# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/321 # CIF # Prepared by Kevin J. McCullough 5th February 1999 data_global #======================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr K. J. McCullough Department of Chemistry Heriot-Watt University Riccarton Edinburgh EH14 4AS ; _publ_contact_author_phone '0131 449-5111 ext 4120' _publ_contact_author_fax '0131 451 3180' _publ_contact_author_email k.j.mccullough@hw.ac.uk _publ_requested_journal 'J. Chem. Soc. Perkin Transactions' _publ_requested_coeditor_name ? _publ_contact_letter ; ;#============================================================ # 3. TITLE AND AUTHOR LIST _publ_section_title ; Preparation of 1,2,4-triazoloquinazonium betaines and nolecular rearrangements of putative 1,2,4-triazolo[4,3a][1,3,5]triazinium betaines ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Crabb, Derek L.' ; Department of Chemistry Heriot-Watt University Riccarton Edinburgh EH14 4AS ; 'McCullough, Kevin J.' ; Department of Chemistry Heriot-Watt University Riccarton Edinburgh EH14 4AS ; 'Preston, Peter N.' ; Department of Chemistry Heriot-Watt University Riccarton Edinburgh EH14 4AS ; 'Rosair, Georgina M.' ; Department of Chemistry Heriot-Watt University Riccarton Edinburgh EH14 4AS ; 'Bishop, Brian C.' ; Merck, Sharp and Dohme Laboratories Hertford Road Hoddesdon Hertfordshire EN11 9BU ; 'Wright, Stanley H.B.' ; Merck, Sharp and Dohme Laboratories Hertford Road Hoddesdon Hertfordshire EN11 9BU ; 'Clegg, William' ; Department of Chemistry University of Newcastle Newcastle-upon-Tyne UK, NE1 7RU ; 'Coles, Simon.' ; CCLR, Daresbury Laboratory Warrington UK WA4 4AD ; data_compound8a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H15 N5' _chemical_formula_weight 289.34 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7511(7) _cell_length_b 7.3223(12) _cell_length_c 20.122(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.377(12) _cell_angle_gamma 90.00 _cell_volume 1408.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method ? _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5617 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.85 _reflns_number_total 2100 _reflns_number_observed 1661 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2097 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_obs 0.0437 _refine_ls_wR_factor_all 0.1333 _refine_ls_wR_factor_obs 0.1031 _refine_ls_goodness_of_fit_all 0.976 _refine_ls_goodness_of_fit_obs 1.077 _refine_ls_restrained_S_all 1.223 _refine_ls_restrained_S_obs 1.077 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.3161(2) 0.2277(2) 0.87847(7) 0.0237(4) Uani 1 d . . N2 N 0.42370(14) 0.2886(2) 0.99601(7) 0.0201(4) Uani 1 d . . N3 N 0.20715(15) 0.3630(2) 0.96291(7) 0.0238(4) Uani 1 d . . N4 N 0.2378(2) 0.4081(2) 1.03105(8) 0.0247(4) Uani 1 d . . N5 N 0.4604(2) 0.3729(2) 1.11154(8) 0.0243(4) Uani 1 d . . C1 C 0.4343(2) 0.1542(2) 0.86944(9) 0.0220(4) Uani 1 d . . C2 C 0.3158(2) 0.2916(2) 0.94176(9) 0.0210(4) Uani 1 d . . C3 C 0.5532(2) 0.2152(2) 0.98837(9) 0.0199(4) Uani 1 d . . C4 C 0.6695(2) 0.2083(2) 1.04111(9) 0.0229(4) Uani 1 d . . H4 H 0.6653(2) 0.2550(2) 1.08471(9) 0.028 Uiso 1 calc R . C5 C 0.7917(2) 0.1314(2) 1.02825(10) 0.0263(5) Uani 1 d . . H5 H 0.8720(2) 0.1261(2) 1.06363(10) 0.032 Uiso 1 calc R . C6 C 0.7991(2) 0.0621(2) 0.96482(9) 0.0267(5) Uani 1 d . . H6 H 0.8839(2) 0.0098(2) 0.95728(9) 0.032 Uiso 1 calc R . C7 C 0.6835(2) 0.0690(2) 0.91271(10) 0.0251(5) Uani 1 d . . H7 H 0.6890(2) 0.0210(2) 0.86945(10) 0.030 Uiso 1 calc R . C8 C 0.5579(2) 0.1466(2) 0.92329(9) 0.0208(4) Uani 1 d . . C9 C 0.3737(2) 0.3625(2) 1.05269(9) 0.0208(4) Uani 1 d . . C10 C 0.2975(2) 0.5377(2) 1.17387(10) 0.0247(5) Uani 1 d . . H10 H 0.2243(2) 0.5453(2) 1.13509(10) 0.030 Uiso 1 calc R . C11 C 0.2802(2) 0.6154(2) 1.23492(10) 0.0284(5) Uani 1 d . . H11 H 0.1953(2) 0.6770(2) 1.23688(10) 0.034 Uiso 1 calc R . C12 C 0.3835(2) 0.6048(2) 1.29266(10) 0.0302(5) Uani 1 d . . H12 H 0.3706(2) 0.6591(2) 1.33385(10) 0.036 Uiso 1 calc R . C13 C 0.5069(2) 0.5132(3) 1.28930(10) 0.0305(5) Uani 1 d . . H13 H 0.5785(2) 0.5026(3) 1.32865(10) 0.037 Uiso 1 calc R . C14 C 0.5254(2) 0.4374(2) 1.22874(9) 0.0271(5) Uani 1 d . . H14 H 0.6106(2) 0.3759(2) 1.22735(9) 0.032 Uiso 1 calc R . C15 C 0.4229(2) 0.4483(2) 1.16941(9) 0.0218(4) Uani 1 d . . C16 C 0.0694(2) 0.3981(3) 0.92252(10) 0.0317(5) Uani 1 d G . H161 H 0.0650(16) 0.3527(15) 0.8779(3) 0.038 Uiso 1 d G . H162 H 0.0510(15) 0.5256(4) 0.9206(7) 0.038 Uiso 1 d G . H163 H 0.0015(12) 0.3377(15) 0.9426(7) 0.038 Uiso 1 d G . C17 C 0.4370(2) 0.0737(3) 0.80176(10) 0.0298(5) Uani 1 d G . H171 H 0.4614(12) -0.0513(5) 0.8088(7) 0.036 Uiso 1 d G . H172 H 0.3478(7) 0.0834(17) 0.7724(6) 0.036 Uiso 1 d G . H173 H 0.5056(10) 0.1320(16) 0.7810(7) 0.036 Uiso 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 N1 0.0229(9) 0.0238(9) 0.0247(10) 0.0015(6) 0.0056(7) -0.0015(6) N2 0.0167(8) 0.0224(9) 0.0211(9) 0.0016(6) 0.0040(7) -0.0011(6) N3 0.0184(9) 0.0279(9) 0.0245(10) -0.0010(6) 0.0028(7) 0.0001(6) N4 0.0215(9) 0.0280(9) 0.0243(10) -0.0002(7) 0.0038(7) -0.0004(6) N5 0.0225(9) 0.0270(9) 0.0233(10) 0.0002(6) 0.0044(7) 0.0002(6) C1 0.0234(11) 0.0197(10) 0.0236(11) 0.0037(7) 0.0062(8) -0.0042(8) C2 0.0185(10) 0.0208(10) 0.0237(11) 0.0020(7) 0.0041(8) -0.0022(7) C3 0.0190(10) 0.0179(10) 0.0243(11) 0.0052(7) 0.0081(8) -0.0015(7) C4 0.0222(10) 0.0247(11) 0.0218(11) 0.0031(7) 0.0042(8) -0.0019(8) C5 0.0197(11) 0.0312(11) 0.0271(12) 0.0080(8) 0.0024(9) 0.0012(8) C6 0.0208(11) 0.0289(11) 0.0320(12) 0.0071(8) 0.0092(9) 0.0047(8) C7 0.0258(11) 0.0244(11) 0.0269(11) 0.0014(8) 0.0101(9) -0.0006(8) C8 0.0216(10) 0.0171(10) 0.0252(11) 0.0038(7) 0.0081(8) -0.0035(7) C9 0.0201(10) 0.0186(10) 0.0246(11) 0.0010(7) 0.0063(9) -0.0011(7) C10 0.0238(11) 0.0255(11) 0.0252(11) 0.0035(8) 0.0057(9) -0.0013(8) C11 0.0272(12) 0.0294(12) 0.0314(13) 0.0016(8) 0.0131(9) 0.0010(8) C12 0.0391(13) 0.0312(12) 0.0236(12) -0.0020(8) 0.0142(10) -0.0041(9) C13 0.0338(12) 0.0333(12) 0.0226(12) 0.0008(8) 0.0013(9) -0.0002(9) C14 0.0257(11) 0.0266(11) 0.0284(12) -0.0014(8) 0.0041(9) 0.0034(8) C15 0.0213(10) 0.0197(10) 0.0248(11) 0.0011(7) 0.0057(8) -0.0028(7) C16 0.0206(11) 0.0376(13) 0.0345(13) -0.0041(9) -0.0003(9) 0.0018(8) C17 0.0269(11) 0.0355(12) 0.0269(12) -0.0017(8) 0.0052(9) 0.0012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.316(2) . ? N1 C2 1.357(2) . ? N2 C2 1.358(2) . ? N2 C3 1.408(2) . ? N2 C9 1.432(2) . ? N3 C2 1.325(2) . ? N3 N4 1.384(2) . ? N3 C16 1.449(2) . ? N4 C9 1.353(2) . ? N5 C9 1.314(2) . ? N5 C15 1.401(2) . ? C1 C8 1.454(2) . ? C1 C17 1.489(3) . ? C3 C4 1.393(3) . ? C3 C8 1.412(3) . ? C4 C5 1.387(2) . ? C5 C6 1.389(3) . ? C6 C7 1.381(3) . ? C7 C8 1.405(2) . ? C10 C11 1.394(3) . ? C10 C15 1.405(3) . ? C11 C12 1.382(3) . ? C12 C13 1.390(3) . ? C13 C14 1.383(3) . ? C14 C15 1.400(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 115.7(2) . . ? C2 N2 C3 119.16(15) . . ? C2 N2 C9 107.62(14) . . ? C3 N2 C9 133.19(15) . . ? C2 N3 N4 112.47(15) . . ? C2 N3 C16 127.0(2) . . ? N4 N3 C16 120.5(2) . . ? C9 N4 N3 105.44(14) . . ? C9 N5 C15 123.0(2) . . ? N1 C1 C8 122.1(2) . . ? N1 C1 C17 117.5(2) . . ? C8 C1 C17 120.3(2) . . ? N3 C2 N1 126.0(2) . . ? N3 C2 N2 106.9(2) . . ? N1 C2 N2 127.1(2) . . ? C4 C3 N2 122.9(2) . . ? C4 C3 C8 121.5(2) . . ? N2 C3 C8 115.5(2) . . ? C5 C4 C3 118.2(2) . . ? C4 C5 C6 121.5(2) . . ? C7 C6 C5 120.1(2) . . ? C6 C7 C8 120.4(2) . . ? C7 C8 C3 118.3(2) . . ? C7 C8 C1 121.5(2) . . ? C3 C8 C1 120.3(2) . . ? N5 C9 N4 133.7(2) . . ? N5 C9 N2 118.7(2) . . ? N4 C9 N2 107.61(15) . . ? C11 C10 C15 120.3(2) . . ? C12 C11 C10 121.5(2) . . ? C11 C12 C13 118.7(2) . . ? C14 C13 C12 120.1(2) . . ? C13 C14 C15 122.2(2) . . ? C14 C15 N5 115.3(2) . . ? C14 C15 C10 117.1(2) . . ? N5 C15 C10 127.6(2) . . ? _refine_diff_density_max 0.247 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.053 #===END data_compound17a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H25 N11' _chemical_formula_weight 407.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.023(2) _cell_length_b 11.419(2) _cell_length_c 11.582(2) _cell_angle_alpha 91.53(3) _cell_angle_beta 97.30(3) _cell_angle_gamma 105.76(3) _cell_volume 1010.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method ? _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3383 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0763 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 24.94 _reflns_number_total 2628 _reflns_number_observed 1941 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2626 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_obs 0.0496 _refine_ls_wR_factor_all 0.1353 _refine_ls_wR_factor_obs 0.1227 _refine_ls_goodness_of_fit_all 0.942 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 1.010 _refine_ls_restrained_S_obs 1.088 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.5391(3) 1.0759(2) 0.8273(2) 0.0255(6) Uani 1 d . . C1 C 0.4745(4) 0.9565(2) 0.7937(2) 0.0224(7) Uani 1 d . . N2 N 0.2882(3) 1.0551(2) 0.9245(2) 0.0296(6) Uani 1 d . . C2 C 0.4402(4) 1.1205(3) 0.8914(2) 0.0252(7) Uani 1 d . . N3 N 0.3198(3) 0.8832(2) 0.8171(2) 0.0248(6) Uani 1 d . . C3 C 0.2361(4) 0.9379(3) 0.8849(3) 0.0282(7) Uani 1 d . . N4 N 0.5704(3) 0.9070(2) 0.7289(2) 0.0268(6) Uani 1 d . . C4 C 0.4993(4) 1.2531(3) 0.9267(3) 0.0316(8) Uani 1 d G . H4A H 0.6259(6) 1.2851(22) 0.9276(21) 0.047 Uiso 0.89(3) d PG . H4B H 0.4703(31) 1.2632(24) 1.0054(8) 0.047 Uiso 0.89(3) d PG . H4C H 0.4386(28) 1.2978(21) 0.8730(17) 0.047 Uiso 0.89(3) d PG . H4D H 0.3973(21) 1.2789(23) 0.9430(21) 0.047 Uiso 0.11(3) d PG . H4E H 0.5529(29) 1.3008(21) 0.8652(15) 0.047 Uiso 0.11(3) d PG . H4F H 0.5846(24) 1.2663(24) 0.9977(12) 0.047 Uiso 0.11(3) d PG . N5 N 0.5349(3) 0.7760(2) 0.7238(2) 0.0262(6) Uani 1 d . . C5 C 0.0715(5) 0.8576(3) 0.9216(3) 0.0500(10) Uani 1 d G . H5A H 0.0158(38) 0.9070(25) 0.9659(23) 0.075 Uiso 0.88(4) d PG . H5B H 0.1027(41) 0.7962(22) 0.9709(22) 0.075 Uiso 0.88(4) d PG . H5C H -0.0098(32) 0.8169(27) 0.8528(16) 0.075 Uiso 0.88(4) d PG . H5D H 0.0566(42) 0.7731(11) 0.8938(26) 0.075 Uiso 0.12(4) d PG . H5E H -0.0302(27) 0.8839(28) 0.8889(25) 0.075 Uiso 0.12(4) d PG . H5F H 0.0823(41) 0.8631(30) 1.0069(3) 0.075 Uiso 0.12(4) d PG . C9 C 0.4683(3) 0.5137(2) 0.6713(2) 0.0182(6) Uani 1 d . . C6 C 0.7505(4) 0.9745(3) 0.7160(3) 0.0398(9) Uani 1 d G . H6A H 0.8014(32) 0.9262(20) 0.6655(15) 0.060 Uiso 1 d G . H6B H 0.8175(29) 0.9872(21) 0.7954(8) 0.060 Uiso 1 d G . H6C H 0.7562(35) 1.0545(11) 0.6833(19) 0.060 Uiso 1 d G . N7 N 0.3966(3) 0.3969(2) 0.6484(2) 0.0196(6) Uani 1 d . . C7 C 0.4058(4) 0.7886(3) 0.5176(2) 0.0237(7) Uani 1 d G . H7A H 0.4809(26) 0.8726(8) 0.5226(22) 0.036 Uiso 0.85(3) d PG . H7B H 0.2842(11) 0.7893(22) 0.5189(21) 0.036 Uiso 0.85(3) d PG . H7C H 0.4150(32) 0.7465(20) 0.4449(12) 0.036 Uiso 0.85(3) d PG . H7D H 0.3058(20) 0.7330(18) 0.4683(18) 0.036 Uiso 0.15(3) d PG . H7E H 0.5025(21) 0.8163(21) 0.4720(18) 0.036 Uiso 0.15(3) d PG . H7F H 0.3718(31) 0.8591(14) 0.5461(20) 0.036 Uiso 0.15(3) d PG . N8 N 0.1709(3) 0.2344(2) 0.5481(2) 0.0199(6) Uani 1 d . . C8 C 0.4619(4) 0.7261(2) 0.6224(2) 0.0207(7) Uani 1 d . . N9 N 0.0344(3) 0.2121(2) 0.4555(2) 0.0217(6) Uani 1 d . . N6 N 0.4222(3) 0.6002(2) 0.6034(2) 0.0194(6) Uani 1 d . . H6 H 0.3324(30) 0.5662(12) 0.5428(20) 0.029 Uiso 1 d R . N10 N 0.1894(3) 0.4134(2) 0.4758(2) 0.0192(5) Uani 1 d . . C10 C 0.6111(4) 0.5527(3) 0.7737(2) 0.0237(7) Uani 1 d G . H10A H 0.6479(25) 0.4796(11) 0.7930(17) 0.036 Uiso 1.00(3) d PG . H10B H 0.5691(27) 0.5828(15) 0.8412(12) 0.036 Uiso 1.00(3) d PG . H10C H 0.7106(18) 0.6158(11) 0.7529(19) 0.036 Uiso 1.00(3) d PG . H10D H 0.6371(26) 0.6392(5) 0.7984(17) 0.036 Uiso 0.00(3) d PG . H10E H 0.7159(17) 0.5360(16) 0.7502(19) 0.036 Uiso 0.00(3) d PG . H10F H 0.5745(27) 0.5030(14) 0.8385(12) 0.036 Uiso 0.00(3) d PG . N11 N -0.0584(3) 0.3404(2) 0.3225(2) 0.0220(6) Uani 1 d . . H11 H -0.1321(25) 0.2658(25) 0.2813(14) 0.033 Uiso 1 d R . C11 C 0.2579(3) 0.3534(2) 0.5598(2) 0.0171(6) Uani 1 d . . C12 C 0.1900(4) 0.1376(3) 0.6229(3) 0.0275(7) Uani 1 d G . H12A H 0.3109(10) 0.1586(22) 0.6621(18) 0.041 Uiso 0.91(3) d PG . H12B H 0.1640(29) 0.0604(12) 0.5762(18) 0.041 Uiso 0.91(3) d PG . H12C H 0.1100(23) 0.1294(22) 0.6813(15) 0.041 Uiso 0.91(3) d PG . H12D H 0.0791(16) 0.0736(16) 0.6176(21) 0.041 Uiso 0.09(3) d PG . H12E H 0.2259(29) 0.1718(21) 0.7036(8) 0.041 Uiso 0.09(3) d PG . H12F H 0.2799(21) 0.1028(20) 0.5984(19) 0.041 Uiso 0.09(3) d PG . C13 C 0.0538(3) 0.3236(2) 0.4159(2) 0.0192(7) Uani 1 d . . C14 C -0.1795(4) 0.4351(3) 0.1635(2) 0.0272(7) Uani 1 d . . H14 H -0.2607(26) 0.3488(27) 0.1335(10) 0.041 Uiso 1 calc R . C15 C -0.1921(4) 0.5350(3) 0.1026(3) 0.0321(8) Uani 1 d . . H15 H -0.2769(31) 0.5245(5) 0.0328(25) 0.048 Uiso 1 calc R . C16 C -0.0851(4) 0.6502(3) 0.1399(3) 0.0315(8) Uani 1 d . . H16 H -0.0949(5) 0.7242(24) 0.0952(15) 0.047 Uiso 1 calc R . C17 C 0.0360(4) 0.6626(3) 0.2397(3) 0.0335(8) Uani 1 d . . H17 H 0.1143(28) 0.7439(29) 0.2665(10) 0.050 Uiso 1 calc R . C18 C 0.0489(4) 0.5631(3) 0.3020(3) 0.0288(8) Uani 1 d . . H18 H 0.1265(31) 0.5731(5) 0.3657(25) 0.043 Uiso 1 calc R . C19 C -0.0593(3) 0.4475(2) 0.2651(2) 0.0195(7) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.029(2) 0.0184(14) 0.0262(14) -0.0010(11) -0.0048(11) 0.0067(11) C1 0.028(2) 0.017(2) 0.020(2) 0.0008(12) -0.0030(13) 0.0051(14) N2 0.043(2) 0.0206(15) 0.0269(15) 0.0043(12) 0.0060(12) 0.0113(12) C2 0.036(2) 0.021(2) 0.017(2) 0.0014(13) -0.0072(13) 0.0117(15) N3 0.027(2) 0.0206(14) 0.0261(14) 0.0017(11) 0.0028(11) 0.0051(11) C3 0.035(2) 0.025(2) 0.026(2) 0.0034(14) 0.0055(14) 0.0109(15) N4 0.026(2) 0.0158(14) 0.036(2) -0.0024(11) 0.0071(12) 0.0011(11) C4 0.037(2) 0.023(2) 0.032(2) -0.0028(14) -0.0081(14) 0.0100(15) N5 0.030(2) 0.0173(14) 0.029(2) -0.0020(11) 0.0037(12) 0.0046(11) C5 0.058(3) 0.033(2) 0.069(3) 0.007(2) 0.037(2) 0.015(2) C9 0.016(2) 0.020(2) 0.020(2) 0.0005(12) 0.0057(12) 0.0052(13) C6 0.031(2) 0.026(2) 0.061(2) -0.004(2) 0.013(2) 0.004(2) N7 0.0185(14) 0.0198(14) 0.0202(13) 0.0010(10) 0.0030(10) 0.0049(10) C7 0.024(2) 0.018(2) 0.028(2) 0.0025(13) 0.0041(13) 0.0035(13) N8 0.0196(15) 0.0181(14) 0.0214(13) 0.0038(10) -0.0009(10) 0.0054(10) C8 0.018(2) 0.018(2) 0.026(2) -0.0011(13) 0.0070(13) 0.0029(12) N9 0.0191(14) 0.0196(14) 0.0245(14) 0.0009(11) -0.0013(10) 0.0041(10) N6 0.0166(14) 0.0178(13) 0.0222(13) -0.0011(11) -0.0007(10) 0.0040(10) N10 0.0186(14) 0.0195(13) 0.0190(13) 0.0012(10) 0.0029(10) 0.0044(10) C10 0.023(2) 0.026(2) 0.024(2) -0.0001(13) 0.0017(13) 0.0089(13) N11 0.0228(15) 0.0183(13) 0.0228(14) 0.0017(11) -0.0030(10) 0.0049(11) C11 0.016(2) 0.018(2) 0.019(2) 0.0014(12) 0.0057(12) 0.0057(12) C12 0.027(2) 0.024(2) 0.031(2) 0.0057(14) -0.0006(14) 0.0071(14) C13 0.014(2) 0.022(2) 0.022(2) 0.0020(13) 0.0045(13) 0.0056(13) C14 0.030(2) 0.027(2) 0.024(2) 0.0015(14) 0.0012(14) 0.0088(14) C15 0.040(2) 0.037(2) 0.022(2) 0.0060(15) 0.0021(14) 0.016(2) C16 0.036(2) 0.029(2) 0.035(2) 0.013(2) 0.013(2) 0.012(2) C17 0.027(2) 0.022(2) 0.051(2) 0.009(2) 0.007(2) 0.0045(14) C18 0.023(2) 0.025(2) 0.036(2) 0.0020(14) -0.0032(14) 0.0062(14) C19 0.019(2) 0.021(2) 0.021(2) 0.0018(13) 0.0068(12) 0.0072(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.337(3) . ? N1 C1 1.348(3) . ? C1 N4 1.355(3) . ? C1 N3 1.360(4) . ? N2 C3 1.338(4) . ? N2 C2 1.353(4) . ? C2 C4 1.487(4) . ? N3 C3 1.339(3) . ? C3 C5 1.507(4) . ? N4 N5 1.444(3) . ? N4 C6 1.469(4) . ? N5 C8 1.286(4) . ? C9 N7 1.306(3) . ? C9 N6 1.378(3) . ? C9 C10 1.505(4) . ? N7 C11 1.386(4) . ? C7 C8 1.505(4) . ? N8 C11 1.343(3) . ? N8 N9 1.397(3) . ? N8 C12 1.450(3) . ? C8 N6 1.390(3) . ? N9 C13 1.340(3) . ? N10 C11 1.350(3) . ? N10 C13 1.372(4) . ? N11 C13 1.370(3) . ? N11 C19 1.408(3) . ? C14 C15 1.377(4) . ? C14 C19 1.401(4) . ? C15 C16 1.384(4) . ? C16 C17 1.390(4) . ? C17 C18 1.382(4) . ? C18 C19 1.390(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 114.7(3) . . ? N1 C1 N4 116.9(3) . . ? N1 C1 N3 125.3(3) . . ? N4 C1 N3 117.8(2) . . ? C3 N2 C2 114.8(2) . . ? N1 C2 N2 125.2(3) . . ? N1 C2 C4 117.6(3) . . ? N2 C2 C4 117.2(3) . . ? C3 N3 C1 114.1(2) . . ? N2 C3 N3 125.9(3) . . ? N2 C3 C5 118.1(3) . . ? N3 C3 C5 116.0(3) . . ? C1 N4 N5 116.9(2) . . ? C1 N4 C6 120.6(2) . . ? N5 N4 C6 115.4(2) . . ? C8 N5 N4 112.5(2) . . ? N7 C9 N6 122.5(3) . . ? N7 C9 C10 117.6(2) . . ? N6 C9 C10 119.8(2) . . ? C9 N7 C11 121.3(2) . . ? C11 N8 N9 110.2(2) . . ? C11 N8 C12 129.2(2) . . ? N9 N8 C12 120.2(2) . . ? N5 C8 N6 119.2(3) . . ? N5 C8 C7 127.3(3) . . ? N6 C8 C7 113.4(2) . . ? C13 N9 N8 101.7(2) . . ? C9 N6 C8 130.9(3) . . ? C11 N10 C13 103.2(2) . . ? C13 N11 C19 129.3(2) . . ? N8 C11 N10 109.9(2) . . ? N8 C11 N7 120.2(2) . . ? N10 C11 N7 129.9(2) . . ? N9 C13 N11 119.8(3) . . ? N9 C13 N10 115.0(2) . . ? N11 C13 N10 125.2(2) . . ? C15 C14 C19 121.0(3) . . ? C14 C15 C16 120.7(3) . . ? C15 C16 C17 118.5(3) . . ? C18 C17 C16 121.3(3) . . ? C17 C18 C19 120.3(3) . . ? C18 C19 C14 118.3(3) . . ? C18 C19 N11 125.0(3) . . ? C14 C19 N11 116.8(3) . . ? _refine_diff_density_max 0.367 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.066 #===END data_compound18 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H28 Cl3 N12' _chemical_formula_weight 626.96 _chemical_melting_point ? _chemical_compound_source ? 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' _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 9.576(7) _cell_length_b 12.716(9) _cell_length_c 13.076(9) _cell_angle_alpha 78.89(2) _cell_angle_beta 76.29(2) _cell_angle_gamma 78.57(2) _cell_volume 1498.3(18) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 70 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.030 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method ? _exptl_crystal_F_000 650 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.68790 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'silicon 1 1 1' _diffrn_measurement_device 'SIEMENS SMART' _diffrn_measurement_method '\w rotation frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8345 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.98 _reflns_number_total 6098 _reflns_number_observed 5189 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SIEMENS SMART' _computing_cell_refinement 'SIEMENS SMART' _computing_data_reduction 'SIEMENS SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1547P)^2^+1.1939P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6095 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_obs 0.0735 _refine_ls_wR_factor_all 0.2262 _refine_ls_wR_factor_obs 0.2136 _refine_ls_goodness_of_fit_all 0.999 _refine_ls_goodness_of_fit_obs 1.043 _refine_ls_restrained_S_all 1.017 _refine_ls_restrained_S_obs 1.043 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.1651(2) 0.4669(2) 0.2734(2) 0.0238(4) Uani 1 d . . N2 N 0.0988(2) 0.3547(2) 0.4360(2) 0.0299(5) Uani 1 d . . N3 N 0.0719(2) 0.5366(2) 0.1117(2) 0.0246(4) Uani 1 d . . N4 N 0.1161(2) 0.6542(2) 0.1982(2) 0.0265(5) Uani 1 d . . N5 N 0.0640(2) 0.7167(2) 0.1129(2) 0.0280(5) Uani 1 d . . N6 N -0.0173(3) 0.6618(2) -0.0256(2) 0.0290(5) Uani 1 d . . H6A H -0.0181(3) 0.6047(2) -0.0541(2) 0.035 Uiso 1 calc R . N7 N 0.3997(2) 0.4667(2) 0.1776(2) 0.0250(4) Uani 1 d . . N8 N 0.6396(2) 0.4737(2) 0.1902(2) 0.0260(4) Uani 1 d . . N9 N 0.5310(2) 0.5403(2) 0.3575(2) 0.0240(4) Uani 1 d . . N10 N 0.5699(2) 0.6600(2) 0.2132(2) 0.0276(5) Uani 1 d . . N11 N 0.5097(2) 0.7210(2) 0.2947(2) 0.0277(5) Uani 1 d . . N12 N 0.4257(2) 0.6617(2) 0.4800(2) 0.0265(5) Uani 1 d . . H12A H 0.4477(2) 0.6090(2) 0.5309(2) 0.032 Uiso 1 calc R . C1 C 0.3143(3) 0.4243(2) 0.2603(2) 0.0233(5) Uani 1 d . . C2 C 0.3491(3) 0.3385(2) 0.3428(2) 0.0267(5) Uani 1 d . . H2A H 0.4471(3) 0.3035(2) 0.3394(2) 0.032 Uiso 1 calc R . C3 C 0.0640(3) 0.4302(2) 0.3618(2) 0.0275(5) Uani 1 d . . C4 C -0.0905(3) 0.4841(3) 0.3674(2) 0.0362(6) Uani 1 d . . H4A H -0.0970(3) 0.5394(3) 0.3044(2) 0.054 Uiso 1 calc R . H4B H -0.1246(3) 0.5184(3) 0.4318(2) 0.054 Uiso 1 calc R . H4C H -0.1513(3) 0.4297(3) 0.3697(2) 0.054 Uiso 1 calc R . C5 C 0.2443(3) 0.3065(2) 0.4255(2) 0.0282(5) Uani 1 d . . C6 C 0.2766(4) 0.2182(2) 0.5136(2) 0.0387(7) Uani 1 d . . H6B H 0.1861(4) 0.2075(2) 0.5654(2) 0.058 Uiso 1 calc R . H6C H 0.3451(4) 0.2382(2) 0.5488(2) 0.058 Uiso 1 calc R . H6D H 0.3197(4) 0.1507(2) 0.4847(2) 0.058 Uiso 1 calc R . C7 C 0.1193(3) 0.5508(2) 0.1942(2) 0.0235(5) Uani 1 d . . C8 C 0.1578(4) 0.7044(2) 0.2754(2) 0.0387(7) Uani 1 d . . H8B H 0.1420(4) 0.7835(2) 0.2551(2) 0.058 Uiso 1 calc R . H8C H 0.2609(4) 0.6786(2) 0.2766(2) 0.058 Uiso 1 calc R . H8D H 0.0985(4) 0.6849(2) 0.3462(2) 0.058 Uiso 1 calc R . C9 C 0.0384(3) 0.6416(2) 0.0646(2) 0.0236(5) Uani 1 d . . C10 C -0.0731(3) 0.7623(2) -0.0777(2) 0.0245(5) Uani 1 d . . C11 C -0.0475(3) 0.8617(2) -0.0622(2) 0.0300(6) Uani 1 d . . H11B H 0.0116(3) 0.8641(2) -0.0140(2) 0.036 Uiso 1 calc R . C12 C -0.1091(4) 0.9571(2) -0.1179(2) 0.0362(6) Uani 1 d . . H12B H -0.0930(4) 1.0249(2) -0.1064(2) 0.043 Uiso 1 calc R . C13 C -0.1929(4) 0.9552(2) -0.1896(2) 0.0383(7) Uani 1 d . . H13A H -0.2335(4) 1.0211(2) -0.2278(2) 0.046 Uiso 1 calc R . C14 C -0.2176(3) 0.8567(2) -0.2056(2) 0.0372(6) Uani 1 d . . H14A H -0.2752(3) 0.8550(2) -0.2550(2) 0.045 Uiso 1 calc R . C15 C -0.1593(3) 0.7610(2) -0.1504(2) 0.0299(6) Uani 1 d . . H15A H -0.1776(3) 0.6937(2) -0.1617(2) 0.036 Uiso 1 calc R . C16 C 0.5489(3) 0.4298(2) 0.1599(2) 0.0246(5) Uani 1 d . . C17 C 0.6050(3) 0.3417(2) 0.0929(2) 0.0366(6) Uani 1 d . . H17A H 0.5230(3) 0.3172(2) 0.0767(2) 0.055 Uiso 1 calc R . H17B H 0.6612(3) 0.2807(2) 0.1316(2) 0.055 Uiso 1 calc R . H17C H 0.6677(3) 0.3694(2) 0.0263(2) 0.055 Uiso 1 calc R . C18 C 0.5793(3) 0.5550(2) 0.2523(2) 0.0241(5) Uani 1 d . . C19 C 0.6077(4) 0.7125(3) 0.1044(2) 0.0457(8) Uani 1 d . . H19A H 0.5876(4) 0.7914(3) 0.1021(2) 0.069 Uiso 1 calc R . H19B H 0.5497(4) 0.6917(3) 0.0612(2) 0.069 Uiso 1 calc R . H19C H 0.7114(4) 0.6899(3) 0.0759(2) 0.069 Uiso 1 calc R . C20 C 0.4879(3) 0.6449(2) 0.3779(2) 0.0232(5) Uani 1 d . . C21 C 0.3314(3) 0.7530(2) 0.5125(2) 0.0238(5) Uani 1 d . . C22 C 0.3022(3) 0.8500(2) 0.4443(2) 0.0299(6) Uani 1 d . . H22A H 0.3497(3) 0.8569(2) 0.3714(2) 0.036 Uiso 1 calc R . C23 C 0.2041(3) 0.9359(2) 0.4829(2) 0.0362(6) Uani 1 d . . H23A H 0.1848(3) 1.0014(2) 0.4359(2) 0.043 Uiso 1 calc R . C24 C 0.1336(3) 0.9280(2) 0.5887(2) 0.0361(6) Uani 1 d . . H24A H 0.0662(3) 0.9875(2) 0.6143(2) 0.043 Uiso 1 calc R . C25 C 0.1624(3) 0.8327(2) 0.6565(2) 0.0333(6) Uani 1 d . . H25A H 0.1145(3) 0.8266(2) 0.7294(2) 0.040 Uiso 1 calc R . C26 C 0.2597(3) 0.7461(2) 0.6198(2) 0.0263(5) Uani 1 d . . H26A H 0.2784(3) 0.6810(2) 0.6676(2) 0.032 Uiso 1 calc R . C50 C 0.3858(4) 1.0394(3) 0.7791(3) 0.0371(8) Uani 0.75 d P . C50A C 0.3125(15) 0.9747(12) 0.7966(11) 0.046(3) Uani 0.25 d P 1 Cl1 Cl 0.44580(10) 0.95678(8) 0.68126(8) 0.0539(3) Uani 1 d . . Cl2 Cl 0.20065(10) 1.09471(10) 0.79095(8) 0.0655(3) Uani 1 d . . Cl3 Cl 0.41279(14) 0.96788(11) 0.90450(9) 0.0798(4) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0228(10) 0.0290(10) 0.0202(10) -0.0029(8) -0.0074(8) -0.0029(8) N2 0.0302(11) 0.0356(12) 0.0248(11) -0.0012(9) -0.0062(9) -0.0099(9) N3 0.0240(10) 0.0280(10) 0.0231(10) -0.0040(8) -0.0089(8) -0.0021(8) N4 0.0276(10) 0.0284(11) 0.0258(11) -0.0056(8) -0.0124(9) 0.0000(8) N5 0.0303(11) 0.0298(11) 0.0253(11) -0.0045(8) -0.0131(9) 0.0008(8) N6 0.0366(12) 0.0278(11) 0.0262(11) -0.0065(9) -0.0158(9) 0.0001(9) N7 0.0244(10) 0.0297(11) 0.0201(10) -0.0024(8) -0.0057(8) -0.0022(8) N8 0.0241(10) 0.0313(11) 0.0205(10) -0.0046(8) -0.0018(8) -0.0025(8) N9 0.0236(10) 0.0277(10) 0.0184(10) -0.0033(8) -0.0029(8) -0.0006(8) N10 0.0342(11) 0.0293(11) 0.0174(10) -0.0026(8) -0.0003(9) -0.0076(9) N11 0.0334(11) 0.0295(11) 0.0192(10) -0.0055(8) -0.0003(9) -0.0072(9) N12 0.0330(11) 0.0270(10) 0.0162(10) -0.0016(8) -0.0051(8) 0.0011(9) C1 0.0249(12) 0.0265(11) 0.0209(11) -0.0055(9) -0.0090(9) -0.0026(9) C2 0.0289(12) 0.0283(12) 0.0243(12) -0.0026(10) -0.0107(10) -0.0035(10) C3 0.0262(12) 0.0346(13) 0.0250(12) -0.0057(10) -0.0065(10) -0.0096(10) C4 0.0248(13) 0.049(2) 0.0336(14) -0.0032(12) -0.0051(11) -0.0058(12) C5 0.0334(13) 0.0294(12) 0.0247(12) -0.0018(10) -0.0104(10) -0.0084(10) C6 0.047(2) 0.0352(14) 0.0331(15) 0.0058(12) -0.0124(13) -0.0100(12) C7 0.0215(11) 0.0277(12) 0.0219(11) -0.0041(9) -0.0070(9) -0.0018(9) C8 0.052(2) 0.0350(14) 0.039(2) -0.0101(12) -0.0255(14) -0.0046(12) C9 0.0217(11) 0.0275(12) 0.0211(11) -0.0038(9) -0.0063(9) -0.0004(9) C10 0.0237(11) 0.0291(12) 0.0181(11) -0.0016(9) -0.0021(9) -0.0029(9) C11 0.0374(14) 0.0317(13) 0.0211(12) -0.0030(10) -0.0073(11) -0.0059(11) C12 0.051(2) 0.0282(13) 0.0269(13) -0.0022(10) -0.0062(12) -0.0050(12) C13 0.048(2) 0.0313(14) 0.0306(14) 0.0023(11) -0.0121(13) 0.0048(12) C14 0.042(2) 0.040(2) 0.0291(14) -0.0022(12) -0.0162(12) 0.0011(12) C15 0.0343(13) 0.0315(13) 0.0248(12) -0.0027(10) -0.0099(11) -0.0043(11) C16 0.0268(12) 0.0280(12) 0.0158(10) -0.0013(9) -0.0029(9) -0.0009(9) C17 0.0382(15) 0.0380(15) 0.0328(15) -0.0151(12) -0.0040(12) 0.0010(12) C18 0.0183(10) 0.0321(12) 0.0211(11) -0.0035(9) -0.0031(9) -0.0036(9) C19 0.070(2) 0.040(2) 0.0196(13) -0.0004(11) 0.0080(14) -0.0161(15) C20 0.0219(11) 0.0264(11) 0.0212(11) -0.0040(9) -0.0051(9) -0.0028(9) C21 0.0236(11) 0.0264(12) 0.0216(11) -0.0031(9) -0.0055(9) -0.0041(9) C22 0.0338(13) 0.0303(13) 0.0210(12) 0.0006(10) -0.0032(10) -0.0014(10) C23 0.040(2) 0.0308(14) 0.0320(14) 0.0010(11) -0.0080(12) 0.0028(11) C24 0.0334(14) 0.0350(14) 0.0348(15) -0.0080(11) -0.0035(12) 0.0046(11) C25 0.0304(13) 0.0409(15) 0.0250(13) -0.0066(11) 0.0003(11) -0.0025(11) C26 0.0273(12) 0.0291(12) 0.0213(12) -0.0020(9) -0.0040(10) -0.0046(10) C50 0.030(2) 0.033(2) 0.043(2) -0.004(2) 0.000(2) -0.0042(15) C50A 0.039(7) 0.049(7) 0.046(7) -0.012(6) -0.003(6) -0.004(6) Cl1 0.0488(5) 0.0616(6) 0.0538(5) -0.0206(4) -0.0119(4) -0.0013(4) Cl2 0.0393(5) 0.0918(8) 0.0465(5) 0.0016(5) -0.0014(4) 0.0127(4) Cl3 0.0822(8) 0.0958(9) 0.0504(6) -0.0175(6) -0.0263(5) 0.0330(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.390(3) . ? N1 C1 1.406(3) . ? N1 C7 1.416(3) . ? N2 C3 1.282(3) . ? N2 C5 1.392(4) . ? N3 C7 1.320(3) . ? N3 C9 1.369(3) . ? N4 C7 1.320(3) . ? N4 N5 1.375(3) . ? N4 C8 1.457(3) . ? N5 C9 1.329(3) . ? N6 C9 1.367(3) . ? N6 C10 1.397(3) . ? N7 C1 1.288(3) . ? N7 C16 1.390(3) . ? N8 C16 1.290(3) . ? N8 C18 1.389(3) . ? N9 C18 1.332(3) . ? N9 C20 1.370(3) . ? N10 C18 1.328(3) . ? N10 N11 1.385(3) . ? N10 C19 1.445(4) . ? N11 C20 1.316(3) . ? N12 C20 1.366(3) . ? N12 C21 1.392(3) . ? C1 C2 1.428(3) . ? C2 C5 1.349(4) . ? C3 C4 1.493(4) . ? C5 C6 1.489(4) . ? C10 C11 1.394(4) . ? C10 C15 1.403(4) . ? C11 C12 1.390(4) . ? C12 C13 1.378(4) . ? C13 C14 1.382(5) . ? C14 C15 1.377(4) . ? C16 C17 1.493(4) . ? C21 C22 1.397(4) . ? C21 C26 1.402(4) . ? C22 C23 1.382(4) . ? C23 C24 1.382(4) . ? C24 C25 1.379(4) . ? C25 C26 1.377(4) . ? C50 C50A 1.141(15) . ? C50 Cl1 1.733(4) . ? C50 Cl2 1.754(4) . ? C50 Cl3 1.765(5) . ? C50A Cl2 1.681(14) . ? C50A Cl1 1.750(14) . ? C50A Cl3 1.866(15) . ? 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 C3 N1 C1 121.8(2) . . ? C3 N1 C7 120.1(2) . . ? C1 N1 C7 118.1(2) . . ? C3 N2 C5 117.9(2) . . ? C7 N3 C9 101.2(2) . . ? C7 N4 N5 109.1(2) . . ? C7 N4 C8 130.1(2) . . ? N5 N4 C8 120.8(2) . . ? C9 N5 N4 101.8(2) . . ? C9 N6 C10 127.7(2) . . ? C1 N7 C16 120.3(2) . . ? C16 N8 C18 116.2(2) . . ? C18 N9 C20 102.1(2) . . ? C18 N10 N11 109.7(2) . . ? C18 N10 C19 129.7(2) . . ? N11 N10 C19 120.6(2) . . ? C20 N11 N10 101.7(2) . . ? C20 N12 C21 127.2(2) . . ? N7 C1 N1 117.0(2) . . ? N7 C1 C2 129.1(2) . . ? N1 C1 C2 113.9(2) . . ? C5 C2 C1 120.7(2) . . ? N2 C3 N1 123.0(2) . . ? N2 C3 C4 120.6(2) . . ? N1 C3 C4 116.5(2) . . ? C2 C5 N2 122.7(2) . . ? C2 C5 C6 122.3(3) . . ? N2 C5 C6 115.0(2) . . ? N4 C7 N3 112.6(2) . . ? N4 C7 N1 122.0(2) . . ? N3 C7 N1 125.3(2) . . ? N5 C9 N6 125.4(2) . . ? N5 C9 N3 115.3(2) . . ? N6 C9 N3 119.3(2) . . ? C11 C10 N6 124.1(2) . . ? C11 C10 C15 119.1(2) . . ? N6 C10 C15 116.8(2) . . ? C12 C11 C10 119.4(3) . . ? C13 C12 C11 121.2(3) . . ? C12 C13 C14 119.4(3) . . ? C15 C14 C13 120.6(3) . . ? C14 C15 C10 120.2(3) . . ? N8 C16 N7 123.5(2) . . ? N8 C16 C17 119.5(2) . . ? N7 C16 C17 116.7(2) . . ? N10 C18 N9 111.0(2) . . ? N10 C18 N8 123.1(2) . . ? N9 C18 N8 125.9(2) . . ? N11 C20 N12 125.8(2) . . ? N11 C20 N9 115.5(2) . . ? N12 C20 N9 118.6(2) . . ? N12 C21 C22 123.9(2) . . ? N12 C21 C26 117.8(2) . . ? C22 C21 C26 118.3(2) . . ? C23 C22 C21 120.1(2) . . ? C22 C23 C24 121.1(3) . . ? C25 C24 C23 119.1(3) . . ? C26 C25 C24 120.7(3) . . ? C25 C26 C21 120.7(2) . . ? C50A C50 Cl1 71.7(7) . . ? C50A C50 Cl2 67.2(7) . . ? Cl1 C50 Cl2 112.3(2) . . ? C50A C50 Cl3 76.6(8) . . ? Cl1 C50 Cl3 111.3(2) . . ? Cl2 C50 Cl3 108.3(2) . . ? C50 C50A Cl2 74.1(8) . . ? C50 C50A Cl1 70.1(7) . . ? Cl2 C50A Cl1 115.1(8) . . ? C50 C50A Cl3 66.9(7) . . ? Cl2 C50A Cl3 107.0(7) . . ? Cl1 C50A Cl3 106.0(7) . . ? C50 Cl1 C50A 38.2(5) . . ? C50A Cl2 C50 38.7(5) . . ? C50 Cl3 C50A 36.5(5) . . ? _refine_diff_density_max 0.762 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.103 #===END