# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'A.W. Coleman' _publ_contact_author_address ; BioMoCeTi, UMR CNRS 7033, Universite Paris 13, 93017 Bobigny, France IBCP UMR CNRS 5086 69367 Lyon France ; _publ_contact_author_email aw.coleman@ibpc.fr _publ_contact_author_fax '33 148387625' _publ_contact_author_phone '33 148387708' _publ_requested_journal 'Chem. Comm.' # TITLE AND AUTHOR LIST _publ_section_title ; Helical Aquatubes of calix[4]arene dicarboxylic acid ; loop_ _publ_author_name _publ_author_address 'Adina N. Lazar' ; IBCP UMR CNRS 5086 69367 Lyon France ; 'Nathalie Dupont' ; BioMoCeTi, UMR CNRS 7033, Universite Paris 13, 93017 Bobigny, France ; 'Alda Navaza' ; BioMoCeTi, UMR CNRS 7033, Universite Paris 13, 93017 Bobigny, France ; 'Antony W. Coleman' ; IBCP UMR CNRS 5086 69367 Lyon France ; # Attachment 'diAcide.cif' data_c4diAacid _database_code_depnum_ccdc_archive 'CCDC 292896' _audit_creation_method SHELXL # PROCESSING SUMMARY (IUCr Office Use Only) _chemical_name_systematic ; calix[4]arene dimethoxycarboxylic acid ; _chemical_name_common 'calix[4]arene dimethoxycarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety '2(C32 H24 O8), 6.6(H2 O)' _chemical_formula_sum 'C64 H61.2 O22.6' _chemical_formula_weight 1191.92 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M r3r loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'z, x, y' 'y, z, x' _cell_length_a 20.937(2) _cell_length_b 20.937(2) _cell_length_c 20.937(2) _cell_angle_alpha 116.65(2) _cell_angle_beta 116.65(2) _cell_angle_gamma 116.65(2) _cell_volume 4265(7) _cell_formula_units_Z 3 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1878.0 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius diffractometer' _diffrn_measurement_method 'Kappa CCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20784 _diffrn_reflns_av_R_equivalents 0.22 _diffrn_reflns_av_sigmaI/netI 0.30 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4830 _reflns_number_gt 1071 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 none _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 -2(10) _refine_ls_number_reflns 4830 _refine_ls_number_parameters 336 _refine_ls_number_restraints 245 _refine_ls_R_factor_all 0.4120 _refine_ls_R_factor_gt 0.1489 _refine_ls_wR_factor_ref 0.4901 _refine_ls_wR_factor_gt 0.3759 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.077 _refine_ls_shift/su_mean 0.015 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1_1001 O 0.2553(17) 0.6110(15) 0.5166(17) 0.065(8) Uiso 1 1 d D . . H1_1001 H 0.2117 0.5676 0.4464 0.098 Uiso 1 1 calc R . . C11_1001 C 0.3081(13) 0.7206(14) 0.5836(14) 0.047(9) Uiso 1 1 d D . . C12_1001 C 0.2826(19) 0.7432(16) 0.5299(15) 0.045(9) Uiso 1 1 d D . . C13_1001 C 0.345(2) 0.8588(17) 0.6046(17) 0.029(8) Uiso 1 1 d D . . H13_1001 H 0.3394 0.8812 0.5749 0.035 Uiso 1 1 calc R . . C14_1001 C 0.414(2) 0.9393(19) 0.7221(19) 0.062(11) Uiso 1 1 d D . . H14_1001 H 0.4406 1.0084 0.7656 0.075 Uiso 1 1 calc R . . C15_1001 C 0.443(2) 0.9184(18) 0.7766(17) 0.056(11) Uiso 1 1 d D . . H15_1001 H 0.4997 0.9788 0.8596 0.067 Uiso 1 1 calc R . . C16_1001 C 0.389(2) 0.8078(18) 0.7069(16) 0.049(10) Uiso 1 1 d D . . C17_1001 C 0.412(2) 0.776(2) 0.759(2) 0.063(11) Uiso 1 1 d D . . H17A_1001 H 0.4299 0.7437 0.7358 0.075 Uiso 1 1 calc R . . H17B_1001 H 0.4845 0.8517 0.8480 0.075 Uiso 1 1 calc R . . O2_1001 O 0.2459(16) 0.5181(16) 0.5790(17) 0.053(6) Uiso 1 1 d D . . C21_1001 C 0.2297(15) 0.5646(16) 0.6306(14) 0.045(10) Uiso 1 1 d D . . C22_1001 C 0.309(2) 0.6862(18) 0.7197(19) 0.044(9) Uiso 1 1 d D . . C23_1001 C 0.283(2) 0.724(2) 0.765(2) 0.056(11) Uiso 1 1 d D . . H23_1001 H 0.3314 0.8038 0.8192 0.068 Uiso 1 1 calc R . . C24_1001 C 0.186(2) 0.643(2) 0.729(2) 0.040(9) Uiso 1 1 d D . . H24_1001 H 0.1773 0.6724 0.7679 0.048 Uiso 1 1 calc R . . C25_1001 C 0.104(2) 0.520(2) 0.635(2) 0.063(12) Uiso 1 1 d D . . H25_1001 H 0.0354 0.4642 0.6056 0.076 Uiso 1 1 calc R . . C26_1001 C 0.126(2) 0.4812(19) 0.587(2) 0.068(12) Uiso 1 1 d D . . C27_1001 C 0.0396(18) 0.3475(17) 0.4827(16) 0.038(9) Uiso 1 1 d D . . H27A_1001 H 0.0843 0.3447 0.4819 0.046 Uiso 1 1 calc R . . H27B_1001 H 0.0172 0.3145 0.5006 0.046 Uiso 1 1 calc R . . C211_1001 C 0.340(3) 0.555(3) 0.663(2) 0.092(14) Uiso 1 1 d D . . H21A_1001 H 0.3347 0.5478 0.7041 0.111 Uiso 1 1 calc R . . H21B_1001 H 0.4199 0.6377 0.7239 0.111 Uiso 1 1 calc R . . C212_1001 C 0.310(2) 0.459(2) 0.575(2) 0.16(2) Uiso 1 1 d D . . O21_1001 O 0.215(3) 0.372(3) 0.457(2) 0.29(3) Uiso 1 1 d D . . O22_1001 O 0.379(2) 0.459(2) 0.611(2) 0.089(8) Uiso 1 1 d D . . O3_1001 O 0.0363(16) 0.3469(16) 0.3459(17) 0.066(8) Uiso 1 1 d D . . H3_1001 H 0.0902 0.3836 0.4131 0.099 Uiso 1 1 calc R . . C31_1001 C -0.0745(18) 0.2688(15) 0.2920(15) 0.038(9) Uiso 1 1 d D . . C32_1001 C -0.0773(19) 0.264(2) 0.355(2) 0.041(9) Uiso 1 1 d D . . C33_1001 C -0.189(2) 0.182(3) 0.299(2) 0.071(12) Uiso 1 1 d D . . H33_1001 H -0.1955 0.1732 0.3365 0.086 Uiso 1 1 calc R . . C34_1001 C -0.290(2) 0.114(2) 0.186(2) 0.047(9) Uiso 1 1 d D . . H34_1001 H -0.3655 0.0614 0.1482 0.056 Uiso 1 1 calc R . . C35_1001 C -0.282(2) 0.121(2) 0.128(2) 0.044(9) Uiso 1 1 d D . . H35_1001 H -0.3542 0.0695 0.0489 0.052 Uiso 1 1 calc R . . C36_1001 C -0.1754(16) 0.201(2) 0.1786(19) 0.040(9) Uiso 1 1 d D . . C37_1001 C -0.169(3) 0.211(2) 0.114(2) 0.067(13) Uiso 1 1 d D . . H37A_1001 H -0.2520 0.1385 0.0278 0.081 Uiso 1 1 calc R . . H37B_1001 H -0.1217 0.2094 0.1189 0.081 Uiso 1 1 calc R . . O4_1001 O 0.0792(16) 0.4253(16) 0.2716(16) 0.049(6) Uiso 1 1 d D . . C41_1001 C 0.0062(16) 0.4280(15) 0.2435(13) 0.037(9) Uiso 1 1 d D . . C42_1001 C -0.1145(17) 0.324(2) 0.163(2) 0.058(11) Uiso 1 1 d D . . C43_1001 C -0.186(2) 0.327(2) 0.133(2) 0.049(10) Uiso 1 1 d D . . H43_1001 H -0.2674 0.2591 0.0790 0.059 Uiso 1 1 calc R . . C44_1001 C -0.1333(19) 0.433(2) 0.186(2) 0.048(9) Uiso 1 1 d D . . H44_1001 H -0.1809 0.4357 0.1654 0.058 Uiso 1 1 calc R . . C45_1001 C -0.0118(19) 0.536(2) 0.267(2) 0.052(10) Uiso 1 1 d D . . H45_1001 H 0.0201 0.6064 0.3010 0.062 Uiso 1 1 calc R . . C46_1001 C 0.0630(18) 0.5376(18) 0.301(2) 0.059(12) Uiso 1 1 d D . . C47_1001 C 0.1989(16) 0.6519(16) 0.3957(14) 0.030(8) Uiso 1 1 d D . . H47A_1001 H 0.2094 0.6938 0.3841 0.036 Uiso 1 1 calc R . . H47B_1001 H 0.2253 0.6267 0.3815 0.036 Uiso 1 1 calc R . . C411_1001 C 0.0650(18) 0.371(2) 0.186(2) 0.067(11) Uiso 1 1 d D . . H41A_1001 H 0.0351 0.3756 0.1391 0.080 Uiso 1 1 calc R . . H41B_1001 H 0.0070 0.2858 0.1295 0.080 Uiso 1 1 calc R . . C412_1001 C 0.1908(19) 0.4433(18) 0.2593(18) 0.062(9) Uiso 1 1 d D . . O41_1001 O 0.2921(19) 0.538(2) 0.3783(19) 0.133(8) Uiso 1 1 d D . . O42_1001 O 0.214(2) 0.420(3) 0.212(3) 0.133(8) Uiso 1 1 d D . . O1_1002 O 0.5770(15) 0.6749(17) 0.9319(17) 0.057(7) Uiso 1 1 d D . . H1_1002 H 0.6199 0.7445 0.9737 0.085 Uiso 1 1 calc R . . C11_1002 C 0.4695(15) 0.6103(15) 0.8829(13) 0.066(12) Uiso 1 1 d D . . C12_1002 C 0.4454(17) 0.6629(16) 0.9041(19) 0.043(9) Uiso 1 1 d D . . C13_1002 C 0.335(2) 0.594(2) 0.851(3) 0.078(14) Uiso 1 1 d D . . H13_1002 H 0.3193 0.6294 0.8679 0.094 Uiso 1 1 calc R . . C14_1002 C 0.2474(18) 0.471(2) 0.773(2) 0.059(11) Uiso 1 1 d D . . H14_1002 H 0.1695 0.4221 0.7291 0.071 Uiso 1 1 calc R . . C15_1002 C 0.2764(19) 0.4225(19) 0.760(3) 0.067(12) Uiso 1 1 d D . . H15_1002 H 0.2219 0.3443 0.7166 0.080 Uiso 1 1 calc R . . C16_1002 C 0.3869(18) 0.4909(17) 0.813(2) 0.044(10) Uiso 1 1 d D . . C17_1002 C 0.415(2) 0.436(2) 0.790(2) 0.058(11) Uiso 1 1 d D . . H17A_1002 H 0.4480 0.4575 0.7719 0.070 Uiso 1 1 calc R . . H17B_1002 H 0.3383 0.3471 0.7174 0.070 Uiso 1 1 calc R . . O2_1002 O 0.6563(16) 0.6035(16) 0.9394(16) 0.050(6) Uiso 1 1 d D . . C21_1002 C 0.6264(16) 0.5633(15) 0.9702(15) 0.052(11) Uiso 1 1 d D . . C22_1002 C 0.5042(18) 0.473(2) 0.894(2) 0.053(10) Uiso 1 1 d D . . C23_1002 C 0.468(2) 0.427(3) 0.918(2) 0.069(12) Uiso 1 1 d D . . H23_1002 H 0.3866 0.3641 0.8663 0.083 Uiso 1 1 calc R . . C24_1002 C 0.559(2) 0.480(2) 1.023(3) 0.061(12) Uiso 1 1 d D . . H24_1002 H 0.5393 0.4557 1.0456 0.074 Uiso 1 1 calc R . . C25_1002 C 0.678(2) 0.566(2) 1.096(2) 0.060(12) Uiso 1 1 d D . . H25_1002 H 0.7345 0.5945 1.1641 0.073 Uiso 1 1 calc R . . C26_1002 C 0.7171(18) 0.611(2) 1.0729(19) 0.033(8) Uiso 1 1 d D . . C27_1002 C 0.8500(18) 0.7137(18) 1.160(2) 0.059(12) Uiso 1 1 d D . . H27A_1002 H 0.8548 0.7120 1.1152 0.071 Uiso 1 1 calc R . . H27B_1002 H 0.8843 0.6990 1.1878 0.071 Uiso 1 1 calc R . . C211_1002 C 0.6635(19) 0.5550(19) 0.874(2) 0.061(10) Uiso 1 1 d D . . H21A_1002 H 0.5912 0.5000 0.7903 0.073 Uiso 1 1 calc R . . H21B_1002 H 0.6584 0.5053 0.8716 0.073 Uiso 1 1 calc R . . C212_1002 C 0.7764(19) 0.6441(18) 0.9205(18) 0.083(12) Uiso 1 1 d D . . O21_1002 O 0.8651(18) 0.7627(17) 1.0188(19) 0.088(8) Uiso 1 1 d D . . O22_1002 O 0.787(2) 0.605(3) 0.864(3) 0.140(13) Uiso 1 1 d D . . O3_1002 O 0.8509(17) 0.8594(17) 1.1657(16) 0.054(7) Uiso 1 1 d D . . H3_1002 H 0.8129 0.7924 1.1085 0.081 Uiso 1 1 calc R . . C31_1002 C 0.9255(17) 0.9051(18) 1.271(2) 0.072(13) Uiso 1 1 d D . . C32_1002 C 0.929(2) 0.842(2) 1.272(2) 0.049(10) Uiso 1 1 d D . . C33_1002 C 1.010(2) 0.904(2) 1.3872(19) 0.043(9) Uiso 1 1 d D . . H33_1002 H 1.0140 0.8631 1.3916 0.051 Uiso 1 1 calc R . . C34_1002 C 1.087(3) 1.020(2) 1.497(2) 0.073(13) Uiso 1 1 d D . . H34_1002 H 1.1433 1.0564 1.5708 0.087 Uiso 1 1 calc R . . C35_1002 C 1.077(2) 1.079(2) 1.491(2) 0.062(11) Uiso 1 1 d D . . H35_1002 H 1.1215 1.1540 1.5603 0.074 Uiso 1 1 calc R . . C36_1002 C 0.996(2) 1.021(2) 1.3772(18) 0.059(11) Uiso 1 1 d D . . C37_1002 C 0.985(2) 1.081(2) 1.363(2) 0.053(11) Uiso 1 1 d D . . H37A_1002 H 0.9832 1.0698 1.3118 0.064 Uiso 1 1 calc R . . H37B_1002 H 1.0563 1.1686 1.4430 0.064 Uiso 1 1 calc R . . O4_1002 O 0.7811(18) 0.9338(18) 1.1220(18) 0.064(8) Uiso 1 1 d D . . C41_1002 C 0.7693(16) 0.9520(14) 1.1864(18) 0.064(12) Uiso 1 1 d D . . C42_1002 C 0.870(2) 1.030(2) 1.3063(19) 0.061(12) Uiso 1 1 d D . . C43_1002 C 0.857(2) 1.049(3) 1.369(2) 0.054(11) Uiso 1 1 d D . . H43_1002 H 0.9229 1.1025 1.4507 0.065 Uiso 1 1 calc R . . C44_1002 C 0.748(2) 0.992(3) 1.315(2) 0.081(14) Uiso 1 1 d D . . H44_1002 H 0.7421 1.0065 1.3593 0.097 Uiso 1 1 calc R . . C45_1002 C 0.647(2) 0.914(2) 1.193(2) 0.052(11) Uiso 1 1 d D . . H45_1002 H 0.5751 0.8778 1.1572 0.062 Uiso 1 1 calc R . . C46_1002 C 0.6580(19) 0.891(2) 1.1279(19) 0.046(10) Uiso 1 1 d D . . C47_1002 C 0.5412(19) 0.7982(17) 0.9932(19) 0.073(13) Uiso 1 1 d D . . H47A_1002 H 0.5030 0.8136 0.9882 0.088 Uiso 1 1 calc R . . H47B_1002 H 0.5648 0.8129 0.9658 0.088 Uiso 1 1 calc R . . C411_1002 C 0.793(3) 0.993(2) 1.105(3) 0.055(10) Uiso 1 1 d D . . H41A_1002 H 0.8506 1.0777 1.1791 0.066 Uiso 0.50 1 calc PR . . H41B_1002 H 0.7143 0.9504 1.0388 0.066 Uiso 0.50 1 calc PR . . C412_1002 C 0.841(3) 0.984(3) 1.070(3) 0.133(15) Uiso 0.50 1 d PD . . O41_1002 O 0.867(4) 0.938(5) 1.065(4) 0.133(15) Uiso 0.50 1 d PD . . O42_1002 O 0.864(4) 1.022(4) 1.039(4) 0.133(15) Uiso 0.50 1 d PD . . O5W_1004 O 0.854(4) 0.917(4) 0.664(4) 0.179(16) Uiso 1 1 d . . . O4W_1004 O 0.755(3) 0.807(3) 0.726(3) 0.169(14) Uiso 1 1 d . . . O8W_1004 O 1.258(4) 1.281(4) 1.194(4) 0.114(13) Uiso 0.70 1 d P . . O9W_1004 O 1.147(8) 1.097(8) 1.029(8) 0.09(3) Uiso 0.30 1 d P . . O6W_1004 O 0.351(5) 0.351(5) 0.351(5) 0.13(2) Uiso 0.90 3 d SP . . _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1_1001 C11_1001 1.380(14) . ? C11_1001 C12_1001 1.392(14) . ? C11_1001 C16_1001 1.394(14) . ? C12_1001 C13_1001 1.396(15) . ? C12_1001 C47_1001 1.543(15) . ? C13_1001 C14_1001 1.375(15) . ? C14_1001 C15_1001 1.390(15) . ? C15_1001 C16_1001 1.382(15) . ? C16_1001 C17_1001 1.521(16) . ? C17_1001 C22_1001 1.499(17) . ? O2_1001 C211_1001 1.374(18) . ? O2_1001 C21_1001 1.383(16) . ? C21_1001 C22_1001 1.374(16) . ? C21_1001 C26_1001 1.408(16) . ? C22_1001 C23_1001 1.404(17) . ? C23_1001 C24_1001 1.398(17) . ? C24_1001 C25_1001 1.386(16) . ? C25_1001 C26_1001 1.380(17) . ? C26_1001 C27_1001 1.520(17) . ? C27_1001 C32_1001 1.514(17) . ? C211_1001 C212_1001 1.522(14) . ? C212_1001 O21_1001 1.295(14) . ? C212_1001 O22_1001 1.296(13) . ? O3_1001 C31_1001 1.386(16) . ? C31_1001 C36_1001 1.375(16) . ? C31_1001 C32_1001 1.394(16) . ? C32_1001 C33_1001 1.390(17) . ? C33_1001 C34_1001 1.373(17) . ? C34_1001 C35_1001 1.368(15) . ? C35_1001 C36_1001 1.358(16) . ? C36_1001 C37_1001 1.511(16) . ? C37_1001 C42_1001 1.518(17) . ? O4_1001 C411_1001 1.407(17) . ? O4_1001 C41_1001 1.409(16) . ? C41_1001 C42_1001 1.385(16) . ? C41_1001 C46_1001 1.389(16) . ? C42_1001 C43_1001 1.389(17) . ? C43_1001 C44_1001 1.373(17) . ? C44_1001 C45_1001 1.383(16) . ? C45_1001 C46_1001 1.382(16) . ? C46_1001 C47_1001 1.525(16) . ? C411_1001 C412_1001 1.517(13) . ? C412_1001 O42_1001 1.285(13) . ? C412_1001 O41_1001 1.301(13) . ? O1_1002 C11_1002 1.380(14) . ? C11_1002 C12_1002 1.387(14) . ? C11_1002 C16_1002 1.400(14) . ? C12_1002 C13_1002 1.392(15) . ? C12_1002 C47_1002 1.530(16) . ? C13_1002 C14_1002 1.395(16) . ? C14_1002 C15_1002 1.394(16) . ? C15_1002 C16_1002 1.391(15) . ? C16_1002 C17_1002 1.508(16) . ? C17_1002 C22_1002 1.524(17) . ? O2_1002 C21_1002 1.377(16) . ? O2_1002 C211_1002 1.412(17) . ? C21_1002 C26_1002 1.390(16) . ? C21_1002 C22_1002 1.397(16) . ? C22_1002 C23_1002 1.379(17) . ? C23_1002 C24_1002 1.364(18) . ? C24_1002 C25_1002 1.368(16) . ? C25_1002 C26_1002 1.373(17) . ? C26_1002 C27_1002 1.502(17) . ? C27_1002 C32_1002 1.527(17) . ? C211_1002 C212_1002 1.541(13) . ? C212_1002 O22_1002 1.298(13) . ? C212_1002 O21_1002 1.306(13) . ? O3_1002 C31_1002 1.384(17) . ? C31_1002 C32_1002 1.362(16) . ? C31_1002 C36_1002 1.415(17) . ? C32_1002 C33_1002 1.391(17) . ? C33_1002 C34_1002 1.391(18) . ? C34_1002 C35_1002 1.397(16) . ? C35_1002 C36_1002 1.400(17) . ? C36_1002 C37_1002 1.510(17) . ? C37_1002 C42_1002 1.515(17) . ? O4_1002 C411_1002 1.397(17) . ? O4_1002 C41_1002 1.395(16) . ? C41_1002 C42_1002 1.383(17) . ? C41_1002 C46_1002 1.391(16) . ? C42_1002 C43_1002 1.391(17) . ? C43_1002 C44_1002 1.384(18) . ? C44_1002 C45_1002 1.393(16) . ? C45_1002 C46_1002 1.394(17) . ? C46_1002 C47_1002 1.531(17) . ? C411_1002 C412_1002 1.522(14) . ? C412_1002 O42_1002 1.282(14) . ? C412_1002 O41_1002 1.287(14) . ? 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_1001 C11_1001 C12_1001 121.0(13) . . ? O1_1001 C11_1001 C16_1001 117.2(13) . . ? C12_1001 C11_1001 C16_1001 121.8(11) . . ? C11_1001 C12_1001 C13_1001 118.0(12) . . ? C11_1001 C12_1001 C47_1001 123.3(14) . . ? C13_1001 C12_1001 C47_1001 118.4(14) . . ? C14_1001 C13_1001 C12_1001 119.8(13) . . ? C13_1001 C14_1001 C15_1001 120.6(13) . . ? C16_1001 C15_1001 C14_1001 119.8(13) . . ? C15_1001 C16_1001 C11_1001 118.8(12) . . ? C15_1001 C16_1001 C17_1001 122.3(16) . . ? C11_1001 C16_1001 C17_1001 118.9(15) . . ? C22_1001 C17_1001 C16_1001 116(2) . . ? C211_1001 O2_1001 C21_1001 107.9(15) . . ? C22_1001 C21_1001 O2_1001 122.6(16) . . ? C22_1001 C21_1001 C26_1001 120.2(19) . . ? O2_1001 C21_1001 C26_1001 117.2(14) . . ? C21_1001 C22_1001 C23_1001 118(2) . . ? C21_1001 C22_1001 C17_1001 122.9(17) . . ? C23_1001 C22_1001 C17_1001 118.5(18) . . ? C24_1001 C23_1001 C22_1001 122(2) . . ? C25_1001 C24_1001 C23_1001 119.1(16) . . ? C26_1001 C25_1001 C24_1001 119.3(17) . . ? C25_1001 C26_1001 C21_1001 121.1(19) . . ? C25_1001 C26_1001 C27_1001 122.6(18) . . ? C21_1001 C26_1001 C27_1001 116.2(15) . . ? C32_1001 C27_1001 C26_1001 116(2) . . ? O2_1001 C211_1001 C212_1001 98.0(18) . . ? O21_1001 C212_1001 O22_1001 113(3) . . ? O21_1001 C212_1001 C211_1001 123.7(17) . . ? O22_1001 C212_1001 C211_1001 123.2(17) . . ? C36_1001 C31_1001 O3_1001 117.4(14) . . ? C36_1001 C31_1001 C32_1001 123.9(18) . . ? O3_1001 C31_1001 C32_1001 118.6(15) . . ? C31_1001 C32_1001 C33_1001 119(2) . . ? C31_1001 C32_1001 C27_1001 120.4(17) . . ? C33_1001 C32_1001 C27_1001 120.8(17) . . ? C34_1001 C33_1001 C32_1001 117(2) . . ? C35_1001 C34_1001 C33_1001 121.3(17) . . ? C36_1001 C35_1001 C34_1001 123.5(17) . . ? C35_1001 C36_1001 C31_1001 114.9(18) . . ? C35_1001 C36_1001 C37_1001 122.0(18) . . ? C31_1001 C36_1001 C37_1001 123.1(17) . . ? C36_1001 C37_1001 C42_1001 116(2) . . ? C411_1001 O4_1001 C41_1001 116.4(13) . . ? C42_1001 C41_1001 C46_1001 125.1(18) . . ? C42_1001 C41_1001 O4_1001 118.8(15) . . ? C46_1001 C41_1001 O4_1001 116.1(14) . . ? C41_1001 C42_1001 C43_1001 118(2) . . ? C41_1001 C42_1001 C37_1001 123.8(18) . . ? C43_1001 C42_1001 C37_1001 118.2(18) . . ? C44_1001 C43_1001 C42_1001 119(2) . . ? C43_1001 C44_1001 C45_1001 122.1(17) . . ? C46_1001 C45_1001 C44_1001 121.3(17) . . ? C45_1001 C46_1001 C41_1001 115.1(18) . . ? C45_1001 C46_1001 C47_1001 122.6(17) . . ? C41_1001 C46_1001 C47_1001 122.3(15) . . ? C46_1001 C47_1001 C12_1001 114.2(19) . . ? O4_1001 C411_1001 C412_1001 106.6(16) . . ? O42_1001 C412_1001 O41_1001 109(2) . . ? O42_1001 C412_1001 C411_1001 124.7(15) . . ? O41_1001 C412_1001 C411_1001 126.3(16) . . ? O1_1002 C11_1002 C12_1002 121.1(13) . . ? O1_1002 C11_1002 C16_1002 117.7(13) . . ? C12_1002 C11_1002 C16_1002 121.2(12) . . ? C11_1002 C12_1002 C13_1002 119.4(12) . . ? C11_1002 C12_1002 C47_1002 121.9(16) . . ? C13_1002 C12_1002 C47_1002 118.4(16) . . ? C12_1002 C13_1002 C14_1002 119.6(13) . . ? C13_1002 C14_1002 C15_1002 120.3(13) . . ? C16_1002 C15_1002 C14_1002 120.0(13) . . ? C15_1002 C16_1002 C11_1002 118.9(12) . . ? C15_1002 C16_1002 C17_1002 121.2(16) . . ? C11_1002 C16_1002 C17_1002 119.8(15) . . ? C16_1002 C17_1002 C22_1002 117(2) . . ? C21_1002 O2_1002 C211_1002 120.8(13) . . ? O2_1002 C21_1002 C26_1002 119.0(15) . . ? O2_1002 C21_1002 C22_1002 117.4(15) . . ? C26_1002 C21_1002 C22_1002 123.5(19) . . ? C23_1002 C22_1002 C21_1002 120(2) . . ? C23_1002 C22_1002 C17_1002 120.7(19) . . ? C21_1002 C22_1002 C17_1002 119.0(17) . . ? C24_1002 C23_1002 C22_1002 116(2) . . ? C23_1002 C24_1002 C25_1002 124.0(18) . . ? C24_1002 C25_1002 C26_1002 121.9(17) . . ? C25_1002 C26_1002 C21_1002 114.5(18) . . ? C25_1002 C26_1002 C27_1002 121.8(18) . . ? C21_1002 C26_1002 C27_1002 123.4(16) . . ? C26_1002 C27_1002 C32_1002 115(2) . . ? O2_1002 C211_1002 C212_1002 118.9(16) . . ? O22_1002 C212_1002 O21_1002 117(2) . . ? O22_1002 C212_1002 C211_1002 121.6(15) . . ? O21_1002 C212_1002 C211_1002 121.2(15) . . ? C32_1002 C31_1002 O3_1002 121.8(16) . . ? C32_1002 C31_1002 C36_1002 123(2) . . ? O3_1002 C31_1002 C36_1002 114.9(15) . . ? C31_1002 C32_1002 C33_1002 113(2) . . ? C31_1002 C32_1002 C27_1002 125.8(18) . . ? C33_1002 C32_1002 C27_1002 121.1(18) . . ? C32_1002 C33_1002 C34_1002 128(2) . . ? C33_1002 C34_1002 C35_1002 117.5(17) . . ? C34_1002 C35_1002 C36_1002 117.4(16) . . ? C35_1002 C36_1002 C31_1002 121.1(18) . . ? C35_1002 C36_1002 C37_1002 121.7(18) . . ? C31_1002 C36_1002 C37_1002 117.1(16) . . ? C36_1002 C37_1002 C42_1002 113(2) . . ? C411_1002 O4_1002 C41_1002 116.3(16) . . ? C42_1002 C41_1002 O4_1002 117.5(15) . . ? C42_1002 C41_1002 C46_1002 123(2) . . ? O4_1002 C41_1002 C46_1002 119.3(16) . . ? C41_1002 C42_1002 C43_1002 116(2) . . ? C41_1002 C42_1002 C37_1002 122.5(17) . . ? C43_1002 C42_1002 C37_1002 121.4(19) . . ? C44_1002 C43_1002 C42_1002 122(2) . . ? C43_1002 C44_1002 C45_1002 120.6(17) . . ? C44_1002 C45_1002 C46_1002 118.0(16) . . ? C41_1002 C46_1002 C45_1002 119.7(19) . . ? C41_1002 C46_1002 C47_1002 125.2(17) . . ? C45_1002 C46_1002 C47_1002 115.0(18) . . ? C12_1002 C47_1002 C46_1002 116(2) . . ? O4_1002 C411_1002 C412_1002 99.7(19) . . ? O42_1002 C412_1002 O41_1002 107(3) . . ? O42_1002 C412_1002 C411_1002 125.4(19) . . ? O41_1002 C412_1002 C411_1002 127.1(19) . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.819 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.157