#------------------------------------------------------------------------------ #$Date: 2026-06-04 23:39:08 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306219 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577375.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_1577375 loop_ _publ_author_name 'Makarov, Anton S.' 'Yi, Liang' 'Maity, Bholanath' 'Cavallo, Luigi' 'Rueping, Magnus' _publ_section_title ; Pulsed electrolysis enables unexpected lactonization of bicyclobutane carboxylic acids ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC01541G _journal_year 2026 _chemical_formula_moiety 'C11 H9 Br O2' _chemical_formula_sum 'C11 H9 Br O2' _chemical_formula_weight 253.09 _chemical_melting_point 353 _chemical_name_systematic 4-bromo-1-phenyl-2-oxabicyclo[2.1.1]hexan-3-one _chemical_properties_physical acid-sensitive _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-10-03 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2025-10-06 deposited with the CCDC. 2026-05-21 downloaded from the CCDC. ; _cell_angle_alpha 69.2060(10) _cell_angle_beta 80.6720(10) _cell_angle_gamma 88.2460(10) _cell_formula_units_Z 2 _cell_length_a 6.3703(2) _cell_length_b 9.0082(3) _cell_length_c 9.2840(3) _cell_measurement_reflns_used 9760 _cell_measurement_temperature 120.00 _cell_measurement_theta_max 68.02 _cell_measurement_theta_min 5.16 _cell_volume 491.26(3) _computing_cell_refinement 'SAINT V8.41 (?, 2016)' _computing_data_reduction 'SAINT V8.41 (?, 2016)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 120.00 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_unetI/netI 0.0114 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 25934 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.060 _diffrn_reflns_theta_min 5.164 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.456 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_correction_T_min 0.4673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1184 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.6206. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.711 _exptl_crystal_description prisms _exptl_crystal_F_000 252 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethyl acetate, n-hexane' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.496 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1781 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0193 _refine_ls_R_factor_gt 0.0193 _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^)+(0.0107P)^2^+0.5876P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0457 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1779 _reflns_number_total 1781 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc01541g2.cif _cod_data_source_block cu_asm5622_0m _cod_database_code 1577375 _shelx_shelxl_version_number 2018/3 _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 0.772 _shelx_estimated_absorpt_t_min 0.611 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C5(H5A,H5B) 2.b Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C9(H9), C10(H10), C11(H11) ; _shelx_res_file ; TITL cu_asm5622_0m_a.res in P-1 cu_asm5622_0m.res created by SHELXL-2018/3 at 02:55:23 on 03-Oct-2025 REM Old TITL cu_asm5622_0m_a.res in P-1 REM SHELXT solution in P-1: R1 0.072, Rweak 0.013, Alpha 0.041 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C11 O2 Br CELL 1.54178 6.3703 9.0082 9.284 69.206 80.672 88.246 ZERR 2 0.0002 0.0003 0.0003 0.001 0.001 0.001 LATT 1 SFAC C H Br O UNIT 22 18 2 4 L.S. 50 PLAN 10 SIZE 0.05 0.1 0.1 TEMP -153.15 CONF list 4 MORE -1 BOND $H fmap 2 53 acta OMIT -1 4 1 REM REM REM WGHT 0.010700 0.587600 FVAR 1.27337 O1 4 0.939771 0.638305 0.636793 11.00000 0.01235 0.01902 = 0.02088 -0.00428 -0.00679 0.00168 C1 1 1.014641 0.764738 0.506392 11.00000 0.01597 0.01733 = 0.01999 -0.00918 -0.00343 0.00113 BR1 3 0.853253 1.003752 0.247706 11.00000 0.02488 0.01932 = 0.01655 0.00041 -0.00145 -0.00308 O2 4 1.196738 0.808390 0.464817 11.00000 0.01290 0.02889 = 0.03019 -0.01062 -0.00226 -0.00264 C2 1 0.814799 0.824374 0.437752 11.00000 0.01583 0.01380 = 0.01375 -0.00257 -0.00239 -0.00002 C3 1 0.711680 0.664403 0.454348 11.00000 0.01508 0.01618 = 0.01643 -0.00483 -0.00285 -0.00147 AFIX 23 H3A 2 0.807078 0.593942 0.414412 11.00000 -1.20000 H3B 2 0.570682 0.672124 0.420799 11.00000 -1.20000 AFIX 0 C4 1 0.706536 0.639223 0.628965 11.00000 0.01143 0.01574 = 0.01677 -0.00592 -0.00411 0.00159 C5 1 0.660168 0.817618 0.588587 11.00000 0.01557 0.01329 = 0.01629 -0.00357 -0.00032 0.00014 AFIX 23 H5A 2 0.715471 0.868512 0.654004 11.00000 -1.20000 H5B 2 0.511901 0.846665 0.573995 11.00000 -1.20000 AFIX 0 C6 1 0.591297 0.503675 0.759296 11.00000 0.01795 0.01538 = 0.01423 -0.00592 -0.00525 -0.00043 C7 1 0.688453 0.357111 0.811555 11.00000 0.02152 0.01925 = 0.01824 -0.00701 -0.00494 0.00233 AFIX 43 H7 2 0.832603 0.346777 0.770740 11.00000 -1.20000 AFIX 0 C8 1 0.574686 0.227226 0.922647 11.00000 0.03626 0.01538 = 0.01999 -0.00424 -0.00736 0.00162 AFIX 43 H8 2 0.640609 0.127500 0.957379 11.00000 -1.20000 AFIX 0 C9 1 0.365203 0.241818 0.983490 11.00000 0.03615 0.02061 = 0.01526 -0.00357 0.00149 -0.00997 AFIX 43 H9 2 0.287483 0.152120 1.059520 11.00000 -1.20000 AFIX 0 C10 1 0.268723 0.387290 0.933527 11.00000 0.02347 0.02726 = 0.02237 -0.01088 0.00357 -0.00482 AFIX 43 H10 2 0.125307 0.397361 0.976110 11.00000 -1.20000 AFIX 0 C11 1 0.381359 0.518481 0.821245 11.00000 0.02020 0.01813 = 0.01955 -0.00708 -0.00306 0.00052 AFIX 43 H11 2 0.314947 0.618047 0.786938 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_asm5622_0m_a.res in P-1 REM wR2 = 0.0457, GooF = S = 1.114, Restrained GooF = 1.114 for all data REM R1 = 0.0193 for 1779 Fo > 4sig(Fo) and 0.0193 for all 1781 data REM 127 parameters refined using 0 restraints END WGHT 0.0110 0.5868 REM Highest difference peak 0.496, deepest hole -0.330, 1-sigma level 0.053 Q1 1 0.7232 1.0179 0.2209 11.00000 0.05 0.50 Q2 1 0.9230 0.8031 0.4602 11.00000 0.05 0.40 Q3 1 0.7459 0.8429 0.5067 11.00000 0.05 0.33 Q4 1 0.6402 0.5610 0.6964 11.00000 0.05 0.31 Q5 1 0.8184 0.9015 0.3640 11.00000 0.05 0.31 Q6 1 0.6690 0.7178 0.6344 11.00000 0.05 0.29 Q7 1 0.9909 0.9779 0.2760 11.00000 0.05 0.28 Q8 1 0.5099 0.5155 0.8111 11.00000 0.05 0.27 Q9 1 0.7671 0.7591 0.4213 11.00000 0.05 0.27 Q10 1 0.6437 0.4421 0.7929 11.00000 0.05 0.27 ; _shelx_res_checksum 11233 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 O1 O 0.93977(19) 0.63830(15) 0.63679(15) 0.0177(3) Uani 1 1 d . . . . . C1 C 1.0146(3) 0.7647(2) 0.5064(2) 0.0170(4) Uani 1 1 d . . . . . Br1 Br 0.85325(3) 1.00375(2) 0.24771(2) 0.02226(8) Uani 1 1 d . . . . . O2 O 1.1967(2) 0.80839(16) 0.46482(16) 0.0240(3) Uani 1 1 d . . . . . C2 C 0.8148(3) 0.8244(2) 0.4378(2) 0.0151(3) Uani 1 1 d . . . . . C3 C 0.7117(3) 0.6644(2) 0.4543(2) 0.0161(4) Uani 1 1 d . . . . . H3A H 0.807078 0.593942 0.414412 0.019 Uiso 1 1 calc R U . . . H3B H 0.570682 0.672124 0.420799 0.019 Uiso 1 1 calc R U . . . C4 C 0.7065(3) 0.6392(2) 0.6290(2) 0.0144(3) Uani 1 1 d . . . . . C5 C 0.6602(3) 0.8176(2) 0.5886(2) 0.0158(4) Uani 1 1 d . . . . . H5A H 0.715471 0.868512 0.654004 0.019 Uiso 1 1 calc R U . . . H5B H 0.511901 0.846665 0.573995 0.019 Uiso 1 1 calc R U . . . C6 C 0.5913(3) 0.5037(2) 0.7593(2) 0.0153(3) Uani 1 1 d . . . . . C7 C 0.6885(3) 0.3571(2) 0.8116(2) 0.0194(4) Uani 1 1 d . . . . . H7 H 0.832603 0.346777 0.770740 0.023 Uiso 1 1 calc R U . . . C8 C 0.5747(3) 0.2272(2) 0.9226(2) 0.0241(4) Uani 1 1 d . . . . . H8 H 0.640609 0.127500 0.957379 0.029 Uiso 1 1 calc R U . . . C9 C 0.3652(3) 0.2418(2) 0.9835(2) 0.0252(4) Uani 1 1 d . . . . . H9 H 0.287483 0.152120 1.059520 0.030 Uiso 1 1 calc R U . . . C10 C 0.2687(3) 0.3873(2) 0.9335(2) 0.0245(4) Uani 1 1 d . . . . . H10 H 0.125307 0.397361 0.976110 0.029 Uiso 1 1 calc R U . . . C11 C 0.3814(3) 0.5185(2) 0.8212(2) 0.0192(4) Uani 1 1 d . . . . . H11 H 0.314947 0.618047 0.786938 0.023 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 O1 0.0123(6) 0.0190(6) 0.0209(6) -0.0043(5) -0.0068(5) 0.0017(5) C1 0.0160(9) 0.0173(9) 0.0200(9) -0.0092(7) -0.0034(7) 0.0011(7) Br1 0.02488(12) 0.01932(11) 0.01655(11) 0.00041(8) -0.00145(7) -0.00308(7) O2 0.0129(6) 0.0289(7) 0.0302(7) -0.0106(6) -0.0023(5) -0.0026(5) C2 0.0158(8) 0.0138(8) 0.0137(8) -0.0026(7) -0.0024(7) 0.0000(7) C3 0.0151(8) 0.0162(9) 0.0164(9) -0.0048(7) -0.0029(7) -0.0015(7) C4 0.0114(8) 0.0157(8) 0.0168(9) -0.0059(7) -0.0041(6) 0.0016(6) C5 0.0156(8) 0.0133(8) 0.0163(9) -0.0036(7) -0.0003(7) 0.0001(7) C6 0.0180(9) 0.0154(8) 0.0142(8) -0.0059(7) -0.0053(7) -0.0004(7) C7 0.0215(9) 0.0193(9) 0.0182(9) -0.0070(7) -0.0049(7) 0.0023(7) C8 0.0363(11) 0.0154(9) 0.0200(9) -0.0042(8) -0.0074(8) 0.0016(8) C9 0.0362(11) 0.0206(10) 0.0153(9) -0.0036(8) 0.0015(8) -0.0100(8) C10 0.0235(10) 0.0273(10) 0.0224(10) -0.0109(8) 0.0036(8) -0.0048(8) C11 0.0202(9) 0.0181(9) 0.0195(9) -0.0071(7) -0.0031(7) 0.0005(7) 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' O O 0.0492 0.0322 '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 C1 O1 C4 101.58(13) . . ? O1 C1 C2 102.64(14) . . ? O2 C1 O1 124.96(17) . . ? O2 C1 C2 132.39(17) . . ? C1 C2 Br1 115.80(12) . . ? C1 C2 C3 99.84(14) . . ? C1 C2 C4 77.09(11) . . ? C1 C2 C5 99.97(14) . . ? Br1 C2 C4 167.09(11) . . ? C3 C2 Br1 123.21(12) . . ? C3 C2 C4 49.95(9) . . ? C3 C2 C5 87.58(13) . . ? C5 C2 Br1 124.38(12) . . ? C5 C2 C4 49.72(9) . . ? C2 C3 H3A 115.2 . . ? C2 C3 H3B 115.2 . . ? C2 C3 C4 80.14(12) . . ? H3A C3 H3B 112.3 . . ? C4 C3 H3A 115.2 . . ? C4 C3 H3B 115.2 . . ? O1 C4 C2 78.69(10) . . ? O1 C4 C3 100.92(13) . . ? O1 C4 C5 101.39(13) . . ? C3 C4 C2 49.90(9) . . ? C5 C4 C2 50.31(9) . . ? C5 C4 C3 88.02(13) . . ? C6 C4 O1 111.04(14) . . ? C6 C4 C2 169.96(14) . . ? C6 C4 C3 123.41(15) . . ? C6 C4 C5 127.03(15) . . ? C2 C5 H5A 115.3 . . ? C2 C5 H5B 115.3 . . ? C4 C5 C2 79.96(12) . . ? C4 C5 H5A 115.3 . . ? C4 C5 H5B 115.3 . . ? H5A C5 H5B 112.3 . . ? C7 C6 C4 119.94(16) . . ? C11 C6 C4 120.18(16) . . ? C11 C6 C7 119.69(17) . . ? C6 C7 H7 120.0 . . ? C8 C7 C6 119.97(18) . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.29(18) . . ? C9 C8 H8 119.9 . . ? C8 C9 H9 120.0 . . ? C8 C9 C10 120.02(18) . . ? C10 C9 H9 120.0 . . ? C9 C10 H10 119.9 . . ? C9 C10 C11 120.15(18) . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 119.87(17) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? 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 O1 C1 1.363(2) . ? O1 C4 1.499(2) . ? C1 O2 1.193(2) . ? C1 C2 1.514(2) . ? Br1 C2 1.9089(17) . ? C2 C3 1.549(2) . ? C2 C5 1.559(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.550(2) . ? C4 C5 1.546(2) . ? C4 C6 1.487(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.398(3) . ? C6 C11 1.390(3) . ? C7 H7 0.9500 . ? C7 C8 1.382(3) . ? C8 H8 0.9500 . ? C8 C9 1.384(3) . ? C9 H9 0.9500 . ? C9 C10 1.386(3) . ? C10 H10 0.9500 . ? C10 C11 1.390(3) . ? C11 H11 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 O1 C1 C2 Br1 -179.28(11) . . . . ? O1 C1 C2 C3 -44.75(16) . . . . ? O1 C1 C2 C4 0.05(12) . . . . ? O1 C1 C2 C5 44.51(16) . . . . ? O1 C4 C5 C2 64.72(13) . . . . ? O1 C4 C6 C7 -36.1(2) . . . . ? O1 C4 C6 C11 148.93(15) . . . . ? C1 O1 C4 C2 0.05(12) . . . . ? C1 O1 C4 C3 45.01(15) . . . . ? C1 O1 C4 C5 -45.16(15) . . . . ? C1 O1 C4 C6 177.47(14) . . . . ? C1 C2 C3 C4 63.78(13) . . . . ? C1 C2 C5 C4 -63.50(13) . . . . ? Br1 C2 C3 C4 -166.32(13) . . . . ? Br1 C2 C5 C4 165.52(14) . . . . ? O2 C1 C2 Br1 0.1(3) . . . . ? O2 C1 C2 C3 134.6(2) . . . . ? O2 C1 C2 C4 179.4(2) . . . . ? O2 C1 C2 C5 -136.1(2) . . . . ? C2 C3 C4 O1 -64.94(13) . . . . ? C2 C3 C4 C5 36.27(12) . . . . ? C2 C3 C4 C6 170.63(17) . . . . ? C2 C4 C6 C7 129.3(8) . . . . ? C2 C4 C6 C11 -45.7(9) . . . . ? C3 C2 C5 C4 36.06(12) . . . . ? C3 C4 C5 C2 -36.02(12) . . . . ? C3 C4 C6 C7 83.7(2) . . . . ? C3 C4 C6 C11 -91.3(2) . . . . ? C4 O1 C1 O2 -179.51(17) . . . . ? C4 O1 C1 C2 -0.06(16) . . . . ? C4 C6 C7 C8 -174.06(17) . . . . ? C4 C6 C11 C10 174.38(17) . . . . ? C5 C2 C3 C4 -35.92(12) . . . . ? C5 C4 C6 C7 -159.80(17) . . . . ? C5 C4 C6 C11 25.2(3) . . . . ? C6 C4 C5 C2 -167.64(17) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C6 C11 C10 -0.6(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 0.6(3) . . . . ? C9 C10 C11 C6 -0.1(3) . . . . ? C11 C6 C7 C8 1.0(3) . . . . ?