# Electronic Supplementary Material (ESI) for Chemical Communications # 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 7.5396(3) _cell_length_b 33.1120(9) _cell_length_c 7.9405(6) _cell_angle_alpha 90 _cell_angle_beta 91.215(6) _cell_angle_gamma 90 _cell_volume 1981.92(17) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 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 I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 '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' 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' _cell_formula_units_Z 4 # Given Formula = C17 H11 I1 O6 S1 # Dc = 1.58 Fooo = 1064.00 Mu = 17.48 M = 470.24 # Found Formula = C18 H17 I1 O9 S1 # Dc = 1.80 FOOO = 1064.00 Mu = 17.70 M = 536.30 _chemical_formula_sum 'C18 H17 I1 O9 S1' _chemical_formula_moiety 'C18 H17 I1 O9 S1' _chemical_compound_source ? _chemical_formula_weight 536.30 _cell_measurement_reflns_used 4530 _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.210 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_max 0.310 _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.770 # Sheldrick geometric approximatio 0.64 0.69 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 0.69 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_method \w # 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 'SHELXS 86 (Sheldrick, 1986)' _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 2 _diffrn_standards_interval_count . _diffrn_standards_number 4530 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 123 _diffrn_reflns_number 14171 _reflns_number_total 4530 _diffrn_reflns_av_R_equivalents 0.035 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 4530 # Theoretical number of reflections is about 9090 _diffrn_reflns_theta_min 3.161 _diffrn_reflns_theta_max 27.483 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.483 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 42 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.75 _refine_diff_density_max 1.11 # 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>0.0\s(I) _refine_ls_number_reflns 4517 _refine_ls_number_restraints 0 _refine_ls_number_parameters 262 _oxford_refine_ls_R_factor_ref 0.0419 _refine_ls_wR_factor_ref 0.0596 _refine_ls_goodness_of_fit_ref 0.9685 _refine_ls_shift/su_max 0.0051300 _refine_ls_shift/su_mean 0.0001094 # The values computed with all filters except I/sigma _oxford_reflns_number_all 4517 _refine_ls_R_factor_all 0.0419 _refine_ls_wR_factor_all 0.0596 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3658 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_gt 0.0549 # 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 . _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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 5.35P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 I1 I 0.30726(2) 0.648259(5) 0.86709(2) 0.0154 1.0000 Uani . . . . . . O8 O 0.2168(3) 0.65714(6) 1.0988(3) 0.0190 1.0000 Uani . . . . . . C17 C 0.0506(4) 0.64170(9) 1.1156(4) 0.0222 1.0000 Uani . . . . . . O9 O -0.0278(3) 0.62723(7) 0.9963(3) 0.0294 1.0000 Uani . . . . . . C18 C -0.0124(4) 0.64552(12) 1.2915(4) 0.0297 1.0000 Uani . . . . . . O1 O 0.1307(3) 0.69121(6) 0.7716(3) 0.0240 1.0000 Uani . . . . . . C7 C 0.1855(4) 0.72975(10) 0.7806(4) 0.0241 1.0000 Uani . . . . . . O2 O 0.0952(3) 0.75723(7) 0.7277(4) 0.0362 1.0000 Uani . . . . . . C6 C 0.3659(4) 0.73447(9) 0.8574(4) 0.0183 1.0000 Uani . . . . . . C1 C 0.4583(4) 0.70052(9) 0.9081(4) 0.0163 1.0000 Uani . . . . . . C2 C 0.6286(4) 0.70069(10) 0.9741(4) 0.0218 1.0000 Uani . . . . . . C3 C 0.7076(4) 0.73857(10) 0.9939(4) 0.0242 1.0000 Uani . . . . . . C4 C 0.6177(4) 0.77341(10) 0.9473(4) 0.0248 1.0000 Uani . . . . . . C5 C 0.4474(4) 0.77176(9) 0.8772(4) 0.0228 1.0000 Uani . . . . . . O6 O 0.5136(3) 0.61877(6) 0.9792(3) 0.0186 1.0000 Uani . . . . . . C15 C 0.4686(4) 0.58047(9) 1.0171(4) 0.0218 1.0000 Uani . . . . . . O7 O 0.3184(3) 0.56855(7) 0.9956(3) 0.0323 1.0000 Uani . . . . . . C16 C 0.6216(4) 0.55647(10) 1.0838(4) 0.0256 1.0000 Uani . . . . . . O3 O 0.4798(3) 0.64745(6) 0.6451(3) 0.0199 1.0000 Uani . . . . . . S1 S 0.46965(10) 0.61138(2) 0.52580(10) 0.0196 1.0000 Uani . . . . . . O4 O 0.5273(3) 0.62448(7) 0.3634(3) 0.0297 1.0000 Uani . . . . . . O5 O 0.2968(3) 0.59317(7) 0.5354(3) 0.0290 1.0000 Uani . . . . . . C8 C 0.6260(4) 0.57663(9) 0.6067(4) 0.0187 1.0000 Uani . . . . . . C13 C 0.5773(4) 0.53667(10) 0.6304(4) 0.0241 1.0000 Uani . . . . . . C12 C 0.7040(5) 0.50880(10) 0.6818(5) 0.0287 1.0000 Uani . . . . . . C9 C 0.7999(4) 0.58881(10) 0.6407(4) 0.0251 1.0000 Uani . . . . . . C10 C 0.9237(4) 0.56051(11) 0.6931(5) 0.0292 1.0000 Uani . . . . . . C11 C 0.8777(4) 0.52001(11) 0.7110(4) 0.0259 1.0000 Uani . . . . . . C14 C 1.0160(5) 0.48944(12) 0.7653(5) 0.0383 1.0000 Uani . . . . . . H181 H -0.1341 0.6378 1.2897 0.0448 1.0000 Uiso R . . . . . H182 H 0.0015 0.6730 1.3257 0.0452 1.0000 Uiso R . . . . . H183 H 0.0568 0.6285 1.3634 0.0452 1.0000 Uiso R . . . . . H21 H 0.6868 0.6767 1.0032 0.0277 1.0000 Uiso R . . . . . H31 H 0.8224 0.7404 1.0425 0.0302 1.0000 Uiso R . . . . . H41 H 0.6712 0.7982 0.9639 0.0303 1.0000 Uiso R . . . . . H51 H 0.3876 0.7952 0.8458 0.0293 1.0000 Uiso R . . . . . H161 H 0.5938 0.5281 1.0747 0.0392 1.0000 Uiso R . . . . . H162 H 0.6446 0.5635 1.1977 0.0394 1.0000 Uiso R . . . . . H163 H 0.7241 0.5625 1.0213 0.0394 1.0000 Uiso R . . . . . H131 H 0.4611 0.5286 0.6092 0.0291 1.0000 Uiso R . . . . . H121 H 0.6711 0.4820 0.6966 0.0353 1.0000 Uiso R . . . . . H91 H 0.8319 0.6161 0.6272 0.0309 1.0000 Uiso R . . . . . H101 H 1.0393 0.5688 0.7204 0.0361 1.0000 Uiso R . . . . . H141 H 1.1096 0.5017 0.8314 0.0591 1.0000 Uiso R . . . . . H142 H 0.9639 0.4686 0.8307 0.0593 1.0000 Uiso R . . . . . H143 H 1.0664 0.4775 0.6690 0.0595 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 I1 0.01390(8) 0.01505(9) 0.01723(9) -0.00027(8) -0.00064(6) 0.00052(8) O8 0.0167(10) 0.0229(11) 0.0175(11) -0.0016(8) 0.0032(8) -0.0019(8) C17 0.0152(14) 0.0230(16) 0.0284(17) 0.0030(14) 0.0019(12) 0.0018(12) O9 0.0192(11) 0.0376(14) 0.0314(13) -0.0026(11) -0.0005(10) -0.0052(10) C18 0.0229(15) 0.040(2) 0.0267(17) 0.0039(16) 0.0067(13) -0.0019(16) O1 0.0189(11) 0.0188(11) 0.0341(13) 0.0039(10) -0.0068(10) 0.0000(9) C7 0.0221(16) 0.0238(16) 0.0264(17) 0.0045(14) -0.0010(13) 0.0014(13) O2 0.0250(13) 0.0247(12) 0.0584(18) 0.0104(12) -0.0128(12) 0.0039(10) C6 0.0167(14) 0.0174(14) 0.0209(15) 0.0002(12) 0.0016(12) 0.0000(11) C1 0.0183(14) 0.0150(13) 0.0156(14) -0.0031(12) 0.0014(11) -0.0029(11) C2 0.0184(15) 0.0218(15) 0.0252(16) 0.0003(13) -0.0005(13) 0.0025(12) C3 0.0173(15) 0.0259(16) 0.0292(17) -0.0030(14) -0.0011(13) -0.0039(13) C4 0.0240(16) 0.0210(15) 0.0296(17) -0.0057(14) 0.0041(14) -0.0063(13) C5 0.0229(16) 0.0171(14) 0.0286(17) 0.0004(13) 0.0031(13) 0.0003(13) O6 0.0169(10) 0.0176(10) 0.0213(11) 0.0045(9) 0.0007(8) 0.0025(8) C15 0.0246(16) 0.0197(15) 0.0211(16) 0.0033(13) 0.0026(13) 0.0046(13) O7 0.0244(12) 0.0264(12) 0.0460(16) 0.0088(12) -0.0050(11) -0.0036(10) C16 0.0266(17) 0.0267(17) 0.0235(16) 0.0020(14) -0.0006(13) 0.0093(14) O3 0.0255(11) 0.0169(10) 0.0176(10) -0.0021(9) 0.0053(8) -0.0004(9) S1 0.0220(4) 0.0196(4) 0.0173(4) -0.0018(3) -0.0009(3) 0.0020(3) O4 0.0409(14) 0.0327(13) 0.0157(11) 0.0004(10) 0.0022(10) 0.0078(11) O5 0.0227(12) 0.0256(12) 0.0385(14) -0.0034(11) -0.0057(10) 0.0008(10) C8 0.0195(14) 0.0203(15) 0.0164(14) -0.0002(12) 0.0004(12) 0.0033(12) C13 0.0203(15) 0.0200(15) 0.0320(18) -0.0021(14) -0.0015(13) -0.0030(13) C12 0.0329(18) 0.0194(15) 0.0338(19) 0.0011(14) -0.0027(16) -0.0005(14) C9 0.0238(16) 0.0250(16) 0.0266(17) 0.0025(14) 0.0034(14) -0.0012(13) C10 0.0184(15) 0.0345(19) 0.0345(19) -0.0016(16) 0.0005(14) 0.0007(14) C11 0.0265(17) 0.0324(18) 0.0189(15) -0.0003(14) 0.0032(13) 0.0107(15) C14 0.035(2) 0.042(2) 0.038(2) 0.0018(18) -0.0012(17) 0.0168(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4971(4) 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 I1 . O8 . 1.998(2) yes I1 . O1 . 2.080(2) yes I1 . C1 . 2.093(3) yes I1 . O6 . 2.027(2) yes I1 . O3 . 2.213(2) yes O8 . C17 . 1.362(4) yes C17 . O9 . 1.205(4) yes C17 . C18 . 1.491(4) yes C18 . H181 . 0.952 no C18 . H182 . 0.955 no C18 . H183 . 0.952 no O1 . C7 . 1.343(4) yes C7 . O2 . 1.207(4) yes C7 . C6 . 1.487(4) yes C6 . C1 . 1.378(4) yes C6 . C5 . 1.387(4) yes C1 . C2 . 1.376(4) yes C2 . C3 . 1.396(4) yes C2 . H21 . 0.934 no C3 . C4 . 1.384(5) yes C3 . H31 . 0.942 no C4 . C5 . 1.390(5) yes C4 . H41 . 0.923 no C5 . H51 . 0.930 no O6 . C15 . 1.348(4) yes C15 . O7 . 1.208(4) yes C15 . C16 . 1.488(4) yes C16 . H161 . 0.965 no C16 . H162 . 0.946 no C16 . H163 . 0.948 no O3 . S1 . 1.525(2) yes S1 . O4 . 1.437(2) yes S1 . O5 . 1.440(2) yes S1 . C8 . 1.759(3) yes C8 . C13 . 1.387(4) yes C8 . C9 . 1.393(4) yes C13 . C12 . 1.384(5) yes C13 . H131 . 0.928 no C12 . C11 . 1.376(5) yes C12 . H121 . 0.929 no C9 . C10 . 1.380(5) yes C9 . H91 . 0.941 no C10 . C11 . 1.393(5) yes C10 . H101 . 0.935 no C11 . C14 . 1.509(5) yes C14 . H141 . 0.961 no C14 . H142 . 0.954 no C14 . H143 . 0.948 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 O8 . I1 . O1 . 90.39(9) yes O8 . I1 . C1 . 85.99(10) yes O1 . I1 . C1 . 80.41(10) yes O8 . I1 . O6 . 86.57(8) yes O1 . I1 . O6 . 165.67(8) yes C1 . I1 . O6 . 85.41(10) yes O8 . I1 . O3 . 162.44(8) yes O1 . I1 . O3 . 95.75(9) yes C1 . I1 . O3 . 78.87(10) yes O6 . I1 . O3 . 83.42(8) yes I1 . O8 . C17 . 111.54(19) yes O8 . C17 . O9 . 120.6(3) yes O8 . C17 . C18 . 111.8(3) yes O9 . C17 . C18 . 127.5(3) yes C17 . C18 . H181 . 106.8 no C17 . C18 . H182 . 108.2 no H181 . C18 . H182 . 111.0 no C17 . C18 . H183 . 109.3 no H181 . C18 . H183 . 111.5 no H182 . C18 . H183 . 109.9 no I1 . O1 . C7 . 115.87(19) yes O1 . C7 . O2 . 121.8(3) yes O1 . C7 . C6 . 113.6(3) yes O2 . C7 . C6 . 124.6(3) yes C7 . C6 . C1 . 119.1(3) yes C7 . C6 . C5 . 122.6(3) yes C1 . C6 . C5 . 118.3(3) yes C6 . C1 . I1 . 111.0(2) yes C6 . C1 . C2 . 124.7(3) yes I1 . C1 . C2 . 124.2(2) yes C1 . C2 . C3 . 116.1(3) yes C1 . C2 . H21 . 121.4 no C3 . C2 . H21 . 122.6 no C2 . C3 . C4 . 120.9(3) yes C2 . C3 . H31 . 119.3 no C4 . C3 . H31 . 119.8 no C3 . C4 . C5 . 121.2(3) yes C3 . C4 . H41 . 119.5 no C5 . C4 . H41 . 119.3 no C4 . C5 . C6 . 118.9(3) yes C4 . C5 . H51 . 120.9 no C6 . C5 . H51 . 120.2 no I1 . O6 . C15 . 110.92(18) yes O6 . C15 . O7 . 121.0(3) yes O6 . C15 . C16 . 112.6(3) yes O7 . C15 . C16 . 126.4(3) yes C15 . C16 . H161 . 109.1 no C15 . C16 . H162 . 109.5 no H161 . C16 . H162 . 110.2 no C15 . C16 . H163 . 109.6 no H161 . C16 . H163 . 110.1 no H162 . C16 . H163 . 108.3 no I1 . O3 . S1 . 118.78(12) yes O3 . S1 . O4 . 107.99(13) yes O3 . S1 . O5 . 109.19(13) yes O4 . S1 . O5 . 117.75(15) yes O3 . S1 . C8 . 105.13(13) yes O4 . S1 . C8 . 108.20(14) yes O5 . S1 . C8 . 107.88(15) yes S1 . C8 . C13 . 119.7(2) yes S1 . C8 . C9 . 120.1(2) yes C13 . C8 . C9 . 120.1(3) yes C8 . C13 . C12 . 119.5(3) yes C8 . C13 . H131 . 120.1 no C12 . C13 . H131 . 120.4 no C13 . C12 . C11 . 121.2(3) yes C13 . C12 . H121 . 119.3 no C11 . C12 . H121 . 119.5 no C8 . C9 . C10 . 119.3(3) yes C8 . C9 . H91 . 119.9 no C10 . C9 . H91 . 120.8 no C9 . C10 . C11 . 121.1(3) yes C9 . C10 . H101 . 119.4 no C11 . C10 . H101 . 119.5 no C10 . C11 . C12 . 118.7(3) yes C10 . C11 . C14 . 120.2(3) yes C12 . C11 . C14 . 121.1(3) yes C11 . C14 . H141 . 111.5 no C11 . C14 . H142 . 110.6 no H141 . C14 . H142 . 108.4 no C11 . C14 . H143 . 109.6 no H141 . C14 . H143 . 108.3 no H142 . C14 . H143 . 108.3 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 C18 . H182 . O2 4_565 143.93(10) 0.955 2.542 3.362(5) yes C18 . H183 . O5 1_556 167.26(9) 0.952 2.530 3.464(5) yes C3 . H31 . O2 4_665 168.11(10) 0.942 2.504 3.432(5) yes C16 . H162 . O4 1_556 128.53(9) 0.946 2.577 3.252(5) yes C10 . H101 . O5 1_655 131.84(10) 0.935 2.588 3.286(5) yes _iucr_refine_instruction_details_constraints ; # # Punched on 29/08/13 at 16:54:28 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) H ( 183,X'S) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) H ( 163,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 29/08/13 at 16:54:28 # #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 0 0 6 x . -2 0 10 x . 1 40 3 x . _database_code_depnum_ccdc_archive 'CCDC 959250'