#------------------------------------------------------------------------------ #$Date: 2021-04-20 06:56:19 +0300 (Tue, 20 Apr 2021) $ #$Revision: 264334 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158029.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_7158029 loop_ _publ_author_name 'Devi, Lalita' 'Sharma, Gaurav' 'Kant, Ruchir' 'Shukla, Sanjeev K.' 'Rastogi, Namrata' _publ_section_title ; Regioselective synthesis of functionalized pyrazole-chalcones via a base mediated reaction of diazo compounds with pyrylium salts ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00274K _journal_year 2021 _chemical_compound_source 'see text' _chemical_formula_moiety 'C26 H23 N2 O4 P' _chemical_formula_sum 'C26 H23 N2 O4 P' _chemical_formula_weight 458.43 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2020-10-16 deposited with the CCDC. 2021-03-18 downloaded from the CCDC. ; _cell_angle_alpha 83.6482(15) _cell_angle_beta 74.9958(16) _cell_angle_gamma 70.8882(16) _cell_formula_units_Z 2 _cell_length_a 8.83667(15) _cell_length_b 12.0256(2) _cell_length_c 12.1039(2) _cell_measurement_reflns_used 790 _cell_measurement_temperature 293 _cell_measurement_theta_max 68.3 _cell_measurement_theta_min 7.5 _cell_volume 1173.43(4) _computing_cell_refinement ; CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) ; _computing_data_collection ; CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) ; _computing_data_reduction ; CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) ; _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.879 _diffrn_measured_fraction_theta_max 0.879 _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (4x4 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Loop _diffrn_radiation_monochromator Confocal _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1042 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10050 _diffrn_reflns_theta_full 72.72 _diffrn_reflns_theta_max 72.72 _diffrn_reflns_theta_min 3.78 _diffrn_source MicroMax003_Cu _diffrn_source_current 0.6 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 1.328 _exptl_absorpt_correction_T_max 0.836 _exptl_absorpt_correction_T_min 0.724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Block _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.841 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.138 _refine_ls_extinction_coef 0.037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 305 _refine_ls_number_reflns 4092 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0753 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1502P)^2^+0.1654P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2085 _refine_ls_wR_factor_ref 0.2172 _reflns_number_gt 3651 _reflns_number_total 4092 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL XRF08112019a_Cu in P-1 CELL 1.54184 8.836676 12.025599 12.103866 83.6482 74.9958 70.8882 ZERR 2.00 0.000151 0.000218 0.000231 0.0015 0.0016 0.0016 LATT 1 SFAC C H N O P UNIT 52 46 4 8 2 L.S. 22 EXTI 0.03713 ACTA BOND FMAP 2 PLAN 20 SIZE 0.26 0.17 0.14 CONF WGHT 0.150200 0.165400 FVAR 12.100620 MOLE 1 C1 1 1.121615 0.383966 0.426122 11.000000 0.108770 0.069450 = 0.073650 0.002080 0.000620 -0.028050 AFIX 43 H1 2 1.030339 0.404656 0.394605 11.000000 -1.200000 AFIX 0 C2 1 1.242683 0.436938 0.384675 11.000000 0.137140 0.077230 = 0.091720 0.002700 0.011350 -0.044470 AFIX 43 H2 2 1.233879 0.491786 0.324264 11.000000 -1.200000 AFIX 0 C3 1 1.374635 0.409429 0.431606 11.000000 0.126060 0.088620 = 0.136960 -0.017120 0.028000 -0.058390 AFIX 43 H3 2 1.454319 0.447094 0.404524 11.000000 -1.200000 AFIX 0 C4 1 1.391380 0.325980 0.519210 11.000000 0.099070 0.095010 = 0.147420 -0.003730 -0.010950 -0.047900 AFIX 43 H4 2 1.483424 0.306058 0.549811 11.000000 -1.200000 AFIX 0 C5 1 1.270398 0.271747 0.561632 11.000000 0.090010 0.067420 = 0.100680 0.001770 -0.010350 -0.032120 AFIX 43 H5 2 1.280194 0.216470 0.621635 11.000000 -1.200000 AFIX 0 C6 1 1.134755 0.300395 0.514093 11.000000 0.083500 0.055270 = 0.066580 -0.008150 0.002250 -0.017980 C7 1 1.000613 0.245965 0.558838 11.000000 0.069220 0.057810 = 0.064480 -0.005630 -0.004420 -0.011040 C8 1 1.041412 0.130535 0.620772 11.000000 0.052860 0.056390 = 0.069380 -0.007040 0.000400 -0.010160 AFIX 43 H8 2 1.142643 0.075400 0.591489 11.000000 -1.200000 AFIX 0 C9 1 0.945002 0.099230 0.714963 11.000000 0.040920 0.055470 = 0.058360 -0.007670 -0.007970 -0.012930 C10 1 0.990558 -0.022818 0.761474 11.000000 0.041770 0.053570 = 0.069800 -0.007120 -0.007850 -0.016170 C11 1 1.077922 -0.117611 0.689855 11.000000 0.058720 0.058800 = 0.083280 -0.011740 -0.002580 -0.018140 AFIX 43 H11 2 1.097314 -0.105325 0.610906 11.000000 -1.200000 AFIX 0 C12 1 1.136161 -0.230052 0.735292 11.000000 0.070100 0.053930 = 0.125180 -0.010880 -0.006300 -0.015870 AFIX 43 H12 2 1.194879 -0.292745 0.686899 11.000000 -1.200000 AFIX 0 C13 1 1.106914 -0.248890 0.852470 11.000000 0.084930 0.060180 = 0.131680 0.014820 -0.033010 -0.027270 AFIX 43 H13 2 1.149613 -0.323778 0.882874 11.000000 -1.200000 AFIX 0 C14 1 1.015360 -0.157776 0.923951 11.000000 0.094390 0.069870 = 0.093400 0.014800 -0.032520 -0.037600 AFIX 43 H14 2 0.993335 -0.171483 1.002753 11.000000 -1.200000 AFIX 0 C15 1 0.955224 -0.045132 0.879611 11.000000 0.066950 0.064730 = 0.071700 -0.000750 -0.016560 -0.027980 AFIX 43 H15 2 0.890974 0.015968 0.928769 11.000000 -1.200000 AFIX 0 C16 1 0.799862 0.188468 0.781571 11.000000 0.042200 0.049250 = 0.058560 -0.006880 -0.009020 -0.012630 C17 1 0.552636 0.295076 0.875366 11.000000 0.040730 0.051070 = 0.064810 -0.009130 -0.010130 -0.012900 C18 1 0.632068 0.193822 0.811607 11.000000 0.040600 0.051160 = 0.058320 -0.008230 -0.009240 -0.013180 C19 1 0.563514 0.110399 0.776482 11.000000 0.040240 0.054250 = 0.067960 -0.011800 -0.011530 -0.012250 C20 1 0.438376 0.073740 0.849409 11.000000 0.056500 0.071350 = 0.083370 -0.021630 0.000450 -0.027110 AFIX 43 H20 2 0.393833 0.103028 0.922771 11.000000 -1.200000 AFIX 0 C21 1 0.379297 -0.006080 0.813845 11.000000 0.058860 0.078900 = 0.109380 -0.021330 -0.001610 -0.033750 AFIX 43 H21 2 0.293271 -0.028187 0.862911 11.000000 -1.200000 AFIX 0 C22 1 0.445402 -0.052680 0.708004 11.000000 0.061530 0.074730 = 0.118010 -0.032390 -0.025620 -0.018850 AFIX 43 H22 2 0.406758 -0.107736 0.685535 11.000000 -1.200000 AFIX 0 C23 1 0.567981 -0.018124 0.635711 11.000000 0.060670 0.095790 = 0.089380 -0.039290 -0.017010 -0.021930 AFIX 43 H23 2 0.613639 -0.049983 0.563444 11.000000 -1.200000 AFIX 0 C24 1 0.626103 0.064059 0.668132 11.000000 0.053200 0.082860 = 0.070340 -0.020160 -0.010600 -0.023300 AFIX 43 H24 2 0.708105 0.088450 0.616594 11.000000 -1.200000 AFIX 0 C25 1 0.091620 0.419869 0.840855 11.000000 0.065690 0.134140 = 0.114970 -0.010840 -0.035870 -0.026730 AFIX 137 H25A 2 0.051547 0.353261 0.858827 11.000000 -1.500000 H25B 2 0.070434 0.455230 0.769049 11.000000 -1.500000 H25C 2 0.036386 0.476418 0.899937 11.000000 -1.500000 AFIX 0 C26 1 0.294418 0.271385 1.133403 11.000000 0.111080 0.151720 = 0.090710 0.016250 -0.031870 -0.037560 AFIX 137 H26A 2 0.411198 0.242407 1.127042 11.000000 -1.500000 H26B 2 0.244889 0.213533 1.172905 11.000000 -1.500000 H26C 2 0.248071 0.342806 1.175344 11.000000 -1.500000 AFIX 0 H2A 2 0.648156 0.410212 0.920217 11.000000 0.090550 N1 3 0.822730 0.277810 0.825145 11.000000 0.042260 0.056260 = 0.071930 -0.013380 -0.006770 -0.015390 N2 3 0.671792 0.341399 0.880502 11.000000 0.046860 0.053640 = 0.074080 -0.014890 -0.009930 -0.015420 O1 4 0.863602 0.290930 0.540175 11.000000 0.081400 0.077740 = 0.095310 0.008750 -0.022630 -0.012280 O2 4 0.329275 0.485206 0.980666 11.000000 0.054530 0.059590 = 0.116240 -0.034730 -0.018900 -0.006050 O3 4 0.263192 0.382603 0.833125 11.000000 0.055530 0.093120 = 0.086080 -0.011060 -0.024340 -0.016330 O4 4 0.263612 0.294091 1.022759 11.000000 0.058240 0.077770 = 0.075030 -0.012340 -0.002890 -0.019920 P1 5 0.343741 0.374659 0.934860 11.000000 0.041590 0.054910 = 0.074820 -0.016510 -0.011440 -0.009630 HKLF 4 END ; _cod_data_source_file d1ob00274k2.cif _cod_data_source_block xxx _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_symmetry_cell_setting' value 'Triclinic' was changed to 'triclinic' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7158029 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z 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 0.0416(5) 0.0549(4) 0.0748(4) -0.0165(3) -0.0114(3) -0.0096(3) O1 0.0814(15) 0.0777(13) 0.0953(14) 0.0088(11) -0.0226(11) -0.0123(11) O2 0.0545(11) 0.0596(10) 0.1162(14) -0.0347(10) -0.0189(10) -0.0060(9) O3 0.0555(11) 0.0931(13) 0.0861(12) -0.0111(10) -0.0243(9) -0.0163(10) O4 0.0582(11) 0.0778(11) 0.0750(10) -0.0123(9) -0.0029(8) -0.0199(9) N1 0.0423(12) 0.0563(10) 0.0719(11) -0.0134(9) -0.0068(9) -0.0154(9) N2 0.0469(12) 0.0536(10) 0.0741(11) -0.0149(9) -0.0099(9) -0.0154(9) C1 0.109(3) 0.0695(16) 0.0737(15) 0.0021(13) 0.0006(16) -0.0280(17) C2 0.137(4) 0.077(2) 0.092(2) 0.0027(17) 0.011(2) -0.044(2) C3 0.126(4) 0.089(2) 0.137(3) -0.017(2) 0.028(3) -0.058(3) C4 0.099(3) 0.095(2) 0.147(3) -0.004(2) -0.011(2) -0.048(2) C5 0.090(2) 0.0674(16) 0.101(2) 0.0018(15) -0.0104(17) -0.0321(16) C6 0.084(2) 0.0553(13) 0.0666(13) -0.0082(10) 0.0023(13) -0.0180(14) C7 0.0692(18) 0.0578(13) 0.0645(13) -0.0056(10) -0.0044(12) -0.0110(12) C8 0.0529(15) 0.0564(12) 0.0694(13) -0.0070(10) 0.0004(11) -0.0102(11) C9 0.0409(12) 0.0555(11) 0.0584(10) -0.0077(9) -0.0080(9) -0.0129(10) C10 0.0418(12) 0.0536(12) 0.0698(12) -0.0071(10) -0.0078(10) -0.0162(10) C11 0.0587(16) 0.0588(13) 0.0833(15) -0.0117(12) -0.0026(12) -0.0181(12) C12 0.070(2) 0.0539(14) 0.125(3) -0.0109(15) -0.0063(17) -0.0159(14) C13 0.085(2) 0.0602(15) 0.132(3) 0.0148(17) -0.033(2) -0.0273(16) C14 0.094(2) 0.0699(16) 0.0934(18) 0.0148(14) -0.0325(17) -0.0376(16) C15 0.0670(16) 0.0647(13) 0.0717(13) -0.0007(11) -0.0166(12) -0.0280(12) C16 0.0422(12) 0.0492(10) 0.0586(10) -0.0069(8) -0.0090(9) -0.0126(10) C17 0.0407(13) 0.0511(11) 0.0648(11) -0.0091(9) -0.0101(9) -0.0129(10) C18 0.0406(12) 0.0512(10) 0.0583(10) -0.0082(9) -0.0092(9) -0.0132(9) C19 0.0402(12) 0.0543(11) 0.0680(12) -0.0118(9) -0.0115(9) -0.0123(10) C20 0.0565(16) 0.0714(15) 0.0834(15) -0.0216(12) 0.0005(12) -0.0271(13) C21 0.0589(17) 0.0789(17) 0.109(2) -0.0213(15) -0.0016(15) -0.0337(15) C22 0.0615(18) 0.0747(16) 0.118(2) -0.0324(16) -0.0256(16) -0.0189(14) C23 0.0607(17) 0.096(2) 0.0894(17) -0.0393(15) -0.0170(13) -0.0219(15) C24 0.0532(15) 0.0829(16) 0.0703(13) -0.0202(12) -0.0106(11) -0.0233(13) C25 0.066(2) 0.134(3) 0.115(2) -0.011(2) -0.0359(18) -0.027(2) C26 0.111(3) 0.152(4) 0.091(2) 0.016(2) -0.032(2) -0.038(3) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags P1 P Uani 0.34374(7) 0.37466(5) 0.93486(5) 1.000 0.0578(3) . . O1 O Uani 0.8636(3) 0.29093(19) 0.54018(19) 1.000 0.0885(8) . . O2 O Uani 0.3293(2) 0.48521(15) 0.98067(19) 1.000 0.0774(7) . . O3 O Uani 0.2632(2) 0.38260(18) 0.83313(17) 1.000 0.0778(7) . . O4 O Uani 0.2636(2) 0.29409(17) 1.02276(15) 1.000 0.0723(6) . . N1 N Uani 0.8227(2) 0.27781(17) 0.82515(16) 1.000 0.0572(6) . . N2 N Uani 0.6718(2) 0.34140(17) 0.88050(17) 1.000 0.0581(6) . . C1 C Uani 1.1216(5) 0.3840(3) 0.4261(2) 1.000 0.0887(12) . . C2 C Uani 1.2427(7) 0.4369(3) 0.3847(3) 1.000 0.1072(16) . . C3 C Uani 1.3746(7) 0.4094(4) 0.4316(4) 1.000 0.1216(18) . . C4 C Uani 1.3914(6) 0.3260(4) 0.5192(4) 1.000 0.1127(16) . . C5 C Uani 1.2704(4) 0.2717(3) 0.5616(3) 1.000 0.0869(11) . . C6 C Uani 1.1348(4) 0.3004(2) 0.5141(2) 1.000 0.0730(9) . . C7 C Uani 1.0006(4) 0.2460(2) 0.5588(2) 1.000 0.0680(9) . . C8 C Uani 1.0414(3) 0.1305(2) 0.6208(2) 1.000 0.0638(8) . . C9 C Uani 0.9450(3) 0.09923(19) 0.71496(18) 1.000 0.0524(6) . . C10 C Uani 0.9906(3) -0.02282(19) 0.76147(19) 1.000 0.0554(7) . . C11 C Uani 1.0779(3) -0.1176(2) 0.6899(2) 1.000 0.0690(8) . . C12 C Uani 1.1362(4) -0.2301(2) 0.7353(3) 1.000 0.0864(13) . . C13 C Uani 1.1069(4) -0.2489(3) 0.8525(3) 1.000 0.0912(13) . . C14 C Uani 1.0154(4) -0.1578(3) 0.9240(3) 1.000 0.0821(10) . . C15 C Uani 0.9552(3) -0.0451(2) 0.8796(2) 1.000 0.0660(8) . . C16 C Uani 0.7999(3) 0.18847(18) 0.78157(18) 1.000 0.0506(6) . . C17 C Uani 0.5526(3) 0.29508(18) 0.87537(18) 1.000 0.0524(7) . . C18 C Uani 0.6321(3) 0.19382(18) 0.81161(17) 1.000 0.0503(6) . . C19 C Uani 0.5635(3) 0.11040(19) 0.77648(19) 1.000 0.0542(7) . . C20 C Uani 0.4384(3) 0.0737(2) 0.8494(2) 1.000 0.0704(9) . . C21 C Uani 0.3793(4) -0.0061(3) 0.8138(3) 1.000 0.0812(10) . . C22 C Uani 0.4454(4) -0.0527(3) 0.7080(3) 1.000 0.0821(10) . . C23 C Uani 0.5680(4) -0.0181(3) 0.6357(3) 1.000 0.0799(10) . . C24 C Uani 0.6261(3) 0.0641(2) 0.6681(2) 1.000 0.0676(8) . . C25 C Uani 0.0916(4) 0.4199(4) 0.8409(3) 1.000 0.1026(14) . . C26 C Uani 0.2944(6) 0.2714(5) 1.1334(3) 1.000 0.1187(18) . . H1 H Uiso 1.03030 0.40470 0.39460 1.000 0.1060 calc R H2 H Uiso 1.23390 0.49180 0.32430 1.000 0.1290 calc R H2A H Uiso 0.648(4) 0.410(3) 0.920(3) 1.000 0.091(9) . . H3 H Uiso 1.45430 0.44710 0.40450 1.000 0.1460 calc R H4 H Uiso 1.48340 0.30610 0.54980 1.000 0.1350 calc R H5 H Uiso 1.28020 0.21650 0.62160 1.000 0.1040 calc R H8 H Uiso 1.14260 0.07540 0.59150 1.000 0.0760 calc R H11 H Uiso 1.09730 -0.10530 0.61090 1.000 0.0830 calc R H12 H Uiso 1.19490 -0.29270 0.68690 1.000 0.1040 calc R H13 H Uiso 1.14960 -0.32380 0.88290 1.000 0.1090 calc R H14 H Uiso 0.99330 -0.17150 1.00280 1.000 0.0990 calc R H15 H Uiso 0.89100 0.01600 0.92880 1.000 0.0790 calc R H20 H Uiso 0.39380 0.10300 0.92280 1.000 0.0840 calc R H21 H Uiso 0.29330 -0.02820 0.86290 1.000 0.0980 calc R H22 H Uiso 0.40680 -0.10770 0.68550 1.000 0.0990 calc R H23 H Uiso 0.61360 -0.05000 0.56340 1.000 0.0960 calc R H24 H Uiso 0.70810 0.08850 0.61660 1.000 0.0810 calc R H25A H Uiso 0.05150 0.35330 0.85880 1.000 0.1540 calc R H25B H Uiso 0.07040 0.45520 0.76900 1.000 0.1540 calc R H25C H Uiso 0.03640 0.47640 0.89990 1.000 0.1540 calc R H26A H Uiso 0.41120 0.24240 1.12700 1.000 0.1780 calc R H26B H Uiso 0.24490 0.21350 1.17290 1.000 0.1780 calc R H26C H Uiso 0.24810 0.34280 1.17530 1.000 0.1780 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' C C 0.0181 0.0091 '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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O3 116.76(12) . . . yes O2 P1 O4 114.00(12) . . . yes O2 P1 C17 111.40(12) . . . yes O3 P1 O4 102.51(11) . . . yes O3 P1 C17 101.94(11) . . . yes O4 P1 C17 109.20(10) . . . yes P1 O3 C25 125.0(2) . . . yes P1 O4 C26 120.9(3) . . . yes N2 N1 C16 105.01(19) . . . yes N1 N2 C17 112.89(18) . . . yes C17 N2 H2A 122(2) . . . no N1 N2 H2A 125(2) . . . no C2 C1 C6 120.5(4) . . . no C1 C2 C3 120.3(4) . . . no C2 C3 C4 120.5(5) . . . no C3 C4 C5 119.8(5) . . . no C4 C5 C6 119.7(3) . . . no C1 C6 C5 119.2(3) . . . no C1 C6 C7 119.4(3) . . . no C5 C6 C7 121.4(2) . . . no O1 C7 C6 121.7(2) . . . yes C6 C7 C8 117.8(3) . . . no O1 C7 C8 120.4(3) . . . yes C7 C8 C9 125.4(2) . . . no C8 C9 C16 120.8(2) . . . no C10 C9 C16 118.55(19) . . . no C8 C9 C10 120.4(2) . . . no C11 C10 C15 118.4(2) . . . no C9 C10 C11 121.2(2) . . . no C9 C10 C15 120.3(2) . . . no C10 C11 C12 120.6(2) . . . no C11 C12 C13 119.9(3) . . . no C12 C13 C14 120.3(3) . . . no C13 C14 C15 120.3(3) . . . no C10 C15 C14 120.4(2) . . . no N1 C16 C18 111.42(19) . . . yes N1 C16 C9 119.1(2) . . . yes C9 C16 C18 129.5(2) . . . no N2 C17 C18 106.4(2) . . . yes P1 C17 C18 134.8(2) . . . yes P1 C17 N2 118.60(16) . . . yes C16 C18 C17 104.3(2) . . . no C16 C18 C19 125.7(2) . . . no C17 C18 C19 130.0(2) . . . no C18 C19 C20 122.3(2) . . . no C20 C19 C24 117.6(2) . . . no C18 C19 C24 120.1(2) . . . no C19 C20 C21 120.5(2) . . . no C20 C21 C22 120.9(3) . . . no C21 C22 C23 119.4(3) . . . no C22 C23 C24 120.8(3) . . . no C19 C24 C23 120.8(3) . . . no C2 C1 H1 120.00 . . . no C6 C1 H1 120.00 . . . no C1 C2 H2 120.00 . . . no C3 C2 H2 120.00 . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C7 C8 H8 117.00 . . . no C9 C8 H8 117.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C10 C15 H15 120.00 . . . no C14 C15 H15 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 120.00 . . . no C20 C21 H21 120.00 . . . no C22 C21 H21 120.00 . . . no C21 C22 H22 120.00 . . . no C23 C22 H22 120.00 . . . no C22 C23 H23 120.00 . . . no C24 C23 H23 120.00 . . . no C19 C24 H24 120.00 . . . no C23 C24 H24 120.00 . . . no O3 C25 H25A 109.00 . . . no O3 C25 H25B 109.00 . . . no O3 C25 H25C 110.00 . . . no H25A C25 H25B 109.00 . . . no H25A C25 H25C 110.00 . . . no H25B C25 H25C 110.00 . . . no O4 C26 H26A 109.00 . . . no O4 C26 H26B 109.00 . . . no O4 C26 H26C 109.00 . . . no H26A C26 H26B 109.00 . . . no H26A C26 H26C 109.00 . . . no H26B C26 H26C 110.00 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.4514(19) . . yes P1 O3 1.554(2) . . yes P1 O4 1.550(2) . . yes P1 C17 1.774(3) . . yes O1 C7 1.222(4) . . yes O3 C25 1.414(4) . . yes O4 C26 1.415(4) . . yes N1 N2 1.340(3) . . yes N1 C16 1.340(3) . . yes N2 C17 1.360(3) . . yes N2 H2A 0.94(4) . . no C1 C2 1.378(7) . . no C1 C6 1.382(4) . . no C2 C3 1.356(9) . . no C3 C4 1.379(7) . . no C4 C5 1.390(7) . . no C5 C6 1.388(5) . . no C6 C7 1.492(5) . . no C7 C8 1.485(3) . . no C8 C9 1.334(3) . . no C9 C10 1.477(3) . . no C9 C16 1.484(3) . . no C10 C15 1.397(3) . . no C10 C11 1.393(3) . . no C11 C12 1.387(3) . . no C12 C13 1.381(5) . . no C13 C14 1.368(5) . . no C14 C15 1.387(4) . . no C16 C18 1.414(4) . . no C17 C18 1.393(3) . . no C18 C19 1.477(4) . . no C19 C24 1.386(3) . . no C19 C20 1.387(4) . . no C20 C21 1.384(4) . . no C21 C22 1.361(5) . . no C22 C23 1.355(5) . . no C23 C24 1.385(4) . . no C1 H1 0.9300 . . no C2 H2 0.9300 . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C5 H5 0.9300 . . no C8 H8 0.9300 . . no C11 H11 0.9300 . . no C12 H12 0.9300 . . no C13 H13 0.9300 . . no C14 H14 0.9300 . . no C15 H15 0.9300 . . no C20 H20 0.9300 . . no C21 H21 0.9300 . . no C22 H22 0.9300 . . no C23 H23 0.9300 . . no C24 H24 0.9300 . . no C25 H25A 0.9600 . . no C25 H25B 0.9600 . . no C25 H25C 0.9600 . . no C26 H26A 0.9600 . . no C26 H26B 0.9600 . . no C26 H26C 0.9600 . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag P1 C20 3.642(2) . . no P1 H20 3.1600 . . no O1 C16 3.030(3) . . no O1 C2 3.260(4) . 2_766 no O2 N2 2.815(3) . 2_667 no O2 N2 2.959(3) . . no O4 C20 3.269(3) . . no O4 C14 3.282(4) . 2_657 no O1 H11 2.9200 . 2_756 no O1 H1 2.5700 . . no O2 H13 2.6800 . 1_465 no O2 H2A 1.92(4) . 2_667 no O2 H26C 2.8300 . . no O2 H2A 2.59(4) . . no O4 H20 2.5000 . . no N1 C7 3.204(3) . . no N1 C25 3.401(5) . 1_655 no N2 O2 2.815(3) . 2_667 no N2 O2 2.959(3) . . no N1 H14 2.9000 . 2_757 no N1 H25A 2.6100 . 1_655 no C1 C1 3.285(5) . 2_766 no C2 O1 3.260(4) . 2_766 no C7 N1 3.204(3) . . no C9 C24 3.178(4) . . no C10 C19 3.549(4) . . no C10 C24 3.488(4) . . no C14 O4 3.282(4) . 2_657 no C15 C18 3.522(3) . . no C15 C15 3.572(4) . 2_757 no C16 O1 3.030(3) . . no C18 C15 3.522(3) . . no C19 C10 3.549(4) . . no C20 P1 3.642(2) . . no C20 O4 3.269(3) . . no C24 C10 3.488(4) . . no C24 C9 3.178(4) . . no C25 N1 3.401(5) . 1_455 no C1 H26C 2.9900 . 1_654 no C2 H26C 2.8700 . 1_654 no C5 H8 2.8900 . . no C5 H23 2.9600 . 2_756 no C8 H11 2.7300 . . no C8 H5 2.6400 . . no C9 H24 2.7100 . . no C11 H8 2.6500 . . no C11 H22 2.9300 . 1_655 no C12 H22 3.1000 . 1_655 no C13 H26B 3.0900 . 2_657 no C14 H15 3.0200 . 2_757 no C15 H21 3.0100 . 1_655 no C15 H15 3.0800 . 2_757 no C16 H24 2.8500 . . no C16 H15 2.6400 . . no C17 H20 3.0100 . . no C17 H26A 3.0600 . . no C21 H26A 2.9700 . 2_657 no C22 H26A 3.0300 . 2_657 no H1 O1 2.5700 . . no H1 H25B 2.6000 . 2_666 no H2A O2 2.59(4) . . no H2A O2 1.92(4) . 2_667 no H5 C8 2.6400 . . no H5 H8 2.4900 . . no H8 C5 2.8900 . . no H8 C11 2.6500 . . no H8 H5 2.4900 . . no H8 H11 2.3100 . . no H8 H23 2.4200 . 2_756 no H11 C8 2.7300 . . no H11 H8 2.3100 . . no H11 O1 2.9200 . 2_756 no H13 O2 2.6800 . 1_645 no H14 N1 2.9000 . 2_757 no H15 C16 2.6400 . . no H15 C14 3.0200 . 2_757 no H15 C15 3.0800 . 2_757 no H20 P1 3.1600 . . no H20 O4 2.5000 . . no H20 C17 3.0100 . . no H21 C15 3.0100 . 1_455 no H22 C11 2.9300 . 1_455 no H22 C12 3.1000 . 1_455 no H23 C5 2.9600 . 2_756 no H23 H8 2.4200 . 2_756 no H24 C9 2.7100 . . no H24 C16 2.8500 . . no H25A N1 2.6100 . 1_455 no H25B H1 2.6000 . 2_666 no H25C H25C 2.4200 . 2_567 no H26A C17 3.0600 . . no H26A C21 2.9700 . 2_657 no H26A C22 3.0300 . 2_657 no H26B C13 3.0900 . 2_657 no H26C O2 2.8300 . . no H26C C1 2.9900 . 1_456 no H26C C2 2.8700 . 1_456 no 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 N2 H2A O2 0.94(4) 2.59(4) 2.959(3) 104(3) . yes N2 H2A O2 0.94(4) 1.92(4) 2.815(3) 159(3) 2_667 yes C20 H20 O4 0.9300 2.5000 3.269(3) 141.00 . yes C25 H25A N1 0.9600 2.6100 3.401(5) 140.00 1_455 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 O2 P1 O3 C25 -70.0(3) . . . . no O4 P1 O3 C25 55.4(3) . . . . no C17 P1 O3 C25 168.4(3) . . . . no O2 P1 O4 C26 -47.9(3) . . . . no O3 P1 O4 C26 -175.0(3) . . . . no C17 P1 O4 C26 77.4(3) . . . . no O4 P1 C17 N2 -125.43(17) . . . . no O2 P1 C17 N2 1.4(2) . . . . no O3 P1 C17 N2 126.62(18) . . . . no O4 P1 C17 C18 61.3(2) . . . . no O2 P1 C17 C18 -171.9(2) . . . . no O3 P1 C17 C18 -46.7(2) . . . . no C16 N1 N2 C17 0.9(2) . . . . no N2 N1 C16 C18 -1.2(2) . . . . no N2 N1 C16 C9 -179.39(19) . . . . no N1 N2 C17 C18 -0.1(3) . . . . no N1 N2 C17 P1 -175.18(15) . . . . no C2 C1 C6 C7 178.9(3) . . . . no C6 C1 C2 C3 -1.5(5) . . . . no C2 C1 C6 C5 1.0(4) . . . . no C1 C2 C3 C4 1.7(6) . . . . no C2 C3 C4 C5 -1.5(7) . . . . no C3 C4 C5 C6 1.1(6) . . . . no C4 C5 C6 C1 -0.9(5) . . . . no C4 C5 C6 C7 -178.7(3) . . . . no C1 C6 C7 O1 -17.5(4) . . . . no C5 C6 C7 O1 160.3(3) . . . . no C5 C6 C7 C8 -23.6(3) . . . . no C1 C6 C7 C8 158.5(2) . . . . no C6 C7 C8 C9 139.5(3) . . . . no O1 C7 C8 C9 -44.4(4) . . . . no C7 C8 C9 C10 173.0(3) . . . . no C7 C8 C9 C16 -13.4(4) . . . . no C16 C9 C10 C15 -29.0(4) . . . . no C8 C9 C16 N1 -59.3(3) . . . . no C8 C9 C16 C18 123.0(3) . . . . no C10 C9 C16 N1 114.5(3) . . . . no C8 C9 C10 C11 -31.4(4) . . . . no C10 C9 C16 C18 -63.3(3) . . . . no C8 C9 C10 C15 144.8(3) . . . . no C16 C9 C10 C11 154.8(3) . . . . no C9 C10 C15 C14 -172.1(3) . . . . no C11 C10 C15 C14 4.2(4) . . . . no C9 C10 C11 C12 172.6(3) . . . . no C15 C10 C11 C12 -3.7(4) . . . . no C10 C11 C12 C13 0.4(5) . . . . no C11 C12 C13 C14 2.4(6) . . . . no C12 C13 C14 C15 -1.9(6) . . . . no C13 C14 C15 C10 -1.5(5) . . . . no N1 C16 C18 C17 1.2(2) . . . . no C9 C16 C18 C17 179.1(2) . . . . no C9 C16 C18 C19 -3.1(4) . . . . no N1 C16 C18 C19 179.0(2) . . . . no P1 C17 C18 C16 173.27(19) . . . . no P1 C17 C18 C19 -4.4(4) . . . . no N2 C17 C18 C16 -0.6(2) . . . . no N2 C17 C18 C19 -178.3(2) . . . . no C16 C18 C19 C20 141.8(2) . . . . no C16 C18 C19 C24 -37.0(3) . . . . no C17 C18 C19 C20 -41.0(4) . . . . no C17 C18 C19 C24 140.2(2) . . . . no C18 C19 C20 C21 -179.0(3) . . . . no C24 C19 C20 C21 -0.2(4) . . . . no C18 C19 C24 C23 177.2(3) . . . . no C20 C19 C24 C23 -1.7(4) . . . . no C19 C20 C21 C22 1.8(5) . . . . no C20 C21 C22 C23 -1.6(5) . . . . no C21 C22 C23 C24 -0.2(5) . . . . no C22 C23 C24 C19 1.9(5) . . . . no