#------------------------------------------------------------------------------
#$Date: 2022-01-13 00:59:32 +0200 (Thu, 13 Jan 2022) $
#$Revision: 272009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129554.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_7129554
loop_
_publ_author_name
'Zhang, Huaxing'
'Guo, Qiang'
'Cheng, Hu'
'Ran, Chunhao'
'Wu, Di'
'Lan, Jingbo'
_publ_section_title
;
 An umpolung strategy for rapid access to thermally activated delayed
 fluorescence (TADF) materials based on phenazine
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06705B
_journal_year                    2022
_chemical_formula_moiety         'C24 H15 N3 S'
_chemical_formula_sum            'C24 H15 N3 S'
_chemical_formula_weight         377.45
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-11-01 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.281(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2292(3)
_cell_length_b                   16.3951(5)
_cell_length_c                   11.6492(3)
_cell_measurement_reflns_used    3413
_cell_measurement_temperature    295.7(2)
_cell_measurement_theta_max      71.3450
_cell_measurement_theta_min      4.9010
_cell_volume                     1794.60(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.7(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    2.37    --  -36.29 -38.00  90.00   88
  2  ω   -105.00 -17.00   1.00    2.37    --  -36.29 -38.00 -30.00   88
  3  ω      1.00  75.00   1.00    2.37    --   36.29 -99.00 -60.00   74
  4  ω      1.00  75.00   1.00    2.37    --   36.29 -99.00-180.00   74
  5  ω     17.00 105.00   1.00    2.37    --   36.29  38.00 -60.00   88
  6  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00   0.00   72
  7  ω     36.00 128.00   1.00    9.50    --  106.21 -30.00  30.00   92
  8  ω     89.00 175.00   1.00    9.50    --  106.21  45.00 120.00   86
  9  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00 120.00   72
 10  ω     89.00 175.00   1.00    9.50    --  106.21  45.00-150.00   86
 11  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00-120.00   72
 12  ω     79.00 174.00   1.00    9.50    --  106.21  77.00 -30.00   95
 13  ω     38.00  88.00   1.00    9.50    --  106.21 -45.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1604923000
_diffrn_orient_matrix_UB_12      0.0183038000
_diffrn_orient_matrix_UB_13      0.0631776000
_diffrn_orient_matrix_UB_21      -0.0315162000
_diffrn_orient_matrix_UB_22      0.0920971000
_diffrn_orient_matrix_UB_23      -0.0176709000
_diffrn_orient_matrix_UB_31      -0.0106826000
_diffrn_orient_matrix_UB_32      0.0036389000
_diffrn_orient_matrix_UB_33      0.1281880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8706
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.561
_diffrn_reflns_theta_min         4.706
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0628
_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)+(0.1243P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2957
_reflns_number_total             3377
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06705b2.cif
_cod_data_source_block           yjs-zhx-41-3
_cod_database_code               7129554
_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.
;
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.775
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
S001 S 0.30172(6) 0.58798(4) -0.08245(5) 0.0579(2) Uani 1 1 d . . . . .
N002 N 0.43826(16) 0.68182(11) 0.15059(15) 0.0438(4) Uani 1 1 d . . . . .
N003 N 0.79894(17) 0.54838(11) 0.49617(15) 0.0449(4) Uani 1 1 d . . . . .
N004 N 0.62995(18) 0.56410(10) 0.63844(15) 0.0418(4) Uani 1 1 d . . . . .
C005 C 0.67011(19) 0.58313(11) 0.44855(17) 0.0385(4) Uani 1 1 d . . . . .
C006 C 0.29505(19) 0.70708(13) 0.08000(17) 0.0421(4) Uani 1 1 d . . . . .
C007 C 0.58544(19) 0.59121(11) 0.52081(17) 0.0367(4) Uani 1 1 d . . . . .
C008 C 0.48787(19) 0.65100(11) 0.27213(16) 0.0378(4) Uani 1 1 d . . . . .
C009 C 0.7583(2) 0.52746(11) 0.68541(17) 0.0407(4) Uani 1 1 d . . . . .
C00A C 0.61792(19) 0.61270(13) 0.32437(17) 0.0417(4) Uani 1 1 d . . . . .
H00A H 0.6724 0.6062 0.2773 0.050 Uiso 1 1 calc R . . . .
C00B C 0.8434(2) 0.52011(12) 0.61417(17) 0.0416(4) Uani 1 1 d . . . . .
C00C C 0.52368(19) 0.67553(12) 0.07893(17) 0.0411(4) Uani 1 1 d . . . . .
C00D C 0.44967(19) 0.62878(12) 0.46313(17) 0.0402(4) Uani 1 1 d . . . . .
H00D H 0.3920 0.6336 0.5076 0.048 Uiso 1 1 calc R . . . .
C00E C 0.40266(18) 0.65767(12) 0.34457(18) 0.0400(4) Uani 1 1 d . . . . .
H00E H 0.3136 0.6823 0.3095 0.048 Uiso 1 1 calc R . . . .
C00F C 0.2194(2) 0.66841(14) -0.03361(18) 0.0476(5) Uani 1 1 d . . . . .
C00G C 0.8093(2) 0.49297(14) 0.80775(18) 0.0497(5) Uani 1 1 d . . . . .
H00G H 0.7554 0.4974 0.8557 0.060 Uiso 1 1 calc R . . . .
C00H C 0.9369(3) 0.45365(14) 0.85438(19) 0.0543(5) Uani 1 1 d . . . . .
H00H H 0.9681 0.4300 0.9333 0.065 Uiso 1 1 calc R . . . .
C00I C 0.2351(2) 0.77280(14) 0.1164(2) 0.0505(5) Uani 1 1 d . . . . .
H00I H 0.2863 0.8000 0.1908 0.061 Uiso 1 1 calc R . . . .
C00J C 0.5542(3) 0.62571(15) -0.1036(2) 0.0558(5) Uani 1 1 d . . . . .
H00J H 0.5201 0.5963 -0.1780 0.067 Uiso 1 1 calc R . . . .
C00K C 0.6528(2) 0.71629(13) 0.11526(19) 0.0456(5) Uani 1 1 d . . . . .
H00K H 0.6851 0.7480 0.1874 0.055 Uiso 1 1 calc R . . . .
C00L C 0.9779(2) 0.48065(15) 0.6675(2) 0.0529(5) Uani 1 1 d . . . . .
H00L H 1.0354 0.4769 0.6226 0.063 Uiso 1 1 calc R . . . .
C00M C 0.4738(2) 0.63180(13) -0.03173(18) 0.0459(5) Uani 1 1 d . . . . .
C00N C 0.7334(2) 0.70976(15) 0.0440(2) 0.0538(5) Uani 1 1 d . . . . .
H00N H 0.8205 0.7365 0.0689 0.065 Uiso 1 1 calc R . . . .
C00O C 0.6845(3) 0.66352(16) -0.0640(2) 0.0577(6) Uani 1 1 d . . . . .
H00O H 0.7402 0.6580 -0.1102 0.069 Uiso 1 1 calc R . . . .
C00P C 1.0224(2) 0.44830(15) 0.7846(2) 0.0559(5) Uani 1 1 d . . . . .
H00P H 1.1103 0.4224 0.8191 0.067 Uiso 1 1 calc R . . . .
C00Q C 0.0227(2) 0.7586(2) -0.0697(3) 0.0711(8) Uani 1 1 d . . . . .
H00Q H -0.0695 0.7753 -0.1189 0.085 Uiso 1 1 calc R . . . .
C00R C 0.0977(2) 0.79784(17) 0.0411(3) 0.0641(7) Uani 1 1 d . . . . .
H00R H 0.0566 0.8414 0.0659 0.077 Uiso 1 1 calc R . . . .
C00S C 0.0830(2) 0.69410(19) -0.1089(2) 0.0637(7) Uani 1 1 d . . . . .
H00S H 0.0325 0.6684 -0.1848 0.076 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C00M S001 C00F 97.27(10) . . ?
C006 N002 C00C 114.12(15) . . ?
C008 N002 C006 124.58(16) . . ?
C008 N002 C00C 120.29(15) . . ?
C005 N003 C00B 116.71(16) . . ?
C007 N004 C009 116.52(16) . . ?
N003 C005 C007 121.38(17) . . ?
N003 C005 C00A 118.78(17) . . ?
C00A C005 C007 119.83(16) . . ?
C00F C006 N002 118.22(19) . . ?
C00I C006 N002 121.73(19) . . ?
C00I C006 C00F 119.82(18) . . ?
N004 C007 C005 122.08(17) . . ?
N004 C007 C00D 120.09(16) . . ?
C00D C007 C005 117.83(16) . . ?
N002 C008 C00E 120.41(16) . . ?
C00A C008 N002 120.92(16) . . ?
C00A C008 C00E 118.66(16) . . ?
N004 C009 C00B 121.50(17) . . ?
N004 C009 C00G 119.68(18) . . ?
C00B C009 C00G 118.79(18) . . ?
C005 C00A H00A 119.4 . . ?
C008 C00A C005 121.10(17) . . ?
C008 C00A H00A 119.4 . . ?
N003 C00B C009 121.79(17) . . ?
N003 C00B C00L 118.71(18) . . ?
C00L C00B C009 119.49(17) . . ?
C00K C00C N002 120.93(18) . . ?
C00M C00C N002 119.69(18) . . ?
C00M C00C C00K 119.29(18) . . ?
C007 C00D H00D 119.3 . . ?
C00E C00D C007 121.31(16) . . ?
C00E C00D H00D 119.3 . . ?
C008 C00E H00E 119.4 . . ?
C00D C00E C008 121.22(16) . . ?
C00D C00E H00E 119.4 . . ?
C006 C00F S001 119.12(15) . . ?
C00S C00F S001 120.60(19) . . ?
C00S C00F C006 120.3(2) . . ?
C009 C00G H00G 120.0 . . ?
C00H C00G C009 120.1(2) . . ?
C00H C00G H00G 120.0 . . ?
C00G C00H H00H 119.5 . . ?
C00G C00H C00P 120.91(18) . . ?
C00P C00H H00H 119.5 . . ?
C006 C00I H00I 120.2 . . ?
C006 C00I C00R 119.6(2) . . ?
C00R C00I H00I 120.2 . . ?
C00M C00J H00J 120.3 . . ?
C00O C00J H00J 120.3 . . ?
C00O C00J C00M 119.4(2) . . ?
C00C C00K H00K 120.0 . . ?
C00N C00K C00C 120.0(2) . . ?
C00N C00K H00K 120.0 . . ?
C00B C00L H00L 120.1 . . ?
C00P C00L C00B 119.8(2) . . ?
C00P C00L H00L 120.1 . . ?
C00C C00M S001 118.18(15) . . ?
C00C C00M C00J 120.7(2) . . ?
C00J C00M S001 121.07(17) . . ?
C00K C00N H00N 120.0 . . ?
C00O C00N C00K 120.0(2) . . ?
C00O C00N H00N 120.0 . . ?
C00J C00O C00N 120.49(19) . . ?
C00J C00O H00O 119.8 . . ?
C00N C00O H00O 119.8 . . ?
C00H C00P H00P 119.5 . . ?
C00L C00P C00H 120.9(2) . . ?
C00L C00P H00P 119.5 . . ?
C00R C00Q H00Q 119.7 . . ?
C00R C00Q C00S 120.6(2) . . ?
C00S C00Q H00Q 119.7 . . ?
C00I C00R H00R 119.9 . . ?
C00Q C00R C00I 120.3(2) . . ?
C00Q C00R H00R 119.9 . . ?
C00F C00S C00Q 119.3(2) . . ?
C00F C00S H00S 120.3 . . ?
C00Q C00S H00S 120.3 . . ?
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
S001 C00F 1.775(2) . ?
S001 C00M 1.773(2) . ?
N002 C006 1.429(2) . ?
N002 C008 1.396(2) . ?
N002 C00C 1.431(2) . ?
N003 C005 1.338(2) . ?
N003 C00B 1.348(2) . ?
N004 C007 1.338(2) . ?
N004 C009 1.348(3) . ?
C005 C007 1.433(3) . ?
C005 C00A 1.415(3) . ?
C006 C00F 1.394(3) . ?
C006 C00I 1.387(3) . ?
C007 C00D 1.422(3) . ?
C008 C00A 1.376(3) . ?
C008 C00E 1.437(3) . ?
C009 C00B 1.426(3) . ?
C009 C00G 1.427(3) . ?
C00A H00A 0.9300 . ?
C00B C00L 1.422(3) . ?
C00C C00K 1.388(3) . ?
C00C C00M 1.384(3) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.356(3) . ?
C00E H00E 0.9300 . ?
C00F C00S 1.388(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.361(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.413(3) . ?
C00I H00I 0.9300 . ?
C00I C00R 1.392(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.390(3) . ?
C00J C00O 1.374(4) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.387(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.364(3) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.382(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.373(4) . ?
C00Q C00S 1.389(4) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
