#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/77/2217745.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_2217745
loop_
_publ_author_name
'Cui, Yongliang'
'Liu, Lei'
'Liu, Ming'
'Duan, Yousheng'
'Liu, Shangzhong'
_publ_section_title
;
 4-(5-tert-Butyl-1,3-dithian-2-yl)-5-chloro-2-phenyl-1,3-oxazole
;
_journal_coeditor_code           CV2381
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o543
_journal_paper_doi               10.1107/S1600536808002821
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H20 Cl N O S2'
_chemical_formula_moiety         'C17 H20 Cl N O S2'
_chemical_formula_sum            'C17 H20 Cl N O S2'
_chemical_formula_weight         353.91
_chemical_name_systematic
;
4-(5-tert-Butyl-1,3-dithian-2-yl)-5-chloro-2-phenyl-1,3-oxazole
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4543(15)
_cell_length_b                   26.222(5)
_cell_length_c                   9.4772(19)
_cell_measurement_reflns_used    13320
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1792.7(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5683
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.9239
_exptl_absorpt_correction_T_min  0.8629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0497
_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)+(0.0651P)²+0.55P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2788
_reflns_number_total             3135
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2381.cif
_cod_data_source_block           I
_cod_original_cell_volume        1792.7(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217745
_cod_database_fobs_code          2217745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
S S1 0.21531(9) 0.68715(2) 0.75838(9) 0.0672(2) Uani d U 1
S S2 0.56576(9) 0.74615(2) 0.89160(8) 0.0656(2) Uani d U 1
Cl Cl1 0.74022(11) 0.62257(3) 0.61190(8) 0.0840(3) Uani d U 1
O O1 0.7196(2) 0.57469(6) 0.84876(18) 0.0576(4) Uani d U 1
N N1 0.5427(3) 0.62247(7) 0.9549(2) 0.0541(5) Uani d U 1
C C1 0.6072(4) 0.54919(11) 1.1975(3) 0.0732(7) Uani d U 1
H H1B 0.5353 0.5776 1.2042 0.088 Uiso calc R 1
C C2 0.6441(5) 0.51328(13) 1.3080(4) 0.0923(10) Uani d U 1
H H2A 0.5966 0.5174 1.3891 0.111 Uiso calc R 1
C C3 0.7516(6) 0.47136(13) 1.2970(4) 0.0978(11) Uani d U 1
H H3A 0.7789 0.4476 1.3723 0.117 Uiso calc R 1
C C4 0.8183(5) 0.46438(12) 1.1775(4) 0.0869(9) Uani d U 1
H H4A 0.8881 0.4355 1.1703 0.104 Uiso calc R 1
C C5 0.7828(4) 0.49976(10) 1.0678(3) 0.0685(7) Uani d U 1
H H5A 0.8293 0.4950 0.9865 0.082 Uiso calc R 1
C C6 0.6776(3) 0.54266(9) 1.0775(3) 0.0557(6) Uani d U 1
C C7 0.6401(3) 0.58120(9) 0.9633(3) 0.0530(5) Uani d U 1
C C8 0.6628(3) 0.61672(10) 0.7651(3) 0.0567(6) Uani d U 1
C C9 0.5551(3) 0.64573(9) 0.8256(2) 0.0523(5) Uani d U 1
C C10 0.4602(3) 0.69455(9) 0.7721(3) 0.0523(5) Uani d U 1
H H10A 0.4767 0.7014 0.6744 0.063 Uiso calc R 1
C C11 0.1332(4) 0.75009(9) 0.6948(3) 0.0619(6) Uani d U 1
H H11A 0.1585 0.7558 0.6006 0.074 Uiso calc R 1
H H11B -0.0002 0.7511 0.6810 0.074 Uiso calc R 1
C C12 0.2190(3) 0.79347(9) 0.7963(2) 0.0490(5) Uani d U 1
H H12A 0.2133 0.7835 0.8948 0.059 Uiso calc R 1
C C13 0.4239(3) 0.79820(9) 0.7989(3) 0.0598(6) Uani d U 1
H H13A 0.4711 0.8300 0.8465 0.072 Uiso calc R 1
H H13B 0.4354 0.7999 0.6993 0.072 Uiso calc R 1
C C14 0.1074(4) 0.84396(9) 0.7598(3) 0.0573(6) Uani d U 1
C C15 -0.0878(4) 0.83563(13) 0.7799(4) 0.0839(9) Uani d U 1
H H15A -0.1582 0.8665 0.7568 0.126 Uiso calc R 1
H H15B -0.0799 0.8263 0.8793 0.126 Uiso calc R 1
H H15C -0.1478 0.8088 0.7163 0.126 Uiso calc R 1
C C16 0.0952(4) 0.86200(12) 0.6043(3) 0.0718(8) Uani d U 1
H H16A 0.0248 0.8930 0.5861 0.108 Uiso calc R 1
H H16B 0.0353 0.8363 0.5365 0.108 Uiso calc R 1
H H16C 0.2177 0.8680 0.5927 0.108 Uiso calc R 1
C C17 0.2000(5) 0.88590(11) 0.8662(4) 0.0872(9) Uani d U 1
H H17A 0.1309 0.9170 0.8433 0.131 Uiso calc R 1
H H17B 0.3244 0.8912 0.8580 0.131 Uiso calc R 1
H H17C 0.2026 0.8758 0.9641 0.131 Uiso calc R 1
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'
Cl Cl 0.1484 0.1585 '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
C10 S1 C11 100.18(12)
C10 S2 C13 98.67(12)
C8 O1 C7 103.14(18)
C7 N1 C9 105.1(2)
C6 C1 C2 119.7(3)
C6 C1 H1B 120.1
C2 C1 H1B 120.1
C3 C2 C1 119.6(3)
C3 C2 H2A 120.2
C1 C2 H2A 120.2
C4 C3 C2 120.8(3)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 120.0(3)
C3 C4 H4A 120.0
C5 C4 H4A 120.0
C4 C5 C6 120.2(3)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C1 C6 C5 119.6(3)
C1 C6 C7 119.0(2)
C5 C6 C7 121.3(2)
N1 C7 O1 113.7(2)
N1 C7 C6 128.8(2)
O1 C7 C6 117.5(2)
C9 C8 O1 110.1(2)
C9 C8 Cl1 133.3(2)
O1 C8 Cl1 116.62(18)
C8 C9 N1 108.0(2)
C8 C9 C10 129.0(2)
N1 C9 C10 123.0(2)
C9 C10 S1 108.47(16)
C9 C10 S2 109.57(17)
S1 C10 S2 113.36(13)
C9 C10 H10A 108.4
S1 C10 H10A 108.4
S2 C10 H10A 108.4
C12 C11 S1 114.70(17)
C12 C11 H11A 108.6
S1 C11 H11A 108.6
C12 C11 H11B 108.6
S1 C11 H11B 108.6
H11A C11 H11B 107.6
C11 C12 C13 109.28(19)
C11 C12 C14 112.3(2)
C13 C12 C14 114.3(2)
C11 C12 H12A 106.9
C13 C12 H12A 106.9
C14 C12 H12A 106.9
C12 C13 S2 113.93(17)
C12 C13 H13A 108.8
S2 C13 H13A 108.8
C12 C13 H13B 108.8
S2 C13 H13B 108.8
H13A C13 H13B 107.7
C16 C14 C15 109.7(2)
C16 C14 C17 108.7(2)
C15 C14 C17 107.7(2)
C16 C14 C12 112.15(19)
C15 C14 C12 108.8(2)
C17 C14 C12 109.7(2)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.808(3)
S1 C11 1.810(3)
S2 C10 1.812(2)
S2 C13 1.813(3)
Cl1 C8 1.699(3)
O1 C8 1.362(3)
O1 C7 1.372(3)
N1 C7 1.294(3)
N1 C9 1.393(3)
C1 C6 1.378(4)
C1 C2 1.383(4)
C1 H1B 0.9300
C2 C3 1.380(5)
C2 H2A 0.9300
C3 C4 1.359(5)
C3 H3A 0.9300
C4 C5 1.369(4)
C4 H4A 0.9300
C5 C6 1.387(4)
C5 H5A 0.9300
C6 C7 1.455(3)
C8 C9 1.335(3)
C9 C10 1.489(3)
C10 H10A 0.9800
C11 C12 1.523(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.526(3)
C12 C14 1.556(3)
C12 H12A 0.9800
C13 H13A 0.9700
C13 H13B 0.9700
C14 C16 1.528(3)
C14 C15 1.530(4)
C14 C17 1.534(4)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C6 C1 C2 C3 0.3(5)
C1 C2 C3 C4 -1.5(6)
C2 C3 C4 C5 1.6(6)
C3 C4 C5 C6 -0.5(5)
C2 C1 C6 C5 0.8(4)
C2 C1 C6 C7 -179.0(3)
C4 C5 C6 C1 -0.7(4)
C4 C5 C6 C7 179.1(3)
C9 N1 C7 O1 0.4(3)
C9 N1 C7 C6 178.9(2)
C8 O1 C7 N1 0.2(3)
C8 O1 C7 C6 -178.5(2)
C1 C6 C7 N1 -1.5(4)
C5 C6 C7 N1 178.6(2)
C1 C6 C7 O1 177.0(2)
C5 C6 C7 O1 -2.9(3)
C7 O1 C8 C9 -0.7(3)
C7 O1 C8 Cl1 178.63(17)
O1 C8 C9 N1 1.0(3)
Cl1 C8 C9 N1 -178.2(2)
O1 C8 C9 C10 -179.1(2)
Cl1 C8 C9 C10 1.8(4)
C7 N1 C9 C8 -0.8(3)
C7 N1 C9 C10 179.2(2)
C8 C9 C10 S1 124.2(3)
N1 C9 C10 S1 -55.9(3)
C8 C9 C10 S2 -111.6(3)
N1 C9 C10 S2 68.4(3)
C11 S1 C10 C9 179.42(16)
C11 S1 C10 S2 57.48(16)
C13 S2 C10 C9 179.80(17)
C13 S2 C10 S1 -58.88(15)
C10 S1 C11 C12 -59.4(2)
S1 C11 C12 C13 67.9(2)
S1 C11 C12 C14 -164.19(16)
C11 C12 C13 S2 -70.4(2)
C14 C12 C13 S2 162.84(16)
C10 S2 C13 C12 63.2(2)
C11 C12 C14 C16 -59.6(3)
C13 C12 C14 C16 65.6(3)
C11 C12 C14 C15 62.0(3)
C13 C12 C14 C15 -172.8(2)
C11 C12 C14 C17 179.6(2)
C13 C12 C14 C17 -55.2(3)
