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_7109920
_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_formula_moiety         'C21 H19 Cl O4'
_chemical_formula_sum            'C21 H19 Cl O4'
_chemical_formula_weight         370.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.226(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9515(5)
_cell_length_b                   21.4155(17)
_cell_length_c                   22.7131(18)
_cell_measurement_reflns_used    1883
_cell_measurement_temperature    296.01(12)
_cell_measurement_theta_max      20.7230
_cell_measurement_theta_min      3.3810
_cell_volume                     3827.9(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      296.01(12)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.8949
_diffrn_measurement_details
;
  1 omega  -80.00  -30.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -38.0000 -150.0000 50

  2 omega  -20.00   22.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000  -60.0000 42

  3 omega  -99.00  -59.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000   60.0000 40

  4 omega  -48.00   46.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  -30.0000 94

  5 omega   79.00  104.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  -60.0000 25

  6 omega   37.00   69.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  -60.0000 32

  7 omega   -3.00   23.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  120.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0303063000
_diffrn_orient_matrix_UB_12      0.0250503000
_diffrn_orient_matrix_UB_13      -0.0159820000
_diffrn_orient_matrix_UB_21      0.0296396000
_diffrn_orient_matrix_UB_22      -0.0215953000
_diffrn_orient_matrix_UB_23      -0.0198568000
_diffrn_orient_matrix_UB_31      -0.0795574000
_diffrn_orient_matrix_UB_32      0.0015061000
_diffrn_orient_matrix_UB_33      -0.0186116000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18892
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0017(3)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         7518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1858
_refine_ls_R_factor_gt           0.0731
_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^)+(0.0445P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                2959
_reflns_number_total             7518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45583a.txt
_cod_data_source_block           yeyy0523
_cod_database_code               7109920
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32),
  C34(H34), C35(H35), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C39(H39A,H39B,H39C), C41(H41A,H41B,
 H41C)
;