#------------------------------------------------------------------------------
#$Date: 2020-02-04 22:05:45 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125649.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_7125649
loop_
_publ_author_name
'Bousfiha, Asmae'
'Dimé, Abdou K D'
'Mankou-Makaya, Amelle'
'Echaubard, Julie'
'Berthelot, Mathieu'
'Cattey, Hélène'
'Romieu, Anthony'
'Roger, Julien'
'Devillers, Charles H.'
_publ_section_title
;
 Regioselective C-H amination of free base porphyrins via electrogenerated
 pyridinium-porphyrins and stabilization of easily oxidized
 amino-porphyrins by protonation.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              884
_journal_page_last               887
_journal_paper_doi               10.1039/c9cc07351e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C44 H31 N5'
_chemical_formula_sum            'C44 H31 N5'
_chemical_formula_weight         629.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.209(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.7683(9)
_cell_length_b                   9.6009(5)
_cell_length_c                   12.4544(7)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.02
_cell_volume                     1610.60(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       'φ and ω scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39621
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0756 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.8387.'
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       prism
_exptl_crystal_F_000             660
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and ether  by slow evaporation'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0560P)²+1.4297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2840
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc07351e2.cif
_cod_data_source_block           H2TPP-NH2
_cod_depositor_comments
'Adding full bibliography for 7125649--7125650.cif.'
_cod_database_code               7125649
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: H2(0.5) N3(0.5) H3A(0.5) H3B(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48101(13) 0.38515(18) 0.72342(15) 0.0212(4) Uani 1 1 d . . . .
N1 N 0.54426(10) 0.41466(15) 0.67031(13) 0.0221(3) Uani 1 1 d . . . .
H1 H 0.526996 0.457788 0.602429 0.027 Uiso 1 1 calc R . . .
C2 C 0.53928(13) 0.31313(18) 0.83134(15) 0.0227(4) Uani 1 1 d . . . .
H2 H 0.515941 0.278772 0.886913 0.027 Uiso 0.5 1 calc R P A 2
N2 N 0.64069(11) 0.48526(15) 0.51499(12) 0.0212(3) Uani 1 1 d . . . .
C3 C 0.63410(13) 0.30314(18) 0.83936(15) 0.0230(4) Uani 1 1 d . . . .
H3 H 0.688286 0.260566 0.901870 0.028 Uiso 1 1 calc R . . .
N3 N 0.5092(2) 0.2625(4) 0.9140(3) 0.0306(7) Uani 0.5 1 d . P B 1
H3A H 0.551975 0.220341 0.977134 0.037 Uiso 0.5 1 calc R P B 1
H3B H 0.446939 0.272005 0.903995 0.037 Uiso 0.5 1 calc R P B 1
C4 C 0.63810(13) 0.36717(18) 0.73845(15) 0.0224(4) Uani 1 1 d . . . .
C5 C 0.72122(13) 0.37530(18) 0.71121(15) 0.0220(4) Uani 1 1 d . . . .
C6 C 0.72107(13) 0.43014(18) 0.60692(15) 0.0214(4) Uani 1 1 d . . . .
C7 C 0.80896(13) 0.43461(18) 0.58175(15) 0.0230(4) Uani 1 1 d . . . .
H7 H 0.873672 0.403142 0.631434 0.028 Uiso 1 1 calc R . . .
C8 C 0.78064(13) 0.49189(18) 0.47460(15) 0.0221(4) Uani 1 1 d . . . .
H8 H 0.821479 0.508200 0.433560 0.026 Uiso 1 1 calc R . . .
C9 C 0.67573(13) 0.52420(17) 0.43331(15) 0.0207(4) Uani 1 1 d . . . .
C10 C 0.62011(13) 0.58420(17) 0.32249(15) 0.0208(4) Uani 1 1 d . . . .
C11 C 0.81687(13) 0.32147(19) 0.80249(16) 0.0243(4) Uani 1 1 d . . . .
C12 C 0.86415(14) 0.2068(2) 0.77941(18) 0.0304(4) Uani 1 1 d . . . .
H12 H 0.835571 0.162212 0.704832 0.036 Uiso 1 1 calc R . . .
C13 C 0.95324(15) 0.1573(2) 0.8654(2) 0.0384(5) Uani 1 1 d . . . .
H13 H 0.985484 0.079888 0.848726 0.046 Uiso 1 1 calc R . . .
C14 C 0.99458(15) 0.2202(2) 0.97429(19) 0.0383(5) Uani 1 1 d . . . .
H14 H 1.054896 0.185638 1.032852 0.046 Uiso 1 1 calc R . . .
C15 C 0.94824(14) 0.3335(2) 0.99827(18) 0.0359(5) Uani 1 1 d . . . .
H15 H 0.976584 0.376736 1.073453 0.043 Uiso 1 1 calc R . . .
C16 C 0.86027(14) 0.3843(2) 0.91252(17) 0.0286(4) Uani 1 1 d . . . .
H16 H 0.829318 0.463062 0.929281 0.034 Uiso 1 1 calc R . . .
C17 C 0.67416(13) 0.61549(18) 0.24677(15) 0.0223(4) Uani 1 1 d . . . .
C18 C 0.65575(16) 0.5389(2) 0.14557(18) 0.0360(5) Uani 1 1 d . . . .
H18 H 0.607725 0.466411 0.123502 0.043 Uiso 1 1 calc R . . .
C19 C 0.70698(18) 0.5673(3) 0.0763(2) 0.0434(6) Uani 1 1 d . . . .
H19 H 0.692494 0.515947 0.005913 0.052 Uiso 1 1 calc R . . .
C20 C 0.77904(15) 0.6699(2) 0.10920(18) 0.0348(5) Uani 1 1 d . . . .
H20 H 0.815382 0.687323 0.062887 0.042 Uiso 1 1 calc R . . .
C21 C 0.79781(14) 0.7468(2) 0.20945(17) 0.0300(4) Uani 1 1 d . . . .
H21 H 0.847099 0.817513 0.232310 0.036 Uiso 1 1 calc R . . .
C22 C 0.74502(13) 0.72105(19) 0.27685(16) 0.0256(4) Uani 1 1 d . . . .
H22 H 0.757233 0.776203 0.344724 0.031 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'
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
N1 C1 C2 106.45(14) . .
N1 C1 C10 125.67(15) . 3_666
C10 C1 C2 127.84(16) 3_666 .
C1 N1 H1 124.9 . .
C4 N1 C1 110.27(14) . .
C4 N1 H1 124.9 . .
C1 C2 H2 126.1 . .
C3 C2 C1 107.72(15) . .
C3 C2 H2 126.1 . .
C3 C2 N3 124.1(2) . .
N3 C2 C1 128.2(2) . .
C9 N2 C6 105.30(14) . .
C2 C3 H3 125.7 . .
C2 C3 C4 108.53(15) . .
C4 C3 H3 125.7 . .
C2 N3 H3A 120.0 . .
C2 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
N1 C4 C3 107.02(15) . .
N1 C4 C5 126.40(16) . .
C5 C4 C3 126.53(16) . .
C4 C5 C11 116.37(15) . .
C6 C5 C4 125.18(16) . .
C6 C5 C11 118.45(15) . .
N2 C6 C5 126.17(16) . .
N2 C6 C7 110.58(15) . .
C5 C6 C7 123.25(16) . .
C6 C7 H7 126.7 . .
C8 C7 C6 106.52(15) . .
C8 C7 H7 126.7 . .
C7 C8 H8 126.5 . .
C7 C8 C9 106.98(15) . .
C9 C8 H8 126.5 . .
N2 C9 C8 110.61(15) . .
N2 C9 C10 126.43(16) . .
C10 C9 C8 122.94(15) . .
C1 C10 C9 125.79(16) 3_666 .
C1 C10 C17 117.28(15) 3_666 .
C9 C10 C17 116.93(15) . .
C12 C11 C5 120.83(17) . .
C16 C11 C5 120.61(16) . .
C16 C11 C12 118.56(17) . .
C11 C12 H12 119.8 . .
C11 C12 C13 120.3(2) . .
C13 C12 H12 119.8 . .
C12 C13 H13 119.9 . .
C14 C13 C12 120.2(2) . .
C14 C13 H13 119.9 . .
C13 C14 H14 120.0 . .
C13 C14 C15 119.95(19) . .
C15 C14 H14 120.0 . .
C14 C15 H15 120.0 . .
C14 C15 C16 120.0(2) . .
C16 C15 H15 120.0 . .
C11 C16 H16 119.5 . .
C15 C16 C11 120.90(19) . .
C15 C16 H16 119.5 . .
C18 C17 C10 120.69(16) . .
C18 C17 C22 118.43(17) . .
C22 C17 C10 120.88(15) . .
C17 C18 H18 119.8 . .
C17 C18 C19 120.48(19) . .
C19 C18 H18 119.8 . .
C18 C19 H19 119.8 . .
C20 C19 C18 120.31(19) . .
C20 C19 H19 119.8 . .
C19 C20 H20 120.2 . .
C21 C20 C19 119.65(18) . .
C21 C20 H20 120.2 . .
C20 C21 H21 120.0 . .
C20 C21 C22 120.08(18) . .
C22 C21 H21 120.0 . .
C17 C22 H22 119.5 . .
C21 C22 C17 121.01(17) . .
C21 C22 H22 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.377(2) .
C1 C2 1.441(2) .
C1 C10 1.394(2) 3_666
N1 H1 0.8800 .
N1 C4 1.373(2) .
C2 H2 0.9500 .
C2 C3 1.366(2) .
C2 N3 1.367(3) .
N2 C6 1.373(2) .
N2 C9 1.369(2) .
C3 H3 0.9500 .
C3 C4 1.422(2) .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
C4 C5 1.403(2) .
C5 C6 1.401(2) .
C5 C11 1.496(2) .
C6 C7 1.455(2) .
C7 H7 0.9500 .
C7 C8 1.342(2) .
C8 H8 0.9500 .
C8 C9 1.452(2) .
C9 C10 1.408(2) .
C10 C17 1.495(2) .
C11 C12 1.395(3) .
C11 C16 1.390(3) .
C12 H12 0.9500 .
C12 C13 1.396(3) .
C13 H13 0.9500 .
C13 C14 1.378(3) .
C14 H14 0.9500 .
C14 C15 1.382(3) .
C15 H15 0.9500 .
C15 C16 1.389(3) .
C16 H16 0.9500 .
C17 C18 1.387(3) .
C17 C22 1.393(2) .
C18 H18 0.9500 .
C18 C19 1.388(3) .
C19 H19 0.9500 .
C19 C20 1.384(3) .
C20 H20 0.9500 .
C20 C21 1.377(3) .
C21 H21 0.9500 .
C21 C22 1.382(3) .
C22 H22 0.9500 .
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_4
C1 N1 C4 C3 0.6(2) . .
C1 N1 C4 C5 178.19(17) . .
C1 C2 C3 C4 -0.1(2) . .
C1 C10 C17 C18 -69.1(2) 3_666 .
C1 C10 C17 C22 111.67(19) 3_666 .
N1 C1 C2 C3 0.44(19) . .
N1 C1 C2 N3 -179.9(2) . .
N1 C4 C5 C6 -2.1(3) . .
N1 C4 C5 C11 177.41(17) . .
C2 C1 N1 C4 -0.62(19) . .
C2 C3 C4 N1 -0.3(2) . .
C2 C3 C4 C5 -177.90(17) . .
N2 C6 C7 C8 -0.2(2) . .
N2 C9 C10 C1 0.2(3) . 3_666
N2 C9 C10 C17 -178.76(16) . .
C3 C4 C5 C6 175.08(17) . .
C3 C4 C5 C11 -5.4(3) . .
N3 C2 C3 C4 -179.8(2) . .
C4 C5 C6 N2 0.4(3) . .
C4 C5 C6 C7 -179.09(16) . .
C4 C5 C11 C12 116.18(19) . .
C4 C5 C11 C16 -63.4(2) . .
C5 C6 C7 C8 179.28(17) . .
C5 C11 C12 C13 -179.82(17) . .
C5 C11 C16 C15 178.99(17) . .
C6 N2 C9 C8 0.39(18) . .
C6 N2 C9 C10 178.88(16) . .
C6 C5 C11 C12 -64.3(2) . .
C6 C5 C11 C16 116.1(2) . .
C6 C7 C8 C9 0.47(19) . .
C7 C8 C9 N2 -0.6(2) . .
C7 C8 C9 C10 -179.11(16) . .
C8 C9 C10 C1 178.48(16) . 3_666
C8 C9 C10 C17 -0.4(2) . .
C9 N2 C6 C5 -179.61(17) . .
C9 N2 C6 C7 -0.10(19) . .
C9 C10 C17 C18 109.9(2) . .
C9 C10 C17 C22 -69.3(2) . .
C10 C1 N1 C4 -178.54(17) 3_666 .
C10 C1 C2 C3 178.30(17) 3_666 .
C10 C1 C2 N3 -2.0(3) 3_666 .
C10 C17 C18 C19 -179.2(2) . .
C10 C17 C22 C21 177.53(17) . .
C11 C5 C6 N2 -179.16(16) . .
C11 C5 C6 C7 1.4(3) . .
C11 C12 C13 C14 0.8(3) . .
C12 C11 C16 C15 -0.6(3) . .
C12 C13 C14 C15 -0.6(3) . .
C13 C14 C15 C16 -0.2(3) . .
C14 C15 C16 C11 0.9(3) . .
C16 C11 C12 C13 -0.2(3) . .
C17 C18 C19 C20 1.8(4) . .
C18 C17 C22 C21 -1.7(3) . .
C18 C19 C20 C21 -1.9(4) . .
C19 C20 C21 C22 0.2(3) . .
C20 C21 C22 C17 1.7(3) . .
C22 C17 C18 C19 0.0(3) . .
