#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/12/2201267.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201267
loop_
_publ_author_name
'Clegg, William'
'Horsburgh, Lynne'
_publ_section_title
;
 (4S,5S)-2-Benzyloxy-4-methyl-5-(4-tolylthiocarbonyl)oxazoline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o767
_journal_page_last               o768
_journal_paper_doi               10.1107/S1600536802010759
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C19 H19 N O3 S'
_chemical_formula_moiety         'C19 H19 N O3 S'
_chemical_formula_sum            'C19 H19 N O3 S'
_chemical_formula_weight         341.41
_chemical_name_systematic
;
(4S,5S)-2-Benzyloxy-4-methyl-5-(4-tolylthiocarbonyl)oxazoline
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 109.043(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.9010(9)
_cell_length_b                   5.7705(4)
_cell_length_c                   13.7964(10)
_cell_measurement_reflns_used    6005
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.7
_cell_volume                     895.61(11)
_computing_cell_refinement       'local programs'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Siemens SMART 1K CCD'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6725
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.7
_diffrn_reflns_theta_min         1.8
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(XPREP in SHELXTL; Sheldrick, 1994)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.190
_refine_ls_abs_structure_details 'Flack (1983), 1056 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0300
_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)+(0.0493P)²+0.0826P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                3203
_reflns_number_total             3382
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2201267
_cod_database_fobs_code          2201267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.77056(9) 0.15718(19) 0.88474(9) 0.0315(3) Uani d . 1 . . O
C1 0.80856(12) 0.3805(3) 0.90228(10) 0.0250(3) Uani d . 1 . . C
N1 0.75829(11) 0.5210(2) 0.94457(9) 0.0281(3) Uani d . 1 . . N
C2 0.66024(12) 0.3912(3) 0.96289(10) 0.0257(3) Uani d . 1 . . C
H2 0.6778 0.3730 1.0385 0.031 Uiso calc R 1 . . H
C3 0.66524(12) 0.1468(3) 0.91457(11) 0.0263(3) Uani d . 1 . . C
H3 0.6751 0.0242 0.9679 0.032 Uiso calc R 1 . . H
C4 0.55805(12) 0.0917(3) 0.82225(10) 0.0251(3) Uani d . 1 . . C
O2 0.46249(9) 0.0483(2) 0.83037(8) 0.0302(2) Uani d . 1 . . O
C5 0.54399(14) 0.5225(3) 0.91859(12) 0.0322(3) Uani d . 1 . . C
H5A 0.5506 0.6741 0.9520 0.048 Uiso calc R 1 . . H
H5B 0.4794 0.4339 0.9305 0.048 Uiso calc R 1 . . H
H5C 0.5270 0.5441 0.8447 0.048 Uiso calc R 1 . . H
O3 0.90081(9) 0.4140(2) 0.86971(8) 0.0291(2) Uani d . 1 . . O
C6 0.95440(14) 0.6417(3) 0.89320(13) 0.0330(3) Uani d . 1 . . C
H6A 0.9910 0.6609 0.9683 0.040 Uiso calc R 1 . . H
H6B 0.8935 0.7637 0.8673 0.040 Uiso calc R 1 . . H
C7 1.04768(13) 0.6597(3) 0.84150(11) 0.0269(3) Uani d . 1 . . C
C8 1.12865(13) 0.4826(3) 0.84919(11) 0.0290(3) Uani d . 1 . . C
H8 1.1265 0.3482 0.8883 0.035 Uiso calc R 1 . . H
C9 1.21306(14) 0.5010(3) 0.79981(12) 0.0341(4) Uani d . 1 . . C
H9 1.2676 0.3781 0.8040 0.041 Uiso calc R 1 . . H
C10 1.21756(15) 0.7000(4) 0.74417(13) 0.0385(4) Uani d . 1 . . C
H10 1.2753 0.7133 0.7105 0.046 Uiso calc R 1 . . H
C11 1.13857(17) 0.8765(4) 0.73799(13) 0.0416(4) Uani d . 1 . . C
H11 1.1424 1.0130 0.7007 0.050 Uiso calc R 1 . . H
C12 1.05275(15) 0.8572(3) 0.78591(13) 0.0357(4) Uani d . 1 . . C
H12 0.9976 0.9794 0.7805 0.043 Uiso calc R 1 . . H
S1 0.58788(4) 0.10061(8) 0.70389(3) 0.03961(12) Uani d . 1 . . S
C13 0.44347(16) 0.0351(3) 0.61861(12) 0.0352(4) Uani d . 1 . . C
C14 0.42437(18) -0.1741(4) 0.56673(13) 0.0411(4) Uani d . 1 . . C
H14 0.4875 -0.2821 0.5772 0.049 Uiso calc R 1 . . H
C15 0.3119(2) -0.2245(4) 0.49909(13) 0.0472(5) Uani d . 1 . . C
H15 0.2988 -0.3679 0.4633 0.057 Uiso calc R 1 . . H
C16 0.2187(2) -0.0705(4) 0.48289(13) 0.0482(5) Uani d . 1 . . C
C17 0.23960(19) 0.1389(4) 0.53491(13) 0.0484(5) Uani d . 1 . . C
H17 0.1765 0.2470 0.5242 0.058 Uiso calc R 1 . . H
C18 0.35148(17) 0.1930(3) 0.60242(13) 0.0413(4) Uani d . 1 . . C
H18 0.3649 0.3375 0.6373 0.050 Uiso calc R 1 . . H
C19 0.0957(2) -0.1310(6) 0.41158(18) 0.0787(9) Uani d . 1 . . C
H19A 0.0615 -0.2533 0.4426 0.118 Uiso calc R 1 . . H
H19B 0.1011 -0.1857 0.3460 0.118 Uiso calc R 1 . . H
H19C 0.0449 0.0068 0.4000 0.118 Uiso calc R 1 . . H
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_publ_flag
C1 O1 C3 104.94(11) yes
O1 C1 N1 120.79(13) yes
O1 C1 O3 109.94(13) yes
N1 C1 O3 129.27(15) yes
C1 N1 C2 105.93(14) yes
N1 C2 H2 108.9 ?
N1 C2 C3 103.97(11) yes
N1 C2 C5 110.19(13) ?
H2 C2 C3 108.9 ?
H2 C2 C5 108.9 ?
C3 C2 C5 115.65(13) ?
O1 C3 C2 103.94(11) yes
O1 C3 H3 109.6 ?
O1 C3 C4 109.94(11) ?
C2 C3 H3 109.6 ?
C2 C3 C4 114.07(13) ?
H3 C3 C4 109.6 ?
C3 C4 O2 121.84(12) ?
C3 C4 S1 113.58(9) ?
O2 C4 S1 124.58(11) ?
C2 C5 H5A 109.5 ?
C2 C5 H5B 109.5 ?
C2 C5 H5C 109.5 ?
H5A C5 H5B 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C1 O3 C6 114.08(12) ?
O3 C6 H6A 110.3 ?
O3 C6 H6B 110.3 ?
O3 C6 C7 107.15(12) ?
H6A C6 H6B 108.5 ?
H6A C6 C7 110.3 ?
H6B C6 C7 110.3 ?
C6 C7 C8 121.00(14) ?
C6 C7 C12 119.38(14) ?
C8 C7 C12 119.62(14) ?
C7 C8 H8 119.9 ?
C7 C8 C9 120.16(15) ?
H8 C8 C9 119.9 ?
C8 C9 H9 120.1 ?
C8 C9 C10 119.84(16) ?
H9 C9 C10 120.1 ?
C9 C10 H10 120.0 ?
C9 C10 C11 119.91(15) ?
H10 C10 C11 120.0 ?
C10 C11 H11 119.8 ?
C10 C11 C12 120.43(17) ?
H11 C11 C12 119.8 ?
C7 C12 C11 120.02(16) ?
C7 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C4 S1 C13 99.31(7) ?
S1 C13 C14 119.21(15) ?
S1 C13 C18 120.61(14) ?
C14 C13 C18 120.16(17) ?
C13 C14 H14 120.3 ?
C13 C14 C15 119.3(2) ?
H14 C14 C15 120.3 ?
C14 C15 H15 119.3 ?
C14 C15 C16 121.35(18) ?
H15 C15 C16 119.3 ?
C15 C16 C17 118.56(18) ?
C15 C16 C19 120.8(2) ?
C17 C16 C19 120.7(2) ?
C16 C17 H17 119.5 ?
C16 C17 C18 120.9(2) ?
H17 C17 C18 119.5 ?
C13 C18 C17 119.66(18) ?
C13 C18 H18 120.2 ?
C17 C18 H18 120.2 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19B 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.361(2) yes
O1 C3 . 1.4424(16) yes
C1 N1 . 1.258(2) yes
C1 O3 . 1.3292(17) yes
N1 C2 . 1.4760(19) yes
C2 H2 . 1.000 ?
C2 C3 . 1.569(2) yes
C2 C5 . 1.520(2) ?
C3 H3 . 1.000 ?
C3 C4 . 1.513(2) ?
C4 O2 . 1.2048(16) ?
C4 S1 . 1.7815(13) ?
C5 H5A . 0.980 ?
C5 H5B . 0.980 ?
C5 H5C . 0.980 ?
O3 C6 . 1.4501(19) ?
C6 H6A . 0.990 ?
C6 H6B . 0.990 ?
C6 C7 . 1.5061(19) ?
C7 C8 . 1.385(2) ?
C7 C12 . 1.386(2) ?
C8 H8 . 0.950 ?
C8 C9 . 1.390(2) ?
C9 H9 . 0.950 ?
C9 C10 . 1.392(3) ?
C10 H10 . 0.950 ?
C10 C11 . 1.370(3) ?
C11 H11 . 0.950 ?
C11 C12 . 1.390(2) ?
C12 H12 . 0.950 ?
S1 C13 . 1.7781(18) ?
C13 C14 . 1.384(3) ?
C13 C18 . 1.385(3) ?
C14 H14 . 0.950 ?
C14 C15 . 1.390(3) ?
C15 H15 . 0.950 ?
C15 C16 . 1.382(3) ?
C16 C17 . 1.386(3) ?
C16 C19 . 1.514(3) ?
C17 H17 . 0.950 ?
C17 C18 . 1.389(3) ?
C18 H18 . 0.950 ?
C19 H19A . 0.980 ?
C19 H19B . 0.980 ?
C19 H19C . 0.980 ?
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_publ_flag
C3 O1 C1 N1 5.39(18) yes
C3 O1 C1 O3 -175.19(11) ?
O1 C1 N1 C2 -1.42(18) yes
O3 C1 N1 C2 179.28(14) ?
C1 N1 C2 C3 -2.87(15) yes
C1 N1 C2 C5 -127.40(14) ?
C1 O1 C3 C2 -6.31(14) yes
C1 O1 C3 C4 116.17(13) ?
N1 C2 C3 O1 5.71(14) yes
N1 C2 C3 C4 -114.00(13) ?
C5 C2 C3 O1 126.64(12) ?
C5 C2 C3 C4 6.93(17) ?
O1 C3 C4 O2 171.41(14) ?
O1 C3 C4 S1 -9.11(16) ?
C2 C3 C4 O2 -72.31(19) ?
C2 C3 C4 S1 107.17(12) ?
O1 C1 O3 C6 -174.87(12) ?
N1 C1 O3 C6 4.5(2) ?
C1 O3 C6 C7 -173.95(12) ?
O3 C6 C7 C8 -46.97(18) ?
O3 C6 C7 C12 133.39(15) ?
C6 C7 C8 C9 179.14(14) ?
C12 C7 C8 C9 -1.2(2) ?
C7 C8 C9 C10 1.3(2) ?
C8 C9 C10 C11 -0.2(2) ?
C9 C10 C11 C12 -0.8(3) ?
C6 C7 C12 C11 179.83(15) ?
C8 C7 C12 C11 0.2(2) ?
C10 C11 C12 C7 0.8(3) ?
C3 C4 S1 C13 -178.74(12) ?
O2 C4 S1 C13 0.73(17) ?
C4 S1 C13 C14 -111.95(13) ?
C4 S1 C13 C18 69.38(14) ?
S1 C13 C14 C15 -179.25(13) ?
C18 C13 C14 C15 -0.6(2) ?
C13 C14 C15 C16 -0.2(2) ?
C14 C15 C16 C17 0.7(3) ?
C14 C15 C16 C19 -178.03(18) ?
C15 C16 C17 C18 -0.4(3) ?
C19 C16 C17 C18 178.34(18) ?
S1 C13 C18 C17 179.53(13) ?
C14 C13 C18 C17 0.9(2) ?
C16 C17 C18 C13 -0.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24731656
