#------------------------------------------------------------------------------
#$Date: 2022-01-13 00:59:32 +0200 (Thu, 13 Jan 2022) $
#$Revision: 272009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129559.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_7129559
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         'C12 H7 N3 O2'
_chemical_formula_sum            'C12 H7 N3 O2'
_chemical_formula_weight         225.21
_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             2020-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-10-30 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.235(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8370(4)
_cell_length_b                   22.4145(11)
_cell_length_c                   7.1605(4)
_cell_measurement_reflns_used    1588
_cell_measurement_temperature    296.4(8)
_cell_measurement_theta_max      70.4490
_cell_measurement_theta_min      5.7320
_cell_volume                     1000.62(11)
_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      296.4(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  33.00   1.00    4.49    --  -34.98  57.00  30.00   86
  2  ω    -34.00  64.00   1.00    4.49    --   34.98 -77.00-150.00   98
  3  ω     16.00 103.00   1.00    4.49    --   34.98  57.00  60.00   87
  4  ω    -34.00  64.00   1.00    4.49    --   34.98 -77.00 -60.00   98
  5  ω      1.00  75.00   1.00    4.49    --   34.98 -99.00  90.00   74
  6  ω    100.00 178.00   1.00   17.97    --  106.90 111.00-120.00   78
  7  ω     78.00 176.00   1.00   17.97    --  106.90  77.00-120.00   98
  8  ω    100.00 178.00   1.00   17.97    --  106.90 111.00 -30.00   78
  9  ω     61.00 178.00   1.00   17.97    --  106.90  15.00 -60.00  117
 10  ω    100.00 178.00   1.00   17.97    --  106.90 111.00 120.00   78
 11  ω     36.00 113.00   1.00   17.97    --  106.90-111.00-180.00   77
 12  ω     37.00 110.00   1.00   17.97    --  106.90 -94.00  30.00   73
 13  ω    100.00 178.00   1.00   17.97    --  106.90 111.00   0.00   78
 14  ω   -103.00 -16.00   1.00    4.49    --  -34.98 -57.00-120.00   87
 15  ω     16.00 103.00   1.00    4.49    --   34.98  57.00 150.00   87
;
_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      -0.0233045000
_diffrn_orient_matrix_UB_12      -0.0668973000
_diffrn_orient_matrix_UB_13      -0.0541163000
_diffrn_orient_matrix_UB_21      0.1568401000
_diffrn_orient_matrix_UB_22      0.0070730000
_diffrn_orient_matrix_UB_23      -0.1034164000
_diffrn_orient_matrix_UB_31      0.1895876000
_diffrn_orient_matrix_UB_32      -0.0140289000
_diffrn_orient_matrix_UB_33      0.2049786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.269
_diffrn_reflns_theta_min         3.944
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73475
_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    1.495
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0702
_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)+(0.1413P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2204
_refine_ls_wR_factor_ref         0.2332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1510
_reflns_number_total             1917
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06705b2.cif
_cod_data_source_block           zhx-no2
_cod_original_cell_volume        1000.63(10)
_cod_database_code               7129559
_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 99.84
_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:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-09-08
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.520
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
N001 N 0.9247(2) 0.47964(8) 0.7127(2) 0.0396(5) Uani 1 1 d . . . . .
N002 N 0.5743(2) 0.52263(8) 0.7907(2) 0.0408(5) Uani 1 1 d . . . . .
O003 O 0.4510(4) 0.25353(9) 0.5568(4) 0.0865(7) Uani 1 1 d . . . . .
C004 C 0.5869(3) 0.46547(9) 0.7429(3) 0.0386(5) Uani 1 1 d . . . . .
C005 C 0.9124(3) 0.53681(9) 0.7609(3) 0.0377(5) Uani 1 1 d . . . . .
C006 C 0.7357(3) 0.55853(9) 0.8008(3) 0.0387(5) Uani 1 1 d . . . . .
C007 C 0.7626(3) 0.44414(9) 0.7019(3) 0.0380(5) Uani 1 1 d . . . . .
O008 O 0.7482(4) 0.26895(9) 0.5288(4) 0.0909(8) Uani 1 1 d . . . . .
N009 N 0.6010(4) 0.28545(9) 0.5702(3) 0.0617(6) Uani 1 1 d . . . . .
C00A C 0.6009(3) 0.34757(9) 0.6364(3) 0.0464(6) Uani 1 1 d . . . . .
C00B C 0.7651(3) 0.38330(10) 0.6466(3) 0.0435(5) Uani 1 1 d . . . . .
H00B H 0.8767 0.3684 0.6181 0.052 Uiso 1 1 calc R . . . .
C00C C 0.7320(3) 0.61970(10) 0.8514(3) 0.0462(6) Uani 1 1 d . . . . .
H00C H 0.6192 0.6344 0.8785 0.055 Uiso 1 1 calc R . . . .
C00D C 0.4291(3) 0.36720(10) 0.6798(3) 0.0498(6) Uani 1 1 d . . . . .
H00D H 0.3220 0.3407 0.6739 0.060 Uiso 1 1 calc R . . . .
C00E C 1.0782(3) 0.57705(10) 0.7726(3) 0.0451(5) Uani 1 1 d . . . . .
H00E H 1.1943 0.5635 0.7484 0.054 Uiso 1 1 calc R . . . .
C00F C 0.4207(3) 0.42496(10) 0.7303(3) 0.0462(6) Uani 1 1 d . . . . .
H00F H 0.3061 0.4384 0.7571 0.055 Uiso 1 1 calc R . . . .
C00G C 1.0665(3) 0.63510(10) 0.8190(4) 0.0508(6) Uani 1 1 d . . . . .
H00G H 1.1739 0.6613 0.8242 0.061 Uiso 1 1 calc R . . . .
C00H C 0.8922(4) 0.65667(10) 0.8602(3) 0.0515(6) Uani 1 1 d . . . . .
H00H H 0.8884 0.6966 0.8935 0.062 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'
O O 0.0492 0.0322 '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
C005 N001 C007 116.45(17) . . ?
C004 N002 C006 116.74(17) . . ?
N002 C004 C007 121.32(19) . . ?
N002 C004 C00F 119.47(18) . . ?
C00F C004 C007 119.2(2) . . ?
N001 C005 C006 121.52(19) . . ?
N001 C005 C00E 119.28(18) . . ?
C00E C005 C006 119.20(19) . . ?
N002 C006 C005 121.71(19) . . ?
N002 C006 C00C 119.46(18) . . ?
C00C C006 C005 118.83(19) . . ?
N001 C007 C004 122.26(19) . . ?
N001 C007 C00B 118.78(18) . . ?
C00B C007 C004 118.96(19) . . ?
O003 N009 C00A 117.9(2) . . ?
O008 N009 O003 123.7(2) . . ?
O008 N009 C00A 118.4(2) . . ?
C00B C00A N009 117.8(2) . . ?
C00B C00A C00D 123.5(2) . . ?
C00D C00A N009 118.6(2) . . ?
C007 C00B H00B 120.7 . . ?
C00A C00B C007 118.52(19) . . ?
C00A C00B H00B 120.7 . . ?
C006 C00C H00C 119.9 . . ?
C00H C00C C006 120.26(19) . . ?
C00H C00C H00C 119.9 . . ?
C00A C00D H00D 120.3 . . ?
C00F C00D C00A 119.4(2) . . ?
C00F C00D H00D 120.3 . . ?
C005 C00E H00E 120.1 . . ?
C00G C00E C005 119.81(19) . . ?
C00G C00E H00E 120.1 . . ?
C004 C00F H00F 119.8 . . ?
C00D C00F C004 120.4(2) . . ?
C00D C00F H00F 119.8 . . ?
C00E C00G H00G 119.5 . . ?
C00E C00G C00H 121.1(2) . . ?
C00H C00G H00G 119.5 . . ?
C00C C00H C00G 120.8(2) . . ?
C00C C00H H00H 119.6 . . ?
C00G C00H H00H 119.6 . . ?
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
N001 C005 1.338(3) . ?
N001 C007 1.340(3) . ?
N002 C004 1.338(3) . ?
N002 C006 1.343(3) . ?
O003 N009 1.221(3) . ?
C004 C007 1.431(3) . ?
C004 C00F 1.428(3) . ?
C005 C006 1.436(3) . ?
C005 C00E 1.424(3) . ?
C006 C00C 1.421(3) . ?
C007 C00B 1.422(3) . ?
O008 N009 1.217(3) . ?
N009 C00A 1.471(3) . ?
C00A C00B 1.356(3) . ?
C00A C00D 1.403(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.354(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.352(3) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.353(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.424(3) . ?
C00H H00H 0.9300 . ?
