#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:50:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179599 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506329.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_4506329
loop_
_publ_author_name
'Gu, Jinzhong'
'Gao, Zhuqing'
'Tang, Yu'
_publ_section_title
;
 pH and Auxiliary Ligand Influence on the Structural Variations of
 5(2′-Carboxylphenyl) Nicotate Coordination Polymers
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3312
_journal_paper_doi               10.1021/cg300442b
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C25 H17 Co N3 O5'
_chemical_formula_weight         498.35
_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                76.185(6)
_cell_angle_beta                 89.248(6)
_cell_angle_gamma                67.319(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4178(6)
_cell_length_b                   10.2005(7)
_cell_length_c                   12.0937(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1036.89(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8658
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  0.8177
_exptl_absorpt_correction_T_min  0.7920
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needl
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0357
_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)+(0.0255P)²+0.3914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                3157
_reflns_number_total             3876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300442b_si_002.cif
_cod_data_source_block           p1_(Compound_6)
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1036.89(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4506329
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
Co1 Co 0.22913(4) 0.57007(3) 0.27105(3) 0.02427(11) Uani 1 1 d .
C5 C 0.2873(3) 0.3202(2) 0.16324(19) 0.0257(5) Uani 1 1 d .
C4 C 0.3564(3) 0.1941(3) 0.1224(2) 0.0325(6) Uani 1 1 d .
C1 C 0.5214(3) 0.3279(3) 0.2025(2) 0.0387(7) Uani 1 1 d .
H1 H 0.5789 0.3709 0.2310 0.046 Uiso 1 1 calc R
C6 C 0.2604(4) 0.1317(3) 0.0831(2) 0.0417(7) Uani 1 1 d .
H6 H 0.3063 0.0440 0.0615 0.050 Uiso 1 1 calc R
C2 C 0.5996(3) 0.2060(3) 0.1590(2) 0.0441(7) Uani 1 1 d .
H2 H 0.7062 0.1715 0.1562 0.053 Uiso 1 1 calc R
C9 C 0.1223(3) 0.3883(2) 0.15855(18) 0.0236(5) Uani 1 1 d .
C3 C 0.5180(4) 0.1388(3) 0.1209(2) 0.0417(7) Uani 1 1 d .
H3 H 0.5689 0.0561 0.0939 0.050 Uiso 1 1 calc R
C8 C 0.0308(3) 0.3304(3) 0.11190(19) 0.0279(6) Uani 1 1 d .
C7 C 0.1050(4) 0.1967(3) 0.0767(2) 0.0392(7) Uani 1 1 d .
H7 H 0.0455 0.1548 0.0492 0.047 Uiso 1 1 calc R
C10 C -0.1299(3) 0.4085(3) 0.1014(2) 0.0355(6) Uani 1 1 d .
H10 H -0.1944 0.3753 0.0691 0.043 Uiso 1 1 calc R
C12 C -0.0912(3) 0.5801(3) 0.1877(2) 0.0322(6) Uani 1 1 d .
H12 H -0.1343 0.6641 0.2144 0.039 Uiso 1 1 calc R
N2 N 0.0606(2) 0.5114(2) 0.19789(16) 0.0249(4) Uani 1 1 d .
C24 C 0.1063(3) 0.0368(2) 0.64448(19) 0.0242(5) Uani 1 1 d .
C19 C 0.2130(3) 0.0625(2) 0.5703(2) 0.0253(5) Uani 1 1 d .
C21 C 0.2540(3) -0.1591(3) 0.5132(2) 0.0385(7) Uani 1 1 d .
H21 H 0.3023 -0.2227 0.4679 0.046 Uiso 1 1 calc R
C25 C 0.0183(3) 0.1382(3) 0.7179(2) 0.0272(6) Uani 1 1 d .
O4 O 0.0319(2) 0.0833(2) 0.82305(15) 0.0479(5) Uani 1 1 d .
C23 C 0.0769(3) -0.0890(2) 0.6521(2) 0.0304(6) Uani 1 1 d .
H23 H 0.0074 -0.1080 0.7023 0.036 Uiso 1 1 calc R
C20 C 0.2868(3) -0.0344(3) 0.5076(2) 0.0307(6) Uani 1 1 d .
H20 H 0.3602 -0.0181 0.4603 0.037 Uiso 1 1 calc R
C22 C 0.1495(3) -0.1858(3) 0.5864(2) 0.0353(6) Uani 1 1 d .
H22 H 0.1277 -0.2685 0.5916 0.042 Uiso 1 1 calc R
C17 C 0.2557(3) 0.1920(2) 0.5600(2) 0.0249(5) Uani 1 1 d .
C14 C 0.3973(3) 0.3135(2) 0.62791(19) 0.0222(5) Uani 1 1 d .
C16 C 0.3480(3) 0.1992(2) 0.64497(19) 0.0251(5) Uani 1 1 d .
H16 H 0.3769 0.1270 0.7136 0.030 Uiso 1 1 calc R
N3 N 0.2598(2) 0.4161(2) 0.44033(16) 0.0252(5) Uani 1 1 d .
C18 C 0.2160(3) 0.3022(2) 0.4591(2) 0.0273(6) Uani 1 1 d .
H18 H 0.1559 0.2970 0.4012 0.033 Uiso 1 1 calc R
C13 C 0.3475(3) 0.4201(2) 0.52498(19) 0.0236(5) Uani 1 1 d .
H13 H 0.3768 0.4992 0.5140 0.028 Uiso 1 1 calc R
C11 C -0.1909(3) 0.5330(3) 0.1386(2) 0.0353(6) Uani 1 1 d .
H11 H -0.2972 0.5861 0.1317 0.042 Uiso 1 1 calc R
N1 N 0.3694(2) 0.3848(2) 0.20487(17) 0.0279(5) Uani 1 1 d .
C15 C 0.5113(3) 0.3161(2) 0.7137(2) 0.0238(5) Uani 1 1 d .
O2 O 0.5349(2) 0.23251(19) 0.81085(14) 0.0372(5) Uani 1 1 d .
O1 O 0.5746(2) 0.40533(18) 0.67702(14) 0.0334(4) Uani 1 1 d .
O3 O -0.0636(2) 0.26871(17) 0.66667(14) 0.0323(4) Uani 1 1 d .
O5 O 0.2168(3) 0.7254(2) 0.10982(15) 0.0328(4) Uani 1 1 d D
H1W H 0.135(3) 0.797(3) 0.118(3) 0.099(15) Uiso 1 1 d D
H2W H 0.295(3) 0.742(3) 0.122(3) 0.064(11) Uiso 1 1 d 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'
Co Co 0.3494 0.9721 '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'
N N 0.0061 0.0033 '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
O3 Co1 O1 99.03(7) 2_566 2_666
O3 Co1 N2 93.54(7) 2_566 .
O1 Co1 N2 167.33(7) 2_666 .
O3 Co1 O5 91.92(7) 2_566 .
O1 Co1 O5 88.11(7) 2_666 .
N2 Co1 O5 89.94(7) . .
O3 Co1 N1 169.23(7) 2_566 .
O1 Co1 N1 91.18(7) 2_666 .
N2 Co1 N1 76.37(7) . .
O5 Co1 N1 91.82(7) . .
O3 Co1 N3 88.52(7) 2_566 .
O1 Co1 N3 86.60(7) 2_666 .
N2 Co1 N3 95.30(7) . .
O5 Co1 N3 174.70(7) . .
N1 Co1 N3 88.70(7) . .
N1 C5 C4 123.2(2) . .
N1 C5 C9 117.4(2) . .
C4 C5 C9 119.4(2) . .
C5 C4 C3 116.8(2) . .
C5 C4 C6 119.1(2) . .
C3 C4 C6 124.1(2) . .
N1 C1 C2 123.1(3) . .
N1 C1 H1 118.5 . .
C2 C1 H1 118.5 . .
C7 C6 C4 121.6(2) . .
C7 C6 H6 119.2 . .
C4 C6 H6 119.2 . .
C3 C2 C1 119.2(3) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
N2 C9 C8 122.7(2) . .
N2 C9 C5 117.2(2) . .
C8 C9 C5 120.1(2) . .
C2 C3 C4 120.1(2) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C10 C8 C9 117.4(2) . .
C10 C8 C7 123.5(2) . .
C9 C8 C7 119.1(2) . .
C6 C7 C8 120.4(2) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C11 C10 C8 119.7(2) . .
C11 C10 H10 120.1 . .
C8 C10 H10 120.1 . .
N2 C12 C11 123.4(2) . .
N2 C12 H12 118.3 . .
C11 C12 H12 118.3 . .
C12 N2 C9 117.7(2) . .
C12 N2 Co1 127.80(15) . .
C9 N2 Co1 114.50(16) . .
C19 C24 C23 118.7(2) . .
C19 C24 C25 124.09(19) . .
C23 C24 C25 117.2(2) . .
C20 C19 C24 120.2(2) . .
C20 C19 C17 117.6(2) . .
C24 C19 C17 122.2(2) . .
C22 C21 C20 119.3(2) . .
C22 C21 H21 120.3 . .
C20 C21 H21 120.3 . .
O4 C25 O3 126.2(2) . .
O4 C25 C24 116.9(2) . .
O3 C25 C24 116.8(2) . .
C22 C23 C24 121.1(2) . .
C22 C23 H23 119.5 . .
C24 C23 H23 119.5 . .
C19 C20 C21 121.0(2) . .
C19 C20 H20 119.5 . .
C21 C20 H20 119.5 . .
C21 C22 C23 119.6(2) . .
C21 C22 H22 120.2 . .
C23 C22 H22 120.2 . .
C18 C17 C16 117.7(2) . .
C18 C17 C19 120.2(2) . .
C16 C17 C19 121.8(2) . .
C16 C14 C13 117.4(2) . .
C16 C14 C15 121.4(2) . .
C13 C14 C15 121.01(19) . .
C17 C16 C14 120.2(2) . .
C17 C16 H16 119.9 . .
C14 C16 H16 119.9 . .
C13 N3 C18 116.9(2) . .
C13 N3 Co1 119.01(14) . .
C18 N3 Co1 123.22(15) . .
N3 C18 C17 123.6(2) . .
N3 C18 H18 118.2 . .
C17 C18 H18 118.2 . .
N3 C13 C14 124.10(19) . .
N3 C13 H13 117.9 . .
C14 C13 H13 117.9 . .
C10 C11 C12 119.0(2) . .
C10 C11 H11 120.5 . .
C12 C11 H11 120.5 . .
C1 N1 C5 117.7(2) . .
C1 N1 Co1 128.23(17) . .
C5 N1 Co1 114.10(16) . .
O2 C15 O1 126.3(2) . .
O2 C15 C14 118.63(19) . .
O1 C15 C14 115.0(2) . .
C15 O1 Co1 134.99(16) . 2_666
C25 O3 Co1 129.03(16) . 2_566
Co1 O5 H1W 99(3) . .
Co1 O5 H2W 99(2) . .
H1W O5 H2W 110(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O3 2.0700(17) 2_566
Co1 O1 2.0826(16) 2_666
Co1 N2 2.1636(19) .
Co1 O5 2.1712(18) .
Co1 N1 2.174(2) .
Co1 N3 2.2073(19) .
C5 N1 1.360(3) .
C5 C4 1.404(3) .
C5 C9 1.432(3) .
C4 C3 1.406(4) .
C4 C6 1.431(4) .
C1 N1 1.324(3) .
C1 C2 1.401(4) .
C1 H1 0.9300 .
C6 C7 1.348(4) .
C6 H6 0.9300 .
C2 C3 1.356(4) .
C2 H2 0.9300 .
C9 N2 1.363(3) .
C9 C8 1.405(3) .
C3 H3 0.9300 .
C8 C10 1.403(4) .
C8 C7 1.437(3) .
C7 H7 0.9300 .
C10 C11 1.360(3) .
C10 H10 0.9300 .
C12 N2 1.320(3) .
C12 C11 1.400(3) .
C12 H12 0.9300 .
C24 C19 1.396(3) .
C24 C23 1.396(3) .
C24 C25 1.517(3) .
C19 C20 1.360(3) .
C19 C17 1.501(3) .
C21 C22 1.377(4) .
C21 C20 1.407(3) .
C21 H21 0.9300 .
C25 O4 1.248(3) .
C25 O3 1.256(3) .
C23 C22 1.384(3) .
C23 H23 0.9300 .
C20 H20 0.9300 .
C22 H22 0.9300 .
C17 C18 1.387(3) .
C17 C16 1.388(3) .
C14 C16 1.384(3) .
C14 C13 1.388(3) .
C14 C15 1.515(3) .
C16 H16 0.9300 .
N3 C13 1.342(3) .
N3 C18 1.346(3) .
C18 H18 0.9300 .
C13 H13 0.9300 .
C11 H11 0.9300 .
C15 O2 1.240(3) .
C15 O1 1.265(3) .
O1 Co1 2.0826(16) 2_666
O3 Co1 2.0701(17) 2_566
O5 H1W 0.860(19) .
O5 H2W 0.839(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O4 0.860(19) 1.84(2) 2.672(3) 163(4) 2_566
O5 H2W O2 0.839(18) 1.937(19) 2.757(3) 166(3) 2_666
O5 H2W O1 0.839(18) 2.57(3) 2.959(3) 110(2) 2_666
