Donor-acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes.
Ivanov, Konstantin L.; Bezzubov, Stanislav I.; Melnikov, Mikhail Ya; Budynina, Ekaterina M.; Organic & biomolecular chemistry 16 (2018) 3897–3909; doi:10.1039/c8ob00377g

data_7156153
_publ_section_title
;
 Donor-acceptor cyclopropanes as ortho-quinone methide equivalents in
 formal (4 + 2)-cycloaddition to alkenes.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3897
_journal_page_last               3909
_journal_paper_doi               10.1039/c8ob00377g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C13 H13 Cl O5'
_chemical_formula_sum            'C13 H13 Cl O5'
_chemical_formula_weight         284.68
_chemical_melting_point_gt       373
_chemical_melting_point_lt       374
_chemical_name_systematic
;
Dimethyl 2-(5-chloro-2-hydroxyphenyl)cyclopropane-1,1-dicarboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.50(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.594(2)
_cell_length_b                   8.102(2)
_cell_length_c                   17.944(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      13
_cell_volume                     1350.4(6)
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_collection       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.972
_diffrn_reflns_theta_min         2.193
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_transmission_factor_max   0.904
_exptl_transmission_factor_min   0.350
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.2223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1696
_reflns_number_total             2642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00377g2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 7156149--7156154.cif.'
_cod_original_cell_volume        1350.3(6)
_cod_database_code               7156153
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.904
_shelx_res_checksum              46987