# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Gale, Philip' 'Camiolo, Salvatore' 'Hursthouse, Michael B.' 'Light, Mark E.' 'Shi, Andy J.' _publ_contact_author_name 'Dr Philip Gale' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton Hants SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email 'PHILIP.GALE@SOTON.AC.UK' _publ_section_title ; Solution and solid-state studies of 3,4-dichloro-2,5-diamidopyrroles: formation of an unusual anionic narcissistic dimer ; data_s92 _database_code_CSD 178607 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 Cl2 N3 O2' _chemical_formula_weight 374.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 33.485(2) _cell_length_b 7.9757(4) _cell_length_c 12.4468(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3324.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13422 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 25.03 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9413 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymetric unit' _diffrn_detector_area_resol_mean '9.091 pixels mm^1^' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13422 _diffrn_reflns_av_R_equivalents 0.1635 _diffrn_reflns_av_sigmaI/netI 0.1972 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2792 _reflns_number_gt 1333 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; COLLECT (Hooft, 1998) ; _computing_cell_refinement ; SCALEPACK (Otwinoski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinoski and Minor, 1997), COLLECT (Hooft, 1998) MAXUS (Mackay et al., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2792 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2061 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.293 _refine_ls_restrained_S_all 1.293 _refine_ls_shift/su_max 0.283 _refine_ls_shift/su_mean 0.018 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 C1 C 0.35975(18) 0.4709(8) 0.0280(5) 0.0334(18) Uani 1 1 d . . . C2 C 0.32233(19) 0.5428(9) 0.0170(6) 0.0412(19) Uani 1 1 d . . . C3 C 0.31287(19) 0.6371(9) -0.0754(5) 0.039(2) Uani 1 1 d . . . C4 C 0.34146(18) 0.6575(8) -0.1568(5) 0.0375(19) Uani 1 1 d . . . C5 C 0.37955(17) 0.5823(8) -0.1478(5) 0.0327(17) Uani 1 1 d . . . C6 C 0.38823(16) 0.4916(8) -0.0544(5) 0.0249(17) Uani 1 1 d . . . C7 C 0.45876(17) 0.4175(8) -0.1000(5) 0.0247(16) Uani 1 1 d . . . C8 C 0.49324(16) 0.3188(8) -0.0603(4) 0.0183(15) Uani 1 1 d . . . C9 C 0.50129(17) 0.2262(8) 0.0303(4) 0.0237(16) Uani 1 1 d . . . C10 C 0.54033(17) 0.1617(7) 0.0209(4) 0.0237(17) Uani 1 1 d . . . C11 C 0.55510(18) 0.2158(8) -0.0772(5) 0.0242(16) Uani 1 1 d . . . C12 C 0.59133(17) 0.1819(8) -0.1397(5) 0.0234(16) Uani 1 1 d . . . C13 C 0.65886(16) 0.0505(8) -0.1326(5) 0.0309(17) Uani 1 1 d . . . C14 C 0.67308(17) 0.1170(8) -0.2305(5) 0.0324(18) Uani 1 1 d . . . C15 C 0.71080(18) 0.0573(9) -0.2675(5) 0.0382(19) Uani 1 1 d . . . C16 C 0.73274(18) -0.0593(9) -0.2097(5) 0.0377(18) Uani 1 1 d . . . C17 C 0.71801(19) -0.1208(8) -0.1117(6) 0.0415(19) Uani 1 1 d . . . C18 C 0.67995(18) -0.0679(8) -0.0726(5) 0.0348(18) Uani 1 1 d . . . N1 N 0.42574(13) 0.4148(6) -0.0369(4) 0.0268(14) Uani 1 1 d . . . H100 H 0.4280 0.3574 0.0232 0.032 Uiso 1 1 calc R . . N2 N 0.52576(13) 0.3098(6) -0.1243(4) 0.0231(13) Uani 1 1 d . . . H101 H 0.5278 0.3578 -0.1877 0.028 Uiso 1 1 calc R . . N3 N 0.62138(14) 0.0994(7) -0.0893(4) 0.0355(15) Uani 1 1 d . . . H102 H 0.6171 0.0729 -0.0217 0.043 Uiso 1 1 calc R . . O1 O 0.46061(10) 0.4919(5) -0.1854(3) 0.0253(11) Uani 1 1 d . . . O2 O 0.59311(10) 0.2253(5) -0.2340(3) 0.0336(12) Uani 1 1 d . . . Cl1 Cl 0.47040(4) 0.1935(2) 0.13794(11) 0.0291(5) Uani 1 1 d . . . Cl2 Cl 0.56313(4) 0.0363(2) 0.11321(11) 0.0294(5) Uani 1 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 0.023(4) 0.037(5) 0.040(4) -0.006(4) 0.015(3) 0.002(4) C2 0.032(4) 0.041(6) 0.051(5) 0.004(4) 0.005(4) 0.000(4) C3 0.037(4) 0.046(6) 0.033(4) -0.013(4) -0.002(4) -0.007(4) C4 0.029(4) 0.043(6) 0.041(4) -0.011(4) -0.003(3) 0.004(4) C5 0.028(4) 0.033(5) 0.037(4) -0.001(4) -0.017(3) 0.005(3) C6 0.018(3) 0.026(5) 0.031(4) -0.004(3) -0.006(3) -0.001(3) C7 0.024(4) 0.023(5) 0.027(4) 0.000(4) 0.004(3) -0.008(3) C8 0.015(3) 0.020(5) 0.020(4) -0.005(3) 0.001(3) -0.003(3) C9 0.030(4) 0.027(5) 0.014(4) 0.002(3) -0.002(3) -0.004(3) C10 0.028(4) 0.024(5) 0.020(4) -0.002(3) -0.002(3) 0.001(3) C11 0.030(4) 0.020(4) 0.023(4) -0.002(3) -0.003(3) -0.004(4) C12 0.024(4) 0.023(5) 0.023(4) 0.000(3) -0.003(3) -0.006(3) C13 0.019(3) 0.034(5) 0.040(4) -0.014(4) 0.001(3) -0.001(4) C14 0.030(4) 0.035(5) 0.033(4) -0.009(4) 0.005(3) -0.008(4) C15 0.021(4) 0.050(6) 0.044(4) -0.013(4) -0.001(3) -0.002(4) C16 0.033(4) 0.037(5) 0.043(5) -0.010(4) -0.011(4) -0.009(4) C17 0.034(4) 0.037(5) 0.054(5) -0.016(4) -0.007(4) 0.000(4) C18 0.028(4) 0.022(5) 0.055(4) -0.009(4) -0.021(4) 0.015(4) N1 0.029(3) 0.032(4) 0.019(3) 0.006(3) 0.000(3) 0.000(3) N2 0.022(3) 0.027(4) 0.020(3) 0.003(3) -0.003(3) 0.000(3) N3 0.027(3) 0.051(4) 0.028(3) 0.005(3) -0.003(3) 0.003(3) O1 0.025(2) 0.029(3) 0.023(2) 0.003(2) 0.003(2) 0.003(2) O2 0.033(3) 0.041(3) 0.027(3) 0.004(2) 0.003(2) 0.003(2) Cl1 0.0318(9) 0.0335(12) 0.0220(8) 0.0012(8) 0.0006(7) -0.0023(9) Cl2 0.0311(9) 0.0303(12) 0.0268(9) 0.0031(8) -0.0040(8) 0.0039(9) _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 1.385(8) . ? C1 C6 1.410(7) . ? C2 C3 1.410(9) . ? C3 C4 1.404(9) . ? C4 C5 1.414(8) . ? C5 C6 1.400(8) . ? C6 N1 1.414(6) . ? C7 O1 1.219(6) . ? C7 N1 1.356(7) . ? C7 C8 1.482(8) . ? C8 N2 1.351(6) . ? C8 C9 1.375(7) . ? C9 C10 1.410(7) . ? C9 Cl1 1.712(6) . ? C10 C11 1.386(7) . ? C10 Cl2 1.704(6) . ? C11 N2 1.368(7) . ? C11 C12 1.466(8) . ? C12 O2 1.225(6) . ? C12 N3 1.356(7) . ? C13 C18 1.396(8) . ? C13 C14 1.411(8) . ? C13 N3 1.420(7) . ? C14 C15 1.426(8) . ? C15 C16 1.386(8) . ? C16 C17 1.404(8) . ? C17 C18 1.428(8) . ? 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 C6 119.5(6) . . ? C1 C2 C3 120.3(6) . . ? C4 C3 C2 119.8(6) . . ? C3 C4 C5 120.6(6) . . ? C4 C5 C6 118.2(6) . . ? C5 C6 C1 121.6(5) . . ? C5 C6 N1 122.4(5) . . ? C1 C6 N1 116.0(5) . . ? O1 C7 N1 123.6(6) . . ? O1 C7 C8 120.7(5) . . ? N1 C7 C8 115.7(5) . . ? N2 C8 C9 107.3(5) . . ? N2 C8 C7 117.4(5) . . ? C9 C8 C7 135.4(5) . . ? C8 C9 C10 108.0(5) . . ? C8 C9 Cl1 127.2(5) . . ? C10 C9 Cl1 124.7(5) . . ? C11 C10 C9 106.9(5) . . ? C11 C10 Cl2 128.1(5) . . ? C9 C10 Cl2 125.0(5) . . ? N2 C11 C10 107.0(5) . . ? N2 C11 C12 117.9(5) . . ? C10 C11 C12 134.9(6) . . ? O2 C12 N3 123.0(5) . . ? O2 C12 C11 119.8(6) . . ? N3 C12 C11 117.3(5) . . ? C18 C13 C14 123.1(5) . . ? C18 C13 N3 115.4(6) . . ? C14 C13 N3 121.5(6) . . ? C13 C14 C15 116.9(6) . . ? C16 C15 C14 121.7(6) . . ? C15 C16 C17 119.9(6) . . ? C16 C17 C18 120.4(6) . . ? C13 C18 C17 117.9(6) . . ? C7 N1 C6 128.9(5) . . ? C8 N2 C11 110.8(5) . . ? C12 N3 C13 127.8(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H100 Cl1 0.88 2.40 3.176(5) 147.0 . N2 H101 O1 0.88 1.95 2.816(6) 169.2 3_654 N3 H102 Cl2 0.88 2.48 3.227(5) 142.4 . _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.629 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.101 data_s92_2 _database_code_CSD 178608 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H96 Cl4 N8 O4' _chemical_formula_weight 1231.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 13.2385(4) _cell_length_b 16.9228(5) _cell_length_c 15.0678(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.944(2) _cell_angle_gamma 90.00 _cell_volume 3324.96(17) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19094 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9773 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method ; \f and \w scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean '9.091 pixels mm^1^' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19094 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0981 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.03 _reflns_number_total 10094 _reflns_number_gt 7453 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; COLLECT (Hooft, 1998) ; _computing_cell_refinement ; SCALEPACK (Otwinoski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinoski and Minor, 1997), COLLECT (Hooft, 1998) MAXUS (Mackay et al., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(4) _refine_ls_number_reflns 10094 _refine_ls_number_parameters 766 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 C1 C 0.5584(3) 0.7204(2) 0.8172(2) 0.0283(10) Uani 1 1 d . . . H1 H 0.5821 0.6857 0.7756 0.034 Uiso 1 1 calc R . . C2 C 0.6223(3) 0.7400(2) 0.8973(3) 0.0343(10) Uani 1 1 d . . . H2 H 0.6903 0.7200 0.9092 0.041 Uiso 1 1 calc R . . C3 C 0.5885(3) 0.7880(2) 0.9597(3) 0.0324(10) Uani 1 1 d . . . H3 H 0.6321 0.8004 1.0148 0.039 Uiso 1 1 calc R . . C4 C 0.4909(3) 0.8178(2) 0.9411(2) 0.0304(10) Uani 1 1 d . . . H4 H 0.4672 0.8514 0.9836 0.036 Uiso 1 1 calc R . . C5 C 0.4266(3) 0.7998(2) 0.8615(2) 0.0256(9) Uani 1 1 d . . . H5 H 0.3590 0.8206 0.8500 0.031 Uiso 1 1 calc R . . C6 C 0.4604(3) 0.7513(2) 0.7979(2) 0.0241(9) Uani 1 1 d . . . C7 C 0.4162(3) 0.7099(2) 0.6365(2) 0.0223(9) Uani 1 1 d . . . C8 C 0.3246(3) 0.6968(2) 0.5673(2) 0.0205(9) Uani 1 1 d . . . C9 C 0.1614(3) 0.6916(2) 0.5102(2) 0.0204(9) Uani 1 1 d . . . C10 C 0.2146(3) 0.6759(2) 0.4400(2) 0.0222(9) Uani 1 1 d . . . C11 C 0.3186(3) 0.6799(2) 0.4761(2) 0.0208(9) Uani 1 1 d . . . C12 C 0.0507(3) 0.6955(2) 0.5090(2) 0.0207(9) Uani 1 1 d . . . C13 C -0.0733(3) 0.7263(2) 0.6134(2) 0.0238(9) Uani 1 1 d . . . C14 C -0.0773(3) 0.7635(2) 0.6952(3) 0.0306(10) Uani 1 1 d . . . H14 H -0.0159 0.7805 0.7326 0.037 Uiso 1 1 calc R . . C15 C -0.1714(3) 0.7755(2) 0.7216(3) 0.0359(10) Uani 1 1 d . . . H15 H -0.1743 0.8008 0.7774 0.043 Uiso 1 1 calc R . . C16 C -0.2609(3) 0.7513(2) 0.6676(3) 0.0362(11) Uani 1 1 d . . . H16 H -0.3253 0.7608 0.6851 0.043 Uiso 1 1 calc R . . C17 C -0.2555(3) 0.7130(2) 0.5879(3) 0.0330(10) Uani 1 1 d . . . H17 H -0.3170 0.6952 0.5513 0.040 Uiso 1 1 calc R . . C18 C -0.1617(3) 0.6996(2) 0.5595(3) 0.0261(9) Uani 1 1 d . . . H18 H -0.1590 0.6728 0.5046 0.031 Uiso 1 1 calc R . . C53 C 0.8669(3) 0.4658(2) 0.7210(2) 0.0235(9) Uani 1 1 d . . . H53A H 0.8102 0.4469 0.7506 0.028 Uiso 1 1 calc R . . H53B H 0.9292 0.4360 0.7472 0.028 Uiso 1 1 calc R . . C54 C 0.8850(3) 0.5524(2) 0.7433(2) 0.0263(9) Uani 1 1 d . . . H54A H 0.8297 0.5844 0.7078 0.032 Uiso 1 1 calc R . . H54B H 0.9511 0.5691 0.7269 0.032 Uiso 1 1 calc R . . C55 C 0.8872(3) 0.5667(2) 0.8438(2) 0.0293(10) Uani 1 1 d . . . H55A H 0.9354 0.5288 0.8788 0.035 Uiso 1 1 calc R . . H55B H 0.9135 0.6207 0.8593 0.035 Uiso 1 1 calc R . . C56 C 0.7832(3) 0.5581(2) 0.8713(3) 0.0355(10) Uani 1 1 d . . . H56A H 0.7334 0.5916 0.8329 0.053 Uiso 1 1 calc R . . H56B H 0.7876 0.5741 0.9344 0.053 Uiso 1 1 calc R . . H56C H 0.7611 0.5028 0.8645 0.053 Uiso 1 1 calc R . . C57 C 0.7453(3) 0.4901(2) 0.5774(2) 0.0209(9) Uani 1 1 d . . . H57A H 0.7266 0.4714 0.5144 0.025 Uiso 1 1 calc R . . H57B H 0.7625 0.5469 0.5751 0.025 Uiso 1 1 calc R . . C58 C 0.6516(3) 0.4822(2) 0.6223(2) 0.0281(10) Uani 1 1 d . . . H58A H 0.6418 0.4262 0.6379 0.034 Uiso 1 1 calc R . . H58B H 0.6613 0.5136 0.6786 0.034 Uiso 1 1 calc R . . C59 C 0.5589(3) 0.5114(2) 0.5589(2) 0.0323(10) Uani 1 1 d . . . H59A H 0.5522 0.4809 0.5022 0.039 Uiso 1 1 calc R . . H59B H 0.5701 0.5674 0.5442 0.039 Uiso 1 1 calc R . . C60 C 0.4597(3) 0.5052(2) 0.5950(3) 0.0310(10) Uani 1 1 d . . . H60A H 0.4479 0.4500 0.6100 0.046 Uiso 1 1 calc R . . H60B H 0.4030 0.5237 0.5492 0.046 Uiso 1 1 calc R . . H60C H 0.4640 0.5378 0.6493 0.046 Uiso 1 1 calc R . . C61 C 0.8170(3) 0.3583(2) 0.6112(2) 0.0233(9) Uani 1 1 d . . . H61A H 0.7649 0.3455 0.6489 0.028 Uiso 1 1 calc R . . H61B H 0.7855 0.3481 0.5478 0.028 Uiso 1 1 calc R . . C62 C 0.9057(3) 0.3023(2) 0.6360(3) 0.0325(10) Uani 1 1 d . . . H62A H 0.9412 0.3139 0.6980 0.039 Uiso 1 1 calc R . . H62B H 0.9553 0.3102 0.5946 0.039 Uiso 1 1 calc R . . C63 C 0.8695(3) 0.2174(2) 0.6306(3) 0.0319(10) Uani 1 1 d . . . H63A H 0.9302 0.1823 0.6401 0.038 Uiso 1 1 calc R . . H63B H 0.8313 0.2073 0.5691 0.038 Uiso 1 1 calc R . . C64 C 0.8006(4) 0.1956(2) 0.6990(3) 0.0410(11) Uani 1 1 d . . . H64A H 0.8326 0.2138 0.7591 0.061 Uiso 1 1 calc R . . H64B H 0.7918 0.1381 0.6998 0.061 Uiso 1 1 calc R . . H64C H 0.7336 0.2210 0.6818 0.061 Uiso 1 1 calc R . . C65 C 0.9280(3) 0.4701(2) 0.5751(2) 0.0240(9) Uani 1 1 d . . . H65A H 0.9901 0.4409 0.6033 0.029 Uiso 1 1 calc R . . H65B H 0.9417 0.5271 0.5865 0.029 Uiso 1 1 calc R . . C66 C 0.9122(3) 0.4563(2) 0.4741(2) 0.0300(10) Uani 1 1 d . . . H66A H 0.8920 0.4007 0.4610 0.036 Uiso 1 1 calc R . . H66B H 0.8558 0.4905 0.4440 0.036 Uiso 1 1 calc R . . C67 C 1.0089(3) 0.4742(2) 0.4369(2) 0.0291(10) Uani 1 1 d . . . H67A H 1.0596 0.4315 0.4542 0.035 Uiso 1 1 calc R . . H67B H 1.0392 0.5244 0.4628 0.035 Uiso 1 1 calc R . . C68 C 0.9847(3) 0.4810(2) 0.3343(2) 0.0345(10) Uani 1 1 d . . . H68A H 0.9497 0.4329 0.3090 0.052 Uiso 1 1 calc R . . H68B H 1.0486 0.4876 0.3106 0.052 Uiso 1 1 calc R . . H68C H 0.9402 0.5268 0.3174 0.052 Uiso 1 1 calc R . . N1 N 0.3922(2) 0.73402(17) 0.71770(18) 0.0232(7) Uani 1 1 d . . . H1A H 0.3265 0.7393 0.7197 0.028 Uiso 1 1 calc R . . N2 N 0.2288(2) 0.70454(16) 0.58764(18) 0.0198(7) Uani 1 1 d . . . N3 N 0.0264(2) 0.71747(16) 0.59057(19) 0.0212(7) Uani 1 1 d . . . H3A H 0.0785 0.7273 0.6339 0.025 Uiso 1 1 calc R . . N8 N 0.8407(2) 0.44614(16) 0.62115(18) 0.0210(7) Uani 1 1 d . . . O1 O 0.5042(2) 0.69959(15) 0.62373(16) 0.0302(7) Uani 1 1 d . . . O2 O -0.0134(2) 0.68166(14) 0.44229(16) 0.0273(6) Uani 1 1 d . . . Cl1 Cl 0.41730(7) 0.66837(6) 0.41544(6) 0.0305(2) Uani 1 1 d . . . Cl2 Cl 0.16460(8) 0.65831(5) 0.32786(6) 0.0297(2) Uani 1 1 d . . . C19 C 0.1557(3) 0.4836(2) 0.8058(2) 0.0262(9) Uani 1 1 d . . . H19 H 0.1337 0.4999 0.8597 0.031 Uiso 1 1 calc R . . C20 C 0.1589(3) 0.4046(2) 0.7860(3) 0.0360(11) Uani 1 1 d . . . H20 H 0.1408 0.3665 0.8269 0.043 Uiso 1 1 calc R . . C21 C 0.1886(3) 0.3799(2) 0.7060(3) 0.0337(10) Uani 1 1 d . . . H21 H 0.1900 0.3253 0.6917 0.040 Uiso 1 1 calc R . . C22 C 0.2159(3) 0.4357(2) 0.6478(3) 0.0293(10) Uani 1 1 d . . . H22 H 0.2362 0.4193 0.5932 0.035 Uiso 1 1 calc R . . C23 C 0.2142(3) 0.5146(2) 0.6680(3) 0.0271(9) Uani 1 1 d . . . H23 H 0.2336 0.5522 0.6274 0.033 Uiso 1 1 calc R . . C24 C 0.1844(3) 0.5402(2) 0.7477(2) 0.0234(9) Uani 1 1 d . . . C25 C 0.1663(3) 0.6607(2) 0.8390(2) 0.0248(9) Uani 1 1 d . . . C26 C 0.1636(3) 0.7470(2) 0.8308(2) 0.0233(9) Uani 1 1 d . . . C27 C 0.1679(3) 0.8631(2) 0.7675(2) 0.0227(9) Uani 1 1 d . . . C28 C 0.1421(3) 0.8755(2) 0.8521(2) 0.0268(9) Uani 1 1 d . . . C29 C 0.1401(3) 0.8029(2) 0.8923(2) 0.0253(9) Uani 1 1 d . . . C30 C 0.1835(3) 0.9215(2) 0.6991(2) 0.0253(9) Uani 1 1 d . . . C31 C 0.2467(3) 0.9330(2) 0.5531(2) 0.0228(9) Uani 1 1 d . . . C32 C 0.2867(3) 0.8891(2) 0.4897(2) 0.0331(11) Uani 1 1 d . . . H32 H 0.2872 0.8331 0.4938 0.040 Uiso 1 1 calc R . . C33 C 0.3259(4) 0.9251(2) 0.4207(3) 0.0430(12) Uani 1 1 d . . . H33 H 0.3534 0.8940 0.3782 0.052 Uiso 1 1 calc R . . C34 C 0.3249(4) 1.0057(2) 0.4139(3) 0.0406(12) Uani 1 1 d . . . H34 H 0.3521 1.0308 0.3667 0.049 Uiso 1 1 calc R . . C35 C 0.2845(3) 1.0501(2) 0.4753(3) 0.0373(11) Uani 1 1 d . . . H35 H 0.2830 1.1060 0.4699 0.045 Uiso 1 1 calc R . . C36 C 0.2459(3) 1.0146(2) 0.5452(3) 0.0322(10) Uani 1 1 d . . . H36 H 0.2188 1.0461 0.5877 0.039 Uiso 1 1 calc R . . N4 N 0.1826(2) 0.62218(17) 0.76231(19) 0.0247(8) Uani 1 1 d . . . H4A H 0.1932 0.6523 0.7172 0.030 Uiso 1 1 calc R . . N5 N 0.1801(2) 0.78412(16) 0.75426(18) 0.0217(7) Uani 1 1 d . . . N6 N 0.2125(2) 0.89134(17) 0.62256(19) 0.0274(8) Uani 1 1 d . . . H6 H 0.2092 0.8396 0.6165 0.033 Uiso 1 1 calc R . . O3 O 0.1548(2) 0.62647(15) 0.90791(16) 0.0335(7) Uani 1 1 d . . . O4 O 0.1712(2) 0.99286(16) 0.71015(17) 0.0380(7) Uani 1 1 d . . . Cl3 Cl 0.10948(9) 0.78736(6) 0.99745(6) 0.0417(3) Uani 1 1 d . . . Cl4 Cl 0.11754(9) 0.96402(6) 0.90210(7) 0.0434(3) Uani 1 1 d . . . C37 C 0.9860(4) 0.8963(2) 0.4256(3) 0.0416(12) Uani 1 1 d . . . H37A H 0.9764 0.8447 0.4539 0.050 Uiso 1 1 calc R . . H37B H 1.0598 0.9014 0.4227 0.050 Uiso 1 1 calc R . . C38 C 0.9584(4) 0.9606(3) 0.4868(3) 0.0577(15) Uani 1 1 d . . . H38A H 1.0203 0.9929 0.5072 0.069 Uiso 1 1 calc R . . H38B H 0.9067 0.9954 0.4509 0.069 Uiso 1 1 calc R . . C39 C 0.9196(5) 0.9354(3) 0.5634(3) 0.081(2) Uani 1 1 d . . . H39A H 0.9704 0.8990 0.5977 0.097 Uiso 1 1 calc R . . H39B H 0.8566 0.9044 0.5424 0.097 Uiso 1 1 calc R . . C40 C 0.8942(5) 0.9973(3) 0.6275(3) 0.0624(15) Uani 1 1 d . . . H40A H 0.9569 1.0254 0.6540 0.094 Uiso 1 1 calc R . . H40B H 0.8643 0.9719 0.6755 0.094 Uiso 1 1 calc R . . H40C H 0.8449 1.0348 0.5950 0.094 Uiso 1 1 calc R . . C41 C 0.8133(4) 0.8898(2) 0.3292(3) 0.0381(11) Uani 1 1 d . . . H41A H 0.7773 0.8972 0.2665 0.046 Uiso 1 1 calc R . . H41B H 0.7932 0.9339 0.3656 0.046 Uiso 1 1 calc R . . C42 C 0.7770(4) 0.8133(2) 0.3648(3) 0.0382(11) Uani 1 1 d . . . H42A H 0.8226 0.7992 0.4218 0.046 Uiso 1 1 calc R . . H42B H 0.7812 0.7705 0.3208 0.046 Uiso 1 1 calc R . . C43 C 0.6666(4) 0.8199(3) 0.3816(3) 0.0449(12) Uani 1 1 d . . . H43A H 0.6481 0.7705 0.4103 0.054 Uiso 1 1 calc R . . H43B H 0.6623 0.8638 0.4242 0.054 Uiso 1 1 calc R . . C44 C 0.5903(4) 0.8341(3) 0.2967(3) 0.0472(12) Uani 1 1 d . . . H44A H 0.6042 0.8853 0.2709 0.071 Uiso 1 1 calc R . . H44B H 0.5207 0.8342 0.3107 0.071 Uiso 1 1 calc R . . H44C H 0.5963 0.7921 0.2531 0.071 Uiso 1 1 calc R . . C45 C 0.9639(3) 0.8230(2) 0.2840(2) 0.0310(10) Uani 1 1 d . . . H45A H 1.0388 0.8281 0.2858 0.037 Uiso 1 1 calc R . . H45B H 0.9525 0.7753 0.3190 0.037 Uiso 1 1 calc R . . C46 C 0.9129(4) 0.8106(2) 0.1872(3) 0.0363(11) Uani 1 1 d . . . H46A H 0.9318 0.8545 0.1498 0.044 Uiso 1 1 calc R . . H46B H 0.8375 0.8115 0.1835 0.044 Uiso 1 1 calc R . . C47 C 0.9439(3) 0.7328(2) 0.1497(2) 0.0312(10) Uani 1 1 d . . . H47A H 1.0183 0.7338 0.1478 0.037 Uiso 1 1 calc R . . H47B H 0.9309 0.6892 0.1901 0.037 Uiso 1 1 calc R . . C48 C 0.8851(4) 0.7177(2) 0.0562(3) 0.0418(12) Uani 1 1 d . . . H48A H 0.8116 0.7149 0.0583 0.063 Uiso 1 1 calc R . . H48B H 0.9076 0.6675 0.0336 0.063 Uiso 1 1 calc R . . H48C H 0.8978 0.7607 0.0161 0.063 Uiso 1 1 calc R . . C49 C 0.9480(4) 0.9706(2) 0.2807(3) 0.0405(12) Uani 1 1 d . . . H49A H 0.9092 0.9679 0.2184 0.049 Uiso 1 1 calc R . . H49B H 0.9207 1.0158 0.3109 0.049 Uiso 1 1 calc R . . C50 C 1.0596(5) 0.9868(3) 0.2762(4) 0.0721(17) Uani 1 1 d . . . H50A H 1.0984 0.9919 0.3383 0.087 Uiso 1 1 calc R . . H50B H 1.0880 0.9410 0.2478 0.087 Uiso 1 1 calc R . . C51 C 1.0756(5) 1.0608(3) 0.2237(4) 0.0805(19) Uani 1 1 d . . . H51A H 1.0360 1.1046 0.2446 0.097 Uiso 1 1 calc R . . H51B H 1.1491 1.0755 0.2371 0.097 Uiso 1 1 calc R . . C52 C 1.0471(8) 1.0531(5) 0.1330(5) 0.158(4) Uani 1 1 d . . . H52A H 1.0546 0.9978 0.1159 0.236 Uiso 1 1 calc R . . H52B H 1.0907 1.0866 0.1024 0.236 Uiso 1 1 calc R . . H52C H 0.9754 1.0693 0.1154 0.236 Uiso 1 1 calc R . . N7 N 0.9272(3) 0.89456(17) 0.3302(2) 0.0322(9) Uani 1 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 0.027(3) 0.034(2) 0.023(2) -0.0041(18) 0.0011(19) -0.003(2) C2 0.025(3) 0.042(2) 0.034(2) -0.003(2) -0.003(2) 0.000(2) C3 0.032(3) 0.034(2) 0.027(2) -0.0080(19) -0.007(2) -0.004(2) C4 0.033(3) 0.034(2) 0.024(2) -0.0078(18) 0.0042(19) -0.004(2) C5 0.018(2) 0.032(2) 0.028(2) -0.0058(19) 0.0059(19) -0.0028(18) C6 0.018(3) 0.028(2) 0.026(2) 0.0050(18) 0.0050(19) -0.0064(19) C7 0.023(3) 0.019(2) 0.024(2) 0.0009(17) 0.0002(19) 0.0003(18) C8 0.020(2) 0.020(2) 0.0202(19) 0.0010(16) 0.0012(17) -0.0024(17) C9 0.021(2) 0.020(2) 0.0196(19) 0.0001(16) 0.0025(17) 0.0018(17) C10 0.026(3) 0.020(2) 0.0198(19) -0.0031(17) 0.0017(17) 0.0026(18) C11 0.019(2) 0.027(2) 0.0182(19) 0.0008(17) 0.0084(17) 0.0013(17) C12 0.021(3) 0.017(2) 0.022(2) 0.0032(17) -0.0004(19) -0.0019(18) C13 0.016(2) 0.025(2) 0.031(2) 0.0053(19) 0.0067(19) -0.0002(18) C14 0.020(3) 0.040(2) 0.033(2) 0.001(2) 0.0065(19) -0.003(2) C15 0.030(3) 0.048(3) 0.032(2) -0.003(2) 0.009(2) 0.002(2) C16 0.023(3) 0.044(3) 0.044(3) 0.007(2) 0.014(2) 0.006(2) C17 0.016(3) 0.042(3) 0.041(3) 0.012(2) 0.004(2) -0.004(2) C18 0.020(3) 0.027(2) 0.031(2) 0.0069(18) 0.0017(19) 0.0014(19) C53 0.022(2) 0.028(2) 0.0182(19) 0.0046(17) -0.0008(17) 0.0025(18) C54 0.025(3) 0.031(2) 0.021(2) 0.0008(18) 0.0002(17) -0.0028(19) C55 0.028(3) 0.034(2) 0.023(2) -0.0006(19) -0.0026(18) 0.0018(19) C56 0.033(3) 0.045(3) 0.030(2) -0.009(2) 0.0088(19) 0.004(2) C57 0.017(2) 0.025(2) 0.0198(19) -0.0029(17) 0.0000(17) -0.0011(17) C58 0.024(3) 0.035(2) 0.025(2) 0.0040(18) 0.0035(18) 0.0059(19) C59 0.023(3) 0.052(3) 0.022(2) 0.002(2) 0.0039(18) 0.003(2) C60 0.022(3) 0.034(2) 0.037(2) 0.000(2) 0.0039(19) 0.0058(19) C61 0.026(3) 0.022(2) 0.0226(19) -0.0044(17) 0.0053(17) -0.0021(18) C62 0.032(3) 0.030(2) 0.036(2) -0.0010(19) 0.008(2) 0.003(2) C63 0.035(3) 0.030(2) 0.031(2) -0.0001(19) 0.006(2) 0.0068(19) C64 0.057(3) 0.031(2) 0.038(2) -0.001(2) 0.018(2) -0.001(2) C65 0.021(2) 0.028(2) 0.025(2) 0.0036(18) 0.0079(17) -0.0025(18) C66 0.024(3) 0.041(3) 0.026(2) -0.001(2) 0.0068(18) -0.001(2) C67 0.028(3) 0.033(2) 0.028(2) -0.0026(18) 0.0103(19) 0.0018(19) C68 0.035(3) 0.042(2) 0.027(2) 0.0023(19) 0.0085(19) -0.002(2) N1 0.0120(19) 0.0377(19) 0.0196(17) -0.0034(15) 0.0021(14) -0.0021(15) N2 0.017(2) 0.0231(17) 0.0196(16) -0.0012(14) 0.0043(14) 0.0016(14) N3 0.0097(18) 0.0334(18) 0.0203(16) 0.0002(14) 0.0016(13) -0.0011(14) N8 0.021(2) 0.0228(17) 0.0186(15) -0.0016(14) 0.0033(14) -0.0010(14) O1 0.0160(18) 0.0445(17) 0.0311(15) -0.0042(13) 0.0067(13) -0.0013(13) O2 0.0198(16) 0.0365(16) 0.0241(14) -0.0018(12) -0.0009(13) 0.0017(13) Cl1 0.0242(6) 0.0448(6) 0.0244(5) -0.0010(5) 0.0093(4) 0.0052(5) Cl2 0.0282(6) 0.0407(6) 0.0193(5) -0.0020(5) 0.0018(4) 0.0037(5) C19 0.024(3) 0.028(2) 0.027(2) 0.0044(18) 0.0077(18) -0.0027(18) C20 0.033(3) 0.039(3) 0.038(2) 0.015(2) 0.009(2) -0.002(2) C21 0.029(3) 0.026(2) 0.046(3) 0.001(2) 0.006(2) -0.0015(19) C22 0.025(3) 0.032(3) 0.030(2) 0.000(2) 0.0025(19) -0.0006(19) C23 0.020(3) 0.030(2) 0.032(2) 0.0036(19) 0.0066(18) -0.0009(18) C24 0.008(2) 0.031(2) 0.030(2) 0.0035(19) -0.0014(17) 0.0031(17) C25 0.014(2) 0.041(2) 0.019(2) 0.004(2) 0.0000(16) 0.000(2) C26 0.017(2) 0.032(2) 0.0192(19) 0.0002(19) 0.0002(16) -0.0005(19) C27 0.021(2) 0.028(2) 0.0196(19) -0.0032(18) 0.0041(17) -0.0065(18) C28 0.018(2) 0.031(2) 0.031(2) -0.0091(19) 0.0034(18) -0.0032(19) C29 0.019(2) 0.042(3) 0.0157(19) 0.0005(19) 0.0046(17) -0.0019(19) C30 0.019(2) 0.027(2) 0.031(2) -0.0022(19) 0.0050(18) -0.0050(18) C31 0.018(2) 0.023(2) 0.026(2) -0.0038(18) 0.0006(17) -0.0032(18) C32 0.050(3) 0.024(2) 0.027(2) -0.0005(19) 0.014(2) -0.001(2) C33 0.066(4) 0.034(3) 0.034(2) -0.003(2) 0.021(2) 0.000(2) C34 0.051(3) 0.036(3) 0.038(2) 0.005(2) 0.018(2) -0.009(2) C35 0.051(3) 0.026(2) 0.035(2) 0.000(2) 0.007(2) -0.002(2) C36 0.039(3) 0.031(2) 0.030(2) -0.007(2) 0.014(2) -0.002(2) N4 0.026(2) 0.0250(18) 0.0227(17) 0.0052(15) 0.0041(15) -0.0023(15) N5 0.017(2) 0.0250(18) 0.0227(17) -0.0017(15) 0.0032(14) -0.0010(15) N6 0.037(2) 0.0192(17) 0.0289(18) -0.0054(15) 0.0153(16) -0.0046(15) O3 0.041(2) 0.0384(16) 0.0225(14) 0.0073(13) 0.0083(13) 0.0071(14) O4 0.054(2) 0.0288(17) 0.0356(16) -0.0105(13) 0.0200(15) -0.0090(14) Cl3 0.0461(8) 0.0576(7) 0.0253(5) 0.0013(5) 0.0172(5) 0.0069(6) Cl4 0.0574(8) 0.0371(6) 0.0415(6) -0.0118(5) 0.0247(6) -0.0002(6) C37 0.057(3) 0.035(3) 0.034(2) -0.003(2) 0.010(2) 0.004(2) C38 0.096(5) 0.041(3) 0.036(3) -0.001(2) 0.011(3) 0.016(3) C39 0.148(6) 0.050(3) 0.054(3) 0.001(3) 0.047(4) 0.029(4) C40 0.096(5) 0.046(3) 0.053(3) -0.014(3) 0.036(3) -0.004(3) C41 0.046(3) 0.028(2) 0.043(3) 0.008(2) 0.015(2) 0.010(2) C42 0.041(3) 0.038(3) 0.034(2) 0.004(2) 0.000(2) 0.004(2) C43 0.057(4) 0.034(3) 0.044(3) 0.008(2) 0.011(2) 0.000(2) C44 0.048(3) 0.045(3) 0.048(3) 0.003(2) 0.004(2) 0.002(2) C45 0.034(3) 0.027(2) 0.031(2) -0.0035(19) 0.0040(19) 0.006(2) C46 0.043(3) 0.037(3) 0.029(2) 0.002(2) 0.004(2) 0.001(2) C47 0.033(3) 0.032(2) 0.029(2) -0.0027(19) 0.0050(19) -0.0057(19) C48 0.051(3) 0.044(3) 0.028(2) 0.003(2) -0.003(2) -0.003(2) C49 0.058(4) 0.023(2) 0.044(3) 0.005(2) 0.020(2) 0.001(2) C50 0.082(5) 0.067(4) 0.074(4) 0.028(3) 0.033(3) -0.016(3) C51 0.110(6) 0.049(3) 0.096(5) -0.009(3) 0.056(4) -0.011(3) C52 0.207(10) 0.161(8) 0.080(5) 0.052(6) -0.042(6) -0.064(7) N7 0.043(3) 0.0252(19) 0.0284(18) 0.0047(15) 0.0062(17) 0.0052(17) _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 C6 1.383(5) . ? C1 C2 1.390(5) . ? C2 C3 1.374(5) . ? C3 C4 1.370(5) . ? C4 C5 1.379(5) . ? C5 C6 1.394(5) . ? C6 N1 1.409(4) . ? C7 O1 1.226(4) . ? C7 N1 1.378(4) . ? C7 C8 1.473(5) . ? C8 N2 1.361(4) . ? C8 C11 1.393(5) . ? C9 N2 1.358(4) . ? C9 C10 1.393(5) . ? C9 C12 1.465(5) . ? C10 C11 1.392(5) . ? C10 Cl2 1.731(4) . ? C11 Cl1 1.729(4) . ? C12 O2 1.221(4) . ? C12 N3 1.374(4) . ? C13 C18 1.381(5) . ? C13 C14 1.394(5) . ? C13 N3 1.428(4) . ? C14 C15 1.387(5) . ? C15 C16 1.379(6) . ? C16 C17 1.376(5) . ? C17 C18 1.400(5) . ? C53 C54 1.513(5) . ? C53 N8 1.521(4) . ? C54 C55 1.529(5) . ? C55 C56 1.512(5) . ? C57 N8 1.516(4) . ? C57 C58 1.519(5) . ? C58 C59 1.502(5) . ? C59 C60 1.509(5) . ? C61 C62 1.505(5) . ? C61 N8 1.521(4) . ? C62 C63 1.513(5) . ? C63 C64 1.534(5) . ? C65 N8 1.504(4) . ? C65 C66 1.518(5) . ? C66 C67 1.515(5) . ? C67 C68 1.528(5) . ? C19 C20 1.373(5) . ? C19 C24 1.395(5) . ? C20 C21 1.395(5) . ? C21 C22 1.378(5) . ? C22 C23 1.370(5) . ? C23 C24 1.396(5) . ? C24 N4 1.405(4) . ? C25 O3 1.222(4) . ? C25 N4 1.376(4) . ? C25 C26 1.466(5) . ? C26 N5 1.363(4) . ? C26 C29 1.396(5) . ? C27 N5 1.366(4) . ? C27 C28 1.392(5) . ? C27 C30 1.467(5) . ? C28 C29 1.371(5) . ? C28 Cl4 1.733(4) . ? C29 Cl3 1.723(3) . ? C30 O4 1.234(4) . ? C30 N6 1.375(4) . ? C31 C32 1.385(5) . ? C31 C36 1.385(5) . ? C31 N6 1.401(4) . ? C32 C33 1.381(5) . ? C33 C34 1.367(6) . ? C34 C35 1.371(6) . ? C35 C36 1.385(5) . ? C37 C38 1.511(5) . ? C37 N7 1.512(5) . ? C38 C39 1.407(6) . ? C39 C40 1.502(6) . ? C41 N7 1.508(5) . ? C41 C42 1.511(5) . ? C42 C43 1.530(6) . ? C43 C44 1.507(6) . ? C45 C46 1.513(5) . ? C45 N7 1.518(4) . ? C46 C47 1.516(5) . ? C47 C48 1.509(5) . ? C49 C50 1.517(7) . ? C49 N7 1.535(5) . ? C50 C51 1.516(7) . ? C51 C52 1.360(8) . ? 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 C6 C1 C2 120.0(4) . . ? C3 C2 C1 121.0(4) . . ? C4 C3 C2 119.0(4) . . ? C3 C4 C5 121.0(4) . . ? C4 C5 C6 120.3(4) . . ? C1 C6 C5 118.7(3) . . ? C1 C6 N1 122.8(3) . . ? C5 C6 N1 118.5(3) . . ? O1 C7 N1 123.6(3) . . ? O1 C7 C8 123.8(3) . . ? N1 C7 C8 112.6(3) . . ? N2 C8 C11 110.2(3) . . ? N2 C8 C7 120.8(3) . . ? C11 C8 C7 128.9(4) . . ? N2 C9 C10 109.9(3) . . ? N2 C9 C12 120.7(3) . . ? C10 C9 C12 129.5(3) . . ? C11 C10 C9 106.9(3) . . ? C11 C10 Cl2 125.1(3) . . ? C9 C10 Cl2 128.0(3) . . ? C10 C11 C8 106.2(3) . . ? C10 C11 Cl1 125.1(3) . . ? C8 C11 Cl1 128.7(3) . . ? O2 C12 N3 123.5(3) . . ? O2 C12 C9 123.6(3) . . ? N3 C12 C9 112.9(3) . . ? C18 C13 C14 120.7(4) . . ? C18 C13 N3 123.3(3) . . ? C14 C13 N3 116.0(3) . . ? C15 C14 C13 119.6(4) . . ? C16 C15 C14 120.6(4) . . ? C17 C16 C15 119.1(4) . . ? C16 C17 C18 121.7(4) . . ? C13 C18 C17 118.3(4) . . ? C54 C53 N8 115.6(3) . . ? C53 C54 C55 110.4(3) . . ? C56 C55 C54 113.2(3) . . ? N8 C57 C58 116.5(3) . . ? C59 C58 C57 109.1(3) . . ? C58 C59 C60 114.4(3) . . ? C62 C61 N8 116.9(3) . . ? C61 C62 C63 111.0(3) . . ? C62 C63 C64 114.3(3) . . ? N8 C65 C66 115.9(3) . . ? C67 C66 C65 111.2(3) . . ? C66 C67 C68 110.3(3) . . ? C7 N1 C6 127.7(3) . . ? C9 N2 C8 106.8(3) . . ? C12 N3 C13 127.7(3) . . ? C65 N8 C57 108.4(3) . . ? C65 N8 C61 112.4(3) . . ? C57 N8 C61 107.1(3) . . ? C65 N8 C53 109.6(3) . . ? C57 N8 C53 110.7(3) . . ? C61 N8 C53 108.6(3) . . ? C20 C19 C24 120.7(4) . . ? C19 C20 C21 120.3(4) . . ? C22 C21 C20 119.2(4) . . ? C23 C22 C21 120.7(4) . . ? C22 C23 C24 120.8(4) . . ? C19 C24 C23 118.3(3) . . ? C19 C24 N4 124.5(3) . . ? C23 C24 N4 117.2(3) . . ? O3 C25 N4 123.3(3) . . ? O3 C25 C26 122.6(3) . . ? N4 C25 C26 114.0(3) . . ? N5 C26 C29 109.7(3) . . ? N5 C26 C25 121.7(3) . . ? C29 C26 C25 128.6(3) . . ? N5 C27 C28 109.6(3) . . ? N5 C27 C30 121.5(3) . . ? C28 C27 C30 129.0(3) . . ? C29 C28 C27 107.2(3) . . ? C29 C28 Cl4 124.3(3) . . ? C27 C28 Cl4 128.5(3) . . ? C28 C29 C26 106.9(3) . . ? C28 C29 Cl3 124.7(3) . . ? C26 C29 Cl3 128.4(3) . . ? O4 C30 N6 122.6(3) . . ? O4 C30 C27 121.7(3) . . ? N6 C30 C27 115.7(3) . . ? C32 C31 C36 118.3(3) . . ? C32 C31 N6 117.1(3) . . ? C36 C31 N6 124.5(3) . . ? C33 C32 C31 121.3(4) . . ? C34 C33 C32 119.8(4) . . ? C33 C34 C35 119.7(4) . . ? C34 C35 C36 120.9(4) . . ? C35 C36 C31 119.9(4) . . ? C25 N4 C24 127.5(3) . . ? C26 N5 C27 106.7(3) . . ? C30 N6 C31 127.8(3) . . ? C38 C37 N7 117.1(4) . . ? C39 C38 C37 116.3(4) . . ? C38 C39 C40 118.1(4) . . ? N7 C41 C42 114.9(3) . . ? C41 C42 C43 111.6(3) . . ? C44 C43 C42 113.0(4) . . ? C46 C45 N7 115.4(3) . . ? C45 C46 C47 112.0(3) . . ? C48 C47 C46 111.5(3) . . ? C50 C49 N7 115.5(4) . . ? C51 C50 C49 113.5(5) . . ? C52 C51 C50 113.9(5) . . ? C41 N7 C37 111.1(3) . . ? C41 N7 C45 110.6(3) . . ? C37 N7 C45 107.4(3) . . ? C41 N7 C49 107.6(3) . . ? C37 N7 C49 109.8(3) . . ? C45 N7 C49 110.3(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N5 0.88 2.22 3.072(4) 161.5 . N3 H3A N5 0.88 2.28 3.124(4) 161.9 . N4 H4A N2 0.88 2.27 3.130(4) 167.4 . N6 H6 N2 0.88 2.35 3.218(4) 168.9 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.325 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051