#------------------------------------------------------------------------------ #$Date: 2025-05-24 03:04:39 +0300 (Sat, 24 May 2025) $ #$Revision: 299803 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/25/04/7250443.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_7250443 loop_ _publ_author_name 'Kwain, Samuel' 'Morris, James W. D.' 'McKeon, Jillian Elisa Milanes' 'Roster, Colm P.' 'Noori, Monireh' 'Gibbs, Aysiah R.' 'Stevenson III, Robert L' 'McMillen, Colin' 'Dominy, Brian N.' 'Morris, James C.' 'Whitehead, Daniel Charles' _publ_section_title ; Assessment of the structure-activity relationship of analogs of the Naegleria fowleri enolase inhibitor HEX ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D5MD00277J _journal_year 2025 _chemical_absolute_configuration ad _chemical_formula_sum 'C5 H13 N2 O5 P' _chemical_formula_weight 212.14 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2025-03-27 deposited with the CCDC. 2025-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.1084(3) _cell_length_b 8.9906(5) _cell_length_c 15.9200(9) _cell_measurement_reflns_used 9959 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.88 _cell_measurement_theta_min 3.42 _cell_volume 874.30(8) _computing_cell_refinement 'SAINT v8.37a (Bruker, 2016)' _computing_data_collection 'APEX3 v2017.3 (Bruker, 2017)' _computing_data_reduction 'SAINT v8.37a (Bruker, 2016)' _computing_molecular_graphics 'Mercury 2021.3.0 (Macrae et al. 2020)' _computing_publication_material 'PublCIF v1.9.21_c (Westrip, 2010)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2015a)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Quest Photon 3' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_unetI/netI 0.0249 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 48153 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.944 _diffrn_reflns_theta_min 3.418 _diffrn_source 'Incoatec I\mS' _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/5 (Krause et al., 2015)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.612 _exptl_crystal_description needle _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.403 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.064 _refine_ls_abs_structure_details ; Flack x determined using 799 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.05(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 142 _refine_ls_number_reflns 2086 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0314 _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^)+(0.0472P)^2^+0.1429P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.0787 _reflns_Friedel_coverage 0.695 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 1995 _reflns_number_total 2086 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5md00277j2.cif _cod_data_source_block 1 _cod_database_code 7250443 _shelx_shelxl_version_number 2016/6 _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 0.913 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL q-2137_a.res in P2(1)2(1)2(1) q-2137_a.res created by SHELXL-2016/6 at 11:12:59 on 09-Oct-2024 REM Old TITL q-2137 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.089, Rweak 0.018, Alpha 0.003, Orientation as input REM Flack x = -0.021 ( 0.039 ) from Parsons' quotients REM Formula found by SHELXT: C6 N O5 P CELL 0.71073 6.1084 8.9906 15.9200 90.000 90.000 90.000 ZERR 4.000 0.0003 0.0005 0.0009 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O P UNIT 20 52 8 20 4 TEMP -123.150 SIZE 0.03 0.08 0.30 L.S. 10 BOND $H LIST 4 ACTA CONF HTAB O3 O5W EQIV $1 x+1/2, -y+3/2, -z+1 HTAB N2 O1_$1 HTAB N2 O3_$1 EQIV $2 -x+3/2, -y+1, z-1/2 HTAB N2 O4_$2 HTAB N2 O1 EQIV $3 x-1/2, -y+3/2, -z+1 HTAB N2 O2_$3 EQIV $4 -x+1, y-1/2, -z+3/2 HTAB C4 O5W_$4 HTAB C5 O5W_$2 HTAB O5W O2_$4 EQIV $5 x-1, y, z HTAB O5W O4_$5 FMAP 2 PLAN 20 omit 0 1 1 omit 1 1 0 omit 0 0 2 omit 1 0 1 WGHT 0.047200 0.142900 FVAR 1.02447 P1 5 0.698350 0.681456 0.707425 11.00000 0.01108 0.01340 = 0.01006 0.00009 0.00063 0.00047 O1 4 0.475437 0.658575 0.534297 11.00000 0.01976 0.03031 = 0.01293 -0.00261 -0.00266 0.00844 O2 4 0.825583 0.807548 0.669671 11.00000 0.01813 0.01614 = 0.01905 0.00064 0.00474 -0.00306 O3 4 0.453410 0.731854 0.715657 11.00000 0.01251 0.02319 = 0.01440 0.00344 0.00210 0.00338 H3O 2 0.379762 0.676873 0.752437 11.00000 0.06738 O4 4 0.779118 0.621814 0.790119 11.00000 0.01477 0.01898 = 0.01149 0.00004 -0.00083 0.00159 N1 3 0.762582 0.537327 0.479986 11.00000 0.01489 0.01986 = 0.00898 0.00254 -0.00053 0.00079 N2 3 0.712315 0.604843 0.401469 11.00000 0.01310 0.01765 = 0.00890 0.00200 -0.00039 -0.00100 H2N1 2 0.809232 0.680966 0.395481 11.00000 0.01357 H2N2 2 0.725544 0.550019 0.355774 11.00000 0.02705 H2N3 2 0.585503 0.633764 0.405265 11.00000 0.02506 C1 1 0.639611 0.581563 0.545849 11.00000 0.01672 0.01379 = 0.01220 -0.00123 -0.00130 -0.00252 C2 1 0.710185 0.527482 0.632105 11.00000 0.01789 0.01447 = 0.00989 -0.00008 0.00082 0.00209 AFIX 13 H2 2 0.603700 0.449738 0.650776 11.00000 -1.20000 AFIX 0 C3 1 0.940665 0.459568 0.635552 11.00000 0.02532 0.02224 = 0.01375 -0.00109 -0.00435 0.01027 AFIX 23 H3A 2 1.050299 0.540456 0.638848 11.00000 -1.20000 H3B 2 0.954573 0.398141 0.686886 11.00000 -1.20000 AFIX 0 C4 1 0.987953 0.363745 0.558890 11.00000 0.02939 0.02103 = 0.01678 -0.00038 -0.00067 0.01023 AFIX 23 H4A 2 1.136248 0.320051 0.563433 11.00000 -1.20000 H4B 2 0.880558 0.281483 0.555588 11.00000 -1.20000 AFIX 0 C5 1 0.973100 0.458952 0.480886 11.00000 0.01770 0.02416 = 0.01347 0.00035 0.00055 0.00730 AFIX 23 H5A 2 1.094504 0.531892 0.480264 11.00000 -1.20000 H5B 2 0.986050 0.395619 0.430258 11.00000 -1.20000 AFIX 0 O5W 4 0.212672 0.600045 0.819117 11.00000 0.01312 0.01992 = 0.02387 0.00294 -0.00034 0.00058 H5C 2 0.219251 0.501565 0.824323 11.00000 0.03670 H5D 2 0.086465 0.615848 0.804873 11.00000 0.02998 HKLF 4 REM q-2137_a.res in P2(1)2(1)2(1) REM R1 = 0.0314 for 1995 Fo > 4sig(Fo) and 0.0331 for all 2086 data REM 142 parameters refined using 0 restraints END WGHT 0.0472 0.1429 REM Highest difference peak 0.403, deepest hole -0.208, 1-sigma level 0.064 Q1 1 0.7162 0.6292 0.7539 11.00000 0.05 0.40 Q2 1 0.7071 0.6084 0.6640 11.00000 0.05 0.38 Q3 1 0.7439 0.6658 0.8137 11.00000 0.05 0.28 Q4 1 0.7240 0.7795 0.6842 11.00000 0.05 0.28 Q5 1 0.7991 0.7467 0.6932 11.00000 0.05 0.27 Q6 1 0.7489 0.5700 0.4461 11.00000 0.05 0.26 Q7 1 0.9583 0.4136 0.5202 11.00000 0.05 0.26 Q8 1 0.5636 0.7194 0.7079 11.00000 0.05 0.26 Q9 1 0.8499 0.4995 0.4797 11.00000 0.05 0.23 Q10 1 0.9809 0.4125 0.5969 11.00000 0.05 0.23 Q11 1 0.6777 0.5268 0.4996 11.00000 0.05 0.22 Q12 1 0.4969 0.5894 0.5280 11.00000 0.05 0.22 Q13 1 0.6776 0.5459 0.5876 11.00000 0.05 0.21 Q14 1 0.1870 0.6508 0.8615 11.00000 0.05 0.20 Q15 1 0.2888 0.6308 0.7845 11.00000 0.05 0.20 Q16 1 0.7467 0.5839 0.5114 11.00000 0.05 0.20 Q17 1 0.8163 0.4943 0.6292 11.00000 0.05 0.20 Q18 1 0.5377 0.6639 0.5429 11.00000 0.05 0.19 Q19 1 1.0256 0.4577 0.5862 11.00000 0.05 0.19 Q20 1 0.9256 0.7783 0.6582 11.00000 0.05 0.18 ; _shelx_res_checksum 27340 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 P1 P 0.69835(9) 0.68146(6) 0.70742(4) 0.01151(16) Uani 1 1 d . . . . . O1 O 0.4754(3) 0.6586(2) 0.53430(11) 0.0210(4) Uani 1 1 d . . . . . O2 O 0.8256(3) 0.80755(18) 0.66967(10) 0.0178(4) Uani 1 1 d . . . . . O3 O 0.4534(3) 0.7319(2) 0.71566(11) 0.0167(4) Uani 1 1 d . . . . . H3O H 0.380(8) 0.677(5) 0.752(3) 0.067(14) Uiso 1 1 d . . . . . O4 O 0.7791(3) 0.62181(17) 0.79012(10) 0.0151(3) Uani 1 1 d . . . . . N1 N 0.7626(3) 0.5373(2) 0.47999(12) 0.0146(4) Uani 1 1 d . . . . . N2 N 0.7123(4) 0.6048(2) 0.40147(12) 0.0132(4) Uani 1 1 d . . . . . H2N1 H 0.809(5) 0.681(3) 0.3955(18) 0.014(6) Uiso 1 1 d . . . . . H2N2 H 0.726(6) 0.550(4) 0.356(2) 0.027(8) Uiso 1 1 d . . . . . H2N3 H 0.586(6) 0.634(4) 0.405(2) 0.025(8) Uiso 1 1 d . . . . . C1 C 0.6396(4) 0.5816(2) 0.54585(14) 0.0142(5) Uani 1 1 d . . . . . C2 C 0.7102(4) 0.5275(2) 0.63211(13) 0.0141(4) Uani 1 1 d . . . . . H2 H 0.603700 0.449738 0.650776 0.017 Uiso 1 1 calc R U . . . C3 C 0.9407(4) 0.4596(3) 0.63555(15) 0.0204(5) Uani 1 1 d . . . . . H3A H 1.050299 0.540456 0.638848 0.025 Uiso 1 1 calc R U . . . H3B H 0.954573 0.398141 0.686886 0.025 Uiso 1 1 calc R U . . . C4 C 0.9880(5) 0.3637(3) 0.55889(15) 0.0224(6) Uani 1 1 d . . . . . H4A H 1.136248 0.320051 0.563433 0.027 Uiso 1 1 calc R U . . . H4B H 0.880558 0.281483 0.555588 0.027 Uiso 1 1 calc R U . . . C5 C 0.9731(4) 0.4590(3) 0.48089(15) 0.0184(5) Uani 1 1 d . . . . . H5A H 1.094504 0.531892 0.480264 0.022 Uiso 1 1 calc R U . . . H5B H 0.986050 0.395619 0.430258 0.022 Uiso 1 1 calc R U . . . O5W O 0.2127(3) 0.6000(2) 0.81912(11) 0.0190(4) Uani 1 1 d . . . . . H5C H 0.219(6) 0.502(4) 0.824(2) 0.037(10) Uiso 1 1 d . . . . . H5D H 0.086(6) 0.616(4) 0.805(2) 0.030(9) Uiso 1 1 d . . . . . 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 P1 0.0111(3) 0.0134(3) 0.0101(3) 0.0001(2) 0.0006(2) 0.0005(2) O1 0.0198(9) 0.0303(10) 0.0129(8) -0.0026(7) -0.0027(7) 0.0084(8) O2 0.0181(8) 0.0161(7) 0.0191(8) 0.0006(6) 0.0047(7) -0.0031(7) O3 0.0125(8) 0.0232(8) 0.0144(8) 0.0034(7) 0.0021(7) 0.0034(7) O4 0.0148(8) 0.0190(7) 0.0115(7) 0.0000(6) -0.0008(7) 0.0016(6) N1 0.0149(10) 0.0199(9) 0.0090(9) 0.0025(7) -0.0005(7) 0.0008(8) N2 0.0131(10) 0.0177(9) 0.0089(9) 0.0020(7) -0.0004(8) -0.0010(9) C1 0.0167(11) 0.0138(10) 0.0122(11) -0.0012(8) -0.0013(8) -0.0025(9) C2 0.0179(11) 0.0145(10) 0.0099(10) -0.0001(8) 0.0008(9) 0.0021(9) C3 0.0253(13) 0.0222(12) 0.0137(11) -0.0011(9) -0.0043(10) 0.0103(10) C4 0.0294(14) 0.0210(12) 0.0168(12) -0.0004(10) -0.0007(10) 0.0102(10) C5 0.0177(12) 0.0242(13) 0.0135(11) 0.0004(9) 0.0005(9) 0.0073(10) O5W 0.0131(8) 0.0199(9) 0.0239(9) 0.0029(7) -0.0003(7) 0.0006(7) 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' P P 0.1023 0.0942 '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 O2 P1 O4 116.74(10) . . ? O2 P1 O3 108.02(10) . . ? O4 P1 O3 110.03(10) . . ? O2 P1 C2 106.75(10) . . ? O4 P1 C2 106.88(10) . . ? O3 P1 C2 108.08(11) . . ? P1 O3 H3O 112(3) . . ? C1 N1 N2 115.89(18) . . ? C1 N1 C5 128.5(2) . . ? N2 N1 C5 113.75(18) . . ? N1 N2 H2N1 105.8(18) . . ? N1 N2 H2N2 118(2) . . ? H2N1 N2 H2N2 106(3) . . ? N1 N2 H2N3 106(2) . . ? H2N1 N2 H2N3 113(3) . . ? H2N2 N2 H2N3 109(3) . . ? O1 C1 N1 120.2(2) . . ? O1 C1 C2 123.1(2) . . ? N1 C1 C2 116.7(2) . . ? C1 C2 C3 114.82(19) . . ? C1 C2 P1 109.78(15) . . ? C3 C2 P1 108.25(16) . . ? C1 C2 H2 107.9 . . ? C3 C2 H2 107.9 . . ? P1 C2 H2 107.9 . . ? C4 C3 C2 111.7(2) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 109.1(2) . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N1 C5 C4 109.4(2) . . ? N1 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? N1 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? H5C O5W H5D 104(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 P1 O2 1.5001(17) . ? P1 O4 1.5047(17) . ? P1 O3 1.5688(17) . ? P1 C2 1.833(2) . ? O1 C1 1.232(3) . ? O3 H3O 0.89(5) . ? N1 C1 1.350(3) . ? N1 N2 1.423(3) . ? N1 C5 1.466(3) . ? N2 H2N1 0.91(3) . ? N2 H2N2 0.88(3) . ? N2 H2N3 0.82(4) . ? C1 C2 1.519(3) . ? C2 C3 1.536(3) . ? C2 H2 1.0000 . ? C3 C4 1.522(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.511(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? O5W H5C 0.89(4) . ? O5W H5D 0.82(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 O3 H3O O5W 0.89(5) 1.63(5) 2.506(2) 170(5) . N2 H2N1 O1 0.91(3) 2.09(3) 2.855(3) 141(2) 4_566 N2 H2N1 O3 0.91(3) 2.13(3) 2.793(3) 129(2) 4_566 N2 H2N2 O4 0.88(3) 1.87(3) 2.701(3) 157(3) 2_664 N2 H2N3 O1 0.82(4) 2.17(4) 2.607(3) 113(3) . N2 H2N3 O2 0.82(4) 2.05(4) 2.736(3) 140(3) 4_466 C4 H4B O5W 0.99 2.64 3.301(3) 124.4 3_646 C5 H5B O5W 0.99 2.55 3.255(3) 127.8 2_664 O5W H5C O2 0.89(4) 1.77(4) 2.646(2) 168(4) 3_646 O5W H5D O4 0.82(4) 1.89(4) 2.695(3) 168(3) 1_455 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 N2 N1 C1 O1 10.2(3) . . . . ? C5 N1 C1 O1 173.4(2) . . . . ? N2 N1 C1 C2 -171.81(19) . . . . ? C5 N1 C1 C2 -8.6(3) . . . . ? O1 C1 C2 C3 -168.6(2) . . . . ? N1 C1 C2 C3 13.4(3) . . . . ? O1 C1 C2 P1 -46.4(3) . . . . ? N1 C1 C2 P1 135.60(17) . . . . ? O2 P1 C2 C1 -52.02(19) . . . . ? O4 P1 C2 C1 -177.63(16) . . . . ? O3 P1 C2 C1 63.97(19) . . . . ? O2 P1 C2 C3 74.02(17) . . . . ? O4 P1 C2 C3 -51.60(18) . . . . ? O3 P1 C2 C3 -170.00(15) . . . . ? C1 C2 C3 C4 -40.0(3) . . . . ? P1 C2 C3 C4 -163.06(19) . . . . ? C2 C3 C4 C5 60.6(3) . . . . ? C1 N1 C5 C4 29.1(3) . . . . ? N2 N1 C5 C4 -167.4(2) . . . . ? C3 C4 C5 N1 -52.7(3) . . . . ?