#------------------------------------------------------------------------------
#$Date: 2022-01-13 00:59:32 +0200 (Thu, 13 Jan 2022) $
#$Revision: 272009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129553.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_7129553
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 F2 N3'
_chemical_formula_sum            'C24 H15 F2 N3'
_chemical_formula_weight         383.39
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.16800(11)
_cell_length_b                   22.8606(4)
_cell_length_c                   23.0265(5)
_cell_measurement_reflns_used    3512
_cell_measurement_temperature    296.75(10)
_cell_measurement_theta_max      71.5760
_cell_measurement_theta_min      3.8350
_cell_volume                     3773.23(12)
_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      296.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.90    --  -36.17 -57.00 -30.00   84
  2  ω     23.00  90.00   1.00    1.90    --   36.17-125.00 120.00   67
  3  ω      7.00 108.00   1.00    1.90    --   36.17  19.00 120.00  101
  4  ω    100.00 176.00   1.00    7.60    --  106.21 111.00 -30.00   76
  5  ω    100.00 176.00   1.00    7.60    --  106.21 111.00 120.00   76
  6  ω     36.00 113.00   1.00    7.60    --  106.21-111.00 120.00   77
  7  ω     38.00 124.00   1.00    7.60    --  106.21 -45.00-150.00   86
  8  ω     37.00 109.00   1.00    7.60    --  106.21 -94.00-180.00   72
  9  ω   -105.00 -79.00   1.00    1.90    --  -36.17 -38.00-150.00   26
;
_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      0.0366230000
_diffrn_orient_matrix_UB_12      -0.0664007000
_diffrn_orient_matrix_UB_13      -0.0006136000
_diffrn_orient_matrix_UB_21      -0.0667831000
_diffrn_orient_matrix_UB_22      -0.0041836000
_diffrn_orient_matrix_UB_23      0.0634426000
_diffrn_orient_matrix_UB_31      -0.2010395000
_diffrn_orient_matrix_UB_32      -0.0106939000
_diffrn_orient_matrix_UB_33      -0.0211810000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.446
_diffrn_reflns_theta_min         3.839
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56056
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0662
_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)+(0.1163P)²+0.4030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2970
_reflns_number_total             3607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06705b2.cif
_cod_data_source_block           zhx-4148
_cod_original_cell_volume        3773.23(13)
_cod_database_code               7129553
_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 99.87
_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:
 C009(H009), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-03
_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 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.723
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
F001 F 0.4536(2) 0.33820(6) 0.07638(7) 0.0721(4) Uani 1 1 d . . . . .
F002 F 0.3882(3) 0.43667(7) 0.01866(6) 0.0805(5) Uani 1 1 d . . . . .
N003 N 0.2951(2) 0.53999(6) 0.19418(7) 0.0422(4) Uani 1 1 d . . . . .
N004 N 0.2636(2) 0.64311(7) 0.37581(7) 0.0451(4) Uani 1 1 d . . . . .
N005 N 0.3691(2) 0.43468(6) 0.25584(7) 0.0416(4) Uani 1 1 d . . . . .
C006 C 0.1670(3) 0.69188(7) 0.35150(8) 0.0415(4) Uani 1 1 d . . . . .
C007 C 0.2981(2) 0.53834(7) 0.25248(8) 0.0379(4) Uani 1 1 d . . . . .
C008 C 0.3361(2) 0.48494(7) 0.28351(8) 0.0382(4) Uani 1 1 d . . . . .
C009 C 0.2720(2) 0.59091(7) 0.28398(8) 0.0407(4) Uani 1 1 d . . . . .
H009 H 0.2467 0.6254 0.2641 0.049 Uiso 1 1 calc R . . . .
C00A C 0.2834(2) 0.59149(7) 0.34318(8) 0.0401(4) Uani 1 1 d . . . . .
C00B C 0.3684(2) 0.43648(8) 0.19758(8) 0.0400(4) Uani 1 1 d . . . . .
C00C C 0.3323(2) 0.48945(8) 0.16644(8) 0.0412(4) Uani 1 1 d . . . . .
C00D C 0.3904(3) 0.65322(8) 0.42253(8) 0.0442(4) Uani 1 1 d . . . . .
C00E C 0.2514(3) 0.74633(8) 0.34794(9) 0.0491(5) Uani 1 1 d . . . . .
H00E H 0.3730 0.7514 0.3611 0.059 Uiso 1 1 calc R . . . .
C00F C -0.0141(3) 0.68501(9) 0.33204(9) 0.0511(5) Uani 1 1 d . . . . .
H00F H -0.0723 0.6488 0.3348 0.061 Uiso 1 1 calc R . . . .
C00G C 0.3401(3) 0.48684(8) 0.34511(8) 0.0440(4) Uani 1 1 d . . . . .
H00G H 0.3602 0.4526 0.3659 0.053 Uiso 1 1 calc R . . . .
C00H C 0.4089(3) 0.38457(8) 0.16594(9) 0.0477(5) Uani 1 1 d . . . . .
H00H H 0.4323 0.3497 0.1854 0.057 Uiso 1 1 calc R . . . .
C00I C 0.3150(3) 0.53785(8) 0.37398(8) 0.0437(4) Uani 1 1 d . . . . .
H00I H 0.3183 0.5381 0.4144 0.052 Uiso 1 1 calc R . . . .
C00J C 0.1543(3) 0.79322(9) 0.32470(10) 0.0549(5) Uani 1 1 d . . . . .
H00J H 0.2111 0.8297 0.3226 0.066 Uiso 1 1 calc R . . . .
C00K C 0.3368(3) 0.48894(9) 0.10468(9) 0.0517(5) Uani 1 1 d . . . . .
H00K H 0.3117 0.5228 0.0838 0.062 Uiso 1 1 calc R . . . .
C00L C 0.5754(3) 0.63600(10) 0.41859(10) 0.0566(5) Uani 1 1 d . . . . .
H00L H 0.6186 0.6176 0.3852 0.068 Uiso 1 1 calc R . . . .
C00M C 0.3279(3) 0.68111(9) 0.47212(9) 0.0546(5) Uani 1 1 d . . . . .
H00M H 0.2041 0.6930 0.4749 0.066 Uiso 1 1 calc R . . . .
C00N C 0.4131(3) 0.38638(9) 0.10778(9) 0.0516(5) Uani 1 1 d . . . . .
C00O C -0.0242(3) 0.78635(10) 0.30489(10) 0.0589(5) Uani 1 1 d . . . . .
H00O H -0.0883 0.8180 0.2892 0.071 Uiso 1 1 calc R . . . .
C00P C 0.3781(3) 0.43861(10) 0.07678(9) 0.0547(5) Uani 1 1 d . . . . .
C00Q C -0.1090(3) 0.73221(10) 0.30833(11) 0.0604(6) Uani 1 1 d . . . . .
H00Q H -0.2301 0.7274 0.2947 0.073 Uiso 1 1 calc R . . . .
C00R C 0.4487(4) 0.69130(12) 0.51742(11) 0.0696(7) Uani 1 1 d . . . . .
H00R H 0.4067 0.7104 0.5506 0.084 Uiso 1 1 calc R . . . .
C00S C 0.6952(3) 0.64620(12) 0.46442(13) 0.0725(7) Uani 1 1 d . . . . .
H00S H 0.8193 0.6346 0.4618 0.087 Uiso 1 1 calc R . . . .
C00T C 0.6321(4) 0.67330(12) 0.51380(12) 0.0757(7) Uani 1 1 d . . . . .
H00T H 0.7128 0.6795 0.5448 0.091 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'
F F 0.0727 0.0534 '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'
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
C007 N003 C00C 116.54(15) . . ?
C006 N004 C00D 118.57(15) . . ?
C00A N004 C006 119.68(15) . . ?
C00A N004 C00D 118.30(15) . . ?
C008 N005 C00B 116.73(15) . . ?
C00E C006 N004 120.88(17) . . ?
C00F C006 N004 119.62(16) . . ?
C00F C006 C00E 119.50(18) . . ?
N003 C007 C008 121.51(15) . . ?
N003 C007 C009 119.08(15) . . ?
C009 C007 C008 119.35(16) . . ?
N005 C008 C007 121.75(16) . . ?
N005 C008 C00G 119.97(16) . . ?
C00G C008 C007 118.27(15) . . ?
C007 C009 H009 119.6 . . ?
C00A C009 C007 120.76(16) . . ?
C00A C009 H009 119.6 . . ?
N004 C00A C00I 117.98(16) . . ?
C009 C00A N004 122.37(16) . . ?
C009 C00A C00I 119.65(16) . . ?
N005 C00B C00C 121.85(15) . . ?
N005 C00B C00H 119.04(16) . . ?
C00H C00B C00C 119.09(18) . . ?
N003 C00C C00B 121.61(17) . . ?
N003 C00C C00K 119.06(17) . . ?
C00K C00C C00B 119.33(16) . . ?
C00L C00D N004 120.93(18) . . ?
C00M C00D N004 119.38(18) . . ?
C00M C00D C00L 119.69(19) . . ?
C006 C00E H00E 120.1 . . ?
C00J C00E C006 119.89(19) . . ?
C00J C00E H00E 120.1 . . ?
C006 C00F H00F 120.0 . . ?
C006 C00F C00Q 119.99(19) . . ?
C00Q C00F H00F 120.0 . . ?
C008 C00G H00G 119.5 . . ?
C00I C00G C008 120.94(16) . . ?
C00I C00G H00G 119.5 . . ?
C00B C00H H00H 120.3 . . ?
C00N C00H C00B 119.38(18) . . ?
C00N C00H H00H 120.3 . . ?
C00A C00I H00I 119.5 . . ?
C00G C00I C00A 120.95(17) . . ?
C00G C00I H00I 119.5 . . ?
C00E C00J H00J 119.7 . . ?
C00O C00J C00E 120.66(19) . . ?
C00O C00J H00J 119.7 . . ?
C00C C00K H00K 120.4 . . ?
C00P C00K C00C 119.18(19) . . ?
C00P C00K H00K 120.4 . . ?
C00D C00L H00L 120.1 . . ?
C00S C00L C00D 119.8(2) . . ?
C00S C00L H00L 120.1 . . ?
C00D C00M H00M 120.0 . . ?
C00R C00M C00D 120.0(2) . . ?
C00R C00M H00M 120.0 . . ?
F001 C00N C00P 117.21(19) . . ?
C00H C00N F001 121.00(19) . . ?
C00H C00N C00P 121.79(18) . . ?
C00J C00O H00O 120.2 . . ?
C00J C00O C00Q 119.7(2) . . ?
C00Q C00O H00O 120.2 . . ?
F002 C00P C00K 121.0(2) . . ?
F002 C00P C00N 117.80(18) . . ?
C00K C00P C00N 121.2(2) . . ?
C00F C00Q H00Q 119.9 . . ?
C00O C00Q C00F 120.3(2) . . ?
C00O C00Q H00Q 119.9 . . ?
C00M C00R H00R 119.9 . . ?
C00M C00R C00T 120.2(2) . . ?
C00T C00R H00R 119.9 . . ?
C00L C00S H00S 119.8 . . ?
C00T C00S C00L 120.3(2) . . ?
C00T C00S H00S 119.8 . . ?
C00R C00T H00T 120.0 . . ?
C00S C00T C00R 119.9(2) . . ?
C00S C00T H00T 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
F001 C00N 1.349(2) . ?
F002 C00P 1.341(2) . ?
N003 C007 1.343(2) . ?
N003 C00C 1.347(2) . ?
N004 C006 1.427(2) . ?
N004 C00A 1.406(2) . ?
N004 C00D 1.427(2) . ?
N005 C008 1.335(2) . ?
N005 C00B 1.342(2) . ?
C006 C00E 1.386(3) . ?
C006 C00F 1.382(3) . ?
C007 C008 1.440(2) . ?
C007 C009 1.416(2) . ?
C008 C00G 1.419(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.366(3) . ?
C00A C00I 1.435(3) . ?
C00B C00C 1.431(3) . ?
C00B C00H 1.422(2) . ?
C00C C00K 1.423(3) . ?
C00D C00L 1.386(3) . ?
C00D C00M 1.383(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.386(3) . ?
C00F H00F 0.9300 . ?
C00F C00Q 1.387(3) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.354(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.340(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00O 1.368(3) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.350(3) . ?
C00L H00L 0.9300 . ?
C00L C00S 1.380(3) . ?
C00M H00M 0.9300 . ?
C00M C00R 1.376(3) . ?
C00N C00P 1.413(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.381(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00T 1.380(4) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.372(4) . ?
C00T H00T 0.9300 . ?
