#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/66/4506627.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_4506627
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         'C7 H6 N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C13 H8 N4 O'
_chemical_formula_weight         236.23
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.0993(12)
_cell_angle_beta                 81.4628(13)
_cell_angle_gamma                63.8558(15)
_cell_formula_units_Z            2
_cell_length_a                   7.7288(2)
_cell_length_b                   8.6397(3)
_cell_length_c                   9.7439(3)
_cell_measurement_reflns_used    6955
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.04
_cell_volume                     561.44(3)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6955
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0417
_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)+(0.0508P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                1904
_reflns_number_total             2524
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (5)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4506627
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 1.04617(14) 0.19645(12) 0.51186(10) 0.0584(3) Uani 1 1 d
C1 C 0.96299(17) 0.24035(15) 0.38764(13) 0.0447(3) Uani 1 1 d
N1 N 0.91599(17) 0.13204(13) 0.34451(12) 0.0533(3) Uani 1 1 d
N2 N 0.83163(17) 0.22543(15) 0.21450(12) 0.0536(3) Uani 1 1 d
C2 C 0.82829(16) 0.38984(16) 0.17714(13) 0.0440(3) Uani 1 1 d
C3 C 0.91304(15) 0.40588(15) 0.28692(12) 0.0416(3) Uani 1 1 d
C4 C 0.93073(18) 0.56298(17) 0.27884(15) 0.0492(3) Uani 1 1 d
C5 C 0.86299(19) 0.69818(18) 0.16026(16) 0.0573(4) Uani 1 1 d
C6 C 0.7771(2) 0.68121(19) 0.05141(16) 0.0597(4) Uani 1 1 d
C7 C 0.75676(19) 0.52991(18) 0.05695(14) 0.0545(3) Uani 1 1 d
H1O H 1.062(3) 0.071(3) 0.566(2) 0.111(7) Uiso 1 1 d
H2 H 0.799(2) 0.168(2) 0.166(2) 0.088(6) Uiso 1 1 d
H4 H 0.990(2) 0.5750(19) 0.3566(17) 0.064(4) Uiso 1 1 d
H5 H 0.869(2) 0.813(2) 0.1494(17) 0.069(4) Uiso 1 1 d
H6 H 0.727(2) 0.780(2) -0.0319(19) 0.073(4) Uiso 1 1 d
H7 H 0.695(2) 0.518(2) -0.0201(18) 0.069(4) Uiso 1 1 d
C1A C 0.44825(15) 0.65853(15) 0.39205(12) 0.0401(3) Uani 1 1 d
C2A C 0.41265(17) 0.51323(16) 0.37831(13) 0.0431(3) Uani 1 1 d
C3A C 0.46125(17) 0.36322(16) 0.48063(13) 0.0435(3) Uani 1 1 d
C4A C 0.39825(17) 0.81275(16) 0.28702(13) 0.0438(3) Uani 1 1 d
C5A C 0.43705(19) 0.95764(17) 0.29527(14) 0.0526(3) Uani 1 1 d
N1A N 0.4674(2) 1.07473(18) 0.29678(16) 0.0782(4) Uani 1 1 d
C6A C 0.30974(18) 0.83770(16) 0.15886(14) 0.0489(3) Uani 1 1 d
N2A N 0.24191(19) 0.85781(16) 0.05527(13) 0.0667(4) Uani 1 1 d
H2A H 0.3502(18) 0.5246(17) 0.2962(15) 0.052(3) Uiso 1 1 d
H3A H 0.4357(19) 0.2713(18) 0.4690(15) 0.053(4) 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'
O O 0.0106 0.0060 '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 O1 H1O 109.4(12) . .
N1 C1 O1 123.08(11) . .
N1 C1 C3 111.64(11) . .
O1 C1 C3 125.28(11) . .
C1 N1 N2 105.75(10) . .
C2 N2 N1 111.11(11) . .
C2 N2 H2 130.7(12) . .
N1 N2 H2 117.9(12) . .
N2 C2 C3 107.21(11) . .
N2 C2 C7 131.40(12) . .
C3 C2 C7 121.38(12) . .
C2 C3 C4 120.67(11) . .
C2 C3 C1 104.27(10) . .
C4 C3 C1 135.06(12) . .
C5 C4 C3 117.60(13) . .
C5 C4 H4 121.5(9) . .
C3 C4 H4 120.9(9) . .
C4 C5 C6 121.28(13) . .
C4 C5 H5 121.4(9) . .
C6 C5 H5 117.3(9) . .
C7 C6 C5 122.37(13) . .
C7 C6 H6 117.1(10) . .
C5 C6 H6 120.5(10) . .
C6 C7 C2 116.70(13) . .
C6 C7 H7 122.6(9) . .
C2 C7 H7 120.7(9) . .
C4A C1A C2A 121.15(11) . .
C4A C1A C3A 120.98(11) . 2_666
C2A C1A C3A 117.87(10) . 2_666
C3A C2A C1A 121.11(11) . .
C3A C2A H2A 119.0(8) . .
C1A C2A H2A 119.8(8) . .
C2A C3A C1A 121.02(11) . 2_666
C2A C3A H3A 119.2(8) . .
C1A C3A H3A 119.8(8) 2_666 .
C1A C4A C6A 122.27(11) . .
C1A C4A C5A 122.57(11) . .
C6A C4A C5A 115.12(11) . .
N1A C5A C4A 177.61(14) . .
N2A C6A C4A 178.80(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3367(15) .
O1 H1O 1.03(2) .
C1 N1 1.3208(16) .
C1 C3 1.4193(17) .
N1 N2 1.3793(15) .
N2 C2 1.3557(17) .
N2 H2 0.897(19) .
C2 C3 1.4006(17) .
C2 C7 1.4027(18) .
C3 C4 1.4031(17) .
C4 C5 1.3692(19) .
C4 H4 0.990(16) .
C5 C6 1.402(2) .
C5 H5 0.991(16) .
C6 C7 1.370(2) .
C6 H6 0.979(17) .
C7 H7 1.000(17) .
C1A C4A 1.3742(17) .
C1A C2A 1.4412(16) .
C1A C3A 1.4415(16) 2_666
C2A C3A 1.3375(17) .
C2A H2A 0.955(15) .
C3A C1A 1.4415(16) 2_666
C3A H3A 0.936(14) .
C4A C6A 1.4318(17) .
C4A C5A 1.4341(18) .
C5A N1A 1.1390(17) .
C6A N2A 1.1422(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146175
