#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:43:19 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179259 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/79/4317982.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_4317982
loop_
_publ_author_name
'John M. Rowland'
'Marilyn M. Olmstead'
'Pradip K. Mascharak'
_publ_section_title
;
 Unusual Reactivity of Methylene Group Adjacent to Pyridine-2-Carboxamido
 Moiety in Iron(III) and Cobalt(III) Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2754
_journal_page_last               2760
_journal_paper_doi               10.1021/ic011197e
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C25 H20 Cl Co N6 O9'
_chemical_formula_weight         642.85
_chemical_name_common            '[Co(bpca)₂]ClO₄^.^CH₃OH'
_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                110.182(4)
_cell_angle_beta                 102.203(7)
_cell_angle_gamma                101.096(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8361(9)
_cell_length_b                   11.4944(12)
_cell_length_c                   14.4695(14)
_cell_measurement_reflns_used    743
_cell_measurement_temperature    91(2)
_cell_measurement_theta_max      31.4
_cell_measurement_theta_min      2.5
_cell_volume                     1290.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 5.10 (Sheldrick, 1994)'
_computing_publication_material  'SHELXTL 6.10 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL 6.10 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      91(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17067
_diffrn_reflns_theta_full        31.48
_diffrn_reflns_theta_max         31.48
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     'omitted 0,0,1 due to extinction'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²+1.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                6747
_reflns_number_total             7815
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic011197e_3.cif
_cod_data_source_block           mn1248
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4317982
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.57473(3) 0.81601(2) 0.731173(16) 0.01308(6) Uani 1 1 d . . .
O1 O 0.6672(2) 1.15629(15) 0.96659(11) 0.0382(4) Uani 1 1 d . . .
O2 O 0.7714(2) 0.97318(15) 1.03836(11) 0.0362(4) Uani 1 1 d . . .
O3 O 0.56734(15) 0.64582(12) 0.43874(9) 0.0178(2) Uani 1 1 d . . .
O4 O 0.28027(14) 0.51958(12) 0.47259(9) 0.0168(2) Uani 1 1 d . . .
N1 N 0.51176(16) 0.95429(13) 0.69967(10) 0.0149(3) Uani 1 1 d . . .
N2 N 0.64699(18) 0.94153(14) 0.86901(10) 0.0168(3) Uani 1 1 d . . .
N3 N 0.65563(17) 0.70862(14) 0.79563(11) 0.0155(3) Uani 1 1 d . . .
N4 N 0.77589(17) 0.85682(13) 0.69925(11) 0.0152(3) Uani 1 1 d . . .
N5 N 0.50096(16) 0.69212(13) 0.59271(10) 0.0141(2) Uani 1 1 d . . .
N6 N 0.35696(17) 0.74154(13) 0.73035(10) 0.0146(2) Uani 1 1 d . . .
C1 C 0.43904(19) 0.95074(16) 0.60698(12) 0.0160(3) Uani 1 1 d . . .
H1 H 0.4148 0.8734 0.5472 0.019 Uiso 1 1 calc R . .
C2 C 0.3982(2) 1.05753(18) 0.59622(13) 0.0185(3) Uani 1 1 d . . .
H2 H 0.3471 1.0528 0.5298 0.022 Uiso 1 1 calc R . .
C3 C 0.4326(2) 1.17085(18) 0.68316(14) 0.0210(3) Uani 1 1 d . . .
H3 H 0.4045 1.2442 0.6772 0.025 Uiso 1 1 calc R . .
C4 C 0.5089(2) 1.17483(18) 0.77900(14) 0.0230(3) Uani 1 1 d . . .
H4 H 0.5346 1.2512 0.8398 0.028 Uiso 1 1 calc R . .
C5 C 0.5468(2) 1.06558(16) 0.78428(13) 0.0186(3) Uani 1 1 d . . .
C6 C 0.6283(2) 1.06258(17) 0.88546(14) 0.0227(3) Uani 1 1 d . . .
C7 C 0.7166(2) 0.90686(17) 0.94605(13) 0.0219(3) Uani 1 1 d . . .
C8 C 0.7189(2) 0.76903(17) 0.90010(13) 0.0196(3) Uani 1 1 d . . .
C9 C 0.7823(3) 0.70761(19) 0.95901(15) 0.0264(4) Uani 1 1 d . . .
H9 H 0.8265 0.7519 1.0319 0.032 Uiso 1 1 calc R . .
C10 C 0.7802(3) 0.57923(19) 0.90940(15) 0.0262(4) Uani 1 1 d . . .
H10 H 0.8223 0.5344 0.9481 0.031 Uiso 1 1 calc R . .
C11 C 0.7159(2) 0.51819(18) 0.80317(15) 0.0218(3) Uani 1 1 d . . .
H11 H 0.7138 0.4309 0.7681 0.026 Uiso 1 1 calc R . .
C12 C 0.6545(2) 0.58546(16) 0.74800(13) 0.0177(3) Uani 1 1 d . . .
H12 H 0.6107 0.5432 0.6750 0.021 Uiso 1 1 calc R . .
C13 C 0.9200(2) 0.93848(17) 0.76354(13) 0.0195(3) Uani 1 1 d . . .
H13 H 0.9308 0.9833 0.8344 0.023 Uiso 1 1 calc R . .
C14 C 1.0532(2) 0.95877(18) 0.72889(15) 0.0229(4) Uani 1 1 d . . .
H14 H 1.1543 1.0163 0.7757 0.027 Uiso 1 1 calc R . .
C15 C 1.0380(2) 0.89470(19) 0.62560(15) 0.0231(4) Uani 1 1 d . . .
H15 H 1.1282 0.9089 0.6007 0.028 Uiso 1 1 calc R . .
C16 C 0.8898(2) 0.80928(17) 0.55854(14) 0.0195(3) Uani 1 1 d . . .
H16 H 0.8767 0.7636 0.4874 0.023 Uiso 1 1 calc R . .
C17 C 0.76207(19) 0.79278(16) 0.59831(12) 0.0150(3) Uani 1 1 d . . .
C18 C 0.59945(19) 0.70030(15) 0.53212(12) 0.0142(3) Uani 1 1 d . . .
C19 C 0.34809(19) 0.60652(15) 0.55751(12) 0.0138(3) Uani 1 1 d . . .
C20 C 0.27075(19) 0.63467(15) 0.64251(12) 0.0144(3) Uani 1 1 d . . .
C21 C 0.1215(2) 0.55924(17) 0.63191(13) 0.0175(3) Uani 1 1 d . . .
H21 H 0.0661 0.4830 0.5711 0.021 Uiso 1 1 calc R . .
C22 C 0.0531(2) 0.59665(18) 0.71208(14) 0.0202(3) Uani 1 1 d . . .
H22 H -0.0497 0.5465 0.7068 0.024 Uiso 1 1 calc R . .
C23 C 0.1379(2) 0.70813(18) 0.79930(13) 0.0194(3) Uani 1 1 d . . .
H23 H 0.0920 0.7371 0.8538 0.023 Uiso 1 1 calc R . .
C24 C 0.2910(2) 0.77792(16) 0.80705(13) 0.0171(3) Uani 1 1 d . . .
H24 H 0.3498 0.8530 0.8681 0.021 Uiso 1 1 calc R . .
Cl1 Cl 0.91226(5) 1.22911(4) 0.67679(3) 0.02265(9) Uani 1 1 d . . .
O5 O 0.9234(2) 1.31412(19) 0.77909(14) 0.0490(5) Uani 1 1 d . . .
O6 O 1.07190(17) 1.21827(15) 0.67425(12) 0.0307(3) Uani 1 1 d . . .
O7 O 0.8523(2) 1.28048(18) 0.60326(16) 0.0502(5) Uani 1 1 d . . .
O8 O 0.80500(17) 1.10354(14) 0.64929(12) 0.0291(3) Uani 1 1 d . . .
O9 O 1.3304(2) 1.38355(17) 0.86677(13) 0.0382(4) Uani 1 1 d . . .
H9A H 1.232(4) 1.331(3) 0.802(2) 0.046 Uiso 1 1 d . . .
C25 C 1.3376(3) 1.5157(2) 0.89312(18) 0.0332(4) Uani 1 1 d . . .
H25A H 1.2353 1.5289 0.9039 0.050 Uiso 1 1 calc R . .
H25B H 1.3560 1.5402 0.8370 0.050 Uiso 1 1 calc R . .
H25C H 1.4265 1.5695 0.9567 0.050 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'
Cl Cl 0.1484 0.1585 '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'
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
N5 Co1 N2 179.16(6) . . ?
N5 Co1 N3 97.82(6) . . ?
N2 Co1 N3 83.01(6) . . ?
N5 Co1 N4 83.26(6) . . ?
N2 Co1 N4 96.88(6) . . ?
N3 Co1 N4 90.15(6) . . ?
N5 Co1 N1 95.68(6) . . ?
N2 Co1 N1 83.49(6) . . ?
N3 Co1 N1 166.50(6) . . ?
N4 Co1 N1 91.25(6) . . ?
N5 Co1 N6 83.01(6) . . ?
N2 Co1 N6 96.86(6) . . ?
N3 Co1 N6 90.27(6) . . ?
N4 Co1 N6 166.20(6) . . ?
N1 Co1 N6 91.55(6) . . ?
C1 N1 C5 118.55(15) . . ?
C1 N1 Co1 127.99(12) . . ?
C5 N1 Co1 113.45(11) . . ?
C7 N2 C6 124.14(14) . . ?
C7 N2 Co1 118.15(12) . . ?
C6 N2 Co1 117.71(11) . . ?
C12 N3 C8 119.17(15) . . ?
C12 N3 Co1 126.84(12) . . ?
C8 N3 Co1 113.99(11) . . ?
C13 N4 C17 118.75(15) . . ?
C13 N4 Co1 128.19(12) . . ?
C17 N4 Co1 113.06(11) . . ?
C18 N5 C19 124.42(13) . . ?
C18 N5 Co1 117.19(11) . . ?
C19 N5 Co1 118.21(11) . . ?
C24 N6 C20 118.85(14) . . ?
C24 N6 Co1 127.57(12) . . ?
C20 N6 Co1 113.39(11) . . ?
N1 C1 C2 121.69(16) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.61(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.71(16) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.79(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.66(16) . . ?
N1 C5 C6 115.66(15) . . ?
C4 C5 C6 121.68(16) . . ?
O1 C6 N2 128.30(17) . . ?
O1 C6 C5 122.02(17) . . ?
N2 C6 C5 109.67(14) . . ?
O2 C7 N2 128.09(17) . . ?
O2 C7 C8 122.30(16) . . ?
N2 C7 C8 109.61(14) . . ?
N3 C8 C9 122.10(16) . . ?
N3 C8 C7 115.23(15) . . ?
C9 C8 C7 122.67(16) . . ?
C8 C9 C10 118.67(17) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 119.07(17) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.56(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N3 C12 C11 121.43(16) . . ?
N3 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N4 C13 C14 121.55(17) . . ?
N4 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 119.52(16) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.41(17) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 118.10(17) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
N4 C17 C16 122.65(15) . . ?
N4 C17 C18 115.74(14) . . ?
C16 C17 C18 121.61(15) . . ?
O3 C18 N5 128.44(15) . . ?
O3 C18 C17 121.99(15) . . ?
N5 C18 C17 109.56(13) . . ?
O4 C19 N5 128.18(15) . . ?
O4 C19 C20 122.49(15) . . ?
N5 C19 C20 109.33(13) . . ?
N6 C20 C21 122.24(15) . . ?
N6 C20 C19 115.39(14) . . ?
C21 C20 C19 122.36(14) . . ?
C20 C21 C22 118.87(16) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 118.70(16) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 119.76(16) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N6 C24 C23 121.47(15) . . ?
N6 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
O8 Cl1 O5 110.21(12) . . ?
O8 Cl1 O7 108.99(10) . . ?
O5 Cl1 O7 110.29(13) . . ?
O8 Cl1 O6 109.64(9) . . ?
O5 Cl1 O6 108.66(10) . . ?
O7 Cl1 O6 109.04(12) . . ?
C25 O9 H9A 106.7(17) . . ?
O9 C25 H25A 109.5 . . ?
O9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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
Co1 N5 1.8944(13) . ?
Co1 N2 1.8944(14) . ?
Co1 N3 1.9382(14) . ?
Co1 N4 1.9413(15) . ?
Co1 N1 1.9434(14) . ?
Co1 N6 1.9455(14) . ?
O1 C6 1.213(2) . ?
O2 C7 1.217(2) . ?
O3 C18 1.2183(19) . ?
O4 C19 1.2159(19) . ?
N1 C1 1.342(2) . ?
N1 C5 1.355(2) . ?
N2 C7 1.375(2) . ?
N2 C6 1.377(2) . ?
N3 C12 1.341(2) . ?
N3 C8 1.360(2) . ?
N4 C13 1.344(2) . ?
N4 C17 1.356(2) . ?
N5 C18 1.372(2) . ?
N5 C19 1.380(2) . ?
N6 C24 1.339(2) . ?
N6 C20 1.363(2) . ?
C1 C2 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.504(2) . ?
C7 C8 1.498(2) . ?
C8 C9 1.380(2) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.497(2) . ?
C19 C20 1.500(2) . ?
C20 C21 1.377(2) . ?
C21 C22 1.396(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
Cl1 O8 1.4345(14) . ?
Cl1 O5 1.4348(17) . ?
Cl1 O7 1.4411(17) . ?
Cl1 O6 1.4467(15) . ?
O9 C25 1.418(3) . ?
O9 H9A 1.03(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
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
O9 H9A O6 1.03(3) 1.91(3) 2.928(2) 171(3) .
O9 H9A O5 1.03(3) 2.64(3) 3.383(3) 129(2) .
O9 H9A Cl1 1.03(3) 2.78(3) 3.7646(18) 160(2) .
