#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:56:54 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294490 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572073.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_1572073 loop_ _publ_author_name 'Wieprecht, Nele' 'Krummenacher, Ivo' 'Wüst, Leonie' 'Michel, Maximilian' 'Fuchs, Sonja' 'Nees, Samuel' 'Härterich, Marcel' 'Braunschweig, Holger' _publ_section_title ; The forgotten borole: synthesis, properties and reactivity of a 1-boraindene. ; _journal_issue 31 _journal_name_full 'Chemical science' _journal_page_first 12496 _journal_page_last 12501 _journal_paper_doi 10.1039/d4sc03817g _journal_volume 15 _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C31 H24 B N' _chemical_formula_sum 'C31 H24 B N' _chemical_formula_weight 421.32 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2023-04-13 _audit_creation_method 'CIF-fill 1.4a (K.Radacki, 2005-23)' _audit_update_record ; 2024-06-05 deposited with the CCDC. 2024-07-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.7320(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.62580(10) _cell_length_b 13.3900(2) _cell_length_c 12.53570(10) _cell_measurement_reflns_used 13763 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 73.9130 _cell_measurement_theta_min 3.5490 _cell_volume 2260.62(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector HPA _diffrn_detector_area_resol_mean 10.0 _diffrn_detector_type 'HyPix Arc150' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): -------------------------------------------------------------------------- 1 \w -95.00 -23.00 0.50 0.10 -- -59.96 139.00-166.00 144 2 \w -105.00 -23.00 0.50 0.10 -- -69.45 139.00-166.00 164 3 \w -108.00 -30.00 0.50 0.10 -- -76.35 139.00-166.00 156 4 \w -97.00 -32.00 0.50 0.10 -- -78.00 114.00 -28.68 130 5 \w -100.00 -23.00 0.50 0.10 -- -69.45 132.00 17.00 154 6 \w -91.00 -18.00 0.50 0.10 -- -59.96 132.00 17.00 146 7 \w -106.00 -71.00 0.50 0.10 -- -58.00 -51.00 -36.17 70 8 \w -124.00 -94.00 0.50 0.10 -- -79.50 -64.00 -15.38 60 9 \w -125.00 -94.00 0.50 0.10 -- -79.50-119.00 75.31 62 10 \w -127.00 -92.00 0.50 0.10 -- -79.50 -54.00 93.83 70 11 \w -99.00 -64.00 0.50 0.10 -- -50.00 -47.00 152.39 70 12 \w -98.00 -63.00 0.50 0.10 -- -50.00 -52.00 11.77 70 13 \w -99.00 -64.00 0.50 0.10 -- -50.00 -47.00 -81.05 70 14 \w 36.00 103.00 0.50 0.10 -- 82.28-132.00 -51.00 134 15 \w 36.00 108.00 0.50 0.10 -- 82.28-139.00 133.00 144 16 \w 39.00 107.00 0.50 0.10 -- 85.25-138.00 164.21 136 17 \w 29.00 107.00 0.50 0.10 -- 71.14-139.00 133.00 156 18 \w 81.00 107.00 0.50 0.10 -- 85.25-137.00 109.96 52 19 \w 51.00 99.00 0.50 0.10 -- 85.25-121.00 -33.59 96 20 \w 67.00 93.00 0.50 0.10 -- 85.25-102.00 18.42 52 21 \w 37.00 93.00 0.50 0.10 -- 82.28-112.00 -60.00 112 22 \w 49.00 75.00 0.50 0.10 -- 85.25 -98.00-141.74 52 23 \w 57.00 83.00 0.50 0.10 -- 85.25-119.00-148.67 52 24 \w 40.00 90.00 0.50 0.10 -- 82.28 -95.00 -30.00 100 25 \w 40.00 90.00 0.50 0.10 -- 82.28 -95.00 30.00 100 26 \w 40.00 90.00 0.50 0.10 -- 82.28 -95.00 60.00 100 27 \w 42.00 92.00 0.50 0.10 -- 85.25 -98.00 171.00 100 28 \w 106.00 131.00 0.50 0.10 -- 85.25 120.00 131.75 50 29 \w 100.00 131.00 0.50 0.10 -- 85.25 56.00 66.42 62 30 \w 101.00 126.00 0.50 0.10 -- 85.25 48.00 175.20 50 31 \w 46.00 133.00 0.50 0.10 -- 82.28 15.00 150.00 174 32 \w 46.00 133.00 0.50 0.10 -- 82.28 15.00 -90.00 174 33 \w 100.00 133.00 0.50 0.10 -- 85.25 46.00-137.07 66 34 \w 100.00 134.00 0.50 0.10 -- 85.25 45.00-163.63 68 35 \w 46.00 133.00 0.50 0.10 -- 82.28 15.00-180.00 174 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku XtaLAB Synergy-R' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type ; CrysAlisPro convention (1999,Acta A55,543-557) ; _diffrn_orient_matrix_UB_11 -0.0260560000 _diffrn_orient_matrix_UB_12 -0.1100496000 _diffrn_orient_matrix_UB_13 0.0183331000 _diffrn_orient_matrix_UB_21 -0.0777082000 _diffrn_orient_matrix_UB_22 0.0335282000 _diffrn_orient_matrix_UB_23 0.0699782000 _diffrn_orient_matrix_UB_31 -0.0797562000 _diffrn_orient_matrix_UB_32 0.0032271000 _diffrn_orient_matrix_UB_33 -0.1010947000 _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_xray_symbol K-L~2,3~ _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_unetI/netI 0.0163 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 16399 _diffrn_reflns_point_group_measured_fraction_full 0.801 _diffrn_reflns_point_group_measured_fraction_max 0.771 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.131 _diffrn_reflns_theta_min 4.657 _diffrn_source 'rotating-anode X-ray tube' _diffrn_source_type 'PhotonJet-R X-ray Source' _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.238 _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_preparation ; For data collection the crystal was immersed in a film of perfluoropolyether oil, mounted on a polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800). ; _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.123 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1247 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 3575 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0316 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.6109P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.0808 _reflns_Friedel_coverage 0.572 _reflns_Friedel_fraction_full 0.606 _reflns_Friedel_fraction_max 0.562 _reflns_number_gt 3517 _reflns_number_total 3575 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03817g2.cif _cod_data_source_block 1-Py _cod_depositor_comments 'Adding full bibliography for 1572071--1572079.cif.' _cod_original_sg_symbol_H-M 'C c' _cod_database_code 1572073 _shelx_shelxl_version_number 2018/3 _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 0.823 _shelx_estimated_absorpt_t_max 0.949 _shelx_res_file ; TITL MaMi153_NeWi_a.res in Cc MaMi153_NeWi_a.res created by SHELXL-2018/3 at 10:48:15 on 13-Apr-2023 REM Old TITL MaMi153_NeWi in C2/c REM SHELXT solution in Cc: R1 0.093, Rweak 0.040, Alpha 0.001 REM 0.964 for 99 systematic absences, Orientation as input REM Flack x = 0.435 ( 0.274 ) from 1251 Parsons' quotients REM Formula found by SHELXT: C31 B N CELL 1.54184 13.6258 13.3900 12.5357 90.000 98.732 90.000 ZERR 4.000 0.0001 0.0002 0.0001 0.000 0.001 0.000 LATT -7 SYMM X, -Y, 1/2+Z SFAC C H B N UNIT 124 96 4 4 TEMP -173 SIZE 0.10 0.16 0.38 L.S. 10 BOND $H LIST 4 ACTA CONF FMAP 2 PLAN 20 WGHT 0.049300 0.610900 FVAR 0.58546 N001 4 0.606893 0.767302 0.595147 11.00000 0.02355 0.02362 = 0.02480 0.00020 0.00558 0.00082 C002 1 0.524183 0.833083 0.405247 11.00000 0.01807 0.02769 = 0.02789 -0.00036 0.00654 0.00036 C003 1 0.445391 0.579065 0.472171 11.00000 0.02311 0.02626 = 0.02340 0.00032 0.00463 0.00010 C004 1 0.607166 0.585240 0.402753 11.00000 0.02479 0.02205 = 0.03266 0.00457 0.01088 0.00008 C005 1 0.596472 0.745019 0.697665 11.00000 0.02920 0.02796 = 0.02694 0.00078 0.00826 0.00367 AFIX 43 H005 2 0.533956 0.722038 0.712440 11.00000 -1.20000 AFIX 0 C006 1 0.424047 0.472503 0.444827 11.00000 0.02624 0.02815 = 0.02542 -0.00005 0.01041 -0.00397 C007 1 0.374396 0.643163 0.519939 11.00000 0.02208 0.02898 = 0.02252 0.00179 0.00448 0.00209 C008 1 0.542033 0.933284 0.433941 11.00000 0.02818 0.02905 = 0.02772 0.00047 0.00771 -0.00008 AFIX 43 H008 2 0.553923 0.950318 0.508352 11.00000 -1.20000 AFIX 0 C009 1 0.335783 0.444815 0.380423 11.00000 0.03109 0.03378 = 0.02795 -0.00080 0.00739 -0.00479 AFIX 43 H009 2 0.287405 0.494239 0.356479 11.00000 -1.20000 AFIX 0 C00A 1 0.352299 0.812333 0.575613 11.00000 0.02517 0.02885 = 0.02766 -0.00079 0.00509 0.00241 AFIX 43 H00A 2 0.375570 0.878985 0.586492 11.00000 -1.20000 AFIX 0 C00B 1 0.765151 0.787705 0.760961 11.00000 0.03073 0.03687 = 0.03485 -0.00816 -0.00175 0.00460 AFIX 43 H00B 2 0.819267 0.794826 0.817902 11.00000 -1.20000 AFIX 0 C00C 1 0.527486 0.631110 0.455596 11.00000 0.02241 0.02710 = 0.02439 0.00084 0.00485 0.00042 C00D 1 0.493343 0.397908 0.480075 11.00000 0.02866 0.02952 = 0.03459 0.00308 0.01106 -0.00058 AFIX 43 H00D 2 0.553709 0.415172 0.524632 11.00000 -1.20000 AFIX 0 C00E 1 0.506017 0.813168 0.294182 11.00000 0.02272 0.02956 = 0.02676 -0.00051 0.00460 0.00231 AFIX 43 H00E 2 0.494732 0.746104 0.270763 11.00000 -1.20000 AFIX 0 C00F 1 0.411308 0.741079 0.535522 11.00000 0.02378 0.02781 = 0.02271 0.00085 0.00543 0.00154 C00G 1 0.281870 0.615961 0.545736 11.00000 0.02352 0.03400 = 0.02805 0.00032 0.00726 -0.00259 AFIX 43 H00G 2 0.258566 0.549208 0.536209 11.00000 -1.20000 AFIX 0 C00H 1 0.696558 0.798878 0.575451 11.00000 0.02451 0.03364 = 0.03208 0.00161 0.00646 -0.00202 AFIX 43 H00H 2 0.704783 0.813769 0.503242 11.00000 -1.20000 AFIX 0 C00I 1 0.673676 0.754559 0.781583 11.00000 0.03705 0.03844 = 0.02491 -0.00218 0.00500 0.00671 AFIX 43 H00I 2 0.664250 0.738510 0.853149 11.00000 -1.20000 AFIX 0 C00J 1 0.543072 1.008645 0.358256 11.00000 0.03214 0.02650 = 0.03646 0.00236 0.01054 -0.00074 AFIX 43 H00J 2 0.557371 1.075394 0.381203 11.00000 -1.20000 AFIX 0 C00K 1 0.503940 0.888165 0.217098 11.00000 0.02649 0.04001 = 0.02522 0.00279 0.00755 0.00527 AFIX 43 H00K 2 0.489317 0.872073 0.142568 11.00000 -1.20000 AFIX 0 C00L 1 0.523171 0.986443 0.248760 11.00000 0.03056 0.03467 = 0.03251 0.01034 0.01229 0.00577 AFIX 43 H00L 2 0.522742 1.037783 0.196386 11.00000 -1.20000 AFIX 0 C00M 1 0.776191 0.810271 0.655678 11.00000 0.02593 0.03962 = 0.03650 -0.00146 0.00209 -0.00195 AFIX 43 H00M 2 0.838102 0.833341 0.639217 11.00000 -1.20000 AFIX 0 C00N 1 0.224503 0.689299 0.585860 11.00000 0.02273 0.04366 = 0.03006 0.00121 0.01014 -0.00013 AFIX 43 H00N 2 0.161242 0.672325 0.603618 11.00000 -1.20000 AFIX 0 C00O 1 0.317634 0.345393 0.350703 11.00000 0.03952 0.04145 = 0.03173 -0.00773 0.01278 -0.01476 AFIX 43 H00O 2 0.257102 0.327497 0.306825 11.00000 -1.20000 AFIX 0 C00P 1 0.585223 0.547016 0.298259 11.00000 0.03612 0.02659 = 0.03294 0.00143 0.01395 0.00320 AFIX 43 H00P 2 0.519447 0.552017 0.260557 11.00000 -1.20000 AFIX 0 C00Q 1 0.704549 0.577243 0.455815 11.00000 0.02504 0.02590 = 0.04411 0.00521 0.01092 -0.00019 AFIX 43 H00Q 2 0.721500 0.603881 0.526449 11.00000 -1.20000 AFIX 0 C00R 1 0.387660 0.272622 0.385000 11.00000 0.04953 0.02934 = 0.04183 -0.00720 0.02367 -0.01114 AFIX 43 H00R 2 0.375807 0.205113 0.363522 11.00000 -1.20000 AFIX 0 C00S 1 0.258575 0.786243 0.600065 11.00000 0.02668 0.04093 = 0.02884 -0.00001 0.00782 0.00791 AFIX 43 H00S 2 0.218283 0.835528 0.626552 11.00000 -1.20000 AFIX 0 C00T 1 0.754559 0.493390 0.302772 11.00000 0.04487 0.02695 = 0.06933 0.00768 0.03822 0.00666 AFIX 43 H00T 2 0.804574 0.462380 0.269088 11.00000 -1.20000 AFIX 0 C00U 1 0.474785 0.298590 0.450544 11.00000 0.04182 0.02767 = 0.04584 0.00334 0.02110 -0.00015 AFIX 43 H00U 2 0.522180 0.248567 0.475550 11.00000 -1.20000 AFIX 0 C00V 1 0.777175 0.530631 0.406351 11.00000 0.02872 0.02977 = 0.06542 0.01073 0.02041 0.00356 AFIX 43 H00V 2 0.842802 0.524398 0.444154 11.00000 -1.20000 AFIX 0 C00W 1 0.658534 0.501519 0.248298 11.00000 0.05251 0.02737 = 0.04511 0.00097 0.02917 0.00337 AFIX 43 H00W 2 0.642545 0.476164 0.176997 11.00000 -1.20000 AFIX 0 B00X 3 0.519106 0.747135 0.494918 11.00000 0.02010 0.02853 = 0.02526 -0.00054 0.00640 -0.00104 HKLF 4 REM MaMi153_NeWi_a.res in Cc REM wR2 = 0.080832, GooF = S = 1.07629, Restrained GooF = 1.07596 for all data REM R1 = 0.031575 for 3517 Fo > 4sig(Fo) and 0.031948 for all 3575 data REM 298 parameters refined using 2 restraints END WGHT 0.0493 0.6108 REM Highest difference peak 0.123, deepest hole -0.232, 1-sigma level 0.040 Q1 1 0.4373 0.5225 0.4594 11.00000 0.05 0.12 Q2 1 0.6418 0.9418 0.5896 11.00000 0.05 0.11 Q3 1 0.5451 0.7855 0.4441 11.00000 0.05 0.11 Q4 1 0.6856 0.6429 0.6149 11.00000 0.05 0.11 Q5 1 0.8645 0.8927 0.8388 11.00000 0.05 0.11 Q6 1 0.4607 0.4371 0.4670 11.00000 0.05 0.11 Q7 1 0.6827 0.6287 0.8923 11.00000 0.05 0.11 Q8 1 0.5767 1.1641 0.3636 11.00000 0.05 0.10 Q9 1 0.4835 0.6009 0.2390 11.00000 0.05 0.10 Q10 1 0.5537 0.4984 0.5990 11.00000 0.05 0.10 Q11 1 0.4687 0.6403 0.2984 11.00000 0.05 0.10 Q12 1 0.8637 0.6046 0.5584 11.00000 0.05 0.10 Q13 1 0.7348 0.6294 0.5864 11.00000 0.05 0.10 Q14 1 0.3973 0.1836 0.3973 11.00000 0.05 0.10 Q15 1 0.4964 1.0882 0.4034 11.00000 0.05 0.10 Q16 1 0.1177 0.8726 0.6478 11.00000 0.05 0.10 Q17 1 0.6199 1.0931 0.1821 11.00000 0.05 0.10 Q18 1 0.5561 0.4277 0.5631 11.00000 0.05 0.10 Q19 1 0.6531 0.4044 0.1175 11.00000 0.05 0.10 Q20 1 0.2984 0.5014 0.3269 11.00000 0.05 0.10 ; _shelx_res_checksum 13749 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N001 N 0.60689(12) 0.76730(12) 0.59515(14) 0.0238(3) Uani 1 1 d . . . . . C002 C 0.52418(13) 0.83308(14) 0.40525(16) 0.0242(4) Uani 1 1 d . . . . . C003 C 0.44539(14) 0.57906(14) 0.47217(16) 0.0241(4) Uani 1 1 d . . . . . C004 C 0.60717(14) 0.58524(14) 0.40275(17) 0.0258(4) Uani 1 1 d . . . . . C005 C 0.59647(16) 0.74502(15) 0.69766(18) 0.0276(4) Uani 1 1 d . . . . . H005 H 0.533956 0.722038 0.712440 0.033 Uiso 1 1 calc R U . . . C006 C 0.42405(15) 0.47250(15) 0.44483(16) 0.0259(4) Uani 1 1 d . . . . . C007 C 0.37440(14) 0.64316(15) 0.51994(16) 0.0244(4) Uani 1 1 d . . . . . C008 C 0.54203(15) 0.93328(15) 0.43394(17) 0.0280(4) Uani 1 1 d . . . . . H008 H 0.553923 0.950318 0.508352 0.034 Uiso 1 1 calc R U . . . C009 C 0.33578(16) 0.44482(16) 0.38042(17) 0.0306(4) Uani 1 1 d . . . . . H009 H 0.287405 0.494239 0.356479 0.037 Uiso 1 1 calc R U . . . C00A C 0.35230(15) 0.81233(15) 0.57561(17) 0.0271(4) Uani 1 1 d . . . . . H00A H 0.375570 0.878985 0.586492 0.033 Uiso 1 1 calc R U . . . C00B C 0.76515(17) 0.78770(17) 0.76096(19) 0.0348(5) Uani 1 1 d . . . . . H00B H 0.819267 0.794826 0.817902 0.042 Uiso 1 1 calc R U . . . C00C C 0.52749(14) 0.63111(15) 0.45560(16) 0.0245(4) Uani 1 1 d . . . . . C00D C 0.49334(16) 0.39791(16) 0.48007(18) 0.0303(5) Uani 1 1 d . . . . . H00D H 0.553709 0.415172 0.524632 0.036 Uiso 1 1 calc R U . . . C00E C 0.50602(14) 0.81317(15) 0.29418(16) 0.0263(4) Uani 1 1 d . . . . . H00E H 0.494732 0.746104 0.270763 0.032 Uiso 1 1 calc R U . . . C00F C 0.41131(14) 0.74108(14) 0.53552(16) 0.0246(4) Uani 1 1 d . . . . . C00G C 0.28187(15) 0.61596(16) 0.54574(17) 0.0282(4) Uani 1 1 d . . . . . H00G H 0.258566 0.549208 0.536209 0.034 Uiso 1 1 calc R U . . . C00H C 0.69656(15) 0.79888(16) 0.57545(18) 0.0299(4) Uani 1 1 d . . . . . H00H H 0.704783 0.813769 0.503242 0.036 Uiso 1 1 calc R U . . . C00I C 0.67368(18) 0.75456(17) 0.78158(18) 0.0334(5) Uani 1 1 d . . . . . H00I H 0.664250 0.738510 0.853149 0.040 Uiso 1 1 calc R U . . . C00J C 0.54307(16) 1.00865(15) 0.35826(18) 0.0311(5) Uani 1 1 d . . . . . H00J H 0.557371 1.075394 0.381203 0.037 Uiso 1 1 calc R U . . . C00K C 0.50394(15) 0.88816(17) 0.21710(18) 0.0302(4) Uani 1 1 d . . . . . H00K H 0.489317 0.872073 0.142568 0.036 Uiso 1 1 calc R U . . . C00L C 0.52317(16) 0.98644(16) 0.24876(18) 0.0318(5) Uani 1 1 d . . . . . H00L H 0.522742 1.037783 0.196386 0.038 Uiso 1 1 calc R U . . . C00M C 0.77619(16) 0.81027(17) 0.65568(19) 0.0343(5) Uani 1 1 d . . . . . H00M H 0.838102 0.833341 0.639217 0.041 Uiso 1 1 calc R U . . . C00N C 0.22450(15) 0.68930(17) 0.58586(18) 0.0315(5) Uani 1 1 d . . . . . H00N H 0.161242 0.672325 0.603618 0.038 Uiso 1 1 calc R U . . . C00O C 0.31763(18) 0.34539(17) 0.35070(19) 0.0368(5) Uani 1 1 d . . . . . H00O H 0.257102 0.327497 0.306825 0.044 Uiso 1 1 calc R U . . . C00P C 0.58522(17) 0.54702(15) 0.29826(18) 0.0310(5) Uani 1 1 d . . . . . H00P H 0.519447 0.552017 0.260557 0.037 Uiso 1 1 calc R U . . . C00Q C 0.70455(15) 0.57724(15) 0.45581(19) 0.0311(5) Uani 1 1 d . . . . . H00Q H 0.721500 0.603881 0.526449 0.037 Uiso 1 1 calc R U . . . C00R C 0.38766(19) 0.27262(17) 0.3850(2) 0.0385(5) Uani 1 1 d . . . . . H00R H 0.375807 0.205113 0.363522 0.046 Uiso 1 1 calc R U . . . C00S C 0.25857(16) 0.78624(17) 0.60006(17) 0.0318(5) Uani 1 1 d . . . . . H00S H 0.218283 0.835528 0.626552 0.038 Uiso 1 1 calc R U . . . C00T C 0.75456(19) 0.49339(16) 0.3028(2) 0.0440(7) Uani 1 1 d . . . . . H00T H 0.804574 0.462380 0.269088 0.053 Uiso 1 1 calc R U . . . C00U C 0.47478(18) 0.29859(16) 0.4505(2) 0.0369(5) Uani 1 1 d . . . . . H00U H 0.522180 0.248567 0.475550 0.044 Uiso 1 1 calc R U . . . C00V C 0.77718(17) 0.53063(16) 0.4064(2) 0.0399(6) Uani 1 1 d . . . . . H00V H 0.842802 0.524398 0.444154 0.048 Uiso 1 1 calc R U . . . C00W C 0.6585(2) 0.50152(16) 0.2483(2) 0.0394(6) Uani 1 1 d . . . . . H00W H 0.642545 0.476164 0.176997 0.047 Uiso 1 1 calc R U . . . B00X B 0.51911(16) 0.74713(17) 0.49492(19) 0.0243(4) 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 N001 0.0235(8) 0.0236(7) 0.0248(8) 0.0002(6) 0.0056(7) 0.0008(6) C002 0.0181(8) 0.0277(9) 0.0279(10) -0.0004(8) 0.0065(8) 0.0004(7) C003 0.0231(9) 0.0263(9) 0.0234(9) 0.0003(7) 0.0046(8) 0.0001(7) C004 0.0248(9) 0.0220(9) 0.0327(11) 0.0046(8) 0.0109(8) 0.0001(7) C005 0.0292(11) 0.0280(9) 0.0269(10) 0.0008(8) 0.0083(9) 0.0037(8) C006 0.0262(9) 0.0282(10) 0.0254(10) 0.0000(8) 0.0104(8) -0.0040(8) C007 0.0221(9) 0.0290(10) 0.0225(9) 0.0018(7) 0.0045(7) 0.0021(7) C008 0.0282(10) 0.0290(10) 0.0277(10) 0.0005(8) 0.0077(8) -0.0001(8) C009 0.0311(10) 0.0338(10) 0.0279(11) -0.0008(9) 0.0074(9) -0.0048(8) C00A 0.0252(10) 0.0288(10) 0.0277(11) -0.0008(8) 0.0051(8) 0.0024(8) C00B 0.0307(11) 0.0369(11) 0.0348(13) -0.0082(10) -0.0018(9) 0.0046(9) C00C 0.0224(9) 0.0271(9) 0.0244(10) 0.0008(8) 0.0049(8) 0.0004(7) C00D 0.0287(10) 0.0295(10) 0.0346(11) 0.0031(9) 0.0111(9) -0.0006(8) C00E 0.0227(9) 0.0296(10) 0.0268(10) -0.0005(8) 0.0046(8) 0.0023(8) C00F 0.0238(10) 0.0278(9) 0.0227(10) 0.0008(8) 0.0054(8) 0.0015(7) C00G 0.0235(10) 0.0340(10) 0.0281(11) 0.0003(8) 0.0073(8) -0.0026(8) C00H 0.0245(10) 0.0336(11) 0.0321(11) 0.0016(9) 0.0065(8) -0.0020(8) C00I 0.0371(11) 0.0384(11) 0.0249(11) -0.0022(9) 0.0050(9) 0.0067(9) C00J 0.0321(11) 0.0265(10) 0.0365(12) 0.0024(9) 0.0105(9) -0.0007(8) C00K 0.0265(10) 0.0400(11) 0.0252(10) 0.0028(9) 0.0076(8) 0.0053(8) C00L 0.0306(11) 0.0347(11) 0.0325(11) 0.0103(9) 0.0123(9) 0.0058(9) C00M 0.0259(10) 0.0396(12) 0.0365(13) -0.0015(9) 0.0021(9) -0.0019(8) C00N 0.0227(9) 0.0437(12) 0.0301(11) 0.0012(9) 0.0101(8) -0.0001(9) C00O 0.0395(12) 0.0415(12) 0.0317(11) -0.0077(10) 0.0128(9) -0.0148(10) C00P 0.0361(11) 0.0266(9) 0.0329(12) 0.0014(8) 0.0140(9) 0.0032(8) C00Q 0.0250(10) 0.0259(10) 0.0441(13) 0.0052(9) 0.0109(9) -0.0002(8) C00R 0.0495(14) 0.0293(11) 0.0418(13) -0.0072(9) 0.0237(11) -0.0111(10) C00S 0.0267(10) 0.0409(11) 0.0288(11) 0.0000(9) 0.0078(8) 0.0079(9) C00T 0.0449(13) 0.0269(10) 0.0693(18) 0.0077(11) 0.0382(14) 0.0067(10) C00U 0.0418(13) 0.0277(10) 0.0458(13) 0.0033(10) 0.0211(11) -0.0001(9) C00V 0.0287(11) 0.0298(10) 0.0654(17) 0.0107(11) 0.0204(11) 0.0036(9) C00W 0.0525(14) 0.0274(10) 0.0451(14) 0.0010(10) 0.0292(12) 0.0034(9) B00X 0.0201(10) 0.0285(10) 0.0253(11) -0.0005(9) 0.0064(9) -0.0010(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 1 -2 0.0917 -1 -1 1 0.0527 0 -1 0 0.0413 1 -2 -1 0.0616 -1 2 1 0.0426 -1 0 1 0.0520 1 0 -1 0.0991 2 1 1 0.1871 -1 1 -2 0.1565 -2 -1 -1 0.1510 1 2 2 0.1545 2 -1 2 0.1860 0 2 -1 0.0833 1 2 0 0.1111 0 0 1 0.1277 0 -1 2 0.1151 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 C005 N001 C00H 118.22(18) . . ? C005 N001 B00X 122.02(16) . . ? C00H N001 B00X 119.48(16) . . ? C008 C002 C00E 115.77(18) . . ? C008 C002 B00X 121.81(18) . . ? C00E C002 B00X 122.34(17) . . ? C00C C003 C007 111.50(16) . . ? C00C C003 C006 126.40(17) . . ? C007 C003 C006 122.08(16) . . ? C00Q C004 C00P 118.16(18) . . ? C00Q C004 C00C 121.66(19) . . ? C00P C004 C00C 120.16(18) . . ? N001 C005 C00I 121.97(18) . . ? N001 C005 H005 119.0 . . ? C00I C005 H005 119.0 . . ? C009 C006 C00D 118.35(19) . . ? C009 C006 C003 120.71(19) . . ? C00D C006 C003 120.90(19) . . ? C00G C007 C00F 121.80(18) . . ? C00G C007 C003 127.49(18) . . ? C00F C007 C003 110.69(16) . . ? C00J C008 C002 122.74(19) . . ? C00J C008 H008 118.6 . . ? C002 C008 H008 118.6 . . ? C006 C009 C00O 120.8(2) . . ? C006 C009 H009 119.6 . . ? C00O C009 H009 119.6 . . ? C00F C00A C00S 120.27(19) . . ? C00F C00A H00A 119.9 . . ? C00S C00A H00A 119.9 . . ? C00I C00B C00M 118.6(2) . . ? C00I C00B H00B 120.7 . . ? C00M C00B H00B 120.7 . . ? C003 C00C C004 121.95(17) . . ? C003 C00C B00X 110.07(16) . . ? C004 C00C B00X 127.89(16) . . ? C00U C00D C006 120.7(2) . . ? C00U C00D H00D 119.6 . . ? C006 C00D H00D 119.6 . . ? C00K C00E C002 122.30(19) . . ? C00K C00E H00E 118.8 . . ? C002 C00E H00E 118.8 . . ? C00A C00F C007 118.39(17) . . ? C00A C00F B00X 132.67(18) . . ? C007 C00F B00X 108.87(16) . . ? C00N C00G C007 118.34(19) . . ? C00N C00G H00G 120.8 . . ? C007 C00G H00G 120.8 . . ? N001 C00H C00M 122.5(2) . . ? N001 C00H H00H 118.7 . . ? C00M C00H H00H 118.7 . . ? C005 C00I C00B 119.5(2) . . ? C005 C00I H00I 120.2 . . ? C00B C00I H00I 120.2 . . ? C008 C00J C00L 119.9(2) . . ? C008 C00J H00J 120.0 . . ? C00L C00J H00J 120.0 . . ? C00L C00K C00E 120.2(2) . . ? C00L C00K H00K 119.9 . . ? C00E C00K H00K 119.9 . . ? C00K C00L C00J 119.02(19) . . ? C00K C00L H00L 120.5 . . ? C00J C00L H00L 120.5 . . ? C00H C00M C00B 119.1(2) . . ? C00H C00M H00M 120.4 . . ? C00B C00M H00M 120.4 . . ? C00S C00N C00G 120.81(18) . . ? C00S C00N H00N 119.6 . . ? C00G C00N H00N 119.6 . . ? C00R C00O C009 120.2(2) . . ? C00R C00O H00O 119.9 . . ? C009 C00O H00O 119.9 . . ? C004 C00P C00W 121.0(2) . . ? C004 C00P H00P 119.5 . . ? C00W C00P H00P 119.5 . . ? C00V C00Q C004 120.7(2) . . ? C00V C00Q H00Q 119.6 . . ? C004 C00Q H00Q 119.6 . . ? C00U C00R C00O 119.8(2) . . ? C00U C00R H00R 120.1 . . ? C00O C00R H00R 120.1 . . ? C00N C00S C00A 120.37(18) . . ? C00N C00S H00S 119.8 . . ? C00A C00S H00S 119.8 . . ? C00V C00T C00W 119.6(2) . . ? C00V C00T H00T 120.2 . . ? C00W C00T H00T 120.2 . . ? C00R C00U C00D 120.2(2) . . ? C00R C00U H00U 119.9 . . ? C00D C00U H00U 119.9 . . ? C00T C00V C00Q 120.5(2) . . ? C00T C00V H00V 119.7 . . ? C00Q C00V H00V 119.7 . . ? C00T C00W C00P 120.0(2) . . ? C00T C00W H00W 120.0 . . ? C00P C00W H00W 120.0 . . ? C002 B00X N001 108.41(15) . . ? C002 B00X C00F 112.86(16) . . ? N001 B00X C00F 111.14(16) . . ? C002 B00X C00C 116.94(17) . . ? N001 B00X C00C 108.31(16) . . ? C00F B00X C00C 98.87(15) . . ? 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 N001 C005 1.348(3) . ? N001 C00H 1.351(2) . ? N001 B00X 1.621(3) . ? C002 C008 1.401(3) . ? C002 C00E 1.402(3) . ? C002 B00X 1.618(3) . ? C003 C00C 1.360(3) . ? C003 C007 1.486(2) . ? C003 C006 1.486(3) . ? C004 C00Q 1.395(3) . ? C004 C00P 1.396(3) . ? C004 C00C 1.488(3) . ? C005 C00I 1.376(3) . ? C005 H005 0.9500 . ? C006 C009 1.393(3) . ? C006 C00D 1.399(3) . ? C007 C00G 1.397(3) . ? C007 C00F 1.407(3) . ? C008 C00J 1.387(3) . ? C008 H008 0.9500 . ? C009 C00O 1.394(3) . ? C009 H009 0.9500 . ? C00A C00F 1.390(3) . ? C00A C00S 1.402(3) . ? C00A H00A 0.9500 . ? C00B C00I 1.384(3) . ? C00B C00M 1.384(3) . ? C00B H00B 0.9500 . ? C00C B00X 1.639(3) . ? C00D C00U 1.393(3) . ? C00D H00D 0.9500 . ? C00E C00K 1.391(3) . ? C00E H00E 0.9500 . ? C00F B00X 1.628(3) . ? C00G C00N 1.396(3) . ? C00G H00G 0.9500 . ? C00H C00M 1.371(3) . ? C00H H00H 0.9500 . ? C00I H00I 0.9500 . ? C00J C00L 1.390(3) . ? C00J H00J 0.9500 . ? C00K C00L 1.388(3) . ? C00K H00K 0.9500 . ? C00L H00L 0.9500 . ? C00M H00M 0.9500 . ? C00N C00S 1.381(3) . ? C00N H00N 0.9500 . ? C00O C00R 1.386(4) . ? C00O H00O 0.9500 . ? C00P C00W 1.397(3) . ? C00P H00P 0.9500 . ? C00Q C00V 1.393(3) . ? C00Q H00Q 0.9500 . ? C00R C00U 1.382(4) . ? C00R H00R 0.9500 . ? C00S H00S 0.9500 . ? C00T C00V 1.381(4) . ? C00T C00W 1.385(4) . ? C00T H00T 0.9500 . ? C00U H00U 0.9500 . ? C00V H00V 0.9500 . ? C00W H00W 0.9500 . ? 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 C00H N001 C005 C00I 0.7(3) . . . . ? B00X N001 C005 C00I 174.62(19) . . . . ? C00C C003 C006 C009 -125.5(2) . . . . ? C007 C003 C006 C009 52.7(3) . . . . ? C00C C003 C006 C00D 52.3(3) . . . . ? C007 C003 C006 C00D -129.4(2) . . . . ? C00C C003 C007 C00G 178.6(2) . . . . ? C006 C003 C007 C00G 0.1(3) . . . . ? C00C C003 C007 C00F -0.1(2) . . . . ? C006 C003 C007 C00F -178.55(18) . . . . ? C00E C002 C008 C00J -0.7(3) . . . . ? B00X C002 C008 C00J -177.57(18) . . . . ? C00D C006 C009 C00O -0.8(3) . . . . ? C003 C006 C009 C00O 177.09(19) . . . . ? C007 C003 C00C C004 -176.47(18) . . . . ? C006 C003 C00C C004 1.9(3) . . . . ? C007 C003 C00C B00X 0.2(2) . . . . ? C006 C003 C00C B00X 178.56(19) . . . . ? C00Q C004 C00C C003 -119.4(2) . . . . ? C00P C004 C00C C003 59.3(3) . . . . ? C00Q C004 C00C B00X 64.6(3) . . . . ? C00P C004 C00C B00X -116.7(2) . . . . ? C009 C006 C00D C00U 0.6(3) . . . . ? C003 C006 C00D C00U -177.33(18) . . . . ? C008 C002 C00E C00K -1.2(3) . . . . ? B00X C002 C00E C00K 175.66(17) . . . . ? C00S C00A C00F C007 0.3(3) . . . . ? C00S C00A C00F B00X 177.0(2) . . . . ? C00G C007 C00F C00A -1.4(3) . . . . ? C003 C007 C00F C00A 177.40(18) . . . . ? C00G C007 C00F B00X -178.81(19) . . . . ? C003 C007 C00F B00X 0.0(2) . . . . ? C00F C007 C00G C00N 1.4(3) . . . . ? C003 C007 C00G C00N -177.2(2) . . . . ? C005 N001 C00H C00M -0.9(3) . . . . ? B00X N001 C00H C00M -175.04(19) . . . . ? N001 C005 C00I C00B -0.2(3) . . . . ? C00M C00B C00I C005 -0.1(3) . . . . ? C002 C008 C00J C00L 1.8(3) . . . . ? C002 C00E C00K C00L 2.0(3) . . . . ? C00E C00K C00L C00J -0.9(3) . . . . ? C008 C00J C00L C00K -1.0(3) . . . . ? N001 C00H C00M C00B 0.7(3) . . . . ? C00I C00B C00M C00H -0.2(3) . . . . ? C007 C00G C00N C00S -0.2(3) . . . . ? C006 C009 C00O C00R -0.1(3) . . . . ? C00Q C004 C00P C00W 0.3(3) . . . . ? C00C C004 C00P C00W -178.45(19) . . . . ? C00P C004 C00Q C00V -1.2(3) . . . . ? C00C C004 C00Q C00V 177.55(18) . . . . ? C009 C00O C00R C00U 1.3(3) . . . . ? C00G C00N C00S C00A -0.8(3) . . . . ? C00F C00A C00S C00N 0.8(3) . . . . ? C00O C00R C00U C00D -1.5(3) . . . . ? C006 C00D C00U C00R 0.6(3) . . . . ? C00W C00T C00V C00Q -0.8(3) . . . . ? C004 C00Q C00V C00T 1.4(3) . . . . ? C00V C00T C00W C00P -0.1(3) . . . . ? C004 C00P C00W C00T 0.3(3) . . . . ? C008 C002 B00X N001 -41.5(2) . . . . ? C00E C002 B00X N001 141.90(17) . . . . ? C008 C002 B00X C00F 82.1(2) . . . . ? C00E C002 B00X C00F -94.5(2) . . . . ? C008 C002 B00X C00C -164.20(17) . . . . ? C00E C002 B00X C00C 19.2(3) . . . . ? C005 N001 B00X C002 146.99(16) . . . . ? C00H N001 B00X C002 -39.1(2) . . . . ? C005 N001 B00X C00F 22.4(2) . . . . ? C00H N001 B00X C00F -163.74(17) . . . . ? C005 N001 B00X C00C -85.2(2) . . . . ? C00H N001 B00X C00C 88.7(2) . . . . ? C00A C00F B00X C002 -52.5(3) . . . . ? C007 C00F B00X C002 124.42(19) . . . . ? C00A C00F B00X N001 69.5(3) . . . . ? C007 C00F B00X N001 -113.53(18) . . . . ? C00A C00F B00X C00C -176.8(2) . . . . ? C007 C00F B00X C00C 0.1(2) . . . . ? C003 C00C B00X C002 -121.54(19) . . . . ? C004 C00C B00X C002 54.9(3) . . . . ? C003 C00C B00X N001 115.68(18) . . . . ? C004 C00C B00X N001 -67.9(2) . . . . ? C003 C00C B00X C00F -0.2(2) . . . . ? C004 C00C B00X C00F 176.21(19) . . . . ?