#------------------------------------------------------------------------------
#$Date: 2026-06-04 23:39:08 +0100 (Thu, 04 Jun 2026) $
#$Revision: 306219 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577374.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_1577374
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 H10 O2'
_chemical_formula_sum            'C11 H10 O2'
_chemical_formula_weight         174.19
_chemical_melting_point          333
_chemical_name_systematic        1-phenyl-2-oxabicyclo[2.1.1]hexan-3-one
_chemical_properties_physical    acid-sensitive
_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             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                90
_cell_angle_beta                 93.6180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5720(2)
_cell_length_b                   5.5244(2)
_cell_length_c                   20.5726(7)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      5.86
_cell_volume                     858.85(5)
_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      120.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         5.855
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF, n-hexane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0396P)^2^+0.3390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1465
_reflns_number_total             1563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc01541g2.cif
_cod_data_source_block           cu_asm599_1_a
_cod_database_code               1577374
_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   0.929
_shelx_estimated_absorpt_t_min   0.807
_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:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_shelx_res_file
;
TITL cu_ASM599_1_a.res in P2(1)/c
    cu_asm599_1_a.res
    created by SHELXL-2018/3 at 03:10:49 on 03-Oct-2025
CELL 1.54178 7.572 5.5244 20.5726 90 93.618 90
ZERR 4 0.0002 0.0002 0.0007 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 44 40 8

L.S. 4
PLAN  5 0 0
SIZE 0.1 0.2 0.3
TEMP -153.15
CONF
HTAB
BOND $H
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\cu_ASM599_1_a.hkl">
REM </olex2.extras>

WGHT    0.039600    0.339000
FVAR       1.55754
O1    3    0.264323    0.565202    0.483701    11.00000    0.04333    0.02544 =
         0.02514    0.00682    0.00268   -0.00039
C1    1    0.264523    0.415616    0.526195    11.00000    0.02478    0.02295 =
         0.02137    0.00092    0.00101   -0.00038
O2    3    0.266577    0.472975    0.591081    11.00000    0.03070    0.01582 =
         0.02052    0.00115    0.00167   -0.00001
C2    1    0.264332    0.226905    0.621415    11.00000    0.02000    0.01434 =
         0.02094    0.00198    0.00097    0.00009
C3    1    0.261752    0.243045    0.693602    11.00000    0.01566    0.01915 =
         0.02016   -0.00113    0.00032   -0.00234
C4    1    0.334904    0.055886    0.731898    11.00000    0.02069    0.02079 =
         0.02413   -0.00042    0.00100    0.00108
AFIX  43
H4    2    0.393620   -0.074224    0.712131    11.00000   -1.20000
AFIX   0
C5    1    0.322046    0.059355    0.799058    11.00000    0.02302    0.02828 =
         0.02333    0.00532   -0.00219   -0.00074
AFIX  43
H5    2    0.371053   -0.069324    0.824982    11.00000   -1.20000
AFIX   0
C6    1    0.238157    0.249492    0.828263    11.00000    0.02329    0.03558 =
         0.01868   -0.00181    0.00173   -0.00626
AFIX  43
H6    2    0.228590    0.250561    0.874084    11.00000   -1.20000
AFIX   0
C7    1    0.168126    0.438377    0.790478    11.00000    0.02302    0.02720 =
         0.02669   -0.00643    0.00518   -0.00068
AFIX  43
H7    2    0.112413    0.570346    0.810579    11.00000   -1.20000
AFIX   0
C8    1    0.179131    0.435360    0.723325    11.00000    0.02020    0.02100 =
         0.02510    0.00024    0.00118    0.00131
AFIX  43
H8    2    0.130230    0.564671    0.697613    11.00000   -1.20000
AFIX   0
C9    1    0.402675    0.093853    0.582765    11.00000    0.02347    0.02075 =
         0.02050   -0.00131    0.00177    0.00096
AFIX  23
H9A   2    0.420303   -0.078920    0.594188    11.00000   -1.20000
H9B   2    0.516334    0.180481    0.579788    11.00000   -1.20000
AFIX   0
C10   1    0.261767    0.143423    0.525459    11.00000    0.02722    0.02089 =
         0.01727   -0.00218    0.00086   -0.00103
H10   2    0.261209    0.063512    0.484292    11.00000    0.02610
C11   1    0.120422    0.101716    0.576432    11.00000    0.02265    0.02123 =
         0.02112   -0.00007   -0.00107   -0.00221
AFIX  23
H11A  2    0.009480    0.194954    0.568552    11.00000   -1.20000
H11B  2    0.097651   -0.069935    0.586910    11.00000   -1.20000
AFIX   0
HKLF 4




REM  cu_ASM599_1_a.res in P2(1)/c
REM wR2 = 0.0818, GooF = S = 1.032, Restrained GooF = 1.032 for all data
REM R1 = 0.0328 for 1465 Fo > 4sig(Fo) and 0.0345 for all 1563 data
REM 122 parameters refined using 0 restraints

END

WGHT      0.0396      0.3390

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, -y+1, -z+1
HTAB C9 O1_$1
EQIV $2 -x, -y+1, -z+1
HTAB C11 O1_$2

REM Highest difference peak  0.259,  deepest hole -0.178,  1-sigma level  0.033
Q1    1   0.2643  0.2357  0.6593  11.00000  0.05    0.26
Q2    1   0.1765  0.1716  0.6080  11.00000  0.05    0.24
Q3    1   0.2576  0.2742  0.5209  11.00000  0.05    0.23
Q4    1   0.3468  0.1655  0.6106  11.00000  0.05    0.23
Q5    1   0.3467  0.1090  0.5502  11.00000  0.05    0.21
;
_shelx_res_checksum              40404
_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
O1 O 0.26432(12) 0.56520(16) 0.48370(4) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.26452(15) 0.4156(2) 0.52619(5) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.26658(10) 0.47298(14) 0.59108(4) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.26433(14) 0.22691(19) 0.62141(5) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.26175(13) 0.24304(19) 0.69360(5) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.33490(14) 0.0559(2) 0.73190(5) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.393620 -0.074224 0.712131 0.026 Uiso 1 1 calc R U . . .
C5 C 0.32205(15) 0.0594(2) 0.79906(6) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.371053 -0.069324 0.824982 0.030 Uiso 1 1 calc R U . . .
C6 C 0.23816(15) 0.2495(2) 0.82826(6) 0.0258(3) Uani 1 1 d . . . . .
H6 H 0.228590 0.250561 0.874084 0.031 Uiso 1 1 calc R U . . .
C7 C 0.16813(15) 0.4384(2) 0.79048(6) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.112413 0.570346 0.810579 0.031 Uiso 1 1 calc R U . . .
C8 C 0.17913(14) 0.4354(2) 0.72333(5) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.130230 0.564671 0.697613 0.027 Uiso 1 1 calc R U . . .
C9 C 0.40268(14) 0.0939(2) 0.58276(5) 0.0216(3) Uani 1 1 d . . . . .
H9A H 0.420303 -0.078920 0.594188 0.026 Uiso 1 1 calc R U . . .
H9B H 0.516334 0.180481 0.579788 0.026 Uiso 1 1 calc R U . . .
C10 C 0.26177(15) 0.1434(2) 0.52546(5) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.2612(17) 0.064(3) 0.4843(7) 0.026(3) Uiso 1 1 d . . . . .
C11 C 0.12042(14) 0.1017(2) 0.57643(5) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.009480 0.194954 0.568552 0.026 Uiso 1 1 calc R U . . .
H11B H 0.097651 -0.069935 0.586910 0.026 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 0.0433(5) 0.0254(5) 0.0251(5) 0.0068(4) 0.0027(4) -0.0004(4)
C1 0.0248(6) 0.0230(6) 0.0214(6) 0.0009(5) 0.0010(4) -0.0004(4)
O2 0.0307(4) 0.0158(4) 0.0205(4) 0.0012(3) 0.0017(3) 0.0000(3)
C2 0.0200(5) 0.0143(5) 0.0209(6) 0.0020(4) 0.0010(4) 0.0001(4)
C3 0.0157(5) 0.0191(5) 0.0202(5) -0.0011(4) 0.0003(4) -0.0023(4)
C4 0.0207(5) 0.0208(6) 0.0241(6) -0.0004(4) 0.0010(4) 0.0011(4)
C5 0.0230(6) 0.0283(6) 0.0233(6) 0.0053(5) -0.0022(4) -0.0007(5)
C6 0.0233(6) 0.0356(7) 0.0187(5) -0.0018(5) 0.0017(4) -0.0063(5)
C7 0.0230(5) 0.0272(6) 0.0267(6) -0.0064(5) 0.0052(4) -0.0007(5)
C8 0.0202(5) 0.0210(6) 0.0251(6) 0.0002(4) 0.0012(4) 0.0013(4)
C9 0.0235(5) 0.0207(6) 0.0205(5) -0.0013(4) 0.0018(4) 0.0010(4)
C10 0.0272(6) 0.0209(6) 0.0173(5) -0.0022(4) 0.0009(4) -0.0010(4)
C11 0.0227(5) 0.0212(6) 0.0211(5) -0.0001(4) -0.0011(4) -0.0022(4)
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'
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
O1 C1 O2 123.24(11) . . ?
O1 C1 C10 132.86(11) . . ?
O2 C1 C10 103.90(9) . . ?
C1 O2 C2 101.32(8) . . ?
O2 C2 C9 101.08(8) . . ?
O2 C2 C10 78.47(6) . . ?
O2 C2 C11 100.53(8) . . ?
C3 C2 O2 111.27(8) . . ?
C3 C2 C9 126.53(9) . . ?
C3 C2 C10 170.19(9) . . ?
C3 C2 C11 124.76(9) . . ?
C9 C2 C10 49.74(6) . . ?
C9 C2 C11 87.38(8) . . ?
C11 C2 C10 49.65(6) . . ?
C4 C3 C2 119.32(9) . . ?
C4 C3 C8 119.41(10) . . ?
C8 C3 C2 121.18(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.07(10) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(11) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.84(11) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.24(11) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.14(10) . . ?
C7 C8 H8 119.9 . . ?
C2 C9 H9A 115.0 . . ?
C2 C9 H9B 115.0 . . ?
C2 C9 C10 81.48(8) . . ?
H9A C9 H9B 112.1 . . ?
C10 C9 H9A 115.0 . . ?
C10 C9 H9B 115.0 . . ?
C1 C10 C2 76.31(7) . . ?
C1 C10 C9 99.16(9) . . ?
C1 C10 H10 118.1(8) . . ?
C1 C10 C11 98.65(9) . . ?
C2 C10 H10 165.6(8) . . ?
C9 C10 C2 48.78(6) . . ?
C9 C10 H10 123.5(8) . . ?
C11 C10 C2 49.03(6) . . ?
C11 C10 C9 86.09(8) . . ?
C11 C10 H10 124.2(8) . . ?
C2 C11 C10 81.32(8) . . ?
C2 C11 H11A 115.1 . . ?
C2 C11 H11B 115.1 . . ?
C10 C11 H11A 115.1 . . ?
C10 C11 H11B 115.1 . . ?
H11A C11 H11B 112.1 . . ?
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 1.2029(14) . ?
C1 O2 1.3711(13) . ?
C1 C10 1.5039(16) . ?
O2 C2 1.4963(13) . ?
C2 C3 1.4891(15) . ?
C2 C9 1.5411(14) . ?
C2 C11 1.5475(14) . ?
C3 C4 1.3934(15) . ?
C3 C8 1.3937(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3913(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3842(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3865(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3894(16) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5635(15) . ?
C10 H10 0.955(14) . ?
C10 C11 1.5620(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
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 O2 C2 179.55(11) . . . . ?
O1 C1 C10 C2 -179.54(14) . . . . ?
O1 C1 C10 C9 137.03(13) . . . . ?
O1 C1 C10 C11 -135.56(13) . . . . ?
C1 O2 C2 C3 -178.66(8) . . . . ?
C1 O2 C2 C9 44.70(9) . . . . ?
C1 O2 C2 C10 0.10(7) . . . . ?
C1 O2 C2 C11 -44.66(9) . . . . ?
C1 C10 C11 C2 -63.31(9) . . . . ?
O2 C1 C10 C2 0.10(7) . . . . ?
O2 C1 C10 C9 -43.33(10) . . . . ?
O2 C1 C10 C11 44.07(10) . . . . ?
O2 C2 C3 C4 -152.05(9) . . . . ?
O2 C2 C3 C8 31.45(13) . . . . ?
O2 C2 C9 C10 -64.36(8) . . . . ?
O2 C2 C11 C10 64.87(8) . . . . ?
C2 C3 C4 C5 -175.25(10) . . . . ?
C2 C3 C8 C7 175.71(10) . . . . ?
C2 C9 C10 C1 62.62(9) . . . . ?
C2 C9 C10 C11 -35.53(8) . . . . ?
C3 C2 C9 C10 168.41(11) . . . . ?
C3 C2 C11 C10 -169.82(10) . . . . ?
C3 C4 C5 C6 -0.61(17) . . . . ?
C4 C3 C8 C7 -0.79(16) . . . . ?
C4 C5 C6 C7 -0.61(17) . . . . ?
C5 C6 C7 C8 1.13(17) . . . . ?
C6 C7 C8 C3 -0.43(16) . . . . ?
C8 C3 C4 C5 1.30(16) . . . . ?
C9 C2 C3 C4 -29.03(15) . . . . ?
C9 C2 C3 C8 154.47(11) . . . . ?
C9 C2 C11 C10 -35.91(8) . . . . ?
C9 C10 C11 C2 35.37(7) . . . . ?
C10 C1 O2 C2 -0.14(10) . . . . ?
C11 C2 C3 C4 87.37(13) . . . . ?
C11 C2 C3 C8 -89.13(13) . . . . ?
C11 C2 C9 C10 35.86(8) . . . . ?