#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/29/2012923.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_2012923
loop_
_publ_author_name
'El Hazazi, S.'
'Baouid, A.'
'Hasnaoui, A.'
'Pierrot, M.'
_publ_section_title
;Ethyl
 5-[2-(2-aminophénylimino)-2-phényléthylidène]-4-(4-chlorophényl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate
 et éthyl
 5-{2-[2-(méthylamino)phénylimino]-2-phényléthylidène}-4-(4-nitrophényl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o585
_journal_page_last               o588
_journal_paper_doi               10.1107/S0108270102012647
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C25 H21 Cl N4 O2 S'
_chemical_formula_structural     'C25 H21 Cl N4 O2 S'
_chemical_formula_sum            'C25 H21 Cl N4 O2 S'
_chemical_formula_weight         476.97
_chemical_name_systematic
;
Ethyl 5-[2-(2-aminophenylimino)-2-phenylethylidene]-
4-(4-chlorophenyl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.667(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.98260(10)
_cell_length_b                   9.5040(2)
_cell_length_c                   25.0790(10)
_cell_measurement_reflns_used    26069
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      3.0
_cell_volume                     2379.20(11)
_computing_cell_refinement       'KappaCCD Reference Manual'
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction
'DENZO et SCALEPACK (Otwinoski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       φ
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26069
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0670P)²+0.7595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.123
_refine_ls_wR_factor_ref         0.145
_reflns_number_gt                3903
_reflns_number_total             4247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1014.cif
_cod_data_source_block           IIIa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2379.30(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012923
_cod_database_fobs_code          2012923
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_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
_atom_site_type_symbol
Cl1 0.39057(8) 0.44576(11) 0.59178(4) 0.0919(3) Uani d . 1 . . Cl
S1 1.14515(5) 0.15588(5) 0.492347(19) 0.04240(17) Uani d . 1 . . S
O29 1.1594(2) 0.0109(2) 0.64135(7) 0.0748(6) Uani d . 1 . . O
O30 1.29502(16) -0.01495(17) 0.57121(7) 0.0552(4) Uani d . 1 . . O
N3 0.92569(16) 0.23524(17) 0.53462(6) 0.0395(4) Uani d . 1 . . N
N4 0.98853(18) 0.16191(17) 0.57447(6) 0.0418(4) Uani d . 1 . . N
N8 1.13385(19) 0.2502(2) 0.39102(7) 0.0505(4) Uani d . 1 . . N
N15 1.2142(3) 0.0176(3) 0.33324(11) 0.0855(8) Uani d . 1 . . N
H15A 1.1303 0.0153 0.3471 0.103 Uiso d R 1 . . H
H15B 1.2258 -0.0560 0.3099 0.103 Uiso d R 1 . . H
C2 0.99095(19) 0.24284(19) 0.48607(7) 0.0370(4) Uani d . 1 . . C
C5 1.1025(2) 0.1164(2) 0.55829(8) 0.0413(4) Uani d . 1 . . C
C6 0.9427(2) 0.3049(2) 0.44103(7) 0.0417(4) Uani d . 1 . . C
H6 0.8555 0.3471 0.4420 0.050 Uiso d R 1 . . H
C7 1.0178(2) 0.3097(2) 0.39246(7) 0.0408(4) Uani d . 1 . . C
C9 1.2198(2) 0.2686(3) 0.34702(8) 0.0519(5) Uani d . 1 . . C
C10 1.2707(3) 0.3993(3) 0.33380(10) 0.0611(6) Uani d . 1 . . C
H10 1.2377 0.4817 0.3515 0.073 Uiso d R 1 . . H
C11 1.3678(3) 0.4127(4) 0.29511(13) 0.0800(8) Uani d . 1 . . C
H11 1.4063 0.5025 0.2868 0.096 Uiso d R 1 . . H
C12 1.4110(3) 0.2940(4) 0.26860(13) 0.0888(10) Uani d . 1 . . C
H12 1.4778 0.3011 0.2415 0.107 Uiso d R 1 . . H
C13 1.3591(3) 0.1647(4) 0.28033(12) 0.0782(9) Uani d . 1 . . C
H13 1.3883 0.0828 0.2614 0.094 Uiso d R 1 . . H
C14 1.2630(3) 0.1487(3) 0.31950(9) 0.0619(7) Uani d . 1 . . C
C16 0.9523(2) 0.3850(2) 0.34670(7) 0.0416(4) Uani d . 1 . . C
C17 0.9295(3) 0.3169(3) 0.29856(9) 0.0584(6) Uani d . 1 . . C
H17 0.9596 0.2218 0.2938 0.070 Uiso d R 1 . . H
C18 0.8637(3) 0.3882(3) 0.25742(10) 0.0735(8) Uani d . 1 . . C
H18 0.8464 0.3412 0.2241 0.088 Uiso d R 1 . . H
C19 0.8241(3) 0.5261(3) 0.26377(11) 0.0719(8) Uani d . 1 . . C
H19 0.7769 0.5742 0.2356 0.086 Uiso d R 1 . . H
C20 0.8500(3) 0.5936(3) 0.31084(11) 0.0679(7) Uani d . 1 . . C
H20 0.8255 0.6907 0.3148 0.081 Uiso d R 1 . . H
C21 0.9125(2) 0.5232(2) 0.35239(9) 0.0542(5) Uani d . 1 . . C
H21 0.9284 0.5701 0.3858 0.065 Uiso d R 1 . . H
C22 0.79537(19) 0.2877(2) 0.54588(7) 0.0388(4) Uani d . 1 . . C
C23 0.7605(2) 0.4244(2) 0.53387(8) 0.0442(4) Uani d . 1 . . C
H23 0.8227 0.4857 0.5164 0.053 Uiso d R 1 . . H
C24 0.6339(2) 0.4728(2) 0.54702(9) 0.0539(5) Uani d . 1 . . C
H24 0.6063 0.5669 0.5385 0.065 Uiso d R 1 . . H
C25 0.5470(2) 0.3849(3) 0.57253(9) 0.0566(6) Uani d . 1 . . C
C26 0.5822(3) 0.2496(3) 0.58504(12) 0.0681(7) Uani d . 1 . . C
H26 0.5192 0.1904 0.6030 0.082 Uiso d R 1 . . H
C27 0.7066(2) 0.1994(3) 0.57114(11) 0.0575(6) Uani d . 1 . . C
H27 0.7314 0.1042 0.5793 0.069 Uiso d R 1 . . H
C28 1.1870(2) 0.0327(2) 0.59589(8) 0.0479(5) Uani d . 1 . . C
C31 1.3844(3) -0.1040(3) 0.60327(11) 0.0650(7) Uani d . 1 . . C
H31A 1.4225 -0.0486 0.6317 0.078 Uiso d R 1 . . H
H31B 1.3339 -0.1802 0.6181 0.078 Uiso d R 1 . . H
C32 1.4901(3) -0.1541(3) 0.56716(14) 0.0840(10) Uani d . 1 . . C
H32A 1.5521 -0.2132 0.5863 0.101 Uiso d R 1 . . H
H32B 1.5371 -0.0753 0.5524 0.101 Uiso d R 1 . . H
H32C 1.4485 -0.2070 0.5389 0.101 Uiso d R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 S1 C5 87.89(9) yes
C28 O30 C31 115.71(19) ?
N4 N3 C2 116.86(16) yes
N4 N3 C22 116.52(15) ?
C2 N3 C22 126.45(15) ?
C5 N4 N3 109.96(16) yes
C7 N8 C9 121.31(17) yes
C14 N15 H15A 116.4 ?
C14 N15 H15B 118.6 ?
H15A N15 H15B 110.4 ?
C6 C2 N3 125.89(18) ?
C6 C2 S1 125.61(15) ?
N3 C2 S1 108.49(13) yes
N4 C5 C28 118.45(18) ?
N4 C5 S1 116.76(14) yes
C28 C5 S1 124.78(15) ?
C2 C6 C7 122.35(18) yes
C2 C6 H6 118.3 ?
C7 C6 H6 119.4 ?
N8 C7 C6 119.12(17) yes
N8 C7 C16 124.96(18) ?
C6 C7 C16 115.92(17) ?
C10 C9 C14 119.7(2) ?
C10 C9 N8 121.7(2) ?
C14 C9 N8 118.4(2) ?
C9 C10 C11 120.8(3) ?
C9 C10 H10 119.5 ?
C11 C10 H10 119.7 ?
C12 C11 C10 119.2(3) ?
C12 C11 H11 119.6 ?
C10 C11 H11 121.2 ?
C13 C12 C11 120.6(3) ?
C13 C12 H12 118.9 ?
C11 C12 H12 120.4 ?
C12 C13 C14 121.1(3) ?
C12 C13 H13 120.3 ?
C14 C13 H13 118.5 ?
N15 C14 C13 121.5(2) ?
N15 C14 C9 119.9(2) ?
C13 C14 C9 118.5(3) ?
C21 C16 C17 119.35(19) ?
C21 C16 C7 119.96(18) ?
C17 C16 C7 120.68(19) ?
C16 C17 C18 119.3(2) ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.8 ?
C19 C18 C17 120.7(3) ?
C19 C18 H18 119.6 ?
C17 C18 H18 119.8 ?
C20 C19 C18 119.7(2) ?
C20 C19 H19 119.9 ?
C18 C19 H19 120.4 ?
C19 C20 C21 120.2(3) ?
C19 C20 H20 119.7 ?
C21 C20 H20 120.1 ?
C16 C21 C20 120.7(2) ?
C16 C21 H21 119.1 ?
C20 C21 H21 120.1 ?
C23 C22 C27 120.82(19) ?
C23 C22 N3 121.05(18) ?
C27 C22 N3 118.08(17) ?
C22 C23 C24 119.3(2) ?
C22 C23 H23 120.6 ?
C24 C23 H23 120.2 ?
C25 C24 C23 119.5(2) ?
C25 C24 H24 119.4 ?
C23 C24 H24 121.0 ?
C26 C25 C24 121.2(2) ?
C26 C25 Cl1 118.5(2) ?
C24 C25 Cl1 120.18(19) ?
C25 C26 C27 119.8(2) ?
C25 C26 H26 119.4 ?
C27 C26 H26 120.8 ?
C26 C27 C22 119.4(2) ?
C26 C27 H27 120.2 ?
C22 C27 H27 120.4 ?
O29 C28 O30 125.65(19) ?
O29 C28 C5 124.2(2) ?
O30 C28 C5 110.10(18) ?
O30 C31 C32 106.6(2) ?
O30 C31 H31A 108.9 ?
C32 C31 H31A 110.6 ?
O30 C31 H31B 109.2 ?
C32 C31 H31B 112.1 ?
H31A C31 H31B 109.4 ?
C31 C32 H32A 110.0 ?
C31 C32 H32B 109.9 ?
H32A C32 H32B 109.5 ?
C31 C32 H32C 108.4 ?
H32A C32 H32C 109.5 ?
H32B C32 H32C 109.5 ?
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
Cl1 C25 . 1.739(2) ?
S1 C2 . 1.7526(19) yes
S1 C5 . 1.753(2) yes
O29 C28 . 1.194(3) ?
O30 C28 . 1.329(3) ?
O30 C31 . 1.463(2) ?
N3 N4 . 1.365(2) yes
N3 C2 . 1.389(2) yes
N3 C22 . 1.425(2) ?
N4 C5 . 1.287(3) yes
N8 C7 . 1.290(3) yes
N8 C9 . 1.417(3) yes
N15 C14 . 1.383(4) ?
N15 H15A . 0.9112 ?
N15 H15B . 0.9196 ?
C2 C6 . 1.358(3) yes
C5 C28 . 1.488(3) ?
C6 C7 . 1.439(3) yes
C6 H6 . 0.9590 ?
C7 C16 . 1.497(3) ?
C9 C10 . 1.384(4) ?
C9 C14 . 1.403(3) ?
C10 C11 . 1.385(4) ?
C10 H10 . 0.9604 ?
C11 C12 . 1.381(5) ?
C11 H11 . 0.9599 ?
C12 C13 . 1.367(5) ?
C12 H12 . 0.9599 ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.9590 ?
C16 C21 . 1.380(3) ?
C16 C17 . 1.386(3) ?
C17 C18 . 1.393(4) ?
C17 H17 . 0.9604 ?
C18 C19 . 1.378(5) ?
C18 H18 . 0.9614 ?
C19 C20 . 1.366(4) ?
C19 H19 . 0.9606 ?
C20 C21 . 1.381(3) ?
C20 H20 . 0.9602 ?
C21 H21 . 0.9604 ?
C22 C23 . 1.377(3) ?
C22 C27 . 1.380(3) ?
C23 C24 . 1.388(3) ?
C23 H23 . 0.9608 ?
C24 C25 . 1.369(4) ?
C24 H24 . 0.9591 ?
C25 C26 . 1.368(4) ?
C26 C27 . 1.379(4) ?
C26 H26 . 0.9600 ?
C27 H27 . 0.9595 ?
C31 C32 . 1.478(4) ?
C31 H31A . 0.9609 ?
C31 H31B . 0.9597 ?
C32 H32A . 0.9605 ?
C32 H32B . 0.9601 ?
C32 H32C . 0.9592 ?
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
N15 H15A N4 3_756 0.91 2.86 3.532(3) 132
N15 H15A O29 3_756 0.91 2.92 3.801(3) 162
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181747
