#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/15/4501572.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_4501572
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 H20 N2 Ni O5'
_chemical_formula_weight         439.09
_chemical_name_common            Nickel-bipyridylpropane-isophthalate
_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                81.037(3)
_cell_angle_beta                 71.100(3)
_cell_angle_gamma                65.366(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4552(17)
_cell_length_b                   10.0780(18)
_cell_length_c                   11.923(2)
_cell_measurement_temperature    293(2)
_cell_volume                     976.8(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6167
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .11
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0411
_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)+(0.0376P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                2025
_reflns_number_total             2824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100121n_si_002.cif
_cod_data_source_block           compound_5
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C21 H20 N2 Ni1 O5'
_cod_database_code               4501572
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
O3 O 0.2465(3) -0.4179(3) 0.2669(2) 0.0404(7) Uani 1 1 d .
C21 C 0.2940(4) -0.3161(4) 0.2195(3) 0.0294(9) Uani 1 1 d .
N2 N -0.4018(3) 0.3142(3) 1.1788(3) 0.0318(8) Uani 1 1 d .
C12 C -0.3158(4) 0.2149(4) 1.0943(3) 0.0353(10) Uani 1 1 d .
H12 H -0.3679 0.1650 1.0749 0.042 Uiso 1 1 calc R
C13 C -0.3220(5) 0.3779(4) 1.2084(3) 0.0365(10) Uani 1 1 d .
H13 H -0.3781 0.4447 1.2691 0.044 Uiso 1 1 calc R
C10 C -0.1598(4) 0.3501(4) 1.1538(3) 0.0357(10) Uani 1 1 d .
H10 H -0.1092 0.3976 1.1781 0.043 Uiso 1 1 calc R
C11 C -0.1550(4) 0.1822(4) 1.0345(4) 0.0381(11) Uani 1 1 d .
H11 H -0.1014 0.1137 0.9750 0.046 Uiso 1 1 calc R
C9 C -0.0731(4) 0.2521(4) 1.0634(3) 0.0310(9) Uani 1 1 d .
Ni1 Ni 0.35158(6) 0.36658(5) 0.24038(4) 0.02979(19) Uani 1 1 d .
N1 N 0.3486(3) 0.3303(3) 0.4169(3) 0.0298(8) Uani 1 1 d .
C1 C 0.2035(5) 0.3913(4) 0.6191(4) 0.0402(11) Uani 1 1 d .
H1 H 0.1141 0.4558 0.6725 0.048 Uiso 1 1 calc R
C2 C 0.2259(4) 0.4168(4) 0.4997(3) 0.0351(10) Uani 1 1 d .
H2 H 0.1501 0.5003 0.4749 0.042 Uiso 1 1 calc R
C3 C 0.3143(4) 0.2691(4) 0.6605(4) 0.0322(10) Uani 1 1 d .
C4 C 0.4430(5) 0.1800(4) 0.5746(4) 0.0462(12) Uani 1 1 d .
H4 H 0.5220 0.0971 0.5968 0.055 Uiso 1 1 calc R
C5 C 0.4549(5) 0.2132(4) 0.4563(4) 0.0452(12) Uani 1 1 d .
H5 H 0.5424 0.1501 0.4008 0.054 Uiso 1 1 calc R
C6 C 0.2948(4) 0.2345(4) 0.7905(3) 0.0383(11) Uani 1 1 d .
H6A H 0.3340 0.2927 0.8205 0.046 Uiso 1 1 calc R
H6B H 0.3622 0.1325 0.8005 0.046 Uiso 1 1 calc R
C7 C 0.1206(4) 0.2629(5) 0.8642(3) 0.0474(12) Uani 1 1 d .
H7A H 0.0806 0.2062 0.8333 0.057 Uiso 1 1 calc R
H7B H 0.0535 0.3653 0.8557 0.057 Uiso 1 1 calc R
C8 C 0.1023(4) 0.2246(4) 0.9958(3) 0.0392(11) Uani 1 1 d .
H8A H 0.1701 0.1227 1.0052 0.047 Uiso 1 1 calc R
H8B H 0.1387 0.2832 1.0281 0.047 Uiso 1 1 calc R
C14 C 0.1502(4) 0.0818(4) 0.2875(3) 0.0245(9) Uani 1 1 d .
C15 C 0.2210(4) 0.1944(4) 0.2653(3) 0.0283(9) Uani 1 1 d .
C16 C -0.0090(4) 0.1121(4) 0.3558(3) 0.0329(10) Uani 1 1 d .
H16 H -0.0754 0.2056 0.3842 0.039 Uiso 1 1 calc R
C17 C 0.2450(4) -0.0575(4) 0.2433(3) 0.0275(9) Uani 1 1 d .
H17 H 0.3506 -0.0776 0.1951 0.033 Uiso 1 1 calc R
C18 C -0.0694(4) 0.0044(4) 0.3819(3) 0.0351(10) Uani 1 1 d .
H18 H -0.1763 0.0257 0.4280 0.042 Uiso 1 1 calc R
C19 C 0.1865(4) -0.1676(4) 0.2690(3) 0.0261(9) Uani 1 1 d .
C20 C 0.0273(4) -0.1350(4) 0.3401(3) 0.0330(10) Uani 1 1 d .
H20 H -0.0141 -0.2073 0.3596 0.040 Uiso 1 1 calc R
O1 O 0.3748(3) 0.1545(2) 0.2261(2) 0.0353(7) Uani 1 1 d .
O2 O 0.1305(3) 0.3258(3) 0.2878(2) 0.0346(7) Uani 1 1 d .
O4 O 0.4202(3) -0.3321(3) 0.1386(3) 0.0530(9) Uani 1 1 d .
O5 O 0.3318(4) 0.4205(3) 0.0648(3) 0.0468(9) Uani 1 1 d .
H100 H 0.404(5) 0.378(5) 0.007(4) 0.056 Uiso 1 1 d .
H101 H 0.310(6) 0.493(5) 0.054(4) 0.056 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
C21 O3 Ni1 131.1(2) . 1_545
O4 C21 O3 124.9(3) . .
O4 C21 C19 119.4(3) . .
O3 C21 C19 115.7(3) . .
C13 N2 C12 116.6(3) . .
C13 N2 Ni1 126.0(3) . 1_456
C12 N2 Ni1 117.2(3) . 1_456
N2 C12 C11 123.7(4) . .
N2 C12 H12 118.1 . .
C11 C12 H12 118.1 . .
N2 C13 C10 123.4(4) . .
N2 C13 H13 118.3 . .
C10 C13 H13 118.3 . .
C9 C10 C13 119.9(4) . .
C9 C10 H10 120.1 . .
C13 C10 H10 120.1 . .
C12 C11 C9 119.5(4) . .
C12 C11 H11 120.3 . .
C9 C11 H11 120.3 . .
C10 C9 C11 116.9(3) . .
C10 C9 C8 121.9(3) . .
C11 C9 C8 121.2(3) . .
O3 Ni1 N2 106.41(11) 1_565 1_654
O3 Ni1 N1 89.47(11) 1_565 .
N2 Ni1 N1 94.05(12) 1_654 .
O3 Ni1 O1 159.65(10) 1_565 .
N2 Ni1 O1 93.77(11) 1_654 .
N1 Ni1 O1 91.74(11) . .
O3 Ni1 O5 86.19(11) 1_565 .
N2 Ni1 O5 90.57(13) 1_654 .
N1 Ni1 O5 174.40(11) . .
O1 Ni1 O5 91.11(11) . .
O3 Ni1 O2 97.69(10) 1_565 .
N2 Ni1 O2 155.78(11) 1_654 .
N1 Ni1 O2 88.40(10) . .
O1 Ni1 O2 62.05(9) . .
O5 Ni1 O2 88.68(12) . .
O3 Ni1 C15 128.44(12) 1_565 .
N2 Ni1 C15 125.10(12) 1_654 .
N1 Ni1 C15 89.18(12) . .
O1 Ni1 C15 31.33(10) . .
O5 Ni1 C15 90.75(12) . .
O2 Ni1 C15 30.74(9) . .
C2 N1 C5 115.8(3) . .
C2 N1 Ni1 120.3(3) . .
C5 N1 Ni1 123.5(3) . .
C2 C1 C3 120.0(3) . .
C2 C1 H1 120.0 . .
C3 C1 H1 120.0 . .
N1 C2 C1 124.3(3) . .
N1 C2 H2 117.8 . .
C1 C2 H2 117.8 . .
C4 C3 C1 115.8(4) . .
C4 C3 C6 121.9(3) . .
C1 C3 C6 122.3(3) . .
C5 C4 C3 120.3(4) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
N1 C5 C4 123.8(3) . .
N1 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
C3 C6 C7 113.8(3) . .
C3 C6 H6A 108.8 . .
C7 C6 H6A 108.8 . .
C3 C6 H6B 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 113.5(3) . .
C6 C7 H7A 108.9 . .
C8 C7 H7A 108.9 . .
C6 C7 H7B 108.9 . .
C8 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C9 C8 C7 110.8(3) . .
C9 C8 H8A 109.5 . .
C7 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C16 C14 C17 118.6(3) . .
C16 C14 C15 121.0(3) . .
C17 C14 C15 120.3(3) . .
O2 C15 O1 120.6(3) . .
O2 C15 C14 120.3(3) . .
O1 C15 C14 119.0(3) . .
O2 C15 Ni1 62.43(19) . .
O1 C15 Ni1 58.22(17) . .
C14 C15 Ni1 175.0(3) . .
C18 C16 C14 120.4(3) . .
C18 C16 H16 119.8 . .
C14 C16 H16 119.8 . .
C14 C17 C19 121.9(3) . .
C14 C17 H17 119.1 . .
C19 C17 H17 119.1 . .
C16 C18 C20 120.6(3) . .
C16 C18 H18 119.7 . .
C20 C18 H18 119.7 . .
C17 C19 C20 118.3(3) . .
C17 C19 C21 119.7(3) . .
C20 C19 C21 122.1(3) . .
C18 C20 C19 120.3(3) . .
C18 C20 H20 119.8 . .
C19 C20 H20 119.8 . .
C15 O1 Ni1 90.5(2) . .
C15 O2 Ni1 86.8(2) . .
Ni1 O5 H100 122(3) . .
Ni1 O5 H101 110(4) . .
H100 O5 H101 108(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C21 1.270(4) .
O3 Ni1 2.004(2) 1_545
C21 O4 1.233(4) .
C21 C19 1.497(5) .
N2 C13 1.324(4) .
N2 C12 1.335(4) .
N2 Ni1 2.059(3) 1_456
C12 C11 1.373(5) .
C12 H12 0.9300 .
C13 C10 1.381(5) .
C13 H13 0.9300 .
C10 C9 1.376(5) .
C10 H10 0.9300 .
C11 C9 1.385(5) .
C11 H11 0.9300 .
C9 C8 1.516(5) .
Ni1 O3 2.004(2) 1_565
Ni1 N2 2.059(3) 1_654
Ni1 N1 2.072(3) .
Ni1 O1 2.084(2) .
Ni1 O5 2.128(3) .
Ni1 O2 2.176(2) .
Ni1 C15 2.451(4) .
N1 C2 1.328(4) .
N1 C5 1.330(5) .
C1 C2 1.369(5) .
C1 C3 1.388(5) .
C1 H1 0.9300 .
C2 H2 0.9300 .
C3 C4 1.379(5) .
C3 C6 1.503(5) .
C4 C5 1.377(5) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.522(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.527(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C14 C16 1.387(5) .
C14 C17 1.389(4) .
C14 C15 1.494(5) .
C15 O2 1.255(4) .
C15 O1 1.275(4) .
C16 C18 1.377(5) .
C16 H16 0.9300 .
C17 C19 1.389(5) .
C17 H17 0.9300 .
C18 C20 1.382(5) .
C18 H18 0.9300 .
C19 C20 1.393(5) .
C20 H20 0.9300 .
O5 H100 0.82(4) .
O5 H101 0.68(4) .
