 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H25 N O2'
_chemical_formula_weight          359.45
 
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    P2(1)2(1)2(1)
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    8.2378(5)
_cell_length_b                    9.2872(5)
_cell_length_c                    25.4354(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1945.96(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     43935
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.227
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              768
_exptl_absorpt_coefficient_mu     0.077
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9551
_exptl_absorpt_correction_T_max   0.9923
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             13136
_diffrn_reflns_av_R_equivalents   0.0626
_diffrn_reflns_av_sigmaI/netI     0.0528
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -32
_diffrn_reflns_limit_l_max        32
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3904
_reflns_number_gt                 2664
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.1188P)²+0.1606P] 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_number_reflns          3904
_refine_ls_number_parameters      244
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0987
_refine_ls_R_factor_gt            0.0634
_refine_ls_wR_factor_ref          0.1938
_refine_ls_wR_factor_gt           0.1711
_refine_ls_goodness_of_fit_ref    1.019
_refine_ls_restrained_S_all       1.019
_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 0.1314(4) 0.1322(3) 0.83965(10) 0.0483(7) Uani 1 1 d . . .
C2 C 0.0866(4) 0.1160(4) 0.78478(12) 0.0652(9) Uani 1 1 d . . .
H2A H 0.1795 0.0740 0.7655 0.078 Uiso 1 1 calc R . .
H2B H 0.0651 0.2125 0.7698 0.078 Uiso 1 1 calc R . .
C3 C -0.0575(7) 0.0243(5) 0.77626(18) 0.1096(17) Uani 1 1 d . . .
H3A H -0.1511 0.0892 0.7705 0.132 Uiso 1 1 calc R . .
H3B H -0.0400 -0.0290 0.7430 0.132 Uiso 1 1 calc R . .
C4 C -0.1025(7) -0.0734(8) 0.8133(2) 0.137(3) Uani 1 1 d . . .
H4A H -0.0456 -0.1647 0.8053 0.164 Uiso 1 1 calc R . .
H4B H -0.2200 -0.0917 0.8088 0.164 Uiso 1 1 calc R . .
C5 C -0.0757(5) -0.0420(4) 0.86683(17) 0.0832(12) Uani 1 1 d . . .
H5A H -0.0504 -0.1332 0.8853 0.100 Uiso 1 1 calc R . .
H5B H -0.1781 -0.0043 0.8819 0.100 Uiso 1 1 calc R . .
C6 C 0.0527(4) 0.0603(3) 0.87817(12) 0.0550(8) Uani 1 1 d . . .
H6 H 0.0823 0.0773 0.9137 0.066 Uiso 1 1 calc R . .
C7 C 0.2601(4) 0.2362(3) 0.85275(10) 0.0472(7) Uani 1 1 d . . .
C8 C 0.4199(4) 0.0723(3) 0.91072(10) 0.0494(7) Uani 1 1 d . . .
C9 C 0.4117(4) -0.0469(3) 0.87170(11) 0.0495(7) Uani 1 1 d . . .
C10 C 0.4587(4) -0.0281(4) 0.82085(12) 0.0612(8) Uani 1 1 d . . .
H10 H 0.4944 0.0638 0.8092 0.073 Uiso 1 1 calc R . .
C11 C 0.4545(5) -0.1465(5) 0.78496(16) 0.0837(12) Uani 1 1 d . . .
H11 H 0.4777 -0.1337 0.7487 0.100 Uiso 1 1 calc R . .
C12 C 0.4150(6) -0.2819(5) 0.80532(18) 0.0856(12) Uani 1 1 d . . .
H12 H 0.4325 -0.3650 0.7843 0.103 Uiso 1 1 calc R . .
C13 C 0.3519(8) -0.2978(5) 0.85466(18) 0.1009(15) Uani 1 1 d . . .
H13 H 0.3005 -0.3853 0.8646 0.121 Uiso 1 1 calc R . .
C14 C 0.3638(5) -0.1840(3) 0.89045(14) 0.0668(9) Uani 1 1 d . . .
H14 H 0.3402 -0.1983 0.9266 0.080 Uiso 1 1 calc R . .
C15 C 0.4136(3) 0.3312(3) 0.92706(10) 0.0458(7) Uani 1 1 d . . .
C16 C 0.3048(4) 0.3833(4) 0.96373(10) 0.0548(8) Uani 1 1 d . . .
H16 H 0.2031 0.3372 0.9687 0.066 Uiso 1 1 calc R . .
C17 C 0.3452(4) 0.5026(4) 0.99292(11) 0.0643(9) Uani 1 1 d . . .
H17 H 0.2710 0.5410 1.0178 0.077 Uiso 1 1 calc R . .
C18 C 0.4948(4) 0.5657(4) 0.98554(11) 0.0614(9) Uani 1 1 d . . .
H18 H 0.5235 0.6468 1.0063 0.074 Uiso 1 1 calc R . .
C19 C 0.6044(4) 0.5148(3) 0.94891(11) 0.0529(7) Uani 1 1 d . . .
C20 C 0.7635(5) 0.5927(4) 0.94089(15) 0.0752(10) Uani 1 1 d . . .
H20A H 0.7411 0.6887 0.9257 0.090 Uiso 1 1 calc R . .
H20B H 0.8155 0.6076 0.9756 0.090 Uiso 1 1 calc R . .
C21 C 0.8790(6) 0.5153(8) 0.9060(2) 0.138(2) Uani 1 1 d . . .
H21A H 0.9530 0.5876 0.8904 0.166 Uiso 1 1 calc R . .
H21B H 0.9460 0.4512 0.9283 0.166 Uiso 1 1 calc R . .
C22 C 0.8149(6) 0.4324(6) 0.8650(2) 0.1101(17) Uani 1 1 d . . .
H22A H 0.9037 0.3730 0.8503 0.132 Uiso 1 1 calc R . .
H22B H 0.7785 0.4987 0.8369 0.132 Uiso 1 1 calc R . .
C23 C 0.6783(4) 0.3356(4) 0.87798(13) 0.0645(9) Uani 1 1 d . . .
H23A H 0.7227 0.2427 0.8905 0.077 Uiso 1 1 calc R . .
H23B H 0.6158 0.3163 0.8455 0.077 Uiso 1 1 calc R . .
C24 C 0.5650(3) 0.3932(3) 0.91877(10) 0.0463(7) Uani 1 1 d . . .
N1 N 0.3630(3) 0.2072(2) 0.89583(8) 0.0440(6) Uani 1 1 d . . .
O1 O 0.2735(3) 0.3498(2) 0.82910(8) 0.0684(7) Uani 1 1 d . . .
O2 O 0.4794(3) 0.0549(2) 0.95339(8) 0.0734(7) 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
C1 C6 1.351(4) . ?
C1 C2 1.451(4) . ?
C1 C7 1.472(4) . ?
C2 C3 1.477(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.360(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.410(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.451(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 0.9500 . ?
C7 O1 1.219(3) . ?
C7 N1 1.411(3) . ?
C8 O2 1.202(3) . ?
C8 N1 1.391(4) . ?
C8 C9 1.489(4) . ?
C9 C10 1.362(4) . ?
C9 C14 1.415(4) . ?
C10 C11 1.430(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 C24 1.389(4) . ?
C15 N1 1.460(3) . ?
C16 C17 1.374(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 C24 1.403(4) . ?
C19 C20 1.511(5) . ?
C20 C21 1.486(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.400(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.477(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.495(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 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
C6 C1 C2 121.6(3) . . ?
C6 C1 C7 120.4(2) . . ?
C2 C1 C7 118.0(3) . . ?
C1 C2 C3 113.9(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
C4 C3 H3B 107.3 . . ?
C2 C3 H3B 107.3 . . ?
H3A C3 H3B 106.9 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4A 107.5 . . ?
C5 C4 H4A 107.5 . . ?
C3 C4 H4B 107.5 . . ?
C5 C4 H4B 107.5 . . ?
H4A C4 H4B 107.0 . . ?
C4 C5 C6 116.2(4) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C1 C6 C5 122.0(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O1 C7 N1 119.6(3) . . ?
O1 C7 C1 121.4(3) . . ?
N1 C7 C1 118.9(2) . . ?
O2 C8 N1 120.3(3) . . ?
O2 C8 C9 121.4(3) . . ?
N1 C8 C9 118.3(2) . . ?
C10 C9 C14 121.0(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 117.2(3) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 118.7(3) . . ?
C13 C14 H14 120.7 . . ?
C9 C14 H14 120.7 . . ?
C16 C15 C24 122.7(3) . . ?
C16 C15 N1 117.3(3) . . ?
C24 C15 N1 120.0(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C24 119.5(3) . . ?
C18 C19 C20 119.7(3) . . ?
C24 C19 C20 120.8(3) . . ?
C21 C20 C19 113.9(3) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 118.0(4) . . ?
C22 C21 H21A 107.8 . . ?
C20 C21 H21A 107.8 . . ?
C22 C21 H21B 107.8 . . ?
C20 C21 H21B 107.8 . . ?
H21A C21 H21B 107.2 . . ?
C21 C22 C23 117.1(4) . . ?
C21 C22 H22A 108.0 . . ?
C23 C22 H22A 108.0 . . ?
C21 C22 H22B 108.0 . . ?
C23 C22 H22B 108.0 . . ?
H22A C22 H22B 107.3 . . ?
C22 C23 C24 114.4(3) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C15 C24 C19 117.3(3) . . ?
C15 C24 C23 121.1(3) . . ?
C19 C24 C23 121.5(3) . . ?
C8 N1 C7 125.9(2) . . ?
C8 N1 C15 117.8(2) . . ?
C7 N1 C15 116.3(2) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 C1 C2 C3 4.4(5) . . . . ?
C7 C1 C2 C3 -172.3(3) . . . . ?
C1 C2 C3 C4 -22.3(7) . . . . ?
C2 C3 C4 C5 33.1(9) . . . . ?
C3 C4 C5 C6 -24.2(9) . . . . ?
C2 C1 C6 C5 2.9(5) . . . . ?
C7 C1 C6 C5 179.5(3) . . . . ?
C4 C5 C6 C1 6.3(6) . . . . ?
C6 C1 C7 O1 -140.1(3) . . . . ?
C2 C1 C7 O1 36.6(4) . . . . ?
C6 C1 C7 N1 35.7(4) . . . . ?
C2 C1 C7 N1 -147.6(3) . . . . ?
O2 C8 C9 C10 -132.0(3) . . . . ?
N1 C8 C9 C10 45.4(4) . . . . ?
O2 C8 C9 C14 43.6(4) . . . . ?
N1 C8 C9 C14 -139.1(3) . . . . ?
C14 C9 C10 C11 2.3(5) . . . . ?
C8 C9 C10 C11 177.8(3) . . . . ?
C9 C10 C11 C12 -5.6(6) . . . . ?
C10 C11 C12 C13 12.7(7) . . . . ?
C11 C12 C13 C14 -16.1(7) . . . . ?
C12 C13 C14 C9 12.2(7) . . . . ?
C10 C9 C14 C13 -5.5(6) . . . . ?
C8 C9 C14 C13 178.8(4) . . . . ?
C24 C15 C16 C17 1.1(5) . . . . ?
N1 C15 C16 C17 -178.0(3) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C17 C18 C19 C24 -1.4(5) . . . . ?
C17 C18 C19 C20 177.2(3) . . . . ?
C18 C19 C20 C21 171.8(4) . . . . ?
C24 C19 C20 C21 -9.6(5) . . . . ?
C19 C20 C21 C22 32.7(7) . . . . ?
C20 C21 C22 C23 -46.5(8) . . . . ?
C21 C22 C23 C24 34.7(7) . . . . ?
C16 C15 C24 C19 -1.0(4) . . . . ?
N1 C15 C24 C19 178.1(2) . . . . ?
C16 C15 C24 C23 -178.8(3) . . . . ?
N1 C15 C24 C23 0.3(4) . . . . ?
C18 C19 C24 C15 1.1(4) . . . . ?
C20 C19 C24 C15 -177.5(3) . . . . ?
C18 C19 C24 C23 178.9(3) . . . . ?
C20 C19 C24 C23 0.4(4) . . . . ?
C22 C23 C24 C15 165.9(4) . . . . ?
C22 C23 C24 C19 -11.9(5) . . . . ?
O2 C8 N1 C7 -165.1(3) . . . . ?
C9 C8 N1 C7 17.6(4) . . . . ?
O2 C8 N1 C15 15.2(4) . . . . ?
C9 C8 N1 C15 -162.2(2) . . . . ?
O1 C7 N1 C8 -147.5(3) . . . . ?
C1 C7 N1 C8 36.6(4) . . . . ?
O1 C7 N1 C15 32.3(4) . . . . ?
C1 C7 N1 C15 -143.6(3) . . . . ?
C16 C15 N1 C8 -100.0(3) . . . . ?
C24 C15 N1 C8 80.9(3) . . . . ?
C16 C15 N1 C7 80.2(3) . . . . ?
C24 C15 N1 C7 -98.9(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.948
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.948
_refine_diff_density_max    0.277
_refine_diff_density_min   -0.213
_refine_diff_density_rms    0.051
