# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_rep _database_code_CSD 176579 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Shuto, Satoshi' 'Kamiyama, Noriko' 'Kazuta, Yuji' 'Kohsaka, Shinich' 'Matsuda, Akira' 'Mochizuki, Daisuke' 'Ohmori, Yutaka' 'Tsujita, Ryuichi' 'Uchino, Shigeo' 'Yamashita, Kanako' 'Yamashita, Akitake' _publ_contact_author_name 'Dr Satoshi Shuto' _publ_contact_author_address ; Gradute School of Pharmaceutical Sciences, Hokkaido University Kita-12 Nishi-6 Kita-Ku Sapporo 060-0812 JAPAN ; _publ_contact_author_email 'SHU@PHARM.HOKUDAI.AC.JP' _publ_section_title ; Synthesis of (1S,2R)-1-Phenyl-2-[(S)-1-aminoalkyl]-N,N-diethylcyclopropanecarboxamides as Novel NMDA Receptor Antagonists having a Unique NMDA Receptor Subtypes selectivity ; _publ_section_abstract ; We present the crystal and molecular structure of Compound 15 [(1S,2R)-1-Phenyl-2-[(R)-aminocyclopropylmethyl]-N, N-diethylcyclopropanecarboxamide Hydrochloride]. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using maXus (MacScience, Japan). ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prizm' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _chemical_formula_sum 'C18 H27 Cl1 N2 O1 ' _chemical_formula_weight 322.90 _cell_length_a 23.900(4) _cell_length_b 6.065(2) _cell_length_c 16.073(3) _cell_angle_alpha 90.000000(0) _cell_angle_beta 128.08(1) _cell_angle_gamma 90.000000(0) _cell_volume 1833.8(7) _cell_measurement_reflns_used '24' _cell_measurement_theta_min '26.5' _cell_measurement_theta_max '30.0' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_meas 1.170 _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.86 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.999 _cell_measurement_temperature '298' _exptl_absorpt_correction_type 'empirical' _diffrn_reflns_number 1620 _reflns_number_total 1513 _reflns_number_observed 1508 _reflns_observed_criterion 'refl_observed_if_I_>_0.00_sigma(I)' _diffrn_reflns_theta_max 49.65 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.024 _refine_ls_wR_factor_obs 0.055 _refine_ls_hydrogen_treatment 'refall' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(1) _refine_ls_number_reflns 1508 _refine_ls_number_parameters 307 _refine_ls_goodness_of_fit_obs 2.500 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0668 _refine_ls_shift/esd_mean 0.0038 _refine_diff_density_min -0.09 _refine_diff_density_max 0.10 _refine_ls_extinction_method 'None' _atom_type_scat_source 'D.Waasmaier&A.Kirfel,Acta Cryst.1995,A51, 416-431' _computing_data_reduction 'maXus' _computing_molecular_graphics 'maXus' _computing_publication_material 'maXus' _computing_structure_refinement 'maXus' _computing_structure_solution 'maXus' _diffrn_measurement_device 'Mac Science MXC18' _computing_cell_refinement 'MXC(MAC Science)' _diffrn_measurement_method 'theta/2theta' _computing_data_collection 'MXC(MAC Science)' _diffrn_radiation_type 'Cu-Ka' _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_radiation_wavelength 1.54178 _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.00047 _diffrn_orient_matrix_UB_12 0.03505 _diffrn_orient_matrix_UB_13 0.06038 _diffrn_orient_matrix_UB_21 -0.05296 _diffrn_orient_matrix_UB_22 0.01348 _diffrn_orient_matrix_UB_23 -0.05022 _diffrn_orient_matrix_UB_31 -0.00455 _diffrn_orient_matrix_UB_32 -0.16057 _diffrn_orient_matrix_UB_33 0.00891 _cell_formula_units_Z 4 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z +X+0.5,+Y+0.5,+Z -X,+Y,-Z -X+0.5,+Y+0.5,-Z _symmetry_space_group_name_H-M 'C 2' _symmetry_cell_setting 'Monoclinic' _diffrn_reflns_av_R_equivalents 0.028 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type Cl1 -0.29132(1) 0.19400 -0.13607(1) 0.05564(9) 1.00 Uij N19 -0.60226(3) -0.1847(1) -0.29968(5) 0.0562(3) 1.00 Uij O21 -0.53352(3) 0.1065(1) -0.26817(5) 0.0874(3) 1.00 Uij N20 -0.33001(2) -0.3106(2) -0.11179(4) 0.0478(3) 1.00 Uij C8 -0.57786(3) -0.2902(2) -0.45897(4) 0.0466(4) 1.00 Uij C7 -0.52277(3) -0.2046(1) -0.34830(4) 0.0438(3) 1.00 Uij C9 -0.57696(4) -0.5003(1) -0.49229(5) 0.0580(4) 1.00 Uij C5 -0.45037(3) -0.3134(2) -0.27543(4) 0.0488(4) 1.00 Uij C6 -0.45810(4) -0.1015(2) -0.32916(5) 0.0581(4) 1.00 Uij C4 -0.40718(3) -0.3160(2) -0.15651(4) 0.0459(4) 1.00 Uij C11 -0.68075(4) -0.4161(2) -0.66868(6) 0.0641(4) 1.00 Uij C14 -0.55226(3) -0.0837(1) -0.30017(5) 0.0483(3) 1.00 Uij C3 -0.42005(4) -0.5162(1) -0.11562(6) 0.0603(4) 1.00 Uij C10 -0.62868(4) -0.5614(2) -0.59796(6) 0.0710(4) 1.00 Uij C13 -0.63066(4) -0.1437(1) -0.53210(5) 0.0551(4) 1.00 Uij C15 -0.63895(5) -0.0565(2) -0.26869(8) 0.0886(5) 1.00 Uij C17 -0.61848(4) -0.4202(1) -0.31761(6) 0.0582(4) 1.00 Uij C12 -0.68212(4) -0.2064(2) -0.63668(6) 0.0648(4) 1.00 Uij C18 -0.69220(5) -0.4726(2) -0.41839(8) 0.0831(5) 1.00 Uij C2 -0.46079(5) -0.5008(2) -0.07365(7) 0.0822(5) 1.00 Uij C1 -0.38334(5) -0.5420(2) 0.00018(7) 0.0887(6) 1.00 Uij C16 -0.6033(1) -0.0617(3) -0.1531(1) 0.148(1) 1.00 Uij H20A -0.3022(3) -0.297(2) -0.0404(6) 0.051(2) 1.00 Uiso H20B -0.3218(4) -0.187(2) -0.1341(6) 0.038(2) 1.00 Uiso H20C -0.3188(6) -0.448(2) -0.1275(9) 0.080(3) 1.00 Uiso H2A -0.4738(4) -0.360(2) -0.0680(6) 0.050(2) 1.00 Uiso H17A -0.6091(4) -0.475(2) -0.2531(7) 0.054(2) 1.00 Uiso H6A -0.4396(4) 0.029(1) -0.2866(6) 0.051(2) 1.00 Uiso H5 -0.4429(3) -0.440(1) -0.2993(5) 0.030(2) 1.00 Uiso H9 -0.5392(4) -0.605(2) -0.4391(6) 0.060(2) 1.00 Uiso H2B -0.4970(5) -0.634(2) -0.0942(7) 0.078(3) 1.00 Uiso H13 -0.6309(4) -0.007(2) -0.5076(6) 0.051(2) 1.00 Uiso H17B -0.5817(4) -0.493(1) -0.3123(6) 0.043(2) 1.00 Uiso H18A -0.7014(6) -0.617(2) -0.4221(9) 0.101(4) 1.00 Uiso H18B -0.7282(5) -0.411(2) -0.4179(8) 0.086(3) 1.00 Uiso H3 -0.4270(5) -0.658(2) -0.1498(7) 0.069(3) 1.00 Uiso H4 -0.4126(3) -0.191(1) -0.1280(5) 0.029(2) 1.00 Uiso H6B -0.4552(4) -0.109(2) -0.3851(7) 0.078(3) 1.00 Uiso H1A -0.3670(6) -0.683(2) 0.0223(9) 0.089(4) 1.00 Uiso H1B -0.3539(5) -0.427(2) 0.0418(8) 0.080(3) 1.00 Uiso H11 -0.7200(5) -0.465(2) -0.7454(7) 0.080(3) 1.00 Uiso H12 -0.7210(5) -0.087(2) -0.6845(7) 0.084(3) 1.00 Uiso H10 -0.6246(5) -0.715(2) -0.6158(8) 0.089(3) 1.00 Uiso H15A -0.6377(6) 0.099(2) -0.2851(8) 0.091(3) 1.00 Uiso H15B -0.6910(6) -0.130(2) -0.3102(8) 0.097(3) 1.00 Uiso H18C -0.6978(5) -0.415(2) -0.4820(8) 0.088(3) 1.00 Uiso H16A -0.5558(6) -0.010(2) -0.1155(9) 0.094(4) 1.00 Uiso H16B -0.6427(8) 0.038(3) -0.150(1) 0.161(6) 1.00 Uiso H16C -0.5969(9) -0.208(3) -0.128(1) 0.157(7) 1.00 Uiso 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 Cl1 0.04671(7) 0.04238(8) 0.04036(7) 0.00185(9) 0.01606(6) 0.00301(8) N19 0.0470(3) 0.0377(3) 0.0547(3) 0.0032(3) 0.0334(3) -.0006(3) O21 0.0721(3) 0.0386(3) 0.0980(4) -.0118(3) 0.0513(3) -.0246(3) N20 0.0373(2) 0.0402(3) 0.0370(2) -.0024(3) 0.0166(2) 0.0023(3) C8 0.0356(3) 0.0443(3) 0.0368(3) -.0057(3) 0.0215(2) -.0036(3) C7 0.0344(3) 0.0355(3) 0.0366(3) -.0020(3) 0.0189(3) -.0009(3) C9 0.0509(4) 0.0464(4) 0.0436(3) -.0019(3) 0.0252(3) -.0043(3) C5 0.0344(3) 0.0504(3) 0.0375(3) 0.0021(4) 0.0202(2) -.0040(4) C6 0.0417(3) 0.0644(5) 0.0396(3) -.0075(3) 0.0216(3) 0.0031(4) C4 0.0375(3) 0.0382(3) 0.0367(3) 0.0001(3) 0.0203(2) -.0057(4) C11 0.0482(4) 0.0786(5) 0.0368(4) -.0134(4) 0.0235(3) -.0095(4) C14 0.0410(3) 0.0334(3) 0.0408(3) 0.0018(3) 0.0207(3) -.0027(3) C3 0.0510(3) 0.0460(4) 0.0509(4) -.0092(3) 0.0297(3) -.0039(3) C10 0.0675(5) 0.0575(5) 0.0515(4) -.0140(4) 0.0367(4) -.0156(4) C13 0.0423(3) 0.0523(4) 0.0421(3) 0.0022(3) 0.0234(3) 0.0005(3) C15 0.0760(5) 0.0661(6) 0.0843(6) 0.0207(5) 0.0594(5) 0.0067(5) C17 0.0459(4) 0.0446(4) 0.0524(4) -.0030(3) 0.0286(3) 0.0055(3) C12 0.0434(4) 0.0806(5) 0.0404(4) 0.0041(4) 0.0215(3) 0.0076(4) C18 0.0529(4) 0.0762(6) 0.0719(5) -.0202(5) 0.0283(4) 0.0091(5) C2 0.0615(5) 0.0938(7) 0.0574(4) -.0124(5) 0.0391(4) -.0003(5) C1 0.0598(5) 0.1054(8) 0.0569(5) -.0133(6) 0.0275(4) 0.0230(6) C16 0.155(1) 0.126(1) 0.1050(9) 0.042(1) 0.101(1) 0.007(1) 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 C15 N19 C14 O21 5.3(1) . . . . ? C15 N19 C14 C7 -170.6(1) . . . . ? C14 N19 C15 C16 -89.6(2) . . . . ? C17 N19 C14 O21 -168.2(2) . . . . ? C17 N19 C14 C7 15.9(1) . . . . ? C14 N19 C17 C18 -114.1(1) . . . . ? C15 N19 C17 C18 72.2(1) . . . . ? C17 N19 C15 C16 84.6(2) . . . . ? C9 C8 C7 C5 19.8(1) . . . . ? C9 C8 C7 C6 87.3(1) . . . . ? C9 C8 C7 C14 -134.4(1) . . . . ? C7 C8 C9 C10 -177.1(2) . . . . ? C13 C8 C7 C5 -157.4(1) . . . . ? C13 C8 C7 C6 -89.8(1) . . . . ? C13 C8 C7 C14 48.5(1) . . . . ? C7 C8 C13 C12 177.8(2) . . . . ? C13 C8 C9 C10 0.0(1) . . . . ? C9 C8 C13 C12 0.5(1) . . . . ? C8 C7 C5 C6 102.4(1) . . . . ? C8 C7 C5 C4 -150.5(1) . . . . ? C8 C7 C6 C5 -112.2(1) . . . . ? C8 C7 C14 N19 52.6(1) . . . . ? C8 C7 C14 O21 -123.3(1) . . . . ? C5 C7 C6 C5 0.0(1) . . . . ? C6 C7 C5 C6 0.0(1) . . . . ? C6 C7 C5 C4 107.1(1) . . . . ? C5 C7 C14 N19 -102.1(1) . . . . ? C5 C7 C14 O21 82.0(1) . . . . ? C14 C7 C5 C6 -104.3(1) . . . . ? C14 C7 C5 C4 2.7(1) . . . . ? C6 C7 C14 N19 -169.5(1) . . . . ? C6 C7 C14 O21 14.6(1) . . . . ? C14 C7 C6 C5 109.7(1) . . . . ? C8 C9 C10 C11 -0.7(1) . . . . ? C7 C5 C6 C7 0.0(1) . . . . ? C7 C5 C4 N20 -147.7(1) . . . . ? C7 C5 C4 C3 92.2(1) . . . . ? C6 C5 C4 N20 -76.1(1) . . . . ? C4 C5 C6 C7 -113.7(1) . . . . ? C6 C5 C4 C3 163.7(1) . . . . ? N20 C4 C3 C2 133.8(1) . . . . ? N20 C4 C3 C1 63.4(1) . . . . ? C5 C4 C3 C2 -107.7(1) . . . . ? C5 C4 C3 C1 -178.0(2) . . . . ? C12 C11 C10 C9 0.9(1) . . . . ? C10 C11 C12 C13 -0.4(1) . . . . ? C4 C3 C2 C1 -109.4(1) . . . . ? C4 C3 C1 C2 110.2(1) . . . . ? C2 C3 C1 C2 0.0(1) . . . . ? C1 C3 C2 C1 0.0(1) . . . . ? C8 C13 C12 C11 -0.3(1) . . . . ? C3 C2 C1 C3 0.0(1) . . . . ? C14 N19 C15 H15A 26.6(7) . . . . ? C14 N19 C15 H15B 151.2(7) . . . . ? C14 N19 C17 H17A 119.3(6) . . . . ? C14 N19 C17 H17B 14.1(6) . . . . ? C15 N19 C17 H17A -54.4(6) . . . . ? C15 N19 C17 H17B -159.6(6) . . . . ? C17 N19 C15 H15A -159.2(7) . . . . ? C17 N19 C15 H15B -34.7(7) . . . . ? H20A N20 C4 C5 173.7(6) . . . . ? H20A N20 C4 C3 -63.5(6) . . . . ? H20A N20 C4 H4 52.2(8) . . . . ? H20B N20 C4 C5 59.7(6) . . . . ? H20B N20 C4 C3 -177.5(6) . . . . ? H20B N20 C4 H4 -61.9(7) . . . . ? H20C N20 C4 C5 -68.8(8) . . . . ? H20C N20 C4 C3 54.0(8) . . . . ? H20C N20 C4 H4 169.6(9) . . . . ? C7 C8 C9 H9 3.6(6) . . . . ? C7 C8 C13 H13 -4.6(6) . . . . ? C13 C8 C9 H9 -179.3(6) . . . . ? C9 C8 C13 H13 178.1(6) . . . . ? C8 C7 C5 H5 -5.2(5) . . . . ? C8 C7 C6 H6A 139.8(6) . . . . ? C8 C7 C6 H6B -4.9(7) . . . . ? C5 C7 C6 H6A -108.0(6) . . . . ? C6 C7 C5 H5 -107.7(5) . . . . ? C5 C7 C6 H6B 107.4(7) . . . . ? C14 C7 C5 H5 148.0(5) . . . . ? C14 C7 C6 H6A 1.7(6) . . . . ? C14 C7 C6 H6B -142.9(7) . . . . ? C8 C9 C10 H10 -179.8(7) . . . . ? H9 C9 C10 C11 178.6(6) . . . . ? H9 C9 C10 H10 -0.5(9) . . . . ? C7 C5 C6 H6A 106.8(6) . . . . ? C7 C5 C6 H6B -107.2(7) . . . . ? C7 C5 C4 H4 -33.1(5) . . . . ? C4 C5 C6 H6A -6.8(6) . . . . ? C6 C5 C4 H4 38.5(5) . . . . ? C4 C5 C6 H6B 139.2(7) . . . . ? H5 C5 C6 C7 107.6(5) . . . . ? H5 C5 C6 H6A -145.6(8) . . . . ? H5 C5 C6 H6B 0.4(8) . . . . ? H5 C5 C4 N20 65.1(5) . . . . ? H5 C5 C4 C3 -55.0(5) . . . . ? H5 C5 C4 H4 179.7(7) . . . . ? N20 C4 C3 H3 -80.7(7) . . . . ? C5 C4 C3 H3 37.8(7) . . . . ? H4 C4 C3 C2 20.8(5) . . . . ? H4 C4 C3 C1 -49.5(5) . . . . ? H4 C4 C3 H3 166.4(8) . . . . ? C10 C11 C12 H12 -177.3(7) . . . . ? C12 C11 C10 H10 179.9(8) . . . . ? H11 C11 C10 C9 -177.1(7) . . . . ? H11 C11 C10 H10 1.9(10) . . . . ? H11 C11 C12 C13 177.6(7) . . . . ? H11 C11 C12 H12 0.7(10) . . . . ? C4 C3 C2 H2A -5.8(6) . . . . ? C4 C3 C2 H2B 140.0(6) . . . . ? C4 C3 C1 H1A -137.0(8) . . . . ? C4 C3 C1 H1B 0.8(8) . . . . ? C1 C3 C2 H2A 103.6(6) . . . . ? C1 C3 C2 H2B -110.6(6) . . . . ? C2 C3 C1 H1A 112.8(8) . . . . ? C2 C3 C1 H1B -109.5(8) . . . . ? H3 C3 C2 C1 103.1(6) . . . . ? H3 C3 C2 H2A -153.3(9) . . . . ? H3 C3 C2 H2B -7.5(9) . . . . ? H3 C3 C1 C2 -103.5(6) . . . . ? H3 C3 C1 H1A 9.3(10) . . . . ? H3 C3 C1 H1B 147.0(10) . . . . ? C8 C13 C12 H12 176.9(7) . . . . ? H13 C13 C12 C11 -177.8(7) . . . . ? H13 C13 C12 H12 -0.6(9) . . . . ? N19 C15 C16 H16A 57.0(8) . . . . ? N19 C15 C16 H16B -176.6(8) . . . . ? N19 C15 C16 H16C -56.1(11) . . . . ? H15A C15 C16 H16A -60.2(11) . . . . ? H15A C15 C16 H16B 66.3(11) . . . . ? H15A C15 C16 H16C -173.2(13) . . . . ? H15B C15 C16 H16A 174.7(11) . . . . ? H15B C15 C16 H16B -58.8(11) . . . . ? H15B C15 C16 H16C 61.7(13) . . . . ? N19 C17 C18 H18A -173.6(9) . . . . ? N19 C17 C18 H18B -61.2(7) . . . . ? N19 C17 C18 H18C 59.9(7) . . . . ? H17A C17 C18 H18A -52.1(11) . . . . ? H17A C17 C18 H18B 60.4(9) . . . . ? H17A C17 C18 H18C -178.5(9) . . . . ? H17B C17 C18 H18A 60.7(11) . . . . ? H17B C17 C18 H18B 173.2(9) . . . . ? H17B C17 C18 H18C -65.7(9) . . . . ? C3 C2 C1 H1A -98.9(9) . . . . ? C3 C2 C1 H1B 104.2(8) . . . . ? H2A C2 C1 C3 -108.5(6) . . . . ? H2A C2 C1 H1A 152.6(11) . . . . ? H2A C2 C1 H1B -4.3(10) . . . . ? H2B C2 C1 C3 105.2(7) . . . . ? H2B C2 C1 H1A 6.3(11) . . . . ? H2B C2 C1 H1B -150.6(10) . . . . ? 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 N19 C14 1.347(1) . . ? N19 C15 1.470(2) . . ? N19 C17 1.462(2) . . ? O21 C14 1.229(1) . . ? N20 C4 1.511(1) . . ? C8 C7 1.510(1) . . ? C8 C9 1.388(2) . . ? C8 C13 1.390(2) . . ? C7 C5 1.517(1) . . ? C7 C6 1.512(1) . . ? C7 C14 1.518(1) . . ? C9 C10 1.400(2) . . ? C5 C6 1.495(2) . . ? C5 C4 1.512(1) . . ? C4 C3 1.500(2) . . ? C11 C10 1.368(2) . . ? C11 C12 1.380(2) . . ? C3 C2 1.491(2) . . ? C3 C1 1.498(2) . . ? C13 C12 1.390(2) . . ? C15 C16 1.491(2) . . ? C17 C18 1.519(2) . . ? C2 C1 1.479(2) . . ? N20 H20A 0.909(8) . . ? N20 H20B 0.903(9) . . ? N20 H20C 0.95(2) . . ? C9 H9 0.999(9) . . ? C5 H5 0.926(8) . . ? C6 H6A 0.960(9) . . ? C6 H6B 0.944(9) . . ? C4 H4 0.937(7) . . ? C11 H11 1.03(1) . . ? C3 H3 0.98(2) . . ? C10 H10 1.00(2) . . ? C13 H13 0.92(1) . . ? C15 H15A 0.99(2) . . ? C15 H15B 1.08(2) . . ? C17 H17A 0.974(9) . . ? C17 H17B 0.940(8) . . ? C12 H12 1.05(2) . . ? C18 H18A 0.90(2) . . ? C18 H18B 0.94(2) . . ? C18 H18C 1.01(2) . . ? C2 H2A 0.93(1) . . ? C2 H2B 1.08(2) . . ? C1 H1A 0.91(2) . . ? C1 H1B 0.92(2) . . ? C16 H16A 0.95(2) . . ? C16 H16B 1.15(2) . . ? C16 H16C 0.95(2) . . ? 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 C14 N19 C15 118.6(1) . . . ? C14 N19 C17 124.9(1) . . . ? C15 N19 C17 116.3(1) . . . ? C7 C8 C9 124.1(1) . . . ? C7 C8 C13 117.0(1) . . . ? C9 C8 C13 118.8(1) . . . ? C8 C7 C5 120.7(1) . . . ? C8 C7 C6 114.9(1) . . . ? C8 C7 C14 115.1(1) . . . ? C5 C7 C6 59.1(1) . . . ? C5 C7 C14 118.9(1) . . . ? C6 C7 C14 115.7(1) . . . ? C8 C9 C10 119.9(1) . . . ? C7 C5 C6 60.3(1) . . . ? C7 C5 C4 123.0(1) . . . ? C6 C5 C4 119.0(1) . . . ? C7 C6 C5 60.6(1) . . . ? N20 C4 C5 106.4(1) . . . ? N20 C4 C3 109.2(1) . . . ? C5 C4 C3 113.4(1) . . . ? C10 C11 C12 120.2(1) . . . ? N19 C14 O21 121.3(1) . . . ? N19 C14 C7 118.4(1) . . . ? O21 C14 C7 120.2(1) . . . ? C4 C3 C2 121.0(1) . . . ? C4 C3 C1 120.5(1) . . . ? C2 C3 C1 59.3(1) . . . ? C9 C10 C11 120.5(1) . . . ? C8 C13 C12 120.8(1) . . . ? N19 C15 C16 114.1(2) . . . ? N19 C17 C18 114.0(1) . . . ? C11 C12 C13 119.7(1) . . . ? C3 C2 C1 60.6(1) . . . ? C3 C1 C2 60.1(1) . . . ? C4 N20 H20A 109.2(5) . . . ? C4 N20 H20B 109.2(5) . . . ? C4 N20 H20C 108.3(7) . . . ? H20A N20 H20B 104.8(9) . . . ? H20A N20 H20C 108.1(10) . . . ? H20B N20 H20C 117.1(9) . . . ? C8 C9 H9 118.4(6) . . . ? C10 C9 H9 121.7(6) . . . ? C7 C5 H5 117.5(5) . . . ? C6 C5 H5 117.6(5) . . . ? C4 C5 H5 111.1(5) . . . ? C7 C6 H6A 116.7(5) . . . ? C7 C6 H6B 116.9(6) . . . ? C5 C6 H6A 117.5(5) . . . ? C5 C6 H6B 117.0(7) . . . ? H6A C6 H6B 116.5(8) . . . ? N20 C4 H4 104.2(4) . . . ? C5 C4 H4 114.7(5) . . . ? C3 C4 H4 108.4(5) . . . ? C10 C11 H11 120.0(6) . . . ? C12 C11 H11 119.8(6) . . . ? C4 C3 H3 118.4(6) . . . ? C2 C3 H3 112.1(6) . . . ? C1 C3 H3 111.8(6) . . . ? C9 C10 H10 115.2(6) . . . ? C11 C10 H10 124.3(6) . . . ? C8 C13 H13 117.2(5) . . . ? C12 C13 H13 121.9(5) . . . ? N19 C15 H15A 107.0(7) . . . ? N19 C15 H15B 105.9(7) . . . ? C16 C15 H15A 105.4(7) . . . ? C16 C15 H15B 108.5(6) . . . ? H15A C15 H15B 116.2(9) . . . ? N19 C17 H17A 105.4(6) . . . ? N19 C17 H17B 108.9(6) . . . ? C18 C17 H17A 114.7(5) . . . ? C18 C17 H17B 113.8(5) . . . ? H17A C17 H17B 98.8(7) . . . ? C11 C12 H12 125.2(6) . . . ? C13 C12 H12 115.0(6) . . . ? C17 C18 H18A 110.5(8) . . . ? C17 C18 H18B 111.8(7) . . . ? C17 C18 H18C 110.5(6) . . . ? H18A C18 H18B 101.6(11) . . . ? H18A C18 H18C 113.5(10) . . . ? H18B C18 H18C 108.6(9) . . . ? C3 C2 H2A 116.8(5) . . . ? C3 C2 H2B 116.1(6) . . . ? C1 C2 H2A 113.9(5) . . . ? C1 C2 H2B 119.4(6) . . . ? H2A C2 H2B 117.6(8) . . . ? C3 C1 H1A 111.3(8) . . . ? C3 C1 H1B 115.0(7) . . . ? C2 C1 H1A 119.6(8) . . . ? C2 C1 H1B 118.2(7) . . . ? H1A C1 H1B 118.2(10) . . . ? C15 C16 H16A 109.0(7) . . . ? C15 C16 H16B 101.0(8) . . . ? C15 C16 H16C 111.8(10) . . . ? H16A C16 H16B 119.3(12) . . . ? H16A C16 H16C 102.9(13) . . . ? H16B C16 H16C 113.1(13) . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 N20 3.2372 1_555 1_565 ? Cl1 N20 3.1673 1_555 4_455 ? Cl1 C11 3.6471 1_555 3_464 ? Cl1 C3 3.7297 1_555 1_565 ? Cl1 C10 3.7482 1_555 3_464 ? Cl1 C1 3.606(1) 1_555 4_455 ? Cl1 H20A 2.285(7) 1_555 4_455 ? Cl1 H20C 2.30(1) 1_555 1_565 ? Cl1 H1B 2.897(9) 1_555 4_455 ? Cl1 H11 2.935(9) 1_555 3_464 ? O21 C3 3.225(1) 1_555 1_565 ? O21 C17 3.317(1) 1_555 1_565 ? O21 C2 3.430(1) 1_555 1_565 ? O21 H17B 2.591(9) 1_555 1_565 ? O21 H3 2.483(9) 1_555 1_565 ? C9 C9 3.837(1) 1_555 3_454 ? C5 C11 3.8063 1_555 3_454 ? C5 C10 3.836(1) 1_555 3_454 ? C6 C11 3.847(1) 1_555 3_454 ? C6 C13 3.9209 1_555 3_454 ? C6 C12 3.769(1) 1_555 3_454 ? C11 C15 3.867(1) 1_555 4_344 ? C11 H15B 3.15(1) 1_555 4_344 ? C10 C13 3.696(1) 1_555 1_545 ? C10 H5 3.111(7) 1_555 3_454 ? C10 H13 3.083(9) 1_555 1_545 ? C13 C18 3.934(1) 1_555 4_354 ? C13 H6B 3.066(9) 1_555 3_454 ? C13 H10 2.97(1) 1_555 1_565 ? C17 H15A 3.05(1) 1_555 1_545 ? C12 C18 3.885(1) 1_555 4_354 ? C12 H6B 3.136(8) 1_555 3_454 ? C18 C18 3.843(2) 1_555 4_344 ? C18 C18 3.843(2) 1_555 4_354 ? C18 H18A 3.11(1) 1_555 4_354 ? C18 H15A 3.10(1) 1_555 1_545 ? C2 C2 3.820(1) 1_555 3_455 ? C2 C16 3.980(2) 1_555 3_455 ? C2 H16C 3.17(2) 1_555 3_455 ? C1 C16 3.950(2) 1_555 3_455 ? C1 H16C 3.12(2) 1_555 3_455 ? Cl1 N20 3.2372 1_555 1_565 ? Cl1 N20 3.1673 1_555 4_455 ? Cl1 C11 3.6471 1_555 3_464 ? Cl1 C3 3.7297 1_555 1_565 ? Cl1 C10 3.7482 1_555 3_464 ? Cl1 C1 3.606(1) 1_555 4_455 ? Cl1 H20A 2.285(7) 1_555 4_455 ? Cl1 H20C 2.30(1) 1_555 1_565 ? Cl1 H1B 2.897(9) 1_555 4_455 ? Cl1 H11 2.935(9) 1_555 3_464 ? O21 C3 3.225(1) 1_555 1_565 ? O21 C17 3.317(1) 1_555 1_565 ? O21 C2 3.430(1) 1_555 1_565 ? O21 H17B 2.591(9) 1_555 1_565 ? O21 H3 2.483(9) 1_555 1_565 ? C9 C9 3.837(1) 1_555 3_454 ? C5 C11 3.8063 1_555 3_454 ? C5 C10 3.836(1) 1_555 3_454 ? C6 C11 3.847(1) 1_555 3_454 ? C6 C13 3.9209 1_555 3_454 ? C6 C12 3.769(1) 1_555 3_454 ? C11 C15 3.867(1) 1_555 4_344 ? C11 H15B 3.15(1) 1_555 4_344 ? C10 C13 3.696(1) 1_555 1_545 ? C10 H5 3.111(7) 1_555 3_454 ? C10 H13 3.083(9) 1_555 1_545 ? C13 C18 3.934(1) 1_555 4_354 ? C13 H6B 3.066(9) 1_555 3_454 ? C13 H10 2.97(1) 1_555 1_565 ? C17 H15A 3.05(1) 1_555 1_545 ? C12 C18 3.885(1) 1_555 4_354 ? C12 H6B 3.136(8) 1_555 3_454 ? C18 C18 3.843(2) 1_555 4_344 ? C18 C18 3.843(2) 1_555 4_354 ? C18 H18A 3.11(1) 1_555 4_354 ? C18 H15A 3.10(1) 1_555 1_545 ? C2 C2 3.820(1) 1_555 3_455 ? C2 C16 3.980(2) 1_555 3_455 ? C2 H16C 3.17(2) 1_555 3_455 ? C1 C16 3.950(2) 1_555 3_455 ? C1 H16C 3.12(2) 1_555 3_455 ?