# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers # This journal is © The Partner Organisations 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H10 N, Cd Cl3, 2(H0.50), (H0.50)' _chemical_formula_sum 'C5 H12 Cd Cl3 N' _chemical_formula_weight 304.92 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C m c m' _symmetry_space_group_name_Hall '-C 2c 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 7.537(6) _cell_length_b 19.877(16) _cell_length_c 6.662(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 998.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 333(2) _cell_measurement_reflns_used 12903 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.029 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.363 _exptl_absorpt_correction_T_max 0.441 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 333(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 'Rigaku SCXmini diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1968 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.46 _reflns_number_total 666 _reflns_number_gt 565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'PRPKAPPA (Ferguson, 1999)' _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^)+(0.0351P)^2^+0.3135P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 666 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0599 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Cd1 Cd 0.0000 0.0000 0.0000 0.04655(17) Uani 1 4 d S . . Cl2 Cl 0.0000 -0.10125(6) -0.2500 0.0621(4) Uani 1 4 d S . . Cl3 Cl -0.24049(11) 0.04971(5) -0.2500 0.0562(2) Uani 1 2 d S . . N1 N -0.018(5) 0.4154(4) -0.1714(12) 0.084(6) Uani 0.25 1 d P . . H1B H 0.0295 0.4362 -0.0641 0.126 Uiso 0.25 1 d PR . . H1C H 0.0000 0.4382 -0.2835 0.126 Uiso 0.50 2 d SPR . . H1D H -0.1368 0.4138 -0.1581 0.126 Uiso 0.25 1 d PR . . C1 C 0.0521(11) 0.3464(5) -0.1859(16) 0.054(3) Uani 0.25 1 d P . . H1A H 0.1732 0.3516 -0.2277 0.065 Uiso 0.25 1 d PR . . C2 C 0.051(2) 0.2971(9) -0.069(3) 0.067(5) Uani 0.25 1 d P . . H2A H 0.0000 0.3102 0.0547 0.081 Uiso 0.50 2 d SPR . . H2B H 0.1705 0.2837 -0.0407 0.081 Uiso 0.25 1 d PR . . C3 C -0.046(3) 0.2358(12) -0.182(4) 0.102(10) Uani 0.25 1 d P . . H3A H -0.1615 0.2306 -0.1235 0.122 Uiso 0.25 1 d PR . . H3B H 0.0000 0.1942 -0.1714 0.122 Uiso 0.50 2 d SPR . . C4 C -0.064(8) 0.2569(14) -0.367(7) 0.26(4) Uani 0.25 1 d P . . H4A H -0.1719 0.2395 -0.4223 0.307 Uiso 0.25 1 d PR . . H4B H 0.0319 0.2359 -0.4388 0.307 Uiso 0.25 1 d PR . . C5 C -0.033(9) 0.3223(10) -0.400(3) 0.19(2) Uani 0.25 1 d P . . H5A H 0.0239 0.3315 -0.5202 0.224 Uiso 0.25 1 d PR . . H5B H -0.1492 0.3418 -0.4079 0.224 Uiso 0.25 1 d PR . . 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 Cd1 0.0490(3) 0.0626(3) 0.0281(2) -0.00249(12) 0.000 0.000 Cl2 0.0999(11) 0.0438(6) 0.0427(6) 0.000 0.000 0.000 Cl3 0.0523(5) 0.0722(5) 0.0440(4) 0.000 0.000 0.0169(4) N1 0.111(15) 0.055(4) 0.086(6) -0.016(3) 0.049(13) -0.011(8) C1 0.042(5) 0.046(5) 0.073(10) -0.011(4) 0.008(4) -0.008(3) C2 0.080(13) 0.059(11) 0.063(8) 0.020(9) -0.005(7) -0.001(6) C3 0.088(19) 0.053(8) 0.17(3) 0.040(12) 0.008(13) 0.004(6) C4 0.32(6) 0.10(2) 0.35(6) -0.08(3) -0.27(5) 0.03(3) C5 0.43(6) 0.065(12) 0.070(12) -0.039(10) -0.11(3) 0.09(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 Cd1 Cl2 2.6124(17) . ? Cd1 Cl2 2.6124(17) 9 ? Cd1 Cl3 2.6525(14) 3_554 ? Cd1 Cl3 2.6525(14) 9 ? Cd1 Cl3 2.6525(14) 11_556 ? Cd1 Cl3 2.6525(14) . ? Cd1 Cd1 3.331(3) 2_554 ? Cd1 Cd1 3.331(3) 2 ? Cl2 Cd1 2.6123(17) 2_554 ? Cl3 Cd1 2.6525(14) 2_554 ? N1 N1 0.27(8) 12 ? N1 N1 1.047(16) 10 ? N1 N1 1.08(2) 3_554 ? N1 C1 1.398(14) 12 ? N1 C1 1.473(19) . ? N1 C1 1.688(14) 3_554 ? N1 C1 1.750(17) 10 ? N1 C5 1.913(19) 10 ? N1 C5 1.95(3) 3_554 ? C1 C5 0.76(2) 3_554 ? C1 C1 0.785(17) 12 ? C1 C1 0.85(2) 10 ? C1 C5 0.98(4) 10 ? C1 C1 1.160(19) 3_554 ? C1 C2 1.252(17) . ? C1 N1 1.398(14) 12 ? C1 C2 1.472(17) 12 ? C1 C5 1.51(2) 12 ? C1 C5 1.63(3) . ? C1 N1 1.688(14) 3_554 ? C2 C5 0.56(2) 3_554 ? C2 C2 0.76(3) 12 ? C2 C5 0.83(5) 10 ? C2 C4 0.91(4) 3_554 ? C2 C4 1.25(6) 10 ? C2 C3 1.43(3) 12 ? C2 C1 1.472(17) 12 ? C2 C3 1.60(3) . ? C2 C1 1.90(2) 10 ? C3 C4 0.55(6) 10 ? C3 C3 0.69(4) 12 ? C3 C3 0.91(6) 10 ? C3 C4 0.98(4) 3_554 ? C3 C3 1.14(5) 3_554 ? C3 C4 1.31(3) . ? C3 C2 1.43(3) 12 ? C3 C4 1.54(3) 12 ? C3 C5 1.80(4) 10 ? C3 C5 1.90(4) 3_554 ? C4 C3 0.55(6) 10 ? C4 C2 0.91(4) 3_554 ? C4 C4 0.96(11) 12 ? C4 C3 0.98(4) 3_554 ? C4 C2 1.25(6) 10 ? C4 C5 1.34(4) . ? C4 C5 1.51(5) 12 ? C4 C3 1.54(3) 12 ? C4 C4 1.56(10) 10 ? C4 C1 1.82(3) 3_554 ? C4 C4 1.83(7) 3_554 ? C5 C5 0.50(13) 12 ? C5 C2 0.56(2) 3_554 ? C5 C1 0.76(2) 3_554 ? C5 C2 0.83(5) 10 ? C5 C1 0.98(4) 10 ? C5 C4 1.51(5) 12 ? C5 C1 1.51(2) 12 ? C5 C3 1.80(4) 10 ? C5 C3 1.90(4) 3_554 ? C5 N1 1.913(19) 10 ? 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 Cl2 Cd1 Cl2 180.00(3) . 9 ? Cl2 Cd1 Cl3 83.49(5) . 3_554 ? Cl2 Cd1 Cl3 96.51(5) 9 3_554 ? Cl2 Cd1 Cl3 96.51(5) . 9 ? Cl2 Cd1 Cl3 83.49(5) 9 9 ? Cl3 Cd1 Cl3 93.79(6) 3_554 9 ? Cl2 Cd1 Cl3 96.51(5) . 11_556 ? Cl2 Cd1 Cl3 83.49(5) 9 11_556 ? Cl3 Cd1 Cl3 180.0 3_554 11_556 ? Cl3 Cd1 Cl3 86.21(6) 9 11_556 ? Cl2 Cd1 Cl3 83.49(5) . . ? Cl2 Cd1 Cl3 96.51(5) 9 . ? Cl3 Cd1 Cl3 86.21(6) 3_554 . ? Cl3 Cd1 Cl3 180.0 9 . ? Cl3 Cd1 Cl3 93.79(6) 11_556 . ? Cl2 Cd1 Cd1 50.39(4) . 2_554 ? Cl2 Cd1 Cd1 129.61(3) 9 2_554 ? Cl3 Cd1 Cd1 51.11(3) 3_554 2_554 ? Cl3 Cd1 Cd1 128.90(3) 9 2_554 ? Cl3 Cd1 Cd1 128.90(3) 11_556 2_554 ? Cl3 Cd1 Cd1 51.11(3) . 2_554 ? Cl2 Cd1 Cd1 129.61(3) . 2 ? Cl2 Cd1 Cd1 50.39(4) 9 2 ? Cl3 Cd1 Cd1 128.90(3) 3_554 2 ? Cl3 Cd1 Cd1 51.10(3) 9 2 ? Cl3 Cd1 Cd1 51.10(3) 11_556 2 ? Cl3 Cd1 Cd1 128.90(3) . 2 ? Cd1 Cd1 Cd1 180.0 2_554 2 ? Cd1 Cl2 Cd1 79.22(7) 2_554 . ? Cd1 Cl3 Cd1 77.79(6) . 2_554 ? N1 N1 N1 90.000(9) 12 10 ? N1 N1 N1 75(4) 12 3_554 ? N1 N1 N1 15(4) 10 3_554 ? N1 N1 C1 100.6(17) 12 12 ? N1 N1 C1 86.0(6) 10 12 ? N1 N1 C1 88.8(8) 3_554 12 ? N1 N1 C1 69.0(15) 12 . ? N1 N1 C1 86.2(6) 10 . ? N1 N1 C1 81.2(17) 3_554 . ? C1 N1 C1 31.6(7) 12 . ? N1 N1 C1 98.7(14) 12 3_554 ? N1 N1 C1 55.7(4) 10 3_554 ? N1 N1 C1 59.5(11) 3_554 3_554 ? C1 N1 C1 30.3(8) 12 3_554 ? C1 N1 C1 42.4(7) . 3_554 ? N1 N1 C1 72.4(13) 12 10 ? N1 N1 C1 57.1(5) 10 10 ? N1 N1 C1 53.0(10) 3_554 10 ? C1 N1 C1 41.4(7) 12 10 ? C1 N1 C1 29.2(8) . 10 ? C1 N1 C1 26.3(6) 3_554 10 ? N1 N1 C5 93(2) 12 10 ? N1 N1 C5 104.3(7) 10 10 ? N1 N1 C5 104.7(7) 3_554 10 ? C1 N1 C5 19.6(13) 12 10 ? C1 N1 C5 30.3(15) . 10 ? C1 N1 C5 49.1(9) 3_554 10 ? C1 N1 C5 52.7(9) 10 10 ? N1 N1 C5 79(2) 12 3_554 ? N1 N1 C5 104.0(7) 10 3_554 ? N1 N1 C5 100.7(17) 3_554 3_554 ? C1 N1 C5 28.5(15) 12 3_554 ? C1 N1 C5 20.1(14) . 3_554 ? C1 N1 C5 52.8(8) 3_554 3_554 ? C1 N1 C5 47.8(10) 10 3_554 ? C5 N1 C5 15(4) 10 3_554 ? C5 C1 C1 79(5) 3_554 12 ? C5 C1 C1 138.7(18) 3_554 10 ? C1 C1 C1 90.000(4) 12 10 ? C5 C1 C5 30(8) 3_554 10 ? C1 C1 C5 49(3) 12 10 ? C1 C1 C5 125(3) 10 10 ? C5 C1 C1 115(4) 3_554 3_554 ? C1 C1 C1 47.4(10) 12 3_554 ? C1 C1 C1 42.6(10) 10 3_554 ? C5 C1 C1 89(3) 10 3_554 ? C5 C1 C2 15(4) 3_554 . ? C1 C1 C2 89.5(9) 12 . ? C1 C1 C2 128.5(11) 10 . ? C5 C1 C2 42(3) 10 . ? C1 C1 C2 116.9(11) 3_554 . ? C5 C1 N1 122(3) 3_554 12 ? C1 C1 N1 79.4(17) 12 12 ? C1 C1 N1 94.0(6) 10 12 ? C5 C1 N1 109(2) 10 12 ? C1 C1 N1 85.8(11) 3_554 12 ? C2 C1 N1 136.3(14) . 12 ? C5 C1 C2 23(4) 3_554 12 ? C1 C1 C2 58.3(6) 12 12 ? C1 C1 C2 122.0(9) 10 12 ? C5 C1 C2 12.9(19) 10 12 ? C1 C1 C2 91.9(10) 3_554 12 ? C2 C1 C2 31.3(13) . 12 ? N1 C1 C2 121.3(16) 12 12 ? C5 C1 N1 118(4) 3_554 . ? C1 C1 N1 69.0(15) 12 . ? C1 C1 N1 93.8(6) 10 . ? C5 C1 N1 100(2) 10 . ? C1 C1 N1 78.8(12) 3_554 . ? C2 C1 N1 133.2(13) . . ? N1 C1 N1 10(3) 12 . ? C2 C1 N1 113.3(14) 12 . ? C5 C1 C5 119(3) 3_554 12 ? C1 C1 C5 85(2) 12 12 ? C1 C1 C5 19.4(8) 10 12 ? C5 C1 C5 109.3(19) 10 12 ? C1 C1 C5 41(2) 3_554 12 ? C2 C1 C5 109.8(12) . 12 ? N1 C1 C5 111.0(13) 12 12 ? C2 C1 C5 103.8(15) 12 12 ? N1 C1 C5 108.9(17) . 12 ? C5 C1 C5 113(2) 3_554 . ? C1 C1 C5 67(2) 12 . ? C1 C1 C5 29.3(19) 10 . ? C5 C1 C5 96(4) 10 . ? C1 C1 C5 24.8(17) 3_554 . ? C2 C1 C5 108.0(13) . . ? N1 C1 C5 106.0(11) 12 . ? C2 C1 C5 93.4(17) 12 . ? N1 C1 C5 100.9(13) . . ? C5 C1 C5 18(5) 12 . ? C5 C1 N1 155(5) 3_554 3_554 ? C1 C1 N1 81.3(14) 12 3_554 ? C1 C1 N1 55.7(4) 10 3_554 ? C5 C1 N1 129(3) 10 3_554 ? C1 C1 N1 58.8(11) 3_554 3_554 ? C2 C1 N1 170.1(17) . 3_554 ? N1 C1 N1 38.2(6) 12 3_554 ? C2 C1 N1 139.4(16) 12 3_554 ? N1 C1 N1 39.3(9) . 3_554 ? C5 C1 N1 73.3(10) 12 3_554 ? C5 C1 N1 71.8(9) . 3_554 ? C5 C2 C2 76(7) 3_554 12 ? C5 C2 C5 35(10) 3_554 10 ? C2 C2 C5 41(3) 12 10 ? C5 C2 C4 129(5) 3_554 3_554 ? C2 C2 C4 96(4) 12 3_554 ? C5 C2 C4 119(4) 10 3_554 ? C5 C2 C4 106(6) 3_554 10 ? C2 C2 C4 46.5(18) 12 10 ? C5 C2 C4 77(4) 10 10 ? C4 C2 C4 50(5) 3_554 10 ? C5 C2 C1 21(6) 3_554 . ? C2 C2 C1 90.5(9) 12 . ? C5 C2 C1 52(3) 10 . ? C4 C2 C1 113(3) 3_554 . ? C4 C2 C1 107(3) 10 . ? C5 C2 C3 124(4) 3_554 12 ? C2 C2 C3 88.5(11) 12 12 ? C5 C2 C3 111(3) 10 12 ? C4 C2 C3 8(3) 3_554 12 ? C4 C2 C3 42.2(14) 10 12 ? C1 C2 C3 109.9(18) . 12 ? C5 C2 C1 23(5) 3_554 12 ? C2 C2 C1 58.3(6) 12 12 ? C5 C2 C1 21(2) 10 12 ? C4 C2 C1 113(3) 3_554 12 ? C4 C2 C1 83(2) 10 12 ? C1 C2 C1 32.2(8) . 12 ? C3 C2 C1 106.0(17) 12 12 ? C5 C2 C3 113(5) 3_554 . ? C2 C2 C3 63.1(9) 12 . ? C5 C2 C3 90(3) 10 . ? C4 C2 C3 33(3) 3_554 . ? C4 C2 C3 17(2) 10 . ? C1 C2 C3 107.8(16) . . ? C3 C2 C3 25.5(16) 12 . ? C1 C2 C3 91.1(13) 12 . ? C5 C2 C1 39(4) 3_554 10 ? C2 C2 C1 90.3(6) 12 10 ? C5 C2 C1 59(2) 10 10 ? C4 C2 C1 93(3) 3_554 10 ? C4 C2 C1 92(2) 10 10 ? C1 C2 C1 20.6(7) . 10 ? C3 C2 C1 89.3(14) 12 10 ? C1 C2 C1 37.5(7) 12 10 ? C3 C2 C1 89.5(13) . 10 ? C4 C3 C3 104(8) 10 12 ? C4 C3 C3 126(7) 10 10 ? C3 C3 C3 90.000(11) 12 10 ? C4 C3 C4 72(10) 10 3_554 ? C3 C3 C4 33(4) 12 3_554 ? C3 C3 C4 109(4) 10 3_554 ? C4 C3 C3 128(5) 10 3_554 ? C3 C3 C3 53(2) 12 3_554 ? C3 C3 C3 37(2) 10 3_554 ? C4 C3 C3 76(3) 3_554 3_554 ? C4 C3 C4 107(8) 10 . ? C3 C3 C4 96(3) 12 . ? C3 C3 C4 19.6(19) 10 . ? C4 C3 C4 105(4) 3_554 . ? C3 C3 C4 46(2) 3_554 . ? C4 C3 C2 14(6) 10 12 ? C3 C3 C2 91.5(11) 12 12 ? C3 C3 C2 121.7(12) 10 12 ? C4 C3 C2 59(4) 3_554 12 ? C3 C3 C2 115.7(14) 3_554 12 ? C4 C3 C2 103(2) . 12 ? C4 C3 C4 113(6) 10 12 ? C3 C3 C4 58(2) 12 12 ? C3 C3 C4 36.8(17) 10 12 ? C4 C3 C4 72(6) 3_554 12 ? C3 C3 C4 16.1(19) 3_554 12 ? C4 C3 C4 38(5) . 12 ? C2 C3 C4 102(2) 12 12 ? C4 C3 C2 42(8) 10 . ? C3 C3 C2 63.1(9) 12 . ? C3 C3 C2 117.9(11) 10 . ? C4 C3 C2 31(4) 3_554 . ? C3 C3 C2 95.7(17) 3_554 . ? C4 C3 C2 104(3) . . ? C2 C3 C2 28.4(13) 12 . ? C4 C3 C2 85.8(19) 12 . ? C4 C3 C5 27(5) 10 10 ? C3 C3 C5 87(2) 12 10 ? C3 C3 C5 107.4(11) 10 10 ? C4 C3 C5 57(4) 3_554 10 ? C3 C3 C5 101.9(15) 3_554 10 ? C4 C3 C5 89(2) . 10 ? C2 C3 C5 14.9(11) 12 10 ? C4 C3 C5 87(2) 12 10 ? C2 C3 C5 27(2) . 10 ? C4 C3 C5 38(6) 10 3_554 ? C3 C3 C5 72(2) 12 3_554 ? C3 C3 C5 106.6(11) 10 3_554 ? C4 C3 C5 42(4) 3_554 3_554 ? C3 C3 C5 92.2(18) 3_554 3_554 ? C4 C3 C5 91(2) . 3_554 ? C2 C3 C5 24.2(18) 12 3_554 ? C4 C3 C5 79(2) 12 3_554 ? C2 C3 C5 15.7(13) . 3_554 ? C5 C3 C5 15(4) 10 3_554 ? C3 C4 C2 158(9) 10 3_554 ? C3 C4 C4 76(8) 10 12 ? C2 C4 C4 84(4) 3_554 12 ? C3 C4 C3 43(6) 10 3_554 ? C2 C4 C3 116(6) 3_554 3_554 ? C4 C4 C3 33(4) 12 3_554 ? C3 C4 C2 122(9) 10 10 ? C2 C4 C2 37(3) 3_554 10 ? C4 C4 C2 46.5(18) 12 10 ? C3 C4 C2 79(4) 3_554 10 ? C3 C4 C3 34(6) 10 . ? C2 C4 C3 135(3) 3_554 . ? C4 C4 C3 84(3) 12 . ? C3 C4 C3 58(4) 3_554 . ? C2 C4 C3 117(4) 10 . ? C3 C4 C5 143(7) 10 . ? C2 C4 C5 18.8(16) 3_554 . ? C4 C4 C5 80(4) 12 . ? C3 C4 C5 109(5) 3_554 . ? C2 C4 C5 37(3) 10 . ? C3 C4 C5 116(3) . . ? C3 C4 C5 129(8) 10 12 ? C2 C4 C5 29(3) 3_554 12 ? C4 C4 C5 61(3) 12 12 ? C3 C4 C5 91(5) 3_554 12 ? C2 C4 C5 20.9(18) 10 12 ? C3 C4 C5 111(3) . 12 ? C5 C4 C5 19(5) . 12 ? C3 C4 C3 36(4) 10 12 ? C2 C4 C3 124(4) 3_554 12 ? C4 C4 C3 58(2) 12 12 ? C3 C4 C3 34(3) 3_554 12 ? C2 C4 C3 95(3) 10 12 ? C3 C4 C3 26(2) . 12 ? C5 C4 C3 108(3) . 12 ? C5 C4 C3 95(3) 12 12 ? C3 C4 C4 54(7) 10 10 ? C2 C4 C4 118(3) 3_554 10 ? C4 C4 C4 89.998(10) 12 10 ? C3 C4 C4 71(4) 3_554 10 ? C2 C4 C4 110(2) 10 10 ? C3 C4 C4 19.6(18) . 10 ? C5 C4 C4 99(2) . 10 ? C5 C4 C4 98.3(19) 12 10 ? C3 C4 C4 36.9(17) 12 10 ? C3 C4 C1 129(6) 10 3_554 ? C2 C4 C1 39.3(17) 3_554 3_554 ? C4 C4 C1 87.2(18) 12 3_554 ? C3 C4 C1 108(3) 3_554 3_554 ? C2 C4 C1 53.6(11) 10 3_554 ? C3 C4 C1 97(2) . 3_554 ? C5 C4 C1 21.7(15) . 3_554 ? C5 C4 C1 32.7(17) 12 3_554 ? C3 C4 C1 94.9(19) 12 3_554 ? C4 C4 C1 78.9(16) 10 3_554 ? C3 C4 C4 51(5) 10 3_554 ? C2 C4 C4 110(3) 3_554 3_554 ? C4 C4 C4 58(4) 12 3_554 ? C3 C4 C4 44(3) 3_554 3_554 ? C2 C4 C4 86(3) 10 3_554 ? C3 C4 C4 31.1(16) . 3_554 ? C5 C4 C4 93(2) . 3_554 ? C5 C4 C4 83(3) 12 3_554 ? C3 C4 C4 15.9(17) 12 3_554 ? C4 C4 C4 32(4) 10 3_554 ? C1 C4 C4 79.1(13) 3_554 3_554 ? C5 C5 C2 104(7) 12 3_554 ? C5 C5 C1 101(5) 12 3_554 ? C2 C5 C1 143(10) 3_554 3_554 ? C5 C5 C2 41(3) 12 10 ? C2 C5 C2 63(5) 3_554 10 ? C1 C5 C2 136(6) 3_554 10 ? C5 C5 C1 49(3) 12 10 ? C2 C5 C1 144(7) 3_554 10 ? C1 C5 C1 52(2) 3_554 10 ? C2 C5 C1 87(5) 10 10 ? C5 C5 C4 100(4) 12 . ? C2 C5 C4 32(4) 3_554 . ? C1 C5 C4 117(5) 3_554 . ? C2 C5 C4 66(3) 10 . ? C1 C5 C4 119(3) 10 . ? C5 C5 C4 61(3) 12 12 ? C2 C5 C4 53(5) 3_554 12 ? C1 C5 C4 122(3) 3_554 12 ? C2 C5 C4 32(2) 10 12 ? C1 C5 C4 91(4) 10 12 ? C4 C5 C4 39(4) . 12 ? C5 C5 C1 95(2) 12 12 ? C2 C5 C1 128(6) 3_554 12 ? C1 C5 C1 22.0(12) 3_554 12 ? C2 C5 C1 120(4) 10 12 ? C1 C5 C1 50.3(11) 10 12 ? C4 C5 C1 98(3) . 12 ? C4 C5 C1 101(2) 12 12 ? C5 C5 C1 67(2) 12 . ? C2 C5 C1 133(4) 3_554 . ? C1 C5 C1 40(2) 3_554 . ? C2 C5 C1 96(4) 10 . ? C1 C5 C1 25.2(10) 10 . ? C4 C5 C1 102(2) . . ? C4 C5 C1 86(3) 12 . ? C1 C5 C1 28.6(7) 12 . ? C5 C5 C3 93(2) 12 10 ? C2 C5 C3 41(3) 3_554 10 ? C1 C5 C3 112(3) 3_554 10 ? C2 C5 C3 63(2) 10 10 ? C1 C5 C3 109(2) 10 10 ? C4 C5 C3 10(2) . 10 ? C4 C5 C3 32.9(14) 12 10 ? C1 C5 C3 90.8(17) 12 10 ? C1 C5 C3 92.2(14) . 10 ? C5 C5 C3 72(2) 12 3_554 ? C2 C5 C3 51(4) 3_554 3_554 ? C1 C5 C3 115(2) 3_554 3_554 ? C2 C5 C3 45(2) 10 3_554 ? C1 C5 C3 94(3) 10 3_554 ? C4 C5 C3 29(2) . 3_554 ? C4 C5 C3 12.9(19) 12 3_554 ? C1 C5 C3 92.8(14) 12 3_554 ? C1 C5 C3 83.9(15) . 3_554 ? C3 C5 C3 21.3(12) 10 3_554 ? C5 C5 N1 87(2) 12 10 ? C2 C5 N1 167(7) 3_554 10 ? C1 C5 N1 38(2) 3_554 10 ? C2 C5 N1 127(5) 10 10 ? C1 C5 N1 49.2(13) 10 10 ? C4 C5 N1 155(3) . 10 ? C4 C5 N1 140(4) 12 10 ? C1 C5 N1 57.7(6) 12 10 ? C1 C5 N1 58.5(9) . 10 ? C3 C5 N1 148.3(16) 10 10 ? C3 C5 N1 142(2) 3_554 10 ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.500 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 963685' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Cd Cl3, C5 H12 N' _chemical_formula_sum 'C5 H12 Cd Cl3 N' _chemical_formula_weight 304.92 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 7.533(10) _cell_length_b 19.40(2) _cell_length_c 6.753(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.47(2) _cell_angle_gamma 90.00 _cell_volume 985(2) _cell_formula_units_Z 4 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 12903 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.056 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.436 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(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 'Rigaku SCXmini diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5152 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.40 _reflns_number_total 2244 _reflns_number_gt 2022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'PRPKAPPA (Ferguson, 1999)' _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^)+(0.0452P)^2^+0.0000P] 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 0.0264(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 0.36(7) _refine_ls_number_reflns 2244 _refine_ls_number_parameters 93 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 Cd1 Cd 0.00000(19) -0.00100(2) 0.0000(2) 0.02073(16) Uani 1 1 d . . . Cl3 Cl 0.0250(2) -0.10489(7) 0.2513(3) 0.0232(4) Uani 1 1 d . . . Cl2 Cl 0.2353(2) 0.05682(9) 0.2642(2) 0.0240(4) Uani 1 1 d . . . Cl1 Cl -0.2487(2) 0.04324(9) 0.2317(2) 0.0226(4) Uani 1 1 d . . . N1 N -0.5327(7) -0.0868(3) 0.3552(9) 0.0283(13) Uani 1 1 d . . . H1B H -0.5437 -0.0775 0.4830 0.042 Uiso 1 1 calc R . . H1C H -0.6400 -0.0885 0.2925 0.042 Uiso 1 1 calc R . . H1D H -0.4685 -0.0539 0.3017 0.042 Uiso 1 1 calc R . . C1 C -0.4404(9) -0.1559(3) 0.3353(10) 0.0249(14) Uani 1 1 d . . . H1A H -0.3223 -0.1546 0.4046 0.030 Uiso 1 1 calc R . . C5 C -0.5536(10) -0.2142(3) 0.4221(11) 0.0331(17) Uani 1 1 d . . . H5A H -0.4905 -0.2358 0.5353 0.040 Uiso 1 1 calc R . . H5B H -0.6661 -0.1965 0.4627 0.040 Uiso 1 1 calc R . . C2 C -0.4234(11) -0.1737(4) 0.1141(11) 0.0386(19) Uani 1 1 d . . . H2A H -0.4371 -0.1325 0.0332 0.046 Uiso 1 1 calc R . . H2B H -0.3078 -0.1937 0.0945 0.046 Uiso 1 1 calc R . . C3 C -0.5671(12) -0.2240(5) 0.0591(12) 0.045(2) Uani 1 1 d . . . H3A H -0.5347 -0.2532 -0.0495 0.054 Uiso 1 1 calc R . . H3B H -0.6778 -0.2006 0.0214 0.054 Uiso 1 1 calc R . . C4 C -0.5826(14) -0.2658(4) 0.2494(13) 0.054(2) Uani 1 1 d . . . H4A H -0.4933 -0.3018 0.2590 0.064 Uiso 1 1 calc R . . H4B H -0.6992 -0.2869 0.2513 0.064 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 Cd1 0.0202(2) 0.0289(3) 0.0133(2) 0.00062(16) 0.00208(13) -0.00003(17) Cl3 0.0258(9) 0.0207(7) 0.0231(7) 0.0006(8) 0.0016(7) -0.0006(7) Cl2 0.0227(8) 0.0289(9) 0.0207(10) -0.0006(7) 0.0035(7) -0.0061(7) Cl1 0.0197(8) 0.0290(8) 0.0193(9) 0.0008(7) 0.0019(6) 0.0053(7) N1 0.024(3) 0.027(3) 0.034(3) -0.001(3) 0.003(2) -0.001(2) C1 0.019(3) 0.024(3) 0.032(4) -0.002(3) 0.002(3) -0.002(3) C5 0.034(4) 0.020(4) 0.045(5) 0.006(3) 0.005(3) -0.002(3) C2 0.050(5) 0.034(4) 0.034(4) -0.003(4) 0.019(4) -0.002(4) C3 0.052(5) 0.046(5) 0.037(4) -0.010(4) 0.004(4) -0.008(4) C4 0.075(7) 0.030(5) 0.055(5) 0.004(4) -0.005(5) -0.020(4) _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 Cd1 Cl3 2.634(3) . ? Cd1 Cl1 2.655(3) . ? Cd1 Cl1 2.655(3) 2_554 ? Cd1 Cl3 2.667(3) 2_554 ? Cd1 Cl2 2.682(3) 2_554 ? Cd1 Cl2 2.683(3) . ? Cd1 Cd1 3.377(4) 2_554 ? Cd1 Cd1 3.377(4) 2 ? Cl3 Cd1 2.667(3) 2 ? Cl2 Cd1 2.682(3) 2 ? Cl1 Cd1 2.655(3) 2 ? N1 C1 1.519(8) . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? C1 C2 1.546(9) . ? C1 C5 1.553(9) . ? C1 H1A 0.9800 . ? C5 C4 1.542(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C2 C3 1.487(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.530(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? 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 Cl3 Cd1 Cl1 83.87(10) . . ? Cl3 Cd1 Cl1 102.91(9) . 2_554 ? Cl1 Cd1 Cl1 90.47(12) . 2_554 ? Cl3 Cd1 Cl3 171.84(9) . 2_554 ? Cl1 Cd1 Cl3 101.63(9) . 2_554 ? Cl1 Cd1 Cl3 83.21(10) 2_554 2_554 ? Cl3 Cd1 Cl2 92.83(9) . 2_554 ? Cl1 Cd1 Cl2 174.72(7) . 2_554 ? Cl1 Cd1 Cl2 86.25(12) 2_554 2_554 ? Cl3 Cd1 Cl2 82.10(10) 2_554 2_554 ? Cl3 Cd1 Cl2 82.69(10) . . ? Cl1 Cd1 Cl2 86.23(12) . . ? Cl1 Cd1 Cl2 173.17(6) 2_554 . ? Cl3 Cd1 Cl2 91.60(10) 2_554 . ? Cl2 Cd1 Cl2 97.46(12) 2_554 . ? Cl3 Cd1 Cd1 130.44(7) . 2_554 ? Cl1 Cd1 Cd1 128.93(7) . 2_554 ? Cl1 Cd1 Cd1 50.51(7) 2_554 2_554 ? Cl3 Cd1 Cd1 50.00(7) 2_554 2_554 ? Cl2 Cd1 Cd1 51.02(6) 2_554 2_554 ? Cl2 Cd1 Cd1 128.32(7) . 2_554 ? Cl3 Cd1 Cd1 50.87(7) . 2 ? Cl1 Cd1 Cd1 50.52(7) . 2 ? Cl1 Cd1 Cd1 130.02(7) 2_554 2 ? Cl3 Cd1 Cd1 128.70(7) 2_554 2 ? Cl2 Cd1 Cd1 129.67(6) 2_554 2 ? Cl2 Cd1 Cd1 50.97(7) . 2 ? Cd1 Cd1 Cd1 178.69(3) 2_554 2 ? Cd1 Cl3 Cd1 79.13(11) . 2 ? Cd1 Cl2 Cd1 78.01(11) 2 . ? Cd1 Cl1 Cd1 78.97(11) . 2 ? C1 N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1B N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? N1 C1 C2 110.3(5) . . ? N1 C1 C5 110.2(5) . . ? C2 C1 C5 106.4(5) . . ? N1 C1 H1A 110.0 . . ? C2 C1 H1A 110.0 . . ? C5 C1 H1A 110.0 . . ? C4 C5 C1 104.1(6) . . ? C4 C5 H5A 110.9 . . ? C1 C5 H5A 110.9 . . ? C4 C5 H5B 110.9 . . ? C1 C5 H5B 110.9 . . ? H5A C5 H5B 109.0 . . ? C3 C2 C1 106.6(6) . . ? C3 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? C3 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C2 C3 C4 103.3(7) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C3 C4 C5 106.1(6) . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.106 _refine_diff_density_min -0.852 _refine_diff_density_rms 0.364 _database_code_depnum_ccdc_archive 'CCDC 963686'