 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C25 H31 N O3'
_chemical_formula_sum
 'C25 H31 N O3'
_chemical_formula_weight          393.51
_chemical_absolute_configuration  unk
 
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            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, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    7.8264(3)
_cell_length_b                    13.1709(6)
_cell_length_c                    20.7532(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2139.26(17)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     15719
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.222
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              848
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9540
_exptl_absorpt_correction_T_max   0.9937
_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             11808
_diffrn_reflns_av_R_equivalents   0.0486
_diffrn_reflns_av_sigmaI/netI     0.0476
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.03
_diffrn_reflns_theta_max          27.49
_reflns_number_total              2732
_reflns_number_gt                 2226
_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     'PLATON (Watkin, Pearce 1995)'
_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)+(0.0416P)²+0.0836P] 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
_refine_ls_number_reflns          2732
_refine_ls_number_parameters      269
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0581
_refine_ls_R_factor_gt            0.0403
_refine_ls_wR_factor_ref          0.0902
_refine_ls_wR_factor_gt           0.0847
_refine_ls_goodness_of_fit_ref    1.155
_refine_ls_restrained_S_all       1.155
_refine_ls_shift/su_max           0.018
_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 0.0903(3) 1.12603(18) 0.35336(10) 0.0298(6) Uani 1 1 d . . .
H1A H 0.1643 1.1465 0.3892 0.045 Uiso 1 1 calc R . .
H1B H 0.0276 1.0644 0.3652 0.045 Uiso 1 1 calc R . .
H1C H 0.0091 1.1807 0.3439 0.045 Uiso 1 1 calc R . .
C2 C 0.1982(3) 1.10533(17) 0.29441(10) 0.0220(5) Uani 1 1 d . . .
C3 C 0.2580(3) 1.00837(18) 0.28160(10) 0.0247(5) Uani 1 1 d . . .
H3 H 0.2247 0.9538 0.3087 0.030 Uiso 1 1 calc R . .
C4 C 0.3656(3) 0.98961(18) 0.22991(10) 0.0244(5) Uani 1 1 d . . .
H4 H 0.4033 0.9222 0.2220 0.029 Uiso 1 1 calc R . .
C5 C 0.4197(3) 1.06724(17) 0.18928(10) 0.0217(5) Uani 1 1 d . . .
C6 C 0.3535(2) 1.16348(18) 0.20014(10) 0.0236(5) Uani 1 1 d . . .
H6 H 0.3822 1.2174 0.1718 0.028 Uiso 1 1 calc R . .
C7 C 0.2451(3) 1.18186(17) 0.25230(10) 0.0248(5) Uani 1 1 d . . .
H7 H 0.2026 1.2486 0.2590 0.030 Uiso 1 1 calc R . .
C8 C 0.5487(3) 1.04231(17) 0.13558(9) 0.0209(5) Uani 1 1 d . . .
H8 H 0.5567 0.9666 0.1343 0.025 Uiso 1 1 calc R . .
C9 C 0.8486(3) 1.01093(17) 0.17424(10) 0.0254(5) Uani 1 1 d . . .
H9 H 0.9548 1.0518 0.1810 0.030 Uiso 1 1 calc R . .
C10 C 0.8978(3) 0.92321(18) 0.13023(11) 0.0307(5) Uani 1 1 d . . .
H10A H 0.7999 0.8775 0.1252 0.046 Uiso 1 1 calc R . .
H10B H 0.9937 0.8859 0.1492 0.046 Uiso 1 1 calc R . .
H10C H 0.9314 0.9498 0.0880 0.046 Uiso 1 1 calc R . .
C11 C 0.7963(3) 0.97068(17) 0.24082(11) 0.0284(5) Uani 1 1 d . . .
H11A H 0.7610 1.0275 0.2682 0.043 Uiso 1 1 calc R . .
H11B H 0.8936 0.9358 0.2607 0.043 Uiso 1 1 calc R . .
H11C H 0.7010 0.9230 0.2361 0.043 Uiso 1 1 calc R . .
C12 C 0.7524(3) 1.18838(16) 0.15249(11) 0.0245(5) Uani 1 1 d . . .
H12 H 0.6499 1.2244 0.1350 0.029 Uiso 1 1 calc R . .
C13 C 0.7712(3) 1.22042(17) 0.22335(10) 0.0279(5) Uani 1 1 d . . .
H13A H 0.6701 1.1987 0.2476 0.042 Uiso 1 1 calc R . .
H13B H 0.7821 1.2944 0.2259 0.042 Uiso 1 1 calc R . .
H13C H 0.8733 1.1886 0.2418 0.042 Uiso 1 1 calc R . .
C14 C 0.9072(3) 1.22527(19) 0.11371(11) 0.0288(5) Uani 1 1 d . . .
H14A H 1.0110 1.1926 0.1301 0.043 Uiso 1 1 calc R . .
H14B H 0.9179 1.2991 0.1181 0.043 Uiso 1 1 calc R . .
H14C H 0.8917 1.2077 0.0682 0.043 Uiso 1 1 calc R . .
C15 C 0.4779(3) 1.07451(17) 0.06929(10) 0.0224(5) Uani 1 1 d . . .
H15 H 0.4667 1.1501 0.0679 0.027 Uiso 1 1 calc R . .
C16 C 0.5973(3) 1.04003(16) 0.01636(10) 0.0215(5) Uani 1 1 d . . .
C17 C 0.6862(3) 1.10014(17) -0.02334(10) 0.0231(5) Uani 1 1 d . . .
H17 H 0.6679 1.1714 -0.0217 0.028 Uiso 1 1 calc R . .
C19 C 0.8099(3) 1.05990(17) -0.06887(10) 0.0241(5) Uani 1 1 d . . .
C20 C 0.8178(3) 0.94799(17) -0.06992(10) 0.0228(5) Uani 1 1 d . . .
C21 C 0.9236(3) 0.89463(19) -0.11258(10) 0.0272(5) Uani 1 1 d . . .
H21 H 0.9963 0.9312 -0.1410 0.033 Uiso 1 1 calc R . .
C22 C 0.9238(3) 0.7905(2) -0.11403(10) 0.0296(5) Uani 1 1 d . . .
H22 H 0.9958 0.7556 -0.1435 0.036 Uiso 1 1 calc R . .
C23 C 0.8183(3) 0.73569(18) -0.07217(10) 0.0272(5) Uani 1 1 d . . .
H23 H 0.8188 0.6636 -0.0733 0.033 Uiso 1 1 calc R . .
C24 C 0.7134(3) 0.78592(17) -0.02933(10) 0.0246(5) Uani 1 1 d . . .
H24 H 0.6420 0.7491 -0.0006 0.030 Uiso 1 1 calc R . .
C25 C 0.7144(3) 0.89170(16) -0.02900(9) 0.0210(5) Uani 1 1 d . . .
C26 C 0.2236(3) 1.06370(19) 0.00702(11) 0.0326(6) Uani 1 1 d . . .
H26A H 0.2105 1.1376 0.0088 0.049 Uiso 1 1 calc R . .
H26B H 0.1105 1.0317 0.0059 0.049 Uiso 1 1 calc R . .
H26C H 0.2875 1.0451 -0.0318 0.049 Uiso 1 1 calc R . .
N1 N 0.7247(2) 1.07897(13) 0.14236(8) 0.0203(4) Uani 1 1 d . . .
O1 O 0.31425(19) 1.02968(12) 0.06266(7) 0.0274(4) Uani 1 1 d . . .
O2 O 0.9034(2) 1.11403(13) -0.10249(8) 0.0359(4) Uani 1 1 d . . .
O3 O 0.60577(18) 0.93696(11) 0.01489(6) 0.0224(3) 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 C2 1.511(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.384(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C8 1.540(3) . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.466(3) . ?
C8 C15 1.542(3) . ?
C8 H8 1.0000 . ?
C9 N1 1.477(3) . ?
C9 C10 1.522(3) . ?
C9 C11 1.535(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.472(3) . ?
C12 C14 1.534(3) . ?
C12 C13 1.537(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O1 1.417(3) . ?
C15 C16 1.512(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.338(3) . ?
C16 O3 1.359(3) . ?
C17 C19 1.453(3) . ?
C17 H17 0.9500 . ?
C19 O2 1.237(3) . ?
C19 C20 1.475(3) . ?
C20 C25 1.388(3) . ?
C20 C21 1.401(3) . ?
C21 C22 1.371(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.400(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(3) . ?
C24 H24 0.9500 . ?
C25 O3 1.381(2) . ?
C26 O1 1.427(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.41(19) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 120.7(2) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.34(19) . . ?
C6 C5 C8 123.87(19) . . ?
C4 C5 C8 118.79(19) . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 121.6(2) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N1 C8 C5 118.46(17) . . ?
N1 C8 C15 109.42(17) . . ?
C5 C8 C15 110.56(17) . . ?
N1 C8 H8 105.8 . . ?
C5 C8 H8 105.8 . . ?
C15 C8 H8 105.8 . . ?
N1 C9 C10 110.97(17) . . ?
N1 C9 C11 115.93(17) . . ?
C10 C9 C11 110.20(19) . . ?
N1 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C11 C9 H9 106.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C14 110.59(18) . . ?
N1 C12 C13 114.79(18) . . ?
C14 C12 C13 109.86(18) . . ?
N1 C12 H12 107.1 . . ?
C14 C12 H12 107.1 . . ?
C13 C12 H12 107.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C16 111.28(17) . . ?
O1 C15 C8 107.26(17) . . ?
C16 C15 C8 110.08(17) . . ?
O1 C15 H15 109.4 . . ?
C16 C15 H15 109.4 . . ?
C8 C15 H15 109.4 . . ?
C17 C16 O3 123.5(2) . . ?
C17 C16 C15 126.2(2) . . ?
O3 C16 C15 110.26(18) . . ?
C16 C17 C19 122.1(2) . . ?
C16 C17 H17 119.0 . . ?
C19 C17 H17 119.0 . . ?
O2 C19 C17 123.4(2) . . ?
O2 C19 C20 122.9(2) . . ?
C17 C19 C20 113.70(19) . . ?
C25 C20 C21 117.6(2) . . ?
C25 C20 C19 120.0(2) . . ?
C21 C20 C19 122.4(2) . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 118.7(2) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
O3 C25 C20 122.13(19) . . ?
O3 C25 C24 115.58(18) . . ?
C20 C25 C24 122.3(2) . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 N1 C12 118.34(17) . . ?
C8 N1 C9 117.39(17) . . ?
C12 N1 C9 115.66(17) . . ?
C15 O1 C26 113.40(16) . . ?
C16 O3 C25 118.41(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.980
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.980
_refine_diff_density_max    0.191
_refine_diff_density_min   -0.194
_refine_diff_density_rms    0.043
