#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:42:58 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/73/4037396.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_4037396
loop_
_publ_author_name
'Yamashita, Ken-Ichi'
'Kataoka, Kazuyuki'
'Takeuchi, Shouichi'
'Sugiura, Ken-Ichi'
_publ_contact_author             'Ken-ichi Yamashita'
_publ_section_title
;
 Metal-Free Synthesis of meso-Aminoporphyrins through Reduction of
 meso-Azidoporphyrins Generated in Situ by Nucleophilic Substitution
 Reactions of meso-Bromoporphyrins.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11176
_journal_page_last               11184
_journal_paper_doi               10.1021/acs.joc.6b02159
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C52 H61 Cu N5 O4'
_chemical_formula_weight         883.60
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 92.3450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3352(4)
_cell_length_b                   20.2924(12)
_cell_length_c                   17.0320(10)
_cell_measurement_reflns_used    3759
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.34
_cell_volume                     2187.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'omega scan'
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12675
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.9168
_exptl_absorpt_correction_T_min  0.8788
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             938
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0519
_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)+(0.0593P)²+1.8367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                4207
_reflns_number_total             4935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02159_si_002.cif
_cod_data_source_block           3a(Cu)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4037396
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
Cu1 Cu 0.0000 0.0000 1.0000 0.01418(13) Uani 1 2 d S . .
N1 N -0.1904(3) 0.03282(9) 0.91160(11) 0.0144(4) Uani 1 1 d . . .
N2 N 0.1950(3) 0.07586(9) 0.98337(11) 0.0137(4) Uani 1 1 d . . .
O1 O -0.3380(3) 0.33634(9) 0.79603(11) 0.0224(4) Uani 1 1 d . . .
O2 O 0.2660(3) 0.27210(8) 0.65765(10) 0.0202(4) Uani 1 1 d . . .
C1 C -0.3779(4) 0.00558(11) 0.88468(13) 0.0149(5) Uani 1 1 d . . .
C2 C -0.4652(4) 0.04227(12) 0.81932(14) 0.0184(5) Uani 1 1 d . . .
H2 H -0.5929 0.0329 0.7903 0.022 Uiso 1 1 calc R . .
C3 C -0.3316(4) 0.09266(12) 0.80683(14) 0.0180(5) Uani 1 1 d . . .
H3 H -0.3470 0.1253 0.7670 0.022 Uiso 1 1 calc R . .
C4 C -0.1619(4) 0.08777(12) 0.86496(13) 0.0151(5) Uani 1 1 d . . .
C5 C 0.0049(4) 0.13261(11) 0.87316(13) 0.0154(5) Uani 1 1 d . . .
C6 C 0.1723(4) 0.12578(11) 0.92825(13) 0.0149(5) Uani 1 1 d . . .
C7 C 0.3499(4) 0.16994(12) 0.93525(14) 0.0172(5) Uani 1 1 d . . .
H7 H 0.3710 0.2084 0.9048 0.021 Uiso 1 1 calc R . .
C8 C 0.4810(4) 0.14643(12) 0.99327(14) 0.0174(5) Uani 1 1 d . . .
H8 H 0.6120 0.1650 1.0110 0.021 Uiso 1 1 calc R . .
C9 C 0.3849(4) 0.08820(11) 1.02299(13) 0.0164(5) Uani 1 1 d . B .
C10 C 0.4728(4) 0.05025(12) 1.08367(14) 0.0172(5) Uani 1 1 d . . .
H10A H 0.6071 0.0631 1.1053 0.021 Uiso 0.50 1 calc PR A 2
N3 N 0.6850(7) 0.0665(2) 1.1073(2) 0.0188(9) Uani 0.50 1 d P B 1
H3A H 0.7506 0.0987 1.0837 0.023 Uiso 0.50 1 calc PR B 1
H3B H 0.7504 0.0444 1.1455 0.023 Uiso 0.50 1 calc PR B 1
C11 C -0.0023(4) 0.19267(12) 0.82157(13) 0.0160(5) Uani 1 1 d . . .
C12 C -0.1611(4) 0.23855(12) 0.83083(13) 0.0172(5) Uani 1 1 d . . .
H12 H -0.2615 0.2321 0.8700 0.021 Uiso 1 1 calc R . .
C13 C -0.1746(4) 0.29444(12) 0.78268(14) 0.0185(5) Uani 1 1 d . . .
C14 C -0.0279(4) 0.30382(12) 0.72542(14) 0.0186(5) Uani 1 1 d . . .
H14 H -0.0369 0.3414 0.6922 0.022 Uiso 1 1 calc R . .
C15 C 0.1325(4) 0.25786(12) 0.71686(13) 0.0171(5) Uani 1 1 d . . .
C16 C 0.1477(4) 0.20218(12) 0.76415(13) 0.0173(5) Uani 1 1 d . . .
H16 H 0.2576 0.1710 0.7578 0.021 Uiso 1 1 calc R . .
C17 C -0.3564(4) 0.39318(13) 0.74546(16) 0.0255(6) Uani 1 1 d . . .
H17A H -0.3902 0.3792 0.6907 0.031 Uiso 1 1 calc R . .
H17B H -0.2213 0.4177 0.7465 0.031 Uiso 1 1 calc R . .
C18 C -0.5308(4) 0.43675(14) 0.77446(16) 0.0263(6) Uani 1 1 d . . .
H18A H -0.6656 0.4121 0.7694 0.032 Uiso 1 1 calc R . .
H18B H -0.5439 0.4757 0.7396 0.032 Uiso 1 1 calc R . .
C19 C -0.5013(4) 0.46091(13) 0.85944(16) 0.0248(6) Uani 1 1 d . . .
H19 H -0.5192 0.4224 0.8953 0.030 Uiso 1 1 calc R . .
C20 C -0.2836(5) 0.49003(14) 0.87628(18) 0.0321(7) Uani 1 1 d . . .
H20A H -0.2609 0.5267 0.8402 0.048 Uiso 1 1 calc R . .
H20B H -0.1761 0.4561 0.8689 0.048 Uiso 1 1 calc R . .
H20C H -0.2732 0.5061 0.9306 0.048 Uiso 1 1 calc R . .
C21 C -0.6709(5) 0.51165(15) 0.87629(19) 0.0355(7) Uani 1 1 d . . .
H21A H -0.6601 0.5240 0.9319 0.053 Uiso 1 1 calc R . .
H21B H -0.8107 0.4927 0.8640 0.053 Uiso 1 1 calc R . .
H21C H -0.6509 0.5508 0.8438 0.053 Uiso 1 1 calc R . .
C22 C 0.4113(4) 0.22144(12) 0.63509(14) 0.0197(5) Uani 1 1 d . . .
H22A H 0.3378 0.1785 0.6296 0.024 Uiso 1 1 calc R . .
H22B H 0.5281 0.2169 0.6751 0.024 Uiso 1 1 calc R . .
C23 C 0.4960(4) 0.24280(13) 0.55694(14) 0.0216(5) Uani 1 1 d . . .
H23A H 0.5812 0.2832 0.5654 0.026 Uiso 1 1 calc R . .
H23B H 0.3750 0.2542 0.5208 0.026 Uiso 1 1 calc R . .
C24 C 0.6319(4) 0.19115(12) 0.51703(15) 0.0211(5) Uani 1 1 d . . .
H24 H 0.6714 0.2103 0.4656 0.025 Uiso 1 1 calc R . .
C25 C 0.5086(5) 0.12842(14) 0.49834(17) 0.0302(6) Uani 1 1 d . . .
H25A H 0.5917 0.0998 0.4650 0.045 Uiso 1 1 calc R . .
H25B H 0.3747 0.1396 0.4707 0.045 Uiso 1 1 calc R . .
H25C H 0.4798 0.1054 0.5473 0.045 Uiso 1 1 calc R . .
C26 C 0.8380(4) 0.17684(14) 0.56331(16) 0.0265(6) Uani 1 1 d . . .
H26A H 0.8068 0.1557 0.6132 0.040 Uiso 1 1 calc R . .
H26B H 0.9139 0.2182 0.5737 0.040 Uiso 1 1 calc R . .
H26C H 0.9257 0.1474 0.5327 0.040 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'
Cu Cu 0.3201 1.2651 '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
N2 Cu1 N2 180.00(7) 3_557 .
N2 Cu1 N1 89.66(8) 3_557 3_557
N2 Cu1 N1 90.34(8) . 3_557
N2 Cu1 N1 90.34(8) 3_557 .
N2 Cu1 N1 89.66(8) . .
N1 Cu1 N1 180.000(1) 3_557 .
C1 N1 C4 105.32(19) . .
C1 N1 Cu1 127.11(16) . .
C4 N1 Cu1 127.57(16) . .
C9 N2 C6 105.28(19) . .
C9 N2 Cu1 127.03(16) . .
C6 N2 Cu1 127.66(16) . .
C13 O1 C17 116.24(19) . .
C15 O2 C22 117.67(18) . .
N1 C1 C10 125.2(2) . 3_557
N1 C1 C2 110.6(2) . .
C10 C1 C2 124.2(2) 3_557 .
C3 C2 C1 107.0(2) . .
C3 C2 H2 126.5 . .
C1 C2 H2 126.5 . .
C2 C3 C4 107.2(2) . .
C2 C3 H3 126.4 . .
C4 C3 H3 126.4 . .
N1 C4 C5 125.6(2) . .
N1 C4 C3 109.9(2) . .
C5 C4 C3 124.5(2) . .
C6 C5 C4 123.6(2) . .
C6 C5 C11 118.6(2) . .
C4 C5 C11 117.7(2) . .
N2 C6 C5 125.8(2) . .
N2 C6 C7 109.9(2) . .
C5 C6 C7 124.4(2) . .
C8 C7 C6 107.2(2) . .
C8 C7 H7 126.4 . .
C6 C7 H7 126.4 . .
C7 C8 C9 107.0(2) . .
C7 C8 H8 126.5 . .
C9 C8 H8 126.5 . .
N2 C9 C10 125.4(2) . .
N2 C9 C8 110.6(2) . .
C10 C9 C8 124.0(2) . .
C9 C10 C1 124.8(2) . 3_557
C9 C10 N3 115.3(3) . .
C1 C10 N3 119.5(3) 3_557 .
C9 C10 H10A 117.6 . .
C1 C10 H10A 117.6 3_557 .
N3 C10 H10A 7.2 . .
C10 N3 H3A 120.0 . .
C10 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C12 C11 C16 120.2(2) . .
C12 C11 C5 118.9(2) . .
C16 C11 C5 120.9(2) . .
C11 C12 C13 120.3(2) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
O1 C13 C14 124.4(2) . .
O1 C13 C12 115.8(2) . .
C14 C13 C12 119.7(2) . .
C13 C14 C15 119.7(2) . .
C13 C14 H14 120.2 . .
C15 C14 H14 120.2 . .
O2 C15 C16 124.6(2) . .
O2 C15 C14 114.2(2) . .
C16 C15 C14 121.2(2) . .
C15 C16 C11 118.9(2) . .
C15 C16 H16 120.6 . .
C11 C16 H16 120.6 . .
O1 C17 C18 108.4(2) . .
O1 C17 H17A 110.0 . .
C18 C17 H17A 110.0 . .
O1 C17 H17B 110.0 . .
C18 C17 H17B 110.0 . .
H17A C17 H17B 108.4 . .
C17 C18 C19 115.6(2) . .
C17 C18 H18A 108.4 . .
C19 C18 H18A 108.4 . .
C17 C18 H18B 108.4 . .
C19 C18 H18B 108.4 . .
H18A C18 H18B 107.4 . .
C20 C19 C21 110.1(2) . .
C20 C19 C18 112.2(2) . .
C21 C19 C18 109.5(2) . .
C20 C19 H19 108.3 . .
C21 C19 H19 108.3 . .
C18 C19 H19 108.3 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O2 C22 C23 106.39(19) . .
O2 C22 H22A 110.5 . .
C23 C22 H22A 110.5 . .
O2 C22 H22B 110.5 . .
C23 C22 H22B 110.5 . .
H22A C22 H22B 108.6 . .
C22 C23 C24 114.7(2) . .
C22 C23 H23A 108.6 . .
C24 C23 H23A 108.6 . .
C22 C23 H23B 108.6 . .
C24 C23 H23B 108.6 . .
H23A C23 H23B 107.6 . .
C25 C24 C26 111.7(2) . .
C25 C24 C23 111.8(2) . .
C26 C24 C23 112.7(2) . .
C25 C24 H24 106.7 . .
C26 C24 H24 106.7 . .
C23 C24 H24 106.7 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 2.0012(19) 3_557
Cu1 N2 2.0012(19) .
Cu1 N1 2.0043(19) 3_557
Cu1 N1 2.0043(19) .
N1 C1 1.372(3) .
N1 C4 1.385(3) .
N2 C9 1.378(3) .
N2 C6 1.385(3) .
O1 C13 1.366(3) .
O1 C17 1.441(3) .
O2 C15 1.373(3) .
O2 C22 1.442(3) .
C1 C10 1.401(3) 3_557
C1 C2 1.431(3) .
C2 C3 1.350(3) .
C2 H2 0.9500 .
C3 C4 1.435(3) .
C3 H3 0.9500 .
C4 C5 1.397(3) .
C5 C6 1.394(3) .
C5 C11 1.502(3) .
C6 C7 1.440(3) .
C7 C8 1.352(3) .
C7 H7 0.9500 .
C8 C9 1.431(3) .
C8 H8 0.9500 .
C9 C10 1.387(3) .
C10 C1 1.401(3) 3_557
C10 N3 1.427(5) .
C10 H10A 0.9500 .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
C11 C12 1.385(3) .
C11 C16 1.405(3) .
C12 C13 1.400(3) .
C12 H12 0.9500 .
C13 C14 1.388(3) .
C14 C15 1.391(3) .
C14 H14 0.9500 .
C15 C16 1.389(3) .
C16 H16 0.9500 .
C17 C18 1.513(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.532(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.517(4) .
C19 C21 1.524(4) .
C19 H19 1.0000 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C23 1.519(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.533(3) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.521(4) .
C24 C26 1.525(4) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
