#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:42:58 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/73/4037394.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_4037394
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 H63 N5 O4'
_chemical_formula_weight         822.07
_chemical_melting_point          537
_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                 92.499(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3848(16)
_cell_length_b                   20.457(5)
_cell_length_c                   16.933(4)
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    93
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.41
_cell_volume                     2209.6(9)
_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 0.959
_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  0.0738
_diffrn_reflns_av_sigmaI/netI    0.1101
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12324
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0912
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2728
_refine_ls_wR_factor_ref         0.3211
_reflns_number_gt                2703
_reflns_number_total             4853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02159_si_002.cif
_cod_data_source_block           3a(2H)
_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_cell_volume        2209.6(10)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4037394
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
N1 N 0.6855(5) 0.46359(16) 0.5888(2) 0.0236(8) Uani 1 1 d . . .
N2 N 0.2958(5) 0.42157(16) 0.51790(19) 0.0227(8) Uani 1 1 d . . .
H2B H 0.3847 0.4539 0.5117 0.027 Uiso 1 1 calc R . .
C1 C 0.8718(7) 0.4900(2) 0.6158(2) 0.0253(10) Uani 1 1 d . . .
C2 C 0.9598(7) 0.4535(2) 0.6823(2) 0.0261(10) Uani 1 1 d . . .
H2A H 1.0871 0.4625 0.7115 0.031 Uiso 1 1 calc R . .
C3 C 0.8260(7) 0.4041(2) 0.6948(2) 0.0264(10) Uani 1 1 d . . .
H3A H 0.8399 0.3719 0.7351 0.032 Uiso 1 1 calc R . .
C4 C 0.6565(7) 0.4094(2) 0.6354(2) 0.0248(9) Uani 1 1 d . . .
C5 C 0.4886(7) 0.3652(2) 0.6275(2) 0.0242(9) Uani 1 1 d . . .
C6 C 0.3219(7) 0.3717(2) 0.5721(2) 0.0230(9) Uani 1 1 d . . .
C7 C 0.1421(7) 0.3302(2) 0.5616(2) 0.0252(9) Uani 1 1 d . . .
H7A H 0.1158 0.2917 0.5910 0.030 Uiso 1 1 calc R . .
C8 C 0.0152(7) 0.3553(2) 0.5022(2) 0.0258(10) Uani 1 1 d . . .
H8A H -0.1139 0.3372 0.4826 0.031 Uiso 1 1 calc R . .
C9 C 0.1102(7) 0.4133(2) 0.4749(2) 0.0237(9) Uani 1 1 d . B .
C10 C 0.0293(7) 0.4548(2) 0.4151(2) 0.0247(9) Uani 1 1 d . . .
H10A H -0.1063 0.4445 0.3933 0.030 Uiso 0.50 1 calc PR A 2
N3 N -0.1694(12) 0.4407(3) 0.3889(4) 0.0295(17) Uani 0.50 1 d P B 1
H3B H -0.2368 0.4077 0.4094 0.035 Uiso 0.50 1 calc PR B 1
H3C H -0.2309 0.4646 0.3514 0.035 Uiso 0.50 1 calc PR B 1
C11 C 0.4943(7) 0.3053(2) 0.6780(2) 0.0242(9) Uani 1 1 d . . .
C12 C 0.6519(7) 0.2597(2) 0.6698(2) 0.0264(10) Uani 1 1 d . . .
H12A H 0.7543 0.2664 0.6316 0.032 Uiso 1 1 calc R . .
C13 C 0.6613(7) 0.2036(2) 0.7174(3) 0.0268(10) Uani 1 1 d . . .
C14 C 0.5128(7) 0.1942(2) 0.7739(2) 0.0267(10) Uani 1 1 d . . .
H14A H 0.5180 0.1564 0.8065 0.032 Uiso 1 1 calc R . .
C15 C 0.3566(7) 0.2406(2) 0.7821(2) 0.0250(10) Uani 1 1 d . . .
C16 C 0.3435(7) 0.2962(2) 0.7347(2) 0.0264(10) Uani 1 1 d . . .
H16A H 0.2347 0.3273 0.7407 0.032 Uiso 1 1 calc R . .
C17 C 0.8396(8) 0.1050(2) 0.7545(3) 0.0337(11) Uani 1 1 d . . .
H17A H 0.7073 0.0797 0.7509 0.040 Uiso 1 1 calc R . .
H17B H 0.8658 0.1186 0.8102 0.040 Uiso 1 1 calc R . .
C18 C 1.0164(8) 0.0638(2) 0.7285(3) 0.0333(11) Uani 1 1 d . . .
H18A H 1.0282 0.0251 0.7635 0.040 Uiso 1 1 calc R . .
H18B H 1.1478 0.0891 0.7362 0.040 Uiso 1 1 calc R . .
C19 C 0.9999(8) 0.0398(2) 0.6424(3) 0.0340(11) Uani 1 1 d . . .
H19A H 1.0182 0.0784 0.6070 0.041 Uiso 1 1 calc R . .
C20 C 1.1762(9) -0.0082(3) 0.6284(3) 0.0452(14) Uani 1 1 d . . .
H20A H 1.1725 -0.0208 0.5725 0.068 Uiso 1 1 calc R . .
H20B H 1.1584 -0.0472 0.6611 0.068 Uiso 1 1 calc R . .
H20C H 1.3112 0.0123 0.6426 0.068 Uiso 1 1 calc R . .
C21 C 0.7898(8) 0.0095(3) 0.6216(3) 0.0422(13) Uani 1 1 d . . .
H21A H 0.7870 -0.0059 0.5668 0.063 Uiso 1 1 calc R . .
H21B H 0.6794 0.0422 0.6275 0.063 Uiso 1 1 calc R . .
H21C H 0.7663 -0.0274 0.6570 0.063 Uiso 1 1 calc R . .
C22 C 0.0814(8) 0.2774(2) 0.8641(3) 0.0296(10) Uani 1 1 d . . .
H22A H -0.0339 0.2822 0.8235 0.036 Uiso 1 1 calc R . .
H22B H 0.1558 0.3197 0.8696 0.036 Uiso 1 1 calc R . .
C23 C -0.0048(8) 0.2573(2) 0.9421(3) 0.0311(11) Uani 1 1 d . . .
H23A H 0.1142 0.2453 0.9787 0.037 Uiso 1 1 calc R . .
H23B H -0.0919 0.2177 0.9334 0.037 Uiso 1 1 calc R . .
C24 C -0.1366(7) 0.3090(2) 0.9823(3) 0.0302(10) Uani 1 1 d . . .
H24A H -0.1754 0.2903 1.0343 0.036 Uiso 1 1 calc R . .
C25 C -0.0139(9) 0.3714(2) 1.0005(3) 0.0411(12) Uani 1 1 d . . .
H25A H 0.1231 0.3602 1.0252 0.062 Uiso 1 1 calc R . .
H25B H -0.0917 0.3987 1.0366 0.062 Uiso 1 1 calc R . .
H25C H 0.0059 0.3954 0.9513 0.062 Uiso 1 1 calc R . .
C26 C -0.3419(8) 0.3232(2) 0.9355(3) 0.0355(11) Uani 1 1 d . . .
H26A H -0.4283 0.3528 0.9659 0.053 Uiso 1 1 calc R . .
H26B H -0.4179 0.2822 0.9255 0.053 Uiso 1 1 calc R . .
H26C H -0.3111 0.3437 0.8850 0.053 Uiso 1 1 calc R . .
O1 O 0.8220(5) 0.16198(15) 0.70398(18) 0.0325(8) Uani 1 1 d . . .
O2 O 0.2227(5) 0.22728(15) 0.84168(17) 0.0300(8) 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'
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
C1 N1 C4 105.3(3) . .
C9 N2 C6 109.8(3) . .
C9 N2 H2B 125.1 . .
C6 N2 H2B 125.1 . .
N1 C1 C10 126.2(4) . 3_666
N1 C1 C2 111.1(4) . .
C10 C1 C2 122.7(4) 3_666 .
C3 C2 C1 106.4(4) . .
C3 C2 H2A 126.8 . .
C1 C2 H2A 126.8 . .
C2 C3 C4 107.2(4) . .
C2 C3 H3A 126.4 . .
C4 C3 H3A 126.4 . .
N1 C4 C5 125.8(4) . .
N1 C4 C3 110.0(4) . .
C5 C4 C3 124.2(4) . .
C6 C5 C4 124.1(4) . .
C6 C5 C11 117.5(4) . .
C4 C5 C11 118.3(4) . .
N2 C6 C5 125.8(4) . .
N2 C6 C7 106.4(4) . .
C5 C6 C7 127.7(4) . .
C8 C7 C6 108.4(4) . .
C8 C7 H7A 125.8 . .
C6 C7 H7A 125.8 . .
C7 C8 C9 107.8(4) . .
C7 C8 H8A 126.1 . .
C9 C8 H8A 126.1 . .
N2 C9 C10 126.2(4) . .
N2 C9 C8 107.6(4) . .
C10 C9 C8 126.3(4) . .
N3 C10 C9 114.7(5) . .
N3 C10 C1 118.5(5) . 3_666
C9 C10 C1 126.7(4) . 3_666
N3 C10 H10A 3.9 . .
C9 C10 H10A 116.6 . .
C1 C10 H10A 116.6 3_666 .
C10 N3 H3B 120.0 . .
C10 N3 H3C 120.0 . .
H3B N3 H3C 120.0 . .
C12 C11 C16 120.2(4) . .
C12 C11 C5 119.7(4) . .
C16 C11 C5 120.1(4) . .
C11 C12 C13 120.5(4) . .
C11 C12 H12A 119.8 . .
C13 C12 H12A 119.8 . .
O1 C13 C14 124.9(4) . .
O1 C13 C12 115.4(4) . .
C14 C13 C12 119.7(4) . .
C15 C14 C13 119.3(4) . .
C15 C14 H14A 120.4 . .
C13 C14 H14A 120.4 . .
O2 C15 C14 114.2(4) . .
O2 C15 C16 124.1(4) . .
C14 C15 C16 121.8(4) . .
C15 C16 C11 118.5(4) . .
C15 C16 H16A 120.7 . .
C11 C16 H16A 120.7 . .
O1 C17 C18 108.7(4) . .
O1 C17 H17A 109.9 . .
C18 C17 H17A 109.9 . .
O1 C17 H17B 109.9 . .
C18 C17 H17B 109.9 . .
H17A C17 H17B 108.3 . .
C17 C18 C19 116.0(4) . .
C17 C18 H18A 108.3 . .
C19 C18 H18A 108.3 . .
C17 C18 H18B 108.3 . .
C19 C18 H18B 108.3 . .
H18A C18 H18B 107.4 . .
C21 C19 C20 110.8(4) . .
C21 C19 C18 112.1(4) . .
C20 C19 C18 109.5(4) . .
C21 C19 H19A 108.1 . .
C20 C19 H19A 108.1 . .
C18 C19 H19A 108.1 . .
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 107.2(3) . .
O2 C22 H22A 110.3 . .
C23 C22 H22A 110.3 . .
O2 C22 H22B 110.3 . .
C23 C22 H22B 110.3 . .
H22A C22 H22B 108.5 . .
C22 C23 C24 115.5(4) . .
C22 C23 H23A 108.4 . .
C24 C23 H23A 108.4 . .
C22 C23 H23B 108.4 . .
C24 C23 H23B 108.4 . .
H23A C23 H23B 107.5 . .
C25 C24 C26 111.6(4) . .
C25 C24 C23 112.4(4) . .
C26 C24 C23 112.1(4) . .
C25 C24 H24A 106.8 . .
C26 C24 H24A 106.8 . .
C23 C24 H24A 106.8 . .
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 . .
C13 O1 C17 116.4(3) . .
C15 O2 C22 118.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.367(5) .
N1 C4 1.378(5) .
N2 C9 1.374(5) .
N2 C6 1.378(5) .
N2 H2B 0.8800 .
C1 C10 1.406(6) 3_666
C1 C2 1.445(6) .
C2 C3 1.346(6) .
C2 H2A 0.9500 .
C3 C4 1.450(6) .
C3 H3A 0.9500 .
C4 C5 1.403(6) .
C5 C6 1.394(6) .
C5 C11 1.494(6) .
C6 C7 1.432(6) .
C7 C8 1.365(6) .
C7 H7A 0.9500 .
C8 C9 1.419(6) .
C8 H8A 0.9500 .
C9 C10 1.402(6) .
C10 N3 1.357(8) .
C10 C1 1.406(6) 3_666
C10 H10A 0.9500 .
N3 H3B 0.8800 .
N3 H3C 0.8800 .
C11 C12 1.384(6) .
C11 C16 1.401(6) .
C12 C13 1.403(6) .
C12 H12A 0.9500 .
C13 O1 1.360(5) .
C13 C14 1.389(6) .
C14 C15 1.389(6) .
C14 H14A 0.9500 .
C15 O2 1.378(5) .
C15 C16 1.392(6) .
C16 H16A 0.9500 .
C17 O1 1.448(5) .
C17 C18 1.491(6) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.538(7) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C21 1.505(7) .
C19 C20 1.521(7) .
C19 H19A 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 O2 1.428(5) .
C22 C23 1.510(6) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.530(6) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.521(7) .
C24 C26 1.530(7) .
C24 H24A 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 .
