(3 + 3)-Cyclodimerization of Donor-Acceptor Cyclopropanes. Three Routes to Six-Membered Rings
Olga A. Ivanova; Ekaterina M. Budynina; Alexey O. Chagarovskiy; Igor V. Trushkov; Mikhail Ya. Melnikov; Journal of Organic Chemistry 76 (2011) 8852–8868; doi:10.1021/jo201612w

data_4026709
_publ_contact_author_address
; 
  Department of Chemistry, Moscow State University,
  119992 Moscow, Russian Federation
;
_publ_contact_author_email       rybakov20021@yandex.ru
_publ_contact_author_fax         7--495--9390898
_publ_contact_author_name        'Dr. Victor B. Rybakov'
_publ_contact_author_phone       7--495--9393654
_publ_section_title
;
 (3 + 3)-Cyclodimerization of Donor-Acceptor Cyclopropanes. Three Routes
 to Six-Membered Rings
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8852
_journal_page_last               8868
_journal_paper_doi               10.1021/jo201612w
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H32 O10'
_chemical_formula_sum            'C28 H32 O10'
_chemical_formula_weight         528.54
_chemical_melting_point_gt       446.5
_chemical_melting_point_lt       447.5
_chemical_name_systematic
; 
 Tetramethyl 
 2(SR),5(SR)--bis(4--methoxyphenyl)cyclohexane--1,1,4,4--tetracarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.90(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6656(8)
_cell_length_b                   9.5746(5)
_cell_length_c                   18.6420(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      34.89
_cell_measurement_theta_min      30.22
_cell_volume                     2698.1(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5540
_diffrn_reflns_theta_full        74.98
_diffrn_reflns_theta_max         74.98
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_correction_T_min  0.2877
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
 Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0622P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3797
_reflns_number_total             5540
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201612w_si_003.cif
_cod_data_source_block           tru2448
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026709
_exptl_absorpt_factor_mur        0.165
_diffrn_standards_decay_corr_max 1.019
_diffrn_standards_decay_corr_min 0.990