#------------------------------------------------------------------------------ #$Date: 2023-11-23 04:12:11 +0200 (Thu, 23 Nov 2023) $ #$Revision: 287751 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247780.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_7247780 loop_ _publ_author_name 'Takkar, Priya' 'Singh, Bholey' 'Pani, Balaram' 'Kumar, Rakesh' _publ_section_title ; Design, synthesis and in silico evaluation of newer 1,4-dihydropyridine based amlodipine bio-isosteres as promising antihypertensive agents ; _journal_issue 48 _journal_name_full 'RSC Advances' _journal_page_first 34239 _journal_page_last 34248 _journal_paper_doi 10.1039/D3RA06387A _journal_volume 13 _journal_year 2023 _chemical_formula_sum 'C3.87 H4.13 Cl0.13 F0.13 N0.52 O0.65' _chemical_formula_weight 75.23 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2023-09-13 deposited with the CCDC. 2023-11-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.890(4) _cell_angle_gamma 90 _cell_formula_units_Z 31 _cell_length_a 9.5711(4) _cell_length_b 37.8741(14) _cell_length_c 7.8420(3) _cell_measurement_reflns_used 12140 _cell_measurement_temperature 107(2) _cell_measurement_theta_max 31.1620 _cell_measurement_theta_min 3.416 _cell_volume 2781.71(19) _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _diffrn_ambient_temperature 107(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.797 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.797 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 22390 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.797 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.063 _diffrn_reflns_theta_min 3.059 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellowish _exptl_crystal_density_diffrn 1.392 _exptl_crystal_description rectangular _exptl_crystal_F_000 1224 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethanol' _refine_diff_density_max 1.029 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 371 _refine_ls_number_reflns 7106 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0468 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+1.0253P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1233 _refine_ls_wR_factor_ref 0.1304 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5657 _reflns_number_total 7106 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06387a2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247780 _shelx_shelxl_version_number 2016/4 _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 shelxt_a.res in P2(1)/c shelx.res created by SHELXL-2016/4 at 11:56:44 on 07-Sep-2023 CELL 0.71073 9.5711 37.8741 7.8420 90.000 101.890 90.000 ZERR 31.00 0.0004 0.0014 0.0003 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F CL UNIT 120 128 16 20 4 4 MERG 2 MORE -1 FMAP 2 PLAN 1 ACTA BOND $H CONF LIST 6 L.S. 10 TEMP -166.00 WGHT 0.062600 1.025300 FVAR 0.40503 CL 6 0.360950 0.716623 0.495741 11.00000 0.02447 0.01413 = 0.02727 -0.00388 0.00510 -0.00274 F 5 0.111308 0.277807 0.352611 11.00000 0.02973 0.01329 = 0.04281 -0.00043 0.01366 -0.00544 O4 4 0.528958 0.663002 0.263604 11.00000 0.01903 0.01246 = 0.02222 -0.00136 0.00885 -0.00249 O1 4 0.366558 0.519642 0.137321 11.00000 0.01892 0.01095 = 0.02227 -0.00073 0.00262 0.00001 O3 4 0.291096 0.658005 0.737407 11.00000 0.03276 0.01638 = 0.01816 -0.00254 0.01105 0.00054 O5 4 0.547862 0.616647 0.090692 11.00000 0.02957 0.01582 = 0.02820 -0.00335 0.01752 -0.00176 O2 4 0.197707 0.608992 0.832464 11.00000 0.03753 0.02309 = 0.02281 0.00242 0.01523 -0.00019 N4 3 0.296091 0.415470 0.333814 11.00000 0.01889 0.01237 = 0.01630 -0.00050 0.00420 0.00035 N1 3 0.293646 0.559360 0.377722 11.00000 0.01931 0.01179 = 0.01956 -0.00035 0.00693 -0.00179 AFIX 43 H1 2 0.263010 0.538039 0.344519 11.00000 -1.20000 AFIX 0 N2 3 0.309623 0.470175 0.404996 11.00000 0.02803 0.01564 = 0.02232 -0.00436 0.00845 -0.00249 N3 3 0.250814 0.440284 0.435144 11.00000 0.03003 0.01544 = 0.02251 -0.00539 0.01076 -0.00172 C00C 1 0.227516 0.656716 0.344302 11.00000 0.01442 0.01328 = 0.01588 -0.00012 0.00698 0.00090 C6 1 0.392782 0.464895 0.284736 11.00000 0.01829 0.01349 = 0.01813 -0.00057 0.00270 0.00076 C10 1 0.411604 0.611277 0.314166 11.00000 0.01405 0.01259 = 0.01590 0.00041 0.00313 0.00145 C00F 1 0.224945 0.693480 0.357543 11.00000 0.01733 0.01471 = 0.02009 -0.00097 0.00633 0.00039 C00G 1 0.249268 0.379831 0.339079 11.00000 0.01787 0.01242 = 0.01518 0.00047 0.00146 0.00049 C5 1 0.383881 0.430068 0.237100 11.00000 0.01718 0.01519 = 0.01794 0.00021 0.00441 0.00127 AFIX 43 H5 2 0.428922 0.418655 0.154920 11.00000 -1.20000 AFIX 0 C9 1 0.377219 0.576913 0.281831 11.00000 0.01417 0.01285 = 0.01813 0.00143 0.00340 0.00185 C16 1 0.502011 0.629250 0.211669 11.00000 0.01558 0.01307 = 0.02021 -0.00010 0.00459 0.00147 C3 1 0.313812 0.353431 0.258335 11.00000 0.01902 0.01532 = 0.01817 0.00078 0.00529 0.00011 AFIX 43 H3 2 0.388874 0.359053 0.200388 11.00000 -1.20000 AFIX 0 C11 1 0.346778 0.632769 0.443580 11.00000 0.01633 0.01161 = 0.01524 0.00156 0.00568 0.00280 C15 1 0.252278 0.623558 0.724535 11.00000 0.01825 0.01773 = 0.01667 0.00299 0.00344 0.00408 C12 1 0.286224 0.608029 0.565088 11.00000 0.01580 0.01508 = 0.01614 0.00297 0.00404 0.00298 C20 1 0.113188 0.640945 0.229628 11.00000 0.01728 0.01522 = 0.01831 -0.00057 0.00528 0.00123 AFIX 43 H20 2 0.111269 0.615972 0.218036 11.00000 -1.20000 AFIX 0 C00P 1 0.158262 0.311622 0.348663 11.00000 0.02132 0.01209 = 0.02373 0.00177 0.00396 -0.00215 C13 1 0.255565 0.573733 0.524134 11.00000 0.01491 0.01578 = 0.01727 0.00312 0.00351 0.00249 C00R 1 0.114706 0.713634 0.260994 11.00000 0.02482 0.01274 = 0.02845 0.00303 0.01003 0.00511 AFIX 43 H00R 2 0.115875 0.738609 0.272458 11.00000 -1.20000 AFIX 0 C2 1 0.267119 0.318864 0.263628 11.00000 0.02075 0.01483 = 0.02093 -0.00104 0.00457 0.00165 AFIX 43 H2 2 0.309636 0.300482 0.209393 11.00000 -1.20000 AFIX 0 C00T 1 0.002398 0.660611 0.132176 11.00000 0.01837 0.02053 = 0.02135 -0.00023 0.00291 0.00211 AFIX 43 H00T 2 -0.073657 0.649174 0.054963 11.00000 -1.20000 AFIX 0 C7 1 0.471065 0.495158 0.226729 11.00000 0.01805 0.01319 = 0.02043 -0.00071 0.00331 0.00053 AFIX 23 H7A 2 0.532303 0.506720 0.328560 11.00000 -1.20000 H7B 2 0.532509 0.486783 0.147755 11.00000 -1.20000 AFIX 0 C8 1 0.418965 0.554899 0.137387 11.00000 0.02230 0.01101 = 0.02221 -0.00145 0.00794 -0.00086 AFIX 23 H8A 2 0.379942 0.566025 0.023277 11.00000 -1.20000 H8B 2 0.524298 0.554402 0.153573 11.00000 -1.20000 AFIX 0 C14 1 0.181832 0.547997 0.622531 11.00000 0.02494 0.01701 = 0.02330 0.00347 0.01048 0.00068 AFIX 33 H14A 2 0.173659 0.525039 0.563673 11.00000 -1.50000 H14B 2 0.237549 0.545367 0.741554 11.00000 -1.50000 H14C 2 0.086307 0.556840 0.626398 11.00000 -1.50000 AFIX 0 C4 1 0.139728 0.371907 0.425798 11.00000 0.02325 0.01680 = 0.02713 -0.00183 0.01074 0.00056 AFIX 43 H4 2 0.097050 0.390114 0.480991 11.00000 -1.20000 AFIX 0 C00Y 1 0.003707 0.697213 0.148562 11.00000 0.02126 0.02161 = 0.02443 0.00483 0.00492 0.00783 AFIX 43 H00Y 2 -0.071655 0.710875 0.082491 11.00000 -1.20000 AFIX 0 C1 1 0.093494 0.337308 0.430978 11.00000 0.02165 0.01943 = 0.03012 0.00079 0.01122 -0.00166 AFIX 43 H1A 2 0.019169 0.331393 0.489617 11.00000 -1.20000 AFIX 0 C17 1 0.614319 0.682788 0.164118 11.00000 0.02426 0.01602 = 0.03368 -0.00060 0.01654 -0.00458 AFIX 23 H17A 2 0.569627 0.681998 0.038539 11.00000 -1.20000 H17B 2 0.711174 0.672459 0.180223 11.00000 -1.20000 AFIX 0 C18 1 0.623175 0.720285 0.228137 11.00000 0.02882 0.01501 = 0.03419 0.00117 0.00994 -0.00321 AFIX 33 H18A 2 0.680540 0.734230 0.162641 11.00000 -1.50000 H18B 2 0.526870 0.730291 0.211179 11.00000 -1.50000 H18C 2 0.667892 0.720787 0.352338 11.00000 -1.50000 AFIX 0 C19 1 0.252014 0.677624 0.877632 11.00000 0.03510 0.02201 = 0.01886 -0.00413 0.00944 0.00353 AFIX 33 H19A 2 0.285115 0.702059 0.874675 11.00000 -1.50000 H19B 2 0.147956 0.677368 0.864527 11.00000 -1.50000 H19C 2 0.296357 0.666804 0.989191 11.00000 -1.50000 AFIX 0 C21 1 0.029649 0.491172 -0.069637 11.00000 0.02497 0.03351 = 0.02348 0.00078 0.00357 -0.00844 AFIX 23 H21A 2 0.124297 0.501463 -0.072085 11.00000 -1.20000 H21B 2 -0.033949 0.495905 -0.183841 11.00000 -1.20000 AFIX 0 C22 1 0.045299 0.451777 -0.043812 11.00000 0.03019 0.04002 = 0.03425 0.00081 -0.00076 -0.00012 AFIX 23 H22A 2 -0.050300 0.440854 -0.056965 11.00000 -1.20000 H22B 2 0.099475 0.446750 0.075458 11.00000 -1.20000 AFIX 0 C23 1 0.123710 0.435763 -0.177629 11.00000 0.04139 0.06255 = 0.05477 -0.00669 0.00777 0.00023 AFIX 137 H23A 2 0.061134 0.436347 -0.293483 11.00000 -1.50000 H23B 2 0.149738 0.411262 -0.145627 11.00000 -1.50000 H23C 2 0.210311 0.449457 -0.179199 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0468 for 5657 Fo > 4sig(Fo) and 0.0603 for all 7106 data REM 371 parameters refined using 0 restraints END WGHT 0.0625 1.0272 REM Highest difference peak 1.029, deepest hole -0.516, 1-sigma level 0.064 Q1 1 -0.0017 0.4404 0.0373 11.00000 0.05 1.03 ; _shelx_res_checksum 98663 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 CL Cl 0.36095(4) 0.71662(2) 0.49574(5) 0.02199(11) Uani 1 1 d . . . . . F F 0.11131(12) 0.27781(3) 0.35261(15) 0.0277(2) Uani 1 1 d . . . . . O4 O 0.52896(12) 0.66300(3) 0.26360(15) 0.0172(2) Uani 1 1 d . . . . . O1 O 0.36656(12) 0.51964(3) 0.13732(15) 0.0176(2) Uani 1 1 d . . . . . O3 O 0.29110(14) 0.65801(3) 0.73741(15) 0.0216(3) Uani 1 1 d . . . . . O5 O 0.54786(13) 0.61665(3) 0.09069(16) 0.0229(3) Uani 1 1 d . . . . . O2 O 0.19771(15) 0.60899(3) 0.83246(16) 0.0265(3) Uani 1 1 d . . . . . N4 N 0.29609(14) 0.41547(3) 0.33381(17) 0.0158(3) Uani 1 1 d . . . . . N1 N 0.29365(14) 0.55936(3) 0.37772(17) 0.0165(3) Uani 1 1 d . . . . . H1 H 0.263010 0.538039 0.344519 0.020 Uiso 1 1 calc R U . . . N2 N 0.30962(16) 0.47018(4) 0.40500(19) 0.0215(3) Uani 1 1 d . . . . . N3 N 0.25081(16) 0.44028(4) 0.43514(19) 0.0219(3) Uani 1 1 d . . . . . C00C C 0.22752(16) 0.65672(4) 0.34430(19) 0.0140(3) Uani 1 1 d . . . . . C6 C 0.39278(17) 0.46489(4) 0.2847(2) 0.0168(3) Uani 1 1 d . . . . . C10 C 0.41160(16) 0.61128(4) 0.3142(2) 0.0142(3) Uani 1 1 d . . . . . C00F C 0.22494(17) 0.69348(4) 0.3575(2) 0.0170(3) Uani 1 1 d . . . . . C00G C 0.24927(17) 0.37983(4) 0.3391(2) 0.0154(3) Uani 1 1 d . . . . . C5 C 0.38388(17) 0.43007(4) 0.2371(2) 0.0167(3) Uani 1 1 d . . . . . H5 H 0.428922 0.418655 0.154920 0.020 Uiso 1 1 calc R U . . . C9 C 0.37722(16) 0.57691(4) 0.2818(2) 0.0150(3) Uani 1 1 d . . . . . C16 C 0.50201(17) 0.62925(4) 0.2117(2) 0.0162(3) Uani 1 1 d . . . . . C3 C 0.31381(17) 0.35343(4) 0.2583(2) 0.0173(3) Uani 1 1 d . . . . . H3 H 0.388874 0.359053 0.200388 0.021 Uiso 1 1 calc R U . . . C11 C 0.34678(17) 0.63277(4) 0.4436(2) 0.0140(3) Uani 1 1 d . . . . . C15 C 0.25228(17) 0.62356(4) 0.7245(2) 0.0176(3) Uani 1 1 d . . . . . C12 C 0.28622(17) 0.60803(4) 0.5651(2) 0.0156(3) Uani 1 1 d . . . . . C20 C 0.11319(17) 0.64094(4) 0.2296(2) 0.0167(3) Uani 1 1 d . . . . . H20 H 0.111269 0.615972 0.218036 0.020 Uiso 1 1 calc R U . . . C00P C 0.15826(18) 0.31162(4) 0.3487(2) 0.0191(3) Uani 1 1 d . . . . . C13 C 0.25556(17) 0.57373(4) 0.5241(2) 0.0160(3) Uani 1 1 d . . . . . C00R C 0.11471(19) 0.71363(4) 0.2610(2) 0.0214(3) Uani 1 1 d . . . . . H00R H 0.115875 0.738609 0.272458 0.026 Uiso 1 1 calc R U . . . C2 C 0.26712(18) 0.31886(4) 0.2636(2) 0.0188(3) Uani 1 1 d . . . . . H2 H 0.309636 0.300482 0.209393 0.023 Uiso 1 1 calc R U . . . C00T C 0.00240(18) 0.66061(4) 0.1322(2) 0.0203(3) Uani 1 1 d . . . . . H00T H -0.073657 0.649174 0.054963 0.024 Uiso 1 1 calc R U . . . C7 C 0.47107(17) 0.49516(4) 0.2267(2) 0.0173(3) Uani 1 1 d . . . . . H7A H 0.532303 0.506720 0.328560 0.021 Uiso 1 1 calc R U . . . H7B H 0.532509 0.486783 0.147755 0.021 Uiso 1 1 calc R U . . . C8 C 0.41897(18) 0.55490(4) 0.1374(2) 0.0180(3) Uani 1 1 d . . . . . H8A H 0.379942 0.566025 0.023277 0.022 Uiso 1 1 calc R U . . . H8B H 0.524298 0.554402 0.153573 0.022 Uiso 1 1 calc R U . . . C14 C 0.18183(19) 0.54800(4) 0.6225(2) 0.0210(3) Uani 1 1 d . . . . . H14A H 0.173659 0.525039 0.563673 0.031 Uiso 1 1 calc R U . . . H14B H 0.237549 0.545367 0.741554 0.031 Uiso 1 1 calc R U . . . H14C H 0.086307 0.556840 0.626398 0.031 Uiso 1 1 calc R U . . . C4 C 0.13973(19) 0.37191(4) 0.4258(2) 0.0216(3) Uani 1 1 d . . . . . H4 H 0.097050 0.390114 0.480991 0.026 Uiso 1 1 calc R U . . . C00Y C 0.00371(18) 0.69721(5) 0.1486(2) 0.0224(3) Uani 1 1 d . . . . . H00Y H -0.071655 0.710875 0.082491 0.027 Uiso 1 1 calc R U . . . C1 C 0.09349(19) 0.33731(4) 0.4310(2) 0.0229(4) Uani 1 1 d . . . . . H1A H 0.019169 0.331393 0.489617 0.027 Uiso 1 1 calc R U . . . C17 C 0.61432(19) 0.68279(4) 0.1641(2) 0.0231(4) Uani 1 1 d . . . . . H17A H 0.569627 0.681998 0.038539 0.028 Uiso 1 1 calc R U . . . H17B H 0.711174 0.672459 0.180223 0.028 Uiso 1 1 calc R U . . . C18 C 0.6232(2) 0.72029(4) 0.2281(3) 0.0255(4) Uani 1 1 d . . . . . H18A H 0.680540 0.734230 0.162641 0.038 Uiso 1 1 calc R U . . . H18B H 0.526870 0.730291 0.211179 0.038 Uiso 1 1 calc R U . . . H18C H 0.667892 0.720787 0.352338 0.038 Uiso 1 1 calc R U . . . C19 C 0.2520(2) 0.67762(5) 0.8776(2) 0.0248(4) Uani 1 1 d . . . . . H19A H 0.285115 0.702059 0.874675 0.037 Uiso 1 1 calc R U . . . H19B H 0.147956 0.677368 0.864527 0.037 Uiso 1 1 calc R U . . . H19C H 0.296357 0.666804 0.989191 0.037 Uiso 1 1 calc R U . . . C21 C 0.0296(2) 0.49117(5) -0.0696(2) 0.0275(4) Uani 1 1 d . . . . . H21A H 0.124297 0.501463 -0.072085 0.033 Uiso 1 1 calc R U . . . H21B H -0.033949 0.495905 -0.183841 0.033 Uiso 1 1 calc R U . . . C22 C 0.0453(2) 0.45178(6) -0.0438(3) 0.0359(5) Uani 1 1 d . . . . . H22A H -0.050300 0.440854 -0.056965 0.043 Uiso 1 1 calc R U . . . H22B H 0.099475 0.446750 0.075458 0.043 Uiso 1 1 calc R U . . . C23 C 0.1237(3) 0.43576(8) -0.1776(4) 0.0532(6) Uani 1 1 d . . . . . H23A H 0.061134 0.436347 -0.293483 0.080 Uiso 1 1 calc R U . . . H23B H 0.149738 0.411262 -0.145627 0.080 Uiso 1 1 calc R U . . . H23C H 0.210311 0.449457 -0.179199 0.080 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 CL 0.0245(2) 0.01413(19) 0.0273(2) -0.00388(14) 0.00510(16) -0.00274(14) F 0.0297(6) 0.0133(5) 0.0428(6) -0.0004(4) 0.0137(5) -0.0054(4) O4 0.0190(6) 0.0125(5) 0.0222(6) -0.0014(4) 0.0089(5) -0.0025(4) O1 0.0189(6) 0.0110(5) 0.0223(6) -0.0007(4) 0.0026(5) 0.0000(4) O3 0.0328(7) 0.0164(6) 0.0182(6) -0.0025(4) 0.0111(5) 0.0005(5) O5 0.0296(7) 0.0158(6) 0.0282(6) -0.0033(5) 0.0175(5) -0.0018(5) O2 0.0375(7) 0.0231(6) 0.0228(6) 0.0024(5) 0.0152(6) -0.0002(5) N4 0.0189(7) 0.0124(6) 0.0163(6) -0.0005(5) 0.0042(5) 0.0003(5) N1 0.0193(7) 0.0118(6) 0.0196(7) -0.0004(5) 0.0069(5) -0.0018(5) N2 0.0280(8) 0.0156(7) 0.0223(7) -0.0044(5) 0.0085(6) -0.0025(6) N3 0.0300(8) 0.0154(7) 0.0225(7) -0.0054(5) 0.0108(6) -0.0017(6) C00C 0.0144(7) 0.0133(7) 0.0159(7) -0.0001(5) 0.0070(6) 0.0009(5) C6 0.0183(8) 0.0135(7) 0.0181(7) -0.0006(6) 0.0027(6) 0.0008(6) C10 0.0141(7) 0.0126(7) 0.0159(7) 0.0004(5) 0.0031(6) 0.0015(5) C00F 0.0173(8) 0.0147(7) 0.0201(8) -0.0010(6) 0.0063(6) 0.0004(6) C00G 0.0179(8) 0.0124(7) 0.0152(7) 0.0005(5) 0.0015(6) 0.0005(6) C5 0.0172(8) 0.0152(7) 0.0179(7) 0.0002(6) 0.0044(6) 0.0013(6) C9 0.0142(7) 0.0128(7) 0.0181(7) 0.0014(5) 0.0034(6) 0.0019(5) C16 0.0156(7) 0.0131(7) 0.0202(8) -0.0001(6) 0.0046(6) 0.0015(6) C3 0.0190(8) 0.0153(7) 0.0182(7) 0.0008(6) 0.0053(6) 0.0001(6) C11 0.0163(7) 0.0116(7) 0.0152(7) 0.0016(5) 0.0057(6) 0.0028(5) C15 0.0183(8) 0.0177(8) 0.0167(7) 0.0030(6) 0.0034(6) 0.0041(6) C12 0.0158(7) 0.0151(7) 0.0161(7) 0.0030(6) 0.0040(6) 0.0030(6) C20 0.0173(8) 0.0152(7) 0.0183(7) -0.0006(6) 0.0053(6) 0.0012(6) C00P 0.0213(8) 0.0121(7) 0.0237(8) 0.0018(6) 0.0040(7) -0.0022(6) C13 0.0149(7) 0.0158(7) 0.0173(7) 0.0031(6) 0.0035(6) 0.0025(6) C00R 0.0248(9) 0.0127(7) 0.0285(9) 0.0030(6) 0.0100(7) 0.0051(6) C2 0.0208(8) 0.0148(7) 0.0209(8) -0.0010(6) 0.0046(6) 0.0016(6) C00T 0.0184(8) 0.0205(8) 0.0213(8) -0.0002(6) 0.0029(6) 0.0021(6) C7 0.0181(8) 0.0132(7) 0.0204(8) -0.0007(6) 0.0033(6) 0.0005(6) C8 0.0223(8) 0.0110(7) 0.0222(8) -0.0015(6) 0.0079(7) -0.0009(6) C14 0.0249(9) 0.0170(8) 0.0233(8) 0.0035(6) 0.0105(7) 0.0007(6) C4 0.0232(8) 0.0168(8) 0.0271(9) -0.0018(6) 0.0107(7) 0.0006(6) C00Y 0.0213(8) 0.0216(8) 0.0244(8) 0.0048(6) 0.0049(7) 0.0078(7) C1 0.0217(8) 0.0194(8) 0.0301(9) 0.0008(7) 0.0112(7) -0.0017(6) C17 0.0243(9) 0.0160(8) 0.0337(9) -0.0006(7) 0.0165(7) -0.0046(6) C18 0.0288(9) 0.0150(8) 0.0342(10) 0.0012(7) 0.0099(8) -0.0032(7) C19 0.0351(10) 0.0220(9) 0.0189(8) -0.0041(6) 0.0094(7) 0.0035(7) C21 0.0250(9) 0.0335(10) 0.0235(9) 0.0008(7) 0.0036(7) -0.0084(7) C22 0.0302(10) 0.0400(12) 0.0343(11) 0.0008(9) -0.0008(8) -0.0001(9) C23 0.0414(13) 0.0626(17) 0.0548(16) -0.0067(12) 0.0078(12) 0.0002(12) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C16 O4 C17 114.90(12) . . ? C8 O1 C7 113.25(12) . . ? C15 O3 C19 116.35(13) . . ? N3 N4 C5 110.69(13) . . ? N3 N4 C00G 119.88(13) . . ? C5 N4 C00G 129.43(13) . . ? C9 N1 C13 123.00(13) . . ? C9 N1 H1 118.5 . . ? C13 N1 H1 118.5 . . ? N3 N2 C6 109.35(13) . . ? N2 N3 N4 106.99(13) . . ? C00F C00C C20 116.74(14) . . ? C00F C00C C11 124.95(14) . . ? C20 C00C C11 118.31(13) . . ? N2 C6 C5 108.46(14) . . ? N2 C6 C7 119.88(14) . . ? C5 C6 C7 131.65(14) . . ? C9 C10 C16 119.50(13) . . ? C9 C10 C11 121.34(13) . . ? C16 C10 C11 118.91(13) . . ? C00R C00F C00C 121.93(15) . . ? C00R C00F CL 116.50(12) . . ? C00C C00F CL 121.57(12) . . ? C3 C00G C4 121.00(14) . . ? C3 C00G N4 119.64(14) . . ? C4 C00G N4 119.35(14) . . ? N4 C5 C6 104.50(13) . . ? N4 C5 H5 127.7 . . ? C6 C5 H5 127.7 . . ? C10 C9 N1 120.55(14) . . ? C10 C9 C8 125.04(13) . . ? N1 C9 C8 114.36(13) . . ? O5 C16 O4 121.83(14) . . ? O5 C16 C10 126.31(14) . . ? O4 C16 C10 111.85(13) . . ? C2 C3 C00G 119.20(14) . . ? C2 C3 H3 120.4 . . ? C00G C3 H3 120.4 . . ? C10 C11 C12 110.14(12) . . ? C10 C11 C00C 109.78(12) . . ? C12 C11 C00C 109.81(12) . . ? O2 C15 O3 122.42(15) . . ? O2 C15 C12 127.59(15) . . ? O3 C15 C12 109.98(13) . . ? C13 C12 C15 120.49(14) . . ? C13 C12 C11 121.98(14) . . ? C15 C12 C11 117.39(13) . . ? C00T C20 C00C 122.14(15) . . ? C00T C20 H20 118.9 . . ? C00C C20 H20 118.9 . . ? F C00P C2 119.07(14) . . ? F C00P C1 118.03(14) . . ? C2 C00P C1 122.90(15) . . ? C12 C13 N1 119.45(14) . . ? C12 C13 C14 126.89(14) . . ? N1 C13 C14 113.66(13) . . ? C00Y C00R C00F 119.82(15) . . ? C00Y C00R H00R 120.1 . . ? C00F C00R H00R 120.1 . . ? C00P C2 C3 118.93(15) . . ? C00P C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C20 C00T C00Y 119.46(16) . . ? C20 C00T H00T 120.3 . . ? C00Y C00T H00T 120.3 . . ? O1 C7 C6 107.58(13) . . ? O1 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O1 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O1 C8 C9 111.48(12) . . ? O1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? O1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 C4 C00G 119.61(15) . . ? C1 C4 H4 120.2 . . ? C00G C4 H4 120.2 . . ? C00R C00Y C00T 119.91(15) . . ? C00R C00Y H00Y 120.0 . . ? C00T C00Y H00Y 120.0 . . ? C00P C1 C4 118.35(15) . . ? C00P C1 H1A 120.8 . . ? C4 C1 H1A 120.8 . . ? O4 C17 C18 107.94(13) . . ? O4 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? O4 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? 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 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C21 C22 112.82(19) 3_565 . ? C21 C21 H21A 109.0 3_565 . ? C22 C21 H21A 109.0 . . ? C21 C21 H21B 109.0 3_565 . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 110.36(19) . . ? C21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? C21 C22 H22B 109.6 . . ? C23 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 CL C00F 1.7481(17) . ? F C00P 1.3597(18) . ? O4 C16 1.3503(19) . ? O4 C17 1.4493(18) . ? O1 C8 1.4264(18) . ? O1 C7 1.4363(19) . ? O3 C15 1.355(2) . ? O3 C19 1.4390(19) . ? O5 C16 1.2215(19) . ? O2 C15 1.215(2) . ? N4 N3 1.3581(18) . ? N4 C5 1.360(2) . ? N4 C00G 1.426(2) . ? N1 C9 1.3766(19) . ? N1 C13 1.386(2) . ? N1 H1 0.8800 . ? N2 N3 1.3074(19) . ? N2 C6 1.368(2) . ? C00C C00F 1.397(2) . ? C00C C20 1.399(2) . ? C00C C11 1.538(2) . ? C6 C5 1.369(2) . ? C6 C7 1.491(2) . ? C10 C9 1.354(2) . ? C10 C16 1.465(2) . ? C10 C11 1.529(2) . ? C00F C00R 1.393(2) . ? C00G C3 1.394(2) . ? C00G C4 1.395(2) . ? C5 H5 0.9500 . ? C9 C8 1.525(2) . ? C3 C2 1.387(2) . ? C3 H3 0.9500 . ? C11 C12 1.533(2) . ? C15 C12 1.477(2) . ? C12 C13 1.356(2) . ? C20 C00T 1.389(2) . ? C20 H20 0.9500 . ? C00P C2 1.375(2) . ? C00P C1 1.383(2) . ? C13 C14 1.506(2) . ? C00R C00Y 1.381(3) . ? C00R H00R 0.9500 . ? C2 H2 0.9500 . ? C00T C00Y 1.392(2) . ? C00T H00T 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C4 C1 1.386(2) . ? C4 H4 0.9500 . ? C00Y H00Y 0.9500 . ? C1 H1A 0.9500 . ? C17 C18 1.503(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C21 1.489(4) 3_565 ? C21 C22 1.509(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.535(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 N2 N3 N4 -0.01(19) . . . . ? C5 N4 N3 N2 -0.55(18) . . . . ? C00G N4 N3 N2 179.87(14) . . . . ? N3 N2 C6 C5 0.55(19) . . . . ? N3 N2 C6 C7 179.53(15) . . . . ? C20 C00C C00F C00R -0.3(2) . . . . ? C11 C00C C00F C00R 178.70(14) . . . . ? C20 C00C C00F CL -179.98(11) . . . . ? C11 C00C C00F CL -0.9(2) . . . . ? N3 N4 C00G C3 -169.25(15) . . . . ? C5 N4 C00G C3 11.3(2) . . . . ? N3 N4 C00G C4 10.5(2) . . . . ? C5 N4 C00G C4 -169.00(16) . . . . ? N3 N4 C5 C6 0.87(18) . . . . ? C00G N4 C5 C6 -179.61(15) . . . . ? N2 C6 C5 N4 -0.85(18) . . . . ? C7 C6 C5 N4 -179.66(17) . . . . ? C16 C10 C9 N1 179.31(14) . . . . ? C11 C10 C9 N1 -6.5(2) . . . . ? C16 C10 C9 C8 -3.4(2) . . . . ? C11 C10 C9 C8 170.73(15) . . . . ? C13 N1 C9 C10 -8.5(2) . . . . ? C13 N1 C9 C8 173.98(14) . . . . ? C17 O4 C16 O5 0.6(2) . . . . ? C17 O4 C16 C10 -178.15(14) . . . . ? C9 C10 C16 O5 3.0(3) . . . . ? C11 C10 C16 O5 -171.32(16) . . . . ? C9 C10 C16 O4 -178.36(14) . . . . ? C11 C10 C16 O4 7.3(2) . . . . ? C4 C00G C3 C2 0.5(2) . . . . ? N4 C00G C3 C2 -179.76(15) . . . . ? C9 C10 C11 C12 18.8(2) . . . . ? C16 C10 C11 C12 -166.98(14) . . . . ? C9 C10 C11 C00C -102.20(16) . . . . ? C16 C10 C11 C00C 71.99(17) . . . . ? C00F C00C C11 C10 -121.42(15) . . . . ? C20 C00C C11 C10 57.61(17) . . . . ? C00F C00C C11 C12 117.35(16) . . . . ? C20 C00C C11 C12 -63.63(17) . . . . ? C19 O3 C15 O2 -5.7(2) . . . . ? C19 O3 C15 C12 174.18(14) . . . . ? O2 C15 C12 C13 0.5(3) . . . . ? O3 C15 C12 C13 -179.45(14) . . . . ? O2 C15 C12 C11 176.25(16) . . . . ? O3 C15 C12 C11 -3.7(2) . . . . ? C10 C11 C12 C13 -19.2(2) . . . . ? C00C C11 C12 C13 101.84(17) . . . . ? C10 C11 C12 C15 165.11(13) . . . . ? C00C C11 C12 C15 -73.88(17) . . . . ? C00F C00C C20 C00T 0.4(2) . . . . ? C11 C00C C20 C00T -178.70(14) . . . . ? C15 C12 C13 N1 -177.39(14) . . . . ? C11 C12 C13 N1 7.0(2) . . . . ? C15 C12 C13 C14 2.6(3) . . . . ? C11 C12 C13 C14 -173.03(15) . . . . ? C9 N1 C13 C12 8.2(2) . . . . ? C9 N1 C13 C14 -171.75(14) . . . . ? C00C C00F C00R C00Y 0.1(2) . . . . ? CL C00F C00R C00Y 179.80(13) . . . . ? F C00P C2 C3 179.36(15) . . . . ? C1 C00P C2 C3 -0.6(3) . . . . ? C00G C3 C2 C00P 0.0(2) . . . . ? C00C C20 C00T C00Y -0.3(2) . . . . ? C8 O1 C7 C6 155.85(12) . . . . ? N2 C6 C7 O1 -64.65(19) . . . . ? C5 C6 C7 O1 114.05(19) . . . . ? C7 O1 C8 C9 -97.30(15) . . . . ? C10 C9 C8 O1 -179.98(15) . . . . ? N1 C9 C8 O1 -2.56(19) . . . . ? C3 C00G C4 C1 -0.4(3) . . . . ? N4 C00G C4 C1 179.84(16) . . . . ? C00F C00R C00Y C00T 0.0(2) . . . . ? C20 C00T C00Y C00R 0.0(2) . . . . ? F C00P C1 C4 -179.28(16) . . . . ? C2 C00P C1 C4 0.6(3) . . . . ? C00G C4 C1 C00P -0.1(3) . . . . ? C16 O4 C17 C18 175.12(14) . . . . ? C21 C21 C22 C23 -173.0(2) 3_565 . . . ?