data_2009src0949

#Dr. P. Holliman 

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H19 N O3'
_chemical_formula_weight          297.34
 
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                    7.2314(2)
_cell_length_b                    9.4760(3)
_cell_length_c                    11.6165(4)
_cell_angle_alpha                 82.094(2)
_cell_angle_beta                  82.082(2)
_cell_angle_gamma                 78.631(2)
_cell_volume                      767.95(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3455
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Slab
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.11
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.286
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              316
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9861
_exptl_absorpt_correction_T_max   0.9956
_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 12199 reflections reduced R(int) from 0.0715 to 0.0437
Ratio of minimum to maximum apparent transmission: 0.929910
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             13277
_diffrn_reflns_av_R_equivalents   0.0435
_diffrn_reflns_av_sigmaI/netI     0.0423
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3509
_reflns_number_gt                 2951
_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)+(0.0258P)²+0.6463P] 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          3509
_refine_ls_number_parameters      203
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0673
_refine_ls_R_factor_gt            0.0541
_refine_ls_wR_factor_ref          0.1189
_refine_ls_wR_factor_gt           0.1107
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_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 0.2375(2) 0.88754(18) 1.03677(15) 0.0227(4) Uani 1 1 d . . .
C2 C 0.2230(2) 0.96197(18) 0.91173(15) 0.0233(4) Uani 1 1 d . . .
C3 C 0.2115(2) 0.81938(17) 0.88168(14) 0.0197(3) Uani 1 1 d . . .
C4 C 0.2325(2) 0.74691(17) 0.99355(14) 0.0192(3) Uani 1 1 d . . .
C5 C 0.2473(2) 0.59631(17) 1.02666(14) 0.0193(3) Uani 1 1 d . . .
H5 H 0.2412 0.5426 0.9644 0.023 Uiso 1 1 calc R . .
C6 C 0.2689(2) 0.51311(17) 1.13228(14) 0.0178(3) Uani 1 1 d . . .
C7 C 0.2697(2) 0.55742(17) 1.25430(13) 0.0185(3) Uani 1 1 d . . .
C8 C 0.2888(2) 0.41135(17) 1.32834(14) 0.0186(3) Uani 1 1 d . . .
C9 C 0.3019(2) 0.30222(17) 1.25717(14) 0.0182(3) Uani 1 1 d . . .
C10 C 0.3270(2) 0.15692(18) 1.30037(14) 0.0203(3) Uani 1 1 d . . .
H10 H 0.3391 0.0833 1.2505 0.024 Uiso 1 1 calc R . .
C11 C 0.3336(2) 0.12387(19) 1.42044(15) 0.0229(4) Uani 1 1 d . . .
H11 H 0.3498 0.0253 1.4531 0.027 Uiso 1 1 calc R . .
C12 C 0.3172(2) 0.23061(19) 1.49385(15) 0.0233(4) Uani 1 1 d . . .
H12 H 0.3214 0.2047 1.5755 0.028 Uiso 1 1 calc R . .
C13 C 0.2945(2) 0.37680(19) 1.44728(14) 0.0221(3) Uani 1 1 d . . .
H13 H 0.2833 0.4507 1.4967 0.026 Uiso 1 1 calc R . .
C14 C 0.1582(3) 0.86782(19) 0.68328(14) 0.0236(4) Uani 1 1 d . . .
H14A H 0.2585 0.9278 0.6664 0.028 Uiso 1 1 calc R . .
H14B H 0.0335 0.9326 0.6954 0.028 Uiso 1 1 calc R . .
C15 C 0.1630(3) 0.7798(2) 0.58424(15) 0.0271(4) Uani 1 1 d . . .
H15A H 0.2893 0.7200 0.5709 0.041 Uiso 1 1 calc R . .
H15B H 0.1352 0.8449 0.5131 0.041 Uiso 1 1 calc R . .
H15C H 0.0677 0.7172 0.6042 0.041 Uiso 1 1 calc R . .
C16 C 0.0801(2) 0.65540(19) 1.29103(15) 0.0243(4) Uani 1 1 d . . .
H16A H -0.0254 0.6093 1.2804 0.036 Uiso 1 1 calc R . .
H16B H 0.0714 0.7492 1.2427 0.036 Uiso 1 1 calc R . .
H16C H 0.0736 0.6701 1.3735 0.036 Uiso 1 1 calc R . .
C17 C 0.4413(2) 0.62758(19) 1.26267(15) 0.0234(4) Uani 1 1 d . . .
H17A H 0.4422 0.6453 1.3437 0.035 Uiso 1 1 calc R . .
H17B H 0.4323 0.7197 1.2119 0.035 Uiso 1 1 calc R . .
H17C H 0.5587 0.5624 1.2378 0.035 Uiso 1 1 calc R . .
C18 C 0.2739(2) 0.28545(18) 1.04519(14) 0.0214(3) Uani 1 1 d . . .
H18A H 0.1516 0.3211 1.0144 0.032 Uiso 1 1 calc R . .
H18B H 0.2840 0.1823 1.0738 0.032 Uiso 1 1 calc R . .
H18C H 0.3772 0.2986 0.9829 0.032 Uiso 1 1 calc R . .
N1 N 0.28687(19) 0.36639(14) 1.14131(11) 0.0186(3) Uani 1 1 d . . .
O1 O 0.2463(2) 0.92997(13) 1.12949(11) 0.0316(3) Uani 1 1 d . . .
O2 O 0.2258(2) 1.08359(13) 0.86227(11) 0.0311(3) Uani 1 1 d . . .
O3 O 0.19075(18) 0.76366(13) 0.78706(10) 0.0241(3) 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 O1 1.214(2) . ?
C1 C4 1.496(2) . ?
C1 C2 1.533(2) . ?
C2 O2 1.218(2) . ?
C2 C3 1.462(2) . ?
C3 O3 1.3212(19) . ?
C3 C4 1.397(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.375(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.361(2) . ?
C6 C7 1.534(2) . ?
C7 C8 1.518(2) . ?
C7 C16 1.539(2) . ?
C7 C17 1.539(2) . ?
C8 C13 1.380(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.385(2) . ?
C9 N1 1.408(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.4636(19) . ?
C14 C15 1.504(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.462(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
 
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
O1 C1 C4 137.25(16) . . ?
O1 C1 C2 133.93(16) . . ?
C4 C1 C2 88.82(12) . . ?
O2 C2 C3 138.13(17) . . ?
O2 C2 C1 136.02(16) . . ?
C3 C2 C1 85.82(12) . . ?
O3 C3 C4 127.53(15) . . ?
O3 C3 C2 136.80(15) . . ?
C4 C3 C2 95.66(13) . . ?
C3 C4 C5 126.53(15) . . ?
C3 C4 C1 89.60(13) . . ?
C5 C4 C1 143.82(15) . . ?
C6 C5 C4 131.90(15) . . ?
C6 C5 H5 114.1 . . ?
C4 C5 H5 114.1 . . ?
N1 C6 C5 120.88(14) . . ?
N1 C6 C7 108.56(13) . . ?
C5 C6 C7 130.52(14) . . ?
C8 C7 C6 101.30(12) . . ?
C8 C7 C16 110.91(13) . . ?
C6 C7 C16 110.16(13) . . ?
C8 C7 C17 109.41(13) . . ?
C6 C7 C17 112.53(13) . . ?
C16 C7 C17 112.04(14) . . ?
C13 C8 C9 120.01(15) . . ?
C13 C8 C7 130.36(15) . . ?
C9 C8 C7 109.63(13) . . ?
C10 C9 C8 122.47(15) . . ?
C10 C9 N1 128.95(15) . . ?
C8 C9 N1 108.57(14) . . ?
C9 C10 C11 116.76(15) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 122.00(15) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.92(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 118.81(16) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O3 C14 C15 106.22(14) . . ?
O3 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
O3 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 N1 C9 111.90(13) . . ?
C6 N1 C18 124.40(13) . . ?
C9 N1 C18 123.45(13) . . ?
C3 O3 C14 115.52(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.260
_refine_diff_density_min   -0.212
_refine_diff_density_rms    0.050
