#------------------------------------------------------------------------------
#$Date: 2018-08-10 00:30:24 +0300 (Fri, 10 Aug 2018) $
#$Revision: 209521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/05/7110545.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110545
loop_
_publ_author_name
'Zaman, Md. Badruz'
'Tomura, Masaaki'
'Yamashita, Yoshiro'
_publ_section_title
;
 Novel supramolecular synthon in crystal engineering: ionic complexes of
 4,4'-bipyridine and 1,2-bis(2-pyridyl)ethylene with
 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   11
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              999
_journal_page_last               1000
_journal_paper_doi               10.1039/a902305d
_journal_year                    1999
_chemical_formula_moiety         'C12 H12 N2, C6 Cl2 O4'
_chemical_formula_sum            'C18 H12 Cl2 N2 O4'
_chemical_formula_weight         391.21
_chemical_melting_point          215
_chemical_name_systematic
; 
 complex of trans-1,2-bis(2-pyridyl)ethylene and 
 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                91.34(1)
_cell_angle_beta                 99.69(1)
_cell_angle_gamma                111.702(8)
_cell_formula_units_Z            1
_cell_length_a                   9.855(1)
_cell_length_b                   11.245(1)
_cell_length_c                   3.9057(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.5
_cell_volume                     394.67(9)
_computing_cell_refinement       'Rigaku/AFC Diffractometer Control'
_computing_data_collection       'Rigaku/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SHELXS-86
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_av_sigmaI/netI    0.053
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1906
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        1.52
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             200.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.1140
_refine_ls_shift/su_mean         0.0060
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_gt          0.0336
_refine_ls_wR_factor_ref         0.0336
_reflns_number_gt                1258
_reflns_number_total             1804
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            902305dsup1.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_reflns_observed_expression' tag replaced with
'_reflns_threshold_expression' tag as specified in the replacement
file
'cod-tools/trunk/perl-scripts/inputs/replacement_tags.lst'.

'_atom_site_calc_flags'
tag replaced with '_atom_site_calc_flag' tag as specified in the
replacement file
'cod-tools/trunk/perl-scripts/inputs/replacement_tags.lst'.

'_atom_type_scat_imag'
tag replaced with '_atom_type_scat_dispersion_imag' tag as specified
in the replacement file
'cod-tools/trunk/perl-scripts/inputs/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 3137 2015-03-23 15:08:43Z antanas 
;
_cod_original_cell_volume        394.68(10)
_cod_original_formula_sum        'C18 H12 Cl2 N2 O4 '
_cod_database_code               7110545
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_calc_flag
Cl(1) Cl 0.22789(7) 0.27042(6) 0.3776(2) 0.0370(2) Uani 1.00 d
O(1) O -0.0600(2) 0.2130(2) -0.1045(5) 0.0355(5) Uani 1.00 d
O(2) O 0.2515(2) 0.0115(2) 0.4220(5) 0.0420(5) Uani 1.00 d
N(1) N 0.2538(2) 0.7558(2) 0.6184(5) 0.0284(5) Uani 1.00 d
C(1) C 0.3945(3) 0.8295(2) 0.7628(7) 0.0342(6) Uani 1.00 d
C(2) C 0.4827(3) 0.7798(3) 0.9733(7) 0.0368(7) Uani 1.00 d
C(3) C 0.4216(3) 0.6508(3) 1.0304(7) 0.0379(7) Uani 1.00 d
C(4) C 0.2767(3) 0.5760(2) 0.8822(7) 0.0323(6) Uani 1.00 d
C(5) C 0.1906(2) 0.6306(2) 0.6731(6) 0.0268(6) Uani 1.00 d
C(6) C 0.0349(3) 0.5626(2) 0.5072(7) 0.0312(6) Uani 1.00 d
C(7) C -0.0260(3) 0.1176(2) -0.0456(6) 0.0268(6) Uani 1.00 d
C(8) C 0.1024(2) 0.1214(2) 0.1727(6) 0.0275(6) Uani 1.00 d
C(9) C 0.1382(3) 0.0130(2) 0.2319(6) 0.0273(6) Uani 1.00 d
H(1) H 0.433(3) 0.924(3) 0.703(8) 0.054(9) Uiso 1.00 d
H(2) H 0.583(3) 0.831(3) 1.078(7) 0.040(7) Uiso 1.00 d
H(3) H 0.483(3) 0.614(3) 1.170(7) 0.041(8) Uiso 1.00 d
H(4) H 0.235(3) 0.491(3) 0.922(7) 0.032(7) Uiso 1.00 d
H(5) H -0.018(3) 0.615(3) 0.412(7) 0.041(7) Uiso 1.00 d
H(6) H 0.197(4) 0.792(3) 0.453(9) 0.066(10) Uiso 1.00 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl(1) 0.0339(3) 0.0275(3) 0.0407(4) 0.0071(2) -0.0049(2) -0.0040(2)
O(1) 0.0372(10) 0.0278(9) 0.040(1) 0.0149(7) -0.0037(8) 0.0013(7)
O(2) 0.0333(10) 0.0376(10) 0.048(1) 0.0145(8) -0.0118(8) 0.0004(8)
N(1) 0.027(1) 0.0257(10) 0.031(1) 0.0100(8) 0.0012(8) 0.0029(8)
C(1) 0.029(1) 0.031(1) 0.036(1) 0.0056(10) 0.003(1) -0.001(1)
C(2) 0.025(1) 0.040(1) 0.036(1) 0.007(1) -0.003(1) -0.006(1)
C(3) 0.034(1) 0.045(1) 0.034(1) 0.018(1) -0.005(1) 0.000(1)
C(4) 0.034(1) 0.027(1) 0.033(1) 0.011(1) 0.000(1) 0.0038(10)
C(5) 0.026(1) 0.025(1) 0.028(1) 0.0088(9) 0.0044(9) 0.0006(9)
C(6) 0.026(1) 0.028(1) 0.037(1) 0.0101(9) -0.0015(10) 0.004(1)
C(7) 0.027(1) 0.025(1) 0.026(1) 0.0092(9) 0.0029(9) 0.0042(9)
C(8) 0.026(1) 0.024(1) 0.028(1) 0.0055(9) 0.0013(9) 0.0003(9)
C(9) 0.025(1) 0.029(1) 0.027(1) 0.0100(9) 0.0014(9) 0.0037(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 4 1
-4 4 0
-2 3 0
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) N(1) C(5) 122.5(2) 1_555 1_555 1_555 yes
C(1) N(1) H(6) 118(1) 1_555 1_555 1_555 yes
C(5) N(1) H(6) 118(1) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 120.9(2) 1_555 1_555 1_555 yes
N(1) C(1) H(1) 116(1) 1_555 1_555 1_555 yes
C(2) C(1) H(1) 122(1) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 117.9(2) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 121(1) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 120(1) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.8(2) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 118(1) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120(1) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.4(2) 1_555 1_555 1_555 yes
C(3) C(4) H(4) 121(1) 1_555 1_555 1_555 yes
C(5) C(4) H(4) 119(1) 1_555 1_555 1_555 yes
N(1) C(5) C(4) 118.5(2) 1_555 1_555 1_555 yes
N(1) C(5) C(6) 116.8(2) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 124.8(2) 1_555 1_555 1_555 yes
C(5) C(6) C(6) 123.7(3) 1_555 1_555 2_566 yes
C(5) C(6) H(5) 116(1) 1_555 1_555 1_555 yes
C(6) C(6) H(5) 119(1) 2_566 1_555 1_555 yes
O(1) C(7) C(8) 125.0(2) 1_555 1_555 1_555 yes
O(1) C(7) C(9) 116.2(2) 1_555 1_555 2_555 yes
C(8) C(7) C(9) 118.8(2) 1_555 1_555 2_555 yes
Cl(1) C(8) C(7) 117.9(2) 1_555 1_555 1_555 yes
Cl(1) C(8) C(9) 118.4(2) 1_555 1_555 1_555 yes
C(7) C(8) C(9) 123.7(2) 1_555 1_555 1_555 yes
O(2) C(9) C(7) 116.4(2) 1_555 1_555 2_555 yes
O(2) C(9) C(8) 126.1(2) 1_555 1_555 1_555 yes
C(7) C(9) C(8) 117.5(2) 2_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl(1) C(8) 1.746(2) 1_555 1_555 yes
O(1) C(7) 1.252(3) 1_555 1_555 yes
O(2) C(9) 1.238(3) 1_555 1_555 yes
N(1) C(1) 1.339(3) 1_555 1_555 yes
N(1) C(5) 1.351(3) 1_555 1_555 yes
N(1) H(6) 0.98(3) 1_555 1_555 yes
C(1) C(2) 1.372(4) 1_555 1_555 yes
C(1) H(1) 1.03(3) 1_555 1_555 yes
C(2) C(3) 1.389(4) 1_555 1_555 yes
C(2) H(2) 0.95(3) 1_555 1_555 yes
C(3) C(4) 1.376(3) 1_555 1_555 yes
C(3) H(3) 0.96(3) 1_555 1_555 yes
C(4) C(5) 1.393(3) 1_555 1_555 yes
C(4) H(4) 0.92(3) 1_555 1_555 yes
C(5) C(6) 1.461(3) 1_555 1_555 yes
C(6) C(6) 1.313(5) 1_555 2_566 yes
C(6) H(5) 0.96(3) 1_555 1_555 yes
C(7) C(8) 1.387(3) 1_555 1_555 yes
C(7) C(9) 1.545(3) 1_555 2_555 yes
C(8) C(9) 1.403(3) 1_555 1_555 yes
