#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/06/4000679.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_4000679
loop_
_publ_author_name
'Hyunsoo Park'
'David M. Moureau'
'John B. Parise'
_publ_section_title
;
 Hydrothermal Synthesis and Structural Characterization of Novel
 Zn-Triazole-Benzenedicarboxylate Frameworks
;
_journal_issue                   2
_journal_name_full               'Chem. Mater.'
_journal_page_first              525
_journal_page_last               531
_journal_paper_doi               10.1021/cm051829l
_journal_volume                  18
_journal_year                    2006
_chemical_formula_sum            'C24 H16 N12 O24 Zn4'
_chemical_formula_weight         1117.97
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.475(3)
_cell_length_b                   26.949(5)
_cell_length_c                   13.509(3)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.90
_cell_measurement_theta_min      1.04
_cell_volume                     4885.7(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Endeavor 1.1'
_computing_publication_material  'SHELXL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXS (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.48595
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            58520
_diffrn_reflns_theta_full        18.90
_diffrn_reflns_theta_max         18.90
_diffrn_reflns_theta_min         1.04
_diffrn_source                   synchrotron
_diffrn_source_type              'APS 15-ID'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2224
_exptl_crystal_recrystallization_method hydrothermal
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.881
_refine_diff_density_min         -1.420
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         11818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0681P)²+28.5757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                10797
_reflns_number_total             11818
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4000679
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Zn1 Zn 0.77812(5) 1.02402(2) 0.13763(4) 0.01558(13) Uani 1 1 d .
Zn2 Zn 0.63289(4) 0.94572(2) -0.25738(4) 0.01451(12) Uani 1 1 d .
Zn3 Zn 0.74235(4) 0.92425(2) 0.31569(4) 0.01341(12) Uani 1 1 d .
Zn4 Zn 0.81109(5) 1.04392(2) -0.29313(4) 0.01542(13) Uani 1 1 d .
N1 N 0.4994(3) 0.97580(16) -0.2471(3) 0.0177(9) Uani 1 1 d .
N2 N 0.7860(3) 0.99838(17) 0.0009(3) 0.0175(8) Uani 1 1 d .
N3 N 0.7369(3) 0.94906(16) 0.4631(3) 0.0166(8) Uani 1 1 d .
N4 N 0.6340(3) 0.97524(16) 0.2661(3) 0.0172(8) Uani 1 1 d .
N5 N 0.8743(3) 0.96106(17) 0.2979(3) 0.0177(9) Uani 1 1 d .
N6 N 0.6889(3) 0.95945(16) -0.3858(3) 0.0159(8) Uani 1 1 d .
N7 N 0.6473(4) 1.00991(17) 0.1922(3) 0.0199(9) Uani 1 1 d .
N8 N 0.7270(3) 0.97090(16) -0.1466(3) 0.0180(9) Uani 1 1 d .
N9 N 0.7972(3) 1.00712(17) -0.1602(3) 0.0178(8) Uani 1 1 d .
N10 N 0.9627(3) 1.02442(18) -0.2978(3) 0.0193(9) Uani 1 1 d .
N11 N 0.7557(3) 0.99642(15) -0.4026(3) 0.0150(8) Uani 1 1 d .
N12 N 0.8870(3) 0.99965(16) 0.2337(3) 0.0155(8) Uani 1 1 d .
O1 O 0.7429(3) 0.90120(16) 0.1627(3) 0.0280(9) Uani 1 1 d .
O2 O 0.7313(6) 1.0952(2) 0.1096(7) 0.089(3) Uani 1 1 d .
O3 O 0.6259(4) 0.87345(14) -0.2711(3) 0.0315(10) Uani 1 1 d .
O4 O 0.6552(3) 0.85934(14) 0.3443(3) 0.0255(9) Uani 1 1 d .
O5 O 0.8186(4) 0.85351(16) 0.3711(4) 0.0335(10) Uani 1 1 d .
O6 O 0.6600(3) 1.06760(17) -0.2703(3) 0.0296(9) Uani 1 1 d .
O7 O 0.8325(3) 1.11258(15) -0.3512(4) 0.0301(10) Uani 1 1 d .
O8 O 0.5799(3) 0.87101(15) -0.1182(3) 0.0269(9) Uani 1 1 d .
O9 O 0.8873(4) 1.11589(16) -0.1923(4) 0.0411(13) Uani 1 1 d .
O10 O 0.8947(6) 1.1010(2) 0.0998(5) 0.065(2) Uani 1 1 d .
C1 C 0.7949(6) 1.1765(2) 0.1011(5) 0.0366(16) Uani 1 1 d .
C2 C 0.9655(4) 0.9478(2) 0.3340(4) 0.0192(10) Uani 1 1 d .
H2 H 0.9788 0.9216 0.3803 0.023 Uiso 1 1 calc R
C3 C 0.6802(4) 0.9319(2) 0.5322(4) 0.0177(10) Uani 1 1 d .
H3 H 0.6387 0.9034 0.5236 0.021 Uiso 1 1 calc R
C4 C 0.7815(4) 0.98927(19) 0.5069(4) 0.0182(10) Uani 1 1 d .
H4 H 0.8264 1.0101 0.4759 0.022 Uiso 1 1 calc R
C5 C 0.4543(4) 1.01396(19) -0.2967(4) 0.0182(10) Uani 1 1 d .
H5 H 0.4827 1.0314 -0.3483 0.022 Uiso 1 1 calc R
C6 C 0.7235(5) 0.7790(2) 0.3837(4) 0.0254(12) Uani 1 1 d .
C7 C 0.7230(4) 0.96727(19) -0.0503(4) 0.0171(10) Uani 1 1 d .
H7 H 0.6802 0.9450 -0.0201 0.021 Uiso 1 1 calc R
C8 C 0.8305(4) 1.0225(2) -0.0715(4) 0.0196(10) Uani 1 1 d .
H8 H 0.8797 1.0475 -0.0592 0.024 Uiso 1 1 calc R
C9 C 0.5661(4) 1.0374(2) 0.1834(4) 0.0205(10) Uani 1 1 d .
H9 H 0.5553 1.0638 0.1369 0.025 Uiso 1 1 calc R
C10 C 0.7341(5) 0.8336(2) 0.3662(4) 0.0252(12) Uani 1 1 d .
C11 C 1.0153(4) 0.9931(2) -0.2357(4) 0.0201(10) Uani 1 1 d .
H11 H 0.9857 0.9684 -0.1974 0.024 Uiso 1 1 calc R
C12 C 0.6042(4) 0.79445(19) -0.2018(4) 0.0227(11) Uani 1 1 d .
C13 C 0.8800(5) 1.1916(2) -0.2835(5) 0.0268(12) Uani 1 1 d .
C14 C 0.6012(4) 0.8496(2) -0.1946(4) 0.0198(10) Uani 1 1 d .
C15 C 0.8667(5) 1.1363(2) -0.2728(5) 0.0289(14) Uani 1 1 d .
C16 C 0.6042(6) 0.7719(2) -0.2946(5) 0.0351(14) Uani 1 1 d .
H16 H 0.5996 0.7916 -0.3533 0.042 Uiso 1 1 calc R
C17 C 0.8084(6) 0.7490(2) 0.3875(6) 0.0374(15) Uani 1 1 d .
H17 H 0.8726 0.7634 0.3852 0.045 Uiso 1 1 calc R
C18 C 0.6111(6) 0.7201(2) -0.3009(5) 0.0352(15) Uani 1 1 d .
H18 H 0.6096 0.7046 -0.3642 0.042 Uiso 1 1 calc R
C19 C 0.7977(6) 0.6975(3) 0.3947(6) 0.0428(18) Uani 1 1 d .
H19 H 0.8550 0.6768 0.3967 0.051 Uiso 1 1 calc R
C20 C 0.6314(6) 0.7575(2) 0.3923(6) 0.0385(16) Uani 1 1 d .
H20 H 0.5740 0.7779 0.3926 0.046 Uiso 1 1 calc R
C21 C 0.6108(7) 0.7647(2) -0.1177(5) 0.0397(18) Uani 1 1 d .
H21 H 0.6072 0.7795 -0.0543 0.048 Uiso 1 1 calc R
C22 C 0.6219(6) 0.7060(2) 0.4004(6) 0.0401(17) Uani 1 1 d .
H22 H 0.5586 0.6915 0.4068 0.048 Uiso 1 1 calc R
C23 C 0.8069(8) 1.1202(3) 0.1050(6) 0.047(2) Uani 1 1 d .
C24 C 0.6225(7) 0.7138(2) -0.1247(6) 0.0408(18) Uani 1 1 d .
H24 H 0.6322 0.6942 -0.0661 0.049 Uiso 1 1 calc R
O11 O 0.5671(5) 0.8551(2) 0.0804(4) 0.0442(13) Uani 1 1 d .
O12 O 0.9440(5) 0.8374(3) 0.5554(5) 0.0597(16) Uani 1 1 d .
O13 O 0.6028(5) 0.0793(2) 0.9213(5) 0.0584(17) Uani 1 1 d .
O14 O 0.5541(6) 0.1433(4) 0.6377(8) 0.109(4) Uani 1 1 d .
O15 O 0.9149(5) 0.8630(3) 0.0897(5) 0.0633(19) Uani 1 1 d .
O16 O 0.8330(5) 0.8404(3) 0.7217(5) 0.0634(18) Uani 1 1 d .
O17 O 0.5203(7) 0.7554(3) 0.1373(7) 0.086(3) Uani 1 1 d .
O18 O 0.0829(7) 0.1086(3) 0.1061(6) 0.084(3) Uani 1 1 d .
O19 O 0.8850(7) 0.7489(4) 0.8125(9) 0.111(4) Uani 1 1 d .
O20 O 0.1121(7) 0.9002(3) 0.5474(6) 0.079(2) Uani 1 1 d .
O21 O 0.8744(8) 0.7620(4) 0.0299(8) 0.106(3) Uani 1 1 d .
O22 O 0.2826(8) 0.8740(4) 0.6652(8) 0.112(3) Uani 1 1 d .
O23 O 0.7214(9) 0.7269(4) 0.1308(8) 0.111(3) Uani 1 1 d .
O24 O 0.5653(10) 0.1581(6) 0.4414(10) 0.149(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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3242 0.9375 '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
N12 Zn1 N2 113.31(19) . .
N12 Zn1 N7 108.65(18) . .
N2 Zn1 N7 113.5(2) . .
N12 Zn1 O2 129.1(3) . .
N2 Zn1 O2 101.3(3) . .
N7 Zn1 O2 88.8(2) . .
O3 Zn2 N6 96.97(18) . .
O3 Zn2 N1 112.1(2) . .
N6 Zn2 N1 113.72(19) . .
O3 Zn2 N8 115.6(2) . .
N6 Zn2 N8 109.03(18) . .
N1 Zn2 N8 109.09(19) . .
N5 Zn3 N4 103.44(18) . .
N5 Zn3 N3 93.49(17) . .
N4 Zn3 N3 90.64(18) . .
N5 Zn3 O1 87.13(18) . .
N4 Zn3 O1 86.82(17) . .
N3 Zn3 O1 177.46(17) . .
N5 Zn3 O4 153.59(18) . .
N4 Zn3 O4 102.46(17) . .
N3 Zn3 O4 91.25(16) . .
O1 Zn3 O4 89.27(16) . .
N5 Zn3 O5 94.19(17) . .
N4 Zn3 O5 162.23(17) . .
N3 Zn3 O5 90.47(17) . .
O1 Zn3 O5 91.94(17) . .
O4 Zn3 O5 59.78(17) . .
N5 Zn3 C10 123.4(2) . .
N4 Zn3 C10 132.7(2) . .
N3 Zn3 C10 92.59(17) . .
O1 Zn3 C10 89.12(17) . .
O4 Zn3 C10 30.29(19) . .
O5 Zn3 C10 29.57(19) . .
O7 Zn4 N11 110.15(19) . .
O7 Zn4 N9 142.49(19) . .
N11 Zn4 N9 105.74(18) . .
O7 Zn4 N10 92.47(18) . .
N11 Zn4 N10 96.49(18) . .
N9 Zn4 N10 94.02(18) . .
O7 Zn4 O6 87.44(17) . .
N11 Zn4 O6 90.05(18) . .
N9 Zn4 O6 81.92(18) . .
N10 Zn4 O6 173.05(18) . .
C9 N1 C5 103.4(4) 3_675 .
C9 N1 Zn2 126.2(4) 3_675 .
C5 N1 Zn2 130.4(4) . .
C7 N2 C8 103.2(4) . .
C7 N2 Zn1 127.9(3) . .
C8 N2 Zn1 124.6(4) . .
C3 N3 C4 103.3(4) . .
C3 N3 Zn3 128.2(4) . .
C4 N3 Zn3 128.1(3) . .
C5 N4 N7 104.7(4) 3_675 .
C5 N4 Zn3 132.1(4) 3_675 .
N7 N4 Zn3 123.0(3) . .
C2 N5 N12 105.6(4) . .
C2 N5 Zn3 127.2(3) . .
N12 N5 Zn3 126.4(4) . .
C3 N6 N11 106.0(4) 1_554 .
C3 N6 Zn2 127.7(3) 1_554 .
N11 N6 Zn2 125.8(3) . .
C9 N7 N4 106.5(4) . .
C9 N7 Zn1 127.5(4) . .
N4 N7 Zn1 124.4(3) . .
C7 N8 N9 105.9(4) . .
C7 N8 Zn2 129.8(4) . .
N9 N8 Zn2 122.5(3) . .
C8 N9 N8 106.5(4) . .
C8 N9 Zn4 126.2(4) . .
N8 N9 Zn4 124.7(4) . .
C11 N10 C2 102.7(5) . 3_775
C11 N10 Zn4 126.3(4) . .
C2 N10 Zn4 126.8(4) 3_775 .
C4 N11 N6 106.2(4) 1_554 .
C4 N11 Zn4 130.9(4) 1_554 .
N6 N11 Zn4 122.3(3) . .
C11 N12 N5 106.2(4) 3_775 .
C11 N12 Zn1 129.6(4) 3_775 .
N5 N12 Zn1 122.5(3) . .
C23 O2 Zn1 106.3(7) . .
C14 O3 Zn2 115.8(4) . .
C10 O4 Zn3 91.4(3) . .
C10 O5 Zn3 87.7(4) . .
C15 O7 Zn4 100.8(4) . .
C22 C1 C19 120.4(6) 2_655 2_655
C22 C1 C23 119.4(7) 2_655 .
C19 C1 C23 120.1(7) 2_655 .
N5 C2 N10 112.9(5) . 3_775
N6 C3 N3 112.0(4) 1_556 .
N11 C4 N3 112.4(4) 1_556 .
N4 C5 N1 113.0(4) 3_675 .
C20 C6 C17 119.4(6) . .
C20 C6 C10 121.6(6) . .
C17 C6 C10 119.0(6) . .
N8 C7 N2 112.7(4) . .
N9 C8 N2 111.8(5) . .
N7 C9 N1 112.5(5) . 3_675
O5 C10 O4 120.8(5) . .
O5 C10 C6 120.6(6) . .
O4 C10 C6 118.5(5) . .
O5 C10 Zn3 62.8(3) . .
O4 C10 Zn3 58.3(3) . .
C6 C10 Zn3 173.1(4) . .
N12 C11 N10 112.6(4) 3_775 .
C21 C12 C16 118.7(5) . .
C21 C12 C14 121.6(5) . .
C16 C12 C14 119.6(5) . .
C18 C13 C24 120.1(6) 2_654 2_654
C18 C13 C15 118.4(6) 2_654 .
C24 C13 C15 121.4(6) 2_654 .
O8 C14 O3 122.3(5) . .
O8 C14 C12 121.9(5) . .
O3 C14 C12 115.8(5) . .
O9 C15 O7 122.8(6) . .
O9 C15 C13 120.5(6) . .
O7 C15 C13 116.7(6) . .
C12 C16 C18 119.5(6) . .
C6 C17 C19 119.1(7) . .
C13 C18 C16 120.6(6) 2_644 .
C1 C19 C17 120.7(7) 2_645 .
C6 C20 C22 120.8(7) . .
C24 C21 C12 121.1(6) . .
C1 C22 C20 119.4(7) 2_645 .
O2 C23 O10 123.2(7) . .
O2 C23 C1 117.5(9) . .
O10 C23 C1 119.2(7) . .
C13 C24 C21 119.9(7) 2_644 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N12 1.981(5) .
Zn1 N2 1.983(4) .
Zn1 N7 2.008(5) .
Zn1 O2 2.044(7) .
Zn2 O3 1.958(4) .
Zn2 N6 1.988(4) .
Zn2 N1 1.990(4) .
Zn2 N8 1.991(5) .
Zn3 N5 2.068(4) .
Zn3 N4 2.072(4) .
Zn3 N3 2.108(4) .
Zn3 O1 2.158(4) .
Zn3 O4 2.161(4) .
Zn3 O5 2.261(5) .
Zn3 C10 2.540(5) .
Zn4 O7 2.041(4) .
Zn4 N11 2.046(4) .
Zn4 N9 2.075(4) .
Zn4 N10 2.116(5) .
Zn4 O6 2.182(4) .
N1 C9 1.335(6) 3_675
N1 C5 1.343(7) .
N2 C7 1.340(7) .
N2 C8 1.358(6) .
N3 C3 1.341(6) .
N3 C4 1.350(7) .
N4 C5 1.326(7) 3_675
N4 N7 1.391(6) .
N5 C2 1.330(7) .
N5 N12 1.375(6) .
N6 C3 1.331(7) 1_554
N6 N11 1.375(6) .
N7 C9 1.318(7) .
N8 C7 1.310(7) .
N8 N9 1.383(6) .
N9 C8 1.309(7) .
N10 C11 1.347(7) .
N10 C2 1.348(6) 3_775
N11 C4 1.314(7) 1_554
N12 C11 1.329(7) 3_775
O2 C23 1.227(11) .
O3 C14 1.286(7) .
O4 C10 1.282(8) .
O5 C10 1.255(8) .
O7 C15 1.286(8) .
O8 C14 1.239(7) .
O9 C15 1.228(8) .
O10 C23 1.300(12) .
C1 C22 1.376(10) 2_655
C1 C19 1.376(11) 2_655
C1 C23 1.527(9) .
C2 N10 1.348(6) 3_775
C3 N6 1.331(7) 1_556
C4 N11 1.314(7) 1_556
C5 N4 1.326(7) 3_675
C6 C20 1.385(9) .
C6 C17 1.398(9) .
C6 C10 1.500(7) .
C9 N1 1.335(6) 3_675
C11 N12 1.329(7) 3_775
C12 C21 1.386(9) .
C12 C16 1.393(9) .
C12 C14 1.491(7) .
C13 C18 1.370(9) 2_654
C13 C24 1.374(10) 2_654
C13 C15 1.511(8) .
C16 C18 1.404(9) .
C17 C19 1.400(9) .
C18 C13 1.370(9) 2_644
C19 C1 1.376(11) 2_645
C20 C22 1.398(9) .
C21 C24 1.385(8) .
C22 C1 1.376(10) 2_645
C24 C13 1.374(10) 2_644
