#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:53:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179602 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/66/4506623.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_4506623
loop_
_publ_author_name
'Bertolasi, Valerio'
'Gilli, Paola'
'Gilli, Gastone'
_publ_section_title
;
 Adducts of TCNQ with Neutral Nitrogen Bases. Their Rationalization in
 Terms of Intermolecular Charge-Transfer (CT) or Electron
 Donor--Acceptor (EDA) Interactions
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4758
_journal_paper_doi               10.1021/cg3004382
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C4 H5 N3, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C10 H7 N5'
_chemical_formula_weight         197.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.0121(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4818(2)
_cell_length_b                   18.7663(7)
_cell_length_c                   7.8072(3)
_cell_measurement_reflns_used    7797
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.06
_cell_volume                     1001.31(6)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7797
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.0590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1495
_reflns_number_total             2171
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (1)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4506623
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.54677(19) 0.00896(7) 0.77051(18) 0.0564(3) Uani 1 1 d
N2 N 0.43203(17) -0.08704(6) 0.87866(15) 0.0552(3) Uani 1 1 d
N3 N 0.44766(17) -0.08905(6) 0.57837(14) 0.0546(3) Uani 1 1 d
C1 C 0.47306(18) -0.05757(7) 0.74161(16) 0.0466(3) Uani 1 1 d
C2 C 0.3595(2) -0.15278(9) 0.8454(2) 0.0633(4) Uani 1 1 d
C3 C 0.3304(3) -0.19008(9) 0.6853(2) 0.0688(4) Uani 1 1 d
C4 C 0.3776(2) -0.15524(8) 0.5543(2) 0.0628(4) Uani 1 1 d
H1N H 0.556(2) 0.0326(8) 0.671(2) 0.063(4) Uiso 1 1 d
H2N H 0.554(2) 0.0340(8) 0.879(2) 0.072(4) Uiso 1 1 d
H2 H 0.331(2) -0.1732(8) 0.943(2) 0.072(4) Uiso 1 1 d
H3 H 0.276(3) -0.2398(9) 0.667(2) 0.082(5) Uiso 1 1 d
H4 H 0.362(2) -0.1776(8) 0.432(2) 0.068(4) Uiso 1 1 d
C1A C 0.06749(19) 0.05829(9) 0.6255(2) 0.0581(4) Uani 1 1 d
C2A C 0.1019(2) 0.05492(10) 0.4572(2) 0.0627(4) Uani 1 1 d
C3A C 0.0386(2) 0.00000(9) 0.3392(2) 0.0625(4) Uani 1 1 d
C4A C 0.1341(2) 0.11412(8) 0.7477(2) 0.0614(4) Uani 1 1 d
C5A C 0.0914(2) 0.12162(9) 0.9103(2) 0.0707(5) Uani 1 1 d
C6A C 0.2561(2) 0.16885(9) 0.7243(2) 0.0652(4) Uani 1 1 d
N1A N 0.0569(3) 0.12863(10) 1.0390(2) 0.0969(5) Uani 1 1 d
N2A N 0.3589(2) 0.21089(9) 0.7095(2) 0.0816(4) Uani 1 1 d
H2A H 0.164(2) 0.0919(9) 0.428(2) 0.072(5) Uiso 1 1 d
H3A H 0.060(2) -0.0013(8) 0.229(3) 0.070(5) Uiso 1 1 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
_geom_angle_site_symmetry_3
C1 N1 H1N 118.1(9) . .
C1 N1 H2N 118.6(9) . .
H1N N1 H2N 121.3(14) . .
C2 N2 C1 115.66(12) . .
C4 N3 C1 116.02(11) . .
N3 C1 N2 125.60(13) . .
N3 C1 N1 117.13(11) . .
N2 C1 N1 117.27(12) . .
N2 C2 C3 123.51(14) . .
N2 C2 H2 115.1(10) . .
C3 C2 H2 121.3(10) . .
C2 C3 C4 116.21(15) . .
C2 C3 H3 120.7(10) . .
C4 C3 H3 123.1(10) . .
N3 C4 C3 122.98(14) . .
N3 C4 H4 114.2(9) . .
C3 C4 H4 122.8(9) . .
C4A C1A C2A 121.36(14) . .
C4A C1A C3A 121.40(14) . 3_556
C2A C1A C3A 117.24(15) . 3_556
C3A C2A C1A 121.26(15) . .
C3A C2A H2A 119.4(10) . .
C1A C2A H2A 119.3(10) . .
C2A C3A C1A 121.50(14) . 3_556
C2A C3A H3A 120.5(10) . .
C1A C3A H3A 118.0(10) 3_556 .
C1A C4A C6A 122.04(13) . .
C1A C4A C5A 122.85(14) . .
C6A C4A C5A 115.10(15) . .
N1A C5A C4A 178.98(19) . .
N2A C6A C4A 177.47(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3462(18) .
N1 H1N 0.923(16) .
N1 H2N 0.952(17) .
N2 C2 1.330(2) .
N2 C1 1.3462(16) .
N3 C4 1.3317(19) .
N3 C1 1.3462(16) .
C2 C3 1.371(2) .
C2 H2 0.953(16) .
C3 C4 1.375(2) .
C3 H3 1.004(17) .
C4 H4 1.008(16) .
C1A C4A 1.367(2) .
C1A C2A 1.440(2) .
C1A C3A 1.442(2) 3_556
C2A C3A 1.334(2) .
C2A H2A 0.912(16) .
C3A C1A 1.442(2) 3_556
C3A H3A 0.938(18) .
C4A C6A 1.434(2) .
C4A C5A 1.437(2) .
C5A N1A 1.143(2) .
C6A N2A 1.140(2) .
