A new skeletal rearrangement of 1,7-dimethyl Cookson's cage dione catalyzed by a Lewis acid.
Kotha, Sambasivarao; Cheekatla, Subba Rao; Organic & biomolecular chemistry 18 (2020) 1377–1383; doi:10.1039/c9ob02298h

data_7157318
_publ_section_title
;
 A new skeletal rearrangement of 1,7-dimethyl Cookson's cage dione
 catalyzed by a Lewis acid.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1377
_journal_page_last               1383
_journal_paper_doi               10.1039/c9ob02298h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C14 H18 O3'
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.30
_chemical_melting_point          399.15
_chemical_name_common            'cage ketone'
_chemical_name_systematic
'methyl 4,5a-dimethyl-5-oxooctahydro-1H-1,3-methanocyclobuta[cd]pentalene-6-carboxylate'
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-22
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-04-05 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.235(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5860(4)
_cell_length_b                   17.7133(10)
_cell_length_c                   10.0216(8)
_cell_measurement_reflns_used    2280
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.4990
_cell_measurement_theta_min      2.2810
_cell_volume                     1168.23(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9683
_diffrn_measured_fraction_theta_max 0.9683
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  53.00   0.50    8.00    --  -20.00   0.00 -36.00  326
  2  \w    -60.00 -20.50   0.50    8.00    --  -20.00 -72.00-108.00   79
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0506165000
_diffrn_orient_matrix_UB_12      0.0003221000
_diffrn_orient_matrix_UB_13      0.0611985000
_diffrn_orient_matrix_UB_21      -0.0282291000
_diffrn_orient_matrix_UB_22      -0.0382851000
_diffrn_orient_matrix_UB_23      -0.0099677000
_diffrn_orient_matrix_UB_31      0.0908890000
_diffrn_orient_matrix_UB_32      -0.0117032000
_diffrn_orient_matrix_UB_33      0.0342508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6157
_diffrn_reflns_theta_full        24.9989
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.30
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3320
_exptl_crystal_description       block
_exptl_crystal_F_000             504.2777
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM IN HEXANE'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3441
_refine_diff_density_min         -0.3286
_refine_diff_density_rms         0.0901
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             8.8567
_refine_ls_goodness_of_fit_ref   1.0410
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0410
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.4838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1497
_reflns_number_total             1987
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob02298h2.cif
_cod_data_source_block           SRK-SR-617-S2_Mo
_cod_depositor_comments
'Adding full bibliography for 7157317--7157318.cif.'
_cod_original_cell_volume        1168.22(13)
_cod_database_code               7157318
_reflns_odcompleteness_completeness 83.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.12
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C11(H11), C4(H4), C3(H3), C6(H6), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.534