data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. I. Cunningham
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H21 N O2'
_chemical_formula_sum
 'C21 H21 N O2'
_chemical_formula_weight          319.39
 
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    Pbca
_symmetry_space_group_name_hall   '-P 2ab 2ac'
 
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'
 '-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                    14.0392(3)
_cell_length_b                    13.8109(3)
_cell_length_c                    16.9908(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3294.41(13)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4148
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Slab
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1360
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9789
_exptl_absorpt_correction_T_max   0.9959
_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             28019
_diffrn_reflns_av_R_equivalents   0.0921
_diffrn_reflns_av_sigmaI/netI     0.0541
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.46
_reflns_number_total              3754
_reflns_number_gt                 2874
_reflns_threshold_expression      >2sigma(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 > 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)+(0.0353P)²+1.5271P] 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        0.0079(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3754
_refine_ls_number_parameters      219
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0700
_refine_ls_R_factor_gt            0.0471
_refine_ls_wR_factor_ref          0.1136
_refine_ls_wR_factor_gt           0.1025
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_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 -0.09198(11) 0.18185(12) 0.01587(10) 0.0280(4) Uani 1 1 d . . .
H1A H -0.0721 0.1163 0.0123 0.034 Uiso 1 1 calc R . .
H1B H -0.1424 0.2048 -0.0165 0.034 Uiso 1 1 calc R . .
C2 C -0.04942(11) 0.24144(11) 0.06594(9) 0.0219(3) Uani 1 1 d . . .
C3 C -0.08260(12) 0.34245(12) 0.08313(11) 0.0312(4) Uani 1 1 d . . .
H3A H -0.0413 0.3889 0.0559 0.047 Uiso 1 1 calc R . .
H3B H -0.0799 0.3542 0.1400 0.047 Uiso 1 1 calc R . .
H3C H -0.1483 0.3503 0.0647 0.047 Uiso 1 1 calc R . .
C4 C 0.02960(11) 0.20355(10) 0.11603(9) 0.0212(3) Uani 1 1 d . . .
C5 C 0.12341(11) 0.14272(11) 0.00172(9) 0.0203(3) Uani 1 1 d . . .
C6 C 0.13431(10) 0.24077(11) -0.03425(9) 0.0195(3) Uani 1 1 d . . .
C7 C 0.13445(11) 0.24714(12) -0.11631(9) 0.0242(3) Uani 1 1 d . . .
H7 H 0.1210 0.1914 -0.1471 0.029 Uiso 1 1 calc R . .
C8 C 0.15416(12) 0.33431(12) -0.15282(10) 0.0282(4) Uani 1 1 d . . .
H8 H 0.1527 0.3386 -0.2086 0.034 Uiso 1 1 calc R . .
C9 C 0.17607(12) 0.41554(12) -0.10848(10) 0.0281(4) Uani 1 1 d . . .
H9 H 0.1910 0.4750 -0.1338 0.034 Uiso 1 1 calc R . .
C10 C 0.17616(11) 0.40980(12) -0.02691(10) 0.0256(4) Uani 1 1 d . . .
H10 H 0.1910 0.4654 0.0036 0.031 Uiso 1 1 calc R . .
C11 C 0.15466(11) 0.32304(11) 0.01013(9) 0.0220(3) Uani 1 1 d . . .
H11 H 0.1538 0.3197 0.0660 0.026 Uiso 1 1 calc R . .
C12 C 0.12635(11) 0.05563(10) 0.12712(9) 0.0201(3) Uani 1 1 d . . .
C13 C 0.06306(11) -0.01755(11) 0.14517(9) 0.0230(3) Uani 1 1 d . . .
H13 H -0.0012 -0.0141 0.1280 0.028 Uiso 1 1 calc R . .
C14 C 0.09467(12) -0.09649(12) 0.18887(10) 0.0259(4) Uani 1 1 d . . .
H14 H 0.0518 -0.1469 0.2027 0.031 Uiso 1 1 calc R . .
C15 C 0.18906(12) -0.10100(11) 0.21200(9) 0.0242(3) Uani 1 1 d . . .
H15 H 0.2107 -0.1557 0.2409 0.029 Uiso 1 1 calc R . .
C16 C 0.25341(11) -0.02698(11) 0.19387(9) 0.0215(3) Uani 1 1 d . . .
C17 C 0.22137(11) 0.05395(11) 0.15149(9) 0.0202(3) Uani 1 1 d . . .
C18 C 0.28691(11) 0.13740(11) 0.13198(10) 0.0244(4) Uani 1 1 d . . .
H18A H 0.2534 0.1989 0.1432 0.029 Uiso 1 1 calc R . .
H18B H 0.3014 0.1359 0.0750 0.029 Uiso 1 1 calc R . .
C19 C 0.38037(12) 0.13580(12) 0.17784(11) 0.0316(4) Uani 1 1 d . . .
H19A H 0.4262 0.1813 0.1534 0.038 Uiso 1 1 calc R . .
H19B H 0.3689 0.1572 0.2326 0.038 Uiso 1 1 calc R . .
C20 C 0.42215(12) 0.03447(13) 0.17816(11) 0.0315(4) Uani 1 1 d . . .
H20A H 0.4852 0.0353 0.2043 0.038 Uiso 1 1 calc R . .
H20B H 0.4311 0.0119 0.1234 0.038 Uiso 1 1 calc R . .
C21 C 0.35594(11) -0.03444(12) 0.22150(10) 0.0274(4) Uani 1 1 d . . .
H21A H 0.3785 -0.1017 0.2137 0.033 Uiso 1 1 calc R . .
H21B H 0.3587 -0.0202 0.2786 0.033 Uiso 1 1 calc R . .
N1 N 0.09269(9) 0.13690(9) 0.08052(7) 0.0196(3) Uani 1 1 d . . .
O1 O 0.03656(8) 0.22280(8) 0.18563(6) 0.0282(3) Uani 1 1 d . . .
O2 O 0.14829(8) 0.06981(8) -0.03289(6) 0.0262(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 C2 1.326(2) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C4 1.493(2) . ?
C2 C3 1.499(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.2160(19) . ?
C4 N1 1.4127(19) . ?
C5 O2 1.2172(18) . ?
C5 N1 1.4090(19) . ?
C5 C6 1.493(2) . ?
C6 C11 1.393(2) . ?
C6 C7 1.397(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 C17 1.397(2) . ?
C12 N1 1.4525(19) . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.404(2) . ?
C16 C21 1.518(2) . ?
C17 C18 1.512(2) . ?
C18 C19 1.526(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.521(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
 
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
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C4 118.88(14) . . ?
C1 C2 C3 124.22(15) . . ?
C4 C2 C3 116.48(14) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 120.49(14) . . ?
O1 C4 C2 122.51(14) . . ?
N1 C4 C2 116.80(13) . . ?
O2 C5 N1 119.98(14) . . ?
O2 C5 C6 121.53(14) . . ?
N1 C5 C6 118.16(13) . . ?
C11 C6 C7 119.24(14) . . ?
C11 C6 C5 122.61(14) . . ?
C7 C6 C5 117.76(14) . . ?
C8 C7 C6 120.21(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.36(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.78(15) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.16(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.24(15) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 122.45(14) . . ?
C13 C12 N1 118.53(13) . . ?
C17 C12 N1 119.02(13) . . ?
C12 C13 C14 119.14(15) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.49(15) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.54(15) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 119.21(14) . . ?
C15 C16 C21 119.66(14) . . ?
C17 C16 C21 121.12(14) . . ?
C12 C17 C16 118.13(14) . . ?
C12 C17 C18 120.23(13) . . ?
C16 C17 C18 121.64(13) . . ?
C17 C18 C19 113.60(13) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 110.34(14) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 C21 110.05(14) . . ?
C19 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C20 112.80(13) . . ?
C16 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C16 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C5 N1 C4 124.09(12) . . ?
C5 N1 C12 117.55(12) . . ?
C4 N1 C12 118.34(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.267
_refine_diff_density_min   -0.231
_refine_diff_density_rms    0.053
