#------------------------------------------------------------------------------ #$Date: 2020-04-22 05:33:06 +0300 (Wed, 22 Apr 2020) $ #$Revision: 251004 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240372.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_7240372 loop_ _publ_author_name 'Popa, Marcel Mirel' 'Shova, Sergiu' 'Hrubaru, Madalina' 'Barbu, Loredana' 'Draghici, Constantin' 'Dumitrascu, Florea' 'Dumitrescu, Denisa E.' _publ_section_title ; Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition ; _journal_issue 27 _journal_name_full 'RSC Advances' _journal_page_first 15656 _journal_paper_doi 10.1039/D0RA02368J _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C16 H17 Br N2 O4' _chemical_formula_sum 'C16 H17 Br N2 O4' _chemical_formula_weight 381.22 _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 direct _audit_creation_date 2018-06-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-06-14 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.285(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.1295(6) _cell_length_b 12.3462(8) _cell_length_c 16.9591(7) _cell_measurement_reflns_used 3108 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.3450 _cell_measurement_theta_min 3.7350 _cell_volume 1684.39(18) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0851 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 6.00 35.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 57.0000 30.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega -37.00 2.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -19.2884 -57.0000 150.0000 39 #__ type_ start__ end____ width___ exp.time_ 3 omega -52.00 93.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 0.0000 0.0000 145 #__ type_ start__ end____ width___ exp.time_ 4 omega 48.00 89.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -178.0000 -90.0000 41 #__ type_ start__ end____ width___ exp.time_ 5 omega 70.00 96.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -178.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega -48.00 37.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -37.0000 -60.0000 85 #__ type_ start__ end____ width___ exp.time_ 7 omega -87.00 -11.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -19.2884 -57.0000 -120.0000 76 #__ type_ start__ end____ width___ exp.time_ 8 omega 59.00 84.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 178.0000 -180.0000 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0375702000 _diffrn_orient_matrix_UB_12 -0.0313457000 _diffrn_orient_matrix_UB_13 -0.0275636000 _diffrn_orient_matrix_UB_21 0.0795473000 _diffrn_orient_matrix_UB_22 0.0182494000 _diffrn_orient_matrix_UB_23 0.0177274000 _diffrn_orient_matrix_UB_31 0.0061273000 _diffrn_orient_matrix_UB_32 -0.0445521000 _diffrn_orient_matrix_UB_33 0.0266809000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_unetI/netI 0.0381 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 12209 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.025 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_min 3.118 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.461 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.403 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2969 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0436P)^2^+0.4160P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.0955 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2287 _reflns_number_total 2969 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL shC_545_FlDu in P21/c #14 shc_545_fldu.res created by SHELXL-2018/3 at 11:53:41 on 14-Jun-2018 REM reset to P21/c #14 CELL 0.71073 8.12955 12.34625 16.95911 90 98.2848 90 ZERR 4 0.00055 0.00079 0.00071 0 0.0051 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 64 68 4 8 16 EQIV $1 1-X,-0.5+Y,1.5-Z EQIV $2 +X,1.5-Y,-0.5+Z L.S. 15 PLAN 20 SIZE 0.15 0.15 0.2 HTAB C12 O15_$1 HTAB C2 O15_$2 BOND fmap 2 acta SHEL 99 0.84 OMIT 2 1 2 OMIT -3 6 3 OMIT -2 4 3 REM REM REM WGHT 0.043600 0.416000 FVAR 6.27856 BR1 3 0.184467 0.597957 0.272267 11.00000 0.07628 0.08282 = 0.03229 -0.01451 0.00500 -0.01304 O13 5 0.779644 0.978323 0.660397 11.00000 0.05961 0.03693 = 0.04661 0.00145 0.01894 -0.01250 O15 5 0.721082 0.957656 0.784362 11.00000 0.05419 0.04241 = 0.04162 -0.00850 0.01646 -0.01041 O17 5 0.580645 0.615829 0.837790 11.00000 0.06316 0.04861 = 0.03620 0.01146 -0.00326 -0.01849 O19 5 0.793531 0.733140 0.854283 11.00000 0.04559 0.05857 = 0.04782 0.01035 -0.01465 -0.01182 N1 4 0.496030 0.715719 0.606713 11.00000 0.03039 0.03286 = 0.03124 -0.00049 0.00101 -0.00283 N2 4 0.571111 0.814279 0.612558 11.00000 0.03329 0.02997 = 0.03863 0.00030 0.00594 -0.00265 C1 1 0.278303 0.627255 0.379207 11.00000 0.04840 0.03837 = 0.02885 -0.00378 0.00656 -0.00674 C2 1 0.447136 0.623764 0.398551 11.00000 0.04499 0.04776 = 0.04010 -0.00900 0.01766 -0.00297 AFIX 43 H2 2 0.514125 0.603597 0.360966 11.00000 -1.20000 AFIX 0 C3 1 0.516044 0.650826 0.475087 11.00000 0.03021 0.04755 = 0.04894 -0.00554 0.00776 -0.00003 AFIX 43 H3 2 0.630744 0.648945 0.489716 11.00000 -1.20000 AFIX 0 C4 1 0.414578 0.680694 0.529925 11.00000 0.03302 0.03065 = 0.03138 0.00146 0.00307 -0.00172 C5 1 0.242819 0.682749 0.511499 11.00000 0.03166 0.04737 = 0.02977 0.00122 0.00304 0.00347 C6 1 0.176041 0.655457 0.433518 11.00000 0.03363 0.05497 = 0.03345 -0.00150 0.00110 -0.00178 AFIX 43 H6 2 0.061474 0.656411 0.418311 11.00000 -1.20000 AFIX 0 C7 1 0.130137 0.717888 0.570891 11.00000 0.03470 0.09840 = 0.02977 -0.01100 0.00154 0.01316 AFIX 13 H7 2 0.199497 0.731203 0.622188 11.00000 -1.20000 AFIX 0 C8 1 0.041400 0.823582 0.543558 11.00000 0.07771 0.09352 = 0.07875 -0.02236 0.02189 0.02657 AFIX 137 H8A 2 -0.018805 0.849574 0.584463 11.00000 -1.50000 H8B 2 -0.034605 0.810748 0.495680 11.00000 -1.50000 H8C 2 0.121941 0.876729 0.533385 11.00000 -1.50000 AFIX 0 C9 1 0.004963 0.629732 0.582841 11.00000 0.06104 0.12841 = 0.07532 0.02191 0.03694 0.00843 AFIX 137 H9A 2 -0.058155 0.651498 0.623833 11.00000 -1.50000 H9B 2 0.062870 0.563576 0.598251 11.00000 -1.50000 H9C 2 -0.068709 0.618569 0.533968 11.00000 -1.50000 AFIX 0 C10 1 0.640550 0.821081 0.688386 11.00000 0.02572 0.03095 = 0.03194 -0.00127 0.00661 0.00183 C11 1 0.610622 0.726693 0.731343 11.00000 0.02978 0.03054 = 0.03251 0.00141 0.00319 0.00094 C12 1 0.516887 0.662164 0.676204 11.00000 0.03578 0.03005 = 0.03835 0.00292 0.00434 -0.00225 AFIX 43 H12 2 0.475445 0.593815 0.685376 11.00000 -1.20000 AFIX 0 C13 1 0.674115 0.695151 0.814016 11.00000 0.03861 0.03058 = 0.03676 -0.00179 0.00335 0.00108 C14 1 0.633771 0.572548 0.916154 11.00000 0.10414 0.05332 = 0.04504 0.01941 -0.00976 -0.02168 AFIX 137 H14A 2 0.745644 0.546216 0.919336 11.00000 -1.50000 H14B 2 0.561675 0.514135 0.926220 11.00000 -1.50000 H14C 2 0.629419 0.628433 0.955158 11.00000 -1.50000 AFIX 0 C15 1 0.719183 0.924616 0.717971 11.00000 0.02826 0.03291 = 0.03882 0.00135 0.00864 0.00028 C16 1 0.842204 1.086099 0.680474 11.00000 0.07127 0.03638 = 0.07535 0.00510 0.01989 -0.01691 AFIX 137 H16A 2 0.886717 1.116465 0.635906 11.00000 -1.50000 H16B 2 0.928099 1.082313 0.725606 11.00000 -1.50000 H16C 2 0.753286 1.130996 0.693224 11.00000 -1.50000 AFIX 0 HKLF 4 REM shC_545_FlDu in P21/c #14 REM wR2 = 0.0955, GooF = S = 1.058, Restrained GooF = 1.058 for all data REM R1 = 0.0387 for 2287 Fo > 4sig(Fo) and 0.0592 for all 2969 data REM 212 parameters refined using 0 restraints END WGHT 0.0436 0.4160 REM Highest difference peak 0.403, deepest hole -0.579, 1-sigma level 0.062 Q1 1 0.1657 0.5369 0.3009 11.00000 0.05 0.40 Q2 1 0.5237 0.7637 0.7777 11.00000 0.05 0.20 Q3 1 0.3181 0.7216 0.3298 11.00000 0.05 0.19 Q4 1 0.5000 0.7980 0.7838 11.00000 0.05 0.19 Q5 1 1.0094 1.0828 0.6797 11.00000 0.05 0.19 Q6 1 1.1021 1.0231 0.6983 11.00000 0.05 0.19 Q7 1 0.5041 0.6468 0.3253 11.00000 0.05 0.19 Q8 1 0.6865 0.4505 0.9965 11.00000 0.05 0.18 Q9 1 0.4403 0.6100 0.2701 11.00000 0.05 0.18 Q10 1 0.0531 0.6066 0.4114 11.00000 0.05 0.17 Q11 1 0.4955 0.8448 0.7390 11.00000 0.05 0.17 Q12 1 0.4046 0.7329 0.3097 11.00000 0.05 0.17 Q13 1 0.2742 0.8199 0.6811 11.00000 0.05 0.17 Q14 1 0.6553 0.4807 0.8942 11.00000 0.05 0.17 Q15 1 0.2419 0.4817 0.3628 11.00000 0.05 0.17 Q16 1 0.6608 0.7004 0.7611 11.00000 0.05 0.17 Q17 1 0.6301 0.4764 0.9258 11.00000 0.05 0.17 Q18 1 0.1902 0.6735 0.5453 11.00000 0.05 0.17 Q19 1 0.7434 0.5989 0.9470 11.00000 0.05 0.17 Q20 1 1.0892 1.0987 0.6877 11.00000 0.05 0.16 REM The information below was added by Olex2. REM REM R1 = 0.0387 for 2287 Fo > 4sig(Fo) and 0.0592 for all 14998 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.40, deepest hole -0.58 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0592 REM R1_gt = 0.0387 REM wR_ref = 0.0955 REM GOOF = 1.058 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 14998 REM Reflections_gt = 2287 REM Parameters = n/a REM Hole = -0.58 REM Peak = 0.40 REM Flack = n/a ; _cod_data_source_file d0ra02368j2.cif _cod_data_source_block shc_545_fldu _cod_original_cell_volume 1684.41(17) _cod_database_code 7240372 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C20H20N4O2Cl1 _chemical_oxdiff_usercomment I_479 _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 0.709 _shelx_estimated_absorpt_t_min 0.639 _reflns_odcompleteness_completeness 99.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), C12(H12) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C) ; _olex2_submission_special_instructions 'No special instructions were received' 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 0.18447(5) 0.59796(3) 0.27227(2) 0.06407(17) Uani 1 1 d . . . . . O13 O 0.7796(3) 0.97832(15) 0.66040(11) 0.0466(5) Uani 1 1 d . . . . . O15 O 0.7211(3) 0.95766(16) 0.78436(11) 0.0451(5) Uani 1 1 d . . . . . O17 O 0.5806(3) 0.61583(16) 0.83779(12) 0.0503(6) Uani 1 1 d . . . . . O19 O 0.7935(3) 0.73314(17) 0.85428(12) 0.0528(6) Uani 1 1 d . . . . . N1 N 0.4960(3) 0.71572(17) 0.60671(12) 0.0318(5) Uani 1 1 d . . . . . N2 N 0.5711(3) 0.81428(17) 0.61256(13) 0.0339(5) Uani 1 1 d . . . . . C1 C 0.2783(4) 0.6273(2) 0.37921(16) 0.0384(7) Uani 1 1 d . . . . . C2 C 0.4471(4) 0.6238(2) 0.39855(17) 0.0432(7) Uani 1 1 d . . . . . H2 H 0.514125 0.603597 0.360966 0.052 Uiso 1 1 calc R . . . . C3 C 0.5160(4) 0.6508(2) 0.47509(17) 0.0420(7) Uani 1 1 d . . . . . H3 H 0.630744 0.648945 0.489716 0.050 Uiso 1 1 calc R . . . . C4 C 0.4146(3) 0.6807(2) 0.52992(14) 0.0318(6) Uani 1 1 d . . . . . C5 C 0.2428(4) 0.6827(2) 0.51150(15) 0.0364(7) Uani 1 1 d . . . . . C6 C 0.1760(4) 0.6555(2) 0.43352(15) 0.0411(7) Uani 1 1 d . . . . . H6 H 0.061474 0.656411 0.418311 0.049 Uiso 1 1 calc R . . . . C7 C 0.1301(4) 0.7179(3) 0.57089(17) 0.0546(9) Uani 1 1 d . . . . . H7 H 0.199497 0.731203 0.622188 0.066 Uiso 1 1 calc R . . . . C8 C 0.0414(6) 0.8236(3) 0.5436(2) 0.0823(13) Uani 1 1 d . . . . . H8A H -0.018805 0.849574 0.584463 0.123 Uiso 1 1 calc GR . . . . H8B H -0.034605 0.810748 0.495680 0.123 Uiso 1 1 calc GR . . . . H8C H 0.121941 0.876729 0.533385 0.123 Uiso 1 1 calc GR . . . . C9 C 0.0050(5) 0.6297(4) 0.5828(2) 0.0856(13) Uani 1 1 d . . . . . H9A H -0.058155 0.651498 0.623833 0.128 Uiso 1 1 calc GR . . . . H9B H 0.062870 0.563576 0.598251 0.128 Uiso 1 1 calc GR . . . . H9C H -0.068709 0.618569 0.533968 0.128 Uiso 1 1 calc GR . . . . C10 C 0.6406(3) 0.8211(2) 0.68839(15) 0.0293(6) Uani 1 1 d . . . . . C11 C 0.6106(3) 0.7267(2) 0.73134(15) 0.0311(6) Uani 1 1 d . . . . . C12 C 0.5169(3) 0.6622(2) 0.67620(15) 0.0348(6) Uani 1 1 d . . . . . H12 H 0.475445 0.593815 0.685376 0.042 Uiso 1 1 calc R . . . . C13 C 0.6741(4) 0.6952(2) 0.81402(16) 0.0355(6) Uani 1 1 d . . . . . C14 C 0.6338(5) 0.5725(3) 0.91615(19) 0.0695(12) Uani 1 1 d . . . . . H14A H 0.745644 0.546216 0.919336 0.104 Uiso 1 1 calc GR . . . . H14B H 0.561675 0.514135 0.926220 0.104 Uiso 1 1 calc GR . . . . H14C H 0.629419 0.628433 0.955158 0.104 Uiso 1 1 calc GR . . . . C15 C 0.7192(3) 0.9246(2) 0.71797(17) 0.0330(6) Uani 1 1 d . . . . . C16 C 0.8422(5) 1.0861(2) 0.6805(2) 0.0601(10) Uani 1 1 d . . . . . H16A H 0.886717 1.116465 0.635906 0.090 Uiso 1 1 calc GR . . . . H16B H 0.928099 1.082313 0.725606 0.090 Uiso 1 1 calc GR . . . . H16C H 0.753286 1.130996 0.693224 0.090 Uiso 1 1 calc GR . . . . 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 0.0763(3) 0.0828(3) 0.0323(2) -0.01451(16) 0.00500(16) -0.0130(2) O13 0.0596(15) 0.0369(12) 0.0466(12) 0.0014(9) 0.0189(10) -0.0125(10) O15 0.0542(14) 0.0424(12) 0.0416(12) -0.0085(9) 0.0165(10) -0.0104(10) O17 0.0632(15) 0.0486(13) 0.0362(11) 0.0115(9) -0.0033(10) -0.0185(11) O19 0.0456(14) 0.0586(14) 0.0478(12) 0.0104(10) -0.0146(11) -0.0118(11) N1 0.0304(13) 0.0329(12) 0.0312(12) -0.0005(10) 0.0010(9) -0.0028(10) N2 0.0333(14) 0.0300(12) 0.0386(13) 0.0003(10) 0.0059(10) -0.0027(10) C1 0.0484(19) 0.0384(16) 0.0288(14) -0.0038(12) 0.0066(13) -0.0067(14) C2 0.045(2) 0.0478(18) 0.0401(17) -0.0090(14) 0.0177(14) -0.0030(14) C3 0.0302(16) 0.0475(18) 0.0489(18) -0.0055(14) 0.0078(14) 0.0000(13) C4 0.0330(16) 0.0307(14) 0.0314(14) 0.0015(12) 0.0031(12) -0.0017(12) C5 0.0317(16) 0.0474(17) 0.0298(14) 0.0012(13) 0.0030(12) 0.0035(13) C6 0.0336(17) 0.0550(19) 0.0335(15) -0.0015(14) 0.0011(13) -0.0018(14) C7 0.0347(19) 0.098(3) 0.0298(15) -0.0110(17) 0.0015(13) 0.0132(18) C8 0.078(3) 0.094(3) 0.079(3) -0.022(2) 0.022(2) 0.027(2) C9 0.061(3) 0.128(4) 0.075(3) 0.022(2) 0.037(2) 0.008(3) C10 0.0257(14) 0.0310(15) 0.0319(14) -0.0013(11) 0.0066(11) 0.0018(11) C11 0.0298(15) 0.0305(14) 0.0325(14) 0.0014(12) 0.0032(12) 0.0009(12) C12 0.0358(16) 0.0300(15) 0.0383(15) 0.0029(12) 0.0043(13) -0.0022(12) C13 0.0386(18) 0.0306(15) 0.0368(15) -0.0018(13) 0.0033(13) 0.0011(13) C14 0.104(3) 0.053(2) 0.045(2) 0.0194(16) -0.010(2) -0.022(2) C15 0.0283(16) 0.0329(15) 0.0388(16) 0.0013(13) 0.0086(12) 0.0003(12) C16 0.071(3) 0.0364(18) 0.075(2) 0.0051(16) 0.020(2) -0.0169(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C15 O13 C16 116.1(2) . . ? C13 O17 C14 116.3(2) . . ? N2 N1 C4 118.6(2) . . ? C12 N1 N2 112.3(2) . . ? C12 N1 C4 129.1(2) . . ? C10 N2 N1 104.52(19) . . ? C2 C1 Br1 118.4(2) . . ? C2 C1 C6 122.2(3) . . ? C6 C1 Br1 119.4(2) . . ? C1 C2 C3 118.5(3) . . ? C2 C3 C4 119.9(3) . . ? C3 C4 N1 116.6(2) . . ? C3 C4 C5 122.3(2) . . ? C5 C4 N1 121.0(2) . . ? C4 C5 C6 116.8(2) . . ? C4 C5 C7 122.7(2) . . ? C6 C5 C7 120.5(3) . . ? C1 C6 C5 120.4(3) . . ? C5 C7 C8 110.2(3) . . ? C5 C7 C9 111.2(3) . . ? C9 C7 C8 110.8(3) . . ? N2 C10 C11 111.4(2) . . ? N2 C10 C15 118.9(2) . . ? C11 C10 C15 129.3(2) . . ? C10 C11 C13 130.2(2) . . ? C12 C11 C10 104.3(2) . . ? C12 C11 C13 125.3(2) . . ? N1 C12 C11 107.5(2) . . ? O17 C13 C11 110.1(2) . . ? O19 C13 O17 124.3(3) . . ? O19 C13 C11 125.6(3) . . ? O13 C15 C10 111.6(2) . . ? O15 C15 O13 124.4(3) . . ? O15 C15 C10 124.0(2) . . ? 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 Br1 C1 1.898(3) . ? O13 C15 1.332(3) . ? O13 C16 1.447(3) . ? O15 C15 1.196(3) . ? O17 C13 1.337(3) . ? O17 C14 1.440(4) . ? O19 C13 1.199(3) . ? N1 N2 1.359(3) . ? N1 C4 1.440(3) . ? N1 C12 1.341(3) . ? N2 C10 1.331(3) . ? C1 C2 1.365(4) . ? C1 C6 1.372(4) . ? C2 C3 1.379(4) . ? C3 C4 1.379(4) . ? C4 C5 1.386(4) . ? C5 C6 1.397(4) . ? C5 C7 1.519(4) . ? C7 C8 1.530(5) . ? C7 C9 1.523(5) . ? C10 C11 1.414(3) . ? C10 C15 1.484(4) . ? C11 C12 1.373(4) . ? C11 C13 1.475(4) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2 H2 O15 0.93 2.39 3.311(3) 169.8 4_575 yes C12 H12 O15 0.93 2.42 3.307(3) 158.5 2_646 yes