Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
Ping-Xin Zhou; Jian-Yi Luo; Lian-Biao Zhao; Yu-Ying Ye; Yong-Min Liang; Chem.Commun. 49 (2013) 3254–; doi:10.1039/c3cc40577j

data_7109063
_publ_section_title
;
 Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of
 isoindolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              3254
_journal_paper_doi               10.1039/c3cc40577j
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 Cl N'
_chemical_formula_sum            'C24 H22 Cl N'
_chemical_formula_weight         359.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-04
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.784(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.0639(18)
_cell_length_b                   6.1724(3)
_cell_length_c                   21.5055(16)
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    290.3(2)
_cell_measurement_theta_max      28.4588
_cell_measurement_theta_min      2.9758
_cell_volume                     3858.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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      290.3(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.9723
_diffrn_measurement_details
;
1 omega -7.00 23.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -19.1930 -99.0000 -60.0000 30
2 omega 5.00 89.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -180.0000 84
3 omega 31.00 56.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -77.0000 -30.0000 25
4 omega -42.00 58.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -19.0000 -180.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0242705000
_diffrn_orient_matrix_UB_12      0.0110919000
_diffrn_orient_matrix_UB_13      -0.0094553000
_diffrn_orient_matrix_UB_21      -0.0011374000
_diffrn_orient_matrix_UB_22      -0.0282957000
_diffrn_orient_matrix_UB_23      0.0315297000
_diffrn_orient_matrix_UB_31      0.0021386000
_diffrn_orient_matrix_UB_32      0.1108283000
_diffrn_orient_matrix_UB_33      0.0089777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8511
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0266P)^2^+1.9809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                4460
_reflns_number_total             6911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40577j.txt
_cod_data_source_block           zhoupx0104_2
_cod_depositor_comments
;

2017-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H22 Cl N)'
_cod_original_formula_sum        'C48 H44 Cl2 N2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     719.75
_cod_database_code               7109063
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H13 of C13, H10 of C10, H14 of C14, H1 of C1, H3 of C3, H4 of C4, H5 of C5,
H6 of C6, {H8A,H8B} of C8, H28 of C28, H30 of C30, H27 of C27, H29 of C29,
H24 of C24, H25 of C25, H23 of C23, {H32A,H32B} of C32, H35 of C35, H34 of
C34, H17 of C17, H18 of C18, H20 of C20, H21 of C21, H48 of C48, H47 of C47,
H45 of C45, H44 of C44, H42 of C42, H41 of C41, H38 of C38
At 1.5 times of:
{H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H40A,H40B,H40C} of C40,
{H39A,H39B,H39C} of C39
2.a Ternary CH refined with riding coordinates:
C1(H1), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14), C17(H17),
C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
C30(H30), C34(H34), C35(H35), C38(H38), C41(H41), C42(H42), C44(H44),
C45(H45), C47(H47), C48(H48)
2.d Idealised Me refined as rotating group:
C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C39(H39A,H39B,H39C), C40(H40A,H40B,
H40C)
;