#------------------------------------------------------------------------------
#$Date: 2008-02-04 17:24:24 +0000 (Mon, 04 Feb 2008) $
#$Revision: 87 $
#$URL: svn://www.crystallography.net/cod/cif/2/2204473.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_2204473
loop_
_publ_author_name
'Chopra, Deepak'
'Choudhury, A. R'
'Nagarajan, K.'
'Guru Row, T. N.'
_publ_section_title
;
4-(2-Methylprop-2-enyl)-1-[3-(trifluoromethyl)phenyl]thiosemicarbazide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2017
_journal_page_last               o2018
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C12 H14 F3 N3 S1'
_chemical_formula_moiety         'C12 H14 F3 N3 S1'
_chemical_formula_sum            'C12 H14 F3 N3 S1'
_chemical_formula_weight         289.31
_chemical_name_systematic
;
4-(2-Methylprop-2-enyl)-1-[3-(trifluoromethyl)phenyl]thiosemicarbazide
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.387(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.964(2)
_cell_length_b                   6.0900(8)
_cell_length_c                   15.754(2)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      1.4
_cell_volume                     1362.3(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10483
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.70
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.9405
_exptl_absorpt_correction_T_min  0.9126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.41
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             599.9
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0763
_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/[\s^2^(Fo^2^)+(0.2P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2490
_reflns_number_gt                1741
_reflns_number_total             2913
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_original_file       cv6385.cif
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
F1 0.567(2) 0.241(6) 0.051(2) 0.130(4) Uani d P 0.228(9) A 1 F
F2 0.5042(18) 0.297(4) 0.0411(14) 0.094(2) Uani d P 0.228(9) A 1 F
F3 0.546(2) 0.011(4) 0.1180(12) 0.113(3) Uani d P 0.228(9) A 1 F
F1A 0.5855(5) 0.1167(17) 0.0664(6) 0.130(4) Uani d P 0.772(9) A 2 F
F2A 0.4561(5) 0.2988(9) 0.0586(4) 0.094(2) Uani d P 0.772(9) A 2 F
F3A 0.4877(6) 0.0197(9) 0.1297(3) 0.113(3) Uani d P 0.772(9) A 2 F
S1 0.59913(8) -0.26039(17) 0.53618(8) 0.0476(4) Uani d . 1 . . S
N1 0.6609(3) 0.2936(6) 0.4403(2) 0.0408(9) Uani d . 1 . . N
N2 0.6126(3) 0.1058(6) 0.4521(2) 0.0430(9) Uani d . 1 . . N
N3 0.7529(3) -0.0415(6) 0.5329(2) 0.0443(9) Uani d . 1 . . N
C1 0.6441(3) 0.3650(6) 0.3515(3) 0.0367(9) Uani d . 1 A . C
C2 0.5944(3) 0.2426(6) 0.2768(3) 0.0364(9) Uani d . 1 . . C
C3 0.5836(3) 0.3252(7) 0.1921(3) 0.0386(9) Uani d . 1 A . C
C4 0.6208(3) 0.5265(7) 0.1801(3) 0.0444(10) Uani d . 1 . . C
C5 0.6705(3) 0.6460(7) 0.2543(3) 0.0444(10) Uani d . 1 A . C
C6 0.6827(3) 0.5678(6) 0.3392(3) 0.0417(10) Uani d . 1 . . C
C7 0.5310(4) 0.1970(8) 0.1115(3) 0.0498(11) Uani d . 1 . . C
C8 0.6596(3) -0.0543(6) 0.5071(2) 0.0342(9) Uani d . 1 . . C
C9 0.8170(3) -0.1715(8) 0.6036(3) 0.0502(11) Uani d . 1 . . C
C10 0.8445(3) -0.0670(8) 0.6944(3) 0.0482(11) Uani d . 1 . . C
C11 0.9105(4) -0.2019(10) 0.7668(3) 0.0667(15) Uani d . 1 . . C
C13 0.8142(4) 0.1270(10) 0.7094(4) 0.0714(15) Uani d . 1 . . C
H1N 0.651(3) 0.385(7) 0.470(3) 0.035(12) Uiso d . 1 . . H
H2N 0.565(3) 0.116(7) 0.447(3) 0.022(11) Uiso d . 1 . . H
H3N 0.770(3) 0.079(8) 0.516(3) 0.048(13) Uiso d . 1 . . H
H2 0.5687 0.1073 0.2836 0.044 Uiso calc R 1 A . H
H4 0.6123 0.5803 0.1228 0.053 Uiso calc R 1 A . H
H5 0.6962 0.7811 0.2469 0.053 Uiso calc R 1 . . H
H6 0.7167 0.6498 0.3886 0.050 Uiso calc R 1 A . H
H9A 0.8737 -0.1996 0.5879 0.060 Uiso calc R 1 . . H
H9B 0.7877 -0.3121 0.6067 0.060 Uiso calc R 1 . . H
H11A 0.9695 -0.2167 0.7555 0.100 Uiso calc R 1 . . H
H11B 0.8837 -0.3447 0.7680 0.100 Uiso calc R 1 . . H
H11C 0.9204 -0.1309 0.8235 0.100 Uiso calc R 1 . . H
H13A 0.8336 0.1856 0.7668 0.086 Uiso calc R 1 . . H
H13B 0.7732 0.2058 0.6625 0.086 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.082(4) 0.191(10) 0.120(5) -0.015(5) 0.039(3) -0.115(7)
F2 0.069(4) 0.104(3) 0.075(3) 0.031(3) -0.027(3) -0.027(2)
F3 0.173(7) 0.102(3) 0.052(2) -0.104(4) 0.018(3) -0.009(2)
F1A 0.082(4) 0.191(10) 0.120(5) -0.015(5) 0.039(3) -0.115(7)
F2A 0.069(4) 0.104(3) 0.075(3) 0.031(3) -0.027(3) -0.027(2)
F3A 0.173(7) 0.102(3) 0.052(2) -0.104(4) 0.018(3) -0.009(2)
S1 0.0564(7) 0.0402(7) 0.0513(7) 0.0022(5) 0.0242(5) 0.0056(5)
N1 0.053(2) 0.0335(19) 0.0355(18) -0.0036(15) 0.0137(16) -0.0022(15)
N2 0.039(2) 0.044(2) 0.047(2) 0.0020(18) 0.0152(17) 0.0092(16)
N3 0.047(2) 0.041(2) 0.044(2) 0.0016(17) 0.0132(16) 0.0009(16)
C1 0.038(2) 0.034(2) 0.038(2) 0.0049(17) 0.0129(16) 0.0041(16)
C2 0.037(2) 0.0306(19) 0.042(2) -0.0037(16) 0.0133(16) -0.0001(16)
C3 0.038(2) 0.036(2) 0.040(2) 0.0004(16) 0.0099(17) -0.0014(16)
C4 0.053(3) 0.038(2) 0.043(2) -0.0025(19) 0.0162(19) 0.0070(18)
C5 0.052(2) 0.030(2) 0.053(2) -0.0015(19) 0.020(2) 0.0034(18)
C6 0.044(2) 0.037(2) 0.045(2) -0.0030(18) 0.0158(18) -0.0062(17)
C7 0.062(3) 0.043(3) 0.039(2) -0.003(2) 0.009(2) -0.0019(18)
C8 0.042(2) 0.034(2) 0.0288(18) 0.0004(17) 0.0146(16) -0.0035(15)
C9 0.045(2) 0.050(2) 0.052(3) 0.012(2) 0.010(2) 0.000(2)
C10 0.042(2) 0.057(3) 0.047(2) 0.002(2) 0.0162(19) 0.002(2)
C11 0.057(3) 0.084(4) 0.052(3) 0.006(3) 0.006(2) 0.009(3)
C13 0.085(4) 0.073(4) 0.053(3) 0.007(3) 0.019(3) -0.012(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 F2A 1.321(7)
C7 F1A 1.333(8)
C7 F3A 1.336(7)
C7 C3 1.486(6)
S1 C8 1.693(4)
N3 C8 1.328(5)
N3 C9 1.454(5)
N3 H3N 0.85(5)
N1 N2 1.396(5)
N1 C1 1.411(5)
N1 H1N 0.77(5)
N2 C8 1.346(5)
N2 H2N 0.70(4)
C3 C4 1.384(6)
C3 C2 1.387(6)
C1 C2 1.393(5)
C1 C6 1.403(6)
C2 H2 0.9300
C10 C13 1.314(7)
C10 C11 1.497(6)
C10 C9 1.500(6)
C9 H9A 0.9700
C9 H9B 0.9700
C6 C5 1.377(6)
C6 H6 0.9300
C4 C5 1.379(6)
C4 H4 0.9300
C5 H5 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C13 H13A 0.9300
C13 H13B 0.9300
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F2A C7 F1A 112.1(7)
F2A C7 F3A 98.2(6)
F1A C7 F3A 103.7(6)
F2A C7 C3 114.0(4)
F1A C7 C3 113.6(5)
F3A C7 C3 113.8(4)
C8 N3 C9 125.4(4)
C8 N3 H3N 110(3)
C9 N3 H3N 122(3)
N2 N1 C1 116.5(3)
N2 N1 H1N 108(3)
C1 N1 H1N 112(3)
C8 N2 N1 119.4(4)
C8 N2 H2N 116(3)
N1 N2 H2N 118(4)
C4 C3 C2 121.6(4)
C4 C3 C7 118.4(4)
C2 C3 C7 120.0(4)
N3 C8 N2 116.1(4)
N3 C8 S1 124.1(3)
N2 C8 S1 119.7(3)
C2 C1 C6 119.2(4)
C2 C1 N1 123.6(4)
C6 C1 N1 117.1(4)
C3 C2 C1 119.2(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C13 C10 C11 122.6(5)
C13 C10 C9 123.1(4)
C11 C10 C9 114.3(4)
N3 C9 C10 114.6(4)
N3 C9 H9A 108.6
C10 C9 H9A 108.6
N3 C9 H9B 108.6
C10 C9 H9B 108.6
H9A C9 H9B 107.6
C5 C6 C1 120.3(4)
C5 C6 H6 119.8
C1 C6 H6 119.8
C5 C4 C3 119.0(4)
C5 C4 H4 120.5
C3 C4 H4 120.5
C6 C5 C4 120.8(4)
C6 C5 H5 119.6
C4 C5 H5 119.6
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C13 H13A 120.0
C10 C13 H13B 120.0
H13A C13 H13B 120.0
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 C7 F1 F2 -110.7(18)
C1 N1 N2 C8 133.5(4)
F2A C7 C3 C4 -60.3(7)
F1A C7 C3 C4 69.8(7)
F3A C7 C3 C4 -171.8(6)
F2A C7 C3 C2 119.7(6)
F1A C7 C3 C2 -110.2(7)
F3A C7 C3 C2 8.1(7)
C9 N3 C8 N2 168.5(4)
C9 N3 C8 S1 -13.7(6)
N1 N2 C8 N3 -12.9(5)
N1 N2 C8 S1 169.2(3)
N2 N1 C1 C2 -9.8(6)
N2 N1 C1 C6 172.2(4)
C4 C3 C2 C1 -0.2(6)
C7 C3 C2 C1 179.8(4)
C6 C1 C2 C3 -0.5(6)
N1 C1 C2 C3 -178.5(4)
C8 N3 C9 C10 -91.7(5)
C13 C10 C9 N3 -0.6(7)
C11 C10 C9 N3 179.9(4)
C2 C1 C6 C5 0.8(6)
N1 C1 C6 C5 178.9(4)
C2 C3 C4 C5 0.7(6)
C7 C3 C4 C5 -179.3(4)
C1 C6 C5 C4 -0.3(6)
C3 C4 C5 C6 -0.4(6)
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
N2 H2N S1 3_656 0.70(5) 2.69(5) 3.366(5) 162(5) yes
N1 H1N S1 1_565 0.77(5) 2.62(5) 3.375(4) 167(4) yes