#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:02:21 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179649 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/02/4510202.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_4510202
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         '2(C18 H11 N2 O4 Zn), H2O'
_chemical_formula_sum            'C36 H24 N4 O9 Zn2'
_chemical_formula_weight         787.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.3200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2139(15)
_cell_length_b                   11.7900(10)
_cell_length_c                   16.5932(13)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.30
_cell_volume                     3319.4(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12756
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0278
_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)+(0.0332P)²+5.0699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2520
_reflns_number_total             2963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401692e_si_001.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               4510202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.41651(12) 0.69457(18) 0.02259(13) 0.0302(5) Uani 1 1 d .
N2 N 0.46993(16) 0.7563(3) -0.23329(16) 0.0637(8) Uani 1 1 d .
O1 O 0.55314(10) 0.55785(17) 0.17122(13) 0.0430(5) Uani 1 1 d .
O2 O 0.60483(11) 0.55903(18) 0.31569(13) 0.0489(5) Uani 1 1 d .
O3 O 0.94689(11) 0.29358(17) 0.33129(12) 0.0438(5) Uani 1 1 d .
O4 O 0.90257(11) 0.29027(18) 0.18770(12) 0.0457(5) Uani 1 1 d .
O5 O 0.5000 1.0000 0.0000 0.545(14) Uani 1 2 d S
H5A H 0.4893 0.9611 -0.0460 0.654 Uiso 0.50 1 d PR
H5B H 0.5149 0.9670 0.0489 0.654 Uiso 0.50 1 d PR
Zn1 Zn 0.466252(15) 0.67146(2) 0.153356(16) 0.02421(10) Uani 1 1 d .
C1 C 0.45965(16) 0.6868(3) -0.02728(17) 0.0417(7) Uani 1 1 d .
H1 H 0.5087 0.6520 -0.0045 0.050 Uiso 1 1 calc R
C2 C 0.43518(16) 0.7279(3) -0.11085(16) 0.0412(7) Uani 1 1 d .
C3 C 0.36125(18) 0.7761(3) -0.14512(17) 0.0457(7) Uani 1 1 d .
H3 H 0.3426 0.8042 -0.2013 0.055 Uiso 1 1 calc R
C4 C 0.31563(18) 0.7819(3) -0.09548(18) 0.0541(9) Uani 1 1 d .
H4 H 0.2652 0.8128 -0.1177 0.065 Uiso 1 1 calc R
C5 C 0.34565(16) 0.7413(3) -0.01192(17) 0.0446(7) Uani 1 1 d .
H5 H 0.3148 0.7470 0.0219 0.054 Uiso 1 1 calc R
C6 C 0.48906(19) 0.7227(3) -0.15787(19) 0.0599(9) Uani 1 1 d .
H6 H 0.5394 0.6933 -0.1302 0.072 Uiso 1 1 calc R
C7 C 0.60813(15) 0.5401(2) 0.24274(18) 0.0349(6) Uani 1 1 d .
C8 C 0.68541(14) 0.4928(2) 0.24289(16) 0.0317(6) Uani 1 1 d .
C9 C 0.72745(16) 0.4261(2) 0.31136(17) 0.0408(7) Uani 1 1 d .
H9 H 0.7081 0.4132 0.3553 0.049 Uiso 1 1 calc R
C10 C 0.79878(16) 0.3768(3) 0.31695(17) 0.0411(7) Uani 1 1 d .
H10 H 0.8258 0.3313 0.3643 0.049 Uiso 1 1 calc R
C11 C 0.82969(14) 0.3941(2) 0.25416(16) 0.0320(6) Uani 1 1 d .
C12 C 0.79058(14) 0.4687(2) 0.18383(16) 0.0310(6) Uani 1 1 d .
C13 C 0.82404(16) 0.4995(2) 0.12173(18) 0.0421(7) Uani 1 1 d .
H13 H 0.8730 0.4705 0.1267 0.050 Uiso 1 1 calc R
C14 C 0.78567(19) 0.5707(3) 0.0551(2) 0.0566(9) Uani 1 1 d .
H14 H 0.8082 0.5892 0.0147 0.068 Uiso 1 1 calc R
C15 C 0.7129(2) 0.6157(3) 0.0472(2) 0.0601(9) Uani 1 1 d .
H15 H 0.6866 0.6633 0.0010 0.072 Uiso 1 1 calc R
C16 C 0.67956(17) 0.5911(3) 0.10648(18) 0.0453(7) Uani 1 1 d .
H16 H 0.6312 0.6232 0.1005 0.054 Uiso 1 1 calc R
C17 C 0.71698(15) 0.5174(2) 0.17705(16) 0.0317(6) Uani 1 1 d .
C18 C 0.89938(15) 0.3225(2) 0.25806(17) 0.0334(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'
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 117.4(2) . .
C5 N1 Zn1 120.01(17) . .
C1 N1 Zn1 121.02(17) . .
C6 N2 N2 115.4(3) . 2_654
C7 O1 Zn1 124.22(17) . .
C7 O2 Zn1 127.96(18) . 2_655
C18 O3 Zn1 122.06(17) . 4_645
C18 O4 Zn1 134.29(18) . 3_545
H5A O5 H5B 120.0 . .
O1 Zn1 O4 156.68(8) . 3_455
O1 Zn1 N1 105.47(8) . .
O4 Zn1 N1 97.37(8) 3_455 .
O1 Zn1 O2 93.86(9) . 2_655
O4 Zn1 O2 84.15(9) 3_455 2_655
N1 Zn1 O2 106.05(8) . 2_655
O1 Zn1 O3 85.44(8) . 4_655
O4 Zn1 O3 88.56(9) 3_455 4_655
N1 Zn1 O3 93.52(8) . 4_655
O2 Zn1 O3 159.81(8) 2_655 4_655
O1 Zn1 Zn1 81.21(6) . 2_655
O4 Zn1 Zn1 75.68(5) 3_455 2_655
N1 Zn1 Zn1 172.05(6) . 2_655
O2 Zn1 Zn1 77.37(6) 2_655 2_655
O3 Zn1 Zn1 82.59(5) 4_655 2_655
N1 C1 C2 123.4(3) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C3 C2 C1 117.9(2) . .
C3 C2 C6 122.8(3) . .
C1 C2 C6 119.2(3) . .
C4 C3 C2 119.2(3) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 118.8(3) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
N1 C5 C4 123.1(2) . .
N1 C5 H5 118.4 . .
C4 C5 H5 118.4 . .
N2 C6 C2 122.1(3) . .
N2 C6 H6 119.0 . .
C2 C6 H6 119.0 . .
O2 C7 O1 125.3(2) . .
O2 C7 C8 115.8(2) . .
O1 C7 C8 118.9(2) . .
C9 C8 C17 119.4(2) . .
C9 C8 C7 117.0(2) . .
C17 C8 C7 123.6(2) . .
C8 C9 C10 121.5(2) . .
C8 C9 H9 119.3 . .
C10 C9 H9 119.3 . .
C11 C10 C9 121.2(2) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C10 C11 C12 119.6(2) . .
C10 C11 C18 117.2(2) . .
C12 C11 C18 122.9(2) . .
C13 C12 C17 118.6(2) . .
C13 C12 C11 122.1(2) . .
C17 C12 C11 119.2(2) . .
C14 C13 C12 121.1(3) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C13 C14 C15 120.2(3) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 120.7(3) . .
C16 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
C15 C16 C17 121.4(3) . .
C15 C16 H16 119.3 . .
C17 C16 H16 119.3 . .
C16 C17 C12 117.9(2) . .
C16 C17 C8 123.2(2) . .
C12 C17 C8 118.9(2) . .
O4 C18 O3 124.9(2) . .
O4 C18 C11 117.1(2) . .
O3 C18 C11 117.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.327(3) .
N1 C1 1.335(3) .
N1 Zn1 2.043(2) .
N2 C6 1.236(4) .
N2 N2 1.396(5) 2_654
O1 C7 1.261(3) .
O1 Zn1 2.0113(18) .
O2 C7 1.254(3) .
O2 Zn1 2.0447(18) 2_655
O3 C18 1.256(3) .
O3 Zn1 2.0851(18) 4_645
O4 C18 1.249(3) .
O4 Zn1 2.0280(18) 3_545
O5 H5A 0.8500 .
O5 H5B 0.8500 .
Zn1 O4 2.0280(18) 3_455
Zn1 O2 2.0447(18) 2_655
Zn1 O3 2.0851(18) 4_655
Zn1 Zn1 2.9884(6) 2_655
C1 C2 1.381(4) .
C1 H1 0.9300 .
C2 C3 1.379(4) .
C2 C6 1.460(4) .
C3 C4 1.368(4) .
C3 H3 0.9300 .
C4 C5 1.378(4) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.513(3) .
C8 C9 1.365(4) .
C8 C17 1.437(3) .
C9 C10 1.395(4) .
C9 H9 0.9300 .
C10 C11 1.368(3) .
C10 H10 0.9300 .
C11 C12 1.428(3) .
C11 C18 1.506(3) .
C12 C13 1.422(3) .
C12 C17 1.425(3) .
C13 C14 1.361(4) .
C13 H13 0.9300 .
C14 C15 1.390(4) .
C14 H14 0.9300 .
C15 C16 1.361(4) .
C15 H15 0.9300 .
C16 C17 1.417(4) .
C16 H16 0.9300 .
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
C7 O1 Zn1 O4 -4.2(3) . 3_455
C7 O1 Zn1 N1 163.8(2) . .
C7 O1 Zn1 O2 -88.4(2) . 2_655
C7 O1 Zn1 O3 71.4(2) . 4_655
C7 O1 Zn1 Zn1 -11.8(2) . 2_655
C5 N1 Zn1 O1 162.7(2) . .
C1 N1 Zn1 O1 -32.0(2) . .
C5 N1 Zn1 O4 -22.1(2) . 3_455
C1 N1 Zn1 O4 143.2(2) . 3_455
C5 N1 Zn1 O2 63.9(2) . 2_655
C1 N1 Zn1 O2 -130.8(2) . 2_655
C5 N1 Zn1 O3 -111.1(2) . 4_655
C1 N1 Zn1 O3 54.2(2) . 4_655
C5 N1 Zn1 Zn1 -50.6(5) . 2_655
C1 N1 Zn1 Zn1 114.7(4) . 2_655
C5 N1 C1 C2 2.1(4) . .
Zn1 N1 C1 C2 -163.6(2) . .
N1 C1 C2 C3 -2.1(5) . .
N1 C1 C2 C6 175.6(3) . .
C1 C2 C3 C4 0.4(5) . .
C6 C2 C3 C4 -177.2(3) . .
C2 C3 C4 C5 1.2(5) . .
C1 N1 C5 C4 -0.3(5) . .
Zn1 N1 C5 C4 165.5(3) . .
C3 C4 C5 N1 -1.3(5) . .
N2 N2 C6 C2 173.9(3) 2_654 .
C3 C2 C6 N2 -3.8(6) . .
C1 C2 C6 N2 178.7(4) . .
Zn1 O2 C7 O1 -24.4(4) 2_655 .
Zn1 O2 C7 C8 155.20(18) 2_655 .
Zn1 O1 C7 O2 24.7(4) . .
Zn1 O1 C7 C8 -154.91(18) . .
O2 C7 C8 C9 30.8(4) . .
O1 C7 C8 C9 -149.6(3) . .
O2 C7 C8 C17 -147.1(3) . .
O1 C7 C8 C17 32.5(4) . .
C17 C8 C9 C10 -3.0(4) . .
C7 C8 C9 C10 178.9(3) . .
C8 C9 C10 C11 0.4(5) . .
C9 C10 C11 C12 3.4(4) . .
C9 C10 C11 C18 -170.1(3) . .
C10 C11 C12 C13 173.1(3) . .
C18 C11 C12 C13 -13.8(4) . .
C10 C11 C12 C17 -4.5(4) . .
C18 C11 C12 C17 168.6(2) . .
C17 C12 C13 C14 -2.4(4) . .
C11 C12 C13 C14 179.9(3) . .
C12 C13 C14 C15 0.7(5) . .
C13 C14 C15 C16 1.1(6) . .
C14 C15 C16 C17 -1.1(6) . .
C15 C16 C17 C12 -0.6(5) . .
C15 C16 C17 C8 177.4(3) . .
C13 C12 C17 C16 2.3(4) . .
C11 C12 C17 C16 -179.9(3) . .
C13 C12 C17 C8 -175.8(2) . .
C11 C12 C17 C8 1.9(4) . .
C9 C8 C17 C16 -176.2(3) . .
C7 C8 C17 C16 1.6(4) . .
C9 C8 C17 C12 1.8(4) . .
C7 C8 C17 C12 179.7(2) . .
Zn1 O4 C18 O3 9.8(5) 3_545 .
Zn1 O4 C18 C11 -165.29(19) 3_545 .
Zn1 O3 C18 O4 -6.5(4) 4_645 .
Zn1 O3 C18 C11 168.57(17) 4_645 .
C10 C11 C18 O4 142.8(3) . .
C12 C11 C18 O4 -30.5(4) . .
C10 C11 C18 O3 -32.7(4) . .
C12 C11 C18 O3 154.1(3) . .
