 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H21 N O3'
_chemical_formula_weight          335.39
 
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   0.0000
 '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    Cc
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    25.850(3)
_cell_length_b                    4.6425(7)
_cell_length_c                    16.978(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  123.95(3)
_cell_angle_gamma                 90.00
_cell_volume                      1690.2(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8920
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       26.02

_exptl_crystal_description        platelet
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.318
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9816
_exptl_absorpt_correction_T_max   0.9913
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, G.M., 2003)' 

 
_exptl_special_details
;
 ?
;
 
_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    'graphite'
_diffrn_measurement_device_type  
'Bruker-Nonius 95mm CCD camera on κ-goniostat' 
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3938
_diffrn_reflns_av_R_equivalents   0.0703
_diffrn_reflns_av_sigmaI/netI     0.1172
_diffrn_reflns_limit_h_min        -31
_diffrn_reflns_limit_h_max        29
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.80
_diffrn_reflns_theta_max          25.99
_reflns_number_total              1597
_reflns_number_gt                 978
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 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, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ?
_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)+(0.0439P)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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1597
_refine_ls_number_parameters      228
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.1127
_refine_ls_R_factor_gt            0.0532
_refine_ls_wR_factor_ref          0.1122
_refine_ls_wR_factor_gt           0.0955
_refine_ls_goodness_of_fit_ref    0.981
_refine_ls_restrained_S_all       0.980
_refine_ls_shift/su_max           0.002
_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
O1 O 0.19032(15) 0.6307(7) 0.0801(2) 0.0400(9) Uani 1 1 d . . .
O2 O -0.06669(14) 0.6335(6) 0.0439(2) 0.0319(9) Uani 1 1 d . . .
O3 O -0.08760(16) 0.7444(7) -0.1062(2) 0.0372(9) Uani 1 1 d . . .
N1 N 0.12261(17) 0.2853(8) -0.0178(3) 0.0270(10) Uani 1 1 d . . .
C1 C 0.1676(2) 0.4922(10) 0.0052(4) 0.0321(12) Uani 1 1 d . . .
C2 C 0.1858(2) 0.5292(10) -0.0612(3) 0.0266(11) Uani 1 1 d . . .
C3 C 0.1584(2) 0.3723(10) -0.1457(3) 0.0266(12) Uani 1 1 d . . .
C4 C 0.1079(2) 0.1735(9) -0.1690(3) 0.0254(12) Uani 1 1 d . . .
C5 C 0.0900(2) 0.1366(10) -0.1059(3) 0.0265(12) Uani 1 1 d . . .
C6 C 0.2337(2) 0.7312(11) -0.0369(4) 0.0349(13) Uani 1 1 d . . .
H6 H 0.2522 0.8389 0.0203 0.042 Uiso 1 1 calc R . .
C7 C 0.2531(2) 0.7696(11) -0.0963(4) 0.0376(14) Uani 1 1 d . . .
H7 H 0.2849 0.9062 -0.0804 0.045 Uiso 1 1 calc R . .
C8 C 0.2272(3) 0.6131(11) -0.1791(4) 0.0380(13) Uani 1 1 d . . .
H8 H 0.2419 0.6386 -0.2190 0.046 Uiso 1 1 calc R . .
C9 C 0.1798(2) 0.4190(11) -0.2041(3) 0.0332(13) Uani 1 1 d . . .
H9 H 0.1615 0.3154 -0.2620 0.040 Uiso 1 1 calc R . .
C10 C 0.0410(2) -0.0447(10) -0.1286(4) 0.0312(13) Uani 1 1 d . . .
H10 H 0.0281 -0.0621 -0.0863 0.037 Uiso 1 1 calc R . .
C11 C 0.0107(2) -0.1999(10) -0.2118(4) 0.0319(13) Uani 1 1 d . . .
H11 H -0.0226 -0.3251 -0.2263 0.038 Uiso 1 1 calc R . .
C12 C 0.0289(2) -0.1734(10) -0.2742(4) 0.0307(13) Uani 1 1 d . . .
H12 H 0.0087 -0.2838 -0.3310 0.037 Uiso 1 1 calc R . .
C13 C 0.0764(2) 0.0146(9) -0.2536(3) 0.0311(13) Uani 1 1 d . . .
H13 H 0.0880 0.0362 -0.2975 0.037 Uiso 1 1 calc R . .
C14 C 0.1083(2) 0.2291(10) 0.0529(3) 0.0274(12) Uani 1 1 d . . .
H14A H 0.1450 0.2799 0.1167 0.033 Uiso 1 1 calc R . .
H14B H 0.0999 0.0210 0.0529 0.033 Uiso 1 1 calc R . .
C15 C 0.0541(2) 0.3949(10) 0.0336(3) 0.0289(12) Uani 1 1 d . . .
C16 C 0.0102(2) 0.5343(10) 0.0162(3) 0.0293(11) Uani 1 1 d . . .
C17 C -0.0426(2) 0.7261(10) -0.0079(4) 0.0317(12) Uani 1 1 d . . .
H17 H -0.0252 0.9238 0.0149 0.038 Uiso 1 1 calc R . .
C18 C -0.1112(2) 0.8328(10) 0.0382(3) 0.0332(13) Uani 1 1 d . . .
H18A H -0.1501 0.8294 -0.0263 0.040 Uiso 1 1 calc R . .
H18B H -0.0941 1.0309 0.0516 0.040 Uiso 1 1 calc R . .
C19 C -0.1245(3) 0.7430(11) 0.1106(4) 0.0421(15) Uani 1 1 d . . .
H19A H -0.1585 0.8603 0.1029 0.063 Uiso 1 1 calc R . .
H19B H -0.0870 0.7709 0.1746 0.063 Uiso 1 1 calc R . .
H19C H -0.1365 0.5394 0.1014 0.063 Uiso 1 1 calc R . .
C20 C -0.1152(3) 0.4731(11) -0.1516(4) 0.0386(13) Uani 1 1 d . . .
H20A H -0.1246 0.3577 -0.1120 0.046 Uiso 1 1 calc R . .
H20B H -0.0862 0.3622 -0.1606 0.046 Uiso 1 1 calc R . .
C21 C -0.1743(3) 0.5381(12) -0.2461(4) 0.0478(15) Uani 1 1 d . . .
H21A H -0.1935 0.3575 -0.2800 0.072 Uiso 1 1 calc R . .
H21B H -0.1647 0.6582 -0.2838 0.072 Uiso 1 1 calc R . .
H21C H -0.2033 0.6411 -0.2362 0.072 Uiso 1 1 calc R . .
 
 
_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
O1 C1 1.240(6) . ?
O2 C17 1.401(5) . ?
O2 C18 1.437(5) . ?
O3 C17 1.406(6) . ?
O3 C20 1.441(6) . ?
N1 C1 1.385(6) . ?
N1 C5 1.419(6) . ?
N1 C14 1.464(6) . ?
C1 C2 1.457(7) . ?
C2 C3 1.398(6) . ?
C2 C6 1.418(7) . ?
C3 C9 1.395(6) . ?
C3 C4 1.462(6) . ?
C4 C5 1.394(6) . ?
C4 C13 1.402(6) . ?
C5 C10 1.385(6) . ?
C6 C7 1.366(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.375(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.467(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.192(6) . ?
C16 C17 1.481(7) . ?
C17 H17 1.0000 . ?
C18 C19 1.508(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.504(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C17 O2 C18 112.4(3) . . ?
C17 O3 C20 114.6(4) . . ?
C1 N1 C5 123.1(4) . . ?
C1 N1 C14 116.6(4) . . ?
C5 N1 C14 120.3(4) . . ?
O1 C1 N1 119.5(4) . . ?
O1 C1 C2 124.0(4) . . ?
N1 C1 C2 116.6(4) . . ?
C3 C2 C6 120.2(4) . . ?
C3 C2 C1 122.4(4) . . ?
C6 C2 C1 117.4(4) . . ?
C9 C3 C2 118.2(4) . . ?
C9 C3 C4 123.8(4) . . ?
C2 C3 C4 118.0(4) . . ?
C5 C4 C13 118.2(4) . . ?
C5 C4 C3 120.0(4) . . ?
C13 C4 C3 121.8(4) . . ?
C10 C5 C4 120.3(4) . . ?
C10 C5 N1 120.1(4) . . ?
C4 C5 N1 119.6(4) . . ?
C7 C6 C2 119.5(5) . . ?
C7 C6 H6 120.3 . . ?
C2 C6 H6 120.3 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C3 121.2(5) . . ?
C8 C9 H9 119.4 . . ?
C3 C9 H9 119.4 . . ?
C11 C10 C5 120.8(5) . . ?
C11 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C10 C11 C12 119.9(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C4 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C4 C13 H13 119.5 . . ?
N1 C14 C15 111.7(4) . . ?
N1 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 178.2(5) . . ?
C15 C16 C17 175.4(5) . . ?
O2 C17 O3 113.5(4) . . ?
O2 C17 C16 107.8(4) . . ?
O3 C17 C16 112.9(4) . . ?
O2 C17 H17 107.4 . . ?
O3 C17 H17 107.4 . . ?
C16 C17 H17 107.4 . . ?
O2 C18 C19 107.7(4) . . ?
O2 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O2 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 107.5(4) . . ?
O3 C20 H20A 110.2 . . ?
C21 C20 H20A 110.2 . . ?
O3 C20 H20B 110.2 . . ?
C21 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.961
_diffrn_reflns_theta_full              25.99
_diffrn_measured_fraction_theta_full   0.961
_refine_diff_density_max    0.223
_refine_diff_density_min   -0.252
_refine_diff_density_rms    0.051
