Catalyst-free diazo cross-coupling to access useful 3(2<i>H</i>)-furanone derivatives.
Sasane, Amit Vijay; Liu, Rai-Shung; Chemical communications (Cambridge, England) 59 (2023) 1086–1089; doi:10.1039/d2cc05912f

data_7131173
_publ_section_title
;
 Catalyst-free diazo cross-coupling to access useful 3(2<i>H</i>)-furanone
 derivatives.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1086
_journal_page_last               1089
_journal_paper_doi               10.1039/d2cc05912f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C17 H18 O2'
_chemical_formula_sum            'C17 H18 O2'
_chemical_formula_weight         254.31
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2cymb9
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                75.901(3)
_cell_angle_beta                 80.614(3)
_cell_angle_gamma                79.208(3)
_cell_formula_units_Z            4
_cell_length_a                   5.94355(19)
_cell_length_b                   13.5482(4)
_cell_length_c                   17.6441(5)
_cell_measurement_reflns_used    6300
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.3060
_cell_measurement_theta_min      2.5980
_cell_volume                     1343.28(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -55.00 -16.00   0.50    0.65    --  -59.30 125.00 -30.00   78
  2  \w    -52.00 -20.00   0.50    0.65    --  -59.30 119.00 -71.00   64
  3  \w    -60.00 -34.00   0.50    0.65    --  -72.08 119.00 -71.00   52
  4  \w    -98.00 -66.00   0.50    0.65    --  -75.84 119.00 -71.00   64
  5  \w    -97.00 -71.00   0.50    0.65    --  -80.37 115.00-108.65   52
  6  \w   -103.00 -54.00   0.50    0.65    --  -72.08 -15.00  60.00   98
  7  \w   -121.00 -40.00   0.50    0.65    --  -75.84 -15.00  30.00  162
  8  \w   -125.00 -46.00   0.50    0.65    --  -75.84 -15.00 -60.00  158
  9  \w    -89.00 -36.00   0.50    0.65    --  -72.08 -15.00-150.00  106
 10  \w     16.00  47.00   0.50    0.65    --   56.16-119.00-156.00   62
 11  \w     38.00  63.00   0.50    0.65    --   76.45-119.00-156.00   50
 12  \w     21.00  84.00   0.50    0.65    --   69.22-119.00-156.00  126
 13  \w     38.00  63.00   0.50    0.65    --   84.29-111.00-120.00   50
 14  \w     42.00  67.00   0.50    0.65    --   84.29-119.00-156.00   50
 15  \w     29.00  78.00   0.50    0.65    --   76.45-111.00 -90.00   98
 16  \w     37.00  62.00   0.50    0.65    --   84.29-111.00 -30.00   50
 17  \w     34.00  60.00   0.50    0.65    --   76.45 -95.00 -60.00   52
 18  \w     36.00  73.00   0.50    0.65    --   76.45 -95.00   0.00   74
 19  \w     41.00  67.00   0.50    0.65    --   76.45-111.00  90.00   52
 20  \w     44.00  85.00   0.50    0.65    --   84.29-111.00 150.00   82
 21  \w     21.00  48.00   0.50    0.65    --   56.16 -95.00 120.00   54
 22  \w     13.00  38.00   0.50    0.65    --   56.16 -95.00  90.00   50
 23  \w     67.00  92.00   0.50    0.65    --   84.29 -95.00  60.00   50
 24  \w     59.00  92.00   0.50    0.65    --   84.29 -95.00  90.00   66
 25  \w     44.00  92.00   0.50    0.65    --   84.29 -95.00  30.00   96
 26  \w     50.00  92.00   0.50    0.65    --   84.29 -95.00 -30.00   84
 27  \w     65.00  90.00   0.50    0.65    --   84.29 -95.00 -60.00   50
 28  \w     42.00  67.00   0.50    0.65    --   84.29 -95.00 -90.00   50
 29  \w     66.00  92.00   0.50    0.65    --   84.29 -95.00-150.00   52
 30  \w     63.00  91.00   0.50    0.65    --   84.29 -95.00-180.00   56
 31  \w     13.00  64.00   0.50    0.65    --   56.16 -95.00-120.00  102
 32  \w     40.00  79.00   0.50    0.65    --   76.45 -95.00  90.00   78
 33  \w     34.00  82.00   0.50    0.65    --   76.45 -95.00 150.00   96
 34  \w     48.00 134.00   0.50    0.65    --   84.29  15.00 -30.00  172
 35  \w     49.00 107.00   0.50    0.65    --   84.29  15.00 -90.00  116
 36  \w     51.00  76.00   0.50    0.65    --   84.29  15.00-120.00   50
 37  \w     43.00 107.00   0.50    0.65    --   56.16  15.00-120.00  128
 38  \w     49.00 113.00   0.50    0.65    --   84.29  15.00  90.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0857516000
_diffrn_orient_matrix_UB_12      0.1133528000
_diffrn_orient_matrix_UB_13      -0.0371513000
_diffrn_orient_matrix_UB_21      0.1080914000
_diffrn_orient_matrix_UB_22      -0.0181806000
_diffrn_orient_matrix_UB_23      -0.0819084000
_diffrn_orient_matrix_UB_31      -0.2272949000
_diffrn_orient_matrix_UB_32      -0.0300113000
_diffrn_orient_matrix_UB_33      -0.0118506000
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15811
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         2.602
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0018(3)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0554P)^2^+0.3602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3945
_reflns_number_total             4759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05912f2.cif
_cod_data_source_block           220784lt_auto
_cod_depositor_comments
;
Adding full bibliography for 7131170--7131173.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H36 O4'
_cod_original_formula_weight         508.63
_cod_original_formula_moiety         '2(C17 H18 O2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1343.28(8)
_cod_database_code               7131173
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O18(H18), O37(H37)
;
_shelx_res_checksum              68205
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.711