Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis
Chuskit, Deachen; Chaudhary, Renu; Venugopalan, Paloth; König, Burkhard; Natarajan, Palani; Organic Chemistry Frontiers 5 (2018) 3553–; doi:10.1039/C8QO00792F

data_1554412
_publ_section_title
;
 Oxidative homodimerization of substituted olefins by DDQ visible light
 photocatalysis
;
_journal_issue                   24
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3553
_journal_paper_doi               10.1039/C8QO00792F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C28 H22'
_chemical_formula_sum            'C28 H22'
_chemical_formula_weight         358.45
_chemical_name_common            tetraarylethene
_chemical_name_systematic        tetraarylethene
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-25
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-29 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                100.341(4)
_cell_angle_beta                 103.170(4)
_cell_angle_gamma                95.285(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7638(5)
_cell_length_b                   10.0633(5)
_cell_length_c                   10.6246(5)
_cell_measurement_reflns_used    9100
_cell_measurement_temperature    122.98(13)
_cell_measurement_theta_max      66.5980
_cell_measurement_theta_min      4.3340
_cell_volume                     990.28(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.98(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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     15.00 117.00   1.00    1.00    --   40.89  37.00  60.00  102
  2  \w     11.00 115.00   1.00    1.00    --   40.89  57.00 -90.00  104
  3  \w    -33.00  70.00   1.00    1.00    --   40.89 -57.00 -30.00  103
  4  \w    -33.00  70.00   1.00    1.00    --   40.89 -57.00 150.00  103
  5  \w     11.00 115.00   1.00    1.00    --   40.89  57.00 120.00  104
  6  \w      4.00  32.00   1.00    1.00    --   42.00  90.00-115.84   28
  7  \w     11.00  40.00   1.00    1.00    --   46.00  83.00 127.13   29
  8  \w     19.00  45.00   1.00    1.00    --   54.00  82.00 -12.01   26
  9  \w     19.00  45.00   1.00    1.00    --   54.00  82.00 173.09   26
 10  \w     20.00  47.00   1.00    1.00    --   54.00  79.00  34.83   27
 11  \w     19.00  45.00   1.00    1.00    --   54.00  82.00 116.02   26
 12  \w     19.00  45.00   1.00    1.00    --   54.00  82.00 -61.56   26
 13  \w     28.00 141.00   1.00    1.00    --   62.00  77.00 -36.60  113
 14  \w     29.00 140.00   1.00    1.00    --   62.00  75.00-116.88  111
 15  \w     28.00 141.00   1.00    1.00    --   62.00  77.00  64.90  113
 16  \w     28.00 141.00   1.00    1.00    --   62.00  77.00 100.47  113
 17  \w     33.00 144.00   1.00    1.00    --   66.00  76.00-149.86  111
 18  \w     40.00 153.00   1.00    4.00    --   74.00  77.00 156.73  113
 19  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00 -60.00  113
 20  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00  90.00  113
 21  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00 120.00  113
 22  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00  60.00  113
 23  \w   -145.00 -49.00   1.00    4.00    --  -83.00 -77.00  30.00   96
 24  \w    -79.00 -51.00   1.00    4.00    --  -83.00 -77.00 -90.00   28
 25  \w    -77.00 -51.00   1.00    4.00    --  -83.00 -77.00-120.00   26
 26  \w    -76.00 -49.00   1.00    4.00    --  -83.00 -77.00-150.00   27
 27  \w    -77.00 -50.00   1.00    4.00    --  -83.00 -77.00 -30.00   27
 28  \w    -75.00 -49.00   1.00    4.00    --  -83.00 -77.00   0.00   26
 29  \w    -75.00 -49.00   1.00    4.00    --  -83.00 -77.00-180.00   26
 30  \w   -110.00 -85.00   1.00    4.00    --  -83.00  77.00-120.00   25
 31  \w     20.00  76.00   1.00    4.00    --   92.64 -45.00   0.00   56
 32  \w     62.00 156.00   1.00    4.00    --   92.64  77.00 -90.00   94
 33  \w     75.00 106.00   1.00    4.00    --   92.64 -77.00-120.00   31
 34  \w    114.00 140.00   1.00    4.00    --   92.64  61.00 -30.00   26
 35  \w     76.00 122.00   1.00    4.00    --   92.64  45.00 150.00   46
 36  \w     62.00 157.00   1.00    4.00    --   92.64  61.00   0.00   95
 37  \w     16.00  55.00   1.00    4.00    --   92.64 -77.00-120.00   39
 38  \w     36.00 120.00   1.00    4.00    --   92.64-125.00 150.00   84
 39  \w     74.00 151.00   1.00    4.00    --   92.64 125.00-150.00   77
 40  \w      8.00 102.00   1.00    4.00    --   92.64 -94.00   0.00   94
 41  \w      9.00 109.00   1.00    4.00    --   92.64 -94.00-150.00  100
 42  \w    122.00 149.00   1.00    4.00    --   92.64  77.00-180.00   27
 43  \w     60.00 150.00   1.00    4.00    --   92.64  77.00 150.00   90
 44  \w     59.00 119.00   1.00    4.00    --   92.64  77.00-180.00   60
 45  \w     68.00 158.00   1.00    4.00    --   92.64  77.00  90.00   90
 46  \w     78.00 156.00   1.00    4.00    --   92.64 125.00 -90.00   78
 47  \w     22.00  61.00   1.00    4.00    --   92.64 -45.00-120.00   39
 48  \w     67.00  92.00   1.00    4.00    --   92.64  61.00 -30.00   25
 49  \w     68.00 146.00   1.00    4.00    --   92.64  77.00  30.00   78
 50  \w     59.00 137.00   1.00    4.00    --   92.64  77.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0524666000
_diffrn_orient_matrix_UB_12      0.0057588000
_diffrn_orient_matrix_UB_13      -0.1468344000
_diffrn_orient_matrix_UB_21      -0.1241100000
_diffrn_orient_matrix_UB_22      0.0728536000
_diffrn_orient_matrix_UB_23      0.0310074000
_diffrn_orient_matrix_UB_31      0.0928367000
_diffrn_orient_matrix_UB_32      0.1391098000
_diffrn_orient_matrix_UB_33      0.0253939000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21623
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.631
_diffrn_reflns_theta_max         66.631
_diffrn_reflns_theta_min         4.368
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0500P)^2^+0.1826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2950
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00792f2.cif
_cod_data_source_block           q119
_cod_database_code               1554412
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C28 H22'
_chemical_oxdiff_usercomment     Natarajan_Koenig_PN-109
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C22(H22), C3(H3), C24(H24), C15(H15), C21(H21), C19(H19),
 C1(H1), C28(H28), C12(H12), C6(H6), C14(H14), C25(H25), C4(H4), C20(H20),
 C11(H11), C10(H10), C13(H13), C27(H27), C5(H5), C26(H26)
;
_olex2_date_sample_data_collection 2017-08-23
_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 1.530
_oxdiff_exptl_absorpt_empirical_full_min 0.675