#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510197.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_4510197
loop_
_publ_author_name
'Zhou, Jie'
'Du, Lin'
'Qiao, Yong-Feng'
'Hu, Yan'
'Li, Bin'
'Li, Lin'
'Wang, Xiao-Yuan'
'Yang, Jing'
'Xie, Ming-Jin'
'Zhao, Qi-Hua'
_publ_section_title
;
 Intriguing Architectures Generated from 1,4-Bis(3- or
 4-pyridyl)-2,3-diaza-1,3-butadiene with Aromatic Dicarboxylates:
 Syntheses, Crystal Structures, and Properties
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1175
_journal_paper_doi               10.1021/cg401692e
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C20 H14 N4 O4 Zn'
_chemical_formula_sum            'C20 H14 N4 O4 Zn'
_chemical_formula_weight         439.72
_chemical_name_systematic
; 
 ? 
;
_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                112.995(2)
_cell_angle_beta                 99.133(3)
_cell_angle_gamma                99.881(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2609(16)
_cell_length_b                   10.149(2)
_cell_length_c                   12.461(2)
_cell_measurement_reflns_used    881
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.21
_cell_volume                     917.6(3)
_computing_cell_refinement       'Bruker apex II'
_computing_data_collection       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0808
_diffrn_reflns_av_sigmaI/netI    0.1326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7060
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  0.8524
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+1.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1821
_reflns_number_total             3256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401692e_si_001.cif
_cod_data_source_block           1
_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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4510197
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
N1 N 0.2333(6) 0.5382(5) 0.8770(4) 0.0337(13) Uani 1 1 d .
N2 N 0.3649(8) 0.6672(7) 0.6155(5) 0.072(2) Uani 1 1 d .
N3 N 0.4025(8) 0.6867(7) 0.5152(5) 0.068(2) Uani 1 1 d .
N4 N 0.5416(6) 0.7841(5) 0.2437(4) 0.0374(13) Uani 1 1 d .
O1 O 0.2837(5) 0.4998(4) 1.1085(3) 0.0361(11) Uani 1 1 d .
O2 O 0.3979(5) 0.3322(4) 0.9919(4) 0.0404(11) Uani 1 1 d .
O3 O 0.1885(5) -0.2027(5) 1.1351(4) 0.0594(14) Uani 1 1 d .
O4 O 0.3723(6) -0.1371(5) 1.0449(4) 0.0502(13) Uani 1 1 d .
Zn1 Zn 0.37853(10) 0.66329(8) 1.06107(6) 0.0323(2) Uani 1 1 d .
C1 C 0.2803(7) 0.5777(7) 0.7940(5) 0.0385(17) Uani 1 1 d .
H1 H 0.3690 0.6615 0.8186 0.046 Uiso 1 1 calc R
C2 C 0.2008(8) 0.4976(7) 0.6712(5) 0.0462(19) Uani 1 1 d .
C3 C 0.0674(9) 0.3744(7) 0.6357(6) 0.055(2) Uani 1 1 d .
H3 H 0.0134 0.3180 0.5546 0.066 Uiso 1 1 calc R
C4 C 0.0153(8) 0.3362(7) 0.7217(6) 0.052(2) Uani 1 1 d .
H4 H -0.0760 0.2553 0.7000 0.063 Uiso 1 1 calc R
C5 C 0.1023(7) 0.4211(7) 0.8417(5) 0.0401(17) Uani 1 1 d .
H5 H 0.0676 0.3950 0.8997 0.048 Uiso 1 1 calc R
C6 C 0.2597(9) 0.5438(8) 0.5818(6) 0.055(2) Uani 1 1 d .
H6 H 0.2187 0.4814 0.5001 0.066 Uiso 1 1 calc R
C7 C 0.5292(9) 0.7926(8) 0.5448(6) 0.060(2) Uani 1 1 d .
H7 H 0.5863 0.8472 0.6255 0.072 Uiso 1 1 calc R
C8 C 0.5892(8) 0.8319(8) 0.4528(5) 0.0453(18) Uani 1 1 d .
C9 C 0.4994(8) 0.7530(7) 0.3313(5) 0.0402(17) Uani 1 1 d .
H9 H 0.4055 0.6749 0.3112 0.048 Uiso 1 1 calc R
C10 C 0.6735(8) 0.8970(7) 0.2732(6) 0.0494(19) Uani 1 1 d .
H10 H 0.7028 0.9209 0.2128 0.059 Uiso 1 1 calc R
C11 C 0.7702(9) 0.9817(8) 0.3910(6) 0.063(2) Uani 1 1 d .
H11 H 0.8632 1.0593 0.4084 0.075 Uiso 1 1 calc R
C12 C 0.7262(9) 0.9489(8) 0.4814(6) 0.062(2) Uani 1 1 d .
H12 H 0.7881 1.0051 0.5609 0.075 Uiso 1 1 calc R
C13 C 0.3120(8) 0.3730(7) 1.0667(5) 0.0315(16) Uani 1 1 d .
C14 C 0.2288(7) 0.2629(6) 1.1088(5) 0.0264(14) Uani 1 1 d .
C15 C 0.2759(7) 0.1298(6) 1.0836(5) 0.0294(15) Uani 1 1 d .
H15 H 0.3582 0.1095 1.0410 0.035 Uiso 1 1 calc R
C16 C 0.2013(7) 0.0275(6) 1.1216(5) 0.0279(14) Uani 1 1 d .
C17 C 0.0766(8) 0.0579(7) 1.1818(5) 0.0427(18) Uani 1 1 d .
H17 H 0.0229 -0.0119 1.2045 0.051 Uiso 1 1 calc R
C18 C 0.0282(8) 0.1907(7) 1.2100(6) 0.050(2) Uani 1 1 d .
H18 H -0.0556 0.2096 1.2515 0.060 Uiso 1 1 calc R
C19 C 0.1087(8) 0.2947(7) 1.1745(5) 0.0395(17) Uani 1 1 d .
H19 H 0.0813 0.3851 1.1951 0.047 Uiso 1 1 calc R
C20 C 0.2567(8) -0.1127(6) 1.0991(6) 0.0330(16) 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'
Zn Zn 0.2839 1.4301 '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
C5 N1 C1 118.5(5) . .
C5 N1 Zn1 123.3(4) . .
C1 N1 Zn1 118.2(4) . .
C6 N2 N3 110.6(5) . .
C7 N3 N2 112.3(5) . .
C10 N4 C9 118.0(5) . .
C10 N4 Zn1 122.4(4) . 1_554
C9 N4 Zn1 119.4(4) . 1_554
C13 O1 Zn1 123.1(4) . .
C13 O2 Zn1 153.3(4) . 2_667
C20 O3 Zn1 85.5(4) . 1_545
C20 O4 Zn1 94.5(4) . 1_545
O1 Zn1 O2 119.54(17) . 2_667
O1 Zn1 O4 151.19(18) . 1_565
O2 Zn1 O4 89.11(17) 2_667 1_565
O1 Zn1 N1 92.45(16) . .
O2 Zn1 N1 91.12(17) 2_667 .
O4 Zn1 N1 89.78(16) 1_565 .
O1 Zn1 N4 88.06(16) . 1_556
O2 Zn1 N4 84.99(17) 2_667 1_556
O4 Zn1 N4 91.78(17) 1_565 1_556
N1 Zn1 N4 175.8(2) . 1_556
O1 Zn1 O3 92.42(16) . 1_565
O2 Zn1 O3 146.24(15) 2_667 1_565
O4 Zn1 O3 58.87(16) 1_565 1_565
N1 Zn1 O3 98.53(17) . 1_565
N4 Zn1 O3 85.62(18) 1_556 1_565
O1 Zn1 C20 121.81(19) . 1_565
O2 Zn1 C20 117.83(19) 2_667 1_565
O4 Zn1 C20 29.49(15) 1_565 1_565
N1 Zn1 C20 95.44(18) . 1_565
N4 Zn1 C20 87.83(18) 1_556 1_565
O3 Zn1 C20 29.39(16) 1_565 1_565
N1 C1 C2 122.4(6) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 118.4(6) . .
C3 C2 C6 121.1(6) . .
C1 C2 C6 120.5(6) . .
C4 C3 C2 119.3(6) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C3 C4 C5 118.5(6) . .
C3 C4 H4 120.7 . .
C5 C4 H4 120.7 . .
N1 C5 C4 122.8(6) . .
N1 C5 H5 118.6 . .
C4 C5 H5 118.6 . .
N2 C6 C2 120.7(6) . .
N2 C6 H6 119.7 . .
C2 C6 H6 119.7 . .
N3 C7 C8 120.8(6) . .
N3 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C12 C8 C9 117.6(6) . .
C12 C8 C7 122.7(6) . .
C9 C8 C7 119.7(6) . .
N4 C9 C8 123.5(6) . .
N4 C9 H9 118.3 . .
C8 C9 H9 118.3 . .
N4 C10 C11 122.7(6) . .
N4 C10 H10 118.6 . .
C11 C10 H10 118.6 . .
C12 C11 C10 119.1(6) . .
C12 C11 H11 120.5 . .
C10 C11 H11 120.5 . .
C11 C12 C8 119.2(6) . .
C11 C12 H12 120.4 . .
C8 C12 H12 120.4 . .
O2 C13 O1 124.7(5) . .
O2 C13 C14 118.8(6) . .
O1 C13 C14 116.5(6) . .
C19 C14 C15 119.6(5) . .
C19 C14 C13 120.4(5) . .
C15 C14 C13 120.1(5) . .
C16 C15 C14 121.0(6) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C17 C16 C15 118.6(6) . .
C17 C16 C20 120.3(5) . .
C15 C16 C20 121.1(6) . .
C16 C17 C18 121.9(6) . .
C16 C17 H17 119.0 . .
C18 C17 H17 119.0 . .
C17 C18 C19 118.7(6) . .
C17 C18 H18 120.7 . .
C19 C18 H18 120.7 . .
C14 C19 C18 120.2(6) . .
C14 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
O3 C20 O4 121.0(6) . .
O3 C20 C16 119.9(6) . .
O4 C20 C16 119.0(5) . .
O3 C20 Zn1 65.1(3) . 1_545
O4 C20 Zn1 56.0(3) . 1_545
C16 C20 Zn1 174.4(4) . 1_545
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.333(7) .
N1 C1 1.334(6) .
N1 Zn1 2.154(4) .
N2 C6 1.265(8) .
N2 N3 1.411(6) .
N3 C7 1.253(8) .
N4 C10 1.323(7) .
N4 C9 1.329(6) .
N4 Zn1 2.186(5) 1_554
O1 C13 1.265(7) .
O1 Zn1 2.045(3) .
O2 C13 1.247(7) .
O2 Zn1 2.056(4) 2_667
O3 C20 1.255(6) .
O3 Zn1 2.319(5) 1_545
O4 C20 1.259(7) .
O4 Zn1 2.121(4) 1_545
Zn1 O2 2.056(4) 2_667
Zn1 O4 2.121(4) 1_565
Zn1 N4 2.186(5) 1_556
Zn1 O3 2.319(5) 1_565
Zn1 C20 2.550(6) 1_565
C1 C2 1.399(8) .
C1 H1 0.9300 .
C2 C3 1.383(8) .
C2 C6 1.483(8) .
C3 C4 1.378(8) .
C3 H3 0.9300 .
C4 C5 1.391(8) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.479(8) .
C7 H7 0.9300 .
C8 C12 1.377(8) .
C8 C9 1.406(7) .
C9 H9 0.9300 .
C10 C11 1.392(8) .
C10 H10 0.9300 .
C11 C12 1.376(8) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.518(7) .
C14 C19 1.386(7) .
C14 C15 1.401(7) .
C15 C16 1.392(7) .
C15 H15 0.9300 .
C16 C17 1.376(8) .
C16 C20 1.506(8) .
C17 C18 1.400(8) .
C17 H17 0.9300 .
C18 C19 1.403(7) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 Zn1 2.550(6) 1_545
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 N2 N3 C7 -167.0(8) . .
C13 O1 Zn1 O2 -27.9(5) . 2_667
C13 O1 Zn1 O4 158.8(4) . 1_565
C13 O1 Zn1 N1 64.8(4) . .
C13 O1 Zn1 N4 -111.0(4) . 1_556
C13 O1 Zn1 O3 163.5(4) . 1_565
C13 O1 Zn1 C20 162.8(4) . 1_565
C5 N1 Zn1 O1 15.7(5) . .
C1 N1 Zn1 O1 -162.3(4) . .
C5 N1 Zn1 O2 135.4(5) . 2_667
C1 N1 Zn1 O2 -42.7(4) . 2_667
C5 N1 Zn1 O4 -135.5(5) . 1_565
C1 N1 Zn1 O4 46.5(4) . 1_565
C5 N1 Zn1 N4 113(3) . 1_556
C1 N1 Zn1 N4 -65(3) . 1_556
C5 N1 Zn1 O3 -77.1(5) . 1_565
C1 N1 Zn1 O3 104.9(4) . 1_565
C5 N1 Zn1 C20 -106.6(5) . 1_565
C1 N1 Zn1 C20 75.4(4) . 1_565
C5 N1 C1 C2 -2.3(9) . .
Zn1 N1 C1 C2 175.8(5) . .
N1 C1 C2 C3 0.9(10) . .
N1 C1 C2 C6 -178.7(6) . .
C1 C2 C3 C4 1.1(10) . .
C6 C2 C3 C4 -179.3(6) . .
C2 C3 C4 C5 -1.7(10) . .
C1 N1 C5 C4 1.7(9) . .
Zn1 N1 C5 C4 -176.3(5) . .
C3 C4 C5 N1 0.3(10) . .
N3 N2 C6 C2 179.8(6) . .
C3 C2 C6 N2 170.0(7) . .
C1 C2 C6 N2 -10.4(11) . .
N2 N3 C7 C8 -179.8(6) . .
N3 C7 C8 C12 178.9(7) . .
N3 C7 C8 C9 2.4(11) . .
C10 N4 C9 C8 -1.2(9) . .
Zn1 N4 C9 C8 -175.2(5) 1_554 .
C12 C8 C9 N4 1.1(10) . .
C7 C8 C9 N4 177.8(6) . .
C9 N4 C10 C11 1.2(10) . .
Zn1 N4 C10 C11 175.0(5) 1_554 .
N4 C10 C11 C12 -1.1(11) . .
C10 C11 C12 C8 1.0(11) . .
C9 C8 C12 C11 -1.0(11) . .
C7 C8 C12 C11 -177.6(7) . .
Zn1 O2 C13 O1 68.9(11) 2_667 .
Zn1 O2 C13 C14 -113.4(8) 2_667 .
Zn1 O1 C13 O2 -0.9(8) . .
Zn1 O1 C13 C14 -178.6(3) . .
O2 C13 C14 C19 -168.4(5) . .
O1 C13 C14 C19 9.4(8) . .
O2 C13 C14 C15 13.0(7) . .
O1 C13 C14 C15 -169.1(5) . .
C19 C14 C15 C16 1.3(8) . .
C13 C14 C15 C16 179.9(5) . .
C14 C15 C16 C17 1.7(8) . .
C14 C15 C16 C20 -177.5(5) . .
C15 C16 C17 C18 -2.7(8) . .
C20 C16 C17 C18 176.5(5) . .
C16 C17 C18 C19 0.6(9) . .
C15 C14 C19 C18 -3.4(8) . .
C13 C14 C19 C18 178.0(5) . .
C17 C18 C19 C14 2.5(9) . .
Zn1 O3 C20 O4 2.3(5) 1_545 .
Zn1 O3 C20 C16 -177.1(5) 1_545 .
Zn1 O4 C20 O3 -2.5(6) 1_545 .
Zn1 O4 C20 C16 176.9(4) 1_545 .
C17 C16 C20 O3 0.2(8) . .
C15 C16 C20 O3 179.4(5) . .
C17 C16 C20 O4 -179.3(5) . .
C15 C16 C20 O4 -0.1(8) . .
C17 C16 C20 Zn1 -152(4) . 1_545
C15 C16 C20 Zn1 27(4) . 1_545
