#------------------------------------------------------------------------------ #$Date: 2020-04-09 06:48:44 +0300 (Thu, 09 Apr 2020) $ #$Revision: 250531 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157461.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_7157461 loop_ _publ_author_name 'Kaliyamoorthy, Alagiri' 'Rayaroth, Amritha' 'Singh, Rajat Kumar' 'A. V. , Kalyanakrishnan' 'Hari, Krishna' _publ_section_title ; Base-promoted 1,6-Conjugate Addition of Alkylazaarenes to para-Quinone Methides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00419G _journal_year 2020 _chemical_formula_moiety 'C27 H33 N O ' _chemical_formula_sum 'C27 H33 N O' _chemical_formula_weight 387.54 _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_block_doi 10.5517/ccdc.csd.cc24ffbc _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-21 deposited with the CCDC. 2020-04-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.967(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.3170(9) _cell_length_b 18.704(2) _cell_length_c 13.6865(14) _cell_measurement_reflns_used 6384 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.02 _cell_measurement_theta_min 2.18 _cell_volume 2379.4(4) _computing_cell_refinement 'APEX3/SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2016)' _computing_molecular_graphics 'ORTEP3- 2014.1(Farrugia, 1997) ' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker KAPPA 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 0.0426 _diffrn_reflns_av_unetI/netI 0.0289 _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 -10 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 32653 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.178 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2016)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_meas 1.081 _exptl_crystal_density_method NONE _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.212 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 4184 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0569 _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^)+(0.0570P)^2^+1.2432P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1319 _refine_ls_wR_factor_ref 0.1646 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2711 _reflns_number_total 4184 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00419g2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7157461 _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_min 0.988 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL shelxt_a.res in P2(1)/n shelx.res created by SHELXL-2018/3 at 15:05:49 on 08-Jan-2020 CELL 0.71073 9.3170 18.7039 13.6865 90.000 93.967 90.000 ZERR 4.00 0.0009 0.0020 0.0014 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 108 132 4 4 MERG 2 OMIT -3.00 50.00 OMIT 0 1 1 EQIV $1 x-1/2, -y+1/2, z-1/2 HTAB O1 N1_$1 FMAP 2 PLAN 5 SIZE 0.110 0.140 0.180 ACTA HTAB 2.00000 BOND CONF L.S. 10 TEMP 23.00 WGHT 0.057000 1.243200 FVAR 0.15064 C1 1 0.427508 0.327960 0.278189 11.00000 0.04894 0.04506 = 0.04561 -0.00063 -0.00415 -0.00213 C2 1 0.387728 0.365107 0.193451 11.00000 0.05612 0.03990 = 0.04796 -0.00036 -0.00255 -0.00656 AFIX 43 H2 2 0.425698 0.410512 0.185133 11.00000 -1.20000 AFIX 0 C3 1 0.293033 0.337299 0.119954 11.00000 0.04379 0.05044 = 0.04076 -0.00410 0.00180 -0.00023 C4 1 0.236391 0.269131 0.136137 11.00000 0.04137 0.05888 = 0.04319 -0.00754 0.00267 -0.01235 C5 1 0.279210 0.228574 0.218731 11.00000 0.04731 0.04881 = 0.05442 -0.00279 0.00350 -0.00997 C6 1 0.374172 0.260042 0.288443 11.00000 0.05295 0.04618 = 0.04996 0.00324 -0.00541 -0.00707 AFIX 43 H6 2 0.402954 0.234147 0.344415 11.00000 -1.20000 AFIX 0 C7 1 0.254277 0.379438 0.025460 11.00000 0.06366 0.06141 = 0.04418 0.00049 -0.00409 -0.00412 C8 1 0.097199 0.402320 0.021259 11.00000 0.09229 0.16754 = 0.07930 0.02924 -0.00253 0.05439 AFIX 137 H8A 2 0.075042 0.429885 -0.037007 11.00000 -1.50000 H8B 2 0.080641 0.430812 0.077728 11.00000 -1.50000 H8C 2 0.036841 0.360695 0.020408 11.00000 -1.50000 AFIX 0 C9 1 0.281183 0.335609 -0.065231 11.00000 0.11569 0.09100 = 0.04970 0.00370 0.01875 -0.00590 AFIX 137 H9A 2 0.217712 0.295122 -0.069034 11.00000 -1.50000 H9B 2 0.379161 0.319374 -0.061231 11.00000 -1.50000 H9C 2 0.263640 0.364699 -0.122605 11.00000 -1.50000 AFIX 0 C10 1 0.346854 0.446304 0.019195 11.00000 0.16187 0.07597 = 0.07548 0.03039 -0.03728 -0.03409 AFIX 137 H10A 2 0.446657 0.433098 0.024541 11.00000 -1.50000 H10B 2 0.327610 0.478280 0.071576 11.00000 -1.50000 H10C 2 0.324573 0.469626 -0.042477 11.00000 -1.50000 AFIX 0 C11 1 0.225871 0.151934 0.234793 11.00000 0.08374 0.05862 = 0.07669 0.00530 -0.00762 -0.02906 C12 1 0.254905 0.104385 0.146420 11.00000 0.16920 0.05769 = 0.14609 -0.02567 0.01774 -0.03733 AFIX 137 H12A 2 0.355804 0.105086 0.136214 11.00000 -1.50000 H12B 2 0.201516 0.122184 0.089007 11.00000 -1.50000 H12C 2 0.225490 0.056251 0.158956 11.00000 -1.50000 AFIX 0 C13 1 0.065904 0.153009 0.252359 11.00000 0.09823 0.12937 = 0.10503 0.02391 0.01203 -0.05699 AFIX 137 H13A 2 0.035912 0.106007 0.270420 11.00000 -1.50000 H13B 2 0.011823 0.167730 0.193542 11.00000 -1.50000 H13C 2 0.049353 0.185966 0.304163 11.00000 -1.50000 AFIX 0 C14 1 0.305252 0.117364 0.323826 11.00000 0.16925 0.06898 = 0.14665 0.04589 -0.05409 -0.05088 AFIX 137 H14A 2 0.407007 0.123712 0.320289 11.00000 -1.50000 H14B 2 0.283327 0.067229 0.324796 11.00000 -1.50000 H14C 2 0.275396 0.139388 0.382445 11.00000 -1.50000 AFIX 0 C15 1 0.522318 0.360989 0.361753 11.00000 0.05589 0.04485 = 0.04573 0.00425 -0.00908 -0.00797 AFIX 13 H15 2 0.560577 0.321109 0.402047 11.00000 -1.20000 AFIX 0 C16 1 0.650793 0.400010 0.326400 11.00000 0.06239 0.05384 = 0.04039 0.00131 -0.01181 -0.01496 C17 1 0.759309 0.360485 0.288997 11.00000 0.08122 0.06668 = 0.07596 -0.00492 0.01263 -0.01654 AFIX 43 H17 2 0.750990 0.310957 0.286628 11.00000 -1.20000 AFIX 0 C18 1 0.879553 0.392201 0.255076 11.00000 0.08410 0.10898 = 0.09648 -0.00888 0.02522 -0.02407 AFIX 43 H18 2 0.951260 0.364367 0.230187 11.00000 -1.20000 AFIX 0 C19 1 0.892686 0.465204 0.258305 11.00000 0.09600 0.11278 = 0.08153 0.00310 0.01066 -0.05395 AFIX 43 H19 2 0.972529 0.487210 0.234266 11.00000 -1.20000 AFIX 0 C20 1 0.789396 0.505089 0.296479 11.00000 0.12061 0.07035 = 0.10338 0.00328 0.01068 -0.04026 AFIX 43 H20 2 0.799759 0.554483 0.300326 11.00000 -1.20000 AFIX 0 C21 1 0.668285 0.472961 0.329895 11.00000 0.08727 0.05809 = 0.08712 0.00150 0.00453 -0.01829 AFIX 43 H21 2 0.597515 0.501208 0.355150 11.00000 -1.20000 AFIX 0 C22 1 0.431941 0.406267 0.427686 11.00000 0.07035 0.06442 = 0.05361 -0.00616 -0.00525 -0.00676 AFIX 23 H22A 2 0.494860 0.427432 0.479235 11.00000 -1.20000 H22B 2 0.387312 0.444889 0.389273 11.00000 -1.20000 AFIX 0 C23 1 0.317186 0.364212 0.473177 11.00000 0.05640 0.08138 = 0.05219 -0.00995 -0.00353 -0.00734 C24 1 0.173804 0.375535 0.449740 11.00000 0.06264 0.11999 = 0.09324 -0.00231 -0.00940 0.00995 AFIX 43 H24 2 0.144617 0.410969 0.405013 11.00000 -1.20000 AFIX 0 C25 1 0.073294 0.334571 0.492287 11.00000 0.04739 0.19113 = 0.11856 -0.01459 0.00127 -0.00984 AFIX 43 H25 2 -0.024259 0.341393 0.475805 11.00000 -1.20000 AFIX 0 C26 1 0.116882 0.284797 0.557610 11.00000 0.06855 0.17828 = 0.10396 0.00555 0.01672 -0.03742 AFIX 43 H26 2 0.050718 0.257381 0.589056 11.00000 -1.20000 AFIX 0 C27 1 0.259450 0.275369 0.576738 11.00000 0.07194 0.15758 = 0.10885 0.04553 0.01462 -0.02204 AFIX 43 H27 2 0.289460 0.239478 0.620533 11.00000 -1.20000 AFIX 0 N1 3 0.360356 0.314251 0.536847 11.00000 0.05496 0.12363 = 0.07683 0.03037 0.00302 -0.01040 O1 4 0.142851 0.242882 0.063273 11.00000 0.09162 0.12853 = 0.05314 0.00416 -0.01370 -0.06618 AFIX 147 H1 2 0.071782 0.226381 0.087342 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/n REM wR2 = 0.1646, GooF = S = 1.038, Restrained GooF = 1.038 for all data REM R1 = 0.0569 for 2711 Fo > 4sig(Fo) and 0.0955 for all 4184 data REM 269 parameters refined using 0 restraints END WGHT 0.0559 1.2404 REM Instructions for potential hydrogen bonds HTAB O1 N1_$1 REM Highest difference peak 0.212, deepest hole -0.184, 1-sigma level 0.036 Q1 1 0.2300 0.1467 0.3848 11.00000 0.05 0.21 Q2 1 0.3844 0.4841 0.0687 11.00000 0.05 0.16 Q3 1 0.0005 0.1946 0.2366 11.00000 0.05 0.16 Q4 1 0.2569 0.4867 -0.0219 11.00000 0.05 0.15 Q5 1 0.3215 0.2861 -0.0620 11.00000 0.05 0.15 ; _shelx_res_checksum 51883 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 0.4275(2) 0.32796(12) 0.27819(16) 0.0469(5) Uani 1 1 d . . . . . C2 C 0.3877(2) 0.36511(12) 0.19345(15) 0.0483(6) Uani 1 1 d . . . . . H2 H 0.425698 0.410512 0.185133 0.058 Uiso 1 1 calc R U . . . C3 C 0.2930(2) 0.33730(12) 0.11995(15) 0.0450(5) Uani 1 1 d . . . . . C4 C 0.2364(2) 0.26913(12) 0.13614(15) 0.0478(6) Uani 1 1 d . . . . . C5 C 0.2792(2) 0.22857(12) 0.21873(17) 0.0502(6) Uani 1 1 d . . . . . C6 C 0.3742(2) 0.26004(12) 0.28844(16) 0.0501(6) Uani 1 1 d . . . . . H6 H 0.402954 0.234147 0.344415 0.060 Uiso 1 1 calc R U . . . C7 C 0.2543(3) 0.37944(13) 0.02546(16) 0.0568(6) Uani 1 1 d . . . . . C8 C 0.0972(4) 0.4023(2) 0.0213(2) 0.1134(14) Uani 1 1 d . . . . . H8A H 0.075042 0.429885 -0.037007 0.170 Uiso 1 1 calc R U . . . H8B H 0.080641 0.430812 0.077728 0.170 Uiso 1 1 calc R U . . . H8C H 0.036841 0.360695 0.020408 0.170 Uiso 1 1 calc R U . . . C9 C 0.2812(4) 0.33561(17) -0.06523(19) 0.0849(9) Uani 1 1 d . . . . . H9A H 0.217712 0.295122 -0.069034 0.127 Uiso 1 1 calc R U . . . H9B H 0.379161 0.319374 -0.061231 0.127 Uiso 1 1 calc R U . . . H9C H 0.263640 0.364699 -0.122605 0.127 Uiso 1 1 calc R U . . . C10 C 0.3469(4) 0.44630(17) 0.0192(2) 0.1065(13) Uani 1 1 d . . . . . H10A H 0.446657 0.433098 0.024541 0.160 Uiso 1 1 calc R U . . . H10B H 0.327610 0.478280 0.071576 0.160 Uiso 1 1 calc R U . . . H10C H 0.324573 0.469626 -0.042477 0.160 Uiso 1 1 calc R U . . . C11 C 0.2259(3) 0.15193(15) 0.2348(2) 0.0736(8) Uani 1 1 d . . . . . C12 C 0.2549(5) 0.10439(18) 0.1464(3) 0.1240(15) Uani 1 1 d . . . . . H12A H 0.355804 0.105086 0.136214 0.186 Uiso 1 1 calc R U . . . H12B H 0.201516 0.122184 0.089007 0.186 Uiso 1 1 calc R U . . . H12C H 0.225490 0.056251 0.158956 0.186 Uiso 1 1 calc R U . . . C13 C 0.0659(4) 0.1530(2) 0.2524(3) 0.1106(13) Uani 1 1 d . . . . . H13A H 0.035912 0.106007 0.270420 0.166 Uiso 1 1 calc R U . . . H13B H 0.011823 0.167730 0.193542 0.166 Uiso 1 1 calc R U . . . H13C H 0.049353 0.185966 0.304163 0.166 Uiso 1 1 calc R U . . . C14 C 0.3053(5) 0.11736(18) 0.3238(3) 0.1313(17) Uani 1 1 d . . . . . H14A H 0.407007 0.123712 0.320289 0.197 Uiso 1 1 calc R U . . . H14B H 0.283327 0.067229 0.324796 0.197 Uiso 1 1 calc R U . . . H14C H 0.275396 0.139388 0.382445 0.197 Uiso 1 1 calc R U . . . C15 C 0.5223(2) 0.36099(12) 0.36175(16) 0.0494(6) Uani 1 1 d . . . . . H15 H 0.560577 0.321109 0.402047 0.059 Uiso 1 1 calc R U . . . C16 C 0.6508(3) 0.40001(13) 0.32640(16) 0.0529(6) Uani 1 1 d . . . . . C17 C 0.7593(3) 0.36049(16) 0.2890(2) 0.0743(8) Uani 1 1 d . . . . . H17 H 0.750990 0.310957 0.286628 0.089 Uiso 1 1 calc R U . . . C18 C 0.8796(4) 0.3922(2) 0.2551(2) 0.0956(10) Uani 1 1 d . . . . . H18 H 0.951260 0.364367 0.230187 0.115 Uiso 1 1 calc R U . . . C19 C 0.8927(4) 0.4652(2) 0.2583(2) 0.0966(11) Uani 1 1 d . . . . . H19 H 0.972529 0.487210 0.234266 0.116 Uiso 1 1 calc R U . . . C20 C 0.7894(4) 0.50509(19) 0.2965(3) 0.0980(11) Uani 1 1 d . . . . . H20 H 0.799759 0.554483 0.300326 0.118 Uiso 1 1 calc R U . . . C21 C 0.6683(3) 0.47296(15) 0.3299(2) 0.0776(8) Uani 1 1 d . . . . . H21 H 0.597515 0.501208 0.355150 0.093 Uiso 1 1 calc R U . . . C22 C 0.4319(3) 0.40627(14) 0.42769(18) 0.0632(7) Uani 1 1 d . . . . . H22A H 0.494860 0.427432 0.479235 0.076 Uiso 1 1 calc R U . . . H22B H 0.387312 0.444889 0.389273 0.076 Uiso 1 1 calc R U . . . C23 C 0.3172(3) 0.36421(15) 0.47318(18) 0.0637(7) Uani 1 1 d . . . . . C24 C 0.1738(3) 0.3755(2) 0.4497(2) 0.0926(10) Uani 1 1 d . . . . . H24 H 0.144617 0.410969 0.405013 0.111 Uiso 1 1 calc R U . . . C25 C 0.0733(4) 0.3346(3) 0.4923(3) 0.1192(15) Uani 1 1 d . . . . . H25 H -0.024259 0.341393 0.475805 0.143 Uiso 1 1 calc R U . . . C26 C 0.1169(4) 0.2848(3) 0.5576(3) 0.1164(14) Uani 1 1 d . . . . . H26 H 0.050718 0.257381 0.589056 0.140 Uiso 1 1 calc R U . . . C27 C 0.2595(4) 0.2754(2) 0.5767(3) 0.1124(13) Uani 1 1 d . . . . . H27 H 0.289460 0.239478 0.620533 0.135 Uiso 1 1 calc R U . . . N1 N 0.3604(2) 0.31425(15) 0.53685(18) 0.0852(8) Uani 1 1 d . . . . . O1 O 0.1429(2) 0.24288(13) 0.06327(12) 0.0920(7) Uani 1 1 d . . . . . H1 H 0.071782 0.226381 0.087342 0.138 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 C1 0.0489(12) 0.0451(13) 0.0456(12) -0.0006(10) -0.0042(10) -0.0021(10) C2 0.0561(14) 0.0399(12) 0.0480(13) -0.0004(10) -0.0026(11) -0.0066(10) C3 0.0438(12) 0.0504(13) 0.0408(12) -0.0041(10) 0.0018(9) -0.0002(10) C4 0.0414(12) 0.0589(15) 0.0432(12) -0.0075(11) 0.0027(10) -0.0124(11) C5 0.0473(13) 0.0488(14) 0.0544(14) -0.0028(11) 0.0035(11) -0.0100(11) C6 0.0530(13) 0.0462(13) 0.0500(13) 0.0032(10) -0.0054(11) -0.0071(11) C7 0.0637(15) 0.0614(16) 0.0442(13) 0.0005(11) -0.0041(11) -0.0041(12) C8 0.092(2) 0.168(4) 0.079(2) 0.029(2) -0.0025(18) 0.054(2) C9 0.116(3) 0.091(2) 0.0497(15) 0.0037(15) 0.0188(16) -0.0059(19) C10 0.162(3) 0.076(2) 0.075(2) 0.0304(17) -0.037(2) -0.034(2) C11 0.0837(19) 0.0586(17) 0.0767(18) 0.0053(14) -0.0076(15) -0.0291(15) C12 0.169(4) 0.058(2) 0.146(3) -0.026(2) 0.018(3) -0.037(2) C13 0.098(3) 0.129(3) 0.105(3) 0.024(2) 0.012(2) -0.057(2) C14 0.169(4) 0.069(2) 0.147(3) 0.046(2) -0.054(3) -0.051(2) C15 0.0559(13) 0.0449(13) 0.0457(12) 0.0042(10) -0.0091(10) -0.0080(11) C16 0.0624(15) 0.0538(14) 0.0404(12) 0.0013(11) -0.0118(11) -0.0150(12) C17 0.0812(19) 0.0667(18) 0.0760(19) -0.0049(15) 0.0126(16) -0.0165(16) C18 0.084(2) 0.109(3) 0.096(2) -0.009(2) 0.0252(18) -0.024(2) C19 0.096(3) 0.113(3) 0.082(2) 0.003(2) 0.0107(19) -0.054(2) C20 0.121(3) 0.070(2) 0.103(3) 0.0033(19) 0.011(2) -0.040(2) C21 0.087(2) 0.0581(17) 0.087(2) 0.0015(15) 0.0045(16) -0.0183(15) C22 0.0704(17) 0.0644(16) 0.0536(15) -0.0062(12) -0.0052(13) -0.0068(13) C23 0.0564(15) 0.0814(19) 0.0522(15) -0.0099(14) -0.0035(12) -0.0073(14) C24 0.0626(19) 0.120(3) 0.093(2) -0.002(2) -0.0094(17) 0.0100(18) C25 0.0474(18) 0.191(5) 0.119(3) -0.015(3) 0.001(2) -0.010(2) C26 0.069(2) 0.178(4) 0.104(3) 0.006(3) 0.017(2) -0.037(3) C27 0.072(2) 0.158(4) 0.109(3) 0.046(3) 0.0146(19) -0.022(2) N1 0.0550(14) 0.124(2) 0.0768(16) 0.0304(16) 0.0030(12) -0.0104(14) O1 0.0916(15) 0.1285(18) 0.0531(10) 0.0042(11) -0.0137(10) -0.0662(14) 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 C6 C1 C2 118.2(2) . . ? C6 C1 C15 119.47(19) . . ? C2 C1 C15 122.25(19) . . ? C1 C2 C3 122.6(2) . . ? C2 C3 C4 116.9(2) . . ? C2 C3 C7 121.1(2) . . ? C4 C3 C7 122.00(19) . . ? O1 C4 C5 121.8(2) . . ? O1 C4 C3 116.0(2) . . ? C5 C4 C3 122.13(19) . . ? C6 C5 C4 117.3(2) . . ? C6 C5 C11 119.6(2) . . ? C4 C5 C11 123.0(2) . . ? C1 C6 C5 122.7(2) . . ? C8 C7 C9 109.4(2) . . ? C8 C7 C10 108.3(3) . . ? C9 C7 C10 105.7(2) . . ? C8 C7 C3 110.2(2) . . ? C9 C7 C3 111.6(2) . . ? C10 C7 C3 111.5(2) . . ? C14 C11 C13 107.7(3) . . ? C14 C11 C5 111.5(2) . . ? C13 C11 C5 109.8(3) . . ? C14 C11 C12 106.3(3) . . ? C13 C11 C12 111.0(3) . . ? C5 C11 C12 110.5(2) . . ? C16 C15 C1 112.71(18) . . ? C16 C15 C22 113.70(19) . . ? C1 C15 C22 110.61(19) . . ? C21 C16 C17 117.2(2) . . ? C21 C16 C15 124.3(2) . . ? C17 C16 C15 118.5(2) . . ? C18 C17 C16 121.9(3) . . ? C19 C18 C17 119.4(3) . . ? C20 C19 C18 119.9(3) . . ? C19 C20 C21 120.5(3) . . ? C16 C21 C20 121.1(3) . . ? C23 C22 C15 113.1(2) . . ? N1 C23 C24 120.8(3) . . ? N1 C23 C22 116.9(2) . . ? C24 C23 C22 122.3(3) . . ? C23 C24 C25 119.9(3) . . ? C26 C25 C24 119.3(3) . . ? C25 C26 C27 118.1(4) . . ? N1 C27 C26 124.2(4) . . ? C23 N1 C27 117.7(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 C1 C6 1.375(3) . ? C1 C2 1.380(3) . ? C1 C15 1.527(3) . ? C2 C3 1.392(3) . ? C3 C4 1.403(3) . ? C3 C7 1.536(3) . ? C4 O1 1.369(3) . ? C4 C5 1.396(3) . ? C5 C6 1.387(3) . ? C5 C11 1.538(3) . ? C7 C8 1.522(4) . ? C7 C9 1.523(4) . ? C7 C10 1.525(4) . ? C11 C14 1.525(4) . ? C11 C13 1.526(4) . ? C11 C12 1.540(5) . ? C15 C16 1.510(3) . ? C15 C22 1.532(3) . ? C16 C21 1.375(4) . ? C16 C17 1.379(4) . ? C17 C18 1.376(4) . ? C18 C19 1.371(5) . ? C19 C20 1.351(5) . ? C20 C21 1.384(4) . ? C22 C23 1.497(4) . ? C23 N1 1.321(3) . ? C23 C24 1.369(4) . ? C24 C25 1.371(5) . ? C25 C26 1.334(6) . ? C26 C27 1.348(5) . ? C27 N1 1.335(4) . ? 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 _geom_hbond_publ_flag O1 H1 N1 0.82 2.18 2.841(3) 137.8 4_565 yes 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 1.9(3) . . . . ? C15 C1 C2 C3 -175.3(2) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C1 C2 C3 C7 -178.4(2) . . . . ? C2 C3 C4 O1 179.6(2) . . . . ? C7 C3 C4 O1 -0.9(3) . . . . ? C2 C3 C4 C5 -4.1(3) . . . . ? C7 C3 C4 C5 175.3(2) . . . . ? O1 C4 C5 C6 -179.9(2) . . . . ? C3 C4 C5 C6 4.0(3) . . . . ? O1 C4 C5 C11 0.0(4) . . . . ? C3 C4 C5 C11 -176.0(2) . . . . ? C2 C1 C6 C5 -2.0(3) . . . . ? C15 C1 C6 C5 175.3(2) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C11 C5 C6 C1 179.2(2) . . . . ? C2 C3 C7 C8 -112.2(3) . . . . ? C4 C3 C7 C8 68.4(3) . . . . ? C2 C3 C7 C9 126.0(2) . . . . ? C4 C3 C7 C9 -53.4(3) . . . . ? C2 C3 C7 C10 8.1(3) . . . . ? C4 C3 C7 C10 -171.3(3) . . . . ? C6 C5 C11 C14 -7.6(4) . . . . ? C4 C5 C11 C14 172.4(3) . . . . ? C6 C5 C11 C13 111.7(3) . . . . ? C4 C5 C11 C13 -68.3(3) . . . . ? C6 C5 C11 C12 -125.6(3) . . . . ? C4 C5 C11 C12 54.4(4) . . . . ? C6 C1 C15 C16 137.2(2) . . . . ? C2 C1 C15 C16 -45.6(3) . . . . ? C6 C1 C15 C22 -94.2(3) . . . . ? C2 C1 C15 C22 82.9(3) . . . . ? C1 C15 C16 C21 110.9(3) . . . . ? C22 C15 C16 C21 -16.0(3) . . . . ? C1 C15 C16 C17 -69.9(3) . . . . ? C22 C15 C16 C17 163.2(2) . . . . ? C21 C16 C17 C18 -0.9(4) . . . . ? C15 C16 C17 C18 179.8(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C17 C18 C19 C20 1.4(5) . . . . ? C18 C19 C20 C21 -1.8(5) . . . . ? C17 C16 C21 C20 0.5(4) . . . . ? C15 C16 C21 C20 179.7(3) . . . . ? C19 C20 C21 C16 0.9(5) . . . . ? C16 C15 C22 C23 -172.12(19) . . . . ? C1 C15 C22 C23 59.9(3) . . . . ? C15 C22 C23 N1 65.9(3) . . . . ? C15 C22 C23 C24 -113.1(3) . . . . ? N1 C23 C24 C25 -0.2(5) . . . . ? C22 C23 C24 C25 178.8(3) . . . . ? C23 C24 C25 C26 1.2(6) . . . . ? C24 C25 C26 C27 -2.1(7) . . . . ? C25 C26 C27 N1 2.3(7) . . . . ? C24 C23 N1 C27 0.3(5) . . . . ? C22 C23 N1 C27 -178.8(3) . . . . ? C26 C27 N1 C23 -1.3(6) . . . . ?