#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/31/4513111.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_4513111
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 H6 O3)'
_chemical_formula_sum            'C24 H20 N4 O6'
_chemical_formula_weight         460.44
_chemical_name_systematic
;
 ?
;
_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                 103.444(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6756(14)
_cell_length_b                   6.7322(11)
_cell_length_c                   19.923(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1131.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5379
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                1516
_reflns_number_total             1981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00183_si_006.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4513111
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
N1 N 0.1351(2) 0.0677(3) -0.09078(9) 0.0632(5) Uani 1 1 d .
N2 N 0.0641(2) -0.4576(3) 0.01035(9) 0.0650(5) Uani 1 1 d .
C8 C -0.0049(3) -0.0241(3) -0.10775(12) 0.0701(7) Uani 1 1 d .
H8 H -0.0848 0.0327 -0.1416 0.084 Uiso 1 1 calc R
C9 C -0.0370(3) -0.1986(3) -0.07764(11) 0.0647(6) Uani 1 1 d .
H9 H -0.1356 -0.2594 -0.0911 0.078 Uiso 1 1 calc R
C10 C 0.0821(2) -0.2809(3) -0.02662(10) 0.0555(6) Uani 1 1 d .
C11 C 0.2276(3) -0.1855(3) -0.00884(11) 0.0658(6) Uani 1 1 d .
H11A H 0.3099 -0.2383 0.0249 0.079 Uiso 1 1 calc R
C12 C 0.2482(3) -0.0121(3) -0.04184(11) 0.0664(7) Uani 1 1 d .
H12 H 0.3455 0.0522 -0.0293 0.080 Uiso 1 1 calc R
O1 O 0.4071(2) -0.5758(2) -0.08315(8) 0.0811(6) Uani 1 1 d .
O2 O 0.17086(18) -0.6058(2) -0.15525(8) 0.0736(5) Uani 1 1 d .
H2A H 0.1723 -0.7124 -0.1351 0.110 Uiso 1 1 d R
O3 O 0.57441(19) -0.2628(3) -0.09050(10) 0.0973(7) Uani 1 1 d .
H3A H 0.5424 -0.4052 -0.0785 0.146 Uiso 1 1 d R
C1 C 0.3045(2) -0.5132(3) -0.13188(10) 0.0590(6) Uani 1 1 d .
C2 C 0.3220(2) -0.3260(3) -0.16772(10) 0.0541(5) Uani 1 1 d .
C3 C 0.4571(2) -0.2093(3) -0.14543(12) 0.0647(6) Uani 1 1 d .
C4 C 0.4735(3) -0.0333(4) -0.17895(16) 0.0810(8) Uani 1 1 d .
H4 H 0.5640 0.0438 -0.1640 0.097 Uiso 1 1 calc R
C5 C 0.3577(4) 0.0279(4) -0.23388(15) 0.0875(8) Uani 1 1 d .
H5 H 0.3701 0.1463 -0.2560 0.105 Uiso 1 1 calc R
C6 C 0.2214(4) -0.0846(4) -0.25707(13) 0.0847(8) Uani 1 1 d .
H6 H 0.1428 -0.0426 -0.2945 0.102 Uiso 1 1 calc R
C7 C 0.2051(3) -0.2584(3) -0.22370(11) 0.0671(6) Uani 1 1 d .
H7 H 0.1137 -0.3337 -0.2387 0.081 Uiso 1 1 calc R
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
C12 N1 C8 118.26(19) .
N2 N2 C10 114.3(2) 3_545
N1 C8 C9 123.3(2) .
N1 C8 H8 118.3 .
C9 C8 H8 118.3 .
C8 C9 C10 118.0(2) .
C8 C9 H9 121.0 .
C10 C9 H9 121.0 .
C9 C10 C11 118.8(2) .
C9 C10 N2 124.06(18) .
C11 C10 N2 117.14(18) .
C12 C11 C10 118.9(2) .
C12 C11 H11A 120.5 .
C10 C11 H11A 120.5 .
N1 C12 C11 122.7(2) .
N1 C12 H12 118.6 .
C11 C12 H12 118.6 .
C1 O2 H2A 109.4 .
C3 O3 H3A 103.8 .
O1 C1 O2 122.58(19) .
O1 C1 C2 122.60(18) .
O2 C1 C2 114.81(17) .
C3 C2 C7 118.1(2) .
C3 C2 C1 120.07(19) .
C7 C2 C1 121.83(18) .
O3 C3 C4 118.3(2) .
O3 C3 C2 121.6(2) .
C4 C3 C2 120.1(2) .
C5 C4 C3 120.4(2) .
C5 C4 H4 119.8 .
C3 C4 H4 119.8 .
C4 C5 C6 120.9(2) .
C4 C5 H5 119.6 .
C6 C5 H5 119.6 .
C7 C6 C5 118.7(3) .
C7 C6 H6 120.7 .
C5 C6 H6 120.7 .
C6 C7 C2 121.9(2) .
C6 C7 H7 119.1 .
C2 C7 H7 119.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.325(3) .
N1 C8 1.334(3) .
N2 N2 1.233(3) 3_545
N2 C10 1.427(3) .
C8 C9 1.377(3) .
C8 H8 0.9300 .
C9 C10 1.385(3) .
C9 H9 0.9300 .
C10 C11 1.387(3) .
C11 C12 1.372(3) .
C11 H11A 0.9300 .
C12 H12 0.9300 .
O1 C1 1.229(2) .
O2 C1 1.303(2) .
O2 H2A 0.8201 .
O3 C3 1.358(3) .
O3 H3A 1.0408 .
C1 C2 1.474(3) .
C2 C3 1.395(3) .
C2 C7 1.398(3) .
C3 C4 1.384(3) .
C4 C5 1.366(4) .
C4 H4 0.9300 .
C5 C6 1.389(4) .
C5 H5 0.9300 .
C6 C7 1.370(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
