#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/11/4501155.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_4501155
loop_
_publ_author_name
'Hogan, Greg A.'
'Rath, Nigam P.'
'Beatty, Alicia M.'
_publ_section_title
;
 A Stable Hydrogen-Bonded Coordination Network with Removable Guests
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3740
_journal_paper_doi               10.1021/cg200793f
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C14 H10 N2 O10 Zn, C14 H18 N2, C6 H14 O'
_chemical_formula_sum            'C34 H42 N4 O11 Zn'
_chemical_formula_weight         748.09
_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                91.072(9)
_cell_angle_beta                 96.028(9)
_cell_angle_gamma                99.886(8)
_cell_formula_units_Z            1
_cell_length_a                   5.2571(8)
_cell_length_b                   8.2727(13)
_cell_length_c                   19.632(4)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.75
_cell_volume                     835.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5710
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.7368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.707
_refine_diff_density_min         -1.742
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0834
_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)+(0.1506P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2107
_refine_ls_wR_factor_ref         0.2266
_reflns_number_gt                2789
_reflns_number_total             3632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200793f_si_002.cif
_cod_data_source_block           2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        835.9(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501155
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.0000 1.0000 0.0000 0.0174(3) Uani 1 2 d S . .
O1 O 0.7632(6) 1.0163(4) 0.07782(15) 0.0199(7) Uani 1 1 d . . .
O2 O 0.6368(6) 0.8933(4) 0.17149(15) 0.0202(7) Uani 1 1 d . . .
O3 O 1.3256(6) 1.1505(4) 0.05955(16) 0.0190(6) Uani 1 1 d D . .
H3A H 1.311(11) 1.193(6) 0.099(2) 0.026(14) Uiso 1 1 d D . .
H3B H 1.462(9) 1.104(6) 0.070(3) 0.030(14) Uiso 1 1 d D . .
O4 O 1.0122(7) 0.4037(4) 0.24541(17) 0.0276(8) Uani 1 1 d . . .
O5 O 1.2647(7) 0.2988(4) 0.17872(16) 0.0280(8) Uani 1 1 d . . .
N1 N 1.0611(6) 0.7918(4) 0.05497(18) 0.0172(7) Uani 1 1 d . . .
N2 N 0.6096(7) 1.1541(5) 0.25872(18) 0.0211(8) Uani 1 1 d . . .
H2A H 0.6233 1.0636 0.2332 0.032 Uiso 1 1 calc R . .
H2B H 0.7551 1.2311 0.2578 0.032 Uiso 1 1 calc R . .
H2C H 0.4683 1.1957 0.2411 0.032 Uiso 1 1 calc R . .
C1 C 0.7595(7) 0.9023(5) 0.1213(2) 0.0171(8) Uani 1 1 d . . .
C2 C 0.9248(7) 0.7735(5) 0.1094(2) 0.0163(8) Uani 1 1 d . . .
C3 C 0.9351(8) 0.6481(5) 0.1535(2) 0.0185(9) Uani 1 1 d . . .
H3 H 0.8323 0.6377 0.1907 0.022 Uiso 1 1 calc R . .
C4 C 1.0995(8) 0.5350(5) 0.1430(2) 0.0186(9) Uani 1 1 d . . .
C5 C 1.2378(8) 0.5542(5) 0.0865(2) 0.0186(9) Uani 1 1 d . . .
H5 H 1.3483 0.4788 0.0772 0.022 Uiso 1 1 calc R . .
C6 C 1.2150(8) 0.6822(5) 0.0440(2) 0.0192(9) Uani 1 1 d . . .
H6 H 1.3115 0.6936 0.0056 0.023 Uiso 1 1 calc R . .
C7 C 1.1254(8) 0.4019(5) 0.1933(2) 0.0207(9) Uani 1 1 d . . .
C8 C 0.5805(8) 1.1089(5) 0.3295(2) 0.0198(9) Uani 1 1 d . A .
C9 C 0.7714(10) 1.1691(6) 0.3815(2) 0.0302(11) Uani 1 1 d . . .
H9 H 0.9241 1.2402 0.3717 0.036 Uiso 1 1 calc R . .
C10 C 0.7404(9) 1.1258(6) 0.4481(2) 0.0282(11) Uani 1 1 d . . .
H10A H 0.8736 1.1671 0.4837 0.034 Uiso 1 1 calc R . .
C11 C 0.5180(8) 1.0229(5) 0.4641(2) 0.0188(9) Uani 1 1 d . . .
C12 C 0.3321(9) 0.9622(6) 0.4094(2) 0.0254(10) Uani 1 1 d . A .
H12A H 0.1800 0.8898 0.4187 0.030 Uiso 1 1 calc R . .
C13 C 0.3599(9) 1.0031(6) 0.3423(2) 0.0244(10) Uani 1 1 d . . .
C14 C 0.1549(11) 0.9354(9) 0.2839(3) 0.0474(17) Uani 1 1 d . A 1
H14A H 0.0143 0.8606 0.3019 0.071 Uiso 1 1 calc R A 1
H14B H 0.2329 0.8757 0.2503 0.071 Uiso 1 1 calc R A 1
H14C H 0.0851 1.0261 0.2618 0.071 Uiso 1 1 calc R A 1
C1S C 0.390(4) 1.393(2) 0.6512(5) 0.176(18) Uani 0.50 1 d PGU B -1
H1S1 H 0.3634 1.4747 0.6853 0.264 Uiso 0.50 1 calc PR B -1
H1S2 H 0.4787 1.3106 0.6740 0.264 Uiso 0.50 1 calc PR B -1
H1S3 H 0.2215 1.3394 0.6281 0.264 Uiso 0.50 1 calc PR B -1
C2S C 0.554(3) 1.4767(18) 0.5992(4) 0.278(19) Uani 0.50 1 d PGU B -1
H2S1 H 0.7166 1.4314 0.6011 0.334 Uiso 0.50 1 calc PR B -1
H2S2 H 0.6010 1.5950 0.6123 0.334 Uiso 0.50 1 calc PR B -1
C3S C 0.427(2) 1.4595(15) 0.5262(4) 0.184(14) Uani 0.50 1 d PGU B -1
H3S1 H 0.3852 1.3412 0.5128 0.220 Uiso 0.50 1 calc PR B -1
H3S2 H 0.2604 1.5007 0.5248 0.220 Uiso 0.50 1 calc PR B -1
C4S C 0.5801(17) 1.5456(12) 0.4745(4) 0.041(4) Uani 0.50 1 d PGU B -1
H4S1 H 0.7465 1.5044 0.4759 0.049 Uiso 0.50 1 calc PR B -1
H4S2 H 0.6217 1.6639 0.4880 0.049 Uiso 0.50 1 calc PR B -1
C5S C 0.4533(13) 1.5284(14) 0.4016(4) 0.036(3) Uani 0.50 1 d PGU B -1
H5S1 H 0.4060 1.4101 0.3884 0.043 Uiso 0.50 1 calc PR B -1
H5S2 H 0.2903 1.5737 0.3996 0.043 Uiso 0.50 1 calc PR B -1
C6S C 0.6169(14) 1.6120(11) 0.3495(3) 0.055(6) Uani 0.50 1 d PGU B -1
H6S1 H 0.5354 1.5703 0.3034 0.066 Uiso 0.50 1 calc PR B -1
H6S2 H 0.6107 1.7308 0.3525 0.066 Uiso 0.50 1 calc PR B -1
O1S O 0.8866(14) 1.5933(13) 0.3551(4) 0.080(4) Uani 0.50 1 d PGU B -1
H1S H 0.9257 1.5688 0.3163 0.121 Uiso 0.50 1 calc PR B -1
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
O1 Zn1 O1 180.0 . 2_775
O1 Zn1 N1 100.22(12) . 2_775
O1 Zn1 N1 79.78(12) 2_775 2_775
O1 Zn1 N1 79.78(12) . .
O1 Zn1 N1 100.22(12) 2_775 .
N1 Zn1 N1 179.998(1) 2_775 .
O1 Zn1 O3 88.59(12) . 2_775
O1 Zn1 O3 91.41(12) 2_775 2_775
N1 Zn1 O3 91.47(12) 2_775 2_775
N1 Zn1 O3 88.53(12) . 2_775
O1 Zn1 O3 91.41(12) . .
O1 Zn1 O3 88.59(12) 2_775 .
N1 Zn1 O3 88.53(12) 2_775 .
N1 Zn1 O3 91.47(12) . .
O3 Zn1 O3 180.0 2_775 .
C1 O1 Zn1 115.2(2) . .
Zn1 O3 H3A 122(4) . .
Zn1 O3 H3B 116(3) . .
H3A O3 H3B 99(5) . .
C6 N1 C2 118.1(4) . .
C6 N1 Zn1 129.8(3) . .
C2 N1 Zn1 112.1(3) . .
C8 N2 H2A 109.5 . .
C8 N2 H2B 109.5 . .
H2A N2 H2B 109.5 . .
C8 N2 H2C 109.5 . .
H2A N2 H2C 109.5 . .
H2B N2 H2C 109.5 . .
O2 C1 O1 124.7(4) . .
O2 C1 C2 119.1(4) . .
O1 C1 C2 116.2(3) . .
N1 C2 C3 123.0(4) . .
N1 C2 C1 116.7(4) . .
C3 C2 C1 120.4(4) . .
C2 C3 C4 119.1(4) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 117.5(4) . .
C5 C4 C7 122.5(4) . .
C3 C4 C7 120.0(4) . .
C6 C5 C4 119.9(4) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
N1 C6 C5 122.3(4) . .
N1 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
O4 C7 O5 125.6(4) . .
O4 C7 C4 117.7(4) . .
O5 C7 C4 116.7(4) . .
C9 C8 C13 121.2(4) . .
C9 C8 N2 120.5(4) . .
C13 C8 N2 118.2(4) . .
C8 C9 C10 119.8(4) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C9 C10 C11 121.4(4) . .
C9 C10 H10A 119.3 . .
C11 C10 H10A 119.3 . .
C10 C11 C12 116.7(4) . .
C10 C11 C11 121.7(5) . 2_676
C12 C11 C11 121.6(5) . 2_676
C13 C12 C11 122.9(4) . .
C13 C12 H12A 118.6 . .
C11 C12 H12A 118.6 . .
C8 C13 C12 118.0(4) . .
C8 C13 C14 120.3(4) . .
C12 C13 C14 121.7(4) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C1S C2S C3S 115.1 . .
C1S C2S H2S1 108.5 . .
C3S C2S H2S1 108.5 . .
C1S C2S H2S2 108.5 . .
C3S C2S H2S2 108.5 . .
H2S1 C2S H2S2 107.5 . .
C4S C3S C2S 116.2 . .
C4S C3S H3S1 108.2 . .
C2S C3S H3S1 108.2 . .
C4S C3S H3S2 108.2 . .
C2S C3S H3S2 108.2 . .
H3S1 C3S H3S2 107.4 . .
C3S C4S C5S 116.2 . .
C3S C4S H4S1 108.2 . .
C5S C4S H4S1 108.2 . .
C3S C4S H4S2 108.2 . .
C5S C4S H4S2 108.2 . .
H4S1 C4S H4S2 107.4 . .
C6S C5S C4S 115.1 . .
C6S C5S H5S1 108.5 . .
C4S C5S H5S1 108.5 . .
C6S C5S H5S2 108.5 . .
C4S C5S H5S2 108.5 . .
H5S1 C5S H5S2 107.5 . .
O1S C6S C5S 117.2 . .
O1S C6S H6S1 108.0 . .
C5S C6S H6S1 108.0 . .
O1S C6S H6S2 108.0 . .
C5S C6S H6S2 108.0 . .
H6S1 C6S H6S2 107.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.086(3) .
Zn1 O1 2.086(3) 2_775
Zn1 N1 2.102(4) 2_775
Zn1 N1 2.102(4) .
Zn1 O3 2.154(3) 2_775
Zn1 O3 2.154(3) .
O1 C1 1.283(5) .
O2 C1 1.229(5) .
O3 H3A 0.87(4) .
O3 H3B 0.88(4) .
O4 C7 1.238(5) .
O5 C7 1.263(5) .
N1 C6 1.343(5) .
N1 C2 1.344(5) .
N2 C8 1.462(5) .
N2 H2A 0.9100 .
N2 H2B 0.9100 .
N2 H2C 0.9100 .
C1 C2 1.516(6) .
C2 C3 1.368(6) .
C3 C4 1.404(6) .
C3 H3 0.9500 .
C4 C5 1.386(6) .
C4 C7 1.506(6) .
C5 C6 1.374(6) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C8 C9 1.375(7) .
C8 C13 1.377(6) .
C9 C10 1.380(6) .
C9 H9 0.9500 .
C10 C11 1.392(6) .
C10 H10A 0.9500 .
C11 C12 1.397(6) .
C11 C11 1.487(8) 2_676
C12 C13 1.383(6) .
C12 H12A 0.9500 .
C13 C14 1.515(7) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C1S C2S 1.5060 .
C1S H1S1 0.9800 .
C1S H1S2 0.9800 .
C1S H1S3 0.9800 .
C2S C3S 1.5084 .
C2S H2S1 0.9900 .
C2S H2S2 0.9900 .
C3S C4S 1.4791 .
C3S H3S1 0.9900 .
C3S H3S2 0.9900 .
C4S C5S 1.5084 .
C4S H4S1 0.9900 .
C4S H4S2 0.9900 .
C5S C6S 1.5060 .
C5S H5S1 0.9900 .
C5S H5S2 0.9900 .
C6S O1S 1.4452 .
C6S H6S1 0.9900 .
C6S H6S2 0.9900 .
O1S H1S 0.8400 .
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
O1 Zn1 O1 C1 112(4) 2_775 .
N1 Zn1 O1 C1 -179.9(3) 2_775 .
N1 Zn1 O1 C1 0.1(3) . .
O3 Zn1 O1 C1 88.9(3) 2_775 .
O3 Zn1 O1 C1 -91.1(3) . .
O1 Zn1 N1 C6 -178.3(4) . .
O1 Zn1 N1 C6 1.7(4) 2_775 .
N1 Zn1 N1 C6 -168(16) 2_775 .
O3 Zn1 N1 C6 92.8(4) 2_775 .
O3 Zn1 N1 C6 -87.2(4) . .
O1 Zn1 N1 C2 0.3(3) . .
O1 Zn1 N1 C2 -179.7(3) 2_775 .
N1 Zn1 N1 C2 10(16) 2_775 .
O3 Zn1 N1 C2 -88.6(3) 2_775 .
O3 Zn1 N1 C2 91.4(3) . .
Zn1 O1 C1 O2 178.2(3) . .
Zn1 O1 C1 C2 -0.5(5) . .
C6 N1 C2 C3 -0.4(6) . .
Zn1 N1 C2 C3 -179.2(3) . .
C6 N1 C2 C1 178.2(3) . .
Zn1 N1 C2 C1 -0.6(5) . .
O2 C1 C2 N1 -178.1(4) . .
O1 C1 C2 N1 0.7(6) . .
O2 C1 C2 C3 0.6(6) . .
O1 C1 C2 C3 179.4(4) . .
N1 C2 C3 C4 1.6(6) . .
C1 C2 C3 C4 -176.9(4) . .
C2 C3 C4 C5 -2.0(6) . .
C2 C3 C4 C7 176.5(4) . .
C3 C4 C5 C6 1.3(6) . .
C7 C4 C5 C6 -177.2(4) . .
C2 N1 C6 C5 -0.4(6) . .
Zn1 N1 C6 C5 178.2(3) . .
C4 C5 C6 N1 -0.1(6) . .
C5 C4 C7 O4 173.6(4) . .
C3 C4 C7 O4 -4.9(6) . .
C5 C4 C7 O5 -5.5(6) . .
C3 C4 C7 O5 176.0(4) . .
C13 C8 C9 C10 -1.3(8) . .
N2 C8 C9 C10 179.7(4) . .
C8 C9 C10 C11 -0.5(8) . .
C9 C10 C11 C12 1.8(8) . .
C9 C10 C11 C11 -179.3(5) . 2_676
C10 C11 C12 C13 -1.3(8) . .
C11 C11 C12 C13 179.7(5) 2_676 .
C9 C8 C13 C12 1.7(7) . .
N2 C8 C13 C12 -179.3(4) . .
C9 C8 C13 C14 -178.6(5) . .
N2 C8 C13 C14 0.4(7) . .
C11 C12 C13 C8 -0.3(8) . .
C11 C12 C13 C14 180.0(5) . .
C1S C2S C3S C4S 177.9 . .
C2S C3S C4S C5S 180.0 . .
C3S C4S C5S C6S -177.9 . .
C4S C5S C6S O1S 43.8 . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144620
