# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name Yu-Lin Lam*, Ming Wah Wong, Hsing Hua Huang and Eping Liang _publ_contact_author_name 'Yu-Lin Lam' _publ_contact_author_address ; Yu-Lin Lam Department of Chemistry National University of Singapore 3 Science Drive 3 Singapore 117543 ; _publ_contact_author_email 'CHMLAMYL@NUS.EDU.SG' _publ_section_title ; Conformational Analysis of Meso- and (±)- 2,3-Dicyano-2,3-Dicyclopropylbutane and 1,2-Dicyanotetracyclopropylethane ; data_meso-2,3-dicyano-2,3-dicyclopropylbutane _database_code_CSD 164827 _audit_creation_method SHELXL _chemical_name_systematic ; meso-2,3-dicyano-2,3-dicyclopropylbutane ; _chemical_name_common ? _chemical_formula_moiety 'C H N' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H16 N2' _chemical_formula_weight 188.27 _chemical_melting_point 41 C _chemical_compound_source 'see text' 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M P2(1)/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 7.3831(7) _cell_length_b 8.2193(8) _cell_length_c 9.7902(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.292(2) _cell_angle_gamma 90.00 _cell_volume 584.55(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1992 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method ? _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.4404 _exptl_absorpt_correction_T_max 0.9766 _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 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2748 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1023 _reflns_number_observed 793 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0941P)^2^+0.1219P] 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 0.2427(382) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1023 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_obs 0.0599 _refine_ls_wR_factor_all 0.1904 _refine_ls_wR_factor_obs 0.1817 _refine_ls_goodness_of_fit_all 1.133 _refine_ls_goodness_of_fit_obs 1.238 _refine_ls_restrained_S_all 1.133 _refine_ls_restrained_S_obs 1.238 _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 N1 N 0.1157(4) 0.4967(3) 0.3052(2) 0.0892(8) Uani 1 d . . C1 C 0.0357(3) 0.4208(2) 0.0415(2) 0.0533(7) Uani 1 d . . C2 C 0.0785(3) 0.4671(3) 0.1901(2) 0.0637(7) Uani 1 d . . C3 C 0.2145(3) 0.3583(3) -0.0036(3) 0.0721(8) Uani 1 d . . H3A H 0.1883(3) 0.3279(3) -0.0998(3) 0.108 Uiso 1 calc R . H3B H 0.2601(3) 0.2654(3) 0.0515(3) 0.108 Uiso 1 calc R . H3C H 0.3056(3) 0.4428(3) 0.0095(3) 0.108 Uiso 1 calc R . C4 C -0.1100(3) 0.2873(3) 0.0232(2) 0.0630(7) Uani 1 d . . H4 H -0.1518(3) 0.2549(3) -0.0737(2) 0.076 Uiso 1 calc R . C5 C -0.0993(4) 0.1499(3) 0.1234(3) 0.0775(8) Uani 1 d . . H5A H -0.1264(4) 0.0416(3) 0.0860(3) 0.093 Uiso 1 calc R . H5B H -0.0046(4) 0.1546(3) 0.2059(3) 0.093 Uiso 1 calc R . C6 C -0.2528(4) 0.2660(3) 0.1128(3) 0.0845(9) Uani 1 d . . H6A H -0.2521(4) 0.3420(3) 0.1887(3) 0.101 Uiso 1 calc R . H6B H -0.3739(4) 0.2290(3) 0.0687(3) 0.101 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 N1 0.119(2) 0.083(2) 0.0574(13) -0.0025(10) -0.0067(11) -0.0016(13) C1 0.0550(12) 0.0506(12) 0.0530(12) 0.0017(9) 0.0065(8) -0.0004(9) C2 0.073(2) 0.0581(13) 0.0549(13) 0.0058(10) -0.0010(10) -0.0070(11) C3 0.0642(14) 0.0639(15) 0.092(2) 0.0128(12) 0.0249(12) 0.0210(11) C4 0.0721(15) 0.0560(13) 0.0589(12) 0.0018(10) 0.0064(10) -0.0140(10) C5 0.089(2) 0.0560(14) 0.088(2) 0.0124(12) 0.0175(14) -0.0081(12) C6 0.070(2) 0.078(2) 0.109(2) 0.0182(15) 0.0252(14) -0.0098(13) _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 C2 1.138(3) . ? C1 C2 1.482(3) . ? C1 C4 1.525(3) . ? C1 C3 1.552(3) . ? C1 C1 1.576(4) 3_565 ? C4 C5 1.488(3) . ? C4 C6 1.498(3) . ? C5 C6 1.471(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 C4 108.8(2) . . ? C2 C1 C3 108.8(2) . . ? C4 C1 C3 110.3(2) . . ? C2 C1 C1 106.7(2) . 3_565 ? C4 C1 C1 111.7(2) . 3_565 ? C3 C1 C1 110.5(2) . 3_565 ? N1 C2 C1 177.0(2) . . ? C5 C4 C6 59.0(2) . . ? C5 C4 C1 121.0(2) . . ? C6 C4 C1 124.8(2) . . ? C6 C5 C4 60.8(2) . . ? C5 C6 C4 60.2(2) . . ? 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 C4 C1 C2 N1 76.7(49) . . . . ? C3 C1 C2 N1 -43.5(50) . . . . ? C1 C1 C2 N1 -162.7(49) 3_565 . . . ? C2 C1 C4 C5 -42.8(3) . . . . ? C3 C1 C4 C5 76.4(3) . . . . ? C1 C1 C4 C5 -160.4(2) 3_565 . . . ? C2 C1 C4 C6 28.9(3) . . . . ? C3 C1 C4 C6 148.1(2) . . . . ? C1 C1 C4 C6 -88.6(3) 3_565 . . . ? C6 C4 C5 C6 0.0 . . . . ? C1 C4 C5 C6 114.6(3) . . . . ? C4 C5 C6 C4 0.0 . . . . ? C5 C4 C6 C5 0.0 . . . . ? C1 C4 C6 C5 -108.3(2) . . . . ? _refine_diff_density_max 0.418 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.034 #===END data_1,2-dicyanotetracyclopropylethane _database_code_CSD 164828 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-dicyanotetracyclopropylethane ; _chemical_name_common ? _chemical_melting_point 73 C _chemical_formula_moiety 'C H N' _chemical_formula_sum 'C16 H20 N2' _chemical_formula_weight 240.34 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' _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 7.0406(3) _cell_length_b 14.7756(4) _cell_length_c 6.9714(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.1850(10) _cell_angle_gamma 90.00 _cell_volume 703.12(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2462 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'prisms' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.89119 _exptl_absorpt_correction_T_max 0.50915 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4330 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 29.21 _reflns_number_total 1728 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, 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^)+(0.0629P)^2^+0.0394P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.054(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1728 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.005 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 0.31512(19) 0.57148(10) 0.30756(18) 0.0724(4) Uani 1 1 d . . . C1 C 0.47372(15) 0.55220(8) 0.00721(15) 0.0417(3) Uani 1 1 d . . . C2 C 0.65704(18) 0.61191(9) 0.0420(2) 0.0531(3) Uani 1 1 d . . . H2A H 0.720(2) 0.6075(10) -0.063(2) 0.067(4) Uiso 1 1 d . . . C3 C 0.6629(3) 0.70510(11) 0.1316(3) 0.0707(5) Uani 1 1 d . . . H3B H 0.731(3) 0.7518(13) 0.066(3) 0.092(6) Uiso 1 1 d . . . H3A H 0.549(3) 0.7253(12) 0.181(3) 0.086(5) Uiso 1 1 d . . . C4 C 0.7876(2) 0.63069(11) 0.2430(3) 0.0682(4) Uani 1 1 d . . . H4B H 0.747(3) 0.6037(11) 0.355(3) 0.076(5) Uiso 1 1 d . . . H4A H 0.931(3) 0.6297(11) 0.257(3) 0.088(5) Uiso 1 1 d . . . C5 C 0.32732(18) 0.58413(9) -0.18165(18) 0.0505(3) Uani 1 1 d . . . H5A H 0.373(2) 0.5745(10) -0.290(2) 0.065(4) Uiso 1 1 d . . . C6 C 0.2065(2) 0.66778(12) -0.1869(3) 0.0750(5) Uani 1 1 d . . . H6B H 0.216(3) 0.6976(15) -0.058(3) 0.104(7) Uiso 1 1 d . . . H6A H 0.191(3) 0.7054(14) -0.302(3) 0.094(6) Uiso 1 1 d . . . C7 C 0.1101(2) 0.57768(12) -0.2154(3) 0.0679(4) Uani 1 1 d . . . H7B H 0.063(3) 0.5527(12) -0.108(3) 0.084(5) Uiso 1 1 d . . . H7A H 0.036(3) 0.5601(12) -0.352(3) 0.090(5) Uiso 1 1 d . . . C8 C 0.38440(17) 0.56182(9) 0.17753(17) 0.0489(3) Uani 1 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 N1 0.0639(7) 0.1089(11) 0.0492(6) -0.0063(6) 0.0229(6) 0.0111(7) C1 0.0371(5) 0.0560(7) 0.0327(5) 0.0014(4) 0.0102(4) 0.0034(5) C2 0.0456(6) 0.0628(8) 0.0515(7) -0.0014(6) 0.0129(5) -0.0051(6) C3 0.0684(9) 0.0632(9) 0.0739(10) -0.0036(8) 0.0050(8) -0.0067(8) C4 0.0501(8) 0.0747(10) 0.0710(10) -0.0089(8) -0.0019(7) -0.0037(7) C5 0.0475(6) 0.0652(8) 0.0377(6) 0.0082(5) 0.0084(5) 0.0077(6) C6 0.0693(10) 0.0713(10) 0.0742(11) 0.0099(9) -0.0020(8) 0.0187(8) C7 0.0467(7) 0.0853(11) 0.0630(9) 0.0129(8) -0.0028(7) 0.0078(7) C8 0.0410(6) 0.0667(8) 0.0386(6) -0.0013(5) 0.0091(5) 0.0063(5) _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 C8 1.1387(15) . ? C1 C8 1.4804(15) . ? C1 C2 1.5329(17) . ? C1 C5 1.5340(15) . ? C1 C1 1.595(2) 3_665 ? C2 C4 1.501(2) . ? C2 C3 1.508(2) . ? C3 C4 1.499(2) . ? C5 C7 1.4921(19) . ? C5 C6 1.496(2) . ? C6 C7 1.485(3) . ? 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 C8 C1 C2 108.93(10) . . ? C8 C1 C5 109.31(9) . . ? C2 C1 C5 108.75(10) . . ? C8 C1 C1 107.10(11) . 3_665 ? C2 C1 C1 111.54(11) . 3_665 ? C5 C1 C1 111.15(11) . 3_665 ? C4 C2 C3 59.77(10) . . ? C4 C2 C1 123.60(13) . . ? C3 C2 C1 121.85(13) . . ? C4 C3 C2 59.88(10) . . ? C3 C4 C2 60.35(10) . . ? C7 C5 C6 59.62(11) . . ? C7 C5 C1 124.24(12) . . ? C6 C5 C1 122.26(13) . . ? C7 C6 C5 60.07(10) . . ? C6 C7 C5 60.31(10) . . ? N1 C8 C1 178.28(14) . . ? 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 C8 C1 C2 C4 32.75(16) . . . . ? C5 C1 C2 C4 151.81(13) . . . . ? C1 C1 C2 C4 -85.26(16) 3_665 . . . ? C8 C1 C2 C3 -39.85(16) . . . . ? C5 C1 C2 C3 79.21(15) . . . . ? C1 C1 C2 C3 -157.86(13) 3_665 . . . ? C1 C2 C3 C4 113.07(15) . . . . ? C1 C2 C4 C3 -110.25(16) . . . . ? C8 C1 C5 C7 -30.26(17) . . . . ? C2 C1 C5 C7 -149.08(14) . . . . ? C1 C1 C5 C7 87.76(17) 3_665 . . . ? C8 C1 C5 C6 42.65(17) . . . . ? C2 C1 C5 C6 -76.17(16) . . . . ? C1 C1 C5 C6 160.67(14) 3_665 . . . ? C1 C5 C6 C7 -113.66(15) . . . . ? C1 C5 C7 C6 110.45(16) . . . . ? C2 C1 C8 N1 60(4) . . . . ? C5 C1 C8 N1 -59(4) . . . . ? C1 C1 C8 N1 -179(100) 3_665 . . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 29.21 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.216 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.029