# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jubaraj Baruah' _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Formation of Symmetry Non Equivalent Molecules in Urea and Carbamate Derivatives: Role of Anion ; loop_ _publ_author_name 'Jubaraj Baruah' 'Dipjyoti Kalita' 'Rupam Sarma' # Attachment '1a.cif' data_5aqphnco _database_code_depnum_ccdc_archive 'CCDC 695409' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N3 O' _chemical_formula_weight 263.29 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 Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 12.3447(3) _cell_length_b 4.59570(10) _cell_length_c 11.4845(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.416(2) _cell_angle_gamma 90.00 _cell_volume 648.64(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5296 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1935 _reflns_number_gt 1857 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0301P)^2^+0.0828P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(3) _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 -0.5(13) _refine_ls_number_reflns 1935 _refine_ls_number_parameters 176 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.37448(17) 0.3893(4) 0.84750(19) 0.062 Uani 1 1 d . . . H1 H 0.3668 0.4663 0.9212 0.075 Uiso 1 1 calc R . . C2 C 0.46000(18) 0.4760(5) 0.7853(3) 0.0806(7) Uani 1 1 d . . . H2 H 0.5085 0.6162 0.8169 0.097 Uiso 1 1 calc R . . C3 C 0.47412(18) 0.3595(5) 0.6788(2) 0.0750(7) Uani 1 1 d . . . H3 H 0.5327 0.4158 0.6388 0.090 Uiso 1 1 calc R . . C4 C 0.40217(19) 0.1616(5) 0.6321(2) 0.0743(6) Uani 1 1 d . . . H4 H 0.4115 0.0809 0.5594 0.089 Uiso 1 1 calc R . . C5 C 0.31484(16) 0.0771(5) 0.69044(17) 0.0614(5) Uani 1 1 d . . . H5 H 0.2648 -0.0561 0.6562 0.074 Uiso 1 1 calc R . . C6 C 0.30146(13) 0.1889(3) 0.79898(15) 0.0420(4) Uani 1 1 d . . . C7 C 0.14718(14) 0.2506(3) 0.91799(16) 0.0384(3) Uani 1 1 d . . . C8 C -0.00537(14) 0.2363(3) 1.03877(14) 0.0394(4) Uani 1 1 d . . . C9 C 0.02550(15) 0.4307(4) 1.12586(15) 0.0481(4) Uani 1 1 d . . . H9 H 0.0988 0.4730 1.1441 0.058 Uiso 1 1 calc R . . C10 C -0.05345(18) 0.5664(4) 1.18779(16) 0.0549(5) Uani 1 1 d . . . H10 H -0.0318 0.7016 1.2456 0.066 Uiso 1 1 calc R . . C11 C -0.16040(17) 0.5040(4) 1.16481(15) 0.0533(5) Uani 1 1 d . . . H11 H -0.2112 0.5945 1.2074 0.064 Uiso 1 1 calc R . . C12 C -0.19520(14) 0.3025(3) 1.07667(15) 0.0457(4) Uani 1 1 d . . . C13 C -0.33529(18) 0.0682(5) 0.9711(2) 0.0719(6) Uani 1 1 d . . . H13 H -0.4093 0.0299 0.9568 0.086 Uiso 1 1 calc R . . C14 C -0.26486(16) -0.0694(5) 0.89996(18) 0.0633(5) Uani 1 1 d . . . H14 H -0.2921 -0.1921 0.8398 0.076 Uiso 1 1 calc R . . C15 C -0.15682(15) -0.0215(4) 0.92001(15) 0.0488(4) Uani 1 1 d . . . H15 H -0.1087 -0.1132 0.8743 0.059 Uiso 1 1 calc R . . C16 C -0.11723(13) 0.1693(3) 1.01103(14) 0.0394(4) Uani 1 1 d . . . N1 N 0.21435(12) 0.0837(3) 0.86044(13) 0.0478(4) Uani 1 1 d . . . H1A H 0.2038 -0.1012 0.8608 0.057 Uiso 1 1 calc R . . N2 N 0.07290(12) 0.0994(2) 0.97420(12) 0.0430(3) Uani 1 1 d . . . H2A H 0.0734 -0.0875 0.9704 0.052 Uiso 1 1 calc R . . N3 N -0.30420(13) 0.2470(4) 1.05652(16) 0.0637(5) Uani 1 1 d . . . O1 O 0.15030(11) 0.51808(19) 0.91802(13) 0.0533(3) 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 0.056 0.059 0.072 -0.013 0.011 -0.015 C2 0.0503(13) 0.0721(13) 0.120(2) -0.0102(13) 0.0144(13) -0.0247(10) C3 0.0569(13) 0.0744(14) 0.0988(18) 0.0189(13) 0.0337(13) -0.0054(11) C4 0.0742(15) 0.0889(16) 0.0641(14) 0.0013(11) 0.0286(12) -0.0070(13) C5 0.0582(12) 0.0691(12) 0.0586(13) -0.0086(9) 0.0153(10) -0.0156(9) C6 0.0405(9) 0.0320(7) 0.0547(11) 0.0053(7) 0.0107(8) -0.0004(6) C7 0.0407(8) 0.0269(6) 0.0482(8) 0.0019(7) 0.0069(6) -0.0010(7) C8 0.0456(10) 0.0296(7) 0.0448(10) 0.0064(7) 0.0129(8) 0.0035(7) C9 0.0500(10) 0.0436(8) 0.0506(11) -0.0014(7) 0.0036(8) 0.0018(8) C10 0.0725(13) 0.0482(9) 0.0443(10) -0.0074(8) 0.0079(9) 0.0067(9) C11 0.0647(14) 0.0504(9) 0.0480(11) 0.0006(8) 0.0219(10) 0.0115(9) C12 0.0467(10) 0.0408(8) 0.0520(11) 0.0089(7) 0.0167(8) 0.0053(8) C13 0.0474(12) 0.0776(13) 0.0921(17) -0.0046(12) 0.0143(12) -0.0104(10) C14 0.0535(13) 0.0684(12) 0.0693(14) -0.0097(10) 0.0128(11) -0.0171(10) C15 0.0524(12) 0.0423(8) 0.0544(11) -0.0022(7) 0.0184(9) -0.0054(7) C16 0.0477(9) 0.0307(7) 0.0416(9) 0.0071(6) 0.0123(8) 0.0010(7) N1 0.0504(9) 0.0247(6) 0.0722(10) -0.0015(6) 0.0265(7) -0.0045(6) N2 0.0447(8) 0.0243(6) 0.0625(9) 0.0010(6) 0.0182(7) 0.0007(6) N3 0.0486(10) 0.0665(10) 0.0791(13) 0.0001(9) 0.0213(9) 0.0032(8) O1 0.0607(7) 0.0247(5) 0.0780(8) 0.0002(6) 0.0257(6) -0.0019(6) _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 1.370(3) . ? C1 C2 1.388(3) . ? C2 C3 1.361(4) . ? C3 C4 1.347(3) . ? C4 C5 1.378(3) . ? C5 C6 1.373(3) . ? C6 N1 1.425(2) . ? C7 O1 1.2301(15) . ? C7 N1 1.3474(19) . ? C7 N2 1.361(2) . ? C8 C9 1.368(2) . ? C8 N2 1.419(2) . ? C8 C16 1.421(2) . ? C9 C10 1.406(3) . ? C10 C11 1.353(3) . ? C11 C12 1.409(3) . ? C12 N3 1.368(2) . ? C12 C16 1.416(2) . ? C13 N3 1.309(3) . ? C13 C14 1.399(3) . ? C14 C15 1.350(3) . ? C15 C16 1.416(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 C6 C1 C2 119.1(2) . . ? C3 C2 C1 121.2(2) . . ? C4 C3 C2 119.22(19) . . ? C3 C4 C5 120.9(2) . . ? C6 C5 C4 120.21(18) . . ? C1 C6 C5 119.35(17) . . ? C1 C6 N1 121.65(16) . . ? C5 C6 N1 118.94(15) . . ? O1 C7 N1 123.25(15) . . ? O1 C7 N2 122.18(15) . . ? N1 C7 N2 114.55(10) . . ? C9 C8 N2 121.00(16) . . ? C9 C8 C16 120.20(16) . . ? N2 C8 C16 118.80(14) . . ? C8 C9 C10 120.08(18) . . ? C11 C10 C9 121.18(17) . . ? C10 C11 C12 120.37(17) . . ? N3 C12 C11 118.20(17) . . ? N3 C12 C16 122.44(15) . . ? C11 C12 C16 119.34(16) . . ? N3 C13 C14 124.54(19) . . ? C15 C14 C13 119.01(19) . . ? C14 C15 C16 119.58(18) . . ? C12 C16 C15 117.14(15) . . ? C12 C16 C8 118.80(14) . . ? C15 C16 C8 124.06(15) . . ? C7 N1 C6 125.31(12) . . ? C7 N2 C8 122.95(11) . . ? C13 N3 C12 117.26(18) . . ? 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 C3 -1.9(4) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C2 C1 C6 N1 177.68(19) . . . . ? C4 C5 C6 C1 1.3(3) . . . . ? C4 C5 C6 N1 -176.05(19) . . . . ? N2 C8 C9 C10 179.25(15) . . . . ? C16 C8 C9 C10 -0.4(2) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 N3 -179.87(17) . . . . ? C10 C11 C12 C16 -1.0(2) . . . . ? N3 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? N3 C12 C16 C15 1.6(2) . . . . ? C11 C12 C16 C15 -177.22(16) . . . . ? N3 C12 C16 C8 -179.17(17) . . . . ? C11 C12 C16 C8 2.0(2) . . . . ? C14 C15 C16 C12 -0.3(2) . . . . ? C14 C15 C16 C8 -179.50(17) . . . . ? C9 C8 C16 C12 -1.3(2) . . . . ? N2 C8 C16 C12 179.03(13) . . . . ? C9 C8 C16 C15 177.86(15) . . . . ? N2 C8 C16 C15 -1.8(2) . . . . ? O1 C7 N1 C6 4.3(3) . . . . ? N2 C7 N1 C6 -177.39(14) . . . . ? C1 C6 N1 C7 47.0(3) . . . . ? C5 C6 N1 C7 -135.70(19) . . . . ? O1 C7 N2 C8 -1.1(3) . . . . ? N1 C7 N2 C8 -179.48(15) . . . . ? C9 C8 N2 C7 -54.2(2) . . . . ? C16 C8 N2 C7 125.42(16) . . . . ? C14 C13 N3 C12 0.2(3) . . . . ? C11 C12 N3 C13 177.30(18) . . . . ? C16 C12 N3 C13 -1.5(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 N2 H2A O1 0.86 2.16 2.9295(15) 149.1 1_545 N1 H1A O1 0.86 2.00 2.8140(15) 156.9 1_545 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.107 _refine_diff_density_min -0.107 _refine_diff_density_rms 0.023 # Attachment '2b.cif' data_8aqphen _database_code_depnum_ccdc_archive 'CCDC 695411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl N3 O5' _chemical_formula_weight 363.75 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.584(5) _cell_length_b 8.0620(19) _cell_length_c 20.523(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3240.3(14) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22668 _diffrn_reflns_av_R_equivalents 0.1122 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.27 _reflns_number_total 7708 _reflns_number_gt 3202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.39(10) _refine_ls_number_reflns 7708 _refine_ls_number_parameters 451 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1926 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.1806 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.240 _refine_ls_restrained_S_all 1.240 _refine_ls_shift/su_max 0.001 _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 -0.1177(3) 0.3250(10) 0.3461(3) 0.0642(18) Uani 1 1 d . . . H1 H -0.1325 0.2515 0.3780 0.077 Uiso 1 1 calc R . . C2 C -0.1644(3) 0.3878(10) 0.3028(4) 0.073(2) Uani 1 1 d . . . H2 H -0.2108 0.3648 0.3071 0.088 Uiso 1 1 calc R . . C3 C -0.1403(3) 0.4876(10) 0.2520(4) 0.068(2) Uani 1 1 d . . . H3 H -0.1708 0.5285 0.2213 0.081 Uiso 1 1 calc R . . C4 C -0.0716(3) 0.5266(8) 0.2468(3) 0.0542(16) Uani 1 1 d . . . C5 C -0.0438(4) 0.6202(9) 0.1968(3) 0.0619(18) Uani 1 1 d . . . H5 H -0.0722 0.6594 0.1639 0.074 Uiso 1 1 calc R . . C6 C 0.0251(4) 0.6568(9) 0.1947(3) 0.0715(19) Uani 1 1 d . . . H6 H 0.0429 0.7211 0.1611 0.086 Uiso 1 1 calc R . . C7 C 0.0685(3) 0.5945(9) 0.2447(3) 0.0644(18) Uani 1 1 d . . . H7 H 0.1148 0.6197 0.2434 0.077 Uiso 1 1 calc R . . C8 C 0.0447(3) 0.5012(8) 0.2932(3) 0.0486(16) Uani 1 1 d . . . C9 C -0.0262(3) 0.4653(7) 0.2958(3) 0.0494(15) Uani 1 1 d . . . C10 C 0.0989(3) 0.5172(9) 0.4003(3) 0.0463(15) Uani 1 1 d . . . C11 C 0.1755(3) 0.5212(8) 0.4958(3) 0.0503(16) Uani 1 1 d . . . C12 C 0.1352(3) 0.6066(9) 0.5405(3) 0.0598(18) Uani 1 1 d . . . H12 H 0.0889 0.6217 0.5324 0.072 Uiso 1 1 calc R . . C13 C 0.1639(3) 0.6687(11) 0.5966(3) 0.074(2) Uani 1 1 d . . . H13 H 0.1365 0.7230 0.6268 0.088 Uiso 1 1 calc R . . C15 C 0.2706(3) 0.5658(10) 0.5658(4) 0.075(2) Uani 1 1 d . . . H15 H 0.3166 0.5482 0.5746 0.089 Uiso 1 1 calc R . . C16 C 0.2434(3) 0.5005(9) 0.5075(3) 0.066(2) Uani 1 1 d . . . H16 H 0.2711 0.4448 0.4779 0.079 Uiso 1 1 calc R . . C17 C 0.3642(4) -0.1985(10) 0.4292(5) 0.086(2) Uani 1 1 d . . . H17 H 0.3795 -0.2679 0.3961 0.104 Uiso 1 1 calc R . . C18 C 0.4093(4) -0.1365(12) 0.4786(5) 0.094(3) Uani 1 1 d . . . H18 H 0.4555 -0.1625 0.4758 0.112 Uiso 1 1 calc R . . C19 C 0.3883(4) -0.0445(11) 0.5275(4) 0.078(2) Uani 1 1 d . . . H19 H 0.4190 -0.0094 0.5593 0.094 Uiso 1 1 calc R . . C20 C 0.3168(3) 0.0015(9) 0.5314(3) 0.0554(17) Uani 1 1 d . . . C21 C 0.2916(4) 0.0978(11) 0.5832(4) 0.081(2) Uani 1 1 d . . . H21 H 0.3204 0.1349 0.6162 0.097 Uiso 1 1 calc R . . C22 C 0.2241(4) 0.1349(11) 0.5838(4) 0.088(2) Uani 1 1 d . . . H22 H 0.2063 0.1989 0.6175 0.106 Uiso 1 1 calc R . . C23 C 0.1813(3) 0.0783(10) 0.5347(3) 0.0676(19) Uani 1 1 d . . . H23 H 0.1352 0.1055 0.5363 0.081 Uiso 1 1 calc R . . C24 C 0.2045(3) -0.0151(9) 0.4845(4) 0.0610(19) Uani 1 1 d . . . C25 C 0.2733(3) -0.0567(8) 0.4835(3) 0.0512(16) Uani 1 1 d . . . C26 C 0.1476(3) 0.0166(9) 0.3807(3) 0.0533(16) Uani 1 1 d . . . C27 C 0.0706(3) 0.0293(8) 0.2844(3) 0.0519(17) Uani 1 1 d . . . C28 C -0.0007(3) 0.0141(9) 0.2724(3) 0.0633(19) Uani 1 1 d . . . H28 H -0.0288 -0.0390 0.3023 0.076 Uiso 1 1 calc R . . C29 C -0.0276(4) 0.0796(10) 0.2155(3) 0.067(2) Uani 1 1 d . . . H29 H -0.0742 0.0724 0.2071 0.080 Uiso 1 1 calc R . . C30 C 0.0147(4) 0.1545(10) 0.1720(4) 0.077(2) Uani 1 1 d . . . H30 H -0.0034 0.1960 0.1334 0.092 Uiso 1 1 calc R . . C31 C 0.0831(4) 0.1704(11) 0.1835(3) 0.077(2) Uani 1 1 d . . . H31 H 0.1103 0.2267 0.1537 0.092 Uiso 1 1 calc R . . C32 C 0.1120(3) 0.1037(10) 0.2387(3) 0.069(2) Uani 1 1 d . . . H32 H 0.1590 0.1090 0.2452 0.082 Uiso 1 1 calc R . . C33 C 0.2341(3) 0.6511(10) 0.6087(3) 0.075(2) Uani 1 1 d . . . H33 H 0.2542 0.6975 0.6455 0.090 Uiso 1 1 calc R . . Cl2 Cl 0.27121(9) 0.5857(3) 0.28752(9) 0.0788(6) Uani 1 1 d . . . Cl3 Cl 0.97677(9) 0.1091(3) 0.49322(8) 0.0726(5) Uani 1 1 d . . . N1 N 0.0875(2) 0.4325(7) 0.3433(2) 0.0566(14) Uani 1 1 d . . . H1A H 0.1063 0.3371 0.3375 0.068 Uiso 1 1 calc R . . N2 N 0.1486(2) 0.4499(7) 0.4374(2) 0.0564(14) Uani 1 1 d . . . H2A H 0.1654 0.3566 0.4250 0.068 Uiso 1 1 calc R . . N3 N -0.0529(2) 0.3653(7) 0.3438(2) 0.0582(14) Uani 1 1 d . . . H3A H -0.0260 0.3278 0.3735 0.070 Uiso 1 1 calc R . . N4 N 0.2989(2) -0.1509(7) 0.4335(3) 0.0614(14) Uani 1 1 d . . . H4A H 0.2713 -0.1812 0.4032 0.074 Uiso 1 1 calc R . . N5 N 0.1601(2) -0.0736(7) 0.4338(2) 0.0560(13) Uani 1 1 d . . . H5A H 0.1411 -0.1693 0.4378 0.067 Uiso 1 1 calc R . . N6 N 0.0954(2) -0.0438(7) 0.3422(2) 0.0541(14) Uani 1 1 d . . . H6A H 0.0763 -0.1344 0.3547 0.065 Uiso 1 1 calc R . . O1 O 0.06602(19) 0.6424(6) 0.41449(18) 0.0590(12) Uani 1 1 d . . . O2 O 0.1815(2) 0.1417(6) 0.36567(18) 0.0605(12) Uani 1 1 d . . . O8 O 0.2337(3) 0.4586(9) 0.2570(4) 0.134(2) Uani 1 1 d . . . O14 O 1.0135(3) 0.2150(10) 0.4515(3) 0.143(3) Uani 1 1 d . . . O15 O 1.0136(3) -0.0326(9) 0.5087(4) 0.148(3) Uani 1 1 d . . . O17 O 0.9752(8) 0.1955(16) 0.5473(3) 0.314(9) Uani 1 1 d . . . O18 O 0.2356(3) 0.7123(11) 0.3112(6) 0.216(5) Uani 1 1 d . . . O19 O 0.9151(4) 0.0990(15) 0.4726(9) 0.329(10) Uani 1 1 d . . . O20 O 0.2929(6) 0.5026(14) 0.3452(4) 0.237(5) Uani 1 1 d . . . O21 O 0.3327(3) 0.6198(10) 0.2631(5) 0.200(4) 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 0.054(4) 0.087(6) 0.052(4) 0.007(4) 0.004(3) -0.012(4) C2 0.043(4) 0.109(7) 0.069(5) -0.033(5) -0.009(3) 0.012(4) C3 0.046(4) 0.090(6) 0.067(5) -0.011(4) -0.012(3) 0.002(4) C4 0.057(4) 0.055(5) 0.051(4) -0.006(3) -0.013(3) 0.019(3) C5 0.081(5) 0.061(5) 0.043(4) -0.001(3) -0.017(3) 0.005(4) C6 0.079(5) 0.076(6) 0.060(4) 0.009(4) 0.009(4) 0.000(4) C7 0.049(4) 0.078(6) 0.066(4) 0.010(4) 0.003(3) 0.002(3) C8 0.040(3) 0.057(4) 0.049(4) -0.005(3) -0.012(3) 0.005(3) C9 0.057(4) 0.042(4) 0.049(4) -0.014(3) 0.003(3) 0.008(3) C10 0.027(3) 0.068(5) 0.044(4) 0.014(4) 0.001(2) -0.009(3) C11 0.047(4) 0.062(4) 0.042(4) 0.004(3) 0.003(3) 0.002(3) C12 0.051(3) 0.095(6) 0.033(3) 0.008(3) 0.004(3) 0.005(4) C13 0.070(5) 0.099(7) 0.052(4) 0.006(4) 0.001(4) 0.015(4) C15 0.056(4) 0.091(7) 0.076(5) 0.014(5) -0.008(4) -0.011(4) C16 0.046(4) 0.092(6) 0.059(5) -0.012(4) -0.006(3) -0.005(4) C17 0.049(4) 0.074(6) 0.136(7) 0.016(5) 0.019(5) 0.007(4) C18 0.043(4) 0.111(8) 0.127(8) 0.018(6) 0.007(5) -0.008(4) C19 0.073(5) 0.086(6) 0.076(5) 0.017(5) -0.018(4) -0.017(4) C20 0.048(4) 0.060(5) 0.058(4) 0.011(4) -0.015(3) -0.007(3) C21 0.084(6) 0.087(7) 0.071(5) 0.001(5) -0.018(4) -0.008(4) C22 0.079(5) 0.101(7) 0.085(5) -0.028(5) -0.014(4) 0.013(5) C23 0.065(4) 0.077(6) 0.061(4) -0.001(4) -0.007(4) 0.007(4) C24 0.050(4) 0.066(5) 0.067(5) 0.011(4) 0.009(4) -0.001(3) C25 0.045(4) 0.053(4) 0.056(4) 0.001(3) -0.006(3) -0.001(3) C26 0.045(4) 0.049(4) 0.066(4) 0.000(4) 0.009(3) 0.003(4) C27 0.055(4) 0.057(4) 0.044(4) -0.009(4) -0.012(3) 0.018(3) C28 0.053(4) 0.062(5) 0.075(5) -0.006(4) -0.006(3) 0.000(3) C29 0.060(4) 0.092(6) 0.048(4) 0.006(4) -0.015(4) 0.008(4) C30 0.076(5) 0.088(6) 0.066(5) -0.020(4) -0.030(4) 0.027(5) C31 0.080(5) 0.105(7) 0.045(4) 0.017(4) 0.020(4) 0.019(5) C32 0.053(4) 0.098(6) 0.055(4) 0.003(4) 0.018(3) 0.005(4) C33 0.064(5) 0.102(6) 0.060(5) -0.010(4) 0.003(4) -0.009(4) Cl2 0.0533(10) 0.0932(15) 0.0898(14) -0.0146(13) 0.0117(10) -0.0087(10) Cl3 0.0619(10) 0.0891(14) 0.0669(11) 0.0066(11) 0.0127(9) 0.0029(10) N1 0.054(3) 0.059(4) 0.057(3) -0.006(3) -0.012(3) 0.008(3) N2 0.047(3) 0.058(4) 0.065(4) -0.007(3) -0.006(3) 0.010(2) N3 0.043(3) 0.077(4) 0.055(3) 0.003(3) 0.009(2) 0.003(3) N4 0.050(3) 0.067(4) 0.067(4) 0.015(3) -0.001(3) 0.005(3) N5 0.056(3) 0.056(4) 0.056(3) 0.007(3) -0.019(3) 0.004(2) N6 0.047(3) 0.061(4) 0.054(3) 0.003(3) -0.008(2) -0.002(2) O1 0.046(2) 0.064(3) 0.067(3) -0.005(2) 0.007(2) 0.015(2) O2 0.054(2) 0.075(4) 0.053(3) 0.002(2) -0.0127(19) 0.001(2) O8 0.103(4) 0.132(6) 0.167(6) -0.064(5) -0.027(4) -0.004(4) O14 0.103(4) 0.216(8) 0.112(4) 0.091(5) 0.005(3) -0.017(4) O15 0.091(4) 0.109(5) 0.243(8) 0.057(5) 0.014(5) 0.032(4) O17 0.59(2) 0.305(15) 0.050(4) -0.053(6) -0.027(7) 0.256(15) O18 0.071(4) 0.149(7) 0.428(16) -0.136(9) -0.035(6) 0.041(4) O19 0.098(5) 0.310(15) 0.58(3) 0.294(17) -0.077(9) -0.080(7) O20 0.372(15) 0.213(11) 0.128(6) -0.003(7) -0.109(8) 0.040(9) O21 0.092(4) 0.151(7) 0.357(12) -0.016(7) 0.120(6) -0.024(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 N3 1.310(7) . ? C1 C2 1.373(9) . ? C2 C3 1.399(10) . ? C3 C4 1.384(8) . ? C4 C5 1.385(9) . ? C4 C9 1.430(8) . ? C5 C6 1.382(9) . ? C6 C7 1.424(9) . ? C7 C8 1.333(8) . ? C8 C9 1.419(8) . ? C8 N1 1.438(7) . ? C9 N3 1.378(7) . ? C10 O1 1.232(7) . ? C10 N2 1.349(7) . ? C10 N1 1.373(8) . ? C11 C16 1.362(8) . ? C11 C12 1.391(8) . ? C11 N2 1.430(7) . ? C12 C13 1.375(9) . ? C13 C33 1.403(9) . ? C15 C33 1.326(9) . ? C15 C16 1.411(9) . ? C17 N4 1.338(8) . ? C17 C18 1.434(12) . ? C18 C19 1.314(11) . ? C19 C20 1.451(10) . ? C20 C25 1.383(8) . ? C20 C21 1.406(9) . ? C21 C22 1.355(9) . ? C22 C23 1.388(9) . ? C23 C24 1.355(9) . ? C24 C25 1.389(8) . ? C24 N5 1.434(8) . ? C25 N4 1.371(7) . ? C26 O2 1.246(7) . ? C26 N5 1.334(8) . ? C26 N6 1.379(8) . ? C27 C32 1.377(9) . ? C27 N6 1.412(7) . ? C27 C28 1.422(9) . ? C28 C29 1.386(9) . ? C29 C30 1.358(10) . ? C30 C31 1.365(9) . ? C31 C32 1.378(10) . ? Cl2 O18 1.329(7) . ? Cl2 O21 1.333(5) . ? Cl2 O8 1.408(6) . ? Cl2 O20 1.424(8) . ? Cl3 O19 1.281(8) . ? Cl3 O17 1.311(8) . ? Cl3 O15 1.387(6) . ? Cl3 O14 1.407(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 N3 C1 C2 122.1(7) . . ? C1 C2 C3 118.0(6) . . ? C4 C3 C2 121.1(7) . . ? C3 C4 C5 124.3(6) . . ? C3 C4 C9 118.1(6) . . ? C5 C4 C9 117.6(6) . . ? C6 C5 C4 121.6(6) . . ? C5 C6 C7 119.0(6) . . ? C8 C7 C6 121.9(6) . . ? C7 C8 C9 119.0(6) . . ? C7 C8 N1 123.2(5) . . ? C9 C8 N1 117.8(6) . . ? N3 C9 C8 121.2(6) . . ? N3 C9 C4 118.0(5) . . ? C8 C9 C4 120.8(6) . . ? O1 C10 N2 124.9(6) . . ? O1 C10 N1 121.6(5) . . ? N2 C10 N1 113.5(6) . . ? C16 C11 C12 119.8(6) . . ? C16 C11 N2 117.3(6) . . ? C12 C11 N2 122.8(5) . . ? C13 C12 C11 120.0(6) . . ? C12 C13 C33 120.8(7) . . ? C33 C15 C16 123.5(6) . . ? C11 C16 C15 118.2(6) . . ? N4 C17 C18 116.3(8) . . ? C19 C18 C17 122.9(7) . . ? C18 C19 C20 119.2(7) . . ? C25 C20 C21 120.5(6) . . ? C25 C20 C19 118.0(7) . . ? C21 C20 C19 121.5(7) . . ? C22 C21 C20 118.1(7) . . ? C21 C22 C23 120.6(7) . . ? C24 C23 C22 122.3(7) . . ? C23 C24 C25 117.9(7) . . ? C23 C24 N5 122.1(6) . . ? C25 C24 N5 119.9(6) . . ? N4 C25 C20 119.7(5) . . ? N4 C25 C24 119.9(6) . . ? C20 C25 C24 120.4(6) . . ? O2 C26 N5 123.0(6) . . ? O2 C26 N6 122.6(6) . . ? N5 C26 N6 114.3(6) . . ? C32 C27 N6 123.4(6) . . ? C32 C27 C28 119.9(6) . . ? N6 C27 C28 116.6(6) . . ? C29 C28 C27 119.1(7) . . ? C30 C29 C28 119.4(6) . . ? C29 C30 C31 121.8(7) . . ? C30 C31 C32 120.6(7) . . ? C31 C32 C27 119.2(6) . . ? C15 C33 C13 117.6(7) . . ? O18 Cl2 O21 117.0(6) . . ? O18 Cl2 O8 116.6(4) . . ? O21 Cl2 O8 117.0(5) . . ? O18 Cl2 O20 102.4(7) . . ? O21 Cl2 O20 98.0(7) . . ? O8 Cl2 O20 100.6(6) . . ? O19 Cl3 O17 106.9(10) . . ? O19 Cl3 O15 120.8(6) . . ? O17 Cl3 O15 104.8(6) . . ? O19 Cl3 O14 108.6(5) . . ? O17 Cl3 O14 101.8(8) . . ? O15 Cl3 O14 111.9(4) . . ? C10 N1 C8 120.8(5) . . ? C10 N2 C11 125.3(6) . . ? C1 N3 C9 122.6(5) . . ? C17 N4 C25 123.8(6) . . ? C26 N5 C24 121.6(6) . . ? C26 N6 C27 126.1(6) . . ? 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 N3 C1 C2 C3 5.0(11) . . . . ? C1 C2 C3 C4 -2.1(11) . . . . ? C2 C3 C4 C5 177.9(7) . . . . ? C2 C3 C4 C9 -1.5(10) . . . . ? C3 C4 C5 C6 179.2(7) . . . . ? C9 C4 C5 C6 -1.4(10) . . . . ? C4 C5 C6 C7 0.9(10) . . . . ? C5 C6 C7 C8 0.4(11) . . . . ? C6 C7 C8 C9 -1.1(10) . . . . ? C6 C7 C8 N1 178.1(6) . . . . ? C7 C8 C9 N3 178.0(6) . . . . ? N1 C8 C9 N3 -1.3(8) . . . . ? C7 C8 C9 C4 0.6(9) . . . . ? N1 C8 C9 C4 -178.7(5) . . . . ? C3 C4 C9 N3 2.6(8) . . . . ? C5 C4 C9 N3 -176.8(6) . . . . ? C3 C4 C9 C8 -179.9(6) . . . . ? C5 C4 C9 C8 0.7(9) . . . . ? C16 C11 C12 C13 -0.6(10) . . . . ? N2 C11 C12 C13 178.4(6) . . . . ? C11 C12 C13 C33 1.8(11) . . . . ? C12 C11 C16 C15 0.8(10) . . . . ? N2 C11 C16 C15 -178.2(6) . . . . ? C33 C15 C16 C11 -2.4(11) . . . . ? N4 C17 C18 C19 3.2(13) . . . . ? C17 C18 C19 C20 -1.9(13) . . . . ? C18 C19 C20 C25 1.2(11) . . . . ? C18 C19 C20 C21 179.1(8) . . . . ? C25 C20 C21 C22 -1.7(11) . . . . ? C19 C20 C21 C22 -179.5(7) . . . . ? C20 C21 C22 C23 0.3(12) . . . . ? C21 C22 C23 C24 -0.1(12) . . . . ? C22 C23 C24 C25 1.1(11) . . . . ? C22 C23 C24 N5 179.9(7) . . . . ? C21 C20 C25 N4 -179.8(7) . . . . ? C19 C20 C25 N4 -1.8(9) . . . . ? C21 C20 C25 C24 2.7(10) . . . . ? C19 C20 C25 C24 -179.3(6) . . . . ? C23 C24 C25 N4 -179.9(6) . . . . ? N5 C24 C25 N4 1.3(10) . . . . ? C23 C24 C25 C20 -2.4(10) . . . . ? N5 C24 C25 C20 178.8(6) . . . . ? C32 C27 C28 C29 -2.0(10) . . . . ? N6 C27 C28 C29 -178.3(6) . . . . ? C27 C28 C29 C30 1.0(11) . . . . ? C28 C29 C30 C31 -1.4(12) . . . . ? C29 C30 C31 C32 2.9(12) . . . . ? C30 C31 C32 C27 -3.8(11) . . . . ? N6 C27 C32 C31 179.4(7) . . . . ? C28 C27 C32 C31 3.4(10) . . . . ? C16 C15 C33 C13 3.5(11) . . . . ? C12 C13 C33 C15 -3.2(11) . . . . ? O1 C10 N1 C8 10.2(8) . . . . ? N2 C10 N1 C8 -169.8(5) . . . . ? C7 C8 N1 C10 91.5(7) . . . . ? C9 C8 N1 C10 -89.3(7) . . . . ? O1 C10 N2 C11 -6.4(9) . . . . ? N1 C10 N2 C11 173.5(5) . . . . ? C16 C11 N2 C10 -144.1(6) . . . . ? C12 C11 N2 C10 37.0(9) . . . . ? C2 C1 N3 C9 -4.0(10) . . . . ? C8 C9 N3 C1 -177.4(6) . . . . ? C4 C9 N3 C1 0.1(9) . . . . ? C18 C17 N4 C25 -3.9(10) . . . . ? C20 C25 N4 C17 3.4(10) . . . . ? C24 C25 N4 C17 -179.1(6) . . . . ? O2 C26 N5 C24 12.7(9) . . . . ? N6 C26 N5 C24 -169.6(5) . . . . ? C23 C24 N5 C26 88.3(8) . . . . ? C25 C24 N5 C26 -92.9(8) . . . . ? O2 C26 N6 C27 -4.0(9) . . . . ? N5 C26 N6 C27 178.3(5) . . . . ? C32 C27 N6 C26 38.8(9) . . . . ? C28 C27 N6 C26 -145.0(6) . . . . ? 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 N2 H2A O2 0.86 2.14 2.960(7) 159.0 . N1 H1A O2 0.86 2.23 3.016(7) 151.1 . N6 H6A O1 0.86 2.19 2.989(7) 154.9 1_545 N5 H5A O1 0.86 2.17 2.966(7) 154.2 1_545 N4 H4A O18 0.86 2.19 3.010(12) 159.6 1_545 N3 H3A O14 0.86 2.00 2.836(8) 164.8 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.523 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.057 # Attachment '2a.cif' data_aqphnco _database_code_depnum_ccdc_archive 'CCDC 695412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N3 O' _chemical_formula_weight 263.29 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' 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 19.5575(15) _cell_length_b 8.7354(7) _cell_length_c 17.3377(18) _cell_angle_alpha 90.00 _cell_angle_beta 113.379(5) _cell_angle_gamma 90.00 _cell_volume 2718.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1076 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17748 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.65 _reflns_number_total 4940 _reflns_number_gt 2124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0514P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4940 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.0984(2) 0.3527(5) 0.8779(3) 0.0946(15) Uani 1 1 d . . . H1 H 0.1174 0.3419 0.9360 0.113 Uiso 1 1 calc R . . C2 C 0.0327(3) 0.4370(6) 0.8391(4) 0.1106(19) Uani 1 1 d . . . H2 H 0.0094 0.4823 0.8708 0.133 Uiso 1 1 calc R . . C3 C 0.0041(3) 0.4511(5) 0.7553(5) 0.1037(17) Uani 1 1 d . . . H3 H -0.0398 0.5057 0.7284 0.124 Uiso 1 1 calc R . . C4 C 0.0398(2) 0.3842(4) 0.7077(3) 0.0724(12) Uani 1 1 d . . . C5 C 0.0135(2) 0.3929(5) 0.6194(4) 0.0926(15) Uani 1 1 d . . . H5 H -0.0296 0.4477 0.5893 0.111 Uiso 1 1 calc R . . C6 C 0.0507(2) 0.3220(5) 0.5781(3) 0.0917(14) Uani 1 1 d . . . H6 H 0.0324 0.3285 0.5198 0.110 Uiso 1 1 calc R . . C7 C 0.1164(2) 0.2391(4) 0.6214(2) 0.0708(11) Uani 1 1 d . . . H7 H 0.1402 0.1888 0.5916 0.085 Uiso 1 1 calc R . . C8 C 0.14569(18) 0.2323(4) 0.7080(2) 0.0502(9) Uani 1 1 d . . . C9 C 0.10595(19) 0.3023(4) 0.7521(3) 0.0563(10) Uani 1 1 d . . . C10 C 0.26808(19) 0.1120(4) 0.7345(2) 0.0498(8) Uani 1 1 d . . . C11 C 0.39442(18) 0.0003(4) 0.7943(2) 0.0506(9) Uani 1 1 d . . . C12 C 0.3920(2) -0.0908(4) 0.7292(3) 0.0706(11) Uani 1 1 d . . . H12 H 0.3467 -0.1112 0.6849 0.085 Uiso 1 1 calc R . . C13 C 0.4575(3) -0.1531(5) 0.7294(3) 0.0966(15) Uani 1 1 d . . . H13 H 0.4560 -0.2135 0.6846 0.116 Uiso 1 1 calc R . . C14 C 0.5242(3) -0.1259(6) 0.7952(4) 0.0963(15) Uani 1 1 d . . . H14 H 0.5676 -0.1691 0.7949 0.116 Uiso 1 1 calc R . . C15 C 0.5276(2) -0.0371(5) 0.8603(3) 0.0844(13) Uani 1 1 d . . . H15 H 0.5731 -0.0193 0.9047 0.101 Uiso 1 1 calc R . . C16 C 0.4627(2) 0.0279(4) 0.8609(3) 0.0673(11) Uani 1 1 d . . . H16 H 0.4648 0.0895 0.9055 0.081 Uiso 1 1 calc R . . C17 C 0.2401(2) 0.5653(5) 0.7526(3) 0.0754(11) Uani 1 1 d . . . H17 H 0.2601 0.5124 0.8032 0.090 Uiso 1 1 calc R . . C18 C 0.2020(2) 0.7022(5) 0.7505(3) 0.0855(13) Uani 1 1 d . . . H18 H 0.1972 0.7379 0.7986 0.103 Uiso 1 1 calc R . . C19 C 0.1726(2) 0.7815(5) 0.6780(3) 0.0767(12) Uani 1 1 d . . . H19 H 0.1468 0.8721 0.6756 0.092 Uiso 1 1 calc R . . C20 C 0.18102(19) 0.7267(4) 0.6062(3) 0.0586(10) Uani 1 1 d . . . C21 C 0.15276(19) 0.8033(5) 0.5284(3) 0.0730(11) Uani 1 1 d . . . H21 H 0.1274 0.8954 0.5228 0.088 Uiso 1 1 calc R . . C22 C 0.16265(19) 0.7423(4) 0.4613(3) 0.0730(11) Uani 1 1 d . . . H22 H 0.1445 0.7943 0.4103 0.088 Uiso 1 1 calc R . . C23 C 0.19981(18) 0.6025(4) 0.4678(2) 0.0607(10) Uani 1 1 d . . . H23 H 0.2054 0.5623 0.4210 0.073 Uiso 1 1 calc R . . C24 C 0.22783(16) 0.5250(4) 0.5421(2) 0.0473(8) Uani 1 1 d . . . C25 C 0.21946(17) 0.5878(4) 0.6135(2) 0.0515(9) Uani 1 1 d . . . C26 C 0.29333(16) 0.3122(4) 0.5046(2) 0.0470(8) Uani 1 1 d . . . C27 C 0.34950(17) 0.0647(4) 0.4899(2) 0.0509(9) Uani 1 1 d . . . C28 C 0.39342(19) 0.1140(4) 0.4494(3) 0.0687(11) Uani 1 1 d . . . H28 H 0.4026 0.2180 0.4472 0.082 Uiso 1 1 calc R . . C29 C 0.4241(2) 0.0102(5) 0.4120(3) 0.0852(13) Uani 1 1 d . . . H29 H 0.4531 0.0449 0.3842 0.102 Uiso 1 1 calc R . . C30 C 0.4119(2) -0.1427(5) 0.4158(3) 0.0855(13) Uani 1 1 d . . . H30 H 0.4321 -0.2121 0.3900 0.103 Uiso 1 1 calc R . . C31 C 0.3697(2) -0.1941(4) 0.4576(3) 0.0771(12) Uani 1 1 d . . . H31 H 0.3623 -0.2986 0.4610 0.093 Uiso 1 1 calc R . . C32 C 0.33799(18) -0.0909(4) 0.4949(2) 0.0623(10) Uani 1 1 d . . . H32 H 0.3092 -0.1260 0.5230 0.075 Uiso 1 1 calc R . . N1 N 0.13513(15) 0.2874(3) 0.8368(2) 0.0674(9) Uani 1 1 d . . . N2 N 0.21252(14) 0.1613(3) 0.75790(17) 0.0541(7) Uani 1 1 d . . . H2N H 0.2198 0.1467 0.8096 0.065 Uiso 1 1 calc R . . N3 N 0.32955(14) 0.0642(3) 0.79964(18) 0.0550(8) Uani 1 1 d . . . H3N H 0.3295 0.0732 0.8490 0.066 Uiso 1 1 calc R . . N4 N 0.24931(15) 0.5066(3) 0.68708(19) 0.0627(8) Uani 1 1 d . . . N5 N 0.26294(14) 0.3818(3) 0.55428(17) 0.0563(7) Uani 1 1 d . . . H5N H 0.2657 0.3319 0.5982 0.068 Uiso 1 1 calc R . . N6 N 0.31687(13) 0.1676(3) 0.52906(17) 0.0545(7) Uani 1 1 d . . . H6N H 0.3115 0.1344 0.5730 0.065 Uiso 1 1 calc R . . O1 O 0.26127(12) 0.1102(2) 0.66033(15) 0.0591(6) Uani 1 1 d . . . O2 O 0.29972(11) 0.3779(2) 0.44493(14) 0.0578(6) 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 0.086(3) 0.119(4) 0.091(4) -0.034(3) 0.048(3) 0.006(3) C2 0.083(4) 0.118(4) 0.141(6) -0.051(4) 0.055(4) 0.008(3) C3 0.068(3) 0.079(3) 0.161(6) -0.025(4) 0.042(4) 0.009(2) C4 0.059(3) 0.055(2) 0.100(4) 0.001(3) 0.028(3) 0.000(2) C5 0.057(3) 0.093(3) 0.114(5) 0.034(3) 0.019(3) 0.013(2) C6 0.069(3) 0.114(4) 0.083(4) 0.034(3) 0.021(3) 0.008(3) C7 0.063(3) 0.089(3) 0.056(3) 0.017(2) 0.018(2) 0.005(2) C8 0.049(2) 0.047(2) 0.055(2) 0.0070(18) 0.0218(19) -0.0011(16) C9 0.054(2) 0.044(2) 0.075(3) -0.002(2) 0.030(2) -0.0033(18) C10 0.062(2) 0.047(2) 0.048(2) 0.0039(19) 0.030(2) 0.0031(17) C11 0.060(2) 0.051(2) 0.052(2) 0.0039(18) 0.0333(19) 0.0072(18) C12 0.079(3) 0.073(3) 0.067(3) 0.000(2) 0.037(2) 0.023(2) C13 0.110(4) 0.108(4) 0.084(4) -0.005(3) 0.051(3) 0.043(3) C14 0.081(3) 0.113(4) 0.109(4) 0.018(3) 0.052(3) 0.042(3) C15 0.067(3) 0.083(3) 0.105(4) 0.005(3) 0.036(3) 0.015(2) C16 0.068(3) 0.059(2) 0.077(3) -0.003(2) 0.031(2) 0.009(2) C17 0.111(3) 0.071(3) 0.055(3) -0.015(2) 0.044(2) -0.014(2) C18 0.119(4) 0.074(3) 0.083(4) -0.029(3) 0.061(3) -0.017(3) C19 0.093(3) 0.063(3) 0.090(4) -0.016(3) 0.052(3) -0.008(2) C20 0.066(2) 0.052(2) 0.066(3) -0.019(2) 0.035(2) -0.0099(19) C21 0.077(3) 0.066(3) 0.085(3) 0.002(3) 0.042(2) 0.011(2) C22 0.080(3) 0.074(3) 0.068(3) 0.016(2) 0.033(2) 0.013(2) C23 0.072(2) 0.062(2) 0.055(2) 0.005(2) 0.032(2) 0.012(2) C24 0.050(2) 0.044(2) 0.051(2) -0.0013(18) 0.0237(17) -0.0013(16) C25 0.055(2) 0.049(2) 0.057(2) -0.0077(19) 0.0289(19) -0.0105(17) C26 0.049(2) 0.050(2) 0.045(2) -0.0022(18) 0.0213(17) -0.0039(16) C27 0.062(2) 0.050(2) 0.047(2) -0.0003(17) 0.0273(18) 0.0016(17) C28 0.084(3) 0.058(2) 0.087(3) 0.001(2) 0.057(2) 0.003(2) C29 0.100(3) 0.079(3) 0.108(4) -0.003(3) 0.074(3) 0.008(2) C30 0.095(3) 0.075(3) 0.098(4) -0.015(3) 0.050(3) 0.014(2) C31 0.095(3) 0.053(3) 0.081(3) -0.010(2) 0.033(3) 0.003(2) C32 0.079(3) 0.055(3) 0.059(2) -0.004(2) 0.034(2) -0.0052(19) N1 0.069(2) 0.070(2) 0.075(3) -0.0159(19) 0.0411(19) -0.0010(16) N2 0.0613(19) 0.0660(19) 0.0443(18) 0.0119(15) 0.0308(15) 0.0151(15) N3 0.0566(18) 0.071(2) 0.0476(18) 0.0050(15) 0.0312(15) 0.0131(15) N4 0.083(2) 0.061(2) 0.049(2) -0.0072(17) 0.0315(17) -0.0069(16) N5 0.0782(19) 0.0538(18) 0.0497(18) 0.0073(15) 0.0390(16) 0.0079(15) N6 0.076(2) 0.0500(18) 0.0490(18) 0.0038(14) 0.0369(16) 0.0048(15) O1 0.0753(16) 0.0656(15) 0.0445(15) 0.0103(13) 0.0326(13) 0.0107(12) O2 0.0746(16) 0.0607(15) 0.0497(15) 0.0079(12) 0.0368(13) 0.0024(11) _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 1.326(4) . ? C1 C2 1.400(6) . ? C2 C3 1.339(7) . ? C3 C4 1.401(6) . ? C4 C9 1.410(5) . ? C4 C5 1.411(6) . ? C5 C6 1.356(6) . ? C6 C7 1.404(5) . ? C7 C8 1.381(4) . ? C8 N2 1.394(4) . ? C8 C9 1.425(4) . ? C9 N1 1.354(4) . ? C10 O1 1.239(4) . ? C10 N3 1.348(4) . ? C10 N2 1.372(4) . ? C11 C12 1.367(4) . ? C11 C16 1.396(4) . ? C11 N3 1.422(4) . ? C12 C13 1.390(5) . ? C13 C14 1.371(6) . ? C14 C15 1.350(6) . ? C15 C16 1.395(5) . ? C17 N4 1.322(4) . ? C17 C18 1.401(5) . ? C18 C19 1.348(5) . ? C19 C20 1.403(5) . ? C20 C25 1.407(4) . ? C20 C21 1.407(5) . ? C21 C22 1.361(5) . ? C22 C23 1.403(4) . ? C23 C24 1.362(4) . ? C24 N5 1.402(4) . ? C24 C25 1.422(4) . ? C25 N4 1.371(4) . ? C26 O2 1.231(4) . ? C26 N6 1.354(4) . ? C26 N5 1.369(4) . ? C27 C28 1.376(4) . ? C27 C32 1.386(4) . ? C27 N6 1.421(4) . ? C28 C29 1.382(5) . ? C29 C30 1.363(5) . ? C30 C31 1.372(5) . ? C31 C32 1.390(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 N1 C1 C2 123.8(5) . . ? C3 C2 C1 118.6(5) . . ? C2 C3 C4 120.6(5) . . ? C3 C4 C9 117.0(5) . . ? C3 C4 C5 124.3(5) . . ? C9 C4 C5 118.6(4) . . ? C6 C5 C4 120.5(4) . . ? C5 C6 C7 121.5(4) . . ? C8 C7 C6 120.0(4) . . ? C7 C8 N2 125.2(3) . . ? C7 C8 C9 119.0(4) . . ? N2 C8 C9 115.8(3) . . ? N1 C9 C4 122.7(4) . . ? N1 C9 C8 117.1(3) . . ? C4 C9 C8 120.2(4) . . ? O1 C10 N3 123.9(3) . . ? O1 C10 N2 122.7(3) . . ? N3 C10 N2 113.4(3) . . ? C12 C11 C16 119.4(3) . . ? C12 C11 N3 122.9(3) . . ? C16 C11 N3 117.6(3) . . ? C11 C12 C13 119.7(4) . . ? C14 C13 C12 120.4(4) . . ? C15 C14 C13 120.7(4) . . ? C14 C15 C16 119.8(4) . . ? C15 C16 C11 119.9(4) . . ? N4 C17 C18 124.1(4) . . ? C19 C18 C17 119.3(4) . . ? C18 C19 C20 119.6(4) . . ? C19 C20 C25 117.5(4) . . ? C19 C20 C21 123.3(4) . . ? C25 C20 C21 119.3(4) . . ? C22 C21 C20 119.9(4) . . ? C21 C22 C23 121.1(4) . . ? C24 C23 C22 120.6(4) . . ? C23 C24 N5 125.1(3) . . ? C23 C24 C25 119.3(3) . . ? N5 C24 C25 115.6(3) . . ? N4 C25 C20 123.0(3) . . ? N4 C25 C24 117.2(3) . . ? C20 C25 C24 119.7(3) . . ? O2 C26 N6 124.3(3) . . ? O2 C26 N5 122.4(3) . . ? N6 C26 N5 113.3(3) . . ? C28 C27 C32 119.2(3) . . ? C28 C27 N6 122.4(3) . . ? C32 C27 N6 118.4(3) . . ? C27 C28 C29 120.6(3) . . ? C30 C29 C28 120.3(4) . . ? C29 C30 C31 119.9(4) . . ? C30 C31 C32 120.4(4) . . ? C27 C32 C31 119.6(3) . . ? C1 N1 C9 117.2(4) . . ? C10 N2 C8 127.9(3) . . ? C10 N3 C11 126.1(3) . . ? C17 N4 C25 116.4(3) . . ? C26 N5 C24 127.6(3) . . ? C26 N6 C27 127.0(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 N1 C1 C2 C3 1.2(7) . . . . ? C1 C2 C3 C4 -0.8(8) . . . . ? C2 C3 C4 C9 0.4(7) . . . . ? C2 C3 C4 C5 179.8(5) . . . . ? C3 C4 C5 C6 -178.6(4) . . . . ? C9 C4 C5 C6 0.8(6) . . . . ? C4 C5 C6 C7 -0.4(7) . . . . ? C5 C6 C7 C8 -1.9(6) . . . . ? C6 C7 C8 N2 -176.1(3) . . . . ? C6 C7 C8 C9 3.8(5) . . . . ? C3 C4 C9 N1 -0.3(5) . . . . ? C5 C4 C9 N1 -179.7(3) . . . . ? C3 C4 C9 C8 -179.5(3) . . . . ? C5 C4 C9 C8 1.1(5) . . . . ? C7 C8 C9 N1 177.4(3) . . . . ? N2 C8 C9 N1 -2.7(4) . . . . ? C7 C8 C9 C4 -3.4(5) . . . . ? N2 C8 C9 C4 176.5(3) . . . . ? C16 C11 C12 C13 -1.0(6) . . . . ? N3 C11 C12 C13 -178.1(3) . . . . ? C11 C12 C13 C14 1.2(7) . . . . ? C12 C13 C14 C15 -0.7(7) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C14 C15 C16 C11 0.3(6) . . . . ? C12 C11 C16 C15 0.2(5) . . . . ? N3 C11 C16 C15 177.5(3) . . . . ? N4 C17 C18 C19 -0.2(6) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? C18 C19 C20 C25 1.1(5) . . . . ? C18 C19 C20 C21 -179.3(4) . . . . ? C19 C20 C21 C22 -179.5(3) . . . . ? C25 C20 C21 C22 0.2(5) . . . . ? C20 C21 C22 C23 0.9(5) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? C22 C23 C24 N5 177.1(3) . . . . ? C22 C23 C24 C25 -0.4(5) . . . . ? C19 C20 C25 N4 -0.9(5) . . . . ? C21 C20 C25 N4 179.4(3) . . . . ? C19 C20 C25 C24 178.3(3) . . . . ? C21 C20 C25 C24 -1.4(5) . . . . ? C23 C24 C25 N4 -179.3(3) . . . . ? N5 C24 C25 N4 3.0(4) . . . . ? C23 C24 C25 C20 1.5(4) . . . . ? N5 C24 C25 C20 -176.3(3) . . . . ? C32 C27 C28 C29 1.8(6) . . . . ? N6 C27 C28 C29 -179.9(3) . . . . ? C27 C28 C29 C30 -0.9(6) . . . . ? C28 C29 C30 C31 -0.7(7) . . . . ? C29 C30 C31 C32 1.3(7) . . . . ? C28 C27 C32 C31 -1.3(5) . . . . ? N6 C27 C32 C31 -179.6(3) . . . . ? C30 C31 C32 C27 -0.3(6) . . . . ? C2 C1 N1 C9 -1.1(6) . . . . ? C4 C9 N1 C1 0.6(5) . . . . ? C8 C9 N1 C1 179.8(3) . . . . ? O1 C10 N2 C8 -8.3(5) . . . . ? N3 C10 N2 C8 172.6(3) . . . . ? C7 C8 N2 C10 13.6(5) . . . . ? C9 C8 N2 C10 -166.3(3) . . . . ? O1 C10 N3 C11 -2.2(5) . . . . ? N2 C10 N3 C11 176.8(3) . . . . ? C12 C11 N3 C10 -34.7(5) . . . . ? C16 C11 N3 C10 148.2(3) . . . . ? C18 C17 N4 C25 0.3(5) . . . . ? C20 C25 N4 C17 0.3(5) . . . . ? C24 C25 N4 C17 -179.0(3) . . . . ? O2 C26 N5 C24 7.5(5) . . . . ? N6 C26 N5 C24 -174.1(3) . . . . ? C23 C24 N5 C26 18.8(5) . . . . ? C25 C24 N5 C26 -163.6(3) . . . . ? O2 C26 N6 C27 -2.8(5) . . . . ? N5 C26 N6 C27 178.8(3) . . . . ? C28 C27 N6 C26 32.3(5) . . . . ? C32 C27 N6 C26 -149.4(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 N6 H6N O1 0.86 2.12 2.929(3) 157.2 . N5 H5N O1 0.86 2.23 3.010(3) 150.0 . N3 H3N O2 0.86 2.01 2.848(3) 162.9 4_566 N2 H2N O2 0.86 2.25 3.025(4) 149.2 4_566 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.158 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.038 # Attachment '1b.cif' data_hclo4phen _database_code_depnum_ccdc_archive 'CCDC 695413' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C96 H92 Cl6 N18 O33' _chemical_formula_weight 2238.58 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 'P2(1)/c ' 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 17.719(3) _cell_length_b 15.831(3) _cell_length_c 18.506(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.694(9) _cell_angle_gamma 90.00 _cell_volume 4972.5(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2682 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43899 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 28.26 _reflns_number_total 12099 _reflns_number_gt 5131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1082P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12099 _refine_ls_number_parameters 702 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1658 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.2215 _refine_ls_wR_factor_gt 0.1703 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _refine_ls_shift/su_max 0.003 _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 0.4483(2) 1.0209(2) 0.3803(2) 0.0621(9) Uani 1 1 d . . . H1 H 0.4933 1.0489 0.3770 0.075 Uiso 1 1 calc R . . C2 C 0.4155(2) 1.0409(2) 0.43761(19) 0.0558(9) Uani 1 1 d . . . H2 H 0.4387 1.0814 0.4735 0.067 Uiso 1 1 calc R . . C3 C 0.34847(18) 1.0002(2) 0.44077(17) 0.0491(8) Uani 1 1 d . . . H3 H 0.3263 1.0128 0.4794 0.059 Uiso 1 1 calc R . . C4 C 0.31255(18) 0.93939(19) 0.38584(16) 0.0434(7) Uani 1 1 d . . . C5 C 0.24090(19) 0.8965(2) 0.38387(18) 0.0510(8) Uani 1 1 d . . . C6 C 0.2136(2) 0.8353(2) 0.3300(2) 0.0651(10) Uani 1 1 d . . . H6 H 0.1672 0.8069 0.3284 0.078 Uiso 1 1 calc R . . C7 C 0.2538(3) 0.8147(2) 0.2777(2) 0.0721(11) Uani 1 1 d . . . H7 H 0.2348 0.7715 0.2432 0.086 Uiso 1 1 calc R . . C8 C 0.3202(2) 0.8564(2) 0.27631(19) 0.0641(10) Uani 1 1 d . . . H8 H 0.3457 0.8436 0.2402 0.077 Uiso 1 1 calc R . . C9 C 0.3495(2) 0.9188(2) 0.33019(17) 0.0497(8) Uani 1 1 d . . . C10 C 0.16836(19) 0.8660(2) 0.4755(2) 0.0543(9) Uani 1 1 d . . . C11 C 0.11678(19) 0.8629(2) 0.5858(2) 0.0568(9) Uani 1 1 d . . . C12 C 0.1418(2) 0.8919(3) 0.6586(2) 0.0696(11) Uani 1 1 d . . . H12 H 0.1777 0.9362 0.6708 0.083 Uiso 1 1 calc R . . C13 C 0.1142(2) 0.8558(3) 0.7140(2) 0.0798(12) Uani 1 1 d . . . H13 H 0.1320 0.8758 0.7632 0.096 Uiso 1 1 calc R . . C14 C 0.0610(3) 0.7913(3) 0.6973(3) 0.0816(13) Uani 1 1 d . . . H14 H 0.0421 0.7677 0.7347 0.098 Uiso 1 1 calc R . . C15 C 0.0357(2) 0.7615(3) 0.6244(3) 0.0811(12) Uani 1 1 d . . . H15 H 0.0000 0.7169 0.6128 0.097 Uiso 1 1 calc R . . C16 C 0.0630(2) 0.7974(3) 0.5681(2) 0.0716(11) Uani 1 1 d . . . H16 H 0.0452 0.7775 0.5188 0.086 Uiso 1 1 calc R . . C17 C 0.4277(2) 0.6806(2) 0.3656(2) 0.0628(10) Uani 1 1 d . . . H17 H 0.4660 0.7169 0.3580 0.075 Uiso 1 1 calc R . . C18 C 0.3982(2) 0.6922(2) 0.4266(2) 0.0634(10) Uani 1 1 d . . . H18 H 0.4168 0.7360 0.4606 0.076 Uiso 1 1 calc R . . C19 C 0.3415(2) 0.6382(2) 0.43623(18) 0.0555(9) Uani 1 1 d . . . H19 H 0.3218 0.6457 0.4773 0.067 Uiso 1 1 calc R . . C20 C 0.31236(18) 0.5717(2) 0.38541(17) 0.0455(8) Uani 1 1 d . . . C21 C 0.25159(19) 0.5140(2) 0.39121(18) 0.0518(8) Uani 1 1 d . . . C22 C 0.2278(2) 0.4519(2) 0.33705(19) 0.0578(9) Uani 1 1 d . . . H22 H 0.1878 0.4149 0.3393 0.069 Uiso 1 1 calc R . . C23 C 0.2632(2) 0.4440(2) 0.27876(19) 0.0645(10) Uani 1 1 d . . . H23 H 0.2465 0.4009 0.2437 0.077 Uiso 1 1 calc R . . C24 C 0.3208(2) 0.4967(2) 0.27136(19) 0.0607(9) Uani 1 1 d . . . H24 H 0.3437 0.4902 0.2323 0.073 Uiso 1 1 calc R . . C25 C 0.34445(19) 0.5611(2) 0.32476(18) 0.0523(8) Uani 1 1 d . . . C26 C 0.1734(2) 0.4698(2) 0.4768(2) 0.0605(9) Uani 1 1 d . . . C27 C 0.1019(2) 0.4708(2) 0.5745(2) 0.0651(10) Uani 1 1 d . . . C28 C 0.1098(3) 0.5083(3) 0.6449(3) 0.0911(15) Uani 1 1 d . . . H28 H 0.1469 0.5505 0.6631 0.109 Uiso 1 1 calc R . . C29 C 0.0613(4) 0.4813(5) 0.6866(4) 0.140(3) Uani 1 1 d . . . H29 H 0.0665 0.5051 0.7337 0.168 Uiso 1 1 calc R . . C30 C 0.0058(5) 0.4202(5) 0.6602(6) 0.167(4) Uani 1 1 d . . . H30 H -0.0267 0.4029 0.6890 0.200 Uiso 1 1 calc R . . C31 C -0.0017(3) 0.3846(4) 0.5910(4) 0.134(3) Uani 1 1 d . . . H31 H -0.0397 0.3432 0.5728 0.161 Uiso 1 1 calc R . . C32 C 0.0469(2) 0.4096(3) 0.5474(3) 0.0862(14) Uani 1 1 d . . . H32 H 0.0418 0.3850 0.5006 0.103 Uiso 1 1 calc R . . C33 C 0.4419(2) 0.3414(2) 0.3762(2) 0.0662(10) Uani 1 1 d . . . H33 H 0.4838 0.3732 0.3700 0.079 Uiso 1 1 calc R . . C34 C 0.4128(2) 0.3574(2) 0.4369(2) 0.0601(9) Uani 1 1 d . . . H34 H 0.4359 0.3982 0.4724 0.072 Uiso 1 1 calc R . . C35 C 0.34937(19) 0.3120(2) 0.44362(17) 0.0504(8) Uani 1 1 d . . . H35 H 0.3293 0.3224 0.4840 0.060 Uiso 1 1 calc R . . C36 C 0.31398(19) 0.2494(2) 0.38981(17) 0.0478(8) Uani 1 1 d . . . C37 C 0.2457(2) 0.2017(2) 0.39171(18) 0.0518(8) Uani 1 1 d . . . C38 C 0.2185(2) 0.1396(2) 0.3385(2) 0.0632(10) Uani 1 1 d . . . H38 H 0.1744 0.1081 0.3394 0.076 Uiso 1 1 calc R . . C39 C 0.2562(3) 0.1232(2) 0.2832(2) 0.0707(11) Uani 1 1 d . . . H39 H 0.2379 0.0795 0.2492 0.085 Uiso 1 1 calc R . . C40 C 0.3194(3) 0.1699(2) 0.2777(2) 0.0684(10) Uani 1 1 d . . . H40 H 0.3426 0.1598 0.2394 0.082 Uiso 1 1 calc R . . C41 C 0.3481(2) 0.2329(2) 0.33122(18) 0.0557(9) Uani 1 1 d . . . C42 C 0.17590(18) 0.1681(2) 0.4863(2) 0.0533(9) Uani 1 1 d . . . C43 C 0.11255(19) 0.1737(2) 0.5902(2) 0.0564(9) Uani 1 1 d . . . C44 C 0.1230(2) 0.2176(3) 0.6569(2) 0.0674(10) Uani 1 1 d . . . H44 H 0.1532 0.2666 0.6654 0.081 Uiso 1 1 calc R . . C45 C 0.0892(3) 0.1897(3) 0.7110(3) 0.0854(13) Uani 1 1 d . . . H45 H 0.0969 0.2196 0.7557 0.102 Uiso 1 1 calc R . . C46 C 0.0442(3) 0.1176(4) 0.6986(3) 0.0956(15) Uani 1 1 d . . . H46 H 0.0212 0.0985 0.7348 0.115 Uiso 1 1 calc R . . C47 C 0.0334(3) 0.0739(3) 0.6322(3) 0.0886(14) Uani 1 1 d . . . H47 H 0.0031 0.0250 0.6239 0.106 Uiso 1 1 calc R . . C48 C 0.0673(2) 0.1021(2) 0.5771(2) 0.0718(11) Uani 1 1 d . . . H48 H 0.0593 0.0726 0.5320 0.086 Uiso 1 1 calc R . . Cl1 Cl 0.40493(6) 0.01989(6) 0.13462(5) 0.0610(3) Uani 1 1 d . . . Cl2 Cl 0.39961(6) 0.34663(6) 0.13343(5) 0.0594(3) Uani 1 1 d . . . Cl3 Cl 0.38938(5) 0.68513(6) 0.12638(5) 0.0590(3) Uani 1 1 d . . . N1 N 0.41619(17) 0.96258(18) 0.33066(15) 0.0581(7) Uani 1 1 d . . . H1A H 0.4385 0.9511 0.2962 0.070 Uiso 1 1 calc R . . N2 N 0.20118(16) 0.92108(17) 0.43595(15) 0.0577(7) Uani 1 1 d . . . H2A H 0.1971 0.9742 0.4436 0.069 Uiso 1 1 calc R . . N3 N 0.14470(16) 0.90485(18) 0.53082(16) 0.0614(8) Uani 1 1 d . . . H3A H 0.1469 0.9591 0.5326 0.074 Uiso 1 1 calc R . . N4 N 0.40101(17) 0.6179(2) 0.31853(16) 0.0597(8) Uani 1 1 d . . . H4 H 0.4203 0.6119 0.2812 0.072 Uiso 1 1 calc R . . N5 N 0.21938(16) 0.52546(18) 0.45041(16) 0.0600(8) Uani 1 1 d . . . H5 H 0.2292 0.5731 0.4736 0.072 Uiso 1 1 calc R . . N6 N 0.15182(16) 0.50472(18) 0.53502(17) 0.0621(8) Uani 1 1 d . . . H6A H 0.1712 0.5538 0.5495 0.074 Uiso 1 1 calc R . . N7 N 0.41096(18) 0.2820(2) 0.32780(17) 0.0647(8) Uani 1 1 d . . . H7A H 0.4312 0.2731 0.2914 0.078 Uiso 1 1 calc R . . N8 N 0.20816(16) 0.22323(17) 0.44581(16) 0.0588(7) Uani 1 1 d . . . H8A H 0.2048 0.2762 0.4548 0.071 Uiso 1 1 calc R . . N9 N 0.14540(15) 0.20972(18) 0.53600(16) 0.0579(7) Uani 1 1 d . . . H9 H 0.1462 0.2640 0.5342 0.069 Uiso 1 1 calc R . . O1 O 0.16215(15) 0.79051(15) 0.46250(14) 0.0678(7) Uani 1 1 d . . . O2 O 0.15569(18) 0.39873(17) 0.45204(18) 0.0963(10) Uani 1 1 d . . . O3 O 0.17593(15) 0.09149(15) 0.47926(15) 0.0717(7) Uani 1 1 d . . . O4 O 0.38936(17) 0.77550(17) 0.12425(17) 0.0903(9) Uani 1 1 d . . . O5 O 0.31789(18) 0.6579(3) 0.1372(2) 0.1391(15) Uani 1 1 d . . . O6 O 0.45303(14) 0.65649(17) 0.18895(13) 0.0715(7) Uani 1 1 d . . . O7 O 0.4013(3) 0.6557(2) 0.06018(15) 0.1249(14) Uani 1 1 d . . . O8 O 0.39364(19) 0.43592(17) 0.12771(16) 0.0909(9) Uani 1 1 d . . . O9 O 0.32994(17) 0.3118(2) 0.14451(19) 0.1061(11) Uani 1 1 d . . . O10 O 0.46400(16) 0.32449(19) 0.19840(13) 0.0809(8) Uani 1 1 d . . . O11 O 0.4161(2) 0.3141(2) 0.06878(15) 0.1081(11) Uani 1 1 d . . . O12 O 0.4076(2) 0.1079(2) 0.1348(2) 0.1254(13) Uani 1 1 d . . . O13 O 0.33278(18) -0.0079(2) 0.1437(2) 0.1220(13) Uani 1 1 d . . . O14 O 0.46665(16) -0.0108(2) 0.19804(14) 0.0923(10) Uani 1 1 d . . . O15 O 0.4192(3) -0.0100(2) 0.06925(16) 0.1299(14) Uani 1 1 d . . . O16 O 0.2269(2) 0.6628(2) 0.5605(2) 0.0745(9) Uani 1 1 d . . . O17 O 0.2516(4) 0.3416(4) 0.5873(4) 0.112(2) Uani 0.50 1 d P . . H16A H 0.266(3) 0.671(4) 0.587(3) 0.13(3) Uiso 1 1 d . . . H16B H 0.205(2) 0.699(3) 0.534(2) 0.077(16) 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 0.062(2) 0.057(2) 0.077(3) 0.0024(19) 0.034(2) -0.0075(18) C2 0.060(2) 0.050(2) 0.058(2) -0.0030(16) 0.0181(17) -0.0026(17) C3 0.0551(19) 0.052(2) 0.0468(19) 0.0017(15) 0.0250(15) 0.0010(16) C4 0.0549(19) 0.0390(18) 0.0372(16) 0.0039(13) 0.0145(14) 0.0045(15) C5 0.057(2) 0.0413(19) 0.057(2) 0.0010(15) 0.0187(16) 0.0000(16) C6 0.068(2) 0.058(2) 0.069(2) -0.0104(19) 0.018(2) -0.0146(19) C7 0.096(3) 0.060(3) 0.058(2) -0.0164(18) 0.018(2) -0.007(2) C8 0.093(3) 0.057(2) 0.050(2) -0.0058(17) 0.033(2) -0.001(2) C9 0.061(2) 0.047(2) 0.0466(19) 0.0085(15) 0.0237(16) 0.0037(16) C10 0.050(2) 0.048(2) 0.069(2) -0.0008(17) 0.0254(17) 0.0024(16) C11 0.0429(19) 0.055(2) 0.080(3) 0.0009(19) 0.0290(18) 0.0020(16) C12 0.062(2) 0.075(3) 0.083(3) -0.014(2) 0.039(2) -0.010(2) C13 0.070(3) 0.101(4) 0.078(3) -0.016(2) 0.036(2) -0.004(3) C14 0.073(3) 0.095(4) 0.086(3) 0.020(3) 0.038(2) 0.007(3) C15 0.064(2) 0.085(3) 0.102(3) 0.009(3) 0.035(2) -0.016(2) C16 0.063(2) 0.073(3) 0.078(3) -0.001(2) 0.020(2) -0.017(2) C17 0.062(2) 0.060(2) 0.073(2) 0.011(2) 0.029(2) -0.0049(19) C18 0.067(2) 0.061(2) 0.067(2) -0.0023(18) 0.0257(19) -0.0146(19) C19 0.060(2) 0.059(2) 0.055(2) 0.0022(17) 0.0270(17) -0.0045(18) C20 0.0472(18) 0.0441(19) 0.0470(18) 0.0025(14) 0.0162(15) 0.0052(15) C21 0.0530(19) 0.050(2) 0.055(2) 0.0004(16) 0.0198(16) 0.0025(17) C22 0.055(2) 0.056(2) 0.060(2) -0.0021(18) 0.0122(17) -0.0045(17) C23 0.075(3) 0.058(2) 0.055(2) -0.0101(17) 0.0094(19) 0.007(2) C24 0.069(2) 0.066(3) 0.050(2) -0.0014(17) 0.0216(18) 0.010(2) C25 0.0527(19) 0.058(2) 0.051(2) 0.0101(16) 0.0221(16) 0.0108(17) C26 0.058(2) 0.045(2) 0.089(3) -0.0031(19) 0.039(2) -0.0049(17) C27 0.061(2) 0.051(2) 0.096(3) 0.020(2) 0.043(2) 0.0126(19) C28 0.093(3) 0.114(4) 0.088(3) 0.016(3) 0.060(3) 0.027(3) C29 0.163(6) 0.149(6) 0.153(5) 0.061(5) 0.121(5) 0.077(5) C30 0.149(6) 0.155(7) 0.263(10) 0.126(7) 0.165(7) 0.072(5) C31 0.102(4) 0.089(4) 0.252(8) 0.068(5) 0.115(5) 0.026(3) C32 0.069(3) 0.060(3) 0.146(4) 0.029(3) 0.057(3) 0.008(2) C33 0.064(2) 0.059(3) 0.080(3) 0.013(2) 0.027(2) -0.0002(19) C34 0.065(2) 0.055(2) 0.060(2) 0.0037(17) 0.0172(18) -0.0026(18) C35 0.061(2) 0.048(2) 0.0456(18) 0.0007(15) 0.0209(16) 0.0002(17) C36 0.061(2) 0.0407(18) 0.0447(18) 0.0069(14) 0.0198(16) 0.0067(16) C37 0.067(2) 0.0372(18) 0.054(2) 0.0049(15) 0.0215(17) 0.0104(16) C38 0.075(2) 0.045(2) 0.066(2) -0.0045(17) 0.015(2) -0.0022(18) C39 0.102(3) 0.052(2) 0.051(2) -0.0066(17) 0.009(2) 0.005(2) C40 0.100(3) 0.061(3) 0.049(2) -0.0006(18) 0.028(2) 0.008(2) C41 0.072(2) 0.053(2) 0.0452(19) 0.0061(16) 0.0227(17) 0.0138(19) C42 0.0488(19) 0.042(2) 0.072(2) -0.0014(17) 0.0215(17) 0.0019(16) C43 0.0451(19) 0.047(2) 0.083(3) 0.0104(18) 0.0280(18) 0.0075(16) C44 0.058(2) 0.070(3) 0.082(3) 0.000(2) 0.033(2) 0.0081(19) C45 0.077(3) 0.103(4) 0.087(3) 0.015(3) 0.041(2) 0.022(3) C46 0.084(3) 0.103(4) 0.115(4) 0.036(3) 0.054(3) 0.014(3) C47 0.076(3) 0.064(3) 0.137(4) 0.022(3) 0.049(3) -0.001(2) C48 0.068(2) 0.053(2) 0.104(3) 0.006(2) 0.042(2) 0.002(2) Cl1 0.0758(6) 0.0544(6) 0.0530(5) 0.0000(4) 0.0191(5) -0.0027(5) Cl2 0.0797(6) 0.0515(5) 0.0498(5) -0.0007(4) 0.0231(5) -0.0038(5) Cl3 0.0641(6) 0.0557(6) 0.0572(5) 0.0056(4) 0.0172(4) 0.0054(4) N1 0.0688(19) 0.0576(19) 0.0599(18) 0.0003(15) 0.0378(15) 0.0007(16) N2 0.0689(18) 0.0399(16) 0.0763(19) -0.0042(14) 0.0403(16) -0.0031(14) N3 0.0677(18) 0.0483(18) 0.081(2) -0.0022(15) 0.0418(16) -0.0071(15) N4 0.0632(18) 0.068(2) 0.0582(18) 0.0139(16) 0.0334(15) 0.0102(16) N5 0.0690(19) 0.0480(17) 0.074(2) -0.0096(14) 0.0372(16) -0.0141(14) N6 0.0675(19) 0.0480(18) 0.084(2) -0.0027(15) 0.0432(17) -0.0092(15) N7 0.076(2) 0.065(2) 0.067(2) 0.0103(16) 0.0417(17) 0.0104(17) N8 0.0689(19) 0.0402(16) 0.079(2) -0.0029(14) 0.0396(16) -0.0002(14) N9 0.0627(17) 0.0423(16) 0.079(2) -0.0003(14) 0.0365(16) 0.0023(14) O1 0.0893(18) 0.0413(15) 0.0834(17) -0.0039(13) 0.0418(14) -0.0082(13) O2 0.118(2) 0.0484(17) 0.155(3) -0.0261(17) 0.092(2) -0.0281(16) O3 0.0925(19) 0.0368(14) 0.0998(19) -0.0008(13) 0.0500(15) 0.0022(13) O4 0.0908(19) 0.0500(18) 0.128(2) 0.0004(16) 0.0291(18) 0.0088(15) O5 0.0623(19) 0.153(4) 0.193(4) 0.077(3) 0.023(2) -0.018(2) O6 0.0696(16) 0.092(2) 0.0554(15) 0.0166(13) 0.0215(13) 0.0176(14) O7 0.211(4) 0.104(3) 0.0542(17) 0.0016(16) 0.030(2) 0.054(3) O8 0.127(2) 0.0529(18) 0.108(2) 0.0058(15) 0.0578(19) 0.0088(16) O9 0.0756(19) 0.110(3) 0.130(3) 0.028(2) 0.0268(18) -0.0234(18) O10 0.0819(18) 0.111(2) 0.0513(15) 0.0097(14) 0.0220(14) 0.0041(16) O11 0.193(3) 0.084(2) 0.0567(17) -0.0131(15) 0.050(2) 0.010(2) O12 0.164(3) 0.053(2) 0.186(4) 0.000(2) 0.093(3) 0.001(2) O13 0.077(2) 0.140(3) 0.137(3) 0.037(2) 0.014(2) -0.033(2) O14 0.0793(18) 0.148(3) 0.0523(16) 0.0108(16) 0.0226(14) 0.0084(18) O15 0.214(4) 0.127(3) 0.0522(17) -0.0021(17) 0.043(2) 0.050(3) O16 0.074(2) 0.0527(19) 0.096(2) -0.0027(17) 0.0239(19) -0.0047(17) O17 0.106(5) 0.107(5) 0.120(5) -0.004(4) 0.028(4) -0.005(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 N1 1.311(4) . ? C1 C2 1.385(5) . ? C2 C3 1.366(4) . ? C3 C4 1.412(4) . ? C4 C9 1.408(4) . ? C4 C5 1.431(4) . ? C5 C6 1.375(4) . ? C5 N2 1.402(4) . ? C6 C7 1.395(5) . ? C7 C8 1.356(5) . ? C8 C9 1.394(5) . ? C9 N1 1.368(4) . ? C10 O1 1.217(4) . ? C10 N3 1.361(4) . ? C10 N2 1.371(4) . ? C11 C12 1.371(5) . ? C11 C16 1.383(5) . ? C11 N3 1.417(4) . ? C12 C13 1.380(5) . ? C13 C14 1.364(6) . ? C14 C15 1.376(6) . ? C15 C16 1.391(5) . ? C17 N4 1.317(4) . ? C17 C18 1.385(5) . ? C18 C19 1.369(4) . ? C19 C20 1.408(4) . ? C20 C25 1.406(4) . ? C20 C21 1.440(4) . ? C21 C22 1.380(4) . ? C21 N5 1.385(4) . ? C22 C23 1.401(5) . ? C23 C24 1.355(5) . ? C24 C25 1.398(5) . ? C25 N4 1.375(4) . ? C26 O2 1.221(4) . ? C26 N6 1.360(4) . ? C26 N5 1.381(4) . ? C27 C32 1.364(5) . ? C27 C28 1.402(6) . ? C27 N6 1.405(4) . ? C28 C29 1.377(7) . ? C29 C30 1.367(11) . ? C30 C31 1.371(10) . ? C31 C32 1.396(6) . ? C33 N7 1.306(5) . ? C33 C34 1.387(5) . ? C34 C35 1.369(4) . ? C35 C36 1.417(4) . ? C36 C41 1.409(4) . ? C36 C37 1.436(5) . ? C37 C38 1.377(4) . ? C37 N8 1.394(4) . ? C38 C39 1.398(5) . ? C39 C40 1.369(5) . ? C40 C41 1.395(5) . ? C41 N7 1.375(4) . ? C42 O3 1.220(4) . ? C42 N9 1.363(4) . ? C42 N8 1.378(4) . ? C43 C48 1.370(5) . ? C43 C44 1.381(5) . ? C43 N9 1.416(4) . ? C44 C45 1.378(5) . ? C45 C46 1.373(6) . ? C46 C47 1.374(6) . ? C47 C48 1.398(5) . ? Cl1 O15 1.388(3) . ? Cl1 O12 1.394(3) . ? Cl1 O13 1.407(3) . ? Cl1 O14 1.439(3) . ? Cl2 O11 1.408(3) . ? Cl2 O8 1.419(3) . ? Cl2 O9 1.419(3) . ? Cl2 O10 1.443(3) . ? Cl3 O7 1.382(3) . ? Cl3 O5 1.406(3) . ? Cl3 O4 1.431(3) . ? Cl3 O6 1.438(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 120.3(3) . . ? C3 C2 C1 119.1(3) . . ? C2 C3 C4 120.5(3) . . ? C9 C4 C3 118.5(3) . . ? C9 C4 C5 117.8(3) . . ? C3 C4 C5 123.7(3) . . ? C6 C5 N2 123.5(3) . . ? C6 C5 C4 118.5(3) . . ? N2 C5 C4 117.9(3) . . ? C5 C6 C7 121.7(3) . . ? C8 C7 C6 121.2(3) . . ? C7 C8 C9 118.5(3) . . ? N1 C9 C8 120.5(3) . . ? N1 C9 C4 117.4(3) . . ? C8 C9 C4 122.2(3) . . ? O1 C10 N3 124.2(3) . . ? O1 C10 N2 123.2(3) . . ? N3 C10 N2 112.5(3) . . ? C12 C11 C16 119.4(3) . . ? C12 C11 N3 117.9(3) . . ? C16 C11 N3 122.7(3) . . ? C11 C12 C13 120.5(4) . . ? C14 C13 C12 120.8(4) . . ? C13 C14 C15 119.3(4) . . ? C14 C15 C16 120.5(4) . . ? C11 C16 C15 119.6(4) . . ? N4 C17 C18 119.4(3) . . ? C19 C18 C17 119.1(3) . . ? C18 C19 C20 121.5(3) . . ? C25 C20 C19 117.9(3) . . ? C25 C20 C21 117.8(3) . . ? C19 C20 C21 124.3(3) . . ? C22 C21 N5 124.0(3) . . ? C22 C21 C20 118.5(3) . . ? N5 C21 C20 117.5(3) . . ? C21 C22 C23 120.8(3) . . ? C24 C23 C22 122.7(3) . . ? C23 C24 C25 117.3(3) . . ? N4 C25 C24 119.7(3) . . ? N4 C25 C20 117.4(3) . . ? C24 C25 C20 122.9(3) . . ? O2 C26 N6 124.9(3) . . ? O2 C26 N5 124.7(3) . . ? N6 C26 N5 110.5(3) . . ? C32 C27 C28 120.8(4) . . ? C32 C27 N6 124.8(4) . . ? C28 C27 N6 114.3(4) . . ? C29 C28 C27 118.5(6) . . ? C30 C29 C28 121.4(7) . . ? C29 C30 C31 119.4(6) . . ? C30 C31 C32 120.9(7) . . ? C27 C32 C31 119.0(5) . . ? N7 C33 C34 120.3(4) . . ? C35 C34 C33 119.0(3) . . ? C34 C35 C36 120.8(3) . . ? C41 C36 C35 118.0(3) . . ? C41 C36 C37 118.2(3) . . ? C35 C36 C37 123.8(3) . . ? C38 C37 N8 123.2(3) . . ? C38 C37 C36 118.8(3) . . ? N8 C37 C36 117.9(3) . . ? C37 C38 C39 120.9(4) . . ? C40 C39 C38 121.8(4) . . ? C39 C40 C41 118.2(4) . . ? N7 C41 C40 120.5(3) . . ? N7 C41 C36 117.6(3) . . ? C40 C41 C36 121.9(4) . . ? O3 C42 N9 124.5(3) . . ? O3 C42 N8 124.0(3) . . ? N9 C42 N8 111.6(3) . . ? C48 C43 C44 119.8(4) . . ? C48 C43 N9 123.0(4) . . ? C44 C43 N9 117.0(3) . . ? C45 C44 C43 120.9(4) . . ? C46 C45 C44 119.9(5) . . ? C45 C46 C47 119.5(4) . . ? C46 C47 C48 120.9(4) . . ? C43 C48 C47 119.1(4) . . ? O15 Cl1 O12 109.1(2) . . ? O15 Cl1 O13 113.4(3) . . ? O12 Cl1 O13 110.1(2) . . ? O15 Cl1 O14 108.0(2) . . ? O12 Cl1 O14 108.6(2) . . ? O13 Cl1 O14 107.48(19) . . ? O11 Cl2 O8 109.25(18) . . ? O11 Cl2 O9 112.5(2) . . ? O8 Cl2 O9 110.4(2) . . ? O11 Cl2 O10 108.20(19) . . ? O8 Cl2 O10 109.16(19) . . ? O9 Cl2 O10 107.32(18) . . ? O7 Cl3 O5 113.3(3) . . ? O7 Cl3 O4 108.2(2) . . ? O5 Cl3 O4 108.5(2) . . ? O7 Cl3 O6 108.85(19) . . ? O5 Cl3 O6 108.61(18) . . ? O4 Cl3 O6 109.34(18) . . ? C1 N1 C9 124.2(3) . . ? C10 N2 C5 124.3(3) . . ? C10 N3 C11 125.1(3) . . ? C17 N4 C25 124.7(3) . . ? C26 N5 C21 128.0(3) . . ? C26 N6 C27 128.2(3) . . ? C33 N7 C41 124.2(3) . . ? C42 N8 C37 126.4(3) . . ? C42 N9 C43 127.4(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 N1 C1 C2 C3 -1.3(5) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C9 3.1(5) . . . . ? C2 C3 C4 C5 -177.7(3) . . . . ? C9 C4 C5 C6 2.6(5) . . . . ? C3 C4 C5 C6 -176.6(3) . . . . ? C9 C4 C5 N2 -175.7(3) . . . . ? C3 C4 C5 N2 5.0(5) . . . . ? N2 C5 C6 C7 178.0(3) . . . . ? C4 C5 C6 C7 -0.3(5) . . . . ? C5 C6 C7 C8 -2.3(6) . . . . ? C6 C7 C8 C9 2.3(6) . . . . ? C7 C8 C9 N1 -179.8(3) . . . . ? C7 C8 C9 C4 0.3(5) . . . . ? C3 C4 C9 N1 -3.3(4) . . . . ? C5 C4 C9 N1 177.4(3) . . . . ? C3 C4 C9 C8 176.6(3) . . . . ? C5 C4 C9 C8 -2.7(5) . . . . ? C16 C11 C12 C13 0.4(6) . . . . ? N3 C11 C12 C13 177.4(3) . . . . ? C11 C12 C13 C14 -0.5(6) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C13 C14 C15 C16 -1.0(6) . . . . ? C12 C11 C16 C15 -0.5(6) . . . . ? N3 C11 C16 C15 -177.4(3) . . . . ? C14 C15 C16 C11 0.8(6) . . . . ? N4 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 C20 -0.3(5) . . . . ? C18 C19 C20 C25 1.2(5) . . . . ? C18 C19 C20 C21 -178.5(3) . . . . ? C25 C20 C21 C22 -0.4(5) . . . . ? C19 C20 C21 C22 179.3(3) . . . . ? C25 C20 C21 N5 -179.1(3) . . . . ? C19 C20 C21 N5 0.7(5) . . . . ? N5 C21 C22 C23 -179.9(3) . . . . ? C20 C21 C22 C23 1.5(5) . . . . ? C21 C22 C23 C24 -1.2(5) . . . . ? C22 C23 C24 C25 -0.3(5) . . . . ? C23 C24 C25 N4 -178.0(3) . . . . ? C23 C24 C25 C20 1.4(5) . . . . ? C19 C20 C25 N4 -1.4(4) . . . . ? C21 C20 C25 N4 178.4(3) . . . . ? C19 C20 C25 C24 179.2(3) . . . . ? C21 C20 C25 C24 -1.1(5) . . . . ? C32 C27 C28 C29 0.7(6) . . . . ? N6 C27 C28 C29 177.8(4) . . . . ? C27 C28 C29 C30 -0.9(8) . . . . ? C28 C29 C30 C31 0.4(10) . . . . ? C29 C30 C31 C32 0.3(10) . . . . ? C28 C27 C32 C31 -0.1(6) . . . . ? N6 C27 C32 C31 -176.8(4) . . . . ? C30 C31 C32 C27 -0.5(8) . . . . ? N7 C33 C34 C35 -2.3(5) . . . . ? C33 C34 C35 C36 0.2(5) . . . . ? C34 C35 C36 C41 2.7(5) . . . . ? C34 C35 C36 C37 -177.6(3) . . . . ? C41 C36 C37 C38 2.8(5) . . . . ? C35 C36 C37 C38 -177.0(3) . . . . ? C41 C36 C37 N8 -174.5(3) . . . . ? C35 C36 C37 N8 5.7(5) . . . . ? N8 C37 C38 C39 176.9(3) . . . . ? C36 C37 C38 C39 -0.3(5) . . . . ? C37 C38 C39 C40 -2.5(5) . . . . ? C38 C39 C40 C41 2.6(6) . . . . ? C39 C40 C41 N7 -179.4(3) . . . . ? C39 C40 C41 C36 0.0(5) . . . . ? C35 C36 C41 N7 -3.5(4) . . . . ? C37 C36 C41 N7 176.7(3) . . . . ? C35 C36 C41 C40 177.1(3) . . . . ? C37 C36 C41 C40 -2.7(5) . . . . ? C48 C43 C44 C45 0.8(5) . . . . ? N9 C43 C44 C45 176.3(3) . . . . ? C43 C44 C45 C46 -0.3(6) . . . . ? C44 C45 C46 C47 0.1(7) . . . . ? C45 C46 C47 C48 -0.3(7) . . . . ? C44 C43 C48 C47 -0.9(5) . . . . ? N9 C43 C48 C47 -176.2(3) . . . . ? C46 C47 C48 C43 0.7(6) . . . . ? C2 C1 N1 C9 1.0(5) . . . . ? C8 C9 N1 C1 -178.6(3) . . . . ? C4 C9 N1 C1 1.4(5) . . . . ? O1 C10 N2 C5 -9.2(5) . . . . ? N3 C10 N2 C5 170.0(3) . . . . ? C6 C5 N2 C10 44.7(5) . . . . ? C4 C5 N2 C10 -137.0(3) . . . . ? O1 C10 N3 C11 6.5(5) . . . . ? N2 C10 N3 C11 -172.7(3) . . . . ? C12 C11 N3 C10 138.3(4) . . . . ? C16 C11 N3 C10 -44.9(5) . . . . ? C18 C17 N4 C25 0.2(5) . . . . ? C24 C25 N4 C17 -179.8(3) . . . . ? C20 C25 N4 C17 0.7(5) . . . . ? O2 C26 N5 C21 2.3(6) . . . . ? N6 C26 N5 C21 -178.9(3) . . . . ? C22 C21 N5 C26 15.9(5) . . . . ? C20 C21 N5 C26 -165.5(3) . . . . ? O2 C26 N6 C27 -4.9(6) . . . . ? N5 C26 N6 C27 176.3(3) . . . . ? C32 C27 N6 C26 -21.8(6) . . . . ? C28 C27 N6 C26 161.3(4) . . . . ? C34 C33 N7 C41 1.4(6) . . . . ? C40 C41 N7 C33 -179.0(3) . . . . ? C36 C41 N7 C33 1.6(5) . . . . ? O3 C42 N8 C37 -0.4(5) . . . . ? N9 C42 N8 C37 178.5(3) . . . . ? C38 C37 N8 C42 41.7(5) . . . . ? C36 C37 N8 C42 -141.1(3) . . . . ? O3 C42 N9 C43 3.5(5) . . . . ? N8 C42 N9 C43 -175.4(3) . . . . ? C48 C43 N9 C42 -37.8(5) . . . . ? C44 C43 N9 C42 146.9(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 C19 H19 O16 0.93 2.60 3.499(5) 162.8 . C24 H24 O8 0.93 2.50 3.410(4) 165.8 . N9 H9 O2 0.86 2.65 3.400(4) 146.1 . N9 H9 O17 0.86 2.21 2.787(7) 123.9 . N8 H8A O17 0.86 2.57 3.130(7) 123.7 . N8 H8A O2 0.86 2.12 2.943(4) 159.7 . N7 H7A O10 0.86 2.13 2.892(4) 147.2 . N6 H6A O16 0.86 1.97 2.810(4) 165.1 . N5 H5 O16 0.86 2.15 2.956(4) 154.9 . N4 H4 O6 0.86 2.08 2.871(4) 153.2 . N1 H1A O10 0.86 2.63 3.199(4) 124.7 2_655 N1 H1A O14 0.86 2.11 2.874(4) 148.5 1_565 N2 H2A O3 0.86 2.04 2.886(4) 167.3 1_565 N3 H3A O3 0.86 2.43 3.202(4) 148.9 1_565 O16 H16A O4 0.74(5) 2.25(5) 2.946(5) 157(6) 4_576 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.385 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.081 # Attachment '3a.cif' data_8hqphnco_0m _database_code_depnum_ccdc_archive 'CCDC 697831' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2 O2' _chemical_formula_weight 264.28 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' 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' _cell_length_a 9.8403(8) _cell_length_b 10.5515(11) _cell_length_c 13.0173(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1351.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8335 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.1327 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28.47 _reflns_number_total 3326 _reflns_number_gt 1890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0689P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(2) _refine_ls_number_reflns 3326 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1830 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.9082(3) 0.4073(2) 0.3893(2) 0.0475(6) Uani 1 1 d . . . C2 C 1.0057(4) 0.4577(4) 0.3253(2) 0.0774(11) Uani 1 1 d . . . H2 H 1.0963 0.4340 0.3326 0.093 Uiso 1 1 calc R . . C3 C 0.9684(4) 0.5437(5) 0.2500(3) 0.0951(14) Uani 1 1 d . . . H3 H 1.0344 0.5765 0.2063 0.114 Uiso 1 1 calc R . . C4 C 0.8354(4) 0.5813(3) 0.2388(2) 0.0745(10) Uani 1 1 d . . . H4 H 0.8112 0.6395 0.1884 0.089 Uiso 1 1 calc R . . C5 C 0.7401(4) 0.5318(3) 0.3030(2) 0.0631(8) Uani 1 1 d . . . H5 H 0.6498 0.5565 0.2959 0.076 Uiso 1 1 calc R . . C6 C 0.7748(3) 0.4449(3) 0.3790(2) 0.0555(7) Uani 1 1 d . . . H6 H 0.7085 0.4124 0.4226 0.067 Uiso 1 1 calc R . . C7 C 0.8765(3) 0.2438(2) 0.52409(18) 0.0466(6) Uani 1 1 d . . . C8 C 0.8821(4) 0.1039(3) 0.7545(2) 0.0697(9) Uani 1 1 d . . . H8 H 0.8922 0.1833 0.7846 0.084 Uiso 1 1 calc R . . C9 C 0.9060(3) 0.0889(3) 0.6527(2) 0.0516(7) Uani 1 1 d . . . C10 C 0.8946(3) -0.0294(3) 0.6051(2) 0.0578(7) Uani 1 1 d . . . C11 C 0.9184(6) -0.1511(5) 0.4623(3) 0.125(2) Uani 1 1 d . . . H11 H 0.9435 -0.1603 0.3938 0.150 Uiso 1 1 calc R . . C12 C 0.8733(7) -0.2579(5) 0.5134(5) 0.152(3) Uani 1 1 d . . . H12 H 0.8658 -0.3345 0.4785 0.182 Uiso 1 1 calc R . . C13 C 0.8399(6) -0.2513(4) 0.6141(5) 0.1240(18) Uani 1 1 d . . . H13 H 0.8107 -0.3233 0.6489 0.149 Uiso 1 1 calc R . . C14 C 0.8500(4) -0.1335(3) 0.6662(3) 0.0758(10) Uani 1 1 d . . . C15 C 0.8267(4) -0.1138(4) 0.7710(3) 0.0904(13) Uani 1 1 d . . . H15 H 0.7996 -0.1818 0.8116 0.108 Uiso 1 1 calc R . . C16 C 0.8423(4) -0.0001(5) 0.8144(3) 0.0871(13) Uani 1 1 d . . . H16 H 0.8267 0.0101 0.8843 0.105 Uiso 1 1 calc R . . N1 N 0.9287(3) -0.0379(3) 0.50288(19) 0.0811(9) Uani 1 1 d . . . N3 N 0.9534(2) 0.3207(2) 0.46558(16) 0.0533(6) Uani 1 1 d . . . H3A H 1.0398 0.3171 0.4755 0.064 Uiso 1 1 calc R . . O1 O 0.7563(2) 0.22554(18) 0.51899(13) 0.0555(5) Uani 1 1 d . . . O2 O 0.9584(2) 0.1909(2) 0.59753(15) 0.0625(6) 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 0.0423(17) 0.0477(13) 0.0525(13) 0.0022(11) -0.0017(13) -0.0004(13) C2 0.044(2) 0.103(3) 0.085(2) 0.034(2) 0.0096(17) 0.013(2) C3 0.062(3) 0.129(3) 0.094(2) 0.056(2) 0.022(2) 0.027(2) C4 0.069(3) 0.085(2) 0.0696(18) 0.0264(17) 0.0015(18) 0.006(2) C5 0.051(2) 0.0580(16) 0.0802(18) 0.0131(14) -0.0067(17) 0.0013(16) C6 0.0413(18) 0.0521(15) 0.0730(17) 0.0096(13) 0.0006(15) -0.0009(13) C7 0.0419(19) 0.0464(13) 0.0515(14) 0.0019(12) -0.0030(13) 0.0040(13) C8 0.069(2) 0.077(2) 0.0635(17) -0.0026(15) -0.0040(16) 0.0160(19) C9 0.0385(17) 0.0582(16) 0.0581(15) 0.0128(13) -0.0046(13) -0.0014(14) C10 0.0498(18) 0.0571(17) 0.0664(17) 0.0075(14) -0.0124(15) -0.0041(14) C11 0.182(6) 0.087(3) 0.106(3) -0.031(3) -0.055(3) 0.042(3) C12 0.237(7) 0.065(3) 0.154(4) -0.029(3) -0.091(5) 0.018(4) C13 0.145(4) 0.058(2) 0.169(4) 0.022(3) -0.070(4) -0.018(3) C14 0.057(2) 0.0643(19) 0.106(3) 0.0247(18) -0.020(2) -0.0097(17) C15 0.065(3) 0.104(3) 0.102(3) 0.057(2) 0.004(2) 0.001(2) C16 0.072(3) 0.119(4) 0.070(2) 0.026(2) 0.0097(19) 0.021(3) N1 0.100(3) 0.0786(18) 0.0647(15) -0.0055(14) -0.0126(16) 0.0168(18) N3 0.0354(13) 0.0591(13) 0.0655(12) 0.0151(11) -0.0035(11) -0.0013(11) O1 0.0366(12) 0.0611(11) 0.0689(11) 0.0101(9) -0.0011(10) -0.0004(9) O2 0.0500(12) 0.0629(12) 0.0744(11) 0.0201(10) -0.0137(10) -0.0094(11) _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 1.378(4) . ? C1 C2 1.378(4) . ? C1 N3 1.421(3) . ? C2 C3 1.385(5) . ? C3 C4 1.375(5) . ? C4 C5 1.361(4) . ? C5 C6 1.392(4) . ? C7 O1 1.201(3) . ? C7 N3 1.346(3) . ? C7 O2 1.369(3) . ? C8 C9 1.355(4) . ? C8 C16 1.403(5) . ? C9 O2 1.393(3) . ? C9 C10 1.398(4) . ? C10 N1 1.375(4) . ? C10 C14 1.425(4) . ? C11 N1 1.311(5) . ? C11 C12 1.382(8) . ? C12 C13 1.354(7) . ? C13 C14 1.420(5) . ? C14 C15 1.400(5) . ? C15 C16 1.334(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 C6 C1 C2 119.6(3) . . ? C6 C1 N3 123.5(2) . . ? C2 C1 N3 116.9(3) . . ? C1 C2 C3 119.7(3) . . ? C4 C3 C2 121.1(3) . . ? C5 C4 C3 118.7(3) . . ? C4 C5 C6 121.4(3) . . ? C1 C6 C5 119.5(3) . . ? O1 C7 N3 128.3(2) . . ? O1 C7 O2 123.6(2) . . ? N3 C7 O2 108.1(2) . . ? C9 C8 C16 120.0(3) . . ? C8 C9 O2 118.5(3) . . ? C8 C9 C10 121.6(3) . . ? O2 C9 C10 119.4(2) . . ? N1 C10 C9 117.8(3) . . ? N1 C10 C14 124.4(3) . . ? C9 C10 C14 117.8(3) . . ? N1 C11 C12 125.0(5) . . ? C13 C12 C11 120.2(4) . . ? C12 C13 C14 119.3(4) . . ? C15 C14 C13 125.7(4) . . ? C15 C14 C10 118.7(3) . . ? C13 C14 C10 115.5(4) . . ? C16 C15 C14 121.8(3) . . ? C15 C16 C8 120.1(3) . . ? C11 N1 C10 115.5(4) . . ? C7 N3 C1 127.4(2) . . ? C7 O2 C9 117.2(2) . . ? 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 C3 -1.2(6) . . . . ? N3 C1 C2 C3 -179.3(4) . . . . ? C1 C2 C3 C4 0.9(7) . . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? N3 C1 C6 C5 179.0(2) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C16 C8 C9 O2 -173.7(3) . . . . ? C16 C8 C9 C10 -1.3(5) . . . . ? C8 C9 C10 N1 -176.1(3) . . . . ? O2 C9 C10 N1 -3.8(4) . . . . ? C8 C9 C10 C14 3.2(5) . . . . ? O2 C9 C10 C14 175.5(3) . . . . ? N1 C11 C12 C13 -2.3(10) . . . . ? C11 C12 C13 C14 0.9(10) . . . . ? C12 C13 C14 C15 -176.1(5) . . . . ? C12 C13 C14 C10 0.6(7) . . . . ? N1 C10 C14 C15 176.0(3) . . . . ? C9 C10 C14 C15 -3.2(5) . . . . ? N1 C10 C14 C13 -0.9(5) . . . . ? C9 C10 C14 C13 179.9(4) . . . . ? C13 C14 C15 C16 178.0(4) . . . . ? C10 C14 C15 C16 1.5(6) . . . . ? C14 C15 C16 C8 0.5(7) . . . . ? C9 C8 C16 C15 -0.6(6) . . . . ? C12 C11 N1 C10 1.9(8) . . . . ? C9 C10 N1 C11 179.0(4) . . . . ? C14 C10 N1 C11 -0.3(5) . . . . ? O1 C7 N3 C1 6.0(4) . . . . ? O2 C7 N3 C1 -171.0(2) . . . . ? C6 C1 N3 C7 14.5(4) . . . . ? C2 C1 N3 C7 -167.5(3) . . . . ? O1 C7 O2 C9 15.8(4) . . . . ? N3 C7 O2 C9 -167.1(2) . . . . ? C8 C9 O2 C7 -113.8(3) . . . . ? C10 C9 O2 C7 73.7(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 C6 H6 O1 0.93 2.38 2.951(3) 119.1 . N3 H3A O1 0.86 2.18 3.027(3) 168.6 4_556 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.47 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.174 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 # Attachment '3b.cif' data_8hqphncohclo4_0m _database_code_depnum_ccdc_archive 'CCDC 697986' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 Cl2 N4 O13' _chemical_formula_weight 747.48 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.428(2) _cell_length_b 13.936(4) _cell_length_c 17.274(5) _cell_angle_alpha 108.989(5) _cell_angle_beta 93.671(5) _cell_angle_gamma 97.095(5) _cell_volume 1667.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 534 _cell_measurement_theta_min 3.90 _cell_measurement_theta_max 20.15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11187 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.2040 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 28.36 _reflns_number_total 7980 _reflns_number_gt 2489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0689P] 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 7980 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2752 _refine_ls_R_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.331 _refine_ls_restrained_S_all 1.331 _refine_ls_shift/su_max 0.007 _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 0.3540(9) 0.9358(6) 0.2836(4) 0.0719(18) Uani 1 1 d . . . H1A H 0.3619 0.9001 0.2284 0.086 Uiso 1 1 calc R . . C2 C 0.4310(8) 1.0379(5) 0.3173(4) 0.0690(17) Uani 1 1 d . . . H2 H 0.4929 1.0707 0.2855 0.083 Uiso 1 1 calc R . . C3 C 0.4152(7) 1.0893(4) 0.3966(4) 0.0600(16) Uani 1 1 d . . . H3A H 0.4641 1.1585 0.4192 0.072 Uiso 1 1 calc R . . C4 C 0.3274(7) 1.0410(4) 0.4457(3) 0.0472(13) Uani 1 1 d . . . C5 C 0.3118(7) 1.0899(4) 0.5296(3) 0.0561(15) Uani 1 1 d . . . H5 H 0.3591 1.1590 0.5545 0.067 Uiso 1 1 calc R . . C6 C 0.2289(8) 1.0376(4) 0.5746(3) 0.0611(16) Uani 1 1 d . . . H6 H 0.2196 1.0709 0.6300 0.073 Uiso 1 1 calc R . . C7 C 0.1567(7) 0.9330(4) 0.5375(3) 0.0561(15) Uani 1 1 d . . . H7 H 0.1004 0.8973 0.5687 0.067 Uiso 1 1 calc R . . C8 C 0.1687(7) 0.8833(4) 0.4558(3) 0.0511(14) Uani 1 1 d . . . C9 C 0.2539(7) 0.9356(4) 0.4099(3) 0.0453(13) Uani 1 1 d . . . C10 C 0.1699(9) 0.7076(4) 0.4330(3) 0.0609(16) Uani 1 1 d . . . C11 C 0.0955(10) 0.5193(4) 0.3966(3) 0.0637(16) Uani 1 1 d . . . C12 C -0.0492(9) 0.4421(5) 0.3775(3) 0.0784(19) Uani 1 1 d . . . H12 H -0.1657 0.4553 0.3657 0.094 Uiso 1 1 calc R . . C13 C -0.0254(13) 0.3455(5) 0.3752(4) 0.099(2) Uani 1 1 d . . . H13 H -0.1254 0.2936 0.3620 0.118 Uiso 1 1 calc R . . C14 C 0.1439(16) 0.3251(6) 0.3922(5) 0.119(3) Uani 1 1 d . . . H14 H 0.1606 0.2595 0.3906 0.142 Uiso 1 1 calc R . . C15 C 0.2877(12) 0.4012(6) 0.4115(5) 0.121(3) Uani 1 1 d . . . H15 H 0.4030 0.3874 0.4244 0.146 Uiso 1 1 calc R . . C16 C 0.2680(11) 0.5007(5) 0.4125(4) 0.100(2) Uani 1 1 d . . . H16 H 0.3686 0.5519 0.4237 0.120 Uiso 1 1 calc R . . C17 C 0.4405(8) 0.2644(5) -0.0769(3) 0.0658(17) Uani 1 1 d . . . H17 H 0.4127 0.2480 -0.1334 0.079 Uiso 1 1 calc R . . C18 C 0.5334(8) 0.3596(5) -0.0304(4) 0.0705(18) Uani 1 1 d . . . H18 H 0.5683 0.4081 -0.0550 0.085 Uiso 1 1 calc R . . C19 C 0.5734(8) 0.3819(4) 0.0515(4) 0.0680(17) Uani 1 1 d . . . H19 H 0.6387 0.4458 0.0825 0.082 Uiso 1 1 calc R . . C20 C 0.5191(7) 0.3110(4) 0.0915(4) 0.0586(15) Uani 1 1 d . . . C21 C 0.5509(9) 0.3304(5) 0.1761(4) 0.0732(18) Uani 1 1 d . . . H21 H 0.6115 0.3938 0.2107 0.088 Uiso 1 1 calc R . . C22 C 0.4929(10) 0.2563(5) 0.2072(4) 0.090(2) Uani 1 1 d . . . H22 H 0.5168 0.2689 0.2634 0.108 Uiso 1 1 calc R . . C23 C 0.3987(9) 0.1619(4) 0.1574(4) 0.0708(18) Uani 1 1 d . . . H23 H 0.3565 0.1133 0.1808 0.085 Uiso 1 1 calc R . . C24 C 0.3675(7) 0.1397(4) 0.0750(3) 0.0516(14) Uani 1 1 d . . . C25 C 0.4271(7) 0.2153(4) 0.0417(3) 0.0468(13) Uani 1 1 d . . . C26 C 0.2579(8) -0.0431(4) 0.0300(4) 0.0548(15) Uani 1 1 d . . . C27 C 0.0695(7) -0.2117(4) -0.0436(4) 0.0516(14) Uani 1 1 d . . . C28 C 0.0527(8) -0.2473(4) 0.0219(4) 0.0648(16) Uani 1 1 d . . . H28 H 0.0929 -0.2041 0.0755 0.078 Uiso 1 1 calc R . . C29 C -0.0247(8) -0.3479(5) 0.0067(4) 0.0705(17) Uani 1 1 d . . . H29 H -0.0376 -0.3721 0.0506 0.085 Uiso 1 1 calc R . . C30 C -0.0827(8) -0.4126(5) -0.0717(5) 0.080(2) Uani 1 1 d . . . H30 H -0.1311 -0.4808 -0.0815 0.096 Uiso 1 1 calc R . . C31 C -0.0682(9) -0.3750(5) -0.1355(4) 0.0804(19) Uani 1 1 d . . . H31 H -0.1108 -0.4184 -0.1887 0.096 Uiso 1 1 calc R . . C32 C 0.0062(8) -0.2766(5) -0.1238(3) 0.0641(16) Uani 1 1 d . . . H32 H 0.0149 -0.2529 -0.1681 0.077 Uiso 1 1 calc R . . Cl1 Cl 0.6222(3) 0.63856(12) 0.26046(11) 0.0725(5) Uani 1 1 d . . . Cl2 Cl 0.8922(2) 0.01500(14) 0.21608(10) 0.0678(5) Uani 1 1 d . . . N1 N 0.2699(6) 0.8886(3) 0.3287(3) 0.0563(12) Uani 1 1 d . . . H1 H 0.2227 0.8251 0.3059 0.068 Uiso 1 1 calc R . . N2 N 0.0601(6) 0.6171(3) 0.3975(3) 0.0677(14) Uani 1 1 d . . . H2A H -0.0429 0.6189 0.3727 0.081 Uiso 1 1 calc R . . N3 N 0.3910(6) 0.1962(3) -0.0408(3) 0.0561(12) Uani 1 1 d . . . H3 H 0.3332 0.1370 -0.0709 0.067 Uiso 1 1 calc R . . N4 N 0.1390(6) -0.1090(3) -0.0333(3) 0.0590(12) Uani 1 1 d . . . H4 H 0.1024 -0.0857 -0.0710 0.071 Uiso 1 1 calc R . . O1 O 0.0857(5) 0.7827(3) 0.4166(2) 0.0671(11) Uani 1 1 d . . . O2 O 0.2703(5) 0.0517(3) 0.0184(2) 0.0662(11) Uani 1 1 d . . . O3 O 0.6667(7) 0.6207(4) 0.3341(3) 0.1199(17) Uani 1 1 d . . . O4 O 0.4565(6) 0.5781(3) 0.2172(3) 0.0997(15) Uani 1 1 d . . . O5 O 0.7603(7) 0.6112(4) 0.2078(3) 0.1305(19) Uani 1 1 d . . . O6 O 0.6089(7) 0.7431(3) 0.2771(3) 0.1151(17) Uani 1 1 d . . . O7 O 0.9958(8) 0.0216(4) 0.1537(3) 0.152(2) Uani 1 1 d . . . O8 O 0.7400(10) -0.0416(6) 0.1924(4) 0.262(5) Uani 1 1 d . . . O9 O 0.8651(17) 0.0943(6) 0.2654(7) 0.399(10) Uani 1 1 d . . . O10 O 0.9746(14) -0.0195(15) 0.2585(8) 0.442(12) Uani 1 1 d . . . O12 O 0.3157(6) 0.7230(3) 0.4709(3) 0.0830(13) Uani 1 1 d . . . O13 O 0.3382(5) -0.0586(3) 0.0854(2) 0.0692(11) Uani 1 1 d . . . O11 O 0.1521(6) 0.6924(4) 0.2231(3) 0.0893(16) Uiso 1 1 d . . . H11B H 0.044(10) 0.694(5) 0.225(4) 0.134 Uiso 1 1 d . . . H11A H 0.163(10) 0.654(5) 0.253(4) 0.134 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 0.064(5) 0.098(5) 0.053(4) 0.021(4) 0.006(3) 0.021(4) C2 0.058(4) 0.091(5) 0.069(5) 0.045(4) 0.001(3) 0.006(4) C3 0.058(4) 0.054(4) 0.071(4) 0.029(4) -0.007(3) 0.005(3) C4 0.049(4) 0.045(3) 0.048(3) 0.018(3) -0.002(3) 0.005(3) C5 0.053(4) 0.043(3) 0.062(4) 0.004(3) -0.006(3) 0.011(3) C6 0.064(4) 0.060(4) 0.055(4) 0.013(3) 0.006(3) 0.013(3) C7 0.055(4) 0.052(4) 0.061(4) 0.024(3) -0.001(3) 0.003(3) C8 0.056(4) 0.043(3) 0.047(4) 0.010(3) -0.005(3) -0.001(3) C9 0.045(4) 0.049(3) 0.040(3) 0.014(3) 0.000(3) 0.008(3) C10 0.067(5) 0.049(4) 0.064(4) 0.017(3) 0.008(3) 0.003(4) C11 0.080(5) 0.044(4) 0.058(4) 0.012(3) -0.001(3) -0.004(4) C12 0.075(5) 0.058(4) 0.094(5) 0.028(4) -0.016(4) -0.011(4) C13 0.114(7) 0.050(5) 0.123(6) 0.032(4) -0.008(5) -0.016(5) C14 0.135(9) 0.068(6) 0.148(8) 0.031(5) 0.007(6) 0.016(6) C15 0.101(7) 0.073(6) 0.178(8) 0.027(6) -0.008(6) 0.023(5) C16 0.083(6) 0.058(5) 0.151(7) 0.027(4) -0.005(5) 0.010(4) C17 0.087(5) 0.059(4) 0.056(4) 0.021(4) 0.022(3) 0.018(4) C18 0.082(5) 0.056(4) 0.072(5) 0.018(4) 0.018(4) 0.011(4) C19 0.059(4) 0.045(4) 0.087(5) 0.007(4) 0.004(3) 0.005(3) C20 0.046(4) 0.056(4) 0.077(5) 0.024(4) 0.007(3) 0.016(3) C21 0.083(5) 0.052(4) 0.069(5) 0.002(3) -0.016(3) 0.014(3) C22 0.126(7) 0.072(5) 0.065(5) 0.019(4) -0.014(4) 0.008(5) C23 0.095(5) 0.050(4) 0.070(4) 0.025(3) -0.006(4) 0.012(4) C24 0.056(4) 0.043(3) 0.052(4) 0.012(3) -0.004(3) 0.007(3) C25 0.044(4) 0.049(4) 0.047(3) 0.011(3) 0.002(3) 0.019(3) C26 0.053(4) 0.057(4) 0.056(4) 0.020(3) 0.012(3) 0.010(3) C27 0.057(4) 0.037(3) 0.064(4) 0.021(3) 0.012(3) 0.007(3) C28 0.066(4) 0.057(4) 0.069(4) 0.018(3) 0.009(3) 0.008(3) C29 0.065(5) 0.068(4) 0.091(5) 0.044(4) 0.014(4) 0.004(4) C30 0.075(5) 0.054(4) 0.112(6) 0.035(5) 0.015(4) -0.007(3) C31 0.069(5) 0.068(5) 0.092(5) 0.018(4) 0.004(4) -0.007(4) C32 0.070(4) 0.066(4) 0.056(4) 0.021(3) 0.009(3) 0.005(3) Cl1 0.0789(13) 0.0516(10) 0.0750(12) 0.0113(9) -0.0106(10) 0.0030(9) Cl2 0.0648(12) 0.0786(12) 0.0552(10) 0.0215(9) -0.0002(9) -0.0007(9) N1 0.061(3) 0.057(3) 0.049(3) 0.016(3) 0.003(2) 0.010(2) N2 0.074(4) 0.035(3) 0.082(3) 0.015(2) -0.020(3) -0.007(3) N3 0.066(3) 0.039(3) 0.059(3) 0.011(2) 0.007(2) 0.006(2) N4 0.071(3) 0.054(3) 0.057(3) 0.028(3) 0.004(2) 0.004(3) O1 0.073(3) 0.044(2) 0.076(3) 0.020(2) -0.017(2) -0.007(2) O2 0.091(3) 0.044(2) 0.059(2) 0.020(2) -0.009(2) -0.007(2) O3 0.111(4) 0.147(4) 0.118(4) 0.080(3) -0.023(3) 0.000(3) O4 0.080(3) 0.063(3) 0.124(4) -0.001(2) -0.034(3) 0.004(2) O5 0.091(4) 0.117(4) 0.134(4) -0.020(3) 0.031(3) -0.006(3) O6 0.182(5) 0.047(3) 0.103(4) 0.014(2) -0.020(3) 0.014(3) O7 0.190(6) 0.218(6) 0.119(4) 0.113(4) 0.104(4) 0.095(5) O8 0.137(7) 0.286(9) 0.182(6) -0.122(6) 0.049(5) -0.102(6) O9 0.469(18) 0.149(6) 0.375(13) -0.152(8) 0.315(13) -0.186(8) O10 0.170(9) 1.04(3) 0.435(15) 0.60(2) 0.142(9) 0.268(15) O12 0.056(3) 0.050(2) 0.128(4) 0.017(2) -0.021(2) 0.006(2) O13 0.075(3) 0.055(2) 0.074(3) 0.020(2) -0.006(2) 0.010(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 N1 1.314(7) . ? C1 C2 1.381(7) . ? C2 C3 1.345(7) . ? C3 C4 1.389(7) . ? C4 C5 1.406(6) . ? C4 C9 1.416(6) . ? C5 C6 1.353(6) . ? C6 C7 1.407(6) . ? C7 C8 1.369(6) . ? C8 C9 1.373(6) . ? C8 O1 1.386(5) . ? C9 N1 1.362(6) . ? C10 O12 1.186(6) . ? C10 N2 1.346(6) . ? C10 O1 1.377(6) . ? C11 C12 1.364(7) . ? C11 C16 1.367(8) . ? C11 N2 1.414(6) . ? C12 C13 1.368(8) . ? C13 C14 1.357(10) . ? C14 C15 1.349(10) . ? C15 C16 1.407(8) . ? C17 N3 1.325(6) . ? C17 C18 1.375(7) . ? C18 C19 1.349(7) . ? C19 C20 1.413(7) . ? C20 C25 1.393(7) . ? C20 C21 1.395(7) . ? C21 C22 1.350(7) . ? C22 C23 1.386(7) . ? C23 C24 1.352(6) . ? C24 O2 1.376(5) . ? C24 C25 1.395(6) . ? C25 N3 1.364(5) . ? C26 O13 1.187(6) . ? C26 N4 1.357(6) . ? C26 O2 1.394(6) . ? C27 C28 1.382(7) . ? C27 C32 1.398(6) . ? C27 N4 1.410(6) . ? C28 C29 1.382(7) . ? C29 C30 1.366(7) . ? C30 C31 1.371(7) . ? C31 C32 1.359(7) . ? Cl1 O3 1.402(4) . ? Cl1 O6 1.408(4) . ? Cl1 O4 1.414(4) . ? Cl1 O5 1.420(5) . ? Cl2 O10 1.178(8) . ? Cl2 O9 1.205(7) . ? Cl2 O8 1.257(6) . ? Cl2 O7 1.384(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.7(6) . . ? C3 C2 C1 119.1(6) . . ? C2 C3 C4 121.3(5) . . ? C3 C4 C5 123.8(5) . . ? C3 C4 C9 118.3(5) . . ? C5 C4 C9 117.9(5) . . ? C6 C5 C4 120.9(5) . . ? C5 C6 C7 120.0(5) . . ? C8 C7 C6 120.5(5) . . ? C7 C8 C9 119.8(5) . . ? C7 C8 O1 121.3(5) . . ? C9 C8 O1 118.8(5) . . ? N1 C9 C8 121.5(5) . . ? N1 C9 C4 117.6(5) . . ? C8 C9 C4 120.9(5) . . ? O12 C10 N2 127.7(6) . . ? O12 C10 O1 124.2(5) . . ? N2 C10 O1 108.1(5) . . ? C12 C11 C16 120.2(6) . . ? C12 C11 N2 117.7(6) . . ? C16 C11 N2 122.1(6) . . ? C11 C12 C13 121.0(7) . . ? C14 C13 C12 120.2(7) . . ? C15 C14 C13 119.3(8) . . ? C14 C15 C16 121.9(8) . . ? C11 C16 C15 117.5(7) . . ? N3 C17 C18 119.6(5) . . ? C19 C18 C17 119.4(6) . . ? C18 C19 C20 122.0(5) . . ? C25 C20 C21 118.5(5) . . ? C25 C20 C19 116.6(6) . . ? C21 C20 C19 124.9(6) . . ? C22 C21 C20 119.5(6) . . ? C21 C22 C23 121.5(6) . . ? C24 C23 C22 120.7(6) . . ? C23 C24 O2 127.4(5) . . ? C23 C24 C25 118.5(5) . . ? O2 C24 C25 114.0(5) . . ? N3 C25 C20 119.2(5) . . ? N3 C25 C24 119.6(5) . . ? C20 C25 C24 121.2(5) . . ? O13 C26 N4 129.6(6) . . ? O13 C26 O2 124.7(5) . . ? N4 C26 O2 105.8(5) . . ? C28 C27 C32 120.2(5) . . ? C28 C27 N4 122.7(5) . . ? C32 C27 N4 117.0(5) . . ? C27 C28 C29 119.1(5) . . ? C30 C29 C28 121.1(6) . . ? C29 C30 C31 118.8(6) . . ? C32 C31 C30 122.3(6) . . ? C31 C32 C27 118.5(5) . . ? O3 Cl1 O6 109.9(3) . . ? O3 Cl1 O4 112.2(3) . . ? O6 Cl1 O4 109.3(3) . . ? O3 Cl1 O5 109.3(4) . . ? O6 Cl1 O5 109.4(3) . . ? O4 Cl1 O5 106.7(3) . . ? O10 Cl2 O9 101.3(10) . . ? O10 Cl2 O8 106.8(9) . . ? O9 Cl2 O8 106.7(6) . . ? O10 Cl2 O7 108.2(6) . . ? O9 Cl2 O7 117.5(5) . . ? O8 Cl2 O7 115.0(4) . . ? C1 N1 C9 123.0(5) . . ? C10 N2 C11 127.2(5) . . ? C17 N3 C25 123.2(5) . . ? C26 N4 C27 126.6(5) . . ? C10 O1 C8 116.6(4) . . ? C24 O2 C26 122.2(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 N1 C1 C2 C3 -1.5(8) . . . . ? C1 C2 C3 C4 1.7(8) . . . . ? C2 C3 C4 C5 177.9(5) . . . . ? C2 C3 C4 C9 -0.1(7) . . . . ? C3 C4 C5 C6 -178.1(5) . . . . ? C9 C4 C5 C6 -0.1(7) . . . . ? C4 C5 C6 C7 0.0(8) . . . . ? C5 C6 C7 C8 -0.3(8) . . . . ? C6 C7 C8 C9 0.9(7) . . . . ? C6 C7 C8 O1 -174.7(4) . . . . ? C7 C8 C9 N1 179.5(5) . . . . ? O1 C8 C9 N1 -4.8(7) . . . . ? C7 C8 C9 C4 -1.0(7) . . . . ? O1 C8 C9 C4 174.7(4) . . . . ? C3 C4 C9 N1 -1.7(6) . . . . ? C5 C4 C9 N1 -179.8(4) . . . . ? C3 C4 C9 C8 178.7(5) . . . . ? C5 C4 C9 C8 0.6(7) . . . . ? C16 C11 C12 C13 1.1(9) . . . . ? N2 C11 C12 C13 179.9(6) . . . . ? C11 C12 C13 C14 0.0(11) . . . . ? C12 C13 C14 C15 0.2(12) . . . . ? C13 C14 C15 C16 -1.5(13) . . . . ? C12 C11 C16 C15 -2.4(10) . . . . ? N2 C11 C16 C15 178.9(6) . . . . ? C14 C15 C16 C11 2.7(11) . . . . ? N3 C17 C18 C19 0.3(8) . . . . ? C17 C18 C19 C20 -1.4(8) . . . . ? C18 C19 C20 C25 2.1(8) . . . . ? C18 C19 C20 C21 -177.9(5) . . . . ? C25 C20 C21 C22 0.3(8) . . . . ? C19 C20 C21 C22 -179.8(6) . . . . ? C20 C21 C22 C23 -1.5(9) . . . . ? C21 C22 C23 C24 2.4(10) . . . . ? C22 C23 C24 O2 -177.1(6) . . . . ? C22 C23 C24 C25 -2.1(8) . . . . ? C21 C20 C25 N3 178.3(4) . . . . ? C19 C20 C25 N3 -1.6(7) . . . . ? C21 C20 C25 C24 -0.1(7) . . . . ? C19 C20 C25 C24 180.0(5) . . . . ? C23 C24 C25 N3 -177.5(4) . . . . ? O2 C24 C25 N3 -1.8(6) . . . . ? C23 C24 C25 C20 0.9(7) . . . . ? O2 C24 C25 C20 176.6(4) . . . . ? C32 C27 C28 C29 1.0(8) . . . . ? N4 C27 C28 C29 177.0(5) . . . . ? C27 C28 C29 C30 0.7(8) . . . . ? C28 C29 C30 C31 -2.1(9) . . . . ? C29 C30 C31 C32 1.8(9) . . . . ? C30 C31 C32 C27 -0.2(9) . . . . ? C28 C27 C32 C31 -1.2(8) . . . . ? N4 C27 C32 C31 -177.5(5) . . . . ? C2 C1 N1 C9 -0.4(8) . . . . ? C8 C9 N1 C1 -178.5(5) . . . . ? C4 C9 N1 C1 2.0(7) . . . . ? O12 C10 N2 C11 -1.0(10) . . . . ? O1 C10 N2 C11 177.8(5) . . . . ? C12 C11 N2 C10 162.6(5) . . . . ? C16 C11 N2 C10 -18.6(9) . . . . ? C18 C17 N3 C25 0.1(8) . . . . ? C20 C25 N3 C17 0.6(7) . . . . ? C24 C25 N3 C17 179.0(5) . . . . ? O13 C26 N4 C27 6.4(10) . . . . ? O2 C26 N4 C27 -173.4(4) . . . . ? C28 C27 N4 C26 26.9(8) . . . . ? C32 C27 N4 C26 -156.9(5) . . . . ? O12 C10 O1 C8 -8.1(8) . . . . ? N2 C10 O1 C8 173.1(4) . . . . ? C7 C8 O1 C10 -75.7(6) . . . . ? C9 C8 O1 C10 108.6(5) . . . . ? C23 C24 O2 C26 -29.3(8) . . . . ? C25 C24 O2 C26 155.5(4) . . . . ? O13 C26 O2 C24 -5.5(8) . . . . ? N4 C26 O2 C24 174.4(4) . . . . ? 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 N4 H4 O7 0.86 2.06 2.914(6) 175.2 2_655 N1 H1 O11 0.86 1.92 2.743(6) 160.1 . O11 H11B O5 0.81(8) 2.22(7) 2.952(7) 150(6) 1_455 N2 H2A O3 0.86 2.22 3.067(7) 167.1 1_455 N3 H3 O8 0.86 2.08 2.816(7) 143.1 2_655 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.752 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.066