#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/66/4506628.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_4506628
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         'C17 H14 N2 O2, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C23 H16 N4 O2'
_chemical_formula_weight         380.40
_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                76.4040(10)
_cell_angle_beta                 76.3821(10)
_cell_angle_gamma                85.9155(9)
_cell_formula_units_Z            2
_cell_length_a                   7.7738(2)
_cell_length_b                   10.0484(2)
_cell_length_c                   12.6865(2)
_cell_measurement_reflns_used    14042
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      3.89
_cell_volume                     936.02(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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14042
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0454
_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)+(0.0593P)²+0.1352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                4132
_reflns_number_total             5393
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg3004382_si_002.cif
_cod_data_source_block           (6)
_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               4506628
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
_atom_site_refinement_flags
C1 C 0.24071(14) -0.04923(11) 0.39557(8) 0.0397(2) Uani 1 1 d .
C2 C 0.29449(15) 0.07238(11) 0.41254(8) 0.0414(2) Uani 1 1 d .
C3 C 0.38187(16) 0.14449(12) 0.30372(9) 0.0459(3) Uani 1 1 d .
C4 C 0.26345(16) 0.09349(12) 0.52385(9) 0.0436(2) Uani 1 1 d .
C5 C 0.4799(2) 0.27549(16) 0.26748(12) 0.0688(4) Uani 1 1 d .
H5A H 0.5570 0.2798 0.1955 0.083 Uiso 1 1 calc R
H5B H 0.5487 0.2800 0.3202 0.083 Uiso 1 1 calc R
H5C H 0.3971 0.3511 0.2633 0.083 Uiso 1 1 calc R
O1 O 0.16186(12) -0.15458(8) 0.47011(6) 0.0500(2) Uani 1 1 d .
O2 O 0.21124(15) -0.00446(9) 0.60402(7) 0.0627(3) Uani 1 1 d .
N1 N 0.28635(12) -0.04456(9) 0.28528(7) 0.0408(2) Uani 1 1 d .
N2 N 0.37716(14) 0.07525(10) 0.22832(8) 0.0472(2) Uani 1 1 d .
C6 C 0.27873(15) -0.14724(11) 0.22634(8) 0.0405(2) Uani 1 1 d .
C7 C 0.39162(18) -0.13646(14) 0.12194(9) 0.0519(3) Uani 1 1 d .
C8 C 0.3876(2) -0.23498(17) 0.06270(11) 0.0635(4) Uani 1 1 d .
C9 C 0.2756(2) -0.34416(16) 0.10692(13) 0.0654(4) Uani 1 1 d .
C10 C 0.1635(2) -0.35468(14) 0.21073(12) 0.0590(3) Uani 1 1 d .
C11 C 0.16288(17) -0.25532(12) 0.27095(10) 0.0474(3) Uani 1 1 d .
C12 C 0.28472(14) 0.22821(12) 0.54760(8) 0.0412(2) Uani 1 1 d .
C13 C 0.22005(17) 0.34782(13) 0.48840(10) 0.0481(3) Uani 1 1 d .
C14 C 0.22737(19) 0.47042(14) 0.51920(12) 0.0574(3) Uani 1 1 d .
C15 C 0.30127(19) 0.47401(15) 0.60758(13) 0.0604(3) Uani 1 1 d .
C16 C 0.36785(18) 0.35591(15) 0.66581(11) 0.0568(3) Uani 1 1 d .
C17 C 0.35733(16) 0.23285(14) 0.63719(10) 0.0481(3) Uani 1 1 d .
H1 H 0.157(3) -0.126(2) 0.5405(18) 0.099(6) Uiso 1 1 d .
H7 H 0.475(2) -0.0610(17) 0.0934(13) 0.064(4) Uiso 1 1 d .
H8 H 0.472(2) -0.2298(19) -0.0094(16) 0.089(6) Uiso 1 1 d .
H9 H 0.274(2) -0.4166(18) 0.0671(14) 0.077(5) Uiso 1 1 d .
H10 H 0.079(2) -0.4325(18) 0.2425(13) 0.070(5) Uiso 1 1 d .
H11 H 0.081(2) -0.2618(16) 0.3457(13) 0.064(4) Uiso 1 1 d .
H13 H 0.163(2) 0.3423(16) 0.4278(13) 0.061(4) Uiso 1 1 d .
H14 H 0.180(2) 0.5540(18) 0.4779(14) 0.073(5) Uiso 1 1 d .
H15 H 0.311(2) 0.561(2) 0.6253(15) 0.083(5) Uiso 1 1 d .
H16 H 0.427(2) 0.3589(16) 0.7292(13) 0.067(4) Uiso 1 1 d .
H17 H 0.397(2) 0.1465(16) 0.6837(12) 0.060(4) Uiso 1 1 d .
C1A C 0.03216(15) 0.11883(11) 0.03364(9) 0.0418(2) Uani 1 1 d .
C2A C 0.09256(17) 0.10717(12) -0.08073(9) 0.0461(3) Uani 1 1 d .
C3A C -0.06188(17) 0.00587(12) 0.11296(9) 0.0456(3) Uani 1 1 d .
C4A C 0.06371(16) 0.23582(12) 0.06465(9) 0.0454(2) Uani 1 1 d .
C5A C 0.01252(18) 0.25204(13) 0.17705(10) 0.0507(3) Uani 1 1 d .
C6A C 0.14897(19) 0.35159(13) -0.01465(11) 0.0551(3) Uani 1 1 d .
N1A N -0.02468(19) 0.26868(13) 0.26578(10) 0.0681(3) Uani 1 1 d .
N2A N 0.2150(2) 0.44560(14) -0.07683(11) 0.0788(4) Uani 1 1 d .
H2A H 0.157(2) 0.1852(16) -0.1376(13) 0.061(4) Uiso 1 1 d .
H3A H -0.1054(18) 0.0124(15) 0.1917(12) 0.052(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
O1 C1 N1 123.37(10) .
O1 C1 C2 128.64(9) .
N1 C1 C2 107.98(9) .
C1 C2 C3 104.22(9) .
C1 C2 C4 119.52(10) .
C3 C2 C4 136.15(10) .
N2 C3 C2 111.07(10) .
N2 C3 C5 118.43(10) .
C2 C3 C5 130.40(11) .
O2 C4 C2 118.86(10) .
O2 C4 C12 118.34(9) .
C2 C4 C12 122.76(10) .
C3 C5 H5A 109.5 .
C3 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C3 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C1 O1 H1 101.1(12) .
C1 N1 N2 110.34(8) .
C1 N1 C6 130.20(9) .
N2 N1 C6 118.71(8) .
C3 N2 N1 106.32(9) .
C11 C6 C7 120.62(10) .
C11 C6 N1 121.38(9) .
C7 C6 N1 118.00(10) .
C8 C7 C6 119.33(12) .
C8 C7 H7 121.6(9) .
C6 C7 H7 119.0(9) .
C9 C8 C7 120.62(13) .
C9 C8 H8 120.1(11) .
C7 C8 H8 119.1(11) .
C8 C9 C10 119.93(12) .
C8 C9 H9 121.8(10) .
C10 C9 H9 118.3(10) .
C9 C10 C11 120.43(13) .
C9 C10 H10 120.3(9) .
C11 C10 H10 119.2(9) .
C6 C11 C10 119.03(12) .
C6 C11 H11 120.1(9) .
C10 C11 H11 120.9(9) .
C13 C12 C17 119.60(11) .
C13 C12 C4 121.13(10) .
C17 C12 C4 119.04(11) .
C14 C13 C12 119.78(12) .
C14 C13 H13 121.3(9) .
C12 C13 H13 118.8(9) .
C15 C14 C13 120.11(13) .
C15 C14 H14 120.6(10) .
C13 C14 H14 119.3(10) .
C16 C15 C14 120.40(12) .
C16 C15 H15 120.5(11) .
C14 C15 H15 119.0(11) .
C15 C16 C17 119.79(12) .
C15 C16 H16 120.6(9) .
C17 C16 H16 119.6(9) .
C16 C17 C12 120.29(12) .
C16 C17 H17 119.3(8) .
C12 C17 H17 120.4(8) .
C4A C1A C3A 121.46(10) .
C4A C1A C2A 120.39(10) .
C3A C1A C2A 118.16(10) .
C3A C2A C1A 121.32(11) 2
C3A C2A H2A 119.2(9) 2
C1A C2A H2A 119.5(9) .
C2A C3A C1A 120.52(10) 2
C2A C3A H3A 120.1(8) 2
C1A C3A H3A 119.3(8) .
C1A C4A C6A 121.89(10) .
C1A C4A C5A 123.13(11) .
C6A C4A C5A 114.97(10) .
N1A C5A C4A 177.70(15) .
N2A C6A C4A 178.70(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.3189(13) .
C1 N1 1.3503(13) .
C1 C2 1.3976(15) .
C2 C3 1.4319(15) .
C2 C4 1.4389(14) .
C3 N2 1.3165(14) .
C3 C5 1.4894(17) .
C4 O2 1.2489(14) .
C4 C12 1.4825(15) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
O1 H1 1.00(2) .
N1 N2 1.3935(13) .
N1 C6 1.4211(13) .
C6 C11 1.3861(16) .
C6 C7 1.3910(15) .
C7 C8 1.3825(18) .
C7 H7 0.977(16) .
C8 C9 1.376(2) .
C8 H8 0.986(19) .
C9 C10 1.383(2) .
C9 H9 0.981(18) .
C10 C11 1.3915(17) .
C10 H10 1.001(17) .
C11 H11 1.000(16) .
C12 C13 1.3888(17) .
C12 C17 1.3940(16) .
C13 C14 1.3858(18) .
C13 H13 0.989(16) .
C14 C15 1.383(2) .
C14 H14 0.978(18) .
C15 C16 1.379(2) .
C15 H15 0.966(19) .
C16 C17 1.3810(18) .
C16 H16 1.023(16) .
C17 H17 1.001(16) .
C1A C4A 1.3787(15) .
C1A C3A 1.4389(16) .
C1A C2A 1.4460(15) .
C2A C3A 1.3479(16) 2
C2A H2A 1.002(16) .
C3A C2A 1.3479(16) 2
C3A H3A 0.992(14) .
C4A C6A 1.4319(17) .
C4A C5A 1.4322(16) .
C5A N1A 1.1432(16) .
C6A N2A 1.1428(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146176
