#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/37/7213764.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_7213764
loop_
_publ_author_name
'Dobrowolski, Michał A.'
'Garbarino, Gaston'
'Mezouar, Mohamed'
'Ciesielski, Arkadiusz'
'Cyrański, Michał K.'
_publ_section_title
;
 Structural diversities of charge transfer organic complexes. Focus on
 benzenoid hydrocarbons and 7,7,8,8-tetracyanoquinodimethane
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              415
_journal_paper_doi               10.1039/c3ce41703d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H4 N4, C14 H10'
_chemical_formula_sum            'C26 H14 N4'
_chemical_formula_weight         382.41
_chemical_name_systematic
; 
 Phenanthrene-7,7,8,8-tetracyanoquinodimethane complex
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.212(16)
_cell_angle_beta                 97.720(15)
_cell_angle_gamma                99.521(12)
_cell_formula_units_Z            1
_cell_length_a                   6.7083(9)
_cell_length_b                   8.0897(12)
_cell_length_c                   9.118(2)
_cell_measurement_temperature    100(2)
_cell_volume                     471.54(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4006
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0761
_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)+(0.1137P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.2282
_reflns_number_gt                1799
_reflns_number_total             4006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41703d.txt
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        471.55(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213764
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9030(13) -0.1312(14) 0.6329(10) 0.0195(16) Uani 0.50 1 d PDU A -1
H1 H 0.8918 -0.1012 0.5368 0.023 Uiso 0.50 1 calc PR A -1
C2 C 0.8673(12) -0.3015(19) 0.6405(16) 0.020(3) Uani 0.50 1 d PD A -1
H2 H 0.8308 -0.3878 0.5492 0.024 Uiso 0.50 1 calc PR A -1
C3 C 0.8835(12) -0.3490(17) 0.779(2) 0.023(3) Uani 0.50 1 d PD A -1
H3 H 0.8581 -0.4672 0.7818 0.027 Uiso 0.50 1 calc PR A -1
C4 C 0.9383(14) -0.2210(11) 0.9157(10) 0.0165(16) Uani 0.50 1 d PDU A -1
C5 C 0.9750(15) -0.0465(14) 0.9070(12) 0.014(2) Uani 0.50 1 d PD A -1
C6 C 0.9550(16) -0.0040(14) 0.7639(12) 0.016(2) Uani 0.50 1 d PD A -1
H6 H 0.9776 0.1133 0.7576 0.019 Uiso 0.50 1 calc PR A -1
C7 C 0.9538(8) -0.2693(8) 1.0598(7) 0.0224(15) Uani 0.50 1 d PD A -1
H7 H 0.9277 -0.3876 1.0629 0.027 Uiso 0.50 1 calc PR A -1
C8 C 1.0041(8) -0.1510(7) 1.1883(7) 0.0203(15) Uani 0.50 1 d PD A -1
H8 H 1.0124 -0.1864 1.2820 0.024 Uiso 0.50 1 calc PR A -1
C9 C 1.0469(16) 0.0317(13) 1.1899(12) 0.016(2) Uani 0.50 1 d PD A -1
C10 C 1.0313(16) 0.0846(13) 1.0515(13) 0.014(2) Uani 0.50 1 d PD A -1
C11 C 1.1024(13) 0.1582(14) 1.3288(10) 0.0195(16) Uani 0.50 1 d PDU A -1
H11 H 1.1153 0.1235 1.4228 0.023 Uiso 0.50 1 calc PR A -1
C12 C 1.1373(13) 0.331(2) 1.3272(16) 0.020(3) Uani 0.50 1 d PD A -1
H12 H 1.1720 0.4139 1.4204 0.024 Uiso 0.50 1 calc PR A -1
C13 C 1.1226(14) 0.3834(17) 1.193(2) 0.023(3) Uani 0.50 1 d PD A -1
H13 H 1.1468 0.5027 1.1934 0.027 Uiso 0.50 1 calc PR A -1
C14 C 1.0724(14) 0.2631(11) 1.0550(11) 0.0165(16) Uani 0.50 1 d PDU A -1
H14 H 1.0655 0.3011 0.9625 0.020 Uiso 0.50 1 calc PR A -1
N2X N 0.3457(5) 0.4186(4) 0.7473(3) 0.0421(9) Uani 1 1 d . . .
N4X N 0.3475(4) 0.7960(3) 0.4649(3) 0.0303(8) Uani 1 1 d . . .
C3X C 0.4711(4) 0.8277(4) 1.0147(3) 0.0165(7) Uani 1 1 d . . .
H3X H 0.4517 0.7108 1.0222 0.020 Uiso 1 1 calc R . .
C5X C 0.4482(4) 0.8683(4) 0.8664(3) 0.0148(7) Uani 1 1 d . . .
C7X C 0.4806(4) 1.0473(4) 0.8578(3) 0.0156(7) Uani 1 1 d . . .
H7X H 0.4678 1.0767 0.7616 0.019 Uiso 1 1 calc R . .
C8X C 0.3985(4) 0.7399(4) 0.7366(3) 0.0177(7) Uani 1 1 d . . .
C9X C 0.3717(4) 0.7724(4) 0.5851(4) 0.0201(8) Uani 1 1 d . . .
C10X C 0.3684(5) 0.5606(5) 0.7425(3) 0.0249(8) Uani 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 0.0000 '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 0.0000 '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
C2 C1 C6 120.3(9) .
C1 C2 C3 121.1(11) .
C2 C3 C4 119.9(10) .
C5 C4 C3 118.6(8) .
C5 C4 C7 121.1(8) .
C3 C4 C7 120.3(9) .
C6 C5 C4 119.5(9) .
C6 C5 C10 122.9(8) .
C4 C5 C10 117.6(7) .
C1 C6 C5 120.5(9) .
C8 C7 C4 120.8(6) .
C7 C8 C9 121.8(6) .
C10 C9 C11 119.3(9) .
C10 C9 C8 119.2(8) .
C11 C9 C8 121.4(8) .
C9 C10 C14 118.5(9) .
C9 C10 C5 119.5(7) .
C14 C10 C5 122.0(7) .
C12 C11 C9 120.3(9) .
C13 C12 C11 120.8(11) .
C12 C13 C14 120.4(11) .
C13 C14 C10 120.7(9) .
C7X C3X C5X 121.1(3) 2_677
C8X C5X C3X 120.8(3) .
C8X C5X C7X 120.8(3) .
C3X C5X C7X 118.4(2) .
C3X C7X C5X 120.4(3) 2_677
C5X C8X C10X 121.7(3) .
C5X C8X C9X 123.4(3) .
C10X C8X C9X 114.9(3) .
N4X C9X C8X 178.8(3) .
N2X C10X C8X 179.6(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.375(16) .
C1 C6 1.378(14) .
C2 C3 1.383(16) .
C3 C4 1.421(16) .
C4 C5 1.411(11) .
C4 C7 1.438(9) .
C5 C6 1.408(11) .
C5 C10 1.481(6) .
C7 C8 1.324(8) .
C8 C9 1.455(10) .
C9 C10 1.406(11) .
C9 C11 1.425(13) .
C10 C14 1.418(11) .
C11 C12 1.380(15) .
C12 C13 1.372(16) .
C13 C14 1.392(16) .
N2X C10X 1.144(4) .
N4X C9X 1.144(4) .
C3X C7X 1.347(4) 2_677
C3X C5X 1.446(4) .
C5X C8X 1.375(3) .
C5X C7X 1.447(4) .
C7X C3X 1.347(4) 2_677
C8X C10X 1.443(4) .
C8X C9X 1.450(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197984
