# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/185 data_global #Manuscript-Crystal Violet's Shoulder _publ_contact_author ; Bart Kahr Departement of Chemistry University of Washington Box 351700 Seattle WA 98195-1700 USA ; _publ_contact_author_email 'kahr@gibbs.chem.washington.edu' _publ_contact_author_fax '(206) 865-8665' _publ_contact_author_phone '(206) 616-8195' _publ_requested_journal 'Journal of the Chemical Society Perkin Transactions 2' loop_ _publ_author_name _publ_author_address 'Lovell, Scott' ;Departement of Chemistry University of Washington Box 351700 Seattle WA 98195-1700 USA ; 'Marquardt, Brian J.' ;Department of Chemistry University of Washington Box 351700 Seattle WA 98195-1700 USA ; 'Kahr, Bart' ;Department of Chemistry University of Washington Box 351700 Seattle WA 98195-1700 USA ; _publ_section_title ; Crystal Violet's Shoulder ; #-------------------------------------------------- #STRUCTURE #1 #-------------------------------------------------- data_shelxl1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'crystal violet chloride' _chemical_formula_moiety 'C25 H30 N3^+^ Cl^-^ * 9H2O' _chemical_formula_sum 'C25 H48 Cl N3 O9' _chemical_formula_weight 570.11 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' 'Cl' 'Cl' 0.1484 0.1585 '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 'trigonal' _symmetry_space_group_name_H-M 'P 3 1 c (No. 159)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, z+1/2' '-x, -x+y, z+1/2' 'x-y, -y, z+1/2' _cell_length_a 15.7087(4) _cell_length_b 15.7087(4) _cell_length_c 7.4783(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1598.14(7) _cell_formula_units_Z 2 _cell_measurement_temperature 161(2) _cell_measurement_reflns_used 688 _exptl_crystal_description prism _exptl_crystal_colour 'metallic green' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type none _exptl_special_details ; Data was collected by \w scans in 1^o^ increments over 180^o^ with 15 second exposures per frame. Crystal to detector distance was 28 mm. The instrument was set to zero before data collection. ; _diffrn_ambient_temperature 161(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 25709 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 28.74 _reflns_number_total 2451 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD' _computing_cell_refinement 'HKL SCALEPACK' _computing_data_reduction 'DENZO' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 4sigma(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. All H atoms were located by difference fourier synthesis and refined with a riding model. U~iso~ were fixed to be 1.1U~eq~ of their parent atom and 1.5U~eq~ for methyls and O-H's. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1065P)^2^+1.8679P] 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 'H atoms riding' _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(10) _refine_ls_number_reflns 2451 _refine_ls_number_parameters 112 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2278 _refine_ls_wR_factor_gt 0.2011 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6667 0.3333 0.4748(7) 0.0272(11) Uani 1 d S . . C2 C 0.7716(2) 0.3966(2) 0.4767(4) 0.0258(6) Uani 1 d . . . C3 C 0.9807(2) 0.5199(3) 0.4823(4) 0.0281(7) Uani 1 d . . . C4 C 0.9362(2) 0.4246(2) 0.4067(4) 0.0292(7) Uani 1 d . . . H4 H 0.9884 0.4155 0.3307 0.032 Uiso 1 d R . . C5 C 0.8354(2) 0.3659(2) 0.4017(4) 0.0276(7) Uani 1 d . . . H5 H 0.8061 0.2960 0.3309 0.030 Uiso 1 d R . . C6 C 0.9182(2) 0.5521(2) 0.5565(4) 0.0310(7) Uani 1 d . . . H6 H 0.9500 0.6237 0.6110 0.034 Uiso 1 d R . . C7 C 0.8180(2) 0.4921(2) 0.5533(4) 0.0273(7) Uani 1 d . . . H7 H 0.7783 0.5256 0.6100 0.030 Uiso 1 d R . . C8 C 1.1436(3) 0.5388(3) 0.4350(5) 0.0415(9) Uani 1 d . . . H8A H 1.2268 0.5951 0.4767 0.062 Uiso 1 d R . . H8B H 1.1295 0.4776 0.5368 0.062 Uiso 1 d R . . H8C H 1.1279 0.5121 0.2960 0.062 Uiso 1 d R . . C9 C 1.1254(3) 0.6783(3) 0.5496(5) 0.0414(9) Uani 1 d . . . H9A H 1.2024 0.7223 0.4938 0.062 Uiso 1 d R . . H9B H 1.1068 0.7205 0.4873 0.062 Uiso 1 d R . . H9C H 1.1326 0.6743 0.7130 0.062 Uiso 1 d R . . Cl1 Cl 1.0000 0.0000 0.252(3) 0.362(10) Uani 1 d S . . N1 N 1.08011(17) 0.57901(18) 0.4865(4) 0.0325(7) Uani 1 d . . . O1 O 1.00269(17) 0.81321(18) 0.2494(4) 0.1048(19) Uani 1 d R . . H1A H 0.9871 0.8358 0.3490 0.157 Uiso 1 d R . . H1B H 1.0018 0.8370 0.1523 0.157 Uiso 1 d R . . O2 O 0.8960(3) 0.2019(4) 0.7506(12) 0.128(2) Uani 1 d . . . H2A H 0.8895 0.1350 0.8193 0.192 Uiso 1 d R . . H2B H 0.9390 0.2405 0.6400 0.192 Uiso 1 d R . . O3 O 0.9025(5) 0.2054(6) 0.2104(18) 0.221(6) Uani 1 d . . . H3A H 0.8807 0.1756 0.3477 0.332 Uiso 1 d R . . H3B H 0.9772 0.2499 0.2457 0.332 Uiso 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0321(17) 0.0321(17) 0.017(2) 0.000 0.000 0.0160(9) C2 0.0274(15) 0.0264(15) 0.0237(13) 0.0023(12) -0.0002(12) 0.0134(12) C3 0.0274(15) 0.0341(16) 0.0239(14) 0.0031(12) 0.0031(12) 0.0162(13) C4 0.0276(15) 0.0301(16) 0.0318(17) 0.0041(13) 0.0043(13) 0.0158(14) C5 0.0307(16) 0.0274(15) 0.0258(15) -0.0004(12) 0.0002(12) 0.0154(13) C6 0.0307(17) 0.0266(16) 0.0367(18) -0.0018(13) -0.0041(13) 0.0151(14) C7 0.0256(15) 0.0291(15) 0.0280(16) -0.0004(12) 0.0006(12) 0.0141(13) C8 0.0308(18) 0.047(2) 0.047(2) 0.0048(17) 0.0038(15) 0.0201(17) C9 0.0299(17) 0.0338(18) 0.048(2) -0.0002(16) -0.0034(15) 0.0067(15) Cl1 0.229(7) 0.229(7) 0.63(3) 0.000 0.000 0.115(4) N1 0.0250(14) 0.0348(15) 0.0365(15) 0.0044(12) 0.0018(12) 0.0140(12) O1 0.056(2) 0.060(2) 0.193(6) -0.025(3) -0.040(3) 0.0250(19) O2 0.064(3) 0.091(4) 0.252(8) 0.034(4) 0.019(4) 0.055(3) O3 0.100(4) 0.133(5) 0.468(16) -0.170(8) -0.121(7) 0.086(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.438(3) . ? C2 C7 1.421(4) . ? C2 C5 1.425(4) . ? C3 N1 1.361(4) . ? C3 C4 1.415(5) . ? C3 C6 1.422(4) . ? C4 C5 1.378(4) . ? C6 C7 1.372(4) . ? C8 N1 1.474(5) . ? C9 N1 1.432(5) . ? 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 C1 C2 119.990(8) . 3_665 ? C2 C1 C2 119.992(9) . 2_655 ? C2 C1 C2 119.989(7) 3_665 2_655 ? C7 C2 C5 116.1(3) . . ? C7 C2 C1 122.6(3) . . ? C5 C2 C1 121.3(3) . . ? N1 C3 C4 121.5(3) . . ? N1 C3 C6 120.6(3) . . ? C4 C3 C6 117.9(3) . . ? C5 C4 C3 120.9(3) . . ? C4 C5 C2 122.0(3) . . ? C7 C6 C3 120.5(3) . . ? C6 C7 C2 122.6(3) . . ? C3 N1 C9 121.7(3) . . ? C3 N1 C8 119.5(3) . . ? C9 N1 C8 118.6(3) . . ? 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 C1 C2 C7 -150.8(3) 3_665 . . . ? C2 C1 C2 C7 27.2(7) 2_655 . . . ? C2 C1 C2 C5 28.8(7) 3_665 . . . ? C2 C1 C2 C5 -153.2(3) 2_655 . . . ? N1 C3 C4 C5 -179.4(3) . . . . ? C6 C3 C4 C5 1.5(5) . . . . ? C3 C4 C5 C2 -2.0(5) . . . . ? C7 C2 C5 C4 1.4(5) . . . . ? C1 C2 C5 C4 -178.3(3) . . . . ? N1 C3 C6 C7 -179.5(3) . . . . ? C4 C3 C6 C7 -0.3(5) . . . . ? C3 C6 C7 C2 -0.3(5) . . . . ? C5 C2 C7 C6 -0.2(5) . . . . ? C1 C2 C7 C6 179.4(4) . . . . ? C4 C3 N1 C9 174.9(3) . . . . ? C6 C3 N1 C9 -6.0(5) . . . . ? C4 C3 N1 C8 -8.7(5) . . . . ? C6 C3 N1 C8 170.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.394 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.098 #===END #-------------------------------------------------- #STRUCTURE #2 #-------------------------------------------------- data_shelxl2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'crystal violet chloride' _chemical_formula_moiety 'C25 H30 N3^+^ Cl^-^ *H2O' _chemical_formula_sum 'C25 H32 Cl N3 O' _chemical_formula_weight 425.99 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' 'Cl' 'Cl' 0.1484 0.1585 '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 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c (No. 14)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1887(5) _cell_length_b 21.4842(11) _cell_length_c 21.2594(6) _cell_angle_alpha 90 _cell_angle_beta 94.374(3) _cell_angle_gamma 90 _cell_volume 4640.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 161(2) _cell_measurement_reflns_used 263 _exptl_crystal_description needle _exptl_crystal_colour 'metallic green' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9447 _exptl_absorpt_correction_T_max 0.9853 _exptl_special_details ; Data was collected by \w scans in 1^o^ increments over 180^o^ with 60 second exposures per frame. Crystal-to- detector distance was 28 mm. The insturment was set to zero for all angles before data collection. ; _diffrn_ambient_temperature 161(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 61131 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.1025 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.14 _reflns_number_total 7690 _reflns_number_gt 4240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD' _computing_cell_refinement 'HKL SCALEPACK' _computing_data_reduction 'DENZO' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All H atoms were located by difference fourier synthesis and refined with a riding model. U~iso~ values were fixed to be 1.1U~eq~ of their parent atom and 1.5U~eq~ for methyl H's and water H's. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+2.9845P] 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 'H atoms riding' _refine_ls_extinction_method none _refine_ls_number_reflns 7690 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1462 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1933 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9950(4) 0.22974(19) 0.28031(18) 0.0360(10) Uani 1 d . . . C2 C 1.0050(4) 0.26866(18) 0.22582(17) 0.0338(9) Uani 1 d . . . C3 C 1.1030(4) 0.31501(19) 0.22436(19) 0.0380(10) Uani 1 d . . . H3 H 1.1711 0.3176 0.2608 0.042 Uiso 1 d R . . C4 C 1.1107(4) 0.3543(2) 0.17415(19) 0.0412(10) Uani 1 d . . . H4 H 1.1862 0.3854 0.1717 0.045 Uiso 1 d R . . C5 C 1.0186(4) 0.34934(19) 0.12004(18) 0.0375(10) Uani 1 d . . . C6 C 0.9237(4) 0.30135(19) 0.11943(18) 0.0381(10) Uani 1 d . . . H6 H 0.8413 0.2983 0.0868 0.042 Uiso 1 d R . . C7 C 0.9164(4) 0.26283(19) 0.17084(17) 0.0367(10) Uani 1 d . . . H7 H 0.8380 0.2315 0.1736 0.040 Uiso 1 d R . . C8 C 0.9383(4) 0.16849(18) 0.27410(17) 0.0340(9) Uani 1 d . . . C9 C 0.8571(4) 0.14456(19) 0.31965(19) 0.0387(10) Uani 1 d . . . H9 H 0.8547 0.1723 0.3561 0.043 Uiso 1 d R . . C10 C 0.7944(4) 0.08787(19) 0.31337(19) 0.0397(10) Uani 1 d . . . H10 H 0.7302 0.0707 0.3484 0.044 Uiso 1 d R . . C11 C 0.8145(4) 0.05003(19) 0.26043(18) 0.0370(10) Uani 1 d . . . C12 C 0.9010(4) 0.0711(2) 0.21598(18) 0.0401(10) Uani 1 d . . . H12 H 0.9276 0.0464 0.1802 0.044 Uiso 1 d R . . C13 C 0.9576(4) 0.1290(2) 0.22263(18) 0.0389(10) Uani 1 d . . . H13 H 1.0236 0.1427 0.1954 0.043 Uiso 1 d R . . C14 C 1.0409(4) 0.25160(19) 0.34224(17) 0.0342(10) Uani 1 d . . . C15 C 1.0263(4) 0.31462(19) 0.36077(18) 0.0355(10) Uani 1 d . . . H15 H 0.9778 0.3456 0.3279 0.039 Uiso 1 d R . . C16 C 1.0663(4) 0.3341(2) 0.42093(18) 0.0387(10) Uani 1 d . . . H16 H 1.0333 0.3729 0.4362 0.043 Uiso 1 d R . . C17 C 1.1266(4) 0.2925(2) 0.46572(17) 0.0359(10) Uani 1 d . . . C18 C 1.1472(4) 0.23022(19) 0.44681(18) 0.0379(10) Uani 1 d . . . H18 H 1.1864 0.1985 0.4735 0.042 Uiso 1 d R . . C19 C 1.1003(4) 0.21066(19) 0.38742(17) 0.0355(10) Uani 1 d . . . H19 H 1.1208 0.1657 0.3765 0.039 Uiso 1 d R . . C20 C 0.9443(5) 0.3819(2) 0.01130(19) 0.0516(12) Uani 1 d . . . H20A H 0.9304 0.3360 -0.0017 0.077 Uiso 1 d R . . H20B H 0.9851 0.4008 -0.0271 0.077 Uiso 1 d R . . H20C H 0.8371 0.3915 0.0183 0.077 Uiso 1 d R . . C21 C 1.0990(5) 0.4482(2) 0.0785(2) 0.0632(14) Uani 1 d . . . H21A H 1.0916 0.4703 0.1260 0.095 Uiso 1 d R . . H21B H 1.2102 0.4409 0.0807 0.095 Uiso 1 d R . . H21C H 1.0897 0.4777 0.0358 0.095 Uiso 1 d R . . C22 C 0.7679(5) -0.0415(2) 0.1939(2) 0.0516(12) Uani 1 d . . . H22A H 0.7077 -0.0791 0.2000 0.077 Uiso 1 d R . . H22B H 0.8667 -0.0507 0.1878 0.077 Uiso 1 d R . . H22C H 0.7182 -0.0245 0.1573 0.077 Uiso 1 d R . . C23 C 0.6383(5) -0.0205(2) 0.2869(2) 0.0557(13) Uani 1 d . . . H23A H 0.6613 -0.0125 0.3360 0.084 Uiso 1 d R . . H23B H 0.5990 -0.0623 0.2791 0.084 Uiso 1 d R . . H23C H 0.5557 0.0063 0.2693 0.084 Uiso 1 d R . . C24 C 1.1353(5) 0.3756(2) 0.5470(2) 0.0492(12) Uani 1 d . . . H24A H 1.0313 0.3830 0.5404 0.074 Uiso 1 d R . . H24B H 1.1522 0.4139 0.5189 0.074 Uiso 1 d R . . H24C H 1.1648 0.3772 0.6018 0.074 Uiso 1 d R . . C25 C 1.2371(5) 0.2734(2) 0.5715(2) 0.0550(13) Uani 1 d . . . H25A H 1.3143 0.3011 0.5968 0.082 Uiso 1 d R . . H25B H 1.2801 0.2318 0.5575 0.082 Uiso 1 d R . . H25C H 1.1538 0.2702 0.6036 0.082 Uiso 1 d R . . C26 C 1.4950(4) 0.2050(2) 0.24505(17) 0.0357(10) Uani 1 d . . . C27 C 1.5433(4) 0.21061(19) 0.18301(17) 0.0352(10) Uani 1 d . . . C28 C 1.5314(4) 0.26642(19) 0.14812(17) 0.0366(10) Uani 1 d . . . H28 H 1.4787 0.3073 0.1719 0.040 Uiso 1 d R . . C29 C 1.5714(4) 0.2710(2) 0.08786(18) 0.0378(10) Uani 1 d . . . H29 H 1.5522 0.3103 0.0634 0.042 Uiso 1 d R . . C30 C 1.6326(4) 0.2199(2) 0.06015(17) 0.0364(10) Uani 1 d . . . C31 C 1.6496(4) 0.1640(2) 0.09547(17) 0.0392(10) Uani 1 d . . . H31 H 1.6900 0.1283 0.0751 0.043 Uiso 1 d R . . C32 C 1.6038(4) 0.15956(19) 0.15426(17) 0.0368(10) Uani 1 d . . . H32 H 1.6085 0.1187 0.1751 0.040 Uiso 1 d R . . C33 C 1.4358(4) 0.14791(19) 0.26355(18) 0.0367(10) Uani 1 d . . . C34 C 1.3618(4) 0.11031(19) 0.21916(17) 0.0358(10) Uani 1 d . . . H34 H 1.3638 0.1214 0.1688 0.039 Uiso 1 d R . . C35 C 1.2944(4) 0.0584(2) 0.23655(18) 0.0389(10) Uani 1 d . . . H35 H 1.2366 0.0320 0.1968 0.043 Uiso 1 d R . . C36 C 1.3052(4) 0.0381(2) 0.30042(18) 0.0405(10) Uani 1 d . . . C37 C 1.3796(4) 0.0752(2) 0.34502(18) 0.0442(11) Uani 1 d . . . H37 H 1.4053 0.0603 0.3878 0.049 Uiso 1 d R . . C38 C 1.4401(4) 0.1283(2) 0.32685(17) 0.0393(10) Uani 1 d . . . H38 H 1.4932 0.1526 0.3619 0.043 Uiso 1 d R . . C39 C 1.5014(4) 0.25817(19) 0.28691(18) 0.0368(10) Uani 1 d . . . C40 C 1.4069(4) 0.2657(2) 0.33170(18) 0.0410(11) Uani 1 d . . . H40 H 1.3277 0.2288 0.3367 0.045 Uiso 1 d R . . C41 C 1.4086(4) 0.3159(2) 0.37165(19) 0.0426(11) Uani 1 d . . . H41 H 1.3251 0.3264 0.4016 0.047 Uiso 1 d R . . C42 C 1.5030(4) 0.3626(2) 0.36901(18) 0.0409(11) Uani 1 d . . . C43 C 1.5999(4) 0.3553(2) 0.32504(19) 0.0441(11) Uani 1 d . . . H43 H 1.6742 0.3896 0.3217 0.049 Uiso 1 d R . . C44 C 1.5982(4) 0.3047(2) 0.28506(18) 0.0405(10) Uani 1 d . . . H44 H 1.6754 0.3015 0.2534 0.045 Uiso 1 d R . . C45 C 1.7647(5) 0.1793(3) -0.0220(2) 0.0608(14) Uani 1 d . . . H45A H 1.7061 0.1377 -0.0281 0.091 Uiso 1 d R . . H45B H 1.7747 0.1777 -0.0628 0.091 Uiso 1 d R . . H45C H 1.8518 0.1801 0.0132 0.091 Uiso 1 d R . . C46 C 1.6430(5) 0.2797(2) -0.03741(19) 0.0566(13) Uani 1 d . . . H46A H 1.5501 0.2918 -0.0306 0.085 Uiso 1 d R . . H46B H 1.6501 0.2763 -0.0705 0.085 Uiso 1 d R . . H46C H 1.7176 0.3213 -0.0340 0.085 Uiso 1 d R . . C47 C 1.2710(6) -0.0365(3) 0.3845(2) 0.0787(19) Uani 1 d . . . H47A H 1.2408 -0.0777 0.3884 0.118 Uiso 1 d R . . H47B H 1.3796 -0.0405 0.3977 0.118 Uiso 1 d R . . H47C H 1.2054 -0.0016 0.4121 0.118 Uiso 1 d R . . C48 C 1.1594(5) -0.0526(2) 0.2768(2) 0.0506(12) Uani 1 d . . . H48A H 1.0571 -0.0439 0.2889 0.076 Uiso 1 d R . . H48B H 1.1458 -0.0405 0.2285 0.076 Uiso 1 d R . . H48C H 1.1960 -0.1047 0.2852 0.076 Uiso 1 d R . . C49 C 1.5699(6) 0.4706(3) 0.3948(3) 0.0697(16) Uani 1 d . . . H49A H 1.6589 0.4703 0.4252 0.105 Uiso 1 d R . . H49B H 1.5825 0.4715 0.3491 0.105 Uiso 1 d R . . H49C H 1.5091 0.5099 0.4113 0.105 Uiso 1 d R . . C50 C 1.4204(6) 0.4159(3) 0.4604(2) 0.0699(16) Uani 1 d . . . H50A H 1.4214 0.3748 0.4785 0.105 Uiso 1 d R . . H50B H 1.3081 0.4225 0.4379 0.105 Uiso 1 d R . . H50C H 1.4419 0.4437 0.5044 0.105 Uiso 1 d R . . Cl1 Cl 0.91467(12) 0.47710(6) 0.39168(5) 0.0524(3) Uani 1 d . . . H1A H 1.0910 0.5180 0.4506 0.079 Uiso 1 d R . . H1B H 1.1445 0.5300 0.5020 0.079 Uiso 1 d R . . Cl2 Cl 1.39134(15) 0.39801(6) 0.01609(6) 0.0683(4) Uani 1 d . . . H2A H 1.6448 0.0014 0.4650 0.102 Uiso 1 d R . . H2B H 1.5804 0.0668 0.4733 0.102 Uiso 1 d R . . O1 O 1.1792(3) 0.52966(15) 0.46534(14) 0.0558(9) Uani 1 d . . . O2 O 1.6494(3) 0.04543(16) 0.45758(14) 0.0590(9) Uani 1 d . . . N1 N 1.0221(4) 0.39012(17) 0.07153(15) 0.0443(9) Uani 1 d . . . N2 N 0.7524(4) -0.00644(16) 0.25241(16) 0.0441(9) Uani 1 d . . . N3 N 1.1649(4) 0.31248(17) 0.52515(16) 0.0461(9) Uani 1 d . . . N4 N 1.6728(4) 0.22451(18) 0.00037(15) 0.0463(10) Uani 1 d . . . N5 N 1.2499(4) -0.01539(18) 0.31820(16) 0.0537(11) Uani 1 d . . . N6 N 1.5024(4) 0.41321(18) 0.40754(17) 0.0541(11) 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 C1 0.034(2) 0.035(3) 0.040(2) 0.0007(18) 0.0087(18) 0.003(2) C2 0.034(2) 0.031(2) 0.036(2) 0.0022(17) 0.0030(18) -0.0005(19) C3 0.037(3) 0.036(3) 0.042(2) 0.0029(18) 0.0022(19) -0.001(2) C4 0.039(3) 0.040(3) 0.045(2) 0.001(2) 0.005(2) -0.010(2) C5 0.039(3) 0.039(3) 0.035(2) -0.0015(18) 0.0072(19) -0.001(2) C6 0.036(3) 0.040(3) 0.038(2) -0.0058(19) -0.0009(18) -0.002(2) C7 0.035(2) 0.037(3) 0.039(2) -0.0059(18) 0.0041(18) -0.0076(19) C8 0.038(2) 0.031(2) 0.033(2) 0.0005(17) 0.0044(18) 0.0009(19) C9 0.043(3) 0.034(3) 0.039(2) -0.0017(18) 0.0023(19) 0.001(2) C10 0.037(3) 0.035(3) 0.048(2) 0.0034(19) 0.006(2) -0.003(2) C11 0.038(3) 0.029(2) 0.043(2) 0.0009(18) -0.0029(19) 0.006(2) C12 0.046(3) 0.037(3) 0.038(2) -0.0034(19) 0.007(2) 0.001(2) C13 0.038(3) 0.041(3) 0.038(2) 0.0011(19) 0.0062(19) -0.004(2) C14 0.036(2) 0.033(2) 0.034(2) -0.0013(18) 0.0038(18) -0.0028(19) C15 0.035(2) 0.034(3) 0.038(2) 0.0029(18) 0.0045(18) 0.0003(19) C16 0.039(3) 0.032(2) 0.045(2) -0.0043(19) 0.005(2) 0.002(2) C17 0.031(2) 0.042(3) 0.034(2) 0.0000(19) 0.0005(18) -0.002(2) C18 0.039(3) 0.035(3) 0.040(2) 0.0043(18) 0.0035(19) -0.003(2) C19 0.039(3) 0.030(2) 0.038(2) -0.0012(18) 0.0053(19) -0.0022(19) C20 0.064(3) 0.054(3) 0.037(2) -0.001(2) 0.002(2) 0.000(3) C21 0.067(4) 0.057(3) 0.064(3) 0.017(3) -0.002(3) -0.018(3) C22 0.064(3) 0.035(3) 0.054(3) -0.009(2) -0.008(2) -0.009(2) C23 0.045(3) 0.046(3) 0.075(3) 0.002(2) 0.003(2) -0.010(2) C24 0.055(3) 0.043(3) 0.048(3) -0.007(2) -0.008(2) 0.006(2) C25 0.059(3) 0.050(3) 0.053(3) 0.000(2) -0.018(2) 0.005(3) C26 0.027(2) 0.046(3) 0.033(2) -0.0001(18) -0.0028(17) 0.003(2) C27 0.031(2) 0.042(3) 0.034(2) 0.0018(18) 0.0037(18) -0.006(2) C28 0.037(3) 0.037(3) 0.036(2) 0.0023(18) 0.0004(18) -0.004(2) C29 0.036(2) 0.040(3) 0.036(2) 0.0062(18) 0.0017(18) -0.004(2) C30 0.033(2) 0.046(3) 0.030(2) -0.0002(18) 0.0024(18) -0.006(2) C31 0.040(3) 0.042(3) 0.035(2) -0.0025(19) 0.0001(19) -0.001(2) C32 0.039(3) 0.035(2) 0.036(2) 0.0044(18) 0.0014(19) -0.004(2) C33 0.036(2) 0.040(3) 0.035(2) 0.0013(18) 0.0013(18) -0.004(2) C34 0.040(3) 0.040(3) 0.027(2) 0.0033(17) 0.0023(18) 0.001(2) C35 0.039(3) 0.043(3) 0.035(2) -0.0003(19) 0.0036(18) 0.000(2) C36 0.038(3) 0.047(3) 0.036(2) 0.006(2) 0.0041(19) -0.006(2) C37 0.054(3) 0.049(3) 0.028(2) 0.0051(19) -0.001(2) -0.008(2) C38 0.045(3) 0.044(3) 0.029(2) 0.0007(18) 0.0018(19) -0.001(2) C39 0.036(2) 0.040(3) 0.034(2) -0.0001(18) 0.0039(18) 0.003(2) C40 0.038(3) 0.048(3) 0.037(2) 0.005(2) 0.0057(19) 0.000(2) C41 0.041(3) 0.047(3) 0.041(2) 0.003(2) 0.009(2) 0.006(2) C42 0.048(3) 0.040(3) 0.035(2) 0.0000(19) 0.006(2) 0.003(2) C43 0.047(3) 0.045(3) 0.041(2) 0.001(2) 0.008(2) -0.010(2) C44 0.040(3) 0.047(3) 0.035(2) 0.000(2) 0.0048(19) -0.006(2) C45 0.052(3) 0.093(4) 0.038(3) -0.002(2) 0.008(2) 0.015(3) C46 0.067(3) 0.069(4) 0.035(2) 0.010(2) 0.013(2) -0.010(3) C47 0.100(5) 0.079(4) 0.055(3) 0.026(3) -0.005(3) -0.046(4) C48 0.057(3) 0.047(3) 0.047(3) 0.001(2) 0.000(2) -0.012(2) C49 0.072(4) 0.066(4) 0.073(3) -0.019(3) 0.016(3) -0.014(3) C50 0.099(5) 0.064(4) 0.050(3) -0.008(2) 0.030(3) 0.011(3) Cl1 0.0617(8) 0.0504(7) 0.0446(6) 0.0036(5) 0.0007(5) 0.0093(6) Cl2 0.0814(10) 0.0537(8) 0.0705(8) 0.0123(6) 0.0098(7) -0.0012(7) O1 0.050(2) 0.066(2) 0.0519(18) 0.0067(16) 0.0088(15) 0.0009(17) O2 0.056(2) 0.062(2) 0.059(2) 0.0102(16) 0.0050(16) 0.0007(17) N1 0.048(2) 0.043(2) 0.042(2) 0.0084(17) 0.0021(17) -0.0103(18) N2 0.044(2) 0.034(2) 0.053(2) -0.0020(16) 0.0000(18) -0.0032(18) N3 0.053(2) 0.037(2) 0.046(2) 0.0010(17) -0.0098(18) 0.0034(18) N4 0.050(2) 0.057(3) 0.033(2) 0.0027(17) 0.0081(17) 0.0010(19) N5 0.067(3) 0.055(3) 0.038(2) 0.0142(18) -0.0009(19) -0.023(2) N6 0.063(3) 0.049(3) 0.050(2) -0.0117(19) 0.011(2) -0.003(2) _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 C1 C2 1.439(5) . ? C1 C8 1.439(6) . ? C1 C14 1.442(5) . ? C2 C3 1.412(6) . ? C2 C7 1.427(5) . ? C3 C4 1.367(5) . ? C4 C5 1.432(6) . ? C5 N1 1.356(5) . ? C5 C6 1.413(6) . ? C6 C7 1.377(5) . ? C8 C13 1.410(5) . ? C8 C9 1.418(5) . ? C9 C10 1.377(6) . ? C10 C11 1.416(6) . ? C11 N2 1.373(5) . ? C11 C12 1.415(5) . ? C12 C13 1.374(6) . ? C14 C19 1.405(5) . ? C14 C15 1.421(5) . ? C15 C16 1.377(5) . ? C16 C17 1.413(6) . ? C17 N3 1.363(5) . ? C17 C18 1.416(6) . ? C18 C19 1.381(5) . ? C20 N1 1.464(5) . ? C21 N1 1.476(6) . ? C22 N2 1.472(5) . ? C23 N2 1.453(5) . ? C24 N3 1.472(6) . ? C25 N3 1.452(5) . ? C26 C33 1.435(6) . ? C26 C27 1.448(5) . ? C26 C39 1.447(6) . ? C27 C28 1.410(6) . ? C27 C32 1.419(6) . ? C28 C29 1.377(5) . ? C29 C30 1.412(6) . ? C30 N4 1.368(5) . ? C30 C31 1.420(6) . ? C31 C32 1.370(5) . ? C33 C38 1.408(5) . ? C33 C34 1.415(6) . ? C34 C35 1.375(6) . ? C35 C36 1.422(5) . ? C36 N5 1.347(5) . ? C36 C37 1.414(6) . ? C37 C38 1.366(6) . ? C39 C44 1.407(6) . ? C39 C40 1.414(5) . ? C40 C41 1.371(6) . ? C41 C42 1.395(6) . ? C42 N6 1.361(5) . ? C42 C43 1.419(6) . ? C43 C44 1.380(6) . ? C45 N4 1.454(6) . ? C46 N4 1.451(6) . ? C47 N5 1.482(5) . ? C48 N5 1.463(6) . ? C49 N6 1.447(6) . ? C50 N6 1.451(6) . ? 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 C1 C8 120.7(3) . . ? C2 C1 C14 120.5(4) . . ? C8 C1 C14 118.8(3) . . ? C3 C2 C7 116.6(3) . . ? C3 C2 C1 121.4(4) . . ? C7 C2 C1 122.0(4) . . ? C4 C3 C2 122.3(4) . . ? C3 C4 C5 120.6(4) . . ? N1 C5 C6 121.5(4) . . ? N1 C5 C4 120.7(4) . . ? C6 C5 C4 117.9(4) . . ? C7 C6 C5 120.6(4) . . ? C6 C7 C2 121.9(4) . . ? C13 C8 C9 115.8(4) . . ? C13 C8 C1 122.9(3) . . ? C9 C8 C1 121.3(3) . . ? C10 C9 C8 123.0(4) . . ? C9 C10 C11 119.4(4) . . ? N2 C11 C12 120.3(4) . . ? N2 C11 C10 120.9(4) . . ? C12 C11 C10 118.8(4) . . ? C13 C12 C11 119.9(4) . . ? C12 C13 C8 122.8(4) . . ? C19 C14 C15 117.1(4) . . ? C19 C14 C1 120.9(4) . . ? C15 C14 C1 122.0(4) . . ? C16 C15 C14 121.1(4) . . ? C15 C16 C17 121.1(4) . . ? N3 C17 C16 120.3(4) . . ? N3 C17 C18 121.5(4) . . ? C16 C17 C18 118.2(4) . . ? C19 C18 C17 119.9(4) . . ? C18 C19 C14 122.4(4) . . ? C33 C26 C27 120.0(4) . . ? C33 C26 C39 120.4(3) . . ? C27 C26 C39 119.5(4) . . ? C28 C27 C32 117.0(3) . . ? C28 C27 C26 121.9(4) . . ? C32 C27 C26 121.1(4) . . ? C29 C28 C27 122.0(4) . . ? C28 C29 C30 120.3(4) . . ? N4 C30 C29 120.3(4) . . ? N4 C30 C31 121.2(4) . . ? C29 C30 C31 118.4(4) . . ? C32 C31 C30 120.3(4) . . ? C31 C32 C27 121.9(4) . . ? C38 C33 C34 116.3(4) . . ? C38 C33 C26 122.3(4) . . ? C34 C33 C26 121.3(3) . . ? C35 C34 C33 122.4(4) . . ? C34 C35 C36 120.1(4) . . ? N5 C36 C37 120.5(4) . . ? N5 C36 C35 121.7(4) . . ? C37 C36 C35 117.8(4) . . ? C38 C37 C36 120.8(4) . . ? C37 C38 C33 122.6(4) . . ? C44 C39 C40 116.8(4) . . ? C44 C39 C26 122.9(4) . . ? C40 C39 C26 120.3(4) . . ? C41 C40 C39 122.1(4) . . ? C40 C41 C42 121.1(4) . . ? N6 C42 C41 121.0(4) . . ? N6 C42 C43 121.3(4) . . ? C41 C42 C43 117.7(4) . . ? C44 C43 C42 121.1(4) . . ? C43 C44 C39 121.3(4) . . ? C5 N1 C20 122.9(4) . . ? C5 N1 C21 121.0(4) . . ? C20 N1 C21 116.0(3) . . ? C11 N2 C23 120.0(4) . . ? C11 N2 C22 118.6(3) . . ? C23 N2 C22 117.5(4) . . ? C17 N3 C25 122.8(4) . . ? C17 N3 C24 122.1(4) . . ? C25 N3 C24 115.1(3) . . ? C30 N4 C46 120.5(4) . . ? C30 N4 C45 120.1(4) . . ? C46 N4 C45 118.6(4) . . ? C36 N5 C48 123.7(3) . . ? C36 N5 C47 119.7(4) . . ? C48 N5 C47 116.4(4) . . ? C42 N6 C49 122.9(4) . . ? C42 N6 C50 121.8(4) . . ? C49 N6 C50 114.9(4) . . ? 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 C8 C1 C2 C3 -153.4(4) . . . . ? C14 C1 C2 C3 27.0(6) . . . . ? C8 C1 C2 C7 27.0(6) . . . . ? C14 C1 C2 C7 -152.6(4) . . . . ? C7 C2 C3 C4 2.5(6) . . . . ? C1 C2 C3 C4 -177.1(4) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 N1 176.8(4) . . . . ? C3 C4 C5 C6 -2.3(6) . . . . ? N1 C5 C6 C7 -175.9(4) . . . . ? C4 C5 C6 C7 3.3(6) . . . . ? C5 C6 C7 C2 -1.3(6) . . . . ? C3 C2 C7 C6 -1.6(6) . . . . ? C1 C2 C7 C6 178.0(4) . . . . ? C2 C1 C8 C13 37.3(6) . . . . ? C14 C1 C8 C13 -143.1(4) . . . . ? C2 C1 C8 C9 -141.7(4) . . . . ? C14 C1 C8 C9 37.9(6) . . . . ? C13 C8 C9 C10 -3.3(6) . . . . ? C1 C8 C9 C10 175.8(4) . . . . ? C8 C9 C10 C11 2.3(6) . . . . ? C9 C10 C11 N2 -179.3(4) . . . . ? C9 C10 C11 C12 1.3(6) . . . . ? N2 C11 C12 C13 176.7(4) . . . . ? C10 C11 C12 C13 -3.9(6) . . . . ? C11 C12 C13 C8 2.9(7) . . . . ? C9 C8 C13 C12 0.6(6) . . . . ? C1 C8 C13 C12 -178.5(4) . . . . ? C2 C1 C14 C19 -144.3(4) . . . . ? C8 C1 C14 C19 36.0(5) . . . . ? C2 C1 C14 C15 36.9(6) . . . . ? C8 C1 C14 C15 -142.7(4) . . . . ? C19 C14 C15 C16 -1.3(6) . . . . ? C1 C14 C15 C16 177.5(4) . . . . ? C14 C15 C16 C17 1.8(6) . . . . ? C15 C16 C17 N3 -179.7(4) . . . . ? C15 C16 C17 C18 1.2(6) . . . . ? N3 C17 C18 C19 176.3(4) . . . . ? C16 C17 C18 C19 -4.6(6) . . . . ? C17 C18 C19 C14 5.2(6) . . . . ? C15 C14 C19 C18 -2.2(6) . . . . ? C1 C14 C19 C18 179.0(4) . . . . ? C33 C26 C27 C28 142.8(4) . . . . ? C39 C26 C27 C28 -34.4(6) . . . . ? C33 C26 C27 C32 -36.5(6) . . . . ? C39 C26 C27 C32 146.3(4) . . . . ? C32 C27 C28 C29 2.6(6) . . . . ? C26 C27 C28 C29 -176.7(4) . . . . ? C27 C28 C29 C30 -3.3(6) . . . . ? C28 C29 C30 N4 -179.8(4) . . . . ? C28 C29 C30 C31 1.0(6) . . . . ? N4 C30 C31 C32 -177.3(4) . . . . ? C29 C30 C31 C32 1.9(6) . . . . ? C30 C31 C32 C27 -2.6(6) . . . . ? C28 C27 C32 C31 0.4(6) . . . . ? C26 C27 C32 C31 179.7(4) . . . . ? C27 C26 C33 C38 151.1(4) . . . . ? C39 C26 C33 C38 -31.8(6) . . . . ? C27 C26 C33 C34 -33.3(6) . . . . ? C39 C26 C33 C34 143.8(4) . . . . ? C38 C33 C34 C35 1.8(6) . . . . ? C26 C33 C34 C35 -174.1(4) . . . . ? C33 C34 C35 C36 -4.6(6) . . . . ? C34 C35 C36 N5 -174.2(4) . . . . ? C34 C35 C36 C37 4.1(6) . . . . ? N5 C36 C37 C38 177.5(4) . . . . ? C35 C36 C37 C38 -0.9(7) . . . . ? C36 C37 C38 C33 -2.0(7) . . . . ? C34 C33 C38 C37 1.6(6) . . . . ? C26 C33 C38 C37 177.4(4) . . . . ? C33 C26 C39 C44 153.9(4) . . . . ? C27 C26 C39 C44 -29.0(6) . . . . ? C33 C26 C39 C40 -27.0(6) . . . . ? C27 C26 C39 C40 150.1(4) . . . . ? C44 C39 C40 C41 0.0(6) . . . . ? C26 C39 C40 C41 -179.1(4) . . . . ? C39 C40 C41 C42 1.2(7) . . . . ? C40 C41 C42 N6 178.2(4) . . . . ? C40 C41 C42 C43 -2.1(6) . . . . ? N6 C42 C43 C44 -178.4(4) . . . . ? C41 C42 C43 C44 1.9(6) . . . . ? C42 C43 C44 C39 -0.7(7) . . . . ? C40 C39 C44 C43 -0.3(6) . . . . ? C26 C39 C44 C43 178.9(4) . . . . ? C6 C5 N1 C20 -10.4(6) . . . . ? C4 C5 N1 C20 170.5(4) . . . . ? C6 C5 N1 C21 165.3(4) . . . . ? C4 C5 N1 C21 -13.8(6) . . . . ? C12 C11 N2 C23 -162.9(4) . . . . ? C10 C11 N2 C23 17.7(6) . . . . ? C12 C11 N2 C22 -5.7(6) . . . . ? C10 C11 N2 C22 174.9(4) . . . . ? C16 C17 N3 C25 -174.7(4) . . . . ? C18 C17 N3 C25 4.4(6) . . . . ? C16 C17 N3 C24 5.6(6) . . . . ? C18 C17 N3 C24 -175.3(4) . . . . ? C29 C30 N4 C46 -5.4(6) . . . . ? C31 C30 N4 C46 173.8(4) . . . . ? C29 C30 N4 C45 164.0(4) . . . . ? C31 C30 N4 C45 -16.8(6) . . . . ? C37 C36 N5 C48 172.6(4) . . . . ? C35 C36 N5 C48 -9.1(7) . . . . ? C37 C36 N5 C47 -2.2(7) . . . . ? C35 C36 N5 C47 176.1(5) . . . . ? C41 C42 N6 C49 -160.9(5) . . . . ? C43 C42 N6 C49 19.4(7) . . . . ? C41 C42 N6 C50 11.5(7) . . . . ? C43 C42 N6 C50 -168.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.729 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.729 _refine_diff_density_max 0.293 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.056