#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:46:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178963 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/92/4119227.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_4119227
loop_
_publ_author_name
'Feng Chen'
'Chong Kiat Tan'
'Ying-Yeung Yeung'
_publ_section_title
;
 C2-Symmetric Cyclic Selenium-Catalyzed Enantioselective
 Bromoaminocyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1232
_journal_page_last               1235
_journal_paper_doi               10.1021/ja311202e
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C23 H21 Br N2 O4 S'
_chemical_formula_weight         501.39
_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                 94.078(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6702(13)
_cell_length_b                   11.5801(19)
_cell_length_c                   23.557(4)
_cell_measurement_reflns_used    850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.47
_cell_volume                     2087.1(6)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14371
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0362
_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)+(0.0481P)²+0.4580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                3977
_reflns_number_total             4760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311202e_si_003.cif
_cod_data_source_block           c823
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4119227
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 0.01150(3) 0.20661(2) 0.792797(10) 0.01614(9) Uani 1 1 d .
S1 S -0.15802(7) 0.51478(5) 0.82741(3) 0.01341(14) Uani 1 1 d .
O1 O -0.1742(2) 0.44194(14) 0.87577(7) 0.0169(4) Uani 1 1 d .
O2 O -0.2978(2) 0.52171(15) 0.78357(8) 0.0188(4) Uani 1 1 d .
O3 O 0.0108(3) 0.71707(15) 1.02138(8) 0.0224(4) Uani 1 1 d .
O4 O 0.0808(3) 0.89362(16) 1.00351(8) 0.0246(4) Uani 1 1 d .
N1 N 0.0137(3) 0.47541(18) 0.79632(8) 0.0143(4) Uani 1 1 d .
N2 N 0.0213(3) 0.79838(18) 0.98895(9) 0.0173(4) Uani 1 1 d .
C1 C 0.1792(3) 0.4240(2) 0.82463(10) 0.0132(5) Uani 1 1 d .
C2 C 0.2929(3) 0.4110(2) 0.77225(10) 0.0160(5) Uani 1 1 d .
H2A H 0.3972 0.4614 0.7770 0.019 Uiso 1 1 calc R
H2B H 0.3325 0.3301 0.7689 0.019 Uiso 1 1 calc R
C3 C 0.1800(3) 0.4459(2) 0.71908(11) 0.0205(5) Uani 1 1 d .
H3A H 0.2510 0.4849 0.6913 0.025 Uiso 1 1 calc R
H3B H 0.1223 0.3777 0.7007 0.025 Uiso 1 1 calc R
C4 C 0.0470(3) 0.5276(2) 0.74091(11) 0.0196(5) Uani 1 1 d .
H4A H 0.0948 0.6067 0.7457 0.023 Uiso 1 1 calc R
H4B H -0.0607 0.5301 0.7151 0.023 Uiso 1 1 calc R
C5 C 0.2592(3) 0.5073(2) 0.87060(10) 0.0127(5) Uani 1 1 d .
C6 C 0.3374(3) 0.6100(2) 0.85414(11) 0.0173(5) Uani 1 1 d .
H6 H 0.3435 0.6265 0.8148 0.021 Uiso 1 1 calc R
C7 C 0.4063(4) 0.6882(2) 0.89461(12) 0.0219(6) Uani 1 1 d .
H7 H 0.4589 0.7575 0.8826 0.026 Uiso 1 1 calc R
C8 C 0.3989(3) 0.6661(2) 0.95217(12) 0.0211(6) Uani 1 1 d .
H8 H 0.4472 0.7191 0.9797 0.025 Uiso 1 1 calc R
C9 C 0.3197(3) 0.5649(2) 0.96890(11) 0.0184(5) Uani 1 1 d .
H9 H 0.3126 0.5493 1.0083 0.022 Uiso 1 1 calc R
C10 C 0.2509(3) 0.4865(2) 0.92879(10) 0.0155(5) Uani 1 1 d .
H10 H 0.1974 0.4177 0.9411 0.019 Uiso 1 1 calc R
C11 C 0.1396(3) 0.30625(19) 0.85076(10) 0.0134(5) Uani 1 1 d .
H11 H 0.0591 0.3205 0.8816 0.016 Uiso 1 1 calc R
C12 C 0.2918(3) 0.2362(2) 0.87659(10) 0.0151(5) Uani 1 1 d .
C13 C 0.2511(3) 0.1368(2) 0.90627(11) 0.0171(5) Uani 1 1 d .
H13 H 0.1320 0.1187 0.9106 0.021 Uiso 1 1 calc R
C14 C 0.3799(3) 0.0637(2) 0.92963(11) 0.0201(5) Uani 1 1 d .
H14 H 0.3490 -0.0042 0.9492 0.024 Uiso 1 1 calc R
C15 C 0.5544(3) 0.0902(2) 0.92425(11) 0.0202(5) Uani 1 1 d .
H15 H 0.6434 0.0398 0.9396 0.024 Uiso 1 1 calc R
C16 C 0.5982(3) 0.1902(2) 0.89649(11) 0.0202(6) Uani 1 1 d .
H16 H 0.7177 0.2091 0.8935 0.024 Uiso 1 1 calc R
C17 C 0.4687(3) 0.2634(2) 0.87293(11) 0.0173(5) Uani 1 1 d .
H17 H 0.5004 0.3321 0.8542 0.021 Uiso 1 1 calc R
C18 C -0.1226(3) 0.6571(2) 0.85319(11) 0.0137(5) Uani 1 1 d .
C19 C -0.1408(3) 0.7509(2) 0.81601(11) 0.0170(5) Uani 1 1 d .
H19 H -0.1750 0.7391 0.7769 0.020 Uiso 1 1 calc R
C20 C -0.1083(3) 0.8620(2) 0.83689(12) 0.0195(5) Uani 1 1 d .
H20 H -0.1221 0.9266 0.8121 0.023 Uiso 1 1 calc R
C21 C -0.0562(3) 0.8783(2) 0.89350(11) 0.0183(5) Uani 1 1 d .
H21 H -0.0318 0.9536 0.9080 0.022 Uiso 1 1 calc R
C22 C -0.0400(3) 0.7829(2) 0.92886(11) 0.0150(5) Uani 1 1 d .
C23 C -0.0744(3) 0.6718(2) 0.91031(11) 0.0147(5) Uani 1 1 d .
H23 H -0.0654 0.6081 0.9357 0.018 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 0.0033 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 S1 O2 120.21(11)
O1 S1 N1 108.30(10)
O2 S1 N1 106.26(11)
O1 S1 C18 107.21(11)
O2 S1 C18 106.44(11)
N1 S1 C18 107.92(11)
C4 N1 C1 110.98(19)
C4 N1 S1 118.84(16)
C1 N1 S1 126.57(16)
O3 N2 O4 123.8(2)
O3 N2 C22 118.6(2)
O4 N2 C22 117.6(2)
N1 C1 C11 110.01(18)
N1 C1 C5 110.02(18)
C11 C1 C5 110.70(19)
N1 C1 C2 100.78(18)
C11 C1 C2 111.57(19)
C5 C1 C2 113.34(19)
C3 C2 C1 107.8(2)
C4 C3 C2 104.2(2)
N1 C4 C3 102.01(19)
C10 C5 C6 117.9(2)
C10 C5 C1 122.5(2)
C6 C5 C1 119.5(2)
C7 C6 C5 120.9(2)
C8 C7 C6 120.7(2)
C7 C8 C9 118.9(2)
C10 C9 C8 120.8(2)
C9 C10 C5 120.9(2)
C12 C11 C1 117.9(2)
C12 C11 Br1 107.10(15)
C1 C11 Br1 109.97(16)
C13 C12 C17 117.9(2)
C13 C12 C11 116.8(2)
C17 C12 C11 125.3(2)
C14 C13 C12 121.7(2)
C13 C14 C15 119.6(2)
C16 C15 C14 119.8(2)
C15 C16 C17 120.6(2)
C16 C17 C12 120.4(2)
C23 C18 C19 121.6(2)
C23 C18 S1 118.21(18)
C19 C18 S1 120.19(19)
C20 C19 C18 119.3(2)
C21 C20 C19 120.0(2)
C20 C21 C22 118.8(2)
C23 C22 C21 123.2(2)
C23 C22 N2 117.4(2)
C21 C22 N2 119.4(2)
C22 C23 C18 117.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.992(2)
S1 O1 1.4299(18)
S1 O2 1.4369(17)
S1 N1 1.617(2)
S1 C18 1.771(2)
O3 N2 1.219(3)
O4 N2 1.233(3)
N1 C4 1.477(3)
N1 C1 1.514(3)
N2 C22 1.471(3)
C1 C11 1.535(3)
C1 C5 1.544(3)
C1 C2 1.568(3)
C2 C3 1.526(3)
C3 C4 1.509(4)
C5 C10 1.398(3)
C5 C6 1.399(3)
C6 C7 1.392(3)
C7 C8 1.385(4)
C8 C9 1.389(4)
C9 C10 1.388(3)
C11 C12 1.513(3)
C12 C13 1.394(4)
C12 C17 1.402(3)
C13 C14 1.385(4)
C14 C15 1.387(4)
C15 C16 1.383(4)
C16 C17 1.390(4)
C18 C23 1.380(3)
C18 C19 1.396(3)
C19 C20 1.394(4)
C20 C21 1.378(4)
C21 C22 1.384(3)
C22 C23 1.378(3)
