#------------------------------------------------------------------------------
#$Date: 2023-03-02 09:55:14 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568551.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_1568551
loop_
_publ_author_name
'König, Nils'
'Godínez-Loyola, Yokari'
'Yang, Fangshun'
'Laube, Christian'
'Laue, Michael'
'Lönnecke, Peter'
'Strassert, Cristian A.'
'Hey-Hawkins, Evamarie'
_publ_section_title
;
 Facile modification of phosphole-based aggregation-induced emission
 luminogens with sulfonyl isocyanates
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2267
_journal_page_last               2274
_journal_paper_doi               10.1039/D3SC00308F
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C25 H22 N O2 P S'
_chemical_formula_sum            'C25 H22 N O2 P S'
_chemical_formula_weight         431.46
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                106.562(2)
_cell_angle_beta                 99.860(2)
_cell_angle_gamma                107.702(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8731(3)
_cell_length_b                   10.5634(3)
_cell_length_c                   12.9478(4)
_cell_measurement_reflns_used    11610
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.4820
_cell_measurement_theta_min      2.6120
_cell_volume                     1063.05(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
 or
 DIAMOND Version 4.5.3
 K. Brandenburg, Crystal Impact GbR, Bonn, Germany
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2018-2
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25163
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        30.510
_diffrn_reflns_theta_max         32.558
_diffrn_reflns_theta_min         2.512
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         7081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0376
_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)+(0.0464P)²+0.4254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6052
_reflns_number_total             7081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00308f2.cif
_cod_data_source_block           comp_13_x3515fin
_cod_original_cell_volume        1063.05(6)
_cod_database_code               1568551
_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.
;
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
S1 S 0.43864(3) 0.56092(3) 0.80322(2) 0.01537(7) Uani 1 1 d . . . . .
P1 P 0.43191(3) 0.28864(3) 0.68928(2) 0.01415(7) Uani 1 1 d . . . . .
O1 O 0.41421(11) 0.58744(9) 0.69898(7) 0.02128(18) Uani 1 1 d . . . . .
O2 O 0.35372(11) 0.61521(10) 0.88060(8) 0.02143(18) Uani 1 1 d . . . . .
N1 N 0.39468(12) 0.39839(10) 0.78559(8) 0.01658(18) Uani 1 1 d . . . . .
C1 C 0.62580(14) 0.35914(12) 0.66138(10) 0.0168(2) Uani 1 1 d . . . . .
C2 C 0.63722(15) 0.41153(13) 0.57403(10) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.79073(17) 0.48470(15) 0.56536(12) 0.0245(3) Uani 1 1 d . . . . .
C4 C 0.93337(17) 0.50795(15) 0.64414(12) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.92344(16) 0.45675(15) 0.73171(12) 0.0239(2) Uani 1 1 d . . . . .
C6 C 0.77061(15) 0.38143(14) 0.73994(11) 0.0202(2) Uani 1 1 d . . . . .
C7 C 0.43111(14) 0.14631(12) 0.73944(10) 0.0156(2) Uani 1 1 d . . . . .
C8 C 0.43348(15) 0.01877(13) 0.67002(10) 0.0193(2) Uani 1 1 d . . . . .
C9 C 0.41881(16) -0.09388(13) 0.70810(11) 0.0215(2) Uani 1 1 d . . . . .
C10 C 0.40089(16) -0.07982(13) 0.81498(11) 0.0212(2) Uani 1 1 d . . . . .
C11 C 0.40218(16) 0.04772(14) 0.88469(11) 0.0217(2) Uani 1 1 d . . . . .
C12 C 0.41741(15) 0.16098(13) 0.84743(10) 0.0191(2) Uani 1 1 d . . . . .
C13 C 0.26934(14) 0.21391(12) 0.56002(10) 0.0168(2) Uani 1 1 d . . . . .
C14 C 0.28387(16) 0.13399(14) 0.45854(11) 0.0218(2) Uani 1 1 d . . . . .
C15 C 0.15073(18) 0.07274(15) 0.36253(11) 0.0269(3) Uani 1 1 d . . . . .
C16 C 0.00353(17) 0.09147(16) 0.36753(12) 0.0288(3) Uani 1 1 d . . . . .
C17 C -0.01112(16) 0.17110(16) 0.46794(12) 0.0272(3) Uani 1 1 d . . . . .
C18 C 0.12100(15) 0.23186(14) 0.56437(11) 0.0215(2) Uani 1 1 d . . . . .
C19 C 0.65220(14) 0.64423(12) 0.87328(9) 0.0163(2) Uani 1 1 d . . . . .
C20 C 0.71549(15) 0.61184(14) 0.96442(10) 0.0203(2) Uani 1 1 d . . . . .
C21 C 0.88253(16) 0.67766(15) 1.02017(11) 0.0228(2) Uani 1 1 d . . . . .
C22 C 0.98869(15) 0.77449(14) 0.98630(11) 0.0225(2) Uani 1 1 d . . . . .
C23 C 0.92308(17) 0.80553(15) 0.89531(12) 0.0267(3) Uani 1 1 d . . . . .
C24 C 0.75558(16) 0.74111(14) 0.83852(11) 0.0228(2) Uani 1 1 d . . . . .
C25 C 1.17092(17) 0.84082(18) 1.04409(13) 0.0309(3) Uani 1 1 d . . . . .
H2 H 0.537(2) 0.3996(18) 0.5176(14) 0.022(4) Uiso 1 1 d . . . . .
H3 H 0.800(2) 0.520(2) 0.5060(15) 0.034(5) Uiso 1 1 d . . . . .
H4 H 1.041(2) 0.562(2) 0.6394(16) 0.036(5) Uiso 1 1 d . . . . .
H5 H 1.021(2) 0.477(2) 0.7860(15) 0.035(5) Uiso 1 1 d . . . . .
H6 H 0.763(2) 0.3462(18) 0.8007(14) 0.024(4) Uiso 1 1 d . . . . .
H8 H 0.441(2) 0.0064(18) 0.5918(14) 0.024(4) Uiso 1 1 d . . . . .
H9 H 0.415(2) -0.185(2) 0.6588(15) 0.035(5) Uiso 1 1 d . . . . .
H10 H 0.392(2) -0.1534(18) 0.8410(14) 0.026(4) Uiso 1 1 d . . . . .
H11 H 0.391(2) 0.062(2) 0.9600(15) 0.033(5) Uiso 1 1 d . . . . .
H12 H 0.418(2) 0.2459(19) 0.8959(15) 0.027(4) Uiso 1 1 d . . . . .
H14 H 0.386(2) 0.121(2) 0.4549(15) 0.034(5) Uiso 1 1 d . . . . .
H15 H 0.161(2) 0.016(2) 0.2946(16) 0.032(5) Uiso 1 1 d . . . . .
H16 H -0.084(2) 0.052(2) 0.3026(16) 0.035(5) Uiso 1 1 d . . . . .
H17 H -0.110(2) 0.1850(19) 0.4724(15) 0.029(4) Uiso 1 1 d . . . . .
H18 H 0.113(2) 0.285(2) 0.6323(15) 0.029(4) Uiso 1 1 d . . . . .
H20 H 0.646(2) 0.5441(19) 0.9881(14) 0.026(4) Uiso 1 1 d . . . . .
H21 H 0.924(2) 0.6540(19) 1.0820(14) 0.028(4) Uiso 1 1 d . . . . .
H23 H 0.999(2) 0.874(2) 0.8706(16) 0.041(5) Uiso 1 1 d . . . . .
H24 H 0.711(2) 0.763(2) 0.7783(16) 0.039(5) Uiso 1 1 d . . . . .
H25A H 1.216(2) 0.943(2) 1.0532(17) 0.042(5) Uiso 1 1 d . . . . .
H25B H 1.196(2) 0.837(2) 1.1179(16) 0.034(5) Uiso 1 1 d . . . . .
H25C H 1.228(3) 0.791(3) 0.999(2) 0.058(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 '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'
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'
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
O2 S1 O1 116.10(5) . . ?
O2 S1 N1 107.31(5) . . ?
O1 S1 N1 113.43(5) . . ?
O2 S1 C19 107.05(6) . . ?
O1 S1 C19 107.11(5) . . ?
N1 S1 C19 105.11(5) . . ?
N1 P1 C1 115.11(6) . . ?
N1 P1 C13 111.40(5) . . ?
C1 P1 C13 108.91(5) . . ?
N1 P1 C7 104.52(5) . . ?
C1 P1 C7 109.20(5) . . ?
C13 P1 C7 107.34(5) . . ?
S1 N1 P1 124.37(6) . . ?
C2 C1 C6 119.47(11) . . ?
C2 C1 P1 121.63(9) . . ?
C6 C1 P1 118.18(9) . . ?
C3 C2 C1 120.04(11) . . ?
C3 C2 H2 118.3(9) . . ?
C1 C2 H2 121.6(9) . . ?
C2 C3 C4 120.20(12) . . ?
C2 C3 H3 120.8(11) . . ?
C4 C3 H3 119.0(11) . . ?
C3 C4 C5 120.24(12) . . ?
C3 C4 H4 120.4(11) . . ?
C5 C4 H4 119.4(11) . . ?
C6 C5 C4 119.95(12) . . ?
C6 C5 H5 120.8(11) . . ?
C4 C5 H5 119.2(11) . . ?
C5 C6 C1 120.09(11) . . ?
C5 C6 H6 120.4(10) . . ?
C1 C6 H6 119.5(10) . . ?
C12 C7 C8 119.72(10) . . ?
C12 C7 P1 118.80(9) . . ?
C8 C7 P1 121.36(9) . . ?
C9 C8 C7 120.02(11) . . ?
C9 C8 H8 119.5(10) . . ?
C7 C8 H8 120.4(10) . . ?
C10 C9 C8 119.97(12) . . ?
C10 C9 H9 119.5(11) . . ?
C8 C9 H9 120.4(11) . . ?
C11 C10 C9 119.98(11) . . ?
C11 C10 H10 119.5(11) . . ?
C9 C10 H10 120.5(11) . . ?
C10 C11 C12 120.38(12) . . ?
C10 C11 H11 122.7(11) . . ?
C12 C11 H11 116.9(11) . . ?
C11 C12 C7 119.89(11) . . ?
C11 C12 H12 118.8(10) . . ?
C7 C12 H12 121.3(10) . . ?
C18 C13 C14 119.64(11) . . ?
C18 C13 P1 117.62(9) . . ?
C14 C13 P1 122.66(9) . . ?
C15 C14 C13 119.98(12) . . ?
C15 C14 H14 119.9(11) . . ?
C13 C14 H14 120.1(11) . . ?
C16 C15 C14 120.01(13) . . ?
C16 C15 H15 120.7(11) . . ?
C14 C15 H15 119.3(11) . . ?
C17 C16 C15 120.17(12) . . ?
C17 C16 H16 120.3(12) . . ?
C15 C16 H16 119.5(12) . . ?
C16 C17 C18 120.16(13) . . ?
C16 C17 H17 121.0(11) . . ?
C18 C17 H17 118.9(11) . . ?
C17 C18 C13 120.04(13) . . ?
C17 C18 H18 121.1(11) . . ?
C13 C18 H18 118.9(11) . . ?
C24 C19 C20 120.28(11) . . ?
C24 C19 S1 120.55(9) . . ?
C20 C19 S1 119.17(9) . . ?
C21 C20 C19 119.41(11) . . ?
C21 C20 H20 119.7(10) . . ?
C19 C20 H20 120.9(10) . . ?
C20 C21 C22 121.28(11) . . ?
C20 C21 H21 118.4(11) . . ?
C22 C21 H21 120.3(11) . . ?
C23 C22 C21 118.42(12) . . ?
C23 C22 C25 120.55(12) . . ?
C21 C22 C25 121.00(12) . . ?
C22 C23 C24 121.18(12) . . ?
C22 C23 H23 118.3(12) . . ?
C24 C23 H23 120.5(11) . . ?
C19 C24 C23 119.42(11) . . ?
C19 C24 H24 119.2(12) . . ?
C23 C24 H24 121.4(12) . . ?
C22 C25 H25A 111.1(12) . . ?
C22 C25 H25B 112.4(11) . . ?
H25A C25 H25B 106.6(16) . . ?
C22 C25 H25C 109.6(14) . . ?
H25A C25 H25C 108.7(18) . . ?
H25B C25 H25C 108.4(17) . . ?
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 O2 1.4472(9) . ?
S1 O1 1.4489(9) . ?
S1 N1 1.5782(10) . ?
S1 C19 1.7692(12) . ?
P1 N1 1.5994(10) . ?
P1 C1 1.7977(12) . ?
P1 C13 1.7979(12) . ?
P1 C7 1.7983(11) . ?
C1 C2 1.3991(16) . ?
C1 C6 1.4047(16) . ?
C2 C3 1.3881(17) . ?
C2 H2 1.001(16) . ?
C3 C4 1.389(2) . ?
C3 H3 0.948(18) . ?
C4 C5 1.3931(19) . ?
C4 H4 0.976(19) . ?
C5 C6 1.3874(17) . ?
C5 H5 0.940(19) . ?
C6 H6 0.966(16) . ?
C7 C12 1.3928(16) . ?
C7 C8 1.3989(16) . ?
C8 C9 1.3922(16) . ?
C8 H8 1.000(16) . ?
C9 C10 1.3910(18) . ?
C9 H9 0.976(19) . ?
C10 C11 1.3870(18) . ?
C10 H10 0.919(17) . ?
C11 C12 1.3912(16) . ?
C11 H11 0.970(18) . ?
C12 H12 0.934(18) . ?
C13 C18 1.3938(17) . ?
C13 C14 1.3955(17) . ?
C14 C15 1.3904(18) . ?
C14 H14 0.964(19) . ?
C15 C16 1.388(2) . ?
C15 H15 0.948(19) . ?
C16 C17 1.384(2) . ?
C16 H16 0.930(19) . ?
C17 C18 1.3890(18) . ?
C17 H17 0.943(18) . ?
C18 H18 0.928(18) . ?
C19 C24 1.3872(16) . ?
C19 C20 1.3947(16) . ?
C20 C21 1.3864(18) . ?
C20 H20 0.954(17) . ?
C21 C22 1.3917(18) . ?
C21 H21 0.952(17) . ?
C22 C23 1.3915(18) . ?
C22 C25 1.5044(19) . ?
C23 C24 1.3922(18) . ?
C23 H23 0.99(2) . ?
C24 H24 0.936(19) . ?
C25 H25A 0.99(2) . ?
C25 H25B 0.960(19) . ?
C25 H25C 0.98(2) . ?
