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#$Date: 2019-12-26 21:49:16 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/19/2021921.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021921
loop_
_publ_author_name
'Shukla, Rahul'
'Ruzié, Christian'
'Schweicher, Guillaume'
'Kennedy, Alan R.'
'Geerts, Yves H.'
'Chopra, Deepak'
'Chattopadhyay, Basab'
_publ_section_title
;
 Insight from electron density and energy framework analysis on the
 structural features of F  x  -TCNQ (x = 0, 2, 4) family of
 molecules
;
_journal_coeditor_code           AW5018SUP1
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first              71
_journal_paper_doi               10.1107/S2052520618017109
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         'C12 H2 F2 N4'
_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   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.969(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1713(19)
_cell_length_b                   5.8670(12)
_cell_length_c                   8.8512(17)
_cell_measurement_reflns_used    3976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.41
_cell_volume                     505.20(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_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            8822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_min         2.406
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.7467
_exptl_transmission_factor_min   0.6920
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0469
_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)+(0.0384P)²+0.6736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                688
_reflns_number_total             849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5018sup1.cif
_cod_data_source_block           F2-TCNQ
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2021921
_shelx_shelxl_version_number     2014/7
_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.
;
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
F1 F 0.76125(11) 0.5000 0.97938(13) 0.0191(3) Uani 1 2 d S T P
N1 N 0.33218(17) 0.5000 0.44923(19) 0.0196(4) Uani 1 2 d S T P
N2 N 0.02227(18) 0.5000 0.6963(2) 0.0235(4) Uani 1 2 d S T P
C5 C 0.52791(19) 0.5000 0.8524(2) 0.0143(4) Uani 1 2 d DS T P
C6 C 0.63140(17) 0.5000 0.9873(2) 0.0138(4) Uani 1 2 d S T P
C2 C 0.13778(19) 0.5000 0.7091(2) 0.0163(4) Uani 1 2 d S T P
C4 C 0.38735(18) 0.5000 0.8568(2) 0.0135(4) Uani 1 2 d S T P
C1 C 0.30968(19) 0.5000 0.5689(2) 0.0155(4) Uani 1 2 d S T P
C3 C 0.28096(19) 0.5000 0.7187(2) 0.0148(4) Uani 1 2 d S T P
H5 H 0.549(2) 0.5000 0.7394(12) 0.017(6) Uiso 1 2 d DS . 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_3
C6 C5 C4 120.14(15) .
C6 C5 H5 120.4(11) .
C4 C5 H5 119.4(11) .
C5 C6 F1 118.77(15) .
C5 C6 C4 124.14(16) 5_667
F1 C6 C4 117.08(15) 5_667
N2 C2 C3 177.9(2) .
C3 C4 C5 120.32(16) .
C3 C4 C6 123.97(16) 5_667
C5 C4 C6 115.71(16) 5_667
N1 C1 C3 179.8(2) .
C4 C3 C2 125.10(16) .
C4 C3 C1 120.01(16) .
C2 C3 C1 114.89(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C6 1.3430(19) .
N1 C1 1.147(2) .
N2 C2 1.147(3) .
C5 C6 1.342(2) .
C5 C4 1.442(2) .
C5 H5 1.0828(11) .
C6 C4 1.447(2) 5_667
C2 C3 1.434(3) .
C4 C3 1.376(3) .
C4 C6 1.447(2) 5_667
C1 C3 1.439(3) .
