#------------------------------------------------------------------------------ #$Date: 2023-02-03 04:11:54 +0200 (Fri, 03 Feb 2023) $ #$Revision: 280776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246236.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_7246236 loop_ _publ_author_name 'Ali, Akbar' 'Din, Zia Ud' 'Ibrahim, Muhammad' 'Ashfaq, Muhammad' 'Muhammad, Shabbir' 'Gull, Dania' 'Tahir, Muhammad Nawaz' 'Rodrigues-Filho, Edson' 'Al-Sehemi, Abdullah G.' 'Suleman, Muhammad' _publ_section_title ; Acid catalyzed one-pot approach towards the synthesis of curcuminoid systems: unsymmetrical diarylidene cycloalkanones, exploration of their single crystals, optical and nonlinear optical properties ; _journal_issue 7 _journal_name_full 'RSC Advances' _journal_page_first 4476 _journal_page_last 4494 _journal_paper_doi 10.1039/D2RA07681K _journal_volume 13 _journal_year 2023 _chemical_formula_iupac 'C19 H15 N O4' _chemical_formula_moiety 'C19 H15 N O4' _chemical_formula_sum 'C19 H15 N O4' _chemical_formula_weight 321.32 _chemical_name_systematic ; (3E,5E)-3-benzylidene-5-(4-nitrobenzylidene)dihydro-2H-pyran-4(3H)-one ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2022-05-11 deposited with the CCDC. 2023-01-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.5070(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5877(4) _cell_length_b 7.2192(4) _cell_length_c 28.0023(14) _cell_measurement_reflns_used 2850 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.729 _cell_measurement_theta_min 1.454 _cell_volume 1533.83(14) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2015 (Sheldrick, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.901 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_unetI/netI 0.0107 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 24896 _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 26.729 _diffrn_reflns_theta_min 1.454 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.381 _exptl_crystal_size_mid 0.375 _exptl_crystal_size_min 0.186 _refine_diff_density_max 0.189 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3262 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0413 _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^)+(0.0472P)^2^+0.5545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.1095 _reflns_number_gt 2850 _reflns_number_total 3262 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d2ra07681k2.cif _cod_data_source_block A1K7A11 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7246236 _shelx_shelxl_version_number 2019/2 _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_res_file ; TITL A1K7A11 in P2(1)/n shelx.res created by SHELXL-2019/2 at 18:18:22 on 26-Apr-2022 CELL 0.71073 7.5877 7.2192 28.0023 90.000 90.507 90.000 ZERR 4.00 0.0004 0.0004 0.0014 0.000 0.001 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 76 60 4 16 ACTA L.S. 40 HTAB 2.00000 BOND $H CONF TEMP 23.00 MERG 2 FMAP 2 PLAN 6 EQIV $1 x-1, y, z HTAB C5 O3_$1 EQIV $2 x+1, y, z HTAB C2 O1_$2 SIZE 0.186 0.375 0.381 WGHT 0.047200 0.554500 FVAR 0.16765 O1 4 -0.325083 0.697560 -0.153872 11.00000 0.04099 0.09542 = 0.07425 0.00368 -0.01548 0.01159 O2 4 -0.161149 0.525507 -0.197513 11.00000 0.07127 0.10465 = 0.06299 -0.02558 -0.02917 0.01273 O3 4 0.709997 0.781181 0.010368 11.00000 0.03578 0.13285 = 0.04383 -0.02216 0.00326 -0.00636 O4 4 0.305389 0.682852 0.094109 11.00000 0.04801 0.07441 = 0.03933 0.01282 -0.00398 -0.02185 N1 3 -0.185612 0.620422 -0.162331 11.00000 0.04434 0.05986 = 0.04953 0.00566 -0.01276 -0.00075 C1 1 0.235460 0.692753 -0.064423 11.00000 0.03478 0.03952 = 0.03616 0.00280 -0.00148 -0.00059 C2 1 0.264125 0.619739 -0.109696 11.00000 0.03457 0.04742 = 0.04145 -0.00246 0.00103 0.00307 AFIX 43 H2 2 0.378162 0.588637 -0.118585 11.00000 -1.20000 AFIX 0 C3 1 0.127246 0.592442 -0.141690 11.00000 0.04354 0.04604 = 0.03738 -0.00402 -0.00284 0.00177 AFIX 43 H3 2 0.147391 0.541166 -0.171616 11.00000 -1.20000 AFIX 0 C4 1 -0.039524 0.642984 -0.128181 11.00000 0.03638 0.04132 = 0.04022 0.00662 -0.00707 -0.00272 C5 1 -0.073718 0.717656 -0.084237 11.00000 0.03284 0.06023 = 0.04316 0.00350 0.00111 0.00425 AFIX 43 H5 2 -0.187833 0.751522 -0.076101 11.00000 -1.20000 AFIX 0 C6 1 0.063672 0.741843 -0.052245 11.00000 0.03925 0.06020 = 0.03499 -0.00120 0.00078 0.00602 AFIX 43 H6 2 0.041600 0.791403 -0.022231 11.00000 -1.20000 AFIX 0 C7 1 0.389334 0.721703 -0.033360 11.00000 0.03304 0.04725 = 0.04048 -0.00190 -0.00112 0.00149 AFIX 43 H7 2 0.496814 0.723396 -0.049062 11.00000 -1.20000 AFIX 0 C8 1 0.400327 0.746021 0.013774 11.00000 0.03433 0.04132 = 0.03889 0.00132 -0.00239 -0.00070 C9 1 0.578611 0.782841 0.035075 11.00000 0.03459 0.05230 = 0.03910 -0.00112 -0.00018 -0.00067 C10 1 0.588923 0.827200 0.086856 11.00000 0.03629 0.04040 = 0.03501 0.00196 -0.00052 0.00010 C11 1 0.419954 0.817722 0.114326 11.00000 0.03915 0.06257 = 0.03662 0.00192 0.00006 -0.00639 AFIX 23 H11A 2 0.445436 0.786103 0.147338 11.00000 -1.20000 H11B 2 0.362768 0.937884 0.113781 11.00000 -1.20000 AFIX 0 C12 1 0.248381 0.737321 0.047741 11.00000 0.03712 0.07083 = 0.03901 0.00596 -0.00224 -0.00965 AFIX 23 H12A 2 0.192562 0.857981 0.049484 11.00000 -1.20000 H12B 2 0.161719 0.649494 0.035877 11.00000 -1.20000 AFIX 0 C13 1 0.747772 0.864769 0.105602 11.00000 0.03601 0.04315 = 0.03833 0.00075 0.00123 -0.00083 AFIX 43 H13 2 0.840759 0.853469 0.084384 11.00000 -1.20000 AFIX 0 C14 1 0.799210 0.920557 0.153853 11.00000 0.03982 0.03814 = 0.03669 0.00360 -0.00198 -0.00559 C15 1 0.973621 0.890803 0.168012 11.00000 0.04009 0.05665 = 0.04554 -0.00048 -0.00224 -0.00499 AFIX 43 H15 2 1.050513 0.832369 0.147173 11.00000 -1.20000 AFIX 0 C16 1 1.034121 0.946276 0.212241 11.00000 0.05112 0.07292 = 0.05216 0.00093 -0.01463 -0.00903 AFIX 43 H16 2 1.150418 0.923623 0.221233 11.00000 -1.20000 AFIX 0 C17 1 0.922755 1.034954 0.243023 11.00000 0.07929 0.06245 = 0.04059 -0.00352 -0.01426 -0.00979 AFIX 43 H17 2 0.963743 1.073189 0.272828 11.00000 -1.20000 AFIX 0 C18 1 0.750638 1.067366 0.229861 11.00000 0.07802 0.04775 = 0.04118 -0.00213 0.00408 0.00312 AFIX 43 H18 2 0.675650 1.127991 0.250797 11.00000 -1.20000 AFIX 0 C19 1 0.688142 1.010506 0.185724 11.00000 0.04881 0.04324 = 0.04388 0.00176 -0.00097 0.00322 AFIX 43 H19 2 0.571210 1.032422 0.177244 11.00000 -1.20000 AFIX 0 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM A1K7A11 in P2(1)/n REM wR2 = 0.1095, GooF = S = 1.029, Restrained GooF = 1.029 for all data REM R1 = 0.0413 for 2850 Fo > 4sig(Fo) and 0.0474 for all 3262 data REM 217 parameters refined using 0 restraints END WGHT 0.0472 0.5545 REM Instructions for potential hydrogen bonds HTAB C5 O3_$1 REM Highest difference peak 0.189, deepest hole -0.189, 1-sigma level 0.033 Q1 1 0.5789 0.8089 0.0637 11.00000 0.05 0.19 Q2 1 0.4789 0.7754 0.0238 11.00000 0.05 0.19 Q3 1 0.3843 0.6702 -0.0056 11.00000 0.05 0.17 Q4 1 0.7296 0.9089 0.1736 11.00000 0.05 0.17 Q5 1 0.3783 0.8035 -0.0094 11.00000 0.05 0.16 Q6 1 0.3014 0.6734 -0.0445 11.00000 0.05 0.16 ; _shelx_res_checksum 38623 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 O1 O -0.32508(16) 0.6976(2) -0.15387(5) 0.0703(4) Uani 1 1 d . . . . . O2 O -0.16115(18) 0.5255(2) -0.19751(5) 0.0798(4) Uani 1 1 d . . . . . O3 O 0.71000(14) 0.7812(2) 0.01037(4) 0.0708(4) Uani 1 1 d . . . . . O4 O 0.30539(14) 0.68285(17) 0.09411(4) 0.0539(3) Uani 1 1 d . . . . . N1 N -0.18561(17) 0.6204(2) -0.16233(5) 0.0513(3) Uani 1 1 d . . . . . C1 C 0.23546(17) 0.69275(19) -0.06442(5) 0.0368(3) Uani 1 1 d . . . . . C2 C 0.26412(18) 0.6197(2) -0.10970(5) 0.0411(3) Uani 1 1 d . . . . . H2 H 0.378162 0.588637 -0.118585 0.049 Uiso 1 1 calc R U . . . C3 C 0.12725(19) 0.5924(2) -0.14169(5) 0.0423(3) Uani 1 1 d . . . . . H3 H 0.147391 0.541166 -0.171616 0.051 Uiso 1 1 calc R U . . . C4 C -0.03952(18) 0.64298(19) -0.12818(5) 0.0393(3) Uani 1 1 d . . . . . C5 C -0.07372(19) 0.7177(2) -0.08424(5) 0.0454(3) Uani 1 1 d . . . . . H5 H -0.187833 0.751522 -0.076101 0.054 Uiso 1 1 calc R U . . . C6 C 0.06367(19) 0.7418(2) -0.05224(5) 0.0448(3) Uani 1 1 d . . . . . H6 H 0.041600 0.791403 -0.022231 0.054 Uiso 1 1 calc R U . . . C7 C 0.38933(18) 0.7217(2) -0.03336(5) 0.0403(3) Uani 1 1 d . . . . . H7 H 0.496814 0.723396 -0.049062 0.048 Uiso 1 1 calc R U . . . C8 C 0.40033(17) 0.74602(19) 0.01377(5) 0.0382(3) Uani 1 1 d . . . . . C9 C 0.57861(18) 0.7828(2) 0.03507(5) 0.0420(3) Uani 1 1 d . . . . . C10 C 0.58892(18) 0.82720(19) 0.08686(5) 0.0372(3) Uani 1 1 d . . . . . C11 C 0.41995(19) 0.8177(2) 0.11433(5) 0.0461(4) Uani 1 1 d . . . . . H11A H 0.445436 0.786103 0.147338 0.055 Uiso 1 1 calc R U . . . H11B H 0.362768 0.937884 0.113781 0.055 Uiso 1 1 calc R U . . . C12 C 0.24838(19) 0.7373(3) 0.04774(5) 0.0490(4) Uani 1 1 d . . . . . H12A H 0.192562 0.857981 0.049484 0.059 Uiso 1 1 calc R U . . . H12B H 0.161719 0.649494 0.035877 0.059 Uiso 1 1 calc R U . . . C13 C 0.74777(18) 0.86477(19) 0.10560(5) 0.0392(3) Uani 1 1 d . . . . . H13 H 0.840759 0.853469 0.084384 0.047 Uiso 1 1 calc R U . . . C14 C 0.79921(18) 0.92056(19) 0.15385(5) 0.0382(3) Uani 1 1 d . . . . . C15 C 0.9736(2) 0.8908(2) 0.16801(5) 0.0474(4) Uani 1 1 d . . . . . H15 H 1.050513 0.832369 0.147173 0.057 Uiso 1 1 calc R U . . . C16 C 1.0341(2) 0.9463(3) 0.21224(6) 0.0588(4) Uani 1 1 d . . . . . H16 H 1.150418 0.923623 0.221233 0.071 Uiso 1 1 calc R U . . . C17 C 0.9228(3) 1.0350(3) 0.24302(6) 0.0609(5) Uani 1 1 d . . . . . H17 H 0.963743 1.073189 0.272828 0.073 Uiso 1 1 calc R U . . . C18 C 0.7506(3) 1.0674(2) 0.22986(6) 0.0556(4) Uani 1 1 d . . . . . H18 H 0.675650 1.127991 0.250797 0.067 Uiso 1 1 calc R U . . . C19 C 0.6881(2) 1.0105(2) 0.18572(5) 0.0453(3) Uani 1 1 d . . . . . H19 H 0.571210 1.032422 0.177244 0.054 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 O1 0.0410(6) 0.0954(10) 0.0742(9) 0.0037(7) -0.0155(6) 0.0116(7) O2 0.0713(9) 0.1046(11) 0.0630(8) -0.0256(8) -0.0292(7) 0.0127(8) O3 0.0358(6) 0.1329(13) 0.0438(6) -0.0222(7) 0.0033(5) -0.0064(7) O4 0.0480(6) 0.0744(8) 0.0393(5) 0.0128(5) -0.0040(4) -0.0218(5) N1 0.0443(7) 0.0599(8) 0.0495(7) 0.0057(6) -0.0128(6) -0.0007(6) C1 0.0348(7) 0.0395(7) 0.0362(7) 0.0028(5) -0.0015(5) -0.0006(5) C2 0.0346(7) 0.0474(8) 0.0415(7) -0.0025(6) 0.0010(6) 0.0031(6) C3 0.0435(8) 0.0460(8) 0.0374(7) -0.0040(6) -0.0028(6) 0.0018(6) C4 0.0364(7) 0.0413(7) 0.0402(7) 0.0066(6) -0.0071(6) -0.0027(6) C5 0.0328(7) 0.0602(9) 0.0432(8) 0.0035(7) 0.0011(6) 0.0042(6) C6 0.0392(8) 0.0602(9) 0.0350(7) -0.0012(6) 0.0008(6) 0.0060(7) C7 0.0330(7) 0.0472(8) 0.0405(7) -0.0019(6) -0.0011(5) 0.0015(6) C8 0.0343(7) 0.0413(7) 0.0389(7) 0.0013(6) -0.0024(5) -0.0007(6) C9 0.0346(7) 0.0523(8) 0.0391(7) -0.0011(6) -0.0002(6) -0.0007(6) C10 0.0363(7) 0.0404(7) 0.0350(7) 0.0020(5) -0.0005(5) 0.0001(6) C11 0.0391(8) 0.0626(9) 0.0366(7) 0.0019(7) 0.0001(6) -0.0064(7) C12 0.0371(8) 0.0708(10) 0.0390(7) 0.0060(7) -0.0022(6) -0.0097(7) C13 0.0360(7) 0.0431(7) 0.0383(7) 0.0008(6) 0.0012(5) -0.0008(6) C14 0.0398(7) 0.0381(7) 0.0367(7) 0.0036(5) -0.0020(5) -0.0056(6) C15 0.0401(8) 0.0566(9) 0.0455(8) -0.0005(7) -0.0022(6) -0.0050(7) C16 0.0511(9) 0.0729(11) 0.0522(9) 0.0009(8) -0.0146(7) -0.0090(8) C17 0.0793(12) 0.0625(11) 0.0406(8) -0.0035(8) -0.0143(8) -0.0098(9) C18 0.0780(12) 0.0478(9) 0.0412(8) -0.0021(7) 0.0041(8) 0.0031(8) C19 0.0488(8) 0.0432(8) 0.0439(8) 0.0018(6) -0.0010(6) 0.0032(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 C11 O4 C12 110.80(12) . . ? O2 N1 O1 123.58(14) . . ? O2 N1 C4 118.10(13) . . ? O1 N1 C4 118.31(14) . . ? C2 C1 C6 118.19(12) . . ? C2 C1 C7 117.70(12) . . ? C6 C1 C7 124.04(13) . . ? C3 C2 C1 121.52(13) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 118.25(13) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C4 C3 122.28(13) . . ? C5 C4 N1 118.76(13) . . ? C3 C4 N1 118.94(13) . . ? C4 C5 C6 119.01(13) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 120.74(13) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C1 130.48(13) . . ? C8 C7 H7 114.8 . . ? C1 C7 H7 114.8 . . ? C7 C8 C9 117.78(13) . . ? C7 C8 C12 125.42(13) . . ? C9 C8 C12 116.80(12) . . ? O3 C9 C10 121.31(13) . . ? O3 C9 C8 120.85(13) . . ? C10 C9 C8 117.80(12) . . ? C13 C10 C9 117.76(12) . . ? C13 C10 C11 125.32(13) . . ? C9 C10 C11 116.86(12) . . ? O4 C11 C10 110.45(12) . . ? O4 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? O4 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O4 C12 C8 111.17(12) . . ? O4 C12 H12A 109.4 . . ? C8 C12 H12A 109.4 . . ? O4 C12 H12B 109.4 . . ? C8 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C10 C13 C14 130.66(13) . . ? C10 C13 H13 114.7 . . ? C14 C13 H13 114.7 . . ? C19 C14 C15 117.87(13) . . ? C19 C14 C13 124.27(13) . . ? C15 C14 C13 117.77(13) . . ? C16 C15 C14 121.26(15) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 119.93(16) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.04(15) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.47(16) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.43(15) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? 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 O1 N1 1.2209(18) . ? O2 N1 1.2156(18) . ? O3 C9 1.2185(18) . ? O4 C11 1.4197(18) . ? O4 C12 1.4204(17) . ? N1 C4 1.4666(18) . ? C1 C2 1.3918(19) . ? C1 C6 1.3960(19) . ? C1 C7 1.4647(18) . ? C2 C3 1.3798(19) . ? C2 H2 0.9300 . ? C3 C4 1.373(2) . ? C3 H3 0.9300 . ? C4 C5 1.370(2) . ? C5 C6 1.380(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.3334(19) . ? C7 H7 0.9300 . ? C8 C9 1.4974(19) . ? C8 C12 1.502(2) . ? C9 C10 1.4863(19) . ? C10 C13 1.3382(19) . ? C10 C11 1.5025(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.4597(19) . ? C13 H13 0.9300 . ? C14 C19 1.393(2) . ? C14 C15 1.395(2) . ? C15 C16 1.377(2) . ? C15 H15 0.9300 . ? C16 C17 1.371(3) . ? C16 H16 0.9300 . ? C17 C18 1.374(3) . ? C17 H17 0.9300 . ? C18 C19 1.382(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? 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 C5 H5 O3 0.93 2.56 3.1620(18) 123.0 1_455 yes C2 H2 O1 0.93 2.59 3.4102(19) 147.5 1_655 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 -1.3(2) . . . . ? C7 C1 C2 C3 -178.32(13) . . . . ? C1 C2 C3 C4 1.4(2) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 N1 178.06(13) . . . . ? O2 N1 C4 C5 -167.28(16) . . . . ? O1 N1 C4 C5 12.6(2) . . . . ? O2 N1 C4 C3 14.1(2) . . . . ? O1 N1 C4 C3 -165.99(15) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? N1 C4 C5 C6 -179.01(14) . . . . ? C4 C5 C6 C1 0.6(2) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C7 C1 C6 C5 177.14(14) . . . . ? C2 C1 C7 C8 -162.09(15) . . . . ? C6 C1 C7 C8 21.0(2) . . . . ? C1 C7 C8 C9 -176.74(14) . . . . ? C1 C7 C8 C12 4.1(3) . . . . ? C7 C8 C9 O3 -3.6(2) . . . . ? C12 C8 C9 O3 175.64(16) . . . . ? C7 C8 C9 C10 174.46(13) . . . . ? C12 C8 C9 C10 -6.3(2) . . . . ? O3 C9 C10 C13 -0.2(2) . . . . ? C8 C9 C10 C13 -178.32(13) . . . . ? O3 C9 C10 C11 -177.59(16) . . . . ? C8 C9 C10 C11 4.3(2) . . . . ? C12 O4 C11 C10 -66.43(16) . . . . ? C13 C10 C11 O4 -146.79(14) . . . . ? C9 C10 C11 O4 30.34(18) . . . . ? C11 O4 C12 C8 64.52(17) . . . . ? C7 C8 C12 O4 152.65(15) . . . . ? C9 C8 C12 O4 -26.6(2) . . . . ? C9 C10 C13 C14 176.86(14) . . . . ? C11 C10 C13 C14 -6.0(3) . . . . ? C10 C13 C14 C19 -24.8(2) . . . . ? C10 C13 C14 C15 158.80(15) . . . . ? C19 C14 C15 C16 0.8(2) . . . . ? C13 C14 C15 C16 177.39(15) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C14 -0.4(2) . . . . ? C15 C14 C19 C18 -0.1(2) . . . . ? C13 C14 C19 C18 -176.47(14) . . . . ?