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#$Date: 2025-03-04 20:29:02 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/41/7134193.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_7134193
loop_
_publ_author_name
'Wang, Jingjing'
'Qin, Yuran'
'Cui, Ke'
'Li, Xueqi'
'Cui, Mingyue'
'Cao, Sheng'
'Zhang, Linbo'
'Shen, Qin'
'Wang, Teng'
'Li, Feng'
_publ_section_title
;
 Solvent-controlled silver catalyzed radical transformation of
 α-imino-oxy acids with cyclic aldimines.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3359
_journal_page_last               3362
_journal_paper_doi               10.1039/d4cc05675b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C11 H9 Br N O2'
_chemical_formula_weight         267.10
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-06 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                82.509(18)
_cell_angle_beta                 89.624(18)
_cell_angle_gamma                84.148(19)
_cell_formula_units_Z            2
_cell_length_a                   6.7614(19)
_cell_length_b                   7.298(2)
_cell_length_c                   11.361(3)
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.83
_cell_volume                     552.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0759
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16439
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         2.830
_exptl_absorpt_coefficient_mu    3.695
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0431
_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)+(0.0314P)²+0.5390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2529
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05675b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7134193--7134194.cif.'
_cod_database_code               7134193
_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_min   0.392
_shelx_estimated_absorpt_t_max   0.785
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 0.77893(7) 0.55971(6) 0.71673(3) 0.06707(18) Uani 1 1 d . . . . .
O1 O 0.1637(3) 0.9340(3) 0.3617(2) 0.0569(6) Uani 1 1 d . . . . .
O2 O 0.4318(4) 0.9349(4) 0.2045(2) 0.0575(6) Uani 1 1 d . . . . .
N1 N 0.7906(6) 0.3838(5) 0.0696(3) 0.0769(10) Uani 1 1 d . . . . .
C1 C 0.7495(6) 0.5378(6) 0.0481(3) 0.0596(10) Uani 1 1 d . . . . .
C2 C 0.6953(8) 0.7370(6) 0.0239(3) 0.0715(12) Uani 1 1 d . . . . .
H2 H 0.552814 0.762605 0.032941 0.086 Uiso 1 1 calc R U . . .
H3 H 0.727844 0.779406 -0.057747 0.086 Uiso 1 1 calc R U . . .
C3 C 0.8007(7) 0.8448(5) 0.1055(3) 0.0625(10) Uani 1 1 d . . . . .
H4 H 0.759732 0.976164 0.084226 0.075 Uiso 1 1 calc R U . . .
H5 H 0.942661 0.825214 0.092020 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7619(5) 0.7928(5) 0.2371(3) 0.0463(8) Uani 1 1 d . . . . .
H6 H 0.789120 0.659221 0.256372 0.056 Uiso 1 1 calc R U . . .
H7 H 0.854652 0.849732 0.282127 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5547(5) 0.8495(4) 0.2763(3) 0.0390(7) Uani 1 1 d . . . . .
C6 C 0.5008(4) 0.8022(4) 0.4016(3) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.3038(4) 0.8467(4) 0.4385(3) 0.0399(7) Uani 1 1 d . . . . .
C8 C 0.2533(5) 0.8017(5) 0.5562(3) 0.0491(8) Uani 1 1 d . . . . .
H8 H 0.122983 0.829132 0.579972 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3921(6) 0.7175(4) 0.6379(3) 0.0507(8) Uani 1 1 d . . . . .
H1 H 0.356735 0.689161 0.716926 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5869(5) 0.6742(4) 0.6022(3) 0.0425(7) Uani 1 1 d . . . . .
C11 C 0.6406(4) 0.7143(4) 0.4863(3) 0.0376(6) Uani 1 1 d . . . . .
H9 H 0.770799 0.683088 0.463617 0.045 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'
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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 178.4(4) . . ?
C1 C2 C3 112.6(3) . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H3 109.1 . . ?
C3 C2 H3 109.1 . . ?
H2 C2 H3 107.8 . . ?
C2 C3 C4 114.7(3) . . ?
C2 C3 H4 108.6 . . ?
C4 C3 H4 108.6 . . ?
C2 C3 H5 108.6 . . ?
C4 C3 H5 108.6 . . ?
H4 C3 H5 107.6 . . ?
C5 C4 C3 115.0(3) . . ?
C5 C4 H6 108.5 . . ?
C3 C4 H6 108.5 . . ?
C5 C4 H7 108.5 . . ?
C3 C4 H7 108.5 . . ?
H6 C4 H7 107.5 . . ?
O2 C5 C6 120.5(3) . . ?
O2 C5 C4 120.3(3) . . ?
C6 C5 C4 119.2(3) . . ?
C11 C6 C7 118.6(3) . . ?
C11 C6 C5 121.7(3) . . ?
C7 C6 C5 119.8(3) . . ?
O1 C7 C8 118.9(3) . . ?
O1 C7 C6 121.4(3) . . ?
C8 C7 C6 119.7(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H1 120.2 . . ?
C10 C9 H1 120.2 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 Br1 120.0(2) . . ?
C9 C10 Br1 119.3(2) . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H9 119.8 . . ?
C6 C11 H9 119.8 . . ?
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 C10 1.896(3) . ?
O1 C7 1.344(4) . ?
O2 C5 1.230(4) . ?
N1 C1 1.125(5) . ?
C1 C2 1.453(6) . ?
C2 C3 1.516(6) . ?
C2 H2 0.9700 . ?
C2 H3 0.9700 . ?
C3 C4 1.521(5) . ?
C3 H4 0.9700 . ?
C3 H5 0.9700 . ?
C4 C5 1.501(5) . ?
C4 H6 0.9700 . ?
C4 H7 0.9700 . ?
C5 C6 1.473(4) . ?
C6 C11 1.400(4) . ?
C6 C7 1.412(4) . ?
C7 C8 1.384(5) . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(5) . ?
C9 H1 0.9300 . ?
C10 C11 1.366(4) . ?
C11 H9 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
C1 C2 C3 C4 -59.1(5) . . . . ?
C2 C3 C4 C5 -69.6(4) . . . . ?
C3 C4 C5 O2 -1.4(5) . . . . ?
C3 C4 C5 C6 178.8(3) . . . . ?
O2 C5 C6 C11 -176.4(3) . . . . ?
C4 C5 C6 C11 3.4(4) . . . . ?
O2 C5 C6 C7 3.3(4) . . . . ?
C4 C5 C6 C7 -176.9(3) . . . . ?
C11 C6 C7 O1 178.8(3) . . . . ?
C5 C6 C7 O1 -0.9(4) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
O1 C7 C8 C9 -178.2(3) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C8 C9 C10 Br1 179.3(2) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
Br1 C10 C11 C6 -178.7(2) . . . . ?
C7 C6 C11 C10 -0.5(4) . . . . ?
C5 C6 C11 C10 179.2(3) . . . . ?
