# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


##Title:Synthesis of Polyhydroxylated Piperidines and their Analogues: 
##A novel approach for selective inhibitors of alpha- glucosidase
##Communicated to J.Org. Chemistry
##By Ganesh Pandey, Kishor C. Bharadwaj, M. Islam Khan, 
##K. S. Shashidhara and Vedavati G. Puranik
##Division of Organic Chemistry, Division of Biochemical Sciences
##and Centre For Materials Characterisation
##National Chemical Laboratory Pune 411 008, India.
 
data_Compound18b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             'diols'
_chemical_melting_point           '152-154 degree centigrade'  
_chemical_formula_moiety          'C16 H23 N O4'  
_chemical_formula_sum 
 'C16 H23 N O4' 
_chemical_formula_weight          293.35 
 
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    'P21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    10.9255(6) 
_cell_length_b                    5.6715(3) 
_cell_length_c                    12.9037(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.1430(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      764.04(8) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     '3775'
_cell_measurement_theta_min       '2.905' 
_cell_measurement_theta_max       '28.126' 
 
_exptl_crystal_description        'needle' 
_exptl_crystal_colour             colourless' 
_exptl_crystal_size_max           0.21 
_exptl_crystal_size_mid           0.05 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.275 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              316 
_exptl_absorpt_coefficient_mu     0.091 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9809 
_exptl_absorpt_correction_T_max   0.9981 
_exptl_absorpt_process_details    'Bruker SADABS'  
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD Area Detector'
_diffrn_measurement_device        'Bruker Smart APEX'  
_diffrn_measurement_method        'Omega Scan'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             5981 
_diffrn_reflns_av_R_equivalents   0.0439 
_diffrn_reflns_av_sigmaI/netI     0.0473 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.65 
_diffrn_reflns_theta_max          23.99 
_reflns_number_total              2186 
_reflns_number_gt                 2057 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'BRUKER SMART' 
_computing_cell_refinement        'BRUKER SAINT'  
_computing_data_reduction         'BRUKER SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'SHELXTL and PLATON' 
_computing_publication_material   'SHELXTL' 
 
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+0.8495P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     riding 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0(2) 
_refine_ls_number_reflns          2186 
_refine_ls_number_parameters      194 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0607 
_refine_ls_R_factor_gt            0.0565 
_refine_ls_wR_factor_ref          0.1156 
_refine_ls_wR_factor_gt           0.1142 
_refine_ls_goodness_of_fit_ref    1.175 
_refine_ls_restrained_S_all       1.175 
_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 
O1 O 0.3181(2) 0.8253(5) 0.22366(19) 0.0333(7) Uani 1 1 d . . . 
C2 C 0.2541(4) 0.9766(8) 0.1337(3) 0.0356(10) Uani 1 1 d . . . 
C3A C 0.4706(4) 0.9872(8) 0.1576(3) 0.0338(10) Uani 1 1 d . . . 
H3A H 0.4912 1.1136 0.2118 0.041 Uiso 1 1 calc R . . 
O3 O 0.3490(3) 1.0357(5) 0.0800(2) 0.0434(8) Uani 1 1 d . . . 
C4 C 0.5841(4) 0.9479(8) 0.1146(3) 0.0380(11) Uani 1 1 d . . . 
H4A H 0.5669 0.8201 0.0623 0.046 Uiso 1 1 calc R . . 
H4B H 0.6029 1.0895 0.0800 0.046 Uiso 1 1 calc R . . 
N5 N 0.6911(3) 0.8879(6) 0.2101(2) 0.0349(9) Uani 1 1 d . . . 
C6 C 0.6652(4) 0.6756(8) 0.2661(3) 0.0344(10) Uani 1 1 d . . . 
H6A H 0.7400 0.6414 0.3267 0.041 Uiso 1 1 calc R . . 
H6B H 0.6521 0.5432 0.2164 0.041 Uiso 1 1 calc R . . 
C7 C 0.5476(4) 0.6975(7) 0.3085(3) 0.0295(9) Uani 1 1 d . . . 
C7A C 0.4399(4) 0.7665(7) 0.2090(3) 0.0291(10) Uani 1 1 d . . . 
H7A H 0.4270 0.6382 0.1560 0.035 Uiso 1 1 calc R . . 
C8 C 0.5689(4) 0.8690(8) 0.4015(3) 0.0368(10) Uani 1 1 d . . . 
H8A H 0.6432 0.8197 0.4597 0.044 Uiso 1 1 calc R . . 
H8B H 0.5868 1.0238 0.3775 0.044 Uiso 1 1 calc R . . 
C9 C 0.2093(5) 1.1917(9) 0.1790(4) 0.0590(14) Uani 1 1 d . . . 
H9A H 0.1537 1.1458 0.2209 0.088 Uiso 1 1 calc R . . 
H9B H 0.1635 1.2924 0.1206 0.088 Uiso 1 1 calc R . . 
H9C H 0.2818 1.2748 0.2245 0.088 Uiso 1 1 calc R . . 
C10 C 0.1476(4) 0.8435(10) 0.0544(3) 0.0574(14) Uani 1 1 d . . . 
H10A H 0.1811 0.7011 0.0330 0.086 Uiso 1 1 calc R . . 
H10B H 0.1113 0.9396 -0.0084 0.086 Uiso 1 1 calc R . . 
H10C H 0.0826 0.8050 0.0880 0.086 Uiso 1 1 calc R . . 
C11 C 0.8097(4) 0.8598(11) 0.1800(3) 0.0499(13) Uani 1 1 d . . . 
H11A H 0.8167 0.9892 0.1329 0.060 Uiso 1 1 calc R . . 
H11B H 0.8045 0.7148 0.1390 0.060 Uiso 1 1 calc R . . 
C12 C 0.9298(4) 0.8532(9) 0.2760(3) 0.0374(10) Uani 1 1 d . . . 
C13 C 0.9551(4) 1.0335(8) 0.3503(3) 0.0436(12) Uani 1 1 d . . . 
H13 H 0.8964 1.1559 0.3426 0.052 Uiso 1 1 calc R . . 
C14 C 1.0666(4) 1.0360(9) 0.4365(4) 0.0493(12) Uani 1 1 d . . . 
H14 H 1.0826 1.1587 0.4865 0.059 Uiso 1 1 calc R . . 
C15 C 1.1533(4) 0.8545(9) 0.4471(4) 0.0495(12) Uani 1 1 d . . . 
H15 H 1.2287 0.8556 0.5043 0.059 Uiso 1 1 calc R . . 
C16 C 1.1294(5) 0.6727(10) 0.3740(4) 0.0511(13) Uani 1 1 d . . . 
H16 H 1.1880 0.5502 0.3817 0.061 Uiso 1 1 calc R . . 
C17 C 1.0172(4) 0.6726(9) 0.2887(4) 0.0423(11) Uani 1 1 d . . . 
H17 H 1.0007 0.5488 0.2392 0.051 Uiso 1 1 calc R . . 
O2 O 0.5234(3) 0.4650(5) 0.3413(2) 0.0387(7) Uani 1 1 d . . . 
H2 H 0.5188 0.4690 0.4035 0.058 Uiso 1 1 calc R . . 
O4 O 0.4614(3) 0.8844(6) 0.4417(2) 0.0505(9) Uani 1 1 d . . . 
H4 H 0.3972 0.9152 0.3917 0.076 Uiso 1 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0288(16) 0.0418(18) 0.0296(13) 0.0094(14) 0.0091(12) 0.0052(14) 
C2 0.023(2) 0.046(3) 0.035(2) 0.012(2) 0.0041(18) -0.002(2) 
C3A 0.030(3) 0.042(3) 0.0259(19) 0.006(2) 0.0021(18) 0.002(2) 
O3 0.0309(18) 0.062(2) 0.0336(15) 0.0216(15) 0.0035(13) 0.0029(16) 
C4 0.030(3) 0.055(3) 0.025(2) 0.007(2) 0.0014(19) -0.002(2) 
N5 0.027(2) 0.049(2) 0.0269(16) 0.0070(16) 0.0059(15) 0.0000(17) 
C6 0.032(3) 0.040(2) 0.028(2) -0.0001(19) 0.0027(19) 0.007(2) 
C7 0.036(3) 0.027(2) 0.025(2) 0.0034(17) 0.0067(18) 0.0030(19) 
C7A 0.037(3) 0.030(2) 0.0210(18) -0.0002(16) 0.0083(18) -0.0021(18) 
C8 0.040(3) 0.039(3) 0.029(2) -0.002(2) 0.0055(18) -0.005(2) 
C9 0.054(3) 0.051(3) 0.075(4) 0.010(3) 0.023(3) 0.014(3) 
C10 0.043(3) 0.076(4) 0.045(3) 0.015(3) 0.001(2) -0.008(3) 
C11 0.038(3) 0.080(4) 0.032(2) 0.004(3) 0.011(2) -0.002(3) 
C12 0.031(2) 0.050(3) 0.035(2) 0.000(2) 0.0157(19) 0.001(2) 
C13 0.035(3) 0.046(3) 0.050(3) 0.004(2) 0.012(2) 0.009(2) 
C14 0.047(3) 0.051(3) 0.049(3) -0.013(2) 0.012(2) -0.006(3) 
C15 0.034(3) 0.066(4) 0.047(3) 0.003(3) 0.009(2) -0.001(3) 
C16 0.043(3) 0.053(3) 0.060(3) 0.007(3) 0.017(3) 0.015(3) 
C17 0.037(3) 0.048(3) 0.043(3) -0.005(2) 0.014(2) 0.000(2) 
O2 0.060(2) 0.0268(15) 0.0289(14) 0.0026(12) 0.0126(14) -0.0008(14) 
O4 0.053(2) 0.066(2) 0.0329(15) -0.0125(17) 0.0133(14) 0.0000(19) 
 
_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 
O1 C7A 1.437(5) . ? 
O1 C2 1.447(4) . ? 
C2 O3 1.446(4) . ? 
C2 C9 1.496(6) . ? 
C2 C10 1.506(6) . ? 
C3A O3 1.436(5) . ? 
C3A C7A 1.500(5) . ? 
C3A C4 1.516(5) . ? 
C3A H3A 0.9800 . ? 
C4 N5 1.467(5) . ? 
C4 H4A 0.9700 . ? 
C4 H4B 0.9700 . ? 
N5 C11 1.467(5) . ? 
N5 C6 1.474(5) . ? 
C6 C7 1.543(5) . ? 
C6 H6A 0.9700 . ? 
C6 H6B 0.9700 . ? 
C7 O2 1.433(5) . ? 
C7 C8 1.508(5) . ? 
C7 C7A 1.515(5) . ? 
C7A H7A 0.9800 . ? 
C8 O4 1.420(5) . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C9 H9A 0.9600 . ? 
C9 H9B 0.9600 . ? 
C9 H9C 0.9600 . ? 
C10 H10A 0.9600 . ? 
C10 H10B 0.9600 . ? 
C10 H10C 0.9600 . ? 
C11 C12 1.517(5) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C13 1.372(6) . ? 
C12 C17 1.376(6) . ? 
C13 C14 1.387(6) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.378(7) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.369(7) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.386(6) . ? 
C16 H16 0.9300 . ? 
C17 H17 0.9300 . ? 
O2 H2 0.8200 . ? 
O4 H4 0.8200 . ? 
 
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 
C7A O1 C2 106.2(3) . . ? 
O3 C2 O1 106.1(3) . . ? 
O3 C2 C9 111.2(4) . . ? 
O1 C2 C9 107.8(3) . . ? 
O3 C2 C10 108.1(3) . . ? 
O1 C2 C10 110.0(4) . . ? 
C9 C2 C10 113.4(4) . . ? 
O3 C3A C7A 100.7(3) . . ? 
O3 C3A C4 117.4(3) . . ? 
C7A C3A C4 110.7(4) . . ? 
O3 C3A H3A 109.2 . . ? 
C7A C3A H3A 109.2 . . ? 
C4 C3A H3A 109.2 . . ? 
C3A O3 C2 105.5(3) . . ? 
N5 C4 C3A 105.2(3) . . ? 
N5 C4 H4A 110.7 . . ? 
C3A C4 H4A 110.7 . . ? 
N5 C4 H4B 110.7 . . ? 
C3A C4 H4B 110.7 . . ? 
H4A C4 H4B 108.8 . . ? 
C4 N5 C11 110.5(3) . . ? 
C4 N5 C6 112.3(3) . . ? 
C11 N5 C6 110.7(4) . . ? 
N5 C6 C7 114.1(3) . . ? 
N5 C6 H6A 108.7 . . ? 
C7 C6 H6A 108.7 . . ? 
N5 C6 H6B 108.7 . . ? 
C7 C6 H6B 108.7 . . ? 
H6A C6 H6B 107.6 . . ? 
O2 C7 C8 110.9(3) . . ? 
O2 C7 C7A 108.8(3) . . ? 
C8 C7 C7A 114.0(3) . . ? 
O2 C7 C6 106.0(3) . . ? 
C8 C7 C6 112.6(3) . . ? 
C7A C7 C6 103.9(3) . . ? 
O1 C7A C3A 101.6(3) . . ? 
O1 C7A C7 117.8(3) . . ? 
C3A C7A C7 111.8(3) . . ? 
O1 C7A H7A 108.4 . . ? 
C3A C7A H7A 108.4 . . ? 
C7 C7A H7A 108.4 . . ? 
O4 C8 C7 112.3(3) . . ? 
O4 C8 H8A 109.1 . . ? 
C7 C8 H8A 109.1 . . ? 
O4 C8 H8B 109.1 . . ? 
C7 C8 H8B 109.1 . . ? 
H8A C8 H8B 107.9 . . ? 
C2 C9 H9A 109.5 . . ? 
C2 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C2 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C2 C10 H10A 109.5 . . ? 
C2 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C2 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
N5 C11 C12 113.9(3) . . ? 
N5 C11 H11A 108.8 . . ? 
C12 C11 H11A 108.8 . . ? 
N5 C11 H11B 108.8 . . ? 
C12 C11 H11B 108.8 . . ? 
H11A C11 H11B 107.7 . . ? 
C13 C12 C17 118.8(4) . . ? 
C13 C12 C11 120.0(4) . . ? 
C17 C12 C11 121.2(4) . . ? 
C12 C13 C14 121.1(4) . . ? 
C12 C13 H13 119.5 . . ? 
C14 C13 H13 119.5 . . ? 
C15 C14 C13 119.2(5) . . ? 
C15 C14 H14 120.4 . . ? 
C13 C14 H14 120.4 . . ? 
C16 C15 C14 120.6(4) . . ? 
C16 C15 H15 119.7 . . ? 
C14 C15 H15 119.7 . . ? 
C15 C16 C17 119.5(5) . . ? 
C15 C16 H16 120.3 . . ? 
C17 C16 H16 120.3 . . ? 
C12 C17 C16 120.9(5) . . ? 
C12 C17 H17 119.5 . . ? 
C16 C17 H17 119.5 . . ? 
C7 O2 H2 109.5 . . ? 
C8 O4 H4 109.5 . . ? 
 
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 
C7A O1 C2 O3 -9.9(4) . . . . ? 
C7A O1 C2 C9 -129.2(4) . . . . ? 
C7A O1 C2 C10 106.7(4) . . . . ? 
C7A C3A O3 C2 38.5(4) . . . . ? 
C4 C3A O3 C2 158.7(4) . . . . ? 
O1 C2 O3 C3A -18.7(4) . . . . ? 
C9 C2 O3 C3A 98.3(4) . . . . ? 
C10 C2 O3 C3A -136.6(4) . . . . ? 
O3 C3A C4 N5 -176.4(3) . . . . ? 
C7A C3A C4 N5 -61.6(4) . . . . ? 
C3A C4 N5 C11 -176.4(4) . . . . ? 
C3A C4 N5 C6 59.4(4) . . . . ? 
C4 N5 C6 C7 -60.4(4) . . . . ? 
C11 N5 C6 C7 175.5(3) . . . . ? 
N5 C6 C7 O2 169.4(3) . . . . ? 
N5 C6 C7 C8 -69.1(4) . . . . ? 
N5 C6 C7 C7A 54.8(4) . . . . ? 
C2 O1 C7A C3A 33.2(4) . . . . ? 
C2 O1 C7A C7 155.6(3) . . . . ? 
O3 C3A C7A O1 -44.0(3) . . . . ? 
C4 C3A C7A O1 -168.9(3) . . . . ? 
O3 C3A C7A C7 -170.5(3) . . . . ? 
C4 C3A C7A C7 64.6(4) . . . . ? 
O2 C7 C7A O1 73.7(4) . . . . ? 
C8 C7 C7A O1 -50.7(5) . . . . ? 
C6 C7 C7A O1 -173.6(3) . . . . ? 
O2 C7 C7A C3A -169.2(3) . . . . ? 
C8 C7 C7A C3A 66.4(4) . . . . ? 
C6 C7 C7A C3A -56.5(4) . . . . ? 
O2 C7 C8 O4 -60.0(5) . . . . ? 
C7A C7 C8 O4 63.3(5) . . . . ? 
C6 C7 C8 O4 -178.7(3) . . . . ? 
C4 N5 C11 C12 166.8(4) . . . . ? 
C6 N5 C11 C12 -68.1(5) . . . . ? 
N5 C11 C12 C13 -54.8(6) . . . . ? 
N5 C11 C12 C17 127.4(5) . . . . ? 
C17 C12 C13 C14 0.3(6) . . . . ? 
C11 C12 C13 C14 -177.5(4) . . . . ? 
C12 C13 C14 C15 0.3(7) . . . . ? 
C13 C14 C15 C16 -0.6(7) . . . . ? 
C14 C15 C16 C17 0.3(7) . . . . ? 
C13 C12 C17 C16 -0.6(7) . . . . ? 
C11 C12 C17 C16 177.2(4) . . . . ? 
C15 C16 C17 C12 0.3(7) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.927 
_diffrn_reflns_theta_full              23.99 
_diffrn_measured_fraction_theta_full   0.927 
_refine_diff_density_max    0.201 
_refine_diff_density_min   -0.224 
_refine_diff_density_rms    0.048