#------------------------------------------------------------------------------ #$Date: 2024-04-23 04:13:16 +0300 (Tue, 23 Apr 2024) $ #$Revision: 291331 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159913.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_7159913 loop_ _publ_author_name 'Alexeev, Michael S.' 'Strelkova, Tatyana V.' 'Ilyin, Jr., Michail M.' 'Nelyubina, Yulia V.' 'Bespalov, Ivan A.' 'Medvedev, Michael' 'Khrustalev, Victor N.' 'Kuznetsov, Nikolai' _publ_section_title ; New Generation of Highly Reactive Allylborating Agents For Cu(I)-Catalyzed Allylation of Chiral Sulfinylimines ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00291A _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C15 H27 B N2' _chemical_formula_sum 'C15 H27 B N2' _chemical_formula_weight 246.19 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2023-08-14 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2023-08-16 deposited with the CCDC. 2024-04-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6952(2) _cell_length_b 10.1193(2) _cell_length_c 17.1397(4) _cell_measurement_reflns_used 5580 _cell_measurement_temperature 100 _cell_measurement_theta_max 28.84 _cell_measurement_theta_min 2.34 _cell_volume 1508.11(6) _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker Quest D8' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_unetI/netI 0.0352 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 20204 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.993 _diffrn_reflns_theta_min 2.337 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_T_max 0.4330 _exptl_absorpt_correction_T_min 0.3775 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1112 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.8718. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.084 _exptl_crystal_description needle _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.208 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details ; Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -1.4(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 4000 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0485 _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^)+(0.0608P)^2^+0.2999P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1193 _refine_ls_wR_factor_ref 0.1240 _reflns_Friedel_coverage 0.749 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3582 _reflns_number_total 4000 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00291a3.cif _cod_data_source_block TABDABCO _cod_database_code 7159913 _shelxl_version_number 2014/6 _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 0.997 _shelx_estimated_absorpt_t_min 0.978 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups 2. Restrained distances C14-C13 \\sim C14'-C13' with sigma of 0.02 C13'-B1 \\sim C13-B1 with sigma of 0.02 C10'-B1 \\sim C10-B1 with sigma of 0.02 C11'-C10' \\sim C11-C10 with sigma of 0.02 C12'-C11' \\sim C12-C11 with sigma of 0.02 C14-C15 \\sim C14'-C15 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C13) = Uanis(C13') Uanis(C14) = Uanis(C14') Uanis(C10') = Uanis(C10) Uanis(C11) = Uanis(C11') Uanis(C12') = Uanis(C12) 4. Others Sof(H15C)=Sof(H15D)=Sof(C13')=Sof(H13C)=Sof(H13D)=Sof(C14')=Sof(H14')=1-FVAR(1) Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=FVAR(1) Sof(C10')=Sof(H10C)=Sof(H10D)=Sof(C11')=Sof(H11')=Sof(C12')=Sof(H12C)= Sof(H12D)=1-FVAR(2) Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)= FVAR(2) 5.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C10'(H10C,H10D), C13'(H13C,H13D) 5.b Aromatic/amide H refined with riding coordinates: C8(H8), C11(H11), C14(H14), C11'(H11'), C14'(H14') 5.c X=CH2 refined with riding coordinates: C9(H9A,H9B), C15(H15A,H15B), C15(H15C,H15D), C12(H12A,H12B), C12'(H12C,H12D) ; _shelx_res_file ; TITL a_a.res in P2(1)2(1)2(1) REM Old TITL a in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.159, Rweak 0.044, Alpha 0.002, Orientation as input REM Flack x = -0.308 ( 0.891 ) from Parsons' quotients REM Formula found by SHELXT: C14 N4 CELL 0.71073 8.6952 10.1193 17.1397 90 90 90 ZERR 4 0.0002 0.0002 0.0004 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 B N UNIT 60 108 4 8 SADI C14 C13 C14' C13' EADP C13 C13' EADP C14 C14' SADI C13' B1 C13 B1 EADP C10' C10 SADI C10' B1 C10 B1 EADP C11 C11' SADI C11' C10' C11 C10 SADI C12' C11' C12 C11 EADP C12' C12 SADI C14 C15 C14' C15 L.S. 10 PLAN 5 SIZE 0.05 0.05 0.35 TEMP -173.15 CONF MORE -1 BOND $H fmap 2 acta OMIT -4 58 REM REM REM WGHT 0.060800 0.299900 FVAR 0.98415 0.77402 0.76762 N1 4 0.223287 0.447188 0.601773 11.00000 0.02016 0.02152 = 0.02367 -0.00652 0.00124 -0.00033 N2 4 0.024883 0.306551 0.522298 11.00000 0.02588 0.02970 = 0.02957 -0.01053 -0.00011 -0.00519 C1 1 0.239390 0.302360 0.618256 11.00000 0.03350 0.02099 = 0.03636 -0.00586 -0.00575 0.00254 AFIX 23 H1A 2 0.234860 0.286999 0.675254 11.00000 -1.20000 H1B 2 0.340353 0.270805 0.599132 11.00000 -1.20000 AFIX 0 C2 1 0.110572 0.225295 0.578026 11.00000 0.03618 0.02782 = 0.04439 -0.00091 -0.00451 -0.01090 AFIX 23 H2A 2 0.155418 0.148597 0.550309 11.00000 -1.20000 H2B 2 0.038793 0.191078 0.618053 11.00000 -1.20000 AFIX 0 C3 1 0.244738 0.463919 0.515001 11.00000 0.03160 0.03681 = 0.02246 -0.00781 0.00494 -0.00965 AFIX 23 H3A 2 0.352953 0.445045 0.500923 11.00000 -1.20000 H3B 2 0.221678 0.556316 0.500049 11.00000 -1.20000 AFIX 0 C4 1 0.137719 0.369701 0.470713 11.00000 0.03841 0.03861 = 0.02638 -0.00524 -0.00309 -0.01149 AFIX 23 H4A 2 0.082742 0.419608 0.429602 11.00000 -1.20000 H4B 2 0.200130 0.300553 0.444883 11.00000 -1.20000 AFIX 0 C5 1 0.060895 0.485509 0.619913 11.00000 0.01891 0.02649 = 0.03025 -0.00888 -0.00012 0.00133 AFIX 23 H5A 2 0.048240 0.581965 0.612701 11.00000 -1.20000 H5B 2 0.037689 0.464278 0.675054 11.00000 -1.20000 AFIX 0 C6 1 -0.051440 0.411869 0.566573 11.00000 0.02285 0.04955 = 0.05275 -0.02719 -0.00530 -0.00044 AFIX 23 H6A 2 -0.134765 0.373036 0.598568 11.00000 -1.20000 H6B 2 -0.098639 0.475379 0.529736 11.00000 -1.20000 AFIX 0 C7 1 0.518587 0.469527 0.644286 11.00000 0.02189 0.03153 = 0.03956 -0.01326 -0.00317 0.00347 AFIX 23 H7A 2 0.517222 0.382293 0.670424 11.00000 -1.20000 H7B 2 0.539137 0.454492 0.588171 11.00000 -1.20000 AFIX 0 C8 1 0.646121 0.550630 0.677846 11.00000 0.02106 0.03129 = 0.03384 -0.00729 0.00050 0.00062 AFIX 43 H8 2 0.673327 0.628419 0.650054 11.00000 -1.20000 AFIX 0 C9 1 0.724399 0.525862 0.741521 11.00000 0.03780 0.04101 = 0.05669 -0.00119 -0.01676 0.00241 AFIX 93 H9A 2 0.701898 0.449351 0.771542 11.00000 -1.20000 H9B 2 0.803650 0.584418 0.757662 11.00000 -1.20000 AFIX 0 C15 1 0.143412 0.403168 0.830803 11.00000 0.05617 0.03964 = 0.02815 0.00222 0.00038 0.00357 PART 1 AFIX 93 H15A 2 0.052473 0.454556 0.825980 21.00000 -1.20000 H15B 2 0.143191 0.325507 0.861944 21.00000 -1.20000 AFIX 93 PART 2 H15C 2 0.194043 0.320290 0.826544 -21.00000 -1.20000 H15D 2 0.052364 0.410804 0.861105 -21.00000 -1.20000 AFIX 0 PART 0 B1 3 0.350344 0.538068 0.653720 11.00000 0.02014 0.02650 = 0.02875 -0.01120 -0.00142 -0.00042 PART 1 C10 1 0.366059 0.688548 0.611166 31.00000 0.02924 0.02122 = 0.02859 -0.00199 -0.00521 -0.00495 AFIX 23 H10A 2 0.445148 0.738561 0.640399 31.00000 -1.20000 H10B 2 0.406903 0.674569 0.557886 31.00000 -1.20000 AFIX 0 C11 1 0.227371 0.776025 0.604063 31.00000 0.03472 0.02089 = 0.03451 -0.00475 -0.00858 -0.00107 AFIX 43 H11 2 0.170568 0.791361 0.650536 31.00000 -1.20000 AFIX 0 C12 1 0.175972 0.833765 0.540409 31.00000 0.03977 0.02583 = 0.04346 0.00070 -0.00646 0.00075 AFIX 93 H12A 2 0.228400 0.821775 0.492298 31.00000 -1.20000 H12B 2 0.086437 0.887442 0.542563 31.00000 -1.20000 AFIX 0 C13 1 0.291567 0.560357 0.742175 21.00000 0.02373 0.02574 = 0.02417 -0.00468 -0.00166 0.00291 AFIX 23 H13A 2 0.363842 0.621913 0.768081 21.00000 -1.20000 H13B 2 0.190295 0.604898 0.739895 21.00000 -1.20000 AFIX 0 C14 1 0.275525 0.441244 0.792660 21.00000 0.02713 0.03133 = 0.02370 -0.00259 -0.00057 0.00771 AFIX 43 H14 2 0.363848 0.387056 0.799057 21.00000 -1.20000 AFIX 0 PART 2 C10' 1 0.313269 0.681904 0.659114 -31.00000 0.02924 0.02122 = 0.02859 -0.00199 -0.00521 -0.00495 AFIX 23 H10C 2 0.378701 0.722984 0.699688 -31.00000 -1.20000 H10D 2 0.204621 0.692487 0.675214 -31.00000 -1.20000 AFIX 0 C11' 1 0.338208 0.752239 0.582910 -31.00000 0.03472 0.02089 = 0.03451 -0.00475 -0.00858 -0.00107 AFIX 43 H11' 2 0.440981 0.749232 0.564186 -31.00000 -1.20000 AFIX 0 C12' 1 0.241541 0.817672 0.537391 -31.00000 0.03977 0.02583 = 0.04346 0.00070 -0.00646 0.00075 AFIX 93 H12C 2 0.136406 0.825512 0.551743 -31.00000 -1.20000 H12D 2 0.277327 0.856775 0.490385 -31.00000 -1.20000 AFIX 0 C13' 1 0.337257 0.474347 0.752285 -21.00000 0.02373 0.02574 = 0.02417 -0.00468 -0.00166 0.00291 AFIX 23 H13C 2 0.353618 0.377628 0.749715 -21.00000 -1.20000 H13D 2 0.424096 0.511850 0.782371 -21.00000 -1.20000 AFIX 0 C14' 1 0.194275 0.497853 0.798028 -21.00000 0.02713 0.03133 = 0.02370 -0.00259 -0.00057 0.00771 AFIX 43 H14' 2 0.146759 0.582243 0.800966 -21.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in P2(1)2(1)2(1) REM R1 = 0.0485 for 3582 Fo > 4sig(Fo) and 0.0557 for all 4000 data REM 180 parameters refined using 6 restraints END WGHT 0.0610 0.3011 REM Highest difference peak 0.208, deepest hole -0.183, 1-sigma level 0.037 Q1 1 0.6436 0.5516 0.7229 11.00000 0.05 0.21 Q2 1 0.4380 0.4993 0.6570 11.00000 0.05 0.20 Q3 1 0.0003 0.4554 0.5886 11.00000 0.05 0.20 Q4 1 0.3296 0.5135 0.7062 11.00000 0.05 0.19 Q5 1 0.2337 0.8349 0.5091 11.00000 0.05 0.17 ; _shelx_res_checksum 81653 _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 N1 N 0.22329(19) 0.44719(15) 0.60177(9) 0.0218(3) Uani 1 1 d . . . . . N2 N 0.0249(2) 0.30655(18) 0.52230(10) 0.0284(4) Uani 1 1 d . . . . . C1 C 0.2394(3) 0.3024(2) 0.61826(13) 0.0303(5) Uani 1 1 d . . . . . H1A H 0.2349 0.2870 0.6753 0.036 Uiso 1 1 calc R U . . . H1B H 0.3404 0.2708 0.5991 0.036 Uiso 1 1 calc R U . . . C2 C 0.1106(3) 0.2253(2) 0.57803(14) 0.0361(5) Uani 1 1 d . . . . . H2A H 0.1554 0.1486 0.5503 0.043 Uiso 1 1 calc R U . . . H2B H 0.0388 0.1911 0.6181 0.043 Uiso 1 1 calc R U . . . C3 C 0.2447(3) 0.4639(2) 0.51500(11) 0.0303(5) Uani 1 1 d . . . . . H3A H 0.3530 0.4450 0.5009 0.036 Uiso 1 1 calc R U . . . H3B H 0.2217 0.5563 0.5000 0.036 Uiso 1 1 calc R U . . . C4 C 0.1377(3) 0.3697(2) 0.47071(13) 0.0345(5) Uani 1 1 d . . . . . H4A H 0.0827 0.4196 0.4296 0.041 Uiso 1 1 calc R U . . . H4B H 0.2001 0.3006 0.4449 0.041 Uiso 1 1 calc R U . . . C5 C 0.0609(2) 0.4855(2) 0.61991(12) 0.0252(4) Uani 1 1 d . . . . . H5A H 0.0482 0.5820 0.6127 0.030 Uiso 1 1 calc R U . . . H5B H 0.0377 0.4643 0.6751 0.030 Uiso 1 1 calc R U . . . C6 C -0.0514(3) 0.4119(3) 0.56657(16) 0.0417(6) Uani 1 1 d . . . . . H6A H -0.1348 0.3730 0.5986 0.050 Uiso 1 1 calc R U . . . H6B H -0.0986 0.4754 0.5297 0.050 Uiso 1 1 calc R U . . . C7 C 0.5186(2) 0.4695(2) 0.64429(13) 0.0310(5) Uani 1 1 d . . . . . H7A H 0.5172 0.3823 0.6704 0.037 Uiso 1 1 calc R U . . . H7B H 0.5391 0.4545 0.5882 0.037 Uiso 1 1 calc R U . . . C8 C 0.6461(2) 0.5506(2) 0.67785(12) 0.0287(4) Uani 1 1 d . . . . . H8 H 0.6733 0.6284 0.6501 0.034 Uiso 1 1 calc R U . . . C9 C 0.7244(3) 0.5259(3) 0.74152(16) 0.0452(6) Uani 1 1 d . . . . . H9A H 0.7019 0.4494 0.7715 0.054 Uiso 1 1 calc R U . . . H9B H 0.8036 0.5844 0.7577 0.054 Uiso 1 1 calc R U . . . C15 C 0.1434(3) 0.4032(3) 0.83080(13) 0.0413(6) Uani 1 1 d D . . . . H15A H 0.0525 0.4546 0.8260 0.050 Uiso 0.774(3) 1 calc R U P A 1 H15B H 0.1432 0.3255 0.8619 0.050 Uiso 0.774(3) 1 calc R U P A 1 H15C H 0.1940 0.3203 0.8265 0.050 Uiso 0.226(3) 1 calc R U P A 2 H15D H 0.0524 0.4108 0.8611 0.050 Uiso 0.226(3) 1 calc R U P A 2 B1 B 0.3503(3) 0.5381(2) 0.65372(13) 0.0251(4) Uani 1 1 d D . . . . C10 C 0.3661(3) 0.6885(3) 0.61117(16) 0.0263(5) Uani 0.768(3) 1 d D . P A 1 H10A H 0.4451 0.7386 0.6404 0.032 Uiso 0.768(3) 1 calc R U P A 1 H10B H 0.4069 0.6746 0.5579 0.032 Uiso 0.768(3) 1 calc R U P A 1 C11 C 0.2274(4) 0.7760(2) 0.60406(17) 0.0300(6) Uani 0.768(3) 1 d D . P A 1 H11 H 0.1706 0.7914 0.6505 0.036 Uiso 0.768(3) 1 calc R U P A 1 C12 C 0.1760(4) 0.8338(3) 0.5404(2) 0.0364(8) Uani 0.768(3) 1 d D . P A 1 H12A H 0.2284 0.8218 0.4923 0.044 Uiso 0.768(3) 1 calc R U P A 1 H12B H 0.0864 0.8874 0.5426 0.044 Uiso 0.768(3) 1 calc R U P A 1 C13 C 0.2916(3) 0.5604(3) 0.74217(14) 0.0245(5) Uani 0.774(3) 1 d D . P A 1 H13A H 0.3638 0.6219 0.7681 0.029 Uiso 0.774(3) 1 calc R U P A 1 H13B H 0.1903 0.6049 0.7399 0.029 Uiso 0.774(3) 1 calc R U P A 1 C14 C 0.2755(3) 0.4412(3) 0.79266(15) 0.0274(5) Uani 0.774(3) 1 d D . P A 1 H14 H 0.3638 0.3871 0.7991 0.033 Uiso 0.774(3) 1 calc R U P A 1 C10' C 0.3133(11) 0.6819(8) 0.6591(5) 0.0263(5) Uani 0.232(3) 1 d D . P A 2 H10C H 0.3787 0.7230 0.6997 0.032 Uiso 0.232(3) 1 calc R U P A 2 H10D H 0.2046 0.6925 0.6752 0.032 Uiso 0.232(3) 1 calc R U P A 2 C11' C 0.3382(12) 0.7522(9) 0.5829(5) 0.0300(6) Uani 0.232(3) 1 d D . P A 2 H11' H 0.4410 0.7492 0.5642 0.036 Uiso 0.232(3) 1 calc R U P A 2 C12' C 0.2415(15) 0.8177(13) 0.5374(8) 0.0364(8) Uani 0.232(3) 1 d D . P A 2 H12C H 0.1364 0.8255 0.5517 0.044 Uiso 0.232(3) 1 calc R U P A 2 H12D H 0.2773 0.8568 0.4904 0.044 Uiso 0.232(3) 1 calc R U P A 2 C13' C 0.3373(10) 0.4743(9) 0.7523(5) 0.0245(5) Uani 0.226(3) 1 d D . P A 2 H13C H 0.3536 0.3776 0.7497 0.029 Uiso 0.226(3) 1 calc R U P A 2 H13D H 0.4241 0.5119 0.7824 0.029 Uiso 0.226(3) 1 calc R U P A 2 C14' C 0.1943(11) 0.4979(9) 0.7980(5) 0.0274(5) Uani 0.226(3) 1 d D . P A 2 H14' H 0.1468 0.5822 0.8010 0.033 Uiso 0.226(3) 1 calc R U P A 2 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 N1 0.0202(7) 0.0215(7) 0.0237(7) -0.0065(6) 0.0012(6) -0.0003(6) N2 0.0259(9) 0.0297(9) 0.0296(8) -0.0105(7) -0.0001(7) -0.0052(7) C1 0.0335(11) 0.0210(9) 0.0364(10) -0.0059(8) -0.0058(9) 0.0025(8) C2 0.0362(12) 0.0278(11) 0.0444(13) -0.0009(9) -0.0045(10) -0.0109(9) C3 0.0316(11) 0.0368(11) 0.0225(9) -0.0078(8) 0.0049(8) -0.0097(9) C4 0.0384(12) 0.0386(12) 0.0264(10) -0.0052(9) -0.0031(9) -0.0115(10) C5 0.0189(9) 0.0265(9) 0.0302(9) -0.0089(8) -0.0001(7) 0.0013(7) C6 0.0228(11) 0.0496(14) 0.0528(14) -0.0272(12) -0.0053(10) -0.0004(10) C7 0.0219(10) 0.0315(10) 0.0396(11) -0.0133(9) -0.0032(8) 0.0035(8) C8 0.0211(9) 0.0313(10) 0.0338(10) -0.0073(9) 0.0005(8) 0.0006(8) C9 0.0378(13) 0.0410(13) 0.0567(15) -0.0012(11) -0.0168(12) 0.0024(11) C15 0.0562(16) 0.0396(12) 0.0281(10) 0.0022(9) 0.0004(11) 0.0036(12) B1 0.0201(10) 0.0265(11) 0.0288(10) -0.0112(9) -0.0014(8) -0.0004(8) C10 0.0292(14) 0.0212(11) 0.0286(13) -0.0020(11) -0.0052(10) -0.0050(10) C11 0.0347(14) 0.0209(11) 0.0345(13) -0.0047(10) -0.0086(12) -0.0011(11) C12 0.040(2) 0.0258(14) 0.0435(15) 0.0007(11) -0.0065(18) 0.0008(15) C13 0.0237(12) 0.0257(11) 0.0242(11) -0.0047(10) -0.0017(9) 0.0029(9) C14 0.0271(13) 0.0313(13) 0.0237(11) -0.0026(10) -0.0006(10) 0.0077(11) C10' 0.0292(14) 0.0212(11) 0.0286(13) -0.0020(11) -0.0052(10) -0.0050(10) C11' 0.0347(14) 0.0209(11) 0.0345(13) -0.0047(10) -0.0086(12) -0.0011(11) C12' 0.040(2) 0.0258(14) 0.0435(15) 0.0007(11) -0.0065(18) 0.0008(15) C13' 0.0237(12) 0.0257(11) 0.0242(11) -0.0047(10) -0.0017(9) 0.0029(9) C14' 0.0271(13) 0.0313(13) 0.0237(11) -0.0026(10) -0.0006(10) 0.0077(11) 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' B B 0.0013 0.0007 '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' 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 C1 N1 C3 106.50(15) . . ? C1 N1 B1 111.81(15) . . ? C3 N1 B1 112.17(15) . . ? C5 N1 C1 107.59(16) . . ? C5 N1 C3 107.00(16) . . ? C5 N1 B1 111.47(14) . . ? C2 N2 C4 107.30(18) . . ? C2 N2 C6 107.50(18) . . ? C6 N2 C4 107.33(19) . . ? N1 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? N1 C1 C2 110.19(17) . . ? H1A C1 H1B 108.1 . . ? C2 C1 H1A 109.6 . . ? C2 C1 H1B 109.6 . . ? N2 C2 C1 112.37(17) . . ? N2 C2 H2A 109.1 . . ? N2 C2 H2B 109.1 . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N1 C3 H3A 109.6 . . ? N1 C3 H3B 109.6 . . ? N1 C3 C4 110.08(17) . . ? H3A C3 H3B 108.2 . . ? C4 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? N2 C4 C3 112.23(17) . . ? N2 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C3 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? N1 C5 C6 110.59(15) . . ? H5A C5 H5B 108.1 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? N2 C6 C5 111.95(18) . . ? N2 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? C5 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? H7A C7 H7B 107.7 . . ? C8 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C8 C7 B1 113.25(17) . . ? B1 C7 H7A 108.9 . . ? B1 C7 H7B 108.9 . . ? C7 C8 H8 116.5 . . ? C9 C8 C7 126.9(2) . . ? C9 C8 H8 116.5 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? H15A C15 H15B 120.0 . . ? H15C C15 H15D 120.0 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? C14' C15 H15C 120.0 . . ? C14' C15 H15D 120.0 . . ? N1 B1 C10 108.36(16) . . ? N1 B1 C13' 104.9(3) . . ? C7 B1 N1 107.65(15) . . ? C7 B1 C10 105.54(18) . . ? C7 B1 C13' 89.9(3) . . ? C13 B1 N1 111.31(17) . . ? C13 B1 C7 115.92(19) . . ? C13 B1 C10 107.70(18) . . ? C10' B1 N1 114.9(4) . . ? C10' B1 C7 128.0(4) . . ? C10' B1 C13' 106.0(5) . . ? B1 C10 H10A 107.3 . . ? B1 C10 H10B 107.3 . . ? H10A C10 H10B 106.9 . . ? C11 C10 B1 120.0(2) . . ? C11 C10 H10A 107.3 . . ? C11 C10 H10B 107.3 . . ? C10 C11 H11 116.5 . . ? C12 C11 C10 127.0(3) . . ? C12 C11 H11 116.5 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? B1 C13 H13A 107.9 . . ? B1 C13 H13B 107.9 . . ? H13A C13 H13B 107.2 . . ? C14 C13 B1 117.5(2) . . ? C14 C13 H13A 107.9 . . ? C14 C13 H13B 107.9 . . ? C15 C14 C13 125.5(2) . . ? C15 C14 H14 117.3 . . ? C13 C14 H14 117.3 . . ? B1 C10' H10C 109.2 . . ? B1 C10' H10D 109.2 . . ? B1 C10' C11' 112.1(7) . . ? H10C C10' H10D 107.9 . . ? C11' C10' H10C 109.2 . . ? C11' C10' H10D 109.2 . . ? C10' C11' H11' 114.5 . . ? C12' C11' C10' 131.1(11) . . ? C12' C11' H11' 114.5 . . ? C11' C12' H12C 120.0 . . ? C11' C12' H12D 120.0 . . ? H12C C12' H12D 120.0 . . ? B1 C13' H13C 107.5 . . ? B1 C13' H13D 107.5 . . ? H13C C13' H13D 107.0 . . ? C14' C13' B1 119.1(6) . . ? C14' C13' H13C 107.5 . . ? C14' C13' H13D 107.5 . . ? C15 C14' C13' 115.4(8) . . ? C15 C14' H14' 122.3 . . ? C13' C14' H14' 122.3 . . ? 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 N1 C1 1.499(3) . ? N1 C3 1.508(2) . ? N1 C5 1.497(2) . ? N1 B1 1.691(3) . ? N2 C2 1.464(3) . ? N2 C4 1.467(3) . ? N2 C6 1.467(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.529(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.533(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.531(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.495(3) . ? C7 B1 1.627(3) . ? C8 H8 0.9500 . ? C8 C9 1.310(3) . ? C9 H9A 0.9500 . ? C9 H9B 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C15 H15C 0.9500 . ? C15 H15D 0.9500 . ? C15 C14 1.377(4) . ? C15 C14' 1.195(9) . ? B1 C10 1.694(4) . ? B1 C13 1.616(3) . ? B1 C10' 1.494(8) . ? B1 C13' 1.812(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.501(4) . ? C11 H11 0.9500 . ? C11 C12 1.316(5) . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.490(4) . ? C14 H14 0.9500 . ? C10' H10C 0.9900 . ? C10' H10D 0.9900 . ? C10' C11' 1.503(12) . ? C11' H11' 0.9500 . ? C11' C12' 1.324(14) . ? C12' H12C 0.9500 . ? C12' H12D 0.9500 . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C13' C14' 1.489(11) . ? C14' H14' 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 N1 C1 C2 N2 11.4(3) . . . . ? N1 C3 C4 N2 10.2(3) . . . . ? N1 C5 C6 N2 10.5(3) . . . . ? N1 B1 C10 C11 60.5(3) . . . . ? N1 B1 C13 C14 63.9(3) . . . . ? N1 B1 C10' C11' -71.7(7) . . . . ? N1 B1 C13' C14' -68.7(7) . . . . ? C1 N1 C3 C4 51.9(2) . . . . ? C1 N1 C5 C6 -62.7(2) . . . . ? C1 N1 B1 C7 47.8(2) . . . . ? C1 N1 B1 C10 161.46(17) . . . . ? C1 N1 B1 C13 -80.3(2) . . . . ? C1 N1 B1 C10' -162.9(4) . . . . ? C1 N1 B1 C13' -46.9(3) . . . . ? C2 N2 C4 C3 -63.4(2) . . . . ? C2 N2 C6 C5 51.3(3) . . . . ? C3 N1 C1 C2 -64.0(2) . . . . ? C3 N1 C5 C6 51.5(2) . . . . ? C3 N1 B1 C7 -71.8(2) . . . . ? C3 N1 B1 C10 41.9(2) . . . . ? C3 N1 B1 C13 160.14(19) . . . . ? C3 N1 B1 C10' 77.6(4) . . . . ? C3 N1 B1 C13' -166.5(3) . . . . ? C4 N2 C2 C1 51.2(2) . . . . ? C4 N2 C6 C5 -63.9(3) . . . . ? C5 N1 C1 C2 50.5(2) . . . . ? C5 N1 C3 C4 -62.9(2) . . . . ? C5 N1 B1 C7 168.24(17) . . . . ? C5 N1 B1 C10 -78.1(2) . . . . ? C5 N1 B1 C13 40.2(2) . . . . ? C5 N1 B1 C10' -42.4(5) . . . . ? C5 N1 B1 C13' 73.6(3) . . . . ? C6 N2 C2 C1 -64.0(2) . . . . ? C6 N2 C4 C3 51.8(2) . . . . ? C7 B1 C10 C11 175.6(2) . . . . ? C7 B1 C13 C14 -59.5(3) . . . . ? C7 B1 C10' C11' 70.3(8) . . . . ? C7 B1 C13' C14' -177.0(7) . . . . ? C8 C7 B1 N1 171.68(17) . . . . ? C8 C7 B1 C10 56.1(2) . . . . ? C8 C7 B1 C13 -63.0(3) . . . . ? C8 C7 B1 C10' 27.6(5) . . . . ? C8 C7 B1 C13' -82.8(3) . . . . ? B1 N1 C1 C2 173.18(17) . . . . ? B1 N1 C3 C4 174.54(17) . . . . ? B1 N1 C5 C6 174.42(18) . . . . ? B1 C7 C8 C9 108.1(3) . . . . ? B1 C10 C11 C12 -128.2(3) . . . . ? B1 C13 C14 C15 -123.9(3) . . . . ? B1 C10' C11' C12' 119.2(12) . . . . ? B1 C13' C14' C15 133.0(7) . . . . ? C10 B1 C13 C14 -177.4(2) . . . . ? C13 B1 C10 C11 -60.0(3) . . . . ? C10' B1 C13' C14' 53.2(8) . . . . ? C13' B1 C10' C11' 173.0(6) . . . . ?