# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 7.4870(15) _cell_length_b 16.276(3) _cell_length_c 11.153(2) _cell_angle_alpha 90 _cell_angle_beta 90.01(3) _cell_angle_gamma 90 _cell_volume 1359.1(5) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C31 H50 O4 # Dc = 1.19 Fooo = 536.00 Mu = 0.76 M = 486.74 # Found Formula = C31 H50 O4 # Dc = 1.19 FOOO = 536.00 Mu = 0.76 M = 486.74 _chemical_formula_sum 'C31 H50 O4' _chemical_formula_moiety 'C31 H50 O4' _chemical_compound_source ? _chemical_formula_weight 486.74 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.220 _exptl_crystal_size_mid 0.430 _exptl_crystal_size_max 0.510 _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 3262 _reflns_number_total 3252 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 3252 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 3129 _diffrn_reflns_theta_min 2.503 _diffrn_reflns_theta_max 27.520 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.520 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 3.46 _oxford_diffrn_Wilson_scale 3.87 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.34 _refine_diff_density_max 0.46 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3237 _refine_ls_number_restraints 1 _refine_ls_number_parameters 316 _oxford_refine_ls_R_factor_ref 0.0923 _refine_ls_wR_factor_ref 0.1995 _refine_ls_goodness_of_fit_ref 0.9688 _refine_ls_shift/su_max 0.0000812 _refine_ls_shift/su_mean 0.0000118 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3237 _refine_ls_R_factor_all 0.0923 _refine_ls_wR_factor_all 0.1995 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2631 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_gt 0.1774 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _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: 8.84 11.7 3.37 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C10 C -0.6101(5) 0.3454(3) -0.6288(3) 0.0348 1.0000 Uani . . . . . . C9 C -0.6428(5) 0.2647(2) -0.6982(3) 0.0327 1.0000 Uani . . . . . . C8 C -0.8442(5) 0.2379(3) -0.7062(3) 0.0345 1.0000 Uani . . . . . . C14 C -0.8583(5) 0.1644(3) -0.8003(4) 0.0361 1.0000 Uani . . . . . . C13 C -0.7391(5) 0.0922(2) -0.7550(4) 0.0362 1.0000 Uani . . . . . . C18 C -0.7561(6) 0.0151(3) -0.8346(4) 0.0381 1.0000 Uani . . . . . . C17 C -0.9508(6) -0.0127(3) -0.8547(4) 0.0460 1.0000 Uani . . . . . . C16 C -1.0745(6) 0.0571(4) -0.8885(6) 0.0564 1.0000 Uani . . . . . . C15 C -1.0540(6) 0.1329(4) -0.8089(5) 0.0540 1.0000 Uani . . . . . . C28 C -0.9868(9) -0.0526(4) -0.7307(5) 0.0667 1.0000 Uani . . . . . . O1 O -0.8190(7) -0.0820(3) -0.6866(3) 0.0676 1.0000 Uani . . . . . . C19 C -0.6830(7) -0.0620(3) -0.7752(4) 0.0450 1.0000 Uani . . . . . . C20 C -0.6595(8) -0.1347(3) -0.8614(4) 0.0520 1.0000 Uani . . . . . . C21 C -0.8436(8) -0.1554(3) -0.9169(5) 0.0580 1.0000 Uani . . . . . . C22 C -0.9498(7) -0.0793(3) -0.9530(5) 0.0516 1.0000 Uani . . . . . . C29 C -0.5220(8) -0.1118(4) -0.9586(5) 0.0634 1.0000 Uani . . . . . . C30 C -0.5904(13) -0.2100(3) -0.7933(7) 0.0819 1.0000 Uani . . . . . . C12 C -0.5434(6) 0.1191(3) -0.7428(4) 0.0409 1.0000 Uani . . . . . . C11 C -0.5254(6) 0.1923(3) -0.6575(4) 0.0419 1.0000 Uani . . . . . . C27 C -0.8019(7) 0.1907(3) -0.9274(4) 0.0456 1.0000 Uani . . . . . . C7 C -0.9579(6) 0.3120(3) -0.7499(5) 0.0463 1.0000 Uani . . . . . . C6 C -0.9232(6) 0.3933(3) -0.6818(5) 0.0483 1.0000 Uani . . . . . . C5 C -0.7245(6) 0.4116(3) -0.6902(4) 0.0386 1.0000 Uani . . . . . . C4 C -0.6518(6) 0.4972(3) -0.6540(4) 0.0422 1.0000 Uani . . . . . . C3 C -0.4458(6) 0.4767(3) -0.6272(4) 0.0403 1.0000 Uani . . . . . . C1 C -0.4234(6) 0.3833(3) -0.6525(4) 0.0390 1.0000 Uani . . . . . . C2 C -0.3263(5) 0.5284(3) -0.7099(4) 0.0429 1.0000 Uani . . . . . . O4 O -0.2798(6) 0.6000(3) -0.6600(4) 0.0600 1.0000 Uani . . . . . . C31 C -0.1771(9) 0.6555(4) -0.7352(6) 0.0658 1.0000 Uani . . . . . . O3 O -0.2841(6) 0.5097(3) -0.8092(4) 0.0623 1.0000 Uani . . . . . . O2 O -0.4056(5) 0.4984(2) -0.5053(3) 0.0496 1.0000 Uani . . . . . . C23 C -0.6793(8) 0.5567(3) -0.7592(6) 0.0598 1.0000 Uani . . . . . . C24 C -0.7434(7) 0.5347(4) -0.5435(6) 0.0614 1.0000 Uani . . . . . . C26 C -0.9193(7) 0.2106(3) -0.5832(4) 0.0490 1.0000 Uani . . . . . . C25 C -0.6356(7) 0.3373(3) -0.4910(4) 0.0507 1.0000 Uani . . . . . . H91 H -0.6083 0.2775 -0.7814 0.0387 1.0000 Uiso R . . . . . H131 H -0.7815 0.0774 -0.6747 0.0418 1.0000 Uiso R . . . . . H181 H -0.6958 0.0244 -0.9118 0.0456 1.0000 Uiso R . . . . . H161 H -1.0480 0.0731 -0.9709 0.0680 1.0000 Uiso R . . . . . H162 H -1.1965 0.0382 -0.8825 0.0680 1.0000 Uiso R . . . . . H151 H -1.1285 0.1768 -0.8405 0.0649 1.0000 Uiso R . . . . . H152 H -1.0948 0.1190 -0.7286 0.0651 1.0000 Uiso R . . . . . H282 H -1.0734 -0.0973 -0.7386 0.0801 1.0000 Uiso R . . . . . H281 H -1.0343 -0.0118 -0.6759 0.0800 1.0000 Uiso R . . . . . H191 H -0.5687 -0.0504 -0.7340 0.0536 1.0000 Uiso R . . . . . H212 H -0.8247 -0.1892 -0.9875 0.0708 1.0000 Uiso R . . . . . H211 H -0.9125 -0.1867 -0.8583 0.0712 1.0000 Uiso R . . . . . H221 H -1.0726 -0.0959 -0.9674 0.0627 1.0000 Uiso R . . . . . H222 H -0.8994 -0.0555 -1.0259 0.0630 1.0000 Uiso R . . . . . H291 H -0.4915 -0.1592 -1.0054 0.0948 1.0000 Uiso R . . . . . H292 H -0.5707 -0.0701 -1.0117 0.0950 1.0000 Uiso R . . . . . H293 H -0.4154 -0.0909 -0.9210 0.0950 1.0000 Uiso R . . . . . H301 H -0.5981 -0.2584 -0.8431 0.1250 1.0000 Uiso R . . . . . H302 H -0.6613 -0.2189 -0.7219 0.1249 1.0000 Uiso R . . . . . H303 H -0.4669 -0.2022 -0.7702 0.1250 1.0000 Uiso R . . . . . H121 H -0.4982 0.1334 -0.8219 0.0499 1.0000 Uiso R . . . . . H122 H -0.4762 0.0730 -0.7114 0.0503 1.0000 Uiso R . . . . . H112 H -0.4026 0.2098 -0.6555 0.0500 1.0000 Uiso R . . . . . H111 H -0.5623 0.1758 -0.5773 0.0502 1.0000 Uiso R . . . . . H271 H -0.7930 0.1423 -0.9763 0.0689 1.0000 Uiso R . . . . . H272 H -0.8887 0.2273 -0.9611 0.0692 1.0000 Uiso R . . . . . H273 H -0.6875 0.2164 -0.9245 0.0689 1.0000 Uiso R . . . . . H71 H -0.9323 0.3218 -0.8339 0.0542 1.0000 Uiso R . . . . . H72 H -1.0834 0.2982 -0.7397 0.0536 1.0000 Uiso R . . . . . H62 H -0.9899 0.4373 -0.7184 0.0580 1.0000 Uiso R . . . . . H61 H -0.9592 0.3886 -0.5984 0.0580 1.0000 Uiso R . . . . . H51 H -0.6971 0.4069 -0.7762 0.0450 1.0000 Uiso R . . . . . H12 H -0.3888 0.3751 -0.7357 0.0455 1.0000 Uiso R . . . . . H11 H -0.3330 0.3599 -0.6009 0.0462 1.0000 Uiso R . . . . . H311 H -0.1449 0.7037 -0.6902 0.1000 1.0000 Uiso R . . . . . H313 H -0.2501 0.6718 -0.8022 0.1001 1.0000 Uiso R . . . . . H312 H -0.0717 0.6283 -0.7647 0.1003 1.0000 Uiso R . . . . . H233 H -0.6391 0.6110 -0.7355 0.0891 1.0000 Uiso R . . . . . H232 H -0.8041 0.5589 -0.7790 0.0887 1.0000 Uiso R . . . . . H231 H -0.6118 0.5380 -0.8269 0.0890 1.0000 Uiso R . . . . . H243 H -0.6945 0.5882 -0.5292 0.0931 1.0000 Uiso R . . . . . H242 H -0.8699 0.5395 -0.5599 0.0927 1.0000 Uiso R . . . . . H241 H -0.7250 0.4998 -0.4748 0.0930 1.0000 Uiso R . . . . . H263 H -1.0326 0.1861 -0.5940 0.0740 1.0000 Uiso R . . . . . H262 H -0.9303 0.2574 -0.5321 0.0741 1.0000 Uiso R . . . . . H261 H -0.8408 0.1713 -0.5462 0.0740 1.0000 Uiso R . . . . . H253 H -0.5765 0.3822 -0.4513 0.0748 1.0000 Uiso R . . . . . H252 H -0.7602 0.3399 -0.4727 0.0749 1.0000 Uiso R . . . . . H251 H -0.5861 0.2859 -0.4623 0.0747 1.0000 Uiso R . . . . . H21 H -0.3034 0.4837 -0.4898 0.0739 1.0000 Uiso 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 C10 0.0399(18) 0.0330(18) 0.0315(17) -0.0009(14) -0.0009(14) 0.0033(15) C9 0.0342(17) 0.0312(17) 0.0328(17) -0.0010(14) -0.0034(13) 0.0060(14) C8 0.0322(17) 0.0388(19) 0.0325(17) -0.0043(14) -0.0006(13) 0.0037(15) C14 0.0314(16) 0.0397(19) 0.0372(18) -0.0023(16) 0.0014(13) 0.0030(15) C13 0.0384(18) 0.0319(18) 0.0383(19) 0.0012(15) -0.0053(14) -0.0008(15) C18 0.0388(19) 0.0377(19) 0.0378(18) -0.0027(16) 0.0008(15) -0.0017(16) C17 0.045(2) 0.044(2) 0.049(2) -0.0134(19) 0.0066(18) -0.0085(19) C16 0.035(2) 0.065(3) 0.069(3) -0.023(3) -0.0079(19) -0.003(2) C15 0.033(2) 0.060(3) 0.070(3) -0.020(3) -0.0030(18) 0.0034(19) C28 0.077(4) 0.065(3) 0.057(3) -0.012(3) 0.028(3) -0.021(3) O1 0.103(3) 0.060(2) 0.0403(18) 0.0040(17) 0.0135(19) -0.013(2) C19 0.063(3) 0.035(2) 0.0363(19) -0.0014(17) -0.0061(18) -0.0022(18) C20 0.075(3) 0.036(2) 0.045(2) -0.0062(19) -0.007(2) 0.006(2) C21 0.071(3) 0.043(3) 0.060(3) -0.010(2) -0.002(2) -0.006(2) C22 0.047(2) 0.056(3) 0.051(3) -0.017(2) 0.0011(18) -0.010(2) C29 0.064(3) 0.065(3) 0.061(3) -0.017(3) 0.004(2) 0.012(3) C30 0.139(7) 0.033(2) 0.074(4) -0.006(3) -0.026(4) 0.016(3) C12 0.0383(19) 0.0327(19) 0.052(2) -0.0073(17) -0.0069(16) 0.0066(15) C11 0.0400(19) 0.0352(19) 0.050(2) -0.0006(18) -0.0151(16) 0.0013(16) C27 0.053(2) 0.049(2) 0.0347(19) 0.0006(17) -0.0056(16) 0.005(2) C7 0.0345(19) 0.046(2) 0.058(3) -0.005(2) -0.0084(17) 0.0050(18) C6 0.039(2) 0.043(2) 0.062(3) -0.009(2) -0.0038(19) 0.0100(18) C5 0.042(2) 0.0321(18) 0.0418(19) -0.0030(15) 0.0015(15) 0.0077(16) C4 0.041(2) 0.037(2) 0.049(2) -0.0066(17) 0.0079(17) 0.0022(17) C3 0.0424(19) 0.0370(19) 0.042(2) -0.0069(16) 0.0015(16) 0.0007(16) C1 0.0400(19) 0.0308(17) 0.046(2) -0.0050(15) -0.0032(16) 0.0067(15) C2 0.0367(19) 0.046(2) 0.046(2) -0.0026(18) 0.0006(16) 0.0016(17) O4 0.074(2) 0.056(2) 0.0505(19) -0.0066(16) 0.0113(17) -0.0167(19) C31 0.078(4) 0.059(3) 0.060(3) 0.004(3) 0.008(3) -0.018(3) O3 0.073(2) 0.062(2) 0.052(2) -0.0083(18) 0.0154(17) -0.005(2) O2 0.0612(19) 0.0483(18) 0.0394(16) -0.0057(13) -0.0022(14) 0.0015(15) C23 0.060(3) 0.045(3) 0.074(4) 0.015(2) -0.006(3) 0.012(2) C24 0.053(3) 0.062(3) 0.070(3) -0.028(3) 0.009(2) 0.009(2) C26 0.051(2) 0.056(3) 0.040(2) -0.0019(19) 0.0120(18) -0.010(2) C25 0.067(3) 0.054(3) 0.0315(18) -0.0036(18) -0.0024(18) 0.000(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5570(19) 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 C10 . C9 . 1.544(5) yes C10 . C5 . 1.537(5) yes C10 . C1 . 1.551(6) yes C10 . C25 . 1.554(6) yes C9 . C8 . 1.572(5) yes C9 . C11 . 1.539(5) yes C9 . H91 . 0.985 no C8 . C14 . 1.595(5) yes C8 . C7 . 1.556(6) yes C8 . C26 . 1.548(6) yes C14 . C13 . 1.559(5) yes C14 . C15 . 1.555(6) yes C14 . C27 . 1.540(6) yes C13 . C18 . 1.542(5) yes C13 . C12 . 1.536(5) yes C13 . H131 . 0.980 no C18 . C17 . 1.543(6) yes C18 . C19 . 1.522(6) yes C18 . H181 . 0.984 no C17 . C16 . 1.514(7) yes C17 . C28 . 1.551(8) yes C17 . C22 . 1.541(6) yes C16 . C15 . 1.527(7) yes C16 . H161 . 0.976 no C16 . H162 . 0.966 no C15 . H151 . 0.972 no C15 . H152 . 0.973 no C28 . O1 . 1.432(9) yes C28 . H282 . 0.979 no C28 . H281 . 0.970 no O1 . C19 . 1.456(6) yes C19 . C20 . 1.534(6) yes C19 . H191 . 0.989 no C20 . C21 . 1.548(8) yes C20 . C29 . 1.541(8) yes C20 . C30 . 1.532(7) yes C21 . C22 . 1.527(8) yes C21 . H212 . 0.970 no C21 . H211 . 0.976 no C22 . H221 . 0.972 no C22 . H222 . 0.976 no C29 . H291 . 0.959 no C29 . H292 . 0.972 no C29 . H293 . 0.964 no C30 . H301 . 0.966 no C30 . H302 . 0.968 no C30 . H303 . 0.968 no C12 . C11 . 1.530(6) yes C12 . H121 . 0.973 no C12 . H122 . 0.969 no C11 . H112 . 0.962 no C11 . H111 . 0.974 no C27 . H271 . 0.961 no C27 . H272 . 0.959 no C27 . H273 . 0.954 no C7 . C6 . 1.547(7) yes C7 . H71 . 0.969 no C7 . H72 . 0.973 no C6 . C5 . 1.520(6) yes C6 . H62 . 0.964 no C6 . H61 . 0.972 no C5 . C4 . 1.549(6) yes C5 . H51 . 0.984 no C4 . C3 . 1.606(6) yes C4 . C23 . 1.535(7) yes C4 . C24 . 1.537(6) yes C3 . C1 . 1.555(6) yes C3 . C2 . 1.535(6) yes C3 . O2 . 1.437(5) yes C1 . H12 . 0.973 no C1 . H11 . 0.966 no C2 . O4 . 1.338(6) yes C2 . O3 . 1.192(6) yes O4 . C31 . 1.453(6) yes C31 . H311 . 0.963 no C31 . H313 . 0.963 no C31 . H312 . 0.962 no O2 . H21 . 0.820 no C23 . H233 . 0.970 no C23 . H232 . 0.961 no C23 . H231 . 0.958 no C24 . H243 . 0.958 no C24 . H242 . 0.968 no C24 . H241 . 0.964 no C26 . H263 . 0.945 no C26 . H262 . 0.954 no C26 . H261 . 0.962 no C25 . H253 . 0.961 no C25 . H252 . 0.956 no C25 . H251 . 0.970 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 C9 . C10 . C5 . 106.5(3) yes C9 . C10 . C1 . 113.3(3) yes C5 . C10 . C1 . 98.5(3) yes C9 . C10 . C25 . 113.8(4) yes C5 . C10 . C25 . 115.5(4) yes C1 . C10 . C25 . 108.2(4) yes C10 . C9 . C8 . 114.7(3) yes C10 . C9 . C11 . 114.4(3) yes C8 . C9 . C11 . 110.5(3) yes C10 . C9 . H91 . 104.5 no C8 . C9 . H91 . 104.9 no C11 . C9 . H91 . 106.8 no C9 . C8 . C14 . 108.0(3) yes C9 . C8 . C7 . 109.1(3) yes C14 . C8 . C7 . 109.8(3) yes C9 . C8 . C26 . 112.2(3) yes C14 . C8 . C26 . 110.1(4) yes C7 . C8 . C26 . 107.5(4) yes C8 . C14 . C13 . 108.3(3) yes C8 . C14 . C15 . 110.5(3) yes C13 . C14 . C15 . 108.1(4) yes C8 . C14 . C27 . 112.3(4) yes C13 . C14 . C27 . 110.5(3) yes C15 . C14 . C27 . 107.0(4) yes C14 . C13 . C18 . 112.3(3) yes C14 . C13 . C12 . 111.0(3) yes C18 . C13 . C12 . 111.2(3) yes C14 . C13 . H131 . 107.2 no C18 . C13 . H131 . 107.5 no C12 . C13 . H131 . 107.3 no C13 . C18 . C17 . 113.6(3) yes C13 . C18 . C19 . 113.0(3) yes C17 . C18 . C19 . 99.2(4) yes C13 . C18 . H181 . 110.0 no C17 . C18 . H181 . 110.6 no C19 . C18 . H181 . 110.0 no C18 . C17 . C16 . 113.2(4) yes C18 . C17 . C28 . 99.1(4) yes C16 . C17 . C28 . 115.4(5) yes C18 . C17 . C22 . 107.8(4) yes C16 . C17 . C22 . 110.7(4) yes C28 . C17 . C22 . 110.0(4) yes C17 . C16 . C15 . 113.6(4) yes C17 . C16 . H161 . 108.0 no C15 . C16 . H161 . 108.2 no C17 . C16 . H162 . 108.7 no C15 . C16 . H162 . 108.2 no H161 . C16 . H162 . 110.0 no C16 . C15 . C14 . 113.4(4) yes C16 . C15 . H151 . 109.0 no C14 . C15 . H151 . 108.8 no C16 . C15 . H152 . 108.3 no C14 . C15 . H152 . 108.4 no H151 . C15 . H152 . 108.9 no C17 . C28 . O1 . 107.1(4) yes C17 . C28 . H282 . 110.3 no O1 . C28 . H282 . 111.3 no C17 . C28 . H281 . 109.9 no O1 . C28 . H281 . 109.5 no H282 . C28 . H281 . 108.8 no C28 . O1 . C19 . 107.8(4) yes C18 . C19 . O1 . 103.2(4) yes C18 . C19 . C20 . 113.8(4) yes O1 . C19 . C20 . 109.5(4) yes C18 . C19 . H191 . 110.9 no O1 . C19 . H191 . 109.4 no C20 . C19 . H191 . 109.8 no C19 . C20 . C21 . 108.5(4) yes C19 . C20 . C29 . 109.3(4) yes C21 . C20 . C29 . 111.5(5) yes C19 . C20 . C30 . 110.2(4) yes C21 . C20 . C30 . 108.9(5) yes C29 . C20 . C30 . 108.4(5) yes C20 . C21 . C22 . 113.1(4) yes C20 . C21 . H212 . 108.6 no C22 . C21 . H212 . 108.8 no C20 . C21 . H211 . 108.4 no C22 . C21 . H211 . 108.9 no H212 . C21 . H211 . 109.0 no C17 . C22 . C21 . 112.7(4) yes C17 . C22 . H221 . 107.9 no C21 . C22 . H221 . 108.1 no C17 . C22 . H222 . 108.4 no C21 . C22 . H222 . 109.9 no H221 . C22 . H222 . 109.8 no C20 . C29 . H291 . 110.4 no C20 . C29 . H292 . 110.3 no H291 . C29 . H292 . 108.6 no C20 . C29 . H293 . 109.4 no H291 . C29 . H293 . 108.9 no H292 . C29 . H293 . 109.2 no C20 . C30 . H301 . 110.4 no C20 . C30 . H302 . 110.0 no H301 . C30 . H302 . 108.5 no C20 . C30 . H303 . 110.5 no H301 . C30 . H303 . 108.5 no H302 . C30 . H303 . 108.9 no C13 . C12 . C11 . 111.2(3) yes C13 . C12 . H121 . 108.7 no C11 . C12 . H121 . 110.3 no C13 . C12 . H122 . 107.8 no C11 . C12 . H122 . 109.4 no H121 . C12 . H122 . 109.4 no C9 . C11 . C12 . 111.3(3) yes C9 . C11 . H112 . 109.0 no C12 . C11 . H112 . 109.2 no C9 . C11 . H111 . 108.6 no C12 . C11 . H111 . 109.4 no H112 . C11 . H111 . 109.3 no C14 . C27 . H271 . 108.3 no C14 . C27 . H272 . 110.4 no H271 . C27 . H272 . 109.5 no C14 . C27 . H273 . 109.7 no H271 . C27 . H273 . 108.4 no H272 . C27 . H273 . 110.4 no C8 . C7 . C6 . 114.7(4) yes C8 . C7 . H71 . 108.8 no C6 . C7 . H71 . 107.5 no C8 . C7 . H72 . 108.2 no C6 . C7 . H72 . 107.6 no H71 . C7 . H72 . 110.1 no C7 . C6 . C5 . 107.6(4) yes C7 . C6 . H62 . 109.9 no C5 . C6 . H62 . 109.6 no C7 . C6 . H61 . 110.8 no C5 . C6 . H61 . 110.2 no H62 . C6 . H61 . 108.7 no C10 . C5 . C6 . 112.4(4) yes C10 . C5 . C4 . 108.6(3) yes C6 . C5 . C4 . 120.3(3) yes C10 . C5 . H51 . 105.3 no C6 . C5 . H51 . 104.4 no C4 . C5 . H51 . 104.5 no C5 . C4 . C3 . 101.5(3) yes C5 . C4 . C23 . 108.8(4) yes C3 . C4 . C23 . 113.7(4) yes C5 . C4 . C24 . 114.2(4) yes C3 . C4 . C24 . 111.2(4) yes C23 . C4 . C24 . 107.6(4) yes C4 . C3 . C1 . 105.9(3) yes C4 . C3 . C2 . 109.5(4) yes C1 . C3 . C2 . 111.3(4) yes C4 . C3 . O2 . 109.0(3) yes C1 . C3 . O2 . 112.8(4) yes C2 . C3 . O2 . 108.2(3) yes C10 . C1 . C3 . 105.1(3) yes C10 . C1 . H12 . 110.4 no C3 . C1 . H12 . 109.6 no C10 . C1 . H11 . 111.9 no C3 . C1 . H11 . 110.7 no H12 . C1 . H11 . 109.1 no C3 . C2 . O4 . 112.3(4) yes C3 . C2 . O3 . 125.0(4) yes O4 . C2 . O3 . 122.7(5) yes C2 . O4 . C31 . 116.1(4) yes O4 . C31 . H311 . 109.8 no O4 . C31 . H313 . 108.6 no H311 . C31 . H313 . 108.7 no O4 . C31 . H312 . 110.2 no H311 . C31 . H312 . 110.3 no H313 . C31 . H312 . 109.1 no C3 . O2 . H21 . 108.8 no C4 . C23 . H233 . 108.9 no C4 . C23 . H232 . 109.2 no H233 . C23 . H232 . 109.4 no C4 . C23 . H231 . 109.3 no H233 . C23 . H231 . 110.0 no H232 . C23 . H231 . 110.1 no C4 . C24 . H243 . 108.9 no C4 . C24 . H242 . 108.5 no H243 . C24 . H242 . 109.4 no C4 . C24 . H241 . 109.9 no H243 . C24 . H241 . 110.4 no H242 . C24 . H241 . 109.7 no C8 . C26 . H263 . 109.5 no C8 . C26 . H262 . 109.4 no H263 . C26 . H262 . 109.6 no C8 . C26 . H261 . 110.4 no H263 . C26 . H261 . 108.8 no H262 . C26 . H261 . 109.1 no C10 . C25 . H253 . 109.5 no C10 . C25 . H252 . 109.1 no H253 . C25 . H252 . 108.5 no C10 . C25 . H251 . 110.7 no H253 . C25 . H251 . 109.1 no H252 . C25 . H251 . 109.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C22 . H222 . O3 2_443 169.08 0.976 2.528 3.492(7) yes C23 . H231 . O3 . 120.90 0.958 2.504 3.107(7) yes C25 . H253 . O2 . 137.73 0.961 2.361 3.140(7) yes O2 . H21 . O1 2_454 130.73 0.820 2.419 3.019(7) yes _iucr_refine_instruction_details_constraints ; # # Punched on 19/06/13 at 14:59:41 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 28,X'S) H ( 282,X'S) H ( 281,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) RIDE C ( 29,X'S) H ( 291,X'S) H ( 292,X'S) H ( 293,X'S) RIDE C ( 30,X'S) H ( 301,X'S) H ( 302,X'S) H ( 303,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) H ( 273,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) RIDE C ( 6,X'S) H ( 62,X'S) H ( 61,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 1,X'S) H ( 12,X'S) H ( 11,X'S) RIDE C ( 31,X'S) H ( 311,X'S) H ( 313,X'S) H ( 312,X'S) RIDE O ( 2,X'S) H ( 21,X'S) RIDE C ( 23,X'S) H ( 233,X'S) H ( 232,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 243,X'S) H ( 242,X'S) H ( 241,X'S) RIDE C ( 26,X'S) H ( 263,X'S) H ( 262,X'S) H ( 261,X'S) RIDE C ( 25,X'S) H ( 253,X'S) H ( 252,X'S) H ( 251,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 19/06/13 at 14:59:41 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -4 0 9 x . -5 0 8 x . 4 0 10 x . -3 10 7 x . _database_code_depnum_ccdc_archive 'CCDC 721850'