# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email ANTONIO.HOZ@UCLM.ES _publ_contact_author_name 'Prof Antonio de la Hoz' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_method Xtal3.6 _audit_creation_date 02-09-28 _audit_update_record ? _publ_contact_author_address ; Organic Chemistry Universidad de Castilla-La Mancha Facultad de Química Universidad de Castilla-La Mancha Campus Universitario Ciudad Real 13071 SPAIN ; _publ_section_title ; Synthesis, Structural Determination and Dynamic Behavior of 2-Chloro-4,6-bis(pyrazolylamino)-1,3,5-triazines ; loop_ _publ_author_name 'A.de la Hoz' A.Diaz-Ortiz 'Jose Elguero' C.Foces-Foces 'Andres Moreno' ; S.Moreno ; A.Sanchez-Migallon 'Gema Valiente' data_g34 _database_code_CSD 197194 # 2. EXPERIMENTAL DATA #--------------------- _chemical_formula_sum 'C21 H16 CL1 N9' _chemical_formula_moiety 'C21 H16 CL1 N9' _chemical_formula_weight 429.88 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P_2yn loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 8.0587(8) _cell_length_b 11.2534(11) _cell_length_c 22.104(3) _cell_angle_alpha 90 _cell_angle_beta 98.529(13) _cell_angle_gamma 90 _cell_volume 1982.4(4) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.44 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _diffrn_radiation_type 'Cu K\\a' _diffrn_radiation_wavelength 1.54178 _cell_measurement_reflns_used 74 _cell_measurement_theta_min 2 _cell_measurement_theta_max 35 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu 1.956 _exptl_crystal_description octahedral _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.33 _exptl_crystal_size_rad ? _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Four circle diffractometer' _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North el al.,1968)' _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 1.203 _diffrn_reflns_number 3374 _reflns_number_total 3002 _reflns_Friedel_coverage ? _reflns_number_gt 2480 _reflns_threshold_expression 'I > 2.00 sig(I )' _diffrn_reflns_theta_max 66.94 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents .053 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 100 _diffrn_standards_decay_% none _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .043 _refine_ls_wR_factor_ref .055 _refine_ls_goodness_of_fit_ref .972 _refine_ls_number_reflns 2480 _refine_ls_number_parameters 281 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]' _refine_ls_hydrogen_treatment noref _refine_ls_shift/su_max .001 _refine_diff_density_min -.271 _refine_diff_density_max .336 _refine_ls_extinction_method '(Zachariasen, 1967)' _refine_ls_extinction_coef 3690(309) _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Seifert XRD3000-S, 1996' _computing_cell_refinement 'LSUCRE (Appleman, 1984)' _computing_data_reduction 'xtal ADDREF DIFDAT ABSCAL SORTRF' _computing_structure_solution xtal _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 84 .017 .009 'INTERNATIONAL TABLES FOR X-RAY=' H ? 0 64 0 0 'INTERNATIONAL TABLES FOR X-RAY=' N ? 0 36 .029 .018 'INTERNATIONAL TABLES FOR X-RAY=' CL ? 0 4 .348 .702 'INTERNATIONAL TABLES FOR X-RAY=' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group CL1 .94156(9) .85254(6) .57694(3) .0529(4) Uani ? ? 1.00000 ? ? N1 .8514(3) .63889(18) .54163(10) .0435(12) Uani ? ? 1.00000 ? ? C2 .7635(3) .5664(2) .49948(12) .0401(13) Uani ? ? 1.00000 ? ? N3 .6698(3) .60060(19) .44787(10) .0413(11) Uani ? ? 1.00000 ? ? C4 .6683(3) .7183(2) .43846(11) .0399(13) Uani ? ? 1.00000 ? ? N5 .7482(3) .79980(18) .47705(10) .0435(12) Uani ? ? 1.00000 ? ? C6 .8336(3) .7515(2) .52571(11) .0402(13) Uani ? ? 1.00000 ? ? N7a .8332(3) .22337(19) .57300(10) .0447(11) Uani ? ? 1.00000 ? ? N8a .9594(3) .2998(2) .59572(11) .0518(13) Uani ? ? 1.00000 ? ? C9a 1.0164(4) .2593(3) .65063(14) .0565(17) Uani ? ? 1.00000 ? ? C10a .9318(4) .1572(3) .66491(16) .0621(18) Uani ? ? 1.00000 ? ? C11a .8146(4) .1372(2) .61430(15) .0558(16) Uani ? ? 1.00000 ? ? C12a .7415(3) .2355(2) .51334(13) .0451(14) Uani ? ? 1.00000 ? ? C13a .7133(3) .3468(2) .48389(13) .0454(14) Uani ? ? 1.00000 ? ? C14a .6171(4) .3492(3) .42607(14) .0584(17) Uani ? ? 1.00000 ? ? C15a .5519(4) .2443(3) .39813(15) .068(2) Uani ? ? 1.00000 ? ? C16a .5827(4) .1362(3) .42692(16) .065(2) Uani ? ? 1.00000 ? ? C17a .6784(4) .1318(3) .48357(15) .0578(17) Uani ? ? 1.00000 ? ? N18a .7807(3) .44867(18) .51446(10) .0457(12) Uani ? ? 1.00000 ? ? N7b .5754(3) .8514(2) .26455(10) .0455(12) Uani ? ? 1.00000 ? ? N8b .6077(3) .9438(2) .30464(10) .0528(13) Uani ? ? 1.00000 ? ? C9b .7028(4) 1.0176(3) .27713(16) .0637(18) Uani ? ? 1.00000 ? ? C10b .7298(4) .9748(3) .22059(17) .070(2) Uani ? ? 1.00000 ? ? C11b .6472(4) .8689(3) .21349(14) .0595(18) Uani ? ? 1.00000 ? ? C12b .4753(3) .7527(2) .27811(11) .0422(13) Uani ? ? 1.00000 ? ? C13b .4857(3) .7070(2) .33721(12) .0402(13) Uani ? ? 1.00000 ? ? C14b .3880(3) .6075(3) .34631(13) .0491(15) Uani ? ? 1.00000 ? ? C15b .2848(3) .5564(3) .29738(15) .0569(17) Uani ? ? 1.00000 ? ? C16b .2741(4) .6033(3) .23954(15) .0609(18) Uani ? ? 1.00000 ? ? C17b .3687(4) .7030(3) .22980(13) .0549(16) Uani ? ? 1.00000 ? ? N18b .5857(3) .76429(19) .38603(10) .0438(11) Uani ? ? 1.00000 ? ? H9a 1.11579 .29915 .68100 .06000 Uiso ? ? 1.00000 ? ? H10a .95040 .10700 .70588 .06600 Uiso ? ? 1.00000 ? ? H11a .72267 .06821 .60911 .06200 Uiso ? ? 1.00000 ? ? H14a .59235 .43144 .40295 .06500 Uiso ? ? 1.00000 ? ? H15a .47914 .24820 .35380 .07400 Uiso ? ? 1.00000 ? ? H16a .53361 .05805 .40478 .07400 Uiso ? ? 1.00000 ? ? H17a .70335 .04890 .50543 .06500 Uiso ? ? 1.00000 ? ? H18a .85554 .43262 .55526 .04900 Uiso ? ? 1.00000 ? ? H9b .74961 1.09821 .29714 .07000 Uiso ? ? 1.00000 ? ? H10b .80180 1.01552 .18958 .07900 Uiso ? ? 1.00000 ? ? H11b .63845 .81132 .17534 .06500 Uiso ? ? 1.00000 ? ? H14b .39118 .57151 .39091 .05400 Uiso ? ? 1.00000 ? ? H15b .21131 .48162 .30518 .05900 Uiso ? ? 1.00000 ? ? H16b .19707 .56242 .20240 .06700 Uiso ? ? 1.00000 ? ? H17b .35934 .74040 .18511 .05900 Uiso ? ? 1.00000 ? ? H18b .59859 .85394 .38066 .04500 Uiso ? ? 1.00000 ? ? 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 .0682(5) .0386(4) .0488(4) -.0018(3) -.0017(3) -.0061(3) N1 .0512(12) .0363(13) .0417(12) .0030(10) .0026(10) .0026(10) C2 .0411(13) .0357(13) .0441(15) .0000(11) .0087(12) .0011(12) N3 .0439(12) .0344(12) .0452(13) .0014(9) .0051(10) .0016(10) C4 .0399(13) .0388(14) .0421(14) .0033(11) .0091(11) .0004(13) N5 .0525(13) .0346(12) .0430(13) .0035(10) .0059(11) .0004(10) C6 .0444(14) .0360(14) .0410(15) .0017(11) .0088(12) -.0018(12) N7a .0422(12) .0336(11) .0587(14) .0030(10) .0085(10) -.0002(11) N8a .0458(13) .0444(13) .0642(16) -.0018(11) .0051(12) .0022(12) C9a .0510(16) .0552(18) .061(2) .0099(14) .0023(14) .0006(16) C10a .0617(19) .0485(17) .075(2) .0106(15) .0055(17) .0133(16) C11a .0566(17) .0358(15) .075(2) .0064(13) .0083(16) .0095(14) C12a .0429(14) .0354(14) .0584(17) .0031(12) .0127(13) .0002(13) C13a .0446(14) .0391(14) .0527(17) .0004(12) .0083(13) -.0040(13) C14a .0676(19) .0494(17) .0558(18) -.0017(15) .0012(15) -.0049(15) C15a .073(2) .065(2) .063(2) -.0039(17) -.0013(16) -.0129(17) C16a .065(2) .0488(19) .080(2) -.0079(15) .0100(18) -.0150(17) C17a .0575(17) .0458(17) .070(2) -.0028(14) .0108(16) -.0064(15) N18a .0533(13) .0314(11) .0509(13) .0014(10) .0031(10) .0021(10) N7b .0487(12) .0414(12) .0459(13) .0051(10) .0058(10) .0029(10) N8b .0645(15) .0382(13) .0538(14) .0002(11) .0027(11) .0018(11) C9b .068(2) .0427(17) .079(2) -.0022(15) .0062(17) .0153(16) C10b .073(2) .058(2) .086(2) .0040(17) .0269(18) .0213(18) C11b .068(2) .0548(19) .0602(19) .0082(15) .0246(16) .0098(15) C12b .0428(14) .0383(14) .0457(16) .0073(11) .0073(12) -.0027(12) C13b .0374(13) .0358(14) .0477(15) .0073(11) .0076(11) -.0013(12) C14b .0401(14) .0460(15) .0620(18) .0018(12) .0110(13) .0012(14) C15b .0451(15) .0490(17) .076(2) -.0022(13) .0062(15) -.0072(16) C16b .0567(18) .059(2) .065(2) -.0029(15) -.0002(15) -.0163(16) C17b .0543(16) .0576(18) .0519(17) .0055(14) .0043(14) -.0100(14) N18b .0489(12) .0355(11) .0448(13) .0011(10) -.0002(10) .0022(10) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N18a H18a . . 1.024(2) ? N18a N8a . . 2.710(3) ? H18a N8a . . 1.874(2) ? N18b H18b . . 1.023(2) ? N18b N8b . . 2.729(3) ? H18b N8b . . 1.972(2) ? C17b H17b . . 1.066(3) ? C14a H14a . . 1.062(3) ? C14a N3 . . 2.891(4) ? H14a N3 . . 2.194(2) ? C14b H14b . . 1.062(3) ? C14b N3 . . 2.948(3) ? H14b N3 . . 2.428(2) ? CL1 C6 . . 1.743(2) ? N1 C6 . . 1.317(3) ? N1 C2 . . 1.356(3) ? C2 N3 . . 1.328(3) ? C2 N18a . . 1.368(3) ? N3 C4 . . 1.340(3) ? C4 N5 . . 1.350(3) ? C4 N18b . . 1.351(3) ? N5 C6 . . 1.306(3) ? N7a C11a . . 1.355(4) ? N7a N8a . . 1.369(3) ? N7a C12a . . 1.419(3) ? N8a C9a . . 1.314(4) ? C9a H9a . . 1.065(3) ? C9a C10a . . 1.396(4) ? C10a H10a . . 1.059(3) ? C10a C11a . . 1.371(4) ? C11a H11a . . 1.068(3) ? C12a C17a . . 1.397(4) ? C12a C13a . . 1.415(4) ? C13a C14a . . 1.393(4) ? C13a N18a . . 1.399(3) ? C14a H14a . . 1.062(3) ? C14a C15a . . 1.398(5) ? C15a H15a . . 1.065(3) ? C15a C16a . . 1.379(5) ? C16a H16a . . 1.054(3) ? C16a C17a . . 1.371(5) ? C17a H17a . . 1.056(3) ? N18a H18a . . 1.024(2) ? N7b C11b . . 1.356(4) ? N7b N8b . . 1.366(3) ? N7b C12b . . 1.431(3) ? N8b C9b . . 1.336(4) ? C9b H9b . . 1.054(3) ? C9b C10b . . 1.386(5) ? C10b H10b . . 1.065(4) ? C10b C11b . . 1.363(5) ? C11b H11b . . 1.057(3) ? C12b C17b . . 1.386(4) ? C12b C13b . . 1.395(4) ? C13b C14b . . 1.401(4) ? C13b N18b . . 1.404(3) ? C14b H14b . . 1.062(3) ? C14b C15b . . 1.387(4) ? C15b H15b . . 1.058(3) ? C15b C16b . . 1.374(5) ? C16b H16b . . 1.058(3) ? C16b C17b . . 1.391(4) ? C17b H17b . . 1.066(3) ? N18b H18b . . 1.023(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N18a H18a N8a . . . 136.39(13) ? N18b H18b N8b . . . 128.46(13) ? C14a H14a N3 . . . 121.19(17) ? C14b H14b N3 . . . 108.87(15) ? C6 N1 C2 . . . 111.7(2) ? N3 C2 N1 . . . 126.0(2) ? N3 C2 N18a . . . 120.9(2) ? N1 C2 N18a . . . 113.1(2) ? C2 N3 C4 . . . 114.2(2) ? N3 C4 N5 . . . 125.5(2) ? N3 C4 N18b . . . 120.3(2) ? N5 C4 N18b . . . 114.2(2) ? C6 N5 C4 . . . 112.4(2) ? N5 C6 N1 . . . 130.0(2) ? N5 C6 CL1 . . . 114.50(18) ? N1 C6 CL1 . . . 115.46(18) ? C11a N7a N8a . . . 110.6(2) ? C11a N7a C12a . . . 126.9(2) ? N8a N7a C12a . . . 122.5(2) ? C9a N8a N7a . . . 105.0(2) ? H9a C9a N8a . . . 124.3(3) ? H9a C9a C10a . . . 123.5(3) ? N8a C9a C10a . . . 112.3(3) ? H10a C10a C11a . . . 127.1(3) ? H10a C10a C9a . . . 128.3(3) ? C11a C10a C9a . . . 104.5(3) ? H11a C11a N7a . . . 126.3(3) ? H11a C11a C10a . . . 126.1(3) ? N7a C11a C10a . . . 107.5(2) ? C17a C12a C13a . . . 120.0(2) ? C17a C12a N7a . . . 117.4(2) ? C13a C12a N7a . . . 122.6(2) ? C14a C13a N18a . . . 123.4(2) ? C14a C13a C12a . . . 118.0(2) ? N18a C13a C12a . . . 118.6(2) ? H14a C14a C13a . . . 119.8(3) ? H14a C14a C15a . . . 119.4(3) ? C13a C14a C15a . . . 120.7(3) ? H15a C15a C16a . . . 119.9(3) ? H15a C15a C14a . . . 119.4(3) ? C16a C15a C14a . . . 120.7(3) ? H16a C16a C17a . . . 121.1(3) ? H16a C16a C15a . . . 119.5(3) ? C17a C16a C15a . . . 119.4(3) ? H17a C17a C16a . . . 119.5(3) ? H17a C17a C12a . . . 119.4(3) ? C16a C17a C12a . . . 121.1(3) ? H18a N18a C2 . . . 114.2(2) ? H18a N18a C13a . . . 114.6(2) ? C2 N18a C13a . . . 131.2(2) ? C11b N7b N8b . . . 111.5(2) ? C11b N7b C12b . . . 127.6(2) ? N8b N7b C12b . . . 121.0(2) ? C9b N8b N7b . . . 104.2(2) ? H9b C9b N8b . . . 122.5(3) ? H9b C9b C10b . . . 125.7(3) ? N8b C9b C10b . . . 111.8(3) ? H10b C10b C11b . . . 127.3(3) ? H10b C10b C9b . . . 127.1(3) ? C11b C10b C9b . . . 105.6(3) ? H11b C11b N7b . . . 126.1(3) ? H11b C11b C10b . . . 126.9(3) ? N7b C11b C10b . . . 107.0(3) ? C17b C12b C13b . . . 121.1(2) ? C17b C12b N7b . . . 117.2(2) ? C13b C12b N7b . . . 121.7(2) ? C12b C13b C14b . . . 118.2(2) ? C12b C13b N18b . . . 119.9(2) ? C14b C13b N18b . . . 121.8(2) ? H14b C14b C15b . . . 119.7(3) ? H14b C14b C13b . . . 120.1(2) ? C15b C14b C13b . . . 120.2(3) ? H15b C15b C16b . . . 119.9(3) ? H15b C15b C14b . . . 119.2(3) ? C16b C15b C14b . . . 120.9(3) ? H16b C16b C15b . . . 120.2(3) ? H16b C16b C17b . . . 120.2(3) ? C15b C16b C17b . . . 119.6(3) ? H17b C17b C12b . . . 120.4(3) ? H17b C17b C16b . . . 119.8(3) ? C12b C17b C16b . . . 119.9(3) ? H18b N18b C4 . . . 115.6(2) ? H18b N18b C13b . . . 114.9(2) ? C4 N18b C13b . . . 129.5(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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 N3 . . . . .2(4) ? C6 N1 C2 N18a . . . . 179.5(2) ? C2 N1 C6 CL1 . . . . 179.9(2) ? C2 N1 C6 N5 . . . . -.7(4) ? N1 C2 N3 C4 . . . . 1.0(4) ? N18a C2 N3 C4 . . . . -178.3(2) ? N1 C2 N18a C13a . . . . -179.5(3) ? N1 C2 N18a H18a . . . . .8(3) ? N3 C2 N18a C13a . . . . -.2(4) ? N3 C2 N18a H18a . . . . -179.9(2) ? C2 N3 C4 N5 . . . . -1.9(4) ? C2 N3 C4 N18b . . . . 176.2(2) ? N3 C4 N5 C6 . . . . 1.5(4) ? N18b C4 N5 C6 . . . . -176.7(2) ? N3 C4 N18b C13b . . . . 4.2(4) ? N3 C4 N18b H18b . . . . -175.0(2) ? N5 C4 N18b C13b . . . . -177.5(2) ? N5 C4 N18b H18b . . . . 3.3(3) ? C4 N5 C6 CL1 . . . . 179.3(2) ? C4 N5 C6 N1 . . . . -.1(4) ? C11a N7a N8a C9a . . . . .0(3) ? C12a N7a N8a C9a . . . . -178.5(2) ? N8a N7a C11a C10a . . . . -.4(3) ? N8a N7a C11a H11a . . . . 177.6(3) ? C12a N7a C11a C10a . . . . 178.0(3) ? C12a N7a C11a H11a . . . . -4.0(5) ? N8a N7a C12a C13a . . . . -29.9(4) ? N8a N7a C12a C17a . . . . 150.0(3) ? C11a N7a C12a C13a . . . . 151.8(3) ? C11a N7a C12a C17a . . . . -28.3(4) ? N7a N8a C9a C10a . . . . .4(3) ? N7a N8a C9a H9a . . . . -179.7(3) ? N8a C9a C10a C11a . . . . -.6(4) ? N8a C9a C10a H10a . . . . -179.1(3) ? H9a C9a C10a C11a . . . . 179.5(3) ? H9a C9a C10a H10a . . . . 1.0(6) ? C9a C10a C11a N7a . . . . .6(4) ? C9a C10a C11a H11a . . . . -177.4(3) ? H10a C10a C11a N7a . . . . 179.1(3) ? H10a C10a C11a H11a . . . . 1.1(6) ? N7a C12a C13a C14a . . . . -178.0(3) ? N7a C12a C13a N18a . . . . 1.0(4) ? C17a C12a C13a C14a . . . . 2.1(4) ? C17a C12a C13a N18a . . . . -178.9(3) ? N7a C12a C17a C16a . . . . 177.3(3) ? N7a C12a C17a H17a . . . . -1.7(4) ? C13a C12a C17a C16a . . . . -2.9(5) ? C13a C12a C17a H17a . . . . 178.1(3) ? C12a C13a C14a C15a . . . . -.4(5) ? C12a C13a C14a H14a . . . . 179.2(3) ? N18a C13a C14a C15a . . . . -179.4(3) ? N18a C13a C14a H14a . . . . .3(5) ? C12a C13a N18a C2 . . . . -174.5(3) ? C12a C13a N18a H18a . . . . 5.2(4) ? C14a C13a N18a C2 . . . . 4.5(5) ? C14a C13a N18a H18a . . . . -175.8(3) ? C13a C14a C15a C16a . . . . -.7(5) ? C13a C14a C15a H15a . . . . -179.7(3) ? H14a C14a C15a C16a . . . . 179.7(3) ? H14a C14a C15a H15a . . . . .6(5) ? C14a C15a C16a C17a . . . . .0(5) ? C14a C15a C16a H16a . . . . -179.2(3) ? H15a C15a C16a C17a . . . . 179.1(3) ? H15a C15a C16a H16a . . . . -.1(6) ? C15a C16a C17a C12a . . . . 1.7(5) ? C15a C16a C17a H17a . . . . -179.3(3) ? H16a C16a C17a C12a . . . . -179.0(3) ? H16a C16a C17a H17a . . . . -.0(6) ? C11b N7b N8b C9b . . . . -.7(3) ? C12b N7b N8b C9b . . . . 180.0(2) ? N8b N7b C11b C10b . . . . .6(3) ? N8b N7b C11b H11b . . . . -178.6(3) ? C12b N7b C11b C10b . . . . 179.8(3) ? C12b N7b C11b H11b . . . . .6(5) ? N8b N7b C12b C13b . . . . -37.9(3) ? N8b N7b C12b C17b . . . . 143.0(3) ? C11b N7b C12b C13b . . . . 143.0(3) ? C11b N7b C12b C17b . . . . -36.2(4) ? N7b N8b C9b C10b . . . . .6(3) ? N7b N8b C9b H9b . . . . -179.5(3) ? N8b C9b C10b C11b . . . . -.3(4) ? N8b C9b C10b H10b . . . . -179.4(3) ? H9b C9b C10b C11b . . . . 179.9(3) ? H9b C9b C10b H10b . . . . .8(6) ? C9b C10b C11b N7b . . . . -.2(3) ? C9b C10b C11b H11b . . . . 179.0(3) ? H10b C10b C11b N7b . . . . 178.9(3) ? H10b C10b C11b H11b . . . . -1.9(6) ? N7b C12b C13b C14b . . . . -177.7(2) ? N7b C12b C13b N18b . . . . 5.5(4) ? C17b C12b C13b C14b . . . . 1.4(4) ? C17b C12b C13b N18b . . . . -175.4(2) ? N7b C12b C17b C16b . . . . 176.9(3) ? N7b C12b C17b H17b . . . . -2.6(4) ? C13b C12b C17b C16b . . . . -2.2(4) ? C13b C12b C17b H17b . . . . 178.2(3) ? C12b C13b C14b C15b . . . . .3(4) ? C12b C13b C14b H14b . . . . -178.8(2) ? N18b C13b C14b C15b . . . . 177.0(2) ? N18b C13b C14b H14b . . . . -2.0(4) ? C12b C13b N18b C4 . . . . -150.3(3) ? C12b C13b N18b H18b . . . . 28.9(3) ? C14b C13b N18b C4 . . . . 33.0(4) ? C14b C13b N18b H18b . . . . -147.8(2) ? C13b C14b C15b C16b . . . . -1.1(4) ? C13b C14b C15b H15b . . . . -179.6(3) ? H14b C14b C15b C16b . . . . 177.9(3) ? H14b C14b C15b H15b . . . . -.6(4) ? C14b C15b C16b C17b . . . . .3(5) ? C14b C15b C16b H16b . . . . 178.6(3) ? H15b C15b C16b C17b . . . . 178.8(3) ? H15b C15b C16b H16b . . . . -2.9(5) ? C15b C16b C17b C12b . . . . 1.3(5) ? C15b C16b C17b H17b . . . . -179.1(3) ? H16b C16b C17b C12b . . . . -176.9(3) ? H16b C16b C17b H17b . . . . 2.6(5) ? 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_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N18a H18a N8a . . . 1.02 1.87 2.710(3) 136 ? N18b H18b N8b . . . 1.02 1.97 2.729(3) 128 ? C14a H14a N3 . . . 1.06 2.19 2.891(4) 121 ? C14b H14b N3 . . . 1-06 2.43 2.948(3) 109 ? C17b H17b CL1 1_555 1_555 4_464 1.07 2.78 3.570(3) 131 ? #-------------------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 888 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _reflns_number_observed ? _reflns_d_resolution_high .838 _reflns_d_resolution_low 10.93 _diffrn_reflns_av_sigmaI/netI .014 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_reduction_process 'equatorial monochr Lp' _diffrn_ambient_temperature 293 _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_radiation_detector ? _refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970' _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .054 _refine_ls_wR_factor_all .062 _refine_ls_goodness_of_fit_all .984 _refine_ls_shift/su_mean . #==========================================================================