Copper-Catalyzed Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with Glyoxals.
Li, Yanan; Hu, Yanbin; Zhang, Sheng; Sun, Jianan; Li, Lijun; Zha, Zhenggen; Wang, Zhiyong; The Journal of organic chemistry 81 (2016) 2993–2999; doi:10.1021/acs.joc.5b02780

data_4031954
_publ_section_title
;
 Copper-Catalyzed Enantioselective Hetero-Diels-Alder Reaction of
 Danishefsky's Diene with Glyoxals.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2993
_journal_page_last               2999
_journal_paper_doi               10.1021/acs.joc.5b02780
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H9 Br O3'
_chemical_formula_weight         281.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.708(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3040(3)
_cell_length_b                   6.0907(3)
_cell_length_c                   16.9947(10)
_cell_measurement_reflns_used    1328
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.0880
_cell_measurement_theta_min      5.2000
_cell_volume                     548.77(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1854
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.220
_diffrn_reflns_theta_min         5.208
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details
;
 Flack x determined using 266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0661
_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^)+(0.0851P)^2^+2.0456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.268
_reflns_Friedel_fraction_full    0.324
_reflns_Friedel_fraction_max     0.315
_reflns_number_gt                1325
_reflns_number_total             1377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02780_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4031954
_shelx_estimated_absorpt_t_min   0.296
_shelx_estimated_absorpt_t_max   0.333
_shelxl_version_number           2013-4
_shelx_res_checksum              37019
_shelx_hkl_checksum              32945