#------------------------------------------------------------------------------ #$Date: 2020-04-22 05:33:06 +0300 (Wed, 22 Apr 2020) $ #$Revision: 251004 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240370.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_7240370 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 'C11 H12 Br2 N2 O3' _chemical_formula_sum 'C11 H12 Br2 N2 O3' _chemical_formula_weight 380.05 _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 2018-06-13 _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 99.867(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6989(11) _cell_length_b 10.7694(15) _cell_length_c 15.0669(17) _cell_measurement_reflns_used 1935 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.6210 _cell_measurement_theta_min 3.4930 _cell_volume 1390.6(3) _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 -36.00 -10.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -19.2884 -57.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -6.00 56.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -99.0000 90.0000 62 #__ type_ start__ end____ width___ exp.time_ 3 omega -49.00 41.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -57.0000 -30.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 36.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -57.0000 -150.0000 85 #__ type_ start__ end____ width___ exp.time_ 5 omega -8.00 25.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 77.0000 -30.0000 33 #__ type_ start__ end____ width___ exp.time_ 6 omega -12.00 26.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 77.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 7 omega 37.00 63.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 178.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -49.00 29.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -57.0000 90.0000 78 ; _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 -0.0707858000 _diffrn_orient_matrix_UB_12 0.0254834000 _diffrn_orient_matrix_UB_13 -0.0231914000 _diffrn_orient_matrix_UB_21 0.0408293000 _diffrn_orient_matrix_UB_22 0.0271026000 _diffrn_orient_matrix_UB_23 -0.0320975000 _diffrn_orient_matrix_UB_31 -0.0128116000 _diffrn_orient_matrix_UB_32 -0.0543758000 _diffrn_orient_matrix_UB_33 -0.0267522000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1378 _diffrn_reflns_av_unetI/netI 0.1145 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9371 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.026 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 3.161 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 5.831 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.09078 _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 1.815 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.634 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2447 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.007 _refine_ls_R_factor_all 0.1174 _refine_ls_R_factor_gt 0.0750 _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^)+(0.0704P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1481 _refine_ls_wR_factor_ref 0.1788 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1526 _reflns_number_total 2447 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL shC_547_FlDu in P21/c #14 shc_547_fldu.res created by SHELXL-2018/3 at 09:44:38 on 13-Jun-2018 REM reset to P21/c #14 CELL 0.71073 8.69886 10.76937 15.06687 90 99.8665 90 ZERR 4 0.00108 0.00152 0.00172 0 0.0118 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 44 48 8 8 12 EQIV $1 -1+X,+Y,+Z EQIV $2 1-X,1-Y,-Z EQIV $3 1-X,-0.5+Y,0.5-Z L.S. 10 PLAN 5 SIZE 0.28 0.35 0.35 RTAB x1 Br1 Br2_$1 HTAB O1 O2_$2 HTAB C10 N2_$3 FREE Br2 Br1_$1 htab BOND fmap 2 acta SHEL 99 0.84 OMIT 7 1 2 OMIT 7 1 0 REM REM REM WGHT 0.070400 FVAR 4.70465 BR2 3 0.690350 0.351991 0.435572 11.00000 0.04569 0.05982 = 0.04390 0.00523 -0.00117 0.00799 BR1 3 0.089818 0.290618 0.514286 11.00000 0.06481 0.09737 = 0.05687 0.02898 0.01950 -0.00842 O1 5 0.660710 0.434061 0.079874 11.00000 0.06021 0.11820 = 0.03368 0.00081 0.01095 0.03543 AFIX 147 H1 2 0.628833 0.446329 0.026160 11.00000 -1.50000 AFIX 0 N2 4 0.553255 0.637424 0.294127 11.00000 0.05891 0.04776 = 0.04881 0.00768 0.00937 0.00735 N1 4 0.523249 0.516467 0.282423 11.00000 0.04516 0.03561 = 0.02664 -0.00052 0.00584 -0.00124 C7 1 0.185846 0.571028 0.237404 11.00000 0.03075 0.04784 = 0.04216 -0.00007 0.00153 0.00184 AFIX 13 H7 2 0.270879 0.605177 0.209824 11.00000 -1.20000 AFIX 0 O2 5 0.435052 0.522603 0.094600 11.00000 0.05306 0.10546 = 0.03570 0.00045 0.01180 0.01968 C1 1 0.222219 0.358532 0.439596 11.00000 0.05177 0.04785 = 0.03219 0.00483 0.00393 0.00157 C2 1 0.377923 0.332101 0.459389 11.00000 0.06670 0.03349 = 0.03617 0.00493 0.00567 0.00369 AFIX 43 H2 2 0.417121 0.279268 0.506704 11.00000 -1.20000 AFIX 0 O3 5 0.646203 0.675884 0.248238 11.00000 0.07161 0.07160 = 0.06984 0.01468 0.01558 -0.02719 C4 1 0.416558 0.463936 0.335170 11.00000 0.03365 0.03658 = 0.02583 -0.00221 0.00230 0.00194 C5 1 0.259398 0.488952 0.315300 11.00000 0.04133 0.03862 = 0.01975 0.00049 -0.00028 0.00687 C10 1 0.601247 0.442135 0.224258 11.00000 0.05850 0.05332 = 0.03823 0.00185 0.01700 0.00517 AFIX 23 H10A 2 0.576783 0.355441 0.232385 11.00000 -1.20000 H10B 2 0.713052 0.452204 0.242288 11.00000 -1.20000 AFIX 0 C11 1 0.557881 0.474057 0.126677 11.00000 0.02958 0.06441 = 0.03925 -0.01343 0.00579 0.00633 C8 1 0.081948 0.496196 0.165529 11.00000 0.08838 0.07176 = 0.04692 0.00606 -0.02398 -0.00671 AFIX 137 H8A 2 0.140108 0.427844 0.147233 11.00000 -1.50000 H8B 2 0.046051 0.548310 0.114488 11.00000 -1.50000 H8C 2 -0.006031 0.465102 0.189405 11.00000 -1.50000 AFIX 0 C3 1 0.476148 0.386482 0.406738 11.00000 0.02780 0.04446 = 0.03436 0.00369 -0.00028 0.01386 C6 1 0.161834 0.436168 0.370413 11.00000 0.04633 0.04988 = 0.03771 -0.00241 0.00661 0.00263 AFIX 43 H6 2 0.055677 0.454071 0.359831 11.00000 -1.20000 AFIX 0 C9 1 0.097009 0.681405 0.269003 11.00000 0.06332 0.05399 = 0.06623 0.01151 0.01627 0.01466 AFIX 137 H9A 2 -0.000251 0.652934 0.283567 11.00000 -1.50000 H9B 2 0.077157 0.742127 0.221779 11.00000 -1.50000 H9C 2 0.158641 0.718087 0.321396 11.00000 -1.50000 AFIX 0 HKLF 4 REM shC_547_FlDu in P21/c #14 REM wR2 = 0.1788, GooF = S = 1.007, Restrained GooF = 1.007 for all data REM R1 = 0.0750 for 1526 Fo > 4sig(Fo) and 0.1174 for all 2447 data REM 166 parameters refined using 0 restraints END WGHT 0.0704 0.0000 REM Instructions for potential hydrogen bonds HTAB O1 O2_$2 HTAB C10 N2_$3 REM Highest difference peak 0.634, deepest hole -0.995, 1-sigma level 0.156 Q1 1 0.3217 0.4558 0.5503 11.00000 0.05 0.63 Q2 1 0.4568 0.1947 0.4159 11.00000 0.05 0.54 Q3 1 0.6581 0.6497 0.1082 11.00000 0.05 0.53 Q4 1 -0.0741 0.4847 0.4724 11.00000 0.05 0.53 Q5 1 0.6817 0.3500 0.4997 11.00000 0.05 0.52 REM The information below was added by Olex2. REM REM R1 = 0.0750 for 1526 Fo > 4sig(Fo) and 0.1174 for all 11576 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.63, deepest hole -1.00 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1174 REM R1_gt = 0.0750 REM wR_ref = 0.1788 REM GOOF = 1.007 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11576 REM Reflections_gt = 1526 REM Parameters = n/a REM Hole = -1.00 REM Peak = 0.63 REM Flack = n/a ; _cod_data_source_file d0ra02368j2.cif _cod_data_source_block shc_547_fldu _cod_database_code 7240370 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C20H20N4O1Br1 _chemical_oxdiff_usercomment I_485 _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 0.292 _shelx_estimated_absorpt_t_min 0.235 _reflns_odcompleteness_completeness 99.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C7(H7) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6) 2.d Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1) ; _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 Br2 Br 0.69035(10) 0.35199(9) 0.43557(6) 0.0508(4) Uani 1 1 d . . . . . Br1 Br 0.08982(12) 0.29062(11) 0.51429(7) 0.0720(4) Uani 1 1 d . . . . . O1 O 0.6607(7) 0.4341(7) 0.0799(4) 0.070(2) Uani 1 1 d . . . . . H1 H 0.628833 0.446329 0.026160 0.106 Uiso 1 1 calc GR . . . . N2 N 0.5533(9) 0.6374(7) 0.2941(5) 0.0518(19) Uani 1 1 d . . . . . N1 N 0.5232(7) 0.5165(6) 0.2824(4) 0.0358(15) Uani 1 1 d . . . . . C7 C 0.1858(9) 0.5710(7) 0.2374(5) 0.041(2) Uani 1 1 d . . . . . H7 H 0.270879 0.605177 0.209824 0.049 Uiso 1 1 calc R . . . . O2 O 0.4351(7) 0.5226(7) 0.0946(4) 0.0642(18) Uani 1 1 d . . . . . C1 C 0.2222(10) 0.3585(8) 0.4396(5) 0.044(2) Uani 1 1 d . . . . . C2 C 0.3779(10) 0.3321(7) 0.4594(5) 0.046(2) Uani 1 1 d . . . . . H2 H 0.417121 0.279268 0.506704 0.055 Uiso 1 1 calc R . . . . O3 O 0.6462(8) 0.6759(6) 0.2482(4) 0.071(2) Uani 1 1 d . . . . . C4 C 0.4166(8) 0.4639(7) 0.3352(5) 0.0324(17) Uani 1 1 d . . . . . C5 C 0.2594(9) 0.4890(7) 0.3153(5) 0.0339(18) Uani 1 1 d . . . . . C10 C 0.6012(10) 0.4421(8) 0.2243(5) 0.049(2) Uani 1 1 d . . . . . H10A H 0.576783 0.355441 0.232385 0.059 Uiso 1 1 calc R . . . . H10B H 0.713052 0.452204 0.242288 0.059 Uiso 1 1 calc R . . . . C11 C 0.5579(9) 0.4741(8) 0.1267(6) 0.044(2) Uani 1 1 d . . . . . C8 C 0.0819(12) 0.4962(9) 0.1655(6) 0.073(3) Uani 1 1 d . . . . . H8A H 0.140108 0.427844 0.147233 0.110 Uiso 1 1 calc GR . . . . H8B H 0.046051 0.548310 0.114488 0.110 Uiso 1 1 calc GR . . . . H8C H -0.006031 0.465102 0.189405 0.110 Uiso 1 1 calc GR . . . . C3 C 0.4761(8) 0.3865(7) 0.4067(5) 0.0362(19) Uani 1 1 d . . . . . C6 C 0.1618(10) 0.4362(7) 0.3704(5) 0.045(2) Uani 1 1 d . . . . . H6 H 0.055677 0.454071 0.359831 0.054 Uiso 1 1 calc R . . . . C9 C 0.0970(11) 0.6814(8) 0.2690(6) 0.061(3) Uani 1 1 d . . . . . H9A H -0.000251 0.652934 0.283567 0.091 Uiso 1 1 calc GR . . . . H9B H 0.077157 0.742127 0.221779 0.091 Uiso 1 1 calc GR . . . . H9C H 0.158641 0.718087 0.321396 0.091 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 Br2 0.0457(6) 0.0598(7) 0.0439(6) 0.0052(4) -0.0012(4) 0.0080(4) Br1 0.0648(8) 0.0974(9) 0.0569(7) 0.0290(6) 0.0195(5) -0.0084(6) O1 0.060(4) 0.118(6) 0.034(4) 0.001(4) 0.011(3) 0.035(4) N2 0.059(5) 0.048(5) 0.049(5) 0.008(4) 0.009(4) 0.007(4) N1 0.045(4) 0.036(4) 0.027(3) -0.001(3) 0.006(3) -0.001(3) C7 0.031(5) 0.048(5) 0.042(5) 0.000(4) 0.002(4) 0.002(4) O2 0.053(4) 0.105(5) 0.036(3) 0.000(3) 0.012(3) 0.020(4) C1 0.052(6) 0.048(6) 0.032(5) 0.005(4) 0.004(4) 0.002(4) C2 0.067(7) 0.033(5) 0.036(5) 0.005(4) 0.006(4) 0.004(4) O3 0.072(5) 0.072(5) 0.070(5) 0.015(4) 0.016(4) -0.027(4) C4 0.034(5) 0.037(5) 0.026(4) -0.002(3) 0.002(3) 0.002(3) C5 0.041(5) 0.039(5) 0.020(4) 0.000(3) 0.000(3) 0.007(3) C10 0.059(6) 0.053(6) 0.038(5) 0.002(4) 0.017(4) 0.005(4) C11 0.030(5) 0.064(6) 0.039(5) -0.013(4) 0.006(4) 0.006(4) C8 0.088(8) 0.072(7) 0.047(6) 0.006(5) -0.024(5) -0.007(6) C3 0.028(4) 0.044(5) 0.034(4) 0.004(4) 0.000(3) 0.014(3) C6 0.046(5) 0.050(6) 0.038(5) -0.002(4) 0.007(4) 0.003(4) C9 0.063(7) 0.054(6) 0.066(7) 0.012(5) 0.016(5) 0.015(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 O3 N2 N1 112.9(7) . . ? N2 N1 C4 116.2(6) . . ? N2 N1 C10 121.4(6) . . ? C4 N1 C10 122.3(6) . . ? C5 C7 C9 112.2(6) . . ? C8 C7 C5 111.3(7) . . ? C8 C7 C9 111.2(7) . . ? C2 C1 Br1 118.2(6) . . ? C2 C1 C6 122.0(8) . . ? C6 C1 Br1 119.8(7) . . ? C1 C2 C3 118.1(8) . . ? C5 C4 N1 121.0(7) . . ? C5 C4 C3 120.7(7) . . ? C3 C4 N1 118.3(7) . . ? C4 C5 C7 123.6(7) . . ? C4 C5 C6 118.1(7) . . ? C6 C5 C7 118.3(7) . . ? N1 C10 C11 113.9(7) . . ? O1 C11 C10 112.0(7) . . ? O2 C11 O1 124.5(8) . . ? O2 C11 C10 123.2(7) . . ? C2 C3 Br2 117.9(6) . . ? C2 C3 C4 120.7(7) . . ? C4 C3 Br2 121.4(6) . . ? C1 C6 C5 120.3(8) . . ? 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 Br2 C3 1.876(7) . ? Br1 C1 1.890(8) . ? O1 C11 1.303(9) . ? N2 N1 1.334(9) . ? N2 O3 1.223(8) . ? N1 C4 1.437(8) . ? N1 C10 1.440(9) . ? C7 C5 1.520(10) . ? C7 C8 1.518(11) . ? C7 C9 1.537(10) . ? O2 C11 1.213(9) . ? C1 C2 1.366(11) . ? C1 C6 1.369(11) . ? C2 C3 1.391(10) . ? C4 C5 1.375(10) . ? C4 C3 1.391(10) . ? C5 C6 1.405(10) . ? C10 C11 1.494(11) . ? 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 O1 H1 O2 0.82 1.84 2.659(8) 177.6 3_665 yes C10 H10A N2 0.97 2.61 3.539(11) 161.1 2_645 yes