#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:30:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178785 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/39/4103924.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_4103924
loop_
_publ_author_name
'Jason A. Bexrud'
'Patrick Eisenberger'
'David C. Leitch'
'Philippa R. Payne'
'Laurel L. Schafer'
_publ_section_title
;
 Selective C-H Activation α to Primary Amines. Bridging Metallaaziridines
 for Catalytic, Intramolecular α-Alkylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2116
_journal_page_last               2118
_journal_paper_doi               10.1021/ja808862w
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C27 H31 N O S'
_chemical_formula_sum            'C27 H31 N O S'
_chemical_formula_weight         417.59
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8333(6)
_cell_length_b                   9.9404(5)
_cell_length_c                   34.8473(15)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.661
_cell_measurement_theta_min      2.338
_cell_volume                     4445.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            59537
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.7
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0493
_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)+(0.0603P)²+3.3418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                3832
_reflns_number_total             5039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808862w_si_004.cif
_cod_data_source_block           ls139new
_cod_database_code               4103924
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
S001 S 0.75996(4) 0.16902(5) 0.100953(13) 0.02269(13) Uani 1 1 d .
O002 O 0.75651(11) 0.30107(14) 0.11772(4) 0.0316(3) Uani 1 1 d .
O200 O 0.66439(10) 0.09917(15) 0.09387(4) 0.0304(3) Uani 1 1 d .
N1 N 0.83367(12) 0.07426(16) 0.12746(4) 0.0224(3) Uani 1 1 d .
C005 C 0.87377(14) 0.1185(2) 0.16523(5) 0.0239(4) Uani 1 1 d .
H005 H 0.8562 0.2142 0.1674 0.029 Uiso 1 1 calc R
C006 C 1.03959(15) -0.0327(2) 0.16889(5) 0.0273(4) Uani 1 1 d .
C007 C 0.69849(16) 0.0570(2) 0.19450(6) 0.0357(5) Uani 1 1 d .
H00A H 0.6774 0.0166 0.1707 0.054 Uiso 1 1 calc R
H00B H 0.6776 0.1497 0.1948 0.054 Uiso 1 1 calc R
H00C H 0.6661 0.0104 0.2155 0.054 Uiso 1 1 calc R
C008 C 1.04582(15) 0.1912(2) 0.13571(6) 0.0272(4) Uani 1 1 d .
C009 C 0.99508(14) 0.1101(2) 0.16860(5) 0.0262(4) Uani 1 1 d .
C010 C 0.87517(19) 0.2969(2) 0.04634(6) 0.0372(5) Uani 1 1 d .
H010 H 0.8772 0.3701 0.0629 0.045 Uiso 1 1 calc R
C011 C 0.82455(15) 0.1811(2) 0.05657(5) 0.0270(4) Uani 1 1 d .
C012 C 1.11139(17) 0.1325(2) 0.10891(6) 0.0332(5) Uani 1 1 d .
H012 H 1.1226 0.0401 0.1098 0.040 Uiso 1 1 calc R
C013 C 1.02956(19) 0.3288(2) 0.13242(7) 0.0427(6) Uani 1 1 d .
H013 H 0.9848 0.3715 0.1495 0.051 Uiso 1 1 calc R
C014 C 0.98809(15) -0.1452(2) 0.15539(6) 0.0280(4) Uani 1 1 d .
H014 H 0.9193 -0.1366 0.1473 0.034 Uiso 1 1 calc R
C015 C 0.9234(2) 0.3029(3) 0.01071(7) 0.0474(6) Uani 1 1 d .
H015 H 0.9569 0.3819 0.0035 0.057 Uiso 1 1 calc R
C016 C 0.8232(2) 0.0718(3) 0.03220(7) 0.0472(6) Uani 1 1 d .
H016 H 0.7888 -0.0067 0.0392 0.057 Uiso 1 1 calc R
C017 C 0.85052(17) 0.1102(3) 0.23651(6) 0.0445(6) Uani 1 1 d .
H01A H 0.8247 0.2018 0.2379 0.053 Uiso 1 1 calc R
H01B H 0.8196 0.0599 0.2575 0.053 Uiso 1 1 calc R
C018 C 1.03531(17) -0.2700(2) 0.15341(6) 0.0340(5) Uani 1 1 d .
H018 H 0.9977 -0.3439 0.1447 0.041 Uiso 1 1 calc R
C019 C 1.0786(2) 0.4037(3) 0.10424(8) 0.0521(7) Uani 1 1 d .
H019 H 1.0664 0.4958 0.1027 0.063 Uiso 1 1 calc R
C020 C 0.81646(15) 0.0479(2) 0.19846(5) 0.0280(4) Uani 1 1 d .
H020 H 0.8363 -0.0473 0.1985 0.034 Uiso 1 1 calc R
C021 C 0.9232(2) 0.1962(3) -0.01402(7) 0.0457(6) Uani 1 1 d .
C022 C 1.16061(19) 0.2082(2) 0.08086(7) 0.0415(6) Uani 1 1 d .
H022 H 1.2048 0.1663 0.0634 0.050 Uiso 1 1 calc R
C023 C 0.96824(18) 0.1112(3) 0.24134(6) 0.0507(7) Uani 1 1 d .
H02A H 0.9863 0.1581 0.2648 0.061 Uiso 1 1 calc R
H02B H 0.9935 0.0195 0.2433 0.061 Uiso 1 1 calc R
C024 C 1.01991(17) 0.1802(3) 0.20749(6) 0.0411(6) Uani 1 1 d .
H02C H 1.0947 0.1807 0.2114 0.049 Uiso 1 1 calc R
H02D H 0.9966 0.2729 0.2063 0.049 Uiso 1 1 calc R
C025 C 1.14264(17) -0.0525(3) 0.18092(7) 0.0418(6) Uani 1 1 d .
H025 H 1.1797 0.0196 0.1911 0.050 Uiso 1 1 calc R
C026 C 1.13773(18) -0.2855(3) 0.16426(7) 0.0441(6) Uani 1 1 d .
H026 H 1.1703 -0.3688 0.1622 0.053 Uiso 1 1 calc R
C027 C 1.1448(2) 0.3438(3) 0.07858(7) 0.0453(6) Uani 1 1 d .
H027 H 1.1784 0.3947 0.0599 0.054 Uiso 1 1 calc R
C028 C 1.19069(18) -0.1767(3) 0.17807(8) 0.0519(7) Uani 1 1 d .
H028 H 1.2598 -0.1861 0.1856 0.062 Uiso 1 1 calc R
C029 C 0.8734(2) 0.0799(3) -0.00269(7) 0.0549(7) Uani 1 1 d .
H029 H 0.8737 0.0056 -0.0189 0.066 Uiso 1 1 calc R
C030 C 0.9747(3) 0.2042(4) -0.05284(8) 0.0733(10) Uani 1 1 d .
H03A H 0.9661 0.1201 -0.0660 0.110 Uiso 1 1 calc R
H03B H 1.0476 0.2227 -0.0497 0.110 Uiso 1 1 calc R
H03C H 0.9431 0.2749 -0.0676 0.110 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O200 S001 O002 119.13(9)
O200 S001 N1 108.43(8)
O002 S001 N1 108.45(8)
O200 S001 C011 106.59(9)
O002 S001 C011 108.02(9)
N1 S001 C011 105.39(9)
C005 N1 S001 122.41(13)
N1 C005 C020 111.52(15)
N1 C005 C009 113.39(15)
C020 C005 C009 113.24(16)
C014 C006 C025 116.1(2)
C014 C006 C009 124.75(17)
C025 C006 C009 119.0(2)
C012 C008 C013 116.8(2)
C012 C008 C009 122.43(19)
C013 C008 C009 120.77(19)
C006 C009 C008 109.37(16)
C006 C009 C024 109.45(17)
C008 C009 C024 109.04(17)
C006 C009 C005 114.94(16)
C008 C009 C005 109.64(16)
C024 C009 C005 104.20(16)
C011 C010 C015 118.7(2)
C010 C011 C016 120.5(2)
C010 C011 S001 120.68(16)
C016 C011 S001 118.80(16)
C008 C012 C022 121.6(2)
C019 C013 C008 121.4(2)
C006 C014 C018 122.25(19)
C021 C015 C010 121.9(2)
C029 C016 C011 119.4(2)
C023 C017 C020 112.52(18)
C026 C018 C014 120.4(2)
C027 C019 C013 120.8(2)
C007 C020 C017 109.82(17)
C007 C020 C005 112.30(17)
C017 C020 C005 109.34(17)
C015 C021 C029 118.1(2)
C015 C021 C030 121.6(2)
C029 C021 C030 120.3(3)
C027 C022 C012 120.6(2)
C024 C023 C017 110.6(2)
C023 C024 C009 112.66(19)
C028 C025 C006 121.6(2)
C028 C026 C018 118.9(2)
C022 C027 C019 118.9(2)
C026 C028 C025 120.7(2)
C016 C029 C021 121.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S001 O200 1.4308(14)
S001 O002 1.4375(14)
S001 N1 1.6232(16)
S001 C011 1.759(2)
N1 C005 1.480(2)
C005 C020 1.541(3)
C005 C009 1.563(3)
C006 C014 1.381(3)
C006 C025 1.401(3)
C006 C009 1.531(3)
C007 C020 1.523(3)
C008 C012 1.386(3)
C008 C013 1.388(3)
C008 C009 1.545(3)
C009 C024 1.556(3)
C010 C011 1.369(3)
C010 C015 1.389(3)
C011 C016 1.379(3)
C012 C022 1.386(3)
C013 C019 1.384(3)
C014 C018 1.383(3)
C015 C021 1.367(3)
C016 C029 1.378(3)
C017 C023 1.520(3)
C017 C020 1.527(3)
C018 C026 1.376(3)
C019 C027 1.370(4)
C021 C029 1.379(4)
C021 C030 1.508(3)
C022 C027 1.365(3)
C023 C024 1.517(3)
C025 C028 1.384(4)
C026 C028 1.365(4)
