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#$Date: 2022-05-11 03:35:36 +0300 (Wed, 11 May 2022) $
#$Revision: 275316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158690.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_7158690
loop_
_publ_author_name
'Zhaojiang, Shi'
'Li, Nan'
'Wang, Wei-Zhen'
'Lu, Hao-Kuan'
'Yuan, Yaofeng'
'Li, Zhen'
'Ye, Ke-Yin'
_publ_section_title
;
 Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward
 3-hydroxyisoindolinone derivatives
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00637E
_journal_year                    2022
_chemical_formula_moiety         'C15 H11 Br O3'
_chemical_formula_sum            'C15 H11 Br O3'
_chemical_formula_weight         319.15
_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
_audit_creation_date             2021-09-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                91.227(3)
_cell_angle_beta                 91.751(3)
_cell_angle_gamma                113.005(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8870(4)
_cell_length_b                   8.0452(6)
_cell_length_c                   12.4860(10)
_cell_measurement_reflns_used    5433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.006
_cell_measurement_theta_min      3.150
_cell_volume                     636.08(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0685
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.316
_diffrn_reflns_theta_min         2.752
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.231
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1646 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.6048.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0467
_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)+(0.0464P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00637e2.cif
_cod_data_source_block           ln-22n-1
_cod_database_code               7158690
_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   0.738
_shelx_estimated_absorpt_t_min   0.564
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H008), C8(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H00A), C12(H00C), C3(H00D), C14(H00F), C15(H00G), C11(H00H), C5(H00I),
 C4(H00J)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H003)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 -0.27934(5) 0.27340(4) 1.03248(2) 0.05324(14) Uani 1 1 d . . . . .
O2 O 0.3663(3) 0.1858(2) 0.50404(13) 0.0298(4) Uani 1 1 d . . . . .
O3 O 0.3089(3) 0.0077(2) 0.69427(14) 0.0318(4) Uani 1 1 d . . . . .
H003 H 0.317733 -0.066246 0.650530 0.048 Uiso 1 1 calc R U . . .
O1 O 0.6998(3) 0.2440(2) 0.45962(15) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.0496(3) 0.1134(3) 0.75039(18) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.6247(4) 0.4075(3) 0.60614(19) 0.0267(5) Uani 1 1 d . . . . .
C7 C 0.4349(4) 0.3921(3) 0.64760(19) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.1570(4) 0.0702(3) 0.65717(18) 0.0241(5) Uani 1 1 d . . . . .
H008 H 0.051128 -0.025000 0.611690 0.029 Uiso 1 1 calc R U . . .
C1 C 0.5779(4) 0.2747(3) 0.51658(19) 0.0286(5) Uani 1 1 d . . . . .
C6 C 0.4335(4) 0.5090(3) 0.7311(2) 0.0299(5) Uani 1 1 d . . . . .
H00A H 0.307474 0.503628 0.758821 0.036 Uiso 1 1 calc R U . . .
C13 C -0.1460(4) 0.2080(3) 0.9178(2) 0.0303(5) Uani 1 1 d . . . . .
C12 C 0.0464(4) 0.1952(4) 0.9368(2) 0.0346(6) Uani 1 1 d . . . . .
H00C H 0.110548 0.218848 1.005201 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8177(4) 0.5310(3) 0.6460(2) 0.0321(6) Uani 1 1 d . . . . .
H00D H 0.943376 0.538387 0.616989 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2612(4) 0.2386(3) 0.58989(18) 0.0263(5) Uani 1 1 d . . . . .
H00E H 0.154239 0.278855 0.560126 0.032 Uiso 1 1 calc R U . . .
C14 C -0.2432(4) 0.1724(3) 0.8179(2) 0.0336(6) Uani 1 1 d . . . . .
H00F H -0.373453 0.179977 0.806229 0.040 Uiso 1 1 calc R U . . .
C15 C -0.1451(4) 0.1250(3) 0.7345(2) 0.0289(5) Uani 1 1 d . . . . .
H00G H -0.210760 0.100449 0.666433 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1416(4) 0.1470(3) 0.8532(2) 0.0305(5) Uani 1 1 d . . . . .
H00H H 0.270100 0.136664 0.865920 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6259(4) 0.6334(3) 0.7714(2) 0.0361(6) Uani 1 1 d . . . . .
H00I H 0.628296 0.712752 0.827183 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8157(4) 0.6432(3) 0.7310(2) 0.0349(6) Uani 1 1 d . . . . .
H00J H 0.942557 0.726001 0.761466 0.042 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'
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
C1 O2 C8 110.36(18) . . ?
C9 O3 H003 109.5 . . ?
C15 C10 C9 120.0(2) . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C15 118.1(2) . . ?
C7 C2 C1 107.7(2) . . ?
C3 C2 C7 123.1(2) . . ?
C3 C2 C1 129.2(2) . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 C8 108.6(2) . . ?
C6 C7 C8 131.8(2) . . ?
O3 C9 C10 109.89(18) . . ?
O3 C9 H008 108.8 . . ?
O3 C9 C8 110.03(19) . . ?
C10 C9 H008 108.8 . . ?
C10 C9 C8 110.59(18) . . ?
C8 C9 H008 108.8 . . ?
O2 C1 C2 108.78(19) . . ?
O1 C1 O2 122.6(2) . . ?
O1 C1 C2 128.6(2) . . ?
C7 C6 H00A 121.1 . . ?
C5 C6 C7 117.7(2) . . ?
C5 C6 H00A 121.1 . . ?
C12 C13 Br1 119.5(2) . . ?
C14 C13 Br1 119.31(18) . . ?
C14 C13 C12 121.2(2) . . ?
C13 C12 H00C 120.4 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H00C 120.4 . . ?
C2 C3 H00D 121.5 . . ?
C2 C3 C4 117.1(2) . . ?
C4 C3 H00D 121.5 . . ?
O2 C8 C7 103.92(18) . . ?
O2 C8 C9 106.70(17) . . ?
O2 C8 H00E 110.4 . . ?
C7 C8 C9 114.68(19) . . ?
C7 C8 H00E 110.4 . . ?
C9 C8 H00E 110.4 . . ?
C13 C14 H00F 120.5 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H00F 120.5 . . ?
C10 C15 H00G 119.4 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H00G 119.4 . . ?
C10 C11 H00H 119.4 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H00H 119.4 . . ?
C6 C5 H00I 119.0 . . ?
C6 C5 C4 121.9(2) . . ?
C4 C5 H00I 119.0 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H00J 119.7 . . ?
C5 C4 H00J 119.7 . . ?
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 C13 1.896(2) . ?
O2 C1 1.351(3) . ?
O2 C8 1.457(3) . ?
O3 H003 0.8200 . ?
O3 C9 1.397(3) . ?
O1 C1 1.210(3) . ?
C10 C9 1.503(3) . ?
C10 C15 1.388(3) . ?
C10 C11 1.387(3) . ?
C2 C7 1.381(3) . ?
C2 C1 1.468(3) . ?
C2 C3 1.381(4) . ?
C7 C6 1.392(3) . ?
C7 C8 1.493(3) . ?
C9 H008 0.9800 . ?
C9 C8 1.543(3) . ?
C6 H00A 0.9300 . ?
C6 C5 1.383(4) . ?
C13 C12 1.382(4) . ?
C13 C14 1.367(4) . ?
C12 H00C 0.9300 . ?
C12 C11 1.376(3) . ?
C3 H00D 0.9300 . ?
C3 C4 1.382(4) . ?
C8 H00E 0.9800 . ?
C14 H00F 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H00G 0.9300 . ?
C11 H00H 0.9300 . ?
C5 H00I 0.9300 . ?
C5 C4 1.390(4) . ?
C4 H00J 0.9300 . ?
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 C13 C12 C11 179.7(2) . . . . ?
Br1 C13 C14 C15 179.92(18) . . . . ?
O3 C9 C8 O2 56.6(2) . . . . ?
O3 C9 C8 C7 -57.8(2) . . . . ?
C10 C9 C8 O2 178.23(18) . . . . ?
C10 C9 C8 C7 63.8(2) . . . . ?
C2 C7 C6 C5 -2.0(3) . . . . ?
C2 C7 C8 O2 -7.2(2) . . . . ?
C2 C7 C8 C9 108.8(2) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C7 C2 C1 O2 1.2(2) . . . . ?
C7 C2 C1 O1 -179.4(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C7 C6 C5 C4 0.0(4) . . . . ?
C9 C10 C15 C14 -177.1(2) . . . . ?
C9 C10 C11 C12 176.7(2) . . . . ?
C1 O2 C8 C7 8.1(2) . . . . ?
C1 O2 C8 C9 -113.44(19) . . . . ?
C1 C2 C7 C6 -177.2(2) . . . . ?
C1 C2 C7 C8 3.9(2) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C6 C7 C8 O2 174.1(2) . . . . ?
C6 C7 C8 C9 -69.8(3) . . . . ?
C6 C5 C4 C3 2.0(4) . . . . ?
C13 C12 C11 C10 0.8(4) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C3 C2 C7 C6 2.3(3) . . . . ?
C3 C2 C7 C8 -176.6(2) . . . . ?
C3 C2 C1 O2 -178.2(2) . . . . ?
C3 C2 C1 O1 1.1(4) . . . . ?
C8 O2 C1 O1 174.6(2) . . . . ?
C8 O2 C1 C2 -6.0(2) . . . . ?
C8 C7 C6 C5 176.5(2) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C15 C10 C9 O3 -160.6(2) . . . . ?
C15 C10 C9 C8 77.7(3) . . . . ?
C15 C10 C11 C12 -1.7(4) . . . . ?
C11 C10 C9 O3 21.0(3) . . . . ?
C11 C10 C9 C8 -100.7(2) . . . . ?
C11 C10 C15 C14 1.4(3) . . . . ?
