#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/19/8101935.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_8101935
loop_
_publ_author_name
'McKay, S. E.'
'Wheeler, K. A.'
'Holthouse, B.'
_publ_section_title
;
Crystal structure of 2,2':6',2''-terpyridine 1,1''-dioxide 1,2,4,5-
tetracyanobenzene, C₁₅H₁₁N₃O₂ · C₆H₄(CN)₄
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              91
_journal_page_last               92
_journal_volume                  221
_journal_year                    2006
_chemical_formula_moiety         'C15 H11 N3 O2, C10 H2 N4'
_chemical_formula_sum            'C25 H13 N7 O2'
_chemical_formula_weight         443.42
_chemical_name_systematic
; 
 2,2':6',2"-terpyridine 1,1"-dioxide 1,2,4,5-tetracyanobenzene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.289(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.404(3)
_cell_length_b                   6.4871(11)
_cell_length_c                   13.4873(18)
_cell_measurement_reflns_used    443
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      49.327
_cell_measurement_theta_min      5.234
_cell_volume                     2027.3(5)
_computing_cell_refinement       'Rigaku Crystal Clear  v1.3 (Rigaku, 2004)'
_computing_data_collection       'Rigaku Crystal Clear  v1.3 (Rigaku, 2004)'
_computing_data_reduction        'Rigaku Crystal Clear  v1.3 (Rigaku, 2004)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku R-Axis Spider'
_diffrn_measurement_method       omega/phi
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6967
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0519P)²+1.1092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                1657
_reflns_number_total             1819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1731.cff
_cod_data_source_block           struct
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      C12/c1
_cod_database_code               8101935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O15 O 0.85259(4) 0.67640(16) 0.04289(8) 0.0218(3) Uani 1 8 f d . . .
N5 N 0.76274(5) 0.7180(2) 0.19765(9) 0.0205(3) Uani 1 8 f d . . .
N7 N 0.62168(5) 0.2753(2) -0.26980(9) 0.0241(3) Uani 1 8 f d . . .
N10 N 0.88152(5) 0.53075(18) 0.01446(8) 0.0141(3) Uani 1 8 f d . . .
N18 N 1.0000 0.4966(3) 0.2500 0.0133(4) Uani 1 4 e d S . .
C1 C 0.70617(6) 0.2556(2) -0.09581(10) 0.0147(3) Uani 1 8 f d . . .
C2 C 0.71228(6) 0.4188(2) -0.02602(10) 0.0153(3) Uani 1 8 f d . . .
C3 C 0.75612(5) 0.4140(2) 0.06981(10) 0.0144(3) Uani 1 8 f d . . .
C4 C 0.76072(5) 0.5835(2) 0.14141(10) 0.0159(3) Uani 1 8 f d . . .
C6 C 0.65964(6) 0.2633(2) -0.19351(10) 0.0166(3) Uani 1 8 f d . . .
C8 C 0.96575(5) 0.6043(2) 0.16892(9) 0.0138(3) Uani 1 8 f d . . .
C9 C 0.93605(5) 0.4780(2) 0.07606(9) 0.0134(3) Uani 1 8 f d . . .
C11 C 0.85588(6) 0.4263(2) -0.07620(10) 0.0170(3) Uani 1 8 f d . . .
C12 C 0.88237(6) 0.2615(2) -0.10575(11) 0.0176(3) Uani 1 8 f d . . .
C13 C 0.93663(6) 0.1991(2) -0.04277(10) 0.0169(3) Uani 1 8 f d . . .
C14 C 0.96330(6) 0.3109(2) 0.04700(10) 0.0155(3) Uani 1 8 f d . . .
C16 C 0.96274(6) 0.8190(2) 0.16764(10) 0.0163(3) Uani 1 8 f d . . .
C17 C 1.0000 0.9271(3) 0.2500 0.0174(4) Uani 1 4 e d S . .
H2 H 0.6871(7) 0.533(3) -0.0428(12) 0.022(4) Uiso 1 8 f d . . .
H11 H 0.8176(7) 0.479(3) -0.1161(12) 0.024(4) Uiso 1 8 f d . . .
H12 H 0.8618(7) 0.185(3) -0.1722(13) 0.030(4) Uiso 1 8 f d . . .
H13 H 0.9548(7) 0.077(3) -0.0625(12) 0.019(4) Uiso 1 8 f d . . .
H14 H 1.0036(7) 0.279(2) 0.0939(13) 0.023(4) Uiso 1 8 f d . . .
H16 H 0.9363(7) 0.894(3) 0.1092(13) 0.026(4) Uiso 1 8 f d . . .
H17 H 1.0000 1.072(4) 0.2500 0.023(6) Uiso 1 4 e d S . .
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
_geom_angle_publ_flag
O15 N10 C11 118.91(11) . . ?
O15 N10 C9 120.86(11) . . ?
C11 N10 C9 120.19(12) . . ?
C8 N18 C8 117.42(17) 2_755 . ?
C2 C1 C3 120.20(12) . 7_655 ?
C2 C1 C6 118.45(12) . . ?
C3 C1 C6 121.34(12) 7_655 . ?
C1 C2 C3 119.81(13) . . ?
C1 C2 H2 120.8(9) . . ?
C3 C2 H2 119.4(9) . . ?
C2 C3 C1 119.99(12) . 7_655 ?
C2 C3 C4 118.58(12) . . ?
C1 C3 C4 121.42(12) 7_655 . ?
N5 C4 C3 178.10(14) . . ?
N7 C6 C1 177.47(15) . . ?
N18 C8 C16 123.07(12) . . ?
N18 C8 C9 114.48(12) . . ?
C16 C8 C9 122.14(12) . . ?
N10 C9 C14 118.83(12) . . ?
N10 C9 C8 119.86(12) . . ?
C14 C9 C8 121.25(12) . . ?
N10 C11 C12 121.43(12) . . ?
N10 C11 H11 114.0(10) . . ?
C12 C11 H11 124.5(10) . . ?
C11 C12 C13 119.65(13) . . ?
C11 C12 H12 119.6(10) . . ?
C13 C12 H12 120.8(10) . . ?
C14 C13 C12 118.54(13) . . ?
C14 C13 H13 122.0(9) . . ?
C12 C13 H13 119.5(9) . . ?
C13 C14 C9 121.25(13) . . ?
C13 C14 H14 122.5(9) . . ?
C9 C14 H14 116.2(9) . . ?
C17 C16 C8 118.48(13) . . ?
C17 C16 H16 119.8(10) . . ?
C8 C16 H16 121.7(10) . . ?
C16 C17 C16 119.16(19) . 2_755 ?
C16 C17 H17 120.42(10) . . ?
C16 C17 H17 120.42(10) 2_755 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O15 N10 1.3069(14) . ?
N5 C4 1.1468(18) . ?
N7 C6 1.1510(18) . ?
N10 C11 1.3658(17) . ?
N10 C9 1.3728(16) . ?
N18 C8 1.3449(15) 2_755 ?
N18 C8 1.3449(15) . ?
C1 C2 1.3931(19) . ?
C1 C3 1.4062(19) 7_655 ?
C1 C6 1.4454(18) . ?
C2 C3 1.3958(18) . ?
C2 H2 0.945(17) . ?
C3 C1 1.4062(19) 7_655 ?
C3 C4 1.4447(19) . ?
C8 C16 1.394(2) . ?
C8 C9 1.4818(18) . ?
C9 C14 1.3908(19) . ?
C11 C12 1.371(2) . ?
C11 H11 0.981(16) . ?
C12 C13 1.3902(19) . ?
C12 H12 1.010(18) . ?
C13 C14 1.3859(19) . ?
C13 H13 0.984(17) . ?
C14 H14 1.010(17) . ?
C16 C17 1.3852(17) . ?
C16 H16 0.977(17) . ?
C17 C16 1.3852(17) 2_755 ?
C17 H17 0.94(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O15 1.080 1.99 3.0380(18) 162 7_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C3 0.2(2) 7_655 . . . ?
C6 C1 C2 C3 178.79(12) . . . . ?
C1 C2 C3 C1 -0.2(2) . . . 7_655 ?
C1 C2 C3 C4 -178.85(12) . . . . ?
C2 C3 C4 N5 44(4) . . . . ?
C1 C3 C4 N5 -135(4) 7_655 . . . ?
C2 C1 C6 N7 -15(4) . . . . ?
C3 C1 C6 N7 164(4) 7_655 . . . ?
C8 N18 C8 C16 -2.68(9) 2_755 . . . ?
C8 N18 C8 C9 171.05(12) 2_755 . . . ?
O15 N10 C9 C14 174.73(12) . . . . ?
C11 N10 C9 C14 -3.04(19) . . . . ?
O15 N10 C9 C8 -8.02(18) . . . . ?
C11 N10 C9 C8 174.21(11) . . . . ?
N18 C8 C9 N10 145.74(11) . . . . ?
C16 C8 C9 N10 -40.46(18) . . . . ?
N18 C8 C9 C14 -37.08(16) . . . . ?
C16 C8 C9 C14 136.72(14) . . . . ?
O15 N10 C11 C12 -174.81(12) . . . . ?
C9 N10 C11 C12 3.0(2) . . . . ?
N10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
C12 C13 C14 C9 2.1(2) . . . . ?
N10 C9 C14 C13 0.5(2) . . . . ?
C8 C9 C14 C13 -176.70(12) . . . . ?
N18 C8 C16 C17 5.26(17) . . . . ?
C9 C8 C16 C17 -168.00(10) . . . . ?
C8 C16 C17 C16 -2.46(8) . . . 2_755 ?
