 
data_2009src0297
# Dr P J Murphy 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C27 H29 N3 O3' 
_chemical_formula_weight          443.53 
 
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    P2(1)/c
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    12.0632(15) 
_cell_length_b                    17.471(2) 
_cell_length_c                    11.7628(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  105.363(7) 
_cell_angle_gamma                 90.00 
_cell_volume                      2390.5(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     105747 
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       26.37
 
_exptl_crystal_description        Fragment 
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.232 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              944 
_exptl_absorpt_coefficient_mu     0.081 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9840 
_exptl_absorpt_correction_T_max   0.9976 
_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             45452 
_diffrn_reflns_av_R_equivalents   0.1872 
_diffrn_reflns_av_sigmaI/netI     0.1310 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -21 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.92 
_diffrn_reflns_theta_max          26.63 
_reflns_number_total              4937 
_reflns_number_gt                 2829 
_reflns_threshold_expression      >2sigma(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     'SHELXS-97 (Sheldrick, 1990)' 
_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)+(0.0459P)²+2.6476P] 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          4937 
_refine_ls_number_parameters      303 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1906 
_refine_ls_R_factor_gt            0.1086 
_refine_ls_wR_factor_ref          0.1953 
_refine_ls_wR_factor_gt           0.1678 
_refine_ls_goodness_of_fit_ref    1.113 
_refine_ls_restrained_S_all       1.113 
_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 
N1 N 0.1268(2) 0.37135(18) -0.2865(2) 0.0297(7) Uani 1 1 d . . . 
N2 N 0.0432(3) 0.25883(18) -0.3825(2) 0.0331(8) Uani 1 1 d . . . 
H2 H 0.0608 0.2147 -0.4094 0.040 Uiso 1 1 calc R . . 
N3 N 0.2303(3) 0.25906(18) -0.2552(2) 0.0329(8) Uani 1 1 d . . . 
O1 O 0.5351(3) 0.43640(19) -0.2508(3) 0.0603(9) Uani 1 1 d . . . 
O2 O 0.0522(3) 0.38714(16) 0.0077(2) 0.0462(8) Uani 1 1 d . . . 
O3 O 0.1914(2) 0.36788(14) -0.0778(2) 0.0336(7) Uani 1 1 d . . . 
C1 C 0.3119(3) 0.3206(2) -0.1947(3) 0.0334(9) Uani 1 1 d . . . 
C2 C 0.3901(3) 0.2948(2) -0.0762(3) 0.0417(11) Uani 1 1 d . . . 
H2A H 0.3431 0.2803 -0.0233 0.063 Uiso 1 1 calc R . . 
H2B H 0.4415 0.3369 -0.0409 0.063 Uiso 1 1 calc R . . 
H2C H 0.4359 0.2508 -0.0884 0.063 Uiso 1 1 calc R . . 
C3 C 0.3809(3) 0.3463(2) -0.2812(3) 0.0369(10) Uani 1 1 d . . . 
H3 H 0.3242 0.3538 -0.3595 0.044 Uiso 1 1 calc R . . 
C4 C 0.4686(3) 0.2880(3) -0.2993(4) 0.0494(12) Uani 1 1 d . . . 
H4A H 0.4968 0.3034 -0.3668 0.074 Uiso 1 1 calc R . . 
H4B H 0.4323 0.2375 -0.3145 0.074 Uiso 1 1 calc R . . 
H4C H 0.5331 0.2856 -0.2284 0.074 Uiso 1 1 calc R . . 
C5 C 0.4370(4) 0.4232(3) -0.2446(3) 0.0452(11) Uani 1 1 d . . . 
C6 C 0.3712(3) 0.4833(2) -0.2017(3) 0.0385(10) Uani 1 1 d . . . 
C7 C 0.4289(4) 0.5609(3) -0.1898(4) 0.0563(13) Uani 1 1 d . . . 
H7A H 0.4296 0.5798 -0.2680 0.084 Uiso 1 1 calc R . . 
H7B H 0.5080 0.5563 -0.1406 0.084 Uiso 1 1 calc R . . 
H7C H 0.3864 0.5968 -0.1531 0.084 Uiso 1 1 calc R . . 
C8 C 0.2700(3) 0.4660(2) -0.1789(3) 0.0350(10) Uani 1 1 d . . . 
C9 C 0.1926(3) 0.5228(2) -0.1364(3) 0.0350(10) Uani 1 1 d . . . 
C10 C 0.2517(4) 0.5520(2) -0.0112(3) 0.0475(12) Uani 1 1 d . . . 
H10A H 0.2723 0.5084 0.0426 0.071 Uiso 1 1 calc R . . 
H10B H 0.1990 0.5858 0.0158 0.071 Uiso 1 1 calc R . . 
H10C H 0.3213 0.5805 -0.0127 0.071 Uiso 1 1 calc R . . 
C11 C 0.1552(4) 0.5904(2) -0.2228(4) 0.0504(12) Uani 1 1 d . . . 
H11A H 0.2216 0.6232 -0.2203 0.076 Uiso 1 1 calc R . . 
H11B H 0.0956 0.6202 -0.2001 0.076 Uiso 1 1 calc R . . 
H11C H 0.1245 0.5706 -0.3030 0.076 Uiso 1 1 calc R . . 
C12 C 0.0804(3) 0.4827(2) -0.1298(3) 0.0348(10) Uani 1 1 d . . . 
H12A H 0.0359 0.5175 -0.0921 0.042 Uiso 1 1 calc R . . 
H12B H 0.0331 0.4715 -0.2106 0.042 Uiso 1 1 calc R . . 
C13 C 0.1039(4) 0.4101(2) -0.0613(3) 0.0357(10) Uani 1 1 d . . . 
C14 C 0.2268(3) 0.3844(2) -0.1884(3) 0.0324(9) Uani 1 1 d . . . 
C15 C 0.1298(3) 0.2988(2) -0.3080(3) 0.0302(9) Uani 1 1 d . . . 
C16 C -0.0725(3) 0.2830(2) -0.4196(3) 0.0348(10) Uani 1 1 d . . . 
C17 C -0.1249(3) 0.3220(2) -0.3457(4) 0.0400(10) Uani 1 1 d . . . 
H17 H -0.0814 0.3360 -0.2687 0.048 Uiso 1 1 calc R . . 
C18 C -0.2411(4) 0.3409(3) -0.3833(4) 0.0494(12) Uani 1 1 d . . . 
H18 H -0.2769 0.3678 -0.3324 0.059 Uiso 1 1 calc R . . 
C19 C -0.3037(4) 0.3202(3) -0.4949(4) 0.0581(14) Uani 1 1 d . . . 
H19 H -0.3831 0.3326 -0.5208 0.070 Uiso 1 1 calc R . . 
C20 C -0.2520(4) 0.2817(3) -0.5688(4) 0.0598(14) Uani 1 1 d . . . 
H20 H -0.2955 0.2681 -0.6459 0.072 Uiso 1 1 calc R . . 
C21 C -0.1361(4) 0.2626(3) -0.5310(3) 0.0437(11) Uani 1 1 d . . . 
H21 H -0.1008 0.2354 -0.5819 0.052 Uiso 1 1 calc R . . 
C22 C 0.2223(3) 0.1859(2) -0.1995(3) 0.0353(10) Uani 1 1 d . . . 
C23 C 0.1491(4) 0.1762(2) -0.1274(3) 0.0377(10) Uani 1 1 d . . . 
H23 H 0.1033 0.2179 -0.1146 0.045 Uiso 1 1 calc R . . 
C24 C 0.1420(4) 0.1068(3) -0.0742(3) 0.0439(11) Uani 1 1 d . . . 
H24 H 0.0910 0.1006 -0.0257 0.053 Uiso 1 1 calc R . . 
C25 C 0.2091(4) 0.0467(3) -0.0915(4) 0.0580(13) Uani 1 1 d . . . 
H25 H 0.2055 -0.0008 -0.0535 0.070 Uiso 1 1 calc R . . 
C26 C 0.2815(5) 0.0551(3) -0.1637(5) 0.0782(18) Uani 1 1 d . . . 
H26 H 0.3268 0.0130 -0.1762 0.094 Uiso 1 1 calc R . . 
C27 C 0.2888(4) 0.1250(3) -0.2185(5) 0.0629(14) Uani 1 1 d . . . 
H27 H 0.3387 0.1308 -0.2683 0.076 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 
N1 C15 1.295(5) . ? 
N1 C14 1.449(5) . ? 
N2 C15 1.364(5) . ? 
N2 C16 1.412(5) . ? 
N2 H2 0.8800 . ? 
N3 C15 1.393(5) . ? 
N3 C22 1.451(5) . ? 
N3 C1 1.503(5) . ? 
O1 C5 1.226(5) . ? 
O2 C13 1.215(4) . ? 
O3 C13 1.344(4) . ? 
O3 C14 1.500(4) . ? 
C1 C14 1.530(5) . ? 
C1 C2 1.530(5) . ? 
C1 C3 1.542(5) . ? 
C2 H2A 0.9800 . ? 
C2 H2B 0.9800 . ? 
C2 H2C 0.9800 . ? 
C3 C5 1.515(6) . ? 
C3 C4 1.524(5) . ? 
C3 H3 1.0000 . ? 
C4 H4A 0.9800 . ? 
C4 H4B 0.9800 . ? 
C4 H4C 0.9800 . ? 
C5 C6 1.484(6) . ? 
C6 C8 1.351(5) . ? 
C6 C7 1.513(6) . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
C8 C14 1.512(5) . ? 
C8 C9 1.535(5) . ? 
C9 C10 1.543(5) . ? 
C9 C12 1.544(5) . ? 
C9 C11 1.546(5) . ? 
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 C13 1.489(5) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C16 C21 1.379(5) . ? 
C16 C17 1.383(5) . ? 
C17 C18 1.393(6) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.379(6) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.372(7) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.391(6) . ? 
C20 H20 0.9500 . ? 
C21 H21 0.9500 . ? 
C22 C27 1.385(6) . ? 
C22 C23 1.387(5) . ? 
C23 C24 1.378(6) . ? 
C23 H23 0.9500 . ? 
C24 C25 1.373(6) . ? 
C24 H24 0.9500 . ? 
C25 C26 1.378(7) . ? 
C25 H25 0.9500 . ? 
C26 C27 1.395(7) . ? 
C26 H26 0.9500 . ? 
C27 H27 0.9500 . ? 
 
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 
C15 N1 C14 104.4(3) . . ? 
C15 N2 C16 124.8(3) . . ? 
C15 N2 H2 117.6 . . ? 
C16 N2 H2 117.6 . . ? 
C15 N3 C22 119.1(3) . . ? 
C15 N3 C1 103.8(3) . . ? 
C22 N3 C1 122.0(3) . . ? 
C13 O3 C14 115.8(3) . . ? 
N3 C1 C14 100.4(3) . . ? 
N3 C1 C2 112.9(3) . . ? 
C14 C1 C2 115.5(3) . . ? 
N3 C1 C3 107.2(3) . . ? 
C14 C1 C3 107.8(3) . . ? 
C2 C1 C3 112.1(3) . . ? 
C1 C2 H2A 109.5 . . ? 
C1 C2 H2B 109.5 . . ? 
H2A C2 H2B 109.5 . . ? 
C1 C2 H2C 109.5 . . ? 
H2A C2 H2C 109.5 . . ? 
H2B C2 H2C 109.5 . . ? 
C5 C3 C4 111.0(3) . . ? 
C5 C3 C1 110.5(3) . . ? 
C4 C3 C1 114.5(3) . . ? 
C5 C3 H3 106.8 . . ? 
C4 C3 H3 106.8 . . ? 
C1 C3 H3 106.8 . . ? 
C3 C4 H4A 109.5 . . ? 
C3 C4 H4B 109.5 . . ? 
H4A C4 H4B 109.5 . . ? 
C3 C4 H4C 109.5 . . ? 
H4A C4 H4C 109.5 . . ? 
H4B C4 H4C 109.5 . . ? 
O1 C5 C6 119.9(4) . . ? 
O1 C5 C3 121.1(4) . . ? 
C6 C5 C3 119.0(4) . . ? 
C8 C6 C5 120.1(4) . . ? 
C8 C6 C7 126.9(4) . . ? 
C5 C6 C7 113.0(4) . . ? 
C6 C7 H7A 109.5 . . ? 
C6 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
C6 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
C6 C8 C14 120.6(4) . . ? 
C6 C8 C9 125.4(4) . . ? 
C14 C8 C9 114.0(3) . . ? 
C8 C9 C10 110.9(3) . . ? 
C8 C9 C12 109.9(3) . . ? 
C10 C9 C12 107.0(3) . . ? 
C8 C9 C11 112.1(3) . . ? 
C10 C9 C11 110.8(3) . . ? 
C12 C9 C11 105.8(3) . . ? 
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 . . ? 
C13 C12 C9 111.7(3) . . ? 
C13 C12 H12A 109.3 . . ? 
C9 C12 H12A 109.3 . . ? 
C13 C12 H12B 109.3 . . ? 
C9 C12 H12B 109.3 . . ? 
H12A C12 H12B 107.9 . . ? 
O2 C13 O3 118.5(4) . . ? 
O2 C13 C12 125.7(4) . . ? 
O3 C13 C12 115.7(3) . . ? 
N1 C14 O3 107.0(3) . . ? 
N1 C14 C8 113.9(3) . . ? 
O3 C14 C8 106.8(3) . . ? 
N1 C14 C1 105.9(3) . . ? 
O3 C14 C1 104.5(3) . . ? 
C8 C14 C1 117.9(3) . . ? 
N1 C15 N2 124.8(3) . . ? 
N1 C15 N3 117.8(3) . . ? 
N2 C15 N3 117.3(3) . . ? 
C21 C16 C17 119.5(4) . . ? 
C21 C16 N2 118.2(4) . . ? 
C17 C16 N2 122.2(3) . . ? 
C16 C17 C18 120.4(4) . . ? 
C16 C17 H17 119.8 . . ? 
C18 C17 H17 119.8 . . ? 
C19 C18 C17 119.5(4) . . ? 
C19 C18 H18 120.3 . . ? 
C17 C18 H18 120.3 . . ? 
C20 C19 C18 120.3(4) . . ? 
C20 C19 H19 119.8 . . ? 
C18 C19 H19 119.8 . . ? 
C19 C20 C21 120.1(4) . . ? 
C19 C20 H20 119.9 . . ? 
C21 C20 H20 119.9 . . ? 
C16 C21 C20 120.1(4) . . ? 
C16 C21 H21 119.9 . . ? 
C20 C21 H21 119.9 . . ? 
C27 C22 C23 119.6(4) . . ? 
C27 C22 N3 119.5(4) . . ? 
C23 C22 N3 120.9(3) . . ? 
C24 C23 C22 120.8(4) . . ? 
C24 C23 H23 119.6 . . ? 
C22 C23 H23 119.6 . . ? 
C25 C24 C23 119.7(4) . . ? 
C25 C24 H24 120.1 . . ? 
C23 C24 H24 120.1 . . ? 
C24 C25 C26 120.3(5) . . ? 
C24 C25 H25 119.8 . . ? 
C26 C25 H25 119.8 . . ? 
C25 C26 C27 120.4(5) . . ? 
C25 C26 H26 119.8 . . ? 
C27 C26 H26 119.8 . . ? 
C22 C27 C26 119.2(4) . . ? 
C22 C27 H27 120.4 . . ? 
C26 C27 H27 120.4 . . ? 
 
_diffrn_measured_fraction_theta_max    0.981 
_diffrn_reflns_theta_full              26.63 
_diffrn_measured_fraction_theta_full   0.981 
_refine_diff_density_max    0.203 
_refine_diff_density_min   -0.279 
_refine_diff_density_rms    0.053 
