#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:12:22 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268892 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/08/7060815.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_7060815
loop_
_publ_author_name
'Chung, Duy T. M.'
'Tran, Phuong Vy'
'Chau Nguyen, Khiem'
'Wang, Pengzhi'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Synthesis of model bacteriochlorophylls containing substituents of native
 rings A, C and E
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13302
_journal_page_last               13316
_journal_paper_doi               10.1039/D1NJ02469H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C13 H12 Br N O3 S'
_chemical_formula_sum            'C13 H12 Br N O3 S'
_chemical_formula_weight         342.21
_chemical_name_common            DC-006
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                88.161(2)
_cell_angle_beta                 88.2410(10)
_cell_angle_gamma                63.805(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3674(3)
_cell_length_b                   8.5936(3)
_cell_length_c                   10.4526(3)
_cell_measurement_reflns_used    918
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      23.6367
_cell_measurement_theta_min      2.6332
_cell_volume                     673.95(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39430
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    3.207
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.098
_refine_diff_density_max         1.894
_refine_diff_density_min         -0.624
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.6575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                3502
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02469h2.cif
_cod_data_source_block           rs030
_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 

 Adding full bibliography for 7060813--7060817.cif.
;
_cod_database_code               7060815
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
Br Br1 0.35696(3) 0.54006(3) 0.34113(2) 0.03288(9) Uani d . . . 1 . .
S S1 0.27268(7) 0.12919(6) 0.72674(5) 0.01995(11) Uani d . . . 1 . .
O O1 -0.0906(2) 0.6867(2) 0.80818(19) 0.0364(4) Uani d . . . 1 . .
O O2 0.1170(2) 0.1446(2) 0.79588(17) 0.0275(3) Uani d . . . 1 . .
O O3 0.3639(2) -0.0119(2) 0.64267(17) 0.0282(3) Uani d . . . 1 . .
N N1 0.2094(2) 0.3082(2) 0.63074(16) 0.0193(3) Uani d . . . 1 . .
C C1 0.3076(3) 0.3040(3) 0.5208(2) 0.0214(4) Uani d . . . 1 . .
H H1 0.388402 0.203095 0.477573 0.026 Uiso calc U . R 1 . .
C C2 0.2669(3) 0.4711(3) 0.4861(2) 0.0227(4) Uani d . . . 1 . .
C C3 0.1453(3) 0.5855(3) 0.5764(2) 0.0220(4) Uani d . . . 1 . .
C C4 0.1124(3) 0.4822(3) 0.6675(2) 0.0203(4) Uani d . . . 1 . .
C C5 -0.0085(3) 0.5359(3) 0.7778(2) 0.0261(4) Uani d . . . 1 . .
H H5 -0.024014 0.449498 0.828344 0.031 Uiso calc U . R 1 . .
C C6 0.0711(4) 0.7788(3) 0.5702(3) 0.0324(5) Uani d . . . 1 . .
H H6A -0.042608 0.829916 0.617699 0.049 Uiso calc U . R 1 . .
H H6B 0.052063 0.818908 0.480663 0.049 Uiso calc U . R 1 . .
H H6C 0.155142 0.814361 0.608235 0.049 Uiso calc U . R 1 . .
C C7 0.4218(3) 0.1499(3) 0.8304(2) 0.0199(4) Uani d . . . 1 . .
C C8 0.5969(3) 0.0991(3) 0.7883(2) 0.0253(4) Uani d . . . 1 . .
H H8 0.637117 0.045376 0.707923 0.03 Uiso calc U . R 1 . .
C C9 0.7111(3) 0.1288(3) 0.8666(2) 0.0281(5) Uani d . . . 1 . .
H H9 0.831433 0.093607 0.839771 0.034 Uiso calc U . R 1 . .
C C10 0.6524(3) 0.2092(3) 0.9836(2) 0.0276(5) Uani d . . . 1 . .
C C11 0.4774(3) 0.2522(3) 1.0251(2) 0.0273(4) Uani d . . . 1 . .
H H11 0.437993 0.302226 1.106683 0.033 Uiso calc U . R 1 . .
C C12 0.3610(3) 0.2230(3) 0.9493(2) 0.0230(4) Uani d . . . 1 . .
H H12 0.242535 0.25221 0.97793 0.028 Uiso calc U . R 1 . .
C C13 0.7742(4) 0.2510(4) 1.0643(3) 0.0388(6) Uani d . . . 1 . .
H H13A 0.747376 0.240104 1.155115 0.058 Uiso calc U . R 1 . .
H H13B 0.756031 0.369979 1.044932 0.058 Uiso calc U . R 1 . .
H H13C 0.898319 0.170162 1.045215 0.058 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 0.0033 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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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
O2 S1 O3 . . 120.36(10) ?
O2 S1 N1 . . 106.55(9) ?
O3 S1 N1 . . 104.36(10) ?
O2 S1 C7 . . 110.09(10) ?
O3 S1 C7 . . 110.64(10) ?
N1 S1 C7 . . 103.20(9) ?
C1 N1 C4 . . 108.66(17) ?
C1 N1 S1 . . 119.87(15) ?
C4 N1 S1 . . 126.88(15) ?
C2 C1 N1 . . 107.37(19) ?
C2 C1 H1 . . 126.3 ?
N1 C1 H1 . . 126.3 ?
C1 C2 C3 . . 109.88(19) ?
C1 C2 Br1 . . 125.20(17) ?
C3 C2 Br1 . . 124.92(16) ?
C4 C3 C2 . . 106.31(18) ?
C4 C3 C6 . . 128.5(2) ?
C2 C3 C6 . . 125.2(2) ?
C3 C4 N1 . . 107.70(18) ?
C3 C4 C5 . . 128.4(2) ?
N1 C4 C5 . . 123.81(19) ?
O1 C5 C4 . . 122.8(2) ?
O1 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C12 C7 C8 . . 122.1(2) ?
C12 C7 S1 . . 119.34(16) ?
C8 C7 S1 . . 118.53(17) ?
C9 C8 C7 . . 118.4(2) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C8 C9 C10 . . 121.0(2) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.9(2) ?
C9 C10 C13 . . 120.7(2) ?
C11 C10 C13 . . 120.4(2) ?
C12 C11 C10 . . 121.2(2) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C7 . . 118.3(2) ?
C11 C12 H12 . . 120.8 ?
C7 C12 H12 . . 120.8 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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
Br1 C2 . 1.866(2) ?
S1 O2 . 1.4259(16) ?
S1 O3 . 1.4267(16) ?
S1 N1 . 1.6935(18) ?
S1 C7 . 1.748(2) ?
O1 C5 . 1.216(3) ?
N1 C1 . 1.383(3) ?
N1 C4 . 1.411(3) ?
C1 C2 . 1.361(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.418(3) ?
C3 C4 . 1.384(3) ?
C3 C6 . 1.495(3) ?
C4 C5 . 1.455(3) ?
C5 H5 . 0.95 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C12 . 1.388(3) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.388(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.391(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.400(3) ?
C10 C13 . 1.508(3) ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
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
O2 S1 N1 C1 . . . . -155.99(16) ?
O3 S1 N1 C1 . . . . -27.65(18) ?
C7 S1 N1 C1 . . . . 88.06(17) ?
O2 S1 N1 C4 . . . . 50.88(19) ?
O3 S1 N1 C4 . . . . 179.22(17) ?
C7 S1 N1 C4 . . . . -65.07(18) ?
C4 N1 C1 C2 . . . . -2.7(2) ?
S1 N1 C1 C2 . . . . -160.30(15) ?
N1 C1 C2 C3 . . . . 1.8(2) ?
N1 C1 C2 Br1 . . . . -177.96(14) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
Br1 C2 C3 C4 . . . . 179.57(15) ?
C1 C2 C3 C6 . . . . 179.8(2) ?
Br1 C2 C3 C6 . . . . -0.4(3) ?
C2 C3 C4 N1 . . . . -1.4(2) ?
C6 C3 C4 N1 . . . . 178.5(2) ?
C2 C3 C4 C5 . . . . -177.3(2) ?
C6 C3 C4 C5 . . . . 2.7(4) ?
C1 N1 C4 C3 . . . . 2.6(2) ?
S1 N1 C4 C3 . . . . 158.16(15) ?
C1 N1 C4 C5 . . . . 178.70(19) ?
S1 N1 C4 C5 . . . . -25.7(3) ?
C3 C4 C5 O1 . . . . -5.0(4) ?
N1 C4 C5 O1 . . . . 179.8(2) ?
O2 S1 C7 C12 . . . . -17.5(2) ?
O3 S1 C7 C12 . . . . -152.97(17) ?
N1 S1 C7 C12 . . . . 95.89(17) ?
O2 S1 C7 C8 . . . . 165.22(17) ?
O3 S1 C7 C8 . . . . 29.8(2) ?
N1 S1 C7 C8 . . . . -81.37(18) ?
C12 C7 C8 C9 . . . . -2.4(3) ?
S1 C7 C8 C9 . . . . 174.82(17) ?
C7 C8 C9 C10 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 3.3(3) ?
C8 C9 C10 C13 . . . . -176.2(2) ?
C9 C10 C11 C12 . . . . -2.9(3) ?
C13 C10 C11 C12 . . . . 176.6(2) ?
C10 C11 C12 C7 . . . . -0.1(3) ?
C8 C7 C12 C11 . . . . 2.8(3) ?
S1 C7 C12 C11 . . . . -174.38(16) ?
