# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 188/259 
 
data_rajxtsx 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 2,2'-Biadamantane
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C20 H30' 
_chemical_formula_weight          270.44 
_chemical_melting_point           ? 
_chemical_compound_source         'chemical synthesis' 
 
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' 
 
_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    C2/c
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
 
_cell_length_a                    9.2428(5) 
_cell_length_b                    9.0959(11) 
_cell_length_c                    18.4539(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  103.6340(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1507.7(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     4247 
_cell_measurement_theta_min       3 
_cell_measurement_theta_max       28 
 
_exptl_crystal_description        'prism' 
_exptl_crystal_colour             'colorless'
_exptl_crystal_size_max           0.4 
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.191 
_exptl_crystal_density_method     none 
_exptl_crystal_F_000              600 
_exptl_absorpt_coefficient_mu     0.066 
_exptl_absorpt_correction_type    'Semi-empirical (SADABS procedure)' 
_exptl_absorpt_correction_T_min   0.87 
_exptl_absorpt_correction_T_max   0.93
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Siemens SMART 1K' 
_diffrn_measurement_method        
;
\w-scan, frame range 0.3 deg, hemisphere
; 
_diffrn_standards_number          201 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0.5 
_diffrn_reflns_number             10681 
_diffrn_reflns_av_R_equivalents   0.0215 
_diffrn_reflns_av_sigmaI/netI     0.0161 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        29 
_diffrn_reflns_theta_min          2.27 
_diffrn_reflns_theta_max          35.49 
_reflns_number_total              3308 
_reflns_number_observed           2493 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'SMART V5.054 (BruckerAXS, 1997-98)'
_computing_cell_refinement        'SAINT V6.01 (BruckerAXS, 1997-99)'
_computing_data_reduction         'SAINT & SADABS (Sheldrick, 1998)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'XP V5.06 (Siemens, 1996)'
_computing_publication_material   'SHELXL-93 & XCIF V5.05 (Siemens, 1996)'
 
_refine_special_details 
; 
 Refinement on F^2^ for all reflections except for 14 with very negative F^2^ 
 or flagged by us for potential systematic errors. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.1621P] 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     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3294 
_refine_ls_number_parameters      151 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0539 
_refine_ls_R_factor_obs           0.0390 
_refine_ls_wR_factor_all          0.1349 
_refine_ls_wR_factor_obs          0.1039 
_refine_ls_goodness_of_fit_all    1.053 
_refine_ls_goodness_of_fit_obs    1.100 
_refine_ls_restrained_S_all       1.238 
_refine_ls_restrained_S_obs       1.100 
_refine_ls_shift/esd_max          0.002 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
C1 C 0.29822(5) 0.20798(5) -0.02227(2) 0.01514(11) Uani 1 d . . 
C2 C 0.20604(6) 0.11143(6) -0.08558(3) 0.01760(11) Uani 1 d . . 
C3 C 0.31131(7) 0.01805(6) -0.12008(3) 0.02211(12) Uani 1 d . . 
C4 C 0.41249(6) 0.11788(6) -0.15359(3) 0.02069(12) Uani 1 d . . 
C5 C 0.50356(6) 0.21524(7) -0.09143(3) 0.02152(12) Uani 1 d . . 
C6 C 0.39873(6) 0.30925(6) -0.05687(3) 0.01785(11) Uani 1 d . . 
C7 C 0.11019(6) 0.20757(7) -0.14686(3) 0.02124(12) Uani 1 d . . 
C8 C 0.21090(6) 0.30918(7) -0.18001(3) 0.02226(12) Uani 1 d . . 
C9 C 0.30374(6) 0.40667(6) -0.11814(3) 0.02197(12) Uani 1 d . . 
C10 C 0.31619(7) 0.21523(7) -0.21420(3) 0.02378(13) Uani 1 d . . 
H1 H 0.3695(9) 0.1384(9) 0.0112(4) 0.032(2) Uiso 1 d . . 
H2 H 0.1400(9) 0.0420(10) -0.0644(5) 0.035(2) Uiso 1 d . . 
H3A H 0.3738(10) -0.0453(11) -0.0820(5) 0.044(2) Uiso 1 d . . 
H3B H 0.2535(10) -0.0465(10) -0.1583(5) 0.041(2) Uiso 1 d . . 
H4 H 0.4819(10) 0.0563(10) -0.1769(5) 0.035(2) Uiso 1 d . . 
H5A H 0.5718(10) 0.2821(10) -0.1120(5) 0.037(2) Uiso 1 d . . 
H5B H 0.5685(10) 0.1548(10) -0.0527(5) 0.038(2) Uiso 1 d . . 
H6 H 0.4608(10) 0.3736(10) -0.0181(5) 0.036(2) Uiso 1 d . . 
H7A H 0.0352(10) 0.2667(10) -0.1276(5) 0.037(2) Uiso 1 d . . 
H7B H 0.0525(10) 0.1437(10) -0.1860(5) 0.039(2) Uiso 1 d . . 
H8 H 0.1485(10) 0.3754(10) -0.2187(5) 0.040(2) Uiso 1 d . . 
H9A H 0.3699(10) 0.4752(10) -0.1399(5) 0.043(2) Uiso 1 d . . 
H9B H 0.2389(9) 0.4747(10) -0.0964(5) 0.037(2) Uiso 1 d . . 
H10A H 0.2572(10) 0.1529(11) -0.2551(5) 0.043(2) Uiso 1 d . . 
H10B H 0.3816(10) 0.2817(9) -0.2360(5) 0.038(2) Uiso 1 d . . 
 
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 0.0161(2) 0.0164(2) 0.0129(2) -0.00082(14) 0.0035(2) 0.00055(15) 
C2 0.0205(2) 0.0184(2) 0.0146(2) -0.0029(2) 0.0054(2) -0.0028(2) 
C3 0.0296(3) 0.0194(2) 0.0192(2) -0.0037(2) 0.0092(2) 0.0002(2) 
C4 0.0216(2) 0.0244(3) 0.0173(2) -0.0018(2) 0.0070(2) 0.0036(2) 
C5 0.0166(2) 0.0281(3) 0.0207(2) -0.0020(2) 0.0062(2) 0.0020(2) 
C6 0.0164(2) 0.0199(2) 0.0180(2) -0.0023(2) 0.0054(2) -0.0020(2) 
C7 0.0167(2) 0.0315(3) 0.0149(2) -0.0021(2) 0.0025(2) -0.0007(2) 
C8 0.0220(2) 0.0293(3) 0.0160(2) 0.0055(2) 0.0055(2) 0.0060(2) 
C9 0.0248(3) 0.0190(2) 0.0251(2) 0.0041(2) 0.0118(2) 0.0018(2) 
C10 0.0245(3) 0.0330(3) 0.0156(2) 0.0018(2) 0.0082(2) 0.0039(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 1.5468(7) . ? 
C1 C6 1.5489(7) . ? 
C1 C1 1.5492(9) 7 ? 
C1 H1 1.013(8) . ? 
C2 C7 1.5350(7) . ? 
C2 C3 1.5381(7) . ? 
C2 H2 1.018(9) . ? 
C3 C4 1.5343(8) . ? 
C3 H3A 0.984(9) . ? 
C3 H3B 0.975(9) . ? 
C4 C5 1.5341(8) . ? 
C4 C10 1.5356(8) . ? 
C4 H4 1.020(9) . ? 
C5 C6 1.5388(7) . ? 
C5 H5A 1.011(9) . ? 
C5 H5B 0.985(9) . ? 
C6 C9 1.5383(7) . ? 
C6 H6 0.995(9) . ? 
C7 C8 1.5374(8) . ? 
C7 H7A 1.006(9) . ? 
C7 H7B 0.981(9) . ? 
C8 C9 1.5377(8) . ? 
C8 C10 1.5378(8) . ? 
C8 H8 1.006(9) . ? 
C9 H9A 1.019(10) . ? 
C9 H9B 1.008(9) . ? 
C10 H10A 0.997(9) . ? 
C10 H10B 1.004(9) . ? 
 
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 107.66(4) . . ? 
C2 C1 C1 113.42(5) . 7 ? 
C6 C1 C1 113.66(5) . 7 ? 
C2 C1 H1 105.6(5) . . ? 
C6 C1 H1 104.9(5) . . ? 
C1 C1 H1 111.0(5) 7 . ? 
C7 C2 C3 108.73(4) . . ? 
C7 C2 C1 110.64(4) . . ? 
C3 C2 C1 109.67(4) . . ? 
C7 C2 H2 110.0(5) . . ? 
C3 C2 H2 108.1(5) . . ? 
C1 C2 H2 109.6(5) . . ? 
C4 C3 C2 110.19(5) . . ? 
C4 C3 H3A 108.9(5) . . ? 
C2 C3 H3A 110.5(5) . . ? 
C4 C3 H3B 110.3(5) . . ? 
C2 C3 H3B 109.9(5) . . ? 
H3A C3 H3B 107.1(8) . . ? 
C5 C4 C3 108.63(4) . . ? 
C5 C4 C10 109.48(5) . . ? 
C3 C4 C10 109.34(4) . . ? 
C5 C4 H4 110.1(5) . . ? 
C3 C4 H4 110.4(5) . . ? 
C10 C4 H4 108.9(5) . . ? 
C4 C5 C6 110.03(4) . . ? 
C4 C5 H5A 110.3(5) . . ? 
C6 C5 H5A 109.3(5) . . ? 
C4 C5 H5B 110.7(5) . . ? 
C6 C5 H5B 110.2(5) . . ? 
H5A C5 H5B 106.3(7) . . ? 
C9 C6 C5 108.76(4) . . ? 
C9 C6 C1 110.59(4) . . ? 
C5 C6 C1 109.75(5) . . ? 
C9 C6 H6 108.8(5) . . ? 
C5 C6 H6 108.2(5) . . ? 
C1 C6 H6 110.7(5) . . ? 
C2 C7 C8 109.71(4) . . ? 
C2 C7 H7A 111.7(5) . . ? 
C8 C7 H7A 110.6(5) . . ? 
C2 C7 H7B 108.9(5) . . ? 
C8 C7 H7B 109.7(5) . . ? 
H7A C7 H7B 106.1(7) . . ? 
C7 C8 C9 109.60(4) . . ? 
C7 C8 C10 109.28(5) . . ? 
C9 C8 C10 109.19(4) . . ? 
C7 C8 H8 110.1(5) . . ? 
C9 C8 H8 108.0(5) . . ? 
C10 C8 H8 110.7(5) . . ? 
C8 C9 C6 109.60(4) . . ? 
C8 C9 H9A 110.0(5) . . ? 
C6 C9 H9A 110.5(5) . . ? 
C8 C9 H9B 111.7(5) . . ? 
C6 C9 H9B 110.6(5) . . ? 
H9A C9 H9B 104.4(8) . . ? 
C4 C10 C8 109.62(4) . . ? 
C4 C10 H10A 110.0(5) . . ? 
C8 C10 H10A 109.9(6) . . ? 
C4 C10 H10B 109.8(5) . . ? 
C8 C10 H10B 109.2(5) . . ? 
H10A C10 H10B 108.3(7) . . ? 
 
_refine_diff_density_max    0.321 
_refine_diff_density_min   -0.294 
_refine_diff_density_rms    0.058