# Supplementary Material (ESI) for Perkin Transactions # This journal is (c) The Royal Society of Chemistry 2000 # CCDC Number: 207/488 data_fm39 _audit_creation_method SHELXL _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 '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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.851(2) _cell_length_b 17.570(4) _cell_length_c 11.462(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.59 _cell_angle_gamma 90.00(7) _cell_volume 1341.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description unknown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.573 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device unknown _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 4745 _diffrn_reflns_av_R_equivalents 0.1234 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 22.55 _reflns_number_total 1519 _reflns_number_observed 1369 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan: PROCESS (MSC)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'texsan' _computing_publication_material 'teXsan: FINISH (MSC)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.5337P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0381(61) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1518 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_obs 0.0465 _refine_ls_wR_factor_all 0.1494 _refine_ls_wR_factor_obs 0.1238 _refine_ls_goodness_of_fit_all 1.053 _refine_ls_goodness_of_fit_obs 1.059 _refine_ls_restrained_S_all 1.208 _refine_ls_restrained_S_obs 1.059 _refine_ls_shift/esd_max 0.000 _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 Cl1 Cl 0.06352(13) 0.78241(5) 0.64617(8) 0.0782(4) Uani 1 d . . Cl2 Cl -0.0972(2) 0.78622(7) 0.39279(9) 0.0934(5) Uani 1 d . . P1 P -0.28845(13) 0.91732(5) 0.74718(8) 0.0635(4) Uani 1 d . . C1 C -0.3325(5) 0.8326(2) 0.5509(3) 0.0651(9) Uani 1 d . . C2 C -0.3538(5) 0.8252(2) 0.6793(3) 0.0668(9) Uani 1 d . . H2A H -0.2641(5) 0.7863(2) 0.7217(3) 0.075(5) Uiso 1 calc R . H2B H -0.4906(5) 0.8118(2) 0.6809(3) 0.075(5) Uiso 1 calc R . C3 C -0.1244(5) 0.9454(2) 0.6495(3) 0.0690(10) Uani 1 d . . H3A H -0.1378(5) 0.9993(2) 0.6312(3) 0.075(5) Uiso 1 calc R . H3B H 0.0149(5) 0.9344(2) 0.6873(3) 0.075(5) Uiso 1 calc R . C4 C -0.1937(5) 0.8990(2) 0.5387(3) 0.0671(9) Uani 1 d . . H4 H -0.2279(5) 0.9272(2) 0.4629(3) 0.071(9) Uiso 1 calc R . C5 C -0.1249(5) 0.8198(2) 0.5317(3) 0.0666(9) Uani 1 d . . C6 C -0.5189(5) 0.8161(2) 0.4539(3) 0.0831(11) Uani 1 d . . H6A H -0.6359(5) 0.8277(2) 0.4830(3) 0.162(12) Uiso 1 calc R . H6B H -0.5209(5) 0.7632(2) 0.4324(3) 0.162(12) Uiso 1 calc R . H6C H -0.5184(5) 0.8467(2) 0.3846(3) 0.162(12) Uiso 1 calc R . C7 C -0.1485(5) 0.9053(2) 0.8991(3) 0.0620(9) Uani 1 d . . C8 C 0.0545(5) 0.8899(2) 0.9292(3) 0.0781(10) Uani 1 d . . H8 H 0.1249(5) 0.8870(2) 0.8691(3) 0.096(6) Uiso 1 calc R . C9 C 0.1533(6) 0.8789(2) 1.0454(3) 0.0822(11) Uani 1 d . . H9 H 0.2902(6) 0.8684(2) 1.0645(3) 0.096(6) Uiso 1 calc R . C10 C 0.0508(6) 0.8834(2) 1.1344(3) 0.0810(11) Uani 1 d . . H10 H 0.1182(6) 0.8761(2) 1.2140(3) 0.096(6) Uiso 1 calc R . C11 C -0.1483(7) 0.8986(2) 1.1066(4) 0.0911(12) Uani 1 d . . H11 H -0.2178(7) 0.9012(2) 1.1671(4) 0.096(6) Uiso 1 calc R . C12 C -0.2479(6) 0.9101(2) 0.9894(4) 0.0816(11) Uani 1 d . . H12 H -0.3844(6) 0.9214(2) 0.9711(4) 0.096(6) Uiso 1 calc R . B1 B -0.5241(7) 0.9776(3) 0.7240(5) 0.0846(13) Uani 1 d . . H1C H -0.5868(7) 0.9803(3) 0.6398(5) 0.116(8) Uiso 1 calc R . H1D H -0.4893(7) 1.0280(3) 0.7543(5) 0.116(8) Uiso 1 calc R . H1E H -0.6155(7) 0.9552(3) 0.7660(5) 0.116(8) Uiso 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 Cl1 0.0614(6) 0.0930(7) 0.0732(7) 0.0041(4) 0.0017(4) 0.0090(5) Cl2 0.0862(7) 0.1307(10) 0.0644(7) -0.0137(5) 0.0198(5) -0.0045(6) P1 0.0566(6) 0.0685(7) 0.0641(7) 0.0030(4) 0.0116(4) 0.0015(4) C1 0.054(2) 0.076(2) 0.061(2) 0.004(2) 0.0059(14) -0.002(2) C2 0.057(2) 0.077(2) 0.066(2) 0.003(2) 0.014(2) -0.006(2) C3 0.065(2) 0.070(2) 0.070(2) 0.008(2) 0.012(2) -0.007(2) C4 0.062(2) 0.080(2) 0.057(2) 0.012(2) 0.0079(15) 0.000(2) C5 0.058(2) 0.085(2) 0.053(2) 0.000(2) 0.0070(15) 0.005(2) C6 0.066(2) 0.100(3) 0.075(2) 0.002(2) -0.002(2) -0.004(2) C7 0.062(2) 0.060(2) 0.064(2) -0.0015(14) 0.014(2) -0.003(2) C8 0.068(2) 0.101(3) 0.064(2) 0.001(2) 0.014(2) 0.002(2) C9 0.072(2) 0.100(3) 0.070(3) -0.001(2) 0.006(2) 0.001(2) C10 0.096(3) 0.074(2) 0.065(3) 0.000(2) 0.003(2) -0.004(2) C11 0.107(3) 0.106(3) 0.065(3) 0.006(2) 0.030(2) 0.011(3) C12 0.078(2) 0.096(3) 0.074(3) 0.006(2) 0.023(2) 0.009(2) B1 0.067(3) 0.086(3) 0.097(3) 0.004(2) 0.012(2) 0.010(3) _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 Cl1 C5 1.739(3) . ? Cl2 C5 1.750(3) . ? P1 C7 1.792(3) . ? P1 C2 1.806(4) . ? P1 C3 1.830(3) . ? P1 B1 1.897(5) . ? C1 C5 1.506(5) . ? C1 C6 1.511(5) . ? C1 C2 1.519(5) . ? C1 C4 1.531(5) . ? C3 C4 1.490(5) . ? C4 C5 1.476(5) . ? C7 C12 1.369(5) . ? C7 C8 1.379(5) . ? C8 C9 1.358(5) . ? C9 C10 1.369(5) . ? C10 C11 1.353(5) . ? C11 C12 1.371(6) . ? 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 C7 P1 C2 109.6(2) . . ? C7 P1 C3 111.2(2) . . ? C2 P1 C3 96.0(2) . . ? C7 P1 B1 116.5(2) . . ? C2 P1 B1 108.9(2) . . ? C3 P1 B1 112.9(2) . . ? C5 C1 C6 121.9(3) . . ? C5 C1 C2 116.0(3) . . ? C6 C1 C2 116.0(3) . . ? C5 C1 C4 58.2(2) . . ? C6 C1 C4 121.0(3) . . ? C2 C1 C4 110.9(3) . . ? C1 C2 P1 105.6(2) . . ? C4 C3 P1 104.8(2) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 C1 60.1(2) . . ? C3 C4 C1 114.8(3) . . ? C4 C5 C1 61.8(2) . . ? C4 C5 Cl1 120.3(2) . . ? C1 C5 Cl1 120.4(2) . . ? C4 C5 Cl2 118.1(2) . . ? C1 C5 Cl2 119.4(2) . . ? Cl1 C5 Cl2 109.8(2) . . ? C12 C7 C8 118.3(3) . . ? C12 C7 P1 118.7(3) . . ? C8 C7 P1 123.0(3) . . ? C9 C8 C7 121.0(4) . . ? C8 C9 C10 119.8(4) . . ? C11 C10 C9 120.1(4) . . ? C10 C11 C12 120.1(4) . . ? C7 C12 C11 120.7(4) . . ? 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 C5 C1 C2 P1 85.5(3) . . . . ? C6 C1 C2 P1 -121.5(3) . . . . ? C4 C1 C2 P1 21.7(3) . . . . ? C7 P1 C2 C1 -141.5(2) . . . . ? C3 P1 C2 C1 -26.6(2) . . . . ? B1 P1 C2 C1 90.1(3) . . . . ? C7 P1 C3 C4 137.2(2) . . . . ? C2 P1 C3 C4 23.6(3) . . . . ? B1 P1 C3 C4 -89.8(3) . . . . ? P1 C3 C4 C5 -82.8(3) . . . . ? P1 C3 C4 C1 -14.0(3) . . . . ? C5 C1 C4 C5 0.0 . . . . ? C6 C1 C4 C5 -110.6(4) . . . . ? C2 C1 C4 C5 108.3(3) . . . . ? C5 C1 C4 C3 -113.3(3) . . . . ? C6 C1 C4 C3 136.1(3) . . . . ? C2 C1 C4 C3 -5.0(4) . . . . ? C3 C4 C5 C1 102.5(3) . . . . ? C1 C4 C5 C1 0.0 . . . . ? C3 C4 C5 Cl1 -8.1(4) . . . . ? C1 C4 C5 Cl1 -110.5(3) . . . . ? C3 C4 C5 Cl2 -147.3(3) . . . . ? C1 C4 C5 Cl2 110.2(3) . . . . ? C6 C1 C5 C4 109.2(4) . . . . ? C2 C1 C5 C4 -99.5(3) . . . . ? C4 C1 C5 C4 0.0 . . . . ? C6 C1 C5 Cl1 -140.4(3) . . . . ? C2 C1 C5 Cl1 11.0(4) . . . . ? C4 C1 C5 Cl1 110.5(3) . . . . ? C6 C1 C5 Cl2 1.0(5) . . . . ? C2 C1 C5 Cl2 152.3(3) . . . . ? C4 C1 C5 Cl2 -108.2(3) . . . . ? C2 P1 C7 C12 -97.2(3) . . . . ? C3 P1 C7 C12 158.0(3) . . . . ? B1 P1 C7 C12 26.9(4) . . . . ? C2 P1 C7 C8 81.5(3) . . . . ? C3 P1 C7 C8 -23.3(4) . . . . ? B1 P1 C7 C8 -154.4(3) . . . . ? C12 C7 C8 C9 0.7(6) . . . . ? P1 C7 C8 C9 -178.0(3) . . . . ? C7 C8 C9 C10 -0.2(6) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C9 C10 C11 C12 -0.6(7) . . . . ? C8 C7 C12 C11 -1.1(6) . . . . ? P1 C7 C12 C11 177.6(3) . . . . ? C10 C11 C12 C7 1.1(6) . . . . ? _refine_diff_density_max 0.389 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.083 data_fm30 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.361(6) _cell_length_b 11.236(6) _cell_length_c 6.912(2) _cell_angle_alpha 104.73(3) _cell_angle_beta 107.85(2) _cell_angle_gamma 65.89(2) _cell_volume 624.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description unknown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method ? _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device unknown _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 4259 _diffrn_reflns_av_R_equivalents 0.1640 _diffrn_reflns_av_sigmaI/netI 0.1209 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 22.67 _reflns_number_total 1400 _reflns_number_observed 1266 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan: PROCESS (MSC)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'teXsan: FINISH (MSC)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1443P)^2^+0.2110P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.6147(949) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1394 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_obs 0.0757 _refine_ls_wR_factor_all 0.2613 _refine_ls_wR_factor_obs 0.1990 _refine_ls_goodness_of_fit_all 1.126 _refine_ls_goodness_of_fit_obs 1.037 _refine_ls_restrained_S_all 1.290 _refine_ls_restrained_S_obs 1.037 _refine_ls_shift/esd_max 0.000 _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 P1 P 0.20041(11) 0.19146(9) 0.37626(14) 0.0573(7) Uani 1 d . . C1 C 0.1403(5) 0.3109(4) 0.2065(6) 0.0599(11) Uani 1 d . . H1A H 0.0942(5) 0.2779(4) 0.0676(6) 0.079(6) Uiso 1 calc R . H1B H 0.0612(5) 0.3932(4) 0.2530(6) 0.079(6) Uiso 1 calc R . C2 C 0.2946(5) 0.3318(4) 0.2138(7) 0.0641(12) Uani 1 d . . H2 H 0.3514(5) 0.2587(4) 0.1200(7) 0.055(7) Uiso 1 calc R . C3 C 0.4028(5) 0.3173(4) 0.4324(6) 0.0649(12) Uani 1 d . . H3 H 0.5120(5) 0.3045(4) 0.4285(6) 0.055(7) Uiso 1 calc R . C4 C 0.4059(5) 0.1918(4) 0.4827(7) 0.0684(12) Uani 1 d . . H4A H 0.4359(5) 0.1922(4) 0.6302(7) 0.079(6) Uiso 1 calc R . H4B H 0.4822(5) 0.1146(4) 0.4202(7) 0.079(6) Uiso 1 calc R . C5 C 0.2581(6) 0.4568(5) 0.1358(7) 0.0825(14) Uani 1 d . . H5A H 0.3569(6) 0.4664(5) 0.1427(7) 0.118(8) Uiso 1 calc R . H5B H 0.1966(6) 0.5307(5) 0.2191(7) 0.118(8) Uiso 1 calc R . H5C H 0.1974(6) 0.4531(5) -0.0041(7) 0.118(8) Uiso 1 calc R . C6 C 0.3466(6) 0.4357(4) 0.5913(7) 0.0780(14) Uani 1 d . . H6A H 0.3464(6) 0.5125(4) 0.5540(7) 0.118(8) Uiso 1 calc R . H6B H 0.4180(6) 0.4205(4) 0.7234(7) 0.118(8) Uiso 1 calc R . H6C H 0.2398(6) 0.4493(4) 0.5972(7) 0.118(8) Uiso 1 calc R . C7 C 0.2159(4) 0.0336(4) 0.2219(6) 0.0554(11) Uani 1 d . . C8 C 0.1713(5) -0.0519(4) 0.2806(7) 0.0665(12) Uani 1 d . . H8 H 0.1293(5) -0.0260(4) 0.3968(7) 0.097(7) Uiso 1 calc R . C9 C 0.1880(5) -0.1751(4) 0.1694(8) 0.0792(14) Uani 1 d . . H9 H 0.1601(5) -0.2330(4) 0.2126(8) 0.097(7) Uiso 1 calc R . C10 C 0.2448(5) -0.2123(5) -0.0026(9) 0.0840(15) Uani 1 d . . H10 H 0.2550(5) -0.2955(5) -0.0783(9) 0.097(7) Uiso 1 calc R . C11 C 0.2870(6) -0.1288(5) -0.0655(8) 0.0813(14) Uani 1 d . . H11 H 0.3250(6) -0.1549(5) -0.1849(8) 0.097(7) Uiso 1 calc R . C12 C 0.2740(5) -0.0060(4) 0.0455(7) 0.0707(13) Uani 1 d . . H12 H 0.3042(5) 0.0503(4) 0.0020(7) 0.097(7) Uiso 1 calc R . B1 B 0.0764(8) 0.2383(6) 0.5720(9) 0.083(2) Uani 1 d . . H1C H 0.0729(8) 0.3232(6) 0.6489(9) 0.110(10) Uiso 1 calc R . H1D H 0.1240(8) 0.1738(6) 0.6637(9) 0.110(10) Uiso 1 calc R . H1E H -0.0309(8) 0.2417(6) 0.5029(9) 0.110(10) Uiso 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 P1 0.0606(10) 0.0528(10) 0.0594(10) 0.0150(6) 0.0153(6) -0.0164(6) C1 0.062(2) 0.055(2) 0.061(2) 0.017(2) 0.013(2) -0.014(2) C2 0.069(3) 0.054(2) 0.075(3) 0.013(2) 0.025(2) -0.020(2) C3 0.058(2) 0.066(2) 0.072(3) 0.018(2) 0.008(2) -0.024(2) C4 0.064(3) 0.062(2) 0.073(3) 0.020(2) 0.004(2) -0.019(2) C5 0.103(3) 0.077(3) 0.084(3) 0.023(3) 0.022(3) -0.041(2) C6 0.094(3) 0.069(3) 0.070(3) -0.001(2) 0.020(2) -0.034(2) C7 0.055(2) 0.051(2) 0.056(2) 0.007(2) 0.013(2) -0.015(2) C8 0.065(3) 0.064(3) 0.076(3) 0.014(2) 0.020(2) -0.024(2) C9 0.076(3) 0.062(3) 0.107(4) 0.012(3) 0.021(3) -0.032(2) C10 0.072(3) 0.058(3) 0.112(4) 0.007(3) 0.017(3) -0.020(2) C11 0.082(3) 0.074(3) 0.081(3) 0.003(3) 0.028(2) -0.019(2) C12 0.081(3) 0.057(3) 0.078(3) 0.006(2) 0.030(2) -0.021(2) B1 0.102(4) 0.077(3) 0.079(4) 0.006(3) 0.039(3) -0.032(3) _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 P1 C7 1.796(4) . ? P1 C1 1.810(4) . ? P1 C4 1.838(4) . ? P1 B1 1.886(5) . ? C1 C2 1.539(6) . ? C2 C5 1.503(6) . ? C2 C3 1.545(6) . ? C3 C6 1.514(6) . ? C3 C4 1.523(6) . ? C7 C8 1.376(6) . ? C7 C12 1.383(6) . ? C8 C9 1.374(6) . ? C9 C10 1.351(7) . ? C10 C11 1.357(7) . ? C11 C12 1.374(6) . ? 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 C7 P1 C1 108.3(2) . . ? C7 P1 C4 107.2(2) . . ? C1 P1 C4 95.5(2) . . ? C7 P1 B1 113.7(2) . . ? C1 P1 B1 115.6(2) . . ? C4 P1 B1 114.9(3) . . ? C2 C1 P1 105.9(3) . . ? C5 C2 C1 111.9(3) . . ? C5 C2 C3 116.1(3) . . ? C1 C2 C3 107.9(3) . . ? C6 C3 C4 112.1(4) . . ? C6 C3 C2 113.5(3) . . ? C4 C3 C2 105.6(3) . . ? C3 C4 P1 105.5(3) . . ? C8 C7 C12 118.4(4) . . ? C8 C7 P1 119.7(3) . . ? C12 C7 P1 121.9(3) . . ? C9 C8 C7 120.7(4) . . ? C10 C9 C8 120.1(4) . . ? C9 C10 C11 120.3(4) . . ? C10 C11 C12 120.6(4) . . ? C11 C12 C7 119.9(4) . . ? 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 C7 P1 C1 C2 -101.4(3) . . . . ? C4 P1 C1 C2 8.8(3) . . . . ? B1 P1 C1 C2 129.8(3) . . . . ? P1 C1 C2 C5 -162.0(3) . . . . ? P1 C1 C2 C3 -33.2(4) . . . . ? C5 C2 C3 C6 50.7(5) . . . . ? C1 C2 C3 C6 -75.7(4) . . . . ? C5 C2 C3 C4 173.9(3) . . . . ? C1 C2 C3 C4 47.5(4) . . . . ? C6 C3 C4 P1 85.1(4) . . . . ? C2 C3 C4 P1 -39.0(4) . . . . ? C7 P1 C4 C3 128.9(3) . . . . ? C1 P1 C4 C3 17.8(3) . . . . ? B1 P1 C4 C3 -103.7(3) . . . . ? C1 P1 C7 C8 -143.8(3) . . . . ? C4 P1 C7 C8 114.2(3) . . . . ? B1 P1 C7 C8 -13.9(4) . . . . ? C1 P1 C7 C12 37.1(4) . . . . ? C4 P1 C7 C12 -64.9(4) . . . . ? B1 P1 C7 C12 167.0(4) . . . . ? C12 C7 C8 C9 1.7(6) . . . . ? P1 C7 C8 C9 -177.4(3) . . . . ? C7 C8 C9 C10 -1.7(7) . . . . ? C8 C9 C10 C11 0.6(7) . . . . ? C9 C10 C11 C12 0.6(7) . . . . ? C10 C11 C12 C7 -0.7(7) . . . . ? C8 C7 C12 C11 -0.5(6) . . . . ? P1 C7 C12 C11 178.6(3) . . . . ? _refine_diff_density_max 0.365 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.113