#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216558.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_2216558
loop_
_publ_author_name
'Yin, Li-He'
'Wan, Rong'
'Wu, Wen-Yuan'
'Wang, Bin'
'Wang, Jin-Tang'
_publ_section_title
;(R,S)-Diethyl
 {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](phenyl)methyl}phosphonate
;
_journal_coeditor_code           HK2370
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4648
_journal_page_last               o4648
_journal_paper_doi               10.1107/S1600536807056632
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H20 Cl2 N3 O3 P S'
_chemical_formula_moiety         'C19 H20 Cl2 N3 O3 P S'
_chemical_formula_sum            'C19 H20 Cl2 N3 O3 P S'
_chemical_formula_weight         472.31
_chemical_melting_point          .453E-305
_chemical_name_systematic
;(R,S)-Diethyl
{[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](phenyl)methyl}phosphonate
;
_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                90.00
_cell_angle_beta                 94.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4870(17)
_cell_length_b                   16.530(3)
_cell_length_c                   15.703(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     2196.3(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0925
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4609
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  0.9527
_exptl_absorpt_correction_T_min  0.8284
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.698
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4312
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0847
_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)+(0.1265P)²+1.3578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                3145
_reflns_number_total             4312
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2370.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216558
_cod_database_fobs_code          2216558
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
Cl Cl1 0.3460(3) 0.37335(12) 0.14352(10) 0.1114(7) Uani d . 1
Cl Cl2 0.3666(2) 0.44309(12) -0.18670(9) 0.1133(8) Uani d . 1
S S 0.1558(2) 0.48605(11) 0.25006(9) 0.0806(6) Uani d U 1
P P 0.0393(2) 0.65490(13) 0.52266(9) 0.0760(6) Uani d . 1
O O1 0.2180(6) 0.6788(3) 0.5237(2) 0.1143(17) Uani d . 1
O O2 0.0005(6) 0.5841(3) 0.5707(2) 0.1010(16) Uani d . 1
O O3 -0.0427(5) 0.7339(3) 0.5529(2) 0.0810(13) Uani d U 1
N N1 0.0476(5) 0.5763(3) 0.3769(2) 0.0743(15) Uani d U 1
H H1A 0.0697 0.5357 0.4099 0.089 Uiso calc R 1
N N2 0.0586(6) 0.6318(3) 0.2402(3) 0.0777(15) Uani d U 1
N N3 0.1044(6) 0.6122(3) 0.1607(3) 0.0800(16) Uani d U 1
C C1 0.3610(7) 0.6550(4) 0.6493(4) 0.100 Uani d D 1
H H1B 0.4266 0.6728 0.6983 0.150 Uiso calc R 1
H H1C 0.4184 0.6170 0.6174 0.150 Uiso calc R 1
H H1D 0.2679 0.6294 0.6678 0.150 Uiso calc R 1
C C2 0.3175(8) 0.7211(4) 0.5980(4) 0.104 Uani d D 1
H H2C 0.4090 0.7483 0.5780 0.125 Uiso calc R 1
H H2D 0.2548 0.7596 0.6275 0.125 Uiso calc R 1
C C3 -0.1313(9) 0.7382(5) 0.6870(5) 0.139(3) Uani d DU 1
H H3B -0.2156 0.7363 0.7243 0.209 Uiso calc R 1
H H3C -0.0786 0.7895 0.6929 0.209 Uiso calc R 1
H H3D -0.0574 0.6956 0.7017 0.209 Uiso calc R 1
C C4 -0.1941(9) 0.7282(5) 0.6014(4) 0.126(3) Uani d DU 1
H H4A -0.2685 0.7708 0.5842 0.151 Uiso calc R 1
H H4B -0.2454 0.6760 0.5928 0.151 Uiso calc R 1
C C5 -0.0214(6) 0.6487(4) 0.4094(3) 0.0625(16) Uani d U 1
H H5A 0.0225 0.6954 0.3810 0.075 Uiso calc R 1
C C6 -0.1952(8) 0.6534(5) 0.3975(3) 0.0728(17) Uani d DU 1
C C7 -0.2645(8) 0.7291(5) 0.3791(4) 0.094(2) Uani d DU 1
H H7A -0.2045 0.7752 0.3711 0.112 Uiso calc R 1
C C8 -0.4350(10) 0.7307(6) 0.3735(4) 0.114(3) Uani d DU 1
H H8A -0.4841 0.7805 0.3632 0.137 Uiso calc R 1
C C9 -0.5298(10) 0.6650(6) 0.3820(4) 0.107(2) Uani d DU 1
H H9A -0.6394 0.6689 0.3761 0.128 Uiso calc R 1
C C10 -0.4547(10) 0.5930(5) 0.3999(4) 0.105(2) Uani d DU 1
H H10A -0.5146 0.5470 0.4085 0.126 Uiso calc R 1
C C11 -0.2943(8) 0.5873(5) 0.4053(4) 0.091(2) Uani d DU 1
H H11A -0.2487 0.5366 0.4147 0.109 Uiso calc R 1
C C12 0.0776(6) 0.5735(4) 0.2916(3) 0.0647(16) Uani d U 1
C C13 0.1598(7) 0.5399(4) 0.1552(3) 0.0660(17) Uani d DU 1
C C14 0.2134(6) 0.5107(4) 0.0727(3) 0.0646(16) Uani d DU 1
C C15 0.1763(7) 0.5587(4) 0.0007(3) 0.0771(18) Uani d U 1
H H15A 0.1172 0.6056 0.0058 0.092 Uiso calc R 1
C C16 0.2262(7) 0.5374(4) -0.0786(3) 0.0709(17) Uani d U 1
H H16A 0.2031 0.5702 -0.1261 0.085 Uiso calc R 1
C C17 0.3105(7) 0.4667(4) -0.0856(3) 0.0694(17) Uani d U 1
C C18 0.3452(7) 0.4183(4) -0.0185(3) 0.0785(19) Uani d U 1
H H18A 0.4053 0.3718 -0.0239 0.094 Uiso calc R 1
C C19 0.2892(7) 0.4390(4) 0.0592(3) 0.0715(18) Uani d U 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'
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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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
C13 S C12 86.0(3)
O2 P O1 117.3(3)
O2 P O3 113.1(2)
O1 P O3 103.8(3)
O2 P C5 114.0(3)
O1 P C5 103.0(2)
O3 P C5 104.2(3)
C2 O1 P 126.2(4)
C4 O3 P 120.2(4)
C12 N1 C5 118.8(5)
C12 N1 H1A 120.6
C5 N1 H1A 120.6
C12 N2 N3 111.7(5)
C13 N3 N2 114.1(5)
C2 C1 H1B 109.5
C2 C1 H1C 109.5
H1B C1 H1C 109.5
C2 C1 H1D 109.5
H1B C1 H1D 109.5
H1C C1 H1D 109.5
C1 C2 O1 100.7(6)
C1 C2 H2C 111.6
O1 C2 H2C 111.6
C1 C2 H2D 111.6
O1 C2 H2D 111.6
H2C C2 H2D 109.4
C4 C3 H3B 109.5
C4 C3 H3C 109.5
H3B C3 H3C 109.5
C4 C3 H3D 109.5
H3B C3 H3D 109.5
H3C C3 H3D 109.5
C3 C4 O3 101.2(6)
C3 C4 H4A 111.5
O3 C4 H4A 111.5
C3 C4 H4B 111.5
O3 C4 H4B 111.5
H4A C4 H4B 109.3
N1 C5 C6 115.4(5)
N1 C5 P 107.6(4)
C6 C5 P 109.0(3)
N1 C5 H5A 108.2
C6 C5 H5A 108.2
P C5 H5A 108.2
C11 C6 C7 118.2(7)
C11 C6 C5 123.5(7)
C7 C6 C5 118.2(7)
C6 C7 C8 115.6(8)
C6 C7 H7A 122.2
C8 C7 H7A 122.2
C9 C8 C7 125.1(9)
C9 C8 H8A 117.4
C7 C8 H8A 117.4
C8 C9 C10 116.3(8)
C8 C9 H9A 121.8
C10 C9 H9A 121.8
C11 C10 C9 121.4(8)
C11 C10 H10A 119.3
C9 C10 H10A 119.3
C10 C11 C6 123.2(8)
C10 C11 H11A 118.4
C6 C11 H11A 118.4
N2 C12 N1 124.8(6)
N2 C12 S 115.4(4)
N1 C12 S 119.7(5)
N3 C13 C14 119.7(5)
N3 C13 S 112.7(4)
C14 C13 S 127.5(5)
C19 C14 C15 116.3(5)
C19 C14 C13 126.4(6)
C15 C14 C13 117.2(6)
C16 C15 C14 121.0(6)
C16 C15 H15A 119.5
C14 C15 H15A 119.5
C17 C16 C15 118.8(6)
C17 C16 H16A 120.6
C15 C16 H16A 120.6
C18 C17 C16 121.9(6)
C18 C17 Cl2 121.7(6)
C16 C17 Cl2 116.4(5)
C17 C18 C19 118.4(6)
C17 C18 H18A 120.8
C19 C18 H18A 120.8
C14 C19 C18 123.2(6)
C14 C19 Cl1 121.5(4)
C18 C19 Cl1 114.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C19 1.751(6)
Cl2 C17 1.737(5)
S C13 1.737(6)
S C12 1.738(6)
P O2 1.444(4)
P O1 1.567(5)
P O3 1.570(4)
P C5 1.815(5)
O1 C2 1.552(7)
O3 C4 1.547(7)
N1 C12 1.383(6)
N1 C5 1.443(6)
N1 H1A 0.8600
N2 C12 1.260(7)
N2 N3 1.376(5)
N3 C13 1.289(7)
C1 C2 1.391(7)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
C2 H2C 0.9700
C2 H2D 0.9700
C3 C4 1.416(8)
C3 H3B 0.9600
C3 H3C 0.9600
C3 H3D 0.9600
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.475(7)
C5 H5A 0.9800
C6 C11 1.391(8)
C6 C7 1.402(9)
C7 C8 1.443(9)
C7 H7A 0.9300
C8 C9 1.365(10)
C8 H8A 0.9300
C9 C10 1.368(10)
C9 H9A 0.9300
C10 C11 1.361(9)
C10 H10A 0.9300
C11 H11A 0.9300
C13 C14 1.487(6)
C14 C19 1.372(8)
C14 C15 1.397(7)
C15 C16 1.392(7)
C15 H15A 0.9300
C16 C17 1.379(8)
C16 H16A 0.9300
C17 C18 1.338(8)
C18 C19 1.387(7)
C18 H18A 0.9300
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 H1A O2 3_566 0.86 2.09 2.815(7) 141 yes
C4 H4A N3 4_576 0.97 2.56 3.321(11) 134 yes
C15 H15A N3 . 0.93 2.45 2.783(7) 101 yes
