Electrocatalytic ring-opening dihydroalkoxylation of <i>N</i>-aryl maleimides with alcohols under metal- and oxidant-free conditions.
Zhang, Zhang; Wang, Ying-Chun; Tang, Hai-Tao; Pan, Ying-Ming; Meng, Xiu-Jin; Organic & biomolecular chemistry 21 (2023) 3177–3182; doi:10.1039/d3ob00178d

data_7159249
_publ_section_title
;
 Electrocatalytic ring-opening dihydroalkoxylation of <i>N</i>-aryl
 maleimides with alcohols under metal- and oxidant-free conditions.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3177
_journal_page_last               3182
_journal_paper_doi               10.1039/d3ob00178d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d6dvw
_audit_creation_date             2022-08-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-02 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.192(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.340(4)
_cell_length_b                   5.3646(6)
_cell_length_c                   10.6018(13)
_cell_measurement_reflns_used    835
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      70.4320
_cell_measurement_theta_min      3.2380
_cell_volume                     1550.8(3)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     -2.00 124.00   0.50    0.50    --   41.80   0.00 120.00  252
  2  \w    -15.00  60.00   0.50    0.50    --   41.80 -57.00  90.00  150
  3  \w     84.00 110.00   0.50    0.50    --   41.80  77.00 120.00   52
  4  \w     38.00 134.00   0.50    1.00    --  102.30 -50.00-150.00  192
  5  \w     56.00 172.00   0.50    1.00    --  102.30  38.00   0.00  232
  6  \w     25.00  74.00   0.50    1.00    --  102.30 -64.00-150.00   98
  7  \w     66.00  92.00   0.50    1.00    --  102.30 -77.00 -60.00   52
  8  \w     14.00  40.00   0.50    1.00    --  102.30 -77.00  60.00   52
  9  \w     47.00 142.00   0.50    1.00    --  102.30 -77.00  60.00  190
 10  \w     83.00 121.00   0.50    1.00    --  102.30 -64.00-150.00   76
 11  \w     90.00 136.00   0.50    1.00    --  102.30  82.00 -30.00   92
 12  \w     14.00 126.00   0.50    1.00    --  102.30 -64.00  60.00  224
;
_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      0.0516080000
_diffrn_orient_matrix_UB_12      -0.0200079000
_diffrn_orient_matrix_UB_13      0.0679970000
_diffrn_orient_matrix_UB_21      -0.0223293000
_diffrn_orient_matrix_UB_22      -0.1091335000
_diffrn_orient_matrix_UB_23      0.1173032000
_diffrn_orient_matrix_UB_31      0.0053641000
_diffrn_orient_matrix_UB_32      -0.2647989000
_diffrn_orient_matrix_UB_33      -0.0534681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5702
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.242
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63480
_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_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.1125
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2955
_refine_ls_wR_factor_ref         0.3212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00178d2.cif
_cod_data_source_block           b-0817
_cod_depositor_comments          'Adding full bibliography for 7159249.cif.'
_cod_database_code               7159249
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11),
 C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              71077
_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 2.061
_oxdiff_exptl_absorpt_empirical_full_min 0.488