Asymmetric Hetero-Diels-Alder Reaction of Diazenes Catalyzed by Chiral Silver Phosphate: Water Participates in the Catalysis and Stereocontrol.
Liu, Bin; Liu, Tong-Yu; Luo, Shi-Wei; Gong, Liu-Zhu; Organic letters 16 (2014) 6164–; doi:10.1021/ol503047s

data_1518296
_publ_section_title
;
 Asymmetric Hetero-Diels-Alder Reaction of Diazenes Catalyzed by Chiral
 Silver Phosphate: Water Participates in the Catalysis and Stereocontrol.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6164
_journal_paper_doi               10.1021/ol503047s
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H38 Cl N3 O4 Si'
_chemical_formula_weight         496.11
_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            4
_cell_length_a                   9.2055(4)
_cell_length_b                   13.5568(5)
_cell_length_c                   23.1410(8)
_cell_measurement_reflns_used    2770
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.4739
_cell_measurement_theta_min      3.2588
_cell_volume                     2887.93(19)
_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-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7282
_diffrn_reflns_theta_full        65.06
_diffrn_reflns_theta_max         65.06
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_T_max  0.6395
_exptl_absorpt_correction_T_min  0.5527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.681
_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   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.1116
_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^)+(0.0529P)^2^+4.4968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.2464
_reflns_number_gt                3240
_reflns_number_total             4495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503047s_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1518296.cif.'
_cod_database_code               1518296