#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:43 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288773 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247582.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_7247582 loop_ _publ_author_name 'Sobczak, Paulina' 'Siera\'nski, Tomasz' '\'Swi\;atkowski, Marcin' 'Trz\;esowska-Kruszy\'nska, Agata' _publ_section_title ; New Schiff base salts as sources of blue and green light in the solid state: the role of the anion and protonation ; _journal_issue 44 _journal_name_full CrystEngComm _journal_page_first 6185 _journal_page_last 6193 _journal_paper_doi 10.1039/D3CE00758H _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C15 H14 N O3, Cl, H2 O' _chemical_formula_sum 'C15 H16 Cl N O4' _chemical_formula_weight 309.74 _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 mixed _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 92.1960(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.70370(10) _cell_length_b 20.9656(3) _cell_length_c 14.8427(2) _cell_measurement_reflns_used 7863 _cell_measurement_temperature 100.00(13) _cell_measurement_theta_max 78.5710 _cell_measurement_theta_min 3.6380 _cell_volume 1462.65(4) _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 100.00(13) _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 0.936 _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 -25.00 43.00 0.50 1.50 -- 49.96 -38.00 150.00 136 2 \w 36.00 117.00 0.50 4.00 -- 107.75-125.00 30.00 162 3 \w 43.00 105.00 0.50 4.00 -- 107.75 -77.00 -60.00 124 4 \w 43.00 105.00 0.50 4.00 -- 107.75 -77.00-150.00 124 5 \w 97.00 178.00 0.50 4.00 -- 107.75 19.00 30.00 162 6 \w 93.00 178.00 0.50 4.00 -- 107.75 57.00 -30.00 170 7 \w 39.00 110.00 0.50 4.00 -- 107.75 -99.00 60.00 142 8 \w 35.00 121.00 0.50 1.50 -- 49.96 57.00 90.00 172 9 \w 28.00 114.00 0.50 1.50 -- 49.96 77.00 0.00 172 10 \w -25.00 26.00 0.50 1.50 -- 49.96 -19.00 -90.00 102 11 \w -26.00 25.00 0.50 1.50 -- -50.71 19.00-180.00 102 12 \w -43.00 -11.00 0.50 4.00 -- -86.25 38.00 -30.00 64 13 \w -66.00 -15.00 0.50 4.00 -- -86.25 57.00 90.00 102 14 \w -92.00 -15.00 0.50 4.00 -- -86.25 125.00 30.00 154 15 \w -92.00 -15.00 0.50 4.00 -- -86.25 125.00 90.00 154 16 \w -126.00 -40.00 0.50 1.50 -- -50.71 -19.00-120.00 172 17 \w -122.00 -36.00 0.50 1.50 -- -50.71 -57.00-180.00 172 18 \w -161.00-120.00 0.50 4.00 -- -86.25 -19.00-150.00 82 19 \w -157.00 -71.00 0.50 4.00 -- -86.25 -57.00 120.00 172 ; _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 0.0105595000 _diffrn_orient_matrix_UB_12 -0.0612057000 _diffrn_orient_matrix_UB_13 -0.0572196000 _diffrn_orient_matrix_UB_21 -0.0437591000 _diffrn_orient_matrix_UB_22 -0.0405274000 _diffrn_orient_matrix_UB_23 0.0849466000 _diffrn_orient_matrix_UB_31 -0.3246003000 _diffrn_orient_matrix_UB_32 0.0034836000 _diffrn_orient_matrix_UB_33 -0.0172954000 _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 0.0296 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.936 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14629 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.936 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.411 _diffrn_reflns_theta_min 3.650 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.458 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_correction_T_min 0.781 _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 1.407 _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.794 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2923 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0392 _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^)+(0.0459P)^2^+1.4067P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.1029 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2579 _reflns_number_total 2923 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps10_1 _cod_depositor_comments 'Adding full bibliography for 7247579--7247585.cif.' _cod_database_code 7247582 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H16 Cl1 N1 O4' _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 0.952 _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, All O(H,H) groups 2.a Riding coordinates: O4(H4A,H4B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1A), C6(H6), C7(H7), C13(H13), C14(H14), C8(H8), C11(H11), C10(H10), C4(H4), C3(H3) 2.c Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL ps10_1_a.res in P2(1)/c ps10_1.res created by SHELXL-2018/3 at 11:55:26 on 08-Dec-2022 REM Old TITL ps10_1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.088, Rweak 0.020, Alpha 0.026 REM 0.833 for 92 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N2 O3 Cl CELL 1.54184 4.7037 20.9656 14.8427 90 92.196 90 ZERR 4 0.0001 0.0003 0.0002 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 60 64 4 4 16 L.S. 10 PLAN 20 SIZE 0.02 0.03 0.23 TEMP -173 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.045900 1.406700 FVAR 2.26216 CL1 3 1.819715 0.707277 0.650662 11.00000 0.01968 0.02135 = 0.01332 -0.00025 0.00094 -0.00155 O3 5 -0.717137 0.054495 0.534094 11.00000 0.01644 0.01990 = 0.01846 0.00150 -0.00282 -0.00632 O2 5 1.230683 0.462621 0.754443 11.00000 0.02286 0.02654 = 0.02498 -0.00433 -0.00079 -0.00597 O1 5 1.094492 0.495617 0.616212 11.00000 0.03732 0.02420 = 0.02821 0.00365 -0.00393 -0.01407 AFIX 147 H1 2 1.201888 0.526591 0.629003 11.00000 -1.50000 AFIX 0 N1 4 0.253627 0.260016 0.647472 11.00000 0.01648 0.01714 = 0.01553 -0.00116 0.00082 0.00117 AFIX 43 H1A 2 0.223816 0.238768 0.697362 11.00000 -1.20000 AFIX 0 O4 5 1.323448 0.607445 0.639408 11.00000 0.02818 0.02400 = 0.03657 -0.00231 0.00084 -0.00399 AFIX 3 H4A 2 1.479258 0.629855 0.642578 11.00000 -1.50000 H4B 2 1.187798 0.635594 0.636398 11.00000 -1.50000 AFIX 0 C12 1 -0.518164 0.099837 0.550877 11.00000 0.01193 0.01522 = 0.01844 -0.00218 0.00208 0.00010 C9 1 -0.109720 0.195355 0.571382 11.00000 0.01374 0.01439 = 0.02238 -0.00221 0.00308 0.00031 C5 1 0.466037 0.309437 0.651859 11.00000 0.01245 0.01575 = 0.01845 -0.00494 0.00099 0.00065 C2 1 0.874327 0.404521 0.672387 11.00000 0.01285 0.01760 = 0.01639 -0.00407 0.00243 0.00065 C6 1 0.620251 0.315483 0.733357 11.00000 0.01517 0.01817 = 0.01540 -0.00076 0.00138 0.00036 AFIX 43 H6 2 0.585808 0.287342 0.781904 11.00000 -1.20000 AFIX 0 C7 1 0.824237 0.362853 0.743065 11.00000 0.01367 0.01941 = 0.01415 -0.00319 -0.00111 -0.00063 AFIX 43 H7 2 0.930906 0.366954 0.798416 11.00000 -1.20000 AFIX 0 C1 1 1.086622 0.456399 0.686865 11.00000 0.01572 0.01635 = 0.01945 -0.00482 0.00277 -0.00103 C13 1 -0.372969 0.107482 0.634295 11.00000 0.01640 0.01718 = 0.01636 0.00104 0.00019 -0.00058 AFIX 43 H13 2 -0.412716 0.080299 0.683450 11.00000 -1.20000 AFIX 0 C14 1 -0.171596 0.154979 0.644129 11.00000 0.01839 0.01858 = 0.01913 -0.00207 -0.00264 0.00054 AFIX 43 H14 2 -0.073114 0.160613 0.700649 11.00000 -1.20000 AFIX 0 C15 1 -0.773494 0.010668 0.605324 11.00000 0.01713 0.01823 = 0.02020 0.00245 -0.00238 -0.00502 AFIX 137 H15A 2 -0.922862 -0.019198 0.585006 11.00000 -1.50000 H15B 2 -0.836453 0.034313 0.657911 11.00000 -1.50000 H15C 2 -0.599704 -0.013081 0.621763 11.00000 -1.50000 AFIX 0 C8 1 0.102307 0.244207 0.575889 11.00000 0.01607 0.01699 = 0.01627 -0.00107 0.00110 0.00222 AFIX 43 H8 2 0.135341 0.267035 0.522000 11.00000 -1.20000 AFIX 0 C11 1 -0.464274 0.140580 0.478438 11.00000 0.01815 0.02154 = 0.01564 -0.00041 -0.00064 -0.00025 AFIX 43 H11 2 -0.567821 0.135809 0.422628 11.00000 -1.20000 AFIX 0 C10 1 -0.261392 0.187323 0.488595 11.00000 0.01806 0.01901 = 0.01720 0.00059 0.00348 0.00072 AFIX 43 H10 2 -0.222995 0.214499 0.439309 11.00000 -1.20000 AFIX 0 C4 1 0.516535 0.349611 0.580062 11.00000 0.02064 0.02363 = 0.01540 -0.00328 -0.00379 -0.00081 AFIX 43 H4 2 0.412965 0.344609 0.524298 11.00000 -1.20000 AFIX 0 C3 1 0.720055 0.397221 0.590536 11.00000 0.02365 0.02338 = 0.01452 0.00176 0.00043 -0.00011 AFIX 43 H3 2 0.754958 0.425098 0.541727 11.00000 -1.20000 AFIX 0 HKLF 4 REM ps10_1_a.res in P2(1)/c REM wR2 = 0.1029, GooF = S = 1.044, Restrained GooF = 1.044 for all data REM R1 = 0.0392 for 2579 Fo > 4sig(Fo) and 0.0460 for all 2923 data REM 192 parameters refined using 0 restraints END WGHT 0.0459 1.4064 REM Highest difference peak 0.794, deepest hole -0.275, 1-sigma level 0.056 Q1 1 -0.8232 0.0599 0.4594 11.00000 0.05 0.79 Q2 1 1.5468 0.5741 0.6188 11.00000 0.05 0.40 Q3 1 -0.3430 0.1575 0.4948 11.00000 0.05 0.36 Q4 1 0.2668 0.2802 0.5958 11.00000 0.05 0.34 Q5 1 -0.1026 0.1812 0.6168 11.00000 0.05 0.31 Q6 1 1.6546 0.7219 0.6432 11.00000 0.05 0.29 Q7 1 -0.1376 0.1821 0.5237 11.00000 0.05 0.29 Q8 1 0.8275 0.4008 0.6322 11.00000 0.05 0.29 Q9 1 0.6942 0.3411 0.7367 11.00000 0.05 0.29 Q10 1 0.9480 0.4343 0.6828 11.00000 0.05 0.29 Q11 1 -0.2178 0.1966 0.5370 11.00000 0.05 0.28 Q12 1 0.4783 0.3375 0.6227 11.00000 0.05 0.27 Q13 1 0.1330 0.2271 0.6443 11.00000 0.05 0.27 Q14 1 0.8491 0.3822 0.7045 11.00000 0.05 0.27 Q15 1 0.5789 0.3109 0.6883 11.00000 0.05 0.26 Q16 1 -0.4206 0.1004 0.5840 11.00000 0.05 0.25 Q17 1 0.5163 0.3200 0.6964 11.00000 0.05 0.25 Q18 1 -0.0375 0.2170 0.5729 11.00000 0.05 0.24 Q19 1 0.5793 0.3790 0.5793 11.00000 0.05 0.24 Q20 1 0.6639 0.3621 0.5790 11.00000 0.05 0.21 ; _shelx_res_checksum 88071 _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 1.280 _oxdiff_exptl_absorpt_empirical_full_min 0.556 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 Cl1 Cl 1.81971(9) 0.70728(2) 0.65066(3) 0.01811(13) Uani 1 1 d . . . . . O3 O -0.7171(3) 0.05449(6) 0.53409(8) 0.0184(3) Uani 1 1 d . . . . . O2 O 1.2307(3) 0.46262(7) 0.75444(9) 0.0248(3) Uani 1 1 d . . . . . O1 O 1.0945(3) 0.49562(7) 0.61621(10) 0.0300(4) Uani 1 1 d . . . . . H1 H 1.201888 0.526591 0.629003 0.045 Uiso 1 1 calc R U . . . N1 N 0.2536(3) 0.26002(7) 0.64747(10) 0.0164(3) Uani 1 1 d . . . . . H1A H 0.223816 0.238768 0.697362 0.020 Uiso 1 1 calc R U . . . O4 O 1.3234(3) 0.60744(7) 0.63941(10) 0.0296(3) Uani 1 1 d . . . . . H4A H 1.479258 0.629855 0.642578 0.044 Uiso 1 1 d R U . . . H4B H 1.187798 0.635594 0.636398 0.044 Uiso 1 1 d R U . . . C12 C -0.5182(4) 0.09984(8) 0.55088(12) 0.0152(4) Uani 1 1 d . . . . . C9 C -0.1097(4) 0.19536(8) 0.57138(12) 0.0168(4) Uani 1 1 d . . . . . C5 C 0.4660(4) 0.30944(8) 0.65186(12) 0.0155(4) Uani 1 1 d . . . . . C2 C 0.8743(4) 0.40452(8) 0.67239(12) 0.0156(4) Uani 1 1 d . . . . . C6 C 0.6203(4) 0.31548(9) 0.73336(12) 0.0162(4) Uani 1 1 d . . . . . H6 H 0.585808 0.287342 0.781904 0.019 Uiso 1 1 calc R U . . . C7 C 0.8242(4) 0.36285(8) 0.74306(12) 0.0158(4) Uani 1 1 d . . . . . H7 H 0.930906 0.366954 0.798416 0.019 Uiso 1 1 calc R U . . . C1 C 1.0866(4) 0.45640(8) 0.68687(12) 0.0171(4) Uani 1 1 d . . . . . C13 C -0.3730(4) 0.10748(8) 0.63429(12) 0.0167(4) Uani 1 1 d . . . . . H13 H -0.412716 0.080299 0.683450 0.020 Uiso 1 1 calc R U . . . C14 C -0.1716(4) 0.15498(9) 0.64413(12) 0.0188(4) Uani 1 1 d . . . . . H14 H -0.073114 0.160613 0.700649 0.023 Uiso 1 1 calc R U . . . C15 C -0.7735(4) 0.01067(9) 0.60532(12) 0.0186(4) Uani 1 1 d . . . . . H15A H -0.922862 -0.019198 0.585006 0.028 Uiso 1 1 calc R U . . . H15B H -0.836453 0.034313 0.657911 0.028 Uiso 1 1 calc R U . . . H15C H -0.599704 -0.013081 0.621763 0.028 Uiso 1 1 calc R U . . . C8 C 0.1023(4) 0.24421(8) 0.57589(12) 0.0164(4) Uani 1 1 d . . . . . H8 H 0.135341 0.267035 0.522000 0.020 Uiso 1 1 calc R U . . . C11 C -0.4643(4) 0.14058(9) 0.47844(12) 0.0185(4) Uani 1 1 d . . . . . H11 H -0.567821 0.135809 0.422628 0.022 Uiso 1 1 calc R U . . . C10 C -0.2614(4) 0.18732(9) 0.48860(12) 0.0180(4) Uani 1 1 d . . . . . H10 H -0.222995 0.214499 0.439309 0.022 Uiso 1 1 calc R U . . . C4 C 0.5165(4) 0.34961(9) 0.58006(12) 0.0200(4) Uani 1 1 d . . . . . H4 H 0.412965 0.344609 0.524298 0.024 Uiso 1 1 calc R U . . . C3 C 0.7201(4) 0.39722(9) 0.59054(12) 0.0205(4) Uani 1 1 d . . . . . H3 H 0.754958 0.425098 0.541727 0.025 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 Cl1 0.0197(2) 0.0214(2) 0.0133(2) -0.00025(15) 0.00094(15) -0.00155(17) O3 0.0164(6) 0.0199(6) 0.0185(6) 0.0015(5) -0.0028(5) -0.0063(5) O2 0.0229(7) 0.0265(7) 0.0250(7) -0.0043(6) -0.0008(6) -0.0060(6) O1 0.0373(9) 0.0242(7) 0.0282(8) 0.0037(6) -0.0039(6) -0.0141(6) N1 0.0165(8) 0.0171(7) 0.0155(7) -0.0012(6) 0.0008(6) 0.0012(6) O4 0.0282(8) 0.0240(7) 0.0366(9) -0.0023(6) 0.0008(6) -0.0040(6) C12 0.0119(8) 0.0152(8) 0.0184(9) -0.0022(7) 0.0021(7) 0.0001(7) C9 0.0137(9) 0.0144(8) 0.0224(9) -0.0022(7) 0.0031(7) 0.0003(7) C5 0.0124(9) 0.0158(8) 0.0184(9) -0.0049(7) 0.0010(7) 0.0006(7) C2 0.0128(9) 0.0176(8) 0.0164(9) -0.0041(7) 0.0024(7) 0.0006(7) C6 0.0152(9) 0.0182(8) 0.0154(8) -0.0008(7) 0.0014(7) 0.0004(7) C7 0.0137(9) 0.0194(8) 0.0141(8) -0.0032(7) -0.0011(7) -0.0006(7) C1 0.0157(9) 0.0163(8) 0.0195(9) -0.0048(7) 0.0028(7) -0.0010(7) C13 0.0164(9) 0.0172(8) 0.0164(9) 0.0010(7) 0.0002(7) -0.0006(7) C14 0.0184(9) 0.0186(9) 0.0191(9) -0.0021(7) -0.0026(7) 0.0005(7) C15 0.0171(9) 0.0182(9) 0.0202(9) 0.0024(7) -0.0024(7) -0.0050(7) C8 0.0161(9) 0.0170(8) 0.0163(9) -0.0011(7) 0.0011(7) 0.0022(7) C11 0.0181(9) 0.0215(9) 0.0156(9) -0.0004(7) -0.0006(7) -0.0002(7) C10 0.0181(9) 0.0190(9) 0.0172(9) 0.0006(7) 0.0035(7) 0.0007(7) C4 0.0206(10) 0.0236(9) 0.0154(9) -0.0033(7) -0.0038(7) -0.0008(8) C3 0.0236(10) 0.0234(9) 0.0145(9) 0.0018(7) 0.0004(7) -0.0001(8) 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' Cl Cl 0.3639 0.7018 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -3 -2 0 0.1211 3 -1 1 0.1020 0 12 -5 0.0130 0 8 8 0.0064 0 8 -8 0.0055 0 -10 -6 0.0137 0 -14 0 0.0155 0 -7 8 0.0111 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 C12 O3 C15 117.50(13) . . ? C1 O1 H1 109.5 . . ? C5 N1 H1A 117.3 . . ? C8 N1 H1A 117.3 . . ? C8 N1 C5 125.34(16) . . ? H4A O4 H4B 104.6 . . ? O3 C12 C13 123.70(16) . . ? O3 C12 C11 115.55(15) . . ? C13 C12 C11 120.75(16) . . ? C14 C9 C8 123.92(17) . . ? C10 C9 C14 118.94(16) . . ? C10 C9 C8 117.14(16) . . ? C6 C5 N1 116.27(16) . . ? C4 C5 N1 122.81(16) . . ? C4 C5 C6 120.92(17) . . ? C7 C2 C1 118.84(16) . . ? C7 C2 C3 119.24(17) . . ? C3 C2 C1 121.91(17) . . ? C5 C6 H6 120.3 . . ? C7 C6 C5 119.45(17) . . ? C7 C6 H6 120.3 . . ? C2 C7 H7 119.7 . . ? C6 C7 C2 120.55(16) . . ? C6 C7 H7 119.7 . . ? O2 C1 O1 124.06(17) . . ? O2 C1 C2 123.84(17) . . ? O1 C1 C2 112.09(15) . . ? C12 C13 H13 120.5 . . ? C14 C13 C12 119.10(17) . . ? C14 C13 H13 120.5 . . ? C9 C14 H14 119.6 . . ? C13 C14 C9 120.89(17) . . ? C13 C14 H14 119.6 . . ? 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 . . ? N1 C8 C9 125.49(17) . . ? N1 C8 H8 117.3 . . ? C9 C8 H8 117.3 . . ? C12 C11 H11 120.1 . . ? C10 C11 C12 119.71(17) . . ? C10 C11 H11 120.1 . . ? C9 C10 H10 119.7 . . ? C11 C10 C9 120.57(17) . . ? C11 C10 H10 119.7 . . ? C5 C4 H4 120.4 . . ? C5 C4 C3 119.26(16) . . ? C3 C4 H4 120.4 . . ? C2 C3 H3 119.7 . . ? C4 C3 C2 120.56(17) . . ? C4 C3 H3 119.7 . . ? 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 O3 C12 1.350(2) . ? O3 C15 1.433(2) . ? O2 C1 1.196(2) . ? O1 H1 0.8400 . ? O1 C1 1.334(2) . ? N1 H1A 0.8800 . ? N1 C5 1.439(2) . ? N1 C8 1.299(2) . ? O4 H4A 0.8703 . ? O4 H4B 0.8690 . ? C12 C13 1.400(2) . ? C12 C11 1.404(3) . ? C9 C14 1.411(3) . ? C9 C8 1.429(3) . ? C9 C10 1.407(3) . ? C5 C6 1.392(2) . ? C5 C4 1.386(3) . ? C2 C7 1.392(3) . ? C2 C1 1.487(2) . ? C2 C3 1.399(2) . ? C6 H6 0.9500 . ? C6 C7 1.385(3) . ? C7 H7 0.9500 . ? C13 H13 0.9500 . ? C13 C14 1.378(3) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C8 H8 0.9500 . ? C11 H11 0.9500 . ? C11 C10 1.372(3) . ? C10 H10 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.388(3) . ? C3 H3 0.9500 . ? 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 C13 C14 179.41(16) . . . . ? O3 C12 C11 C10 -178.70(16) . . . . ? N1 C5 C6 C7 -178.71(16) . . . . ? N1 C5 C4 C3 178.27(17) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C12 C11 C10 C9 -0.9(3) . . . . ? C5 N1 C8 C9 -179.70(16) . . . . ? C5 C6 C7 C2 0.4(3) . . . . ? C5 C4 C3 C2 0.4(3) . . . . ? C6 C5 C4 C3 -1.3(3) . . . . ? C7 C2 C1 O2 4.4(3) . . . . ? C7 C2 C1 O1 -174.69(16) . . . . ? C7 C2 C3 C4 0.9(3) . . . . ? C1 C2 C7 C6 177.47(16) . . . . ? C1 C2 C3 C4 -177.85(17) . . . . ? C13 C12 C11 C10 1.8(3) . . . . ? C14 C9 C8 N1 -3.8(3) . . . . ? C14 C9 C10 C11 -0.6(3) . . . . ? C15 O3 C12 C13 -2.3(2) . . . . ? C15 O3 C12 C11 178.29(15) . . . . ? C8 N1 C5 C6 -175.10(17) . . . . ? C8 N1 C5 C4 5.3(3) . . . . ? C8 C9 C14 C13 -177.97(17) . . . . ? C8 C9 C10 C11 178.68(17) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C10 C9 C14 C13 1.3(3) . . . . ? C10 C9 C8 N1 176.96(17) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C3 C2 C7 C6 -1.3(3) . . . . ? C3 C2 C1 O2 -176.84(18) . . . . ? C3 C2 C1 O1 4.0(2) . . . . ? 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 -3.0225 -1.7366 -0.2541 0.0889 0.1811 0.9794 2.9952 -0.9379 1.3946 0.0092 0.0254 -0.9996 -0.2263 11.5327 -5.0315 -0.4204 -0.8849 0.2007 0.1352 7.9968 7.7621 -0.9322 0.3294 -0.1503 0.0257 7.7865 -7.8975 -0.0244 -0.9876 0.1554 0.0534 -10.2142 -6.3658 0.9900 -0.1291 0.0572 0.0530 -13.6021 0.1989 0.8217 0.5658 -0.0680 0.0149 -6.5947 8.4188 -0.0779 0.9818 -0.1734