#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:19:41 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179660 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/13/4511356.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_4511356
loop_
_publ_author_name
'Imaz, Inhar'
'Thillet, Anthony'
'Sutter, Jean-Pascal'
_publ_section_title
;
 Charge-Assisted Hydrogen-Bonded Assemblage of an Anionic
 {M(C2O4)4}4-Building Unit and Organic Cations:  A Versatile
 Approach to Hybrid Supramolecular Architectures
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1753
_journal_paper_doi               10.1021/cg060905+
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C8 O16 Zr, 2(C10 H10 N2)'
_chemical_formula_sum            'C28 H20 N4 O16 Zr'
_chemical_formula_weight         759.70
_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                 121.24(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.451(1)
_cell_length_b                   10.994(1)
_cell_length_c                   15.087(1)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      1
_cell_volume                     2758.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10184
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   scalepack
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisme
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.358
_refine_diff_density_min         -1.575
_refine_diff_density_rms         0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0720
_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)+(0.1270P)²+35.5155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.2593
_reflns_number_gt                2425
_reflns_number_total             2733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060905%2Bsi20061211_093116.cif
_cod_data_source_block           Cmpd_1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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               4511356
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
Zr01 Zr 0.5000 0.20769(8) 0.7500 0.0275(4) Uani 1 2 d S
O7 O 0.0146(3) 0.1316(5) 0.3481(4) 0.0366(12) Uani 1 1 d .
O5 O 0.0775(4) -0.0500(5) 0.3872(5) 0.0491(15) Uani 1 1 d .
O6 O 0.2021(3) 0.0634(5) 0.3813(5) 0.0475(15) Uani 1 1 d .
O4 O 0.4468(4) 0.1479(5) 0.8400(5) 0.0431(14) Uani 1 1 d .
O8 O 0.1262(3) 0.2308(5) 0.3307(5) 0.0411(14) Uani 1 1 d .
O3 O 0.5677(3) 0.0505(5) 0.8467(5) 0.0404(13) Uani 1 1 d .
O2 O 0.5435(4) -0.1301(6) 0.8957(6) 0.0556(17) Uani 1 1 d .
N2 N 0.1069(5) 0.2418(6) 0.6039(6) 0.0410(16) Uani 1 1 d .
N1 N 0.2781(4) -0.3241(6) 0.6237(5) 0.0392(15) Uani 1 1 d .
C3 C 0.1781(4) 0.0219(7) 0.6212(6) 0.0307(15) Uani 1 1 d .
C14 C 0.4561(5) 0.0363(7) 0.8694(6) 0.0350(16) Uani 1 1 d .
C6 C 0.2141(4) -0.1006(7) 0.6254(6) 0.0330(15) Uani 1 1 d .
C1 C 0.0701(5) 0.1426(7) 0.6106(7) 0.0420(19) Uani 1 1 d .
H9 H 0.0220 0.1486 0.6095 0.050 Uiso 1 1 calc R
C2 C 0.1055(5) 0.0307(8) 0.6190(7) 0.0383(17) Uani 1 1 d .
C9 C 0.3195(5) -0.2217(8) 0.6332(7) 0.0441(19) Uani 1 1 d .
H7 H 0.3697 -0.2272 0.6400 0.053 Uiso 1 1 calc R
C11 C 0.0724(4) 0.0578(7) 0.3667(6) 0.0313(15) Uani 1 1 d .
C4 C 0.2125(5) 0.1277(7) 0.6150(7) 0.0375(17) Uani 1 1 d .
H5 H 0.2610 0.1248 0.6170 0.045 Uiso 1 1 calc R
C7 C 0.1744(5) -0.2088(8) 0.6179(8) 0.0429(19) Uani 1 1 d .
C13 C 0.5292(5) -0.0246(7) 0.8726(6) 0.0378(17) Uani 1 1 d .
C10 C 0.2885(4) -0.1099(7) 0.6331(7) 0.0383(17) Uani 1 1 d .
H6 H 0.3172 -0.0399 0.6381 0.046 Uiso 1 1 calc R
C12 C 0.1403(4) 0.1187(7) 0.3596(6) 0.0337(16) Uani 1 1 d .
C5 C 0.1761(5) 0.2387(8) 0.6060(7) 0.0438(19) Uani 1 1 d .
H20 H 0.1997 0.3102 0.6014 0.053 Uiso 1 1 calc R
C8 C 0.2070(5) -0.3174(8) 0.6172(7) 0.045(2) Uani 1 1 d .
H8 H 0.1794 -0.3886 0.6121 0.054 Uiso 1 1 calc R
O1 O 0.4138(3) -0.0196(5) 0.8926(5) 0.0413(13) Uani 1 1 d .
H1 H 0.297(5) -0.410(8) 0.615(6) 0.03(2) Uiso 1 1 d .
H2 H 0.086(5) 0.309(7) 0.594(6) 0.020(18) Uiso 1 1 d .
H4 H 0.132(5) -0.209(7) 0.610(6) 0.03(2) Uiso 1 1 d .
H3 H 0.083(6) -0.027(9) 0.620(7) 0.04(3) Uiso 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'
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'
Zr Zr -2.9673 0.5597 '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'
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
O4 Zr01 O4 145.1(3) 2_656 .
O4 Zr01 O3 70.6(2) 2_656 2_656
O4 Zr01 O3 82.1(2) . 2_656
O4 Zr01 O3 82.1(2) 2_656 .
O4 Zr01 O3 70.6(2) . .
O3 Zr01 O3 76.7(3) 2_656 .
O4 Zr01 O8 71.7(2) 2_656 8_556
O4 Zr01 O8 119.9(2) . 8_556
O3 Zr01 O8 135.9(2) 2_656 8_556
O3 Zr01 O8 76.3(2) . 8_556
O4 Zr01 O8 119.9(2) 2_656 7_556
O4 Zr01 O8 71.7(2) . 7_556
O3 Zr01 O8 76.3(2) 2_656 7_556
O3 Zr01 O8 135.9(2) . 7_556
O8 Zr01 O8 144.3(3) 8_556 7_556
O4 Zr01 O7 135.36(19) 2_656 8_556
O4 Zr01 O7 76.4(2) . 8_556
O3 Zr01 O7 152.69(19) 2_656 8_556
O3 Zr01 O7 110.8(2) . 8_556
O8 Zr01 O7 70.63(19) 8_556 8_556
O8 Zr01 O7 81.1(2) 7_556 8_556
O4 Zr01 O7 76.4(2) 2_656 7_556
O4 Zr01 O7 135.36(19) . 7_556
O3 Zr01 O7 110.8(2) 2_656 7_556
O3 Zr01 O7 152.69(19) . 7_556
O8 Zr01 O7 81.1(2) 8_556 7_556
O8 Zr01 O7 70.63(19) 7_556 7_556
O7 Zr01 O7 75.0(3) 8_556 7_556
C11 O7 Zr01 116.0(4) . 7_556
C14 O4 Zr01 118.2(5) . .
C12 O8 Zr01 117.4(5) . 7_556
C13 O3 Zr01 117.1(5) . .
C5 N2 C1 123.4(8) . .
C8 N1 C9 120.0(7) . .
C4 C3 C2 117.5(7) . .
C4 C3 C6 122.1(6) . .
C2 C3 C6 120.3(7) . .
O1 C14 O4 125.9(7) . .
O1 C14 C13 121.4(7) . .
O4 C14 C13 112.7(6) . .
C7 C6 C10 116.9(7) . .
C7 C6 C3 122.4(7) . .
C10 C6 C3 120.6(7) . .
N2 C1 C2 118.3(8) . .
C1 C2 C3 120.8(8) . .
N1 C9 C10 120.8(8) . .
O5 C11 O7 127.9(7) . .
O5 C11 C12 118.9(7) . .
O7 C11 C12 113.2(6) . .
C3 C4 C5 121.0(7) . .
C8 C7 C6 120.8(8) . .
O2 C13 O3 127.9(7) . .
O2 C13 C14 119.9(7) . .
O3 C13 C14 112.2(6) . .
C9 C10 C6 120.2(7) . .
O6 C12 O8 124.7(7) . .
O6 C12 C11 121.6(7) . .
O8 C12 C11 113.7(6) . .
N2 C5 C4 119.0(7) . .
N1 C8 C7 121.3(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr01 O4 2.191(5) 2_656
Zr01 O4 2.191(5) .
Zr01 O3 2.204(5) 2_656
Zr01 O3 2.204(5) .
Zr01 O8 2.206(5) 8_556
Zr01 O8 2.206(5) 7_556
Zr01 O7 2.226(5) 8_556
Zr01 O7 2.226(5) 7_556
O7 C11 1.295(9) .
O7 Zr01 2.226(5) 7_556
O5 C11 1.216(9) .
O6 C12 1.232(9) .
O4 C14 1.286(9) .
O8 C12 1.288(9) .
O8 Zr01 2.206(5) 7_556
O3 C13 1.305(10) .
O2 C13 1.201(10) .
N2 C5 1.332(11) .
N2 C1 1.336(11) .
N1 C8 1.336(11) .
N1 C9 1.348(11) .
C3 C4 1.368(10) .
C3 C2 1.400(11) .
C3 C6 1.504(10) .
C14 O1 1.215(9) .
C14 C13 1.548(10) .
C6 C7 1.391(11) .
C6 C10 1.394(11) .
C1 C2 1.382(12) .
C9 C10 1.369(12) .
C11 C12 1.533(10) .
C4 C5 1.381(12) .
C7 C8 1.354(12) .
