A remarkably air-stable quinodimethane radical cation.
Harada, Mei; Tanioka, Masaru; Muranaka, Atsuya; Aoyama, Tetsuya; Kamino, Shinichiro; Uchiyama, Masanobu; Chemical communications (Cambridge, England) 56 (2020) 9565–9568; doi:10.1039/d0cc04025h

data_7126873
_publ_section_title
;
 A remarkably air-stable quinodimethane radical cation.
;
_journal_issue                   66
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9565
_journal_page_last               9568
_journal_paper_doi               10.1039/d0cc04025h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'C H2 Cl2, C8 Cl2 N2 O2, 2(C25 H25 N O2), H2 O'
_chemical_formula_sum            'C59 H54 Cl4 N4 O7'
_chemical_formula_weight         1072.86
_chemical_name_common
'bridged-tetra-aryl-p-quinodimethane (BTAQ) radical cation'
_chemical_name_systematic        1?+?DDQ?--
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-01 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                114.686(3)
_cell_angle_beta                 94.742(2)
_cell_angle_gamma                99.943(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3092(2)
_cell_length_b                   18.6978(6)
_cell_length_c                   20.9767(5)
_cell_measurement_reflns_used    5725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6670
_cell_measurement_theta_min      2.3470
_cell_volume                     2527.02(14)
_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_temperature      293(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.957
_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    -69.00  41.00   0.50    6.00    --  -39.95  38.00-151.00  220
  2  \w      8.00 121.00   0.50    6.00    --   39.95  38.00-151.00  226
  3  \w     81.00 178.00   0.50   33.00    --  109.49  38.00-151.00  194
  4  \w     80.00 106.00   0.50   33.00    --  109.49 -94.00-120.00   52
  5  \w     90.00 116.00   0.50   33.00    --  109.49-125.00-180.00   52
  6  \w     61.00 108.00   0.50   33.00    --  109.49 -94.00 -60.00   94
  7  \w     72.00  98.00   0.50   33.00    --  109.49 -94.00 -30.00   52
  8  \w     45.00 108.00   0.50   33.00    --  109.49 -94.00  30.00  126
  9  \w     77.00 117.00   0.50   33.00    --  109.49-125.00  90.00   80
 10  \w     62.00  89.00   0.50   33.00    --  109.49 -94.00 150.00   54
 11  \w     70.00 106.00   0.50   33.00    --  109.49 -94.00  90.00   72
 12  \w     40.00  66.00   0.50   33.00    --  109.49 -38.00  53.00   52
 13  \w     30.00  59.00   0.50   33.00    --  109.49 -94.00 -30.00   58
 14  \w     32.00  77.00   0.50   33.00    --  109.49 -45.00 -60.00   90
 15  \w     50.00  76.00   0.50   33.00    --  109.49 -45.00-120.00   52
 16  \w     34.00  64.00   0.50   33.00    --  109.49 -30.00-150.00   60
 17  \w     34.00  60.00   0.50   33.00    --  109.49 -30.00-120.00   52
 18  \w     31.00  78.00   0.50   33.00    --  109.49 -45.00-150.00   94
 19  \w     36.00 104.00   0.50   33.00    --  109.49 -94.00-150.00  136
 20  \w     37.00  63.00   0.50   33.00    --  109.49 -94.00-120.00   52
 21  \w     32.00  57.00   0.50   33.00    --  109.49-125.00-180.00   50
 22  \w     34.00  66.00   0.50   33.00    --  109.49 -45.00-180.00   64
 23  \w     80.00 177.00   0.50   33.00    --  109.49  45.00-180.00  194
 24  \w     41.00 123.00   0.50    6.00    --   39.95 178.00  30.00  164
 25  \w     75.00 161.00   0.50   33.00    --  109.49  77.00 120.00  172
 26  \w     83.00 169.00   0.50   33.00    --  109.49  45.00  90.00  172
 27  \w     82.00 129.00   0.50   33.00    --  109.49  61.00  90.00   94
 28  \w     31.00  60.00   0.50   33.00    --  109.49 -45.00 -30.00   58
 29  \w     45.00  71.00   0.50   33.00    --  109.49-125.00  90.00   52
 30  \w     33.00  59.00   0.50   33.00    --  109.49 -94.00 150.00   52
 31  \w    -41.00  72.00   0.50    6.00    --   39.95 -38.00  53.00  226
 32  \w    -37.00 -11.00   0.50   33.00    --  -84.50  30.00  30.00   52
 33  \w    -58.00 -12.00   0.50   33.00    --  -84.50 125.00 -90.00   92
 34  \w    -69.00  -3.00   0.50   33.00    --  -84.50  38.00-151.00  132
 35  \w   -121.00  -8.00   0.50    6.00    --  -39.95 -38.00  53.00  226
 36  \w   -109.00 -40.00   0.50   33.00    --  -84.50  77.00 120.00  138
 37  \w   -116.00 -67.00   0.50   33.00    --  -84.50 125.00 -90.00   98
 38  \w   -165.00 -68.00   0.50   33.00    --  -84.50 -38.00  53.00  194
 39  \w   -124.00 -71.00   0.50    6.00    --  -39.95-178.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0827130000
_diffrn_orient_matrix_UB_12      -0.0901752000
_diffrn_orient_matrix_UB_13      -0.0219988000
_diffrn_orient_matrix_UB_21      -0.1753251000
_diffrn_orient_matrix_UB_22      0.0213878000
_diffrn_orient_matrix_UB_23      0.0329838000
_diffrn_orient_matrix_UB_31      -0.0980589000
_diffrn_orient_matrix_UB_32      -0.0093886000
_diffrn_orient_matrix_UB_33      -0.0718542000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28290
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.455
_diffrn_reflns_theta_min         2.672
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    2.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49670
_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            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/diethyl ether'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     801
_refine_ls_number_reflns         9876
_refine_ls_number_restraints     588
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0758
_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^)+(0.0930P)^2^+3.1672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.1997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7390
_reflns_number_total             9876
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 3.5368\% 
 around [-0.29 0.93 -0.24] (reciprocal) or [-0.87 0.50 0.05] (direct)
Component 3 rotated by 176.3108\% 
 around [0.01 0.88 -0.48] (reciprocal) or [0.45 0.89 -0.03] (direct)
;
_cod_data_source_file            d0cc04025h2.cif
_cod_data_source_block           exp_219_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7126873--7126874.cif.'
_cod_database_code               7126873
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_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 O(H,H) groups
2. Restrained distances
 C01D-C00F = C01B-C00M
 1.51 with sigma of 0.0001
 Cl02-C01J \\sim Cl-C1AA
 with sigma of 0.02
 Cl03-C016 \\sim Cl1-C0
 with sigma of 0.02
 O009-C01M \\sim O0-C01N
 with sigma of 0.02
 O00B-C01C \\sim O00C-C2AA
 with sigma of 0.02
 C00F-C01D \\sim C5AA-C3AA
 with sigma of 0.02
 C00F-N1 \\sim C5AA-N1A
 with sigma of 0.02
 C00M-C01B \\sim C4AA-C0AA
 with sigma of 0.02
 C00M-N01N \\sim C4AA-N01O
 with sigma of 0.02
 C016-C01C \\sim C0-C2AA
 with sigma of 0.02
 C016-C01J \\sim C0-C1AA
 with sigma of 0.02
 C01B-C01D \\sim C0AA-C3AA
 with sigma of 0.02
 C01B-C01M \\sim C0AA-C01N
 with sigma of 0.02
 C01C-C01D \\sim C2AA-C3AA
 with sigma of 0.02
 C01J-C01M \\sim C1AA-C01N
 with sigma of 0.02
 Cl02-C016 \\sim Cl-C0
 with sigma of 0.04
 Cl02-C01M \\sim Cl-C01N
 with sigma of 0.04
 Cl03-C01C \\sim Cl1-C2AA
 with sigma of 0.04
 Cl03-C01J \\sim Cl1-C1AA
 with sigma of 0.04
 O009-C01B \\sim O0-C0AA
 with sigma of 0.04
 O009-C01J \\sim O0-C1AA
 with sigma of 0.04
 O00B-C016 \\sim O00C-C0
 with sigma of 0.04
 O00B-C01D \\sim O00C-C3AA
 with sigma of 0.04
 C00F-C01B \\sim C5AA-C0AA
 with sigma of 0.04
 C00F-C01C \\sim C5AA-C2AA
 with sigma of 0.04
 C00M-C01D \\sim C4AA-C3AA
 with sigma of 0.04
 C00M-C01M \\sim C4AA-C01N
 with sigma of 0.04
 C016-C01D \\sim C0-C3AA
 with sigma of 0.04
 C016-C01M \\sim C0-C01N
 with sigma of 0.04
 C01B-C01C \\sim C0AA-C2AA
 with sigma of 0.04
 C01B-C01J \\sim C0AA-C1AA
 with sigma of 0.04
 C01B-N01N \\sim C0AA-N01O
 with sigma of 0.04
 C01C-C01J \\sim C2AA-C1AA
 with sigma of 0.04
 C01D-C01M \\sim C3AA-C01N
 with sigma of 0.04
 C01D-N1 \\sim C3AA-N1A
 with sigma of 0.04
 O0-C1AA \\sim C0-O00C \\sim O00B-C016 \\sim O009-C01J
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O00C \\sim C0AA \\sim C01N \\sim C3AA \\sim C4AA \\sim C1AA \\sim O0 \\sim C2AA
\\sim C5AA \\sim N01O \\sim Cl \\sim C0 \\sim N1A \\sim Cl1 \\sim O00B \\sim
Cl02 \\sim C01J \\sim C016 \\sim C01M \\sim Cl03 \\sim C01C \\sim O009 \\sim
C01B \\sim C01D \\sim C00M \\sim C00F \\sim N01N \\sim N1: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O00C, C0AA, C01N, C3AA, C4AA, C1AA, O0, C2AA, C5AA, N01O, Cl, C0, N1A, Cl1,
 O00B, Cl02, C01J, C016, C01M, Cl03, C01C, O009, C01B, C01D, C00M, C00F, N01N,
 N1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C0AA)=Sof(Cl)=Sof(C1AA)=Sof(C0)=Sof(C01N)=Sof(Cl1)=Sof(C2AA)=Sof(O0)=
 Sof(O00C)=Sof(C3AA)=Sof(C4AA)=Sof(C5AA)=Sof(N01O)=Sof(N1A)=1-FVAR(1)
 Sof(Cl02)=Sof(Cl03)=Sof(O009)=Sof(O00B)=Sof(C00F)=Sof(C00M)=Sof(C016)=
 Sof(C01B)=Sof(C01C)=Sof(C01D)=Sof(C01J)=Sof(C01M)=Sof(N01N)=Sof(N1)=FVAR(1)
6.a Free rotating group:
 O00A(H00A,H00B)
6.b Secondary CH2 refined with riding coordinates:
 C01A(H01S,H01T), C01F(H01V,H01W), C01G(H01A,H01B), C01O(H01Y,H), C01P(H01Z,
 HA), C01Q(H01C,H01D), C01R(H01E,H01F), C01S(H01,HB), C01T(H01G,H01J),
 C01U(H01K,H01M), C01V(H0AA,HC), C01W(H2AA,HD), C01X(H01N,H01O)
6.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00O(H00O), C00W(H00W), C010(H010), C014(H014), C015(H015),
 C017(H017), C018(H018), C019(H019), C01E(H01U), C01H(H01H), C01I(H01I),
 C01K(H01X), C01L(H01L)
6.d Idealised Me refined as rotating group:
 C01Y(H01P,H01Q,H01R), C01Z(H1AA,HE,HF), C020(H02A,H02B,H02C), C021(H02D,H02E,
 H02F)
;
_shelx_res_checksum              76558
_shelx_hkl_checksum              95470
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.905
_oxdiff_exptl_absorpt_empirical_full_min 0.474
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3