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_7158743
_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         'C14 H16 Br2 O3'
_chemical_formula_sum            'C14 H16 Br2 O3'
_chemical_formula_weight         392.09
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                93.2370(10)
_cell_angle_beta                 108.2430(10)
_cell_angle_gamma                115.398(2)
_cell_formula_units_Z            2
_cell_length_a                   8.81840(10)
_cell_length_b                   8.9121(2)
_cell_length_c                   11.45210(10)
_cell_measurement_reflns_used    5768
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.6320
_cell_measurement_theta_min      4.1830
_cell_volume                     752.85(3)
_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      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_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      6.00  32.00   0.50    0.05    --  -42.80  18.00 -15.00   52
  2  \w      9.00 115.00   0.50    0.05    --   42.80  18.00 -15.00  212
  3  \w    117.00 143.00   0.50    0.05    --   76.50  18.00 -15.00   52
  4  \w     71.00  96.00   0.50    0.05    --   42.80 125.00 150.00   50
  5  \w    100.00 146.00   0.50    0.05    --   76.50 125.00  30.00   92
  6  \w     44.00  88.00   0.50    0.05    --   76.50 -18.00 175.00   88
  7  \w     40.00 115.00   0.50    0.05    --   76.50-125.00  90.00  150
  8  \w     -4.00  22.00   0.50    0.05    --   42.80 -18.00 175.00   52
  9  \w    -28.00  65.00   0.50    0.05    --   42.80 -57.00  30.00  186
 10  \w    -76.00 -33.00   0.50    0.05    --  -42.80  18.00 -15.00   86
 11  \w    -89.00 -64.00   0.50    0.05    --  -42.80 125.00-180.00   50
 12  \w   -128.00 -32.00   0.50    0.05    -- -106.00  57.00 -90.00  192
 13  \w   -102.00 -32.00   0.50    0.05    -- -106.00 125.00 -90.00  140
 14  \w   -113.00 -72.00   0.50    0.05    -- -106.00 125.00  30.00   82
 15  \w   -115.00 -38.00   0.50    0.05    -- -106.00 125.00  60.00  154
 16  \w    -93.00 -29.00   0.50    0.05    -- -106.00  37.00  90.00  128
 17  \w   -107.00 -82.00   0.50    0.05    -- -106.00 125.00 -60.00   50
 18  \w   -129.00 -37.00   0.50    0.05    -- -106.00  77.00 -90.00  184
 19  \w   -113.00 -84.00   0.50    0.05    -- -106.00 -19.00  30.00   58
 20  \w   -128.00 -98.00   0.50    0.05    -- -106.00  37.00  90.00   60
 21  \w   -125.00 -64.00   0.50    0.05    -- -106.00  57.00  90.00  122
 22  \w   -120.00 -53.00   0.50    0.05    --  -42.80 -18.00 175.00  134
 23  \w   -130.00 -27.00   0.50    0.05    -- -106.00  18.00 -15.00  206
 24  \w   -110.00 -84.00   0.50    0.05    -- -106.00 125.00-180.00   52
 25  \w   -123.00 -28.00   0.50    0.05    -- -106.00  37.00-180.00  190
 26  \w   -173.00-124.00   0.50    0.05    -- -106.00 -19.00  30.00   98
 27  \w   -177.00 -91.00   0.50    0.05    -- -106.00 -37.00 120.00  172
 28  \w   -176.00-116.00   0.50    0.05    -- -106.00 -18.00 175.00  120
;
_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      -0.0290928000
_diffrn_orient_matrix_UB_12      0.1583645000
_diffrn_orient_matrix_UB_13      0.0061092000
_diffrn_orient_matrix_UB_21      -0.1668062000
_diffrn_orient_matrix_UB_22      -0.0981618000
_diffrn_orient_matrix_UB_23      0.0339741000
_diffrn_orient_matrix_UB_31      0.1216916000
_diffrn_orient_matrix_UB_32      0.0616973000
_diffrn_orient_matrix_UB_33      0.1411163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.985
_diffrn_reflns_theta_min         4.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78131
_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    1.730
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.795
_refine_diff_density_min         -1.559
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0438P)^2^+0.9259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2852
_reflns_number_total             2963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01096h2.cif
_cod_data_source_block           dibromo
_cod_original_cell_volume        752.85(2)
_cod_database_code               7158743
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H16 Br2 O3'
_chemical_oxdiff_usercomment     hexane/ether
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C4(H4), C9(H9)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C00I(H00A,H00B,H00C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              40109
_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 2.432
_oxdiff_exptl_absorpt_empirical_full_min 0.648