#------------------------------------------------------------------------------
#$Date: 2021-08-04 14:09:36 +0300 (Wed, 04 Aug 2021) $
#$Revision: 267936 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564319.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_1564319
loop_
_publ_author_name
'Xu, Zhen'
'Climent, Clàudia'
'Brown, Christopher M.'
'Hean, Duane'
'Bardeen, Christopher J.'
'Casanova, David'
'Wolf, Michael O.'
_publ_section_title
;
 Controlling ultralong room temperature phosphorescence in organic
 compounds with sulfur oxidation state.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              188
_journal_page_last               195
_journal_paper_doi               10.1039/d0sc04715e
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C36 H24 N2 O1.03 S'
_chemical_formula_sum            'C36 H24 N2 O1.03 S'
_chemical_formula_weight         533.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-20 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.911(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.117(6)
_cell_length_b                   5.3771(12)
_cell_length_c                   20.697(5)
_cell_measurement_reflns_used    6120
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.525
_cell_measurement_theta_min      2.530
_cell_volume                     2521.4(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         1.798
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0744 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.8683. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             1113
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0485
_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)+(0.0406P)²+3.9258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2392
_reflns_number_total             3137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04715e2.cif
_cod_data_source_block           mw330_a
_cod_database_code               1564319
_shelx_shelxl_version_number     2017/1
_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   0.985
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S1 S 0.500000 -0.22098(11) 0.250000 0.01888(17) Uani 1 2 d S T P . .
O1 O 0.45410(12) -0.3300(5) 0.25944(16) 0.0231(9) Uani 0.514(5) 1 d . . . . .
N1 N 0.64656(7) 0.4344(3) 0.54872(9) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.69960(8) 0.5467(3) 0.57581(11) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.73727(8) 0.4809(3) 0.55910(12) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.728315 0.349063 0.523812 0.026 Uiso 1 1 calc R . . . .
C3 C 0.78858(9) 0.6172(4) 0.59646(12) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.814607 0.575373 0.586466 0.028 Uiso 1 1 calc R . . . .
C4 C 0.80192(9) 0.8172(3) 0.64908(12) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.836086 0.909252 0.672328 0.027 Uiso 1 1 calc R . . . .
C5 C 0.76491(8) 0.8790(3) 0.66677(11) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.774017 1.011343 0.701974 0.025 Uiso 1 1 calc R . . . .
C6 C 0.71356(8) 0.7401(3) 0.63111(11) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.66821(8) 0.7437(3) 0.63978(11) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.65843(9) 0.8949(3) 0.68493(11) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.685068 1.019902 0.719129 0.024 Uiso 1 1 calc R . . . .
C9 C 0.60882(9) 0.8563(3) 0.67810(12) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.601681 0.957092 0.707455 0.027 Uiso 1 1 calc R . . . .
C10 C 0.56907(9) 0.6667(3) 0.62739(12) 0.0209(4) Uani 1 1 d . . . . .
H10 H 0.536015 0.642401 0.624075 0.025 Uiso 1 1 calc R . . . .
C11 C 0.57774(8) 0.5137(3) 0.58186(11) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.550995 0.388609 0.547986 0.022 Uiso 1 1 calc R . . . .
C12 C 0.62768(8) 0.5539(3) 0.58863(11) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.61085(8) 0.2827(3) 0.47693(11) 0.0153(4) Uani 1 1 d . . . . .
C14 C 0.57948(8) 0.0828(3) 0.47484(11) 0.0164(4) Uani 1 1 d . . . . .
H14 H 0.582083 0.046335 0.520963 0.020 Uiso 1 1 calc R . . . .
C15 C 0.54440(8) -0.0614(3) 0.40378(11) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.523251 -0.194350 0.402134 0.019 Uiso 1 1 calc R . . . .
C16 C 0.54075(8) -0.0080(3) 0.33504(11) 0.0156(4) Uani 1 1 d . . . . .
C17 C 0.57195(8) 0.1909(3) 0.33680(11) 0.0162(4) Uani 1 1 d . . . . .
H17 H 0.569645 0.225552 0.290812 0.019 Uiso 1 1 calc R . . . .
C18 C 0.60642(8) 0.3372(3) 0.40715(11) 0.0161(4) Uani 1 1 d . . . . .
H18 H 0.626751 0.472371 0.408075 0.019 Uiso 1 1 calc R . . . .
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'
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
O1 S1 O1 136.45(19) 2_655 . ?
O1 S1 C16 105.64(11) . 2_655 ?
O1 S1 C16 101.88(11) . . ?
O1 S1 C16 101.88(11) 2_655 2_655 ?
O1 S1 C16 105.64(11) 2_655 . ?
C16 S1 C16 100.29(11) 2_655 . ?
C1 N1 C13 124.30(15) . . ?
C12 N1 C1 107.88(14) . . ?
C12 N1 C13 125.41(15) . . ?
C2 C1 N1 129.33(16) . . ?
C2 C1 C6 121.50(17) . . ?
C6 C1 N1 109.04(15) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.08(18) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.05(18) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.67(18) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.11(18) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.03(16) . . ?
C5 C6 C1 119.49(17) . . ?
C5 C6 C7 133.46(17) . . ?
C8 C7 C6 132.82(17) . . ?
C8 C7 C12 119.87(17) . . ?
C12 C7 C6 107.29(15) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.06(17) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.52(17) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.58(18) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.73(17) . . ?
C12 C11 H11 121.1 . . ?
N1 C12 C7 108.74(16) . . ?
C11 C12 N1 130.00(16) . . ?
C11 C12 C7 121.23(16) . . ?
C14 C13 N1 120.74(16) . . ?
C14 C13 C18 119.75(16) . . ?
C18 C13 N1 119.50(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.78(17) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.16(16) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 S1 116.91(13) . . ?
C15 C16 C17 120.32(16) . . ?
C17 C16 S1 122.55(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.74(17) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.24(16) . . ?
C17 C18 H18 119.9 . . ?
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 O1 1.580(3) 2_655 ?
S1 O1 1.580(3) . ?
S1 C16 1.7872(18) 2_655 ?
S1 C16 1.7872(18) . ?
N1 C1 1.406(2) . ?
N1 C12 1.403(2) . ?
N1 C13 1.419(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C6 C7 1.440(3) . ?
C7 C8 1.396(2) . ?
C7 C12 1.409(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C13 C14 1.393(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 C17 1.389(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?
