 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H21 N O3'
_chemical_formula_sum
 'C17 H21 N O3'
_chemical_formula_weight          287.35
_chemical_absolute_configuration   unk

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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)
_symmetry_space_group_name_hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.9385(8)
_cell_length_b                    13.0338(19)
_cell_length_c                    10.4518(16)
_cell_angle_alpha                 90.00
_cell_angle_beta                  104.583(6)
_cell_angle_gamma                 90.00
_cell_volume                      782.9(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     552
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.219
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              308
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9901
_exptl_absorpt_correction_T_max   0.9992
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2820
_diffrn_reflns_av_R_equivalents   0.1154
_diffrn_reflns_av_sigmaI/netI     0.1169
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.13
_diffrn_reflns_theta_max          27.30
_reflns_number_total              1489
_reflns_number_gt                 1232
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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 > 2σ(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)+(0.0903P)²+0.1655P] 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        0.18(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1489
_refine_ls_number_parameters      194
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0907
_refine_ls_R_factor_gt            0.0735
_refine_ls_wR_factor_ref          0.1968
_refine_ls_wR_factor_gt           0.1785
_refine_ls_goodness_of_fit_ref    1.131
_refine_ls_restrained_S_all       1.131
_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
C2 C 0.3565(9) 0.6722(5) 0.3206(5) 0.0225(11) Uani 1 1 d . . .
H2 H 0.5291 0.6686 0.3342 0.027 Uiso 1 1 calc R . .
C4 C 0.0591(9) 0.5578(4) 0.1904(5) 0.0233(12) Uani 1 1 d . . .
H4 H -0.1000 0.5865 0.1529 0.028 Uiso 1 1 calc R . .
C5 C 0.1023(9) 0.5411(5) 0.3406(5) 0.0275(12) Uani 1 1 d . . .
C6 C 0.2846(8) 0.7826(4) 0.3496(5) 0.0223(11) Uani 1 1 d . . .
C7 C 0.3509(10) 0.8588(5) 0.2526(5) 0.0276(12) Uani 1 1 d . . .
H7A H 0.3231 0.9291 0.2783 0.041 Uiso 1 1 calc R . .
H7B H 0.2559 0.8454 0.1630 0.041 Uiso 1 1 calc R . .
H7C H 0.5158 0.8505 0.2547 0.041 Uiso 1 1 calc R . .
C8 C 0.4199(10) 0.8113(5) 0.4919(5) 0.0320(14) Uani 1 1 d . . .
H8A H 0.3763 0.7644 0.5549 0.048 Uiso 1 1 calc R . .
H8B H 0.3816 0.8819 0.5112 0.048 Uiso 1 1 calc R . .
H8C H 0.5874 0.8059 0.4997 0.048 Uiso 1 1 calc R . .
C9 C 0.0224(9) 0.7898(5) 0.3399(5) 0.0267(13) Uani 1 1 d . . .
H9A H -0.0652 0.7707 0.2505 0.040 Uiso 1 1 calc R . .
H9B H -0.0171 0.8603 0.3587 0.040 Uiso 1 1 calc R . .
H9C H -0.0176 0.7430 0.4042 0.040 Uiso 1 1 calc R . .
C10 C 0.3525(8) 0.6461(4) 0.0876(5) 0.0185(11) Uani 1 1 d . . .
C11 C 0.2148(8) 0.6286(4) -0.0523(5) 0.0197(11) Uani 1 1 d . . .
C12 C 0.3264(9) 0.5861(5) -0.1433(5) 0.0230(11) Uani 1 1 d . . .
H12 H 0.4829 0.5631 -0.1147 0.028 Uiso 1 1 calc R . .
C13 C 0.2065(10) 0.5777(5) -0.2758(5) 0.0269(13) Uani 1 1 d . . .
H13 H 0.2804 0.5481 -0.3378 0.032 Uiso 1 1 calc R . .
C14 C -0.0215(10) 0.6126(5) -0.3172(5) 0.0301(14) Uani 1 1 d . . .
H14 H -0.1031 0.6066 -0.4076 0.036 Uiso 1 1 calc R . .
C15 C -0.1305(9) 0.6559(4) -0.2284(5) 0.0243(12) Uani 1 1 d . . .
H15 H -0.2852 0.6808 -0.2583 0.029 Uiso 1 1 calc R . .
C16 C -0.0146(8) 0.6635(4) -0.0945(5) 0.0213(11) Uani 1 1 d . . .
H16 H -0.0909 0.6919 -0.0330 0.026 Uiso 1 1 calc R . .
C17 C 0.0864(9) 0.4535(4) 0.1262(5) 0.0231(12) Uani 1 1 d . . .
H17A H -0.0204 0.4035 0.1513 0.028 Uiso 1 1 calc R . .
H17B H 0.0383 0.4614 0.0289 0.028 Uiso 1 1 calc R . .
C18 C 0.3265(9) 0.4112(4) 0.1640(6) 0.0275(12) Uani 1 1 d . . .
H18 H 0.4063 0.4135 0.2549 0.033 Uiso 1 1 calc R . .
C19 C 0.4386(11) 0.3705(5) 0.0815(7) 0.0380(16) Uani 1 1 d . . .
H19A H 0.3652 0.3667 -0.0103 0.046 Uiso 1 1 calc R . .
H19B H 0.5924 0.3452 0.1142 0.046 Uiso 1 1 calc R . .
N3 N 0.2398(7) 0.6353(4) 0.1862(4) 0.0200(10) Uani 1 1 d . . .
O1 O 0.2837(7) 0.5992(3) 0.4066(3) 0.0287(10) Uani 1 1 d . . .
O2 O -0.0029(9) 0.4839(4) 0.3947(4) 0.0446(13) Uani 1 1 d . . .
O3 O 0.5561(6) 0.6767(3) 0.1103(3) 0.0234(9) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C2 O1 1.447(7) . ?
C2 N3 1.482(6) . ?
C2 C6 1.553(8) . ?
C2 H2 1.0000 . ?
C4 N3 1.483(7) . ?
C4 C5 1.541(7) . ?
C4 C17 1.542(8) . ?
C4 H4 1.0000 . ?
C5 O2 1.202(7) . ?
C5 O1 1.355(7) . ?
C6 C9 1.537(7) . ?
C6 C7 1.540(8) . ?
C6 C8 1.548(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O3 1.238(6) . ?
C10 N3 1.370(6) . ?
C10 C11 1.502(6) . ?
C11 C16 1.398(7) . ?
C11 C12 1.403(7) . ?
C12 C13 1.393(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.487(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.326(8) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
 
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 C2 N3 103.5(4) . . ?
O1 C2 C6 110.4(4) . . ?
N3 C2 C6 113.5(4) . . ?
O1 C2 H2 109.7 . . ?
N3 C2 H2 109.7 . . ?
C6 C2 H2 109.7 . . ?
N3 C4 C5 101.0(4) . . ?
N3 C4 C17 115.6(4) . . ?
C5 C4 C17 108.1(4) . . ?
N3 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
C17 C4 H4 110.6 . . ?
O2 C5 O1 123.3(5) . . ?
O2 C5 C4 126.4(5) . . ?
O1 C5 C4 110.3(5) . . ?
C9 C6 C7 109.9(4) . . ?
C9 C6 C8 108.7(4) . . ?
C7 C6 C8 108.7(5) . . ?
C9 C6 C2 111.6(4) . . ?
C7 C6 C2 109.9(4) . . ?
C8 C6 C2 108.1(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N3 121.8(4) . . ?
O3 C10 C11 120.1(4) . . ?
N3 C10 C11 117.8(4) . . ?
C16 C11 C12 120.3(4) . . ?
C16 C11 C10 120.4(4) . . ?
C12 C11 C10 119.0(4) . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.2(5) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C4 114.2(4) . . ?
C18 C17 H17A 108.7 . . ?
C4 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C4 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 125.5(5) . . ?
C19 C18 H18 117.2 . . ?
C17 C18 H18 117.2 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C10 N3 C2 118.7(4) . . ?
C10 N3 C4 125.9(4) . . ?
C2 N3 C4 111.2(4) . . ?
C5 O1 C2 112.0(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.807
_diffrn_reflns_theta_full              27.30
_diffrn_measured_fraction_theta_full   0.807
_refine_diff_density_max    0.299
_refine_diff_density_min   -0.323
_refine_diff_density_rms    0.082
