##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2008-05-12
_journal_date_accepted     2008-05-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o1084
_journal_page_last     o1084
_journal_paper_category     QO
_journal_coeditor_code     HB2733
_publ_contact_author_name
;
Mehmet Akkurt
;
_publ_contact_author_address
; Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
_publ_contact_author_email     'akkurt@erciyes.edu.tr'
_publ_contact_author_fax     '+90-352-4374933'
_publ_contact_author_phone     '+90-352-4374901 extra 33106'
_publ_section_title
;
Ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Mehmet Akkurt'
; Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
    'Sema Öztürk Yıldırım'
; Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
    'Abdullah Mohamed Asiri'
;
Chemistry Department
Faculty of Science
King Abdul-Aziz University
PO Box 80203
Jeddah 21589
Saudi Arabia
;
    'Vickie McKee'
;
   Department of Chemistry
   Loughborough University
   Leicestershire LE11 3TU
   England
;
data_I
_chemical_name_systematic
;
Ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H13 N O3 S'
_chemical_formula_sum     'C10 H13 N O3 S'
_chemical_formula_iupac     'C10 H13 N O3 S'
_chemical_formula_weight     227.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2+y,1/2-z
    3 -x,-y,-z
    4 1/2+x,1/2-y,1/2+z
_cell_length_a     7.5397(3)
_cell_length_b     8.4514(3)
_cell_length_c     16.7058(6)
_cell_angle_alpha     90
_cell_angle_beta     94.4650(10)
_cell_angle_gamma     90
_cell_volume     1061.28(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4913
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     31.07
_cell_measurement_temperature     150(2)
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.10
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.423
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.291
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.920
_exptl_absorpt_correction_T_max     0.971
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12338
_diffrn_reflns_av_R_equivalents     0.0246
_diffrn_reflns_av_sigmaI/netI     0.0228
_diffrn_reflns_theta_min     2.45
_diffrn_reflns_theta_max     31.84
_diffrn_reflns_theta_full     31.84
_diffrn_measured_fraction_theta_max     0.934
_diffrn_measured_fraction_theta_full     0.934
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     24
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger.
;
_reflns_number_total     3400
_reflns_number_gt     2944
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0447
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.1052
_refine_ls_wR_factor_ref     0.1107
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.049
_refine_ls_number_reflns     3400
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.06P)²+0.3751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.443
_refine_diff_density_min     -0.339
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    S S 0.1246 0.1234 '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'
    N N 0.0061 0.0033 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'APEX2 (Bruker, 2005)'
_computing_data_reduction     'APEX2 (Bruker, 2005)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    S S1 0.74240(4) 0.44716(4) 0.82882(2) 0.02340(10)
                                                    Uani . . 1.000
    O O1 0.58575(14) 0.74136(13) 0.79734(6) 0.0324(3) Uani . . 1.000
    O O2 0.94110(15) 0.13922(12) 1.03979(6) 0.0315(3) Uani . . 1.000
    O O3 0.83808(13) 0.32842(11) 1.11776(5) 0.0251(3) Uani . . 1.000
    N N1 0.88307(16) 0.17090(13) 0.87660(6) 0.0263(3) Uani . . 1.000
    C C1 0.5682(2) 0.86338(17) 0.92406(8) 0.0307(4) Uani . . 1.000
    C C2 0.61541(17) 0.72854(15) 0.87090(7) 0.0240(3) Uani . . 1.000
    C C3 0.69568(16) 0.58332(15) 0.90307(7) 0.0210(3) Uani . . 1.000
    C C4 0.74019(15) 0.52653(14) 0.97964(7) 0.0191(3) Uani . . 1.000
    C C5 0.71928(18) 0.61996(15) 1.05495(7) 0.0249(3) Uani . . 1.000
    C C6 0.81050(15) 0.36847(14) 0.97838(7) 0.0194(3) Uani . . 1.000
    C C7 0.82188(16) 0.31123(14) 0.89967(7) 0.0208(3) Uani . . 1.000
    C C8 0.87045(16) 0.26784(14) 1.04635(7) 0.0207(3) Uani . . 1.000
    C C9 0.90152(19) 0.23865(16) 1.18821(7) 0.0272(3) Uani . . 1.000
    C C10 0.8610(2) 0.33700(19) 1.25956(8) 0.0325(4) Uani . . 1.000
    H HN1A 0.92190 0.10290 0.91200 0.0320 Uiso calc R 1.000
    H H1A 0.51730 0.94800 0.89160 0.0460 Uiso calc . 0.500
    H H1B 0.67360 0.90040 0.95430 0.0460 Uiso calc . 0.500
    H H1C 0.48370 0.82780 0.96020 0.0460 Uiso calc . 0.500
    H H1D 0.59910 0.83610 0.97920 0.0460 Uiso calc . 0.500
    H H1E 0.44280 0.88380 0.91640 0.0460 Uiso calc . 0.500
    H H1F 0.63260 0.95630 0.91050 0.0460 Uiso calc . 0.500
    H HN1B 0.88350 0.14890 0.82640 0.0320 Uiso calc R 1.000
    H H5A 0.75800 0.55710 1.10090 0.0370 Uiso calc . 0.500
    H H5B 0.59650 0.64800 1.05770 0.0370 Uiso calc . 0.500
    H H5C 0.78990 0.71440 1.05430 0.0370 Uiso calc . 0.500
    H H5D 0.67160 0.72250 1.04100 0.0370 Uiso calc . 0.500
    H H5E 0.83320 0.63170 1.08430 0.0370 Uiso calc . 0.500
    H H5F 0.63970 0.56530 1.08760 0.0370 Uiso calc . 0.500
    H H9A 1.02850 0.21990 1.18830 0.0330 Uiso calc R 1.000
    H H9B 0.84120 0.13740 1.18920 0.0330 Uiso calc R 1.000
    H H10A 0.90050 0.28220 1.30800 0.0490 Uiso calc R 1.000
    H H10B 0.73510 0.35490 1.25850 0.0490 Uiso calc R 1.000
    H H10C 0.92150 0.43670 1.25770 0.0490 Uiso calc R 1.000
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 0.0306(2) 0.0254(2) 0.01420(10)
                                     -0.00320(10)
                                                0.00170(10)
                                                          -0.00090(10)
    O1 0.0409(6) 0.0366(5) 0.0198(4) 0.0027(4) 0.0031(4) 0.0076(4)
    O2 0.0468(6) 0.0238(4) 0.0241(5) 0.0083(4) 0.0037(4) -0.0003(3)
    O3 0.0348(5) 0.0258(4) 0.0147(4) 0.0055(4) 0.0015(3) 0.0012(3)
    N1 0.0373(6) 0.0222(5) 0.0197(5) -0.0009(4) 0.0038(4) -0.0052(4)
    C1 0.0386(7) 0.0263(6) 0.0271(6) 0.0064(5) 0.0016(5) 0.0038(5)
    C2 0.0248(5) 0.0262(6) 0.0212(5) -0.0031(4) 0.0027(4) 0.0040(4)
    C3 0.0245(5) 0.0224(5) 0.0163(5) -0.0032(4) 0.0023(4) -0.0006(4)
    C4 0.0200(5) 0.0211(5) 0.0164(5) -0.0030(4) 0.0022(4) -0.0010(4)
    C5 0.0327(6) 0.0246(6) 0.0174(5) 0.0024(5) 0.0017(4) -0.0026(4)
    C6 0.0216(5) 0.0206(5) 0.0161(5) -0.0026(4) 0.0018(4) -0.0013(4)
    C7 0.0228(5) 0.0217(5) 0.0180(5) -0.0045(4) 0.0024(4) -0.0017(4)
    C8 0.0234(5) 0.0215(5) 0.0173(5) -0.0025(4) 0.0019(4) -0.0008(4)
    C9 0.0360(7) 0.0270(6) 0.0185(5) 0.0027(5) 0.0010(5) 0.0057(4)
    C10 0.0407(7) 0.0392(7) 0.0179(5) 0.0024(6) 0.0044(5) 0.0023(5)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C3 . . 1.7479(13) no
    S1 C7 . . 1.7232(12) no
    O1 C2 . . 1.2366(15) no
    O2 C8 . . 1.2192(16) no
    O3 C8 . . 1.3380(15) no
    O3 C9 . . 1.4498(15) no
    N1 C7 . . 1.3400(16) no
    N1 HN1A . . 0.8600 no
    N1 HN1B . . 0.8600 no
    C1 C2 . . 1.5044(19) no
    C2 C3 . . 1.4529(18) no
    C3 C4 . . 1.3829(17) no
    C4 C6 . . 1.4379(17) no
    C4 C5 . . 1.5040(17) no
    C6 C7 . . 1.4100(17) no
    C6 C8 . . 1.4619(17) no
    C9 C10 . . 1.5039(19) no
    C1 H1A . . 0.9600 no
    C1 H1B . . 0.9600 no
    C1 H1C . . 0.9600 no
    C1 H1D . . 0.9600 no
    C1 H1E . . 0.9600 no
    C1 H1F . . 0.9600 no
    C5 H5A . . 0.9600 no
    C5 H5B . . 0.9600 no
    C5 H5C . . 0.9600 no
    C5 H5D . . 0.9600 no
    C5 H5E . . 0.9600 no
    C5 H5F . . 0.9600 no
    C9 H9A . . 0.9700 no
    C9 H9B . . 0.9700 no
    C10 H10A . . 0.9600 no
    C10 H10B . . 0.9600 no
    C10 H10C . . 0.9600 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 S1 C7 . . . 91.72(6) no
    C8 O3 C9 . . . 116.87(10) no
    HN1A N1 HN1B . . . 120.00 no
    C7 N1 HN1A . . . 120.00 no
    C7 N1 HN1B . . . 120.00 no
    O1 C2 C1 . . . 119.18(12) no
    O1 C2 C3 . . . 118.66(11) no
    C1 C2 C3 . . . 122.17(11) no
    S1 C3 C2 . . . 113.26(9) no
    C2 C3 C4 . . . 134.38(11) no
    S1 C3 C4 . . . 112.34(9) no
    C5 C4 C6 . . . 124.25(10) no
    C3 C4 C6 . . . 111.84(10) no
    C3 C4 C5 . . . 123.91(11) no
    C4 C6 C7 . . . 112.44(10) no
    C4 C6 C8 . . . 128.40(11) no
    C7 C6 C8 . . . 119.16(10) no
    N1 C7 C6 . . . 128.26(11) no
    S1 C7 N1 . . . 120.11(9) no
    S1 C7 C6 . . . 111.64(9) no
    O2 C8 O3 . . . 122.18(11) no
    O2 C8 C6 . . . 124.04(11) no
    O3 C8 C6 . . . 113.77(10) no
    O3 C9 C10 . . . 106.24(11) no
    C2 C1 H1A . . . 109.00 no
    C2 C1 H1B . . . 109.00 no
    C2 C1 H1C . . . 109.00 no
    C2 C1 H1D . . . 109.00 no
    C2 C1 H1E . . . 109.00 no
    C2 C1 H1F . . . 109.00 no
    H1A C1 H1B . . . 109.00 no
    H1A C1 H1C . . . 109.00 no
    H1A C1 H1D . . . 141.00 no
    H1A C1 H1E . . . 56.00 no
    H1A C1 H1F . . . 56.00 no
    H1B C1 H1C . . . 110.00 no
    H1B C1 H1D . . . 56.00 no
    H1B C1 H1E . . . 141.00 no
    H1B C1 H1F . . . 56.00 no
    H1C C1 H1D . . . 56.00 no
    H1C C1 H1E . . . 56.00 no
    H1C C1 H1F . . . 141.00 no
    H1D C1 H1E . . . 110.00 no
    H1D C1 H1F . . . 109.00 no
    H1E C1 H1F . . . 109.00 no
    C4 C5 H5A . . . 109.00 no
    C4 C5 H5B . . . 110.00 no
    C4 C5 H5C . . . 109.00 no
    C4 C5 H5D . . . 109.00 no
    C4 C5 H5E . . . 109.00 no
    C4 C5 H5F . . . 109.00 no
    H5A C5 H5B . . . 109.00 no
    H5A C5 H5C . . . 110.00 no
    H5A C5 H5D . . . 141.00 no
    H5A C5 H5E . . . 56.00 no
    H5A C5 H5F . . . 56.00 no
    H5B C5 H5C . . . 109.00 no
    H5B C5 H5D . . . 56.00 no
    H5B C5 H5E . . . 141.00 no
    H5B C5 H5F . . . 56.00 no
    H5C C5 H5D . . . 56.00 no
    H5C C5 H5E . . . 56.00 no
    H5C C5 H5F . . . 141.00 no
    H5D C5 H5E . . . 109.00 no
    H5D C5 H5F . . . 109.00 no
    H5E C5 H5F . . . 109.00 no
    O3 C9 H9A . . . 110.00 no
    O3 C9 H9B . . . 110.00 no
    C10 C9 H9A . . . 111.00 no
    C10 C9 H9B . . . 110.00 no
    H9A C9 H9B . . . 109.00 no
    C9 C10 H10A . . . 109.00 no
    C9 C10 H10B . . . 110.00 no
    C9 C10 H10C . . . 109.00 no
    H10A C10 H10B . . . 109.00 no
    H10A C10 H10C . . . 110.00 no
    H10B C10 H10C . . . 109.00 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 S1 C3 C2 . . . . -178.44(10) no
    C7 S1 C3 C4 . . . . 0.21(10) no
    C3 S1 C7 N1 . . . . -179.68(11) no
    C3 S1 C7 C6 . . . . 0.76(10) no
    C9 O3 C8 O2 . . . . 3.93(18) no
    C9 O3 C8 C6 . . . . -177.14(10) no
    C8 O3 C9 C10 . . . . 175.85(11) no
    O1 C2 C3 S1 . . . . 1.18(16) no
    O1 C2 C3 C4 . . . . -177.07(13) no
    C1 C2 C3 S1 . . . . -178.56(10) no
    C1 C2 C3 C4 . . . . 3.2(2) no
    S1 C3 C4 C5 . . . . 178.25(10) no
    S1 C3 C4 C6 . . . . -1.10(13) no
    C2 C3 C4 C5 . . . . -3.5(2) no
    C2 C3 C4 C6 . . . . 177.16(13) no
    C3 C4 C6 C7 . . . . 1.69(15) no
    C3 C4 C6 C8 . . . . -179.30(12) no
    C5 C4 C6 C7 . . . . -177.67(11) no
    C5 C4 C6 C8 . . . . 1.35(19) no
    C4 C6 C7 S1 . . . . -1.52(13) no
    C4 C6 C7 N1 . . . . 178.96(12) no
    C8 C6 C7 S1 . . . . 179.36(9) no
    C8 C6 C7 N1 . . . . -0.2(2) no
    C4 C6 C8 O2 . . . . -174.17(12) no
    C4 C6 C8 O3 . . . . 6.93(18) no
    C7 C6 C8 O2 . . . . 4.79(19) no
    C7 C6 C8 O3 . . . . -174.12(11) no
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
    _geom_hbond_publ_flag
    N1 HN1A O2 . 0.86 2.15 2.7404(14) 125 yes
    N1 HN1A O2 3_757 0.86 2.40 3.2077(15) 156 yes
    N1 HN1B O1 2_646 0.86 2.24 2.9933(14) 147 yes
    C5 H5A O3 . 0.96 2.04 2.7978(16) 135 yes
