#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:50:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179542 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/11/4501156.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_4501156
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 H18 N2, C14 H10 N2 O10 Zn, C3 H6 O'
_chemical_formula_sum            'C31 H34 N4 O11 Zn'
_chemical_formula_weight         703.99
_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                90.174(7)
_cell_angle_beta                 95.130(7)
_cell_angle_gamma                100.135(7)
_cell_formula_units_Z            1
_cell_length_a                   5.1750(9)
_cell_length_b                   8.3571(13)
_cell_length_c                   19.712(4)
_cell_measurement_reflns_used    5586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.66
_cell_measurement_theta_min      3.20
_cell_volume                     835.7(3)
_computing_cell_refinement       'Bruker-Apex II (Bruker, 2006)'
_computing_data_collection       'Bruker-Apex II (Bruker, 2006)'
_computing_data_reduction        'Bruker-SAINT   (Bruker, 2006)'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15678
_diffrn_reflns_theta_full        23.88
_diffrn_reflns_theta_max         23.88
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.9103
_exptl_absorpt_correction_T_min  0.8193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.162
_refine_diff_density_min         -1.177
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0733
_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)+(0.1601P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2060
_reflns_number_gt                2128
_reflns_number_total             2528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200793f_si_002.cif
_cod_data_source_block           2d
_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_sg_symbol_H-M      P-1
_cod_database_code               4501156
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 0.0000 0.0000 0.0000 0.0196(4) Uani 1 2 d S . .
O1 O -0.2450(6) 0.0121(4) 0.07677(16) 0.0194(8) Uani 1 1 d . . .
O2 O -0.3745(6) -0.1090(4) 0.17164(17) 0.0228(8) Uani 1 1 d . . .
O3 O 0.3193(7) 0.1507(4) 0.0585(2) 0.0200(8) Uani 1 1 d . . .
H3A H 0.287(11) 0.192(7) 0.087(3) 0.022(19) Uiso 1 1 d . . .
H3B H 0.462(14) 0.105(9) 0.058(4) 0.06(2) Uiso 1 1 d . . .
O4 O -0.0232(8) -0.6042(4) 0.24277(18) 0.0340(10) Uani 1 1 d . . .
O5 O 0.2260(7) -0.7122(4) 0.17609(17) 0.0307(9) Uani 1 1 d . . .
N1 N 0.0600(7) -0.2078(4) 0.05543(19) 0.0176(9) Uani 1 1 d . . .
C1 C -0.0823(9) -0.2274(5) 0.1098(2) 0.0173(11) Uani 1 1 d . . .
C2 C -0.0774(9) -0.3559(6) 0.1533(2) 0.0187(11) Uani 1 1 d . . .
H2 H -0.1825 -0.3670 0.1908 0.022 Uiso 1 1 calc R . .
C3 C 0.0814(9) -0.4685(5) 0.1422(2) 0.0196(11) Uani 1 1 d . . .
C4 C 0.2281(9) -0.4495(6) 0.0859(2) 0.0200(11) Uani 1 1 d . . .
H4 H 0.3374 -0.5254 0.0764 0.024 Uiso 1 1 calc R . .
C5 C 0.2117(9) -0.3181(6) 0.0441(2) 0.0196(11) Uani 1 1 d . . .
H5 H 0.3121 -0.3055 0.0057 0.023 Uiso 1 1 calc R . .
C6 C -0.2482(9) -0.0984(6) 0.1213(3) 0.0203(11) Uani 1 1 d . . .
C7 C 0.0960(10) -0.6066(6) 0.1915(3) 0.0220(12) Uani 1 1 d . . .
N2 N -0.4269(9) 0.1447(5) 0.2569(2) 0.0273(10) Uani 1 1 d . . .
H2A H -0.4086 0.0555 0.2324 0.041 Uiso 1 1 calc R . .
H2B H -0.2836 0.2241 0.2539 0.041 Uiso 1 1 calc R . .
H2C H -0.5747 0.1814 0.2400 0.041 Uiso 1 1 calc R . .
C8 C -0.4490(10) 0.1013(6) 0.3286(2) 0.0244(12) Uani 1 1 d . A .
C9 C -0.6574(11) -0.0092(8) 0.3445(3) 0.0394(15) Uani 1 1 d D . .
C10 C -0.6735(11) -0.0468(8) 0.4132(3) 0.0411(16) Uani 1 1 d . A .
H10 H -0.8200 -0.1231 0.4254 0.049 Uiso 1 1 calc R . .
C11 C -0.4883(10) 0.0210(6) 0.4636(2) 0.0242(12) Uani 1 1 d . . .
C12 C -0.2773(15) 0.1298(9) 0.4444(3) 0.068(3) Uani 1 1 d . A .
H12 H -0.1431 0.1789 0.4779 0.082 Uiso 1 1 calc R . .
C13 C -0.2590(16) 0.1687(9) 0.3759(3) 0.067(3) Uani 1 1 d . . .
H13 H -0.1116 0.2431 0.3629 0.080 Uiso 1 1 calc R A .
C14 C -0.830(4) -0.121(3) 0.2898(8) 0.067(8) Uani 0.50 1 d PD A 1
H14A H -0.8945 -0.0546 0.2533 0.100 Uiso 0.50 1 calc PR A 1
H14B H -0.9799 -0.1845 0.3102 0.100 Uiso 0.50 1 calc PR A 1
H14C H -0.7252 -0.1943 0.2710 0.100 Uiso 0.50 1 calc PR A 1
C14' C -0.890(4) -0.048(2) 0.2911(10) 0.043(5) Uani 0.50 1 d PD A 2
H14D H -0.9002 0.0468 0.2627 0.064 Uiso 0.50 1 calc PR A 2
H14E H -1.0529 -0.0770 0.3136 0.064 Uiso 0.50 1 calc PR A 2
H14F H -0.8674 -0.1400 0.2625 0.064 Uiso 0.50 1 calc PR A 2
O1S O 0.196(4) 1.397(2) 0.5575(13) 0.185(9) Uani 0.50 1 d PU . .
C1S C 0.443(7) 1.452(3) 0.5862(13) 0.185(9) Uani 0.50 1 d PDU . .
C2S C 0.458(4) 1.415(3) 0.6610(12) 0.104(5) Uani 0.50 1 d PDU . .
H2S1 H 0.2849 1.4125 0.6777 0.156 Uiso 0.50 1 calc PR . .
H2S2 H 0.5873 1.5000 0.6859 0.156 Uiso 0.50 1 calc PR . .
H2S3 H 0.5127 1.3096 0.6679 0.156 Uiso 0.50 1 calc PR . .
C3S C 0.652(4) 1.539(3) 0.5422(11) 0.104(5) Uani 0.50 1 d PDU . .
H3S1 H 0.6091 1.4997 0.4949 0.156 Uiso 0.50 1 calc PR B -1
H3S2 H 0.8252 1.5152 0.5590 0.156 Uiso 0.50 1 calc PR B -1
H3S3 H 0.6555 1.6561 0.5444 0.156 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
O1 Zn1 N1 100.28(13) . 2
O1 Zn1 N1 79.72(13) 2 2
O1 Zn1 N1 79.72(13) . .
O1 Zn1 N1 100.28(13) 2 .
N1 Zn1 N1 180.0 2 .
O1 Zn1 O3 89.09(15) . 2
O1 Zn1 O3 90.91(15) 2 2
N1 Zn1 O3 92.17(13) 2 2
N1 Zn1 O3 87.83(13) . 2
O1 Zn1 O3 90.91(15) . .
O1 Zn1 O3 89.09(15) 2 .
N1 Zn1 O3 87.83(13) 2 .
N1 Zn1 O3 92.17(13) . .
O3 Zn1 O3 180.0 2 .
C6 O1 Zn1 115.9(3) . .
Zn1 O3 H3A 117(5) . .
Zn1 O3 H3B 108(4) . .
H3A O3 H3B 124(6) . .
C5 N1 C1 118.1(4) . .
C5 N1 Zn1 130.1(3) . .
C1 N1 Zn1 111.9(3) . .
N1 C1 C2 122.4(4) . .
N1 C1 C6 116.3(4) . .
C2 C1 C6 121.3(4) . .
C1 C2 C3 119.5(4) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C2 C3 C4 118.4(4) . .
C2 C3 C7 119.8(4) . .
C4 C3 C7 121.8(4) . .
C5 C4 C3 118.9(4) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
N1 C5 C4 122.7(4) . .
N1 C5 H5 118.6 . .
C4 C5 H5 118.6 . .
O2 C6 O1 125.5(4) . .
O2 C6 C1 118.3(4) . .
O1 C6 C1 116.1(4) . .
O4 C7 O5 126.3(4) . .
O4 C7 C3 116.6(4) . .
O5 C7 C3 117.1(4) . .
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 . .
C13 C8 C9 121.9(5) . .
C13 C8 N2 119.2(5) . .
C9 C8 N2 118.9(5) . .
C8 C9 C10 117.4(5) . .
C8 C9 C14' 117.3(10) . .
C10 C9 C14' 123.1(10) . .
C8 C9 C14 121.4(9) . .
C10 C9 C14 119.4(9) . .
C14' C9 C14 27.6(10) . .
C11 C10 C9 123.0(5) . .
C11 C10 H10 118.5 . .
C9 C10 H10 118.5 . .
C10 C11 C12 117.3(5) . .
C10 C11 C11 121.7(6) . 2_456
C12 C11 C11 121.1(6) . 2_456
C11 C12 C13 120.3(6) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C8 C13 C12 120.1(6) . .
C8 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
C9 C14' H14D 109.5 . .
C9 C14' H14E 109.5 . .
H14D C14' H14E 109.5 . .
C9 C14' H14F 109.5 . .
H14D C14' H14F 109.5 . .
H14E C14' H14F 109.5 . .
O1S C1S C2S 109(2) . .
O1S C1S C3S 120(2) . .
C2S C1S C3S 131(3) . .
C1S C2S H2S1 109.5 . .
C1S C2S H2S2 109.5 . .
H2S1 C2S H2S2 109.5 . .
C1S C2S H2S3 109.5 . .
H2S1 C2S H2S3 109.5 . .
H2S2 C2S H2S3 109.5 . .
C1S C3S H3S1 109.5 . .
C1S C3S H3S2 109.5 . .
C1S C3S H3S3 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 2.072(3) .
Zn1 O1 2.072(3) 2
Zn1 N1 2.109(4) 2
Zn1 N1 2.109(4) .
Zn1 O3 2.136(4) 2
Zn1 O3 2.136(4) .
O1 C6 1.275(6) .
O2 C6 1.232(6) .
O3 H3A 0.71(6) .
O3 H3B 0.89(8) .
O4 C7 1.232(6) .
O5 C7 1.252(6) .
N1 C5 1.342(6) .
N1 C1 1.347(6) .
C1 C2 1.380(7) .
C1 C6 1.520(7) .
C2 C3 1.383(7) .
C2 H2 0.9500 .
C3 C4 1.393(7) .
C3 C7 1.520(6) .
C4 C5 1.386(7) .
C4 H4 0.9500 .
C5 H5 0.9500 .
N2 C8 1.468(6) .
N2 H2A 0.9100 .
N2 H2B 0.9100 .
N2 H2C 0.9100 .
C8 C13 1.338(8) .
C8 C9 1.352(8) .
C9 C10 1.398(8) .
C9 C14' 1.516(14) .
C9 C14 1.535(13) .
C10 C11 1.363(8) .
C10 H10 0.9500 .
C11 C12 1.374(8) .
C11 C11 1.490(9) 2_456
C12 C13 1.398(8) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C14' H14D 0.9800 .
C14' H14E 0.9800 .
C14' H14F 0.9800 .
O1S C1S 1.35(3) .
C1S C2S 1.50(2) .
C1S C3S 1.53(2) .
C2S H2S1 0.9800 .
C2S H2S2 0.9800 .
C2S H2S3 0.9800 .
C3S H3S1 0.9800 .
C3S H3S2 0.9800 .
C3S H3S3 0.9800 .
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 C6 172(5) 2 .
N1 Zn1 O1 C6 -178.4(3) 2 .
N1 Zn1 O1 C6 1.6(3) . .
O3 Zn1 O1 C6 89.6(3) 2 .
O3 Zn1 O1 C6 -90.4(3) . .
O1 Zn1 N1 C5 179.4(4) . .
O1 Zn1 N1 C5 -0.6(4) 2 .
N1 Zn1 N1 C5 -134(5) 2 .
O3 Zn1 N1 C5 89.9(4) 2 .
O3 Zn1 N1 C5 -90.1(4) . .
O1 Zn1 N1 C1 0.0(3) . .
O1 Zn1 N1 C1 180.0(3) 2 .
N1 Zn1 N1 C1 46(5) 2 .
O3 Zn1 N1 C1 -89.5(3) 2 .
O3 Zn1 N1 C1 90.5(3) . .
C5 N1 C1 C2 -0.2(7) . .
Zn1 N1 C1 C2 179.3(3) . .
C5 N1 C1 C6 179.2(4) . .
Zn1 N1 C1 C6 -1.3(5) . .
N1 C1 C2 C3 1.0(7) . .
C6 C1 C2 C3 -178.3(4) . .
C1 C2 C3 C4 -1.3(7) . .
C1 C2 C3 C7 177.6(4) . .
C2 C3 C4 C5 0.8(7) . .
C7 C3 C4 C5 -178.1(4) . .
C1 N1 C5 C4 -0.3(7) . .
Zn1 N1 C5 C4 -179.7(3) . .
C3 C4 C5 N1 0.0(7) . .
Zn1 O1 C6 O2 177.7(4) . .
Zn1 O1 C6 C1 -2.8(5) . .
N1 C1 C6 O2 -177.7(4) . .
C2 C1 C6 O2 1.7(7) . .
N1 C1 C6 O1 2.8(6) . .
C2 C1 C6 O1 -177.8(4) . .
C2 C3 C7 O4 -5.1(7) . .
C4 C3 C7 O4 173.8(4) . .
C2 C3 C7 O5 174.4(4) . .
C4 C3 C7 O5 -6.7(7) . .
C13 C8 C9 C10 2.3(10) . .
N2 C8 C9 C10 -179.5(5) . .
C13 C8 C9 C14' 166.2(9) . .
N2 C8 C9 C14' -15.7(11) . .
C13 C8 C9 C14 -162.3(12) . .
N2 C8 C9 C14 15.8(14) . .
C8 C9 C10 C11 -0.9(10) . .
C14' C9 C10 C11 -163.7(9) . .
C14 C9 C10 C11 164.1(12) . .
C9 C10 C11 C12 -0.6(11) . .
C9 C10 C11 C11 179.7(7) . 2_456
C10 C11 C12 C13 0.6(12) . .
C11 C11 C12 C13 -179.6(8) 2_456 .
C9 C8 C13 C12 -2.3(12) . .
N2 C8 C13 C12 179.6(7) . .
C11 C12 C13 C8 0.8(14) . .
