#------------------------------------------------------------------------------
#$Date: 2019-11-23 10:26:00 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232868 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/83/4348305.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_4348305
loop_
_publ_author_name
'Haldar, Ritesh'
'Gurunatha, K. L.'
'Sikdar, Nivedita'
'Maji, Tapas Kumar'
_publ_section_title
;
 1D chains, 2D networks and 3D interdigitated frameworks of isoorotic acid
 or 4,4′-bipyridyl and isoorotic acid: syntheses, structures, and
 sorption properties
;
_journal_issue                   3
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              278
_journal_paper_doi               10.1039/C4QI00129J
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C20 H13 N5 Ni O5'
_chemical_formula_weight         462.06
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_cell_setting           monoclinic
_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_block_doi                 10.5517/cc139xkw
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-09-01 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9990(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3949(2)
_cell_length_b                   11.3275(2)
_cell_length_c                   18.6129(3)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.17
_cell_volume                     2135.47(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker,2000)'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16479
_diffrn_reflns_theta_full        25.70
_diffrn_reflns_theta_max         25.70
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.8059
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'Light green'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Square block'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0389
_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)+(0.0375P)²+1.2106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                3449
_reflns_number_total             4069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qi00129j2.cif
_cod_data_source_block           compound5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               4348305
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
Ni1 Ni 0.2500 0.28913(3) 0.7500 0.01878(12) Uani 1 2 d S
Ni2 Ni 0.7500 0.32594(3) 0.7500 0.01873(12) Uani 1 2 d S
N1 N 0.14726(19) 0.4139(2) 0.54091(11) 0.0340(5) Uani 1 1 d .
N2 N 0.3239(2) 0.4816(2) 0.49319(13) 0.0477(7) Uani 1 1 d .
N3 N 0.2500 0.4793(2) 0.7500 0.0304(7) Uani 1 2 d S
N4 N 0.2500 1.1035(2) 0.7500 0.0299(7) Uani 1 2 d S
N5 N 0.7500 0.5133(2) 0.7500 0.0283(7) Uani 1 2 d S
N6 N 0.7500 1.1410(2) 0.7500 0.0264(6) Uani 1 2 d S
O1 O 0.16508(16) 0.30042(14) 0.64125(9) 0.0263(4) Uani 1 1 d .
O2 O 0.43007(14) 0.28674(13) 0.72698(9) 0.0234(4) Uani 1 1 d .
O3 O 0.58274(15) 0.33074(14) 0.66603(9) 0.0255(4) Uani 1 1 d .
O4 O 0.64798(16) 0.31593(15) 0.83438(9) 0.0277(4) Uani 1 1 d .
O5 O 0.11177(19) 0.5352(2) 0.44261(12) 0.0572(6) Uani 1 1 d .
C1 C 0.4642(2) 0.32392(19) 0.66946(13) 0.0214(5) Uani 1 1 d .
C2 C 0.3624(2) 0.3657(2) 0.60610(13) 0.0265(5) Uani 1 1 d .
C3 C 0.2243(2) 0.3555(2) 0.60022(13) 0.0231(5) Uani 1 1 d .
C4 C 0.1932(3) 0.4801(3) 0.48998(15) 0.0386(7) Uani 1 1 d .
C5 C 0.4004(3) 0.4275(3) 0.54966(15) 0.0381(7) Uani 1 1 d .
H5 H 0.4906 0.4310 0.5521 0.046 Uiso 1 1 calc R
C6 C 0.1421(3) 0.5405(2) 0.71978(17) 0.0438(7) Uani 1 1 d .
H6 H 0.0660 0.4991 0.6981 0.053 Uiso 1 1 calc R
C7 C 0.1377(3) 0.6613(2) 0.7190(2) 0.0547(9) Uani 1 1 d .
H7 H 0.0594 0.6998 0.6977 0.066 Uiso 1 1 calc R
C8 C 0.2500 0.7268(3) 0.7500 0.0436(11) Uani 1 2 d S
C9 C 0.2500 0.8568(3) 0.7500 0.0482(11) Uani 1 2 d S
C10 C 0.3639(3) 0.9206(3) 0.7571(3) 0.0776(13) Uani 1 1 d .
H10 H 0.4446 0.8820 0.7633 0.093 Uiso 1 1 calc R
C11 C 0.3589(3) 1.0408(3) 0.7552(3) 0.0720(12) Uani 1 1 d .
H11 H 0.4375 1.0815 0.7577 0.086 Uiso 1 1 calc R
C12 C 0.7937(3) 0.5742(2) 0.81159(16) 0.0421(7) Uani 1 1 d .
H12 H 0.8234 0.5332 0.8554 0.051 Uiso 1 1 calc R
C13 C 0.7967(3) 0.6968(2) 0.81320(16) 0.0460(8) Uani 1 1 d .
H13 H 0.8305 0.7359 0.8573 0.055 Uiso 1 1 calc R
C14 C 0.7500 0.7602(3) 0.7500 0.0310(8) Uani 1 2 d S
C15 C 0.7500 0.8930(3) 0.7500 0.0310(8) Uani 1 2 d S
C16 C 0.7825(4) 0.9577(2) 0.81374(17) 0.0551(9) Uani 1 1 d .
H16 H 0.8053 0.9192 0.8589 0.066 Uiso 1 1 calc R
C17 C 0.7817(3) 1.0785(2) 0.81148(16) 0.0470(8) Uani 1 1 d .
H17 H 0.8048 1.1191 0.8559 0.056 Uiso 1 1 calc R
C18 C 0.0681(3) 0.9750(7) 0.5131(4) 0.142(3) Uani 1 1 d D
C19 C 0.0973(9) 0.8606(7) 0.4961(4) 0.148(3) Uani 1 1 d .
H19 H 0.0300 0.8106 0.4726 0.177 Uiso 1 1 calc R
C20 C 0.2293(10) 0.8193(6) 0.5143(4) 0.140(3) Uani 1 1 d .
H20 H 0.2499 0.7422 0.5040 0.168 Uiso 1 1 calc R
N7 N 0.3255(7) 0.8967(7) 0.5477(4) 0.154(2) Uani 1 1 d .
C21 C 0.2995(9) 1.0110(8) 0.5639(4) 0.150(3) Uani 1 1 d .
H21 H 0.3678 1.0616 0.5854 0.180 Uiso 1 1 calc R
C22 C 0.1686(9) 1.0505(7) 0.5474(4) 0.145(3) Uani 1 1 d .
H22 H 0.1490 1.1271 0.5594 0.174 Uiso 1 1 calc R
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_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4QI00129J 2015
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
O2 Ni1 O2 178.46(9) . 2_556
O2 Ni1 O1 90.30(6) . .
O2 Ni1 O1 89.80(6) 2_556 .
O2 Ni1 O1 89.80(6) . 2_556
O2 Ni1 O1 90.30(6) 2_556 2_556
O1 Ni1 O1 172.75(9) . 2_556
O2 Ni1 N4 89.23(4) . 1_545
O2 Ni1 N4 89.23(4) 2_556 1_545
O1 Ni1 N4 93.63(5) . 1_545
O1 Ni1 N4 93.63(5) 2_556 1_545
O2 Ni1 N3 90.77(4) . .
O2 Ni1 N3 90.77(4) 2_556 .
O1 Ni1 N3 86.37(5) . .
O1 Ni1 N3 86.37(5) 2_556 .
N4 Ni1 N3 180.000(1) 1_545 .
O3 Ni2 O3 176.98(9) . 2_656
O3 Ni2 O4 85.15(6) . 2_656
O3 Ni2 O4 95.01(6) 2_656 2_656
O3 Ni2 O4 95.01(6) . .
O3 Ni2 O4 85.15(6) 2_656 .
O4 Ni2 O4 173.77(9) 2_656 .
O3 Ni2 N6 91.51(5) . 1_545
O3 Ni2 N6 91.51(5) 2_656 1_545
O4 Ni2 N6 86.88(5) 2_656 1_545
O4 Ni2 N6 86.88(5) . 1_545
O3 Ni2 N5 88.49(5) . .
O3 Ni2 N5 88.49(5) 2_656 .
O4 Ni2 N5 93.12(5) 2_656 .
O4 Ni2 N5 93.12(5) . .
N6 Ni2 N5 180.000(1) 1_545 .
C4 N1 C3 125.8(2) . .
C5 N2 C4 116.8(2) . .
C6 N3 C6 117.3(3) 2_556 .
C6 N3 Ni1 121.36(16) 2_556 .
C6 N3 Ni1 121.36(16) . .
C11 N4 C11 115.0(3) 2_556 .
C11 N4 Ni1 122.50(17) 2_556 1_565
C11 N4 Ni1 122.50(17) . 1_565
C12 N5 C12 117.3(3) . 2_656
C12 N5 Ni2 121.34(16) . .
C12 N5 Ni2 121.34(16) 2_656 .
C17 N6 C17 115.3(3) 2_656 .
C17 N6 Ni2 122.36(16) 2_656 1_565
C17 N6 Ni2 122.36(16) . 1_565
C3 O1 Ni1 118.63(15) . .
C1 O2 Ni1 128.55(15) . .
C1 O3 Ni2 129.25(15) . .
O3 C1 O2 121.8(2) . .
O3 C1 C2 118.5(2) . .
O2 C1 C2 119.6(2) . .
C5 C2 C3 115.9(2) . .
C5 C2 C1 119.4(2) . .
C3 C2 C1 124.5(2) . .
O1 C3 N1 116.9(2) . .
O1 C3 C2 128.4(2) . .
N1 C3 C2 114.7(2) . .
O5 C4 N2 122.9(2) . .
O5 C4 N1 118.4(2) . .
N2 C4 N1 118.7(2) . .
N2 C5 C2 127.8(2) . .
N2 C5 H5 116.1 . .
C2 C5 H5 116.1 . .
N3 C6 C7 123.2(3) . .
N3 C6 H6 118.4 . .
C7 C6 H6 118.4 . .
C6 C7 C8 120.3(3) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C7 C8 C7 115.6(4) . 2_556
C7 C8 C9 122.18(18) . .
C7 C8 C9 122.18(18) 2_556 .
C10 C9 C10 116.2(4) . 2_556
C10 C9 C8 121.89(19) . .
C10 C9 C8 121.89(19) 2_556 .
C11 C10 C9 119.9(3) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
N4 C11 C10 124.4(3) . .
N4 C11 H11 117.8 . .
C10 C11 H11 117.8 . .
N5 C12 C13 122.7(3) . .
N5 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C14 C13 C12 120.2(3) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C13 116.8(3) 2_656 .
C13 C14 C15 121.60(17) 2_656 .
C13 C14 C15 121.60(17) . .
C16 C15 C16 115.4(3) . 2_656
C16 C15 C14 122.31(17) . .
C16 C15 C14 122.31(17) 2_656 .
C15 C16 C17 120.6(3) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
N6 C17 C16 124.1(3) . .
N6 C17 H17 118.0 . .
C16 C17 H17 118.0 . .
C19 C18 C22 120.0(5) . .
C19 C18 C18 121.3(9) . 3_576
C22 C18 C18 118.3(9) . 3_576
C18 C19 C20 120.3(7) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
N7 C20 C19 117.8(7) . .
N7 C20 H20 121.1 . .
C19 C20 H20 121.1 . .
C20 N7 C21 123.0(8) . .
N7 C21 C22 119.0(8) . .
N7 C21 H21 120.5 . .
C22 C21 H21 120.5 . .
C18 C22 C21 119.8(7) . .
C18 C22 H22 120.1 . .
C21 C22 H22 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O2 2.0122(15) .
Ni1 O2 2.0122(15) 2_556
Ni1 O1 2.0222(16) .
Ni1 O1 2.0222(16) 2_556
Ni1 N4 2.103(3) 1_545
Ni1 N3 2.155(3) .
Ni2 O3 2.0606(16) .
Ni2 O3 2.0606(16) 2_656
Ni2 O4 2.0865(15) 2_656
Ni2 O4 2.0865(15) .
Ni2 N6 2.095(3) 1_545
Ni2 N5 2.122(3) .
N1 C4 1.376(3) .
N1 C3 1.378(3) .
N2 C5 1.318(3) .
N2 C4 1.346(4) .
N3 C6 1.330(3) 2_556
N3 C6 1.330(3) .
N4 C11 1.321(3) 2_556
N4 C11 1.321(3) .
N4 Ni1 2.103(3) 1_565
N5 C12 1.328(3) .
N5 C12 1.328(3) 2_656
N6 C17 1.323(3) 2_656
N6 C17 1.323(3) .
N6 Ni2 2.095(3) 1_565
O1 C3 1.250(3) .
O2 C1 1.273(3) .
O3 C1 1.251(3) .
O5 C4 1.244(3) .
C1 C2 1.474(3) .
C2 C5 1.391(3) .
C2 C3 1.420(3) .
C5 H5 0.9300 .
C6 C7 1.369(4) .
C6 H6 0.9300 .
C7 C8 1.395(3) .
C7 H7 0.9300 .
C8 C7 1.395(3) 2_556
C8 C9 1.473(5) .
C9 C10 1.367(4) .
C9 C10 1.367(4) 2_556
C10 C11 1.363(4) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.389(4) .
C12 H12 0.9300 .
C13 C14 1.371(3) .
C13 H13 0.9300 .
C14 C13 1.371(3) 2_656
C14 C15 1.505(5) .
C15 C16 1.370(3) .
C15 C16 1.370(3) 2_656
C16 C17 1.369(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.384(9) .
C18 C22 1.391(9) .
C18 C18 1.5003(10) 3_576
C19 C20 1.416(10) .
C19 H19 0.9300 .
C20 N7 1.370(9) .
C20 H20 0.9300 .
N7 C21 1.369(9) .
C21 C22 1.399(9) .
C21 H21 0.9300 .
C22 H22 0.9300 .
