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#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/59/4025933.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_4025933
loop_
_publ_author_name
'Karl J. Bonney'
'D. Christopher Braddock'
'Andrew J. P. White'
'Muhammad Yaqoob'
_publ_section_title
;
 Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening: Capture of
 the Oxonium Ion with an Added External Nucleophile
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              97
_journal_page_last               104
_journal_paper_doi               10.1021/jo101617h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C15 H16 Br N O5'
_chemical_formula_sum            'C15 H16 Br N O5'
_chemical_formula_weight         370.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.081(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6954(4)
_cell_length_b                   6.38506(18)
_cell_length_c                   17.6341(6)
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.1463
_cell_measurement_theta_min      3.3230
_cell_volume                     1495.70(8)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4007
_diffrn_reflns_theta_full        62.00
_diffrn_reflns_theta_max         64.20
_diffrn_reflns_theta_min         3.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.972
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) 
(compiled Jan  8 2009,16:24:04) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       'platy needles'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.071
_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     199
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0507P)²+3.0478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                1949
_reflns_number_total             2399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101617h_si_001_1.cif
_cod_data_source_block           6b
_cod_database_code               4025933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.4863(2) -0.0575(5) 0.10316(18) 0.0485(8) Uani 1 1 d .
C1 C 0.5813(4) 0.0581(8) 0.1206(3) 0.0531(12) Uani 1 1 d .
H1A H 0.6310 -0.0139 0.0963 0.064 Uiso 1 1 calc R
C2 C 0.5546(3) 0.2695(7) 0.0831(3) 0.0462(11) Uani 1 1 d .
H2A H 0.5254 0.2480 0.0259 0.055 Uiso 1 1 calc R
Br Br 0.68310(4) 0.42999(9) 0.09664(3) 0.0596(2) Uani 1 1 d .
C3 C 0.4814(4) 0.4008(7) 0.1152(3) 0.0478(11) Uani 1 1 d .
H3A H 0.5123 0.4334 0.1708 0.057 Uiso 1 1 calc R
H3B H 0.4699 0.5350 0.0863 0.057 Uiso 1 1 calc R
C4 C 0.3810(3) 0.2952(7) 0.1095(3) 0.0479(11) Uani 1 1 d .
H4A H 0.3308 0.4044 0.1124 0.057 Uiso 1 1 calc R
H4B H 0.3596 0.2281 0.0575 0.057 Uiso 1 1 calc R
C5 C 0.3791(3) 0.1344(8) 0.1702(3) 0.0475(11) Uani 1 1 d .
H5A H 0.3089 0.0789 0.1604 0.057 Uiso 1 1 calc R
C6 C 0.4496(4) -0.0513(7) 0.1737(3) 0.0497(11) Uani 1 1 d .
H6A H 0.4099 -0.1820 0.1755 0.060 Uiso 1 1 calc R
C7 C 0.5455(4) -0.0630(8) 0.2397(3) 0.0524(12) Uani 1 1 d .
H7A H 0.5345 -0.0018 0.2885 0.063 Uiso 1 1 calc R
H7B H 0.5683 -0.2097 0.2498 0.063 Uiso 1 1 calc R
C8 C 0.6207(4) 0.0629(9) 0.2098(3) 0.0601(13) Uani 1 1 d .
H8A H 0.6885 -0.0009 0.2258 0.072 Uiso 1 1 calc R
H8B H 0.6242 0.2084 0.2297 0.072 Uiso 1 1 calc R
O9 O 0.4006(2) 0.2498(5) 0.24512(18) 0.0491(8) Uani 1 1 d .
C10 C 0.3547(3) 0.1799(7) 0.2995(2) 0.0372(9) Uani 1 1 d .
O10 O 0.3079(2) 0.0197(5) 0.29408(17) 0.0470(7) Uani 1 1 d .
C11 C 0.3645(3) 0.3312(6) 0.3651(2) 0.0324(9) Uani 1 1 d .
C12 C 0.4054(3) 0.5310(6) 0.3640(2) 0.0369(9) Uani 1 1 d .
H12A H 0.4294 0.5742 0.3203 0.044 Uiso 1 1 calc R
C13 C 0.4110(3) 0.6666(6) 0.4261(2) 0.0377(9) Uani 1 1 d .
H13A H 0.4392 0.8025 0.4259 0.045 Uiso 1 1 calc R
C14 C 0.3748(3) 0.5994(6) 0.4883(2) 0.0370(9) Uani 1 1 d .
C15 C 0.3340(3) 0.4025(7) 0.4915(2) 0.0413(10) Uani 1 1 d .
H15A H 0.3103 0.3600 0.5355 0.050 Uiso 1 1 calc R
C16 C 0.3289(3) 0.2697(7) 0.4290(2) 0.0376(9) Uani 1 1 d .
H16A H 0.3006 0.1341 0.4296 0.045 Uiso 1 1 calc R
N17 N 0.3814(3) 0.7396(6) 0.5558(2) 0.0443(9) Uani 1 1 d .
O18 O 0.4190(3) 0.9133(5) 0.5538(2) 0.0574(9) Uani 1 1 d .
O19 O 0.3495(3) 0.6778(6) 0.6107(2) 0.0661(10) 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'
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'
Br Br -0.6763 1.2805 '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
C6 O1 C1 106.4(3)
O1 C1 C2 104.5(4)
O1 C1 C8 107.4(4)
C2 C1 C8 114.8(4)
C1 C2 C3 116.3(4)
C1 C2 Br 107.1(3)
C3 C2 Br 108.3(3)
C4 C3 C2 113.6(4)
C5 C4 C3 115.7(4)
O9 C5 C4 105.3(4)
O9 C5 C6 111.5(4)
C4 C5 C6 116.5(4)
O1 C6 C5 109.6(4)
O1 C6 C7 103.8(4)
C5 C6 C7 119.2(4)
C8 C7 C6 104.1(4)
C7 C8 C1 104.4(4)
C10 O9 C5 116.5(3)
O10 C10 O9 124.1(4)
O10 C10 C11 124.2(4)
O9 C10 C11 111.7(3)
C16 C11 C12 119.4(4)
C16 C11 C10 117.6(4)
C12 C11 C10 122.9(4)
C13 C12 C11 120.4(4)
C14 C13 C12 118.3(4)
C13 C14 C15 122.9(4)
C13 C14 N17 119.4(4)
C15 C14 N17 117.7(4)
C16 C15 C14 117.9(4)
C15 C16 C11 121.0(4)
O19 N17 O18 123.3(4)
O19 N17 C14 118.7(4)
O18 N17 C14 118.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.452(5)
O1 C1 1.462(6)
C1 C2 1.508(7)
C1 C8 1.534(7)
C2 C3 1.518(6)
C2 Br 2.001(5)
C3 C4 1.512(6)
C4 C5 1.488(6)
C5 O9 1.479(5)
C5 C6 1.520(7)
C6 C7 1.530(7)
C7 C8 1.500(7)
O9 C10 1.345(5)
C10 O10 1.199(5)
C10 C11 1.488(6)
C11 C16 1.389(5)
C11 C12 1.394(6)
C12 C13 1.384(6)
C13 C14 1.377(6)
C14 C15 1.382(6)
C14 N17 1.475(5)
C15 C16 1.379(6)
N17 O19 1.220(5)
N17 O18 1.226(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091720
