Palladium-catalyzed insertion of alpha,beta-unsaturated N-tosylhydrazones and trapping with carbon nucleophiles
Yu-Ying Ye; Ping-Xin Zhou; Jian-Yi Luo; Mei-Jin Zhong; Yong-Min Liang; Chem.Commun. 49 (2013) 10190–; doi:10.1039/c3cc45583a

data_7109919
_publ_section_title
;
 Palladium-catalyzed insertion of alpha,beta-unsaturated N-tosylhydrazones
 and trapping with carbon nucleophiles
;
_journal_name_full               Chem.Commun.
_journal_page_first              10190
_journal_paper_doi               10.1039/c3cc45583a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.6554(13)
_cell_length_b                   15.1602(9)
_cell_length_c                   8.7821(10)
_cell_measurement_reflns_used    3117
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0470
_cell_measurement_theta_min      3.7730
_cell_volume                     4081.4(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9864
_diffrn_measured_fraction_theta_max 0.8253
_diffrn_measurement_details
;
  1 omega   35.00   61.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000   90.0000 22

  2 omega   -4.00   50.00   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -19.0000 -180.0000 45

  3 omega  -18.00   67.20   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -99.0000  -60.0000 71

  4 omega  -96.00  -55.20   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  178.0000   30.0000 34

  5 omega  -46.00   18.80   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000  150.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0051635000
_diffrn_orient_matrix_UB_12      0.0014512500
_diffrn_orient_matrix_UB_13      -0.0786625500
_diffrn_orient_matrix_UB_21      0.0225347000
_diffrn_orient_matrix_UB_22      -0.0023326500
_diffrn_orient_matrix_UB_23      0.0178857500
_diffrn_orient_matrix_UB_31      -0.0009685000
_diffrn_orient_matrix_UB_32      -0.0467171000
_diffrn_orient_matrix_UB_33      -0.0033407000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9147
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0603
_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^)+(0.1169P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                3181
_reflns_number_total             3919
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45583a.txt
_cod_data_source_block           liangym0318
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7109919
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H14 of C14, {H2A,H2B,H2C} of C2, H3 of C3, H4 of C4, H5 of C5, H8 of C8,
  H16 of C16, H17 of C17, H18 of C18, H19 of C19, H10 of C10, H11 of C11
 At 1.5 times of:
  {H1BA,H1BB,H1BC} of C1B, {H1AA,H1AB,H1AC} of C1A
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C4(H4), C5(H5), C8(H8), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;