#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:06:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180374 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204348.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_7204348
loop_
_publ_author_name
'Hou, Xue-Long'
'Luo, Yu-Mei'
'Yuan, Ke'
'Dai, Li-Xin'
_publ_section_title
;
 Reaction of α-carbanion of imines with N-tosylimines: a facile route
 to β-aminoaldehydes and 1,3-diamines
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1487
_journal_paper_doi               10.1039/b200198e
_journal_year                    2002
_chemical_formula_sum            'C19 H23 N O3 S'
_chemical_formula_weight         345.44
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.097(2)
_cell_angle_beta                 99.529(2)
_cell_angle_gamma                91.423(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4619(11)
_cell_length_b                   9.8687(12)
_cell_length_c                   10.1330(12)
_cell_measurement_reflns_used    588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.85
_cell_measurement_theta_min      2.74
_cell_volume                     917.26(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.1439
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4855
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4627
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0,2
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.646
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.646
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0055P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                1338
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b200198e.txt
_cod_data_source_block           cd21148
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7204348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.67656(9) 0.82644(8) 0.64633(7) 0.0571(2) Uani 1 1 d . . .
O1 O 0.53162(19) 0.81429(19) 0.57379(16) 0.0718(6) Uani 1 1 d . . .
O2 O 0.7184(2) 0.93171(18) 0.76489(17) 0.0715(6) Uani 1 1 d . . .
O3 O 0.8998(2) 1.1542(2) 0.43714(17) 0.0695(6) Uani 1 1 d . . .
N N 0.7767(3) 0.8528(3) 0.5373(2) 0.0552(7) Uani 1 1 d . . .
C1 C 0.7286(3) 0.8231(3) 0.3881(3) 0.0513(8) Uani 1 1 d . . .
C2 C 0.8183(3) 0.9229(3) 0.3314(2) 0.0473(8) Uani 1 1 d . . .
C3 C 0.7793(3) 0.9119(3) 0.1759(3) 0.0556(8) Uani 1 1 d . . .
C4 C 0.6272(4) 0.9485(6) 0.1279(4) 0.0844(13) Uani 1 1 d . . .
C5 C 0.8871(5) 0.9968(5) 0.1252(4) 0.0749(12) Uani 1 1 d . . .
C6 C 0.8020(4) 1.0680(3) 0.4016(3) 0.0573(9) Uani 1 1 d . . .
C7 C 0.7362(3) 0.6737(3) 0.3241(3) 0.0518(8) Uani 1 1 d . . .
C8 C 0.8584(4) 0.6036(4) 0.3463(3) 0.0648(9) Uani 1 1 d . . .
C9 C 0.8624(5) 0.4667(4) 0.2886(4) 0.0832(11) Uani 1 1 d . . .
C10 C 0.7422(6) 0.3995(5) 0.2077(4) 0.0939(14) Uani 1 1 d . . .
C11 C 0.6206(5) 0.4677(5) 0.1831(4) 0.0880(13) Uani 1 1 d . . .
C12 C 0.6167(4) 0.6042(4) 0.2400(3) 0.0698(10) Uani 1 1 d . . .
C13 C 0.7181(3) 0.6690(3) 0.6966(3) 0.0475(7) Uani 1 1 d . . .
C14 C 0.7832(3) 0.6669(4) 0.8287(3) 0.0650(9) Uani 1 1 d . . .
C15 C 0.8145(4) 0.5438(4) 0.8687(4) 0.0768(11) Uani 1 1 d . . .
C16 C 0.7844(3) 0.4197(3) 0.7808(4) 0.0671(9) Uani 1 1 d . . .
C17 C 0.7196(4) 0.4239(4) 0.6493(4) 0.0692(10) Uani 1 1 d . . .
C18 C 0.6860(3) 0.5459(4) 0.6070(3) 0.0630(9) Uani 1 1 d . . .
C19 C 0.8198(3) 0.2852(3) 0.8248(3) 0.1068(12) Uani 1 1 d . . .
H20 H 0.9204 0.2720 0.8273 0.160 Uiso 1 1 calc R . .
H21 H 0.7650 0.2112 0.7615 0.160 Uiso 1 1 calc R . .
H22 H 0.7969 0.2865 0.9138 0.160 Uiso 1 1 calc R . .
H1 H 0.626(2) 0.851(2) 0.3791(18) 0.044(7) Uiso 1 1 d . . .
H2 H 0.914(2) 0.908(2) 0.3552(17) 0.032(7) Uiso 1 1 d . . .
H3 H 0.786(2) 0.810(2) 0.138(2) 0.053(8) Uiso 1 1 d . . .
H4 H 0.552(3) 0.884(3) 0.154(3) 0.139(16) Uiso 1 1 d . . .
H5 H 0.611(3) 0.930(3) 0.032(3) 0.104(12) Uiso 1 1 d . . .
H6 H 0.614(4) 1.046(3) 0.164(3) 0.136(18) Uiso 1 1 d . . .
H7 H 0.864(2) 0.986(2) 0.032(2) 0.056(8) Uiso 1 1 d . . .
H8 H 0.886(3) 1.094(3) 0.167(2) 0.087(12) Uiso 1 1 d . . .
H9 H 0.989(4) 0.974(3) 0.145(3) 0.144(17) Uiso 1 1 d . . .
H10 H 0.695(2) 1.092(2) 0.422(2) 0.074(9) Uiso 1 1 d . . .
H11 H 0.940(3) 0.652(2) 0.397(2) 0.072(10) Uiso 1 1 d . . .
H12 H 0.949(3) 0.417(3) 0.311(2) 0.066(10) Uiso 1 1 d . . .
H13 H 0.741(3) 0.307(3) 0.170(3) 0.083(12) Uiso 1 1 d . . .
H14 H 0.539(3) 0.423(3) 0.124(2) 0.080(11) Uiso 1 1 d . . .
H15 H 0.530(2) 0.658(2) 0.229(2) 0.061(9) Uiso 1 1 d . . .
H16 H 0.807(2) 0.750(2) 0.894(2) 0.062(9) Uiso 1 1 d . . .
H17 H 0.852(3) 0.543(3) 0.953(2) 0.086(12) Uiso 1 1 d . . .
H18 H 0.701(2) 0.339(2) 0.589(2) 0.066(9) Uiso 1 1 d . . .
H19 H 0.635(2) 0.555(2) 0.517(2) 0.065(9) Uiso 1 1 d . . .
H23 H 0.860(3) 0.851(3) 0.566(2) 0.067(11) Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S O1 120.06(12) . . ?
O2 S N 106.97(12) . . ?
O1 S N 105.78(12) . . ?
O2 S C13 106.60(12) . . ?
O1 S C13 108.66(13) . . ?
N S C13 108.34(13) . . ?
C1 N S 124.0(2) . . ?
N C1 C7 113.9(2) . . ?
N C1 C2 105.7(2) . . ?
C7 C1 C2 113.7(2) . . ?
C6 C2 C1 109.0(2) . . ?
C6 C2 C3 110.0(2) . . ?
C1 C2 C3 113.6(2) . . ?
C5 C3 C4 111.3(3) . . ?
C5 C3 C2 110.3(3) . . ?
C4 C3 C2 113.8(3) . . ?
O3 C6 C2 123.6(3) . . ?
C8 C7 C12 118.3(3) . . ?
C8 C7 C1 122.2(3) . . ?
C12 C7 C1 119.6(3) . . ?
C7 C8 C9 121.2(4) . . ?
C10 C9 C8 119.5(4) . . ?
C11 C10 C9 120.1(4) . . ?
C10 C11 C12 120.5(4) . . ?
C11 C12 C7 120.4(4) . . ?
C18 C13 C14 118.8(3) . . ?
C18 C13 S 121.3(2) . . ?
C14 C13 S 119.9(2) . . ?
C15 C14 C13 120.1(3) . . ?
C14 C15 C16 122.2(3) . . ?
C15 C16 C17 116.9(3) . . ?
C15 C16 C19 122.0(3) . . ?
C17 C16 C19 121.1(3) . . ?
C18 C17 C16 122.0(3) . . ?
C17 C18 C13 120.0(3) . . ?
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
S O2 1.4366(16) . ?
S O1 1.4362(17) . ?
S N 1.619(2) . ?
S C13 1.752(3) . ?
O3 C6 1.205(3) . ?
N C1 1.480(3) . ?
C1 C7 1.512(4) . ?
C1 C2 1.529(4) . ?
C2 C6 1.507(4) . ?
C2 C3 1.542(3) . ?
C3 C5 1.512(4) . ?
C3 C4 1.514(4) . ?
C7 C8 1.368(4) . ?
C7 C12 1.383(4) . ?
C8 C9 1.379(4) . ?
C9 C10 1.367(5) . ?
C10 C11 1.356(5) . ?
C11 C12 1.373(5) . ?
C13 C18 1.377(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.371(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.380(4) . ?
C16 C19 1.501(4) . ?
C17 C18 1.375(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S N C1 -146.9(2) . . . . ?
O1 S N C1 -17.8(3) . . . . ?
C13 S N C1 98.5(3) . . . . ?
S N C1 C7 -81.9(3) . . . . ?
S N C1 C2 152.6(2) . . . . ?
N C1 C2 C6 -54.6(3) . . . . ?
C7 C1 C2 C6 179.7(2) . . . . ?
N C1 C2 C3 -177.7(2) . . . . ?
C7 C1 C2 C3 56.7(3) . . . . ?
C6 C2 C3 C5 66.4(4) . . . . ?
C1 C2 C3 C5 -171.1(3) . . . . ?
C6 C2 C3 C4 -59.5(4) . . . . ?
C1 C2 C3 C4 63.0(4) . . . . ?
C1 C2 C6 O3 139.5(3) . . . . ?
C3 C2 C6 O3 -95.3(3) . . . . ?
N C1 C7 C8 -52.0(4) . . . . ?
C2 C1 C7 C8 69.2(3) . . . . ?
N C1 C7 C12 128.2(3) . . . . ?
C2 C1 C7 C12 -110.6(3) . . . . ?
C12 C7 C8 C9 -1.2(4) . . . . ?
C1 C7 C8 C9 179.0(3) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C11 0.9(6) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C8 C7 C12 C11 1.5(5) . . . . ?
C1 C7 C12 C11 -178.7(3) . . . . ?
O2 S C13 C18 177.5(2) . . . . ?
O1 S C13 C18 46.8(3) . . . . ?
N S C13 C18 -67.7(3) . . . . ?
O2 S C13 C14 -1.9(3) . . . . ?
O1 S C13 C14 -132.6(2) . . . . ?
N S C13 C14 112.9(2) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
S C13 C14 C15 179.3(3) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C14 C15 C16 C19 179.5(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C19 C16 C17 C18 179.8(3) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C14 C13 C18 C17 -0.5(4) . . . . ?
S C13 C18 C17 -179.9(2) . . . . ?
