 
data_2008lsh057
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
N-(2-fluorophenyl)acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H8 F N O'
_chemical_formula_weight          153.15
 
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                    10.5132(4)
_cell_length_b                    9.4393(3)
_cell_length_c                    15.1635(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1504.78(9)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     14699
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut block'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.80
_exptl_crystal_size_mid           0.60
_exptl_crystal_size_min           0.50
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              640
_exptl_absorpt_coefficient_mu     0.107
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9195
_exptl_absorpt_correction_T_max   0.9486
_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 0.6183 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             12216
_diffrn_reflns_av_R_equivalents   0.0359
_diffrn_reflns_av_sigmaI/netI     0.0236
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1716
_reflns_number_gt                 1482
_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 hydrogen atoms was located on the difference map and subsequently 
restrained as follows:
DFIX 0.88 0.02 N1 H1N 

Furthermore the ADPs of the disordered phenyl ring were restrained:
EADP C1A C1B
EADP C2A C2B
EADP C4A C3B
EADP C4A C4B
EADP C5A C5B
EADP C6A C6B
;
 
_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)+(0.0538P)²+0.5424P] 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          1716
_refine_ls_number_parameters      133
_refine_ls_number_restraints      16
_refine_ls_R_factor_all           0.0474
_refine_ls_R_factor_gt            0.0394
_refine_ls_wR_factor_ref          0.1056
_refine_ls_wR_factor_gt           0.1005
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.041
_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
C7 C 0.24428(12) -0.10002(12) 0.59531(8) 0.0226(3) Uani 1 1 d . A .
C8 C 0.37767(12) -0.05554(13) 0.57257(10) 0.0311(3) Uani 1 1 d . . .
H8A H 0.4382 -0.1089 0.6088 0.047 Uiso 1 1 calc R . .
H8B H 0.3878 0.0460 0.5840 0.047 Uiso 1 1 calc R . .
H8C H 0.3940 -0.0747 0.5101 0.047 Uiso 1 1 calc R . .
N1 N 0.16140(9) 0.00652(10) 0.60908(7) 0.0201(2) Uani 1 1 d D . .
O1 O 0.21366(9) -0.22552(9) 0.59928(8) 0.0380(3) Uani 1 1 d . . .
C1A C 0.0278(3) -0.0104(7) 0.6284(5) 0.0171(5) Uani 0.822(2) 1 d PD A 1
C2A C -0.0299(2) 0.0857(4) 0.6842(3) 0.0209(5) Uani 0.822(2) 1 d PD A 1
C3A C -0.15841(17) 0.0828(3) 0.7039(2) 0.0255(5) Uani 0.822(2) 1 d PD A 1
H3A H -0.1954 0.1516 0.7417 0.031 Uiso 0.822(2) 1 calc PR A 1
C4A C -0.2317(3) -0.0241(4) 0.6665(3) 0.0293(6) Uani 0.822(2) 1 d PD A 1
H4A H -0.3201 -0.0299 0.6791 0.035 Uiso 0.822(2) 1 calc PR A 1
C5A C -0.1755(4) -0.1219(5) 0.6108(4) 0.0293(6) Uani 0.822(2) 1 d PD A 1
H5A H -0.2264 -0.1944 0.5854 0.035 Uiso 0.822(2) 1 calc PR A 1
C6A C -0.0476(3) -0.1169(3) 0.5911(2) 0.0214(5) Uani 0.822(2) 1 d PD A 1
H6A H -0.0110 -0.1851 0.5527 0.026 Uiso 0.822(2) 1 calc PR A 1
F1A F 0.04482(9) 0.19043(9) 0.71963(6) 0.0322(3) Uani 0.822(2) 1 d PD A 1
C1B C 0.0466(19) -0.003(3) 0.629(2) 0.0171(5) Uani 0.178(2) 1 d PD A 2
C2B C -0.0366(16) -0.0921(17) 0.5932(13) 0.0209(5) Uani 0.178(2) 1 d PD A 2
C3B C -0.170(2) -0.105(3) 0.613(2) 0.0293(6) Uani 0.178(2) 1 d PD A 2
H3B H -0.2235 -0.1758 0.5886 0.035 Uiso 0.178(2) 1 calc PR A 2
C4B C -0.2138(17) -0.002(2) 0.6734(17) 0.0293(6) Uani 0.178(2) 1 d PD A 2
H4B H -0.3006 -0.0005 0.6908 0.035 Uiso 0.178(2) 1 calc PR A 2
C5B C -0.1316(15) 0.095(2) 0.7064(13) 0.0293(6) Uani 0.178(2) 1 d PD A 2
H5B H -0.1640 0.1636 0.7465 0.035 Uiso 0.178(2) 1 calc PR A 2
C6B C -0.0092(16) 0.101(2) 0.6865(15) 0.0214(5) Uani 0.178(2) 1 d PD A 2
H6B H 0.0421 0.1740 0.7104 0.026 Uiso 0.178(2) 1 calc PR A 2
F1B F 0.0035(4) -0.1882(4) 0.5291(3) 0.0307(13) Uani 0.178(2) 1 d PD A 2
H1N H 0.1915(14) 0.0931(14) 0.6068(10) 0.034(4) 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
C7 0.0243(6) 0.0149(5) 0.0287(6) 0.0000(4) 0.0040(5) 0.0008(4)
C8 0.0239(6) 0.0219(6) 0.0474(8) -0.0003(6) 0.0094(5) 0.0002(5)
N1 0.0203(5) 0.0115(4) 0.0284(5) -0.0005(4) 0.0005(4) -0.0004(4)
O1 0.0277(5) 0.0126(4) 0.0738(7) 0.0016(4) 0.0092(5) 0.0020(3)
C1A 0.0156(14) 0.0156(10) 0.0201(5) 0.0027(6) -0.0002(13) -0.0001(12)
C2A 0.0214(14) 0.0153(12) 0.0258(8) -0.0003(8) -0.0001(10) -0.0016(9)
C3A 0.0187(12) 0.0276(11) 0.0304(8) 0.0002(8) 0.0073(10) 0.0046(11)
C4A 0.0183(12) 0.0348(17) 0.0350(11) 0.0031(10) 0.0020(10) -0.0029(9)
C5A 0.0271(9) 0.0289(15) 0.0320(9) -0.0003(10) -0.0031(7) -0.0087(9)
C6A 0.0241(9) 0.0162(13) 0.0238(7) -0.0028(9) -0.0008(7) -0.0054(8)
F1A 0.0319(5) 0.0240(5) 0.0408(6) -0.0150(4) 0.0022(4) -0.0010(4)
C1B 0.0156(14) 0.0156(10) 0.0201(5) 0.0027(6) -0.0002(13) -0.0001(12)
C2B 0.0214(14) 0.0153(12) 0.0258(8) -0.0003(8) -0.0001(10) -0.0016(9)
C3B 0.0183(12) 0.0348(17) 0.0350(11) 0.0031(10) 0.0020(10) -0.0029(9)
C4B 0.0183(12) 0.0348(17) 0.0350(11) 0.0031(10) 0.0020(10) -0.0029(9)
C5B 0.0271(9) 0.0289(15) 0.0320(9) -0.0003(10) -0.0031(7) -0.0087(9)
C6B 0.0241(9) 0.0162(13) 0.0238(7) -0.0028(9) -0.0008(7) -0.0054(8)
F1B 0.038(2) 0.024(2) 0.030(2) -0.0072(17) -0.0004(18) -0.0045(18)
 
_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
C7 O1 1.2291(14) . ?
C7 N1 1.3469(14) . ?
C7 C8 1.5040(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 C1B 1.25(2) . ?
N1 C1A 1.444(3) . ?
N1 H1N 0.877(13) . ?
C1A C2A 1.380(4) . ?
C1A C6A 1.399(4) . ?
C2A F1A 1.372(3) . ?
C2A C3A 1.384(2) . ?
C3A C4A 1.390(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.377(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1B C2B 1.332(17) . ?
C1B C6B 1.432(19) . ?
C2B F1B 1.396(14) . ?
C2B C3B 1.443(17) . ?
C3B C4B 1.409(18) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.355(15) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.323(14) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
 
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
O1 C7 N1 122.86(11) . . ?
O1 C7 C8 121.64(11) . . ?
N1 C7 C8 115.49(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1B N1 C7 127.7(15) . . ?
C1B N1 C1A 3.4(13) . . ?
C7 N1 C1A 125.3(3) . . ?
C1B N1 H1N 115.1(18) . . ?
C7 N1 H1N 117.1(10) . . ?
C1A N1 H1N 117.5(10) . . ?
C2A C1A C6A 118.1(2) . . ?
C2A C1A N1 118.6(3) . . ?
C6A C1A N1 123.3(4) . . ?
F1A C2A C1A 117.5(2) . . ?
F1A C2A C3A 119.2(3) . . ?
C1A C2A C3A 123.2(2) . . ?
C2A C3A C4A 117.9(3) . . ?
C2A C3A H3A 121.1 . . ?
C4A C3A H3A 121.1 . . ?
C5A C4A C3A 119.7(3) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C6A C5A C4A 121.7(3) . . ?
C6A C5A H5A 119.1 . . ?
C4A C5A H5A 119.1 . . ?
C5A C6A C1A 119.3(3) . . ?
C5A C6A H6A 120.3 . . ?
C1A C6A H6A 120.3 . . ?
N1 C1B C2B 125(2) . . ?
N1 C1B C6B 119.8(17) . . ?
C2B C1B C6B 114.2(14) . . ?
C1B C2B F1B 119.9(15) . . ?
C1B C2B C3B 127.3(15) . . ?
F1B C2B C3B 112.8(14) . . ?
C4B C3B C2B 113.3(15) . . ?
C4B C3B H3B 123.4 . . ?
C2B C3B H3B 123.4 . . ?
C5B C4B C3B 119.9(16) . . ?
C5B C4B H4B 120.1 . . ?
C3B C4B H4B 120.1 . . ?
C6B C5B C4B 124.2(17) . . ?
C6B C5B H5B 117.9 . . ?
C4B C5B H5B 117.9 . . ?
C5B C6B C1B 120.7(16) . . ?
C5B C6B H6B 119.6 . . ?
C1B C6B H6B 119.6 . . ?
 
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
N1 H1N O1  0.877(13) 1.984(13) 2.8540(13) 170.9(15) 8_665
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.244
_refine_diff_density_min   -0.221
_refine_diff_density_rms    0.040
