#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:23:49 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038046.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_4038046
loop_
_publ_author_name
'Liu, En-Chih'
'Topczewski, Joseph J.'
_publ_section_title
;
 Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane
 (F₂-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/[σ²(Fo²)+(0.0489P)²+0.3303P] where P=(Fo²+2Fc²)/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 > 2σ(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_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
F1 F 0.76170(8) 0.500000 0.97970(10) 0.0185(2) Uani 1 2 d S T P . .
N1 N 0.02182(13) 0.500000 0.69593(15) 0.0224(3) Uani 1 2 d S T P . .
C1 C 0.13756(14) 0.500000 0.70889(16) 0.0164(3) Uani 1 2 d S T P . .
N2 N 0.33246(13) 0.500000 0.44927(15) 0.0196(3) Uani 1 2 d S T P . .
C2 C 0.30960(14) 0.500000 0.56894(17) 0.0158(3) Uani 1 2 d S T P . .
C3 C 0.28101(13) 0.500000 0.71863(16) 0.0147(3) Uani 1 2 d S T P . .
C4 C 0.38746(13) 0.500000 0.85676(16) 0.0137(3) Uani 1 2 d S T P . .
C5 C 0.52812(13) 0.500000 0.85252(15) 0.0144(3) Uani 1 2 d S T P . .
H5 H 0.548030 0.500000 0.753549 0.017 Uiso 1 2 calc R U P . .
C6 C 0.63143(13) 0.500000 0.98760(16) 0.0142(3) 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'
F F 0.0171 0.0103 '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'
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
N1 C1 C3 177.81(14) . . ?
N2 C2 C3 179.99(15) . . ?
C4 C3 C2 120.14(15) . . ?
C4 C3 C1 125.25(14) . . ?
C2 C3 C1 114.61(14) . . ?
C3 C4 C5 120.53(14) . . ?
C3 C4 C6 124.00(14) . 5_667 ?
C5 C4 C6 115.47(13) . 5_667 ?
C6 C5 C4 120.24(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 F1 118.82(14) . . ?
C5 C6 C4 124.29(14) . 5_667 ?
F1 C6 C4 116.89(13) . 5_667 ?
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
F1 C6 1.340(2) . ?
N1 C1 1.144(2) . ?
C1 C3 1.430(3) . ?
N2 C2 1.143(2) . ?
C2 C3 1.430(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.435(2) . ?
C4 C6 1.438(2) 5_667 ?
C5 C6 1.339(2) . ?
C5 H5 0.9500 . ?
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 C3 C4 C5 0.000(1) . . . . ?
C1 C3 C4 C5 180.000(0) . . . . ?
C2 C3 C4 C6 180.000(1) . . . 5_667 ?
C1 C3 C4 C6 0.000(1) . . . 5_667 ?
C3 C4 C5 C6 180.000(1) . . . . ?
C6 C4 C5 C6 0.000(1) 5_667 . . . ?
C4 C5 C6 F1 180.000(0) . . . . ?
C4 C5 C6 C4 0.000(1) . . . 5_667 ?
