data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H25 N O2'
_chemical_formula_weight          323.42
 
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    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                    7.7318(15)
_cell_length_b                    27.917(6)
_cell_length_c                    16.430(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.48(3)
_cell_angle_gamma                 90.00
_cell_volume                      3462.6(12)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10855
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        colourless
_exptl_crystal_colour             needle
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.241
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1392
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9616
_exptl_absorpt_correction_T_max   0.9984
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(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        '\\f and \\w 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             11415
_diffrn_reflns_av_R_equivalents   0.1322
_diffrn_reflns_av_sigmaI/netI     0.1751
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -32
_diffrn_reflns_limit_k_max        34
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          25.99
_reflns_number_total              5912
_reflns_number_gt                 3260
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.1532P)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        0.0115(17)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    9(4)
_refine_ls_number_reflns          5912
_refine_ls_number_parameters      452
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.1774
_refine_ls_R_factor_gt            0.1084
_refine_ls_wR_factor_ref          0.2832
_refine_ls_wR_factor_gt           0.2424
_refine_ls_goodness_of_fit_ref    1.015
_refine_ls_restrained_S_all       1.014
_refine_ls_shift/su_max           0.016
_refine_ls_shift/su_mean          0.001
 
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 1.0586(11) 0.2182(3) 0.2858(5) 0.056(2) Uani 1 1 d . . .
C2 C 1.0495(10) 0.2328(3) 0.2032(5) 0.058(2) Uani 1 1 d . . .
H2 H 1.1264 0.2187 0.1721 0.070 Uiso 1 1 calc R . .
C3 C 0.9290(12) 0.2678(3) 0.1662(6) 0.058(2) Uani 1 1 d . . .
H3 H 0.9327 0.2796 0.1124 0.070 Uiso 1 1 calc R . .
C4 C 0.8054(12) 0.2851(3) 0.2070(6) 0.057(2) Uani 1 1 d . . .
C5 C 0.8373(11) 0.2789(3) 0.2926(6) 0.058(2) Uani 1 1 d . . .
H5 H 0.7748 0.2973 0.3255 0.070 Uiso 1 1 calc R . .
C6 C 0.9624(11) 0.2451(3) 0.3297(5) 0.052(2) Uani 1 1 d . . .
C7 C 0.6271(13) 0.3046(4) 0.1626(8) 0.086(3) Uani 1 1 d . . .
H7A H 0.6392 0.3201 0.1099 0.103 Uiso 1 1 calc R . .
H7B H 0.5879 0.3293 0.1979 0.103 Uiso 1 1 calc R . .
C8 C 0.4837(11) 0.2643(3) 0.1429(5) 0.061(2) Uani 1 1 d . . .
H8A H 0.3812 0.2736 0.1667 0.073 Uiso 1 1 calc R . .
H8B H 0.4416 0.2619 0.0817 0.073 Uiso 1 1 calc R . .
C9 C 0.5493(8) 0.2151(3) 0.1771(4) 0.0408(17) Uani 1 1 d . . .
C10 C 0.5421(10) 0.2023(2) 0.2593(4) 0.0410(17) Uani 1 1 d . . .
H10 H 0.4553 0.2165 0.2848 0.049 Uiso 1 1 calc R . .
C11 C 0.6598(9) 0.1695(2) 0.3030(4) 0.0388(16) Uani 1 1 d . . .
C12 C 0.7912(10) 0.1489(3) 0.2675(4) 0.0470(18) Uani 1 1 d . . .
C13 C 0.7722(9) 0.1546(3) 0.1826(4) 0.0446(18) Uani 1 1 d . . .
H13 H 0.8430 0.1360 0.1540 0.054 Uiso 1 1 calc R . .
C14 C 0.6535(10) 0.1865(3) 0.1390(4) 0.0480(19) Uani 1 1 d . . .
H14 H 0.6425 0.1891 0.0805 0.058 Uiso 1 1 calc R . .
C15 C 0.9723(10) 0.1326(3) 0.3206(5) 0.056(2) Uani 1 1 d . . .
H15A H 1.0026 0.1007 0.3015 0.067 Uiso 1 1 calc R . .
H15B H 0.9639 0.1299 0.3797 0.067 Uiso 1 1 calc R . .
C16 C 1.1236(11) 0.1696(3) 0.3131(6) 0.067(2) Uani 1 1 d . . .
H16A H 1.2066 0.1722 0.3680 0.081 Uiso 1 1 calc R . .
H16B H 1.1909 0.1569 0.2730 0.081 Uiso 1 1 calc R . .
C17 C 0.6521(10) 0.1620(3) 0.3945(4) 0.0438(17) Uani 1 1 d . . .
C18 C 0.5204(11) 0.0821(2) 0.3581(4) 0.0488(19) Uani 1 1 d . . .
H18A H 0.4992 0.0946 0.3004 0.059 Uiso 1 1 calc R . .
H18B H 0.4051 0.0714 0.3686 0.059 Uiso 1 1 calc R . .
C19 C 0.6415(15) 0.0399(3) 0.3650(6) 0.075(3) Uani 1 1 d . . .
H19A H 0.7498 0.0491 0.3471 0.113 Uiso 1 1 calc R . .
H19B H 0.5823 0.0139 0.3295 0.113 Uiso 1 1 calc R . .
H19C H 0.6719 0.0290 0.4231 0.113 Uiso 1 1 calc R . .
C20 C 0.5724(12) 0.1150(3) 0.5041(4) 0.057(2) Uani 1 1 d . . .
H20A H 0.5705 0.0805 0.5175 0.068 Uiso 1 1 calc R A 1
H20B H 0.6770 0.1294 0.5416 0.068 Uiso 1 1 calc R A 1
C21 C 0.416(2) 0.1370(5) 0.5189(8) 0.068(5) Uani 0.645(19) 1 d P B 1
H21A H 0.3979 0.1272 0.5737 0.102 Uiso 0.645(19) 1 calc PR B 1
H21B H 0.3144 0.1270 0.4757 0.102 Uiso 0.645(19) 1 calc PR B 1
H21C H 0.4287 0.1719 0.5174 0.102 Uiso 0.645(19) 1 calc PR B 1
C21' C 0.761(3) 0.1106(7) 0.5541(16) 0.063(8) Uani 0.355(19) 1 d P B 2
H21D H 0.8419 0.1266 0.5242 0.094 Uiso 0.355(19) 1 calc PR B 2
H21E H 0.7932 0.0766 0.5615 0.094 Uiso 0.355(19) 1 calc PR B 2
H21F H 0.7709 0.1256 0.6088 0.094 Uiso 0.355(19) 1 calc PR B 2
N1 N 0.5893(8) 0.12075(19) 0.4160(3) 0.0440(14) Uani 1 1 d . B .
O1 O 0.9847(9) 0.2358(2) 0.4146(4) 0.0782(19) Uani 1 1 d . . .
H1 H 0.8974 0.2201 0.4230 0.117 Uiso 1 1 calc R . .
O2 O 0.6999(9) 0.19478(19) 0.4458(3) 0.0665(17) Uani 1 1 d . . .
C22 C 0.9289(11) 0.4664(3) 0.5151(5) 0.059(2) Uani 1 1 d . . .
C23 C 0.9883(13) 0.4791(4) 0.5949(6) 0.074(3) Uani 1 1 d . . .
H23 H 1.0965 0.4654 0.6244 0.088 Uiso 1 1 calc R . .
C24 C 0.9045(15) 0.5096(4) 0.6353(6) 0.075(3) Uani 1 1 d . . .
H24 H 0.9535 0.5162 0.6924 0.090 Uiso 1 1 calc R . .
C25 C 0.7495(17) 0.5320(4) 0.5972(7) 0.080(3) Uani 1 1 d . . .
C26 C 0.7046(9) 0.5267(2) 0.5107(6) 0.056(2) Uani 1 1 d . . .
H26 H 0.6105 0.5452 0.4791 0.067 Uiso 1 1 calc R . .
C27 C 0.7951(11) 0.4951(3) 0.4702(5) 0.056(2) Uani 1 1 d . . .
C28 C 0.6067(18) 0.5481(4) 0.6414(10) 0.126(5) Uani 1 1 d . . .
H28A H 0.5359 0.5736 0.6078 0.152 Uiso 1 1 calc R . .
H28B H 0.6642 0.5623 0.6958 0.152 Uiso 1 1 calc R . .
C29 C 0.4776(13) 0.5073(3) 0.6572(6) 0.062(2) Uani 1 1 d . . .
H29A H 0.4905 0.5028 0.7180 0.075 Uiso 1 1 calc R . .
H29B H 0.3538 0.5171 0.6337 0.075 Uiso 1 1 calc R . .
C30 C 0.5134(10) 0.4610(2) 0.6191(4) 0.0436(18) Uani 1 1 d . . .
C31 C 0.6539(10) 0.4316(3) 0.6574(4) 0.0494(19) Uani 1 1 d . . .
H31 H 0.6952 0.4336 0.7161 0.059 Uiso 1 1 calc R . .
C32 C 0.7342(10) 0.4002(3) 0.6134(5) 0.052(2) Uani 1 1 d . . .
H32 H 0.8279 0.3805 0.6422 0.062 Uiso 1 1 calc R . .
C33 C 0.6792(9) 0.3966(2) 0.5248(4) 0.0402(17) Uani 1 1 d . . .
C34 C 0.5163(8) 0.4160(2) 0.4917(4) 0.0354(16) Uani 1 1 d . . .
C35 C 0.4351(8) 0.4485(3) 0.5362(4) 0.0408(17) Uani 1 1 d . . .
H35 H 0.3249 0.4624 0.5101 0.049 Uiso 1 1 calc R . .
C36 C 0.8122(10) 0.3815(3) 0.4754(5) 0.0526(19) Uani 1 1 d . . .
H36A H 0.7523 0.3789 0.4159 0.063 Uiso 1 1 calc R . .
H36B H 0.8585 0.3494 0.4945 0.063 Uiso 1 1 calc R . .
C37 C 0.9665(14) 0.4163(3) 0.4837(7) 0.079(3) Uani 1 1 d . . .
H37A H 0.9979 0.4197 0.4286 0.095 Uiso 1 1 calc R . .
H37B H 1.0704 0.4025 0.5226 0.095 Uiso 1 1 calc R . .
C38 C 0.4292(10) 0.4097(2) 0.3998(4) 0.0446(18) Uani 1 1 d . . .
C39 C 0.2468(12) 0.3630(3) 0.2892(4) 0.060(2) Uani 1 1 d . . .
H39A H 0.3267 0.3737 0.2532 0.072 Uiso 1 1 calc R . .
H39B H 0.2221 0.3285 0.2784 0.072 Uiso 1 1 calc R . .
C40 C 0.0817(16) 0.3898(3) 0.2682(6) 0.087(3) Uani 1 1 d . . .
H40A H -0.0005 0.3778 0.3013 0.130 Uiso 1 1 calc R . .
H40B H 0.0289 0.3858 0.2088 0.130 Uiso 1 1 calc R . .
H40C H 0.1055 0.4238 0.2805 0.130 Uiso 1 1 calc R . .
C41 C 0.3017(10) 0.3332(2) 0.4360(4) 0.0443(18) Uani 1 1 d . . .
H41A H 0.1756 0.3237 0.4201 0.053 Uiso 1 1 calc R . .
H41B H 0.3230 0.3469 0.4929 0.053 Uiso 1 1 calc R . .
C42 C 0.4172(13) 0.2892(2) 0.4366(5) 0.065(2) Uani 1 1 d . . .
H42A H 0.4006 0.2764 0.3799 0.097 Uiso 1 1 calc R . .
H42B H 0.3838 0.2649 0.4733 0.097 Uiso 1 1 calc R . .
H42C H 0.5417 0.2980 0.4570 0.097 Uiso 1 1 calc R . .
N2 N 0.3363(8) 0.36985(18) 0.3785(3) 0.0402(14) Uani 1 1 d . . .
O3 O 0.7417(11) 0.4864(3) 0.3847(3) 0.098(3) Uani 1 1 d . . .
H3A H 0.6342 0.4787 0.3733 0.147 Uiso 1 1 calc R . .
O4 O 0.4441(8) 0.44101(19) 0.3482(3) 0.0722(19) 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 C6 1.368(11) . ?
C1 C2 1.404(11) . ?
C1 C16 1.482(11) . ?
C2 C3 1.395(12) . ?
C3 C4 1.369(12) . ?
C4 C5 1.385(12) . ?
C4 C7 1.515(14) . ?
C5 C6 1.393(11) . ?
C6 O1 1.392(10) . ?
C7 C8 1.564(13) . ?
C8 C9 1.529(11) . ?
C9 C14 1.376(10) . ?
C9 C10 1.410(9) . ?
C10 C11 1.379(9) . ?
C11 C12 1.400(10) . ?
C11 C17 1.531(9) . ?
C12 C13 1.380(10) . ?
C12 C15 1.549(11) . ?
C13 C14 1.366(10) . ?
C15 C16 1.585(12) . ?
C17 O2 1.245(8) . ?
C17 N1 1.328(8) . ?
C18 N1 1.462(8) . ?
C18 C19 1.493(12) . ?
C20 C21 1.421(17) . ?
C20 N1 1.490(9) . ?
C20 C21' 1.52(3) . ?
C22 C23 1.339(12) . ?
C22 C27 1.388(12) . ?
C22 C37 1.541(12) . ?
C23 C24 1.332(14) . ?
C24 C25 1.376(16) . ?
C25 C26 1.396(13) . ?
C25 C28 1.516(16) . ?
C26 C27 1.384(11) . ?
C27 O3 1.396(10) . ?
C28 C29 1.574(15) . ?
C29 C30 1.488(10) . ?
C30 C31 1.397(10) . ?
C30 C35 1.410(10) . ?
C31 C32 1.368(11) . ?
C32 C33 1.429(10) . ?
C33 C34 1.371(9) . ?
C33 C36 1.502(11) . ?
C34 C35 1.396(9) . ?
C34 C38 1.525(9) . ?
C36 C37 1.521(12) . ?
C38 O4 1.239(8) . ?
C38 N2 1.330(8) . ?
C39 C40 1.455(14) . ?
C39 N2 1.493(8) . ?
C41 N2 1.456(8) . ?
C41 C42 1.518(11) . ?
 
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
C6 C1 C2 115.5(7) . . ?
C6 C1 C16 122.1(7) . . ?
C2 C1 C16 120.1(8) . . ?
C3 C2 C1 120.9(8) . . ?
C4 C3 C2 120.4(8) . . ?
C3 C4 C5 117.6(8) . . ?
C3 C4 C7 123.4(9) . . ?
C5 C4 C7 118.5(8) . . ?
C4 C5 C6 118.9(7) . . ?
C1 C6 O1 117.4(7) . . ?
C1 C6 C5 123.1(7) . . ?
O1 C6 C5 119.3(7) . . ?
C4 C7 C8 111.8(8) . . ?
C9 C8 C7 114.0(7) . . ?
C14 C9 C10 115.9(6) . . ?
C14 C9 C8 122.3(6) . . ?
C10 C9 C8 120.0(6) . . ?
C11 C10 C9 120.6(6) . . ?
C10 C11 C12 120.9(6) . . ?
C10 C11 C17 116.2(6) . . ?
C12 C11 C17 122.6(6) . . ?
C13 C12 C11 116.5(6) . . ?
C13 C12 C15 119.3(7) . . ?
C11 C12 C15 122.3(6) . . ?
C14 C13 C12 121.2(6) . . ?
C13 C14 C9 122.2(6) . . ?
C12 C15 C16 110.9(6) . . ?
C1 C16 C15 114.3(6) . . ?
O2 C17 N1 122.0(6) . . ?
O2 C17 C11 119.7(6) . . ?
N1 C17 C11 118.3(6) . . ?
N1 C18 C19 113.5(7) . . ?
C21 C20 N1 112.1(8) . . ?
C21 C20 C21' 134.2(12) . . ?
N1 C20 C21' 104.9(11) . . ?
C17 N1 C18 124.8(5) . . ?
C17 N1 C20 117.8(5) . . ?
C18 N1 C20 117.2(6) . . ?
C23 C22 C27 115.3(9) . . ?
C23 C22 C37 121.2(9) . . ?
C27 C22 C37 121.2(8) . . ?
C24 C23 C22 123.8(10) . . ?
C23 C24 C25 122.3(9) . . ?
C24 C25 C26 114.6(9) . . ?
C24 C25 C28 124.8(12) . . ?
C26 C25 C28 118.2(12) . . ?
C27 C26 C25 121.1(8) . . ?
C26 C27 C22 120.6(8) . . ?
C26 C27 O3 121.5(8) . . ?
C22 C27 O3 117.4(8) . . ?
C25 C28 C29 114.6(8) . . ?
C30 C29 C28 112.2(7) . . ?
C31 C30 C35 114.8(6) . . ?
C31 C30 C29 121.1(7) . . ?
C35 C30 C29 122.8(7) . . ?
C32 C31 C30 122.4(7) . . ?
C31 C32 C33 120.9(7) . . ?
C34 C33 C32 115.0(7) . . ?
C34 C33 C36 125.0(6) . . ?
C32 C33 C36 118.8(6) . . ?
C33 C34 C35 121.8(6) . . ?
C33 C34 C38 121.3(6) . . ?
C35 C34 C38 116.2(6) . . ?
C34 C35 C30 121.3(6) . . ?
C33 C36 C37 112.8(6) . . ?
C36 C37 C22 114.1(7) . . ?
O4 C38 N2 122.3(6) . . ?
O4 C38 C34 120.6(6) . . ?
N2 C38 C34 117.0(6) . . ?
C40 C39 N2 111.4(7) . . ?
N2 C41 C42 112.5(6) . . ?
C38 N2 C41 125.6(5) . . ?
C38 N2 C39 118.4(5) . . ?
C41 N2 C39 115.9(5) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              25.99
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.520
_refine_diff_density_min   -0.430
_refine_diff_density_rms    0.104
