Rapid Sonogashira cross-coupling of iodoferrocenes and the unexpected cyclo-oligomerization of 4-ethynylphenylthioacetate
Michael S. Inkpen; Andrew J. P. White; Tim Albrecht; Nicholas J. Long; Chem.Commun. 49 (2013) 5663–; doi:10.1039/c3cc43116a

data_7109392
_publ_section_title
;
 Rapid Sonogashira cross-coupling of iodoferrocenes and the unexpected
 cyclo-oligomerization of 4-ethynylphenylthioacetate
;
_journal_name_full               Chem.Commun.
_journal_page_first              5663
_journal_paper_doi               10.1039/c3cc43116a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C30 H24 O3 S3, C H2 Cl2'
_chemical_formula_sum            'C31 H26 Cl2 O3 S3'
_chemical_formula_weight         613.60
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5311(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   24.8640(4)
_cell_length_b                   24.0808(3)
_cell_length_c                   15.1854(3)
_cell_measurement_reflns_used    18096
_cell_measurement_temperature    173
_cell_measurement_theta_max      32.6427
_cell_measurement_theta_min      3.0265
_cell_volume                     9033.2(3)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 15.9825
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            51253
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         32.72
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             3816
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 6835 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1099
_refine_ls_number_reflns         22101
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0872P)^2^+0.7278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                18011
_reflns_number_total             22101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43116a.txt
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7109392