Synthesis of 1,4-Cyclohexadiene-Based Acetylenic Macrocycles with Cadiot-Chodkiewicz Coupling. Structure of a Tub-Shaped Tetrameric Container
Arkasish Bandyopadhyay; Babu Varghese; Sethuraman Sankararaman; Journal of Organic Chemistry 71 (2006) 4544–4548; doi:10.1021/jo0605290

data_4021748
_publ_section_title
;
 Synthesis of 1,4-Cyclohexadiene-Based Acetylenic Macrocycles
 with Cadiot-Chodkiewicz Coupling.
 Structure of a Tub-Shaped Tetrameric Container
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4544
_journal_page_last               4548
_journal_paper_doi               10.1021/jo0605290
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C39 H33 O6'
_chemical_formula_weight         597.65
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.000(10)
_cell_angle_beta                 111.751(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            8
_cell_length_a                   14.6298(10)
_cell_length_b                   25.9566(10)
_cell_length_c                   18.5998(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     6560.2(6)
_computing_cell_refinement       'cad4 system programs'
_computing_data_collection       'cad4 system programs'
_computing_data_reduction        'XCAD4 (WINGX)'
_computing_molecular_graphics    'ORTEP32 (WINGX)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (WINGX)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'cad4 diffractometer'
_diffrn_measurement_method       'omega twotheta'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5971
_diffrn_reflns_theta_full        67.97
_diffrn_reflns_theta_max         67.97
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '1 hour'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.286
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.1926
_refine_ls_R_factor_gt           0.1085
_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^)+(0.1658P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.2680
_reflns_number_gt                2196
_reflns_number_total             5971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0605290si20060310_053412.cif
_cod_depositor_comments
;

2020-12-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C78 H66 O12'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1195.31
_cod_database_code               4021748