Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane (F<sub>2</sub>-TCNQ).
Liu, En-Chih; Topczewski, Joseph J.; The Journal of organic chemistry 85 (2020) 4560–4564; doi:10.1021/acs.joc.0c00053

data_4038046
_publ_section_title
;
 Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane
 (F<sub>2</sub>-TCNQ).
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4560
_journal_page_last               4564
_journal_paper_doi               10.1021/acs.joc.0c00053
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C12 H2 F2 N4'
_chemical_formula_weight         240.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.72(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.122(13)
_cell_length_b                   5.827(5)
_cell_length_c                   8.812(11)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.41
_cell_volume                     497.8(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker_Photon_II_CMOS
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9654
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.629
_diffrn_reflns_theta_min         2.413
_exptl_absorpt_coefficient_mu    0.129
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0489P)^2^+0.3303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                713
_reflns_number_total             841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00053_si_001.cif
_cod_data_source_block           19084z_a
_cod_depositor_comments          'Adding full bibliography for 4038046.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               4038046
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              50854
_shelx_hkl_checksum              15545