Asymmetric Annulation of 3-Alkynylacrylaldehydes with Styrene-Type Olefins by Synergetic Relay Catalysis from AgOAc and Chiral Phosphoric Acid.
Zhang, Hao; Zhu, Le; Wang, Shaozhong; Yao, Zhu-Jun; The Journal of organic chemistry 79 (2014) 7063–7074; doi:10.1021/jo501196n

data_4029811
_publ_section_title
;
 Asymmetric Annulation of 3-Alkynylacrylaldehydes with Styrene-Type
 Olefins by Synergetic Relay Catalysis from AgOAc and Chiral Phosphoric
 Acid.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7063
_journal_page_last               7074
_journal_paper_doi               10.1021/jo501196n
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration .ad
_chemical_formula_sum            'C24 H20 Br N O2'
_chemical_formula_weight         434.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7032(12)
_cell_length_b                   14.9947(17)
_cell_length_c                   25.551(3)
_cell_measurement_reflns_used    4891
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.54
_cell_measurement_theta_min      2.34
_cell_volume                     4100.7(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27835
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  0.6877
_exptl_absorpt_correction_T_min  0.5819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         9387
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                4915
_reflns_number_total             9387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501196n_si_002.cif
_cod_data_source_block           wpp1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029810--4029811.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4029811