#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:38:45 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180149 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/46/7104657.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_7104657
loop_
_publ_author_name
'Sripothongnak, Saovalak'
'Barone, Natalie'
'Ziegler, Christopher J'
_publ_section_title
;
 C-H bond activation and ring oxidation in nickel
 carbahemiporphyrazines.
;
_journal_issue                   30
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4584
_journal_page_last               4586
_journal_paper_doi               10.1039/b909871b
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C30 H24 N6 Ni O3'
_chemical_formula_weight         575.26
_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                 104.292(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.612(2)
_cell_length_b                   7.5293(10)
_cell_length_c                   21.551(3)
_cell_measurement_reflns_used    4179
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.69
_cell_volume                     2454.9(6)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19549
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0495
_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)+(0.0520P)²+1.1927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                4141
_reflns_number_total             5514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909871b.txt
_cod_data_source_block           2ONi
_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_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7104657
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 0.14699(17) 0.2412(4) 0.06283(12) 0.0292(6) Uani 1 1 d . . .
C2 C 0.05534(18) 0.2461(4) 0.02213(13) 0.0303(6) Uani 1 1 d . . .
C3 C -0.02407(19) 0.2948(4) 0.03560(14) 0.0374(7) Uani 1 1 d . . .
H3 H -0.0263 0.3358 0.0769 0.045 Uiso 1 1 calc R . .
C4 C -0.10021(19) 0.2810(5) -0.01395(15) 0.0423(8) Uani 1 1 d . . .
H4 H -0.1553 0.3169 -0.0068 0.051 Uiso 1 1 calc R . .
C5 C -0.09719(19) 0.2158(4) -0.07362(14) 0.0396(8) Uani 1 1 d . . .
H5 H -0.1505 0.2068 -0.1063 0.047 Uiso 1 1 calc R . .
C6 C -0.01847(18) 0.1636(4) -0.08677(13) 0.0338(7) Uani 1 1 d . . .
H6 H -0.0167 0.1164 -0.1273 0.041 Uiso 1 1 calc R . .
C7 C 0.05768(17) 0.1835(4) -0.03791(13) 0.0282(6) Uani 1 1 d . . .
C8 C 0.15167(17) 0.1529(4) -0.03486(12) 0.0262(6) Uani 1 1 d . . .
C9 C 0.26743(17) 0.0744(4) -0.08893(12) 0.0262(6) Uani 1 1 d . . .
C10 C 0.27413(18) 0.0017(4) -0.14719(12) 0.0303(6) Uani 1 1 d . . .
H10 H 0.2234 -0.0470 -0.1759 0.036 Uiso 1 1 calc R . .
C11 C 0.35450(18) 0.0007(4) -0.16305(13) 0.0318(6) Uani 1 1 d . . .
H11 H 0.3601 -0.0510 -0.2021 0.038 Uiso 1 1 calc R . .
C12 C 0.42655(18) 0.0763(4) -0.12118(12) 0.0302(6) Uani 1 1 d . . .
H12 H 0.4818 0.0818 -0.1321 0.036 Uiso 1 1 calc R . .
C13 C 0.41807(16) 0.1449(4) -0.06246(12) 0.0259(6) Uani 1 1 d . . .
C14 C 0.33951(17) 0.1423(4) -0.04116(12) 0.0252(6) Uani 1 1 d . . .
C15 C 0.51213(17) 0.2870(3) 0.03222(12) 0.0264(6) Uani 1 1 d . . .
C16 C 0.59877(17) 0.3617(4) 0.06569(12) 0.0262(6) Uani 1 1 d . . .
C17 C 0.67819(18) 0.3805(4) 0.04857(13) 0.0302(6) Uani 1 1 d . . .
H17 H 0.6844 0.3449 0.0076 0.036 Uiso 1 1 calc R . .
C18 C 0.74860(18) 0.4541(4) 0.09413(13) 0.0321(6) Uani 1 1 d . . .
H18 H 0.8040 0.4695 0.0840 0.038 Uiso 1 1 calc R . .
C19 C 0.73924(18) 0.5051(4) 0.15401(13) 0.0348(7) Uani 1 1 d . . .
H19 H 0.7880 0.5571 0.1837 0.042 Uiso 1 1 calc R . .
C20 C 0.65988(18) 0.4816(4) 0.17140(13) 0.0334(7) Uani 1 1 d . . .
H20 H 0.6540 0.5146 0.2127 0.040 Uiso 1 1 calc R . .
C21 C 0.58977(17) 0.4085(4) 0.12645(12) 0.0286(6) Uani 1 1 d . . .
C22 C 0.50036(17) 0.3507(4) 0.13049(12) 0.0268(6) Uani 1 1 d . . .
C23 C 0.40312(17) 0.2702(4) 0.19576(12) 0.0281(6) Uani 1 1 d . . .
C24 C 0.40819(18) 0.1745(4) 0.25206(12) 0.0310(6) Uani 1 1 d . . .
H24 H 0.4637 0.1607 0.2820 0.037 Uiso 1 1 calc R . .
C25 C 0.33356(19) 0.0994(4) 0.26486(13) 0.0334(6) Uani 1 1 d . . .
H25 H 0.3381 0.0319 0.3028 0.040 Uiso 1 1 calc R . .
C26 C 0.25179(18) 0.1231(4) 0.22194(12) 0.0309(6) Uani 1 1 d . . .
H26 H 0.2003 0.0734 0.2310 0.037 Uiso 1 1 calc R . .
C27 C 0.24501(17) 0.2197(3) 0.16562(12) 0.0256(6) Uani 1 1 d . . .
C28 C 0.32054(17) 0.2994(4) 0.15301(12) 0.0268(6) Uani 1 1 d . . .
C29 C 0.5213(2) 0.7016(4) 0.28404(15) 0.0435(8) Uani 1 1 d . . .
H29A H 0.4719 0.7164 0.3041 0.065 Uiso 1 1 calc R . .
H29B H 0.5001 0.7167 0.2376 0.065 Uiso 1 1 calc R . .
H29C H 0.5668 0.7907 0.3010 0.065 Uiso 1 1 calc R . .
C30 C 0.33746(19) 0.8301(4) 0.12746(16) 0.0406(7) Uani 1 1 d . . .
H530 H 0.3091 0.7702 0.1575 0.061 Uiso 1 1 calc R . .
H30B H 0.2920 0.8751 0.0910 0.061 Uiso 1 1 calc R . .
H30C H 0.3732 0.9294 0.1491 0.061 Uiso 1 1 calc R . .
H2N H 0.141(2) 0.059(4) -0.1138(14) 0.036(9) Uiso 1 1 d . . .
H3N H 0.536(2) 0.236(4) -0.0439(14) 0.028(8) Uiso 1 1 d . . .
H2O H 0.540(2) 0.471(5) 0.2694(17) 0.050(11) Uiso 1 1 d . . .
H3O H 0.367(2) 0.613(5) 0.1038(17) 0.055(12) Uiso 1 1 d . . .
N1 N 0.20487(14) 0.2013(3) 0.02154(10) 0.0265(5) Uani 1 1 d . . .
N2 N 0.17956(15) 0.0866(3) -0.08306(11) 0.0282(5) Uani 1 1 d . . .
N3 N 0.49681(15) 0.2232(3) -0.02626(10) 0.0264(5) Uani 1 1 d . . .
N4 N 0.45318(14) 0.2895(3) 0.06847(10) 0.0257(5) Uani 1 1 d . . .
N5 N 0.48208(14) 0.3416(3) 0.18557(10) 0.0279(5) Uani 1 1 d . . .
N6 N 0.16113(14) 0.2430(3) 0.12387(10) 0.0274(5) Uani 1 1 d . . .
Ni1 Ni 0.32876(2) 0.24642(5) 0.037402(15) 0.02565(11) Uani 1 1 d . . .
O1 O 0.31195(12) 0.4063(3) 0.10200(8) 0.0311(4) Uani 1 1 d . . .
O2 O 0.55796(13) 0.5282(3) 0.29763(10) 0.0351(5) Uani 1 1 d . . .
O3 O 0.39178(14) 0.7095(3) 0.10565(10) 0.0374(5) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
N6 C1 N1 131.2(2) . . ?
N6 C1 C2 120.3(2) . . ?
N1 C1 C2 107.4(2) . . ?
C7 C2 C3 121.0(3) . . ?
C7 C2 C1 107.4(2) . . ?
C3 C2 C1 131.5(3) . . ?
C2 C3 C4 117.2(3) . . ?
C5 C4 C3 121.3(3) . . ?
C6 C5 C4 121.7(3) . . ?
C5 C6 C7 116.8(3) . . ?
C2 C7 C6 122.0(2) . . ?
C2 C7 C8 105.5(2) . . ?
C6 C7 C8 132.5(2) . . ?
N2 C8 N1 124.4(2) . . ?
N2 C8 C7 122.9(2) . . ?
N1 C8 C7 112.7(2) . . ?
C10 C9 N2 113.3(2) . . ?
C10 C9 C14 124.8(2) . . ?
N2 C9 C14 121.7(2) . . ?
C11 C10 C9 120.0(2) . . ?
C12 C11 C10 118.7(2) . . ?
C11 C12 C13 119.9(3) . . ?
C12 C13 N3 112.9(2) . . ?
C12 C13 C14 124.8(2) . . ?
N3 C13 C14 122.3(2) . . ?
C13 C14 C9 111.4(2) . . ?
C13 C14 Ni1 123.78(19) . . ?
C9 C14 Ni1 124.28(19) . . ?
N3 C15 N4 124.9(2) . . ?
N3 C15 C16 122.3(2) . . ?
N4 C15 C16 112.7(2) . . ?
C17 C16 C21 121.9(2) . . ?
C17 C16 C15 132.9(2) . . ?
C21 C16 C15 105.2(2) . . ?
C16 C17 C18 117.0(2) . . ?
C19 C18 C17 121.2(3) . . ?
C18 C19 C20 121.3(3) . . ?
C21 C20 C19 117.7(3) . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 C22 131.9(2) . . ?
C16 C21 C22 107.1(2) . . ?
N5 C22 N4 131.4(2) . . ?
N5 C22 C21 119.6(2) . . ?
N4 C22 C21 108.3(2) . . ?
C24 C23 C28 119.8(2) . . ?
C24 C23 N5 117.9(2) . . ?
C28 C23 N5 122.3(2) . . ?
C25 C24 C23 121.0(3) . . ?
C24 C25 C26 119.7(3) . . ?
C25 C26 C27 120.3(3) . . ?
C26 C27 N6 118.7(2) . . ?
C26 C27 C28 120.2(2) . . ?
N6 C27 C28 121.1(2) . . ?
O1 C28 C23 121.4(2) . . ?
O1 C28 C27 119.6(2) . . ?
C23 C28 C27 118.9(2) . . ?
C8 N1 C1 105.8(2) . . ?
C8 N1 Ni1 125.69(18) . . ?
C1 N1 Ni1 127.68(17) . . ?
C8 N2 C9 127.7(2) . . ?
C15 N3 C13 127.6(2) . . ?
C15 N4 C22 106.1(2) . . ?
C15 N4 Ni1 124.97(17) . . ?
C22 N4 Ni1 128.49(17) . . ?
C22 N5 C23 124.3(2) . . ?
C1 N6 C27 123.7(2) . . ?
O1 Ni1 N1 85.82(9) . . ?
O1 Ni1 C14 164.59(10) . . ?
N1 Ni1 C14 94.30(10) . . ?
O1 Ni1 N4 87.05(8) . . ?
N1 Ni1 N4 170.23(9) . . ?
C14 Ni1 N4 94.35(10) . . ?
C28 O1 Ni1 102.44(16) . . ?
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 N6 1.279(3) . ?
C1 N1 1.448(3) . ?
C1 C2 1.483(4) . ?
C2 C7 1.386(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.392(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.385(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.471(4) . ?
C8 N2 1.320(3) . ?
C8 N1 1.342(3) . ?
C9 C10 1.397(4) . ?
C9 N2 1.411(3) . ?
C9 C14 1.420(3) . ?
C10 C11 1.380(4) . ?
C11 C12 1.379(4) . ?
C12 C13 1.403(4) . ?
C13 N3 1.412(3) . ?
C13 C14 1.412(4) . ?
C14 Ni1 1.910(3) . ?
C15 N3 1.315(3) . ?
C15 N4 1.346(3) . ?
C15 C16 1.478(3) . ?
C16 C17 1.385(4) . ?
C16 C21 1.396(4) . ?
C17 C18 1.395(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.391(4) . ?
C20 C21 1.384(4) . ?
C21 C22 1.485(4) . ?
C22 N5 1.289(3) . ?
C22 N4 1.433(3) . ?
C23 C24 1.397(4) . ?
C23 C28 1.405(4) . ?
C23 N5 1.411(3) . ?
C24 C25 1.383(4) . ?
C25 C26 1.391(4) . ?
C26 C27 1.397(4) . ?
C27 N6 1.405(3) . ?
C27 C28 1.408(4) . ?
C28 O1 1.342(3) . ?
C29 O2 1.426(4) . ?
C30 O3 1.400(4) . ?
N1 Ni1 1.910(2) . ?
N4 Ni1 1.919(2) . ?
Ni1 O1 1.9070(19) . ?
