#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:29:17 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179113 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/75/4307510.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_4307510
loop_
_publ_author_name
'Martin Bröring'
'Serguei Prikhodovski'
'Carsten D. Brandt'
'Esther Cónsul Tejero'
'Silke Köhler'
'Clemens Pietzonka'
_publ_section_title
;
Cyanide-Promoted Demetalation of TrpyNiNCO: A Route to Sensitive
Metallotripyrrins of CoII, FeII, and MnII
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              917
_journal_page_last               925
_journal_paper_doi               10.1021/ic062009t
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C27 H34 Co N4 S'
_chemical_formula_weight         505.57
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.24(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.972(3)
_cell_length_b                   11.257(2)
_cell_length_c                   20.908(8)
_cell_measurement_reflns_used    6464
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2
_cell_volume                     2555.7(13)
_computing_cell_refinement       'STOE Wincell (X-Area)'
_computing_data_collection       'STOE WinXpose (X-Area)'
_computing_data_reduction        'STOE WinIntegrate (X-Area)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  IPDS1(Stoe)
_diffrn_measurement_method       'phi 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  0.1274
_diffrn_reflns_av_sigmaI/netI    0.1545
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19737
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0457
_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)+(0.0243P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2441
_reflns_number_total             4966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062009tsi20061019_115859_3.cif
_cod_data_source_block           sp5sk
_cod_database_code               4307510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.5817(4) 0.2040(3) 0.10180(17) 0.0333(10) Uani 1 1 d . . .
H1A H 0.5623 0.2764 0.1243 0.050 Uiso 1 1 calc R . .
H1B H 0.6701 0.1874 0.1117 0.050 Uiso 1 1 calc R . .
H1C H 0.5350 0.1372 0.1160 0.050 Uiso 1 1 calc R . .
C2 C 0.5479(3) 0.2207(3) 0.03101(16) 0.0237(8) Uani 1 1 d . . .
C3 C 0.6085(3) 0.2981(3) -0.00980(17) 0.0247(8) Uani 1 1 d . . .
C4 C 0.5450(3) 0.2869(3) -0.07129(16) 0.0236(8) Uani 1 1 d . . .
C5 C 0.4465(3) 0.2024(3) -0.06778(16) 0.0244(8) Uani 1 1 d . . .
C6 C 0.3625(3) 0.1635(3) -0.11800(16) 0.0224(8) Uani 1 1 d . . .
H6 H 0.3709 0.1949 -0.1593 0.027 Uiso 1 1 calc R . .
C7 C 0.2646(3) 0.0824(3) -0.11635(15) 0.0226(7) Uani 1 1 d . . .
C8 C 0.1882(3) 0.0288(3) -0.17015(16) 0.0225(8) Uani 1 1 d . . .
C9 C 0.1079(3) -0.0468(3) -0.14372(16) 0.0234(8) Uani 1 1 d . . .
C10 C 0.1388(3) -0.0378(3) -0.07485(16) 0.0216(8) Uani 1 1 d . . .
C11 C 0.0922(3) -0.1083(3) -0.02763(16) 0.0230(8) Uani 1 1 d . . .
H11 H 0.0224 -0.1559 -0.0427 0.028 Uiso 1 1 calc R . .
C12 C 0.1358(3) -0.1163(3) 0.03733(15) 0.0226(8) Uani 1 1 d . . .
C13 C 0.0946(3) -0.1972(3) 0.08314(17) 0.0236(8) Uani 1 1 d . . .
C14 C 0.1688(4) -0.1789(3) 0.14145(18) 0.0285(9) Uani 1 1 d . . .
C15 C 0.2509(3) -0.0840(3) 0.13110(15) 0.0268(8) Uani 1 1 d . . .
C16 C 0.3447(4) -0.0278(3) 0.18001(18) 0.0380(10) Uani 1 1 d . . .
H16A H 0.4271 -0.0533 0.1729 0.057 Uiso 1 1 calc R . .
H16B H 0.3305 -0.0518 0.2234 0.057 Uiso 1 1 calc R . .
H16C H 0.3385 0.0588 0.1761 0.057 Uiso 1 1 calc R . .
C17 C 0.7171(3) 0.3759(3) 0.01263(18) 0.0309(9) Uani 1 1 d . . .
H17A H 0.7645 0.3884 -0.0237 0.037 Uiso 1 1 calc R . .
H17B H 0.7715 0.3346 0.0475 0.037 Uiso 1 1 calc R . .
C18 C 0.6816(4) 0.4962(4) 0.0374(2) 0.0493(12) Uani 1 1 d . . .
H18A H 0.6248 0.5363 0.0038 0.074 Uiso 1 1 calc R . .
H18B H 0.7557 0.5448 0.0485 0.074 Uiso 1 1 calc R . .
H18C H 0.6414 0.4851 0.0759 0.074 Uiso 1 1 calc R . .
C19 C 0.5665(4) 0.3523(3) -0.13058(17) 0.0329(9) Uani 1 1 d . . .
H19A H 0.4964 0.4047 -0.1445 0.049 Uiso 1 1 calc R . .
H19B H 0.5755 0.2954 -0.1650 0.049 Uiso 1 1 calc R . .
H19C H 0.6418 0.3998 -0.1212 0.049 Uiso 1 1 calc R . .
C20 C 0.2006(4) 0.0439(3) -0.24016(17) 0.0303(9) Uani 1 1 d . . .
H20A H 0.2160 0.1288 -0.2484 0.036 Uiso 1 1 calc R . .
H20B H 0.1216 0.0218 -0.2666 0.036 Uiso 1 1 calc R . .
C21 C 0.3036(4) -0.0301(4) -0.26219(19) 0.0426(11) Uani 1 1 d . . .
H21A H 0.3827 -0.0070 -0.2374 0.064 Uiso 1 1 calc R . .
H21B H 0.3058 -0.0162 -0.3083 0.064 Uiso 1 1 calc R . .
H21C H 0.2884 -0.1145 -0.2550 0.064 Uiso 1 1 calc R . .
C22 C 0.0121(3) -0.1265(3) -0.17923(17) 0.0296(9) Uani 1 1 d . . .
H22A H -0.0256 -0.0865 -0.2194 0.036 Uiso 1 1 calc R . .
H22B H -0.0535 -0.1403 -0.1521 0.036 Uiso 1 1 calc R . .
C23 C 0.0643(4) -0.2448(3) -0.1963(2) 0.0421(11) Uani 1 1 d . . .
H23A H 0.1275 -0.2319 -0.2243 0.063 Uiso 1 1 calc R . .
H23B H -0.0018 -0.2941 -0.2189 0.063 Uiso 1 1 calc R . .
H23C H 0.1011 -0.2852 -0.1566 0.063 Uiso 1 1 calc R . .
C24 C -0.0076(4) -0.2842(3) 0.06934(19) 0.0345(10) Uani 1 1 d . . .
H24A H -0.0047 -0.3401 0.1055 0.052 Uiso 1 1 calc R . .
H24B H 0.0010 -0.3279 0.0297 0.052 Uiso 1 1 calc R . .
H24C H -0.0865 -0.2420 0.0638 0.052 Uiso 1 1 calc R . .
C25 C 0.1691(4) -0.2457(3) 0.20402(18) 0.0345(10) Uani 1 1 d . . .
H25A H 0.1515 -0.3305 0.1941 0.041 Uiso 1 1 calc R . .
H25B H 0.2523 -0.2407 0.2293 0.041 Uiso 1 1 calc R . .
C26 C 0.0770(5) -0.2001(5) 0.2446(2) 0.0612(14) Uani 1 1 d . . .
H26A H 0.0954 -0.1170 0.2561 0.092 Uiso 1 1 calc R . .
H26B H 0.0816 -0.2478 0.2841 0.092 Uiso 1 1 calc R . .
H26C H -0.0059 -0.2059 0.2202 0.092 Uiso 1 1 calc R . .
C27 C 0.2076(4) 0.3143(3) 0.09649(18) 0.0319(9) Uani 1 1 d . . .
N1 N 0.4518(3) 0.1635(2) -0.00246(13) 0.0240(7) Uani 1 1 d . . .
N2 N 0.2322(3) 0.0417(2) -0.05934(13) 0.0235(7) Uani 1 1 d . . .
N3 N 0.2344(3) -0.0468(2) 0.06961(13) 0.0254(7) Uani 1 1 d . . .
N4 N 0.2455(3) 0.2267(3) 0.07545(15) 0.0353(8) Uani 1 1 d . . .
Co Co 0.30318(5) 0.09266(4) 0.02807(2) 0.02392(14) Uani 1 1 d . . .
S S 0.15264(14) 0.43038(10) 0.12488(7) 0.0660(4) 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'
S S 0.1246 0.1234 '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 C2 C3 112.0(3) . . ?
N1 C2 C1 121.6(3) . . ?
C3 C2 C1 126.5(3) . . ?
C4 C3 C2 106.4(3) . . ?
C4 C3 C17 128.2(3) . . ?
C2 C3 C17 125.4(3) . . ?
C3 C4 C5 107.1(3) . . ?
C3 C4 C19 127.7(3) . . ?
C5 C4 C19 125.1(3) . . ?
C6 C5 N1 124.6(3) . . ?
C6 C5 C4 126.7(3) . . ?
N1 C5 C4 108.7(3) . . ?
C5 C6 C7 128.3(3) . . ?
N2 C7 C6 122.0(3) . . ?
N2 C7 C8 110.2(3) . . ?
C6 C7 C8 127.8(3) . . ?
C9 C8 C7 106.1(3) . . ?
C9 C8 C20 127.4(3) . . ?
C7 C8 C20 126.3(3) . . ?
C8 C9 C10 106.5(3) . . ?
C8 C9 C22 127.4(3) . . ?
C10 C9 C22 126.0(3) . . ?
N2 C10 C11 122.4(3) . . ?
N2 C10 C9 110.2(3) . . ?
C11 C10 C9 127.0(3) . . ?
C12 C11 C10 127.9(3) . . ?
C11 C12 N3 124.4(3) . . ?
C11 C12 C13 126.8(3) . . ?
N3 C12 C13 108.7(3) . . ?
C14 C13 C12 107.0(3) . . ?
C14 C13 C24 127.1(3) . . ?
C12 C13 C24 126.0(3) . . ?
C13 C14 C15 106.3(3) . . ?
C13 C14 C25 128.2(3) . . ?
C15 C14 C25 125.4(3) . . ?
N3 C15 C14 112.1(3) . . ?
N3 C15 C16 120.9(3) . . ?
C14 C15 C16 127.0(3) . . ?
C3 C17 C18 113.4(3) . . ?
C8 C20 C21 114.1(3) . . ?
C9 C22 C23 112.5(3) . . ?
C26 C25 C14 113.8(3) . . ?
N4 C27 S 178.3(4) . . ?
C2 N1 C5 105.8(3) . . ?
C2 N1 Co 129.8(2) . . ?
C5 N1 Co 120.3(2) . . ?
C10 N2 C7 107.0(3) . . ?
C10 N2 Co 126.6(2) . . ?
C7 N2 Co 126.4(2) . . ?
C15 N3 C12 105.8(3) . . ?
C15 N3 Co 131.0(3) . . ?
C12 N3 Co 122.3(2) . . ?
C27 N4 Co 171.5(3) . . ?
N4 Co N2 125.52(13) . . ?
N4 Co N3 102.49(11) . . ?
N2 Co N3 92.91(12) . . ?
N4 Co N1 101.05(13) . . ?
N2 Co N1 93.00(12) . . ?
N3 Co N1 146.03(12) . . ?
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 C2 1.485(5) . ?
C2 N1 1.344(5) . ?
C2 C3 1.446(5) . ?
C3 C4 1.377(5) . ?
C3 C17 1.499(5) . ?
C4 C5 1.449(5) . ?
C4 C19 1.490(5) . ?
C5 C6 1.366(5) . ?
C5 N1 1.427(4) . ?
C6 C7 1.414(5) . ?
C7 N2 1.371(4) . ?
C7 C8 1.436(5) . ?
C8 C9 1.394(5) . ?
C8 C20 1.499(5) . ?
C9 C10 1.435(5) . ?
C9 C22 1.495(5) . ?
C10 N2 1.364(4) . ?
C10 C11 1.418(5) . ?
C11 C12 1.377(5) . ?
C12 N3 1.425(4) . ?
C12 C13 1.441(5) . ?
C13 C14 1.381(5) . ?
C13 C24 1.486(5) . ?
C14 C15 1.434(5) . ?
C14 C25 1.508(5) . ?
C15 N3 1.339(4) . ?
C15 C16 1.484(5) . ?
C17 C18 1.520(5) . ?
C20 C21 1.527(5) . ?
C22 C23 1.513(5) . ?
C25 C26 1.500(6) . ?
C27 N4 1.179(4) . ?
C27 S 1.590(4) . ?
N1 Co 2.000(3) . ?
N2 Co 1.967(3) . ?
N3 Co 1.994(3) . ?
N4 Co 1.959(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
N1 C2 C3 C17 178.8(3) . . . . ?
C1 C2 C3 C17 -0.1(6) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C17 C3 C4 C5 -179.0(3) . . . . ?
C2 C3 C4 C19 176.8(3) . . . . ?
C17 C3 C4 C19 -1.9(6) . . . . ?
C3 C4 C5 C6 -178.7(3) . . . . ?
C19 C4 C5 C6 4.2(6) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C19 C4 C5 N1 -176.8(3) . . . . ?
N1 C5 C6 C7 1.9(6) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C5 C6 C7 N2 8.3(6) . . . . ?
C5 C6 C7 C8 -170.0(4) . . . . ?
N2 C7 C8 C9 -0.2(4) . . . . ?
C6 C7 C8 C9 178.2(3) . . . . ?
N2 C7 C8 C20 -175.4(3) . . . . ?
C6 C7 C8 C20 3.0(6) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C20 C8 C9 C10 174.6(3) . . . . ?
C7 C8 C9 C22 -178.0(3) . . . . ?
C20 C8 C9 C22 -2.8(6) . . . . ?
C8 C9 C10 N2 1.3(4) . . . . ?
C22 C9 C10 N2 178.7(3) . . . . ?
C8 C9 C10 C11 -172.1(3) . . . . ?
C22 C9 C10 C11 5.3(6) . . . . ?
N2 C10 C11 C12 -5.4(5) . . . . ?
C9 C10 C11 C12 167.2(3) . . . . ?
C10 C11 C12 N3 4.0(6) . . . . ?
C10 C11 C12 C13 -173.3(3) . . . . ?
C11 C12 C13 C14 176.3(3) . . . . ?
N3 C12 C13 C14 -1.3(4) . . . . ?
C11 C12 C13 C24 -3.2(6) . . . . ?
N3 C12 C13 C24 179.2(3) . . . . ?
C12 C13 C14 C15 2.2(4) . . . . ?
C24 C13 C14 C15 -178.3(3) . . . . ?
C12 C13 C14 C25 -176.1(3) . . . . ?
C24 C13 C14 C25 3.4(6) . . . . ?
C13 C14 C15 N3 -2.4(4) . . . . ?
C25 C14 C15 N3 175.9(3) . . . . ?
C13 C14 C15 C16 177.0(4) . . . . ?
C25 C14 C15 C16 -4.7(6) . . . . ?
C4 C3 C17 C18 92.7(5) . . . . ?
C2 C3 C17 C18 -85.7(5) . . . . ?
C9 C8 C20 C21 -96.0(4) . . . . ?
C7 C8 C20 C21 78.2(5) . . . . ?
C8 C9 C22 C23 84.5(5) . . . . ?
C10 C9 C22 C23 -92.3(4) . . . . ?
C13 C14 C25 C26 -85.4(5) . . . . ?
C15 C14 C25 C26 96.6(5) . . . . ?
C3 C2 N1 C5 0.1(4) . . . . ?
C1 C2 N1 C5 179.1(3) . . . . ?
C3 C2 N1 Co -156.5(2) . . . . ?
C1 C2 N1 Co 22.5(5) . . . . ?
C6 C5 N1 C2 178.8(3) . . . . ?
C4 C5 N1 C2 -0.3(4) . . . . ?
C6 C5 N1 Co -21.9(4) . . . . ?
C4 C5 N1 Co 159.0(2) . . . . ?
C11 C10 N2 C7 172.3(3) . . . . ?
C9 C10 N2 C7 -1.4(4) . . . . ?
C11 C10 N2 Co -9.6(5) . . . . ?
C9 C10 N2 Co 176.7(2) . . . . ?
C6 C7 N2 C10 -177.6(3) . . . . ?
C8 C7 N2 C10 1.0(4) . . . . ?
C6 C7 N2 Co 4.4(5) . . . . ?
C8 C7 N2 Co -177.1(2) . . . . ?
C14 C15 N3 C12 1.6(4) . . . . ?
C16 C15 N3 C12 -177.9(3) . . . . ?
C14 C15 N3 Co 171.1(3) . . . . ?
C16 C15 N3 Co -8.3(5) . . . . ?
C11 C12 N3 C15 -177.9(3) . . . . ?
C13 C12 N3 C15 -0.1(4) . . . . ?
C11 C12 N3 Co 11.4(4) . . . . ?
C13 C12 N3 Co -170.8(2) . . . . ?
S C27 N4 Co 99(12) . . . . ?
C27 N4 Co N2 -35(2) . . . . ?
C27 N4 Co N3 -138(2) . . . . ?
C27 N4 Co N1 67(2) . . . . ?
C10 N2 Co N4 -89.4(3) . . . . ?
C7 N2 Co N4 88.3(3) . . . . ?
C10 N2 Co N3 18.2(3) . . . . ?
C7 N2 Co N3 -164.1(3) . . . . ?
C10 N2 Co N1 164.8(3) . . . . ?
C7 N2 Co N1 -17.6(3) . . . . ?
C15 N3 Co N4 -59.1(3) . . . . ?
C12 N3 Co N4 109.0(3) . . . . ?
C15 N3 Co N2 173.5(3) . . . . ?
C12 N3 Co N2 -18.4(3) . . . . ?
C15 N3 Co N1 73.7(4) . . . . ?
C12 N3 Co N1 -118.2(3) . . . . ?
C2 N1 Co N4 51.5(3) . . . . ?
C5 N1 Co N4 -102.2(2) . . . . ?
C2 N1 Co N2 178.6(3) . . . . ?
C5 N1 Co N2 24.9(2) . . . . ?
C2 N1 Co N3 -81.7(4) . . . . ?
C5 N1 Co N3 124.6(3) . . . . ?
