#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/13/4511358.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_4511358
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         '2(C12 H12 N2), C8 O16 Zr, 4(H2O)'
_chemical_formula_sum            'C32 H32 N4 O20 Zr'
_chemical_formula_weight         883.84
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/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                 101.95(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.796(5)
_cell_length_b                   10.674(5)
_cell_length_c                   19.617(8)
_cell_measurement_temperature    180(2)
_cell_volume                     1801.9(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12736
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   scalepack
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisme
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0119(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0273
_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)+(0.0504P)²+0.5898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                3482
_reflns_number_total             3687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060905%2Bsi20061211_093116.cif
_cod_data_source_block           Cmpd_1c
_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_Hall     -P2yac
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               4511358
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
Zr1 Zr 0.7500 0.195952(19) 0.2500 0.01351(11) Uani 1 2 d S
O4 O 0.59440(14) 0.03275(12) 0.24768(6) 0.0202(3) Uani 1 1 d .
O1O O 0.2500 -0.0654(2) 0.2500 0.0372(5) Uani 1 2 d S
O2 O 0.55056(15) -0.13949(12) 0.30575(7) 0.0237(3) Uani 1 1 d .
O1 O 0.69937(16) -0.01969(13) 0.42650(7) 0.0253(3) Uani 1 1 d .
O3 O 0.76484(15) 0.12949(12) 0.35816(6) 0.0207(3) Uani 1 1 d .
O6 O 0.52468(14) 0.25716(12) 0.18973(6) 0.0220(3) Uani 1 1 d .
O5 O 0.67154(15) 0.35432(12) 0.30321(6) 0.0232(3) Uani 1 1 d .
C7 C 0.5457(2) 0.30419(17) 0.45079(11) 0.0247(4) Uani 1 1 d .
O7 O 0.5426(2) 0.53506(14) 0.28408(9) 0.0408(4) Uani 1 1 d .
O3O O 0.30510(17) 0.06258(15) 0.13379(8) 0.0292(3) Uani 1 1 d .
N1 N 0.48129(19) 0.21423(15) 0.55033(9) 0.0220(3) Uani 1 1 d .
O8 O 0.3562(2) 0.41531(16) 0.16772(8) 0.0434(4) Uani 1 1 d .
C13 C 0.9916(2) 0.75587(18) 0.49982(10) 0.0223(4) Uani 1 1 d .
C6 C 0.4660(2) 0.21728(18) 0.48069(10) 0.0248(4) Uani 1 1 d .
C1 C 0.69729(19) 0.02905(16) 0.36911(9) 0.0167(3) Uani 1 1 d .
C14 C 0.8754(2) 0.67923(18) 0.38577(10) 0.0240(4) Uani 1 1 d .
C5 C 0.5727(2) 0.29552(18) 0.59202(11) 0.0244(4) Uani 1 1 d .
C11 C 0.8175(2) 0.57306(17) 0.49246(9) 0.0203(4) Uani 1 1 d .
C10 C 0.7244(2) 0.48464(17) 0.45873(9) 0.0218(4) Uani 1 1 d .
C16 C 1.0614(2) 0.84934(18) 0.46909(10) 0.0241(4) Uani 1 1 d .
C8 C 0.6550(2) 0.38464(18) 0.56455(10) 0.0230(4) Uani 1 1 d .
N2 N 1.03766(18) 0.85700(15) 0.39961(9) 0.0240(3) Uani 1 1 d .
C2 C 0.60533(18) -0.03430(16) 0.30245(9) 0.0166(3) Uani 1 1 d .
C4 C 0.4706(2) 0.36491(17) 0.20222(9) 0.0237(4) Uani 1 1 d .
C12 C 0.8949(2) 0.66898(17) 0.45831(9) 0.0187(3) Uani 1 1 d .
C9 C 0.6427(2) 0.39101(17) 0.49245(9) 0.0198(4) Uani 1 1 d .
C15 C 0.9485(2) 0.77437(19) 0.35769(10) 0.0258(4) Uani 1 1 d .
C3 C 0.5668(2) 0.42751(18) 0.26841(9) 0.0241(4) Uani 1 1 d .
O2O O 0.2500 -0.3376(2) 0.2500 0.0352(5) Uani 1 2 d S
H13 H 1.008(2) 0.754(2) 0.5468(13) 0.022(5) Uiso 1 1 d .
H14 H 0.809(3) 0.622(2) 0.3526(13) 0.029(6) Uiso 1 1 d .
H6 H 0.401(3) 0.154(2) 0.4563(13) 0.028(6) Uiso 1 1 d .
H16 H 1.128(2) 0.913(2) 0.4954(12) 0.024(5) Uiso 1 1 d .
H15 H 0.940(3) 0.782(2) 0.3111(15) 0.036(7) Uiso 1 1 d .
H11 H 0.838(3) 0.581(2) 0.5449(13) 0.031(6) Uiso 1 1 d .
H1 H 0.426(3) 0.153(3) 0.5685(14) 0.037(7) Uiso 1 1 d .
H7 H 0.532(3) 0.303(2) 0.4019(15) 0.038(7) Uiso 1 1 d .
H5 H 0.574(3) 0.291(2) 0.6385(15) 0.034(7) Uiso 1 1 d .
H10 H 0.707(3) 0.474(3) 0.4076(15) 0.042(7) Uiso 1 1 d .
H8 H 0.721(3) 0.437(2) 0.5966(14) 0.037(6) Uiso 1 1 d .
H2 H 1.083(3) 0.919(3) 0.3828(15) 0.043(7) Uiso 1 1 d .
H2O H 0.175(3) -0.380(3) 0.2502(17) 0.056(9) Uiso 1 1 d .
H3O H 0.270(4) 0.029(3) 0.166(2) 0.075(12) Uiso 1 1 d .
H1O H 0.174(3) -0.110(3) 0.2419(15) 0.043(8) Uiso 1 1 d .
H4O H 0.366(3) 0.128(3) 0.1484(16) 0.055(9) 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'
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'
Zr Zr -2.9673 0.5597 '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
O5 Zr1 O5 77.86(7) 2_655 .
O5 Zr1 O6 71.65(5) 2_655 2_655
O5 Zr1 O6 81.41(5) . 2_655
O5 Zr1 O6 81.37(5) 2_655 .
O5 Zr1 O6 71.61(5) . .
O6 Zr1 O6 145.23(7) 2_655 .
O5 Zr1 O4 149.34(5) 2_655 .
O5 Zr1 O4 111.47(5) . .
O6 Zr1 O4 137.27(5) 2_655 .
O6 Zr1 O4 74.72(5) . .
O5 Zr1 O4 111.48(5) 2_655 2_655
O5 Zr1 O4 149.36(5) . 2_655
O6 Zr1 O4 74.70(5) 2_655 2_655
O6 Zr1 O4 137.29(5) . 2_655
O4 Zr1 O4 75.96(7) . 2_655
O5 Zr1 O3 138.38(5) 2_655 .
O5 Zr1 O3 75.56(5) . .
O6 Zr1 O3 73.17(5) 2_655 .
O6 Zr1 O3 118.72(5) . .
O4 Zr1 O3 71.39(4) . .
O4 Zr1 O3 79.32(5) 2_655 .
O5 Zr1 O3 75.56(5) 2_655 2_655
O5 Zr1 O3 138.39(5) . 2_655
O6 Zr1 O3 118.72(5) 2_655 2_655
O6 Zr1 O3 73.21(5) . 2_655
O4 Zr1 O3 79.30(5) . 2_655
O4 Zr1 O3 71.36(4) 2_655 2_655
O3 Zr1 O3 142.64(6) . 2_655
C2 O4 Zr1 119.05(10) . .
C1 O3 Zr1 119.82(11) . .
C4 O6 Zr1 119.58(11) . .
C3 O5 Zr1 118.70(11) . .
C6 C7 C9 120.20(18) . .
C5 N1 C6 121.70(17) . .
C16 C13 C12 119.88(18) . .
N1 C6 C7 120.03(17) . .
O1 C1 O3 126.29(16) . .
O1 C1 C2 119.56(15) . .
O3 C1 C2 114.15(14) . .
C15 C14 C12 119.65(17) . .
N1 C5 C8 120.52(19) . .
C10 C11 C12 124.30(17) . .
C11 C10 C9 124.54(17) . .
N2 C16 C13 120.11(17) . .
C5 C8 C9 119.68(17) . .
C16 N2 C15 122.16(17) . .
O2 C2 O4 126.43(16) . .
O2 C2 C1 119.86(15) . .
O4 C2 C1 113.70(14) . .
O8 C4 O6 125.84(18) . .
O8 C4 C3 121.47(17) . .
O6 C4 C3 112.69(15) . .
C13 C12 C14 118.09(17) . .
C13 C12 C11 118.70(17) . .
C14 C12 C11 123.21(16) . .
C8 C9 C7 117.88(17) . .
C8 C9 C10 123.20(16) . .
C7 C9 C10 118.91(17) . .
N2 C15 C14 120.08(18) . .
O7 C3 O5 125.47(18) . .
O7 C3 C4 121.64(17) . .
O5 C3 C4 112.89(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr1 O5 2.1722(13) 2_655
Zr1 O5 2.1736(13) .
Zr1 O6 2.1865(12) 2_655
Zr1 O6 2.1872(12) .
Zr1 O4 2.2092(12) .
Zr1 O4 2.2108(12) 2_655
Zr1 O3 2.2151(12) .
Zr1 O3 2.2155(12) 2_655
O4 C2 1.278(2) .
O2 C2 1.228(2) .
O1 C1 1.237(2) .
O3 C1 1.265(2) .
O6 C4 1.288(2) .
O5 C3 1.290(2) .
C7 C6 1.365(3) .
C7 C9 1.402(3) .
O7 C3 1.219(2) .
N1 C5 1.340(3) .
N1 C6 1.345(3) .
O8 C4 1.216(2) .
C13 C16 1.374(3) .
C13 C12 1.400(3) .
C1 C2 1.544(2) .
C14 C15 1.376(3) .
C14 C12 1.402(3) .
C5 C8 1.371(3) .
C11 C10 1.332(3) .
C11 C12 1.465(2) .
C10 C9 1.465(2) .
C16 N2 1.338(3) .
C8 C9 1.398(2) .
N2 C15 1.342(3) .
C4 C3 1.547(3) .
