#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:15:43 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257983 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240371.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_7240371 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_page_last 15664 _journal_paper_doi 10.1039/D0RA02368J _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C11 H10 Br2 N2 O2' _chemical_formula_sum 'C11 H10 Br2 N2 O2' _chemical_formula_weight 362.03 _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 100.771(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0273(13) _cell_length_b 9.0598(6) _cell_length_c 16.3781(16) _cell_measurement_reflns_used 2155 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0590 _cell_measurement_theta_min 3.6150 _cell_volume 1315.9(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 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 65.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -19.0000 -30.0000 119 #__ type_ start__ end____ width___ exp.time_ 2 omega -15.00 46.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -99.0000 -90.0000 61 #__ type_ start__ end____ width___ exp.time_ 3 omega 55.00 81.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -178.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega 36.00 62.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -99.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega -1.00 86.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 57.0000 150.0000 87 #__ type_ start__ end____ width___ exp.time_ 6 omega -49.00 -13.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.8352 -57.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 7 omega -86.00 -13.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -19.2884 -57.0000 -90.0000 73 ; _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 -0.0740785000 _diffrn_orient_matrix_UB_12 -0.0031426000 _diffrn_orient_matrix_UB_13 -0.0239756000 _diffrn_orient_matrix_UB_21 0.0253548000 _diffrn_orient_matrix_UB_22 0.0362058000 _diffrn_orient_matrix_UB_23 -0.0332381000 _diffrn_orient_matrix_UB_31 0.0165519000 _diffrn_orient_matrix_UB_32 -0.0692853000 _diffrn_orient_matrix_UB_33 -0.0162839000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8750 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.021 _diffrn_reflns_theta_max 25.021 _diffrn_reflns_theta_min 3.214 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 6.152 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.24758 _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 1.827 _exptl_crystal_description prism _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.411 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2311 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0262P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.0786 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1600 _reflns_number_total 2311 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL shc_544_FlDu in P21/c #14 shc_544_fldu.res created by SHELXL-2018/3 at 09:45:22 on 14-Jun-2018 REM reset to P21/c #14 CELL 0.71073 9.02727 9.05979 16.37811 90 100.7713 90 ZERR 4 0.00132 0.00064 0.00164 0 0.0126 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 44 40 8 8 8 EQIV $1 +X,1+Y,+Z EQIV $2 +X,2.5-Y,0.5+Z ISOR 0.001 0.02 Br1 L.S. 10 PLAN 5 SIZE 0.22 0.22 0.35 HTAB C2 O2_$1 RTAB x1 Br1 Br2_$2 BOND fmap 2 acta SHEL 99 0.84 OMIT 0 2 0 OMIT 0 0 4 OMIT -2 1 1 OMIT -1 1 5 OMIT -1 6 6 REM REM REM WGHT 0.026200 FVAR 5.15812 BR1 3 0.226816 1.407444 0.405670 11.00000 0.14521 0.03062 = 0.06161 -0.00798 0.02834 0.00440 BR2 3 0.250772 1.056995 0.126801 11.00000 0.12021 0.05034 = 0.04344 0.00031 0.02640 0.00114 O1 5 0.169421 0.602477 0.194429 11.00000 0.06882 0.03618 = 0.06719 -0.01728 0.00871 -0.00561 O2 5 0.386045 0.486728 0.181712 11.00000 0.10969 0.03174 = 0.08759 -0.00631 0.04566 0.01059 N1 4 0.247854 0.802099 0.252127 11.00000 0.04258 0.03045 = 0.04200 -0.00346 0.01169 0.00035 N2 4 0.122143 0.732797 0.223953 11.00000 0.04600 0.04783 = 0.07338 -0.01605 0.00232 -0.00069 C1 1 0.233025 1.217629 0.358209 11.00000 0.05206 0.02717 = 0.04516 -0.00023 0.01109 0.00410 C2 1 0.236159 1.208524 0.274828 11.00000 0.05082 0.02950 = 0.04654 0.00193 0.01292 -0.00034 AFIX 43 H2 2 0.234502 1.293135 0.242518 11.00000 -1.20000 AFIX 0 C3 1 0.241817 1.070613 0.240588 11.00000 0.03932 0.04023 = 0.03760 0.00200 0.01345 0.00043 C4 1 0.239254 0.945937 0.289246 11.00000 0.03365 0.03006 = 0.04250 -0.00211 0.01045 0.00307 C5 1 0.234541 0.953386 0.373025 11.00000 0.04082 0.03310 = 0.04126 0.00044 0.01019 0.00068 C6 1 0.232024 1.094485 0.407961 11.00000 0.06415 0.03720 = 0.04010 -0.00473 0.01112 -0.00168 AFIX 43 H6 2 0.229699 1.105139 0.464184 11.00000 -1.20000 AFIX 0 C7 1 0.235680 0.817207 0.428008 11.00000 0.07660 0.02744 = 0.04912 0.00288 0.01455 -0.00155 AFIX 13 H7 2 0.224255 0.730707 0.391439 11.00000 -1.20000 AFIX 0 C8 1 0.385141 0.802902 0.486159 11.00000 0.11042 0.05466 = 0.07166 0.02373 0.01124 0.01463 AFIX 137 H8A 2 0.464570 0.799451 0.454562 11.00000 -1.20000 H8B 2 0.386205 0.713869 0.518045 11.00000 -1.20000 H8C 2 0.400007 0.886260 0.522970 11.00000 -1.20000 AFIX 0 C9 1 0.104520 0.816795 0.473726 11.00000 0.10379 0.06451 = 0.09061 0.02856 0.04343 -0.00936 AFIX 137 H9A 2 0.112648 0.900095 0.510524 11.00000 -1.50000 H9B 2 0.106233 0.727366 0.505330 11.00000 -1.50000 H9C 2 0.011546 0.822663 0.434303 11.00000 -1.50000 AFIX 0 C10 1 0.372118 0.730127 0.243349 11.00000 0.05028 0.03219 = 0.07633 -0.00503 0.02520 -0.00037 AFIX 43 H10 2 0.470672 0.763279 0.259850 11.00000 -1.20000 AFIX 0 C11 1 0.327879 0.596057 0.204952 11.00000 0.06538 0.03575 = 0.04661 0.00341 0.02075 0.00061 HKLF 4 REM shc_544_FlDu in P21/c #14 REM wR2 = 0.0786, GooF = S = 1.043, Restrained GooF = 1.046 for all data REM R1 = 0.0385 for 1600 Fo > 4sig(Fo) and 0.0685 for all 2311 data REM 156 parameters refined using 6 restraints END WGHT 0.0262 0.0000 REM Highest difference peak 0.411, deepest hole -0.470, 1-sigma level 0.069 Q1 1 0.1440 1.0270 0.1398 11.00000 0.05 0.41 Q2 1 0.3742 1.0456 0.1827 11.00000 0.05 0.31 Q3 1 0.0782 0.8188 0.1836 11.00000 0.05 0.27 Q4 1 0.3340 1.4263 0.4547 11.00000 0.05 0.27 Q5 1 0.3460 1.4290 0.4022 11.00000 0.05 0.26 REM The information below was added by Olex2. REM REM R1 = 0.0385 for 1600 Fo > 4sig(Fo) and 0.0685 for all 10742 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.41, deepest hole -0.47 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0685 REM R1_gt = 0.0385 REM wR_ref = 0.0786 REM GOOF = 1.043 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 10742 REM Reflections_gt = 1600 REM Parameters = n/a REM Hole = -0.47 REM Peak = 0.41 REM Flack = n/a ; _cod_data_source_file d0ra02368j2.cif _cod_data_source_block shc_544_fldu _cod_depositor_comments 'Adding full bibliography for 7240370--7240372.cif.' _cod_database_code 7240371 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C20H20N4O2Cl1 _chemical_oxdiff_usercomment I_191 _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 0.345 _shelx_estimated_absorpt_t_min 0.222 _reflns_odcompleteness_completeness 99.69 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, {H8A,H8B,H8C} of C8 At 1.5 times of: {H9A,H9B,H9C} of C9 2. Uiso/Uaniso restraints and constraints Uanis(Br1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02 3.a Ternary CH refined with riding coordinates: C7(H7) 3.b Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6), C10(H10) 3.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) ; _olex2_date_sample_data_collection 1518679427.4 _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 0.22682(7) 1.40744(4) 0.40567(3) 0.0780(2) Uani 1 1 d . U . . . Br2 Br 0.25077(7) 1.05700(5) 0.12680(3) 0.0699(2) Uani 1 1 d . . . . . O1 O 0.1694(3) 0.6025(3) 0.1944(2) 0.0579(9) Uani 1 1 d . . . . . O2 O 0.3860(4) 0.4867(3) 0.1817(2) 0.0728(10) Uani 1 1 d . . . . . N1 N 0.2479(4) 0.8021(3) 0.2521(2) 0.0379(8) Uani 1 1 d . . . . . N2 N 0.1221(4) 0.7328(3) 0.2240(2) 0.0569(10) Uani 1 1 d . . . . . C1 C 0.2330(4) 1.2176(4) 0.3582(3) 0.0412(10) Uani 1 1 d . . . . . C2 C 0.2362(4) 1.2085(4) 0.2748(3) 0.0418(10) Uani 1 1 d . . . . . H2 H 0.234502 1.293135 0.242518 0.050 Uiso 1 1 calc R . . . . C3 C 0.2418(4) 1.0706(4) 0.2406(3) 0.0382(10) Uani 1 1 d . . . . . C4 C 0.2393(4) 0.9459(4) 0.2892(3) 0.0350(10) Uani 1 1 d . . . . . C5 C 0.2345(4) 0.9534(4) 0.3730(3) 0.0381(10) Uani 1 1 d . . . . . C6 C 0.2320(4) 1.0945(4) 0.4080(3) 0.0470(11) Uani 1 1 d . . . . . H6 H 0.229699 1.105139 0.464184 0.056 Uiso 1 1 calc R . . . . C7 C 0.2357(5) 0.8172(4) 0.4280(3) 0.0507(12) Uani 1 1 d . . . . . H7 H 0.224255 0.730707 0.391439 0.061 Uiso 1 1 calc R . . . . C8 C 0.3851(6) 0.8029(5) 0.4862(3) 0.0797(16) Uani 1 1 d . . . . . H8A H 0.464570 0.799451 0.454562 0.096 Uiso 1 1 calc GR . . . . H8B H 0.386205 0.713869 0.518045 0.096 Uiso 1 1 calc GR . . . . H8C H 0.400007 0.886260 0.522970 0.096 Uiso 1 1 calc GR . . . . C9 C 0.1045(6) 0.8168(5) 0.4737(3) 0.0830(18) Uani 1 1 d . . . . . H9A H 0.112648 0.900095 0.510524 0.125 Uiso 1 1 calc GR . . . . H9B H 0.106233 0.727366 0.505330 0.125 Uiso 1 1 calc GR . . . . H9C H 0.011546 0.822663 0.434303 0.125 Uiso 1 1 calc GR . . . . C10 C 0.3721(5) 0.7301(4) 0.2433(3) 0.0512(12) Uani 1 1 d . . . . . H10 H 0.470672 0.763279 0.259850 0.061 Uiso 1 1 calc R . . . . C11 C 0.3279(5) 0.5961(4) 0.2050(3) 0.0479(11) Uani 1 1 d . . . . . 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 0.1452(6) 0.0306(3) 0.0616(4) -0.0080(2) 0.0283(4) 0.0044(2) Br2 0.1202(5) 0.0503(3) 0.0434(3) 0.0003(2) 0.0264(3) 0.0011(2) O1 0.069(2) 0.0362(16) 0.067(2) -0.0173(14) 0.0087(19) -0.0056(13) O2 0.110(3) 0.0317(16) 0.088(3) -0.0063(16) 0.046(2) 0.0106(16) N1 0.043(2) 0.0304(17) 0.042(2) -0.0035(15) 0.0117(19) 0.0003(16) N2 0.046(2) 0.048(2) 0.073(3) -0.016(2) 0.002(2) -0.0007(17) C1 0.052(3) 0.027(2) 0.045(3) -0.0002(18) 0.011(2) 0.0041(17) C2 0.051(3) 0.029(2) 0.047(3) 0.0019(19) 0.013(2) -0.0003(17) C3 0.039(3) 0.040(2) 0.038(3) 0.0020(18) 0.013(2) 0.0004(17) C4 0.034(2) 0.030(2) 0.042(3) -0.0021(18) 0.010(2) 0.0031(16) C5 0.041(3) 0.033(2) 0.041(3) 0.0004(18) 0.010(2) 0.0007(17) C6 0.064(3) 0.037(2) 0.040(3) -0.0047(19) 0.011(2) -0.0017(19) C7 0.077(3) 0.027(2) 0.049(3) 0.0029(19) 0.015(3) -0.002(2) C8 0.110(5) 0.055(3) 0.072(4) 0.024(3) 0.011(4) 0.015(3) C9 0.104(4) 0.065(3) 0.091(5) 0.029(3) 0.043(4) -0.009(3) C10 0.050(3) 0.032(2) 0.076(4) -0.005(2) 0.025(3) -0.0004(19) C11 0.065(3) 0.036(2) 0.047(3) 0.003(2) 0.021(3) 0.001(2) 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 N2 O1 C11 111.6(3) . . ? N2 N1 C4 118.1(3) . . ? N2 N1 C10 115.0(3) . . ? C10 N1 C4 126.9(3) . . ? N1 N2 O1 103.4(3) . . ? C2 C1 Br1 118.1(3) . . ? C2 C1 C6 122.8(3) . . ? C6 C1 Br1 119.2(3) . . ? C1 C2 C3 118.0(3) . . ? C2 C3 Br2 118.3(3) . . ? C2 C3 C4 120.0(4) . . ? C4 C3 Br2 121.6(3) . . ? C3 C4 N1 119.0(4) . . ? C5 C4 N1 118.4(3) . . ? C5 C4 C3 122.6(3) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 C7 123.2(3) . . ? C6 C5 C7 119.7(4) . . ? C1 C6 C5 119.5(4) . . ? C8 C7 C5 110.5(3) . . ? C8 C7 C9 112.2(4) . . ? C9 C7 C5 112.0(3) . . ? N1 C10 C11 107.5(4) . . ? O2 C11 O1 118.9(4) . . ? O2 C11 C10 138.5(5) . . ? C10 C11 O1 102.6(3) . . ? 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 1.892(3) . ? Br2 C3 1.884(4) . ? O1 N2 1.374(4) . ? O1 C11 1.410(5) . ? O2 C11 1.215(4) . ? N1 N2 1.304(4) . ? N1 C4 1.446(4) . ? N1 C10 1.328(4) . ? C1 C2 1.374(5) . ? C1 C6 1.383(5) . ? C2 C3 1.374(4) . ? C3 C4 1.385(5) . ? C4 C5 1.382(5) . ? C5 C6 1.402(5) . ? C5 C7 1.526(5) . ? C7 C8 1.505(6) . ? C7 C9 1.515(5) . ? C10 C11 1.392(5) . ? 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 O2 0.93 2.54 3.359(5) 147.1 1_565 yes