# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_trail-1 _database_code_depnum_ccdc_archive 'CCDC 907975' #TrackingRef 'chenna 4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 N O6' _chemical_formula_sum 'C20 H27 N O6' _chemical_formula_weight 377.43 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.065(2) _cell_length_b 12.172(2) _cell_length_c 13.880(3) _cell_angle_alpha 92.523(4) _cell_angle_beta 99.861(5) _cell_angle_gamma 95.377(4) _cell_volume 1995.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4123 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28845 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7050 _reflns_number_gt 4373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7050 _refine_ls_number_parameters 495 _refine_ls_number_restraints 67 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.2977 _refine_ls_wR_factor_gt 0.2683 _refine_ls_goodness_of_fit_ref 1.828 _refine_ls_restrained_S_all 1.888 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2183(3) 0.9742(2) 1.1168(2) 0.0589(9) Uani 1 1 d . . . C10 C 0.0281(4) 0.6162(3) 0.9033(3) 0.0449(10) Uani 1 1 d U . . C9 C 0.1370(4) 0.6651(3) 0.9255(3) 0.0428(10) Uani 1 1 d U . . C12 C -0.0023(4) 0.5164(3) 0.8488(3) 0.0515(11) Uani 1 1 d U . . C15 C 0.2156(4) 0.6061(4) 0.8880(3) 0.0474(10) Uani 1 1 d U . . C13 C 0.0762(4) 0.4602(4) 0.8118(3) 0.0597(13) Uani 1 1 d U . . H6 H 0.0560 0.3936 0.7748 0.072 Uiso 1 1 calc R . . C14 C 0.1873(4) 0.5079(4) 0.8325(3) 0.0574(12) Uani 1 1 d U . . H7 H 0.2433 0.4730 0.8085 0.069 Uiso 1 1 calc R . . O3 O -0.0662(3) 0.6556(2) 0.9277(2) 0.0603(9) Uani 1 1 d . . . O4 O -0.1169(3) 0.4897(2) 0.8372(2) 0.0661(10) Uani 1 1 d . . . C11 C -0.1579(4) 0.5772(4) 0.8874(4) 0.0689(15) Uani 1 1 d . . . H8A H -0.2127 0.6118 0.8423 0.083 Uiso 1 1 calc R . . H8B H -0.1950 0.5485 0.9391 0.083 Uiso 1 1 calc R . . C5 C 0.1838(5) 0.8726(4) 0.9146(4) 0.0731(15) Uani 1 1 d U . . H9A H 0.2353 0.9323 0.9507 0.088 Uiso 1 1 calc R . . H9B H 0.2148 0.8485 0.8582 0.088 Uiso 1 1 calc R . . C3 C 0.0786(5) 0.9980(4) 0.8000(4) 0.0763(15) Uani 1 1 d U . . H11A H 0.1056 0.9628 0.7456 0.092 Uiso 1 1 calc R . . H11B H 0.0028 1.0165 0.7758 0.092 Uiso 1 1 calc R . . C4 C 0.0722(5) 0.9102(5) 0.8833(5) 0.0837(17) Uani 1 1 d U . . H10A H 0.0470 0.9445 0.9390 0.100 Uiso 1 1 calc R . . H10B H 0.0181 0.8474 0.8575 0.100 Uiso 1 1 calc R . . C2 C 0.1505(7) 1.0990(6) 0.8319(5) 0.111(2) Uani 1 1 d U . . H12A H 0.2271 1.0793 0.8499 0.133 Uiso 1 1 calc R . . H12B H 0.1495 1.1434 0.7755 0.133 Uiso 1 1 calc R . . O5 O 0.3298(3) 0.6512(3) 0.9068(2) 0.0562(8) Uani 1 1 d . . . C16 C 0.3911(4) 0.6249(4) 0.9951(3) 0.0494(11) Uani 1 1 d . . . O6 O 0.3500(3) 0.5661(3) 1.0494(2) 0.0639(9) Uani 1 1 d . . . N1 N 0.4967(3) 0.6721(3) 1.0095(3) 0.0569(10) Uani 1 1 d . . . C17 C 0.5426(4) 0.7415(5) 0.9395(4) 0.0709(14) Uani 1 1 d U . . H16A H 0.5047 0.7166 0.8737 0.085 Uiso 1 1 calc R . . H16B H 0.6223 0.7325 0.9437 0.085 Uiso 1 1 calc R . . C19 C 0.5692(4) 0.6542(5) 1.1027(4) 0.0771(16) Uani 1 1 d U . . H14A H 0.6477 0.6656 1.0948 0.093 Uiso 1 1 calc R . . H14B H 0.5539 0.5782 1.1187 0.093 Uiso 1 1 calc R . . C20 C 0.5517(6) 0.7292(5) 1.1855(4) 0.101(2) Uani 1 1 d U . . H15A H 0.5694 0.8047 1.1712 0.151 Uiso 1 1 calc R . . H15B H 0.6003 0.7133 1.2445 0.151 Uiso 1 1 calc R . . H15C H 0.4743 0.7180 1.1942 0.151 Uiso 1 1 calc R . . C18 C 0.5296(6) 0.8617(5) 0.9562(5) 0.0915(19) Uani 1 1 d U . . H17A H 0.4512 0.8711 0.9546 0.137 Uiso 1 1 calc R . . H17B H 0.5569 0.9024 0.9058 0.137 Uiso 1 1 calc R . . H17C H 0.5723 0.8887 1.0190 0.137 Uiso 1 1 calc R . . C6 C 0.1680(4) 0.7745(3) 0.9814(3) 0.0462(10) Uani 1 1 d U . . C7 C 0.1906(4) 0.7797(3) 1.0756(3) 0.0477(11) Uani 1 1 d U . . H19 H 0.1894 0.7124 1.1050 0.057 Uiso 1 1 calc R . . C8 C 0.2181(4) 0.8795(3) 1.1421(3) 0.0472(11) Uani 1 1 d U . . O2 O 0.2430(4) 0.8575(2) 1.2341(2) 0.0759(12) Uani 1 1 d . . . H6A H 0.2554 0.9154 1.2684 0.114 Uiso 1 1 calc R . . C1 C 0.1292(7) 1.1671(6) 0.9090(6) 0.115(2) Uani 1 1 d U . . H21A H 0.0524 1.1849 0.8952 0.173 Uiso 1 1 calc R . . H21B H 0.1797 1.2339 0.9162 0.173 Uiso 1 1 calc R . . H21C H 0.1408 1.1292 0.9686 0.173 Uiso 1 1 calc R . . C30 C 0.5152(4) 0.3792(3) 0.5895(3) 0.0436(10) Uani 1 1 d U . . C29 C 0.4061(4) 0.3437(3) 0.5419(3) 0.0400(9) Uani 1 1 d U . . C32 C 0.5421(4) 0.4746(3) 0.6475(3) 0.0447(10) Uani 1 1 d U . . C35 C 0.3262(4) 0.4156(3) 0.5587(3) 0.0439(10) Uani 1 1 d U . . C33 C 0.4637(4) 0.5427(3) 0.6637(3) 0.0524(11) Uani 1 1 d U . . H27 H 0.4830 0.6075 0.7036 0.063 Uiso 1 1 calc R . . C34 C 0.3524(4) 0.5106(4) 0.6175(3) 0.0518(11) Uani 1 1 d U . . H26 H 0.2956 0.5543 0.6270 0.062 Uiso 1 1 calc R . . C31 C 0.6991(4) 0.3930(4) 0.6498(4) 0.0716(16) Uani 1 1 d . . . H28A H 0.7258 0.3512 0.7055 0.086 Uiso 1 1 calc R . . H28B H 0.7620 0.4122 0.6165 0.086 Uiso 1 1 calc R . . O10 O 0.6568(3) 0.4901(2) 0.6819(2) 0.0579(9) Uani 1 1 d . . . O9 O 0.6107(3) 0.3283(2) 0.5846(2) 0.0600(9) Uani 1 1 d . . . O12 O 0.2133(2) 0.3889(2) 0.5122(2) 0.0525(8) Uani 1 1 d . . . O11 O 0.1759(3) 0.3095(3) 0.6493(2) 0.0689(10) Uani 1 1 d . . . C36 C 0.1445(4) 0.3318(4) 0.5666(4) 0.0591(13) Uani 1 1 d . . . N2 N 0.0392(4) 0.3101(5) 0.5169(3) 0.1008(19) Uani 1 1 d . . . C39 C -0.0458(7) 0.2463(8) 0.5659(5) 0.127(3) Uani 1 1 d U . . H30A H -0.0356 0.2719 0.6344 0.153 Uiso 1 1 calc R . . H30B H -0.1217 0.2582 0.5349 0.153 Uiso 1 1 calc R . . C38 C -0.0023(9) 0.2773(7) 0.3593(8) 0.171(4) Uani 1 1 d U . . H33A H 0.0115 0.3005 0.2968 0.257 Uiso 1 1 calc R . . H33B H -0.0729 0.2314 0.3507 0.257 Uiso 1 1 calc R . . H33C H 0.0578 0.2362 0.3881 0.257 Uiso 1 1 calc R . . C37 C -0.0066(7) 0.3634(7) 0.4164(6) 0.128(3) Uani 1 1 d U . . H32A H -0.0830 0.3836 0.4131 0.154 Uiso 1 1 calc R . . H32B H 0.0430 0.4265 0.4039 0.154 Uiso 1 1 calc R . . C40 C -0.0313(7) 0.1301(8) 0.5584(6) 0.143(3) Uani 1 1 d U . . H31A H -0.0466 0.1040 0.4907 0.215 Uiso 1 1 calc R . . H31B H -0.0827 0.0899 0.5931 0.215 Uiso 1 1 calc R . . H31C H 0.0450 0.1192 0.5864 0.215 Uiso 1 1 calc R . . O8 O 0.2603(3) 0.1605(3) 0.2312(2) 0.0674(10) Uani 1 1 d . . . H11 H 0.3164 0.1807 0.2080 0.101 Uiso 1 1 calc R . . O7 O 0.2899(3) 0.0430(2) 0.3471(2) 0.0677(10) Uani 1 1 d . . . C28 C 0.2915(4) 0.1380(4) 0.3232(3) 0.0502(11) Uani 1 1 d U . . C26 C 0.3782(4) 0.2374(3) 0.4822(3) 0.0459(10) Uani 1 1 d U . . C27 C 0.3249(4) 0.2368(3) 0.3901(3) 0.0472(11) Uani 1 1 d U . . H35 H 0.3073 0.3044 0.3661 0.057 Uiso 1 1 calc R . . C25 C 0.4089(5) 0.1356(3) 0.5351(3) 0.0630(14) Uani 1 1 d U . . H37A H 0.4294 0.0818 0.4893 0.076 Uiso 1 1 calc R . . H37B H 0.4742 0.1555 0.5863 0.076 Uiso 1 1 calc R . . C24 C 0.3140(7) 0.0850(4) 0.5792(5) 0.106(2) Uani 1 1 d U . . H24A H 0.2437 0.0926 0.5354 0.127 Uiso 1 1 calc R . . H24B H 0.3127 0.1267 0.6401 0.127 Uiso 1 1 calc R . . C23 C 0.3178(11) -0.0335(6) 0.5998(6) 0.197(6) Uani 1 1 d DU . . H23A H 0.2405 -0.0658 0.5963 0.236 Uiso 1 1 calc R . . H23B H 0.3470 -0.0694 0.5470 0.236 Uiso 1 1 calc R . . C21 C 0.3730(9) -0.1880(6) 0.6883(6) 0.151(4) Uani 1 1 d DU . . H21D H 0.3641 -0.2234 0.6239 0.226 Uiso 1 1 calc R . . H21E H 0.3110 -0.2144 0.7191 0.226 Uiso 1 1 calc R . . H21F H 0.4428 -0.2047 0.7267 0.226 Uiso 1 1 calc R . . C22 C 0.3750(11) -0.0592(8) 0.6806(6) 0.215(7) Uani 1 1 d DU . . H22A H 0.3443 -0.0279 0.7347 0.258 Uiso 1 1 calc R . . H22B H 0.4526 -0.0271 0.6862 0.258 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.086(2) 0.0384(17) 0.0443(17) -0.0124(14) 0.0021(15) -0.0110(15) C10 0.052(3) 0.036(2) 0.045(2) -0.0055(18) 0.004(2) 0.0041(19) C9 0.051(3) 0.039(2) 0.035(2) -0.0045(17) 0.0005(18) -0.0017(19) C12 0.052(3) 0.041(2) 0.052(3) -0.012(2) -0.012(2) -0.002(2) C15 0.046(3) 0.052(3) 0.040(2) -0.0041(19) 0.0009(19) 0.000(2) C13 0.065(3) 0.049(3) 0.057(3) -0.022(2) -0.007(2) 0.009(2) C14 0.063(3) 0.058(3) 0.048(3) -0.014(2) 0.001(2) 0.014(2) O3 0.050(2) 0.0418(17) 0.085(2) -0.0198(16) 0.0115(17) -0.0055(15) O4 0.053(2) 0.0469(19) 0.087(2) -0.0184(17) -0.0100(17) -0.0040(15) C11 0.054(3) 0.050(3) 0.096(4) -0.012(3) 0.008(3) -0.008(2) C5 0.075(4) 0.068(3) 0.068(3) -0.016(2) 0.004(3) -0.007(3) C3 0.090(4) 0.056(3) 0.083(4) 0.015(3) 0.012(3) 0.007(3) C4 0.070(4) 0.073(3) 0.098(4) -0.013(3) -0.006(3) -0.002(3) C2 0.135(7) 0.090(5) 0.101(5) 0.017(4) 0.004(5) 0.007(4) O5 0.050(2) 0.066(2) 0.0496(18) -0.0015(15) 0.0046(14) -0.0002(15) C16 0.048(3) 0.052(3) 0.044(3) -0.003(2) -0.001(2) 0.004(2) O6 0.051(2) 0.068(2) 0.066(2) 0.0145(18) -0.0047(16) -0.0070(16) N1 0.049(2) 0.065(2) 0.055(2) 0.0044(19) 0.0080(19) 0.0016(19) C17 0.050(3) 0.086(4) 0.075(3) 0.006(3) 0.013(3) -0.003(3) C19 0.044(3) 0.094(4) 0.084(4) 0.018(3) -0.009(3) -0.006(3) C20 0.131(6) 0.096(5) 0.057(3) 0.008(3) -0.011(3) -0.031(4) C18 0.098(5) 0.076(4) 0.094(4) 0.013(3) 0.008(4) -0.012(3) C6 0.052(3) 0.037(2) 0.043(2) -0.0073(17) 0.0002(19) -0.0053(19) C7 0.056(3) 0.037(2) 0.044(2) -0.0072(18) -0.002(2) -0.0007(19) C8 0.057(3) 0.039(2) 0.040(2) -0.0092(19) 0.001(2) -0.001(2) O2 0.135(3) 0.0376(17) 0.0427(19) -0.0124(14) -0.0102(19) -0.0002(19) C1 0.115(6) 0.104(5) 0.132(6) -0.003(4) 0.044(5) 0.009(4) C30 0.053(3) 0.032(2) 0.043(2) -0.0010(17) 0.0039(19) -0.0009(19) C29 0.050(3) 0.035(2) 0.032(2) -0.0026(16) 0.0033(17) -0.0042(18) C32 0.052(3) 0.033(2) 0.041(2) -0.0057(18) -0.0038(19) -0.0077(19) C35 0.051(3) 0.040(2) 0.037(2) -0.0022(17) 0.0011(19) -0.0046(19) C33 0.065(3) 0.037(2) 0.051(3) -0.0147(19) 0.009(2) -0.006(2) C34 0.055(3) 0.045(2) 0.052(3) -0.011(2) 0.005(2) 0.003(2) C31 0.059(3) 0.048(3) 0.095(4) -0.012(3) -0.019(3) 0.003(2) O10 0.053(2) 0.0462(18) 0.0629(19) -0.0085(15) -0.0126(15) -0.0048(15) O9 0.051(2) 0.0476(18) 0.073(2) -0.0139(15) -0.0086(16) 0.0067(15) O12 0.0488(19) 0.0614(19) 0.0428(16) -0.0055(14) 0.0023(14) -0.0023(15) O11 0.070(2) 0.084(2) 0.045(2) -0.0089(17) 0.0063(16) -0.0192(18) C36 0.055(3) 0.070(3) 0.046(3) -0.016(2) 0.006(2) -0.010(2) N2 0.066(3) 0.169(5) 0.050(3) 0.003(3) -0.004(2) -0.048(3) C39 0.092(5) 0.202(8) 0.069(4) -0.033(5) 0.009(4) -0.053(6) C38 0.175(10) 0.099(6) 0.246(13) -0.007(6) 0.086(9) -0.031(6) C37 0.123(7) 0.126(7) 0.120(6) -0.020(5) 0.016(5) -0.046(5) C40 0.110(6) 0.204(8) 0.092(5) -0.008(6) -0.007(4) -0.054(7) O8 0.100(3) 0.0483(19) 0.0444(19) -0.0056(15) -0.0023(17) -0.0100(19) O7 0.110(3) 0.0391(18) 0.0450(18) -0.0137(14) -0.0002(17) -0.0082(17) C28 0.058(3) 0.040(3) 0.049(3) -0.007(2) 0.006(2) -0.008(2) C26 0.054(3) 0.033(2) 0.048(2) -0.0072(18) 0.007(2) -0.0039(18) C27 0.061(3) 0.032(2) 0.042(2) -0.0085(17) 0.002(2) -0.0076(19) C25 0.094(4) 0.036(2) 0.049(3) -0.011(2) -0.009(2) 0.006(2) C24 0.180(7) 0.051(3) 0.090(4) 0.024(3) 0.040(5) -0.006(4) C23 0.410(18) 0.090(5) 0.111(6) 0.049(5) 0.081(8) 0.052(7) C21 0.253(11) 0.116(6) 0.109(6) 0.047(5) 0.054(6) 0.090(7) C22 0.404(19) 0.176(8) 0.099(6) 0.043(6) 0.053(9) 0.181(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.219(5) . ? C10 O3 1.364(5) . ? C10 C9 1.369(6) . ? C10 C12 1.387(6) . ? C9 C15 1.397(6) . ? C9 C6 1.494(5) . ? C12 O4 1.370(5) . ? C12 C13 1.373(6) . ? C15 C14 1.376(6) . ? C15 O5 1.411(5) . ? C13 C14 1.386(7) . ? O3 C11 1.411(5) . ? O4 C11 1.420(6) . ? C5 C4 1.464(8) . ? C5 C6 1.560(7) . ? C3 C2 1.443(8) . ? C3 C4 1.615(8) . ? C2 C1 1.398(9) . ? O5 C16 1.386(5) . ? C16 O6 1.198(5) . ? C16 N1 1.325(6) . ? N1 C17 1.461(6) . ? N1 C19 1.469(6) . ? C17 C18 1.498(8) . ? C19 C20 1.492(8) . ? C6 C7 1.286(6) . ? C7 C8 1.470(5) . ? C8 O2 1.306(5) . ? C30 C32 1.364(5) . ? C30 O9 1.368(5) . ? C30 C29 1.387(6) . ? C29 C35 1.403(6) . ? C29 C26 1.484(5) . ? C32 C33 1.355(6) . ? C32 O10 1.376(5) . ? C35 C34 1.365(6) . ? C35 O12 1.406(5) . ? C33 C34 1.397(6) . ? C31 O10 1.415(5) . ? C31 O9 1.423(5) . ? O12 C36 1.378(6) . ? O11 C36 1.197(5) . ? C36 N2 1.334(6) . ? N2 C39 1.501(9) . ? N2 C37 1.599(9) . ? C39 C40 1.442(12) . ? C38 C37 1.296(10) . ? O8 C28 1.317(5) . ? O7 C28 1.216(5) . ? C28 C27 1.468(5) . ? C26 C27 1.328(6) . ? C26 C25 1.511(6) . ? C25 C24 1.486(8) . ? C24 C23 1.487(9) . ? C23 C22 1.280(10) . ? C21 C22 1.575(10) . ? 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 O3 C10 C9 127.3(4) . . ? O3 C10 C12 109.3(4) . . ? C9 C10 C12 123.3(4) . . ? C10 C9 C15 114.2(4) . . ? C10 C9 C6 122.8(4) . . ? C15 C9 C6 123.0(4) . . ? O4 C12 C13 128.6(4) . . ? O4 C12 C10 109.9(4) . . ? C13 C12 C10 121.5(4) . . ? C14 C15 C9 123.5(4) . . ? C14 C15 O5 118.5(4) . . ? C9 C15 O5 117.9(4) . . ? C12 C13 C14 116.6(4) . . ? C15 C14 C13 120.8(4) . . ? C10 O3 C11 106.3(3) . . ? C12 O4 C11 105.4(3) . . ? O3 C11 O4 109.0(4) . . ? C4 C5 C6 107.2(5) . . ? C2 C3 C4 114.9(5) . . ? C5 C4 C3 109.8(5) . . ? C1 C2 C3 120.3(7) . . ? C16 O5 C15 114.7(3) . . ? O6 C16 N1 126.3(4) . . ? O6 C16 O5 122.0(4) . . ? N1 C16 O5 111.7(4) . . ? C16 N1 C17 123.8(4) . . ? C16 N1 C19 117.0(4) . . ? C17 N1 C19 119.2(4) . . ? N1 C17 C18 113.3(5) . . ? N1 C19 C20 113.1(5) . . ? C7 C6 C9 120.1(4) . . ? C7 C6 C5 126.1(4) . . ? C9 C6 C5 113.4(4) . . ? C6 C7 C8 127.5(4) . . ? O1 C8 O2 121.9(4) . . ? O1 C8 C7 125.2(4) . . ? O2 C8 C7 113.0(4) . . ? C32 C30 O9 109.9(4) . . ? C32 C30 C29 123.2(4) . . ? O9 C30 C29 126.8(4) . . ? C30 C29 C35 113.6(3) . . ? C30 C29 C26 122.2(4) . . ? C35 C29 C26 124.1(4) . . ? C33 C32 C30 122.5(4) . . ? C33 C32 O10 127.3(4) . . ? C30 C32 O10 110.2(4) . . ? C34 C35 C29 123.4(4) . . ? C34 C35 O12 118.2(4) . . ? C29 C35 O12 118.4(3) . . ? C32 C33 C34 116.6(4) . . ? C35 C34 C33 120.7(4) . . ? O10 C31 O9 108.6(4) . . ? C32 O10 C31 105.1(3) . . ? C30 O9 C31 105.4(3) . . ? C36 O12 C35 115.4(3) . . ? O11 C36 N2 125.4(5) . . ? O11 C36 O12 123.2(4) . . ? N2 C36 O12 111.3(4) . . ? C36 N2 C39 117.7(5) . . ? C36 N2 C37 124.0(5) . . ? C39 N2 C37 117.6(5) . . ? C40 C39 N2 109.5(7) . . ? C38 C37 N2 96.5(8) . . ? O7 C28 O8 121.0(4) . . ? O7 C28 C27 125.4(4) . . ? O8 C28 C27 113.5(4) . . ? C27 C26 C29 119.4(4) . . ? C27 C26 C25 125.0(4) . . ? C29 C26 C25 115.5(4) . . ? C26 C27 C28 125.1(4) . . ? C24 C25 C26 111.8(5) . . ? C25 C24 C23 115.7(7) . . ? C22 C23 C24 119.3(9) . . ? C23 C22 C21 112.3(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.912 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.072 data_trail-1b _database_code_depnum_ccdc_archive 'CCDC 907976' #TrackingRef 'chenna 4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O3' _chemical_formula_sum 'C14 H12 O3' _chemical_formula_weight 228.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.015(7) _cell_length_b 5.8478(19) _cell_length_c 17.370(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.391(6) _cell_angle_gamma 90.00 _cell_volume 2161.6(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 28.35 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9980 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18133 _diffrn_reflns_av_R_equivalents 0.1097 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2703 _reflns_number_gt 1151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2703 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1649 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1865 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C7 C 0.39308(12) 0.6839(5) 0.24180(17) 0.0314(7) Uani 1 1 d . . . C10 C 0.35228(13) 0.6773(5) 0.37477(18) 0.0354(7) Uani 1 1 d . . . C9 C 0.39167(14) 0.8563(5) 0.36794(19) 0.0379(7) Uani 1 1 d . . . C5 C 0.33593(13) 0.4970(5) 0.31635(18) 0.0360(7) Uani 1 1 d . . . C4 C 0.29630(15) 0.3219(6) 0.3241(2) 0.0426(8) Uani 1 1 d . . . C6 C 0.35838(13) 0.5062(5) 0.25060(18) 0.0359(7) Uani 1 1 d . . . C8 C 0.41120(13) 0.8603(5) 0.30305(18) 0.0330(7) Uani 1 1 d . . . C1 C 0.32795(16) 0.6736(6) 0.4388(2) 0.0459(8) Uani 1 1 d . . . C2 C 0.28974(15) 0.5025(6) 0.4433(2) 0.0498(9) Uani 1 1 d . . . C3 C 0.27426(15) 0.3234(7) 0.3857(2) 0.0482(9) Uani 1 1 d . . . O1 O 0.44831(10) 1.0299(4) 0.29297(13) 0.0417(6) Uani 1 1 d . . . C12 C 0.44225(13) 0.5278(5) 0.15183(18) 0.0310(7) Uani 1 1 d . . . C11 C 0.41105(13) 0.7013(5) 0.16813(17) 0.0319(7) Uani 1 1 d . . . C13 C 0.38930(18) 0.9121(6) 0.1162(2) 0.0390(8) Uani 1 1 d . . . C14 C 0.46591(13) 0.5142(5) 0.08486(17) 0.0318(7) Uani 1 1 d . . . O2 O 0.49765(10) 0.3467(3) 0.07975(12) 0.0385(5) Uani 1 1 d . . . O3 O 0.45303(10) 0.6843(3) 0.03278(13) 0.0396(6) Uani 1 1 d . . . H1 H 0.4069(13) 0.983(5) 0.4133(19) 0.047(8) Uiso 1 1 d . . . H7 H 0.4512(11) 0.396(4) 0.1860(15) 0.019(6) Uiso 1 1 d . . . H2 H 0.3394(13) 0.803(5) 0.4764(19) 0.045(9) Uiso 1 1 d . . . H3 H 0.2752(14) 0.533(5) 0.483(2) 0.047(9) Uiso 1 1 d . . . H6 H 0.4234(16) 0.992(5) 0.1139(19) 0.052(10) Uiso 1 1 d . . . H4 H 0.2844(13) 0.207(5) 0.2826(18) 0.040(9) Uiso 1 1 d . . . H5 H 0.3665(15) 1.012(6) 0.142(2) 0.063(10) Uiso 1 1 d . . . H8 H 0.3420(12) 0.380(4) 0.2054(18) 0.034(7) Uiso 1 1 d . . . H9 H 0.4733(17) 0.669(7) -0.006(2) 0.085(13) Uiso 1 1 d . . . H10 H 0.3619(16) 0.868(6) 0.059(2) 0.064(11) Uiso 1 1 d . . . H11 H 0.2473(17) 0.211(6) 0.387(2) 0.067(11) Uiso 1 1 d . . . H12 H 0.463(2) 1.147(9) 0.347(3) 0.139(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0374(16) 0.0301(16) 0.0302(16) 0.0000(13) 0.0169(13) 0.0028(13) C10 0.0368(16) 0.0387(17) 0.0327(17) 0.0035(14) 0.0156(14) 0.0035(14) C9 0.0437(18) 0.0392(18) 0.0347(18) -0.0080(15) 0.0192(15) 0.0007(14) C5 0.0353(16) 0.0394(17) 0.0342(17) 0.0019(14) 0.0142(14) 0.0019(14) C4 0.0439(18) 0.0384(18) 0.045(2) 0.0056(17) 0.0161(16) -0.0005(16) C6 0.0395(17) 0.0374(17) 0.0322(17) -0.0047(14) 0.0152(14) 0.0014(14) C8 0.0367(16) 0.0309(16) 0.0351(17) 0.0011(13) 0.0177(14) 0.0027(13) C1 0.054(2) 0.048(2) 0.044(2) -0.0035(18) 0.0277(17) -0.0006(18) C2 0.0459(19) 0.066(2) 0.046(2) 0.0046(19) 0.0269(17) -0.0036(18) C3 0.0414(19) 0.056(2) 0.052(2) 0.0077(18) 0.0229(17) -0.0067(17) O1 0.0519(13) 0.0417(13) 0.0397(13) -0.0072(10) 0.0267(11) -0.0101(10) C12 0.0400(16) 0.0280(16) 0.0281(16) 0.0005(13) 0.0166(13) -0.0005(13) C11 0.0337(15) 0.0321(16) 0.0308(17) -0.0010(13) 0.0132(13) -0.0027(13) C13 0.046(2) 0.0376(19) 0.037(2) 0.0009(15) 0.0200(17) 0.0034(16) C14 0.0387(16) 0.0319(17) 0.0273(16) 0.0002(13) 0.0155(13) -0.0010(13) O2 0.0534(13) 0.0384(12) 0.0337(12) 0.0052(9) 0.0278(10) 0.0089(10) O3 0.0534(13) 0.0403(12) 0.0353(12) 0.0061(10) 0.0284(11) 0.0057(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 C6 1.354(4) . ? C7 C8 1.425(4) . ? C7 C11 1.491(4) . ? C10 C5 1.412(4) . ? C10 C9 1.419(4) . ? C10 C1 1.423(4) . ? C9 C8 1.364(4) . ? C5 C4 1.411(4) . ? C5 C6 1.423(4) . ? C4 C3 1.347(4) . ? C8 O1 1.363(3) . ? C1 C2 1.354(4) . ? C2 C3 1.397(5) . ? C12 C11 1.334(4) . ? C12 C14 1.462(4) . ? C11 C13 1.497(4) . ? C14 O2 1.245(3) . ? C14 O3 1.301(3) . ? 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 C6 C7 C8 119.2(2) . . ? C6 C7 C11 121.2(3) . . ? C8 C7 C11 119.6(2) . . ? C5 C10 C9 119.7(3) . . ? C5 C10 C1 118.3(3) . . ? C9 C10 C1 122.0(3) . . ? C8 C9 C10 120.3(3) . . ? C4 C5 C10 118.6(3) . . ? C4 C5 C6 123.4(3) . . ? C10 C5 C6 118.0(3) . . ? C3 C4 C5 121.6(3) . . ? C7 C6 C5 122.0(3) . . ? O1 C8 C9 122.6(3) . . ? O1 C8 C7 116.8(2) . . ? C9 C8 C7 120.7(3) . . ? C2 C1 C10 120.9(3) . . ? C1 C2 C3 120.5(3) . . ? C4 C3 C2 120.2(3) . . ? C11 C12 C14 127.2(3) . . ? C12 C11 C7 118.6(2) . . ? C12 C11 C13 125.6(3) . . ? C7 C11 C13 115.8(2) . . ? O2 C14 O3 122.5(2) . . ? O2 C14 C12 120.4(3) . . ? O3 C14 C12 117.1(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.219 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.050