#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:05:44 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254914 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126605.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_7126605
loop_
_publ_author_name
'Schillmöller, Timo'
'Ruth, Paul Niklas'
'Herbst-Irmer, Regine'
'Stalke, Dietmar'
_publ_section_title
;
 Three colour solid-state luminescence from positional isomers of facilely
 modified thiophosphoranyl anthracenes.
;
_journal_issue                   54
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7479
_journal_page_last               7482
_journal_paper_doi               10.1039/d0cc02585b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C26 H19 P S'
_chemical_formula_weight         394.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-27 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.46(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.967(2)
_cell_length_b                   8.892(2)
_cell_length_c                   17.201(3)
_cell_measurement_reflns_used    7352
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.178
_cell_measurement_theta_min      2.462
_cell_volume                     2001.5(8)
_computing_cell_refinement       'SAINT V8.38A'
_computing_data_collection       'APEX2 v2012.2'
_computing_data_reduction        'SAINT V8.38A'
_computing_molecular_graphics    'Mercury CSD 3.3 (Build RC5)'
_computing_publication_material  'Mercury CSD 3.3 (Build RC5)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         1.556
_diffrn_source                   'INCOATEC Microsource'
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0340
_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)+(0.0326P)²+1.4335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3371
_reflns_number_total             4113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02585b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7126605--7126606.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126605
_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_min   0.963
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
P1 P 0.21068(3) 0.27935(5) 0.44926(3) 0.01478(11) Uani 1 1 d . . . . .
C1 C 0.34911(12) 0.28435(18) 0.48436(10) 0.0151(3) Uani 1 1 d . . . . .
S1 S 0.15477(3) 0.08197(5) 0.46053(3) 0.02052(12) Uani 1 1 d . . . . .
C9A C 0.40390(12) 0.19618(18) 0.44278(10) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.40195(13) 0.36377(19) 0.55464(10) 0.0175(4) Uani 1 1 d . . . . .
H2 H 0.365181 0.421834 0.581174 0.021 Uiso 1 1 calc R U . . .
C3 C 0.51039(13) 0.36118(19) 0.58865(10) 0.0188(4) Uani 1 1 d . . . . .
H3 H 0.545315 0.416475 0.637637 0.023 Uiso 1 1 calc R U . . .
C4 C 0.56398(13) 0.27994(19) 0.55127(10) 0.0181(4) Uani 1 1 d . . . . .
H4 H 0.636476 0.278706 0.574694 0.022 Uiso 1 1 calc R U . . .
C10A C 0.52199(13) 0.02829(19) 0.36778(10) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.35619(13) 0.11006(19) 0.37161(10) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.283670 0.107524 0.348871 0.021 Uiso 1 1 calc R U . . .
C10 C 0.56989(13) 0.11168(19) 0.43970(10) 0.0178(4) Uani 1 1 d . . . . .
H10 H 0.642351 0.111019 0.463592 0.021 Uiso 1 1 calc R U . . .
C8 C 0.36378(14) -0.0570(2) 0.25938(11) 0.0226(4) Uani 1 1 d . . . . .
H8 H 0.291302 -0.059120 0.235900 0.027 Uiso 1 1 calc R U . . .
C4A C 0.51386(12) 0.19595(18) 0.47730(10) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.41970(15) -0.1347(2) 0.22223(11) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.385959 -0.189917 0.172944 0.031 Uiso 1 1 calc R U . . .
C5 C 0.57796(14) -0.0558(2) 0.32721(11) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.650508 -0.057056 0.349707 0.027 Uiso 1 1 calc R U . . .
C6 C 0.52818(15) -0.1342(2) 0.25640(11) 0.0259(4) Uani 1 1 d . . . . .
H6 H 0.566356 -0.188954 0.229737 0.031 Uiso 1 1 calc R U . . .
C8A C 0.41225(13) 0.02774(19) 0.33309(10) 0.0176(4) Uani 1 1 d . . . . .
C14 C 0.09635(14) 0.4601(2) 0.18160(11) 0.0251(4) Uani 1 1 d . . . . .
H14 H 0.071733 0.498962 0.126701 0.030 Uiso 1 1 calc R U . . .
C16 C 0.22537(13) 0.4509(2) 0.31734(11) 0.0204(4) Uani 1 1 d . . . . .
H16 H 0.289577 0.483243 0.355211 0.024 Uiso 1 1 calc R U . . .
C15 C 0.19009(14) 0.5065(2) 0.23669(11) 0.0235(4) Uani 1 1 d . . . . .
H15 H 0.230247 0.576129 0.219444 0.028 Uiso 1 1 calc R U . . .
C13 C 0.03822(14) 0.3568(2) 0.20643(11) 0.0247(4) Uani 1 1 d . . . . .
H13 H -0.025976 0.324947 0.168371 0.030 Uiso 1 1 calc R U . . .
C12 C 0.07348(13) 0.3000(2) 0.28656(11) 0.0197(4) Uani 1 1 d . . . . .
H12 H 0.033941 0.228239 0.303091 0.024 Uiso 1 1 calc R U . . .
C17 C 0.17251(12) 0.42453(19) 0.50719(10) 0.0169(3) Uani 1 1 d . . . . .
C18 C 0.18269(13) 0.5772(2) 0.49238(12) 0.0223(4) Uani 1 1 d . . . . .
H18 H 0.211764 0.606861 0.452409 0.027 Uiso 1 1 calc R U . . .
C19 C 0.15055(14) 0.6852(2) 0.53575(12) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.158305 0.788921 0.525981 0.030 Uiso 1 1 calc R U . . .
C20 C 0.10692(13) 0.6421(2) 0.59358(12) 0.0244(4) Uani 1 1 d . . . . .
H20 H 0.084030 0.716343 0.622798 0.029 Uiso 1 1 calc R U . . .
C21 C 0.09684(13) 0.4915(2) 0.60860(11) 0.0227(4) Uani 1 1 d . . . . .
H21 H 0.067300 0.462239 0.648347 0.027 Uiso 1 1 calc R U . . .
C22 C 0.12973(13) 0.3825(2) 0.56579(10) 0.0201(4) Uani 1 1 d . . . . .
H22 H 0.122989 0.279041 0.576572 0.024 Uiso 1 1 calc R U . . .
C11 C 0.16715(12) 0.34828(19) 0.34292(10) 0.0166(3) 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 0.0033 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'
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
C1 P1 C11 105.61(9) . . ?
C1 P1 C17 106.41(8) . . ?
C11 P1 C17 104.62(8) . . ?
C1 P1 S1 113.87(6) . . ?
C11 P1 S1 113.37(6) . . ?
C17 P1 S1 112.22(6) . . ?
C2 C1 C9A 120.00(15) . . ?
C2 C1 P1 119.25(13) . . ?
C9A C1 P1 120.57(12) . . ?
C9 C9A C4A 118.22(15) . . ?
C9 C9A C1 123.81(15) . . ?
C4A C9A C1 117.96(15) . . ?
C1 C2 C3 121.49(16) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.01(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C4A 121.43(16) . . ?
C3 C4 H4 119.3 . . ?
C4A C4 H4 119.3 . . ?
C10 C10A C5 122.45(16) . . ?
C10 C10A C8A 118.74(16) . . ?
C5 C10A C8A 118.81(16) . . ?
C8A C9 C9A 121.82(16) . . ?
C8A C9 H9 119.1 . . ?
C9A C9 H9 119.1 . . ?
C4A C10 C10A 121.56(16) . . ?
C4A C10 H10 119.2 . . ?
C10A C10 H10 119.2 . . ?
C7 C8 C8A 120.99(18) . . ?
C7 C8 H8 119.5 . . ?
C8A C8 H8 119.5 . . ?
C10 C4A C4 120.91(15) . . ?
C10 C4A C9A 119.99(15) . . ?
C4 C4A C9A 119.08(15) . . ?
C8 C7 C6 120.62(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C5 C10A 120.59(17) . . ?
C6 C5 H5 119.7 . . ?
C10A C5 H5 119.7 . . ?
C5 C6 C7 120.52(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C9 C8A C8 121.88(16) . . ?
C9 C8A C10A 119.64(15) . . ?
C8 C8A C10A 118.47(16) . . ?
C15 C14 C13 120.11(17) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C16 C11 120.38(17) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C15 C16 119.86(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C12 C13 C14 120.28(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C12 C11 119.94(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C22 C17 C18 119.33(16) . . ?
C22 C17 P1 119.25(13) . . ?
C18 C17 P1 121.39(13) . . ?
C19 C18 C17 120.22(17) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.01(17) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.02(17) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.22(17) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.18(17) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C16 C11 C12 119.43(16) . . ?
C16 C11 P1 120.77(13) . . ?
C12 C11 P1 119.79(13) . . ?
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
P1 C1 1.8135(17) . ?
P1 C11 1.8203(18) . ?
P1 C17 1.8208(18) . ?
P1 S1 1.9579(7) . ?
C1 C2 1.371(2) . ?
C1 C9A 1.447(2) . ?
C9A C9 1.400(2) . ?
C9A C4A 1.440(2) . ?
C2 C3 1.420(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.353(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.430(2) . ?
C4 H4 0.9500 . ?
C10A C10 1.396(2) . ?
C10A C5 1.428(2) . ?
C10A C8A 1.437(2) . ?
C9 C8A 1.397(2) . ?
C9 H9 0.9500 . ?
C10 C4A 1.395(2) . ?
C10 H10 0.9500 . ?
C8 C7 1.358(3) . ?
C8 C8A 1.426(2) . ?
C8 H8 0.9500 . ?
C7 C6 1.421(3) . ?
C7 H7 0.9500 . ?
C5 C6 1.364(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C13 1.388(3) . ?
C14 H14 0.9500 . ?
C16 C15 1.390(2) . ?
C16 C11 1.392(2) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C13 C12 1.387(3) . ?
C13 H13 0.9500 . ?
C12 C11 1.396(2) . ?
C12 H12 0.9500 . ?
C17 C22 1.390(2) . ?
C17 C18 1.397(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
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
C11 P1 C1 C2 123.90(14) . . . . ?
C17 P1 C1 C2 13.08(16) . . . . ?
S1 P1 C1 C2 -111.08(13) . . . . ?
C11 P1 C1 C9A -60.97(15) . . . . ?
C17 P1 C1 C9A -171.79(13) . . . . ?
S1 P1 C1 C9A 64.06(14) . . . . ?
C2 C1 C9A C9 178.99(16) . . . . ?
P1 C1 C9A C9 3.9(2) . . . . ?
C2 C1 C9A C4A -0.3(2) . . . . ?
P1 C1 C9A C4A -175.41(12) . . . . ?
C9A C1 C2 C3 -0.5(2) . . . . ?
P1 C1 C2 C3 174.71(13) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C4A 0.3(3) . . . . ?
C4A C9A C9 C8A -1.3(2) . . . . ?
C1 C9A C9 C8A 179.40(15) . . . . ?
C5 C10A C10 C4A 178.45(15) . . . . ?
C8A C10A C10 C4A -1.2(2) . . . . ?
C10A C10 C4A C4 179.56(15) . . . . ?
C10A C10 C4A C9A 1.1(2) . . . . ?
C3 C4 C4A C10 -179.49(16) . . . . ?
C3 C4 C4A C9A -1.0(2) . . . . ?
C9 C9A C4A C10 0.2(2) . . . . ?
C1 C9A C4A C10 179.51(15) . . . . ?
C9 C9A C4A C4 -178.32(15) . . . . ?
C1 C9A C4A C4 1.0(2) . . . . ?
C8A C8 C7 C6 0.4(3) . . . . ?
C10 C10A C5 C6 -179.15(17) . . . . ?
C8A C10A C5 C6 0.5(2) . . . . ?
C10A C5 C6 C7 -0.6(3) . . . . ?
C8 C7 C6 C5 0.1(3) . . . . ?
C9A C9 C8A C8 -178.38(16) . . . . ?
C9A C9 C8A C10A 1.2(2) . . . . ?
C7 C8 C8A C9 179.11(17) . . . . ?
C7 C8 C8A C10A -0.5(3) . . . . ?
C10 C10A C8A C9 0.1(2) . . . . ?
C5 C10A C8A C9 -179.59(15) . . . . ?
C10 C10A C8A C8 179.67(15) . . . . ?
C5 C10A C8A C8 0.0(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C11 C16 C15 C14 0.3(3) . . . . ?
C15 C14 C13 C12 0.2(3) . . . . ?
C14 C13 C12 C11 0.9(3) . . . . ?
C1 P1 C17 C22 -111.41(14) . . . . ?
C11 P1 C17 C22 137.09(14) . . . . ?
S1 P1 C17 C22 13.77(15) . . . . ?
C1 P1 C17 C18 70.39(16) . . . . ?
C11 P1 C17 C18 -41.12(16) . . . . ?
S1 P1 C17 C18 -164.44(13) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
P1 C17 C18 C19 178.27(14) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
P1 C17 C22 C21 -177.77(13) . . . . ?
C15 C16 C11 C12 0.8(3) . . . . ?
C15 C16 C11 P1 -178.04(13) . . . . ?
C13 C12 C11 C16 -1.4(3) . . . . ?
C13 C12 C11 P1 177.45(13) . . . . ?
C1 P1 C11 C16 -29.40(16) . . . . ?
C17 P1 C11 C16 82.68(15) . . . . ?
S1 P1 C11 C16 -154.74(12) . . . . ?
C1 P1 C11 C12 151.75(14) . . . . ?
C17 P1 C11 C12 -96.16(15) . . . . ?
S1 P1 C11 C12 26.41(15) . . . . ?
