A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives.
Raveendra Babu, Kaki; Khan, Faiz Ahmed; Organic & biomolecular chemistry 13 (2015) 299–308; doi:10.1039/c4ob01977f

data_7154165
_publ_section_title
;
 A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl
 alcohols leading to indenones and a de novo synthesis of ninhydrin
 derivatives.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              299
_journal_page_last               308
_journal_paper_doi               10.1039/c4ob01977f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C20 H12 Cl4 O2'
_chemical_formula_sum            'C20 H12 Cl4 O2'
_chemical_formula_weight         426.10
_chemical_name_systematic        '2,3-Dichloro-5-methyl-1H-inden-1-one '
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
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_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   8.8145(3)
_cell_length_c                   14.806(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1820.3(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.980
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.994
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_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3396
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.518
_diffrn_reflns_theta_min         5.874
_exptl_absorpt_coefficient_mu    6.015
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0764P)^2^+0.8646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1359
_reflns_number_total             1717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01977f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7154165.cif.'
_cod_database_code               7154165
_shelxl_version_number           2013-4
_shelx_res_checksum              64219