#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/31/4513103.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_4513103
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 H8 N4, 2(C7 H5 N3 O5)'
_chemical_formula_sum            'C24 H18 N10 O10'
_chemical_formula_weight         606.48
_chemical_name_systematic
; 
 (E)-1,2-di(pyridine-4-yl)diazene 3,5-dinitrobenzamide 
;
_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                106.487(3)
_cell_angle_beta                 98.862(3)
_cell_angle_gamma                95.887(3)
_cell_formula_units_Z            1
_cell_length_a                   6.6042(11)
_cell_length_b                   8.0953(14)
_cell_length_c                   13.127(2)
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.260
_cell_volume                     656.95(19)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            6449
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0433
_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)+(0.0844P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                1625
_reflns_number_total             2374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00183_si_007.cif
_cod_data_source_block           datam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        656.96(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513103
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
O1 O 0.0230(2) 0.1519(2) 0.64140(11) 0.0596(4) Uani 1 1 d .
O2 O -0.7717(3) 0.4793(2) 0.53893(13) 0.0775(5) Uani 1 1 d .
O3 O -0.8445(2) 0.5883(2) 0.69679(13) 0.0743(5) Uani 1 1 d .
O4 O -0.1821(2) 0.3945(2) 0.99923(11) 0.0668(5) Uani 1 1 d .
O5 O -0.3083(2) 0.6348(2) 1.01234(12) 0.0695(5) Uani 1 1 d .
N1 N -0.5723(3) 0.1307(2) 0.32514(14) 0.0591(5) Uani 1 1 d .
N2 N -0.9062(2) -0.0064(2) 0.00495(13) 0.0543(5) Uani 1 1 d .
N3 N -0.2675(3) 0.4956(2) 0.95964(13) 0.0538(5) Uani 1 1 d .
N4 N -0.2273(3) 0.1006(3) 0.49457(14) 0.0596(6) Uani 1 1 d .
H42 H -0.336(4) 0.129(3) 0.4636(17) 0.058(6) Uiso 1 1 d .
H41 H -0.165(4) 0.029(3) 0.4563(19) 0.063(7) Uiso 1 1 d .
N5 N -0.7384(3) 0.5097(2) 0.63686(15) 0.0559(5) Uani 1 1 d .
C1 C -0.7613(4) 0.1737(3) 0.30436(18) 0.0601(6) Uani 1 1 d .
H1 H -0.811(3) 0.234(3) 0.3660(18) 0.074(7) Uiso 1 1 d .
C2 C -0.8799(4) 0.1334(3) 0.20197(17) 0.0553(6) Uani 1 1 d .
H5 H -1.015(4) 0.160(3) 0.1845(17) 0.072(7) Uiso 1 1 d .
C3 C -0.7993(3) 0.0437(3) 0.11547(15) 0.0488(5) Uani 1 1 d .
C4 C -0.6029(3) 0.0010(3) 0.13361(16) 0.0553(6) Uani 1 1 d .
H2A H -0.5436 -0.0563 0.0763 0.066 Uiso 1 1 calc R
C5 C -0.4966(4) 0.0458(3) 0.23926(18) 0.0596(6) Uani 1 1 d .
H3 H -0.359(4) 0.012(3) 0.2521(15) 0.058(6) Uiso 1 1 d .
C6 C -0.3262(3) 0.4462(3) 0.84119(15) 0.0456(5) Uani 1 1 d .
C7 C -0.4991(3) 0.5031(3) 0.79805(17) 0.0471(5) Uani 1 1 d .
H4 H -0.573(3) 0.569(3) 0.8419(16) 0.054(6) Uiso 1 1 d .
C8 C -0.5553(3) 0.4500(2) 0.68722(15) 0.0440(5) Uani 1 1 d .
C9 C -0.4453(3) 0.3464(3) 0.62045(16) 0.0445(5) Uani 1 1 d .
H9 H -0.484(3) 0.319(3) 0.5487(17) 0.049(6) Uiso 1 1 d .
C10 C -0.2718(3) 0.2924(2) 0.66546(14) 0.0418(5) Uani 1 1 d .
C11 C -0.2103(3) 0.3427(3) 0.77789(16) 0.0449(5) Uani 1 1 d .
H8 H -0.101(3) 0.306(2) 0.8113(14) 0.038(5) Uiso 1 1 d .
C12 C -0.1453(3) 0.1759(3) 0.59804(15) 0.0456(5) 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
C1 N1 C5 116.43(19) .
N2 N2 C3 113.6(2) 2_355
O5 N3 O4 124.32(18) .
O5 N3 C6 117.69(19) .
O4 N3 C6 117.98(17) .
O2 N5 O3 124.51(18) .
O2 N5 C8 117.96(16) .
O3 N5 C8 117.52(18) .
N1 C1 C2 124.1(2) .
C3 C2 C1 118.1(2) .
C2 C3 C4 119.37(19) .
C2 C3 N2 123.85(19) .
C4 C3 N2 116.77(18) .
C3 C4 C5 118.2(2) .
N1 C5 C4 123.8(2) .
C7 C6 C11 122.76(19) .
C7 C6 N3 117.81(18) .
C11 C6 N3 119.42(18) .
C8 C7 C6 116.76(18) .
C7 C8 C9 122.76(19) .
C7 C8 N5 118.82(17) .
C9 C8 N5 118.40(17) .
C10 C9 C8 119.43(18) .
C9 C10 C11 119.56(18) .
C9 C10 C12 122.68(17) .
C11 C10 C12 117.74(17) .
C6 C11 C10 118.73(19) .
O1 C12 N4 123.44(18) .
O1 C12 C10 119.48(17) .
N4 C12 C10 117.05(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.228(2) .
O2 N5 1.218(2) .
O3 N5 1.221(2) .
O4 N3 1.226(2) .
O5 N3 1.224(2) .
N1 C1 1.338(3) .
N1 C5 1.341(3) .
N2 N2 1.245(3) 2_355
N2 C3 1.435(2) .
N3 C6 1.469(2) .
N4 C12 1.321(3) .
N5 C8 1.479(3) .
C1 C2 1.379(3) .
C2 C3 1.378(3) .
C3 C4 1.379(3) .
C4 C5 1.382(3) .
C6 C7 1.376(3) .
C6 C11 1.383(3) .
C7 C8 1.373(3) .
C8 C9 1.380(3) .
C9 C10 1.376(3) .
C10 C11 1.396(3) .
C10 C12 1.512(2) .
