#------------------------------------------------------------------------------
#$Date: 2019-12-26 21:49:16 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/19/2021919.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_2021919
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 H4 N4'
_chemical_formula_sum            'C12 H4 N4'
_chemical_formula_weight         204.19
_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   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.288(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8782(13)
_cell_length_b                   6.9117(10)
_cell_length_c                   16.398(2)
_cell_measurement_reflns_used    4041
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.51
_cell_volume                     995.7(2)
_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 0.999
_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  0.1026
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_min         2.510
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.6574
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0640P)²+0.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1097
_reflns_number_total             1519
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5018sup1.cif
_cod_data_source_block           TCNQ
_cod_original_cell_volume        995.8(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2021919
_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+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
N1 N 0.80648(12) 0.74384(16) 0.23996(6) 0.0237(3) Uani 1 1 d .
N2 N 0.47985(11) 0.93410(14) 0.40007(7) 0.0235(3) Uani 1 1 d .
C1 C 0.78636(12) 0.80879(15) 0.30193(7) 0.0164(3) Uani 1 1 d .
C3 C 0.76099(12) 0.88998(14) 0.37933(7) 0.0143(3) Uani 1 1 d .
C4 C 0.87937(12) 0.94389(14) 0.43884(7) 0.0132(3) Uani 1 1 d .
C6 C 0.84897(12) 1.02605(15) 0.51607(7) 0.0148(3) Uani 1 1 d D
C5 C 1.03554(12) 0.92036(15) 0.42576(7) 0.0143(3) Uani 1 1 d D
C2 C 0.60472(13) 0.91479(15) 0.39040(7) 0.0161(3) Uani 1 1 d .
H6 H 0.7321(5) 1.0408(18) 0.5269(8) 0.023(3) Uiso 1 1 d D
H5 H 1.0566(16) 0.8616(19) 0.3673(4) 0.031(4) Uiso 1 1 d D
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'
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
N1 C1 C3 179.92(14) .
C4 C3 C1 122.08(10) .
C4 C3 C2 122.03(10) .
C1 C3 C2 115.88(10) .
C3 C4 C5 121.02(10) .
C3 C4 C6 120.39(10) .
C5 C4 C6 118.59(10) .
C5 C6 C4 120.52(10) 5_776
C5 C6 H6 120.5(7) 5_776
C4 C6 H6 118.9(7) .
C6 C5 C4 120.89(10) 5_776
C6 C5 H5 121.3(8) 5_776
C4 C5 H5 117.8(8) .
N2 C2 C3 179.33(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.1482(15) .
N2 C2 1.1501(14) .
C1 C3 1.4349(16) .
C3 C4 1.3785(15) .
C3 C2 1.4352(16) .
C4 C5 1.4424(15) .
C4 C6 1.4484(16) .
C6 C5 1.3477(16) 5_776
C6 H6 1.0823(10) .
C5 C6 1.3477(16) 5_776
C5 H5 1.0824(10) .
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_4
C1 C3 C4 C5 -0.12(16) .
C2 C3 C4 C5 -179.00(10) .
C1 C3 C4 C6 179.76(10) .
C2 C3 C4 C6 0.88(15) .
C3 C4 C6 C5 -179.72(10) 5_776
C5 C4 C6 C5 0.17(17) 5_776
C3 C4 C5 C6 179.72(10) 5_776
C6 C4 C5 C6 -0.17(17) 5_776
