# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/212 data_global _publ_contact_author_name 'Martin Lutz' _publ_contact_author_address ; Bijvoet Center for Biomolecular Research Dep. Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; _publ_contact_author_email 'm.lutz@chem.uu.nl' _publ_contact_author_fax '[+31] 30 2533940' _publ_contact_author_phone '[+31] 30 2533902' loop_ _publ_author_name _publ_author_address 'Marsman, A.W.' ; Debye Institute Department of Physical Organic Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'van Walree, C.A.' ; Debye Institute Department of Physical Organic Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Havenith, R.W.A.' ; Debye Institute Department of Physical Organic Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Jenneskens, L.W.' ; Debye Institute Department of Physical Organic Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Lutz, M.' ; Bijvoet Center for Biomolecular Research Dep. Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Spek, A.L.' ; Bijvoet Center for Biomolecular Research Dep. Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Lutz, E.T.G.' ; Department of Vibrational Spectroscopy Utrecht University Sorbonnelaan 16 3584 CA Utrecht The Netherlands ; 'van der Maas, J.H.' ; Department of Vibrational Spectroscopy Utrecht University Sorbonnelaan 16 3584 CA Utrecht The Netherlands ; _publ_section_title ; Infinite, Undulating Chains of Intermolecularly Hydrogen Bonded EE-2,2-Dimethylcyclohexane-1,3-dione Bis-oximes in the Solid State. A Single Crystal X-ray, Charge Density and Spectroscopic Study. ; _journal_coden_Cambridge 188 # Compound 1 data_s1911d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H14 N2 O2' _chemical_formula_sum 'C8 H14 N2 O2' _chemical_formula_weight 170.21 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' '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 'P n m a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 10.0872(2) _cell_length_b 11.7970(2) _cell_length_c 7.7925(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 927.30(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _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 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8793 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1114 _reflns_number_gt 965 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'COLLECT data collection software, Nonius B.V., 1998.' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'manually editing of SHELXL results' _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1114 _refine_ls_number_parameters 80 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.324 _refine_ls_shift/su_mean 0.047 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 C3 C 0.26492(17) 0.14086(15) 0.2043(2) 0.0295(4) Uani 0.65 1 d PD . . H2 H 0.2349 0.0747 0.1364 0.035 Uiso 0.65 1 calc PR . . H3 H 0.3605 0.1313 0.2293 0.035 Uiso 0.65 1 calc PR . . C4 C 0.2429(2) 0.2500 0.1018(3) 0.0330(6) Uani 0.65 2 d SPD . . H4 H 0.3037 0.2500 0.0020 0.040 Uiso 0.65 2 calc SPR . . H5 H 0.1511 0.2500 0.0569 0.040 Uiso 0.65 2 calc SPR . . O O 0.08073(9) -0.01633(7) 0.31809(10) 0.0332(2) Uani 1 1 d . . . H1 H 0.0168(18) -0.0526(14) 0.376(2) 0.056(5) Uiso 1 1 d . . . N N 0.10557(8) 0.07580(7) 0.42974(11) 0.0230(2) Uani 1 1 d . . . C1 C 0.21831(13) 0.2500 0.48240(19) 0.0219(3) Uani 1 2 d SD . . C2 C 0.18777(10) 0.14734(8) 0.36986(13) 0.0230(2) Uani 1 1 d D . . C5 C 0.13836(16) 0.2500 0.64855(19) 0.0265(3) Uani 1 2 d S . . C6 C 0.36764(16) 0.2500 0.5305(3) 0.0367(4) Uani 1 2 d S . . H6 H 0.0461 0.2500 0.6211 0.050 Uiso 1 2 d S . . H7 H 0.1634 0.3155 0.7165 0.050 Uiso 1 1 d . . . H8 H 0.3892 0.3165 0.5982 0.050 Uiso 1 1 d . . . H9 H 0.4262 0.2500 0.4222 0.050 Uiso 1 2 d S . . C3A C 0.2248(3) 0.1426(2) 0.1792(4) 0.0255(6) Uani 0.35 1 d PD . . H2A H 0.2825 0.0761 0.1588 0.031 Uiso 0.35 1 calc PR . . H3A H 0.1432 0.1324 0.1103 0.031 Uiso 0.35 1 calc PR . . C4A C 0.2967(4) 0.2500 0.1188(6) 0.0273(9) Uani 0.35 2 d SPD . . H4A H 0.3020 0.2500 -0.0080 0.033 Uiso 0.35 2 calc SPR . . H5A H 0.3883 0.2500 0.1645 0.033 Uiso 0.35 2 calc SPR . . 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 C3 0.0262(8) 0.0307(9) 0.0316(9) -0.0078(7) 0.0113(6) -0.0020(6) C4 0.0290(12) 0.0498(16) 0.0203(11) 0.000 0.0035(9) 0.000 O 0.0413(5) 0.0246(4) 0.0338(5) -0.0110(3) 0.0080(3) -0.0094(3) N 0.0248(4) 0.0189(4) 0.0255(4) -0.0042(3) -0.0001(3) -0.0006(3) C1 0.0203(6) 0.0190(6) 0.0264(7) 0.000 -0.0007(5) 0.000 C2 0.0226(5) 0.0204(5) 0.0260(5) -0.0014(4) 0.0036(4) 0.0026(4) C5 0.0375(8) 0.0218(7) 0.0203(7) 0.000 -0.0002(6) 0.000 C6 0.0253(8) 0.0350(9) 0.0496(11) 0.000 -0.0107(7) 0.000 C3A 0.0193(12) 0.0244(14) 0.0330(16) -0.0049(12) 0.0072(11) 0.0014(10) C4A 0.025(2) 0.030(2) 0.027(2) 0.000 0.0022(16) 0.000 _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 C3 C2 1.5088(18) . ? C3 C4 1.531(2) . ? C3 H2 0.9900 . ? C3 H3 0.9900 . ? C4 C3 1.531(2) 8_565 ? C4 H4 0.9900 . ? C4 H5 0.9900 . ? O N 1.4146(11) . ? O H1 0.898(18) . ? N C2 1.2718(13) . ? C1 C5 1.525(2) . ? C1 C2 1.5267(13) 8_565 ? C1 C2 1.5267(13) . ? C1 C6 1.552(2) . ? C2 C3A 1.533(3) . ? C5 H6 0.9549 . ? C5 H7 0.9702 . ? C6 H8 0.9701 . ? C6 H9 1.0301 . ? C3A C4A 1.534(4) . ? C3A H2A 0.9900 . ? C3A H3A 0.9900 . ? C4A C3A 1.534(4) 8_565 ? C4A H4A 0.9900 . ? C4A H5A 0.9900 . ? 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 C3 C4 109.20(14) . . ? C2 C3 H2 109.8 . . ? C4 C3 H2 109.8 . . ? C2 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? H2 C3 H3 108.3 . . ? C3 C4 C3 114.5(2) 8_565 . ? C3 C4 H4 108.6 8_565 . ? C3 C4 H4 108.6 . . ? C3 C4 H5 108.6 8_565 . ? C3 C4 H5 108.6 . . ? H4 C4 H5 107.6 . . ? N O H1 100.5(10) . . ? C2 N O 113.56(8) . . ? C5 C1 C2 112.39(8) . 8_565 ? C5 C1 C2 112.39(8) . . ? C2 C1 C2 104.99(12) 8_565 . ? C5 C1 C6 107.95(13) . . ? C2 C1 C6 109.54(8) 8_565 . ? C2 C1 C6 109.54(8) . . ? N C2 C3 128.05(11) . . ? N C2 C1 116.57(10) . . ? C3 C2 C1 115.30(10) . . ? N C2 C3A 119.36(14) . . ? C3 C2 C3A 16.98(11) . . ? C1 C2 C3A 122.44(14) . . ? C1 C5 H6 109.0 . . ? C1 C5 H7 109.0 . . ? H6 C5 H7 112.1 . . ? C1 C6 H8 110.4 . . ? C1 C6 H9 111.0 . . ? H8 C6 H9 108.5 . . ? C4A C3A C2 112.5(2) . . ? C4A C3A H2A 109.1 . . ? C2 C3A H2A 109.1 . . ? C4A C3A H3A 109.1 . . ? C2 C3A H3A 109.1 . . ? H2A C3A H3A 107.8 . . ? C3A C4A C3A 111.4(3) . 8_565 ? C3A C4A H4A 109.4 . . ? C3A C4A H4A 109.4 8_565 . ? C3A C4A H5A 109.3 . . ? C3A C4A H5A 109.3 8_565 . ? H4A C4A H5A 108.0 . . ? 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 C2 C3 C4 C3 50.2(2) . . . 8_565 ? O N C2 C3 -4.10(17) . . . . ? O N C2 C1 179.29(8) . . . . ? O N C2 C3A 13.50(18) . . . . ? C4 C3 C2 N 127.46(15) . . . . ? C4 C3 C2 C1 -55.90(17) . . . . ? C4 C3 C2 C3A 63.0(4) . . . . ? C5 C1 C2 N -2.09(14) . . . . ? C2 C1 C2 N -124.54(9) 8_565 . . . ? C6 C1 C2 N 117.90(12) . . . . ? C5 C1 C2 C3 -179.13(11) . . . . ? C2 C1 C2 C3 58.41(15) 8_565 . . . ? C6 C1 C2 C3 -59.14(15) . . . . ? C5 C1 C2 C3A 163.23(16) . . . . ? C2 C1 C2 C3A 40.77(19) 8_565 . . . ? C6 C1 C2 C3A -76.78(18) . . . . ? N C2 C3A C4A 166.0(2) . . . . ? C3 C2 C3A C4A -68.6(4) . . . . ? C1 C2 C3A C4A 1.1(3) . . . . ? C2 C3A C4A C3A -47.5(4) . . . 8_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O H1 N 0.898(18) 1.970(18) 2.8080(12) 154.8(15) 5_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.272 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036 # Compound 2 data_s1983b _audit_creation_method XD _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 N2 O2' _chemical_formula_sum 'C10 H18 N2 O2' _chemical_formula_weight 198.26 _atom_type_scat_source 'International Tables Vol. IV Tables 2.2B and 2.3.1' _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 7.1363(2) _cell_length_b 7.2813(2) _cell_length_c 11.6544(3) _cell_angle_alpha 87.8805(18) _cell_angle_beta 72.1948(13) _cell_angle_gamma 82.7986(16) _cell_volume 572.03(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.31 _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; routine ABST in the PLATON package ; _exptl_special_details ; data merged with the SORTAV package ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_reflns_number 67635 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 50.14 _reflns_number_total 11896 _reflns_number_gt 7332 _reflns_threshold_expression 'I>3\s(I)' _computing_data_collection 'COLLECT data collection software, Nonius B.V., 1998.' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997), SORTAV (Blessing, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'XD (Koritsanszky et al., 1995)' _computing_molecular_graphics 'PLATON (Spek, 1998); XD (Koritsanszky et al., 1995)' _computing_publication_material ? _refine_ls_number_reflns 7332 _refine_ls_number_parameters 464 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0323 _refine_ls_wR_factor_gt 0.0281 _refine_ls_goodness_of_fit_ref 0.7211 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv O(1) 0.70083(8) 0.87407(9) 0.00008(5) 0.023 O(2) 0.19924(7) 0.35822(7) 0.46645(5) 0.021 N(1) 0.53232(5) 0.87500(4) 0.10109(3) 0.016 N(2) 0.19915(4) 0.53594(4) 0.41396(3) 0.016 C(1) 0.38565(4) 0.77205(4) 0.30320(2) 0.013 C(2) 0.55881(4) 0.77029(4) 0.18710(3) 0.014 C(3) 0.74918(4) 0.65135(5) 0.18228(3) 0.019 C(4) 0.71164(6) 0.44911(6) 0.21297(4) 0.017 C(5) 0.55955(4) 0.44531(4) 0.33889(3) 0.016 C(6) 0.37215(4) 0.57463(3) 0.35257(2) 0.013 C(7) 0.43397(7) 0.88638(4) 0.39805(3) 0.023 C(8) 0.19061(5) 0.86270(5) 0.28542(4) 0.022 C(9) 0.90492(6) 0.33384(7) 0.21630(4) 0.028 C(10) 0.63302(10) 0.36975(7) 0.11913(5) 0.034 H(1) 0.65120 0.96500 -0.05100 0.036 H(2) 0.06200 0.36970 0.52000 0.031 H(3) 0.81359 0.70292 0.24578 0.023 H(4) 0.85363 0.65770 0.09286 0.023 H(5) 0.52198 0.30563 0.35820 0.019 H(6) 0.62765 0.48197 0.40486 0.019 H(7) 0.57082 0.82395 0.41238 0.033 H(8) 0.31457 0.88802 0.48222 0.033 H(9) 0.44958 1.02675 0.36599 0.033 H(10) 0.07198 0.86040 0.36963 0.033 H(11) 0.15612 0.78650 0.21761 0.033 H(12) 0.20502 1.00438 0.25618 0.033 H(13) 0.87807 0.19118 0.23801 0.043 H(14) 0.95749 0.38882 0.28408 0.043 H(15) 1.01542 0.33850 0.12894 0.043 H(16) 0.49615 0.45170 0.11783 0.048 H(17) 0.60581 0.22798 0.14216 0.048 H(18) 0.74178 0.37346 0.03105 0.048 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0205(1) 0.0264(1) 0.0168(1) 0.0050(1) 0.0019(1) 0.0096(1) O(2) 0.0151(1) 0.0166(1) 0.0281(2) -0.0036(1) -0.0039(1) 0.0090(1) N(1) 0.01585(9) 0.01599(8) 0.01300(8) 0.00112(7) -.00181(7) 0.00503(7) N(2) 0.01155(9) 0.01484(8) 0.01931(10) -.00206(7) -.00307(7) 0.00566(7) C(1) 0.01332(8) 0.01147(8) 0.01266(9) 0.00006(6) -.00236(7) 0.00234(6) C(2) 0.01263(8) 0.01401(8) 0.01303(9) -.00064(7) -.00286(7) 0.00391(7) C(3) 0.01211(9) 0.02318(12) 0.01954(11) 0.00033(8) -.00223(8) 0.00826(9) C(4) 0.0170(1) 0.0174(1) 0.0140(1) 0.0052(1) -0.0031(1) 0.0006(1) C(5) 0.01418(9) 0.01382(8) 0.01595(9) 0.00141(6) -.00258(7) 0.00379(7) C(6) 0.01166(8) 0.01155(8) 0.01374(8) -.00089(5) -.00279(6) 0.00250(6) C(7) 0.0354(2) 0.0138(1) 0.0178(1) -0.0034(1) -0.0082(1) -0.0010(1) C(8) 0.0144(1) 0.0226(1) 0.0242(1) 0.0036(1) -0.0017(1) 0.0099(1) C(9) 0.0211(1) 0.0324(2) 0.0231(1) 0.0133(1) -0.0005(1) 0.0060(1) C(10) 0.0452(3) 0.0266(2) 0.0257(2) 0.0088(2) -0.0177(2) -0.0110(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) H(1) 0.9794(5) 1_555 1_555 yes O(2) H(2) 0.9824(5) 1_555 1_555 yes N(1) C(2) 1.2826(4) 1_555 1_555 yes N(2) C(6) 1.2835(4) 1_555 1_555 yes C(1) C(2) 1.5274(4) 1_555 1_555 yes C(1) C(6) 1.5318(3) 1_555 1_555 yes C(1) C(8) 1.5336(4) 1_555 1_555 yes C(2) C(3) 1.5036(4) 1_555 1_555 yes C(3) C(4) 1.5393(6) 1_555 1_555 yes C(3) H(3) 1.0825(4) 1_555 1_555 yes C(3) H(4) 1.0834(3) 1_555 1_555 yes C(4) C(5) 1.5372(5) 1_555 1_555 yes C(4) C(9) 1.5325(5) 1_555 1_555 yes C(4) C(10) 1.5323(7) 1_555 1_555 yes C(5) C(6) 1.5052(3) 1_555 1_555 yes C(5) H(5) 1.0824(3) 1_555 1_555 yes C(5) H(6) 1.0838(3) 1_555 1_555 yes C(7) H(7) 1.0822(5) 1_555 1_555 yes C(7) H(8) 1.0842(4) 1_555 1_555 yes C(7) H(9) 1.0824(3) 1_555 1_555 yes C(8) H(10) 1.0837(3) 1_555 1_555 yes C(8) H(11) 1.0856(5) 1_555 1_555 yes C(8) H(12) 1.0817(4) 1_555 1_555 yes C(9) H(13) 1.0865(5) 1_555 1_555 yes C(9) H(14) 1.0803(6) 1_555 1_555 yes C(9) H(15) 1.0830(4) 1_555 1_555 yes C(10) H(16) 1.0829(6) 1_555 1_555 yes C(10) H(17) 1.0831(6) 1_555 1_555 yes C(10) H(18) 1.0829(7) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) C(1) C(6) 109.3(1) 1_555 1_555 1_555 yes C(2) C(1) C(8) 112.0(1) 1_555 1_555 1_555 yes C(6) C(1) C(8) 112.7(1) 1_555 1_555 1_555 yes N(1) C(2) C(1) 117.1(1) 1_555 1_555 1_555 yes N(1) C(2) C(3) 124.5(1) 1_555 1_555 1_555 yes C(1) C(2) C(3) 118.3(1) 1_555 1_555 1_555 yes C(2) C(3) C(4) 110.6(1) 1_555 1_555 1_555 yes C(2) C(3) H(3) 109.6(1) 1_555 1_555 1_555 yes C(2) C(3) H(4) 109.6(1) 1_555 1_555 1_555 yes C(4) C(3) H(3) 109.4(1) 1_555 1_555 1_555 yes C(4) C(3) H(4) 109.5(1) 1_555 1_555 1_555 yes H(3) C(3) H(4) 108.1(1) 1_555 1_555 1_555 yes C(3) C(4) C(5) 108.2(1) 1_555 1_555 1_555 yes C(3) C(4) C(9) 109.5(1) 1_555 1_555 1_555 yes C(3) C(4) C(10) 110.2(1) 1_555 1_555 1_555 yes C(5) C(4) C(9) 108.5(1) 1_555 1_555 1_555 yes C(5) C(4) C(10) 110.3(1) 1_555 1_555 1_555 yes C(9) C(4) C(10) 110.1(1) 1_555 1_555 1_555 yes C(4) C(5) C(6) 113.8(1) 1_555 1_555 1_555 yes C(4) C(5) H(5) 108.9(1) 1_555 1_555 1_555 yes C(4) C(5) H(6) 108.6(1) 1_555 1_555 1_555 yes C(6) C(5) H(5) 108.9(1) 1_555 1_555 1_555 yes C(6) C(5) H(6) 108.8(1) 1_555 1_555 1_555 yes H(5) C(5) H(6) 107.7(1) 1_555 1_555 1_555 yes N(2) C(6) C(1) 116.6(1) 1_555 1_555 1_555 yes N(2) C(6) C(5) 123.7(1) 1_555 1_555 1_555 yes C(1) C(6) C(5) 119.4(1) 1_555 1_555 1_555 yes H(7) C(7) H(8) 109.5(1) 1_555 1_555 1_555 yes H(7) C(7) H(9) 109.6(1) 1_555 1_555 1_555 yes H(8) C(7) H(9) 109.4(1) 1_555 1_555 1_555 yes C(1) C(8) H(10) 109.6(1) 1_555 1_555 1_555 yes C(1) C(8) H(11) 109.4(1) 1_555 1_555 1_555 yes C(1) C(8) H(12) 109.7(1) 1_555 1_555 1_555 yes H(10) C(8) H(11) 109.2(1) 1_555 1_555 1_555 yes H(10) C(8) H(12) 109.5(1) 1_555 1_555 1_555 yes H(11) C(8) H(12) 109.4(1) 1_555 1_555 1_555 yes C(4) C(9) H(13) 109.4(1) 1_555 1_555 1_555 yes C(4) C(9) H(14) 109.6(1) 1_555 1_555 1_555 yes C(4) C(9) H(15) 109.5(1) 1_555 1_555 1_555 yes H(13) C(9) H(14) 109.4(1) 1_555 1_555 1_555 yes H(13) C(9) H(15) 109.2(1) 1_555 1_555 1_555 yes H(14) C(9) H(15) 109.7(1) 1_555 1_555 1_555 yes C(4) C(10) H(16) 109.5(1) 1_555 1_555 1_555 yes C(4) C(10) H(17) 109.5(1) 1_555 1_555 1_555 yes C(4) C(10) H(18) 109.4(1) 1_555 1_555 1_555 yes H(16) C(10) H(17) 109.5(1) 1_555 1_555 1_555 yes H(16) C(10) H(18) 109.5(1) 1_555 1_555 1_555 yes H(17) C(10) H(18) 109.5(1) 1_555 1_555 1_555 yes 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 C(6) C(1) C(2) N(1) 140.2(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) N(2) -151.0(1) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(2) C(3) -41.5(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) 35.5(1) 1_555 1_555 1_555 1_555 yes C(8) C(1) C(2) N(1) 14.6(1) 1_555 1_555 1_555 1_555 yes C(8) C(1) C(2) C(3) -167.1(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) H(10) 179.7(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) H(11) 60.0(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) H(12) -60.0(1) 1_555 1_555 1_555 1_555 yes C(8) C(1) C(6) N(2) -25.7(1) 1_555 1_555 1_555 1_555 yes C(8) C(1) C(6) C(5) 160.7(1) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(8) H(10) 56.0(1) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(8) H(11) -63.7(1) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(8) H(12) 176.3(1) 1_555 1_555 1_555 1_555 yes N(1) C(2) C(3) C(4) -126.3(1) 1_555 1_555 1_555 1_555 yes N(1) C(2) C(3) H(3) 112.9(1) 1_555 1_555 1_555 1_555 yes N(1) C(2) C(3) H(4) -5.6(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 55.5(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) H(3) -65.3(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) H(4) 176.3(1) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) -57.9(1) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(9) -176.0(1) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(10) 62.8(1) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(5) 63.0(1) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(9) -55.1(1) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(10) -176.3(1) 1_555 1_555 1_555 1_555 yes H(4) C(3) C(4) C(5) -178.7(1) 1_555 1_555 1_555 1_555 yes H(4) C(3) C(4) C(9) 63.2(1) 1_555 1_555 1_555 1_555 yes H(4) C(3) C(4) C(10) -58.0(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 53.3(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) H(5) 175.0(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) H(6) -68.1(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(9) H(13) 180.0(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(9) H(14) 60.0(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(9) H(15) -60.4(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(10) H(16) -59.4(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(10) H(17) -179.4(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(10) H(18) 60.6(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(5) C(6) 172.0(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(5) H(5) -66.3(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(5) H(6) 50.7(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(9) H(13) 62.1(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(9) H(14) -57.9(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(9) H(15) -178.2(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(5) C(6) -67.3(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(5) H(5) 54.4(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(5) H(6) 171.4(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(10) H(16) 60.0(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(10) H(17) -60.1(1) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(10) H(18) 180.0(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(9) H(13) -58.7(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(9) H(14) -178.7(1) 1_555 1_555 1_555 1_555 yes C(10) C(4) C(9) H(15) 60.9(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(10) H(16) 179.7(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(10) H(17) 59.7(1) 1_555 1_555 1_555 1_555 yes C(9) C(4) C(10) H(18) -60.3(1) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) N(2) 142.5(1) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(1) -44.5(1) 1_555 1_555 1_555 1_555 yes H(5) C(5) C(6) N(2) 20.8(1) 1_555 1_555 1_555 1_555 yes H(5) C(5) C(6) C(1) -166.2(1) 1_555 1_555 1_555 1_555 yes H(6) C(5) C(6) N(2) -96.3(1) 1_555 1_555 1_555 1_555 yes H(6) C(5) C(6) C(1) 76.7(1) 1_555 1_555 1_555 1_555 yes _refine_diff_density_max 0.197 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.026 _refine_ls_shift/su_max 0.0041