#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:38:45 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180149 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/46/7104658.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_7104658
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            'C36 H31 N9 Ni O2'
_chemical_formula_weight         680.41
_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                 133.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.375(12)
_cell_length_b                   8.708(6)
_cell_length_c                   26.492(13)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.22
_cell_volume                     3053(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1474
_diffrn_reflns_av_sigmaI/netI    0.1466
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23929
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.9040
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0787
_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)+(0.1313P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2329
_reflns_number_gt                3927
_reflns_number_total             6636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909871b.txt
_cod_data_source_block           3Ni
_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)/c
_cod_database_code               7104658
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 -0.1503(3) 0.6031(5) 0.0548(2) 0.0145(9) Uani 1 1 d . . .
C2 C -0.2052(3) 0.7030(5) 0.0628(2) 0.0154(10) Uani 1 1 d . . .
C3 C -0.3063(3) 0.7443(5) 0.0193(2) 0.0197(10) Uani 1 1 d . . .
H3 H -0.3570 0.7006 -0.0260 0.024 Uiso 1 1 calc R . .
C4 C -0.3302(4) 0.8513(6) 0.0444(3) 0.0228(11) Uani 1 1 d . . .
H4 H -0.3984 0.8836 0.0154 0.027 Uiso 1 1 calc R . .
C5 C -0.2569(4) 0.9121(6) 0.1111(3) 0.0270(12) Uani 1 1 d . . .
H5 H -0.2761 0.9827 0.1274 0.032 Uiso 1 1 calc R . .
C6 C -0.1555(4) 0.8724(6) 0.1548(3) 0.0214(11) Uani 1 1 d . . .
H6 H -0.1051 0.9161 0.2001 0.026 Uiso 1 1 calc R . .
C7 C -0.1311(3) 0.7670(5) 0.1296(2) 0.0146(9) Uani 1 1 d . . .
C8 C -0.0355(3) 0.7113(5) 0.1572(2) 0.0144(10) Uani 1 1 d . . .
C9 C 0.1383(3) 0.7163(5) 0.2417(2) 0.0131(9) Uani 1 1 d . . .
C10 C 0.2302(3) 0.7713(5) 0.3064(2) 0.0144(10) Uani 1 1 d . . .
C11 C 0.2518(3) 0.8688(5) 0.3582(2) 0.0158(10) Uani 1 1 d . . .
H11 H 0.1991 0.9149 0.3519 0.019 Uiso 1 1 calc R . .
C12 C 0.3505(4) 0.8942(5) 0.4172(2) 0.0203(11) Uani 1 1 d . . .
H12 H 0.3670 0.9569 0.4533 0.024 Uiso 1 1 calc R . .
C13 C 0.4281(4) 0.8301(5) 0.4257(2) 0.0201(11) Uani 1 1 d . . .
H13 H 0.4961 0.8519 0.4674 0.024 Uiso 1 1 calc R . .
C14 C 0.4098(3) 0.7363(5) 0.3760(2) 0.0185(10) Uani 1 1 d . . .
H14 H 0.4634 0.6931 0.3826 0.022 Uiso 1 1 calc R . .
C15 C 0.3073(3) 0.7072(5) 0.3146(2) 0.0146(10) Uani 1 1 d . . .
C16 C 0.2595(3) 0.6141(5) 0.2541(2) 0.0152(10) Uani 1 1 d . . .
C17 C 0.2686(3) 0.4449(5) 0.1921(2) 0.0135(9) Uani 1 1 d . . .
C18 C 0.3252(3) 0.3507(5) 0.1845(2) 0.0163(10) Uani 1 1 d . . .
C19 C 0.4287(4) 0.3316(5) 0.2263(2) 0.0204(11) Uani 1 1 d . . .
H19 H 0.4770 0.3896 0.2680 0.024 Uiso 1 1 calc R . .
C20 C 0.4583(4) 0.2256(5) 0.2047(2) 0.0210(11) Uani 1 1 d . . .
H20 H 0.5283 0.2118 0.2319 0.025 Uiso 1 1 calc R . .
C21 C 0.3885(4) 0.1381(6) 0.1442(2) 0.0214(11) Uani 1 1 d . . .
H21 H 0.4113 0.0657 0.1310 0.026 Uiso 1 1 calc R . .
C22 C 0.2858(4) 0.1563(5) 0.1033(2) 0.0200(10) Uani 1 1 d . . .
H22 H 0.2375 0.0974 0.0619 0.024 Uiso 1 1 calc R . .
C23 C 0.2563(3) 0.2618(5) 0.1245(2) 0.0151(10) Uani 1 1 d . . .
C24 C 0.1570(3) 0.3100(5) 0.0963(2) 0.0148(10) Uani 1 1 d . . .
C25 C -0.0265(3) 0.2849(5) 0.0035(2) 0.0144(9) Uani 1 1 d . . .
C26 C -0.0982(4) 0.2030(5) -0.0586(2) 0.0178(10) Uani 1 1 d . . .
H26 H -0.0767 0.1323 -0.0734 0.021 Uiso 1 1 calc R . .
C27 C -0.1996(4) 0.2234(5) -0.0986(2) 0.0190(10) Uani 1 1 d . . .
H27 H -0.2484 0.1667 -0.1407 0.023 Uiso 1 1 calc R . .
C28 C -0.2293(4) 0.3264(5) -0.0770(2) 0.0186(10) Uani 1 1 d . . .
H28 H -0.2990 0.3410 -0.1036 0.022 Uiso 1 1 calc R . .
C29 C -0.1551(3) 0.4119(5) -0.0144(2) 0.0144(9) Uani 1 1 d . . .
C30 C -0.0501(3) 0.3961(5) 0.0296(2) 0.0157(10) Uani 1 1 d . . .
C31 C 0.0959(4) 0.5395(7) 0.4338(3) 0.0331(13) Uani 1 1 d . . .
H31 H 0.1666 0.5577 0.4663 0.040 Uiso 1 1 calc R . .
C32 C -0.0697(5) 0.6084(8) 0.3228(3) 0.0491(17) Uani 1 1 d . . .
H32A H -0.0894 0.5148 0.3313 0.074 Uiso 1 1 calc R . .
H32B H -0.0954 0.6043 0.2758 0.074 Uiso 1 1 calc R . .
H32C H -0.0981 0.6981 0.3264 0.074 Uiso 1 1 calc R . .
C33 C 0.0831(6) 0.7299(7) 0.3612(4) 0.0503(18) Uani 1 1 d . . .
H33A H 0.1568 0.7287 0.4004 0.076 Uiso 1 1 calc R . .
H33B H 0.0575 0.8327 0.3567 0.076 Uiso 1 1 calc R . .
H33C H 0.0652 0.7028 0.3178 0.076 Uiso 1 1 calc R . .
C34 C 0.5034(4) 0.4471(7) 0.8627(3) 0.0342(13) Uani 1 1 d . . .
H34 H 0.4774 0.5286 0.8302 0.041 Uiso 1 1 calc R . .
C35 C 0.3282(4) 0.3783(9) 0.7936(4) 0.066(2) Uani 1 1 d . . .
H35A H 0.3161 0.4743 0.7695 0.098 Uiso 1 1 calc R . .
H35B H 0.2998 0.3862 0.8140 0.098 Uiso 1 1 calc R . .
H35C H 0.2957 0.2932 0.7600 0.098 Uiso 1 1 calc R . .
C36 C 0.4696(5) 0.2213(8) 0.8945(3) 0.060(2) Uani 1 1 d . . .
H36A H 0.5395 0.1957 0.9191 0.089 Uiso 1 1 calc R . .
H36B H 0.4259 0.1328 0.8666 0.089 Uiso 1 1 calc R . .
H36C H 0.4661 0.2473 0.9287 0.089 Uiso 1 1 calc R . .
N1 N -0.1974(3) 0.5140(4) -0.00073(18) 0.0142(8) Uani 1 1 d . . .
H1 H -0.2637 0.5205 -0.0329 0.017 Uiso 1 1 calc R . .
N2 N -0.0502(3) 0.6090(4) 0.10920(18) 0.0123(8) Uani 1 1 d . . .
N3 N 0.0491(3) 0.7577(4) 0.21734(18) 0.0152(8) Uani 1 1 d . . .
N4 N 0.1573(3) 0.6200(4) 0.21069(18) 0.0128(8) Uani 1 1 d . . .
N5 N 0.3124(3) 0.5345(4) 0.24489(19) 0.0146(8) Uani 1 1 d . . .
N6 N 0.1634(3) 0.4144(4) 0.13605(17) 0.0122(8) Uani 1 1 d . . .
N7 N 0.0725(3) 0.2505(4) 0.03804(18) 0.0142(8) Uani 1 1 d . . .
H7 H 0.0798 0.1791 0.0183 0.017 Uiso 1 1 calc R . .
N8 N 0.0391(3) 0.6203(4) 0.3742(2) 0.0194(9) Uani 1 1 d . . .
N9 N 0.4365(3) 0.3502(5) 0.8490(2) 0.0297(11) Uani 1 1 d . . .
Ni1 Ni 0.05359(5) 0.50918(7) 0.11961(3) 0.0235(2) Uani 1 1 d . . .
O1 O 0.0686(3) 0.4478(4) 0.45074(16) 0.0229(8) Uani 1 1 d . . .
O2 O 0.5939(3) 0.4445(5) 0.9116(2) 0.0394(10) 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'
Ni Ni 0.3393 1.1124 '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 N2 124.9(4) . . ?
N1 C1 C2 121.9(4) . . ?
N2 C1 C2 113.2(4) . . ?
C3 C2 C7 121.0(4) . . ?
C3 C2 C1 134.1(4) . . ?
C7 C2 C1 104.9(4) . . ?
C4 C3 C2 117.5(4) . . ?
C3 C4 C5 121.3(5) . . ?
C4 C5 C6 121.5(4) . . ?
C7 C6 C5 117.4(4) . . ?
C6 C7 C2 121.3(4) . . ?
C6 C7 C8 132.0(4) . . ?
C2 C7 C8 106.5(4) . . ?
N3 C8 N2 128.2(4) . . ?
N3 C8 C7 121.3(4) . . ?
N2 C8 C7 110.4(4) . . ?
N3 C9 N4 127.8(4) . . ?
N3 C9 C10 122.0(4) . . ?
N4 C9 C10 110.2(4) . . ?
C15 C10 C11 121.2(4) . . ?
C15 C10 C9 106.4(4) . . ?
C11 C10 C9 132.4(4) . . ?
C12 C11 C10 117.7(4) . . ?
C11 C12 C13 121.3(4) . . ?
C14 C13 C12 122.5(4) . . ?
C13 C14 C15 116.8(4) . . ?
C10 C15 C14 120.4(4) . . ?
C10 C15 C16 106.6(4) . . ?
C14 C15 C16 133.0(4) . . ?
N5 C16 N4 127.7(4) . . ?
N5 C16 C15 122.4(4) . . ?
N4 C16 C15 109.9(4) . . ?
N5 C17 N6 128.4(4) . . ?
N5 C17 C18 121.9(4) . . ?
N6 C17 C18 109.7(4) . . ?
C23 C18 C19 119.9(4) . . ?
C23 C18 C17 107.6(4) . . ?
C19 C18 C17 132.4(4) . . ?
C20 C19 C18 117.6(4) . . ?
C19 C20 C21 121.9(4) . . ?
C22 C21 C20 120.3(4) . . ?
C23 C22 C21 117.8(4) . . ?
C22 C23 C18 122.5(4) . . ?
C22 C23 C24 133.3(4) . . ?
C18 C23 C24 104.2(4) . . ?
N7 C24 N6 125.4(4) . . ?
N7 C24 C23 121.4(4) . . ?
N6 C24 C23 113.2(4) . . ?
N7 C25 C26 113.6(4) . . ?
N7 C25 C30 122.0(4) . . ?
C26 C25 C30 124.4(4) . . ?
C27 C26 C25 120.7(4) . . ?
C28 C27 C26 118.9(4) . . ?
C27 C28 C29 119.6(4) . . ?
N1 C29 C30 122.8(4) . . ?
N1 C29 C28 112.5(4) . . ?
C30 C29 C28 124.7(4) . . ?
C29 C30 C25 111.7(4) . . ?
C29 C30 Ni1 124.5(3) . . ?
C25 C30 Ni1 123.8(3) . . ?
O1 C31 N8 127.7(5) . . ?
O2 C34 N9 127.7(6) . . ?
C1 N1 C29 128.0(4) . . ?
C1 N2 C8 104.8(4) . . ?
C1 N2 Ni1 128.3(3) . . ?
C8 N2 Ni1 126.8(3) . . ?
C8 N3 C9 122.4(4) . . ?
C16 N4 C9 106.9(3) . . ?
C16 N4 Ni1 127.0(3) . . ?
C9 N4 Ni1 126.1(3) . . ?
C17 N5 C16 121.6(4) . . ?
C24 N6 C17 105.3(4) . . ?
C24 N6 Ni1 127.4(3) . . ?
C17 N6 Ni1 127.3(3) . . ?
C24 N7 C25 128.9(4) . . ?
C31 N8 C33 121.5(5) . . ?
C31 N8 C32 120.9(5) . . ?
C33 N8 C32 117.5(5) . . ?
C34 N9 C36 119.8(5) . . ?
C34 N9 C35 122.1(6) . . ?
C36 N9 C35 117.7(5) . . ?
N6 Ni1 N2 176.34(14) . . ?
N6 Ni1 C30 92.36(17) . . ?
N2 Ni1 C30 91.23(17) . . ?
N6 Ni1 N4 87.80(15) . . ?
N2 Ni1 N4 88.60(15) . . ?
C30 Ni1 N4 179.02(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 N1 1.322(6) . ?
C1 N2 1.336(6) . ?
C1 C2 1.455(6) . ?
C2 C3 1.393(6) . ?
C2 C7 1.397(6) . ?
C3 C4 1.382(6) . ?
C4 C5 1.383(7) . ?
C5 C6 1.393(7) . ?
C6 C7 1.380(6) . ?
C7 C8 1.440(6) . ?
C8 N3 1.296(5) . ?
C8 N2 1.417(5) . ?
C9 N3 1.328(6) . ?
C9 N4 1.378(5) . ?
C9 C10 1.416(6) . ?
C10 C15 1.392(6) . ?
C10 C11 1.416(6) . ?
C11 C12 1.360(6) . ?
C12 C13 1.396(7) . ?
C13 C14 1.378(6) . ?
C14 C15 1.416(6) . ?
C15 C16 1.430(6) . ?
C16 N5 1.347(6) . ?
C16 N4 1.362(6) . ?
C17 N5 1.285(6) . ?
C17 N6 1.424(5) . ?
C17 C18 1.444(6) . ?
C18 C23 1.392(6) . ?
C18 C19 1.396(6) . ?
C19 C20 1.380(7) . ?
C20 C21 1.394(7) . ?
C21 C22 1.386(7) . ?
C22 C23 1.369(6) . ?
C23 C24 1.474(6) . ?
C24 N7 1.318(6) . ?
C24 N6 1.333(6) . ?
C25 N7 1.388(6) . ?
C25 C26 1.395(6) . ?
C25 C30 1.421(6) . ?
C26 C27 1.374(7) . ?
C27 C28 1.365(6) . ?
C28 C29 1.424(6) . ?
C29 N1 1.384(6) . ?
C29 C30 1.407(6) . ?
C30 Ni1 1.995(5) . ?
C31 O1 1.186(6) . ?
C31 N8 1.337(7) . ?
C32 N8 1.444(7) . ?
C33 N8 1.439(7) . ?
C34 O2 1.206(6) . ?
C34 N9 1.318(7) . ?
C35 N9 1.457(7) . ?
C36 N9 1.437(8) . ?
N2 Ni1 1.934(4) . ?
N4 Ni1 2.002(4) . ?
N6 Ni1 1.930(4) . ?
