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_7059850
_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         '2(C28 H22 O4)'
_chemical_formula_sum            'C56 H44 O8'
_chemical_formula_weight         844.91
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-25
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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                 96.220(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7429(9)
_cell_length_b                   19.0061(5)
_cell_length_c                   11.4935(2)
_cell_measurement_reflns_used    4458
_cell_measurement_temperature    293
_cell_measurement_theta_max      63.4650
_cell_measurement_theta_min      4.4900
_cell_volume                     4504.5(2)
_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
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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_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_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega -133.00  -69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201 -166.0000 -124.0000 64

  2 omega -115.00  -80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -99.0000 -180.0000 35

  3 omega  -41.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000 -180.0000 87

  4 omega -120.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -38.0000   30.0000 128

  5 omega -119.00  -80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -99.0000  120.0000 39

  6 omega   -4.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201   57.0000  -30.0000 28

  7 omega   76.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201   57.0000  -30.0000 26

  8 omega    2.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  -99.0000  -60.0000 45

  9 omega   58.00  129.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  178.0000  -60.0000 71

 10 omega   16.00   55.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 39

 11 omega   24.00   52.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   60.0000 28

 12 omega   55.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  -30.0000 54

 13 omega  146.00  173.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000 -180.0000 27

 14 omega   50.00  112.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000  120.0000 62

 15 omega   71.00  121.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  178.0000    0.0000 50

 16 omega   17.00   42.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 25

 17 omega   11.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   90.0000 78

 18 omega   20.00   62.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   30.0000 42

 19 omega   59.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 56

 20 omega  102.00  130.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000 -180.0000 28

 21 omega   69.00  137.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 68

 22 omega  145.00  174.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000  120.0000 29

 23 omega   21.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -45.0000  -30.0000 70

 24 omega   28.00  124.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000   90.0000 96

 25 omega    4.00   36.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  -30.0000 32

 26 omega    3.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   15.0000   60.0000 175
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0307613000
_diffrn_orient_matrix_UB_12      0.0705010000
_diffrn_orient_matrix_UB_13      -0.0424324000
_diffrn_orient_matrix_UB_21      -0.0671793000
_diffrn_orient_matrix_UB_22      -0.0274967000
_diffrn_orient_matrix_UB_23      0.0240223000
_diffrn_orient_matrix_UB_31      0.0111303000
_diffrn_orient_matrix_UB_32      0.0290567000
_diffrn_orient_matrix_UB_33      0.1256745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26870
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.286
_diffrn_reflns_theta_min         4.288
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73770
_exptl_absorpt_correction_type   multi-scan
_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    1.246
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_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         7659
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0798P)^2^+2.1018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4941
_reflns_number_total             7659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02923h2.cif
_cod_data_source_block           photo5cch3
_cod_depositor_comments
;Adding full bibliography for 7059847--7059851.cif.

 Adding full bibliography for 7059847--7059851.cif.
;
_cod_database_code               7059850
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c28 h22 o4'
_reflns_odcompleteness_completeness 99.93
_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. Restrained distances
 O7-C61
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C53 \\sim O7 \\sim C61: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C58 \\sim O8 \\sim C62: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C50) = Uanis(C51) = Uanis(C52) = Uanis(C53) = Uanis(C54) = Uanis(C55) =
Uanis(C56) = Uanis(C57) = Uanis(C58) = Uanis(C59) = Uanis(C60)
4. Others
 Fixed Sof: O7(0.5) O8(0.5) C51(0.5) H51(0.5) C52(0.5) H52(0.5) C53(0.5)
 C54(0.5) H54(0.5) C55(0.5) H55(0.5) C56(0.5) H56(0.5) C57(0.5) H57(0.5)
 C58(0.5) C59(0.5) H59(0.5) C60(0.5) H60(0.5) C61(0.5) H61A(0.5) H61B(0.5)
 H61C(0.5) C62(0.5) H62A(0.5) H62B(0.5) H62C(0.5)
5.a Ternary CH refined with riding coordinates:
 C33(H33), C5AA(H5AA)
5.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C1AA(H1AA,H1AB)
5.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C38(H38), C39(H39), C40(H40), C44(H44), C45(H45), C46(H46),
 C47(H47), C48(H48), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56), C57(H57),
  C59(H59), C60(H60), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
5.d Fitted hexagon refined as free rotating group:
 C50(C51,C52,C53,C54,C55)
5.e Idealised Me refined with riding coordinates:
 C61(H61A,H61B,H61C), C62(H62A,H62B,H62C)
5.f Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'