#------------------------------------------------------------------------------
#$Date: 2025-07-06 15:32:35 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300520 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134655.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_7134655
loop_
_publ_author_name
'Suo, Meng-Ting'
'Fleege, Jouke A.'
'Yutronkie, Nathan J.'
'Nadurata, Vincent L.'
'Chernyshov, Dmitry'
'Rouzières, Mathieu'
'Mailman, Aaron'
'Clérac, Rodolphe'
'Dechambenoit, Pierre'
_publ_section_title
;
 Syntheses and characterisation of terephthalonitrile radical salts
;
_journal_issue                   54
_journal_name_full               'Chemical Communications'
_journal_page_first              9972
_journal_page_last               9975
_journal_paper_doi               10.1039/D5CC02417J
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H20 Li N2 O2'
_chemical_formula_sum            'C16 H20 Li N2 O2'
_chemical_formula_weight         279.28
_chemical_properties_physical    Moisture-sensitive
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-05-26 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.844(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.939(4)
_cell_length_b                   5.9609(16)
_cell_length_c                   18.837(4)
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.79
_cell_volume                     1641.7(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5322
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.146
_diffrn_reflns_theta_max         24.146
_diffrn_reflns_theta_min         2.786
_diffrn_source                   'Incoatec microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0703
_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)+(0.1501P)²+0.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                811
_reflns_number_total             1281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc02417j2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134654--7134656.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7134655
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.997
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 0.55599(18) 0.3592(4) 0.68729(11) 0.0813(10) Uani 1 1 d . . . . .
N1 N 0.4056(2) 0.0081(5) 0.67727(15) 0.0808(11) Uani 1 1 d . . . . .
C2 C 0.2916(3) -0.0457(6) 0.49693(18) 0.0739(12) Uani 1 1 d . . . . .
H2 H 0.320192 0.093787 0.494543 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3061(2) -0.1615(5) 0.56304(15) 0.0546(9) Uani 1 1 d . . . . .
C4 C 0.3606(2) -0.0698(6) 0.62568(17) 0.0631(10) Uani 1 1 d . . . . .
C5 C 0.5266(4) 0.3925(9) 0.6120(2) 0.1073(18) Uani 1 1 d . . . . .
H5A H 0.460129 0.413953 0.600044 0.129 Uiso 1 1 calc R U . . .
H5B H 0.541647 0.260883 0.585581 0.129 Uiso 1 1 calc R U . . .
C6 C 0.5727(3) 0.5917(8) 0.5911(2) 0.0931(14) Uani 1 1 d . . . . .
H6A H 0.528001 0.707411 0.571087 0.112 Uiso 1 1 calc R U . . .
H6B H 0.608495 0.553229 0.554675 0.112 Uiso 1 1 calc R U . . .
C7 C 0.6340(3) 0.6725(9) 0.6596(2) 0.0996(15) Uani 1 1 d . . . . .
H7A H 0.696055 0.698893 0.651869 0.119 Uiso 1 1 calc R U . . .
H7B H 0.610557 0.812167 0.676284 0.119 Uiso 1 1 calc R U . . .
C1 C 0.2377(3) -0.1300(6) 0.43684(17) 0.0808(13) Uani 1 1 d . . . . .
H1 H 0.229159 -0.047138 0.393518 0.097 Uiso 1 1 calc R U . . .
C8 C 0.6337(4) 0.4950(10) 0.7116(3) 0.129(2) Uani 1 1 d . . . . .
H8A H 0.689468 0.404889 0.716319 0.155 Uiso 1 1 calc R U . . .
H8B H 0.631704 0.558839 0.759221 0.155 Uiso 1 1 calc R U . . .
Li1 Li 0.500000 0.1695(13) 0.750000 0.061(2) Uani 1 2 d S T P . .
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'
Li Li -0.0003 0.0001 '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
C5 O1 C8 108.2(3) . . ?
C5 O1 Li1 127.5(2) . . ?
C8 O1 Li1 124.3(2) . . ?
C4 N1 Li1 166.7(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 C1 122.3(3) . 7_546 ?
C2 C3 C1 116.7(3) . 7_546 ?
N1 C4 C3 179.4(4) . . ?
O1 C5 C6 108.5(3) . . ?
O1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 C7 105.5(3) . . ?
C5 C6 H6A 110.6 . . ?
C7 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
C7 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C6 105.2(4) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C2 C1 C3 121.9(3) . 7_546 ?
C2 C1 H1 119.1 . . ?
C3 C1 H1 119.1 7_546 . ?
O1 C8 C7 108.5(3) . . ?
O1 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O1 Li1 O1 108.8(4) 2_656 . ?
O1 Li1 N1 101.21(11) 2_656 2_656 ?
O1 Li1 N1 111.44(13) . 2_656 ?
O1 Li1 N1 111.44(13) 2_656 . ?
O1 Li1 N1 101.21(11) . . ?
N1 Li1 N1 122.5(4) 2_656 . ?
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 C5 1.410(4) . ?
O1 C8 1.412(5) . ?
O1 Li1 1.944(5) . ?
N1 C4 1.160(4) . ?
N1 Li1 1.999(5) . ?
C2 C1 1.345(4) . ?
C2 C3 1.401(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.400(4) . ?
C3 C1 1.405(5) 7_546 ?
C5 C6 1.467(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.500(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.443(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C1 H1 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
