#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:39:22 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180348 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/17/7201746.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_7201746
loop_
_publ_author_name
'Zhong, Rui-Qin'
'Zou, Ru-Qiang'
'Du, Miao'
'Jiang, Ling'
'Yamada, Tetsuya'
'Maruta, Goro'
'Takeda, Sadamu'
'Xu, Qiang'
_publ_section_title
;
 Metal--organic coordination architectures with
 3-pyridin-3-yl-benzoate: crystal structures, fluorescent emission and
 magnetic properties
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              605
_journal_paper_doi               10.1039/b714491a
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C24 H18 N2 Ni O5'
_chemical_formula_weight         473.11
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.17(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.915(2)
_cell_length_b                   12.442(3)
_cell_length_c                   17.504(4)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.48
_cell_volume                     2093.6(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18519
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.7137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                3293
_reflns_number_total             4771
_reflns_threshold_expression     I>\2s(I)
_cod_data_source_file            b714491a.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2093.6(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7201746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.46078(4) 0.29009(4) 0.179981(19) 0.06205(17) Uani 1 1 d . . .
C1 C 0.1579(4) 0.1631(3) 0.27793(17) 0.0646(8) Uani 1 1 d . . .
C2 C 0.2300(4) 0.1282(3) 0.35174(17) 0.0645(8) Uani 1 1 d . . .
H2 H 0.3239 0.1448 0.3697 0.077 Uiso 1 1 calc R . .
C3 C 0.1645(4) 0.0690(3) 0.39942(18) 0.0677(8) Uani 1 1 d . . .
C4 C 0.0235(4) 0.0456(4) 0.3717(2) 0.0851(11) Uani 1 1 d . . .
H4 H -0.0215 0.0050 0.4026 0.102 Uiso 1 1 calc R . .
C5 C -0.0496(4) 0.0816(4) 0.2993(2) 0.0882(12) Uani 1 1 d . . .
H5 H -0.1440 0.0665 0.2820 0.106 Uiso 1 1 calc R . .
C6 C 0.0165(4) 0.1401(3) 0.2520(2) 0.0759(10) Uani 1 1 d . . .
H6 H -0.0334 0.1642 0.2029 0.091 Uiso 1 1 calc R . .
C7 C 0.2320(4) 0.2207(3) 0.22470(19) 0.0747(10) Uani 1 1 d . . .
C8 C 0.2431(4) 0.0337(3) 0.47930(18) 0.0706(9) Uani 1 1 d . . .
C9 C 0.3121(4) 0.1073(3) 0.53310(18) 0.0707(9) Uani 1 1 d . . .
H9 H 0.3112 0.1787 0.5172 0.085 Uiso 1 1 calc R . .
C10 C 0.3856(5) -0.0193(3) 0.6292(2) 0.0850(11) Uani 1 1 d . . .
H10 H 0.4344 -0.0379 0.6799 0.102 Uiso 1 1 calc R . .
C11 C 0.3207(6) -0.0978(4) 0.5792(3) 0.1104(16) Uani 1 1 d . . .
H11 H 0.3253 -0.1689 0.5961 0.133 Uiso 1 1 calc R . .
C12 C 0.2486(6) -0.0721(3) 0.5040(2) 0.1016(15) Uani 1 1 d . . .
H12 H 0.2037 -0.1255 0.4699 0.122 Uiso 1 1 calc R . .
C13 C 0.6515(3) 0.0558(3) 0.07987(16) 0.0596(7) Uani 1 1 d . . .
C14 C 0.7128(3) -0.0420(3) 0.10828(18) 0.0685(9) Uani 1 1 d . . .
H14 H 0.7097 -0.0657 0.1582 0.082 Uiso 1 1 calc R . .
C15 C 0.7779(4) -0.1035(3) 0.0625(2) 0.0727(9) Uani 1 1 d . . .
H15 H 0.8168 -0.1693 0.0812 0.087 Uiso 1 1 calc R . .
C16 C 0.7860(4) -0.0681(3) -0.01122(19) 0.0675(8) Uani 1 1 d . . .
H16 H 0.8314 -0.1097 -0.0414 0.081 Uiso 1 1 calc R . .
C17 C 0.7264(3) 0.0296(3) -0.04034(16) 0.0572(7) Uani 1 1 d . . .
C18 C 0.6584(3) 0.0904(3) 0.00552(16) 0.0584(7) Uani 1 1 d . . .
H18 H 0.6169 0.1551 -0.0139 0.070 Uiso 1 1 calc R . .
C19 C 0.5842(4) 0.1234(3) 0.12998(17) 0.0687(9) Uani 1 1 d . . .
C20 C 0.7397(3) 0.0689(2) -0.11843(16) 0.0553(7) Uani 1 1 d . . .
C21 C 0.8638(4) 0.0651(3) -0.1402(2) 0.0700(9) Uani 1 1 d . . .
H21 H 0.9421 0.0357 -0.1062 0.084 Uiso 1 1 calc R . .
C22 C 0.8723(4) 0.1047(3) -0.2119(2) 0.0771(10) Uani 1 1 d . . .
H22 H 0.9566 0.1040 -0.2263 0.092 Uiso 1 1 calc R . .
C23 C 0.7559(4) 0.1452(3) -0.26188(19) 0.0689(9) Uani 1 1 d . . .
H23 H 0.7620 0.1712 -0.3107 0.083 Uiso 1 1 calc R . .
C24 C 0.6259(3) 0.1116(3) -0.17214(15) 0.0581(7) Uani 1 1 d . . .
H24 H 0.5410 0.1148 -0.1585 0.070 Uiso 1 1 calc R . .
N1 N 0.3807(3) 0.0834(3) 0.60717(15) 0.0733(8) Uani 1 1 d . . .
N2 N 0.6334(3) 0.1486(2) -0.24302(13) 0.0621(7) Uani 1 1 d . . .
O1 O 0.3584(3) 0.2463(3) 0.25556(15) 0.0885(8) Uani 1 1 d . . .
O2 O 0.1743(4) 0.2376(3) 0.15588(15) 0.1154(11) Uani 1 1 d . . .
O3 O 0.5274(3) 0.2119(2) 0.10011(13) 0.0765(7) Uani 1 1 d . . .
O4 O 0.5845(3) 0.0943(2) 0.19733(13) 0.0972(9) Uani 1 1 d . . .
O1W O 0.977(2) 0.2466(13) 0.023(2) 0.649(15) Uani 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
_geom_angle_publ_flag
O1 Ni1 O3 132.69(13) . . ?
O1 Ni1 N2 98.57(11) . 4_566 ?
O3 Ni1 N2 106.42(11) . 4_566 ?
O1 Ni1 N1 116.87(13) . 4_565 ?
O3 Ni1 N1 94.87(11) . 4_565 ?
N2 Ni1 N1 104.83(11) 4_566 4_565 ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C7 120.6(3) . . ?
C6 C1 C7 120.1(3) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 C8 120.4(3) . . ?
C4 C3 C8 120.9(3) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O2 C7 O1 123.3(3) . . ?
O2 C7 C1 120.9(3) . . ?
O1 C7 C1 115.8(3) . . ?
C9 C8 C12 116.5(3) . . ?
C9 C8 C3 120.4(3) . . ?
C12 C8 C3 123.1(3) . . ?
N1 C9 C8 124.4(3) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N1 C10 C11 121.6(4) . . ?
N1 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C8 119.5(4) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 C19 120.7(3) . . ?
C14 C13 C19 120.1(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 C20 121.0(3) . . ?
C16 C17 C20 119.9(3) . . ?
C13 C18 C17 120.9(3) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O4 C19 O3 122.6(4) . . ?
O4 C19 C13 120.1(4) . . ?
O3 C19 C13 117.3(3) . . ?
C21 C20 C24 117.4(3) . . ?
C21 C20 C17 122.0(3) . . ?
C24 C20 C17 120.6(3) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
N2 C23 C22 122.1(3) . . ?
N2 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
N2 C24 C20 122.6(3) . . ?
N2 C24 H24 118.7 . . ?
C20 C24 H24 118.7 . . ?
C10 N1 C9 117.8(3) . . ?
C10 N1 Ni1 125.0(2) . 4_566 ?
C9 N1 Ni1 117.1(2) . 4_566 ?
C23 N2 C24 118.5(3) . . ?
C23 N2 Ni1 120.9(2) . 4_565 ?
C24 N2 Ni1 120.6(2) . 4_565 ?
C7 O1 Ni1 114.0(2) . . ?
C19 O3 Ni1 109.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.933(3) . ?
Ni1 O3 1.947(2) . ?
Ni1 N2 2.049(3) 4_566 ?
Ni1 N1 2.058(3) 4_565 ?
C1 C2 1.384(4) . ?
C1 C6 1.393(5) . ?
C1 C7 1.503(5) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(5) . ?
C3 C8 1.491(5) . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.219(4) . ?
C7 O1 1.277(4) . ?
C8 C9 1.371(5) . ?
C8 C12 1.382(5) . ?
C9 N1 1.342(4) . ?
C9 H9 0.9300 . ?
C10 N1 1.332(5) . ?
C10 C11 1.363(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.388(4) . ?
C13 C14 1.396(5) . ?
C13 C19 1.486(5) . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(4) . ?
C17 C20 1.488(4) . ?
C18 H18 0.9300 . ?
C19 O4 1.233(4) . ?
C19 O3 1.288(4) . ?
C20 C21 1.376(5) . ?
C20 C24 1.386(4) . ?
C21 C22 1.370(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.362(5) . ?
C22 H22 0.9300 . ?
C23 N2 1.335(4) . ?
C23 H23 0.9300 . ?
C24 N2 1.343(4) . ?
C24 H24 0.9300 . ?
N1 Ni1 2.058(3) 4_566 ?
N2 Ni1 2.049(3) 4_565 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(5) . . . . ?
C7 C1 C2 C3 -175.9(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C2 C3 C8 -179.0(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C8 C3 C4 C5 177.7(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C7 C1 C6 C5 176.2(4) . . . . ?
C2 C1 C7 O2 169.2(4) . . . . ?
C6 C1 C7 O2 -8.0(6) . . . . ?
C2 C1 C7 O1 -8.4(5) . . . . ?
C6 C1 C7 O1 174.4(4) . . . . ?
C2 C3 C8 C9 55.1(5) . . . . ?
C4 C3 C8 C9 -123.5(4) . . . . ?
C2 C3 C8 C12 -126.4(4) . . . . ?
C4 C3 C8 C12 55.0(6) . . . . ?
C12 C8 C9 N1 -1.3(6) . . . . ?
C3 C8 C9 N1 177.3(3) . . . . ?
N1 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 C8 0.4(8) . . . . ?
C9 C8 C12 C11 0.1(7) . . . . ?
C3 C8 C12 C11 -178.5(4) . . . . ?
C18 C13 C14 C15 -0.6(5) . . . . ?
C19 C13 C14 C15 -178.5(3) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C15 C16 C17 C20 177.9(3) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C19 C13 C18 C17 177.3(3) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C20 C17 C18 C13 -177.1(3) . . . . ?
C18 C13 C19 O4 -176.6(3) . . . . ?
C14 C13 C19 O4 1.3(5) . . . . ?
C18 C13 C19 O3 3.3(5) . . . . ?
C14 C13 C19 O3 -178.8(3) . . . . ?
C18 C17 C20 C21 133.2(3) . . . . ?
C16 C17 C20 C21 -44.9(4) . . . . ?
C18 C17 C20 C24 -46.3(4) . . . . ?
C16 C17 C20 C24 135.5(3) . . . . ?
C24 C20 C21 C22 1.3(5) . . . . ?
C17 C20 C21 C22 -178.3(3) . . . . ?
C20 C21 C22 C23 -1.6(6) . . . . ?
C21 C22 C23 N2 0.7(6) . . . . ?
C21 C20 C24 N2 0.0(5) . . . . ?
C17 C20 C24 N2 179.6(3) . . . . ?
C11 C10 N1 C9 -1.4(6) . . . . ?
C11 C10 N1 Ni1 174.8(3) . . . 4_566 ?
C8 C9 N1 C10 2.0(6) . . . . ?
C8 C9 N1 Ni1 -174.5(3) . . . 4_566 ?
C22 C23 N2 C24 0.5(5) . . . . ?
C22 C23 N2 Ni1 -179.9(3) . . . 4_565 ?
C20 C24 N2 C23 -0.9(5) . . . . ?
C20 C24 N2 Ni1 179.6(2) . . . 4_565 ?
O2 C7 O1 Ni1 -10.7(5) . . . . ?
C1 C7 O1 Ni1 166.8(2) . . . . ?
O3 Ni1 O1 C7 -69.7(3) . . . . ?
N2 Ni1 O1 C7 168.5(3) 4_566 . . . ?
N1 Ni1 O1 C7 57.0(3) 4_565 . . . ?
O4 C19 O3 Ni1 4.4(4) . . . . ?
C13 C19 O3 Ni1 -175.4(2) . . . . ?
O1 Ni1 O3 C19 -45.1(3) . . . . ?
N2 Ni1 O3 C19 73.7(2) 4_566 . . . ?
N1 Ni1 O3 C19 -179.2(2) 4_565 . . . ?
