# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Christer Aakeroy' 'John Desper' 'Naheed Haque' 'Izhar Hussain' _publ_contact_author_name 'Christer Aakeroy' _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Effective double-ended chelating agents; Crystal structures of N,N,N?,N?-tetraacetyl diamino derivatives and their chelates ; # Attachment 'all.cif' data_ih0501m(1) _database_code_depnum_ccdc_archive 'CCDC 769473' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl-a,a'-diamino-m-xylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O4' _chemical_formula_sum 'C16 H20 N2 O4' _chemical_formula_weight 304.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.3232(9) _cell_length_b 16.4424(11) _cell_length_c 13.4342(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.320(3) _cell_angle_gamma 90.00 _cell_volume 3102.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3982 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.60 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.094 _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 173(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 11242 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3589 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0700P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3589 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 C11 C 0.07317(9) 0.64306(7) 0.31275(9) 0.0255(3) Uani 1 1 d . . . C12 C 0.0000 0.68384(10) 0.2500 0.0251(4) Uani 1 2 d S . . H12 H 0.0000 0.7416 0.2500 0.030 Uiso 1 2 calc SR . . C15 C 0.0000 0.51702(10) 0.2500 0.0302(4) Uani 1 2 d S . . H15 H 0.0000 0.4592 0.2500 0.036 Uiso 1 2 calc SR . . C16 C 0.07263(9) 0.55849(7) 0.31247(9) 0.0285(3) Uani 1 1 d . . . H16 H 0.1221 0.5293 0.3552 0.034 Uiso 1 1 calc R . . C17 C 0.15379(9) 0.69162(7) 0.37387(10) 0.0293(3) Uani 1 1 d . . . H17A H 0.2041 0.6981 0.3334 0.035 Uiso 1 1 calc R . . H17B H 0.1300 0.7466 0.3859 0.035 Uiso 1 1 calc R . . N17 N 0.19639(7) 0.65525(6) 0.47234(8) 0.0263(3) Uani 1 1 d . . . C21 C 0.14397(10) 0.66776(8) 0.54945(10) 0.0328(3) Uani 1 1 d . . . O21 O 0.07122(8) 0.70683(7) 0.52864(8) 0.0487(3) Uani 1 1 d . . . C22 C 0.17727(12) 0.63426(10) 0.65332(11) 0.0459(4) Uani 1 1 d . . . H22A H 0.1871 0.5755 0.6491 0.069 Uiso 1 1 calc R . . H22B H 0.1293 0.6448 0.6946 0.069 Uiso 1 1 calc R . . H22C H 0.2373 0.6604 0.6847 0.069 Uiso 1 1 calc R . . C31 C 0.28229(10) 0.61272(8) 0.48463(11) 0.0329(3) Uani 1 1 d . . . O31 O 0.32071(9) 0.58662(8) 0.56590(9) 0.0624(4) Uani 1 1 d . . . C32 C 0.32575(11) 0.60188(9) 0.39322(13) 0.0438(4) Uani 1 1 d . . . H32A H 0.3498 0.6543 0.3743 0.066 Uiso 1 1 calc R . . H32B H 0.2775 0.5813 0.3368 0.066 Uiso 1 1 calc R . . H32C H 0.3784 0.5630 0.4086 0.066 Uiso 1 1 calc R . . C41 C 0.44037(9) 0.34275(7) 0.67234(9) 0.0255(3) Uani 1 1 d . . . C42 C 0.5000 0.30168(10) 0.7500 0.0249(4) Uani 1 2 d S . . H42 H 0.5000 0.2439 0.7500 0.030 Uiso 1 2 calc SR . . C45 C 0.5000 0.46865(10) 0.7500 0.0279(4) Uani 1 2 d S . . H45 H 0.5000 0.5264 0.7500 0.034 Uiso 1 2 calc SR . . C46 C 0.44033(9) 0.42725(8) 0.67340(9) 0.0274(3) Uani 1 1 d . . . H46 H 0.3993 0.4565 0.6215 0.033 Uiso 1 1 calc R . . C47 C 0.38052(9) 0.29429(7) 0.58800(9) 0.0285(3) Uani 1 1 d . . . H47A H 0.4207 0.2772 0.5396 0.034 Uiso 1 1 calc R . . H47B H 0.3575 0.2445 0.6170 0.034 Uiso 1 1 calc R . . N47 N 0.29838(7) 0.33996(6) 0.53280(8) 0.0261(2) Uani 1 1 d . . . C51 C 0.22175(9) 0.34626(7) 0.58379(9) 0.0283(3) Uani 1 1 d . . . O51 O 0.22476(7) 0.30531(6) 0.65945(7) 0.0394(3) Uani 1 1 d . . . C52 C 0.14126(10) 0.40322(8) 0.54797(11) 0.0367(3) Uani 1 1 d . . . H52A H 0.1664 0.4576 0.5392 0.055 Uiso 1 1 calc R . . H52B H 0.1001 0.4055 0.5982 0.055 Uiso 1 1 calc R . . H52C H 0.1043 0.3840 0.4830 0.055 Uiso 1 1 calc R . . C61 C 0.30044(10) 0.37604(8) 0.43924(10) 0.0300(3) Uani 1 1 d . . . O61 O 0.23143(8) 0.40932(6) 0.39009(7) 0.0424(3) Uani 1 1 d . . . C62 C 0.39145(11) 0.37102(10) 0.40077(11) 0.0435(4) Uani 1 1 d . . . H62A H 0.4028 0.3145 0.3831 0.065 Uiso 1 1 calc R . . H62B H 0.4442 0.3898 0.4536 0.065 Uiso 1 1 calc R . . H62C H 0.3869 0.4054 0.3404 0.065 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 C11 0.0255(7) 0.0300(6) 0.0213(6) -0.0003(5) 0.0057(5) -0.0019(5) C12 0.0285(10) 0.0254(8) 0.0220(8) 0.000 0.0067(7) 0.000 C15 0.0297(10) 0.0258(8) 0.0352(10) 0.000 0.0070(8) 0.000 C16 0.0256(7) 0.0308(6) 0.0285(7) 0.0038(5) 0.0039(5) 0.0025(5) C17 0.0287(7) 0.0315(6) 0.0257(6) 0.0027(5) 0.0002(5) -0.0021(5) N17 0.0239(6) 0.0314(5) 0.0232(5) 0.0000(4) 0.0036(4) 0.0001(4) C21 0.0309(8) 0.0374(7) 0.0310(7) -0.0081(5) 0.0087(6) -0.0069(6) O21 0.0351(6) 0.0650(7) 0.0479(7) -0.0120(5) 0.0124(5) 0.0108(5) C22 0.0577(11) 0.0548(9) 0.0278(7) -0.0010(6) 0.0145(7) -0.0071(8) C31 0.0270(7) 0.0323(7) 0.0386(8) 0.0001(6) 0.0043(6) 0.0020(5) O31 0.0556(8) 0.0791(8) 0.0499(7) 0.0188(6) 0.0040(6) 0.0321(6) C32 0.0316(8) 0.0482(8) 0.0559(10) -0.0084(7) 0.0193(7) -0.0012(6) C41 0.0190(6) 0.0303(6) 0.0277(7) -0.0012(5) 0.0056(5) -0.0002(5) C42 0.0222(9) 0.0241(8) 0.0289(9) 0.000 0.0063(7) 0.000 C45 0.0271(9) 0.0257(8) 0.0327(10) 0.000 0.0100(8) 0.000 C46 0.0235(7) 0.0305(6) 0.0286(7) 0.0028(5) 0.0062(5) 0.0044(5) C47 0.0240(7) 0.0319(6) 0.0279(6) -0.0015(5) 0.0012(5) 0.0035(5) N47 0.0211(6) 0.0329(5) 0.0237(5) -0.0009(4) 0.0031(4) 0.0015(4) C51 0.0264(7) 0.0338(6) 0.0250(6) -0.0048(5) 0.0055(5) -0.0029(5) O51 0.0405(6) 0.0511(6) 0.0290(5) 0.0057(4) 0.0129(5) 0.0025(5) C52 0.0297(8) 0.0428(8) 0.0400(8) -0.0016(6) 0.0124(6) 0.0058(6) C61 0.0320(8) 0.0324(6) 0.0259(7) -0.0019(5) 0.0064(6) -0.0022(6) O61 0.0451(6) 0.0528(6) 0.0287(5) 0.0080(4) 0.0052(5) 0.0113(5) C62 0.0396(9) 0.0547(9) 0.0411(9) 0.0028(7) 0.0197(7) -0.0045(7) _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 C11 C12 1.3826(14) . ? C11 C16 1.3905(17) . ? C11 C17 1.5077(17) . ? C12 C11 1.3826(14) 2 ? C12 H12 0.9500 . ? C15 C16 1.3816(15) . ? C15 C16 1.3816(15) 2 ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.4706(16) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N17 C31 1.3966(17) . ? N17 C21 1.4088(17) . ? C21 O21 1.2092(17) . ? C21 C22 1.489(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O31 1.2013(17) . ? C31 C32 1.492(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 C42 1.3872(14) . ? C41 C46 1.3894(17) . ? C41 C47 1.5074(17) . ? C42 C41 1.3872(14) 2_656 ? C42 H42 0.9500 . ? C45 C46 1.3811(15) . ? C45 C46 1.3811(15) 2_656 ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.4682(15) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? N47 C61 1.3953(16) . ? N47 C51 1.4070(16) . ? C51 O51 1.2129(15) . ? C51 C52 1.4901(18) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C61 O61 1.2067(16) . ? C61 C62 1.4959(19) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C12 C11 C16 118.70(11) . . ? C12 C11 C17 118.89(11) . . ? C16 C11 C17 122.30(11) . . ? C11 C12 C11 121.98(15) 2 . ? C11 C12 H12 119.0 2 . ? C11 C12 H12 119.0 . . ? C16 C15 C16 120.85(16) . 2 ? C16 C15 H15 119.6 . . ? C16 C15 H15 119.6 2 . ? C15 C16 C11 119.89(12) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? N17 C17 C11 114.37(10) . . ? N17 C17 H17A 108.7 . . ? C11 C17 H17A 108.7 . . ? N17 C17 H17B 108.7 . . ? C11 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C31 N17 C21 124.79(11) . . ? C31 N17 C17 120.68(11) . . ? C21 N17 C17 114.53(11) . . ? O21 C21 N17 117.84(12) . . ? O21 C21 C22 121.08(13) . . ? N17 C21 C22 121.08(12) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N17 121.48(13) . . ? O31 C31 C32 120.96(13) . . ? N17 C31 C32 117.55(12) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C42 C41 C46 118.72(11) . . ? C42 C41 C47 118.90(11) . . ? C46 C41 C47 122.34(11) . . ? C41 C42 C41 121.74(15) 2_656 . ? C41 C42 H42 119.1 2_656 . ? C41 C42 H42 119.1 . . ? C46 C45 C46 120.94(16) . 2_656 ? C46 C45 H45 119.5 . . ? C46 C45 H45 119.5 2_656 . ? C45 C46 C41 119.94(12) . . ? C45 C46 H46 120.0 . . ? C41 C46 H46 120.0 . . ? N47 C47 C41 112.98(10) . . ? N47 C47 H47A 109.0 . . ? C41 C47 H47A 109.0 . . ? N47 C47 H47B 109.0 . . ? C41 C47 H47B 109.0 . . ? H47A C47 H47B 107.8 . . ? C61 N47 C51 124.31(11) . . ? C61 N47 C47 121.06(11) . . ? C51 N47 C47 114.58(10) . . ? O51 C51 N47 117.67(12) . . ? O51 C51 C52 121.16(12) . . ? N47 C51 C52 121.14(11) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O61 C61 N47 121.73(12) . . ? O61 C61 C62 120.77(12) . . ? N47 C61 C62 117.49(12) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? 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 C16 C11 C12 C11 -0.10(8) . . . 2 ? C17 C11 C12 C11 176.02(12) . . . 2 ? C16 C15 C16 C11 -0.10(8) 2 . . . ? C12 C11 C16 C15 0.20(16) . . . . ? C17 C11 C16 C15 -175.78(10) . . . . ? C12 C11 C17 N17 148.12(10) . . . . ? C16 C11 C17 N17 -35.91(17) . . . . ? C11 C17 N17 C31 101.15(14) . . . . ? C11 C17 N17 C21 -79.20(14) . . . . ? C31 N17 C21 O21 178.95(12) . . . . ? C17 N17 C21 O21 -0.68(17) . . . . ? C31 N17 C21 C22 -0.80(19) . . . . ? C17 N17 C21 C22 179.57(12) . . . . ? C21 N17 C31 O31 -3.9(2) . . . . ? C17 N17 C31 O31 175.74(13) . . . . ? C21 N17 C31 C32 177.08(12) . . . . ? C17 N17 C31 C32 -3.31(17) . . . . ? C46 C41 C42 C41 -0.48(8) . . . 2_656 ? C47 C41 C42 C41 177.42(12) . . . 2_656 ? C46 C45 C46 C41 -0.49(8) 2_656 . . . ? C42 C41 C46 C45 0.96(16) . . . . ? C47 C41 C46 C45 -176.86(10) . . . . ? C42 C41 C47 N47 159.37(9) . . . . ? C46 C41 C47 N47 -22.81(17) . . . . ? C41 C47 N47 C61 100.33(13) . . . . ? C41 C47 N47 C51 -77.27(13) . . . . ? C61 N47 C51 O51 172.65(12) . . . . ? C47 N47 C51 O51 -9.83(16) . . . . ? C61 N47 C51 C52 -9.27(18) . . . . ? C47 N47 C51 C52 168.25(11) . . . . ? C51 N47 C61 O61 -7.40(19) . . . . ? C47 N47 C61 O61 175.24(11) . . . . ? C51 N47 C61 C62 173.49(12) . . . . ? C47 N47 C61 C62 -3.88(17) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.229 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.054 #END data_ih0516(2) _database_code_depnum_ccdc_archive 'CCDC 769474' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl-alpha,alpha'-diamino-p-xylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O4' _chemical_formula_sum 'C16 H20 N2 O4' _chemical_formula_weight 304.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.5627(5) _cell_length_b 13.5463(4) _cell_length_c 9.3888(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.444(2) _cell_angle_gamma 90.00 _cell_volume 1590.56(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3489 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 67.70 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.092 _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 150(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 5917 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1378 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0500P)^2^+1.3000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1378 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 C11 C 0.09153(14) 0.49331(11) 0.09837(17) 0.0284(4) Uani 1 1 d . . . C12 C 0.05807(13) 0.41355(12) 0.01181(17) 0.0313(4) Uani 1 1 d . . . H12 H 0.0979 0.3538 0.0190 0.038 Uiso 1 1 calc R . . C16 C 0.03240(13) 0.58025(11) 0.08467(17) 0.0293(4) Uani 1 1 d . . . H16 H 0.0542 0.6358 0.1419 0.035 Uiso 1 1 calc R . . C17 C 0.18673(14) 0.48716(12) 0.21016(19) 0.0351(4) Uani 1 1 d . . . H17A H 0.2205 0.5531 0.2213 0.042 Uiso 1 1 calc R . . H17B H 0.1613 0.4687 0.3032 0.042 Uiso 1 1 calc R . . N17 N 0.26769(11) 0.41488(11) 0.17336(16) 0.0360(4) Uani 1 1 d . . . C21 C 0.33604(15) 0.44853(15) 0.0735(2) 0.0443(5) Uani 1 1 d . . . O21 O 0.32676(11) 0.53355(11) 0.03188(17) 0.0538(4) Uani 1 1 d . . . C22 C 0.4156(2) 0.38109(18) 0.0164(4) 0.0765(8) Uani 1 1 d . . . H22A H 0.3786 0.3233 -0.0273 0.115 Uiso 1 1 calc R . . H22B H 0.4675 0.3597 0.0948 0.115 Uiso 1 1 calc R . . H22C H 0.4528 0.4159 -0.0557 0.115 Uiso 1 1 calc R . . C31 C 0.26790(16) 0.31881(14) 0.2291(2) 0.0454(5) Uani 1 1 d . . . O31 O 0.33267(16) 0.25773(13) 0.1999(2) 0.0810(6) Uani 1 1 d . . . C32 C 0.18408(18) 0.29379(15) 0.3263(2) 0.0507(5) Uani 1 1 d . . . H32A H 0.1973 0.3311 0.4156 0.076 Uiso 1 1 calc R . . H32B H 0.1866 0.2229 0.3472 0.076 Uiso 1 1 calc R . . H32C H 0.1134 0.3110 0.2796 0.076 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 C11 0.0342(9) 0.0266(8) 0.0241(9) 0.0015(6) 0.0018(6) 0.0026(7) C12 0.0387(9) 0.0238(8) 0.0309(9) 0.0018(6) 0.0004(7) 0.0072(7) C16 0.0379(9) 0.0241(8) 0.0256(9) -0.0016(6) 0.0017(7) 0.0011(7) C17 0.0391(10) 0.0309(9) 0.0335(10) -0.0044(7) -0.0054(7) 0.0086(7) N17 0.0351(8) 0.0351(8) 0.0358(9) -0.0056(6) -0.0069(6) 0.0087(6) C21 0.0355(10) 0.0449(11) 0.0508(12) -0.0113(9) -0.0044(8) -0.0037(8) O21 0.0491(9) 0.0503(9) 0.0614(10) 0.0016(7) 0.0021(7) -0.0070(7) C22 0.0652(16) 0.0544(14) 0.116(2) -0.0247(14) 0.0423(16) -0.0101(12) C31 0.0566(13) 0.0396(10) 0.0376(11) -0.0020(8) -0.0085(9) 0.0188(9) O31 0.1049(15) 0.0644(11) 0.0770(12) 0.0199(9) 0.0256(10) 0.0557(10) C32 0.0691(14) 0.0405(11) 0.0410(12) 0.0036(8) -0.0035(10) 0.0104(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 C11 C16 1.392(2) . ? C11 C12 1.393(2) . ? C11 C17 1.517(2) . ? C12 C16 1.387(2) 5_565 ? C12 H12 0.9500 . ? C16 C12 1.387(2) 5_565 ? C16 H16 0.9500 . ? C17 N17 1.476(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N17 C31 1.402(3) . ? N17 C21 1.406(3) . ? C21 O21 1.218(2) . ? C21 C22 1.490(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O31 1.210(2) . ? C31 C32 1.496(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 C16 C11 C12 118.27(15) . . ? C16 C11 C17 119.30(14) . . ? C12 C11 C17 122.39(14) . . ? C16 C12 C11 121.15(15) 5_565 . ? C16 C12 H12 119.4 5_565 . ? C11 C12 H12 119.4 . . ? C12 C16 C11 120.58(15) 5_565 . ? C12 C16 H16 119.7 5_565 . ? C11 C16 H16 119.7 . . ? N17 C17 C11 112.95(13) . . ? N17 C17 H17A 109.0 . . ? C11 C17 H17A 109.0 . . ? N17 C17 H17B 109.0 . . ? C11 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C31 N17 C21 124.73(16) . . ? C31 N17 C17 120.35(16) . . ? C21 N17 C17 114.77(15) . . ? O21 C21 N17 118.32(18) . . ? O21 C21 C22 120.8(2) . . ? N17 C21 C22 120.90(19) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N17 121.9(2) . . ? O31 C31 C32 120.69(19) . . ? N17 C31 C32 117.45(16) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C16 C11 C12 C16 -0.7(3) . . . 5_565 ? C17 C11 C12 C16 176.79(16) . . . 5_565 ? C12 C11 C16 C12 0.7(3) . . . 5_565 ? C17 C11 C16 C12 -176.88(15) . . . 5_565 ? C16 C11 C17 N17 -154.08(15) . . . . ? C12 C11 C17 N17 28.5(2) . . . . ? C11 C17 N17 C31 -96.17(19) . . . . ? C11 C17 N17 C21 79.57(19) . . . . ? C31 N17 C21 O21 178.97(16) . . . . ? C17 N17 C21 O21 3.4(2) . . . . ? C31 N17 C21 C22 0.8(3) . . . . ? C17 N17 C21 C22 -174.69(19) . . . . ? C21 N17 C31 O31 4.1(3) . . . . ? C17 N17 C31 O31 179.38(19) . . . . ? C21 N17 C31 C32 -175.59(16) . . . . ? C17 N17 C31 C32 -0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.218 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 #END data_nh0911m(3) _database_code_depnum_ccdc_archive 'CCDC 769475' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; NAP-12 tetraacetyl 1,5-naphthalenediamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 N2 O4' _chemical_formula_sum 'C18 H18 N2 O4' _chemical_formula_weight 326.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5245(6) _cell_length_b 10.3300(7) _cell_length_c 8.7471(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.108(4) _cell_angle_gamma 90.00 _cell_volume 826.82(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3351 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 32.21 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8965 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 33.23 _reflns_number_total 3132 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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^)+(0.0900P)^2^+0.0500P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3132 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C11 C 0.42721(9) 0.51686(10) 0.49869(11) 0.0369(2) Uani 1 1 d . . . C12 C 0.40610(10) 0.58788(11) 0.62973(12) 0.0397(2) Uani 1 1 d . . . N12 N 0.25920(9) 0.62378(10) 0.62842(11) 0.0439(2) Uani 1 1 d . . . C13 C 0.52068(12) 0.62377(13) 0.75496(14) 0.0484(3) Uani 1 1 d . . . H13 H 0.5042 0.6707 0.8391 0.058 Uiso 1 1 calc R . . C14 C 0.66361(12) 0.58932(13) 0.75588(14) 0.0523(3) Uani 1 1 d . . . H14 H 0.7415 0.6132 0.8416 0.063 Uiso 1 1 calc R . . C15 C 0.68995(10) 0.52141(12) 0.63288(14) 0.0457(3) Uani 1 1 d . . . H15 H 0.7854 0.5001 0.6353 0.055 Uiso 1 1 calc R . . C21 C 0.17707(13) 0.53882(14) 0.69586(15) 0.0538(3) Uani 1 1 d . . . O21 O 0.05070(11) 0.55850(13) 0.68843(15) 0.0819(4) Uani 1 1 d . . . C22 C 0.2557(2) 0.42322(15) 0.7775(2) 0.0763(5) Uani 1 1 d . . . H22A H 0.1898 0.3707 0.8164 0.114 Uiso 1 1 calc R . . H22B H 0.3357 0.4502 0.8651 0.114 Uiso 1 1 calc R . . H22C H 0.2924 0.3739 0.7039 0.114 Uiso 1 1 calc R . . C31 C 0.21192(13) 0.74357(14) 0.55650(15) 0.0534(3) Uani 1 1 d . . . O31 O 0.29291(12) 0.80231(11) 0.49631(14) 0.0763(4) Uani 1 1 d . . . C32 C 0.06641(17) 0.79619(19) 0.5569(2) 0.0795(5) Uani 1 1 d . . . H32A H 0.0529 0.8796 0.5066 0.119 Uiso 1 1 calc R . . H32B H 0.0615 0.8044 0.6646 0.119 Uiso 1 1 calc R . . H32C H -0.0089 0.7384 0.4997 0.119 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 C11 0.0232(4) 0.0463(5) 0.0429(5) 0.0019(4) 0.0120(3) -0.0002(3) C12 0.0258(4) 0.0494(6) 0.0471(5) 0.0010(4) 0.0153(4) 0.0013(4) N12 0.0279(4) 0.0583(6) 0.0500(5) -0.0018(4) 0.0179(3) 0.0025(4) C13 0.0357(5) 0.0617(7) 0.0492(6) -0.0088(5) 0.0142(4) -0.0003(5) C14 0.0292(5) 0.0719(8) 0.0522(6) -0.0120(5) 0.0056(4) -0.0026(5) C15 0.0227(4) 0.0621(7) 0.0519(6) -0.0024(5) 0.0097(4) 0.0006(4) C21 0.0365(5) 0.0744(8) 0.0563(6) -0.0090(6) 0.0229(5) -0.0123(5) O21 0.0355(5) 0.1220(10) 0.0964(8) -0.0008(7) 0.0316(5) -0.0121(5) C22 0.0746(10) 0.0687(9) 0.0998(12) 0.0117(8) 0.0480(9) -0.0097(8) C31 0.0427(6) 0.0659(8) 0.0550(6) 0.0007(5) 0.0190(5) 0.0135(5) O31 0.0686(7) 0.0762(7) 0.0967(8) 0.0290(6) 0.0439(6) 0.0211(5) C32 0.0511(8) 0.0972(12) 0.0948(11) 0.0057(9) 0.0276(7) 0.0314(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 C11 C15 1.4189(14) 3_666 ? C11 C12 1.4215(14) . ? C11 C11 1.4236(17) 3_666 ? C12 C13 1.3656(15) . ? C12 N12 1.4444(12) . ? N12 C31 1.4045(17) . ? N12 C21 1.4094(15) . ? C13 C14 1.4049(15) . ? C13 H13 0.9300 . ? C14 C15 1.3646(16) . ? C14 H14 0.9300 . ? C15 C11 1.4189(14) 3_666 ? C15 H15 0.9300 . ? C21 O21 1.2045(15) . ? C21 C22 1.483(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C31 O31 1.2107(16) . ? C31 C32 1.4895(17) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? 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 C15 C11 C12 122.85(8) 3_666 . ? C15 C11 C11 119.22(11) 3_666 3_666 ? C12 C11 C11 117.92(11) . 3_666 ? C13 C12 C11 121.77(9) . . ? C13 C12 N12 119.57(9) . . ? C11 C12 N12 118.65(8) . . ? C31 N12 C21 126.15(10) . . ? C31 N12 C12 114.79(9) . . ? C21 N12 C12 119.06(9) . . ? C12 C13 C14 119.56(10) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 121.03(10) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C11 120.49(9) . 3_666 ? C14 C15 H15 119.8 . . ? C11 C15 H15 119.8 3_666 . ? O21 C21 N12 122.33(14) . . ? O21 C21 C22 121.68(13) . . ? N12 C21 C22 115.99(10) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N12 118.20(10) . . ? O31 C31 C32 121.57(13) . . ? N12 C31 C32 120.23(12) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C15 C11 C12 C13 -179.92(11) 3_666 . . . ? C11 C11 C12 C13 0.20(19) 3_666 . . . ? C15 C11 C12 N12 -0.59(16) 3_666 . . . ? C11 C11 C12 N12 179.52(11) 3_666 . . . ? C13 C12 N12 C31 89.91(13) . . . . ? C11 C12 N12 C31 -89.43(13) . . . . ? C13 C12 N12 C21 -90.48(14) . . . . ? C11 C12 N12 C21 90.18(13) . . . . ? C11 C12 C13 C14 -0.41(19) . . . . ? N12 C12 C13 C14 -179.72(10) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C13 C14 C15 C11 -0.46(19) . . . 3_666 ? C31 N12 C21 O21 5.0(2) . . . . ? C12 N12 C21 O21 -174.51(12) . . . . ? C31 N12 C21 C22 -174.77(13) . . . . ? C12 N12 C21 C22 5.67(17) . . . . ? C21 N12 C31 O31 -176.10(12) . . . . ? C12 N12 C31 O31 3.47(17) . . . . ? C21 N12 C31 C32 4.5(2) . . . . ? C12 N12 C31 C32 -175.88(12) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 33.23 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.300 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.041 #END data_ih0509m(4) _database_code_depnum_ccdc_archive 'CCDC 769476' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl 1,4-cyclohexanediamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 N2 O4' _chemical_formula_sum 'C14 H22 N2 O4' _chemical_formula_weight 282.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3457(13) _cell_length_b 5.8212(6) _cell_length_c 10.0737(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.176(7) _cell_angle_gamma 90.00 _cell_volume 691.68(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1423 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.60 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.099 _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 173(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 4787 _diffrn_reflns_av_R_equivalents 0.1136 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1605 _reflns_number_gt 1361 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1605 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.1830 _refine_ls_wR_factor_gt 0.1739 _refine_ls_goodness_of_fit_ref 1.331 _refine_ls_restrained_S_all 1.331 _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 C11 C 0.37765(11) 0.5039(2) 0.44362(13) 0.0184(4) Uani 1 1 d . . . H11 H 0.3783 0.6023 0.3625 0.022 Uiso 1 1 calc R . . N11 N 0.25611(10) 0.4610(2) 0.43046(11) 0.0191(3) Uani 1 1 d . . . C12 C 0.44439(12) 0.2886(2) 0.43218(14) 0.0206(4) Uani 1 1 d . . . H12A H 0.4044 0.2028 0.3470 0.025 Uiso 1 1 calc R . . H12B H 0.4507 0.1877 0.5132 0.025 Uiso 1 1 calc R . . C16 C 0.43739(12) 0.6433(3) 0.57294(14) 0.0208(4) Uani 1 1 d . . . H16A H 0.4436 0.5507 0.6573 0.025 Uiso 1 1 calc R . . H16B H 0.3927 0.7829 0.5772 0.025 Uiso 1 1 calc R . . C21 C 0.17293(12) 0.6139(2) 0.35420(13) 0.0218(4) Uani 1 1 d . . . O21 O 0.07827(9) 0.6137(2) 0.36504(12) 0.0332(4) Uani 1 1 d . . . C22 C 0.20528(13) 0.7824(3) 0.25929(15) 0.0280(4) Uani 1 1 d . . . H22A H 0.2406 0.7002 0.1979 0.042 Uiso 1 1 calc R . . H22B H 0.2590 0.8945 0.3149 0.042 Uiso 1 1 calc R . . H22C H 0.1373 0.8624 0.2032 0.042 Uiso 1 1 calc R . . C31 C 0.22790(12) 0.2845(3) 0.50967(13) 0.0205(4) Uani 1 1 d . . . O31 O 0.30221(9) 0.1994(2) 0.60468(10) 0.0282(4) Uani 1 1 d . . . C32 C 0.10962(13) 0.1927(3) 0.47195(16) 0.0284(4) Uani 1 1 d . . . H32A H 0.0632 0.2907 0.5126 0.043 Uiso 1 1 calc R . . H32B H 0.1107 0.0360 0.5079 0.043 Uiso 1 1 calc R . . H32C H 0.0774 0.1911 0.3706 0.043 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 C11 0.0115(7) 0.0210(7) 0.0225(6) 0.0008(5) 0.0047(5) -0.0009(5) N11 0.0135(6) 0.0215(6) 0.0220(6) 0.0014(4) 0.0050(4) -0.0001(5) C12 0.0156(7) 0.0203(7) 0.0253(6) -0.0040(5) 0.0052(5) -0.0017(5) C16 0.0164(7) 0.0212(7) 0.0259(6) -0.0034(5) 0.0080(5) -0.0003(5) C21 0.0180(7) 0.0224(8) 0.0235(6) -0.0013(5) 0.0040(5) 0.0019(6) O21 0.0188(6) 0.0362(7) 0.0466(7) 0.0094(5) 0.0127(5) 0.0061(5) C22 0.0218(8) 0.0287(8) 0.0322(7) 0.0078(6) 0.0058(6) 0.0040(6) C31 0.0195(7) 0.0219(8) 0.0217(6) -0.0019(5) 0.0086(5) -0.0004(5) O31 0.0226(6) 0.0326(7) 0.0279(6) 0.0088(4) 0.0049(4) -0.0007(4) C32 0.0199(8) 0.0250(8) 0.0407(8) 0.0009(6) 0.0096(6) -0.0047(6) _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 C11 N11 1.4879(17) . ? C11 C12 1.523(2) . ? C11 C16 1.5270(18) . ? C11 H11 1.0000 . ? N11 C21 1.4037(18) . ? N11 C31 1.4066(19) . ? C12 C16 1.5278(19) 3_666 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C16 C12 1.5278(19) 3_666 ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 O21 1.2053(19) . ? C21 C22 1.5041(19) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O31 1.2183(18) . ? C31 C32 1.495(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 N11 C11 C12 114.15(11) . . ? N11 C11 C16 112.67(11) . . ? C12 C11 C16 111.47(11) . . ? N11 C11 H11 105.9 . . ? C12 C11 H11 105.9 . . ? C16 C11 H11 105.9 . . ? C21 N11 C31 120.66(12) . . ? C21 N11 C11 119.86(11) . . ? C31 N11 C11 118.96(11) . . ? C11 C12 C16 109.43(11) . 3_666 ? C11 C12 H12A 109.8 . . ? C16 C12 H12A 109.8 3_666 . ? C11 C12 H12B 109.8 . . ? C16 C12 H12B 109.8 3_666 . ? H12A C12 H12B 108.2 . . ? C11 C16 C12 109.55(11) . 3_666 ? C11 C16 H16A 109.8 . . ? C12 C16 H16A 109.8 3_666 . ? C11 C16 H16B 109.8 . . ? C12 C16 H16B 109.8 3_666 . ? H16A C16 H16B 108.2 . . ? O21 C21 N11 121.46(14) . . ? O21 C21 C22 120.32(13) . . ? N11 C21 C22 118.21(13) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N11 119.17(14) . . ? O31 C31 C32 120.46(14) . . ? N11 C31 C32 120.26(12) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C12 C11 N11 C21 -139.45(13) . . . . ? C16 C11 N11 C21 92.09(14) . . . . ? C12 C11 N11 C31 48.76(15) . . . . ? C16 C11 N11 C31 -79.70(16) . . . . ? N11 C11 C12 C16 172.26(10) . . . 3_666 ? C16 C11 C12 C16 -58.67(16) . . . 3_666 ? N11 C11 C16 C12 -171.42(11) . . . 3_666 ? C12 C11 C16 C12 58.74(16) . . . 3_666 ? C31 N11 C21 O21 7.6(2) . . . . ? C11 N11 C21 O21 -164.09(13) . . . . ? C31 N11 C21 C22 -173.40(12) . . . . ? C11 N11 C21 C22 14.95(18) . . . . ? C21 N11 C31 O31 -158.41(13) . . . . ? C11 N11 C31 O31 13.31(19) . . . . ? C21 N11 C31 C32 25.38(19) . . . . ? C11 N11 C31 C32 -162.90(12) . . . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.317 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.101 #END data_ih0503m(5) _database_code_depnum_ccdc_archive 'CCDC 769477' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl ethylenediamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N2 O4' _chemical_formula_sum 'C10 H16 N2 O4' _chemical_formula_weight 228.25 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9150(4) _cell_length_b 10.1956(7) _cell_length_c 9.1495(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.388(5) _cell_angle_gamma 90.00 _cell_volume 548.35(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2490 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 28.25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.107 _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 173(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_reflns_number 3859 _diffrn_reflns_av_R_equivalents 0.1094 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1258 _reflns_number_gt 1099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0950P)^2^+0.1000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.10(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1258 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 C1 C 0.4181(2) 0.47914(12) 0.43407(12) 0.0195(4) Uani 1 1 d . . . H1A H 0.2670 0.5190 0.4411 0.023 Uiso 1 1 calc R . . H1B H 0.4744 0.5112 0.3426 0.023 Uiso 1 1 calc R . . N1 N 0.39578(18) 0.33560(11) 0.42801(10) 0.0193(3) Uani 1 1 d . A . C2 C 0.2238(2) 0.28174(13) 0.50459(13) 0.0207(4) Uani 1 1 d . . . C3A C 0.1546(2) 0.14134(13) 0.47971(16) 0.0275(4) Uani 0.74(2) 1 d P A 1 H3A H 0.2468 0.0854 0.5502 0.041 Uiso 0.74(2) 1 calc PR A 1 H3B H 0.1782 0.1156 0.3793 0.041 Uiso 0.74(2) 1 calc PR A 1 H3C H -0.0065 0.1313 0.4934 0.041 Uiso 0.74(2) 1 calc PR A 1 C3B C 0.1546(2) 0.14134(13) 0.47971(16) 0.0275(4) Uani 0.26(2) 1 d P A 2 H3D H 0.2881 0.0847 0.5003 0.041 Uiso 0.26(2) 1 calc PR A 2 H3E H 0.0897 0.1296 0.3772 0.041 Uiso 0.26(2) 1 calc PR A 2 H3F H 0.0407 0.1180 0.5453 0.041 Uiso 0.26(2) 1 calc PR A 2 O2 O 0.12696(18) 0.35284(10) 0.58359(11) 0.0292(4) Uani 1 1 d . A . C4 C 0.5533(2) 0.25979(13) 0.36187(13) 0.0207(4) Uani 1 1 d . . . O4 O 0.56746(17) 0.14228(9) 0.38101(11) 0.0277(4) Uani 1 1 d . A . C5 C 0.7058(3) 0.33027(15) 0.26754(14) 0.0271(4) Uani 1 1 d . A . H5A H 0.8070 0.3893 0.3288 0.041 Uiso 1 1 calc R . . H5B H 0.6131 0.3814 0.1924 0.041 Uiso 1 1 calc R . . H5C H 0.7969 0.2662 0.2197 0.041 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 C1 0.0233(7) 0.0132(6) 0.0221(6) 0.0008(4) 0.0032(5) 0.0003(4) N1 0.0221(6) 0.0141(6) 0.0222(6) -0.0003(4) 0.0049(5) -0.0006(4) C2 0.0205(7) 0.0188(6) 0.0226(6) 0.0011(5) 0.0022(5) -0.0016(5) C3A 0.0257(8) 0.0185(7) 0.0386(8) 0.0002(5) 0.0047(6) -0.0050(5) C3B 0.0257(8) 0.0185(7) 0.0386(8) 0.0002(5) 0.0047(6) -0.0050(5) O2 0.0307(6) 0.0254(6) 0.0338(6) -0.0037(4) 0.0134(5) -0.0018(4) C4 0.0225(7) 0.0202(7) 0.0190(6) -0.0030(4) 0.0006(5) 0.0012(5) O4 0.0317(6) 0.0180(6) 0.0339(6) -0.0024(4) 0.0061(4) 0.0031(4) C5 0.0281(8) 0.0300(8) 0.0242(7) -0.0005(5) 0.0079(5) 0.0003(6) _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 N1 1.4699(16) . ? C1 C1 1.522(2) 3_666 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? N1 C4 1.3989(16) . ? N1 C2 1.4093(15) . ? C2 O2 1.2116(16) . ? C2 C3A 1.4992(17) . ? C3A H3A 0.9800 . ? C3A H3B 0.9800 . ? C3A H3C 0.9800 . ? C4 O4 1.2123(17) . ? C4 C5 1.4993(18) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? 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 C1 C1 110.78(12) . 3_666 ? N1 C1 H1A 109.5 . . ? C1 C1 H1A 109.5 3_666 . ? N1 C1 H1B 109.5 . . ? C1 C1 H1B 109.5 3_666 . ? H1A C1 H1B 108.1 . . ? C4 N1 C2 123.52(12) . . ? C4 N1 C1 120.34(10) . . ? C2 N1 C1 115.84(10) . . ? O2 C2 N1 118.61(12) . . ? O2 C2 C3A 121.51(12) . . ? N1 C2 C3A 119.77(11) . . ? C2 C3A H3A 109.5 . . ? C2 C3A H3B 109.5 . . ? H3A C3A H3B 109.5 . . ? C2 C3A H3C 109.5 . . ? H3A C3A H3C 109.5 . . ? H3B C3A H3C 109.5 . . ? O4 C4 N1 121.48(11) . . ? O4 C4 C5 121.36(12) . . ? N1 C4 C5 117.16(12) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 C1 N1 C4 -84.46(14) 3_666 . . . ? C1 C1 N1 C2 89.42(15) 3_666 . . . ? C4 N1 C2 O2 164.69(12) . . . . ? C1 N1 C2 O2 -8.97(17) . . . . ? C4 N1 C2 C3A -19.15(17) . . . . ? C1 N1 C2 C3A 167.18(11) . . . . ? C2 N1 C4 O4 -8.62(18) . . . . ? C1 N1 C4 O4 164.78(11) . . . . ? C2 N1 C4 C5 172.05(11) . . . . ? C1 N1 C4 C5 -14.56(16) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.516 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.107 #END data_ih0538m(6a) _database_code_depnum_ccdc_archive 'CCDC 769478' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl 1,4-diaminobutane Cu(OH2)2 (ClO4)2 (H2O)2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; Cu (H2 O)2 (C12 H20 N2 O4) (Cl O4)2 ; _chemical_formula_sum 'C12 H24 Cl2 Cu N2 O14' _chemical_formula_weight 554.77 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' Cu Cu 0.3201 1.2651 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3645(4) _cell_length_b 12.3273(7) _cell_length_c 11.7535(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.600(3) _cell_angle_gamma 90.00 _cell_volume 1048.83(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6561 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.25 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 1.370 _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 173(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 13350 _diffrn_reflns_av_R_equivalents 0.1405 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2509 _reflns_number_gt 2075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0600P)^2^+0.7000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2509 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1106 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.01805(18) Uani 1 2 d S . . Cl1 Cl 0.49962(9) 0.70245(5) 0.84907(5) 0.0228(2) Uani 1 1 d . . . O11 O 0.3453(3) 0.7479(2) 0.7722(2) 0.0436(6) Uani 1 1 d . . . O12 O 0.6492(3) 0.69087(19) 0.7865(2) 0.0387(5) Uani 1 1 d . . . O13 O 0.5547(4) 0.7734(2) 0.9450(2) 0.0447(6) Uani 1 1 d . . . O14 O 0.4509(3) 0.59927(18) 0.8885(2) 0.0389(5) Uani 1 1 d . . . O1 O 0.4260(3) 0.67449(17) 0.53999(17) 0.0322(5) Uani 1 1 d . . . H1A H 0.4300 0.6813 0.6115 0.039 Uiso 1 1 calc R . . H1B H 0.3124 0.6846 0.5169 0.039 Uiso 1 1 d R . . C11 C 0.9251(3) 0.4305(2) 0.85350(19) 0.0173(5) Uani 1 1 d . . . H11A H 1.0501 0.4223 0.8347 0.021 Uiso 1 1 calc R . . H11B H 0.8911 0.3605 0.8851 0.021 Uiso 1 1 calc R . . N11 N 0.7916(3) 0.45487(16) 0.74499(16) 0.0155(4) Uani 1 1 d . . . C12 C 0.9315(4) 0.5171(2) 0.9457(2) 0.0186(5) Uani 1 1 d . . . H12A H 0.8071 0.5269 0.9647 0.022 Uiso 1 1 calc R . . H12B H 0.9707 0.5871 0.9165 0.022 Uiso 1 1 calc R . . C21 C 0.6088(3) 0.42332(19) 0.7366(2) 0.0174(5) Uani 1 1 d . . . O21 O 0.4870(2) 0.44504(16) 0.65349(14) 0.0214(4) Uani 1 1 d . . . C22 C 0.5570(4) 0.3585(2) 0.8331(2) 0.0253(6) Uani 1 1 d . . . H22A H 0.4232 0.3465 0.8181 0.038 Uiso 1 1 calc R . . H22B H 0.5929 0.3981 0.9061 0.038 Uiso 1 1 calc R . . H22C H 0.6209 0.2885 0.8385 0.038 Uiso 1 1 calc R . . C23 C 0.8540(3) 0.51068(19) 0.6569(2) 0.0166(5) Uani 1 1 d . . . O23 O 0.7557(2) 0.53241(16) 0.56342(15) 0.0206(4) Uani 1 1 d . . . C24 C 1.0518(3) 0.5439(2) 0.6745(2) 0.0254(6) Uani 1 1 d . . . H24A H 1.0697 0.5945 0.6132 0.038 Uiso 1 1 calc R . . H24B H 1.1292 0.4796 0.6719 0.038 Uiso 1 1 calc R . . H24C H 1.0865 0.5794 0.7500 0.038 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 Cu1 0.0137(2) 0.0283(3) 0.0101(2) 0.00366(15) -0.00329(15) -0.00300(15) Cl1 0.0270(3) 0.0205(3) 0.0190(3) -0.0001(2) -0.0006(2) 0.0008(2) O11 0.0306(12) 0.0465(14) 0.0491(14) 0.0162(11) -0.0054(10) 0.0053(10) O12 0.0428(13) 0.0396(13) 0.0376(12) 0.0043(9) 0.0182(10) 0.0097(10) O13 0.0499(14) 0.0492(14) 0.0348(12) -0.0219(11) 0.0073(10) -0.0168(11) O14 0.0547(14) 0.0268(11) 0.0338(12) 0.0072(9) 0.0050(10) -0.0043(10) O1 0.0375(11) 0.0334(11) 0.0233(10) -0.0025(8) -0.0013(8) -0.0002(9) C11 0.0175(11) 0.0210(12) 0.0104(10) 0.0000(8) -0.0051(8) 0.0022(9) N11 0.0153(9) 0.0185(10) 0.0106(9) -0.0009(7) -0.0028(7) -0.0009(8) C12 0.0193(12) 0.0230(12) 0.0104(11) -0.0022(9) -0.0057(9) 0.0033(9) C21 0.0176(11) 0.0202(12) 0.0131(11) -0.0011(9) -0.0001(8) -0.0026(9) O21 0.0157(8) 0.0341(11) 0.0127(8) 0.0018(7) -0.0021(6) -0.0040(7) C22 0.0248(13) 0.0310(14) 0.0187(12) 0.0058(10) 0.0004(9) -0.0074(11) C23 0.0169(11) 0.0176(11) 0.0144(11) -0.0015(8) 0.0007(9) -0.0011(8) O23 0.0164(8) 0.0311(10) 0.0125(8) 0.0053(7) -0.0023(6) -0.0039(7) C24 0.0175(12) 0.0369(15) 0.0198(12) 0.0052(11) -0.0018(9) -0.0074(11) _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 Cu1 O23 1.9354(17) . ? Cu1 O23 1.9355(17) 3_666 ? Cu1 O21 1.9457(17) 3_666 ? Cu1 O21 1.9458(17) . ? Cu1 O1 2.289(2) 3_666 ? Cu1 O1 2.289(2) . ? Cl1 O14 1.422(2) . ? Cl1 O13 1.426(2) . ? Cl1 O11 1.430(2) . ? Cl1 O12 1.440(2) . ? O1 H1A 0.8400 . ? O1 H1B 0.8399 . ? C11 N11 1.491(3) . ? C11 C12 1.516(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C21 1.388(3) . ? N11 C23 1.389(3) . ? C12 C12 1.534(5) 3_767 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C21 O21 1.228(3) . ? C21 C22 1.493(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O23 1.229(3) . ? C23 C24 1.490(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 O23 Cu1 O23 180.0 . 3_666 ? O23 Cu1 O21 94.30(7) . 3_666 ? O23 Cu1 O21 85.70(7) 3_666 3_666 ? O23 Cu1 O21 85.70(7) . . ? O23 Cu1 O21 94.30(7) 3_666 . ? O21 Cu1 O21 180.00(11) 3_666 . ? O23 Cu1 O1 91.22(8) . 3_666 ? O23 Cu1 O1 88.78(8) 3_666 3_666 ? O21 Cu1 O1 94.74(8) 3_666 3_666 ? O21 Cu1 O1 85.26(8) . 3_666 ? O23 Cu1 O1 88.78(8) . . ? O23 Cu1 O1 91.22(8) 3_666 . ? O21 Cu1 O1 85.26(8) 3_666 . ? O21 Cu1 O1 94.74(8) . . ? O1 Cu1 O1 180.00(11) 3_666 . ? O14 Cl1 O13 110.07(15) . . ? O14 Cl1 O11 109.74(15) . . ? O13 Cl1 O11 109.68(16) . . ? O14 Cl1 O12 109.89(14) . . ? O13 Cl1 O12 109.39(15) . . ? O11 Cl1 O12 108.03(15) . . ? Cu1 O1 H1A 109.5 . . ? Cu1 O1 H1B 109.5 . . ? H1A O1 H1B 99.2 . . ? N11 C11 C12 113.46(19) . . ? N11 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N11 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C21 N11 C23 122.4(2) . . ? C21 N11 C11 118.89(19) . . ? C23 N11 C11 118.7(2) . . ? C11 C12 C12 109.3(2) . 3_767 ? C11 C12 H12A 109.8 . . ? C12 C12 H12A 109.8 3_767 . ? C11 C12 H12B 109.8 . . ? C12 C12 H12B 109.8 3_767 . ? H12A C12 H12B 108.3 . . ? O21 C21 N11 123.5(2) . . ? O21 C21 C22 118.0(2) . . ? N11 C21 C22 118.4(2) . . ? C21 O21 Cu1 131.33(16) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O23 C23 N11 123.6(2) . . ? O23 C23 C24 117.6(2) . . ? N11 C23 C24 118.8(2) . . ? C23 O23 Cu1 132.10(17) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 C12 C11 N11 C21 -87.0(3) . . . . ? C12 C11 N11 C23 91.5(3) . . . . ? N11 C11 C12 C12 178.5(3) . . . 3_767 ? C23 N11 C21 O21 -2.6(4) . . . . ? C11 N11 C21 O21 175.8(2) . . . . ? C23 N11 C21 C22 176.8(2) . . . . ? C11 N11 C21 C22 -4.8(3) . . . . ? N11 C21 O21 Cu1 13.4(4) . . . . ? C22 C21 O21 Cu1 -166.04(19) . . . . ? O23 Cu1 O21 C21 -13.4(2) . . . . ? O23 Cu1 O21 C21 166.6(2) 3_666 . . . ? O1 Cu1 O21 C21 78.1(2) 3_666 . . . ? O1 Cu1 O21 C21 -101.9(2) . . . . ? C21 N11 C23 O23 -3.2(4) . . . . ? C11 N11 C23 O23 178.3(2) . . . . ? C21 N11 C23 C24 178.5(2) . . . . ? C11 N11 C23 C24 0.0(3) . . . . ? N11 C23 O23 Cu1 -1.7(4) . . . . ? C24 C23 O23 Cu1 176.61(18) . . . . ? O21 Cu1 O23 C23 -172.5(2) 3_666 . . . ? O21 Cu1 O23 C23 7.5(2) . . . . ? O1 Cu1 O23 C23 -77.6(2) 3_666 . . . ? O1 Cu1 O23 C23 102.4(2) . . . . ? 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 O1 H1A O11 0.84 2.25 3.036(3) 155.8 . O1 H1A O12 0.84 2.37 3.063(3) 140.0 . O1 H1B O13 0.84 2.00 2.830(3) 170.8 4_575 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.711 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.129 #END data_ih0535m(6) _database_code_depnum_ccdc_archive 'CCDC 769479' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetraacetyl 1,4-butanediamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 N2 O4' _chemical_formula_sum 'C12 H20 N2 O4' _chemical_formula_weight 256.30 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.7246(15) _cell_length_b 11.3474(11) _cell_length_c 7.8352(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.917(5) _cell_angle_gamma 90.00 _cell_volume 1309.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2027 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.05 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.098 _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 173(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 4813 _diffrn_reflns_av_R_equivalents 0.1257 _diffrn_reflns_av_sigmaI/netI 0.0931 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.21 _reflns_number_total 1536 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1536 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1776 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 C11 C 0.23015(10) 0.26804(12) 0.25821(19) 0.0249(4) Uani 1 1 d . . . H11A H 0.2530 0.3500 0.2519 0.030 Uiso 1 1 calc R . . H11B H 0.2793 0.2152 0.2201 0.030 Uiso 1 1 calc R . . N11 N 0.15192(9) 0.25558(10) 0.14095(16) 0.0240(4) Uani 1 1 d . . . C12 C 0.20866(10) 0.23966(12) 0.44227(19) 0.0243(4) Uani 1 1 d . . . H12A H 0.1894 0.1563 0.4510 0.036 Uiso 1 1 calc R . . H12B H 0.1579 0.2899 0.4802 0.036 Uiso 1 1 calc R . . C21 C 0.13854(11) 0.14371(13) 0.0699(2) 0.0282(4) Uani 1 1 d . . . O21 O 0.18753(9) 0.06345(10) 0.11748(17) 0.0422(4) Uani 1 1 d . . . C22 C 0.06921(12) 0.12449(16) -0.0675(2) 0.0383(5) Uani 1 1 d . . . H22A H 0.0818 0.0502 -0.1263 0.057 Uiso 1 1 calc R . . H22B H 0.0714 0.1897 -0.1494 0.057 Uiso 1 1 calc R . . H22C H 0.0087 0.1210 -0.0174 0.057 Uiso 1 1 calc R . . C31 C 0.09227(11) 0.35036(13) 0.1121(2) 0.0278(4) Uani 1 1 d . . . O31 O 0.02088(9) 0.33751(10) 0.0386(2) 0.0443(4) Uani 1 1 d . . . C32 C 0.12154(12) 0.46852(13) 0.1784(2) 0.0338(5) Uani 1 1 d . . . H32A H 0.0762 0.5279 0.1457 0.051 Uiso 1 1 calc R . . H32B H 0.1803 0.4895 0.1298 0.051 Uiso 1 1 calc R . . H32C H 0.1273 0.4654 0.3031 0.051 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 C11 0.0234(9) 0.0300(7) 0.0211(8) 0.0018(6) -0.0042(6) 0.0017(6) N11 0.0254(8) 0.0270(7) 0.0194(7) 0.0017(5) -0.0049(5) 0.0006(5) C12 0.0239(9) 0.0278(7) 0.0211(8) 0.0020(5) -0.0040(7) 0.0000(6) C21 0.0315(9) 0.0289(8) 0.0241(8) 0.0005(6) -0.0005(7) -0.0009(6) O21 0.0539(9) 0.0296(6) 0.0427(8) -0.0015(5) -0.0108(6) 0.0086(5) C22 0.0354(10) 0.0410(9) 0.0381(11) -0.0089(8) -0.0074(8) -0.0050(7) C31 0.0278(9) 0.0303(8) 0.0250(8) 0.0045(6) -0.0052(7) 0.0026(6) O31 0.0368(9) 0.0398(7) 0.0556(9) -0.0034(6) -0.0227(6) 0.0052(5) C32 0.0380(10) 0.0281(8) 0.0353(10) 0.0014(7) -0.0065(7) 0.0031(6) _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 C11 N11 1.4687(18) . ? C11 C12 1.516(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C21 1.3989(19) . ? N11 C31 1.4046(18) . ? C12 C12 1.523(3) 7_556 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C21 O21 1.217(2) . ? C21 C22 1.488(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O31 1.199(2) . ? C31 C32 1.499(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 N11 C11 C12 113.65(12) . . ? N11 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N11 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C21 N11 C31 123.16(14) . . ? C21 N11 C11 116.13(11) . . ? C31 N11 C11 120.61(12) . . ? C11 C12 C12 110.80(15) . 7_556 ? C11 C12 H12A 109.5 . . ? C12 C12 H12A 109.5 7_556 . ? C11 C12 H12B 109.5 . . ? C12 C12 H12B 109.5 7_556 . ? H12A C12 H12B 108.1 . . ? O21 C21 N11 118.57(15) . . ? O21 C21 C22 120.57(14) . . ? N11 C21 C22 120.78(13) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N11 121.69(14) . . ? O31 C31 C32 121.34(14) . . ? N11 C31 C32 116.97(14) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C12 C11 N11 C21 -88.53(16) . . . . ? C12 C11 N11 C31 87.98(16) . . . . ? N11 C11 C12 C12 -177.15(13) . . . 7_556 ? C31 N11 C21 O21 -171.48(15) . . . . ? C11 N11 C21 O21 4.9(2) . . . . ? C31 N11 C21 C22 11.7(2) . . . . ? C11 N11 C21 C22 -171.86(14) . . . . ? C21 N11 C31 O31 7.9(2) . . . . ? C11 N11 C31 O31 -168.31(16) . . . . ? C21 N11 C31 C32 -172.47(14) . . . . ? C11 N11 C31 C32 11.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.385 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.085 #END data_ih0517(7) _database_code_depnum_ccdc_archive 'CCDC 769480' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetraacetyl-1,8-diaminooctane ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H28 N2 O4' _chemical_formula_sum 'C16 H28 N2 O4' _chemical_formula_weight 312.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 20.0183(5) _cell_length_b 4.54300(10) _cell_length_c 20.5970(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.9860(10) _cell_angle_gamma 90.00 _cell_volume 1748.90(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5541 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 67.70 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.085 _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 150(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 10247 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2999 _reflns_number_gt 2538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0700P)^2^+0.6000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2999 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 C11 C 0.63791(10) -0.0348(4) 0.37191(9) 0.0321(4) Uani 1 1 d . . . H11A H 0.6654 -0.2013 0.3999 0.039 Uiso 1 1 calc R . . H11B H 0.6005 -0.1172 0.3301 0.039 Uiso 1 1 calc R . . N11 N 0.68645(7) 0.1522(3) 0.35007(7) 0.0289(3) Uani 1 1 d . . . C12 C 0.60239(10) 0.1350(4) 0.41449(9) 0.0328(4) Uani 1 1 d . . . H12A H 0.6398 0.2231 0.4555 0.039 Uiso 1 1 calc R . . H12B H 0.5735 0.2974 0.3859 0.039 Uiso 1 1 calc R . . C13 C 0.55436(9) -0.0608(4) 0.43894(9) 0.0307(4) Uani 1 1 d . . . H13A H 0.5823 -0.2328 0.4637 0.037 Uiso 1 1 calc R . . H13B H 0.5146 -0.1348 0.3978 0.037 Uiso 1 1 calc R . . C14 C 0.52329(9) 0.0979(4) 0.48687(9) 0.0320(4) Uani 1 1 d . . . H14A H 0.5631 0.1767 0.5273 0.048 Uiso 1 1 calc R . . H14B H 0.4944 0.2670 0.4616 0.048 Uiso 1 1 calc R . . C21 C 0.75714(10) 0.1698(5) 0.39710(9) 0.0385(5) Uani 1 1 d . . . O21 O 0.77243(8) 0.0543(4) 0.45346(7) 0.0599(5) Uani 1 1 d . . . C22 C 0.81267(10) 0.3188(6) 0.37580(10) 0.0518(6) Uani 1 1 d . . . H22A H 0.8057 0.2654 0.3277 0.078 Uiso 1 1 calc R . . H22B H 0.8604 0.2561 0.4065 0.078 Uiso 1 1 calc R . . H22C H 0.8083 0.5326 0.3792 0.078 Uiso 1 1 calc R . . C31 C 0.66057(10) 0.3160(4) 0.28841(9) 0.0339(4) Uani 1 1 d . . . O31 O 0.69344(8) 0.5208(3) 0.27731(7) 0.0474(4) Uani 1 1 d . . . C32 C 0.58909(11) 0.2306(6) 0.23652(11) 0.0534(6) Uani 1 1 d . . . H32A H 0.5772 0.3593 0.1958 0.080 Uiso 1 1 calc R . . H32B H 0.5525 0.2507 0.2576 0.080 Uiso 1 1 calc R . . H32C H 0.5908 0.0258 0.2222 0.080 Uiso 1 1 calc R . . C41 C 0.37726(10) 0.9952(4) 0.14289(9) 0.0310(4) Uani 1 1 d . . . H41A H 0.4143 1.1173 0.1771 0.037 Uiso 1 1 calc R . . H41B H 0.3392 1.1287 0.1137 0.037 Uiso 1 1 calc R . . N41 N 0.34620(7) 0.7908(3) 0.18053(7) 0.0302(4) Uani 1 1 d . . . C42 C 0.41070(9) 0.8362(4) 0.09677(9) 0.0308(4) Uani 1 1 d . . . H42A H 0.4473 0.6962 0.1254 0.037 Uiso 1 1 calc R . . H42B H 0.3733 0.7216 0.0610 0.037 Uiso 1 1 calc R . . C43 C 0.44517(9) 1.0494(4) 0.06127(8) 0.0284(4) Uani 1 1 d . . . H43A H 0.4817 1.1668 0.0972 0.034 Uiso 1 1 calc R . . H43B H 0.4082 1.1870 0.0321 0.034 Uiso 1 1 calc R . . C44 C 0.48030(9) 0.8959(4) 0.01587(8) 0.0285(4) Uani 1 1 d . . . H44A H 0.5145 0.7474 0.0443 0.043 Uiso 1 1 calc R . . H44B H 0.4430 0.7904 -0.0221 0.043 Uiso 1 1 calc R . . C51 C 0.39467(10) 0.6827(4) 0.24399(9) 0.0343(4) Uani 1 1 d . . . O51 O 0.45771(7) 0.7441(4) 0.26050(7) 0.0470(4) Uani 1 1 d . . . C52 C 0.36820(12) 0.5068(5) 0.29157(10) 0.0452(5) Uani 1 1 d . . . H52A H 0.3531 0.3115 0.2714 0.068 Uiso 1 1 calc R . . H52B H 0.3275 0.6082 0.2974 0.068 Uiso 1 1 calc R . . H52C H 0.4067 0.4857 0.3369 0.068 Uiso 1 1 calc R . . C61 C 0.27541(10) 0.6925(4) 0.14974(9) 0.0354(4) Uani 1 1 d . . . O61 O 0.25186(8) 0.4943(3) 0.17429(8) 0.0503(4) Uani 1 1 d . . . C62 C 0.22901(11) 0.8411(5) 0.08378(10) 0.0475(5) Uani 1 1 d . . . H62A H 0.1805 0.7593 0.0690 0.071 Uiso 1 1 calc R . . H62B H 0.2490 0.8078 0.0473 0.071 Uiso 1 1 calc R . . H62C H 0.2273 1.0529 0.0920 0.071 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 C11 0.0353(10) 0.0314(10) 0.0356(9) -0.0007(7) 0.0199(8) -0.0040(7) N11 0.0291(8) 0.0330(8) 0.0276(7) -0.0011(6) 0.0140(6) -0.0013(6) C12 0.0377(10) 0.0298(10) 0.0366(9) -0.0030(7) 0.0203(8) -0.0037(7) C13 0.0338(9) 0.0311(10) 0.0315(9) -0.0027(7) 0.0168(7) -0.0034(7) C14 0.0366(10) 0.0304(10) 0.0334(9) -0.0017(7) 0.0181(8) -0.0021(8) C21 0.0337(10) 0.0532(13) 0.0308(10) -0.0041(8) 0.0140(8) -0.0012(9) O21 0.0426(9) 0.0964(13) 0.0369(8) 0.0177(8) 0.0095(6) 0.0010(8) C22 0.0336(11) 0.0849(18) 0.0389(11) -0.0094(11) 0.0154(9) -0.0130(11) C31 0.0359(10) 0.0393(11) 0.0315(9) 0.0003(8) 0.0181(8) 0.0030(8) O31 0.0531(9) 0.0465(9) 0.0490(8) 0.0110(6) 0.0261(7) -0.0035(7) C32 0.0447(12) 0.0712(16) 0.0366(11) 0.0079(10) 0.0053(9) -0.0007(11) C41 0.0344(9) 0.0295(10) 0.0343(9) -0.0026(7) 0.0186(8) -0.0018(7) N41 0.0314(8) 0.0315(9) 0.0320(8) -0.0042(6) 0.0167(6) -0.0022(6) C42 0.0333(9) 0.0306(10) 0.0313(9) -0.0024(7) 0.0151(7) 0.0008(7) C43 0.0304(9) 0.0295(9) 0.0268(8) -0.0013(7) 0.0121(7) 0.0013(7) C44 0.0280(9) 0.0293(10) 0.0293(8) -0.0013(7) 0.0117(7) 0.0026(7) C51 0.0379(11) 0.0358(11) 0.0328(9) -0.0051(7) 0.0172(8) 0.0003(8) O51 0.0347(8) 0.0674(10) 0.0380(7) 0.0003(7) 0.0119(6) -0.0061(7) C52 0.0531(13) 0.0488(13) 0.0403(10) 0.0040(9) 0.0247(10) 0.0001(9) C61 0.0334(10) 0.0372(11) 0.0410(10) -0.0117(8) 0.0200(8) -0.0034(8) O61 0.0414(8) 0.0496(10) 0.0636(9) -0.0022(7) 0.0232(7) -0.0138(6) C62 0.0358(11) 0.0605(15) 0.0435(11) -0.0093(10) 0.0110(9) -0.0011(9) _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 C11 N11 1.477(2) . ? C11 C12 1.522(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C31 1.401(2) . ? N11 C21 1.402(2) . ? C12 C13 1.522(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.523(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C14 1.521(3) 3_656 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C21 O21 1.209(2) . ? C21 C22 1.495(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 O31 1.208(2) . ? C31 C32 1.498(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 N41 1.482(2) . ? C41 C42 1.526(2) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? N41 C61 1.402(2) . ? N41 C51 1.408(2) . ? C42 C43 1.520(2) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.525(2) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C44 1.521(3) 3_675 ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C51 O51 1.216(2) . ? C51 C52 1.501(3) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C61 O61 1.208(2) . ? C61 C62 1.503(3) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 N11 C11 C12 112.21(14) . . ? N11 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N11 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C31 N11 C21 123.37(15) . . ? C31 N11 C11 120.76(14) . . ? C21 N11 C11 115.70(14) . . ? C13 C12 C11 112.04(15) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 113.00(14) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C14 C14 C13 113.48(18) 3_656 . ? C14 C14 H14A 108.9 3_656 . ? C13 C14 H14A 108.9 . . ? C14 C14 H14B 108.9 3_656 . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? O21 C21 N11 118.97(17) . . ? O21 C21 C22 121.27(18) . . ? N11 C21 C22 119.71(16) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O31 C31 N11 122.06(17) . . ? O31 C31 C32 120.69(18) . . ? N11 C31 C32 117.24(17) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N41 C41 C42 112.88(14) . . ? N41 C41 H41A 109.0 . . ? C42 C41 H41A 109.0 . . ? N41 C41 H41B 109.0 . . ? C42 C41 H41B 109.0 . . ? H41A C41 H41B 107.8 . . ? C61 N41 C51 123.90(15) . . ? C61 N41 C41 120.56(15) . . ? C51 N41 C41 115.18(14) . . ? C43 C42 C41 111.94(14) . . ? C43 C42 H42A 109.2 . . ? C41 C42 H42A 109.2 . . ? C43 C42 H42B 109.2 . . ? C41 C42 H42B 109.2 . . ? H42A C42 H42B 107.9 . . ? C42 C43 C44 113.09(14) . . ? C42 C43 H43A 109.0 . . ? C44 C43 H43A 109.0 . . ? C42 C43 H43B 109.0 . . ? C44 C43 H43B 109.0 . . ? H43A C43 H43B 107.8 . . ? C44 C44 C43 113.79(18) 3_675 . ? C44 C44 H44A 108.8 3_675 . ? C43 C44 H44A 108.8 . . ? C44 C44 H44B 108.8 3_675 . ? C43 C44 H44B 108.8 . . ? H44A C44 H44B 107.7 . . ? O51 C51 N41 118.72(16) . . ? O51 C51 C52 120.90(17) . . ? N41 C51 C52 120.32(16) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O61 C61 N41 122.04(18) . . ? O61 C61 C62 120.36(17) . . ? N41 C61 C62 117.59(17) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? 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 C12 C11 N11 C31 -87.29(19) . . . . ? C12 C11 N11 C21 88.16(19) . . . . ? N11 C11 C12 C13 -178.09(14) . . . . ? C11 C12 C13 C14 175.01(15) . . . . ? C12 C13 C14 C14 -178.52(18) . . . 3_656 ? C31 N11 C21 O21 169.52(19) . . . . ? C11 N11 C21 O21 -5.8(3) . . . . ? C31 N11 C21 C22 -13.1(3) . . . . ? C11 N11 C21 C22 171.56(17) . . . . ? C21 N11 C31 O31 -13.3(3) . . . . ? C11 N11 C31 O31 161.79(16) . . . . ? C21 N11 C31 C32 167.77(18) . . . . ? C11 N11 C31 C32 -17.1(2) . . . . ? C42 C41 N41 C61 -87.67(19) . . . . ? C42 C41 N41 C51 85.69(18) . . . . ? N41 C41 C42 C43 -177.40(14) . . . . ? C41 C42 C43 C44 178.90(14) . . . . ? C42 C43 C44 C44 -175.80(17) . . . 3_675 ? C61 N41 C51 O51 167.66(16) . . . . ? C41 N41 C51 O51 -5.4(2) . . . . ? C61 N41 C51 C52 -15.1(3) . . . . ? C41 N41 C51 C52 171.81(16) . . . . ? C51 N41 C61 O61 -3.9(3) . . . . ? C41 N41 C61 O61 168.87(16) . . . . ? C51 N41 C61 C62 176.76(16) . . . . ? C41 N41 C61 C62 -10.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.180 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.048 #END data_ih0536m(8) _database_code_depnum_ccdc_archive 'CCDC 769481' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Zn(OH2)2 (Ac2N-(CH2)6-NAc2) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; Zn (H2 O)2 (C14 H24 N2 O4) (Cl O4)2 ; _chemical_formula_sum 'C14 H28 Cl2 N2 O14 Zn' _chemical_formula_weight 584.65 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 20.223(3) _cell_length_b 7.9438(12) _cell_length_c 14.875(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.797(9) _cell_angle_gamma 90.00 _cell_volume 2367.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2255 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.333 _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 173(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 16436 _diffrn_reflns_av_R_equivalents 0.1738 _diffrn_reflns_av_sigmaI/netI 0.1738 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.17 _reflns_number_total 5433 _reflns_number_gt 2641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0900P)^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 SHELXL _refine_ls_extinction_coef 0.0108(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5433 _refine_ls_number_parameters 338 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.1386 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1895 _refine_ls_wR_factor_gt 0.1623 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.878 _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 Zn1 Zn 0.24372(3) 0.61355(8) 0.73302(4) 0.0292(2) Uani 1 1 d . . . O1 O 0.3132(2) 0.7602(5) 0.6837(3) 0.0431(10) Uani 1 1 d D . . H1A H 0.3530(13) 0.730(8) 0.683(3) 0.052 Uiso 1 1 d D . . H1B H 0.294(2) 0.769(8) 0.6314(19) 0.052 Uiso 1 1 d D . . O2 O 0.1903(2) 0.8177(5) 0.7595(3) 0.0419(10) Uani 1 1 d D . . H2A H 0.1506(13) 0.798(8) 0.768(4) 0.050 Uiso 1 1 d D . . H2B H 0.210(2) 0.867(7) 0.806(3) 0.050 Uiso 1 1 d D . . Cl1 Cl 0.0000 0.3115(3) 0.2500 0.0405(5) Uani 1 2 d S . . O13 O 0.0563(2) 0.2054(6) 0.2791(3) 0.0633(14) Uani 1 1 d . . . O14 O 0.0136(3) 0.4147(6) 0.1767(3) 0.0646(14) Uani 1 1 d . . . Cl2A Cl 0.5032(8) 0.6932(18) 0.7358(10) 0.0339(10) Uiso 0.218(11) 1 d PD A -1 O21A O 0.4791(12) 0.636(3) 0.6461(13) 0.071(8) Uiso 0.218(11) 1 d PD A -1 O22A O 0.5647(10) 0.773(2) 0.7211(15) 0.050(7) Uiso 0.218(11) 1 d PD A -1 O23A O 0.5231(11) 0.551(2) 0.7923(11) 0.044(6) Uiso 0.218(11) 1 d PD A -1 O24A O 0.4569(13) 0.802(3) 0.765(2) 0.096(13) Uiso 0.218(11) 1 d PD A -1 Cl2B Cl 0.4992(9) 0.7087(13) 0.7588(11) 0.0339(10) Uiso 0.282(11) 1 d PD A -2 O21B O 0.5229(12) 0.871(2) 0.7421(17) 0.111(10) Uiso 0.282(11) 1 d PD A -2 O22B O 0.5520(10) 0.595(3) 0.7878(14) 0.068(7) Uiso 0.282(11) 1 d PD A -2 O23B O 0.4591(10) 0.722(3) 0.8318(14) 0.089(8) Uiso 0.282(11) 1 d PD A -2 O24B O 0.4568(12) 0.640(2) 0.6820(13) 0.069(7) Uiso 0.282(11) 1 d PD A -2 Cl3 Cl 0.25367(8) -0.0620(2) 0.45448(10) 0.0453(4) Uani 1 1 d . . . O33 O 0.2734(3) -0.0356(9) 0.3670(4) 0.116(3) Uani 1 1 d . . . O34 O 0.1843(3) -0.0527(8) 0.4480(4) 0.0884(19) Uani 1 1 d . . . O35 O 0.2785(3) -0.2197(7) 0.4837(4) 0.090(2) Uani 1 1 d . . . O36 O 0.2811(4) 0.0545(11) 0.5148(6) 0.154(3) Uani 1 1 d . . . C11 C 0.1006(3) 0.1900(7) 0.5764(4) 0.0417(15) Uani 1 1 d D . . H11A H 0.1055 0.0914 0.6175 0.050 Uiso 1 1 calc R B 1 H11B H 0.1223 0.1619 0.5225 0.050 Uiso 1 1 calc R B 1 N11 N 0.1357(2) 0.3360(5) 0.6237(3) 0.0301(11) Uani 1 1 d . C . C12A C 0.0274(3) 0.2222(7) 0.5468(4) 0.0431(15) Uani 0.706(10) 1 d PD C 1 H12A H 0.0218 0.2850 0.4888 0.052 Uiso 0.706(10) 1 calc PR C 1 H12B H 0.0094 0.2924 0.5928 0.052 Uiso 0.706(10) 1 calc PR C 1 C13A C -0.0125(4) 0.0540(9) 0.5343(5) 0.037(2) Uani 0.706(10) 1 d PD . 1 H13A H -0.0085 -0.0066 0.5929 0.044 Uiso 0.706(10) 1 calc PR C 1 H13B H -0.0603 0.0789 0.5152 0.044 Uiso 0.706(10) 1 calc PR C 1 C12B C 0.0274(3) 0.2222(7) 0.5468(4) 0.0431(15) Uani 0.294(10) 1 d PD C 2 H12C H 0.0215 0.3348 0.5184 0.052 Uiso 0.294(10) 1 calc PR C 2 H12D H 0.0033 0.2208 0.6004 0.052 Uiso 0.294(10) 1 calc PR C 2 C13B C -0.0023(9) 0.0863(12) 0.4780(10) 0.037(2) Uani 0.294(10) 1 d PD . 2 H13C H -0.0497 0.1131 0.4565 0.044 Uiso 0.294(10) 1 calc PR C 2 H13D H 0.0223 0.0861 0.4248 0.044 Uiso 0.294(10) 1 calc PR C 2 C21 C 0.1635(3) 0.4559(8) 0.5727(4) 0.0357(13) Uani 1 1 d . . . O21 O 0.19533(19) 0.5765(5) 0.6065(2) 0.0354(9) Uani 1 1 d . C . C22 C 0.1554(4) 0.4368(10) 0.4721(4) 0.062(2) Uani 1 1 d . C . H22A H 0.1619 0.5463 0.4441 0.092 Uiso 1 1 calc R . . H22B H 0.1105 0.3950 0.4506 0.092 Uiso 1 1 calc R . . H22C H 0.1886 0.3567 0.4555 0.092 Uiso 1 1 calc R . . O22 O 0.16738(19) 0.4589(5) 0.7621(2) 0.0335(9) Uani 1 1 d . C . C23 C 0.1366(3) 0.3514(6) 0.7171(4) 0.0294(12) Uani 1 1 d . . . C24 C 0.0957(4) 0.2306(8) 0.7645(4) 0.0508(17) Uani 1 1 d . C . H24A H 0.0861 0.2806 0.8215 0.076 Uiso 1 1 calc R . . H24B H 0.1207 0.1257 0.7774 0.076 Uiso 1 1 calc R . . H24C H 0.0537 0.2067 0.7255 0.076 Uiso 1 1 calc R . . C31 C 0.4385(3) 0.3156(8) 0.8906(4) 0.0454(16) Uani 1 1 d . . . H31A H 0.4614 0.4013 0.9320 0.054 Uiso 1 1 calc R . . H31B H 0.4669 0.2938 0.8427 0.054 Uiso 1 1 calc R . . N31 N 0.3741(2) 0.3873(6) 0.8473(3) 0.0337(11) Uani 1 1 d . . . C32 C 0.4336(3) 0.1547(8) 0.9438(4) 0.0457(16) Uani 1 1 d . . . H32A H 0.4117 0.1787 0.9980 0.055 Uiso 1 1 calc R . . H32B H 0.4056 0.0724 0.9057 0.055 Uiso 1 1 calc R . . C33 C 0.5017(3) 0.0795(7) 0.9732(4) 0.0455(17) Uani 1 1 d . . . H33A H 0.5233 0.0552 0.9188 0.055 Uiso 1 1 calc R . . H33B H 0.5296 0.1628 1.0105 0.055 Uiso 1 1 calc R . . C41 C 0.3473(3) 0.3309(7) 0.7617(4) 0.0349(13) Uani 1 1 d . . . O41 O 0.2996(2) 0.3951(5) 0.7169(2) 0.0377(10) Uani 1 1 d . . . C42 C 0.3809(4) 0.1878(9) 0.7205(5) 0.063(2) Uani 1 1 d . . . H42A H 0.3502 0.1389 0.6708 0.095 Uiso 1 1 calc R . . H42B H 0.3937 0.1017 0.7668 0.095 Uiso 1 1 calc R . . H42C H 0.4209 0.2293 0.6970 0.095 Uiso 1 1 calc R . . O42 O 0.2941(2) 0.5869(5) 0.8596(2) 0.0374(10) Uani 1 1 d . . . C43 C 0.3424(3) 0.5062(7) 0.8949(4) 0.0339(13) Uani 1 1 d . . . C44 C 0.3672(3) 0.5398(8) 0.9913(4) 0.0519(18) Uani 1 1 d . . . H44A H 0.4079 0.6078 0.9956 0.078 Uiso 1 1 calc R . . H44B H 0.3770 0.4329 1.0232 0.078 Uiso 1 1 calc R . . H44C H 0.3331 0.6009 1.0191 0.078 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 Zn1 0.0305(4) 0.0275(4) 0.0280(3) -0.0038(3) -0.0017(3) -0.0003(3) O1 0.034(3) 0.047(3) 0.046(2) 0.005(2) -0.004(2) -0.004(2) O2 0.032(2) 0.039(2) 0.053(3) -0.0173(19) -0.003(2) 0.000(2) Cl1 0.0381(13) 0.0320(11) 0.0507(13) 0.000 0.0032(10) 0.000 O13 0.039(3) 0.052(3) 0.100(4) 0.029(3) 0.015(3) 0.012(2) O14 0.082(4) 0.055(3) 0.053(3) 0.017(2) -0.005(3) -0.009(3) Cl3 0.0459(10) 0.0424(9) 0.0452(9) 0.0065(6) -0.0029(7) 0.0087(7) O33 0.117(5) 0.154(6) 0.086(4) 0.081(4) 0.049(4) 0.078(5) O34 0.047(3) 0.134(5) 0.083(4) -0.030(4) 0.003(3) 0.040(3) O35 0.080(4) 0.061(4) 0.140(5) 0.049(3) 0.058(4) 0.032(3) O36 0.142(7) 0.152(7) 0.154(7) -0.090(6) -0.034(6) -0.032(6) C11 0.045(4) 0.034(3) 0.047(3) -0.019(3) 0.009(3) -0.010(3) N11 0.028(3) 0.029(2) 0.034(2) -0.0079(18) 0.007(2) -0.004(2) C12A 0.041(4) 0.034(3) 0.054(4) -0.019(3) 0.005(3) -0.009(3) C13A 0.038(5) 0.043(5) 0.031(4) -0.014(4) 0.009(4) -0.012(4) C12B 0.041(4) 0.034(3) 0.054(4) -0.019(3) 0.005(3) -0.009(3) C13B 0.038(5) 0.043(5) 0.031(4) -0.014(4) 0.009(4) -0.012(4) C21 0.029(3) 0.049(4) 0.029(3) -0.004(3) 0.001(3) -0.006(3) O21 0.038(2) 0.041(2) 0.0253(19) 0.0013(16) -0.0045(17) -0.0147(19) C22 0.058(5) 0.092(6) 0.035(3) -0.012(3) 0.005(3) -0.031(4) O22 0.036(2) 0.036(2) 0.0271(19) -0.0033(16) -0.0032(17) -0.0067(18) C23 0.027(3) 0.028(3) 0.031(3) 0.003(2) -0.002(2) 0.003(2) C24 0.058(5) 0.046(4) 0.049(4) 0.011(3) 0.008(3) -0.015(3) C31 0.026(3) 0.051(4) 0.058(4) 0.023(3) 0.000(3) 0.000(3) N31 0.027(3) 0.036(3) 0.038(3) 0.009(2) 0.003(2) 0.000(2) C32 0.032(4) 0.047(4) 0.056(4) 0.024(3) -0.002(3) 0.003(3) C33 0.028(3) 0.050(4) 0.059(4) 0.027(3) 0.005(3) 0.002(3) C41 0.033(4) 0.033(3) 0.039(3) -0.002(2) 0.009(3) 0.002(3) O41 0.038(2) 0.039(2) 0.034(2) -0.0075(17) -0.0003(19) 0.0094(19) C42 0.074(6) 0.056(4) 0.062(4) -0.003(3) 0.017(4) 0.027(4) O42 0.040(2) 0.040(2) 0.029(2) -0.0081(16) -0.0038(18) 0.0048(19) C43 0.032(3) 0.030(3) 0.036(3) 0.004(2) -0.006(3) -0.006(3) C44 0.067(5) 0.043(4) 0.040(4) -0.004(3) -0.016(3) -0.009(3) _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 Zn1 O2 2.017(4) . ? Zn1 O21 2.022(4) . ? Zn1 O42 2.027(4) . ? Zn1 O1 2.038(4) . ? Zn1 O22 2.064(4) . ? Zn1 O41 2.103(4) . ? O1 H1A 0.842(19) . ? O1 H1B 0.822(19) . ? O2 H2A 0.843(19) . ? O2 H2B 0.839(19) . ? Cl1 O14 1.420(4) . ? Cl1 O14 1.420(4) 2 ? Cl1 O13 1.436(4) 2 ? Cl1 O13 1.436(4) . ? Cl2A O24A 1.388(16) . ? Cl2A O23A 1.432(15) . ? Cl2A O21A 1.432(16) . ? Cl2A O22A 1.439(16) . ? Cl2B O21B 1.407(15) . ? Cl2B O22B 1.421(16) . ? Cl2B O24B 1.438(16) . ? Cl2B O23B 1.444(16) . ? Cl3 O36 1.355(6) . ? Cl3 O34 1.395(5) . ? Cl3 O35 1.397(5) . ? Cl3 O33 1.428(5) . ? C11 N11 1.486(7) . ? C11 C12A 1.509(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C21 1.384(7) . ? N11 C23 1.393(6) . ? C12A C13A 1.559(8) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C13A 1.474(12) 3_556 ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C13B C13B 1.516(18) 3_556 ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C21 O21 1.223(6) . ? C21 C22 1.490(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O22 C23 1.205(6) . ? C23 C24 1.502(7) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C31 N31 1.485(7) . ? C31 C32 1.513(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? N31 C41 1.388(7) . ? N31 C43 1.389(7) . ? C32 C33 1.510(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C33 1.501(10) 3_657 ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C41 O41 1.208(7) . ? C41 C42 1.498(8) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? O42 C43 1.225(6) . ? C43 C44 1.478(8) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? 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 O2 Zn1 O21 95.44(17) . . ? O2 Zn1 O42 96.76(16) . . ? O21 Zn1 O42 165.59(16) . . ? O2 Zn1 O1 91.40(18) . . ? O21 Zn1 O1 91.06(16) . . ? O42 Zn1 O1 96.28(17) . . ? O2 Zn1 O22 90.12(16) . . ? O21 Zn1 O22 80.04(14) . . ? O42 Zn1 O22 92.27(15) . . ? O1 Zn1 O22 171.07(16) . . ? O2 Zn1 O41 175.18(16) . . ? O21 Zn1 O41 88.49(15) . . ? O42 Zn1 O41 78.98(15) . . ? O1 Zn1 O41 91.32(16) . . ? O22 Zn1 O41 87.80(16) . . ? Zn1 O1 H1A 123(4) . . ? Zn1 O1 H1B 98(4) . . ? H1A O1 H1B 110(3) . . ? Zn1 O2 H2A 115(4) . . ? Zn1 O2 H2B 109(4) . . ? H2A O2 H2B 109(3) . . ? O14 Cl1 O14 109.4(4) . 2 ? O14 Cl1 O13 109.6(3) . 2 ? O14 Cl1 O13 110.0(3) 2 2 ? O14 Cl1 O13 110.0(3) . . ? O14 Cl1 O13 109.6(3) 2 . ? O13 Cl1 O13 108.1(4) 2 . ? O24A Cl2A O23A 116.8(14) . . ? O24A Cl2A O21A 109.4(14) . . ? O23A Cl2A O21A 109.2(12) . . ? O24A Cl2A O22A 114.1(14) . . ? O23A Cl2A O22A 105.1(13) . . ? O21A Cl2A O22A 101.0(12) . . ? O21B Cl2B O22B 111.9(14) . . ? O21B Cl2B O24B 112.6(13) . . ? O22B Cl2B O24B 110.1(11) . . ? O21B Cl2B O23B 107.8(13) . . ? O22B Cl2B O23B 107.1(12) . . ? O24B Cl2B O23B 106.9(13) . . ? O36 Cl3 O34 109.1(4) . . ? O36 Cl3 O35 108.0(5) . . ? O34 Cl3 O35 112.6(4) . . ? O36 Cl3 O33 111.3(6) . . ? O34 Cl3 O33 109.4(4) . . ? O35 Cl3 O33 106.4(4) . . ? N11 C11 C12A 113.1(5) . . ? N11 C11 H11A 109.0 . . ? C12A C11 H11A 109.0 . . ? N11 C11 H11B 109.0 . . ? C12A C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C21 N11 C23 122.4(4) . . ? C21 N11 C11 118.8(5) . . ? C23 N11 C11 118.8(5) . . ? C11 C12A C13A 111.2(5) . . ? C11 C12A H12A 109.4 . . ? C13A C12A H12A 109.4 . . ? C11 C12A H12B 109.4 . . ? C13A C12A H12B 109.4 . . ? H12A C12A H12B 108.0 . . ? C13A C13A C12A 111.1(7) 3_556 . ? C13A C13A H13A 109.4 3_556 . ? C12A C13A H13A 109.4 . . ? C13A C13A H13B 109.4 3_556 . ? C12A C13A H13B 109.4 . . ? H13A C13A H13B 108.0 . . ? C13B C13B H13C 109.6 3_556 . ? C13B C13B H13D 109.6 3_556 . ? H13C C13B H13D 108.1 . . ? O21 C21 N11 122.9(5) . . ? O21 C21 C22 118.2(5) . . ? N11 C21 C22 118.9(5) . . ? C21 O21 Zn1 131.1(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 O22 Zn1 130.6(4) . . ? O22 C23 N11 123.5(5) . . ? O22 C23 C24 117.9(5) . . ? N11 C23 C24 118.6(5) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N31 C31 C32 115.8(5) . . ? N31 C31 H31A 108.3 . . ? C32 C31 H31A 108.3 . . ? N31 C31 H31B 108.3 . . ? C32 C31 H31B 108.3 . . ? H31A C31 H31B 107.4 . . ? C41 N31 C43 122.4(5) . . ? C41 N31 C31 119.0(5) . . ? C43 N31 C31 118.5(5) . . ? C33 C32 C31 111.3(5) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C33 C33 C32 112.4(6) 3_657 . ? C33 C33 H33A 109.1 3_657 . ? C32 C33 H33A 109.1 . . ? C33 C33 H33B 109.1 3_657 . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? O41 C41 N31 123.6(5) . . ? O41 C41 C42 117.9(6) . . ? N31 C41 C42 118.5(6) . . ? C41 O41 Zn1 133.4(4) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C43 O42 Zn1 136.4(4) . . ? O42 C43 N31 122.3(5) . . ? O42 C43 C44 117.8(5) . . ? N31 C43 C44 119.9(5) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? 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 C12A C11 N11 C21 -89.3(6) . . . . ? C12A C11 N11 C23 87.7(6) . . . . ? N11 C11 C12A C13A -157.1(5) . . . . ? C11 C12A C13A C13A -59.4(11) . . . 3_556 ? C23 N11 C21 O21 5.9(9) . . . . ? C11 N11 C21 O21 -177.2(5) . . . . ? C23 N11 C21 C22 -174.9(6) . . . . ? C11 N11 C21 C22 2.0(8) . . . . ? N11 C21 O21 Zn1 22.0(9) . . . . ? C22 C21 O21 Zn1 -157.2(5) . . . . ? O2 Zn1 O21 C21 -120.7(5) . . . . ? O42 Zn1 O21 C21 27.1(9) . . . . ? O1 Zn1 O21 C21 147.8(5) . . . . ? O22 Zn1 O21 C21 -31.5(5) . . . . ? O41 Zn1 O21 C21 56.5(5) . . . . ? O2 Zn1 O22 C23 124.2(5) . . . . ? O21 Zn1 O22 C23 28.7(5) . . . . ? O42 Zn1 O22 C23 -139.0(5) . . . . ? O41 Zn1 O22 C23 -60.1(5) . . . . ? Zn1 O22 C23 N11 -16.6(8) . . . . ? Zn1 O22 C23 C24 165.0(4) . . . . ? C21 N11 C23 O22 -8.2(9) . . . . ? C11 N11 C23 O22 174.9(5) . . . . ? C21 N11 C23 C24 170.2(5) . . . . ? C11 N11 C23 C24 -6.7(8) . . . . ? C32 C31 N31 C41 -86.4(7) . . . . ? C32 C31 N31 C43 92.3(7) . . . . ? N31 C31 C32 C33 171.7(6) . . . . ? C31 C32 C33 C33 179.5(7) . . . 3_657 ? C43 N31 C41 O41 10.2(8) . . . . ? C31 N31 C41 O41 -171.2(5) . . . . ? C43 N31 C41 C42 -172.7(5) . . . . ? C31 N31 C41 C42 5.9(8) . . . . ? N31 C41 O41 Zn1 7.0(9) . . . . ? C42 C41 O41 Zn1 -170.1(4) . . . . ? O21 Zn1 O41 C41 172.0(5) . . . . ? O42 Zn1 O41 C41 -15.2(5) . . . . ? O1 Zn1 O41 C41 80.9(5) . . . . ? O22 Zn1 O41 C41 -107.9(5) . . . . ? O2 Zn1 O42 C43 -167.4(5) . . . . ? O21 Zn1 O42 C43 44.9(10) . . . . ? O1 Zn1 O42 C43 -75.3(6) . . . . ? O22 Zn1 O42 C43 102.2(6) . . . . ? O41 Zn1 O42 C43 14.9(5) . . . . ? Zn1 O42 C43 N31 -5.9(9) . . . . ? Zn1 O42 C43 C44 173.5(4) . . . . ? C41 N31 C43 O42 -11.1(8) . . . . ? C31 N31 C43 O42 170.3(5) . . . . ? C41 N31 C43 C44 169.5(5) . . . . ? C31 N31 C43 C44 -9.2(7) . . . . ? 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 O1 H1A O22A 0.842(19) 2.06(5) 2.68(2) 129(5) 2_656 O1 H1A O22B 0.842(19) 2.19(3) 3.00(2) 163(6) 2_656 O1 H1A O24B 0.842(19) 2.22(3) 3.06(3) 178(6) . O1 H1B O35 0.822(19) 2.18(3) 2.967(7) 161(5) 1_565 O2 H2A O13 0.843(19) 1.94(2) 2.770(6) 169(6) 4_566 O2 H2B O33 0.839(19) 1.99(3) 2.765(6) 153(5) 4_566 _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.727 _refine_diff_density_min -0.822 _refine_diff_density_rms 0.151 #END