Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl groups with carbon–carbon double bonds
Lokshin, Vladimir; Clavier, Hervé; Khodorkovsky, Vladimir; New Journal of Chemistry 44 (2020) 14373–14378; doi:10.1039/D0NJ02923H

data_7059848
_publ_section_title
;
 Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl
 groups with carbon--carbon double bonds
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14373
_journal_page_last               14378
_journal_paper_doi               10.1039/D0NJ02923H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C27 H20 O4'
_chemical_formula_sum            'C27 H20 O4'
_chemical_formula_weight         408.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-28
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;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7159(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5128(2)
_cell_length_b                   5.73808(8)
_cell_length_c                   26.7156(5)
_cell_measurement_reflns_used    13947
_cell_measurement_temperature    293
_cell_measurement_theta_max      65.1530
_cell_measurement_theta_min      5.4630
_cell_volume                     2028.31(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            AtlasS2
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_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -110.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -77.0000 -120.0000 118

  2 omega  -27.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000  150.0000 80

  3 omega  -49.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000    0.0000 103

  4 omega -122.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -57.0000   30.0000 128

  5 omega   58.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  178.0000  -60.0000 73

  6 omega   35.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  -99.0000  -30.0000 47

  7 omega    5.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   90.0000  168.9528 25

  8 omega    6.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   87.0000   39.4436 28

  9 omega   11.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   84.0000  110.7460 25

 10 omega   16.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   81.0000  -96.6131 25

 11 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000   74.9993 26

 12 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  121.7358 26

 13 omega   20.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000   36.3694 25

 14 omega   20.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  -12.8973 27

 15 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  174.6470 26

 16 omega   20.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  -67.2709 25

 17 omega   97.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -144.1121 65

 18 omega   25.00   56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -144.1121 31

 19 omega   29.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -65.5087 69

 20 omega   94.00  156.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000   41.5478 62

 21 omega   34.00   61.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000   41.5478 27

 22 omega  139.00  166.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   57.0000  153.8766 27

 23 omega   39.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   57.0000  153.8766 46

 24 omega   61.00  150.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  178.0000  120.0000 89

 25 omega   56.00  130.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -180.0000 74

 26 omega   37.00  107.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  120.0000 70

 27 omega   56.00  144.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -30.0000 88

 28 omega   56.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   30.0000 106

 29 omega   56.00  158.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -120.0000 102

 30 omega   24.00  115.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 91

 31 omega   28.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000   90.0000 76

 32 omega   56.00  163.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   60.0000 107

 33 omega   16.00  126.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 110

 34 omega   56.00  172.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -150.0000 116

 35 omega   56.00  135.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000    0.0000 79

 36 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -90.0000 122

 37 omega   56.00  156.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   90.0000 100

 38 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  120.0000 122

 39 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -60.0000 122

 40 omega   56.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  150.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0898771000
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_diffrn_orient_matrix_UB_21      -0.0637361000
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.946
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_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_theta_max         65.316
_diffrn_reflns_theta_min         4.039
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.337
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_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.126
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_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0494P)^2^+0.4332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                3210
_reflns_number_total             3465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02923h2.cif
_cod_data_source_block           cyclo5ch
_cod_depositor_comments
;Adding full bibliography for 7059847--7059851.cif.

 Adding full bibliography for 7059847--7059851.cif.
;
_cod_database_code               7059848
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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:
 C1(H1), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'