#------------------------------------------------------------------------------
#$Date: 2012-02-25 23:26:40 +0000 (Sat, 25 Feb 2012) $
#$Revision: 35014 $
#$URL: svn://www.crystallography.net/cod/cif/1/1501657.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501657
loop_
_publ_author_name
'Wang, Huan'
'Yang, Zhikun'
'Fan, Zhijin'
'Wu, Qingjun'
'Zhang, Youjun'
'Mi, Na'
'Wang, Shouxin'
'Zhang, Zhengcai'
'Song, Haibin'
'Liu, Feng'
_publ_section_title
;
 Synthesis and insecticidal activity of N-tert-butyl-N,N'-diacylhydrazines
 containing 1,2,3-thiadiazoles.
;
_journal_issue                   2
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              628
_journal_page_last               634
_journal_volume                  59
_journal_year                    2011
_chemical_formula_sum            'C16 H20 N4 O2 S'
_chemical_formula_weight         332.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.724(2)
_cell_length_b                   9.2465(18)
_cell_length_c                   15.567(3)
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.868
_cell_measurement_theta_min      2.565
_cell_volume                     1680.4(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11153
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.318(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0547
_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/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                2073
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    jf104004q_si_001.cif
_[local]_cod_data_source_block   r91027b
_[local]_cod_cif_authors_sg_H-M  P2(1)/c
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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_cell_volume        1680.5(6)
_cod_database_code               1501657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.40904(5) 0.47821(7) 0.09597(4) 0.0261(3) Uani 1 1 d .
O1 O 0.16277(13) 0.50376(19) 0.25269(12) 0.0292(5) Uani 1 1 d .
O2 O 0.49279(13) 0.65177(16) 0.31152(12) 0.0224(4) Uani 1 1 d .
N1 N 0.3593(2) 0.5488(2) 0.00151(15) 0.0332(6) Uani 1 1 d .
N2 N 0.2568(2) 0.6012(2) 0.00454(15) 0.0351(6) Uani 1 1 d .
N3 N 0.34343(14) 0.42950(19) 0.29256(13) 0.0160(5) Uani 1 1 d .
N4 N 0.45579(15) 0.4217(2) 0.26978(14) 0.0173(5) Uani 1 1 d D
C1 C 0.0953(2) 0.6410(4) 0.0916(2) 0.0465(9) Uani 1 1 d .
H1A H 0.0706 0.6984 0.0419 0.070 Uiso 1 1 calc R
H1B H 0.0954 0.6993 0.1426 0.070 Uiso 1 1 calc R
H1C H 0.0439 0.5609 0.0955 0.070 Uiso 1 1 calc R
C2 C 0.2137(2) 0.5856(3) 0.08326(18) 0.0280(6) Uani 1 1 d .
C3 C 0.2884(2) 0.5178(2) 0.14400(17) 0.0208(6) Uani 1 1 d .
C4 C 0.2601(2) 0.4846(2) 0.23386(17) 0.0193(6) Uani 1 1 d .
C5 C 0.32025(19) 0.3994(2) 0.38533(16) 0.0188(6) Uani 1 1 d .
C6 C 0.2274(2) 0.2832(3) 0.38636(18) 0.0292(7) Uani 1 1 d .
H6A H 0.1568 0.3197 0.3586 0.044 Uiso 1 1 calc R
H6B H 0.2169 0.2580 0.4449 0.044 Uiso 1 1 calc R
H6C H 0.2503 0.1990 0.3562 0.044 Uiso 1 1 calc R
C7 C 0.2860(2) 0.5387(2) 0.42865(18) 0.0245(6) Uani 1 1 d .
H7A H 0.3458 0.6091 0.4262 0.037 Uiso 1 1 calc R
H7B H 0.2743 0.5193 0.4878 0.037 Uiso 1 1 calc R
H7C H 0.2164 0.5753 0.3992 0.037 Uiso 1 1 calc R
C8 C 0.4295(2) 0.3408(3) 0.43309(17) 0.0268(6) Uani 1 1 d .
H8A H 0.4526 0.2546 0.4050 0.040 Uiso 1 1 calc R
H8B H 0.4159 0.3188 0.4915 0.040 Uiso 1 1 calc R
H8C H 0.4890 0.4121 0.4329 0.040 Uiso 1 1 calc R
C9 C 0.52822(19) 0.5351(2) 0.28711(16) 0.0166(5) Uani 1 1 d .
C10 C 0.65121(19) 0.5102(2) 0.27661(17) 0.0180(6) Uani 1 1 d .
C11 C 0.69010(19) 0.4093(2) 0.21897(17) 0.0210(6) Uani 1 1 d .
H11 H 0.6383 0.3524 0.1851 0.025 Uiso 1 1 calc R
C12 C 0.80637(19) 0.3955(3) 0.21299(18) 0.0259(6) Uani 1 1 d .
H12 H 0.8328 0.3290 0.1746 0.031 Uiso 1 1 calc R
C13 C 0.8842(2) 0.4797(3) 0.26360(18) 0.0251(6) Uani 1 1 d .
H13 H 0.9622 0.4686 0.2589 0.030 Uiso 1 1 calc R
C14 C 0.84695(19) 0.5806(3) 0.32140(18) 0.0237(6) Uani 1 1 d .
C15 C 0.73018(18) 0.5956(2) 0.32645(16) 0.0198(6) Uani 1 1 d .
H15 H 0.7038 0.6638 0.3638 0.024 Uiso 1 1 d R
C16 C 0.9317(2) 0.6727(3) 0.3760(2) 0.0387(8) Uani 1 1 d .
H16A H 1.0063 0.6627 0.3557 0.058 Uiso 1 1 calc R
H16B H 0.9345 0.6419 0.4350 0.058 Uiso 1 1 calc R
H16C H 0.9084 0.7722 0.3718 0.058 Uiso 1 1 calc R
H4 H 0.4780(17) 0.3341(14) 0.2539(16) 0.018(6) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0286(4) 0.0335(4) 0.0172(4) 0.0012(3) 0.0075(3) -0.0037(3)
O1 0.0142(9) 0.0493(11) 0.0245(12) 0.0042(9) 0.0037(8) 0.0042(8)
O2 0.0223(9) 0.0173(9) 0.0285(11) -0.0024(7) 0.0076(8) 0.0001(7)
N1 0.0451(15) 0.0384(13) 0.0168(14) 0.0047(10) 0.0073(11) -0.0062(11)
N2 0.0503(16) 0.0349(13) 0.0199(14) 0.0047(10) 0.0023(12) 0.0012(11)
N3 0.0125(10) 0.0213(10) 0.0145(12) 0.0008(8) 0.0023(9) 0.0014(8)
N4 0.0154(10) 0.0167(10) 0.0205(13) -0.0026(9) 0.0052(9) 0.0001(8)
C1 0.0468(19) 0.060(2) 0.0300(19) 0.0049(16) -0.0081(15) 0.0229(16)
C2 0.0370(15) 0.0275(14) 0.0189(16) -0.0003(11) -0.0002(12) 0.0031(11)
C3 0.0212(13) 0.0236(12) 0.0175(15) -0.0004(10) 0.0010(11) -0.0032(10)
C4 0.0198(14) 0.0219(12) 0.0158(14) -0.0005(10) -0.0001(11) -0.0029(10)
C5 0.0191(12) 0.0221(12) 0.0150(14) 0.0012(10) 0.0018(10) 0.0001(10)
C6 0.0320(15) 0.0321(14) 0.0248(16) 0.0015(12) 0.0102(13) -0.0075(11)
C7 0.0291(14) 0.0274(13) 0.0174(15) -0.0014(11) 0.0039(11) 0.0029(11)
C8 0.0312(15) 0.0294(14) 0.0195(16) 0.0060(11) 0.0009(12) 0.0046(11)
C9 0.0183(13) 0.0187(12) 0.0131(14) 0.0026(10) 0.0024(10) 0.0015(10)
C10 0.0175(12) 0.0189(12) 0.0178(14) 0.0040(10) 0.0028(10) -0.0007(9)
C11 0.0176(13) 0.0225(12) 0.0229(15) -0.0023(10) 0.0021(11) -0.0026(10)
C12 0.0225(14) 0.0268(13) 0.0295(17) -0.0015(11) 0.0079(12) 0.0044(11)
C13 0.0146(12) 0.0332(14) 0.0277(17) 0.0040(12) 0.0026(12) 0.0012(10)
C14 0.0189(13) 0.0275(13) 0.0242(16) 0.0038(11) -0.0006(11) -0.0015(10)
C15 0.0210(13) 0.0222(13) 0.0164(15) -0.0009(10) 0.0027(11) -0.0015(10)
C16 0.0253(15) 0.0520(18) 0.038(2) -0.0079(15) -0.0030(14) -0.0077(13)
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'
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
N1 S1 C3 93.79(12)
N2 N1 S1 111.34(18)
N1 N2 C2 114.2(2)
C4 N3 N4 118.7(2)
C4 N3 C5 121.48(19)
N4 N3 C5 119.12(18)
C9 N4 N3 119.72(19)
C9 N4 H4 124.2(14)
N3 N4 H4 115.0(14)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N2 C2 C3 113.4(2)
N2 C2 C1 117.4(2)
C3 C2 C1 129.2(3)
C2 C3 C4 123.5(2)
C2 C3 S1 107.3(2)
C4 C3 S1 129.1(2)
O1 C4 N3 121.3(2)
O1 C4 C3 119.2(2)
N3 C4 C3 119.5(2)
N3 C5 C8 108.30(19)
N3 C5 C7 110.05(19)
C8 C5 C7 109.2(2)
N3 C5 C6 109.1(2)
C8 C5 C6 108.2(2)
C7 C5 C6 111.8(2)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 N4 121.0(2)
O2 C9 C10 122.0(2)
N4 C9 C10 117.0(2)
C15 C10 C11 119.6(2)
C15 C10 C9 116.9(2)
C11 C10 C9 123.4(2)
C12 C11 C10 119.1(2)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C12 C13 120.8(2)
C11 C12 H12 119.6
C13 C12 H12 119.6
C12 C13 C14 120.9(2)
C12 C13 H13 119.6
C14 C13 H13 119.6
C15 C14 C13 118.2(2)
C15 C14 C16 121.0(2)
C13 C14 C16 120.8(2)
C14 C15 C10 121.4(2)
C14 C15 H15 119.3
C10 C15 H15 119.3
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.664(2)
S1 C3 1.699(3)
O1 C4 1.217(3)
O2 C9 1.229(3)
N1 N2 1.301(3)
N2 C2 1.375(4)
N3 C4 1.373(3)
N3 N4 1.397(3)
N3 C5 1.519(3)
N4 C9 1.360(3)
N4 H4 0.893(10)
C1 C2 1.497(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.379(4)
C3 C4 1.499(4)
C5 C8 1.521(3)
C5 C7 1.524(3)
C5 C6 1.530(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.484(3)
C10 C15 1.397(3)
C10 C11 1.399(3)
C11 C12 1.381(3)
C11 H11 0.9300
C12 C13 1.389(4)
C12 H12 0.9300
C13 C14 1.394(4)
C13 H13 0.9300
C14 C15 1.385(3)
C14 C16 1.510(4)
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C3 S1 N1 N2 0.33(19)
S1 N1 N2 C2 -0.4(3)
C4 N3 N4 C9 90.1(3)
C5 N3 N4 C9 -80.5(3)
N1 N2 C2 C3 0.4(3)
N1 N2 C2 C1 -179.0(2)
N2 C2 C3 C4 -178.3(2)
C1 C2 C3 C4 1.0(4)
N2 C2 C3 S1 -0.1(3)
C1 C2 C3 S1 179.2(2)
N1 S1 C3 C2 -0.12(18)
N1 S1 C3 C4 177.9(2)
N4 N3 C4 O1 -174.5(2)
C5 N3 C4 O1 -4.1(3)
N4 N3 C4 C3 7.3(3)
C5 N3 C4 C3 177.67(19)
C2 C3 C4 O1 8.0(4)
S1 C3 C4 O1 -169.73(18)
C2 C3 C4 N3 -173.7(2)
S1 C3 C4 N3 8.5(3)
C4 N3 C5 C8 -179.51(19)
N4 N3 C5 C8 -9.2(3)
C4 N3 C5 C7 -60.2(3)
N4 N3 C5 C7 110.1(2)
C4 N3 C5 C6 62.9(3)
N4 N3 C5 C6 -126.8(2)
N3 N4 C9 O2 -10.1(4)
N3 N4 C9 C10 168.9(2)
O2 C9 C10 C15 25.6(3)
N4 C9 C10 C15 -153.4(2)
O2 C9 C10 C11 -153.0(2)
N4 C9 C10 C11 28.0(4)
C15 C10 C11 C12 0.5(4)
C9 C10 C11 C12 179.1(2)
C10 C11 C12 C13 0.3(4)
C11 C12 C13 C14 -0.3(4)
C12 C13 C14 C15 -0.5(4)
C12 C13 C14 C16 -179.6(2)
C13 C14 C15 C10 1.3(4)
C16 C14 C15 C10 -179.6(2)
C11 C10 C15 C14 -1.3(4)
C9 C10 C15 C14 180.0(2)