Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'M. Moloney' _publ_contact_author_address ; Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email MARK.MOLONEY@CHEMISTRY.OXFORD.AC.UK _publ_section_title ; 2,5-Disubstituted Pyrrolidines: Synthesis by Enamine Reduction and Subsequent Regioselective and Diastereoselective Alkylations ; loop_ _publ_author_name 'M. Moloney' 'Syed Raziullah Hussaini' data_ac397 _database_code_depnum_ccdc_archive 'CCDC 602416' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # 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 ? _chemical_absolute_configuration syn _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 noref #============================================================= _cell_length_a 8.3002(2) _cell_angle_alpha 90 _cell_length_b 33.6715(4) _cell_angle_beta 90.6345(5) _cell_length_c 10.5310(2) _cell_angle_gamma 90 _cell_volume 2943.03(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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 4 _chemical_formula_sum ' C33 H37 N1 O6 ' _chemical_formula_moiety ' C33 H37 N1 O6 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 543.66 _cell_measurement_reflns_used 17333 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.084 _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 0.99 _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 17333 _reflns_number_total 6438 #6442 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_min 5.207 _diffrn_reflns_theta_max 27.489 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.489 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 43 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.25 _refine_diff_density_max 0.34 _refine_ls_number_reflns 4668 _refine_ls_number_restraints 1 _refine_ls_number_parameters 721 #_refine_ls_R_factor_ref 0.0521 _refine_ls_wR_factor_ref 0.0531 _refine_ls_goodness_of_fit_ref 1.0425 #_reflns_number_all 6438 _refine_ls_R_factor_all 0.0753 _refine_ls_wR_factor_all 0.0561 # 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 4668 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_gt 0.0531 _refine_ls_shift/su_max 0.002088 _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: 1.67 0.134 1.28 ; _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 N1 N 0.1729(4) 0.68445(9) 0.1990(3) 0.0255 1.0000 Uani C1 C 0.3405(4) 0.67161(11) 0.2259(4) 0.0269 1.0000 Uani C2 C 0.3359(5) 0.65873(13) 0.3650(4) 0.0340 1.0000 Uani C3 C 0.1589(5) 0.64863(12) 0.3890(4) 0.0317 1.0000 Uani C4 C 0.0642(4) 0.67806(11) 0.3067(3) 0.0271 1.0000 Uani C5 C 0.1377(5) 0.70475(11) 0.0909(4) 0.0305 1.0000 Uani O1 O 0.2442(4) 0.71442(8) 0.0165(3) 0.0369 1.0000 Uani C6 C -0.0380(5) 0.71280(12) 0.0611(4) 0.0381 1.0000 Uani C7 C 0.3909(4) 0.63917(10) 0.1297(3) 0.0242 1.0000 Uani C8 C 0.5715(4) 0.63321(11) 0.1330(3) 0.0262 1.0000 Uani O2 O 0.6636(3) 0.65019(9) 0.2019(3) 0.0355 1.0000 Uani O3 O 0.6145(3) 0.60705(8) 0.0426(3) 0.0312 1.0000 Uani C9 C 0.7871(5) 0.59868(14) 0.0363(5) 0.0428 1.0000 Uani C10 C 0.8107(6) 0.56814(16) -0.0649(5) 0.0505 1.0000 Uani C11 C 0.2978(4) 0.60053(11) 0.1466(3) 0.0249 1.0000 Uani O4 O 0.1687(4) 0.59413(9) 0.0993(3) 0.0422 1.0000 Uani O5 O 0.3761(3) 0.57559(8) 0.2230(3) 0.0310 1.0000 Uani C12 C 0.2952(5) 0.53785(12) 0.2499(4) 0.0356 1.0000 Uani C13 C 0.4186(6) 0.51031(12) 0.3052(4) 0.0440 1.0000 Uani C14 C 0.0423(5) 0.71775(11) 0.3761(4) 0.0286 1.0000 Uani O6 O -0.0702(3) 0.71072(7) 0.4739(2) 0.0289 1.0000 Uani C15 C -0.1226(4) 0.74539(10) 0.5440(3) 0.0251 1.0000 Uani C16 C -0.2237(4) 0.72798(11) 0.6526(4) 0.0293 1.0000 Uani C17 C -0.2668(5) 0.68847(13) 0.6558(5) 0.0409 1.0000 Uani C18 C -0.3591(6) 0.67416(16) 0.7552(6) 0.0576 1.0000 Uani C19 C -0.4105(5) 0.69840(17) 0.8490(5) 0.0532 1.0000 Uani C20 C -0.3702(5) 0.73844(15) 0.8463(4) 0.0409 1.0000 Uani C21 C -0.2778(5) 0.75295(13) 0.7479(4) 0.0337 1.0000 Uani C22 C 0.0261(4) 0.76704(11) 0.5951(3) 0.0250 1.0000 Uani C23 C 0.1019(5) 0.75388(11) 0.7073(4) 0.0300 1.0000 Uani C24 C 0.2477(5) 0.76976(13) 0.7476(4) 0.0363 1.0000 Uani C25 C 0.3229(5) 0.79891(13) 0.6756(4) 0.0370 1.0000 Uani C26 C 0.2500(5) 0.81227(12) 0.5658(4) 0.0354 1.0000 Uani C27 C 0.1041(5) 0.79641(12) 0.5244(4) 0.0295 1.0000 Uani C28 C -0.2340(5) 0.77090(11) 0.4604(3) 0.0274 1.0000 Uani C29 C -0.2591(5) 0.81132(11) 0.4880(4) 0.0294 1.0000 Uani C30 C -0.3671(5) 0.83348(13) 0.4168(4) 0.0408 1.0000 Uani C31 C -0.4506(6) 0.81706(15) 0.3167(4) 0.0444 1.0000 Uani C32 C -0.4271(6) 0.77717(15) 0.2875(4) 0.0426 1.0000 Uani C33 C -0.3198(5) 0.75451(12) 0.3604(4) 0.0345 1.0000 Uani N2 N 0.4040(3) 0.47196(9) -0.2955(3) 0.0233 1.0000 Uani C34 C 0.2374(4) 0.48476(10) -0.2711(3) 0.0247 1.0000 Uani C35 C 0.2434(5) 0.49847(12) -0.1318(3) 0.0319 1.0000 Uani C36 C 0.4196(5) 0.50923(11) -0.1069(3) 0.0308 1.0000 Uani C37 C 0.5115(4) 0.47892(10) -0.1860(3) 0.0250 1.0000 Uani C38 C 0.4364(4) 0.44969(10) -0.3997(3) 0.0258 1.0000 Uani O7 O 0.3286(3) 0.43994(8) -0.4731(3) 0.0344 1.0000 Uani C39 C 0.6096(5) 0.43889(12) -0.4252(4) 0.0349 1.0000 Uani C40 C 0.1832(4) 0.51619(10) -0.3688(3) 0.0245 1.0000 Uani C41 C 0.0028(5) 0.52179(10) -0.3674(4) 0.0268 1.0000 Uani O8 O -0.0879(3) 0.50504(9) -0.2956(3) 0.0345 1.0000 Uani O9 O -0.0444(3) 0.54682(8) -0.4586(3) 0.0314 1.0000 Uani C42 C -0.2175(5) 0.55488(14) -0.4663(5) 0.0413 1.0000 Uani C43 C -0.2436(6) 0.58434(17) -0.5712(5) 0.0553 1.0000 Uani C44 C 0.2738(4) 0.55551(10) -0.3543(4) 0.0271 1.0000 Uani O10 O 0.4011(3) 0.56247(9) -0.3986(3) 0.0423 1.0000 Uani O11 O 0.1923(3) 0.58018(8) -0.2774(3) 0.0307 1.0000 Uani C45 C 0.2681(5) 0.61842(12) -0.2509(4) 0.0364 1.0000 Uani C46 C 0.1410(6) 0.64537(13) -0.2002(5) 0.0472 1.0000 Uani C47 C 0.5330(5) 0.43962(11) -0.1142(4) 0.0288 1.0000 Uani O12 O 0.6451(3) 0.44595(7) -0.0136(2) 0.0267 1.0000 Uani C48 C 0.6956(4) 0.41035(10) 0.0533(3) 0.0252 1.0000 Uani C49 C 0.7982(4) 0.42543(11) 0.1654(3) 0.0248 1.0000 Uani C50 C 0.8411(5) 0.46482(12) 0.1787(4) 0.0369 1.0000 Uani C51 C 0.9319(6) 0.47674(14) 0.2848(5) 0.0470 1.0000 Uani C52 C 0.9803(5) 0.44994(15) 0.3759(4) 0.0425 1.0000 Uani C53 C 0.9368(5) 0.41027(14) 0.3631(4) 0.0370 1.0000 Uani C54 C 0.8471(5) 0.39820(11) 0.2586(4) 0.0301 1.0000 Uani C55 C 0.5433(4) 0.38912(10) 0.0993(3) 0.0250 1.0000 Uani C56 C 0.4681(5) 0.40207(11) 0.2085(4) 0.0294 1.0000 Uani C57 C 0.3180(5) 0.38756(13) 0.2442(4) 0.0360 1.0000 Uani C58 C 0.2424(5) 0.35933(13) 0.1701(4) 0.0374 1.0000 Uani C59 C 0.3162(5) 0.34560(12) 0.0611(4) 0.0370 1.0000 Uani C60 C 0.4655(5) 0.36018(12) 0.0262(3) 0.0293 1.0000 Uani C61 C 0.8036(5) 0.38530(11) -0.0330(3) 0.0267 1.0000 Uani C62 C 0.8235(5) 0.34472(12) -0.0130(4) 0.0331 1.0000 Uani C63 C 0.9262(6) 0.32273(13) -0.0907(4) 0.0419 1.0000 Uani C64 C 1.0093(5) 0.34078(15) -0.1870(4) 0.0437 1.0000 Uani C65 C 0.9928(5) 0.38106(14) -0.2067(4) 0.0402 1.0000 Uani C66 C 0.8912(5) 0.40352(12) -0.1300(4) 0.0321 1.0000 Uani H11 H 0.4250 0.6925 0.2150 0.0323 1.0000 Uiso H21 H 0.3726 0.6808 0.4218 0.0408 1.0000 Uiso H22 H 0.4057 0.6349 0.3794 0.0408 1.0000 Uiso H31 H 0.1325 0.6522 0.4807 0.0381 1.0000 Uiso H32 H 0.1347 0.6207 0.3628 0.0381 1.0000 Uiso H41 H -0.0458 0.6682 0.2832 0.0326 1.0000 Uiso H61 H -0.1057 0.7029 0.1323 0.0457 1.0000 Uiso H62 H -0.0548 0.7420 0.0505 0.0457 1.0000 Uiso H63 H -0.0694 0.6988 -0.0192 0.0457 1.0000 Uiso H71 H 0.3610 0.6488 0.0427 0.0290 1.0000 Uiso H91 H 0.8472 0.6235 0.0145 0.0515 1.0000 Uiso H92 H 0.8268 0.5883 0.1198 0.0515 1.0000 Uiso H101 H 0.9280 0.5618 -0.0716 0.0607 1.0000 Uiso H102 H 0.7701 0.5787 -0.1480 0.0607 1.0000 Uiso H103 H 0.7498 0.5435 -0.0427 0.0607 1.0000 Uiso H121 H 0.2066 0.5422 0.3120 0.0427 1.0000 Uiso H122 H 0.2494 0.5264 0.1697 0.0427 1.0000 Uiso H131 H 0.3672 0.4842 0.3247 0.0529 1.0000 Uiso H132 H 0.4642 0.5221 0.3850 0.0529 1.0000 Uiso H133 H 0.5070 0.5063 0.2427 0.0529 1.0000 Uiso H141 H 0.0000 0.7384 0.3161 0.0344 1.0000 Uiso H142 H 0.1474 0.7269 0.4132 0.0344 1.0000 Uiso H171 H -0.2317 0.6701 0.5868 0.0492 1.0000 Uiso H181 H -0.3881 0.6454 0.7574 0.0694 1.0000 Uiso H191 H -0.4769 0.6876 0.9197 0.0640 1.0000 Uiso H201 H -0.4077 0.7567 0.9149 0.0492 1.0000 Uiso H211 H -0.2496 0.7818 0.7456 0.0405 1.0000 Uiso H231 H 0.0496 0.7327 0.7590 0.0361 1.0000 Uiso H241 H 0.2990 0.7603 0.8285 0.0436 1.0000 Uiso H251 H 0.4292 0.8101 0.7035 0.0444 1.0000 Uiso H261 H 0.3026 0.8337 0.5151 0.0425 1.0000 Uiso H271 H 0.0543 0.8061 0.4432 0.0355 1.0000 Uiso H291 H -0.1982 0.8241 0.5596 0.0354 1.0000 Uiso H301 H -0.3848 0.8620 0.4386 0.0490 1.0000 Uiso H311 H -0.5274 0.8335 0.2653 0.0534 1.0000 Uiso H321 H -0.4869 0.7648 0.2147 0.0510 1.0000 Uiso H331 H -0.3047 0.7258 0.3396 0.0414 1.0000 Uiso H341 H 0.1537 0.4636 -0.2820 0.0297 1.0000 Uiso H351 H 0.1725 0.5221 -0.1193 0.0383 1.0000 Uiso H352 H 0.2087 0.4766 -0.0741 0.0383 1.0000 Uiso H361 H 0.4430 0.5369 -0.1356 0.0370 1.0000 Uiso H362 H 0.4476 0.5066 -0.0147 0.0370 1.0000 Uiso H371 H 0.6215 0.4886 -0.2083 0.0300 1.0000 Uiso H391 H 0.6800 0.4493 -0.3552 0.0419 1.0000 Uiso H392 H 0.6433 0.4508 -0.5077 0.0419 1.0000 Uiso H393 H 0.6204 0.4093 -0.4297 0.0419 1.0000 Uiso H401 H 0.2123 0.5058 -0.4544 0.0293 1.0000 Uiso H421 H -0.2556 0.5662 -0.3841 0.0495 1.0000 Uiso H422 H -0.2776 0.5298 -0.4854 0.0495 1.0000 Uiso H431 H -0.3611 0.5906 -0.5792 0.0662 1.0000 Uiso H432 H -0.1826 0.6092 -0.5516 0.0662 1.0000 Uiso H433 H -0.2046 0.5729 -0.6529 0.0662 1.0000 Uiso H451 H 0.3134 0.6298 -0.3307 0.0436 1.0000 Uiso H452 H 0.3565 0.6151 -0.1865 0.0436 1.0000 Uiso H461 H 0.1892 0.6719 -0.1810 0.0565 1.0000 Uiso H462 H 0.0528 0.6484 -0.2650 0.0565 1.0000 Uiso H463 H 0.0959 0.6337 -0.1208 0.0565 1.0000 Uiso H471 H 0.5746 0.4188 -0.1730 0.0344 1.0000 Uiso H472 H 0.4273 0.4309 -0.0790 0.0344 1.0000 Uiso H501 H 0.8075 0.4847 0.1130 0.0442 1.0000 Uiso H511 H 0.9622 0.5053 0.2945 0.0564 1.0000 Uiso H521 H 1.0462 0.4589 0.4507 0.0510 1.0000 Uiso H531 H 0.9702 0.3905 0.4292 0.0444 1.0000 Uiso H541 H 0.8168 0.3696 0.2494 0.0361 1.0000 Uiso H561 H 0.5230 0.4224 0.2631 0.0353 1.0000 Uiso H571 H 0.2657 0.3976 0.3231 0.0433 1.0000 Uiso H581 H 0.1346 0.3488 0.1948 0.0449 1.0000 Uiso H591 H 0.2614 0.3251 0.0074 0.0443 1.0000 Uiso H601 H 0.5181 0.3499 -0.0522 0.0351 1.0000 Uiso H621 H 0.7642 0.3312 0.0570 0.0398 1.0000 Uiso H631 H 0.9394 0.2936 -0.0759 0.0503 1.0000 Uiso H641 H 1.0814 0.3248 -0.2426 0.0524 1.0000 Uiso H651 H 1.0539 0.3943 -0.2763 0.0483 1.0000 Uiso H661 H 0.8809 0.4328 -0.1443 0.0386 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 N1 0.0304(16) 0.0231(15) 0.0231(14) -0.0024(12) 0.0012(13) 0.0064(12) C1 0.0216(18) 0.0274(18) 0.0319(19) -0.0026(15) 0.0019(15) 0.0033(14) C2 0.033(2) 0.040(2) 0.0288(19) -0.0004(17) -0.0027(16) 0.0084(17) C3 0.039(2) 0.030(2) 0.0264(18) 0.0008(15) 0.0081(17) 0.0098(16) C4 0.0271(18) 0.0235(17) 0.0309(18) 0.0004(15) 0.0038(15) 0.0029(15) C5 0.041(2) 0.0170(17) 0.0338(19) -0.0019(14) 0.0020(17) 0.0045(15) O1 0.0488(17) 0.0289(14) 0.0330(14) 0.0076(12) 0.0111(13) 0.0021(12) C6 0.040(2) 0.029(2) 0.045(2) -0.0008(18) -0.0076(19) 0.0054(17) C7 0.0294(19) 0.0179(16) 0.0253(17) 0.0028(13) 0.0024(14) -0.0008(13) C8 0.0295(19) 0.0218(17) 0.0274(18) 0.0006(14) 0.0065(16) -0.0008(14) O2 0.0276(14) 0.0389(16) 0.0401(15) -0.0099(13) -0.0007(12) -0.0014(12) O3 0.0284(14) 0.0302(14) 0.0350(14) -0.0067(11) 0.0043(11) 0.0015(11) C9 0.026(2) 0.043(2) 0.060(3) -0.011(2) 0.0118(19) 0.0025(18) C10 0.038(2) 0.051(3) 0.063(3) -0.017(2) 0.012(2) 0.010(2) C11 0.0226(19) 0.0244(18) 0.0277(18) 0.0021(14) 0.0030(15) 0.0031(14) O4 0.0282(16) 0.0354(17) 0.063(2) 0.0088(14) -0.0096(14) -0.0050(12) O5 0.0280(14) 0.0239(13) 0.0410(15) 0.0067(11) -0.0005(11) -0.0033(11) C12 0.046(2) 0.0209(18) 0.040(2) 0.0039(16) 0.0051(18) -0.0065(16) C13 0.061(3) 0.023(2) 0.048(3) 0.0079(18) 0.006(2) 0.0021(19) C14 0.0313(19) 0.0255(18) 0.0292(18) -0.0002(15) 0.0080(15) 0.0009(15) O6 0.0307(14) 0.0208(12) 0.0353(14) -0.0021(11) 0.0097(11) 0.0034(10) C15 0.030(2) 0.0198(16) 0.0253(17) 0.0004(13) 0.0076(15) 0.0036(14) C16 0.0239(18) 0.0279(19) 0.036(2) 0.0090(16) 0.0050(16) 0.0021(14) C17 0.034(2) 0.031(2) 0.058(3) 0.0095(19) 0.014(2) 0.0006(17) C18 0.045(3) 0.042(3) 0.087(4) 0.024(3) 0.023(3) -0.008(2) C19 0.032(2) 0.070(3) 0.058(3) 0.035(3) 0.016(2) 0.007(2) C20 0.028(2) 0.059(3) 0.036(2) 0.014(2) 0.0104(17) 0.0113(19) C21 0.031(2) 0.038(2) 0.032(2) 0.0078(17) 0.0082(16) 0.0070(17) C22 0.0267(18) 0.0216(17) 0.0269(17) 0.0003(14) 0.0092(15) 0.0024(14) C23 0.035(2) 0.0256(18) 0.0295(19) 0.0043(15) 0.0045(16) 0.0064(15) C24 0.035(2) 0.037(2) 0.036(2) 0.0041(18) 0.0000(18) 0.0034(18) C25 0.033(2) 0.034(2) 0.045(2) -0.0008(18) 0.0011(18) -0.0025(17) C26 0.035(2) 0.030(2) 0.042(2) 0.0021(17) 0.0090(18) -0.0059(16) C27 0.0297(19) 0.0280(19) 0.0309(19) 0.0018(15) 0.0043(16) -0.0007(15) C28 0.030(2) 0.0285(19) 0.0242(17) 0.0046(15) 0.0106(15) 0.0014(15) C29 0.032(2) 0.0272(19) 0.0290(19) 0.0050(15) 0.0070(16) 0.0042(15) C30 0.045(3) 0.037(2) 0.040(2) 0.0127(19) 0.016(2) 0.0083(19) C31 0.044(3) 0.052(3) 0.037(2) 0.018(2) 0.009(2) 0.015(2) C32 0.038(2) 0.055(3) 0.035(2) 0.007(2) -0.0055(18) -0.001(2) C33 0.038(2) 0.034(2) 0.031(2) 0.0014(17) 0.0001(17) 0.0039(17) N2 0.0243(15) 0.0220(14) 0.0235(14) -0.0009(11) -0.0009(12) 0.0031(12) C34 0.0256(19) 0.0223(17) 0.0263(18) 0.0045(14) 0.0023(14) 0.0027(13) C35 0.037(2) 0.035(2) 0.0235(17) 0.0032(16) 0.0017(15) 0.0103(17) C36 0.040(2) 0.0292(19) 0.0235(17) -0.0031(15) 0.0015(16) 0.0096(16) C37 0.0291(19) 0.0200(16) 0.0260(17) -0.0017(14) -0.0024(14) 0.0033(14) C38 0.0296(19) 0.0189(16) 0.0290(18) 0.0012(14) -0.0013(15) 0.0023(14) O7 0.0387(16) 0.0251(14) 0.0392(15) -0.0053(12) -0.0087(13) 0.0062(11) C39 0.037(2) 0.030(2) 0.037(2) -0.0048(16) 0.0063(17) 0.0021(17) C40 0.0259(18) 0.0214(17) 0.0260(17) -0.0014(14) -0.0018(14) 0.0018(14) C41 0.0307(19) 0.0210(17) 0.0286(18) -0.0047(14) -0.0053(16) -0.0017(14) O8 0.0232(13) 0.0386(15) 0.0417(15) 0.0078(13) 0.0034(12) -0.0019(11) O9 0.0253(13) 0.0325(14) 0.0363(14) 0.0062(11) -0.0026(11) 0.0040(11) C42 0.024(2) 0.046(3) 0.054(3) 0.011(2) -0.0089(18) 0.0028(18) C43 0.040(3) 0.054(3) 0.071(3) 0.014(3) -0.013(2) 0.013(2) C44 0.0254(19) 0.0196(17) 0.036(2) -0.0020(15) -0.0011(16) 0.0048(14) O10 0.0319(15) 0.0378(16) 0.0575(19) 0.0024(14) 0.0114(14) -0.0045(12) O11 0.0292(14) 0.0240(13) 0.0388(15) -0.0057(11) 0.0007(11) -0.0013(11) C45 0.045(2) 0.0222(19) 0.042(2) -0.0050(16) -0.0088(19) -0.0036(17) C46 0.063(3) 0.025(2) 0.053(3) -0.0116(19) -0.010(2) 0.008(2) C47 0.0282(19) 0.0227(17) 0.035(2) 0.0029(15) -0.0066(15) 0.0012(14) O12 0.0271(13) 0.0226(12) 0.0301(13) 0.0020(10) -0.0100(10) 0.0013(10) C48 0.0267(18) 0.0212(17) 0.0278(18) 0.0028(14) -0.0045(14) 0.0016(14) C49 0.0216(17) 0.0247(17) 0.0281(18) -0.0038(14) 0.0015(14) 0.0034(14) C50 0.032(2) 0.031(2) 0.047(2) -0.0009(18) -0.0088(18) -0.0040(17) C51 0.040(2) 0.040(2) 0.061(3) -0.022(2) -0.007(2) -0.001(2) C52 0.027(2) 0.061(3) 0.040(2) -0.023(2) -0.0091(17) 0.000(2) C53 0.032(2) 0.053(3) 0.0262(19) -0.0075(18) -0.0061(16) 0.0124(18) C54 0.032(2) 0.0303(19) 0.0277(18) -0.0050(15) -0.0018(15) 0.0040(16) C55 0.0304(19) 0.0194(16) 0.0251(17) 0.0027(14) -0.0048(14) 0.0002(14) C56 0.028(2) 0.0226(18) 0.037(2) -0.0025(15) -0.0017(16) 0.0043(14) C57 0.030(2) 0.038(2) 0.040(2) -0.0035(18) 0.0036(17) 0.0030(17) C58 0.0234(19) 0.038(2) 0.051(3) 0.0073(19) -0.0006(18) -0.0036(17) C59 0.042(2) 0.031(2) 0.038(2) -0.0029(17) -0.0076(18) -0.0054(18) C60 0.034(2) 0.0295(19) 0.0243(18) -0.0003(15) -0.0047(15) -0.0041(16) C61 0.031(2) 0.0235(17) 0.0254(17) -0.0029(14) -0.0048(15) 0.0025(14) C62 0.039(2) 0.0275(19) 0.033(2) -0.0063(16) -0.0005(17) 0.0016(16) C63 0.052(3) 0.033(2) 0.041(2) -0.0110(18) 0.000(2) 0.0121(19) C64 0.038(2) 0.051(3) 0.042(2) -0.018(2) -0.0018(19) 0.013(2) C65 0.038(2) 0.051(3) 0.031(2) -0.0031(18) 0.0022(18) -0.001(2) C66 0.033(2) 0.031(2) 0.0325(19) -0.0011(16) 0.0020(16) 0.0008(16) _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 N1 . C1 . 1.481(5) yes N1 . C4 . 1.473(5) yes N1 . C5 . 1.357(5) yes C1 . C2 . 1.529(5) yes C1 . C7 . 1.550(5) yes C1 . H11 . 1.000 no C2 . C3 . 1.532(6) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.528(5) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C14 . 1.535(5) yes C4 . H41 . 1.000 no C5 . O1 . 1.231(5) yes C5 . C6 . 1.513(6) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . C8 . 1.513(5) yes C7 . C11 . 1.525(5) yes C7 . H71 . 1.000 no C8 . O2 . 1.194(5) yes C8 . O3 . 1.347(4) yes O3 . C9 . 1.462(5) yes C9 . C10 . 1.495(7) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . O4 . 1.196(5) yes C11 . O5 . 1.328(4) yes O5 . C12 . 1.466(4) yes C12 . C13 . 1.495(6) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . O6 . 1.418(4) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no O6 . C15 . 1.450(4) yes C15 . C16 . 1.542(5) yes C15 . C22 . 1.526(5) yes C15 . C28 . 1.533(5) yes C16 . C17 . 1.378(6) yes C16 . C21 . 1.388(6) yes C17 . C18 . 1.389(6) yes C17 . H171 . 1.000 no C18 . C19 . 1.354(8) yes C18 . H181 . 1.000 no C19 . C20 . 1.390(8) yes C19 . H191 . 1.000 no C20 . C21 . 1.385(6) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no C22 . C23 . 1.404(5) yes C22 . C27 . 1.401(5) yes C23 . C24 . 1.386(6) yes C23 . H231 . 1.000 no C24 . C25 . 1.392(6) yes C24 . H241 . 1.000 no C25 . C26 . 1.375(6) yes C25 . H251 . 1.000 no C26 . C27 . 1.389(6) yes C26 . H261 . 1.000 no C27 . H271 . 1.000 no C28 . C29 . 1.408(5) yes C28 . C33 . 1.380(6) yes C29 . C30 . 1.382(6) yes C29 . H291 . 1.000 no C30 . C31 . 1.371(7) yes C30 . H301 . 1.000 no C31 . C32 . 1.392(7) yes C31 . H311 . 1.000 no C32 . C33 . 1.396(6) yes C32 . H321 . 1.000 no C33 . H331 . 1.000 no N2 . C34 . 1.474(5) yes N2 . C37 . 1.468(5) yes N2 . C38 . 1.359(5) yes C34 . C35 . 1.538(5) yes C34 . C40 . 1.539(5) yes C34 . H341 . 1.000 no C35 . C36 . 1.527(6) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no C36 . C37 . 1.527(5) yes C36 . H361 . 1.000 no C36 . H362 . 1.000 no C37 . C47 . 1.534(5) yes C37 . H371 . 1.000 no C38 . O7 . 1.221(5) yes C38 . C39 . 1.510(5) yes C39 . H391 . 1.000 no C39 . H392 . 1.000 no C39 . H393 . 1.000 no C40 . C41 . 1.509(5) yes C40 . C44 . 1.529(5) yes C40 . H401 . 1.000 no C41 . O8 . 1.212(5) yes C41 . O9 . 1.334(5) yes O9 . C42 . 1.464(5) yes C42 . C43 . 1.499(7) yes C42 . H421 . 1.000 no C42 . H422 . 1.000 no C43 . H431 . 1.000 no C43 . H432 . 1.000 no C43 . H433 . 1.000 no C44 . O10 . 1.183(5) yes C44 . O11 . 1.347(4) yes O11 . C45 . 1.459(5) yes C45 . C46 . 1.495(6) yes C45 . H451 . 1.000 no C45 . H452 . 1.000 no C46 . H461 . 1.000 no C46 . H462 . 1.000 no C46 . H463 . 1.000 no C47 . O12 . 1.418(4) yes C47 . H471 . 1.000 no C47 . H472 . 1.000 no O12 . C48 . 1.450(4) yes C48 . C49 . 1.534(5) yes C48 . C55 . 1.536(5) yes C48 . C61 . 1.536(5) yes C49 . C50 . 1.380(5) yes C49 . C54 . 1.400(5) yes C50 . C51 . 1.400(6) yes C50 . H501 . 1.000 no C51 . C52 . 1.374(7) yes C51 . H511 . 1.000 no C52 . C53 . 1.390(7) yes C52 . H521 . 1.000 no C53 . C54 . 1.383(6) yes C53 . H531 . 1.000 no C54 . H541 . 1.000 no C55 . C56 . 1.384(5) yes C55 . C60 . 1.396(5) yes C56 . C57 . 1.394(6) yes C56 . H561 . 1.000 no C57 . C58 . 1.377(6) yes C57 . H571 . 1.000 no C58 . C59 . 1.386(6) yes C58 . H581 . 1.000 no C59 . C60 . 1.387(6) yes C59 . H591 . 1.000 no C60 . H601 . 1.000 no C61 . C62 . 1.392(5) yes C61 . C66 . 1.402(6) yes C62 . C63 . 1.400(6) yes C62 . H621 . 1.000 no C63 . C64 . 1.374(7) yes C63 . H631 . 1.000 no C64 . C65 . 1.379(7) yes C64 . H641 . 1.000 no C65 . C66 . 1.397(6) yes C65 . H651 . 1.000 no C66 . H661 . 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 C1 . N1 . C4 . 113.1(3) yes C1 . N1 . C5 . 120.1(3) yes C4 . N1 . C5 . 126.3(3) yes N1 . C1 . C2 . 103.5(3) yes N1 . C1 . C7 . 109.9(3) yes C2 . C1 . C7 . 115.9(3) yes N1 . C1 . H11 . 115.530 no C2 . C1 . H11 . 109.525 no C7 . C1 . H11 . 103.051 no C1 . C2 . C3 . 104.8(3) yes C1 . C2 . H21 . 110.627 no C3 . C2 . H21 . 110.627 no C1 . C2 . H22 . 110.627 no C3 . C2 . H22 . 110.627 no H21 . C2 . H22 . 109.466 no C2 . C3 . C4 . 104.5(3) yes C2 . C3 . H31 . 110.696 no C4 . C3 . H31 . 110.696 no C2 . C3 . H32 . 110.696 no C4 . C3 . H32 . 110.696 no H31 . C3 . H32 . 109.467 no N1 . C4 . C3 . 102.5(3) yes N1 . C4 . C14 . 108.4(3) yes C3 . C4 . C14 . 110.9(3) yes N1 . C4 . H41 . 115.057 no C3 . C4 . H41 . 112.725 no C14 . C4 . H41 . 107.183 no N1 . C5 . O1 . 121.2(4) yes N1 . C5 . C6 . 117.6(4) yes O1 . C5 . C6 . 121.2(4) yes C5 . C6 . H61 . 109.467 no C5 . C6 . H62 . 109.467 no H61 . C6 . H62 . 109.476 no C5 . C6 . H63 . 109.467 no H61 . C6 . H63 . 109.475 no H62 . C6 . H63 . 109.476 no C1 . C7 . C8 . 110.7(3) yes C1 . C7 . C11 . 112.6(3) yes C8 . C7 . C11 . 112.8(3) yes C1 . C7 . H71 . 107.673 no C8 . C7 . H71 . 107.422 no C11 . C7 . H71 . 105.272 no C7 . C8 . O2 . 125.3(3) yes C7 . C8 . O3 . 109.9(3) yes O2 . C8 . O3 . 124.8(3) yes C8 . O3 . C9 . 115.2(3) yes O3 . C9 . C10 . 107.5(4) yes O3 . C9 . H91 . 109.953 no C10 . C9 . H91 . 109.953 no O3 . C9 . H92 . 109.953 no C10 . C9 . H92 . 109.953 no H91 . C9 . H92 . 109.467 no C9 . C10 . H101 . 109.467 no C9 . C10 . H102 . 109.466 no H101 . C10 . H102 . 109.476 no C9 . C10 . H103 . 109.467 no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no C7 . C11 . O4 . 123.9(3) yes C7 . C11 . O5 . 111.4(3) yes O4 . C11 . O5 . 124.6(3) yes C11 . O5 . C12 . 116.3(3) yes O5 . C12 . C13 . 107.4(3) yes O5 . C12 . H121 . 109.979 no C13 . C12 . H121 . 109.979 no O5 . C12 . H122 . 109.979 no C13 . C12 . H122 . 109.979 no H121 . C12 . H122 . 109.467 no C12 . C13 . H131 . 109.466 no C12 . C13 . H132 . 109.466 no H131 . C13 . H132 . 109.476 no C12 . C13 . H133 . 109.467 no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C4 . C14 . O6 . 106.4(3) yes C4 . C14 . H141 . 110.227 no O6 . C14 . H141 . 110.227 no C4 . C14 . H142 . 110.227 no O6 . C14 . H142 . 110.227 no H141 . C14 . H142 . 109.467 no C14 . O6 . C15 . 116.0(3) yes O6 . C15 . C16 . 103.9(3) yes O6 . C15 . C22 . 108.5(3) yes C16 . C15 . C22 . 111.4(3) yes O6 . C15 . C28 . 110.0(3) yes C16 . C15 . C28 . 108.0(3) yes C22 . C15 . C28 . 114.5(3) yes C15 . C16 . C17 . 121.9(4) yes C15 . C16 . C21 . 119.3(3) yes C17 . C16 . C21 . 118.7(4) yes C16 . C17 . C18 . 119.9(4) yes C16 . C17 . H171 . 120.036 no C18 . C17 . H171 . 120.036 no C17 . C18 . C19 . 121.4(5) yes C17 . C18 . H181 . 119.299 no C19 . C18 . H181 . 119.299 no C18 . C19 . C20 . 119.5(4) yes C18 . C19 . H191 . 120.261 no C20 . C19 . H191 . 120.261 no C19 . C20 . C21 . 119.5(4) yes C19 . C20 . H201 . 120.231 no C21 . C20 . H201 . 120.231 no C16 . C21 . C20 . 120.9(4) yes C16 . C21 . H211 . 119.550 no C20 . C21 . H211 . 119.550 no C15 . C22 . C23 . 119.9(3) yes C15 . C22 . C27 . 121.8(3) yes C23 . C22 . C27 . 117.7(4) yes C22 . C23 . C24 . 121.2(4) yes C22 . C23 . H231 . 119.407 no C24 . C23 . H231 . 119.407 no C23 . C24 . C25 . 120.0(4) yes C23 . C24 . H241 . 119.988 no C25 . C24 . H241 . 119.988 no C24 . C25 . C26 . 119.5(4) yes C24 . C25 . H251 . 120.229 no C26 . C25 . H251 . 120.229 no C25 . C26 . C27 . 120.8(4) yes C25 . C26 . H261 . 119.604 no C27 . C26 . H261 . 119.604 no C22 . C27 . C26 . 120.8(4) yes C22 . C27 . H271 . 119.617 no C26 . C27 . H271 . 119.617 no C15 . C28 . C29 . 120.8(3) yes C15 . C28 . C33 . 121.1(3) yes C29 . C28 . C33 . 117.9(4) yes C28 . C29 . C30 . 120.4(4) yes C28 . C29 . H291 . 119.785 no C30 . C29 . H291 . 119.785 no C29 . C30 . C31 . 121.3(4) yes C29 . C30 . H301 . 119.375 no C31 . C30 . H301 . 119.375 no C30 . C31 . C32 . 119.2(4) yes C30 . C31 . H311 . 120.396 no C32 . C31 . H311 . 120.396 no C31 . C32 . C33 . 119.7(4) yes C31 . C32 . H321 . 120.133 no C33 . C32 . H321 . 120.133 no C28 . C33 . C32 . 121.4(4) yes C28 . C33 . H331 . 119.281 no C32 . C33 . H331 . 119.281 no C34 . N2 . C37 . 112.3(3) yes C34 . N2 . C38 . 119.7(3) yes C37 . N2 . C38 . 126.8(3) yes N2 . C34 . C35 . 103.5(3) yes N2 . C34 . C40 . 110.7(3) yes C35 . C34 . C40 . 115.9(3) yes N2 . C34 . H341 . 115.070 no C35 . C34 . H341 . 109.756 no C40 . C34 . H341 . 102.432 no C34 . C35 . C36 . 104.8(3) yes C34 . C35 . H351 . 110.619 no C36 . C35 . H351 . 110.619 no C34 . C35 . H352 . 110.619 no C36 . C35 . H352 . 110.619 no H351 . C35 . H352 . 109.466 no C35 . C36 . C37 . 103.3(3) yes C35 . C36 . H361 . 110.981 no C37 . C36 . H361 . 110.981 no C35 . C36 . H362 . 110.981 no C37 . C36 . H362 . 110.980 no H361 . C36 . H362 . 109.466 no N2 . C37 . C36 . 103.4(3) yes N2 . C37 . C47 . 108.4(3) yes C36 . C37 . C47 . 111.3(3) yes N2 . C37 . H371 . 114.621 no C36 . C37 . H371 . 111.873 no C47 . C37 . H371 . 107.212 no N2 . C38 . O7 . 120.7(3) yes N2 . C38 . C39 . 118.3(3) yes O7 . C38 . C39 . 121.0(3) yes C38 . C39 . H391 . 109.466 no C38 . C39 . H392 . 109.467 no H391 . C39 . H392 . 109.476 no C38 . C39 . H393 . 109.467 no H391 . C39 . H393 . 109.476 no H392 . C39 . H393 . 109.476 no C34 . C40 . C41 . 111.2(3) yes C34 . C40 . C44 . 112.9(3) yes C41 . C40 . C44 . 112.2(3) yes C34 . C40 . H401 . 106.801 no C41 . C40 . H401 . 107.560 no C44 . C40 . H401 . 105.708 no C40 . C41 . O8 . 124.8(3) yes C40 . C41 . O9 . 110.8(3) yes O8 . C41 . O9 . 124.3(3) yes C41 . O9 . C42 . 115.9(3) yes O9 . C42 . C43 . 107.3(4) yes O9 . C42 . H421 . 110.012 no C43 . C42 . H421 . 110.013 no O9 . C42 . H422 . 110.012 no C43 . C42 . H422 . 110.013 no H421 . C42 . H422 . 109.466 no C42 . C43 . H431 . 109.466 no C42 . C43 . H432 . 109.466 no H431 . C43 . H432 . 109.476 no C42 . C43 . H433 . 109.467 no H431 . C43 . H433 . 109.476 no H432 . C43 . H433 . 109.476 no C40 . C44 . O10 . 124.9(3) yes C40 . C44 . O11 . 110.1(3) yes O10 . C44 . O11 . 124.8(3) yes C44 . O11 . C45 . 116.2(3) yes O11 . C45 . C46 . 107.4(4) yes O11 . C45 . H451 . 109.982 no C46 . C45 . H451 . 109.982 no O11 . C45 . H452 . 109.982 no C46 . C45 . H452 . 109.982 no H451 . C45 . H452 . 109.466 no C45 . C46 . H461 . 109.467 no C45 . C46 . H462 . 109.467 no H461 . C46 . H462 . 109.475 no C45 . C46 . H463 . 109.467 no H461 . C46 . H463 . 109.476 no H462 . C46 . H463 . 109.476 no C37 . C47 . O12 . 108.1(3) yes C37 . C47 . H471 . 109.821 no O12 . C47 . H471 . 109.821 no C37 . C47 . H472 . 109.821 no O12 . C47 . H472 . 109.821 no H471 . C47 . H472 . 109.467 no C47 . O12 . C48 . 115.0(3) yes O12 . C48 . C49 . 104.8(3) yes O12 . C48 . C55 . 107.7(3) yes C49 . C48 . C55 . 111.3(3) yes O12 . C48 . C61 . 109.5(3) yes C49 . C48 . C61 . 108.3(3) yes C55 . C48 . C61 . 114.8(3) yes C48 . C49 . C50 . 122.4(3) yes C48 . C49 . C54 . 118.5(3) yes C50 . C49 . C54 . 119.1(4) yes C49 . C50 . C51 . 119.5(4) yes C49 . C50 . H501 . 120.250 no C51 . C50 . H501 . 120.250 no C50 . C51 . C52 . 121.3(4) yes C50 . C51 . H511 . 119.339 no C52 . C51 . H511 . 119.339 no C51 . C52 . C53 . 119.3(4) yes C51 . C52 . H521 . 120.341 no C53 . C52 . H521 . 120.342 no C52 . C53 . C54 . 119.8(4) yes C52 . C53 . H531 . 120.098 no C54 . C53 . H531 . 120.099 no C49 . C54 . C53 . 121.0(4) yes C49 . C54 . H541 . 119.510 no C53 . C54 . H541 . 119.511 no C48 . C55 . C56 . 119.7(3) yes C48 . C55 . C60 . 121.9(3) yes C56 . C55 . C60 . 117.9(3) yes C55 . C56 . C57 . 121.7(4) yes C55 . C56 . H561 . 119.130 no C57 . C56 . H561 . 119.130 no C56 . C57 . C58 . 119.5(4) yes C56 . C57 . H571 . 120.265 no C58 . C57 . H571 . 120.265 no C57 . C58 . C59 . 119.8(4) yes C57 . C58 . H581 . 120.103 no C59 . C58 . H581 . 120.102 no C58 . C59 . C60 . 120.4(4) yes C58 . C59 . H591 . 119.802 no C60 . C59 . H591 . 119.802 no C55 . C60 . C59 . 120.6(4) yes C55 . C60 . H601 . 119.676 no C59 . C60 . H601 . 119.676 no C48 . C61 . C62 . 121.2(3) yes C48 . C61 . C66 . 120.1(3) yes C62 . C61 . C66 . 118.6(4) yes C61 . C62 . C63 . 120.2(4) yes C61 . C62 . H621 . 119.909 no C63 . C62 . H621 . 119.909 no C62 . C63 . C64 . 120.7(4) yes C62 . C63 . H631 . 119.637 no C64 . C63 . H631 . 119.637 no C63 . C64 . C65 . 119.8(4) yes C63 . C64 . H641 . 120.111 no C65 . C64 . H641 . 120.111 no C64 . C65 . C66 . 120.3(4) yes C64 . C65 . H651 . 119.837 no C66 . C65 . H651 . 119.837 no C61 . C66 . C65 . 120.4(4) yes C61 . C66 . H661 . 119.799 no C65 . C66 . H661 . 119.799 no # Attachment '8.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 602417' #========================================================================== # Diffractometer details #========================================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #========================================================================== # 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 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 8.8317(5) _cell_angle_alpha 90 _cell_length_b 10.1281(5) _cell_angle_beta 103.017(2) _cell_length_c 12.0240(7) _cell_angle_gamma 90 _cell_volume 1047.9 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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 ' 0.0020 0.0020 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 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 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 ' 0.0080 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 _chemical_formula_sum ' C21 H25 N1 O7 ' _chemical_formula_moiety ' C21 H25 N1 O7 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 403.43 _cell_measurement_reflns_used 7100 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 428.149 _exptl_absorpt_coefficient_mu 0.096 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _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 7100 _reflns_number_total 2486 # 2491 including systematic absences _diffrn_reflns_av_R_equivalents 0.037 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_gt 1803 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_diff_density_min -0.15 _refine_diff_density_max 0.16 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1803 _refine_ls_number_parameters 262 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0365 _refine_ls_goodness_of_fit_ref 1.0672 _refine_ls_shift/su_max 0.005134 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.417 0.158 0.134 ; _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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.2254(2) 0.6202(2) 0.48859(17) 0.0282 1.0000 Uani C1 0.2427(3) 0.7070(2) 0.5901(2) 0.0305 1.0000 Uani C2 0.1327(3) 0.8219(3) 0.5477(2) 0.0369 1.0000 Uani C3 0.0062(3) 0.7592(3) 0.4546(2) 0.0352 1.0000 Uani C4 0.0908(3) 0.6530(2) 0.4053(2) 0.0303 1.0000 Uani C5 0.2994(3) 0.4980(2) 0.4985(2) 0.0286 1.0000 Uani O1 0.2427(2) 0.40187(16) 0.44412(15) 0.0325 1.0000 Uani C6 0.4558(3) 0.4915(2) 0.5784(2) 0.0286 1.0000 Uani C7 0.4931(3) 0.3794(2) 0.6457(2) 0.0326 1.0000 Uani C8 0.6427(3) 0.3647(3) 0.7130(2) 0.0396 1.0000 Uani C9 0.7538(3) 0.4613(3) 0.7125(2) 0.0391 1.0000 Uani C10 0.7166(3) 0.5733(3) 0.6463(2) 0.0365 1.0000 Uani C11 0.5675(3) 0.5888(3) 0.5788(2) 0.0314 1.0000 Uani C12 0.1909(3) 0.6347(2) 0.6864(2) 0.0314 1.0000 Uani O2 0.1081(2) 0.5402(2) 0.67417(17) 0.0459 1.0000 Uani O3 0.2443(2) 0.69632(19) 0.78519(15) 0.0392 1.0000 Uani C13 0.1855(4) 0.6468(3) 0.8816(2) 0.0522 1.0000 Uani C14 0.2401(4) 0.7388(4) 0.9800(3) 0.0568 1.0000 Uani C15 0.0474(3) 0.6051(3) 0.2980(2) 0.0318 1.0000 Uani C16 -0.0926(3) 0.6613(3) 0.2201(2) 0.0377 1.0000 Uani O4 -0.2061(2) 0.7047(2) 0.24552(18) 0.0500 1.0000 Uani O5 -0.0718(2) 0.6640(3) 0.11251(18) 0.0594 1.0000 Uani C17 -0.1962(4) 0.7226(4) 0.0261(3) 0.0590 1.0000 Uani C18 -0.3117(5) 0.6216(4) -0.0264(3) 0.0684 1.0000 Uani C19 0.1321(3) 0.5047(3) 0.2446(2) 0.0330 1.0000 Uani O6 0.0734(2) 0.4082(2) 0.19446(17) 0.0463 1.0000 Uani O7 0.2820(2) 0.53849(17) 0.25515(15) 0.0336 1.0000 Uani C20 0.3777(3) 0.4414(3) 0.2132(3) 0.0416 1.0000 Uani C21 0.5396(4) 0.4874(3) 0.2500(3) 0.0541 1.0000 Uani H11 0.3525 0.7356 0.6209 0.0378 1.0000 Uiso H21 0.0879 0.8581 0.6107 0.0455 1.0000 Uiso H22 0.1876 0.8939 0.5156 0.0455 1.0000 Uiso H31 -0.0398 0.8256 0.3951 0.0433 1.0000 Uiso H32 -0.0778 0.7203 0.4879 0.0433 1.0000 Uiso H71 0.4130 0.3096 0.6458 0.0393 1.0000 Uiso H81 0.6700 0.2844 0.7618 0.0474 1.0000 Uiso H91 0.8614 0.4499 0.7602 0.0463 1.0000 Uiso H101 0.7967 0.6432 0.6469 0.0447 1.0000 Uiso H111 0.5405 0.6696 0.5306 0.0391 1.0000 Uiso H131 0.0693 0.6444 0.8611 0.0647 1.0000 Uiso H132 0.2266 0.5560 0.9025 0.0647 1.0000 Uiso H141 0.2015 0.7073 1.0474 0.0684 1.0000 Uiso H142 0.1990 0.8295 0.9584 0.0684 1.0000 Uiso H143 0.3563 0.7411 0.9998 0.0684 1.0000 Uiso H171 -0.2493 0.7921 0.0625 0.0698 1.0000 Uiso H172 -0.1506 0.7636 -0.0346 0.0698 1.0000 Uiso H181 -0.3956 0.6642 -0.0853 0.0799 1.0000 Uiso H182 -0.3580 0.5805 0.0338 0.0799 1.0000 Uiso H183 -0.2593 0.5520 -0.0633 0.0799 1.0000 Uiso H201 0.3470 0.4360 0.1280 0.0526 1.0000 Uiso H202 0.3659 0.3526 0.2466 0.0526 1.0000 Uiso H211 0.6103 0.4238 0.2231 0.0668 1.0000 Uiso H212 0.5497 0.5765 0.2166 0.0668 1.0000 Uiso H213 0.5686 0.4932 0.3352 0.0668 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 N1 0.028(1) 0.026(1) 0.032(1) -0.0016(8) 0.0098(8) 0.0026(8) C1 0.0341(12) 0.0247(12) 0.0356(12) -0.003(1) 0.014(1) 0.001(1) C2 0.0465(15) 0.0268(13) 0.0405(14) -0.0019(11) 0.0165(12) 0.0066(12) C3 0.0359(13) 0.0337(13) 0.0386(14) 0.0023(11) 0.0136(11) 0.0090(11) C4 0.0296(12) 0.0262(12) 0.0377(13) 0.003(1) 0.013(1) 0.001(1) C5 0.0308(12) 0.0274(12) 0.0313(12) 0.004(1) 0.015(1) 0.000(1) O1 0.0370(9) 0.0241(9) 0.0382(9) 0.0003(8) 0.0120(8) -0.0022(7) C6 0.0302(12) 0.0272(12) 0.0313(12) -0.001(1) 0.013(1) 0.003(1) C7 0.0387(14) 0.0273(13) 0.0324(13) 0.0010(11) 0.0092(11) 0.0026(11) C8 0.0499(16) 0.0326(14) 0.0361(14) 0.0031(11) 0.0089(12) 0.0059(13) C9 0.0346(14) 0.0430(15) 0.0380(15) -0.0049(12) 0.0049(12) 0.0074(12) C10 0.0293(13) 0.0397(15) 0.0429(14) -0.0039(12) 0.0130(11) -0.0018(11) C11 0.0321(13) 0.0307(13) 0.0348(12) 0.0022(11) 0.015(1) 0.003(1) C12 0.0322(12) 0.0283(13) 0.0356(13) 0.000(1) 0.011(1) 0.0042(11) O2 0.0587(12) 0.0391(11) 0.0451(11) -0.0076(9) 0.022(1) -0.018(1) O3 0.0485(11) 0.038(1) 0.0335(9) -0.0019(8) 0.0136(8) -0.0099(9) C13 0.076(2) 0.0464(17) 0.0395(16) 0.0030(14) 0.0240(15) -0.0095(17) C14 0.065(2) 0.072(2) 0.0342(15) -0.0063(16) 0.0121(14) -0.0095(19) C15 0.0281(12) 0.0318(13) 0.0371(13) 0.0024(11) 0.011(1) 0.001(1) C16 0.0338(13) 0.0379(14) 0.0419(14) 0.0048(12) 0.0099(11) -0.0009(12) O4 0.0288(9) 0.0660(14) 0.0537(12) -0.0076(11) 0.0062(8) 0.007(1) O5 0.0468(11) 0.0886(19) 0.0447(11) 0.0261(12) 0.0144(9) 0.0211(12) C17 0.0512(18) 0.074(2) 0.0497(18) 0.0302(18) 0.0063(14) 0.0150(18) C18 0.093(3) 0.066(2) 0.0412(17) 0.0034(17) 0.0035(17) 0.021(2) C19 0.0350(14) 0.0341(14) 0.0307(13) 0.0030(11) 0.009(1) 0.0006(11) O6 0.0450(11) 0.0440(12) 0.0475(11) -0.014(1) 0.0055(9) -0.004(1) O7 0.0348(9) 0.0285(9) 0.042(1) -0.0023(8) 0.0185(8) 0.0032(8) C20 0.0456(16) 0.0325(13) 0.0533(17) -0.0054(12) 0.0248(14) 0.0055(12) C21 0.0448(16) 0.0520(19) 0.070(2) -0.0050(17) 0.0232(15) 0.0127(15) _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 N1 . C1 . 1.483(3) yes N1 . C4 . 1.411(3) yes N1 . C5 . 1.392(3) yes C1 . C2 . 1.528(3) yes C1 . C12 . 1.525(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.530(4) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.505(4) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C15 . 1.350(3) yes C5 . O1 . 1.217(3) yes C5 . C6 . 1.496(3) yes C6 . C7 . 1.390(3) yes C6 . C11 . 1.393(3) yes C7 . C8 . 1.393(4) yes C7 . H71 . 1.000 no C8 . C9 . 1.386(4) yes C8 . H81 . 1.000 no C9 . C10 . 1.382(4) yes C9 . H91 . 1.000 no C10 . C11 . 1.391(4) yes C10 . H101 . 1.000 no C11 . H111 . 1.000 no C12 . O2 . 1.192(3) yes C12 . O3 . 1.331(3) yes O3 . C13 . 1.462(3) yes C13 . C14 . 1.497(5) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . C16 . 1.486(4) yes C15 . C19 . 1.491(4) yes C16 . O4 . 1.196(3) yes C16 . O5 . 1.347(3) yes O5 . C17 . 1.457(3) yes C17 . C18 . 1.482(6) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . O6 . 1.203(3) yes C19 . O7 . 1.345(3) yes O7 . C20 . 1.459(3) yes C20 . C21 . 1.474(4) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 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 C1 . N1 . C4 . 111.02(19) yes C1 . N1 . C5 . 119.8(2) yes C4 . N1 . C5 . 125.1(2) yes N1 . C1 . C2 . 103.7(2) yes N1 . C1 . C12 . 110.3(2) yes C2 . C1 . C12 . 110.0(2) yes N1 . C1 . H11 . 112.8 no C2 . C1 . H11 . 113.1 no C12 . C1 . H11 . 106.8 no C1 . C2 . C3 . 103.4(2) yes C1 . C2 . H21 . 111.0 no C3 . C2 . H21 . 111.0 no C1 . C2 . H22 . 111.0 no C3 . C2 . H22 . 111.0 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 103.9(2) yes C2 . C3 . H31 . 110.9 no C4 . C3 . H31 . 110.9 no C2 . C3 . H32 . 110.9 no C4 . C3 . H32 . 110.9 no H31 . C3 . H32 . 109.5 no N1 . C4 . C3 . 107.5(2) yes N1 . C4 . C15 . 127.3(2) yes C3 . C4 . C15 . 125.0(2) yes N1 . C5 . O1 . 122.5(2) yes N1 . C5 . C6 . 116.2(2) yes O1 . C5 . C6 . 121.2(2) yes C5 . C6 . C7 . 118.2(2) yes C5 . C6 . C11 . 121.4(2) yes C7 . C6 . C11 . 120.1(2) yes C6 . C7 . C8 . 119.6(2) yes C6 . C7 . H71 . 120.2 no C8 . C7 . H71 . 120.2 no C7 . C8 . C9 . 120.1(3) yes C7 . C8 . H81 . 119.9 no C9 . C8 . H81 . 119.9 no C8 . C9 . C10 . 120.3(2) yes C8 . C9 . H91 . 119.8 no C10 . C9 . H91 . 119.8 no C9 . C10 . C11 . 120.0(2) yes C9 . C10 . H101 . 120.0 no C11 . C10 . H101 . 120.0 no C6 . C11 . C10 . 119.9(2) yes C6 . C11 . H111 . 120.1 no C10 . C11 . H111 . 120.1 no C1 . C12 . O2 . 124.9(2) yes C1 . C12 . O3 . 110.2(2) yes O2 . C12 . O3 . 124.8(2) yes C12 . O3 . C13 . 115.4(2) yes O3 . C13 . C14 . 107.7(3) yes O3 . C13 . H131 . 109.9 no C14 . C13 . H131 . 109.9 no O3 . C13 . H132 . 109.9 no C14 . C13 . H132 . 109.9 no H131 . C13 . H132 . 109.5 no C13 . C14 . H141 . 109.5 no C13 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C13 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C4 . C15 . C16 . 118.8(2) yes C4 . C15 . C19 . 126.4(2) yes C16 . C15 . C19 . 114.6(2) yes C15 . C16 . O4 . 127.3(3) yes C15 . C16 . O5 . 109.9(2) yes O4 . C16 . O5 . 122.8(3) yes C16 . O5 . C17 . 116.7(2) yes O5 . C17 . C18 . 111.0(3) yes O5 . C17 . H171 . 109.1 no C18 . C17 . H171 . 109.1 no O5 . C17 . H172 . 109.1 no C18 . C17 . H172 . 109.1 no H171 . C17 . H172 . 109.5 no C17 . C18 . H181 . 109.5 no C17 . C18 . H182 . 109.5 no H181 . C18 . H182 . 109.5 no C17 . C18 . H183 . 109.5 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no C15 . C19 . O6 . 124.6(2) yes C15 . C19 . O7 . 111.4(2) yes O6 . C19 . O7 . 123.9(2) yes C19 . O7 . C20 . 115.5(2) yes O7 . C20 . C21 . 106.4(2) yes O7 . C20 . H201 . 110.2 no C21 . C20 . H201 . 110.2 no O7 . C20 . H202 . 110.2 no C21 . C20 . H202 . 110.2 no H201 . C20 . H202 . 109.5 no C20 . C21 . H211 . 109.5 no C20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C20 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no