# 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Li O6' _chemical_formula_weight 258.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0959(4) _cell_length_b 18.7760(10) _cell_length_c 7.9719(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.190(3) _cell_angle_gamma 90.00 _cell_volume 1129.86(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5406 _cell_measurement_theta_min 2.6983 _cell_measurement_theta_max 28.3300 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9762 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details 'SADABS V 2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10739 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2814 _reflns_number_gt 2221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+0.2167P] 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 2814 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Li1 Li 0.2703(3) 1.02603(12) 0.6961(4) 0.0340(5) Uani 1 1 d . . . O1 O 0.25966(13) 0.91866(4) 0.68533(15) 0.0339(3) Uani 1 1 d . . . O1W O 0.14683(15) 1.05386(6) 0.45334(15) 0.0426(3) Uani 1 1 d . . . H1WA H 0.1591 1.0281 0.3617 0.064 Uiso 1 1 d . . . H1WB H 0.0513 1.0757 0.4073 0.064 Uiso 1 1 d . . . O2 O 0.54715(13) 0.90021(5) 0.76303(18) 0.0477(3) Uani 1 1 d . . . H2 H 0.5484 0.9439 0.7651 0.057 Uiso 1 1 calc R . . O2W O 0.16200(15) 1.05894(7) 0.85632(15) 0.0465(3) Uani 1 1 d . . . H2WA H 0.0524 1.0615 0.8409 0.070 Uiso 1 1 d . . . H2WB H 0.2184 1.0703 0.9627 0.070 Uiso 1 1 d . . . O3 O 0.19560(14) 0.54056(5) 0.70364(17) 0.0422(3) Uani 1 1 d . . . O4 O 0.47541(14) 0.53513(5) 0.73056(16) 0.0400(3) Uani 1 1 d . . . C1 C 0.20416(15) 0.68915(6) 0.56741(16) 0.0219(3) Uani 1 1 d . . . C2 C 0.21539(16) 0.76540(6) 0.56973(16) 0.0217(3) Uani 1 1 d . . . C3 C 0.07863(17) 0.80402(6) 0.43851(18) 0.0271(3) Uani 1 1 d . . . H3A H 0.0860 0.8534 0.4354 0.033 Uiso 1 1 calc R . . C4 C -0.06306(18) 0.77043(7) 0.31710(19) 0.0318(3) Uani 1 1 d . . . H4A H -0.1527 0.7970 0.2344 0.038 Uiso 1 1 calc R . . C5 C -0.07474(18) 0.69597(7) 0.31597(19) 0.0317(3) Uani 1 1 d . . . H5A H -0.1724 0.6733 0.2330 0.038 Uiso 1 1 calc R . . C6 C 0.05635(17) 0.65665(7) 0.43595(18) 0.0273(3) Uani 1 1 d . . . H6A H 0.0484 0.6072 0.4313 0.033 Uiso 1 1 calc R . . C7 C 0.34402(16) 0.64936(6) 0.69345(17) 0.0239(3) Uani 1 1 d . . . C8 C 0.48945(17) 0.68339(6) 0.81066(19) 0.0283(3) Uani 1 1 d . . . H8A H 0.5821 0.6567 0.8891 0.034 Uiso 1 1 calc R . . C9 C 0.50063(18) 0.75815(6) 0.81410(19) 0.0285(3) Uani 1 1 d . . . H9A H 0.6000 0.7804 0.8954 0.034 Uiso 1 1 calc R . . C10 C 0.36632(16) 0.79853(6) 0.69871(17) 0.0239(3) Uani 1 1 d . . . C11 C 0.38346(17) 0.87767(6) 0.71377(18) 0.0262(3) Uani 1 1 d . . . C12 C 0.33534(17) 0.56946(6) 0.70911(18) 0.0270(3) 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 Li1 0.0312(12) 0.0236(10) 0.0484(14) -0.0008(10) 0.0158(10) 0.0022(9) O1 0.0279(5) 0.0153(4) 0.0574(7) -0.0019(4) 0.0140(4) 0.0011(4) O1W 0.0471(7) 0.0370(6) 0.0426(6) 0.0019(4) 0.0149(5) 0.0123(5) O2 0.0276(5) 0.0155(4) 0.0950(10) -0.0018(5) 0.0161(6) -0.0023(4) O2W 0.0369(6) 0.0597(7) 0.0424(6) -0.0053(5) 0.0139(5) 0.0109(5) O3 0.0324(6) 0.0231(5) 0.0736(8) 0.0124(5) 0.0220(5) -0.0012(4) O4 0.0287(5) 0.0152(4) 0.0735(8) 0.0011(4) 0.0151(5) 0.0043(4) C1 0.0237(6) 0.0153(5) 0.0307(6) -0.0002(4) 0.0146(5) -0.0002(4) C2 0.0232(6) 0.0159(5) 0.0286(6) 0.0005(4) 0.0125(5) 0.0008(4) C3 0.0299(7) 0.0178(5) 0.0347(7) 0.0034(5) 0.0130(5) 0.0039(5) C4 0.0283(7) 0.0298(7) 0.0341(7) 0.0039(5) 0.0075(6) 0.0052(5) C5 0.0271(7) 0.0304(7) 0.0350(7) -0.0042(5) 0.0083(5) -0.0042(5) C6 0.0298(7) 0.0196(6) 0.0345(7) -0.0025(5) 0.0140(6) -0.0036(5) C7 0.0253(6) 0.0145(5) 0.0348(7) 0.0018(4) 0.0144(5) 0.0018(4) C8 0.0258(6) 0.0179(6) 0.0383(7) 0.0032(5) 0.0081(5) 0.0038(5) C9 0.0253(6) 0.0193(6) 0.0380(7) -0.0014(5) 0.0080(5) -0.0012(5) C10 0.0252(6) 0.0140(5) 0.0346(7) 0.0002(4) 0.0133(5) -0.0001(4) C11 0.0268(6) 0.0166(5) 0.0357(7) -0.0002(5) 0.0120(5) -0.0012(5) C12 0.0266(6) 0.0156(6) 0.0375(7) 0.0020(5) 0.0102(5) 0.0013(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 Li1 O2W 1.895(3) . ? Li1 O1W 1.903(3) . ? Li1 O4 1.934(3) 2_656 ? Li1 O1 2.018(2) . ? O1 C11 1.2182(16) . ? O1W H1WA 0.9110 . ? O1W H1WB 0.8342 . ? O2 C11 1.3089(16) . ? O2 H2 0.8200 . ? O2W H2WA 0.8520 . ? O2W H2WB 0.8326 . ? O3 C12 1.2413(16) . ? O4 C12 1.2612(16) . ? O4 Li1 1.934(3) 2_646 ? C1 C6 1.4129(17) . ? C1 C7 1.4238(17) . ? C1 C2 1.4343(15) . ? C2 C3 1.4173(17) . ? C2 C10 1.4244(17) . ? C3 C4 1.3593(19) . ? C3 H3A 0.9300 . ? C4 C5 1.4011(19) . ? C4 H4A 0.9300 . ? C5 C6 1.3611(19) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.3683(18) . ? C7 C12 1.5091(16) . ? C8 C9 1.4062(17) . ? C8 H8A 0.9300 . ? C9 C10 1.3713(18) . ? C9 H9A 0.9300 . ? C10 C11 1.4932(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2W Li1 O1W 113.28(13) . . ? O2W Li1 O4 117.96(14) . 2_656 ? O1W Li1 O4 113.17(14) . 2_656 ? O2W Li1 O1 109.37(13) . . ? O1W Li1 O1 103.43(12) . . ? O4 Li1 O1 97.20(11) 2_656 . ? C11 O1 Li1 127.13(11) . . ? Li1 O1W H1WA 120.0 . . ? Li1 O1W H1WB 130.2 . . ? H1WA O1W H1WB 105.1 . . ? C11 O2 H2 109.5 . . ? Li1 O2W H2WA 129.2 . . ? Li1 O2W H2WB 123.6 . . ? H2WA O2W H2WB 107.0 . . ? C12 O4 Li1 153.25(11) . 2_646 ? C6 C1 C7 122.76(11) . . ? C6 C1 C2 118.26(11) . . ? C7 C1 C2 118.95(11) . . ? C3 C2 C10 123.15(11) . . ? C3 C2 C1 118.18(11) . . ? C10 C2 C1 118.62(10) . . ? C4 C3 C2 121.41(11) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 120.34(12) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 120.21(12) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C1 121.54(12) . . ? C5 C6 H6A 119.2 . . ? C1 C6 H6A 119.2 . . ? C8 C7 C1 120.36(11) . . ? C8 C7 C12 117.52(11) . . ? C1 C7 C12 122.07(11) . . ? C7 C8 C9 120.85(11) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C10 C9 C8 120.60(12) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C2 120.53(11) . . ? C9 C10 C11 117.92(11) . . ? C2 C10 C11 121.54(11) . . ? O1 C11 O2 121.82(11) . . ? O1 C11 C10 124.57(11) . . ? O2 C11 C10 113.61(11) . . ? O3 C12 O4 123.01(11) . . ? O3 C12 C7 120.06(11) . . ? O4 C12 C7 116.93(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O3 0.91 1.90 2.7981(15) 168.7 4_575 O1W H1WB O1 0.83 2.36 3.1126(15) 151.1 3_576 O2 H2 O4 0.82 1.73 2.5416(13) 172.9 2_656 O2W H2WA O3 0.85 1.95 2.7800(16) 165.0 2_556 O2W H2WB O2 0.83 2.39 3.1899(17) 162.7 3_677 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.262 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 959223' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11.25 H9.75 N0.75 Na1.50 O3.75' _chemical_formula_weight 249.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 18.2186(6) _cell_length_b 18.2186(6) _cell_length_c 8.6880(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2497.36(14) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30397 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4135 _reflns_number_gt 2981 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0668P)^2^+0.2458P] 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 -0.5(4) _refine_ls_number_reflns 4135 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.059 _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 0.63835(6) 0.36356(6) 0.17632(13) 0.0390(3) Uani 1 1 d . . . Na2 Na 0.51105(6) 0.25908(7) 0.51172(14) 0.0404(3) Uani 1 1 d . . . O2 O 0.78050(12) 0.39047(11) 0.2666(2) 0.0406(5) Uani 1 1 d . . . C11 C 0.81851(15) 0.45941(15) 0.1940(3) 0.0354(5) Uani 1 1 d . . . C10 C 0.91269(15) 0.51320(15) 0.2252(3) 0.0331(5) Uani 1 1 d . . . C9 C 1.03583(15) 0.63697(15) 0.3415(3) 0.0328(5) Uani 1 1 d . . . C8 C 0.94699(16) 0.59041(16) 0.3077(3) 0.0354(6) Uani 1 1 d . . . O1 O 0.78413(13) 0.48498(13) 0.1022(3) 0.0544(6) Uani 1 1 d . . . C6 C 0.96565(17) 0.48575(18) 0.1732(4) 0.0442(6) Uani 1 1 d . . . H6A H 0.9436 0.4359 0.1165 0.053 Uiso 1 1 calc R . . C4 C 1.06715(18) 0.71423(18) 0.4249(4) 0.0509(8) Uani 1 1 d . . . H4A H 1.1247 0.7462 0.4472 0.061 Uiso 1 1 calc R . . C3 C 0.89489(18) 0.62207(19) 0.3624(5) 0.0600(9) Uani 1 1 d . . . H3A H 0.8369 0.5916 0.3436 0.072 Uiso 1 1 calc R . . O1S O 0.37096(17) 0.23216(19) 0.5071(4) 0.0793(8) Uani 1 1 d . . . C2 C 1.0139(2) 0.7418(2) 0.4722(6) 0.0793(14) Uani 1 1 d . . . H2A H 1.0356 0.7925 0.5263 0.095 Uiso 1 1 calc R . . N1S N 0.2891(2) 0.2879(2) 0.5783(4) 0.0768(10) Uani 1 1 d . . . C1S C 0.3585(3) 0.2890(3) 0.5389(6) 0.0831(12) Uani 1 1 d . . . H1SA H 0.4063 0.3427 0.5349 0.100 Uiso 1 1 calc R . . C1 C 0.9277(2) 0.6953(3) 0.4410(7) 0.0898(16) Uani 1 1 d . . . H1A H 0.8923 0.7151 0.4748 0.108 Uiso 1 1 calc R . . C2S C 0.2817(5) 0.3604(5) 0.6070(9) 0.146(3) Uani 1 1 d . . . H2SA H 0.2558 0.3550 0.7058 0.220 Uiso 1 1 calc R . . H2SB H 0.2473 0.3654 0.5286 0.220 Uiso 1 1 calc R . . H2SC H 0.3370 0.4101 0.6062 0.220 Uiso 1 1 calc R . . C3S C 0.2182(5) 0.2120(6) 0.602(2) 0.297(9) Uani 1 1 d . . . H3SA H 0.1812 0.2191 0.6717 0.445 Uiso 1 1 calc R . . H3SB H 0.2335 0.1731 0.6460 0.445 Uiso 1 1 calc R . . H3SC H 0.1896 0.1900 0.5060 0.445 Uiso 1 1 calc R . . C5 C 1.05213(18) 0.53159(18) 0.2040(3) 0.0428(6) Uani 1 1 d . . . H5A H 1.0865 0.5117 0.1653 0.051 Uiso 1 1 calc R . . C7 C 1.08883(15) 0.60468(16) 0.2889(3) 0.0306(5) Uani 1 1 d . . . C12 C 1.18162(15) 0.64328(15) 0.3284(3) 0.0323(5) Uani 1 1 d . . . O4 O 1.22335(12) 0.61764(12) 0.2525(2) 0.0407(5) Uani 1 1 d . . . O3 O 1.21330(12) 0.69580(14) 0.4344(3) 0.0529(6) 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 Na1 0.0395(5) 0.0387(5) 0.0346(5) -0.0040(4) -0.0049(4) 0.0164(4) Na2 0.0406(5) 0.0417(6) 0.0409(5) -0.0058(5) 0.0013(5) 0.0220(5) O2 0.0360(10) 0.0334(10) 0.0427(11) 0.0056(8) 0.0035(9) 0.0100(8) C11 0.0311(12) 0.0324(13) 0.0336(13) -0.0027(11) -0.0044(11) 0.0091(11) C10 0.0289(12) 0.0319(12) 0.0322(13) 0.0041(10) -0.0024(10) 0.0105(10) C9 0.0295(11) 0.0286(11) 0.0381(13) -0.0027(11) 0.0004(11) 0.0129(9) C8 0.0295(12) 0.0330(13) 0.0423(15) 0.0000(11) -0.0002(11) 0.0145(10) O1 0.0432(11) 0.0526(12) 0.0548(12) 0.0125(10) -0.0184(10) 0.0146(10) C6 0.0411(14) 0.0398(14) 0.0488(16) -0.0168(13) -0.0088(14) 0.0179(12) C4 0.0320(14) 0.0385(15) 0.078(2) -0.0176(15) -0.0038(14) 0.0142(12) C3 0.0294(13) 0.0483(17) 0.099(3) -0.0144(19) 0.0002(17) 0.0173(13) O1S 0.0716(17) 0.102(2) 0.0863(19) -0.0236(17) -0.0159(16) 0.0601(16) C2 0.0489(19) 0.057(2) 0.133(4) -0.048(2) -0.007(2) 0.0275(17) N1S 0.063(2) 0.098(3) 0.088(2) -0.004(2) -0.0027(17) 0.055(2) C1S 0.060(2) 0.091(3) 0.092(3) -0.015(3) -0.007(2) 0.033(2) C1 0.0447(19) 0.069(2) 0.161(4) -0.050(3) 0.000(2) 0.0323(18) C2S 0.174(6) 0.187(7) 0.156(6) -0.077(5) -0.058(5) 0.149(6) C3S 0.109(5) 0.202(9) 0.60(3) 0.185(13) 0.131(10) 0.093(6) C5 0.0374(14) 0.0465(15) 0.0483(16) -0.0142(13) -0.0038(12) 0.0238(12) C7 0.0293(12) 0.0336(13) 0.0286(12) -0.0008(9) 0.0001(10) 0.0153(10) C12 0.0328(12) 0.0351(13) 0.0315(13) 0.0011(11) -0.0017(11) 0.0189(11) O4 0.0349(10) 0.0521(11) 0.0411(11) -0.0045(9) 0.0012(8) 0.0262(9) O3 0.0431(11) 0.0658(13) 0.0562(13) -0.0284(11) -0.0212(10) 0.0320(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O4 2.262(2) 5_565 ? Na1 O2 2.285(2) 2_654 ? Na1 O4 2.445(2) 6_544 ? Na1 O2 2.508(2) . ? Na1 O1 2.547(2) . ? Na1 O3 2.635(2) 6_544 ? Na1 C12 2.878(3) 6_544 ? Na1 Na1 3.3087(9) 2_654 ? Na1 Na1 3.3087(9) 3_665 ? Na1 Na2 3.3800(15) 2_654 ? Na1 Na2 3.5958(16) 3_664 ? Na2 O3 2.302(2) 6_544 ? Na2 O1 2.341(2) 2_655 ? Na2 O1S 2.346(3) . ? Na2 O2 2.378(2) 3_665 ? Na2 O4 2.388(2) 5_565 ? Na2 Na1 3.3800(15) 3_665 ? Na2 Na1 3.5958(16) 2_655 ? O2 C11 1.259(3) . ? O2 Na1 2.285(2) 3_665 ? O2 Na2 2.378(2) 2_654 ? C11 O1 1.240(3) . ? C11 C10 1.515(3) . ? C10 C6 1.367(4) . ? C10 C8 1.415(4) . ? C9 C4 1.424(4) . ? C9 C8 1.433(4) . ? C9 C7 1.434(3) . ? C8 C3 1.417(4) . ? O1 Na2 2.341(2) 3_664 ? C6 C5 1.391(4) . ? C6 H6A 0.9300 . ? C4 C2 1.360(4) . ? C4 H4A 0.9300 . ? C3 C1 1.344(5) . ? C3 H3A 0.9300 . ? O1S C1S 1.198(5) . ? C2 C1 1.388(5) . ? C2 H2A 0.9300 . ? N1S C1S 1.300(5) . ? N1S C3S 1.356(9) . ? N1S C2S 1.416(6) . ? C1S H1SA 0.9300 . ? C1 H1A 0.9300 . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9600 . ? C2S H2SC 0.9600 . ? C3S H3SA 0.9600 . ? C3S H3SB 0.9600 . ? C3S H3SC 0.9600 . ? C5 C7 1.369(4) . ? C5 H5A 0.9300 . ? C7 C12 1.511(3) . ? C12 O3 1.242(3) . ? C12 O4 1.260(3) . ? C12 Na1 2.878(3) 5_665 ? O4 Na1 2.262(2) 6_654 ? O4 Na2 2.388(2) 6_654 ? O4 Na1 2.445(2) 5_665 ? O3 Na2 2.302(2) 5_665 ? O3 Na1 2.635(2) 5_665 ? 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 Na1 O2 136.49(8) 5_565 2_654 ? O4 Na1 O4 125.10(8) 5_565 6_544 ? O2 Na1 O4 87.80(8) 2_654 6_544 ? O4 Na1 O2 86.78(8) 5_565 . ? O2 Na1 O2 124.84(8) 2_654 . ? O4 Na1 O2 89.59(7) 6_544 . ? O4 Na1 O1 104.55(8) 5_565 . ? O2 Na1 O1 80.39(7) 2_654 . ? O4 Na1 O1 115.43(8) 6_544 . ? O2 Na1 O1 51.89(6) . . ? O4 Na1 O3 79.63(7) 5_565 6_544 ? O2 Na1 O3 109.69(8) 2_654 6_544 ? O4 Na1 O3 51.04(6) 6_544 6_544 ? O2 Na1 O3 110.70(8) . 6_544 ? O1 Na1 O3 160.94(8) . 6_544 ? O4 Na1 C12 103.78(8) 5_565 6_544 ? O2 Na1 C12 97.03(8) 2_654 6_544 ? O4 Na1 C12 25.77(7) 6_544 6_544 ? O2 Na1 C12 103.65(7) . 6_544 ? O1 Na1 C12 140.71(9) . 6_544 ? O3 Na1 C12 25.56(7) 6_544 6_544 ? O4 Na1 Na1 167.14(7) 5_565 2_654 ? O2 Na1 Na1 49.22(5) 2_654 2_654 ? O4 Na1 Na1 43.13(6) 6_544 2_654 ? O2 Na1 Na1 97.27(6) . 2_654 ? O1 Na1 Na1 87.42(6) . 2_654 ? O3 Na1 Na1 87.52(6) 6_544 2_654 ? C12 Na1 Na1 63.43(7) 6_544 2_654 ? O4 Na1 Na1 47.64(5) 5_565 3_665 ? O2 Na1 Na1 166.59(7) 2_654 3_665 ? O4 Na1 Na1 97.95(6) 6_544 3_665 ? O2 Na1 Na1 43.62(6) . 3_665 ? O1 Na1 Na1 86.20(6) . 3_665 ? O3 Na1 Na1 83.16(6) 6_544 3_665 ? C12 Na1 Na1 93.27(6) 6_544 3_665 ? Na1 Na1 Na1 130.48(5) 2_654 3_665 ? O4 Na1 Na2 110.78(6) 5_565 2_654 ? O2 Na1 Na2 112.72(6) 2_654 2_654 ? O4 Na1 Na2 44.94(5) 6_544 2_654 ? O2 Na1 Na2 44.66(5) . 2_654 ? O1 Na1 Na2 82.75(6) . 2_654 ? O3 Na1 Na2 78.44(6) 6_544 2_654 ? C12 Na1 Na2 61.93(5) 6_544 2_654 ? Na1 Na1 Na2 65.45(4) 2_654 2_654 ? Na1 Na1 Na2 65.03(4) 3_665 2_654 ? O4 Na1 Na2 134.24(6) 5_565 3_664 ? O2 Na1 Na2 40.50(5) 2_654 3_664 ? O4 Na1 Na2 100.01(6) 6_544 3_664 ? O2 Na1 Na2 86.25(5) . 3_664 ? O1 Na1 Na2 40.45(5) . 3_664 ? O3 Na1 Na2 144.23(6) 6_544 3_664 ? C12 Na1 Na2 121.82(6) 6_544 3_664 ? Na1 Na1 Na2 58.44(2) 2_654 3_664 ? Na1 Na1 Na2 126.19(5) 3_665 3_664 ? Na2 Na1 Na2 95.03(3) 2_654 3_664 ? O3 Na2 O1 173.09(9) 6_544 2_655 ? O3 Na2 O1S 98.95(10) 6_544 . ? O1 Na2 O1S 86.70(10) 2_655 . ? O3 Na2 O2 90.17(8) 6_544 3_665 ? O1 Na2 O2 82.94(8) 2_655 3_665 ? O1S Na2 O2 148.47(11) . 3_665 ? O3 Na2 O4 84.32(8) 6_544 5_565 ? O1 Na2 O4 96.75(8) 2_655 5_565 ? O1S Na2 O4 116.64(10) . 5_565 ? O2 Na2 O4 94.17(7) 3_665 5_565 ? O3 Na2 Na1 86.64(6) 6_544 3_665 ? O1 Na2 Na1 89.17(6) 2_655 3_665 ? O1S Na2 Na1 161.78(9) . 3_665 ? O2 Na2 Na1 47.85(5) 3_665 3_665 ? O4 Na2 Na1 46.32(5) 5_565 3_665 ? O3 Na2 Na1 128.34(7) 6_544 2_655 ? O1 Na2 Na1 44.91(5) 2_655 2_655 ? O1S Na2 Na1 127.72(9) . 2_655 ? O2 Na2 Na1 38.61(5) 3_665 2_655 ? O4 Na2 Na1 91.78(6) 5_565 2_655 ? Na1 Na2 Na1 56.53(2) 3_665 2_655 ? C11 O2 Na1 130.65(17) . 3_665 ? C11 O2 Na2 128.41(18) . 2_654 ? Na1 O2 Na2 100.89(8) 3_665 2_654 ? C11 O2 Na1 92.16(15) . . ? Na1 O2 Na1 87.17(7) 3_665 . ? Na2 O2 Na1 87.49(7) 2_654 . ? O1 C11 O2 124.6(2) . . ? O1 C11 C10 119.6(2) . . ? O2 C11 C10 115.8(2) . . ? C6 C10 C8 119.3(2) . . ? C6 C10 C11 118.8(2) . . ? C8 C10 C11 121.9(2) . . ? C4 C9 C8 117.7(2) . . ? C4 C9 C7 123.3(2) . . ? C8 C9 C7 119.0(2) . . ? C10 C8 C3 121.4(2) . . ? C10 C8 C9 119.9(2) . . ? C3 C8 C9 118.6(2) . . ? C11 O1 Na2 145.9(2) . 3_664 ? C11 O1 Na1 90.83(16) . . ? Na2 O1 Na1 94.64(8) 3_664 . ? C10 C6 C5 120.7(2) . . ? C10 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C2 C4 C9 120.8(3) . . ? C2 C4 H4A 119.6 . . ? C9 C4 H4A 119.6 . . ? C1 C3 C8 121.2(3) . . ? C1 C3 H3A 119.4 . . ? C8 C3 H3A 119.4 . . ? C1S O1S Na2 118.2(3) . . ? C4 C2 C1 120.9(3) . . ? C4 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C1S N1S C3S 118.6(5) . . ? C1S N1S C2S 125.3(5) . . ? C3S N1S C2S 116.0(6) . . ? O1S C1S N1S 130.6(5) . . ? O1S C1S H1SA 114.7 . . ? N1S C1S H1SA 114.7 . . ? C3 C1 C2 120.7(3) . . ? C3 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? N1S C2S H2SA 109.5 . . ? N1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? N1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? N1S C3S H3SA 109.5 . . ? N1S C3S H3SB 109.5 . . ? H3SA C3S H3SB 109.5 . . ? N1S C3S H3SC 109.5 . . ? H3SA C3S H3SC 109.5 . . ? H3SB C3S H3SC 109.5 . . ? C7 C5 C6 122.9(2) . . ? C7 C5 H5A 118.5 . . ? C6 C5 H5A 118.5 . . ? C5 C7 C9 118.0(2) . . ? C5 C7 C12 117.6(2) . . ? C9 C7 C12 124.3(2) . . ? O3 C12 O4 122.7(2) . . ? O3 C12 C7 120.5(2) . . ? O4 C12 C7 116.8(2) . . ? O3 C12 Na1 66.23(14) . 5_665 ? O4 C12 Na1 57.54(13) . 5_665 ? C7 C12 Na1 169.13(18) . 5_665 ? C12 O4 Na1 134.69(17) . 6_654 ? C12 O4 Na2 122.86(17) . 6_654 ? Na1 O4 Na2 102.07(8) 6_654 6_654 ? C12 O4 Na1 96.69(16) . 5_665 ? Na1 O4 Na1 89.23(7) 6_654 5_665 ? Na2 O4 Na1 88.74(7) 6_654 5_665 ? C12 O3 Na2 158.9(2) . 5_665 ? C12 O3 Na1 88.21(15) . 5_665 ? Na2 O3 Na1 93.93(7) 5_665 5_665 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.301 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 959382' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H17 Mg2 O11' _chemical_formula_weight 530.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_hall '-P 2ac 2n' 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 14.7579(2) _cell_length_b 30.9679(4) _cell_length_c 11.3786(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5200.26(13) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9948 _cell_measurement_theta_min 2.260 _cell_measurement_theta_max 26.784 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 47338 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.29 _reflns_number_total 6546 _reflns_number_gt 4325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvent molecules were highly disordered and were impossible to refine usingconventional discrete-atom models; thus the contribution of solvent electron density was removed by the SQUEEZE routine in PLATON. ; _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^)+(0.0926P)^2^+3.4676P] 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 6546 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1748 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Mg1 Mg 0.11565(6) 0.59092(3) 0.30361(7) 0.0210(2) Uani 1 1 d . . . Mg2 Mg -0.11159(5) 0.57304(3) 0.40849(7) 0.0200(2) Uani 1 1 d . . . O1 O 0.00445(12) 0.54873(6) 0.29703(15) 0.0240(4) Uani 1 1 d . . . O2 O 0.10818(14) 0.58754(8) 0.48320(17) 0.0417(6) Uani 1 1 d . . . O3 O 0.12471(13) 0.59239(7) 0.12603(16) 0.0323(5) Uani 1 1 d . . . O4 O 0.03443(14) 0.64312(6) 0.30346(19) 0.0367(5) Uani 1 1 d . . . O5 O -0.11322(13) 0.63185(6) 0.32621(18) 0.0306(5) Uani 1 1 d . . . O6 O -0.13640(12) 0.54073(7) 0.24641(18) 0.0339(5) Uani 1 1 d . . . O7 O -0.23948(13) 0.57911(8) 0.44771(18) 0.0396(5) Uani 1 1 d . . . O8 O -0.03446(13) 0.59587(7) 0.54030(17) 0.0346(5) Uani 1 1 d . . . O1W O 0.19189(13) 0.53185(7) 0.3119(2) 0.0436(6) Uani 1 1 d . . . H1WA H 0.2552 0.5356 0.3079 0.065 Uiso 1 1 d . . . H1WB H 0.2160 0.5454 0.3815 0.065 Uiso 1 1 d . . . O2W O -0.10304(15) 0.51211(7) 0.4932(2) 0.0415(6) Uani 1 1 d . . . H2WA H -0.1406 0.4929 0.5171 0.062 Uiso 1 1 d . . . H2WB H -0.0597 0.4945 0.4792 0.062 Uiso 1 1 d . . . O3W O 0.23083(14) 0.62834(8) 0.3189(2) 0.0454(6) Uani 1 1 d . . . H3WA H 0.2736 0.6320 0.2540 0.068 Uiso 1 1 d . . . H3WB H 0.2435 0.6492 0.3709 0.068 Uiso 1 1 d . . . C1 C -0.05369(17) 0.53644(8) 0.2227(2) 0.0225(6) Uani 1 1 d . . . C2 C 0.0489(2) 0.59441(9) 0.5596(2) 0.0275(6) Uani 1 1 d . . . C3 C 0.17852(17) 0.58924(8) 0.0419(2) 0.0216(5) Uani 1 1 d . . . C4 C 0.08238(19) 0.59896(10) 0.6846(2) 0.0282(6) Uani 1 1 d . . . C5 C 0.14399(17) 0.59606(9) -0.0811(2) 0.0225(6) Uani 1 1 d . . . C6 C -0.05693(18) 0.70451(9) 0.3157(2) 0.0257(6) Uani 1 1 d . . . C7 C -0.02573(17) 0.51760(9) 0.1077(2) 0.0228(6) Uani 1 1 d . . . C8 C -0.06266(18) 0.53439(9) 0.0048(2) 0.0266(6) Uani 1 1 d . . . C9 C -0.04515(18) 0.65634(9) 0.3150(2) 0.0254(6) Uani 1 1 d . . . C10 C -0.12023(19) 0.72690(9) 0.3881(3) 0.0316(7) Uani 1 1 d . . . C11 C 0.0745(2) 0.62562(10) -0.1124(2) 0.0339(7) Uani 1 1 d . . . C12 C 0.1516(2) 0.57267(11) 0.7175(3) 0.0381(8) Uani 1 1 d . . . H12A H 0.1797 0.5554 0.6613 0.046 Uiso 1 1 calc R . . C14 C 0.00316(19) 0.72755(9) 0.2475(3) 0.0315(7) Uani 1 1 d . . . H14A H 0.0445 0.7128 0.2006 0.038 Uiso 1 1 calc R . . C15 C 0.1812(2) 0.57103(11) -0.1663(3) 0.0375(8) Uani 1 1 d . . . H15A H 0.2279 0.5522 -0.1465 0.045 Uiso 1 1 calc R . . C17 C -0.0660(3) 0.53686(18) -0.2050(5) 0.0236(11) Uani 0.50 1 d P . . H17A H -0.0433 0.5262 -0.2787 0.028 Uiso 0.50 1 d P . . C18 C -0.1811(2) 0.70529(11) 0.4648(3) 0.0533(10) Uani 1 1 d . . . H18A H -0.1810 0.6753 0.4670 0.064 Uiso 1 1 calc R . . C19 C -0.1243(4) 0.5720(2) -0.2018(5) 0.0335(14) Uani 0.50 1 d P . . H19A H -0.1452 0.5842 -0.2713 0.040 Uiso 0.50 1 calc PR . . C20 C -0.0234(3) 0.65799(16) -0.2615(3) 0.0842(18) Uani 1 1 d . . . H20A H -0.0450 0.6591 -0.3382 0.101 Uiso 1 1 calc R . . C21 C 0.0370(3) 0.65568(13) -0.0307(3) 0.0618(12) Uani 1 1 d . . . H21A H 0.0559 0.6551 0.0472 0.074 Uiso 1 1 calc R . . C22 C -0.1515(4) 0.5890(2) -0.0933(6) 0.0371(14) Uani 0.50 1 d P . . H22A H -0.1912 0.6123 -0.0900 0.045 Uiso 0.50 1 calc PR . . C23 C -0.2388(3) 0.72712(13) 0.5347(4) 0.0783(15) Uani 1 1 d . . . H23A H -0.2788 0.7121 0.5830 0.094 Uiso 1 1 calc R . . C24 C -0.0250(4) 0.68470(18) -0.0650(4) 0.102(2) Uani 1 1 d . . . H24A H -0.0477 0.7043 -0.0107 0.122 Uiso 1 1 calc R . . C25 C -0.0561(4) 0.6860(2) -0.1807(4) 0.114(3) Uani 1 1 d . . . H25A H -0.0995 0.7062 -0.2025 0.137 Uiso 1 1 calc R . . C26 C -0.1187(4) 0.57077(19) 0.0080(5) 0.0274(12) Uani 0.50 1 d P . . H26A H -0.1341 0.5828 0.0801 0.033 Uiso 0.50 1 calc PR . . C27 C 0.0430(2) 0.62694(10) -0.2311(3) 0.0393(8) Uani 1 1 d . . . C28 C -0.03623(18) 0.51660(9) -0.1047(2) 0.0248(6) 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 Mg1 0.0193(4) 0.0280(5) 0.0158(4) -0.0007(4) 0.0004(3) 0.0015(4) Mg2 0.0188(4) 0.0241(5) 0.0170(4) -0.0022(3) 0.0005(3) 0.0021(4) O1 0.0235(9) 0.0304(10) 0.0180(9) -0.0070(8) 0.0018(7) -0.0035(8) O2 0.0335(11) 0.0742(17) 0.0173(10) -0.0059(10) -0.0024(9) 0.0050(11) O3 0.0328(11) 0.0472(13) 0.0170(10) 0.0011(9) 0.0024(8) 0.0003(9) O4 0.0339(11) 0.0265(11) 0.0498(14) 0.0026(9) 0.0112(10) 0.0046(9) O5 0.0297(10) 0.0233(10) 0.0387(12) 0.0037(9) -0.0071(9) -0.0008(8) O6 0.0184(9) 0.0512(13) 0.0323(11) -0.0204(10) 0.0054(8) -0.0032(9) O7 0.0239(10) 0.0641(15) 0.0309(11) 0.0031(11) 0.0107(9) 0.0099(10) O8 0.0312(11) 0.0526(13) 0.0198(10) -0.0044(9) -0.0059(8) 0.0020(10) O1W 0.0244(10) 0.0429(13) 0.0634(16) 0.0171(11) 0.0121(10) 0.0079(9) O2W 0.0471(13) 0.0316(12) 0.0457(14) 0.0105(10) 0.0091(11) 0.0040(10) O3W 0.0316(11) 0.0592(15) 0.0455(14) -0.0197(11) 0.0075(10) -0.0146(11) C1 0.0225(13) 0.0223(13) 0.0227(13) -0.0035(11) 0.0030(11) -0.0022(11) C2 0.0349(16) 0.0314(15) 0.0163(13) -0.0014(11) -0.0038(12) 0.0038(13) C3 0.0212(13) 0.0250(13) 0.0188(13) 0.0005(11) -0.0032(11) -0.0018(11) C4 0.0331(15) 0.0363(16) 0.0152(13) -0.0032(12) -0.0070(11) 0.0059(13) C5 0.0201(12) 0.0314(15) 0.0161(12) 0.0001(11) -0.0027(10) 0.0024(11) C6 0.0265(13) 0.0225(14) 0.0281(15) -0.0005(11) 0.0009(12) 0.0008(11) C7 0.0205(12) 0.0263(14) 0.0215(13) -0.0061(11) 0.0032(10) -0.0024(11) C8 0.0227(13) 0.0335(15) 0.0237(14) -0.0055(12) 0.0042(11) 0.0017(12) C9 0.0267(14) 0.0256(14) 0.0239(14) 0.0013(11) 0.0011(11) 0.0014(12) C10 0.0295(15) 0.0254(15) 0.0398(17) 0.0009(13) 0.0085(13) 0.0009(12) C11 0.0408(17) 0.0398(17) 0.0211(14) -0.0077(13) -0.0071(13) 0.0153(14) C12 0.0373(17) 0.057(2) 0.0197(14) -0.0115(14) -0.0040(13) 0.0165(16) C14 0.0353(15) 0.0269(14) 0.0323(16) -0.0018(12) 0.0125(13) 0.0038(13) C15 0.0386(17) 0.052(2) 0.0217(15) -0.0060(14) -0.0071(13) 0.0221(15) C17 0.019(2) 0.030(3) 0.021(3) -0.007(2) -0.001(2) -0.004(2) C18 0.062(2) 0.0256(17) 0.072(3) 0.0039(17) 0.037(2) -0.0036(16) C19 0.031(3) 0.039(3) 0.031(3) 0.002(3) -0.004(3) 0.003(3) C20 0.114(4) 0.103(4) 0.036(2) -0.028(2) -0.039(2) 0.076(3) C21 0.084(3) 0.075(3) 0.0264(17) -0.0238(18) -0.0190(18) 0.048(2) C22 0.035(3) 0.032(3) 0.045(4) 0.004(3) 0.000(3) 0.011(3) C23 0.083(3) 0.044(2) 0.108(4) 0.005(2) 0.068(3) -0.003(2) C24 0.146(5) 0.111(4) 0.048(3) -0.038(3) -0.036(3) 0.099(4) C25 0.151(5) 0.131(5) 0.061(3) -0.041(3) -0.049(3) 0.115(4) C26 0.025(3) 0.034(3) 0.023(3) -0.004(2) 0.007(2) 0.004(2) C27 0.0510(19) 0.0444(18) 0.0224(15) -0.0068(13) -0.0147(14) 0.0214(16) C28 0.0237(13) 0.0286(14) 0.0220(14) -0.0033(11) 0.0002(11) -0.0005(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mg1 O4 2.013(2) . ? Mg1 O3 2.025(2) . ? Mg1 O2 2.049(2) . ? Mg1 O3W 2.065(2) . ? Mg1 O1 2.0990(19) . ? Mg1 O1W 2.150(2) . ? Mg1 Mg2 3.6023(12) . ? Mg1 H1WB 2.2284 . ? Mg2 O7 1.949(2) . ? Mg2 O8 2.011(2) . ? Mg2 O5 2.048(2) . ? Mg2 O2W 2.123(2) . ? Mg2 O6 2.130(2) . ? Mg2 O1 2.2601(19) . ? Mg2 C1 2.546(3) . ? O1 C1 1.263(3) . ? O2 C2 1.252(3) . ? O3 C3 1.247(3) . ? O4 C9 1.251(3) . ? O5 C9 1.265(3) . ? O6 C1 1.257(3) . ? O7 C3 1.256(3) 6_556 ? O8 C2 1.250(3) . ? O1W H1WA 0.9425 . ? O1W H1WB 0.9648 . ? O2W H2WA 0.8575 . ? O2W H2WB 0.8552 . ? O3W H3WA 0.9777 . ? O3W H3WB 0.8974 . ? C1 C7 1.491(4) . ? C2 C4 1.512(4) . ? C3 O7 1.256(3) 6_656 ? C3 C5 1.505(4) . ? C4 C12 1.359(4) . ? C4 C27 1.417(4) 1_556 ? C5 C15 1.357(4) . ? C5 C11 1.420(4) . ? C6 C14 1.378(4) . ? C6 C10 1.425(4) . ? C6 C9 1.502(4) . ? C7 C8 1.392(4) . ? C7 C28 1.400(4) 5_565 ? C8 C26 1.398(6) . ? C8 C28 1.417(4) . ? C10 C18 1.420(4) . ? C10 C10 1.431(6) 7_575 ? C11 C21 1.426(4) . ? C11 C27 1.429(4) . ? C12 C15 1.394(4) 1_556 ? C12 H12A 0.9300 . ? C14 C14 1.390(6) 7_575 ? C14 H14A 0.9300 . ? C15 C12 1.394(4) 1_554 ? C15 H15A 0.9300 . ? C17 C28 1.375(6) . ? C17 C19 1.387(8) . ? C17 H17A 0.9613 . ? C18 C23 1.347(5) . ? C18 H18A 0.9300 . ? C19 C22 1.400(9) . ? C19 H19A 0.9300 . ? C20 C25 1.352(6) . ? C20 C27 1.416(5) . ? C20 H20A 0.9300 . ? C21 C24 1.341(5) . ? C21 H21A 0.9300 . ? C22 C26 1.371(8) . ? C22 H22A 0.9300 . ? C23 C23 1.417(8) 7_575 ? C23 H23A 0.9300 . ? C24 C25 1.395(6) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C27 C4 1.417(4) 1_554 ? C28 C7 1.400(4) 5_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 Mg1 O3 91.17(9) . . ? O4 Mg1 O2 90.56(10) . . ? O3 Mg1 O2 178.22(10) . . ? O4 Mg1 O3W 92.26(10) . . ? O3 Mg1 O3W 90.96(9) . . ? O2 Mg1 O3W 89.38(10) . . ? O4 Mg1 O1 91.97(8) . . ? O3 Mg1 O1 91.72(8) . . ? O2 Mg1 O1 87.81(8) . . ? O3W Mg1 O1 174.94(10) . . ? O4 Mg1 O1W 174.47(9) . . ? O3 Mg1 O1W 91.61(9) . . ? O2 Mg1 O1W 86.63(10) . . ? O3W Mg1 O1W 92.46(10) . . ? O1 Mg1 O1W 83.17(8) . . ? O4 Mg1 Mg2 64.49(6) . . ? O3 Mg1 Mg2 113.29(6) . . ? O2 Mg1 Mg2 67.15(6) . . ? O3W Mg1 Mg2 145.58(7) . . ? O1 Mg1 Mg2 35.74(5) . . ? O1W Mg1 Mg2 110.00(6) . . ? O4 Mg1 H1WB 154.7 . . ? O3 Mg1 H1WB 111.5 . . ? O2 Mg1 H1WB 66.8 . . ? O3W Mg1 H1WB 77.0 . . ? O1 Mg1 H1WB 98.1 . . ? O1W Mg1 H1WB 25.4 . . ? Mg2 Mg1 H1WB 112.9 . . ? O7 Mg2 O8 110.10(10) . . ? O7 Mg2 O5 90.43(9) . . ? O8 Mg2 O5 92.01(9) . . ? O7 Mg2 O2W 92.25(10) . . ? O8 Mg2 O2W 86.58(9) . . ? O5 Mg2 O2W 177.26(9) . . ? O7 Mg2 O6 94.42(9) . . ? O8 Mg2 O6 155.25(9) . . ? O5 Mg2 O6 91.14(9) . . ? O2W Mg2 O6 89.17(9) . . ? O7 Mg2 O1 153.45(9) . . ? O8 Mg2 O1 96.13(8) . . ? O5 Mg2 O1 92.79(8) . . ? O2W Mg2 O1 85.03(8) . . ? O6 Mg2 O1 59.19(7) . . ? O7 Mg2 C1 123.92(10) . . ? O8 Mg2 C1 125.85(9) . . ? O5 Mg2 C1 91.17(9) . . ? O2W Mg2 C1 87.76(9) . . ? O6 Mg2 C1 29.51(7) . . ? O1 Mg2 C1 29.72(7) . . ? O7 Mg2 Mg1 164.32(8) . . ? O8 Mg2 Mg1 70.50(6) . . ? O5 Mg2 Mg1 73.91(6) . . ? O2W Mg2 Mg1 103.39(7) . . ? O6 Mg2 Mg1 86.87(6) . . ? O1 Mg2 Mg1 32.85(5) . . ? C1 Mg2 Mg1 58.73(6) . . ? C1 O1 Mg1 137.94(17) . . ? C1 O1 Mg2 87.78(15) . . ? Mg1 O1 Mg2 111.41(8) . . ? C2 O2 Mg1 136.18(19) . . ? C3 O3 Mg1 143.66(18) . . ? C9 O4 Mg1 145.29(19) . . ? C9 O5 Mg2 124.74(17) . . ? C1 O6 Mg2 93.91(16) . . ? C3 O7 Mg2 168.3(2) 6_556 . ? C2 O8 Mg2 132.47(18) . . ? Mg1 O1W H1WA 114.3 . . ? Mg1 O1W H1WB 81.9 . . ? H1WA O1W H1WB 67.7 . . ? Mg2 O2W H2WA 136.3 . . ? Mg2 O2W H2WB 121.7 . . ? H2WA O2W H2WB 95.8 . . ? Mg1 O3W H3WA 122.2 . . ? Mg1 O3W H3WB 129.2 . . ? H3WA O3W H3WB 106.3 . . ? O6 C1 O1 119.0(2) . . ? O6 C1 C7 119.9(2) . . ? O1 C1 C7 121.1(2) . . ? O6 C1 Mg2 56.58(13) . . ? O1 C1 Mg2 62.50(13) . . ? C7 C1 Mg2 174.7(2) . . ? O8 C2 O2 124.9(2) . . ? O8 C2 C4 118.9(2) . . ? O2 C2 C4 116.1(2) . . ? O3 C3 O7 124.1(2) . 6_656 ? O3 C3 C5 119.2(2) . . ? O7 C3 C5 116.7(2) 6_656 . ? C12 C4 C27 119.2(2) . 1_556 ? C12 C4 C2 116.7(3) . . ? C27 C4 C2 124.0(2) 1_556 . ? C15 C5 C11 118.8(2) . . ? C15 C5 C3 116.6(2) . . ? C11 C5 C3 124.6(2) . . ? C14 C6 C10 119.7(3) . . ? C14 C6 C9 115.9(2) . . ? C10 C6 C9 124.2(2) . . ? C8 C7 C28 121.2(2) . 5_565 ? C8 C7 C1 118.9(2) . . ? C28 C7 C1 119.9(2) 5_565 . ? C7 C8 C26 120.7(3) . . ? C7 C8 C28 119.1(2) . . ? C26 C8 C28 119.9(3) . . ? O4 C9 O5 124.1(3) . . ? O4 C9 C6 115.7(2) . . ? O5 C9 C6 120.2(2) . . ? C18 C10 C6 122.7(3) . . ? C18 C10 C10 118.11(18) . 7_575 ? C6 C10 C10 119.11(16) . 7_575 ? C5 C11 C21 122.5(3) . . ? C5 C11 C27 119.3(3) . . ? C21 C11 C27 118.1(3) . . ? C4 C12 C15 121.3(3) . 1_556 ? C4 C12 H12A 119.4 . . ? C15 C12 H12A 119.4 1_556 . ? C6 C14 C14 121.20(16) . 7_575 ? C6 C14 H14A 119.4 . . ? C14 C14 H14A 119.4 7_575 . ? C5 C15 C12 122.0(3) . 1_554 ? C5 C15 H15A 119.0 . . ? C12 C15 H15A 119.0 1_554 . ? C28 C17 C19 122.2(5) . . ? C28 C17 H17A 117.1 . . ? C19 C17 H17A 120.6 . . ? C23 C18 C10 121.8(3) . . ? C23 C18 H18A 119.1 . . ? C10 C18 H18A 119.1 . . ? C17 C19 C22 119.7(5) . . ? C17 C19 H19A 120.1 . . ? C22 C19 H19A 120.1 . . ? C25 C20 C27 121.1(3) . . ? C25 C20 H20A 119.4 . . ? C27 C20 H20A 119.4 . . ? C24 C21 C11 120.8(3) . . ? C24 C21 H21A 119.6 . . ? C11 C21 H21A 119.6 . . ? C26 C22 C19 119.0(6) . . ? C26 C22 H22A 120.5 . . ? C19 C22 H22A 120.5 . . ? C18 C23 C23 120.1(2) . 7_575 ? C18 C23 H23A 119.9 . . ? C23 C23 H23A 119.9 7_575 . ? C21 C24 C25 121.2(4) . . ? C21 C24 H24A 119.4 . . ? C25 C24 H24A 119.4 . . ? C20 C25 C24 120.4(4) . . ? C20 C25 H25A 119.8 . . ? C24 C25 H25A 119.8 . . ? C22 C26 C8 121.2(5) . . ? C22 C26 H26A 119.4 . . ? C8 C26 H26A 119.4 . . ? C4 C27 C20 122.3(3) 1_554 . ? C4 C27 C11 119.3(3) 1_554 . ? C20 C27 C11 118.3(3) . . ? C17 C28 C7 122.2(3) . 5_565 ? C17 C28 C8 117.7(3) . . ? C7 C28 C8 119.7(2) 5_565 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O6 0.94 1.72 2.634(3) 161.7 6_656 O1W H1WB O2 0.96 2.36 2.881(3) 113.2 . O2W H2WA O1W 0.86 2.22 2.915(3) 137.5 5_566 O3W H3WA O5 0.98 1.90 2.834(3) 158.2 6_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.982 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 959383' ####################################################################### # # 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 'C15 H13 Ca N O5' _chemical_formula_weight 327.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.70170(10) _cell_length_b 14.3958(3) _cell_length_c 14.9405(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1441.40(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8397 _cell_measurement_theta_min 2.7266 _cell_measurement_theta_max 28.3477 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8747 _exptl_absorpt_correction_T_max 0.9139 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 12984 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3540 _reflns_number_gt 3261 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.1645P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.36(3) _refine_ls_number_reflns 3540 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca1 Ca 0.13673(5) 0.196138(19) 0.541930(18) 0.01725(8) Uani 1 1 d . . . O1 O 0.28126(18) 0.29547(8) 0.42152(7) 0.0239(3) Uani 1 1 d . . . O2 O -0.00807(18) 0.34347(8) 0.47472(8) 0.0244(3) Uani 1 1 d . . . O3 O 0.2828(2) 0.29948(10) 0.64109(9) 0.0395(3) Uani 1 1 d . . . O4 O 0.0076(2) 0.10870(10) 0.42411(9) 0.0395(4) Uani 1 1 d . . . C1 C 0.1368(3) 0.35090(10) 0.42122(10) 0.0196(3) Uani 1 1 d . . . C2 C 0.1344(3) 0.42701(10) 0.35208(10) 0.0209(3) Uani 1 1 d . . . C3 C 0.1353(4) 0.40216(11) 0.26444(11) 0.0329(4) Uani 1 1 d . . . H3A H 0.1466 0.3398 0.2488 0.039 Uiso 1 1 calc R . . C4 C 0.1194(4) 0.47014(13) 0.19694(12) 0.0372(5) Uani 1 1 d . . . H4A H 0.1087 0.4514 0.1375 0.045 Uiso 1 1 calc R . . C5 C 0.1191(3) 0.56227(11) 0.21649(11) 0.0245(3) Uani 1 1 d . . . C6 C 0.1275(3) 0.59147(11) 0.30747(11) 0.0236(3) Uani 1 1 d . . . C7 C 0.1278(3) 0.52249(11) 0.37633(10) 0.0238(3) Uani 1 1 d . . . C8 C 0.1313(4) 0.68656(12) 0.33362(13) 0.0393(5) Uani 1 1 d . . . H8A H 0.1351 0.7325 0.2899 0.047 Uiso 1 1 calc R . . C9 C 0.1295(6) 0.71117(14) 0.42088(16) 0.0716(9) Uani 1 1 d . . . H9A H 0.1313 0.7737 0.4364 0.086 Uiso 1 1 calc R . . C10 C 0.1250(7) 0.64334(15) 0.48849(16) 0.0817(11) Uani 1 1 d . . . H10A H 0.1216 0.6612 0.5483 0.098 Uiso 1 1 calc R . . C11 C 0.1254(5) 0.55133(13) 0.46656(13) 0.0506(6) Uani 1 1 d . . . H11A H 0.1242 0.5069 0.5118 0.061 Uiso 1 1 calc R . . C12 C 0.3914(3) 0.37012(12) 0.63829(11) 0.0285(4) Uani 1 1 d . . . O1S O 0.1347(3) 0.08026(12) 0.64603(13) 0.0639(5) Uani 1 1 d . . . C1S C 0.1345(7) 0.0199(3) 0.7038(4) 0.0391(11) Uani 0.542(5) 1 d P A 1 H1S H 0.1390 0.0376 0.7636 0.047 Uiso 0.542(5) 1 calc PR A 1 N1S N 0.1283(7) -0.0684(3) 0.6842(4) 0.0453(10) Uani 0.542(5) 1 d P A 1 C2S C 0.1401(14) -0.1436(5) 0.7529(5) 0.0486(17) Uani 0.542(5) 1 d P A 1 H2S1 H 0.1584 -0.1165 0.8111 0.073 Uiso 0.542(5) 1 calc PR A 1 H2S2 H 0.2508 -0.1836 0.7396 0.073 Uiso 0.542(5) 1 calc PR A 1 H2S3 H 0.0188 -0.1790 0.7523 0.073 Uiso 0.542(5) 1 calc PR A 1 C3S C 0.1259(10) -0.0976(4) 0.5934(3) 0.0717(17) Uani 0.542(5) 1 d P A 1 H3S1 H 0.0294 -0.1463 0.5860 0.108 Uiso 0.542(5) 1 calc PR A 1 H3S2 H 0.2556 -0.1202 0.5771 0.108 Uiso 0.542(5) 1 calc PR A 1 H3S3 H 0.0912 -0.0460 0.5558 0.108 Uiso 0.542(5) 1 calc PR A 1 C1S' C 0.1353(10) -0.0093(5) 0.6557(5) 0.0484(16) Uani 0.458(5) 1 d P A 2 H1S' H 0.1390 -0.0483 0.6061 0.058 Uiso 0.458(5) 1 calc PR A 2 N1S' N 0.1307(8) -0.0435(5) 0.7366(5) 0.0562(17) Uani 0.458(5) 1 d P A 2 C2S' C 0.119(3) -0.1380(10) 0.7507(12) 0.156(8) Uani 0.458(5) 1 d P A 2 H2S4 H 0.1152 -0.1695 0.6941 0.234 Uiso 0.458(5) 1 calc PR A 2 H2S5 H -0.0002 -0.1520 0.7838 0.234 Uiso 0.458(5) 1 calc PR A 2 H2S6 H 0.2334 -0.1583 0.7840 0.234 Uiso 0.458(5) 1 calc PR A 2 C3S' C 0.1245(12) 0.0161(7) 0.8151(5) 0.094(3) Uani 0.458(5) 1 d P A 2 H3S4 H 0.1107 0.0796 0.7966 0.141 Uiso 0.458(5) 1 calc PR A 2 H3S5 H 0.2458 0.0090 0.8486 0.141 Uiso 0.458(5) 1 calc PR A 2 H3S6 H 0.0130 -0.0010 0.8519 0.141 Uiso 0.458(5) 1 calc PR A 2 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 Ca1 0.01916(16) 0.01638(12) 0.01620(13) 0.00108(12) -0.00231(12) -0.00215(13) O1 0.0225(6) 0.0233(6) 0.0258(6) 0.0067(5) -0.0014(5) 0.0024(5) O2 0.0207(6) 0.0256(5) 0.0270(6) 0.0082(5) 0.0030(5) -0.0019(5) O3 0.0445(9) 0.0378(7) 0.0360(7) -0.0196(6) -0.0050(6) -0.0061(7) O4 0.0470(9) 0.0409(8) 0.0306(7) -0.0159(6) -0.0075(7) -0.0034(7) C1 0.0197(8) 0.0197(7) 0.0193(7) 0.0040(5) -0.0040(7) -0.0045(7) C2 0.0165(8) 0.0211(7) 0.0249(8) 0.0082(6) -0.0003(7) 0.0009(8) C3 0.0530(12) 0.0203(7) 0.0254(8) 0.0042(6) 0.0001(10) 0.0014(9) C4 0.0609(15) 0.0307(9) 0.0201(8) 0.0043(7) -0.0009(10) 0.0010(11) C5 0.0215(9) 0.0267(7) 0.0254(8) 0.0108(6) 0.0005(7) 0.0005(8) C6 0.0212(9) 0.0241(7) 0.0255(8) 0.0068(6) -0.0007(8) 0.0006(8) C7 0.0265(9) 0.0217(7) 0.0232(8) 0.0057(6) -0.0021(8) 0.0010(8) C8 0.0587(13) 0.0198(8) 0.0396(10) 0.0079(7) -0.0041(10) -0.0002(11) C9 0.145(3) 0.0231(10) 0.0465(12) -0.0030(9) -0.0074(18) 0.0034(15) C10 0.180(3) 0.0361(12) 0.0296(11) -0.0044(9) -0.0069(19) 0.0041(19) C11 0.0966(19) 0.0301(9) 0.0252(9) 0.0048(7) -0.0046(13) 0.0066(12) C12 0.0287(11) 0.0294(8) 0.0275(9) -0.0125(7) -0.0051(8) 0.0058(8) O1S 0.0343(9) 0.0694(11) 0.0879(13) 0.0573(10) 0.0031(10) 0.0026(10) C1S 0.020(2) 0.050(3) 0.047(3) 0.023(2) -0.001(2) -0.001(2) N1S 0.0287(19) 0.047(2) 0.060(3) 0.022(2) 0.000(2) 0.0017(19) C2S 0.028(4) 0.042(3) 0.075(4) 0.037(3) -0.002(3) -0.012(3) C3S 0.056(3) 0.089(4) 0.070(3) -0.016(3) -0.002(3) -0.002(4) C1S' 0.025(3) 0.067(4) 0.053(4) 0.029(3) -0.001(3) -0.001(3) N1S' 0.025(2) 0.076(4) 0.068(4) 0.046(3) 0.003(3) 0.004(3) C2S' 0.037(7) 0.130(10) 0.299(18) 0.161(11) -0.030(8) 0.012(6) C3S' 0.056(5) 0.160(8) 0.066(4) 0.021(5) 0.008(4) 0.039(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 Ca1 O1S 2.2808(14) . ? Ca1 O3 2.3167(13) . ? Ca1 O4 2.3305(13) . ? Ca1 O1 2.4471(13) 4_456 ? Ca1 O2 2.4604(12) 4_556 ? Ca1 O1 2.4939(11) . ? Ca1 O2 2.5394(11) . ? Ca1 C1 2.8663(14) . ? Ca1 Ca1 3.8991(3) 4_556 ? Ca1 Ca1 3.8991(3) 4_456 ? O1 C1 1.254(2) . ? O1 Ca1 2.4470(13) 4_556 ? O2 C1 1.262(2) . ? O2 Ca1 2.4604(12) 4_456 ? O3 C12 1.251(2) . ? O4 C12 1.252(2) 4_456 ? C1 C2 1.506(2) . ? C2 C3 1.357(2) . ? C2 C7 1.422(2) . ? C3 C4 1.409(2) . ? C3 H3A 0.9300 . ? C4 C5 1.358(2) . ? C4 H4A 0.9300 . ? C5 C6 1.424(2) . ? C5 C12 1.522(2) 2_564 ? C6 C8 1.424(2) . ? C6 C7 1.430(2) . ? C7 C11 1.411(2) . ? C8 C9 1.351(3) . ? C8 H8A 0.9300 . ? C9 C10 1.405(3) . ? C9 H9A 0.9300 . ? C10 C11 1.364(3) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 O4 1.252(2) 4_556 ? C12 C5 1.522(2) 2_565 ? O1S C1S 1.224(5) . ? O1S C1S' 1.297(8) . ? C1S N1S 1.306(7) . ? C1S H1S 0.9300 . ? N1S C3S 1.420(7) . ? N1S C2S 1.494(9) . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C3S H3S1 0.9600 . ? C3S H3S2 0.9600 . ? C3S H3S3 0.9600 . ? C1S' N1S' 1.306(8) . ? C1S' H1S' 0.9300 . ? N1S' C2S' 1.378(15) . ? N1S' C3S' 1.453(11) . ? C2S' H2S4 0.9600 . ? C2S' H2S5 0.9600 . ? C2S' H2S6 0.9600 . ? C3S' H3S4 0.9600 . ? C3S' H3S5 0.9600 . ? C3S' H3S6 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 O1S Ca1 O3 92.07(7) . . ? O1S Ca1 O4 96.76(7) . . ? O3 Ca1 O4 170.67(6) . . ? O1S Ca1 O1 82.99(6) . 4_456 ? O3 Ca1 O1 103.71(5) . 4_456 ? O4 Ca1 O1 80.43(5) . 4_456 ? O1S Ca1 O2 84.57(6) . 4_556 ? O3 Ca1 O2 78.73(5) . 4_556 ? O4 Ca1 O2 99.07(5) . 4_556 ? O1 Ca1 O2 167.39(4) 4_456 4_556 ? O1S Ca1 O1 156.02(6) . . ? O3 Ca1 O1 85.93(5) . . ? O4 Ca1 O1 84.78(5) . . ? O1 Ca1 O1 120.72(4) 4_456 . ? O2 Ca1 O1 71.59(4) 4_556 . ? O1S Ca1 O2 151.43(6) . . ? O3 Ca1 O2 83.00(5) . . ? O4 Ca1 O2 90.60(5) . . ? O1 Ca1 O2 71.03(4) 4_456 . ? O2 Ca1 O2 121.56(4) 4_556 . ? O1 Ca1 O2 51.99(4) . . ? O1S Ca1 C1 175.98(7) . . ? O3 Ca1 C1 84.44(5) . . ? O4 Ca1 C1 86.83(5) . . ? O1 Ca1 C1 95.87(5) 4_456 . ? O2 Ca1 C1 96.68(5) 4_556 . ? O1 Ca1 C1 25.89(5) . . ? O2 Ca1 C1 26.12(5) . . ? O1S Ca1 Ca1 121.02(5) . 4_556 ? O3 Ca1 Ca1 65.60(4) . 4_556 ? O4 Ca1 Ca1 106.93(4) . 4_556 ? O1 Ca1 Ca1 152.71(3) 4_456 4_556 ? O2 Ca1 Ca1 39.49(3) 4_556 4_556 ? O1 Ca1 Ca1 37.47(3) . 4_556 ? O2 Ca1 Ca1 82.48(3) . 4_556 ? C1 Ca1 Ca1 59.23(4) . 4_556 ? O1S Ca1 Ca1 120.32(5) . 4_456 ? O3 Ca1 Ca1 108.26(4) . 4_456 ? O4 Ca1 Ca1 69.70(4) . 4_456 ? O1 Ca1 Ca1 38.32(3) 4_456 4_456 ? O2 Ca1 Ca1 153.02(3) 4_556 4_456 ? O1 Ca1 Ca1 82.76(3) . 4_456 ? O2 Ca1 Ca1 38.03(3) . 4_456 ? C1 Ca1 Ca1 59.26(4) . 4_456 ? Ca1 Ca1 Ca1 118.496(14) 4_556 4_456 ? C1 O1 Ca1 136.10(10) . 4_556 ? C1 O1 Ca1 93.87(9) . . ? Ca1 O1 Ca1 104.21(4) 4_556 . ? C1 O2 Ca1 134.42(11) . 4_456 ? C1 O2 Ca1 91.56(9) . . ? Ca1 O2 Ca1 102.48(4) 4_456 . ? C12 O3 Ca1 138.27(12) . . ? C12 O4 Ca1 131.43(12) 4_456 . ? O1 C1 O2 122.51(13) . . ? O1 C1 C2 118.26(15) . . ? O2 C1 C2 119.19(15) . . ? O1 C1 Ca1 60.23(8) . . ? O2 C1 Ca1 62.33(7) . . ? C2 C1 Ca1 175.63(11) . . ? C3 C2 C7 120.04(14) . . ? C3 C2 C1 118.03(14) . . ? C7 C2 C1 121.93(14) . . ? C2 C3 C4 120.45(16) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 121.63(17) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 119.57(14) . . ? C4 C5 C12 117.35(16) . 2_564 ? C6 C5 C12 123.08(15) . 2_564 ? C5 C6 C8 123.12(14) . . ? C5 C6 C7 118.81(14) . . ? C8 C6 C7 118.06(15) . . ? C11 C7 C2 121.89(14) . . ? C11 C7 C6 118.89(15) . . ? C2 C7 C6 119.21(14) . . ? C9 C8 C6 121.11(16) . . ? C9 C8 H8A 119.4 . . ? C6 C8 H8A 119.4 . . ? C8 C9 C10 120.76(19) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C7 121.01(18) . . ? C10 C11 H11A 119.5 . . ? C7 C11 H11A 119.5 . . ? O3 C12 O4 125.76(15) . 4_556 ? O3 C12 C5 117.84(17) . 2_565 ? O4 C12 C5 116.39(16) 4_556 2_565 ? C1S O1S C1S' 38.4(3) . . ? C1S O1S Ca1 178.2(3) . . ? C1S' O1S Ca1 143.4(4) . . ? O1S C1S N1S 122.2(7) . . ? O1S C1S H1S 118.9 . . ? N1S C1S H1S 118.9 . . ? C1S N1S C3S 120.1(6) . . ? C1S N1S C2S 123.4(6) . . ? C3S N1S C2S 116.3(5) . . ? O1S C1S' N1S' 118.6(8) . . ? O1S C1S' H1S' 120.7 . . ? N1S' C1S' H1S' 120.7 . . ? C1S' N1S' C2S' 121.0(12) . . ? C1S' N1S' C3S' 121.6(7) . . ? C2S' N1S' C3S' 117.3(9) . . ? N1S' C2S' H2S4 109.5 . . ? N1S' C2S' H2S5 109.5 . . ? H2S4 C2S' H2S5 109.5 . . ? N1S' C2S' H2S6 109.5 . . ? H2S4 C2S' H2S6 109.5 . . ? H2S5 C2S' H2S6 109.5 . . ? N1S' C3S' H3S4 109.5 . . ? N1S' C3S' H3S5 109.5 . . ? H3S4 C3S' H3S5 109.5 . . ? N1S' C3S' H3S6 109.5 . . ? H3S4 C3S' H3S6 109.5 . . ? H3S5 C3S' H3S6 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.290 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 959384' ####################################################################### # # 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 'C15 H13 N O5 Sr' _chemical_formula_weight 374.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.88830(10) _cell_length_b 14.7074(2) _cell_length_c 14.9810(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1517.71(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 160 _cell_measurement_theta_min 3.5475 _cell_measurement_theta_max 26.1466 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 3.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5944 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 14110 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3751 _reflns_number_gt 3574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0565P)^2^+0.2346P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.467(8) _refine_ls_number_reflns 3751 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.004 _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 Sr1 Sr 0.14462(4) 0.692322(15) 0.453358(15) 0.02068(8) Uani 1 1 d . . . C2 C 0.1342(4) 0.92982(18) 0.64506(18) 0.0245(5) Uani 1 1 d . . . O1 O 0.2809(3) 0.79965(15) 0.58034(13) 0.0290(4) Uani 1 1 d . . . C7 C 0.1209(4) 1.02212(19) 0.62154(19) 0.0280(6) Uani 1 1 d . . . O4 O 0.5049(3) 0.65251(14) 0.47878(13) 0.0274(4) Uani 1 1 d . . . O3 O 0.3163(4) 0.7997(2) 0.3550(2) 0.0590(8) Uani 1 1 d . . . C3 C 0.1381(5) 0.9050(2) 0.7330(2) 0.0378(7) Uani 1 1 d . . . H3A H 0.1555 0.8443 0.7484 0.045 Uiso 1 1 calc R . . C6 C 0.1152(4) 1.0902(2) 0.6885(2) 0.0310(6) Uani 1 1 d . . . C1 C 0.1420(4) 0.85408(17) 0.57664(17) 0.0234(5) Uani 1 1 d . . . C4 C 0.1157(5) 0.9711(2) 0.8008(2) 0.0403(8) Uani 1 1 d . . . H4A H 0.1069 0.9530 0.8602 0.048 Uiso 1 1 calc R . . C5 C 0.1070(4) 1.0613(2) 0.7800(2) 0.0312(7) Uani 1 1 d . . . O1S O 0.1400(5) 0.5737(3) 0.3400(3) 0.0976(15) Uani 1 1 d . . . C14 C -0.0903(5) 0.6271(3) 0.6418(2) 0.0442(9) Uani 1 1 d . . . C13 C 0.1196(6) 1.0511(2) 0.5307(2) 0.0484(10) Uani 1 1 d . . . H13A H 0.1239 1.0077 0.4856 0.058 Uiso 1 1 calc R . . C11 C 0.1093(9) 1.2071(3) 0.5746(3) 0.0702(14) Uani 1 1 d . . . H11A H 0.1057 1.2682 0.5588 0.084 Uiso 1 1 calc R . . C10 C 0.1117(6) 1.1830(2) 0.6626(3) 0.0486(9) Uani 1 1 d . . . H10A H 0.1111 1.2280 0.7062 0.058 Uiso 1 1 calc R . . C12 C 0.1121(9) 1.1408(3) 0.5086(3) 0.0723(16) Uani 1 1 d . . . H12A H 0.1089 1.1578 0.4488 0.087 Uiso 1 1 calc R . . O2 O 0.0138(5) 0.6018(2) 0.5789(2) 0.0608(8) Uani 1 1 d . . . N1S N 0.1169(5) 0.4333(3) 0.2935(4) 0.0880(17) Uani 1 1 d . . . C1S C 0.1324(8) 0.5108(5) 0.2870(6) 0.109(3) Uani 1 1 d . . . H1SA H 0.1410 0.5299 0.2279 0.131 Uiso 1 1 calc R . . C3S C 0.1152(7) 0.3551(4) 0.2406(5) 0.105(3) Uani 1 1 d . . . H3S1 H 0.0847 0.3712 0.1801 0.158 Uiso 1 1 calc R . . H3S2 H 0.0192 0.3135 0.2628 0.158 Uiso 1 1 calc R . . H3S3 H 0.2407 0.3267 0.2425 0.158 Uiso 1 1 calc R . . C2S C 0.1170(10) 0.4172(9) 0.3940(7) 0.176(6) Uani 1 1 d . . . H2S1 H 0.1160 0.4747 0.4245 0.264 Uiso 1 1 calc R . . H2S2 H 0.2313 0.3839 0.4105 0.264 Uiso 1 1 calc R . . H2S3 H 0.0037 0.3831 0.4104 0.264 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 Sr1 0.02085(10) 0.02001(11) 0.02118(11) -0.00189(9) 0.00229(9) -0.00198(9) C2 0.0189(10) 0.0244(12) 0.0302(12) -0.0088(10) 0.0004(11) -0.0023(11) O1 0.0250(8) 0.0309(11) 0.0310(9) -0.0101(9) 0.0008(8) 0.0025(8) C7 0.0270(13) 0.0260(13) 0.0311(14) -0.0072(11) 0.0004(11) -0.0010(11) O4 0.0249(9) 0.0258(10) 0.0314(10) -0.0076(8) 0.0024(7) 0.0027(7) O3 0.0637(18) 0.0478(15) 0.0655(17) 0.0339(13) 0.0230(14) 0.0055(13) C3 0.0520(17) 0.0312(15) 0.0301(14) -0.0077(11) -0.0056(15) 0.0014(15) C6 0.0264(14) 0.0299(15) 0.0367(15) -0.0110(12) -0.0022(11) 0.0015(11) C1 0.0215(11) 0.0252(12) 0.0234(11) -0.0037(9) 0.0043(11) -0.0048(11) C4 0.053(2) 0.0462(19) 0.0213(13) -0.0080(12) -0.0029(13) 0.0028(16) C5 0.0250(14) 0.0334(16) 0.0353(15) -0.0168(12) -0.0022(11) 0.0050(10) O1S 0.0511(16) 0.106(3) 0.135(3) -0.094(3) -0.007(2) 0.006(2) C14 0.0394(17) 0.053(2) 0.0404(17) 0.0270(16) -0.0151(14) -0.0167(15) C13 0.080(3) 0.0265(15) 0.0384(18) -0.0012(12) 0.0100(18) 0.0030(16) C11 0.109(4) 0.030(2) 0.072(3) 0.0065(18) 0.011(3) -0.001(2) C10 0.060(2) 0.0262(16) 0.059(2) -0.0122(15) 0.0013(17) 0.0023(15) C12 0.128(5) 0.047(3) 0.042(2) 0.0105(18) 0.007(3) 0.003(3) O2 0.0651(18) 0.072(2) 0.0448(14) 0.0295(14) 0.0087(14) -0.0173(15) N1S 0.0359(19) 0.072(3) 0.156(5) -0.056(3) 0.005(2) 0.0016(19) C1S 0.043(2) 0.103(5) 0.181(7) -0.090(5) -0.009(4) 0.011(3) C3S 0.048(3) 0.099(4) 0.168(6) -0.095(4) 0.014(3) -0.009(2) C2S 0.061(4) 0.308(16) 0.159(9) -0.117(10) -0.011(5) 0.021(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 Sr1 O1S 2.435(3) . ? Sr1 O3 2.463(2) . ? Sr1 O2 2.474(3) . ? Sr1 O1 2.559(2) 4_466 ? Sr1 O4 2.5781(19) . ? Sr1 O1 2.644(2) . ? Sr1 O4 2.677(2) 4_466 ? Sr1 C1 3.012(2) . ? Sr1 C14 3.393(3) . ? Sr1 Sr1 4.0858(2) 4_466 ? Sr1 Sr1 4.0858(2) 4_566 ? C2 C3 1.367(4) . ? C2 C7 1.405(4) . ? C2 C1 1.515(3) . ? O1 C1 1.249(3) . ? O1 Sr1 2.559(2) 4_566 ? C7 C6 1.418(4) . ? C7 C13 1.426(4) . ? O4 C1 1.261(3) 4_566 ? O4 Sr1 2.677(2) 4_566 ? O3 C14 1.256(5) 4_566 ? C3 C4 1.415(4) . ? C3 H3A 0.9300 . ? C6 C10 1.419(5) . ? C6 C5 1.435(5) . ? C1 O4 1.261(3) 4_466 ? C4 C5 1.364(5) . ? C4 H4A 0.9300 . ? C5 C14 1.523(4) 3_556 ? O1S C1S 1.220(6) . ? C14 O2 1.242(5) . ? C14 O3 1.256(5) 4_466 ? C14 C5 1.523(4) 3_546 ? C13 C12 1.361(5) . ? C13 H13A 0.9300 . ? C11 C10 1.365(6) . ? C11 C12 1.390(7) . ? C11 H11A 0.9300 . ? C10 H10A 0.9300 . ? C12 H12A 0.9300 . ? N1S C1S 1.150(8) . ? N1S C3S 1.397(6) . ? N1S C2S 1.525(12) . ? C1S H1SA 0.9300 . ? C3S H3S1 0.9600 . ? C3S H3S2 0.9600 . ? C3S H3S3 0.9600 . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 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 O1S Sr1 O3 92.76(15) . . ? O1S Sr1 O2 98.03(15) . . ? O3 Sr1 O2 167.15(12) . . ? O1S Sr1 O1 83.26(9) . 4_466 ? O3 Sr1 O1 108.82(8) . 4_466 ? O2 Sr1 O1 79.52(9) . 4_466 ? O1S Sr1 O4 87.30(9) . . ? O3 Sr1 O4 76.81(8) . . ? O2 Sr1 O4 96.66(9) . . ? O1 Sr1 O4 169.19(6) 4_466 . ? O1S Sr1 O1 159.10(9) . . ? O3 Sr1 O1 82.95(9) . . ? O2 Sr1 O1 84.49(10) . . ? O1 Sr1 O1 117.52(5) 4_466 . ? O4 Sr1 O1 71.80(6) . . ? O1S Sr1 O4 150.56(11) . 4_466 ? O3 Sr1 O4 81.57(8) . 4_466 ? O2 Sr1 O4 92.25(9) . 4_466 ? O1 Sr1 O4 71.55(6) 4_466 4_466 ? O4 Sr1 O4 118.92(5) . 4_466 ? O1 Sr1 O4 49.12(6) . 4_466 ? O1S Sr1 C1 173.49(13) . . ? O3 Sr1 C1 82.15(9) . . ? O2 Sr1 C1 87.53(10) . . ? O1 Sr1 C1 94.51(7) 4_466 . ? O4 Sr1 C1 95.43(7) . . ? O1 Sr1 C1 24.41(7) . . ? O4 Sr1 C1 24.73(7) 4_466 . ? O1S Sr1 C14 111.82(14) . . ? O3 Sr1 C14 155.30(10) . . ? O2 Sr1 C14 16.58(11) . . ? O1 Sr1 C14 73.16(7) 4_466 . ? O4 Sr1 C14 105.78(7) . . ? O1 Sr1 C14 74.90(8) . . ? O4 Sr1 C14 75.74(8) 4_466 . ? C1 Sr1 C14 73.16(8) . . ? O1S Sr1 Sr1 121.67(8) . 4_466 ? O3 Sr1 Sr1 110.08(6) . 4_466 ? O2 Sr1 Sr1 69.92(8) . 4_466 ? O1 Sr1 Sr1 39.00(4) 4_466 4_466 ? O4 Sr1 Sr1 148.78(4) . 4_466 ? O1 Sr1 Sr1 78.77(4) . 4_466 ? O4 Sr1 Sr1 38.11(4) 4_466 4_466 ? C1 Sr1 Sr1 57.12(5) . 4_466 ? C14 Sr1 Sr1 55.31(6) . 4_466 ? O1S Sr1 Sr1 123.17(8) . 4_566 ? O3 Sr1 Sr1 62.20(8) . 4_566 ? O2 Sr1 Sr1 105.70(8) . 4_566 ? O1 Sr1 Sr1 150.90(5) 4_466 4_566 ? O4 Sr1 Sr1 39.86(5) . 4_566 ? O1 Sr1 Sr1 37.51(4) . 4_566 ? O4 Sr1 Sr1 79.58(4) 4_466 4_566 ? C1 Sr1 Sr1 57.81(5) . 4_566 ? C14 Sr1 Sr1 103.58(6) . 4_566 ? Sr1 Sr1 Sr1 114.907(10) 4_466 4_566 ? C3 C2 C7 120.0(2) . . ? C3 C2 C1 117.1(2) . . ? C7 C2 C1 122.9(2) . . ? C1 O1 Sr1 135.40(19) . 4_566 ? C1 O1 Sr1 94.52(16) . . ? Sr1 O1 Sr1 103.49(7) 4_566 . ? C2 C7 C6 120.4(3) . . ? C2 C7 C13 121.9(3) . . ? C6 C7 C13 117.7(3) . . ? C1 O4 Sr1 129.87(17) 4_566 . ? C1 O4 Sr1 92.65(15) 4_566 4_566 ? Sr1 O4 Sr1 102.04(7) . 4_566 ? C14 O3 Sr1 140.6(3) 4_566 . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C7 C6 C10 119.1(3) . . ? C7 C6 C5 117.9(3) . . ? C10 C6 C5 123.0(3) . . ? O1 C1 O4 123.6(2) . 4_466 ? O1 C1 C2 118.0(2) . . ? O4 C1 C2 118.4(2) 4_466 . ? O1 C1 Sr1 61.07(14) . . ? O4 C1 Sr1 62.62(13) 4_466 . ? C2 C1 Sr1 174.92(18) . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 C14 116.4(3) . 3_556 ? C6 C5 C14 123.3(3) . 3_556 ? C1S O1S Sr1 176.0(6) . . ? O2 C14 O3 125.6(3) . 4_466 ? O2 C14 C5 116.0(3) . 3_546 ? O3 C14 C5 118.5(3) 4_466 3_546 ? O2 C14 Sr1 34.64(18) . . ? O3 C14 Sr1 91.9(2) 4_466 . ? C5 C14 Sr1 148.8(2) 3_546 . ? C12 C13 C7 121.5(3) . . ? C12 C13 H13A 119.3 . . ? C7 C13 H13A 119.3 . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C10 C6 120.9(3) . . ? C11 C10 H10A 119.5 . . ? C6 C10 H10A 119.5 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C14 O2 Sr1 128.8(3) . . ? C1S N1S C3S 140.3(8) . . ? C1S N1S C2S 103.7(7) . . ? C3S N1S C2S 115.7(7) . . ? N1S C1S O1S 134.5(9) . . ? N1S C1S H1SA 112.8 . . ? O1S C1S H1SA 112.8 . . ? N1S C3S H3S1 109.5 . . ? N1S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? N1S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? N1S C2S H2S1 109.5 . . ? N1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? N1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.813 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 959224' ####################################################################### # # 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 'C15 H13 Ba N O5' _chemical_formula_sum 'C15 H13 Ba N O5' _chemical_formula_weight 424.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.1269(3) _cell_length_b 14.6724(6) _cell_length_c 15.0027(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1568.81(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9378 _cell_measurement_theta_min 2.7153 _cell_measurement_theta_max 28.2945 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 2.553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5147 _exptl_absorpt_correction_T_max 0.7007 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 13779 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3909 _reflns_number_gt 3623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0149P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(19) _refine_ls_number_reflns 3909 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0512 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.007 _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 Ba1 Ba 0.07272(3) 0.805881(13) 0.560967(12) 0.02467(6) Uani 1 1 d . . . O1 O 0.2073(4) 0.73816(16) 0.39771(15) 0.0303(6) Uani 1 1 d . . . O2 O 0.4463(4) 0.83161(15) 0.55639(16) 0.0339(5) Uani 1 1 d . . . O3 O 0.1847(6) 0.6755(2) 0.6701(3) 0.0742(11) Uani 1 1 d . . . O4 O 0.3449(5) 0.6162(2) 0.5575(2) 0.0631(9) Uani 1 1 d . . . C1 C 0.0840(6) 0.6772(2) 0.39102(19) 0.0262(7) Uani 1 1 d . . . C2 C 0.1056(5) 0.6066(2) 0.3190(2) 0.0283(8) Uani 1 1 d . . . C3 C 0.1407(5) 0.6297(3) 0.2289(2) 0.0309(8) Uani 1 1 d . . . C4 C 0.1668(6) 0.5589(3) 0.1648(2) 0.0337(9) Uani 1 1 d . . . C5 C 0.1715(6) 0.4659(3) 0.1953(3) 0.0371(9) Uani 1 1 d . . . C6 C 0.1390(6) 0.4479(3) 0.2824(3) 0.0389(10) Uani 1 1 d . . . H6A H 0.1429 0.3878 0.3019 0.047 Uiso 1 1 calc R . . C7 C 0.0995(6) 0.5171(2) 0.3443(2) 0.0350(9) Uani 1 1 d . . . H7A H 0.0692 0.5019 0.4028 0.042 Uiso 1 1 calc R . . C8 C 0.1442(6) 0.7213(3) 0.1987(3) 0.0457(11) Uani 1 1 d . . . H8A H 0.1297 0.7683 0.2397 0.055 Uiso 1 1 calc R . . C9 C 0.1682(8) 0.7415(3) 0.1113(3) 0.0656(16) Uani 1 1 d . . . H9A H 0.1703 0.8021 0.0931 0.079 Uiso 1 1 calc R . . C10 C 0.1899(8) 0.6720(3) 0.0479(3) 0.0655(15) Uani 1 1 d . . . H10A H 0.2039 0.6867 -0.0121 0.079 Uiso 1 1 calc R . . C11 C 0.1906(7) 0.5832(3) 0.0737(3) 0.0523(11) Uani 1 1 d . . . H11A H 0.2068 0.5377 0.0312 0.063 Uiso 1 1 calc R . . C12 C 0.2812(7) 0.6147(3) 0.6361(3) 0.0501(12) Uani 1 1 d . . . O1S O 0.0938(6) 0.9446(3) 0.6720(3) 0.0920(13) Uani 1 1 d . . . C1S C 0.1216(7) 0.9921(4) 0.7383(4) 0.0729(17) Uani 1 1 d . . . H1SA H 0.1154 1.0550 0.7309 0.087 Uiso 1 1 calc R . . N1S N 0.1597(6) 0.9612(3) 0.8194(4) 0.0715(14) Uani 1 1 d . . . C2S C 0.1632(9) 0.8662(4) 0.8332(5) 0.100(2) Uani 1 1 d . . . H2S1 H 0.1304 0.8356 0.7789 0.150 Uiso 1 1 calc R . . H2S2 H 0.0747 0.8503 0.8789 0.150 Uiso 1 1 calc R . . H2S3 H 0.2868 0.8480 0.8513 0.150 Uiso 1 1 calc R . . C3S C 0.1850(9) 1.0241(4) 0.8916(4) 0.103(2) Uani 1 1 d . . . H3S1 H 0.1846 1.0853 0.8688 0.154 Uiso 1 1 calc R . . H3S2 H 0.3027 1.0122 0.9204 0.154 Uiso 1 1 calc R . . H3S3 H 0.0847 1.0170 0.9337 0.154 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 Ba1 0.02286(9) 0.02618(9) 0.02495(8) -0.00231(9) -0.00198(10) 0.00126(10) O1 0.0231(14) 0.0360(14) 0.0318(13) -0.0064(11) -0.0023(12) -0.0030(12) O2 0.0290(14) 0.0388(13) 0.0339(12) -0.0121(10) -0.0072(15) 0.0043(11) O3 0.081(3) 0.055(2) 0.086(3) 0.0347(19) 0.002(2) 0.026(2) O4 0.069(2) 0.074(2) 0.0463(17) 0.0321(18) -0.0086(18) -0.0283(17) C1 0.0222(17) 0.0330(19) 0.0235(14) -0.0040(12) -0.0057(16) 0.0052(17) C2 0.023(2) 0.0327(18) 0.0288(16) -0.0060(14) -0.0031(15) 0.0058(15) C3 0.025(2) 0.037(2) 0.0304(18) -0.0031(16) 0.0016(16) -0.0003(16) C4 0.023(2) 0.048(2) 0.0306(19) -0.0081(17) 0.0010(16) 0.0010(17) C5 0.027(2) 0.043(2) 0.041(2) -0.0195(18) 0.0003(18) -0.0037(18) C6 0.046(3) 0.028(2) 0.043(2) -0.0043(16) 0.0017(18) -0.0002(17) C7 0.042(3) 0.036(2) 0.0269(17) -0.0032(14) 0.0082(18) -0.0030(19) C8 0.056(3) 0.040(2) 0.040(2) 0.0024(18) 0.001(2) 0.0106(19) C9 0.093(4) 0.058(3) 0.047(3) 0.017(2) 0.009(3) 0.001(3) C10 0.087(4) 0.081(4) 0.029(2) 0.006(2) 0.010(2) -0.001(3) C11 0.056(3) 0.070(3) 0.031(2) -0.010(2) 0.010(2) -0.001(3) C12 0.040(3) 0.051(3) 0.059(3) 0.032(2) -0.011(2) -0.014(2) O1S 0.075(3) 0.093(3) 0.108(3) -0.069(2) 0.008(3) -0.002(3) C1S 0.047(4) 0.077(4) 0.095(4) -0.043(3) 0.008(3) -0.003(3) N1S 0.046(3) 0.070(3) 0.098(4) -0.037(3) 0.015(3) -0.005(2) C2S 0.064(4) 0.079(4) 0.158(7) -0.021(4) 0.005(5) -0.001(4) C3S 0.065(4) 0.127(5) 0.116(5) -0.085(4) 0.000(4) 0.000(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 Ba1 O1S 2.634(3) . ? Ba1 O3 2.642(3) . ? Ba1 O4 2.665(3) 4_466 ? Ba1 O2 2.690(3) . ? Ba1 O1 2.754(3) 4_466 ? Ba1 O1 2.812(2) . ? Ba1 O2 2.825(2) 4_466 ? Ba1 C1 3.174(3) . ? Ba1 C12 3.368(4) . ? Ba1 Ba1 4.3282(2) 4_466 ? Ba1 Ba1 4.3282(2) 4_566 ? O1 C1 1.258(4) . ? O1 Ba1 2.754(3) 4_566 ? O2 C1 1.266(4) 4_566 ? O2 Ba1 2.825(2) 4_566 ? O3 C12 1.236(6) . ? O4 C12 1.264(5) . ? O4 Ba1 2.665(3) 4_566 ? C1 O2 1.266(4) 4_466 ? C1 C2 1.505(4) . ? C2 C7 1.368(5) . ? C2 C3 1.416(5) . ? C3 C8 1.418(5) . ? C3 C4 1.429(5) . ? C4 C11 1.422(5) . ? C4 C5 1.439(5) . ? C5 C6 1.353(6) . ? C5 C12 1.517(5) 2_564 ? C6 C7 1.404(5) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.356(5) . ? C8 H8A 0.9300 . ? C9 C10 1.403(6) . ? C9 H9A 0.9300 . ? C10 C11 1.359(6) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C5 1.517(5) 2_565 ? O1S C1S 1.231(6) . ? C1S N1S 1.326(7) . ? C1S H1SA 0.9300 . ? N1S C2S 1.409(7) . ? N1S C3S 1.435(6) . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C3S H3S1 0.9600 . ? C3S H3S2 0.9600 . ? C3S H3S3 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 O1S Ba1 O3 98.63(13) . . ? O1S Ba1 O4 97.19(12) . 4_466 ? O3 Ba1 O4 155.25(11) . 4_466 ? O1S Ba1 O2 81.45(11) . . ? O3 Ba1 O2 79.55(10) . . ? O4 Ba1 O2 121.72(9) 4_466 . ? O1S Ba1 O1 95.32(11) . 4_466 ? O3 Ba1 O1 88.63(10) . 4_466 ? O4 Ba1 O1 71.02(8) 4_466 4_466 ? O2 Ba1 O1 167.07(7) . 4_466 ? O1S Ba1 O1 143.56(11) . . ? O3 Ba1 O1 100.44(10) . . ? O4 Ba1 O1 77.21(9) 4_466 . ? O2 Ba1 O1 71.92(7) . . ? O1 Ba1 O1 115.83(6) 4_466 . ? O1S Ba1 O2 164.57(11) . 4_466 ? O3 Ba1 O2 88.03(11) . 4_466 ? O4 Ba1 O2 72.33(9) 4_466 4_466 ? O2 Ba1 O2 113.58(6) . 4_466 ? O1 Ba1 O2 70.80(7) 4_466 4_466 ? O1 Ba1 O2 46.65(7) . 4_466 ? O1S Ba1 C1 165.07(12) . . ? O3 Ba1 C1 93.41(10) . . ? O4 Ba1 C1 74.63(10) 4_466 . ? O2 Ba1 C1 92.17(9) . . ? O1 Ba1 C1 93.74(9) 4_466 . ? O1 Ba1 C1 23.26(8) . . ? O2 Ba1 C1 23.45(9) 4_466 . ? O1S Ba1 C12 113.97(13) . . ? O3 Ba1 C12 19.31(11) . . ? O4 Ba1 C12 148.13(11) 4_466 . ? O2 Ba1 C12 71.87(9) . . ? O1 Ba1 C12 98.42(9) 4_466 . ? O1 Ba1 C12 81.19(10) . . ? O2 Ba1 C12 75.80(10) 4_466 . ? C1 Ba1 C12 76.25(10) . . ? O1S Ba1 Ba1 127.37(10) . 4_466 ? O3 Ba1 Ba1 103.67(9) . 4_466 ? O4 Ba1 Ba1 51.62(7) 4_466 4_466 ? O2 Ba1 Ba1 149.01(5) . 4_466 ? O1 Ba1 Ba1 39.44(5) 4_466 4_466 ? O1 Ba1 Ba1 77.22(5) . 4_466 ? O2 Ba1 Ba1 37.20(6) 4_466 4_466 ? C1 Ba1 Ba1 57.04(8) . 4_466 ? C12 Ba1 Ba1 100.91(8) . 4_466 ? O1S Ba1 Ba1 120.86(10) . 4_566 ? O3 Ba1 Ba1 74.87(9) . 4_566 ? O4 Ba1 Ba1 112.48(7) 4_466 4_566 ? O2 Ba1 Ba1 39.42(5) . 4_566 ? O1 Ba1 Ba1 141.70(5) 4_466 4_566 ? O1 Ba1 Ba1 38.47(5) . 4_566 ? O2 Ba1 Ba1 74.26(5) 4_466 4_566 ? C1 Ba1 Ba1 54.14(8) . 4_566 ? C12 Ba1 Ba1 57.50(9) . 4_566 ? Ba1 Ba1 Ba1 110.834(8) 4_466 4_566 ? C1 O1 Ba1 120.8(2) . 4_566 ? C1 O1 Ba1 94.74(19) . . ? Ba1 O1 Ba1 102.09(7) 4_566 . ? C1 O2 Ba1 137.5(2) 4_566 . ? C1 O2 Ba1 93.91(18) 4_566 4_566 ? Ba1 O2 Ba1 103.38(8) . 4_566 ? C12 O3 Ba1 115.7(3) . . ? C12 O4 Ba1 148.0(3) . 4_566 ? O1 C1 O2 124.4(3) . 4_466 ? O1 C1 C2 118.4(3) . . ? O2 C1 C2 117.2(3) 4_466 . ? O1 C1 Ba1 62.00(16) . . ? O2 C1 Ba1 62.63(15) 4_466 . ? C2 C1 Ba1 171.5(2) . . ? C7 C2 C3 120.0(3) . . ? C7 C2 C1 117.3(3) . . ? C3 C2 C1 122.6(3) . . ? C2 C3 C8 122.3(3) . . ? C2 C3 C4 119.5(3) . . ? C8 C3 C4 118.2(3) . . ? C11 C4 C3 118.7(4) . . ? C11 C4 C5 122.7(4) . . ? C3 C4 C5 118.5(3) . . ? C6 C5 C4 119.2(3) . . ? C6 C5 C12 116.8(4) . 2_564 ? C4 C5 C12 123.9(4) . 2_564 ? C5 C6 C7 122.2(4) . . ? C5 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C2 C7 C6 120.2(3) . . ? C2 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C9 C8 C3 121.2(4) . . ? C9 C8 H8A 119.4 . . ? C3 C8 H8A 119.4 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C4 120.9(4) . . ? C10 C11 H11A 119.5 . . ? C4 C11 H11A 119.5 . . ? O3 C12 O4 125.0(4) . . ? O3 C12 C5 116.3(4) . 2_565 ? O4 C12 C5 118.7(5) . 2_565 ? O3 C12 Ba1 45.0(2) . . ? O4 C12 Ba1 80.3(2) . . ? C5 C12 Ba1 160.6(3) 2_565 . ? C1S O1S Ba1 163.4(4) . . ? O1S C1S N1S 125.4(6) . . ? O1S C1S H1SA 117.3 . . ? N1S C1S H1SA 117.3 . . ? C1S N1S C2S 118.5(5) . . ? C1S N1S C3S 119.8(5) . . ? C2S N1S C3S 121.5(6) . . ? N1S C2S H2S1 109.5 . . ? N1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? N1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? N1S C3S H3S1 109.5 . . ? N1S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? N1S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.639 _refine_diff_density_min -0.671 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 959225'