# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'P. D. Beer' 'Andrew R. Cowley' 'Michael Lankshear' _publ_contact_author_name 'Paul Beer' _publ_contact_author_address ; Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UNITED KINGDOM ; _publ_contact_author_email PAUL.BEER@CHEM.OX.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Cooperative AND receptors for ion-pairs ; # Attachment 'arc1262.cif' data_arc1262 _database_code_depnum_ccdc_archive 'CCDC 289857' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Oxford Diffraction Gemini ; _diffrn_radiation_monochromator graphite _computing_data_collection ; Gemini software 'Crysalis CCD' (Oxford Diffraction, 2005) ; _computing_data_reduction ; Gemini software 'Crysalis RED' (Oxford Diffraction, 2005) ; _computing_cell_refinement ; Gemini software 'Crysalis RED' (Oxford Diffraction, 2005) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #============================================================= _cell_length_a 10.0261(3) _cell_angle_alpha 102.137(3) _cell_length_b 12.5372(4) _cell_angle_beta 94.601(3) _cell_length_c 20.4416(6) _cell_angle_gamma 101.430(3) _cell_volume 2442.24(14) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C54 H59 N3 O10 ' _chemical_formula_moiety ' C52 H56 N2 O10, C2 H3 N ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 910.08 _cell_measurement_reflns_used 6715 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.085 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 22001 _reflns_number_total 11760 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_theta_min 4.509 _diffrn_reflns_theta_max 28.084 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _refine_diff_density_min -0.37 _refine_diff_density_max 0.47 _refine_ls_number_reflns 5735 _refine_ls_number_restraints 0 _refine_ls_number_parameters 612 #_refine_ls_R_factor_ref 0.0447 _refine_ls_wR_factor_ref 0.0514 _refine_ls_goodness_of_fit_ref 1.1318 #_reflns_number_all 11760 _refine_ls_R_factor_all 0.1025 _refine_ls_wR_factor_all 0.0669 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 5735 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_gt 0.0514 _refine_ls_shift/su_max 0.000502 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 13.5 -6.15 11.3 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type C1 C 0.3698(2) 0.21942(18) 0.39791(11) 0.0311 1.0000 Uani C2 C 0.3656(2) 0.30909(17) 0.45839(10) 0.0312 1.0000 Uani C3 C 0.3865(2) 0.29013(19) 0.51986(10) 0.0358 1.0000 Uani C4 C 0.4068(2) 0.1816(2) 0.52978(11) 0.0380 1.0000 Uani C5 C 0.3907(2) 0.08944(19) 0.46994(12) 0.0357 1.0000 Uani C6 C 0.3760(2) 0.10508(17) 0.40702(11) 0.0309 1.0000 Uani C7 C 0.3781(2) 0.01705(18) 0.34491(11) 0.0351 1.0000 Uani C8 C 0.2353(2) -0.00138(16) 0.23419(10) 0.0312 1.0000 Uani C9 C 0.2445(2) -0.02268(17) 0.29814(11) 0.0324 1.0000 Uani C10 C 0.1301(2) -0.08674(18) 0.31746(11) 0.0337 1.0000 Uani C11 C 0.0075(2) -0.12943(17) 0.27476(11) 0.0335 1.0000 Uani C12 C 0.0004(2) -0.10085(18) 0.21253(11) 0.0351 1.0000 Uani C13 C 0.1112(2) -0.03762(17) 0.19114(10) 0.0334 1.0000 Uani C14 C 0.0990(2) -0.00748(18) 0.12305(11) 0.0377 1.0000 Uani C15 C 0.0423(2) 0.18262(18) 0.16736(10) 0.0320 1.0000 Uani C16 C 0.1315(2) 0.11702(17) 0.12898(10) 0.0323 1.0000 Uani C17 C 0.2349(2) 0.17025(18) 0.10249(11) 0.0349 1.0000 Uani C18 C 0.2672(2) 0.29229(19) 0.11335(10) 0.0345 1.0000 Uani C19 C 0.1886(2) 0.35611(18) 0.15745(11) 0.0360 1.0000 Uani C20 C 0.0841(2) 0.30708(18) 0.18472(10) 0.0316 1.0000 Uani C21 C 0.0052(2) 0.3713(2) 0.23244(11) 0.0380 1.0000 Uani C22 C 0.1589(2) 0.40267(17) 0.34214(10) 0.0322 1.0000 Uani C23 C 0.0318(2) 0.35661(19) 0.30383(11) 0.0343 1.0000 Uani C24 C -0.0689(2) 0.2922(2) 0.33118(11) 0.0383 1.0000 Uani C25 C -0.0465(2) 0.2742(2) 0.39563(11) 0.0386 1.0000 Uani C26 C 0.0824(2) 0.3216(2) 0.43187(11) 0.0367 1.0000 Uani C27 C 0.1871(2) 0.38333(18) 0.40591(10) 0.0322 1.0000 Uani C28 C 0.3314(2) 0.41427(18) 0.44394(11) 0.0345 1.0000 Uani O1 O 0.37034(18) 0.23906(13) 0.34210(8) 0.0434 1.0000 Uani O2 O 0.4380(2) 0.16729(16) 0.58612(8) 0.0548 1.0000 Uani O3 O -0.06432(16) 0.13436(14) 0.18327(8) 0.0432 1.0000 Uani O4 O 0.36203(17) 0.34107(13) 0.08775(8) 0.0431 1.0000 Uani O5 O 0.34969(15) 0.05596(12) 0.21186(7) 0.0355 1.0000 Uani C29 C 0.4346(3) -0.01846(19) 0.18445(12) 0.0404 1.0000 Uani C30 C 0.5646(3) 0.0458(2) 0.16850(12) 0.0425 1.0000 Uani O6 O 0.53970(17) 0.08893(15) 0.11100(8) 0.0446 1.0000 Uani C31 C 0.6584(3) 0.1048(2) 0.07748(13) 0.0490 1.0000 Uani C32 C 0.6321(3) 0.1614(2) 0.02128(12) 0.0482 1.0000 Uani N1 N 0.6399(2) 0.28067(17) 0.04475(10) 0.0414 1.0000 Uani C33 C 0.7594(3) 0.3555(2) 0.05079(12) 0.0458 1.0000 Uani O7 O 0.8681(2) 0.32595(19) 0.04389(11) 0.0712 1.0000 Uani C34 C 0.6382(2) 0.51735(19) 0.07725(11) 0.0368 1.0000 Uani C35 C 0.7542(2) 0.4768(2) 0.06199(11) 0.0416 1.0000 Uani C36 C 0.8694(3) 0.5513(3) 0.05212(13) 0.0552 1.0000 Uani C37 C 0.8675(3) 0.6618(3) 0.05453(14) 0.0600 1.0000 Uani C38 C 0.7516(3) 0.7006(2) 0.06875(12) 0.0497 1.0000 Uani C39 C 0.6358(2) 0.6290(2) 0.08118(10) 0.0385 1.0000 Uani C40 C 0.5153(3) 0.6775(2) 0.09847(11) 0.0397 1.0000 Uani O8 O 0.5234(2) 0.77910(14) 0.10666(10) 0.0537 1.0000 Uani N2 N 0.3986(2) 0.60818(18) 0.10460(10) 0.0386 1.0000 Uani C41 C 0.2782(3) 0.6515(2) 0.12124(12) 0.0431 1.0000 Uani C42 C 0.2856(3) 0.7038(2) 0.19543(13) 0.0480 1.0000 Uani O9 O 0.2680(2) 0.61782(13) 0.23149(8) 0.0519 1.0000 Uani C43 C 0.3257(4) 0.6501(2) 0.29833(15) 0.0719 1.0000 Uani C44 C 0.2690(4) 0.5840(2) 0.34030(14) 0.0786 1.0000 Uani O10 O 0.25930(17) 0.46600(12) 0.31448(8) 0.0401 1.0000 Uani C45 C -0.1137(2) -0.2111(2) 0.29182(11) 0.0411 1.0000 Uani C46 C -0.0964(3) -0.2186(3) 0.36554(13) 0.0565 1.0000 Uani C47 C -0.1188(3) -0.3279(2) 0.24776(14) 0.0565 1.0000 Uani C48 C -0.2487(3) -0.1770(3) 0.27666(14) 0.0577 1.0000 Uani C49 C -0.1543(2) 0.2013(3) 0.42615(12) 0.0498 1.0000 Uani C50 C -0.2820(3) 0.1436(3) 0.37580(16) 0.0686 1.0000 Uani C51 C -0.1956(4) 0.2728(3) 0.48793(17) 0.0790 1.0000 Uani C52 C -0.0924(3) 0.1092(3) 0.44737(15) 0.0625 1.0000 Uani N3 N 0.6592(3) 0.4729(3) 0.36313(17) 0.0883 1.0000 Uani C53 C 0.6051(3) 0.4267(3) 0.31115(17) 0.0618 1.0000 Uani C54 C 0.5345(4) 0.3665(3) 0.24523(16) 0.0786 1.0000 Uani H1 H 0.557(3) 0.300(2) 0.0485(14) 0.059(8) 1.0000 Uiso H2 H 0.394(3) 0.537(2) 0.0991(12) 0.040(7) 1.0000 Uiso H31 H 0.3883 0.3516 0.5602 0.0412 1.0000 Uiso H51 H 0.3907 0.0125 0.4763 0.0433 1.0000 Uiso H71 H 0.4016 -0.0490 0.3595 0.0419 1.0000 Uiso H72 H 0.4509 0.0484 0.3191 0.0419 1.0000 Uiso H101 H 0.1368 -0.1023 0.3635 0.0402 1.0000 Uiso H121 H -0.0883 -0.1270 0.1819 0.0397 1.0000 Uiso H141 H 0.1641 -0.0411 0.0951 0.0433 1.0000 Uiso H142 H 0.0030 -0.0392 0.1003 0.0433 1.0000 Uiso H171 H 0.2915 0.1258 0.0746 0.0419 1.0000 Uiso H191 H 0.2143 0.4397 0.1675 0.0429 1.0000 Uiso H211 H 0.0333 0.4526 0.2328 0.0476 1.0000 Uiso H212 H -0.0951 0.3440 0.2162 0.0476 1.0000 Uiso H241 H -0.1601 0.2577 0.3036 0.0474 1.0000 Uiso H261 H 0.1005 0.3107 0.4786 0.0451 1.0000 Uiso H281 H 0.3351 0.4702 0.4872 0.0400 1.0000 Uiso H282 H 0.3983 0.4466 0.4157 0.0400 1.0000 Uiso H291 H 0.4566 -0.0617 0.2182 0.0491 1.0000 Uiso H292 H 0.3836 -0.0714 0.1422 0.0491 1.0000 Uiso H301 H 0.6299 -0.0048 0.1594 0.0527 1.0000 Uiso H302 H 0.6058 0.1092 0.2080 0.0527 1.0000 Uiso H311 H 0.7379 0.1526 0.1102 0.0633 1.0000 Uiso H312 H 0.6795 0.0306 0.0585 0.0633 1.0000 Uiso H321 H 0.7020 0.1510 -0.0104 0.0604 1.0000 Uiso H322 H 0.5383 0.1253 -0.0032 0.0604 1.0000 Uiso H341 H 0.5552 0.4654 0.0855 0.0424 1.0000 Uiso H361 H 0.9550 0.5243 0.0431 0.0603 1.0000 Uiso H371 H 0.9504 0.7136 0.0459 0.0651 1.0000 Uiso H381 H 0.7503 0.7806 0.0702 0.0555 1.0000 Uiso H411 H 0.2693 0.7094 0.0952 0.0552 1.0000 Uiso H412 H 0.1955 0.5885 0.1079 0.0552 1.0000 Uiso H421 H 0.3770 0.7559 0.2118 0.0608 1.0000 Uiso H422 H 0.2114 0.7462 0.2027 0.0608 1.0000 Uiso H431 H 0.3156 0.7282 0.3166 0.0821 1.0000 Uiso H432 H 0.4253 0.6489 0.2998 0.0821 1.0000 Uiso H441 H 0.3274 0.6079 0.3851 0.0888 1.0000 Uiso H442 H 0.1746 0.5962 0.3462 0.0888 1.0000 Uiso H461 H -0.1773 -0.2724 0.3741 0.0663 1.0000 Uiso H462 H -0.0109 -0.2452 0.3752 0.0663 1.0000 Uiso H463 H -0.0897 -0.1431 0.3955 0.0663 1.0000 Uiso H471 H -0.1967 -0.3831 0.2577 0.0646 1.0000 Uiso H472 H -0.0307 -0.3506 0.2579 0.0646 1.0000 Uiso H473 H -0.1324 -0.3260 0.1991 0.0646 1.0000 Uiso H481 H -0.3258 -0.2311 0.2881 0.0679 1.0000 Uiso H482 H -0.2445 -0.1002 0.3043 0.0679 1.0000 Uiso H483 H -0.2643 -0.1775 0.2277 0.0679 1.0000 Uiso H501 H -0.3491 0.0971 0.3979 0.0817 1.0000 Uiso H502 H -0.3247 0.2013 0.3606 0.0817 1.0000 Uiso H503 H -0.2556 0.0945 0.3359 0.0817 1.0000 Uiso H511 H -0.2659 0.2250 0.5077 0.0982 1.0000 Uiso H512 H -0.1130 0.3069 0.5222 0.0982 1.0000 Uiso H513 H -0.2349 0.3334 0.4744 0.0982 1.0000 Uiso H521 H -0.1621 0.0611 0.4674 0.0747 1.0000 Uiso H522 H -0.0100 0.1441 0.4816 0.0747 1.0000 Uiso H523 H -0.0650 0.0622 0.4070 0.0747 1.0000 Uiso H541 H 0.4660 0.4076 0.2304 0.0912 1.0000 Uiso H542 H 0.6025 0.3605 0.2122 0.0912 1.0000 Uiso H543 H 0.4861 0.2898 0.2476 0.0912 1.0000 Uiso 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 0.0233(10) 0.0328(11) 0.0346(11) 0.0079(9) 0.0002(8) 0.0012(8) C2 0.0259(11) 0.0327(11) 0.0312(11) 0.0066(9) 0.0001(8) -0.0001(9) C3 0.0319(12) 0.0423(13) 0.0287(11) 0.0049(9) 0.0016(9) 0.0023(10) C4 0.0315(12) 0.0492(14) 0.0353(12) 0.0161(10) 0.0030(9) 0.0070(10) C5 0.0283(11) 0.0365(12) 0.0434(13) 0.0151(10) 0.0020(9) 0.0046(9) C6 0.0217(10) 0.0329(11) 0.0364(11) 0.0088(9) -0.0001(8) 0.0029(8) C7 0.0335(12) 0.0313(11) 0.0400(12) 0.0079(9) 0.0010(9) 0.0079(9) C8 0.0350(12) 0.0213(10) 0.0349(11) 0.0036(8) 0.0075(9) 0.0021(9) C9 0.0347(12) 0.0259(10) 0.0342(11) 0.0032(9) 0.0024(9) 0.0058(9) C10 0.0402(12) 0.0296(11) 0.0307(11) 0.0062(9) 0.0057(9) 0.0065(9) C11 0.0374(12) 0.0288(11) 0.0320(11) 0.0049(9) 0.0077(9) 0.0032(9) C12 0.0383(12) 0.0314(11) 0.0296(11) 0.0036(9) -0.0004(9) -0.0010(9) C13 0.0418(13) 0.0255(10) 0.0305(11) 0.0039(8) 0.0048(9) 0.0044(9) C14 0.0460(13) 0.0312(12) 0.0309(11) 0.0038(9) 0.0036(10) 0.0012(10) C15 0.0299(11) 0.0380(12) 0.0259(10) 0.0100(9) -0.0026(8) 0.0020(9) C16 0.0375(12) 0.0319(11) 0.0239(10) 0.0053(8) 0.0006(9) 0.0019(9) C17 0.0374(12) 0.0363(12) 0.0311(11) 0.0077(9) 0.0066(9) 0.0077(10) C18 0.0353(12) 0.0378(12) 0.0295(11) 0.0111(9) 0.0016(9) 0.0037(10) C19 0.0434(13) 0.0332(11) 0.0306(11) 0.0075(9) 0.0031(9) 0.0073(10) C20 0.0331(11) 0.0374(12) 0.0252(10) 0.0095(9) -0.0017(8) 0.0094(9) C21 0.0403(13) 0.0463(13) 0.0323(11) 0.0121(10) 0.0048(9) 0.0178(10) C22 0.0402(13) 0.0280(11) 0.0307(11) 0.0058(9) 0.0085(9) 0.0122(9) C23 0.0370(12) 0.0401(12) 0.0301(11) 0.0072(9) 0.0069(9) 0.0187(10) C24 0.0291(12) 0.0543(14) 0.0350(12) 0.0096(10) 0.0071(9) 0.0168(10) C25 0.0314(12) 0.0551(14) 0.0341(12) 0.0120(10) 0.0099(9) 0.0169(11) C26 0.0399(13) 0.0448(13) 0.0282(11) 0.0085(10) 0.0057(9) 0.0152(10) C27 0.0372(12) 0.0309(11) 0.0288(11) 0.0047(9) 0.0026(9) 0.0111(9) C28 0.0391(12) 0.0305(11) 0.0303(11) 0.0049(9) 0.0015(9) 0.0028(9) O1 0.0636(11) 0.0382(9) 0.0310(8) 0.0109(7) 0.0077(7) 0.0133(8) O2 0.0668(12) 0.0693(12) 0.0355(9) 0.0227(9) 0.0005(8) 0.0231(10) O3 0.0338(9) 0.0501(10) 0.0445(9) 0.0141(8) 0.0063(7) 0.0028(7) O4 0.043(1) 0.0416(9) 0.0451(9) 0.0153(7) 0.0124(7) 0.0017(7) O5 0.0371(9) 0.0285(8) 0.0401(9) 0.0069(6) 0.0103(7) 0.0043(6) C29 0.0457(14) 0.0331(12) 0.0440(13) 0.0085(10) 0.0138(11) 0.0098(10) C30 0.0427(14) 0.0429(13) 0.0461(14) 0.0171(11) 0.0102(11) 0.0100(11) O6 0.0399(9) 0.0565(11) 0.0454(10) 0.0217(8) 0.0139(7) 0.0154(8) C31 0.0505(16) 0.0604(17) 0.0474(14) 0.0213(12) 0.0205(12) 0.0237(13) C32 0.0599(16) 0.0521(15) 0.0391(13) 0.0121(11) 0.0173(12) 0.0216(13) N1 0.0410(12) 0.0465(12) 0.0407(11) 0.0106(9) 0.0112(9) 0.0158(10) C33 0.0396(14) 0.0646(17) 0.0361(13) 0.0078(12) 0.0148(10) 0.0182(13) O7 0.0458(12) 0.0868(16) 0.0871(15) 0.0151(12) 0.0238(11) 0.0278(11) C34 0.0327(12) 0.0415(13) 0.0319(11) 0.0067(10) 0.0067(9) -0.0009(10) C35 0.0340(12) 0.0545(15) 0.0304(12) 0.0012(10) 0.0081(9) 0.0037(11) C36 0.0375(14) 0.0714(19) 0.0420(14) -0.0104(13) 0.0144(11) -0.0011(13) C37 0.0470(16) 0.0633(19) 0.0524(16) -0.0040(14) 0.0193(13) -0.0150(14) C38 0.0561(16) 0.0451(14) 0.0377(13) 0.0032(11) 0.0087(12) -0.0071(12) C39 0.0400(13) 0.0439(13) 0.0245(10) 0.0038(9) 0.0046(9) -0.0027(10) C40 0.0497(14) 0.0384(13) 0.0288(11) 0.0098(9) 0.0016(10) 0.0038(11) O8 0.0634(12) 0.0375(10) 0.0596(11) 0.0147(8) 0.0083(9) 0.0059(8) N2 0.0454(12) 0.0337(11) 0.0388(11) 0.0112(9) 0.0081(9) 0.0096(9) C41 0.0480(15) 0.0461(14) 0.0439(13) 0.0196(11) 0.0108(11) 0.0187(11) C42 0.0695(18) 0.0350(13) 0.0475(14) 0.0166(11) 0.0200(13) 0.0175(12) O9 0.0876(14) 0.0311(9) 0.0352(9) 0.0124(7) 0.0094(9) 0.0029(9) C43 0.124(3) 0.0353(14) 0.0464(16) 0.0097(12) -0.0114(17) 0.0017(16) C44 0.149(3) 0.0315(14) 0.0418(15) 0.0077(12) -0.0010(18) -0.0066(17) O10 0.0506(10) 0.0307(8) 0.0370(8) 0.0121(7) 0.0038(7) 0.0007(7) C45 0.0418(13) 0.0422(13) 0.0350(12) 0.0121(10) 0.0066(10) -0.0044(10) C46 0.0565(17) 0.0695(18) 0.0398(14) 0.0219(13) 0.0099(12) -0.0062(14) C47 0.0662(18) 0.0407(14) 0.0546(16) 0.0136(12) 0.0073(14) -0.0100(13) C48 0.0390(14) 0.074(2) 0.0565(16) 0.0193(15) 0.0098(12) -0.0013(13) C49 0.0321(13) 0.0799(19) 0.0403(13) 0.0210(13) 0.0125(10) 0.0087(13) C50 0.0367(15) 0.105(3) 0.0630(18) 0.0346(18) 0.0049(13) -0.0031(15) C51 0.070(2) 0.115(3) 0.0602(19) 0.0254(19) 0.0374(17) 0.023(2) C52 0.0466(16) 0.078(2) 0.0622(18) 0.0326(16) 0.0052(13) -0.0046(14) N3 0.075(2) 0.093(2) 0.079(2) -0.0072(18) 0.0070(16) 0.0084(17) C53 0.0558(18) 0.0630(19) 0.065(2) 0.0119(16) 0.0133(15) 0.0101(15) C54 0.083(2) 0.092(3) 0.0530(18) 0.0193(18) 0.0021(17) 0.001(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.495(3) yes C1 . C6 . 1.496(3) yes C1 . O1 . 1.217(3) yes C2 . C3 . 1.335(3) yes C2 . C28 . 1.507(3) yes C3 . C4 . 1.467(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.469(3) yes C4 . O2 . 1.228(3) yes C5 . C6 . 1.342(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.501(3) yes C7 . C9 . 1.512(3) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.388(3) yes C8 . C13 . 1.401(3) yes C8 . O5 . 1.391(2) yes C9 . C10 . 1.399(3) yes C10 . C11 . 1.390(3) yes C10 . H101 . 1.000 no C11 . C12 . 1.392(3) yes C11 . C45 . 1.539(3) yes C12 . C13 . 1.389(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.519(3) yes C14 . C16 . 1.507(3) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . C16 . 1.492(3) yes C15 . C20 . 1.490(3) yes C15 . O3 . 1.223(3) yes C16 . C17 . 1.334(3) yes C17 . C18 . 1.464(3) yes C17 . H171 . 1.000 no C18 . C19 . 1.461(3) yes C18 . O4 . 1.239(3) yes C19 . C20 . 1.330(3) yes C19 . H191 . 1.000 no C20 . C21 . 1.507(3) yes C21 . C23 . 1.518(3) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C23 . 1.389(3) yes C22 . C27 . 1.393(3) yes C22 . O10 . 1.388(3) yes C23 . C24 . 1.393(3) yes C24 . C25 . 1.390(3) yes C24 . H241 . 1.000 no C25 . C26 . 1.389(3) yes C25 . C49 . 1.533(3) yes C26 . C27 . 1.386(3) yes C26 . H261 . 1.000 no C27 . C28 . 1.523(3) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no O5 . C29 . 1.442(3) yes C29 . C30 . 1.489(3) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . O6 . 1.418(3) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no O6 . C31 . 1.421(3) yes C31 . C32 . 1.504(4) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . N1 . 1.456(3) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no N1 . C33 . 1.346(3) yes N1 . H1 . 0.92(3) no C33 . O7 . 1.229(3) yes C33 . C35 . 1.502(4) yes C34 . C35 . 1.391(3) yes C34 . C39 . 1.390(3) yes C34 . H341 . 1.000 no C35 . C36 . 1.391(4) yes C36 . C37 . 1.380(4) yes C36 . H361 . 1.000 no C37 . C38 . 1.375(4) yes C37 . H371 . 1.000 no C38 . C39 . 1.396(3) yes C38 . H381 . 1.000 no C39 . C40 . 1.491(3) yes C40 . O8 . 1.235(3) yes C40 . N2 . 1.344(3) yes N2 . C41 . 1.454(3) yes N2 . H2 . 0.86(3) no C41 . C42 . 1.510(3) yes C41 . H411 . 1.000 no C41 . H412 . 1.000 no C42 . O9 . 1.419(3) yes C42 . H421 . 1.000 no C42 . H422 . 1.000 no O9 . C43 . 1.383(3) yes C43 . C44 . 1.392(4) yes C43 . H431 . 1.000 no C43 . H432 . 1.000 no C44 . O10 . 1.443(3) yes C44 . H441 . 1.000 no C44 . H442 . 1.000 no C45 . C46 . 1.528(3) yes C45 . C47 . 1.539(4) yes C45 . C48 . 1.526(4) yes C46 . H461 . 1.000 no C46 . H462 . 1.000 no C46 . H463 . 1.000 no C47 . H471 . 1.000 no C47 . H472 . 1.000 no C47 . H473 . 1.000 no C48 . H481 . 1.000 no C48 . H482 . 1.000 no C48 . H483 . 1.000 no C49 . C50 . 1.526(4) yes C49 . C51 . 1.525(4) yes C49 . C52 . 1.536(4) yes C50 . H501 . 1.000 no C50 . H502 . 1.000 no C50 . H503 . 1.000 no C51 . H511 . 1.000 no C51 . H512 . 1.000 no C51 . H513 . 1.000 no C52 . H521 . 1.000 no C52 . H522 . 1.000 no C52 . H523 . 1.000 no N3 . C53 . 1.133(4) yes C53 . C54 . 1.447(5) yes C54 . H541 . 1.000 no C54 . H542 . 1.000 no C54 . H543 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 119.06(18) yes C2 . C1 . O1 . 120.79(19) yes C6 . C1 . O1 . 120.13(19) yes C1 . C2 . C3 . 119.3(2) yes C1 . C2 . C28 . 115.76(18) yes C3 . C2 . C28 . 124.9(2) yes C2 . C3 . C4 . 121.8(2) yes C2 . C3 . H31 . 119.096 no C4 . C3 . H31 . 119.096 no C3 . C4 . C5 . 118.14(19) yes C3 . C4 . O2 . 121.7(2) yes C5 . C4 . O2 . 120.2(2) yes C4 . C5 . C6 . 122.2(2) yes C4 . C5 . H51 . 118.915 no C6 . C5 . H51 . 118.915 no C1 . C6 . C5 . 118.6(2) yes C1 . C6 . C7 . 117.38(18) yes C5 . C6 . C7 . 123.8(2) yes C6 . C7 . C9 . 114.89(18) yes C6 . C7 . H71 . 108.102 no C9 . C7 . H71 . 108.102 no C6 . C7 . H72 . 108.102 no C9 . C7 . H72 . 108.102 no H71 . C7 . H72 . 109.467 no C9 . C8 . C13 . 120.58(19) yes C9 . C8 . O5 . 120.35(19) yes C13 . C8 . O5 . 119.07(18) yes C7 . C9 . C8 . 120.71(19) yes C7 . C9 . C10 . 120.28(19) yes C8 . C9 . C10 . 118.93(19) yes C9 . C10 . C11 . 122.13(19) yes C9 . C10 . H101 . 118.934 no C11 . C10 . H101 . 118.934 no C10 . C11 . C12 . 116.96(19) yes C10 . C11 . C45 . 122.83(19) yes C12 . C11 . C45 . 120.09(19) yes C11 . C12 . C13 . 122.9(2) yes C11 . C12 . H121 . 118.556 no C13 . C12 . H121 . 118.556 no C8 . C13 . C12 . 118.32(19) yes C8 . C13 . C14 . 120.43(19) yes C12 . C13 . C14 . 121.3(2) yes C13 . C14 . C16 . 112.59(17) yes C13 . C14 . H141 . 108.687 no C16 . C14 . H141 . 108.687 no C13 . C14 . H142 . 108.687 no C16 . C14 . H142 . 108.687 no H141 . C14 . H142 . 109.467 no C16 . C15 . C20 . 118.94(18) yes C16 . C15 . O3 . 120.1(2) yes C20 . C15 . O3 . 121.0(2) yes C14 . C16 . C15 . 117.00(18) yes C14 . C16 . C17 . 123.7(2) yes C15 . C16 . C17 . 119.30(19) yes C16 . C17 . C18 . 121.4(2) yes C16 . C17 . H171 . 119.290 no C18 . C17 . H171 . 119.290 no C17 . C18 . C19 . 118.45(19) yes C17 . C18 . O4 . 121.1(2) yes C19 . C18 . O4 . 120.4(2) yes C18 . C19 . C20 . 122.4(2) yes C18 . C19 . H191 . 118.812 no C20 . C19 . H191 . 118.812 no C15 . C20 . C19 . 118.7(2) yes C15 . C20 . C21 . 118.12(19) yes C19 . C20 . C21 . 123.2(2) yes C20 . C21 . C23 . 111.95(18) yes C20 . C21 . H211 . 108.849 no C23 . C21 . H211 . 108.849 no C20 . C21 . H212 . 108.849 no C23 . C21 . H212 . 108.849 no H211 . C21 . H212 . 109.467 no C23 . C22 . C27 . 121.2(2) yes C23 . C22 . O10 . 118.36(18) yes C27 . C22 . O10 . 120.46(19) yes C21 . C23 . C22 . 120.8(2) yes C21 . C23 . C24 . 120.6(2) yes C22 . C23 . C24 . 118.52(19) yes C23 . C24 . C25 . 122.1(2) yes C23 . C24 . H241 . 118.948 no C25 . C24 . H241 . 118.948 no C24 . C25 . C26 . 117.3(2) yes C24 . C25 . C49 . 123.1(2) yes C26 . C25 . C49 . 119.6(2) yes C25 . C26 . C27 . 122.7(2) yes C25 . C26 . H261 . 118.671 no C27 . C26 . H261 . 118.671 no C22 . C27 . C26 . 118.2(2) yes C22 . C27 . C28 . 122.53(19) yes C26 . C27 . C28 . 118.78(19) yes C2 . C28 . C27 . 107.80(17) yes C2 . C28 . H281 . 109.888 no C27 . C28 . H281 . 109.888 no C2 . C28 . H282 . 109.888 no C27 . C28 . H282 . 109.888 no H281 . C28 . H282 . 109.467 no C8 . O5 . C29 . 111.32(16) yes O5 . C29 . C30 . 110.67(18) yes O5 . C29 . H291 . 109.171 no C30 . C29 . H291 . 109.171 no O5 . C29 . H292 . 109.171 no C30 . C29 . H292 . 109.171 no H291 . C29 . H292 . 109.467 no C29 . C30 . O6 . 110.7(2) yes C29 . C30 . H301 . 109.167 no O6 . C30 . H301 . 109.167 no C29 . C30 . H302 . 109.167 no O6 . C30 . H302 . 109.167 no H301 . C30 . H302 . 109.467 no C30 . O6 . C31 . 111.05(18) yes O6 . C31 . C32 . 109.2(2) yes O6 . C31 . H311 . 109.534 no C32 . C31 . H311 . 109.533 no O6 . C31 . H312 . 109.533 no C32 . C31 . H312 . 109.533 no H311 . C31 . H312 . 109.467 no C31 . C32 . N1 . 113.2(2) yes C31 . C32 . H321 . 108.524 no N1 . C32 . H321 . 108.524 no C31 . C32 . H322 . 108.524 no N1 . C32 . H322 . 108.524 no H321 . C32 . H322 . 109.467 no C32 . N1 . C33 . 120.9(2) yes C32 . N1 . H1 . 115.0(18) no C33 . N1 . H1 . 123.5(18) no N1 . C33 . O7 . 121.6(3) yes N1 . C33 . C35 . 117.6(2) yes O7 . C33 . C35 . 120.7(2) yes C35 . C34 . C39 . 121.0(2) yes C35 . C34 . H341 . 119.487 no C39 . C34 . H341 . 119.487 no C33 . C35 . C34 . 123.7(2) yes C33 . C35 . C36 . 117.7(2) yes C34 . C35 . C36 . 118.4(2) yes C35 . C36 . C37 . 121.1(3) yes C35 . C36 . H361 . 119.439 no C37 . C36 . H361 . 119.439 no C36 . C37 . C38 . 119.9(2) yes C36 . C37 . H371 . 120.038 no C38 . C37 . H371 . 120.038 no C37 . C38 . C39 . 120.4(3) yes C37 . C38 . H381 . 119.794 no C39 . C38 . H381 . 119.794 no C34 . C39 . C38 . 119.0(2) yes C34 . C39 . C40 . 123.4(2) yes C38 . C39 . C40 . 117.6(2) yes C39 . C40 . O8 . 120.3(2) yes C39 . C40 . N2 . 118.5(2) yes O8 . C40 . N2 . 121.2(2) yes C40 . N2 . C41 . 120.5(2) yes C40 . N2 . H2 . 120.7(17) no C41 . N2 . H2 . 118.7(17) no N2 . C41 . C42 . 112.9(2) yes N2 . C41 . H411 . 108.598 no C42 . C41 . H411 . 108.598 no N2 . C41 . H412 . 108.598 no C42 . C41 . H412 . 108.598 no H411 . C41 . H412 . 109.467 no C41 . C42 . O9 . 108.96(19) yes C41 . C42 . H421 . 109.601 no O9 . C42 . H421 . 109.601 no C41 . C42 . H422 . 109.601 no O9 . C42 . H422 . 109.601 no H421 . C42 . H422 . 109.467 no C42 . O9 . C43 . 115.3(2) yes O9 . C43 . C44 . 115.7(3) yes O9 . C43 . H431 . 107.883 no C44 . C43 . H431 . 107.884 no O9 . C43 . H432 . 107.883 no C44 . C43 . H432 . 107.884 no H431 . C43 . H432 . 109.467 no C43 . C44 . O10 . 113.6(3) yes C43 . C44 . H441 . 108.434 no O10 . C44 . H441 . 108.434 no C43 . C44 . H442 . 108.434 no O10 . C44 . H442 . 108.435 no H441 . C44 . H442 . 109.467 no C22 . O10 . C44 . 110.8(2) yes C11 . C45 . C46 . 112.43(19) yes C11 . C45 . C47 . 107.50(19) yes C46 . C45 . C47 . 107.7(2) yes C11 . C45 . C48 . 110.9(2) yes C46 . C45 . C48 . 108.9(2) yes C47 . C45 . C48 . 109.4(2) yes C45 . C46 . H461 . 109.467 no C45 . C46 . H462 . 109.467 no H461 . C46 . H462 . 109.476 no C45 . C46 . H463 . 109.467 no H461 . C46 . H463 . 109.476 no H462 . C46 . H463 . 109.476 no C45 . C47 . H471 . 109.467 no C45 . C47 . H472 . 109.467 no H471 . C47 . H472 . 109.476 no C45 . C47 . H473 . 109.467 no H471 . C47 . H473 . 109.476 no H472 . C47 . H473 . 109.476 no C45 . C48 . H481 . 109.467 no C45 . C48 . H482 . 109.467 no H481 . C48 . H482 . 109.476 no C45 . C48 . H483 . 109.467 no H481 . C48 . H483 . 109.476 no H482 . C48 . H483 . 109.476 no C25 . C49 . C50 . 112.3(2) yes C25 . C49 . C51 . 109.7(2) yes C50 . C49 . C51 . 109.3(2) yes C25 . C49 . C52 . 108.9(2) yes C50 . C49 . C52 . 107.3(2) yes C51 . C49 . C52 . 109.3(2) yes C49 . C50 . H501 . 109.467 no C49 . C50 . H502 . 109.467 no H501 . C50 . H502 . 109.476 no C49 . C50 . H503 . 109.467 no H501 . C50 . H503 . 109.476 no H502 . C50 . H503 . 109.476 no C49 . C51 . H511 . 109.467 no C49 . C51 . H512 . 109.467 no H511 . C51 . H512 . 109.476 no C49 . C51 . H513 . 109.466 no H511 . C51 . H513 . 109.476 no H512 . C51 . H513 . 109.476 no C49 . C52 . H521 . 109.467 no C49 . C52 . H522 . 109.467 no H521 . C52 . H522 . 109.476 no C49 . C52 . H523 . 109.467 no H521 . C52 . H523 . 109.476 no H522 . C52 . H523 . 109.476 no N3 . C53 . C54 . 179.1(4) yes C53 . C54 . H541 . 109.467 no C53 . C54 . H542 . 109.467 no H541 . C54 . H542 . 109.476 no C53 . C54 . H543 . 109.467 no H541 . C54 . H543 . 109.476 no H542 . C54 . H543 . 109.476 no 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_publ_flag N1 H1 O4 0.92(3) 2.28(3) 3.171(3) 164(2) yes N2 H2 O4 0.86(3) 2.38(3) 3.237(3) 175(2) yes