#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220735.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_2220735
loop_
_publ_author_name
'Tebaa, Mohamed'
'Mazoir, Noureddine'
'Maya, Celia M.'
'Nouzha, Bouhmaida'
'Benharref, Ahmed'
'Berraho, Moha'
_publ_section_title
N-[4-Acetyl-5-methyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide
_journal_coeditor_code           CI2746
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o267
_journal_page_last               o268
_journal_paper_doi               10.1107/S1600536809000191
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H23 N3 O2 S'
_chemical_formula_moiety         'C17 H23 N3 O2 S'
_chemical_formula_sum            'C17 H23 N3 O2 S'
_chemical_formula_weight         333.44
_chemical_name_systematic
;
N-[4-Acetyl-5-methyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-
thiadiazol-2-yl]acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.442(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3984(2)
_cell_length_b                   11.0510(2)
_cell_length_c                   16.6045(3)
_cell_measurement_reflns_used    31976
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      36.46
_cell_measurement_theta_min      2.21
_cell_volume                     1724.52(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2005)'
_computing_data_collection       'APEX-W2K-NT (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia,1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker X8 APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            52162
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         36.75
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         8286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                7182
_reflns_number_total             8286
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2746.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220735
_cod_database_fobs_code          2220735
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'
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_
_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'
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_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_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
