#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:56:54 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294490 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572072.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_1572072 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_formula_moiety 'C35 H30 B N' _chemical_formula_sum 'C35 H30 B N' _chemical_formula_weight 475.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method 'CIF-fill 1.2y (K.Radacki, 2005-22)' _audit_update_record ; 2024-06-05 deposited with the CCDC. 2024-07-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 113.055(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2512(2) _cell_length_b 14.86320(10) _cell_length_c 14.8307(2) _cell_measurement_reflns_used 22096 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 73.4760 _cell_measurement_theta_min 3.6040 _cell_volume 2687.68(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.73a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.73a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.73a (Rigaku OD, 2020)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector HPA _diffrn_detector_area_resol_mean 10.0 _diffrn_detector_type 'HyPix Arc150' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -103.00 -68.00 0.50 5.77 -- -54.00 -50.00 172.94 70 2 \w -103.00 -68.00 0.50 5.77 -- -54.00 -48.00-135.67 70 3 \w -107.00 -72.00 0.50 5.77 -- -58.00 -49.00 -93.01 70 4 \w 16.00 66.00 0.50 5.77 -- 58.61 -95.00 60.00 100 5 \w -111.00 -76.00 0.50 5.77 -- -62.00 -50.00 77.96 70 6 \w -117.00 -83.00 0.50 5.77 -- -70.00 -55.00 16.16 68 7 \w -124.00 -87.00 0.50 5.77 -- -74.00 -44.00 -52.61 74 8 \w -125.00 -91.00 0.50 5.77 -- -79.50 -61.00 178.56 68 9 \w -124.00 -94.00 0.50 5.77 -- -79.50 -64.00 155.14 60 10 \w -105.00 -33.00 0.50 5.77 -- -79.50 135.00 36.34 144 11 \w -126.00 -92.00 0.50 5.77 -- -79.50 -57.00-128.87 68 12 \w -128.00 -95.00 0.50 5.77 -- -79.50-117.00 132.94 66 13 \w 46.00 133.00 0.50 5.77 -- 82.31 15.00-150.00 174 14 \w 46.00 133.00 0.50 5.77 -- 82.31 15.00 30.00 174 15 \w 34.00 97.00 0.50 5.77 -- 82.31-112.00-150.00 126 16 \w 40.00 90.00 0.50 5.77 -- 82.31 -95.00 -30.00 100 17 \w 40.00 90.00 0.50 5.77 -- 82.31 -95.00 30.00 100 18 \w 34.00 97.00 0.50 5.77 -- 82.31-112.00 30.00 126 19 \w 34.00 97.00 0.50 5.77 -- 82.31-112.00 60.00 126 20 \w 34.00 97.00 0.50 5.77 -- 82.31-112.00 150.00 126 21 \w 38.00 105.00 0.50 5.77 -- 85.25-134.00 145.81 134 22 \w 44.00 72.00 0.50 5.77 -- 85.25 -73.00-159.00 56 23 \w 39.00 107.00 0.50 5.77 -- 85.25-138.00 -99.18 136 24 \w 42.00 93.00 0.50 5.77 -- 85.25 -97.00 56.06 102 25 \w 39.00 95.00 0.50 5.77 -- 85.25-108.00 -71.71 112 26 \w 41.00 94.00 0.50 5.77 -- 85.25-100.00 5.58 106 27 \w 45.00 88.00 0.50 5.77 -- 85.25 -88.00-147.03 86 28 \w 44.00 90.00 0.50 5.77 -- 85.25 -91.00-113.07 92 29 \w 37.00 100.00 0.50 5.77 -- 85.25-122.00 176.20 126 30 \w 97.00 131.00 0.50 5.77 -- 85.25 60.00 74.43 68 31 \w 45.00 77.00 0.50 5.77 -- 85.25 -76.00 -70.20 64 32 \w 97.00 134.00 0.50 5.77 -- 85.25 125.00-114.18 74 33 \w 36.00 99.00 0.50 5.77 -- 85.25-121.00 -46.53 126 34 \w 101.00 130.00 0.50 5.77 -- 85.25 65.00 15.09 58 35 \w 99.00 134.00 0.50 5.77 -- 85.25 49.00 156.44 70 36 \w 30.00 60.00 0.50 5.77 -- 18.00 59.00 127.21 60 37 \w -74.00 -39.00 0.50 5.77 -- -26.00 -51.00 -87.24 70 38 \w -107.00 -72.00 0.50 5.77 -- -58.00 -49.00 37.35 70 39 \w -120.00 -82.00 0.50 5.77 -- -70.00 -42.00-104.34 76 40 \w -121.00 -86.00 0.50 5.77 -- -74.00 -56.00 75.92 70 41 \w -121.00 -86.00 0.50 5.77 -- -74.00 -55.00 153.24 70 42 \w -121.00 -86.00 0.50 5.77 -- -74.00 -58.00 4.19 70 43 \w -124.00 -87.00 0.50 5.77 -- -74.00 -44.00 108.06 74 44 \w -124.00 -87.00 0.50 5.77 -- -74.00 -45.00 121.66 74 45 \w -120.00 -86.00 0.50 5.77 -- -74.00 -59.00 -10.73 68 46 \w -120.00 -86.00 0.50 5.77 -- -74.00 -60.00-139.88 68 47 \w -97.00 -28.00 0.50 5.77 -- -76.37 112.00 -90.00 138 48 \w -126.00 -91.00 0.50 5.77 -- -78.00 -52.00 35.50 70 49 \w -127.00 -91.00 0.50 5.77 -- -79.50 -56.00-159.82 72 50 \w -127.00 -87.00 0.50 5.77 -- -79.50-132.00 117.98 80 51 \w -127.00 -87.00 0.50 5.77 -- -79.50-132.00 163.39 80 52 \w -127.00 -89.00 0.50 5.77 -- -79.50-129.00 -87.02 76 53 \w -128.00 -94.00 0.50 5.77 -- -79.50-118.00-135.53 68 54 \w -127.00 -92.00 0.50 5.77 -- -79.50 -53.00 -62.50 70 55 \w -128.00 -94.00 0.50 5.77 -- -79.50-119.00-174.15 68 56 \w -98.00 -31.00 0.50 5.77 -- -79.50 121.00 114.95 134 57 \w -125.00 -90.00 0.50 5.77 -- -79.50 -62.00 116.47 70 58 \w -128.00 -95.00 0.50 5.77 -- -79.50-117.00 -65.36 66 59 \w -124.00 -92.00 0.50 5.77 -- -79.50 -63.00 -91.96 64 60 \w -128.00 -96.00 0.50 5.77 -- -79.50-115.00 44.04 64 61 \w 34.00 97.00 0.50 5.77 -- 82.31-112.00 90.00 126 62 \w 46.00 133.00 0.50 5.77 -- 82.31 15.00 90.00 174 63 \w 46.00 133.00 0.50 5.77 -- 82.31 15.00 -30.00 174 64 \w 25.00 54.00 0.50 5.77 -- 14.00 61.00-126.22 58 65 \w 34.00 60.00 0.50 5.77 -- 22.00 58.00 20.65 52 66 \w 34.00 60.00 0.50 5.77 -- 22.00 59.00 170.46 52 67 \w 34.00 60.00 0.50 5.77 -- 22.00 59.00 86.34 52 68 \w -124.00 -89.00 0.50 5.77 -- -78.00 -61.00-113.39 70 69 \w -125.00 -90.00 0.50 5.77 -- -79.50 -62.00 -75.63 70 70 \w -125.00 -91.00 0.50 5.77 -- -79.50 -60.00 -15.35 68 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku XtaLAB Synergy-R' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 68531 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.963 _diffrn_reflns_theta_min 3.625 _diffrn_source 'rotating-anode X-ray tube' _diffrn_source_type 'PhotonJet R X-ray Source' _exptl_absorpt_coefficient_mu 0.503 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.73a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.175 _exptl_crystal_description needle _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.103 _exptl_crystal_size_mid 0.041 _exptl_crystal_size_min 0.027 _refine_diff_density_max 0.197 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 337 _refine_ls_number_reflns 5488 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0417 _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^)+(0.0557P)^2^+0.7343P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.1128 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4403 _reflns_number_total 5488 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03817g2.cif _cod_data_source_block 2 _cod_depositor_comments 'Adding full bibliography for 1572071--1572079.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1572072 _shelx_shelxl_version_number 2014/7 _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 0.951 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; MaHa171_NeWi_a.res created by SHELXL-2014/7 TITL MaHa171_NeWi_a.res in P2(1)/c REM Old TITL MaHa171_NeWi in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.136, Rweak 0.025, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C36 N CELL 1.54184 13.2512 14.8632 14.8307 90.000 113.055 90.000 ZERR 4.000 0.0002 0.0001 0.0002 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H B N UNIT 140 120 4 4 TEMP -173 SIZE 0.03 0.04 0.10 L.S. 10 BOND $H LIST 4 acta conf FMAP 2 PLAN 20 WGHT 0.055700 0.734300 FVAR 0.49092 RESI 1 BN B1 3 0.691766 0.410902 0.523687 11.00000 0.03251 0.02879 = 0.03274 -0.00006 0.01185 0.00077 N2 4 0.749976 0.373990 0.619036 11.00000 0.03312 0.02412 = 0.02919 -0.00280 0.00817 -0.00204 C3 1 0.750557 0.281239 0.638950 11.00000 0.03082 0.02577 = 0.03001 -0.00088 0.00949 -0.00040 C4 1 0.688799 0.222481 0.568312 11.00000 0.03071 0.02588 = 0.03027 -0.00117 0.00949 -0.00129 C5 1 0.617953 0.253075 0.470963 11.00000 0.02911 0.03055 = 0.02923 -0.00192 0.01006 -0.00087 C6 1 0.545423 0.193750 0.401469 11.00000 0.03353 0.03113 = 0.03241 -0.00233 0.00951 -0.00304 AFIX 43 H6 2 0.542980 0.132267 0.418004 11.00000 -1.20000 AFIX 0 C7 1 0.477926 0.224162 0.309629 11.00000 0.03372 0.03711 = 0.03242 -0.00436 0.00781 -0.00416 AFIX 43 H7 2 0.429095 0.183535 0.263670 11.00000 -1.20000 AFIX 0 C8 1 0.480826 0.313940 0.283786 11.00000 0.03354 0.04101 = 0.02896 0.00179 0.00643 0.00010 AFIX 43 H8 2 0.434397 0.334518 0.220414 11.00000 -1.20000 AFIX 0 C9 1 0.551565 0.372707 0.350845 11.00000 0.03579 0.03272 = 0.03258 0.00156 0.01029 0.00040 AFIX 43 H9 2 0.553688 0.433712 0.332556 11.00000 -1.20000 AFIX 0 C10 1 0.620769 0.344736 0.445734 11.00000 0.03044 0.03050 = 0.02955 -0.00025 0.01067 0.00086 RESI 0 RESI 2 PH C1 1 0.700149 0.514001 0.500946 11.00000 0.03212 0.02874 = 0.02883 -0.00016 0.00510 -0.00100 C2 1 0.747905 0.538495 0.435484 11.00000 0.03802 0.03350 = 0.03235 0.00061 0.00928 0.00058 AFIX 43 H2 2 0.776563 0.492941 0.407251 11.00000 -1.20000 AFIX 0 C3 1 0.754443 0.627972 0.410730 11.00000 0.03788 0.03850 = 0.03482 0.00570 0.00735 -0.00474 AFIX 43 H3 2 0.788344 0.642991 0.366916 11.00000 -1.20000 AFIX 0 C4 1 0.711440 0.695264 0.450046 11.00000 0.04298 0.02846 = 0.03728 0.00488 0.00104 -0.00285 AFIX 43 H4 2 0.715842 0.756447 0.433410 11.00000 -1.20000 AFIX 0 C5 1 0.662238 0.672649 0.513484 11.00000 0.04895 0.03017 = 0.04341 -0.00147 0.01187 0.00473 AFIX 43 H5 2 0.631453 0.718350 0.539657 11.00000 -1.20000 AFIX 0 C6 1 0.657508 0.583481 0.539231 11.00000 0.04398 0.03273 = 0.03838 0.00108 0.01487 0.00219 AFIX 43 H6 2 0.624523 0.569231 0.583938 11.00000 -1.20000 AFIX 0 RESI 0 RESI 3 PH C1 1 0.826201 0.249321 0.738635 11.00000 0.03272 0.02140 = 0.02969 -0.00382 0.00591 -0.00222 C2 1 0.932661 0.224835 0.754131 11.00000 0.03980 0.04747 = 0.03506 0.00159 0.01303 0.00749 AFIX 43 H2 2 0.957324 0.230572 0.702272 11.00000 -1.20000 AFIX 0 C3 1 1.004017 0.191937 0.844636 11.00000 0.03665 0.05288 = 0.04091 0.00108 0.00852 0.01193 AFIX 43 H3 2 1.076701 0.175348 0.854069 11.00000 -1.20000 AFIX 0 C4 1 0.969445 0.183470 0.920152 11.00000 0.03804 0.03150 = 0.03197 -0.00138 0.00268 0.00181 AFIX 43 H4 2 1.018281 0.161625 0.982095 11.00000 -1.20000 AFIX 0 C5 1 0.863637 0.206769 0.905803 11.00000 0.03876 0.03739 = 0.03195 0.00231 0.00781 -0.00251 AFIX 43 H5 2 0.839337 0.200360 0.957821 11.00000 -1.20000 AFIX 0 C6 1 0.792262 0.239605 0.815605 11.00000 0.03133 0.03805 = 0.03388 0.00309 0.00810 -0.00005 AFIX 43 H6 2 0.719491 0.255572 0.806508 11.00000 -1.20000 AFIX 0 RESI 0 RESI 4 PH C1 1 0.693237 0.123698 0.590123 11.00000 0.03080 0.02722 = 0.02694 -0.00319 0.00487 -0.00344 C2 1 0.642999 0.088617 0.648680 11.00000 0.04646 0.03012 = 0.03865 -0.00537 0.01844 -0.00494 AFIX 43 H2 2 0.605222 0.127763 0.675454 11.00000 -1.20000 AFIX 0 C3 1 0.647062 -0.002954 0.668811 11.00000 0.05579 0.03150 = 0.03904 -0.00211 0.02017 -0.00937 AFIX 43 H3 2 0.612407 -0.025828 0.709277 11.00000 -1.20000 AFIX 0 C4 1 0.701234 -0.060692 0.630228 11.00000 0.04836 0.02635 = 0.03768 -0.00063 0.00977 -0.00413 AFIX 43 H4 2 0.704700 -0.123206 0.644480 11.00000 -1.20000 AFIX 0 C5 1 0.750323 -0.026970 0.570808 11.00000 0.04710 0.03018 = 0.04684 -0.00304 0.01788 0.00183 AFIX 43 H5 2 0.787419 -0.066499 0.543742 11.00000 -1.20000 AFIX 0 C6 1 0.745860 0.064655 0.550230 11.00000 0.04215 0.03140 = 0.04283 0.00015 0.01853 0.00000 AFIX 43 H6 2 0.779141 0.087043 0.508479 11.00000 -1.20000 AFIX 0 RESI 0 RESI 5 MES C1 1 0.803565 0.434046 0.701264 11.00000 0.03703 0.02272 = 0.02736 -0.00137 0.00695 -0.00081 C2 1 0.909898 0.464359 0.722561 11.00000 0.03683 0.02700 = 0.03414 -0.00306 0.00962 -0.00042 C3 1 0.955750 0.523958 0.801097 11.00000 0.03937 0.03114 = 0.03843 -0.00637 0.00944 -0.00526 AFIX 43 H3 2 1.028711 0.544450 0.817492 11.00000 -1.20000 AFIX 0 C4 1 0.898304 0.554191 0.855903 11.00000 0.04871 0.02904 = 0.03445 -0.00529 0.01225 -0.00267 C5 1 0.791820 0.523489 0.831184 11.00000 0.04819 0.02932 = 0.03367 -0.00122 0.01588 0.00194 AFIX 43 H5 2 0.751249 0.544133 0.867611 11.00000 -1.20000 AFIX 0 C6 1 0.742893 0.463238 0.754416 11.00000 0.03893 0.02564 = 0.03145 0.00291 0.01073 0.00139 C7 1 0.974362 0.437527 0.662814 11.00000 0.03895 0.04006 = 0.04453 -0.00965 0.01457 -0.00343 AFIX 137 H7A 2 0.949819 0.473139 0.602404 11.00000 -1.50000 H7B 2 0.962675 0.373474 0.646342 11.00000 -1.50000 H7C 2 1.052554 0.448504 0.700806 11.00000 -1.50000 AFIX 0 C8 1 0.950158 0.618903 0.939941 11.00000 0.05979 0.04331 = 0.04515 -0.01634 0.01807 -0.00870 AFIX 137 H8A 2 1.014002 0.647488 0.934160 11.00000 -1.50000 H8B 2 0.973464 0.586080 1.002108 11.00000 -1.50000 H8C 2 0.896663 0.665142 0.938100 11.00000 -1.50000 AFIX 0 C9 1 0.626449 0.432827 0.728021 11.00000 0.04342 0.03516 = 0.04281 0.00293 0.01802 0.00080 AFIX 137 H9A 2 0.580560 0.454539 0.662269 11.00000 -1.50000 H9B 2 0.599005 0.457189 0.775526 11.00000 -1.50000 H9C 2 0.623965 0.366952 0.729084 11.00000 -1.50000 RESI 0 AFIX 0 HKLF 4 REM MaHa171_NeWi_a.res in P2(1)/c REM R1 = 0.0417 for 4403 Fo > 4sig(Fo) and 0.0542 for all 5488 data REM 337 parameters refined using 0 restraints END WGHT 0.0557 0.7343 REM Highest difference peak 0.197, deepest hole -0.224, 1-sigma level 0.036 Q1 1 0.9277 0.4009 0.5933 11.00000 0.05 0.20 Q2 1 1.0183 0.4903 0.6481 11.00000 0.05 0.19 Q3 1 0.7020 0.4629 0.5132 11.00000 0.05 0.16 Q4 1 0.9531 0.6846 0.9190 11.00000 0.05 0.15 Q5 1 0.6859 0.1714 0.5782 11.00000 0.05 0.14 Q6 1 1.0405 0.6073 0.9791 11.00000 0.05 0.13 Q7 1 0.7975 0.2648 0.6983 11.00000 0.05 0.12 Q8 1 0.6677 0.3747 0.4807 11.00000 0.05 0.12 Q9 1 1.0403 0.3860 0.7064 11.00000 0.05 0.11 Q10 1 0.6114 0.2997 0.4604 11.00000 0.05 0.11 Q11 1 0.8505 0.2462 0.9836 11.00000 0.05 0.11 Q12 1 0.8868 0.6242 0.9798 11.00000 0.05 0.11 Q13 1 0.6830 0.5434 0.5187 11.00000 0.05 0.11 Q14 1 0.6012 0.4037 0.8003 11.00000 0.05 0.10 Q15 1 0.8634 0.4472 0.7186 11.00000 0.05 0.10 Q16 1 0.8170 0.1410 0.9420 11.00000 0.05 0.10 Q17 1 1.0143 0.2437 0.8331 11.00000 0.05 0.10 Q18 1 0.6840 0.2232 0.7977 11.00000 0.05 0.10 Q19 1 0.7322 0.0976 0.5871 11.00000 0.05 0.10 Q20 1 0.5418 0.1341 0.6414 11.00000 0.05 0.10 ; _shelx_res_checksum 12554 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group B1_1 B 0.69177(13) 0.41090(10) 0.52369(11) 0.0316(3) Uani 1 1 d . . . . . N2_1 N 0.74998(9) 0.37399(7) 0.61904(8) 0.0301(2) Uani 1 1 d . . . . . C3_1 C 0.75056(10) 0.28124(8) 0.63895(9) 0.0296(3) Uani 1 1 d . . . . . C4_1 C 0.68880(11) 0.22248(8) 0.56831(9) 0.0297(3) Uani 1 1 d . . . . . C5_1 C 0.61795(10) 0.25308(9) 0.47096(9) 0.0300(3) Uani 1 1 d . . . . . C6_1 C 0.54542(11) 0.19375(9) 0.40147(10) 0.0334(3) Uani 1 1 d . . . . . H6_1 H 0.5430 0.1323 0.4180 0.040 Uiso 1 1 calc R U . . . C7_1 C 0.47793(11) 0.22416(10) 0.30963(10) 0.0360(3) Uani 1 1 d . . . . . H7_1 H 0.4291 0.1835 0.2637 0.043 Uiso 1 1 calc R U . . . C8_1 C 0.48083(11) 0.31394(10) 0.28379(10) 0.0363(3) Uani 1 1 d . . . . . H8_1 H 0.4344 0.3345 0.2204 0.044 Uiso 1 1 calc R U . . . C9_1 C 0.55157(11) 0.37271(10) 0.35084(10) 0.0346(3) Uani 1 1 d . . . . . H9_1 H 0.5537 0.4337 0.3326 0.042 Uiso 1 1 calc R U . . . C10_1 C 0.62077(11) 0.34474(9) 0.44573(9) 0.0305(3) Uani 1 1 d . . . . . C1_2 C 0.70015(11) 0.51400(9) 0.50095(10) 0.0320(3) Uani 1 1 d . . . . . C2_2 C 0.74791(11) 0.53849(9) 0.43548(10) 0.0360(3) Uani 1 1 d . . . . . H2_2 H 0.7766 0.4929 0.4073 0.043 Uiso 1 1 calc R U . . . C3_2 C 0.75444(12) 0.62797(10) 0.41073(10) 0.0392(3) Uani 1 1 d . . . . . H3_2 H 0.7883 0.6430 0.3669 0.047 Uiso 1 1 calc R U . . . C4_2 C 0.71144(12) 0.69526(10) 0.45005(10) 0.0408(3) Uani 1 1 d . . . . . H4_2 H 0.7158 0.7564 0.4334 0.049 Uiso 1 1 calc R U . . . C5_2 C 0.66224(13) 0.67265(10) 0.51348(11) 0.0428(4) Uani 1 1 d . . . . . H5_2 H 0.6315 0.7183 0.5397 0.051 Uiso 1 1 calc R U . . . C6_2 C 0.65751(12) 0.58348(10) 0.53923(11) 0.0388(3) Uani 1 1 d . . . . . H6_2 H 0.6245 0.5692 0.5839 0.047 Uiso 1 1 calc R U . . . C1_3 C 0.82620(11) 0.24932(8) 0.73864(9) 0.0299(3) Uani 1 1 d . . . . . C2_3 C 0.93266(12) 0.22484(10) 0.75413(11) 0.0413(3) Uani 1 1 d . . . . . H2_3 H 0.9573 0.2306 0.7023 0.050 Uiso 1 1 calc R U . . . C3_3 C 1.00402(13) 0.19194(11) 0.84464(11) 0.0455(4) Uani 1 1 d . . . . . H3_3 H 1.0767 0.1753 0.8541 0.055 Uiso 1 1 calc R U . . . C4_3 C 0.96944(12) 0.18347(9) 0.92015(10) 0.0372(3) Uani 1 1 d . . . . . H4_3 H 1.0183 0.1616 0.9821 0.045 Uiso 1 1 calc R U . . . C5_3 C 0.86364(12) 0.20677(10) 0.90580(10) 0.0379(3) Uani 1 1 d . . . . . H5_3 H 0.8393 0.2004 0.9578 0.045 Uiso 1 1 calc R U . . . C6_3 C 0.79226(11) 0.23961(10) 0.81561(10) 0.0359(3) Uani 1 1 d . . . . . H6_3 H 0.7195 0.2556 0.8065 0.043 Uiso 1 1 calc R U . . . C1_4 C 0.69324(10) 0.12370(9) 0.59012(9) 0.0303(3) Uani 1 1 d . . . . . C2_4 C 0.64300(12) 0.08862(9) 0.64868(11) 0.0379(3) Uani 1 1 d . . . . . H2_4 H 0.6052 0.1278 0.6755 0.045 Uiso 1 1 calc R U . . . C3_4 C 0.64706(13) -0.00295(10) 0.66881(11) 0.0416(3) Uani 1 1 d . . . . . H3_4 H 0.6124 -0.0258 0.7093 0.050 Uiso 1 1 calc R U . . . C4_4 C 0.70123(13) -0.06069(9) 0.63023(11) 0.0396(3) Uani 1 1 d . . . . . H4_4 H 0.7047 -0.1232 0.6445 0.048 Uiso 1 1 calc R U . . . C5_4 C 0.75032(13) -0.02697(10) 0.57081(11) 0.0415(3) Uani 1 1 d . . . . . H5_4 H 0.7874 -0.0665 0.5437 0.050 Uiso 1 1 calc R U . . . C6_4 C 0.74586(12) 0.06466(9) 0.55023(11) 0.0382(3) Uani 1 1 d . . . . . H6_4 H 0.7791 0.0870 0.5085 0.046 Uiso 1 1 calc R U . . . C1_5 C 0.80357(11) 0.43405(8) 0.70126(9) 0.0308(3) Uani 1 1 d . . . . . C2_5 C 0.90990(11) 0.46436(9) 0.72256(10) 0.0340(3) Uani 1 1 d . . . . . C3_5 C 0.95575(12) 0.52396(9) 0.80110(10) 0.0381(3) Uani 1 1 d . . . . . H3_5 H 1.0287 0.5445 0.8175 0.046 Uiso 1 1 calc R U . . . C4_5 C 0.89830(13) 0.55419(9) 0.85590(11) 0.0386(3) Uani 1 1 d . . . . . C5_5 C 0.79182(12) 0.52349(9) 0.83118(10) 0.0371(3) Uani 1 1 d . . . . . H5_5 H 0.7512 0.5441 0.8676 0.045 Uiso 1 1 calc R U . . . C6_5 C 0.74289(11) 0.46324(9) 0.75442(10) 0.0329(3) Uani 1 1 d . . . . . C7_5 C 0.97436(12) 0.43753(11) 0.66281(11) 0.0417(3) Uani 1 1 d . . . . . H7A_5 H 0.9498 0.4731 0.6024 0.063 Uiso 1 1 calc R U . . . H7B_5 H 0.9627 0.3735 0.6463 0.063 Uiso 1 1 calc R U . . . H7C_5 H 1.0526 0.4485 0.7008 0.063 Uiso 1 1 calc R U . . . C8_5 C 0.95016(15) 0.61890(11) 0.93994(12) 0.0502(4) Uani 1 1 d . . . . . H8A_5 H 1.0140 0.6475 0.9342 0.075 Uiso 1 1 calc R U . . . H8B_5 H 0.9735 0.5861 1.0021 0.075 Uiso 1 1 calc R U . . . H8C_5 H 0.8967 0.6651 0.9381 0.075 Uiso 1 1 calc R U . . . C9_5 C 0.62645(12) 0.43283(10) 0.72802(11) 0.0401(3) Uani 1 1 d . . . . . H9A_5 H 0.5806 0.4545 0.6623 0.060 Uiso 1 1 calc R U . . . H9B_5 H 0.5990 0.4572 0.7755 0.060 Uiso 1 1 calc R U . . . H9C_5 H 0.6240 0.3670 0.7291 0.060 Uiso 1 1 calc R U . . . 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 B1_1 0.0325(7) 0.0288(7) 0.0327(8) -0.0001(6) 0.0118(6) 0.0008(6) N2_1 0.0331(6) 0.0241(5) 0.0292(6) -0.0028(4) 0.0082(5) -0.0020(4) C3_1 0.0308(6) 0.0258(6) 0.0300(7) -0.0009(5) 0.0095(5) -0.0004(5) C4_1 0.0307(6) 0.0259(6) 0.0303(7) -0.0012(5) 0.0095(5) -0.0013(5) C5_1 0.0291(6) 0.0305(7) 0.0292(7) -0.0019(5) 0.0101(5) -0.0009(5) C6_1 0.0335(7) 0.0311(7) 0.0324(7) -0.0023(5) 0.0095(6) -0.0030(5) C7_1 0.0337(7) 0.0371(7) 0.0324(7) -0.0044(6) 0.0078(6) -0.0042(6) C8_1 0.0335(7) 0.0410(8) 0.0290(7) 0.0018(6) 0.0064(6) 0.0001(6) C9_1 0.0358(7) 0.0327(7) 0.0326(7) 0.0016(6) 0.0103(6) 0.0004(6) C10_1 0.0304(6) 0.0305(7) 0.0296(7) -0.0003(5) 0.0107(5) 0.0009(5) C1_2 0.0321(7) 0.0287(7) 0.0288(7) -0.0002(5) 0.0051(5) -0.0010(5) C2_2 0.0380(7) 0.0335(7) 0.0324(7) 0.0006(6) 0.0093(6) 0.0006(6) C3_2 0.0379(7) 0.0385(8) 0.0348(7) 0.0057(6) 0.0074(6) -0.0047(6) C4_2 0.0430(8) 0.0285(7) 0.0373(8) 0.0049(6) 0.0010(6) -0.0029(6) C5_2 0.0490(9) 0.0302(7) 0.0434(8) -0.0015(6) 0.0119(7) 0.0047(6) C6_2 0.0440(8) 0.0327(7) 0.0384(8) 0.0011(6) 0.0149(6) 0.0022(6) C1_3 0.0327(6) 0.0214(6) 0.0297(7) -0.0038(5) 0.0059(5) -0.0022(5) C2_3 0.0398(8) 0.0475(9) 0.0351(8) 0.0016(6) 0.0130(6) 0.0075(6) C3_3 0.0366(8) 0.0529(9) 0.0409(8) 0.0011(7) 0.0085(6) 0.0119(7) C4_3 0.0380(7) 0.0315(7) 0.0320(7) -0.0014(6) 0.0027(6) 0.0018(6) C5_3 0.0388(7) 0.0374(8) 0.0320(7) 0.0023(6) 0.0078(6) -0.0025(6) C6_3 0.0313(7) 0.0380(7) 0.0339(7) 0.0031(6) 0.0081(6) -0.0001(6) C1_4 0.0308(6) 0.0272(6) 0.0269(6) -0.0032(5) 0.0049(5) -0.0034(5) C2_4 0.0465(8) 0.0301(7) 0.0387(8) -0.0054(6) 0.0184(6) -0.0049(6) C3_4 0.0558(9) 0.0315(7) 0.0390(8) -0.0021(6) 0.0202(7) -0.0094(6) C4_4 0.0484(8) 0.0263(7) 0.0377(8) -0.0006(6) 0.0098(6) -0.0041(6) C5_4 0.0471(8) 0.0302(7) 0.0468(9) -0.0030(6) 0.0179(7) 0.0018(6) C6_4 0.0421(8) 0.0314(7) 0.0428(8) 0.0001(6) 0.0185(6) 0.0000(6) C1_5 0.0370(7) 0.0227(6) 0.0274(6) -0.0014(5) 0.0069(5) -0.0008(5) C2_5 0.0368(7) 0.0270(6) 0.0341(7) -0.0031(5) 0.0096(6) -0.0004(5) C3_5 0.0394(7) 0.0311(7) 0.0384(8) -0.0064(6) 0.0094(6) -0.0053(6) C4_5 0.0487(8) 0.0290(7) 0.0344(7) -0.0053(6) 0.0123(6) -0.0027(6) C5_5 0.0482(8) 0.0293(7) 0.0337(7) -0.0012(6) 0.0159(6) 0.0019(6) C6_5 0.0389(7) 0.0256(6) 0.0315(7) 0.0029(5) 0.0107(6) 0.0014(5) C7_5 0.0390(8) 0.0401(8) 0.0445(8) -0.0096(6) 0.0146(7) -0.0034(6) C8_5 0.0598(10) 0.0433(9) 0.0451(9) -0.0163(7) 0.0181(8) -0.0087(7) C9_5 0.0434(8) 0.0352(7) 0.0428(8) 0.0029(6) 0.0180(7) 0.0008(6) 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 -1 -2 1 0.0410 -1 2 -2 0.0188 -2 0 -1 0.0147 -2 1 -1 0.0096 1 0 0 0.0204 -1 0 0 0.0065 2 -1 0 0.0270 -2 1 0 0.0056 0 -2 1 0.0438 1 -1 0 0.0295 2 0 -1 0.0346 1 1 -1 0.0259 -2 0 1 0.0288 1 -2 0 0.0319 0 2 1 0.0120 0 -2 -1 0.0338 -1 -2 0 0.0308 1 2 0 0.0010 0 -1 2 0.0461 0 1 -2 0.0344 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 N2_1 B1_1 C10_1 115.80(12) . . ? N2_1 B1_1 C1_2 121.81(12) . . ? C10_1 B1_1 C1_2 122.39(12) . . ? C3_1 N2_1 B1_1 122.66(11) . . ? C3_1 N2_1 C1_5 117.67(10) . . ? B1_1 N2_1 C1_5 119.47(11) . . ? C4_1 C3_1 N2_1 120.88(11) . . ? C4_1 C3_1 C1_3 121.51(11) . . ? N2_1 C3_1 C1_3 117.53(11) . . ? C3_1 C4_1 C5_1 121.53(12) . . ? C3_1 C4_1 C1_4 120.03(11) . . ? C5_1 C4_1 C1_4 118.44(11) . . ? C6_1 C5_1 C10_1 119.28(12) . . ? C6_1 C5_1 C4_1 121.39(12) . . ? C10_1 C5_1 C4_1 119.32(11) . . ? C7_1 C6_1 C5_1 120.62(13) . . ? C7_1 C6_1 H6_1 119.7 . . ? C5_1 C6_1 H6_1 119.7 . . ? C6_1 C7_1 C8_1 120.54(13) . . ? C6_1 C7_1 H7_1 119.7 . . ? C8_1 C7_1 H7_1 119.7 . . ? C9_1 C8_1 C7_1 119.52(13) . . ? C9_1 C8_1 H8_1 120.2 . . ? C7_1 C8_1 H8_1 120.2 . . ? C8_1 C9_1 C10_1 121.77(13) . . ? C8_1 C9_1 H9_1 119.1 . . ? C10_1 C9_1 H9_1 119.1 . . ? C9_1 C10_1 C5_1 118.26(12) . . ? C9_1 C10_1 B1_1 122.20(12) . . ? C5_1 C10_1 B1_1 119.39(12) . . ? C2_2 C1_2 C6_2 116.98(13) . . ? C2_2 C1_2 B1_1 119.25(12) . . ? C6_2 C1_2 B1_1 123.70(13) . . ? C3_2 C2_2 C1_2 121.58(14) . . ? C3_2 C2_2 H2_2 119.2 . . ? C1_2 C2_2 H2_2 119.2 . . ? C4_2 C3_2 C2_2 119.99(14) . . ? C4_2 C3_2 H3_2 120.0 . . ? C2_2 C3_2 H3_2 120.0 . . ? C5_2 C4_2 C3_2 119.50(13) . . ? C5_2 C4_2 H4_2 120.2 . . ? C3_2 C4_2 H4_2 120.2 . . ? C4_2 C5_2 C6_2 120.31(14) . . ? C4_2 C5_2 H5_2 119.8 . . ? C6_2 C5_2 H5_2 119.8 . . ? C5_2 C6_2 C1_2 121.61(14) . . ? C5_2 C6_2 H6_2 119.2 . . ? C1_2 C6_2 H6_2 119.2 . . ? C2_3 C1_3 C6_3 118.20(12) . . ? C2_3 C1_3 C3_1 119.33(12) . . ? C6_3 C1_3 C3_1 122.41(12) . . ? C1_3 C2_3 C3_3 120.97(14) . . ? C1_3 C2_3 H2_3 119.5 . . ? C3_3 C2_3 H2_3 119.5 . . ? C4_3 C3_3 C2_3 120.08(14) . . ? C4_3 C3_3 H3_3 120.0 . . ? C2_3 C3_3 H3_3 120.0 . . ? C3_3 C4_3 C5_3 119.73(13) . . ? C3_3 C4_3 H4_3 120.1 . . ? C5_3 C4_3 H4_3 120.1 . . ? C4_3 C5_3 C6_3 120.32(14) . . ? C4_3 C5_3 H5_3 119.8 . . ? C6_3 C5_3 H5_3 119.8 . . ? C1_3 C6_3 C5_3 120.69(13) . . ? C1_3 C6_3 H6_3 119.7 . . ? C5_3 C6_3 H6_3 119.7 . . ? C2_4 C1_4 C6_4 118.26(13) . . ? C2_4 C1_4 C4_1 121.03(12) . . ? C6_4 C1_4 C4_1 120.70(12) . . ? C1_4 C2_4 C3_4 121.01(14) . . ? C1_4 C2_4 H2_4 119.5 . . ? C3_4 C2_4 H2_4 119.5 . . ? C4_4 C3_4 C2_4 120.20(14) . . ? C4_4 C3_4 H3_4 119.9 . . ? C2_4 C3_4 H3_4 119.9 . . ? C5_4 C4_4 C3_4 119.46(13) . . ? C5_4 C4_4 H4_4 120.3 . . ? C3_4 C4_4 H4_4 120.3 . . ? C4_4 C5_4 C6_4 120.39(14) . . ? C4_4 C5_4 H5_4 119.8 . . ? C6_4 C5_4 H5_4 119.8 . . ? C1_4 C6_4 C5_4 120.67(14) . . ? C1_4 C6_4 H6_4 119.7 . . ? C5_4 C6_4 H6_4 119.7 . . ? C2_5 C1_5 C6_5 121.75(12) . . ? C2_5 C1_5 N2_1 120.52(12) . . ? C6_5 C1_5 N2_1 117.67(12) . . ? C1_5 C2_5 C3_5 117.69(13) . . ? C1_5 C2_5 C7_5 122.52(12) . . ? C3_5 C2_5 C7_5 119.76(13) . . ? C4_5 C3_5 C2_5 122.25(13) . . ? C4_5 C3_5 H3_5 118.9 . . ? C2_5 C3_5 H3_5 118.9 . . ? C3_5 C4_5 C5_5 118.20(13) . . ? C3_5 C4_5 C8_5 120.86(14) . . ? C5_5 C4_5 C8_5 120.94(14) . . ? C4_5 C5_5 C6_5 121.77(13) . . ? C4_5 C5_5 H5_5 119.1 . . ? C6_5 C5_5 H5_5 119.1 . . ? C5_5 C6_5 C1_5 118.31(13) . . ? C5_5 C6_5 C9_5 120.48(13) . . ? C1_5 C6_5 C9_5 121.18(12) . . ? C2_5 C7_5 H7A_5 109.5 . . ? C2_5 C7_5 H7B_5 109.5 . . ? H7A_5 C7_5 H7B_5 109.5 . . ? C2_5 C7_5 H7C_5 109.5 . . ? H7A_5 C7_5 H7C_5 109.5 . . ? H7B_5 C7_5 H7C_5 109.5 . . ? C4_5 C8_5 H8A_5 109.5 . . ? C4_5 C8_5 H8B_5 109.5 . . ? H8A_5 C8_5 H8B_5 109.5 . . ? C4_5 C8_5 H8C_5 109.5 . . ? H8A_5 C8_5 H8C_5 109.5 . . ? H8B_5 C8_5 H8C_5 109.5 . . ? C6_5 C9_5 H9A_5 109.5 . . ? C6_5 C9_5 H9B_5 109.5 . . ? H9A_5 C9_5 H9B_5 109.5 . . ? C6_5 C9_5 H9C_5 109.5 . . ? H9A_5 C9_5 H9C_5 109.5 . . ? H9B_5 C9_5 H9C_5 109.5 . . ? 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 B1_1 N2_1 1.4287(18) . ? B1_1 C10_1 1.529(2) . ? B1_1 C1_2 1.582(2) . ? N2_1 C3_1 1.4093(16) . ? N2_1 C1_5 1.4526(16) . ? C3_1 C4_1 1.3632(18) . ? C3_1 C1_3 1.5016(17) . ? C4_1 C5_1 1.4529(18) . ? C4_1 C1_4 1.4996(17) . ? C5_1 C6_1 1.4098(18) . ? C5_1 C10_1 1.4172(18) . ? C6_1 C7_1 1.3803(19) . ? C6_1 H6_1 0.9500 . ? C7_1 C8_1 1.393(2) . ? C7_1 H7_1 0.9500 . ? C8_1 C9_1 1.3786(19) . ? C8_1 H8_1 0.9500 . ? C9_1 C10_1 1.4083(18) . ? C9_1 H9_1 0.9500 . ? C1_2 C2_2 1.399(2) . ? C1_2 C6_2 1.400(2) . ? C2_2 C3_2 1.391(2) . ? C2_2 H2_2 0.9500 . ? C3_2 C4_2 1.388(2) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.380(2) . ? C4_2 H4_2 0.9500 . ? C5_2 C6_2 1.387(2) . ? C5_2 H5_2 0.9500 . ? C6_2 H6_2 0.9500 . ? C1_3 C2_3 1.3862(19) . ? C1_3 C6_3 1.3886(19) . ? C2_3 C3_3 1.393(2) . ? C2_3 H2_3 0.9500 . ? C3_3 C4_3 1.372(2) . ? C3_3 H3_3 0.9500 . ? C4_3 C5_3 1.377(2) . ? C4_3 H4_3 0.9500 . ? C5_3 C6_3 1.3897(19) . ? C5_3 H5_3 0.9500 . ? C6_3 H6_3 0.9500 . ? C1_4 C2_4 1.3864(19) . ? C1_4 C6_4 1.3891(19) . ? C2_4 C3_4 1.390(2) . ? C2_4 H2_4 0.9500 . ? C3_4 C4_4 1.379(2) . ? C3_4 H3_4 0.9500 . ? C4_4 C5_4 1.378(2) . ? C4_4 H4_4 0.9500 . ? C5_4 C6_4 1.392(2) . ? C5_4 H5_4 0.9500 . ? C6_4 H6_4 0.9500 . ? C1_5 C2_5 1.3927(19) . ? C1_5 C6_5 1.3973(19) . ? C2_5 C3_5 1.3986(19) . ? C2_5 C7_5 1.506(2) . ? C3_5 C4_5 1.388(2) . ? C3_5 H3_5 0.9500 . ? C4_5 C5_5 1.389(2) . ? C4_5 C8_5 1.510(2) . ? C5_5 C6_5 1.3930(19) . ? C5_5 H5_5 0.9500 . ? C6_5 C9_5 1.5051(19) . ? C7_5 H7A_5 0.9800 . ? C7_5 H7B_5 0.9800 . ? C7_5 H7C_5 0.9800 . ? C8_5 H8A_5 0.9800 . ? C8_5 H8B_5 0.9800 . ? C8_5 H8C_5 0.9800 . ? C9_5 H9A_5 0.9800 . ? C9_5 H9B_5 0.9800 . ? C9_5 H9C_5 0.9800 . ? 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_1 B1_1 N2_1 C3_1 5.52(19) . . . . ? C1_2 B1_1 N2_1 C3_1 -174.83(12) . . . . ? C10_1 B1_1 N2_1 C1_5 -169.16(12) . . . . ? C1_2 B1_1 N2_1 C1_5 10.49(19) . . . . ? B1_1 N2_1 C3_1 C4_1 -4.4(2) . . . . ? C1_5 N2_1 C3_1 C4_1 170.42(12) . . . . ? B1_1 N2_1 C3_1 C1_3 172.30(12) . . . . ? C1_5 N2_1 C3_1 C1_3 -12.93(17) . . . . ? N2_1 C3_1 C4_1 C5_1 -1.7(2) . . . . ? C1_3 C3_1 C4_1 C5_1 -178.22(12) . . . . ? N2_1 C3_1 C4_1 C1_4 178.13(12) . . . . ? C1_3 C3_1 C4_1 C1_4 1.6(2) . . . . ? C3_1 C4_1 C5_1 C6_1 -173.07(13) . . . . ? C1_4 C4_1 C5_1 C6_1 7.11(19) . . . . ? C3_1 C4_1 C5_1 C10_1 6.1(2) . . . . ? C1_4 C4_1 C5_1 C10_1 -173.72(12) . . . . ? C10_1 C5_1 C6_1 C7_1 0.2(2) . . . . ? C4_1 C5_1 C6_1 C7_1 179.37(13) . . . . ? C5_1 C6_1 C7_1 C8_1 0.4(2) . . . . ? C6_1 C7_1 C8_1 C9_1 -0.2(2) . . . . ? C7_1 C8_1 C9_1 C10_1 -0.6(2) . . . . ? C8_1 C9_1 C10_1 C5_1 1.2(2) . . . . ? C8_1 C9_1 C10_1 B1_1 -174.27(13) . . . . ? C6_1 C5_1 C10_1 C9_1 -0.99(19) . . . . ? C4_1 C5_1 C10_1 C9_1 179.82(12) . . . . ? C6_1 C5_1 C10_1 B1_1 174.64(12) . . . . ? C4_1 C5_1 C10_1 B1_1 -4.55(19) . . . . ? N2_1 B1_1 C10_1 C9_1 174.47(12) . . . . ? C1_2 B1_1 C10_1 C9_1 -5.2(2) . . . . ? N2_1 B1_1 C10_1 C5_1 -0.98(19) . . . . ? C1_2 B1_1 C10_1 C5_1 179.37(12) . . . . ? N2_1 B1_1 C1_2 C2_2 115.03(15) . . . . ? C10_1 B1_1 C1_2 C2_2 -65.34(18) . . . . ? N2_1 B1_1 C1_2 C6_2 -68.13(19) . . . . ? C10_1 B1_1 C1_2 C6_2 111.51(16) . . . . ? C6_2 C1_2 C2_2 C3_2 1.0(2) . . . . ? B1_1 C1_2 C2_2 C3_2 178.10(13) . . . . ? C1_2 C2_2 C3_2 C4_2 -1.0(2) . . . . ? C2_2 C3_2 C4_2 C5_2 -0.1(2) . . . . ? C3_2 C4_2 C5_2 C6_2 1.2(2) . . . . ? C4_2 C5_2 C6_2 C1_2 -1.1(2) . . . . ? C2_2 C1_2 C6_2 C5_2 0.0(2) . . . . ? B1_1 C1_2 C6_2 C5_2 -176.87(14) . . . . ? C4_1 C3_1 C1_3 C2_3 87.60(17) . . . . ? N2_1 C3_1 C1_3 C2_3 -89.03(16) . . . . ? C4_1 C3_1 C1_3 C6_3 -89.59(17) . . . . ? N2_1 C3_1 C1_3 C6_3 93.78(15) . . . . ? C6_3 C1_3 C2_3 C3_3 -0.4(2) . . . . ? C3_1 C1_3 C2_3 C3_3 -177.74(13) . . . . ? C1_3 C2_3 C3_3 C4_3 -0.1(2) . . . . ? C2_3 C3_3 C4_3 C5_3 0.6(2) . . . . ? C3_3 C4_3 C5_3 C6_3 -0.6(2) . . . . ? C2_3 C1_3 C6_3 C5_3 0.4(2) . . . . ? C3_1 C1_3 C6_3 C5_3 177.65(12) . . . . ? C4_3 C5_3 C6_3 C1_3 0.1(2) . . . . ? C3_1 C4_1 C1_4 C2_4 73.77(17) . . . . ? C5_1 C4_1 C1_4 C2_4 -106.40(15) . . . . ? C3_1 C4_1 C1_4 C6_4 -107.69(16) . . . . ? C5_1 C4_1 C1_4 C6_4 72.14(17) . . . . ? C6_4 C1_4 C2_4 C3_4 1.4(2) . . . . ? C4_1 C1_4 C2_4 C3_4 179.95(13) . . . . ? C1_4 C2_4 C3_4 C4_4 -0.2(2) . . . . ? C2_4 C3_4 C4_4 C5_4 -0.6(2) . . . . ? C3_4 C4_4 C5_4 C6_4 0.3(2) . . . . ? C2_4 C1_4 C6_4 C5_4 -1.7(2) . . . . ? C4_1 C1_4 C6_4 C5_4 179.75(13) . . . . ? C4_4 C5_4 C6_4 C1_4 0.8(2) . . . . ? C3_1 N2_1 C1_5 C2_5 98.37(15) . . . . ? B1_1 N2_1 C1_5 C2_5 -86.68(16) . . . . ? C3_1 N2_1 C1_5 C6_5 -84.66(15) . . . . ? B1_1 N2_1 C1_5 C6_5 90.28(15) . . . . ? C6_5 C1_5 C2_5 C3_5 1.5(2) . . . . ? N2_1 C1_5 C2_5 C3_5 178.32(12) . . . . ? C6_5 C1_5 C2_5 C7_5 -176.68(13) . . . . ? N2_1 C1_5 C2_5 C7_5 0.2(2) . . . . ? C1_5 C2_5 C3_5 C4_5 -1.2(2) . . . . ? C7_5 C2_5 C3_5 C4_5 177.03(14) . . . . ? C2_5 C3_5 C4_5 C5_5 0.1(2) . . . . ? C2_5 C3_5 C4_5 C8_5 -179.70(14) . . . . ? C3_5 C4_5 C5_5 C6_5 0.7(2) . . . . ? C8_5 C4_5 C5_5 C6_5 -179.48(14) . . . . ? C4_5 C5_5 C6_5 C1_5 -0.4(2) . . . . ? C4_5 C5_5 C6_5 C9_5 -178.64(13) . . . . ? C2_5 C1_5 C6_5 C5_5 -0.7(2) . . . . ? N2_1 C1_5 C6_5 C5_5 -177.65(12) . . . . ? C2_5 C1_5 C6_5 C9_5 177.50(13) . . . . ? N2_1 C1_5 C6_5 C9_5 0.58(18) . . . . ?