#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:01:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179089 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/51/4305184.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_4305184
loop_
_publ_author_name
'Christopher W. Belock'
'Anil Çetin'
'Natalie V. Barone'
'Christopher J. Ziegler'
_publ_section_title
;
Transition Metal Coordination Chemistry
of N,N-Bis(2-{pyrid-2-ylethyl})hydroxylamine
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7114
_journal_page_last               7120
_journal_paper_doi               10.1021/ic702406n
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C14 H16 Co N5 O6'
_chemical_formula_weight         409.25
_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                 103.488(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4347(14)
_cell_length_b                   15.091(3)
_cell_length_c                   13.115(2)
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.48
_cell_volume                     1623.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13824
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.7619
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0316
_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)+(0.0371P)²+1.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                3470
_reflns_number_total             3827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic702406n-file002_5.cif
_cod_data_source_block           6
_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 
;
_cod_database_code               4305184
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
C1 C 0.0080(2) 0.31923(13) 0.64884(14) 0.0225(4) Uani 1 1 d . . .
C2 C -0.0802(2) 0.38337(14) 0.68605(15) 0.0254(4) Uani 1 1 d . . .
C3 C -0.0386(2) 0.47108(14) 0.67815(15) 0.0283(4) Uani 1 1 d . . .
C4 C 0.0910(2) 0.49070(13) 0.63529(15) 0.0266(4) Uani 1 1 d . . .
C5 C 0.1778(2) 0.42326(12) 0.60073(14) 0.0214(4) Uani 1 1 d . . .
C6 C 0.3228(2) 0.44617(12) 0.55791(16) 0.0246(4) Uani 1 1 d . . .
C7 C 0.4606(2) 0.37942(12) 0.57632(15) 0.0219(4) Uani 1 1 d . . .
C8 C 0.5656(2) 0.25046(13) 0.50039(16) 0.0237(4) Uani 1 1 d . . .
C9 C 0.5359(2) 0.18736(13) 0.40877(15) 0.0230(4) Uani 1 1 d . . .
C10 C 0.4235(2) 0.11026(12) 0.40862(13) 0.0190(3) Uani 1 1 d . . .
C11 C 0.4533(2) 0.03226(13) 0.35960(14) 0.0220(4) Uani 1 1 d . . .
C12 C 0.3502(2) -0.03901(13) 0.35369(14) 0.0237(4) Uani 1 1 d . . .
C13 C 0.2180(2) -0.03179(12) 0.39877(14) 0.0226(4) Uani 1 1 d . . .
C14 C 0.1942(2) 0.04696(12) 0.44559(14) 0.0203(3) Uani 1 1 d . . .
Co1 Co 0.22408(3) 0.231401(15) 0.527827(18) 0.01612(8) Uani 1 1 d . . .
H1 H -0.016(3) 0.2579(15) 0.6572(16) 0.018(5) Uiso 1 1 d . . .
H2 H -0.167(3) 0.3655(16) 0.7179(18) 0.030(6) Uiso 1 1 d . . .
H3 H -0.096(3) 0.5163(16) 0.7031(18) 0.031(6) Uiso 1 1 d . . .
H4 H 0.128(3) 0.5492(17) 0.6338(18) 0.032(6) Uiso 1 1 d . . .
H11 H 0.545(3) 0.0296(15) 0.3320(17) 0.026(6) Uiso 1 1 d . . .
H12 H 0.370(3) -0.0912(15) 0.3184(17) 0.024(5) Uiso 1 1 d . . .
H13 H 0.142(3) -0.0779(15) 0.3954(17) 0.024(5) Uiso 1 1 d . . .
H14 H 0.109(3) 0.0553(14) 0.4764(16) 0.021(5) Uiso 1 1 d . . .
H6A H 0.287(3) 0.4548(16) 0.4821(19) 0.032(6) Uiso 1 1 d . . .
H7A H 0.481(3) 0.3578(14) 0.6434(17) 0.022(5) Uiso 1 1 d . . .
H8A H 0.592(3) 0.2178(14) 0.5682(18) 0.025(6) Uiso 1 1 d . . .
H9A H 0.637(3) 0.1658(16) 0.4031(19) 0.035(6) Uiso 1 1 d . . .
H6B H 0.364(3) 0.5014(16) 0.5877(17) 0.027(6) Uiso 1 1 d . . .
H7B H 0.558(3) 0.4093(14) 0.5677(16) 0.019(5) Uiso 1 1 d . . .
H8B H 0.653(3) 0.2911(14) 0.4933(16) 0.020(5) Uiso 1 1 d . . .
H9B H 0.494(3) 0.2216(17) 0.345(2) 0.039(7) Uiso 1 1 d . . .
N1 N 0.13446(18) 0.33779(10) 0.60553(11) 0.0192(3) Uani 1 1 d . . .
N2 N 0.42128(18) 0.30525(10) 0.50110(12) 0.0208(3) Uani 1 1 d . . .
N3 N 0.29356(17) 0.11778(10) 0.45116(11) 0.0180(3) Uani 1 1 d . . .
N4 N 0.30669(18) 0.14011(10) 0.70627(11) 0.0199(3) Uani 1 1 d . . .
N5 N -0.04051(18) 0.26320(10) 0.38078(12) 0.0194(3) Uani 1 1 d . . .
O1 O 0.16844(16) 0.13100(9) 0.64516(10) 0.0248(3) Uani 1 1 d . . .
O2 O 0.39837(16) 0.19758(9) 0.68006(10) 0.0242(3) Uani 1 1 d . . .
O3 O 0.35219(17) 0.09521(9) 0.78633(10) 0.0253(3) Uani 1 1 d . . .
O4 O 0.09197(15) 0.30026(9) 0.37658(10) 0.0240(3) Uani 1 1 d . . .
O5 O -0.03246(15) 0.20600(8) 0.45268(10) 0.0219(3) Uani 1 1 d . . .
O6 O -0.16950(16) 0.28204(9) 0.31995(11) 0.0270(3) 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'
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'
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
N1 C1 C2 123.25(18) . . ?
N1 C1 H1 117.3(13) . . ?
C2 C1 H1 119.4(13) . . ?
C1 C2 C3 118.66(19) . . ?
C1 C2 H2 119.1(14) . . ?
C3 C2 H2 122.3(14) . . ?
C4 C3 C2 118.59(18) . . ?
C4 C3 H3 120.8(14) . . ?
C2 C3 H3 120.6(14) . . ?
C3 C4 C5 120.37(19) . . ?
C3 C4 H4 120.7(15) . . ?
C5 C4 H4 118.7(15) . . ?
N1 C5 C4 121.15(18) . . ?
N1 C5 C6 119.48(16) . . ?
C4 C5 C6 119.37(17) . . ?
C5 C6 C7 116.71(16) . . ?
C5 C6 H6A 109.2(13) . . ?
C7 C6 H6A 107.0(14) . . ?
C5 C6 H6B 107.5(13) . . ?
C7 C6 H6B 108.9(14) . . ?
H6A C6 H6B 107(2) . . ?
N2 C7 C6 110.66(15) . . ?
N2 C7 H7A 109.5(14) . . ?
C6 C7 H7A 111.0(14) . . ?
N2 C7 H7B 109.9(12) . . ?
C6 C7 H7B 108.2(13) . . ?
H7A C7 H7B 107.5(18) . . ?
N2 C8 C9 112.05(15) . . ?
N2 C8 H8A 106.5(13) . . ?
C9 C8 H8A 111.1(13) . . ?
N2 C8 H8B 107.0(13) . . ?
C9 C8 H8B 107.9(12) . . ?
H8A C8 H8B 112.1(18) . . ?
C10 C9 C8 118.57(15) . . ?
C10 C9 H9A 108.6(15) . . ?
C8 C9 H9A 107.4(15) . . ?
C10 C9 H9B 107.8(15) . . ?
C8 C9 H9B 107.9(15) . . ?
H9A C9 H9B 106(2) . . ?
N3 C10 C11 120.98(17) . . ?
N3 C10 C9 120.63(16) . . ?
C11 C10 C9 118.33(16) . . ?
C12 C11 C10 120.57(17) . . ?
C12 C11 H11 121.2(14) . . ?
C10 C11 H11 118.2(14) . . ?
C11 C12 C13 118.47(17) . . ?
C11 C12 H12 119.9(13) . . ?
C13 C12 H12 121.6(13) . . ?
C14 C13 C12 118.41(18) . . ?
C14 C13 H13 119.5(13) . . ?
C12 C13 H13 122.0(13) . . ?
N3 C14 C13 123.77(17) . . ?
N3 C14 H14 114.3(14) . . ?
C13 C14 H14 121.9(14) . . ?
N2 Co1 N1 93.62(6) . . ?
N2 Co1 N3 91.86(6) . . ?
N1 Co1 N3 174.50(6) . . ?
N2 Co1 O5 139.07(5) . . ?
N1 Co1 O5 85.63(5) . . ?
N3 Co1 O5 89.91(5) . . ?
N2 Co1 O2 83.64(5) . . ?
N1 Co1 O2 88.73(5) . . ?
N3 Co1 O2 92.37(5) . . ?
O5 Co1 O2 137.15(5) . . ?
N2 Co1 O1 139.47(5) . . ?
N1 Co1 O1 91.49(6) . . ?
N3 Co1 O1 84.65(5) . . ?
O5 Co1 O1 81.40(5) . . ?
O2 Co1 O1 56.29(5) . . ?
N2 Co1 O4 81.87(5) . . ?
N1 Co1 O4 85.24(5) . . ?
N3 Co1 O4 95.05(5) . . ?
O5 Co1 O4 57.25(5) . . ?
O2 Co1 O4 163.90(5) . . ?
O1 Co1 O4 138.65(5) . . ?
C5 N1 C1 117.93(16) . . ?
C5 N1 Co1 124.67(12) . . ?
C1 N1 Co1 116.61(12) . . ?
C8 N2 C7 111.84(14) . . ?
C8 N2 Co1 113.03(11) . . ?
C7 N2 Co1 110.74(11) . . ?
C10 N3 C14 117.79(15) . . ?
C10 N3 Co1 127.00(12) . . ?
C14 N3 Co1 115.21(12) . . ?
O3 N4 O1 122.69(15) . . ?
O3 N4 O2 121.38(15) . . ?
O1 N4 O2 115.92(14) . . ?
O6 N5 O4 122.03(15) . . ?
O6 N5 O5 121.89(15) . . ?
O4 N5 O5 116.07(14) . . ?
N4 O1 Co1 92.93(10) . . ?
N4 O2 Co1 94.75(10) . . ?
N5 O4 Co1 91.03(10) . . ?
N5 O5 Co1 95.24(10) . . ?
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
C1 N1 1.350(2) . ?
C1 C2 1.378(3) . ?
C1 H1 0.96(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.96(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.390(3) . ?
C4 H4 0.94(2) . ?
C5 N1 1.346(2) . ?
C5 C6 1.500(3) . ?
C6 C7 1.515(3) . ?
C6 H6A 0.98(2) . ?
C6 H6B 0.95(2) . ?
C7 N2 1.478(2) . ?
C7 H7A 0.92(2) . ?
C7 H7B 0.97(2) . ?
C8 N2 1.473(2) . ?
C8 C9 1.508(3) . ?
C8 H8A 1.00(2) . ?
C8 H8B 0.98(2) . ?
C9 C10 1.500(2) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.98(3) . ?
C10 N3 1.346(2) . ?
C10 C11 1.392(3) . ?
C11 C12 1.374(3) . ?
C11 H11 0.93(2) . ?
C12 C13 1.383(3) . ?
C12 H12 0.95(2) . ?
C13 C14 1.374(3) . ?
C13 H13 0.94(2) . ?
C14 N3 1.349(2) . ?
C14 H14 0.92(2) . ?
Co1 N2 2.0984(15) . ?
Co1 N1 2.1324(15) . ?
Co1 N3 2.1376(15) . ?
Co1 O5 2.1922(13) . ?
Co1 O2 2.2446(14) . ?
Co1 O1 2.2849(14) . ?
Co1 O4 2.2858(14) . ?
N4 O3 1.233(2) . ?
N4 O1 1.259(2) . ?
N4 O2 1.262(2) . ?
N5 O6 1.223(2) . ?
N5 O4 1.2623(19) . ?
N5 O5 1.268(2) . ?
