#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/66/4506629.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_4506629
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         'C12 H13 N3 O4, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C18 H15 N5 O4'
_chemical_formula_weight         365.35
_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                 105.7932(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8021(2)
_cell_length_b                   19.8646(6)
_cell_length_c                   11.9355(4)
_cell_measurement_reflns_used    18468
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.77
_cell_volume                     1780.00(9)
_computing_cell_refinement       'Denzo-SMN (Otwinowsi & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowsi & 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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18468
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.0547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                2032
_reflns_number_total             3493
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (7)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4506629
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7905(3) 0.16099(9) -0.24462(14) 0.0827(6) Uani 1 1 d . A .
O2 O 0.685(2) 0.2539(6) -0.3429(6) 0.111(4) Uani 0.69(6) 1 d PD A 1
C9 C 0.688(6) 0.2179(9) -0.4497(11) 0.131(7) Uani 0.69(6) 1 d PD A 1
H9A H 0.8087 0.2081 -0.4485 0.196 Uiso 0.69(6) 1 calc PR A 1
H9B H 0.6340 0.2454 -0.5161 0.196 Uiso 0.69(6) 1 calc PR A 1
H9C H 0.6224 0.1765 -0.4543 0.196 Uiso 0.69(6) 1 calc PR A 1
O2' O 0.656(4) 0.2468(12) -0.3456(13) 0.090(6) Uani 0.31(6) 1 d PD A 2
C9' C 0.602(7) 0.2055(18) -0.450(2) 0.124(11) Uani 0.31(6) 1 d PD A 2
H9'1 H 0.7045 0.1826 -0.4613 0.186 Uiso 0.31(6) 1 calc PR A 2
H9'2 H 0.5508 0.2335 -0.5157 0.186 Uiso 0.31(6) 1 calc PR A 2
H9'3 H 0.5160 0.1730 -0.4407 0.186 Uiso 0.31(6) 1 calc PR A 2
O3 O 0.8056(3) 0.36197(8) -0.20770(14) 0.0786(5) Uani 1 1 d . A .
O4 O 0.5116(2) 0.07533(8) 0.42332(12) 0.0612(4) Uani 1 1 d . . .
N1 N 0.7220(2) 0.16181(10) -0.03600(15) 0.0496(5) Uani 1 1 d . . .
N2 N 0.7223(2) 0.22795(8) -0.04665(13) 0.0450(4) Uani 1 1 d . . .
N3 N 0.5625(3) -0.02756(10) 0.36396(18) 0.0547(5) Uani 1 1 d . . .
C1 C 0.6859(2) 0.13265(10) 0.06281(15) 0.0420(5) Uani 1 1 d . . .
C2 C 0.6831(3) 0.06335(11) 0.06951(18) 0.0512(5) Uani 1 1 d . . .
C3 C 0.6418(3) 0.03226(12) 0.16218(17) 0.0491(5) Uani 1 1 d . . .
C4 C 0.6034(2) 0.06992(9) 0.25037(15) 0.0394(4) Uani 1 1 d . . .
C5 C 0.6081(3) 0.13946(11) 0.24212(18) 0.0511(5) Uani 1 1 d . . .
C6 C 0.6493(3) 0.17115(11) 0.14982(18) 0.0525(6) Uani 1 1 d . . .
C7 C 0.7374(3) 0.25698(10) -0.14187(16) 0.0457(5) Uani 1 1 d . A .
C8 C 0.7419(3) 0.21867(12) -0.24666(18) 0.0573(6) Uani 1 1 d D . .
C10 C 0.7498(3) 0.33138(11) -0.13584(18) 0.0518(5) Uani 1 1 d . . .
C11 C 0.7015(5) 0.36752(17) -0.0386(3) 0.0654(7) Uani 1 1 d . A .
C12 C 0.5561(2) 0.03929(10) 0.35209(16) 0.0433(5) Uani 1 1 d . . .
H1N H 0.735(3) 0.1354(12) -0.092(2) 0.063(7) Uiso 1 1 d . . .
H3N1 H 0.591(3) -0.0530(12) 0.314(2) 0.066(7) Uiso 1 1 d . . .
H3N2 H 0.531(3) -0.0437(12) 0.428(2) 0.073(7) Uiso 1 1 d . . .
H2 H 0.714(3) 0.0383(13) 0.014(2) 0.081(8) Uiso 1 1 d . . .
H3 H 0.644(3) -0.0150(12) 0.1664(18) 0.062(6) Uiso 1 1 d . . .
H5 H 0.579(3) 0.1656(11) 0.2979(18) 0.055(6) Uiso 1 1 d . . .
H6 H 0.654(3) 0.2178(12) 0.1475(18) 0.060(6) Uiso 1 1 d . . .
H111 H 0.622(5) 0.345(2) -0.020(3) 0.137(15) Uiso 1 1 d . . .
H112 H 0.641(5) 0.405(2) -0.061(3) 0.138(15) Uiso 1 1 d . . .
H113 H 0.797(6) 0.393(2) -0.001(4) 0.158(16) Uiso 1 1 d . . .
C1A C 1.0510(2) 0.03037(11) 0.40719(16) 0.0457(5) Uani 1 1 d . . .
C2A C 1.0132(3) 0.07016(12) 0.49865(18) 0.0532(5) Uani 1 1 d . . .
C3A C 0.9642(3) 0.04134(12) 0.58669(18) 0.0527(6) Uani 1 1 d . . .
C4A C 1.0989(3) 0.06054(11) 0.31686(16) 0.0506(5) Uani 1 1 d . . .
C5A C 1.1317(3) 0.02170(12) 0.22311(19) 0.0577(6) Uani 1 1 d . . .
C6A C 1.1178(3) 0.13156(14) 0.30907(19) 0.0645(6) Uani 1 1 d . . .
N1A N 1.1566(3) -0.00897(12) 0.14887(18) 0.0789(7) Uani 1 1 d . . .
N2A N 1.1334(4) 0.18858(13) 0.3037(2) 0.1011(8) Uani 1 1 d . . .
H2A H 1.021(3) 0.1186(13) 0.4944(18) 0.065(7) Uiso 1 1 d . . .
H3A H 0.938(3) 0.0694(12) 0.6480(19) 0.065(6) 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
C8 O2 C9 114.7(10) . .
C8 O2' C9' 119(2) . .
O2' C9' H9'1 109.5 . .
O2' C9' H9'2 109.5 . .
H9'1 C9' H9'2 109.5 . .
O2' C9' H9'3 109.5 . .
H9'1 C9' H9'3 109.5 . .
H9'2 C9' H9'3 109.5 . .
N2 N1 C1 119.71(17) . .
N2 N1 H1N 121.4(15) . .
C1 N1 H1N 118.7(15) . .
C7 N2 N1 121.70(17) . .
C12 N3 H3N1 121.3(16) . .
C12 N3 H3N2 115.1(15) . .
H3N1 N3 H3N2 124(2) . .
C2 C1 C6 119.96(19) . .
C2 C1 N1 117.94(18) . .
C6 C1 N1 122.08(18) . .
C3 C2 C1 120.3(2) . .
C3 C2 H2 120.4(16) . .
C1 C2 H2 119.3(16) . .
C2 C3 C4 120.8(2) . .
C2 C3 H3 119.0(13) . .
C4 C3 H3 120.1(13) . .
C5 C4 C3 117.88(18) . .
C5 C4 C12 118.80(17) . .
C3 C4 C12 123.32(18) . .
C6 C5 C4 121.8(2) . .
C6 C5 H5 118.6(13) . .
C4 C5 H5 119.5(13) . .
C5 C6 C1 119.2(2) . .
C5 C6 H6 120.0(14) . .
C1 C6 H6 120.8(14) . .
N2 C7 C8 122.59(18) . .
N2 C7 C10 114.70(17) . .
C8 C7 C10 122.71(17) . .
O1 C8 O2' 120.3(10) . .
O1 C8 O2 123.6(5) . .
O2' C8 O2 11(2) . .
O1 C8 C7 123.67(19) . .
O2' C8 C7 114.8(9) . .
O2 C8 C7 112.7(5) . .
O3 C10 C7 119.50(19) . .
O3 C10 C11 121.2(2) . .
C7 C10 C11 119.2(2) . .
C10 C11 H111 107(3) . .
C10 C11 H112 113(2) . .
H111 C11 H112 99(3) . .
C10 C11 H113 107(3) . .
H111 C11 H113 137(4) . .
H112 C11 H113 89(3) . .
O4 C12 N3 120.97(19) . .
O4 C12 C4 120.23(18) . .
N3 C12 C4 118.80(18) . .
C4A C1A C3A 121.25(19) . 3_756
C4A C1A C2A 120.8(2) . .
C3A C1A C2A 118.00(19) 3_756 .
C3A C2A C1A 121.4(2) . .
C3A C2A H2A 120.0(13) . .
C1A C2A H2A 118.6(13) . .
C2A C3A C1A 120.6(2) . 3_756
C2A C3A H3A 120.1(13) . .
C1A C3A H3A 119.3(13) 3_756 .
C1A C4A C6A 122.65(19) . .
C1A C4A C5A 121.4(2) . .
C6A C4A C5A 115.93(19) . .
N1A C5A C4A 179.6(3) . .
N2A C6A C4A 179.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.205(3) .
O2 C8 1.315(7) .
O2 C9 1.468(8) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
O2' C8 1.314(11) .
O2' C9' 1.452(15) .
C9' H9'1 0.9600 .
C9' H9'2 0.9600 .
C9' H9'3 0.9600 .
O3 C10 1.223(2) .
O4 C12 1.231(2) .
N1 N2 1.320(2) .
N1 C1 1.410(2) .
N1 H1N 0.87(2) .
N2 C7 1.308(2) .
N3 C12 1.335(3) .
N3 H3N1 0.86(2) .
N3 H3N2 0.92(3) .
C1 C2 1.380(3) .
C1 C6 1.381(3) .
C2 C3 1.379(3) .
C2 H2 0.91(3) .
C3 C4 1.389(3) .
C3 H3 0.94(2) .
C4 C5 1.386(3) .
C4 C12 1.491(3) .
C5 C6 1.381(3) .
C5 H5 0.92(2) .
C6 H6 0.93(2) .
C7 C8 1.473(3) .
C7 C10 1.482(3) .
C10 C11 1.498(3) .
C11 H111 0.85(4) .
C11 H112 0.88(4) .
C11 H113 0.91(5) .
C1A C4A 1.371(3) .
C1A C3A 1.433(3) 3_756
C1A C2A 1.442(3) .
C2A C3A 1.340(3) .
C2A H2A 0.97(2) .
C3A C1A 1.433(3) 3_756
C3A H3A 0.98(2) .
C4A C6A 1.424(3) .
C4A C5A 1.438(3) .
C5A N1A 1.135(3) .
C6A N2A 1.143(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146177
