# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal SOciety of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'David Dolphin' _publ_contact_author_email DAVID.DOLPHIN@QLTINC.COM _publ_section_title ; Conformational Flexibility of Dipyrromethenes: Supramolecular Assemblies with Hydroquinones ; loop_ _publ_author_name 'D Dolphin' "Brian O'Patrick" 'Ji-Young Shin.' # Attachment 'CIFs.txt' data_Compound1 _database_code_depnum_ccdc_archive 'CCDC 673445' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N3 O2' _chemical_formula_weight 265.27 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.6809(16) _cell_length_b 7.4146(9) _cell_length_c 24.350(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2650.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6096 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 23.97 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54647 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3122 _reflns_number_gt 2243 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0512P)^2^+0.5503P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3122 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34074(10) 0.2034(2) 0.13516(6) 0.0519(4) Uani 1 1 d . . . H1 H 0.3071 0.0973 0.1434 0.062 Uiso 1 1 calc R . . C2 C 0.31679(11) 0.3320(2) 0.09683(6) 0.0536(4) Uani 1 1 d . . . H2 H 0.2641 0.3302 0.0742 0.064 Uiso 1 1 calc R . . C3 C 0.38429(10) 0.4659(2) 0.09730(5) 0.0477(3) Uani 1 1 d . . . H3 H 0.3855 0.5715 0.0752 0.057 Uiso 1 1 calc R . . C4 C 0.44968(9) 0.41526(17) 0.13644(5) 0.0391(3) Uani 1 1 d . . . C5 C 0.53293(9) 0.50252(16) 0.15289(5) 0.0368(3) Uani 1 1 d . . . C6 C 0.58779(9) 0.44213(17) 0.19552(5) 0.0380(3) Uani 1 1 d . . . C7 C 0.67783(10) 0.50415(18) 0.21050(5) 0.0435(3) Uani 1 1 d . . . H7 H 0.7109 0.5998 0.1939 0.052 Uiso 1 1 calc R . . C8 C 0.70580(10) 0.3988(2) 0.25291(6) 0.0498(4) Uani 1 1 d . . . H8 H 0.7624 0.4057 0.2717 0.060 Uiso 1 1 calc R . . C9 C 0.63284(11) 0.2748(2) 0.26370(5) 0.0504(4) Uani 1 1 d . . . H9 H 0.6346 0.1865 0.2920 0.060 Uiso 1 1 calc R . . C10 C 0.56087(9) 0.66819(17) 0.12200(5) 0.0378(3) Uani 1 1 d . . . C11 C 0.57832(9) 0.82897(17) 0.15038(5) 0.0427(3) Uani 1 1 d . . . H11 H 0.5713 0.8324 0.1891 0.051 Uiso 1 1 calc R . . C12 C 0.60580(10) 0.98379(18) 0.12253(6) 0.0496(4) Uani 1 1 d . . . H12 H 0.6188 1.0921 0.1418 0.059 Uiso 1 1 calc R . . C13 C 0.61371(10) 0.9754(2) 0.06582(6) 0.0516(4) Uani 1 1 d . . . C14 C 0.59651(11) 0.8195(2) 0.03618(6) 0.0537(4) Uani 1 1 d . . . H14 H 0.6025 0.8182 -0.0027 0.064 Uiso 1 1 calc R . . C15 C 0.57040(10) 0.6653(2) 0.06443(5) 0.0465(3) Uani 1 1 d . . . H15 H 0.5589 0.5569 0.0448 0.056 Uiso 1 1 calc R . . N1 N 0.42022(8) 0.25340(16) 0.15914(5) 0.0448(3) Uani 1 1 d . . . N2 N 0.56307(8) 0.29641(15) 0.23023(4) 0.0451(3) Uani 1 1 d . . . N3 N 0.64200(11) 1.1402(2) 0.03623(8) 0.0759(5) Uani 1 1 d . . . O1 O 0.67250(13) 1.2687(2) 0.06305(8) 0.1067(6) Uani 1 1 d . . . O2 O 0.63308(11) 1.1408(2) -0.01446(7) 0.1018(6) Uani 1 1 d . . . H1N H 0.4498(12) 0.199(2) 0.1880(7) 0.068(5) Uiso 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 0.0512(9) 0.0560(9) 0.0487(8) -0.0098(7) 0.0094(7) -0.0098(7) C2 0.0483(9) 0.0700(10) 0.0427(7) -0.0112(7) 0.0007(6) -0.0032(8) C3 0.0523(9) 0.0528(8) 0.0381(7) -0.0023(6) 0.0015(6) 0.0029(7) C4 0.0460(7) 0.0370(7) 0.0342(6) -0.0035(5) 0.0059(5) 0.0030(6) C5 0.0460(7) 0.0325(6) 0.0319(6) -0.0025(5) 0.0073(5) 0.0047(5) C6 0.0455(7) 0.0357(6) 0.0327(6) -0.0005(5) 0.0061(5) 0.0027(6) C7 0.0488(8) 0.0399(7) 0.0417(7) -0.0002(6) 0.0041(6) 0.0021(6) C8 0.0514(8) 0.0529(8) 0.0451(7) 0.0013(7) -0.0037(6) 0.0071(7) C9 0.0622(10) 0.0497(8) 0.0391(7) 0.0096(6) 0.0034(6) 0.0092(7) C10 0.0399(7) 0.0376(7) 0.0358(6) 0.0025(5) 0.0048(5) 0.0050(5) C11 0.0475(8) 0.0379(7) 0.0427(7) 0.0004(6) 0.0089(6) 0.0047(6) C12 0.0478(8) 0.0363(7) 0.0646(9) 0.0012(6) 0.0156(7) 0.0058(6) C13 0.0460(8) 0.0438(8) 0.0651(9) 0.0186(7) 0.0213(7) 0.0120(6) C14 0.0578(9) 0.0615(10) 0.0417(7) 0.0140(7) 0.0148(6) 0.0127(7) C15 0.0562(9) 0.0458(8) 0.0374(7) 0.0011(6) 0.0060(6) 0.0059(7) N1 0.0477(7) 0.0415(6) 0.0450(6) -0.0006(5) 0.0062(5) -0.0019(5) N2 0.0551(7) 0.0431(6) 0.0371(5) 0.0065(5) 0.0064(5) 0.0023(5) N3 0.0682(10) 0.0576(10) 0.1019(12) 0.0356(9) 0.0420(9) 0.0169(8) O1 0.1271(14) 0.0459(7) 0.1471(15) 0.0178(9) 0.0620(11) -0.0047(8) O2 0.0964(11) 0.1070(12) 0.1021(11) 0.0655(10) 0.0316(8) 0.0100(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 N1 1.357(2) . ? C1 C2 1.380(2) . ? C1 H1 0.9500 . ? C2 C3 1.403(2) . ? C2 H2 0.9500 . ? C3 C4 1.4039(19) . ? C3 H3 0.9500 . ? C4 N1 1.3903(17) . ? C4 C5 1.4397(19) . ? C5 C6 1.3882(18) . ? C5 C10 1.4977(17) . ? C6 N2 1.4190(16) . ? C6 C7 1.446(2) . ? C7 C8 1.3585(19) . ? C7 H7 0.9500 . ? C8 C9 1.436(2) . ? C8 H8 0.9500 . ? C9 N2 1.3186(19) . ? C9 H9 0.9500 . ? C10 C11 1.4015(18) . ? C10 C15 1.4090(18) . ? C11 C12 1.3930(18) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.386(2) . ? C13 N3 1.4781(19) . ? C14 C15 1.389(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? N1 H1N 0.920(18) . ? N3 O1 1.239(2) . ? N3 O2 1.241(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.74(13) . . ? N1 C1 H1 125.6 . . ? C2 C1 H1 125.6 . . ? C1 C2 C3 107.68(13) . . ? C1 C2 H2 126.2 . . ? C3 C2 H2 126.2 . . ? C2 C3 C4 107.41(13) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C3 106.75(12) . . ? N1 C4 C5 122.78(12) . . ? C3 C4 C5 130.47(12) . . ? C6 C5 C4 123.76(12) . . ? C6 C5 C10 118.76(12) . . ? C4 C5 C10 117.48(11) . . ? C5 C6 N2 122.86(12) . . ? C5 C6 C7 128.05(12) . . ? N2 C6 C7 109.01(11) . . ? C8 C7 C6 106.56(12) . . ? C8 C7 H7 126.7 . . ? C6 C7 H7 126.7 . . ? C7 C8 C9 106.37(13) . . ? C7 C8 H8 126.8 . . ? C9 C8 H8 126.8 . . ? N2 C9 C8 112.86(12) . . ? N2 C9 H9 123.6 . . ? C8 C9 H9 123.6 . . ? C11 C10 C15 119.05(12) . . ? C11 C10 C5 120.01(10) . . ? C15 C10 C5 120.95(12) . . ? C12 C11 C10 120.92(12) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 118.16(13) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C14 C13 C12 122.73(13) . . ? C14 C13 N3 119.12(14) . . ? C12 C13 N3 118.15(15) . . ? C13 C14 C15 118.63(13) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C14 C15 C10 120.50(13) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C1 N1 C4 109.41(12) . . ? C1 N1 H1N 127.8(11) . . ? C4 N1 H1N 122.6(11) . . ? C9 N2 C6 105.19(12) . . ? O1 N3 O2 124.02(16) . . ? O1 N3 C13 118.70(17) . . ? O2 N3 C13 117.28(19) . . ? 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 N1 C1 C2 C3 0.07(16) . . . . ? C1 C2 C3 C4 0.30(16) . . . . ? C2 C3 C4 N1 -0.55(15) . . . . ? C2 C3 C4 C5 179.24(13) . . . . ? N1 C4 C5 C6 -5.23(19) . . . . ? C3 C4 C5 C6 175.02(13) . . . . ? N1 C4 C5 C10 175.02(11) . . . . ? C3 C4 C5 C10 -4.73(19) . . . . ? C4 C5 C6 N2 -5.49(19) . . . . ? C10 C5 C6 N2 174.25(10) . . . . ? C4 C5 C6 C7 170.87(12) . . . . ? C10 C5 C6 C7 -9.38(19) . . . . ? C5 C6 C7 C8 -176.88(13) . . . . ? N2 C6 C7 C8 -0.11(14) . . . . ? C6 C7 C8 C9 -0.39(15) . . . . ? C7 C8 C9 N2 0.82(17) . . . . ? C6 C5 C10 C11 -54.47(17) . . . . ? C4 C5 C10 C11 125.29(13) . . . . ? C6 C5 C10 C15 125.26(13) . . . . ? C4 C5 C10 C15 -54.98(16) . . . . ? C15 C10 C11 C12 -0.8(2) . . . . ? C5 C10 C11 C12 178.96(12) . . . . ? C10 C11 C12 C13 1.2(2) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C11 C12 C13 N3 179.42(13) . . . . ? C12 C13 C14 C15 -0.1(2) . . . . ? N3 C13 C14 C15 179.69(14) . . . . ? C13 C14 C15 C10 0.6(2) . . . . ? C11 C10 C15 C14 -0.2(2) . . . . ? C5 C10 C15 C14 -179.88(13) . . . . ? C2 C1 N1 C4 -0.42(15) . . . . ? C3 C4 N1 C1 0.60(14) . . . . ? C5 C4 N1 C1 -179.20(12) . . . . ? C8 C9 N2 C6 -0.86(16) . . . . ? C5 C6 N2 C9 177.57(12) . . . . ? C7 C6 N2 C9 0.59(14) . . . . ? C14 C13 N3 O1 -167.49(16) . . . . ? C12 C13 N3 O1 12.3(2) . . . . ? C14 C13 N3 O2 12.8(2) . . . . ? C12 C13 N3 O2 -167.37(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.214 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.032 #===End data_compound2 _database_code_depnum_ccdc_archive 'CCDC 673446' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H13 Cl2 N5 O4' _chemical_formula_weight 494.28 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 'P 21/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 10.508(2) _cell_length_b 19.587(3) _cell_length_c 11.039(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.970(10) _cell_angle_gamma 90.00 _cell_volume 2161.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4965 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 22.98 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34997 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.15 _reflns_number_total 3842 _reflns_number_gt 2752 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0702P)^2^+0.4140P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3842 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9359(3) 0.08992(13) 0.5275(2) 0.0226(6) Uani 1 1 d . . . C2 C 0.9642(3) 0.06700(13) 0.6539(2) 0.0241(6) Uani 1 1 d . . . C3 C 0.8954(3) 0.01659(14) 0.7017(3) 0.0280(6) Uani 1 1 d . . . H3 H 0.8162 -0.0064 0.6542 0.034 Uiso 1 1 calc R . . C4 C 0.9635(3) 0.00661(16) 0.8292(3) 0.0358(7) Uani 1 1 d . . . H4 H 0.9409 -0.0248 0.8849 0.043 Uiso 1 1 calc R . . C5 C 1.0714(3) 0.05141(16) 0.8602(3) 0.0343(7) Uani 1 1 d . . . H5 H 1.1346 0.0561 0.9425 0.041 Uiso 1 1 calc R . . C6 C 1.0299(3) 0.12280(13) 0.4789(2) 0.0238(6) Uani 1 1 d . . . C7 C 1.1704(3) 0.12706(13) 0.5249(3) 0.0263(6) Uani 1 1 d . . . H7 H 1.2258 0.1093 0.6036 0.032 Uiso 1 1 calc R . . C8 C 1.2137(3) 0.16152(15) 0.4357(3) 0.0342(7) Uani 1 1 d . . . H8 H 1.3039 0.1715 0.4417 0.041 Uiso 1 1 calc R . . C9 C 1.1009(3) 0.17892(14) 0.3355(3) 0.0351(7) Uani 1 1 d . . . H9 H 1.1012 0.2032 0.2611 0.042 Uiso 1 1 calc R . . C10 C 0.7995(3) 0.07586(13) 0.4401(2) 0.0234(6) Uani 1 1 d . . . C11 C 0.7820(3) 0.04906(13) 0.3180(2) 0.0247(6) Uani 1 1 d . . . H11 H 0.8583 0.0393 0.2921 0.030 Uiso 1 1 calc R . . C12 C 0.6558(3) 0.03677(14) 0.2352(3) 0.0279(6) Uani 1 1 d . . . H12 H 0.6439 0.0181 0.1530 0.034 Uiso 1 1 calc R . . C13 C 0.5469(3) 0.05257(14) 0.2759(3) 0.0278(6) Uani 1 1 d . . . C14 C 0.5599(3) 0.07817(14) 0.3958(3) 0.0315(7) Uani 1 1 d . . . H14 H 0.4832 0.0877 0.4211 0.038 Uiso 1 1 calc R . . C15 C 0.6869(3) 0.08959(14) 0.4780(3) 0.0300(7) Uani 1 1 d . . . H15 H 0.6977 0.1069 0.5609 0.036 Uiso 1 1 calc R . . C16 C 0.4899(3) 0.21268(14) 1.1351(2) 0.0283(7) Uani 1 1 d . . . C17 C 0.6192(3) 0.19838(13) 1.1296(3) 0.0287(7) Uani 1 1 d . . . C18 C 0.6314(3) 0.17126(13) 1.0165(3) 0.0277(6) Uani 1 1 d . . . C19 C 0.5172(3) 0.16100(13) 0.9093(3) 0.0262(6) Uani 1 1 d . . . C20 C 0.3879(3) 0.17761(13) 0.9130(2) 0.0258(6) Uani 1 1 d . . . C21 C 0.3776(3) 0.20157(13) 1.0303(3) 0.0270(6) Uani 1 1 d . . . C22 C 0.7657(3) 0.15692(16) 1.0098(3) 0.0361(7) Uani 1 1 d . . . C23 C 0.5298(3) 0.13652(15) 0.7889(3) 0.0319(7) Uani 1 1 d . . . N1 N 1.0730(2) 0.08697(12) 0.7570(2) 0.0263(5) Uani 1 1 d . . . N2 N 0.9921(3) 0.15597(11) 0.3607(2) 0.0278(6) Uani 1 1 d . . . N3 N 0.4112(2) 0.04401(13) 0.1843(2) 0.0338(6) Uani 1 1 d . . . N4 N 0.5360(3) 0.11839(16) 0.6964(3) 0.0547(8) Uani 1 1 d . . . N5 N 0.8690(3) 0.14867(18) 1.0080(3) 0.0630(9) Uani 1 1 d . . . O1 O 0.3168(2) 0.06687(12) 0.2148(2) 0.0479(6) Uani 1 1 d . . . O2 O 0.4000(2) 0.01673(13) 0.0823(2) 0.0517(6) Uani 1 1 d . . . O3 O 0.72965(19) 0.20807(10) 1.22953(18) 0.0351(5) Uani 1 1 d . . . O4 O 0.28355(18) 0.17350(9) 0.80962(17) 0.0300(5) Uani 1 1 d . . . Cl1 Cl 0.47159(8) 0.24573(4) 1.27419(7) 0.0392(2) Uani 1 1 d . . . Cl2 Cl 0.21988(7) 0.21811(5) 1.04038(7) 0.0430(2) Uani 1 1 d . . . H3A H 0.739(5) 0.255(2) 1.259(5) 0.109(17) Uiso 1 1 d . . . H2 H 0.907(3) 0.1623(16) 0.311(3) 0.044(10) Uiso 1 1 d . . . H1 H 1.133(3) 0.1186(15) 0.760(3) 0.032(8) Uiso 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 0.0241(15) 0.0164(14) 0.0238(14) -0.0044(10) 0.0021(12) 0.0023(11) C2 0.0219(15) 0.0219(14) 0.0258(15) -0.0058(11) 0.0032(12) -0.0007(11) C3 0.0258(15) 0.0304(16) 0.0263(15) -0.0037(12) 0.0056(12) -0.0059(12) C4 0.0387(18) 0.0444(19) 0.0240(15) 0.0000(13) 0.0094(14) -0.0114(15) C5 0.0331(17) 0.0446(19) 0.0209(15) -0.0042(13) 0.0019(13) -0.0062(14) C6 0.0261(16) 0.0201(14) 0.0223(14) -0.0027(11) 0.0031(12) -0.0003(11) C7 0.0214(15) 0.0238(15) 0.0297(15) -0.0043(11) 0.0018(12) 0.0012(11) C8 0.0293(17) 0.0286(16) 0.0482(19) -0.0080(13) 0.0171(15) -0.0054(13) C9 0.048(2) 0.0261(16) 0.0343(17) 0.0017(13) 0.0172(15) -0.0017(14) C10 0.0235(15) 0.0171(14) 0.0256(14) 0.0020(11) 0.0016(12) 0.0014(11) C11 0.0222(15) 0.0214(14) 0.0277(15) -0.0006(11) 0.0038(12) 0.0029(11) C12 0.0314(17) 0.0236(15) 0.0242(14) 0.0000(11) 0.0019(13) -0.0019(12) C13 0.0213(15) 0.0258(15) 0.0298(15) 0.0047(12) -0.0015(12) -0.0034(12) C14 0.0228(16) 0.0322(17) 0.0378(17) 0.0011(13) 0.0069(13) 0.0006(12) C15 0.0288(17) 0.0332(17) 0.0251(15) 0.0000(12) 0.0042(13) 0.0019(13) C16 0.0344(17) 0.0205(15) 0.0244(15) 0.0018(11) 0.0008(13) -0.0004(12) C17 0.0301(17) 0.0174(14) 0.0290(16) 0.0026(11) -0.0050(13) 0.0012(12) C18 0.0263(16) 0.0208(15) 0.0299(16) 0.0046(11) -0.0001(13) 0.0036(11) C19 0.0279(16) 0.0212(15) 0.0245(14) 0.0016(11) 0.0006(12) -0.0020(12) C20 0.0280(16) 0.0193(14) 0.0236(15) 0.0037(11) -0.0015(12) -0.0047(11) C21 0.0272(16) 0.0231(15) 0.0245(15) 0.0035(11) -0.0011(12) -0.0005(11) C22 0.0297(19) 0.0377(18) 0.0312(17) 0.0006(13) -0.0047(14) 0.0003(14) C23 0.0265(17) 0.0298(17) 0.0325(17) 0.0003(13) -0.0012(13) -0.0032(12) N1 0.0251(13) 0.0260(13) 0.0238(13) -0.0047(10) 0.0017(10) -0.0056(11) N2 0.0311(15) 0.0219(13) 0.0271(13) 0.0025(10) 0.0041(12) 0.0023(11) N3 0.0237(14) 0.0364(15) 0.0342(15) 0.0083(11) -0.0017(12) -0.0040(11) N4 0.0484(19) 0.068(2) 0.0464(19) -0.0068(16) 0.0134(15) -0.0014(15) N5 0.046(2) 0.076(2) 0.061(2) -0.0087(17) 0.0076(17) 0.0101(17) O1 0.0232(12) 0.0610(16) 0.0536(15) -0.0001(12) 0.0030(11) -0.0044(11) O2 0.0372(13) 0.0717(17) 0.0337(13) -0.0087(11) -0.0074(11) -0.0062(12) O3 0.0300(12) 0.0271(12) 0.0331(12) -0.0047(9) -0.0122(9) 0.0057(9) O4 0.0272(11) 0.0293(11) 0.0246(10) 0.0002(8) -0.0049(9) -0.0049(8) Cl1 0.0408(5) 0.0406(5) 0.0292(4) -0.0051(3) 0.0008(3) 0.0007(3) Cl2 0.0299(4) 0.0605(6) 0.0337(4) -0.0019(4) 0.0023(3) 0.0035(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 1.407(4) . ? C1 C6 1.416(4) . ? C1 C10 1.486(4) . ? C2 N1 1.398(3) . ? C2 C3 1.418(4) . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 N1 1.340(4) . ? C5 H5 0.9500 . ? C6 N2 1.400(3) . ? C6 C7 1.408(4) . ? C7 C8 1.381(4) . ? C7 H7 0.9500 . ? C8 C9 1.392(4) . ? C8 H8 0.9500 . ? C9 N2 1.335(4) . ? C9 H9 0.9500 . ? C10 C15 1.398(4) . ? C10 C11 1.405(4) . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 N3 1.481(4) . ? C14 C15 1.381(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.391(4) . ? C16 C17 1.407(4) . ? C16 Cl1 1.731(3) . ? C17 O3 1.346(3) . ? C17 C18 1.399(4) . ? C18 C19 1.416(4) . ? C18 C22 1.463(5) . ? C19 C20 1.409(4) . ? C19 C23 1.458(4) . ? C20 O4 1.319(3) . ? C20 C21 1.413(4) . ? C21 Cl2 1.725(3) . ? C22 N5 1.103(4) . ? C23 N4 1.102(4) . ? N1 H1 0.88(3) . ? N2 H2 0.90(3) . ? N3 O2 1.219(3) . ? N3 O1 1.227(3) . ? O3 H3A 0.97(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 C6 124.2(2) . . ? C2 C1 C10 116.8(2) . . ? C6 C1 C10 119.0(2) . . ? N1 C2 C1 126.0(2) . . ? N1 C2 C3 105.9(2) . . ? C1 C2 C3 128.0(2) . . ? C4 C3 C2 108.3(2) . . ? C4 C3 H3 125.8 . . ? C2 C3 H3 125.8 . . ? C3 C4 C5 106.7(3) . . ? C3 C4 H4 126.6 . . ? C5 C4 H4 126.6 . . ? N1 C5 C4 110.0(2) . . ? N1 C5 H5 125.0 . . ? C4 C5 H5 125.0 . . ? N2 C6 C7 105.9(2) . . ? N2 C6 C1 122.2(2) . . ? C7 C6 C1 131.8(2) . . ? C8 C7 C6 108.1(2) . . ? C8 C7 H7 125.9 . . ? C6 C7 H7 125.9 . . ? C7 C8 C9 107.4(3) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N2 C9 C8 109.0(3) . . ? N2 C9 H9 125.5 . . ? C8 C9 H9 125.5 . . ? C15 C10 C11 119.1(2) . . ? C15 C10 C1 120.5(2) . . ? C11 C10 C1 120.4(2) . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 117.8(3) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? C14 C13 C12 122.9(3) . . ? C14 C13 N3 119.0(3) . . ? C12 C13 N3 118.0(2) . . ? C15 C14 C13 118.6(3) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C10 120.6(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C21 C16 C17 121.1(3) . . ? C21 C16 Cl1 119.9(2) . . ? C17 C16 Cl1 119.1(2) . . ? O3 C17 C18 119.5(3) . . ? O3 C17 C16 122.5(3) . . ? C18 C17 C16 118.0(2) . . ? C17 C18 C19 120.8(3) . . ? C17 C18 C22 118.3(2) . . ? C19 C18 C22 120.9(3) . . ? C20 C19 C18 121.3(3) . . ? C20 C19 C23 117.5(2) . . ? C18 C19 C23 121.1(2) . . ? O4 C20 C19 120.9(2) . . ? O4 C20 C21 122.3(2) . . ? C19 C20 C21 116.8(2) . . ? C16 C21 C20 121.9(3) . . ? C16 C21 Cl2 120.1(2) . . ? C20 C21 Cl2 118.0(2) . . ? N5 C22 C18 176.8(4) . . ? N4 C23 C19 178.2(3) . . ? C5 N1 C2 109.0(2) . . ? C5 N1 H1 122.4(19) . . ? C2 N1 H1 128.6(19) . . ? C9 N2 C6 109.6(3) . . ? C9 N2 H2 125(2) . . ? C6 N2 H2 125(2) . . ? O2 N3 O1 123.9(2) . . ? O2 N3 C13 118.6(2) . . ? O1 N3 C13 117.4(2) . . ? C17 O3 H3A 112(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 C6 C1 C2 N1 16.9(4) . . . . ? C10 C1 C2 N1 -165.4(2) . . . . ? C6 C1 C2 C3 -158.6(3) . . . . ? C10 C1 C2 C3 19.1(4) . . . . ? N1 C2 C3 C4 -0.8(3) . . . . ? C1 C2 C3 C4 175.4(3) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 N1 -1.2(4) . . . . ? C2 C1 C6 N2 -167.8(2) . . . . ? C10 C1 C6 N2 14.5(4) . . . . ? C2 C1 C6 C7 16.6(4) . . . . ? C10 C1 C6 C7 -161.0(3) . . . . ? N2 C6 C7 C8 -0.3(3) . . . . ? C1 C6 C7 C8 175.8(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 N2 -0.3(3) . . . . ? C2 C1 C10 C15 47.1(3) . . . . ? C6 C1 C10 C15 -135.1(3) . . . . ? C2 C1 C10 C11 -133.4(3) . . . . ? C6 C1 C10 C11 44.4(3) . . . . ? C15 C10 C11 C12 0.5(4) . . . . ? C1 C10 C11 C12 -179.0(2) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 C14 -1.7(4) . . . . ? C11 C12 C13 N3 175.8(2) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? N3 C13 C14 C15 -176.4(2) . . . . ? C13 C14 C15 C10 0.3(4) . . . . ? C11 C10 C15 C14 -1.1(4) . . . . ? C1 C10 C15 C14 178.4(2) . . . . ? C21 C16 C17 O3 -179.5(2) . . . . ? Cl1 C16 C17 O3 1.4(4) . . . . ? C21 C16 C17 C18 -1.3(4) . . . . ? Cl1 C16 C17 C18 179.6(2) . . . . ? O3 C17 C18 C19 -179.5(2) . . . . ? C16 C17 C18 C19 2.3(4) . . . . ? O3 C17 C18 C22 -2.4(4) . . . . ? C16 C17 C18 C22 179.4(2) . . . . ? C17 C18 C19 C20 -0.1(4) . . . . ? C22 C18 C19 C20 -177.0(3) . . . . ? C17 C18 C19 C23 176.4(3) . . . . ? C22 C18 C19 C23 -0.6(4) . . . . ? C18 C19 C20 O4 174.0(2) . . . . ? C23 C19 C20 O4 -2.5(4) . . . . ? C18 C19 C20 C21 -3.1(4) . . . . ? C23 C19 C20 C21 -179.7(2) . . . . ? C17 C16 C21 C20 -2.0(4) . . . . ? Cl1 C16 C21 C20 177.1(2) . . . . ? C17 C16 C21 Cl2 178.8(2) . . . . ? Cl1 C16 C21 Cl2 -2.1(3) . . . . ? O4 C20 C21 C16 -173.0(2) . . . . ? C19 C20 C21 C16 4.2(4) . . . . ? O4 C20 C21 Cl2 6.2(4) . . . . ? C19 C20 C21 Cl2 -176.67(19) . . . . ? C17 C18 C22 N5 -35(7) . . . . ? C19 C18 C22 N5 142(6) . . . . ? C20 C19 C23 N4 7(11) . . . . ? C18 C19 C23 N4 -169(100) . . . . ? C4 C5 N1 C2 0.7(3) . . . . ? C1 C2 N1 C5 -176.2(3) . . . . ? C3 C2 N1 C5 0.1(3) . . . . ? C8 C9 N2 C6 0.2(3) . . . . ? C7 C6 N2 C9 0.1(3) . . . . ? C1 C6 N2 C9 -176.5(2) . . . . ? C14 C13 N3 O2 -174.6(3) . . . . ? C12 C13 N3 O2 7.8(4) . . . . ? C14 C13 N3 O1 7.5(4) . . . . ? C12 C13 N3 O1 -170.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.315 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.081