#------------------------------------------------------------------------------ #$Date: 2021-03-30 07:51:42 +0300 (Tue, 30 Mar 2021) $ #$Revision: 263428 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022347.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2022347 loop_ _publ_author_name 'Lal Zakaria, Negin' 'Pourayoubi, Mehrdad' 'Eghbali Toularoud, Mahsa' 'Du\N-(2,6-Difluorobenzoyl)-N',N''-bis[(R)-(+)-\a-ethylbenzyl]phosphoric triamide' _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.97120(10) _cell_length_b 20.1758(2) _cell_length_c 22.7451(3) _cell_measurement_reflns_used 24203 _cell_measurement_temperature 120 _cell_measurement_theta_max 68 _cell_measurement_theta_min 4 _cell_volume 2281.29(6) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2017) ; _computing_data_collection ; GEMINI (Oxford Diffraction, 2006) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2017) ; _computing_molecular_graphics ; CAMERON (Watkin et al., 1996) ; _computing_publication_material ; CRYSTALS (Betteridge et al., 2003) ; _computing_structure_refinement ; CRYSTALS (Betteridge et al., 2003) ; _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _diffrn_ambient_temperature 120 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_unetI/netI 0.073 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 46145 _diffrn_reflns_theta_full 67.661 _diffrn_reflns_theta_max 67.661 _diffrn_reflns_theta_min 2.928 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.450 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2017) ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_description blade _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.593 _exptl_crystal_size_mid 0.126 _exptl_crystal_size_min 0.073 _refine_diff_density_max 0.19 _refine_diff_density_min -0.32 _refine_ls_abs_structure_details ; Parsons et al. (2013), 1653 Friedel Pairs ; _refine_ls_abs_structure_Flack 0.007(8) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9160 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 4088 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0299 _refine_ls_shift/su_max 0.0051084 _refine_ls_shift/su_mean 0.0007296 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.67P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0781 _refine_ls_wR_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.0781 _reflns_number_gt 3979 _reflns_number_total 4088 _reflns_threshold_expression I>2.0\s(I) _iucr_refine_instructions_details ; # # Punched on 18/03/19 at 11:56:14 # #LIST 12 BLOCK CONT SCALE CONT P ( 1 ,X'S,U'S) UNTIL C ( 33 ) CONT H ( 31 ,X'S,U[ISO]) UNTIL H ( 241 ) CONT ENANTIO RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 222,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 233,X'S) H ( 232,X'S) H ( 231,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 28,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) H ( 322,X'S) RIDE C ( 33,X'S) H ( 332,X'S) H ( 331,X'S) H ( 333,X'S) END # # Punched on 18/03/19 at 11:56:14 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM NO H NO #H U MULT DIST REM C-H REM >4 1.5 .96 DISORDER REM 1 1 1.2 .93 C C-H (ACETYLENE) REM 1 2 1.2 .93 C-C(H)-C REM 1 3 1.2 .98 (C)3-C-H REM 2 1 1.2 .93 C=C-H(2) REM 2 2 1.2 .97 (C)2-C-(H)2 REM 3 1 1.5 .96 C-C-(H)3 REM N-H REM >4 1.5 .89 DISORDER REM 1 1 1.2 .86 N-N/H REM 1 2 1.2 .86 (C)2-N-H REM 1 3 1.2 .89 (C)3-N-H REM 2 1 1.2 .86 C-N-(H)2 REM 2 2 1.2 .89 (C)2-N-(H)2 REM 3 1 1.2 .89 C-H-(H)3 REM O-H REM 1 1 1.5 .82 O-H REM REM DIST ESD = 0.02 REM VIB ESD = 0.002 REM ANGLE ESD = 2.0 REM REM TO ACTIVATE THE VIB RESTRAINTS, REMOVE LEADING REM REM H1-N-R2 DIST 0.86, 0.02 = CONT N ( 3) TO H(31) REST 0.022, 0.002 = H(31,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(31) TO N ( 3) TO P(1) CONT H(31) TO N ( 3) TO C(4) REM H1-N-R2 DIST 0.86, 0.02 = CONT N ( 14) TO H(141) REST 0.022, 0.002 = H(141,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(141) TO N ( 14) TO P(1) CONT H(141) TO N ( 14) TO C(15) REM H1-N-R2 DIST 0.86, 0.02 = CONT N ( 24) TO H(241) REST 0.021, 0.002 = H(241,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(241) TO N ( 24) TO P(1) CONT H(241) TO N ( 24) TO C(25) REM HREST END (DO NOT REMOVE THIS LINE) END ; _cod_data_source_file fp3087sup1.cif _cod_data_source_block III _cod_original_sg_symbol_H-M 'P 21 21 21 ' _cod_original_formula_sum 'C25 H28 F2 N3 O2 P1' _cod_database_code 2022347 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_site_type_symbol _atom_site_label _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_disorder_assembly _atom_site_disorder_group P P1 0.07561(10) 0.66910(2) 0.73635(2) 0.0154 Uani 1.0000 . . O O2 -0.1943(3) 0.64055(6) 0.74758(6) 0.0193 Uani 1.0000 . . N N3 0.0035(3) 0.74731(8) 0.71194(8) 0.0184 Uani 1.0000 . . C C4 0.1933(4) 0.79514(9) 0.70452(8) 0.0176 Uani 1.0000 . . O O5 0.4344(3) 0.78367(7) 0.70908(6) 0.0223 Uani 1.0000 . . C C6 0.0926(4) 0.86420(9) 0.69282(8) 0.0189 Uani 1.0000 . . C C7 -0.1059(4) 0.87973(10) 0.65208(9) 0.0226 Uani 1.0000 . . C C8 -0.1952(5) 0.94327(11) 0.64216(10) 0.0291 Uani 1.0000 . . C C9 -0.0815(5) 0.99459(10) 0.67407(10) 0.0310 Uani 1.0000 . . C C10 0.1194(5) 0.98211(10) 0.71476(10) 0.0300 Uani 1.0000 . . C C11 0.2004(5) 0.91766(10) 0.72311(9) 0.0245 Uani 1.0000 . . F F12 0.3887(3) 0.90571(6) 0.76440(6) 0.0369 Uani 1.0000 . . F F13 -0.2090(3) 0.83004(6) 0.61943(5) 0.0283 Uani 1.0000 . . N N14 0.2733(3) 0.67199(8) 0.79303(7) 0.0184 Uani 1.0000 . . C C15 0.1893(4) 0.69598(10) 0.85128(8) 0.0191 Uani 1.0000 . . C C16 0.3211(4) 0.65541(10) 0.90037(9) 0.0211 Uani 1.0000 . . C C17 0.5328(4) 0.61208(10) 0.89036(9) 0.0228 Uani 1.0000 . . C C18 0.6495(5) 0.57716(11) 0.93681(10) 0.0297 Uani 1.0000 . . C C19 0.5563(6) 0.58553(12) 0.99347(9) 0.0338 Uani 1.0000 . . C C20 0.3440(6) 0.62834(13) 1.00383(10) 0.0372 Uani 1.0000 . . C C21 0.2288(5) 0.66332(11) 0.95787(9) 0.0299 Uani 1.0000 . . C C22 0.2386(4) 0.77051(10) 0.85989(9) 0.0234 Uani 1.0000 . . C C23 0.5339(5) 0.78974(10) 0.85830(10) 0.0280 Uani 1.0000 . . N N24 0.2604(3) 0.63258(8) 0.68762(7) 0.0178 Uani 1.0000 . . C C25 0.1588(4) 0.61409(10) 0.62893(8) 0.0194 Uani 1.0000 . . C C26 0.3720(4) 0.62699(10) 0.58186(8) 0.0206 Uani 1.0000 . . C C27 0.5128(4) 0.68640(10) 0.58219(9) 0.0230 Uani 1.0000 . . C C28 0.6998(5) 0.70132(11) 0.53869(9) 0.0265 Uani 1.0000 . . C C29 0.7507(5) 0.65638(11) 0.49428(9) 0.0274 Uani 1.0000 . . C C30 0.6115(5) 0.59720(11) 0.49313(9) 0.0306 Uani 1.0000 . . C C31 0.4222(5) 0.58281(10) 0.53591(9) 0.0266 Uani 1.0000 . . C C32 0.0389(4) 0.54377(10) 0.62948(9) 0.0248 Uani 1.0000 . . C C33 0.2337(5) 0.48950(10) 0.64869(10) 0.0327 Uani 1.0000 . . H H81 -0.3287 0.9503 0.6140 0.0359 Uiso 1.0000 . . H H91 -0.1395 1.0394 0.6668 0.0376 Uiso 1.0000 . . H H101 0.1991 1.0169 0.7367 0.0367 Uiso 1.0000 . . H H151 -0.0057 0.6873 0.8547 0.0227 Uiso 1.0000 . . H H171 0.5954 0.6063 0.8518 0.0273 Uiso 1.0000 . . H H181 0.7955 0.5491 0.9300 0.0370 Uiso 1.0000 . . H H191 0.6370 0.5615 1.0247 0.0407 Uiso 1.0000 . . H H201 0.2794 0.6344 1.0419 0.0438 Uiso 1.0000 . . H H211 0.0858 0.6934 0.9662 0.0375 Uiso 1.0000 . . H H222 0.1610 0.7842 0.8978 0.0284 Uiso 1.0000 . . H H221 0.1473 0.7943 0.8294 0.0278 Uiso 1.0000 . . H H233 0.5494 0.8373 0.8629 0.0422 Uiso 1.0000 . . H H232 0.6311 0.7676 0.8893 0.0428 Uiso 1.0000 . . H H231 0.6152 0.7772 0.8207 0.0417 Uiso 1.0000 . . H H251 0.0063 0.6449 0.6219 0.0236 Uiso 1.0000 . . H H271 0.4795 0.7170 0.6122 0.0283 Uiso 1.0000 . . H H281 0.7928 0.7419 0.5402 0.0326 Uiso 1.0000 . . H H291 0.8843 0.6664 0.4649 0.0346 Uiso 1.0000 . . H H301 0.6427 0.5663 0.4631 0.0370 Uiso 1.0000 . . H H311 0.3221 0.5426 0.5339 0.0318 Uiso 1.0000 . . H H321 -0.1156 0.5460 0.6567 0.0292 Uiso 1.0000 . . H H322 -0.0366 0.5322 0.5913 0.0302 Uiso 1.0000 . . H H332 0.1515 0.4464 0.6501 0.0491 Uiso 1.0000 . . H H331 0.2988 0.5003 0.6875 0.0479 Uiso 1.0000 . . H H333 0.3906 0.4866 0.6221 0.0488 Uiso 1.0000 . . H H31 -0.163(3) 0.7587(8) 0.7110(10) 0.0220(19) Uiso 1.0000 . . H H141 0.439(3) 0.6737(11) 0.7864(7) 0.0229(19) Uiso 1.0000 . . H H241 0.428(3) 0.6274(11) 0.6939(7) 0.0225(19) Uiso 1.0000 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0122(2) 0.0150(2) 0.0190(2) 0.00001(19) 0.00033(19) -0.00053(18) O2 0.0125(6) 0.0190(6) 0.0264(7) -0.0011(5) 0.0004(5) 0.0010(5) N3 0.0103(8) 0.0174(8) 0.0277(8) 0.0007(6) -0.0002(6) 0.0010(7) C4 0.0169(10) 0.0186(9) 0.0174(9) -0.0008(8) 0.0009(8) -0.0013(7) O5 0.0121(7) 0.0217(7) 0.0332(7) 0.0005(6) 0.0006(6) 0.0012(6) C6 0.0166(9) 0.0190(9) 0.0212(9) 0.0013(8) 0.0027(8) 0.0006(7) C7 0.0199(10) 0.0231(10) 0.0247(10) -0.0015(8) 0.0022(8) 0.0020(8) C8 0.0245(11) 0.0312(11) 0.0316(11) 0.0049(9) -0.0004(10) 0.0096(9) C9 0.0353(13) 0.0191(10) 0.0385(12) 0.0085(10) 0.0094(11) 0.0051(9) C10 0.0387(14) 0.0188(10) 0.0324(11) -0.0016(9) 0.0043(10) -0.0020(8) C11 0.0266(11) 0.0222(10) 0.0247(10) -0.0013(9) -0.0003(9) 0.0019(8) F12 0.0419(8) 0.0255(6) 0.0432(7) -0.0050(6) -0.0210(7) -0.0020(5) F13 0.0285(6) 0.0281(6) 0.0284(6) -0.0046(6) -0.0083(5) 0.0023(5) N14 0.0115(8) 0.0231(8) 0.0205(8) -0.0001(7) 0.0010(6) -0.0029(7) C15 0.0125(9) 0.0255(10) 0.0194(9) 0.0005(8) 0.0010(8) -0.0044(8) C16 0.0208(10) 0.0213(10) 0.0211(10) -0.0061(8) -0.0003(8) -0.0011(7) C17 0.0230(11) 0.0250(10) 0.0205(10) -0.0022(8) 0.0021(8) 0.0007(8) C18 0.0307(13) 0.0265(11) 0.0318(11) -0.0008(9) -0.0013(9) 0.0058(9) C19 0.0424(15) 0.0338(12) 0.0252(11) -0.0056(11) -0.0056(11) 0.0073(9) C20 0.0481(17) 0.0428(14) 0.0209(11) -0.0061(12) 0.0047(10) 0.0016(9) C21 0.0306(12) 0.0345(11) 0.0245(10) 0.0011(10) 0.0046(9) -0.0042(9) C22 0.0216(11) 0.0231(10) 0.0255(10) 0.0016(9) -0.0010(9) -0.0047(8) C23 0.0264(12) 0.0230(10) 0.0345(11) -0.0030(9) -0.0062(10) -0.0028(9) N24 0.0110(8) 0.0228(8) 0.0196(8) 0.0011(7) -0.0008(6) -0.0019(6) C25 0.0158(10) 0.0225(10) 0.0200(9) 0.0028(8) -0.0039(8) -0.0022(7) C26 0.0201(11) 0.0234(10) 0.0183(9) 0.0040(8) -0.0035(8) 0.0018(7) C27 0.0227(11) 0.0251(10) 0.0211(10) 0.0020(8) 0.0007(8) -0.0005(8) C28 0.0245(11) 0.0306(11) 0.0245(10) -0.0009(9) -0.0009(9) 0.0034(8) C29 0.0251(12) 0.0353(12) 0.0217(10) 0.0049(9) 0.0019(9) 0.0046(8) C30 0.0386(14) 0.0326(12) 0.0208(10) 0.0085(10) 0.0034(10) -0.0032(8) C31 0.0315(12) 0.0241(10) 0.0242(10) 0.0013(10) -0.0008(10) -0.0023(8) C32 0.0240(11) 0.0255(11) 0.0249(10) -0.0023(9) -0.0023(9) -0.0036(8) C33 0.0412(14) 0.0227(11) 0.0342(12) 0.0002(10) 0.0036(11) 0.0013(9) loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 2.3100 1.0200 1.5886 0.8650 20.8439 10.2075 0.5687 51.6512 0.2156 0.0181 0.0091 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.4930 0.3229 0.1402 0.0408 10.5109 26.1257 3.1424 57.7998 0.0030 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 3.0485 2.2868 1.5463 0.8670 13.2771 5.7011 0.3239 32.9089 0.2508 0.0492 0.0322 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 6.4345 4.1791 1.7800 1.4908 1.9067 27.1570 0.5260 68.1645 1.1149 0.2955 0.4335 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 3.5392 2.6412 1.5170 1.0243 10.2825 4.2944 0.2615 26.1476 0.2776 0.0727 0.0534 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 12.2126 3.1322 2.0125 1.1663 0.0057 9.8933 28.9975 0.5826 -11.5290 0.0311 0.0180 'International Tables Vol C 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 P1 N3 . . . 102.99(8) yes O2 P1 N14 . . . 115.18(8) yes N3 P1 N14 . . . 110.60(9) yes O2 P1 N24 . . . 117.08(8) yes N3 P1 N24 . . . 108.47(8) yes N14 P1 N24 . . . 102.52(8) yes P1 N3 C4 . . . 123.32(14) yes P1 N3 H31 . . . 117.1(11) no C4 N3 H31 . . . 118.4(11) no N3 C4 O5 . . . 122.30(18) no N3 C4 C6 . . . 116.62(17) no O5 C4 C6 . . . 121.04(17) no C4 C6 C7 . . . 124.28(17) no C4 C6 C11 . . . 120.24(18) no C7 C6 C11 . . . 115.48(18) no C6 C7 C8 . . . 123.28(19) no C6 C7 F13 . . . 118.01(17) no C8 C7 F13 . . . 118.67(19) no C7 C8 C9 . . . 118.6(2) no C7 C8 H81 . . . 119.0 no C9 C8 H81 . . . 122.4 no C8 C9 C10 . . . 120.58(19) no C8 C9 H91 . . . 119.3 no C10 C9 H91 . . . 120.1 no C9 C10 C11 . . . 118.4(2) no C9 C10 H101 . . . 121.2 no C11 C10 H101 . . . 120.4 no C6 C11 C10 . . . 123.6(2) no C6 C11 F12 . . . 118.37(18) no C10 C11 F12 . . . 117.96(19) no P1 N14 C15 . . . 123.74(13) yes P1 N14 H141 . . . 117.0(11) no C15 N14 H141 . . . 115.3(11) no N14 C15 C16 . . . 111.04(16) no N14 C15 C22 . . . 113.06(16) no C16 C15 C22 . . . 111.22(16) no N14 C15 H151 . . . 107.0 no C16 C15 H151 . . . 105.5 no C22 C15 H151 . . . 108.6 no C15 C16 C17 . . . 122.81(17) no C15 C16 C21 . . . 118.77(19) no C17 C16 C21 . . . 118.40(19) no C16 C17 C18 . . . 120.60(19) no C16 C17 H171 . . . 119.0 no C18 C17 H171 . . . 120.4 no C17 C18 C19 . . . 120.4(2) no C17 C18 H181 . . . 120.3 no C19 C18 H181 . . . 119.3 no C18 C19 C20 . . . 119.4(2) no C18 C19 H191 . . . 119.6 no C20 C19 H191 . . . 120.9 no C19 C20 C21 . . . 120.3(2) no C19 C20 H201 . . . 120.2 no C21 C20 H201 . . . 119.4 no C16 C21 C20 . . . 120.9(2) no C16 C21 H211 . . . 120.3 no C20 C21 H211 . . . 118.8 no C15 C22 C23 . . . 113.66(17) no C15 C22 H222 . . . 108.9 no C23 C22 H222 . . . 109.2 no C15 C22 H221 . . . 108.8 no C23 C22 H221 . . . 108.2 no H222 C22 H221 . . . 108.0 no C22 C23 H233 . . . 109.1 no C22 C23 H232 . . . 110.4 no H233 C23 H232 . . . 109.8 no C22 C23 H231 . . . 110.7 no H233 C23 H231 . . . 108.6 no H232 C23 H231 . . . 108.2 no P1 N24 C25 . . . 122.74(13) no P1 N24 H241 . . . 119.9(11) no C25 N24 H241 . . . 117.0(11) no N24 C25 C26 . . . 110.68(15) no N24 C25 C32 . . . 111.00(16) no C26 C25 C32 . . . 115.55(16) no N24 C25 H251 . . . 104.4 no C26 C25 H251 . . . 108.1 no C32 C25 H251 . . . 106.4 no C25 C26 C27 . . . 119.53(17) no C25 C26 C31 . . . 122.65(18) no C27 C26 C31 . . . 117.72(19) no C26 C27 C28 . . . 121.35(19) no C26 C27 H271 . . . 119.0 no C28 C27 H271 . . . 119.7 no C27 C28 C29 . . . 120.1(2) no C27 C28 H281 . . . 119.4 no C29 C28 H281 . . . 120.5 no C28 C29 C30 . . . 119.3(2) no C28 C29 H291 . . . 119.7 no C30 C29 H291 . . . 120.9 no C29 C30 C31 . . . 120.6(2) no C29 C30 H301 . . . 120.4 no C31 C30 H301 . . . 119.0 no C26 C31 C30 . . . 120.9(2) no C26 C31 H311 . . . 119.0 no C30 C31 H311 . . . 120.0 no C25 C32 C33 . . . 114.71(18) no C25 C32 H321 . . . 105.3 no C33 C32 H321 . . . 110.3 no C25 C32 H322 . . . 111.3 no C33 C32 H322 . . . 109.1 no H321 C32 H322 . . . 105.7 no C32 C33 H332 . . . 112.9 no C32 C33 H331 . . . 108.2 no H332 C33 H331 . . . 108.4 no C32 C33 H333 . . . 111.6 no H332 C33 H333 . . . 107.5 no H331 C33 H333 . . . 108.0 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O2 . . 1.4823(14) yes P1 N3 . . 1.7107(16) yes P1 N14 . . 1.6221(16) yes P1 N24 . . 1.6173(16) yes N3 C4 . . 1.360(3) yes N3 H31 . . 0.861(16) no C4 O5 . . 1.225(3) yes C4 C6 . . 1.504(3) no C6 C7 . . 1.389(3) no C6 C11 . . 1.387(3) yes C7 C8 . . 1.375(3) yes C7 F13 . . 1.349(2) yes C8 C9 . . 1.385(3) yes C8 H81 . . 0.933 no C9 C10 . . 1.385(3) no C9 H91 . . 0.962 no C10 C11 . . 1.375(3) no C10 H101 . . 0.948 no C11 F12 . . 1.348(3) no N14 C15 . . 1.471(2) yes N14 H141 . . 0.836(16) no C15 C16 . . 1.532(3) no C15 C22 . . 1.536(3) no C15 H151 . . 0.988 no C16 C17 . . 1.387(3) no C16 C21 . . 1.395(3) no C17 C18 . . 1.396(3) no C17 H171 . . 0.938 no C18 C19 . . 1.380(3) no C18 H181 . . 0.933 no C19 C20 . . 1.384(4) no C19 H191 . . 0.948 no C20 C21 . . 1.385(3) no C20 H201 . . 0.932 no C21 H211 . . 0.954 no C22 C23 . . 1.519(3) no C22 H222 . . 0.984 no C22 H221 . . 0.958 no C23 H233 . . 0.969 no C23 H232 . . 0.965 no C23 H231 . . 0.979 no N24 C25 . . 1.475(2) yes N24 H241 . . 0.849(16) no C25 C26 . . 1.529(3) no C25 C32 . . 1.539(3) no C25 H251 . . 0.993 no C26 C27 . . 1.388(3) no C26 C31 . . 1.396(3) no C27 C28 . . 1.390(3) no C27 H271 . . 0.936 no C28 C29 . . 1.381(3) no C28 H281 . . 0.940 no C29 C30 . . 1.380(3) no C29 H291 . . 0.963 no C30 C31 . . 1.384(3) no C30 H301 . . 0.936 no C31 H311 . . 0.953 no C32 C33 . . 1.526(3) no C32 H321 . . 0.988 no C32 H322 . . 0.974 no C33 H332 . . 0.962 no C33 H331 . . 0.965 no C33 H333 . . 0.989 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C10 H101 O2 . . 3_556 0.95 2.52 3.330(3) 144 yes C27 H271 O5 . . . 0.94 2.59 3.512(3) 168 yes N3 H31 O5 . . 1_455 0.861 2.063 2.923(3) 178.6(15) yes N14 H141 O2 . . 1_655 0.836 2.135 2.911(3) 154.4(18) yes N24 H241 O2 . . 1_655 0.849 2.258 3.039(3) 152.9(14) yes C28 H281 F13 . . 1_655 0.94 2.53 3.213(2) 129.45(13) yes C17 H171 O2 . . 1_655 0.94 2.68 3.566(2) 157.52(13) yes _cod_database_fobs_code 2022347