#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101762.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_8101762
loop_
_publ_author_name
'Herrera, A.'
'Martínez-Álvarez, R.'
'Ramiro, P.'
'Rosario Torres, M.'
_publ_section_title
;
Crystal structure of 5-methyl-4-(methylthio)-2-(4-nitrobenzyl)oxazole, 
C₁₂H₁₂N₂O₃S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              243
_journal_page_last               244
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C12 H12 N2 O3 S'
_chemical_formula_weight         264.30
_chemical_melting_point          366.1(10)
_chemical_name_systematic
; 
 5-methyl-4-(methylthio)-2-(4-nitrobenzyl)oxazole
;
_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                106.504(3)
_cell_angle_beta                 97.948(3)
_cell_angle_gamma                110.631(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1835(14)
_cell_length_b                   8.3545(14)
_cell_length_c                   10.5287(17)
_cell_measurement_temperature    293(2)
_cell_volume                     622.71(18)
_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 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       omega/phi
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4079
_diffrn_reflns_theta_full        28.93
_diffrn_reflns_theta_max         28.93
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.261
_refine_ls_shift/su_mean         0.036
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1640
_reflns_number_total             2870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1508.cff
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '92-94 \%C' was changed to
'366.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8101762
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18699(17) 0.91605(19) 0.87893(13) 0.0429(4) Uani 1 2 i d . . .
C2 C 0.0660(3) 0.9149(3) 0.7750(2) 0.0427(5) Uani 1 2 i d . . .
N3 N 0.0367(2) 1.0609(3) 0.80335(17) 0.0463(5) Uani 1 2 i d . . .
C4 C 0.1459(3) 1.1692(3) 0.9371(2) 0.0419(5) Uani 1 2 i d . . .
C5 C 0.2367(3) 1.0825(3) 0.9824(2) 0.0399(5) Uani 1 2 i d . . .
C6 C 0.3655(3) 1.1227(3) 1.1121(2) 0.0569(6) Uani 1 2 i d . . .
C8 C 0.2546(4) 1.5141(3) 0.9321(3) 0.0688(7) Uani 1 2 i d . . .
C9 C -0.0111(3) 0.7504(3) 0.6457(2) 0.0553(6) Uani 1 2 i d . . .
C1' C 0.1245(3) 0.7463(3) 0.5626(2) 0.0446(5) Uani 1 2 i d . . .
C2' C 0.2610(3) 0.6925(3) 0.5992(2) 0.0498(6) Uani 1 2 i d . . .
C3' C 0.3882(3) 0.6931(3) 0.5266(2) 0.0496(6) Uani 1 2 i d . . .
C4' C 0.3777(3) 0.7479(3) 0.4147(2) 0.0451(5) Uani 1 2 i d . . .
C5' C 0.2423(3) 0.7989(3) 0.3729(2) 0.0513(6) Uani 1 2 i d . . .
C6' C 0.1163(3) 0.7982(3) 0.4478(2) 0.0518(6) Uani 1 2 i d . . .
N10 N 0.5142(3) 0.7501(3) 0.3382(2) 0.0610(5) Uani 1 2 i d . . .
O11 O 0.6204(3) 0.6843(3) 0.3658(2) 0.0971(7) Uani 1 2 i d . . .
O12 O 0.5186(2) 0.8205(3) 0.25091(19) 0.0817(6) Uani 1 2 i d . . .
S7 S 0.14820(9) 1.38079(9) 1.02759(7) 0.0641(2) Uani 1 2 i d . . .
H2' H 0.2691 0.6535 0.6827 0.080 Uiso 1 2 i d . . .
H3' H 0.4815 0.6559 0.5563 0.080 Uiso 1 2 i d . . .
H5' H 0.2381 0.8495 0.2928 0.080 Uiso 1 2 i d . . .
H6' H 0.0226 0.8363 0.4229 0.080 Uiso 1 2 i d . . .
H6A H 0.4142 1.2565 1.1695 0.080 Uiso 1 2 i d . . .
H6B H 0.4780 1.1251 1.1018 0.080 Uiso 1 2 i d . . .
H6C H 0.3235 1.0415 1.1617 0.080 Uiso 1 2 i d . . .
H8A H 0.1835 1.4483 0.8264 0.080 Uiso 1 2 i d . . .
H8B H 0.2413 1.6303 0.9638 0.080 Uiso 1 2 i d . . .
H8C H 0.3828 1.5438 0.9388 0.080 Uiso 1 2 i d . . .
H9A H -0.1216 0.7658 0.5927 0.080 Uiso 1 2 i d . . .
H9B H -0.0437 0.6368 0.6741 0.080 Uiso 1 2 i 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
C5 O1 C2 104.62(16) . . ?
N3 C2 O1 113.81(19) . . ?
N3 C2 C9 128.9(2) . . ?
O1 C2 C9 117.24(19) . . ?
C2 N3 C4 104.38(17) . . ?
C5 C4 N3 109.85(18) . . ?
C5 C4 S7 127.33(17) . . ?
N3 C4 S7 122.76(15) . . ?
C4 C5 O1 107.34(17) . . ?
C4 C5 C6 135.1(2) . . ?
O1 C5 C6 117.51(19) . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 113.7 . . ?
H6A C6 H6B 95.0 . . ?
C5 C6 H6C 115.6 . . ?
H6A C6 H6C 114.2 . . ?
H6B C6 H6C 106.6 . . ?
S7 C8 H8A 109.8 . . ?
S7 C8 H8B 106.9 . . ?
H8A C8 H8B 106.4 . . ?
S7 C8 H8C 117.9 . . ?
H8A C8 H8C 107.7 . . ?
H8B C8 H8C 107.6 . . ?
C2 C9 C1' 112.07(17) . . ?
C2 C9 H9A 103.0 . . ?
C1' C9 H9A 111.1 . . ?
C2 C9 H9B 107.0 . . ?
C1' C9 H9B 107.5 . . ?
H9A C9 H9B 116.1 . . ?
C6' C1' C2' 118.6(2) . . ?
C6' C1' C9 120.6(2) . . ?
C2' C1' C9 120.9(2) . . ?
C3' C2' C1' 121.4(2) . . ?
C3' C2' H2' 118.8 . . ?
C1' C2' H2' 119.8 . . ?
C2' C3' C4' 118.6(2) . . ?
C2' C3' H3' 118.5 . . ?
C4' C3' H3' 122.9 . . ?
C3' C4' C5' 122.1(2) . . ?
C3' C4' N10 118.5(2) . . ?
C5' C4' N10 119.4(2) . . ?
C6' C5' C4' 118.4(2) . . ?
C6' C5' H5' 118.5 . . ?
C4' C5' H5' 122.8 . . ?
C5' C6' C1' 121.0(2) . . ?
C5' C6' H6' 120.4 . . ?
C1' C6' H6' 118.6 . . ?
O11 N10 O12 123.0(2) . . ?
O11 N10 C4' 118.8(2) . . ?
O12 N10 C4' 118.2(2) . . ?
C4 S7 C8 100.50(11) . . ?
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
O1 C5 1.379(2) . ?
O1 C2 1.366(2) . ?
C2 N3 1.286(3) . ?
C2 C9 1.493(3) . ?
N3 C4 1.399(2) . ?
C4 C5 1.335(3) . ?
C4 S7 1.746(2) . ?
C5 C6 1.477(3) . ?
C6 H6A 1.0043 . ?
C6 H6B 0.9362 . ?
C6 H6C 0.9681 . ?
C8 S7 1.790(2) . ?
C8 H8A 1.0620 . ?
C8 H8B 0.9827 . ?
C8 H8C 0.9761 . ?
C9 C1' 1.509(3) . ?
C9 H9A 1.0625 . ?
C9 H9B 1.0328 . ?
C1' C6' 1.396(3) . ?
C1' C2' 1.389(3) . ?
C2' C3' 1.374(3) . ?
C2' H2' 1.0226 . ?
C3' C4' 1.383(3) . ?
C3' H3' 0.9666 . ?
C4' C5' 1.381(3) . ?
C4' N10 1.462(3) . ?
C5' C6' 1.381(3) . ?
C5' H5' 1.0467 . ?
C6' H6' 0.9604 . ?
N10 O11 1.225(3) . ?
N10 O12 1.222(2) . ?
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
C5 O1 C2 N3 0.0(2) . . . . ?
C5 O1 C2 C9 179.05(17) . . . . ?
O1 C2 N3 C4 -0.2(2) . . . . ?
C9 C2 N3 C4 -179.1(2) . . . . ?
C2 N3 C4 C5 0.4(2) . . . . ?
C2 N3 C4 S7 -177.10(15) . . . . ?
N3 C4 C5 O1 -0.4(2) . . . . ?
S7 C4 C5 O1 176.96(13) . . . . ?
N3 C4 C5 C6 -178.2(2) . . . . ?
S7 C4 C5 C6 -0.9(4) . . . . ?
C2 O1 C5 C4 0.2(2) . . . . ?
C2 O1 C5 C6 178.52(17) . . . . ?
N3 C2 C9 C1' 104.9(3) . . . . ?
O1 C2 C9 C1' -74.0(2) . . . . ?
C2 C9 C1' C6' -101.6(2) . . . . ?
C2 C9 C1' C2' 77.7(3) . . . . ?
C6' C1' C2' C3' 1.2(3) . . . . ?
C9 C1' C2' C3' -178.2(2) . . . . ?
C1' C2' C3' C4' -0.3(3) . . . . ?
C2' C3' C4' C5' -1.1(3) . . . . ?
C2' C3' C4' N10 179.45(19) . . . . ?
C3' C4' C5' C6' 1.4(3) . . . . ?
N10 C4' C5' C6' -179.13(19) . . . . ?
C4' C5' C6' C1' -0.4(3) . . . . ?
C2' C1' C6' C5' -0.9(3) . . . . ?
C9 C1' C6' C5' 178.5(2) . . . . ?
C3' C4' N10 O11 8.1(3) . . . . ?
C5' C4' N10 O11 -171.4(2) . . . . ?
C3' C4' N10 O12 -170.7(2) . . . . ?
C5' C4' N10 O12 9.7(3) . . . . ?
C5 C4 S7 C8 113.9(2) . . . . ?
N3 C4 S7 C8 -69.13(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4481220
