Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 _publ_contact_author_name 'Christopher L. Cahill' _publ_contact_author_address ; Department of Chemistry George Washington University 725 21st Street, NW Washington, DC 20052 ; _publ_contact_author_email cahill@gwu.edu _publ_contact_author_phone 202-994-6959 _publ_contact_author_fax 202-994-5873 _publ_section_title ; Templated Metal-Organic Frameworks: Synthesis, Structures, Thermal Properties and Solid-State Transformation of Two Novel Calcium-Adipate Frameworks ; _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name _publ_author_address 'de Lill, Daniel T.' ; Department of Chemistry The George Washington University 725 21st Street, NW Washington, DC 20052 ; 'Bozzuto, Daniel J.' ; Department of Chemistry The George Washington University 725 21st Street, NW Washington, DC 20052 ; 'Cahill, Christopher L.' ; Department of Chemistry The George Washington University 725 21st Street, NW Washington, DC 20052 AND Carnegie Insitution of Washington Geophysical Laboratory 5251 Broad Branch Road, NW Washington, DC 20015 ; data_dd2_34 _database_code_depnum_ccdc_archive 'CCDC 264131' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Ca1 N2 O6' _chemical_formula_weight 376.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.855(2) _cell_length_b 15.339(3) _cell_length_c 7.7790(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.631(6) _cell_angle_gamma 90.00 _cell_volume 1752.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14660 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.1062 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 29.65 _reflns_number_total 4447 _reflns_number_gt 2375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.05 (Bruker-AXS)' _computing_cell_refinement 'SAINT (Bruker-AXS)' _computing_data_reduction 'SAINT (Bruker-AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4447 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _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 Ca1 Ca 0.77947(3) 0.28071(3) 0.45111(6) 0.02757(13) Uani 1 1 d . . . O1 O 0.84998(11) 0.18470(11) 0.2336(2) 0.0348(4) Uani 1 1 d . . . O2 O 0.88093(11) 0.15228(11) 0.5107(2) 0.0395(5) Uani 1 1 d . . . O3 O 0.66960(11) 0.15820(11) 0.3909(2) 0.0380(5) Uani 1 1 d . . . O4 O 0.70441(11) 0.32138(11) 0.1726(2) 0.0368(5) Uani 1 1 d . . . O6 O 0.67096(17) 0.38282(14) 0.5447(3) 0.0449(6) Uani 1 1 d . . . O5 O 0.88928(16) 0.38214(14) 0.3624(3) 0.0422(5) Uani 1 1 d . . . N1 N 0.48525(17) 0.36419(18) 0.3745(3) 0.0538(7) Uani 1 1 d . . . N2 N 0.07646(18) 0.1459(2) 0.0133(3) 0.0611(7) Uani 1 1 d . . . C1 C 0.87979(16) 0.13187(17) 0.3534(3) 0.0291(6) Uani 1 1 d . . . C2 C 0.91208(18) 0.04460(17) 0.3043(3) 0.0429(7) Uani 1 1 d . . . H2A H 0.9571 0.0533 0.2275 0.052 Uiso 1 1 calc R . . H2B H 0.8610 0.0141 0.2383 0.052 Uiso 1 1 calc R . . C3 C 0.95381(16) -0.01448(17) 0.4540(3) 0.0421(7) Uani 1 1 d . . . H3A H 0.9122 -0.0175 0.5387 0.050 Uiso 1 1 calc R . . H3B H 0.9596 -0.0728 0.4089 0.050 Uiso 1 1 calc R . . C4 C 0.66844(16) 0.13372(17) 0.5459(3) 0.0290(6) Uani 1 1 d . . . C5 C 0.62179(17) 0.04870(16) 0.5759(3) 0.0371(6) Uani 1 1 d . . . H5C H 0.6211 0.0417 0.6996 0.045 Uiso 1 1 calc R . . H5D H 0.6571 0.0011 0.5383 0.045 Uiso 1 1 calc R . . C6 C 0.52368(16) 0.04220(16) 0.4804(3) 0.0370(7) Uani 1 1 d . . . H6C H 0.4889 0.0913 0.5136 0.044 Uiso 1 1 calc R . . H6D H 0.5245 0.0460 0.3562 0.044 Uiso 1 1 calc R . . C7 C 0.4852(2) 0.2830(2) 0.3128(4) 0.0553(8) Uani 1 1 d . . . H7 H 0.5408 0.2546 0.3190 0.066 Uiso 1 1 calc R . . C8 C 0.40769(19) 0.2384(2) 0.2400(3) 0.0490(8) Uani 1 1 d . . . H8 H 0.4121 0.1814 0.2015 0.059 Uiso 1 1 calc R . . C9 C 0.32357(19) 0.2789(2) 0.2249(3) 0.0447(7) Uani 1 1 d . . . C10 C 0.3235(2) 0.3642(2) 0.2861(4) 0.0511(8) Uani 1 1 d . . . H10A H 0.2691 0.3950 0.2781 0.061 Uiso 1 1 calc R . . C11 C 0.4039(2) 0.4027(2) 0.3586(4) 0.0560(9) Uani 1 1 d . . . H11 H 0.4014 0.4596 0.3992 0.067 Uiso 1 1 calc R . . C14 C 0.23903(19) 0.2331(2) 0.1510(3) 0.0444(7) Uani 1 1 d . . . C13 C 0.2286(2) 0.1439(2) 0.1690(4) 0.0509(8) Uani 1 1 d . . . H13 H 0.2760 0.1109 0.2278 0.061 Uiso 1 1 calc R . . C12 C 0.1475(2) 0.1039(2) 0.0992(4) 0.0578(9) Uani 1 1 d . . . H12 H 0.1426 0.0440 0.1136 0.069 Uiso 1 1 calc R . . C16 C 0.0869(2) 0.2310(3) -0.0050(4) 0.0700(10) Uani 1 1 d . . . H16 H 0.0386 0.2622 -0.0654 0.084 Uiso 1 1 calc R . . C15 C 0.1656(2) 0.2766(2) 0.0602(4) 0.0565(8) Uani 1 1 d . . . H15 H 0.1687 0.3364 0.0427 0.068 Uiso 1 1 calc R . . H6A H 0.610(2) 0.381(2) 0.496(4) 0.091(14) Uiso 1 1 d . . . H6B H 0.669(2) 0.378(2) 0.635(4) 0.067(13) Uiso 1 1 d . . . H5A H 0.8918(19) 0.376(2) 0.270(3) 0.063(12) Uiso 1 1 d . . . H5B H 1.053(2) 0.614(2) 0.585(4) 0.081(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ca1 0.0319(3) 0.0294(3) 0.0212(2) -0.0004(2) 0.00330(19) 0.0007(3) O1 0.0404(11) 0.0371(11) 0.0261(10) 0.0044(8) 0.0026(8) 0.0085(8) O2 0.0482(12) 0.0467(13) 0.0235(10) 0.0006(8) 0.0045(8) 0.0163(9) O3 0.0463(12) 0.0438(12) 0.0238(10) 0.0012(8) 0.0050(8) -0.0100(9) O4 0.0390(11) 0.0451(12) 0.0257(10) 0.0082(8) 0.0022(8) 0.0090(9) O6 0.0510(16) 0.0530(14) 0.0320(13) 0.0006(11) 0.0101(11) 0.0117(11) O5 0.0467(15) 0.0518(14) 0.0283(13) -0.0036(10) 0.0068(11) -0.0112(10) N1 0.0538(19) 0.0603(19) 0.0480(16) 0.0048(14) 0.0096(13) 0.0014(14) N2 0.0480(18) 0.068(2) 0.0676(19) 0.0050(15) 0.0089(14) 0.0021(15) C1 0.0249(14) 0.0313(16) 0.0310(15) 0.0009(12) 0.0038(11) 0.0023(11) C2 0.058(2) 0.0352(18) 0.0343(16) -0.0031(13) 0.0013(13) 0.0078(14) C3 0.0481(19) 0.0323(17) 0.0460(18) 0.0016(13) 0.0078(14) 0.0066(14) C4 0.0237(14) 0.0343(16) 0.0292(15) 0.0000(12) 0.0049(11) 0.0011(11) C5 0.0429(17) 0.0354(17) 0.0323(15) 0.0010(12) 0.0032(12) -0.0059(13) C6 0.0413(17) 0.0354(17) 0.0345(15) -0.0009(12) 0.0066(13) -0.0089(13) C7 0.044(2) 0.072(3) 0.051(2) 0.0094(18) 0.0079(15) 0.0151(18) C8 0.046(2) 0.054(2) 0.0468(18) -0.0001(15) 0.0059(15) 0.0119(15) C9 0.0429(18) 0.055(2) 0.0384(16) 0.0100(15) 0.0124(13) 0.0070(16) C10 0.045(2) 0.055(2) 0.056(2) 0.0068(16) 0.0153(16) 0.0127(16) C11 0.065(3) 0.053(2) 0.053(2) 0.0052(16) 0.0177(18) 0.0054(18) C14 0.0403(18) 0.053(2) 0.0416(17) 0.0063(14) 0.0123(14) 0.0096(15) C13 0.047(2) 0.057(2) 0.0479(19) 0.0073(15) 0.0030(15) 0.0094(16) C12 0.062(3) 0.059(2) 0.053(2) 0.0035(17) 0.0119(18) 0.0028(19) C16 0.044(2) 0.081(3) 0.083(3) 0.014(2) 0.0014(18) 0.016(2) C15 0.046(2) 0.056(2) 0.068(2) 0.0123(18) 0.0110(16) 0.0077(18) _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 O1 2.3485(17) 4_566 ? Ca1 O4 2.3669(17) . ? Ca1 O5 2.428(2) . ? Ca1 O6 2.436(2) . ? Ca1 O2 2.4815(17) . ? Ca1 O3 2.4869(17) . ? Ca1 O1 2.5810(16) . ? Ca1 O4 2.6907(17) 4_566 ? Ca1 C1 2.890(2) . ? Ca1 C4 2.952(3) . ? Ca1 Ca1 4.0020(6) 4_565 ? Ca1 Ca1 4.0020(6) 4_566 ? Ca1 H6B 2.77(3) . ? Ca1 H5A 2.76(3) . ? O1 C1 1.264(3) . ? O1 Ca1 2.3485(17) 4_565 ? O2 C1 1.261(3) . ? O3 C4 1.265(2) . ? O4 C4 1.254(3) 4_565 ? O4 Ca1 2.6907(16) 4_565 ? O6 H6A 0.92(3) . ? O6 H6B 0.71(3) . ? O5 H5A 0.73(3) . ? N1 C7 1.334(4) . ? N1 C11 1.334(3) . ? N2 C16 1.325(4) . ? N2 C12 1.328(4) . ? C1 C2 1.491(3) . ? C2 C3 1.532(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C3 1.516(5) 3_756 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O4 1.254(3) 4_566 ? C4 C5 1.511(3) . ? C5 C6 1.537(3) . ? C5 H5C 0.9700 . ? C5 H5D 0.9700 . ? C6 C6 1.526(4) 3_656 ? C6 H6C 0.9700 . ? C6 H6D 0.9700 . ? C7 C8 1.385(4) . ? C7 H7 0.9300 . ? C8 C9 1.385(3) . ? C8 H8 0.9300 . ? C9 C10 1.392(4) . ? C9 C14 1.478(4) . ? C10 C11 1.376(4) . ? C10 H10A 0.9300 . ? C11 H11 0.9300 . ? C14 C15 1.379(4) . ? C14 C13 1.386(4) . ? C13 C12 1.389(4) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C16 C15 1.391(4) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ca1 O4 151.60(6) 4_566 . ? O1 Ca1 O5 84.08(7) 4_566 . ? O4 Ca1 O5 79.35(7) . . ? O1 Ca1 O6 78.31(8) 4_566 . ? O4 Ca1 O6 82.08(7) . . ? O5 Ca1 O6 100.13(7) . . ? O1 Ca1 O2 80.29(6) 4_566 . ? O4 Ca1 O2 124.74(6) . . ? O5 Ca1 O2 98.44(7) . . ? O6 Ca1 O2 149.90(7) . . ? O1 Ca1 O3 122.32(6) 4_566 . ? O4 Ca1 O3 79.70(6) . . ? O5 Ca1 O3 151.71(7) . . ? O6 Ca1 O3 95.57(7) . . ? O2 Ca1 O3 78.37(6) . . ? O1 Ca1 O1 125.06(7) 4_566 . ? O4 Ca1 O1 74.45(5) . . ? O5 Ca1 O1 79.82(6) . . ? O6 Ca1 O1 156.16(8) . . ? O2 Ca1 O1 51.30(5) . . ? O3 Ca1 O1 76.40(5) . . ? O1 Ca1 O4 72.66(5) 4_566 4_566 ? O4 Ca1 O4 123.78(7) . 4_566 ? O5 Ca1 O4 156.28(7) . 4_566 ? O6 Ca1 O4 80.01(7) . 4_566 ? O2 Ca1 O4 73.54(5) . 4_566 ? O3 Ca1 O4 50.02(5) . 4_566 ? O1 Ca1 O4 109.61(5) . 4_566 ? O1 Ca1 C1 104.43(6) 4_566 . ? O4 Ca1 C1 99.10(7) . . ? O5 Ca1 C1 92.09(7) . . ? O6 Ca1 C1 167.71(7) . . ? O2 Ca1 C1 25.74(5) . . ? O3 Ca1 C1 72.74(6) . . ? O1 Ca1 C1 25.94(5) . . ? O4 Ca1 C1 89.32(6) 4_566 . ? O1 Ca1 C4 97.25(6) 4_566 . ? O4 Ca1 C4 103.06(6) . . ? O5 Ca1 C4 170.01(7) . . ? O6 Ca1 C4 89.82(7) . . ? O2 Ca1 C4 72.14(6) . . ? O3 Ca1 C4 25.08(5) . . ? O1 Ca1 C4 91.42(6) . . ? O4 Ca1 C4 25.14(5) 4_566 . ? C1 Ca1 C4 77.98(6) . . ? O1 Ca1 Ca1 153.82(4) 4_566 4_565 ? O4 Ca1 Ca1 40.63(4) . 4_565 ? O5 Ca1 Ca1 77.09(5) . 4_565 ? O6 Ca1 Ca1 122.57(6) . 4_565 ? O2 Ca1 Ca1 84.62(4) . 4_565 ? O3 Ca1 Ca1 74.63(4) . 4_565 ? O1 Ca1 Ca1 33.82(4) . 4_565 ? O4 Ca1 Ca1 123.07(4) 4_566 4_565 ? C1 Ca1 Ca1 58.88(5) . 4_565 ? C4 Ca1 Ca1 98.30(5) . 4_565 ? O1 Ca1 Ca1 37.71(4) 4_566 4_566 ? O4 Ca1 Ca1 152.01(4) . 4_566 ? O5 Ca1 Ca1 121.67(6) . 4_566 ? O6 Ca1 Ca1 76.37(6) . 4_566 ? O2 Ca1 Ca1 73.74(4) . 4_566 ? O3 Ca1 Ca1 84.80(4) . 4_566 ? O1 Ca1 Ca1 124.20(4) . 4_566 ? O4 Ca1 Ca1 34.94(4) 4_566 4_566 ? C1 Ca1 Ca1 98.32(5) . 4_566 ? C4 Ca1 Ca1 59.73(5) . 4_566 ? Ca1 Ca1 Ca1 152.76(3) 4_565 4_566 ? O1 Ca1 H6B 67.1(6) 4_566 . ? O4 Ca1 H6B 95.5(6) . . ? O5 Ca1 H6B 106.0(7) . . ? O6 Ca1 H6B 13.8(6) . . ? O2 Ca1 H6B 136.2(6) . . ? O3 Ca1 H6B 94.7(7) . . ? O1 Ca1 H6B 167.5(7) . . ? O4 Ca1 H6B 69.5(6) 4_566 . ? C1 Ca1 H6B 158.6(6) . . ? C4 Ca1 H6B 83.5(7) . . ? Ca1 Ca1 H6B 135.6(6) 4_565 . ? Ca1 Ca1 H6B 62.6(6) 4_566 . ? O1 Ca1 H5A 98.0(6) 4_566 . ? O4 Ca1 H5A 68.4(6) . . ? O5 Ca1 H5A 14.5(6) . . ? O6 Ca1 H5A 106.9(6) . . ? O2 Ca1 H5A 96.8(6) . . ? O3 Ca1 H5A 137.3(6) . . ? O1 Ca1 H5A 68.4(6) . . ? O4 Ca1 H5A 167.3(6) 4_566 . ? C1 Ca1 H5A 84.7(6) . . ? C4 Ca1 H5A 159.3(6) . . ? Ca1 Ca1 H5A 62.6(6) 4_565 . ? Ca1 Ca1 H5A 135.1(6) 4_566 . ? H6B Ca1 H5A 115.4(9) . . ? C1 O1 Ca1 153.19(17) . 4_565 ? C1 O1 Ca1 90.80(14) . . ? Ca1 O1 Ca1 108.46(6) 4_565 . ? C1 O2 Ca1 95.53(14) . . ? C4 O3 Ca1 98.47(15) . . ? C4 O4 Ca1 161.93(17) 4_565 . ? C4 O4 Ca1 89.15(14) 4_565 4_565 ? Ca1 O4 Ca1 104.43(6) . 4_565 ? Ca1 O6 H6A 120(2) . . ? Ca1 O6 H6B 111(3) . . ? H6A O6 H6B 103(3) . . ? Ca1 O5 H5A 109(2) . . ? C7 N1 C11 115.4(3) . . ? C16 N2 C12 115.8(3) . . ? O2 C1 O1 120.6(2) . . ? O2 C1 C2 120.9(2) . . ? O1 C1 C2 118.5(2) . . ? O2 C1 Ca1 58.73(12) . . ? O1 C1 Ca1 63.26(13) . . ? C2 C1 Ca1 167.21(18) . . ? C1 C2 C3 116.4(2) . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C3 C2 H2B 108.2 . . ? H2A C2 H2B 107.3 . . ? C3 C3 C2 114.8(3) 3_756 . ? C3 C3 H3A 108.6 3_756 . ? C2 C3 H3A 108.6 . . ? C3 C3 H3B 108.6 3_756 . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.5 . . ? O4 C4 O3 121.4(2) 4_566 . ? O4 C4 C5 120.2(2) 4_566 . ? O3 C4 C5 118.4(2) . . ? O4 C4 Ca1 65.72(13) 4_566 . ? O3 C4 Ca1 56.45(12) . . ? C5 C4 Ca1 169.77(16) . . ? C4 C5 C6 113.9(2) . . ? C4 C5 H5C 108.8 . . ? C6 C5 H5C 108.8 . . ? C4 C5 H5D 108.8 . . ? C6 C5 H5D 108.8 . . ? H5C C5 H5D 107.7 . . ? C6 C6 C5 113.0(3) 3_656 . ? C6 C6 H6C 109.0 3_656 . ? C5 C6 H6C 109.0 . . ? C6 C6 H6D 109.0 3_656 . ? C5 C6 H6D 109.0 . . ? H6C C6 H6D 107.8 . . ? N1 C7 C8 124.3(3) . . ? N1 C7 H7 117.8 . . ? C8 C7 H7 117.8 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 116.1(3) . . ? C8 C9 C14 121.5(3) . . ? C10 C9 C14 122.4(2) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? N1 C11 C10 124.5(3) . . ? N1 C11 H11 117.8 . . ? C10 C11 H11 117.8 . . ? C15 C14 C13 115.9(3) . . ? C15 C14 C9 122.0(3) . . ? C13 C14 C9 122.1(3) . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? N2 C12 C13 124.0(3) . . ? N2 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? N2 C16 C15 124.2(3) . . ? N2 C16 H16 117.9 . . ? C15 C16 H16 117.9 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? 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 O6 H6A N1 0.92(3) 1.97(3) 2.889(4) 173(3) . O6 H6B O3 0.71(3) 2.07(3) 2.769(3) 170(4) 4_566 O5 H5A O2 0.73(3) 2.05(3) 2.771(3) 171(3) 4_565 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 29.65 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.309 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.053 #===END data_gwu01 _database_code_depnum_ccdc_archive 'CCDC 264132' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 Ca N2 O6' _chemical_formula_weight 404.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.3641 1.2855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.8008(8) _cell_length_b 15.0736(7) _cell_length_c 7.7536(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.799(3) _cell_angle_gamma 90.00 _cell_volume 1934.94(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4250 _cell_measurement_theta_min 3.965 _cell_measurement_theta_max 65.235 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 3.122 _exptl_absorpt_correction_type 'emperical multi-scan' _exptl_absorpt_correction_T_min 0.5698 _exptl_absorpt_correction_T_max 0.8111 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Area Detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9428 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 64.91 _reflns_number_total 3127 _reflns_number_gt 2608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0347P)^2^+0.2289P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00020(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3127 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15383(9) 0.90428(10) 0.6778(2) 0.0216(3) Uani 1 1 d . . . H1 H 0.1959 0.9468 0.6732 0.030(5) Uiso 1 1 d R . . C2 C 0.07778(9) 0.91611(11) 0.5797(2) 0.0215(3) Uani 1 1 d . . . H2 H 0.0662 0.9661 0.5027 0.023(4) Uiso 1 1 d R . . C3 C 0.03037(9) 0.78815(10) 0.68303(19) 0.0204(3) Uani 1 1 d . . . H3 H -0.0143 0.7484 0.6819 0.025(4) Uiso 1 1 d R . . N1 N 0.01625(7) 0.85993(9) 0.58091(15) 0.0194(3) Uani 1 1 d . . . C4 C 0.10508(9) 0.77041(10) 0.78533(19) 0.0201(3) Uani 1 1 d . . . H4 H 0.1123 0.7166 0.8524 0.022(4) Uiso 1 1 d R . . C5 C 0.16861(9) 0.82915(10) 0.78392(19) 0.0200(3) Uani 1 1 d . . . C6 C 0.24959(9) 0.81469(11) 0.8994(2) 0.0232(4) Uani 1 1 d . . . H6A H 0.2907 0.8279 0.8310 0.030(5) Uiso 1 1 d R . . H6B H 0.2546 0.7525 0.9259 0.018(4) Uiso 1 1 d R . . C7 C 0.25768(8) 0.87031(10) 1.06540(19) 0.0189(3) Uani 1 1 d . . . H7A H 0.2503 0.9316 1.0327 0.023(4) Uiso 1 1 d R . . H7B H 0.2138 0.8576 1.1264 0.034(5) Uiso 1 1 d R . . C8 C 0.33702(9) 0.86120(10) 1.18941(19) 0.0180(3) Uani 1 1 d . . . C9 C 0.39630(9) 0.80060(11) 1.16541(19) 0.0195(3) Uani 1 1 d . . . H9 H 0.3878 0.7612 1.0666 0.014(4) Uiso 1 1 d R . . C10 C 0.46857(9) 0.79830(11) 1.28323(19) 0.0206(3) Uani 1 1 d . . . H10 H 0.5095 0.7566 1.2651 0.022(4) Uiso 1 1 d R . . N2 N 0.48465(7) 0.85210(9) 1.42190(16) 0.0212(3) Uani 1 1 d . . . C11 C 0.42665(9) 0.90991(11) 1.4459(2) 0.0215(3) Uani 1 1 d . . . H11 H 0.4410 0.9488 1.5444 0.031(5) Uiso 1 1 d R . . C12 C 0.35352(9) 0.91653(10) 1.33586(19) 0.0198(3) Uani 1 1 d . . . H12 H 0.3144 0.9595 1.3584 0.029(5) Uiso 1 1 d R . . Ca1 Ca 0.750499(14) 0.719110(18) -0.00477(3) 0.00972(11) Uani 1 1 d . . . O1 O 0.85572(6) 0.83237(7) 0.06299(12) 0.0164(2) Uani 1 1 d . . . O2 O 0.80831(5) 0.82674(6) -0.21919(12) 0.0146(2) Uani 1 1 d . . . C13 C 0.85246(8) 0.86197(9) -0.08984(17) 0.0118(3) Uani 1 1 d . . . C14 C 0.90149(8) 0.94353(10) -0.11902(18) 0.0152(3) Uani 1 1 d . . . H14A H 0.8655 0.9928 -0.1162 0.021(4) Uiso 1 1 d R . . H14B H 0.9130 0.9401 -0.2360 0.011(4) Uiso 1 1 d R . . C15 C 0.97825(8) 0.95694(10) 0.01429(18) 0.0163(3) Uani 1 1 d . . . H15A H 0.9645 0.9566 0.1295 0.023(4) Uiso 1 1 d R . . H15B H 1.0144 0.9077 0.0129 0.024(4) Uiso 1 1 d R . . O3 O 0.69338(5) 0.82718(6) 0.21016(12) 0.0145(2) Uani 1 1 d . . . O4 O 0.64579(6) 0.83461(7) -0.07193(12) 0.0182(2) Uani 1 1 d . . . C16 C 0.64941(8) 0.86326(9) 0.08190(17) 0.0120(3) Uani 1 1 d . . . C17 C 0.60010(8) 0.94455(10) 0.11391(18) 0.0146(3) Uani 1 1 d . . . H17A H 0.6369 0.9937 0.1207 0.018(4) Uiso 1 1 d R . . H17B H 0.5865 0.9381 0.2286 0.010(4) Uiso 1 1 d R . . C18 C 0.52545(8) 0.96147(9) -0.02449(18) 0.0153(3) Uani 1 1 d . . . H18A H 0.5422 0.9731 -0.1347 0.018(4) Uiso 1 1 d R . . H18B H 0.4916 0.9098 -0.0432 0.016(4) Uiso 1 1 d R . . O5 O 0.64770(5) 0.62785(7) 0.08250(12) 0.0153(2) Uani 1 1 d . . . H5OA H 0.6472 0.6304 0.1918 0.035(5) Uiso 1 1 d R . . H5OB H 0.5985 0.6358 0.0369 0.030(5) Uiso 1 1 d R . . O6 O 0.85241(5) 0.62507(7) -0.09200(12) 0.0155(2) Uani 1 1 d . . . H6OA H 0.8553 0.6307 -0.1998 0.031(5) Uiso 1 1 d R . . H6OB H 0.9012 0.6302 -0.0411 0.027(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0185(8) 0.0193(9) 0.0265(8) -0.0014(6) 0.0026(6) -0.0019(6) C2 0.0216(8) 0.0203(9) 0.0221(8) -0.0005(6) 0.0022(6) 0.0016(6) C3 0.0192(7) 0.0219(9) 0.0205(7) -0.0033(6) 0.0049(6) -0.0031(6) N1 0.0171(6) 0.0232(7) 0.0175(6) -0.0034(5) 0.0019(5) 0.0011(5) C4 0.0232(8) 0.0194(8) 0.0178(7) 0.0005(6) 0.0035(6) 0.0016(6) C5 0.0182(7) 0.0218(9) 0.0197(8) -0.0051(6) 0.0028(6) 0.0031(6) C6 0.0192(8) 0.0233(9) 0.0254(8) -0.0037(7) -0.0009(6) 0.0039(6) C7 0.0164(7) 0.0185(9) 0.0221(8) -0.0009(6) 0.0038(6) 0.0022(6) C8 0.0169(7) 0.0189(8) 0.0184(7) 0.0021(6) 0.0041(6) -0.0019(6) C9 0.0189(7) 0.0234(9) 0.0169(7) -0.0022(6) 0.0051(6) -0.0008(6) C10 0.0164(7) 0.0255(9) 0.0206(7) 0.0027(6) 0.0055(6) 0.0007(6) N2 0.0179(6) 0.0275(8) 0.0177(6) 0.0033(5) 0.0018(5) -0.0044(5) C11 0.0234(8) 0.0214(9) 0.0199(7) -0.0024(6) 0.0039(6) -0.0050(6) C12 0.0199(7) 0.0175(8) 0.0232(8) -0.0019(6) 0.0066(6) -0.0010(6) Ca1 0.00936(16) 0.01082(18) 0.00855(16) -0.00018(10) 0.00029(10) -0.00006(9) O1 0.0172(5) 0.0203(6) 0.0117(5) 0.0005(4) 0.0019(4) -0.0055(4) O2 0.0148(5) 0.0163(5) 0.0117(5) -0.0014(4) -0.0006(4) -0.0033(4) C13 0.0090(6) 0.0145(8) 0.0120(7) -0.0012(5) 0.0017(5) 0.0019(5) C14 0.0171(7) 0.0142(8) 0.0145(7) 0.0000(5) 0.0029(5) -0.0017(5) C15 0.0161(7) 0.0171(8) 0.0151(7) 0.0003(6) 0.0014(6) -0.0023(6) O3 0.0145(5) 0.0165(6) 0.0116(5) 0.0016(4) -0.0008(4) 0.0036(4) O4 0.0203(5) 0.0222(6) 0.0117(5) -0.0003(4) 0.0022(4) 0.0083(4) C16 0.0101(6) 0.0144(8) 0.0116(7) 0.0016(5) 0.0020(5) -0.0005(5) C17 0.0160(7) 0.0148(8) 0.0129(7) 0.0008(5) 0.0026(5) 0.0020(5) C18 0.0165(7) 0.0163(8) 0.0132(7) 0.0012(6) 0.0029(5) 0.0030(6) O5 0.0148(5) 0.0197(6) 0.0110(5) 0.0000(4) 0.0009(4) -0.0034(4) O6 0.0152(5) 0.0199(6) 0.0111(5) 0.0002(4) 0.0013(4) 0.0028(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 C1 C2 1.383(2) . ? C1 C5 1.397(2) . ? C1 H1 0.9601 . ? C2 N1 1.338(2) . ? C2 H2 0.9600 . ? C3 N1 1.338(2) . ? C3 C4 1.392(2) . ? C3 H3 0.9599 . ? C4 C5 1.388(2) . ? C4 H4 0.9599 . ? C5 C6 1.512(2) . ? C6 C7 1.522(2) . ? C6 H6A 0.9601 . ? C6 H6B 0.9599 . ? C7 C8 1.511(2) . ? C7 H7A 0.9601 . ? C7 H7B 0.9600 . ? C8 C9 1.387(2) . ? C8 C12 1.398(2) . ? C9 C10 1.390(2) . ? C9 H9 0.9600 . ? C10 N2 1.337(2) . ? C10 H10 0.9601 . ? N2 C11 1.344(2) . ? C11 C12 1.375(2) . ? C11 H11 0.9600 . ? C12 H12 0.9598 . ? Ca1 O3 2.3604(9) 4_575 ? Ca1 O2 2.3647(9) 4_576 ? Ca1 O5 2.3939(10) . ? Ca1 O6 2.4067(10) . ? Ca1 O1 2.4494(10) . ? Ca1 O4 2.4668(10) . ? Ca1 O2 2.6247(10) . ? Ca1 O3 2.6261(10) . ? Ca1 C13 2.8968(14) . ? Ca1 C16 2.9062(14) . ? Ca1 Ca1 3.98708(19) 4_576 ? Ca1 Ca1 3.98708(19) 4_575 ? O1 C13 1.2587(17) . ? O2 C13 1.2589(17) . ? O2 Ca1 2.3647(9) 4_575 ? C13 C14 1.5181(19) . ? C14 C15 1.5227(19) . ? C14 H14A 0.9601 . ? C14 H14B 0.9600 . ? C15 C15 1.524(3) 3_775 ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? O3 C16 1.2571(17) . ? O3 Ca1 2.3604(9) 4_576 ? O4 C16 1.2602(17) . ? C16 C17 1.5230(19) . ? C17 C18 1.5269(19) . ? C17 H17A 0.9599 . ? C17 H17B 0.9600 . ? C18 C18 1.528(3) 3_675 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? O5 H5OA 0.8500 . ? O5 H5OB 0.8501 . ? O6 H6OA 0.8500 . ? O6 H6OB 0.8500 . ? 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 C2 C1 C5 118.91(14) . . ? C2 C1 H1 120.7 . . ? C5 C1 H1 120.4 . . ? N1 C2 C1 123.88(15) . . ? N1 C2 H2 115.2 . . ? C1 C2 H2 120.9 . . ? N1 C3 C4 123.00(14) . . ? N1 C3 H3 116.1 . . ? C4 C3 H3 120.9 . . ? C2 N1 C3 117.17(13) . . ? C5 C4 C3 119.53(14) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 119.3 . . ? C4 C5 C1 117.51(14) . . ? C4 C5 C6 121.26(14) . . ? C1 C5 C6 121.17(14) . . ? C5 C6 C7 111.30(12) . . ? C5 C6 H6A 107.6 . . ? C7 C6 H6A 112.5 . . ? C5 C6 H6B 107.8 . . ? C7 C6 H6B 111.4 . . ? H6A C6 H6B 106.0 . . ? C8 C7 C6 115.46(12) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 109.7 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 104.3 . . ? C9 C8 C12 117.01(14) . . ? C9 C8 C7 123.38(14) . . ? C12 C8 C7 119.61(13) . . ? C8 C9 C10 119.68(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.2 . . ? N2 C10 C9 123.20(14) . . ? N2 C10 H10 117.6 . . ? C9 C10 H10 119.2 . . ? C10 N2 C11 116.92(13) . . ? N2 C11 C12 123.63(14) . . ? N2 C11 H11 114.5 . . ? C12 C11 H11 121.8 . . ? C11 C12 C8 119.56(14) . . ? C11 C12 H12 120.2 . . ? C8 C12 H12 120.2 . . ? O3 Ca1 O2 145.81(4) 4_575 4_576 ? O3 Ca1 O5 84.08(3) 4_575 . ? O2 Ca1 O5 76.61(3) 4_576 . ? O3 Ca1 O6 76.00(3) 4_575 . ? O2 Ca1 O6 83.83(3) 4_576 . ? O5 Ca1 O6 108.84(4) . . ? O3 Ca1 O1 124.78(3) 4_575 . ? O2 Ca1 O1 80.59(3) 4_576 . ? O5 Ca1 O1 150.34(3) . . ? O6 Ca1 O1 87.06(3) . . ? O3 Ca1 O4 81.33(3) 4_575 . ? O2 Ca1 O4 124.64(3) 4_576 . ? O5 Ca1 O4 86.70(3) . . ? O6 Ca1 O4 150.72(3) . . ? O1 Ca1 O4 90.92(4) . . ? O3 Ca1 O2 74.03(3) 4_575 . ? O2 Ca1 O2 129.53(4) 4_576 . ? O5 Ca1 O2 153.74(3) . . ? O6 Ca1 O2 80.12(3) . . ? O1 Ca1 O2 51.22(3) . . ? O4 Ca1 O2 75.97(3) . . ? O3 Ca1 O3 130.04(4) 4_575 . ? O2 Ca1 O3 73.94(3) 4_576 . ? O5 Ca1 O3 79.51(3) . . ? O6 Ca1 O3 153.89(3) . . ? O1 Ca1 O3 76.11(3) . . ? O4 Ca1 O3 51.07(3) . . ? O2 Ca1 O3 103.48(3) . . ? O3 Ca1 C13 99.70(3) 4_575 . ? O2 Ca1 C13 105.42(3) 4_576 . ? O5 Ca1 C13 167.05(4) . . ? O6 Ca1 C13 84.10(4) . . ? O1 Ca1 C13 25.52(3) . . ? O4 Ca1 C13 81.68(4) . . ? O2 Ca1 C13 25.76(3) . . ? O3 Ca1 C13 88.71(3) . . ? O3 Ca1 C16 106.09(3) 4_575 . ? O2 Ca1 C16 99.50(3) 4_576 . ? O5 Ca1 C16 83.47(4) . . ? O6 Ca1 C16 167.69(4) . . ? O1 Ca1 C16 81.84(4) . . ? O4 Ca1 C16 25.48(3) . . ? O2 Ca1 C16 88.75(3) . . ? O3 Ca1 C16 25.63(3) . . ? C13 Ca1 C16 83.59(4) . . ? O3 Ca1 Ca1 155.82(2) 4_575 4_576 ? O2 Ca1 Ca1 39.26(2) 4_576 4_576 ? O5 Ca1 Ca1 74.93(2) . 4_576 ? O6 Ca1 Ca1 121.91(2) . 4_576 ? O1 Ca1 Ca1 75.41(2) . 4_576 ? O4 Ca1 Ca1 85.55(2) . 4_576 ? O2 Ca1 Ca1 122.19(2) . 4_576 ? O3 Ca1 Ca1 34.67(2) . 4_576 ? C13 Ca1 Ca1 98.37(3) . 4_576 ? C16 Ca1 Ca1 60.25(3) . 4_576 ? O3 Ca1 Ca1 39.27(2) 4_575 4_575 ? O2 Ca1 Ca1 155.61(2) 4_576 4_575 ? O5 Ca1 Ca1 121.90(2) . 4_575 ? O6 Ca1 Ca1 75.32(2) . 4_575 ? O1 Ca1 Ca1 85.78(2) . 4_575 ? O4 Ca1 Ca1 75.40(2) . 4_575 ? O2 Ca1 Ca1 34.76(2) . 4_575 ? O3 Ca1 Ca1 122.18(2) . 4_575 ? C13 Ca1 Ca1 60.47(3) . 4_575 ? C16 Ca1 Ca1 98.45(3) . 4_575 ? Ca1 Ca1 Ca1 152.986(15) 4_576 4_575 ? C13 O1 Ca1 97.52(8) . . ? C13 O2 Ca1 164.08(9) . 4_575 ? C13 O2 Ca1 89.29(8) . . ? Ca1 O2 Ca1 105.97(3) 4_575 . ? O1 C13 O2 121.72(13) . . ? O1 C13 C14 119.31(12) . . ? O2 C13 C14 118.95(12) . . ? O1 C13 Ca1 56.96(7) . . ? O2 C13 Ca1 64.96(7) . . ? C14 C13 Ca1 173.15(9) . . ? C13 C14 C15 115.13(12) . . ? C13 C14 H14A 105.3 . . ? C15 C14 H14A 110.2 . . ? C13 C14 H14B 107.3 . . ? C15 C14 H14B 111.4 . . ? H14A C14 H14B 107.0 . . ? C14 C15 C15 112.70(15) . 3_775 ? C14 C15 H15A 108.7 . . ? C15 C15 H15A 109.7 3_775 . ? C14 C15 H15B 110.7 . . ? C15 C15 H15B 109.7 3_775 . ? H15A C15 H15B 105.1 . . ? C16 O3 Ca1 163.58(9) . 4_576 ? C16 O3 Ca1 89.73(8) . . ? Ca1 O3 Ca1 106.06(3) 4_576 . ? C16 O4 Ca1 97.14(8) . . ? O3 C16 O4 121.85(12) . . ? O3 C16 C17 118.80(12) . . ? O4 C16 C17 119.34(12) . . ? O3 C16 Ca1 64.64(7) . . ? O4 C16 Ca1 57.37(7) . . ? C17 C16 Ca1 174.14(9) . . ? C16 C17 C18 115.11(12) . . ? C16 C17 H17A 105.5 . . ? C18 C17 H17A 110.7 . . ? C16 C17 H17B 106.9 . . ? C18 C17 H17B 111.9 . . ? H17A C17 H17B 106.2 . . ? C17 C18 C18 112.31(15) . 3_675 ? C17 C18 H18A 109.0 . . ? C18 C18 H18A 110.1 3_675 . ? C17 C18 H18B 111.4 . . ? C18 C18 H18B 108.2 3_675 . ? H18A C18 H18B 105.6 . . ? Ca1 O5 H5OA 112.7 . . ? Ca1 O5 H5OB 119.9 . . ? H5OA O5 H5OB 103.6 . . ? Ca1 O6 H6OA 112.3 . . ? Ca1 O6 H6OB 119.4 . . ? H6OA O6 H6OB 103.6 . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 64.91 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.192 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.041