 
data_2008lsh161
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 N-(4-ethylphenyl)acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H13 N O'
_chemical_formula_weight          163.21
 
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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    Cc
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    4.5852(2)
_cell_length_b                    21.3953(10)
_cell_length_c                    9.4310(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.001(3)
_cell_angle_gamma                 90.00
_cell_volume                      925.20(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     14100
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut sheet'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.172
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              352
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9703
_exptl_absorpt_correction_T_max   0.9985
_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 0.6319 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             9522
_diffrn_reflns_av_R_equivalents   0.0406
_diffrn_reflns_av_sigmaI/netI     0.0330
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.81
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2019
_reflns_number_gt                 1833
_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 coordinates of N1B were restrained to be the 
same as those of N1A and the general geometry of the two disordered parts
were restrained to be the same. The amide hydrogen atoms could not be 
located on the difference map and were positioned geometrically and 
refined as riding on the atoms they are bonded to. 

The structure was refined as a racemic twin; the absolute structure cannot
be assigned unambiguously. Inverting the structure results in a negative BASF.
;
 
_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)+(0.0563P)²+0.1469P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    2.3(17)
_refine_ls_number_reflns          2019
_refine_ls_number_parameters      141
_refine_ls_number_restraints      8
_refine_ls_R_factor_all           0.0433
_refine_ls_R_factor_gt            0.0376
_refine_ls_wR_factor_ref          0.0970
_refine_ls_wR_factor_gt           0.0934
_refine_ls_goodness_of_fit_ref    1.061
_refine_ls_restrained_S_all       1.059
_refine_ls_shift/su_max           0.001
_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 0.1477(2) 0.09137(5) 0.60893(15) 0.0210(3) Uani 1 1 d . . .
C2 C 0.0456(3) 0.11603(7) 0.73639(14) 0.0276(3) Uani 1 1 d . A .
H2 H 0.1129 0.0997 0.8241 0.033 Uiso 1 1 calc R . .
C3 C -0.1548(3) 0.16457(7) 0.73451(16) 0.0308(3) Uani 1 1 d . . .
H3 H -0.2234 0.1808 0.8221 0.037 Uiso 1 1 calc R A .
C4 C -0.2585(3) 0.19017(6) 0.60916(17) 0.0285(3) Uani 1 1 d . A .
C5 C -0.1548(3) 0.16463(7) 0.48322(16) 0.0308(3) Uani 1 1 d . . .
H5 H -0.2230 0.1810 0.3956 0.037 Uiso 1 1 calc R A .
C6 C 0.0455(3) 0.11592(6) 0.48183(15) 0.0277(3) Uani 1 1 d . A .
H6 H 0.1124 0.0994 0.3942 0.033 Uiso 1 1 calc R . .
C7A C 0.4658(6) 0.00766(12) 0.7100(3) 0.0245(7) Uani 0.497(4) 1 d PD A 1
C8A C 0.6766(7) -0.04264(15) 0.6656(4) 0.0314(8) Uani 0.497(4) 1 d PD A 1
H8A1 H 0.8762 -0.0292 0.6869 0.047 Uiso 0.497(4) 1 calc PR A 1
H8A2 H 0.6574 -0.0502 0.5636 0.047 Uiso 0.497(4) 1 calc PR A 1
H8A3 H 0.6333 -0.0812 0.7176 0.047 Uiso 0.497(4) 1 calc PR A 1
N1A N 0.3531(2) 0.04203(5) 0.60915(13) 0.0228(2) Uani 0.497(4) 1 d PD A 1
H1A H 0.4185 0.0325 0.5241 0.027 Uiso 0.497(4) 1 calc PR A 1
O1A O 0.4044(5) 0.01588(16) 0.8360(3) 0.0347(7) Uani 0.497(4) 1 d PD A 1
C7B C 0.4656(6) 0.00771(12) 0.5080(3) 0.0253(8) Uani 0.503(4) 1 d PD A 2
C8B C 0.6783(7) -0.04225(14) 0.5525(4) 0.0328(8) Uani 0.503(4) 1 d PD A 2
H8B1 H 0.6179 -0.0825 0.5125 0.049 Uiso 0.503(4) 1 calc PR A 2
H8B2 H 0.6818 -0.0452 0.6562 0.049 Uiso 0.503(4) 1 calc PR A 2
H8B3 H 0.8735 -0.0316 0.5177 0.049 Uiso 0.503(4) 1 calc PR A 2
N1B N 0.3531(2) 0.04203(5) 0.60915(13) 0.0228(2) Uani 0.503(4) 1 d PD A 2
H1B H 0.4183 0.0325 0.6942 0.027 Uiso 0.503(4) 1 calc PR A 2
O1B O 0.4046(5) 0.01567(16) 0.3817(3) 0.0353(7) Uani 0.503(4) 1 d PD A 2
C9 C -0.4657(3) 0.24485(6) 0.6090(2) 0.0373(4) Uani 1 1 d . . .
H9A H -0.5926 0.2424 0.6937 0.045 Uiso 1 1 calc R A .
H9B H -0.5920 0.2424 0.5240 0.045 Uiso 1 1 calc R . .
C10 C -0.3065(4) 0.30742(6) 0.6092(2) 0.0389(4) Uani 1 1 d . A .
H10A H -0.1857 0.3107 0.6946 0.058 Uiso 1 1 calc R . .
H10B H -0.4492 0.3415 0.6081 0.058 Uiso 1 1 calc R . .
H10C H -0.1821 0.3103 0.5249 0.058 Uiso 1 1 calc R . .
 
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 0.0211(6) 0.0194(6) 0.0224(6) -0.0003(5) -0.0001(5) -0.0044(5)
C2 0.0311(7) 0.0304(8) 0.0214(7) 0.0016(5) 0.0024(6) 0.0011(5)
C3 0.0302(7) 0.0314(8) 0.0308(8) -0.0058(6) 0.0063(6) 0.0001(6)
C4 0.0217(7) 0.0226(6) 0.0413(8) -0.0003(6) 0.0010(6) -0.0030(5)
C5 0.0314(8) 0.0304(8) 0.0305(8) 0.0053(6) -0.0050(6) 0.0014(6)
C6 0.0313(8) 0.0297(7) 0.0220(7) -0.0004(5) -0.0007(6) 0.0017(5)
C7A 0.0277(15) 0.0218(14) 0.0241(15) 0.0053(10) -0.0012(11) -0.0062(10)
C8A 0.0340(18) 0.0245(15) 0.0358(19) 0.0040(12) -0.0055(13) 0.0020(11)
N1A 0.0257(5) 0.0238(5) 0.0191(5) -0.0002(5) 0.0005(4) 0.0002(4)
O1A 0.0491(15) 0.0334(15) 0.0216(12) 0.0087(12) 0.0034(10) 0.0035(10)
C7B 0.0301(16) 0.0225(14) 0.0234(15) -0.0049(10) 0.0022(11) -0.0060(10)
C8B 0.0369(18) 0.0249(15) 0.0365(19) -0.0021(12) 0.0059(13) 0.0040(12)
N1B 0.0257(5) 0.0238(5) 0.0191(5) -0.0002(5) 0.0005(4) 0.0002(4)
O1B 0.0488(15) 0.0350(15) 0.0221(12) -0.0088(12) -0.0016(10) 0.0040(10)
C9 0.0271(7) 0.0262(7) 0.0588(10) -0.0001(8) -0.0007(7) 0.0012(6)
C10 0.0379(9) 0.0233(7) 0.0556(9) 0.0006(8) 0.0005(8) 0.0020(6)
 
_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 C6 1.3902(19) . ?
C1 C2 1.3938(18) . ?
C1 N1A 1.4148(15) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C9 1.5070(19) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7A O1A 1.234(4) . ?
C7A N1A 1.308(3) . ?
C7A C8A 1.506(4) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
N1A H1A 0.8800 . ?
C7B O1B 1.236(4) . ?
C7B C8B 1.506(4) . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9 C10 1.5250(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
 
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
C6 C1 C2 119.16(11) . . ?
C6 C1 N1A 120.51(12) . . ?
C2 C1 N1A 120.33(12) . . ?
C3 C2 C1 119.68(12) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 122.27(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 117.08(12) . . ?
C3 C4 C9 121.58(14) . . ?
C5 C4 C9 121.30(15) . . ?
C6 C5 C4 121.92(13) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.89(12) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1A C7A N1A 122.0(3) . . ?
O1A C7A C8A 121.0(3) . . ?
N1A C7A C8A 117.0(2) . . ?
C7A N1A C1 133.10(16) . . ?
C7A N1A H1A 113.4 . . ?
C1 N1A H1A 113.4 . . ?
O1B C7B C8B 120.8(3) . . ?
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 . . ?
C4 C9 C10 112.31(13) . . ?
C4 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C4 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
 
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 2.06 2.868(4) 153.2 2_554
N1B H1B O1B  0.88 2.05 2.861(4) 153.3 2
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.141
_refine_diff_density_min   -0.165
_refine_diff_density_rms    0.037
