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_7131172
_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         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_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.cc2cym65
_audit_creation_date             2022-07-19
_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                90
_cell_angle_beta                 101.7637(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.41961(18)
_cell_length_b                   5.65053(12)
_cell_length_c                   19.2947(3)
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3270
_cell_measurement_theta_min      3.9650
_cell_volume                     1218.88(4)
_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      100.01(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    -60.00 -35.00   0.50    0.05    --  -59.16 136.00 -16.00   50
  2  \w    -67.00 -42.00   0.50    0.05    --  -59.16 134.00 164.00   50
  3  \w   -106.00 -65.00   0.50    0.05    --  -72.12 136.00 -16.00   82
  4  \w    -89.00 -64.00   0.50    0.05    --  -72.12 134.00 164.00   50
  5  \w    -67.00 -28.00   0.50    0.05    --  -75.04 136.00 -16.00   78
  6  \w     29.00  54.00   0.50    0.05    --   75.69-134.00  97.00   50
  7  \w     43.00  68.00   0.50    0.05    --   75.69-136.00 -81.00   50
  8  \w     37.00  77.00   0.50    0.05    --   83.90-136.00 -81.00   80
  9  \w     38.00  78.00   0.50    0.05    --   83.90-134.00  97.00   80
 10  \w     17.00  43.00   0.50    0.05    --   56.22 -95.00 -60.00   52
 11  \w     37.00  89.00   0.50    0.05    --   56.22  15.00-180.00  104
 12  \w   -106.00 -70.00   0.50    0.05    --  -59.16 -15.00-180.00   72
 13  \w    -67.00 -42.00   0.50    0.05    --  -59.16 -15.00 -30.00   50
 14  \w   -100.00 -74.00   0.50    0.05    --  -59.16 -15.00 -30.00   52
 15  \w    -63.00 -38.00   0.50    0.05    --  -59.16 -15.00-180.00   50
 16  \w    -58.00 -27.00   0.50    0.05    --  -75.04 111.00 -30.00   62
 17  \w   -118.00 -52.00   0.50    0.05    --  -75.04 -15.00  60.00  132
 18  \w     30.00  92.00   0.50    0.05    --   75.69-111.00-150.00  124
 19  \w     37.00  77.00   0.50    0.05    --   75.69 -95.00 120.00   80
 20  \w     43.00  92.00   0.50    0.05    --   83.90 -95.00 -60.00   98
 21  \w     60.00  91.00   0.50    0.05    --   83.90 -95.00  90.00   62
 22  \w     67.00  92.00   0.50    0.05    --   83.90 -95.00-150.00   50
 23  \w     67.00  92.00   0.50    0.05    --   83.90 -95.00  30.00   50
 24  \w     36.00  93.00   0.50    0.05    --   83.90-111.00  30.00  114
 25  \w     66.00  91.00   0.50    0.05    --   83.90 -95.00 -90.00   50
 26  \w     58.00 134.00   0.50    0.05    --   83.90  15.00-150.00  152
;
_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      0.0338702000
_diffrn_orient_matrix_UB_12      -0.1783031000
_diffrn_orient_matrix_UB_13      -0.0530276000
_diffrn_orient_matrix_UB_21      0.0301705000
_diffrn_orient_matrix_UB_22      0.2062062000
_diffrn_orient_matrix_UB_23      -0.0455630000
_diffrn_orient_matrix_UB_31      0.1301446000
_diffrn_orient_matrix_UB_32      -0.0014090000
_diffrn_orient_matrix_UB_33      0.0419971000
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8591
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.954
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98500
_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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0022(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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0355P)^2^+0.4606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1997
_reflns_number_total             2167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05912f2.cif
_cod_data_source_block           220747lt_auto
_cod_depositor_comments
'Adding full bibliography for 7131170--7131173.cif.'
_cod_database_code               7131172
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.917
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_shelx_res_checksum              33276
_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 1.059
_oxdiff_exptl_absorpt_empirical_full_min 0.917