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#$Date: 2020-12-04 04:22:25 +0200 (Fri, 04 Dec 2020) $
#$Revision: 259524 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135368.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_4135368
loop_
_publ_author_name
'Kasemthaveechok, Sitthichok'
'Abella, Laura'
'Jean, Marion'
'Cordier, Marie'
'Roisnel, Thierry'
'Vanthuyne, Nicolas'
'Guizouarn, Thierry'
'Cador, Olivier'
'Autschbach, Jochen'
'Crassous, Jeanne'
'Favereau, Ludovic'
_publ_section_title
;
 Axially and Helically Chiral Cationic Radical Bicarbazoles: SOMO-HOMO
 Level Inversion and Chirality Impact on the Stability of Mono- and
 Diradical Cations.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20409
_journal_page_last               20418
_journal_paper_doi               10.1021/jacs.0c08948
_journal_volume                  142
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H20 N2 O2'
_chemical_formula_sum            'C27 H20 N2 O2'
_chemical_formula_weight         404.45
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.302(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.408(2)
_cell_length_b                   18.225(2)
_cell_length_c                   7.9041(11)
_cell_measurement_reflns_used    7819
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4806
_cell_measurement_theta_min      3.0472
_cell_measurement_wavelength     0.71073
_cell_volume                     1926.0(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.047
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0572
_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)+(0.0912P)²+1.7207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             2216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0c08948_si_003.cif
_cod_data_source_block           SCK121
_cod_depositor_comments
'Adding full bibliography for 4135368--4135371.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4135368
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
O1 O 0.02742(11) 0.07333(7) 0.11153(15) 0.0334(4) Uani 1 1 d . . . . .
N1 N 0.27584(10) 0.30399(9) 0.30019(18) 0.0279(4) Uani 1 1 d . . . . .
C1 C 0.000000 0.03001(14) 0.250000 0.0394(7) Uani 1 2 d S T P . .
H1A H 0.056886 -0.001978 0.288679 0.047 Uiso 0.5 1 calc R U P . .
H1B H -0.056887 -0.001978 0.211323 0.047 Uiso 0.5 1 calc R U P . .
C2 C 0.09269(14) 0.13066(9) 0.1589(2) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.19259(15) 0.12536(11) 0.1214(2) 0.0329(5) Uani 1 1 d . . . . .
H3 H 0.215116 0.082279 0.068375 0.040 Uiso 1 1 calc R U . . .
C4 C 0.25863(14) 0.18138(11) 0.1601(2) 0.0323(4) Uani 1 1 d . . . . .
H4 H 0.326147 0.178435 0.131838 0.039 Uiso 1 1 calc R U . . .
C5 C 0.22332(12) 0.24301(10) 0.2424(2) 0.0244(4) Uani 1 1 d . . . . .
C6 C 0.12198(11) 0.24922(9) 0.28188(19) 0.0197(4) Uani 1 1 d . . . . .
C7 C 0.05394(11) 0.19279(8) 0.23498(18) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.21229(12) 0.34970(9) 0.3811(2) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.23356(14) 0.41651(10) 0.4608(2) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.298119 0.438009 0.461012 0.038 Uiso 1 1 calc R U . . .
C10 C 0.15749(15) 0.45054(10) 0.5399(2) 0.0333(4) Uani 1 1 d . . . . .
H10 H 0.170024 0.496176 0.595572 0.040 Uiso 1 1 calc R U . . .
C11 C 0.06182(14) 0.41876(10) 0.5393(2) 0.0287(4) Uani 1 1 d . . . . .
H11 H 0.011098 0.442830 0.596148 0.034 Uiso 1 1 calc R U . . .
C12 C 0.04060(12) 0.35299(9) 0.4572(2) 0.0219(4) Uani 1 1 d . . . . .
H12 H -0.024350 0.332121 0.456661 0.026 Uiso 1 1 calc R U . . .
C13 C 0.11587(11) 0.31744(8) 0.37471(19) 0.0195(3) Uani 1 1 d . . . . .
C14 C 0.38234(13) 0.31551(13) 0.2908(3) 0.0377(5) Uani 1 1 d . . . . .
H14A H 0.418727 0.271328 0.330149 0.057 Uiso 1 1 calc R U . . .
H14B H 0.404065 0.357187 0.362728 0.057 Uiso 1 1 calc R U . . .
H14C H 0.396165 0.325790 0.173111 0.057 Uiso 1 1 calc R U . . .
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'
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
C2 O1 C1 113.76(12) . . ?
C5 N1 C8 108.82(13) . . ?
C5 N1 C14 125.55(16) . . ?
C8 N1 C14 125.43(17) . . ?
O1 C1 O1 112.4(2) . 2 ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1A 109.1 2 . ?
O1 C1 H1B 109.1 . . ?
O1 C1 H1B 109.1 2 . ?
H1A C1 H1B 107.8 . . ?
O1 C2 C3 118.91(15) . . ?
O1 C2 C7 118.36(16) . . ?
C3 C2 C7 122.66(17) . . ?
C4 C3 C2 121.00(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 117.80(16) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 128.38(16) . . ?
N1 C5 C6 109.69(15) . . ?
C4 C5 C6 121.92(17) . . ?
C7 C6 C5 119.73(15) . . ?
C7 C6 C13 134.50(14) . . ?
C5 C6 C13 105.71(14) . . ?
C2 C7 C6 116.77(15) . . ?
C2 C7 C7 117.81(12) . 2 ?
C6 C7 C7 125.38(11) . 2 ?
N1 C8 C9 128.67(16) . . ?
N1 C8 C13 109.01(15) . . ?
C9 C8 C13 122.32(16) . . ?
C10 C9 C8 117.68(16) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 121.15(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.91(17) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.31(15) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C8 118.60(15) . . ?
C12 C13 C6 134.63(14) . . ?
C8 C13 C6 106.73(14) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
O1 C2 1.396(2) . ?
O1 C1 1.4202(19) . ?
N1 C5 1.375(2) . ?
N1 C8 1.382(2) . ?
N1 C14 1.451(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.397(3) . ?
C2 C7 1.400(2) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(2) . ?
C6 C7 1.406(2) . ?
C6 C13 1.449(2) . ?
C7 C7 1.483(3) 2 ?
C8 C9 1.391(3) . ?
C8 C13 1.418(2) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 O1 46.41(10) . . . 2 ?
C1 O1 C2 C3 107.27(17) . . . . ?
C1 O1 C2 C7 -75.71(18) . . . . ?
O1 C2 C3 C4 177.69(15) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C8 N1 C5 C4 -177.08(16) . . . . ?
C14 N1 C5 C4 -1.9(3) . . . . ?
C8 N1 C5 C6 1.53(18) . . . . ?
C14 N1 C5 C6 176.66(14) . . . . ?
C3 C4 C5 N1 176.86(15) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
N1 C5 C6 C7 -179.86(13) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
N1 C5 C6 C13 -2.17(17) . . . . ?
C4 C5 C6 C13 176.55(14) . . . . ?
O1 C2 C7 C6 179.62(13) . . . . ?
C3 C2 C7 C6 -3.5(2) . . . . ?
O1 C2 C7 C7 1.7(2) . . . 2 ?
C3 C2 C7 C7 178.61(16) . . . 2 ?
C5 C6 C7 C2 3.6(2) . . . . ?
C13 C6 C7 C2 -173.32(16) . . . . ?
C5 C6 C7 C7 -178.72(16) . . . 2 ?
C13 C6 C7 C7 4.4(3) . . . 2 ?
C5 N1 C8 C9 178.85(16) . . . . ?
C14 N1 C8 C9 3.7(3) . . . . ?
C5 N1 C8 C13 -0.23(18) . . . . ?
C14 N1 C8 C13 -175.37(14) . . . . ?
N1 C8 C9 C10 -177.12(16) . . . . ?
C13 C8 C9 C10 1.8(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C8 1.1(2) . . . . ?
C11 C12 C13 C6 178.30(16) . . . . ?
N1 C8 C13 C12 176.78(13) . . . . ?
C9 C8 C13 C12 -2.4(2) . . . . ?
N1 C8 C13 C6 -1.11(17) . . . . ?
C9 C8 C13 C6 179.74(14) . . . . ?
C7 C6 C13 C12 1.8(3) . . . . ?
C5 C6 C13 C12 -175.43(17) . . . . ?
C7 C6 C13 C8 179.16(16) . . . . ?
C5 C6 C13 C8 1.97(16) . . . . ?
