?
C00K C00G H00G 120.1 . . ?
C00A C00H C00C 120.89(19) . . ?
C00A C00H H00H 119.6 . . ?
C00C C00H H00H 119.6 . . ?
C009 C00I Cl02 119.39(17) . . ?
C009 C00I C00L 122.3(2) . . ?
C00L C00I Cl02 118.32(17) . . ?
C007 C00J H00J 120.5 . . ?
C00Q C00J C007 119.08(19) . . ?
C00Q C00J H00J 120.5 . . ?
C00G C00K Cl04 119.59(19) . . ?
C00L C00K Cl04 118.76(17) . . ?
C00L C00K C00G 121.6(2) . . ?
C00I C00L H00L 121.1 . . ?
C00K C00L C00I 117.8(2) . . ?
C00K C00L H00L 121.1 . . ?
C00N C00M H00M 121.6 . . ?
C00Q C00M H00M 121.6 . . ?
C00Q C00M C00N 116.8(2) . . ?
C008 C00N Cl03 118.97(17) . . ?
C008 C00N C00M 122.53(19) . . ?
C00M C00N Cl03 118.49(17) . . ?
N006 C00O H00B 109.5 . . ?
N006 C00O H00C 109.5 . . ?
N006 C00O H00E 109.5 . . ?
H00B C00O H00C 109.5 . . ?
H00B C00O H00E 109.5 . . ?
H00C C00O H00E 109.5 . . ?
N006 C00P H00I 109.5 . . ?
N006 C00P H00K 109.5 . . ?
N006 C00P H00N 109.5 . . ?
H00I C00P H00K 109.5 . . ?
H00I C00P H00N 109.5 . . ?
H00K C00P H00N 109.5 . . ?
C00J C00Q Cl05 118.24(17) . . ?
C00M C00Q Cl05 118.87(18) . . ?
C00M C00Q C00J 122.9(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
P01 C007 1.844(2) . ?
P01 C00B 1.822(2) . ?
P01 C00E 1.837(2) . ?
Cl02 C00I 1.741(2) . ?
Cl03 C00N 1.743(2) . ?
Cl04 C00K 1.734(2) . ?
Cl05 C00Q 1.743(2) . ?
N006 C00C 1.366(3) . ?
N006 C00O 1.452(3) . ?
N006 C00P 1.448(3) . ?
C007 C008 1.399(3) . ?
C007 C00J 1.396(3) . ?
C008 H008 0.9500 . ?
C008 C00N 1.380(3) . ?
C009 H009 0.9500 . ?
C009 C00E 1.399(3) . ?
C009 C00I 1.382(3) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.398(3) . ?
C00A C00H 1.384(3) . ?
C00B C00F 1.396(3) . ?
C00C C00D 1.409(3) . ?
C00C C00H 1.414(3) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.388(3) . ?
C00E C00G 1.396(3) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00K 1.386(3) . ?
C00H H00H 0.9500 . ?
C00I C00L 1.384(3) . ?
C00J H00J 0.9500 . ?
C00J C00Q 1.391(3) . ?
C00K C00L 1.384(4) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.388(3) . ?
C00M C00Q 1.380(3) . ?
C00O H00B 0.9800 . ?
C00O H00C 0.9800 . ?
C00O H00E 0.9800 . ?
C00P H00I 0.9800 . ?
C00P H00K 0.9800 . ?
C00P H00N 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
_geom_torsion_publ_flag
P01 C007 C008 C00N -173.80(15) . . . . ?
P01 C007 C00J C00Q 173.92(16) . . . . ?
P01 C00B C00F C00D 171.24(16) . . . . ?
P01 C00E C00G C00K 176.20(16) . . . . ?
Cl02 C00I C00L C00K -178.25(16) . . . . ?
Cl04 C00K C00L C00I 178.33(17) . . . . ?
N006 C00C C00D C00F -179.00(19) . . . . ?
N006 C00C C00H C00A 177.84(19) . . . . ?
C007 P01 C00B C00A 77.91(19) . . . . ?
C007 P01 C00B C00F -94.96(17) . . . . ?
C007 P01 C00E C009 -23.45(18) . . . . ?
C007 P01 C00E C00G 159.00(16) . . . . ?
C007 C008 C00N Cl03 178.15(15) . . . . ?
C007 C008 C00N C00M -0.5(3) . . . . ?
C007 C00J C00Q Cl05 -179.84(16) . . . . ?
C007 C00J C00Q C00M -0.3(3) . . . . ?
C008 C007 C00J C00Q -0.4(3) . . . . ?
C009 C00E C00G C00K -1.5(3) . . . . ?
C009 C00I C00L C00K 0.6(3) . . . . ?
C00A C00B C00F C00D -2.2(3) . . . . ?
C00B P01 C007 C008 178.71(15) . . . . ?
C00B P01 C007 C00J 4.37(19) . . . . ?
C00B P01 C00E C009 79.88(18) . . . . ?
C00B P01 C00E C00G -97.67(17) . . . . ?
C00B C00A C00H C00C 1.0(3) . . . . ?
C00C C00D C00F C00B 1.4(3) . . . . ?
C00D C00C C00H C00A -1.7(3) . . . . ?
C00E P01 C007 C008 -76.30(17) . . . . ?
C00E P01 C007 C00J 109.36(17) . . . . ?
C00E P01 C00B C00A -25.8(2) . . . . ?
C00E P01 C00B C00F 161.29(16) . . . . ?
C00E C009 C00I Cl02 178.14(15) . . . . ?
C00E C009 C00I C00L -0.7(3) . . . . ?
C00E C00G C00K Cl04 -177.86(16) . . . . ?
C00E C00G C00K C00L 1.4(3) . . . . ?
C00G C00K C00L C00I -0.9(3) . . . . ?
C00H C00A C00B P01 -171.94(17) . . . . ?
C00H C00A C00B C00F 1.0(3) . . . . ?
C00H C00C C00D C00F 0.6(3) . . . . ?
C00I C009 C00E P01 -176.40(15) . . . . ?
C00I C009 C00E C00G 1.1(3) . . . . ?
C00J C007 C008 C00N 0.8(3) . . . . ?
C00N C00M C00Q Cl05 -179.93(17) . . . . ?
C00N C00M C00Q C00J 0.5(3) . . . . ?
C00O N006 C00C C00D 0.0(3) . . . . ?
C00O N006 C00C C00H -179.5(2) . . . . ?
C00P N006 C00C C00D -178.2(2) . . . . ?
C00P N006 C00C C00H 2.3(3) . . . . ?
C00Q C00M C00N Cl03 -178.80(17) . . . . ?
C00Q C00M C00N C008 -0.1(3) . . . . ?
