#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:54:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179546 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/15/4501573.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_4501573
loop_
_publ_author_name
'Hulvey, Zeric'
'Furman, Joshua D.'
'Turner, Sara A.'
'Tang, Min'
'Cheetham, Anthony K.'
_publ_section_title
;
 Dimensionality Trends in Metal−Organic Frameworks Containing
 Perfluorinated or Nonfluorinated Benzenedicarboxylates
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2041
_journal_paper_doi               10.1021/cg100121n
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C21 H22 N2 Ni O6'
_chemical_formula_weight         457.12
_chemical_name_common            Nickel-bipyridylpropane-terephthalate
_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                 113.853(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.771(2)
_cell_length_b                   15.488(2)
_cell_length_c                   16.598(2)
_cell_measurement_temperature    293(2)
_cell_volume                     3943.1(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Area Detector 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  0.0915
_diffrn_reflns_av_sigmaI/netI    0.0874
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15891
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0770
_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)+(0.0626P)²+6.5665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                2771
_reflns_number_total             3877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100121n_si_002.cif
_cod_data_source_block           compound_6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3943.0(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4501573
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
Ni1 Ni 0.72301(4) 0.18351(4) 0.17298(4) 0.0221(2) Uani 1 1 d .
C1 C 0.8567(3) 0.2786(3) 0.1227(3) 0.0232(11) Uani 1 1 d .
C2 C 0.9225(3) 0.5138(3) 0.1397(4) 0.0321(13) Uani 1 1 d .
H2 H 0.9010 0.5669 0.1480 0.039 Uiso 1 1 calc R
C3 C 0.9073(3) 0.3593(3) 0.1260(3) 0.0224(11) Uani 1 1 d .
C4 C 0.6967(3) 0.3349(3) 0.4200(3) 0.0267(12) Uani 1 1 d .
C5 C 0.8783(3) 0.4394(3) 0.1422(3) 0.0292(12) Uani 1 1 d .
H5 H 0.8292 0.4426 0.1548 0.035 Uiso 1 1 calc R
C6 C 0.6167(3) 0.4587(4) 0.4508(4) 0.0362(14) Uani 1 1 d .
H6A H 0.6214 0.4994 0.4969 0.043 Uiso 1 1 calc R
H6B H 0.6307 0.4893 0.4072 0.043 Uiso 1 1 calc R
C7 C 1.0267(3) 0.4325(3) 0.1099(3) 0.0299(12) Uani 1 1 d .
H7 H 1.0776 0.4294 0.1003 0.036 Uiso 1 1 calc R
C8 C 0.9979(3) 0.5114(3) 0.1252(3) 0.0206(11) Uani 1 1 d .
C9 C 0.6831(4) 0.3867(4) 0.4903(3) 0.0383(14) Uani 1 1 d .
H9A H 0.7382 0.4116 0.5296 0.046 Uiso 1 1 calc R
H9B H 0.6630 0.3488 0.5247 0.046 Uiso 1 1 calc R
C10 C 0.9813(3) 0.3578(3) 0.1084(3) 0.0298(12) Uani 1 1 d .
H10 H 1.0007 0.3055 0.0954 0.036 Uiso 1 1 calc R
C11 C 0.7612(4) 0.3549(4) 0.3933(4) 0.0481(17) Uani 1 1 d .
H11 H 0.8012 0.3981 0.4220 0.058 Uiso 1 1 calc R
C12 C 0.6517(4) 0.2300(3) 0.3059(4) 0.0374(14) Uani 1 1 d .
H12 H 0.6123 0.1868 0.2762 0.045 Uiso 1 1 calc R
C13 C 0.6426(4) 0.2692(4) 0.3760(4) 0.0393(14) Uani 1 1 d .
H13 H 0.5992 0.2508 0.3934 0.047 Uiso 1 1 calc R
C14 C 0.7674(4) 0.3113(4) 0.3237(4) 0.0445(15) Uani 1 1 d .
H14 H 0.8129 0.3259 0.3078 0.053 Uiso 1 1 calc R
C15 C 0.5257(4) 0.4274(4) 0.4088(4) 0.0472(16) Uani 1 1 d .
H15A H 0.5111 0.4018 0.4544 0.057 Uiso 1 1 calc R
H15B H 0.5237 0.3817 0.3682 0.057 Uiso 1 1 calc R
C16 C 1.0462(3) 0.5936(3) 0.1256(3) 0.0234(11) Uani 1 1 d .
C17 C 0.4553(4) 0.4920(3) 0.3593(4) 0.0335(13) Uani 1 1 d .
C18 C 0.4716(4) 0.5772(4) 0.3479(4) 0.0491(17) Uani 1 1 d .
H18 H 0.5283 0.5984 0.3731 0.059 Uiso 1 1 calc R
C19 C 0.3686(4) 0.4670(4) 0.3211(4) 0.0428(15) Uani 1 1 d .
H19 H 0.3533 0.4108 0.3285 0.051 Uiso 1 1 calc R
C20 C 0.4037(4) 0.6310(4) 0.2989(4) 0.0418(15) Uani 1 1 d .
H20 H 0.4164 0.6886 0.2931 0.050 Uiso 1 1 calc R
C21 C 0.3055(4) 0.5243(3) 0.2725(4) 0.0403(15) Uani 1 1 d .
H21 H 0.2481 0.5050 0.2469 0.048 Uiso 1 1 calc R
O1 O 0.8106(2) 0.2765(2) 0.1671(2) 0.0272(8) Uani 1 1 d .
O2 O 1.1283(2) 0.5892(2) 0.1608(2) 0.0293(8) Uani 1 1 d .
O3 O 1.0032(2) 0.6595(2) 0.0939(3) 0.0379(10) Uani 1 1 d .
O4 O 0.8625(2) 0.2174(2) 0.0751(2) 0.0329(9) Uani 1 1 d .
O5W O 0.7388(3) 0.1122(2) 0.0737(3) 0.0313(9) Uani 1 1 d .
O6W O 0.6272(2) 0.2622(2) 0.0859(3) 0.0308(9) Uani 1 1 d .
N1 N 0.3215(3) 0.6055(2) 0.2599(3) 0.0265(10) Uani 1 1 d .
N2 N 0.7129(3) 0.2497(3) 0.2781(3) 0.0257(10) Uani 1 1 d .
H5WA H 0.704(4) 0.103(3) 0.026(4) 0.031 Uiso 1 1 d .
H5WB H 0.778(4) 0.133(3) 0.067(4) 0.031 Uiso 1 1 d .
H6WA H 0.587(4) 0.244(4) 0.078(4) 0.031 Uiso 1 1 d .
H6WB H 0.623(3) 0.263(3) 0.027(4) 0.031 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'
Ni Ni 0.3393 1.1124 '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
O6W Ni1 N1 178.76(16) . 3_545
O6W Ni1 O5W 94.06(16) . .
N1 Ni1 O5W 85.50(16) 3_545 .
O6W Ni1 O1 85.60(14) . .
N1 Ni1 O1 93.24(15) 3_545 .
O5W Ni1 O1 90.68(14) . .
O6W Ni1 N2 89.52(16) . .
N1 Ni1 N2 90.93(16) 3_545 .
O5W Ni1 N2 176.41(16) . .
O1 Ni1 N2 89.80(14) . .
O6W Ni1 O2 89.90(14) . 3_445
N1 Ni1 O2 91.20(15) 3_545 3_445
O5W Ni1 O2 83.62(15) . 3_445
O1 Ni1 O2 172.48(13) . 3_445
N2 Ni1 O2 96.19(15) . 3_445
O4 C1 O1 124.4(5) . .
O4 C1 C3 117.6(4) . .
O1 C1 C3 118.0(4) . .
C5 C2 C8 121.6(5) . .
C5 C2 H2 119.2 . .
C8 C2 H2 119.2 . .
C10 C3 C5 117.8(4) . .
C10 C3 C1 121.3(4) . .
C5 C3 C1 120.8(4) . .
C11 C4 C13 116.1(5) . .
C11 C4 C9 121.3(5) . .
C13 C4 C9 122.5(5) . .
C2 C5 C3 120.2(5) . .
C2 C5 H5 119.9 . .
C3 C5 H5 119.9 . .
C15 C6 C9 113.4(5) . .
C15 C6 H6A 108.9 . .
C9 C6 H6A 108.9 . .
C15 C6 H6B 108.9 . .
C9 C6 H6B 108.9 . .
H6A C6 H6B 107.7 . .
C8 C7 C10 121.0(5) . .
C8 C7 H7 119.5 . .
C10 C7 H7 119.5 . .
C7 C8 C2 118.1(4) . .
C7 C8 C16 121.6(4) . .
C2 C8 C16 120.3(4) . .
C4 C9 C6 111.7(4) . .
C4 C9 H9A 109.3 . .
C6 C9 H9A 109.3 . .
C4 C9 H9B 109.3 . .
C6 C9 H9B 109.3 . .
H9A C9 H9B 107.9 . .
C7 C10 C3 121.2(5) . .
C7 C10 H10 119.4 . .
C3 C10 H10 119.4 . .
C4 C11 C14 120.0(5) . .
C4 C11 H11 120.0 . .
C14 C11 H11 120.0 . .
N2 C12 C13 124.2(5) . .
N2 C12 H12 117.9 . .
C13 C12 H12 117.9 . .
C4 C13 C12 120.4(5) . .
C4 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
N2 C14 C11 124.3(5) . .
N2 C14 H14 117.9 . .
C11 C14 H14 117.9 . .
C6 C15 C17 118.0(5) . .
C6 C15 H15A 107.8 . .
C17 C15 H15A 107.8 . .
C6 C15 H15B 107.8 . .
C17 C15 H15B 107.8 . .
H15A C15 H15B 107.1 . .
O3 C16 O2 125.4(5) . .
O3 C16 C8 118.4(4) . .
O2 C16 C8 116.2(4) . .
C18 C17 C19 115.8(5) . .
C18 C17 C15 123.7(5) . .
C19 C17 C15 120.5(5) . .
C17 C18 C20 119.9(5) . .
C17 C18 H18 120.1 . .
C20 C18 H18 120.1 . .
C21 C19 C17 120.5(5) . .
C21 C19 H19 119.7 . .
C17 C19 H19 119.7 . .
N1 C20 C18 123.8(5) . .
N1 C20 H20 118.1 . .
C18 C20 H20 118.1 . .
N1 C21 C19 123.5(5) . .
N1 C21 H21 118.2 . .
C19 C21 H21 118.2 . .
C1 O1 Ni1 130.6(3) . .
C16 O2 Ni1 130.4(3) . 3
Ni1 O5W H5WA 127(4) . .
Ni1 O5W H5WB 106(4) . .
H5WA O5W H5WB 105(6) . .
Ni1 O6W H6WA 108(5) . .
Ni1 O6W H6WB 117(3) . .
H6WA O6W H6WB 99(6) . .
C21 N1 C20 116.4(5) . .
C21 N1 Ni1 120.4(4) . 3_455
C20 N1 Ni1 122.9(3) . 3_455
C12 N2 C14 114.8(5) . .
C12 N2 Ni1 121.1(3) . .
C14 N2 Ni1 124.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O6W 2.068(4) .
Ni1 N1 2.083(4) 3_545
Ni1 O5W 2.087(4) .
Ni1 O1 2.088(3) .
Ni1 N2 2.089(4) .
Ni1 O2 2.107(3) 3_445
C1 O4 1.261(6) .
C1 O1 1.266(6) .
C1 C3 1.500(7) .
C2 C5 1.380(7) .
C2 C8 1.381(7) .
C2 H2 0.9300 .
C3 C10 1.385(7) .
C3 C5 1.398(7) .
C4 C11 1.362(7) .
C4 C13 1.362(7) .
C4 C9 1.507(7) .
C5 H5 0.9300 .
C6 C15 1.479(7) .
C6 C9 1.524(7) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.375(7) .
C7 C10 1.381(7) .
C7 H7 0.9300 .
C8 C16 1.506(6) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10 0.9300 .
C11 C14 1.378(8) .
C11 H11 0.9300 .
C12 N2 1.320(6) .
C12 C13 1.373(7) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 N2 1.326(6) .
C14 H14 0.9300 .
C15 C17 1.512(7) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 O3 1.238(6) .
C16 O2 1.261(6) .
C17 C18 1.376(7) .
C17 C19 1.386(8) .
C18 C20 1.380(8) .
C18 H18 0.9300 .
C19 C21 1.367(7) .
C19 H19 0.9300 .
C20 N1 1.325(7) .
C20 H20 0.9300 .
C21 N1 1.321(6) .
C21 H21 0.9300 .
O2 Ni1 2.107(3) 3
O5W H5WA 0.79(5) .
O5W H5WB 0.78(5) .
O6W H6WA 0.70(6) .
O6W H6WB 0.95(5) .
N1 Ni1 2.083(4) 3_455
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
O4 C1 C3 C10 -24.7(7) . .
O1 C1 C3 C10 155.8(5) . .
O4 C1 C3 C5 151.8(5) . .
O1 C1 C3 C5 -27.7(7) . .
C8 C2 C5 C3 -2.9(8) . .
C10 C3 C5 C2 0.6(8) . .
C1 C3 C5 C2 -176.0(5) . .
C10 C7 C8 C2 0.5(8) . .
C10 C7 C8 C16 -179.1(5) . .
C5 C2 C8 C7 2.3(8) . .
C5 C2 C8 C16 -178.1(5) . .
C11 C4 C9 C6 92.8(6) . .
C13 C4 C9 C6 -83.0(7) . .
C15 C6 C9 C4 74.0(6) . .
C8 C7 C10 C3 -2.8(8) . .
C5 C3 C10 C7 2.1(8) . .
C1 C3 C10 C7 178.7(5) . .
C13 C4 C11 C14 1.8(9) . .
C9 C4 C11 C14 -174.4(6) . .
C11 C4 C13 C12 -3.3(9) . .
C9 C4 C13 C12 172.8(5) . .
N2 C12 C13 C4 2.2(10) . .
C4 C11 C14 N2 1.1(10) . .
C9 C6 C15 C17 -173.9(5) . .
C7 C8 C16 O3 142.4(5) . .
C2 C8 C16 O3 -37.2(7) . .
C7 C8 C16 O2 -39.2(7) . .
C2 C8 C16 O2 141.2(5) . .
C6 C15 C17 C18 3.0(9) . .
C6 C15 C17 C19 -178.0(6) . .
C19 C17 C18 C20 -1.5(9) . .
C15 C17 C18 C20 177.6(6) . .
C18 C17 C19 C21 2.5(9) . .
C15 C17 C19 C21 -176.6(6) . .
C17 C18 C20 N1 -1.1(10) . .
C17 C19 C21 N1 -1.1(10) . .
O4 C1 O1 Ni1 -5.5(7) . .
C3 C1 O1 Ni1 174.0(3) . .
O6W Ni1 O1 C1 -98.6(4) . .
N1 Ni1 O1 C1 81.0(4) 3_545 .
O5W Ni1 O1 C1 -4.5(4) . .
N2 Ni1 O1 C1 171.9(4) . .
O2 Ni1 O1 C1 -45.1(12) 3_445 .
O3 C16 O2 Ni1 -4.4(8) . 3
C8 C16 O2 Ni1 177.3(3) . 3
C19 C21 N1 C20 -1.4(9) . .
C19 C21 N1 Ni1 172.9(5) . 3_455
C18 C20 N1 C21 2.5(9) . .
C18 C20 N1 Ni1 -171.6(5) . 3_455
C13 C12 N2 C14 0.6(9) . .
C13 C12 N2 Ni1 178.2(5) . .
C11 C14 N2 C12 -2.2(9) . .
C11 C14 N2 Ni1 -179.8(5) . .
O6W Ni1 N2 C12 82.7(4) . .
N1 Ni1 N2 C12 -98.5(4) 3_545 .
O5W Ni1 N2 C12 -94(3) . .
O1 Ni1 N2 C12 168.3(4) . .
O2 Ni1 N2 C12 -7.1(4) 3_445 .
O6W Ni1 N2 C14 -99.9(5) . .
N1 Ni1 N2 C14 78.9(5) 3_545 .
O5W Ni1 N2 C14 83(3) . .
O1 Ni1 N2 C14 -14.3(5) . .
O2 Ni1 N2 C14 170.2(4) 3_445 .
