Understanding the nature of quinoidal and zwitterionic states in carbazole-based diradicals.
Xue, Guodong; Hu, Xiaoguang; Chen, Hanjiao; Ge, Lingbing; Wang, Wenxiang; Xiong, Jingyuan; Miao, Fang; Zheng, Yonghao; Chemical communications (Cambridge, England) 56 (2020) 5143–5146; doi:10.1039/d0cc01948h

data_7126352
_publ_section_title
;
 Understanding the nature of quinoidal and zwitterionic states in
 carbazole-based diradicals.
;
_journal_issue                   38
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5143
_journal_page_last               5146
_journal_paper_doi               10.1039/d0cc01948h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C48 H64.61 N O2'
_chemical_formula_sum            'C48 H65 N O2'
_chemical_formula_weight         688.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-13 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7639(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1364(3)
_cell_length_b                   17.5731(4)
_cell_length_c                   22.0778(4)
_cell_measurement_reflns_used    7212
_cell_measurement_temperature    293.32(18)
_cell_measurement_theta_max      71.0650
_cell_measurement_theta_min      3.6750
_cell_volume                     4703.15(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      293.32(18)
_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 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  31.00   1.00    2.58    --  -36.17  57.00 120.00   84
  2  \w   -103.00 -19.00   1.00    2.58    --  -36.17 -57.00 150.00   84
  3  \w   -104.00  -9.00   1.00    2.58    --  -36.17 -77.00-120.00   95
  4  \w      7.00 108.00   1.00    2.58    --   36.17  19.00 -60.00  101
  5  \w     19.00 103.00   1.00    2.58    --   36.17  57.00   0.00   84
  6  \w     23.00  90.00   1.00    2.58    --   36.17-125.00-180.00   67
  7  \w     91.00 176.00   1.00   10.31    --  108.71  61.00 120.00   85
  8  \w     40.00 126.00   1.00   10.31    --  108.71 -45.00-150.00   86
  9  \w     42.00 127.00   1.00   10.31    --  108.71 -61.00 -60.00   85
 10  \w     39.00 109.00   1.00   10.31    --  108.71 -94.00   0.00   70
 11  \w     39.00 115.00   1.00   10.31    --  108.71-111.00 -90.00   76
 12  \w     39.00 109.00   1.00   10.31    --  108.71 -94.00 -60.00   70
 13  \w     39.00 178.00   1.00   10.31    --  108.71   0.00  90.00  139
 14  \w   -104.00 -20.00   1.00    2.58    --  -36.17 -77.00  60.00   84
 15  \w    -53.00  31.00   1.00    2.58    --  -36.17  57.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1254339000
_diffrn_orient_matrix_UB_12      0.0064764000
_diffrn_orient_matrix_UB_13      0.0067149000
_diffrn_orient_matrix_UB_21      -0.0160511000
_diffrn_orient_matrix_UB_22      0.0174569000
_diffrn_orient_matrix_UB_23      -0.0682326000
_diffrn_orient_matrix_UB_31      -0.0127417000
_diffrn_orient_matrix_UB_32      -0.0856547000
_diffrn_orient_matrix_UB_33      -0.0134060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.896
_diffrn_reflns_theta_min         4.009
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.972
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         9218
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0711
_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/[\s^2^(Fo^2^)+(0.1312P)^2^+0.9699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6584
_reflns_number_total             9218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01948h2.cif
_cod_data_source_block           Cb27OH
_cod_depositor_comments          'Adding full bibliography for 7126352.cif.'
_cod_original_cell_volume        4703.14(17)
_cod_database_code               7126352
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C01E, C01F, C1AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01E \\sim C01F \\sim C1AA: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C01E) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(HG)=Sof(HH)=Sof(HI)=Sof(C1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(H00Y)=Sof(H0AA)=Sof(HE)=Sof(HF)=Sof(C01F)=Sof(H1AA)=Sof(HJ)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00Y(H00Y)
5.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C01A(H01,HD), C01F(H1AA,HJ), C01G(H2AA,HK), C0AA(H0AB,H0AC),
 C1AA(H1AB,H1AC)
5.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00N(H00N), C00P(H00P), C00S(H00S)
5.d Idealised Me refined as rotating group:
 C00X(H00C,H00D,H00L), C00Z(H00M,H00O,H00Q), C010(H01A,H01B,H01C), C011(H01D,
 H01E,H01F), C012(H01G,H01H,H01I), C013(H01J,H01K,H01L), C014(H01M,H01N,H01O),
 C015(H01P,H01Q,H01R), C016(H01S,H01T,H01U), C017(H01V,H01W,H01X), C018(H01Y,H,
 HA), C019(H01Z,HB,HC), C01E(H0AA,HE,HF), C01E(HG,HH,HI), C2(H2A,H2B,H2C)
5.e Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_shelx_res_checksum              69472
_shelx_fab_checksum              45780
_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 2.422
_oxdiff_exptl_absorpt_empirical_full_min 0.715