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_7132120
_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 H16 Cl N O3'
_chemical_formula_sum            'C20 H16 Cl N O3'
_chemical_formula_weight         353.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.733(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0167(3)
_cell_length_b                   11.7335(4)
_cell_length_c                   8.0325(2)
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.3660
_cell_measurement_theta_min      3.7360
_cell_volume                     821.88(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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   -119.00 -40.00   0.50    0.05    --  -75.32 -15.00-120.00  158
  2  \w    -50.00 -18.00   0.50    0.05    --  -59.24 119.00 -10.00   64
  3  \w    -88.00 -56.00   0.50    0.05    --  -71.82 119.00 -10.00   64
  4  \w    -89.00 -63.00   0.50    0.05    --  -75.32 119.00 -10.00   52
  5  \w     41.00 102.00   0.50    0.05    --   56.05  15.00 -30.00  122
  6  \w     50.00 133.00   0.50    0.05    --   83.87  15.00  30.00  166
  7  \w     60.00 124.00   0.50    0.05    --   75.94  15.00-120.00  128
  8  \w     71.00  97.00   0.50    0.05    --   83.87  15.00-180.00   52
  9  \w     18.00  47.00   0.50    0.05    --   56.05-119.00 -95.00   58
 10  \w     52.00  77.00   0.50    0.05    --   56.05-119.00 -95.00   50
 11  \w     33.00  58.00   0.50    0.05    --   69.01-119.00 -95.00   50
 12  \w     39.00  64.00   0.50    0.05    --   75.94-119.00 -95.00   50
 13  \w     64.00  97.00   0.50    0.05    --   83.87-119.00 -95.00   66
 14  \w     48.00  91.00   0.50    0.05    --   83.87 -95.00 -60.00   86
 15  \w     32.00  91.00   0.50    0.05    --   75.94-111.00 -60.00  118
 16  \w     67.00  92.00   0.50    0.05    --   83.87 -95.00   0.00   50
 17  \w     32.00  64.00   0.50    0.05    --   75.94-111.00  90.00   64
 18  \w     33.00  66.00   0.50    0.05    --   75.94 -95.00  90.00   66
 19  \w     35.00  74.00   0.50    0.05    --   69.01 -95.00   0.00   78
 20  \w     43.00  90.00   0.50    0.05    --   83.87 -95.00 -30.00   94
 21  \w     67.00  92.00   0.50    0.05    --   83.87 -95.00 -90.00   50
 22  \w     41.00  66.00   0.50    0.05    --   83.87 -95.00-180.00   50
;
_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      0.1415203000
_diffrn_orient_matrix_UB_12      0.0783692000
_diffrn_orient_matrix_UB_13      0.0325789000
_diffrn_orient_matrix_UB_21      0.1052748000
_diffrn_orient_matrix_UB_22      -0.1040703000
_diffrn_orient_matrix_UB_23      0.0553224000
_diffrn_orient_matrix_UB_31      0.0082787000
_diffrn_orient_matrix_UB_32      -0.0170652000
_diffrn_orient_matrix_UB_33      -0.1875517000
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5108
_diffrn_reflns_point_group_measured_fraction_full 0.694
_diffrn_reflns_point_group_measured_fraction_max 0.694
_diffrn_reflns_theta_full        66.563
_diffrn_reflns_theta_max         66.563
_diffrn_reflns_theta_min         3.767
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.430
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2012
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0736P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.389
_reflns_Friedel_fraction_full    0.390
_reflns_Friedel_fraction_max     0.390
_reflns_number_gt                1939
_reflns_number_total             2012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03979j2.cif
_cod_data_source_block           230734lt_auto
_cod_original_cell_volume        821.88(4)
_cod_database_code               7132120
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.776
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.97(3)
 0.03(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
3.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
;
_shelx_res_checksum              26145
_shelx_hkl_checksum              34361
_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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.747