#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:37:16 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178956 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/85/4118510.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_4118510
loop_
_publ_author_name
'Anike Nörder'
'Sarah A. Warren'
'Eberhardt Herdtweck'
'Stefan M. Huber'
'Thorsten Bach'
_publ_contact_author_address
;
       Department Chemie,
       Lehrstuhl für Anorganische Chemie,
       Technische Universität München,
       Lichtenbergstrasse 4,
       D-85747 Garching bei München,
       Germany.
;
_publ_contact_author_email       eberhardt.herdtweck@ch.tum.de
_publ_contact_author_fax         '+49(0)89 289 13473'
_publ_contact_author_name
;
       Dr. Eberhardt Herdtweck
;
_publ_contact_author_phone       '+49(0)89 289 13143'
_publ_section_title
;
 Diastereotopos-Differentiation in the Rh-Catalyzed Amination of Benzylic
 Methylene Groups in the α-Position to a Stereogenic Center
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13524
_journal_page_last               13531
_journal_paper_doi               10.1021/ja3066682
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C12 H15 Br Cl3 N O4 S'
_chemical_formula_sum            'C12 H15 Br Cl3 N O4 S'
_chemical_formula_weight         455.57
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             12-Jan-12
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record
;
   12-Jan-12  Updated by the Author E.H.
              Text writing by E.H.
              Checkcif    OK
   22-Feb-12  Updated by the Author E.H.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.4214(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1241(4)
_cell_length_b                   9.1560(3)
_cell_length_c                   17.8862(6)
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      1.97
_cell_volume                     1772.00(11)
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      123(1)
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38646
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       column
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+2.4528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                3126
_reflns_number_total             3245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja3066682_si_002.cif
_cod_data_source_block           Compound_syn-4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4118510
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br Uani 0.56014(2) 0.29648(3) -0.03160(1) 1.000 0.0302(1) . .
Cl1 Cl Uani 0.47695(6) 0.37697(6) 0.37996(4) 1.000 0.0321(2) . .
Cl2 Cl Uani 0.67201(7) 0.21124(8) 0.47921(4) 1.000 0.0430(2) . .
Cl3 Cl Uani 0.44095(6) 0.07069(7) 0.40674(3) 1.000 0.0304(2) . .
S1 S Uani 0.78710(4) 0.22491(5) 0.27180(3) 1.000 0.0139(1) . .
O1 O Uani 0.17046(15) 0.12615(19) 0.18404(11) 1.000 0.0316(5) . .
O2 O Uani 0.67753(13) 0.27333(15) 0.30995(8) 1.000 0.0180(4) . .
O3 O Uani 0.84306(13) 0.36195(16) 0.26197(9) 1.000 0.0195(4) . .
O4 O Uani 0.85645(13) 0.11221(16) 0.31745(8) 1.000 0.0192(4) . .
N1 N Uani 0.72760(16) 0.1553(2) 0.18943(10) 1.000 0.0153(5) . .
C1 C Uani 0.64235(19) 0.2408(2) 0.12799(11) 1.000 0.0164(6) . .
C2 C Uani 0.50959(19) 0.2179(2) 0.13354(12) 1.000 0.0167(6) . .
C3 C Uani 0.44551(19) 0.3294(2) 0.16030(12) 1.000 0.0190(6) . .
C4 C Uani 0.3313(2) 0.3043(2) 0.17700(13) 1.000 0.0209(6) . .
C5 C Uani 0.2797(2) 0.1655(3) 0.16639(13) 1.000 0.0215(6) . .
C6 C Uani 0.3398(2) 0.0545(2) 0.13614(13) 1.000 0.0222(6) . .
C7 C Uani 0.4540(2) 0.0804(2) 0.12023(12) 1.000 0.0193(6) . .
C8 C Uani 0.1188(3) 0.2233(3) 0.23023(19) 1.000 0.0394(9) . .
C9 C Uani 0.6727(2) 0.1933(2) 0.05221(12) 1.000 0.0208(6) . .
C10 C Uani 0.8075(2) 0.2287(3) 0.04810(13) 1.000 0.0271(7) . .
C11 C Uani 0.5512(2) 0.2054(2) 0.39594(13) 1.000 0.0217(7) . .
C12 C Uani 0.59799(19) 0.1588(2) 0.32631(12) 1.000 0.0186(6) . .
H1 H Uiso 0.709(2) 0.076(3) 0.1929(14) 1.000 0.017(7) . .
H9 H Uiso 0.65850 0.08580 0.04540 1.000 0.0250 calc R
H11 H Uiso 0.66280 0.34690 0.13620 1.000 0.0200 calc R
H31 H Uiso 0.48050 0.42450 0.16730 1.000 0.0230 calc R
H41 H Uiso 0.28900 0.38140 0.19550 1.000 0.0250 calc R
H61 H Uiso 0.30240 -0.03900 0.12640 1.000 0.0270 calc R
H71 H Uiso 0.49500 0.00400 0.10010 1.000 0.0230 calc R
H81 H Uiso 0.18140 0.24750 0.27690 1.000 0.0590 calc R
H82 H Uiso 0.04800 0.17660 0.24430 1.000 0.0590 calc R
H83 H Uiso 0.09160 0.31290 0.20120 1.000 0.0590 calc R
H101 H Uiso 0.82130 0.33430 0.05330 1.000 0.0410 calc R
H102 H Uiso 0.82120 0.19600 -0.00140 1.000 0.0410 calc R
H103 H Uiso 0.86510 0.17810 0.08980 1.000 0.0410 calc R
H121 H Uiso 0.64460 0.06600 0.33710 1.000 0.0220 calc R
H122 H Uiso 0.52760 0.14360 0.28160 1.000 0.0220 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_publ_flag
O2 S1 O3 101.94(8) yes
O2 S1 O4 108.80(8) yes
O2 S1 N1 108.14(9) yes
O3 S1 O4 120.82(9) yes
O3 S1 N1 109.58(10) yes
O4 S1 N1 106.98(9) yes
C5 O1 C8 117.9(2) yes
S1 O2 C12 116.77(12) yes
S1 N1 C1 121.61(14) yes
S1 N1 H1 111.5(18) no
C1 N1 H1 114.9(18) no
N1 C1 C2 109.90(16) yes
C2 C1 C9 115.84(17) no
N1 C1 C9 105.60(16) yes
C1 C2 C7 120.79(18) no
C1 C2 C3 120.33(17) no
C3 C2 C7 118.5(2) no
C2 C3 C4 121.27(18) no
C3 C4 C5 119.42(19) no
C4 C5 C6 120.0(2) no
O1 C5 C6 115.4(2) yes
O1 C5 C4 124.6(2) yes
C5 C6 C7 120.04(19) no
C2 C7 C6 120.63(19) no
C1 C9 C10 113.31(17) no
Br1 C9 C1 107.87(14) yes
Br1 C9 C10 108.42(14) yes
Cl1 C11 C12 110.71(14) yes
Cl2 C11 Cl3 109.81(12) yes
Cl2 C11 C12 111.28(16) yes
Cl3 C11 C12 105.67(13) yes
Cl1 C11 Cl2 110.26(11) yes
Cl1 C11 Cl3 108.99(12) yes
O2 C12 C11 107.75(15) yes
N1 C1 H11 108.00 no
C2 C1 H11 108.00 no
C9 C1 H11 108.00 no
C2 C3 H31 119.00 no
C4 C3 H31 119.00 no
C3 C4 H41 120.00 no
C5 C4 H41 120.00 no
C5 C6 H61 120.00 no
C7 C6 H61 120.00 no
C2 C7 H71 120.00 no
C6 C7 H71 120.00 no
O1 C8 H81 109.00 no
O1 C8 H82 109.00 no
O1 C8 H83 109.00 no
H81 C8 H82 110.00 no
H81 C8 H83 109.00 no
H82 C8 H83 109.00 no
Br1 C9 H9 109.00 no
C1 C9 H9 109.00 no
C10 C9 H9 109.00 no
C9 C10 H101 109.00 no
C9 C10 H102 109.00 no
C9 C10 H103 109.00 no
H101 C10 H102 109.00 no
H101 C10 H103 110.00 no
H102 C10 H103 109.00 no
O2 C12 H121 110.00 no
O2 C12 H122 110.00 no
C11 C12 H121 110.00 no
C11 C12 H122 110.00 no
H121 C12 H122 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 1.959(2) yes
Cl1 C11 1.767(2) yes
Cl2 C11 1.760(2) yes
Cl3 C11 1.781(2) yes
S1 O2 1.5918(15) yes
S1 O3 1.4296(15) yes
S1 O4 1.4263(15) yes
S1 N1 1.6007(18) yes
O1 C5 1.373(3) yes
O1 C8 1.423(4) yes
O2 C12 1.445(2) yes
N1 C1 1.495(3) yes
N1 H1 0.76(3) no
C1 C9 1.534(3) no
C1 C2 1.518(3) no
C2 C3 1.392(3) no
C2 C7 1.399(3) no
C3 C4 1.390(3) no
C4 C5 1.389(3) no
C5 C6 1.393(3) no
C6 C7 1.385(3) no
C9 C10 1.553(3) no
C11 C12 1.518(3) no
C1 H11 1.0000 no
C3 H31 0.9500 no
C4 H41 0.9500 no
C6 H61 0.9500 no
C7 H71 0.9500 no
C8 H81 0.9800 no
C8 H82 0.9800 no
C8 H83 0.9800 no
C9 H9 1.0000 no
C10 H101 0.9800 no
C10 H102 0.9800 no
C10 H103 0.9800 no
C12 H121 0.9900 no
C12 H122 0.9900 no
