 
data_2008lsh060
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
N-(3-chlorophenyl)acetamide
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H8 Cl N O'
_chemical_formula_weight          169.60
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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                    4.76670(10)
_cell_length_b                    18.4984(4)
_cell_length_c                    18.6318(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1642.88(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     103490
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut fragment'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.371
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              704
_exptl_absorpt_coefficient_mu     0.403
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9095
_exptl_absorpt_correction_T_max   0.9608
_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 0.6434 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             61033
_diffrn_reflns_av_R_equivalents   0.0532
_diffrn_reflns_av_sigmaI/netI     0.0218
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        24
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.48
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3760
_reflns_number_gt                 3449
_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 were located on the difference map and subsequently 
restrained as follows:
DFIX 0.88 0.02 
;
 
_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)+(0.0495P)²+0.3236P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.02(5)
_refine_ls_number_reflns          3760
_refine_ls_number_parameters      209
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0401
_refine_ls_R_factor_gt            0.0349
_refine_ls_wR_factor_ref          0.0876
_refine_ls_wR_factor_gt           0.0843
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.069
_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 -0.2706(4) -0.32415(9) 1.32073(9) 0.0295(4) Uani 1 1 d . . .
C2 C -0.2955(4) -0.24950(9) 1.33233(9) 0.0302(4) Uani 1 1 d . . .
H2 H -0.4254 -0.2214 1.3055 0.036 Uiso 1 1 calc R . .
C3 C -0.1262(4) -0.21786(10) 1.38369(10) 0.0364(4) Uani 1 1 d . . .
C4 C 0.0668(4) -0.25616(13) 1.42363(10) 0.0448(5) Uani 1 1 d . . .
H4 H 0.1814 -0.2327 1.4583 0.054 Uiso 1 1 calc R . .
C5 C 0.0885(5) -0.33008(13) 1.41159(12) 0.0476(5) Uani 1 1 d . . .
H5 H 0.2196 -0.3578 1.4384 0.057 Uiso 1 1 calc R . .
C6 C -0.0789(4) -0.36386(11) 1.36092(10) 0.0396(4) Uani 1 1 d . . .
H6 H -0.0626 -0.4145 1.3536 0.047 Uiso 1 1 calc R . .
C7 C -0.5898(4) -0.33485(9) 1.21619(9) 0.0288(3) Uani 1 1 d . . .
C8 C -0.7613(4) -0.38914(10) 1.17495(10) 0.0370(4) Uani 1 1 d . . .
H8A H -0.9597 -0.3753 1.1767 0.056 Uiso 1 1 calc R . .
H8B H -0.7377 -0.4371 1.1964 0.056 Uiso 1 1 calc R . .
H8C H -0.6983 -0.3903 1.1249 0.056 Uiso 1 1 calc R . .
N1 N -0.4400(3) -0.36195(8) 1.27140(8) 0.0297(3) Uani 1 1 d D . .
O1 O -0.5872(3) -0.27067(6) 1.19859(7) 0.0401(3) Uani 1 1 d . . .
Cl1 Cl 0.19298(12) -0.00095(3) 0.96898(3) 0.04670(14) Uani 1 1 d . . .
H1N H -0.456(5) -0.4079(9) 1.2804(12) 0.044(6) Uiso 1 1 d D . .
C11 C -0.1984(3) -0.12663(8) 1.11138(8) 0.0243(3) Uani 1 1 d . . .
C12 C -0.1218(4) -0.06658(9) 1.07006(9) 0.0283(3) Uani 1 1 d . . .
H12 H -0.2107 -0.0211 1.0765 0.034 Uiso 1 1 calc R . .
C13 C 0.0887(4) -0.07581(9) 1.01931(9) 0.0300(4) Uani 1 1 d . . .
C14 C 0.2202(4) -0.14142(10) 1.00742(9) 0.0307(4) Uani 1 1 d . . .
H14 H 0.3614 -0.1462 0.9717 0.037 Uiso 1 1 calc R . .
C15 C 0.1402(4) -0.20000(9) 1.04902(9) 0.0301(4) Uani 1 1 d . . .
H15 H 0.2282 -0.2455 1.0420 0.036 Uiso 1 1 calc R . .
C16 C -0.0662(4) -0.19282(9) 1.10053(9) 0.0267(3) Uani 1 1 d . . .
H16 H -0.1184 -0.2334 1.1288 0.032 Uiso 1 1 calc R . .
C17 C -0.5191(3) -0.06593(9) 1.19756(9) 0.0282(3) Uani 1 1 d . . .
C18 C -0.7453(4) -0.08061(10) 1.25188(10) 0.0339(4) Uani 1 1 d . . .
H18A H -0.6705 -0.0731 1.3003 0.051 Uiso 1 1 calc R . .
H18B H -0.8099 -0.1307 1.2470 0.051 Uiso 1 1 calc R . .
H18C H -0.9029 -0.0476 1.2437 0.051 Uiso 1 1 calc R . .
N11 N -0.4121(3) -0.12462(7) 1.16384(7) 0.0251(3) Uani 1 1 d D . .
O11 O -0.4328(3) -0.00406(7) 1.18585(7) 0.0388(3) Uani 1 1 d . . .
Cl2 Cl -0.17004(13) -0.12507(3) 1.39959(3) 0.04930(15) Uani 1 1 d . . .
H11N H -0.478(4) -0.1660(8) 1.1770(10) 0.024(5) Uiso 1 1 d 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 C6 1.391(3) . ?
C1 C2 1.403(2) . ?
C1 N1 1.409(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 Cl2 1.754(2) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.232(2) . ?
C7 N1 1.349(2) . ?
C7 C8 1.506(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 H1N 0.870(16) . ?
Cl1 C13 1.7447(17) . ?
C11 C16 1.392(2) . ?
C11 C12 1.400(2) . ?
C11 N11 1.412(2) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O11 1.236(2) . ?
C17 N11 1.354(2) . ?
C17 C18 1.504(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N11 H11N 0.862(14) . ?
 
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 119.49(18) . . ?
C6 C1 N1 117.75(16) . . ?
C2 C1 N1 122.73(16) . . ?
C3 C2 C1 118.32(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 123.07(19) . . ?
C4 C3 Cl2 119.40(16) . . ?
C2 C3 Cl2 117.51(16) . . ?
C3 C4 C5 117.90(19) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 120.74(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 123.77(16) . . ?
O1 C7 C8 120.82(16) . . ?
N1 C7 C8 115.39(15) . . ?
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 128.06(14) . . ?
C7 N1 H1N 117.7(16) . . ?
C1 N1 H1N 114.1(15) . . ?
C16 C11 C12 120.00(15) . . ?
C16 C11 N11 116.75(14) . . ?
C12 C11 N11 123.23(15) . . ?
C13 C12 C11 117.72(16) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C14 C13 C12 122.95(16) . . ?
C14 C13 Cl1 118.75(14) . . ?
C12 C13 Cl1 118.30(13) . . ?
C13 C14 C15 118.14(16) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 120.63(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.54(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O11 C17 N11 122.38(16) . . ?
O11 C17 C18 121.65(15) . . ?
N11 C17 C18 115.95(15) . . ?
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 127.86(14) . . ?
C17 N11 H11N 116.3(13) . . ?
C11 N11 H11N 115.8(13) . . ?
 
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 O11  0.870(16) 1.960(16) 2.8129(19) 167(2) 3_447
N11 H11N O1  0.862(14) 2.046(15) 2.9008(18) 171.4(18) .
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.216
_refine_diff_density_min   -0.419
_refine_diff_density_rms    0.050
