#------------------------------------------------------------------------------
#$Date: 2021-08-04 14:09:36 +0300 (Wed, 04 Aug 2021) $
#$Revision: 267936 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564320.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_1564320
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 O2 S'
_chemical_formula_sum            'C36 H24 N2 O2 S'
_chemical_formula_weight         548.63
_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     dual
_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                 128.655(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.655(5)
_cell_length_b                   5.5039(11)
_cell_length_c                   20.506(4)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.506
_cell_measurement_theta_min      2.856
_cell_volume                     2525.6(9)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0551
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9461
_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         26.534
_diffrn_reflns_theta_min         1.820
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1915 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8550. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0454
_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)+(0.0413P)²+1.3158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1834
_reflns_number_total             2616
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04715e2.cif
_cod_data_source_block           mw372_0m_a
_cod_original_cell_volume        2525.6(8)
_cod_database_code               1564320
_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   0.992
_shelx_estimated_absorpt_t_min   0.950
_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 -0.18239(14) 0.250000 0.0158(2) Uani 1 2 d S T P . .
O1 O 0.46025(6) -0.3146(3) 0.25685(8) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.64881(7) 0.4374(3) 0.55212(9) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.70171(9) 0.5501(4) 0.57907(11) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.74026(9) 0.4887(4) 0.56293(12) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.731854 0.356372 0.527303 0.029 Uiso 1 1 calc R . . . .
C3 C 0.79123(10) 0.6252(4) 0.60006(12) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.818478 0.585399 0.589965 0.031 Uiso 1 1 calc R . . . .
C4 C 0.80396(10) 0.8203(4) 0.65206(12) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.839171 0.913353 0.675992 0.030 Uiso 1 1 calc R . . . .
C5 C 0.76599(9) 0.8789(4) 0.66894(11) 0.0228(5) Uani 1 1 d . . . . .
H5 H 0.774615 1.011944 0.704427 0.027 Uiso 1 1 calc R . . . .
C6 C 0.71486(9) 0.7413(4) 0.63350(11) 0.0182(5) Uani 1 1 d . . . . .
C7 C 0.66844(9) 0.7422(4) 0.64134(11) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.65765(9) 0.8912(4) 0.68567(11) 0.0219(5) Uani 1 1 d . . . . .
H8 H 0.684358 1.018996 0.719907 0.026 Uiso 1 1 calc R . . . .
C9 C 0.60743(10) 0.8484(4) 0.67857(11) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.599248 0.948159 0.708150 0.028 Uiso 1 1 calc R . . . .
C10 C 0.56854(9) 0.6615(4) 0.62882(11) 0.0229(5) Uani 1 1 d . . . . .
H10 H 0.534268 0.635422 0.625332 0.027 Uiso 1 1 calc R . . . .
C11 C 0.57820(9) 0.5118(4) 0.58412(11) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.551247 0.384368 0.550029 0.024 Uiso 1 1 calc R . . . .
C12 C 0.62859(9) 0.5551(4) 0.59103(11) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.61336(8) 0.2880(4) 0.48051(11) 0.0154(5) Uani 1 1 d . . . . .
C14 C 0.58205(9) 0.0931(4) 0.47825(11) 0.0164(5) Uani 1 1 d . . . . .
H14 H 0.585388 0.053991 0.526131 0.020 Uiso 1 1 calc R . . . .
C15 C 0.54591(9) -0.0451(4) 0.40670(11) 0.0164(5) Uani 1 1 d . . . . .
H15 H 0.523591 -0.176762 0.404670 0.020 Uiso 1 1 calc R . . . .
C16 C 0.54250(9) 0.0099(4) 0.33782(11) 0.0151(5) Uani 1 1 d . . . . .
C17 C 0.57374(9) 0.2029(4) 0.33962(11) 0.0163(5) Uani 1 1 d . . . . .
H17 H 0.571297 0.238397 0.292223 0.020 Uiso 1 1 calc R . . . .
C18 C 0.60859(9) 0.3445(4) 0.41022(11) 0.0177(5) Uani 1 1 d . . . . .
H18 H 0.629361 0.480596 0.411092 0.021 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 118.84(12) 2_655 . ?
O1 S1 C16 106.83(8) . . ?
O1 S1 C16 108.75(8) 2_655 . ?
O1 S1 C16 108.75(8) . 2_655 ?
O1 S1 C16 106.83(8) 2_655 2_655 ?
C16 S1 C16 106.19(13) 2_655 . ?
C1 N1 C12 107.61(16) . . ?
C1 N1 C13 124.64(16) . . ?
C12 N1 C13 125.07(17) . . ?
N1 C1 C6 109.53(18) . . ?
C2 C1 N1 129.21(19) . . ?
C2 C1 C6 121.2(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.53(18) . . ?
C5 C6 C1 119.86(19) . . ?
C5 C6 C7 133.59(19) . . ?
C8 C7 C6 132.3(2) . . ?
C8 C7 C12 120.14(19) . . ?
C12 C7 C6 107.53(17) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 H11 121.3 . . ?
C7 C12 N1 108.79(17) . . ?
C11 C12 N1 129.71(19) . . ?
C11 C12 C7 121.48(18) . . ?
C14 C13 N1 121.13(17) . . ?
C14 C13 C18 119.75(17) . . ?
C18 C13 N1 119.08(19) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.30(18) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 S1 118.27(16) . . ?
C17 C16 S1 120.94(14) . . ?
C17 C16 C15 120.72(18) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.87(18) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 119.9(2) . . ?
C17 C18 H18 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
S1 O1 1.4305(14) 2_655 ?
S1 O1 1.4306(14) . ?
S1 C16 1.7623(19) 2_655 ?
S1 C16 1.7624(19) . ?
N1 C1 1.393(3) . ?
N1 C12 1.403(2) . ?
N1 C13 1.415(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.436(3) . ?
C7 C8 1.395(3) . ?
C7 C12 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C13 C14 1.380(3) . ?
C13 C18 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?
