Anodic Oxidation Triggered Divergent 1,2- and 1,4-Group Transfer Reactions of β-Hydroxycarboxylic Acids Enabled by Electrochemical Regulation
Zhang, Zhenxing; Zhang, Lei; Zhang, Xianhao; Yang, Jianxin; Yin, Yunxing; Jiang, Yangye; Zeng, Cheng-Chu; Lu, Gang; Yang, Yang; Mo, Fanyang; Chemical Science  (2020) –; doi:10.1039/D0SC02386H

data_1559215
_publ_section_title
;
 Anodic Oxidation Triggered Divergent 1,2- and 1,4-Group Transfer
 Reactions of \b-Hydroxycarboxylic Acids Enabled by Electrochemical
 Regulation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02386H
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 O3'
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-02 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.032(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0221(2)
_cell_length_b                   11.8060(3)
_cell_length_c                   13.2172(3)
_cell_measurement_reflns_used    18511
_cell_measurement_temperature    179.97(18)
_cell_measurement_theta_max      30.7360
_cell_measurement_theta_min      3.1450
_cell_volume                     1224.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.97(18)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     42.00  81.00   0.50    1.00    --   -1.90  57.00 150.00   78
  2  \w    -21.00  88.00   0.50    1.00    --   -1.90  37.00-150.00  218
  3  \w    -25.00  84.00   0.50    1.00    --   -1.90  57.00  60.00  218
  4  \w     48.00  88.00   0.50    1.00    --   -1.90  19.00 150.00   80
  5  \w    -25.00  17.00   0.50    1.00    --   -1.90  57.00 150.00   84
  6  \w    -26.00  88.00   0.50    1.00    --   -1.90  19.00   0.00  228
  7  \w    -26.00  42.00   0.50    1.00    --   -1.90  19.00 150.00  136
  8  \w      9.00  34.00   0.50    1.00    --    2.00 -82.00 120.00   50
  9  \w    -32.00  -4.00   0.50    1.00    --    2.00 -82.00 120.00   56
 10  \w    -33.00  34.00   0.50    1.00    --    2.00 -82.00  30.00  134
 11  \w      9.00  34.00   0.50    1.00    --    2.00 -82.00 -90.00   50
 12  \w    -32.00  -5.00   0.50    1.00    --    2.00 -82.00 -90.00   54
 13  \w      2.00  34.00   0.50    1.00    --    2.00 -82.00 -30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0244211000
_diffrn_orient_matrix_UB_12      -0.0518355000
_diffrn_orient_matrix_UB_13      -0.0197760000
_diffrn_orient_matrix_UB_21      -0.0565292000
_diffrn_orient_matrix_UB_22      -0.0296587000
_diffrn_orient_matrix_UB_23      0.0252908000
_diffrn_orient_matrix_UB_31      -0.0662424000
_diffrn_orient_matrix_UB_32      0.0061967000
_diffrn_orient_matrix_UB_33      -0.0445154000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35463
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.418
_diffrn_reflns_theta_min         2.742
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0533P)^2^+0.3973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3122
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02386h2.cif
_cod_data_source_block           exp_2935
_cod_database_code               1559215
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C16H12O3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.644