Palladium-catalyzed three-component reaction of N-tosylhydrazone, norbornene and aryl halide.
Hu, Fangdong; Xia, Ying; Liu, Zhenxing; Ma, Chen; Zhang, Yan; Wang, Jianbo; Organic & biomolecular chemistry 12 (2014) 3590–3593; doi:10.1039/c4ob00590b

data_7153876
_publ_section_title
;
 Palladium-catalyzed three-component reaction of N-tosylhydrazone,
 norbornene and aryl halide.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3590
_journal_page_last               3593
_journal_paper_doi               10.1039/c4ob00590b
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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             2013-04-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.326(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2213(4)
_cell_length_b                   19.9582(12)
_cell_length_c                   13.3944(9)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.6200
_cell_measurement_theta_min      3.6420
_cell_volume                     1660.33(18)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9552
_diffrn_measured_fraction_theta_max 0.7831
_diffrn_measurement_details
;
  1 omega  -57.00   32.00   1.0000    9.1000
omega____ theta____ kappa____ phi______ frames
    -       10.7430  -57.0000  150.0000 89

  2 omega -100.00  -56.00   1.0000    9.1000
omega____ theta____ kappa____ phi______ frames
    -      -11.5243  178.0000 -180.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0032881000
_diffrn_orient_matrix_UB_12      -0.0142878000
_diffrn_orient_matrix_UB_13      -0.0485253000
_diffrn_orient_matrix_UB_21      -0.0409200000
_diffrn_orient_matrix_UB_22      0.0305489000
_diffrn_orient_matrix_UB_23      -0.0204598000
_diffrn_orient_matrix_UB_31      0.1065876000
_diffrn_orient_matrix_UB_32      0.0112575000
_diffrn_orient_matrix_UB_33      -0.0060890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5199
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.05
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86462
_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_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0458P)^2^+0.7305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2580
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00590b2.cif
_cod_data_source_block           exp_1437
_cod_original_cell_volume        1660.32(19)
_cod_database_code               7153876
_chemical_oxdiff_formula         C22H22O2
_reflns_odcompleteness_completeness 95.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H6 of C6, {H1A,H1B} of C1, H18 of C18, H20 of C20, H21 of C21, H3
  of C3, H13 of C13, {H14A,H14B} of C14, H15 of C15, H17 of C17, H8 of C8, H10
  of C10, {H11A,H11B} of C11, {H12A,H12B} of C12
 At 1.5 times of:
  {H22A,H22B,H22C} of C22
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;