#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/66/4506630.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_4506630
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         'C16 H11 Cl N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C22 H13 Cl N4 O'
_chemical_formula_weight         384.81
_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                100.3045(17)
_cell_angle_beta                 94.3235(15)
_cell_angle_gamma                109.700(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0466(3)
_cell_length_b                   10.2842(4)
_cell_length_c                   11.7394(6)
_cell_measurement_reflns_used    15706
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.48
_cell_volume                     890.15(7)
_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      100
_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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15706
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.105
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0687
_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)+(0.1331P)²+0.3755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                3016
_reflns_number_total             3824
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (8)
_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               4506630
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 -0.1493(2) 0.17380(19) -0.01142(16) 0.0248(4) Uani 1 1 d
N1 N 0.2057(3) 0.1769(2) 0.04306(19) 0.0202(5) Uani 1 1 d
N2 N 0.1368(3) 0.1396(2) -0.06853(19) 0.0205(5) Uani 1 1 d
C1 C 0.1086(3) 0.2107(2) 0.1216(2) 0.0183(5) Uani 1 1 d
C2 C -0.0726(3) 0.2103(3) 0.0932(2) 0.0209(5) Uani 1 1 d
C3 C -0.1574(3) 0.2566(3) 0.1893(2) 0.0238(6) Uani 1 1 d
C4 C -0.0784(3) 0.2920(3) 0.2994(2) 0.0243(6) Uani 1 1 d
C5 C 0.0976(3) 0.2898(3) 0.3319(2) 0.0207(5) Uani 1 1 d
C6 C 0.1925(3) 0.2495(3) 0.2444(2) 0.0202(5) Uani 1 1 d
C7 C 0.3625(3) 0.2480(3) 0.2769(2) 0.0231(5) Uani 1 1 d
C8 C 0.4361(4) 0.2842(3) 0.3931(2) 0.0275(6) Uani 1 1 d
C9 C 0.3424(4) 0.3240(3) 0.4808(3) 0.0284(6) Uani 1 1 d
C10 C 0.1755(4) 0.3263(3) 0.4506(2) 0.0255(6) Uani 1 1 d
C11 C 0.2386(3) 0.1046(2) -0.1521(2) 0.0208(5) Uani 1 1 d
C12 C 0.4052(3) 0.0965(3) -0.1224(2) 0.0221(5) Uani 1 1 d
C13 C 0.5005(4) 0.0612(3) -0.2082(2) 0.0253(6) Uani 1 1 d
C14 C 0.4306(4) 0.0337(3) -0.3262(2) 0.0278(6) Uani 1 1 d
C15 C 0.2654(4) 0.0416(3) -0.3571(2) 0.0254(6) Uani 1 1 d
C16 C 0.1707(3) 0.0776(3) -0.2718(2) 0.0227(5) Uani 1 1 d
Cl1 Cl -0.03406(8) 0.09258(7) -0.31066(6) 0.0281(2) Uani 1 1 d
H1 H 0.022(4) 0.136(4) -0.088(3) 0.031(8) Uiso 1 1 d
H3 H -0.273(4) 0.263(3) 0.168(3) 0.025(7) Uiso 1 1 d
H4 H -0.147(5) 0.312(4) 0.357(3) 0.042(9) Uiso 1 1 d
H7 H 0.422(5) 0.213(4) 0.218(3) 0.040(9) Uiso 1 1 d
H8 H 0.555(4) 0.281(4) 0.410(3) 0.032(8) Uiso 1 1 d
H9 H 0.395(4) 0.353(4) 0.560(3) 0.039(9) Uiso 1 1 d
H10 H 0.112(4) 0.352(4) 0.509(3) 0.034(9) Uiso 1 1 d
H12 H 0.451(4) 0.118(3) -0.041(3) 0.030(8) Uiso 1 1 d
H13 H 0.620(4) 0.058(3) -0.185(3) 0.025(7) Uiso 1 1 d
H14 H 0.503(4) 0.008(4) -0.384(3) 0.032(8) Uiso 1 1 d
H15 H 0.216(4) 0.017(3) -0.435(3) 0.027(8) Uiso 1 1 d
N1A N 0.1998(3) 0.6822(3) 0.4078(2) 0.0281(5) Uani 1 1 d
N2A N 0.5683(3) 0.5710(2) 0.1916(2) 0.0256(5) Uani 1 1 d
C1A C 0.1291(3) 0.5458(2) 0.1018(2) 0.0177(5) Uani 1 1 d
C2A C 0.1700(3) 0.4936(3) -0.0114(2) 0.0181(5) Uani 1 1 d
C3A C 0.0477(3) 0.4496(2) -0.1080(2) 0.0184(5) Uani 1 1 d
C4A C 0.2554(3) 0.5863(2) 0.2003(2) 0.0190(5) Uani 1 1 d
C5A C 0.2218(3) 0.6392(3) 0.3146(2) 0.0211(5) Uani 1 1 d
C6A C 0.4291(3) 0.5782(3) 0.1947(2) 0.0195(5) Uani 1 1 d
H2A H 0.289(4) 0.496(3) -0.012(2) 0.013(6) Uiso 1 1 d
H3A H 0.072(3) 0.418(3) -0.186(2) 0.014(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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C1 118.6(2) . .
N1 N2 C11 119.1(2) . .
N1 N2 H1 118(2) . .
C11 N2 H1 123(2) . .
N1 C1 C6 115.9(2) . .
N1 C1 C2 124.5(2) . .
C6 C1 C2 119.6(2) . .
O1 C2 C3 121.6(2) . .
O1 C2 C1 120.8(2) . .
C3 C2 C1 117.5(2) . .
C4 C3 C2 121.6(2) . .
C4 C3 H3 122.4(18) . .
C2 C3 H3 115.9(18) . .
C3 C4 C5 122.8(2) . .
C3 C4 H4 116(2) . .
C5 C4 H4 121(2) . .
C6 C5 C10 119.4(2) . .
C6 C5 C4 119.8(2) . .
C10 C5 C4 120.8(2) . .
C7 C6 C5 119.3(2) . .
C7 C6 C1 122.2(2) . .
C5 C6 C1 118.5(2) . .
C8 C7 C6 120.5(2) . .
C8 C7 H7 120(2) . .
C6 C7 H7 119(2) . .
C7 C8 C9 120.7(3) . .
C7 C8 H8 117(2) . .
C9 C8 H8 122(2) . .
C10 C9 C8 119.7(3) . .
C10 C9 H9 120(2) . .
C8 C9 H9 121(2) . .
C9 C10 C5 120.5(3) . .
C9 C10 H10 120(2) . .
C5 C10 H10 119(2) . .
C12 C11 N2 122.9(2) . .
C12 C11 C16 118.4(2) . .
N2 C11 C16 118.7(2) . .
C13 C12 C11 120.7(2) . .
C13 C12 H12 121.7(19) . .
C11 C12 H12 117.5(19) . .
C12 C13 C14 120.0(3) . .
C12 C13 H13 119.4(18) . .
C14 C13 H13 120.5(18) . .
C15 C14 C13 119.9(3) . .
C15 C14 H14 123.1(19) . .
C13 C14 H14 117.0(19) . .
C16 C15 C14 120.1(3) . .
C16 C15 H15 119.9(19) . .
C14 C15 H15 119.9(19) . .
C15 C16 C11 120.8(2) . .
C15 C16 Cl1 120.1(2) . .
C11 C16 Cl1 119.10(19) . .
C4A C1A C3A 121.9(2) . 2_565
C4A C1A C2A 120.1(2) . .
C3A C1A C2A 117.9(2) 2_565 .
C3A C2A C1A 121.3(2) . .
C3A C2A H2A 123.5(17) . .
C1A C2A H2A 115.2(17) . .
C2A C3A C1A 120.8(2) . 2_565
C2A C3A H3A 123.4(15) . .
C1A C3A H3A 115.7(15) 2_565 .
C1A C4A C6A 122.0(2) . .
C1A C4A C5A 122.4(2) . .
C6A C4A C5A 115.7(2) . .
N1A C5A C4A 178.0(3) . .
N2A C6A C4A 179.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.263(3) .
N1 N2 1.318(3) .
N1 C1 1.325(3) .
N2 C11 1.399(3) .
N2 H1 0.92(3) .
C1 C6 1.470(3) .
C1 C2 1.470(3) .
C2 C3 1.452(4) .
C3 C4 1.326(4) .
C3 H3 0.97(3) .
C4 C5 1.447(4) .
C4 H4 0.94(4) .
C5 C6 1.410(4) .
C5 C10 1.414(4) .
C6 C7 1.398(4) .
C7 C8 1.378(4) .
C7 H7 0.95(4) .
C8 C9 1.404(4) .
C8 H8 0.97(3) .
C9 C10 1.372(4) .
C9 H9 0.94(4) .
C10 H10 0.93(3) .
C11 C12 1.393(4) .
C11 C16 1.412(4) .
C12 C13 1.382(4) .
C12 H12 0.95(3) .
C13 C14 1.397(4) .
C13 H13 0.99(3) .
C14 C15 1.384(4) .
C14 H14 0.98(3) .
C15 C16 1.376(4) .
C15 H15 0.92(3) .
C16 Cl1 1.741(3) .
N1A C5A 1.155(3) .
N2A C6A 1.150(3) .
C1A C4A 1.381(3) .
C1A C3A 1.446(3) 2_565
C1A C2A 1.447(3) .
C2A C3A 1.344(3) .
C2A H2A 0.95(3) .
C3A C1A 1.446(3) 2_565
C3A H3A 0.97(3) .
C4A C6A 1.433(3) .
C4A C5A 1.436(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146179
