#------------------------------------------------------------------------------
#$Date: 2025-08-04 09:03:09 +0200 (Mon 04 de Aug de 2025) $
#$Revision: 301442 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/13/7061368.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_7061368
loop_
_publ_author_name
'Jing, Haoyu'
'Liu, Sijia'
'Jiang, Jianbing'
'Tran, Vy-Phuong'
'Rong, Jie'
'Wang, Pengzhi'
'Lindsey, Jonathan S.'
_publ_section_title
;
   Meso bromination and derivatization of synthetic
 bacteriochlorins
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5556
_journal_page_last               5572
_journal_paper_doi               10.1039/D1NJ05853C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C36 H34 N4'
_chemical_formula_sum            'C36 H34 N4'
_chemical_formula_weight         522.67
_chemical_name_common            VP-17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                106.0936(6)
_cell_angle_beta                 105.0837(6)
_cell_angle_gamma                98.5367(6)
_cell_formula_units_Z            1
_cell_length_a                   6.95760(10)
_cell_length_b                   8.7932(2)
_cell_length_c                   12.4732(2)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      72.1029
_cell_measurement_theta_min      5.3905
_cell_volume                     687.64(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18219
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         72.10
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.225
_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     186
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0349
_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)+(0.0382P)²+0.2881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2619
_reflns_number_total             2709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05853c2.cif
_cod_data_source_block           rs144
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7061368
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.15101(13) 0.31534(11) 0.49819(7) 0.01647(19) Uani d . . . 1 . .
H H1 1.099(2) 0.4034(17) 0.5075(11) 0.02 Uiso d U . . 1 . .
N N2 0.72819(13) 0.35536(10) 0.35953(7) 0.01665(19) Uani d . . . 1 . .
C C1 1.33995(15) 0.31599(13) 0.56893(9) 0.0171(2) Uani d . . . 1 . .
C C2 1.36589(17) 0.15481(13) 0.53086(9) 0.0212(2) Uani d . . . 1 . .
H H2 1.482619 0.118108 0.562701 0.025 Uiso calc U . R 1 . .
C C3 1.19367(17) 0.06129(13) 0.44034(10) 0.0227(2) Uani d . . . 1 . .
H H3 1.170734 -0.051337 0.398375 0.027 Uiso calc U . R 1 . .
C C4 1.05538(16) 0.16135(13) 0.41993(9) 0.0187(2) Uani d . . . 1 . .
C C5 0.85933(16) 0.10898(13) 0.33811(9) 0.0196(2) Uani d . . . 1 . .
H H5 0.820537 -0.003826 0.29355 0.023 Uiso calc U . R 1 . .
C C6 0.71161(16) 0.19419(12) 0.31100(9) 0.0180(2) Uani d . . . 1 . .
C C7 0.50373(16) 0.11061(13) 0.22142(9) 0.0215(2) Uani d . . . 1 . .
H H7A 0.411905 0.056646 0.255658 0.026 Uiso calc U . R 1 . .
H H7B 0.514511 0.02872 0.15188 0.026 Uiso calc U . R 1 . .
C C8 0.42716(16) 0.25160(13) 0.18905(9) 0.0188(2) Uani d . . . 1 . .
C C9 0.55849(15) 0.39470(12) 0.30099(9) 0.0161(2) Uani d . . . 1 . .
C C10 0.52496(15) 0.55126(13) 0.33534(9) 0.0165(2) Uani d . . . 1 . .
C C11 0.19355(16) 0.22003(14) 0.15635(10) 0.0244(2) Uani d . . . 1 . .
H H11A 0.131155 0.112471 0.096272 0.037 Uiso calc U . R 1 . .
H H11B 0.146975 0.303846 0.125426 0.037 Uiso calc U . R 1 . .
H H11C 0.152978 0.223574 0.226417 0.037 Uiso calc U . R 1 . .
C C12 0.49618(18) 0.27436(14) 0.08562(9) 0.0242(2) Uani d . . . 1 . .
H H12A 0.644585 0.285762 0.105108 0.036 Uiso calc U . R 1 . .
H H12B 0.462142 0.372515 0.070932 0.036 Uiso calc U . R 1 . .
H H12C 0.425729 0.179277 0.015006 0.036 Uiso calc U . R 1 . .
C C13 0.33945(15) 0.59332(12) 0.26845(9) 0.0168(2) Uani d . . . 1 . .
C C14 0.16189(16) 0.58158(13) 0.30091(9) 0.0210(2) Uani d . . . 1 . .
H H14 0.157507 0.544648 0.36515 0.025 Uiso calc U . R 1 . .
C C15 -0.00854(16) 0.62333(13) 0.24028(10) 0.0221(2) Uani d . . . 1 . .
H H15 -0.129041 0.613794 0.262712 0.027 Uiso calc U . R 1 . .
C C16 -0.00329(16) 0.67884(13) 0.14720(9) 0.0216(2) Uani d . . . 1 . .
H H16 -0.120343 0.706437 0.105329 0.026 Uiso calc U . R 1 . .
C C17 0.17363(17) 0.69398(14) 0.11534(9) 0.0223(2) Uani d . . . 1 . .
H H17 0.178165 0.733038 0.052036 0.027 Uiso calc U . R 1 . .
C C18 0.34379(16) 0.65219(13) 0.17576(9) 0.0195(2) Uani d . . . 1 . .
H H18 0.464721 0.663733 0.153861 0.023 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C1 . . 110.37(9) ?
C4 N1 H1 . . 126.8(8) ?
C1 N1 H1 . . 122.7(8) ?
C6 N2 C9 . . 108.70(8) ?
N1 C1 C10 . 2_766 126.49(9) ?
N1 C1 C2 . . 106.49(9) ?
C10 C1 C2 2_766 . 126.92(10) ?
C3 C2 C1 . . 108.24(9) ?
C3 C2 H2 . . 125.9 ?
C1 C2 H2 . . 125.9 ?
C2 C3 C4 . . 108.33(10) ?
C2 C3 H3 . . 125.8 ?
C4 C3 H3 . . 125.8 ?
N1 C4 C5 . . 127.88(9) ?
N1 C4 C3 . . 106.53(9) ?
C5 C4 C3 . . 125.56(10) ?
C6 C5 C4 . . 130.69(10) ?
C6 C5 H5 . . 114.7 ?
C4 C5 H5 . . 114.7 ?
N2 C6 C5 . . 126.76(10) ?
N2 C6 C7 . . 111.44(9) ?
C5 C6 C7 . . 121.79(9) ?
C6 C7 C8 . . 102.86(8) ?
C6 C7 H7A . . 111.2 ?
C8 C7 H7A . . 111.2 ?
C6 C7 H7B . . 111.2 ?
C8 C7 H7B . . 111.2 ?
H7A C7 H7B . . 109.1 ?
C11 C8 C7 . . 111.14(9) ?
C11 C8 C12 . . 110.17(9) ?
C7 C8 C12 . . 109.26(9) ?
C11 C8 C9 . . 118.41(9) ?
C7 C8 C9 . . 99.52(8) ?
C12 C8 C9 . . 107.67(8) ?
N2 C9 C10 . . 122.25(9) ?
N2 C9 C8 . . 111.32(8) ?
C10 C9 C8 . . 126.17(9) ?
C9 C10 C1 . 2_766 124.66(9) ?
C9 C10 C13 . . 121.54(9) ?
C1 C10 C13 2_766 . 113.77(9) ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 118.49(9) ?
C14 C13 C10 . . 120.71(9) ?
C18 C13 C10 . . 120.73(9) ?
C15 C14 C13 . . 120.69(10) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.18(10) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 119.75(10) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C17 C16 . . 120.10(10) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C13 . . 120.77(10) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.3750(13) ?
N1 C1 . 1.3777(13) ?
N1 H1 . 0.894(14) ?
N2 C6 . 1.3520(13) ?
N2 C9 . 1.3636(13) ?
C1 C10 2_766 1.4103(15) ?
C1 C2 . 1.4192(14) ?
C2 C3 . 1.3694(16) ?
C2 H2 . 0.95 ?
C3 C4 . 1.4187(15) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3938(15) ?
C5 C6 . 1.3857(15) ?
C5 H5 . 0.95 ?
C6 C7 . 1.5061(14) ?
C7 C8 . 1.5314(14) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C11 . 1.5308(14) ?
C8 C12 . 1.5402(15) ?
C8 C9 . 1.5454(14) ?
C9 C10 . 1.3978(14) ?
C10 C13 . 1.5003(13) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.3951(14) ?
C13 C18 . 1.3967(14) ?
C14 C15 . 1.3890(15) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3850(16) ?
C15 H15 . 0.95 ?
C16 C17 . 1.3878(16) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3868(15) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . 0.894(14) 2.647(13) 3.1251(12) 114.4(10) ?
N1 H1 N2 2_766 0.894(14) 2.225(13) 2.8094(12) 122.6(10) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . 2_766 -175.11(10) ?
C4 N1 C1 C2 . . . . 1.52(11) ?
N1 C1 C2 C3 . . . . -0.73(12) ?
C10 C1 C2 C3 2_766 . . . 175.89(10) ?
C1 C2 C3 C4 . . . . -0.30(13) ?
C1 N1 C4 C5 . . . . 176.56(10) ?
C1 N1 C4 C3 . . . . -1.70(11) ?
C2 C3 C4 N1 . . . . 1.21(12) ?
C2 C3 C4 C5 . . . . -177.10(10) ?
N1 C4 C5 C6 . . . . 1.69(19) ?
C3 C4 C5 C6 . . . . 179.63(11) ?
C9 N2 C6 C5 . . . . 173.95(10) ?
C9 N2 C6 C7 . . . . -7.37(11) ?
C4 C5 C6 N2 . . . . 1.10(19) ?
C4 C5 C6 C7 . . . . -177.46(11) ?
N2 C6 C7 C8 . . . . 20.74(11) ?
C5 C6 C7 C8 . . . . -160.50(10) ?
C6 C7 C8 C11 . . . . -148.80(9) ?
C6 C7 C8 C12 . . . . 89.41(10) ?
C6 C7 C8 C9 . . . . -23.21(10) ?
C6 N2 C9 C10 . . . . 176.08(9) ?
C6 N2 C9 C8 . . . . -9.53(11) ?
C11 C8 C9 N2 . . . . 141.76(9) ?
C7 C8 C9 N2 . . . . 21.34(10) ?
C12 C8 C9 N2 . . . . -92.52(10) ?
C11 C8 C9 C10 . . . . -44.12(15) ?
C7 C8 C9 C10 . . . . -164.55(10) ?
C12 C8 C9 C10 . . . . 81.60(12) ?
N2 C9 C10 C1 . . . 2_766 0.80(16) ?
C8 C9 C10 C1 . . . 2_766 -172.72(9) ?
N2 C9 C10 C13 . . . . 178.74(9) ?
C8 C9 C10 C13 . . . . 5.22(15) ?
C9 C10 C13 C14 . . . . 92.71(12) ?
C1 C10 C13 C14 2_766 . . . -89.13(12) ?
C9 C10 C13 C18 . . . . -90.25(13) ?
C1 C10 C13 C18 2_766 . . . 87.91(12) ?
C18 C13 C14 C15 . . . . 1.73(16) ?
C10 C13 C14 C15 . . . . 178.83(10) ?
C13 C14 C15 C16 . . . . -0.63(17) ?
C14 C15 C16 C17 . . . . -0.57(16) ?
C15 C16 C17 C18 . . . . 0.62(16) ?
C16 C17 C18 C13 . . . . 0.52(16) ?
C14 C13 C18 C17 . . . . -1.67(16) ?
C10 C13 C18 C17 . . . . -178.78(10) ?
