#------------------------------------------------------------------------------ #$Date: 2024-08-05 20:59:52 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293749 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571891.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1571891 loop_ _publ_author_name 'Nicolai, Stefano' 'Waser, Jérôme' _publ_section_title ; Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes. ; _journal_issue 28 _journal_name_full 'Chemical science' _journal_page_first 10823 _journal_page_last 10829 _journal_paper_doi 10.1039/d4sc02767a _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C14 H22 O2' _chemical_formula_sum 'C14 H22 O2' _chemical_formula_weight 222.31 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2023-12-05 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2023-12-05 deposited with the CCDC. 2024-06-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.6839(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.17394(11) _cell_length_b 8.78352(19) _cell_length_c 24.0129(5) _cell_measurement_reflns_used 3470 _cell_measurement_temperature 140.00(10) _cell_measurement_theta_max 75.7020 _cell_measurement_theta_min 5.3370 _cell_volume 1301.63(5) _computing_cell_refinement 'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))' _computing_data_reduction 'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 140.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2817 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -17.00 9.00 1.00 4.00 -- -40.91 105.00 -83.00 26 2 \w 33.00 65.00 1.00 4.00 -- 40.91-105.00 176.00 32 3 \w 71.00 96.00 1.00 16.00 -- 112.00-105.00 176.00 25 4 \w 106.00 161.00 1.00 16.00 -- 112.00 105.00 -83.00 55 5 \w -111.00 -86.00 1.00 4.00 -- -40.91 -38.00 90.00 25 6 \w -66.00 -17.00 1.00 4.00 -- -40.91 -38.00 90.00 49 7 \w 18.00 98.00 1.00 4.00 -- 40.91 38.00 120.00 80 8 \w 32.00 95.00 1.00 4.00 -- 40.91-125.00 30.00 63 9 \w 112.00 158.00 1.00 16.00 -- 112.00 77.00-150.00 46 10 \w 109.00 177.00 1.00 16.00 -- 112.00 77.00-120.00 68 11 \w 40.00 136.00 1.00 16.00 -- 112.00 -45.00-180.00 96 12 \w 129.00 175.00 1.00 16.00 -- 112.00 111.00 -60.00 46 13 \w 36.00 88.00 1.00 16.00 -- 112.00 -94.00-150.00 52 14 \w 65.00 91.00 1.00 16.00 -- 112.00-111.00 -30.00 26 15 \w 140.00 175.00 1.00 16.00 -- 112.00 45.00 0.00 35 16 \w 106.00 149.00 1.00 16.00 -- 112.00 77.00 -90.00 43 17 \w 72.00 106.00 1.00 16.00 -- 112.00 -94.00-120.00 34 18 \w 48.00 73.00 1.00 16.00 -- 112.00-111.00 60.00 25 19 \w 88.00 117.00 1.00 16.00 -- 112.00 45.00 0.00 29 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0878953000 _diffrn_orient_matrix_UB_12 -0.1168606000 _diffrn_orient_matrix_UB_13 -0.0415494000 _diffrn_orient_matrix_UB_21 0.0019760000 _diffrn_orient_matrix_UB_22 -0.1228121000 _diffrn_orient_matrix_UB_23 0.0458000000 _diffrn_orient_matrix_UB_31 -0.2335549000 _diffrn_orient_matrix_UB_32 -0.0450114000 _diffrn_orient_matrix_UB_33 -0.0172554000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 6239 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.945 _diffrn_reflns_theta_min 3.683 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.660 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear pale colourless' _exptl_crystal_density_diffrn 1.134 _exptl_crystal_description prism _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.616 _exptl_crystal_size_mid 0.091 _exptl_crystal_size_min 0.064 _refine_diff_density_max 0.266 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.0017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 2676 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0405 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.2480P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1068 _refine_ls_wR_factor_ref 0.1110 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2387 _reflns_number_total 2676 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02767a2.cif _cod_data_source_block ste-23-991 _cod_depositor_comments 'Adding full bibliography for 1571891--1571893.cif.' _cod_original_cell_volume 1301.63(4) _cod_database_code 1571891 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C14 H22 O2' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.964 _shelx_estimated_absorpt_t_min 0.717 _olex2_refinement_description ; ; _shelx_res_file ; TITL Ste-23-991 in P2(1)/c ste-23-991.res created by SHELXL-2019/3 at 15:44:43 on 05-Dec-2023 CELL 1.54184 6.17394 8.783518 24.012885 90 91.6839 90 ZERR 4 0.000112 0.000186 0.000483 0 0.0018 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 56 88 8 L.S. 10 PLAN 10 SIZE 0.616 0.091 0.064 TEMP -133 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.052500 0.248000 EXTI 0.001739 FVAR 8.50925 O1 3 0.169491 0.893369 0.702442 11.00000 0.04802 0.02735 = 0.04609 -0.00706 -0.00054 -0.00130 O2 3 0.694385 0.431642 0.602035 11.00000 0.02784 0.06104 = 0.06871 -0.03224 0.01507 -0.01080 C1 1 0.059717 0.685884 0.643804 11.00000 0.02551 0.02599 = 0.03654 -0.00187 -0.00313 0.00155 H1 2 -0.048681 0.608223 0.652706 11.00000 0.03172 C2 1 0.136600 0.757204 0.698459 11.00000 0.02416 0.02790 = 0.03607 -0.00468 0.00421 0.00218 C3 1 0.171606 0.653020 0.748046 11.00000 0.03674 0.03346 = 0.03114 -0.00431 0.00692 0.00098 H3A 2 0.232090 0.715524 0.778752 11.00000 0.03613 H3B 2 0.029918 0.616482 0.758351 11.00000 0.04878 C4 1 0.320782 0.517786 0.737148 11.00000 0.03797 0.03184 = 0.02627 0.00076 0.00233 0.00409 H4 2 0.368954 0.473399 0.773459 11.00000 0.04184 C5 1 0.236979 0.401599 0.692998 11.00000 0.03229 0.02519 = 0.03100 0.00135 0.00693 0.00070 H5A 2 0.294883 0.298610 0.700891 11.00000 0.03682 H5B 2 0.080374 0.393205 0.685951 11.00000 0.02936 C6 1 0.374229 0.485285 0.648949 11.00000 0.02272 0.02393 = 0.02743 -0.00154 0.00181 -0.00072 C7 1 0.508265 0.557286 0.698080 11.00000 0.02636 0.03110 = 0.03085 -0.00373 -0.00239 0.00244 H7A 2 0.545550 0.667925 0.694922 11.00000 0.03774 H7B 2 0.640095 0.496220 0.706479 11.00000 0.03518 C8 1 0.247801 0.605926 0.614602 11.00000 0.02871 0.02555 = 0.02662 -0.00033 0.00030 -0.00055 H8A 2 0.186855 0.559626 0.580201 11.00000 0.02691 H8B 2 0.355690 0.684358 0.602988 11.00000 0.03845 C9 1 -0.045566 0.803472 0.605028 11.00000 0.04840 0.03586 = 0.05238 -0.00065 -0.01599 0.01124 H9A 2 -0.169934 0.858506 0.623459 11.00000 0.06720 H9B 2 0.061854 0.883509 0.595678 11.00000 0.06342 H9C 2 -0.099747 0.755481 0.571248 11.00000 0.06504 C10 1 0.508200 0.393691 0.608638 11.00000 0.02439 0.02969 = 0.03428 -0.00485 0.00318 0.00004 C11 1 0.417784 0.255572 0.575972 11.00000 0.02751 0.02680 = 0.03108 -0.00495 0.00077 0.00120 C12 1 0.171357 0.240615 0.573504 11.00000 0.03020 0.04070 = 0.06715 -0.02088 -0.00270 -0.00317 H12A 2 0.130121 0.149746 0.551949 11.00000 0.04127 H12B 2 0.112310 0.231069 0.609513 11.00000 0.06421 H12C 2 0.101828 0.330813 0.555477 11.00000 0.08188 C13 1 0.515293 0.114487 0.604477 11.00000 0.05173 0.03047 = 0.05522 0.00015 -0.01209 0.00349 H13A 2 0.473593 0.023116 0.581871 11.00000 0.06072 H13B 2 0.676500 0.123401 0.609093 11.00000 0.06939 H13C 2 0.461611 0.099304 0.643247 11.00000 0.08145 C14 1 0.501270 0.265225 0.516558 11.00000 0.06135 0.05785 = 0.03212 -0.00822 0.00504 -0.01664 H14A 2 0.453409 0.175739 0.495643 11.00000 0.06124 H14B 2 0.436616 0.358620 0.498816 11.00000 0.07378 H14C 2 0.664376 0.274384 0.517172 11.00000 0.07405 HKLF 4 REM Ste-23-991 in P2(1)/c REM wR2 = 0.1110, GooF = S = 1.070, Restrained GooF = 1.070 for all data REM R1 = 0.0405 for 2387 Fo > 4sig(Fo) and 0.0448 for all 2676 data REM 234 parameters refined using 0 restraints END WGHT 0.0525 0.2480 REM Highest difference peak 0.266, deepest hole -0.220, 1-sigma level 0.035 Q1 1 0.4153 0.5450 0.7191 11.00000 0.05 0.27 Q2 1 0.4603 0.3239 0.5932 11.00000 0.05 0.23 Q3 1 0.3114 0.2456 0.5786 11.00000 0.05 0.21 Q4 1 0.1513 0.7010 0.7208 11.00000 0.05 0.21 Q5 1 0.7092 0.3606 0.6247 11.00000 0.05 0.20 Q6 1 0.2641 0.4574 0.7170 11.00000 0.05 0.19 Q7 1 0.2446 0.5850 0.7372 11.00000 0.05 0.19 Q8 1 0.4251 0.4362 0.6293 11.00000 0.05 0.18 Q9 1 0.2933 0.4468 0.6667 11.00000 0.05 0.18 Q10 1 0.4433 0.5236 0.6685 11.00000 0.05 0.18 ; _shelx_res_checksum 12742 _olex2_date_sample_data_collection 2023-12-05 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 2.476 _oxdiff_exptl_absorpt_empirical_full_min 0.480 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.16949(16) 0.89337(11) 0.70244(4) 0.0405(2) Uani 1 1 d . . . . . O2 O 0.69438(15) 0.43164(14) 0.60204(5) 0.0523(3) Uani 1 1 d . . . . . C1 C 0.05972(18) 0.68588(13) 0.64380(5) 0.0294(3) Uani 1 1 d . . . . . H1 H -0.049(2) 0.6082(18) 0.6527(6) 0.032(4) Uiso 1 1 d . . . . . C2 C 0.13660(18) 0.75720(13) 0.69846(5) 0.0293(3) Uani 1 1 d . . . . . C3 C 0.1716(2) 0.65302(15) 0.74805(5) 0.0337(3) Uani 1 1 d . . . . . H3A H 0.232(3) 0.7155(19) 0.7788(7) 0.036(4) Uiso 1 1 d . . . . . H3B H 0.030(3) 0.616(2) 0.7584(7) 0.049(5) Uiso 1 1 d . . . . . C4 C 0.3208(2) 0.51779(14) 0.73715(5) 0.0320(3) Uani 1 1 d . . . . . H4 H 0.369(3) 0.473(2) 0.7735(7) 0.042(4) Uiso 1 1 d . . . . . C5 C 0.23698(19) 0.40160(13) 0.69300(5) 0.0294(3) Uani 1 1 d . . . . . H5A H 0.295(3) 0.299(2) 0.7009(7) 0.037(4) Uiso 1 1 d . . . . . H5B H 0.080(2) 0.3932(17) 0.6860(6) 0.029(3) Uiso 1 1 d . . . . . C6 C 0.37423(16) 0.48529(12) 0.64895(4) 0.0247(2) Uani 1 1 d . . . . . C7 C 0.50827(18) 0.55729(14) 0.69808(5) 0.0295(3) Uani 1 1 d . . . . . H7A H 0.546(3) 0.6679(19) 0.6949(7) 0.038(4) Uiso 1 1 d . . . . . H7B H 0.640(3) 0.4962(18) 0.7065(6) 0.035(4) Uiso 1 1 d . . . . . C8 C 0.24780(18) 0.60593(13) 0.61460(5) 0.0270(3) Uani 1 1 d . . . . . H8A H 0.187(2) 0.5596(17) 0.5802(6) 0.027(3) Uiso 1 1 d . . . . . H8B H 0.356(3) 0.6844(19) 0.6030(7) 0.038(4) Uiso 1 1 d . . . . . C9 C -0.0456(3) 0.80347(17) 0.60503(7) 0.0459(4) Uani 1 1 d . . . . . H9A H -0.170(4) 0.859(3) 0.6235(9) 0.067(6) Uiso 1 1 d . . . . . H9B H 0.062(3) 0.884(3) 0.5957(9) 0.063(6) Uiso 1 1 d . . . . . H9C H -0.100(4) 0.755(2) 0.5712(9) 0.065(6) Uiso 1 1 d . . . . . C10 C 0.50820(18) 0.39369(14) 0.60864(5) 0.0294(3) Uani 1 1 d . . . . . C11 C 0.41778(18) 0.25557(13) 0.57597(5) 0.0285(3) Uani 1 1 d . . . . . C12 C 0.1714(2) 0.24062(18) 0.57350(8) 0.0461(4) Uani 1 1 d . . . . . H12A H 0.130(3) 0.150(2) 0.5519(7) 0.041(4) Uiso 1 1 d . . . . . H12B H 0.112(4) 0.231(2) 0.6095(9) 0.064(6) Uiso 1 1 d . . . . . H12C H 0.102(4) 0.331(3) 0.5555(10) 0.082(7) Uiso 1 1 d . . . . . C13 C 0.5153(3) 0.11449(16) 0.60448(7) 0.0461(4) Uani 1 1 d . . . . . H13A H 0.474(3) 0.023(2) 0.5819(9) 0.061(5) Uiso 1 1 d . . . . . H13B H 0.676(4) 0.123(3) 0.6091(9) 0.069(6) Uiso 1 1 d . . . . . H13C H 0.462(4) 0.099(3) 0.6432(11) 0.081(7) Uiso 1 1 d . . . . . C14 C 0.5013(3) 0.2652(2) 0.51656(6) 0.0504(4) Uani 1 1 d . . . . . H14A H 0.453(3) 0.176(2) 0.4956(9) 0.061(6) Uiso 1 1 d . . . . . H14B H 0.437(4) 0.359(3) 0.4988(10) 0.074(7) Uiso 1 1 d . . . . . H14C H 0.664(4) 0.274(3) 0.5172(9) 0.074(7) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0480(5) 0.0274(5) 0.0461(5) -0.0071(4) -0.0005(4) -0.0013(4) O2 0.0278(5) 0.0610(7) 0.0687(7) -0.0322(6) 0.0151(4) -0.0108(4) C1 0.0255(5) 0.0260(6) 0.0365(6) -0.0019(5) -0.0031(4) 0.0015(4) C2 0.0242(5) 0.0279(6) 0.0361(6) -0.0047(4) 0.0042(4) 0.0022(4) C3 0.0367(6) 0.0335(6) 0.0311(6) -0.0043(5) 0.0069(5) 0.0010(5) C4 0.0380(6) 0.0318(6) 0.0263(5) 0.0008(4) 0.0023(4) 0.0041(5) C5 0.0323(6) 0.0252(6) 0.0310(6) 0.0014(4) 0.0069(4) 0.0007(4) C6 0.0227(5) 0.0239(5) 0.0274(5) -0.0015(4) 0.0018(4) -0.0007(4) C7 0.0264(5) 0.0311(6) 0.0308(6) -0.0037(5) -0.0024(4) 0.0024(4) C8 0.0287(5) 0.0256(5) 0.0266(5) -0.0003(4) 0.0003(4) -0.0005(4) C9 0.0484(8) 0.0359(7) 0.0524(8) -0.0007(6) -0.0160(6) 0.0112(6) C10 0.0244(5) 0.0297(6) 0.0343(6) -0.0048(5) 0.0032(4) 0.0000(4) C11 0.0275(5) 0.0268(6) 0.0311(6) -0.0049(4) 0.0008(4) 0.0012(4) C12 0.0302(6) 0.0407(8) 0.0672(10) -0.0209(7) -0.0027(6) -0.0032(5) C13 0.0517(8) 0.0305(7) 0.0552(9) 0.0001(6) -0.0121(7) 0.0035(6) C14 0.0614(10) 0.0578(10) 0.0321(7) -0.0082(6) 0.0050(6) -0.0166(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 1 0.0445 -2 0 -1 0.2748 0 1 0 0.0429 -1 6 -1 0.0608 1 0 1 0.3170 0 1 -2 0.0380 -1 4 -10 0.0544 0 0 -1 0.0180 0 0 1 0.0457 0 -2 1 0.0466 0 -4 12 0.0418 0 -3 13 0.0437 0 2 15 0.0475 -1 1 14 0.1045 0 -4 -10 0.0349 1 -5 -7 0.0884 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 C2 C1 H1 107.2(9) . . ? C2 C1 C8 111.12(9) . . ? C2 C1 C9 111.45(10) . . ? C8 C1 H1 108.0(9) . . ? C9 C1 H1 108.8(9) . . ? C9 C1 C8 110.13(11) . . ? O1 C2 C1 121.40(11) . . ? O1 C2 C3 120.89(11) . . ? C3 C2 C1 117.71(10) . . ? C2 C3 H3A 107.1(10) . . ? C2 C3 H3B 107.0(11) . . ? C2 C3 C4 114.07(10) . . ? H3A C3 H3B 108.6(14) . . ? C4 C3 H3A 110.1(10) . . ? C4 C3 H3B 109.8(11) . . ? C3 C4 H4 108.7(10) . . ? C3 C4 C5 115.96(10) . . ? C3 C4 C7 113.17(10) . . ? C5 C4 H4 115.3(10) . . ? C5 C4 C7 88.49(9) . . ? C7 C4 H4 114.2(10) . . ? C4 C5 H5A 111.1(9) . . ? C4 C5 H5B 118.4(9) . . ? C4 C5 C6 88.65(9) . . ? H5A C5 H5B 108.3(13) . . ? C6 C5 H5A 111.1(9) . . ? C6 C5 H5B 118.2(9) . . ? C7 C6 C5 87.98(8) . . ? C8 C6 C5 114.24(9) . . ? C8 C6 C7 112.10(9) . . ? C10 C6 C5 119.92(10) . . ? C10 C6 C7 114.23(9) . . ? C10 C6 C8 107.42(9) . . ? C4 C7 C6 88.74(8) . . ? C4 C7 H7A 116.1(9) . . ? C4 C7 H7B 112.3(9) . . ? C6 C7 H7A 117.1(9) . . ? C6 C7 H7B 110.5(9) . . ? H7A C7 H7B 110.6(13) . . ? C1 C8 H8A 107.1(8) . . ? C1 C8 H8B 109.2(9) . . ? C6 C8 C1 116.48(9) . . ? C6 C8 H8A 109.9(8) . . ? C6 C8 H8B 106.9(9) . . ? H8A C8 H8B 106.9(12) . . ? C1 C9 H9A 111.7(13) . . ? C1 C9 H9B 109.9(12) . . ? C1 C9 H9C 110.4(13) . . ? H9A C9 H9B 106.1(17) . . ? H9A C9 H9C 109.0(18) . . ? H9B C9 H9C 109.6(17) . . ? O2 C10 C6 118.25(11) . . ? O2 C10 C11 118.75(10) . . ? C6 C10 C11 123.00(9) . . ? C12 C11 C10 115.68(10) . . ? C12 C11 C13 109.04(12) . . ? C12 C11 C14 109.30(12) . . ? C13 C11 C10 106.14(10) . . ? C13 C11 C14 108.80(12) . . ? C14 C11 C10 107.67(10) . . ? C11 C12 H12A 109.5(10) . . ? C11 C12 H12B 112.3(13) . . ? C11 C12 H12C 111.4(15) . . ? H12A C12 H12B 107.9(16) . . ? H12A C12 H12C 108.5(17) . . ? H12B C12 H12C 107.1(19) . . ? C11 C13 H13A 108.4(12) . . ? C11 C13 H13B 111.3(13) . . ? C11 C13 H13C 112.7(14) . . ? H13A C13 H13B 111.3(17) . . ? H13A C13 H13C 108.0(18) . . ? H13B C13 H13C 105.1(19) . . ? C11 C14 H14A 109.3(12) . . ? C11 C14 H14B 107.5(14) . . ? C11 C14 H14C 110.7(13) . . ? H14A C14 H14B 109.3(17) . . ? H14A C14 H14C 111.0(18) . . ? H14B C14 H14C 109.0(19) . . ? 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 C2 1.2164(15) . ? O2 C10 1.2117(15) . ? C1 H1 0.984(16) . ? C1 C2 1.5177(16) . ? C1 C8 1.5431(16) . ? C1 C9 1.5234(17) . ? C2 C3 1.5122(17) . ? C3 H3A 0.984(17) . ? C3 H3B 0.971(19) . ? C3 C4 1.5303(17) . ? C4 H4 0.993(17) . ? C4 C5 1.5495(16) . ? C4 C7 1.5505(17) . ? C5 H5A 0.989(17) . ? C5 H5B 0.979(15) . ? C5 C6 1.5588(15) . ? C6 C7 1.5554(14) . ? C6 C8 1.5410(15) . ? C6 C10 1.5217(15) . ? C7 H7A 1.002(17) . ? C7 H7B 0.991(16) . ? C8 H8A 0.985(15) . ? C8 H8B 1.003(17) . ? C9 H9A 1.02(2) . ? C9 H9B 1.00(2) . ? C9 H9C 0.97(2) . ? C10 C11 1.5404(15) . ? C11 C12 1.5265(17) . ? C11 C13 1.5305(18) . ? C11 C14 1.5335(19) . ? C12 H12A 0.981(18) . ? C12 H12B 0.95(2) . ? C12 H12C 0.99(3) . ? C13 H13A 1.00(2) . ? C13 H13B 1.00(2) . ? C13 H13C 1.01(3) . ? C14 H14A 0.97(2) . ? C14 H14B 1.00(2) . ? C14 H14C 1.01(2) . ? 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 C2 C3 C4 -126.61(13) . . . . ? O2 C10 C11 C12 -163.70(14) . . . . ? O2 C10 C11 C13 75.23(16) . . . . ? O2 C10 C11 C14 -41.15(17) . . . . ? C1 C2 C3 C4 53.28(15) . . . . ? C2 C1 C8 C6 54.88(13) . . . . ? C2 C3 C4 C5 -64.31(14) . . . . ? C2 C3 C4 C7 35.85(14) . . . . ? C3 C4 C5 C6 96.53(11) . . . . ? C3 C4 C7 C6 -99.05(10) . . . . ? C4 C5 C6 C7 18.56(8) . . . . ? C4 C5 C6 C8 -94.82(10) . . . . ? C4 C5 C6 C10 135.54(10) . . . . ? C5 C4 C7 C6 18.66(8) . . . . ? C5 C6 C7 C4 -18.55(8) . . . . ? C5 C6 C8 C1 29.82(13) . . . . ? C5 C6 C10 O2 -132.84(13) . . . . ? C5 C6 C10 C11 47.22(15) . . . . ? C6 C10 C11 C12 16.24(17) . . . . ? C6 C10 C11 C13 -104.83(13) . . . . ? C6 C10 C11 C14 138.79(13) . . . . ? C7 C4 C5 C6 -18.62(8) . . . . ? C7 C6 C8 C1 -68.29(12) . . . . ? C7 C6 C10 O2 -30.45(17) . . . . ? C7 C6 C10 C11 149.61(11) . . . . ? C8 C1 C2 O1 102.28(13) . . . . ? C8 C1 C2 C3 -77.61(13) . . . . ? C8 C6 C7 C4 96.86(10) . . . . ? C8 C6 C10 O2 94.55(14) . . . . ? C8 C6 C10 C11 -85.39(13) . . . . ? C9 C1 C2 O1 -20.96(17) . . . . ? C9 C1 C2 C3 159.15(12) . . . . ? C9 C1 C8 C6 178.88(10) . . . . ? C10 C6 C7 C4 -140.66(10) . . . . ? C10 C6 C8 C1 165.43(9) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0006 1.0000 0.9983 -0.1583 -0.0771 -0.0624 -2.0010 0.0004 -1.0015 -0.1343 -0.0499 0.4846 0.0005 0.9999 -0.0013 -0.1168 -0.1229 -0.0451 -0.8353 5.5650 -0.8743 -0.6874 -0.7251 -0.0403 1.0005 -0.0002 1.0006 0.0464 0.0478 -0.2509 0.0003 0.9997 -2.0004 -0.0337 -0.2144 -0.0106 -0.8855 4.0693 -10.2589 -0.1271 -0.9714 0.2007 -0.0001 -0.0001 -0.9996 0.0415 -0.0458 0.0173 0.0001 0.0001 0.9996 -0.0415 0.0458 -0.0173 -0.0009 -1.9998 1.0021 0.1920 0.2915 0.0729 0.0334 -3.5973 12.0860 -0.0788 0.9954 -0.0544 -0.1950 -3.1811 12.9318 -0.1827 0.9826 -0.0344 -0.2382 1.5075 15.0176 -0.8211 0.5022 -0.2713 -1.3973 1.1121 14.4365 -0.8526 0.5219 0.0272 -0.0853 -4.3441 -10.0647 0.9183 0.0724 0.3891 0.8709 -4.9350 -7.1172 0.9490 0.2818 0.1415