#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/31/4513104.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_4513104
loop_
_publ_author_name
'Ravat, Prince'
'SeethaLekshmi, Sunil'
'Biswas, Sharmita Nandy'
'Nandy, Purnendu'
'Varughese, Sunil'
_publ_section_title
;
 Equivalence of Ethylene and Azo-Bridges in the Modular Design of
 Molecular Complexes: Role of Weak Interactions
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2389
_journal_paper_doi               10.1021/acs.cgd.5b00183
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C10 H10 N4, C10 H4 O8'
_chemical_formula_sum            'C20 H14 N4 O8'
_chemical_formula_weight         438.35
_chemical_name_systematic
; 
 (E)-1,2-di(pyridin-4-yl)diazene 1,2,4,5-benzenetetracarboxylic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 109.464(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.749(4)
_cell_length_b                   7.643(3)
_cell_length_c                   13.372(5)
_cell_measurement_temperature    100
_cell_volume                     939.4(6)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD-Area detector'
_diffrn_measurement_method       SMART
_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  0.0854
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6412
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0669
_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)+(0.0871P)²+0.9981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                1500
_reflns_number_total             1659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00183_si_005.cif
_cod_data_source_block           data
_cod_original_cell_volume        939.5(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4513104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_calc_flag
_atom_site_refinement_flags
O1 O 1.2876(2) -0.0335(3) 1.26108(14) 0.0312(5) Uani 1 1 d .
O2 O 1.1548(2) -0.2776(3) 1.22773(15) 0.0332(5) Uani 1 1 d .
H200 H 1.2010 -0.2990 1.2900 0.029(8) Uiso 1 1 calc R
O3 O 0.69052(18) 0.1331(3) 1.08043(14) 0.0279(5) Uani 1 1 d .
O4 O 0.6425(2) 0.2188(3) 0.91314(15) 0.0366(6) Uani 1 1 d .
N1 N 1.4414(2) -0.7253(3) 1.06789(19) 0.0271(6) Uani 1 1 d .
H11 H 1.533(5) -0.775(5) 1.075(3) 0.072(13) Uiso 1 1 d .
N2 N 1.0296(2) -0.5456(3) 1.03998(18) 0.0249(5) Uani 1 1 d .
C1 C 1.4013(3) -0.7137(4) 1.1534(2) 0.0292(6) Uani 1 1 d .
H1 H 1.463(4) -0.750(4) 1.214(3) 0.035(9) Uiso 1 1 d .
C2 C 1.2650(3) -0.6522(4) 1.1447(2) 0.0280(6) Uani 1 1 d .
H2A H 1.2358 -0.6444 1.2040 0.034 Uiso 1 1 calc R
C3 C 1.1729(3) -0.6024(3) 1.0460(2) 0.0231(6) Uani 1 1 d .
C4 C 1.2166(3) -0.6141(4) 0.9579(2) 0.0283(6) Uani 1 1 d .
H4 H 1.151(3) -0.577(4) 0.888(3) 0.033(8) Uiso 1 1 d .
C5 C 1.3540(3) -0.6770(4) 0.9717(2) 0.0283(6) Uani 1 1 d .
H5 H 1.388(4) -0.690(4) 0.917(3) 0.033(8) Uiso 1 1 d .
C6 C 1.0967(3) -0.0643(3) 1.0950(2) 0.0199(6) Uani 1 1 d .
C7 C 0.9620(3) 0.0045(3) 1.0902(2) 0.0202(6) Uani 1 1 d .
H7 H 0.941(3) 0.007(3) 1.150(2) 0.011(6) Uiso 1 1 d .
C8 C 0.8647(3) 0.0699(3) 0.9963(2) 0.0201(6) Uani 1 1 d .
C9 C 1.1938(3) -0.1240(3) 1.20223(19) 0.0205(6) Uani 1 1 d .
C10 C 0.7208(3) 0.1481(3) 0.99463(19) 0.0209(6) 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 0.0016 '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
C1 N1 C5 122.3(2) . .
N2 N2 C3 112.3(3) 3_747 .
N1 C1 C2 120.1(3) . .
C1 C2 C3 118.5(3) . .
C2 C3 C4 120.7(2) . .
C2 C3 N2 116.6(2) . .
C4 C3 N2 122.7(2) . .
C5 C4 C3 118.1(3) . .
N1 C5 C4 120.3(3) . .
C8 C6 C7 119.7(2) 3_757 .
C8 C6 C9 124.0(2) 3_757 .
C7 C6 C9 116.3(2) . .
C8 C7 C6 121.7(2) . .
C7 C8 C6 118.6(2) . 3_757
C7 C8 C10 120.3(2) . .
C6 C8 C10 121.1(2) 3_757 .
O1 C9 O2 124.4(2) . .
O1 C9 C6 123.3(2) . .
O2 C9 C6 112.0(2) . .
O4 C10 O3 125.0(2) . .
O4 C10 C8 119.0(2) . .
O3 C10 C8 116.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.206(3) .
O2 C9 1.314(3) .
O3 C10 1.281(3) .
O4 C10 1.228(3) .
N1 C1 1.329(4) .
N1 C5 1.337(4) .
N2 N2 1.246(4) 3_747
N2 C3 1.440(3) .
C1 C2 1.377(4) .
C2 C3 1.379(4) .
C3 C4 1.382(4) .
C4 C5 1.377(4) .
C6 C8 1.394(4) 3_757
C6 C7 1.396(3) .
C6 C9 1.502(3) .
C7 C8 1.389(4) .
C8 C6 1.394(4) 3_757
C8 C10 1.519(3) .
