 
data_2008lsh001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
N-[4-(trifluoromethyl)phenyl]acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H8 F3 N O'
_chemical_formula_weight          203.16
 
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'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
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                    9.6630(3)
_cell_length_b                    9.2888(2)
_cell_length_c                    19.8221(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1779.19(8)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     13268
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.517
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              832
_exptl_absorpt_coefficient_mu     0.142
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9325
_exptl_absorpt_correction_T_max   0.9777
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
The transmission factors above were calculated using SHELXL
and are based on the crystal size. SADABS estimates the 
minimum and maximum transmission as 0.6277 and 0.7456, respectively.  
;
 
_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             18344
_diffrn_reflns_av_R_equivalents   0.0499
_diffrn_reflns_av_sigmaI/netI     0.0292
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.21
_diffrn_reflns_theta_max          27.50
_reflns_number_total              2036
_reflns_number_gt                 1543
_reflns_threshold_expression      >2sigma(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     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 2sigma(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.

The amide group was found to be disordered over two positions. The ADPs and 
the geometry of the minor component were restrained to be the same as in the 
major component. 
The amide hydrogen atoms for the two components could not be located on the 
difference map and were positioned geometrically and refined as riding on 
the atoms they are bonded to. 
;
 
_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)+(0.0480P)²+2.0386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2036
_refine_ls_number_parameters      142
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0728
_refine_ls_R_factor_gt            0.0551
_refine_ls_wR_factor_ref          0.1479
_refine_ls_wR_factor_gt           0.1389
_refine_ls_goodness_of_fit_ref    1.117
_refine_ls_restrained_S_all       1.116
_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
C1 C 0.7509(2) 0.3624(2) 0.65627(9) 0.0175(4) Uani 1 1 d . . .
C2 C 0.8756(2) 0.3199(2) 0.62738(11) 0.0240(5) Uani 1 1 d . A .
H2 H 0.9607 0.3540 0.6453 0.029 Uiso 1 1 calc R . .
C3 C 0.8755(2) 0.2274(2) 0.57209(11) 0.0234(5) Uani 1 1 d . . .
H3 H 0.9607 0.1990 0.5522 0.028 Uiso 1 1 calc R A .
C4 C 0.7516(2) 0.1766(2) 0.54582(9) 0.0195(4) Uani 1 1 d . A .
C5 C 0.6277(2) 0.2149(2) 0.57620(11) 0.0241(5) Uani 1 1 d . . .
H5 H 0.5430 0.1774 0.5594 0.029 Uiso 1 1 calc R A .
C6 C 0.6270(2) 0.3073(2) 0.63087(11) 0.0230(5) Uani 1 1 d . A .
H6 H 0.5416 0.3335 0.6513 0.028 Uiso 1 1 calc R . .
C9 C 0.7520(2) 0.0907(2) 0.48228(10) 0.0217(4) Uani 1 1 d . . .
C7A C 0.8430(2) 0.5185(3) 0.74793(12) 0.0209(5) Uani 0.830(3) 1 d PD A 1
C8A C 0.7950(3) 0.6206(3) 0.80248(15) 0.0285(6) Uani 0.830(3) 1 d PD A 1
H8A1 H 0.8356 0.5920 0.8458 0.043 Uiso 0.830(3) 1 calc PR A 1
H8A2 H 0.6939 0.6172 0.8057 0.043 Uiso 0.830(3) 1 calc PR A 1
H8A3 H 0.8244 0.7187 0.7913 0.043 Uiso 0.830(3) 1 calc PR A 1
N1A N 0.7390(4) 0.4600(7) 0.7099(3) 0.0182(8) Uani 0.830(3) 1 d PD A 1
H1A H 0.6544 0.4869 0.7205 0.022 Uiso 0.830(3) 1 calc PR A 1
O1A O 0.96597(19) 0.4908(2) 0.73896(9) 0.0290(5) Uani 0.830(3) 1 d PD A 1
C7B C 0.6581(11) 0.5196(12) 0.7483(6) 0.0209(5) Uani 0.170(3) 1 d PD A 2
C8B C 0.7078(15) 0.6267(16) 0.8012(7) 0.0285(6) Uani 0.170(3) 1 d PD A 2
H8B1 H 0.8091 0.6242 0.8036 0.043 Uiso 0.170(3) 1 calc PR A 2
H8B2 H 0.6689 0.6010 0.8452 0.043 Uiso 0.170(3) 1 calc PR A 2
H8B3 H 0.6774 0.7237 0.7887 0.043 Uiso 0.170(3) 1 calc PR A 2
N1B N 0.765(3) 0.462(4) 0.7124(16) 0.0182(8) Uani 0.170(3) 1 d PD A 2
H1BN H 0.8496 0.4879 0.7241 0.022 Uiso 0.170(3) 1 calc PR A 2
O1B O 0.5354(9) 0.4916(11) 0.7395(5) 0.0290(5) Uani 0.170(3) 1 d PD A 2
F1 F 0.76215(19) 0.17501(16) 0.42735(6) 0.0476(5) Uani 1 1 d . A .
F2 F 0.63834(15) 0.01289(17) 0.47327(7) 0.0436(4) Uani 1 1 d . A .
F3 F 0.85848(15) -0.00041(16) 0.47798(7) 0.0435(4) Uani 1 1 d . A .
 
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
C1 0.0164(9) 0.0184(9) 0.0177(8) 0.0028(7) 0.0003(8) -0.0005(7)
C2 0.0166(10) 0.0291(11) 0.0264(10) -0.0032(9) -0.0003(8) -0.0018(8)
C3 0.0175(10) 0.0275(11) 0.0253(11) -0.0016(8) 0.0018(8) 0.0028(8)
C4 0.0220(9) 0.0166(9) 0.0201(9) 0.0023(7) 0.0007(8) 0.0011(8)
C5 0.0178(10) 0.0271(11) 0.0274(11) -0.0017(9) -0.0023(8) -0.0017(8)
C6 0.0137(10) 0.0295(11) 0.0260(10) -0.0029(9) 0.0010(8) -0.0013(8)
C9 0.0216(9) 0.0204(10) 0.0232(10) 0.0016(8) 0.0000(9) -0.0015(8)
C7A 0.0207(11) 0.0232(11) 0.0187(10) 0.0025(9) -0.0030(9) -0.0012(9)
C8A 0.0272(14) 0.0331(13) 0.0250(12) -0.0054(10) -0.0017(12) 0.0018(12)
N1A 0.011(2) 0.0230(9) 0.0202(10) -0.0010(7) -0.0008(15) -0.0001(17)
O1A 0.0132(9) 0.0410(10) 0.0327(10) -0.0053(8) -0.0053(8) 0.0018(8)
C7B 0.0207(11) 0.0232(11) 0.0187(10) 0.0025(9) -0.0030(9) -0.0012(9)
C8B 0.0272(14) 0.0331(13) 0.0250(12) -0.0054(10) -0.0017(12) 0.0018(12)
N1B 0.011(2) 0.0230(9) 0.0202(10) -0.0010(7) -0.0008(15) -0.0001(17)
O1B 0.0132(9) 0.0410(10) 0.0327(10) -0.0053(8) -0.0053(8) 0.0018(8)
F1 0.0927(13) 0.0306(8) 0.0196(6) 0.0030(5) 0.0006(7) -0.0017(8)
F2 0.0368(8) 0.0511(9) 0.0429(8) -0.0224(7) 0.0066(6) -0.0171(7)
F3 0.0405(8) 0.0479(9) 0.0422(8) -0.0199(7) -0.0108(7) 0.0238(7)
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
C1 C2 1.392(3) . ?
C1 C6 1.396(3) . ?
C1 N1A 1.403(5) . ?
C1 N1B 1.46(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 C9 1.491(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 F2 1.326(2) . ?
C9 F3 1.335(2) . ?
C9 F1 1.345(2) . ?
C7A O1A 1.228(3) . ?
C7A N1A 1.368(5) . ?
C7A C8A 1.511(3) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
N1A H1A 0.8800 . ?
C7B O1B 1.226(12) . ?
C7B N1B 1.364(16) . ?
C7B C8B 1.523(13) . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
N1B H1BN 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
C2 C1 C6 119.39(18) . . ?
C2 C1 N1A 124.5(2) . . ?
C6 C1 N1A 116.1(2) . . ?
C2 C1 N1B 114.4(10) . . ?
C6 C1 N1B 126.2(10) . . ?
N1A C1 N1B 10.2(10) . . ?
C1 C2 C3 119.87(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.36(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.64(18) . . ?
C5 C4 C9 120.42(19) . . ?
C3 C4 C9 119.78(18) . . ?
C6 C5 C4 120.29(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.37(19) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
F2 C9 F3 106.53(17) . . ?
F2 C9 F1 105.60(17) . . ?
F3 C9 F1 105.14(17) . . ?
F2 C9 C4 113.77(17) . . ?
F3 C9 C4 113.27(17) . . ?
F1 C9 C4 111.84(17) . . ?
O1A C7A N1A 123.2(3) . . ?
O1A C7A C8A 122.1(2) . . ?
N1A C7A C8A 114.7(2) . . ?
C7A N1A C1 127.9(3) . . ?
C7A N1A H1A 116.1 . . ?
C1 N1A H1A 116.1 . . ?
O1B C7B N1B 125.3(16) . . ?
O1B C7B C8B 122.8(11) . . ?
N1B C7B C8B 112.0(15) . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C7B N1B C1 125(2) . . ?
C7B N1B H1BN 117.5 . . ?
C1 N1B H1BN 117.5 . . ?
 
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
N1A H1A O1A  0.88 1.99 2.841(4) 161.9 6_557
N1B H1BN O1B  0.88 1.94 2.79(3) 164.2 6_657
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.307
_refine_diff_density_min   -0.285
_refine_diff_density_rms    0.054
