 
data_2008src0988
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C23 H26 N2 O2'
_chemical_formula_weight          362.46
 
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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.4658(2)
_cell_length_b                    12.1791(4)
_cell_length_c                    15.8842(5)
_cell_angle_alpha                 106.312(2)
_cell_angle_beta                  99.182(2)
_cell_angle_gamma                 102.509(2)
_cell_volume                      962.93(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8315
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.43
_exptl_crystal_size_mid           0.11
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.250
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              388
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9664
_exptl_absorpt_correction_T_max   0.9936
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'  
 
_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 Roper 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             19642
_diffrn_reflns_av_R_equivalents   0.0733
_diffrn_reflns_av_sigmaI/netI     0.0689
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.43
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4394
_reflns_number_gt                 2915
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 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, R.W.W., 1998)' 
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0541P)²+0.1586P] 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        0.034(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4394
_refine_ls_number_parameters      245
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0896
_refine_ls_R_factor_gt            0.0505
_refine_ls_wR_factor_ref          0.1299
_refine_ls_wR_factor_gt           0.1130
_refine_ls_goodness_of_fit_ref    1.053
_refine_ls_restrained_S_all       1.053
_refine_ls_shift/su_max           0.001
_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 0.1507(3) -0.07501(14) 0.10562(11) 0.0188(4) Uani 1 1 d . . .
C2 C 0.2260(3) -0.08162(15) 0.02438(11) 0.0206(4) Uani 1 1 d . . .
H2 H 0.2646 -0.0117 0.0079 0.025 Uiso 1 1 calc R . .
C3 C 0.2456(3) -0.18671(15) -0.03232(11) 0.0231(4) Uani 1 1 d . . .
H3 H 0.2943 -0.1895 -0.0875 0.028 Uiso 1 1 calc R . .
C4 C 0.1929(3) -0.28814(15) -0.00735(11) 0.0234(4) Uani 1 1 d . . .
H4 H 0.2111 -0.3605 -0.0447 0.028 Uiso 1 1 calc R . .
C5 C 0.1140(3) -0.28442(15) 0.07172(11) 0.0220(4) Uani 1 1 d . . .
H5 H 0.0757 -0.3550 0.0873 0.026 Uiso 1 1 calc R . .
C6 C 0.0896(3) -0.17881(14) 0.12915(10) 0.0180(4) Uani 1 1 d . . .
C8 C -0.1508(3) -0.12001(14) 0.24646(11) 0.0213(4) Uani 1 1 d . . .
C9 C -0.2255(3) -0.03424(15) 0.20129(11) 0.0215(4) Uani 1 1 d . . .
H9A H -0.3013 -0.0773 0.1362 0.026 Uiso 1 1 calc R . .
H9B H -0.3586 -0.0028 0.2277 0.026 Uiso 1 1 calc R . .
C11 C 0.1791(3) 0.04842(14) 0.16643(11) 0.0187(4) Uani 1 1 d . . .
C12 C 0.0664(3) -0.27149(15) 0.25037(11) 0.0217(4) Uani 1 1 d . . .
H12A H 0.0987 -0.2381 0.3169 0.026 Uiso 1 1 calc R . .
H12B H 0.2252 -0.2903 0.2358 0.026 Uiso 1 1 calc R . .
C13 C -0.1513(3) -0.38581(15) 0.21732(11) 0.0203(4) Uani 1 1 d . . .
C14 C -0.3726(3) -0.40429(15) 0.15225(12) 0.0236(4) Uani 1 1 d . . .
H14 H -0.3890 -0.3442 0.1261 0.028 Uiso 1 1 calc R . .
C15 C -0.5696(3) -0.50907(16) 0.12498(12) 0.0277(4) Uani 1 1 d . . .
H15 H -0.7182 -0.5204 0.0799 0.033 Uiso 1 1 calc R . .
C16 C -0.5520(3) -0.59717(16) 0.16275(12) 0.0264(4) Uani 1 1 d . . .
H16 H -0.6886 -0.6683 0.1446 0.032 Uiso 1 1 calc R . .
C17 C -0.3327(4) -0.58042(16) 0.22736(12) 0.0274(4) Uani 1 1 d . . .
H17 H -0.3187 -0.6405 0.2538 0.033 Uiso 1 1 calc R . .
C18 C -0.1331(3) -0.47658(15) 0.25381(11) 0.0240(4) Uani 1 1 d . . .
H18 H 0.0179 -0.4670 0.2973 0.029 Uiso 1 1 calc R . .
C19 C 0.0130(3) 0.18225(15) 0.27377(11) 0.0225(4) Uani 1 1 d . . .
H19A H -0.1573 0.1982 0.2626 0.027 Uiso 1 1 calc R . .
H19B H 0.1376 0.2429 0.2598 0.027 Uiso 1 1 calc R . .
C20 C 0.0963(3) 0.19694(15) 0.37371(11) 0.0234(4) Uani 1 1 d . . .
H20 H -0.0430 0.1439 0.3896 0.028 Uiso 1 1 calc R . .
C21 C 0.3472(4) 0.16417(18) 0.39719(12) 0.0305(4) Uani 1 1 d . . .
H21A H 0.4849 0.2123 0.3783 0.037 Uiso 1 1 calc R . .
H21B H 0.3230 0.0792 0.3638 0.037 Uiso 1 1 calc R . .
C22 C 0.4294(4) 0.1863(2) 0.49878(13) 0.0406(5) Uani 1 1 d . . .
H22A H 0.2993 0.1325 0.5165 0.049 Uiso 1 1 calc R . .
H22B H 0.5959 0.1677 0.5124 0.049 Uiso 1 1 calc R . .
C23 C 0.4575(4) 0.3148(2) 0.55340(14) 0.0434(6) Uani 1 1 d . . .
H23A H 0.6014 0.3680 0.5409 0.052 Uiso 1 1 calc R . .
H23B H 0.4997 0.3248 0.6186 0.052 Uiso 1 1 calc R . .
C24 C 0.2102(4) 0.3500(2) 0.53024(13) 0.0407(5) Uani 1 1 d . . .
H24A H 0.2391 0.4357 0.5627 0.049 Uiso 1 1 calc R . .
H24B H 0.0719 0.3044 0.5505 0.049 Uiso 1 1 calc R . .
C25 C 0.1245(4) 0.32594(17) 0.42891(12) 0.0313(4) Uani 1 1 d . . .
H25A H 0.2523 0.3797 0.4103 0.038 Uiso 1 1 calc R . .
H25B H -0.0429 0.3440 0.4158 0.038 Uiso 1 1 calc R . .
N7 N 0.0143(3) -0.18080(12) 0.21098(9) 0.0186(3) Uani 1 1 d . . .
N10 N -0.0053(3) 0.06462(12) 0.21187(9) 0.0198(3) Uani 1 1 d . . .
O1 O 0.3671(2) 0.13031(10) 0.17241(8) 0.0247(3) Uani 1 1 d . . .
O2 O -0.2325(3) -0.13447(11) 0.31084(8) 0.0326(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 1.402(2) . ?
C1 C6 1.404(2) . ?
C1 C11 1.501(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9500 . ?
C6 N7 1.430(2) . ?
C8 O2 1.220(2) . ?
C8 N7 1.377(2) . ?
C8 C9 1.512(2) . ?
C9 N10 1.456(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 O1 1.2376(19) . ?
C11 N10 1.347(2) . ?
C12 N7 1.470(2) . ?
C12 C13 1.517(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.391(2) . ?
C13 C18 1.399(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N10 1.464(2) . ?
C19 C20 1.528(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(2) . ?
C20 C25 1.530(2) . ?
C20 H20 1.0000 . ?
C21 C22 1.533(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.522(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.527(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 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
C2 C1 C6 118.99(15) . . ?
C2 C1 C11 115.31(14) . . ?
C6 C1 C11 125.13(15) . . ?
C3 C2 C1 121.90(15) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.87(15) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.33(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.34(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.52(15) . . ?
C5 C6 N7 118.27(14) . . ?
C1 C6 N7 123.15(15) . . ?
O2 C8 N7 121.92(15) . . ?
O2 C8 C9 121.71(16) . . ?
N7 C8 C9 116.37(14) . . ?
N10 C9 C8 111.92(13) . . ?
N10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
N10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O1 C11 N10 122.98(15) . . ?
O1 C11 C1 119.37(15) . . ?
N10 C11 C1 117.64(14) . . ?
N7 C12 C13 113.69(13) . . ?
N7 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N7 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 117.92(15) . . ?
C14 C13 C12 122.62(14) . . ?
C18 C13 C12 119.46(14) . . ?
C15 C14 C13 120.96(16) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.65(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.14(16) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.44(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.86(16) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N10 C19 C20 114.63(13) . . ?
N10 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
N10 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 113.12(15) . . ?
C19 C20 C25 108.33(14) . . ?
C21 C20 C25 110.27(14) . . ?
C19 C20 H20 108.3 . . ?
C21 C20 H20 108.3 . . ?
C25 C20 H20 108.3 . . ?
C20 C21 C22 111.07(16) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 111.44(17) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 111.26(16) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 111.31(17) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C20 112.32(16) . . ?
C24 C25 H25A 109.1 . . ?
C20 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C20 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C8 N7 C6 124.13(13) . . ?
C8 N7 C12 115.60(13) . . ?
C6 N7 C12 118.90(14) . . ?
C11 N10 C9 120.92(14) . . ?
C11 N10 C19 120.52(14) . . ?
C9 N10 C19 118.55(14) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.222
_refine_diff_density_min   -0.262
_refine_diff_density_rms    0.054
