A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes
Olga A. Ivanova; Ekaterina M. Budynina; Dmitriy A. Skvortsov; Michelle Limoge; Andrei V. Bakin; Alexey O. Chagarovskiy; Igor V. Trushkov; Mikhail Ya. Melnikov; Chem.Commun. 49 (2013) 11482–; doi:10.1039/c3cc44475a

data_7110091
_publ_section_title
;
 A bioinspired route to indanes and cyclopentannulated hetarenes via
 (3+2)-cyclodimerization of donor-acceptor cyclopropanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11482
_journal_paper_doi               10.1039/c3cc44475a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H36 O12'
_chemical_formula_sum            'C30 H36 O12'
_chemical_formula_weight         588.59
_chemical_melting_point_gt       351
_chemical_melting_point_lt       353
_chemical_name_systematic
;
Dimethyl 2-({1RS,2SR,3SR)-3-(3,4-dimethoxyphenyl)-5,6-dimethoxy-2-[2-methoxy-
1-(methoxycarbonyl)-2-oxoethyl]-2,3-dihydro-1H-inden-1-yl}methyl)malonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1750(2)
_cell_length_b                   23.6050(6)
_cell_length_c                   24.7146(6)
_cell_measurement_reflns_used    9402
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      70.69
_cell_measurement_theta_min      3.58
_cell_volume                     5936.0(2)
_computing_cell_refinement       '<i>X--AREA</i> (STOE & CIE, 2012)'
_computing_data_collection       '<i>X--AREA</i> (STOE & CIE, 2012)'
_computing_data_reduction        '<i>X--AREA</i> (STOE & CIE, 2012)'
_computing_molecular_graphics    '<i>Ortep--3</i> (Farrugia, 1997)'
_computing_publication_material  '<i>WinGX</i> (Farrugia, 1999)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
1202 frames, detector distance = 60 mm
;
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.1196
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10447
_diffrn_reflns_theta_full        70.80
_diffrn_reflns_theta_max         70.80
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2496
_exptl_crystal_preparation       'Hexane/diethyl ether = 1/1'
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.668
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     774
_refine_ls_number_reflns         10447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.668
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0021P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0410
_refine_ls_wR_factor_ref         0.0531
_reflns_number_gt                4111
_reflns_number_total             10447
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3cc44475a.txt
_cod_data_source_block           trush33a
_cod_database_code               7110091