Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2002 data_global _publ_contact_author # Name and address of author for correspondence ; Luneau, Dominique Département de Chimie Université de Montréal CP 6128 Succursale Centre-Ville Montréal, Québec H3C 3J7 ; _publ_contact_author_phone '514 343-2247' _publ_contact_author_fax '514 343-7586' _publ_contact_author_email 'Dominique.Luneau@umontreal.ca' _publ_requested_journal 'DALTON' _journal_coden_Cambridge 186 _publ_contact_letter ; Please consider this CIF file submission in DALTON for three regular structure corresponding to compounds referenced as 2,3 and 4 in the manuscript. ; _publ_section_title ; New Schiff Base Zinc(II) Complexes Exhibiting Second-Harmonic Generation ; loop_ _publ_author_name _publ_author_address 'Evans, Cara' ; Laboratoire de Chimie Inorganique et Biologique (UMR 5046) Département de Recherche Fondamentale sur la Matière Condensée CEA-Grenoble 38054 Grenoble cedex 9, France ; 'Luneau, Dominique' ; Laboratoire de Chimie Inorganique et Biologique (UMR 5046) Département de Recherche Fondamentale sur la Matière Condensée CEA-Grenoble 38054 Grenoble cedex 9, France ; _publ_section_abstract ; Four bis(salicylaldiminato)zinc(II) complexes have been synthesized from four Schiff bases obtained by the condensation of chiral (R)-(+)-1-phenylethylamine with salicylaldehyde (1), 5-nitrosalicylaldehyde (2), 3,5-dichlorosalicylaldehyde (3) and 5-methoxysalicylaldehyde (4). The complexes crystallize in the noncentrosymmetric space groups P212121 (1), P21 (2), and C2 (3, 4). The geometry around the zinc(II) metal center is pseudo-tetrahedral with two oxygen and two nitrogen atoms from the ligands and has the L absolute configuration. Powders of the four compounds exhibit second harmonic generation (SHG) of intensity between that of 3-methyl-4-nitropyridine-1-oxide (POM) and N-(4-nitrophenyl)-(S)-prolinol (NPP). ; _publ_section_comment ; ; _publ_section_experimental ; Data were collected at room temperature on a Bruker SMART CCD diffractometer (l==0.71073?) and were processed through the SAINT reduction software. The structure was solved and refined on F2 using the SHELXTL software. ; data_dl626_2 _database_code_CSD 165067 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 N4 O6 Zn' _chemical_formula_weight 603.92 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.4512(8) _cell_length_b 10.1073(5) _cell_length_c 18.0725(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.5410(10) _cell_angle_gamma 90.00 _cell_volume 2822.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.920 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7697 _exptl_absorpt_correction_T_max 0.7697 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18371 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 29.01 _reflns_number_total 10989 _reflns_number_gt 8448 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(6) _refine_ls_number_reflns 10989 _refine_ls_number_parameters 739 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 0.614 _refine_ls_restrained_S_all 0.614 _refine_ls_shift/su_max 7.132 _refine_ls_shift/su_mean 0.406 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 ZnA Zn 0.317825(17) 1.01044(3) 0.714344(14) 0.04227(8) Uani 1 1 d . . . O1A O 0.43469(12) 1.0735(2) 0.72573(10) 0.0586(5) Uani 1 1 d . . . O2A O 0.30728(13) 0.83643(19) 0.67023(10) 0.0513(4) Uani 1 1 d . . . O3A O 0.66470(18) 1.3255(4) 0.97122(17) 0.1026(10) Uani 1 1 d . . . O4A O 0.5767(2) 1.2163(5) 1.03890(17) 0.1404(18) Uani 1 1 d . . . O5A O 0.0309(3) 0.5570(5) 0.4735(2) 0.1428(17) Uani 1 1 d . . . O6A O 0.0097(3) 0.7555(6) 0.4398(2) 0.1435(17) Uani 1 1 d . . . N1A N 0.29394(12) 0.9982(2) 0.82367(10) 0.0399(4) Uani 1 1 d . . . N2A N 0.25647(16) 1.1025(2) 0.63042(12) 0.0484(5) Uani 1 1 d . . . N3A N 0.60189(19) 1.2533(4) 0.97892(18) 0.0832(10) Uani 1 1 d . . . N4A N 0.0486(2) 0.6727(5) 0.4763(2) 0.0950(12) Uani 1 1 d . . . C1A C 0.47079(16) 1.1135(3) 0.78656(14) 0.0487(6) Uani 1 1 d . . . C2A C 0.55120(19) 1.1819(4) 0.78280(18) 0.0679(9) Uani 1 1 d . . . H2AA H 0.5762 1.1952 0.7368 0.082 Uiso 1 1 calc R . . C3A C 0.59256(19) 1.2283(4) 0.84388(19) 0.0699(9) Uani 1 1 d . . . H3AA H 0.6443 1.2744 0.8395 0.084 Uiso 1 1 calc R . . C4A C 0.55687(18) 1.2062(4) 0.91342(17) 0.0613(8) Uani 1 1 d . . . C5A C 0.47937(17) 1.1402(3) 0.92037(15) 0.0566(7) Uani 1 1 d . . . H5AA H 0.4570 1.1251 0.9672 0.068 Uiso 1 1 calc R . . C6A C 0.43401(16) 1.0955(3) 0.85796(14) 0.0457(6) Uani 1 1 d . . . C7A C 0.35099(15) 1.0342(3) 0.87155(13) 0.0442(6) Uani 1 1 d . . . H7AA H 0.3374 1.0191 0.9209 0.053 Uiso 1 1 calc R . . C8A C 0.21352(17) 0.9366(3) 0.85378(14) 0.0469(6) Uani 1 1 d . . . H8AA H 0.2110 0.9561 0.9068 0.056 Uiso 1 1 calc R . . C9A C 0.2200(2) 0.7881(3) 0.84440(19) 0.0660(9) Uani 1 1 d . . . H9AA H 0.2707 0.7563 0.8698 0.099 Uiso 1 1 calc R . . H9AB H 0.2238 0.7671 0.7927 0.099 Uiso 1 1 calc R . . H9AC H 0.1696 0.7468 0.8647 0.099 Uiso 1 1 calc R . . C10A C 0.13567(14) 0.9999(3) 0.81641(13) 0.0449(6) Uani 1 1 d . . . C11A C 0.10468(18) 0.9573(4) 0.74849(16) 0.0562(7) Uani 1 1 d . . . H11A H 0.1305 0.8852 0.7256 0.067 Uiso 1 1 calc R . . C12A C 0.03583(18) 1.0203(5) 0.71403(17) 0.0679(9) Uani 1 1 d . . . H12A H 0.0173 0.9925 0.6675 0.081 Uiso 1 1 calc R . . C13A C -0.0051(2) 1.1233(4) 0.7481(2) 0.0711(10) Uani 1 1 d . . . H13A H -0.0520 1.1646 0.7252 0.085 Uiso 1 1 calc R . . C14A C 0.0233(2) 1.1655(4) 0.8165(2) 0.0699(9) Uani 1 1 d . . . H14A H -0.0051 1.2341 0.8406 0.084 Uiso 1 1 calc R . . C15A C 0.09414(19) 1.1056(3) 0.84926(18) 0.0580(7) Uani 1 1 d . . . H15A H 0.1145 1.1370 0.8946 0.070 Uiso 1 1 calc R . . C16A C 0.24620(17) 0.8023(3) 0.62382(13) 0.0434(6) Uani 1 1 d . . . C17A C 0.2252(2) 0.6675(3) 0.61686(17) 0.0594(7) Uani 1 1 d . . . H17A H 0.2555 0.6052 0.6447 0.071 Uiso 1 1 calc R . . C18A C 0.1607(2) 0.6267(4) 0.56968(18) 0.0691(9) Uani 1 1 d . . . H18A H 0.1461 0.5375 0.5671 0.083 Uiso 1 1 calc R . . C19A C 0.1177(2) 0.7162(4) 0.52644(17) 0.0640(9) Uani 1 1 d . . . C20A C 0.13572(19) 0.8495(3) 0.53098(15) 0.0577(7) Uani 1 1 d . . . H20A H 0.1054 0.9091 0.5013 0.069 Uiso 1 1 calc R . . C21A C 0.19979(17) 0.8958(3) 0.58035(13) 0.0467(6) Uani 1 1 d . . . C22A C 0.2115(2) 1.0369(3) 0.58371(15) 0.0528(7) Uani 1 1 d . . . H22A H 0.1829 1.0861 0.5475 0.063 Uiso 1 1 calc R . . C23A C 0.2611(3) 1.2499(3) 0.61877(18) 0.0676(9) Uani 1 1 d . . . H23A H 0.2137 1.2759 0.5854 0.081 Uiso 1 1 calc R . . C24A C 0.3467(4) 1.2800(4) 0.5806(3) 0.117(2) Uani 1 1 d . . . H24A H 0.3493 1.2323 0.5347 0.175 Uiso 1 1 calc R . . H24B H 0.3940 1.2534 0.6121 0.175 Uiso 1 1 calc R . . H24C H 0.3506 1.3733 0.5710 0.175 Uiso 1 1 calc R . . C25A C 0.2499(2) 1.3207(3) 0.69085(18) 0.0611(8) Uani 1 1 d . . . C26A C 0.3184(3) 1.3543(4) 0.7373(2) 0.0851(11) Uani 1 1 d . . . H26A H 0.3747 1.3329 0.7239 0.102 Uiso 1 1 calc R . . C27A C 0.3034(5) 1.4198(5) 0.8037(3) 0.1097(17) Uani 1 1 d . . . H27A H 0.3494 1.4409 0.8351 0.132 Uiso 1 1 calc R . . C28A C 0.2206(6) 1.4528(5) 0.8225(3) 0.129(3) Uani 1 1 d . . . H28A H 0.2105 1.4970 0.8667 0.154 Uiso 1 1 calc R . . C29A C 0.1529(5) 1.4217(5) 0.7770(4) 0.127(2) Uani 1 1 d . . . H29A H 0.0968 1.4453 0.7897 0.152 Uiso 1 1 calc R . . C30A C 0.1682(3) 1.3556(4) 0.7126(3) 0.0879(12) Uani 1 1 d . . . H30A H 0.1214 1.3334 0.6823 0.105 Uiso 1 1 calc R . . ZnB Zn 0.74383(2) 0.88186(4) 0.737395(17) 0.05451(10) Uani 1 1 d . . . O1B O 0.76311(12) 1.0067(3) 0.81643(10) 0.0583(5) Uani 1 1 d . . . O2B O 0.72852(14) 0.9891(3) 0.65022(11) 0.0676(6) Uani 1 1 d . . . O3B O 1.0690(2) 0.9013(4) 1.03563(18) 0.1093(11) Uani 1 1 d . . . O4B O 1.0012(2) 1.0578(3) 1.09175(14) 0.0947(9) Uani 1 1 d . . . O5B O 0.4418(2) 1.0951(4) 0.41618(17) 0.1146(12) Uani 1 1 d . . . O6B O 0.37187(17) 0.9642(4) 0.48856(16) 0.0964(10) Uani 1 1 d . . . N1B N 0.85616(15) 0.7856(2) 0.74871(12) 0.0474(5) Uani 1 1 d . . . N2B N 0.62996(16) 0.7887(3) 0.73218(11) 0.0518(6) Uani 1 1 d . . . N3B N 1.0090(2) 0.9795(3) 1.04024(15) 0.0720(8) Uani 1 1 d . . . N4B N 0.4371(2) 1.0270(3) 0.47184(16) 0.0722(8) Uani 1 1 d . . . C1B C 0.82218(16) 0.9949(3) 0.86715(13) 0.0450(6) Uani 1 1 d . . . C2B C 0.82113(19) 1.0862(3) 0.92709(16) 0.0546(7) Uani 1 1 d . . . H2BA H 0.7788 1.1517 0.9282 0.066 Uiso 1 1 calc R . . C3B C 0.8812(2) 1.0797(3) 0.98323(15) 0.0548(7) Uani 1 1 d . . . H3BA H 0.8794 1.1399 1.0221 0.066 Uiso 1 1 calc R . . C4B C 0.94454(18) 0.9830(3) 0.98176(14) 0.0498(7) Uani 1 1 d . . . C5B C 0.94983(17) 0.8949(3) 0.92443(13) 0.0460(6) Uani 1 1 d . . . H5BA H 0.9939 0.8322 0.9241 0.055 Uiso 1 1 calc R . . C6B C 0.88917(16) 0.8988(3) 0.86628(13) 0.0409(5) Uani 1 1 d . . . C7B C 0.90416(18) 0.8074(3) 0.80573(14) 0.0451(6) Uani 1 1 d . . . H7BA H 0.9550 0.7584 0.8087 0.054 Uiso 1 1 calc R . . C8B C 0.8880(2) 0.6896(3) 0.69300(16) 0.0579(7) Uani 1 1 d . . . H8BA H 0.9498 0.6749 0.7027 0.069 Uiso 1 1 calc R . . C9B C 0.8789(3) 0.7518(5) 0.61609(18) 0.0972(15) Uani 1 1 d . . . H9BA H 0.9097 0.8343 0.6150 0.146 Uiso 1 1 calc R . . H9BB H 0.8188 0.7673 0.6052 0.146 Uiso 1 1 calc R . . H9BC H 0.9024 0.6929 0.5798 0.146 Uiso 1 1 calc R . . C10B C 0.84212(17) 0.5583(3) 0.70139(14) 0.0468(6) Uani 1 1 d . . . C11B C 0.7796(2) 0.5136(4) 0.65245(16) 0.0646(8) Uani 1 1 d . . . H11B H 0.7630 0.5662 0.6125 0.078 Uiso 1 1 calc R . . C12B C 0.7411(3) 0.3909(4) 0.6622(2) 0.0798(10) Uani 1 1 d . . . H12B H 0.6990 0.3620 0.6288 0.096 Uiso 1 1 calc R . . C13B C 0.7645(2) 0.3124(4) 0.7204(2) 0.0706(9) Uani 1 1 d . . . H13B H 0.7400 0.2290 0.7256 0.085 Uiso 1 1 calc R . . C14B C 0.8237(2) 0.3563(4) 0.77050(19) 0.0675(8) Uani 1 1 d . . . H14B H 0.8385 0.3042 0.8111 0.081 Uiso 1 1 calc R . . C15B C 0.86217(19) 0.4787(3) 0.76119(17) 0.0575(8) Uani 1 1 d . . . H15B H 0.9025 0.5080 0.7960 0.069 Uiso 1 1 calc R . . C16B C 0.65766(17) 0.9974(3) 0.61182(13) 0.0501(6) Uani 1 1 d . . . C17B C 0.6550(2) 1.0870(3) 0.55183(15) 0.0580(7) Uani 1 1 d . . . H17B H 0.7028 1.1406 0.5433 0.070 Uiso 1 1 calc R . . C18B C 0.5845(2) 1.0975(3) 0.50601(16) 0.0593(7) Uani 1 1 d . . . H18B H 0.5847 1.1556 0.4661 0.071 Uiso 1 1 calc R . . C19B C 0.51175(19) 1.0192(4) 0.52030(15) 0.0558(7) Uani 1 1 d . . . C20B C 0.51017(18) 0.9345(3) 0.57893(15) 0.0518(7) Uani 1 1 d . . . H20B H 0.4604 0.8854 0.5880 0.062 Uiso 1 1 calc R . . C21B C 0.58194(17) 0.9201(3) 0.62556(13) 0.0460(6) Uani 1 1 d . . . C22B C 0.57245(18) 0.8232(3) 0.68429(14) 0.0491(6) Uani 1 1 d . . . H22B H 0.5189 0.7817 0.6875 0.059 Uiso 1 1 calc R . . C23B C 0.6112(2) 0.6785(4) 0.78471(16) 0.0683(9) Uani 1 1 d . . . H23B H 0.6432 0.6012 0.7670 0.082 Uiso 1 1 calc R . . C24B C 0.5179(3) 0.6369(6) 0.7905(2) 0.112(2) Uani 1 1 d . . . H24D H 0.4959 0.6148 0.7422 0.168 Uiso 1 1 calc R . . H24E H 0.4846 0.7083 0.8106 0.168 Uiso 1 1 calc R . . H24F H 0.5138 0.5611 0.8223 0.168 Uiso 1 1 calc R . . C25B C 0.6494(2) 0.7135(3) 0.85940(15) 0.0536(7) Uani 1 1 d . . . C26B C 0.6198(2) 0.8205(4) 0.89891(17) 0.0655(8) Uani 1 1 d . . . H26B H 0.5753 0.8728 0.8800 0.079 Uiso 1 1 calc R . . C27B C 0.6574(3) 0.8504(4) 0.96820(19) 0.0827(12) Uani 1 1 d . . . H27B H 0.6378 0.9228 0.9950 0.099 Uiso 1 1 calc R . . C28B C 0.7229(3) 0.7730(5) 0.9961(2) 0.0865(13) Uani 1 1 d . . . H28B H 0.7480 0.7931 1.0417 0.104 Uiso 1 1 calc R . . C29B C 0.7507(3) 0.6675(5) 0.9573(2) 0.0849(12) Uani 1 1 d . . . H29B H 0.7947 0.6146 0.9766 0.102 Uiso 1 1 calc R . . C30B C 0.7149(2) 0.6377(4) 0.88999(18) 0.0695(9) Uani 1 1 d . . . H30B H 0.7351 0.5647 0.8641 0.083 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 ZnA 0.04546(15) 0.04516(15) 0.03610(13) -0.00071(13) -0.00439(10) -0.00580(14) O1A 0.0466(10) 0.0869(15) 0.0424(10) -0.0123(10) 0.0030(8) -0.0143(10) O2A 0.0664(11) 0.0407(10) 0.0464(10) -0.0048(8) -0.0154(8) 0.0020(9) O3A 0.0756(17) 0.124(3) 0.108(2) -0.0475(19) -0.0180(15) -0.0266(17) O4A 0.088(2) 0.272(6) 0.0609(17) -0.041(2) -0.0126(15) -0.055(3) O5A 0.149(3) 0.150(4) 0.129(3) -0.043(3) -0.021(2) -0.084(3) O6A 0.118(3) 0.183(5) 0.129(3) -0.054(3) -0.069(2) 0.004(3) N1A 0.0390(9) 0.0444(11) 0.0363(9) 0.0026(9) -0.0025(7) -0.0026(10) N2A 0.0639(14) 0.0407(12) 0.0405(11) 0.0059(9) 0.0000(10) -0.0005(10) N3A 0.0514(15) 0.121(3) 0.076(2) -0.042(2) -0.0140(14) -0.0032(17) N4A 0.082(2) 0.124(3) 0.079(2) -0.040(2) -0.0145(18) -0.031(2) C1A 0.0383(13) 0.0612(18) 0.0466(14) -0.0114(13) 0.0003(11) 0.0002(12) C2A 0.0478(15) 0.099(3) 0.0575(17) -0.0078(17) 0.0051(13) -0.0180(17) C3A 0.0442(15) 0.087(3) 0.079(2) -0.0162(19) -0.0030(15) -0.0152(16) C4A 0.0413(14) 0.083(2) 0.0588(17) -0.0231(16) -0.0090(13) 0.0022(15) C5A 0.0428(14) 0.078(2) 0.0494(15) -0.0152(15) -0.0039(11) 0.0056(14) C6A 0.0366(12) 0.0552(16) 0.0451(13) -0.0064(12) -0.0045(10) 0.0054(11) C7A 0.0418(12) 0.0550(18) 0.0358(11) -0.0026(11) -0.0005(10) 0.0044(11) C8A 0.0471(14) 0.0562(17) 0.0375(13) 0.0090(11) -0.0002(11) -0.0077(12) C9A 0.070(2) 0.056(2) 0.073(2) 0.0237(16) -0.0067(16) -0.0141(16) C10A 0.0371(11) 0.0537(15) 0.0439(12) 0.0071(13) 0.0029(9) -0.0119(13) C11A 0.0421(14) 0.078(2) 0.0486(15) -0.0029(14) 0.0050(12) -0.0013(13) C12A 0.0488(15) 0.103(3) 0.0512(15) 0.009(2) -0.0075(12) -0.009(2) C13A 0.0477(16) 0.086(3) 0.079(2) 0.022(2) -0.0022(16) 0.0008(18) C14A 0.0546(17) 0.062(2) 0.093(2) 0.0045(19) 0.0060(17) 0.0061(15) C15A 0.0536(16) 0.0558(18) 0.0646(18) 0.0000(14) -0.0006(14) -0.0111(14) C16A 0.0523(14) 0.0437(15) 0.0341(12) -0.0038(10) 0.0006(11) -0.0020(11) C17A 0.080(2) 0.0440(17) 0.0545(16) -0.0037(13) 0.0000(15) -0.0078(15) C18A 0.086(2) 0.0560(19) 0.0656(19) -0.0155(16) 0.0070(17) -0.0259(18) C19A 0.0579(17) 0.082(2) 0.0523(16) -0.0235(16) 0.0009(13) -0.0203(17) C20A 0.0568(16) 0.072(2) 0.0439(14) -0.0070(13) -0.0079(12) -0.0017(15) C21A 0.0524(14) 0.0498(16) 0.0378(12) -0.0017(12) -0.0029(10) -0.0034(13) C22A 0.0673(17) 0.0523(19) 0.0388(13) 0.0077(11) -0.0092(12) 0.0035(13) C23A 0.107(3) 0.0398(16) 0.0557(17) 0.0101(14) 0.0035(17) 0.0004(17) C24A 0.194(5) 0.053(2) 0.105(3) 0.001(2) 0.079(3) -0.031(3) C25A 0.086(2) 0.0344(14) 0.0630(18) 0.0072(13) 0.0062(16) -0.0063(15) C26A 0.114(3) 0.058(2) 0.084(2) -0.0052(19) -0.003(2) -0.003(2) C27A 0.174(5) 0.069(3) 0.086(3) -0.011(2) -0.015(3) -0.015(3) C28A 0.244(9) 0.051(2) 0.092(4) -0.001(2) 0.056(5) -0.006(4) C29A 0.163(6) 0.067(3) 0.152(5) -0.002(3) 0.091(5) -0.005(3) C30A 0.101(3) 0.053(2) 0.110(3) 0.011(2) 0.027(3) -0.009(2) ZnB 0.05813(19) 0.0601(2) 0.04497(16) -0.00014(15) -0.01563(13) -0.01134(16) O1B 0.0596(10) 0.0609(12) 0.0540(10) -0.0082(11) -0.0210(8) 0.0062(11) O2B 0.0623(11) 0.0864(18) 0.0538(11) 0.0192(11) -0.0198(9) -0.0280(12) O3B 0.118(2) 0.099(2) 0.110(2) -0.0163(18) -0.0735(19) 0.024(2) O4B 0.129(2) 0.094(2) 0.0600(14) -0.0200(13) -0.0428(15) -0.0106(17) O5B 0.120(2) 0.124(3) 0.099(2) 0.047(2) -0.0516(19) -0.011(2) O6B 0.0661(15) 0.134(3) 0.0891(18) 0.0145(18) -0.0270(13) -0.0096(16) N1B 0.0571(13) 0.0463(13) 0.0389(11) -0.0071(9) -0.0035(9) -0.0132(10) N2B 0.0643(15) 0.0561(15) 0.0349(11) 0.0018(10) -0.0046(10) -0.0149(12) N3B 0.095(2) 0.066(2) 0.0543(15) 0.0006(13) -0.0325(14) -0.0137(16) N4B 0.0750(18) 0.075(2) 0.0659(16) 0.0040(16) -0.0217(14) 0.0104(16) C1B 0.0495(13) 0.0462(15) 0.0392(11) -0.0023(12) -0.0040(10) -0.0076(13) C2B 0.0567(16) 0.0563(18) 0.0508(15) -0.0088(13) -0.0015(12) 0.0023(14) C3B 0.0698(18) 0.0556(17) 0.0390(13) -0.0104(12) -0.0025(12) -0.0126(15) C4B 0.0576(15) 0.0547(19) 0.0369(12) 0.0019(11) -0.0113(11) -0.0136(13) C5B 0.0504(13) 0.0447(15) 0.0428(12) 0.0049(11) -0.0074(10) -0.0053(12) C6B 0.0476(13) 0.0393(14) 0.0359(11) -0.0004(10) -0.0031(9) -0.0099(11) C7B 0.0474(14) 0.0417(14) 0.0461(14) -0.0004(11) 0.0003(11) -0.0069(11) C8B 0.0641(17) 0.0624(19) 0.0474(15) -0.0144(14) 0.0050(13) -0.0112(15) C9B 0.164(4) 0.081(3) 0.0470(18) -0.0081(18) 0.019(2) -0.035(3) C10B 0.0471(13) 0.0510(15) 0.0423(13) -0.0134(11) -0.0024(11) 0.0023(12) C11B 0.0755(18) 0.0650(19) 0.0530(15) -0.0035(16) -0.0225(14) -0.0064(19) C12B 0.081(2) 0.076(3) 0.082(2) -0.017(2) -0.0269(18) -0.015(2) C13B 0.071(2) 0.0469(18) 0.094(3) -0.0073(18) 0.0088(19) -0.0012(16) C14B 0.0662(19) 0.062(2) 0.074(2) 0.0115(17) -0.0021(16) 0.0142(16) C15B 0.0521(15) 0.064(2) 0.0557(16) -0.0032(14) -0.0152(12) 0.0050(14) C16B 0.0545(14) 0.0583(16) 0.0374(11) -0.0013(13) -0.0047(10) -0.0074(14) C17B 0.0709(19) 0.0577(19) 0.0455(15) 0.0033(13) -0.0008(13) -0.0109(15) C18B 0.0715(19) 0.0574(19) 0.0488(15) 0.0041(13) -0.0078(14) 0.0012(15) C19B 0.0595(15) 0.0603(18) 0.0474(14) -0.0048(15) -0.0082(12) 0.0125(16) C20B 0.0492(14) 0.0600(17) 0.0462(14) -0.0073(13) -0.0041(12) 0.0011(13) C21B 0.0503(14) 0.0549(17) 0.0328(11) -0.0051(10) -0.0014(10) -0.0056(12) C22B 0.0495(14) 0.0606(17) 0.0371(13) -0.0049(12) -0.0012(11) -0.0130(13) C23B 0.101(3) 0.0570(19) 0.0470(15) 0.0052(14) -0.0079(16) -0.0258(18) C24B 0.115(3) 0.151(5) 0.069(2) 0.039(3) -0.021(2) -0.078(4) C25B 0.0652(17) 0.0538(17) 0.0418(13) 0.0097(12) 0.0016(12) -0.0039(14) C26B 0.083(2) 0.0601(19) 0.0537(17) 0.0060(14) 0.0004(15) 0.0064(17) C27B 0.120(3) 0.076(3) 0.0519(18) -0.0071(17) 0.015(2) -0.014(2) C28B 0.102(3) 0.108(4) 0.0491(18) 0.018(2) -0.0112(19) -0.025(3) C29B 0.077(2) 0.109(4) 0.068(2) 0.033(2) -0.0084(18) 0.003(2) C30B 0.078(2) 0.072(2) 0.0581(18) 0.0181(17) 0.0113(16) 0.0081(18) _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 ZnA O2A 1.9373(19) . ? ZnA O1A 1.9242(19) . ? ZnA N1A 2.0172(19) . ? ZnA N2A 2.010(2) . ? O1A C1A 1.293(3) . ? O2A C16A 1.303(3) . ? O3A N3A 1.223(5) . ? O4A N3A 1.214(5) . ? O5A N4A 1.201(6) . ? O6A N4A 1.222(6) . ? N1A C7A 1.282(3) . ? N1A C8A 1.497(3) . ? N2A C22A 1.274(4) . ? N2A C23A 1.506(4) . ? N3A C4A 1.448(4) . ? N4A C19A 1.461(4) . ? C1A C2A 1.424(4) . ? C1A C6A 1.427(4) . ? C2A C3A 1.354(4) . ? C3A C4A 1.395(5) . ? C4A C5A 1.378(4) . ? C5A C6A 1.397(4) . ? C6A C7A 1.448(4) . ? C8A C10A 1.516(4) . ? C8A C9A 1.513(5) . ? C10A C15A 1.383(4) . ? C10A C11A 1.382(4) . ? C11A C12A 1.383(4) . ? C12A C13A 1.368(6) . ? C13A C14A 1.375(5) . ? C14A C15A 1.380(5) . ? C16A C17A 1.405(4) . ? C16A C21A 1.419(4) . ? C17A C18A 1.369(5) . ? C18A C19A 1.364(5) . ? C19A C20A 1.379(5) . ? C20A C21A 1.406(4) . ? C21A C22A 1.439(4) . ? C23A C25A 1.498(5) . ? C23A C24A 1.528(5) . ? C25A C30A 1.371(5) . ? C25A C26A 1.387(5) . ? C26A C27A 1.392(7) . ? C27A C28A 1.369(9) . ? C28A C29A 1.360(9) . ? C29A C30A 1.364(7) . ? ZnB O2B 1.925(2) . ? ZnB O1B 1.927(2) . ? ZnB N2B 1.997(2) . ? ZnB N1B 1.999(3) . ? O1B C1B 1.293(3) . ? O2B C16B 1.294(3) . ? O3B N3B 1.221(4) . ? O4B N3B 1.229(4) . ? O5B N4B 1.221(4) . ? O6B N4B 1.231(4) . ? N1B C7B 1.283(3) . ? N1B C8B 1.486(4) . ? N2B C22B 1.283(4) . ? N2B C23B 1.493(4) . ? N3B C4B 1.446(3) . ? N4B C19B 1.444(4) . ? C1B C2B 1.424(4) . ? C1B C6B 1.420(4) . ? C2B C3B 1.370(4) . ? C3B C4B 1.383(4) . ? C4B C5B 1.369(4) . ? C5B C6B 1.402(3) . ? C6B C7B 1.452(4) . ? C8B C10B 1.513(4) . ? C8B C9B 1.531(5) . ? C10B C15B 1.380(4) . ? C10B C11B 1.380(4) . ? C11B C12B 1.387(6) . ? C12B C13B 1.363(5) . ? C13B C14B 1.356(5) . ? C14B C15B 1.383(5) . ? C16B C17B 1.413(4) . ? C16B C21B 1.430(4) . ? C17B C18B 1.367(4) . ? C18B C19B 1.400(5) . ? C19B C20B 1.363(4) . ? C20B C21B 1.394(4) . ? C21B C22B 1.453(4) . ? C23B C25B 1.510(4) . ? C23B C24B 1.506(5) . ? C25B C26B 1.376(5) . ? C25B C30B 1.380(5) . ? C26B C27B 1.408(5) . ? C27B C28B 1.372(6) . ? C28B C29B 1.349(7) . ? C29B C30B 1.366(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 O2A ZnA O1A 114.84(9) . . ? O2A ZnA N1A 109.39(9) . . ? O1A ZnA N1A 95.49(8) . . ? O2A ZnA N2A 94.17(9) . . ? O1A ZnA N2A 111.27(10) . . ? N1A ZnA N2A 132.70(9) . . ? C1A O1A ZnA 126.26(17) . . ? C16A O2A ZnA 124.26(17) . . ? C7A N1A C8A 116.1(2) . . ? C7A N1A ZnA 120.85(16) . . ? C8A N1A ZnA 122.80(16) . . ? C22A N2A C23A 116.7(2) . . ? C22A N2A ZnA 120.60(19) . . ? C23A N2A ZnA 122.7(2) . . ? O4A N3A O3A 123.1(3) . . ? O4A N3A C4A 118.2(3) . . ? O3A N3A C4A 118.6(3) . . ? O6A N4A O5A 122.2(4) . . ? O6A N4A C19A 118.8(4) . . ? O5A N4A C19A 118.9(5) . . ? O1A C1A C2A 118.7(2) . . ? O1A C1A C6A 123.8(2) . . ? C2A C1A C6A 117.4(2) . . ? C3A C2A C1A 122.3(3) . . ? C2A C3A C4A 119.4(3) . . ? C5A C4A C3A 120.7(3) . . ? C5A C4A N3A 119.7(3) . . ? C3A C4A N3A 119.5(3) . . ? C4A C5A C6A 120.8(3) . . ? C5A C6A C1A 119.2(2) . . ? C5A C6A C7A 116.1(2) . . ? C1A C6A C7A 124.7(2) . . ? N1A C7A C6A 127.7(2) . . ? N1A C8A C10A 108.7(2) . . ? N1A C8A C9A 108.4(2) . . ? C10A C8A C9A 114.9(3) . . ? C15A C10A C11A 117.6(3) . . ? C15A C10A C8A 120.3(2) . . ? C11A C10A C8A 122.1(3) . . ? C12A C11A C10A 121.0(3) . . ? C13A C12A C11A 120.3(3) . . ? C12A C13A C14A 119.8(3) . . ? C13A C14A C15A 119.6(3) . . ? C10A C15A C14A 121.7(3) . . ? O2A C16A C17A 118.6(3) . . ? O2A C16A C21A 122.6(2) . . ? C17A C16A C21A 118.7(3) . . ? C18A C17A C16A 120.9(3) . . ? C19A C18A C17A 120.3(3) . . ? C18A C19A C20A 121.1(3) . . ? C18A C19A N4A 120.3(4) . . ? C20A C19A N4A 118.5(4) . . ? C19A C20A C21A 120.2(3) . . ? C20A C21A C16A 118.6(3) . . ? C20A C21A C22A 116.3(3) . . ? C16A C21A C22A 125.0(2) . . ? N2A C22A C21A 127.7(2) . . ? C25A C23A N2A 110.1(2) . . ? C25A C23A C24A 114.0(3) . . ? N2A C23A C24A 107.6(3) . . ? C30A C25A C26A 117.6(4) . . ? C30A C25A C23A 119.2(4) . . ? C26A C25A C23A 123.3(3) . . ? C25A C26A C27A 120.4(5) . . ? C28A C27A C26A 119.6(6) . . ? C27A C28A C29A 120.6(5) . . ? C28A C29A C30A 119.4(6) . . ? C25A C30A C29A 122.5(5) . . ? O2B ZnB O1B 104.76(11) . . ? O2B ZnB N2B 97.22(9) . . ? O1B ZnB N2B 118.28(9) . . ? O2B ZnB N1B 117.24(10) . . ? O1B ZnB N1B 96.60(8) . . ? N2B ZnB N1B 122.62(10) . . ? C1B O1B ZnB 124.6(2) . . ? C16B O2B ZnB 124.91(19) . . ? C7B N1B C8B 117.6(3) . . ? C7B N1B ZnB 119.6(2) . . ? C8B N1B ZnB 122.78(18) . . ? C22B N2B C23B 119.6(3) . . ? C22B N2B ZnB 120.5(2) . . ? C23B N2B ZnB 119.84(19) . . ? O3B N3B O4B 123.3(3) . . ? O3B N3B C4B 119.0(3) . . ? O4B N3B C4B 117.7(3) . . ? O5B N4B O6B 123.2(3) . . ? O5B N4B C19B 118.5(3) . . ? O6B N4B C19B 118.3(3) . . ? O1B C1B C2B 117.8(3) . . ? O1B C1B C6B 124.4(2) . . ? C2B C1B C6B 117.8(2) . . ? C3B C2B C1B 121.3(3) . . ? C2B C3B C4B 119.6(3) . . ? C5B C4B C3B 121.4(2) . . ? C5B C4B N3B 119.4(3) . . ? C3B C4B N3B 119.1(3) . . ? C4B C5B C6B 120.3(3) . . ? C5B C6B C1B 119.5(2) . . ? C5B C6B C7B 115.9(2) . . ? C1B C6B C7B 124.4(2) . . ? N1B C7B C6B 128.3(3) . . ? N1B C8B C10B 110.3(2) . . ? N1B C8B C9B 108.6(3) . . ? C10B C8B C9B 114.3(3) . . ? C15B C10B C11B 117.5(3) . . ? C15B C10B C8B 119.2(2) . . ? C11B C10B C8B 123.3(3) . . ? C10B C11B C12B 120.6(3) . . ? C13B C12B C11B 120.5(3) . . ? C14B C13B C12B 119.8(3) . . ? C13B C14B C15B 119.9(3) . . ? C10B C15B C14B 121.5(3) . . ? O2B C16B C17B 118.1(3) . . ? O2B C16B C21B 124.1(3) . . ? C17B C16B C21B 117.7(2) . . ? C18B C17B C16B 122.1(3) . . ? C17B C18B C19B 118.7(3) . . ? C20B C19B C18B 121.3(3) . . ? C20B C19B N4B 119.1(3) . . ? C18B C19B N4B 119.7(3) . . ? C19B C20B C21B 121.0(3) . . ? C20B C21B C16B 119.1(3) . . ? C20B C21B C22B 115.2(3) . . ? C16B C21B C22B 125.7(2) . . ? N2B C22B C21B 127.0(3) . . ? N2B C23B C25B 108.5(2) . . ? N2B C23B C24B 116.3(3) . . ? C25B C23B C24B 111.7(3) . . ? C26B C25B C30B 118.3(3) . . ? C26B C25B C23B 121.3(3) . . ? C30B C25B C23B 120.4(3) . . ? C25B C26B C27B 119.6(3) . . ? C28B C27B C26B 120.1(4) . . ? C29B C28B C27B 119.8(4) . . ? C28B C29B C30B 120.6(4) . . ? C29B C30B C25B 121.6(4) . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.317 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.040 #======END data_dl627_3 _database_code_CSD 165068 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Cl4 N2 O2 Zn' _chemical_formula_weight 651.68 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 13.928(2) _cell_length_b 10.9494(19) _cell_length_c 10.2078(18) _cell_angle_alpha 90.00 _cell_angle_beta 118.246(3) _cell_angle_gamma 90.00 _cell_volume 1371.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.318 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6932 _exptl_absorpt_correction_T_max 0.6932 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 2905 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 22.48 _reflns_number_total 1686 _reflns_number_gt 1551 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 1686 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.1993 _refine_ls_goodness_of_fit_ref 1.514 _refine_ls_restrained_S_all 1.514 _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 Zn Zn 0.0000 0.60393(10) 0.0000 0.0409(6) Uani 1 2 d S . . O1 O -0.1412(6) 0.6778(7) -0.1067(8) 0.0455(18) Uani 1 1 d . . . N1 N -0.0395(7) 0.5156(8) 0.1405(10) 0.047(2) Uani 1 1 d . . . Cl1 Cl -0.3315(2) 0.7647(3) -0.3696(3) 0.0568(9) Uani 1 1 d . . . Cl2 Cl -0.5478(2) 0.4318(4) -0.2196(4) 0.0749(11) Uani 1 1 d . . . C1 C -0.2305(8) 0.6196(11) -0.1263(10) 0.040(3) Uani 1 1 d . . . C2 C -0.3324(9) 0.6555(10) -0.2458(12) 0.041(3) Uani 1 1 d . . . C3 C -0.4290(7) 0.5981(13) -0.2736(11) 0.046(2) Uani 1 1 d . . . H3A H -0.4942 0.6215 -0.3549 0.055 Uiso 1 1 calc R . . C4 C -0.4285(8) 0.5068(11) -0.1812(13) 0.049(3) Uani 1 1 d . . . C5 C -0.3314(8) 0.4743(10) -0.0595(12) 0.050(3) Uani 1 1 d . . . H5A H -0.3318 0.4150 0.0055 0.060 Uiso 1 1 calc R . . C6 C -0.2341(8) 0.5272(9) -0.0317(11) 0.037(2) Uani 1 1 d . . . C7 C -0.1387(9) 0.4898(10) 0.1019(12) 0.044(3) Uani 1 1 d . . . H7A H -0.1509 0.4412 0.1673 0.053 Uiso 1 1 calc R . . C8 C 0.0429(8) 0.4750(10) 0.2961(10) 0.042(3) Uani 1 1 d . . . H8A H 0.0050 0.4241 0.3361 0.050 Uiso 1 1 calc R . . C9 C 0.0865(10) 0.5875(13) 0.3942(12) 0.058(3) Uani 1 1 d . . . H9A H 0.0269 0.6320 0.3938 0.087 Uiso 1 1 calc R . . H9B H 0.1239 0.6387 0.3567 0.087 Uiso 1 1 calc R . . H9C H 0.1360 0.5629 0.4940 0.087 Uiso 1 1 calc R . . C10 C 0.1298(9) 0.3978(9) 0.2868(12) 0.043(3) Uani 1 1 d . . . C11 C 0.0957(11) 0.3007(11) 0.1913(15) 0.067(4) Uani 1 1 d . . . H11A H 0.0216 0.2838 0.1373 0.081 Uiso 1 1 calc R . . C12 C 0.1702(12) 0.2266(12) 0.1735(16) 0.069(4) Uani 1 1 d . . . H12A H 0.1456 0.1633 0.1045 0.083 Uiso 1 1 calc R . . C13 C 0.2815(12) 0.2474(14) 0.2592(16) 0.072(4) Uani 1 1 d . . . H13A H 0.3319 0.1984 0.2487 0.086 Uiso 1 1 calc R . . C14 C 0.3150(10) 0.3413(12) 0.3591(14) 0.061(3) Uani 1 1 d . . . H14A H 0.3892 0.3548 0.4189 0.073 Uiso 1 1 calc R . . C15 C 0.2392(9) 0.4184(10) 0.3736(13) 0.049(3) Uani 1 1 d . . . H15A H 0.2634 0.4825 0.4414 0.059 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0176(9) 0.0479(10) 0.0358(9) 0.000 -0.0048(6) 0.000 O1 0.020(4) 0.049(4) 0.045(4) 0.011(4) -0.002(3) -0.002(3) N1 0.016(5) 0.049(6) 0.043(5) -0.018(4) -0.012(4) -0.002(4) Cl1 0.0383(17) 0.0584(19) 0.0463(17) 0.0152(15) -0.0025(13) 0.0116(14) Cl2 0.0268(18) 0.098(3) 0.073(2) -0.009(2) 0.0013(16) -0.0231(17) C1 0.022(5) 0.054(7) 0.033(5) -0.007(6) 0.004(4) 0.000(5) C2 0.025(6) 0.047(6) 0.039(6) 0.000(5) 0.004(5) 0.003(5) C3 0.022(5) 0.055(6) 0.040(5) 0.004(7) -0.003(4) 0.009(6) C4 0.011(5) 0.069(7) 0.047(6) -0.005(6) -0.003(5) -0.006(5) C5 0.032(7) 0.048(7) 0.046(6) -0.004(6) 0.000(5) -0.003(5) C6 0.030(6) 0.036(6) 0.035(6) -0.007(5) 0.008(5) 0.000(5) C7 0.039(7) 0.043(6) 0.030(5) 0.000(5) 0.000(5) 0.000(5) C8 0.029(6) 0.051(7) 0.023(5) 0.015(5) -0.006(4) 0.012(5) C9 0.052(7) 0.068(9) 0.041(6) -0.005(7) 0.010(5) 0.012(7) C10 0.033(7) 0.037(6) 0.038(6) 0.009(5) 0.000(5) 0.000(5) C11 0.044(8) 0.046(7) 0.059(9) -0.008(6) -0.018(7) 0.001(6) C12 0.073(10) 0.046(8) 0.071(9) -0.006(7) 0.019(8) 0.011(7) C13 0.068(10) 0.063(9) 0.069(9) 0.014(8) 0.019(8) 0.024(7) C14 0.033(7) 0.063(9) 0.058(8) 0.019(7) -0.002(6) 0.019(6) C15 0.029(6) 0.047(7) 0.047(7) 0.004(5) -0.001(5) 0.003(5) _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 Zn O1 1.918(7) 2 ? Zn O1 1.918(7) . ? Zn N1 2.010(10) 2 ? Zn N1 2.010(10) . ? O1 C1 1.326(12) . ? N1 C7 1.277(14) . ? N1 C8 1.520(13) . ? Cl1 C2 1.744(11) . ? Cl2 C4 1.724(11) . ? C1 C6 1.415(15) . ? C1 C2 1.420(15) . ? C2 C3 1.388(16) . ? C3 C4 1.372(17) . ? C4 C5 1.382(16) . ? C5 C6 1.374(15) . ? C6 C7 1.441(15) . ? C8 C10 1.515(15) . ? C8 C9 1.521(17) . ? C10 C11 1.366(17) . ? C10 C15 1.372(15) . ? C11 C12 1.396(19) . ? C12 C13 1.39(2) . ? C13 C14 1.37(2) . ? C14 C15 1.412(16) . ? 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 O1 Zn O1 130.1(4) 2 . ? O1 Zn N1 93.1(3) 2 2 ? O1 Zn N1 110.5(3) . 2 ? O1 Zn N1 110.5(3) 2 . ? O1 Zn N1 93.1(3) . . ? N1 Zn N1 122.5(5) 2 . ? C1 O1 Zn 121.3(6) . . ? C7 N1 C8 115.4(10) . . ? C7 N1 Zn 120.5(8) . . ? C8 N1 Zn 124.0(7) . . ? O1 C1 C6 125.0(8) . . ? O1 C1 C2 118.8(9) . . ? C6 C1 C2 116.1(9) . . ? C3 C2 C1 121.9(10) . . ? C3 C2 Cl1 120.0(8) . . ? C1 C2 Cl1 117.8(8) . . ? C4 C3 C2 120.0(9) . . ? C3 C4 C5 119.4(10) . . ? C3 C4 Cl2 120.0(8) . . ? C5 C4 Cl2 120.6(10) . . ? C6 C5 C4 121.8(11) . . ? C5 C6 C1 120.7(10) . . ? C5 C6 C7 116.9(10) . . ? C1 C6 C7 122.3(9) . . ? N1 C7 C6 127.4(10) . . ? C10 C8 N1 109.2(9) . . ? C10 C8 C9 114.3(9) . . ? N1 C8 C9 108.6(9) . . ? C11 C10 C15 119.5(12) . . ? C11 C10 C8 117.4(10) . . ? C15 C10 C8 123.0(10) . . ? C10 C11 C12 121.1(12) . . ? C13 C12 C11 119.9(13) . . ? C14 C13 C12 118.6(13) . . ? C13 C14 C15 121.3(12) . . ? C10 C15 C14 119.4(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.510 _refine_diff_density_min -1.371 _refine_diff_density_rms 0.177 #======END data_cce1_4 _database_code_CSD 165069 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N2 O4 Zn' _chemical_formula_weight 573.97 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 17.5693(17) _cell_length_b 8.7580(8) _cell_length_c 11.9812(11) _cell_angle_alpha 90.00 _cell_angle_beta 130.2830(10) _cell_angle_gamma 90.00 _cell_volume 1406.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.913 _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 298(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 4552 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.93 _reflns_number_total 2434 _reflns_number_gt 2205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(10) _refine_ls_number_reflns 2434 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 0.657 _refine_ls_restrained_S_all 0.657 _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 Zn Zn 0.0000 0.8413 0.0000 0.04585(13) Uani 1 2 d S . . O1 O 0.01347(14) 0.9550(2) 0.1484(2) 0.0527(4) Uani 1 1 d . . . O2 O 0.23207(17) 0.7826(3) 0.7263(2) 0.0713(6) Uani 1 1 d . . . N1 N 0.13143(14) 0.7301(3) 0.1360(2) 0.0462(5) Uani 1 1 d . . . C1 C 0.07133(17) 0.9098(3) 0.2857(3) 0.0448(5) Uani 1 1 d . . . C2 C 0.05743(18) 0.9781(3) 0.3793(3) 0.0511(6) Uani 1 1 d . . . H2A H 0.0104 1.0555 0.3425 0.061 Uiso 1 1 calc R . . C3 C 0.11110(18) 0.9335(4) 0.5213(3) 0.0538(6) Uani 1 1 d . . . H3A H 0.0995 0.9802 0.5788 0.065 Uiso 1 1 calc R . . C4 C 0.18331(17) 0.8188(5) 0.5817(3) 0.0526(7) Uani 1 1 d . . . C5 C 0.20221(18) 0.7548(4) 0.4972(3) 0.0509(6) Uani 1 1 d . . . H5A H 0.2524 0.6821 0.5380 0.061 Uiso 1 1 calc R . . C6 C 0.14641(16) 0.7977(3) 0.3486(2) 0.0451(6) Uani 1 1 d . . . C7 C 0.17482(17) 0.7217(3) 0.2731(3) 0.0485(5) Uani 1 1 d . . . H7A H 0.2309 0.6595 0.3301 0.058 Uiso 1 1 calc R . . C8 C 0.18411(19) 0.6542(4) 0.0920(3) 0.0606(8) Uani 1 1 d . . . H8A H 0.2269 0.5741 0.1637 0.073 Uiso 1 1 calc R . . C9 C 0.2504(3) 0.7724(8) 0.0996(6) 0.130(3) Uani 1 1 d . . . H9A H 0.2956 0.8140 0.1967 0.195 Uiso 1 1 calc R . . H9B H 0.2099 0.8528 0.0311 0.195 Uiso 1 1 calc R . . H9C H 0.2878 0.7252 0.0760 0.195 Uiso 1 1 calc R . . C10 C 0.10998(17) 0.5793(3) -0.0579(3) 0.0469(5) Uani 1 1 d . . . C11 C 0.0649(3) 0.4460(5) -0.0687(4) 0.0720(9) Uani 1 1 d . . . H11A H 0.0777 0.4078 0.0145 0.086 Uiso 1 1 calc R . . C12 C 0.0012(3) 0.3663(7) -0.1981(6) 0.1043(17) Uani 1 1 d . . . H12A H -0.0269 0.2743 -0.2019 0.125 Uiso 1 1 calc R . . C13 C -0.0198(3) 0.4261(8) -0.3211(5) 0.1083(19) Uani 1 1 d . . . H13A H -0.0638 0.3757 -0.4102 0.130 Uiso 1 1 calc R . . C14 C 0.0230(4) 0.5570(7) -0.3132(4) 0.0995(17) Uani 1 1 d . . . H14A H 0.0082 0.5964 -0.3974 0.119 Uiso 1 1 calc R . . C15 C 0.0894(3) 0.6351(4) -0.1811(4) 0.0670(8) Uani 1 1 d . . . H15A H 0.1195 0.7248 -0.1772 0.080 Uiso 1 1 calc R . . C16 C 0.2869(3) 0.6471(6) 0.7801(4) 0.0843(11) Uani 1 1 d . . . H16A H 0.3169 0.6344 0.8807 0.126 Uiso 1 1 calc R . . H16B H 0.3381 0.6513 0.7727 0.126 Uiso 1 1 calc R . . H16C H 0.2434 0.5625 0.7238 0.126 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.04297(18) 0.0494(2) 0.04704(19) 0.000 0.02993(15) 0.000 O1 0.0547(9) 0.0534(11) 0.0545(10) 0.0021(8) 0.0372(8) 0.0090(8) O2 0.0819(13) 0.0831(17) 0.0528(10) 0.0017(10) 0.0453(10) 0.0109(11) N1 0.0416(9) 0.0500(12) 0.0524(10) -0.0084(9) 0.0329(9) -0.0001(9) C1 0.0423(11) 0.0458(13) 0.0512(12) -0.0077(10) 0.0324(10) -0.0061(10) C2 0.0483(12) 0.0503(15) 0.0633(15) -0.0067(11) 0.0400(12) 0.0007(10) C3 0.0503(12) 0.0637(18) 0.0552(13) -0.0161(12) 0.0376(12) -0.0083(12) C4 0.0505(10) 0.061(2) 0.0487(10) -0.0040(13) 0.0332(9) -0.0019(14) C5 0.0467(11) 0.0554(16) 0.0515(13) -0.0007(11) 0.0321(11) 0.0051(11) C6 0.0434(11) 0.0488(16) 0.0491(11) -0.0051(9) 0.0325(10) -0.0018(9) C7 0.0400(10) 0.0524(15) 0.0510(12) -0.0027(11) 0.0285(10) 0.0066(10) C8 0.0438(12) 0.082(2) 0.0608(14) -0.0202(15) 0.0360(12) -0.0001(13) C9 0.115(3) 0.176(6) 0.169(4) -0.107(4) 0.124(3) -0.086(3) C10 0.0461(11) 0.0525(14) 0.0520(12) -0.0003(11) 0.0362(10) 0.0078(10) C11 0.080(2) 0.073(2) 0.079(2) -0.0113(17) 0.0589(18) -0.0147(17) C12 0.092(2) 0.094(4) 0.134(3) -0.050(3) 0.076(2) -0.037(3) C13 0.079(2) 0.134(5) 0.071(2) -0.039(3) 0.0302(19) 0.021(3) C14 0.115(3) 0.128(4) 0.0511(17) 0.019(2) 0.052(2) 0.059(3) C15 0.086(2) 0.0643(19) 0.0698(16) 0.0157(15) 0.0587(16) 0.0226(16) C16 0.103(3) 0.091(3) 0.0663(18) 0.0179(19) 0.0581(19) 0.027(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 Zn O1 1.9139(19) . ? Zn O1 1.9139(19) 2 ? Zn N1 2.017(2) 2 ? Zn N1 2.017(2) . ? O1 C1 1.317(3) . ? O2 C4 1.384(3) . ? O2 C16 1.396(5) . ? N1 C7 1.291(3) . ? N1 C8 1.486(3) . ? C1 C6 1.409(4) . ? C1 C2 1.424(3) . ? C2 C3 1.365(4) . ? C3 C4 1.398(4) . ? C4 C5 1.373(4) . ? C5 C6 1.420(3) . ? C6 C7 1.448(3) . ? C8 C9 1.516(6) . ? C8 C10 1.526(4) . ? C10 C15 1.364(4) . ? C10 C11 1.370(5) . ? C11 C12 1.379(6) . ? C12 C13 1.371(7) . ? C13 C14 1.340(8) . ? C14 C15 1.395(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 O1 Zn O1 117.32(13) . 2 ? O1 Zn N1 113.00(8) . 2 ? O1 Zn N1 96.40(8) 2 2 ? O1 Zn N1 96.40(8) . . ? O1 Zn N1 113.00(8) 2 . ? N1 Zn N1 122.28(13) 2 . ? C1 O1 Zn 122.41(17) . . ? C4 O2 C16 117.2(3) . . ? C7 N1 C8 115.8(2) . . ? C7 N1 Zn 118.76(16) . . ? C8 N1 Zn 125.44(17) . . ? O1 C1 C6 125.3(2) . . ? O1 C1 C2 118.0(2) . . ? C6 C1 C2 116.7(2) . . ? C3 C2 C1 122.0(3) . . ? C2 C3 C4 121.0(2) . . ? C5 C4 O2 125.5(3) . . ? C5 C4 C3 118.9(3) . . ? O2 C4 C3 115.7(2) . . ? C4 C5 C6 121.1(3) . . ? C1 C6 C5 120.3(2) . . ? C1 C6 C7 124.6(2) . . ? C5 C6 C7 115.1(2) . . ? N1 C7 C6 127.6(2) . . ? N1 C8 C9 107.7(3) . . ? N1 C8 C10 110.89(19) . . ? C9 C8 C10 113.7(3) . . ? C15 C10 C11 118.2(3) . . ? C15 C10 C8 123.2(3) . . ? C11 C10 C8 118.6(3) . . ? C10 C11 C12 122.5(4) . . ? C13 C12 C11 118.3(5) . . ? C14 C13 C12 120.1(4) . . ? C13 C14 C15 121.3(4) . . ? C10 C15 C14 119.6(4) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 28.93 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.294 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.041