#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:35:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180269 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/55/7115592.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_7115592
loop_
_publ_author_name
'Wenchao Ye'
'Laijun Zhang'
'Chuanfa Ni'
'Jian Rong'
'Jinbo Hu'
_publ_section_title
;
 Stereoselective [3+2] cycloaddition of N-tert-butanesulfinyl imines to
 arynes facilitated by a removable PhSO2CF2 group: synthesis and
 transformation of cyclic sulfoximines
;
_journal_name_full               Chem.Commun.
_journal_page_first              10596
_journal_paper_doi               10.1039/C4cc05042H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C21 H16 Br N O3 S'
_chemical_formula_sum            'C21 H16 Br N O3 S'
_chemical_formula_weight         442.32
_chemical_name_systematic
; 
 ? 
;
_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                 92.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.876(2)
_cell_length_b                   11.292(2)
_cell_length_c                   16.818(3)
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.94
_cell_measurement_theta_min      4.72
_cell_volume                     1873.3(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12287
_diffrn_reflns_theta_full        67.33
_diffrn_reflns_theta_max         67.33
_diffrn_reflns_theta_min         4.72
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_T_max  0.7859
_exptl_absorpt_correction_T_min  0.2472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00028(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0398
_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)+(0.0423P)²+1.9087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                2980
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05042h2.cif
_cod_data_source_block           040
_cod_original_cell_volume        1873.4(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7115592
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
Br1 Br 0.28725(4) 0.22821(3) 0.09520(3) 0.0868(2) Uani 1 1 d .
S1 S 0.66955(6) -0.57872(6) 0.05531(4) 0.04652(19) Uani 1 1 d .
O1 O 0.6505(3) -0.7016(2) 0.04312(18) 0.0848(8) Uani 1 1 d .
O2 O 0.6539(2) -0.5063(2) -0.01537(11) 0.0683(7) Uani 1 1 d .
O3 O 0.38331(18) -0.35740(17) 0.18533(13) 0.0528(5) Uani 1 1 d .
N1 N 0.5797(2) -0.5300(2) 0.12679(12) 0.0406(5) Uani 1 1 d .
H1B H 0.4975 -0.5523 0.1326 0.049 Uiso 1 1 calc R
C1 C 0.8229(2) -0.5409(2) 0.10456(15) 0.0420(6) Uani 1 1 d .
C2 C 0.8000(2) -0.4656(2) 0.16677(14) 0.0380(5) Uani 1 1 d .
C3 C 0.9102(3) -0.4160(3) 0.20871(16) 0.0455(6) Uani 1 1 d .
H3A H 0.8975 -0.3662 0.2518 0.055 Uiso 1 1 calc R
C4 C 1.0395(3) -0.4418(3) 0.18536(18) 0.0548(7) Uani 1 1 d .
H4A H 1.1139 -0.4066 0.2119 0.066 Uiso 1 1 calc R
C5 C 1.0598(3) -0.5186(3) 0.12346(19) 0.0598(8) Uani 1 1 d .
H5A H 1.1476 -0.5356 0.1094 0.072 Uiso 1 1 calc R
C6 C 0.9518(3) -0.5707(3) 0.08207(17) 0.0546(7) Uani 1 1 d .
H6A H 0.9648 -0.6237 0.0408 0.065 Uiso 1 1 calc R
C7 C 0.6499(2) -0.4444(2) 0.18119(14) 0.0368(5) Uani 1 1 d .
C8 C 0.6128(2) -0.3172(2) 0.15686(16) 0.0418(6) Uani 1 1 d .
H8A H 0.6682 -0.2632 0.1893 0.050 Uiso 1 1 calc R
H8B H 0.6354 -0.3056 0.1019 0.050 Uiso 1 1 calc R
C9 C 0.4645(2) -0.2846(2) 0.16480(15) 0.0403(6) Uani 1 1 d .
C10 C 0.4236(2) -0.1600(2) 0.14606(14) 0.0391(5) Uani 1 1 d .
C11 C 0.5115(3) -0.0788(2) 0.11393(16) 0.0452(6) Uani 1 1 d .
H11A H 0.5991 -0.1021 0.1032 0.054 Uiso 1 1 calc R
C12 C 0.4707(3) 0.0361(3) 0.09770(17) 0.0503(7) Uani 1 1 d .
H12A H 0.5296 0.0899 0.0757 0.060 Uiso 1 1 calc R
C13 C 0.3411(3) 0.0691(2) 0.11473(18) 0.0506(7) Uani 1 1 d .
C14 C 0.2514(3) -0.0089(3) 0.14657(19) 0.0554(7) Uani 1 1 d .
H14A H 0.1643 0.0153 0.1576 0.066 Uiso 1 1 calc R
C15 C 0.2929(3) -0.1235(3) 0.16175(17) 0.0492(6) Uani 1 1 d .
H15A H 0.2328 -0.1772 0.1828 0.059 Uiso 1 1 calc R
C16 C 0.6253(2) -0.4753(2) 0.26796(14) 0.0373(5) Uani 1 1 d .
C17 C 0.6475(3) -0.3928(3) 0.32824(17) 0.0517(7) Uani 1 1 d .
H17A H 0.6673 -0.3147 0.3154 0.062 Uiso 1 1 calc R
C18 C 0.6406(3) -0.4255(3) 0.40753(17) 0.0601(8) Uani 1 1 d .
H18A H 0.6561 -0.3694 0.4474 0.072 Uiso 1 1 calc R
C19 C 0.6114(3) -0.5395(3) 0.42727(17) 0.0557(8) Uani 1 1 d .
H19A H 0.6081 -0.5613 0.4805 0.067 Uiso 1 1 calc R
C20 C 0.5868(3) -0.6216(3) 0.36851(17) 0.0521(7) Uani 1 1 d .
H20A H 0.5652 -0.6990 0.3819 0.062 Uiso 1 1 calc R
C21 C 0.5939(3) -0.5901(2) 0.28905(15) 0.0438(6) Uani 1 1 d .
H21A H 0.5774 -0.6468 0.2496 0.053 Uiso 1 1 calc R
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'
S S 0.3331 0.5567 '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
O1 S1 O2 115.33(17)
O1 S1 N1 111.47(14)
O2 S1 N1 112.14(13)
O1 S1 C1 114.57(15)
O2 S1 C1 107.92(13)
N1 S1 C1 93.35(11)
C7 N1 S1 114.98(15)
C7 N1 H1B 122.5
S1 N1 H1B 122.5
C2 C1 C6 123.0(3)
C2 C1 S1 110.00(18)
C6 C1 S1 126.7(2)
C1 C2 C3 118.9(2)
C1 C2 C7 114.4(2)
C3 C2 C7 126.7(2)
C4 C3 C2 118.8(3)
C4 C3 H3A 120.6
C2 C3 H3A 120.6
C5 C4 C3 121.1(3)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C6 C5 C4 120.9(3)
C6 C5 H5A 119.5
C4 C5 H5A 119.5
C5 C6 C1 117.2(3)
C5 C6 H6A 121.4
C1 C6 H6A 121.4
N1 C7 C16 110.4(2)
N1 C7 C2 103.16(19)
C16 C7 C2 108.32(19)
N1 C7 C8 110.4(2)
C16 C7 C8 114.9(2)
C2 C7 C8 108.94(19)
C9 C8 C7 114.9(2)
C9 C8 H8A 108.5
C7 C8 H8A 108.5
C9 C8 H8B 108.5
C7 C8 H8B 108.5
H8A C8 H8B 107.5
O3 C9 C10 121.6(2)
O3 C9 C8 120.9(2)
C10 C9 C8 117.5(2)
C11 C10 C15 118.7(2)
C11 C10 C9 122.4(2)
C15 C10 C9 118.9(2)
C12 C11 C10 121.0(2)
C12 C11 H11A 119.5
C10 C11 H11A 119.5
C13 C12 C11 118.6(3)
C13 C12 H12A 120.7
C11 C12 H12A 120.7
C14 C13 C12 122.0(3)
C14 C13 Br1 119.6(2)
C12 C13 Br1 118.4(2)
C13 C14 C15 118.8(3)
C13 C14 H14A 120.6
C15 C14 H14A 120.6
C14 C15 C10 120.9(3)
C14 C15 H15A 119.6
C10 C15 H15A 119.6
C21 C16 C17 118.2(2)
C21 C16 C7 120.4(2)
C17 C16 C7 121.1(2)
C16 C17 C18 120.6(3)
C16 C17 H17A 119.7
C18 C17 H17A 119.7
C19 C18 C17 120.4(3)
C19 C18 H18A 119.8
C17 C18 H18A 119.8
C18 C19 C20 119.7(3)
C18 C19 H19A 120.1
C20 C19 H19A 120.1
C19 C20 C21 120.5(3)
C19 C20 H20A 119.8
C21 C20 H20A 119.8
C16 C21 C20 120.6(3)
C16 C21 H21A 119.7
C20 C21 H21A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.898(3)
S1 O1 1.414(3)
S1 O2 1.445(2)
S1 N1 1.624(2)
S1 C1 1.743(3)
O3 C9 1.211(3)
N1 C7 1.480(3)
N1 H1B 0.8600
C1 C2 1.375(4)
C1 C6 1.388(4)
C2 C3 1.387(4)
C2 C7 1.533(3)
C3 C4 1.385(4)
C3 H3A 0.9300
C4 C5 1.377(5)
C4 H4A 0.9300
C5 C6 1.377(5)
C5 H5A 0.9300
C6 H6A 0.9300
C7 C16 1.531(3)
C7 C8 1.533(4)
C8 C9 1.522(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.493(4)
C10 C11 1.390(4)
C10 C15 1.393(3)
C11 C12 1.381(4)
C11 H11A 0.9300
C12 C13 1.377(4)
C12 H12A 0.9300
C13 C14 1.376(4)
C14 C15 1.377(4)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C21 1.383(4)
C16 C17 1.387(4)
C17 C18 1.389(4)
C17 H17A 0.9300
C18 C19 1.364(5)
C18 H18A 0.9300
C19 C20 1.368(4)
C19 H19A 0.9300
C20 C21 1.388(4)
C20 H20A 0.9300
C21 H21A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.86 2.50 2.930(3) 111.4 3_645
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
O1 S1 N1 C7 138.4(2)
O2 S1 N1 C7 -90.5(2)
C1 S1 N1 C7 20.35(19)
O1 S1 C1 C2 -130.0(2)
O2 S1 C1 C2 100.1(2)
N1 S1 C1 C2 -14.5(2)
O1 S1 C1 C6 55.8(3)
O2 S1 C1 C6 -74.2(3)
N1 S1 C1 C6 171.3(3)
C6 C1 C2 C3 0.7(4)
S1 C1 C2 C3 -173.8(2)
C6 C1 C2 C7 179.8(2)
S1 C1 C2 C7 5.3(3)
C1 C2 C3 C4 1.5(4)
C7 C2 C3 C4 -177.5(2)
C2 C3 C4 C5 -2.3(4)
C3 C4 C5 C6 1.0(5)
C4 C5 C6 C1 1.1(5)
C2 C1 C6 C5 -1.9(4)
S1 C1 C6 C5 171.6(2)
S1 N1 C7 C16 -134.76(17)
S1 N1 C7 C2 -19.2(2)
S1 N1 C7 C8 97.1(2)
C1 C2 C7 N1 7.8(3)
C3 C2 C7 N1 -173.2(2)
C1 C2 C7 C16 124.8(2)
C3 C2 C7 C16 -56.1(3)
C1 C2 C7 C8 -109.5(2)
C3 C2 C7 C8 69.5(3)
N1 C7 C8 C9 65.1(3)
C16 C7 C8 C9 -60.6(3)
C2 C7 C8 C9 177.7(2)
C7 C8 C9 O3 -3.3(4)
C7 C8 C9 C10 176.9(2)
O3 C9 C10 C11 -172.6(3)
C8 C9 C10 C11 7.2(4)
O3 C9 C10 C15 7.8(4)
C8 C9 C10 C15 -172.4(2)
C15 C10 C11 C12 0.0(4)
C9 C10 C11 C12 -179.6(2)
C10 C11 C12 C13 0.6(4)
C11 C12 C13 C14 -0.6(4)
C11 C12 C13 Br1 178.2(2)
C12 C13 C14 C15 0.0(5)
Br1 C13 C14 C15 -178.8(2)
C13 C14 C15 C10 0.7(4)
C11 C10 C15 C14 -0.6(4)
C9 C10 C15 C14 179.0(3)
N1 C7 C16 C21 24.7(3)
C2 C7 C16 C21 -87.6(3)
C8 C7 C16 C21 150.3(2)
N1 C7 C16 C17 -162.1(2)
C2 C7 C16 C17 85.6(3)
C8 C7 C16 C17 -36.4(3)
C21 C16 C17 C18 1.1(4)
C7 C16 C17 C18 -172.3(2)
C16 C17 C18 C19 -0.2(5)
C17 C18 C19 C20 -0.9(5)
C18 C19 C20 C21 1.2(4)
C17 C16 C21 C20 -0.8(4)
C7 C16 C21 C20 172.6(2)
C19 C20 C21 C16 -0.3(4)
