# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/464

data_global
# SUBMISSION DETAILS 
  
_publ_contact_author_name            'Dr A.J. Blake' 
_publ_contact_author_address
;
  School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England UK
;
_publ_contact_author_email         A.J.Blake@nottingham.ac.uk
_publ_contact_author_fax          '0115 951 3563'
_publ_contact_author_phone        '0115 951 3488'
_publ_requested_journal           'J. Chem. Soc., Perkin Trans. 1' 

#============================================================================== 
  
# TITLE AND AUTHOR LIST 
  
_publ_section_title 
;
  Cascade Radical Cyclisations leading to Steroid Ring Constructions ...
; 
  
loop_
        _publ_author_name
        _publ_author_address

 'Haydn M. Boehm et al.' 
; School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England  UK
; 


data_STERAC
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety         'C21 H30 O4' 
_chemical_formula_sum            'C21 H30 O4' 
_chemical_formula_weight          346.45 
 
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' 
 '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) 
 
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                    8.567(3) 
_cell_length_b                    12.272(14) 
_cell_length_c                    16.895(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1776(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     7583
_cell_measurement_theta_min        2.4
_cell_measurement_theta_max       25.0
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.296 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              752 
_exptl_absorpt_coefficient_mu     0.088 
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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  'Enraf Nonius FAST TV dtector'
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         none 
_diffrn_reflns_number             7583 
_diffrn_reflns_av_R_equivalents   0.158 
_diffrn_reflns_av_sigmaI/netI     0.395 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.41 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              2769 
_reflns_number_gt                 884 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        FAST
_computing_cell_refinement        FAST
_computing_data_reduction         ABSURD
_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 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^)+(0.00P)^2^+0.00P] 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     geom
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0065(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    'not reliably determined' 
_refine_ls_number_reflns          2769 
_refine_ls_number_parameters      227 
_refine_ls_number_restraints      74 
_refine_ls_R_factor_all           0.131 
_refine_ls_R_factor_gt            0.035 
_refine_ls_wR_factor_ref          0.0821 
_refine_ls_wR_factor_gt           0.0582 
_refine_ls_goodness_of_fit_ref    0.406 
_refine_ls_restrained_S_all       0.401 
_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_symetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.4929(5) 0.8504(3) 0.5525(2) 0.0267(12) Uani 1 1 d U . . 
H1A H 0.4101 0.7947 0.5464 0.032 Uiso 1 1 calc R . . 
H1B H 0.4412 0.9222 0.5576 0.032 Uiso 1 1 calc R . . 
C2 C 0.5931(5) 0.8508(3) 0.4783(3) 0.0327(13) Uani 1 1 d U . . 
H2A H 0.5286 0.8738 0.4327 0.039 Uiso 1 1 calc R . . 
H2B H 0.6307 0.7759 0.4679 0.039 Uiso 1 1 calc R . . 
C3 C 0.7338(5) 0.9274(3) 0.4858(2) 0.0303(13) Uani 1 1 d U . . 
H3A H 0.8071 0.9130 0.4417 0.036 Uiso 1 1 calc R . . 
H3B H 0.6976 1.0037 0.4811 0.036 Uiso 1 1 calc R . . 
O4 O 0.9615(4) 0.9020(2) 0.56590(17) 0.0355(9) Uani 1 1 d U . . 
C4 C 0.8182(6) 0.9139(3) 0.5627(3) 0.0249(12) Uani 1 1 d U . . 
C5 C 0.7150(5) 0.9151(3) 0.6347(2) 0.0211(11) Uani 1 1 d U . . 
H5 H 0.6612 0.9874 0.6350 0.025 Uiso 1 1 calc R . . 
C6 C 0.8068(5) 0.9079(3) 0.7122(2) 0.0253(12) Uani 1 1 d U . . 
H6A H 0.8602 0.8365 0.7156 0.030 Uiso 1 1 calc R . . 
H6B H 0.8871 0.9659 0.7137 0.030 Uiso 1 1 calc R . . 
C7 C 0.6953(5) 0.9212(3) 0.7820(2) 0.0243(12) Uani 1 1 d U . . 
H7A H 0.6517 0.9959 0.7810 0.029 Uiso 1 1 calc R . . 
H7B H 0.7553 0.9132 0.8318 0.029 Uiso 1 1 calc R . . 
C8 C 0.5589(5) 0.8387(3) 0.7828(2) 0.0211(11) Uani 1 1 d U . . 
C9 C 0.4740(5) 0.8420(3) 0.7019(2) 0.0187(10) Uani 1 1 d U . . 
H9 H 0.4330 0.9180 0.6972 0.022 Uiso 1 1 calc R . . 
C10 C 0.5840(5) 0.8270(3) 0.6286(3) 0.0203(11) Uani 1 1 d U . . 
C11 C 0.3296(5) 0.7696(3) 0.7014(2) 0.0246(11) Uani 1 1 d U . . 
H11A H 0.3605 0.6937 0.7136 0.030 Uiso 1 1 calc R . . 
H11B H 0.2825 0.7704 0.6479 0.030 Uiso 1 1 calc R . . 
C12 C 0.2090(5) 0.8079(3) 0.7617(2) 0.0272(12) Uani 1 1 d U . . 
H12A H 0.1585 0.8748 0.7413 0.033 Uiso 1 1 calc R . . 
H12B H 0.1272 0.7513 0.7666 0.033 Uiso 1 1 calc R . . 
C13 C 0.2743(5) 0.8317(3) 0.8439(2) 0.0222(11) Uani 1 1 d U . . 
C14 C 0.4405(5) 0.8796(3) 0.8473(2) 0.0218(11) Uani 1 1 d U . . 
H14 H 0.4313 0.9604 0.8417 0.026 Uiso 1 1 calc R . . 
C15 C 0.4955(5) 0.8552(3) 0.9345(2) 0.0301(13) Uani 1 1 d U . . 
H15A H 0.6098 0.8437 0.9365 0.036 Uiso 1 1 calc R . . 
H15B H 0.4682 0.9163 0.9701 0.036 Uiso 1 1 calc R . . 
C16 C 0.4088(5) 0.7514(3) 0.9588(2) 0.0299(13) Uani 1 1 d U . . 
H16A H 0.4809 0.6884 0.9587 0.036 Uiso 1 1 calc R . . 
H16B H 0.3649 0.7596 1.0127 0.036 Uiso 1 1 calc R . . 
O17 O 0.1881(4) 0.6587(2) 0.89933(16) 0.0293(8) Uani 1 1 d U . . 
C17 C 0.2800(5) 0.7340(3) 0.8998(2) 0.0235(12) Uani 1 1 d U . . 
C18 C 0.1610(6) 0.9109(3) 0.8871(3) 0.0367(14) Uani 1 1 d U . . 
H18A H 0.0546 0.8817 0.8848 0.055 Uiso 1 1 calc R . . 
H18B H 0.1641 0.9823 0.8613 0.055 Uiso 1 1 calc R . . 
H18C H 0.1930 0.9184 0.9425 0.055 Uiso 1 1 calc R . . 
C19 C 0.6536(5) 0.7120(3) 0.6236(2) 0.0292(13) Uani 1 1 d U . . 
H19A H 0.7230 0.7073 0.5776 0.044 Uiso 1 1 calc R . . 
H19B H 0.5692 0.6586 0.6180 0.044 Uiso 1 1 calc R . . 
H19C H 0.7130 0.6965 0.6718 0.044 Uiso 1 1 calc R . . 
O20 O 0.5257(3) 0.6470(2) 0.81049(18) 0.0304(9) Uani 1 1 d U . . 
C20 C 0.6121(5) 0.7244(4) 0.8070(2) 0.0207(11) Uani 1 1 d U . . 
O21 O 0.7646(3) 0.7186(2) 0.82652(15) 0.0237(8) Uani 1 1 d U . . 
C21 C 0.8192(5) 0.6094(3) 0.8463(2) 0.0337(14) Uani 1 1 d U . . 
H21A H 0.9304 0.6122 0.8598 0.051 Uiso 1 1 calc R . . 
H21B H 0.8039 0.5611 0.8008 0.051 Uiso 1 1 calc R . . 
H21C H 0.7601 0.5816 0.8917 0.051 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 
C1 0.024(3) 0.033(3) 0.023(3) 0.001(2) 0.001(2) 0.001(2) 
C2 0.038(4) 0.037(3) 0.023(3) 0.002(2) 0.002(2) -0.006(3) 
C3 0.036(3) 0.031(3) 0.024(3) -0.003(2) 0.010(2) 0.001(3) 
O4 0.031(2) 0.0380(18) 0.037(2) 0.0006(18) 0.0118(17) 0.0030(19) 
C4 0.030(3) 0.015(2) 0.029(3) -0.001(3) 0.007(2) 0.002(3) 
C5 0.020(3) 0.025(2) 0.018(3) 0.002(2) 0.004(2) -0.001(2) 
C6 0.029(3) 0.022(2) 0.025(3) 0.004(2) 0.001(2) -0.013(3) 
C7 0.030(3) 0.024(2) 0.019(3) 0.000(2) 0.002(2) 0.001(3) 
C8 0.023(3) 0.018(2) 0.022(3) 0.001(2) -0.004(2) -0.003(2) 
C9 0.019(3) 0.016(2) 0.021(3) 0.000(2) 0.000(2) -0.002(2) 
C10 0.022(3) 0.017(2) 0.021(3) -0.003(2) -0.002(2) -0.004(2) 
C11 0.022(3) 0.035(2) 0.016(3) 0.005(2) -0.006(2) -0.001(2) 
C12 0.018(3) 0.037(3) 0.027(3) 0.012(2) -0.003(2) -0.002(2) 
C13 0.025(3) 0.016(2) 0.025(3) 0.004(2) 0.003(2) 0.002(2) 
C14 0.023(3) 0.021(2) 0.021(3) -0.004(2) -0.002(2) -0.003(2) 
C15 0.043(4) 0.029(3) 0.019(3) -0.003(2) -0.003(2) -0.007(2) 
C16 0.042(4) 0.028(3) 0.020(3) 0.002(2) 0.003(2) 0.000(2) 
O17 0.026(2) 0.0270(16) 0.035(2) 0.0038(16) 0.0025(16) -0.0025(17) 
C17 0.028(3) 0.028(3) 0.014(3) -0.005(2) 0.003(2) 0.006(2) 
C18 0.035(3) 0.031(3) 0.044(4) 0.002(3) 0.008(3) 0.010(3) 
C19 0.033(3) 0.023(2) 0.031(3) 0.002(2) 0.000(2) -0.001(2) 
O20 0.023(2) 0.0234(16) 0.044(2) 0.0022(17) -0.0042(17) -0.0082(16) 
C20 0.022(3) 0.030(2) 0.011(3) -0.007(2) 0.002(2) 0.003(2) 
O21 0.023(2) 0.0198(15) 0.028(2) 0.0022(15) -0.0056(15) 0.0044(15) 
C21 0.033(3) 0.025(3) 0.043(4) 0.005(3) -0.007(3) 0.007(2) 
 
_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 
C1 C2 1.518(5) . ? 
C1 C10 1.532(5) . ? 
C2 C3 1.534(5) . ? 
C3 C4 1.496(6) . ? 
O4 C4 1.237(5) . ? 
C4 C5 1.504(5) . ? 
C5 C6 1.530(5) . ? 
C5 C10 1.562(5) . ? 
C6 C7 1.527(5) . ? 
C7 C8 1.546(5) . ? 
C8 C20 1.531(5) . ? 
C8 C9 1.550(5) . ? 
C8 C14 1.570(6) . ? 
C9 C11 1.522(5) . ? 
C9 C10 1.567(5) . ? 
C10 C19 1.534(5) . ? 
C11 C12 1.526(5) . ? 
C12 C13 1.525(5) . ? 
C13 C17 1.527(5) . ? 
C13 C14 1.542(5) . ? 
C13 C18 1.555(5) . ? 
C14 C15 1.576(5) . ? 
C15 C16 1.530(5) . ? 
C16 C17 1.502(5) . ? 
O17 C17 1.214(5) . ? 
O20 C20 1.205(5) . ? 
C20 O21 1.349(5) . ? 
O21 C21 1.458(4) . ? 
 
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 C10 113.9(4) . . ? 
C1 C2 C3 112.2(4) . . ? 
C4 C3 C2 112.5(4) . . ? 
O4 C4 C3 122.0(4) . . ? 
O4 C4 C5 123.4(5) . . ? 
C3 C4 C5 114.6(4) . . ? 
C4 C5 C6 112.9(4) . . ? 
C4 C5 C10 111.2(4) . . ? 
C6 C5 C10 112.7(4) . . ? 
C7 C6 C5 109.5(4) . . ? 
C6 C7 C8 114.2(3) . . ? 
C20 C8 C7 112.1(4) . . ? 
C20 C8 C9 113.5(3) . . ? 
C7 C8 C9 109.3(3) . . ? 
C20 C8 C14 107.4(3) . . ? 
C7 C8 C14 106.6(3) . . ? 
C9 C8 C14 107.5(4) . . ? 
C11 C9 C8 111.8(3) . . ? 
C11 C9 C10 114.6(3) . . ? 
C8 C9 C10 114.3(4) . . ? 
C1 C10 C19 108.9(3) . . ? 
C1 C10 C5 106.9(3) . . ? 
C19 C10 C5 111.2(4) . . ? 
C1 C10 C9 109.6(4) . . ? 
C19 C10 C9 112.7(4) . . ? 
C5 C10 C9 107.4(3) . . ? 
C9 C11 C12 111.5(3) . . ? 
C13 C12 C11 114.8(4) . . ? 
C12 C13 C17 115.1(3) . . ? 
C12 C13 C14 116.4(4) . . ? 
C17 C13 C14 104.3(4) . . ? 
C12 C13 C18 108.6(4) . . ? 
C17 C13 C18 102.8(3) . . ? 
C14 C13 C18 108.7(3) . . ? 
C13 C14 C8 116.7(3) . . ? 
C13 C14 C15 103.8(3) . . ? 
C8 C14 C15 113.3(4) . . ? 
C16 C15 C14 105.3(3) . . ? 
C17 C16 C15 107.3(4) . . ? 
O17 C17 C16 126.1(4) . . ? 
O17 C17 C13 124.9(4) . . ? 
C16 C17 C13 108.8(4) . . ? 
O20 C20 O21 122.8(4) . . ? 
O20 C20 C8 123.5(4) . . ? 
O21 C20 C8 113.7(4) . . ? 
C20 O21 C21 114.5(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.916 
_diffrn_reflns_theta_full              24.99 
_diffrn_measured_fraction_theta_full   0.916 
_refine_diff_density_max    0.13 
_refine_diff_density_min   -0.13 
_refine_diff_density_rms    0.03