# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 loop_ _publ_author_name _publ_author_address L.R.Nassimbeni ; Department of Chemistry University of CApe Town Cape Town Rondebosch 7701 South Africa ; 'Hong Su' ; Department of Chemistry University of CApe Town Cape Town Rondebosch 7701 South Africa ; 'Tanith-Lee Curtin' ; Department of Chemistry University of CApe Town Cape Town Rondebosch 7701 South Africa ; #TrackingRef '- 1.cif' _publ_contact_author 'Luigi R. Nassimbeni' _publ_contact_author_email Luigi.Nassimbeni@uct.ac.za _publ_contact_author_name 'Luigi R. Nassimbeni' data_1 _database_code_depnum_ccdc_archive 'CCDC 885453' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R,R)-(-)-1,6-Bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyn-1,6-diol 3-methylcyclohexanone clathrate ; _chemical_name_common ; (R,R)-(-)-1,6-Bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyn- 1,6-diol 3-methylcyclohexanone clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H44 Cl2 O4' _chemical_formula_weight 707.69 _chemical_absolute_configuration rmad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.4671(12) _cell_length_b 8.9149(13) _cell_length_c 13.1177(19) _cell_angle_alpha 91.426(3) _cell_angle_beta 100.286(2) _cell_angle_gamma 102.834(2) _cell_volume 947.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12536 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9330 _exptl_absorpt_correction_T_max 0.9408 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12536 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.41 _reflns_number_total 9069 _reflns_number_gt 7674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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. C2A1 and C3A1, C2A2 and C3A2, C7B1 and C7B2 were refined with common isotropic displacement parameters. C1A, C4A1, C4A2, C5A, C6A, C7A1 and C7A2 were refined isotropically. Distances of O1-H1, O2-H2, H1-O1A and H2-O1B were restrained to 0.975(5), 0.965(5), 1.735(5) and 1.806(5) respectively. For the guest at site b, the site occupancy factors (s.o.f.) of atoms C7B1 and C7B2 were obtained by calculating a difference electron density map and assigning their values in proportion to their peak heights. These s.o.f. were subsequently fixed in the final refinement. For the guest at site a, the s.o.f. were refined freely. ; _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^)+(0.1208P)^2^+0.3092P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_number_reflns 9069 _refine_ls_number_parameters 419 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1980 _refine_ls_wR_factor_gt 0.1857 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Cl1 Cl 0.5338(4) 0.5157(4) 0.7219(3) 0.0540(2) Uani 1 1 d . . . Cl2 Cl 1.1026(4) 1.0053(4) 0.2001(3) 0.0692(3) Uani 1 1 d . . . O1 O 0.6175(4) 0.9989(4) 0.8698(4) 0.0416(5) Uani 1 1 d D . . H1 H 0.547(3) 1.069(3) 0.845(4) 0.062 Uiso 1 1 d D . . O2 O 0.8612(4) 0.7981(4) 0.3245(3) 0.0392(5) Uani 1 1 d D . . H2 H 0.928(5) 0.731(4) 0.356(3) 0.059 Uiso 1 1 d D . . C1 C 0.5675(5) 0.8528(5) 0.8137(4) 0.0323(6) Uani 1 1 d . . . C2 C 0.6324(5) 0.8685(5) 0.7151(4) 0.0335(6) Uani 1 1 d . . . C3 C 0.6924(5) 0.8876(5) 0.6385(4) 0.0320(6) Uani 1 1 d . . . C4 C 0.7628(5) 0.9075(5) 0.5511(4) 0.0312(5) Uani 1 1 d . . . C5 C 0.8268(5) 0.9267(5) 0.4763(4) 0.0308(5) Uani 1 1 d . . . C6 C 0.8978(5) 0.9445(5) 0.3809(4) 0.0328(6) Uani 1 1 d . . . C7 C 0.6468(5) 0.7400(5) 0.8807(4) 0.0346(6) Uani 1 1 d . . . C8 C 0.6302(5) 0.5867(5) 0.8473(4) 0.0395(7) Uani 1 1 d . . . C9 C 0.6937(6) 0.4840(6) 0.9122(4) 0.0499(8) Uani 1 1 d . . . H9 H 0.6811 0.3799 0.8880 0.060 Uiso 1 1 calc R . . C10 C 0.7755(6) 0.5357(6) 1.0126(4) 0.0544(10) Uani 1 1 d . . . H10 H 0.8178 0.4662 1.0576 0.065 Uiso 1 1 calc R . . C11 C 0.7954(6) 0.6851(6) 1.0469(4) 0.0524(9) Uani 1 1 d . . . H11 H 0.8524 0.7196 1.1155 0.063 Uiso 1 1 calc R . . C12 C 0.7320(5) 0.7888(6) 0.9813(4) 0.0441(7) Uani 1 1 d . . . H12 H 0.7475 0.8932 1.0057 0.053 Uiso 1 1 calc R . . C13 C 0.3790(5) 0.7987(5) 0.7947(4) 0.0340(6) Uani 1 1 d . . . C14 C 0.2809(5) 0.7731(5) 0.6970(4) 0.0379(6) Uani 1 1 d . . . H14 H 0.3305 0.7820 0.6373 0.045 Uiso 1 1 calc R . . C15 C 0.1090(5) 0.7341(5) 0.6852(4) 0.0482(8) Uani 1 1 d . . . H15 H 0.0421 0.7152 0.6178 0.058 Uiso 1 1 calc R . . C16 C 0.0374(5) 0.7231(5) 0.7718(5) 0.0511(9) Uani 1 1 d . . . H16 H -0.0794 0.6992 0.7639 0.061 Uiso 1 1 calc R . . C17 C 0.1336(6) 0.7465(6) 0.8700(5) 0.0552(9) Uani 1 1 d . . . H17 H 0.0830 0.7373 0.9293 0.066 Uiso 1 1 calc R . . C18 C 0.3046(5) 0.7837(6) 0.8820(4) 0.0434(7) Uani 1 1 d . . . H18 H 0.3709 0.7988 0.9496 0.052 Uiso 1 1 calc R . . C19 C 1.0872(5) 1.0092(5) 0.4076(4) 0.0341(6) Uani 1 1 d . . . C20 C 1.1851(6) 1.0345(6) 0.3328(4) 0.0440(7) Uani 1 1 d . . . C21 C 1.3570(6) 1.0839(6) 0.3586(4) 0.0515(9) Uani 1 1 d . . . H21 H 1.4210 1.0985 0.3056 0.062 Uiso 1 1 calc R . . C22 C 1.4326(6) 1.1114(6) 0.4615(4) 0.0504(8) Uani 1 1 d . . . H22 H 1.5492 1.1456 0.4797 0.060 Uiso 1 1 calc R . . C23 C 1.3391(5) 1.0893(5) 0.5378(4) 0.0460(8) Uani 1 1 d . . . H23 H 1.3906 1.1093 0.6088 0.055 Uiso 1 1 calc R . . C24 C 1.1686(5) 1.0374(5) 0.5105(4) 0.0392(7) Uani 1 1 d . . . H24 H 1.1057 1.0208 0.5640 0.047 Uiso 1 1 calc R . . C25 C 0.8109(5) 1.0515(5) 0.3131(4) 0.0370(6) Uani 1 1 d . . . C26 C 0.8356(5) 1.2055(5) 0.3475(4) 0.0444(7) Uani 1 1 d . . . H26 H 0.9056 1.2434 0.4122 0.053 Uiso 1 1 calc R . . C27 C 0.7573(6) 1.3046(6) 0.2867(5) 0.0574(10) Uani 1 1 d . . . H27 H 0.7763 1.4101 0.3097 0.069 Uiso 1 1 calc R . . C28 C 0.6526(6) 1.2499(7) 0.1935(5) 0.0603(11) Uani 1 1 d . . . H28 H 0.5989 1.3169 0.1524 0.072 Uiso 1 1 calc R . . C29 C 0.6264(7) 1.0928(7) 0.1602(4) 0.0637(12) Uani 1 1 d . . . H29 H 0.5553 1.0536 0.0961 0.076 Uiso 1 1 calc R . . C30 C 0.7042(6) 0.9964(6) 0.2209(4) 0.0517(9) Uani 1 1 d . . . H30 H 0.6841 0.8905 0.1988 0.062 Uiso 1 1 calc R . . O1B O 1.0520(5) 0.6150(5) 0.4289(4) 0.0594(7) Uani 1 1 d D . . C1B C 1.1494(6) 0.5623(5) 0.3891(4) 0.0506(8) Uani 1 1 d . F . C2B C 1.1540(6) 0.5703(7) 0.2761(5) 0.0633(11) Uani 1 1 d . . . H2B1 H 1.0803 0.6358 0.2449 0.076 Uiso 1 1 calc R A 1 H2B2 H 1.1125 0.4656 0.2412 0.076 Uiso 1 1 calc R A 1 C4B C 1.4487 0.5504 0.3140 0.0807(16) Uani 1 1 d D . . H4B1 H 1.5608 0.5974 0.3021 0.097 Uiso 1 1 calc R B 1 H4B2 H 1.4190 0.4416 0.2859 0.097 Uiso 1 1 calc R B 1 C6B C 1.2729 0.4879 0.4512 0.0702(13) Uani 1 1 d D . . H6B1 H 1.2426 0.3755 0.4331 0.084 Uiso 1 1 calc R C 1 H6B2 H 1.2728 0.5047 0.5261 0.084 Uiso 1 1 calc R C 1 O1A O 0.3936(5) 1.1632(5) 0.7954(4) 0.0747(9) Uani 1 1 d D E . C1A C 0.2929(9) 1.2269(8) 0.8261(6) 0.0847(15) Uiso 1 1 d . . . C5A C 0.1185(9) 1.1861(9) 0.9601(6) 0.0898(16) Uiso 1 1 d . . . H5A1 H 0.1198 1.2105 1.0343 0.108 Uiso 1 1 calc R D 1 H5A2 H 0.0813 1.0729 0.9461 0.108 Uiso 1 1 calc R D 1 C6A C 0.2832(12) 1.2370(12) 0.9389(8) 0.120(3) Uiso 1 1 d . E . H6A1 H 0.3543 1.1738 0.9764 0.144 Uiso 1 1 calc R . . H6A2 H 0.3280 1.3453 0.9667 0.144 Uiso 1 1 calc R . . C2A1 C 0.1686(8) 1.2950(8) 0.7532(5) 0.0536(14) Uiso 0.687(12) 1 d P E 1 H2A1 H 0.1923 1.4082 0.7673 0.064 Uiso 0.687(12) 1 calc PR E 1 H2A2 H 0.1757 1.2730 0.6800 0.064 Uiso 0.687(12) 1 calc PR E 1 C3A1 C -0.0028(8) 1.2211(8) 0.7723(5) 0.0536(14) Uiso 0.687(12) 1 d P E 1 H3A1 H -0.0274 1.1067 0.7586 0.064 Uiso 0.687(12) 1 calc PR E 1 C4A1 C -0.0036(10) 1.2654(9) 0.8919(6) 0.0977(18) Uiso 0.687(12) 1 d P E 1 H4A1 H 0.0308 1.3786 0.9065 0.117 Uiso 0.687(12) 1 calc PR E 1 H4A2 H -0.1159 1.2294 0.9070 0.117 Uiso 0.687(12) 1 calc PR E 1 C7A1 C -0.1271(10) 1.2887(9) 0.7024(7) 0.0962(18) Uiso 0.687(12) 1 d P E 1 H7A1 H -0.2381 1.2424 0.7141 0.144 Uiso 0.687(12) 1 calc PR E 1 H7A2 H -0.1212 1.2673 0.6297 0.144 Uiso 0.687(12) 1 calc PR E 1 H7A3 H -0.1027 1.4005 0.7180 0.144 Uiso 0.687(12) 1 calc PR E 1 C3B1 C 1.3273(7) 0.6359(7) 0.2579(5) 0.0732(13) Uani 0.71 1 d P F 1 H3B1 H 1.3614 0.7453 0.2871 0.088 Uiso 0.71 1 calc PR F 1 C5B1 C 1.4478 0.5565 0.4294 0.094(2) Uani 0.71 1 d P F 1 H5B1 H 1.4854 0.6649 0.4582 0.113 Uiso 0.71 1 calc PR F 1 H5B2 H 1.5259 0.4978 0.4646 0.113 Uiso 0.71 1 calc PR F 1 C2A2 C 0.1393(17) 1.1823(16) 0.7643(11) 0.057(3) Uiso 0.313(12) 1 d P E 2 H2A3 H 0.0726 1.0894 0.7889 0.068 Uiso 0.313(12) 1 calc PR E 2 H2A4 H 0.1471 1.1611 0.6911 0.068 Uiso 0.313(12) 1 calc PR E 2 C3A2 C 0.0691(18) 1.3177(17) 0.7759(11) 0.057(3) Uiso 0.313(12) 1 d P E 2 H3A2 H 0.1442 1.4218 0.7769 0.068 Uiso 0.313(12) 1 calc PR E 2 C4A2 C -0.0036(10) 1.2654(9) 0.8919(6) 0.0977(18) Uiso 0.313(12) 1 d P E 2 H4A3 H -0.0139 1.3585 0.9305 0.117 Uiso 0.313(12) 1 calc PR E 2 H4A4 H -0.1139 1.1942 0.8747 0.117 Uiso 0.313(12) 1 calc PR E 2 C7A2 C -0.1271(10) 1.2887(9) 0.7024(7) 0.0962(18) Uiso 0.313(12) 1 d P E 2 H7A4 H -0.1717 1.3794 0.7124 0.144 Uiso 0.313(12) 1 calc PR E 2 H7A5 H -0.1983 1.1977 0.7243 0.144 Uiso 0.313(12) 1 calc PR E 2 H7A6 H -0.1227 1.2727 0.6289 0.144 Uiso 0.313(12) 1 calc PR E 2 C3B2 C 1.3273(7) 0.6359(7) 0.2579(5) 0.0732(13) Uani 0.29 1 d P F 2 H3B2 H 1.3277 0.6286 0.1825 0.088 Uiso 0.29 1 calc PR F 2 H3B3 H 1.3619 0.7462 0.2825 0.088 Uiso 0.29 1 calc PR F 2 C5B2 C 1.4478 0.5565 0.4294 0.094(2) Uani 0.29 1 d PD F 2 H5B3 H 1.4801 0.6674 0.4557 0.113 Uiso 0.29 1 calc PR F 2 C7B1 C 1.3310(13) 0.6366(11) 0.1446(8) 0.094(2) Uiso 0.71 1 d P F 1 H7B1 H 1.2516 0.6931 0.1104 0.141 Uiso 0.71 1 calc PR F 1 H7B2 H 1.3018 0.5303 0.1141 0.141 Uiso 0.71 1 calc PR F 1 H7B3 H 1.4420 0.6869 0.1347 0.141 Uiso 0.71 1 calc PR F 1 C7B2 C 1.5708(9) 0.4765(12) 0.4875(6) 0.094(2) Uiso 0.29 1 d PD F 2 H7B4 H 1.5669 0.4827 0.5617 0.141 Uiso 0.29 1 calc PR F 2 H7B5 H 1.6817 0.5264 0.4772 0.141 Uiso 0.29 1 calc PR F 2 H7B6 H 1.5441 0.3681 0.4616 0.141 Uiso 0.29 1 calc PR F 2 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 0.0634(5) 0.0472(4) 0.0481(4) 0.0009(3) -0.0075(4) 0.0205(4) Cl2 0.0574(6) 0.1110(9) 0.0380(4) 0.0075(5) 0.0226(4) 0.0058(5) O1 0.0381(12) 0.0429(12) 0.0427(12) -0.0021(9) 0.0081(9) 0.0074(9) O2 0.0398(11) 0.0423(11) 0.0356(11) -0.0003(9) 0.0068(9) 0.0102(9) C1 0.0257(12) 0.0404(14) 0.0322(13) 0.0075(11) 0.0074(10) 0.0083(11) C2 0.0253(12) 0.0442(15) 0.0319(13) 0.0095(11) 0.0050(10) 0.0094(11) C3 0.0262(12) 0.0371(14) 0.0326(13) 0.0082(11) 0.0042(10) 0.0077(10) C4 0.0284(12) 0.0358(13) 0.0296(13) 0.0075(10) 0.0071(10) 0.0060(10) C5 0.0276(12) 0.0337(13) 0.0312(13) 0.0065(10) 0.0065(10) 0.0057(10) C6 0.0321(14) 0.0379(14) 0.0290(13) 0.0058(11) 0.0090(11) 0.0064(11) C7 0.0279(13) 0.0495(16) 0.0296(13) 0.0127(12) 0.0100(11) 0.0110(12) C8 0.0360(15) 0.0482(17) 0.0351(15) 0.0111(13) 0.0048(12) 0.0120(13) C9 0.0437(18) 0.054(2) 0.056(2) 0.0204(16) 0.0079(16) 0.0176(15) C10 0.0429(18) 0.080(3) 0.0470(19) 0.0318(19) 0.0089(15) 0.0240(18) C11 0.0425(18) 0.087(3) 0.0317(16) 0.0165(16) 0.0069(13) 0.0209(18) C12 0.0389(16) 0.066(2) 0.0310(15) 0.0084(14) 0.0081(12) 0.0179(15) C13 0.0307(14) 0.0333(13) 0.0412(15) 0.0110(11) 0.0129(12) 0.0084(11) C14 0.0327(15) 0.0393(15) 0.0422(16) 0.0149(12) 0.0068(12) 0.0086(12) C15 0.0291(15) 0.0496(19) 0.063(2) 0.0169(16) 0.0010(14) 0.0084(14) C16 0.0318(16) 0.0475(18) 0.077(3) 0.0202(17) 0.0149(16) 0.0098(13) C17 0.0430(19) 0.064(2) 0.070(2) 0.0236(19) 0.0319(18) 0.0164(16) C18 0.0347(15) 0.0577(19) 0.0421(17) 0.0120(14) 0.0159(13) 0.0117(13) C19 0.0317(14) 0.0371(14) 0.0364(14) 0.0099(11) 0.0107(11) 0.0103(11) C20 0.0378(16) 0.0530(19) 0.0432(17) 0.0102(14) 0.0149(13) 0.0083(14) C21 0.0421(18) 0.054(2) 0.066(2) 0.0144(17) 0.0288(17) 0.0119(15) C22 0.0333(15) 0.0495(19) 0.069(2) 0.0177(17) 0.0099(15) 0.0090(14) C23 0.0359(16) 0.0533(19) 0.0473(18) 0.0145(15) 0.0037(13) 0.0095(14) C24 0.0325(14) 0.0457(16) 0.0407(16) 0.0136(13) 0.0091(12) 0.0086(12) C25 0.0356(15) 0.0493(16) 0.0303(13) 0.0131(12) 0.0118(11) 0.0134(12) C26 0.0347(15) 0.0442(17) 0.0533(19) 0.0151(14) 0.0061(14) 0.0073(13) C27 0.046(2) 0.052(2) 0.079(3) 0.0302(19) 0.0151(19) 0.0161(16) C28 0.0423(19) 0.085(3) 0.064(2) 0.046(2) 0.0169(17) 0.0260(19) C29 0.061(2) 0.105(4) 0.0347(17) 0.0188(19) 0.0051(16) 0.040(2) C30 0.052(2) 0.074(2) 0.0330(16) 0.0054(15) 0.0038(14) 0.0257(18) O1B 0.0654(18) 0.0588(16) 0.0581(16) 0.0045(12) 0.0059(14) 0.0277(14) C1B 0.0421(18) 0.0433(18) 0.061(2) 0.0021(15) -0.0040(16) 0.0092(14) C2B 0.046(2) 0.088(3) 0.057(2) 0.008(2) 0.0043(17) 0.022(2) C4B 0.038(2) 0.063(3) 0.142(5) 0.012(3) 0.015(3) 0.0138(18) C6B 0.073(3) 0.058(2) 0.076(3) 0.006(2) -0.013(2) 0.030(2) O1A 0.066(2) 0.067(2) 0.099(3) 0.0137(18) 0.0178(18) 0.0300(16) C3B1 0.061(3) 0.073(3) 0.088(3) 0.012(3) 0.022(3) 0.013(2) C5B1 0.056(3) 0.084(4) 0.127(5) -0.017(3) -0.033(3) 0.026(3) C3B2 0.061(3) 0.073(3) 0.088(3) 0.012(3) 0.022(3) 0.013(2) C5B2 0.056(3) 0.084(4) 0.127(5) -0.017(3) -0.033(3) 0.026(3) _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 Cl1 C8 1.735(3) . ? Cl2 C20 1.746(4) . ? O1 C1 1.419(4) . ? O1 H1 0.978(5) . ? O2 C6 1.428(4) . ? O2 H2 0.961(4) . ? C1 C2 1.490(4) . ? C1 C13 1.534(4) . ? C1 C7 1.539(4) . ? C2 C3 1.204(4) . ? C3 C4 1.381(4) . ? C4 C5 1.201(4) . ? C5 C6 1.479(4) . ? C6 C25 1.537(4) . ? C6 C19 1.552(4) . ? C7 C8 1.393(5) . ? C7 C12 1.394(4) . ? C8 C9 1.395(4) . ? C9 C10 1.389(6) . ? C9 H9 0.9500 . ? C10 C11 1.359(7) . ? C10 H10 0.9500 . ? C11 C12 1.407(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.380(4) . ? C13 C18 1.399(4) . ? C14 C15 1.398(5) . ? C14 H14 0.9500 . ? C15 C16 1.375(6) . ? C15 H15 0.9500 . ? C16 C17 1.379(6) . ? C16 H16 0.9500 . ? C17 C18 1.391(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.386(4) . ? C19 C24 1.391(4) . ? C20 C21 1.399(5) . ? C21 C22 1.377(6) . ? C21 H21 0.9500 . ? C22 C23 1.376(5) . ? C22 H22 0.9500 . ? C23 C24 1.391(5) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.380(5) . ? C25 C26 1.393(5) . ? C26 C27 1.402(5) . ? C26 H26 0.9500 . ? C27 C28 1.382(7) . ? C27 H27 0.9500 . ? C28 C29 1.414(7) . ? C28 H28 0.9500 . ? C29 C30 1.380(5) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? O1B C1B 1.219(5) . ? C1B C6B 1.493(4) . ? C1B C2B 1.494(6) . ? C2B C3B1 1.518(7) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C4B C3B1 1.511(6) . ? C4B C5B1 1.5156(2) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C6B C5B1 1.5514(2) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? O1A C1A 1.240(7) . ? C1A C2A2 1.373(15) . ? C1A C6A 1.497(11) . ? C1A C2A1 1.531(9) . ? C5A C6A 1.447(12) . ? C5A C4A1 1.547(10) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C2A1 C3A1 1.522(9) . ? C2A1 H2A1 0.9900 . ? C2A1 H2A2 0.9900 . ? C3A1 C7A1 1.508(9) . ? C3A1 C4A1 1.611(9) . ? C3A1 H3A1 1.0000 . ? C4A1 H4A1 0.9900 . ? C4A1 H4A2 0.9900 . ? C7A1 H7A1 0.9800 . ? C7A1 H7A2 0.9800 . ? C7A1 H7A3 0.9800 . ? C3B1 C7B1 1.493(11) . ? C3B1 H3B1 1.0000 . ? C5B1 H5B1 0.9900 . ? C5B1 H5B2 0.9900 . ? C2A2 C3A2 1.48(2) . ? C2A2 H2A3 0.9900 . ? C2A2 H2A4 0.9900 . ? C3A2 H3A2 1.0000 . ? C7B1 H7B1 0.9800 . ? C7B1 H7B2 0.9800 . ? C7B1 H7B3 0.9800 . ? C7B2 H7B4 0.9800 . ? C7B2 H7B5 0.9800 . ? C7B2 H7B6 0.9800 . ? 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 C1 O1 H1 113(2) . . ? C6 O2 H2 112(3) . . ? O1 C1 C2 107.7(2) . . ? O1 C1 C13 109.7(2) . . ? C2 C1 C13 112.4(2) . . ? O1 C1 C7 107.1(2) . . ? C2 C1 C7 109.7(2) . . ? C13 C1 C7 109.9(2) . . ? C3 C2 C1 176.2(3) . . ? C2 C3 C4 179.0(3) . . ? C5 C4 C3 178.7(3) . . ? C4 C5 C6 176.9(3) . . ? O2 C6 C5 109.1(2) . . ? O2 C6 C25 107.6(2) . . ? C5 C6 C25 107.5(2) . . ? O2 C6 C19 109.8(2) . . ? C5 C6 C19 111.0(2) . . ? C25 C6 C19 111.7(2) . . ? C8 C7 C12 117.6(3) . . ? C8 C7 C1 122.8(3) . . ? C12 C7 C1 119.5(3) . . ? C7 C8 C9 121.7(3) . . ? C7 C8 Cl1 121.5(2) . . ? C9 C8 Cl1 116.8(3) . . ? C10 C9 C8 119.2(4) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 120.7(4) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C18 119.2(3) . . ? C14 C13 C1 123.4(3) . . ? C18 C13 C1 117.2(3) . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.0(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.0(3) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C20 C19 C24 116.5(3) . . ? C20 C19 C6 123.0(3) . . ? C24 C19 C6 120.5(3) . . ? C19 C20 C21 122.2(3) . . ? C19 C20 Cl2 122.3(3) . . ? C21 C20 Cl2 115.5(3) . . ? C22 C21 C20 119.5(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C19 C24 C23 122.3(3) . . ? C19 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? C30 C25 C26 119.5(3) . . ? C30 C25 C6 121.2(3) . . ? C26 C25 C6 119.2(3) . . ? C25 C26 C27 120.0(4) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C28 C27 C26 120.4(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 119.1(3) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? C30 C29 C28 119.9(4) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C25 121.1(4) . . ? C29 C30 H30 119.5 . . ? C25 C30 H30 119.5 . . ? O1B C1B C6B 121.8(4) . . ? O1B C1B C2B 122.1(3) . . ? C6B C1B C2B 116.1(3) . . ? C1B C2B C3B1 111.6(4) . . ? C1B C2B H2B1 109.3 . . ? C3B1 C2B H2B1 109.3 . . ? C1B C2B H2B2 109.3 . . ? C3B1 C2B H2B2 109.3 . . ? H2B1 C2B H2B2 108.0 . . ? C3B1 C4B C5B1 110.5(3) . . ? C3B1 C4B H4B1 109.5 . . ? C5B1 C4B H4B1 109.5 . . ? C3B1 C4B H4B2 109.5 . . ? C5B1 C4B H4B2 109.5 . . ? H4B1 C4B H4B2 108.1 . . ? C1B C6B C5B1 110.4(2) . . ? C1B C6B H6B1 109.6 . . ? C5B1 C6B H6B1 109.6 . . ? C1B C6B H6B2 109.6 . . ? C5B1 C6B H6B2 109.6 . . ? H6B1 C6B H6B2 108.1 . . ? O1A C1A C2A2 111.7(8) . . ? O1A C1A C6A 120.8(6) . . ? C2A2 C1A C6A 111.8(9) . . ? O1A C1A C2A1 123.3(6) . . ? C2A2 C1A C2A1 39.9(6) . . ? C6A C1A C2A1 115.8(6) . . ? C6A C5A C4A1 111.0(7) . . ? C6A C5A H5A1 109.4 . . ? C4A1 C5A H5A1 109.4 . . ? C6A C5A H5A2 109.4 . . ? C4A1 C5A H5A2 109.4 . . ? H5A1 C5A H5A2 108.0 . . ? C5A C6A C1A 114.3(7) . . ? C5A C6A H6A1 108.7 . . ? C1A C6A H6A1 108.7 . . ? C5A C6A H6A2 108.7 . . ? C1A C6A H6A2 108.7 . . ? H6A1 C6A H6A2 107.6 . . ? C3A1 C2A1 C1A 107.7(5) . . ? C3A1 C2A1 H2A1 110.2 . . ? C1A C2A1 H2A1 110.2 . . ? C3A1 C2A1 H2A2 110.2 . . ? C1A C2A1 H2A2 110.2 . . ? H2A1 C2A1 H2A2 108.5 . . ? C7A1 C3A1 C2A1 108.6(5) . . ? C7A1 C3A1 C4A1 109.7(5) . . ? C2A1 C3A1 C4A1 106.6(5) . . ? C7A1 C3A1 H3A1 110.6 . . ? C2A1 C3A1 H3A1 110.6 . . ? C4A1 C3A1 H3A1 110.6 . . ? C5A C4A1 C3A1 107.6(5) . . ? C5A C4A1 H4A1 110.2 . . ? C3A1 C4A1 H4A1 110.2 . . ? C5A C4A1 H4A2 110.2 . . ? C3A1 C4A1 H4A2 110.2 . . ? H4A1 C4A1 H4A2 108.5 . . ? C3A1 C7A1 H7A1 109.5 . . ? C3A1 C7A1 H7A2 109.5 . . ? H7A1 C7A1 H7A2 109.5 . . ? C3A1 C7A1 H7A3 109.5 . . ? H7A1 C7A1 H7A3 109.5 . . ? H7A2 C7A1 H7A3 109.5 . . ? C7B1 C3B1 C4B 111.4(5) . . ? C7B1 C3B1 C2B 111.0(6) . . ? C4B C3B1 C2B 111.4(4) . . ? C7B1 C3B1 H3B1 107.6 . . ? C4B C3B1 H3B1 107.6 . . ? C2B C3B1 H3B1 107.6 . . ? C4B C5B1 C6B 111.213(4) . . ? C4B C5B1 H5B1 109.4 . . ? C6B C5B1 H5B1 109.4 . . ? C4B C5B1 H5B2 109.4 . . ? C6B C5B1 H5B2 109.4 . . ? H5B1 C5B1 H5B2 108.0 . . ? C1A C2A2 C3A2 102.5(11) . . ? C1A C2A2 H2A3 111.3 . . ? C3A2 C2A2 H2A3 111.3 . . ? C1A C2A2 H2A4 111.3 . . ? C3A2 C2A2 H2A4 111.3 . . ? H2A3 C2A2 H2A4 109.2 . . ? C2A2 C3A2 H3A2 117.4 . . ? C3B1 C7B1 H7B1 109.5 . . ? C3B1 C7B1 H7B2 109.5 . . ? H7B1 C7B1 H7B2 109.5 . . ? C3B1 C7B1 H7B3 109.5 . . ? H7B1 C7B1 H7B3 109.5 . . ? H7B2 C7B1 H7B3 109.5 . . ? H7B4 C7B2 H7B5 109.5 . . ? H7B4 C7B2 H7B6 109.5 . . ? H7B5 C7B2 H7B6 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 31(5) . . . . ? C13 C1 C2 C3 152(5) . . . . ? C7 C1 C2 C3 -85(5) . . . . ? C1 C2 C3 C4 88(20) . . . . ? C2 C3 C4 C5 -80(25) . . . . ? C3 C4 C5 C6 177(100) . . . . ? C4 C5 C6 O2 -39(6) . . . . ? C4 C5 C6 C25 77(6) . . . . ? C4 C5 C6 C19 -160(6) . . . . ? O1 C1 C7 C8 -176.9(3) . . . . ? C2 C1 C7 C8 -60.2(4) . . . . ? C13 C1 C7 C8 63.9(4) . . . . ? O1 C1 C7 C12 6.5(4) . . . . ? C2 C1 C7 C12 123.2(3) . . . . ? C13 C1 C7 C12 -112.7(3) . . . . ? C12 C7 C8 C9 1.1(5) . . . . ? C1 C7 C8 C9 -175.6(3) . . . . ? C12 C7 C8 Cl1 -177.3(2) . . . . ? C1 C7 C8 Cl1 6.0(4) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? Cl1 C8 C9 C10 178.5(3) . . . . ? C8 C9 C10 C11 -0.8(6) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C8 C7 C12 C11 -1.4(5) . . . . ? C1 C7 C12 C11 175.4(3) . . . . ? C10 C11 C12 C7 0.6(5) . . . . ? O1 C1 C13 C14 117.7(3) . . . . ? C2 C1 C13 C14 -2.2(4) . . . . ? C7 C1 C13 C14 -124.7(3) . . . . ? O1 C1 C13 C18 -58.6(3) . . . . ? C2 C1 C13 C18 -178.5(3) . . . . ? C7 C1 C13 C18 58.9(4) . . . . ? C18 C13 C14 C15 0.7(5) . . . . ? C1 C13 C14 C15 -175.6(3) . . . . ? C13 C14 C15 C16 0.8(5) . . . . ? C14 C15 C16 C17 -1.6(6) . . . . ? C15 C16 C17 C18 0.9(6) . . . . ? C16 C17 C18 C13 0.6(6) . . . . ? C14 C13 C18 C17 -1.4(5) . . . . ? C1 C13 C18 C17 175.1(3) . . . . ? O2 C6 C19 C20 58.1(4) . . . . ? C5 C6 C19 C20 178.8(3) . . . . ? C25 C6 C19 C20 -61.2(4) . . . . ? O2 C6 C19 C24 -118.5(3) . . . . ? C5 C6 C19 C24 2.2(4) . . . . ? C25 C6 C19 C24 122.2(3) . . . . ? C24 C19 C20 C21 0.7(5) . . . . ? C6 C19 C20 C21 -176.0(3) . . . . ? C24 C19 C20 Cl2 -179.7(3) . . . . ? C6 C19 C20 Cl2 3.5(4) . . . . ? C19 C20 C21 C22 -1.2(6) . . . . ? Cl2 C20 C21 C22 179.3(3) . . . . ? C20 C21 C22 C23 0.4(6) . . . . ? C21 C22 C23 C24 0.7(6) . . . . ? C20 C19 C24 C23 0.4(5) . . . . ? C6 C19 C24 C23 177.3(3) . . . . ? C22 C23 C24 C19 -1.2(5) . . . . ? O2 C6 C25 C30 6.6(4) . . . . ? C5 C6 C25 C30 -110.8(3) . . . . ? C19 C6 C25 C30 127.2(3) . . . . ? O2 C6 C25 C26 -175.8(3) . . . . ? C5 C6 C25 C26 66.8(3) . . . . ? C19 C6 C25 C26 -55.2(4) . . . . ? C30 C25 C26 C27 -2.4(5) . . . . ? C6 C25 C26 C27 -180.0(3) . . . . ? C25 C26 C27 C28 1.3(6) . . . . ? C26 C27 C28 C29 -0.4(6) . . . . ? C27 C28 C29 C30 0.4(6) . . . . ? C28 C29 C30 C25 -1.4(6) . . . . ? C26 C25 C30 C29 2.4(5) . . . . ? C6 C25 C30 C29 180.0(3) . . . . ? O1B C1B C2B C3B1 129.2(5) . . . . ? C6B C1B C2B C3B1 -50.0(5) . . . . ? O1B C1B C6B C5B1 -129.7(3) . . . . ? C2B C1B C6B C5B1 49.4(4) . . . . ? C4A1 C5A C6A C1A -50.8(9) . . . . ? O1A C1A C6A C5A -129.8(8) . . . . ? C2A2 C1A C6A C5A 4.9(11) . . . . ? C2A1 C1A C6A C5A 48.4(10) . . . . ? O1A C1A C2A1 C3A1 124.6(7) . . . . ? C2A2 C1A C2A1 C3A1 40.1(10) . . . . ? C6A C1A C2A1 C3A1 -53.6(8) . . . . ? C1A C2A1 C3A1 C7A1 179.0(5) . . . . ? C1A C2A1 C3A1 C4A1 60.8(6) . . . . ? C6A C5A C4A1 C3A1 59.6(8) . . . . ? C7A1 C3A1 C4A1 C5A 176.9(6) . . . . ? C2A1 C3A1 C4A1 C5A -65.6(7) . . . . ? C5B1 C4B C3B1 C7B1 177.7(5) . . . . ? C5B1 C4B C3B1 C2B -57.8(4) . . . . ? C1B C2B C3B1 C7B1 177.5(5) . . . . ? C1B C2B C3B1 C4B 52.7(6) . . . . ? C3B1 C4B C5B1 C6B 57.6(2) . . . . ? C1B C6B C5B1 C4B -52.5(2) . . . . ? O1A C1A C2A2 C3A2 -151.8(9) . . . . ? C6A C1A C2A2 C3A2 69.3(11) . . . . ? C2A1 C1A C2A2 C3A2 -35.4(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1A 0.978(5) 1.739(5) 2.708(4) 170(3) . O2 H2 O1B 0.961(4) 1.806(4) 2.764(3) 174(4) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.728 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.060 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 885454' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R,R)-(-)-1,6-Bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyn-1,6-diol 3-methylcyclohexanone clathrate ; _chemical_name_common ; (R,R)-(-)-1,6-Bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyn- 1,6-diol 3-methylcyclohexanone clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H44 Cl2 O4' _chemical_formula_weight 707.69 _chemical_absolute_configuration rmad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.5231(8) _cell_length_b 8.7974(9) _cell_length_c 13.1011(13) _cell_angle_alpha 91.629(2) _cell_angle_beta 99.871(2) _cell_angle_gamma 102.048(2) _cell_volume 944.37(16) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12269 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 26.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9505 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12269 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.51 _reflns_number_total 7627 _reflns_number_gt 5808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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. ; _iucr_refine_instructions_details ; Distances of O1-H1, O2-H2, H1-O1A and H2-O1B were restrained to 0.975(5), 0.965(5), 1.751(5) and 1.836(5) respectively. ; _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^)+(0.1673P)^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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(10) _refine_ls_number_reflns 7627 _refine_ls_number_parameters 459 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0791 _refine_ls_wR_factor_ref 0.2326 _refine_ls_wR_factor_gt 0.2132 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 Cl1 Cl 0.3896(2) -0.12743(18) 1.19318(13) 0.0717(4) Uani 1 1 d . . . Cl2 Cl 0.9403(2) 0.3593(2) 0.67130(13) 0.0864(6) Uani 1 1 d . . . O1 O 0.4581(3) 0.3598(3) 1.3476(2) 0.0355(6) Uani 1 1 d D . . H1 H 0.393(3) 0.432(3) 1.318(4) 0.053 Uiso 1 1 d D . . O2 O 0.6984(3) 0.1512(3) 0.7987(2) 0.0338(6) Uani 1 1 d D . . H2 H 0.777(4) 0.1063(17) 0.843(3) 0.051 Uiso 1 1 d D . . C1 C 0.4127(4) 0.2114(4) 1.2908(3) 0.0275(8) Uani 1 1 d . . . C2 C 0.4777(4) 0.2280(4) 1.1926(3) 0.0274(8) Uani 1 1 d . . . C3 C 0.5373(4) 0.2468(5) 1.1157(3) 0.0268(7) Uani 1 1 d . . . C4 C 0.6062(4) 0.2668(4) 1.0281(3) 0.0266(7) Uani 1 1 d . . . C5 C 0.6673(4) 0.2833(4) 0.9519(3) 0.0262(7) Uani 1 1 d . . . C6 C 0.7360(4) 0.2988(4) 0.8546(3) 0.0269(8) Uani 1 1 d . . . C7 C 0.4928(4) 0.0983(5) 1.3576(3) 0.0307(8) Uani 1 1 d . . . C8 C 0.4793(5) -0.0563(5) 1.3220(3) 0.0370(9) Uani 1 1 d . . . C9 C 0.5463(5) -0.1586(6) 1.3860(4) 0.0450(11) Uani 1 1 d . . . H9 H 0.5362 -0.2634 1.3613 0.054 Uiso 1 1 calc R . . C10 C 0.6273(6) -0.1080(6) 1.4852(4) 0.0508(13) Uani 1 1 d . . . H10 H 0.6721 -0.1787 1.5287 0.061 Uiso 1 1 calc R . . C11 C 0.6432(5) 0.0355(7) 1.5204(3) 0.0491(13) Uani 1 1 d . . . H11 H 0.6990 0.0678 1.5892 0.059 Uiso 1 1 calc R . . C12 C 0.5777(5) 0.1452(6) 1.4565(3) 0.0407(10) Uani 1 1 d . . . H12 H 0.5927 0.2502 1.4824 0.049 Uiso 1 1 calc R . . C13 C 0.2262(4) 0.1572(4) 1.2720(3) 0.0278(8) Uani 1 1 d . . . C14 C 0.1310(5) 0.1305(5) 1.1742(3) 0.0330(9) Uani 1 1 d . . . H14 H 0.1804 0.1399 1.1143 0.040 Uiso 1 1 calc R . . C15 C -0.0391(5) 0.0894(5) 1.1639(4) 0.0462(11) Uani 1 1 d . . . H15 H -0.1047 0.0698 1.0966 0.055 Uiso 1 1 calc R . . C16 C -0.1118(5) 0.0771(5) 1.2486(4) 0.0447(11) Uani 1 1 d . . . H16 H -0.2274 0.0522 1.2400 0.054 Uiso 1 1 calc R . . C17 C -0.0182(6) 0.1005(6) 1.3474(4) 0.0504(12) Uani 1 1 d . . . H17 H -0.0691 0.0898 1.4067 0.060 Uiso 1 1 calc R . . C18 C 0.1534(5) 0.1405(5) 1.3592(3) 0.0401(10) Uani 1 1 d . . . H18 H 0.2189 0.1559 1.4266 0.048 Uiso 1 1 calc R . . C19 C 0.9224(4) 0.3621(4) 0.8787(3) 0.0288(8) Uani 1 1 d . . . C20 C 1.0181(6) 0.3860(6) 0.8010(4) 0.0471(11) Uani 1 1 d . . . C21 C 1.1851(7) 0.4327(6) 0.8255(5) 0.0589(15) Uani 1 1 d . . . H21 H 1.2465 0.4464 0.7711 0.071 Uiso 1 1 calc R . . C22 C 1.2636(6) 0.4593(6) 0.9244(5) 0.0582(14) Uani 1 1 d . . . H22 H 1.3790 0.4924 0.9395 0.070 Uiso 1 1 calc R . . C23 C 1.1772(5) 0.4387(6) 1.0033(4) 0.0496(12) Uani 1 1 d . . . H23 H 1.2320 0.4578 1.0735 0.060 Uiso 1 1 calc R . . C24 C 1.0084(5) 0.3895(5) 0.9802(3) 0.0354(9) Uani 1 1 d . . . H24 H 0.9495 0.3741 1.0358 0.042 Uiso 1 1 calc R . . C25 C 0.6500(5) 0.4093(5) 0.7876(3) 0.0316(8) Uani 1 1 d . . . C26 C 0.6740(5) 0.5640(5) 0.8223(4) 0.0416(10) Uani 1 1 d . . . H26 H 0.7424 0.6013 0.8870 0.050 Uiso 1 1 calc R . . C27 C 0.5976(6) 0.6646(6) 0.7621(5) 0.0516(13) Uani 1 1 d . . . H27 H 0.6151 0.7711 0.7854 0.062 Uiso 1 1 calc R . . C28 C 0.4949(6) 0.6089(7) 0.6672(4) 0.0531(14) Uani 1 1 d . . . H28 H 0.4426 0.6775 0.6259 0.064 Uiso 1 1 calc R . . C29 C 0.4697(6) 0.4520(6) 0.6335(4) 0.0496(12) Uani 1 1 d . . . H29 H 0.4002 0.4134 0.5693 0.060 Uiso 1 1 calc R . . C30 C 0.5463(6) 0.3534(6) 0.6941(3) 0.0433(10) Uani 1 1 d . . . H30 H 0.5280 0.2464 0.6718 0.052 Uiso 1 1 calc R . . O1A O 0.2456(5) 0.5303(5) 1.2595(3) 0.0681(11) Uani 1 1 d D . . C1A C 0.1448(7) 0.5941(7) 1.2932(5) 0.0611(14) Uani 1 1 d . . . C2A C 0.1366(9) 0.6032(10) 1.4044(5) 0.083(2) Uani 1 1 d . . . H2A1 H 0.1712 0.7136 1.4313 0.100 Uiso 1 1 calc R . . H2A2 H 0.2146 0.5459 1.4418 0.100 Uiso 1 1 calc R . . C3A C -0.0298(9) 0.5380(9) 1.4274(5) 0.0768(18) Uani 1 1 d . . . H3A1 H -0.0318 0.5625 1.5013 0.092 Uiso 1 1 calc R . . H3A2 H -0.0571 0.4234 1.4141 0.092 Uiso 1 1 calc R . . C4A C -0.1560(7) 0.6107(8) 1.3571(6) 0.0749(18) Uani 1 1 d . . . H4A1 H -0.2668 0.5623 1.3686 0.090 Uiso 1 1 calc R . . H4A2 H -0.1355 0.7234 1.3771 0.090 Uiso 1 1 calc R . . C5A C -0.1490(8) 0.5885(8) 1.2419(6) 0.0708(17) Uani 1 1 d . . . H5A H -0.1678 0.4738 1.2252 0.085 Uiso 1 1 calc R . . C6A C 0.0193(7) 0.6586(7) 1.2231(5) 0.0629(15) Uani 1 1 d . . . H6A1 H 0.0258 0.6353 1.1498 0.075 Uiso 1 1 calc R . . H6A2 H 0.0418 0.7731 1.2361 0.075 Uiso 1 1 calc R . . C7A C -0.2778(9) 0.6441(9) 1.1729(7) 0.094(2) Uani 1 1 d . . . H7A1 H -0.2602 0.7575 1.1837 0.141 Uiso 1 1 calc R . . H7A2 H -0.3846 0.5952 1.1885 0.141 Uiso 1 1 calc R . . H7A3 H -0.2743 0.6165 1.1004 0.141 Uiso 1 1 calc R . . O1B O 0.8896(4) -0.0338(4) 0.9038(3) 0.0503(8) Uani 1 1 d D . . C1B C 0.9893(5) -0.0838(5) 0.8661(4) 0.0418(10) Uani 1 1 d . . . C2B C 0.9941(6) -0.0780(7) 0.7521(4) 0.0522(12) Uani 1 1 d . . . H2B1 H 0.9190 -0.0134 0.7202 0.063 Uiso 1 1 calc R . . H2B2 H 0.9561 -0.1845 0.7183 0.063 Uiso 1 1 calc R . . C3B C 1.1678(7) -0.0094(7) 0.7335(5) 0.0577(13) Uani 1 1 d . . . H3B H 1.1980 0.1026 0.7598 0.069 Uiso 1 1 calc R . . C4B C 1.2890(7) -0.0929(7) 0.7934(6) 0.0670(16) Uani 1 1 d . . . H4B1 H 1.4001 -0.0450 0.7823 0.080 Uiso 1 1 calc R . . H4B2 H 1.2634 -0.2033 0.7667 0.080 Uiso 1 1 calc R . . C5B C 1.2855(7) -0.0851(8) 0.9089(6) 0.0738(18) Uani 1 1 d . . . H5B1 H 1.3185 0.0248 0.9369 0.089 Uiso 1 1 calc R . . H5B2 H 1.3645 -0.1425 0.9452 0.089 Uiso 1 1 calc R . . C6B C 1.1134(7) -0.1563(6) 0.9293(4) 0.0545(13) Uani 1 1 d . . . H6B1 H 1.0872 -0.2700 0.9115 0.065 Uiso 1 1 calc R . . H6B2 H 1.1105 -0.1395 1.0040 0.065 Uiso 1 1 calc R . . C7B C 1.1710(11) -0.0165(12) 0.6191(6) 0.102(3) Uani 1 1 d . . . H7B1 H 1.0915 0.0389 0.5833 0.154 Uiso 1 1 calc R . . H7B2 H 1.1433 -0.1256 0.5919 0.154 Uiso 1 1 calc R . . H7B3 H 1.2804 0.0323 0.6077 0.154 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 Cl1 0.0786(9) 0.0641(8) 0.0699(9) 0.0046(6) -0.0001(7) 0.0207(7) Cl2 0.0777(10) 0.1320(15) 0.0544(8) 0.0155(9) 0.0313(7) 0.0168(10) O1 0.0318(14) 0.0386(16) 0.0365(15) 0.0007(12) 0.0087(11) 0.0065(12) O2 0.0393(15) 0.0340(14) 0.0303(14) 0.0020(11) 0.0079(11) 0.0116(12) C1 0.0258(17) 0.035(2) 0.0239(17) 0.0084(15) 0.0090(14) 0.0066(15) C2 0.0202(16) 0.036(2) 0.0266(18) 0.0101(15) 0.0030(13) 0.0068(15) C3 0.0219(16) 0.034(2) 0.0257(18) 0.0070(15) 0.0076(13) 0.0059(14) C4 0.0241(17) 0.0297(18) 0.0274(18) 0.0074(14) 0.0065(14) 0.0066(14) C5 0.0225(16) 0.0292(18) 0.0297(19) 0.0077(15) 0.0093(14) 0.0076(14) C6 0.0263(18) 0.0308(19) 0.0259(18) 0.0063(15) 0.0097(14) 0.0069(15) C7 0.0264(18) 0.043(2) 0.0290(19) 0.0150(16) 0.0134(15) 0.0123(16) C8 0.033(2) 0.042(2) 0.040(2) 0.0154(19) 0.0123(17) 0.0120(18) C9 0.036(2) 0.048(3) 0.054(3) 0.023(2) 0.009(2) 0.013(2) C10 0.046(2) 0.064(3) 0.056(3) 0.040(3) 0.021(2) 0.029(2) C11 0.041(2) 0.091(4) 0.025(2) 0.023(2) 0.0112(17) 0.029(2) C12 0.041(2) 0.063(3) 0.025(2) 0.0112(19) 0.0107(17) 0.023(2) C13 0.0235(17) 0.0267(18) 0.037(2) 0.0099(15) 0.0140(15) 0.0055(14) C14 0.0285(19) 0.033(2) 0.041(2) 0.0144(17) 0.0092(16) 0.0099(16) C15 0.028(2) 0.046(3) 0.065(3) 0.017(2) 0.0031(19) 0.0101(18) C16 0.025(2) 0.039(2) 0.073(3) 0.020(2) 0.018(2) 0.0044(17) C17 0.039(2) 0.051(3) 0.074(3) 0.021(2) 0.037(2) 0.013(2) C18 0.032(2) 0.049(2) 0.040(2) 0.0091(19) 0.0160(17) 0.0019(17) C19 0.0292(19) 0.034(2) 0.0297(19) 0.0111(15) 0.0160(15) 0.0105(15) C20 0.054(3) 0.052(3) 0.048(3) 0.011(2) 0.035(2) 0.017(2) C21 0.062(3) 0.051(3) 0.083(4) 0.017(3) 0.058(3) 0.017(2) C22 0.030(2) 0.056(3) 0.096(4) 0.030(3) 0.022(2) 0.013(2) C23 0.028(2) 0.053(3) 0.065(3) 0.024(2) 0.002(2) 0.0056(19) C24 0.0280(19) 0.041(2) 0.039(2) 0.0166(18) 0.0100(16) 0.0070(17) C25 0.0330(19) 0.040(2) 0.0280(19) 0.0134(16) 0.0133(15) 0.0129(16) C26 0.032(2) 0.042(2) 0.052(3) 0.012(2) 0.0057(18) 0.0091(18) C27 0.049(3) 0.042(3) 0.073(3) 0.029(2) 0.021(2) 0.019(2) C28 0.041(2) 0.086(4) 0.046(3) 0.042(3) 0.020(2) 0.030(2) C29 0.056(3) 0.072(3) 0.030(2) 0.014(2) 0.0093(19) 0.032(2) C30 0.047(2) 0.063(3) 0.026(2) 0.0041(19) 0.0084(17) 0.024(2) O1A 0.063(2) 0.066(2) 0.079(3) 0.000(2) 0.003(2) 0.032(2) C1A 0.051(3) 0.060(3) 0.070(4) 0.008(3) 0.001(3) 0.014(3) C2A 0.072(4) 0.110(6) 0.069(4) 0.010(4) 0.001(3) 0.034(4) C3A 0.077(4) 0.096(5) 0.066(4) 0.018(3) 0.015(3) 0.035(4) C4A 0.049(3) 0.061(4) 0.117(6) 0.014(3) 0.022(3) 0.009(3) C5A 0.056(3) 0.062(4) 0.089(5) 0.003(3) -0.005(3) 0.015(3) C6A 0.064(3) 0.058(3) 0.069(4) 0.006(3) 0.002(3) 0.025(3) C7A 0.068(4) 0.075(4) 0.127(7) -0.006(4) -0.022(4) 0.025(3) O1B 0.061(2) 0.0465(19) 0.0506(19) 0.0068(14) 0.0123(16) 0.0243(16) C1B 0.042(2) 0.030(2) 0.052(3) 0.0020(19) 0.001(2) 0.0089(18) C2B 0.041(2) 0.071(3) 0.048(3) 0.011(2) 0.007(2) 0.020(2) C3B 0.059(3) 0.052(3) 0.066(3) 0.007(2) 0.024(3) 0.010(2) C4B 0.044(3) 0.059(3) 0.101(5) 0.009(3) 0.021(3) 0.012(2) C5B 0.047(3) 0.068(4) 0.097(5) 0.009(3) -0.015(3) 0.015(3) C6B 0.059(3) 0.053(3) 0.054(3) 0.010(2) -0.001(2) 0.027(2) C7B 0.091(5) 0.140(8) 0.080(5) 0.022(5) 0.027(4) 0.021(5) _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 Cl1 C8 1.767(5) . ? Cl2 C20 1.705(5) . ? O1 C1 1.430(5) . ? O1 H1 0.976(2) . ? O2 C6 1.420(5) . ? O2 H2 0.964(2) . ? C1 C2 1.485(5) . ? C1 C7 1.533(5) . ? C1 C13 1.535(5) . ? C2 C3 1.204(5) . ? C3 C4 1.376(4) . ? C4 C5 1.202(5) . ? C5 C6 1.490(5) . ? C6 C25 1.541(5) . ? C6 C19 1.543(5) . ? C7 C12 1.377(6) . ? C7 C8 1.400(6) . ? C8 C9 1.390(6) . ? C9 C10 1.377(8) . ? C9 H9 0.9500 . ? C10 C11 1.303(8) . ? C10 H10 0.9500 . ? C11 C12 1.433(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.380(6) . ? C13 C18 1.387(5) . ? C14 C15 1.401(6) . ? C14 H14 0.9500 . ? C15 C16 1.356(7) . ? C15 H15 0.9500 . ? C16 C17 1.384(8) . ? C16 H16 0.9500 . ? C17 C18 1.412(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.392(6) . ? C19 C20 1.403(5) . ? C20 C21 1.375(8) . ? C21 C22 1.343(9) . ? C21 H21 0.9500 . ? C22 C23 1.363(8) . ? C22 H22 0.9500 . ? C23 C24 1.391(6) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.384(6) . ? C25 C30 1.392(6) . ? C26 C27 1.390(6) . ? C26 H26 0.9500 . ? C27 C28 1.403(8) . ? C27 H27 0.9500 . ? C28 C29 1.398(8) . ? C28 H28 0.9500 . ? C29 C30 1.381(6) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? O1A C1A 1.252(7) . ? C1A C2A 1.470(10) . ? C1A C6A 1.502(8) . ? C2A C3A 1.499(11) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.547(9) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.530(10) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C7A 1.474(9) . ? C5A C6A 1.503(10) . ? C5A H5A 1.0000 . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? O1B C1B 1.202(6) . ? C1B C6B 1.491(6) . ? C1B C2B 1.503(7) . ? C2B C3B 1.541(7) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C7B 1.503(10) . ? C3B C4B 1.515(8) . ? C3B H3B 1.0000 . ? C4B C5B 1.518(11) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.542(9) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B H7B1 0.9800 . ? C7B H7B2 0.9800 . ? C7B H7B3 0.9800 . ? 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 C1 O1 H1 112(2) . . ? C6 O2 H2 96.7(11) . . ? O1 C1 C2 108.0(3) . . ? O1 C1 C7 107.1(3) . . ? C2 C1 C7 109.8(3) . . ? O1 C1 C13 108.9(3) . . ? C2 C1 C13 112.5(3) . . ? C7 C1 C13 110.3(3) . . ? C3 C2 C1 176.6(4) . . ? C2 C3 C4 179.3(4) . . ? C5 C4 C3 179.4(3) . . ? C4 C5 C6 177.3(4) . . ? O2 C6 C5 109.2(3) . . ? O2 C6 C25 107.9(3) . . ? C5 C6 C25 107.5(3) . . ? O2 C6 C19 110.2(3) . . ? C5 C6 C19 111.0(3) . . ? C25 C6 C19 111.0(3) . . ? C12 C7 C8 117.7(4) . . ? C12 C7 C1 120.6(4) . . ? C8 C7 C1 121.7(3) . . ? C9 C8 C7 120.6(4) . . ? C9 C8 Cl1 116.9(4) . . ? C7 C8 Cl1 122.4(3) . . ? C10 C9 C8 120.0(5) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.9(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.9(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 119.9(5) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C18 119.9(4) . . ? C14 C13 C1 123.1(3) . . ? C18 C13 C1 116.9(3) . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 121.1(4) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 120.3(4) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C18 119.3(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C13 C18 C17 119.8(4) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C24 C19 C20 115.4(4) . . ? C24 C19 C6 121.7(3) . . ? C20 C19 C6 122.8(4) . . ? C21 C20 C19 121.3(5) . . ? C21 C20 Cl2 114.8(4) . . ? C19 C20 Cl2 123.9(4) . . ? C22 C21 C20 121.6(4) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C23 119.9(5) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 119.5(5) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C23 C24 C19 122.4(4) . . ? C23 C24 H24 118.8 . . ? C19 C24 H24 118.8 . . ? C26 C25 C30 120.2(4) . . ? C26 C25 C6 119.5(4) . . ? C30 C25 C6 120.3(4) . . ? C25 C26 C27 119.9(4) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 120.0(5) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C30 C29 C28 119.7(4) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C25 120.6(5) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? O1A C1A C2A 121.7(5) . . ? O1A C1A C6A 122.5(6) . . ? C2A C1A C6A 115.7(6) . . ? C1A C2A C3A 113.8(6) . . ? C1A C2A H2A1 108.8 . . ? C3A C2A H2A1 108.8 . . ? C1A C2A H2A2 108.8 . . ? C3A C2A H2A2 108.8 . . ? H2A1 C2A H2A2 107.7 . . ? C2A C3A C4A 109.0(6) . . ? C2A C3A H3A1 109.9 . . ? C4A C3A H3A1 109.9 . . ? C2A C3A H3A2 109.9 . . ? C4A C3A H3A2 109.9 . . ? H3A1 C3A H3A2 108.3 . . ? C5A C4A C3A 112.4(5) . . ? C5A C4A H4A1 109.1 . . ? C3A C4A H4A1 109.1 . . ? C5A C4A H4A2 109.1 . . ? C3A C4A H4A2 109.1 . . ? H4A1 C4A H4A2 107.9 . . ? C7A C5A C6A 112.9(6) . . ? C7A C5A C4A 113.4(6) . . ? C6A C5A C4A 110.0(5) . . ? C7A C5A H5A 106.7 . . ? C6A C5A H5A 106.7 . . ? C4A C5A H5A 106.7 . . ? C1A C6A C5A 110.5(5) . . ? C1A C6A H6A1 109.6 . . ? C5A C6A H6A1 109.6 . . ? C1A C6A H6A2 109.6 . . ? C5A C6A H6A2 109.6 . . ? H6A1 C6A H6A2 108.1 . . ? C5A C7A H7A1 109.5 . . ? C5A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C5A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? O1B C1B C6B 122.0(4) . . ? O1B C1B C2B 121.6(4) . . ? C6B C1B C2B 116.4(4) . . ? C1B C2B C3B 111.3(4) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C7B C3B C4B 112.0(6) . . ? C7B C3B C2B 110.0(5) . . ? C4B C3B C2B 110.5(4) . . ? C7B C3B H3B 108.1 . . ? C4B C3B H3B 108.1 . . ? C2B C3B H3B 108.1 . . ? C3B C4B C5B 111.8(5) . . ? C3B C4B H4B1 109.3 . . ? C5B C4B H4B1 109.3 . . ? C3B C4B H4B2 109.3 . . ? C5B C4B H4B2 109.3 . . ? H4B1 C4B H4B2 107.9 . . ? C4B C5B C6B 110.8(5) . . ? C4B C5B H5B1 109.5 . . ? C6B C5B H5B1 109.5 . . ? C4B C5B H5B2 109.5 . . ? C6B C5B H5B2 109.5 . . ? H5B1 C5B H5B2 108.1 . . ? C1B C6B C5B 110.6(5) . . ? C1B C6B H6B1 109.5 . . ? C5B C6B H6B1 109.5 . . ? C1B C6B H6B2 109.5 . . ? C5B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 108.1 . . ? C3B C7B H7B1 109.5 . . ? C3B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C3B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 36(7) . . . . ? C7 C1 C2 C3 -81(6) . . . . ? C13 C1 C2 C3 156(6) . . . . ? C1 C2 C3 C4 95(37) . . . . ? C2 C3 C4 C5 -14(58) . . . . ? C3 C4 C5 C6 103(37) . . . . ? C4 C5 C6 O2 -42(8) . . . . ? C4 C5 C6 C25 75(8) . . . . ? C4 C5 C6 C19 -163(8) . . . . ? O1 C1 C7 C12 5.0(4) . . . . ? C2 C1 C7 C12 122.0(4) . . . . ? C13 C1 C7 C12 -113.4(4) . . . . ? O1 C1 C7 C8 -176.7(3) . . . . ? C2 C1 C7 C8 -59.7(4) . . . . ? C13 C1 C7 C8 64.9(4) . . . . ? C12 C7 C8 C9 1.6(6) . . . . ? C1 C7 C8 C9 -176.8(4) . . . . ? C12 C7 C8 Cl1 -174.4(3) . . . . ? C1 C7 C8 Cl1 7.3(5) . . . . ? C7 C8 C9 C10 -0.2(6) . . . . ? Cl1 C8 C9 C10 175.9(4) . . . . ? C8 C9 C10 C11 -0.4(7) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C8 C7 C12 C11 -2.3(6) . . . . ? C1 C7 C12 C11 176.1(4) . . . . ? C10 C11 C12 C7 1.7(6) . . . . ? O1 C1 C13 C14 118.5(4) . . . . ? C2 C1 C13 C14 -1.3(5) . . . . ? C7 C1 C13 C14 -124.3(4) . . . . ? O1 C1 C13 C18 -59.3(4) . . . . ? C2 C1 C13 C18 -179.0(3) . . . . ? C7 C1 C13 C18 58.0(4) . . . . ? C18 C13 C14 C15 1.2(6) . . . . ? C1 C13 C14 C15 -176.5(4) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C14 C15 C16 C17 -2.0(7) . . . . ? C15 C16 C17 C18 1.3(7) . . . . ? C14 C13 C18 C17 -1.8(6) . . . . ? C1 C13 C18 C17 176.0(4) . . . . ? C16 C17 C18 C13 0.6(7) . . . . ? O2 C6 C19 C24 -117.5(4) . . . . ? C5 C6 C19 C24 3.5(5) . . . . ? C25 C6 C19 C24 123.1(4) . . . . ? O2 C6 C19 C20 58.1(5) . . . . ? C5 C6 C19 C20 179.2(4) . . . . ? C25 C6 C19 C20 -61.3(5) . . . . ? C24 C19 C20 C21 0.3(6) . . . . ? C6 C19 C20 C21 -175.6(4) . . . . ? C24 C19 C20 Cl2 179.8(4) . . . . ? C6 C19 C20 Cl2 3.9(6) . . . . ? C19 C20 C21 C22 -0.9(8) . . . . ? Cl2 C20 C21 C22 179.6(4) . . . . ? C20 C21 C22 C23 0.6(8) . . . . ? C21 C22 C23 C24 0.3(8) . . . . ? C22 C23 C24 C19 -0.9(7) . . . . ? C20 C19 C24 C23 0.6(6) . . . . ? C6 C19 C24 C23 176.6(4) . . . . ? O2 C6 C25 C26 -176.7(3) . . . . ? C5 C6 C25 C26 65.7(4) . . . . ? C19 C6 C25 C26 -55.9(5) . . . . ? O2 C6 C25 C30 4.7(5) . . . . ? C5 C6 C25 C30 -112.9(4) . . . . ? C19 C6 C25 C30 125.5(4) . . . . ? C30 C25 C26 C27 -1.8(6) . . . . ? C6 C25 C26 C27 179.7(4) . . . . ? C25 C26 C27 C28 0.8(7) . . . . ? C26 C27 C28 C29 0.1(7) . . . . ? C27 C28 C29 C30 0.0(7) . . . . ? C28 C29 C30 C25 -0.9(7) . . . . ? C26 C25 C30 C29 1.8(6) . . . . ? C6 C25 C30 C29 -179.6(4) . . . . ? O1A C1A C2A C3A -125.6(7) . . . . ? C6A C1A C2A C3A 51.4(9) . . . . ? C1A C2A C3A C4A -50.6(9) . . . . ? C2A C3A C4A C5A 54.8(8) . . . . ? C3A C4A C5A C7A 174.8(6) . . . . ? C3A C4A C5A C6A -57.7(7) . . . . ? O1A C1A C6A C5A 124.8(7) . . . . ? C2A C1A C6A C5A -52.1(8) . . . . ? C7A C5A C6A C1A -178.3(6) . . . . ? C4A C5A C6A C1A 54.0(7) . . . . ? O1B C1B C2B C3B 130.5(5) . . . . ? C6B C1B C2B C3B -50.2(6) . . . . ? C1B C2B C3B C7B 175.7(5) . . . . ? C1B C2B C3B C4B 51.5(6) . . . . ? C7B C3B C4B C5B 179.9(6) . . . . ? C2B C3B C4B C5B -57.1(7) . . . . ? C3B C4B C5B C6B 58.0(7) . . . . ? O1B C1B C6B C5B -130.2(5) . . . . ? C2B C1B C6B C5B 50.5(6) . . . . ? C4B C5B C6B C1B -52.8(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1A 0.976(2) 1.752(2) 2.717(4) 169(2) . O2 H2 O1B 0.964(2) 1.834(2) 2.769(4) 162.3(14) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.491 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.088 # Attachment '- 3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 885455' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol 3-methylcyclohexanone clathrate ; _chemical_name_common ;1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol 3- methylcyclohexanone clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H46 O4' _chemical_formula_weight 638.81 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2924(4) _cell_length_b 17.7601(11) _cell_length_c 16.1586(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.0470(10) _cell_angle_gamma 90.00 _cell_volume 1801.28(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19426 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 28.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19426 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.40 _reflns_number_total 4517 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _iucr_refine_instructions_details ; C2A, C2B, C3A, C3B, C5A, C5B, C6A, C6B, C7A and C7B were refined isotropically. Distance of O1-H1 was restrained to 0.960(5). ; _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^)+(0.0548P)^2^+0.8376P] 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 none _refine_ls_number_reflns 4517 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.46375(19) 0.43464(7) 0.35400(8) 0.0389(3) Uani 1 1 d D . . H1 H 0.499(4) 0.4870(4) 0.3563(14) 0.063(7) Uiso 1 1 d D . . C1 C 0.2393(3) 0.42648(9) 0.33856(9) 0.0308(3) Uani 1 1 d . . . C2 C 0.1307(3) 0.45752(9) 0.40937(10) 0.0356(4) Uani 1 1 d . . . C3 C 0.0474(3) 0.48408(9) 0.46688(10) 0.0368(4) Uani 1 1 d . . . C7 C 0.1624(3) 0.46603(8) 0.25721(9) 0.0304(3) Uani 1 1 d . . . C8 C -0.0340(3) 0.50082(10) 0.24721(11) 0.0405(4) Uani 1 1 d . . . H8 H -0.1240 0.5021 0.2920 0.049 Uiso 1 1 calc R . . C9 C -0.1004(4) 0.53396(11) 0.17179(13) 0.0514(5) Uani 1 1 d . . . H9 H -0.2359 0.5577 0.1651 0.062 Uiso 1 1 calc R . . C10 C 0.0298(4) 0.53250(11) 0.10677(12) 0.0537(5) Uani 1 1 d . . . H10 H -0.0151 0.5556 0.0555 0.064 Uiso 1 1 calc R . . C11 C 0.2248(4) 0.49758(11) 0.11621(12) 0.0524(5) Uani 1 1 d . . . H11 H 0.3137 0.4961 0.0711 0.063 Uiso 1 1 calc R . . C12 C 0.2925(3) 0.46449(10) 0.19123(10) 0.0402(4) Uani 1 1 d . . . H12 H 0.4280 0.4407 0.1975 0.048 Uiso 1 1 calc R . . C13 C 0.1932(3) 0.34172(9) 0.32986(9) 0.0331(4) Uani 1 1 d . . . C14 C -0.0055(3) 0.31329(10) 0.34496(11) 0.0412(4) Uani 1 1 d . . . H14 H -0.1134 0.3461 0.3619 0.049 Uiso 1 1 calc R . . C15 C -0.0473(4) 0.23680(11) 0.33537(13) 0.0508(5) Uani 1 1 d . . . H15 H -0.1835 0.2175 0.3461 0.061 Uiso 1 1 calc R . . C16 C 0.1085(4) 0.18872(11) 0.31020(13) 0.0537(5) Uani 1 1 d . . . H16 H 0.0800 0.1364 0.3038 0.064 Uiso 1 1 calc R . . C17 C 0.3052(4) 0.21708(10) 0.29450(12) 0.0495(5) Uani 1 1 d . . . H17 H 0.4121 0.1842 0.2769 0.059 Uiso 1 1 calc R . . C18 C 0.3490(3) 0.29348(10) 0.30420(11) 0.0402(4) Uani 1 1 d . . . H18 H 0.4853 0.3126 0.2933 0.048 Uiso 1 1 calc R . . O1A O 0.6007(2) 0.58298(7) 0.35816(9) 0.0532(4) Uani 1 1 d . A . C1A C 0.5730(3) 0.63849(11) 0.39858(14) 0.0510(5) Uani 1 1 d . . . C2A C 0.7396(4) 0.69846(15) 0.40832(18) 0.0415(6) Uiso 0.756(4) 1 d P A 1 H2A1 H 0.8512 0.6916 0.3611 0.050 Uiso 0.756(4) 1 calc PR A 1 H2A2 H 0.8263 0.6925 0.4681 0.050 Uiso 0.756(4) 1 calc PR A 1 C3A C 0.6403(4) 0.77788(13) 0.40130(16) 0.0389(6) Uiso 0.756(4) 1 d P A 1 H3A H 0.5613 0.7838 0.3401 0.047 Uiso 0.756(4) 1 calc PR A 1 C4A C 0.4710(3) 0.78472(11) 0.46582(12) 0.0472(5) Uani 0.756(4) 1 d P A 1 H4A1 H 0.5453 0.7765 0.5275 0.057 Uiso 0.756(4) 1 calc PR A 1 H4A2 H 0.4018 0.8404 0.4629 0.057 Uiso 0.756(4) 1 calc PR A 1 C5A C 0.2985(4) 0.72641(15) 0.44846(18) 0.0451(7) Uiso 0.756(4) 1 d P A 1 H5A1 H 0.2242 0.7349 0.3869 0.054 Uiso 0.756(4) 1 calc PR A 1 H5A2 H 0.1778 0.7329 0.4923 0.054 Uiso 0.756(4) 1 calc PR A 1 C6A C 0.3928(4) 0.64611(15) 0.45543(18) 0.0457(7) Uiso 0.756(4) 1 d P A 1 H6A1 H 0.4516 0.6353 0.5187 0.055 Uiso 0.756(4) 1 calc PR A 1 H6A2 H 0.2702 0.6053 0.4384 0.055 Uiso 0.756(4) 1 calc PR A 1 C7A C 0.8104(6) 0.8381(2) 0.4123(3) 0.0628(10) Uiso 0.756(4) 1 d P A 1 H7A1 H 0.7369 0.8930 0.4070 0.094 Uiso 0.756(4) 1 calc PR A 1 H7A2 H 0.9220 0.8318 0.3650 0.094 Uiso 0.756(4) 1 calc PR A 1 H7A3 H 0.8935 0.8323 0.4728 0.094 Uiso 0.756(4) 1 calc PR A 1 C2B C 0.6969(13) 0.7156(5) 0.3729(6) 0.043(2) Uiso 0.244(4) 1 d P A 2 H2B1 H 0.8582 0.7029 0.3588 0.052 Uiso 0.244(4) 1 calc PR A 2 H2B2 H 0.6153 0.7412 0.3189 0.052 Uiso 0.244(4) 1 calc PR A 2 C3B C 0.6970(14) 0.7691(5) 0.4475(6) 0.049(2) Uiso 0.244(4) 1 d P A 2 H3B H 0.7685 0.7386 0.5002 0.059 Uiso 0.244(4) 1 calc PR A 2 C4B C 0.4710(3) 0.78472(11) 0.46582(12) 0.0472(5) Uani 0.244(4) 1 d P A 2 H4B1 H 0.3895 0.8126 0.4134 0.057 Uiso 0.244(4) 1 calc PR A 2 H4B2 H 0.4688 0.8217 0.5188 0.057 Uiso 0.244(4) 1 calc PR A 2 C5B C 0.3497(13) 0.7079(5) 0.4847(6) 0.044(2) Uiso 0.244(4) 1 d P A 2 H5B1 H 0.4327 0.6794 0.5364 0.052 Uiso 0.244(4) 1 calc PR A 2 H5B2 H 0.1902 0.7204 0.5014 0.052 Uiso 0.244(4) 1 calc PR A 2 C6B C 0.3400(14) 0.6599(5) 0.4130(6) 0.048(2) Uiso 0.244(4) 1 d P A 2 H6B1 H 0.2674 0.6892 0.3597 0.057 Uiso 0.244(4) 1 calc PR A 2 H6B2 H 0.2474 0.6101 0.4237 0.057 Uiso 0.244(4) 1 calc PR A 2 C7B C 0.8229(12) 0.8404(4) 0.4411(6) 0.0322(17) Uiso 0.244(4) 1 d P A 2 H7B1 H 0.9847 0.8268 0.4283 0.048 Uiso 0.244(4) 1 calc PR A 2 H7B2 H 0.8233 0.8710 0.4988 0.048 Uiso 0.244(4) 1 calc PR A 2 H7B3 H 0.7514 0.8748 0.3914 0.048 Uiso 0.244(4) 1 calc PR A 2 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 0.0380(7) 0.0343(6) 0.0442(7) -0.0039(5) 0.0011(5) 0.0012(5) C1 0.0358(8) 0.0269(7) 0.0301(8) -0.0019(6) 0.0051(6) 0.0018(6) C2 0.0480(10) 0.0289(8) 0.0305(8) -0.0017(6) 0.0071(7) -0.0018(7) C3 0.0484(10) 0.0305(8) 0.0322(8) -0.0031(6) 0.0084(7) -0.0039(7) C7 0.0413(9) 0.0216(7) 0.0290(7) -0.0029(6) 0.0064(6) -0.0007(6) C8 0.0455(10) 0.0337(9) 0.0424(9) -0.0012(7) 0.0040(8) 0.0052(7) C9 0.0606(12) 0.0379(10) 0.0535(12) 0.0002(9) -0.0116(9) 0.0089(9) C10 0.0899(16) 0.0323(9) 0.0368(10) 0.0039(8) -0.0106(10) -0.0036(10) C11 0.0828(15) 0.0431(11) 0.0325(9) 0.0007(8) 0.0132(9) -0.0079(10) C12 0.0521(11) 0.0353(9) 0.0345(9) -0.0006(7) 0.0113(7) 0.0013(8) C13 0.0475(10) 0.0258(7) 0.0259(7) 0.0004(6) 0.0022(6) 0.0015(7) C14 0.0517(11) 0.0327(9) 0.0396(9) -0.0005(7) 0.0073(8) -0.0011(8) C15 0.0617(13) 0.0361(10) 0.0544(12) 0.0021(8) 0.0045(10) -0.0097(9) C16 0.0788(15) 0.0257(9) 0.0554(12) 0.0016(8) -0.0042(10) -0.0029(9) C17 0.0665(13) 0.0304(9) 0.0508(11) -0.0025(8) -0.0011(9) 0.0137(9) C18 0.0502(10) 0.0313(9) 0.0390(9) -0.0004(7) 0.0034(8) 0.0073(7) O1A 0.0550(8) 0.0367(7) 0.0681(9) -0.0109(6) 0.0051(7) 0.0046(6) C1A 0.0418(10) 0.0387(10) 0.0730(14) -0.0104(9) 0.0079(9) -0.0022(8) C4A 0.0543(11) 0.0380(10) 0.0497(11) -0.0068(8) 0.0073(9) 0.0047(8) C4B 0.0543(11) 0.0380(10) 0.0497(11) -0.0068(8) 0.0073(9) 0.0047(8) _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 C1 1.424(2) . ? O1 H1 0.957(5) . ? C1 C2 1.480(2) . ? C1 C13 1.538(2) . ? C1 C7 1.538(2) . ? C2 C3 1.196(2) . ? C3 C3 1.382(3) 3_566 ? C7 C8 1.381(2) . ? C7 C12 1.390(2) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 C11 1.373(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 C18 1.388(2) . ? C14 C15 1.390(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O1A C1A 1.202(2) . ? C1A C2A 1.495(3) . ? C1A C6A 1.515(3) . ? C1A C6B 1.548(9) . ? C1A C2B 1.644(8) . ? C2A C3A 1.543(4) . ? C2A H2A1 1.0800 . ? C2A H2A2 1.0800 . ? C3A C7A 1.514(4) . ? C3A C4A 1.547(3) . ? C3A H3A 1.0800 . ? C4A C5A 1.512(3) . ? C4A H4A1 1.0800 . ? C4A H4A2 1.0800 . ? C5A C6A 1.546(4) . ? C5A H5A1 1.0800 . ? C5A H5A2 1.0800 . ? C6A H6A1 1.0800 . ? C6A H6A2 1.0800 . ? C7A H7A1 1.0800 . ? C7A H7A2 1.0800 . ? C7A H7A3 1.0800 . ? C2B C3B 1.535(12) . ? C2B H2B1 1.0800 . ? C2B H2B2 1.0800 . ? C3B C7B 1.501(11) . ? C3B H3B 1.0800 . ? C5B C6B 1.436(12) . ? C5B H5B1 1.0800 . ? C5B H5B2 1.0800 . ? C6B H6B1 1.0800 . ? C6B H6B2 1.0800 . ? C7B H7B1 1.0800 . ? C7B H7B2 1.0800 . ? C7B H7B3 1.0800 . ? 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 C1 O1 H1 109.4(14) . . ? O1 C1 C2 109.46(13) . . ? O1 C1 C13 107.12(13) . . ? C2 C1 C13 109.92(13) . . ? O1 C1 C7 110.57(13) . . ? C2 C1 C7 110.86(13) . . ? C13 C1 C7 108.84(12) . . ? C3 C2 C1 178.14(18) . . ? C2 C3 C3 179.1(2) . 3_566 ? C8 C7 C12 119.33(16) . . ? C8 C7 C1 121.95(14) . . ? C12 C7 C1 118.69(15) . . ? C7 C8 C9 120.20(18) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.14(19) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.90(18) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.37(19) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.06(18) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C14 C13 C18 119.55(16) . . ? C14 C13 C1 120.50(15) . . ? C18 C13 C1 119.93(15) . . ? C13 C14 C15 120.16(18) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 119.58(18) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.66(19) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 119.81(18) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O1A C1A C2A 120.93(19) . . ? O1A C1A C6A 123.11(19) . . ? C2A C1A C6A 114.95(19) . . ? O1A C1A C6B 117.3(4) . . ? C2A C1A C6B 118.3(4) . . ? C6A C1A C6B 29.5(3) . . ? O1A C1A C2B 117.2(3) . . ? C2A C1A C2B 24.7(3) . . ? C6A C1A C2B 117.9(3) . . ? C6B C1A C2B 107.7(5) . . ? C1A C2A C3A 111.5(2) . . ? C1A C2A H2A1 109.3 . . ? C3A C2A H2A1 109.3 . . ? C1A C2A H2A2 109.3 . . ? C3A C2A H2A2 109.3 . . ? H2A1 C2A H2A2 108.0 . . ? C7A C3A C2A 110.9(2) . . ? C7A C3A C4A 112.3(2) . . ? C2A C3A C4A 108.5(2) . . ? C7A C3A H3A 108.3 . . ? C2A C3A H3A 108.3 . . ? C4A C3A H3A 108.3 . . ? C5A C4A C3A 109.92(18) . . ? C5A C4A H4A1 109.7 . . ? C3A C4A H4A1 109.7 . . ? C5A C4A H4A2 109.7 . . ? C3A C4A H4A2 109.7 . . ? H4A1 C4A H4A2 108.2 . . ? C4A C5A C6A 110.6(2) . . ? C4A C5A H5A1 109.5 . . ? C6A C5A H5A1 109.5 . . ? C4A C5A H5A2 109.5 . . ? C6A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 108.1 . . ? C1A C6A C5A 109.8(2) . . ? C1A C6A H6A1 109.7 . . ? C5A C6A H6A1 109.7 . . ? C1A C6A H6A2 109.7 . . ? C5A C6A H6A2 109.7 . . ? H6A1 C6A H6A2 108.2 . . ? C3A C7A H7A1 109.5 . . ? C3A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C3A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C3B C2B C1A 106.9(6) . . ? C3B C2B H2B1 110.3 . . ? C1A C2B H2B1 110.3 . . ? C3B C2B H2B2 110.3 . . ? C1A C2B H2B2 110.3 . . ? H2B1 C2B H2B2 108.6 . . ? C7B C3B C2B 116.0(7) . . ? C7B C3B H3B 106.6 . . ? C2B C3B H3B 106.6 . . ? C6B C5B H5B1 109.6 . . ? C6B C5B H5B2 109.6 . . ? H5B1 C5B H5B2 108.1 . . ? C5B C6B C1A 106.3(7) . . ? C5B C6B H6B1 110.5 . . ? C1A C6B H6B1 110.5 . . ? C5B C6B H6B2 110.5 . . ? C1A C6B H6B2 110.5 . . ? H6B1 C6B H6B2 108.7 . . ? C3B C7B H7B1 109.5 . . ? C3B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C3B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 33(6) . . . . ? C13 C1 C2 C3 150(6) . . . . ? C7 C1 C2 C3 -89(6) . . . . ? C1 C2 C3 C3 28(21) . . . 3_566 ? O1 C1 C7 C8 -145.83(15) . . . . ? C2 C1 C7 C8 -24.2(2) . . . . ? C13 C1 C7 C8 96.77(17) . . . . ? O1 C1 C7 C12 36.19(19) . . . . ? C2 C1 C7 C12 157.77(15) . . . . ? C13 C1 C7 C12 -81.21(18) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? C1 C7 C8 C9 -178.00(16) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C7 0.5(3) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? C1 C7 C12 C11 177.96(16) . . . . ? O1 C1 C13 C14 156.08(15) . . . . ? C2 C1 C13 C14 37.2(2) . . . . ? C7 C1 C13 C14 -84.35(18) . . . . ? O1 C1 C13 C18 -25.96(19) . . . . ? C2 C1 C13 C18 -144.80(16) . . . . ? C7 C1 C13 C18 93.61(17) . . . . ? C18 C13 C14 C15 0.8(3) . . . . ? C1 C13 C14 C15 178.72(16) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C14 C13 C18 C17 -0.5(3) . . . . ? C1 C13 C18 C17 -178.50(16) . . . . ? C16 C17 C18 C13 -0.1(3) . . . . ? O1A C1A C2A C3A 138.2(2) . . . . ? C6A C1A C2A C3A -53.0(3) . . . . ? C6B C1A C2A C3A -20.1(5) . . . . ? C2B C1A C2A C3A 49.8(7) . . . . ? C1A C2A C3A C7A 179.3(3) . . . . ? C1A C2A C3A C4A 55.5(3) . . . . ? C7A C3A C4A C5A 176.5(2) . . . . ? C2A C3A C4A C5A -60.5(3) . . . . ? C3A C4A C5A C6A 61.3(3) . . . . ? O1A C1A C6A C5A -139.8(2) . . . . ? C2A C1A C6A C5A 51.6(3) . . . . ? C6B C1A C6A C5A -52.2(7) . . . . ? C2B C1A C6A C5A 24.2(5) . . . . ? C4A C5A C6A C1A -55.2(3) . . . . ? O1A C1A C2B C3B -162.0(5) . . . . ? C2A C1A C2B C3B -56.5(7) . . . . ? C6A C1A C2B C3B 33.1(8) . . . . ? C6B C1A C2B C3B 63.2(8) . . . . ? C1A C2B C3B C7B 173.8(6) . . . . ? O1A C1A C6B C5B 159.1(5) . . . . ? C2A C1A C6B C5B -41.8(8) . . . . ? C6A C1A C6B C5B 49.5(7) . . . . ? C2B C1A C6B C5B -66.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1A 0.957(5) 1.819(6) 2.7711(18) 173(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.408 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.041