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_7158491
_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_formula_moiety         'C31 H21 N O2'
_chemical_formula_sum            'C31 H21 N O2'
_chemical_formula_weight         439.49
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-05-08 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.780(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.98540(10)
_cell_length_b                   20.6879(4)
_cell_length_c                   18.0213(3)
_cell_measurement_reflns_used    16095
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9560
_cell_measurement_theta_min      1.9680
_cell_volume                     2220.15(7)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_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    -20.00 100.00   0.50    8.65    --   10.60  57.00 -60.00  240
  2  \w    -20.00 100.00   0.50    8.65    --   10.60  57.00 120.00  240
  3  \w    -15.00 100.00   0.50    8.65    --   10.60  77.00 -60.00  230
  4  \w    -79.00  38.00   0.50    8.65    --   10.60 -82.00 -30.00  234
  5  \w   -100.00  15.00   0.50    8.65    --  -10.90 -77.00   0.00  230
  6  \w    -30.00  20.00   0.50    8.65    --  -10.90 -57.00  30.00  100
  7  \w     16.00  52.00   0.50    8.65    --  -10.90  38.00 -60.00   72
;
_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      0.1051128000
_diffrn_orient_matrix_UB_12      -0.0146274000
_diffrn_orient_matrix_UB_13      -0.0042411000
_diffrn_orient_matrix_UB_21      -0.0560461000
_diffrn_orient_matrix_UB_22      -0.0269721000
_diffrn_orient_matrix_UB_23      -0.0176421000
_diffrn_orient_matrix_UB_31      0.0018124000
_diffrn_orient_matrix_UB_32      0.0153083000
_diffrn_orient_matrix_UB_33      -0.0351434000
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.035
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80812
_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    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0446P)^2^+0.5723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4037
_reflns_number_total             4684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02290c2.cif
_cod_data_source_block           k11004-jjw-d
_cod_depositor_comments
'Adding full bibliography for 7158490--7158491.cif.'
_cod_database_code               7158491
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01b1b68829f8b2d8d65156215ba76a75e6000258f9a
;
_diffrn_oxdiff_digest_hkl
;
01b80ea9874e6197b47a0f2205edb0d23cd341
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
;
_shelx_res_checksum              26528
_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.812