data_2009src0583
 
#Dr. P. Holliman

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H13 N O2'
_chemical_formula_weight          203.23
 
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    Pbcn
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    39.9227(15)
_cell_length_b                    8.3170(3)
_cell_length_c                    12.9213(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      4290.4(3)
_cell_formula_units_Z             16
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4949
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Slab'
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.259
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1728
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9864
_exptl_absorpt_correction_T_max   0.9966
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 19990 reflections reduced R(int) from 0.1897 to 0.0660
Ratio of minimum to maximum apparent transmission: 0.836914
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_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             22351
_diffrn_reflns_av_R_equivalents   0.0637
_diffrn_reflns_av_sigmaI/netI     0.0543
_diffrn_reflns_limit_h_min        -51
_diffrn_reflns_limit_h_max        51
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4862
_reflns_number_gt                 3702
_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, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0078P)²+7.5015P] 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          4862
_refine_ls_number_parameters      279
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1007
_refine_ls_R_factor_gt            0.0711
_refine_ls_wR_factor_ref          0.1450
_refine_ls_wR_factor_gt           0.1292
_refine_ls_goodness_of_fit_ref    1.103
_refine_ls_restrained_S_all       1.103
_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 0.02512(6) 0.0350(3) 0.37621(19) 0.0221(5) Uani 1 1 d . . .
C2 C 0.04347(6) 0.0630(3) 0.27806(18) 0.0210(5) Uani 1 1 d . . .
C3 C 0.04811(6) 0.2217(3) 0.24451(18) 0.0206(5) Uani 1 1 d . . .
H3 H 0.0399 0.3098 0.2839 0.025 Uiso 1 1 calc R . .
C4 C 0.06487(5) 0.2461(3) 0.15272(18) 0.0196(5) Uani 1 1 d . . .
C5 C 0.07691(6) 0.1154(3) 0.09595(18) 0.0208(5) Uani 1 1 d . . .
C6 C 0.07244(6) -0.0416(3) 0.12765(19) 0.0251(5) Uani 1 1 d . . .
H6 H 0.0807 -0.1293 0.0880 0.030 Uiso 1 1 calc R . .
C7 C 0.05536(6) -0.0660(3) 0.2199(2) 0.0262(6) Uani 1 1 d . . .
H7 H 0.0517 -0.1726 0.2438 0.031 Uiso 1 1 calc R . .
C8 C 0.07385(6) 0.3972(3) 0.09385(18) 0.0206(5) Uani 1 1 d . . .
C9 C 0.09311(6) 0.3227(3) 0.00420(19) 0.0229(5) Uani 1 1 d . . .
C10 C 0.11043(7) 0.4200(3) -0.0753(2) 0.0329(6) Uani 1 1 d . . .
H10A H 0.1298 0.4740 -0.0441 0.049 Uiso 1 1 calc R . .
H10B H 0.0949 0.5007 -0.1030 0.049 Uiso 1 1 calc R . .
H10C H 0.1181 0.3498 -0.1315 0.049 Uiso 1 1 calc R . .
C11 C 0.09642(6) 0.5113(3) 0.15534(19) 0.0252(5) Uani 1 1 d . . .
H11A H 0.0836 0.5595 0.2120 0.038 Uiso 1 1 calc R . .
H11B H 0.1047 0.5963 0.1095 0.038 Uiso 1 1 calc R . .
H11C H 0.1154 0.4510 0.1838 0.038 Uiso 1 1 calc R . .
C12 C 0.04269(6) 0.4862(3) 0.0543(2) 0.0291(6) Uani 1 1 d . . .
H12A H 0.0291 0.4130 0.0121 0.044 Uiso 1 1 calc R . .
H12B H 0.0496 0.5783 0.0122 0.044 Uiso 1 1 calc R . .
H12C H 0.0294 0.5240 0.1133 0.044 Uiso 1 1 calc R . .
N1 N 0.09402(5) 0.1670(3) 0.00510(15) 0.0231(4) Uani 1 1 d . . .
O1 O 0.01899(4) -0.1149(2) 0.39968(14) 0.0294(4) Uani 1 1 d . . .
H1 H 0.0071 -0.1187 0.4533 0.044 Uiso 1 1 calc R . .
O2 O 0.01628(4) 0.1496(2) 0.43165(13) 0.0282(4) Uani 1 1 d . . .
C21 C 0.14230(6) 0.1275(3) 0.37911(19) 0.0251(5) Uani 1 1 d . . .
C22 C 0.15877(6) 0.2051(3) 0.28795(18) 0.0208(5) Uani 1 1 d . . .
C23 C 0.17506(6) 0.3528(3) 0.30251(19) 0.0224(5) Uani 1 1 d . . .
H23 H 0.1768 0.3993 0.3695 0.027 Uiso 1 1 calc R . .
C24 C 0.18858(6) 0.4290(3) 0.21727(19) 0.0210(5) Uani 1 1 d . . .
C25 C 0.18627(6) 0.3604(3) 0.11901(18) 0.0209(5) Uani 1 1 d . . .
C26 C 0.17115(6) 0.2122(3) 0.10385(19) 0.0230(5) Uani 1 1 d . . .
H26 H 0.1703 0.1644 0.0371 0.028 Uiso 1 1 calc R . .
C27 C 0.15727(6) 0.1357(3) 0.18971(19) 0.0223(5) Uani 1 1 d . . .
H27 H 0.1466 0.0345 0.1812 0.027 Uiso 1 1 calc R . .
C28 C 0.20627(6) 0.5884(3) 0.2057(2) 0.0240(5) Uani 1 1 d . . .
C29 C 0.21137(6) 0.5881(3) 0.0886(2) 0.0274(6) Uani 1 1 d . . .
C30 C 0.22755(7) 0.7234(4) 0.0325(2) 0.0409(7) Uani 1 1 d . . .
H30A H 0.2305 0.6943 -0.0404 0.061 Uiso 1 1 calc R . .
H30B H 0.2495 0.7458 0.0634 0.061 Uiso 1 1 calc R . .
H30C H 0.2134 0.8193 0.0375 0.061 Uiso 1 1 calc R . .
C31 C 0.24006(6) 0.5920(3) 0.2634(2) 0.0298(6) Uani 1 1 d . . .
H31A H 0.2361 0.5825 0.3380 0.045 Uiso 1 1 calc R . .
H31B H 0.2516 0.6936 0.2488 0.045 Uiso 1 1 calc R . .
H31C H 0.2540 0.5020 0.2401 0.045 Uiso 1 1 calc R . .
C32 C 0.18431(7) 0.7296(3) 0.2405(3) 0.0374(7) Uani 1 1 d . . .
H32A H 0.1629 0.7265 0.2031 0.056 Uiso 1 1 calc R . .
H32B H 0.1958 0.8310 0.2255 0.056 Uiso 1 1 calc R . .
H32C H 0.1801 0.7214 0.3150 0.056 Uiso 1 1 calc R . .
N21 N 0.20042(5) 0.4610(3) 0.04136(16) 0.0274(5) Uani 1 1 d . . .
O21 O 0.12882(5) -0.0138(2) 0.35676(14) 0.0313(4) Uani 1 1 d . . .
H21 H 0.1187 -0.0493 0.4089 0.047 Uiso 1 1 calc R . .
O22 O 0.14099(5) 0.1888(2) 0.46467(15) 0.0398(5) 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 O2 1.244(3) . ?
C1 O1 1.306(3) . ?
C1 C2 1.483(3) . ?
C2 C7 1.393(3) . ?
C2 C3 1.402(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 C8 1.512(3) . ?
C5 C6 1.380(3) . ?
C5 N1 1.424(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.522(3) . ?
C8 C11 1.531(3) . ?
C8 C12 1.535(3) . ?
C9 N1 1.296(3) . ?
C9 C10 1.480(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 H1 0.8400 . ?
C21 O22 1.219(3) . ?
C21 O21 1.324(3) . ?
C21 C22 1.495(3) . ?
C22 C27 1.395(3) . ?
C22 C23 1.403(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.395(3) . ?
C24 C28 1.510(3) . ?
C25 C26 1.386(3) . ?
C25 N21 1.424(3) . ?
C26 C27 1.394(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.526(4) . ?
C28 C32 1.532(4) . ?
C28 C31 1.542(3) . ?
C29 N21 1.296(3) . ?
C29 C30 1.487(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O21 H21 0.8400 . ?
 
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
O2 C1 O1 123.0(2) . . ?
O2 C1 C2 120.8(2) . . ?
O1 C1 C2 116.2(2) . . ?
C7 C2 C3 120.9(2) . . ?
C7 C2 C1 120.6(2) . . ?
C3 C2 C1 118.5(2) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 C8 132.2(2) . . ?
C5 C4 C8 107.51(19) . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 N1 126.3(2) . . ?
C4 C5 N1 111.3(2) . . ?
C5 C6 C7 117.2(2) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C2 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C4 C8 C9 99.47(18) . . ?
C4 C8 C11 113.2(2) . . ?
C9 C8 C11 110.48(19) . . ?
C4 C8 C12 112.09(19) . . ?
C9 C8 C12 110.6(2) . . ?
C11 C8 C12 110.5(2) . . ?
N1 C9 C10 122.7(2) . . ?
N1 C9 C8 114.5(2) . . ?
C10 C9 C8 122.8(2) . . ?
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 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 N1 C5 107.2(2) . . ?
C1 O1 H1 109.5 . . ?
O22 C21 O21 123.5(2) . . ?
O22 C21 C22 123.5(2) . . ?
O21 C21 C22 112.9(2) . . ?
C27 C22 C23 120.2(2) . . ?
C27 C22 C21 121.3(2) . . ?
C23 C22 C21 118.4(2) . . ?
C24 C23 C22 118.4(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 120.8(2) . . ?
C23 C24 C28 131.7(2) . . ?
C25 C24 C28 107.5(2) . . ?
C26 C25 C24 121.4(2) . . ?
C26 C25 N21 126.6(2) . . ?
C24 C25 N21 112.0(2) . . ?
C25 C26 C27 117.8(2) . . ?
C25 C26 H26 121.1 . . ?
C27 C26 H26 121.1 . . ?
C26 C27 C22 121.2(2) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C24 C28 C29 99.1(2) . . ?
C24 C28 C32 112.1(2) . . ?
C29 C28 C32 111.6(2) . . ?
C24 C28 C31 112.2(2) . . ?
C29 C28 C31 111.3(2) . . ?
C32 C28 C31 110.1(2) . . ?
N21 C29 C30 122.3(2) . . ?
N21 C29 C28 115.1(2) . . ?
C30 C29 C28 122.7(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 N21 C25 106.3(2) . . ?
C21 O21 H21 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
O1 H1 O2  0.84 1.77 2.611(2) 173.4 5_556
O21 H21 N1  0.84 1.86 2.688(3) 167.1 7_556
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.288
_refine_diff_density_min   -0.319
_refine_diff_density_rms    0.063
