#------------------------------------------------------------------------------ #$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $ #$Revision: 176453 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/82/7218266.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_7218266 loop_ _publ_author_name 'Zhong, Yuan' 'Ma, Shixiong' 'Xu, Zhaoqing' 'Chang, Min' 'Wang, Rui' _publ_section_title ; Organocatalytic asymmetric vinylogous Michael addition of 3-alkylidene oxindoles to \a-substituted \b-nitroacrylates: Facile construction of chiral all-carbon quaternary center ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C4RA09128K _journal_year 2014 _chemical_formula_moiety 'C21 H19 Cl N2 O5, 0.25(C H2 Cl2)' _chemical_formula_sum 'C21.25 H19.5 Cl1.5 N2 O5' _chemical_formula_weight 436.06 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2014-06-10 _audit_creation_method ; Olex2 1.2 (compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846) ; _cell_angle_alpha 90 _cell_angle_beta 100.764(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.3843(3) _cell_length_b 9.8961(3) _cell_length_c 28.9183(7) _cell_measurement_reflns_used 4403 _cell_measurement_temperature 292.1(6) _cell_measurement_theta_max 69.8060 _cell_measurement_theta_min 4.6510 _cell_volume 4044.05(18) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 292.1(6) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_details ; 1 omega -28.00 17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 38.0000 30.0000 45 2 omega -74.00 -36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 60.0000 38 3 omega 23.00 72.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 38.0000 30.0000 49 4 omega -61.00 -36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -120.0000 25 5 omega -110.00 -84.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -42.5000 178.0000 -180.0000 26 6 omega 44.00 79.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 150.0000 35 7 omega 32.00 125.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -60.0000 93 8 omega 100.00 125.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 151.0000 65.0000 25 9 omega 37.00 63.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -180.0000 26 10 omega 27.00 122.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 38.0000 90.0000 95 11 omega 77.00 103.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -180.0000 26 12 omega 23.00 109.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 56.0000 -125.0000 150.0000 86 13 omega 73.00 99.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -77.0000 0.0000 26 14 omega 50.00 102.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -30.0000 52 15 omega 42.00 114.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -150.0000 72 16 omega 60.00 93.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -38.0000 120.0000 33 17 omega 107.00 133.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 38.0000 -60.0000 26 18 omega 44.00 94.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -25.0000 -60.0000 50 19 omega 46.00 86.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -50.0000 -150.0000 40 20 omega 48.00 87.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -38.0000 -90.0000 39 21 omega 63.00 91.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -25.0000 -30.0000 28 22 omega 126.00 177.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 0.0000 51 23 omega 42.00 91.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -38.0000 90.0000 49 24 omega 96.00 173.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 50.0000 90.0000 77 25 omega 97.00 177.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 122.0000 -96.0000 80 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0649506000 _diffrn_orient_matrix_UB_12 0.1130793000 _diffrn_orient_matrix_UB_13 -0.0243135000 _diffrn_orient_matrix_UB_21 0.0601454000 _diffrn_orient_matrix_UB_22 0.1058671000 _diffrn_orient_matrix_UB_23 0.0312927000 _diffrn_orient_matrix_UB_31 0.0635953000 _diffrn_orient_matrix_UB_32 0.0152933000 _diffrn_orient_matrix_UB_33 -0.0370440000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_unetI/netI 0.0521 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 9128 _diffrn_reflns_point_group_measured_fraction_full 0.817 _diffrn_reflns_point_group_measured_fraction_max 0.797 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.571 _diffrn_reflns_theta_min 4.670 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.601 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.432 _exptl_crystal_description block _exptl_crystal_F_000 1812 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.222 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details ; Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.006(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 549 _refine_ls_number_reflns 6189 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0488 _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^)+(0.0800P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1259 _refine_ls_wR_factor_ref 0.1305 _reflns_Friedel_coverage 0.530 _reflns_Friedel_fraction_full 0.613 _reflns_Friedel_fraction_max 0.588 _reflns_number_gt 5805 _reflns_number_total 6189 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4ra09128k2.cif _cod_data_source_block zhangyuan0608 _cod_original_cell_volume 4044.06(17) _cod_original_formula_sum 'C21.25 H19.50 Cl1.50 N2 O5' _cod_database_code 7218266 #BEGIN Tags that were not found in dictionaries: _shelxl_version_number 2013-2 _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. ; _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: H45A(0.5) H45B(0.5) 3.a Secondary CH2 refined with riding coordinates: C19(H19A,H19B), C32(H32A,H32B), C41(H41A,H41B), C45(H45A,H45B) 3.b Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17), N3(H3A), C24(H24), C25(H25), C26(H26), C27(H27), C35(H35), C36(H36), C38(H38), C39(H39) 3.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C40(H40A,H40B,H40C), C44(H44A,H44B, H44C) ; _shelx_res_file ; TITL zhangyuan0608 in C2 #5 CELL 1.54184 14.384339 9.896117 28.918314 90 100.7643 90 ZERR 8 0.000333 0.000253 0.000669 0 0.0023 0 LATT -7 SYMM -X,+Y,-Z SFAC C H N O Cl UNIT 170 156 16 40 12 L.S. 10 PLAN 20 REM reset to Cl2 #5 BOND $H HTAB MORE -1 CONF fmap 2 acta SHEL 999 0.81 REM D:/olex2_zhangyuan0608/zhangyuan0608.hkl WGHT 0.080000 FVAR 2.88156 CL1 5 0.568484 0.166777 -0.054201 11.00000 0.07697 0.08974 = 0.03947 -0.00996 0.00142 -0.01728 O1 4 0.665538 0.480419 0.207016 11.00000 0.03040 0.06334 = 0.04206 -0.00459 0.00479 -0.00620 O2 4 0.703296 0.194618 0.231609 11.00000 0.09573 0.06955 = 0.06344 0.01886 0.04915 0.01367 O3 4 0.633929 0.219776 0.159791 11.00000 0.04231 0.07896 = 0.07958 -0.00060 0.02154 -0.01156 O4 4 0.956124 0.327341 0.103048 11.00000 0.05779 0.04525 = 0.06109 -0.00135 0.03274 -0.00635 O5 4 0.937433 0.124114 0.133713 11.00000 0.04111 0.04435 = 0.05548 0.00932 0.01254 0.00668 N1 3 0.727251 0.546897 0.281885 11.00000 0.03339 0.05214 = 0.04094 -0.00310 0.01298 -0.00343 AFIX 43 H1 2 0.674530 0.555025 0.291580 11.00000 -1.20000 AFIX 0 N2 3 0.704615 0.205040 0.189949 11.00000 0.06015 0.03553 = 0.05987 0.00504 0.03136 -0.00424 C1 1 0.815414 0.570974 0.309780 11.00000 0.03965 0.03018 = 0.03737 0.00182 0.00734 -0.00115 C2 1 0.835459 0.606780 0.356632 11.00000 0.05804 0.04193 = 0.04259 -0.00057 0.01395 -0.00115 AFIX 43 H2 2 0.787270 0.619890 0.373593 11.00000 -1.20000 AFIX 0 C3 1 0.929630 0.622694 0.377749 11.00000 0.07461 0.04562 = 0.03742 -0.00592 -0.00639 -0.00137 AFIX 43 H3 2 0.945306 0.646772 0.409333 11.00000 -1.20000 AFIX 0 C4 1 1.000283 0.602804 0.351900 11.00000 0.04781 0.04645 = 0.05141 -0.00469 -0.01120 -0.00518 AFIX 43 H4 2 1.063113 0.613795 0.366538 11.00000 -1.20000 AFIX 0 C5 1 0.979927 0.567004 0.304864 11.00000 0.03801 0.03973 = 0.05041 -0.00174 0.00217 -0.00284 AFIX 43 H5 2 1.028484 0.554249 0.288110 11.00000 -1.20000 AFIX 0 C6 1 0.885805 0.550245 0.282835 11.00000 0.03395 0.02594 = 0.03851 0.00273 0.00470 -0.00315 C7 1 0.837850 0.508787 0.235113 11.00000 0.03128 0.02736 = 0.03801 0.00200 0.00592 -0.00209 C8 1 0.734223 0.509085 0.237588 11.00000 0.02992 0.03600 = 0.03717 0.00257 0.00638 -0.00212 C9 1 0.874099 0.477198 0.196927 11.00000 0.03359 0.02795 = 0.04219 0.00298 0.01137 -0.00208 C10 1 0.813070 0.437573 0.150289 11.00000 0.03687 0.03323 = 0.03556 0.00084 0.01025 0.00000 H10A 2 0.748641 0.468919 0.150183 11.00000 0.03625 H10B 2 0.835552 0.495502 0.124981 11.00000 0.03423 C11 1 0.815332 0.286265 0.135732 11.00000 0.03756 0.02971 = 0.03494 0.00101 0.00930 -0.00220 C12 1 0.747643 0.258610 0.088385 11.00000 0.03593 0.03710 = 0.03805 0.00135 0.01020 -0.00191 C13 1 0.701881 0.361029 0.060267 11.00000 0.06082 0.03585 = 0.04414 -0.00160 0.00400 0.00210 AFIX 43 H13 2 0.707894 0.449707 0.071058 11.00000 -1.20000 AFIX 0 C14 1 0.647425 0.334237 0.016479 11.00000 0.06792 0.05142 = 0.04403 0.00592 0.00171 0.00200 AFIX 43 H14 2 0.617569 0.404185 -0.002056 11.00000 -1.20000 AFIX 0 C15 1 0.638008 0.202809 0.000711 11.00000 0.04994 0.05682 = 0.03753 -0.00393 0.00871 -0.00948 C16 1 0.681952 0.098423 0.027794 11.00000 0.05219 0.04316 = 0.05269 -0.01113 0.00889 -0.00820 AFIX 43 H16 2 0.675442 0.009862 0.016911 11.00000 -1.20000 AFIX 0 C17 1 0.735854 0.127343 0.071383 11.00000 0.04755 0.03562 = 0.05227 -0.00313 0.00265 -0.00548 AFIX 43 H17 2 0.765085 0.056880 0.089870 11.00000 -1.20000 AFIX 0 C18 1 0.978550 0.486223 0.197311 11.00000 0.03573 0.06130 = 0.05106 -0.00949 0.01479 -0.00818 AFIX 137 H18A 2 1.009840 0.409412 0.213534 11.00000 -1.50000 H18B 2 1.003211 0.567541 0.213109 11.00000 -1.50000 H18C 2 0.989311 0.487481 0.165536 11.00000 -1.50000 AFIX 0 C19 1 0.799398 0.190419 0.175410 11.00000 0.04648 0.03604 = 0.04089 0.00492 0.01426 -0.00510 AFIX 23 H19A 2 0.805938 0.098051 0.165258 11.00000 -1.20000 H19B 2 0.848658 0.206321 0.202703 11.00000 -1.20000 AFIX 0 C21 1 0.912398 0.250955 0.122904 11.00000 0.03868 0.03844 = 0.03344 0.00043 0.00669 -0.00212 C22 1 1.017532 0.071760 0.115429 11.00000 0.04738 0.05408 = 0.06474 0.00314 0.01656 0.01120 AFIX 137 H22A 2 1.010983 0.095285 0.082774 11.00000 -1.50000 H22B 2 1.019709 -0.024785 0.118688 11.00000 -1.50000 H22C 2 1.074928 0.110124 0.132721 11.00000 -1.50000 AFIX 0 CL2 5 0.608242 0.262458 0.491752 11.00000 0.05693 0.08175 = 0.09240 -0.02562 0.04334 -0.00632 O6 4 1.062643 -0.067182 0.309240 11.00000 0.02850 0.06243 = 0.04418 -0.00350 0.00614 -0.00757 O7 4 1.075212 0.224882 0.340798 11.00000 0.03922 0.08100 = 0.07044 0.00236 0.01651 -0.01500 O8 4 0.984010 0.219759 0.272859 11.00000 0.07656 0.06914 = 0.04768 0.00917 0.02598 0.00356 O9 4 1.062536 0.102268 0.438083 11.00000 0.04606 0.04435 = 0.06105 0.00249 -0.01237 0.00574 O10 4 1.006857 0.313371 0.426492 11.00000 0.04363 0.03724 = 0.05700 -0.00394 -0.00801 -0.00521 N3 3 0.992639 -0.131352 0.235358 11.00000 0.03238 0.05254 = 0.04170 -0.00445 0.01296 -0.00502 AFIX 43 H3A 2 1.043489 -0.142761 0.224216 11.00000 -1.20000 AFIX 0 N4 3 0.997103 0.224460 0.315565 11.00000 0.04875 0.03782 = 0.04840 0.00727 0.01812 -0.00534 C23 1 0.901137 -0.150705 0.209175 11.00000 0.03837 0.03088 = 0.04044 0.00186 0.00521 -0.00433 C24 1 0.876882 -0.187739 0.163013 11.00000 0.06107 0.03895 = 0.04097 -0.00183 0.01378 -0.00289 AFIX 43 H24 2 0.922644 -0.205611 0.144976 11.00000 -1.20000 AFIX 0 C25 1 0.780766 -0.197623 0.144081 11.00000 0.06706 0.03960 = 0.04207 -0.00178 -0.00436 -0.00395 AFIX 43 H25 2 0.761717 -0.221272 0.112611 11.00000 -1.20000 AFIX 0 C26 1 0.713735 -0.173050 0.171086 11.00000 0.04460 0.04670 = 0.05880 -0.00666 -0.00824 -0.00532 AFIX 43 H26 2 0.649959 -0.179830 0.157572 11.00000 -1.20000 AFIX 0 C27 1 0.739471 -0.138137 0.218371 11.00000 0.03639 0.03990 = 0.05026 -0.00488 0.00226 -0.00246 AFIX 43 H27 2 0.693451 -0.122704 0.236471 11.00000 -1.20000 AFIX 0 C28 1 0.835322 -0.126613 0.238247 11.00000 0.03322 0.02713 = 0.03987 0.00136 0.00672 -0.00210 C29 1 0.888532 -0.086336 0.285009 11.00000 0.02869 0.02698 = 0.04068 0.00025 0.00896 -0.00284 C30 1 0.991643 -0.092557 0.280289 11.00000 0.03144 0.03759 = 0.03642 0.00220 0.00967 -0.00159 C31 1 0.857472 -0.052035 0.324489 11.00000 0.02900 0.02783 = 0.04586 0.00112 0.01037 -0.00336 C32 1 0.924274 -0.008283 0.368794 11.00000 0.03199 0.03089 = 0.03473 -0.00016 0.00764 0.00086 AFIX 23 H32A 2 0.988625 -0.027390 0.365100 11.00000 -1.20000 H32B 2 0.911507 -0.062228 0.394910 11.00000 -1.20000 AFIX 0 C33 1 0.917341 0.143491 0.381444 11.00000 0.02908 0.02849 = 0.03435 0.00219 0.00505 -0.00154 C34 1 0.833346 0.173619 0.406376 11.00000 0.03191 0.02667 = 0.03396 -0.00260 0.00418 -0.00472 C35 1 0.765025 0.270454 0.391449 11.00000 0.03767 0.03516 = 0.05150 0.00634 0.00885 -0.00007 AFIX 43 H35 2 0.765637 0.317562 0.363680 11.00000 -1.20000 AFIX 0 C36 1 0.694796 0.298181 0.417870 11.00000 0.03352 0.04093 = 0.07313 -0.00179 0.00917 0.00395 AFIX 43 H36 2 0.648888 0.363391 0.407860 11.00000 -1.20000 AFIX 0 C37 1 0.694903 0.228410 0.458229 11.00000 0.03589 0.04823 = 0.05580 -0.01804 0.01813 -0.00740 C38 1 0.760843 0.129716 0.473786 11.00000 0.04488 0.05473 = 0.03774 -0.00336 0.01253 -0.01208 AFIX 43 H38 2 0.758565 0.081526 0.501161 11.00000 -1.20000 AFIX 0 C39 1 0.830708 0.103646 0.447802 11.00000 0.03591 0.04092 = 0.03729 0.00430 0.00491 0.00422 AFIX 43 H39 2 0.876411 0.038482 0.458228 11.00000 -1.20000 AFIX 0 C40 1 0.754163 -0.053742 0.327133 11.00000 0.03226 0.05487 = 0.05452 -0.01591 0.01484 -0.00881 AFIX 137 H40A 2 0.723286 0.022338 0.310245 11.00000 -1.50000 H40B 2 0.747187 -0.048853 0.359464 11.00000 -1.50000 H40C 2 0.725999 -0.135803 0.313380 11.00000 -1.50000 AFIX 0 C41 1 0.911631 0.235677 0.338249 11.00000 0.03447 0.03229 = 0.03870 0.00483 0.00664 -0.00389 AFIX 23 H41A 2 0.855695 0.212373 0.315322 11.00000 -1.20000 H41B 2 0.904962 0.328645 0.347746 11.00000 -1.20000 AFIX 0 C43 1 1.006108 0.181046 0.418384 11.00000 0.03424 0.03385 = 0.03943 0.00054 0.00368 -0.00331 C44 1 1.089006 0.365440 0.457552 11.00000 0.05979 0.05579 = 0.07799 -0.00749 -0.01899 -0.01716 AFIX 137 H44A 2 1.145127 0.334344 0.447380 11.00000 -1.50000 H44B 2 1.089223 0.334286 0.489010 11.00000 -1.50000 H44C 2 1.087453 0.462414 0.456979 11.00000 -1.50000 AFIX 0 CL3 5 0.603516 -0.279237 0.010402 11.00000 0.07105 0.07860 = 0.08538 0.00797 0.02584 0.00906 C45 1 0.500000 -0.180723 0.000000 10.50000 0.06710 0.05203 = 0.05795 0.00000 0.02556 0.00000 AFIX 23 H45A 2 0.500860 -0.122988 -0.027023 10.50000 -1.20000 H45B 2 0.499140 -0.122985 0.027023 10.50000 -1.20000 AFIX 0 HKLF 4 REM zhangyuan0608 in C2 #5 REM R1 = 0.0488 for 5805 Fo > 4sig(Fo) and 0.0513 for all 6189 data REM 549 parameters refined using 1 restraints END WGHT 0.0800 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x-1/2, y+1/2, z HTAB N1 O6_$1 HTAB C19 O8 EQIV $2 x+1/2, y+1/2, z HTAB C22 Cl3_$2 EQIV $3 x+1/2, y-1/2, z HTAB C22 O1_$3 HTAB N3 O1_$3 EQIV $4 -x+3/2, y-1/2, -z HTAB C24 Cl1_$4 HTAB C45 O4_$4 EQIV $5 x-1/2, y-1/2, z HTAB C45 O4_$5 REM Highest difference peak 0.222, deepest hole -0.308, 1-sigma level 0.056 Q1 1 0.5395 0.2403 0.0100 11.00000 0.05 0.22 Q2 1 0.5047 -0.1930 0.0383 11.00000 0.05 0.22 Q3 1 0.4447 0.1470 -0.0972 11.00000 0.05 0.20 Q4 1 1.1419 -0.1203 0.2621 11.00000 0.05 0.20 Q5 1 0.6764 -0.2602 -0.0391 11.00000 0.05 0.19 Q6 1 0.5724 0.2023 0.0507 11.00000 0.05 0.19 Q7 1 1.0532 0.2378 0.0739 11.00000 0.05 0.19 Q8 1 0.9985 0.1142 0.0327 11.00000 0.05 0.18 Q9 1 0.5366 0.0557 0.0327 11.00000 0.05 0.18 Q10 1 1.0460 0.5912 0.4567 11.00000 0.05 0.18 Q11 1 0.9649 0.7712 0.4518 11.00000 0.05 0.18 Q12 1 0.6173 0.2619 0.0093 11.00000 0.05 0.18 Q13 1 0.5156 -0.2302 0.0481 11.00000 0.05 0.18 Q14 1 0.8752 0.5517 0.2603 11.00000 0.05 0.18 Q15 1 0.9011 0.7131 0.2764 11.00000 0.05 0.17 Q16 1 1.0096 0.1873 0.0490 11.00000 0.05 0.17 Q17 1 0.7220 0.1950 0.4670 11.00000 0.05 0.17 Q18 1 1.0593 0.4074 0.3400 11.00000 0.05 0.17 Q19 1 0.5760 0.5390 0.2508 11.00000 0.05 0.17 Q20 1 0.8199 0.0523 0.0808 11.00000 0.05 0.17 ; _shelx_res_checksum 62408 _olex2_submission_special_instructions 'No special instructions were received' #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy Cl1 Cl 0.56848(10) 0.16678(17) -0.05420(4) 0.0699(4) Uani 1 1 d . . . O1 O 0.66554(17) 0.4804(4) 0.20702(9) 0.0455(7) Uani 1 1 d . . . O2 O 0.7033(3) 0.1946(4) 0.23161(13) 0.0718(11) Uani 1 1 d . . . O3 O 0.6339(2) 0.2198(4) 0.15979(13) 0.0656(10) Uani 1 1 d . . . O4 O 0.9561(2) 0.3273(3) 0.10305(11) 0.0519(7) Uani 1 1 d . . . O5 O 0.9374(2) 0.1241(3) 0.13371(10) 0.0465(7) Uani 1 1 d . . . N1 N 0.7273(2) 0.5469(4) 0.28189(11) 0.0414(7) Uani 1 1 d . . . H1 H 0.6745 0.5550 0.2916 0.050 Uiso 1 1 calc R . . N2 N 0.7046(3) 0.2050(4) 0.18995(13) 0.0493(9) Uani 1 1 d . . . C1 C 0.8154(3) 0.5710(4) 0.30978(13) 0.0357(7) Uani 1 1 d . . . C2 C 0.8355(3) 0.6068(5) 0.35663(14) 0.0469(9) Uani 1 1 d . . . H2 H 0.7873 0.6199 0.3736 0.056 Uiso 1 1 calc R . . C3 C 0.9296(4) 0.6227(5) 0.37775(14) 0.0547(11) Uani 1 1 d . . . H3 H 0.9453 0.6468 0.4093 0.066 Uiso 1 1 calc R . . C4 C 1.0003(3) 0.6028(5) 0.35190(15) 0.0512(10) Uani 1 1 d . . . H4 H 1.0631 0.6138 0.3665 0.061 Uiso 1 1 calc R . . C5 C 0.9799(3) 0.5670(5) 0.30486(15) 0.0435(9) Uani 1 1 d . . . H5 H 1.0285 0.5542 0.2881 0.052 Uiso 1 1 calc R . . C6 C 0.8858(2) 0.5502(4) 0.28283(13) 0.0331(7) Uani 1 1 d . . . C7 C 0.8378(2) 0.5088(4) 0.23511(12) 0.0323(7) Uani 1 1 d . . . C8 C 0.7342(2) 0.5091(4) 0.23759(13) 0.0344(7) Uani 1 1 d . . . C9 C 0.8741(2) 0.4772(4) 0.19693(13) 0.0340(7) Uani 1 1 d . . . C10 C 0.8131(2) 0.4376(4) 0.15029(12) 0.0348(7) Uani 1 1 d . . . H10A H 0.749(3) 0.469(5) 0.1502(14) 0.036(11) Uiso 1 1 d . . . H10B H 0.836(3) 0.496(5) 0.1250(15) 0.034(10) Uiso 1 1 d . . . C11 C 0.8153(2) 0.2863(4) 0.13573(12) 0.0337(7) Uani 1 1 d . . . C12 C 0.7476(2) 0.2586(4) 0.08838(12) 0.0366(7) Uani 1 1 d . . . C13 C 0.7019(3) 0.3610(5) 0.06027(15) 0.0477(9) Uani 1 1 d . . . H13 H 0.7079 0.4497 0.0711 0.057 Uiso 1 1 calc R . . C14 C 0.6474(4) 0.3342(5) 0.01648(16) 0.0556(11) Uani 1 1 d . . . H14 H 0.6176 0.4042 -0.0021 0.067 Uiso 1 1 calc R . . C15 C 0.6380(3) 0.2028(5) 0.00071(14) 0.0480(10) Uani 1 1 d . . . C16 C 0.6820(3) 0.0984(5) 0.02779(15) 0.0495(10) Uani 1 1 d . . . H16 H 0.6754 0.0099 0.0169 0.059 Uiso 1 1 calc R . . C17 C 0.7359(3) 0.1273(5) 0.07138(15) 0.0460(9) Uani 1 1 d . . . H17 H 0.7651 0.0569 0.0899 0.055 Uiso 1 1 calc R . . C18 C 0.9786(3) 0.4862(5) 0.19731(15) 0.0485(10) Uani 1 1 d . . . H18A H 1.0098 0.4094 0.2135 0.073 Uiso 1 1 calc GR . . H18B H 1.0032 0.5675 0.2131 0.073 Uiso 1 1 calc GR . . H18C H 0.9893 0.4875 0.1655 0.073 Uiso 1 1 calc GR . . C19 C 0.7994(3) 0.1904(4) 0.17541(13) 0.0404(8) Uani 1 1 d . . . H19A H 0.8059 0.0981 0.1653 0.048 Uiso 1 1 calc R . . H19B H 0.8487 0.2063 0.2027 0.048 Uiso 1 1 calc R . . C21 C 0.9124(3) 0.2510(4) 0.12290(12) 0.0369(8) Uani 1 1 d . . . C22 C 1.0175(3) 0.0718(6) 0.11543(17) 0.0546(11) Uani 1 1 d . . . H22A H 1.0110 0.0953 0.0828 0.082 Uiso 1 1 calc GR . . H22B H 1.0197 -0.0248 0.1187 0.082 Uiso 1 1 calc GR . . H22C H 1.0749 0.1101 0.1327 0.082 Uiso 1 1 calc GR . . Cl2 Cl 0.60824(9) 0.26246(16) 0.49175(5) 0.0732(4) Uani 1 1 d . . . O6 O 1.06264(17) -0.0672(4) 0.30924(9) 0.0451(7) Uani 1 1 d . . . O7 O 1.0752(2) 0.2249(4) 0.34080(12) 0.0627(9) Uani 1 1 d . . . O8 O 0.9840(3) 0.2198(4) 0.27286(11) 0.0626(9) Uani 1 1 d . . . O9 O 1.0625(2) 0.1023(3) 0.43808(11) 0.0534(8) Uani 1 1 d . . . O10 O 1.0069(2) 0.3134(3) 0.42649(11) 0.0482(7) Uani 1 1 d . . . N3 N 0.9926(2) -0.1314(4) 0.23536(11) 0.0414(7) Uani 1 1 d . . . H3A H 1.0435 -0.1428 0.2242 0.050 Uiso 1 1 calc R . . N4 N 0.9971(2) 0.2245(4) 0.31557(12) 0.0438(7) Uani 1 1 d . . . C23 C 0.9011(3) -0.1507(4) 0.20917(13) 0.0368(8) Uani 1 1 d . . . C24 C 0.8769(3) -0.1877(5) 0.16301(14) 0.0464(9) Uani 1 1 d . . . H24 H 0.9226 -0.2056 0.1450 0.056 Uiso 1 1 calc R . . C25 C 0.7808(3) -0.1976(5) 0.14408(15) 0.0515(10) Uani 1 1 d . . . H25 H 0.7617 -0.2213 0.1126 0.062 Uiso 1 1 calc R . . C26 C 0.7137(3) -0.1731(5) 0.17109(17) 0.0523(10) Uani 1 1 d . . . H26 H 0.6500 -0.1798 0.1576 0.063 Uiso 1 1 calc R . . C27 C 0.7395(3) -0.1381(4) 0.21837(15) 0.0429(8) Uani 1 1 d . . . H27 H 0.6935 -0.1227 0.2365 0.052 Uiso 1 1 calc R . . C28 C 0.8353(2) -0.1266(4) 0.23825(13) 0.0334(7) Uani 1 1 d . . . C29 C 0.8885(2) -0.0863(4) 0.28501(12) 0.0318(7) Uani 1 1 d . . . C30 C 0.9916(2) -0.0926(4) 0.28029(13) 0.0347(7) Uani 1 1 d . . . C31 C 0.8575(2) -0.0520(4) 0.32449(13) 0.0338(7) Uani 1 1 d . . . C32 C 0.9243(2) -0.0083(4) 0.36879(12) 0.0324(7) Uani 1 1 d . . . H32A H 0.9886 -0.0274 0.3651 0.039 Uiso 1 1 calc R . . H32B H 0.9115 -0.0622 0.3949 0.039 Uiso 1 1 calc R . . C33 C 0.9173(2) 0.1435(4) 0.38144(11) 0.0308(7) Uani 1 1 d . . . C34 C 0.8333(2) 0.1736(4) 0.40638(11) 0.0311(7) Uani 1 1 d . . . C35 C 0.7650(3) 0.2705(4) 0.39145(14) 0.0414(8) Uani 1 1 d . . . H35 H 0.7656 0.3176 0.3637 0.050 Uiso 1 1 calc R . . C36 C 0.6948(3) 0.2982(5) 0.41787(17) 0.0493(10) Uani 1 1 d . . . H36 H 0.6489 0.3634 0.4079 0.059 Uiso 1 1 calc R . . C37 C 0.6949(3) 0.2284(5) 0.45823(15) 0.0454(9) Uani 1 1 d . . . C38 C 0.7608(3) 0.1297(5) 0.47379(13) 0.0452(9) Uani 1 1 d . . . H38 H 0.7586 0.0815 0.5012 0.054 Uiso 1 1 calc R . . C39 C 0.8307(3) 0.1036(4) 0.44780(12) 0.0383(8) Uani 1 1 d . . . H39 H 0.8764 0.0385 0.4582 0.046 Uiso 1 1 calc R . . C40 C 0.7542(3) -0.0537(5) 0.32713(15) 0.0463(10) Uani 1 1 d . . . H40A H 0.7233 0.0223 0.3102 0.070 Uiso 1 1 calc GR . . H40B H 0.7472 -0.0489 0.3595 0.070 Uiso 1 1 calc GR . . H40C H 0.7260 -0.1358 0.3134 0.070 Uiso 1 1 calc GR . . C41 C 0.9116(2) 0.2357(4) 0.33825(12) 0.0352(7) Uani 1 1 d . . . H41A H 0.8557 0.2124 0.3153 0.042 Uiso 1 1 calc R . . H41B H 0.9050 0.3286 0.3477 0.042 Uiso 1 1 calc R . . C43 C 1.0061(2) 0.1810(4) 0.41838(13) 0.0363(7) Uani 1 1 d . . . C44 C 1.0890(4) 0.3654(6) 0.4576(2) 0.0686(15) Uani 1 1 d . . . H44A H 1.1451 0.3343 0.4474 0.103 Uiso 1 1 calc GR . . H44B H 1.0892 0.3343 0.4890 0.103 Uiso 1 1 calc GR . . H44C H 1.0875 0.4624 0.4570 0.103 Uiso 1 1 calc GR . . Cl3 Cl 0.60352(11) -0.27924(18) 0.01040(6) 0.0769(4) Uani 1 1 d . . . C45 C 0.5000 -0.1807(8) 0.0000 0.0572(16) Uani 1 2 d S T P H45A H 0.5009 -0.1230 -0.0270 0.069 Uiso 0.5 1 calc R . . H45B H 0.4991 -0.1230 0.0270 0.069 Uiso 0.5 1 calc R . . 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 0.0770(7) 0.0897(10) 0.0395(5) -0.0100(6) 0.0014(5) -0.0173(7) O1 0.0304(12) 0.0633(19) 0.0421(13) -0.0046(14) 0.0048(10) -0.0062(13) O2 0.096(3) 0.070(3) 0.0634(19) 0.0189(19) 0.049(2) 0.014(2) O3 0.0423(15) 0.079(3) 0.080(2) -0.001(2) 0.0215(15) -0.0116(17) O4 0.0578(17) 0.0452(17) 0.0611(17) -0.0014(14) 0.0327(14) -0.0063(14) O5 0.0411(14) 0.0444(17) 0.0555(16) 0.0093(13) 0.0125(12) 0.0067(12) N1 0.0334(14) 0.052(2) 0.0409(16) -0.0031(15) 0.0130(12) -0.0034(14) N2 0.060(2) 0.0355(19) 0.060(2) 0.0050(16) 0.0314(17) -0.0042(16) C1 0.0397(18) 0.0302(18) 0.0374(17) 0.0018(14) 0.0073(14) -0.0011(15) C2 0.058(2) 0.042(2) 0.0426(19) -0.0006(18) 0.0139(17) -0.0012(18) C3 0.075(3) 0.046(2) 0.0374(18) -0.0059(18) -0.0064(18) -0.001(2) C4 0.048(2) 0.046(3) 0.051(2) -0.005(2) -0.0112(17) -0.0052(19) C5 0.0380(19) 0.040(2) 0.050(2) -0.0017(18) 0.0022(15) -0.0028(17) C6 0.0340(17) 0.0259(17) 0.0385(17) 0.0027(14) 0.0047(13) -0.0031(13) C7 0.0313(16) 0.0274(17) 0.0380(17) 0.0020(14) 0.0059(13) -0.0021(13) C8 0.0299(15) 0.0360(19) 0.0372(17) 0.0026(14) 0.0064(13) -0.0021(14) C9 0.0336(16) 0.0280(17) 0.0422(17) 0.0030(15) 0.0114(13) -0.0021(14) C10 0.0369(17) 0.0332(19) 0.0356(16) 0.0008(15) 0.0103(14) 0.0000(14) C11 0.0376(17) 0.0297(18) 0.0349(16) 0.0010(14) 0.0093(13) -0.0022(14) C12 0.0359(16) 0.037(2) 0.0380(17) 0.0014(16) 0.0102(13) -0.0019(15) C13 0.061(2) 0.036(2) 0.044(2) -0.0016(17) 0.0040(18) 0.0021(18) C14 0.068(3) 0.051(3) 0.044(2) 0.006(2) 0.0017(19) 0.002(2) C15 0.050(2) 0.057(3) 0.0375(17) -0.0039(18) 0.0087(15) -0.009(2) C16 0.052(2) 0.043(3) 0.053(2) -0.0111(19) 0.0089(18) -0.0082(18) C17 0.048(2) 0.036(2) 0.052(2) -0.0031(18) 0.0026(16) -0.0055(17) C18 0.0357(18) 0.061(3) 0.051(2) -0.009(2) 0.0148(15) -0.0082(19) C19 0.0465(19) 0.036(2) 0.0409(17) 0.0049(16) 0.0143(14) -0.0051(16) C21 0.0387(17) 0.038(2) 0.0334(15) 0.0004(15) 0.0067(13) -0.0021(16) C22 0.047(2) 0.054(3) 0.065(3) 0.003(2) 0.0166(19) 0.011(2) Cl2 0.0569(6) 0.0818(10) 0.0924(9) -0.0256(8) 0.0433(6) -0.0063(6) O6 0.0285(11) 0.0624(19) 0.0442(13) -0.0035(14) 0.0061(10) -0.0076(12) O7 0.0392(14) 0.081(3) 0.0704(19) 0.0024(19) 0.0165(13) -0.0150(16) O8 0.077(2) 0.069(2) 0.0477(16) 0.0092(16) 0.0260(15) 0.0036(18) O9 0.0461(15) 0.0443(18) 0.0610(17) 0.0025(14) -0.0124(13) 0.0057(13) O10 0.0436(14) 0.0372(16) 0.0570(16) -0.0039(14) -0.0080(12) -0.0052(12) N3 0.0324(14) 0.053(2) 0.0417(16) -0.0045(15) 0.0130(12) -0.0050(14) N4 0.0488(17) 0.0378(18) 0.0484(17) 0.0073(15) 0.0181(14) -0.0053(15) C23 0.0384(18) 0.0309(18) 0.0404(18) 0.0019(15) 0.0052(14) -0.0043(14) C24 0.061(2) 0.039(2) 0.0410(19) -0.0018(17) 0.0138(17) -0.0029(19) C25 0.067(3) 0.040(2) 0.042(2) -0.0018(18) -0.0044(18) -0.004(2) C26 0.045(2) 0.047(3) 0.059(2) -0.007(2) -0.0082(18) -0.0053(19) C27 0.0364(18) 0.040(2) 0.050(2) -0.0049(17) 0.0023(15) -0.0025(16) C28 0.0332(16) 0.0271(17) 0.0399(17) 0.0014(14) 0.0067(13) -0.0021(13) C29 0.0287(15) 0.0270(17) 0.0407(17) 0.0002(13) 0.0090(13) -0.0028(12) C30 0.0314(16) 0.038(2) 0.0364(16) 0.0022(15) 0.0097(13) -0.0016(14) C31 0.0290(15) 0.0278(18) 0.0459(18) 0.0011(15) 0.0104(13) -0.0034(13) C32 0.0320(15) 0.0309(18) 0.0347(16) -0.0002(14) 0.0076(12) 0.0009(14) C33 0.0291(15) 0.0285(18) 0.0343(15) 0.0022(13) 0.0051(12) -0.0015(12) C34 0.0319(15) 0.0267(16) 0.0340(15) -0.0026(14) 0.0042(12) -0.0047(14) C35 0.0377(18) 0.035(2) 0.051(2) 0.0063(17) 0.0089(15) -0.0001(15) C36 0.0335(18) 0.041(2) 0.073(3) -0.002(2) 0.0092(17) 0.0039(17) C37 0.0359(17) 0.048(2) 0.056(2) -0.0180(19) 0.0181(16) -0.0074(17) C38 0.045(2) 0.055(3) 0.0377(17) -0.0034(18) 0.0125(14) -0.0121(19) C39 0.0359(16) 0.041(2) 0.0373(17) 0.0043(16) 0.0049(13) 0.0042(15) C40 0.0323(18) 0.055(3) 0.055(2) -0.016(2) 0.0148(15) -0.0088(17) C41 0.0345(16) 0.0323(18) 0.0387(16) 0.0048(15) 0.0066(13) -0.0039(14) C43 0.0342(16) 0.0339(19) 0.0394(16) 0.0005(16) 0.0037(13) -0.0033(15) C44 0.060(3) 0.056(3) 0.078(3) -0.007(3) -0.019(2) -0.017(2) Cl3 0.0711(7) 0.0786(10) 0.0854(9) 0.0080(8) 0.0258(6) 0.0091(7) C45 0.067(4) 0.052(4) 0.058(3) 0.000 0.026(3) 0.000 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 C21 O5 C22 116.8(3) . . C1 N1 H1 124.0 . . C8 N1 H1 124.0 . . C8 N1 C1 112.0(3) . . O2 N2 O3 123.7(4) . . O2 N2 C19 116.9(4) . . O3 N2 C19 119.3(3) . . N1 C1 C6 109.1(3) . . C2 C1 N1 128.0(4) . . C2 C1 C6 122.9(4) . . C1 C2 H2 121.0 . . C1 C2 C3 118.0(4) . . C3 C2 H2 121.0 . . C2 C3 H3 119.9 . . C4 C3 C2 120.1(4) . . C4 C3 H3 119.9 . . C3 C4 H4 119.1 . . C5 C4 C3 121.7(4) . . C5 C4 H4 119.1 . . C4 C5 H5 120.4 . . C4 C5 C6 119.3(4) . . C6 C5 H5 120.4 . . C1 C6 C7 107.4(3) . . C5 C6 C1 117.9(3) . . C5 C6 C7 134.6(4) . . C6 C7 C8 104.4(3) . . C9 C7 C6 130.2(3) . . C9 C7 C8 125.4(3) . . O1 C8 N1 123.5(3) . . O1 C8 C7 129.4(3) . . N1 C8 C7 107.1(3) . . C7 C9 C10 122.8(3) . . C7 C9 C18 121.4(3) . . C18 C9 C10 115.7(3) . . C9 C10 H10A 108(2) . . C9 C10 H10B 106(2) . . C9 C10 C11 116.8(3) . . H10A C10 H10B 104(3) . . C11 C10 H10A 112(3) . . C11 C10 H10B 109(3) . . C12 C11 C10 111.6(3) . . C12 C11 C21 101.2(3) . . C19 C11 C10 112.2(3) . . C19 C11 C12 113.2(3) . . C19 C11 C21 107.8(3) . . C21 C11 C10 110.3(3) . . C13 C12 C11 122.7(4) . . C13 C12 C17 117.6(4) . . C17 C12 C11 119.6(4) . . C12 C13 H13 119.3 . . C14 C13 C12 121.5(4) . . C14 C13 H13 119.3 . . C13 C14 H14 120.4 . . C15 C14 C13 119.2(4) . . C15 C14 H14 120.4 . . C14 C15 Cl1 119.9(4) . . C14 C15 C16 120.9(4) . . C16 C15 Cl1 119.2(4) . . C15 C16 H16 120.5 . . C15 C16 C17 118.9(4) . . C17 C16 H16 120.5 . . C12 C17 H17 119.1 . . C16 C17 C12 121.9(4) . . C16 C17 H17 119.1 . . C9 C18 H18A 109.5 . . C9 C18 H18B 109.5 . . C9 C18 H18C 109.5 . . H18A C18 H18B 109.5 . . H18A C18 H18C 109.5 . . H18B C18 H18C 109.5 . . N2 C19 C11 114.7(3) . . N2 C19 H19A 108.6 . . N2 C19 H19B 108.6 . . C11 C19 H19A 108.6 . . C11 C19 H19B 108.6 . . H19A C19 H19B 107.6 . . O4 C21 O5 124.5(4) . . O4 C21 C11 123.4(4) . . O5 C21 C11 112.0(3) . . O5 C22 H22A 109.5 . . O5 C22 H22B 109.5 . . O5 C22 H22C 109.5 . . H22A C22 H22B 109.5 . . H22A C22 H22C 109.5 . . H22B C22 H22C 109.5 . . C43 O10 C44 116.2(4) . . C23 N3 H3A 123.9 . . C30 N3 H3A 123.9 . . C30 N3 C23 112.2(3) . . O7 N4 C41 118.4(3) . . O8 N4 O7 124.0(4) . . O8 N4 C41 117.6(3) . . C24 C23 N3 127.4(4) . . C24 C23 C28 123.7(4) . . C28 C23 N3 108.9(3) . . C23 C24 H24 121.4 . . C23 C24 C25 117.2(4) . . C25 C24 H24 121.4 . . C24 C25 H25 119.5 . . C26 C25 C24 121.1(4) . . C26 C25 H25 119.5 . . C25 C26 H26 119.4 . . C25 C26 C27 121.2(4) . . C27 C26 H26 119.4 . . C26 C27 H27 120.5 . . C26 C27 C28 119.1(4) . . C28 C27 H27 120.5 . . C23 C28 C29 107.6(3) . . C27 C28 C23 117.8(4) . . C27 C28 C29 134.5(3) . . C28 C29 C30 104.8(3) . . C31 C29 C28 130.3(3) . . C31 C29 C30 124.9(3) . . O6 C30 N3 123.9(3) . . O6 C30 C29 129.6(3) . . N3 C30 C29 106.4(3) . . C29 C31 C32 122.1(3) . . C29 C31 C40 121.9(3) . . C40 C31 C32 116.0(3) . . C31 C32 H32A 108.6 . . C31 C32 H32B 108.6 . . C31 C32 C33 114.7(3) . . H32A C32 H32B 107.6 . . C33 C32 H32A 108.6 . . C33 C32 H32B 108.6 . . C34 C33 C32 112.7(3) . . C34 C33 C43 104.3(3) . . C41 C33 C32 112.2(3) . . C41 C33 C34 109.7(3) . . C41 C33 C43 109.3(3) . . C43 C33 C32 108.3(3) . . C35 C34 C33 124.0(3) . . C35 C34 C39 118.8(3) . . C39 C34 C33 117.1(3) . . C34 C35 H35 119.7 . . C34 C35 C36 120.5(4) . . C36 C35 H35 119.7 . . C35 C36 H36 120.5 . . C37 C36 C35 119.0(4) . . C37 C36 H36 120.5 . . C36 C37 Cl2 119.5(3) . . C36 C37 C38 122.2(4) . . C38 C37 Cl2 118.3(3) . . C37 C38 H38 120.7 . . C37 C38 C39 118.7(4) . . C39 C38 H38 120.7 . . C34 C39 H39 119.6 . . C38 C39 C34 120.9(4) . . C38 C39 H39 119.6 . . C31 C40 H40A 109.5 . . C31 C40 H40B 109.5 . . C31 C40 H40C 109.5 . . H40A C40 H40B 109.5 . . H40A C40 H40C 109.5 . . H40B C40 H40C 109.5 . . N4 C41 C33 112.8(3) . . N4 C41 H41A 109.0 . . N4 C41 H41B 109.0 . . C33 C41 H41A 109.0 . . C33 C41 H41B 109.0 . . H41A C41 H41B 107.8 . . O9 C43 O10 125.3(4) . . O9 C43 C33 125.0(4) . . O10 C43 C33 109.6(3) . . O10 C44 H44A 109.5 . . O10 C44 H44B 109.5 . . O10 C44 H44C 109.5 . . H44A C44 H44B 109.5 . . H44A C44 H44C 109.5 . . H44B C44 H44C 109.5 . . Cl3 C45 Cl3 112.6(4) . 2_655 Cl3 C45 H45A 109.1 . . Cl3 C45 H45A 109.1 2_655 . Cl3 C45 H45B 109.1 2_655 . Cl3 C45 H45B 109.1 . . H45A C45 H45B 107.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1 C15 1.748(4) . O1 C8 1.230(4) . O2 N2 1.213(5) . O3 N2 1.218(5) . O4 C21 1.197(5) . O5 C21 1.327(5) . O5 C22 1.450(5) . N1 H1 0.8600 . N1 C1 1.391(5) . N1 C8 1.356(5) . N2 C19 1.507(5) . C1 C2 1.378(5) . C1 C6 1.403(5) . C2 H2 0.9300 . C2 C3 1.387(6) . C3 H3 0.9300 . C3 C4 1.384(7) . C4 H4 0.9300 . C4 C5 1.383(6) . C5 H5 0.9300 . C5 C6 1.394(5) . C6 C7 1.481(5) . C7 C8 1.506(4) . C7 C9 1.343(5) . C9 C10 1.517(5) . C9 C18 1.503(5) . C10 H10A 0.98(4) . C10 H10B 1.03(4) . C10 C11 1.557(5) . C11 C12 1.549(5) . C11 C19 1.538(5) . C11 C21 1.550(5) . C12 C13 1.386(6) . C12 C17 1.388(6) . C13 H13 0.9300 . C13 C14 1.384(6) . C14 H14 0.9300 . C14 C15 1.377(7) . C15 C16 1.377(7) . C16 H16 0.9300 . C16 C17 1.381(6) . C17 H17 0.9300 . C18 H18A 0.9600 . C18 H18B 0.9600 . C18 H18C 0.9600 . C19 H19A 0.9700 . C19 H19B 0.9700 . C22 H22A 0.9600 . C22 H22B 0.9600 . C22 H22C 0.9600 . Cl2 C37 1.749(4) . O6 C30 1.220(5) . O7 N4 1.220(5) . O8 N4 1.215(5) . O9 C43 1.191(5) . O10 C43 1.330(5) . O10 C44 1.439(5) . N3 H3A 0.8600 . N3 C23 1.404(5) . N3 C30 1.358(5) . N4 C41 1.502(4) . C23 C24 1.365(6) . C23 C28 1.399(5) . C24 H24 0.9300 . C24 C25 1.392(6) . C25 H25 0.9300 . C25 C26 1.371(7) . C26 H26 0.9300 . C26 C27 1.392(6) . C27 H27 0.9300 . C27 C28 1.396(5) . C28 C29 1.479(5) . C29 C30 1.516(4) . C29 C31 1.345(5) . C31 C32 1.514(5) . C31 C40 1.502(4) . C32 H32A 0.9700 . C32 H32B 0.9700 . C32 C33 1.553(5) . C33 C34 1.547(4) . C33 C41 1.537(5) . C33 C43 1.549(4) . C34 C35 1.383(5) . C34 C39 1.390(5) . C35 H35 0.9300 . C35 C36 1.403(6) . C36 H36 0.9300 . C36 C37 1.356(7) . C37 C38 1.377(7) . C38 H38 0.9300 . C38 C39 1.387(5) . C39 H39 0.9300 . C40 H40A 0.9600 . C40 H40B 0.9600 . C40 H40C 0.9600 . C41 H41A 0.9700 . C41 H41B 0.9700 . C44 H44A 0.9600 . C44 H44B 0.9600 . C44 H44C 0.9600 . Cl3 C45 1.758(5) . C45 Cl3 1.758(5) 2_655 C45 H45A 0.9700 . C45 H45B 0.9700 . 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 Cl1 C15 C16 C17 -179.2(3) O2 N2 C19 C11 -141.8(4) O3 N2 C19 C11 41.7(5) N1 C1 C2 C3 178.5(4) N1 C1 C6 C5 -178.8(4) N1 C1 C6 C7 -0.7(4) C1 N1 C8 O1 178.8(4) C1 N1 C8 C7 -0.6(5) C1 C2 C3 C4 0.0(7) C1 C6 C7 C8 0.4(4) C1 C6 C7 C9 -179.8(4) C2 C1 C6 C5 0.0(6) C2 C1 C6 C7 178.0(4) C2 C3 C4 C5 0.0(8) C3 C4 C5 C6 -0.1(7) C4 C5 C6 C1 0.1(6) C4 C5 C6 C7 -177.3(4) C5 C6 C7 C8 178.0(4) C5 C6 C7 C9 -2.1(7) C6 C1 C2 C3 0.0(7) C6 C7 C8 O1 -179.2(4) C6 C7 C8 N1 0.1(4) C6 C7 C9 C10 -179.5(4) C6 C7 C9 C18 -2.7(6) C7 C9 C10 C11 -108.1(4) C8 N1 C1 C2 -177.9(4) C8 N1 C1 C6 0.9(5) C8 C7 C9 C10 0.3(6) C8 C7 C9 C18 177.1(4) C9 C7 C8 O1 1.0(7) C9 C7 C8 N1 -179.8(4) C9 C10 C11 C12 178.1(3) C9 C10 C11 C19 49.9(4) C9 C10 C11 C21 -70.3(4) C10 C11 C12 C13 8.2(5) C10 C11 C12 C17 -175.9(3) C10 C11 C19 N2 62.3(4) C10 C11 C21 O4 -36.6(5) C10 C11 C21 O5 147.6(3) C11 C12 C13 C14 175.1(4) C11 C12 C17 C16 -175.1(3) C12 C11 C19 N2 -65.0(4) C12 C11 C21 O4 81.6(4) C12 C11 C21 O5 -94.2(3) C12 C13 C14 C15 0.5(7) C13 C12 C17 C16 1.0(6) C13 C14 C15 Cl1 179.3(4) C13 C14 C15 C16 -0.1(7) C14 C15 C16 C17 0.2(7) C15 C16 C17 C12 -0.6(6) C17 C12 C13 C14 -0.9(6) C18 C9 C10 C11 75.0(4) C19 C11 C12 C13 135.8(4) C19 C11 C12 C17 -48.2(5) C19 C11 C21 O4 -159.4(4) C19 C11 C21 O5 24.8(4) C21 C11 C12 C13 -109.1(4) C21 C11 C12 C17 66.8(4) C21 C11 C19 N2 -176.1(3) C22 O5 C21 O4 -7.1(6) C22 O5 C21 C11 168.7(3) Cl2 C37 C38 C39 -179.0(3) O7 N4 C41 C33 -45.1(5) O8 N4 C41 C33 137.1(4) N3 C23 C24 C25 -178.5(4) N3 C23 C28 C27 178.8(4) N3 C23 C28 C29 1.6(4) C23 N3 C30 O6 -178.4(4) C23 N3 C30 C29 0.6(5) C23 C24 C25 C26 -1.0(7) C23 C28 C29 C30 -1.2(4) C23 C28 C29 C31 179.5(4) C24 C23 C28 C27 -1.6(6) C24 C23 C28 C29 -178.8(4) C24 C25 C26 C27 -0.4(8) C25 C26 C27 C28 0.8(7) C26 C27 C28 C23 0.2(6) C26 C27 C28 C29 176.5(4) C27 C28 C29 C30 -177.7(4) C27 C28 C29 C31 2.9(7) C28 C23 C24 C25 2.0(6) C28 C29 C30 O6 179.3(4) C28 C29 C30 N3 0.4(4) C28 C29 C31 C32 -177.6(4) C28 C29 C31 C40 1.9(6) C29 C31 C32 C33 110.4(4) C30 N3 C23 C24 179.0(4) C30 N3 C23 C28 -1.4(5) C30 C29 C31 C32 3.2(6) C30 C29 C31 C40 -177.4(4) C31 C29 C30 O6 -1.3(7) C31 C29 C30 N3 179.8(4) C31 C32 C33 C34 80.5(3) C31 C32 C33 C41 -44.0(4) C31 C32 C33 C43 -164.7(3) C32 C33 C34 C35 -126.4(4) C32 C33 C34 C39 57.5(4) C32 C33 C41 N4 -60.9(4) C32 C33 C43 O9 -9.3(5) C32 C33 C43 O10 173.9(3) C33 C34 C35 C36 -175.5(4) C33 C34 C39 C38 176.5(3) C34 C33 C41 N4 173.0(3) C34 C33 C43 O9 110.9(4) C34 C33 C43 O10 -65.8(4) C34 C35 C36 C37 -0.1(7) C35 C34 C39 C38 0.2(6) C35 C36 C37 Cl2 179.6(3) C35 C36 C37 C38 -1.0(7) C36 C37 C38 C39 1.7(7) C37 C38 C39 C34 -1.2(6) C39 C34 C35 C36 0.5(6) C40 C31 C32 C33 -69.1(4) C41 C33 C34 C35 -0.6(5) C41 C33 C34 C39 -176.6(3) C41 C33 C43 O9 -131.9(4) C41 C33 C43 O10 51.4(4) C43 C33 C34 C35 116.4(4) C43 C33 C34 C39 -59.7(4) C43 C33 C41 N4 59.2(4) C44 O10 C43 O9 7.8(7) C44 O10 C43 C33 -175.5(4)