#------------------------------------------------------------------------------ #$Date: 2023-10-27 01:36:08 +0300 (Fri, 27 Oct 2023) $ #$Revision: 287127 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247583.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_7247583 loop_ _publ_author_name 'Sobczak, Paulina' 'Siera\'nski, Tomasz' 'Swiatkowski, Marcin' 'Trzesowska-Kruszynska, Agata' _publ_section_title ; New Schiff base salts as sources of blue and green light in the solid state: the role of anion and protonation ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00758H _journal_year 2023 _chemical_formula_moiety 'C15 H14 N O3, H2 O4 P' _chemical_formula_sum 'C15 H16 N O7 P' _chemical_formula_weight 353.26 _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 _atom_sites_solution_primary dual _audit_creation_date 2022-12-08 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2023-07-28 deposited with the CCDC. 2023-10-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.0910(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.99120(10) _cell_length_b 21.7863(2) _cell_length_c 9.04030(10) _cell_measurement_reflns_used 31160 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 78.7160 _cell_measurement_theta_min 4.0380 _cell_volume 1549.56(3) _computing_cell_refinement 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.956 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 40.00 125.00 0.50 0.21 -- 49.96 19.00 120.00 170 2 \w 62.00 120.00 0.50 0.21 -- 49.96 178.00-120.00 116 3 \w -26.00 25.00 0.50 0.21 -- -50.71 19.00-150.00 102 4 \w -26.00 25.00 0.50 0.21 -- -50.71 19.00 -60.00 102 5 \w -43.00 24.00 0.50 0.21 -- -50.71 38.00-180.00 134 6 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00-180.00 64 7 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00 60.00 64 8 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00-150.00 64 9 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00 90.00 64 10 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00-120.00 64 11 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00 150.00 64 12 \w -105.00 -22.00 0.50 0.26 -- -86.25 77.00 0.00 166 13 \w -158.00 -73.00 0.50 0.26 -- -86.25-125.00 60.00 170 14 \w 94.00 178.00 0.50 0.26 -- 107.75 125.00 0.00 168 15 \w 39.00 107.00 0.50 0.26 -- 107.75 -99.00 90.00 136 16 \w 37.00 66.00 0.50 0.26 -- 107.75 -57.00 0.00 58 17 \w 37.00 66.00 0.50 0.26 -- 107.75 -57.00 30.00 58 18 \w 97.00 178.00 0.50 0.26 -- 107.75 19.00 -60.00 162 19 \w 39.00 107.00 0.50 0.26 -- 107.75 -99.00 150.00 136 20 \w 37.00 66.00 0.50 0.26 -- 107.75 -57.00 -90.00 58 21 \w 37.00 66.00 0.50 0.26 -- 107.75 -57.00-180.00 58 22 \w 43.00 105.00 0.50 0.26 -- 107.75 -77.00 90.00 124 23 \w 28.00 114.00 0.50 0.21 -- 49.96 77.00 120.00 172 24 \w 28.00 114.00 0.50 0.21 -- 49.96 77.00-180.00 172 25 \w 28.00 114.00 0.50 0.21 -- 49.96 77.00 0.00 172 26 \w -115.00 -28.00 0.50 0.21 -- -50.71 -77.00 30.00 174 27 \w -115.00 -28.00 0.50 0.21 -- -50.71 -77.00 -90.00 174 28 \w -161.00 -75.00 0.50 0.26 -- -86.25 -19.00 90.00 172 29 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00-180.00 174 30 \w -161.00 -76.00 0.50 0.26 -- -86.25 -38.00-180.00 170 31 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 0.00 174 32 \w -43.00 -11.00 0.50 0.26 -- -86.25 38.00 -60.00 64 33 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 60.00 174 34 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 150.00 174 35 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 -60.00 174 36 \w -157.00 -71.00 0.50 0.26 -- -86.25 -57.00 90.00 172 37 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00-120.00 174 38 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 -90.00 174 39 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 -30.00 174 40 \w -151.00 -64.00 0.50 0.26 -- -86.25 -77.00 30.00 174 41 \w 36.00 112.00 0.50 0.26 -- 107.75-125.00 30.00 152 42 \w 37.00 66.00 0.50 0.26 -- 107.75 -57.00-120.00 58 43 \w 35.00 121.00 0.50 0.21 -- 49.96 57.00 120.00 172 44 \w 35.00 121.00 0.50 0.21 -- 49.96 57.00 -90.00 172 45 \w 35.00 115.00 0.50 0.21 -- 49.96 57.00-180.00 160 46 \w 28.00 114.00 0.50 0.21 -- 49.96 77.00 -90.00 172 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1095159000 _diffrn_orient_matrix_UB_12 -0.0586452000 _diffrn_orient_matrix_UB_13 0.0164022000 _diffrn_orient_matrix_UB_21 0.1591964000 _diffrn_orient_matrix_UB_22 0.0387322000 _diffrn_orient_matrix_UB_23 0.0581293000 _diffrn_orient_matrix_UB_31 -0.0316067000 _diffrn_orient_matrix_UB_32 -0.0079336000 _diffrn_orient_matrix_UB_33 0.1621711000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_unetI/netI 0.0147 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.956 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 37063 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.956 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.905 _diffrn_reflns_theta_min 4.058 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.946 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_correction_T_min 0.707 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.514 _exptl_crystal_description plate _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.213 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0284 _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^)+(0.0341P)^2^+0.8163P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.0742 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3075 _reflns_number_total 3198 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps010-po4 _cod_database_code 7247583 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H16 N1 O7 P1 ' _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_max 0.926 _shelx_estimated_absorpt_t_min 0.602 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C13(H13), C7(H7), C14(H14), C8(H8), C6(H6), C4(H4), C3(H3), C11(H11), C10(H10) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 2.c Idealised tetrahedral OH refined as rotating group: O7(H7A), O2(H2), O6(H6A) ; _shelx_res_file ; TITL ps010-po4_a.res in P2(1)/c ps010-po4.res created by SHELXL-2018/3 at 11:46:12 on 08-Dec-2022 REM Old TITL ps010-PO4 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.075, Rweak 0.005, Alpha 0.022 REM 0.870 for 95 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N O7 P CELL 1.54184 7.9912 21.7863 9.0403 90 100.091 90 ZERR 4 0.0001 0.0002 0.0001 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O P UNIT 60 64 4 28 4 L.S. 10 PLAN 20 SIZE 0.04 0.18 0.29 TEMP -173 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.034100 0.816300 FVAR 4.13542 P1 5 0.255758 0.000156 0.553733 11.00000 0.01372 0.01281 = 0.01060 0.00043 0.00009 0.00056 O4 4 0.142580 0.035890 0.640429 11.00000 0.01738 0.01695 = 0.01282 -0.00146 0.00107 0.00091 O5 4 0.309611 0.037260 0.427894 11.00000 0.01699 0.01617 = 0.01366 0.00226 0.00152 0.00187 O7 4 0.413837 -0.022090 0.667871 11.00000 0.01527 0.02593 = 0.01284 0.00434 0.00106 0.00247 AFIX 147 H7A 2 0.497364 -0.025781 0.623620 11.00000 -1.50000 AFIX 0 O3 4 0.099644 0.733705 0.437056 11.00000 0.02907 0.01338 = 0.01859 -0.00037 0.00043 0.00291 O2 4 0.255371 0.155336 0.423542 11.00000 0.02452 0.01310 = 0.02286 0.00186 -0.00535 0.00066 AFIX 147 H2 2 0.281241 0.118068 0.435328 11.00000 -1.50000 AFIX 0 O6 4 0.166404 -0.060609 0.489745 11.00000 0.01713 0.01290 = 0.02276 -0.00207 0.00036 0.00136 AFIX 147 H6A 2 0.066024 -0.052915 0.448538 11.00000 -1.50000 AFIX 0 O1 4 0.483296 0.168110 0.603826 11.00000 0.02582 0.01847 = 0.02750 0.00163 -0.00815 0.00356 N1 3 0.245477 0.445272 0.435826 11.00000 0.01717 0.01430 = 0.01251 0.00254 0.00095 0.00054 AFIX 43 H1 2 0.205085 0.457163 0.343439 11.00000 -1.20000 AFIX 0 C13 1 0.072451 0.631784 0.361308 11.00000 0.01886 0.01870 = 0.01243 0.00167 0.00096 0.00187 AFIX 43 H13 2 -0.000403 0.645184 0.272695 11.00000 -1.20000 AFIX 0 C5 1 0.284149 0.381729 0.458191 11.00000 0.01598 0.01429 = 0.01416 0.00176 0.00413 0.00015 C1 1 0.368052 0.189099 0.513280 11.00000 0.01693 0.01713 = 0.01453 0.00051 0.00351 0.00016 C2 1 0.338029 0.256459 0.490973 11.00000 0.01529 0.01652 = 0.01445 0.00177 0.00386 0.00070 C7 1 0.226779 0.279091 0.366910 11.00000 0.01813 0.01680 = 0.01449 0.00002 0.00105 -0.00160 AFIX 43 H7 2 0.168640 0.251527 0.294105 11.00000 -1.20000 AFIX 0 C12 1 0.140555 0.674651 0.471976 11.00000 0.01811 0.01452 = 0.01667 0.00076 0.00503 0.00170 C9 1 0.216138 0.550166 0.514326 11.00000 0.01788 0.01623 = 0.01393 0.00018 0.00215 0.00091 C14 1 0.111018 0.570767 0.381124 11.00000 0.01805 0.01726 = 0.01251 -0.00151 0.00152 -0.00024 AFIX 43 H14 2 0.066958 0.542099 0.305021 11.00000 -1.20000 AFIX 0 C8 1 0.264475 0.487201 0.539494 11.00000 0.01914 0.01834 = 0.01306 0.00117 -0.00006 0.00020 AFIX 43 H8 2 0.313741 0.475323 0.638695 11.00000 -1.20000 AFIX 0 C6 1 0.200920 0.341662 0.349669 11.00000 0.01850 0.01745 = 0.01289 0.00253 -0.00012 0.00027 AFIX 43 H6 2 0.126743 0.357208 0.264208 11.00000 -1.20000 AFIX 0 C4 1 0.398427 0.360190 0.581352 11.00000 0.01843 0.01784 = 0.01564 -0.00092 -0.00063 0.00012 AFIX 43 H4 2 0.457099 0.387873 0.653566 11.00000 -1.20000 AFIX 0 C3 1 0.424729 0.297338 0.596277 11.00000 0.01797 0.01805 = 0.01565 0.00176 -0.00105 0.00196 AFIX 43 H3 2 0.502870 0.281928 0.679367 11.00000 -1.20000 AFIX 0 C11 1 0.240771 0.655176 0.605985 11.00000 0.02066 0.01820 = 0.01495 -0.00328 0.00045 0.00007 AFIX 43 H11 2 0.284259 0.684053 0.681767 11.00000 -1.20000 AFIX 0 C10 1 0.275989 0.593242 0.627059 11.00000 0.02133 0.01923 = 0.01297 0.00052 -0.00107 0.00207 AFIX 43 H10 2 0.341611 0.579639 0.719117 11.00000 -1.20000 AFIX 0 C15 1 0.168184 0.780302 0.543351 11.00000 0.03253 0.01456 = 0.02459 -0.00355 0.00334 -0.00050 AFIX 137 H15A 2 0.125464 0.820593 0.506053 11.00000 -1.50000 H15B 2 0.292530 0.779928 0.556300 11.00000 -1.50000 H15C 2 0.133248 0.772128 0.640111 11.00000 -1.50000 AFIX 0 HKLF 4 REM ps010-po4_a.res in P2(1)/c REM wR2 = 0.0742, GooF = S = 1.066, Restrained GooF = 1.066 for all data REM R1 = 0.0284 for 3075 Fo > 4sig(Fo) and 0.0293 for all 3198 data REM 221 parameters refined using 0 restraints END WGHT 0.0341 0.8163 REM Highest difference peak 0.213, deepest hole -0.494, 1-sigma level 0.067 Q1 1 0.1629 0.0051 0.6247 11.00000 0.05 0.21 Q2 1 0.1523 0.5596 0.4581 11.00000 0.05 0.17 Q3 1 0.0910 0.0219 0.6801 11.00000 0.05 0.17 Q4 1 0.0641 0.6008 0.3890 11.00000 0.05 0.17 Q5 1 0.2340 0.6217 0.6143 11.00000 0.05 0.17 Q6 1 0.2438 0.3610 0.4033 11.00000 0.05 0.16 Q7 1 0.0983 0.0384 0.6220 11.00000 0.05 0.16 Q8 1 0.2396 0.5205 0.5234 11.00000 0.05 0.15 Q9 1 0.3496 0.2235 0.5086 11.00000 0.05 0.15 Q10 1 0.3767 0.0184 0.3801 11.00000 0.05 0.15 Q11 1 0.1562 0.0385 0.6803 11.00000 0.05 0.14 Q12 1 0.3765 0.2791 0.5397 11.00000 0.05 0.14 Q13 1 0.1239 0.6545 0.4054 11.00000 0.05 0.14 Q14 1 0.2634 0.0779 0.7173 11.00000 0.05 0.14 Q15 1 0.0883 0.7859 0.7385 11.00000 0.05 0.13 Q16 1 0.2613 0.5752 0.5649 11.00000 0.05 0.13 Q17 1 0.0943 0.7802 0.6276 11.00000 0.05 0.13 Q18 1 0.0738 0.6678 0.2429 11.00000 0.05 0.13 Q19 1 -0.1946 0.6619 0.2995 11.00000 0.05 0.13 Q20 1 0.1076 0.7200 0.7366 11.00000 0.05 0.13 ; _shelx_res_checksum 90296 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.864 _oxdiff_exptl_absorpt_empirical_full_min 0.644 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 P1 P 0.25576(3) 0.00016(2) 0.55373(3) 0.01262(9) Uani 1 1 d . . . . . O4 O 0.14258(10) 0.03589(4) 0.64043(9) 0.01591(18) Uani 1 1 d . . . . . O5 O 0.30961(10) 0.03726(4) 0.42789(9) 0.01575(18) Uani 1 1 d . . . . . O7 O 0.41384(10) -0.02209(4) 0.66787(9) 0.01818(19) Uani 1 1 d . . . . . H7A H 0.497364 -0.025781 0.623620 0.027 Uiso 1 1 calc R U . . . O3 O 0.09964(12) 0.73371(4) 0.43706(10) 0.0208(2) Uani 1 1 d . . . . . O2 O 0.25537(11) 0.15534(4) 0.42354(10) 0.0213(2) Uani 1 1 d . . . . . H2 H 0.281241 0.118068 0.435328 0.032 Uiso 1 1 calc R U . . . O6 O 0.16640(11) -0.06061(4) 0.48974(10) 0.01798(19) Uani 1 1 d . . . . . H6A H 0.066024 -0.052915 0.448538 0.027 Uiso 1 1 calc R U . . . O1 O 0.48330(12) 0.16811(4) 0.60383(11) 0.0255(2) Uani 1 1 d . . . . . N1 N 0.24548(12) 0.44527(5) 0.43583(11) 0.0149(2) Uani 1 1 d . . . . . H1 H 0.205085 0.457163 0.343439 0.018 Uiso 1 1 calc R U . . . C13 C 0.07245(15) 0.63178(6) 0.36131(13) 0.0169(2) Uani 1 1 d . . . . . H13 H -0.000403 0.645184 0.272695 0.020 Uiso 1 1 calc R U . . . C5 C 0.28415(15) 0.38173(5) 0.45819(13) 0.0146(2) Uani 1 1 d . . . . . C1 C 0.36805(15) 0.18910(6) 0.51328(13) 0.0161(2) Uani 1 1 d . . . . . C2 C 0.33803(15) 0.25646(5) 0.49097(13) 0.0153(2) Uani 1 1 d . . . . . C7 C 0.22678(15) 0.27909(6) 0.36691(13) 0.0167(2) Uani 1 1 d . . . . . H7 H 0.168640 0.251527 0.294105 0.020 Uiso 1 1 calc R U . . . C12 C 0.14055(15) 0.67465(5) 0.47198(13) 0.0162(2) Uani 1 1 d . . . . . C9 C 0.21614(15) 0.55017(6) 0.51433(13) 0.0161(2) Uani 1 1 d . . . . . C14 C 0.11102(15) 0.57077(6) 0.38112(13) 0.0161(2) Uani 1 1 d . . . . . H14 H 0.066958 0.542099 0.305021 0.019 Uiso 1 1 calc R U . . . C8 C 0.26448(15) 0.48720(6) 0.53949(13) 0.0172(2) Uani 1 1 d . . . . . H8 H 0.313741 0.475323 0.638695 0.021 Uiso 1 1 calc R U . . . C6 C 0.20092(15) 0.34166(5) 0.34967(13) 0.0166(2) Uani 1 1 d . . . . . H6 H 0.126743 0.357208 0.264208 0.020 Uiso 1 1 calc R U . . . C4 C 0.39843(15) 0.36019(6) 0.58135(13) 0.0177(2) Uani 1 1 d . . . . . H4 H 0.457099 0.387873 0.653566 0.021 Uiso 1 1 calc R U . . . C3 C 0.42473(15) 0.29734(6) 0.59628(14) 0.0177(2) Uani 1 1 d . . . . . H3 H 0.502870 0.281928 0.679367 0.021 Uiso 1 1 calc R U . . . C11 C 0.24077(15) 0.65518(6) 0.60599(14) 0.0183(3) Uani 1 1 d . . . . . H11 H 0.284259 0.684053 0.681767 0.022 Uiso 1 1 calc R U . . . C10 C 0.27599(16) 0.59324(6) 0.62706(13) 0.0183(3) Uani 1 1 d . . . . . H10 H 0.341611 0.579639 0.719117 0.022 Uiso 1 1 calc R U . . . C15 C 0.16818(18) 0.78030(6) 0.54335(15) 0.0241(3) Uani 1 1 d . . . . . H15A H 0.125464 0.820593 0.506053 0.036 Uiso 1 1 calc R U . . . H15B H 0.292530 0.779928 0.556300 0.036 Uiso 1 1 calc R U . . . H15C H 0.133248 0.772128 0.640111 0.036 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 P1 0.01372(16) 0.01281(16) 0.01060(15) 0.00043(10) 0.00009(11) 0.00056(10) O4 0.0174(4) 0.0170(4) 0.0128(4) -0.0015(3) 0.0011(3) 0.0009(3) O5 0.0170(4) 0.0162(4) 0.0137(4) 0.0023(3) 0.0015(3) 0.0019(3) O7 0.0153(4) 0.0259(5) 0.0128(4) 0.0043(3) 0.0011(3) 0.0025(3) O3 0.0291(5) 0.0134(4) 0.0186(4) -0.0004(3) 0.0004(4) 0.0029(3) O2 0.0245(5) 0.0131(4) 0.0229(5) 0.0019(3) -0.0054(4) 0.0007(3) O6 0.0171(4) 0.0129(4) 0.0228(4) -0.0021(3) 0.0004(3) 0.0014(3) O1 0.0258(5) 0.0185(4) 0.0275(5) 0.0016(4) -0.0082(4) 0.0036(4) N1 0.0172(5) 0.0143(5) 0.0125(5) 0.0025(4) 0.0010(4) 0.0005(4) C13 0.0189(6) 0.0187(6) 0.0124(5) 0.0017(5) 0.0010(4) 0.0019(5) C5 0.0160(5) 0.0143(6) 0.0142(5) 0.0018(4) 0.0041(4) 0.0002(4) C1 0.0169(6) 0.0171(6) 0.0145(5) 0.0005(4) 0.0035(4) 0.0002(4) C2 0.0153(5) 0.0165(6) 0.0145(5) 0.0018(4) 0.0039(4) 0.0007(4) C7 0.0181(6) 0.0168(6) 0.0145(6) 0.0000(4) 0.0010(4) -0.0016(4) C12 0.0181(6) 0.0145(6) 0.0167(6) 0.0008(4) 0.0050(5) 0.0017(4) C9 0.0179(5) 0.0162(6) 0.0139(5) 0.0002(4) 0.0022(4) 0.0009(4) C14 0.0180(6) 0.0173(6) 0.0125(5) -0.0015(4) 0.0015(4) -0.0002(4) C8 0.0191(6) 0.0183(6) 0.0131(6) 0.0012(4) -0.0001(5) 0.0002(5) C6 0.0185(6) 0.0174(6) 0.0129(5) 0.0025(4) -0.0001(4) 0.0003(5) C4 0.0184(6) 0.0178(6) 0.0156(6) -0.0009(5) -0.0006(5) 0.0001(5) C3 0.0180(6) 0.0181(6) 0.0157(6) 0.0018(5) -0.0010(4) 0.0020(5) C11 0.0207(6) 0.0182(6) 0.0149(6) -0.0033(5) 0.0004(5) 0.0001(5) C10 0.0213(6) 0.0192(6) 0.0130(5) 0.0005(5) -0.0011(5) 0.0021(5) C15 0.0325(7) 0.0146(6) 0.0246(7) -0.0035(5) 0.0033(5) -0.0005(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 6 0.0078 3 2 -5 0.1023 -5 -1 0 0.1268 5 1 -1 0.1495 0 14 0 0.0222 0 -14 0 0.0222 2 0 -6 0.1301 0 13 -2 0.0558 -1 14 1 0.0330 -2 8 5 0.0387 -5 -1 0 0.1265 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 O4 P1 O5 112.84(5) . . ? O4 P1 O7 107.78(5) . . ? O4 P1 O6 110.56(5) . . ? O5 P1 O7 110.96(5) . . ? O5 P1 O6 110.13(5) . . ? O7 P1 O6 104.21(5) . . ? P1 O7 H7A 109.5 . . ? C12 O3 C15 117.88(10) . . ? C1 O2 H2 109.5 . . ? P1 O6 H6A 109.5 . . ? C5 N1 H1 117.1 . . ? C8 N1 H1 117.1 . . ? C8 N1 C5 125.87(10) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C14 C13 C12 120.09(11) . . ? C6 C5 N1 116.37(10) . . ? C4 C5 N1 122.45(11) . . ? C4 C5 C6 121.18(11) . . ? O2 C1 C2 112.75(10) . . ? O1 C1 O2 124.05(11) . . ? O1 C1 C2 123.20(11) . . ? C7 C2 C1 121.37(11) . . ? C7 C2 C3 119.58(11) . . ? C3 C2 C1 119.05(10) . . ? C2 C7 H7 120.0 . . ? C6 C7 C2 120.06(11) . . ? C6 C7 H7 120.0 . . ? O3 C12 C13 114.73(10) . . ? O3 C12 C11 124.80(11) . . ? C11 C12 C13 120.47(11) . . ? C14 C9 C8 122.83(11) . . ? C10 C9 C14 118.74(11) . . ? C10 C9 C8 118.42(11) . . ? C13 C14 C9 120.38(11) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? N1 C8 C9 124.40(11) . . ? N1 C8 H8 117.8 . . ? C9 C8 H8 117.8 . . ? C5 C6 H6 120.2 . . ? C7 C6 C5 119.67(11) . . ? C7 C6 H6 120.2 . . ? C5 C4 H4 120.7 . . ? C3 C4 C5 118.50(11) . . ? C3 C4 H4 120.7 . . ? C2 C3 H3 119.5 . . ? C4 C3 C2 120.96(11) . . ? C4 C3 H3 119.5 . . ? C12 C11 H11 120.4 . . ? C10 C11 C12 119.17(11) . . ? C10 C11 H11 120.4 . . ? C9 C10 H10 119.5 . . ? C11 C10 C9 121.03(11) . . ? C11 C10 H10 119.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 P1 O4 1.5122(8) . ? P1 O5 1.5180(8) . ? P1 O7 1.5616(8) . ? P1 O6 1.5660(9) . ? O7 H7A 0.8400 . ? O3 C12 1.3512(14) . ? O3 C15 1.4386(15) . ? O2 H2 0.8400 . ? O2 C1 1.3244(15) . ? O6 H6A 0.8400 . ? O1 C1 1.2096(15) . ? N1 H1 0.8800 . ? N1 C5 1.4251(15) . ? N1 C8 1.2984(16) . ? C13 H13 0.9500 . ? C13 C12 1.4066(17) . ? C13 C14 1.3693(17) . ? C5 C6 1.3922(16) . ? C5 C4 1.3920(16) . ? C1 C2 1.4950(16) . ? C2 C7 1.3935(16) . ? C2 C3 1.3958(17) . ? C7 H7 0.9500 . ? C7 C6 1.3835(17) . ? C12 C11 1.3961(17) . ? C9 C14 1.4152(16) . ? C9 C8 1.4325(17) . ? C9 C10 1.4062(17) . ? C14 H14 0.9500 . ? C8 H8 0.9500 . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.3883(17) . ? C3 H3 0.9500 . ? C11 H11 0.9500 . ? C11 C10 1.3847(17) . ? C10 H10 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 O3 C12 C11 C10 -178.86(12) . . . . ? O2 C1 C2 C7 -12.99(16) . . . . ? O2 C1 C2 C3 167.58(11) . . . . ? O1 C1 C2 C7 166.98(12) . . . . ? O1 C1 C2 C3 -12.45(18) . . . . ? N1 C5 C6 C7 -177.40(11) . . . . ? N1 C5 C4 C3 178.20(11) . . . . ? C13 C12 C11 C10 1.65(18) . . . . ? C5 N1 C8 C9 -176.65(11) . . . . ? C5 C4 C3 C2 -0.40(19) . . . . ? C1 C2 C7 C6 179.68(11) . . . . ? C1 C2 C3 C4 -178.86(11) . . . . ? C2 C7 C6 C5 -1.17(18) . . . . ? C7 C2 C3 C4 1.70(18) . . . . ? C12 C13 C14 C9 1.52(18) . . . . ? C12 C11 C10 C9 1.65(19) . . . . ? C14 C13 C12 O3 177.21(11) . . . . ? C14 C13 C12 C11 -3.25(18) . . . . ? C14 C9 C8 N1 13.47(19) . . . . ? C14 C9 C10 C11 -3.34(18) . . . . ? C8 N1 C5 C6 157.45(12) . . . . ? C8 N1 C5 C4 -22.47(18) . . . . ? C8 C9 C14 C13 -178.26(11) . . . . ? C8 C9 C10 C11 176.65(12) . . . . ? C6 C5 C4 C3 -1.71(18) . . . . ? C4 C5 C6 C7 2.51(18) . . . . ? C3 C2 C7 C6 -0.90(18) . . . . ? C10 C9 C14 C13 1.72(18) . . . . ? C10 C9 C8 N1 -166.51(12) . . . . ? C15 O3 C12 C13 -178.51(11) . . . . ? C15 O3 C12 C11 1.98(18) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.1566 -1.2776 5.7214 0.1859 0.3080 0.9330 3.1904 1.6373 -5.1385 0.1691 0.2726 -0.9471 -5.0728 -0.7075 -0.1691 -0.5168 -0.8448 0.1385 5.1746 0.9941 -1.0254 0.4916 0.8027 -0.3377 0.4103 14.0927 -0.1876 -0.7846 0.6003 -0.1552 -0.4103 -14.0927 0.1876 0.7846 -0.6003 0.1552 1.7289 0.2383 -5.7894 0.0804 -0.0521 -0.9954 -0.0059 13.1485 -2.1247 -0.8066 0.3848 -0.4487 -1.0433 13.6775 1.0918 -0.8985 0.4271 0.1015 -1.8685 8.0625 4.6344 -0.6014 0.2842 0.7467 -5.0497 -0.6757 -0.2941 -0.5182 -0.8472 0.1173