# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_str1509 _audit_creation_date 2013-09-05 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H44 N3 O2, Cl, 2(H2 O)' _chemical_formula_sum 'C22 H48 Cl N3 O4' _chemical_formula_weight 454.08 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C22 H44 N3 O2 Cl' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 4.83104(13) _cell_length_b 7.1526(2) _cell_length_c 38.7650(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.420(3) _cell_angle_gamma 90.00 _cell_volume 1339.47(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3427 _cell_measurement_temperature 200.00(10) _cell_measurement_theta_max 71.8150 _cell_measurement_theta_min 4.5330 _exptl_absorpt_coefficient_mu 1.491 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre ? _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary ? _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 500 _exptl_crystal_size_max 0.533 _exptl_crystal_size_mid 0.044 _exptl_crystal_size_min 0.038 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0552 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_number 7253 _diffrn_reflns_theta_full 65.49 _diffrn_reflns_theta_max 65.49 _diffrn_reflns_theta_min 4.56 _diffrn_ambient_temperature 200.00(10) _diffrn_detector_area_resol_mean 10.4051 _diffrn_measured_fraction_theta_full 0.9931 _diffrn_measured_fraction_theta_max 0.9931 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -120.00 -83.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -36.3687 -99.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega -118.00 -85.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -36.3687 -99.0000 90.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega 67.00 120.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 36.3687 178.0000 120.0000 53 #__ type_ start__ end____ width___ exp.time_ 4 omega -33.00 -7.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -70.5000 30.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega -41.00 -16.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -70.5000 37.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 117.00 169.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 111.0000 -180.0000 52 #__ type_ start__ end____ width___ exp.time_ 7 omega 26.00 81.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 -94.0000 -30.0000 55 #__ type_ start__ end____ width___ exp.time_ 8 omega 26.00 95.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 -45.0000 150.0000 69 #__ type_ start__ end____ width___ exp.time_ 9 omega 59.00 85.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 -30.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 43.00 98.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 -45.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 11 omega -128.00 3.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -36.3687 -77.0000 -60.0000 131 #__ type_ start__ end____ width___ exp.time_ 12 omega -121.00 0.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - -36.3687 -57.0000 120.0000 121 #__ type_ start__ end____ width___ exp.time_ 13 omega 20.00 178.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 15.0000 -120.0000 158 #__ type_ start__ end____ width___ exp.time_ 14 omega 73.00 178.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 61.0000 90.0000 105 #__ type_ start__ end____ width___ exp.time_ 15 omega 19.00 93.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 -94.0000 120.0000 74 #__ type_ start__ end____ width___ exp.time_ 16 omega 20.00 178.00 1.0000 9.0000 omega____ theta____ kappa____ phi______ frames - 109.6222 15.0000 30.0000 158 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0323820000 _diffrn_orient_matrix_UB_12 0.0618048000 _diffrn_orient_matrix_UB_13 -0.0378990000 _diffrn_orient_matrix_UB_21 -0.1466031000 _diffrn_orient_matrix_UB_22 -0.1857596000 _diffrn_orient_matrix_UB_23 -0.0085106000 _diffrn_orient_matrix_UB_31 -0.2813490000 _diffrn_orient_matrix_UB_32 0.0896518000 _diffrn_orient_matrix_UB_33 0.0084582000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3869 _reflns_number_total 4335 _reflns_odcompleteness_completeness 99.31 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.310 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.085 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 288 _refine_ls_number_reflns 4335 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0495 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1398P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1543 _refine_ls_wR_factor_ref 0.1916 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 H1A H -0.577(10) 0.145(7) -0.3996(13) 0.043(13) Uiso 1 1 d . . . H1B H -0.911(9) 0.172(6) -0.3943(12) 0.031(11) Uiso 1 1 d . . . C4 C -0.7745(11) 0.3444(7) -0.43292(10) 0.0456(11) Uani 1 1 d . . . H4A H -0.6434 0.2969 -0.4496 0.055 Uiso 1 1 calc R . . H4B H -0.9603 0.3281 -0.4421 0.055 Uiso 1 1 calc R . . C22 C -0.7281(15) -0.1099(8) -0.24771(13) 0.0665(16) Uani 1 1 d . . . H22A H -0.6677 -0.0389 -0.2280 0.100 Uiso 1 1 calc R . . H22B H -0.6555 -0.2346 -0.2462 0.100 Uiso 1 1 calc R . . H22C H -0.9267 -0.1147 -0.2482 0.100 Uiso 1 1 calc R . . C20 C -0.6240(10) -0.0172(7) -0.28057(10) 0.0431(9) Uani 1 1 d . . . H20 H -0.4212 -0.0209 -0.2802 0.052 Uiso 1 1 calc R . . C6 C -0.7142(7) 0.1876(5) -0.28164(8) 0.0239(7) Uani 1 1 d . . . H6 H -0.9167 0.1932 -0.2808 0.029 Uiso 1 1 calc R . . C21 C -0.7235(16) -0.1214(7) -0.31236(13) 0.0701(18) Uani 1 1 d . . . H21A H -0.6855 -0.2524 -0.3097 0.105 Uiso 1 1 calc R . . H21B H -0.6289 -0.0748 -0.3323 0.105 Uiso 1 1 calc R . . H21C H -0.9192 -0.1031 -0.3152 0.105 Uiso 1 1 calc R . . C11 C -0.8121(7) 0.3615(5) -0.09912(8) 0.0242(7) Uani 1 1 d . . . H11A H -1.0116 0.3767 -0.0991 0.029 Uiso 1 1 calc R . . H11B H -0.7731 0.2284 -0.0993 0.029 Uiso 1 1 calc R . . C15 C -0.8095(7) 0.3617(5) 0.03262(8) 0.0225(7) Uani 1 1 d . . . H15A H -1.0081 0.3816 0.0327 0.027 Uiso 1 1 calc R . . H15B H -0.7772 0.2279 0.0328 0.027 Uiso 1 1 calc R . . C3 C -0.7194(10) 0.5462(6) -0.42553(10) 0.0402(10) Uani 1 1 d . . . H3A H -0.8406 0.6256 -0.4392 0.048 Uiso 1 1 calc R . . H3B H -0.5287 0.5779 -0.4306 0.048 Uiso 1 1 calc R . . C13 C -0.8124(7) 0.3622(5) -0.03331(8) 0.0220(7) Uani 1 1 d . . . H13A H -1.0111 0.3817 -0.0333 0.026 Uiso 1 1 calc R . . H13B H -0.7797 0.2284 -0.0334 0.026 Uiso 1 1 calc R . . C14 C -0.6909(7) 0.4437(5) -0.00051(8) 0.0220(7) Uani 1 1 d . . . H14A H -0.7224 0.5777 -0.0005 0.026 Uiso 1 1 calc R . . H14B H -0.4923 0.4236 -0.0005 0.026 Uiso 1 1 calc R . . C9 C -0.8006(7) 0.3566(5) -0.16497(9) 0.0257(7) Uani 1 1 d . . . H9A H -0.7394 0.2275 -0.1654 0.031 Uiso 1 1 calc R . . H9B H -1.0014 0.3568 -0.1651 0.031 Uiso 1 1 calc R . . C17 C -0.8077(7) 0.3661(5) 0.09848(8) 0.0225(7) Uani 1 1 d . . . H17A H -1.0063 0.3861 0.0983 0.027 Uiso 1 1 calc R . . H17B H -0.7753 0.2323 0.0991 0.027 Uiso 1 1 calc R . . C16 C -0.6862(7) 0.4454(5) 0.06532(8) 0.0224(7) Uani 1 1 d . . . H16A H -0.7157 0.5796 0.0650 0.027 Uiso 1 1 calc R . . H16B H -0.4880 0.4237 0.0654 0.027 Uiso 1 1 calc R . . C7 C -0.5963(7) 0.2909(5) -0.25061(8) 0.0246(7) Uani 1 1 d . . . C2 C -0.7777(9) 0.5690(6) -0.38713(10) 0.0353(9) Uani 1 1 d . . . H2A H -0.6801 0.6760 -0.3776 0.042 Uiso 1 1 calc R . . H2B H -0.9743 0.5830 -0.3829 0.042 Uiso 1 1 calc R . . C18 C -0.6852(7) 0.4538(6) 0.13101(8) 0.0282(8) Uani 1 1 d . . . H18A H -0.7149 0.5879 0.1303 0.034 Uiso 1 1 calc R . . H18B H -0.4871 0.4319 0.1315 0.034 Uiso 1 1 calc R . . C5 C -0.7989(7) 0.3271(5) -0.33829(8) 0.0211(7) Uani 1 1 d . . . C1 C -0.6682(7) 0.3872(5) -0.37220(9) 0.0245(7) Uani 1 1 d . . . H1 H -0.4666 0.3942 -0.3695 0.029 Uiso 1 1 calc R . . C12 C -0.6941(7) 0.4457(5) -0.06625(8) 0.0226(7) Uani 1 1 d . . . H12A H -0.7299 0.5792 -0.0664 0.027 Uiso 1 1 calc R . . H12B H -0.4950 0.4283 -0.0661 0.027 Uiso 1 1 calc R . . C8 C -0.6983(8) 0.4552(6) -0.19703(9) 0.0292(8) Uani 1 1 d . . . H8A H -0.7694 0.5820 -0.1972 0.035 Uiso 1 1 calc R . . H8B H -0.4979 0.4623 -0.1960 0.035 Uiso 1 1 calc R . . C10 C -0.6974(7) 0.4480(5) -0.13197(8) 0.0239(7) Uani 1 1 d . . . H10A H -0.7467 0.5795 -0.1325 0.029 Uiso 1 1 calc R . . H10B H -0.4970 0.4400 -0.1312 0.029 Uiso 1 1 calc R . . C19 C -0.8116(9) 0.3759(7) 0.16402(9) 0.0395(10) Uani 1 1 d . . . H19A H -1.0094 0.3883 0.1629 0.059 Uiso 1 1 calc R . . H19B H -0.7415 0.4442 0.1835 0.059 Uiso 1 1 calc R . . H19C H -0.7635 0.2463 0.1664 0.059 Uiso 1 1 calc R . . N3 N -0.7799(6) 0.3634(5) -0.22874(7) 0.0263(6) Uani 1 1 d . . . H3 H -0.9532 0.3551 -0.2337 0.032 Uiso 1 1 calc R . . N1 N -0.7428(6) 0.2434(4) -0.39911(7) 0.0247(7) Uani 1 1 d . . . N2 N -0.6216(6) 0.2775(4) -0.31329(7) 0.0220(6) Uani 1 1 d . . . H2 H -0.4480 0.2992 -0.3160 0.026 Uiso 1 1 calc R . . O1 O -1.0514(5) 0.3225(5) -0.33548(6) 0.0358(6) Uani 1 1 d . . . O2 O -0.3441(5) 0.3041(6) -0.24631(7) 0.0493(9) Uani 1 1 d . . . Cl1 Cl -0.25020(17) -0.02510(14) -0.39816(2) 0.0365(3) Uani 1 1 d . . . O4 O -1.2510(6) 0.4973(5) -0.49393(8) 0.0451(7) Uani 1 1 d G . . H4C H -1.2531 0.6153 -0.4915 0.068 Uiso 1 1 d G . . H4D H -1.3879 0.4640 -0.5064 0.068 Uiso 1 1 d G . . O3 O -0.7545(6) 0.3780(5) -0.52231(8) 0.0435(7) Uani 1 1 d G . . H3C H -0.9038 0.4104 -0.5124 0.065 Uiso 1 1 d G . . H3D H -0.7678 0.3990 -0.5438 0.065 Uiso 1 1 d G . . 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 C4 0.070(3) 0.048(2) 0.0196(17) 0.0026(18) -0.0049(19) -0.007(2) C22 0.116(5) 0.049(3) 0.035(2) 0.017(2) 0.006(3) -0.001(3) C20 0.060(3) 0.043(2) 0.0264(18) 0.0052(19) 0.0061(17) 0.002(2) C6 0.0163(16) 0.0417(18) 0.0138(14) 0.0004(14) 0.0062(12) -0.0046(14) C21 0.135(6) 0.039(2) 0.037(2) -0.007(2) 0.004(3) -0.006(3) C11 0.0238(17) 0.0276(17) 0.0211(16) 0.0014(13) 0.0019(13) -0.0016(14) C15 0.0186(16) 0.0292(18) 0.0196(15) 0.0026(14) 0.0024(13) 0.0010(13) C3 0.056(3) 0.039(2) 0.0259(18) 0.0045(16) 0.0025(18) -0.0013(19) C13 0.0228(16) 0.0271(17) 0.0161(15) -0.0004(13) 0.0039(13) 0.0010(13) C14 0.0192(16) 0.0260(17) 0.0207(16) 0.0039(13) 0.0035(13) -0.0012(13) C9 0.0269(18) 0.0285(17) 0.0218(16) 0.0004(14) 0.0014(13) -0.0052(14) C17 0.0204(16) 0.0274(17) 0.0197(16) 0.0000(13) 0.0026(13) -0.0005(14) C16 0.0211(17) 0.0253(17) 0.0208(16) 0.0018(13) 0.0020(13) -0.0002(13) C7 0.0138(16) 0.0429(19) 0.0170(15) 0.0003(13) 0.0048(12) -0.0013(14) C2 0.048(2) 0.0303(19) 0.0281(18) 0.0000(16) 0.0093(17) 0.0012(17) C18 0.0254(17) 0.038(2) 0.0213(16) -0.0018(15) 0.0006(13) 0.0010(15) C5 0.0161(15) 0.0315(17) 0.0158(14) -0.0035(12) 0.0070(12) -0.0019(13) C1 0.0178(16) 0.0346(18) 0.0211(16) -0.0011(14) 0.0051(13) -0.0043(14) C12 0.0231(17) 0.0268(18) 0.0180(15) 0.0027(13) 0.0029(12) 0.0000(13) C8 0.0288(18) 0.038(2) 0.0208(15) -0.0026(15) 0.0060(13) -0.0109(17) C10 0.0251(17) 0.0267(17) 0.0199(16) 0.0025(13) 0.0032(12) -0.0024(14) C19 0.043(2) 0.055(3) 0.0210(17) 0.0032(17) 0.0010(16) 0.005(2) N3 0.0141(13) 0.0463(18) 0.0184(13) -0.0021(13) 0.0026(11) -0.0027(12) N1 0.0240(16) 0.0296(16) 0.0205(14) 0.0004(11) 0.0080(12) 0.0003(12) N2 0.0121(13) 0.0384(15) 0.0156(12) 0.0033(11) 0.0049(10) -0.0012(11) O1 0.0149(12) 0.0667(18) 0.0258(12) 0.0078(12) 0.0047(10) -0.0012(12) O2 0.0130(13) 0.097(3) 0.0377(15) -0.0175(16) 0.0001(11) -0.0024(15) Cl1 0.0254(4) 0.0344(4) 0.0499(5) -0.0047(4) 0.0063(4) 0.0008(4) O4 0.0376(15) 0.0479(17) 0.0497(16) -0.0044(14) 0.0001(13) -0.0010(14) O3 0.0335(16) 0.0500(16) 0.0470(17) 0.0007(15) 0.0041(13) 0.0039(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 C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C3 1.495(7) . ? C4 N1 1.503(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22 C20 1.525(6) . ? C20 H20 0.9800 . ? C20 C6 1.529(6) . ? C20 C21 1.515(7) . ? C6 H6 0.9800 . ? C6 C7 1.519(5) . ? C6 N2 1.458(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.517(4) . ? C11 C10 1.524(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C14 1.527(4) . ? C15 C16 1.519(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C2 1.526(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.514(4) . ? C13 C12 1.524(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C8 1.515(5) . ? C9 C10 1.518(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C16 1.526(4) . ? C17 C18 1.524(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C7 N3 1.336(5) . ? C7 O2 1.232(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C1 1.517(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 C19 1.527(5) . ? C5 C1 1.524(4) . ? C5 N2 1.336(4) . ? C5 O1 1.226(4) . ? C1 H1 0.9800 . ? C1 N1 1.507(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 N3 1.446(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N3 H3 0.8600 . ? N1 H1A 1.07(5) . ? N1 H1B 0.98(5) . ? N2 H2 0.8600 . ? O4 H4C 0.8501 . ? O4 H4D 0.8493 . ? O3 H3C 0.8506 . ? O3 H3D 0.8496 . ? 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 H4A C4 H4B 108.7 . . ? C3 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? C3 C4 N1 106.3(3) . . ? N1 C4 H4A 110.5 . . ? N1 C4 H4B 110.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? C22 C20 H20 108.1 . . ? C22 C20 C6 110.1(4) . . ? C6 C20 H20 108.1 . . ? C21 C20 C22 111.1(5) . . ? C21 C20 H20 108.1 . . ? C21 C20 C6 111.2(4) . . ? C20 C6 H6 108.8 . . ? C7 C6 C20 109.9(3) . . ? C7 C6 H6 108.8 . . ? N2 C6 C20 110.9(3) . . ? N2 C6 H6 108.8 . . ? N2 C6 C7 109.7(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? H11A C11 H11B 107.7 . . ? C12 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C12 C11 C10 113.8(3) . . ? C10 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? H15A C15 H15B 107.7 . . ? C14 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C16 C15 C14 113.8(3) . . ? C4 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C4 C3 C2 104.8(3) . . ? H3A C3 H3B 108.9 . . ? C2 C3 H3A 110.8 . . ? C2 C3 H3B 110.8 . . ? H13A C13 H13B 107.6 . . ? C14 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C14 C13 C12 114.0(3) . . ? C12 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C15 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 C15 114.4(3) . . ? C13 C14 H14A 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? H9A C9 H9B 107.8 . . ? C8 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C8 C9 C10 112.6(3) . . ? C10 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? H17A C17 H17B 107.7 . . ? C16 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C18 C17 C16 113.3(3) . . ? C15 C16 C17 113.9(3) . . ? C15 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? N3 C7 C6 116.4(3) . . ? O2 C7 C6 120.6(3) . . ? O2 C7 N3 123.0(3) . . ? C3 C2 H2A 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C1 C2 C3 102.4(3) . . ? C1 C2 H2A 111.3 . . ? C1 C2 H2B 111.3 . . ? C17 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C17 C18 C19 112.8(3) . . ? H18A C18 H18B 107.8 . . ? C19 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? N2 C5 C1 115.6(3) . . ? O1 C5 C1 120.2(3) . . ? O1 C5 N2 124.1(3) . . ? C2 C1 C5 115.2(3) . . ? C2 C1 H1 109.9 . . ? C5 C1 H1 109.9 . . ? N1 C1 C2 103.9(3) . . ? N1 C1 C5 107.8(3) . . ? N1 C1 H1 109.9 . . ? C11 C12 C13 114.0(3) . . ? C11 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C9 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N3 C8 C9 113.4(3) . . ? N3 C8 H8A 108.9 . . ? N3 C8 H8B 108.9 . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 C11 114.2(3) . . ? C9 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 N3 C8 122.5(3) . . ? C7 N3 H3 118.7 . . ? C8 N3 H3 118.7 . . ? H1A N1 H1B 106(4) . . ? C4 N1 H1A 112(3) . . ? C4 N1 H1B 110(3) . . ? C4 N1 C1 107.3(3) . . ? C1 N1 H1A 107(3) . . ? C1 N1 H1B 115(3) . . ? C6 N2 H2 119.1 . . ? C5 N2 C6 121.9(3) . . ? C5 N2 H2 119.1 . . ? H4C O4 H4D 109.4 . . ? H3C O3 H3D 109.6 . . ? _database_code_depnum_ccdc_archive 'CCDC 951964'