 
data_2008lsh167
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 N-(4-acetylphenyl)acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H11 N O2'
_chemical_formula_weight          177.20
 
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            Orthorhombic
_symmetry_space_group_name_H-M    'P 21 21 21'
 
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'
 
_cell_length_a                    7.5138(5)
_cell_length_b                    9.3146(7)
_cell_length_c                    12.8999(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      902.84(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     18819
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut lath'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.304
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              376
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9837
_exptl_absorpt_correction_T_max   0.9927
_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 ratio of
minimum and maximum transmission as 0.608369.  
;
 
_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    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7434
_diffrn_reflns_av_R_equivalents   0.0638
_diffrn_reflns_av_sigmaI/netI     0.0684
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.48
_diffrn_reflns_theta_max          27.49
_reflns_number_total              1993
_reflns_number_gt                 1414
_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 precession images contain extensive diffuse scattering indicating major
disorder of the crystal structure. Refinement yielded the whole molecule 
disordered over two positions. The disorder is not an artefact of too
higher symmetry as it is detected in all subgroups of P2(1)2(1)2(1) and the
best fit statistically was achieved in the chosen space group. 
The geometry of the minor component was restrained to be the same as that of 
the major component. Furthermore a global DELU restraint was applied and the 
ADP of C6B was approximated to isotropic behaviour. The distance between C1A
and N1A was restrained to 1.4Å. The thermal ellipsoids of the minor 
component have their major axis elongated in the same direction causing a
large U3/U1 ratio for the average U(i,j) tensor. This indicates that the 
molecule is disordered further, but no sensible model could be found, hence
the position of the minor component should be interpreted as an average. The 
whole crystal structure can be understood as alternating layers that contain
molecules in inverted orientations with further slippage of the layers with
respect to each other. 

The amide hydrogen atoms 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. 
 
 
;
 
_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)+(0.0131P)²+0.4627P] 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      SHELXL
_refine_ls_extinction_coef        0.064(16)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    3(5)
_refine_ls_number_reflns          1993
_refine_ls_number_parameters      218
_refine_ls_number_restraints      97
_refine_ls_R_factor_all           0.1192
_refine_ls_R_factor_gt            0.0785
_refine_ls_wR_factor_ref          0.1537
_refine_ls_wR_factor_gt           0.1377
_refine_ls_goodness_of_fit_ref    1.162
_refine_ls_restrained_S_all       1.172
_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
C1A C 0.0587(6) 0.5751(5) -0.0809(2) 0.0342(15) Uani 0.570(6) 1 d PGDU A 1
C2A C 0.1532(9) 0.6901(5) -0.0398(3) 0.0337(16) Uani 0.570(6) 1 d PGDU A 1
H2A H 0.2094 0.7570 -0.0847 0.040 Uiso 0.570(6) 1 calc PR A 1
C3A C 0.1656(9) 0.7070(5) 0.0670(3) 0.0317(15) Uani 0.570(6) 1 d PGDU A 1
H3A H 0.2302 0.7856 0.0951 0.038 Uiso 0.570(6) 1 calc PR A 1
C4A C 0.0834(7) 0.6091(4) 0.1327(2) 0.0358(15) Uani 0.570(6) 1 d PGDU A 1
C5A C -0.0112(6) 0.4942(4) 0.0916(3) 0.0392(14) Uani 0.570(6) 1 d PGDU A 1
H5A H -0.0674 0.4272 0.1365 0.047 Uiso 0.570(6) 1 calc PR A 1
C6A C -0.0235(5) 0.4772(4) -0.0152(3) 0.0250(13) Uani 0.570(6) 1 d PGDU A 1
H6A H -0.0882 0.3986 -0.0433 0.030 Uiso 0.570(6) 1 calc PR A 1
C7A C 0.0657(17) 0.6491(11) -0.2686(5) 0.042(3) Uani 0.570(6) 1 d PDU A 1
C8A C 0.0174(11) 0.5893(7) -0.3730(5) 0.0460(17) Uani 0.570(6) 1 d PDU A 1
H8A1 H -0.0851 0.6418 -0.4008 0.069 Uiso 0.570(6) 1 calc PR A 1
H8A2 H -0.0129 0.4875 -0.3661 0.069 Uiso 0.570(6) 1 calc PR A 1
H8A3 H 0.1187 0.5998 -0.4203 0.069 Uiso 0.570(6) 1 calc PR A 1
C9A C 0.086(2) 0.6367(14) 0.2436(6) 0.060(3) Uani 0.570(6) 1 d PDU A 1
C10A C -0.0015(15) 0.5404(10) 0.3214(4) 0.059(2) Uani 0.570(6) 1 d PDU A 1
H10A H 0.0478 0.4434 0.3153 0.088 Uiso 0.570(6) 1 calc PR A 1
H10B H -0.1300 0.5375 0.3083 0.088 Uiso 0.570(6) 1 calc PR A 1
H10C H 0.0205 0.5773 0.3913 0.088 Uiso 0.570(6) 1 calc PR A 1
N1A N 0.0334(7) 0.5501(5) -0.1879(3) 0.0387(13) Uani 0.570(6) 1 d PDU A 1
H1A H -0.0063 0.4647 -0.2059 0.046 Uiso 0.570(6) 1 calc PR A 1
O1A O 0.1174(8) 0.7713(5) -0.2578(4) 0.0497(14) Uani 0.570(6) 1 d PDU A 1
O2A O 0.1958(9) 0.7263(6) 0.2779(4) 0.0548(17) Uani 0.570(6) 1 d PDU A 1
C1B C 0.0552(12) 0.5725(9) 0.0775(7) 0.079(3) Uani 0.430(6) 1 d PGDU A 2
C6B C -0.0241(11) 0.4749(7) 0.0104(8) 0.092(4) Uani 0.430(6) 1 d PGDU A 2
H6B H -0.0883 0.3953 0.0373 0.110 Uiso 0.430(6) 1 calc PR A 2
C5B C -0.0095(10) 0.4936(7) -0.0962(8) 0.076(3) Uani 0.430(6) 1 d PGDU A 2
H5B H -0.0637 0.4268 -0.1421 0.091 Uiso 0.430(6) 1 calc PR A 2
C4B C 0.0845(12) 0.6099(8) -0.1356(7) 0.080(3) Uani 0.430(6) 1 d PGDU A 2
C3B C 0.1638(15) 0.7076(9) -0.0685(9) 0.087(4) Uani 0.430(6) 1 d PGDU A 2
H3B H 0.2280 0.7871 -0.0955 0.105 Uiso 0.430(6) 1 calc PR A 2
C2B C 0.1492(14) 0.6889(9) 0.0380(8) 0.083(4) Uani 0.430(6) 1 d PGDU A 2
H2B H 0.2034 0.7556 0.0839 0.100 Uiso 0.430(6) 1 calc PR A 2
C7B C 0.084(2) 0.6363(15) 0.2703(12) 0.078(4) Uani 0.430(6) 1 d PDU A 2
C8B C 0.012(2) 0.5832(14) 0.3730(12) 0.096(4) Uani 0.430(6) 1 d PDU A 2
H8B1 H 0.0962 0.6068 0.4284 0.144 Uiso 0.430(6) 1 calc PR A 2
H8B2 H -0.0047 0.4790 0.3699 0.144 Uiso 0.430(6) 1 calc PR A 2
H8B3 H -0.1028 0.6296 0.3872 0.144 Uiso 0.430(6) 1 calc PR A 2
C9B C 0.092(3) 0.6289(18) -0.2457(12) 0.087(4) Uani 0.430(6) 1 d PDU A 2
C10B C 0.0052(15) 0.5392(11) -0.3259(12) 0.094(4) Uani 0.430(6) 1 d PDU A 2
H10D H 0.0581 0.5601 -0.3937 0.141 Uiso 0.430(6) 1 calc PR A 2
H10E H -0.1225 0.5607 -0.3279 0.141 Uiso 0.430(6) 1 calc PR A 2
H10F H 0.0226 0.4376 -0.3093 0.141 Uiso 0.430(6) 1 calc PR A 2
N1B N 0.0329(11) 0.5513(8) 0.1837(8) 0.083(3) Uani 0.430(6) 1 d PDU A 2
H1B H -0.0225 0.4712 0.2000 0.100 Uiso 0.430(6) 1 calc PR A 2
O1B O 0.1201(15) 0.7663(8) 0.2629(11) 0.110(4) Uani 0.430(6) 1 d PDU A 2
O2B O 0.1970(12) 0.7286(8) -0.2711(9) 0.092(3) Uani 0.430(6) 1 d PDU A 2
 
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
C1A 0.036(4) 0.021(3) 0.046(3) 0.003(2) 0.002(3) 0.001(3)
C2A 0.031(4) 0.021(3) 0.049(3) 0.001(3) 0.006(3) -0.002(3)
C3A 0.020(3) 0.025(4) 0.049(3) 0.004(3) -0.005(3) -0.002(3)
C4A 0.040(4) 0.028(3) 0.040(3) -0.003(2) 0.004(3) 0.002(3)
C5A 0.025(3) 0.029(3) 0.064(3) 0.008(2) 0.007(3) -0.007(2)
C6A 0.019(3) 0.012(2) 0.044(3) -0.0018(19) 0.003(2) -0.0032(19)
C7A 0.055(6) 0.028(4) 0.043(3) 0.013(3) -0.007(3) 0.009(4)
C8A 0.054(4) 0.036(3) 0.049(3) 0.001(3) 0.003(3) 0.008(3)
C9A 0.092(8) 0.048(6) 0.042(4) -0.008(3) 0.010(4) 0.006(5)
C10A 0.056(5) 0.080(6) 0.040(3) 0.005(3) 0.003(4) -0.005(5)
N1A 0.038(3) 0.027(3) 0.052(3) -0.001(2) -0.006(2) -0.004(2)
O1A 0.053(3) 0.030(3) 0.066(3) -0.001(2) -0.011(3) 0.005(3)
O2A 0.063(4) 0.046(4) 0.056(3) -0.006(3) -0.009(3) -0.001(3)
C1B 0.023(5) 0.036(5) 0.178(8) 0.001(6) 0.010(6) 0.013(4)
C6B 0.070(8) 0.059(7) 0.146(7) 0.014(6) -0.006(7) -0.007(6)
C5B 0.032(5) 0.034(5) 0.161(9) 0.030(5) 0.002(6) 0.012(4)
C4B 0.019(5) 0.030(5) 0.190(9) 0.017(7) 0.001(7) 0.003(4)
C3B 0.037(7) 0.031(5) 0.194(11) 0.010(7) 0.010(8) 0.003(5)
C2B 0.037(7) 0.027(5) 0.186(11) -0.020(8) 0.015(11) -0.002(5)
C7B 0.035(7) 0.031(6) 0.168(9) 0.029(7) -0.046(8) -0.018(5)
C8B 0.045(7) 0.045(6) 0.198(11) 0.015(8) 0.026(10) -0.004(5)
C9B 0.040(7) 0.028(6) 0.192(10) 0.027(8) -0.008(10) 0.011(5)
C10B 0.033(5) 0.043(6) 0.205(13) 0.028(7) -0.019(8) -0.008(5)
N1B 0.040(5) 0.025(4) 0.185(7) 0.000(5) 0.013(6) 0.009(4)
O1B 0.067(6) 0.025(4) 0.237(12) -0.002(5) 0.043(7) -0.011(5)
O2B 0.052(5) 0.027(4) 0.197(9) -0.003(5) 0.017(6) -0.012(4)
 
_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
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A N1A 1.412(5) . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A C9A 1.453(8) . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O1A 1.211(10) . ?
C7A N1A 1.412(9) . ?
C7A C8A 1.502(9) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A O2A 1.255(13) . ?
C9A C10A 1.497(12) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
N1A H1A 0.8800 . ?
C1B C6B 1.3900 . ?
C1B C2B 1.3900 . ?
C1B N1B 1.395(10) . ?
C6B C5B 1.3900 . ?
C6B H6B 0.9500 . ?
C5B C4B 1.3900 . ?
C5B H5B 0.9500 . ?
C4B C3B 1.3900 . ?
C4B C9B 1.431(15) . ?
C3B C2B 1.3900 . ?
C3B H3B 0.9500 . ?
C2B H2B 0.9500 . ?
C7B O1B 1.245(14) . ?
C7B N1B 1.421(14) . ?
C7B C8B 1.514(15) . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B O2B 1.262(15) . ?
C9B C10B 1.481(16) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
N1B H1B 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
C2A C1A C6A 120.0 . . ?
C2A C1A N1A 124.7(3) . . ?
C6A C1A N1A 115.3(3) . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A C9A 118.6(6) . . ?
C5A C4A C9A 121.2(6) . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
O1A C7A N1A 125.7(7) . . ?
O1A C7A C8A 122.0(7) . . ?
N1A C7A C8A 112.2(7) . . ?
O2A C9A C4A 118.2(9) . . ?
O2A C9A C10A 116.8(8) . . ?
C4A C9A C10A 123.2(9) . . ?
C7A N1A C1A 126.1(5) . . ?
C7A N1A H1A 116.9 . . ?
C1A N1A H1A 116.9 . . ?
C6B C1B C2B 120.0 . . ?
C6B C1B N1B 117.9(7) . . ?
C2B C1B N1B 122.1(7) . . ?
C1B C6B C5B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B C9B 121.4(8) . . ?
C5B C4B C9B 118.6(8) . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C2B C1B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
O1B C7B N1B 122.7(14) . . ?
O1B C7B C8B 117.6(13) . . ?
N1B C7B C8B 114.2(10) . . ?
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 . . ?
O2B C9B C4B 111.9(13) . . ?
O2B C9B C10B 120.6(13) . . ?
C4B C9B C10B 127.4(13) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C1B N1B C7B 131.4(9) . . ?
C1B N1B H1B 114.3 . . ?
C7B N1B H1B 114.3 . . ?
 
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 2.04 2.919(7) 175.3 3_544
N1B H1B O1B  0.88 2.10 2.974(12) 172.1 3_545
 
_diffrn_measured_fraction_theta_max    0.984
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.984
_refine_diff_density_max    0.135
_refine_diff_density_min   -0.151
_refine_diff_density_rms    0.036
