#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:23:47 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289388 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/25/7132549.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_7132549
loop_
_publ_author_name
'Sun, Guangping'
'Li, Menghang'
'Cai, Lijuan'
'Zhu, Jinli'
'Tang, Yanfeng'
'Yao, Yong'
_publ_section_title
;
 Carbazole-based artificial light-harvesting system for photocatalytic
 cross-coupling dehydrogenation reaction.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1412
_journal_page_last               1415
_journal_paper_doi               10.1039/d3cc05405e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H14 N O P S'
_chemical_formula_sum            'C19 H14 N O P S'
_chemical_formula_weight         335.34
_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_creation_date             2023-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-11-02 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                109.339(3)
_cell_angle_beta                 92.044(3)
_cell_angle_gamma                102.717(3)
_cell_formula_units_Z            2
_cell_length_a                   8.385(2)
_cell_length_b                   10.473(3)
_cell_length_c                   10.511(3)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.497
_cell_measurement_theta_min      2.396
_cell_volume                     843.7(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.862
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0399 before and 0.0309 after correction.
The Ratio of minimum to maximum transmission is 0.9383.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0363
_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)+(0.0465P)²+0.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3532
_reflns_number_total             3858
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05405e2.cif
_cod_data_source_block           1a
_cod_depositor_comments          'Adding full bibliography for 7132549.cif.'
_cod_original_cell_volume        843.6(4)
_cod_database_code               7132549
_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.
;
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(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
P001 P 0.38710(4) 0.79370(3) 0.73429(3) 0.02965(10) Uani 1 1 d . . . . .
S002 S 0.25312(5) 0.64809(4) 0.92659(4) 0.04868(12) Uani 1 1 d . . . . .
O003 O 0.32463(13) 0.90357(10) 0.83391(10) 0.0411(2) Uani 1 1 d . . . . .
N004 N 0.39852(18) 0.52693(13) 0.72353(14) 0.0461(3) Uani 1 1 d . . . . .
C005 C 0.60561(16) 0.84102(13) 0.73203(14) 0.0333(3) Uani 1 1 d . . . . .
C006 C 0.29068(16) 0.74361(15) 0.56353(14) 0.0354(3) Uani 1 1 d . . . . .
C007 C 0.34935(16) 0.63914(14) 0.78128(13) 0.0337(3) Uani 1 1 d . . . . .
C008 C 0.69648(19) 0.95326(16) 0.84146(15) 0.0416(3) Uani 1 1 d . . . . .
H008 H 0.6435 1.0031 0.9101 0.050 Uiso 1 1 calc R U . . .
C009 C 0.3601(2) 0.43648(15) 0.79536(17) 0.0459(4) Uani 1 1 d . . . . .
C00A C 0.2810(2) 0.48482(17) 0.90918(17) 0.0470(4) Uani 1 1 d . . . . .
C00B C 0.6838(2) 0.76687(18) 0.6290(2) 0.0547(4) Uani 1 1 d . . . . .
H00B H 0.6232 0.6922 0.5554 0.066 Uiso 1 1 calc R U . . .
C00C C 0.8663(2) 0.9903(2) 0.8476(2) 0.0564(4) Uani 1 1 d . . . . .
H00C H 0.9277 1.0654 0.9205 0.068 Uiso 1 1 calc R U . . .
C00D C 0.2107(3) 0.6094(2) 0.48380(18) 0.0608(5) Uani 1 1 d . . . . .
H00D H 0.2116 0.5357 0.5143 0.073 Uiso 1 1 calc R U . . .
C00E C 0.2891(3) 0.8512(2) 0.51527(19) 0.0596(5) Uani 1 1 d . . . . .
H00E H 0.3428 0.9423 0.5683 0.072 Uiso 1 1 calc R U . . .
C00F C 0.9442(2) 0.9169(2) 0.7468(3) 0.0688(6) Uani 1 1 d . . . . .
H00F H 1.0584 0.9420 0.7519 0.083 Uiso 1 1 calc R U . . .
C00G C 0.3985(3) 0.3066(2) 0.7625(3) 0.0739(6) Uani 1 1 d . . . . .
H00G H 0.4523 0.2732 0.6871 0.089 Uiso 1 1 calc R U . . .
C00H C 0.3543(4) 0.2298(2) 0.8451(3) 0.0865(9) Uani 1 1 d . . . . .
H00H H 0.3781 0.1431 0.8245 0.104 Uiso 1 1 calc R U . . .
C00I C 0.8546(2) 0.8063(2) 0.6380(3) 0.0742(6) Uani 1 1 d . . . . .
H00I H 0.9088 0.7573 0.5698 0.089 Uiso 1 1 calc R U . . .
C00J C 0.2376(3) 0.4046(2) 0.9919(2) 0.0739(6) Uani 1 1 d . . . . .
H00J H 0.1844 0.4364 1.0679 0.089 Uiso 1 1 calc R U . . .
C00K C 0.1283(3) 0.5844(3) 0.3574(2) 0.0838(8) Uani 1 1 d . . . . .
H00K H 0.0730 0.4938 0.3042 0.101 Uiso 1 1 calc R U . . .
C00L C 0.2760(3) 0.2782(3) 0.9573(3) 0.0865(9) Uani 1 1 d . . . . .
H00L H 0.2484 0.2236 1.0110 0.104 Uiso 1 1 calc R U . . .
C00M C 0.2081(3) 0.8243(3) 0.3888(2) 0.0788(7) Uani 1 1 d . . . . .
H00M H 0.2083 0.8971 0.3566 0.095 Uiso 1 1 calc R U . . .
C00N C 0.1276(3) 0.6904(3) 0.3109(2) 0.0787(7) Uani 1 1 d . . . . .
H00N H 0.0725 0.6722 0.2260 0.094 Uiso 1 1 calc R U . . .
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'
P P 0.1023 0.0942 '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
O003 P001 C005 113.32(6) . . ?
O003 P001 C006 113.23(6) . . ?
O003 P001 C007 109.39(7) . . ?
C005 P001 C006 107.90(6) . . ?
C005 P001 C007 104.87(6) . . ?
C006 P001 C007 107.66(6) . . ?
C00A S002 C007 88.39(7) . . ?
C007 N004 C009 109.83(13) . . ?
C008 C005 P001 117.21(11) . . ?
C00B C005 P001 122.26(11) . . ?
C00B C005 C008 120.48(14) . . ?
C00D C006 P001 124.67(12) . . ?
C00D C006 C00E 119.04(15) . . ?
C00E C006 P001 116.13(12) . . ?
S002 C007 P001 116.66(8) . . ?
N004 C007 P001 126.33(11) . . ?
N004 C007 S002 116.77(10) . . ?
C005 C008 H008 120.2 . . ?
C00C C008 C005 119.54(16) . . ?
C00C C008 H008 120.2 . . ?
N004 C009 C00A 115.00(14) . . ?
N004 C009 C00G 124.93(18) . . ?
C00A C009 C00G 120.05(17) . . ?
C009 C00A S002 110.01(11) . . ?
C009 C00A C00J 120.77(19) . . ?
C00J C00A S002 129.21(17) . . ?
C005 C00B H00B 120.6 . . ?
C005 C00B C00I 118.75(17) . . ?
C00I C00B H00B 120.6 . . ?
C008 C00C H00C 119.9 . . ?
C00F C00C C008 120.23(17) . . ?
C00F C00C H00C 119.9 . . ?
C006 C00D H00D 120.1 . . ?
C006 C00D C00K 119.72(19) . . ?
C00K C00D H00D 120.1 . . ?
C006 C00E H00E 119.8 . . ?
C00M C00E C006 120.47(19) . . ?
C00M C00E H00E 119.8 . . ?
C00C C00F H00F 119.8 . . ?
C00C C00F C00I 120.41(17) . . ?
C00I C00F H00F 119.8 . . ?
C009 C00G H00G 121.0 . . ?
C00H C00G C009 118.0(2) . . ?
C00H C00G H00G 121.0 . . ?
C00G C00H H00H 119.2 . . ?
C00L C00H C00G 121.6(2) . . ?
C00L C00H H00H 119.2 . . ?
C00B C00I H00I 119.7 . . ?
C00F C00I C00B 120.60(19) . . ?
C00F C00I H00I 119.7 . . ?
C00A C00J H00J 121.0 . . ?
C00L C00J C00A 118.0(2) . . ?
C00L C00J H00J 121.0 . . ?
C00D C00K H00K 119.6 . . ?
C00N C00K C00D 120.8(2) . . ?
C00N C00K H00K 119.6 . . ?
C00H C00L H00L 119.2 . . ?
C00J C00L C00H 121.59(19) . . ?
C00J C00L H00L 119.2 . . ?
C00E C00M H00M 120.0 . . ?
C00N C00M C00E 119.9(2) . . ?
C00N C00M H00M 120.0 . . ?
C00K C00N C00M 120.01(18) . . ?
C00K C00N H00N 120.0 . . ?
C00M C00N H00N 120.0 . . ?
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
P001 O003 1.4837(10) . ?
P001 C005 1.7927(15) . ?
P001 C006 1.7991(14) . ?
P001 C007 1.8108(14) . ?
S002 C007 1.7375(14) . ?
S002 C00A 1.7274(18) . ?
N004 C007 1.2954(18) . ?
N004 C009 1.3884(19) . ?
C005 C008 1.390(2) . ?
C005 C00B 1.387(2) . ?
C006 C00D 1.376(2) . ?
C006 C00E 1.383(2) . ?
C008 H008 0.9300 . ?
C008 C00C 1.384(2) . ?
C009 C00A 1.389(3) . ?
C009 C00G 1.401(2) . ?
C00A C00J 1.402(2) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.391(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.367(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.391(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.382(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.376(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.375(3) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.373(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00L 1.365(4) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.354(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.370(4) . ?
C00N H00N 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
P001 C005 C008 C00C 177.23(12) . . . . ?
P001 C005 C00B C00I -176.99(16) . . . . ?
P001 C006 C00D C00K 174.48(18) . . . . ?
P001 C006 C00E C00M -175.59(18) . . . . ?
S002 C00A C00J C00L -178.88(15) . . . . ?
O003 P001 C005 C008 15.80(13) . . . . ?
O003 P001 C005 C00B -166.63(13) . . . . ?
O003 P001 C006 C00D -123.95(16) . . . . ?
O003 P001 C006 C00E 51.40(15) . . . . ?
O003 P001 C007 S002 -0.25(10) . . . . ?
O003 P001 C007 N004 -174.39(13) . . . . ?
N004 C009 C00A S002 0.24(18) . . . . ?
N004 C009 C00A C00J -179.02(16) . . . . ?
N004 C009 C00G C00H 178.98(19) . . . . ?
C005 P001 C006 C00D 109.80(16) . . . . ?
C005 P001 C006 C00E -74.85(14) . . . . ?
C005 P001 C007 S002 121.60(8) . . . . ?
C005 P001 C007 N004 -52.55(14) . . . . ?
C005 C008 C00C C00F -0.1(3) . . . . ?
C005 C00B C00I C00F -0.2(3) . . . . ?
C006 P001 C005 C008 142.00(11) . . . . ?
C006 P001 C005 C00B -40.43(15) . . . . ?
C006 P001 C007 S002 -123.67(8) . . . . ?
C006 P001 C007 N004 62.18(15) . . . . ?
C006 C00D C00K C00N 0.9(4) . . . . ?
C006 C00E C00M C00N 0.5(4) . . . . ?
C007 P001 C005 C008 -103.44(11) . . . . ?
C007 P001 C005 C00B 74.13(15) . . . . ?
C007 P001 C006 C00D -2.90(17) . . . . ?
C007 P001 C006 C00E 172.45(13) . . . . ?
C007 S002 C00A C009 -0.14(12) . . . . ?
C007 S002 C00A C00J 179.04(18) . . . . ?
C007 N004 C009 C00A -0.2(2) . . . . ?
C007 N004 C009 C00G -178.72(17) . . . . ?
C008 C005 C00B C00I 0.5(3) . . . . ?
C008 C00C C00F C00I 0.4(3) . . . . ?
C009 N004 C007 P001 174.25(11) . . . . ?
C009 N004 C007 S002 0.11(17) . . . . ?
C009 C00A C00J C00L 0.2(3) . . . . ?
C009 C00G C00H C00L -0.5(4) . . . . ?
C00A S002 C007 P001 -174.70(9) . . . . ?
C00A S002 C007 N004 0.02(13) . . . . ?
C00A C009 C00G C00H 0.6(3) . . . . ?
C00A C00J C00L C00H -0.1(3) . . . . ?
C00B C005 C008 C00C -0.4(2) . . . . ?
C00C C00F C00I C00B -0.3(4) . . . . ?
C00D C006 C00E C00M 0.0(3) . . . . ?
C00D C00K C00N C00M -0.3(4) . . . . ?
C00E C006 C00D C00K -0.7(3) . . . . ?
C00E C00M C00N C00K -0.4(4) . . . . ?
C00G C009 C00A S002 178.81(15) . . . . ?
C00G C009 C00A C00J -0.5(3) . . . . ?
C00G C00H C00L C00J 0.3(4) . . . . ?
