#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:43 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288773 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247580.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_7247580 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, Br, H2 O' _chemical_formula_sum 'C15 H16 Br N O4' _chemical_formula_weight 354.20 _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 2022-12-06 _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 92.616(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.72040(10) _cell_length_b 21.1550(5) _cell_length_c 15.1364(3) _cell_measurement_reflns_used 14065 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 78.7200 _cell_measurement_theta_min 3.5850 _cell_volume 1509.95(6) _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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(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 0.968 _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 -61.00 26.00 0.50 4.55 -- -49.71 19.00 0.00 174 2 \w 27.00 115.00 0.50 4.55 -- 49.71 77.00 -60.00 176 3 \w 98.00 178.00 0.50 16.07 -- 107.75 38.00 30.00 160 4 \w 85.00 173.00 0.50 16.07 -- 107.75 77.00-180.00 176 5 \w 39.00 110.00 0.50 16.07 -- 107.75 -99.00 30.00 142 6 \w 33.00 71.00 0.50 16.07 -- 107.75 -38.00 -60.00 76 7 \w 33.00 71.00 0.50 16.07 -- 107.75 -38.00 -90.00 76 8 \w 39.00 110.00 0.50 16.07 -- 107.75 -99.00 -30.00 142 9 \w 33.00 71.00 0.50 16.07 -- 107.75 -38.00-180.00 76 10 \w 38.00 117.00 0.50 16.07 -- 107.75-125.00 -60.00 158 11 \w 33.00 71.00 0.50 16.07 -- 107.75 -38.00 60.00 76 12 \w 33.00 71.00 0.50 16.07 -- 107.75 -38.00 30.00 76 13 \w 37.00 96.00 0.50 16.07 -- 107.75 -57.00 120.00 118 14 \w 39.00 110.00 0.50 16.07 -- 107.75 -99.00 150.00 142 15 \w 37.00 96.00 0.50 16.07 -- 107.75 -57.00 150.00 118 16 \w 35.00 121.00 0.50 4.55 -- 49.71 57.00 150.00 172 17 \w 59.00 120.00 0.50 4.55 -- 49.71 178.00 150.00 122 18 \w 27.00 115.00 0.50 4.55 -- 49.71 77.00 30.00 176 19 \w 27.00 115.00 0.50 4.55 -- 49.71 77.00-150.00 176 20 \w 35.00 121.00 0.50 4.55 -- 49.71 57.00-150.00 172 21 \w 27.00 115.00 0.50 4.55 -- 49.71 77.00-120.00 176 22 \w 27.00 115.00 0.50 4.55 -- 49.71 77.00 60.00 176 23 \w -92.00 -16.00 0.50 16.07 -- -86.25 125.00 60.00 152 24 \w -97.00 -11.00 0.50 16.07 -- -86.25 19.00-120.00 172 25 \w -124.00 -39.00 0.50 4.55 -- -49.71 -38.00 30.00 170 26 \w -120.00 -38.00 0.50 4.55 -- -49.71-178.00 30.00 164 27 \w -155.00 -82.00 0.50 16.07 -- -86.25 -99.00 150.00 146 28 \w -151.00 -64.00 0.50 16.07 -- -86.25 -77.00 90.00 174 29 \w -151.00 -64.00 0.50 16.07 -- -86.25 -77.00 30.00 174 30 \w -157.00 -85.50 0.50 16.07 -- -86.25 -57.00-150.00 143 ; _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 -0.1307539000 _diffrn_orient_matrix_UB_12 -0.0666901000 _diffrn_orient_matrix_UB_13 -0.0054233000 _diffrn_orient_matrix_UB_21 -0.1478950000 _diffrn_orient_matrix_UB_22 0.0167720000 _diffrn_orient_matrix_UB_23 -0.0898027000 _diffrn_orient_matrix_UB_31 0.2603704000 _diffrn_orient_matrix_UB_32 -0.0239355000 _diffrn_orient_matrix_UB_33 -0.0478263000 _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 0.0516 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 22483 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.882 _diffrn_reflns_theta_min 4.180 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.854 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_correction_T_min 0.466 _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 1.558 _exptl_crystal_description plate _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.367 _exptl_crystal_size_mid 0.054 _exptl_crystal_size_min 0.034 _refine_diff_density_max 1.271 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 3130 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0441 _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^)+(0.0443P)^2^+4.7773P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1075 _refine_ls_wR_factor_ref 0.1102 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2808 _reflns_number_total 3130 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps010-5 _cod_depositor_comments 'Adding full bibliography for 7247579--7247585.cif.' _cod_database_code 7247580 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H16 Br1 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 0.880 _shelx_estimated_absorpt_t_min 0.332 _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), C7(H7), C6(H6), C14(H14), C11(H11), C8(H8), C4(H4), C13(H13), C3(H3), C10(H10) 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 ps010-5_a.res in P2(1)/c ps010-5.res created by SHELXL-2018/3 at 16:27:40 on 06-Dec-2022 REM Old TITL ps010-5 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.096, Rweak 0.018, Alpha 0.037 REM 1.191 for 95 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N3 O2 Br CELL 1.54184 4.7204 21.155 15.1364 90 92.616 90 ZERR 4 0.0001 0.0005 0.0003 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 60 64 4 4 16 L.S. 10 PLAN 20 SIZE 0.034 0.054 0.367 TEMP -173 CONF BOND list 4 fmap 2 53 ACTA MORE -1 BOND $H REM REM REM WGHT 0.044300 4.777300 FVAR 0.36463 BR1 3 -0.838821 0.297339 0.359453 11.00000 0.02733 0.03087 = 0.01371 -0.00045 -0.00006 -0.00370 O3 5 1.720794 0.948579 0.462157 11.00000 0.02117 0.02852 = 0.02397 -0.00017 -0.00335 -0.00604 O2 5 -0.221145 0.543149 0.244409 11.00000 0.03171 0.03670 = 0.03372 -0.00819 -0.00009 -0.00981 O1 5 -0.091883 0.513069 0.382172 11.00000 0.03991 0.03456 = 0.03843 0.00514 -0.00418 -0.01309 AFIX 147 H1 2 -0.210663 0.484063 0.372298 11.00000 -1.50000 AFIX 0 N1 4 0.756288 0.744267 0.346986 11.00000 0.02083 0.02411 = 0.01754 -0.00133 -0.00060 0.00238 AFIX 43 H1A 2 0.783351 0.765694 0.298258 11.00000 -1.20000 AFIX 0 O4 5 -0.344519 0.405154 0.364644 11.00000 0.04280 0.03818 = 0.06097 -0.00300 0.00349 -0.01099 AFIX 3 H4A 2 -0.519789 0.378924 0.367554 11.00000 -1.50000 H4B 2 -0.160889 0.375514 0.365554 11.00000 -1.50000 AFIX 0 C1 1 -0.079151 0.549617 0.310627 11.00000 0.01753 0.02235 = 0.02243 -0.00618 0.00156 -0.00191 C12 1 1.523558 0.903050 0.444675 11.00000 0.01618 0.02149 = 0.02174 -0.00328 -0.00016 0.00099 C7 1 0.186532 0.640989 0.253959 11.00000 0.01821 0.03014 = 0.01623 -0.00539 -0.00280 0.00020 AFIX 43 H7 2 0.081540 0.636059 0.199344 11.00000 -1.20000 AFIX 0 C6 1 0.389502 0.688241 0.262802 11.00000 0.01887 0.02560 = 0.01887 -0.00305 -0.00053 0.00098 AFIX 43 H6 2 0.422946 0.715743 0.214769 11.00000 -1.20000 AFIX 0 C9 1 1.119341 0.808447 0.421764 11.00000 0.01771 0.02067 = 0.02597 -0.00488 0.00485 0.00037 C14 1 1.175868 0.849302 0.351865 11.00000 0.02469 0.02463 = 0.02153 -0.00308 -0.00259 0.00139 AFIX 43 H14 2 1.075640 0.844383 0.296430 11.00000 -1.20000 AFIX 0 C5 1 0.543536 0.694902 0.342810 11.00000 0.01601 0.02307 = 0.02187 -0.00737 -0.00235 0.00161 C11 1 1.473688 0.861730 0.514114 11.00000 0.02262 0.03233 = 0.01761 -0.00193 -0.00307 0.00137 AFIX 43 H11 2 1.578164 0.865918 0.568945 11.00000 -1.20000 AFIX 0 C2 1 0.134973 0.600879 0.323791 11.00000 0.01736 0.02435 = 0.02294 -0.00561 0.00003 0.00162 C8 1 0.909282 0.759242 0.416731 11.00000 0.02111 0.02436 = 0.01905 -0.00225 0.00068 0.00117 AFIX 43 H8 2 0.880623 0.735782 0.469090 11.00000 -1.20000 AFIX 0 C4 1 0.494076 0.656085 0.413605 11.00000 0.02648 0.03011 = 0.01807 -0.00446 -0.00598 0.00029 AFIX 43 H4 2 0.598892 0.661416 0.468176 11.00000 -1.20000 AFIX 0 C13 1 1.375657 0.896605 0.362751 11.00000 0.02254 0.02373 = 0.01810 -0.00046 -0.00097 -0.00157 AFIX 43 H13 2 1.412474 0.924429 0.315364 11.00000 -1.20000 AFIX 0 C3 1 0.288868 0.608976 0.404296 11.00000 0.02813 0.03103 = 0.02078 0.00067 -0.00061 0.00060 AFIX 43 H3 2 0.253029 0.582156 0.452871 11.00000 -1.20000 AFIX 0 C10 1 1.273844 0.815126 0.503076 11.00000 0.02237 0.02776 = 0.01986 0.00055 0.00081 0.00298 AFIX 43 H10 2 1.239224 0.787159 0.550490 11.00000 -1.20000 AFIX 0 C15 1 1.773456 0.992548 0.393804 11.00000 0.01962 0.02502 = 0.02791 -0.00022 -0.00446 -0.00484 AFIX 137 H15A 2 1.841391 0.969944 0.342369 11.00000 -1.50000 H15B 2 1.917570 1.022982 0.415009 11.00000 -1.50000 H15C 2 1.597709 1.015028 0.376913 11.00000 -1.50000 AFIX 0 HKLF 4 REM ps010-5_a.res in P2(1)/c REM wR2 = 0.1102, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0441 for 2808 Fo > 4sig(Fo) and 0.0491 for all 3130 data REM 192 parameters refined using 0 restraints END WGHT 0.0443 4.7793 REM Highest difference peak 1.271, deepest hole -0.489, 1-sigma level 0.094 Q1 1 1.8300 0.9405 0.5412 11.00000 0.05 1.27 Q2 1 -0.7083 0.3188 0.3584 11.00000 0.05 1.08 Q3 1 -0.5457 0.4387 0.3761 11.00000 0.05 1.03 Q4 1 -0.6900 0.2814 0.3621 11.00000 0.05 0.99 Q5 1 -0.8413 0.2410 0.3604 11.00000 0.05 0.45 Q6 1 0.0214 0.5776 0.3194 11.00000 0.05 0.45 Q7 1 1.0450 0.7816 0.4212 11.00000 0.05 0.38 Q8 1 0.7443 0.7231 0.4021 11.00000 0.05 0.38 Q9 1 1.3578 0.8434 0.4991 11.00000 0.05 0.38 Q10 1 0.3044 0.6612 0.2666 11.00000 0.05 0.37 Q11 1 0.4346 0.6238 0.4224 11.00000 0.05 0.35 Q12 1 0.3884 0.6366 0.4255 11.00000 0.05 0.35 Q13 1 0.4848 0.6813 0.3767 11.00000 0.05 0.34 Q14 1 -0.8704 0.3572 0.3431 11.00000 0.05 0.34 Q15 1 1.2407 0.8797 0.3669 11.00000 0.05 0.34 Q16 1 0.6541 0.7009 0.3498 11.00000 0.05 0.32 Q17 1 -1.0979 0.3014 0.3755 11.00000 0.05 0.31 Q18 1 -0.1653 0.5586 0.3001 11.00000 0.05 0.30 Q19 1 0.8901 0.7711 0.3543 11.00000 0.05 0.29 Q20 1 -0.7538 0.2610 0.4151 11.00000 0.05 0.29 ; _shelx_res_checksum 97351 _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 1.993 _oxdiff_exptl_absorpt_empirical_full_min 0.432 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 Br1 Br -0.83882(7) 0.29734(2) 0.35945(2) 0.02400(13) Uani 1 1 d . . . . . O3 O 1.7208(5) 0.94858(11) 0.46216(16) 0.0247(5) Uani 1 1 d . . . . . O2 O -0.2211(6) 0.54315(13) 0.24441(18) 0.0341(6) Uani 1 1 d . . . . . O1 O -0.0919(6) 0.51307(13) 0.38217(19) 0.0378(6) Uani 1 1 d . . . . . H1 H -0.210663 0.484063 0.372298 0.057 Uiso 1 1 calc R U . . . N1 N 0.7563(6) 0.74427(13) 0.34699(18) 0.0209(6) Uani 1 1 d . . . . . H1A H 0.783351 0.765694 0.298258 0.025 Uiso 1 1 calc R U . . . O4 O -0.3445(7) 0.40515(15) 0.3646(2) 0.0473(8) Uani 1 1 d . . . . . H4A H -0.519789 0.378924 0.367554 0.071 Uiso 1 1 d R U . . . H4B H -0.160889 0.375514 0.365554 0.071 Uiso 1 1 d R U . . . C1 C -0.0792(7) 0.54962(15) 0.3106(2) 0.0208(6) Uani 1 1 d . . . . . C12 C 1.5236(6) 0.90305(15) 0.4447(2) 0.0198(6) Uani 1 1 d . . . . . C7 C 0.1865(7) 0.64099(16) 0.2540(2) 0.0216(6) Uani 1 1 d . . . . . H7 H 0.081540 0.636059 0.199344 0.026 Uiso 1 1 calc R U . . . C6 C 0.3895(7) 0.68824(16) 0.2628(2) 0.0212(6) Uani 1 1 d . . . . . H6 H 0.422946 0.715743 0.214769 0.025 Uiso 1 1 calc R U . . . C9 C 1.1193(7) 0.80845(15) 0.4218(2) 0.0213(7) Uani 1 1 d . . . . . C14 C 1.1759(7) 0.84930(16) 0.3519(2) 0.0237(7) Uani 1 1 d . . . . . H14 H 1.075640 0.844383 0.296430 0.028 Uiso 1 1 calc R U . . . C5 C 0.5435(7) 0.69490(15) 0.3428(2) 0.0204(6) Uani 1 1 d . . . . . C11 C 1.4737(7) 0.86173(17) 0.5141(2) 0.0243(7) Uani 1 1 d . . . . . H11 H 1.578164 0.865918 0.568945 0.029 Uiso 1 1 calc R U . . . C2 C 0.1350(7) 0.60088(16) 0.3238(2) 0.0216(7) Uani 1 1 d . . . . . C8 C 0.9093(7) 0.75924(16) 0.4167(2) 0.0215(6) Uani 1 1 d . . . . . H8 H 0.880623 0.735782 0.469090 0.026 Uiso 1 1 calc R U . . . C4 C 0.4941(7) 0.65608(17) 0.4136(2) 0.0251(7) Uani 1 1 d . . . . . H4 H 0.598892 0.661416 0.468176 0.030 Uiso 1 1 calc R U . . . C13 C 1.3757(7) 0.89661(16) 0.3628(2) 0.0215(6) Uani 1 1 d . . . . . H13 H 1.412474 0.924429 0.315364 0.026 Uiso 1 1 calc R U . . . C3 C 0.2889(7) 0.60898(18) 0.4043(2) 0.0267(7) Uani 1 1 d . . . . . H3 H 0.253029 0.582156 0.452871 0.032 Uiso 1 1 calc R U . . . C10 C 1.2738(7) 0.81513(16) 0.5031(2) 0.0233(7) Uani 1 1 d . . . . . H10 H 1.239224 0.787159 0.550490 0.028 Uiso 1 1 calc R U . . . C15 C 1.7735(7) 0.99255(16) 0.3938(2) 0.0243(7) Uani 1 1 d . . . . . H15A H 1.841391 0.969944 0.342369 0.037 Uiso 1 1 calc R U . . . H15B H 1.917570 1.022982 0.415009 0.037 Uiso 1 1 calc R U . . . H15C H 1.597709 1.015028 0.376913 0.037 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 Br1 0.0273(2) 0.0309(2) 0.01371(18) -0.00045(13) -0.00006(12) -0.00370(14) O3 0.0212(11) 0.0285(12) 0.0240(12) -0.0002(10) -0.0033(9) -0.0060(9) O2 0.0317(14) 0.0367(15) 0.0337(14) -0.0082(11) -0.0001(11) -0.0098(11) O1 0.0399(16) 0.0346(15) 0.0384(15) 0.0051(12) -0.0042(12) -0.0131(12) N1 0.0208(13) 0.0241(14) 0.0175(13) -0.0013(11) -0.0006(10) 0.0024(11) O4 0.0428(17) 0.0382(16) 0.061(2) -0.0030(15) 0.0035(15) -0.0110(13) C1 0.0175(15) 0.0224(16) 0.0224(16) -0.0062(13) 0.0016(12) -0.0019(12) C12 0.0162(15) 0.0215(15) 0.0217(16) -0.0033(12) -0.0002(12) 0.0010(12) C7 0.0182(15) 0.0301(17) 0.0162(15) -0.0054(13) -0.0028(12) 0.0002(13) C6 0.0189(15) 0.0256(17) 0.0189(15) -0.0031(12) -0.0005(12) 0.0010(12) C9 0.0177(15) 0.0207(16) 0.0260(17) -0.0049(13) 0.0048(12) 0.0004(12) C14 0.0247(17) 0.0246(16) 0.0215(16) -0.0031(13) -0.0026(13) 0.0014(13) C5 0.0160(14) 0.0231(16) 0.0219(16) -0.0074(12) -0.0024(12) 0.0016(12) C11 0.0226(16) 0.0323(18) 0.0176(16) -0.0019(13) -0.0031(12) 0.0014(13) C2 0.0174(15) 0.0244(16) 0.0229(16) -0.0056(13) 0.0000(12) 0.0016(12) C8 0.0211(15) 0.0244(16) 0.0191(15) -0.0023(12) 0.0007(12) 0.0012(12) C4 0.0265(17) 0.0301(18) 0.0181(16) -0.0045(13) -0.0060(13) 0.0003(14) C13 0.0225(16) 0.0237(16) 0.0181(15) -0.0005(12) -0.0010(12) -0.0016(12) C3 0.0281(18) 0.0310(18) 0.0208(16) 0.0007(14) -0.0006(13) 0.0006(14) C10 0.0224(16) 0.0278(17) 0.0199(16) 0.0006(13) 0.0008(12) 0.0030(13) C15 0.0196(15) 0.0250(17) 0.0279(17) -0.0002(13) -0.0045(13) -0.0048(12) 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' Br Br -0.6763 1.2805 '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 0 10 6 0.0172 0 -10 -6 0.0172 3 3 -1 0.1634 -3 -1 2 0.1764 -3 0 5 0.1544 0 -13 -4 0.0143 0 -12 -5 0.0130 0 8 8 0.0197 0 0 -10 0.0241 0 13 3 0.0193 0 -2 10 0.0196 0 10 -6 0.0295 0 11 -6 0.0247 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 117.6(2) . . ? C1 O1 H1 109.5 . . ? C5 N1 H1A 117.5 . . ? C8 N1 H1A 117.5 . . ? C8 N1 C5 125.0(3) . . ? H4A O4 H4B 110.3 . . ? O2 C1 O1 125.0(3) . . ? O2 C1 C2 123.4(3) . . ? O1 C1 C2 111.6(3) . . ? O3 C12 C11 115.8(3) . . ? O3 C12 C13 123.4(3) . . ? C11 C12 C13 120.7(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C2 C7 C6 120.8(3) . . ? C7 C6 H6 120.4 . . ? C7 C6 C5 119.2(3) . . ? C5 C6 H6 120.4 . . ? C14 C9 C8 124.2(3) . . ? C14 C9 C10 119.3(3) . . ? C10 C9 C8 116.6(3) . . ? C9 C14 H14 119.7 . . ? C13 C14 C9 120.7(3) . . ? C13 C14 H14 119.7 . . ? C6 C5 N1 116.4(3) . . ? C4 C5 N1 122.5(3) . . ? C4 C5 C6 121.1(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 120.1 . . ? C7 C2 C1 119.0(3) . . ? C7 C2 C3 119.1(3) . . ? C3 C2 C1 121.8(3) . . ? N1 C8 C9 125.4(3) . . ? N1 C8 H8 117.3 . . ? C9 C8 H8 117.3 . . ? C5 C4 H4 120.3 . . ? C5 C4 C3 119.3(3) . . ? C3 C4 H4 120.3 . . ? C12 C13 H13 120.5 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.5 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C9 C10 H10 119.8 . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.8 . . ? 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 O3 C12 1.357(4) . ? O3 C15 1.422(4) . ? O2 C1 1.188(4) . ? O1 H1 0.8400 . ? O1 C1 1.334(4) . ? N1 H1A 0.8800 . ? N1 C5 1.448(4) . ? N1 C8 1.291(4) . ? O4 H4A 0.9988 . ? O4 H4B 1.0694 . ? C1 C2 1.490(4) . ? C12 C11 1.395(5) . ? C12 C13 1.402(4) . ? C7 H7 0.9500 . ? C7 C6 1.387(5) . ? C7 C2 1.386(5) . ? C6 H6 0.9500 . ? C6 C5 1.391(4) . ? C9 C14 1.401(5) . ? C9 C8 1.437(5) . ? C9 C10 1.409(5) . ? C14 H14 0.9500 . ? C14 C13 1.380(5) . ? C5 C4 1.378(5) . ? C11 H11 0.9500 . ? C11 C10 1.369(5) . ? C2 C3 1.400(5) . ? C8 H8 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.392(5) . ? C13 H13 0.9500 . ? C3 H3 0.9500 . ? 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 178.6(3) . . . . ? O3 C12 C13 C14 -179.0(3) . . . . ? O2 C1 C2 C7 -4.3(5) . . . . ? O2 C1 C2 C3 176.8(3) . . . . ? O1 C1 C2 C7 176.4(3) . . . . ? O1 C1 C2 C3 -2.5(5) . . . . ? N1 C5 C4 C3 -179.0(3) . . . . ? C1 C2 C3 C4 177.9(3) . . . . ? C12 C11 C10 C9 0.4(5) . . . . ? C7 C6 C5 N1 178.7(3) . . . . ? C7 C6 C5 C4 -1.1(5) . . . . ? C7 C2 C3 C4 -1.0(5) . . . . ? C6 C7 C2 C1 -178.3(3) . . . . ? C6 C7 C2 C3 0.7(5) . . . . ? C6 C5 C4 C3 0.8(5) . . . . ? C9 C14 C13 C12 0.5(5) . . . . ? C14 C9 C8 N1 3.5(5) . . . . ? C14 C9 C10 C11 1.1(5) . . . . ? C5 N1 C8 C9 -179.5(3) . . . . ? C5 C4 C3 C2 0.3(5) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C2 C7 C6 C5 0.4(5) . . . . ? C8 N1 C5 C6 176.5(3) . . . . ? C8 N1 C5 C4 -3.6(5) . . . . ? C8 C9 C14 C13 178.1(3) . . . . ? C8 C9 C10 C11 -178.6(3) . . . . ? C13 C12 C11 C10 -1.4(5) . . . . ? C10 C9 C14 C13 -1.5(5) . . . . ? C10 C9 C8 N1 -176.8(3) . . . . ? C15 O3 C12 C11 -178.6(3) . . . . ? C15 O3 C12 C13 1.4(5) . . . . ? 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 0.0613 10.4787 6.3319 -0.7412 -0.4019 -0.5377 -0.0613 -10.4787 -6.3319 0.7412 0.4019 0.5377 2.9930 2.8698 -0.8681 -0.5780 -0.3166 0.7521 -3.0186 -1.3227 1.8332 0.4730 0.2596 -0.8420 -2.7104 0.1297 4.9765 0.3188 -0.0439 -0.9468 -0.1832 -12.5658 -3.8890 0.8831 0.1656 0.4391 -0.3630 -12.0187 -4.5500 0.8737 0.2607 0.4108 0.0402 7.8064 8.0677 -0.5696 -0.5995 -0.5622 0.1333 0.1927 -9.8241 0.0230 0.8657 0.5000 0.4385 13.0831 2.5670 -0.9438 -0.0759 -0.3218 -0.1167 -1.6392 9.7546 0.0717 -0.8862 -0.4577 0.4254 10.4160 -6.3127 -0.7160 0.6787 0.1634 0.2239 10.8935 -5.9668 -0.7234 0.6854 0.0829