#------------------------------------------------------------------------------ #$Date: 2019-11-17 15:28:34 +0200 (Sun, 17 Nov 2019) $ #$Revision: 230884 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156042.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7156042 loop_ _publ_author_name 'Shoji, Taku' 'Tanaka, Miwa' 'Takagaki, Sho' 'Miura, Kota' 'Ohta, Akira' 'Sekiguchi, Ryuta' 'Ito, Shunji' 'Mori, Shigeki' 'Okujima, Tetsuo' _publ_section_title ; Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties. ; _journal_issue 3 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 480 _journal_page_last 489 _journal_paper_doi 10.1039/c7ob02861j _journal_volume 16 _journal_year 2018 _chemical_formula_moiety 'C21 H13 I O4' _chemical_formula_sum 'C21 H13 I O4' _chemical_formula_weight 456.21 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2017-04-18 deposited with the CCDC. 2017-12-21 downloaded from the CCDC. ; _cell_angle_alpha 103.6260(17) _cell_angle_beta 100.7920(17) _cell_angle_gamma 99.5738(17) _cell_formula_units_Z 4 _cell_length_a 7.76154(16) _cell_length_b 14.0693(3) _cell_length_c 16.6303(3) _cell_measurement_reflns_used 18691 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.26 _cell_measurement_theta_min 1.75 _cell_volume 1691.05(6) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2.4 (Rigaku, 2016)' _computing_publication_material 'CrystalStructure 4.2.4' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_unetI/netI 0.0439 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 28239 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.996 _diffrn_reflns_theta_min 2.259 _diffrn_source 'Varimax 50 kV 24 mA Rotating anode' _exptl_absorpt_coefficient_mu 1.918 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.040 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.020 _refine_diff_density_max 1.813 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.115 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 471 _refine_ls_number_reflns 8138 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0332 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+2.4452P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.0719 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6953 _reflns_number_total 8138 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02861j2.cif _cod_data_source_block shelxl_CCDC2 _cod_depositor_comments 'Adding full bibliography for 7156040--7156045.cif.' _cod_database_code 7156042 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.927 _shelx_estimated_absorpt_t_max 0.963 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2016/6 at 22:55:24 on 04-Apr-2017 CELL 0.71075 7.76154 14.06930 16.63030 103.62600 100.79200 99.57380 ZERR 4 0.00016 0.00030 0.00030 0.00170 0.00170 0.00170 LATT 1 SFAC C H I O UNIT 84 52 4 16 SHEL 99999.000000 0.756965 OMIT 0 1 0 OMIT 0 -1 1 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.040 0.020 0.020 WGHT 0.025800 2.445200 FVAR 0.35702 I1 3 -0.101773 0.537609 0.623229 11.00000 0.01605 0.01555 = 0.01300 0.00574 -0.00178 0.00079 I2 3 0.573527 0.167413 0.924191 11.00000 0.01473 0.01864 = 0.01109 0.00215 0.00363 0.00458 O1 4 0.092486 1.075590 0.790128 11.00000 0.02510 0.01020 = 0.01911 0.00370 0.00297 0.00517 O2 4 0.099965 1.014073 0.903561 11.00000 0.02005 0.01102 = 0.01727 0.00321 0.00847 0.00622 O3 4 0.311461 0.669769 0.854469 11.00000 0.01937 0.01088 = 0.00997 0.00313 0.00052 0.00439 O4 4 0.459934 0.619594 0.956518 11.00000 0.03045 0.02049 = 0.01221 0.00293 -0.00098 0.00940 O5 4 0.694220 0.592958 0.818014 11.00000 0.03347 0.01055 = 0.01905 0.00564 0.00346 0.00414 O6 4 0.860171 0.525508 0.906196 11.00000 0.02282 0.01317 = 0.01541 -0.00198 -0.00518 0.00030 O7 4 0.664548 0.095027 0.670917 11.00000 0.02373 0.01129 = 0.01273 0.00480 0.00615 0.00787 O8 4 0.740220 -0.028266 0.586337 11.00000 0.04815 0.01773 = 0.01673 0.00736 0.01719 0.01636 C1 1 0.146447 0.911633 0.781688 11.00000 0.01150 0.01101 = 0.01184 0.00402 0.00123 0.00157 C2 1 0.148089 0.830943 0.817318 11.00000 0.01036 0.01199 = 0.01148 0.00493 0.00272 0.00173 AFIX 43 H2 2 0.131886 0.831725 0.872675 11.00000 -1.20000 AFIX 0 C3 1 0.177299 0.748558 0.758955 11.00000 0.01188 0.00938 = 0.01355 0.00238 0.00256 0.00301 C4 1 0.204719 0.778352 0.686167 11.00000 0.01031 0.01080 = 0.01202 0.00377 0.00036 0.00135 C5 1 0.260101 0.721993 0.618896 11.00000 0.01333 0.01219 = 0.01648 0.00404 0.00281 0.00090 AFIX 43 H5 2 0.278051 0.658148 0.623539 11.00000 -1.20000 AFIX 0 C6 1 0.292816 0.746114 0.545844 11.00000 0.01813 0.01655 = 0.01492 -0.00009 0.00480 -0.00102 AFIX 43 H6 2 0.335890 0.698161 0.508817 11.00000 -1.20000 AFIX 0 C7 1 0.270617 0.831424 0.519962 11.00000 0.02137 0.02418 = 0.01288 0.00496 0.00593 0.00026 AFIX 43 H7 2 0.293856 0.831759 0.465926 11.00000 -1.20000 AFIX 0 C8 1 0.219808 0.915455 0.561387 11.00000 0.02557 0.01943 = 0.01491 0.01078 0.00200 -0.00058 AFIX 43 H8 2 0.209260 0.964233 0.530869 11.00000 -1.20000 AFIX 0 C9 1 0.181544 0.939467 0.641618 11.00000 0.01798 0.01335 = 0.01721 0.00576 0.00150 0.00226 AFIX 43 H9 2 0.153960 1.003344 0.659169 11.00000 -1.20000 AFIX 0 C10 1 0.178575 0.882175 0.699022 11.00000 0.01058 0.01205 = 0.01404 0.00572 0.00055 0.00213 C11 1 0.111406 1.008418 0.822677 11.00000 0.00902 0.01247 = 0.01452 0.00317 0.00049 0.00043 C12 1 0.069463 1.108077 0.950529 11.00000 0.02170 0.01573 = 0.02114 0.00033 0.00763 0.00614 AFIX 137 H12A 2 -0.030592 1.126088 0.916226 11.00000 -1.20000 H12B 2 0.178329 1.160847 0.963232 11.00000 -1.20000 H12C 2 0.040035 1.100836 1.003878 11.00000 -1.20000 AFIX 0 C13 1 0.189632 0.653145 0.776845 11.00000 0.01431 0.01607 = 0.00914 0.00508 0.00409 0.00696 C14 1 0.352208 0.594908 0.889585 11.00000 0.01711 0.02511 = 0.01122 0.01136 0.00463 0.01051 C15 1 0.259036 0.491601 0.840365 11.00000 0.01287 0.01768 = 0.01191 0.00485 0.00533 0.00570 C16 1 0.299800 0.412929 0.872372 11.00000 0.01814 0.02185 = 0.01595 0.01104 0.00723 0.00956 AFIX 43 H16 2 0.385539 0.426306 0.924813 11.00000 -1.20000 AFIX 0 C17 1 0.214929 0.315343 0.827481 11.00000 0.02096 0.01591 = 0.02305 0.01227 0.01145 0.00857 AFIX 43 H17 2 0.242444 0.261549 0.849195 11.00000 -1.20000 AFIX 0 C18 1 0.089551 0.295467 0.750745 11.00000 0.01956 0.00987 = 0.02360 0.00534 0.01122 0.00556 AFIX 43 H18 2 0.032033 0.228146 0.720150 11.00000 -1.20000 AFIX 0 C19 1 0.047916 0.373561 0.718558 11.00000 0.01660 0.01383 = 0.01442 0.00449 0.00354 0.00337 AFIX 43 H19 2 -0.038427 0.359438 0.666197 11.00000 -1.20000 AFIX 0 C20 1 0.132462 0.472840 0.762846 11.00000 0.01236 0.01470 = 0.01535 0.00646 0.00743 0.00360 C21 1 0.099940 0.559518 0.732873 11.00000 0.01327 0.01630 = 0.00689 0.00419 0.00009 0.00567 C22 1 0.659064 0.414945 0.786587 11.00000 0.01178 0.01318 = 0.01266 0.00325 0.00450 0.00231 C23 1 0.704590 0.331394 0.809758 11.00000 0.01122 0.01569 = 0.01132 0.00118 0.00166 0.00508 AFIX 43 H23 2 0.789004 0.334277 0.860140 11.00000 -1.20000 AFIX 0 C24 1 0.609052 0.243683 0.748769 11.00000 0.01243 0.01413 = 0.01129 0.00540 0.00182 0.00343 C25 1 0.496924 0.270181 0.683568 11.00000 0.01463 0.01235 = 0.01177 0.00272 0.00608 0.00483 C26 1 0.374763 0.203016 0.612886 11.00000 0.01587 0.01239 = 0.01405 0.00214 0.00427 0.00598 AFIX 43 H26 2 0.372703 0.134111 0.607711 11.00000 -1.20000 AFIX 0 C27 1 0.254998 0.223017 0.548635 11.00000 0.01694 0.01653 = 0.01290 -0.00082 0.00007 0.00335 AFIX 43 H27 2 0.177622 0.165856 0.507435 11.00000 -1.20000 AFIX 0 C28 1 0.233298 0.315040 0.536603 11.00000 0.02070 0.02413 = 0.01093 0.00429 0.00098 0.00871 AFIX 43 H28 2 0.144114 0.311962 0.487814 11.00000 -1.20000 AFIX 0 C29 1 0.323577 0.411323 0.585829 11.00000 0.02053 0.01862 = 0.01580 0.01015 0.00574 0.01041 AFIX 43 H29 2 0.292492 0.464341 0.563913 11.00000 -1.20000 AFIX 0 C30 1 0.452678 0.440837 0.662458 11.00000 0.01665 0.01127 = 0.01278 0.00195 0.00432 0.00296 AFIX 43 H30 2 0.493816 0.511134 0.686955 11.00000 -1.20000 AFIX 0 C31 1 0.529667 0.380873 0.708054 11.00000 0.01235 0.01259 = 0.01279 0.00291 0.00563 0.00357 C32 1 0.734185 0.519653 0.835837 11.00000 0.01634 0.01258 = 0.01367 0.00242 0.00745 0.00214 C33 1 0.941355 0.626498 0.959204 11.00000 0.03598 0.01729 = 0.01893 -0.00147 -0.00183 -0.00504 AFIX 137 H33A 2 0.850230 0.656209 0.983251 11.00000 -1.20000 H33B 2 0.990258 0.667016 0.924762 11.00000 -1.20000 H33C 2 1.038516 0.624613 1.005471 11.00000 -1.20000 AFIX 0 C34 1 0.629014 0.141276 0.747930 11.00000 0.01419 0.01022 = 0.01385 -0.00039 0.00459 0.00416 C35 1 0.698446 0.000600 0.652556 11.00000 0.01777 0.01176 = 0.01486 0.00251 0.00375 0.00451 C36 1 0.678447 -0.056082 0.714642 11.00000 0.01301 0.01223 = 0.01476 0.00423 0.00240 0.00112 C37 1 0.702453 -0.154025 0.696181 11.00000 0.01499 0.01283 = 0.01967 0.00438 0.00396 0.00326 AFIX 43 H37 2 0.729991 -0.182761 0.643726 11.00000 -1.20000 AFIX 0 C38 1 0.686564 -0.209560 0.753424 11.00000 0.01519 0.00972 = 0.02355 0.00685 -0.00198 0.00218 AFIX 43 H38 2 0.702789 -0.276474 0.740671 11.00000 -1.20000 AFIX 0 C39 1 0.646409 -0.166662 0.830347 11.00000 0.01225 0.01715 = 0.02239 0.01145 -0.00151 -0.00112 AFIX 43 H39 2 0.634191 -0.205092 0.869698 11.00000 -1.20000 AFIX 0 C40 1 0.624172 -0.069261 0.850134 11.00000 0.01369 0.01641 = 0.01638 0.00578 0.00252 0.00203 AFIX 43 H40 2 0.597835 -0.041294 0.903068 11.00000 -1.20000 AFIX 0 C41 1 0.640031 -0.011125 0.792951 11.00000 0.00877 0.01162 = 0.01300 0.00333 -0.00101 0.00033 C42 1 0.618184 0.092294 0.807533 11.00000 0.01241 0.01618 = 0.00767 0.00090 0.00138 0.00377 HKLF 4 REM xcalibur REM R1 = 0.0332 for 6953 Fo > 4sig(Fo) and 0.0418 for all 8138 data REM 471 parameters refined using 0 restraints END WGHT 0.0258 2.4450 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y+1, z HTAB C12 I2_$1 EQIV $2 x, y+1, z HTAB C12 I2_$2 REM Highest difference peak 1.813, deepest hole -0.508, 1-sigma level 0.115 Q1 1 0.3746 0.6626 0.9187 11.00000 0.05 1.81 Q2 1 0.7149 0.0547 0.6214 11.00000 0.05 0.97 Q3 1 -0.0492 0.4995 0.5652 11.00000 0.05 0.55 ; _shelx_res_checksum 69828 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 I1 I -0.10177(3) 0.53761(2) 0.62323(2) 0.01560(6) Uani 1 1 d . . I2 I 0.57353(3) 0.16741(2) 0.92419(2) 0.01497(6) Uani 1 1 d . . O1 O 0.0925(3) 1.07559(16) 0.79013(14) 0.0184(5) Uani 1 1 d . . O2 O 0.1000(3) 1.01407(15) 0.90356(14) 0.0153(5) Uani 1 1 d . . O3 O 0.3115(3) 0.66977(15) 0.85447(13) 0.0136(4) Uani 1 1 d . . O4 O 0.4599(3) 0.61959(17) 0.95652(14) 0.0217(5) Uani 1 1 d . . O5 O 0.6942(3) 0.59296(16) 0.81801(14) 0.0212(5) Uani 1 1 d . . O6 O 0.8602(3) 0.52551(16) 0.90620(14) 0.0200(5) Uani 1 1 d . . O7 O 0.6645(3) 0.09503(15) 0.67092(13) 0.0149(4) Uani 1 1 d . . O8 O 0.7402(4) -0.02827(17) 0.58634(14) 0.0247(6) Uani 1 1 d . . C1 C 0.1464(4) 0.9116(2) 0.78169(19) 0.0116(6) Uani 1 1 d . . C2 C 0.1481(4) 0.8309(2) 0.81732(19) 0.0110(6) Uani 1 1 d . . H2 H 0.131886 0.831725 0.872675 0.013 Uiso 1 1 calc R U C3 C 0.1773(4) 0.7486(2) 0.75896(19) 0.0117(6) Uani 1 1 d . . C4 C 0.2047(4) 0.7784(2) 0.68617(19) 0.0114(6) Uani 1 1 d . . C5 C 0.2601(4) 0.7220(2) 0.61890(19) 0.0143(6) Uani 1 1 d . . H5 H 0.278051 0.658148 0.623539 0.017 Uiso 1 1 calc R U C6 C 0.2928(4) 0.7461(2) 0.5458(2) 0.0178(7) Uani 1 1 d . . H6 H 0.335890 0.698161 0.508817 0.021 Uiso 1 1 calc R U C7 C 0.2706(4) 0.8314(2) 0.5200(2) 0.0198(7) Uani 1 1 d . . H7 H 0.293856 0.831759 0.465926 0.024 Uiso 1 1 calc R U C8 C 0.2198(4) 0.9155(2) 0.5614(2) 0.0200(7) Uani 1 1 d . . H8 H 0.209260 0.964233 0.530869 0.024 Uiso 1 1 calc R U C9 C 0.1815(4) 0.9395(2) 0.6416(2) 0.0164(6) Uani 1 1 d . . H9 H 0.153960 1.003344 0.659169 0.020 Uiso 1 1 calc R U C10 C 0.1786(4) 0.8822(2) 0.69902(19) 0.0122(6) Uani 1 1 d . . C11 C 0.1114(4) 1.0084(2) 0.82268(19) 0.0127(6) Uani 1 1 d . . C12 C 0.0695(4) 1.1081(2) 0.9505(2) 0.0198(7) Uani 1 1 d . . H12A H -0.030592 1.126088 0.916226 0.024 Uiso 1 1 calc R U H12B H 0.178329 1.160847 0.963232 0.024 Uiso 1 1 calc R U H12C H 0.040035 1.100836 1.003878 0.024 Uiso 1 1 calc R U C13 C 0.1896(4) 0.6531(2) 0.77685(18) 0.0123(6) Uani 1 1 d . . C14 C 0.3522(4) 0.5949(2) 0.88958(19) 0.0158(6) Uani 1 1 d . . C15 C 0.2590(4) 0.4916(2) 0.84037(19) 0.0134(6) Uani 1 1 d . . C16 C 0.2998(4) 0.4129(2) 0.8724(2) 0.0166(6) Uani 1 1 d . . H16 H 0.385539 0.426306 0.924813 0.020 Uiso 1 1 calc R U C17 C 0.2149(4) 0.3153(2) 0.8275(2) 0.0173(7) Uani 1 1 d . . H17 H 0.242444 0.261549 0.849195 0.021 Uiso 1 1 calc R U C18 C 0.0896(4) 0.2955(2) 0.7507(2) 0.0164(7) Uani 1 1 d . . H18 H 0.032033 0.228146 0.720150 0.020 Uiso 1 1 calc R U C19 C 0.0479(4) 0.3736(2) 0.7186(2) 0.0149(6) Uani 1 1 d . . H19 H -0.038427 0.359438 0.666197 0.018 Uiso 1 1 calc R U C20 C 0.1325(4) 0.4728(2) 0.76285(19) 0.0131(6) Uani 1 1 d . . C21 C 0.0999(4) 0.5595(2) 0.73287(18) 0.0120(6) Uani 1 1 d . . C22 C 0.6591(4) 0.4149(2) 0.78659(19) 0.0124(6) Uani 1 1 d . . C23 C 0.7046(4) 0.3314(2) 0.80976(19) 0.0131(6) Uani 1 1 d . . H23 H 0.789004 0.334277 0.860140 0.016 Uiso 1 1 calc R U C24 C 0.6091(4) 0.2437(2) 0.74877(19) 0.0124(6) Uani 1 1 d . . C25 C 0.4969(4) 0.2702(2) 0.68357(19) 0.0124(6) Uani 1 1 d . . C26 C 0.3748(4) 0.2030(2) 0.61289(19) 0.0139(6) Uani 1 1 d . . H26 H 0.372703 0.134111 0.607711 0.017 Uiso 1 1 calc R U C27 C 0.2550(4) 0.2230(2) 0.54864(19) 0.0168(6) Uani 1 1 d . . H27 H 0.177622 0.165856 0.507435 0.020 Uiso 1 1 calc R U C28 C 0.2333(4) 0.3150(2) 0.5366(2) 0.0186(7) Uani 1 1 d . . H28 H 0.144114 0.311962 0.487814 0.022 Uiso 1 1 calc R U C29 C 0.3236(4) 0.4113(2) 0.5858(2) 0.0164(6) Uani 1 1 d . . H29 H 0.292492 0.464341 0.563913 0.020 Uiso 1 1 calc R U C30 C 0.4527(4) 0.4408(2) 0.66246(19) 0.0137(6) Uani 1 1 d . . H30 H 0.493816 0.511134 0.686955 0.016 Uiso 1 1 calc R U C31 C 0.5297(4) 0.3809(2) 0.70805(19) 0.0122(6) Uani 1 1 d . . C32 C 0.7342(4) 0.5197(2) 0.83584(19) 0.0140(6) Uani 1 1 d . . C33 C 0.9414(5) 0.6265(3) 0.9592(2) 0.0277(8) Uani 1 1 d . . H33A H 0.850230 0.656209 0.983251 0.033 Uiso 1 1 calc R U H33B H 0.990258 0.667016 0.924762 0.033 Uiso 1 1 calc R U H33C H 1.038516 0.624613 1.005471 0.033 Uiso 1 1 calc R U C34 C 0.6290(4) 0.1413(2) 0.74793(19) 0.0130(6) Uani 1 1 d . . C35 C 0.6984(4) 0.0006(2) 0.6526(2) 0.0149(6) Uani 1 1 d . . C36 C 0.6784(4) -0.0561(2) 0.71464(19) 0.0136(6) Uani 1 1 d . . C37 C 0.7025(4) -0.1540(2) 0.6962(2) 0.0158(6) Uani 1 1 d . . H37 H 0.729991 -0.182761 0.643726 0.019 Uiso 1 1 calc R U C38 C 0.6866(4) -0.2096(2) 0.7534(2) 0.0167(7) Uani 1 1 d . . H38 H 0.702789 -0.276474 0.740671 0.020 Uiso 1 1 calc R U C39 C 0.6464(4) -0.1667(2) 0.8303(2) 0.0175(7) Uani 1 1 d . . H39 H 0.634191 -0.205092 0.869698 0.021 Uiso 1 1 calc R U C40 C 0.6242(4) -0.0693(2) 0.8501(2) 0.0156(6) Uani 1 1 d . . H40 H 0.597835 -0.041294 0.903068 0.019 Uiso 1 1 calc R U C41 C 0.6400(4) -0.0111(2) 0.79295(19) 0.0119(6) Uani 1 1 d . . C42 C 0.6182(4) 0.0923(2) 0.80753(18) 0.0126(6) 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 I1 0.01605(11) 0.01555(11) 0.01300(10) 0.00574(8) -0.00178(8) 0.00079(8) I2 0.01473(10) 0.01864(11) 0.01109(10) 0.00215(8) 0.00363(8) 0.00458(8) O1 0.0251(12) 0.0102(11) 0.0191(12) 0.0037(9) 0.0030(10) 0.0052(9) O2 0.0201(11) 0.0110(11) 0.0173(11) 0.0032(9) 0.0085(9) 0.0062(9) O3 0.0194(11) 0.0109(11) 0.0100(10) 0.0031(8) 0.0005(9) 0.0044(9) O4 0.0305(13) 0.0205(12) 0.0122(11) 0.0029(9) -0.0010(10) 0.0094(10) O5 0.0335(14) 0.0106(11) 0.0191(12) 0.0056(9) 0.0035(10) 0.0041(10) O6 0.0228(12) 0.0132(11) 0.0154(11) -0.0020(9) -0.0052(9) 0.0003(9) O7 0.0237(12) 0.0113(11) 0.0127(11) 0.0048(9) 0.0062(9) 0.0079(9) O8 0.0482(16) 0.0177(12) 0.0167(12) 0.0074(10) 0.0172(11) 0.0164(11) C1 0.0115(14) 0.0110(14) 0.0118(14) 0.0040(11) 0.0012(11) 0.0016(11) C2 0.0104(14) 0.0120(14) 0.0115(14) 0.0049(12) 0.0027(11) 0.0017(11) C3 0.0119(14) 0.0094(14) 0.0136(15) 0.0024(12) 0.0026(12) 0.0030(11) C4 0.0103(14) 0.0108(14) 0.0120(14) 0.0038(11) 0.0004(11) 0.0014(11) C5 0.0133(15) 0.0122(15) 0.0165(15) 0.0040(12) 0.0028(12) 0.0009(12) C6 0.0181(16) 0.0166(16) 0.0149(16) -0.0001(13) 0.0048(13) -0.0010(13) C7 0.0214(17) 0.0242(18) 0.0129(16) 0.0050(13) 0.0059(13) 0.0003(14) C8 0.0256(18) 0.0194(17) 0.0149(16) 0.0108(13) 0.0020(13) -0.0006(14) C9 0.0180(16) 0.0133(15) 0.0172(16) 0.0058(13) 0.0015(13) 0.0023(12) C10 0.0106(14) 0.0120(15) 0.0140(15) 0.0057(12) 0.0005(11) 0.0021(11) C11 0.0090(14) 0.0125(15) 0.0145(15) 0.0032(12) 0.0005(11) 0.0004(11) C12 0.0217(17) 0.0157(16) 0.0211(17) 0.0003(13) 0.0076(14) 0.0061(13) C13 0.0143(15) 0.0161(15) 0.0091(14) 0.0051(12) 0.0041(11) 0.0070(12) C14 0.0171(15) 0.0251(17) 0.0112(15) 0.0114(13) 0.0046(12) 0.0105(13) C15 0.0129(14) 0.0177(16) 0.0119(15) 0.0049(12) 0.0053(12) 0.0057(12) C16 0.0181(16) 0.0218(17) 0.0160(16) 0.0110(13) 0.0072(13) 0.0096(13) C17 0.0210(16) 0.0159(16) 0.0230(17) 0.0123(14) 0.0115(14) 0.0086(13) C18 0.0196(16) 0.0099(15) 0.0236(17) 0.0053(13) 0.0112(13) 0.0056(12) C19 0.0166(15) 0.0138(15) 0.0144(15) 0.0045(12) 0.0035(12) 0.0034(12) C20 0.0124(14) 0.0147(15) 0.0153(15) 0.0065(12) 0.0074(12) 0.0036(12) C21 0.0133(14) 0.0163(15) 0.0069(14) 0.0042(12) 0.0001(11) 0.0057(12) C22 0.0118(14) 0.0132(15) 0.0127(15) 0.0032(12) 0.0045(12) 0.0023(11) C23 0.0112(14) 0.0157(15) 0.0113(14) 0.0012(12) 0.0017(11) 0.0051(12) C24 0.0124(14) 0.0141(15) 0.0113(14) 0.0054(12) 0.0018(11) 0.0034(11) C25 0.0146(15) 0.0123(15) 0.0118(14) 0.0027(12) 0.0061(12) 0.0048(12) C26 0.0159(15) 0.0124(15) 0.0140(15) 0.0021(12) 0.0043(12) 0.0060(12) C27 0.0169(16) 0.0165(16) 0.0129(15) -0.0008(12) 0.0001(12) 0.0033(12) C28 0.0207(17) 0.0241(18) 0.0109(15) 0.0043(13) 0.0010(13) 0.0087(13) C29 0.0205(16) 0.0186(16) 0.0158(16) 0.0101(13) 0.0057(13) 0.0104(13) C30 0.0166(15) 0.0113(15) 0.0128(15) 0.0019(12) 0.0043(12) 0.0030(12) C31 0.0124(14) 0.0126(15) 0.0128(15) 0.0029(12) 0.0056(12) 0.0036(11) C32 0.0163(15) 0.0126(15) 0.0137(15) 0.0024(12) 0.0074(12) 0.0021(12) C33 0.036(2) 0.0173(18) 0.0189(18) -0.0015(14) -0.0018(15) -0.0050(15) C34 0.0142(15) 0.0102(15) 0.0139(15) -0.0004(12) 0.0046(12) 0.0042(11) C35 0.0178(15) 0.0118(15) 0.0149(15) 0.0025(12) 0.0038(12) 0.0045(12) C36 0.0130(14) 0.0122(15) 0.0148(15) 0.0042(12) 0.0024(12) 0.0011(11) C37 0.0150(15) 0.0128(15) 0.0197(16) 0.0044(13) 0.0040(13) 0.0033(12) C38 0.0152(15) 0.0097(15) 0.0235(17) 0.0069(13) -0.0020(13) 0.0022(12) C39 0.0123(15) 0.0171(16) 0.0224(17) 0.0115(13) -0.0015(13) -0.0011(12) C40 0.0137(15) 0.0164(16) 0.0164(16) 0.0058(13) 0.0025(12) 0.0020(12) C41 0.0088(14) 0.0116(14) 0.0130(15) 0.0033(12) -0.0010(11) 0.0003(11) C42 0.0124(14) 0.0162(15) 0.0077(14) 0.0009(12) 0.0014(11) 0.0038(12) 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' I I -0.4742 1.8119 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 O2 C12 115.4(2) C14 O3 C13 124.0(2) C32 O6 C33 114.6(3) C35 O7 C34 123.3(2) C2 C1 C10 108.4(3) C2 C1 C11 125.1(3) C10 C1 C11 126.5(3) C1 C2 C3 109.9(3) C1 C2 H2 125.1 C3 C2 H2 125.1 C2 C3 C4 108.1(3) C2 C3 C13 123.7(3) C4 C3 C13 128.0(3) C5 C4 C3 125.4(3) C5 C4 C10 127.4(3) C3 C4 C10 107.1(3) C6 C5 C4 129.1(3) C6 C5 H5 115.5 C4 C5 H5 115.5 C5 C6 C7 128.4(3) C5 C6 H6 115.8 C7 C6 H6 115.8 C8 C7 C6 129.4(3) C8 C7 H7 115.3 C6 C7 H7 115.3 C7 C8 C9 129.6(3) C7 C8 H8 115.2 C9 C8 H8 115.2 C10 C9 C8 128.5(3) C10 C9 H9 115.8 C8 C9 H9 115.8 C9 C10 C1 126.4(3) C9 C10 C4 127.2(3) C1 C10 C4 106.4(2) O1 C11 O2 122.8(3) O1 C11 C1 126.2(3) O2 C11 C1 111.0(2) O2 C12 H12A 109.5 O2 C12 H12B 109.5 H12A C12 H12B 109.5 O2 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C21 C13 O3 120.0(3) C21 C13 C3 130.2(3) O3 C13 C3 109.7(2) O4 C14 O3 117.1(3) O4 C14 C15 126.5(3) O3 C14 C15 116.4(3) C16 C15 C20 120.7(3) C16 C15 C14 118.4(3) C20 C15 C14 120.8(3) C17 C16 C15 119.7(3) C17 C16 H16 120.2 C15 C16 H16 120.2 C16 C17 C18 120.3(3) C16 C17 H17 119.8 C18 C17 H17 119.8 C19 C18 C17 120.3(3) C19 C18 H18 119.8 C17 C18 H18 119.8 C18 C19 C20 120.3(3) C18 C19 H19 119.8 C20 C19 H19 119.8 C19 C20 C15 118.6(3) C19 C20 C21 124.0(3) C15 C20 C21 117.3(3) C13 C21 C20 121.4(3) C13 C21 I1 119.4(2) C20 C21 I1 119.1(2) C23 C22 C31 108.3(3) C23 C22 C32 125.4(3) C31 C22 C32 126.3(3) C24 C23 C22 110.4(3) C24 C23 H23 124.8 C22 C23 H23 124.8 C23 C24 C25 108.0(3) C23 C24 C34 126.4(3) C25 C24 C34 125.5(3) C26 C25 C24 125.5(3) C26 C25 C31 127.6(3) C24 C25 C31 106.8(3) C25 C26 C27 128.8(3) C25 C26 H26 115.6 C27 C26 H26 115.6 C28 C27 C26 128.9(3) C28 C27 H27 115.6 C26 C27 H27 115.6 C27 C28 C29 129.3(3) C27 C28 H28 115.4 C29 C28 H28 115.4 C30 C29 C28 129.2(3) C30 C29 H29 115.4 C28 C29 H29 115.4 C29 C30 C31 128.6(3) C29 C30 H30 115.7 C31 C30 H30 115.7 C30 C31 C22 126.2(3) C30 C31 C25 127.4(3) C22 C31 C25 106.4(3) O5 C32 O6 122.7(3) O5 C32 C22 126.5(3) O6 C32 C22 110.7(3) O6 C33 H33A 109.5 O6 C33 H33B 109.5 H33A C33 H33B 109.5 O6 C33 H33C 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 C42 C34 O7 120.5(3) C42 C34 C24 130.0(3) O7 C34 C24 109.4(2) O8 C35 O7 117.0(3) O8 C35 C36 126.0(3) O7 C35 C36 117.0(3) C37 C36 C41 120.8(3) C37 C36 C35 118.7(3) C41 C36 C35 120.5(3) C38 C37 C36 120.4(3) C38 C37 H37 119.8 C36 C37 H37 119.8 C37 C38 C39 119.4(3) C37 C38 H38 120.3 C39 C38 H38 120.3 C40 C39 C38 121.0(3) C40 C39 H39 119.5 C38 C39 H39 119.5 C39 C40 C41 120.7(3) C39 C40 H40 119.7 C41 C40 H40 119.7 C40 C41 C36 117.7(3) C40 C41 C42 125.0(3) C36 C41 C42 117.3(3) C34 C42 C41 121.1(3) C34 C42 I2 118.9(2) C41 C42 I2 120.0(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance I1 C21 2.092(3) I2 C42 2.100(3) O1 C11 1.210(4) O2 C11 1.349(4) O2 C12 1.450(4) O3 C14 1.372(4) O3 C13 1.394(3) O4 C14 1.196(4) O5 C32 1.210(4) O6 C32 1.353(4) O6 C33 1.448(4) O7 C35 1.372(4) O7 C34 1.393(3) O8 C35 1.204(4) C1 C2 1.400(4) C1 C10 1.421(4) C1 C11 1.466(4) C2 C3 1.406(4) C2 H2 0.9500 C3 C4 1.411(4) C3 C13 1.456(4) C4 C5 1.393(4) C4 C10 1.479(4) C5 C6 1.392(4) C5 H5 0.9500 C6 C7 1.393(5) C6 H6 0.9500 C7 C8 1.379(5) C7 H7 0.9500 C8 C9 1.397(4) C8 H8 0.9500 C9 C10 1.388(4) C9 H9 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C21 1.344(4) C14 C15 1.474(4) C15 C16 1.393(4) C15 C20 1.406(4) C16 C17 1.381(5) C16 H16 0.9500 C17 C18 1.389(5) C17 H17 0.9500 C18 C19 1.389(4) C18 H18 0.9500 C19 C20 1.398(4) C19 H19 0.9500 C20 C21 1.463(4) C22 C23 1.398(4) C22 C31 1.413(4) C22 C32 1.466(4) C23 C24 1.388(4) C23 H23 0.9500 C24 C25 1.420(4) C24 C34 1.472(4) C25 C26 1.391(4) C25 C31 1.479(4) C26 C27 1.393(4) C26 H26 0.9500 C27 C28 1.388(4) C27 H27 0.9500 C28 C29 1.394(5) C28 H28 0.9500 C29 C30 1.391(4) C29 H29 0.9500 C30 C31 1.394(4) C30 H30 0.9500 C33 H33A 0.9800 C33 H33B 0.9800 C33 H33C 0.9800 C34 C42 1.341(4) C35 C36 1.460(4) C36 C37 1.391(4) C36 C41 1.416(4) C37 C38 1.376(4) C37 H37 0.9500 C38 C39 1.395(5) C38 H38 0.9500 C39 C40 1.380(4) C39 H39 0.9500 C40 C41 1.402(4) C40 H40 0.9500 C41 C42 1.461(4) 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 C10 C1 C2 C3 -1.1(3) C11 C1 C2 C3 177.1(3) C1 C2 C3 C4 3.2(3) C1 C2 C3 C13 178.9(3) C2 C3 C4 C5 171.5(3) C13 C3 C4 C5 -4.0(5) C2 C3 C4 C10 -3.9(3) C13 C3 C4 C10 -179.4(3) C3 C4 C5 C6 -178.9(3) C10 C4 C5 C6 -4.5(5) C4 C5 C6 C7 -3.1(6) C5 C6 C7 C8 3.6(6) C6 C7 C8 C9 2.0(6) C7 C8 C9 C10 -2.7(6) C8 C9 C10 C1 177.0(3) C8 C9 C10 C4 -4.1(5) C2 C1 C10 C9 177.7(3) C11 C1 C10 C9 -0.4(5) C2 C1 C10 C4 -1.3(3) C11 C1 C10 C4 -179.5(3) C5 C4 C10 C9 9.0(5) C3 C4 C10 C9 -175.8(3) C5 C4 C10 C1 -172.0(3) C3 C4 C10 C1 3.2(3) C12 O2 C11 O1 -2.1(4) C12 O2 C11 C1 178.7(2) C2 C1 C11 O1 -172.5(3) C10 C1 C11 O1 5.3(5) C2 C1 C11 O2 6.7(4) C10 C1 C11 O2 -175.4(3) C14 O3 C13 C21 2.0(4) C14 O3 C13 C3 179.6(2) C2 C3 C13 C21 126.9(4) C4 C3 C13 C21 -58.3(5) C2 C3 C13 O3 -50.3(4) C4 C3 C13 O3 124.5(3) C13 O3 C14 O4 179.7(3) C13 O3 C14 C15 0.1(4) O4 C14 C15 C16 -1.3(5) O3 C14 C15 C16 178.3(3) O4 C14 C15 C20 178.9(3) O3 C14 C15 C20 -1.5(4) C20 C15 C16 C17 0.0(5) C14 C15 C16 C17 -179.8(3) C15 C16 C17 C18 0.0(5) C16 C17 C18 C19 -0.2(5) C17 C18 C19 C20 0.3(5) C18 C19 C20 C15 -0.3(4) C18 C19 C20 C21 178.6(3) C16 C15 C20 C19 0.1(4) C14 C15 C20 C19 179.9(3) C16 C15 C20 C21 -178.8(3) C14 C15 C20 C21 1.0(4) O3 C13 C21 C20 -2.6(4) C3 C13 C21 C20 -179.6(3) O3 C13 C21 I1 173.6(2) C3 C13 C21 I1 -3.4(4) C19 C20 C21 C13 -177.8(3) C15 C20 C21 C13 1.1(4) C19 C20 C21 I1 6.1(4) C15 C20 C21 I1 -175.0(2) C31 C22 C23 C24 0.0(3) C32 C22 C23 C24 -179.8(3) C22 C23 C24 C25 -0.1(3) C22 C23 C24 C34 175.7(3) C23 C24 C25 C26 -177.1(3) C34 C24 C25 C26 6.9(5) C23 C24 C25 C31 0.2(3) C34 C24 C25 C31 -175.7(3) C24 C25 C26 C27 176.8(3) C31 C25 C26 C27 0.1(5) C25 C26 C27 C28 3.5(6) C26 C27 C28 C29 -0.8(6) C27 C28 C29 C30 -3.8(6) C28 C29 C30 C31 2.6(6) C29 C30 C31 C22 -179.0(3) C29 C30 C31 C25 2.7(5) C23 C22 C31 C30 -178.5(3) C32 C22 C31 C30 1.3(5) C23 C22 C31 C25 0.1(3) C32 C22 C31 C25 179.9(3) C26 C25 C31 C30 -4.4(5) C24 C25 C31 C30 178.4(3) C26 C25 C31 C22 177.1(3) C24 C25 C31 C22 -0.1(3) C33 O6 C32 O5 0.9(4) C33 O6 C32 C22 -179.7(3) C23 C22 C32 O5 -178.3(3) C31 C22 C32 O5 1.9(5) C23 C22 C32 O6 2.3(4) C31 C22 C32 O6 -177.5(3) C35 O7 C34 C42 -3.1(4) C35 O7 C34 C24 176.8(3) C23 C24 C34 C42 55.0(5) C25 C24 C34 C42 -129.8(4) C23 C24 C34 O7 -124.9(3) C25 C24 C34 O7 50.3(4) C34 O7 C35 O8 -174.7(3) C34 O7 C35 C36 6.0(4) O8 C35 C36 C37 -2.5(5) O7 C35 C36 C37 176.7(3) O8 C35 C36 C41 175.8(3) O7 C35 C36 C41 -5.0(4) C41 C36 C37 C38 1.0(5) C35 C36 C37 C38 179.3(3) C36 C37 C38 C39 -0.1(5) C37 C38 C39 C40 -0.6(5) C38 C39 C40 C41 0.5(5) C39 C40 C41 C36 0.3(4) C39 C40 C41 C42 179.7(3) C37 C36 C41 C40 -1.1(4) C35 C36 C41 C40 -179.4(3) C37 C36 C41 C42 179.5(3) C35 C36 C41 C42 1.2(4) O7 C34 C42 C41 -1.1(4) C24 C34 C42 C41 179.1(3) O7 C34 C42 I2 177.8(2) C24 C34 C42 I2 -2.0(5) C40 C41 C42 C34 -177.5(3) C36 C41 C42 C34 1.9(4) C40 C41 C42 I2 3.6(4) C36 C41 C42 I2 -177.0(2)