#------------------------------------------------------------------------------ #$Date: 2020-05-05 04:21:52 +0300 (Tue, 05 May 2020) $ #$Revision: 251513 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557998.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_1557998 loop_ _publ_author_name 'Wang, Bin' 'Ong, Derek Yiren' 'Li, Yihang' 'Pang, Jia Hao' 'Watanabe, Kohei' 'TAKITA, Ryo' 'Chiba, Shunsuke' _publ_section_title ; Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01773F _journal_year 2020 _chemical_formula_sum 'C24 H25 N O' _chemical_formula_weight 343.45 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_update_record ; 2020-03-03 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.8945(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.9769(3) _cell_length_b 5.9444(2) _cell_length_c 26.8450(8) _cell_measurement_reflns_used 3704 _cell_measurement_temperature 100.(2) _cell_measurement_theta_max 31.8938 _cell_measurement_theta_min 2.7753 _cell_volume 1908.80(10) _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_collection 'APEX3 (Bruker AXS Inc., 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_molecular_graphics 'XP (Bruker AXS Inc., 2018)' _computing_publication_material 'APEX3 (Bruker AXS Inc., 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'XT, VERSION 2014/5' _diffrn_ambient_temperature 100.(2) _diffrn_detector_area_resol_mean 7.4074 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Photon II CPADs detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator 'Multilayer Mirror' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0802 _diffrn_reflns_av_unetI/netI 0.0972 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 25046 _diffrn_reflns_theta_full 33.72 _diffrn_reflns_theta_max 33.72 _diffrn_reflns_theta_min 2.77 _diffrn_source 'Incoatec microfocus source' _diffrn_source_type 'Bruker D8 Quest' _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.301 _refine_diff_density_min -0.244 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 7594 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0695 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.6051P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1231 _refine_ls_wR_factor_ref 0.1550 _reflns_number_gt 4119 _reflns_number_total 7594 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01773f2.cif _cod_data_source_block chiba446m _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 1557998 _shelx_res_file ; TITL chiba446m in P2(1)/n chiba446m.res created by SHELXL-2018/3 at 11:13:18 on 13-Jan-2020 CELL 0.71073 11.97690 5.94440 26.84500 90.0000 92.8945 90.0000 ZERR 4.00 0.00030 0.00020 0.00080 0.0000 0.0013 0.0000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 96 100 4 4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.12 0.20 0.24 TEMP -173.0 WGHT 0.040700 0.605100 FVAR 0.22085 C1 1 0.396361 1.141926 0.566892 11.00000 0.02776 0.02803 = 0.03520 0.00676 0.00220 0.00251 AFIX 43 H1 2 0.414504 1.265807 0.588145 11.00000 -1.20000 AFIX 0 C2 1 0.307187 1.158168 0.531893 11.00000 0.02625 0.03959 = 0.04590 0.01641 -0.00035 0.00608 AFIX 43 H2 2 0.264220 1.292415 0.529473 11.00000 -1.20000 AFIX 0 C3 1 0.281047 0.979588 0.500686 11.00000 0.02612 0.05028 = 0.04038 0.01966 -0.00791 -0.00373 AFIX 43 H3 2 0.219538 0.989979 0.477032 11.00000 -1.20000 AFIX 0 C4 1 0.344725 0.784613 0.503879 11.00000 0.03479 0.03996 = 0.03162 0.00768 -0.00832 -0.00845 AFIX 43 H4 2 0.327542 0.662475 0.481991 11.00000 -1.20000 AFIX 0 C5 1 0.433597 0.767625 0.539032 11.00000 0.02784 0.02858 = 0.02679 0.00457 -0.00284 -0.00160 AFIX 43 H5 2 0.476880 0.633728 0.541139 11.00000 -1.20000 AFIX 0 C6 1 0.459284 0.945216 0.571005 11.00000 0.02222 0.02455 = 0.02536 0.00572 0.00081 0.00008 C7 1 0.553969 0.932503 0.609884 11.00000 0.02466 0.01871 = 0.02752 0.00187 -0.00087 0.00046 AFIX 23 H7A 2 0.618472 1.019822 0.598685 11.00000 -1.20000 H7B 2 0.530313 0.999260 0.641451 11.00000 -1.20000 AFIX 0 C8 1 0.671377 0.689314 0.657589 11.00000 0.02496 0.02111 = 0.02492 0.00003 -0.00570 -0.00208 AFIX 23 H8A 2 0.640663 0.737891 0.689409 11.00000 -1.20000 H8B 2 0.734416 0.789983 0.650401 11.00000 -1.20000 AFIX 0 C9 1 0.712429 0.450605 0.662269 11.00000 0.02408 0.02239 = 0.02204 -0.00177 -0.00706 -0.00107 C10 1 0.807242 0.386572 0.631750 11.00000 0.02314 0.02321 = 0.02210 -0.00247 -0.00473 -0.00376 C11 1 0.828378 0.510367 0.588910 11.00000 0.02730 0.03046 = 0.02665 0.00365 -0.00365 0.00182 AFIX 43 H11 2 0.781221 0.633692 0.579782 11.00000 -1.20000 AFIX 0 C12 1 0.916240 0.457526 0.559546 11.00000 0.03326 0.04300 = 0.02793 0.00974 0.00355 0.00408 AFIX 43 H12 2 0.928618 0.544477 0.530650 11.00000 -1.20000 AFIX 0 C13 1 0.986310 0.278748 0.571969 11.00000 0.02790 0.04593 = 0.03096 0.00476 0.00429 0.00500 AFIX 43 H13 2 1.046586 0.242268 0.551745 11.00000 -1.20000 AFIX 0 C14 1 0.967385 0.153693 0.614287 11.00000 0.02705 0.03145 = 0.03210 0.00142 -0.00308 0.00472 AFIX 43 H14 2 1.014906 0.030424 0.623033 11.00000 -1.20000 AFIX 0 C15 1 0.879873 0.206800 0.643918 11.00000 0.02610 0.02470 = 0.02580 0.00131 -0.00254 -0.00165 AFIX 43 H15 2 0.868677 0.120255 0.672994 11.00000 -1.20000 AFIX 0 C16 1 0.667543 0.303148 0.693657 11.00000 0.02350 0.02055 = 0.02322 -0.00168 -0.00631 0.00067 AFIX 43 H16 2 0.704441 0.161750 0.695790 11.00000 -1.20000 AFIX 0 C17 1 0.571590 0.323450 0.725067 11.00000 0.02387 0.02222 = 0.02225 -0.00151 -0.00314 -0.00093 C18 1 0.482271 0.475924 0.718058 11.00000 0.02683 0.02287 = 0.02604 0.00258 -0.00448 0.00002 AFIX 43 H18 2 0.482030 0.577676 0.690764 11.00000 -1.20000 AFIX 0 C19 1 0.395137 0.481803 0.749672 11.00000 0.02340 0.02362 = 0.02828 0.00091 -0.00318 0.00350 AFIX 43 H19 2 0.336906 0.588615 0.743924 11.00000 -1.20000 AFIX 0 C20 1 0.390598 0.332749 0.790337 11.00000 0.02343 0.02444 = 0.02293 -0.00171 -0.00329 -0.00022 C21 1 0.477618 0.175093 0.796525 11.00000 0.02655 0.02487 = 0.02325 0.00307 -0.00500 0.00182 AFIX 43 H21 2 0.476759 0.069542 0.823075 11.00000 -1.20000 AFIX 0 C22 1 0.563896 0.171498 0.764719 11.00000 0.02464 0.02378 = 0.02439 0.00021 -0.00391 0.00361 AFIX 43 H22 2 0.620810 0.061356 0.769793 11.00000 -1.20000 AFIX 0 C23 1 0.299107 0.184392 0.863309 11.00000 0.03269 0.03518 = 0.03117 0.00353 0.00457 -0.00115 AFIX 137 H23A 2 0.293601 0.030128 0.850544 11.00000 -1.50000 H23B 2 0.233465 0.218331 0.882341 11.00000 -1.50000 H23C 2 0.366926 0.199553 0.885042 11.00000 -1.50000 AFIX 0 C24 1 0.217832 0.510319 0.815548 11.00000 0.03156 0.03792 = 0.03624 -0.00153 0.00328 0.00825 AFIX 137 H24A 2 0.252466 0.659719 0.816037 11.00000 -1.50000 H24B 2 0.166518 0.498975 0.842740 11.00000 -1.50000 H24C 2 0.176284 0.487441 0.783560 11.00000 -1.50000 AFIX 0 N1 3 0.304029 0.339821 0.821927 11.00000 0.02749 0.03783 = 0.02570 0.00640 0.00273 0.00699 O1 4 0.586322 0.704929 0.618140 11.00000 0.02764 0.01931 = 0.02531 0.00141 -0.00807 0.00084 HKLF 4 REM chiba446m in P2(1)/n REM wR2 = 0.155023, GooF = S = 1.02473, Restrained GooF = 1.02473 for all data REM R1 = 0.069549 for 4119 Fo > 4sig(Fo) and 0.144738 for all 7594 data REM 237 parameters refined using 0 restraints END WGHT 0.0402 0.6047 REM Highest difference peak 0.301, deepest hole -0.244, 1-sigma level 0.056 Q1 1 0.5617 0.2717 0.7514 11.00000 0.05 0.30 Q2 1 0.5045 0.9349 0.5888 11.00000 0.05 0.30 Q3 1 0.6741 0.5513 0.6619 11.00000 0.05 0.29 Q4 1 0.5549 0.4544 0.7248 11.00000 0.05 0.28 Q5 1 0.5207 0.3538 0.7129 11.00000 0.05 0.26 ; _shelx_res_checksum 54875 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.39636(13) 1.1419(3) 0.56689(6) 0.0303(4) Uani d . . . 1 . . H H1 0.414504 1.265807 0.588145 0.036 Uiso calc U . R 1 . . C C2 0.30719(13) 1.1582(3) 0.53189(7) 0.0373(4) Uani d . . . 1 . . H H2 0.26422 1.292415 0.529473 0.045 Uiso calc U . R 1 . . C C3 0.28105(14) 0.9796(3) 0.50069(7) 0.0393(5) Uani d . . . 1 . . H H3 0.219538 0.989979 0.477032 0.047 Uiso calc U . R 1 . . C C4 0.34472(14) 0.7846(3) 0.50388(7) 0.0358(4) Uani d . . . 1 . . H H4 0.327542 0.662475 0.481991 0.043 Uiso calc U . R 1 . . C C5 0.43360(13) 0.7676(3) 0.53903(6) 0.0279(3) Uani d . . . 1 . . H H5 0.47688 0.633728 0.541139 0.033 Uiso calc U . R 1 . . C C6 0.45928(12) 0.9452(3) 0.57100(6) 0.0241(3) Uani d . . . 1 . . C C7 0.55397(12) 0.9325(2) 0.60988(6) 0.0237(3) Uani d . . . 1 . . H H7A 0.618472 1.019822 0.598685 0.028 Uiso calc U . R 1 . . H H7B 0.530313 0.99926 0.641451 0.028 Uiso calc U . R 1 . . C C8 0.67138(12) 0.6893(2) 0.65759(6) 0.0239(3) Uani d . . . 1 . . H H8A 0.640663 0.737891 0.689409 0.029 Uiso calc U . R 1 . . H H8B 0.734416 0.789983 0.650401 0.029 Uiso calc U . R 1 . . C C9 0.71243(12) 0.4506(2) 0.66227(6) 0.0231(3) Uani d . . . 1 . . C C10 0.80724(12) 0.3866(2) 0.63175(6) 0.0230(3) Uani d . . . 1 . . C C11 0.82838(13) 0.5104(3) 0.58891(6) 0.0283(3) Uani d . . . 1 . . H H11 0.781221 0.633692 0.579782 0.034 Uiso calc U . R 1 . . C C12 0.91624(14) 0.4575(3) 0.55955(6) 0.0347(4) Uani d . . . 1 . . H H12 0.928618 0.544477 0.53065 0.042 Uiso calc U . R 1 . . C C13 0.98631(14) 0.2787(3) 0.57197(6) 0.0348(4) Uani d . . . 1 . . H H13 1.046586 0.242268 0.551745 0.042 Uiso calc U . R 1 . . C C14 0.96738(13) 0.1537(3) 0.61429(6) 0.0304(4) Uani d . . . 1 . . H H14 1.014906 0.030424 0.623033 0.036 Uiso calc U . R 1 . . C C15 0.87987(12) 0.2068(3) 0.64392(6) 0.0257(3) Uani d . . . 1 . . H H15 0.868677 0.120255 0.672994 0.031 Uiso calc U . R 1 . . C C16 0.66754(12) 0.3031(2) 0.69366(6) 0.0227(3) Uani d . . . 1 . . H H16 0.704441 0.16175 0.69579 0.027 Uiso calc U . R 1 . . C C17 0.57159(12) 0.3235(2) 0.72507(6) 0.0229(3) Uani d . . . 1 . . C C18 0.48227(12) 0.4759(3) 0.71806(6) 0.0254(3) Uani d . . . 1 . . H H18 0.48203 0.577676 0.690764 0.031 Uiso calc U . R 1 . . C C19 0.39514(12) 0.4818(3) 0.74967(6) 0.0253(3) Uani d . . . 1 . . H H19 0.336906 0.588615 0.743924 0.03 Uiso calc U . R 1 . . C C20 0.39060(12) 0.3327(3) 0.79034(6) 0.0238(3) Uani d . . . 1 . . C C21 0.47762(12) 0.1751(3) 0.79653(6) 0.0251(3) Uani d . . . 1 . . H H21 0.476759 0.069542 0.823075 0.03 Uiso calc U . R 1 . . C C22 0.56390(12) 0.1715(3) 0.76472(6) 0.0244(3) Uani d . . . 1 . . H H22 0.62081 0.061356 0.769793 0.029 Uiso calc U . R 1 . . C C23 0.29911(14) 0.1844(3) 0.86331(6) 0.0329(4) Uani d . . . 1 . . H H23A 0.293601 0.030128 0.850544 0.049 Uiso calc U . R 1 . . H H23B 0.233465 0.218331 0.882341 0.049 Uiso calc U . R 1 . . H H23C 0.366926 0.199553 0.885042 0.049 Uiso calc U . R 1 . . C C24 0.21783(13) 0.5103(3) 0.81555(7) 0.0352(4) Uani d . . . 1 . . H H24A 0.252466 0.659719 0.816037 0.053 Uiso calc U . R 1 . . H H24B 0.166518 0.498975 0.84274 0.053 Uiso calc U . R 1 . . H H24C 0.176284 0.487441 0.78356 0.053 Uiso calc U . R 1 . . N N1 0.30403(11) 0.3398(2) 0.82193(5) 0.0303(3) Uani d . . . 1 . . O O1 0.58632(8) 0.70493(17) 0.61814(4) 0.0244(2) Uani d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0278(8) 0.0280(8) 0.0352(9) 0.0025(6) 0.0022(7) 0.0068(7) C2 0.0262(8) 0.0396(10) 0.0459(11) 0.0061(7) -0.0004(7) 0.0164(9) C3 0.0261(8) 0.0503(11) 0.0404(10) -0.0037(8) -0.0079(7) 0.0197(9) C4 0.0348(9) 0.0400(10) 0.0316(9) -0.0084(7) -0.0083(7) 0.0077(8) C5 0.0278(8) 0.0286(8) 0.0268(8) -0.0016(6) -0.0028(6) 0.0046(7) C6 0.0222(7) 0.0246(8) 0.0254(8) 0.0001(6) 0.0008(6) 0.0057(6) C7 0.0247(7) 0.0187(7) 0.0275(8) 0.0005(5) -0.0009(6) 0.0019(6) C8 0.0250(7) 0.0211(7) 0.0249(8) -0.0021(6) -0.0057(6) 0.0000(6) C9 0.0241(7) 0.0224(7) 0.0220(7) -0.0011(6) -0.0071(6) -0.0018(6) C10 0.0231(7) 0.0232(7) 0.0221(7) -0.0038(6) -0.0047(6) -0.0025(6) C11 0.0273(8) 0.0305(9) 0.0267(8) 0.0018(6) -0.0036(6) 0.0037(7) C12 0.0333(9) 0.0430(10) 0.0279(9) 0.0041(7) 0.0035(7) 0.0097(8) C13 0.0279(8) 0.0459(11) 0.0310(9) 0.0050(7) 0.0043(7) 0.0048(8) C14 0.0270(8) 0.0315(9) 0.0321(9) 0.0047(7) -0.0031(7) 0.0014(7) C15 0.0261(7) 0.0247(8) 0.0258(8) -0.0016(6) -0.0025(6) 0.0013(6) C16 0.0235(7) 0.0205(7) 0.0232(7) 0.0007(5) -0.0063(6) -0.0017(6) C17 0.0239(7) 0.0222(7) 0.0223(7) -0.0009(6) -0.0031(6) -0.0015(6) C18 0.0268(7) 0.0229(7) 0.0260(8) 0.0000(6) -0.0045(6) 0.0026(6) C19 0.0234(7) 0.0236(8) 0.0283(8) 0.0035(6) -0.0032(6) 0.0009(6) C20 0.0234(7) 0.0244(8) 0.0229(7) -0.0002(6) -0.0033(6) -0.0017(6) C21 0.0266(7) 0.0249(8) 0.0233(8) 0.0018(6) -0.0050(6) 0.0031(6) C22 0.0246(7) 0.0238(8) 0.0244(8) 0.0036(6) -0.0039(6) 0.0002(6) C23 0.0327(8) 0.0352(9) 0.0312(9) -0.0012(7) 0.0046(7) 0.0035(7) C24 0.0316(8) 0.0379(10) 0.0362(10) 0.0083(7) 0.0033(7) -0.0015(8) N1 0.0275(7) 0.0378(8) 0.0257(7) 0.0070(6) 0.0027(5) 0.0064(6) O1 0.0276(5) 0.0193(5) 0.0253(6) 0.0008(4) -0.0081(4) 0.0014(4) 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' N N 0.0061 0.0033 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . . 120.42(16) ? C2 C1 H1 . . 119.8 ? C6 C1 H1 . . 119.8 ? C3 C2 C1 . . 120.04(16) ? C3 C2 H2 . . 120.0 ? C1 C2 H2 . . 120.0 ? C2 C3 C4 . . 119.89(15) ? C2 C3 H3 . . 120.1 ? C4 C3 H3 . . 120.1 ? C3 C4 C5 . . 120.15(17) ? C3 C4 H4 . . 119.9 ? C5 C4 H4 . . 119.9 ? C6 C5 C4 . . 120.25(15) ? C6 C5 H5 . . 119.9 ? C4 C5 H5 . . 119.9 ? C5 C6 C1 . . 119.24(14) ? C5 C6 C7 . . 121.86(13) ? C1 C6 C7 . . 118.90(14) ? O1 C7 C6 . . 110.25(12) ? O1 C7 H7A . . 109.6 ? C6 C7 H7A . . 109.6 ? O1 C7 H7B . . 109.6 ? C6 C7 H7B . . 109.6 ? H7A C7 H7B . . 108.1 ? O1 C8 C9 . . 109.84(11) ? O1 C8 H8A . . 109.7 ? C9 C8 H8A . . 109.7 ? O1 C8 H8B . . 109.7 ? C9 C8 H8B . . 109.7 ? H8A C8 H8B . . 108.2 ? C16 C9 C10 . . 121.31(14) ? C16 C9 C8 . . 121.80(14) ? C10 C9 C8 . . 116.87(14) ? C11 C10 C15 . . 117.08(15) ? C11 C10 C9 . . 119.63(14) ? C15 C10 C9 . . 123.28(14) ? C12 C11 C10 . . 121.58(15) ? C12 C11 H11 . . 119.2 ? C10 C11 H11 . . 119.2 ? C11 C12 C13 . . 120.44(16) ? C11 C12 H12 . . 119.8 ? C13 C12 H12 . . 119.8 ? C12 C13 C14 . . 119.14(16) ? C12 C13 H13 . . 120.4 ? C14 C13 H13 . . 120.4 ? C15 C14 C13 . . 120.58(15) ? C15 C14 H14 . . 119.7 ? C13 C14 H14 . . 119.7 ? C14 C15 C10 . . 121.17(15) ? C14 C15 H15 . . 119.4 ? C10 C15 H15 . . 119.4 ? C9 C16 C17 . . 131.03(14) ? C9 C16 H16 . . 114.5 ? C17 C16 H16 . . 114.5 ? C22 C17 C18 . . 115.95(14) ? C22 C17 C16 . . 117.87(13) ? C18 C17 C16 . . 126.12(14) ? C19 C18 C17 . . 121.87(14) ? C19 C18 H18 . . 119.1 ? C17 C18 H18 . . 119.1 ? C18 C19 C20 . . 121.40(14) ? C18 C19 H19 . . 119.3 ? C20 C19 H19 . . 119.3 ? N1 C20 C21 . . 121.75(14) ? N1 C20 C19 . . 121.28(13) ? C21 C20 C19 . . 116.97(14) ? C22 C21 C20 . . 120.91(14) ? C22 C21 H21 . . 119.5 ? C20 C21 H21 . . 119.5 ? C21 C22 C17 . . 122.83(14) ? C21 C22 H22 . . 118.6 ? C17 C22 H22 . . 118.6 ? N1 C23 H23A . . 109.5 ? N1 C23 H23B . . 109.5 ? H23A C23 H23B . . 109.5 ? N1 C23 H23C . . 109.5 ? H23A C23 H23C . . 109.5 ? H23B C23 H23C . . 109.5 ? N1 C24 H24A . . 109.5 ? N1 C24 H24B . . 109.5 ? H24A C24 H24B . . 109.5 ? N1 C24 H24C . . 109.5 ? H24A C24 H24C . . 109.5 ? H24B C24 H24C . . 109.5 ? C20 N1 C23 . . 121.03(13) ? C20 N1 C24 . . 120.24(14) ? C23 N1 C24 . . 118.68(14) ? C7 O1 C8 . . 110.76(11) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.390(2) ? C1 C6 . 1.393(2) ? C1 H1 . 0.95 ? C2 C3 . 1.378(3) ? C2 H2 . 0.95 ? C3 C4 . 1.388(3) ? C3 H3 . 0.95 ? C4 C5 . 1.390(2) ? C4 H4 . 0.95 ? C5 C6 . 1.385(2) ? C5 H5 . 0.95 ? C6 C7 . 1.504(2) ? C7 O1 . 1.4215(17) ? C7 H7A . 0.99 ? C7 H7B . 0.99 ? C8 O1 . 1.4349(16) ? C8 C9 . 1.505(2) ? C8 H8A . 0.99 ? C8 H8B . 0.99 ? C9 C16 . 1.347(2) ? C9 C10 . 1.483(2) ? C10 C11 . 1.399(2) ? C10 C15 . 1.406(2) ? C11 C12 . 1.382(2) ? C11 H11 . 0.95 ? C12 C13 . 1.384(2) ? C12 H12 . 0.95 ? C13 C14 . 1.386(2) ? C13 H13 . 0.95 ? C14 C15 . 1.384(2) ? C14 H14 . 0.95 ? C15 H15 . 0.95 ? C16 C17 . 1.464(2) ? C16 H16 . 0.95 ? C17 C22 . 1.403(2) ? C17 C18 . 1.407(2) ? C18 C19 . 1.378(2) ? C18 H18 . 0.95 ? C19 C20 . 1.409(2) ? C19 H19 . 0.95 ? C20 N1 . 1.373(2) ? C20 C21 . 1.405(2) ? C21 C22 . 1.373(2) ? C21 H21 . 0.95 ? C22 H22 . 0.95 ? C23 N1 . 1.448(2) ? C23 H23A . 0.98 ? C23 H23B . 0.98 ? C23 H23C . 0.98 ? C24 N1 . 1.451(2) ? C24 H24A . 0.98 ? C24 H24B . 0.98 ? C24 H24C . 0.98 ?