#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237481.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237481
loop_
_publ_author_name
'Maercz, Matthias'
'Wragg, David Stephen'
'Dietzel, Pascal Daniel Croumbie'
'Fjellvåg, Helmer'
_publ_section_title
;
 Poly[bis(1,3-dimethyl-1,3-diazinan-2-one)(2,5-dioxidoterephthalato)zirconium(IV)]
;
_journal_coeditor_code           HB7026
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m153
_journal_paper_doi               10.1107/S1600536813003437
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Zr (C8 H2 O6) (C6 H12 N2 O)2]'
_chemical_formula_moiety         'C20 H26 N4 O8 Zr'
_chemical_formula_sum            'C20 H26 N4 O8 Zr'
_chemical_formula_weight         541.67
_chemical_name_systematic
Poly[bis(1,3-dimethyl-1,3-diazinan-2-one)(2,5-dioxidoterephthalato)zirconium(IV)]
_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                 102.2390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.761(2)
_cell_length_b                   8.4049(10)
_cell_length_c                   14.8816(17)
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      2.8
_cell_volume                     2293.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8477
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0377
_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)+(0.0462P)²+2.0694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2437
_reflns_number_total             2730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2237481
_cod_database_fobs_code          2237481
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.01168(12) 0.8750(3) 0.06523(15) 0.0370(5) Uani d . 1 1
C C2 -0.04708(11) 0.9809(3) 0.06010(16) 0.0389(5) Uani d . 1 1
C C3 -0.10053(13) 0.9651(4) 0.12208(19) 0.0494(6) Uani d . 1 1
C C4 0.05755(12) 0.8979(3) 0.00446(16) 0.0409(5) Uani d . 1 1
H H4 0.0968 0.8292 0.0072 0.049 Uiso calc R 1 1
C C5 0.13245(14) 0.4514(3) 0.28509(18) 0.0460(6) Uani d . 1 1
C C6 0.1951(3) 0.2463(6) 0.2172(4) 0.1152(19) Uani d . 1 1
H H6A 0.1811 0.1438 0.2380 0.138 Uiso calc R 1 1
H H6B 0.2043 0.2328 0.1559 0.138 Uiso calc R 1 1
C C7 0.2608(3) 0.3007(6) 0.2785(6) 0.137(3) Uani d . 1 1
H H7A 0.2813 0.3874 0.2491 0.164 Uiso calc R 1 1
H H7B 0.2961 0.2146 0.2880 0.164 Uiso calc R 1 1
C C8 0.25001(19) 0.3551(5) 0.3685(4) 0.0998(15) Uani d . 1 1
H H8A 0.2447 0.2635 0.4061 0.120 Uiso calc R 1 1
H H8B 0.2927 0.4139 0.3993 0.120 Uiso calc R 1 1
C C9 0.1770(2) 0.5490(5) 0.4385(2) 0.0860(12) Uani d . 1 1
H H9A 0.2201 0.5396 0.4862 0.129 Uiso calc R 1 1
H H9B 0.1357 0.5104 0.4607 0.129 Uiso calc R 1 1
H H9C 0.1694 0.6587 0.4211 0.129 Uiso calc R 1 1
C C10 0.0730(3) 0.3413(7) 0.1388(3) 0.1198(18) Uani d . 1 1
H H10A 0.0849 0.2712 0.0932 0.180 Uiso calc R 1 1
H H10B 0.0594 0.4435 0.1117 0.180 Uiso calc R 1 1
H H10C 0.0331 0.2977 0.1617 0.180 Uiso calc R 1 1
N N1 0.18563(12) 0.4566(3) 0.35990(19) 0.0583(6) Uani d . 1 1
N N2 0.13613(17) 0.3589(3) 0.2142(2) 0.0732(8) Uani d . 1 1
O O1 0.07673(10) 0.5374(2) 0.28218(12) 0.0532(5) Uani d . 1 1
O O2 -0.07967(9) 0.8873(2) 0.19808(13) 0.0519(5) Uani d . 1 1
O O3 0.02342(9) 0.7526(2) 0.12481(12) 0.0424(4) Uani d . 1 1
O O4 -0.16069(11) 1.0250(4) 0.10048(17) 0.0870(9) Uani d . 1 1
Zr Zr1 0.0000 0.72101(4) 0.2500 0.03776(12) Uani d S 1 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O3 C1 C4 . . 119.9(2)
O3 C1 C2 . . 122.5(2)
C4 C1 C2 . . 117.7(2)
C4 C2 C1 5_575 . 119.8(2)
C4 C2 C3 5_575 . 118.3(2)
C1 C2 C3 . . 121.8(2)
O4 C3 O2 . . 122.2(2)
O4 C3 C2 . . 120.2(2)
O2 C3 C2 . . 117.6(2)
C2 C4 C1 5_575 . 122.5(2)
C2 C4 H4 5_575 . 118.7
C1 C4 H4 . . 118.7
O1 C5 N2 . . 119.4(3)
O1 C5 N1 . . 118.6(2)
N2 C5 N1 . . 122.0(3)
C7 C6 N2 . . 110.9(4)
C7 C6 H6A . . 109.5
N2 C6 H6A . . 109.5
C7 C6 H6B . . 109.5
N2 C6 H6B . . 109.5
H6A C6 H6B . . 108.0
C6 C7 C8 . . 114.2(4)
C6 C7 H7A . . 108.7
C8 C7 H7A . . 108.7
C6 C7 H7B . . 108.7
C8 C7 H7B . . 108.7
H7A C7 H7B . . 107.6
N1 C8 C7 . . 111.9(4)
N1 C8 H8A . . 109.2
C7 C8 H8A . . 109.2
N1 C8 H8B . . 109.2
C7 C8 H8B . . 109.2
H8A C8 H8B . . 107.9
N1 C9 H9A . . 109.5
N1 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
N1 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
N2 C10 H10A . . 109.5
N2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
N2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C5 N1 C9 . . 120.3(2)
C5 N1 C8 . . 120.9(3)
C9 N1 C8 . . 118.4(3)
C5 N2 C6 . . 121.8(4)
C5 N2 C10 . . 120.2(3)
C6 N2 C10 . . 116.7(4)
C5 O1 Zr1 . . 162.17(19)
C3 O2 Zr1 . . 136.71(16)
C1 O3 Zr1 . . 132.13(15)
O3 Zr1 O3 . 2 164.90(10)
O3 Zr1 O2 . 2 88.54(7)
O3 Zr1 O2 2 2 81.27(7)
O3 Zr1 O2 . . 81.27(7)
O3 Zr1 O2 2 . 88.54(7)
O2 Zr1 O2 2 . 95.19(12)
O3 Zr1 O1 . 2 99.16(7)
O3 Zr1 O1 2 2 91.97(7)
O2 Zr1 O1 2 2 171.16(7)
O2 Zr1 O1 . 2 90.30(8)
O3 Zr1 O1 . . 91.97(7)
O3 Zr1 O1 2 . 99.16(7)
O2 Zr1 O1 2 . 90.30(8)
O2 Zr1 O1 . . 171.16(7)
O1 Zr1 O1 2 . 85.13(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O3 . 1.346(3) ?
C1 C4 . 1.388(3) ?
C1 C2 . 1.406(3) ?
C2 C4 5_575 1.386(3) ?
C2 C3 . 1.505(3) ?
C3 O4 . 1.215(3) ?
C3 O2 . 1.293(3) ?
C4 C2 5_575 1.386(3) ?
C4 H4 . 0.9300 ?
C5 O1 . 1.264(3) ?
C5 N2 . 1.325(4) ?
C5 N1 . 1.329(3) ?
C6 C7 . 1.443(8) ?
C6 N2 . 1.449(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.470(8) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.462(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N1 . 1.442(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 N2 . 1.456(5) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
Zr1 O1 . 2.0955(18) y
Zr2 O2 . 2.0723(18) y
Zr3 O3 . 2.0203(17) y
Zr1 O3 2 2.0203(17) ?
Zr1 O2 2 2.0723(18) ?
Zr1 O1 2 2.0955(18) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O3 C1 C2 C4 . 5_575 -178.2(2)
C4 C1 C2 C4 . 5_575 0.3(4)
O3 C1 C2 C3 . . 0.7(4)
C4 C1 C2 C3 . . 179.2(2)
C4 C2 C3 O4 5_575 . 20.1(4)
C1 C2 C3 O4 . . -158.8(3)
C4 C2 C3 O2 5_575 . -159.5(3)
C1 C2 C3 O2 . . 21.6(4)
O3 C1 C4 C2 . 5_575 178.2(2)
C2 C1 C4 C2 . 5_575 -0.3(4)
N2 C6 C7 C8 . . 47.7(6)
C6 C7 C8 N1 . . -44.6(6)
O1 C5 N1 C9 . . 4.8(4)
N2 C5 N1 C9 . . -175.0(3)
O1 C5 N1 C8 . . 177.6(3)
N2 C5 N1 C8 . . -2.2(5)
C7 C8 N1 C5 . . 21.3(5)
C7 C8 N1 C9 . . -165.7(4)
O1 C5 N2 C6 . . -173.7(3)
N1 C5 N2 C6 . . 6.0(5)
O1 C5 N2 C10 . . -7.7(5)
N1 C5 N2 C10 . . 172.1(4)
C7 C6 N2 C5 . . -28.8(6)
C7 C6 N2 C10 . . 164.6(5)
N2 C5 O1 Zr1 . . -75.3(7)
N1 C5 O1 Zr1 . . 104.9(6)
O4 C3 O2 Zr1 . . 160.2(3)
C2 C3 O2 Zr1 . . -20.1(4)
C4 C1 O3 Zr1 . . 152.68(18)
C2 C1 O3 Zr1 . . -28.8(3)
C1 O3 Zr1 O3 . 2 -23.03(19)
C1 O3 Zr1 O2 . 2 -70.4(2)
C1 O3 Zr1 O2 . . 25.1(2)
C1 O3 Zr1 O1 . 2 114.0(2)
C1 O3 Zr1 O1 . . -160.7(2)
C3 O2 Zr1 O3 . . 0.6(3)
C3 O2 Zr1 O3 . 2 169.4(3)
C3 O2 Zr1 O2 . 2 88.3(3)
C3 O2 Zr1 O1 . 2 -98.6(3)
C3 O2 Zr1 O1 . . -39.9(6)
C5 O1 Zr1 O3 . . 29.7(6)
C5 O1 Zr1 O3 . 2 -140.1(6)
C5 O1 Zr1 O2 . 2 -58.9(6)
C5 O1 Zr1 O2 . . 69.6(9)
C5 O1 Zr1 O1 . 2 128.7(6)
