#------------------------------------------------------------------------------ #$Date: 2020-04-25 01:00:20 +0300 (Sat, 25 Apr 2020) $ #$Revision: 251158 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126448.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_7126448 loop_ _publ_author_name 'Wang, Donglei' 'Jiang, Qianwen' 'Yang, Xiaoyu' _publ_section_title ; Atroposelective Synthesis of Configurationally Stable Nonbiaryl N-C Atropisomers through Direct Asymmetric Aminations of 1,3-Benzenediamines ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D0CC02368J _journal_year 2020 _chemical_formula_moiety 'C31 H38 N4 O5' _chemical_formula_sum 'C31 H38 N4 O5' _chemical_formula_weight 546.65 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-03-06 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2020-03-07 deposited with the CCDC. 2020-04-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.1246(3) _cell_length_b 16.0039(5) _cell_length_c 18.3736(6) _cell_measurement_reflns_used 9548 _cell_measurement_temperature 149.99 _cell_measurement_theta_max 78.80 _cell_measurement_theta_min 5.17 _cell_volume 2977.13(16) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 149.99 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 61146 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.180 _diffrn_reflns_theta_min 3.663 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_T_max 0.7542 _exptl_absorpt_correction_T_min 0.6297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1259 before and 0.0786 after correction. The Ratio of minimum to maximum transmission is 0.8349. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.220 _exptl_crystal_description plate _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.344 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details ; Flack x determined using 2437 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(7) _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 6406 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0411 _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^)+(0.0496P)^2^+0.9135P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1029 _refine_ls_wR_factor_ref 0.1066 _reflns_Friedel_coverage 0.775 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.986 _reflns_number_gt 5918 _reflns_number_total 6406 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02368j2.cif _cod_data_source_block cu_wdl6_55_0m _cod_database_code 7126448 _shelx_shelxl_version_number 2018/3 _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_max 0.987 _shelx_estimated_absorpt_t_min 0.936 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Rotating group: N00B(H00A,H00B) 3.b Secondary CH2 refined with riding coordinates: C00Z(H00X,H00Z), C4(H4A,H4B) 3.c Aromatic/amide H refined with riding coordinates: N007(H007), N008(H008), C00I(H00I), C00J(H00J), C00O(H00O), C00Y(H00Y), C010(H010), C012(H012), C014(H014), C2(H2), C3(H3), C7(H7), C6(H6), C5(H5) 3.d Idealised Me refined as rotating group: C00N(H00C,H00D,H00E), C00P(H00F,H00G,H00H), C00Q(H00K,H00L,H00M), C00R(H00N, H00P,H00Q), C00S(H00R,H00S,H00T), C00X(H00U,H00V,H00W) ; _shelx_res_file ; TITL cu_wdl6_55_0m_a.res in P2(1)2(1)2(1) cu_wdl6_55_0m.res created by SHELXL-2018/3 at 19:26:43 on 06-Mar-2020 REM Old TITL cu_wdl6_55_0m in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.141, Rweak 0.028, Alpha 0.001, Orientation as input REM Flack x = 0.072 ( 0.062 ) from Parsons' quotients REM Formula found by SHELXT: C32 N3 O5 CELL 1.54178 10.1246 16.0039 18.3736 90 90 90 ZERR 4 0.0003 0.0005 0.0006 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 124 152 16 20 ISOR 0.005 0.01 C5 C6 C7 L.S. 10 PLAN 5 SIZE 0.1 0.1 0.02 TEMP -123.16 CONF LIST 6 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.049600 0.913500 EXTI 0.001374 FVAR 0.57296 O001 4 0.569976 0.248436 0.832688 11.00000 0.04849 0.02326 = 0.03162 -0.00281 -0.00615 0.00618 O002 4 0.730575 0.482953 0.731775 11.00000 0.02907 0.03767 = 0.05189 -0.01562 -0.00383 -0.00069 O003 4 0.667018 0.606549 0.779889 11.00000 0.04985 0.02945 = 0.04448 -0.01082 -0.00423 -0.00780 O004 4 0.294126 0.652015 0.811649 11.00000 0.05274 0.02552 = 0.03641 0.00458 0.01597 0.00978 O005 4 0.388033 0.532652 0.851273 11.00000 0.06816 0.02730 = 0.03589 0.00695 0.01528 0.01175 N006 3 0.519984 0.521616 0.722552 11.00000 0.03151 0.02013 = 0.02804 -0.00332 0.00164 0.00110 N007 3 0.497282 0.379173 0.804878 11.00000 0.03883 0.01949 = 0.02476 -0.00280 -0.00125 0.00179 AFIX 43 H007 2 0.476781 0.427668 0.824423 11.00000 -1.20000 AFIX 0 N008 3 0.419881 0.580273 0.734880 11.00000 0.03600 0.02225 = 0.03058 0.00257 0.00446 0.00494 AFIX 43 H008 2 0.390334 0.612915 0.699945 11.00000 -1.20000 AFIX 0 C009 1 0.642540 0.542369 0.747782 11.00000 0.03700 0.02579 = 0.02996 -0.00308 0.00086 -0.00248 C00A 1 0.476409 0.438882 0.609444 11.00000 0.02565 0.02571 = 0.02803 0.00089 0.00002 -0.00042 N00B 3 0.408499 0.212721 0.591420 11.00000 0.07038 0.02427 = 0.03089 -0.00280 -0.00954 -0.00439 AFIX 7 H00A 2 0.361194 0.181362 0.621209 11.00000 -1.20000 H00B 2 0.364385 0.219701 0.550379 11.00000 -1.20000 AFIX 0 C00C 1 0.370248 0.584203 0.804288 11.00000 0.04036 0.02003 = 0.03644 0.00113 0.00707 0.00140 C00D 1 0.476845 0.371666 0.728995 11.00000 0.02692 0.02409 = 0.02524 -0.00143 -0.00124 0.00123 C00E 1 0.431414 0.289345 0.623091 11.00000 0.03316 0.02469 = 0.02822 -0.00323 -0.00292 0.00173 C00F 1 0.489843 0.444284 0.685661 11.00000 0.02811 0.02100 = 0.02811 -0.00227 0.00006 -0.00065 C00G 1 0.544796 0.320270 0.850915 11.00000 0.02924 0.02185 = 0.02719 -0.00207 -0.00002 -0.00049 C00I 1 0.446487 0.295598 0.698352 11.00000 0.03584 0.02051 = 0.02746 0.00072 -0.00245 0.00095 AFIX 43 H00I 2 0.435863 0.247649 0.728265 11.00000 -1.20000 AFIX 0 C00J 1 0.446337 0.360740 0.580675 11.00000 0.03289 0.02853 = 0.02548 -0.00080 -0.00289 0.00005 AFIX 43 H00J 2 0.435448 0.355893 0.529494 11.00000 -1.20000 AFIX 0 C00K 1 0.564296 0.349994 0.929990 11.00000 0.03831 0.02822 = 0.02514 -0.00249 -0.00387 0.00166 C00L 1 0.487455 0.513179 0.556213 11.00000 0.03848 0.02858 = 0.02922 0.00549 -0.00099 -0.00752 C00N 1 0.585590 0.581391 0.578967 11.00000 0.04019 0.02960 = 0.03248 0.00177 0.00345 -0.00796 AFIX 137 H00C 2 0.548787 0.613365 0.619685 11.00000 -1.50000 H00D 2 0.601728 0.618903 0.537758 11.00000 -1.50000 H00E 2 0.668942 0.555476 0.593993 11.00000 -1.50000 AFIX 0 C00O 1 0.867415 0.344804 0.783489 11.00000 0.03869 0.07761 = 0.03957 -0.00576 0.00017 0.01566 AFIX 43 H00O 2 0.776356 0.341203 0.771414 11.00000 -1.20000 AFIX 0 C00P 1 0.638722 0.433690 0.932262 11.00000 0.05596 0.03728 = 0.03623 -0.00632 -0.01166 -0.00477 AFIX 137 H00F 2 0.720061 0.429195 0.903616 11.00000 -1.50000 H00G 2 0.660828 0.447443 0.982789 11.00000 -1.50000 H00H 2 0.582716 0.477782 0.911829 11.00000 -1.50000 AFIX 0 C00Q 1 0.645462 0.284900 0.970665 11.00000 0.06923 0.03678 = 0.03345 -0.00099 -0.01929 0.00999 AFIX 137 H00K 2 0.598056 0.231512 0.970796 11.00000 -1.50000 H00L 2 0.659556 0.303465 1.020895 11.00000 -1.50000 H00M 2 0.731007 0.277833 0.946479 11.00000 -1.50000 AFIX 0 C00R 1 0.348932 0.550653 0.547442 11.00000 0.04311 0.04004 = 0.06570 0.02284 -0.01265 -0.00409 AFIX 137 H00N 2 0.287365 0.506947 0.531799 11.00000 -1.50000 H00P 2 0.351361 0.595154 0.510828 11.00000 -1.50000 H00Q 2 0.319564 0.573800 0.594095 11.00000 -1.50000 AFIX 0 C00S 1 0.534825 0.482888 0.480758 11.00000 0.07682 0.04488 = 0.02593 0.00240 0.00246 -0.02633 AFIX 137 H00R 2 0.618405 0.452617 0.486097 11.00000 -1.50000 H00S 2 0.547875 0.531155 0.448732 11.00000 -1.50000 H00T 2 0.468242 0.445680 0.459585 11.00000 -1.50000 AFIX 0 C00T 1 0.932020 0.420607 0.777506 11.00000 0.03208 0.08658 = 0.03613 -0.01871 -0.00244 0.00657 C00X 1 0.428376 0.359846 0.965097 11.00000 0.04588 0.06619 = 0.03186 -0.00059 0.00549 0.00014 AFIX 137 H00U 2 0.379620 0.404496 0.940388 11.00000 -1.50000 H00V 2 0.438977 0.374083 1.016643 11.00000 -1.50000 H00W 2 0.379355 0.307278 0.960777 11.00000 -1.50000 AFIX 0 C00Y 1 1.066150 0.424636 0.794343 11.00000 0.03533 0.13348 = 0.05072 -0.02849 -0.00749 0.00384 AFIX 43 H00Y 2 1.111955 0.476208 0.790047 11.00000 -1.20000 AFIX 0 C00Z 1 0.864676 0.499051 0.754862 11.00000 0.03171 0.06023 = 0.08403 -0.02200 -0.00665 -0.00557 AFIX 23 H00X 2 0.863908 0.538825 0.796127 11.00000 -1.20000 H00Z 2 0.914389 0.525064 0.714372 11.00000 -1.20000 AFIX 0 C010 1 0.934071 0.273765 0.806961 11.00000 0.06528 0.10219 = 0.04700 0.00961 0.00341 0.03463 AFIX 43 H010 2 0.888687 0.222073 0.811512 11.00000 -1.20000 AFIX 0 C012 1 1.132705 0.354166 0.817200 11.00000 0.04455 0.18176 = 0.05640 -0.01454 -0.01782 0.03444 AFIX 43 H012 2 1.224101 0.357473 0.828541 11.00000 -1.20000 AFIX 0 C014 1 1.067449 0.279062 0.823674 11.00000 0.06698 0.15599 = 0.05856 0.01407 -0.00683 0.05164 AFIX 43 H014 2 1.113805 0.230801 0.839605 11.00000 -1.20000 AFIX 0 C1 1 0.151917 0.735271 0.888332 11.00000 0.04511 0.03190 = 0.03043 0.00497 0.01198 0.00703 C2 1 0.199275 0.813193 0.906842 11.00000 0.04742 0.04510 = 0.03784 0.00291 0.00076 -0.00394 AFIX 43 H2 2 0.291157 0.820957 0.914850 11.00000 -1.20000 AFIX 0 C3 1 0.020094 0.725996 0.875214 11.00000 0.05231 0.06238 = 0.05260 0.00872 0.00282 -0.01908 AFIX 43 H3 2 -0.013547 0.672914 0.861356 11.00000 -1.20000 AFIX 0 C4 1 0.247880 0.663787 0.886741 11.00000 0.08072 0.04467 = 0.03934 0.01012 0.02319 0.02504 AFIX 23 H4A 2 0.323754 0.675939 0.919039 11.00000 -1.20000 H4B 2 0.204313 0.612199 0.904284 11.00000 -1.20000 AFIX 0 C7 1 0.113827 0.880100 0.913818 11.00000 0.11144 0.03456 = 0.04611 -0.00288 0.01366 0.00803 AFIX 43 H7 2 0.146720 0.933481 0.927341 11.00000 -1.20000 AFIX 0 C6 1 -0.017250 0.869302 0.901287 11.00000 0.08804 0.07488 = 0.06676 0.02629 0.03577 0.05015 AFIX 43 H6 2 -0.075978 0.915267 0.906096 11.00000 -1.20000 AFIX 0 C5 1 -0.064882 0.793048 0.881893 11.00000 0.03538 0.12564 = 0.07632 0.04170 0.01285 0.01052 AFIX 43 H5 2 -0.156603 0.785903 0.872941 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_wdl6_55_0m_a.res in P2(1)2(1)2(1) REM wR2 = 0.1066, GooF = S = 1.036, Restrained GooF = 1.080 for all data REM R1 = 0.0411 for 5918 Fo > 4sig(Fo) and 0.0456 for all 6406 data REM 369 parameters refined using 18 restraints END WGHT 0.0520 0.8860 REM Highest difference peak 0.344, deepest hole -0.248, 1-sigma level 0.037 Q1 1 0.1689 0.6419 0.8603 11.00000 0.05 0.34 Q2 1 0.4368 0.6351 0.7160 11.00000 0.05 0.30 Q3 1 0.4114 0.1605 0.6148 11.00000 0.05 0.21 Q4 1 1.0749 0.3250 0.8445 11.00000 0.05 0.20 Q5 1 0.4091 0.1948 0.5408 11.00000 0.05 0.19 ; _shelx_res_checksum 57952 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' '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 _atom_site_disorder_assembly _atom_site_disorder_group O001 O 0.56998(19) 0.24844(10) 0.83269(9) 0.0345(4) Uani 1 1 d . . . . . O002 O 0.73058(16) 0.48295(11) 0.73177(11) 0.0395(4) Uani 1 1 d . . . . . O003 O 0.66702(19) 0.60655(11) 0.77989(11) 0.0413(4) Uani 1 1 d . . . . . O004 O 0.29413(19) 0.65202(10) 0.81165(10) 0.0382(4) Uani 1 1 d . . . . . O005 O 0.3880(2) 0.53265(11) 0.85127(10) 0.0438(5) Uani 1 1 d . . . . . N006 N 0.51998(18) 0.52162(11) 0.72255(10) 0.0266(4) Uani 1 1 d . . . . . N007 N 0.4973(2) 0.37917(11) 0.80488(10) 0.0277(4) Uani 1 1 d . . . . . H007 H 0.476781 0.427668 0.824423 0.033 Uiso 1 1 calc R U . . . N008 N 0.4199(2) 0.58027(11) 0.73488(11) 0.0296(4) Uani 1 1 d . . . . . H008 H 0.390334 0.612915 0.699945 0.036 Uiso 1 1 calc R U . . . C009 C 0.6425(2) 0.54237(14) 0.74778(13) 0.0309(5) Uani 1 1 d . . . . . C00A C 0.4764(2) 0.43888(14) 0.60944(12) 0.0265(4) Uani 1 1 d . . . . . N00B N 0.4085(3) 0.21272(13) 0.59142(12) 0.0418(5) Uani 1 1 d . . . . . H00A H 0.361194 0.181362 0.621209 0.050 Uiso 1 1 d R U . . . H00B H 0.364385 0.219701 0.550379 0.050 Uiso 1 1 d R U . . . C00C C 0.3702(3) 0.58420(14) 0.80429(13) 0.0323(5) Uani 1 1 d . . . . . C00D C 0.4768(2) 0.37167(13) 0.72900(12) 0.0254(4) Uani 1 1 d . . . . . C00E C 0.4314(2) 0.28935(14) 0.62309(12) 0.0287(4) Uani 1 1 d . . . . . C00F C 0.4898(2) 0.44428(13) 0.68566(12) 0.0257(4) Uani 1 1 d . . . . . C00G C 0.5448(2) 0.32027(13) 0.85092(12) 0.0261(4) Uani 1 1 d . . . . . C00I C 0.4465(2) 0.29560(13) 0.69835(12) 0.0279(4) Uani 1 1 d . . . . . H00I H 0.435863 0.247649 0.728265 0.034 Uiso 1 1 calc R U . . . C00J C 0.4463(2) 0.36074(14) 0.58068(12) 0.0290(5) Uani 1 1 d . . . . . H00J H 0.435448 0.355893 0.529494 0.035 Uiso 1 1 calc R U . . . C00K C 0.5643(2) 0.34999(14) 0.92999(12) 0.0306(5) Uani 1 1 d . . . . . C00L C 0.4875(2) 0.51318(15) 0.55621(12) 0.0321(5) Uani 1 1 d . . . . . C00N C 0.5856(3) 0.58139(15) 0.57897(13) 0.0341(5) Uani 1 1 d . . . . . H00C H 0.548787 0.613365 0.619685 0.051 Uiso 1 1 calc R U . . . H00D H 0.601728 0.618903 0.537758 0.051 Uiso 1 1 calc R U . . . H00E H 0.668942 0.555476 0.593993 0.051 Uiso 1 1 calc R U . . . C00O C 0.8674(3) 0.3448(2) 0.78349(16) 0.0520(7) Uani 1 1 d . . . . . H00O H 0.776356 0.341203 0.771414 0.062 Uiso 1 1 calc R U . . . C00P C 0.6387(3) 0.43369(17) 0.93226(15) 0.0432(6) Uani 1 1 d . . . . . H00F H 0.720061 0.429195 0.903616 0.065 Uiso 1 1 calc R U . . . H00G H 0.660828 0.447443 0.982789 0.065 Uiso 1 1 calc R U . . . H00H H 0.582716 0.477782 0.911829 0.065 Uiso 1 1 calc R U . . . C00Q C 0.6455(3) 0.28490(18) 0.97067(15) 0.0465(7) Uani 1 1 d . . . . . H00K H 0.598056 0.231512 0.970796 0.070 Uiso 1 1 calc R U . . . H00L H 0.659556 0.303465 1.020895 0.070 Uiso 1 1 calc R U . . . H00M H 0.731007 0.277833 0.946479 0.070 Uiso 1 1 calc R U . . . C00R C 0.3489(3) 0.55065(18) 0.54744(19) 0.0496(7) Uani 1 1 d . . . . . H00N H 0.287365 0.506947 0.531799 0.074 Uiso 1 1 calc R U . . . H00P H 0.351361 0.595154 0.510828 0.074 Uiso 1 1 calc R U . . . H00Q H 0.319564 0.573800 0.594095 0.074 Uiso 1 1 calc R U . . . C00S C 0.5348(3) 0.48289(19) 0.48076(14) 0.0492(7) Uani 1 1 d . . . . . H00R H 0.618405 0.452617 0.486097 0.074 Uiso 1 1 calc R U . . . H00S H 0.547875 0.531155 0.448732 0.074 Uiso 1 1 calc R U . . . H00T H 0.468242 0.445680 0.459585 0.074 Uiso 1 1 calc R U . . . C00T C 0.9320(3) 0.4206(2) 0.77751(15) 0.0516(8) Uani 1 1 d . . . . . C00X C 0.4284(3) 0.3598(2) 0.96510(15) 0.0480(7) Uani 1 1 d . . . . . H00U H 0.379620 0.404496 0.940388 0.072 Uiso 1 1 calc R U . . . H00V H 0.438977 0.374083 1.016643 0.072 Uiso 1 1 calc R U . . . H00W H 0.379355 0.307278 0.960777 0.072 Uiso 1 1 calc R U . . . C00Y C 1.0662(3) 0.4246(3) 0.79434(19) 0.0732(12) Uani 1 1 d . . . . . H00Y H 1.111955 0.476208 0.790047 0.088 Uiso 1 1 calc R U . . . C00Z C 0.8647(3) 0.4991(2) 0.7549(2) 0.0587(9) Uani 1 1 d . . . . . H00X H 0.863908 0.538825 0.796127 0.070 Uiso 1 1 calc R U . . . H00Z H 0.914389 0.525064 0.714372 0.070 Uiso 1 1 calc R U . . . C010 C 0.9341(4) 0.2738(3) 0.80696(19) 0.0715(11) Uani 1 1 d . . . . . H010 H 0.888687 0.222073 0.811512 0.086 Uiso 1 1 calc R U . . . C012 C 1.1327(4) 0.3542(5) 0.8172(2) 0.0942(18) Uani 1 1 d . . . . . H012 H 1.224101 0.357473 0.828541 0.113 Uiso 1 1 calc R U . . . C014 C 1.0674(5) 0.2791(4) 0.8237(2) 0.0938(17) Uani 1 1 d . . . . . H014 H 1.113805 0.230801 0.839605 0.113 Uiso 1 1 calc R U . . . C1 C 0.1519(3) 0.73527(15) 0.88833(13) 0.0358(5) Uani 1 1 d . . . . . C2 C 0.1993(3) 0.81319(18) 0.90684(16) 0.0435(6) Uani 1 1 d . . . . . H2 H 0.291157 0.820957 0.914850 0.052 Uiso 1 1 calc R U . . . C3 C 0.0201(3) 0.7260(2) 0.87521(18) 0.0558(8) Uani 1 1 d . . . . . H3 H -0.013547 0.672914 0.861356 0.067 Uiso 1 1 calc R U . . . C4 C 0.2479(4) 0.6638(2) 0.88674(17) 0.0549(8) Uani 1 1 d . . . . . H4A H 0.323754 0.675939 0.919039 0.066 Uiso 1 1 calc R U . . . H4B H 0.204313 0.612199 0.904284 0.066 Uiso 1 1 calc R U . . . C7 C 0.1138(5) 0.8801(2) 0.91382(18) 0.0640(10) Uani 1 1 d . U . . . H7 H 0.146720 0.933481 0.927341 0.077 Uiso 1 1 calc R U . . . C6 C -0.0172(5) 0.8693(3) 0.9013(2) 0.0766(13) Uani 1 1 d . U . . . H6 H -0.075978 0.915267 0.906096 0.092 Uiso 1 1 calc R U . . . C5 C -0.0649(3) 0.7930(3) 0.8819(2) 0.0791(12) Uani 1 1 d . U . . . H5 H -0.156603 0.785903 0.872941 0.095 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 O001 0.0485(10) 0.0233(7) 0.0316(8) -0.0028(6) -0.0062(7) 0.0062(7) O002 0.0291(8) 0.0377(9) 0.0519(11) -0.0156(8) -0.0038(7) -0.0007(7) O003 0.0498(10) 0.0294(8) 0.0445(10) -0.0108(8) -0.0042(8) -0.0078(8) O004 0.0527(10) 0.0255(8) 0.0364(9) 0.0046(7) 0.0160(8) 0.0098(7) O005 0.0682(13) 0.0273(8) 0.0359(9) 0.0069(7) 0.0153(9) 0.0117(8) N006 0.0315(9) 0.0201(8) 0.0280(9) -0.0033(7) 0.0016(7) 0.0011(7) N007 0.0388(10) 0.0195(8) 0.0248(9) -0.0028(7) -0.0013(8) 0.0018(8) N008 0.0360(10) 0.0223(8) 0.0306(9) 0.0026(7) 0.0045(8) 0.0049(8) C009 0.0370(12) 0.0258(10) 0.0300(10) -0.0031(9) 0.0009(9) -0.0025(9) C00A 0.0256(10) 0.0257(10) 0.0280(10) 0.0009(8) 0.0000(8) -0.0004(8) N00B 0.0704(15) 0.0243(9) 0.0309(10) -0.0028(8) -0.0095(10) -0.0044(10) C00C 0.0404(12) 0.0200(10) 0.0364(12) 0.0011(9) 0.0071(10) 0.0014(9) C00D 0.0269(10) 0.0241(10) 0.0252(10) -0.0014(8) -0.0012(8) 0.0012(8) C00E 0.0332(11) 0.0247(10) 0.0282(10) -0.0032(9) -0.0029(9) 0.0017(9) C00F 0.0281(10) 0.0210(9) 0.0281(10) -0.0023(8) 0.0001(8) -0.0007(8) C00G 0.0292(11) 0.0218(10) 0.0272(10) -0.0021(8) 0.0000(8) -0.0005(8) C00I 0.0358(11) 0.0205(9) 0.0275(10) 0.0007(8) -0.0025(9) 0.0010(9) C00J 0.0329(11) 0.0285(11) 0.0255(10) -0.0008(8) -0.0029(8) 0.0000(9) C00K 0.0383(12) 0.0282(11) 0.0251(10) -0.0025(9) -0.0039(9) 0.0017(10) C00L 0.0385(12) 0.0286(11) 0.0292(11) 0.0055(9) -0.0010(9) -0.0075(10) C00N 0.0402(12) 0.0296(11) 0.0325(11) 0.0018(9) 0.0034(10) -0.0080(10) C00O 0.0387(14) 0.078(2) 0.0396(14) -0.0058(15) 0.0002(12) 0.0157(15) C00P 0.0560(16) 0.0373(13) 0.0362(12) -0.0063(11) -0.0117(12) -0.0048(12) C00Q 0.0692(18) 0.0368(13) 0.0334(12) -0.0010(11) -0.0193(13) 0.0100(13) C00R 0.0431(15) 0.0400(14) 0.0657(19) 0.0228(14) -0.0126(13) -0.0041(12) C00S 0.077(2) 0.0449(15) 0.0259(11) 0.0024(11) 0.0025(12) -0.0263(15) C00T 0.0321(12) 0.087(2) 0.0361(13) -0.0187(15) -0.0024(11) 0.0066(15) C00X 0.0459(15) 0.0662(19) 0.0319(12) -0.0006(12) 0.0055(11) 0.0001(14) C00Y 0.0353(15) 0.133(4) 0.0507(18) -0.028(2) -0.0075(14) 0.004(2) C00Z 0.0317(13) 0.0602(18) 0.084(2) -0.0220(17) -0.0066(14) -0.0056(13) C010 0.065(2) 0.102(3) 0.0470(17) 0.0096(19) 0.0034(16) 0.035(2) C012 0.045(2) 0.182(6) 0.056(2) -0.015(3) -0.0178(18) 0.034(3) C014 0.067(3) 0.156(5) 0.059(2) 0.014(3) -0.007(2) 0.052(3) C1 0.0451(14) 0.0319(12) 0.0304(11) 0.0050(9) 0.0120(10) 0.0070(10) C2 0.0474(15) 0.0451(15) 0.0378(13) 0.0029(12) 0.0008(12) -0.0039(12) C3 0.0523(17) 0.0624(19) 0.0526(17) 0.0087(15) 0.0028(14) -0.0191(15) C4 0.081(2) 0.0447(16) 0.0393(15) 0.0101(13) 0.0232(15) 0.0250(16) C7 0.111(3) 0.0346(14) 0.0461(16) -0.0029(13) 0.0137(18) 0.0080(17) C6 0.088(3) 0.075(2) 0.067(2) 0.0263(19) 0.036(2) 0.050(2) C5 0.0354(15) 0.126(3) 0.076(2) 0.042(2) 0.0129(16) 0.011(2) 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' 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 C009 O002 C00Z 115.8(2) . . ? C00C O004 C4 112.49(19) . . ? N008 N006 C00F 119.85(18) . . ? C009 N006 N008 116.09(17) . . ? C009 N006 C00F 124.05(18) . . ? C00D N007 H007 116.3 . . ? C00G N007 H007 116.3 . . ? C00G N007 C00D 127.46(18) . . ? N006 N008 H008 121.7 . . ? C00C N008 N006 116.50(18) . . ? C00C N008 H008 121.7 . . ? O002 C009 N006 111.00(18) . . ? O003 C009 O002 125.1(2) . . ? O003 C009 N006 123.9(2) . . ? C00F C00A C00L 125.1(2) . . ? C00J C00A C00F 117.0(2) . . ? C00J C00A C00L 117.87(19) . . ? H00A N00B H00B 109.1 . . ? C00E N00B H00A 109.6 . . ? C00E N00B H00B 109.5 . . ? O004 C00C N008 110.00(19) . . ? O005 C00C O004 124.6(2) . . ? O005 C00C N008 125.3(2) . . ? N007 C00D C00F 118.12(18) . . ? C00I C00D N007 120.7(2) . . ? C00I C00D C00F 121.1(2) . . ? N00B C00E C00I 120.1(2) . . ? N00B C00E C00J 120.9(2) . . ? C00J C00E C00I 119.0(2) . . ? C00A C00F N006 122.64(19) . . ? C00A C00F C00D 119.98(19) . . ? C00D C00F N006 117.36(18) . . ? O001 C00G N007 123.8(2) . . ? O001 C00G C00K 121.4(2) . . ? N007 C00G C00K 114.79(18) . . ? C00D C00I C00E 119.6(2) . . ? C00D C00I H00I 120.2 . . ? C00E C00I H00I 120.2 . . ? C00A C00J H00J 118.3 . . ? C00E C00J C00A 123.3(2) . . ? C00E C00J H00J 118.3 . . ? C00P C00K C00G 110.93(19) . . ? C00Q C00K C00G 108.70(19) . . ? C00Q C00K C00P 108.6(2) . . ? C00Q C00K C00X 110.5(2) . . ? C00X C00K C00G 108.3(2) . . ? C00X C00K C00P 109.9(2) . . ? C00A C00L C00S 110.4(2) . . ? C00N C00L C00A 114.98(19) . . ? C00N C00L C00S 105.5(2) . . ? C00R C00L C00A 107.55(19) . . ? C00R C00L C00N 110.0(2) . . ? C00R C00L C00S 108.2(2) . . ? C00L C00N H00C 109.5 . . ? C00L C00N H00D 109.5 . . ? C00L C00N H00E 109.5 . . ? H00C C00N H00D 109.5 . . ? H00C C00N H00E 109.5 . . ? H00D C00N H00E 109.5 . . ? C00T C00O H00O 119.6 . . ? C00T C00O C010 120.8(3) . . ? C010 C00O H00O 119.6 . . ? C00K C00P H00F 109.5 . . ? C00K C00P H00G 109.5 . . ? C00K C00P H00H 109.5 . . ? H00F C00P H00G 109.5 . . ? H00F C00P H00H 109.5 . . ? H00G C00P H00H 109.5 . . ? C00K C00Q H00K 109.5 . . ? C00K C00Q H00L 109.5 . . ? C00K C00Q H00M 109.5 . . ? H00K C00Q H00L 109.5 . . ? H00K C00Q H00M 109.5 . . ? H00L C00Q H00M 109.5 . . ? C00L C00R H00N 109.5 . . ? C00L C00R H00P 109.5 . . ? C00L C00R H00Q 109.5 . . ? H00N C00R H00P 109.5 . . ? H00N C00R H00Q 109.5 . . ? H00P C00R H00Q 109.5 . . ? C00L C00S H00R 109.5 . . ? C00L C00S H00S 109.5 . . ? C00L C00S H00T 109.5 . . ? H00R C00S H00S 109.5 . . ? H00R C00S H00T 109.5 . . ? H00S C00S H00T 109.5 . . ? C00O C00T C00Y 118.9(4) . . ? C00O C00T C00Z 123.1(2) . . ? C00Y C00T C00Z 118.0(4) . . ? C00K C00X H00U 109.5 . . ? C00K C00X H00V 109.5 . . ? C00K C00X H00W 109.5 . . ? H00U C00X H00V 109.5 . . ? H00U C00X H00W 109.5 . . ? H00V C00X H00W 109.5 . . ? C00T C00Y H00Y 119.8 . . ? C012 C00Y C00T 120.4(5) . . ? C012 C00Y H00Y 119.8 . . ? O002 C00Z C00T 111.2(3) . . ? O002 C00Z H00X 109.4 . . ? O002 C00Z H00Z 109.4 . . ? C00T C00Z H00X 109.4 . . ? C00T C00Z H00Z 109.4 . . ? H00X C00Z H00Z 108.0 . . ? C00O C010 H010 120.3 . . ? C014 C010 C00O 119.4(5) . . ? C014 C010 H010 120.3 . . ? C00Y C012 H012 119.8 . . ? C014 C012 C00Y 120.4(4) . . ? C014 C012 H012 119.8 . . ? C010 C014 H014 120.0 . . ? C012 C014 C010 120.1(5) . . ? C012 C014 H014 120.0 . . ? C2 C1 C4 118.0(3) . . ? C3 C1 C2 118.8(3) . . ? C3 C1 C4 123.1(3) . . ? C1 C2 H2 119.8 . . ? C1 C2 C7 120.4(3) . . ? C7 C2 H2 119.8 . . ? C1 C3 H3 119.7 . . ? C1 C3 C5 120.6(3) . . ? C5 C3 H3 119.7 . . ? O004 C4 C1 108.8(2) . . ? O004 C4 H4A 109.9 . . ? O004 C4 H4B 109.9 . . ? C1 C4 H4A 109.9 . . ? C1 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C2 C7 H7 120.1 . . ? C6 C7 C2 119.8(4) . . ? C6 C7 H7 120.1 . . ? C7 C6 H6 119.8 . . ? C7 C6 C5 120.3(3) . . ? C5 C6 H6 119.8 . . ? C3 C5 H5 120.0 . . ? C6 C5 C3 120.0(3) . . ? C6 C5 H5 120.0 . . ? 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 O001 C00G 1.224(3) . ? O002 C009 1.336(3) . ? O002 C00Z 1.446(3) . ? O003 C009 1.210(3) . ? O004 C00C 1.338(3) . ? O004 C4 1.469(3) . ? O005 C00C 1.208(3) . ? N006 N008 1.400(3) . ? N006 C009 1.366(3) . ? N006 C00F 1.444(3) . ? N007 H007 0.8800 . ? N007 C00D 1.415(3) . ? N007 C00G 1.355(3) . ? N008 H008 0.8800 . ? N008 C00C 1.372(3) . ? C00A C00F 1.410(3) . ? C00A C00J 1.391(3) . ? C00A C00L 1.544(3) . ? N00B H00A 0.8836 . ? N00B H00B 0.8835 . ? N00B C00E 1.377(3) . ? C00D C00F 1.415(3) . ? C00D C00I 1.376(3) . ? C00E C00I 1.395(3) . ? C00E C00J 1.391(3) . ? C00G C00K 1.541(3) . ? C00I H00I 0.9500 . ? C00J H00J 0.9500 . ? C00K C00P 1.537(3) . ? C00K C00Q 1.523(3) . ? C00K C00X 1.528(4) . ? C00L C00N 1.534(3) . ? C00L C00R 1.534(4) . ? C00L C00S 1.545(4) . ? C00N H00C 0.9800 . ? C00N H00D 0.9800 . ? C00N H00E 0.9800 . ? C00O H00O 0.9500 . ? C00O C00T 1.383(5) . ? C00O C010 1.391(5) . ? C00P H00F 0.9800 . ? C00P H00G 0.9800 . ? C00P H00H 0.9800 . ? C00Q H00K 0.9800 . ? C00Q H00L 0.9800 . ? C00Q H00M 0.9800 . ? C00R H00N 0.9800 . ? C00R H00P 0.9800 . ? C00R H00Q 0.9800 . ? C00S H00R 0.9800 . ? C00S H00S 0.9800 . ? C00S H00T 0.9800 . ? C00T C00Y 1.394(4) . ? C00T C00Z 1.488(5) . ? C00X H00U 0.9800 . ? C00X H00V 0.9800 . ? C00X H00W 0.9800 . ? C00Y H00Y 0.9500 . ? C00Y C012 1.379(7) . ? C00Z H00X 0.9900 . ? C00Z H00Z 0.9900 . ? C010 H010 0.9500 . ? C010 C014 1.387(7) . ? C012 H012 0.9500 . ? C012 C014 1.377(8) . ? C014 H014 0.9500 . ? C1 C2 1.379(4) . ? C1 C3 1.364(4) . ? C1 C4 1.501(4) . ? C2 H2 0.9500 . ? C2 C7 1.383(5) . ? C3 H3 0.9500 . ? C3 C5 1.381(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7 0.9500 . ? C7 C6 1.358(7) . ? C6 H6 0.9500 . ? C6 C5 1.360(7) . ? C5 H5 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 O001 C00G C00K C00P 132.4(2) . . . . ? O001 C00G C00K C00Q 13.1(3) . . . . ? O001 C00G C00K C00X -106.9(3) . . . . ? N006 N008 C00C O004 168.72(19) . . . . ? N006 N008 C00C O005 -13.9(4) . . . . ? N007 C00D C00F N006 -1.5(3) . . . . ? N007 C00D C00F C00A 177.0(2) . . . . ? N007 C00D C00I C00E -177.7(2) . . . . ? N007 C00G C00K C00P -48.2(3) . . . . ? N007 C00G C00K C00Q -167.5(2) . . . . ? N007 C00G C00K C00X 72.5(3) . . . . ? N008 N006 C009 O002 -178.70(19) . . . . ? N008 N006 C009 O003 0.8(3) . . . . ? N008 N006 C00F C00A 79.2(3) . . . . ? N008 N006 C00F C00D -102.3(2) . . . . ? C009 O002 C00Z C00T 144.9(3) . . . . ? C009 N006 N008 C00C -76.3(3) . . . . ? C009 N006 C00F C00A -101.4(3) . . . . ? C009 N006 C00F C00D 77.1(3) . . . . ? N00B C00E C00I C00D 176.3(2) . . . . ? N00B C00E C00J C00A -176.5(2) . . . . ? C00C O004 C4 C1 -173.9(2) . . . . ? C00D N007 C00G O001 -4.6(4) . . . . ? C00D N007 C00G C00K 176.0(2) . . . . ? C00F N006 N008 C00C 103.1(2) . . . . ? C00F N006 C009 O002 1.9(3) . . . . ? C00F N006 C009 O003 -178.6(2) . . . . ? C00F C00A C00J C00E -1.0(3) . . . . ? C00F C00A C00L C00N 33.3(3) . . . . ? C00F C00A C00L C00R -89.6(3) . . . . ? C00F C00A C00L C00S 152.5(2) . . . . ? C00F C00D C00I C00E 1.6(3) . . . . ? C00G N007 C00D C00F -149.5(2) . . . . ? C00G N007 C00D C00I 29.9(3) . . . . ? C00I C00D C00F N006 179.1(2) . . . . ? C00I C00D C00F C00A -2.3(3) . . . . ? C00I C00E C00J C00A 0.3(4) . . . . ? C00J C00A C00F N006 -179.6(2) . . . . ? C00J C00A C00F C00D 2.0(3) . . . . ? C00J C00A C00L C00N -149.1(2) . . . . ? C00J C00A C00L C00R 88.0(3) . . . . ? C00J C00A C00L C00S -29.9(3) . . . . ? C00J C00E C00I C00D -0.6(3) . . . . ? C00L C00A C00F N006 -1.9(3) . . . . ? C00L C00A C00F C00D 179.6(2) . . . . ? C00L C00A C00J C00E -178.8(2) . . . . ? C00O C00T C00Y C012 -0.6(5) . . . . ? C00O C00T C00Z O002 -7.2(4) . . . . ? C00O C010 C014 C012 0.2(6) . . . . ? C00T C00O C010 C014 -0.8(5) . . . . ? C00T C00Y C012 C014 0.0(6) . . . . ? C00Y C00T C00Z O002 173.7(3) . . . . ? C00Y C012 C014 C010 0.2(7) . . . . ? C00Z O002 C009 O003 -0.6(4) . . . . ? C00Z O002 C009 N006 179.0(2) . . . . ? C00Z C00T C00Y C012 178.5(3) . . . . ? C010 C00O C00T C00Y 1.0(4) . . . . ? C010 C00O C00T C00Z -178.1(3) . . . . ? C1 C2 C7 C6 -1.0(5) . . . . ? C1 C3 C5 C6 0.4(5) . . . . ? C2 C1 C3 C5 -1.4(4) . . . . ? C2 C1 C4 O004 -95.9(3) . . . . ? C2 C7 C6 C5 0.0(6) . . . . ? C3 C1 C2 C7 1.7(4) . . . . ? C3 C1 C4 O004 86.8(3) . . . . ? C4 O004 C00C O005 7.9(4) . . . . ? C4 O004 C00C N008 -174.8(2) . . . . ? C4 C1 C2 C7 -175.7(3) . . . . ? C4 C1 C3 C5 175.9(3) . . . . ? C7 C6 C5 C3 0.3(6) . . . . ?