data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Patrick Guiry' _publ_contact_author_name 'Patrick Guiry' _publ_contact_author_email P.GUIRY@UCD.IE _publ_section_title ; The Synthesis of New Oxazoline-Containing Bifunctional Catalysts and their Application in the Addition of Diethylzinc to Aldehydes ; # Attachment 'gui41-2e.cif' data_gui41 _database_code_depnum_ccdc_archive 'CCDC 713716' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N3 O' _chemical_formula_sum 'C18 H21 N3 O' _chemical_formula_weight 295.38 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.1265(4) _cell_length_b 13.8082(9) _cell_length_c 19.2305(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1626.82(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4842 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 26.91 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8422 _exptl_absorpt_correction_T_max 0.9555 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.118 before and 0.019 after correction. The Ratio of minimum to maximum transmission is 0.881406. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8732 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.09 _reflns_number_total 2067 _reflns_number_gt 1913 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0586P)^2^+0.1300P] 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 SHELXL _refine_ls_extinction_coef 0.034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2067 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4003(5) 0.5743(2) 1.15767(11) 0.0900(8) Uani 1 1 d . . . H1A H 0.5302 0.5395 1.1452 0.135 Uiso 1 1 calc R . . H1B H 0.3144 0.5358 1.1889 0.135 Uiso 1 1 calc R . . H1C H 0.4397 0.6340 1.1800 0.135 Uiso 1 1 calc R . . C2 C 0.4062(5) 0.6566(2) 1.04289(13) 0.0992(9) Uani 1 1 d . . . H2A H 0.3231 0.6720 1.0020 0.149 Uiso 1 1 calc R . . H2B H 0.5340 0.6207 1.0299 0.149 Uiso 1 1 calc R . . H2C H 0.4492 0.7154 1.0657 0.149 Uiso 1 1 calc R . . C3 C 0.0629(5) 0.6524(2) 1.11082(16) 0.1068(10) Uani 1 1 d . . . H3A H 0.1031 0.7120 1.1331 0.160 Uiso 1 1 calc R . . H3B H -0.0253 0.6146 1.1419 0.160 Uiso 1 1 calc R . . H3C H -0.0184 0.6663 1.0693 0.160 Uiso 1 1 calc R . . C4 C 0.2675(3) 0.59611(14) 1.09206(9) 0.0600(4) Uani 1 1 d . . . C5 C 0.2122(3) 0.50022(14) 1.05729(9) 0.0601(4) Uani 1 1 d . . . H5 H 0.3497 0.4679 1.0454 0.072 Uiso 1 1 calc R . . N1 N 0.0849(3) 0.51156(11) 0.99277(7) 0.0595(4) Uani 1 1 d . . . C6 C 0.0750(6) 0.42955(19) 1.09986(12) 0.0978(9) Uani 1 1 d . . . H6A H 0.1627 0.3752 1.1154 0.117 Uiso 1 1 calc R . . H6B H 0.0127 0.4615 1.1402 0.117 Uiso 1 1 calc R . . O O -0.0939(3) 0.39774(10) 1.05323(7) 0.0825(5) Uani 1 1 d . . . C7 C -0.0725(3) 0.45242(11) 0.99508(8) 0.0517(4) Uani 1 1 d . . . C8 C -0.2385(3) 0.43554(11) 0.94152(8) 0.0486(4) Uani 1 1 d . . . C9 C -0.3999(3) 0.36626(12) 0.95376(9) 0.0575(4) Uani 1 1 d . . . H9 H -0.3958 0.3307 0.9948 0.069 Uiso 1 1 calc R . . C10 C -0.5639(4) 0.34909(14) 0.90710(10) 0.0645(5) Uani 1 1 d . . . H10 H -0.6704 0.3029 0.9163 0.077 Uiso 1 1 calc R . . C11 C -0.5683(4) 0.40149(14) 0.84624(10) 0.0652(5) Uani 1 1 d . . . H11 H -0.6806 0.3911 0.8146 0.078 Uiso 1 1 calc R . . C12 C -0.4097(4) 0.46907(13) 0.83132(9) 0.0602(4) Uani 1 1 d . . . H12 H -0.4153 0.5027 0.7894 0.072 Uiso 1 1 calc R . . C13 C -0.2405(3) 0.48795(11) 0.87818(8) 0.0501(4) Uani 1 1 d . . . N2 N -0.0746(3) 0.55342(12) 0.86623(7) 0.0608(4) Uani 1 1 d . . . H1N2 H 0.019(4) 0.5567(15) 0.8989(10) 0.066(6) Uiso 1 1 d . . . C14 C -0.0298(3) 0.61222(12) 0.80983(8) 0.0512(4) Uani 1 1 d . . . C15 C 0.1737(3) 0.65772(14) 0.80823(9) 0.0603(4) Uani 1 1 d . . . H15 H 0.2746 0.6476 0.8436 0.072 Uiso 1 1 calc R . . C16 C 0.2216(4) 0.71737(14) 0.75376(9) 0.0649(5) Uani 1 1 d . . . H16 H 0.3561 0.7485 0.7517 0.078 Uiso 1 1 calc R . . C17 C 0.0703(4) 0.73119(13) 0.70207(10) 0.0660(5) Uani 1 1 d . . . H17 H 0.0986 0.7720 0.6647 0.079 Uiso 1 1 calc R . . C18 C -0.1223(4) 0.68303(14) 0.70761(10) 0.0683(5) Uani 1 1 d . . . H18 H -0.2237 0.6914 0.6721 0.082 Uiso 1 1 calc R . . N3 N -0.1775(3) 0.62421(11) 0.76041(8) 0.0623(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0985(17) 0.1064(17) 0.0649(12) -0.0032(12) -0.0279(13) -0.0180(17) C2 0.1030(18) 0.1085(18) 0.0861(15) 0.0138(14) -0.0117(16) -0.0403(18) C3 0.0937(18) 0.1068(19) 0.120(2) -0.0369(18) -0.0003(19) 0.0225(18) C4 0.0596(10) 0.0665(10) 0.0538(9) -0.0036(8) -0.0034(8) -0.0004(9) C5 0.0662(11) 0.0664(10) 0.0477(8) 0.0010(7) -0.0112(8) 0.0068(9) N1 0.0654(9) 0.0712(9) 0.0420(6) 0.0031(6) -0.0063(7) -0.0082(8) C6 0.135(2) 0.0880(15) 0.0700(12) 0.0268(12) -0.0461(16) -0.0341(17) O 0.1173(12) 0.0702(8) 0.0601(7) 0.0236(6) -0.0301(9) -0.0291(9) C7 0.0685(10) 0.0445(7) 0.0421(7) 0.0004(6) -0.0014(8) 0.0045(8) C8 0.0616(9) 0.0416(7) 0.0427(7) -0.0041(6) 0.0007(7) 0.0018(7) C9 0.0778(12) 0.0468(8) 0.0479(8) -0.0017(7) 0.0014(9) -0.0040(9) C10 0.0752(12) 0.0554(9) 0.0628(10) -0.0056(8) 0.0009(10) -0.0155(10) C11 0.0698(11) 0.0646(10) 0.0613(10) -0.0045(8) -0.0142(10) -0.0087(10) C12 0.0718(11) 0.0577(9) 0.0512(8) 0.0038(8) -0.0113(9) -0.0038(9) C13 0.0592(9) 0.0453(7) 0.0457(7) -0.0016(6) -0.0023(7) 0.0019(7) N2 0.0673(9) 0.0698(9) 0.0452(7) 0.0108(7) -0.0129(7) -0.0128(9) C14 0.0632(10) 0.0482(8) 0.0421(7) -0.0001(6) 0.0004(7) 0.0028(8) C15 0.0633(10) 0.0673(10) 0.0502(8) 0.0017(8) -0.0020(8) -0.0030(9) C16 0.0692(11) 0.0666(10) 0.0590(10) 0.0002(8) 0.0108(9) -0.0074(10) C17 0.0902(14) 0.0570(9) 0.0509(9) 0.0086(8) 0.0105(11) 0.0011(11) C18 0.0838(14) 0.0642(10) 0.0570(10) 0.0145(9) -0.0115(10) 0.0017(10) N3 0.0686(9) 0.0622(8) 0.0562(8) 0.0128(7) -0.0095(8) -0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.531(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.521(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.519(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.521(3) . ? C5 N1 1.474(2) . ? C5 C6 1.526(3) . ? C5 H5 0.9800 . ? N1 C7 1.265(2) . ? C6 O 1.438(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O C7 1.3557(19) . ? C7 C8 1.466(2) . ? C8 C9 1.396(3) . ? C8 C13 1.417(2) . ? C9 C10 1.368(3) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C13 1.398(3) . ? C12 H12 0.9300 . ? C13 N2 1.379(2) . ? N2 C14 1.382(2) . ? N2 H1N2 0.85(2) . ? C14 N3 1.323(2) . ? C14 C15 1.396(3) . ? C15 C16 1.365(3) . ? C15 H15 0.9300 . ? C16 C17 1.373(3) . ? C16 H16 0.9300 . ? C17 C18 1.359(3) . ? C17 H17 0.9300 . ? C18 N3 1.344(2) . ? C18 H18 0.9300 . ? 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C4 C2 109.1(2) . . ? C3 C4 C5 111.49(19) . . ? C2 C4 C5 109.23(17) . . ? C3 C4 C1 110.09(19) . . ? C2 C4 C1 108.87(19) . . ? C5 C4 C1 108.02(17) . . ? N1 C5 C4 113.28(15) . . ? N1 C5 C6 103.17(17) . . ? C4 C5 C6 116.32(17) . . ? N1 C5 H5 107.9 . . ? C4 C5 H5 107.9 . . ? C6 C5 H5 107.9 . . ? C7 N1 C5 107.78(14) . . ? O C6 C5 104.90(15) . . ? O C6 H6A 110.8 . . ? C5 C6 H6A 110.8 . . ? O C6 H6B 110.8 . . ? C5 C6 H6B 110.8 . . ? H6A C6 H6B 108.8 . . ? C7 O C6 105.96(16) . . ? N1 C7 O 117.54(16) . . ? N1 C7 C8 127.38(14) . . ? O C7 C8 115.08(16) . . ? C9 C8 C13 119.29(15) . . ? C9 C8 C7 118.81(14) . . ? C13 C8 C7 121.90(15) . . ? C10 C9 C8 121.90(16) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 118.79(19) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C12 121.28(19) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 121.01(16) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? N2 C13 C12 124.13(15) . . ? N2 C13 C8 118.16(15) . . ? C12 C13 C8 117.70(16) . . ? C13 N2 C14 131.46(16) . . ? C13 N2 H1N2 114.0(14) . . ? C14 N2 H1N2 114.5(14) . . ? N3 C14 N2 120.08(17) . . ? N3 C14 C15 122.59(16) . . ? N2 C14 C15 117.32(16) . . ? C16 C15 C14 118.74(18) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 119.63(19) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 117.49(16) . . ? C18 C17 H17 121.3 . . ? C16 C17 H17 121.3 . . ? N3 C18 C17 125.02(19) . . ? N3 C18 H18 117.5 . . ? C17 C18 H18 117.5 . . ? C14 N3 C18 116.52(17) . . ? 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 C3 C4 C5 N1 59.3(2) . . . . ? C2 C4 C5 N1 -61.3(2) . . . . ? C1 C4 C5 N1 -179.59(18) . . . . ? C3 C4 C5 C6 -60.0(3) . . . . ? C2 C4 C5 C6 179.4(2) . . . . ? C1 C4 C5 C6 61.1(2) . . . . ? C4 C5 N1 C7 -132.92(18) . . . . ? C6 C5 N1 C7 -6.3(2) . . . . ? N1 C5 C6 O 7.9(3) . . . . ? C4 C5 C6 O 132.6(2) . . . . ? C5 C6 O C7 -6.9(3) . . . . ? C5 N1 C7 O 2.2(2) . . . . ? C5 N1 C7 C8 -177.92(16) . . . . ? C6 O C7 N1 3.2(3) . . . . ? C6 O C7 C8 -176.62(19) . . . . ? N1 C7 C8 C9 179.71(17) . . . . ? O C7 C8 C9 -0.4(2) . . . . ? N1 C7 C8 C13 -0.8(3) . . . . ? O C7 C8 C13 179.08(15) . . . . ? C13 C8 C9 C10 -1.7(3) . . . . ? C7 C8 C9 C10 177.80(17) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 N2 178.96(18) . . . . ? C11 C12 C13 C8 -0.3(3) . . . . ? C9 C8 C13 N2 -177.63(16) . . . . ? C7 C8 C13 N2 2.8(2) . . . . ? C9 C8 C13 C12 1.7(2) . . . . ? C7 C8 C13 C12 -177.86(16) . . . . ? C12 C13 N2 C14 -1.1(3) . . . . ? C8 C13 N2 C14 178.11(18) . . . . ? C13 N2 C14 N3 12.1(3) . . . . ? C13 N2 C14 C15 -168.46(18) . . . . ? N3 C14 C15 C16 0.4(3) . . . . ? N2 C14 C15 C16 -179.04(17) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C16 C17 C18 N3 1.2(3) . . . . ? N2 C14 N3 C18 179.50(17) . . . . ? C15 C14 N3 C18 0.1(3) . . . . ? C17 C18 N3 C14 -0.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H1N2 N1 0.85(2) 1.95(2) 2.685(2) 143.6(19) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.151 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.031 # Attachment 'gui43-2eZnCl2.cif' data_gui43 _database_code_depnum_ccdc_archive 'CCDC 713717' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N3 O Cl2 Zn' _chemical_formula_sum 'C18 H21 N3 O Cl2 Zn' _chemical_formula_weight 431.65 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4417(6) _cell_length_b 11.1428(6) _cell_length_c 17.0180(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1980.04(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8792 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.521 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4704 _exptl_absorpt_correction_T_max 0.6583 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.056 before and 0.020 after correction. The Ratio of minimum to maximum transmission is 0.714605. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13618 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 29.05 _reflns_number_total 4783 _reflns_number_gt 4563 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0436P)^2^+0.4825P] 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 -0.005(9) _refine_ls_number_reflns 4783 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.77926(2) 0.52031(2) 0.141345(13) 0.04437(8) Uani 1 1 d . . . Cl1 Cl 0.81902(8) 0.71506(6) 0.12102(6) 0.0841(3) Uani 1 1 d . . . Cl2 Cl 0.62576(7) 0.44024(10) 0.06696(4) 0.0831(3) Uani 1 1 d . . . C1 C 0.4833(3) 0.4548(3) 0.3030(3) 0.0889(11) Uani 1 1 d . . . H1A H 0.3955 0.4804 0.3017 0.133 Uiso 1 1 calc R . . H1B H 0.4939 0.3944 0.3426 0.133 Uiso 1 1 calc R . . H1C H 0.5065 0.4224 0.2527 0.133 Uiso 1 1 calc R . . C2 C 0.5520(4) 0.6562(3) 0.2591(2) 0.0894(11) Uani 1 1 d . . . H2A H 0.5623 0.6207 0.2081 0.134 Uiso 1 1 calc R . . H2B H 0.6154 0.7176 0.2664 0.134 Uiso 1 1 calc R . . H2C H 0.4681 0.6908 0.2632 0.134 Uiso 1 1 calc R . . C3 C 0.5339(5) 0.6149(3) 0.4016(2) 0.0999(14) Uani 1 1 d . . . H3A H 0.4448 0.6361 0.4022 0.150 Uiso 1 1 calc R . . H3B H 0.5847 0.6854 0.4105 0.150 Uiso 1 1 calc R . . H3C H 0.5506 0.5572 0.4422 0.150 Uiso 1 1 calc R . . C4 C 0.5681(3) 0.5608(2) 0.32165(17) 0.0599(6) Uani 1 1 d . . . C5 C 0.7104(2) 0.5233(2) 0.32629(12) 0.0497(5) Uani 1 1 d . . . H5 H 0.7621 0.5950 0.3367 0.060 Uiso 1 1 calc R . . N1 N 0.75937(16) 0.46467(15) 0.25407(9) 0.0403(3) Uani 1 1 d . . . C6 C 0.7398(3) 0.4293(3) 0.38951(13) 0.0660(7) Uani 1 1 d . . . H6A H 0.7951 0.4626 0.4298 0.079 Uiso 1 1 calc R . . H6B H 0.6615 0.4011 0.4140 0.079 Uiso 1 1 calc R . . O O 0.8033(2) 0.33281(16) 0.34854(9) 0.0595(4) Uani 1 1 d . . . C7 C 0.8065(2) 0.36365(18) 0.27249(11) 0.0404(4) Uani 1 1 d . . . C8 C 0.8606(2) 0.27162(18) 0.22000(12) 0.0398(4) Uani 1 1 d . . . C9 C 0.8428(2) 0.1517(2) 0.24027(14) 0.0494(5) Uani 1 1 d . . . H9 H 0.8012 0.1328 0.2870 0.059 Uiso 1 1 calc R . . C10 C 0.8856(3) 0.0605(2) 0.19228(17) 0.0570(6) Uani 1 1 d . . . H10 H 0.8736 -0.0193 0.2065 0.068 Uiso 1 1 calc R . . C11 C 0.9465(3) 0.0890(2) 0.12295(16) 0.0566(6) Uani 1 1 d . . . H11 H 0.9744 0.0279 0.0899 0.068 Uiso 1 1 calc R . . C12 C 0.9665(2) 0.2076(2) 0.10203(15) 0.0517(5) Uani 1 1 d . . . H12 H 1.0081 0.2250 0.0551 0.062 Uiso 1 1 calc R . . C13 C 0.92527(19) 0.30162(18) 0.15020(12) 0.0401(4) Uani 1 1 d . . . N2 N 0.94193(17) 0.42254(16) 0.12784(10) 0.0407(3) Uani 1 1 d . . . C14 C 1.0564(2) 0.4585(2) 0.10277(12) 0.0427(4) Uani 1 1 d . . . C15 C 1.1749(3) 0.3976(2) 0.11044(19) 0.0620(7) Uani 1 1 d . . . H15 H 1.1782 0.3234 0.1354 0.074 Uiso 1 1 calc R . . C16 C 1.2843(3) 0.4480(3) 0.0813(2) 0.0846(11) Uani 1 1 d . . . H16 H 1.3615 0.4071 0.0867 0.102 Uiso 1 1 calc R . . C17 C 1.2833(3) 0.5586(3) 0.0437(2) 0.0845(11) Uani 1 1 d . . . H17 H 1.3580 0.5904 0.0224 0.101 Uiso 1 1 calc R . . C18 C 1.1722(3) 0.6186(3) 0.03891(16) 0.0651(8) Uani 1 1 d . . . H18 H 1.1695 0.6937 0.0151 0.078 Uiso 1 1 calc R . . N3 N 1.0636(2) 0.5694(2) 0.06889(11) 0.0478(4) Uani 1 1 d . . . H1N3 H 1.009(3) 0.604(2) 0.0670(16) 0.034(7) 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 Zn 0.03839(12) 0.05278(13) 0.04193(12) 0.01340(10) -0.00095(9) 0.00211(10) Cl1 0.0716(4) 0.0541(3) 0.1267(7) 0.0365(4) 0.0193(4) 0.0117(3) Cl2 0.0498(3) 0.1487(8) 0.0508(3) 0.0064(4) -0.0100(3) -0.0247(4) C1 0.0559(16) 0.072(2) 0.139(3) -0.014(2) 0.0138(19) -0.0048(15) C2 0.085(2) 0.0709(19) 0.112(3) 0.0242(19) 0.025(2) 0.0329(18) C3 0.137(4) 0.0652(19) 0.097(3) -0.0156(18) 0.064(3) 0.005(2) C4 0.0663(15) 0.0416(11) 0.0717(15) -0.0045(11) 0.0247(13) 0.0043(11) C5 0.0616(13) 0.0450(9) 0.0424(9) -0.0083(8) 0.0089(9) -0.0072(11) N1 0.0444(9) 0.0419(8) 0.0347(7) -0.0007(6) 0.0022(6) 0.0005(7) C6 0.090(2) 0.0718(15) 0.0359(10) -0.0032(10) 0.0064(12) 0.0061(15) O 0.0870(12) 0.0582(9) 0.0334(7) 0.0093(6) 0.0030(8) 0.0123(9) C7 0.0448(10) 0.0442(10) 0.0321(8) 0.0034(7) -0.0005(7) -0.0027(8) C8 0.0412(10) 0.0409(9) 0.0373(9) 0.0020(8) -0.0030(8) 0.0012(8) C9 0.0524(12) 0.0468(11) 0.0491(11) 0.0058(9) 0.0019(9) -0.0009(10) C10 0.0605(14) 0.0390(10) 0.0714(15) -0.0008(10) -0.0018(12) -0.0004(10) C11 0.0563(13) 0.0472(12) 0.0664(15) -0.0150(11) 0.0027(11) 0.0008(10) C12 0.0538(12) 0.0533(12) 0.0481(12) -0.0090(10) 0.0060(10) -0.0032(10) C13 0.0376(9) 0.0436(10) 0.0391(9) -0.0015(8) -0.0007(8) -0.0025(7) N2 0.0397(8) 0.0434(8) 0.0391(8) 0.0012(7) 0.0041(6) -0.0007(7) C14 0.0454(10) 0.0470(11) 0.0356(9) -0.0082(8) 0.0059(8) -0.0054(8) C15 0.0464(12) 0.0535(13) 0.0861(18) -0.0057(13) 0.0170(13) 0.0006(10) C16 0.0495(14) 0.0634(16) 0.141(3) -0.0252(17) 0.0362(19) -0.0053(13) C17 0.0692(18) 0.0737(18) 0.111(2) -0.0285(17) 0.0516(19) -0.0246(16) C18 0.0799(18) 0.0598(14) 0.0557(13) -0.0130(11) 0.0264(13) -0.0272(14) N3 0.0519(12) 0.0498(10) 0.0417(9) -0.0032(8) 0.0077(8) -0.0088(10) _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 N1 2.0267(16) . ? Zn N2 2.0310(18) . ? Zn Cl2 2.2288(7) . ? Zn Cl1 2.2363(7) . ? C1 C4 1.510(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.514(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.531(4) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.544(4) . ? C5 N1 1.483(2) . ? C5 C6 1.533(4) . ? C5 H5 0.9800 . ? N1 C7 1.268(3) . ? C6 O 1.442(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O C7 1.339(2) . ? C7 C8 1.473(3) . ? C8 C9 1.393(3) . ? C8 C13 1.407(3) . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(4) . ? C10 H10 0.9300 . ? C11 C12 1.384(4) . ? C11 H11 0.9300 . ? C12 C13 1.398(3) . ? C12 H12 0.9300 . ? C13 N2 1.411(3) . ? N2 C14 1.331(3) . ? C14 N3 1.365(3) . ? C14 C15 1.417(4) . ? C15 C16 1.366(4) . ? C15 H15 0.9300 . ? C16 C17 1.389(5) . ? C16 H16 0.9300 . ? C17 C18 1.342(5) . ? C17 H17 0.9300 . ? C18 N3 1.359(3) . ? C18 H18 0.9300 . ? N3 H1N3 0.69(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn N2 91.64(7) . . ? N1 Zn Cl2 109.96(5) . . ? N2 Zn Cl2 108.81(6) . . ? N1 Zn Cl1 117.53(6) . . ? N2 Zn Cl1 110.35(5) . . ? Cl2 Zn Cl1 115.73(4) . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C2 109.6(3) . . ? C1 C4 C3 111.0(3) . . ? C2 C4 C3 108.8(2) . . ? C1 C4 C5 111.3(2) . . ? C2 C4 C5 109.4(2) . . ? C3 C4 C5 106.6(3) . . ? N1 C5 C6 102.17(18) . . ? N1 C5 C4 114.10(19) . . ? C6 C5 C4 114.4(2) . . ? N1 C5 H5 108.6 . . ? C6 C5 H5 108.6 . . ? C4 C5 H5 108.6 . . ? C7 N1 C5 108.67(17) . . ? C7 N1 Zn 117.77(13) . . ? C5 N1 Zn 133.23(14) . . ? O C6 C5 105.22(17) . . ? O C6 H6A 110.7 . . ? C5 C6 H6A 110.7 . . ? O C6 H6B 110.7 . . ? C5 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? C7 O C6 106.69(18) . . ? N1 C7 O 117.20(19) . . ? N1 C7 C8 128.11(17) . . ? O C7 C8 114.64(18) . . ? C9 C8 C13 120.1(2) . . ? C9 C8 C7 117.81(19) . . ? C13 C8 C7 122.07(18) . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 119.2(2) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 121.2(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 117.7(2) . . ? C12 C13 N2 121.31(19) . . ? C8 C13 N2 120.92(18) . . ? C14 N2 C13 119.00(18) . . ? C14 N2 Zn 128.74(15) . . ? C13 N2 Zn 112.25(13) . . ? N2 C14 N3 117.2(2) . . ? N2 C14 C15 127.6(2) . . ? N3 C14 C15 115.1(2) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.7(3) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 118.5(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 N3 119.8(3) . . ? C17 C18 H18 120.1 . . ? N3 C18 H18 120.1 . . ? C18 N3 C14 124.8(3) . . ? C18 N3 H1N3 117(2) . . ? C14 N3 H1N3 118(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C4 C5 N1 56.8(3) . . . . ? C2 C4 C5 N1 -64.5(3) . . . . ? C3 C4 C5 N1 178.0(2) . . . . ? C1 C4 C5 C6 -60.4(3) . . . . ? C2 C4 C5 C6 178.3(3) . . . . ? C3 C4 C5 C6 60.8(3) . . . . ? C6 C5 N1 C7 -0.8(3) . . . . ? C4 C5 N1 C7 -124.9(2) . . . . ? C6 C5 N1 Zn -173.94(18) . . . . ? C4 C5 N1 Zn 62.0(3) . . . . ? N2 Zn N1 C7 -27.27(17) . . . . ? Cl2 Zn N1 C7 83.44(16) . . . . ? Cl1 Zn N1 C7 -141.30(15) . . . . ? N2 Zn N1 C5 145.33(19) . . . . ? Cl2 Zn N1 C5 -103.96(19) . . . . ? Cl1 Zn N1 C5 31.3(2) . . . . ? N1 C5 C6 O 1.6(3) . . . . ? C4 C5 C6 O 125.5(2) . . . . ? C5 C6 O C7 -1.9(3) . . . . ? C5 N1 C7 O -0.4(3) . . . . ? Zn N1 C7 O 173.95(16) . . . . ? C5 N1 C7 C8 176.8(2) . . . . ? Zn N1 C7 C8 -8.8(3) . . . . ? C6 O C7 N1 1.5(3) . . . . ? C6 O C7 C8 -176.1(2) . . . . ? N1 C7 C8 C9 -145.5(2) . . . . ? O C7 C8 C9 31.8(3) . . . . ? N1 C7 C8 C13 32.7(3) . . . . ? O C7 C8 C13 -150.1(2) . . . . ? C13 C8 C9 C10 -1.1(4) . . . . ? C7 C8 C9 C10 177.1(2) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 1.0(4) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C8 -1.1(4) . . . . ? C11 C12 C13 N2 -178.0(2) . . . . ? C9 C8 C13 C12 1.8(3) . . . . ? C7 C8 C13 C12 -176.3(2) . . . . ? C9 C8 C13 N2 178.7(2) . . . . ? C7 C8 C13 N2 0.6(3) . . . . ? C12 C13 N2 C14 -49.0(3) . . . . ? C8 C13 N2 C14 134.3(2) . . . . ? C12 C13 N2 Zn 131.99(19) . . . . ? C8 C13 N2 Zn -44.7(2) . . . . ? N1 Zn N2 C14 -127.04(18) . . . . ? Cl2 Zn N2 C14 121.21(17) . . . . ? Cl1 Zn N2 C14 -6.78(19) . . . . ? N1 Zn N2 C13 51.90(14) . . . . ? Cl2 Zn N2 C13 -59.86(14) . . . . ? Cl1 Zn N2 C13 172.15(12) . . . . ? C13 N2 C14 N3 168.82(18) . . . . ? Zn N2 C14 N3 -12.3(3) . . . . ? C13 N2 C14 C15 -14.6(3) . . . . ? Zn N2 C14 C15 164.2(2) . . . . ? N2 C14 C15 C16 -179.8(3) . . . . ? N3 C14 C15 C16 -3.2(4) . . . . ? C14 C15 C16 C17 0.0(5) . . . . ? C15 C16 C17 C18 2.5(6) . . . . ? C16 C17 C18 N3 -1.5(5) . . . . ? C17 C18 N3 C14 -2.1(4) . . . . ? N2 C14 N3 C18 -178.7(2) . . . . ? C15 C14 N3 C18 4.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.668 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.049