#------------------------------------------------------------------------------ #$Date: 2018-01-05 04:36:14 +0200 (Fri, 05 Jan 2018) $ #$Revision: 204731 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548592.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_1548592 loop_ _publ_author_name 'Shi, Yong-gang' 'Wang, Junwei' 'Li, Haijun' 'Hu, Guo-fei' 'Li, Xue' 'Mellerup, Soren K.' 'Wang, Nan' 'Peng, Tai' 'Wang, Suning' _publ_section_title ; A Simple Multi-Responsive System Based on Aldehyde Functionalized Amino-Boranes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C7SC03617E _journal_year 2018 _chemical_formula_sum 'C3.09 H3.66 B0.11 N0.11 O0.11' _chemical_formula_weight 45.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-08-14 deposited with the CCDC. 2018-01-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.199(2) _cell_angle_gamma 90 _cell_formula_units_Z 35 _cell_length_a 12.3452(6) _cell_length_b 9.0371(5) _cell_length_c 20.4924(10) _cell_measurement_reflns_used 9929 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 29.89 _cell_measurement_theta_min 2.46 _cell_volume 2285.7(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_unetI/netI 0.0677 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 43562 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.508 _diffrn_reflns_theta_min 2.463 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.155 _exptl_crystal_description block _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.278 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 279 _refine_ls_number_reflns 6954 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0610 _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^)+(0.0700P)^2^+0.6670P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1538 _refine_ls_wR_factor_ref 0.1686 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4901 _reflns_number_total 6954 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc03617e2.cif _cod_data_source_block sy10 _cod_database_code 1548592 _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 0.979 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; sy10.res created by SHELXL-2014/7 TITL mo_WSN_DA1_0m_a.res in P2(1)/n REM Old TITL mo_WSN_DA1_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.145, Rweak 0.006, Alpha 0.027, Orientation as input REM Formula found by SHELXT: C28 N O CELL 0.71073 12.3452 9.0371 20.4924 90.000 91.199 90.000 ZERR 35.000 0.0006 0.0005 0.0010 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H B N O UNIT 108 128 4 4 4 ACTA TEMP -93.150 SIZE 0.22 0.23 0.32 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 10 REM ##### WGHT 0.070000 0.667000 FVAR 0.83271 B1 3 0.702411 0.324598 0.433805 11.00000 0.02648 0.02336 = 0.01954 -0.00198 0.00091 0.00055 O1 5 0.756959 0.586482 0.607826 11.00000 0.08395 0.03140 = 0.04053 -0.01431 -0.01895 0.00719 N1 4 0.839401 0.061558 0.680209 11.00000 0.04713 0.02975 = 0.02746 0.00623 -0.00832 0.00094 C1 1 0.730051 0.506686 0.563313 11.00000 0.04041 0.02547 = 0.02337 -0.00282 -0.00126 0.00427 AFIX 43 H1 2 0.692233 0.550162 0.527301 11.00000 -1.20000 AFIX 0 C2 1 0.751702 0.345448 0.560668 11.00000 0.02639 0.02184 = 0.02058 -0.00157 -0.00026 -0.00066 C3 1 0.730125 0.262587 0.503090 11.00000 0.02734 0.02252 = 0.02008 -0.00105 -0.00004 -0.00257 C4 1 0.746720 0.108967 0.509608 11.00000 0.03386 0.02272 = 0.02339 -0.00220 0.00035 -0.00309 AFIX 43 H4 2 0.730170 0.047686 0.473075 11.00000 -1.20000 AFIX 0 C5 1 0.785519 0.042598 0.565846 11.00000 0.03523 0.02155 = 0.02719 0.00169 0.00035 -0.00154 AFIX 43 H5 2 0.798738 -0.060961 0.566242 11.00000 -1.20000 AFIX 0 C6 1 0.805910 0.126190 0.622865 11.00000 0.02617 0.02728 = 0.02366 0.00408 -0.00100 -0.00217 C7 1 0.787287 0.279841 0.618492 11.00000 0.02917 0.02676 = 0.01969 -0.00239 -0.00272 -0.00054 AFIX 43 H7 2 0.799377 0.339870 0.655998 11.00000 -1.20000 AFIX 0 C8 1 0.870473 0.149485 0.736441 11.00000 0.05291 0.04678 = 0.02685 0.00013 -0.01037 0.00775 AFIX 137 H8A 2 0.930606 0.214841 0.725175 11.00000 -1.50000 H8B 2 0.893270 0.084032 0.772299 11.00000 -1.50000 H8C 2 0.808617 0.209216 0.749985 11.00000 -1.50000 AFIX 0 C9 1 0.858194 -0.095882 0.683557 11.00000 0.06311 0.03242 = 0.04493 0.01542 -0.00899 -0.00167 AFIX 137 H9A 2 0.794018 -0.148455 0.666767 11.00000 -1.50000 H9B 2 0.872536 -0.124749 0.729018 11.00000 -1.50000 H9C 2 0.920794 -0.121365 0.657158 11.00000 -1.50000 AFIX 0 C10 1 0.749930 0.479862 0.413501 11.00000 0.02859 0.02461 = 0.01742 -0.00164 -0.00209 -0.00149 C11 1 0.681410 0.597152 0.393343 11.00000 0.02958 0.02675 = 0.01893 -0.00069 -0.00233 0.00098 C12 1 0.560886 0.574769 0.384032 11.00000 0.02954 0.03537 = 0.04227 -0.00216 -0.00600 0.00365 AFIX 137 H12A 2 0.525460 0.670960 0.377905 11.00000 -1.50000 H12B 2 0.531936 0.525969 0.422652 11.00000 -1.50000 H12C 2 0.547027 0.512848 0.345495 11.00000 -1.50000 AFIX 0 C13 1 0.724266 0.737139 0.382218 11.00000 0.03586 0.02579 = 0.02368 0.00258 0.00171 0.00310 AFIX 43 H13 2 0.676628 0.816377 0.371378 11.00000 -1.20000 AFIX 0 C14 1 0.834934 0.763790 0.386577 11.00000 0.03887 0.02516 = 0.02547 0.00248 0.00483 -0.00246 C15 1 0.880717 0.913631 0.370724 11.00000 0.04912 0.02942 = 0.05883 0.00874 0.01318 -0.00531 AFIX 137 H15A 2 0.910936 0.911664 0.326889 11.00000 -1.50000 H15B 2 0.937975 0.938787 0.402665 11.00000 -1.50000 H15C 2 0.823045 0.987984 0.372296 11.00000 -1.50000 AFIX 0 C16 1 0.902764 0.646882 0.403510 11.00000 0.03071 0.02906 = 0.02664 0.00020 0.00162 -0.00500 AFIX 43 H16 2 0.978814 0.662961 0.405354 11.00000 -1.20000 AFIX 0 C17 1 0.862901 0.506810 0.417877 11.00000 0.02737 0.02568 = 0.02028 0.00029 -0.00284 -0.00142 C18 1 0.943146 0.385921 0.434662 11.00000 0.02929 0.03152 = 0.03584 0.00233 -0.00401 0.00161 AFIX 137 H18A 2 0.921492 0.294362 0.412331 11.00000 -1.50000 H18B 2 0.944635 0.369527 0.481945 11.00000 -1.50000 H18C 2 1.015404 0.415398 0.420607 11.00000 -1.50000 AFIX 0 C19 1 0.632818 0.226068 0.385422 11.00000 0.02861 0.02177 = 0.01865 -0.00070 -0.00149 -0.00185 C21 1 0.667805 0.195310 0.321509 11.00000 0.03197 0.02277 = 0.01885 0.00099 -0.00075 -0.00107 C22 1 0.769987 0.260134 0.294270 11.00000 0.04572 0.04235 = 0.02215 -0.00377 0.00746 -0.01319 AFIX 137 H22A 2 0.788662 0.207296 0.254287 11.00000 -1.50000 H22B 2 0.829283 0.250139 0.326515 11.00000 -1.50000 H22C 2 0.758398 0.365083 0.284312 11.00000 -1.50000 AFIX 0 C23 1 0.608702 0.100075 0.281142 11.00000 0.03641 0.02587 = 0.01993 -0.00390 -0.00269 0.00185 AFIX 43 H23 2 0.634206 0.079642 0.238662 11.00000 -1.20000 AFIX 0 C24 1 0.513753 0.034169 0.301076 11.00000 0.03317 0.02430 = 0.02992 -0.00530 -0.00796 0.00000 C25 1 0.451581 -0.071078 0.257165 11.00000 0.04748 0.04450 = 0.04432 -0.01636 -0.00967 -0.00975 AFIX 137 H25A 2 0.453096 -0.035046 0.212088 11.00000 -1.50000 H25B 2 0.376342 -0.077179 0.271257 11.00000 -1.50000 H25C 2 0.484906 -0.169398 0.259619 11.00000 -1.50000 AFIX 0 C26 1 0.476921 0.067927 0.362919 11.00000 0.02651 0.02800 = 0.03298 -0.00332 -0.00139 -0.00400 AFIX 43 H26 2 0.410822 0.025814 0.376894 11.00000 -1.20000 AFIX 0 C27 1 0.534258 0.161779 0.404940 11.00000 0.02832 0.02454 = 0.02481 -0.00132 -0.00046 -0.00101 C28 1 0.483965 0.197429 0.469768 11.00000 0.03315 0.03866 = 0.03089 -0.00663 0.00708 -0.00465 AFIX 137 H28A 2 0.496922 0.301712 0.480475 11.00000 -1.50000 H28B 2 0.516603 0.134749 0.503892 11.00000 -1.50000 H28C 2 0.405790 0.178921 0.466932 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_WSN_DA1_0m_a.res in P2(1)/n REM R1 = 0.0610 for 4901 Fo > 4sig(Fo) and 0.0913 for all 6954 data REM 279 parameters refined using 0 restraints END WGHT 0.0720 0.6984 REM Highest difference peak 0.278, deepest hole -0.261, 1-sigma level 0.053 Q1 1 0.7024 0.3205 0.4773 11.00000 0.05 0.28 Q2 1 0.7509 0.2959 0.5327 11.00000 0.05 0.26 Q3 1 0.4124 -0.1447 0.2907 11.00000 0.05 0.26 Q4 1 0.3730 0.0016 0.2331 11.00000 0.05 0.25 Q5 1 0.6581 0.2824 0.4086 11.00000 0.05 0.24 Q6 1 0.7626 0.0946 0.5422 11.00000 0.05 0.24 Q7 1 0.7241 0.5402 0.3964 11.00000 0.05 0.24 Q8 1 0.6247 0.5830 0.3882 11.00000 0.05 0.24 Q9 1 0.7191 0.4224 0.4267 11.00000 0.05 0.22 Q10 1 0.9195 0.2684 0.4546 11.00000 0.05 0.22 ; _shelx_res_checksum 11239 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp B1 B 0.70241(13) 0.32460(17) 0.43380(7) 0.0231(3) Uani 1 1 d . . O1 O 0.75696(12) 0.58648(13) 0.60783(6) 0.0522(4) Uani 1 1 d . . N1 N 0.83940(12) 0.06156(15) 0.68021(6) 0.0349(3) Uani 1 1 d . . C1 C 0.73005(13) 0.50669(16) 0.56331(7) 0.0298(3) Uani 1 1 d . . H1 H 0.6922 0.5502 0.5273 0.036 Uiso 1 1 calc R U C2 C 0.75170(11) 0.34545(15) 0.56067(6) 0.0229(3) Uani 1 1 d . . C3 C 0.73013(11) 0.26259(15) 0.50309(6) 0.0233(3) Uani 1 1 d . . C4 C 0.74672(12) 0.10897(15) 0.50961(7) 0.0267(3) Uani 1 1 d . . H4 H 0.7302 0.0477 0.4731 0.032 Uiso 1 1 calc R U C5 C 0.78552(12) 0.04260(16) 0.56585(7) 0.0280(3) Uani 1 1 d . . H5 H 0.7987 -0.0610 0.5662 0.034 Uiso 1 1 calc R U C6 C 0.80591(11) 0.12619(16) 0.62286(7) 0.0257(3) Uani 1 1 d . . C7 C 0.78729(11) 0.27984(16) 0.61849(7) 0.0253(3) Uani 1 1 d . . H7 H 0.7994 0.3399 0.6560 0.030 Uiso 1 1 calc R U C8 C 0.87047(16) 0.1495(2) 0.73644(8) 0.0423(4) Uani 1 1 d . . H8A H 0.9306 0.2148 0.7252 0.064 Uiso 1 1 calc R U H8B H 0.8933 0.0840 0.7723 0.064 Uiso 1 1 calc R U H8C H 0.8086 0.2092 0.7500 0.064 Uiso 1 1 calc R U C9 C 0.85819(17) -0.09588(19) 0.68356(9) 0.0470(5) Uani 1 1 d . . H9A H 0.7940 -0.1485 0.6668 0.070 Uiso 1 1 calc R U H9B H 0.8725 -0.1247 0.7290 0.070 Uiso 1 1 calc R U H9C H 0.9208 -0.1214 0.6572 0.070 Uiso 1 1 calc R U C10 C 0.74993(11) 0.47986(15) 0.41350(6) 0.0236(3) Uani 1 1 d . . C11 C 0.68141(11) 0.59715(15) 0.39334(6) 0.0251(3) Uani 1 1 d . . C12 C 0.56089(12) 0.57477(19) 0.38403(8) 0.0358(4) Uani 1 1 d . . H12A H 0.5255 0.6710 0.3779 0.054 Uiso 1 1 calc R U H12B H 0.5319 0.5260 0.4227 0.054 Uiso 1 1 calc R U H12C H 0.5470 0.5128 0.3455 0.054 Uiso 1 1 calc R U C13 C 0.72427(12) 0.73714(16) 0.38222(7) 0.0284(3) Uani 1 1 d . . H13 H 0.6766 0.8164 0.3714 0.034 Uiso 1 1 calc R U C14 C 0.83493(13) 0.76379(16) 0.38658(7) 0.0298(3) Uani 1 1 d . . C15 C 0.88072(16) 0.91363(19) 0.37072(10) 0.0456(4) Uani 1 1 d . . H15A H 0.9109 0.9117 0.3269 0.068 Uiso 1 1 calc R U H15B H 0.9380 0.9388 0.4027 0.068 Uiso 1 1 calc R U H15C H 0.8230 0.9880 0.3723 0.068 Uiso 1 1 calc R U C16 C 0.90276(12) 0.64688(16) 0.40351(7) 0.0288(3) Uani 1 1 d . . H16 H 0.9788 0.6630 0.4054 0.035 Uiso 1 1 calc R U C17 C 0.86290(11) 0.50681(15) 0.41788(6) 0.0245(3) Uani 1 1 d . . C18 C 0.94315(12) 0.38592(17) 0.43466(8) 0.0323(3) Uani 1 1 d . . H18A H 0.9215 0.2944 0.4123 0.048 Uiso 1 1 calc R U H18B H 0.9446 0.3695 0.4819 0.048 Uiso 1 1 calc R U H18C H 1.0154 0.4154 0.4206 0.048 Uiso 1 1 calc R U C19 C 0.63282(11) 0.22607(15) 0.38542(6) 0.0230(3) Uani 1 1 d . . C21 C 0.66780(12) 0.19531(15) 0.32151(6) 0.0245(3) Uani 1 1 d . . C22 C 0.76999(14) 0.2601(2) 0.29427(7) 0.0366(4) Uani 1 1 d . . H22A H 0.7887 0.2073 0.2543 0.055 Uiso 1 1 calc R U H22B H 0.8293 0.2501 0.3265 0.055 Uiso 1 1 calc R U H22C H 0.7584 0.3651 0.2843 0.055 Uiso 1 1 calc R U C23 C 0.60870(12) 0.10007(15) 0.28114(7) 0.0274(3) Uani 1 1 d . . H23 H 0.6342 0.0796 0.2387 0.033 Uiso 1 1 calc R U C24 C 0.51375(12) 0.03417(16) 0.30108(7) 0.0293(3) Uani 1 1 d . . C25 C 0.45158(15) -0.0711(2) 0.25717(9) 0.0456(4) Uani 1 1 d . . H25A H 0.4531 -0.0350 0.2121 0.068 Uiso 1 1 calc R U H25B H 0.3763 -0.0772 0.2713 0.068 Uiso 1 1 calc R U H25C H 0.4849 -0.1694 0.2596 0.068 Uiso 1 1 calc R U C26 C 0.47692(12) 0.06793(16) 0.36292(7) 0.0292(3) Uani 1 1 d . . H26 H 0.4108 0.0258 0.3769 0.035 Uiso 1 1 calc R U C27 C 0.53426(11) 0.16178(16) 0.40494(7) 0.0259(3) Uani 1 1 d . . C28 C 0.48396(13) 0.19743(19) 0.46977(8) 0.0341(3) Uani 1 1 d . . H28A H 0.4969 0.3017 0.4805 0.051 Uiso 1 1 calc R U H28B H 0.5166 0.1347 0.5039 0.051 Uiso 1 1 calc R U H28C H 0.4058 0.1789 0.4669 0.051 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 B1 0.0265(7) 0.0234(7) 0.0195(7) -0.0020(6) 0.0009(5) 0.0005(6) O1 0.0840(10) 0.0314(6) 0.0405(7) -0.0143(5) -0.0190(7) 0.0072(6) N1 0.0471(8) 0.0298(7) 0.0275(6) 0.0062(5) -0.0083(5) 0.0009(6) C1 0.0404(8) 0.0255(7) 0.0234(7) -0.0028(5) -0.0013(6) 0.0043(6) C2 0.0264(6) 0.0218(6) 0.0206(6) -0.0016(5) -0.0003(5) -0.0007(5) C3 0.0273(7) 0.0225(6) 0.0201(6) -0.0010(5) 0.0000(5) -0.0026(5) C4 0.0339(7) 0.0227(6) 0.0234(6) -0.0022(5) 0.0004(5) -0.0031(6) C5 0.0352(8) 0.0215(6) 0.0272(7) 0.0017(5) 0.0003(5) -0.0015(6) C6 0.0262(7) 0.0273(7) 0.0237(6) 0.0041(5) -0.0010(5) -0.0022(5) C7 0.0292(7) 0.0268(7) 0.0197(6) -0.0024(5) -0.0027(5) -0.0005(5) C8 0.0529(10) 0.0468(10) 0.0268(8) 0.0001(7) -0.0104(7) 0.0078(8) C9 0.0631(12) 0.0324(9) 0.0449(10) 0.0154(7) -0.0090(9) -0.0017(8) C10 0.0286(7) 0.0246(6) 0.0174(6) -0.0016(5) -0.0021(5) -0.0015(5) C11 0.0296(7) 0.0268(7) 0.0189(6) -0.0007(5) -0.0023(5) 0.0010(6) C12 0.0295(8) 0.0354(8) 0.0423(9) -0.0022(7) -0.0060(6) 0.0037(6) C13 0.0359(8) 0.0258(7) 0.0237(7) 0.0026(5) 0.0017(5) 0.0031(6) C14 0.0389(8) 0.0252(7) 0.0255(7) 0.0025(6) 0.0048(6) -0.0025(6) C15 0.0491(10) 0.0294(8) 0.0588(12) 0.0087(8) 0.0132(8) -0.0053(7) C16 0.0307(7) 0.0291(7) 0.0266(7) 0.0002(6) 0.0016(5) -0.0050(6) C17 0.0274(7) 0.0257(7) 0.0203(6) 0.0003(5) -0.0028(5) -0.0014(5) C18 0.0293(7) 0.0315(8) 0.0358(8) 0.0023(6) -0.0040(6) 0.0016(6) C19 0.0286(7) 0.0218(6) 0.0187(6) -0.0007(5) -0.0015(5) -0.0019(5) C21 0.0320(7) 0.0228(6) 0.0188(6) 0.0010(5) -0.0008(5) -0.0011(5) C22 0.0457(9) 0.0424(9) 0.0221(7) -0.0038(6) 0.0075(6) -0.0132(7) C23 0.0364(8) 0.0259(7) 0.0199(6) -0.0039(5) -0.0027(5) 0.0019(6) C24 0.0332(8) 0.0243(7) 0.0299(7) -0.0053(6) -0.0080(6) 0.0000(6) C25 0.0475(10) 0.0445(10) 0.0443(10) -0.0164(8) -0.0097(8) -0.0098(8) C26 0.0265(7) 0.0280(7) 0.0330(8) -0.0033(6) -0.0014(6) -0.0040(6) C27 0.0283(7) 0.0245(6) 0.0248(7) -0.0013(5) -0.0005(5) -0.0010(5) C28 0.0332(8) 0.0387(9) 0.0309(8) -0.0066(6) 0.0071(6) -0.0047(7) 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' O O 0.0106 0.0060 '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 C3 B1 C19 118.50(12) C3 B1 C10 118.94(12) C19 B1 C10 122.49(12) C6 N1 C9 120.47(14) C6 N1 C8 121.36(13) C9 N1 C8 117.68(13) O1 C1 C2 124.69(14) O1 C1 H1 117.7 C2 C1 H1 117.7 C7 C2 C3 122.37(13) C7 C2 C1 116.27(12) C3 C2 C1 121.23(12) C4 C3 C2 114.64(12) C4 C3 B1 118.00(12) C2 C3 B1 127.03(12) C5 C4 C3 123.78(13) C5 C4 H4 118.1 C3 C4 H4 118.1 C4 C5 C6 120.90(13) C4 C5 H5 119.6 C6 C5 H5 119.6 N1 C6 C5 121.91(13) N1 C6 C7 121.39(13) C5 C6 C7 116.68(12) C2 C7 C6 121.54(13) C2 C7 H7 119.2 C6 C7 H7 119.2 N1 C8 H8A 109.5 N1 C8 H8B 109.5 H8A C8 H8B 109.5 N1 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 N1 C9 H9A 109.5 N1 C9 H9B 109.5 H9A C9 H9B 109.5 N1 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C11 C10 C17 118.18(13) C11 C10 B1 121.34(12) C17 C10 B1 120.43(12) C13 C11 C10 120.17(13) C13 C11 C12 118.56(13) C10 C11 C12 121.27(13) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C14 C13 C11 121.60(14) C14 C13 H13 119.2 C11 C13 H13 119.2 C16 C14 C13 118.16(14) C16 C14 C15 120.76(15) C13 C14 C15 121.04(14) C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C14 C16 C17 122.08(14) C14 C16 H16 119.0 C17 C16 H16 119.0 C16 C17 C10 119.66(13) C16 C17 C18 118.24(13) C10 C17 C18 122.04(13) C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C27 C19 C21 117.53(12) C27 C19 B1 121.06(12) C21 C19 B1 121.39(12) C23 C21 C19 120.38(13) C23 C21 C22 116.93(12) C19 C21 C22 122.68(13) C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C24 C23 C21 121.87(13) C24 C23 H23 119.1 C21 C23 H23 119.1 C23 C24 C26 118.04(13) C23 C24 C25 121.26(14) C26 C24 C25 120.70(14) C24 C25 H25A 109.5 C24 C25 H25B 109.5 H25A C25 H25B 109.5 C24 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C24 C26 C27 121.76(14) C24 C26 H26 119.1 C27 C26 H26 119.1 C26 C27 C19 120.34(13) C26 C27 C28 117.41(13) C19 C27 C28 122.17(13) C27 C28 H28A 109.5 C27 C28 H28B 109.5 H28A C28 H28B 109.5 C27 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance B1 C3 1.558(2) B1 C19 1.574(2) B1 C10 1.580(2) O1 C1 1.2041(18) N1 C6 1.3685(18) N1 C9 1.443(2) N1 C8 1.445(2) C1 C2 1.483(2) C1 H1 0.9500 C2 C7 1.3881(19) C2 C3 1.4180(18) C3 C4 1.4092(19) C4 C5 1.376(2) C4 H4 0.9500 C5 C6 1.410(2) C5 H5 0.9500 C6 C7 1.410(2) C7 H7 0.9500 C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 C10 C11 1.4125(19) C10 C17 1.4168(19) C11 C13 1.392(2) C11 C12 1.510(2) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C14 1.388(2) C13 H13 0.9500 C14 C16 1.388(2) C14 C15 1.505(2) C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 C17 1.392(2) C16 H16 0.9500 C17 C18 1.510(2) C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 C27 1.4136(19) C19 C21 1.4152(18) C21 C23 1.3900(19) C21 C22 1.508(2) C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 C24 1.384(2) C23 H23 0.9500 C24 C26 1.389(2) C24 C25 1.508(2) C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 C26 C27 1.3916(19) C26 H26 0.9500 C27 C28 1.513(2) C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800