(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_4026708
_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_formula_moiety         'C32 H40 O14, 0.25(C H CL3), 0.5(H2 O)'
_chemical_formula_sum            'C32.25 H41.25 Cl0.75 O14.5'
_chemical_formula_weight         686.48
_chemical_melting_point          487.2(4)
_chemical_name_systematic
;
 Tetramethyl 2,2'-((9S,10R)-1,2,3,5,6,7-
hexamethoxy-9,10-dihydroanthracene-
9,10-diyl)-bis(methylene)dimalonate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                82.36(2)
_cell_angle_beta                 80.27(2)
_cell_angle_gamma                77.15(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2762(8)
_cell_length_b                   9.5852(9)
_cell_length_c                   12.5970(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      33.92
_cell_measurement_theta_min      30.01
_cell_volume                     955.53(19)
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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    0.0230
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3821
_diffrn_reflns_theta_full        74.87
_diffrn_reflns_theta_max         74.87
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        7
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    4.667
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       Prism
_exptl_crystal_F_000             446
_exptl_crystal_preparation       CDCl~3~
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.0025(18)
_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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0350
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3062
_reflns_number_total             3821
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201612w_si_002.cif
_cod_data_source_block           cpd2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'x--ray' changed to 'x-ray' according
to the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C32.25 H41.25 Cl0.75 O14.50'
_cod_database_code               4026708
_diffrn_standards_decay_corr_max 1.072
_diffrn_standards_decay_corr_min 1.000