data_General _audit_creation_date 2012-09-19 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'ENTER NAME' _publ_contact_author_email 'ENTER EMAIL ADDRESS' _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'ENTER JOURNAL NAME HERE' _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, D. Siliqi, R. Spagna (2007) SIR2008 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_User-defined #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H16 Cl2 N4 O2' _chemical_formula_moiety 'C20 H16 Cl2 N4 O2' _chemical_formula_weight 415.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '+X,+Y,+Z' 2 '-X,-Y,-Z' #------------------------------------------------------------------------------ _cell_length_a 7.7965(11) _cell_length_b 11.0035(13) _cell_length_c 12.2289(17) _cell_angle_alpha 70.789(8) _cell_angle_beta 89.602(7) _cell_angle_gamma 85.231(7) _cell_volume 987.0(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2881 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 26.27 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.040 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428.00 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.336 _exptl_absorpt_correction_T_max 0.986 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 8181 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3995 _reflns_number_gt 1476 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.2135 _refine_ls_number_restraints 32 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3995 _refine_ls_number_parameters 254 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1101P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.400 _refine_diff_density_min -0.380 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'N' 'N' 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'O' 'O' 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'Cl' 'Cl' 0.1484 0.1585 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Cl1 Cl 0.55703(18) 0.31653(13) 0.96274(10) 0.0932(6) Uani 1.0 2 d . . . Cl2 Cl 0.3184(3) -0.10807(13) 0.42278(14) 0.1275(7) Uani 1.0 2 d . . . O1 O -0.1631(5) 0.8901(3) 0.0296(3) 0.0955(12) Uani 1.0 2 d . . . O2 O -0.1090(5) 0.9113(3) 0.1999(3) 0.0874(11) Uani 1.0 2 d . . . N1 N 0.2203(5) 0.5580(3) 0.5007(3) 0.0597(10) Uani 1.0 2 d . . . N2 N 0.2204(5) 0.4874(3) 0.4379(3) 0.0576(9) Uani 1.0 2 d . . . N3 N 0.0721(5) 0.5073(3) 0.1514(3) 0.0591(10) Uani 1.0 2 d . . . N4 N -0.0518(6) 0.6697(4) -0.0034(3) 0.0823(13) Uani 1.0 2 d . . . C1 C 0.3072(6) 0.4954(4) 0.6096(4) 0.0575(11) Uani 1.0 2 d . . . C2 C 0.3068(6) 0.5628(4) 0.6862(4) 0.0673(12) Uani 1.0 2 d . . . C3 C 0.3822(6) 0.5094(5) 0.7948(4) 0.0702(13) Uani 1.0 2 d . . . C4 C 0.4620(6) 0.3866(5) 0.8264(4) 0.0655(12) Uani 1.0 2 d . . . C5 C 0.4648(6) 0.3173(4) 0.7502(4) 0.0694(13) Uani 1.0 2 d . . . C6 C 0.3889(6) 0.3708(4) 0.6424(4) 0.0670(13) Uani 1.0 2 d . . . C7 C 0.1375(6) 0.5434(4) 0.3290(4) 0.0569(11) Uani 1.0 2 d . . . C8 C 0.1323(5) 0.4636(4) 0.2603(4) 0.0544(11) Uani 1.0 2 d . . . C9 C 0.0033(6) 0.6319(4) 0.1061(4) 0.0614(12) Uani 1.0 2 d . . . C10 C -0.0083(6) 0.7154(4) 0.1736(4) 0.0594(11) Uani 1.0 2 d . . . C11 C 0.0639(6) 0.6700(4) 0.2835(4) 0.0618(12) Uani 1.0 2 d . . . C12 C 0.1882(6) 0.3229(4) 0.3039(4) 0.0550(11) Uani 1.0 2 d . . . C13 C 0.1366(6) 0.2439(4) 0.4115(4) 0.0641(11) Uani 1.0 2 d . . . C14 C 0.1770(7) 0.1142(4) 0.4471(4) 0.0752(13) Uani 1.0 2 d . . . C15 C 0.2715(7) 0.0589(5) 0.3781(5) 0.0765(13) Uani 1.0 2 d . . . C16 C 0.3236(7) 0.1342(5) 0.2713(4) 0.0781(14) Uani 1.0 2 d . . . C17 C 0.2835(6) 0.2664(4) 0.2353(4) 0.0639(12) Uani 1.0 2 d . . . C18 C -0.0993(7) 0.8460(4) 0.1251(4) 0.0713(13) Uani 1.0 2 d . . . C19 C -0.2044(9) 1.0397(5) 0.1505(5) 0.114(3) Uani 1.0 2 d . . . C20 C -0.1920(9) 1.1084(5) 0.2368(4) 0.116(2) Uani 1.0 2 d . . . H2 H 0.2544 0.6466 0.6641 0.0808 Uiso 1.0 2 calc R . . H3 H 0.3790 0.5559 0.8461 0.0843 Uiso 1.0 2 calc R . . H4A H -0.0430 0.6165 -0.0416 0.0988 Uiso 1.0 2 calc R . . H4B H -0.0964 0.7474 -0.0361 0.0988 Uiso 1.0 2 calc R . . H5 H 0.5185 0.2339 0.7723 0.0833 Uiso 1.0 2 calc R . . H6 H 0.3919 0.3241 0.5913 0.0804 Uiso 1.0 2 calc R . . H11 H 0.0636 0.7244 0.3278 0.0742 Uiso 1.0 2 calc R . . H13 H 0.0738 0.2806 0.4594 0.0769 Uiso 1.0 2 calc R . . H14 H 0.1404 0.0627 0.5187 0.0903 Uiso 1.0 2 calc R . . H16 H 0.3852 0.0965 0.2236 0.0937 Uiso 1.0 2 calc R . . H17 H 0.3213 0.3177 0.1641 0.0767 Uiso 1.0 2 calc R . . H19A H -0.3240 1.0305 0.1359 0.1367 Uiso 1.0 2 calc R . . H19B H -0.1546 1.0881 0.0780 0.1367 Uiso 1.0 2 calc R . . H20A H -0.2541 1.0655 0.3047 0.1387 Uiso 1.0 2 calc R . . H20B H -0.2407 1.1960 0.2036 0.1387 Uiso 1.0 2 calc R . . H20C H -0.0733 1.1079 0.2575 0.1387 Uiso 1.0 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0946(11) 0.1212(12) 0.0560(7) 0.0068(8) -0.0191(7) -0.0219(7) Cl2 0.1785(18) 0.0637(9) 0.1337(14) 0.0245(9) -0.0170(12) -0.0314(9) O1 0.134(4) 0.075(3) 0.069(3) 0.021(2) -0.026(3) -0.0181(18) O2 0.119(3) 0.064(2) 0.079(2) 0.0166(18) -0.011(2) -0.0292(18) N1 0.073(3) 0.061(2) 0.049(2) -0.0026(17) -0.0044(18) -0.0236(18) N2 0.066(3) 0.064(3) 0.0483(19) -0.0055(17) -0.0074(17) -0.0263(18) N3 0.078(3) 0.060(3) 0.0403(18) -0.0031(18) -0.0060(18) -0.0172(16) N4 0.134(4) 0.063(3) 0.049(2) 0.006(3) -0.024(3) -0.0193(18) C1 0.067(3) 0.059(3) 0.052(3) -0.003(2) -0.005(2) -0.026(2) C2 0.080(4) 0.065(3) 0.064(3) 0.001(3) -0.009(3) -0.032(3) C3 0.080(4) 0.082(4) 0.060(3) -0.005(3) -0.012(3) -0.038(3) C4 0.069(4) 0.080(4) 0.044(3) -0.008(3) -0.003(3) -0.016(3) C5 0.080(4) 0.064(3) 0.064(3) 0.006(3) -0.008(3) -0.023(3) C6 0.077(4) 0.079(4) 0.055(3) 0.001(3) -0.013(3) -0.038(3) C7 0.068(3) 0.062(3) 0.046(3) -0.007(2) -0.004(2) -0.024(2) C8 0.056(3) 0.059(3) 0.051(3) -0.003(2) -0.004(2) -0.022(2) C9 0.075(4) 0.061(3) 0.047(3) -0.004(3) -0.003(3) -0.017(2) C10 0.072(3) 0.054(3) 0.053(3) -0.003(2) -0.004(3) -0.019(2) C11 0.073(4) 0.061(3) 0.058(3) -0.007(3) 0.005(3) -0.027(3) C12 0.060(3) 0.061(3) 0.047(2) -0.003(2) -0.012(2) -0.0228(19) C13 0.086(3) 0.060(3) 0.052(3) -0.001(2) -0.007(3) -0.0255(19) C14 0.102(4) 0.059(3) 0.062(3) 0.000(3) -0.012(3) -0.017(2) C15 0.088(4) 0.058(3) 0.081(3) 0.011(3) -0.021(3) -0.023(3) C16 0.085(4) 0.078(4) 0.084(3) 0.011(3) -0.005(3) -0.047(3) C17 0.070(4) 0.074(3) 0.055(3) -0.001(3) -0.001(3) -0.033(3) C18 0.092(4) 0.059(3) 0.066(3) 0.000(3) -0.003(3) -0.025(3) C19 0.170(7) 0.069(4) 0.095(4) 0.036(4) -0.011(4) -0.028(3) C20 0.164(6) 0.086(4) 0.090(4) 0.029(4) -0.024(4) -0.029(4) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl1 C4 1.732(4) yes . . Cl2 C15 1.743(5) yes . . O1 C18 1.201(6) yes . . O2 C18 1.335(7) yes . . O2 C19 1.478(6) yes . . N1 N2 1.259(6) yes . . N1 C1 1.427(5) yes . . N2 C7 1.406(5) yes . . N3 C8 1.332(5) yes . . N3 C9 1.363(5) yes . . N4 C9 1.327(5) yes . . C1 C2 1.373(7) yes . . C1 C6 1.394(6) yes . . C2 C3 1.377(6) yes . . C3 C4 1.371(7) yes . . C4 C5 1.384(8) yes . . C5 C6 1.370(6) yes . . C7 C8 1.404(7) yes . . C7 C11 1.394(6) yes . . C8 C12 1.489(6) yes . . C9 C10 1.421(7) yes . . C10 C11 1.376(6) yes . . C10 C18 1.481(6) yes . . C12 C13 1.395(5) yes . . C12 C17 1.379(7) yes . . C13 C14 1.357(6) yes . . C14 C15 1.372(8) yes . . C15 C16 1.376(7) yes . . C16 C17 1.382(7) yes . . C19 C20 1.494(9) yes . . N4 H4A 0.860 no . . N4 H4B 0.860 no . . C2 H2 0.930 no . . C3 H3 0.930 no . . C5 H5 0.930 no . . C6 H6 0.930 no . . C11 H11 0.930 no . . C13 H13 0.930 no . . C14 H14 0.930 no . . C16 H16 0.930 no . . C17 H17 0.930 no . . C19 H19A 0.970 no . . C19 H19B 0.970 no . . C20 H20A 0.960 no . . C20 H20B 0.960 no . . C20 H20C 0.960 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C18 O2 C19 112.2(4) yes . . . N2 N1 C1 113.0(4) yes . . . N1 N2 C7 116.0(4) yes . . . C8 N3 C9 119.4(4) yes . . . N1 C1 C2 117.1(4) yes . . . N1 C1 C6 124.0(5) yes . . . C2 C1 C6 118.9(4) yes . . . C1 C2 C3 121.6(4) yes . . . C2 C3 C4 119.1(5) yes . . . Cl1 C4 C3 120.2(4) yes . . . Cl1 C4 C5 119.6(4) yes . . . C3 C4 C5 120.2(4) yes . . . C4 C5 C6 120.4(4) yes . . . C1 C6 C5 119.8(5) yes . . . N2 C7 C8 116.1(4) yes . . . N2 C7 C11 125.9(5) yes . . . C8 C7 C11 117.9(4) yes . . . N3 C8 C7 122.5(4) yes . . . N3 C8 C12 114.5(4) yes . . . C7 C8 C12 123.0(4) yes . . . N3 C9 N4 116.3(4) yes . . . N3 C9 C10 121.2(4) yes . . . N4 C9 C10 122.5(4) yes . . . C9 C10 C11 118.0(4) yes . . . C9 C10 C18 119.5(4) yes . . . C11 C10 C18 122.5(5) yes . . . C7 C11 C10 120.7(5) yes . . . C8 C12 C13 121.1(4) yes . . . C8 C12 C17 120.4(4) yes . . . C13 C12 C17 118.4(4) yes . . . C12 C13 C14 120.9(5) yes . . . C13 C14 C15 120.3(4) yes . . . Cl2 C15 C14 120.0(4) yes . . . Cl2 C15 C16 119.7(5) yes . . . C14 C15 C16 120.2(4) yes . . . C15 C16 C17 119.5(5) yes . . . C12 C17 C16 120.7(4) yes . . . O1 C18 O2 121.9(4) yes . . . O1 C18 C10 124.8(5) yes . . . O2 C18 C10 113.2(4) yes . . . O2 C19 C20 107.4(4) yes . . . C9 N4 H4A 120.000 no . . . C9 N4 H4B 120.004 no . . . H4A N4 H4B 119.997 no . . . C1 C2 H2 119.216 no . . . C3 C2 H2 119.209 no . . . C2 C3 H3 120.436 no . . . C4 C3 H3 120.433 no . . . C4 C5 H5 119.807 no . . . C6 C5 H5 119.816 no . . . C1 C6 H6 120.083 no . . . C5 C6 H6 120.084 no . . . C7 C11 H11 119.669 no . . . C10 C11 H11 119.671 no . . . C12 C13 H13 119.567 no . . . C14 C13 H13 119.561 no . . . C13 C14 H14 119.868 no . . . C15 C14 H14 119.868 no . . . C15 C16 H16 120.250 no . . . C17 C16 H16 120.242 no . . . C12 C17 H17 119.639 no . . . C16 C17 H17 119.640 no . . . O2 C19 H19A 110.241 no . . . O2 C19 H19B 110.241 no . . . C20 C19 H19A 110.239 no . . . C20 C19 H19B 110.240 no . . . H19A C19 H19B 108.517 no . . . C19 C20 H20A 109.473 no . . . C19 C20 H20B 109.471 no . . . C19 C20 H20C 109.473 no . . . H20A C20 H20B 109.474 no . . . H20A C20 H20C 109.468 no . . . H20B C20 H20C 109.468 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C18 O2 C19 C20 -174.5(4) no . . . . C19 O2 C18 O1 -0.2(7) no . . . . C19 O2 C18 C10 -178.4(4) no . . . . N2 N1 C1 C2 -177.0(3) no . . . . N2 N1 C1 C6 2.0(6) no . . . . C1 N1 N2 C7 -179.7(3) no . . . . N1 N2 C7 C8 -178.0(3) no . . . . N1 N2 C7 C11 3.2(6) no . . . . C8 N3 C9 N4 179.0(4) no . . . . C8 N3 C9 C10 -1.2(6) no . . . . C9 N3 C8 C7 -4.0(6) no . . . . C9 N3 C8 C12 174.2(4) no . . . . N1 C1 C2 C3 177.9(4) no . . . . N1 C1 C6 C5 -178.1(4) no . . . . C2 C1 C6 C5 0.9(6) no . . . . C6 C1 C2 C3 -1.2(7) no . . . . C1 C2 C3 C4 1.1(7) no . . . . C2 C3 C4 Cl1 -179.7(4) no . . . . C2 C3 C4 C5 -0.7(7) no . . . . Cl1 C4 C5 C6 179.4(3) no . . . . C3 C4 C5 C6 0.4(7) no . . . . C4 C5 C6 C1 -0.5(7) no . . . . N2 C7 C8 N3 -173.7(4) no . . . . N2 C7 C8 C12 8.3(6) no . . . . N2 C7 C11 C10 177.5(4) no . . . . C8 C7 C11 C10 -1.2(6) no . . . . C11 C7 C8 N3 5.2(6) no . . . . C11 C7 C8 C12 -172.8(4) no . . . . N3 C8 C12 C13 -132.4(4) no . . . . N3 C8 C12 C17 43.5(5) no . . . . C7 C8 C12 C13 45.8(6) no . . . . C7 C8 C12 C17 -138.3(4) no . . . . N3 C9 C10 C11 4.9(6) no . . . . N3 C9 C10 C18 -174.0(4) no . . . . N4 C9 C10 C11 -175.3(4) no . . . . N4 C9 C10 C18 5.8(7) no . . . . C9 C10 C11 C7 -3.5(6) no . . . . C9 C10 C18 O1 -1.7(7) no . . . . C9 C10 C18 O2 176.4(4) no . . . . C11 C10 C18 O1 179.4(5) no . . . . C11 C10 C18 O2 -2.4(7) no . . . . C18 C10 C11 C7 175.3(4) no . . . . C8 C12 C13 C14 175.0(4) no . . . . C8 C12 C17 C16 -174.5(4) no . . . . C13 C12 C17 C16 1.4(7) no . . . . C17 C12 C13 C14 -1.0(7) no . . . . C12 C13 C14 C15 0.8(7) no . . . . C13 C14 C15 Cl2 -178.4(4) no . . . . C13 C14 C15 C16 -1.1(8) no . . . . Cl2 C15 C16 C17 178.9(4) no . . . . C14 C15 C16 C17 1.6(8) no . . . . C15 C16 C17 C12 -1.7(8) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N4 2.661(6) no . . O1 C9 2.878(5) no . . O1 C19 2.552(7) no . . O2 C11 2.748(5) no . . N1 C8 3.514(6) no . . N1 C11 2.775(5) no . . N2 C2 3.484(7) no . . N2 C6 2.699(5) no . . N2 C12 2.839(6) no . . N2 C13 2.928(6) no . . N3 C11 2.776(7) no . . N3 C13 3.533(5) no . . N3 C17 2.882(5) no . . N4 C8 3.509(5) no . . N4 C18 2.871(7) no . . C1 C4 2.764(6) no . . C1 C7 3.544(6) no . . C2 C5 2.738(6) no . . C3 C6 2.767(8) no . . C7 C9 2.756(6) no . . C7 C13 3.113(6) no . . C8 C10 2.754(6) no . . C12 C15 2.765(6) no . . C13 C16 2.749(7) no . . C14 C17 2.748(6) no . . Cl1 C9 3.571(5) no . 2_666 Cl1 C19 3.539(5) no . 1_646 O1 O1 3.562(6) no . 2_575 O1 C19 3.581(7) no . 2_575 N1 N2 3.553(5) no . 2_566 N1 C6 3.518(6) no . 2_666 N1 C7 3.503(6) no . 2_566 N2 N1 3.553(5) no . 2_566 N2 C6 3.524(6) no . 2_666 N3 N4 3.077(6) no . 2_565 N3 C2 3.544(6) no . 2_566 N4 N3 3.077(6) no . 2_565 N4 C17 3.217(6) no . 2_565 C1 C7 3.573(6) no . 2_566 C1 C11 3.557(6) no . 2_566 C2 N3 3.544(6) no . 2_566 C2 C8 3.499(6) no . 2_566 C3 C9 3.522(7) no . 2_566 C5 C7 3.560(7) no . 2_666 C5 C18 3.558(7) no . 2_566 C6 N1 3.518(6) no . 2_666 C6 N2 3.524(6) no . 2_666 C7 N1 3.503(6) no . 2_566 C7 C1 3.573(6) no . 2_566 C7 C5 3.560(7) no . 2_666 C8 C2 3.499(6) no . 2_566 C9 Cl1 3.571(5) no . 2_666 C9 C3 3.522(7) no . 2_566 C11 C1 3.557(6) no . 2_566 C17 N4 3.217(6) no . 2_565 C18 C5 3.558(7) no . 2_566 C19 Cl1 3.539(5) no . 1_464 C19 O1 3.581(7) no . 2_575 Cl1 H3 2.8010 no . . Cl1 H5 2.7904 no . . Cl2 H14 2.7976 no . . Cl2 H16 2.7997 no . . O1 H4A 3.4558 no . . O1 H4B 2.0164 no . . O1 H19A 2.5749 no . . O1 H19B 2.4445 no . . O2 H11 2.4373 no . . O2 H20A 2.6257 no . . O2 H20B 3.2296 no . . O2 H20C 2.5219 no . . N1 H2 2.5197 no . . N1 H6 2.6856 no . . N1 H11 2.5360 no . . N1 H13 3.5327 no . . N2 H6 2.4402 no . . N2 H11 2.6995 no . . N2 H13 2.5673 no . . N3 H4A 2.4091 no . . N3 H4B 3.0728 no . . N3 H17 2.6956 no . . C1 H3 3.2364 no . . C1 H5 3.2319 no . . C2 H6 3.2237 no . . C3 H5 3.2253 no . . C4 H2 3.2064 no . . C4 H6 3.2294 no . . C5 H3 3.2309 no . . C6 H2 3.2216 no . . C7 H13 2.8885 no . . C8 H11 3.2407 no . . C8 H13 2.6648 no . . C8 H17 2.6377 no . . C9 H11 3.2436 no . . C10 H4A 3.1826 no . . C10 H4B 2.5609 no . . C12 H14 3.2323 no . . C12 H16 3.2375 no . . C13 H6 3.3470 no . . C13 H17 3.2251 no . . C14 H16 3.2221 no . . C15 H13 3.2038 no . . C15 H17 3.2209 no . . C16 H14 3.2204 no . . C17 H13 3.2223 no . . C18 H4B 2.5416 no . . C18 H11 2.6699 no . . C18 H19A 2.6062 no . . C18 H19B 2.5337 no . . H2 H3 2.3022 no . . H5 H6 2.2985 no . . H6 H13 3.1212 no . . H13 H14 2.2795 no . . H16 H17 2.3109 no . . H19A H20A 2.2976 no . . H19A H20B 2.3703 no . . H19A H20C 2.8111 no . . H19B H20A 2.8110 no . . H19B H20B 2.2965 no . . H19B H20C 2.3716 no . . Cl1 H3 3.1585 no . 2_667 Cl1 H17 3.0652 no . 1_556 Cl1 H19A 3.2259 no . 1_646 Cl1 H19B 3.1828 no . 1_646 Cl1 H20B 3.1729 no . 1_646 Cl2 H2 3.3477 no . 1_545 Cl2 H5 3.3267 no . 2_656 Cl2 H6 3.1864 no . 2_656 Cl2 H11 3.2774 no . 1_545 Cl2 H20A 3.5413 no . 2_566 O1 H16 3.5130 no . 2_565 O1 H19B 2.7873 no . 2_575 O2 H14 3.5516 no . 2_566 N1 H6 3.4256 no . 2_666 N1 H13 2.9209 no . 2_566 N3 H2 3.5437 no . 2_566 N3 H4A 2.2283 no . 2_565 N3 H4B 3.5198 no . 2_565 N4 H4A 3.0406 no . 2_565 N4 H17 2.8504 no . 2_565 N4 H19B 3.1010 no . 2_575 N4 H20B 3.3884 no . 2_575 N4 H20C 3.4564 no . 2_575 C2 H13 3.4853 no . 2_566 C2 H20B 3.3532 no . 2_576 C3 H17 3.2549 no . 2_666 C3 H20B 3.3426 no . 2_576 C8 H2 3.3530 no . 2_566 C8 H4A 3.1765 no . 2_565 C9 H4A 3.0758 no . 2_565 C9 H19B 3.4575 no . 2_575 C10 H19B 3.4316 no . 2_575 C11 H5 3.4998 no . 2_666 C11 H13 3.5094 no . 2_566 C12 H2 3.4709 no . 2_566 C12 H4A 3.2454 no . 2_565 C12 H20C 3.4324 no . 1_545 C13 H2 3.2086 no . 2_566 C13 H20C 3.2823 no . 1_545 C14 H14 3.2155 no . 2_556 C14 H20A 3.0591 no . 2_566 C14 H20C 3.0636 no . 1_545 C15 H20C 2.9973 no . 1_545 C16 H4B 3.2140 no . 2_565 C16 H19A 3.5000 no . 1_645 C16 H20A 3.3144 no . 1_645 C16 H20B 3.5588 no . 1_645 C16 H20C 3.1425 no . 1_545 C17 H3 3.3579 no . 2_666 C17 H4A 2.9050 no . 2_565 C17 H4B 2.9018 no . 2_565 C17 H20C 3.3675 no . 1_545 C18 H5 3.5670 no . 2_566 C18 H19B 3.0976 no . 2_575 C19 H4B 3.4137 no . 2_575 C19 H16 3.3792 no . 1_465 C20 H2 3.3009 no . 2_576 C20 H4B 3.3985 no . 2_575 C20 H14 2.9726 no . 2_566 C20 H16 3.3166 no . 1_465 H2 Cl2 3.3477 no . 1_565 H2 N3 3.5437 no . 2_566 H2 C8 3.3530 no . 2_566 H2 C12 3.4709 no . 2_566 H2 C13 3.2086 no . 2_566 H2 C20 3.3009 no . 2_576 H2 H13 2.8958 no . 2_566 H2 H20A 3.3130 no . 2_576 H2 H20B 2.7274 no . 2_576 H2 H20C 3.3559 no . 2_576 H3 Cl1 3.1585 no . 2_667 H3 C17 3.3579 no . 2_666 H3 H17 2.7985 no . 2_666 H3 H20B 2.7225 no . 2_576 H4A N3 2.2283 no . 2_565 H4A N4 3.0406 no . 2_565 H4A C8 3.1765 no . 2_565 H4A C9 3.0758 no . 2_565 H4A C12 3.2454 no . 2_565 H4A C17 2.9050 no . 2_565 H4A H4A 2.4625 no . 2_565 H4A H17 2.5580 no . 2_565 H4A H20B 3.3291 no . 2_575 H4A H20C 3.4850 no . 2_575 H4B N3 3.5198 no . 2_565 H4B C16 3.2140 no . 2_565 H4B C17 2.9018 no . 2_565 H4B C19 3.4137 no . 2_575 H4B C20 3.3985 no . 2_575 H4B H16 3.1811 no . 2_565 H4B H17 2.6506 no . 2_565 H4B H19B 2.7072 no . 2_575 H4B H20B 3.2935 no . 2_575 H4B H20C 3.0131 no . 2_575 H5 Cl2 3.3267 no . 2_656 H5 C11 3.4998 no . 2_666 H5 C18 3.5670 no . 2_566 H5 H11 3.4849 no . 2_666 H5 H19A 3.2535 no . 2_566 H6 Cl2 3.1864 no . 2_656 H6 N1 3.4256 no . 2_666 H11 Cl2 3.2774 no . 1_565 H11 H5 3.4849 no . 2_666 H11 H13 2.7930 no . 2_566 H13 N1 2.9209 no . 2_566 H13 C2 3.4853 no . 2_566 H13 C11 3.5094 no . 2_566 H13 H2 2.8958 no . 2_566 H13 H11 2.7930 no . 2_566 H14 O2 3.5516 no . 2_566 H14 C14 3.2155 no . 2_556 H14 C20 2.9726 no . 2_566 H14 H14 2.7995 no . 2_556 H14 H20A 2.2919 no . 2_566 H14 H20C 3.4812 no . 1_545 H14 H20C 2.8379 no . 2_566 H16 O1 3.5130 no . 2_565 H16 C19 3.3792 no . 1_645 H16 C20 3.3166 no . 1_645 H16 H4B 3.1811 no . 2_565 H16 H19A 2.6498 no . 1_645 H16 H20A 2.9438 no . 1_645 H16 H20B 3.1798 no . 1_645 H16 H20C 3.5926 no . 1_545 H17 Cl1 3.0652 no . 1_554 H17 N4 2.8504 no . 2_565 H17 C3 3.2549 no . 2_666 H17 H3 2.7985 no . 2_666 H17 H4A 2.5580 no . 2_565 H17 H4B 2.6506 no . 2_565 H17 H20B 3.5392 no . 1_645 H19A Cl1 3.2259 no . 1_464 H19A C16 3.5000 no . 1_465 H19A H5 3.2535 no . 2_566 H19A H16 2.6498 no . 1_465 H19B Cl1 3.1828 no . 1_464 H19B O1 2.7873 no . 2_575 H19B N4 3.1010 no . 2_575 H19B C9 3.4575 no . 2_575 H19B C10 3.4316 no . 2_575 H19B C18 3.0976 no . 2_575 H19B H4B 2.7072 no . 2_575 H20A Cl2 3.5413 no . 2_566 H20A C14 3.0591 no . 2_566 H20A C16 3.3144 no . 1_465 H20A H2 3.3130 no . 2_576 H20A H14 2.2919 no . 2_566 H20A H16 2.9438 no . 1_465 H20B Cl1 3.1729 no . 1_464 H20B N4 3.3884 no . 2_575 H20B C2 3.3532 no . 2_576 H20B C3 3.3426 no . 2_576 H20B C16 3.5588 no . 1_465 H20B H2 2.7274 no . 2_576 H20B H3 2.7225 no . 2_576 H20B H4A 3.3291 no . 2_575 H20B H4B 3.2935 no . 2_575 H20B H16 3.1798 no . 1_465 H20B H17 3.5392 no . 1_465 H20C N4 3.4564 no . 2_575 H20C C12 3.4324 no . 1_565 H20C C13 3.2823 no . 1_565 H20C C14 3.0636 no . 1_565 H20C C15 2.9973 no . 1_565 H20C C16 3.1425 no . 1_565 H20C C17 3.3675 no . 1_565 H20C H2 3.3559 no . 2_576 H20C H4A 3.4850 no . 2_575 H20C H4B 3.0131 no . 2_575 H20C H14 3.4812 no . 1_565 H20C H14 2.8379 no . 2_566 H20C H16 3.5926 no . 1_565 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N4 H4A N3 . . 2_565 3.077(6) 0.860 2.228 169.0 no N4 H4B O1 . . . 2.661(6) 0.860 2.016 131.1 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================