#------------------------------------------------------------------------------ #$Date: 2020-06-05 13:16:36 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252728 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557871.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_1557871 loop_ _publ_author_name 'Yan, Chenting' 'Takeshita, Masato' 'Nakatsuji, Jun-ya' 'Kurosaki, Akihiro' 'Sato, Kaoko' 'Shang, Rong' 'Nakamoto, Masaaki' 'Yamamoto, Yohsuke' 'Adachi, Yohei' 'Furukawa, Ko' 'Kishi, Ryohei' 'Nakano, Masayoshi' _publ_section_title ; Synthesis and properties of hypervalent electron-rich pentacoordinate nitrogen compounds ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 5082 _journal_paper_doi 10.1039/D0SC00002G _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C26 H25 Cl2 N O4' _chemical_formula_weight 486.37 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-08-05 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.3830(16) _cell_length_b 13.3271(12) _cell_length_c 20.1022(18) _cell_measurement_reflns_used 9952 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.81 _cell_measurement_theta_min 2.22 _cell_volume 4924.9(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0156 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 44338 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.830 _diffrn_reflns_theta_max 24.830 _diffrn_reflns_theta_min 2.026 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_correction_T_min 0.6324 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2032 _refine_diff_density_max 0.452 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 303 _refine_ls_number_reflns 4249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0384 _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^)+(0.0493P)^2^+3.2032P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1025 _refine_ls_wR_factor_ref 0.1076 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3744 _reflns_number_total 4249 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00002g2.cif _cod_data_source_block 2Me_a _cod_depositor_comments 'Adding full bibliography for 1557869--1557876.cif.' _cod_database_code 1557871 _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 0.6324 _shelx_estimated_absorpt_t_max 0.7451 _shelx_res_file ; 20180811_yan_exp389_0ma.res created by SHELXL-2014/7 TITL 20180811_yan_exp389_0ma in Pbca CELL 0.71073 18.3830 13.3271 20.1022 90.000 90.000 90.000 ZERR 8.00 0.0016 0.0012 0.0018 0.000 0.000 0.000 LATT 1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O CL UNIT 208 200 8 32 16 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -100.000 ACTA L.S. 10 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF WGHT 0.049300 3.203200 FVAR 0.09641 CL1 5 0.501014 0.014743 0.093398 11.00000 0.04601 0.08709 = 0.07073 -0.01197 -0.01503 0.03605 CL2 5 0.208476 0.480444 -0.224144 11.00000 0.08146 0.09999 = 0.04879 0.04083 -0.00663 -0.00050 O1 4 0.136292 0.079789 -0.030599 11.00000 0.03336 0.04653 = 0.03885 -0.01506 -0.00305 0.00203 O2 4 0.022505 0.136637 -0.027492 11.00000 0.03677 0.07957 = 0.06495 -0.03078 -0.02240 0.01359 O3 4 0.293177 0.300532 0.198184 11.00000 0.04297 0.07851 = 0.02802 0.00923 -0.00950 -0.02101 O4 4 0.291280 0.374596 0.098725 11.00000 0.02601 0.03610 = 0.03263 0.00424 -0.00192 -0.00320 N1 3 0.230581 0.225101 0.016193 11.00000 0.02334 0.03238 = 0.02444 -0.00006 0.00214 0.00267 C1 1 0.035964 0.278159 0.286530 11.00000 0.05483 0.16604 = 0.05054 -0.03605 0.02676 -0.01746 AFIX 137 H5 2 0.048930 0.349081 0.281506 11.00000 -1.50000 H1 2 0.078918 0.240057 0.300516 11.00000 -1.50000 H6 2 -0.002306 0.271480 0.320180 11.00000 -1.50000 AFIX 0 C2 1 0.008951 0.238151 0.221318 11.00000 0.03256 0.06905 = 0.03439 0.00154 0.00984 -0.00355 C3 1 0.067949 0.238357 0.167375 11.00000 0.02781 0.04154 = 0.03128 0.00254 0.00424 0.00110 C4 1 0.138133 0.273899 0.178069 11.00000 0.03090 0.04058 = 0.02456 -0.00067 0.00265 0.00103 AFIX 43 H14 2 0.150584 0.299193 0.220760 11.00000 -1.20000 AFIX 0 C5 1 0.190756 0.273595 0.128184 11.00000 0.02540 0.03084 = 0.02572 0.00096 -0.00005 0.00113 C6 1 0.175711 0.231579 0.065957 11.00000 0.02403 0.02854 = 0.02395 0.00251 0.00104 0.00328 C7 1 0.295431 0.174393 0.032338 11.00000 0.02496 0.02634 = 0.02613 -0.00610 -0.00025 0.00058 C8 1 0.362497 0.203067 0.006242 11.00000 0.03015 0.03465 = 0.03767 -0.00100 0.00707 0.00043 AFIX 43 H24 2 0.364982 0.257121 -0.024482 11.00000 -1.20000 AFIX 0 C9 1 0.425356 0.153677 0.024611 11.00000 0.02537 0.04699 = 0.05041 -0.00931 0.00632 0.00183 AFIX 43 H25 2 0.470766 0.172604 0.005863 11.00000 -1.20000 AFIX 0 C10 1 0.421867 0.076867 0.070234 11.00000 0.03082 0.04150 = 0.04370 -0.01399 -0.00820 0.01150 C11 1 -0.056549 0.295478 0.197548 11.00000 0.04582 0.18368 = 0.06826 0.02946 0.03122 0.03967 AFIX 137 H3 2 -0.095975 0.288686 0.230052 11.00000 -1.50000 H2 2 -0.072460 0.268595 0.154568 11.00000 -1.50000 H4 2 -0.043895 0.366510 0.192535 11.00000 -1.50000 AFIX 0 C12 1 -0.013830 0.128184 0.233505 11.00000 0.13373 0.10664 = 0.06369 0.00381 0.04961 -0.04572 AFIX 137 H7 2 -0.051883 0.125964 0.267615 11.00000 -1.50000 H9 2 0.028411 0.089517 0.248582 11.00000 -1.50000 H8 2 -0.032479 0.099264 0.192054 11.00000 -1.50000 AFIX 0 C13 1 0.053230 0.200253 0.104449 11.00000 0.02239 0.03813 = 0.03514 0.00315 0.00025 -0.00172 AFIX 43 H13 2 0.005224 0.178159 0.094880 11.00000 -1.20000 AFIX 0 C14 1 0.105757 0.193071 0.054870 11.00000 0.02572 0.03037 = 0.02763 0.00204 -0.00148 0.00253 C15 1 0.083391 0.136484 -0.006083 11.00000 0.02988 0.03526 = 0.03226 0.00008 -0.00329 0.00036 C16 1 0.116657 0.016387 -0.086079 11.00000 0.05351 0.06027 = 0.04946 -0.02721 -0.00513 -0.00061 AFIX 137 H11 2 0.074798 -0.025237 -0.073839 11.00000 -1.50000 H10 2 0.157877 -0.026888 -0.097597 11.00000 -1.50000 H12 2 0.103981 0.058287 -0.124428 11.00000 -1.50000 AFIX 0 C17 1 0.263686 0.315856 0.145953 11.00000 0.02896 0.03380 = 0.02359 -0.00310 0.00235 0.00019 C18 1 0.363842 0.412247 0.110941 11.00000 0.02841 0.04488 = 0.04182 0.00055 0.00091 -0.00833 AFIX 137 H17 2 0.363985 0.452134 0.151896 11.00000 -1.50000 H16 2 0.379152 0.454378 0.073518 11.00000 -1.50000 H15 2 0.397562 0.355743 0.115687 11.00000 -1.50000 AFIX 0 C19 1 0.223088 0.283577 -0.042075 11.00000 0.02569 0.03275 = 0.02341 -0.00070 -0.00049 -0.00199 C20 1 0.190589 0.377447 -0.039111 11.00000 0.03101 0.03407 = 0.03084 -0.00249 0.00249 0.00034 AFIX 43 H21 2 0.172092 0.401307 0.002083 11.00000 -1.20000 AFIX 0 C21 1 0.184781 0.436573 -0.095173 11.00000 0.03501 0.03923 = 0.04390 0.00899 -0.00228 0.00020 AFIX 43 H20 2 0.162024 0.500468 -0.092752 11.00000 -1.20000 AFIX 0 C22 1 0.212278 0.402153 -0.154733 11.00000 0.03985 0.05866 = 0.03274 0.01471 -0.00674 -0.00501 C23 1 0.243690 0.308646 -0.159546 11.00000 0.04439 0.06649 = 0.02233 -0.00201 0.00104 -0.00164 AFIX 43 H19 2 0.262005 0.285387 -0.200959 11.00000 -1.20000 AFIX 0 C24 1 0.248297 0.248797 -0.103275 11.00000 0.04065 0.04195 = 0.02713 -0.00584 0.00185 0.00470 AFIX 43 H18 2 0.268806 0.183544 -0.106460 11.00000 -1.20000 AFIX 0 C25 1 0.293485 0.095949 0.078059 11.00000 0.02925 0.02907 = 0.03890 0.00002 0.00022 -0.00169 AFIX 43 H22 2 0.248173 0.075080 0.096084 11.00000 -1.20000 AFIX 0 C26 1 0.356579 0.048181 0.097492 11.00000 0.04364 0.03108 = 0.03960 -0.00097 -0.00630 0.00643 AFIX 43 H23 2 0.354886 -0.004200 0.129508 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 20180811_yan_exp389_0ma in Pbca REM R1 = 0.0384 for 3744 Fo > 4sig(Fo) and 0.0437 for all 4249 data REM 303 parameters refined using 0 restraints END WGHT 0.0493 3.2032 REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, -y+1, z+1/2 HTAB C18 Cl2_$1 EQIV $2 x-1/2, -y+1/2, -z HTAB C21 Cl1_$2 EQIV $3 x, -y+1/2, z-1/2 HTAB C23 O3_$3 REM Highest difference peak 0.452, deepest hole -0.421, 1-sigma level 0.041 Q1 1 0.0086 0.3652 0.2515 11.00000 0.05 0.45 Q2 1 0.2283 0.4192 -0.2385 11.00000 0.05 0.34 Q3 1 0.0280 0.1798 0.2745 11.00000 0.05 0.29 Q4 1 0.4899 -0.0017 0.1342 11.00000 0.05 0.27 Q5 1 -0.0570 0.1719 0.2034 11.00000 0.05 0.23 ; _shelx_res_checksum 20934 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -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 Cl1 Cl 0.50101(3) 0.01474(5) 0.09340(3) 0.0679(2) Uani 1 1 d . . . . . Cl2 Cl 0.20848(4) 0.48044(6) -0.22414(3) 0.0767(2) Uani 1 1 d . . . . . O1 O 0.13629(7) 0.07979(10) -0.03060(6) 0.0396(3) Uani 1 1 d . . . . . O2 O 0.02251(8) 0.13664(13) -0.02749(8) 0.0604(5) Uani 1 1 d . . . . . O3 O 0.29318(7) 0.30053(12) 0.19818(6) 0.0498(4) Uani 1 1 d . . . . . O4 O 0.29128(6) 0.37460(9) 0.09872(6) 0.0316(3) Uani 1 1 d . . . . . N1 N 0.23058(7) 0.22510(10) 0.01619(6) 0.0267(3) Uani 1 1 d . . . . . C1 C 0.03596(15) 0.2782(3) 0.28653(13) 0.0905(11) Uani 1 1 d . . . . . H5 H 0.0489 0.3491 0.2815 0.136 Uiso 1 1 calc R U . . . H1 H 0.0789 0.2401 0.3005 0.136 Uiso 1 1 calc R U . . . H6 H -0.0023 0.2715 0.3202 0.136 Uiso 1 1 calc R U . . . C2 C 0.00895(10) 0.23815(18) 0.22132(10) 0.0453(5) Uani 1 1 d . . . . . C3 C 0.06795(9) 0.23836(14) 0.16737(9) 0.0335(4) Uani 1 1 d . . . . . C4 C 0.13813(9) 0.27390(13) 0.17807(8) 0.0320(4) Uani 1 1 d . . . . . H14 H 0.1506 0.2992 0.2208 0.038 Uiso 1 1 calc R U . . . C5 C 0.19076(9) 0.27360(12) 0.12818(8) 0.0273(4) Uani 1 1 d . . . . . C6 C 0.17571(9) 0.23158(12) 0.06596(8) 0.0255(3) Uani 1 1 d . . . . . C7 C 0.29543(8) 0.17439(12) 0.03234(8) 0.0258(4) Uani 1 1 d . . . . . C8 C 0.36250(9) 0.20307(14) 0.00624(9) 0.0342(4) Uani 1 1 d . . . . . H24 H 0.3650 0.2571 -0.0245 0.041 Uiso 1 1 calc R U . . . C9 C 0.42536(10) 0.15368(15) 0.02461(10) 0.0409(5) Uani 1 1 d . . . . . H25 H 0.4708 0.1726 0.0059 0.049 Uiso 1 1 calc R U . . . C10 C 0.42187(10) 0.07687(15) 0.07023(9) 0.0387(4) Uani 1 1 d . . . . . C11 C -0.05655(14) 0.2955(3) 0.19755(15) 0.0993(12) Uani 1 1 d . . . . . H3 H -0.0960 0.2887 0.2301 0.149 Uiso 1 1 calc R U . . . H2 H -0.0725 0.2686 0.1546 0.149 Uiso 1 1 calc R U . . . H4 H -0.0439 0.3665 0.1925 0.149 Uiso 1 1 calc R U . . . C12 C -0.0138(2) 0.1282(3) 0.23350(15) 0.1014(12) Uani 1 1 d . . . . . H7 H -0.0519 0.1260 0.2676 0.152 Uiso 1 1 calc R U . . . H9 H 0.0284 0.0895 0.2486 0.152 Uiso 1 1 calc R U . . . H8 H -0.0325 0.0993 0.1921 0.152 Uiso 1 1 calc R U . . . C13 C 0.05323(9) 0.20025(13) 0.10445(8) 0.0319(4) Uani 1 1 d . . . . . H13 H 0.0052 0.1782 0.0949 0.038 Uiso 1 1 calc R U . . . C14 C 0.10576(9) 0.19307(12) 0.05487(8) 0.0279(4) Uani 1 1 d . . . . . C15 C 0.08339(9) 0.13648(13) -0.00608(9) 0.0325(4) Uani 1 1 d . . . . . C16 C 0.11666(13) 0.01639(18) -0.08608(11) 0.0544(6) Uani 1 1 d . . . . . H11 H 0.0748 -0.0252 -0.0738 0.082 Uiso 1 1 calc R U . . . H10 H 0.1579 -0.0269 -0.0976 0.082 Uiso 1 1 calc R U . . . H12 H 0.1040 0.0583 -0.1244 0.082 Uiso 1 1 calc R U . . . C17 C 0.26369(9) 0.31586(13) 0.14595(8) 0.0288(4) Uani 1 1 d . . . . . C18 C 0.36384(9) 0.41225(15) 0.11094(9) 0.0384(4) Uani 1 1 d . . . . . H17 H 0.3640 0.4521 0.1519 0.058 Uiso 1 1 calc R U . . . H16 H 0.3792 0.4544 0.0735 0.058 Uiso 1 1 calc R U . . . H15 H 0.3976 0.3557 0.1157 0.058 Uiso 1 1 calc R U . . . C19 C 0.22309(9) 0.28358(12) -0.04208(8) 0.0273(4) Uani 1 1 d . . . . . C20 C 0.19059(9) 0.37745(13) -0.03911(9) 0.0320(4) Uani 1 1 d . . . . . H21 H 0.1721 0.4013 0.0021 0.038 Uiso 1 1 calc R U . . . C21 C 0.18478(10) 0.43657(15) -0.09517(9) 0.0394(4) Uani 1 1 d . . . . . H20 H 0.1620 0.5005 -0.0928 0.047 Uiso 1 1 calc R U . . . C22 C 0.21228(11) 0.40215(17) -0.15473(9) 0.0438(5) Uani 1 1 d . . . . . C23 C 0.24369(11) 0.30865(17) -0.15955(9) 0.0444(5) Uani 1 1 d . . . . . H19 H 0.2620 0.2854 -0.2010 0.053 Uiso 1 1 calc R U . . . C24 C 0.24830(10) 0.24880(15) -0.10328(8) 0.0366(4) Uani 1 1 d . . . . . H18 H 0.2688 0.1835 -0.1065 0.044 Uiso 1 1 calc R U . . . C25 C 0.29348(9) 0.09595(13) 0.07806(9) 0.0324(4) Uani 1 1 d . . . . . H22 H 0.2482 0.0751 0.0961 0.039 Uiso 1 1 calc R U . . . C26 C 0.35658(10) 0.04818(14) 0.09749(9) 0.0381(4) Uani 1 1 d . . . . . H23 H 0.3549 -0.0042 0.1295 0.046 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 Cl1 0.0460(3) 0.0871(5) 0.0707(4) -0.0120(3) -0.0150(3) 0.0361(3) Cl2 0.0815(5) 0.1000(5) 0.0488(4) 0.0408(3) -0.0066(3) -0.0005(4) O1 0.0334(7) 0.0465(7) 0.0389(7) -0.0151(6) -0.0030(5) 0.0020(6) O2 0.0368(8) 0.0796(11) 0.0649(10) -0.0308(9) -0.0224(7) 0.0136(8) O3 0.0430(8) 0.0785(10) 0.0280(7) 0.0092(7) -0.0095(6) -0.0210(7) O4 0.0260(6) 0.0361(7) 0.0326(6) 0.0042(5) -0.0019(5) -0.0032(5) N1 0.0233(7) 0.0324(8) 0.0244(7) -0.0001(6) 0.0021(5) 0.0027(6) C1 0.0548(15) 0.166(3) 0.0505(14) -0.0361(18) 0.0268(12) -0.0175(18) C2 0.0326(10) 0.0690(14) 0.0344(10) 0.0015(9) 0.0098(8) -0.0035(9) C3 0.0278(9) 0.0415(10) 0.0313(9) 0.0025(8) 0.0042(7) 0.0011(7) C4 0.0309(9) 0.0406(10) 0.0246(8) -0.0007(7) 0.0027(7) 0.0010(7) C5 0.0254(8) 0.0308(9) 0.0257(8) 0.0010(7) 0.0000(6) 0.0011(7) C6 0.0240(8) 0.0285(8) 0.0240(8) 0.0025(6) 0.0010(6) 0.0033(6) C7 0.0250(8) 0.0263(8) 0.0261(8) -0.0061(6) -0.0003(6) 0.0006(6) C8 0.0301(9) 0.0346(9) 0.0377(9) -0.0010(8) 0.0071(7) 0.0004(7) C9 0.0254(9) 0.0470(11) 0.0504(11) -0.0093(9) 0.0063(8) 0.0018(8) C10 0.0308(9) 0.0415(10) 0.0437(10) -0.0140(9) -0.0082(8) 0.0115(8) C11 0.0458(14) 0.184(4) 0.0683(18) 0.029(2) 0.0312(13) 0.0397(19) C12 0.134(3) 0.107(2) 0.0637(18) 0.0038(17) 0.0496(19) -0.046(2) C13 0.0224(8) 0.0381(9) 0.0351(9) 0.0032(7) 0.0002(7) -0.0017(7) C14 0.0257(8) 0.0304(8) 0.0276(8) 0.0020(7) -0.0015(7) 0.0025(7) C15 0.0299(9) 0.0353(9) 0.0323(9) 0.0001(7) -0.0033(7) 0.0004(7) C16 0.0535(13) 0.0603(14) 0.0495(12) -0.0272(11) -0.0051(10) -0.0006(11) C17 0.0290(9) 0.0338(9) 0.0236(8) -0.0031(7) 0.0024(7) 0.0002(7) C18 0.0284(9) 0.0449(11) 0.0418(10) 0.0005(8) 0.0009(8) -0.0083(8) C19 0.0257(8) 0.0328(9) 0.0234(8) -0.0007(7) -0.0005(6) -0.0020(7) C20 0.0310(9) 0.0341(9) 0.0308(9) -0.0025(7) 0.0025(7) 0.0003(7) C21 0.0350(10) 0.0392(10) 0.0439(11) 0.0090(8) -0.0023(8) 0.0002(8) C22 0.0399(11) 0.0587(13) 0.0327(10) 0.0147(9) -0.0067(8) -0.0050(9) C23 0.0444(11) 0.0665(13) 0.0223(9) -0.0020(9) 0.0010(8) -0.0016(10) C24 0.0407(10) 0.0419(10) 0.0271(9) -0.0058(7) 0.0019(8) 0.0047(9) C25 0.0293(9) 0.0291(9) 0.0389(10) 0.0000(7) 0.0002(7) -0.0017(7) C26 0.0436(11) 0.0311(9) 0.0396(10) -0.0010(8) -0.0063(8) 0.0064(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 C16 115.89(15) . . ? C17 O4 C18 115.75(13) . . ? C7 N1 C19 122.55(13) . . ? C7 N1 C6 117.84(13) . . ? C19 N1 C6 118.68(13) . . ? C2 C1 H5 109.5 . . ? C2 C1 H1 109.5 . . ? H5 C1 H1 109.5 . . ? C2 C1 H6 109.5 . . ? H5 C1 H6 109.5 . . ? H1 C1 H6 109.5 . . ? C1 C2 C11 111.2(2) . . ? C1 C2 C3 112.53(17) . . ? C11 C2 C3 109.91(17) . . ? C1 C2 C12 106.8(2) . . ? C11 C2 C12 108.4(3) . . ? C3 C2 C12 107.80(19) . . ? C13 C3 C4 116.47(15) . . ? C13 C3 C2 120.35(16) . . ? C4 C3 C2 123.18(16) . . ? C3 C4 C5 122.12(16) . . ? C3 C4 H14 118.9 . . ? C5 C4 H14 118.9 . . ? C4 C5 C6 120.51(15) . . ? C4 C5 C17 116.67(14) . . ? C6 C5 C17 122.76(14) . . ? C5 C6 C14 118.04(14) . . ? C5 C6 N1 120.86(14) . . ? C14 C6 N1 121.06(14) . . ? C25 C7 C8 118.50(15) . . ? C25 C7 N1 119.38(14) . . ? C8 C7 N1 122.05(15) . . ? C9 C8 C7 120.62(17) . . ? C9 C8 H24 119.7 . . ? C7 C8 H24 119.7 . . ? C10 C9 C8 119.61(17) . . ? C10 C9 H25 120.2 . . ? C8 C9 H25 120.2 . . ? C26 C10 C9 120.91(16) . . ? C26 C10 Cl1 119.48(16) . . ? C9 C10 Cl1 119.61(15) . . ? C2 C11 H3 109.5 . . ? C2 C11 H2 109.5 . . ? H3 C11 H2 109.5 . . ? C2 C11 H4 109.5 . . ? H3 C11 H4 109.5 . . ? H2 C11 H4 109.5 . . ? C2 C12 H7 109.5 . . ? C2 C12 H9 109.5 . . ? H7 C12 H9 109.5 . . ? C2 C12 H8 109.5 . . ? H7 C12 H8 109.5 . . ? H9 C12 H8 109.5 . . ? C3 C13 C14 122.83(16) . . ? C3 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C13 C14 C6 119.83(15) . . ? C13 C14 C15 115.51(15) . . ? C6 C14 C15 124.51(15) . . ? O2 C15 O1 123.50(17) . . ? O2 C15 C14 123.33(16) . . ? O1 C15 C14 112.95(14) . . ? O1 C16 H11 109.5 . . ? O1 C16 H10 109.5 . . ? H11 C16 H10 109.5 . . ? O1 C16 H12 109.5 . . ? H11 C16 H12 109.5 . . ? H10 C16 H12 109.5 . . ? O3 C17 O4 123.53(16) . . ? O3 C17 C5 123.34(15) . . ? O4 C17 C5 113.10(14) . . ? O4 C18 H17 109.5 . . ? O4 C18 H16 109.5 . . ? H17 C18 H16 109.5 . . ? O4 C18 H15 109.5 . . ? H17 C18 H15 109.5 . . ? H16 C18 H15 109.5 . . ? C20 C19 C24 118.74(16) . . ? C20 C19 N1 120.22(14) . . ? C24 C19 N1 121.04(15) . . ? C21 C20 C19 120.88(16) . . ? C21 C20 H21 119.6 . . ? C19 C20 H21 119.6 . . ? C22 C21 C20 119.42(18) . . ? C22 C21 H20 120.3 . . ? C20 C21 H20 120.3 . . ? C23 C22 C21 121.07(17) . . ? C23 C22 Cl2 120.14(15) . . ? C21 C22 Cl2 118.77(16) . . ? C22 C23 C24 119.27(17) . . ? C22 C23 H19 120.4 . . ? C24 C23 H19 120.4 . . ? C23 C24 C19 120.56(18) . . ? C23 C24 H18 119.7 . . ? C19 C24 H18 119.7 . . ? C26 C25 C7 120.78(16) . . ? C26 C25 H22 119.6 . . ? C7 C25 H22 119.6 . . ? C10 C26 C25 119.55(17) . . ? C10 C26 H23 120.2 . . ? C25 C26 H23 120.2 . . ? 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 Cl1 C10 1.7376(18) . ? Cl2 C22 1.7437(19) . ? O1 C15 1.326(2) . ? O1 C16 1.445(2) . ? O2 C15 1.199(2) . ? O3 C17 1.199(2) . ? O4 C17 1.331(2) . ? O4 C18 1.446(2) . ? N1 C7 1.408(2) . ? N1 C19 1.414(2) . ? N1 C6 1.423(2) . ? C1 C2 1.500(3) . ? C1 H5 0.9800 . ? C1 H1 0.9800 . ? C1 H6 0.9800 . ? C2 C11 1.504(3) . ? C2 C3 1.534(2) . ? C2 C12 1.544(4) . ? C3 C13 1.390(2) . ? C3 C4 1.391(2) . ? C4 C5 1.393(2) . ? C4 H14 0.9500 . ? C5 C6 1.398(2) . ? C5 C17 1.497(2) . ? C6 C14 1.402(2) . ? C7 C25 1.392(2) . ? C7 C8 1.393(2) . ? C8 C9 1.380(3) . ? C8 H24 0.9500 . ? C9 C10 1.376(3) . ? C9 H25 0.9500 . ? C10 C26 1.374(3) . ? C11 H3 0.9800 . ? C11 H2 0.9800 . ? C11 H4 0.9800 . ? C12 H7 0.9800 . ? C12 H9 0.9800 . ? C12 H8 0.9800 . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 C15 1.496(2) . ? C16 H11 0.9800 . ? C16 H10 0.9800 . ? C16 H12 0.9800 . ? C18 H17 0.9800 . ? C18 H16 0.9800 . ? C18 H15 0.9800 . ? C19 C20 1.388(2) . ? C19 C24 1.394(2) . ? C20 C21 1.379(3) . ? C20 H21 0.9500 . ? C21 C22 1.378(3) . ? C21 H20 0.9500 . ? C22 C23 1.377(3) . ? C23 C24 1.387(3) . ? C23 H19 0.9500 . ? C24 H18 0.9500 . ? C25 C26 1.380(2) . ? C25 H22 0.9500 . ? C26 H23 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 C1 C2 C3 C13 177.6(2) . . . . ? C11 C2 C3 C13 -57.9(3) . . . . ? C12 C2 C3 C13 60.1(3) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C11 C2 C3 C4 123.3(3) . . . . ? C12 C2 C3 C4 -118.7(2) . . . . ? C13 C3 C4 C5 1.3(3) . . . . ? C2 C3 C4 C5 -179.79(18) . . . . ? C3 C4 C5 C6 -3.8(3) . . . . ? C3 C4 C5 C17 178.84(16) . . . . ? C4 C5 C6 C14 2.0(2) . . . . ? C17 C5 C6 C14 179.25(15) . . . . ? C4 C5 C6 N1 -175.90(15) . . . . ? C17 C5 C6 N1 1.3(2) . . . . ? C7 N1 C6 C5 56.3(2) . . . . ? C19 N1 C6 C5 -112.95(17) . . . . ? C7 N1 C6 C14 -121.54(17) . . . . ? C19 N1 C6 C14 69.2(2) . . . . ? C19 N1 C7 C25 -160.97(15) . . . . ? C6 N1 C7 C25 30.2(2) . . . . ? C19 N1 C7 C8 22.0(2) . . . . ? C6 N1 C7 C8 -146.82(16) . . . . ? C25 C7 C8 C9 1.0(3) . . . . ? N1 C7 C8 C9 178.05(16) . . . . ? C7 C8 C9 C10 -1.4(3) . . . . ? C8 C9 C10 C26 0.4(3) . . . . ? C8 C9 C10 Cl1 -179.96(14) . . . . ? C4 C3 C13 C14 2.8(3) . . . . ? C2 C3 C13 C14 -176.10(17) . . . . ? C3 C13 C14 C6 -4.5(3) . . . . ? C3 C13 C14 C15 171.25(16) . . . . ? C5 C6 C14 C13 2.0(2) . . . . ? N1 C6 C14 C13 179.87(15) . . . . ? C5 C6 C14 C15 -173.39(15) . . . . ? N1 C6 C14 C15 4.5(2) . . . . ? C16 O1 C15 O2 0.1(3) . . . . ? C16 O1 C15 C14 174.84(16) . . . . ? C13 C14 C15 O2 33.7(3) . . . . ? C6 C14 C15 O2 -150.80(19) . . . . ? C13 C14 C15 O1 -141.06(16) . . . . ? C6 C14 C15 O1 34.5(2) . . . . ? C18 O4 C17 O3 6.0(2) . . . . ? C18 O4 C17 C5 -175.94(14) . . . . ? C4 C5 C17 O3 41.1(2) . . . . ? C6 C5 C17 O3 -136.21(19) . . . . ? C4 C5 C17 O4 -136.90(16) . . . . ? C6 C5 C17 O4 45.8(2) . . . . ? C7 N1 C19 C20 -135.15(17) . . . . ? C6 N1 C19 C20 33.6(2) . . . . ? C7 N1 C19 C24 44.5(2) . . . . ? C6 N1 C19 C24 -146.75(16) . . . . ? C24 C19 C20 C21 -1.6(3) . . . . ? N1 C19 C20 C21 178.12(16) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? C20 C21 C22 C23 1.8(3) . . . . ? C20 C21 C22 Cl2 -176.87(14) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? Cl2 C22 C23 C24 177.93(15) . . . . ? C22 C23 C24 C19 -1.6(3) . . . . ? C20 C19 C24 C23 2.7(3) . . . . ? N1 C19 C24 C23 -177.02(16) . . . . ? C8 C7 C25 C26 0.5(3) . . . . ? N1 C7 C25 C26 -176.65(15) . . . . ? C9 C10 C26 C25 1.1(3) . . . . ? Cl1 C10 C26 C25 -178.58(14) . . . . ? C7 C25 C26 C10 -1.5(3) . . . . ?