 
data_2008lsh092
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 N-(4-nitrophenyl)acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H8 N2 O3'
_chemical_formula_weight          180.16
 
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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    3.821(5)
_cell_length_b                    9.726(14)
_cell_length_c                    22.67(3)
_cell_angle_alpha                 92.151(16)
_cell_angle_beta                  93.359(18)
_cell_angle_gamma                 100.409(16)
_cell_volume                      826.2(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     819
_cell_measurement_theta_min       3.25
_cell_measurement_theta_max       27.90
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.448
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              376
_exptl_absorpt_coefficient_mu     0.113
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
No absorption correction was applied to the data. Since the
data was provided by a service and did not contain any 
direction cosines an absorption correction could not be 
applied retrospectively. 
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          'Diamond beamline I19'
_diffrn_radiation_monochromator   'silicon double crystal'
_diffrn_measurement_device_type   
'Rigaku Saturn 724+ detector on Crystal Logics diffractometer'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             5984
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.1047
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_theta_min          0.87
_diffrn_reflns_theta_max          24.20
_reflns_number_total              5990
_reflns_number_gt                 4248
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Rigaku CrystalClear'
_computing_cell_refinement        'Bruker Apex2'
_computing_data_reduction         'Bruker Apex2'
_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 were positioned geometrically and refined as riding
on the atoms they are bonded to. 

The structure refines with untypically high R-factors, indicating that there
might be twinning present. In fact the sample was found badly twinned in 
the home laboratory hence it was sent to the synchrotron. Unfortunately the 
raw data is not accessible and hence no appropriate processing of the data 
could take place. A hklf5 file was generated using the MAKE HKLF5 program 
available in WinGX and used in the final refinement. The BASF refined to 
0.23183. This is far from the ideal treatment, but nevertheless the R-factor 
dropped by 5% and the connectivity of the structure is unambiguously 
determined.  
The original data contained 5987 total reflections, which merged to 2807
unique reflections (Rmerg=0.0631), of which 2048 were observed. 
;
 
_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)+(0.0401P)²+12.2011P] 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        0.051(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5990
_refine_ls_number_parameters      239
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1847
_refine_ls_R_factor_gt            0.1566
_refine_ls_wR_factor_ref          0.3795
_refine_ls_wR_factor_gt           0.3672
_refine_ls_goodness_of_fit_ref    1.129
_refine_ls_restrained_S_all       1.129
_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 -0.423(2) 0.7080(7) -0.3434(3) 0.0299(18) Uani 1 1 d . . .
C2 C -0.444(2) 0.8383(8) -0.3698(3) 0.0349(19) Uani 1 1 d . . .
H2 H -0.5078 0.9128 -0.3471 0.042 Uiso 1 1 calc R . .
C3 C -0.371(2) 0.8552(8) -0.4277(3) 0.039(2) Uani 1 1 d . . .
H3 H -0.3921 0.9405 -0.4455 0.047 Uiso 1 1 calc R . .
C4 C -0.265(2) 0.7467(8) -0.4611(3) 0.0325(18) Uani 1 1 d . . .
C5 C -0.243(2) 0.6180(7) -0.4361(4) 0.037(2) Uani 1 1 d . . .
H5 H -0.1750 0.5444 -0.4590 0.044 Uiso 1 1 calc R . .
C6 C -0.321(2) 0.6000(7) -0.3778(3) 0.0328(19) Uani 1 1 d . . .
H6 H -0.3055 0.5135 -0.3606 0.039 Uiso 1 1 calc R . .
C7 C -0.603(2) 0.7670(8) -0.2417(3) 0.0344(19) Uani 1 1 d . . .
C8 C -0.677(3) 0.6992(9) -0.1824(3) 0.044(2) Uani 1 1 d . . .
H8A H -0.4663 0.7262 -0.1548 0.067 Uiso 1 1 calc R . .
H8B H -0.7293 0.5972 -0.1888 0.067 Uiso 1 1 calc R . .
H8C H -0.8812 0.7311 -0.1659 0.067 Uiso 1 1 calc R . .
N1 N -0.5033(18) 0.6818(6) -0.2848(3) 0.0353(16) Uani 1 1 d . . .
H1 H -0.4873 0.5971 -0.2740 0.042 Uiso 1 1 calc R . .
N2 N -0.1727(18) 0.7687(6) -0.5235(3) 0.0374(17) Uani 1 1 d . . .
O1 O -0.6234(15) 0.8915(5) -0.2499(2) 0.0397(14) Uani 1 1 d . . .
O2 O -0.2355(17) 0.8749(5) -0.5467(2) 0.0432(15) Uani 1 1 d . . .
O3 O -0.0451(17) 0.6748(6) -0.5490(2) 0.0458(16) Uani 1 1 d . . .
C11 C -0.157(2) 0.2081(8) -0.1598(3) 0.0334(18) Uani 1 1 d . . .
C12 C -0.115(2) 0.3391(8) -0.1284(3) 0.0353(19) Uani 1 1 d . . .
H12 H -0.1940 0.4161 -0.1461 0.042 Uiso 1 1 calc R . .
C13 C 0.047(2) 0.3534(7) -0.0704(3) 0.0305(18) Uani 1 1 d . . .
H13 H 0.0820 0.4405 -0.0484 0.037 Uiso 1 1 calc R . .
C14 C 0.152(2) 0.2378(7) -0.0461(3) 0.0338(19) Uani 1 1 d . . .
C15 C 0.107(2) 0.1109(7) -0.0764(3) 0.0331(19) Uani 1 1 d . . .
H15 H 0.1822 0.0335 -0.0585 0.040 Uiso 1 1 calc R . .
C16 C -0.049(2) 0.0966(8) -0.1329(3) 0.036(2) Uani 1 1 d . . .
H16 H -0.0824 0.0083 -0.1539 0.043 Uiso 1 1 calc R . .
C17 C -0.421(2) 0.2792(7) -0.2556(3) 0.0298(17) Uani 1 1 d . . .
C18 C -0.614(2) 0.2151(8) -0.3147(3) 0.038(2) Uani 1 1 d . . .
H18A H -0.8001 0.2677 -0.3265 0.057 Uiso 1 1 calc R . .
H18B H -0.7216 0.1172 -0.3098 0.057 Uiso 1 1 calc R . .
H18C H -0.4414 0.2197 -0.3453 0.057 Uiso 1 1 calc R . .
N11 N -0.3376(18) 0.1874(6) -0.2176(3) 0.0361(17) Uani 1 1 d . . .
H11 H -0.4043 0.0992 -0.2300 0.043 Uiso 1 1 calc R . .
N12 N 0.317(2) 0.2553(8) 0.0157(3) 0.0430(18) Uani 1 1 d . . .
O11 O -0.3525(16) 0.4106(5) -0.2456(2) 0.0434(16) Uani 1 1 d . . .
O12 O 0.3098(18) 0.3643(6) 0.0446(2) 0.0529(18) Uani 1 1 d . . .
O13 O 0.4437(16) 0.1587(6) 0.0356(2) 0.0437(15) Uani 1 1 d . . .
 
 
_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 N1 1.402(10) . ?
C1 C6 1.409(10) . ?
C1 C2 1.434(10) . ?
C2 C3 1.367(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(10) . ?
C4 N2 1.492(10) . ?
C5 C6 1.383(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.247(9) . ?
C7 N1 1.373(10) . ?
C7 C8 1.536(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 H1 0.8800 . ?
N2 O2 1.232(8) . ?
N2 O3 1.249(8) . ?
C11 C16 1.379(10) . ?
C11 C12 1.415(10) . ?
C11 N11 1.434(9) . ?
C12 C13 1.411(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(10) . ?
C14 N12 1.492(9) . ?
C15 C16 1.372(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O11 1.266(9) . ?
C17 N11 1.331(9) . ?
C17 C18 1.542(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N11 H11 0.8800 . ?
N12 O13 1.221(9) . ?
N12 O12 1.230(9) . ?
 
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
N1 C1 C6 118.0(6) . . ?
N1 C1 C2 123.2(7) . . ?
C6 C1 C2 118.9(7) . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.2(7) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 N2 119.6(7) . . ?
C3 C4 N2 119.6(7) . . ?
C6 C5 C4 119.1(7) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.0(7) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 N1 122.0(8) . . ?
O1 C7 C8 122.8(7) . . ?
N1 C7 C8 115.3(7) . . ?
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 . . ?
C7 N1 C1 130.4(6) . . ?
C7 N1 H1 114.8 . . ?
C1 N1 H1 114.8 . . ?
O2 N2 O3 124.6(7) . . ?
O2 N2 C4 118.5(6) . . ?
O3 N2 C4 116.9(6) . . ?
C16 C11 C12 119.7(7) . . ?
C16 C11 N11 119.7(6) . . ?
C12 C11 N11 120.4(7) . . ?
C13 C12 C11 118.8(7) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 118.6(7) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 122.4(7) . . ?
C15 C14 N12 120.2(7) . . ?
C13 C14 N12 117.4(7) . . ?
C14 C15 C16 119.3(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 121.2(7) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
O11 C17 N11 124.1(6) . . ?
O11 C17 C18 120.7(6) . . ?
N11 C17 C18 115.3(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N11 C11 130.8(6) . . ?
C17 N11 H11 114.6 . . ?
C11 N11 H11 114.6 . . ?
O13 N12 O12 123.2(6) . . ?
O13 N12 C14 118.1(7) . . ?
O12 N12 C14 118.6(7) . . ?
 
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 H1 O11  0.88 2.09 2.958(9) 169.8 .
N11 H11 O1  0.88 2.06 2.936(9) 171.0 1_545
 
_diffrn_measured_fraction_theta_max    0.953
_diffrn_reflns_theta_full              24.20
_diffrn_measured_fraction_theta_full   0.953
_refine_diff_density_max    0.575
_refine_diff_density_min   -0.545
_refine_diff_density_rms    0.143
