Reductive Coupling of Allenoates with Aldehydes Catalyzed by Halogenotin Hydride
Suzuki, Itaru; Hamada, Yuya; Uji, Yuki; Shibata, Ikuya; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01096H

data_7158744
_publ_section_title
;
 Reductive Coupling of Allenoates with Aldehydes Catalyzed by Halogenotin
 Hydride
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01096H
_journal_year                    2022
_chemical_formula_moiety         'C13 H11 Cl O4'
_chemical_formula_sum            'C13 H11 Cl O4'
_chemical_formula_weight         266.67
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                84.271(4)
_cell_angle_beta                 88.200(5)
_cell_angle_gamma                75.258(5)
_cell_formula_units_Z            4
_cell_length_a                   6.3452(4)
_cell_length_b                   10.1024(6)
_cell_length_c                   19.4282(10)
_cell_measurement_reflns_used    5343
_cell_measurement_temperature    173
_cell_measurement_theta_max      73.8210
_cell_measurement_theta_min      4.5450
_cell_volume                     1198.35(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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    -29.00  64.00   0.50    2.00    --   42.80 -57.00  90.00  186
  2  \w     32.00  57.00   0.50    5.00    --   76.50 -98.00  78.00   50
  3  \w     18.00  80.00   0.50    2.00    --   42.80 -98.00  78.00  124
  4  \w    -29.00  14.00   0.50    2.00    --   42.80 -98.00  78.00   86
  5  \w   -114.00 -73.00   0.50    2.00    --  -42.80-125.00-120.00   82
  6  \w   -140.00 -74.00   0.50    5.00    -- -106.00-125.00 -30.00  132
  7  \w   -111.00 -85.00   0.50    5.00    -- -106.00 -37.00 -30.00   52
  8  \w   -135.00 -81.00   0.50    5.00    -- -106.00 -19.00  30.00  108
  9  \w    -96.00 -60.00   0.50    5.00    -- -106.00  57.00  30.00   72
 10  \w   -116.00 -32.00   0.50    5.00    -- -106.00 125.00 -60.00  168
 11  \w    -75.00 -41.00   0.50    5.00    -- -106.00 125.00  30.00   68
 12  \w    -65.00 -39.00   0.50    5.00    -- -106.00  57.00 120.00   52
 13  \w   -116.00 -83.00   0.50    5.00    -- -106.00 125.00  30.00   66
 14  \w   -108.00 -66.00   0.50    5.00    -- -106.00 125.00 -30.00   84
 15  \w   -114.00 -39.00   0.50    5.00    -- -106.00  77.00 -90.00  150
 16  \w    -61.00  30.00   0.50    2.00    --  -42.80  98.00-174.00  182
 17  \w     74.00 109.00   0.50    2.00    --   42.80 125.00 -30.00   70
 18  \w     77.00 150.00   0.50    5.00    --   76.50 125.00  30.00  146
 19  \w     74.00 116.00   0.50    2.00    --   42.80 125.00 120.00   84
 20  \w     92.00 117.00   0.50    5.00    --   76.50  98.00-174.00   50
 21  \w   -106.00 -76.00   0.50    5.00    -- -106.00  98.00-174.00   60
 22  \w   -112.00 -33.00   0.50    5.00    -- -106.00 125.00-120.00  158
 23  \w   -126.00 -32.00   0.50    5.00    -- -106.00  57.00 -90.00  188
 24  \w   -119.00 -68.00   0.50    5.00    -- -106.00  57.00 120.00  102
 25  \w   -167.00-141.00   0.50    5.00    -- -106.00 -19.00  30.00   52
 26  \w   -176.00-147.00   0.50    5.00    -- -106.00 -37.00 -30.00   58
 27  \w   -177.00-117.00   0.50    5.00    -- -106.00 -99.00   0.00  120
 28  \w   -151.00-109.00   0.50    5.00    -- -106.00 -98.00  78.00   84
 29  \w   -171.00-146.00   0.50    5.00    -- -106.00-125.00 -30.00   50
 30  \w   -172.00-100.00   0.50    5.00    -- -106.00 -57.00-120.00  144
 31  \w   -131.00 -84.00   0.50    5.00    -- -106.00 -99.00-180.00   94
 32  \w   -177.00-139.00   0.50    5.00    -- -106.00 -99.00-180.00   76
 33  \w   -177.00 -83.00   0.50    5.00    -- -106.00 -37.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0627519000
_diffrn_orient_matrix_UB_12      -0.1315823000
_diffrn_orient_matrix_UB_13      0.0502103000
_diffrn_orient_matrix_UB_21      0.1494973000
_diffrn_orient_matrix_UB_22      -0.0738321000
_diffrn_orient_matrix_UB_23      -0.0559177000
_diffrn_orient_matrix_UB_31      0.1916892000
_diffrn_orient_matrix_UB_32      0.0482271000
_diffrn_orient_matrix_UB_33      0.0265216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.523
_diffrn_reflns_theta_min         4.546
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.068
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.581
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.1282
_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^)+(0.1605P)^2^+16.1122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3923
_refine_ls_wR_factor_ref         0.3947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4160
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01096h2.cif
_cod_data_source_block           spiro2
_cod_database_code               7158744
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H15 O Cl'
_chemical_oxdiff_usercomment     THF/DCM/Hexane
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C20(H20), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C18(H18A,H18B), C17(H17A,H17B), C4(H4A,H4B), C3(H3A,H3B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C22(H22), C13(H13), C10(H10), C9(H9), C11(H11), C23(H23)
;
_shelx_res_checksum              40470
_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 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.556