A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans.
Bennett, Ryan M.; Sun, Wei; Wilson, Dharyl C.; Light, Mark E.; Harrowven, David C.; Chemical communications (Cambridge, England) 57 (2021) 5694–5697; doi:10.1039/d1cc02097h

data_7128289
_publ_section_title
;
 A new mode of cyclobutenedione ring opening for the synthesis of
 2-oxobut-3-enamides and tetrasubstituted furans.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5694
_journal_page_last               5697
_journal_paper_doi               10.1039/d1cc02097h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C16 H30 N2 O3'
_chemical_formula_sum            'C16 H30 N2 O3'
_chemical_formula_weight         298.42
_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
_audit_creation_date             2021-01-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-28 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                70.260(4)
_cell_angle_beta                 88.043(4)
_cell_angle_gamma                78.758(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0189(3)
_cell_length_b                   10.6268(6)
_cell_length_c                   14.7651(6)
_cell_measurement_reflns_used    6867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7840
_cell_measurement_theta_min      2.0600
_cell_volume                     871.33(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -56.00  63.00   0.50    5.00    --  -13.40  43.00-150.63  238
  2  \w   -100.00 -30.00   0.50    5.00    --  -13.40 -19.00 -60.00  140
  3  \w     -4.00  58.00   0.50    5.00    --  -13.40 -19.00 -60.00  124
  4  \w    -87.00  -1.00   0.50    5.00    --  -13.40 -60.00-180.00  172
  5  \w    -67.00  22.00   0.50    5.00    --  -13.40 -60.00  30.00  178
  6  \w    -49.00 -16.00   0.50    5.00    --  -13.40  57.00 -60.00   66
  7  \w    -12.00  35.00   0.50    5.00    --  -13.40  57.00 -60.00   94
  8  \w     38.00  73.00   0.50    5.00    --  -13.40  57.00 -60.00   70
  9  \w   -102.00   6.00   0.50    5.00    --  -13.40 -60.00 -90.00  216
 10  \w    -49.00  71.00   0.50    5.00    --  -13.40  60.00  90.00  240
 11  \w    -55.00  -5.00   0.50    5.00    --  -13.40  44.00  11.06  100
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207968000
_diffrn_orient_matrix_UB_12      0.0694041000
_diffrn_orient_matrix_UB_13      -0.0031379000
_diffrn_orient_matrix_UB_21      0.0075442000
_diffrn_orient_matrix_UB_22      -0.0202430000
_diffrn_orient_matrix_UB_23      0.0509315000
_diffrn_orient_matrix_UB_31      0.1181694000
_diffrn_orient_matrix_UB_32      -0.0008355000
_diffrn_orient_matrix_UB_33      -0.0020197000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of diethyl ether and hexane  by slow evaporation'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0634
_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^)+(0.0744P)^2^+0.0199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3425
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02097h2.cif
_cod_data_source_block           2020sot0037_r1_100k
_cod_depositor_comments
'Adding full bibliography for 7128287--7128289.cif.'
_cod_database_code               7128289
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H30N2O3
_chemical_oxdiff_usercomment     rb/9071/23.61p
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_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:
 C11(H11), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              53617
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id rb/9071/23.61p
_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 4.011
_oxdiff_exptl_absorpt_empirical_full_min 0.254