# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '19602_web_deposit_cif_file_0_GanesanPrabusankar_1366283649.2.cif' data_2 #TrackingRef '19602_web_deposit_cif_file_0_GanesanPrabusankar_1366283649.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 Br2 N4 O4' _chemical_formula_weight 672.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6681(2) _cell_length_b 11.6004(7) _cell_length_c 13.7298(8) _cell_angle_alpha 99.221(5) _cell_angle_beta 93.928(4) _cell_angle_gamma 96.670(4) _cell_volume 726.04(7) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4648 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 70.69 _exptl_crystal_description Rectangle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 3.888 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4820 _exptl_absorpt_correction_T_max 0.5214 _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4648 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 70.69 _reflns_number_total 2735 _reflns_number_gt 2589 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997); Diamond 3.2i (Brandenburg,1999) ; _computing_publication_material 'MERCURY (Macrae et al., 2006)' _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^)+(0.0856P)^2^+0.7723P] 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 2735 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2025(8) 0.5958(3) 0.1646(3) 0.0760(10) Uani 1 1 d . . . O2 O 0.5374(9) 0.4756(4) 0.1489(4) 0.0873(12) Uani 1 1 d . . . N1 N 0.2675(7) 0.3270(3) 0.2576(2) 0.0502(8) Uani 1 1 d . . . N2 N 0.5501(7) 0.2241(3) 0.3292(2) 0.0446(7) Uani 1 1 d . . . C1 C 0.1659(17) 0.7024(8) 0.0290(5) 0.114(3) Uani 1 1 d . . . H1A H 0.2702 0.7537 -0.0084 0.136 Uiso 1 1 d R . . H1B H 0.1477 0.6051 -0.0101 0.136 Uiso 1 1 d R . . H1C H 0.0084 0.7371 0.0552 0.136 Uiso 1 1 d R . . C2 C 0.3576(13) 0.6762(5) 0.1066(5) 0.0817(16) Uani 1 1 d . . . H2A H 0.4381 0.7487 0.1502 0.098 Uiso 1 1 calc R . . H2B H 0.5164 0.6399 0.0780 0.098 Uiso 1 1 calc R . . C3 C 0.3178(9) 0.5026(4) 0.1793(3) 0.0531(9) Uani 1 1 d . . . C4 C 0.1302(10) 0.4284(4) 0.2377(3) 0.0564(10) Uani 1 1 d . . . H4A H 0.0976 0.4758 0.2998 0.068 Uiso 1 1 calc R . . H4B H -0.0563 0.4015 0.2005 0.068 Uiso 1 1 calc R . . C5 C 0.2589(11) 0.2201(4) 0.1960(3) 0.0595(11) Uani 1 1 d . . . H5 H 0.1521 0.1967 0.1349 0.071 Uiso 1 1 calc R . . C6 C 0.4338(11) 0.1558(4) 0.2406(3) 0.0570(10) Uani 1 1 d . . . H6 H 0.4693 0.0797 0.2163 0.068 Uiso 1 1 calc R . . C7 C 0.4468(8) 0.3278(3) 0.3371(3) 0.0466(8) Uani 1 1 d . . . H7 H 0.4930 0.3901 0.3897 0.056 Uiso 1 1 calc R . . C8 C 0.7525(8) 0.1903(3) 0.4041(3) 0.0447(8) Uani 1 1 d . . . H8A H 0.8174 0.2585 0.4547 0.054 Uiso 1 1 calc R . . H8B H 0.9209 0.1664 0.3726 0.054 Uiso 1 1 calc R . . C9 C 0.6203(8) 0.0916(3) 0.4526(3) 0.0409(7) Uani 1 1 d . . . C10 C 0.6728(8) -0.0245(3) 0.4196(3) 0.0413(7) Uani 1 1 d . . . C11 C 0.8417(9) -0.0562(4) 0.3386(3) 0.0497(9) Uani 1 1 d . . . H11 H 0.9174 0.0020 0.3047 0.060 Uiso 1 1 calc R . . C12 C 0.8943(10) -0.1676(4) 0.3103(3) 0.0565(10) Uani 1 1 d . . . H12 H 1.0097 -0.1848 0.2586 0.068 Uiso 1 1 calc R . . C13 C 0.7768(10) -0.2582(4) 0.3579(3) 0.0554(10) Uani 1 1 d . . . H13 H 0.8142 -0.3349 0.3372 0.066 Uiso 1 1 calc R . . C14 C 0.6103(9) -0.2351(3) 0.4332(3) 0.0481(9) Uani 1 1 d . . . H14 H 0.5324 -0.2965 0.4632 0.058 Uiso 1 1 calc R . . C15 C 0.4495(8) 0.1175(3) 0.5316(3) 0.0424(8) Uani 1 1 d . . . Br1A Br 0.0000 0.5000 0.5000 0.0442(2) Uani 1 2 d S . . Br1B Br -0.1961(7) 0.96163(15) 0.06072(13) 0.1560(11) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.081(2) 0.064(2) 0.099(3) 0.0431(19) 0.021(2) 0.0271(17) O2 0.073(2) 0.083(3) 0.125(3) 0.056(2) 0.025(2) 0.026(2) N1 0.0574(19) 0.0471(18) 0.0480(17) 0.0153(14) -0.0028(14) 0.0089(15) N2 0.0496(17) 0.0346(15) 0.0505(17) 0.0131(13) -0.0008(13) 0.0046(12) C1 0.116(6) 0.153(7) 0.067(4) 0.045(4) -0.008(3) -0.030(5) C2 0.082(3) 0.069(3) 0.108(4) 0.047(3) 0.017(3) 0.015(3) C3 0.057(2) 0.050(2) 0.054(2) 0.0141(18) -0.0056(18) 0.0105(18) C4 0.064(3) 0.055(2) 0.055(2) 0.0200(19) -0.0002(19) 0.020(2) C5 0.078(3) 0.050(2) 0.049(2) 0.0087(18) -0.0122(19) 0.008(2) C6 0.078(3) 0.041(2) 0.050(2) 0.0073(17) -0.0049(19) 0.0083(19) C7 0.051(2) 0.0394(19) 0.051(2) 0.0143(16) 0.0001(16) 0.0063(15) C8 0.0464(19) 0.0325(17) 0.055(2) 0.0114(15) -0.0057(16) 0.0032(14) C9 0.0440(18) 0.0303(16) 0.0472(19) 0.0101(14) -0.0090(14) 0.0033(13) C10 0.0442(18) 0.0343(17) 0.0446(18) 0.0087(14) -0.0085(14) 0.0059(14) C11 0.057(2) 0.045(2) 0.049(2) 0.0136(16) 0.0001(17) 0.0083(17) C12 0.066(3) 0.052(2) 0.053(2) 0.0072(18) 0.0021(19) 0.022(2) C13 0.074(3) 0.037(2) 0.054(2) 0.0030(17) -0.0090(19) 0.0169(18) C14 0.061(2) 0.0317(18) 0.050(2) 0.0070(15) -0.0099(17) 0.0084(16) C15 0.0495(19) 0.0296(16) 0.0458(18) 0.0074(14) -0.0126(15) 0.0045(14) Br1A 0.0507(4) 0.0293(3) 0.0511(4) 0.0070(2) -0.0031(2) 0.0030(2) Br1B 0.282(3) 0.0789(10) 0.0847(10) -0.0113(8) 0.0333(14) -0.0455(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.300(5) . ? O1 C2 1.478(6) . ? O2 C3 1.189(6) . ? N1 C7 1.328(5) . ? N1 C5 1.380(6) . ? N1 C4 1.456(5) . ? N2 C7 1.339(5) . ? N2 C6 1.379(5) . ? N2 C8 1.478(5) . ? C1 C2 1.437(9) . ? C1 H1A 0.9593 . ? C1 H1B 1.1608 . ? C1 H1C 0.9433 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.514(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.349(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.507(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C15 1.405(5) . ? C9 C10 1.406(5) . ? C10 C11 1.431(6) . ? C10 C15 1.442(5) 2_656 ? C11 C12 1.345(6) . ? C11 H11 0.9300 . ? C12 C13 1.402(6) . ? C12 H12 0.9300 . ? C13 C14 1.348(6) . ? C13 H13 0.9300 . ? C14 C15 1.438(5) 2_656 ? C14 H14 0.9300 . ? C15 C14 1.438(5) 2_656 ? C15 C10 1.442(5) 2_656 ? Br1B Br1B 2.727(4) 2_575 ? 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 C3 O1 C2 117.8(4) . . ? C7 N1 C5 108.4(3) . . ? C7 N1 C4 124.0(4) . . ? C5 N1 C4 127.4(4) . . ? C7 N2 C6 108.3(3) . . ? C7 N2 C8 124.9(3) . . ? C6 N2 C8 126.7(3) . . ? C2 C1 H1A 109.9 . . ? C2 C1 H1B 89.5 . . ? H1A C1 H1B 110.7 . . ? C2 C1 H1C 111.0 . . ? H1A C1 H1C 110.3 . . ? H1B C1 H1C 123.4 . . ? C1 C2 O1 110.9(5) . . ? C1 C2 H2A 109.5 . . ? O1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? O1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O2 C3 O1 125.3(4) . . ? O2 C3 C4 123.4(4) . . ? O1 C3 C4 111.3(4) . . ? N1 C4 C3 110.9(4) . . ? N1 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 N1 107.5(4) . . ? C6 C5 H5 126.3 . . ? N1 C5 H5 126.3 . . ? C5 C6 N2 107.0(4) . . ? C5 C6 H6 126.5 . . ? N2 C6 H6 126.5 . . ? N1 C7 N2 108.7(4) . . ? N1 C7 H7 125.6 . . ? N2 C7 H7 125.6 . . ? N2 C8 C9 113.2(3) . . ? N2 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N2 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C15 C9 C10 120.8(3) . . ? C15 C9 C8 119.3(3) . . ? C10 C9 C8 119.9(3) . . ? C9 C10 C11 123.2(3) . . ? C9 C10 C15 119.2(3) . 2_656 ? C11 C10 C15 117.6(3) . 2_656 ? C12 C11 C10 121.9(4) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 121.5(4) . 2_656 ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 2_656 . ? C9 C15 C14 122.2(3) . 2_656 ? C9 C15 C10 120.0(3) . 2_656 ? C14 C15 C10 117.7(4) 2_656 2_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 C1 129.9(6) . . . . ? C2 O1 C3 O2 -1.0(8) . . . . ? C2 O1 C3 C4 -178.7(5) . . . . ? C7 N1 C4 C3 89.5(5) . . . . ? C5 N1 C4 C3 -84.0(5) . . . . ? O2 C3 C4 N1 4.7(7) . . . . ? O1 C3 C4 N1 -177.5(4) . . . . ? C7 N1 C5 C6 0.8(5) . . . . ? C4 N1 C5 C6 175.2(4) . . . . ? N1 C5 C6 N2 -0.4(5) . . . . ? C7 N2 C6 C5 -0.2(5) . . . . ? C8 N2 C6 C5 179.3(4) . . . . ? C5 N1 C7 N2 -0.9(5) . . . . ? C4 N1 C7 N2 -175.5(4) . . . . ? C6 N2 C7 N1 0.7(4) . . . . ? C8 N2 C7 N1 -178.8(3) . . . . ? C7 N2 C8 C9 113.7(4) . . . . ? C6 N2 C8 C9 -65.8(5) . . . . ? N2 C8 C9 C15 -82.4(4) . . . . ? N2 C8 C9 C10 98.6(4) . . . . ? C15 C9 C10 C11 179.2(3) . . . . ? C8 C9 C10 C11 -1.9(5) . . . . ? C15 C9 C10 C15 -0.4(6) . . . 2_656 ? C8 C9 C10 C15 178.5(3) . . . 2_656 ? C9 C10 C11 C12 178.3(4) . . . . ? C15 C10 C11 C12 -2.1(6) 2_656 . . . ? C10 C11 C12 C13 1.9(7) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C15 -0.9(6) . . . 2_656 ? C10 C9 C15 C14 -179.5(3) . . . 2_656 ? C8 C9 C15 C14 1.6(5) . . . 2_656 ? C10 C9 C15 C10 0.4(6) . . . 2_656 ? C8 C9 C15 C10 -178.5(3) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 70.69 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.102 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 924620' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Cu N7 O9' _chemical_formula_weight 726.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5604(7) _cell_length_b 12.3073(8) _cell_length_c 13.3623(8) _cell_angle_alpha 78.556(5) _cell_angle_beta 80.590(5) _cell_angle_gamma 67.806(6) _cell_volume 1717.07(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 7888 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 70.84 _exptl_crystal_description Block _exptl_crystal_colour 'Bluish green' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.435 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.595 _exptl_absorpt_correction_T_max 0.7060 _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ry Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method 'w\ scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7888 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0450 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 70.84 _reflns_number_total 6472 _reflns_number_gt 5494 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997); Diamond 3.2i (Brandenburg,1999) ; _computing_publication_material 'MERCURY (Macrae et al., 2006)' _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^)+(0.0858P)^2^+2.2347P] 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 6472 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.49525(4) 0.52218(4) 0.39885(3) 0.02517(15) Uani 1 1 d . . . O1 O 0.3661(2) 0.67597(19) 0.42745(16) 0.0304(5) Uani 1 1 d . . . O2 O 0.6299(2) 0.36406(19) 0.40104(16) 0.0301(5) Uani 1 1 d . . . O3 O 0.6230(2) 0.5930(2) 0.39207(16) 0.0309(5) Uani 1 1 d . . . O4 O 0.3681(2) 0.44638(19) 0.43669(16) 0.0301(5) Uani 1 1 d . . . O5 O 0.4882(2) 0.5355(2) 0.23739(16) 0.0326(5) Uani 1 1 d . . . O6 O 1.0701(3) 0.3127(3) 0.0329(2) 0.0664(9) Uani 1 1 d . . . O7 O 0.0767(3) 0.3929(3) 0.3405(2) 0.0554(7) Uani 1 1 d . . . O8 O -0.0596(3) 0.3719(3) 0.4662(2) 0.0606(8) Uani 1 1 d . . . O9 O 0.0393(3) 0.2301(3) 0.3789(3) 0.0729(11) Uani 1 1 d . . . N1 N 0.2078(2) 0.2978(2) 0.6376(2) 0.0291(5) Uani 1 1 d . . . N2 N 0.2186(2) 0.1941(2) 0.7883(2) 0.0294(5) Uani 1 1 d . . . N3 N 0.8398(2) 0.0040(2) 0.7112(2) 0.0307(6) Uani 1 1 d . . . N4 N 0.8258(2) 0.1140(2) 0.5627(2) 0.0300(6) Uani 1 1 d . . . N5 N 0.2970(3) 0.5629(3) 0.1892(2) 0.0356(6) Uani 1 1 d . . . N6 N 0.8887(3) 0.3797(4) 0.1346(3) 0.0573(10) Uani 1 1 d . . . N7 N 0.0185(3) 0.3321(3) 0.3955(2) 0.0380(6) Uani 1 1 d . . . C1 C 0.3373(3) 0.4048(3) 0.5268(2) 0.0270(6) Uani 1 1 d . . . C2 C 0.2439(3) 0.3431(3) 0.5328(2) 0.0310(7) Uani 1 1 d . . . H2A H 0.1693 0.3987 0.5019 0.037 Uiso 1 1 calc R . . H2B H 0.2807 0.2777 0.4935 0.037 Uiso 1 1 calc R . . C3 C 0.0909(3) 0.3354(4) 0.6882(3) 0.0547(11) Uani 1 1 d . . . H3 H 0.0197 0.3947 0.6627 0.066 Uiso 1 1 calc R . . C4 C 0.0978(3) 0.2704(4) 0.7822(3) 0.0575(12) Uani 1 1 d . . . H4 H 0.0320 0.2765 0.8337 0.069 Uiso 1 1 calc R . . C5 C 0.2831(3) 0.2122(3) 0.6998(3) 0.0366(7) Uani 1 1 d . . . H5 H 0.3680 0.1714 0.6836 0.044 Uiso 1 1 calc R . . C6 C 0.2659(3) 0.1092(3) 0.8805(3) 0.0355(7) Uani 1 1 d . . . H6A H 0.2316 0.0465 0.8915 0.043 Uiso 1 1 calc R . . H6B H 0.2387 0.1496 0.9402 0.043 Uiso 1 1 calc R . . C7 C 0.4075(3) 0.0561(3) 0.8675(2) 0.0313(7) Uani 1 1 d . . . C8 C 0.4665(3) -0.0452(3) 0.8182(2) 0.0302(6) Uani 1 1 d . . . C9 C 0.3968(4) -0.1031(3) 0.7830(3) 0.0400(8) Uani 1 1 d . . . H9 H 0.3097 -0.0735 0.7937 0.048 Uiso 1 1 calc R . . C10 C 0.4543(4) -0.1990(4) 0.7348(3) 0.0447(9) Uani 1 1 d . . . H10 H 0.4069 -0.2350 0.7132 0.054 Uiso 1 1 calc R . . C11 C 0.5876(4) -0.2451(3) 0.7170(3) 0.0445(9) Uani 1 1 d . . . H11 H 0.6268 -0.3113 0.6839 0.053 Uiso 1 1 calc R . . C12 C 0.6576(3) -0.1939(3) 0.7475(3) 0.0381(8) Uani 1 1 d . . . H12 H 0.7445 -0.2253 0.7344 0.046 Uiso 1 1 calc R . . C13 C 0.6016(3) -0.0919(3) 0.8000(2) 0.0316(7) Uani 1 1 d . . . C14 C 0.6724(3) -0.0360(3) 0.8309(2) 0.0309(7) Uani 1 1 d . . . C15 C 0.6132(3) 0.0643(3) 0.8808(2) 0.0321(7) Uani 1 1 d . . . C16 C 0.6832(4) 0.1218(3) 0.9148(3) 0.0394(8) Uani 1 1 d . . . H16 H 0.7703 0.0918 0.9042 0.047 Uiso 1 1 calc R . . C17 C 0.6253(4) 0.2195(4) 0.9622(3) 0.0478(9) Uani 1 1 d . . . H17 H 0.6728 0.2544 0.9851 0.057 Uiso 1 1 calc R . . C18 C 0.4941(4) 0.2673(3) 0.9766(3) 0.0467(9) Uani 1 1 d . . . H18 H 0.4555 0.3352 1.0077 0.056 Uiso 1 1 calc R . . C19 C 0.4217(4) 0.2173(3) 0.9465(3) 0.0409(8) Uani 1 1 d . . . H19 H 0.3347 0.2513 0.9570 0.049 Uiso 1 1 calc R . . C20 C 0.4780(3) 0.1125(3) 0.8986(2) 0.0310(7) Uani 1 1 d . . . C21 C 0.8121(3) -0.0760(3) 0.8027(3) 0.0357(7) Uani 1 1 d . . . H21A H 0.8535 -0.0744 0.8596 0.043 Uiso 1 1 calc R . . H21B H 0.8434 -0.1568 0.7879 0.043 Uiso 1 1 calc R . . C22 C 0.9393(3) 0.0435(3) 0.6932(3) 0.0375(8) Uani 1 1 d . . . H22 H 1.0011 0.0260 0.7367 0.045 Uiso 1 1 calc R . . C23 C 0.9303(3) 0.1119(3) 0.6012(3) 0.0372(7) Uani 1 1 d . . . H23 H 0.9846 0.1508 0.5692 0.045 Uiso 1 1 calc R . . C24 C 0.7725(3) 0.0477(3) 0.6313(3) 0.0335(7) Uani 1 1 d . . . H24 H 0.7004 0.0344 0.6243 0.040 Uiso 1 1 calc R . . C25 C 0.7748(3) 0.1822(3) 0.4676(2) 0.0319(7) Uani 1 1 d . . . H25A H 0.7420 0.1358 0.4373 0.038 Uiso 1 1 calc R . . H25B H 0.8421 0.1968 0.4199 0.038 Uiso 1 1 calc R . . C26 C 0.6705(3) 0.3010(3) 0.4827(2) 0.0267(6) Uani 1 1 d . . . C27 C 0.4209(3) 0.5140(3) 0.1872(2) 0.0333(7) Uani 1 1 d . . . H27 H 0.4612 0.4578 0.1435 0.040 Uiso 1 1 calc R . . C28 C 0.2253(4) 0.5249(4) 0.1324(4) 0.0545(10) Uani 1 1 d . . . H28A H 0.2819 0.4716 0.0875 0.082 Uiso 1 1 calc R . . H28B H 0.1701 0.5929 0.0927 0.082 Uiso 1 1 calc R . . H28C H 0.1769 0.4850 0.1796 0.082 Uiso 1 1 calc R . . C29 C 0.2262(3) 0.6533(4) 0.2538(3) 0.0423(8) Uani 1 1 d . . . H29A H 0.1888 0.6182 0.3147 0.063 Uiso 1 1 calc R . . H29B H 0.1615 0.7150 0.2169 0.063 Uiso 1 1 calc R . . H29C H 0.2815 0.6862 0.2723 0.063 Uiso 1 1 calc R . . C30 C 0.8163(7) 0.4783(6) 0.1951(6) 0.100(2) Uani 1 1 d . . . H30A H 0.8603 0.5322 0.1870 0.150 Uiso 1 1 calc R . . H30B H 0.8070 0.4463 0.2663 0.150 Uiso 1 1 calc R . . H30C H 0.7349 0.5197 0.1709 0.150 Uiso 1 1 calc R . . C32 C 0.9960(5) 0.3836(6) 0.0837(4) 0.0759(15) Uani 1 1 d . . . H32 H 1.0159 0.4490 0.0878 0.091 Uiso 1 1 calc R . . C31 C 0.8356(9) 0.2911(7) 0.1507(5) 0.111(3) Uani 1 1 d . . . H31A H 0.7562 0.3167 0.1912 0.166 Uiso 1 1 calc R . . H31B H 0.8910 0.2191 0.1860 0.166 Uiso 1 1 calc R . . H31C H 0.8233 0.2770 0.0857 0.166 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 0.0272(2) 0.0246(2) 0.0234(2) -0.00247(17) -0.00336(17) -0.00914(18) O1 0.0329(11) 0.0270(11) 0.0280(11) -0.0047(8) -0.0034(9) -0.0064(9) O2 0.0314(11) 0.0295(11) 0.0266(11) -0.0028(9) -0.0036(8) -0.0083(9) O3 0.0339(11) 0.0333(12) 0.0280(11) -0.0027(9) -0.0043(9) -0.0153(9) O4 0.0337(11) 0.0316(11) 0.0268(11) -0.0029(9) -0.0029(9) -0.0143(9) O5 0.0315(11) 0.0419(13) 0.0232(10) -0.0020(9) -0.0035(8) -0.0128(10) O6 0.0567(19) 0.063(2) 0.0550(18) -0.0115(15) 0.0118(15) 0.0011(16) O7 0.0490(16) 0.0511(17) 0.0640(19) 0.0058(14) -0.0040(13) -0.0232(14) O8 0.070(2) 0.0506(17) 0.0531(17) -0.0184(14) 0.0160(15) -0.0158(15) O9 0.073(2) 0.0545(19) 0.093(3) -0.0351(18) 0.0406(19) -0.0325(17) N1 0.0251(12) 0.0313(14) 0.0306(13) -0.0004(10) -0.0040(10) -0.0113(11) N2 0.0250(12) 0.0300(13) 0.0300(13) -0.0011(11) -0.0014(10) -0.0085(11) N3 0.0260(13) 0.0302(14) 0.0327(14) -0.0012(11) -0.0038(10) -0.0078(11) N4 0.0282(13) 0.0268(13) 0.0313(14) -0.0009(10) -0.0026(10) -0.0075(11) N5 0.0293(14) 0.0441(16) 0.0339(14) -0.0056(12) -0.0056(11) -0.0128(12) N6 0.0297(16) 0.078(3) 0.048(2) 0.0091(18) -0.0003(14) -0.0119(16) N7 0.0341(15) 0.0383(16) 0.0409(16) -0.0026(13) -0.0054(12) -0.0132(13) C1 0.0247(14) 0.0240(14) 0.0296(15) -0.0046(12) -0.0028(11) -0.0054(12) C2 0.0293(15) 0.0335(16) 0.0296(16) 0.0009(13) -0.0058(12) -0.0120(13) C3 0.0246(17) 0.070(3) 0.047(2) 0.0123(19) 0.0009(15) -0.0029(17) C4 0.0217(16) 0.078(3) 0.046(2) 0.016(2) 0.0026(15) -0.0016(18) C5 0.0298(16) 0.0409(19) 0.0302(17) 0.0020(14) -0.0003(13) -0.0073(14) C6 0.0325(17) 0.0389(18) 0.0295(16) 0.0022(14) 0.0000(13) -0.0115(14) C7 0.0320(16) 0.0325(16) 0.0238(15) 0.0027(12) -0.0030(12) -0.0085(13) C8 0.0327(16) 0.0330(16) 0.0248(15) 0.0006(12) -0.0042(12) -0.0134(13) C9 0.045(2) 0.045(2) 0.0336(17) -0.0012(15) -0.0079(14) -0.0204(17) C10 0.062(2) 0.050(2) 0.0350(18) -0.0030(16) -0.0099(17) -0.0331(19) C11 0.065(2) 0.040(2) 0.0310(18) -0.0079(15) 0.0056(16) -0.0236(18) C12 0.0401(18) 0.0332(17) 0.0366(18) -0.0058(14) 0.0057(14) -0.0114(15) C13 0.0346(16) 0.0318(16) 0.0252(15) 0.0020(12) -0.0025(12) -0.0115(13) C14 0.0328(16) 0.0299(16) 0.0259(15) 0.0048(12) -0.0041(12) -0.0105(13) C15 0.0380(17) 0.0344(17) 0.0238(15) 0.0035(12) -0.0060(12) -0.0154(14) C16 0.048(2) 0.043(2) 0.0311(17) 0.0028(14) -0.0073(14) -0.0224(16) C17 0.077(3) 0.049(2) 0.0326(18) -0.0048(16) -0.0061(17) -0.041(2) C18 0.070(3) 0.037(2) 0.0355(19) -0.0130(15) 0.0050(17) -0.0220(19) C19 0.053(2) 0.0331(18) 0.0303(17) -0.0031(14) 0.0021(15) -0.0124(16) C20 0.0401(17) 0.0290(16) 0.0207(14) 0.0018(12) -0.0028(12) -0.0114(13) C21 0.0338(17) 0.0343(17) 0.0344(17) 0.0053(14) -0.0056(13) -0.0112(14) C22 0.0276(16) 0.0387(18) 0.046(2) 0.0001(15) -0.0095(14) -0.0128(14) C23 0.0297(16) 0.0408(19) 0.0427(19) -0.0003(15) -0.0046(14) -0.0169(14) C24 0.0276(15) 0.0347(17) 0.0356(17) 0.0005(13) -0.0054(13) -0.0101(13) C25 0.0322(16) 0.0315(16) 0.0272(15) -0.0031(12) -0.0014(12) -0.0072(13) C26 0.0263(14) 0.0262(15) 0.0291(15) -0.0032(12) -0.0019(12) -0.0117(12) C27 0.0327(16) 0.0406(18) 0.0252(15) -0.0037(13) -0.0054(12) -0.0111(14) C28 0.039(2) 0.068(3) 0.063(3) -0.023(2) -0.0124(18) -0.017(2) C29 0.0315(17) 0.053(2) 0.0378(19) -0.0089(16) -0.0046(14) -0.0088(16) C30 0.117(5) 0.086(4) 0.100(5) -0.028(4) -0.036(4) -0.021(4) C32 0.067(3) 0.087(4) 0.067(3) 0.010(3) -0.013(3) -0.027(3) C31 0.190(8) 0.116(6) 0.068(4) -0.008(4) -0.002(4) -0.108(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 Cu1 O3 1.961(2) . ? Cu1 O4 1.973(2) . ? Cu1 O2 1.979(2) . ? Cu1 O1 1.981(2) . ? Cu1 O5 2.144(2) . ? Cu1 Cu1 2.6614(8) 2_666 ? O1 C26 1.257(4) 2_666 ? O2 C26 1.253(4) . ? O3 C1 1.253(4) 2_666 ? O4 C1 1.261(4) . ? O5 C27 1.233(4) . ? O6 C32 1.199(7) . ? O7 N7 1.246(4) . ? O8 N7 1.232(4) . ? O9 N7 1.243(4) . ? N1 C5 1.324(4) . ? N1 C3 1.361(4) . ? N1 C2 1.457(4) . ? N2 C5 1.318(4) . ? N2 C4 1.362(4) . ? N2 C6 1.479(4) . ? N3 C24 1.328(4) . ? N3 C22 1.379(4) . ? N3 C21 1.484(4) . ? N4 C24 1.335(4) . ? N4 C23 1.378(4) . ? N4 C25 1.454(4) . ? N5 C27 1.325(4) . ? N5 C29 1.453(5) . ? N5 C28 1.457(5) . ? N6 C32 1.326(6) . ? N6 C31 1.408(7) . ? N6 C30 1.492(8) . ? C1 O3 1.253(4) 2_666 ? C1 C2 1.522(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.345(5) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.510(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C20 1.404(5) . ? C7 C8 1.411(5) . ? C8 C9 1.437(5) . ? C8 C13 1.443(5) . ? C9 C10 1.349(6) . ? C9 H9 0.9300 . ? C10 C11 1.424(6) . ? C10 H10 0.9300 . ? C11 C12 1.346(5) . ? C11 H11 0.9300 . ? C12 C13 1.440(5) . ? C12 H12 0.9300 . ? C13 C14 1.401(5) . ? C14 C15 1.405(5) . ? C14 C21 1.506(4) . ? C15 C16 1.429(5) . ? C15 C20 1.444(5) . ? C16 C17 1.360(6) . ? C16 H16 0.9300 . ? C17 C18 1.400(6) . ? C17 H17 0.9300 . ? C18 C19 1.357(6) . ? C18 H18 0.9300 . ? C19 C20 1.433(5) . ? C19 H19 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.340(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.529(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 O1 1.257(4) 2_666 ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C32 H32 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 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 O3 Cu1 O4 168.10(9) . . ? O3 Cu1 O2 89.26(9) . . ? O4 Cu1 O2 90.07(9) . . ? O3 Cu1 O1 88.20(9) . . ? O4 Cu1 O1 89.99(9) . . ? O2 Cu1 O1 167.92(9) . . ? O3 Cu1 O5 98.38(9) . . ? O4 Cu1 O5 93.50(9) . . ? O2 Cu1 O5 90.91(9) . . ? O1 Cu1 O5 101.14(9) . . ? O3 Cu1 Cu1 86.69(7) . 2_666 ? O4 Cu1 Cu1 81.42(6) . 2_666 ? O2 Cu1 Cu1 83.98(6) . 2_666 ? O1 Cu1 Cu1 84.09(6) . 2_666 ? O5 Cu1 Cu1 172.77(7) . 2_666 ? C26 O1 Cu1 122.0(2) 2_666 . ? C26 O2 Cu1 122.3(2) . . ? C1 O3 Cu1 119.5(2) 2_666 . ? C1 O4 Cu1 124.9(2) . . ? C27 O5 Cu1 132.9(2) . . ? C5 N1 C3 108.3(3) . . ? C5 N1 C2 125.8(3) . . ? C3 N1 C2 125.9(3) . . ? C5 N2 C4 107.9(3) . . ? C5 N2 C6 127.5(3) . . ? C4 N2 C6 124.6(3) . . ? C24 N3 C22 108.7(3) . . ? C24 N3 C21 124.7(3) . . ? C22 N3 C21 126.6(3) . . ? C24 N4 C23 108.3(3) . . ? C24 N4 C25 124.6(3) . . ? C23 N4 C25 127.0(3) . . ? C27 N5 C29 120.6(3) . . ? C27 N5 C28 122.3(3) . . ? C29 N5 C28 117.1(3) . . ? C32 N6 C31 130.8(6) . . ? C32 N6 C30 116.3(5) . . ? C31 N6 C30 112.5(5) . . ? O8 N7 O9 119.6(3) . . ? O8 N7 O7 120.6(3) . . ? O9 N7 O7 119.8(3) . . ? O3 C1 O4 127.4(3) 2_666 . ? O3 C1 C2 118.8(3) 2_666 . ? O4 C1 C2 113.7(3) . . ? N1 C2 C1 112.8(3) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 N1 106.9(3) . . ? C4 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? C3 C4 N2 107.7(3) . . ? C3 C4 H4 126.2 . . ? N2 C4 H4 126.2 . . ? N2 C5 N1 109.3(3) . . ? N2 C5 H5 125.4 . . ? N1 C5 H5 125.4 . . ? N2 C6 C7 110.2(2) . . ? N2 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C20 C7 C8 121.1(3) . . ? C20 C7 C6 119.6(3) . . ? C8 C7 C6 119.2(3) . . ? C7 C8 C9 122.5(3) . . ? C7 C8 C13 119.3(3) . . ? C9 C8 C13 118.2(3) . . ? C10 C9 C8 121.9(4) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.9(4) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 122.8(3) . . ? C14 C13 C8 119.8(3) . . ? C12 C13 C8 117.5(3) . . ? C13 C14 C15 120.6(3) . . ? C13 C14 C21 120.2(3) . . ? C15 C14 C21 118.9(3) . . ? C14 C15 C16 121.8(3) . . ? C14 C15 C20 120.1(3) . . ? C16 C15 C20 118.1(3) . . ? C17 C16 C15 121.6(4) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 119.9(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 121.7(4) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 120.6(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C7 C20 C19 122.9(3) . . ? C7 C20 C15 119.0(3) . . ? C19 C20 C15 118.1(3) . . ? N3 C21 C14 109.3(3) . . ? N3 C21 H21A 109.8 . . ? C14 C21 H21A 109.8 . . ? N3 C21 H21B 109.8 . . ? C14 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? C23 C22 N3 107.2(3) . . ? C23 C22 H22 126.4 . . ? N3 C22 H22 126.4 . . ? C22 C23 N4 107.5(3) . . ? C22 C23 H23 126.3 . . ? N4 C23 H23 126.3 . . ? N3 C24 N4 108.4(3) . . ? N3 C24 H24 125.8 . . ? N4 C24 H24 125.8 . . ? N4 C25 C26 113.0(3) . . ? N4 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? N4 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? O2 C26 O1 127.5(3) . 2_666 ? O2 C26 C25 114.1(3) . . ? O1 C26 C25 118.4(3) 2_666 . ? O5 C27 N5 126.7(3) . . ? O5 C27 H27 116.7 . . ? N5 C27 H27 116.7 . . ? N5 C28 H28A 109.5 . . ? N5 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N5 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C29 H29A 109.5 . . ? N5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N6 C30 H30A 109.5 . . ? N6 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N6 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O6 C32 N6 127.5(6) . . ? O6 C32 H32 116.2 . . ? N6 C32 H32 116.2 . . ? N6 C31 H31A 109.5 . . ? N6 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N6 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 55 33 ' ' 2 0.500 0.000 0.500 87 42 ' ' _platon_squeeze_details ; Approximately 8.3% of the unit cell volume comprises two disordered solvents which could not be modelled as discrete atomic sites. We employed PLATON SQUEEZE to calculate the contribution to the diffraction from the solvent region. SQUEEZE estimated a total count of 75 electrons per unit cell, which was assigned to be two nitrate ions per unit cell. The final formula was calculated based on the elemental analysis data. ; _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 70.84 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.434 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 924621' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Br0.50 Cu N4 O6' _chemical_formula_weight 594.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.5328(5) _cell_length_b 11.3109(12) _cell_length_c 13.2988(14) _cell_angle_alpha 77.560(9) _cell_angle_beta 82.903(9) _cell_angle_gamma 84.026(9) _cell_volume 658.61(12) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4147 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 70.78 _exptl_crystal_description Rectangle _exptl_crystal_colour 'light green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 305 _exptl_absorpt_coefficient_mu 2.466 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.0877 _exptl_absorpt_correction_T_max 0.7639 _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4147 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_unetI/netI 0.0404 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 70.78 _reflns_number_total 2429 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997); Diamond 3.2i (Brandenburg,1999) ; _computing_publication_material 'MERCURY (Macrae et al., 2006)' _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^)+(0.1160P)^2^+2.9114P] 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 2429 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.2201 _refine_ls_wR_factor_gt 0.2095 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Br1 Br 0.0000 0.0000 0.5000 0.0195(3) Uani 0.50 2 d SP . . Cu1 Cu 1.0000 0.0000 0.0000 0.0345(4) Uani 1 2 d S . . O1 O 0.8433(10) -0.1599(4) 0.0164(3) 0.0407(9) Uani 1 1 d . . . H1A H 0.6579 -0.1770 -0.0075 0.061 Uiso 1 1 d R . . H1B H 0.9330 -0.2397 0.0499 0.061 Uiso 1 1 d R . . O2 O 0.7262(8) 0.0471(3) 0.1134(3) 0.0348(9) Uani 1 1 d . . . O3 O 0.3641(9) -0.0793(3) 0.1244(3) 0.0372(9) Uani 1 1 d . . . N1 N 0.4149(10) 0.1721(4) 0.2479(4) 0.0328(10) Uani 1 1 d . . . N2 N 0.6576(10) 0.2799(4) 0.3209(3) 0.0300(9) Uani 1 1 d . . . C1 C 0.4751(11) 0.0058(5) 0.1482(4) 0.0306(11) Uani 1 1 d . . . C2 C 0.2818(12) 0.0680(5) 0.2284(4) 0.0361(12) Uani 1 1 d . . . H2A H 0.0881 0.0949 0.2040 0.043 Uiso 1 1 calc R . . H2B H 0.2512 0.0092 0.2929 0.043 Uiso 1 1 calc R . . C3 C 0.4197(13) 0.2855(6) 0.1846(5) 0.0398(13) Uani 1 1 d . . . H3 H 0.3341 0.3112 0.1227 0.048 Uiso 1 1 calc R . . C4 C 0.5743(14) 0.3529(5) 0.2303(5) 0.0401(13) Uani 1 1 d . . . H4 H 0.6157 0.4334 0.2050 0.048 Uiso 1 1 calc R . . C5 C 0.5578(11) 0.1692(5) 0.3305(4) 0.0295(11) Uani 1 1 d . . . H5 H 0.5838 0.1030 0.3848 0.035 Uiso 1 1 calc R . . C6 C 0.8291(12) 0.3140(5) 0.3975(4) 0.0310(11) Uani 1 1 d . . . H6A H 1.0163 0.3436 0.3628 0.037 Uiso 1 1 calc R . . H6B H 0.8746 0.2426 0.4500 0.037 Uiso 1 1 calc R . . C7 C 0.6564(11) 0.4110(5) 0.4488(4) 0.0289(11) Uani 1 1 d . . . C8 C 0.4471(11) 0.3755(4) 0.5355(4) 0.0279(10) Uani 1 1 d . . . C9 C 0.3874(13) 0.2517(5) 0.5735(4) 0.0344(12) Uani 1 1 d . . . H9 H 0.4900 0.1921 0.5412 0.041 Uiso 1 1 calc R . . C10 C 0.1812(13) 0.2186(5) 0.6570(4) 0.0359(12) Uani 1 1 d . . . H10 H 0.1433 0.1374 0.6799 0.043 Uiso 1 1 calc R . . C11 C 0.0266(13) 0.3070(5) 0.7083(4) 0.0388(13) Uani 1 1 d . . . H11 H -0.1106 0.2837 0.7655 0.047 Uiso 1 1 calc R . . C12 C 0.0774(12) 0.4263(5) 0.6746(4) 0.0349(12) Uani 1 1 d . . . H12 H -0.0273 0.4832 0.7094 0.042 Uiso 1 1 calc R . . C13 C 0.7130(12) 0.5331(5) 0.4128(4) 0.0290(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0263(7) 0.0130(6) 0.0189(6) -0.0034(4) -0.0014(5) -0.0011(5) Cu1 0.0363(7) 0.0324(6) 0.0366(7) -0.0131(5) 0.0042(5) -0.0079(5) O1 0.048(2) 0.035(2) 0.042(2) -0.0135(17) 0.0052(18) -0.0152(17) O2 0.034(2) 0.034(2) 0.038(2) -0.0144(16) 0.0041(16) -0.0076(15) O3 0.042(2) 0.035(2) 0.039(2) -0.0143(17) 0.0001(17) -0.0097(16) N1 0.030(2) 0.035(2) 0.035(2) -0.0144(19) 0.0015(18) -0.0030(18) N2 0.034(2) 0.029(2) 0.029(2) -0.0104(17) -0.0004(18) -0.0029(17) C1 0.031(3) 0.035(3) 0.025(2) -0.005(2) 0.001(2) -0.010(2) C2 0.032(3) 0.044(3) 0.037(3) -0.017(2) 0.003(2) -0.011(2) C3 0.043(3) 0.044(3) 0.033(3) -0.010(2) -0.004(2) -0.001(3) C4 0.053(4) 0.032(3) 0.037(3) -0.010(2) -0.002(3) -0.007(2) C5 0.029(2) 0.032(3) 0.030(3) -0.013(2) 0.001(2) -0.003(2) C6 0.032(3) 0.031(3) 0.033(3) -0.012(2) -0.003(2) -0.007(2) C7 0.032(3) 0.029(3) 0.028(2) -0.009(2) -0.006(2) -0.003(2) C8 0.034(3) 0.023(2) 0.029(2) -0.0073(19) -0.006(2) -0.0034(19) C9 0.040(3) 0.029(3) 0.036(3) -0.011(2) -0.002(2) -0.006(2) C10 0.046(3) 0.030(3) 0.033(3) -0.003(2) -0.005(2) -0.013(2) C11 0.044(3) 0.039(3) 0.034(3) -0.006(2) 0.001(2) -0.012(2) C12 0.038(3) 0.033(3) 0.037(3) -0.015(2) -0.001(2) -0.005(2) C13 0.033(3) 0.028(3) 0.029(2) -0.008(2) -0.006(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.961(4) . ? Cu1 O2 1.961(4) 2_755 ? Cu1 O1 1.970(4) 2_755 ? Cu1 O1 1.970(4) . ? O1 H1A 0.9848 . ? O1 H1B 0.9867 . ? O2 C1 1.271(6) . ? O3 C1 1.246(6) . ? N1 C5 1.335(7) . ? N1 C3 1.375(8) . ? N1 C2 1.462(7) . ? N2 C5 1.350(7) . ? N2 C4 1.376(7) . ? N2 C6 1.489(6) . ? C1 C2 1.537(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.363(8) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.515(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C13 1.400(7) . ? C7 C8 1.414(7) . ? C8 C9 1.426(7) . ? C8 C13 1.448(7) 2_666 ? C9 C10 1.372(8) . ? C9 H9 0.9300 . ? C10 C11 1.409(8) . ? C10 H10 0.9300 . ? C11 C12 1.362(8) . ? C11 H11 0.9300 . ? C12 C13 1.433(8) 2_666 ? C12 H12 0.9300 . ? C13 C12 1.433(8) 2_666 ? C13 C8 1.448(7) 2_666 ? 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 Cu1 O2 180.0(3) . 2_755 ? O2 Cu1 O1 85.72(16) . 2_755 ? O2 Cu1 O1 94.28(16) 2_755 2_755 ? O2 Cu1 O1 94.28(16) . . ? O2 Cu1 O1 85.72(16) 2_755 . ? O1 Cu1 O1 180.0(2) 2_755 . ? Cu1 O1 H1A 127.1 . . ? Cu1 O1 H1B 127.6 . . ? H1A O1 H1B 105.3 . . ? C1 O2 Cu1 126.4(3) . . ? C5 N1 C3 109.7(5) . . ? C5 N1 C2 124.1(5) . . ? C3 N1 C2 126.1(5) . . ? C5 N2 C4 108.8(4) . . ? C5 N2 C6 124.2(4) . . ? C4 N2 C6 127.0(4) . . ? O3 C1 O2 127.5(5) . . ? O3 C1 C2 115.5(5) . . ? O2 C1 C2 116.9(5) . . ? N1 C2 C1 112.9(4) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 N1 106.6(5) . . ? C4 C3 H3 126.7 . . ? N1 C3 H3 126.7 . . ? C3 C4 N2 107.3(5) . . ? C3 C4 H4 126.3 . . ? N2 C4 H4 126.3 . . ? N1 C5 N2 107.5(5) . . ? N1 C5 H5 126.2 . . ? N2 C5 H5 126.2 . . ? N2 C6 C7 111.6(4) . . ? N2 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C13 C7 C8 121.0(5) . . ? C13 C7 C6 120.1(5) . . ? C8 C7 C6 118.9(5) . . ? C7 C8 C9 121.8(5) . . ? C7 C8 C13 119.5(5) . 2_666 ? C9 C8 C13 118.7(5) . 2_666 ? C10 C9 C8 121.2(5) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.4(5) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.3(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 122.1(5) . 2_666 ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 2_666 . ? C7 C13 C12 123.2(5) . 2_666 ? C7 C13 C8 119.5(5) . 2_666 ? C12 C13 C8 117.3(5) 2_666 2_666 ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 67.70 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 2.087 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.149 _database_code_depnum_ccdc_archive 'CCDC 924622' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Br0.50 N2 O3 Zn0.50' _chemical_formula_weight 317.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.5284(4) _cell_length_b 11.4135(9) _cell_length_c 13.2801(11) _cell_angle_alpha 78.119(7) _cell_angle_beta 83.978(7) _cell_angle_gamma 84.959(7) _cell_volume 666.42(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4525 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 70.78 _exptl_crystal_description Rectangle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 323 _exptl_absorpt_coefficient_mu 3.445 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.0805 _exptl_absorpt_correction_T_max 0.1768 _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby Oxford Diffraction (2007). Oxford Diffraction Ltd., Xcalibur CCD system ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4525 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_unetI/netI 0.0499 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 70.78 _reflns_number_total 2505 _reflns_number_gt 2055 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997); Diamond 3.2i (Brandenburg,1999) ; _computing_publication_material 'MERCURY (Macrae et al., 2006)' _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^)+(0.1022P)^2^+2.7809P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2505 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.2115 _refine_ls_wR_factor_gt 0.1991 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 Br1 Br 0.5000 0.0000 0.5000 0.0397(3) Uani 1 2 d S . . Zn1 Zn 0.5000 0.0000 0.0000 0.0355(4) Uani 1 2 d S . . O1 O 0.2114(9) 0.0478(4) 0.1171(3) 0.0382(10) Uani 1 1 d . . . O2 O 0.8286(9) -0.0622(4) 0.1102(4) 0.0371(10) Uani 1 1 d . . . O3 O 0.3412(12) -0.1708(4) 0.0204(4) 0.0457(11) Uani 1 1 d . . . H3A H 0.1817 -0.1772 0.0638 0.069 Uiso 1 1 d R . . H3B H 0.4753 -0.2263 0.0449 0.069 Uiso 1 1 d R . . N1 N 0.8973(11) 0.1759(5) 0.2467(4) 0.0350(11) Uani 1 1 d . . . N2 N 1.1485(11) 0.2810(4) 0.3206(4) 0.0315(10) Uani 1 1 d . . . C1 C 0.9510(13) 0.0145(6) 0.1433(5) 0.0348(13) Uani 1 1 d . . . C2 C 0.7609(14) 0.0736(6) 0.2249(5) 0.0374(13) Uani 1 1 d . . . H2A H 0.5669 0.1002 0.2006 0.045 Uiso 1 1 calc R . . H2B H 0.7319 0.0145 0.2883 0.045 Uiso 1 1 calc R . . C3 C 0.9030(16) 0.2883(6) 0.1845(5) 0.0424(15) Uani 1 1 d . . . H3 H 0.8155 0.3139 0.1227 0.051 Uiso 1 1 calc R . . C4 C 1.0605(15) 0.3543(6) 0.2308(5) 0.0411(14) Uani 1 1 d . . . H4 H 1.1019 0.4342 0.2067 0.049 Uiso 1 1 calc R . . C5 C 1.0457(13) 0.1747(6) 0.3285(5) 0.0344(13) Uani 1 1 d . . . H5 H 1.0724 0.1094 0.3824 0.041 Uiso 1 1 calc R . . C6 C 1.3234(13) 0.3170(5) 0.3957(5) 0.0334(13) Uani 1 1 d . . . H6A H 1.5060 0.3488 0.3599 0.040 Uiso 1 1 calc R . . H6B H 1.3770 0.2467 0.4468 0.040 Uiso 1 1 calc R . . C7 C 1.1550(13) 0.4110(6) 0.4504(5) 0.0358(13) Uani 1 1 d . . . C8 C 0.9506(14) 0.3751(6) 0.5351(5) 0.0377(13) Uani 1 1 d . . . C9 C 0.8930(15) 0.2540(6) 0.5750(5) 0.0398(14) Uani 1 1 d . . . H9 H 0.9958 0.1950 0.5435 0.048 Uiso 1 1 calc R . . C10 C 0.6956(16) 0.2205(6) 0.6565(5) 0.0430(15) Uani 1 1 d . . . H10 H 0.6612 0.1398 0.6793 0.052 Uiso 1 1 calc R . . C11 C 0.5380(15) 0.3083(6) 0.7085(5) 0.0412(14) Uani 1 1 d . . . H11 H 0.4024 0.2849 0.7652 0.049 Uiso 1 1 calc R . . C12 C 0.5871(15) 0.4245(7) 0.6749(6) 0.0443(15) Uani 1 1 d . . . H12 H 0.4833 0.4807 0.7095 0.053 Uiso 1 1 calc R . . C13 C 1.2060(14) 0.5342(6) 0.4124(5) 0.0383(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0409(5) 0.0394(5) 0.0391(5) -0.0083(4) -0.0052(4) -0.0012(4) Zn1 0.0315(6) 0.0395(7) 0.0380(7) -0.0139(5) -0.0015(5) -0.0032(5) O1 0.030(2) 0.047(2) 0.040(2) -0.0164(19) -0.0006(17) -0.0038(18) O2 0.028(2) 0.041(2) 0.045(3) -0.0147(19) -0.0036(18) -0.0052(17) O3 0.051(3) 0.044(3) 0.043(3) -0.007(2) -0.005(2) -0.015(2) N1 0.033(2) 0.037(3) 0.038(3) -0.014(2) -0.003(2) -0.003(2) N2 0.036(2) 0.031(2) 0.031(2) -0.015(2) -0.005(2) 0.0029(19) C1 0.028(3) 0.041(3) 0.035(3) -0.007(3) -0.001(2) -0.004(2) C2 0.038(3) 0.044(3) 0.034(3) -0.015(3) -0.002(2) -0.007(3) C3 0.049(4) 0.048(4) 0.030(3) -0.010(3) -0.003(3) 0.002(3) C4 0.047(4) 0.046(4) 0.032(3) -0.011(3) -0.005(3) -0.004(3) C5 0.027(3) 0.042(3) 0.038(3) -0.016(3) -0.003(2) 0.000(2) C6 0.036(3) 0.027(3) 0.042(3) -0.018(2) -0.008(3) 0.001(2) C7 0.031(3) 0.044(3) 0.035(3) -0.013(3) -0.007(2) 0.000(2) C8 0.033(3) 0.041(3) 0.040(3) -0.007(3) -0.011(3) -0.003(3) C9 0.041(3) 0.038(3) 0.045(4) -0.019(3) -0.008(3) 0.002(3) C10 0.050(4) 0.038(3) 0.042(4) -0.009(3) -0.007(3) -0.010(3) C11 0.041(3) 0.048(4) 0.036(3) -0.011(3) -0.002(3) -0.007(3) C12 0.038(3) 0.054(4) 0.042(4) -0.014(3) -0.001(3) -0.002(3) C13 0.033(3) 0.044(3) 0.041(3) -0.013(3) -0.008(2) -0.004(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 O1 2.055(4) . ? Zn1 O1 2.055(4) 2_655 ? Zn1 O3 2.092(5) . ? Zn1 O3 2.092(5) 2_655 ? Zn1 O2 2.169(4) 2_655 ? Zn1 O2 2.169(4) . ? O1 C1 1.263(7) 1_455 ? O2 C1 1.249(8) . ? O3 H3A 0.8734 . ? O3 H3B 0.8750 . ? N1 C5 1.333(8) . ? N1 C3 1.376(9) . ? N1 C2 1.460(8) . ? N2 C5 1.318(8) . ? N2 C4 1.382(8) . ? N2 C6 1.478(7) . ? C1 O1 1.263(7) 1_655 ? C1 C2 1.541(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.353(10) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.524(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.395(9) . ? C7 C13 1.423(10) . ? C8 C9 1.411(9) . ? C8 C13 1.459(9) 2_766 ? C9 C10 1.344(10) . ? C9 H9 0.9300 . ? C10 C11 1.430(10) . ? C10 H10 0.9300 . ? C11 C12 1.340(10) . ? C11 H11 0.9300 . ? C12 C13 1.439(10) 2_766 ? C12 H12 0.9300 . ? C13 C12 1.439(10) 2_766 ? C13 C8 1.459(9) 2_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 180.0(3) . 2_655 ? O1 Zn1 O3 93.47(19) . . ? O1 Zn1 O3 86.53(19) 2_655 . ? O1 Zn1 O3 86.53(19) . 2_655 ? O1 Zn1 O3 93.47(19) 2_655 2_655 ? O3 Zn1 O3 180.0(3) . 2_655 ? O1 Zn1 O2 90.99(17) . 2_655 ? O1 Zn1 O2 89.01(17) 2_655 2_655 ? O3 Zn1 O2 87.55(18) . 2_655 ? O3 Zn1 O2 92.45(18) 2_655 2_655 ? O1 Zn1 O2 89.01(17) . . ? O1 Zn1 O2 90.99(17) 2_655 . ? O3 Zn1 O2 92.45(18) . . ? O3 Zn1 O2 87.55(18) 2_655 . ? O2 Zn1 O2 180.0(3) 2_655 . ? C1 O1 Zn1 126.4(4) 1_455 . ? C1 O2 Zn1 118.2(4) . . ? Zn1 O3 H3A 110.7 . . ? Zn1 O3 H3B 110.8 . . ? H3A O3 H3B 108.1 . . ? C5 N1 C3 108.7(5) . . ? C5 N1 C2 125.6(6) . . ? C3 N1 C2 125.7(6) . . ? C5 N2 C4 108.5(5) . . ? C5 N2 C6 126.0(5) . . ? C4 N2 C6 125.5(5) . . ? O2 C1 O1 127.0(6) . 1_655 ? O2 C1 C2 115.7(5) . . ? O1 C1 C2 117.3(5) 1_655 . ? N1 C2 C1 112.6(5) . . ? N1 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 N1 106.7(6) . . ? C4 C3 H3 126.7 . . ? N1 C3 H3 126.7 . . ? C3 C4 N2 107.2(6) . . ? C3 C4 H4 126.4 . . ? N2 C4 H4 126.4 . . ? N2 C5 N1 109.0(6) . . ? N2 C5 H5 125.5 . . ? N1 C5 H5 125.5 . . ? N2 C6 C7 112.8(5) . . ? N2 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N2 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C13 121.5(6) . . ? C8 C7 C6 119.6(6) . . ? C13 C7 C6 118.9(6) . . ? C7 C8 C9 123.2(6) . . ? C7 C8 C13 119.0(6) . 2_766 ? C9 C8 C13 117.7(6) . 2_766 ? C10 C9 C8 122.7(6) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C9 C10 C11 120.3(6) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.6(6) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 122.6(7) . 2_766 ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 2_766 . ? C7 C13 C12 123.5(6) . 2_766 ? C7 C13 C8 119.5(6) . 2_766 ? C12 C13 C8 117.0(6) 2_766 2_766 ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.098 0.500 0.500 66 39 ' ' _platon_squeeze_details ; Approximately 10% of the unit cell volume comprises a disordered solvent which could not be modelled as discrete atomic sites. We employed PLATON SQUEEZE to calculate the contribution to the diffraction from the solvent region and thereby produced a set of solvent-free diffraction intensities. The SQUEEZE estimated a total count of 39 electrons per unit cell, which was assigned to be a Br ion per unit cell. The final formula was calculated based on the elemental analysis data. ; _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 70.78 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.544 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.151 _database_code_depnum_ccdc_archive 'CCDC 924623'