#------------------------------------------------------------------------------
#$Date: 2020-08-07 02:25:47 +0300 (Fri, 07 Aug 2020) $
#$Revision: 255140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038652.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_4038652
loop_
_publ_author_name
'Ubale, Akash'
'Chaudhari, Moreshwar Bhagwan'
'Shaikh, Moseen A.'
'Gnanaprakasam, Boopathy'
_publ_section_title
;
 Manganese-Catalyzed Synthesis of Quaternary Peroxides: Application in
 Catalytic Deperoxidation and Rearrangement Reactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00837
_journal_year                    2020
_chemical_formula_sum            'C23 H28 Br N O5'
_chemical_formula_weight         478.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.152(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6710(6)
_cell_length_b                   22.8755(15)
_cell_length_c                   9.5065(6)
_cell_measurement_reflns_used    22991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.325
_cell_measurement_theta_min      3.865
_cell_volume                     2318.9(2)
_computing_cell_refinement       'SHELXTL Suite'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker microfocus'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1144
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22991
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.325
_diffrn_reflns_theta_min         3.865
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,2008
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.370
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0819
_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)+(0.0956P)²+9.8504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3286
_reflns_number_total             4738
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00837_si_002.cif
_cod_data_source_block           compound9e
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038652
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 0.24402(7) 0.67486(3) 1.05582(8) 0.0446(3) Uani 1 1 d . . . . .
C1 C 0.6561(5) 0.6524(2) 0.6216(5) 0.0169(10) Uani 1 1 d . . . . .
H1 H 0.6413 0.6828 0.5473 0.020 Uiso 1 1 calc R U . . .
C2 C 0.5566(5) 0.6577(2) 0.7310(5) 0.0185(11) Uani 1 1 d . . . . .
C3 C 0.5194(5) 0.6099(2) 0.8069(5) 0.0202(11) Uani 1 1 d . . . . .
H3 H 0.5575 0.5730 0.7920 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4274(5) 0.6149(2) 0.9043(5) 0.0205(11) Uani 1 1 d . . . . .
H4 H 0.4004 0.5817 0.9547 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3753(5) 0.6691(3) 0.9274(5) 0.0254(12) Uani 1 1 d . . . . .
C6 C 0.4118(5) 0.7180(2) 0.8552(6) 0.0263(12) Uani 1 1 d . . . . .
H6 H 0.3762 0.7552 0.8737 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5021(5) 0.7118(3) 0.7548(6) 0.0238(12) Uani 1 1 d . . . . .
H7 H 0.5268 0.7448 0.7019 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0801(5) 0.6410(3) 0.5240(6) 0.0266(12) Uani 1 1 d . . . . .
C9 C 1.0722(6) 0.6758(4) 0.3881(7) 0.0443(18) Uani 1 1 d . . . . .
H9A H 0.9887 0.6710 0.3431 0.066 Uiso 1 1 calc R U . . .
H9B H 1.1357 0.6615 0.3245 0.066 Uiso 1 1 calc R U . . .
H9C H 1.0872 0.7172 0.4087 0.066 Uiso 1 1 calc R U . . .
C10 C 1.2050(5) 0.6486(3) 0.5995(7) 0.0379(15) Uani 1 1 d . . . . .
H10A H 1.2171 0.6899 0.6240 0.057 Uiso 1 1 calc R U . . .
H10B H 1.2717 0.6360 0.5383 0.057 Uiso 1 1 calc R U . . .
H10C H 1.2077 0.6251 0.6856 0.057 Uiso 1 1 calc R U . . .
C11 C 1.0485(7) 0.5772(3) 0.5009(10) 0.058(2) Uani 1 1 d . . . . .
H11A H 1.0505 0.5569 0.5917 0.086 Uiso 1 1 calc R U . . .
H11B H 1.1099 0.5596 0.4397 0.086 Uiso 1 1 calc R U . . .
H11C H 0.9645 0.5739 0.4564 0.086 Uiso 1 1 calc R U . . .
C12 C 0.5486(5) 0.5733(2) 0.3443(5) 0.0200(11) Uani 1 1 d . . . . .
C13 C 0.4177(5) 0.5540(3) 0.2984(6) 0.0239(12) Uani 1 1 d . . . . .
H13A H 0.3924 0.5210 0.3564 0.036 Uiso 1 1 calc R U . . .
H13B H 0.4168 0.5421 0.1993 0.036 Uiso 1 1 calc R U . . .
H13C H 0.3591 0.5866 0.3097 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6428(5) 0.5236(3) 0.3285(6) 0.0252(12) Uani 1 1 d . . . . .
H14A H 0.7256 0.5364 0.3646 0.038 Uiso 1 1 calc R U . . .
H14B H 0.6474 0.5132 0.2289 0.038 Uiso 1 1 calc R U . . .
H14C H 0.6158 0.4896 0.3820 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5896(6) 0.6283(3) 0.2684(6) 0.0315(14) Uani 1 1 d . . . . .
H15A H 0.5286 0.6595 0.2827 0.047 Uiso 1 1 calc R U . . .
H15B H 0.5945 0.6201 0.1675 0.047 Uiso 1 1 calc R U . . .
H15C H 0.6722 0.6405 0.3062 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7913(5) 0.6583(2) 0.6843(5) 0.0193(11) Uani 1 1 d . . . . .
C17 C 0.8232(4) 0.6135(2) 0.7972(5) 0.0208(11) Uani 1 1 d . . . . .
C18 C 0.8300(5) 0.5535(2) 0.7922(6) 0.0249(12) Uani 1 1 d . . . . .
H18 H 0.8200 0.5334 0.7050 0.030 Uiso 1 1 calc R U . . .
C19 C 0.8518(5) 0.5229(3) 0.9167(7) 0.0322(14) Uani 1 1 d . . . . .
H19 H 0.8572 0.4814 0.9145 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8658(5) 0.5517(3) 1.0431(6) 0.0313(14) Uani 1 1 d . . . . .
H20 H 0.8796 0.5298 1.1272 0.038 Uiso 1 1 calc R U . . .
C21 C 0.8600(5) 0.6126(3) 1.0501(6) 0.0290(13) Uani 1 1 d . . . . .
H21 H 0.8709 0.6326 1.1372 0.035 Uiso 1 1 calc R U . . .
C22 C 0.8376(5) 0.6427(2) 0.9250(6) 0.0214(11) Uani 1 1 d . . . . .
C23 C 0.8047(5) 0.7169(2) 0.7666(6) 0.0218(11) Uani 1 1 d . . . . .
N1 N 0.8255(4) 0.7033(2) 0.9045(5) 0.0240(10) Uani 1 1 d . . . . .
H1A H 0.8307 0.7293 0.9728 0.029 Uiso 1 1 calc R U . . .
O1 O 0.6573(3) 0.59575(16) 0.5575(4) 0.0199(8) Uani 1 1 d . . . . .
O2 O 0.5319(3) 0.58601(16) 0.4916(4) 0.0192(8) Uani 1 1 d . . . . .
O3 O 0.8667(3) 0.65908(17) 0.5648(4) 0.0222(8) Uani 1 1 d . . . . .
O4 O 0.9965(3) 0.66694(18) 0.6233(4) 0.0261(9) Uani 1 1 d . . . . .
O5 O 0.7950(4) 0.76498(17) 0.7122(4) 0.0261(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 C2 112.4(4) . . ?
O1 C1 C16 102.7(4) . . ?
C2 C1 C16 113.3(4) . . ?
O1 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C16 C1 H1 109.4 . . ?
C3 C2 C7 119.4(5) . . ?
C3 C2 C1 121.2(5) . . ?
C7 C2 C1 119.4(5) . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 Br1 119.7(4) . . ?
C4 C5 Br1 118.4(4) . . ?
C5 C6 C7 118.4(5) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O4 C8 C10 101.4(5) . . ?
O4 C8 C11 110.5(5) . . ?
C10 C8 C11 111.8(6) . . ?
O4 C8 C9 108.9(5) . . ?
C10 C8 C9 111.5(5) . . ?
C11 C8 C9 112.2(6) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 101.0(4) . . ?
O2 C12 C15 109.9(4) . . ?
C13 C12 C15 112.5(5) . . ?
O2 C12 C14 110.5(4) . . ?
C13 C12 C14 111.1(4) . . ?
C15 C12 C14 111.5(4) . . ?
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 . . ?
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 . . ?
O3 C16 C17 117.2(4) . . ?
O3 C16 C1 104.0(4) . . ?
C17 C16 C1 113.3(4) . . ?
O3 C16 C23 110.3(4) . . ?
C17 C16 C23 102.3(4) . . ?
C1 C16 C23 109.6(4) . . ?
C18 C17 C22 120.4(5) . . ?
C18 C17 C16 131.5(5) . . ?
C22 C17 C16 108.0(5) . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.9(6) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 121.1(6) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 117.5(5) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C17 121.4(5) . . ?
C21 C22 N1 128.3(5) . . ?
C17 C22 N1 110.3(5) . . ?
O5 C23 N1 128.7(5) . . ?
O5 C23 C16 124.0(5) . . ?
N1 C23 C16 107.2(5) . . ?
C23 N1 C22 111.7(4) . . ?
C23 N1 H1A 124.1 . . ?
C22 N1 H1A 124.1 . . ?
C1 O1 O2 107.2(3) . . ?
C12 O2 O1 107.4(3) . . ?
C16 O3 O4 104.6(3) . . ?
C8 O4 O3 107.1(4) . . ?
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 C5 1.897(5) . ?
C1 O1 1.432(6) . ?
C1 C2 1.518(7) . ?
C1 C16 1.546(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.377(7) . ?
C2 C7 1.390(8) . ?
C3 C4 1.380(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(8) . ?
C6 C7 1.389(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O4 1.450(6) . ?
C8 C10 1.500(8) . ?
C8 C11 1.511(9) . ?
C8 C9 1.517(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O2 1.448(6) . ?
C12 C13 1.514(7) . ?
C12 C15 1.522(8) . ?
C12 C14 1.527(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O3 1.417(6) . ?
C16 C17 1.513(7) . ?
C16 C23 1.557(7) . ?
C17 C18 1.374(8) . ?
C17 C22 1.390(7) . ?
C18 C19 1.388(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(8) . ?
C21 H21 0.9500 . ?
C22 N1 1.407(7) . ?
C23 O5 1.217(7) . ?
C23 N1 1.358(7) . ?
N1 H1A 0.8800 . ?
O1 O2 1.473(5) . ?
O3 O4 1.484(5) . ?
