Synthesis of functionalized lactones: catalytic cross-coupling of 1,2-diols and allylic alcohols.
Maharana, Priyanka; Sankar, Raman Vijaya; Sankaralingam, Muniyandi; Gunanathan, Chidambaram; Chemical communications (Cambridge, England) 61 (2025) 11947–11950; doi:10.1039/d5cc02207j

data_7134772
_publ_section_title
;
 Synthesis of functionalized lactones: catalytic cross-coupling of
 1,2-diols and allylic alcohols.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11947
_journal_page_last               11950
_journal_paper_doi               10.1039/d5cc02207j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C27 H20 O3'
_chemical_formula_sum            'C27 H20 O3'
_chemical_formula_weight         392.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-16 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.838(4)
_cell_angle_beta                 107.111(4)
_cell_angle_gamma                99.692(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4872(4)
_cell_length_b                   10.3122(5)
_cell_length_c                   11.7926(5)
_cell_measurement_reflns_used    8014
_cell_measurement_temperature    295.1(4)
_cell_measurement_theta_max      77.8590
_cell_measurement_theta_min      3.9280
_cell_volume                     956.65(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.1(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.907
_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   -106.00 -36.08   0.38    0.29    --  -38.50 -33.00  22.00  184
  2  \w    -42.00  27.92   0.38    0.29    --  -38.50  33.00-179.00  184
  3  \w    -18.00  50.78   0.38    0.29    --   49.06 -33.00  22.00  181
  4  \w     46.00 115.92   0.38    0.29    --   49.06  33.00-179.00  184
  5  \w     40.00 109.92   0.38    1.06    --  107.46 -33.00  22.00  184
  6  \w    104.00 173.92   0.38    1.06    --  107.46  33.00-179.00  184
  7  \w    -42.00  26.78   0.38    0.29    --  -38.50  37.00 -60.00  181
  8  \w    -86.00  -7.34   0.38    0.29    --  -38.50 125.00-120.00  207
  9  \w    -50.00  22.96   0.38    0.29    --  -38.50  57.00 150.00  192
 10  \w   -105.00 -36.22   0.38    0.29    --  -38.50 -37.00   0.00  181
 11  \w     28.00  96.78   0.38    0.29    --   49.06-125.00 -60.00  181
 12  \w     43.00 110.64   0.38    1.06    --  107.46 -45.00 -90.00  178
 13  \w     45.00 111.88   0.38    1.06    --  107.46-125.00-150.00  176
 14  \w     45.00 111.88   0.38    1.06    --  107.46-125.00  90.00  176
 15  \w     97.00 168.82   0.38    1.06    --  107.46 125.00-150.00  189
 16  \w     39.00 105.88   0.38    1.06    --  107.46 -94.00 -30.00  176
 17  \w     99.00 175.00   0.38    1.06    --  107.46  15.00   0.00  200
 18  \w     43.00 110.64   0.38    1.06    --  107.46 -45.00 150.00  178
 19  \w    103.00 170.64   0.38    1.06    --  107.46  45.00  30.00  178
 20  \w     45.00 121.00   0.38    1.06    --  107.46 -61.00-120.00  200
 21  \w     43.00 110.64   0.38    1.06    --  107.46 -45.00 -30.00  178
 22  \w     39.00 105.88   0.38    1.06    --  107.46 -94.00-180.00  176
 23  \w     39.00 115.00   0.38    1.06    --  107.46 -15.00  30.00  200
 24  \w     39.00 109.68   0.38    1.06    --  107.46 -30.00-150.00  186
 25  \w     45.00 121.00   0.38    1.06    --  107.46 -61.00  60.00  200
 26  \w    103.00 170.64   0.38    1.06    --  107.46  45.00-150.00  178
 27  \w     39.00 105.88   0.38    1.06    --  107.46 -94.00-150.00  176
 28  \w     39.00 105.88   0.38    1.06    --  107.46 -94.00  30.00  176
 29  \w    103.00 170.64   0.38    1.06    --  107.46  77.00 -60.00  178
 30  \w     39.00 105.88   0.38    1.06    --  107.46 -94.00  90.00  176
 31  \w     43.00 129.64   0.38    1.06    --  107.46 -77.00-180.00  228
 32  \w     38.00 110.96   0.38    0.29    --   49.06  57.00 120.00  192
 33  \w     38.00 110.96   0.38    0.29    --   49.06  57.00-150.00  192
 34  \w     32.00 110.66   0.38    0.29    --   49.06  67.00 -43.28  207
 35  \w     34.00 110.76   0.38    0.29    --   49.06  64.00  49.73  202
 36  \w     38.00 110.96   0.38    0.29    --   49.06  57.00 -90.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1576393000
_diffrn_orient_matrix_UB_12      0.0512216000
_diffrn_orient_matrix_UB_13      0.0075015000
_diffrn_orient_matrix_UB_21      -0.1106297000
_diffrn_orient_matrix_UB_22      -0.1402186000
_diffrn_orient_matrix_UB_23      -0.0586435000
_diffrn_orient_matrix_UB_31      0.0267978000
_diffrn_orient_matrix_UB_32      -0.0379983000
_diffrn_orient_matrix_UB_33      0.1257236000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12861
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         86.175
_diffrn_reflns_theta_min         3.987
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_preparation       'as per reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0024(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0836P)^2^+0.0783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             3929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02207j2.cif
_cod_data_source_block           cg_pm_194_auto
_cod_depositor_comments          'Adding full bibliography for 7134772.cif.'
_cod_original_cell_volume        956.66(8)
_cod_database_code               7134772
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.861
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              64982
_shelx_hkl_checksum              58737
_olex2_exptl_crystal_mounting_method 'Mounted on a loop'
_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 4.565
_oxdiff_exptl_absorpt_empirical_full_min 0.479