data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. A. K. Croft
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H22 N2 O2'
_chemical_formula_sum
 'C20 H22 N2 O2'
_chemical_formula_weight          322.40
 
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    P2(1)/c
_symmetry_spacE_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    15.2187(13)
_cell_length_b                    14.3684(10)
_cell_length_c                    7.6880(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  100.254(4)
_cell_angle_gamma                 90.00
_cell_volume                      1654.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3787
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.294
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9768
_exptl_absorpt_correction_T_max   0.9966
_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             19071
_diffrn_reflns_av_R_equivalents   0.0981
_diffrn_reflns_av_sigmaI/netI     0.0936
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.04
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3763
_reflns_number_gt                 2098
_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)+(0.0516P)²+0.0000P] 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        0.028(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3763
_refine_ls_number_parameters      220
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1231
_refine_ls_R_factor_gt            0.0519
_refine_ls_wR_factor_ref          0.1187
_refine_ls_wR_factor_gt           0.0974
_refine_ls_goodness_of_fit_ref    0.991
_refine_ls_restrained_S_all       0.991
_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 0.38374(13) 0.46759(13) 0.1378(2) 0.0281(5) Uani 1 1 d . . .
C2 C 0.42427(13) 0.56338(13) 0.1431(2) 0.0266(5) Uani 1 1 d . . .
H2 H 0.4830 0.5566 0.1031 0.032 Uiso 1 1 calc R . .
C3 C 0.40734(13) 0.57673(13) 0.4563(2) 0.0257(4) Uani 1 1 d . . .
C4 C 0.34643(13) 0.49225(12) 0.4352(2) 0.0251(4) Uani 1 1 d . . .
H4 H 0.3685 0.4505 0.5377 0.030 Uiso 1 1 calc R . .
C5 C 0.30773(15) 0.34574(13) 0.2627(3) 0.0338(5) Uani 1 1 d . . .
H5A H 0.2450 0.3511 0.2056 0.051 Uiso 1 1 calc R . .
H5B H 0.3112 0.3196 0.3814 0.051 Uiso 1 1 calc R . .
H5C H 0.3392 0.3048 0.1924 0.051 Uiso 1 1 calc R . .
C6 C 0.50332(13) 0.68536(13) 0.3368(3) 0.0288(5) Uani 1 1 d . . .
H6A H 0.4706 0.7405 0.2857 0.043 Uiso 1 1 calc R . .
H6B H 0.5530 0.6729 0.2746 0.043 Uiso 1 1 calc R . .
H6C H 0.5267 0.6964 0.4623 0.043 Uiso 1 1 calc R . .
C7 C 0.36585(13) 0.62733(14) 0.0067(2) 0.0316(5) Uani 1 1 d . . .
H7A H 0.3936 0.6898 0.0123 0.038 Uiso 1 1 calc R . .
H7B H 0.3656 0.6022 -0.1132 0.038 Uiso 1 1 calc R . .
C8 C 0.27073(13) 0.63734(13) 0.0339(2) 0.0268(5) Uani 1 1 d . . .
C9 C 0.24481(14) 0.70864(13) 0.1352(2) 0.0309(5) Uani 1 1 d . . .
H9 H 0.2875 0.7535 0.1867 0.037 Uiso 1 1 calc R . .
C10 C 0.15761(15) 0.71549(14) 0.1624(3) 0.0348(5) Uani 1 1 d . . .
H10 H 0.1412 0.7643 0.2335 0.042 Uiso 1 1 calc R . .
C11 C 0.09437(14) 0.65170(14) 0.0866(3) 0.0343(5) Uani 1 1 d . . .
H11 H 0.0343 0.6569 0.1041 0.041 Uiso 1 1 calc R . .
C12 C 0.11911(14) 0.58034(14) -0.0149(3) 0.0333(5) Uani 1 1 d . . .
H12 H 0.0760 0.5360 -0.0669 0.040 Uiso 1 1 calc R . .
C13 C 0.20644(14) 0.57319(13) -0.0412(2) 0.0298(5) Uani 1 1 d . . .
H13 H 0.2228 0.5239 -0.1114 0.036 Uiso 1 1 calc R . .
C14 C 0.25151(13) 0.52274(13) 0.4546(2) 0.0285(5) Uani 1 1 d . . .
H14A H 0.2570 0.5724 0.5452 0.034 Uiso 1 1 calc R . .
H14B H 0.2223 0.5506 0.3411 0.034 Uiso 1 1 calc R . .
C15 C 0.19039(13) 0.44819(12) 0.5045(2) 0.0261(4) Uani 1 1 d . . .
C16 C 0.21552(13) 0.39332(13) 0.6546(2) 0.0277(5) Uani 1 1 d . . .
H16 H 0.2739 0.3993 0.7225 0.033 Uiso 1 1 calc R . .
C17 C 0.15613(14) 0.33011(13) 0.7058(3) 0.0319(5) Uani 1 1 d . . .
H17 H 0.1737 0.2937 0.8093 0.038 Uiso 1 1 calc R . .
C18 C 0.07190(15) 0.31986(14) 0.6076(3) 0.0349(5) Uani 1 1 d . . .
H18 H 0.0316 0.2760 0.6422 0.042 Uiso 1 1 calc R . .
C19 C 0.04631(15) 0.37365(15) 0.4586(3) 0.0396(5) Uani 1 1 d . . .
H19 H -0.0118 0.3669 0.3902 0.048 Uiso 1 1 calc R . .
C20 C 0.10520(14) 0.43748(14) 0.4086(3) 0.0337(5) Uani 1 1 d . . .
H20 H 0.0867 0.4746 0.3064 0.040 Uiso 1 1 calc R . .
N1 N 0.34905(11) 0.43747(10) 0.2756(2) 0.0268(4) Uani 1 1 d . . .
N2 N 0.44309(10) 0.60512(10) 0.31865(19) 0.0241(4) Uani 1 1 d . . .
O1 O 0.38236(9) 0.41989(9) 0.00332(17) 0.0343(4) Uani 1 1 d . . .
O2 O 0.42191(9) 0.61583(9) 0.60116(17) 0.0353(4) 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 1.237(2) . ?
C1 N1 1.337(3) . ?
C1 C2 1.506(3) . ?
C2 N2 1.458(2) . ?
C2 C7 1.550(3) . ?
C2 H2 1.0000 . ?
C3 O2 1.232(2) . ?
C3 N2 1.337(2) . ?
C3 C4 1.518(3) . ?
C4 N1 1.464(2) . ?
C4 C14 1.542(3) . ?
C4 H4 1.0000 . ?
C5 N1 1.456(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.464(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.386(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.381(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 H20 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 C1 N1 122.16(18) . . ?
O1 C1 C2 118.35(17) . . ?
N1 C1 C2 119.47(16) . . ?
N2 C2 C1 114.41(15) . . ?
N2 C2 C7 112.14(15) . . ?
C1 C2 C7 109.91(15) . . ?
N2 C2 H2 106.6 . . ?
C1 C2 H2 106.6 . . ?
C7 C2 H2 106.6 . . ?
O2 C3 N2 122.91(18) . . ?
O2 C3 C4 117.99(17) . . ?
N2 C3 C4 119.09(16) . . ?
N1 C4 C3 114.33(16) . . ?
N1 C4 C14 113.55(15) . . ?
C3 C4 C14 109.10(15) . . ?
N1 C4 H4 106.4 . . ?
C3 C4 H4 106.4 . . ?
C14 C4 H4 106.4 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 114.37(16) . . ?
C8 C7 H7A 108.7 . . ?
C2 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C2 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 118.23(18) . . ?
C9 C8 C7 121.70(18) . . ?
C13 C8 C7 120.06(17) . . ?
C10 C9 C8 120.94(19) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.5(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.23(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.84(18) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C15 C14 C4 116.90(15) . . ?
C15 C14 H14A 108.1 . . ?
C4 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
C4 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C20 C15 C16 118.19(18) . . ?
C20 C15 C14 120.29(17) . . ?
C16 C15 C14 121.36(18) . . ?
C17 C16 C15 120.58(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.35(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.60(19) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 121.20(19) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C1 N1 C5 117.76(16) . . ?
C1 N1 C4 124.30(16) . . ?
C5 N1 C4 117.88(16) . . ?
C3 N2 C2 124.51(16) . . ?
C3 N2 C6 120.07(15) . . ?
C2 N2 C6 115.39(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.193
_refine_diff_density_min   -0.227
_refine_diff_density_rms    0.051
