Synthesis of polycyclic substituted vinylarenes via a one-pot intramolecular aryl alkylation-N-tosylhydrazone insertion reaction
Xin-Xing Wu; Ping-Xin Zhou; Li-Jing Wang; Peng-Fei Xu; Yong-Min Liang; Chem.Commun. 50 (2014) 3882–; doi:10.1039/C4CC00809J

data_7112176
_publ_section_title
;
 Synthesis of polycyclic substituted vinylarenes via a one-pot
 intramolecular aryl alkylation-N-tosylhydrazone insertion reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3882
_journal_paper_doi               10.1039/C4CC00809J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C24 H23 N O2 S'
_chemical_formula_sum            'C24 H23 N O2 S'
_chemical_formula_weight         389.49
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-11-27
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
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_cell_angle_alpha                90
_cell_angle_beta                 96.402(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9663(6)
_cell_length_b                   8.2591(4)
_cell_length_c                   20.6407(10)
_cell_measurement_reflns_used    1893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2460
_cell_measurement_theta_min      3.4900
_cell_volume                     2027.22(17)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0475906000
_diffrn_orient_matrix_UB_12      -0.0281559000
_diffrn_orient_matrix_UB_13      0.0204580000
_diffrn_orient_matrix_UB_21      -0.0344668000
_diffrn_orient_matrix_UB_22      -0.0154972000
_diffrn_orient_matrix_UB_23      0.0250978000
_diffrn_orient_matrix_UB_31      -0.0101006000
_diffrn_orient_matrix_UB_32      -0.0796846000
_diffrn_orient_matrix_UB_33      -0.0121374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8380
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.003
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0050(8)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.1923P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00809j2.cif
_cod_data_source_block           wuxy1126
_cod_original_cell_volume        2027.24(17)
_cod_database_code               7112176
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.78
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              13949
_shelx_hkl_checksum              95006