#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:36:12 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284281 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246540.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_7246540
loop_
_publ_author_name
'Zhang, Zhongyi'
'Hou, Zhong-Wei'
'Chen, Hao'
'Li, Pinhua'
'Wang, Lei'
_publ_section_title
;
 Electrochemical electrophilic bromination/spirocyclization of
 N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3543
_journal_page_last               3548
_journal_paper_doi               10.1039/D3GC00728F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C15 H20 Br N O2'
_chemical_formula_weight         326.23
_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-2014/7
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                93.881(5)
_cell_angle_beta                 97.142(5)
_cell_angle_gamma                100.629(4)
_cell_formula_units_Z            2
_cell_length_a                   7.079(2)
_cell_length_b                   9.363(3)
_cell_length_c                   11.864(3)
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.22
_cell_volume                     763.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3901
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.691
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0443
_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)+(0.0663P)²+0.3324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2034
_reflns_number_total             2672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00728f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7246540--7246541.cif.'
_cod_database_code               7246540
_shelx_shelxl_version_number     2014/7
_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   0.541
_shelx_estimated_absorpt_t_max   0.565
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 0.17186(6) 0.58524(4) 0.41155(4) 0.0644(2) Uani 1 1 d . . . . .
O2 O 0.5477(4) 1.0367(3) 0.3552(3) 0.0619(8) Uani 1 1 d . . . . .
N1 N 0.7379(4) 0.9158(3) 0.2557(2) 0.0370(6) Uani 1 1 d . . . . .
C4 C 0.5460(5) 0.6772(3) 0.2470(3) 0.0362(8) Uani 1 1 d . . . . .
C8 C 0.5166(5) 0.7737(3) 0.3540(3) 0.0345(7) Uani 1 1 d . . . . .
C7 C 0.7424(5) 0.7641(3) 0.2210(3) 0.0395(8) Uani 1 1 d . . . . .
H7A H 0.8507 0.7332 0.2644 0.047 Uiso 1 1 calc R U . . .
H7B H 0.7530 0.7509 0.1404 0.047 Uiso 1 1 calc R U . . .
O1 O 0.1973(6) 0.3172(4) 0.0540(3) 0.0976(13) Uani 1 1 d . . . . .
C11 C 0.5997(5) 0.9257(4) 0.3227(3) 0.0408(8) Uani 1 1 d . . . . .
C3 C 0.5589(5) 0.5243(4) 0.2666(3) 0.0450(9) Uani 1 1 d . . . . .
H3 H 0.6494 0.5082 0.3258 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3953(5) 0.6859(4) 0.1492(3) 0.0475(9) Uani 1 1 d . . . . .
H5 H 0.3786 0.7780 0.1305 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8553(5) 1.0397(4) 0.2092(3) 0.0402(8) Uani 1 1 d . . . . .
C9 C 0.3079(5) 0.7711(4) 0.3734(4) 0.0497(9) Uani 1 1 d . . . . .
H9A H 0.2372 0.7970 0.3048 0.060 Uiso 1 1 calc R U . . .
H9B H 0.3072 0.8451 0.4345 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6393(6) 0.7485(4) 0.4639(3) 0.0496(9) Uani 1 1 d . . . . .
H10A H 0.5888 0.6542 0.4869 0.074 Uiso 1 1 calc R U . . .
H10B H 0.6350 0.8226 0.5230 0.074 Uiso 1 1 calc R U . . .
H10C H 0.7712 0.7528 0.4506 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4473(6) 0.4088(4) 0.2039(4) 0.0574(11) Uani 1 1 d . . . . .
H2 H 0.4637 0.3157 0.2203 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2844(6) 0.5717(5) 0.0877(3) 0.0635(12) Uani 1 1 d . . . . .
H6 H 0.1932 0.5863 0.0283 0.076 Uiso 1 1 calc R U . . .
C1 C 0.3008(7) 0.4239(5) 0.1105(4) 0.0649(13) Uani 1 1 d . . . . .
C14 C 0.7319(7) 1.0831(5) 0.1088(4) 0.0721(13) Uani 1 1 d . . . . .
H14A H 0.6885 1.0008 0.0529 0.108 Uiso 1 1 calc R U . . .
H14B H 0.8073 1.1612 0.0757 0.108 Uiso 1 1 calc R U . . .
H14C H 0.6216 1.1148 0.1342 0.108 Uiso 1 1 calc R U . . .
C15 C 1.0301(6) 0.9934(5) 0.1670(5) 0.0773(15) Uani 1 1 d . . . . .
H15A H 1.1094 0.9639 0.2295 0.116 Uiso 1 1 calc R U . . .
H15B H 1.1043 1.0737 0.1356 0.116 Uiso 1 1 calc R U . . .
H15C H 0.9875 0.9131 0.1092 0.116 Uiso 1 1 calc R U . . .
C13 C 0.9226(9) 1.1690(6) 0.2991(5) 0.104(2) Uani 1 1 d . . . . .
H13A H 0.8116 1.2014 0.3231 0.156 Uiso 1 1 calc R U . . .
H13B H 1.0007 1.2471 0.2675 0.156 Uiso 1 1 calc R U . . .
H13C H 0.9978 1.1400 0.3636 0.156 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
C11 N1 C7 111.5(3) . . ?
C11 N1 C12 125.5(3) . . ?
C7 N1 C12 122.5(3) . . ?
C3 C4 C5 112.2(3) . . ?
C3 C4 C7 111.3(3) . . ?
C5 C4 C7 107.5(3) . . ?
C3 C4 C8 115.1(3) . . ?
C5 C4 C8 109.9(3) . . ?
C7 C4 C8 100.1(2) . . ?
C9 C8 C11 107.8(3) . . ?
C9 C8 C10 110.6(3) . . ?
C11 C8 C10 107.4(3) . . ?
C9 C8 C4 116.2(3) . . ?
C11 C8 C4 100.7(3) . . ?
C10 C8 C4 113.2(3) . . ?
N1 C7 C4 104.3(3) . . ?
N1 C7 H7A 110.9 . . ?
C4 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C4 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O2 C11 N1 126.7(3) . . ?
O2 C11 C8 124.2(3) . . ?
N1 C11 C8 109.0(3) . . ?
C2 C3 C4 123.4(4) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C6 C5 C4 124.4(4) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N1 C12 C14 108.2(3) . . ?
N1 C12 C15 109.9(3) . . ?
C14 C12 C15 108.2(3) . . ?
N1 C12 C13 111.0(3) . . ?
C14 C12 C13 109.9(4) . . ?
C15 C12 C13 109.5(4) . . ?
C8 C9 Br1 114.7(2) . . ?
C8 C9 H9A 108.6 . . ?
Br1 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
Br1 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O1 C1 C6 121.9(5) . . ?
O1 C1 C2 121.6(5) . . ?
C6 C1 C2 116.5(3) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.938(4) . ?
O2 C11 1.219(4) . ?
N1 C11 1.347(4) . ?
N1 C7 1.459(4) . ?
N1 C12 1.478(4) . ?
C4 C3 1.483(5) . ?
C4 C5 1.492(5) . ?
C4 C7 1.553(5) . ?
C4 C8 1.566(5) . ?
C8 C9 1.519(5) . ?
C8 C11 1.525(5) . ?
C8 C10 1.532(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1 C1 1.225(5) . ?
C3 C2 1.334(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.317(5) . ?
C5 H5 0.9300 . ?
C12 C14 1.511(5) . ?
C12 C15 1.514(6) . ?
C12 C13 1.522(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C1 1.453(6) . ?
C2 H2 0.9300 . ?
C6 C1 1.451(6) . ?
C6 H6 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
C3 C4 C8 C9 -88.4(4) . . . . ?
C5 C4 C8 C9 39.4(4) . . . . ?
C7 C4 C8 C9 152.2(3) . . . . ?
C3 C4 C8 C11 155.5(3) . . . . ?
C5 C4 C8 C11 -76.7(3) . . . . ?
C7 C4 C8 C11 36.1(3) . . . . ?
C3 C4 C8 C10 41.1(4) . . . . ?
C5 C4 C8 C10 168.9(3) . . . . ?
C7 C4 C8 C10 -78.2(3) . . . . ?
C11 N1 C7 C4 16.0(4) . . . . ?
C12 N1 C7 C4 -156.7(3) . . . . ?
C3 C4 C7 N1 -154.6(3) . . . . ?
C5 C4 C7 N1 82.2(3) . . . . ?
C8 C4 C7 N1 -32.5(3) . . . . ?
C7 N1 C11 O2 -171.9(4) . . . . ?
C12 N1 C11 O2 0.6(6) . . . . ?
C7 N1 C11 C8 8.7(4) . . . . ?
C12 N1 C11 C8 -178.8(3) . . . . ?
C9 C8 C11 O2 29.2(5) . . . . ?
C10 C8 C11 O2 -89.9(4) . . . . ?
C4 C8 C11 O2 151.4(4) . . . . ?
C9 C8 C11 N1 -151.4(3) . . . . ?
C10 C8 C11 N1 89.5(3) . . . . ?
C4 C8 C11 N1 -29.2(3) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C7 C4 C3 C2 -120.7(4) . . . . ?
C8 C4 C3 C2 126.4(4) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C7 C4 C5 C6 123.3(4) . . . . ?
C8 C4 C5 C6 -128.7(4) . . . . ?
C11 N1 C12 C14 -77.9(4) . . . . ?
C7 N1 C12 C14 93.8(4) . . . . ?
C11 N1 C12 C15 164.1(4) . . . . ?
C7 N1 C12 C15 -24.2(5) . . . . ?
C11 N1 C12 C13 42.8(5) . . . . ?
C7 N1 C12 C13 -145.5(4) . . . . ?
C11 C8 C9 Br1 178.8(2) . . . . ?
C10 C8 C9 Br1 -64.1(4) . . . . ?
C4 C8 C9 Br1 66.8(4) . . . . ?
C4 C3 C2 C1 -0.6(6) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C5 C6 C1 O1 179.6(4) . . . . ?
C5 C6 C1 C2 -0.6(6) . . . . ?
C3 C2 C1 O1 -179.2(4) . . . . ?
C3 C2 C1 C6 1.0(6) . . . . ?
