#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/48/4114859.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_4114859
loop_
_publ_author_name
'Takuya Kochi'
'Tony P. Tang'
'Jonathan A. Ellman'
_publ_section_title
;
 Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6518
_journal_page_last               6519
_journal_paper_doi               10.1021/ja026292g
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C19 H24 N O3 S '
_chemical_formula_sum            'C19 H24 N O3 S'
_chemical_formula_weight         346.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             'Tue Jan 15 10:53:09 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8532(8)
_cell_length_b                   11.640(2)
_cell_length_c                   26.638(3)
_cell_measurement_reflns_used    1602
_cell_measurement_temperature    133.2
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      1.8
_cell_volume                     1814.9(4)
_computing_cell_refinement       'Bruker SAINT v5.04'
_computing_data_collection       'Bruker SMART v5.0'
_computing_data_reduction        'Bruker SAINT v5.04'
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SIR97
_diffrn_measured_fraction_theta_full 1.6321
_diffrn_measured_fraction_theta_max 1.6321
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            3002
_diffrn_reflns_theta_full        24.73
_diffrn_reflns_theta_max         24.73
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1959
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00022|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0469
_reflns_number_gt                1959
_reflns_number_total             2977
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja026292g_s2_2.cif
_cod_data_source_block           syn-4e
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C19 H24 N O3 S '
_cod_database_code               4114859
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
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_calc_flag
S1 S 0.2809(2) 0.54211(9) 0.25960(4) 0.0238(3) Uani 1.00 d
O1 O 0.0934(5) 0.6090(3) 0.23433(10) 0.0363(9) Uani 1.00 d
O2 O -0.1118(5) 0.2844(3) 0.3288(1) 0.0311(10) Uani 1.00 d
N1 N 0.1579(6) 0.4696(3) 0.3055(1) 0.024(1) Uani 1.00 d
C1 C 0.3590(7) 0.4316(3) 0.2135(1) 0.018(1) Uani 1.00 d
C2 C 0.4875(8) 0.4982(4) 0.1726(2) 0.032(1) Uani 1.00 d
C3 C 0.1503(7) 0.3731(4) 0.1923(2) 0.035(2) Uani 1.00 d
C4 C 0.5169(8) 0.3478(4) 0.2389(2) 0.035(1) Uani 1.00 d
C5 C 0.2877(7) 0.4497(4) 0.3521(1) 0.022(1) Uani 1.00 d
C6 C 0.1417(7) 0.3737(3) 0.3872(1) 0.020(1) Uani 1.00 d
C7 C 0.0569(7) 0.2598(4) 0.3663(1) 0.022(1) Uani 1.00 d
C8 C 0.3445(7) 0.5624(4) 0.3782(1) 0.019(1) Uani 1.00 d
C9 C 0.1877(8) 0.6509(4) 0.3807(2) 0.028(1) Uani 1.00 d
C10 C 0.2373(9) 0.7486(4) 0.4081(2) 0.034(1) Uani 1.00 d
C11 C 0.4425(9) 0.7604(4) 0.4330(2) 0.035(2) Uani 1.00 d
C12 C 0.5977(8) 0.6746(5) 0.4300(2) 0.036(2) Uani 1.00 d
C13 C 0.5516(8) 0.5751(4) 0.4026(2) 0.031(1) Uani 1.00 d
C14 C -0.0437(7) 0.1853(3) 0.4073(1) 0.019(1) Uani 1.00 d
C15 C -0.2535(8) 0.2131(4) 0.4284(1) 0.030(1) Uani 1.00 d
C16 C -0.3440(8) 0.1474(5) 0.4667(2) 0.040(2) Uani 1.00 d
C17 C -0.2283(10) 0.0509(4) 0.4836(2) 0.042(2) Uani 1.00 d
C18 C -0.0191(10) 0.0235(4) 0.4631(2) 0.042(2) Uani 1.00 d
C19 C 0.0708(8) 0.0901(4) 0.4250(1) 0.029(1) Uani 1.00 d
H1 H 0.3862 0.5508 0.1568 0.0390 Uiso 1.00 calc
H2 H 0.6109 0.5392 0.1873 0.0390 Uiso 1.00 calc
H3 H 0.5451 0.4459 0.1483 0.0390 Uiso 1.00 calc
H4 H 0.1960 0.3174 0.1682 0.0414 Uiso 1.00 calc
H5 H 0.0689 0.3364 0.2187 0.0414 Uiso 1.00 calc
H6 H 0.0549 0.4285 0.1767 0.0414 Uiso 1.00 calc
H7 H 0.6412 0.3882 0.2535 0.0425 Uiso 1.00 calc
H8 H 0.4360 0.3076 0.2643 0.0425 Uiso 1.00 calc
H9 H 0.5735 0.2945 0.2149 0.0425 Uiso 1.00 calc
H10 H 0.4255 0.4105 0.3443 0.0261 Uiso 1.00 calc
H11 H 0.2312 0.3573 0.4161 0.0237 Uiso 1.00 calc
H12 H 0.0114 0.4172 0.3967 0.0237 Uiso 1.00 calc
H13 H 0.1811 0.2203 0.3512 0.0263 Uiso 1.00 calc
H14 H 0.0459 0.6447 0.3636 0.0334 Uiso 1.00 calc
H15 H 0.1278 0.8087 0.4099 0.0413 Uiso 1.00 calc
H16 H 0.4743 0.8277 0.4519 0.0415 Uiso 1.00 calc
H17 H 0.7401 0.6822 0.4468 0.0433 Uiso 1.00 calc
H18 H 0.6629 0.5159 0.4007 0.0372 Uiso 1.00 calc
H19 H -0.3354 0.2779 0.4165 0.0361 Uiso 1.00 calc
H20 H -0.4858 0.1683 0.4814 0.0475 Uiso 1.00 calc
H21 H -0.2927 0.0040 0.5091 0.0508 Uiso 1.00 calc
H22 H 0.0632 -0.0411 0.4751 0.0509 Uiso 1.00 calc
H23 H 0.2140 0.0699 0.4107 0.0343 Uiso 1.00 calc
H24 H 0.066(7) 0.420(4) 0.298(2) 0.0405 Uiso 1.00 calc
H25 H -0.105(7) 0.231(4) 0.307(2) 0.0405 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 N1 106.1(2)
O1 S1 C1 104.1(2)
N1 S1 C1 104.2(2)
S1 N1 C5 118.7(3)
S1 C1 C2 104.0(3)
S1 C1 C3 111.4(3)
S1 C1 C4 107.8(3)
C2 C1 C3 111.1(3)
C2 C1 C4 110.2(3)
C3 C1 C4 111.9(3)
N1 C5 C6 108.4(3)
N1 C5 C8 111.2(3)
C6 C5 C8 109.7(3)
C5 C6 C7 117.3(3)
O2 C7 C6 107.8(3)
O2 C7 C14 110.5(3)
C6 C7 C14 111.2(3)
C5 C8 C9 121.3(3)
C5 C8 C13 119.9(4)
C9 C8 C13 118.7(4)
C8 C9 C10 120.0(4)
C9 C10 C11 121.2(5)
C10 C11 C12 118.9(4)
C11 C12 C13 120.9(4)
C8 C13 C12 120.3(4)
C7 C14 C15 120.2(4)
C7 C14 C19 121.2(4)
C15 C14 C19 118.6(4)
C14 C15 C16 120.7(4)
C15 C16 C17 120.1(4)
C16 C17 C18 119.5(4)
C17 C18 C19 120.0(4)
C14 C19 C18 121.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 1.504(3) yes
S1 N1 1.650(4) yes
S1 C1 1.837(4) yes
O2 C7 1.435(4) yes
N1 C5 1.475(5) yes
C1 C2 1.534(5) yes
C1 C3 1.508(5) yes
C1 C4 1.505(5) yes
C5 C6 1.544(5) yes
C5 C8 1.522(5) yes
C6 C7 1.521(5) yes
C7 C14 1.514(5) yes
C8 C9 1.381(5) yes
C8 C13 1.383(6) yes
C9 C10 1.382(6) yes
C10 C11 1.378(6) yes
C11 C12 1.352(7) yes
C12 C13 1.395(6) yes
C14 C15 1.389(6) yes
C14 C19 1.378(5) yes
C15 C16 1.379(6) yes
C16 C17 1.387(7) yes
C17 C18 1.378(7) yes
C18 C19 1.381(6) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 O2 2.647(4) 4_555
O1 C7 3.323(5) 4_555
O2 C4 3.316(5) 1_455
O2 N1 2.744(4) .
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
S1 N1 C5 C6 -176.3(3)
S1 N1 C5 C8 63.0(4)
O1 S1 N1 C5 -146.3(3)
O1 S1 C1 C2 72.6(3)
O1 S1 C1 C3 -47.2(3)
O1 S1 C1 C4 -170.3(3)
O2 C7 C6 C5 -69.6(4)
O2 C7 C14 C15 -47.3(5)
O2 C7 C14 C19 133.5(4)
N1 S1 C1 C2 -176.3(3)
N1 S1 C1 C3 63.9(3)
N1 S1 C1 C4 -59.3(3)
N1 C5 C6 C7 55.1(4)
N1 C5 C8 C9 40.3(5)
N1 C5 C8 C13 -143.5(4)
C1 S1 N1 C5 104.1(3)
C5 C6 C7 C14 169.2(3)
C5 C8 C9 C10 174.8(3)
C5 C8 C13 C12 -174.8(4)
C6 C5 C8 C9 -79.6(4)
C6 C5 C8 C13 96.6(4)
C6 C7 C14 C15 72.3(5)
C6 C7 C14 C19 -106.8(4)
C7 C6 C5 C8 176.7(3)
C7 C14 C15 C16 -178.4(4)
C7 C14 C19 C18 178.7(4)
C8 C9 C10 C11 0.6(7)
C8 C13 C12 C11 -0.5(7)
C9 C8 C13 C12 1.4(6)
C9 C10 C11 C12 0.4(7)
C10 C9 C8 C13 -1.5(6)
C10 C11 C12 C13 -0.4(7)
C14 C15 C16 C17 -1.6(7)
C14 C19 C18 C17 1.1(7)
C15 C14 C19 C18 -0.5(6)
C15 C16 C17 C18 2.2(7)
C16 C15 C14 C19 0.7(6)
C16 C17 C18 C19 -1.9(7)
