# Electronic Supplementary Material (ESI) for CrystEngComm # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H28 B2 Cu2 F8 N4 O12' _chemical_formula_weight 781.13 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' B B 0.0090 0.0039 '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' F F 0.0727 0.0534 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 16.6263(3) _cell_length_b 12.7971(3) _cell_length_c 14.4678(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3078.29(11) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3145 _cell_measurement_theta_min 4.61 _cell_measurement_theta_max 73.36 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.236 _exptl_crystal_size_mid 0.183 _exptl_crystal_size_min 0.144 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 2.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.80811 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7668 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.61 _diffrn_reflns_theta_max 73.36 _reflns_number_total 3145 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+16.5702P] 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 3145 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1562 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 F5 F 0.1580(9) 0.8672(11) 0.9854(9) 0.095 Uiso 0.403(11) 1 d P . 1 O1W O 0.3392(5) 0.8247(8) 0.9871(6) 0.062(2) Uani 0.50 1 d P A 1 F3 F 0.0773(14) 0.787(2) 1.0138(19) 0.095 Uiso 0.238(15) 1 d P . 2 C1S C -0.6290(4) 0.7500 1.2245(5) 0.0342(15) Uani 1 2 d S . . H1S1 H -0.5969 0.7934 1.2664 0.051 Uiso 0.50 1 calc PR . . H1S2 H -0.6312 0.6783 1.2483 0.051 Uiso 0.50 1 calc PR . . H1S3 H -0.6837 0.7783 1.2205 0.051 Uiso 0.50 1 calc PR . . F10 F -0.0626(10) 0.7843(14) 0.8007(6) 0.204(12) Uani 0.50 1 d P . . C2S C -0.1439(9) 0.8558(12) 1.0409(11) 0.068(4) Uiso 0.50 1 d P B 5 H2S1 H -0.1808 0.9119 1.0589 0.102 Uiso 0.50 1 calc PR B 5 H2S2 H -0.1324 0.8609 0.9746 0.102 Uiso 0.50 1 calc PR B 5 H2S3 H -0.0936 0.8623 1.0758 0.102 Uiso 0.50 1 calc PR B 5 O3S O -0.0909(10) 0.8902(14) 0.9859(12) 0.132(5) Uiso 0.50 1 d P C 6 C3S C -0.0635(16) 0.961(2) 1.0653(18) 0.140(9) Uiso 0.50 1 d P C 6 H3S1 H -0.0346 1.0211 1.0402 0.210 Uiso 0.50 1 calc PR C 6 H3S2 H -0.0277 0.9212 1.1063 0.210 Uiso 0.50 1 calc PR C 6 H3S3 H -0.1105 0.9846 1.1001 0.210 Uiso 0.50 1 calc PR C 6 B2 B -0.0482(8) 0.7500 0.7152(11) 0.075(4) Uani 1 2 d S . . F8 F 0.0329(3) 0.7500 0.6957(5) 0.0835(19) Uani 1 2 d S . . F9 F -0.0813(2) 0.8358(4) 0.6698(4) 0.0884(15) Uani 1 1 d . . . B1 B 0.1495(10) 0.7500 0.9958(12) 0.097(5) Uani 1 2 d S . . F1 F 0.1829(6) 0.7500 1.0824(6) 0.119(3) Uani 1 2 d S . . Cu1 Cu -0.46651(5) 0.7500 1.11570(6) 0.0207(2) Uani 1 2 d S . . Cu2 Cu -0.30844(5) 0.7500 1.08798(6) 0.0205(2) Uani 1 2 d S . . O2 O -0.30959(17) 0.8574(3) 1.1843(2) 0.0290(7) Uani 1 1 d . . . O3 O -0.46728(17) 0.8576(2) 1.0180(2) 0.0278(7) Uani 1 1 d . . . O4 O -0.33380(18) 0.8565(3) 0.9953(2) 0.0308(7) Uani 1 1 d . . . O1 O -0.44330(17) 0.8583(3) 1.2085(2) 0.0312(7) Uani 1 1 d . . . O1S O -0.5933(3) 0.7500 1.1351(4) 0.0472(15) Uani 1 2 d S . . H1S H -0.6272 0.7500 1.0822 0.057 Uiso 1 2 calc SR . . O2S O -0.1826(3) 0.7500 1.0617(4) 0.0427(13) Uani 1 2 d S . . N2 N -0.2817(2) 1.0106(3) 1.3037(3) 0.0303(9) Uani 1 1 d . . . C4 C -0.2259(3) 0.9842(4) 1.3651(3) 0.0313(10) Uani 1 1 d . . . H4 H -0.2336 0.9392 1.4166 0.038 Uiso 1 1 calc R . . N1 N -0.3423(2) 0.9687(3) 0.8426(3) 0.0296(8) Uani 1 1 d . . . C2 C -0.4038(3) 0.8856(3) 0.9781(3) 0.0266(9) Uani 1 1 d . . . C1 C -0.3725(3) 0.8878(4) 1.2235(3) 0.0270(9) Uani 1 1 d . . . C3 C -0.4143(3) 0.9652(4) 0.9008(3) 0.0336(11) Uani 1 1 d . . . H3A H -0.4615 0.9462 0.8627 0.040 Uiso 1 1 calc R . . H3B H -0.4242 1.0352 0.9278 0.040 Uiso 1 1 calc R . . C7 C -0.3634(3) 0.9685(4) 1.3002(3) 0.0319(10) Uani 1 1 d . . . H7A H -0.4020 1.0263 1.2897 0.038 Uiso 1 1 calc R . . H7B H -0.3766 0.9357 1.3603 0.038 Uiso 1 1 calc R . . C5 C -0.3294(3) 0.9097(4) 0.7647(4) 0.0397(12) Uani 1 1 d . . . H5 H -0.3677 0.8669 0.7340 0.048 Uiso 1 1 calc R . . C6 C -0.2476(3) 1.0762(4) 1.2401(4) 0.0439(13) Uani 1 1 d . . . H6 H -0.2737 1.1062 1.1881 0.053 Uiso 1 1 calc R . . F7 F 0.1936(8) 0.7735(15) 0.9202(10) 0.095 Uiso 0.337(11) 1 d P . . F2 F 0.0696(18) 0.7500 0.956(3) 0.095 Uiso 0.266(18) 2 d SP . . F6 F 0.2125(13) 0.8232(18) 0.9651(16) 0.095 Uiso 0.266(12) 1 d P . . F4 F 0.092(3) 0.844(5) 0.987(4) 0.095 Uiso 0.119(13) 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 O1W 0.068(6) 0.073(6) 0.044(5) -0.006(4) -0.017(4) 0.026(5) C1S 0.029(3) 0.043(4) 0.030(4) 0.000 0.010(3) 0.000 F10 0.299(18) 0.26(3) 0.049(5) -0.018(8) 0.012(7) 0.22(2) B2 0.058(7) 0.070(8) 0.096(10) 0.000 0.014(7) 0.000 F8 0.046(3) 0.082(4) 0.123(6) 0.000 -0.015(3) 0.000 F9 0.056(2) 0.088(3) 0.121(4) -0.019(3) 0.021(2) 0.017(2) B1 0.076(10) 0.136(16) 0.079(11) 0.000 0.017(8) 0.000 F1 0.160(8) 0.110(6) 0.086(6) 0.000 0.015(5) 0.000 Cu1 0.0131(4) 0.0282(5) 0.0210(5) 0.000 0.0014(3) 0.000 Cu2 0.0136(4) 0.0266(5) 0.0213(5) 0.000 0.0004(3) 0.000 O2 0.0209(14) 0.0334(17) 0.0327(17) -0.0099(14) -0.0020(12) 0.0018(13) O3 0.0237(14) 0.0318(16) 0.0280(16) 0.0068(14) 0.0073(12) 0.0058(13) O4 0.0243(15) 0.0408(18) 0.0273(16) 0.0114(14) 0.0033(12) 0.0014(14) O1 0.0215(15) 0.0433(19) 0.0289(16) -0.0115(15) -0.0008(12) -0.0002(14) O1S 0.013(2) 0.097(5) 0.031(3) 0.000 0.0043(19) 0.000 O2S 0.014(2) 0.070(4) 0.044(3) 0.000 0.002(2) 0.000 N2 0.0284(19) 0.033(2) 0.030(2) -0.0082(17) -0.0089(16) 0.0048(16) C4 0.032(2) 0.033(2) 0.029(2) -0.008(2) -0.0063(19) 0.006(2) N1 0.0292(19) 0.031(2) 0.029(2) 0.0099(17) 0.0072(16) 0.0059(17) C2 0.024(2) 0.026(2) 0.029(2) -0.0018(19) 0.0045(17) 0.0034(17) C1 0.024(2) 0.032(2) 0.025(2) -0.0012(19) -0.0038(17) 0.0036(18) C3 0.027(2) 0.037(3) 0.037(3) 0.012(2) 0.011(2) 0.009(2) C7 0.027(2) 0.037(3) 0.032(2) -0.009(2) -0.0057(18) 0.003(2) C5 0.041(3) 0.040(3) 0.038(3) 0.000(2) 0.010(2) -0.006(2) C6 0.046(3) 0.041(3) 0.045(3) 0.009(3) -0.019(2) -0.004(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 F5 F6 1.11(2) . ? F5 F4 1.14(5) . ? F5 B1 1.515(14) . ? F5 F7 1.64(2) . ? F3 F4 0.86(5) . ? F3 F3 0.95(5) 8_575 ? F3 F2 0.97(3) . ? F3 B1 1.32(3) . ? F3 F4 1.74(8) 8_575 ? C1S O1S 1.425(8) . ? F10 F10 0.88(4) 8_575 ? F10 B2 1.333(17) . ? C2S O2S 1.529(15) . ? O3S C3S 1.53(3) . ? B2 F10 1.333(17) 8_575 ? B2 F8 1.378(14) . ? B2 F9 1.393(10) . ? B2 F9 1.393(10) 8_575 ? B1 F3 1.32(3) 8_575 ? B1 F7 1.351(19) . ? B1 F7 1.351(19) 8_575 ? B1 F1 1.369(19) . ? B1 F2 1.45(4) . ? B1 F6 1.47(2) 8_575 ? B1 F6 1.47(2) . ? B1 F5 1.515(14) 8_575 ? B1 F4 1.54(5) 8_575 ? B1 F4 1.54(5) . ? Cu1 O1 1.968(3) . ? Cu1 O1 1.968(3) 8_575 ? Cu1 O3 1.973(3) . ? Cu1 O3 1.973(3) 8_575 ? Cu1 O1S 2.126(4) . ? Cu1 Cu2 2.6586(11) . ? Cu2 O2 1.957(3) . ? Cu2 O2 1.957(3) 8_575 ? Cu2 O4 1.957(3) 8_575 ? Cu2 O4 1.957(3) . ? Cu2 O2S 2.127(4) . ? O2 C1 1.251(5) . ? O3 C2 1.255(5) . ? O4 C2 1.248(5) . ? O1 C1 1.255(5) . ? O2S C2S 1.529(15) 8_575 ? N2 C4 1.328(6) . ? N2 C6 1.369(7) . ? N2 C7 1.462(6) . ? C4 N1 1.324(6) 2_475 ? N1 C4 1.324(6) 2_474 ? N1 C5 1.375(6) . ? N1 C3 1.464(5) . ? C2 C3 1.522(6) . ? C1 C7 1.523(6) . ? C5 C6 1.340(7) 2_474 ? C6 C5 1.340(7) 2_475 ? F7 F7 0.60(4) 8_575 ? F7 F6 0.96(2) . ? F7 F6 1.43(3) 8_575 ? F2 F3 0.97(3) 8_575 ? F2 F4 1.33(6) . ? F2 F4 1.33(6) 8_575 ? F6 F7 1.43(3) 8_575 ? F4 F3 1.74(8) 8_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 F6 F5 F4 131(3) . . ? F6 F5 B1 66.3(15) . . ? F4 F5 B1 69(3) . . ? F6 F5 F7 34.7(13) . . ? F4 F5 F7 100(3) . . ? B1 F5 F7 50.6(9) . . ? F4 F3 F3 148(4) . 8_575 ? F4 F3 F2 93(4) . . ? F3 F3 F2 61(2) 8_575 . ? F4 F3 B1 88(4) . . ? F3 F3 B1 68.8(12) 8_575 . ? F2 F3 B1 77(3) . . ? F4 F3 F4 132(6) . 8_575 ? F3 F3 F4 15.3(18) 8_575 8_575 ? F2 F3 F4 49(3) . 8_575 ? B1 F3 F4 59(2) . 8_575 ? F10 F10 B2 70.8(8) 8_575 . ? F10 B2 F10 38.5(16) . 8_575 ? F10 B2 F8 111.4(13) . . ? F10 B2 F8 111.4(13) 8_575 . ? F10 B2 F9 96.2(8) . . ? F10 B2 F9 128.8(13) 8_575 . ? F8 B2 F9 106.8(8) . . ? F10 B2 F9 128.8(13) . 8_575 ? F10 B2 F9 96.2(8) 8_575 8_575 ? F8 B2 F9 106.8(8) . 8_575 ? F9 B2 F9 104.1(11) . 8_575 ? F3 B1 F3 42(3) . 8_575 ? F3 B1 F7 125.0(18) . . ? F3 B1 F7 137(2) 8_575 . ? F3 B1 F7 137(2) . 8_575 ? F3 B1 F7 125.0(18) 8_575 8_575 ? F7 B1 F7 25.8(17) . 8_575 ? F3 B1 F1 100.9(16) . . ? F3 B1 F1 100.9(16) 8_575 . ? F7 B1 F1 121.4(15) . . ? F7 B1 F1 121.4(15) 8_575 . ? F3 B1 F2 40.7(13) . . ? F3 B1 F2 40.7(13) 8_575 . ? F7 B1 F2 100.2(19) . . ? F7 B1 F2 100.2(19) 8_575 . ? F1 B1 F2 137.2(19) . . ? F3 B1 F6 159.5(18) . 8_575 ? F3 B1 F6 118.5(16) 8_575 8_575 ? F7 B1 F6 60.8(15) . 8_575 ? F7 B1 F6 39.5(10) 8_575 8_575 ? F1 B1 F6 89.3(13) . 8_575 ? F2 B1 F6 122.2(16) . 8_575 ? F3 B1 F6 118.5(16) . . ? F3 B1 F6 159.5(18) 8_575 . ? F7 B1 F6 39.5(10) . . ? F7 B1 F6 60.8(15) 8_575 . ? F1 B1 F6 89.3(14) . . ? F2 B1 F6 122.2(16) . . ? F6 B1 F6 79(2) 8_575 . ? F3 B1 F5 75.3(14) . . ? F3 B1 F5 117.6(17) 8_575 . ? F7 B1 F5 69.4(11) . . ? F7 B1 F5 95.1(13) 8_575 . ? F1 B1 F5 93.1(9) . . ? F2 B1 F5 92.6(10) . . ? F6 B1 F5 122.2(17) 8_575 . ? F6 B1 F5 43.5(9) . . ? F3 B1 F5 117.6(17) . 8_575 ? F3 B1 F5 75.3(14) 8_575 8_575 ? F7 B1 F5 95.1(13) . 8_575 ? F7 B1 F5 69.4(11) 8_575 8_575 ? F1 B1 F5 93.1(9) . 8_575 ? F2 B1 F5 92.6(10) . 8_575 ? F6 B1 F5 43.5(9) 8_575 8_575 ? F6 B1 F5 122.2(17) . 8_575 ? F5 B1 F5 164.3(17) . 8_575 ? F3 B1 F4 74(3) . 8_575 ? F3 B1 F4 34(2) 8_575 8_575 ? F7 B1 F4 116(2) . 8_575 ? F7 B1 F4 95(2) 8_575 8_575 ? F1 B1 F4 109(2) . 8_575 ? F2 B1 F4 53(2) . 8_575 ? F6 B1 F4 86(2) 8_575 8_575 ? F6 B1 F4 156(3) . 8_575 ? F5 B1 F4 145(3) . 8_575 ? F5 B1 F4 44(2) 8_575 8_575 ? F3 B1 F4 34(2) . . ? F3 B1 F4 74(3) 8_575 . ? F7 B1 F4 95(2) . . ? F7 B1 F4 116(2) 8_575 . ? F1 B1 F4 109.3(19) . . ? F2 B1 F4 53(2) . . ? F6 B1 F4 156(3) 8_575 . ? F6 B1 F4 86(2) . . ? F5 B1 F4 44(2) . . ? F5 B1 F4 145(3) 8_575 . ? F4 B1 F4 102(5) 8_575 . ? O1 Cu1 O1 89.5(2) . 8_575 ? O1 Cu1 O3 89.92(14) . . ? O1 Cu1 O3 168.94(13) 8_575 . ? O1 Cu1 O3 168.94(13) . 8_575 ? O1 Cu1 O3 89.92(14) 8_575 8_575 ? O3 Cu1 O3 88.52(19) . 8_575 ? O1 Cu1 O1S 96.00(13) . . ? O1 Cu1 O1S 96.00(13) 8_575 . ? O3 Cu1 O1S 95.04(13) . . ? O3 Cu1 O1S 95.04(13) 8_575 . ? O1 Cu1 Cu2 84.78(9) . . ? O1 Cu1 Cu2 84.78(9) 8_575 . ? O3 Cu1 Cu2 84.16(9) . . ? O3 Cu1 Cu2 84.16(9) 8_575 . ? O1S Cu1 Cu2 178.89(15) . . ? O2 Cu2 O2 89.2(2) . 8_575 ? O2 Cu2 O4 166.97(13) . 8_575 ? O2 Cu2 O4 89.82(14) 8_575 8_575 ? O2 Cu2 O4 89.82(14) . . ? O2 Cu2 O4 166.97(13) 8_575 . ? O4 Cu2 O4 88.2(2) 8_575 . ? O2 Cu2 O2S 97.87(14) . . ? O2 Cu2 O2S 97.87(14) 8_575 . ? O4 Cu2 O2S 95.13(14) 8_575 . ? O4 Cu2 O2S 95.13(14) . . ? O2 Cu2 Cu1 83.28(9) . . ? O2 Cu2 Cu1 83.27(9) 8_575 . ? O4 Cu2 Cu1 83.70(9) 8_575 . ? O4 Cu2 Cu1 83.70(9) . . ? O2S Cu2 Cu1 178.37(15) . . ? C1 O2 Cu2 123.3(3) . . ? C2 O3 Cu1 121.6(3) . . ? C2 O4 Cu2 123.1(3) . . ? C1 O1 Cu1 120.9(3) . . ? C1S O1S Cu1 122.2(4) . . ? C2S O2S C2S 124.6(12) 8_575 . ? C2S O2S Cu2 116.7(6) 8_575 . ? C2S O2S Cu2 116.7(6) . . ? C4 N2 C6 108.4(4) . . ? C4 N2 C7 125.4(4) . . ? C6 N2 C7 126.0(4) . . ? N1 C4 N2 108.6(4) 2_475 . ? C4 N1 C5 108.5(4) 2_474 . ? C4 N1 C3 124.9(4) 2_474 . ? C5 N1 C3 125.7(4) . . ? O4 C2 O3 127.4(4) . . ? O4 C2 C3 116.9(4) . . ? O3 C2 C3 115.7(4) . . ? O2 C1 O1 127.8(4) . . ? O2 C1 C7 117.3(4) . . ? O1 C1 C7 114.9(4) . . ? N1 C3 C2 110.5(4) . . ? N2 C7 C1 111.5(4) . . ? C6 C5 N1 107.0(5) 2_474 . ? C5 C6 N2 107.5(5) 2_475 . ? F7 F7 F6 131.4(17) 8_575 . ? F7 F7 B1 77.1(9) 8_575 . ? F6 F7 B1 77.1(17) . . ? F7 F7 F6 30.2(10) 8_575 8_575 ? F6 F7 F6 101(2) . 8_575 ? B1 F7 F6 63.8(12) . 8_575 ? F7 F7 F5 137.1(7) 8_575 . ? F6 F7 F5 40.9(16) . . ? B1 F7 F5 60.0(8) . . ? F6 F7 F5 116.8(13) 8_575 . ? F3 F2 F3 59(4) 8_575 . ? F3 F2 F4 97(4) 8_575 . ? F3 F2 F4 40(2) . . ? F3 F2 F4 40(2) 8_575 8_575 ? F3 F2 F4 97(4) . 8_575 ? F4 F2 F4 129(5) . 8_575 ? F3 F2 B1 63(2) 8_575 . ? F3 F2 B1 63(2) . . ? F4 F2 B1 67(2) . . ? F4 F2 B1 67(3) 8_575 . ? F7 F6 F5 104(2) . . ? F7 F6 F7 18.4(13) . 8_575 ? F5 F6 F7 112(2) . 8_575 ? F7 F6 B1 63.4(16) . . ? F5 F6 B1 70.3(14) . . ? F7 F6 B1 55.4(12) 8_575 . ? F3 F4 F5 120(6) . . ? F3 F4 F2 47(3) . . ? F5 F4 F2 120(4) . . ? F3 F4 B1 58(4) . . ? F5 F4 B1 67(3) . . ? F2 F4 B1 60(3) . . ? F3 F4 F3 17(2) . 8_575 ? F5 F4 F3 113(4) . 8_575 ? F2 F4 F3 33(2) . 8_575 ? B1 F4 F3 47(2) . 8_575 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 73.36 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.977 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 907228' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 B2 Cu2 F8 N4 O8' _chemical_formula_weight 666.99 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' B B 0.0090 0.0039 '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' F F 0.0727 0.0534 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 15.6203(16) _cell_length_b 11.564(2) _cell_length_c 14.8705(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2686.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 817 _cell_measurement_theta_min 4.10 _cell_measurement_theta_max 76.02 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.1104 _exptl_crystal_size_mid 0.1057 _exptl_crystal_size_min 0.0618 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 2.889 _exptl_absorpt_correction_T_min 0.116 _exptl_absorpt_correction_T_max 0.343 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9024 _diffrn_reflns_av_R_equivalents 0.1062 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 67.98 _reflns_number_total 2568 _reflns_number_gt 1340 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1373P)^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 2568 _refine_ls_number_parameters 204 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1507 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.2015 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 1.056 _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 F7B F -0.2360(6) 0.1927(13) 0.4055(7) 0.086(4) Uani 0.50 1 d PD . 1 F7A F -0.1924(9) 0.1253(9) 0.4057(7) 0.086(4) Uani 0.50 1 d PD . 2 B1 B 0.3700(6) 0.2124(10) 0.6783(7) 0.11(2) Uani 0.50 1 d PD . . B2 B -0.1613(6) 0.2500 0.3998(6) 0.060(4) Uani 1 2 d SD . . F5 F -0.1065(4) 0.2500 0.4731(4) 0.081(3) Uani 1 2 d SD . . C5 C 0.3073(7) -0.0800(10) 0.4090(9) 0.087(4) Uani 1 1 d . . . H5 H 0.2901 -0.1129 0.4647 0.105 Uiso 1 1 calc R . . C4 C 0.1121(6) 0.0795(10) 0.8743(7) 0.071(3) Uani 1 1 d . . . H4 H 0.0623 0.1122 0.9008 0.086 Uiso 1 1 calc R . . F2 F 0.3325(5) 0.2500 0.7601(5) 0.082(2) Uani 1 2 d SD . . F4 F 0.4549(4) 0.2500 0.6725(6) 0.089(3) Uani 1 2 d SD . . F6 F -0.1191(5) 0.2500 0.3172(4) 0.072(2) Uani 1 2 d SD . . F3 F 0.3703(6) 0.0895(6) 0.6731(7) 0.082(4) Uani 0.50 1 d PD . . Cu1 Cu 0.18993(10) 0.2500 0.55995(11) 0.0501(5) Uani 1 2 d S . . Cu2 Cu 0.03000(9) 0.2500 0.50546(11) 0.0460(5) Uani 1 2 d S . . F1 F 0.3207(4) 0.2500 0.6047(5) 0.077(2) Uani 1 2 d SD . . O4 O 0.0693(3) 0.1297(6) 0.4233(4) 0.0528(14) Uani 1 1 d . . . O2 O 0.0114(3) 0.1326(5) 0.5983(4) 0.0519(14) Uani 1 1 d . . . O3 O 0.2060(4) 0.1315(6) 0.4702(4) 0.0607(17) Uani 1 1 d . . . O1 O 0.1479(4) 0.1354(7) 0.6429(4) 0.079(2) Uani 1 1 d . . . N2 N 0.2561(5) -0.0247(7) 0.3489(5) 0.0589(19) Uani 1 1 d . . . C2 C 0.0497(5) 0.0197(8) 0.7248(6) 0.054(2) Uani 1 1 d . . . H2A H -0.0059 0.0416 0.7518 0.064 Uiso 1 1 calc R . . H2B H 0.0443 -0.0596 0.7002 0.064 Uiso 1 1 calc R . . N1 N 0.1167(4) 0.0226(7) 0.7933(5) 0.0514(17) Uani 1 1 d . . . C7 C 0.1454(5) 0.0946(8) 0.4233(6) 0.053(2) Uani 1 1 d . . . C1 C 0.0725(5) 0.1039(9) 0.6494(6) 0.056(2) Uani 1 1 d . . . C3 C 0.3024(5) 0.0083(9) 0.2797(6) 0.061(2) Uani 1 1 d . . . H3 H 0.2814 0.0479 0.2282 0.073 Uiso 1 1 calc R . . C6 C 0.1637(5) -0.0035(10) 0.3598(8) 0.073(3) Uani 1 1 d . . . H6A H 0.1360 -0.0746 0.3827 0.087 Uiso 1 1 calc R . . H6B H 0.1384 0.0144 0.3003 0.087 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 F7B 0.067(8) 0.113(11) 0.080(8) 0.009(8) -0.003(6) -0.018(7) F7A 0.101(10) 0.092(10) 0.067(8) -0.010(7) 0.029(8) -0.046(8) B1 0.024(8) 0.28(8) 0.033(9) 0.025(19) -0.008(6) -0.018(18) B2 0.033(7) 0.101(13) 0.047(8) 0.000 -0.001(6) 0.000 F5 0.043(4) 0.127(8) 0.074(5) 0.000 -0.006(4) 0.000 C5 0.084(8) 0.077(8) 0.101(9) 0.027(7) 0.039(7) 0.013(6) C4 0.057(6) 0.086(7) 0.071(6) -0.014(6) -0.015(5) 0.020(5) F2 0.075(5) 0.100(7) 0.072(5) 0.000 0.006(4) 0.000 F4 0.044(4) 0.127(8) 0.095(6) 0.000 -0.010(4) 0.000 F6 0.085(5) 0.073(5) 0.058(4) 0.000 0.013(4) 0.000 F3 0.084(8) 0.084(9) 0.080(8) 0.003(7) -0.010(7) -0.002(7) Cu1 0.0357(9) 0.0676(12) 0.0469(9) 0.000 -0.0001(7) 0.000 Cu2 0.0331(8) 0.0578(11) 0.0473(9) 0.000 -0.0002(7) 0.000 F1 0.037(4) 0.116(7) 0.077(5) 0.000 -0.010(4) 0.000 O4 0.038(3) 0.069(4) 0.051(3) -0.004(3) 0.001(2) -0.003(3) O2 0.038(3) 0.064(4) 0.054(3) 0.004(3) -0.005(3) -0.003(3) O3 0.042(3) 0.067(4) 0.073(4) -0.015(3) 0.001(3) 0.002(3) O1 0.037(3) 0.126(6) 0.074(4) 0.045(4) -0.002(3) -0.007(4) N2 0.047(4) 0.063(5) 0.067(5) -0.009(4) 0.005(4) -0.004(4) C2 0.040(4) 0.069(6) 0.052(5) 0.000(4) 0.003(4) 0.002(4) N1 0.038(3) 0.065(5) 0.052(4) 0.007(4) -0.005(3) 0.003(3) C7 0.042(5) 0.060(5) 0.057(5) -0.004(4) 0.010(4) -0.010(4) C1 0.041(5) 0.074(7) 0.053(5) 0.001(5) 0.000(4) -0.001(4) C3 0.045(5) 0.089(7) 0.047(5) -0.008(5) 0.000(4) 0.009(5) C6 0.039(4) 0.085(7) 0.093(8) -0.033(6) 0.015(5) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F7B F7B 1.33(3) 7_565 ? F7B B2 1.345(8) . ? F7A B2 1.524(7) . ? B1 B1 0.87(2) 7_565 ? B1 F4 1.398(9) . ? B1 F1 1.406(9) . ? B1 F2 1.419(9) . ? B1 F3 1.423(10) . ? B2 F7B 1.345(8) 7_565 ? B2 F5 1.386(8) . ? B2 F6 1.393(8) . ? B2 F7A 1.524(7) 7_565 ? F5 Cu2 2.186(6) . ? C5 N2 1.359(13) . ? C5 C4 1.362(13) 2_554 ? C4 C5 1.362(13) 2 ? C4 N1 1.375(12) . ? F2 B1 1.419(9) 7_565 ? F4 B1 1.398(9) 7_565 ? Cu1 O1 1.926(7) . ? Cu1 O1 1.926(7) 7_565 ? Cu1 O3 1.930(6) . ? Cu1 O3 1.930(6) 7_565 ? Cu1 F1 2.149(6) . ? Cu1 Cu2 2.626(2) . ? Cu2 O4 1.950(6) . ? Cu2 O4 1.950(6) 7_565 ? Cu2 O2 1.958(6) 7_565 ? Cu2 O2 1.958(6) . ? F1 B1 1.406(9) 7_565 ? O4 C7 1.255(9) . ? O2 C1 1.264(10) . ? O3 C7 1.251(10) . ? O1 C1 1.237(10) . ? N2 C3 1.315(11) . ? N2 C6 1.473(11) . ? C2 N1 1.461(10) . ? C2 C1 1.528(12) . ? N1 C3 1.329(10) 2 ? C7 C6 1.504(13) . ? C3 N1 1.329(10) 2_554 ? 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 F7B F7B B2 60.5(7) 7_565 . ? B1 B1 F4 71.9(5) 7_565 . ? B1 B1 F1 72.0(5) 7_565 . ? F4 B1 F1 112.0(8) . . ? B1 B1 F2 72.2(5) 7_565 . ? F4 B1 F2 110.4(9) . . ? F1 B1 F2 110.3(8) . . ? B1 B1 F3 176.9(6) 7_565 . ? F4 B1 F3 107.7(8) . . ? F1 B1 F3 105.6(8) . . ? F2 B1 F3 110.7(8) . . ? F7B B2 F7B 59.1(14) . 7_565 ? F7B B2 F5 119.0(7) . . ? F7B B2 F5 119.0(7) 7_565 . ? F7B B2 F6 117.8(7) . . ? F7B B2 F6 117.8(7) 7_565 . ? F5 B2 F6 113.7(7) . . ? F7B B2 F7A 41.7(6) . . ? F7B B2 F7A 100.7(13) 7_565 . ? F5 B2 F7A 98.7(6) . . ? F6 B2 F7A 101.6(5) . . ? F7B B2 F7A 100.7(13) . 7_565 ? F7B B2 F7A 41.7(6) 7_565 7_565 ? F5 B2 F7A 98.7(6) . 7_565 ? F6 B2 F7A 101.6(5) . 7_565 ? F7A B2 F7A 142.1(14) . 7_565 ? B2 F5 Cu2 140.8(6) . . ? N2 C5 C4 107.1(10) . 2_554 ? C5 C4 N1 106.6(9) 2 . ? B1 F2 B1 35.7(10) . 7_565 ? B1 F4 B1 36.2(10) . 7_565 ? O1 Cu1 O1 86.9(5) . 7_565 ? O1 Cu1 O3 90.0(3) . . ? O1 Cu1 O3 167.5(3) 7_565 . ? O1 Cu1 O3 167.5(3) . 7_565 ? O1 Cu1 O3 90.0(3) 7_565 7_565 ? O3 Cu1 O3 90.5(4) . 7_565 ? O1 Cu1 F1 97.2(2) . . ? O1 Cu1 F1 97.2(2) 7_565 . ? O3 Cu1 F1 95.2(2) . . ? O3 Cu1 F1 95.2(2) 7_565 . ? O1 Cu1 Cu2 82.71(18) . . ? O1 Cu1 Cu2 82.71(18) 7_565 . ? O3 Cu1 Cu2 84.87(18) . . ? O3 Cu1 Cu2 84.87(18) 7_565 . ? F1 Cu1 Cu2 179.9(2) . . ? O4 Cu2 O4 91.0(4) . 7_565 ? O4 Cu2 O2 169.4(2) . 7_565 ? O4 Cu2 O2 89.6(3) 7_565 7_565 ? O4 Cu2 O2 89.6(3) . . ? O4 Cu2 O2 169.4(2) 7_565 . ? O2 Cu2 O2 87.8(4) 7_565 . ? O4 Cu2 F5 99.7(2) . . ? O4 Cu2 F5 99.7(2) 7_565 . ? O2 Cu2 F5 90.6(2) 7_565 . ? O2 Cu2 F5 90.6(2) . . ? O4 Cu2 Cu1 83.90(16) . . ? O4 Cu2 Cu1 83.90(16) 7_565 . ? O2 Cu2 Cu1 85.62(16) 7_565 . ? O2 Cu2 Cu1 85.62(16) . . ? F5 Cu2 Cu1 174.7(2) . . ? B1 F1 B1 36.0(10) 7_565 . ? B1 F1 Cu1 139.6(6) 7_565 . ? B1 F1 Cu1 139.6(6) . . ? C7 O4 Cu2 121.9(6) . . ? C1 O2 Cu2 119.6(6) . . ? C7 O3 Cu1 121.9(6) . . ? C1 O1 Cu1 125.3(6) . . ? C3 N2 C5 109.2(8) . . ? C3 N2 C6 125.2(9) . . ? C5 N2 C6 125.7(9) . . ? N1 C2 C1 109.3(7) . . ? C3 N1 C4 108.2(7) 2 . ? C3 N1 C2 124.7(8) 2 . ? C4 N1 C2 125.8(7) . . ? O3 C7 O4 127.4(8) . . ? O3 C7 C6 117.6(8) . . ? O4 C7 C6 115.1(8) . . ? O1 C1 O2 126.5(9) . . ? O1 C1 C2 117.8(8) . . ? O2 C1 C2 115.6(7) . . ? N2 C3 N1 109.0(9) . 2_554 ? N2 C6 C7 112.4(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.835 _refine_diff_density_min -0.835 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 946321' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 Cu3 F6 N4 O14 Si' _chemical_formula_weight 833.13 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' 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' F F 0.0727 0.0534 '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' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 12.4176(2) _cell_length_b 22.5346(3) _cell_length_c 10.1644(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.054(2) _cell_angle_gamma 90.00 _cell_volume 2719.19(8) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 5188 _cell_measurement_theta_min 3.92 _cell_measurement_theta_max 74.47 _exptl_crystal_description 'small plate' _exptl_crystal_colour blue _exptl_crystal_size_max 0.105 _exptl_crystal_size_mid 0.046 _exptl_crystal_size_min 0.026 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 4.233 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.694 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.2273 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9363 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 74.50 _reflns_number_total 3687 _reflns_number_gt 3562 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+2.9698P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 3687 _refine_ls_number_parameters 420 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1578(3) 0.64303(17) 0.8840(5) 0.0172(8) Uani 1 1 d . . . C1S C 0.1664(5) 0.6511(3) 0.3572(7) 0.0459(14) Uani 1 1 d . . . H1S1 H 0.1914 0.6901 0.3973 0.069 Uiso 1 1 calc R . . H1S2 H 0.1037 0.6561 0.2730 0.069 Uiso 1 1 calc R . . H1S3 H 0.2290 0.6311 0.3351 0.069 Uiso 1 1 calc R . . C2 C 0.1161(4) 0.70667(18) 0.8590(5) 0.0221(9) Uani 1 1 d . . . H2A H 0.1610 0.7276 0.8073 0.026 Uiso 1 1 calc R . . H2B H 0.0368 0.7062 0.8005 0.026 Uiso 1 1 calc R . . C2S C 0.4528(5) 0.6543(2) 1.2550(6) 0.0408(13) Uani 1 1 d . . . H2S1 H 0.5291 0.6467 1.3151 0.061 Uiso 1 1 calc R . . H2S2 H 0.3996 0.6278 1.2803 0.061 Uiso 1 1 calc R . . H2S3 H 0.4323 0.6956 1.2656 0.061 Uiso 1 1 calc R . . C3 C 0.0399(3) 0.74712(17) 1.0415(4) 0.0179(8) Uani 1 1 d . . . H10 H -0.0337 0.7309 1.0080 0.021 Uiso 1 1 calc R . . C4 C 0.2169(4) 0.7700(2) 1.0638(5) 0.0296(9) Uani 1 1 d . . . H14 H 0.2884 0.7721 1.0476 0.035 Uiso 1 1 calc R . . C5 C 0.6877(4) 0.2953(2) 1.1683(5) 0.0296(9) Uani 1 1 d . . . H13 H 0.7348 0.3191 1.2394 0.035 Uiso 1 1 calc R . . C6 C 0.5112(4) 0.29910(18) 1.2441(5) 0.0190(8) Uani 1 1 d . . . H4A H 0.5601 0.2974 1.3405 0.023 Uiso 1 1 calc R . . H4B H 0.4492 0.2704 1.2351 0.023 Uiso 1 1 calc R . . C7 C 0.4613(3) 0.36091(17) 1.2161(4) 0.0177(8) Uani 1 1 d . . . C8 C 0.5498(3) 0.48951(17) 0.8841(4) 0.0155(8) Uani 1 1 d . . . C9 C 0.6592(3) 0.4970(2) 0.8459(5) 0.0185(8) Uani 1 1 d . . . H6A H 0.6547 0.4730 0.7627 0.022 Uiso 1 1 calc R . . H6B H 0.6673 0.5391 0.8228 0.022 Uiso 1 1 calc R . . C10 C 0.8090(4) 0.42393(18) 0.9746(4) 0.0227(8) Uani 1 1 d . . . H9 H 0.7867 0.3904 0.9163 0.027 Uiso 1 1 calc R . . C11 C -0.1043(4) 0.42639(19) 1.0916(5) 0.0243(8) Uani 1 1 d . . . H12 H -0.0531 0.3953 1.1302 0.029 Uiso 1 1 calc R . . C12 C -0.1880(4) 0.51405(17) 1.0603(5) 0.0201(8) Uani 1 1 d . . . H11 H -0.2065 0.5542 1.0726 0.024 Uiso 1 1 calc R . . C13 C -0.0170(4) 0.5077(2) 1.2603(4) 0.0192(8) Uani 1 1 d . . . H8A H -0.0046 0.4813 1.3411 0.023 Uiso 1 1 calc R . . H8B H -0.0410 0.5470 1.2850 0.023 Uiso 1 1 calc R . . C14 C 0.0921(3) 0.51418(16) 1.2218(4) 0.0141(7) Uani 1 1 d . . . N1 N 0.1227(3) 0.74027(14) 0.9845(4) 0.0185(7) Uani 1 1 d . . . N2 N 0.5773(3) 0.28048(14) 1.1532(3) 0.0185(7) Uani 1 1 d . . . N3 N 0.7590(3) 0.47900(16) 0.9558(4) 0.0195(7) Uani 1 1 d . . . N4 N -0.1047(3) 0.48298(15) 1.1443(3) 0.0177(6) Uani 1 1 d . . . O1S O 0.1307(3) 0.61676(17) 0.4520(4) 0.0408(9) Uani 1 1 d . . . H1S H 0.1080 0.6392 0.5042 0.061 Uiso 1 1 calc R . . O1W O 0.4179(3) 0.11881(16) -0.1054(4) 0.0326(7) Uani 1 1 d D . . H1W1 H 0.473(3) 0.107(3) -0.042(4) 0.049 Uiso 1 1 d D . . H1W2 H 0.024(4) 0.276(2) 0.025(5) 0.049 Uiso 1 1 d D . . O2S O 0.4493(3) 0.64402(16) 1.1182(4) 0.0379(8) Uani 1 1 d . . . H2S H 0.5140 0.6487 1.1094 0.057 Uiso 1 1 calc R . . O2W O -0.0237(3) 0.30375(15) 0.0085(4) 0.0345(8) Uani 1 1 d D . . H2W1 H 0.357(2) 0.124(3) -0.087(5) 0.052 Uiso 1 1 d D . . H2W2 H -0.065(4) 0.308(3) -0.073(2) 0.052 Uiso 1 1 d D . . O6 O 0.4121(3) 0.37796(13) 1.3016(3) 0.0223(6) Uani 1 1 d . . . F1 F 0.1257(2) 0.20954(12) 0.0795(3) 0.0282(6) Uani 1 1 d . . . F2 F 0.2925(2) 0.21184(12) 0.2741(3) 0.0317(6) Uani 1 1 d . . . F3 F 0.2191(2) 0.14164(12) -0.0344(3) 0.0293(6) Uani 1 1 d . . . F4 F 0.3018(2) 0.23415(13) 0.0465(3) 0.0364(6) Uani 1 1 d . . . F5 F 0.3820(2) 0.14492(13) 0.1600(3) 0.0353(6) Uani 1 1 d . . . F6 F 0.2041(3) 0.11980(12) 0.1868(3) 0.0358(6) Uani 1 1 d . . . Si1 Si 0.25546(10) 0.17767(5) 0.12006(12) 0.0207(2) Uani 1 1 d . . . O1 O 0.3559(2) 0.54702(12) 0.9935(3) 0.0123(5) Uani 1 1 d D . . H1O1 H 0.384(4) 0.5795(11) 1.028(5) 0.018 Uiso 1 1 d D . . O2 O 0.2758(2) 0.54084(12) 0.6011(3) 0.0128(5) Uani 1 1 d D . . H1O2 H 0.225(3) 0.5654(17) 0.564(5) 0.019 Uiso 1 1 d D . . O3 O 0.1728(2) 0.62125(12) 1.0025(3) 0.0195(6) Uani 1 1 d . . . O4 O 0.1682(3) 0.61713(13) 0.7804(3) 0.0257(6) Uani 1 1 d . . . O5 O 0.4723(3) 0.38844(12) 1.1135(3) 0.0212(6) Uani 1 1 d . . . O7 O 0.5578(2) 0.48169(13) 1.0096(3) 0.0162(6) Uani 1 1 d . . . O8 O 0.4612(2) 0.49278(13) 0.7869(3) 0.0162(6) Uani 1 1 d . . . O9 O 0.0812(2) 0.52689(13) 1.0979(3) 0.0174(6) Uani 1 1 d . . . O10 O 0.1835(2) 0.49245(13) 0.8138(3) 0.0169(6) Uani 1 1 d . . . Cu1 Cu 0.42268(4) 0.46962(2) 1.06485(5) 0.01293(12) Uani 1 1 d . . . Cu2 Cu 0.31085(5) 0.55299(2) 0.79600(6) 0.01207(11) Uani 1 1 d . . . Cu3 Cu 0.21609(4) 0.53871(2) 1.04069(5) 0.01370(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0162(18) 0.0172(17) 0.020(2) -0.0023(16) 0.0090(16) 0.0000(15) C1S 0.048(3) 0.035(3) 0.053(4) 0.006(3) 0.012(3) 0.000(3) C2 0.037(3) 0.0163(19) 0.016(2) 0.0023(16) 0.0121(18) 0.0020(17) C2S 0.056(4) 0.036(3) 0.032(3) -0.012(2) 0.016(3) -0.003(3) C3 0.021(2) 0.0150(16) 0.0184(18) 0.0016(14) 0.0063(17) 0.0010(16) C4 0.023(2) 0.032(2) 0.036(3) -0.009(2) 0.0125(18) -0.0053(19) C5 0.021(2) 0.035(2) 0.032(2) -0.0095(19) 0.0066(18) -0.0051(18) C6 0.025(2) 0.0167(18) 0.018(2) -0.0013(15) 0.0092(17) 0.0023(16) C7 0.021(2) 0.0153(17) 0.018(2) -0.0015(15) 0.0070(16) -0.0001(15) C8 0.0160(19) 0.0159(17) 0.015(2) 0.0003(15) 0.0048(16) 0.0007(15) C9 0.0098(17) 0.031(2) 0.015(2) 0.0029(16) 0.0044(15) 0.0025(15) C10 0.025(2) 0.0197(19) 0.022(2) -0.0012(15) 0.0048(17) 0.0001(16) C11 0.021(2) 0.025(2) 0.024(2) 0.0016(17) 0.0031(16) 0.0056(17) C12 0.0185(18) 0.020(2) 0.023(2) -0.0007(17) 0.0073(16) 0.0009(17) C13 0.0165(19) 0.029(2) 0.012(2) 0.0001(16) 0.0041(16) -0.0031(16) C14 0.0141(18) 0.0138(16) 0.016(2) -0.0009(14) 0.0063(16) 0.0004(14) N1 0.0261(18) 0.0137(14) 0.0176(16) -0.0010(13) 0.0094(14) 0.0014(13) N2 0.0232(17) 0.0144(15) 0.0178(17) -0.0013(12) 0.0060(14) 0.0022(13) N3 0.0150(16) 0.0244(17) 0.0193(17) 0.0033(14) 0.0052(14) 0.0017(13) N4 0.0132(15) 0.0244(16) 0.0139(16) 0.0003(13) 0.0015(12) -0.0010(13) O1S 0.050(2) 0.044(2) 0.033(2) 0.0112(16) 0.0183(18) 0.0208(18) O1W 0.0281(17) 0.0405(19) 0.0297(18) 0.0006(14) 0.0093(14) 0.0062(14) O2S 0.043(2) 0.0411(19) 0.0348(19) -0.0167(16) 0.0197(16) -0.0228(17) O2W 0.0350(19) 0.0318(18) 0.033(2) -0.0036(15) 0.0047(15) 0.0065(15) O6 0.0309(16) 0.0220(13) 0.0175(15) 0.0004(11) 0.0125(12) 0.0032(12) F1 0.0233(13) 0.0329(13) 0.0283(14) -0.0023(11) 0.0074(10) 0.0075(10) F2 0.0269(15) 0.0395(14) 0.0249(15) -0.0072(11) 0.0015(11) 0.0065(11) F3 0.0301(13) 0.0337(13) 0.0217(12) -0.0036(10) 0.0038(10) 0.0077(11) F4 0.0328(14) 0.0402(14) 0.0361(16) 0.0059(12) 0.0100(12) -0.0066(12) F5 0.0268(13) 0.0456(17) 0.0281(14) -0.0064(12) -0.0003(11) 0.0135(12) F6 0.0411(16) 0.0342(14) 0.0302(15) 0.0068(11) 0.0075(12) -0.0023(12) Si1 0.0197(5) 0.0230(5) 0.0189(5) 0.0004(4) 0.0046(4) 0.0030(4) O1 0.0127(13) 0.0123(11) 0.0119(13) -0.0016(10) 0.0038(11) -0.0019(10) O2 0.0117(13) 0.0153(12) 0.0117(14) 0.0002(10) 0.0039(11) 0.0022(10) O3 0.0230(15) 0.0196(13) 0.0180(15) 0.0027(11) 0.0089(12) 0.0047(11) O4 0.0374(17) 0.0224(14) 0.0199(15) -0.0024(12) 0.0127(13) 0.0065(13) O5 0.0294(16) 0.0184(13) 0.0197(15) 0.0046(11) 0.0135(12) 0.0044(12) O7 0.0165(14) 0.0238(13) 0.0087(13) 0.0017(11) 0.0044(11) 0.0021(11) O8 0.0112(13) 0.0240(14) 0.0106(14) 0.0015(11) -0.0014(11) 0.0012(11) O9 0.0113(13) 0.0278(15) 0.0132(14) 0.0058(12) 0.0038(11) 0.0026(12) O10 0.0132(14) 0.0247(14) 0.0107(14) 0.0004(11) 0.0004(11) -0.0035(11) Cu1 0.0125(3) 0.0157(3) 0.0115(3) 0.0021(2) 0.0051(2) 0.0016(2) Cu2 0.0145(2) 0.0137(2) 0.0090(2) 0.0000(2) 0.00488(18) -0.0006(2) Cu3 0.0114(3) 0.0176(2) 0.0129(3) 0.0037(2) 0.0048(2) 0.0020(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 C1 O4 1.243(5) . ? C1 O3 1.263(5) . ? C1 C2 1.521(5) . ? C1S O1S 1.405(7) . ? C2 N1 1.465(5) . ? C2S O2S 1.398(6) . ? C3 N2 1.327(5) 3_455 ? C3 N1 1.328(5) . ? C4 C5 1.345(7) 3_455 ? C4 N1 1.384(6) . ? C5 C4 1.345(7) 3_545 ? C5 N2 1.375(6) . ? C6 N2 1.466(5) . ? C6 C7 1.517(5) . ? C7 O5 1.255(5) . ? C7 O6 1.259(5) . ? C8 O8 1.246(5) . ? C8 O7 1.262(5) . ? C8 C9 1.528(5) . ? C9 N3 1.461(5) . ? C10 C11 1.351(6) 1_655 ? C10 N3 1.376(5) . ? C11 C10 1.351(6) 1_455 ? C11 N4 1.384(5) . ? C12 N4 1.331(5) . ? C12 N3 1.332(6) 1_455 ? C13 N4 1.461(5) . ? C13 C14 1.524(5) . ? C14 O10 1.250(5) 2_565 ? C14 O9 1.259(5) . ? N2 C3 1.327(5) 3_545 ? N3 C12 1.332(6) 1_655 ? O6 Cu2 1.991(3) 2_565 ? F1 Si1 1.700(3) . ? F2 Si1 1.683(3) . ? F3 Si1 1.707(3) . ? F4 Si1 1.662(3) . ? F5 Si1 1.675(3) . ? F6 Si1 1.679(3) . ? O1 Cu2 1.924(3) . ? O1 Cu3 1.942(3) . ? O1 Cu1 1.976(3) . ? O2 Cu2 1.919(3) . ? O2 Cu3 1.968(3) 2_564 ? O2 Cu1 1.978(3) 2_564 ? O3 Cu3 1.944(3) . ? O4 Cu2 2.255(3) . ? O5 Cu1 1.947(3) . ? O7 Cu1 1.939(3) . ? O8 Cu1 2.326(3) 2_564 ? O8 Cu2 2.332(3) . ? O9 Cu3 1.946(3) . ? O10 C14 1.250(5) 2_564 ? O10 Cu2 2.136(3) . ? Cu1 O2 1.978(3) 2_565 ? Cu1 O8 2.326(3) 2_565 ? Cu1 Cu3 2.9488(6) . ? Cu2 O6 1.991(3) 2_564 ? Cu3 O2 1.968(3) 2_565 ? 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 O4 C1 O3 127.0(4) . . ? O4 C1 C2 114.6(4) . . ? O3 C1 C2 118.3(4) . . ? N1 C2 C1 114.4(4) . . ? N2 C3 N1 108.5(3) 3_455 . ? C5 C4 N1 106.7(4) 3_455 . ? C4 C5 N2 107.4(4) 3_545 . ? N2 C6 C7 114.7(3) . . ? O5 C7 O6 128.0(4) . . ? O5 C7 C6 118.2(3) . . ? O6 C7 C6 113.8(4) . . ? O8 C8 O7 126.8(4) . . ? O8 C8 C9 115.8(4) . . ? O7 C8 C9 117.4(4) . . ? N3 C9 C8 113.1(3) . . ? C11 C10 N3 107.2(4) 1_655 . ? C10 C11 N4 106.6(4) 1_455 . ? N4 C12 N3 108.0(3) . 1_455 ? N4 C13 C14 109.7(3) . . ? O10 C14 O9 125.7(4) 2_565 . ? O10 C14 C13 118.5(3) 2_565 . ? O9 C14 C13 115.8(3) . . ? C3 N1 C4 108.7(3) . . ? C3 N1 C2 126.0(4) . . ? C4 N1 C2 125.4(4) . . ? C3 N2 C5 108.7(3) 3_545 . ? C3 N2 C6 125.5(4) 3_545 . ? C5 N2 C6 125.8(4) . . ? C12 N3 C10 109.1(3) 1_655 . ? C12 N3 C9 123.7(4) 1_655 . ? C10 N3 C9 127.1(4) . . ? C12 N4 C11 109.1(3) . . ? C12 N4 C13 124.9(3) . . ? C11 N4 C13 125.3(3) . . ? C7 O6 Cu2 130.4(3) . 2_565 ? F4 Si1 F5 91.26(16) . . ? F4 Si1 F6 177.20(17) . . ? F5 Si1 F6 90.02(16) . . ? F4 Si1 F2 91.82(15) . . ? F5 Si1 F2 89.73(14) . . ? F6 Si1 F2 90.68(15) . . ? F4 Si1 F1 89.77(15) . . ? F5 Si1 F1 178.83(16) . . ? F6 Si1 F1 88.93(15) . . ? F2 Si1 F1 90.79(14) . . ? F4 Si1 F3 89.07(15) . . ? F5 Si1 F3 89.38(13) . . ? F6 Si1 F3 88.45(15) . . ? F2 Si1 F3 178.76(15) . . ? F1 Si1 F3 90.09(14) . . ? Cu2 O1 Cu3 104.90(13) . . ? Cu2 O1 Cu1 114.04(13) . . ? Cu3 O1 Cu1 97.66(12) . . ? Cu2 O2 Cu3 113.74(14) . 2_564 ? Cu2 O2 Cu1 105.49(13) . 2_564 ? Cu3 O2 Cu1 96.72(12) 2_564 2_564 ? C1 O3 Cu3 121.1(3) . . ? C1 O4 Cu2 121.1(3) . . ? C7 O5 Cu1 124.9(3) . . ? C8 O7 Cu1 119.6(3) . . ? C8 O8 Cu1 132.4(3) . 2_564 ? C8 O8 Cu2 122.2(3) . . ? Cu1 O8 Cu2 83.52(9) 2_564 . ? C14 O9 Cu3 118.7(3) . . ? C14 O10 Cu2 123.0(3) 2_564 . ? O7 Cu1 O5 88.22(12) . . ? O7 Cu1 O1 94.31(12) . . ? O5 Cu1 O1 171.92(13) . . ? O7 Cu1 O2 174.01(12) . 2_565 ? O5 Cu1 O2 94.66(12) . 2_565 ? O1 Cu1 O2 82.14(11) . 2_565 ? O7 Cu1 O8 106.31(11) . 2_565 ? O5 Cu1 O8 97.83(12) . 2_565 ? O1 Cu1 O8 88.83(11) . 2_565 ? O2 Cu1 O8 78.54(11) 2_565 2_565 ? O7 Cu1 Cu3 135.04(9) . . ? O5 Cu1 Cu3 136.05(9) . . ? O1 Cu1 Cu3 40.74(8) . . ? O2 Cu1 Cu3 41.51(8) 2_565 . ? O8 Cu1 Cu3 79.34(7) 2_565 . ? O2 Cu2 O1 167.28(10) . . ? O2 Cu2 O6 95.22(12) . 2_564 ? O1 Cu2 O6 92.12(12) . 2_564 ? O2 Cu2 O10 92.69(12) . . ? O1 Cu2 O10 82.13(11) . . ? O6 Cu2 O10 166.88(12) 2_564 . ? O2 Cu2 O4 94.79(12) . . ? O1 Cu2 O4 95.75(11) . . ? O6 Cu2 O4 88.72(13) 2_564 . ? O10 Cu2 O4 80.19(12) . . ? O2 Cu2 O8 79.51(11) . . ? O1 Cu2 O8 90.53(11) . . ? O6 Cu2 O8 87.09(11) 2_564 . ? O10 Cu2 O8 104.66(9) . . ? O4 Cu2 O8 172.58(11) . . ? O1 Cu3 O3 94.21(12) . . ? O1 Cu3 O9 176.20(13) . . ? O3 Cu3 O9 88.78(12) . . ? O1 Cu3 O2 83.25(11) . 2_565 ? O3 Cu3 O2 172.27(13) . 2_565 ? O9 Cu3 O2 93.49(12) . 2_565 ? O1 Cu3 Cu1 41.60(8) . . ? O3 Cu3 Cu1 134.82(9) . . ? O9 Cu3 Cu1 134.99(9) . . ? O2 Cu3 Cu1 41.77(8) 2_565 . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 74.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.672 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 946322' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cu N4 O8' _chemical_formula_weight 429.83 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' 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' Cu Cu -1.9646 0.5888 '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 7.1674(6) _cell_length_b 7.5711(8) _cell_length_c 8.4825(11) _cell_angle_alpha 109.937(11) _cell_angle_beta 94.919(8) _cell_angle_gamma 116.156(9) _cell_volume 372.90(7) _cell_formula_units_Z 1 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1721 _cell_measurement_theta_min 5.775 _cell_measurement_theta_max 73.758 _exptl_crystal_description 'thin plate' _exptl_crystal_colour blue _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.192 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 219 _exptl_absorpt_coefficient_mu 2.645 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.626 _exptl_absorpt_correction_T_max 0.900 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.2273 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2302 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.78 _diffrn_reflns_theta_max 73.92 _reflns_number_total 1447 _reflns_number_gt 1395 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1241P)^2^+7.9601P] 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 1447 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.3181 _refine_ls_wR_factor_gt 0.3175 _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 C1 C 0.2122(14) 0.4156(15) 0.0192(11) 0.0126(17) Uani 1 1 d . . . C2 C 0.1904(15) -0.1720(15) -0.2327(12) 0.0160(19) Uani 1 1 d . . . C3 C 0.3421(15) -0.2610(16) -0.2719(12) 0.0155(18) Uani 1 1 d . . . H3A H 0.4715 -0.1764 -0.1699 0.019 Uiso 1 1 calc R . . H3B H 0.2685 -0.4131 -0.2856 0.019 Uiso 1 1 calc R . . C4 C 0.3518(15) 0.6637(14) 0.1280(11) 0.0142(18) Uani 1 1 d . . . H4A H 0.4779 0.7218 0.0829 0.017 Uiso 1 1 calc R . . H4B H 0.2652 0.7323 0.1145 0.017 Uiso 1 1 calc R . . C5 C 0.6265(15) 0.7611(15) 0.3979(12) 0.0154(18) Uani 1 1 d . . . H5 H 0.7460 0.7767 0.3515 0.018 Uiso 1 1 calc R . . C6 C 0.6156(15) 0.7738(15) 0.5600(12) 0.0150(18) Uani 1 1 d . . . H6 H 0.7270 0.7993 0.6487 0.018 Uiso 1 1 calc R . . C7 C 0.3030(14) 0.7085(14) 0.4208(11) 0.0116(17) Uani 1 1 d . . . H7 H 0.1583 0.6797 0.3930 0.014 Uiso 1 1 calc R . . N1 N 0.4132(12) -0.2568(12) -0.4265(10) 0.0137(16) Uani 1 1 d . . . N2 N 0.4287(12) 0.7208(12) 0.3141(10) 0.0140(16) Uani 1 1 d . . . O1 O 0.2250(10) 0.3026(10) 0.0970(9) 0.0166(14) Uani 1 1 d . . . O2 O 0.2111(11) -0.0864(11) -0.0683(9) 0.0183(14) Uani 1 1 d . . . O3 O 0.0617(11) -0.1913(13) -0.3512(9) 0.0226(16) Uani 1 1 d . . . O4 O 0.1068(11) 0.3520(12) -0.1298(8) 0.0203(15) Uani 1 1 d . . . Cu1 Cu 0.0000 0.0000 0.0000 0.0102(6) Uani 1 2 d S . . 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 0.007(4) 0.019(4) 0.012(4) 0.007(3) 0.005(3) 0.006(3) C2 0.014(4) 0.015(4) 0.019(5) 0.008(4) 0.008(4) 0.007(4) C3 0.015(4) 0.022(5) 0.016(4) 0.009(4) 0.004(3) 0.014(4) C4 0.019(5) 0.014(4) 0.012(4) 0.008(4) 0.004(3) 0.008(4) C5 0.016(4) 0.019(4) 0.018(4) 0.010(4) 0.006(4) 0.012(4) C6 0.013(4) 0.017(4) 0.019(4) 0.008(4) 0.003(3) 0.010(4) C7 0.012(4) 0.011(4) 0.013(4) 0.008(3) 0.004(3) 0.006(3) N1 0.013(4) 0.018(4) 0.014(4) 0.007(3) 0.004(3) 0.011(3) N2 0.012(4) 0.015(4) 0.011(4) 0.006(3) 0.001(3) 0.005(3) O1 0.016(3) 0.016(3) 0.020(3) 0.008(3) 0.004(3) 0.010(3) O2 0.021(3) 0.017(3) 0.019(3) 0.006(3) 0.012(3) 0.011(3) O3 0.020(4) 0.041(4) 0.023(4) 0.020(3) 0.007(3) 0.023(3) O4 0.020(3) 0.026(4) 0.011(3) 0.006(3) 0.002(3) 0.010(3) Cu1 0.0101(10) 0.0091(9) 0.0118(10) 0.0044(7) 0.0031(7) 0.0051(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 C1 O4 1.225(11) . ? C1 O1 1.273(11) . ? C1 C4 1.543(12) . ? C2 O3 1.227(12) . ? C2 O2 1.285(12) . ? C2 C3 1.517(12) . ? C3 N1 1.453(12) . ? C4 N2 1.469(11) . ? C5 C6 1.357(13) . ? C5 N2 1.381(12) . ? C6 N1 1.386(12) 1_566 ? C7 N2 1.328(11) . ? C7 N1 1.334(11) 1_566 ? N1 C7 1.334(11) 1_544 ? N1 C6 1.386(12) 1_544 ? O1 Cu1 1.938(6) . ? O2 Cu1 1.954(6) . ? Cu1 O1 1.938(6) 2 ? Cu1 O2 1.954(6) 2 ? 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 O4 C1 O1 128.2(9) . . ? O4 C1 C4 117.0(8) . . ? O1 C1 C4 114.7(8) . . ? O3 C2 O2 126.9(9) . . ? O3 C2 C3 120.9(8) . . ? O2 C2 C3 112.2(8) . . ? N1 C3 C2 115.4(7) . . ? N2 C4 C1 111.9(7) . . ? C6 C5 N2 106.0(8) . . ? C5 C6 N1 107.9(8) . 1_566 ? N2 C7 N1 108.8(8) . 1_566 ? C7 N1 C6 107.8(7) 1_544 1_544 ? C7 N1 C3 129.1(8) 1_544 . ? C6 N1 C3 123.0(7) 1_544 . ? C7 N2 C5 109.5(8) . . ? C7 N2 C4 123.7(8) . . ? C5 N2 C4 126.2(8) . . ? C1 O1 Cu1 117.2(6) . . ? C2 O2 Cu1 116.8(6) . . ? O1 Cu1 O1 180.0(7) . 2 ? O1 Cu1 O2 90.2(3) . 2 ? O1 Cu1 O2 89.8(3) 2 2 ? O1 Cu1 O2 89.8(3) . . ? O1 Cu1 O2 90.2(3) 2 . ? O2 Cu1 O2 180.00(15) 2 . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 73.92 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 2.644 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.258 _database_code_depnum_ccdc_archive 'CCDC 946323' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H42 B Cu2 F4 N8 Na O23' _chemical_formula_weight 1095.58 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' B B 0.0090 0.0039 '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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.1353 0.1239 '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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P-42c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x, y, -z+1/2' 'x, -y, -z+1/2' '-y, -x, z+1/2' 'y, x, z+1/2' _cell_length_a 12.3883(3) _cell_length_b 12.3883(3) _cell_length_c 14.5923(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2239.48(10) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2087 _cell_measurement_theta_min 3.56 _cell_measurement_theta_max 74.11 _exptl_crystal_description 'elongated octahedron' _exptl_crystal_colour blue _exptl_crystal_size_max 0.2690 _exptl_crystal_size_mid 0.1437 _exptl_crystal_size_min 0.1091 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 2.236 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.450 _exptl_absorpt_correction_T_max 0.648 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.2273 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4291 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 67.99 _reflns_number_total 1805 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1180P)^2^+1.9128P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(8) _refine_ls_number_reflns 1805 _refine_ls_number_parameters 155 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Na1 Na 0.4803(7) 0.9784(6) 0.6835(6) 0.049(2) Uiso 0.25 1 d P . . O1WA O 0.3677(7) 0.8796(7) 0.5771(7) 0.054(2) Uiso 0.50 1 d P . . O1WB O 0.4099(16) 0.9122(15) 0.5841(16) 0.129(7) Uiso 0.50 1 d P . . O2WA O 0.6769(11) 1.012(2) 0.7409(19) 0.063(5) Uiso 0.25 1 d P . . O3W O 0.5000 0.8074(14) 0.7500 0.098(5) Uiso 0.50 2 d SP . . B1 B 1.0000 1.0000 0.7776(10) 0.075(6) Uiso 0.50 2 d SPD . . F1 F 0.9077(7) 1.0065(11) 0.7189(6) 0.098(3) Uiso 0.50 1 d PD . . F2 F 0.9959(10) 0.9024(7) 0.8279(6) 0.095(3) Uiso 0.50 1 d PD . . O4W O 1.0000 1.0000 0.919(2) 0.210(13) Uiso 0.50 2 d SP . . Cu1 Cu 0.5000 1.0000 0.2500 0.0281(3) Uani 1 4 d S . . Cu2 Cu 0.5000 0.5000 0.7500 0.0477(4) Uani 1 4 d S . . O4 O 0.3878(3) 0.8900(3) 0.2367(3) 0.0365(8) Uani 1 1 d . . . O1 O 0.3880(4) 0.4846(3) 0.6582(2) 0.0518(10) Uani 1 1 d . . . N2 N 0.2134(3) 0.7473(4) 0.3890(3) 0.0428(10) Uani 1 1 d . . . O3 O 0.3635(3) 0.9101(3) 0.3873(2) 0.0405(8) Uani 1 1 d . . . N1 N 0.2208(4) 0.6393(4) 0.5044(3) 0.0459(11) Uani 1 1 d . . . O2 O 0.3879(4) 0.6627(3) 0.6311(3) 0.0548(10) Uani 1 1 d . . . C7 C 0.3395(4) 0.8715(4) 0.3130(3) 0.0336(10) Uani 1 1 d . . . C3 C 0.2583(4) 0.6593(4) 0.4203(3) 0.0408(11) Uani 1 1 d . . . H3 H 0.3095 0.6163 0.3884 0.049 Uiso 1 1 calc R . . C6 C 0.2411(4) 0.7966(4) 0.3012(4) 0.0431(12) Uani 1 1 d . . . H6A H 0.1788 0.8387 0.2781 0.052 Uiso 1 1 calc R . . H6B H 0.2579 0.7396 0.2559 0.052 Uiso 1 1 calc R . . C1 C 0.3510(5) 0.5699(4) 0.6208(4) 0.0463(13) Uani 1 1 d . . . C2 C 0.2541(5) 0.5481(5) 0.5599(4) 0.0518(13) Uani 1 1 d . . . H2A H 0.2713 0.4869 0.5189 0.062 Uiso 1 1 calc R . . H2B H 0.1926 0.5259 0.5990 0.062 Uiso 1 1 calc R . . C5 C 0.1419(6) 0.7843(6) 0.4533(5) 0.0683(19) Uani 1 1 d . . . H5 H 0.0977 0.8466 0.4479 0.082 Uiso 1 1 calc R . . C4 C 0.1453(7) 0.7161(6) 0.5263(5) 0.070(2) Uani 1 1 d . . . H4 H 0.1041 0.7206 0.5810 0.084 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 0.0314(6) 0.0298(6) 0.0231(6) 0.000 0.000 0.000 Cu2 0.0819(11) 0.0323(7) 0.0288(6) 0.000 0.000 0.000 O4 0.0358(15) 0.0366(15) 0.037(2) 0.0012(15) 0.0053(15) -0.0070(13) O1 0.086(3) 0.038(2) 0.0318(16) 0.0024(16) -0.0046(17) -0.002(2) N2 0.033(2) 0.051(2) 0.044(2) 0.005(2) 0.0053(18) -0.006(2) O3 0.044(2) 0.050(2) 0.0282(16) 0.0064(15) -0.0028(15) -0.0034(16) N1 0.051(3) 0.043(2) 0.044(2) 0.005(2) 0.013(2) -0.004(2) O2 0.069(3) 0.045(2) 0.051(2) 0.0030(18) 0.000(2) -0.0049(19) C7 0.030(2) 0.036(2) 0.034(2) 0.007(2) -0.0006(19) -0.0021(19) C3 0.042(3) 0.048(3) 0.032(2) 0.004(2) 0.003(2) -0.004(2) C6 0.041(3) 0.048(3) 0.040(3) 0.010(2) 0.000(2) -0.013(3) C1 0.067(4) 0.039(3) 0.033(2) 0.003(2) 0.007(3) 0.001(3) C2 0.063(3) 0.051(3) 0.042(3) 0.010(2) 0.003(3) -0.007(3) C5 0.071(4) 0.070(4) 0.063(4) 0.022(3) 0.022(4) 0.019(4) C4 0.072(4) 0.076(5) 0.063(4) 0.024(4) 0.030(4) 0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 Na1 0.724(16) 2_675 ? Na1 O1WB 1.88(2) . ? Na1 Na1 2.002(17) 5_656 ? Na1 Na1 2.014(17) 6_576 ? Na1 O2WA 2.124(19) 2_675 ? Na1 O2WA 2.28(2) 5_656 ? Na1 O3W 2.343(18) . ? Na1 O1WB 2.41(2) 2_675 ? Na1 O1WA 2.420(13) . ? Na1 O2WA 2.610(18) . ? Na1 O2WA 2.676(19) 6_576 ? Na1 O3W 2.836(18) 2_675 ? O1WA O1WB 0.67(2) . ? O1WA Na1 3.009(13) 2_675 ? O1WB Na1 2.41(2) 2_675 ? O2WA O2WA 0.40(6) 6_576 ? O2WA Na1 2.124(19) 2_675 ? O2WA Na1 2.28(2) 5_656 ? O2WA Na1 2.676(19) 6_576 ? O3W Na1 2.343(18) 5_656 ? O3W Na1 2.836(18) 6_576 ? O3W Na1 2.836(18) 2_675 ? B1 B1 0.80(3) 5_756 ? B1 F1 1.148(8) 6_576 ? B1 F1 1.148(8) 5_756 ? B1 F2 1.416(8) 2_775 ? B1 F2 1.416(8) . ? B1 F1 1.431(8) . ? B1 F1 1.431(8) 2_775 ? B1 F2 1.958(16) 6_576 ? B1 F2 1.958(16) 5_756 ? F1 F1 0.921(16) 6_576 ? F1 B1 1.148(8) 5_756 ? F1 F2 1.714(17) 6_576 ? F2 F1 1.714(16) 6_576 ? F2 O4W 1.80(3) . ? F2 B1 1.958(16) 5_756 ? O4W F2 1.80(3) 2_775 ? Cu1 O4 1.956(3) 2_675 ? Cu1 O4 1.956(3) . ? Cu1 O4 1.956(3) 6_575 ? Cu1 O4 1.956(3) 5_655 ? Cu2 O1 1.938(4) . ? Cu2 O1 1.938(4) 2_665 ? Cu2 O1 1.938(4) 6_566 ? Cu2 O1 1.938(4) 5_656 ? O4 C7 1.284(6) . ? O1 C1 1.274(7) . ? N2 C3 1.307(7) . ? N2 C5 1.369(8) . ? N2 C6 1.460(6) . ? O3 C7 1.222(6) . ? N1 C3 1.334(7) . ? N1 C4 1.372(10) . ? N1 C2 1.450(7) . ? O2 C1 1.246(7) . ? C7 C6 1.541(7) . ? C1 C2 1.518(8) . ? C5 C4 1.360(9) . ? 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 Na1 Na1 O1WB 129.4(8) 2_675 . ? Na1 Na1 Na1 80.5(5) 2_675 5_656 ? O1WB Na1 Na1 149.4(8) . 5_656 ? Na1 Na1 Na1 78.7(5) 2_675 6_576 ? O1WB Na1 Na1 149.2(8) . 6_576 ? Na1 Na1 Na1 20.8(5) 5_656 6_576 ? Na1 Na1 O2WA 125.3(14) 2_675 2_675 ? O1WB Na1 O2WA 84.4(10) . 2_675 ? Na1 Na1 O2WA 80.8(9) 5_656 2_675 ? Na1 Na1 O2WA 66.8(8) 6_576 2_675 ? Na1 Na1 O2WA 116.1(13) 2_675 5_656 ? O1WB Na1 O2WA 93.3(10) . 5_656 ? Na1 Na1 O2WA 74.8(8) 5_656 5_656 ? Na1 Na1 O2WA 58.9(7) 6_576 5_656 ? O2WA Na1 O2WA 9.8(13) 2_675 5_656 ? Na1 Na1 O3W 126.7(12) 2_675 . ? O1WB Na1 O3W 88.5(7) . . ? Na1 Na1 O3W 64.7(3) 5_656 . ? Na1 Na1 O3W 80.8(5) 6_576 . ? O2WA Na1 O3W 88.9(8) 2_675 . ? O2WA Na1 O3W 93.2(7) 5_656 . ? Na1 Na1 O1WB 37.1(6) 2_675 2_675 ? O1WB Na1 O1WB 92.5(13) . 2_675 ? Na1 Na1 O1WB 116.5(7) 5_656 2_675 ? Na1 Na1 O1WB 115.6(7) 6_576 2_675 ? O2WA Na1 O1WB 136.6(9) 2_675 2_675 ? O2WA Na1 O1WB 132.2(9) 5_656 2_675 ? O3W Na1 O1WB 134.4(5) . 2_675 ? Na1 Na1 O1WA 139.7(4) 2_675 . ? O1WB Na1 O1WA 10.6(8) . . ? Na1 Na1 O1WA 139.7(5) 5_656 . ? Na1 Na1 O1WA 138.8(4) 6_576 . ? O2WA Na1 O1WA 75.6(8) 2_675 . ? O2WA Na1 O1WA 84.9(7) 5_656 . ? O3W Na1 O1WA 82.4(4) . . ? O1WB Na1 O1WA 103.0(6) 2_675 . ? Na1 Na1 O2WA 41.6(12) 2_675 . ? O1WB Na1 O2WA 138.7(9) . . ? Na1 Na1 O2WA 57.4(7) 5_656 . ? Na1 Na1 O2WA 69.4(6) 6_576 . ? O2WA Na1 O2WA 136.1(13) 2_675 . ? O2WA Na1 O2WA 127.8(6) 5_656 . ? O3W Na1 O2WA 85.1(7) . . ? O1WB Na1 O2WA 64.9(8) 2_675 . ? O1WA Na1 O2WA 145.6(7) . . ? Na1 Na1 O2WA 49.8(11) 2_675 6_576 ? O1WB Na1 O2WA 139.4(9) . 6_576 ? Na1 Na1 O2WA 51.6(7) 5_656 6_576 ? Na1 Na1 O2WA 65.9(6) 6_576 6_576 ? O2WA Na1 O2WA 132.1(5) 2_675 6_576 ? O2WA Na1 O2WA 124.8(12) 5_656 6_576 ? O3W Na1 O2WA 76.9(6) . 6_576 ? O1WB Na1 O2WA 73.1(8) 2_675 6_576 ? O1WA Na1 O2WA 144.2(7) . 6_576 ? O2WA Na1 O2WA 8.7(12) . 6_576 ? Na1 Na1 O3W 41.5(10) 2_675 2_675 ? O1WB Na1 O3W 135.4(7) . 2_675 ? Na1 Na1 O3W 69.3(2) 5_656 2_675 ? Na1 Na1 O3W 54.7(4) 6_576 2_675 ? O2WA Na1 O3W 83.9(8) 2_675 2_675 ? O2WA Na1 O3W 74.6(7) 5_656 2_675 ? O3W Na1 O3W 134.0(5) . 2_675 ? O1WB Na1 O3W 68.3(5) 2_675 2_675 ? O1WA Na1 O3W 138.0(4) . 2_675 ? O2WA Na1 O3W 70.1(6) . 2_675 ? O2WA Na1 O3W 75.0(6) 6_576 2_675 ? O1WB O1WA Na1 31(2) . . ? O1WB O1WA Na1 23(2) . 2_675 ? Na1 O1WA Na1 9.0(2) . 2_675 ? O1WA O1WB Na1 138(3) . . ? O1WA O1WB Na1 151(3) . 2_675 ? Na1 O1WB Na1 13.4(4) . 2_675 ? O2WA O2WA Na1 107(2) 6_576 2_675 ? O2WA O2WA Na1 63(2) 6_576 5_656 ? Na1 O2WA Na1 54.3(5) 2_675 5_656 ? O2WA O2WA Na1 95(3) 6_576 . ? Na1 O2WA Na1 13.1(4) 2_675 . ? Na1 O2WA Na1 47.8(4) 5_656 . ? O2WA O2WA Na1 76(3) 6_576 6_576 ? Na1 O2WA Na1 47.6(5) 2_675 6_576 ? Na1 O2WA Na1 14.1(4) 5_656 6_576 ? Na1 O2WA Na1 44.8(4) . 6_576 ? Na1 O3W Na1 50.6(6) 5_656 . ? Na1 O3W Na1 11.8(4) 5_656 6_576 ? Na1 O3W Na1 44.5(5) . 6_576 ? Na1 O3W Na1 44.5(5) 5_656 2_675 ? Na1 O3W Na1 11.8(4) . 2_675 ? Na1 O3W Na1 41.3(4) 6_576 2_675 ? B1 B1 F1 92.5(9) 5_756 6_576 ? B1 B1 F1 92.5(9) 5_756 5_756 ? F1 B1 F1 174.9(19) 6_576 5_756 ? B1 B1 F2 121.2(6) 5_756 2_775 ? F1 B1 F2 94.1(11) 6_576 2_775 ? F1 B1 F2 83.2(10) 5_756 2_775 ? B1 B1 F2 121.2(6) 5_756 . ? F1 B1 F2 83.2(10) 6_576 . ? F1 B1 F2 94.1(11) 5_756 . ? F2 B1 F2 117.5(13) 2_775 . ? B1 B1 F1 53.3(6) 5_756 . ? F1 B1 F1 40.0(8) 6_576 . ? F1 B1 F1 145.0(13) 5_756 . ? F2 B1 F1 106.9(6) 2_775 . ? F2 B1 F1 109.2(6) . . ? B1 B1 F1 53.3(6) 5_756 2_775 ? F1 B1 F1 145.0(13) 6_576 2_775 ? F1 B1 F1 40.0(8) 5_756 2_775 ? F2 B1 F1 109.2(6) 2_775 2_775 ? F2 B1 F1 106.9(6) . 2_775 ? F1 B1 F1 106.5(11) . 2_775 ? B1 B1 F2 38.2(4) 5_756 6_576 ? F1 B1 F2 93.0(8) 6_576 6_576 ? F1 B1 F2 91.0(9) 5_756 6_576 ? F2 B1 F2 83.2(7) 2_775 6_576 ? F2 B1 F2 159.1(7) . 6_576 ? F1 B1 F2 58.3(7) . 6_576 ? F1 B1 F2 65.5(8) 2_775 6_576 ? B1 B1 F2 38.2(4) 5_756 5_756 ? F1 B1 F2 91.0(9) 6_576 5_756 ? F1 B1 F2 93.0(8) 5_756 5_756 ? F2 B1 F2 159.1(7) 2_775 5_756 ? F2 B1 F2 83.2(7) . 5_756 ? F1 B1 F2 65.5(8) . 5_756 ? F1 B1 F2 58.3(7) 2_775 5_756 ? F2 B1 F2 76.4(7) 6_576 5_756 ? F1 F1 B1 86.8(9) 6_576 5_756 ? F1 F1 B1 53.2(6) 6_576 . ? B1 F1 B1 34.2(13) 5_756 . ? F1 F1 F2 120.5(15) 6_576 6_576 ? B1 F1 F2 55.1(7) 5_756 6_576 ? B1 F1 F2 76.4(8) . 6_576 ? B1 F2 F1 41.7(5) . 6_576 ? B1 F2 O4W 79.0(11) . . ? F1 F2 O4W 82.5(8) 6_576 . ? B1 F2 B1 20.6(7) . 5_756 ? F1 F2 B1 45.2(3) 6_576 5_756 ? O4W F2 B1 99.5(9) . 5_756 ? F2 O4W F2 84.6(16) 2_775 . ? O4 Cu1 O4 168.6(2) 2_675 . ? O4 Cu1 O4 91.69(18) 2_675 6_575 ? O4 Cu1 O4 89.43(18) . 6_575 ? O4 Cu1 O4 89.43(18) 2_675 5_655 ? O4 Cu1 O4 91.69(18) . 5_655 ? O4 Cu1 O4 168.6(2) 6_575 5_655 ? O1 Cu2 O1 92.5(2) . 2_665 ? O1 Cu2 O1 88.6(2) . 6_566 ? O1 Cu2 O1 168.7(2) 2_665 6_566 ? O1 Cu2 O1 168.7(2) . 5_656 ? O1 Cu2 O1 88.6(2) 2_665 5_656 ? O1 Cu2 O1 92.5(2) 6_566 5_656 ? C7 O4 Cu1 111.7(3) . . ? C1 O1 Cu2 118.2(4) . . ? C3 N2 C5 108.4(5) . . ? C3 N2 C6 123.8(5) . . ? C5 N2 C6 127.8(5) . . ? C3 N1 C4 108.8(5) . . ? C3 N1 C2 124.0(5) . . ? C4 N1 C2 127.1(5) . . ? O3 C7 O4 125.8(4) . . ? O3 C7 C6 121.8(4) . . ? O4 C7 C6 112.3(4) . . ? N2 C3 N1 109.2(5) . . ? N2 C6 C7 109.9(4) . . ? O2 C1 O1 125.5(6) . . ? O2 C1 C2 121.7(5) . . ? O1 C1 C2 112.8(5) . . ? N1 C2 C1 114.4(5) . . ? C4 C5 N2 107.9(6) . . ? C5 C4 N1 105.6(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.811 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 946324'