##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-[4-Acetyl-5-methyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-
thiadiazol-2-yl]acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H23 N3 O2 S'
_chemical_formula_sum     'C17 H23 N3 O2 S'
_chemical_formula_iupac     'C17 H23 N3 O2 S'
_chemical_formula_weight     333.44
_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_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.3984(2)
_cell_length_b     11.0510(2)
_cell_length_c     16.6045(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.442(10)
_cell_angle_gamma     90.00
_cell_volume     1724.52(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     31976
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     36.46
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.3
_exptl_crystal_density_diffrn     1.284
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     712
_exptl_absorpt_coefficient_mu     0.201
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     52162
_diffrn_reflns_av_R_equivalents     0.0189
_diffrn_reflns_av_sigmaI/netI     0.0118
_diffrn_reflns_theta_min     2.21
_diffrn_reflns_theta_max     36.75
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     8286
_reflns_number_gt     7182
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0410
_refine_ls_R_factor_gt     0.0345
_refine_ls_wR_factor_gt     0.1016
_refine_ls_wR_factor_ref     0.1077
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     8286
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0594P)²+0.2773P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.507
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    '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'
_computing_data_collection     'APEX-W2K-NT (Bruker, 2005)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2005)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                               'ORTEP-3 (Farrugia,1997) and PLATON (Spek, 2003)'
_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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1' -0.18648(9) 0.69929(8) 0.22865(5) 0.03405(16) Uani d . 1 . .
    H H1' -0.2631 0.7423 0.2493 0.041 Uiso calc R 1 . .
    C C2' -0.12028(8) 0.74007(7) 0.15872(5) 0.02883(13) Uani d . 1 . .
    H H2' -0.1553 0.8087 0.1329 0.035 Uiso calc R 1 . .
    C C2 0.40705(7) 0.72005(6) 0.13520(4) 0.02074(10) Uani d . 1 . .
    C C3' -0.00246(7) 0.68003(6) 0.12659(4) 0.02299(11) Uani d . 1 . .
    C C3 0.58917(7) 0.58558(7) 0.08145(4) 0.02531(12) Uani d . 1 . .
    C C4 0.67040(8) 0.47195(8) 0.09881(5) 0.03082(14) Uani d . 1 . .
    H H40 0.6397 0.4094 0.0625 0.046 Uiso calc R 1 . .
    H H41 0.6534 0.4471 0.1533 0.046 Uiso calc R 1 . .
    H H42 0.7702 0.4865 0.0917 0.046 Uiso calc R 1 . .
    C C4' 0.04426(8) 0.57608(7) 0.16569(5) 0.02818(13) Uani d . 1 . .
    H H4' 0.1221 0.5340 0.1458 0.034 Uiso calc R 1 . .
    C C5 0.24444(7) 0.89236(6) 0.09425(4) 0.02261(11) Uani d . 1 . .
    C C5' -0.02462(10) 0.53384(8) 0.23496(5) 0.03469(17) Uani d . 1 . .
    H H5' 0.0073 0.4631 0.2595 0.042 Uiso calc R 1 . .
    C C6 0.10835(8) 0.85717(6) 0.04946(4) 0.02444(12) Uani d . 1 . .
    H H61 0.1172 0.8834 -0.0060 0.029 Uiso calc R 1 . .
    H H62 0.0302 0.9021 0.0728 0.029 Uiso calc R 1 . .
    C C6' -0.13955(10) 0.59549(9) 0.26777(5) 0.03553(17) Uani d . 1 . .
    C C7' -0.21196(14) 0.55330(13) 0.34392(6) 0.0557(3) Uani d . 1 . .
    H H70' -0.1661 0.4813 0.3634 0.083 Uiso calc R 1 . .
    H H71' -0.3103 0.5363 0.3325 0.083 Uiso calc R 1 . .
    H H72' -0.2054 0.6155 0.3841 0.083 Uiso calc R 1 . .
    C C7 0.06784(7) 0.72237(6) 0.04914(4) 0.02407(11) Uani d . 1 . .
    C C8 -0.02971(10) 0.69513(9) -0.02232(5) 0.03593(17) Uani d . 1 . .
    H H80 0.0164 0.7187 -0.0713 0.054 Uiso calc R 1 . .
    H H81 -0.1169 0.7395 -0.0168 0.054 Uiso calc R 1 . .
    H H82 -0.0501 0.6100 -0.0239 0.054 Uiso calc R 1 . .
    C C9 0.27064(10) 1.02844(7) 0.08864(5) 0.03188(15) Uani d . 1 . .
    H H90 0.3533 1.0493 0.1200 0.048 Uiso calc R 1 . .
    H H91 0.1895 1.0711 0.1090 0.048 Uiso calc R 1 . .
    H H92 0.2855 1.0505 0.0334 0.048 Uiso calc R 1 . .
    C C41 0.15568(7) 0.88983(6) 0.23768(4) 0.02220(11) Uani d . 1 . .
    C C42 0.16402(9) 0.82781(7) 0.31792(4) 0.02797(13) Uani d . 1 . .
    H H420 0.1094 0.7544 0.3161 0.042 Uiso calc R 1 . .
    H H421 0.1265 0.8802 0.3587 0.042 Uiso calc R 1 . .
    H H422 0.2615 0.8091 0.3304 0.042 Uiso calc R 1 . .
    N N1 0.49426(6) 0.61997(5) 0.14026(3) 0.02274(10) Uani d . 1 . .
    N N3 0.32596(6) 0.74595(5) 0.19539(3) 0.02162(10) Uani d . 1 . .
    N N4 0.24397(6) 0.84788(5) 0.17882(3) 0.02167(10) Uani d . 1 . .
    O O1 0.60479(7) 0.64374(7) 0.01970(4) 0.03731(14) Uani d . 1 . .
    O O2 0.07229(6) 0.97409(5) 0.22442(3) 0.02734(10) Uani d . 1 . .
    S S1 0.400452(18) 0.813333(16) 0.050251(10) 0.02473(5) Uani d . 1 . .
    H H4 0.4838(13) 0.5774(12) 0.1853(8) 0.036(3) Uiso d . 1 . .
    H H7 0.1540(12) 0.6750(10) 0.0411(7) 0.028(3) Uiso d . 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1' C6' . 1.3886(14) ?
    C1' C2' . 1.3963(12) ?
    C1' H1' . 0.93 ?
    C2' C3' . 1.4001(10) ?
    C2' H2' . 0.93 ?
    C2 N3 . 1.2936(8) ?
    C2 N1 . 1.3788(9) ?
    C2 S1 . 1.7478(6) ?
    C3' C4' . 1.3891(10) ?
    C3' C7 . 1.5239(10) ?
    C3 O1 . 1.2199(9) ?
    C3 N1 . 1.3810(9) ?
    C3 C4 . 1.4966(11) ?
    C4 H40 . 0.96 ?
    C4 H41 . 0.96 ?
    C4 H42 . 0.96 ?
    C4' C5' . 1.4040(12) ?
    C4' H4' . 0.93 ?
    C5 N4 . 1.4878(8) ?
    C5 C6 . 1.5250(10) ?
    C5 C9 . 1.5267(10) ?
    C5 S1 . 1.8609(7) ?
    C5' C6' . 1.3916(14) ?
    C5' H5' . 0.93 ?
    C6 C7 . 1.5375(10) ?
    C6 H61 . 0.97 ?
    C6 H62 . 0.97 ?
    C6' C7' . 1.5142(13) ?
    C7' H70' . 0.96 ?
    C7' H71' . 0.96 ?
    C7' H72' . 0.96 ?
    C7 C8 . 1.5240(10) ?
    C7 H7 . 0.974(11) ?
    C8 H80 . 0.96 ?
    C8 H81 . 0.96 ?
    C8 H82 . 0.96 ?
    C9 H90 . 0.96 ?
    C9 H91 . 0.96 ?
    C9 H92 . 0.96 ?
    C41 O2 . 1.2357(8) ?
    C41 N4 . 1.3679(8) ?
    C41 C42 . 1.4998(10) ?
    C42 H420 . 0.96 ?
    C42 H421 . 0.96 ?
    C42 H422 . 0.96 ?
    N1 H4 . 0.889(13) ?
    N3 N4 . 1.3911(8) ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    C6' C1' C2' . . 120.90(8) ?
    C6' C1' H1' . . 119.5 ?
    C2' C1' H1' . . 119.5 ?
    C1' C2' C3' . . 121.52(7) ?
    C1' C2' H2' . . 119.2 ?
    C3' C2' H2' . . 119.2 ?
    N3 C2 N1 . . 118.94(6) ?
    N3 C2 S1 . . 118.40(5) ?
    N1 C2 S1 . . 122.66(5) ?
    C4' C3' C2' . . 117.51(7) ?
    C4' C3' C7 . . 120.72(6) ?
    C2' C3' C7 . . 121.70(6) ?
    O1 C3 N1 . . 122.14(7) ?
    O1 C3 C4 . . 122.65(7) ?
    N1 C3 C4 . . 115.21(6) ?
    C3 C4 H40 . . 109.5 ?
    C3 C4 H41 . . 109.5 ?
    H40 C4 H41 . . 109.5 ?
    C3 C4 H42 . . 109.5 ?
    H40 C4 H42 . . 109.5 ?
    H41 C4 H42 . . 109.5 ?
    C3' C4' C5' . . 120.78(8) ?
    C3' C4' H4' . . 119.6 ?
    C5' C4' H4' . . 119.6 ?
    N4 C5 C6 . . 111.56(5) ?
    N4 C5 C9 . . 112.62(6) ?
    C6 C5 C9 . . 110.89(6) ?
    N4 C5 S1 . . 102.92(4) ?
    C6 C5 S1 . . 110.44(5) ?
    C9 C5 S1 . . 108.08(5) ?
    C6' C5' C4' . . 121.47(8) ?
    C6' C5' H5' . . 119.3 ?
    C4' C5' H5' . . 119.3 ?
    C5 C6 C7 . . 117.10(5) ?
    C5 C6 H61 . . 108.0 ?
    C7 C6 H61 . . 108.0 ?
    C5 C6 H62 . . 108.0 ?
    C7 C6 H62 . . 108.0 ?
    H61 C6 H62 . . 107.3 ?
    C1' C6' C5' . . 117.78(7) ?
    C1' C6' C7' . . 120.12(10) ?
    C5' C6' C7' . . 122.10(10) ?
    C6' C7' H70' . . 109.5 ?
    C6' C7' H71' . . 109.5 ?
    H70' C7' H71' . . 109.5 ?
    C6' C7' H72' . . 109.5 ?
    H70' C7' H72' . . 109.5 ?
    H71' C7' H72' . . 109.5 ?
    C3' C7 C8 . . 109.53(6) ?
    C3' C7 C6 . . 113.80(5) ?
    C8 C7 C6 . . 109.97(6) ?
    C3' C7 H7 . . 108.5(7) ?
    C8 C7 H7 . . 106.4(7) ?
    C6 C7 H7 . . 108.3(7) ?
    C7 C8 H80 . . 109.5 ?
    C7 C8 H81 . . 109.5 ?
    H80 C8 H81 . . 109.5 ?
    C7 C8 H82 . . 109.5 ?
    H80 C8 H82 . . 109.5 ?
    H81 C8 H82 . . 109.5 ?
    C5 C9 H90 . . 109.5 ?
    C5 C9 H91 . . 109.5 ?
    H90 C9 H91 . . 109.5 ?
    C5 C9 H92 . . 109.5 ?
    H90 C9 H92 . . 109.5 ?
    H91 C9 H92 . . 109.5 ?
    O2 C41 N4 . . 121.03(6) ?
    O2 C41 C42 . . 122.10(6) ?
    N4 C41 C42 . . 116.87(6) ?
    C41 C42 H420 . . 109.5 ?
    C41 C42 H421 . . 109.5 ?
    H420 C42 H421 . . 109.5 ?
    C41 C42 H422 . . 109.5 ?
    H420 C42 H422 . . 109.5 ?
    H421 C42 H422 . . 109.5 ?
    C2 N1 C3 . . 124.37(6) ?
    C2 N1 H4 . . 113.9(8) ?
    C3 N1 H4 . . 121.7(8) ?
    C2 N3 N4 . . 110.79(5) ?
    C41 N4 N3 . . 118.12(5) ?
    C41 N4 C5 . . 124.65(5) ?
    N3 N4 C5 . . 116.65(5) ?
    C2 S1 C5 . . 89.03(3) ?
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 H4 O2 2_545 0.890(10)
                           1.960(10)
                                   2.8391(7) 169.0(10)
                                                    yes
data_global
_journal_date_recd_electronic     2008-12-16
_journal_date_accepted     2009-01-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     o267
_journal_page_last     o268
_journal_paper_category     QO
_journal_coeditor_code     CI2746
_publ_contact_author_name     'Professor Moha Berraho'
_publ_contact_author_address
;
Laboratoire de Chimie Biomoléculaires, Substances Naturelles
et réactivité Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
;
_publ_contact_author_email     mberraho@yahoo.fr
_publ_contact_author_fax     '0021224437408'
_publ_contact_author_phone     '0021224434649'
_publ_section_title
;\
N-[4-Acetyl-5-methyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-\
thiadiazol-2-yl]acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Tebaa, Mohamed'
;
Laboratoire de Chimie Biomoléculaires
Substances Naturelles et Réactivité
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
;
    'Mazoir, Noureddine'
;
Laboratoire de Chimie Biomoléculaires
Substances Naturelles et Réactivité
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
;
    'Maya, Celia M.'
;
Instituto de Química Física Rocasolano
Consejo Superior de Investigaciones Científicas
Serrano, 119 28002 Madrid
Spain
;
    'Bouhmaida Nouzha'
;
Laboratoire des Sciences des Matériaux
Département de Physique
Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah,
40000 Marrakech, Morocco
;
    'Benharref, Ahmed'
;
Laboratoire de Chimie Biomoléculaires,
Substances Naturelles et Réactivité
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
;
    'Berraho, Moha'
;
Laboratoire de Chimie Biomoléculaires
Substances Naturelles et Réactivité
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
;
