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#$Date: 2023-03-02 09:55:14 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568548.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_1568548
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         'C26 H19 Cl N O2 P S'
_chemical_formula_sum            'C26 H19 Cl N O2 P S'
_chemical_formula_weight         475.90
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6906(3)
_cell_length_b                   14.9491(3)
_cell_length_c                   18.9271(4)
_cell_measurement_reflns_used    10393
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.6030
_cell_measurement_theta_min      2.1530
_cell_volume                     4439.55(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (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 0.925
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45014
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        28.285
_diffrn_reflns_theta_max         30.814
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0476
_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)+(0.0665P)²+2.3409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4422
_reflns_number_total             6442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00308f2.cif
_cod_data_source_block           comp_7a_x3295fin
_cod_database_code               1568548
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
Cl1 Cl 0.83449(4) 0.76813(5) 0.43154(3) 0.04215(17) Uani 1 1 d . . . . .
S1 S 0.80095(3) 0.65323(4) 0.37610(3) 0.03148(14) Uani 1 1 d . . . . .
P1 P 0.66363(3) 0.72277(4) 0.30148(3) 0.02430(13) Uani 1 1 d . . . . .
O1 O 0.74320(11) 0.60912(12) 0.42315(9) 0.0423(4) Uani 1 1 d . . . . .
O2 O 0.88052(11) 0.61214(13) 0.36173(9) 0.0458(5) Uani 1 1 d . . . . .
N1 N 0.76163(11) 0.69178(12) 0.30754(9) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.58532(12) 0.63683(14) 0.31285(11) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.52885(13) 0.66127(14) 0.36286(10) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.54824(13) 0.74918(14) 0.39678(11) 0.0254(4) Uani 1 1 d . . . . .
C4 C 0.50394(14) 0.78963(15) 0.45108(11) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.53325(15) 0.87057(16) 0.47853(12) 0.0330(5) Uani 1 1 d . . . . .
C6 C 0.60347(15) 0.91310(16) 0.45018(12) 0.0333(5) Uani 1 1 d . . . . .
C7 C 0.64677(15) 0.87448(16) 0.39371(12) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.61994(13) 0.79253(14) 0.36889(10) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.65257(13) 0.76767(14) 0.21531(11) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.57918(15) 0.81569(18) 0.19786(13) 0.0364(5) Uani 1 1 d . . . . .
C11 C 0.56587(17) 0.84127(19) 0.12886(13) 0.0401(6) Uani 1 1 d . . . . .
C12 C 0.62419(16) 0.81929(16) 0.07739(12) 0.0360(5) Uani 1 1 d . . . . .
C13 C 0.69709(17) 0.77233(17) 0.09424(13) 0.0387(5) Uani 1 1 d . . . . .
C14 C 0.71155(15) 0.74701(17) 0.16331(12) 0.0330(5) Uani 1 1 d . . . . .
C15 C 0.59110(12) 0.55349(14) 0.27107(11) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.62217(14) 0.47597(16) 0.30168(12) 0.0319(5) Uani 1 1 d . . . . .
C17 C 0.63267(16) 0.39925(16) 0.26177(13) 0.0362(5) Uani 1 1 d . . . . .
C18 C 0.61227(15) 0.39965(17) 0.19053(13) 0.0359(5) Uani 1 1 d . . . . .
C19 C 0.58102(15) 0.47653(17) 0.16012(13) 0.0362(5) Uani 1 1 d . . . . .
C20 C 0.57117(14) 0.55356(16) 0.19923(12) 0.0317(5) Uani 1 1 d . . . . .
C21 C 0.45120(12) 0.61007(14) 0.38071(11) 0.0262(4) Uani 1 1 d . . . . .
C22 C 0.43244(15) 0.58643(16) 0.45006(12) 0.0327(5) Uani 1 1 d . . . . .
C23 C 0.35776(17) 0.54167(17) 0.46583(14) 0.0384(5) Uani 1 1 d . . . . .
C24 C 0.30132(15) 0.52015(17) 0.41310(14) 0.0379(5) Uani 1 1 d . . . . .
C25 C 0.31934(14) 0.54113(17) 0.34376(14) 0.0373(5) Uani 1 1 d . . . . .
C26 C 0.39430(14) 0.58570(16) 0.32717(12) 0.0318(5) Uani 1 1 d . . . . .
H4 H 0.4501(16) 0.7628(17) 0.4679(13) 0.033(6) Uiso 1 1 d . . . . .
H5 H 0.5019(19) 0.8976(19) 0.5144(16) 0.050(8) Uiso 1 1 d . . . . .
H6 H 0.6186(14) 0.9675(18) 0.4670(13) 0.030(6) Uiso 1 1 d . . . . .
H7 H 0.6971(16) 0.9023(18) 0.3779(13) 0.036(7) Uiso 1 1 d . . . . .
H10 H 0.5372(18) 0.8285(19) 0.2331(15) 0.048(8) Uiso 1 1 d . . . . .
H11 H 0.5184(19) 0.874(2) 0.1176(15) 0.053(8) Uiso 1 1 d . . . . .
H12 H 0.6146(18) 0.8407(19) 0.0282(16) 0.050(8) Uiso 1 1 d . . . . .
H13 H 0.743(2) 0.752(2) 0.0585(16) 0.059(9) Uiso 1 1 d . . . . .
H14 H 0.7572(17) 0.7158(18) 0.1760(14) 0.036(7) Uiso 1 1 d . . . . .
H16 H 0.6307(16) 0.4779(17) 0.3514(14) 0.036(7) Uiso 1 1 d . . . . .
H17 H 0.653(2) 0.348(2) 0.2787(19) 0.072(11) Uiso 1 1 d . . . . .
H18 H 0.6169(17) 0.3472(18) 0.1634(14) 0.037(7) Uiso 1 1 d . . . . .
H19 H 0.5681(16) 0.4782(18) 0.1102(14) 0.038(7) Uiso 1 1 d . . . . .
H20 H 0.5505(16) 0.6098(19) 0.1762(14) 0.041(7) Uiso 1 1 d . . . . .
H22 H 0.4719(15) 0.5984(17) 0.4836(14) 0.033(7) Uiso 1 1 d . . . . .
H23 H 0.3486(18) 0.527(2) 0.5112(17) 0.055(9) Uiso 1 1 d . . . . .
H24 H 0.2474(16) 0.4925(19) 0.4220(14) 0.042(7) Uiso 1 1 d . . . . .
H25 H 0.2786(17) 0.5233(19) 0.3072(15) 0.045(8) Uiso 1 1 d . . . . .
H26 H 0.4118(17) 0.6004(18) 0.2791(15) 0.044(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
Cl Cl 0.1484 0.1585 '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'
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 118.50(11) . . ?
O2 S1 N1 110.57(10) . . ?
O1 S1 N1 116.14(10) . . ?
O2 S1 Cl1 103.40(9) . . ?
O1 S1 Cl1 103.11(8) . . ?
N1 S1 Cl1 102.49(8) . . ?
N1 P1 C9 105.54(9) . . ?
N1 P1 C8 118.95(9) . . ?
C9 P1 C8 113.52(10) . . ?
N1 P1 C1 116.12(10) . . ?
C9 P1 C1 108.37(9) . . ?
C8 P1 C1 94.01(10) . . ?
S1 N1 P1 123.19(11) . . ?
C2 C1 C15 130.15(19) . . ?
C2 C1 P1 109.95(16) . . ?
C15 C1 P1 119.89(15) . . ?
C1 C2 C21 124.22(19) . . ?
C1 C2 C3 113.99(18) . . ?
C21 C2 C3 121.68(18) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 127.08(19) . . ?
C8 C3 C2 114.11(18) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 119.6(15) . . ?
C5 C4 H4 120.9(15) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 120.4(18) . . ?
C4 C5 H5 118.2(18) . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 119.1(15) . . ?
C7 C6 H6 121.0(15) . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 122.7(16) . . ?
C6 C7 H7 118.0(16) . . ?
C7 C8 C3 121.9(2) . . ?
C7 C8 P1 130.23(17) . . ?
C3 C8 P1 107.90(15) . . ?
C14 C9 C10 119.8(2) . . ?
C14 C9 P1 120.26(17) . . ?
C10 C9 P1 119.54(17) . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.1(17) . . ?
C9 C10 H10 120.4(17) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 120.2(19) . . ?
C10 C11 H11 119.5(19) . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.0(17) . . ?
C13 C12 H12 120.3(17) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 125.4(18) . . ?
C14 C13 H13 114.9(18) . . ?
C13 C14 C9 120.1(2) . . ?
C13 C14 H14 122.2(17) . . ?
C9 C14 H14 117.7(17) . . ?
C16 C15 C20 119.2(2) . . ?
C16 C15 C1 120.20(19) . . ?
C20 C15 C1 120.46(19) . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 123.3(16) . . ?
C15 C16 H16 116.0(16) . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 124(2) . . ?
C18 C17 H17 116(2) . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 119.7(16) . . ?
C17 C18 H18 120.7(16) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 120.4(16) . . ?
C20 C19 H19 118.7(16) . . ?
C19 C20 C15 119.9(2) . . ?
C19 C20 H20 120.3(15) . . ?
C15 C20 H20 119.8(15) . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C2 121.45(19) . . ?
C26 C21 C2 119.70(19) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 121.6(16) . . ?
C21 C22 H22 117.9(16) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 122.5(19) . . ?
C22 C23 H23 117.3(19) . . ?
C23 C24 C25 120.4(2) . . ?
C23 C24 H24 123.0(16) . . ?
C25 C24 H24 116.5(16) . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 118.5(17) . . ?
C26 C25 H25 121.6(17) . . ?
C25 C26 C21 120.1(2) . . ?
C25 C26 H26 124.0(16) . . ?
C21 C26 H26 115.9(16) . . ?
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
Cl1 S1 2.0803(9) . ?
S1 O2 1.4177(17) . ?
S1 O1 1.4314(16) . ?
S1 N1 1.5482(18) . ?
P1 N1 1.6101(17) . ?
P1 C9 1.772(2) . ?
P1 C8 1.785(2) . ?
P1 C1 1.791(2) . ?
C1 C2 1.347(3) . ?
C1 C15 1.478(3) . ?
C2 C21 1.478(3) . ?
C2 C3 1.494(3) . ?
C3 C4 1.380(3) . ?
C3 C8 1.402(3) . ?
C4 C5 1.395(3) . ?
C4 H4 0.99(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.93(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.91(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.94(3) . ?
C9 C14 1.386(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.96(3) . ?
C11 C12 1.376(4) . ?
C11 H11 0.92(3) . ?
C12 C13 1.379(4) . ?
C12 H12 1.00(3) . ?
C13 C14 1.380(3) . ?
C13 H13 1.04(3) . ?
C14 H14 0.89(3) . ?
C15 C16 1.384(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.383(3) . ?
C16 H16 0.95(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.90(4) . ?
C18 C19 1.376(4) . ?
C18 H18 0.94(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.97(3) . ?
C20 H20 1.00(3) . ?
C21 C22 1.391(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.90(2) . ?
C23 C24 1.372(4) . ?
C23 H23 0.90(3) . ?
C24 C25 1.379(4) . ?
C24 H24 0.96(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.98(3) . ?
C26 H26 0.97(3) . ?
