#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239628.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_2239628
loop_
_publ_author_name
'Narayana, B.'
'Nayak, Prakash S.'
'Sarojini, Balladka K.'
'Jasinski, Jerry P.'
_publ_section_title
;
 2-(2-Methylphenyl)-N-(1,3-thiazol-2-yl)acetamide
;
_journal_coeditor_code           HB7232
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o716
_journal_paper_doi               10.1107/S1600536814011684
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H12 N2 O S'
_chemical_formula_moiety         'C12 H12 N2 O S'
_chemical_formula_sum            'C12 H12 N2 O S'
_chemical_formula_weight         232.30
_chemical_name_systematic
;
2-(2-Methylphenyl)-N-(1,3-thiazol-2-yl)acetamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.236(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6983(6)
_cell_length_b                   4.94078(13)
_cell_length_c                   14.4603(5)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.5140
_cell_measurement_theta_min      3.3550
_cell_volume                     1178.60(7)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Agilent (Eos, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7059
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.315
_diffrn_reflns_theta_min         5.363
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.281
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2012 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0401
_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)+(0.0678P)²+0.3670P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2065
_reflns_number_total             2250
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7232sup1.cif
_cod_data_source_block           I
_cod_database_code               2239628
_cod_database_fobs_code          2239628
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
S S1 0.51096(2) 1.09810(8) 0.33600(3) 0.02349(18) Uani d 1
O O1 0.66917(7) 0.9640(3) 0.43484(10) 0.0341(3) Uani d 1
N N1 0.58012(8) 0.6996(3) 0.47251(10) 0.0225(3) Uani d 1
H H1 0.5748 0.5659 0.5099 0.027 Uiso calc 1
N N2 0.43898(8) 0.7241(3) 0.39749(10) 0.0241(3) Uani d 1
C C1 0.51059(10) 0.8180(3) 0.40772(11) 0.0204(3) Uani d 1
C C2 0.38010(11) 0.8760(3) 0.32755(13) 0.0269(4) Uani d 1
H H2 0.3240 0.8362 0.3089 0.032 Uiso calc 1
C C3 0.40679(11) 1.0842(3) 0.28727(13) 0.0263(4) Uani d 1
H H3 0.3730 1.2055 0.2390 0.032 Uiso calc 1
C C4 0.65649(10) 0.7763(3) 0.48226(12) 0.0248(4) Uani d 1
C C5 0.72262(11) 0.6059(4) 0.55603(14) 0.0311(4) Uani d 1
H H5A 0.7121 0.5926 0.6186 0.037 Uiso calc 1
H H5B 0.7205 0.4206 0.5291 0.037 Uiso calc 1
C C6 0.80617(11) 0.7206(4) 0.57813(14) 0.0352(4) Uani d 1
C C7 0.85116(13) 0.6620(5) 0.51962(17) 0.0469(5) Uani d 1
C C8 0.92758(14) 0.7817(6) 0.5445(2) 0.0675(9) Uani d 1
H H8 0.9594 0.7420 0.5055 0.081 Uiso calc 1
C C9 0.95774(17) 0.9541(7) 0.6231(3) 0.0828(11) Uani d 1
H H9 1.0096 1.0343 0.6377 0.099 Uiso calc 1
C C10 0.91323(19) 1.0119(7) 0.6813(3) 0.0811(10) Uani d 1
H H10 0.9339 1.1318 0.7361 0.097 Uiso calc 1
C C11 0.83836(15) 0.8938(5) 0.6590(2) 0.0559(6) Uani d 1
H H11 0.8079 0.9311 0.6998 0.067 Uiso calc 1
C C12 0.81906(19) 0.4717(7) 0.4331(2) 0.0710(8) Uani d 1
H H12A 0.8022 0.3021 0.4550 0.106 Uiso calc 1
H H12B 0.8616 0.4343 0.4064 0.106 Uiso calc 1
H H12C 0.7724 0.5546 0.3814 0.106 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C3 S1 C1 88.70(8)
C1 N1 H1 117.9
C4 N1 H1 117.9
C4 N1 C1 124.11(14)
C1 N2 C2 109.46(14)
N1 C1 S1 123.41(12)
N2 C1 S1 115.48(12)
N2 C1 N1 121.11(14)
N2 C2 H2 121.9
C3 C2 N2 116.18(16)
C3 C2 H2 121.9
S1 C3 H3 124.9
C2 C3 S1 110.15(13)
C2 C3 H3 124.9
O1 C4 N1 122.06(15)
O1 C4 C5 124.26(15)
N1 C4 C5 113.67(14)
C4 C5 H5A 109.0
C4 C5 H5B 109.0
H5A C5 H5B 107.8
C6 C5 C4 112.79(14)
C6 C5 H5A 109.0
C6 C5 H5B 109.0
C7 C6 C5 121.9(2)
C7 C6 C11 119.3(2)
C11 C6 C5 118.73(19)
C6 C7 C8 118.1(3)
C6 C7 C12 120.8(2)
C8 C7 C12 121.2(2)
C7 C8 H8 119.1
C9 C8 C7 121.8(3)
C9 C8 H8 119.1
C8 C9 H9 120.0
C8 C9 C10 120.1(3)
C10 C9 H9 120.0
C9 C10 H10 120.5
C9 C10 C11 119.1(3)
C11 C10 H10 120.5
C6 C11 H11 119.2
C10 C11 C6 121.5(3)
C10 C11 H11 119.2
C7 C12 H12A 109.5
C7 C12 H12B 109.5
C7 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7307(16)
S1 C3 1.7202(18)
O1 C4 1.222(2)
N1 H1 0.8800
N1 C1 1.378(2)
N1 C4 1.361(2)
N2 C1 1.307(2)
N2 C2 1.382(2)
C2 H2 0.9500
C2 C3 1.349(2)
C3 H3 0.9500
C4 C5 1.521(2)
C5 H5A 0.9900
C5 H5B 0.9900
C5 C6 1.506(2)
C6 C7 1.386(3)
C6 C11 1.394(3)
C7 C8 1.399(3)
C7 C12 1.502(4)
C8 H8 0.9500
C8 C9 1.365(5)
C9 H9 0.9500
C9 C10 1.375(5)
C10 H10 0.9500
C10 C11 1.375(4)
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 N2 3_666 0.88 2.04 2.9138(19) 176
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
O1 C4 C5 C6 9.8(3)
N1 C4 C5 C6 -170.71(15)
N2 C2 C3 S1 0.6(2)
C1 S1 C3 C2 0.12(13)
C1 N1 C4 O1 1.8(3)
C1 N1 C4 C5 -177.74(14)
C1 N2 C2 C3 -1.3(2)
C2 N2 C1 S1 1.36(17)
C2 N2 C1 N1 -179.21(14)
C3 S1 C1 N1 179.70(14)
C3 S1 C1 N2 -0.89(13)
C4 N1 C1 S1 -4.9(2)
C4 N1 C1 N2 175.74(14)
C4 C5 C6 C7 -86.3(2)
C4 C5 C6 C11 92.8(2)
C5 C6 C7 C8 178.75(19)
C5 C6 C7 C12 -2.2(3)
C5 C6 C11 C10 -177.9(2)
C6 C7 C8 C9 -0.7(4)
C7 C6 C11 C10 1.1(4)
C7 C8 C9 C10 0.8(5)
C8 C9 C10 C11 0.0(5)
C9 C10 C11 C6 -1.0(5)
C11 C6 C7 C8 -0.3(3)
C11 C6 C7 C12 178.7(2)
C12 C7 C8 C9 -179.7(3)
