#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:10:21 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267226 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158100.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_7158100 loop_ _publ_author_name 'Chen, Rongxiang' 'Jia, Ruo-Ling' 'Li, Wenbo' 'Zhao, Wei' 'Wang, Kai-Kai' 'Wang, Zhan-Yong' 'Ma, Xueji' 'Dai, Wei' 'Sun, Aili' _publ_section_title ; A copper iodide-catalyzed coupling reaction of benzofuran-3(2H)-ones with amines: an approach to \a-ketoamides. ; _journal_issue 24 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 5294 _journal_page_last 5297 _journal_paper_doi 10.1039/d1ob00715g _journal_volume 19 _journal_year 2021 _chemical_formula_sum 'C12 H12.5 N O4' _chemical_formula_weight 234.73 _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' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-03-06 deposited with the CCDC. 2021-05-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.174(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5895(17) _cell_length_b 5.0682(7) _cell_length_c 18.033(2) _cell_measurement_reflns_used 1776 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.87 _cell_measurement_theta_min 3.24 _cell_volume 1149.8(3) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _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 'Bruker SHELXTL' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 5511 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 24.996 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 3.239 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.356 _exptl_crystal_description BLOCK _exptl_crystal_F_000 494 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.230 _refine_diff_density_max 0.242 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.028 _refine_ls_extinction_coef 0.031(4) _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 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 2009 _refine_ls_number_restraints 15 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0410 _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^)+(0.0637P)^2^+0.1028P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1156 _refine_ls_wR_factor_ref 0.1240 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1442 _reflns_number_total 2009 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00715g2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 7158100.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C12 H12.50 N O4' _cod_database_code 7158100 _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 0.977 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P2(1)/n CELL 0.71073 12.5895 5.0682 18.0329 90 92.174 90 ZERR 4 0.0017 0.0007 0.0024 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 48 50 4 16 OMIT -1 0 3 OMIT 4 0 0 OMIT -4 0 2 OMIT 0.00 50.00 L.S. 22 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 HTAB C9A O1_$3 HTAB C9A O2 HTAB C12A O3_$2 HTAB C12 O1_$3 EQIV $3 -x+1, -y+1, -z+1 HTAB C9 O3_$2 EQIV $2 -x, -y+2, -z+1 HTAB O1 O2_$1 EQIV $1 -x+1, -y+2, -z+1 HTAB O1 O2 HTAB CONF SIZE 0.26 0.25 0.23 SADI 0.04 C11 C10 C11a C10a SADI 0.04 C9 C12 C9a C12a SADI 0.04 N1 C10 N1a C10a SADI 0.04 N1 C11 N1a C11a SADI 0.04 C8 C12 C8 C12a SADI 0.04 C8 C9 C8 C9a SADI 0.04 O4 C12 O4a C12a SADI 0.04 O4 C9 O4a C9a SADI C11 C12 C11a C12a SADI C9 C10 C9a C10a SADI N1 C12 N1a C12a SADI N1 C9 N1a C9a SADI C8 N1 C8 N1a SADI O4 C10 O4a C10a SADI O4 C11 O4a C11a TEMP 23 WGHT 0.063700 0.102800 EXTI 0.030810 FVAR 0.78913 0.58718 C1 1 0.249515 0.394608 0.384424 11.00000 0.04580 0.05368 = 0.06432 0.00488 0.00203 -0.00080 AFIX 43 H1A 2 0.183820 0.397919 0.406314 11.00000 -1.20000 AFIX 0 C2 1 0.266842 0.216077 0.329671 11.00000 0.06763 0.05685 = 0.07454 -0.00946 -0.00648 -0.00144 AFIX 43 H2 2 0.213749 0.098313 0.314397 11.00000 -1.20000 AFIX 0 C3 1 0.364371 0.212726 0.297243 11.00000 0.08011 0.06872 = 0.06211 -0.01454 0.00002 0.01112 AFIX 43 H3 2 0.376397 0.091779 0.259696 11.00000 -1.20000 AFIX 0 C4 1 0.443747 0.383236 0.319070 11.00000 0.05612 0.07820 = 0.06802 -0.00771 0.01499 0.01141 AFIX 43 H4 2 0.508830 0.377093 0.296398 11.00000 -1.20000 AFIX 0 C5 1 0.427508 0.564594 0.374712 11.00000 0.04150 0.05666 = 0.06284 -0.00213 0.00492 0.00710 C6 1 0.328287 0.572867 0.408418 11.00000 0.03846 0.04510 = 0.05105 0.00326 0.00202 0.00525 C7 1 0.309027 0.757900 0.467924 11.00000 0.03648 0.05494 = 0.05785 -0.00012 0.00064 0.00524 C8 1 0.196502 0.774582 0.497342 11.00000 0.04024 0.05853 = 0.05934 0.00154 0.00625 0.00888 PART 1 C9 1 0.062410 0.627768 0.585981 21.00000 0.03443 0.06787 = 0.07025 0.00248 0.01190 0.00070 AFIX 23 H9A 2 0.023647 0.465535 0.575838 21.00000 -1.20000 H9B 2 0.021894 0.773127 0.564281 21.00000 -1.20000 AFIX 0 C10 1 0.077245 0.667340 0.668803 21.00000 0.07224 0.08956 = 0.06757 -0.00874 0.03016 0.01610 AFIX 43 H10 2 0.047608 0.805434 0.694961 21.00000 -1.20000 AFIX 0 C11 1 0.244078 0.467041 0.670929 21.00000 0.06130 0.09913 = 0.05390 0.00418 -0.00140 0.00372 AFIX 23 H11A 2 0.287569 0.330141 0.694271 21.00000 -1.20000 H11B 2 0.278032 0.635365 0.681537 21.00000 -1.20000 AFIX 0 C12 1 0.238902 0.423607 0.588819 21.00000 0.05733 0.07053 = 0.05288 -0.00064 0.00377 0.01850 AFIX 23 H12A 2 0.309415 0.440947 0.569478 21.00000 -1.20000 H12B 2 0.213425 0.246596 0.578020 21.00000 -1.20000 PART 2 AFIX 0 C9A 1 0.275817 0.601464 0.617561 -21.00000 0.04505 0.08285 = 0.05319 0.00478 -0.00142 0.00790 AFIX 23 H9AA 2 0.295102 0.722526 0.657501 -21.00000 -1.20000 H9AB 2 0.338257 0.570928 0.588846 -21.00000 -1.20000 AFIX 0 C10A 1 0.238744 0.347126 0.649058 -21.00000 0.06810 0.08797 = 0.07650 0.01250 0.00351 0.01372 AFIX 23 H10A 2 0.228175 0.219649 0.609339 -21.00000 -1.20000 H10B 2 0.292969 0.278635 0.683537 -21.00000 -1.20000 AFIX 0 C11A 1 0.061882 0.486120 0.639422 -21.00000 0.04864 0.14708 = 0.08174 0.03702 0.02007 0.00458 AFIX 23 H11C 2 -0.002584 0.508295 0.666557 -21.00000 -1.20000 H11D 2 0.046633 0.361266 0.599662 -21.00000 -1.20000 AFIX 0 C12A 1 0.090309 0.743226 0.606376 -21.00000 0.04322 0.08992 = 0.08214 0.00766 0.01261 0.00873 AFIX 23 H12C 2 0.035191 0.797390 0.570520 -21.00000 -1.20000 H12D 2 0.096295 0.876760 0.644842 -21.00000 -1.20000 PART 1 AFIX 0 N1 3 0.168136 0.614681 0.553319 21.00000 0.03977 0.05911 = 0.05093 -0.00242 0.00746 0.00968 PART 2 N1A 3 0.191243 0.717309 0.569997 -21.00000 0.03407 0.06122 = 0.05499 -0.00267 0.00608 0.00981 PART 0 O1 4 0.508384 0.727074 0.394898 11.00000 0.03955 0.08693 = 0.10786 -0.02849 0.01587 -0.00598 AFIX 147 H1 2 0.490055 0.823557 0.428602 11.00000 -1.50000 AFIX 0 O2 4 0.376407 0.912032 0.493584 11.00000 0.04741 0.08225 = 0.08417 -0.02806 0.00146 -0.00149 O3 4 0.130863 0.903286 0.461455 11.00000 0.04396 0.08522 = 0.08309 0.02337 0.00758 0.01363 PART 1 O4 4 0.142786 0.464927 0.701828 21.00000 0.06760 0.11153 = 0.05776 0.00388 0.01348 -0.00709 PART 2 O4A 4 0.140360 0.379917 0.687150 -21.00000 0.07276 0.12034 = 0.06742 0.03361 0.00426 -0.00221 PART 0 HKLF 4 REM 1_a.res in P2(1)/n REM R1 = 0.0410 for 1442 Fo > 4sig(Fo) and 0.0603 for all 2009 data REM 211 parameters refined using 15 restraints END WGHT 0.0647 0.1002 REM Instructions for potential hydrogen bonds HTAB C9 O3_$2 HTAB C12 O1_$3 HTAB C9A O1_$3 HTAB C9A O2 HTAB C12A O3_$2 HTAB O1 O2 HTAB O1 O2_$1 REM Highest difference peak 0.242, deepest hole -0.229, 1-sigma level 0.028 Q1 1 0.0049 0.6331 0.6932 11.00000 0.05 0.24 Q2 1 0.1213 0.8681 0.6747 11.00000 0.05 0.21 Q3 1 0.2479 0.7500 0.4809 11.00000 0.05 0.12 Q4 1 0.3695 0.6293 0.3794 11.00000 0.05 0.11 Q5 1 0.3838 0.3581 0.2817 11.00000 0.05 0.11 Q6 1 0.2424 0.3766 0.3317 11.00000 0.05 0.11 Q7 1 0.3608 0.7598 0.5142 11.00000 0.05 0.10 Q8 1 0.5041 0.5883 0.4367 11.00000 0.05 0.10 Q9 1 0.1651 0.9560 0.5014 11.00000 0.05 0.10 Q10 1 0.0081 0.7060 0.5409 11.00000 0.05 0.09 Q11 1 0.4256 0.7535 0.5017 11.00000 0.05 0.09 Q12 1 0.2747 0.5621 0.3829 11.00000 0.05 0.08 Q13 1 0.1550 0.7838 0.4627 11.00000 0.05 0.08 Q14 1 0.3134 0.6945 0.4193 11.00000 0.05 0.08 Q15 1 0.1901 0.3731 0.4429 11.00000 0.05 0.08 Q16 1 0.4077 0.2194 0.3364 11.00000 0.05 0.08 Q17 1 0.3053 0.2892 0.2954 11.00000 0.05 0.08 Q18 1 0.3943 0.5058 0.4136 11.00000 0.05 0.07 Q19 1 0.5648 0.5683 0.4070 11.00000 0.05 0.07 Q20 1 0.2763 0.1690 0.6809 11.00000 0.05 0.07 ; _shelx_res_checksum 3471 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.24952(13) 0.3946(3) 0.38442(10) 0.0546(5) Uani 1 1 d . . . . . H1A H 0.1838 0.3979 0.4063 0.066 Uiso 1 1 calc R U . . . C2 C 0.26684(16) 0.2161(4) 0.32967(11) 0.0666(5) Uani 1 1 d . . . . . H2 H 0.2137 0.0983 0.3144 0.080 Uiso 1 1 calc R U . . . C3 C 0.36437(16) 0.2127(4) 0.29724(11) 0.0704(6) Uani 1 1 d . . . . . H3 H 0.3764 0.0918 0.2597 0.084 Uiso 1 1 calc R U . . . C4 C 0.44375(15) 0.3832(4) 0.31907(10) 0.0671(6) Uani 1 1 d . . . . . H4 H 0.5088 0.3771 0.2964 0.081 Uiso 1 1 calc R U . . . C5 C 0.42751(12) 0.5646(3) 0.37471(10) 0.0536(5) Uani 1 1 d . . . . . C6 C 0.32829(12) 0.5729(3) 0.40842(9) 0.0449(4) Uani 1 1 d . . . . . C7 C 0.30903(12) 0.7579(3) 0.46792(9) 0.0498(4) Uani 1 1 d . . . . . C8 C 0.19650(12) 0.7746(3) 0.49734(9) 0.0526(5) Uani 1 1 d D . . . . C9 C 0.0624(3) 0.6278(10) 0.5860(3) 0.0573(11) Uani 0.587(5) 1 d D . P A 1 H9A H 0.0236 0.4655 0.5758 0.069 Uiso 0.587(5) 1 calc R U P A 1 H9B H 0.0219 0.7731 0.5643 0.069 Uiso 0.587(5) 1 calc R U P A 1 C10 C 0.0772(3) 0.6673(11) 0.6688(2) 0.0758(13) Uani 0.587(5) 1 d D . P A 1 H10 H 0.0476 0.8054 0.6950 0.091 Uiso 0.587(5) 1 calc R U P A 1 C11 C 0.2441(5) 0.4670(14) 0.6709(3) 0.0715(16) Uani 0.587(5) 1 d D . P A 1 H11A H 0.2876 0.3301 0.6943 0.086 Uiso 0.587(5) 1 calc R U P A 1 H11B H 0.2780 0.6354 0.6815 0.086 Uiso 0.587(5) 1 calc R U P A 1 C12 C 0.2389(3) 0.4236(8) 0.58882(19) 0.0602(11) Uani 0.587(5) 1 d D . P A 1 H12A H 0.3094 0.4409 0.5695 0.072 Uiso 0.587(5) 1 calc R U P A 1 H12B H 0.2134 0.2466 0.5780 0.072 Uiso 0.587(5) 1 calc R U P A 1 C9A C 0.2758(3) 0.6015(11) 0.6176(3) 0.0605(16) Uani 0.413(5) 1 d D . P A 2 H9AA H 0.2951 0.7225 0.6575 0.073 Uiso 0.413(5) 1 calc R U P A 2 H9AB H 0.3383 0.5709 0.5888 0.073 Uiso 0.413(5) 1 calc R U P A 2 C10A C 0.2387(7) 0.3471(16) 0.6491(5) 0.078(2) Uani 0.413(5) 1 d D . P A 2 H10A H 0.2282 0.2196 0.6093 0.093 Uiso 0.413(5) 1 calc R U P A 2 H10B H 0.2930 0.2786 0.6835 0.093 Uiso 0.413(5) 1 calc R U P A 2 C11A C 0.0619(4) 0.4861(18) 0.6394(4) 0.092(2) Uani 0.413(5) 1 d D . P A 2 H11C H -0.0026 0.5083 0.6666 0.110 Uiso 0.413(5) 1 calc R U P A 2 H11D H 0.0466 0.3613 0.5997 0.110 Uiso 0.413(5) 1 calc R U P A 2 C12A C 0.0903(5) 0.7432(15) 0.6064(5) 0.0715(19) Uani 0.413(5) 1 d D . P A 2 H12C H 0.0352 0.7974 0.5705 0.086 Uiso 0.413(5) 1 calc R U P A 2 H12D H 0.0963 0.8768 0.6448 0.086 Uiso 0.413(5) 1 calc R U P A 2 N1 N 0.1681(3) 0.6147(8) 0.5533(2) 0.0498(9) Uani 0.587(5) 1 d D . P A 1 N1A N 0.1912(4) 0.7173(12) 0.5700(3) 0.0500(13) Uani 0.413(5) 1 d D . P A 2 O1 O 0.50838(9) 0.7271(3) 0.39490(8) 0.0778(5) Uani 1 1 d . . . . . H1 H 0.4901 0.8236 0.4286 0.117 Uiso 1 1 calc R U . . . O2 O 0.37641(9) 0.9120(3) 0.49358(7) 0.0713(4) Uani 1 1 d . . . . . O3 O 0.13086(9) 0.9033(3) 0.46146(7) 0.0706(4) Uani 1 1 d . . . . . O4 O 0.1428(10) 0.4649(18) 0.7018(4) 0.0787(19) Uani 0.587(5) 1 d D . P A 1 O4A O 0.1404(14) 0.380(2) 0.6871(6) 0.087(3) Uani 0.413(5) 1 d D . 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 C1 0.0458(9) 0.0537(10) 0.0643(11) 0.0049(9) 0.0020(8) -0.0008(8) C2 0.0676(12) 0.0569(11) 0.0745(12) -0.0095(10) -0.0065(9) -0.0014(10) C3 0.0801(13) 0.0687(13) 0.0621(11) -0.0145(10) 0.0000(10) 0.0111(11) C4 0.0561(11) 0.0782(13) 0.0680(12) -0.0077(10) 0.0150(9) 0.0114(10) C5 0.0415(9) 0.0567(10) 0.0628(11) -0.0021(8) 0.0049(8) 0.0071(8) C6 0.0385(8) 0.0451(9) 0.0511(9) 0.0033(7) 0.0020(7) 0.0053(7) C7 0.0365(8) 0.0549(10) 0.0579(10) -0.0001(8) 0.0006(7) 0.0052(7) C8 0.0402(9) 0.0585(10) 0.0593(11) 0.0015(9) 0.0063(8) 0.0089(8) C9 0.034(2) 0.068(3) 0.070(3) 0.002(2) 0.0119(17) 0.0007(17) C10 0.072(2) 0.090(3) 0.068(3) -0.009(2) 0.030(2) 0.016(2) C11 0.061(2) 0.099(4) 0.054(3) 0.004(3) -0.001(2) 0.004(3) C12 0.0573(19) 0.071(2) 0.053(2) -0.0006(18) 0.0038(15) 0.0185(17) C9A 0.045(2) 0.083(4) 0.053(3) 0.005(3) -0.001(2) 0.008(2) C10A 0.068(4) 0.088(6) 0.076(6) 0.012(4) 0.004(4) 0.014(4) C11A 0.049(3) 0.147(7) 0.082(5) 0.037(5) 0.020(3) 0.005(4) C12A 0.043(3) 0.090(6) 0.082(5) 0.008(4) 0.013(3) 0.009(3) N1 0.0398(19) 0.059(2) 0.051(2) -0.0024(16) 0.0075(14) 0.0097(16) N1A 0.034(3) 0.061(4) 0.055(3) -0.003(2) 0.0061(19) 0.010(2) O1 0.0396(7) 0.0869(10) 0.1079(11) -0.0285(8) 0.0159(6) -0.0060(7) O2 0.0474(7) 0.0823(9) 0.0842(9) -0.0281(7) 0.0015(6) -0.0015(7) O3 0.0440(7) 0.0852(10) 0.0831(9) 0.0234(7) 0.0076(6) 0.0136(6) O4 0.068(2) 0.112(5) 0.058(2) 0.004(2) 0.013(2) -0.007(3) O4A 0.073(4) 0.120(8) 0.067(5) 0.034(5) 0.004(4) -0.002(6) 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' 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 C2 C1 C6 121.47(17) . . ? C2 C1 H1A 119.3 . . ? C6 C1 H1A 119.3 . . ? C1 C2 C3 118.99(18) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.49(18) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 120.18(17) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? O1 C5 C4 118.11(15) . . ? O1 C5 C6 122.51(15) . . ? C4 C5 C6 119.38(16) . . ? C1 C6 C5 118.48(15) . . ? C1 C6 C7 120.64(14) . . ? C5 C6 C7 120.86(14) . . ? O2 C7 C6 123.76(14) . . ? O2 C7 C8 117.87(15) . . ? C6 C7 C8 118.26(14) . . ? O3 C8 N1A 125.1(3) . . ? O3 C8 N1 121.6(2) . . ? O3 C8 C7 117.53(15) . . ? N1A C8 C7 113.9(3) . . ? N1 C8 C7 119.9(2) . . ? N1 C9 C10 108.7(3) . . ? N1 C9 H9A 110.0 . . ? C10 C9 H9A 110.0 . . ? N1 C9 H9B 110.0 . . ? C10 C9 H9B 110.0 . . ? H9A C9 H9B 108.3 . . ? O4 C10 C9 111.3(4) . . ? O4 C10 H10 124.3 . . ? C9 C10 H10 124.3 . . ? O4 C11 C12 112.6(6) . . ? O4 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? O4 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? N1 C12 C11 110.0(3) . . ? N1 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N1 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N1A C9A C10A 109.8(5) . . ? N1A C9A H9AA 109.7 . . ? C10A C9A H9AA 109.7 . . ? N1A C9A H9AB 109.7 . . ? C10A C9A H9AB 109.7 . . ? H9AA C9A H9AB 108.2 . . ? O4A C10A C9A 111.5(7) . . ? O4A C10A H10A 109.3 . . ? C9A C10A H10A 109.3 . . ? O4A C10A H10B 109.3 . . ? C9A C10A H10B 109.3 . . ? H10A C10A H10B 108.0 . . ? O4A C11A C12A 114.3(8) . . ? O4A C11A H11C 108.7 . . ? C12A C11A H11C 108.7 . . ? O4A C11A H11D 108.7 . . ? C12A C11A H11D 108.7 . . ? H11C C11A H11D 107.6 . . ? N1A C12A C11A 109.2(6) . . ? N1A C12A H12C 109.8 . . ? C11A C12A H12C 109.8 . . ? N1A C12A H12D 109.8 . . ? C11A C12A H12D 109.8 . . ? H12C C12A H12D 108.3 . . ? C8 N1 C12 123.7(3) . . ? C8 N1 C9 122.5(4) . . ? C12 N1 C9 113.7(4) . . ? C8 N1A C12A 119.6(5) . . ? C8 N1A C9A 126.5(5) . . ? C12A N1A C9A 113.5(5) . . ? C5 O1 H1 109.5 . . ? C11 O4 C10 110.2(6) . . ? C11A O4A C10A 110.5(8) . . ? 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 C2 1.363(2) . ? C1 C6 1.398(2) . ? C1 H1A 0.9300 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.368(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(2) . ? C4 H4 0.9300 . ? C5 O1 1.349(2) . ? C5 C6 1.410(2) . ? C6 C7 1.452(2) . ? C7 O2 1.2305(19) . ? C7 C8 1.534(2) . ? C8 O3 1.2193(19) . ? C8 N1A 1.346(6) . ? C8 N1 1.353(4) . ? C9 N1 1.477(6) . ? C9 C10 1.511(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O4 1.432(12) . ? C10 H10 0.9300 . ? C11 O4 1.411(13) . ? C11 C12 1.496(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.448(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C9A N1A 1.465(7) . ? C9A C10A 1.491(10) . ? C9A H9AA 0.9700 . ? C9A H9AB 0.9700 . ? C10A O4A 1.449(17) . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C11A O4A 1.394(17) . ? C11A C12A 1.482(10) . ? C11A H11C 0.9700 . ? C11A H11D 0.9700 . ? C12A N1A 1.458(8) . ? C12A H12C 0.9700 . ? C12A H12D 0.9700 . ? O1 H1 0.8200 . ? 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 C9A H9AB O1 0.97 2.46 3.202(4) 133.0 3_666 C9A H9AB O2 0.97 2.50 3.049(5) 116.0 . C12A H12C O3 0.97 2.63 3.493(7) 148.5 3_576 C12 H12A O1 0.97 2.51 3.274(3) 135.9 3_666 C9 H9B O3 0.97 2.56 3.485(5) 160.2 3_576 O1 H1 O2 0.82 2.53 3.0450(19) 121.8 3_676 O1 H1 O2 0.82 1.94 2.6515(17) 145.3 . 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 C6 C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 O1 179.38(17) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? C2 C1 C6 C7 -178.70(16) . . . . ? O1 C5 C6 C1 -179.27(15) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? O1 C5 C6 C7 -0.7(3) . . . . ? C4 C5 C6 C7 178.95(16) . . . . ? C1 C6 C7 O2 176.90(16) . . . . ? C5 C6 C7 O2 -1.6(3) . . . . ? C1 C6 C7 C8 -7.0(2) . . . . ? C5 C6 C7 C8 174.48(15) . . . . ? O2 C7 C8 O3 96.4(2) . . . . ? C6 C7 C8 O3 -79.9(2) . . . . ? O2 C7 C8 N1A -63.6(3) . . . . ? C6 C7 C8 N1A 120.1(3) . . . . ? O2 C7 C8 N1 -94.8(3) . . . . ? C6 C7 C8 N1 88.9(3) . . . . ? N1 C9 C10 O4 -55.8(7) . . . . ? O4 C11 C12 N1 54.7(7) . . . . ? N1A C9A C10A O4A -54.5(10) . . . . ? O4A C11A C12A N1A 54.3(11) . . . . ? O3 C8 N1 C12 168.6(3) . . . . ? C7 C8 N1 C12 0.3(4) . . . . ? O3 C8 N1 C9 -14.0(4) . . . . ? C7 C8 N1 C9 177.7(3) . . . . ? C11 C12 N1 C8 125.8(5) . . . . ? C11 C12 N1 C9 -51.7(5) . . . . ? C10 C9 N1 C8 -125.1(5) . . . . ? C10 C9 N1 C12 52.5(5) . . . . ? O3 C8 N1A C12A 17.6(6) . . . . ? C7 C8 N1A C12A 175.8(4) . . . . ? O3 C8 N1A C9A -169.4(4) . . . . ? C7 C8 N1A C9A -11.1(6) . . . . ? C11A C12A N1A C8 122.4(8) . . . . ? C11A C12A N1A C9A -51.6(8) . . . . ? C10A C9A N1A C8 -120.5(7) . . . . ? C10A C9A N1A C12A 53.0(7) . . . . ? C12 C11 O4 C10 -59.4(8) . . . . ? C9 C10 O4 C11 60.1(7) . . . . ? C12A C11A O4A C10A -57.6(12) . . . . ? C9A C10A O4A C11A 57.1(12) . . . . ?