#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/31/4513106.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_4513106
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, C6 H6 O2'
_chemical_formula_sum            'C16 H14 N4 O2'
_chemical_formula_weight         294.31
_chemical_name_systematic
; 
 (E)-1,2-di(pyridine-4-yl)diazene Resorcinol  
;
_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                94.425(5)
_cell_angle_beta                 106.298(5)
_cell_angle_gamma                113.321(6)
_cell_formula_units_Z            2
_cell_length_a                   8.059(4)
_cell_length_b                   9.776(4)
_cell_length_c                   10.885(4)
_cell_measurement_temperature    293(2)
_cell_volume                     738.4(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7100
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.519
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.519
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0870
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2343
_refine_ls_wR_factor_ref         0.2460
_reflns_number_gt                1768
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00183_si_002.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        738.5(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513106
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 0.8328(3) 0.3430(3) 0.1857(2) 0.0696(7) Uani 1 1 d .
H1A H 0.8026 0.3195 0.1059 0.104 Uiso 1 1 calc R
O2 O 0.1813(3) 0.2805(3) 0.0653(2) 0.0827(8) Uani 1 1 d .
H2B H 0.1837 0.2589 -0.0083 0.124 Uiso 1 1 calc R
N1 N 0.1769(4) 0.1492(3) 0.8259(2) 0.0603(7) Uani 1 1 d .
N2 N 0.2607(4) -0.2520(3) 0.0828(2) 0.0624(8) Uani 1 1 d .
N3 N 0.2686(5) 0.0107(4) 0.4800(3) 0.0836(9) Uani 1 1 d .
N4 N 0.2088(4) -0.1210(3) 0.4486(3) 0.0774(9) Uani 1 1 d .
C1 C 0.2566(5) 0.2419(4) 0.7550(3) 0.0708(10) Uani 1 1 d .
H1B H 0.2965 0.3457 0.7828 0.085 Uiso 1 1 calc R
C2 C 0.2843(5) 0.1956(4) 0.6441(3) 0.0714(9) Uani 1 1 d .
H2A H 0.3411 0.2659 0.5981 0.086 Uiso 1 1 calc R
C3 C 0.2273(5) 0.0449(4) 0.6025(3) 0.0627(9) Uani 1 1 d .
C4 C 0.1426(5) -0.0567(4) 0.6721(3) 0.0664(9) Uani 1 1 d .
H4A H 0.1015 -0.1608 0.6449 0.080 Uiso 1 1 calc R
C5 C 0.1201(5) 0.0007(4) 0.7846(3) 0.0637(9) Uani 1 1 d .
H5 H 0.065(4) -0.063(3) 0.833(3) 0.042(7) Uiso 1 1 d .
C6 C 0.3260(5) -0.1023(4) 0.1318(3) 0.0683(9) Uani 1 1 d .
H6A H 0.3759 -0.0325 0.0832 0.082 Uiso 1 1 calc R
C7 C 0.3216(5) -0.0487(4) 0.2517(3) 0.0680(9) Uani 1 1 d .
H7A H 0.3691 0.0553 0.2839 0.082 Uiso 1 1 calc R
C8 C 0.2455(5) -0.1524(4) 0.3216(3) 0.0601(8) Uani 1 1 d .
C9 C 0.1817(5) -0.3040(4) 0.2739(3) 0.0641(9) Uani 1 1 d .
H9A H 0.1317 -0.3761 0.3207 0.077 Uiso 1 1 calc R
C10 C 0.1932(5) -0.3470(4) 0.1547(3) 0.0647(9) Uani 1 1 d .
H10 H 0.145(5) -0.454(4) 0.119(3) 0.092(11) Uiso 1 1 d .
C11 C 0.6814(4) 0.3473(3) 0.2161(3) 0.0549(8) Uani 1 1 d .
C12 C 0.5078(4) 0.3138(3) 0.1210(3) 0.0553(8) Uani 1 1 d .
H12 H 0.500(5) 0.285(4) 0.030(3) 0.081(10) Uiso 1 1 d .
C13 C 0.3557(5) 0.3167(3) 0.1555(3) 0.0593(8) Uani 1 1 d .
C14 C 0.3801(6) 0.3571(4) 0.2869(3) 0.0664(9) Uani 1 1 d .
H14 H 0.274(5) 0.365(4) 0.304(4) 0.083(10) Uiso 1 1 d .
C15 C 0.5542(6) 0.3909(4) 0.3798(3) 0.0688(10) Uani 1 1 d .
H15 H 0.559(5) 0.403(4) 0.470(3) 0.071(9) Uiso 1 1 d .
C16 C 0.7058(5) 0.3857(4) 0.3473(3) 0.0647(9) Uani 1 1 d .
H16 H 0.825(6) 0.398(5) 0.415(4) 0.104(13) Uiso 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
C1 N1 C5 117.0(3)
C10 N2 C6 117.1(3)
N4 N3 C3 108.0(3)
N3 N4 C8 106.8(3)
N1 C1 C2 124.6(3)
C3 C2 C1 118.4(3)
C2 C3 C4 119.5(3)
C2 C3 N3 112.6(3)
C4 C3 N3 127.9(3)
C3 C4 C5 118.2(3)
N1 C5 C4 122.3(3)
N2 C6 C7 122.4(3)
C8 C7 C6 118.4(3)
C9 C8 C7 119.7(3)
C9 C8 N4 112.8(3)
C7 C8 N4 127.4(3)
C8 C9 C10 118.0(3)
N2 C10 C9 124.4(3)
O1 C11 C12 122.1(3)
O1 C11 C16 117.8(3)
C12 C11 C16 120.1(3)
C11 C12 C13 120.6(3)
O2 C13 C12 122.4(3)
O2 C13 C14 118.0(3)
C12 C13 C14 119.6(3)
C15 C14 C13 118.8(3)
C14 C15 C16 122.3(3)
C15 C16 C11 118.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.367(3)
O2 C13 1.358(4)
N1 C1 1.325(4)
N1 C5 1.333(4)
N2 C10 1.312(4)
N2 C6 1.347(4)
N3 N4 1.164(4)
N3 C3 1.506(5)
N4 C8 1.526(4)
C1 C2 1.363(5)
C2 C3 1.353(5)
C3 C4 1.378(5)
C4 C5 1.395(4)
C6 C7 1.384(4)
C7 C8 1.368(5)
C8 C9 1.363(4)
C9 C10 1.372(4)
C11 C12 1.381(4)
C11 C16 1.386(4)
C12 C13 1.389(4)
C13 C14 1.391(4)
C14 C15 1.374(5)
C15 C16 1.381(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139148024
