Stereo- and Regiocontrol in Intermolecular [2+2] Cycloadditions between Diarylketenes and Allenamides to Access Substituted α-Methylenecyclobutanones.
Liu, Rai-Shung; Kshirsagar, Akshay Suresh; More, Sayaji Arjun; Chemical Communications  (2023) –; doi:10.1039/D3CC03979J

data_7132118
_publ_section_title
;
 Stereo- and Regiocontrol in Intermolecular [2+2] Cycloadditions between
 Diarylketenes and Allenamides to Access Substituted
 \a-Methylenecyclobutanones.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03979J
_journal_year                    2023
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_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             2022-06-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.86145(10)
_cell_length_b                   18.8062(2)
_cell_length_c                   19.06566(19)
_cell_measurement_reflns_used    15262
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6670
_cell_measurement_theta_min      4.6270
_cell_volume                     3177.30(6)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 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    -77.00 -35.00   0.50    0.05    --  -59.30 -15.00-150.00   84
  2  \w   -126.00 -41.00   0.50    0.05    --  -76.01 -15.00 -30.00  170
  3  \w    -69.00 -44.00   0.50    0.05    --  -59.30 112.00 -54.00   50
  4  \w    -72.00 -29.00   0.50    0.05    --  -76.01 112.00 -54.00   86
  5  \w    -91.00 -34.00   0.50    0.05    --  -76.01 111.00  90.00  114
  6  \w    -82.00 -57.00   0.50    0.05    --  -71.94 112.00 -54.00   50
  7  \w     36.00  67.00   0.50    0.05    --   69.43  15.00-180.00   62
  8  \w     88.00 119.00   0.50    0.05    --   69.43  15.00-180.00   62
  9  \w     55.00 130.00   0.50    0.05    --   84.37  15.00 -90.00  150
 10  \w     48.00 113.00   0.50    0.05    --   76.52  15.00 -30.00  130
 11  \w     49.00 109.00   0.50    0.05    --   84.37  15.00  30.00  120
 12  \w     47.00  92.00   0.50    0.05    --   84.37 -95.00 -90.00   90
 13  \w     12.00  65.00   0.50    0.05    --   56.31-112.00-147.00  106
 14  \w     21.00  75.00   0.50    0.05    --   69.43-112.00-147.00  108
 15  \w     45.00  70.00   0.50    0.05    --   76.52-112.00-147.00   50
 16  \w     40.00  65.00   0.50    0.05    --   84.37-112.00-147.00   50
 17  \w     53.00  80.00   0.50    0.05    --   76.52 -95.00-120.00   54
 18  \w     32.00  91.00   0.50    0.05    --   76.52-111.00 -30.00  118
 19  \w     27.00  52.00   0.50    0.05    --   69.43 -95.00  30.00   50
 20  \w     47.00  72.00   0.50    0.05    --   84.37-111.00 120.00   50
 21  \w     32.00  58.00   0.50    0.05    --   56.31 -95.00 120.00   52
 22  \w     47.00  89.00   0.50    0.05    --   84.37 -95.00  30.00   84
 23  \w     65.00  90.00   0.50    0.05    --   84.37 -95.00-120.00   50
 24  \w     44.00  92.00   0.50    0.05    --   84.37 -95.00-150.00   96
;
_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      0.1634891000
_diffrn_orient_matrix_UB_12      0.0157321000
_diffrn_orient_matrix_UB_13      0.0227023000
_diffrn_orient_matrix_UB_21      -0.0213775000
_diffrn_orient_matrix_UB_22      0.0788029000
_diffrn_orient_matrix_UB_23      -0.0197304000
_diffrn_orient_matrix_UB_31      -0.0551004000
_diffrn_orient_matrix_UB_32      0.0159851000
_diffrn_orient_matrix_UB_33      0.0749834000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23337
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.639
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96188
_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    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00100(9)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0345P)^2^+1.6170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2685
_reflns_number_total             2834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03979j2.cif
_cod_data_source_block           220677lt_auto
_cod_database_code               7132118
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.850
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B)
;
_shelx_res_checksum              15496
_shelx_hkl_checksum              97539
_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 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.905