 
data_2009lsh001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
N-butyryl-N-(2-cyanophenyl)butanamide 
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H18 N2 O2'
_chemical_formula_weight          258.31
 
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    P21/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    8.0497(2)
_cell_length_b                    17.7203(3)
_cell_length_c                    10.1483(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.323(2)
_cell_angle_gamma                 90.00
_cell_volume                      1414.23(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11877
_cell_measurement_theta_min       23.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut block'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.90
_exptl_crystal_size_mid           0.60
_exptl_crystal_size_min           0.60
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.213
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              552
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9303
_exptl_absorpt_correction_T_max   0.9528
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
The Tmin and Tmax values above were generated with the
SIZE command in SHELXL and rely entirely on the crystal 
dimensions given. 
SADABS estimates the minimum and maximum transmission
as 0.6461 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             17900
_diffrn_reflns_av_R_equivalents   0.0359
_diffrn_reflns_av_sigmaI/netI     0.0261
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_k_max        23
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3234
_reflns_number_gt                 2797
_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.
;
 
_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)+(0.0421P)²+0.5343P] 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_number_reflns          3234
_refine_ls_number_parameters      174
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0479
_refine_ls_R_factor_gt            0.0401
_refine_ls_wR_factor_ref          0.0986
_refine_ls_wR_factor_gt           0.0943
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.033
_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 0.68858(13) 0.14013(6) 0.69714(10) 0.0138(2) Uani 1 1 d . . .
C2 C 0.83393(13) 0.17611(6) 0.77061(10) 0.0146(2) Uani 1 1 d . . .
C3 C 0.82140(15) 0.22586(6) 0.87481(11) 0.0182(2) Uani 1 1 d . . .
H3 H 0.9201 0.2499 0.9253 0.022 Uiso 1 1 calc R . .
C4 C 0.66354(15) 0.23981(6) 0.90387(11) 0.0204(2) Uani 1 1 d . . .
H4 H 0.6541 0.2735 0.9748 0.025 Uiso 1 1 calc R . .
C5 C 0.51899(15) 0.20470(6) 0.82956(11) 0.0196(2) Uani 1 1 d . . .
H5 H 0.4112 0.2148 0.8497 0.024 Uiso 1 1 calc R . .
C6 C 0.53111(14) 0.15482(6) 0.72561(11) 0.0172(2) Uani 1 1 d . . .
H6 H 0.4320 0.1311 0.6748 0.021 Uiso 1 1 calc R . .
C7 C 0.70779(15) 0.00939(6) 0.61871(11) 0.0190(2) Uani 1 1 d . . .
C8 C 0.72967(15) -0.01269(6) 0.76542(11) 0.0193(2) Uani 1 1 d . . .
H8A H 0.6309 0.0056 0.8000 0.023 Uiso 1 1 calc R . .
H8B H 0.8330 0.0118 0.8186 0.023 Uiso 1 1 calc R . .
C9 C 0.74503(17) -0.09784(6) 0.78395(12) 0.0233(3) Uani 1 1 d . . .
H9A H 0.8432 -0.1160 0.7484 0.028 Uiso 1 1 calc R . .
H9B H 0.6413 -0.1222 0.7310 0.028 Uiso 1 1 calc R . .
C10 C 0.7684(2) -0.12117(7) 0.93122(14) 0.0352(3) Uani 1 1 d . . .
H10A H 0.8713 -0.0975 0.9840 0.053 Uiso 1 1 calc R . .
H10B H 0.7793 -0.1762 0.9384 0.053 Uiso 1 1 calc R . .
H10C H 0.6695 -0.1049 0.9660 0.053 Uiso 1 1 calc R . .
C11 C 0.71230(13) 0.12088(6) 0.46595(10) 0.0159(2) Uani 1 1 d . . .
C12 C 0.73803(15) 0.07135(6) 0.35130(11) 0.0198(2) Uani 1 1 d . . .
H12A H 0.6430 0.0349 0.3294 0.024 Uiso 1 1 calc R . .
H12B H 0.8446 0.0423 0.3803 0.024 Uiso 1 1 calc R . .
C13 C 0.74726(17) 0.11620(7) 0.22520(12) 0.0248(3) Uani 1 1 d . . .
H13A H 0.8488 0.1492 0.2437 0.030 Uiso 1 1 calc R . .
H13B H 0.6454 0.1487 0.1998 0.030 Uiso 1 1 calc R . .
C14 C 0.7570(2) 0.06292(8) 0.10914(13) 0.0320(3) Uani 1 1 d . . .
H14A H 0.6544 0.0315 0.0889 0.048 Uiso 1 1 calc R . .
H14B H 0.8574 0.0305 0.1347 0.048 Uiso 1 1 calc R . .
H14C H 0.7654 0.0924 0.0292 0.048 Uiso 1 1 calc R . .
C15 C 0.99468(15) 0.16063(6) 0.73586(11) 0.0200(2) Uani 1 1 d . . .
N1 N 0.70447(11) 0.08758(5) 0.59165(9) 0.0146(2) Uani 1 1 d . . .
N2 N 1.12018(14) 0.14676(7) 0.70491(12) 0.0335(3) Uani 1 1 d . . .
O1 O 0.69520(14) -0.03740(5) 0.53028(9) 0.0343(3) Uani 1 1 d . . .
O2 O 0.70128(11) 0.18902(4) 0.45630(8) 0.02221(19) 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 C6 1.3836(15) . ?
C1 C2 1.3996(15) . ?
C1 N1 1.4450(13) . ?
C2 C3 1.3968(15) . ?
C2 C15 1.4383(15) . ?
C3 C4 1.3866(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3911(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3956(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.2100(14) . ?
C7 N1 1.4117(14) . ?
C7 C8 1.5129(15) . ?
C8 C9 1.5224(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5232(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.2132(14) . ?
C11 N1 1.4191(13) . ?
C11 C12 1.5066(14) . ?
C12 C13 1.5216(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5246(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N2 1.1468(16) . ?
 
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 120.13(10) . . ?
C6 C1 N1 120.39(9) . . ?
C2 C1 N1 119.48(9) . . ?
C3 C2 C1 120.24(10) . . ?
C3 C2 C15 121.34(10) . . ?
C1 C2 C15 118.43(9) . . ?
C4 C3 C2 119.41(10) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.23(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.51(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.47(10) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C7 N1 122.22(10) . . ?
O1 C7 C8 121.76(10) . . ?
N1 C7 C8 116.02(9) . . ?
C7 C8 C9 111.55(9) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 112.33(10) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 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 . . ?
O2 C11 N1 118.03(9) . . ?
O2 C11 C12 122.50(10) . . ?
N1 C11 C12 119.46(9) . . ?
C11 C12 C13 112.62(9) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 110.25(10) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C2 177.77(13) . . ?
C7 N1 C11 125.48(9) . . ?
C7 N1 C1 119.30(8) . . ?
C11 N1 C1 115.21(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.277
_refine_diff_density_min   -0.215
_refine_diff_density_rms    0.040
