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_7131171
_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         'C28 H23 N O2'
_chemical_formula_sum            'C28 H23 N O2'
_chemical_formula_weight         405.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-31 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.66639(16)
_cell_length_b                   17.3063(2)
_cell_length_c                   18.4966(2)
_cell_measurement_reflns_used    10834
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      74.5060
_cell_measurement_theta_min      4.7470
_cell_volume                     4374.72(9)
_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      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  75.00   0.50    2.00    --   56.16-125.00-150.00  110
  2  \w     44.00  71.00   0.50    2.00    --   84.29-111.00 -90.00   54
  3  \w     13.00  39.00   0.50    2.00    --   56.16 -95.00 -30.00   52
  4  \w     34.00  68.00   0.50    2.00    --   76.45 -95.00  30.00   68
  5  \w     32.00  57.00   0.50    2.00    --   69.22 -95.00  60.00   50
  6  \w     43.00  89.00   0.50    2.00    --   84.29-111.00  60.00   92
  7  \w     29.00  54.00   0.50    2.00    --   56.16 -95.00 -90.00   50
  8  \w     41.00  81.00   0.50    2.00    --   76.45 -95.00-180.00   80
  9  \w     58.00  84.00   0.50    2.00    --   76.45 -95.00-150.00   52
 10  \w     56.00  82.00   0.50    2.00    --   84.29 -95.00 -90.00   52
 11  \w     13.00  45.00   0.50    2.00    --   56.16 -95.00  30.00   64
 12  \w     41.00 114.00   0.50    2.00    --   76.45  15.00 -30.00  146
 13  \w     49.00 131.00   0.50    2.00    --   84.29  15.00-120.00  164
 14  \w     50.00 133.00   0.50    2.00    --   84.29  15.00 150.00  166
 15  \w   -105.00 -65.00   0.50    2.00    --  -75.84 -15.00 -90.00   80
 16  \w   -126.00 -41.00   0.50    2.00    --  -75.84 -15.00 -30.00  170
 17  \w    -55.00 -30.00   0.50    2.00    --  -72.08 125.00  90.00   50
 18  \w    -78.00 -34.00   0.50    2.00    --  -75.84 111.00 -90.00   88
 19  \w    -51.00 -14.00   0.50    2.00    --  -59.30 125.00-180.00   74
;
_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      0.0785115000
_diffrn_orient_matrix_UB_12      -0.0398803000
_diffrn_orient_matrix_UB_13      -0.0466904000
_diffrn_orient_matrix_UB_21      0.0234553000
_diffrn_orient_matrix_UB_22      -0.0552724000
_diffrn_orient_matrix_UB_23      0.0629238000
_diffrn_orient_matrix_UB_31      -0.0774801000
_diffrn_orient_matrix_UB_32      -0.0572111000
_diffrn_orient_matrix_UB_33      -0.0282310000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.766
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85008
_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    1.231
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.00049(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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0372P)^2^+1.1436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3473
_reflns_number_total             3913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05912f2.cif
_cod_data_source_block           2210100lt_auto
_cod_depositor_comments
'Adding full bibliography for 7131170--7131173.cif.'
_cod_original_cell_volume        4374.70(9)
_cod_database_code               7131171
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              86233
_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.860