#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:03:15 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282301 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568542.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_1568542
loop_
_publ_author_name
'Ji, Peng'
'Meng, Xiang'
'Chen, Jing'
'Gao, Feng'
'Xu, Hang'
'Wang, Wei'
_publ_section_title
;
 Combining photoredox catalysis and hydrogen atom transfer for dearomative
 functionalization of electron rich heteroarenes.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3332
_journal_page_last               3337
_journal_paper_doi               10.1039/d3sc00060e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C8 H9 Br N2 O2'
_chemical_formula_sum            'C8 H9 Br N2 O2'
_chemical_formula_weight         245.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2630(13)
_cell_length_b                   24.954(2)
_cell_length_c                   5.6399(5)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.89
_cell_volume                     1866.6(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.632
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.372
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.6717.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0185
_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)+(0.0244P)²+1.3127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1743
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00060e2.cif
_cod_data_source_block           mo_220822peng_0ma
_cod_depositor_comments          'Adding full bibliography for 1568542.cif.'
_cod_database_code               1568542
_shelx_shelxl_version_number     2016/6
_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   0.811
_shelx_estimated_absorpt_t_min   0.274
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3B,H3A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35984(2) 0.70010(2) -0.11847(3) 0.01781(7) Uani 1 1 d . . . . .
O1 O 0.38383(9) 0.32447(5) 0.5371(2) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.34373(8) 0.40060(5) 0.7275(2) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.37078(9) 0.55118(6) 0.1510(2) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.38917(10) 0.57828(6) 0.3556(2) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.39531(11) 0.46430(6) 0.3285(3) 0.0153(3) Uani 1 1 d . . . . .
H4 H 0.412315 0.481467 0.473385 0.018 Uiso 1 1 calc R U . . .
C3 C 0.39858(12) 0.40419(6) 0.3180(3) 0.0157(3) Uani 1 1 d . . . . .
H3B H 0.467279 0.392727 0.271742 0.019 Uiso 1 1 calc R U . . .
H3A H 0.351287 0.391629 0.194122 0.019 Uiso 1 1 calc R U . . .
C6 C 0.35769(11) 0.58440(7) -0.0372(3) 0.0144(3) Uani 1 1 d . . . . .
H6 H 0.344066 0.574399 -0.196536 0.017 Uiso 1 1 calc R U . . .
C7 C 0.36823(11) 0.63539(6) 0.0503(3) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.36996(11) 0.49425(7) 0.1461(3) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.350064 0.476914 0.003601 0.019 Uiso 1 1 calc R U . . .
C2 C 0.37129(11) 0.37815(7) 0.5508(3) 0.0144(3) Uani 1 1 d . . . . .
C8 C 0.38721(12) 0.62978(7) 0.2930(3) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.397365 0.658830 0.399250 0.020 Uiso 1 1 calc R U . . .
C1 C 0.36878(13) 0.29621(7) 0.7582(3) 0.0233(4) Uani 1 1 d . . . . .
H1A H 0.382810 0.258013 0.735071 0.035 Uiso 1 1 calc R U . . .
H1B H 0.298851 0.300798 0.810537 0.035 Uiso 1 1 calc R U . . .
H1C H 0.414483 0.310683 0.878803 0.035 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 114.65(13) . . ?
N2 N1 C5 121.00(13) . . ?
C6 N1 N2 112.50(13) . . ?
C6 N1 C5 126.46(14) . . ?
C8 N2 N1 104.56(13) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C5 C4 C3 122.98(15) . . ?
C4 C3 H3B 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 C2 112.90(14) . . ?
H3B C3 H3A 107.8 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N1 C6 H6 127.1 . . ?
N1 C6 C7 105.79(14) . . ?
C7 C6 H6 127.1 . . ?
C6 C7 Br1 127.53(13) . . ?
C6 C7 C8 106.11(15) . . ?
C8 C7 Br1 126.36(13) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 N1 123.44(15) . . ?
C4 C5 H5 118.3 . . ?
O1 C2 C3 110.35(14) . . ?
O2 C2 O1 123.17(16) . . ?
O2 C2 C3 126.47(15) . . ?
N2 C8 C7 111.05(15) . . ?
N2 C8 H8 124.5 . . ?
C7 C8 H8 124.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.8778(16) . ?
O1 C2 1.3519(19) . ?
O1 C1 1.446(2) . ?
O2 C2 1.200(2) . ?
N1 N2 1.3597(18) . ?
N1 C6 1.358(2) . ?
N1 C5 1.421(2) . ?
N2 C8 1.333(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.502(2) . ?
C4 C5 1.315(2) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 C2 1.509(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(2) . ?
C7 C8 1.399(2) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 N2 -179.38(11) . . . . ?
N1 N2 C8 C7 -0.30(18) . . . . ?
N1 C6 C7 Br1 179.49(10) . . . . ?
N1 C6 C7 C8 -0.21(16) . . . . ?
N2 N1 C6 C7 0.04(17) . . . . ?
N2 N1 C5 C4 -6.3(2) . . . . ?
C4 C3 C2 O1 -174.75(12) . . . . ?
C4 C3 C2 O2 4.1(2) . . . . ?
C3 C4 C5 N1 -177.21(14) . . . . ?
C6 N1 N2 C8 0.16(17) . . . . ?
C6 N1 C5 C4 171.33(15) . . . . ?
C6 C7 C8 N2 0.33(18) . . . . ?
C5 N1 N2 C8 178.12(13) . . . . ?
C5 N1 C6 C7 -177.78(13) . . . . ?
C5 C4 C3 C2 -147.55(15) . . . . ?
C1 O1 C2 O2 -4.5(2) . . . . ?
C1 O1 C2 C3 174.43(12) . . . . ?
