#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/72/2237239.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_2237239
loop_
_publ_author_name
'You, Xin-Yu'
'Shi, Yao-Jie'
'Yu, Luo-Ting'
_publ_section_title
;
 (E)-3-Dimethylamino-1-(1,3-thiazol-2-yl)prop-2-en-1-one
;
_journal_coeditor_code           VM2183
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o18
_journal_paper_doi               10.1107/S1600536812048817
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H10 N2 O S'
_chemical_formula_moiety         'C8 H10 N2 O S'
_chemical_formula_sum            'C8 H10 N2 O S'
_chemical_formula_weight         182.24
_chemical_name_systematic
;
(E)-3-Dimethylamino-1-(1,3-thiazol-2-yl)prop-2-en-1-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.498(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6252(2)
_cell_length_b                   22.5957(8)
_cell_length_c                   7.5777(3)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      28.8180
_cell_measurement_theta_min      2.9848
_cell_volume                     907.93(6)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      135.00(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3683
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.2132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                1565
_reflns_number_total             1846
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2183.cif
_cod_data_source_block           I
_cod_database_code               2237239
_cod_database_fobs_code          2237239
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -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
_atom_site_symmetry_multiplicity
S S1 0.48299(8) 0.15794(2) 0.44117(6) 0.02965(16) Uani d . 1 1
O O1 0.5387(2) 0.06419(5) 0.19443(16) 0.0293(3) Uani d . 1 1
N N1 0.8366(2) 0.20354(6) 0.34119(19) 0.0269(3) Uani d . 1 1
N N2 0.9036(2) 0.06400(6) -0.19641(18) 0.0243(3) Uani d . 1 1
C C1 0.6877(3) 0.15752(7) 0.3145(2) 0.0214(4) Uani d . 1 1
C C2 0.6091(3) 0.22388(9) 0.5379(2) 0.0347(4) Uani d . 1 1
H H2 0.5586 0.2455 0.6269 0.042 Uiso calc R 1 1
C C3 0.7920(3) 0.24077(8) 0.4690(2) 0.0336(4) Uani d . 1 1
H H3 0.8841 0.2765 0.5073 0.040 Uiso calc R 1 1
C C4 0.6732(3) 0.10684(7) 0.1844(2) 0.0215(4) Uani d . 1 1
C C5 0.8103(3) 0.11210(7) 0.0581(2) 0.0226(4) Uani d . 1 1
H H5 0.9141 0.1456 0.0619 0.027 Uiso calc R 1 1
C C6 0.7890(3) 0.06752(7) -0.0696(2) 0.0221(4) Uani d . 1 1
H H6 0.6800 0.0357 -0.0667 0.026 Uiso calc R 1 1
C C8 0.8565(3) 0.01509(8) -0.3283(2) 0.0308(4) Uani d . 1 1
H H8A 0.7469 -0.0140 -0.2980 0.046 Uiso calc R 1 1
H H8B 1.0169 -0.0037 -0.3203 0.046 Uiso calc R 1 1
H H8C 0.7740 0.0300 -0.4556 0.046 Uiso calc R 1 1
C C9 1.0815(3) 0.10914(9) -0.2102(2) 0.0342(4) Uani d . 1 1
H H9A 1.0028 0.1482 -0.2203 0.051 Uiso calc R 1 1
H H9B 1.1291 0.1017 -0.3214 0.051 Uiso calc R 1 1
H H9C 1.2324 0.1078 -0.0982 0.051 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0328(3) 0.0320(3) 0.0283(3) 0.00526(19) 0.0159(2) -0.00177(19)
O1 0.0389(7) 0.0259(7) 0.0287(6) -0.0064(6) 0.0186(5) -0.0032(5)
N1 0.0274(7) 0.0248(8) 0.0253(7) 0.0021(6) 0.0046(6) -0.0015(6)
N2 0.0267(7) 0.0290(8) 0.0204(7) 0.0021(6) 0.0121(6) 0.0029(6)
C1 0.0214(8) 0.0238(9) 0.0178(8) 0.0062(7) 0.0050(6) 0.0029(7)
C2 0.0428(10) 0.0309(10) 0.0292(9) 0.0115(9) 0.0102(8) -0.0059(8)
C3 0.0378(10) 0.0255(10) 0.0318(9) 0.0040(8) 0.0040(8) -0.0064(8)
C4 0.0232(8) 0.0223(8) 0.0179(8) 0.0028(7) 0.0052(6) 0.0026(7)
C5 0.0238(8) 0.0235(9) 0.0209(8) -0.0005(7) 0.0079(7) 0.0018(7)
C6 0.0225(8) 0.0253(9) 0.0190(8) 0.0021(7) 0.0077(6) 0.0055(7)
C8 0.0439(10) 0.0298(10) 0.0247(9) 0.0073(8) 0.0193(8) 0.0019(8)
C9 0.0297(9) 0.0466(12) 0.0299(9) -0.0064(9) 0.0148(8) 0.0032(9)
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
C2 S1 C1 89.13(9)
C1 N1 C3 109.85(14)
C6 N2 C8 121.51(14)
C6 N2 C9 121.45(15)
C8 N2 C9 117.04(13)
N1 C1 S1 114.87(12)
N1 C1 C4 127.05(14)
C4 C1 S1 118.07(12)
S1 C2 H2 125.0
C3 C2 S1 109.92(14)
C3 C2 H2 125.0
N1 C3 H3 121.9
C2 C3 N1 116.23(17)
C2 C3 H3 121.9
O1 C4 C1 116.99(14)
O1 C4 C5 125.77(15)
C5 C4 C1 117.22(14)
C4 C5 H5 120.9
C6 C5 C4 118.28(15)
C6 C5 H5 120.9
N2 C6 C5 127.23(16)
N2 C6 H6 116.4
C5 C6 H6 116.4
N2 C8 H8A 109.5
N2 C8 H8B 109.5
N2 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C9 H9A 109.5
N2 C9 H9B 109.5
N2 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7282(16)
S1 C2 1.707(2)
O1 C4 1.2432(19)
N1 C1 1.308(2)
N1 C3 1.368(2)
N2 C6 1.3264(19)
N2 C8 1.454(2)
N2 C9 1.457(2)
C1 C4 1.495(2)
C2 H2 0.9500
C2 C3 1.355(3)
C3 H3 0.9500
C4 C5 1.420(2)
C5 H5 0.9500
C5 C6 1.374(2)
C6 H6 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 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
C2 H2 N1 4_566 0.95 2.62 3.560(2) 169.3
C6 H6 O1 3_655 0.95 2.60 3.462(2) 151.4
C8 H8A O1 3_655 0.98 2.31 3.269(2) 166.8
C9 H9C O1 1_655 0.98 2.51 3.433(2) 156.5
C9 H9A Cg1 1_554 0.98 2.93 3.549(2) 122.0
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
S1 C1 C4 O1 -9.54(19)
S1 C1 C4 C5 169.33(11)
S1 C2 C3 N1 0.2(2)
O1 C4 C5 C6 2.2(2)
N1 C1 C4 O1 172.31(15)
N1 C1 C4 C5 -8.8(2)
C1 S1 C2 C3 0.25(14)
C1 N1 C3 C2 -0.7(2)
C1 C4 C5 C6 -176.53(13)
C2 S1 C1 N1 -0.70(13)
C2 S1 C1 C4 -179.08(13)
C3 N1 C1 S1 0.92(17)
C3 N1 C1 C4 179.13(15)
C4 C5 C6 N2 -179.08(15)
C8 N2 C6 C5 -177.66(15)
C9 N2 C6 C5 2.1(3)
