#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:47:32 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179306 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/03/4320380.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_4320380
loop_
_publ_author_name
'James A. Johnson'
'Marilyn M. Olmstead'
'Alan M. Stolzenberg'
'Alan L. Balch'
_publ_section_title
;
 Ring-Opening and Meso Substitution from the Reaction of Cyanide Ion with
 Zinc Verdohemes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5585
_journal_page_last               5595
_journal_paper_doi               10.1021/ic0103300
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C40 H48 Co N6 O2'
_chemical_formula_weight         703.77
_chemical_name_common            '[CoOEB-15,19-(CN)2].acetone'
_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                96.780(4)
_cell_angle_beta                 96.299(4)
_cell_angle_gamma                104.384(4)
_cell_formula_units_Z            2
_cell_length_a                   11.465(3)
_cell_length_b                   12.133(3)
_cell_length_c                   13.833(3)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      2.2
_cell_volume                     1831.4(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 5, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23884
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_correction_T_min  0.7805
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2 (Sheldrick, 2000)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             746
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0002(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0518
_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)+(0.0748P)²+1.0009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                4841
_reflns_number_total             6631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0103300_3.cif
_cod_data_source_block           mn1117
_cod_original_cell_volume        1831.5(8)
_cod_database_code               4320380
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 0.23429(4) 0.30120(4) 0.34987(3) 0.01604(15) Uani 1 1 d . . .
O1 O 0.1041(2) 0.1406(2) 0.14621(17) 0.0278(6) Uani 1 1 d . . .
N1 N 0.0952(2) 0.1799(2) 0.31485(19) 0.0186(6) Uani 1 1 d . . .
N2 N 0.1790(2) 0.3497(2) 0.46667(19) 0.0167(6) Uani 1 1 d . . .
N3 N 0.3593(2) 0.4365(2) 0.35949(19) 0.0154(6) Uani 1 1 d . . .
N4 N 0.3315(2) 0.2181(2) 0.28761(19) 0.0167(6) Uani 1 1 d . . .
N5 N 0.2211(3) -0.0202(2) 0.4061(2) 0.0272(7) Uani 1 1 d . . .
N6 N 0.5739(3) 0.4348(3) 0.0779(2) 0.0271(7) Uani 1 1 d . . .
C1 C 0.0612(3) 0.1129(3) 0.2188(2) 0.0240(8) Uani 1 1 d . . .
C2 C -0.0393(3) 0.0102(3) 0.2248(3) 0.0291(8) Uani 1 1 d . . .
C3 C -0.0715(3) 0.0253(3) 0.3148(2) 0.0233(7) Uani 1 1 d . . .
C4 C 0.0134(3) 0.1320(3) 0.3712(2) 0.0185(7) Uani 1 1 d . . .
C5 C 0.0115(3) 0.1794(3) 0.4669(2) 0.0177(7) Uani 1 1 d . . .
H5 H -0.0443 0.1380 0.5043 0.021 Uiso 1 1 calc R . .
C6 C 0.0888(3) 0.2864(3) 0.5106(2) 0.0154(6) Uani 1 1 d . . .
C7 C 0.0831(3) 0.3495(3) 0.6053(2) 0.0175(7) Uani 1 1 d . . .
C8 C 0.1679(3) 0.4529(3) 0.6160(2) 0.0172(7) Uani 1 1 d . . .
C9 C 0.2301(3) 0.4529(3) 0.5297(2) 0.0154(6) Uani 1 1 d . . .
C10 C 0.3244(3) 0.5387(3) 0.5106(2) 0.0179(7) Uani 1 1 d . . .
H10 H 0.3515 0.6070 0.5574 0.021 Uiso 1 1 calc R . .
C11 C 0.3832(3) 0.5332(3) 0.4276(2) 0.0176(7) Uani 1 1 d . . .
C12 C 0.4776(3) 0.6238(3) 0.4011(2) 0.0166(7) Uani 1 1 d . . .
C13 C 0.5086(3) 0.5815(3) 0.3138(2) 0.0173(7) Uani 1 1 d . . .
C14 C 0.4365(3) 0.4616(3) 0.2894(2) 0.0166(7) Uani 1 1 d . . .
C15 C 0.4463(3) 0.3752(3) 0.2163(2) 0.0168(7) Uani 1 1 d . . .
C16 C 0.3986(3) 0.2546(3) 0.2158(2) 0.0159(6) Uani 1 1 d . . .
C17 C 0.4237(3) 0.1582(3) 0.1596(2) 0.0165(7) Uani 1 1 d . . .
C18 C 0.3746(3) 0.0625(3) 0.2037(2) 0.0179(7) Uani 1 1 d . . .
C19 C 0.3190(3) 0.1019(3) 0.2810(2) 0.0172(7) Uani 1 1 d . . .
C20 C 0.2623(3) 0.0363(3) 0.3509(2) 0.0199(7) Uani 1 1 d . . .
C21 C -0.0920(4) -0.0838(3) 0.1378(3) 0.0355(9) Uani 1 1 d . . .
H21A H -0.0260 -0.0960 0.1007 0.043 Uiso 1 1 calc R . .
H21B H -0.1284 -0.1566 0.1616 0.043 Uiso 1 1 calc R . .
C22 C -0.1863(4) -0.0536(4) 0.0713(3) 0.0449(11) Uani 1 1 d . . .
H22A H -0.2544 -0.0469 0.1066 0.067 Uiso 1 1 calc R . .
H22B H -0.2156 -0.1140 0.0139 0.067 Uiso 1 1 calc R . .
H22C H -0.1511 0.0199 0.0495 0.067 Uiso 1 1 calc R . .
C23 C -0.1762(3) -0.0458(3) 0.3553(3) 0.0292(8) Uani 1 1 d . . .
H23A H -0.1505 -0.0497 0.4252 0.035 Uiso 1 1 calc R . .
H23B H -0.1997 -0.1251 0.3189 0.035 Uiso 1 1 calc R . .
C24 C -0.2863(4) 0.0043(4) 0.3473(3) 0.0381(10) Uani 1 1 d . . .
H24A H -0.2623 0.0842 0.3804 0.057 Uiso 1 1 calc R . .
H24B H -0.3507 -0.0412 0.3786 0.057 Uiso 1 1 calc R . .
H24C H -0.3164 0.0019 0.2778 0.057 Uiso 1 1 calc R . .
C25 C -0.0055(3) 0.3076(3) 0.6742(2) 0.0212(7) Uani 1 1 d . . .
H25A H 0.0337 0.3373 0.7429 0.025 Uiso 1 1 calc R . .
H25B H -0.0264 0.2225 0.6659 0.025 Uiso 1 1 calc R . .
C26 C -0.1217(4) 0.3459(4) 0.6560(3) 0.0391(10) Uani 1 1 d . . .
H26A H -0.1018 0.4301 0.6667 0.059 Uiso 1 1 calc R . .
H26B H -0.1771 0.3155 0.7014 0.059 Uiso 1 1 calc R . .
H26C H -0.1609 0.3166 0.5880 0.059 Uiso 1 1 calc R . .
C27 C 0.1940(3) 0.5534(3) 0.6973(2) 0.0195(7) Uani 1 1 d . . .
H27A H 0.2831 0.5873 0.7129 0.023 Uiso 1 1 calc R . .
H27B H 0.1644 0.5261 0.7571 0.023 Uiso 1 1 calc R . .
C28 C 0.1324(3) 0.6463(3) 0.6682(3) 0.0262(8) Uani 1 1 d . . .
H28A H 0.1629 0.6746 0.6098 0.039 Uiso 1 1 calc R . .
H28B H 0.1510 0.7103 0.7227 0.039 Uiso 1 1 calc R . .
H28C H 0.0441 0.6132 0.6537 0.039 Uiso 1 1 calc R . .
C29 C 0.5293(3) 0.7398(3) 0.4631(2) 0.0209(7) Uani 1 1 d . . .
H29A H 0.6077 0.7770 0.4423 0.025 Uiso 1 1 calc R . .
H29B H 0.5465 0.7288 0.5325 0.025 Uiso 1 1 calc R . .
C30 C 0.4465(3) 0.8211(3) 0.4575(3) 0.0288(8) Uani 1 1 d . . .
H30A H 0.4292 0.8331 0.3891 0.043 Uiso 1 1 calc R . .
H30B H 0.4872 0.8951 0.4985 0.043 Uiso 1 1 calc R . .
H30C H 0.3701 0.7870 0.4811 0.043 Uiso 1 1 calc R . .
C31 C 0.6021(3) 0.6466(3) 0.2588(2) 0.0215(7) Uani 1 1 d . . .
H31A H 0.6474 0.5939 0.2309 0.026 Uiso 1 1 calc R . .
H31B H 0.6608 0.7090 0.3056 0.026 Uiso 1 1 calc R . .
C32 C 0.5470(4) 0.6991(3) 0.1756(3) 0.0292(8) Uani 1 1 d . . .
H32A H 0.4904 0.6377 0.1279 0.044 Uiso 1 1 calc R . .
H32B H 0.6122 0.7407 0.1427 0.044 Uiso 1 1 calc R . .
H32C H 0.5033 0.7526 0.2028 0.044 Uiso 1 1 calc R . .
C33 C 0.5177(3) 0.4095(3) 0.1397(2) 0.0195(7) Uani 1 1 d . . .
C34 C 0.4925(3) 0.1550(3) 0.0740(2) 0.0200(7) Uani 1 1 d . . .
H34A H 0.4792 0.2148 0.0345 0.024 Uiso 1 1 calc R . .
H34B H 0.4599 0.0793 0.0317 0.024 Uiso 1 1 calc R . .
C35 C 0.6291(3) 0.1745(3) 0.1047(3) 0.0262(8) Uani 1 1 d . . .
H35A H 0.6626 0.2504 0.1449 0.039 Uiso 1 1 calc R . .
H35B H 0.6693 0.1709 0.0459 0.039 Uiso 1 1 calc R . .
H35C H 0.6431 0.1148 0.1430 0.039 Uiso 1 1 calc R . .
C36 C 0.3780(3) -0.0603(3) 0.1779(2) 0.0224(7) Uani 1 1 d . . .
H36A H 0.4172 -0.0845 0.2362 0.027 Uiso 1 1 calc R . .
H36B H 0.4288 -0.0650 0.1249 0.027 Uiso 1 1 calc R . .
C37 C 0.2527(3) -0.1436(3) 0.1441(3) 0.0287(8) Uani 1 1 d . . .
H37A H 0.2038 -0.1441 0.1979 0.043 Uiso 1 1 calc R . .
H37B H 0.2616 -0.2212 0.1251 0.043 Uiso 1 1 calc R . .
H37C H 0.2122 -0.1191 0.0875 0.043 Uiso 1 1 calc R . .
O2 O 0.0232(4) 0.3791(4) -0.0750(3) 0.0799(12) Uani 1 1 d . . .
C38 C 0.0582(5) 0.3795(4) 0.0114(4) 0.0519(12) Uani 1 1 d . . .
C39 C 0.1896(5) 0.4094(7) 0.0540(6) 0.101(3) Uani 1 1 d . . .
H39A H 0.2051 0.3483 0.0899 0.151 Uiso 1 1 calc R . .
H39B H 0.2103 0.4823 0.0992 0.151 Uiso 1 1 calc R . .
H39C H 0.2397 0.4174 0.0008 0.151 Uiso 1 1 calc R . .
C40 C -0.0301(5) 0.3516(5) 0.0799(4) 0.0637(15) Uani 1 1 d . . .
H40A H -0.1118 0.3468 0.0470 0.096 Uiso 1 1 calc R . .
H40B H -0.0089 0.4118 0.1375 0.096 Uiso 1 1 calc R . .
H40C H -0.0285 0.2775 0.1008 0.096 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'
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
N1 Co1 N3 166.45(11) . . ?
N1 Co1 N2 91.21(12) . . ?
N3 Co1 N2 94.01(11) . . ?
N1 Co1 N4 92.73(12) . . ?
N3 Co1 N4 89.44(11) . . ?
N2 Co1 N4 148.12(11) . . ?
C4 N1 C1 106.9(3) . . ?
C4 N1 Co1 129.4(2) . . ?
C1 N1 Co1 123.5(2) . . ?
C6 N2 C9 106.9(3) . . ?
C6 N2 Co1 126.8(2) . . ?
C9 N2 Co1 126.1(2) . . ?
C11 N3 C14 107.0(3) . . ?
C11 N3 Co1 127.7(2) . . ?
C14 N3 Co1 124.9(2) . . ?
C16 N4 C19 106.3(3) . . ?
C16 N4 Co1 124.3(2) . . ?
C19 N4 Co1 126.4(2) . . ?
O1 C1 N1 124.6(3) . . ?
O1 C1 C2 127.6(3) . . ?
N1 C1 C2 107.7(3) . . ?
C3 C2 C1 106.9(3) . . ?
C3 C2 C21 131.1(3) . . ?
C1 C2 C21 121.9(3) . . ?
C2 C3 C4 108.0(3) . . ?
C2 C3 C23 128.8(3) . . ?
C4 C3 C23 123.2(3) . . ?
N1 C4 C5 123.3(3) . . ?
N1 C4 C3 110.0(3) . . ?
C5 C4 C3 126.8(3) . . ?
C4 C5 C6 122.3(3) . . ?
N2 C6 C5 123.9(3) . . ?
N2 C6 C7 109.8(3) . . ?
C5 C6 C7 126.2(3) . . ?
C8 C7 C6 107.1(3) . . ?
C8 C7 C25 127.9(3) . . ?
C6 C7 C25 125.0(3) . . ?
C7 C8 C9 107.1(3) . . ?
C7 C8 C27 128.9(3) . . ?
C9 C8 C27 123.9(3) . . ?
C10 C9 N2 123.8(3) . . ?
C10 C9 C8 127.2(3) . . ?
N2 C9 C8 109.0(3) . . ?
C9 C10 C11 124.9(3) . . ?
N3 C11 C10 123.0(3) . . ?
N3 C11 C12 110.0(3) . . ?
C10 C11 C12 127.0(3) . . ?
C13 C12 C11 107.5(3) . . ?
C13 C12 C29 129.0(3) . . ?
C11 C12 C29 123.6(3) . . ?
C12 C13 C14 106.1(3) . . ?
C12 C13 C31 125.6(3) . . ?
C14 C13 C31 128.2(3) . . ?
N3 C14 C15 121.1(3) . . ?
N3 C14 C13 109.3(3) . . ?
C15 C14 C13 129.2(3) . . ?
C14 C15 C16 124.8(3) . . ?
C14 C15 C33 118.0(3) . . ?
C16 C15 C33 117.1(3) . . ?
N4 C16 C15 119.1(3) . . ?
N4 C16 C17 109.8(3) . . ?
C15 C16 C17 130.3(3) . . ?
C18 C17 C16 106.0(3) . . ?
C18 C17 C34 124.5(3) . . ?
C16 C17 C34 129.4(3) . . ?
C17 C18 C19 106.6(3) . . ?
C17 C18 C36 129.2(3) . . ?
C19 C18 C36 124.2(3) . . ?
N4 C19 C18 111.1(3) . . ?
N4 C19 C20 121.7(3) . . ?
C18 C19 C20 127.1(3) . . ?
N5 C20 C19 176.2(3) . . ?
C22 C21 C2 111.2(3) . . ?
C3 C23 C24 111.8(3) . . ?
C7 C25 C26 112.3(3) . . ?
C8 C27 C28 111.5(3) . . ?
C12 C29 C30 114.4(3) . . ?
C13 C31 C32 113.2(3) . . ?
N6 C33 C15 178.8(4) . . ?
C17 C34 C35 113.0(3) . . ?
C18 C36 C37 113.6(3) . . ?
O2 C38 C40 120.1(5) . . ?
O2 C38 C39 123.3(5) . . ?
C40 C38 C39 116.6(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 N1 1.854(3) . ?
Co1 N3 1.872(3) . ?
Co1 N2 1.882(3) . ?
Co1 N4 1.888(3) . ?
O1 C1 1.212(4) . ?
N1 C4 1.350(4) . ?
N1 C1 1.432(4) . ?
N2 C6 1.372(4) . ?
N2 C9 1.392(4) . ?
N3 C11 1.365(4) . ?
N3 C14 1.392(4) . ?
N4 C16 1.370(4) . ?
N4 C19 1.372(4) . ?
N5 C20 1.149(4) . ?
N6 C33 1.151(4) . ?
C1 C2 1.490(5) . ?
C2 C3 1.342(5) . ?
C2 C21 1.513(5) . ?
C3 C4 1.484(5) . ?
C3 C23 1.498(5) . ?
C4 C5 1.385(4) . ?
C5 C6 1.400(4) . ?
C6 C7 1.453(4) . ?
C7 C8 1.364(5) . ?
C7 C25 1.507(4) . ?
C8 C9 1.456(4) . ?
C8 C27 1.503(4) . ?
C9 C10 1.375(4) . ?
C10 C11 1.397(5) . ?
C11 C12 1.451(4) . ?
C12 C13 1.373(5) . ?
C12 C29 1.503(4) . ?
C13 C14 1.463(4) . ?
C13 C31 1.500(4) . ?
C14 C15 1.402(4) . ?
C15 C16 1.428(4) . ?
C15 C33 1.447(4) . ?
C16 C17 1.435(4) . ?
C17 C18 1.398(4) . ?
C17 C34 1.495(4) . ?
C18 C19 1.400(4) . ?
C18 C36 1.502(4) . ?
C19 C20 1.433(4) . ?
C21 C22 1.486(6) . ?
C23 C24 1.530(6) . ?
C25 C26 1.521(5) . ?
C27 C28 1.540(4) . ?
C29 C30 1.532(5) . ?
C31 C32 1.531(5) . ?
C34 C35 1.529(5) . ?
C36 C37 1.524(5) . ?
O2 C38 1.218(6) . ?
C38 C40 1.467(7) . ?
C38 C39 1.494(7) . ?
