 
data_2011ilk0011b
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             
'1,3-bis(trifluoromethyl-phenyl)thiourea TMA OAc H2O'
_chemical_melting_point           ?
_chemical_formula_moiety          
'C15 H10 F6 N2 S, C4 H12 N, C2 H3 O2, H2 O'
_chemical_formula_sum
 'C21 H27 F6 N3 O3 S'
_chemical_formula_weight          515.52
 
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'
 'F'  'F'   0.0171   0.0103
 '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'
 
_symmetry_cell_setting            'Orthorhombic'
_symmetry_space_group_name_H-M    'Pbca'
_symmetry_space_group_name_Hall    '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    18.0324(8)
_cell_length_b                    14.0781(5)
_cell_length_c                    18.8217(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      4778.1(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     86059
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'fragment'
_exptl_crystal_colour             'colourless'
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.433
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2144
_exptl_absorpt_coefficient_mu     0.210
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9320
_exptl_absorpt_correction_T_max   0.9592
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)' 

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat' 
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             33951
_diffrn_reflns_av_R_equivalents   0.0989
_diffrn_reflns_av_sigmaI/netI     0.0557
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.09
_diffrn_reflns_theta_max          25.03
_reflns_number_total              4204
_reflns_number_gt                 3152
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0419P)²+37.2641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4204
_refine_ls_number_parameters      321
_refine_ls_number_restraints      24
_refine_ls_R_factor_all           0.1394
_refine_ls_R_factor_gt            0.1105
_refine_ls_wR_factor_ref          0.2495
_refine_ls_wR_factor_gt           0.2344
_refine_ls_goodness_of_fit_ref    1.135
_refine_ls_restrained_S_all       1.142
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C18 C 0.8653(4) 0.3240(6) 0.0324(5) 0.057(2) Uani 1 1 d . . .
H18A H 0.8516 0.3077 -0.0165 0.085 Uiso 1 1 calc R . .
H18B H 0.8956 0.3818 0.0323 0.085 Uiso 1 1 calc R . .
H18C H 0.8203 0.3347 0.0605 0.085 Uiso 1 1 calc R . .
C19 C 0.8601(5) 0.1570(6) 0.0624(6) 0.068(3) Uani 1 1 d . . .
H19A H 0.8457 0.1435 0.0132 0.101 Uiso 1 1 calc R . .
H19B H 0.8156 0.1681 0.0911 0.101 Uiso 1 1 calc R . .
H19C H 0.8876 0.1027 0.0817 0.101 Uiso 1 1 calc R . .
C20 C 0.9312(5) 0.2688(9) 0.1355(5) 0.083(3) Uani 1 1 d . . .
H20A H 0.9612 0.2173 0.1555 0.125 Uiso 1 1 calc R . .
H20B H 0.8871 0.2785 0.1651 0.125 Uiso 1 1 calc R . .
H20C H 0.9605 0.3274 0.1344 0.125 Uiso 1 1 calc R . .
C21 C 0.9776(4) 0.2277(6) 0.0203(4) 0.0488(19) Uani 1 1 d . . .
H21A H 0.9634 0.2134 -0.0288 0.073 Uiso 1 1 calc R . .
H21B H 1.0054 0.1740 0.0400 0.073 Uiso 1 1 calc R . .
H21C H 1.0086 0.2848 0.0212 0.073 Uiso 1 1 calc R . .
N3 N 0.9087(2) 0.2442(3) 0.0642(3) 0.0259(11) Uani 1 1 d . . .
F1 F 0.9955(3) 0.9960(4) 0.1076(3) 0.0809(18) Uani 1 1 d . B .
F2 F 0.9181(2) 0.9595(3) 0.1884(2) 0.0477(11) Uani 1 1 d . B .
F3 F 1.0236(3) 1.0194(3) 0.2152(4) 0.0867(19) Uani 1 1 d . B .
O1 O 0.7256(3) 0.2801(3) 0.1581(2) 0.0333(10) Uani 1 1 d D . .
H2W H 0.731(4) 0.232(3) 0.184(3) 0.040 Uiso 1 1 d D . .
H1W H 0.736(4) 0.334(2) 0.174(3) 0.040 Uiso 1 1 d D . .
C1 C 1.1074(4) 0.5115(5) 0.1381(3) 0.0337(15) Uani 1 1 d D . .
C2 C 1.0876(3) 0.6806(4) 0.1733(3) 0.0297(14) Uani 1 1 d . . .
C3 C 1.0109(3) 0.6913(5) 0.1681(3) 0.0322(15) Uani 1 1 d . B .
H3 H 0.9803 0.6367 0.1637 0.039 Uiso 1 1 calc R . .
C4 C 0.9790(3) 0.7805(5) 0.1693(3) 0.0323(14) Uani 1 1 d . . .
H4 H 0.9267 0.7870 0.1656 0.039 Uiso 1 1 calc R B .
C5 C 1.0234(3) 0.8607(4) 0.1759(3) 0.0303(14) Uani 1 1 d . B .
C6 C 1.1000(3) 0.8516(5) 0.1826(3) 0.0309(14) Uani 1 1 d . . .
H6 H 1.1303 0.9063 0.1884 0.037 Uiso 1 1 calc R B .
C7 C 1.1316(3) 0.7616(4) 0.1807(3) 0.0293(14) Uani 1 1 d . B .
H7 H 1.1839 0.7551 0.1845 0.035 Uiso 1 1 calc R . .
C8 C 1.1564(3) 0.3497(4) 0.1211(3) 0.0287(14) Uani 1 1 d . . .
C9 C 1.1643(4) 0.3407(5) 0.0483(3) 0.0330(15) Uani 1 1 d . B .
H9 H 1.1657 0.3960 0.0194 0.040 Uiso 1 1 calc R . .
C10 C 1.1701(3) 0.2519(4) 0.0171(3) 0.0325(14) Uani 1 1 d . . .
H10 H 1.1745 0.2463 -0.0330 0.039 Uiso 1 1 calc R B .
C11 C 1.1694(3) 0.1715(4) 0.0592(3) 0.0280(13) Uani 1 1 d . A .
C12 C 1.1628(3) 0.1798(4) 0.1333(3) 0.0309(14) Uani 1 1 d . . .
H12 H 1.1631 0.1249 0.1626 0.037 Uiso 1 1 calc R B .
C13 C 1.1560(3) 0.2687(5) 0.1629(3) 0.0308(14) Uani 1 1 d . B .
H13 H 1.1509 0.2746 0.2130 0.037 Uiso 1 1 calc R . .
C14 C 0.9904(4) 0.9576(5) 0.1733(4) 0.0383(16) Uani 1 1 d . . .
C15 C 1.1757(3) 0.0764(4) 0.0275(3) 0.0323(14) Uani 1 1 d D . .
C16 C 0.2684(3) 0.5333(4) 0.2932(3) 0.0235(12) Uani 1 1 d . . .
C17 C 0.3248(4) 0.5398(4) 0.3532(3) 0.0329(14) Uani 1 1 d . . .
H17A H 0.3254 0.6046 0.3721 0.049 Uiso 1 1 calc R . .
H17B H 0.3741 0.5236 0.3350 0.049 Uiso 1 1 calc R . .
H17C H 0.3112 0.4953 0.3910 0.049 Uiso 1 1 calc R . .
N1 N 1.1247(3) 0.5927(4) 0.1746(3) 0.0306(12) Uani 1 1 d . B .
H1 H 1.1639 0.5895 0.2024 0.037 Uiso 1 1 calc R . .
N2 N 1.1540(3) 0.4388(4) 0.1550(3) 0.0310(12) Uani 1 1 d . B .
H2 H 1.1853 0.4484 0.1902 0.037 Uiso 1 1 calc R . .
O2 O 0.2418(2) 0.6101(3) 0.2699(2) 0.0312(10) Uani 1 1 d . . .
O3 O 0.2531(2) 0.4525(3) 0.2683(2) 0.0299(10) Uani 1 1 d . . .
F4A F 1.1670(5) 0.0035(5) 0.0733(4) 0.0619(11) Uani 0.591(5) 1 d PD A 1
F5A F 1.2471(4) 0.0421(5) 0.0326(5) 0.0619(11) Uani 0.591(5) 1 d PD A 1
F6A F 1.1720(5) 0.0741(5) -0.0448(4) 0.0619(11) Uani 0.591(5) 1 d PD A 1
F4B F 1.1254(7) 0.0125(7) 0.0448(7) 0.0619(11) Uani 0.409(5) 1 d PD A 2
F5B F 1.2325(7) 0.0633(8) -0.0147(7) 0.0619(11) Uani 0.409(5) 1 d PD A 2
F6B F 1.1136(6) 0.0566(7) -0.0115(6) 0.0619(11) Uani 0.409(5) 1 d PD A 2
S1A S 1.0360(6) 0.4987(6) 0.0805(5) 0.0338(17) Uani 0.81(4) 1 d PD B 1
S1B S 1.060(3) 0.521(2) 0.0612(18) 0.027(7) Uani 0.19(4) 1 d PD B 2
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C18 N3 1.494(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N3 1.508(9) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.444(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N3 1.510(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1 C14 1.353(8) . ?
F2 C14 1.334(7) . ?
F3 C14 1.317(8) . ?
O1 H2W 0.84(2) . ?
O1 H1W 0.84(2) . ?
C1 N2 1.361(8) . ?
C1 N1 1.371(8) . ?
C1 S1B 1.685(13) . ?
C1 S1A 1.692(7) . ?
C2 C3 1.394(9) . ?
C2 C7 1.397(9) . ?
C2 N1 1.406(8) . ?
C3 C4 1.381(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(9) . ?
C5 C14 1.489(9) . ?
C6 C7 1.389(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.383(9) . ?
C8 C13 1.386(9) . ?
C8 N2 1.409(8) . ?
C9 C10 1.384(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.405(9) . ?
C11 C15 1.470(9) . ?
C12 C13 1.375(9) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 F5B 1.310(9) . ?
C15 F4B 1.318(9) . ?
C15 F4A 1.349(8) . ?
C15 F6A 1.364(8) . ?
C15 F6B 1.368(9) . ?
C15 F5A 1.378(8) . ?
C16 O3 1.261(7) . ?
C16 O2 1.262(7) . ?
C16 C17 1.521(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 N3 C18 109.8(7) . . ?
C20 N3 C19 112.3(7) . . ?
C18 N3 C19 107.4(6) . . ?
C20 N3 C21 108.3(6) . . ?
C18 N3 C21 109.1(5) . . ?
C19 N3 C21 109.8(5) . . ?
H2W O1 H1W 120(7) . . ?
N2 C1 N1 111.6(5) . . ?
N2 C1 S1B 125.0(6) . . ?
N1 C1 S1B 118.7(10) . . ?
N2 C1 S1A 122.7(5) . . ?
N1 C1 S1A 125.7(5) . . ?
S1B C1 S1A 22.1(16) . . ?
C3 C2 C7 118.8(6) . . ?
C3 C2 N1 124.7(6) . . ?
C7 C2 N1 116.5(5) . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 C14 120.8(6) . . ?
C6 C5 C14 118.9(6) . . ?
C7 C6 C5 119.2(6) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C13 119.2(6) . . ?
C9 C8 N2 122.3(6) . . ?
C13 C8 N2 118.4(5) . . ?
C8 C9 C10 120.7(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.1(6) . . ?
C10 C11 C15 120.9(5) . . ?
C12 C11 C15 119.0(5) . . ?
C13 C12 C11 119.1(6) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 121.2(6) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
F3 C14 F2 107.7(6) . . ?
F3 C14 F1 104.7(6) . . ?
F2 C14 F1 104.6(5) . . ?
F3 C14 C5 113.8(6) . . ?
F2 C14 C5 113.7(6) . . ?
F1 C14 C5 111.6(6) . . ?
F5B C15 F4B 126.3(9) . . ?
F5B C15 F4A 111.8(8) . . ?
F4B C15 F4A 40.8(6) . . ?
F5B C15 F6A 55.1(7) . . ?
F4B C15 F6A 101.4(8) . . ?
F4A C15 F6A 127.9(7) . . ?
F5B C15 F6B 106.5(8) . . ?
F4B C15 F6B 55.3(8) . . ?
F4A C15 F6B 95.3(7) . . ?
F6A C15 F6B 54.5(6) . . ?
F5B C15 F5A 42.5(6) . . ?
F4B C15 F5A 112.7(8) . . ?
F4A C15 F5A 78.3(6) . . ?
F6A C15 F5A 96.1(6) . . ?
F6B C15 F5A 136.9(7) . . ?
F5B C15 C11 115.8(7) . . ?
F4B C15 C11 117.9(7) . . ?
F4A C15 C11 115.1(6) . . ?
F6A C15 C11 115.0(5) . . ?
F6B C15 C11 109.9(6) . . ?
F5A C15 C11 111.3(5) . . ?
O3 C16 O2 124.1(5) . . ?
O3 C16 C17 118.4(5) . . ?
O2 C16 C17 117.5(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C2 128.0(5) . . ?
C1 N1 H1 116.0 . . ?
C2 N1 H1 116.0 . . ?
C1 N2 C8 125.6(5) . . ?
C1 N2 H2 117.2 . . ?
C8 N2 H2 117.2 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1 H2W O2  0.84(2) 1.99(3) 2.812(6) 169(7) 3_645
O1 H1W O3  0.84(2) 2.01(3) 2.839(6) 167(7) 6_656
N1 H1 O2  0.88 1.92 2.780(6) 167.1 1_655
N2 H2 O3  0.88 1.91 2.790(6) 173.0 1_655
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.972
_refine_diff_density_min   -0.702
_refine_diff_density_rms    0.097

