#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/67/2216749.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216749
loop_
_publ_author_name
'Kai Zhao'
'Xian-Hong Yin'
'Yu Feng'
'Jie Zhu'
_publ_section_title
;Bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)picolinato-κ²N,O]cobalt(II)
 2.5-hydrate
;
_journal_coeditor_code           SG2193
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3024
_journal_page_last               m3024
_journal_paper_doi               10.1107/S1600536807050623
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Co (C11 H9 Cl1 N3 O2)2], 2.5H2 O1'
_chemical_formula_moiety         'C22 H18 Cl2 Co N6 O4, 2.5H2 O1'
_chemical_formula_sum            'C22 H23 Cl2 Co N6 O6.5'
_chemical_formula_weight         605.29
_chemical_name_systematic
;
Bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl-\kN²)picolinato-
κ²N,O]cobalt(II) 2.5-hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 129.875(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.207(3)
_cell_length_b                   11.7918(13)
_cell_length_c                   14.3531(16)
_cell_measurement_reflns_used    3006
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.037
_cell_measurement_theta_min      2.17
_cell_volume                     2624.7(6)
_computing_cell_refinement       'SMART (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6384
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.7298
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.483
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0408
_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)+(0.0624P)²+4.5881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                1847
_reflns_number_total             2305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2193.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2624.6(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C22 H23 Cl2 Co N6 O6.50'
_cod_database_code               2216749
_cod_database_fobs_code          2216749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Co Co1 0.0000 0.88230(5) 0.2500 0.0405(2) Uani d S 1
Cl Cl1 0.25684(7) 0.64296(9) 0.28440(10) 0.0700(3) Uani d . 1
N N1 0.12695(15) 0.8634(2) 0.3226(2) 0.0400(6) Uani d . 1
N N2 0.15784(15) 1.0115(2) 0.4471(2) 0.0435(6) Uani d . 1
N N3 0.06995(15) 1.0112(2) 0.3844(2) 0.0450(7) Uani d . 1
O O1 -0.00805(14) 0.7608(2) 0.1370(2) 0.0584(7) Uani d . 1
O O2 0.0689(2) 0.6276(3) 0.1374(4) 0.0981(12) Uani d . 1
O O3 0.0520(3) 0.4551(4) 0.4323(5) 0.160(2) Uani d . 1
H H3A 0.0156 0.5085 0.4053 0.192 Uiso d R 1
H H3B 0.0605 0.4261 0.4934 0.192 Uiso d R 1
O O4 0.0000 0.3204(11) 0.2500 0.118(4) Uani d SP 0.50
H H4A 0.0167 0.3626 0.3096 0.142 Uiso d PR 0.50
C C1 0.0613(2) 0.7152(3) 0.1753(3) 0.0539(9) Uani d . 1
C C2 0.1436(2) 0.7766(3) 0.2794(3) 0.0430(7) Uani d . 1
C C3 0.2279(2) 0.7541(3) 0.3311(3) 0.0489(8) Uani d . 1
C C4 0.2934(2) 0.8222(4) 0.4251(3) 0.0614(10) Uani d . 1
H H4 0.3503 0.8078 0.4595 0.074 Uiso calc R 1
C C5 0.2752(2) 0.9103(4) 0.4677(3) 0.0578(10) Uani d . 1
H H5 0.3186 0.9570 0.5300 0.069 Uiso calc R 1
C C6 0.18908(19) 0.9271(3) 0.4139(3) 0.0427(7) Uani d . 1
C C7 0.2919(3) 1.1245(4) 0.6132(4) 0.0785(14) Uani d . 1
H H7A 0.3035 1.1900 0.6614 0.118 Uiso calc R 1
H H7B 0.3102 1.1387 0.5669 0.118 Uiso calc R 1
H H7C 0.3227 1.0604 0.6654 0.118 Uiso calc R 1
C C8 0.1967(2) 1.1000(3) 0.5284(3) 0.0519(9) Uani d . 1
C C9 0.1331(2) 1.1555(4) 0.5161(3) 0.0591(10) Uani d . 1
H H9 0.1394 1.2196 0.5589 0.071 Uiso calc R 1
C C10 0.0553(2) 1.0985(3) 0.4266(3) 0.0503(8) Uani d . 1
C C11 -0.0344(3) 1.1244(4) 0.3785(4) 0.0714(12) Uani d . 1
H H11A -0.0708 1.0598 0.3348 0.107 Uiso calc R 1
H H11B -0.0565 1.1885 0.3250 0.107 Uiso calc R 1
H H11C -0.0333 1.1413 0.4448 0.107 Uiso calc R 1
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'
Co Co 0.3494 0.9721 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 Co1 N1 . 2 167.64(15)
N1 Co1 O1 . . 76.79(9)
N1 Co1 O1 2 . 94.64(10)
N1 Co1 O1 . 2 94.64(10)
N1 Co1 O1 2 2 76.79(9)
O1 Co1 O1 . 2 93.49(16)
N1 Co1 N3 . . 74.49(10)
N1 Co1 N3 2 . 114.91(10)
O1 Co1 N3 . . 150.26(9)
O1 Co1 N3 2 . 96.33(11)
N1 Co1 N3 . 2 114.91(10)
N1 Co1 N3 2 2 74.49(10)
O1 Co1 N3 . 2 96.33(11)
O1 Co1 N3 2 2 150.26(9)
N3 Co1 N3 . 2 88.88(15)
C6 N1 C2 . . 122.0(3)
C6 N1 Co1 . . 121.3(2)
C2 N1 Co1 . . 116.4(2)
C8 N2 N3 . . 110.5(3)
C8 N2 C6 . . 133.1(3)
N3 N2 C6 . . 116.3(2)
C10 N3 N2 . . 105.8(3)
C10 N3 Co1 . . 139.3(2)
N2 N3 Co1 . . 114.9(2)
C1 O1 Co1 . . 116.5(2)
H3A O3 H3B . . 108.2
O2 C1 O1 . . 126.4(4)
O2 C1 C2 . . 117.8(3)
O1 C1 C2 . . 115.8(3)
N1 C2 C3 . . 119.0(3)
N1 C2 C1 . . 112.0(3)
C3 C2 C1 . . 129.0(3)
C2 C3 C4 . . 119.4(3)
C2 C3 Cl1 . . 122.9(3)
C4 C3 Cl1 . . 117.7(3)
C5 C4 C3 . . 120.7(3)
C5 C4 H4 . . 119.6
C3 C4 H4 . . 119.6
C4 C5 C6 . . 117.2(3)
C4 C5 H5 . . 121.4
C6 C5 H5 . . 121.4
N1 C6 C5 . . 121.5(3)
N1 C6 N2 . . 112.9(3)
C5 C6 N2 . . 125.6(3)
C8 C7 H7A . . 109.5
C8 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C8 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C9 C8 N2 . . 106.2(3)
C9 C8 C7 . . 129.0(4)
N2 C8 C7 . . 124.8(3)
C8 C9 C10 . . 107.5(3)
C8 C9 H9 . . 126.3
C10 C9 H9 . . 126.3
N3 C10 C9 . . 110.0(3)
N3 C10 C11 . . 120.5(3)
C9 C10 C11 . . 129.5(3)
C10 C11 H11A . . 109.5
C10 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C10 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Co1 N1 . 2.071(2)
Co1 N1 2 2.071(2)
Co1 O1 . 2.090(2)
Co1 O1 2 2.090(2)
Co1 N3 . 2.129(3)
Co1 N3 2 2.129(3)
Cl1 C3 . 1.735(4)
N1 C6 . 1.323(4)
N1 C2 . 1.346(4)
N2 C8 . 1.375(4)
N2 N3 . 1.384(3)
N2 C6 . 1.414(4)
N3 C10 . 1.321(4)
O1 C1 . 1.252(4)
O2 C1 . 1.221(4)
O3 H3A . 0.8500
O3 H3B . 0.8502
O4 H4A . 0.8500
C1 C2 . 1.529(5)
C2 C3 . 1.380(4)
C3 C4 . 1.388(5)
C4 C5 . 1.371(6)
C4 H4 . 0.9300
C5 C6 . 1.393(4)
C5 H5 . 0.9300
C7 C8 . 1.504(5)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C9 . 1.350(5)
C9 C10 . 1.408(5)
C9 H9 . 0.9300
C10 C11 . 1.499(5)
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 2_555 0.850 1.981 2.825(8) 171.52 yes
O3 H3B O2 6_566 0.850 2.063 2.907(8) 171.96 yes
O4 H4A O3 1_555 0.850 1.786 2.636(8) 178.10 yes
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_site_symmetry_1
_geom_torsion
N1 Co1 N1 C6 2 -137.3(2)
O1 Co1 N1 C6 . 175.8(3)
O1 Co1 N1 C6 2 -91.7(3)
N3 Co1 N1 C6 . 3.6(2)
N3 Co1 N1 C6 2 84.9(3)
N1 Co1 N1 C2 2 36.9(2)
O1 Co1 N1 C2 . -10.1(2)
O1 Co1 N1 C2 2 82.4(2)
N3 Co1 N1 C2 . 177.7(2)
N3 Co1 N1 C2 2 -101.0(2)
C8 N2 N3 C10 . 0.1(4)
C6 N2 N3 C10 . -177.7(3)
C8 N2 N3 Co1 . 177.8(2)
C6 N2 N3 Co1 . 0.0(3)
N1 Co1 N3 C10 . 174.9(4)
N1 Co1 N3 C10 2 -13.7(4)
O1 Co1 N3 C10 . 159.4(3)
O1 Co1 N3 C10 2 -92.1(4)
N3 Co1 N3 C10 2 58.6(3)
N1 Co1 N3 N2 . -1.7(2)
N1 Co1 N3 N2 2 169.7(2)
O1 Co1 N3 N2 . -17.2(4)
O1 Co1 N3 N2 2 91.4(2)
N3 Co1 N3 N2 2 -118.0(2)
N1 Co1 O1 C1 . 15.0(3)
N1 Co1 O1 C1 2 -156.0(3)
O1 Co1 O1 C1 2 -79.0(3)
N3 Co1 O1 C1 . 30.3(4)
N3 Co1 O1 C1 2 129.1(3)
Co1 O1 C1 O2 . 163.4(4)
Co1 O1 C1 C2 . -16.8(4)
C6 N1 C2 C3 . -0.7(5)
Co1 N1 C2 C3 . -174.8(2)
C6 N1 C2 C1 . 179.1(3)
Co1 N1 C2 C1 . 5.0(3)
O2 C1 C2 N1 . -172.3(4)
O1 C1 C2 N1 . 7.8(5)
O2 C1 C2 C3 . 7.4(6)
O1 C1 C2 C3 . -172.4(3)
N1 C2 C3 C4 . -0.9(5)
C1 C2 C3 C4 . 179.4(3)
N1 C2 C3 Cl1 . 178.8(2)
C1 C2 C3 Cl1 . -0.9(5)
C2 C3 C4 C5 . 0.8(6)
Cl1 C3 C4 C5 . -179.0(3)
C3 C4 C5 C6 . 0.8(6)
C2 N1 C6 C5 . 2.4(5)
Co1 N1 C6 C5 . 176.2(3)
C2 N1 C6 N2 . -178.4(3)
Co1 N1 C6 N2 . -4.6(4)
C4 C5 C6 N1 . -2.4(5)
C4 C5 C6 N2 . 178.5(3)
C8 N2 C6 N1 . -174.4(3)
N3 N2 C6 N1 . 2.8(4)
C8 N2 C6 C5 . 4.8(6)
N3 N2 C6 C5 . -178.0(3)
N3 N2 C8 C9 . -0.3(4)
C6 N2 C8 C9 . 177.0(3)
N3 N2 C8 C7 . 178.8(4)
C6 N2 C8 C7 . -3.9(6)
N2 C8 C9 C10 . 0.4(4)
C7 C8 C9 C10 . -178.7(4)
N2 N3 C10 C9 . 0.1(4)
Co1 N3 C10 C9 . -176.7(3)
N2 N3 C10 C11 . -180.0(3)
Co1 N3 C10 C11 . 3.3(6)
C8 C9 C10 N3 . -0.3(5)
C8 C9 C10 C11 . 179.8(4)
