#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024308.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_4024308
loop_
_publ_author_name
'Zhan-Guo Chen'
'Jun-Fa Wei'
'Run-Tao Li'
'Xian-Ying Shi'
'Peng-Fei Zhao'
_publ_section_title
;
Copper Powder-Catalyzed Regio- and Stereoselective Aminobromination of
α,β-Unsaturated Ketones with TsNH2 and NBS as Nitrogen and Halogen Sources
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1371
_journal_page_last               1373
_journal_paper_doi               10.1021/jo8023768
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H19 Br N O3 S'
_chemical_formula_sum            'C22 H19 Br N O3 S'
_chemical_formula_weight         457.35
_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                 99.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6611(19)
_cell_length_b                   18.333(4)
_cell_length_c                   12.119(2)
_cell_measurement_reflns_used    4161
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.22
_cell_volume                     2117.8(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17834
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  0.8524
_exptl_absorpt_correction_T_min  0.7900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0631
_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)+(0.1290P)²+2.6719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2778
_reflns_number_total             4161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8023768_si_001.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024308
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.13370(7) 0.20534(4) 1.08704(6) 0.0753(3) Uani 1 1 d . . .
C1 C -0.1580(6) 0.1864(3) 1.0004(4) 0.0519(13) Uani 1 1 d . . .
C2 C -0.2634(6) 0.1593(4) 1.0521(5) 0.0645(15) Uani 1 1 d . . .
H2 H -0.2506 0.1151 1.0900 0.077 Uiso 1 1 calc R . .
C3 C -0.3883(7) 0.1966(5) 1.0486(7) 0.087(2) Uani 1 1 d . . .
H3 H -0.4581 0.1780 1.0852 0.104 Uiso 1 1 calc R . .
C4 C -0.4092(8) 0.2608(6) 0.9914(8) 0.098(3) Uani 1 1 d . . .
H4 H -0.4933 0.2859 0.9892 0.118 Uiso 1 1 calc R . .
C5 C -0.3063(10) 0.2888(4) 0.9369(7) 0.097(3) Uani 1 1 d . . .
H5 H -0.3217 0.3325 0.8979 0.117 Uiso 1 1 calc R . .
C6 C -0.1788(7) 0.2520(4) 0.9397(5) 0.0740(18) Uani 1 1 d . . .
H6 H -0.1096 0.2705 0.9023 0.089 Uiso 1 1 calc R . .
C7 C -0.0223(5) 0.1459(3) 1.0086(4) 0.0465(11) Uani 1 1 d . . .
H7 H -0.0297 0.1024 1.0542 0.076 Uiso 1 1 calc R . .
C8 C 0.0201(5) 0.1203(3) 0.8985(4) 0.0423(10) Uani 1 1 d . . .
H8 H 0.0274 0.1623 0.8497 0.071 Uiso 1 1 calc R . .
C9 C 0.1600(5) 0.0798(3) 0.9211(4) 0.0413(10) Uani 1 1 d . . .
C10 C 0.2799(5) 0.1009(3) 0.8673(4) 0.0413(10) Uani 1 1 d . . .
C11 C 0.2823(5) 0.1638(3) 0.8047(4) 0.0519(12) Uani 1 1 d . . .
H11 H 0.2074 0.1962 0.7985 0.062 Uiso 1 1 calc R . .
C12 C 0.3952(6) 0.1790(3) 0.7511(5) 0.0600(14) Uani 1 1 d . . .
H12 H 0.3958 0.2214 0.7091 0.072 Uiso 1 1 calc R . .
C13 C 0.5069(6) 0.1311(3) 0.7603(5) 0.0641(15) Uani 1 1 d . . .
H13 H 0.5825 0.1410 0.7239 0.077 Uiso 1 1 calc R . .
C14 C 0.5060(6) 0.0683(3) 0.8234(5) 0.0627(15) Uani 1 1 d . . .
H14 H 0.5813 0.0361 0.8302 0.075 Uiso 1 1 calc R . .
C15 C 0.3940(5) 0.0539(3) 0.8759(4) 0.0502(12) Uani 1 1 d . . .
H15 H 0.3942 0.0117 0.9183 0.060 Uiso 1 1 calc R . .
C16 C 0.0211(5) 0.0146(3) 0.6700(4) 0.0421(11) Uani 1 1 d . . .
C17 C 0.0420(7) -0.0580(3) 0.6954(5) 0.0620(15) Uani 1 1 d . . .
H17 H -0.0206 -0.0835 0.7318 0.074 Uiso 1 1 calc R . .
C18 C 0.1595(8) -0.0929(4) 0.6655(6) 0.079(2) Uani 1 1 d . . .
H18 H 0.1743 -0.1420 0.6824 0.094 Uiso 1 1 calc R . .
C19 C 0.2535(7) -0.0564(4) 0.6117(5) 0.0736(19) Uani 1 1 d . . .
C20 C 0.2279(6) 0.0149(4) 0.5868(5) 0.0691(18) Uani 1 1 d . . .
H20 H 0.2899 0.0402 0.5497 0.083 Uiso 1 1 calc R . .
C21 C 0.1140(5) 0.0512(3) 0.6144(4) 0.0507(12) Uani 1 1 d . . .
H21 H 0.0994 0.1001 0.5957 0.061 Uiso 1 1 calc R . .
C22 C 0.3833(11) -0.0961(7) 0.5871(8) 0.140(4) Uani 1 1 d . . .
H22A H 0.4319 -0.0658 0.5413 0.210 Uiso 1 1 calc R . .
H22B H 0.3559 -0.1408 0.5484 0.210 Uiso 1 1 calc R . .
H22C H 0.4441 -0.1067 0.6561 0.210 Uiso 1 1 calc R . .
N1 N -0.0901(4) 0.0706(2) 0.8452(3) 0.0470(10) Uani 1 1 d . . .
O1 O 0.1662(4) 0.0272(2) 0.9836(3) 0.0604(10) Uani 1 1 d . . .
O3 O -0.2394(4) 0.0131(3) 0.6902(4) 0.0863(15) Uani 1 1 d . . .
O4 O -0.1278(5) 0.1314(2) 0.6614(3) 0.0756(13) Uani 1 1 d . . .
S2 S -0.12201(13) 0.06046(9) 0.71003(11) 0.0541(4) 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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.7(5) . . ?
C2 C1 C7 119.8(5) . . ?
C6 C1 C7 120.5(5) . . ?
C1 C2 C3 121.1(7) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.9(8) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.7(8) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.3(7) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C1 C7 C8 116.8(4) . . ?
C1 C7 Br 110.5(3) . . ?
C8 C7 Br 107.3(3) . . ?
C1 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
Br C7 H7 107.3 . . ?
N1 C8 C9 109.5(4) . . ?
N1 C8 C7 107.3(4) . . ?
C9 C8 C7 110.3(4) . . ?
N1 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
C7 C8 H8 109.9 . . ?
O1 C9 C10 121.3(4) . . ?
O1 C9 C8 116.6(4) . . ?
C10 C9 C8 122.0(4) . . ?
C11 C10 C15 118.3(4) . . ?
C11 C10 C9 123.2(4) . . ?
C15 C10 C9 118.4(4) . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 121.6(5) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C17 C16 C21 119.8(5) . . ?
C17 C16 S2 119.8(4) . . ?
C21 C16 S2 120.4(4) . . ?
C16 C17 C18 118.7(6) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C18 117.7(6) . . ?
C20 C19 C22 123.0(8) . . ?
C18 C19 C22 119.3(8) . . ?
C19 C20 C21 122.5(6) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C20 C21 C16 119.5(5) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 S2 121.3(3) . . ?
O3 S2 O4 120.8(3) . . ?
O3 S2 N1 104.8(2) . . ?
O4 S2 N1 107.5(2) . . ?
O3 S2 C16 107.7(3) . . ?
O4 S2 C16 107.6(2) . . ?
N1 S2 C16 107.7(2) . . ?
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
Br C7 1.974(5) . ?
C1 C2 1.372(8) . ?
C1 C6 1.407(9) . ?
C1 C7 1.496(7) . ?
C2 C3 1.381(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.531(6) . ?
C7 H7 0.9800 . ?
C8 N1 1.469(6) . ?
C8 C9 1.528(6) . ?
C8 H8 0.9800 . ?
C9 O1 1.222(6) . ?
C9 C10 1.471(6) . ?
C10 C11 1.382(7) . ?
C10 C15 1.390(7) . ?
C11 C12 1.385(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.373(8) . ?
C16 C21 1.381(7) . ?
C16 S2 1.753(5) . ?
C17 C18 1.402(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(10) . ?
C19 C22 1.521(9) . ?
C20 C21 1.373(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S2 1.627(4) . ?
O3 S2 1.418(5) . ?
O4 S2 1.425(5) . ?
