#------------------------------------------------------------------------------
#$Date: 2022-05-05 22:50:42 +0200 (Thu 05 de May de 2022) $
#$Revision: 275048 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/13/7061354.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_7061354
loop_
_publ_author_name
'Jing, Haoyu'
'Wang, Pengzhi'
'Chen, Boyang'
'Jiang, Jianbing'
'Vairaprakash, Pothiappan'
'Liu, Sijia'
'Rong, Jie'
'Chen, Chih-Yuan'
'Nalaoh, Phattananawee'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Synthesis of bacteriochlorins bearing diverse β-substituents
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5534
_journal_page_last               5555
_journal_paper_doi               10.1039/D1NJ05852E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C6 H6 Br N O2'
_chemical_formula_sum            'C6 H6 Br N O2'
_chemical_formula_weight         204.03
_chemical_name_common            'Spot 3'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2021-11-02 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.7683(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0877(9)
_cell_length_b                   11.2881(9)
_cell_length_c                   11.6866(10)
_cell_measurement_reflns_used    184
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      33.6074
_cell_measurement_theta_min      2.8431
_cell_volume                     1392.9(2)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16747
_diffrn_reflns_theta_full        35.06
_diffrn_reflns_theta_max         35.06
_diffrn_reflns_theta_min         2.64
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.834
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'mu from formula'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0196
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0248P)²+0.7298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0485
_reflns_number_gt                2655
_reflns_number_total             3079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05852e2.cif
_cod_data_source_block           rds778
_cod_depositor_comments
'Adding full bibliography for 7061354--7061359.cif.'
_cod_database_code               7061354
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.01953(2) 0.13543(2) 0.58486(2) 0.01547(4) Uani d . . . 1 . .
O O1 0.04578(8) 0.37383(7) 0.43444(8) 0.01421(15) Uani d . . . 1 . .
O O2 0.21145(7) 0.49732(7) 0.50250(7) 0.01364(14) Uani d . . . 1 . .
N N1 0.35826(9) 0.26404(9) 0.77729(9) 0.01356(16) Uani d . . . 1 . .
H H1 0.4296(15) 0.2562(14) 0.8326(15) 0.016 Uiso d U . . 1 . .
C C1 0.26202(11) 0.18290(10) 0.75502(10) 0.01334(18) Uani d . . . 1 . .
H H1A 0.259694 0.114045 0.801044 0.016 Uiso calc U . R 1 . .
C C2 0.16978(10) 0.21964(9) 0.65400(9) 0.01075(17) Uani d . . . 1 . .
C C3 0.21112(9) 0.32691(9) 0.61342(9) 0.00977(16) Uani d . . . 1 . .
C C4 0.32948(10) 0.35064(9) 0.69355(10) 0.01223(18) Uani d . . . 1 . .
H H4 0.381506 0.416589 0.690154 0.015 Uiso calc U . R 1 . .
C C5 0.14648(10) 0.39810(9) 0.50847(9) 0.00992(16) Uani d . . . 1 . .
C C6 0.15516(12) 0.57215(10) 0.39978(11) 0.0181(2) Uani d . . . 1 . .
H H6A 0.209651 0.64107 0.402283 0.027 Uiso calc U . R 1 . .
H H6B 0.071651 0.59883 0.401588 0.027 Uiso calc U . R 1 . .
H H6C 0.145985 0.527313 0.3258 0.027 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'
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
C5 O2 C6 . . 115.32(8) ?
C4 N1 C1 . . 110.38(9) ?
C4 N1 H1 . . 125.4(11) ?
C1 N1 H1 . . 123.9(11) ?
C2 C1 N1 . . 107.15(9) ?
C2 C1 H1A . . 126.4 ?
N1 C1 H1A . . 126.4 ?
C1 C2 C3 . . 108.22(9) ?
C1 C2 Br1 . . 123.37(8) ?
C3 C2 Br1 . . 128.39(8) ?
C4 C3 C2 . . 105.88(9) ?
C4 C3 C5 . . 125.64(10) ?
C2 C3 C5 . . 128.48(9) ?
N1 C4 C3 . . 108.38(9) ?
N1 C4 H4 . . 125.8 ?
C3 C4 H4 . . 125.8 ?
O1 C5 O2 . . 122.71(10) ?
O1 C5 C3 . . 125.63(10) ?
O2 C5 C3 . . 111.65(9) ?
O2 C6 H6A . . 109.5 ?
O2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
O2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 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 . 1.8735(10) ?
O1 C5 . 1.2168(13) ?
O2 C5 . 1.3449(13) ?
O2 C6 . 1.4445(14) ?
N1 C4 . 1.3507(14) ?
N1 C1 . 1.3696(15) ?
N1 H1 . 0.860(16) ?
C1 C2 . 1.3692(15) ?
C1 H1A . 0.95 ?
C2 C3 . 1.4262(15) ?
C3 C4 . 1.3859(14) ?
C3 C5 . 1.4585(14) ?
C4 H4 . 0.95 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
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 O1 8_556 0.860(16) 2.072(16) 2.7907(12) 140.6(14) ?
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 C2 . . . . 0.03(12) ?
N1 C1 C2 C3 . . . . -0.09(12) ?
N1 C1 C2 Br1 . . . . 178.49(8) ?
C1 C2 C3 C4 . . . . 0.12(12) ?
Br1 C2 C3 C4 . . . . -178.36(8) ?
C1 C2 C3 C5 . . . . 178.87(10) ?
Br1 C2 C3 C5 . . . . 0.38(16) ?
C1 N1 C4 C3 . . . . 0.05(13) ?
C2 C3 C4 N1 . . . . -0.10(12) ?
C5 C3 C4 N1 . . . . -178.90(10) ?
C6 O2 C5 O1 . . . . -1.67(15) ?
C6 O2 C5 C3 . . . . 178.92(9) ?
C4 C3 C5 O1 . . . . 175.68(11) ?
C2 C3 C5 O1 . . . . -2.84(18) ?
C4 C3 C5 O2 . . . . -4.93(15) ?
C2 C3 C5 O2 . . . . 176.55(10) ?
