#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:46:33 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/71/7227144.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_7227144
loop_
_publ_author_name
'Gu, Jin-Zhong'
'Liang, Xiao-Xiao'
'Cui, Yan-Hui'
'Wu, Jiang'
'Kirillov, Alexander M.'
_publ_section_title
;
 Exploring 4-(3-carboxyphenyl)picolinic acid as a semirigid building block
 for the hydrothermal self-assembly of diverse metal--organic and
 supramolecular networks
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              117
_journal_paper_doi               10.1039/C6CE02115H
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C26 H20 N2 O10 Zn, 2(H2 O)'
_chemical_formula_sum            'C26 H24 N2 O12 Zn'
_chemical_formula_weight         621.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.40(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.523(4)
_cell_length_b                   14.220(3)
_cell_length_c                   7.0884(19)
_cell_measurement_reflns_used    359
_cell_measurement_temperature    295.69(16)
_cell_measurement_theta_max      26.4900
_cell_measurement_theta_min      4.3260
_cell_volume                     1260.1(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.69(16)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   89.60   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   24.20   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.0420  -99.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -50.00   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.0420  -57.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00  110.60   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  178.0000  150.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0102741000
_diffrn_orient_matrix_UB_12      -0.0483346000
_diffrn_orient_matrix_UB_13      0.0163525000
_diffrn_orient_matrix_UB_21      -0.0553442000
_diffrn_orient_matrix_UB_22      0.0099537000
_diffrn_orient_matrix_UB_23      0.0031027000
_diffrn_orient_matrix_UB_31      -0.0067855000
_diffrn_orient_matrix_UB_32      -0.0076769000
_diffrn_orient_matrix_UB_33      -0.0988506000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1183
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3635
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02115h1.cif
_cod_data_source_block           compound_2
_cod_depositor_comments
'Adding full bibliography for 7227139--7227149.cif.'
_cod_database_code               7227144
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.5000 0.5000 0.5000 0.0247(3) Uani 1 2 d S T P
O1 O 0.4392(3) 0.3850(2) 0.6236(5) 0.0209(8) Uani 1 1 d . . .
O2 O 0.4853(2) 0.2543(3) 0.7782(5) 0.0256(9) Uani 1 1 d . . .
O3 O 1.2090(3) 0.3526(3) 0.7885(6) 0.0407(12) Uani 1 1 d . . .
O4 O 1.2778(3) 0.2081(3) 0.7721(6) 0.0417(12) Uani 1 1 d . . .
H4 H 1.3351 0.2359 0.7861 0.063 Uiso 1 1 calc GR . .
O5 O 0.5022(3) 0.5657(3) 0.7673(5) 0.0274(8) Uani 1 1 d D . .
H5A H 0.5552 0.5441 0.8419 0.041 Uiso 1 1 d DGR . .
N1 N 0.6376(3) 0.4323(3) 0.5729(5) 0.0175(10) Uani 1 1 d . . .
C1 C 0.5064(4) 0.3265(3) 0.6852(6) 0.0169(11) Uani 1 1 d . . .
C2 C 0.6223(4) 0.3464(3) 0.6505(7) 0.0144(11) Uani 1 1 d . . .
C3 C 0.7058(4) 0.2857(3) 0.6898(7) 0.0171(12) Uani 1 1 d . . .
H3 H 0.6937 0.2272 0.7431 0.020 Uiso 1 1 calc R . .
C4 C 0.8082(4) 0.3124(4) 0.6493(7) 0.0174(12) Uani 1 1 d . . .
C5 C 0.8223(4) 0.4013(4) 0.5764(7) 0.0200(12) Uani 1 1 d . . .
H5 H 0.8905 0.4219 0.5515 0.024 Uiso 1 1 calc R . .
C6 C 0.7357(4) 0.4593(4) 0.5406(7) 0.0208(12) Uani 1 1 d . . .
H6 H 0.7466 0.5192 0.4924 0.025 Uiso 1 1 calc R . .
C7 C 0.9013(4) 0.2464(4) 0.6733(8) 0.0185(12) Uani 1 1 d . . .
C8 C 1.0032(4) 0.2816(4) 0.7142(8) 0.0217(14) Uani 1 1 d . . .
H8 H 1.0120 0.3459 0.7332 0.026 Uiso 1 1 calc R . .
C9 C 1.0917(4) 0.2241(4) 0.7274(8) 0.0240(14) Uani 1 1 d . . .
C10 C 1.0773(4) 0.1279(4) 0.7014(8) 0.0283(14) Uani 1 1 d . . .
H10 H 1.1363 0.0880 0.7079 0.034 Uiso 1 1 calc R . .
C11 C 0.9775(4) 0.0917(4) 0.6664(8) 0.0249(14) Uani 1 1 d . . .
H11 H 0.9688 0.0271 0.6530 0.030 Uiso 1 1 calc R . .
C12 C 0.8888(4) 0.1501(4) 0.6506(7) 0.0227(13) Uani 1 1 d . . .
H12 H 0.8210 0.1248 0.6249 0.027 Uiso 1 1 calc R . .
C13 C 1.1993(4) 0.2692(4) 0.7648(8) 0.0287(15) Uani 1 1 d . . .
O6 O 0.3365(3) 0.4945(3) 0.9730(6) 0.0395(10) Uani 1 1 d . . .
H6A H 0.3093 0.4441 0.9268 0.059 Uiso 1 1 d G . .
H6B H 0.3791 0.5177 0.8965 0.059 Uiso 1 1 d DG . .
H5B H 0.500(4) 0.6245(11) 0.747(7) 0.05(2) Uiso 1 1 d 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_
_diffrn_radiation_monochromator
mirror
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
O1 Zn1 O1 180.00(18) . 3_666
O1 Zn1 O5 92.61(15) 3_666 .
O1 Zn1 O5 87.39(15) . .
O1 Zn1 O5 87.38(15) 3_666 3_666
O1 Zn1 O5 92.61(15) . 3_666
O5 Zn1 O5 180.0 3_666 .
N1 Zn1 O1 99.16(14) 3_666 .
N1 Zn1 O1 80.84(14) . .
N1 Zn1 O1 99.16(14) . 3_666
N1 Zn1 O1 80.84(14) 3_666 3_666
N1 Zn1 O5 89.11(15) 3_666 .
N1 Zn1 O5 90.89(15) . .
N1 Zn1 O5 90.89(15) 3_666 3_666
N1 Zn1 O5 89.11(15) . 3_666
N1 Zn1 N1 180.0 . 3_666
C1 O1 Zn1 115.4(3) . .
C13 O4 H4 109.5 . .
Zn1 O5 H5A 110.8 . .
Zn1 O5 H5B 106(4) . .
H5A O5 H5B 117.4 . .
C2 N1 Zn1 113.3(3) . .
C6 N1 Zn1 127.4(3) . .
C6 N1 C2 119.1(4) . .
O1 C1 O2 124.9(5) . .
O1 C1 C2 116.9(4) . .
O2 C1 C2 118.1(4) . .
N1 C2 C1 113.2(4) . .
N1 C2 C3 121.6(5) . .
C3 C2 C1 125.2(5) . .
C2 C3 H3 120.3 . .
C2 C3 C4 119.3(5) . .
C4 C3 H3 120.3 . .
C3 C4 C7 122.0(5) . .
C5 C4 C3 118.0(5) . .
C5 C4 C7 120.0(5) . .
C4 C5 H5 119.9 . .
C6 C5 C4 120.1(5) . .
C6 C5 H5 119.9 . .
N1 C6 C5 121.7(5) . .
N1 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
C8 C7 C4 119.9(5) . .
C8 C7 C12 118.6(5) . .
C12 C7 C4 121.5(5) . .
C7 C8 H8 119.1 . .
C9 C8 C7 121.8(5) . .
C9 C8 H8 119.1 . .
C8 C9 C10 118.5(5) . .
C8 C9 C13 118.0(5) . .
C10 C9 C13 123.4(5) . .
C9 C10 H10 119.8 . .
C11 C10 C9 120.4(5) . .
C11 C10 H10 119.8 . .
C10 C11 H11 119.6 . .
C10 C11 C12 120.8(5) . .
C12 C11 H11 119.6 . .
C7 C12 H12 120.1 . .
C11 C12 C7 119.8(5) . .
C11 C12 H12 120.1 . .
O3 C13 O4 125.4(6) . .
O3 C13 C9 121.8(5) . .
O4 C13 C9 112.8(5) . .
H6A O6 H6B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.024(3) .
Zn1 O1 2.025(3) 3_666
Zn1 O5 2.111(3) .
Zn1 O5 2.111(3) 3_666
Zn1 N1 2.014(4) 3_666
Zn1 N1 2.014(4) .
O1 C1 1.244(5) .
O2 C1 1.257(5) .
O3 C13 1.203(6) .
O4 H4 0.8200 .
O4 C13 1.311(6) .
O5 H5A 0.8793 .
O5 H5B 0.849(12) .
N1 C2 1.358(6) .
N1 C6 1.321(6) .
C1 C2 1.514(7) .
C2 C3 1.372(6) .
C3 H3 0.9300 .
C3 C4 1.383(6) .
C4 C5 1.381(7) .
C4 C7 1.499(7) .
C5 H5 0.9300 .
C5 C6 1.374(7) .
C6 H6 0.9300 .
C7 C8 1.384(6) .
C7 C12 1.386(7) .
C8 H8 0.9300 .
C8 C9 1.377(6) .
C9 C10 1.391(7) .
C9 C13 1.501(7) .
C10 H10 0.9300 .
C10 C11 1.360(7) .
C11 H11 0.9300 .
C11 C12 1.387(7) .
C12 H12 0.9300 .
O6 H6A 0.8504 .
O6 H6B 0.8498 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.82 1.90 2.678(5) 157.2 1_655
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
Zn1 O1 C1 O2 174.6(4)
Zn1 O1 C1 C2 -3.2(5)
Zn1 N1 C2 C1 -6.8(5)
Zn1 N1 C2 C3 172.7(4)
Zn1 N1 C6 C5 -171.7(4)
O1 C1 C2 N1 6.8(6)
O1 C1 C2 C3 -172.7(5)
O2 C1 C2 N1 -171.1(4)
O2 C1 C2 C3 9.4(7)
N1 C2 C3 C4 -0.1(7)
C1 C2 C3 C4 179.4(4)
C2 N1 C6 C5 2.6(7)
C2 C3 C4 C5 2.2(7)
C2 C3 C4 C7 -174.7(5)
C3 C4 C5 C6 -2.0(7)
C3 C4 C7 C8 -151.4(5)
C3 C4 C7 C12 30.4(8)
C4 C5 C6 N1 -0.5(8)
C4 C7 C8 C9 -176.5(5)
C4 C7 C12 C11 177.4(5)
C5 C4 C7 C8 31.8(8)
C5 C4 C7 C12 -146.5(5)
C6 N1 C2 C1 178.1(4)
C6 N1 C2 C3 -2.4(7)
C7 C4 C5 C6 175.0(5)
C7 C8 C9 C10 -0.9(9)
C7 C8 C9 C13 177.7(5)
C8 C7 C12 C11 -0.9(8)
C8 C9 C10 C11 -0.9(9)
C8 C9 C13 O3 2.2(8)
C8 C9 C13 O4 -179.2(5)
C9 C10 C11 C12 1.9(9)
C10 C9 C13 O3 -179.2(6)
C10 C9 C13 O4 -0.6(8)
C10 C11 C12 C7 -0.9(9)
C12 C7 C8 C9 1.9(9)
C13 C9 C10 C11 -179.5(5)
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4328(17)
2 0.5672(17)
