# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_an655_TMZ_HCOOH_H2O _database_code_depnum_ccdc_archive 'CCDC 895908' #TrackingRef '15298_web_deposit_cif_file_1_AshwiniNangia_1352369055.an655_tmz_formicacid_water_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Hydrate of 1:1 cocrystal of Temozolomide and Formic acid' ; _chemical_name_common "'Hydrate of 1:1 cocrystal of Temozolomide and Formic acid'" _chemical_melting_point ? _chemical_formula_moiety '2(C6 H6 N6 O2), C H4 O3' _chemical_formula_sum 'C13 H16 N12 O7' _chemical_formula_weight 452.38 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' N N 0.0061 0.0033 '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' O O 0.0106 0.0060 '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 8.173(12) _cell_length_b 11.626(17) _cell_length_c 11.735(17) _cell_angle_alpha 64.73(2) _cell_angle_beta 74.09(3) _cell_angle_gamma 89.31(3) _cell_volume 963(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1938 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 23.06 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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 8751 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3278 _reflns_number_gt 1769 _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^)+(0.0676P)^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 3278 _refine_ls_number_parameters 318 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1475 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 O1 O -0.0809(4) -0.0299(2) 0.3825(2) 0.0764(9) Uani 1 1 d . . . O2 O 0.0477(3) 0.3909(2) -0.2582(2) 0.0662(8) Uani 1 1 d . . . N1 N 0.0642(4) 0.1494(3) 0.3488(3) 0.0569(9) Uani 1 1 d D . . N2 N -0.0937(4) 0.0775(3) 0.1206(3) 0.0511(8) Uani 1 1 d . . . N3 N 0.0130(3) 0.2710(2) -0.0367(2) 0.0427(7) Uani 1 1 d . . . N4 N 0.1648(3) 0.4702(2) -0.1463(2) 0.0469(8) Uani 1 1 d . . . N5 N 0.1920(4) 0.4632(3) -0.0331(3) 0.0510(8) Uani 1 1 d . . . N6 N 0.1351(3) 0.3626(2) 0.0748(3) 0.0454(7) Uani 1 1 d . . . C3 C 0.0474(4) 0.2622(3) 0.0756(3) 0.0403(8) Uani 1 1 d . . . C2 C -0.0203(4) 0.1417(3) 0.1726(3) 0.0428(9) Uani 1 1 d . . . C4 C -0.0729(4) 0.1559(3) -0.0025(3) 0.0505(9) Uani 1 1 d . . . H4 H -0.1119 0.1358 -0.0600 0.061 Uiso 1 1 calc R . . C5 C 0.0728(4) 0.3783(3) -0.1574(4) 0.0475(9) Uani 1 1 d . . . C6 C 0.2467(5) 0.5873(3) -0.2664(3) 0.0684(12) Uani 1 1 d . . . H6A H 0.3295 0.5653 -0.3275 0.103 Uiso 1 1 calc R . . H6B H 0.3030 0.6433 -0.2443 0.103 Uiso 1 1 calc R . . H6C H 0.1613 0.6296 -0.3062 0.103 Uiso 1 1 calc R . . C1 C -0.0152(4) 0.0811(3) 0.3104(3) 0.0484(9) Uani 1 1 d . . . O3 O 0.4404(3) 0.2825(2) -0.1227(2) 0.0646(8) Uani 1 1 d . . . O4 O 0.3679(3) -0.1441(2) 0.4770(2) 0.0642(8) Uani 1 1 d . . . N7 N 0.6124(4) 0.4057(3) -0.0873(4) 0.0621(10) Uani 1 1 d . . . N8 N 0.5528(4) 0.2250(3) 0.1724(3) 0.0571(8) Uani 1 1 d . . . N9 N 0.4247(4) 0.0273(3) 0.2737(3) 0.0464(7) Uani 1 1 d . . . N10 N 0.2849(4) -0.1604(3) 0.3124(3) 0.0528(8) Uani 1 1 d . . . N11 N 0.2698(4) -0.1085(3) 0.1864(3) 0.0556(8) Uani 1 1 d . . . N12 N 0.3286(4) 0.0069(3) 0.1060(3) 0.0511(8) Uani 1 1 d . . . C9 C 0.4113(4) 0.0784(3) 0.1468(3) 0.0422(8) Uani 1 1 d . . . C11 C 0.3611(5) -0.0984(3) 0.3655(4) 0.0508(9) Uani 1 1 d . . . C12 C 0.2191(5) -0.2970(3) 0.3911(4) 0.0770(13) Uani 1 1 d . . . H12A H 0.3122 -0.3457 0.4093 0.115 Uiso 1 1 calc R . . H12B H 0.1652 -0.3251 0.3428 0.115 Uiso 1 1 calc R . . H12C H 0.1369 -0.3093 0.4727 0.115 Uiso 1 1 calc R . . C10 C 0.5118(5) 0.1210(3) 0.2831(4) 0.0572(10) Uani 1 1 d . . . H14 H 0.5382 0.1117 0.3585 0.069 Uiso 1 1 calc R . . C8 C 0.4899(4) 0.2018(3) 0.0855(3) 0.0443(9) Uani 1 1 d . . . C7 C 0.5116(5) 0.2989(3) -0.0500(4) 0.0506(9) Uani 1 1 d . . . O6 O 0.2659(5) 0.3763(3) 0.3547(3) 0.1157(13) Uani 1 1 d . . . O7 O 0.3505(5) 0.3585(3) 0.5200(4) 0.1142(12) Uani 1 1 d . . . C13 C 0.2704(7) 0.3177(5) 0.4675(5) 0.0959(17) Uani 1 1 d . . . H13 H 0.2091 0.2364 0.5176 0.115 Uiso 1 1 calc R . . O5 O 0.3106(4) 0.1667(3) 0.7574(3) 0.0755(9) Uani 1 1 d . . . H1B H 0.118(3) 0.221(2) 0.301(3) 0.038(10) Uiso 1 1 d D . . H1A H 0.072(4) 0.112(3) 0.438(2) 0.070(12) Uiso 1 1 d D . . H5A H 0.232(6) 0.093(5) 0.797(5) 0.114(18) Uiso 1 1 d . . . H5B H 0.334(6) 0.175(5) 0.826(5) 0.14(2) Uiso 1 1 d . . . H7A H 0.641(4) 0.467(3) -0.163(3) 0.046(11) Uiso 1 1 d . . . H7B H 0.656(6) 0.407(4) -0.016(5) 0.14(2) Uiso 1 1 d . . . H7 H 0.330(8) 0.251(7) 0.641(8) 0.204 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 O1 0.124(2) 0.0470(16) 0.0484(16) -0.0060(13) -0.0340(15) -0.0190(16) O2 0.090(2) 0.0692(18) 0.0429(15) -0.0189(13) -0.0342(14) -0.0035(14) N1 0.074(2) 0.052(2) 0.0392(19) -0.0093(17) -0.0246(17) -0.0130(18) N2 0.056(2) 0.0506(18) 0.0449(18) -0.0183(16) -0.0173(15) -0.0056(15) N3 0.0507(18) 0.0411(16) 0.0341(16) -0.0118(13) -0.0166(13) -0.0047(13) N4 0.059(2) 0.0430(17) 0.0357(16) -0.0129(14) -0.0165(14) -0.0025(14) N5 0.062(2) 0.0465(18) 0.0437(18) -0.0168(15) -0.0188(15) -0.0037(15) N6 0.0569(19) 0.0371(16) 0.0401(17) -0.0141(14) -0.0159(14) -0.0032(14) C3 0.042(2) 0.048(2) 0.0336(18) -0.0186(16) -0.0139(16) 0.0014(17) C2 0.044(2) 0.049(2) 0.039(2) -0.0207(18) -0.0168(16) 0.0011(17) C4 0.060(2) 0.050(2) 0.044(2) -0.0203(19) -0.0186(18) -0.0051(19) C5 0.048(2) 0.048(2) 0.045(2) -0.0162(18) -0.0181(18) 0.0049(17) C6 0.086(3) 0.056(2) 0.046(2) -0.0079(19) -0.016(2) -0.017(2) C1 0.056(2) 0.043(2) 0.043(2) -0.0137(18) -0.0177(18) -0.0033(18) O3 0.092(2) 0.0554(16) 0.0593(17) -0.0270(14) -0.0393(15) 0.0056(14) O4 0.088(2) 0.0635(17) 0.0407(15) -0.0189(13) -0.0240(14) -0.0088(14) N7 0.077(3) 0.049(2) 0.049(2) -0.0101(19) -0.0195(19) -0.0074(18) N8 0.072(2) 0.0489(19) 0.0546(19) -0.0204(17) -0.0282(17) -0.0007(16) N9 0.058(2) 0.0452(17) 0.0441(17) -0.0227(14) -0.0231(14) 0.0023(14) N10 0.063(2) 0.0527(19) 0.0495(19) -0.0232(16) -0.0247(16) -0.0018(15) N11 0.065(2) 0.061(2) 0.0498(19) -0.0251(17) -0.0285(16) -0.0008(17) N12 0.059(2) 0.0501(19) 0.0509(18) -0.0235(16) -0.0241(15) -0.0002(15) C9 0.046(2) 0.050(2) 0.040(2) -0.0234(17) -0.0193(16) 0.0078(17) C11 0.053(2) 0.059(2) 0.046(2) -0.027(2) -0.0155(19) 0.0009(19) C12 0.101(3) 0.057(3) 0.065(3) -0.015(2) -0.031(2) -0.024(2) C10 0.075(3) 0.053(2) 0.053(2) -0.027(2) -0.028(2) -0.001(2) C8 0.054(2) 0.045(2) 0.041(2) -0.0206(17) -0.0217(17) 0.0074(17) C7 0.056(2) 0.048(2) 0.053(2) -0.0255(19) -0.0203(19) 0.0077(19) O6 0.162(3) 0.088(2) 0.072(2) -0.003(2) -0.049(2) -0.019(2) O7 0.131(3) 0.092(3) 0.095(3) -0.023(2) -0.027(2) -0.021(2) C13 0.120(4) 0.075(3) 0.073(4) -0.010(3) -0.034(3) -0.043(3) O5 0.091(2) 0.066(2) 0.064(2) -0.0208(17) -0.0264(18) -0.0126(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.227(4) . ? O2 C5 1.203(4) . ? N1 C1 1.317(4) . ? N1 H1B 0.820(17) . ? N1 H1A 0.964(19) . ? N2 C4 1.301(4) . ? N2 C2 1.374(4) . ? N3 C4 1.362(4) . ? N3 C3 1.383(4) . ? N3 C5 1.388(4) . ? N4 N5 1.375(4) . ? N4 C5 1.384(4) . ? N4 C6 1.468(4) . ? N5 N6 1.270(4) . ? N6 C3 1.372(4) . ? C3 C2 1.371(4) . ? C2 C1 1.475(5) . ? C4 H4 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? O3 C7 1.232(4) . ? O4 C11 1.201(4) . ? N7 C7 1.332(5) . ? N7 H7A 0.84(3) . ? N7 H7B 1.00(5) . ? N8 C10 1.300(4) . ? N8 C8 1.379(4) . ? N9 C10 1.367(4) . ? N9 C9 1.384(4) . ? N9 C11 1.390(4) . ? N10 C11 1.380(4) . ? N10 N11 1.379(4) . ? N10 C12 1.469(5) . ? N11 N12 1.268(4) . ? N12 C9 1.381(4) . ? C9 C8 1.369(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 H14 0.9300 . ? C8 C7 1.467(5) . ? O6 C13 1.214(5) . ? O7 C13 1.229(5) . ? O7 H7 1.40(8) . ? C13 H13 0.9300 . ? O5 H5A 0.94(5) . ? O5 H5B 0.92(6) . ? O5 H7 1.27(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1B 125(2) . . ? C1 N1 H1A 120(2) . . ? H1B N1 H1A 115(3) . . ? C4 N2 C2 107.0(3) . . ? C4 N3 C3 106.3(3) . . ? C4 N3 C5 131.4(3) . . ? C3 N3 C5 122.1(3) . . ? N5 N4 C5 126.7(3) . . ? N5 N4 C6 115.0(3) . . ? C5 N4 C6 118.2(3) . . ? N6 N5 N4 119.9(3) . . ? N5 N6 C3 118.9(3) . . ? C2 C3 N6 132.3(3) . . ? C2 C3 N3 106.3(3) . . ? N6 C3 N3 121.4(3) . . ? C3 C2 N2 108.8(3) . . ? C3 C2 C1 128.8(3) . . ? N2 C2 C1 122.4(3) . . ? N2 C4 N3 111.6(3) . . ? N2 C4 H4 124.2 . . ? N3 C4 H4 124.2 . . ? O2 C5 N4 124.2(3) . . ? O2 C5 N3 125.0(3) . . ? N4 C5 N3 110.8(3) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O1 C1 N1 123.2(3) . . ? O1 C1 C2 119.3(3) . . ? N1 C1 C2 117.5(3) . . ? C7 N7 H7A 125(2) . . ? C7 N7 H7B 114(3) . . ? H7A N7 H7B 121(4) . . ? C10 N8 C8 107.2(3) . . ? C10 N9 C9 106.9(3) . . ? C10 N9 C11 130.6(3) . . ? C9 N9 C11 122.5(3) . . ? C11 N10 N11 126.3(3) . . ? C11 N10 C12 119.3(3) . . ? N11 N10 C12 114.3(3) . . ? N12 N11 N10 120.8(3) . . ? N11 N12 C9 118.4(3) . . ? C8 C9 N12 133.0(3) . . ? C8 C9 N9 105.9(3) . . ? N12 C9 N9 121.1(3) . . ? O4 C11 N10 125.3(3) . . ? O4 C11 N9 123.8(3) . . ? N10 C11 N9 110.9(3) . . ? N10 C12 H12A 109.5 . . ? N10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N8 C10 N9 111.0(3) . . ? N8 C10 H14 124.5 . . ? N9 C10 H14 124.5 . . ? C9 C8 N8 109.0(3) . . ? C9 C8 C7 128.6(3) . . ? N8 C8 C7 122.4(3) . . ? O3 C7 N7 122.9(4) . . ? O3 C7 C8 122.1(3) . . ? N7 C7 C8 114.9(4) . . ? C13 O7 H7 101(3) . . ? O6 C13 O7 124.4(5) . . ? O6 C13 H13 117.8 . . ? O7 C13 H13 117.8 . . ? H5A O5 H5B 106(4) . . ? H5A O5 H7 122(4) . . ? H5B O5 H7 129(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.275 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.045 data_an1399_m_TMZ_HCl_2H2O _database_code_depnum_ccdc_archive 'CCDC 895909' #TrackingRef '15297_web_deposit_cif_file_0_AshwiniNangia_1352369055.an1399_tmz_hcl_dihydrate_final.cif' # start Validation Reply Form _vrf_PLAT340_an1399_m ; PROBLEM: PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.0115 Ang RESPONSE: The quality of the crystals were poor and twinned. Only major twin domian reflections were used for unit cell determnination and crystal structure solution. ; _vrf_PLAT934_an1399_m ; PROBLEM: PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers . 1 RESPONSE: This alert is due to twinning of the crystal. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6H7N6O2,C6H6N6O2, 2(Cl),H3O,3(H2O' _chemical_formula_sum 'C12 H22 Cl2 N12 O8' _chemical_formula_weight 533.32 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.453(15) _cell_length_b 10.37(2) _cell_length_c 17.84(4) _cell_angle_alpha 97.80(4) _cell_angle_beta 90.44(4) _cell_angle_gamma 98.27(4) _cell_volume 1171(5) _cell_formula_units_Z 2 _cell_measurement_temperature 446(2) _cell_measurement_reflns_used 1367 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 20.32 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8984 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 100(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 10750 _diffrn_reflns_av_R_equivalents 0.1006 _diffrn_reflns_av_sigmaI/netI 0.1237 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4115 _reflns_number_gt 2606 _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^)+(0.1144P)^2^+3.5904P] 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 4115 _refine_ls_number_parameters 360 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1885 _refine_ls_R_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.3157 _refine_ls_wR_factor_gt 0.2859 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.180 _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 Cl1 Cl 0.3889(4) 0.0921(2) 0.65597(14) 0.0597(8) Uani 1 1 d . . . Cl2 Cl 0.2105(4) 0.6143(3) 0.66859(16) 0.0616(8) Uani 1 1 d D . . O4 O 0.0427(10) 0.6331(6) 0.1071(3) 0.0525(17) Uani 1 1 d . . . O3 O 0.3361(10) 1.0680(6) -0.1150(3) 0.0483(16) Uani 1 1 d . . . N9 N 0.1598(11) 0.7523(6) 0.0125(4) 0.0347(16) Uani 1 1 d . . . N10 N 0.1321(11) 0.8579(7) 0.1330(4) 0.0413(18) Uani 1 1 d . . . N8 N 0.2044(12) 0.7211(6) -0.1092(4) 0.0423(18) Uani 1 1 d . . . N11 N 0.1883(12) 0.9773(6) 0.1107(4) 0.0414(18) Uani 1 1 d . . . N12 N 0.2270(11) 0.9889(6) 0.0423(4) 0.0396(17) Uani 1 1 d . . . C9 C 0.2159(13) 0.8755(7) -0.0088(5) 0.0328(19) Uani 1 1 d . . . C11 C 0.1058(13) 0.7375(8) 0.0873(5) 0.038(2) Uani 1 1 d . . . C8 C 0.2438(12) 0.8528(7) -0.0856(4) 0.0295(18) Uani 1 1 d . . . N7 N 0.3031(14) 0.8992(8) -0.2091(4) 0.048(2) Uani 1 1 d D . . C7 C 0.3013(13) 0.9489(8) -0.1386(5) 0.0353(19) Uani 1 1 d . . . C12 C 0.0898(17) 0.8615(9) 0.2139(5) 0.052(2) Uani 1 1 d . . . H12A H 0.0087 0.9305 0.2296 0.077 Uiso 1 1 calc R . . H12B H 0.2199 0.8775 0.2424 0.077 Uiso 1 1 calc R . . H12C H 0.0131 0.7787 0.2226 0.077 Uiso 1 1 calc R . . C10 C 0.1545(14) 0.6646(8) -0.0494(5) 0.042(2) Uani 1 1 d . . . H4 H 0.1197 0.5742 -0.0501 0.051 Uiso 1 1 calc R . . O10 O 0.3309(18) 0.8121(9) 0.5586(5) 0.091(3) Uani 1 1 d D . . O9 O 0.6800(12) 0.7268(6) -0.0094(4) 0.0499(17) Uani 1 1 d D . . O1 O 0.5066(10) 0.4384(6) 0.9170(3) 0.0505(17) Uani 1 1 d . . . N2 N 0.6649(12) 0.6493(6) 0.8458(4) 0.0377(17) Uani 1 1 d D . . N3 N 0.7197(11) 0.6651(6) 0.7299(4) 0.0352(16) Uani 1 1 d . . . N6 N 0.6201(12) 0.4422(7) 0.6704(4) 0.0458(19) Uani 1 1 d . . . O2 O 0.8210(11) 0.8259(6) 0.6562(4) 0.0579(19) Uani 1 1 d . . . C2 C 0.6111(13) 0.5241(8) 0.8071(4) 0.0349(19) Uani 1 1 d . . . N4 N 0.7253(11) 0.6092(7) 0.6016(4) 0.0404(18) Uani 1 1 d . . . N1 N 0.4723(13) 0.2991(7) 0.8072(4) 0.0457(19) Uani 1 1 d D . . C3 C 0.6434(14) 0.5323(7) 0.7333(4) 0.035(2) Uani 1 1 d . . . N5 N 0.6603(13) 0.4792(7) 0.6065(4) 0.051(2) Uani 1 1 d . . . C4 C 0.7333(13) 0.7327(8) 0.7995(4) 0.035(2) Uani 1 1 d . . . H10 H 0.7820 0.8218 0.8125 0.043 Uiso 1 1 calc R . . C5 C 0.7648(15) 0.7139(9) 0.6601(5) 0.046(2) Uani 1 1 d . . . C1 C 0.5233(15) 0.4161(8) 0.8491(5) 0.042(2) Uani 1 1 d . . . C6 C 0.7667(18) 0.6381(11) 0.5254(5) 0.065(3) Uani 1 1 d . . . H6A H 0.6851 0.5723 0.4898 0.098 Uiso 1 1 calc R . . H6B H 0.9129 0.6383 0.5158 0.098 Uiso 1 1 calc R . . H6C H 0.7295 0.7229 0.5203 0.098 Uiso 1 1 calc R . . O8 O 0.2262(15) 0.8373(8) 0.4311(5) 0.085(3) Uani 1 1 d D . . O11 O 0.0771(12) 0.3023(8) 0.6425(5) 0.075(2) Uani 1 1 d D . . H7A H 0.352(12) 0.959(6) -0.237(4) 0.04(2) Uiso 1 1 d D . . H7B H 0.227(12) 0.828(5) -0.232(4) 0.05(3) Uiso 1 1 d D . . H2 H 0.673(12) 0.678(7) 0.8943(11) 0.03(2) Uiso 1 1 d D . . H1A H 0.479(13) 0.290(8) 0.7581(8) 0.037 Uiso 1 1 d D . . H1B H 0.399(11) 0.241(6) 0.831(4) 0.037 Uiso 1 1 d D . . H9A H 0.700(16) 0.801(4) 0.014(5) 0.06(3) Uiso 1 1 d D . . H9B H 0.633(19) 0.663(7) 0.011(6) 0.10(5) Uiso 1 1 d D . . H8A H 0.142(15) 0.784(9) 0.404(4) 0.125 Uiso 1 1 d D . . H10A H 0.329(18) 0.877(6) 0.591(4) 0.07(4) Uiso 1 1 d D . . H8C H 0.329(9) 0.850(13) 0.405(4) 0.12(6) Uiso 1 1 d D . . H11A H 0.172(7) 0.257(5) 0.638(9) 0.146 Uiso 1 1 d D . . H11B H 0.137(10) 0.3783(12) 0.651(9) 0.146 Uiso 1 1 d D . . H8B H 0.246(13) 0.822(9) 0.474(2) 0.06(4) Uiso 1 1 d D . . H10B H 0.31(6) 0.76(2) 0.587(14) 0.36(19) Uiso 1 1 d 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 Cl1 0.0742(19) 0.0459(14) 0.0542(15) 0.0005(11) 0.0140(13) -0.0019(12) Cl2 0.0548(17) 0.0563(16) 0.0766(18) 0.0035(13) 0.0023(13) 0.0227(13) O4 0.065(5) 0.039(4) 0.052(4) 0.010(3) 0.011(3) -0.002(3) O3 0.071(5) 0.034(4) 0.039(3) 0.003(3) 0.003(3) 0.004(3) N9 0.039(4) 0.020(3) 0.044(4) 0.003(3) 0.003(3) 0.001(3) N10 0.040(5) 0.033(4) 0.050(4) 0.005(3) 0.008(3) 0.003(3) N8 0.052(5) 0.027(4) 0.046(4) 0.001(3) 0.008(4) 0.005(3) N11 0.052(5) 0.029(4) 0.045(4) 0.004(3) 0.011(4) 0.010(3) N12 0.041(4) 0.026(4) 0.054(5) 0.010(3) 0.003(3) 0.009(3) C9 0.035(5) 0.020(4) 0.044(5) 0.007(4) -0.002(4) 0.004(3) C11 0.035(5) 0.031(5) 0.049(5) 0.008(4) -0.001(4) 0.003(4) C8 0.031(5) 0.020(4) 0.037(5) -0.003(3) 0.004(3) 0.006(3) N7 0.064(6) 0.040(5) 0.042(5) 0.013(4) 0.008(4) 0.006(4) C7 0.030(5) 0.032(5) 0.042(5) -0.004(4) 0.000(4) 0.004(4) C12 0.069(7) 0.043(5) 0.044(5) 0.004(4) 0.011(5) 0.013(5) C10 0.055(6) 0.024(4) 0.048(5) 0.007(4) 0.003(4) 0.001(4) O10 0.140(9) 0.065(6) 0.054(5) -0.018(5) 0.002(5) -0.007(6) O9 0.075(5) 0.028(4) 0.045(4) 0.003(3) 0.014(3) 0.004(3) O1 0.073(5) 0.045(4) 0.035(4) 0.012(3) 0.016(3) 0.009(3) N2 0.050(5) 0.027(4) 0.033(4) -0.004(3) 0.006(3) 0.004(3) N3 0.038(4) 0.028(4) 0.043(4) 0.012(3) 0.007(3) 0.007(3) N6 0.057(5) 0.041(4) 0.037(4) 0.001(4) 0.011(4) 0.003(4) O2 0.075(5) 0.038(4) 0.061(4) 0.017(3) 0.011(4) 0.000(3) C2 0.035(5) 0.035(5) 0.036(5) -0.006(4) -0.003(4) 0.016(4) N4 0.038(4) 0.046(4) 0.036(4) 0.003(4) 0.003(3) 0.003(3) N1 0.065(6) 0.034(4) 0.039(4) 0.009(4) 0.012(4) 0.005(4) C3 0.047(6) 0.020(4) 0.037(5) -0.004(4) 0.002(4) 0.009(4) N5 0.061(6) 0.036(4) 0.048(5) -0.008(4) -0.001(4) -0.004(4) C4 0.040(5) 0.023(4) 0.039(5) -0.007(4) 0.008(4) 0.001(4) C5 0.041(6) 0.045(6) 0.056(6) 0.011(5) 0.007(4) 0.018(5) C1 0.050(6) 0.032(5) 0.048(6) 0.012(4) 0.010(4) 0.011(4) C6 0.074(8) 0.073(7) 0.049(6) 0.014(5) 0.003(5) 0.004(6) O8 0.088(7) 0.092(7) 0.067(6) 0.007(5) 0.014(5) -0.005(5) O11 0.072(5) 0.063(5) 0.092(6) 0.016(5) -0.009(5) 0.009(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 O4 C11 1.201(10) . ? O3 C7 1.238(10) . ? N9 C10 1.329(11) . ? N9 C9 1.381(10) . ? N9 C11 1.406(11) . ? N10 N11 1.353(10) . ? N10 C11 1.383(11) . ? N10 C12 1.467(11) . ? N8 C10 1.306(10) . ? N8 C8 1.360(10) . ? N11 N12 1.267(10) . ? N12 C9 1.380(11) . ? C9 C8 1.377(11) . ? C8 C7 1.476(11) . ? N7 C7 1.294(11) . ? N7 H7A 0.870(10) . ? N7 H7B 0.870(10) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 H4 0.9300 . ? O10 H10A 0.820(11) . ? O10 H10B 0.821(11) . ? O9 H9A 0.819(11) . ? O9 H9B 0.819(11) . ? O1 C1 1.211(10) . ? N2 C4 1.311(10) . ? N2 C2 1.382(11) . ? N2 H2 0.874(11) . ? N3 C4 1.336(10) . ? N3 C3 1.404(10) . ? N3 C5 1.423(11) . ? N6 N5 1.269(10) . ? N6 C3 1.351(11) . ? O2 C5 1.177(10) . ? C2 C3 1.347(11) . ? C2 C1 1.480(12) . ? N4 N5 1.369(10) . ? N4 C5 1.394(12) . ? N4 C6 1.449(11) . ? N1 C1 1.332(12) . ? N1 H1A 0.871(11) . ? N1 H1B 0.873(11) . ? C4 H10 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? O8 H8A 0.821(10) . ? O8 H8C 0.822(10) . ? O8 H8B 0.820(10) . ? O11 H11A 0.822(11) . ? O11 H11B 0.821(11) . ? 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 C10 N9 C9 107.6(7) . . ? C10 N9 C11 131.2(7) . . ? C9 N9 C11 121.0(7) . . ? N11 N10 C11 126.7(7) . . ? N11 N10 C12 114.6(7) . . ? C11 N10 C12 118.7(7) . . ? C10 N8 C8 106.9(7) . . ? N12 N11 N10 121.3(7) . . ? N11 N12 C9 117.9(6) . . ? C8 C9 N9 105.0(7) . . ? C8 C9 N12 132.9(7) . . ? N9 C9 N12 122.0(7) . . ? O4 C11 N10 125.9(8) . . ? O4 C11 N9 123.2(8) . . ? N10 C11 N9 110.9(7) . . ? N8 C8 C9 109.0(7) . . ? N8 C8 C7 122.1(7) . . ? C9 C8 C7 128.9(7) . . ? C7 N7 H7A 111(6) . . ? C7 N7 H7B 127(6) . . ? H7A N7 H7B 117(8) . . ? O3 C7 N7 124.5(8) . . ? O3 C7 C8 120.2(7) . . ? N7 C7 C8 115.2(8) . . ? N10 C12 H12A 109.5 . . ? N10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N8 C10 N9 111.5(7) . . ? N8 C10 H4 124.3 . . ? N9 C10 H4 124.3 . . ? H10A O10 H10B 98(10) . . ? H9A O9 H9B 122(10) . . ? C4 N2 C2 110.8(7) . . ? C4 N2 H2 117(5) . . ? C2 N2 H2 132(5) . . ? C4 N3 C3 109.8(6) . . ? C4 N3 C5 128.0(7) . . ? C3 N3 C5 122.2(7) . . ? N5 N6 C3 119.3(7) . . ? C3 C2 N2 107.0(7) . . ? C3 C2 C1 133.7(8) . . ? N2 C2 C1 119.2(7) . . ? N5 N4 C5 128.4(7) . . ? N5 N4 C6 114.5(7) . . ? C5 N4 C6 117.1(8) . . ? C1 N1 H1A 122(5) . . ? C1 N1 H1B 114(5) . . ? H1A N1 H1B 122(8) . . ? C2 C3 N6 133.0(8) . . ? C2 C3 N3 105.5(7) . . ? N6 C3 N3 121.5(7) . . ? N6 N5 N4 120.0(7) . . ? N2 C4 N3 106.9(7) . . ? N2 C4 H10 126.6 . . ? N3 C4 H10 126.6 . . ? O2 C5 N4 128.6(9) . . ? O2 C5 N3 122.9(9) . . ? N4 C5 N3 108.5(7) . . ? O1 C1 N1 125.3(8) . . ? O1 C1 C2 119.4(8) . . ? N1 C1 C2 115.3(8) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H8A O8 H8C 104(3) . . ? H8A O8 H8B 118(3) . . ? H8C O8 H8B 117(3) . . ? H11A O11 H11B 104.8(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 C11 N10 N11 N12 -1.2(13) . . . . ? C12 N10 N11 N12 -179.2(8) . . . . ? N10 N11 N12 C9 -1.8(12) . . . . ? C10 N9 C9 C8 -0.5(9) . . . . ? C11 N9 C9 C8 -176.1(7) . . . . ? C10 N9 C9 N12 177.2(8) . . . . ? C11 N9 C9 N12 1.7(12) . . . . ? N11 N12 C9 C8 178.6(9) . . . . ? N11 N12 C9 N9 1.6(12) . . . . ? N11 N10 C11 O4 -174.8(9) . . . . ? C12 N10 C11 O4 3.1(13) . . . . ? N11 N10 C11 N9 4.1(12) . . . . ? C12 N10 C11 N9 -178.0(7) . . . . ? C10 N9 C11 O4 0.5(15) . . . . ? C9 N9 C11 O4 174.8(8) . . . . ? C10 N9 C11 N10 -178.5(8) . . . . ? C9 N9 C11 N10 -4.1(11) . . . . ? C10 N8 C8 C9 -0.1(10) . . . . ? C10 N8 C8 C7 -178.7(8) . . . . ? N9 C9 C8 N8 0.4(9) . . . . ? N12 C9 C8 N8 -177.0(9) . . . . ? N9 C9 C8 C7 178.9(8) . . . . ? N12 C9 C8 C7 1.5(15) . . . . ? N8 C8 C7 O3 -180.0(8) . . . . ? C9 C8 C7 O3 1.7(13) . . . . ? N8 C8 C7 N7 2.6(12) . . . . ? C9 C8 C7 N7 -175.7(9) . . . . ? C8 N8 C10 N9 -0.2(10) . . . . ? C9 N9 C10 N8 0.5(10) . . . . ? C11 N9 C10 N8 175.4(8) . . . . ? C4 N2 C2 C3 -1.6(10) . . . . ? C4 N2 C2 C1 -178.0(8) . . . . ? N2 C2 C3 N6 179.2(9) . . . . ? C1 C2 C3 N6 -5.2(18) . . . . ? N2 C2 C3 N3 0.6(9) . . . . ? C1 C2 C3 N3 176.3(9) . . . . ? N5 N6 C3 C2 178.9(9) . . . . ? N5 N6 C3 N3 -2.7(13) . . . . ? C4 N3 C3 C2 0.4(9) . . . . ? C5 N3 C3 C2 -177.4(7) . . . . ? C4 N3 C3 N6 -178.3(8) . . . . ? C5 N3 C3 N6 3.8(12) . . . . ? C3 N6 N5 N4 -0.4(13) . . . . ? C5 N4 N5 N6 3.0(14) . . . . ? C6 N4 N5 N6 179.8(9) . . . . ? C2 N2 C4 N3 1.8(10) . . . . ? C3 N3 C4 N2 -1.4(9) . . . . ? C5 N3 C4 N2 176.3(8) . . . . ? N5 N4 C5 O2 179.8(9) . . . . ? C6 N4 C5 O2 3.1(14) . . . . ? N5 N4 C5 N3 -1.8(12) . . . . ? C6 N4 C5 N3 -178.6(8) . . . . ? C4 N3 C5 O2 -0.5(14) . . . . ? C3 N3 C5 O2 177.0(9) . . . . ? C4 N3 C5 N4 -178.9(8) . . . . ? C3 N3 C5 N4 -1.5(11) . . . . ? C3 C2 C1 O1 -177.7(9) . . . . ? N2 C2 C1 O1 -2.5(13) . . . . ? C3 C2 C1 N1 3.7(15) . . . . ? N2 C2 C1 N1 178.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.541 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.127