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_7059847
_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         'C19 H16 O3'
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                73.411(9)
_cell_angle_beta                 81.291(9)
_cell_angle_gamma                89.961(6)
_cell_formula_units_Z            4
_cell_length_a                   9.9277(8)
_cell_length_b                   10.5377(6)
_cell_length_c                   15.220(2)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.9190
_cell_measurement_theta_min      3.2340
_cell_volume                     1506.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_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    -47.00  10.00   1.00   45.00    --  -15.36 -77.00 -60.00   57
  2  \w     38.00  81.00   1.00   45.00    --  -15.36 178.00-180.00   43
  3  \w    -23.00 101.00   1.00   45.00    --   15.99  38.00-180.00  124
  4  \w     35.00 113.00   1.00   45.00    --   15.99-178.00 120.00   78
  5  \w    -79.00  54.00   1.00   45.00    --   15.99 -77.00-120.00  133
  6  \w    -24.00  57.00   1.00   45.00    --   15.99  38.00 -60.00   81
  7  \w    -71.00  44.00   1.00   45.00    --   15.99 -57.00 120.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0699976000
_diffrn_orient_matrix_UB_12      0.0161211000
_diffrn_orient_matrix_UB_13      -0.0180971000
_diffrn_orient_matrix_UB_21      0.0160385000
_diffrn_orient_matrix_UB_22      -0.0200622000
_diffrn_orient_matrix_UB_23      0.0456863000
_diffrn_orient_matrix_UB_31      0.0088371000
_diffrn_orient_matrix_UB_32      -0.0654248000
_diffrn_orient_matrix_UB_33      -0.0031899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8268
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (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    1.289
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         8268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0716P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4731
_reflns_number_total             8268
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9064\% 
 around [0.97 -0.00 0.22] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
_cod_data_source_file            d0nj02923h2.cif
_cod_data_source_block           vhlphtmin
_cod_depositor_comments
;
 Adding full bibliography for 7059847--7059851.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H16 O3)'
_cod_original_formula_sum        'C38 H32 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     584.63
_cod_database_code               7059847
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c19 h17 o3'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6264(13)
 0.3736(13)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C33(H33),
  C34(H34), C37(H37)
3.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B), C38(H38A,H38B)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C35(H35A,H35B,H35C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.509
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2