# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2019 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_JF2849FMI _database_code_depnum_ccdc_archive 'CCDC 1916890' loop_ _audit_author_name _audit_author_address 'James Fettinger' ;University of California, Davis United States of America ; _audit_update_record ; 2019-05-18 deposited with the CCDC. 2019-11-11 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 O2' _chemical_formula_sum 'C28 H24 O2' _chemical_formula_weight 392.47 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5034(17) _cell_length_b 10.6505(19) _cell_length_c 21.889(4) _cell_angle_alpha 96.945(3) _cell_angle_beta 102.069(3) _cell_angle_gamma 99.440(3) _cell_volume 2109.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9975 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 30.52 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_F_000 832 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.781 _exptl_crystal_size_mid 0.652 _exptl_crystal_size_min 0.320 _exptl_absorpt_coefficient_mu 0.076 _shelx_estimated_absorpt_T_min 0.943 _shelx_estimated_absorpt_T_max 0.976 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8536 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details 'SADABS 2016/2 (Sheldrick, 2016)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19292 _diffrn_reflns_av_unetI/netI 0.0159 _diffrn_reflns_av_R_equivalents 0.0110 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.928 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 9689 _reflns_number_gt 8901 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. A colorless block with approximate orthogonal dimensions 0.320 x 0.652 x 0.781mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD system at --183\%C(90K). Indexing of the unit cell used a random set of reflections collected from three series of 0.5\% wide omega-scans, 5 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Six omega-scan data frame series were collected [MoKa] with 0.3\% wide scans, 15 seconds per frame and 606 frames collected per series at varying f angles (f=0\%, 60\%, 120\%, 180\%, 240\%, 300\%). The crystal to detector distance was 5.15cm, thus providing a complete sphere of data to 2thetamax=61.09\%. ; _computing_data_collection 'Apex2 (2014.9-1) (Bruker, 2014)' _computing_cell_refinement 'SAINT (8.38a) (Bruker, 2017)' _computing_data_reduction 'SAINT (8.38a) (Bruker, 2017)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Structural determination and Refinement: All crystallographic calculations were performed on an Intel Xeon E5-1620v2 at 3.70GHz an eight core processor and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint(1) and absorption using Blessing?s method and merged as incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the probable space group and set up the initial files. System symmetry, lack of systematic absences and intensity statistics indicated the centrosymmetric triclinic space group P-1 (no. 2). The structure was determined by direct methods with a majority of the non-hydrogen atoms for the two molecules being located directly using the program XT(5). The structure was refined with XL(6). The data collected were merged for least squares refinement to 9689 unique data [R(int)=0.0110]. Hydrogen atoms were initially calculated and placed in idealized locations and then allowed to refine freely during the final cycles of refinement. All non-hydrogen atoms were refined anisotropically. The final structure was refined to convergence with R(F)=3.89%, wR(F2)=9.59%, GOF=1.033 for all 8901 unique reflections [R(F)=3.61, wR(F2)=9.32% for those 8901 data with Fo > 4sigma(Fo). The final difference-Fourier map was featureless indicating that the structure is both correct and complete. An empirical correction for extinction was also attempted and found to be less than one sigma and therefore not applied. 1. Bruker (2017) APEX3 (Version 2017.3) and (2017) SAINT (Version 8.38a). Bruker AXS Inc., Madison, Wisconsin, USA. 2. An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38. 3. Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector Absorption Correction? Universit\"at G\"ottingen: G\"ottingen, Germany. 4. Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA. 5. Sheldrick, G. M., (2014) SHELXT, Universit\"at G\"ottingen: G\"ottingen, Germany. Structure determination program. Private communication. 6. Sheldrick, G. M., (2018). SHELXL2018/3. Universit\"at G\"ottingen: G\"ottingen, Germany. Acknowledgment: We thank the National Science Foundation (Grant 1531193) for the Dual source X-ray diffractometer. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.7054P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 9689 _refine_ls_number_parameters 733 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _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_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 C1 C 0.89477(10) 0.94027(9) 0.75550(4) 0.01520(17) Uani 1 1 d . . . . . H1 H 1.0011(13) 0.9697(11) 0.7770(5) 0.013(3) Uiso 1 1 d . . . . . O1 O 0.83984(7) 0.82434(6) 0.77731(3) 0.01597(14) Uani 1 1 d . . . . . C2 C 0.81425(10) 1.04809(9) 0.77467(4) 0.01476(17) Uani 1 1 d . . . . . H2 H 0.8697(13) 1.1302(11) 0.7669(5) 0.013(3) Uiso 1 1 d . . . . . C3 C 0.81864(10) 1.05815(9) 0.84487(4) 0.01512(17) Uani 1 1 d . . . . . C4 C 0.84420(10) 0.95601(9) 0.87768(4) 0.01556(18) Uani 1 1 d . . . . . C5 C 0.88407(10) 0.83635(9) 0.84472(4) 0.01557(18) Uani 1 1 d . . . . . H5 H 0.9931(13) 0.8474(11) 0.8570(5) 0.015(3) Uiso 1 1 d . . . . . C6 C 0.84161(11) 0.96757(9) 0.94180(5) 0.01894(19) Uani 1 1 d . . . . . H6 H 0.8590(14) 0.8965(13) 0.9650(6) 0.022(3) Uiso 1 1 d . . . . . C7 C 0.81678(11) 1.08034(10) 0.97336(5) 0.02039(19) Uani 1 1 d . . . . . H7 H 0.8146(14) 1.0885(12) 1.0178(6) 0.023(3) Uiso 1 1 d . . . . . C8 C 0.79338(11) 1.18269(9) 0.94092(5) 0.01973(19) Uani 1 1 d . . . . . H8 H 0.7755(15) 1.2622(13) 0.9631(6) 0.026(3) Uiso 1 1 d . . . . . C9 C 0.79280(10) 1.17076(9) 0.87703(5) 0.01745(18) Uani 1 1 d . . . . . H9 H 0.7731(14) 1.2400(12) 0.8530(6) 0.021(3) Uiso 1 1 d . . . . . C10 C 0.88013(10) 0.91010(9) 0.68504(4) 0.01572(18) Uani 1 1 d . . . . . C11 C 0.97411(11) 0.98573(10) 0.65677(5) 0.01950(19) Uani 1 1 d . . . . . H11 H 1.0508(15) 1.0556(13) 0.6833(6) 0.025(3) Uiso 1 1 d . . . . . C12 C 0.96347(11) 0.96154(10) 0.59211(5) 0.0220(2) Uani 1 1 d . . . . . H12 H 1.0293(16) 1.0128(14) 0.5722(7) 0.032(4) Uiso 1 1 d . . . . . C13 C 0.85874(11) 0.85877(10) 0.55463(5) 0.02016(19) Uani 1 1 d . . . . . O13 O 0.85951(9) 0.84007(8) 0.49139(4) 0.03015(18) Uani 1 1 d . . . . . C14 C 0.76301(11) 0.78291(10) 0.58168(5) 0.02032(19) Uani 1 1 d . . . . . H14 H 0.6884(15) 0.7121(13) 0.5560(6) 0.028(3) Uiso 1 1 d . . . . . C15 C 0.77370(11) 0.81013(9) 0.64673(5) 0.01849(19) Uani 1 1 d . . . . . H15 H 0.7065(15) 0.7567(13) 0.6657(6) 0.027(3) Uiso 1 1 d . . . . . C16 C 0.77865(14) 0.72102(12) 0.45435(5) 0.0314(3) Uani 1 1 d . . . . . H16A H 0.8147(17) 0.6487(15) 0.4734(7) 0.037(4) Uiso 1 1 d . . . . . H16B H 0.7986(18) 0.7222(15) 0.4116(8) 0.043(4) Uiso 1 1 d . . . . . H16C H 0.6720(17) 0.7143(14) 0.4510(7) 0.037(4) Uiso 1 1 d . . . . . C17 C 0.65736(10) 1.02994(9) 0.73575(4) 0.01552(18) Uani 1 1 d . . . . . C18 C 0.62215(11) 1.11036(11) 0.69161(5) 0.0228(2) Uani 1 1 d . . . . . H18 H 0.6978(16) 1.1777(14) 0.6870(7) 0.031(3) Uiso 1 1 d . . . . . C19 C 0.47947(12) 1.09476(12) 0.65515(5) 0.0290(2) Uani 1 1 d . . . . . H19 H 0.4570(17) 1.1540(15) 0.6250(7) 0.038(4) Uiso 1 1 d . . . . . C20 C 0.37032(12) 0.99829(11) 0.66237(5) 0.0259(2) Uani 1 1 d . . . . . H20 H 0.2696(16) 0.9876(13) 0.6367(7) 0.031(4) Uiso 1 1 d . . . . . C21 C 0.40369(11) 0.91761(10) 0.70627(5) 0.0225(2) Uani 1 1 d . . . . . H21 H 0.3274(16) 0.8498(14) 0.7116(7) 0.030(3) Uiso 1 1 d . . . . . C22 C 0.54570(11) 0.93372(9) 0.74302(5) 0.01913(19) Uani 1 1 d . . . . . H22 H 0.5673(15) 0.8773(13) 0.7751(6) 0.025(3) Uiso 1 1 d . . . . . C23 C 0.81683(10) 0.71171(9) 0.86311(4) 0.01579(18) Uani 1 1 d . . . . . C24 C 0.67310(11) 0.65022(10) 0.83410(5) 0.0215(2) Uani 1 1 d . . . . . H24 H 0.6157(15) 0.6858(13) 0.8007(6) 0.028(3) Uiso 1 1 d . . . . . C25 C 0.61092(12) 0.53811(10) 0.85285(5) 0.0246(2) Uani 1 1 d . . . . . H25 H 0.5079(17) 0.4952(14) 0.8323(7) 0.036(4) Uiso 1 1 d . . . . . C26 C 0.69091(12) 0.48630(10) 0.90086(5) 0.0218(2) Uani 1 1 d . . . . . H26 H 0.6441(16) 0.4095(14) 0.9145(7) 0.031(3) Uiso 1 1 d . . . . . C27 C 0.83452(12) 0.54602(10) 0.92942(5) 0.0233(2) Uani 1 1 d . . . . . H27 H 0.8927(15) 0.5100(13) 0.9634(7) 0.031(4) Uiso 1 1 d . . . . . C28 C 0.89792(11) 0.65777(9) 0.91033(5) 0.02001(19) Uani 1 1 d . . . . . H28 H 1.0005(15) 0.6990(13) 0.9294(6) 0.028(3) Uiso 1 1 d . . . . . C31 C 1.03115(10) 0.53256(9) 0.24186(5) 0.01681(18) Uani 1 1 d . . . . . H31 H 1.0949(13) 0.5198(11) 0.2118(6) 0.016(3) Uiso 1 1 d . . . . . O31 O 0.95089(7) 0.63035(6) 0.22422(3) 0.01804(14) Uani 1 1 d . . . . . C32 C 0.92291(10) 0.40323(9) 0.23558(5) 0.01618(18) Uani 1 1 d . . . . . H32 H 0.9830(14) 0.3349(12) 0.2382(6) 0.021(3) Uiso 1 1 d . . . . . C33 C 0.81633(10) 0.37696(9) 0.17097(4) 0.01642(18) Uani 1 1 d . . . . . C34 C 0.79771(10) 0.47457(9) 0.13434(4) 0.01639(18) Uani 1 1 d . . . . . C35 C 0.88596(10) 0.61159(9) 0.15807(5) 0.01721(18) Uani 1 1 d . . . . . H35 H 0.9660(14) 0.6261(12) 0.1346(6) 0.024(3) Uiso 1 1 d . . . . . C36 C 0.69784(11) 0.44656(10) 0.07521(5) 0.02016(19) Uani 1 1 d . . . . . H36 H 0.6857(15) 0.5152(13) 0.0497(6) 0.027(3) Uiso 1 1 d . . . . . C37 C 0.61447(12) 0.32349(10) 0.05301(5) 0.0228(2) Uani 1 1 d . . . . . H37 H 0.5442(16) 0.3059(14) 0.0119(7) 0.034(4) Uiso 1 1 d . . . . . C38 C 0.63122(12) 0.22625(10) 0.08971(5) 0.0227(2) Uani 1 1 d . . . . . H38 H 0.5712(15) 0.1398(14) 0.0744(6) 0.028(3) Uiso 1 1 d . . . . . C39 C 0.73153(11) 0.25287(9) 0.14789(5) 0.01946(19) Uani 1 1 d . . . . . H39 H 0.7426(14) 0.1856(13) 0.1740(6) 0.022(3) Uiso 1 1 d . . . . . C40 C 1.12443(10) 0.58119(9) 0.30788(5) 0.01725(18) Uani 1 1 d . . . . . C41 C 1.25232(11) 0.53477(10) 0.32886(5) 0.0211(2) Uani 1 1 d . . . . . H41 H 1.2781(15) 0.4682(14) 0.3002(7) 0.029(3) Uiso 1 1 d . . . . . C42 C 1.34108(11) 0.58101(10) 0.38886(5) 0.0230(2) Uani 1 1 d . . . . . H42 H 1.4328(16) 0.5516(14) 0.4036(7) 0.034(4) Uiso 1 1 d . . . . . C43 C 1.30518(11) 0.67725(10) 0.42860(5) 0.02018(19) Uani 1 1 d . . . . . O43 O 1.40581(9) 0.72336(8) 0.48505(4) 0.02621(17) Uani 1 1 d . . . . . C44 C 1.17555(11) 0.72133(10) 0.40934(5) 0.0208(2) Uani 1 1 d . . . . . H44 H 1.1479(15) 0.7883(13) 0.4370(6) 0.026(3) Uiso 1 1 d . . . . . C45 C 1.08602(11) 0.67224(10) 0.34933(5) 0.01959(19) Uani 1 1 d . . . . . H45 H 0.9979(15) 0.7037(13) 0.3351(6) 0.027(3) Uiso 1 1 d . . . . . C46 C 1.38984(14) 0.84047(11) 0.52014(6) 0.0293(2) Uani 1 1 d . . . . . H46A H 1.3832(16) 0.9101(15) 0.4928(7) 0.037(4) Uiso 1 1 d . . . . . H46B H 1.4763(17) 0.8632(14) 0.5553(7) 0.038(4) Uiso 1 1 d . . . . . H46C H 1.2998(17) 0.8279(14) 0.5368(7) 0.034(4) Uiso 1 1 d . . . . . C47 C 0.84429(10) 0.40088(9) 0.28944(4) 0.01624(18) Uani 1 1 d . . . . . C48 C 0.90850(11) 0.36295(10) 0.34611(5) 0.02029(19) Uani 1 1 d . . . . . H48 H 1.0010(16) 0.3364(13) 0.3506(6) 0.029(3) Uiso 1 1 d . . . . . C49 C 0.83977(12) 0.36403(10) 0.39635(5) 0.0244(2) Uani 1 1 d . . . . . H49 H 0.8873(16) 0.3359(14) 0.4355(7) 0.032(4) Uiso 1 1 d . . . . . C50 C 0.70458(13) 0.40131(11) 0.39057(5) 0.0256(2) Uani 1 1 d . . . . . H50 H 0.6552(16) 0.4006(14) 0.4254(7) 0.032(4) Uiso 1 1 d . . . . . C51 C 0.63963(12) 0.43818(11) 0.33441(5) 0.0245(2) Uani 1 1 d . . . . . H51 H 0.5438(17) 0.4637(14) 0.3288(7) 0.035(4) Uiso 1 1 d . . . . . C52 C 0.70912(11) 0.43852(10) 0.28432(5) 0.01947(19) Uani 1 1 d . . . . . H52 H 0.6616(14) 0.4645(12) 0.2445(6) 0.022(3) Uiso 1 1 d . . . . . C53 C 0.79148(10) 0.71222(9) 0.14816(5) 0.01740(18) Uani 1 1 d . . . . . C54 C 0.70406(11) 0.73761(9) 0.19039(5) 0.01967(19) Uani 1 1 d . . . . . H54 H 0.7106(13) 0.6940(12) 0.2281(6) 0.019(3) Uiso 1 1 d . . . . . C55 C 0.60938(12) 0.82349(10) 0.17991(5) 0.0232(2) Uani 1 1 d . . . . . H55 H 0.5487(15) 0.8406(13) 0.2096(7) 0.029(3) Uiso 1 1 d . . . . . C56 C 0.60159(12) 0.88551(10) 0.12719(6) 0.0253(2) Uani 1 1 d . . . . . H56 H 0.5338(16) 0.9452(14) 0.1191(7) 0.031(4) Uiso 1 1 d . . . . . C57 C 0.69014(12) 0.86261(10) 0.08559(5) 0.0260(2) Uani 1 1 d . . . . . H57 H 0.6860(16) 0.9063(14) 0.0489(7) 0.032(4) Uiso 1 1 d . . . . . C58 C 0.78568(12) 0.77666(10) 0.09616(5) 0.0225(2) Uani 1 1 d . . . . . H58 H 0.8486(15) 0.7614(13) 0.0672(6) 0.027(3) 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 C1 0.0141(4) 0.0151(4) 0.0176(4) 0.0037(3) 0.0054(3) 0.0030(3) O1 0.0198(3) 0.0140(3) 0.0153(3) 0.0033(2) 0.0057(3) 0.0040(2) C2 0.0144(4) 0.0130(4) 0.0175(4) 0.0034(3) 0.0049(3) 0.0025(3) C3 0.0121(4) 0.0149(4) 0.0181(4) 0.0023(3) 0.0037(3) 0.0016(3) C4 0.0139(4) 0.0141(4) 0.0178(4) 0.0008(3) 0.0032(3) 0.0022(3) C5 0.0163(4) 0.0152(4) 0.0157(4) 0.0028(3) 0.0036(3) 0.0047(3) C6 0.0224(5) 0.0161(4) 0.0183(4) 0.0033(4) 0.0041(4) 0.0042(4) C7 0.0245(5) 0.0191(5) 0.0171(4) 0.0006(4) 0.0052(4) 0.0042(4) C8 0.0208(5) 0.0159(4) 0.0217(5) -0.0009(4) 0.0051(4) 0.0044(4) C9 0.0165(4) 0.0143(4) 0.0217(5) 0.0030(3) 0.0043(3) 0.0032(3) C10 0.0147(4) 0.0165(4) 0.0182(4) 0.0038(3) 0.0058(3) 0.0059(3) C11 0.0180(4) 0.0187(4) 0.0216(5) 0.0018(4) 0.0068(4) 0.0014(4) C12 0.0211(5) 0.0230(5) 0.0229(5) 0.0058(4) 0.0096(4) 0.0000(4) C13 0.0216(5) 0.0230(5) 0.0170(4) 0.0043(4) 0.0061(4) 0.0045(4) O13 0.0365(4) 0.0325(4) 0.0174(4) 0.0006(3) 0.0098(3) -0.0068(3) C14 0.0188(5) 0.0203(5) 0.0198(5) 0.0031(4) 0.0029(4) 0.0005(4) C15 0.0169(4) 0.0193(4) 0.0201(5) 0.0056(4) 0.0058(4) 0.0020(4) C16 0.0341(6) 0.0352(6) 0.0196(5) -0.0029(4) 0.0066(4) -0.0031(5) C17 0.0153(4) 0.0156(4) 0.0166(4) 0.0010(3) 0.0054(3) 0.0047(3) C18 0.0200(5) 0.0270(5) 0.0246(5) 0.0113(4) 0.0076(4) 0.0053(4) C19 0.0247(5) 0.0410(6) 0.0256(5) 0.0151(5) 0.0055(4) 0.0121(5) C20 0.0172(5) 0.0372(6) 0.0220(5) -0.0006(4) 0.0024(4) 0.0079(4) C21 0.0165(5) 0.0202(5) 0.0289(5) -0.0031(4) 0.0067(4) 0.0020(4) C22 0.0183(4) 0.0144(4) 0.0258(5) 0.0032(4) 0.0067(4) 0.0044(3) C23 0.0191(4) 0.0135(4) 0.0162(4) 0.0014(3) 0.0059(3) 0.0058(3) C24 0.0202(5) 0.0192(5) 0.0250(5) 0.0085(4) 0.0015(4) 0.0049(4) C25 0.0205(5) 0.0207(5) 0.0316(5) 0.0087(4) 0.0025(4) 0.0021(4) C26 0.0265(5) 0.0169(4) 0.0248(5) 0.0075(4) 0.0084(4) 0.0057(4) C27 0.0283(5) 0.0212(5) 0.0212(5) 0.0080(4) 0.0024(4) 0.0082(4) C28 0.0207(5) 0.0180(4) 0.0200(5) 0.0029(4) 0.0009(4) 0.0050(4) C31 0.0137(4) 0.0163(4) 0.0211(5) 0.0024(3) 0.0055(3) 0.0034(3) O31 0.0184(3) 0.0148(3) 0.0204(3) 0.0023(3) 0.0032(3) 0.0038(3) C32 0.0147(4) 0.0144(4) 0.0202(4) 0.0022(3) 0.0050(3) 0.0040(3) C33 0.0154(4) 0.0166(4) 0.0184(4) 0.0005(3) 0.0071(3) 0.0041(3) C34 0.0163(4) 0.0163(4) 0.0181(4) 0.0007(3) 0.0080(3) 0.0039(3) C35 0.0170(4) 0.0167(4) 0.0190(4) 0.0033(3) 0.0068(4) 0.0029(3) C36 0.0244(5) 0.0196(5) 0.0180(4) 0.0026(4) 0.0072(4) 0.0062(4) C37 0.0254(5) 0.0226(5) 0.0184(5) -0.0017(4) 0.0032(4) 0.0050(4) C38 0.0248(5) 0.0176(5) 0.0235(5) -0.0023(4) 0.0060(4) 0.0017(4) C39 0.0215(5) 0.0160(4) 0.0217(5) 0.0019(4) 0.0073(4) 0.0040(4) C40 0.0148(4) 0.0162(4) 0.0205(5) 0.0026(3) 0.0059(3) 0.0003(3) C41 0.0175(4) 0.0214(5) 0.0241(5) -0.0005(4) 0.0060(4) 0.0049(4) C42 0.0178(5) 0.0264(5) 0.0248(5) 0.0020(4) 0.0042(4) 0.0068(4) C43 0.0196(5) 0.0217(5) 0.0183(4) 0.0027(4) 0.0056(4) 0.0002(4) O43 0.0254(4) 0.0303(4) 0.0198(4) -0.0019(3) 0.0021(3) 0.0048(3) C44 0.0222(5) 0.0200(5) 0.0217(5) 0.0015(4) 0.0096(4) 0.0040(4) C45 0.0172(4) 0.0198(5) 0.0233(5) 0.0033(4) 0.0074(4) 0.0045(4) C46 0.0310(6) 0.0273(6) 0.0249(5) -0.0042(4) 0.0062(5) -0.0007(5) C47 0.0158(4) 0.0128(4) 0.0193(4) 0.0016(3) 0.0044(3) 0.0010(3) C48 0.0164(4) 0.0193(4) 0.0242(5) 0.0058(4) 0.0024(4) 0.0019(4) C49 0.0263(5) 0.0246(5) 0.0202(5) 0.0062(4) 0.0029(4) 0.0005(4) C50 0.0302(5) 0.0254(5) 0.0225(5) 0.0023(4) 0.0122(4) 0.0030(4) C51 0.0229(5) 0.0273(5) 0.0266(5) 0.0034(4) 0.0105(4) 0.0087(4) C52 0.0192(5) 0.0200(5) 0.0205(5) 0.0039(4) 0.0054(4) 0.0062(4) C53 0.0168(4) 0.0131(4) 0.0210(5) 0.0016(3) 0.0040(4) 0.0009(3) C54 0.0217(5) 0.0154(4) 0.0220(5) 0.0022(4) 0.0064(4) 0.0027(4) C55 0.0233(5) 0.0178(5) 0.0293(5) 0.0007(4) 0.0088(4) 0.0049(4) C56 0.0227(5) 0.0164(5) 0.0364(6) 0.0056(4) 0.0044(4) 0.0051(4) C57 0.0274(5) 0.0216(5) 0.0299(5) 0.0113(4) 0.0052(4) 0.0041(4) C58 0.0235(5) 0.0211(5) 0.0248(5) 0.0067(4) 0.0088(4) 0.0036(4) _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 C1 O1 1.4353(11) . ? C1 C10 1.5090(13) . ? C1 C2 1.5447(12) . ? C1 H1 1.002(12) . ? O1 C5 1.4309(11) . ? C2 C3 1.5187(13) . ? C2 C17 1.5234(13) . ? C2 H2 0.997(12) . ? C3 C9 1.3996(13) . ? C3 C4 1.4001(13) . ? C4 C6 1.3999(13) . ? C4 C5 1.5292(12) . ? C5 C23 1.5135(13) . ? C5 H5 0.998(12) . ? C6 C7 1.3913(14) . ? C6 H6 0.979(13) . ? C7 C8 1.3937(14) . ? C7 H7 0.970(13) . ? C8 C9 1.3876(14) . ? C8 H8 0.982(14) . ? C9 H9 0.977(13) . ? C10 C15 1.3914(14) . ? C10 C11 1.3946(13) . ? C11 C12 1.3868(14) . ? C11 H11 0.982(14) . ? C12 C13 1.3949(15) . ? C12 H12 0.969(15) . ? C13 O13 1.3760(12) . ? C13 C14 1.3896(14) . ? O13 C16 1.4237(14) . ? C14 C15 1.3971(14) . ? C14 H14 0.971(14) . ? C15 H15 0.976(14) . ? C16 H16A 0.995(16) . ? C16 H16B 0.995(16) . ? C16 H16C 0.991(16) . ? C17 C18 1.3921(14) . ? C17 C22 1.3981(13) . ? C18 C19 1.3944(15) . ? C18 H18 0.960(15) . ? C19 C20 1.3837(17) . ? C19 H19 0.983(15) . ? C20 C21 1.3869(16) . ? C20 H20 0.984(14) . ? C21 C22 1.3909(14) . ? C21 H21 0.971(15) . ? C22 H22 0.990(13) . ? C23 C24 1.3933(14) . ? C23 C28 1.3956(13) . ? C24 C25 1.3899(14) . ? C24 H24 0.972(14) . ? C25 C26 1.3894(15) . ? C25 H25 0.995(16) . ? C26 C27 1.3858(16) . ? C26 H26 0.976(15) . ? C27 C28 1.3944(15) . ? C27 H27 0.987(14) . ? C28 H28 0.981(14) . ? C31 O31 1.4319(11) . ? C31 C40 1.5085(13) . ? C31 C32 1.5506(13) . ? C31 H31 0.995(12) . ? O31 C35 1.4260(12) . ? C32 C33 1.5219(13) . ? C32 C47 1.5226(13) . ? C32 H32 0.996(13) . ? C33 C34 1.3990(13) . ? C33 C39 1.4037(13) . ? C34 C36 1.4019(14) . ? C34 C35 1.5283(13) . ? C35 C53 1.5141(13) . ? C35 H35 1.006(13) . ? C36 C37 1.3879(14) . ? C36 H36 0.979(14) . ? C37 C38 1.3946(15) . ? C37 H37 0.978(15) . ? C38 C39 1.3884(15) . ? C38 H38 0.979(14) . ? C39 H39 0.975(13) . ? C40 C45 1.3923(13) . ? C40 C41 1.3968(14) . ? C41 C42 1.3867(15) . ? C41 H41 0.985(14) . ? C42 C43 1.3954(14) . ? C42 H42 0.979(15) . ? C43 O43 1.3738(12) . ? C43 C44 1.3914(14) . ? O43 C46 1.4309(14) . ? C44 C45 1.3941(14) . ? C44 H44 0.984(14) . ? C45 H45 0.959(14) . ? C46 H46A 1.008(15) . ? C46 H46B 0.976(16) . ? C46 H46C 0.994(15) . ? C47 C52 1.3939(13) . ? C47 C48 1.3999(14) . ? C48 C49 1.3914(15) . ? C48 H48 0.956(14) . ? C49 C50 1.3914(16) . ? C49 H49 0.986(14) . ? C50 C51 1.3876(16) . ? C50 H50 0.975(15) . ? C51 C52 1.3931(14) . ? C51 H51 0.981(15) . ? C52 H52 0.988(13) . ? C53 C58 1.3946(14) . ? C53 C54 1.3972(14) . ? C54 C55 1.3904(14) . ? C54 H54 0.990(12) . ? C55 C56 1.3923(16) . ? C55 H55 0.974(14) . ? C56 C57 1.3894(16) . ? C56 H56 0.982(14) . ? C57 C58 1.3971(15) . ? C57 H57 0.972(15) . ? C58 H58 0.976(14) . ? 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 O1 C1 C10 108.54(7) . . ? O1 C1 C2 109.94(7) . . ? C10 C1 C2 113.46(7) . . ? O1 C1 H1 108.5(7) . . ? C10 C1 H1 109.0(7) . . ? C2 C1 H1 107.3(7) . . ? C5 O1 C1 111.57(7) . . ? C3 C2 C17 111.05(7) . . ? C3 C2 C1 109.03(7) . . ? C17 C2 C1 113.56(8) . . ? C3 C2 H2 108.8(7) . . ? C17 C2 H2 107.3(7) . . ? C1 C2 H2 106.8(7) . . ? C9 C3 C4 119.36(9) . . ? C9 C3 C2 119.20(8) . . ? C4 C3 C2 121.42(8) . . ? C6 C4 C3 119.49(9) . . ? C6 C4 C5 120.28(8) . . ? C3 C4 C5 120.12(8) . . ? O1 C5 C23 107.55(7) . . ? O1 C5 C4 111.53(7) . . ? C23 C5 C4 113.59(8) . . ? O1 C5 H5 108.3(7) . . ? C23 C5 H5 108.8(7) . . ? C4 C5 H5 106.9(7) . . ? C7 C6 C4 120.60(9) . . ? C7 C6 H6 119.4(8) . . ? C4 C6 H6 120.0(8) . . ? C6 C7 C8 119.90(9) . . ? C6 C7 H7 120.8(8) . . ? C8 C7 H7 119.3(8) . . ? C9 C8 C7 119.74(9) . . ? C9 C8 H8 120.2(8) . . ? C7 C8 H8 120.0(8) . . ? C8 C9 C3 120.88(9) . . ? C8 C9 H9 121.1(7) . . ? C3 C9 H9 118.0(7) . . ? C15 C10 C11 118.46(9) . . ? C15 C10 C1 122.13(8) . . ? C11 C10 C1 119.40(8) . . ? C12 C11 C10 121.10(9) . . ? C12 C11 H11 119.6(8) . . ? C10 C11 H11 119.3(8) . . ? C11 C12 C13 119.71(9) . . ? C11 C12 H12 121.6(9) . . ? C13 C12 H12 118.7(9) . . ? O13 C13 C14 124.36(9) . . ? O13 C13 C12 115.47(9) . . ? C14 C13 C12 120.17(9) . . ? C13 O13 C16 117.11(8) . . ? C13 C14 C15 119.29(9) . . ? C13 C14 H14 120.9(8) . . ? C15 C14 H14 119.8(8) . . ? C10 C15 C14 121.23(9) . . ? C10 C15 H15 119.5(8) . . ? C14 C15 H15 119.2(8) . . ? O13 C16 H16A 109.1(9) . . ? O13 C16 H16B 105.5(9) . . ? H16A C16 H16B 110.7(13) . . ? O13 C16 H16C 111.1(9) . . ? H16A C16 H16C 111.2(13) . . ? H16B C16 H16C 109.1(12) . . ? C18 C17 C22 118.31(9) . . ? C18 C17 C2 120.00(8) . . ? C22 C17 C2 121.70(8) . . ? C17 C18 C19 120.91(10) . . ? C17 C18 H18 118.7(9) . . ? C19 C18 H18 120.3(8) . . ? C20 C19 C18 120.18(10) . . ? C20 C19 H19 120.5(9) . . ? C18 C19 H19 119.3(9) . . ? C19 C20 C21 119.56(10) . . ? C19 C20 H20 120.1(8) . . ? C21 C20 H20 120.4(8) . . ? C20 C21 C22 120.32(10) . . ? C20 C21 H21 119.9(8) . . ? C22 C21 H21 119.8(8) . . ? C21 C22 C17 120.71(9) . . ? C21 C22 H22 119.5(8) . . ? C17 C22 H22 119.8(8) . . ? C24 C23 C28 119.02(9) . . ? C24 C23 C5 120.83(8) . . ? C28 C23 C5 120.15(9) . . ? C25 C24 C23 120.31(9) . . ? C25 C24 H24 119.6(8) . . ? C23 C24 H24 120.0(8) . . ? C26 C25 C24 120.50(10) . . ? C26 C25 H25 119.6(9) . . ? C24 C25 H25 119.9(9) . . ? C27 C26 C25 119.54(10) . . ? C27 C26 H26 121.1(8) . . ? C25 C26 H26 119.3(8) . . ? C26 C27 C28 120.18(9) . . ? C26 C27 H27 120.4(8) . . ? C28 C27 H27 119.5(8) . . ? C27 C28 C23 120.43(9) . . ? C27 C28 H28 120.6(8) . . ? C23 C28 H28 118.9(8) . . ? O31 C31 C40 107.15(7) . . ? O31 C31 C32 109.62(7) . . ? C40 C31 C32 113.98(8) . . ? O31 C31 H31 108.4(7) . . ? C40 C31 H31 109.9(7) . . ? C32 C31 H31 107.6(7) . . ? C35 O31 C31 112.89(7) . . ? C33 C32 C47 112.25(8) . . ? C33 C32 C31 109.10(8) . . ? C47 C32 C31 112.31(8) . . ? C33 C32 H32 108.9(7) . . ? C47 C32 H32 107.5(7) . . ? C31 C32 H32 106.6(7) . . ? C34 C33 C39 118.79(9) . . ? C34 C33 C32 121.58(8) . . ? C39 C33 C32 119.61(9) . . ? C33 C34 C36 119.83(9) . . ? C33 C34 C35 120.58(8) . . ? C36 C34 C35 119.60(8) . . ? O31 C35 C53 106.56(7) . . ? O31 C35 C34 111.45(8) . . ? C53 C35 C34 112.15(8) . . ? O31 C35 H35 108.9(7) . . ? C53 C35 H35 109.5(7) . . ? C34 C35 H35 108.3(7) . . ? C37 C36 C34 120.78(9) . . ? C37 C36 H36 119.8(8) . . ? C34 C36 H36 119.4(8) . . ? C36 C37 C38 119.61(10) . . ? C36 C37 H37 119.7(9) . . ? C38 C37 H37 120.7(9) . . ? C39 C38 C37 119.90(9) . . ? C39 C38 H38 120.5(8) . . ? C37 C38 H38 119.6(8) . . ? C38 C39 C33 121.08(9) . . ? C38 C39 H39 120.2(8) . . ? C33 C39 H39 118.7(8) . . ? C45 C40 C41 118.39(9) . . ? C45 C40 C31 121.45(9) . . ? C41 C40 C31 120.16(9) . . ? C42 C41 C40 120.78(9) . . ? C42 C41 H41 120.6(8) . . ? C40 C41 H41 118.6(8) . . ? C41 C42 C43 120.12(9) . . ? C41 C42 H42 121.7(9) . . ? C43 C42 H42 118.1(9) . . ? O43 C43 C44 124.60(9) . . ? O43 C43 C42 115.60(9) . . ? C44 C43 C42 119.80(9) . . ? C43 O43 C46 116.81(9) . . ? C43 C44 C45 119.36(9) . . ? C43 C44 H44 120.8(8) . . ? C45 C44 H44 119.8(8) . . ? C40 C45 C44 121.41(9) . . ? C40 C45 H45 118.4(8) . . ? C44 C45 H45 120.1(8) . . ? O43 C46 H46A 111.1(9) . . ? O43 C46 H46B 105.0(9) . . ? H46A C46 H46B 112.0(12) . . ? O43 C46 H46C 111.5(9) . . ? H46A C46 H46C 107.7(12) . . ? H46B C46 H46C 109.6(12) . . ? C52 C47 C48 118.40(9) . . ? C52 C47 C32 121.32(9) . . ? C48 C47 C32 120.27(9) . . ? C49 C48 C47 120.81(10) . . ? C49 C48 H48 119.4(8) . . ? C47 C48 H48 119.8(8) . . ? C50 C49 C48 120.24(10) . . ? C50 C49 H49 120.9(8) . . ? C48 C49 H49 118.9(8) . . ? C51 C50 C49 119.34(10) . . ? C51 C50 H50 120.2(8) . . ? C49 C50 H50 120.5(8) . . ? C50 C51 C52 120.47(10) . . ? C50 C51 H51 121.1(9) . . ? C52 C51 H51 118.4(9) . . ? C51 C52 C47 120.74(9) . . ? C51 C52 H52 119.7(7) . . ? C47 C52 H52 119.5(7) . . ? C58 C53 C54 119.23(9) . . ? C58 C53 C35 121.14(9) . . ? C54 C53 C35 119.59(9) . . ? C55 C54 C53 120.52(9) . . ? C55 C54 H54 120.3(7) . . ? C53 C54 H54 119.2(7) . . ? C54 C55 C56 120.05(10) . . ? C54 C55 H55 120.0(8) . . ? C56 C55 H55 120.0(8) . . ? C57 C56 C55 119.78(10) . . ? C57 C56 H56 119.7(8) . . ? C55 C56 H56 120.5(8) . . ? C56 C57 C58 120.24(10) . . ? C56 C57 H57 120.2(9) . . ? C58 C57 H57 119.6(9) . . ? C53 C58 C57 120.15(10) . . ? C53 C58 H58 119.7(8) . . ? C57 C58 H58 120.1(8) . . ? 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 C10 C1 O1 C5 164.91(7) . . . . ? C2 C1 O1 C5 -70.46(9) . . . . ? O1 C1 C2 C3 50.72(10) . . . . ? C10 C1 C2 C3 172.47(7) . . . . ? O1 C1 C2 C17 -73.67(10) . . . . ? C10 C1 C2 C17 48.08(10) . . . . ? C17 C2 C3 C9 -72.94(10) . . . . ? C1 C2 C3 C9 161.19(8) . . . . ? C17 C2 C3 C4 105.38(10) . . . . ? C1 C2 C3 C4 -20.48(11) . . . . ? C9 C3 C4 C6 0.82(14) . . . . ? C2 C3 C4 C6 -177.51(8) . . . . ? C9 C3 C4 C5 -175.38(8) . . . . ? C2 C3 C4 C5 6.30(13) . . . . ? C1 O1 C5 C23 178.09(7) . . . . ? C1 O1 C5 C4 52.93(10) . . . . ? C6 C4 C5 O1 162.95(8) . . . . ? C3 C4 C5 O1 -20.88(12) . . . . ? C6 C4 C5 C23 41.22(12) . . . . ? C3 C4 C5 C23 -142.61(9) . . . . ? C3 C4 C6 C7 -1.27(14) . . . . ? C5 C4 C6 C7 174.93(9) . . . . ? C4 C6 C7 C8 0.37(15) . . . . ? C6 C7 C8 C9 0.97(15) . . . . ? C7 C8 C9 C3 -1.42(15) . . . . ? C4 C3 C9 C8 0.52(14) . . . . ? C2 C3 C9 C8 178.88(9) . . . . ? O1 C1 C10 C15 26.90(12) . . . . ? C2 C1 C10 C15 -95.62(11) . . . . ? O1 C1 C10 C11 -154.26(8) . . . . ? C2 C1 C10 C11 83.22(11) . . . . ? C15 C10 C11 C12 -0.71(15) . . . . ? C1 C10 C11 C12 -179.59(9) . . . . ? C10 C11 C12 C13 -1.00(16) . . . . ? C11 C12 C13 O13 -178.11(9) . . . . ? C11 C12 C13 C14 1.61(16) . . . . ? C14 C13 O13 C16 -13.47(16) . . . . ? C12 C13 O13 C16 166.24(10) . . . . ? O13 C13 C14 C15 179.20(10) . . . . ? C12 C13 C14 C15 -0.50(15) . . . . ? C11 C10 C15 C14 1.85(14) . . . . ? C1 C10 C15 C14 -179.30(9) . . . . ? C13 C14 C15 C10 -1.25(15) . . . . ? C3 C2 C17 C18 128.24(9) . . . . ? C1 C2 C17 C18 -108.46(10) . . . . ? C3 C2 C17 C22 -51.71(11) . . . . ? C1 C2 C17 C22 71.59(11) . . . . ? C22 C17 C18 C19 -0.54(15) . . . . ? C2 C17 C18 C19 179.50(10) . . . . ? C17 C18 C19 C20 -0.11(18) . . . . ? C18 C19 C20 C21 0.25(17) . . . . ? C19 C20 C21 C22 0.26(16) . . . . ? C20 C21 C22 C17 -0.93(15) . . . . ? C18 C17 C22 C21 1.05(14) . . . . ? C2 C17 C22 C21 -178.99(9) . . . . ? O1 C5 C23 C24 -41.37(11) . . . . ? C4 C5 C23 C24 82.55(11) . . . . ? O1 C5 C23 C28 139.62(9) . . . . ? C4 C5 C23 C28 -96.45(10) . . . . ? C28 C23 C24 C25 1.16(15) . . . . ? C5 C23 C24 C25 -177.86(9) . . . . ? C23 C24 C25 C26 0.28(17) . . . . ? C24 C25 C26 C27 -1.05(17) . . . . ? C25 C26 C27 C28 0.38(16) . . . . ? C26 C27 C28 C23 1.08(16) . . . . ? C24 C23 C28 C27 -1.84(15) . . . . ? C5 C23 C28 C27 177.19(9) . . . . ? C40 C31 O31 C35 165.67(7) . . . . ? C32 C31 O31 C35 -70.17(9) . . . . ? O31 C31 C32 C33 49.41(10) . . . . ? C40 C31 C32 C33 169.48(8) . . . . ? O31 C31 C32 C47 -75.70(10) . . . . ? C40 C31 C32 C47 44.37(11) . . . . ? C47 C32 C33 C34 108.11(10) . . . . ? C31 C32 C33 C34 -17.03(12) . . . . ? C47 C32 C33 C39 -70.26(11) . . . . ? C31 C32 C33 C39 164.60(8) . . . . ? C39 C33 C34 C36 -1.28(13) . . . . ? C32 C33 C34 C36 -179.66(8) . . . . ? C39 C33 C34 C35 179.04(8) . . . . ? C32 C33 C34 C35 0.66(13) . . . . ? C31 O31 C35 C53 173.54(7) . . . . ? C31 O31 C35 C34 50.90(10) . . . . ? C33 C34 C35 O31 -15.77(12) . . . . ? C36 C34 C35 O31 164.55(8) . . . . ? C33 C34 C35 C53 -135.15(9) . . . . ? C36 C34 C35 C53 45.17(12) . . . . ? C33 C34 C36 C37 1.43(14) . . . . ? C35 C34 C36 C37 -178.89(9) . . . . ? C34 C36 C37 C38 -0.58(15) . . . . ? C36 C37 C38 C39 -0.39(16) . . . . ? C37 C38 C39 C33 0.52(15) . . . . ? C34 C33 C39 C38 0.32(14) . . . . ? C32 C33 C39 C38 178.73(9) . . . . ? O31 C31 C40 C45 24.83(12) . . . . ? C32 C31 C40 C45 -96.62(11) . . . . ? O31 C31 C40 C41 -155.36(9) . . . . ? C32 C31 C40 C41 83.19(11) . . . . ? C45 C40 C41 C42 -1.84(15) . . . . ? C31 C40 C41 C42 178.35(9) . . . . ? C40 C41 C42 C43 -1.54(16) . . . . ? C41 C42 C43 O43 -175.21(9) . . . . ? C41 C42 C43 C44 3.79(16) . . . . ? C44 C43 O43 C46 -12.78(15) . . . . ? C42 C43 O43 C46 166.16(10) . . . . ? O43 C43 C44 C45 176.30(9) . . . . ? C42 C43 C44 C45 -2.60(15) . . . . ? C41 C40 C45 C44 3.05(15) . . . . ? C31 C40 C45 C44 -177.15(9) . . . . ? C43 C44 C45 C40 -0.84(15) . . . . ? C33 C32 C47 C52 -31.26(12) . . . . ? C31 C32 C47 C52 92.10(11) . . . . ? C33 C32 C47 C48 150.04(9) . . . . ? C31 C32 C47 C48 -86.59(11) . . . . ? C52 C47 C48 C49 -0.64(14) . . . . ? C32 C47 C48 C49 178.09(9) . . . . ? C47 C48 C49 C50 0.91(16) . . . . ? C48 C49 C50 C51 -0.43(16) . . . . ? C49 C50 C51 C52 -0.29(17) . . . . ? C50 C51 C52 C47 0.56(16) . . . . ? C48 C47 C52 C51 -0.09(15) . . . . ? C32 C47 C52 C51 -178.81(9) . . . . ? O31 C35 C53 C58 139.94(9) . . . . ? C34 C35 C53 C58 -97.85(11) . . . . ? O31 C35 C53 C54 -42.58(11) . . . . ? C34 C35 C53 C54 79.62(11) . . . . ? C58 C53 C54 C55 1.71(15) . . . . ? C35 C53 C54 C55 -175.81(9) . . . . ? C53 C54 C55 C56 -0.32(15) . . . . ? C54 C55 C56 C57 -0.87(16) . . . . ? C55 C56 C57 C58 0.67(17) . . . . ? C54 C53 C58 C57 -1.91(15) . . . . ? C35 C53 C58 C57 175.58(9) . . . . ? C56 C57 C58 C53 0.73(16) . . . . ? 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 _geom_hbond_publ_flag C12 H12 O13 0.969(15) 2.472(15) 3.4189(13) 165.6(12) 2_776 yes _refine_diff_density_max 0.377 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.038 _shelx_res_file ; TITL JF2849Fmi in P-1 FINAL ALL DATA MERGE-I 17MAY2019 JF2849FMI.res created by SHELXL-2018/3 at 11:14:26 on 17-May-2019 CELL 0.71073 9.5034 10.6505 21.8886 96.9449 102.0691 99.4402 ZERR 4.00 0.0017 0.0019 0.0039 0.0026 0.0025 0.0025 LATT 1 SFAC C H O UNIT 112 96 8 L.S. 9 OMIT -5 55.00 HTAB WPDB -2 CONF EQIV $1 -x+2, -y+2, -z+1 HTAB C12 O13_$1 EQIV $2 -x+2, -y+1, -z+1 HTAB C32 O1_$2 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.320 0.652 0.781 TEMP -183. REM 1SIGMA EXTI 0.000629 WGHT 0.048700 0.705400 FVAR 0.19389 C1 1 0.894770 0.940269 0.755502 11.00000 0.01408 0.01509 = 0.01755 0.00368 0.00542 0.00303 REM AFIX 13 H1 2 1.001119 0.969738 0.777048 11.00000 0.01349 REM AFIX 0 O1 3 0.839843 0.824341 0.777312 11.00000 0.01985 0.01396 = 0.01530 0.00329 0.00569 0.00400 C2 1 0.814254 1.048086 0.774672 11.00000 0.01445 0.01304 = 0.01751 0.00341 0.00493 0.00254 REM AFIX 13 H2 2 0.869693 1.130199 0.766907 11.00000 0.01325 REM AFIX 0 C3 1 0.818641 1.058150 0.844875 11.00000 0.01211 0.01485 = 0.01805 0.00229 0.00370 0.00165 C4 1 0.844199 0.956013 0.877675 11.00000 0.01394 0.01410 = 0.01780 0.00085 0.00324 0.00218 C5 1 0.884067 0.836348 0.844722 11.00000 0.01634 0.01525 = 0.01569 0.00282 0.00355 0.00473 REM AFIX 13 H5 2 0.993096 0.847437 0.857020 11.00000 0.01469 REM AFIX 0 C6 1 0.841605 0.967573 0.941801 11.00000 0.02238 0.01610 = 0.01834 0.00334 0.00408 0.00422 REM AFIX 43 H6 2 0.859040 0.896495 0.965044 11.00000 0.02237 REM AFIX 0 C7 1 0.816777 1.080339 0.973356 11.00000 0.02454 0.01907 = 0.01710 0.00057 0.00520 0.00421 REM AFIX 43 H7 2 0.814624 1.088473 1.017760 11.00000 0.02267 REM AFIX 0 C8 1 0.793380 1.182693 0.940923 11.00000 0.02084 0.01593 = 0.02175 -0.00094 0.00511 0.00443 REM AFIX 43 H8 2 0.775536 1.262231 0.963060 11.00000 0.02611 REM AFIX 0 C9 1 0.792801 1.170756 0.877033 11.00000 0.01646 0.01426 = 0.02169 0.00303 0.00433 0.00321 REM AFIX 43 H9 2 0.773065 1.240038 0.853025 11.00000 0.02088 REM AFIX 0 C10 1 0.880132 0.910102 0.685042 11.00000 0.01470 0.01646 = 0.01815 0.00377 0.00584 0.00593 C11 1 0.974109 0.985727 0.656772 11.00000 0.01803 0.01871 = 0.02162 0.00178 0.00685 0.00140 REM AFIX 43 H11 2 1.050780 1.055644 0.683320 11.00000 0.02532 REM AFIX 0 C12 1 0.963471 0.961542 0.592112 11.00000 0.02109 0.02299 = 0.02287 0.00578 0.00958 0.00002 REM AFIX 43 H12 2 1.029345 1.012787 0.572227 11.00000 0.03198 REM AFIX 0 C13 1 0.858741 0.858773 0.554627 11.00000 0.02157 0.02298 = 0.01701 0.00433 0.00614 0.00451 O13 3 0.859514 0.840071 0.491395 11.00000 0.03646 0.03254 = 0.01737 0.00057 0.00975 -0.00679 C14 1 0.763011 0.782907 0.581680 11.00000 0.01882 0.02035 = 0.01984 0.00308 0.00286 0.00052 REM AFIX 43 H14 2 0.688447 0.712135 0.555954 11.00000 0.02774 REM AFIX 0 C15 1 0.773698 0.810125 0.646733 11.00000 0.01688 0.01927 = 0.02011 0.00561 0.00584 0.00202 REM AFIX 43 H15 2 0.706494 0.756713 0.665696 11.00000 0.02668 REM AFIX 0 C16 1 0.778650 0.721020 0.454353 11.00000 0.03410 0.03521 = 0.01962 -0.00289 0.00658 -0.00314 REM AFIX 137 H16A 2 0.814676 0.648667 0.473401 11.00000 0.03720 H16B 2 0.798551 0.722198 0.411564 11.00000 0.04325 H16C 2 0.671979 0.714303 0.450953 11.00000 0.03696 REM AFIX 0 C17 1 0.657359 1.029938 0.735748 11.00000 0.01525 0.01565 = 0.01659 0.00102 0.00537 0.00472 C18 1 0.622146 1.110357 0.691607 11.00000 0.02002 0.02699 = 0.02456 0.01127 0.00761 0.00530 REM AFIX 43 H18 2 0.697846 1.177692 0.686972 11.00000 0.03095 REM AFIX 0 C19 1 0.479473 1.094755 0.655154 11.00000 0.02471 0.04096 = 0.02557 0.01511 0.00547 0.01215 REM AFIX 43 H19 2 0.456990 1.154006 0.624956 11.00000 0.03770 REM AFIX 0 C20 1 0.370325 0.998288 0.662371 11.00000 0.01720 0.03716 = 0.02200 -0.00055 0.00243 0.00794 REM AFIX 43 H20 2 0.269626 0.987568 0.636667 11.00000 0.03121 REM AFIX 0 C21 1 0.403689 0.917610 0.706265 11.00000 0.01651 0.02019 = 0.02889 -0.00310 0.00666 0.00198 REM AFIX 43 H21 2 0.327422 0.849837 0.711568 11.00000 0.03008 REM AFIX 0 C22 1 0.545704 0.933716 0.743016 11.00000 0.01831 0.01440 = 0.02584 0.00323 0.00674 0.00444 REM AFIX 43 H22 2 0.567321 0.877277 0.775139 11.00000 0.02471 REM AFIX 0 C23 1 0.816834 0.711714 0.863111 11.00000 0.01910 0.01351 = 0.01622 0.00142 0.00586 0.00581 C24 1 0.673098 0.650221 0.834101 11.00000 0.02025 0.01918 = 0.02502 0.00850 0.00147 0.00487 REM AFIX 43 H24 2 0.615661 0.685778 0.800654 11.00000 0.02804 REM AFIX 0 C25 1 0.610917 0.538114 0.852850 11.00000 0.02050 0.02068 = 0.03157 0.00873 0.00250 0.00212 REM AFIX 43 H25 2 0.507850 0.495232 0.832297 11.00000 0.03643 REM AFIX 0 C26 1 0.690906 0.486303 0.900861 11.00000 0.02646 0.01686 = 0.02475 0.00754 0.00840 0.00567 REM AFIX 43 H26 2 0.644124 0.409481 0.914534 11.00000 0.03107 REM AFIX 0 C27 1 0.834523 0.546024 0.929421 11.00000 0.02831 0.02119 = 0.02123 0.00801 0.00237 0.00825 REM AFIX 43 H27 2 0.892714 0.509970 0.963414 11.00000 0.03089 REM AFIX 0 C28 1 0.897917 0.657768 0.910325 11.00000 0.02073 0.01797 = 0.01999 0.00291 0.00091 0.00499 REM AFIX 43 H28 2 1.000476 0.699013 0.929355 11.00000 0.02773 REM AFIX 0 C31 1 1.031154 0.532556 0.241856 11.00000 0.01367 0.01629 = 0.02113 0.00235 0.00552 0.00340 REM AFIX 13 H31 2 1.094897 0.519783 0.211816 11.00000 0.01592 REM AFIX 0 O31 3 0.950891 0.630349 0.224222 11.00000 0.01838 0.01478 = 0.02038 0.00225 0.00315 0.00376 C32 1 0.922911 0.403233 0.235577 11.00000 0.01466 0.01437 = 0.02016 0.00223 0.00497 0.00396 REM AFIX 13 H32 2 0.982955 0.334863 0.238206 11.00000 0.02098 REM AFIX 0 C33 1 0.816334 0.376964 0.170971 11.00000 0.01543 0.01657 = 0.01841 0.00051 0.00708 0.00407 C34 1 0.797714 0.474572 0.134345 11.00000 0.01632 0.01630 = 0.01807 0.00070 0.00800 0.00393 C35 1 0.885962 0.611588 0.158069 11.00000 0.01702 0.01671 = 0.01903 0.00335 0.00676 0.00287 REM AFIX 13 H35 2 0.965988 0.626122 0.134566 11.00000 0.02362 REM AFIX 0 C36 1 0.697836 0.446558 0.075208 11.00000 0.02436 0.01964 = 0.01805 0.00260 0.00717 0.00622 REM AFIX 43 H36 2 0.685681 0.515175 0.049715 11.00000 0.02736 REM AFIX 0 C37 1 0.614474 0.323487 0.053006 11.00000 0.02536 0.02256 = 0.01835 -0.00170 0.00324 0.00498 REM AFIX 43 H37 2 0.544185 0.305940 0.011934 11.00000 0.03406 REM AFIX 0 C38 1 0.631218 0.226252 0.089707 11.00000 0.02478 0.01758 = 0.02348 -0.00226 0.00599 0.00166 REM AFIX 43 H38 2 0.571239 0.139793 0.074361 11.00000 0.02810 REM AFIX 0 C39 1 0.731531 0.252867 0.147893 11.00000 0.02147 0.01601 = 0.02174 0.00193 0.00726 0.00401 REM AFIX 43 H39 2 0.742551 0.185598 0.174044 11.00000 0.02209 REM AFIX 0 C40 1 1.124428 0.581192 0.307884 11.00000 0.01479 0.01623 = 0.02049 0.00261 0.00586 0.00031 C41 1 1.252318 0.534768 0.328860 11.00000 0.01747 0.02143 = 0.02413 -0.00053 0.00596 0.00487 REM AFIX 43 H41 2 1.278093 0.468241 0.300186 11.00000 0.02911 REM AFIX 0 C42 1 1.341079 0.581013 0.388857 11.00000 0.01784 0.02642 = 0.02482 0.00195 0.00417 0.00677 REM AFIX 43 H42 2 1.432825 0.551647 0.403644 11.00000 0.03369 REM AFIX 0 C43 1 1.305181 0.677250 0.428603 11.00000 0.01959 0.02169 = 0.01831 0.00270 0.00559 0.00024 O43 3 1.405807 0.723363 0.485052 11.00000 0.02536 0.03034 = 0.01976 -0.00185 0.00207 0.00483 C44 1 1.175555 0.721327 0.409342 11.00000 0.02216 0.02002 = 0.02174 0.00149 0.00958 0.00402 REM AFIX 43 H44 2 1.147902 0.788276 0.437038 11.00000 0.02627 REM AFIX 0 C45 1 1.086017 0.672238 0.349331 11.00000 0.01717 0.01978 = 0.02332 0.00335 0.00742 0.00447 REM AFIX 43 H45 2 0.997918 0.703709 0.335079 11.00000 0.02716 REM AFIX 0 C46 1 1.389845 0.840468 0.520138 11.00000 0.03098 0.02731 = 0.02492 -0.00425 0.00616 -0.00067 REM AFIX 137 H46A 2 1.383191 0.910060 0.492849 11.00000 0.03734 H46B 2 1.476301 0.863241 0.555336 11.00000 0.03755 H46C 2 1.299831 0.827880 0.536804 11.00000 0.03403 REM AFIX 0 C47 1 0.844286 0.400883 0.289439 11.00000 0.01582 0.01279 = 0.01933 0.00161 0.00435 0.00101 C48 1 0.908497 0.362953 0.346108 11.00000 0.01638 0.01927 = 0.02422 0.00585 0.00242 0.00186 REM AFIX 43 H48 2 1.000996 0.336420 0.350596 11.00000 0.02887 REM AFIX 0 C49 1 0.839773 0.364027 0.396354 11.00000 0.02628 0.02463 = 0.02018 0.00616 0.00288 0.00051 REM AFIX 43 H49 2 0.887342 0.335894 0.435498 11.00000 0.03224 REM AFIX 0 C50 1 0.704575 0.401311 0.390571 11.00000 0.03022 0.02538 = 0.02252 0.00230 0.01216 0.00301 REM AFIX 43 H50 2 0.655246 0.400631 0.425398 11.00000 0.03177 REM AFIX 0 C51 1 0.639630 0.438175 0.334406 11.00000 0.02285 0.02734 = 0.02660 0.00337 0.01053 0.00871 REM AFIX 43 H51 2 0.543779 0.463747 0.328798 11.00000 0.03457 REM AFIX 0 C52 1 0.709119 0.438524 0.284324 11.00000 0.01921 0.02002 = 0.02054 0.00390 0.00544 0.00618 REM AFIX 43 H52 2 0.661554 0.464501 0.244483 11.00000 0.02167 REM AFIX 0 C53 1 0.791476 0.712223 0.148164 11.00000 0.01685 0.01312 = 0.02099 0.00157 0.00396 0.00087 C54 1 0.704059 0.737614 0.190393 11.00000 0.02170 0.01540 = 0.02199 0.00224 0.00643 0.00274 REM AFIX 43 H54 2 0.710573 0.693952 0.228054 11.00000 0.01917 REM AFIX 0 C55 1 0.609378 0.823490 0.179912 11.00000 0.02327 0.01781 = 0.02927 0.00065 0.00882 0.00489 REM AFIX 43 H55 2 0.548700 0.840559 0.209576 11.00000 0.02909 REM AFIX 0 C56 1 0.601586 0.885508 0.127185 11.00000 0.02267 0.01638 = 0.03644 0.00559 0.00445 0.00511 REM AFIX 43 H56 2 0.533846 0.945236 0.119111 11.00000 0.03140 REM AFIX 0 C57 1 0.690136 0.862607 0.085593 11.00000 0.02736 0.02164 = 0.02992 0.01133 0.00525 0.00410 REM AFIX 43 H57 2 0.685972 0.906324 0.048938 11.00000 0.03194 REM AFIX 0 C58 1 0.785679 0.776663 0.096161 11.00000 0.02350 0.02108 = 0.02485 0.00670 0.00879 0.00358 REM AFIX 43 H58 2 0.848605 0.761443 0.067182 11.00000 0.02712 REM AFIX 0 HKLF 4 REM JF2849Fmi in P-1 FINAL ALL DATA MERGE-I 17MAY2019 REM wR2 = 0.0959, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0361 for 8901 Fo > 4sig(Fo) and 0.0389 for all 9689 data REM 733 parameters refined using 0 restraints END WGHT 0.0487 0.7055 REM Instructions for potential hydrogen bonds HTAB C12 O13_$1 HTAB C32 O1_$2 REM Highest difference peak 0.377, deepest hole -0.199, 1-sigma level 0.038 Q1 1 0.8835 0.9251 0.7182 11.00000 0.05 0.38 Q2 1 0.8581 0.8939 0.8599 11.00000 0.05 0.37 Q3 1 0.8371 0.5414 0.1483 11.00000 0.05 0.34 Q4 1 1.0773 0.5550 0.2773 11.00000 0.05 0.34 Q5 1 0.8133 1.0507 0.8094 11.00000 0.05 0.33 Q6 1 0.9717 0.4688 0.2400 11.00000 0.05 0.32 Q7 1 0.8487 0.7717 0.8547 11.00000 0.05 0.32 Q8 1 0.8814 0.4041 0.2608 11.00000 0.05 0.31 Q9 1 0.7326 1.0323 0.7546 11.00000 0.05 0.30 Q10 1 0.8314 0.6610 0.1528 11.00000 0.05 0.29 Q11 1 0.7361 0.4653 0.1081 11.00000 0.05 0.29 Q12 1 0.8700 0.3897 0.2017 11.00000 0.05 0.29 Q13 1 1.1037 0.6177 0.3298 11.00000 0.05 0.29 Q14 1 0.8506 0.9947 0.7621 11.00000 0.05 0.29 Q15 1 0.7796 0.7357 0.1217 11.00000 0.05 0.28 Q16 1 0.8544 0.9703 0.9112 11.00000 0.05 0.27 Q17 1 0.8539 0.6907 0.8924 11.00000 0.05 0.27 Q18 1 0.8814 0.3952 0.3213 11.00000 0.05 0.27 Q19 1 0.8184 0.4233 0.1507 11.00000 0.05 0.27 Q20 1 0.8286 0.8586 0.6647 11.00000 0.05 0.27 ; _shelx_res_checksum 65181 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_JF2822FMI _database_code_depnum_ccdc_archive 'CCDC 1921673' loop_ _audit_author_name _audit_author_address 'James Fettinger' ;University of California, Davis United States of America ; _audit_update_record ; 2019-06-28 deposited with the CCDC. 2019-11-11 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 O' _chemical_formula_sum 'C23 H20 O' _chemical_formula_weight 312.39 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' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'I 2' _space_group_name_Hall 'I 2y' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 17.3724(8) _cell_length_b 5.5677(3) _cell_length_c 18.8919(12) _cell_angle_alpha 90 _cell_angle_beta 111.6606(19) _cell_angle_gamma 90 _cell_volume 1698.27(16) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 6581 _cell_measurement_theta_min 4.35 _cell_measurement_theta_max 69.29 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_F_000 664 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.167 _exptl_crystal_size_min 0.062 _exptl_absorpt_coefficient_mu 0.562 _shelx_estimated_absorpt_T_min 0.877 _shelx_estimated_absorpt_T_max 0.966 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8379 _exptl_absorpt_correction_T_max 0.9369 _exptl_absorpt_process_details 'SADABS 2016/2 (Sheldrick, 2016)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4368 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.956 _diffrn_reflns_theta_max 69.279 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.944 _diffrn_reflns_point_group_measured_fraction_full 0.961 _reflns_number_total 2996 _reflns_number_gt 2931 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.738 _reflns_Friedel_fraction_max 0.902 _reflns_Friedel_fraction_full 0.924 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Apex2 (2014.9-1) (Bruker, 2014)' _computing_cell_refinement 'SAINT (8.38a) (Bruker, 2017)' _computing_data_reduction 'SAINT (8.38a) (Bruker, 2017)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.4204P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.05(15) _chemical_absolute_configuration ad _refine_ls_number_reflns 2996 _refine_ls_number_parameters 297 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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_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 C1 C 0.88223(11) 0.5106(3) 0.54787(10) 0.0255(4) Uani 1 1 d . . . . . H1 H 0.9380(13) 0.437(4) 0.5713(11) 0.021(5) Uiso 1 1 d . . . . . O1 O 0.88625(7) 0.7507(3) 0.57540(7) 0.0261(3) Uani 1 1 d . . . . . C2 C 0.92784(11) 0.7543(4) 0.65604(10) 0.0261(4) Uani 1 1 d . . . . . H2A H 0.9866(14) 0.712(4) 0.6680(11) 0.024(5) Uiso 1 1 d . . . . . H2B H 0.9244(13) 0.926(5) 0.6719(12) 0.025(5) Uiso 1 1 d . . . . . C3 C 0.89045(10) 0.5850(3) 0.69635(10) 0.0234(4) Uani 1 1 d . . . . . C4 C 0.90622(11) 0.6145(4) 0.77376(11) 0.0276(4) Uani 1 1 d . . . . . H4 H 0.9379(15) 0.757(5) 0.7984(13) 0.036(6) Uiso 1 1 d . . . . . C5 C 0.87671(12) 0.4529(4) 0.81303(10) 0.0304(4) Uani 1 1 d . . . . . H5 H 0.8886(13) 0.471(4) 0.8681(12) 0.027(5) Uiso 1 1 d . . . . . C6 C 0.82925(12) 0.2573(4) 0.77471(10) 0.0291(4) Uani 1 1 d . . . . . H6 H 0.8071(13) 0.147(4) 0.8011(12) 0.022(5) Uiso 1 1 d . . . . . C7 C 0.81161(11) 0.2306(4) 0.69734(10) 0.0259(4) Uani 1 1 d . . . . . H7 H 0.7764(14) 0.089(4) 0.6699(12) 0.028(5) Uiso 1 1 d . . . . . C8 C 0.84211(10) 0.3916(3) 0.65750(10) 0.0228(4) Uani 1 1 d . . . . . C9 C 0.82173(11) 0.3586(3) 0.57255(10) 0.0234(4) Uani 1 1 d . . . . . H9 H 0.8334(12) 0.188(4) 0.5630(11) 0.016(5) Uiso 1 1 d . . . . . C10 C 0.86022(11) 0.5221(4) 0.46330(10) 0.0275(4) Uani 1 1 d . . . . . H10 H 0.8238(15) 0.651(5) 0.4373(14) 0.039(6) Uiso 1 1 d . . . . . C11 C 0.88890(11) 0.3643(4) 0.42653(10) 0.0267(4) Uani 1 1 d . . . . . H11 H 0.9263(15) 0.233(5) 0.4574(13) 0.037(6) Uiso 1 1 d . . . . . C12 C 0.87463(10) 0.3555(3) 0.34463(10) 0.0250(4) Uani 1 1 d . . . . . C13 C 0.90741(12) 0.1629(4) 0.31792(11) 0.0292(4) Uani 1 1 d . . . . . H13 H 0.9385(14) 0.037(5) 0.3536(13) 0.029(6) Uiso 1 1 d . . . . . C14 C 0.89810(12) 0.1463(4) 0.24194(10) 0.0293(4) Uani 1 1 d . . . . . H14 H 0.9216(15) 0.007(5) 0.2249(13) 0.035(6) Uiso 1 1 d . . . . . C15 C 0.85606(11) 0.3248(4) 0.19110(10) 0.0283(4) Uani 1 1 d . . . . . H15 H 0.8507(13) 0.312(4) 0.1394(13) 0.028(6) Uiso 1 1 d . . . . . C16 C 0.82332(11) 0.5179(4) 0.21700(11) 0.0286(4) Uani 1 1 d . . . . . H16 H 0.7918(14) 0.646(5) 0.1808(13) 0.031(6) Uiso 1 1 d . . . . . C17 C 0.83217(11) 0.5329(4) 0.29272(11) 0.0272(4) Uani 1 1 d . . . . . H17 H 0.8113(14) 0.658(5) 0.3089(13) 0.029(6) Uiso 1 1 d . . . . . C18 C 0.73120(11) 0.4108(3) 0.52672(9) 0.0227(4) Uani 1 1 d . . . . . C19 C 0.68483(11) 0.2462(4) 0.47256(10) 0.0275(4) Uani 1 1 d . . . . . H19 H 0.7108(13) 0.098(4) 0.4659(12) 0.026(5) Uiso 1 1 d . . . . . C20 C 0.60115(12) 0.2858(4) 0.43019(11) 0.0302(4) Uani 1 1 d . . . . . H20 H 0.5703(15) 0.167(5) 0.3949(14) 0.038(6) Uiso 1 1 d . . . . . C21 C 0.56319(11) 0.4930(4) 0.44119(10) 0.0282(4) Uani 1 1 d . . . . . H21 H 0.5025(15) 0.524(4) 0.4107(13) 0.032(6) Uiso 1 1 d . . . . . C22 C 0.60912(11) 0.6609(4) 0.49455(10) 0.0270(4) Uani 1 1 d . . . . . H22 H 0.5856(13) 0.803(4) 0.5035(12) 0.024(5) Uiso 1 1 d . . . . . C23 C 0.69226(11) 0.6195(4) 0.53706(10) 0.0249(4) Uani 1 1 d . . . . . H23 H 0.7245(14) 0.737(5) 0.5746(13) 0.035(6) 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 C1 0.0222(8) 0.0286(10) 0.0263(9) 0.0012(8) 0.0096(7) 0.0031(8) O1 0.0254(6) 0.0276(7) 0.0250(6) 0.0010(5) 0.0090(5) -0.0010(5) C2 0.0208(9) 0.0290(10) 0.0264(9) -0.0013(8) 0.0062(7) -0.0014(8) C3 0.0177(7) 0.0254(9) 0.0245(8) 0.0004(7) 0.0049(6) 0.0033(7) C4 0.0226(8) 0.0301(10) 0.0254(9) -0.0025(8) 0.0033(7) 0.0008(8) C5 0.0290(9) 0.0387(11) 0.0214(8) 0.0004(8) 0.0070(7) 0.0050(8) C6 0.0296(9) 0.0311(10) 0.0282(9) 0.0058(9) 0.0124(7) 0.0042(9) C7 0.0242(8) 0.0259(9) 0.0270(9) 0.0003(8) 0.0090(7) -0.0003(8) C8 0.0194(8) 0.0244(9) 0.0233(8) 0.0005(7) 0.0063(6) 0.0035(7) C9 0.0222(8) 0.0248(9) 0.0231(8) -0.0021(7) 0.0082(7) 0.0010(7) C10 0.0237(8) 0.0326(10) 0.0277(9) 0.0016(8) 0.0114(7) 0.0008(8) C11 0.0222(8) 0.0309(10) 0.0264(9) 0.0005(8) 0.0081(7) 0.0007(8) C12 0.0190(8) 0.0298(10) 0.0266(9) -0.0017(8) 0.0087(7) -0.0030(8) C13 0.0282(9) 0.0316(10) 0.0271(9) 0.0027(8) 0.0094(7) 0.0053(8) C14 0.0299(9) 0.0315(10) 0.0280(9) -0.0021(8) 0.0122(7) 0.0040(8) C15 0.0270(9) 0.0351(10) 0.0240(9) 0.0006(8) 0.0109(7) -0.0011(8) C16 0.0259(8) 0.0304(10) 0.0298(9) 0.0055(8) 0.0106(7) 0.0018(8) C17 0.0246(8) 0.0270(9) 0.0326(10) -0.0022(8) 0.0137(7) 0.0003(8) C18 0.0227(8) 0.0272(9) 0.0194(8) 0.0006(7) 0.0091(6) -0.0019(7) C19 0.0265(9) 0.0287(9) 0.0258(8) -0.0033(8) 0.0081(7) 0.0008(8) C20 0.0271(9) 0.0336(11) 0.0265(9) -0.0070(8) 0.0058(8) -0.0032(8) C21 0.0231(8) 0.0372(11) 0.0230(8) 0.0002(8) 0.0071(7) 0.0002(8) C22 0.0265(9) 0.0315(10) 0.0244(8) -0.0029(7) 0.0109(7) 0.0038(8) C23 0.0247(8) 0.0281(9) 0.0214(8) -0.0043(7) 0.0081(7) -0.0015(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 C1 O1 1.427(2) . ? C1 C10 1.501(2) . ? C1 C9 1.549(2) . ? C1 H1 0.99(2) . ? O1 C2 1.425(2) . ? C2 C3 1.502(3) . ? C2 H2A 0.99(2) . ? C2 H2B 1.01(3) . ? C3 C4 1.395(3) . ? C3 C8 1.396(2) . ? C4 C5 1.380(3) . ? C4 H4 0.98(3) . ? C5 C6 1.396(3) . ? C5 H5 0.99(2) . ? C6 C7 1.386(2) . ? C6 H6 0.96(2) . ? C7 C8 1.395(3) . ? C7 H7 1.01(2) . ? C8 C9 1.522(2) . ? C9 C18 1.517(2) . ? C9 H9 1.00(2) . ? C10 C11 1.326(3) . ? C10 H10 0.96(3) . ? C11 C12 1.475(2) . ? C11 H11 1.01(3) . ? C12 C13 1.393(3) . ? C12 C17 1.395(3) . ? C13 C14 1.387(3) . ? C13 H13 0.99(2) . ? C14 C15 1.388(3) . ? C14 H14 0.98(3) . ? C15 C16 1.387(3) . ? C15 H15 0.95(2) . ? C16 C17 1.384(3) . ? C16 H16 1.00(2) . ? C17 H17 0.89(3) . ? C18 C19 1.388(3) . ? C18 C23 1.394(3) . ? C19 C20 1.394(3) . ? C19 H19 0.97(2) . ? C20 C21 1.382(3) . ? C20 H20 0.95(3) . ? C21 C22 1.390(3) . ? C21 H21 1.01(2) . ? C22 C23 1.389(3) . ? C22 H22 0.93(2) . ? C23 H23 0.98(3) . ? 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 O1 C1 C10 107.87(15) . . ? O1 C1 C9 110.45(14) . . ? C10 C1 C9 114.17(15) . . ? O1 C1 H1 108.4(13) . . ? C10 C1 H1 108.4(12) . . ? C9 C1 H1 107.4(12) . . ? C2 O1 C1 109.87(14) . . ? O1 C2 C3 112.95(15) . . ? O1 C2 H2A 108.3(12) . . ? C3 C2 H2A 109.8(13) . . ? O1 C2 H2B 105.6(12) . . ? C3 C2 H2B 111.1(13) . . ? H2A C2 H2B 109.1(18) . . ? C4 C3 C8 119.32(17) . . ? C4 C3 C2 120.22(16) . . ? C8 C3 C2 120.42(16) . . ? C5 C4 C3 121.24(18) . . ? C5 C4 H4 121.9(14) . . ? C3 C4 H4 116.9(15) . . ? C4 C5 C6 119.69(17) . . ? C4 C5 H5 121.6(14) . . ? C6 C5 H5 118.7(14) . . ? C7 C6 C5 119.28(18) . . ? C7 C6 H6 120.4(13) . . ? C5 C6 H6 120.2(13) . . ? C6 C7 C8 121.32(18) . . ? C6 C7 H7 118.6(13) . . ? C8 C7 H7 120.1(13) . . ? C7 C8 C3 119.13(16) . . ? C7 C8 C9 120.33(16) . . ? C3 C8 C9 120.54(16) . . ? C18 C9 C8 111.56(14) . . ? C18 C9 C1 113.53(15) . . ? C8 C9 C1 109.40(14) . . ? C18 C9 H9 108.4(11) . . ? C8 C9 H9 108.7(11) . . ? C1 C9 H9 104.9(11) . . ? C11 C10 C1 122.15(17) . . ? C11 C10 H10 122.0(15) . . ? C1 C10 H10 115.8(15) . . ? C10 C11 C12 128.43(17) . . ? C10 C11 H11 117.7(14) . . ? C12 C11 H11 113.9(14) . . ? C13 C12 C17 118.09(16) . . ? C13 C12 C11 118.21(17) . . ? C17 C12 C11 123.67(17) . . ? C14 C13 C12 121.26(18) . . ? C14 C13 H13 119.0(14) . . ? C12 C13 H13 119.7(14) . . ? C13 C14 C15 119.95(18) . . ? C13 C14 H14 119.1(13) . . ? C15 C14 H14 120.9(13) . . ? C16 C15 C14 119.37(17) . . ? C16 C15 H15 121.5(14) . . ? C14 C15 H15 119.1(14) . . ? C17 C16 C15 120.51(18) . . ? C17 C16 H16 119.2(14) . . ? C15 C16 H16 120.2(14) . . ? C16 C17 C12 120.81(18) . . ? C16 C17 H17 119.9(15) . . ? C12 C17 H17 119.3(15) . . ? C19 C18 C23 118.28(16) . . ? C19 C18 C9 119.44(17) . . ? C23 C18 C9 122.27(16) . . ? C18 C19 C20 121.14(19) . . ? C18 C19 H19 119.1(12) . . ? C20 C19 H19 119.7(12) . . ? C21 C20 C19 120.00(18) . . ? C21 C20 H20 120.5(15) . . ? C19 C20 H20 119.5(15) . . ? C20 C21 C22 119.49(17) . . ? C20 C21 H21 120.6(14) . . ? C22 C21 H21 119.9(14) . . ? C23 C22 C21 120.25(18) . . ? C23 C22 H22 117.9(13) . . ? C21 C22 H22 121.9(13) . . ? C22 C23 C18 120.82(17) . . ? C22 C23 H23 120.3(14) . . ? C18 C23 H23 118.9(14) . . ? 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 C10 C1 O1 C2 -164.53(13) . . . . ? C9 C1 O1 C2 70.07(18) . . . . ? C1 O1 C2 C3 -54.09(19) . . . . ? O1 C2 C3 C4 -160.97(16) . . . . ? O1 C2 C3 C8 21.4(2) . . . . ? C8 C3 C4 C5 1.7(3) . . . . ? C2 C3 C4 C5 -176.03(17) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 -0.9(3) . . . . ? C5 C6 C7 C8 1.7(3) . . . . ? C6 C7 C8 C3 -0.8(3) . . . . ? C6 C7 C8 C9 -179.87(16) . . . . ? C4 C3 C8 C7 -0.8(2) . . . . ? C2 C3 C8 C7 176.85(16) . . . . ? C4 C3 C8 C9 178.21(16) . . . . ? C2 C3 C8 C9 -4.1(2) . . . . ? C7 C8 C9 C18 70.0(2) . . . . ? C3 C8 C9 C18 -109.04(18) . . . . ? C7 C8 C9 C1 -163.56(16) . . . . ? C3 C8 C9 C1 17.4(2) . . . . ? O1 C1 C9 C18 75.86(19) . . . . ? C10 C1 C9 C18 -45.9(2) . . . . ? O1 C1 C9 C8 -49.47(18) . . . . ? C10 C1 C9 C8 -171.22(15) . . . . ? O1 C1 C10 C11 146.39(18) . . . . ? C9 C1 C10 C11 -90.4(2) . . . . ? C1 C10 C11 C12 -178.39(17) . . . . ? C10 C11 C12 C13 -176.18(19) . . . . ? C10 C11 C12 C17 5.7(3) . . . . ? C17 C12 C13 C14 -0.2(3) . . . . ? C11 C12 C13 C14 -178.39(17) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C12 0.5(3) . . . . ? C13 C12 C17 C16 -0.3(3) . . . . ? C11 C12 C17 C16 177.78(17) . . . . ? C8 C9 C18 C19 -130.14(17) . . . . ? C1 C9 C18 C19 105.7(2) . . . . ? C8 C9 C18 C23 49.7(2) . . . . ? C1 C9 C18 C23 -74.5(2) . . . . ? C23 C18 C19 C20 -0.9(3) . . . . ? C9 C18 C19 C20 178.94(17) . . . . ? C18 C19 C20 C21 0.7(3) . . . . ? C19 C20 C21 C22 0.1(3) . . . . ? C20 C21 C22 C23 -0.7(3) . . . . ? C21 C22 C23 C18 0.5(3) . . . . ? C19 C18 C23 C22 0.3(3) . . . . ? C9 C18 C23 C22 -179.52(17) . . . . ? 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 _geom_hbond_publ_flag C9 H9 O1 1.00(2) 2.58(2) 3.560(2) 165.3(15) 1_545 yes _refine_diff_density_max 0.372 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.031 _shelx_res_file ; TITL JF2822Fmi in I2 FINAL ALL DATA MERGE-I 26FEB2019 JF2822FMI.res created by SHELXL-2018/3 at 14:48:47 on 12-Mar-2019 CELL 1.54178 17.3724 5.5677 18.8919 90.0000 111.6606 90.0000 ZERR 4.00 0.0008 0.0003 0.0012 0.0000 0.0019 0.0000 LATT -2 SYMM -X, Y, -Z SFAC C H O UNIT 92 80 4 OMIT 1 1 0 L.S. 9 ACTA BOND $H FMAP 2 PLAN 20 HTAB REM BIND H11 H31 WPDB -2 CONF SIZE 0.062 0.167 0.240 EQIV $1 x, y-1, z HTAB C9 O1_$1 TEMP -183. WGHT 0.050900 0.420400 FVAR 0.12805 C1 1 0.882226 0.510561 0.547871 11.00000 0.02219 0.02859 = 0.02626 0.00121 0.00965 0.00309 H1 2 0.938020 0.436825 0.571312 11.00000 0.02111 O1 3 0.886250 0.750714 0.575399 11.00000 0.02539 0.02762 = 0.02499 0.00096 0.00898 -0.00103 C2 1 0.927836 0.754255 0.656040 11.00000 0.02079 0.02899 = 0.02641 -0.00128 0.00619 -0.00135 H2A 2 0.986626 0.711987 0.667959 11.00000 0.02416 H2B 2 0.924386 0.926293 0.671937 11.00000 0.02517 C3 1 0.890451 0.584964 0.696355 11.00000 0.01770 0.02543 = 0.02447 0.00043 0.00490 0.00334 C4 1 0.906224 0.614540 0.773759 11.00000 0.02256 0.03006 = 0.02538 -0.00247 0.00330 0.00085 H4 2 0.937937 0.756599 0.798371 11.00000 0.03558 C5 1 0.876709 0.452934 0.813035 11.00000 0.02895 0.03873 = 0.02143 0.00044 0.00696 0.00497 H5 2 0.888650 0.471192 0.868059 11.00000 0.02746 C6 1 0.829252 0.257322 0.774710 11.00000 0.02957 0.03110 = 0.02824 0.00584 0.01243 0.00421 H6 2 0.807084 0.147260 0.801140 11.00000 0.02218 C7 1 0.811609 0.230566 0.697343 11.00000 0.02423 0.02593 = 0.02702 0.00028 0.00898 -0.00027 H7 2 0.776401 0.089009 0.669938 11.00000 0.02750 C8 1 0.842110 0.391551 0.657504 11.00000 0.01937 0.02437 = 0.02329 0.00054 0.00627 0.00349 C9 1 0.821727 0.358631 0.572547 11.00000 0.02219 0.02476 = 0.02310 -0.00211 0.00818 0.00100 H9 2 0.833442 0.188434 0.563033 11.00000 0.01551 C10 1 0.860225 0.522113 0.463298 11.00000 0.02371 0.03260 = 0.02772 0.00164 0.01135 0.00083 H10 2 0.823770 0.651110 0.437329 11.00000 0.03911 C11 1 0.888901 0.364348 0.426533 11.00000 0.02223 0.03088 = 0.02642 0.00050 0.00813 0.00074 H11 2 0.926275 0.232673 0.457381 11.00000 0.03675 C12 1 0.874634 0.355530 0.344632 11.00000 0.01901 0.02978 = 0.02656 -0.00168 0.00866 -0.00298 C13 1 0.907410 0.162895 0.317924 11.00000 0.02821 0.03163 = 0.02708 0.00270 0.00943 0.00526 H13 2 0.938515 0.036605 0.353612 11.00000 0.02901 C14 1 0.898104 0.146337 0.241939 11.00000 0.02987 0.03149 = 0.02799 -0.00210 0.01219 0.00398 H14 2 0.921576 0.006993 0.224917 11.00000 0.03457 C15 1 0.856062 0.324809 0.191095 11.00000 0.02700 0.03510 = 0.02404 0.00056 0.01087 -0.00108 H15 2 0.850731 0.312369 0.139381 11.00000 0.02838 C16 1 0.823316 0.517941 0.216998 11.00000 0.02588 0.03043 = 0.02985 0.00545 0.01065 0.00181 H16 2 0.791776 0.645748 0.180797 11.00000 0.03145 C17 1 0.832169 0.532903 0.292716 11.00000 0.02465 0.02704 = 0.03258 -0.00225 0.01366 0.00028 H17 2 0.811336 0.657896 0.308860 11.00000 0.02868 C18 1 0.731204 0.410781 0.526716 11.00000 0.02274 0.02724 = 0.01939 0.00065 0.00913 -0.00195 C19 1 0.684833 0.246207 0.472558 11.00000 0.02650 0.02874 = 0.02584 -0.00330 0.00808 0.00077 H19 2 0.710766 0.098251 0.465856 11.00000 0.02593 C20 1 0.601147 0.285829 0.430189 11.00000 0.02713 0.03358 = 0.02653 -0.00701 0.00584 -0.00321 H20 2 0.570252 0.167371 0.394899 11.00000 0.03774 C21 1 0.563191 0.493001 0.441191 11.00000 0.02308 0.03722 = 0.02300 0.00019 0.00708 0.00022 H21 2 0.502475 0.523556 0.410688 11.00000 0.03225 C22 1 0.609118 0.660875 0.494549 11.00000 0.02652 0.03147 = 0.02436 -0.00294 0.01091 0.00384 H22 2 0.585557 0.803036 0.503473 11.00000 0.02445 C23 1 0.692259 0.619459 0.537063 11.00000 0.02471 0.02811 = 0.02144 -0.00428 0.00807 -0.00146 H23 2 0.724527 0.737144 0.574611 11.00000 0.03485 REM H31 2 1.000000 -0.085172 0.500000 10.50000 0.08088 HKLF 4 REM JF2822Fmi in I2 FINAL ALL DATA MERGE-I 26FEB2019 REM wR2 = 0.0800, GooF = S = 1.040, Restrained GooF = 1.040 for all data REM R1 = 0.0301 for 2931 Fo > 4sig(Fo) and 0.0308 for all 2996 data REM 297 parameters refined using 1 restraints END WGHT 0.0527 0.4249 REM Instructions for potential hydrogen bonds HTAB C9 O1_$1 REM Highest difference peak 0.372, deepest hole -0.151, 1-sigma level 0.031 Q1 1 1.0000 -0.0856 0.5000 10.50000 0.05 0.37 Q2 1 0.8572 0.3506 0.4502 11.00000 0.05 0.15 Q3 1 0.9007 0.5103 0.4455 11.00000 0.05 0.15 Q4 1 0.8545 0.4107 0.5604 11.00000 0.05 0.13 Q5 1 0.7022 0.4580 0.5496 11.00000 0.05 0.13 Q6 1 0.8481 0.5392 0.6693 11.00000 0.05 0.12 Q7 1 0.8522 0.2409 0.6839 11.00000 0.05 0.12 Q8 1 1.0000 0.5917 0.5000 10.50000 0.05 0.12 Q9 1 0.7377 0.6138 0.5157 11.00000 0.05 0.12 Q10 1 0.8547 0.4902 0.5036 11.00000 0.05 0.12 Q11 1 0.8003 0.3955 0.6750 11.00000 0.05 0.11 Q12 1 0.9206 0.4679 0.7960 11.00000 0.05 0.11 Q13 1 0.5655 0.3240 0.4475 11.00000 0.05 0.11 Q14 1 0.8626 0.1957 0.3285 11.00000 0.05 0.11 Q15 1 0.5994 0.4505 0.4171 11.00000 0.05 0.11 Q16 1 0.9238 0.6221 0.6778 11.00000 0.05 0.11 Q17 1 0.8640 0.6032 0.7907 11.00000 0.05 0.11 Q18 1 0.9148 0.3245 0.3323 11.00000 0.05 0.11 Q19 1 0.8626 0.5615 0.2668 11.00000 0.05 0.11 Q20 1 0.8373 0.3721 0.6192 11.00000 0.05 0.11 ; _shelx_res_checksum 96318 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_JF2851CuFMI _database_code_depnum_ccdc_archive 'CCDC 1920825' loop_ _audit_author_name _audit_author_address 'James Fettinger' ;University of California, Davis United States of America ; _audit_update_record ; 2019-06-04 deposited with the CCDC. 2019-11-11 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O2' _chemical_formula_sum 'C18 H17 N O2' _chemical_formula_weight 279.32 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' N N 0.0311 0.0180 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.0262(4) _cell_length_b 10.7097(4) _cell_length_c 14.6781(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1418.90(10) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9967 _cell_measurement_theta_min 5.11 _cell_measurement_theta_max 72.15 _exptl_crystal_description Rod _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_F_000 592 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.764 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.115 _exptl_absorpt_coefficient_mu 0.679 _shelx_estimated_absorpt_T_min 0.625 _shelx_estimated_absorpt_T_max 0.926 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7268 _exptl_absorpt_correction_T_max 0.8416 _exptl_absorpt_process_details 'SADABS 2016/2 (Sheldrick, 2016)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7991 _diffrn_reflns_av_unetI/netI 0.0174 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.112 _diffrn_reflns_theta_max 72.141 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 2743 _reflns_number_gt 2718 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.720 _reflns_Friedel_fraction_max 0.982 _reflns_Friedel_fraction_full 0.999 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Apex2 (2014.9-1) (Bruker, 2014)' _computing_cell_refinement 'SAINT (8.38a) (Bruker, 2017)' _computing_data_reduction 'SAINT (8.38a) (Bruker, 2017)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; JF2851 Duo Cu A colorless rod with approximate orthogonal dimensions 0.764 x 0.170 x 0.115mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD system at --183\%C(90K). Indexing of the unit cell used a random set of reflections collected from three series of 0.5\% wide omega-scans, 10 seconds per frame, and 30 frames per series that were well distributed in reciprocal space. Data were collected [CuKa] with 0.5\% wide scans, variable time per frame dependent upon detector 2theta angle and varying phi and omega angles such that nearly all unique reflections were collected at least once. The crystal to detector distance was 5.15cm, thus providing a complete sphere of data to 2thetamax=144.23\%. Structural determination and Refinement: All crystallographic calculations were performed on an Intel Xeon E5-1620v2 at 3.70GHz an eight core processor and 16GB of extended memory. Data collected were corrected for Lorentz and polarization effects with Saint(1) and absorption using Blessing?s method and merged as incorporated with the program Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the probable space group and set up the initial files. System symmetry, systematic absences and intensity statistics indicated the non- centrosymmetric orthorhombic space group P212121 (no. 19). The structure was determined by direct methods with the non-hydrogen atoms being located directly for the molecule using the program XT(5). The structure was refined with XL(6). The data collected were merged for least squares refinement to 2743 unique data [R(int)=0.0192]. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were idealized initially and then allowed to refine freely throughout the final refinement stages. The final structure was refined to convergence with R(F)=2.63%, wR(F2)=6.97%, GOF=1.065 for all 2743 unique reflections [R(F)=2.62, wR(F2)=6.96% for those 2718 data with Fo > 4sigma(Fo)]. The final difference- Fourier map was featureless indicating that the structure is both correct and complete. An empirical correction for extinction was also attempted and found to be 0.0028(5). The absolute structure parameters were determined to be: Flack(x)(7), 0.03(5); Hooft(y)(8), 0.01(4) and Parsons(z)(6), 0.02(5) indicating that the structure?s absolute configuration has been determined reliably. References: 1. Bruker (2013) APEXII (Version 2014.9-1) and (2016) SAINT (Version 8.37a). Bruker AXS Inc., Madison, Wisconsin, USA. 2. An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38. 3. Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector Absorption Correction? Universit\"at G\"ottingen: G\"ottingen, Germany. 4. Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA. 5. Sheldrick, G. M., (2014) SHELXT, Universit\"at G\"ottingen: G\"ottingen, Germany. Structure determination program. Private communication. 6. Sheldrick, G. M., (2018). SHELXL2018/3. Universit\"at G\"ottingen: G\"ottingen, Germany. 7. On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39, 876-881. 8. Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst. 41, 96- 103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron Acknowledgment: We thank the National Science Foundation (Grant CHE-0840444) for the Dual Source X-ray diffractometer. J.C. Fettinger ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.2099P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_extinction_coef 0.0028(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 2743 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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_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 C1 C 0.43521(17) 0.47948(15) 0.25612(11) 0.0202(3) Uani 1 1 d . . . . . N1 N 0.49138(14) 0.54330(11) 0.32789(9) 0.0178(3) Uani 1 1 d . . . . . O1 O 0.33442(13) 0.40449(11) 0.26328(8) 0.0274(3) Uani 1 1 d . . . . . C2 C 0.59063(18) 0.60580(15) 0.16047(11) 0.0232(3) Uani 1 1 d . . . . . H2A H 0.531(2) 0.6821(18) 0.1619(13) 0.023(5) Uiso 1 1 d . . . . . H2B H 0.638(2) 0.5951(19) 0.1011(14) 0.026(5) Uiso 1 1 d . . . . . O2 O 0.49352(13) 0.49906(10) 0.17238(8) 0.0249(3) Uani 1 1 d . . . . . C3 C 0.70347(18) 0.60774(14) 0.23592(10) 0.0198(3) Uani 1 1 d . . . . . H3A H 0.774(2) 0.6792(19) 0.2276(13) 0.021(5) Uiso 1 1 d . . . . . H3B H 0.761(2) 0.532(2) 0.2342(14) 0.025(5) Uiso 1 1 d . . . . . C4 C 0.62387(16) 0.62327(12) 0.32605(10) 0.0166(3) Uani 1 1 d . . . . . H4 H 0.592(2) 0.7100(18) 0.3317(12) 0.019(4) Uiso 1 1 d . . . . . C5 C 0.72345(16) 0.59466(14) 0.40901(10) 0.0165(3) Uani 1 1 d . . . . . H5 H 0.799(2) 0.6552(17) 0.4078(13) 0.017(4) Uiso 1 1 d . . . . . C6 C 0.63385(17) 0.61228(13) 0.49519(10) 0.0179(3) Uani 1 1 d . . . . . C7 C 0.70081(18) 0.65653(14) 0.57464(11) 0.0214(3) Uani 1 1 d . . . . . H7 H 0.806(2) 0.676(2) 0.5735(14) 0.027(5) Uiso 1 1 d . . . . . C8 C 0.6194(2) 0.67167(14) 0.65389(11) 0.0239(3) Uani 1 1 d . . . . . H8 H 0.670(2) 0.703(2) 0.7090(15) 0.033(5) Uiso 1 1 d . . . . . C9 C 0.46901(19) 0.64136(14) 0.65447(10) 0.0241(3) Uani 1 1 d . . . . . H9 H 0.408(2) 0.6480(18) 0.7108(14) 0.021(4) Uiso 1 1 d . . . . . C10 C 0.40155(17) 0.59961(14) 0.57546(11) 0.0215(3) Uani 1 1 d . . . . . H10 H 0.299(2) 0.5790(18) 0.5772(13) 0.022(5) Uiso 1 1 d . . . . . C11 C 0.48299(18) 0.58474(13) 0.49524(10) 0.0184(3) Uani 1 1 d . . . . . C12 C 0.40480(16) 0.53424(14) 0.41243(11) 0.0201(3) Uani 1 1 d . . . . . H12A H 0.382(2) 0.4474(18) 0.4216(12) 0.017(4) Uiso 1 1 d . . . . . H12B H 0.311(2) 0.5766(18) 0.4046(13) 0.020(4) Uiso 1 1 d . . . . . C13 C 0.79980(16) 0.46817(14) 0.40673(10) 0.0170(3) Uani 1 1 d . . . . . C14 C 0.72271(17) 0.35605(14) 0.41644(10) 0.0185(3) Uani 1 1 d . . . . . H14 H 0.622(2) 0.3563(17) 0.4279(13) 0.024(5) Uiso 1 1 d . . . . . C15 C 0.79609(17) 0.24184(14) 0.41446(11) 0.0204(3) Uani 1 1 d . . . . . H15 H 0.738(2) 0.163(2) 0.4191(14) 0.028(5) Uiso 1 1 d . . . . . C16 C 0.94914(17) 0.23786(15) 0.40385(10) 0.0212(3) Uani 1 1 d . . . . . H16 H 1.001(2) 0.1571(18) 0.4033(13) 0.024(5) Uiso 1 1 d . . . . . C17 C 1.02786(17) 0.34852(16) 0.39551(10) 0.0215(3) Uani 1 1 d . . . . . H17 H 1.134(2) 0.3471(18) 0.3906(13) 0.024(5) Uiso 1 1 d . . . . . C18 C 0.95361(16) 0.46256(15) 0.39653(10) 0.0193(3) Uani 1 1 d . . . . . H18 H 1.007(2) 0.5390(19) 0.3916(12) 0.024(5) 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 C1 0.0184(7) 0.0192(7) 0.0231(7) -0.0022(6) -0.0011(5) 0.0019(6) N1 0.0175(6) 0.0170(6) 0.0190(6) 0.0001(5) 0.0001(5) -0.0012(5) O1 0.0252(6) 0.0255(6) 0.0316(6) -0.0064(5) 0.0004(5) -0.0068(5) C2 0.0282(8) 0.0240(7) 0.0174(7) 0.0014(6) 0.0007(6) -0.0001(7) O2 0.0277(6) 0.0269(6) 0.0200(5) -0.0039(4) -0.0009(4) -0.0042(5) C3 0.0220(7) 0.0187(7) 0.0187(7) 0.0014(6) 0.0031(6) 0.0003(6) C4 0.0174(6) 0.0136(6) 0.0188(7) 0.0006(6) 0.0006(6) -0.0015(5) C5 0.0167(6) 0.0147(6) 0.0182(7) 0.0004(6) 0.0012(6) -0.0033(5) C6 0.0224(7) 0.0120(6) 0.0193(7) 0.0013(5) 0.0020(6) 0.0020(6) C7 0.0249(8) 0.0176(7) 0.0217(7) 0.0006(6) -0.0017(6) 0.0029(6) C8 0.0331(9) 0.0197(7) 0.0189(7) -0.0009(6) -0.0020(6) 0.0053(6) C9 0.0340(9) 0.0190(7) 0.0193(7) 0.0019(6) 0.0060(7) 0.0090(6) C10 0.0231(8) 0.0159(6) 0.0256(8) 0.0033(6) 0.0048(6) 0.0049(6) C11 0.0216(7) 0.0124(6) 0.0212(7) 0.0028(6) 0.0020(6) 0.0030(6) C12 0.0164(7) 0.0205(7) 0.0233(7) -0.0004(6) 0.0036(6) -0.0002(6) C13 0.0184(6) 0.0194(7) 0.0132(6) -0.0002(6) -0.0002(5) -0.0009(6) C14 0.0167(7) 0.0194(7) 0.0193(7) 0.0015(6) 0.0009(5) -0.0005(5) C15 0.0218(7) 0.0188(7) 0.0205(7) 0.0022(6) 0.0003(6) -0.0015(6) C16 0.0228(7) 0.0215(8) 0.0194(7) 0.0019(6) -0.0007(6) 0.0044(6) C17 0.0164(7) 0.0275(8) 0.0205(7) 0.0013(6) -0.0009(6) 0.0027(6) C18 0.0185(7) 0.0213(7) 0.0180(7) -0.0003(6) 0.0008(5) -0.0026(6) _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 C1 O1 1.2180(19) . ? C1 O2 1.3534(19) . ? C1 N1 1.354(2) . ? N1 C12 1.4697(19) . ? N1 C4 1.4712(18) . ? C2 O2 1.4511(19) . ? C2 C3 1.505(2) . ? C2 H2A 0.98(2) . ? C2 H2B 0.98(2) . ? C3 C4 1.515(2) . ? C3 H3A 1.01(2) . ? C3 H3B 0.97(2) . ? C4 C5 1.544(2) . ? C4 H4 0.976(19) . ? C5 C6 1.513(2) . ? C5 C13 1.520(2) . ? C5 H5 0.939(19) . ? C6 C11 1.393(2) . ? C6 C7 1.396(2) . ? C7 C8 1.385(2) . ? C7 H7 0.97(2) . ? C8 C9 1.396(3) . ? C8 H8 0.99(2) . ? C9 C10 1.384(2) . ? C9 H9 1.00(2) . ? C10 C11 1.397(2) . ? C10 H10 0.96(2) . ? C11 C12 1.506(2) . ? C12 H12A 0.962(19) . ? C12 H12B 0.97(2) . ? C13 C14 1.395(2) . ? C13 C18 1.398(2) . ? C14 C15 1.391(2) . ? C14 H14 0.93(2) . ? C15 C16 1.391(2) . ? C15 H15 1.00(2) . ? C16 C17 1.387(2) . ? C16 H16 0.98(2) . ? C17 C18 1.393(2) . ? C17 H17 0.96(2) . ? C18 H18 0.95(2) . ? 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 O1 C1 O2 118.09(14) . . ? O1 C1 N1 123.04(14) . . ? O2 C1 N1 118.86(13) . . ? C1 N1 C12 115.12(12) . . ? C1 N1 C4 125.73(13) . . ? C12 N1 C4 119.08(12) . . ? O2 C2 C3 109.33(12) . . ? O2 C2 H2A 108.9(11) . . ? C3 C2 H2A 110.2(11) . . ? O2 C2 H2B 106.3(12) . . ? C3 C2 H2B 111.1(12) . . ? H2A C2 H2B 111.0(16) . . ? C1 O2 C2 117.80(12) . . ? C2 C3 C4 108.86(13) . . ? C2 C3 H3A 110.7(11) . . ? C4 C3 H3A 108.9(11) . . ? C2 C3 H3B 109.5(12) . . ? C4 C3 H3B 111.7(12) . . ? H3A C3 H3B 107.1(15) . . ? N1 C4 C3 109.73(12) . . ? N1 C4 C5 110.07(11) . . ? C3 C4 C5 113.01(12) . . ? N1 C4 H4 108.4(11) . . ? C3 C4 H4 108.5(11) . . ? C5 C4 H4 107.0(11) . . ? C6 C5 C13 111.83(12) . . ? C6 C5 C4 108.86(12) . . ? C13 C5 C4 115.04(12) . . ? C6 C5 H5 108.4(11) . . ? C13 C5 H5 106.7(11) . . ? C4 C5 H5 105.6(11) . . ? C11 C6 C7 119.64(14) . . ? C11 C6 C5 119.76(13) . . ? C7 C6 C5 120.60(14) . . ? C8 C7 C6 120.76(15) . . ? C8 C7 H7 120.6(12) . . ? C6 C7 H7 118.7(12) . . ? C7 C8 C9 119.58(15) . . ? C7 C8 H8 118.7(13) . . ? C9 C8 H8 121.7(13) . . ? C10 C9 C8 119.86(14) . . ? C10 C9 H9 118.2(11) . . ? C8 C9 H9 121.9(11) . . ? C9 C10 C11 120.77(15) . . ? C9 C10 H10 118.7(12) . . ? C11 C10 H10 120.5(12) . . ? C6 C11 C10 119.37(14) . . ? C6 C11 C12 122.25(13) . . ? C10 C11 C12 118.33(14) . . ? N1 C12 C11 114.12(12) . . ? N1 C12 H12A 107.1(11) . . ? C11 C12 H12A 109.5(11) . . ? N1 C12 H12B 109.5(11) . . ? C11 C12 H12B 109.8(11) . . ? H12A C12 H12B 106.6(16) . . ? C14 C13 C18 118.00(14) . . ? C14 C13 C5 122.59(12) . . ? C18 C13 C5 119.40(14) . . ? C15 C14 C13 121.14(13) . . ? C15 C14 H14 118.3(12) . . ? C13 C14 H14 120.4(12) . . ? C16 C15 C14 120.14(14) . . ? C16 C15 H15 120.3(12) . . ? C14 C15 H15 119.5(12) . . ? C17 C16 C15 119.51(15) . . ? C17 C16 H16 120.3(12) . . ? C15 C16 H16 120.2(12) . . ? C16 C17 C18 120.10(13) . . ? C16 C17 H17 120.3(12) . . ? C18 C17 H17 119.6(12) . . ? C17 C18 C13 121.11(14) . . ? C17 C18 H18 120.6(12) . . ? C13 C18 H18 118.3(12) . . ? 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 N1 C12 -11.1(2) . . . . ? O2 C1 N1 C12 169.20(12) . . . . ? O1 C1 N1 C4 172.15(14) . . . . ? O2 C1 N1 C4 -7.6(2) . . . . ? O1 C1 O2 C2 167.33(14) . . . . ? N1 C1 O2 C2 -12.9(2) . . . . ? C3 C2 O2 C1 48.10(18) . . . . ? O2 C2 C3 C4 -62.50(15) . . . . ? C1 N1 C4 C3 -9.14(19) . . . . ? C12 N1 C4 C3 174.18(12) . . . . ? C1 N1 C4 C5 -134.12(14) . . . . ? C12 N1 C4 C5 49.21(16) . . . . ? C2 C3 C4 N1 42.77(15) . . . . ? C2 C3 C4 C5 166.03(12) . . . . ? N1 C4 C5 C6 -56.69(14) . . . . ? C3 C4 C5 C6 -179.76(12) . . . . ? N1 C4 C5 C13 69.70(15) . . . . ? C3 C4 C5 C13 -53.37(16) . . . . ? C13 C5 C6 C11 -94.97(15) . . . . ? C4 C5 C6 C11 33.25(17) . . . . ? C13 C5 C6 C7 85.36(16) . . . . ? C4 C5 C6 C7 -146.42(13) . . . . ? C11 C6 C7 C8 0.9(2) . . . . ? C5 C6 C7 C8 -179.40(13) . . . . ? C6 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 C10 -1.7(2) . . . . ? C8 C9 C10 C11 1.4(2) . . . . ? C7 C6 C11 C10 -1.2(2) . . . . ? C5 C6 C11 C10 179.10(13) . . . . ? C7 C6 C11 C12 -178.71(14) . . . . ? C5 C6 C11 C12 1.6(2) . . . . ? C9 C10 C11 C6 0.1(2) . . . . ? C9 C10 C11 C12 177.65(13) . . . . ? C1 N1 C12 C11 168.95(12) . . . . ? C4 N1 C12 C11 -14.03(18) . . . . ? C6 C11 C12 N1 -13.0(2) . . . . ? C10 C11 C12 N1 169.48(12) . . . . ? C6 C5 C13 C14 55.33(18) . . . . ? C4 C5 C13 C14 -69.53(18) . . . . ? C6 C5 C13 C18 -123.24(15) . . . . ? C4 C5 C13 C18 111.90(15) . . . . ? C18 C13 C14 C15 -1.1(2) . . . . ? C5 C13 C14 C15 -179.69(14) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? C14 C15 C16 C17 0.2(2) . . . . ? C15 C16 C17 C18 -0.9(2) . . . . ? C16 C17 C18 C13 0.6(2) . . . . ? C14 C13 C18 C17 0.4(2) . . . . ? C5 C13 C18 C17 179.02(13) . . . . ? 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 _geom_hbond_publ_flag C3 H3A O1 1.01(2) 2.61(2) 3.1964(19) 117.2(13) 3_655 yes C4 H4 O1 0.976(19) 2.592(19) 3.3063(18) 130.2(14) 3_655 yes _refine_diff_density_max 0.252 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.034 _shelx_res_file ; TITL JF2851CuFmi in P2(1)2(1)2(1) FINAL ALL DATA MERGE-I 3JUNE2019 JF2851CuFMI.res created by SHELXL-2018/3 at 15:43:07 on 03-Jun-2019 CELL 1.54178 9.0262 10.7097 14.6781 90.0000 90.0000 90.0000 ZERR 4.00 0.0004 0.0004 0.0006 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O UNIT 72 68 4 8 L.S. 9 HTAB EQIV $1 -x+1, y+1/2, -z+1/2 HTAB C3 O1_$1 HTAB C4 O1_$1 WPDB -2 CONF ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.115 0.170 0.764 TEMP -183. WGHT 0.042600 0.209900 EXTI 0.002828 FVAR 0.22751 C1 1 0.435209 0.479480 0.256119 11.00000 0.01835 0.01920 = 0.02309 -0.00225 -0.00114 0.00192 N1 3 0.491375 0.543297 0.327885 11.00000 0.01752 0.01705 = 0.01896 0.00006 0.00008 -0.00124 O1 4 0.334422 0.404489 0.263278 11.00000 0.02520 0.02554 = 0.03159 -0.00640 0.00041 -0.00685 C2 1 0.590629 0.605800 0.160467 11.00000 0.02823 0.02401 = 0.01737 0.00141 0.00074 -0.00007 REM AFIX 23 H2A 2 0.531056 0.682086 0.161879 11.00000 0.02316 H2B 2 0.638181 0.595098 0.101101 11.00000 0.02604 REM AFIX 0 O2 4 0.493516 0.499059 0.172380 11.00000 0.02766 0.02691 = 0.02000 -0.00393 -0.00087 -0.00415 C3 1 0.703468 0.607742 0.235920 11.00000 0.02197 0.01868 = 0.01875 0.00143 0.00308 0.00029 REM AFIX 23 H3A 2 0.774471 0.679240 0.227650 11.00000 0.02127 H3B 2 0.761207 0.531700 0.234228 11.00000 0.02453 REM AFIX 0 C4 1 0.623868 0.623273 0.326050 11.00000 0.01742 0.01364 = 0.01880 0.00060 0.00060 -0.00149 REM AFIX 13 H4 2 0.592266 0.710050 0.331685 11.00000 0.01909 REM AFIX 0 C5 1 0.723452 0.594665 0.409014 11.00000 0.01672 0.01473 = 0.01819 0.00040 0.00121 -0.00326 REM AFIX 13 H5 2 0.798632 0.655189 0.407832 11.00000 0.01687 REM AFIX 0 C6 1 0.633848 0.612284 0.495192 11.00000 0.02240 0.01196 = 0.01933 0.00134 0.00201 0.00196 C7 1 0.700808 0.656529 0.574641 11.00000 0.02486 0.01757 = 0.02174 0.00057 -0.00168 0.00295 REM AFIX 43 H7 2 0.805940 0.675612 0.573480 11.00000 0.02695 REM AFIX 0 C8 1 0.619416 0.671669 0.653890 11.00000 0.03313 0.01969 = 0.01893 -0.00093 -0.00200 0.00528 REM AFIX 43 H8 2 0.670224 0.702831 0.708966 11.00000 0.03309 REM AFIX 0 C9 1 0.469010 0.641360 0.654473 11.00000 0.03396 0.01901 = 0.01925 0.00193 0.00598 0.00902 REM AFIX 43 H9 2 0.407556 0.648011 0.710795 11.00000 0.02052 REM AFIX 0 C10 1 0.401549 0.599607 0.575455 11.00000 0.02311 0.01586 = 0.02564 0.00328 0.00480 0.00489 REM AFIX 43 H10 2 0.298624 0.579030 0.577164 11.00000 0.02227 REM AFIX 0 C11 1 0.482987 0.584741 0.495236 11.00000 0.02161 0.01244 = 0.02116 0.00280 0.00197 0.00300 C12 1 0.404802 0.534240 0.412433 11.00000 0.01645 0.02051 = 0.02327 -0.00039 0.00363 -0.00022 REM AFIX 23 H12A 2 0.382196 0.447370 0.421606 11.00000 0.01724 H12B 2 0.311144 0.576565 0.404551 11.00000 0.02021 REM AFIX 0 C13 1 0.799801 0.468166 0.406730 11.00000 0.01842 0.01944 = 0.01316 -0.00017 -0.00015 -0.00088 C14 1 0.722705 0.356048 0.416441 11.00000 0.01665 0.01943 = 0.01928 0.00155 0.00090 -0.00046 REM AFIX 43 H14 2 0.621712 0.356317 0.427880 11.00000 0.02406 REM AFIX 0 C15 1 0.796085 0.241836 0.414461 11.00000 0.02176 0.01881 = 0.02052 0.00218 0.00028 -0.00148 REM AFIX 43 H15 2 0.737989 0.163071 0.419112 11.00000 0.02805 REM AFIX 0 C16 1 0.949136 0.237864 0.403850 11.00000 0.02283 0.02145 = 0.01942 0.00192 -0.00073 0.00444 REM AFIX 43 H16 2 1.001392 0.157136 0.403328 11.00000 0.02448 REM AFIX 0 C17 1 1.027863 0.348524 0.395508 11.00000 0.01637 0.02753 = 0.02047 0.00127 -0.00095 0.00271 REM AFIX 43 H17 2 1.134220 0.347119 0.390614 11.00000 0.02360 REM AFIX 0 C18 1 0.953612 0.462561 0.396530 11.00000 0.01853 0.02133 = 0.01795 -0.00034 0.00083 -0.00259 REM AFIX 43 H18 2 1.006981 0.539011 0.391639 11.00000 0.02424 REM AFIX 0 HKLF 4 REM JF2851CuFmi in P2(1)2(1)2(1) FINAL ALL DATA MERGE-I 3JUNE2019 REM wR2 = 0.0697, GooF = S = 1.065, Restrained GooF = 1.065 for all data REM R1 = 0.0262 for 2718 Fo > 4sig(Fo) and 0.0263 for all 2743 data REM 259 parameters refined using 0 restraints END WGHT 0.0425 0.2118 REM Instructions for potential hydrogen bonds HTAB C3 O1_$1 HTAB C4 O1_$1 REM Highest difference peak 0.252, deepest hole -0.156, 1-sigma level 0.034 Q1 1 0.6708 0.6039 0.3646 11.00000 0.05 0.25 Q2 1 0.6763 0.5986 0.4548 11.00000 0.05 0.22 Q3 1 0.6663 0.6100 0.2826 11.00000 0.05 0.22 Q4 1 0.5520 0.6115 0.4829 11.00000 0.05 0.19 Q5 1 0.5636 0.5723 0.4943 11.00000 0.05 0.19 Q6 1 0.5542 0.5836 0.3223 11.00000 0.05 0.18 Q7 1 0.4500 0.5662 0.4555 11.00000 0.05 0.17 Q8 1 0.8734 0.4602 0.3781 11.00000 0.05 0.17 Q9 1 0.6534 0.6109 0.1985 11.00000 0.05 0.16 Q10 1 0.8804 0.2472 0.4396 11.00000 0.05 0.15 Q11 1 0.8762 0.4653 0.4141 11.00000 0.05 0.14 Q12 1 0.4499 0.5687 0.5412 11.00000 0.05 0.14 Q13 1 0.4575 0.5927 0.6157 11.00000 0.05 0.14 Q14 1 0.8679 0.2405 0.3792 11.00000 0.05 0.13 Q15 1 0.7534 0.5345 0.4076 11.00000 0.05 0.13 Q16 1 0.4488 0.5478 0.2949 11.00000 0.05 0.12 Q17 1 0.4545 0.5385 0.3718 11.00000 0.05 0.12 Q18 1 0.5489 0.6515 0.6443 11.00000 0.05 0.12 Q19 1 0.9765 0.3027 0.3643 11.00000 0.05 0.12 Q20 1 0.4982 0.4955 0.3038 11.00000 0.05 0.12 ; _shelx_res_checksum 90385 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_JF2831FMI _database_code_depnum_ccdc_archive 'CCDC 1921674' loop_ _audit_author_name _audit_author_address 'James Fettinger' ;University of California, Davis United States of America ; _audit_update_record ; 2019-06-28 deposited with the CCDC. 2019-11-11 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 N O2' _chemical_formula_sum 'C23 H19 N O2' _chemical_formula_weight 341.39 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' N N 0.0311 0.0180 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.5431(2) _cell_length_b 17.2727(6) _cell_length_c 17.7127(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1695.89(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9462 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 72.09 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_F_000 720 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.214 _exptl_crystal_size_mid 0.106 _exptl_crystal_size_min 0.076 _exptl_absorpt_coefficient_mu 0.675 _shelx_estimated_absorpt_T_min 0.869 _shelx_estimated_absorpt_T_max 0.950 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8744 _exptl_absorpt_correction_T_max 0.9370 _exptl_absorpt_process_details 'SADABS 2016/2 (Sheldrick, 2016)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker Photon100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10237 _diffrn_reflns_av_unetI/netI 0.0158 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.574 _diffrn_reflns_theta_max 72.081 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 3335 _reflns_number_gt 3267 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.706 _reflns_Friedel_fraction_max 0.996 _reflns_Friedel_fraction_full 0.999 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Apex3 (2017.3) (Bruker, 2017)' _computing_cell_refinement 'SAINT (8.38a) (Bruker, 2017)' _computing_data_reduction 'SAINT (8.38a) (Bruker, 2017)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.3293P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_extinction_coef 0.0042(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.08(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 3335 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_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 C1 C 0.7252(3) 0.44513(9) 0.12222(8) 0.0143(3) Uani 1 1 d . . . . . H1 H 0.804(3) 0.4697(10) 0.0760(10) 0.008(4) Uiso 1 1 d . . . . . O1 O 0.4745(2) 0.46443(6) 0.12087(6) 0.0154(2) Uani 1 1 d . . . . . C2 C 0.8445(3) 0.48384(9) 0.19197(9) 0.0136(3) Uani 1 1 d . . . . . H2 H 1.009(4) 0.4745(11) 0.1857(11) 0.012(4) Uiso 1 1 d . . . . . C3 C 0.7938(3) 0.57032(8) 0.18826(8) 0.0139(3) Uani 1 1 d . . . . . C4 C 0.5973(3) 0.59820(9) 0.14748(8) 0.0142(3) Uani 1 1 d . . . . . C5 C 0.4419(3) 0.54412(9) 0.10133(9) 0.0160(3) Uani 1 1 d . . . . . H5A H 0.269(4) 0.5576(11) 0.1094(11) 0.019(5) Uiso 1 1 d . . . . . H5B H 0.481(4) 0.5509(10) 0.0470(10) 0.010(4) Uiso 1 1 d . . . . . C6 C 0.5462(3) 0.67739(9) 0.14714(9) 0.0159(3) Uani 1 1 d . . . . . H6 H 0.414(4) 0.6963(11) 0.1190(11) 0.018(5) Uiso 1 1 d . . . . . C7 C 0.6926(3) 0.72839(9) 0.18625(9) 0.0161(3) Uani 1 1 d . . . . . H7 H 0.657(4) 0.7828(12) 0.1860(11) 0.016(5) Uiso 1 1 d . . . . . C8 C 0.8923(3) 0.70120(9) 0.22602(9) 0.0164(3) Uani 1 1 d . . . . . H8 H 0.993(4) 0.7368(11) 0.2522(11) 0.019(5) Uiso 1 1 d . . . . . C9 C 0.9410(3) 0.62245(9) 0.22708(8) 0.0154(3) Uani 1 1 d . . . . . H9 H 1.074(4) 0.6042(11) 0.2544(12) 0.019(5) Uiso 1 1 d . . . . . C10 C 0.7526(3) 0.35823(8) 0.11718(8) 0.0144(3) Uani 1 1 d . . . . . C11 C 0.5795(3) 0.30786(9) 0.14698(9) 0.0161(3) Uani 1 1 d . . . . . H11 H 0.439(4) 0.3285(11) 0.1728(11) 0.017(5) Uiso 1 1 d . . . . . C12 C 0.6061(3) 0.22835(9) 0.14017(9) 0.0166(3) Uani 1 1 d . . . . . H12 H 0.488(4) 0.1936(12) 0.1625(12) 0.019(5) Uiso 1 1 d . . . . . C13 C 0.8056(3) 0.19753(9) 0.10330(8) 0.0142(3) Uani 1 1 d . . . . . O13 O 0.8166(2) 0.11828(6) 0.10054(6) 0.0173(2) Uani 1 1 d . . . . . C14 C 0.9804(3) 0.24677(9) 0.07291(8) 0.0160(3) Uani 1 1 d . . . . . H14 H 1.118(4) 0.2268(12) 0.0466(11) 0.020(5) Uiso 1 1 d . . . . . C15 C 0.9510(3) 0.32671(9) 0.08031(9) 0.0161(3) Uani 1 1 d . . . . . H15 H 1.069(5) 0.3604(13) 0.0592(12) 0.029(6) Uiso 1 1 d . . . . . C16 C 1.0348(3) 0.08528(9) 0.07188(10) 0.0201(3) Uani 1 1 d . . . . . H16A H 1.177(4) 0.1047(13) 0.0984(13) 0.027(6) Uiso 1 1 d . . . . . H16B H 1.048(4) 0.0975(12) 0.0182(12) 0.025(5) Uiso 1 1 d . . . . . H16C H 1.024(4) 0.0290(13) 0.0825(12) 0.026(5) Uiso 1 1 d . . . . . C17 C 0.7634(3) 0.44941(8) 0.26673(8) 0.0137(3) Uani 1 1 d . . . . . C18 C 0.5549(3) 0.47496(9) 0.30336(9) 0.0170(3) Uani 1 1 d . . . . . H18 H 0.455(4) 0.5171(12) 0.2822(12) 0.021(5) Uiso 1 1 d . . . . . C19 C 0.4844(3) 0.44277(9) 0.37167(9) 0.0173(3) Uani 1 1 d . . . . . H19 H 0.340(4) 0.4604(12) 0.3959(12) 0.025(5) Uiso 1 1 d . . . . . C20 C 0.6217(3) 0.38377(9) 0.40418(9) 0.0155(3) Uani 1 1 d . . . . . C21 C 0.8327(3) 0.35795(9) 0.36914(9) 0.0161(3) Uani 1 1 d . . . . . H21 H 0.930(4) 0.3162(12) 0.3922(12) 0.021(5) Uiso 1 1 d . . . . . C22 C 0.9006(3) 0.39135(9) 0.30085(9) 0.0148(3) Uani 1 1 d . . . . . H22 H 1.047(4) 0.3748(11) 0.2763(11) 0.018(5) Uiso 1 1 d . . . . . C23 C 0.5379(3) 0.34795(9) 0.47341(9) 0.0182(3) Uani 1 1 d . . . . . N23 N 0.4648(3) 0.31932(9) 0.52717(8) 0.0250(3) Uani 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 C1 0.0136(7) 0.0147(7) 0.0147(7) 0.0012(6) 0.0002(6) -0.0005(6) O1 0.0134(5) 0.0124(5) 0.0205(5) 0.0002(4) -0.0022(4) -0.0002(4) C2 0.0120(7) 0.0130(7) 0.0159(7) 0.0001(5) -0.0002(6) 0.0002(5) C3 0.0143(7) 0.0147(7) 0.0126(7) 0.0018(5) 0.0031(6) -0.0001(6) C4 0.0136(7) 0.0153(7) 0.0136(7) 0.0009(5) 0.0020(6) -0.0006(6) C5 0.0157(7) 0.0148(7) 0.0175(7) 0.0010(6) -0.0029(6) 0.0009(6) C6 0.0155(7) 0.0165(7) 0.0158(7) 0.0020(5) -0.0005(6) 0.0004(6) C7 0.0198(8) 0.0111(7) 0.0175(7) 0.0018(6) 0.0017(6) 0.0003(6) C8 0.0187(8) 0.0157(7) 0.0148(7) -0.0001(6) -0.0003(6) -0.0037(6) C9 0.0148(7) 0.0178(7) 0.0134(6) 0.0020(5) -0.0001(6) -0.0008(6) C10 0.0165(7) 0.0145(7) 0.0120(6) 0.0002(5) -0.0030(6) -0.0007(6) C11 0.0144(7) 0.0182(7) 0.0156(7) -0.0006(6) 0.0012(6) 0.0007(6) C12 0.0166(8) 0.0172(7) 0.0161(7) 0.0013(6) 0.0010(6) -0.0040(6) C13 0.0169(7) 0.0137(7) 0.0121(6) -0.0008(5) -0.0036(6) -0.0010(6) O13 0.0179(5) 0.0138(5) 0.0203(5) -0.0013(4) 0.0012(5) -0.0005(4) C14 0.0160(8) 0.0173(7) 0.0149(7) 0.0005(5) 0.0018(6) 0.0012(6) C15 0.0150(7) 0.0170(7) 0.0161(7) 0.0022(5) 0.0009(6) -0.0022(6) C16 0.0231(9) 0.0147(7) 0.0225(8) -0.0009(6) 0.0047(7) 0.0029(7) C17 0.0142(7) 0.0122(6) 0.0146(7) -0.0011(5) -0.0024(6) -0.0024(6) C18 0.0166(8) 0.0145(7) 0.0200(7) 0.0016(6) -0.0006(6) 0.0017(6) C19 0.0145(7) 0.0182(7) 0.0193(7) -0.0017(6) 0.0022(6) 0.0007(6) C20 0.0167(7) 0.0147(7) 0.0151(7) -0.0010(6) -0.0005(6) -0.0036(6) C21 0.0185(8) 0.0133(7) 0.0165(7) 0.0004(6) -0.0024(6) 0.0005(6) C22 0.0141(7) 0.0135(7) 0.0168(7) -0.0017(5) 0.0008(6) 0.0007(6) C23 0.0180(8) 0.0183(7) 0.0181(7) -0.0017(6) -0.0014(6) 0.0004(6) N23 0.0259(8) 0.0292(8) 0.0198(7) 0.0038(6) 0.0042(6) 0.0013(6) _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 C1 O1 1.4294(18) . ? C1 C10 1.5113(19) . ? C1 C2 1.553(2) . ? C1 H1 1.021(19) . ? O1 C5 1.4307(17) . ? C2 C17 1.520(2) . ? C2 C3 1.521(2) . ? C2 H2 0.93(2) . ? C3 C4 1.393(2) . ? C3 C9 1.396(2) . ? C4 C6 1.397(2) . ? C4 C5 1.511(2) . ? C5 H5A 1.00(2) . ? C5 H5B 0.992(19) . ? C6 C7 1.384(2) . ? C6 H6 0.95(2) . ? C7 C8 1.393(2) . ? C7 H7 0.96(2) . ? C8 C9 1.387(2) . ? C8 H8 0.95(2) . ? C9 H9 0.94(2) . ? C10 C15 1.390(2) . ? C10 C11 1.399(2) . ? C11 C12 1.387(2) . ? C11 H11 0.97(2) . ? C12 C13 1.391(2) . ? C12 H12 0.97(2) . ? C13 O13 1.3711(18) . ? C13 C14 1.397(2) . ? O13 C16 1.430(2) . ? C14 C15 1.396(2) . ? C14 H14 0.96(2) . ? C15 H15 0.95(2) . ? C16 H16A 0.98(2) . ? C16 H16B 0.98(2) . ? C16 H16C 0.99(2) . ? C17 C22 1.396(2) . ? C17 C18 1.397(2) . ? C18 C19 1.388(2) . ? C18 H18 0.99(2) . ? C19 C20 1.396(2) . ? C19 H19 0.96(2) . ? C20 C21 1.397(2) . ? C20 C23 1.450(2) . ? C21 C22 1.392(2) . ? C21 H21 0.99(2) . ? C22 H22 0.96(2) . ? C23 N23 1.147(2) . ? 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 O1 C1 C10 109.16(12) . . ? O1 C1 C2 109.10(12) . . ? C10 C1 C2 115.59(12) . . ? O1 C1 H1 107.9(10) . . ? C10 C1 H1 108.8(10) . . ? C2 C1 H1 106.0(10) . . ? C1 O1 C5 110.55(11) . . ? C17 C2 C3 111.54(12) . . ? C17 C2 C1 113.49(12) . . ? C3 C2 C1 108.04(12) . . ? C17 C2 H2 108.9(12) . . ? C3 C2 H2 110.2(12) . . ? C1 C2 H2 104.3(12) . . ? C4 C3 C9 119.30(14) . . ? C4 C3 C2 120.42(14) . . ? C9 C3 C2 120.27(14) . . ? C3 C4 C6 119.96(14) . . ? C3 C4 C5 120.84(13) . . ? C6 C4 C5 119.17(14) . . ? O1 C5 C4 113.08(12) . . ? O1 C5 H5A 108.1(11) . . ? C4 C5 H5A 109.1(12) . . ? O1 C5 H5B 108.7(10) . . ? C4 C5 H5B 109.2(11) . . ? H5A C5 H5B 108.6(16) . . ? C7 C6 C4 120.15(15) . . ? C7 C6 H6 119.9(12) . . ? C4 C6 H6 119.9(12) . . ? C6 C7 C8 120.29(14) . . ? C6 C7 H7 120.0(12) . . ? C8 C7 H7 119.7(12) . . ? C9 C8 C7 119.48(15) . . ? C9 C8 H8 120.8(12) . . ? C7 C8 H8 119.7(12) . . ? C8 C9 C3 120.80(15) . . ? C8 C9 H9 119.4(12) . . ? C3 C9 H9 119.8(12) . . ? C15 C10 C11 118.45(14) . . ? C15 C10 C1 119.74(14) . . ? C11 C10 C1 121.78(14) . . ? C12 C11 C10 120.69(15) . . ? C12 C11 H11 119.3(11) . . ? C10 C11 H11 120.0(11) . . ? C11 C12 C13 120.30(15) . . ? C11 C12 H12 120.4(12) . . ? C13 C12 H12 119.3(12) . . ? O13 C13 C12 115.73(14) . . ? O13 C13 C14 124.30(14) . . ? C12 C13 C14 119.97(14) . . ? C13 O13 C16 116.61(12) . . ? C15 C14 C13 119.02(14) . . ? C15 C14 H14 119.7(12) . . ? C13 C14 H14 121.3(12) . . ? C10 C15 C14 121.56(14) . . ? C10 C15 H15 119.2(14) . . ? C14 C15 H15 119.2(14) . . ? O13 C16 H16A 112.0(13) . . ? O13 C16 H16B 108.8(13) . . ? H16A C16 H16B 109.5(19) . . ? O13 C16 H16C 105.8(14) . . ? H16A C16 H16C 107.2(19) . . ? H16B C16 H16C 113.6(17) . . ? C22 C17 C18 118.45(14) . . ? C22 C17 C2 119.80(14) . . ? C18 C17 C2 121.74(13) . . ? C19 C18 C17 120.76(14) . . ? C19 C18 H18 118.0(13) . . ? C17 C18 H18 121.2(13) . . ? C18 C19 C20 119.92(15) . . ? C18 C19 H19 119.9(13) . . ? C20 C19 H19 120.2(13) . . ? C19 C20 C21 120.39(14) . . ? C19 C20 C23 119.08(15) . . ? C21 C20 C23 120.50(14) . . ? C22 C21 C20 118.69(14) . . ? C22 C21 H21 120.9(13) . . ? C20 C21 H21 120.4(12) . . ? C21 C22 C17 121.78(15) . . ? C21 C22 H22 119.8(12) . . ? C17 C22 H22 118.4(12) . . ? N23 C23 C20 177.88(19) . . ? 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 C10 C1 O1 C5 -161.47(11) . . . . ? C2 C1 O1 C5 71.35(14) . . . . ? O1 C1 C2 C17 68.87(15) . . . . ? C10 C1 C2 C17 -54.56(18) . . . . ? O1 C1 C2 C3 -55.36(15) . . . . ? C10 C1 C2 C3 -178.80(13) . . . . ? C17 C2 C3 C4 -102.21(16) . . . . ? C1 C2 C3 C4 23.18(19) . . . . ? C17 C2 C3 C9 76.41(18) . . . . ? C1 C2 C3 C9 -158.19(13) . . . . ? C9 C3 C4 C6 -1.4(2) . . . . ? C2 C3 C4 C6 177.20(14) . . . . ? C9 C3 C4 C5 176.65(13) . . . . ? C2 C3 C4 C5 -4.7(2) . . . . ? C1 O1 C5 C4 -49.74(16) . . . . ? C3 C4 C5 O1 16.4(2) . . . . ? C6 C4 C5 O1 -165.47(13) . . . . ? C3 C4 C6 C7 1.0(2) . . . . ? C5 C4 C6 C7 -177.09(14) . . . . ? C4 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C9 -1.0(2) . . . . ? C7 C8 C9 C3 0.6(2) . . . . ? C4 C3 C9 C8 0.6(2) . . . . ? C2 C3 C9 C8 -178.01(14) . . . . ? O1 C1 C10 C15 147.26(14) . . . . ? C2 C1 C10 C15 -89.34(17) . . . . ? O1 C1 C10 C11 -30.97(19) . . . . ? C2 C1 C10 C11 92.43(18) . . . . ? C15 C10 C11 C12 0.3(2) . . . . ? C1 C10 C11 C12 178.57(14) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 O13 179.14(14) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 O13 C16 -171.99(13) . . . . ? C14 C13 O13 C16 7.1(2) . . . . ? O13 C13 C14 C15 -179.00(14) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C11 C10 C15 C14 -0.3(2) . . . . ? C1 C10 C15 C14 -178.54(14) . . . . ? C13 C14 C15 C10 0.1(2) . . . . ? C3 C2 C17 C22 -142.70(14) . . . . ? C1 C2 C17 C22 94.98(16) . . . . ? C3 C2 C17 C18 36.5(2) . . . . ? C1 C2 C17 C18 -85.85(17) . . . . ? C22 C17 C18 C19 -0.7(2) . . . . ? C2 C17 C18 C19 -179.89(14) . . . . ? C17 C18 C19 C20 -0.5(2) . . . . ? C18 C19 C20 C21 1.4(2) . . . . ? C18 C19 C20 C23 -176.62(15) . . . . ? C19 C20 C21 C22 -1.0(2) . . . . ? C23 C20 C21 C22 176.93(15) . . . . ? C20 C21 C22 C17 -0.2(2) . . . . ? C18 C17 C22 C21 1.1(2) . . . . ? C2 C17 C22 C21 -179.75(14) . . . . ? _refine_diff_density_max 0.195 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.031 _shelx_res_file ; TITL JF2831Fmi in P2(1)2(1)2(1) FINAL ALL DATA MEGE-I 26MAR2019 JF2831FMI.res created by SHELXL-2018/3 at 14:09:59 on 26-Mar-2019 CELL 1.54178 5.5431 17.2727 17.7127 90.0000 90.0000 90.0000 ZERR 4.00 0.0002 0.0006 0.0006 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O UNIT 92 76 4 8 L.S. 9 HTAB WPDB -2 CONF ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.076 0.106 0.214 TEMP -173. WGHT 0.037800 0.329300 EXTI 0.004220 FVAR 0.24004 C1 1 0.725186 0.445130 0.122223 11.00000 0.01363 0.01471 = 0.01468 0.00116 0.00023 -0.00047 REM AFIX 13 H1 2 0.804260 0.469690 0.076029 11.00000 0.00786 REM AFIX 0 O1 4 0.474458 0.464430 0.120871 11.00000 0.01344 0.01238 = 0.02047 0.00023 -0.00218 -0.00016 C2 1 0.844529 0.483843 0.191968 11.00000 0.01196 0.01302 = 0.01589 0.00008 -0.00020 0.00021 REM AFIX 13 H2 2 1.009064 0.474463 0.185735 11.00000 0.01227 REM AFIX 0 C3 1 0.793815 0.570318 0.188260 11.00000 0.01427 0.01473 = 0.01259 0.00182 0.00310 -0.00012 C4 1 0.597305 0.598196 0.147483 11.00000 0.01364 0.01533 = 0.01360 0.00093 0.00201 -0.00064 C5 1 0.441922 0.544115 0.101326 11.00000 0.01573 0.01483 = 0.01748 0.00100 -0.00293 0.00089 REM AFIX 23 H5A 2 0.268781 0.557601 0.109361 11.00000 0.01891 H5B 2 0.480535 0.550885 0.047028 11.00000 0.01044 REM AFIX 0 C6 1 0.546166 0.677388 0.147141 11.00000 0.01547 0.01646 = 0.01583 0.00196 -0.00053 0.00041 REM AFIX 43 H6 2 0.413844 0.696316 0.118969 11.00000 0.01816 REM AFIX 0 C7 1 0.692583 0.728391 0.186254 11.00000 0.01975 0.01113 = 0.01754 0.00179 0.00174 0.00033 REM AFIX 43 H7 2 0.656943 0.782833 0.185962 11.00000 0.01579 REM AFIX 0 C8 1 0.892258 0.701204 0.226024 11.00000 0.01869 0.01574 = 0.01476 -0.00011 -0.00029 -0.00368 REM AFIX 43 H8 2 0.992967 0.736773 0.252222 11.00000 0.01859 REM AFIX 0 C9 1 0.940997 0.622452 0.227084 11.00000 0.01484 0.01780 = 0.01343 0.00196 -0.00008 -0.00079 REM AFIX 43 H9 2 1.074036 0.604188 0.254440 11.00000 0.01928 REM AFIX 0 C10 1 0.752562 0.358232 0.117182 11.00000 0.01654 0.01453 = 0.01202 0.00022 -0.00299 -0.00070 C11 1 0.579474 0.307864 0.146978 11.00000 0.01438 0.01819 = 0.01560 -0.00064 0.00124 0.00069 REM AFIX 43 H11 2 0.438876 0.328465 0.172785 11.00000 0.01690 REM AFIX 0 C12 1 0.606061 0.228352 0.140175 11.00000 0.01656 0.01721 = 0.01607 0.00126 0.00099 -0.00400 REM AFIX 43 H12 2 0.488162 0.193568 0.162521 11.00000 0.01878 REM AFIX 0 C13 1 0.805632 0.197535 0.103298 11.00000 0.01687 0.01367 = 0.01209 -0.00083 -0.00358 -0.00097 O13 4 0.816575 0.118284 0.100541 11.00000 0.01785 0.01375 = 0.02026 -0.00127 0.00123 -0.00046 C14 1 0.980351 0.246769 0.072911 11.00000 0.01596 0.01728 = 0.01486 0.00050 0.00185 0.00116 REM AFIX 43 H14 2 1.117718 0.226789 0.046621 11.00000 0.01994 REM AFIX 0 C15 1 0.951019 0.326709 0.080308 11.00000 0.01504 0.01704 = 0.01608 0.00219 0.00089 -0.00224 REM AFIX 43 H15 2 1.068866 0.360395 0.059156 11.00000 0.02896 REM AFIX 0 C16 1 1.034813 0.085284 0.071883 11.00000 0.02314 0.01474 = 0.02253 -0.00086 0.00468 0.00289 REM AFIX 137 H16A 2 1.176852 0.104705 0.098381 11.00000 0.02695 H16B 2 1.047955 0.097459 0.018161 11.00000 0.02456 H16C 2 1.023848 0.028996 0.082490 11.00000 0.02623 REM AFIX 0 C17 1 0.763360 0.449415 0.266725 11.00000 0.01418 0.01219 = 0.01461 -0.00108 -0.00240 -0.00239 C18 1 0.554942 0.474962 0.303358 11.00000 0.01661 0.01447 = 0.01998 0.00164 -0.00064 0.00172 REM AFIX 43 H18 2 0.455391 0.517067 0.282172 11.00000 0.02110 REM AFIX 0 C19 1 0.484445 0.442771 0.371670 11.00000 0.01450 0.01817 = 0.01933 -0.00168 0.00216 0.00070 REM AFIX 43 H19 2 0.340412 0.460404 0.395892 11.00000 0.02469 REM AFIX 0 C20 1 0.621663 0.383765 0.404182 11.00000 0.01668 0.01470 = 0.01511 -0.00098 -0.00046 -0.00358 C21 1 0.832709 0.357952 0.369143 11.00000 0.01855 0.01334 = 0.01649 0.00041 -0.00237 0.00045 REM AFIX 43 H21 2 0.930096 0.316163 0.392204 11.00000 0.02120 REM AFIX 0 C22 1 0.900589 0.391349 0.300854 11.00000 0.01410 0.01351 = 0.01685 -0.00173 0.00080 0.00071 REM AFIX 43 H22 2 1.046585 0.374778 0.276282 11.00000 0.01759 REM AFIX 0 C23 1 0.537945 0.347950 0.473406 11.00000 0.01800 0.01833 = 0.01815 -0.00173 -0.00142 0.00043 N23 3 0.464817 0.319324 0.527172 11.00000 0.02587 0.02918 = 0.01982 0.00379 0.00419 0.00130 HKLF 4 REM JF2831Fmi in P2(1)2(1)2(1) FINAL ALL DATA MEGE-I 26MAR2019 REM wR2 = 0.0651, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0250 for 3267 Fo > 4sig(Fo) and 0.0258 for all 3335 data REM 312 parameters refined using 0 restraints END WGHT 0.0378 0.3293 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.195, deepest hole -0.160, 1-sigma level 0.031 Q1 1 0.7907 0.4610 0.1590 11.00000 0.05 0.20 Q2 1 0.7490 0.3988 0.1186 11.00000 0.05 0.19 Q3 1 0.6343 0.3355 0.1137 11.00000 0.05 0.16 Q4 1 0.9204 0.2218 0.0984 11.00000 0.05 0.16 Q5 1 0.5364 0.5715 0.1230 11.00000 0.05 0.16 Q6 1 0.8932 0.3412 0.1148 11.00000 0.05 0.15 Q7 1 0.7941 0.4612 0.2273 11.00000 0.05 0.15 Q8 1 0.6972 0.3341 0.1426 11.00000 0.05 0.15 Q9 1 0.7367 0.5820 0.1440 11.00000 0.05 0.15 Q10 1 0.8269 0.5296 0.1852 11.00000 0.05 0.15 Q11 1 0.6436 0.5806 0.1831 11.00000 0.05 0.13 Q12 1 0.6528 0.7017 0.1541 11.00000 0.05 0.13 Q13 1 0.8339 0.5982 0.2226 11.00000 0.05 0.13 Q14 1 0.8054 0.3439 0.0838 11.00000 0.05 0.13 Q15 1 0.5298 0.6302 0.1621 11.00000 0.05 0.12 Q16 1 0.8786 0.3860 0.3388 11.00000 0.05 0.12 Q17 1 0.5314 0.4021 0.3767 11.00000 0.05 0.12 Q18 1 0.5999 0.2670 0.1231 11.00000 0.05 0.12 Q19 1 0.7504 0.7102 0.2175 11.00000 0.05 0.12 Q20 1 0.7525 0.2169 0.1401 11.00000 0.05 0.12 ; _shelx_res_checksum 42689