# 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_9 _database_code_depnum_ccdc_archive 'CCDC 904095' #TrackingRef '14397_web_deposit_cif_file_0_AmberL.Thompson_1349225863.CrystallographicData.cif' #============================================================================== _audit_creation_date 2012-09-26 _audit_creation_method CRYSTALS_ver_14.52 _oxford_structure_analysis_title 6455 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 10.5479(1) _cell_length_b 12.7584(1) _cell_length_c 19.3047(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2597.92(4) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,-y,z+1/2 x+1/2,-y+1/2,-z -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 C 0.0181 0.0091 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' S 0.3331 0.5567 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 0.0492 0.0322 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' Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C27.50 H25 Cl1 O5 S2.50 # Dc = 1.41 Fooo = 1064.00 Mu = 34.91 M = 551.12 # Found Formula = C31 H39 Cl1 O3 # Dc = 1.27 FOOO = 1064.00 Mu = 15.34 M = 495.10 _chemical_formula_sum 'C31 H39 Cl1 O3' _chemical_formula_moiety 'C31 H39 Cl1 O3' _chemical_compound_source . _chemical_formula_weight 495.10 _cell_measurement_reflns_used 34472 _cell_measurement_theta_min 3 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_max 0.160 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.534 # Sheldrick geometric approximatio 0.91 0.91 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.91 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 58125 _reflns_number_total 5419 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections without Friedels Law is 5419 # Number of reflections with Friedels Law is 3063 # Theoretical number of reflections is about 2733 _diffrn_reflns_theta_min 4.153 _diffrn_reflns_theta_max 76.592 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 75.061 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.74 _oxford_diffrn_Wilson_scale 0.05 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.34 _refine_diff_density_max 0.27 # 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>-3.0\s(I) _refine_ls_number_reflns 5398 _refine_ls_number_restraints 0 _refine_ls_number_parameters 317 _oxford_refine_ls_R_factor_ref 0.0278 _refine_ls_wR_factor_ref 0.0752 _refine_ls_goodness_of_fit_ref 0.9999 _refine_ls_shift/su_max 0.0006434 _refine_ls_shift/su_mean 0.0000633 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5398 _refine_ls_R_factor_all 0.0278 _refine_ls_wR_factor_all 0.0752 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5316 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_gt 0.0748 _refine_ls_abs_structure_Flack -0.011(11) _refine_ls_abs_structure_details 'Flack (1983), 2356 Friedel-pairs' # 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 ad _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^) + ( 0.05P)^2^ + 0.48P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order 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 Cl1 Cl 0.31713(5) 0.13379(3) 0.34159(3) 0.0685 1.0000 Uani . . . . . . O1 O 0.70492(9) 1.03865(8) 0.30015(5) 0.0365 1.0000 Uani . . . . . . O2 O 0.53367(10) 0.65648(7) 0.79770(5) 0.0357 1.0000 Uani . . . . . . O3 O 0.60544(15) 0.71426(10) 0.89874(6) 0.0618 1.0000 Uani . . . . . . C1 C 0.66835(11) 1.01221(9) 0.48515(6) 0.0266 1.0000 Uani . . . . . . C2 C 0.66549(13) 1.07826(10) 0.41923(6) 0.0300 1.0000 Uani . . . . . . C3 C 0.65975(11) 1.01065(10) 0.35555(6) 0.0274 1.0000 Uani . . . . . . C4 C 0.59263(11) 0.91029(10) 0.36217(6) 0.0266 1.0000 Uani . . . . . . C5 C 0.54228(10) 0.87566(9) 0.42180(6) 0.0223 1.0000 Uani . . . . . . C6 C 0.46027(11) 0.77904(9) 0.42329(6) 0.0242 1.0000 Uani . . . . . . C7 C 0.50410(10) 0.69943(9) 0.47753(6) 0.0212 1.0000 Uani . . . . . . C8 C 0.50570(10) 0.75399(9) 0.54887(6) 0.0199 1.0000 Uani . . . . . . C9 C 0.58975(10) 0.85346(8) 0.54924(6) 0.0197 1.0000 Uani . . . . . . C10 C 0.55860(10) 0.93328(9) 0.49022(6) 0.0214 1.0000 Uani . . . . . . C11 C 0.58940(12) 0.90628(9) 0.62102(6) 0.0255 1.0000 Uani . . . . . . C12 C 0.62652(11) 0.83121(9) 0.67954(6) 0.0243 1.0000 Uani . . . . . . C13 C 0.54047(11) 0.73482(9) 0.67988(6) 0.0223 1.0000 Uani . . . . . . C14 C 0.54798(10) 0.68219(8) 0.60803(6) 0.0205 1.0000 Uani . . . . . . C15 C 0.47849(12) 0.57776(9) 0.61845(6) 0.0285 1.0000 Uani . . . . . . C16 C 0.51113(13) 0.54643(10) 0.69399(7) 0.0316 1.0000 Uani . . . . . . C17 C 0.57994(12) 0.64102(9) 0.72650(6) 0.0261 1.0000 Uani . . . . . . C18 C 0.40410(12) 0.76662(11) 0.69924(7) 0.0308 1.0000 Uani . . . . . . C19 C 0.43332(11) 0.99237(10) 0.50470(7) 0.0293 1.0000 Uani . . . . . . C20 C 0.72306(13) 0.62615(10) 0.73750(7) 0.0312 1.0000 Uani . . . . . . C21 C 0.75163(15) 0.69100(11) 0.80193(7) 0.0386 1.0000 Uani . . . . . . C22 C 0.62737(17) 0.69016(10) 0.83968(7) 0.0408 1.0000 Uani . . . . . . C23 C 0.63142(11) 0.64984(9) 0.45766(6) 0.0241 1.0000 Uani . . . . . . C24 C 0.62821(11) 0.58298(10) 0.39145(6) 0.0268 1.0000 Uani . . . . . . C25 C 0.53435(11) 0.49366(9) 0.39397(6) 0.0251 1.0000 Uani . . . . . . C26 C 0.54044(13) 0.41782(10) 0.44570(6) 0.0292 1.0000 Uani . . . . . . C27 C 0.45460(14) 0.33543(10) 0.44776(7) 0.0327 1.0000 Uani . . . . . . C28 C 0.36132(13) 0.32690(10) 0.39703(8) 0.0345 1.0000 Uani . . . . . . C29 C 0.35543(13) 0.40153(11) 0.34490(7) 0.0343 1.0000 Uani . . . . . . C30 C 0.44029(12) 0.48421(10) 0.34365(7) 0.0289 1.0000 Uani . . . . . . C31 C 0.26854(17) 0.23814(13) 0.39862(12) 0.0548 1.0000 Uani . . . . . . H11 H 0.7488 0.9724 0.4859 0.0300 1.0000 Uiso R . . . . . H12 H 0.6648 1.0590 0.5269 0.0319 1.0000 Uiso R . . . . . H21 H 0.5895 1.1221 0.4170 0.0368 1.0000 Uiso R . . . . . H22 H 0.7390 1.1223 0.4163 0.0342 1.0000 Uiso R . . . . . H41 H 0.5820 0.8729 0.3216 0.0331 1.0000 Uiso R . . . . . H61 H 0.4595 0.7480 0.3767 0.0289 1.0000 Uiso R . . . . . H62 H 0.3729 0.8000 0.4344 0.0289 1.0000 Uiso R . . . . . H71 H 0.4425 0.6421 0.4794 0.0248 1.0000 Uiso R . . . . . H81 H 0.4170 0.7762 0.5588 0.0234 1.0000 Uiso R . . . . . H91 H 0.6767 0.8302 0.5398 0.0237 1.0000 Uiso R . . . . . H111 H 0.5051 0.9321 0.6303 0.0305 1.0000 Uiso R . . . . . H112 H 0.6485 0.9648 0.6218 0.0314 1.0000 Uiso R . . . . . H121 H 0.7153 0.8094 0.6731 0.0276 1.0000 Uiso R . . . . . H122 H 0.6204 0.8682 0.7234 0.0282 1.0000 Uiso R . . . . . H141 H 0.6370 0.6680 0.5996 0.0242 1.0000 Uiso R . . . . . H151 H 0.5095 0.5270 0.5861 0.0338 1.0000 Uiso R . . . . . H152 H 0.3854 0.5891 0.6115 0.0350 1.0000 Uiso R . . . . . H161 H 0.4363 0.5307 0.7193 0.0369 1.0000 Uiso R . . . . . H162 H 0.5639 0.4838 0.6951 0.0374 1.0000 Uiso R . . . . . H181 H 0.3484 0.7063 0.7028 0.0467 1.0000 Uiso R . . . . . H182 H 0.3652 0.8171 0.6652 0.0450 1.0000 Uiso R . . . . . H183 H 0.4039 0.7992 0.7451 0.0445 1.0000 Uiso R . . . . . H191 H 0.3647 0.9448 0.5180 0.0437 1.0000 Uiso R . . . . . H192 H 0.4062 1.0298 0.4622 0.0438 1.0000 Uiso R . . . . . H193 H 0.4443 1.0414 0.5427 0.0433 1.0000 Uiso R . . . . . H201 H 0.7385 0.5520 0.7465 0.0384 1.0000 Uiso R . . . . . H202 H 0.7723 0.6476 0.6977 0.0371 1.0000 Uiso R . . . . . H211 H 0.8176 0.6617 0.8299 0.0458 1.0000 Uiso R . . . . . H212 H 0.7712 0.7649 0.7917 0.0447 1.0000 Uiso R . . . . . H231 H 0.6911 0.7047 0.4512 0.0307 1.0000 Uiso R . . . . . H232 H 0.6582 0.6033 0.4967 0.0292 1.0000 Uiso R . . . . . H241 H 0.6077 0.6245 0.3508 0.0315 1.0000 Uiso R . . . . . H242 H 0.7131 0.5514 0.3841 0.0329 1.0000 Uiso R . . . . . H261 H 0.6050 0.4221 0.4794 0.0323 1.0000 Uiso R . . . . . H271 H 0.4593 0.2836 0.4840 0.0395 1.0000 Uiso R . . . . . H291 H 0.2905 0.3943 0.3096 0.0401 1.0000 Uiso R . . . . . H301 H 0.4367 0.5350 0.3079 0.0349 1.0000 Uiso R . . . . . H311 H 0.1855 0.2602 0.3855 0.0653 1.0000 Uiso R . . . . . H312 H 0.2671 0.2079 0.4445 0.0649 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 Cl1 0.0902(3) 0.02995(17) 0.0854(3) -0.01110(19) -0.0511(3) 0.00351(19) O1 0.0416(5) 0.0423(5) 0.0255(4) 0.0067(4) 0.0030(4) -0.0094(4) O2 0.0541(6) 0.0320(5) 0.0211(4) 0.0032(4) 0.0085(4) -0.0019(4) O3 0.1151(11) 0.0465(6) 0.0238(5) -0.0031(5) 0.0088(6) -0.0185(7) C1 0.0310(6) 0.0251(5) 0.0236(5) 0.0001(4) -0.0007(5) -0.0073(4) C2 0.0364(6) 0.0257(6) 0.0280(6) 0.0035(5) 0.0011(5) -0.0063(5) C3 0.0245(5) 0.0326(6) 0.0250(6) 0.0061(5) -0.0016(4) -0.0008(5) C4 0.0282(5) 0.0298(6) 0.0218(5) -0.0013(4) -0.0022(4) -0.0012(5) C5 0.0198(5) 0.0234(5) 0.0235(5) 0.0006(4) -0.0034(4) 0.0014(4) C6 0.0220(5) 0.0276(6) 0.0232(5) -0.0011(4) -0.0035(4) -0.0027(4) C7 0.0191(5) 0.0217(5) 0.0228(5) -0.0022(4) -0.0002(4) -0.0037(4) C8 0.0177(5) 0.0209(5) 0.0209(5) -0.0011(4) 0.0003(4) -0.0010(4) C9 0.0193(5) 0.0189(5) 0.0210(5) -0.0007(4) -0.0010(4) -0.0001(4) C10 0.0212(5) 0.0213(5) 0.0215(5) 0.0005(4) 0.0007(4) -0.0005(4) C11 0.0348(6) 0.0199(5) 0.0218(5) -0.0013(4) -0.0027(4) -0.0010(5) C12 0.0301(6) 0.0218(5) 0.0208(5) -0.0023(4) -0.0020(4) -0.0004(4) C13 0.0244(5) 0.0215(5) 0.0208(5) -0.0008(4) 0.0027(4) 0.0014(4) C14 0.0214(5) 0.0198(5) 0.0203(5) -0.0010(4) 0.0013(4) -0.0011(4) C15 0.0362(6) 0.0234(6) 0.0260(6) -0.0009(5) 0.0021(5) -0.0058(5) C16 0.0419(7) 0.0232(6) 0.0297(6) 0.0026(5) -0.0001(5) -0.0052(5) C17 0.0352(6) 0.0233(5) 0.0196(5) 0.0012(4) 0.0038(4) 0.0009(5) C18 0.0284(6) 0.0348(6) 0.0291(6) -0.0023(5) 0.0085(5) 0.0047(5) C19 0.0279(6) 0.0299(6) 0.0302(6) 0.0033(5) 0.0022(5) 0.0071(5) C20 0.0391(7) 0.0264(6) 0.0282(6) 0.0003(5) -0.0071(5) 0.0069(5) C21 0.0556(8) 0.0305(7) 0.0296(7) 0.0022(5) -0.0166(6) 0.0018(6) C22 0.0762(10) 0.0240(6) 0.0222(6) 0.0042(5) -0.0019(6) -0.0039(6) C23 0.0214(5) 0.0262(6) 0.0248(5) -0.0043(4) 0.0002(4) -0.0010(4) C24 0.0276(5) 0.0296(6) 0.0233(5) -0.0038(5) 0.0031(4) -0.0012(5) C25 0.0275(5) 0.0251(5) 0.0226(5) -0.0067(4) 0.0018(4) 0.0023(5) C26 0.0344(6) 0.0294(6) 0.0238(5) -0.0042(5) -0.0019(5) 0.0027(5) C27 0.0422(7) 0.0259(6) 0.0301(6) -0.0008(5) 0.0033(5) 0.0031(5) C28 0.0352(6) 0.0256(6) 0.0427(7) -0.0083(5) 0.0004(6) 0.0009(5) C29 0.0336(6) 0.0330(6) 0.0364(7) -0.0084(5) -0.0065(5) 0.0027(5) C30 0.0331(6) 0.0281(6) 0.0256(6) -0.0041(5) -0.0037(5) 0.0040(5) C31 0.0490(9) 0.0349(7) 0.0805(12) -0.0036(8) -0.0048(9) -0.0095(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.08(6) 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 Cl1 . C31 . 1.8020(19) yes O1 . C3 . 1.2243(15) yes O2 . C17 . 1.4719(14) yes O2 . C22 . 1.3483(19) yes O3 . C22 . 1.2034(18) yes C1 . C2 . 1.5265(16) yes C1 . C10 . 1.5375(15) yes C1 . H11 . 0.989 no C1 . H12 . 1.004 no C2 . C3 . 1.5029(17) yes C2 . H21 . 0.978 no C2 . H22 . 0.959 no C3 . C4 . 1.4686(17) yes C4 . C5 . 1.3425(16) yes C4 . H41 . 0.923 no C5 . C6 . 1.5062(15) yes C5 . C10 . 1.5214(15) yes C6 . C7 . 1.5304(16) yes C6 . H61 . 0.984 no C6 . H62 . 0.983 no C7 . C8 . 1.5432(15) yes C7 . C23 . 1.5333(15) yes C7 . H71 . 0.979 no C8 . C9 . 1.5480(14) yes C8 . C14 . 1.5304(15) yes C8 . H81 . 0.996 no C9 . C10 . 1.5630(15) yes C9 . C11 . 1.5408(15) yes C9 . H91 . 0.981 no C10 . C19 . 1.5468(15) yes C11 . C12 . 1.5321(16) yes C11 . H111 . 0.965 no C11 . H112 . 0.972 no C12 . C13 . 1.5285(16) yes C12 . H121 . 0.985 no C12 . H122 . 0.971 no C13 . C14 . 1.5430(15) yes C13 . C17 . 1.5542(16) yes C13 . C18 . 1.5407(16) yes C14 . C15 . 1.5339(15) yes C14 . H141 . 0.970 no C15 . C16 . 1.5509(17) yes C15 . H151 . 0.958 no C15 . H152 . 1.002 no C16 . C17 . 1.5417(17) yes C16 . H161 . 0.950 no C16 . H162 . 0.974 no C17 . C20 . 1.5363(18) yes C18 . H181 . 0.971 no C18 . H182 . 1.007 no C18 . H183 . 0.978 no C19 . H191 . 0.979 no C19 . H192 . 0.993 no C19 . H193 . 0.971 no C20 . C21 . 1.5240(18) yes C20 . H201 . 0.975 no C20 . H202 . 0.967 no C21 . C22 . 1.500(2) yes C21 . H211 . 0.957 no C21 . H212 . 0.985 no C23 . C24 . 1.5371(15) yes C23 . H231 . 0.949 no C23 . H232 . 1.001 no C24 . C25 . 1.5104(16) yes C24 . H241 . 0.971 no C24 . H242 . 0.992 no C25 . C26 . 1.3920(18) yes C25 . C30 . 1.3938(17) yes C26 . C27 . 1.3878(19) yes C26 . H261 . 0.943 no C27 . C28 . 1.393(2) yes C27 . H271 . 0.964 no C28 . C29 . 1.387(2) yes C28 . C31 . 1.497(2) yes C29 . C30 . 1.3836(19) yes C29 . H291 . 0.971 no C30 . H301 . 0.948 no C31 . H311 . 0.955 no C31 . H312 . 0.965 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 C17 . O2 . C22 . 111.15(11) yes C2 . C1 . C10 . 113.56(10) yes C2 . C1 . H11 . 108.2 no C10 . C1 . H11 . 107.9 no C2 . C1 . H12 . 109.9 no C10 . C1 . H12 . 108.1 no H11 . C1 . H12 . 109.0 no C1 . C2 . C3 . 111.46(10) yes C1 . C2 . H21 . 111.7 no C3 . C2 . H21 . 105.0 no C1 . C2 . H22 . 110.9 no C3 . C2 . H22 . 108.7 no H21 . C2 . H22 . 108.9 no C2 . C3 . O1 . 122.10(11) yes C2 . C3 . C4 . 116.66(10) yes O1 . C3 . C4 . 121.20(12) yes C3 . C4 . C5 . 123.52(11) yes C3 . C4 . H41 . 115.8 no C5 . C4 . H41 . 120.5 no C4 . C5 . C6 . 120.86(10) yes C4 . C5 . C10 . 122.73(10) yes C6 . C5 . C10 . 116.35(9) yes C5 . C6 . C7 . 112.50(9) yes C5 . C6 . H61 . 108.5 no C7 . C6 . H61 . 111.2 no C5 . C6 . H62 . 108.7 no C7 . C6 . H62 . 108.3 no H61 . C6 . H62 . 107.5 no C6 . C7 . C8 . 108.34(9) yes C6 . C7 . C23 . 111.55(9) yes C8 . C7 . C23 . 113.57(9) yes C6 . C7 . H71 . 108.7 no C8 . C7 . H71 . 108.1 no C23 . C7 . H71 . 106.4 no C7 . C8 . C9 . 112.34(9) yes C7 . C8 . C14 . 113.52(9) yes C9 . C8 . C14 . 108.69(8) yes C7 . C8 . H81 . 106.8 no C9 . C8 . H81 . 107.7 no C14 . C8 . H81 . 107.5 no C8 . C9 . C10 . 114.23(9) yes C8 . C9 . C11 . 111.18(9) yes C10 . C9 . C11 . 111.72(9) yes C8 . C9 . H91 . 106.7 no C10 . C9 . H91 . 104.9 no C11 . C9 . H91 . 107.6 no C1 . C10 . C5 . 110.26(9) yes C1 . C10 . C9 . 108.36(9) yes C5 . C10 . C9 . 109.99(9) yes C1 . C10 . C19 . 109.60(9) yes C5 . C10 . C19 . 107.20(9) yes C9 . C10 . C19 . 111.43(9) yes C9 . C11 . C12 . 112.90(9) yes C9 . C11 . H111 . 108.6 no C12 . C11 . H111 . 108.2 no C9 . C11 . H112 . 110.4 no C12 . C11 . H112 . 107.7 no H111 . C11 . H112 . 109.0 no C11 . C12 . C13 . 110.75(9) yes C11 . C12 . H121 . 109.1 no C13 . C12 . H121 . 109.7 no C11 . C12 . H122 . 108.7 no C13 . C12 . H122 . 110.4 no H121 . C12 . H122 . 108.1 no C12 . C13 . C14 . 108.41(9) yes C12 . C13 . C17 . 117.57(10) yes C14 . C13 . C17 . 99.89(9) yes C12 . C13 . C18 . 110.09(9) yes C14 . C13 . C18 . 112.38(10) yes C17 . C13 . C18 . 108.20(10) yes C13 . C14 . C8 . 113.29(9) yes C13 . C14 . C15 . 103.63(9) yes C8 . C14 . C15 . 118.59(9) yes C13 . C14 . H141 . 106.4 no C8 . C14 . H141 . 105.6 no C15 . C14 . H141 . 108.8 no C14 . C15 . C16 . 103.95(9) yes C14 . C15 . H151 . 109.8 no C16 . C15 . H151 . 111.3 no C14 . C15 . H152 . 109.0 no C16 . C15 . H152 . 112.4 no H151 . C15 . H152 . 110.2 no C15 . C16 . C17 . 106.59(10) yes C15 . C16 . H161 . 110.7 no C17 . C16 . H161 . 110.3 no C15 . C16 . H162 . 111.1 no C17 . C16 . H162 . 111.3 no H161 . C16 . H162 . 106.9 no C16 . C17 . C13 . 103.94(9) yes C16 . C17 . O2 . 109.21(10) yes C13 . C17 . O2 . 110.41(9) yes C16 . C17 . C20 . 114.97(11) yes C13 . C17 . C20 . 115.99(10) yes O2 . C17 . C20 . 102.32(10) yes C13 . C18 . H181 . 111.9 no C13 . C18 . H182 . 113.0 no H181 . C18 . H182 . 107.8 no C13 . C18 . H183 . 109.5 no H181 . C18 . H183 . 105.8 no H182 . C18 . H183 . 108.5 no C10 . C19 . H191 . 112.1 no C10 . C19 . H192 . 109.4 no H191 . C19 . H192 . 107.6 no C10 . C19 . H193 . 110.4 no H191 . C19 . H193 . 106.9 no H192 . C19 . H193 . 110.5 no C17 . C20 . C21 . 103.89(11) yes C17 . C20 . H201 . 108.0 no C21 . C20 . H201 . 110.4 no C17 . C20 . H202 . 112.6 no C21 . C20 . H202 . 112.8 no H201 . C20 . H202 . 109.0 no C20 . C21 . C22 . 102.70(12) yes C20 . C21 . H211 . 113.1 no C22 . C21 . H211 . 111.0 no C20 . C21 . H212 . 113.4 no C22 . C21 . H212 . 106.7 no H211 . C21 . H212 . 109.6 no C21 . C22 . O2 . 110.54(11) yes C21 . C22 . O3 . 128.79(16) yes O2 . C22 . O3 . 120.66(16) yes C7 . C23 . C24 . 114.69(9) yes C7 . C23 . H231 . 108.0 no C24 . C23 . H231 . 108.3 no C7 . C23 . H232 . 107.7 no C24 . C23 . H232 . 107.6 no H231 . C23 . H232 . 110.5 no C23 . C24 . C25 . 113.97(10) yes C23 . C24 . H241 . 111.9 no C25 . C24 . H241 . 107.0 no C23 . C24 . H242 . 108.9 no C25 . C24 . H242 . 106.8 no H241 . C24 . H242 . 107.9 no C24 . C25 . C26 . 121.16(11) yes C24 . C25 . C30 . 120.62(11) yes C26 . C25 . C30 . 118.21(11) yes C25 . C26 . C27 . 121.13(12) yes C25 . C26 . H261 . 119.2 no C27 . C26 . H261 . 119.6 no C26 . C27 . C28 . 120.00(12) yes C26 . C27 . H271 . 120.4 no C28 . C27 . H271 . 119.6 no C27 . C28 . C29 . 119.23(13) yes C27 . C28 . C31 . 120.44(14) yes C29 . C28 . C31 . 120.33(14) yes C28 . C29 . C30 . 120.47(12) yes C28 . C29 . H291 . 118.4 no C30 . C29 . H291 . 121.1 no C25 . C30 . C29 . 120.95(12) yes C25 . C30 . H301 . 118.5 no C29 . C30 . H301 . 120.5 no C28 . C31 . Cl1 . 111.12(13) yes C28 . C31 . H311 . 111.8 no Cl1 . C31 . H311 . 108.4 no C28 . C31 . H312 . 109.3 no Cl1 . C31 . H312 . 105.6 no H311 . C31 . H312 . 110.3 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 C19 . H193 . O3 4_656 150.85(4) 0.971 2.533 3.4142(18) yes C21 . H212 . O1 2_675 163.33(4) 0.985 2.525 3.4797(18) yes C27 . H271 . O3 4_646 151.37(4) 0.964 2.524 3.4017(18) yes C30 . H301 . O1 4_645 128.90(4) 0.948 2.565 3.2456(18) yes _iucr_refine_instructions_details_constraints ; # # Punched on 26/09/12 at 14:06:20 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 1,X'S) H ( 11,X'S) H ( 12,X'S) RIDE C ( 2,X'S) H ( 21,X'S) H ( 22,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) H ( 112,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) H ( 183,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) RIDE C ( 23,X'S) H ( 231,X'S) H ( 232,X'S) RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) H ( 312,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 26/09/12 at 14:06:20 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;