#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028039.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_4028039
loop_
_publ_author_name
'Boris Egart'
'Dieter Lentz'
'Constantin Czekelius'
_publ_section_title
;
 Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2490
_journal_page_last               2499
_journal_paper_doi               10.1021/jo3026725
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H16 Br N O3 S'
_chemical_formula_weight         382.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.162(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.412(5)
_cell_length_b                   11.143(8)
_cell_length_c                   18.737(12)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.85
_cell_volume                     1543.4(18)
_computing_cell_refinement       'SAINT (BRUKER-AXS)'
_computing_data_collection       'SMART (BRUKER-AXS)'
_computing_data_reduction        'SAINT (BRUKER-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13797
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       platelett
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         13797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+1.9489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                11493
_reflns_number_total             13797
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo3026725_si_002.cif
_cod_data_source_block           be452_1a
_cod_original_cell_volume        1543.3(18)
_cod_database_code               4028039
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.51186(3) 0.005665(17) 0.308370(9) 0.02469(7) Uani 1 1 d .
C1 C 0.4831(3) 0.14357(16) 0.17801(10) 0.0233(4) Uani 1 1 d .
H1A H 0.5845 0.1856 0.2047 0.028 Uiso 1 1 calc R
H1B H 0.5044 0.1440 0.1265 0.028 Uiso 1 1 calc R
C2 C 0.4658(2) 0.01667(15) 0.20490(9) 0.0186(4) Uani 1 1 d .
H2 H 0.5496 -0.0377 0.1806 0.022 Uiso 1 1 calc R
C3 C 0.2696(2) -0.01308(14) 0.18100(9) 0.0161(4) Uani 1 1 d .
H3 H 0.2124 -0.0601 0.2188 0.019 Uiso 1 1 calc R
C4 C 0.2573(2) -0.08187(14) 0.11059(9) 0.0160(4) Uani 1 1 d .
C5 C 0.2948(3) -0.20413(15) 0.11274(10) 0.0219(4) Uani 1 1 d .
H5 H 0.3235 -0.2424 0.1574 0.026 Uiso 1 1 calc R
C6 C 0.2906(3) -0.27038(16) 0.05023(10) 0.0260(4) Uani 1 1 d .
H6 H 0.3157 -0.3540 0.0522 0.031 Uiso 1 1 calc R
C7 C 0.2500(3) -0.21572(16) -0.01508(10) 0.0239(4) Uani 1 1 d .
H7 H 0.2464 -0.2614 -0.0580 0.029 Uiso 1 1 calc R
C8 C 0.2150(3) -0.09451(17) -0.01749(10) 0.0269(4) Uani 1 1 d .
H8 H 0.1878 -0.0564 -0.0623 0.032 Uiso 1 1 calc R
C9 C 0.2189(3) -0.02733(15) 0.04495(10) 0.0228(4) Uani 1 1 d .
H9 H 0.1952 0.0564 0.0426 0.027 Uiso 1 1 calc R
C10 C 0.0688(2) 0.14045(14) 0.30891(9) 0.0159(4) Uani 1 1 d .
C11 C 0.0530(2) 0.03941(15) 0.35087(9) 0.0179(4) Uani 1 1 d .
H11 H -0.0006 -0.0318 0.3312 0.021 Uiso 1 1 calc R
C12 C 0.1168(3) 0.04430(15) 0.42204(10) 0.0199(4) Uani 1 1 d .
H12 H 0.1069 -0.0246 0.4513 0.024 Uiso 1 1 calc R
C13 C 0.1954(3) 0.14837(16) 0.45170(9) 0.0223(4) Uani 1 1 d .
C14 C 0.2089(3) 0.24863(15) 0.40753(10) 0.0220(4) Uani 1 1 d .
H14 H 0.2625 0.3201 0.4269 0.026 Uiso 1 1 calc R
C15 C 0.1466(2) 0.24610(14) 0.33689(10) 0.0189(4) Uani 1 1 d .
H15 H 0.1561 0.3150 0.3075 0.023 Uiso 1 1 calc R
C16 C 0.2614(3) 0.15349(18) 0.52951(10) 0.0324(5) Uani 1 1 d .
H16A H 0.1749 0.1988 0.5561 0.049 Uiso 1 1 calc R
H16B H 0.3797 0.1931 0.5344 0.049 Uiso 1 1 calc R
H16C H 0.2725 0.0718 0.5487 0.049 Uiso 1 1 calc R
N1 N 0.18037(19) 0.10743(11) 0.17125(7) 0.0165(3) Uani 1 1 d .
O1 O 0.31517(17) 0.19968(10) 0.18989(7) 0.0203(3) Uani 1 1 d .
O2 O -0.11356(17) 0.03405(10) 0.20271(7) 0.0188(3) Uani 1 1 d .
O3 O -0.05994(17) 0.25294(10) 0.19575(7) 0.0217(3) Uani 1 1 d .
S1 S 0.00003(6) 0.13612(3) 0.21771(2) 0.01494(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 0.0033 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'
S S 0.1246 0.1234 '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
O1 C1 C2 105.23(14)
C1 C2 C3 101.97(14)
C1 C2 Br1 112.22(12)
C3 C2 Br1 111.88(12)
N1 C3 C4 110.29(14)
N1 C3 C2 104.07(13)
C4 C3 C2 111.04(14)
C9 C4 C5 118.96(16)
C9 C4 C3 123.01(15)
C5 C4 C3 117.97(15)
C6 C5 C4 120.42(17)
C7 C6 C5 120.35(17)
C8 C7 C6 119.39(17)
C7 C8 C9 120.65(18)
C4 C9 C8 120.21(17)
C11 C10 C15 121.51(17)
C11 C10 S1 120.16(13)
C15 C10 S1 118.27(13)
C10 C11 C12 118.60(16)
C11 C12 C13 121.37(16)
C12 C13 C14 118.31(17)
C12 C13 C16 120.96(16)
C14 C13 C16 120.72(16)
C15 C14 C13 121.44(16)
C14 C15 C10 118.77(16)
O1 N1 C3 108.26(13)
O1 N1 S1 107.41(10)
C3 N1 S1 117.87(11)
C1 O1 N1 104.14(12)
O3 S1 O2 120.15(9)
O3 S1 N1 105.52(7)
O2 S1 N1 103.07(8)
O3 S1 C10 108.63(8)
O2 S1 C10 109.86(8)
N1 S1 C10 108.99(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.948(2)
C1 O1 1.425(2)
C1 C2 1.510(3)
C2 C3 1.527(3)
C3 N1 1.502(2)
C3 C4 1.523(2)
C4 C9 1.383(3)
C4 C5 1.390(3)
C5 C6 1.383(3)
C6 C7 1.380(3)
C7 C8 1.376(3)
C8 C9 1.387(3)
C10 C11 1.383(2)
C10 C15 1.396(2)
C10 S1 1.748(2)
C11 C12 1.383(3)
C12 C13 1.395(3)
C13 C14 1.398(3)
C13 C16 1.505(3)
C14 C15 1.370(3)
N1 O1 1.4581(19)
N1 S1 1.6779(17)
O2 S1 1.4308(14)
O3 S1 1.4264(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139092596
