A metal-free strategy for the cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol.
Kudale, Vishal Suresh; Zheng, Sheng; Huang, Sheng-Hua; Chang, Yu-Lun; Wang, Jeh-Jeng; Organic & biomolecular chemistry 20 (2022) 1226–1230; doi:10.1039/d1ob02290c

data_7158490
_publ_section_title
;
 A metal-free strategy for the cross-dehydrogenative coupling of
 1,3-dicarbonyl compounds with 2-methoxyethanol.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1226
_journal_page_last               1230
_journal_paper_doi               10.1039/d1ob02290c
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C31 H22 F2 O4'
_chemical_formula_sum            'C31 H22 F2 O4'
_chemical_formula_weight         496.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2021-05-08 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.580(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8605(5)
_cell_length_b                   11.7131(10)
_cell_length_c                   13.7225(7)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      26.5040
_cell_measurement_theta_min      2.2750
_cell_volume                     1259.41(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -15.00 100.00   0.50   13.63    --   10.60  77.00   0.00  230
  2  \w    -79.00  36.00   0.50   13.63    --   10.60 -77.00 120.00  230
  3  \w    -79.00  41.00   0.50   13.63    --   10.60 -57.00 -90.00  240
  4  \w    -15.00 100.00   0.50   13.63    --   10.60  77.00-180.00  230
  5  \w    -79.00  41.00   0.50   13.63    --   10.60 -57.00-120.00  240
  6  \w    -17.00 100.00   0.50   13.63    --   10.60  82.00  60.00  234
  7  \w    -79.00  41.00   0.50   13.63    --   10.60 -57.00   0.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II 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      0.0686750000
_diffrn_orient_matrix_UB_12      -0.0162300000
_diffrn_orient_matrix_UB_13      -0.0277134000
_diffrn_orient_matrix_UB_21      -0.0457944000
_diffrn_orient_matrix_UB_22      0.0212102000
_diffrn_orient_matrix_UB_23      -0.0429828000
_diffrn_orient_matrix_UB_31      0.0372668000
_diffrn_orient_matrix_UB_32      0.0543387000
_diffrn_orient_matrix_UB_33      0.0085301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16457
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.289
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.0
_exptl_crystal_size_min          0.0
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.7(14)
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     955
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0534
_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^)+(0.1032P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3603
_reflns_number_total             4297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02290c2.cif
_cod_data_source_block           k11005-jjw-b
_cod_depositor_comments
'Adding full bibliography for 7158490--7158491.cif.'
_cod_database_code               7158490
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.7(14)
 -0.7(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim O1 \\sim O2
\\sim O3 \\sim O4 \\sim F1 \\sim F2: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
4.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              11930
_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 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.505