Regioselective Intermolecular [2 + 2]-Cycloaddition of α-Iodo-Unsaturated Ketones Promoted by Diisobutylaluminum Hydride.
Zhu, Hai-Tao; Ke, Sen; Zhou, Ni-Ni; Fan, Ming-Jin; Yang, De-Suo; Organic letters 18 (2016) 4554–4557; doi:10.1021/acs.orglett.6b02195

data_1543991
_publ_section_title
;
 Regioselective Intermolecular [2 + 2]-Cycloaddition of
 \a-Iodo-Unsaturated Ketones Promoted by Diisobutylaluminum Hydride.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4554
_journal_page_last               4557
_journal_paper_doi               10.1021/acs.orglett.6b02195
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C44 H28 O4'
_chemical_formula_sum            'C44 H28 O4'
_chemical_formula_weight         620.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-31
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9399(4)
_cell_length_b                   20.8101(7)
_cell_length_c                   19.6719(6)
_cell_measurement_reflns_used    1615
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      28.7950
_cell_measurement_theta_min      3.8880
_cell_volume                     3250.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000   90.0000 26

  2 omega  -41.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -77.0000  150.0000 91

  3 omega   41.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000   30.0000 42
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0186552000
_diffrn_orient_matrix_UB_12      0.0326658000
_diffrn_orient_matrix_UB_13      0.0069951000
_diffrn_orient_matrix_UB_21      0.0650310000
_diffrn_orient_matrix_UB_22      -0.0006712000
_diffrn_orient_matrix_UB_23      -0.0247132000
_diffrn_orient_matrix_UB_31      -0.0583415000
_diffrn_orient_matrix_UB_32      0.0096960000
_diffrn_orient_matrix_UB_33      -0.0253105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8841
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+1.1382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2220
_reflns_number_total             3199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02195_si_002.cif
_cod_data_source_block           wangjia1230
_cod_depositor_comments          'Adding full bibliography for 1543991.cif.'
_cod_database_code               1543991
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_date_sample_data_collection 2014-12-31
_olex2_submission_special_instructions 'No special instructions were received'