#------------------------------------------------------------------------------ #$Date: 2020-05-07 02:11:17 +0300 (Thu, 07 May 2020) $ #$Revision: 251841 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157494.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_7157494 loop_ _publ_author_name 'Ravindran, Jaice' 'Yadhukrishnan, Velickakathu' 'Asha , Reghuvaran' 'Lankalapalli, Ravi Shankar' _publ_section_title ; Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00721H _journal_year 2020 _chemical_formula_moiety 'C33 H30 Cl N3 O9' _chemical_formula_sum 'C33 H30 Cl N3 O9' _chemical_formula_weight 648.05 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-12-12 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 102.592(3) _cell_angle_beta 95.138(4) _cell_angle_gamma 101.978(3) _cell_formula_units_Z 2 _cell_length_a 9.3935(6) _cell_length_b 10.3136(7) _cell_length_c 17.8351(12) _cell_measurement_reflns_used 9858 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.07 _cell_measurement_theta_min 3.01 _cell_volume 1633.08(19) _computing_cell_refinement 'APEX3/SAINT (Bruker, 2016)' _computing_data_collection 'APEX3(Bruker, 2016)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2016)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker axs kappa apex3 CMOS Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 46502 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 3.018 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2016)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.318 _exptl_crystal_description block _exptl_crystal_F_000 676 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.349 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.068 _refine_ls_extinction_coef 0.032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 420 _refine_ls_number_reflns 5738 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0498 _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^)+(0.0729P)^2^+0.4651P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1267 _refine_ls_wR_factor_ref 0.1504 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4161 _reflns_number_total 5738 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00721h2.cif _cod_data_source_block JR637 _cod_database_code 7157494 _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 0.974 _shelx_estimated_absorpt_t_max 0.983 _shelx_res_file ; JR637.res created by SHELXL-2014/7 TITL jr637_a.res in P-1 CELL 0.71073 9.3935 10.3136 17.8351 102.592 95.138 101.978 ZERR 2.00 0.0006 0.0007 0.0012 0.003 0.004 0.003 LATT 1 SFAC C H N O CL UNIT 66 60 6 18 2 MERG 2 OMIT -3.00 50.00 OMIT -1 1 1 HTAB C2 O1 HTAB C3 O1 EQIV $1 x-1, y, z HTAB C19 O7_$1 EQIV $2 x, y+1, z HTAB C23 O9_$2 EQIV $3 x+1, y, z HTAB C32 O4_$3 HTAB N1 O3 FMAP 2 PLAN 20 SIZE 0.10 0.10 0.15 ACTA BOND $H CONF L.S. 4 TEMP 23.00 WGHT 0.072900 0.465100 EXTI 0.031878 FVAR 0.82186 C1 1 0.238592 0.157313 0.357762 11.00000 0.14747 0.32517 = 0.05507 -0.01469 0.00377 0.13867 AFIX 33 H1A 2 0.181290 0.128815 0.307184 11.00000 -1.50000 H1B 2 0.323902 0.227162 0.357754 11.00000 -1.50000 H1C 2 0.268720 0.080590 0.370793 11.00000 -1.50000 AFIX 0 C2 1 0.012895 0.109147 0.418873 11.00000 0.15390 0.17881 = 0.08216 0.00160 -0.01280 -0.02803 AFIX 33 H2A 2 -0.047268 0.081877 0.369108 11.00000 -1.50000 H2B 2 0.040071 0.030879 0.431471 11.00000 -1.50000 H2C 2 -0.041132 0.147950 0.457610 11.00000 -1.50000 AFIX 0 C3 1 0.099867 0.333918 0.397303 11.00000 0.20717 0.17572 = 0.08775 0.05615 -0.00960 0.08693 AFIX 33 H3A 2 0.039579 0.305858 0.347559 11.00000 -1.50000 H3B 2 0.044629 0.370042 0.436212 11.00000 -1.50000 H3C 2 0.184924 0.403042 0.395966 11.00000 -1.50000 AFIX 0 C4 1 0.147761 0.212577 0.416438 11.00000 0.07357 0.11038 = 0.04533 0.01432 0.00446 0.04416 C5 1 0.208506 0.315601 0.560167 11.00000 0.05574 0.05491 = 0.05066 0.01601 0.00910 0.02174 C6 1 0.335831 0.352529 0.628064 11.00000 0.04903 0.04288 = 0.04877 0.01289 0.01193 0.01300 AFIX 13 H6 2 0.421134 0.410319 0.614174 11.00000 -1.20000 AFIX 0 C7 1 0.381182 0.229272 0.646800 11.00000 0.04697 0.04237 = 0.05493 0.00926 0.00348 0.01385 C8 1 0.313595 0.172011 0.698223 11.00000 0.05443 0.03812 = 0.06226 0.01394 0.00312 0.01553 AFIX 43 H8 2 0.335116 0.092245 0.707282 11.00000 -1.20000 AFIX 0 C9 1 0.208676 0.229508 0.740060 11.00000 0.05022 0.03966 = 0.05797 0.01633 0.00698 0.01161 C10 1 0.210257 0.364430 0.743489 11.00000 0.04408 0.04200 = 0.04541 0.01439 0.00393 0.00987 C11 1 0.112375 0.150539 0.783167 11.00000 0.06483 0.04095 = 0.06683 0.01746 0.01025 0.00764 C12 1 0.083026 -0.036509 0.841645 11.00000 0.11822 0.07471 = 0.10070 0.05791 0.01130 0.00359 AFIX 33 H12A 2 0.130389 -0.108112 0.848191 11.00000 -1.50000 H12B 2 0.078777 0.019622 0.891600 11.00000 -1.50000 H12C 2 -0.014879 -0.075843 0.814763 11.00000 -1.50000 AFIX 0 C13 1 0.502492 0.178248 0.613921 11.00000 0.06391 0.06150 = 0.06593 0.01381 0.01396 0.02493 C14 1 0.693514 0.217262 0.537514 11.00000 0.10116 0.13925 = 0.14628 0.05105 0.07472 0.06108 AFIX 33 H14A 2 0.728063 0.274917 0.504156 11.00000 -1.50000 H14B 2 0.768667 0.230704 0.580507 11.00000 -1.50000 H14C 2 0.670210 0.123419 0.508919 11.00000 -1.50000 AFIX 0 C15 1 0.132263 0.448921 0.795769 11.00000 0.04587 0.03850 = 0.04831 0.01470 0.00867 0.00752 C16 1 0.155626 0.469294 0.875416 11.00000 0.05152 0.06085 = 0.05349 0.02081 0.00778 0.01168 AFIX 43 H16 2 0.219921 0.426256 0.897697 11.00000 -1.20000 AFIX 0 C17 1 0.085208 0.552327 0.922338 11.00000 0.06027 0.06568 = 0.04902 0.01022 0.01340 0.00323 AFIX 43 H17 2 0.102178 0.566018 0.975974 11.00000 -1.20000 AFIX 0 C18 1 -0.010557 0.614825 0.888980 11.00000 0.06027 0.04303 = 0.06894 0.00684 0.02478 0.00505 C19 1 -0.037285 0.595084 0.809763 11.00000 0.05374 0.04424 = 0.07226 0.01880 0.01443 0.01496 AFIX 43 H19 2 -0.103610 0.636561 0.787777 11.00000 -1.20000 AFIX 0 C20 1 0.035080 0.513368 0.763379 11.00000 0.05275 0.04434 = 0.05181 0.01446 0.00653 0.01208 AFIX 43 H20 2 0.018861 0.501087 0.709820 11.00000 -1.20000 AFIX 0 C21 1 0.351978 0.575116 0.719563 11.00000 0.05289 0.03661 = 0.05114 0.01344 0.01478 0.01186 C22 1 0.454451 0.632623 0.784524 11.00000 0.05635 0.04701 = 0.05298 0.01347 0.01290 0.01111 C23 1 0.516618 0.771211 0.805558 11.00000 0.07723 0.05362 = 0.06810 0.00039 0.01227 0.00162 AFIX 43 H23 2 0.585316 0.809386 0.849928 11.00000 -1.20000 AFIX 0 C24 1 0.474608 0.852030 0.759284 11.00000 0.10157 0.03708 = 0.09725 0.01304 0.02937 0.00667 AFIX 43 H24 2 0.514764 0.945717 0.772940 11.00000 -1.20000 AFIX 0 C25 1 0.375150 0.796051 0.693968 11.00000 0.09732 0.04461 = 0.08605 0.02729 0.02304 0.02202 AFIX 43 H25 2 0.349086 0.851400 0.662882 11.00000 -1.20000 AFIX 0 C26 1 0.312786 0.657589 0.673634 11.00000 0.07020 0.04882 = 0.06569 0.02245 0.01451 0.01989 AFIX 43 H26 2 0.244469 0.619799 0.629083 11.00000 -1.20000 AFIX 0 C27 1 0.582543 0.467097 0.803858 11.00000 0.04432 0.06215 = 0.05500 0.01032 0.00217 0.00696 C28 1 0.604914 0.372292 0.853450 11.00000 0.04582 0.05956 = 0.05077 0.00876 0.00156 0.00817 C29 1 0.532326 0.363932 0.916777 11.00000 0.06631 0.08971 = 0.06123 0.02304 0.01267 0.03598 AFIX 43 H29 2 0.468085 0.420045 0.929875 11.00000 -1.20000 AFIX 0 C30 1 0.553909 0.273201 0.960984 11.00000 0.07160 0.10072 = 0.05974 0.02883 0.01886 0.03497 AFIX 43 H30 2 0.505323 0.267501 1.003771 11.00000 -1.20000 AFIX 0 C31 1 0.649007 0.191944 0.939872 11.00000 0.05366 0.06352 = 0.05613 0.01429 -0.00035 0.01153 C32 1 0.723279 0.198780 0.878247 11.00000 0.05855 0.06300 = 0.07155 0.01294 0.01198 0.01798 AFIX 43 H32 2 0.787904 0.142819 0.865745 11.00000 -1.20000 AFIX 0 C33 1 0.701257 0.290451 0.834288 11.00000 0.05885 0.06756 = 0.06419 0.01713 0.01731 0.01615 AFIX 43 H33 2 0.751390 0.296555 0.792058 11.00000 -1.20000 AFIX 0 N1 3 0.240143 0.254573 0.492522 11.00000 0.06427 0.11175 = 0.04743 0.01041 0.00579 0.04785 N2 3 0.293055 0.430438 0.697749 11.00000 0.05075 0.03582 = 0.04784 0.01207 0.00947 0.01095 N3 3 0.675720 0.096394 0.987696 11.00000 0.07199 0.07783 = 0.07108 0.02179 0.00424 0.02150 O1 4 0.091174 0.342702 0.569777 11.00000 0.06909 0.13674 = 0.06411 0.00108 0.00219 0.05442 O2 4 0.544428 0.081893 0.626782 11.00000 0.10593 0.09591 = 0.14314 0.05858 0.05598 0.06983 O3 4 0.562356 0.251790 0.566298 11.00000 0.07412 0.08258 = 0.08281 0.02640 0.03416 0.03632 O4 4 -0.000090 0.171327 0.803085 11.00000 0.08244 0.07284 = 0.14489 0.05417 0.05927 0.02471 O5 4 0.165713 0.046199 0.796945 11.00000 0.08811 0.06143 = 0.09288 0.04557 0.01792 0.02045 O6 4 0.493991 0.549854 0.832453 11.00000 0.06187 0.06232 = 0.05307 0.01298 0.00698 0.01672 O7 4 0.634255 0.471266 0.744929 11.00000 0.05993 0.08783 = 0.06628 0.02616 0.01688 0.02046 O8 4 0.630198 0.108968 1.050366 11.00000 0.13987 0.14117 = 0.07981 0.05464 0.03789 0.06768 O9 4 0.740890 0.009939 0.962132 11.00000 0.10788 0.08772 = 0.09769 0.03059 0.01670 0.04427 CL1 5 -0.101507 0.718992 0.947503 11.00000 0.11419 0.07591 = 0.10675 0.00414 0.05633 0.03320 H1 2 0.320847 0.243823 0.493607 11.00000 0.07148 HKLF 4 REM jr637_a.res in P-1 REM R1 = 0.0498 for 4161 Fo > 4sig(Fo) and 0.0758 for all 5738 data REM 420 parameters refined using 0 restraints END WGHT 0.0729 0.4679 REM Highest difference peak 0.349, deepest hole -0.232, 1-sigma level 0.068 Q1 1 0.1463 0.0401 0.3852 11.00000 0.05 0.35 Q2 1 0.2155 0.3065 0.3769 11.00000 0.05 0.34 Q3 1 0.1591 0.4056 0.5454 11.00000 0.05 0.26 Q4 1 0.7256 0.1345 0.5867 11.00000 0.05 0.25 Q5 1 0.0941 0.1947 0.8398 11.00000 0.05 0.23 Q6 1 0.1885 0.1142 0.8233 11.00000 0.05 0.22 Q7 1 0.1197 0.5081 0.7871 11.00000 0.05 0.22 Q8 1 0.1688 0.1015 0.8449 11.00000 0.05 0.21 Q9 1 0.0169 0.6321 0.8525 11.00000 0.05 0.20 Q10 1 0.1371 0.1220 0.7933 11.00000 0.05 0.20 Q11 1 0.6155 0.1644 0.6281 11.00000 0.05 0.20 Q12 1 0.0922 0.0337 0.3158 11.00000 0.05 0.19 Q13 1 0.5569 0.3207 0.5552 11.00000 0.05 0.19 Q14 1 0.1690 0.1961 0.7644 11.00000 0.05 0.19 Q15 1 0.1793 0.4903 0.8325 11.00000 0.05 0.18 Q16 1 0.1616 -0.0014 0.8893 11.00000 0.05 0.18 Q17 1 0.1166 0.0598 0.7820 11.00000 0.05 0.18 Q18 1 0.2042 0.0179 0.8749 11.00000 0.05 0.18 Q19 1 0.7355 0.3571 0.6422 11.00000 0.05 0.18 Q20 1 0.0237 0.5742 0.9053 11.00000 0.05 0.18 ; _shelx_res_checksum 49097 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2386(5) 0.1573(7) 0.3578(2) 0.174(3) Uani 1 1 d . . . . . H1A H 0.1813 0.1288 0.3072 0.260 Uiso 1 1 calc R U . . . H1B H 0.3239 0.2272 0.3578 0.260 Uiso 1 1 calc R U . . . H1C H 0.2687 0.0806 0.3708 0.260 Uiso 1 1 calc R U . . . C2 C 0.0129(5) 0.1091(5) 0.4189(2) 0.155(2) Uani 1 1 d . . . . . H2A H -0.0473 0.0819 0.3691 0.233 Uiso 1 1 calc R U . . . H2B H 0.0401 0.0309 0.4315 0.233 Uiso 1 1 calc R U . . . H2C H -0.0411 0.1480 0.4576 0.233 Uiso 1 1 calc R U . . . C3 C 0.0999(6) 0.3339(5) 0.3973(2) 0.1486(19) Uani 1 1 d . . . . . H3A H 0.0396 0.3059 0.3476 0.223 Uiso 1 1 calc R U . . . H3B H 0.0446 0.3700 0.4362 0.223 Uiso 1 1 calc R U . . . H3C H 0.1849 0.4030 0.3960 0.223 Uiso 1 1 calc R U . . . C4 C 0.1478(3) 0.2126(3) 0.41644(14) 0.0740(8) Uani 1 1 d . . . . . C5 C 0.2085(3) 0.3156(2) 0.56017(13) 0.0518(5) Uani 1 1 d . . . . . C6 C 0.3358(2) 0.3525(2) 0.62806(12) 0.0460(5) Uani 1 1 d . . . . . H6 H 0.4211 0.4103 0.6142 0.055 Uiso 1 1 calc R U . . . C7 C 0.3812(2) 0.2293(2) 0.64680(13) 0.0482(5) Uani 1 1 d . . . . . C8 C 0.3136(2) 0.1720(2) 0.69822(13) 0.0509(5) Uani 1 1 d . . . . . H8 H 0.3351 0.0922 0.7073 0.061 Uiso 1 1 calc R U . . . C9 C 0.2087(2) 0.2295(2) 0.74006(13) 0.0484(5) Uani 1 1 d . . . . . C10 C 0.2103(2) 0.3644(2) 0.74349(12) 0.0434(5) Uani 1 1 d . . . . . C11 C 0.1124(3) 0.1505(2) 0.78317(14) 0.0575(6) Uani 1 1 d . . . . . C12 C 0.0830(4) -0.0365(3) 0.84164(19) 0.0952(10) Uani 1 1 d . . . . . H12A H 0.1304 -0.1081 0.8482 0.143 Uiso 1 1 calc R U . . . H12B H 0.0788 0.0196 0.8916 0.143 Uiso 1 1 calc R U . . . H12C H -0.0149 -0.0758 0.8148 0.143 Uiso 1 1 calc R U . . . C13 C 0.5025(3) 0.1782(3) 0.61392(15) 0.0622(6) Uani 1 1 d . . . . . C14 C 0.6935(4) 0.2173(4) 0.5375(2) 0.1177(13) Uani 1 1 d . . . . . H14A H 0.7281 0.2749 0.5042 0.177 Uiso 1 1 calc R U . . . H14B H 0.7687 0.2307 0.5805 0.177 Uiso 1 1 calc R U . . . H14C H 0.6702 0.1234 0.5089 0.177 Uiso 1 1 calc R U . . . C15 C 0.1323(2) 0.4489(2) 0.79577(12) 0.0438(5) Uani 1 1 d . . . . . C16 C 0.1556(2) 0.4693(2) 0.87542(13) 0.0544(6) Uani 1 1 d . . . . . H16 H 0.2199 0.4263 0.8977 0.065 Uiso 1 1 calc R U . . . C17 C 0.0852(3) 0.5523(3) 0.92234(14) 0.0603(6) Uani 1 1 d . . . . . H17 H 0.1022 0.5660 0.9760 0.072 Uiso 1 1 calc R U . . . C18 C -0.0106(3) 0.6148(2) 0.88898(15) 0.0585(6) Uani 1 1 d . . . . . C19 C -0.0373(3) 0.5951(2) 0.80976(14) 0.0551(6) Uani 1 1 d . . . . . H19 H -0.1036 0.6366 0.7878 0.066 Uiso 1 1 calc R U . . . C20 C 0.0351(2) 0.5134(2) 0.76338(13) 0.0491(5) Uani 1 1 d . . . . . H20 H 0.0189 0.5011 0.7098 0.059 Uiso 1 1 calc R U . . . C21 C 0.3520(2) 0.5751(2) 0.71956(12) 0.0458(5) Uani 1 1 d . . . . . C22 C 0.4545(2) 0.6326(2) 0.78452(13) 0.0517(5) Uani 1 1 d . . . . . C23 C 0.5166(3) 0.7712(3) 0.80556(16) 0.0705(7) Uani 1 1 d . . . . . H23 H 0.5853 0.8094 0.8499 0.085 Uiso 1 1 calc R U . . . C24 C 0.4746(4) 0.8520(3) 0.75928(19) 0.0796(8) Uani 1 1 d . . . . . H24 H 0.5148 0.9457 0.7729 0.096 Uiso 1 1 calc R U . . . C25 C 0.3752(3) 0.7961(3) 0.69397(17) 0.0727(8) Uani 1 1 d . . . . . H25 H 0.3491 0.8514 0.6629 0.087 Uiso 1 1 calc R U . . . C26 C 0.3128(3) 0.6576(2) 0.67363(14) 0.0590(6) Uani 1 1 d . . . . . H26 H 0.2445 0.6198 0.6291 0.071 Uiso 1 1 calc R U . . . C27 C 0.5825(2) 0.4671(2) 0.80386(14) 0.0556(6) Uani 1 1 d . . . . . C28 C 0.6049(2) 0.3723(2) 0.85345(13) 0.0537(6) Uani 1 1 d . . . . . C29 C 0.5323(3) 0.3639(3) 0.91678(15) 0.0688(7) Uani 1 1 d . . . . . H29 H 0.4681 0.4200 0.9299 0.083 Uiso 1 1 calc R U . . . C30 C 0.5539(3) 0.2732(3) 0.96098(15) 0.0730(7) Uani 1 1 d . . . . . H30 H 0.5053 0.2675 1.0038 0.088 Uiso 1 1 calc R U . . . C31 C 0.6490(3) 0.1919(3) 0.93987(14) 0.0586(6) Uani 1 1 d . . . . . C32 C 0.7233(3) 0.1988(3) 0.87825(15) 0.0642(7) Uani 1 1 d . . . . . H32 H 0.7879 0.1428 0.8657 0.077 Uiso 1 1 calc R U . . . C33 C 0.7013(3) 0.2905(3) 0.83429(15) 0.0626(6) Uani 1 1 d . . . . . H33 H 0.7514 0.2966 0.7921 0.075 Uiso 1 1 calc R U . . . N1 N 0.2401(3) 0.2546(3) 0.49252(12) 0.0719(7) Uani 1 1 d . . . . . N2 N 0.29305(18) 0.43044(16) 0.69775(10) 0.0442(4) Uani 1 1 d . . . . . N3 N 0.6757(3) 0.0964(2) 0.98770(14) 0.0728(6) Uani 1 1 d . . . . . O1 O 0.0912(2) 0.3427(2) 0.56978(11) 0.0896(7) Uani 1 1 d . . . . . O2 O 0.5444(2) 0.0819(2) 0.62678(14) 0.1009(8) Uani 1 1 d . . . . . O3 O 0.5624(2) 0.25179(19) 0.56630(11) 0.0747(5) Uani 1 1 d . . . . . O4 O -0.0001(2) 0.1713(2) 0.80309(14) 0.0919(7) Uani 1 1 d . . . . . O5 O 0.1657(2) 0.04620(18) 0.79695(11) 0.0758(5) Uani 1 1 d . . . . . O6 O 0.49399(17) 0.54985(16) 0.83245(9) 0.0590(4) Uani 1 1 d . . . . . O7 O 0.63425(19) 0.47127(19) 0.74493(10) 0.0692(5) Uani 1 1 d . . . . . O8 O 0.6302(3) 0.1090(3) 1.05037(14) 0.1092(8) Uani 1 1 d . . . . . O9 O 0.7409(3) 0.0099(2) 0.96213(13) 0.0931(6) Uani 1 1 d . . . . . Cl1 Cl -0.10151(10) 0.71899(8) 0.94750(5) 0.0976(3) Uani 1 1 d . . . . . H1 H 0.321(3) 0.244(3) 0.4936(16) 0.071(9) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.147(4) 0.325(7) 0.055(2) -0.015(3) 0.004(2) 0.139(5) C2 0.154(4) 0.179(5) 0.082(3) 0.002(3) -0.013(3) -0.028(4) C3 0.207(5) 0.176(4) 0.088(3) 0.056(3) -0.010(3) 0.087(4) C4 0.0736(18) 0.110(2) 0.0453(14) 0.0143(14) 0.0045(12) 0.0442(17) C5 0.0557(14) 0.0549(13) 0.0507(13) 0.0160(10) 0.0091(11) 0.0217(11) C6 0.0490(12) 0.0429(11) 0.0488(12) 0.0129(9) 0.0119(10) 0.0130(9) C7 0.0470(12) 0.0424(11) 0.0549(13) 0.0093(10) 0.0035(10) 0.0139(9) C8 0.0544(13) 0.0381(11) 0.0623(14) 0.0139(10) 0.0031(11) 0.0155(10) C9 0.0502(12) 0.0397(11) 0.0580(13) 0.0163(10) 0.0070(10) 0.0116(9) C10 0.0441(11) 0.0420(11) 0.0454(11) 0.0144(9) 0.0039(9) 0.0099(9) C11 0.0648(15) 0.0410(12) 0.0668(15) 0.0175(11) 0.0103(12) 0.0076(11) C12 0.118(3) 0.0747(19) 0.101(2) 0.0579(18) 0.011(2) 0.0036(18) C13 0.0639(15) 0.0615(15) 0.0659(15) 0.0138(12) 0.0140(12) 0.0249(13) C14 0.101(3) 0.139(3) 0.146(3) 0.051(3) 0.075(2) 0.061(2) C15 0.0459(11) 0.0385(11) 0.0483(12) 0.0147(9) 0.0087(9) 0.0075(9) C16 0.0515(13) 0.0609(14) 0.0535(14) 0.0208(11) 0.0078(11) 0.0117(11) C17 0.0603(15) 0.0657(15) 0.0490(13) 0.0102(11) 0.0134(11) 0.0032(12) C18 0.0603(14) 0.0430(12) 0.0689(16) 0.0068(11) 0.0248(12) 0.0050(11) C19 0.0537(13) 0.0442(12) 0.0723(16) 0.0188(11) 0.0144(11) 0.0150(10) C20 0.0528(13) 0.0443(12) 0.0518(12) 0.0145(10) 0.0065(10) 0.0121(10) C21 0.0529(12) 0.0366(11) 0.0511(12) 0.0134(9) 0.0148(10) 0.0119(9) C22 0.0564(13) 0.0470(12) 0.0530(13) 0.0135(10) 0.0129(11) 0.0111(10) C23 0.0772(17) 0.0536(15) 0.0681(16) 0.0004(13) 0.0123(13) 0.0016(13) C24 0.102(2) 0.0371(13) 0.097(2) 0.0130(14) 0.0294(19) 0.0067(14) C25 0.097(2) 0.0446(14) 0.086(2) 0.0273(14) 0.0230(17) 0.0220(14) C26 0.0702(15) 0.0488(13) 0.0657(15) 0.0224(11) 0.0145(12) 0.0199(11) C27 0.0443(12) 0.0622(14) 0.0550(14) 0.0103(11) 0.0022(11) 0.0070(11) C28 0.0458(12) 0.0596(14) 0.0508(13) 0.0088(11) 0.0016(10) 0.0082(10) C29 0.0663(16) 0.0897(19) 0.0612(15) 0.0230(14) 0.0127(13) 0.0360(14) C30 0.0716(17) 0.101(2) 0.0597(15) 0.0288(15) 0.0189(13) 0.0350(16) C31 0.0537(13) 0.0635(15) 0.0561(14) 0.0143(11) -0.0004(11) 0.0115(11) C32 0.0585(15) 0.0630(15) 0.0715(16) 0.0129(13) 0.0120(13) 0.0180(12) C33 0.0589(14) 0.0676(16) 0.0642(15) 0.0171(13) 0.0173(12) 0.0161(12) N1 0.0643(14) 0.1117(19) 0.0474(12) 0.0104(11) 0.0058(10) 0.0478(14) N2 0.0508(10) 0.0358(9) 0.0478(10) 0.0121(8) 0.0095(8) 0.0109(8) N3 0.0720(14) 0.0778(16) 0.0711(15) 0.0218(12) 0.0042(12) 0.0215(12) O1 0.0691(12) 0.1367(18) 0.0641(11) 0.0011(11) 0.0022(9) 0.0544(12) O2 0.1059(16) 0.0959(15) 0.143(2) 0.0586(15) 0.0560(15) 0.0698(14) O3 0.0741(12) 0.0826(12) 0.0828(12) 0.0264(10) 0.0342(10) 0.0363(10) O4 0.0824(14) 0.0728(13) 0.145(2) 0.0542(13) 0.0593(14) 0.0247(11) O5 0.0881(13) 0.0614(11) 0.0929(13) 0.0456(10) 0.0179(10) 0.0204(9) O6 0.0619(10) 0.0623(10) 0.0531(9) 0.0130(8) 0.0070(8) 0.0167(8) O7 0.0599(10) 0.0878(13) 0.0663(11) 0.0262(9) 0.0169(9) 0.0205(9) O8 0.140(2) 0.141(2) 0.0798(15) 0.0546(14) 0.0379(14) 0.0677(17) O9 0.1079(16) 0.0877(15) 0.0977(15) 0.0306(12) 0.0167(13) 0.0443(13) Cl1 0.1142(7) 0.0759(5) 0.1067(6) 0.0041(4) 0.0563(5) 0.0332(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' 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 C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C2 109.6(3) . . ? N1 C4 C1 107.3(2) . . ? C2 C4 C1 112.1(4) . . ? N1 C4 C3 109.9(3) . . ? C2 C4 C3 107.6(4) . . ? C1 C4 C3 110.4(3) . . ? O1 C5 N1 124.1(2) . . ? O1 C5 C6 121.3(2) . . ? N1 C5 C6 114.51(19) . . ? N2 C6 C7 108.53(16) . . ? N2 C6 C5 109.57(16) . . ? C7 C6 C5 113.60(17) . . ? N2 C6 H6 108.3 . . ? C7 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C8 C7 C13 120.0(2) . . ? C8 C7 C6 118.15(19) . . ? C13 C7 C6 121.8(2) . . ? C7 C8 C9 122.13(19) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 117.39(19) . . ? C10 C9 C11 121.4(2) . . ? C8 C9 C11 121.02(19) . . ? N2 C10 C9 119.18(19) . . ? N2 C10 C15 115.60(16) . . ? C9 C10 C15 125.18(18) . . ? O4 C11 O5 122.4(2) . . ? O4 C11 C9 126.6(2) . . ? O5 C11 C9 111.0(2) . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O3 123.0(2) . . ? O2 C13 C7 125.1(2) . . ? O3 C13 C7 112.0(2) . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.8(2) . . ? C16 C15 C10 122.56(18) . . ? C20 C15 C10 118.65(18) . . ? C17 C16 C15 121.0(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C16 119.2(2) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C19 C18 C17 121.1(2) . . ? C19 C18 Cl1 119.2(2) . . ? C17 C18 Cl1 119.7(2) . . ? C18 C19 C20 119.3(2) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C19 C20 C15 120.7(2) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C22 C21 C26 119.1(2) . . ? C22 C21 N2 120.05(18) . . ? C26 C21 N2 120.7(2) . . ? C21 C22 C23 121.3(2) . . ? C21 C22 O6 119.69(19) . . ? C23 C22 O6 119.0(2) . . ? C22 C23 C24 118.6(3) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C25 C24 C23 120.7(2) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 120.3(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 119.9(2) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? O7 C27 O6 122.9(2) . . ? O7 C27 C28 124.9(2) . . ? O6 C27 C28 112.1(2) . . ? C33 C28 C29 119.8(2) . . ? C33 C28 C27 117.9(2) . . ? C29 C28 C27 122.3(2) . . ? C28 C29 C30 120.8(2) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C31 C30 C29 118.0(2) . . ? C31 C30 H30 121.0 . . ? C29 C30 H30 121.0 . . ? C32 C31 C30 122.6(2) . . ? C32 C31 N3 118.8(2) . . ? C30 C31 N3 118.6(2) . . ? C31 C32 C33 119.1(2) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? C28 C33 C32 119.7(2) . . ? C28 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C5 N1 C4 128.4(2) . . ? C5 N1 H1 115(2) . . ? C4 N1 H1 117(2) . . ? C10 N2 C21 121.77(17) . . ? C10 N2 C6 120.32(16) . . ? C21 N2 C6 117.66(16) . . ? O9 N3 O8 124.0(2) . . ? O9 N3 C31 118.1(2) . . ? O8 N3 C31 117.9(2) . . ? C13 O3 C14 115.6(2) . . ? C11 O5 C12 116.2(2) . . ? C27 O6 C22 115.62(17) . . ? 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 C1 C4 1.500(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.488(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.509(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 N1 1.469(3) . ? C5 O1 1.210(3) . ? C5 N1 1.323(3) . ? C5 C6 1.547(3) . ? C6 N2 1.463(3) . ? C6 C7 1.514(3) . ? C6 H6 0.9800 . ? C7 C8 1.333(3) . ? C7 C13 1.467(3) . ? C8 C9 1.436(3) . ? C8 H8 0.9300 . ? C9 C10 1.376(3) . ? C9 C11 1.471(3) . ? C10 N2 1.367(3) . ? C10 C15 1.483(3) . ? C11 O4 1.190(3) . ? C11 O5 1.337(3) . ? C12 O5 1.449(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O2 1.200(3) . ? C13 O3 1.343(3) . ? C14 O3 1.457(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.380(3) . ? C15 C20 1.391(3) . ? C16 C17 1.376(3) . ? C16 H16 0.9300 . ? C17 C18 1.375(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(3) . ? C18 Cl1 1.739(2) . ? C19 C20 1.375(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.373(3) . ? C21 C26 1.382(3) . ? C21 N2 1.432(3) . ? C22 C23 1.380(3) . ? C22 O6 1.411(3) . ? C23 C24 1.382(4) . ? C23 H23 0.9300 . ? C24 C25 1.361(4) . ? C24 H24 0.9300 . ? C25 C26 1.379(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 O7 1.202(3) . ? C27 O6 1.364(3) . ? C27 C28 1.487(3) . ? C28 C33 1.377(3) . ? C28 C29 1.380(3) . ? C29 C30 1.382(4) . ? C29 H29 0.9300 . ? C30 C31 1.369(4) . ? C30 H30 0.9300 . ? C31 C32 1.360(3) . ? C31 N3 1.481(3) . ? C32 C33 1.388(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? N1 H1 0.79(3) . ? N3 O9 1.215(3) . ? N3 O8 1.222(3) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2C O1 0.96 2.52 3.110(5) 119.8 . C3 H3B O1 0.96 2.47 3.067(4) 120.1 . C19 H19 O7 0.93 2.63 3.093(3) 111.6 1_455 C23 H23 O9 0.93 2.61 3.478(4) 154.6 1_565 C32 H32 O4 0.93 2.37 3.065(3) 131.7 1_655 N1 H1 O3 0.79(3) 2.49(3) 3.199(3) 151(3) . 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 O1 C5 C6 N2 -4.7(3) . . . . ? N1 C5 C6 N2 174.7(2) . . . . ? O1 C5 C6 C7 116.9(3) . . . . ? N1 C5 C6 C7 -63.7(3) . . . . ? N2 C6 C7 C8 32.7(3) . . . . ? C5 C6 C7 C8 -89.5(2) . . . . ? N2 C6 C7 C13 -143.3(2) . . . . ? C5 C6 C7 C13 94.6(2) . . . . ? C13 C7 C8 C9 171.2(2) . . . . ? C6 C7 C8 C9 -4.8(3) . . . . ? C7 C8 C9 C10 -18.7(3) . . . . ? C7 C8 C9 C11 166.5(2) . . . . ? C8 C9 C10 N2 10.3(3) . . . . ? C11 C9 C10 N2 -174.97(19) . . . . ? C8 C9 C10 C15 -167.40(19) . . . . ? C11 C9 C10 C15 7.4(3) . . . . ? C10 C9 C11 O4 25.6(4) . . . . ? C8 C9 C11 O4 -159.8(3) . . . . ? C10 C9 C11 O5 -155.7(2) . . . . ? C8 C9 C11 O5 18.9(3) . . . . ? C8 C7 C13 O2 3.6(4) . . . . ? C6 C7 C13 O2 179.5(2) . . . . ? C8 C7 C13 O3 -176.9(2) . . . . ? C6 C7 C13 O3 -1.0(3) . . . . ? N2 C10 C15 C16 -120.5(2) . . . . ? C9 C10 C15 C16 57.3(3) . . . . ? N2 C10 C15 C20 57.6(3) . . . . ? C9 C10 C15 C20 -124.7(2) . . . . ? C20 C15 C16 C17 -0.4(3) . . . . ? C10 C15 C16 C17 177.6(2) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C16 C17 C18 Cl1 179.49(17) . . . . ? C17 C18 C19 C20 -1.2(3) . . . . ? Cl1 C18 C19 C20 179.65(17) . . . . ? C18 C19 C20 C15 1.2(3) . . . . ? C16 C15 C20 C19 -0.5(3) . . . . ? C10 C15 C20 C19 -178.60(19) . . . . ? C26 C21 C22 C23 1.3(3) . . . . ? N2 C21 C22 C23 177.9(2) . . . . ? C26 C21 C22 O6 179.17(19) . . . . ? N2 C21 C22 O6 -4.2(3) . . . . ? C21 C22 C23 C24 -0.6(4) . . . . ? O6 C22 C23 C24 -178.5(2) . . . . ? C22 C23 C24 C25 -0.6(4) . . . . ? C23 C24 C25 C26 1.1(4) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? C22 C21 C26 C25 -0.8(3) . . . . ? N2 C21 C26 C25 -177.4(2) . . . . ? O7 C27 C28 C33 5.5(4) . . . . ? O6 C27 C28 C33 -175.1(2) . . . . ? O7 C27 C28 C29 -174.2(2) . . . . ? O6 C27 C28 C29 5.2(3) . . . . ? C33 C28 C29 C30 -0.7(4) . . . . ? C27 C28 C29 C30 179.0(2) . . . . ? C28 C29 C30 C31 -0.2(4) . . . . ? C29 C30 C31 C32 0.8(4) . . . . ? C29 C30 C31 N3 178.7(2) . . . . ? C30 C31 C32 C33 -0.7(4) . . . . ? N3 C31 C32 C33 -178.5(2) . . . . ? C29 C28 C33 C32 0.8(4) . . . . ? C27 C28 C33 C32 -178.8(2) . . . . ? C31 C32 C33 C28 -0.2(4) . . . . ? O1 C5 N1 C4 2.7(5) . . . . ? C6 C5 N1 C4 -176.7(3) . . . . ? C2 C4 N1 C5 -62.1(4) . . . . ? C1 C4 N1 C5 176.0(4) . . . . ? C3 C4 N1 C5 56.0(4) . . . . ? C9 C10 N2 C21 -152.4(2) . . . . ? C15 C10 N2 C21 25.5(3) . . . . ? C9 C10 N2 C6 21.7(3) . . . . ? C15 C10 N2 C6 -160.41(17) . . . . ? C22 C21 N2 C10 64.4(3) . . . . ? C26 C21 N2 C10 -119.0(2) . . . . ? C22 C21 N2 C6 -109.9(2) . . . . ? C26 C21 N2 C6 66.7(3) . . . . ? C7 C6 N2 C10 -41.9(2) . . . . ? C5 C6 N2 C10 82.7(2) . . . . ? C7 C6 N2 C21 132.47(18) . . . . ? C5 C6 N2 C21 -103.0(2) . . . . ? C32 C31 N3 O9 -13.6(4) . . . . ? C30 C31 N3 O9 168.5(3) . . . . ? C32 C31 N3 O8 166.7(3) . . . . ? C30 C31 N3 O8 -11.2(4) . . . . ? O2 C13 O3 C14 -6.7(4) . . . . ? C7 C13 O3 C14 173.8(3) . . . . ? O4 C11 O5 C12 -3.4(4) . . . . ? C9 C11 O5 C12 177.8(2) . . . . ? O7 C27 O6 C22 5.9(3) . . . . ? C28 C27 O6 C22 -173.46(18) . . . . ? C21 C22 O6 C27 74.6(3) . . . . ? C23 C22 O6 C27 -107.5(2) . . . . ?