Cyano modified triphenylmethyl radical skeletons: higher stability and efficiency.
Lv, Kuo; Zhang, Minzhe; Xia, Xin; Liu, Wenjing; Wan, Keke; Zhang, Ming; Li, Feng; Chemical communications (Cambridge, England) 60 (2024) 4846–4849; doi:10.1039/d4cc00903g

data_7132949
_publ_section_title
;
 Cyano modified triphenylmethyl radical skeletons: higher stability and
 efficiency.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4846
_journal_page_last               4849
_journal_paper_doi               10.1039/d4cc00903g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H6 Cl8 N1'
_chemical_formula_sum            'C20 H6 Cl8 N'
_chemical_formula_weight         543.86
_chemical_name_common            TTM-1CN
_chemical_name_systematic        BnBTM
_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     iterative
_audit_creation_date             2024-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-13 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.608(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0305(9)
_cell_length_b                   8.0731(5)
_cell_length_c                   18.9296(12)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.70
_cell_volume                     2137.2(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47418
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.700
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane?methanol'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0582
_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/[\s^2^(Fo^2^)+(0.0121P)^2^+11.0585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4235
_reflns_number_total             4910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00903g2.cif
_cod_data_source_block           httmcn
_cod_depositor_comments
'Adding full bibliography for 7132949--7132950.cif.'
_cod_database_code               7132949
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1-C2
 1.53 with sigma of 0.02
 N1-C1
 1.158 with sigma of 0.02
 C18-C22
 1.53 with sigma of 0.02
 N3-C22
 1.158 with sigma of 0.02
 C21-C12
 1.53 with sigma of 0.01
 N2-C21
 1.158 with sigma of 0.02
 C2-Cl9 \\sim C2-C1
 with sigma of 0.02
 C1-C3 \\sim C1-C7
 with sigma of 0.02
 Cl5-C18 \\sim C22-C18
 with sigma of 0.02
 Cl5-N3 \\sim C22-N3
 with sigma of 0.02
 C22-C17 \\sim C22-C19
 with sigma of 0.02
 C21-C11 \\sim C21-C13
 with sigma of 0.02
 N1-C3 \\sim N1-C7
 with sigma of 0.02
 N2-C11 \\sim N2-C13
 with sigma of 0.02
 N3-C17 \\sim N3-C19
 with sigma of 0.02
3. Restrained planarity
 C1, N1, C2, C3, C7
 with sigma of 0.01
 C21, N2, C11, C12, C13
 with sigma of 0.01
 C22, N3, C19, C17, C18
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim C1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C22 \\sim N3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Cl8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C21 \\sim N2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C22) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C21) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
Uanis(C1) = Uanis(C22) = Uanis(C21)
Uanis(N2) = Uanis(N1) = Uanis(N3)
5. Others
 Fixed Sof: Cl8(0.66667) Cl5(0.66667) Cl9(0.66667) N1(0.33333) C1(0.33333)
 N3(0.33333) N2(0.33333) C22(0.33333) C21(0.33333)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C19(H19), C13(H13), C17(H17), C7(H7), C3(H3)
;
_shelx_res_checksum              27295
_shelx_hkl_checksum              73415
_olex2_submission_special_instructions 'No special instructions were received'