Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis.
Tanaka, Kenta; Asada, Yosuke; Hoshino, Yujiro; Honda, Kiyoshi; Organic & biomolecular chemistry 18 (2020) 8074–8078; doi:10.1039/d0ob01151g

data_7157643
_publ_section_title
;
 Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic
 photoredox catalysis.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8074
_journal_page_last               8078
_journal_paper_doi               10.1039/d0ob01151g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C33 H24 Cl2 O4'
_chemical_formula_sum            'C33 H24 Cl2 O4'
_chemical_formula_weight         555.42
_chemical_name_systematic
(5aS*,8aR*,9R*)-8-(Bis(4-chlorophenyl)methylene)-9-(4-methoxyphenyl)-5a,8,8a,9-tetrahydrocyclopenta[b][1,3]dioxolo[4,5-g]chromene
_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     dual
_audit_creation_date             2019-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-16 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.126(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2283(2)
_cell_length_b                   9.87460(10)
_cell_length_c                   18.4264(2)
_cell_measurement_reflns_used    10771
_cell_measurement_temperature    123
_cell_measurement_theta_max      72.8310
_cell_measurement_theta_min      4.9710
_cell_volume                     2601.65(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_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    -10.00  17.00   0.50    0.77    --    0.00  19.00-150.00   54
  2  \w    -61.00  17.00   0.50    0.77    --    0.00 -57.00 -90.00  156
  3  \w    -73.00 -40.00   0.50    0.77    --    0.00 -19.00 150.00   66
  4  \w    -21.00  60.00   0.50    0.77    --    0.00  57.00 -90.00  162
  5  \w     11.00  55.00   0.50    3.07    --   91.80 -61.00-180.00   88
  6  \w     72.00 135.00   0.50    3.07    --   91.80  61.00 -30.00  126
  7  \w     63.00 102.00   0.50    3.07    --   91.80 -82.00 150.00   78
  8  \w     56.00 105.00   0.50    3.07    --   91.80 -30.00 -60.00   98
  9  \w     20.00  46.00   0.50    3.07    --   91.80 -30.00 -60.00   52
 10  \w      4.00 108.00   0.50    3.07    --   91.80 -82.00-120.00  208
 11  \w      2.00 109.00   0.50    3.07    --   91.80 -61.00-120.00  214
 12  \w     64.00 106.00   0.50    3.07    --   91.80 -82.00 120.00   84
 13  \w      3.00 105.00   0.50    3.07    --   91.80 -82.00-180.00  204
 14  \w     79.00 128.00   0.50    3.07    --   91.80  15.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0923152000
_diffrn_orient_matrix_UB_12      0.0774839000
_diffrn_orient_matrix_UB_13      0.0148960000
_diffrn_orient_matrix_UB_21      -0.0535662000
_diffrn_orient_matrix_UB_22      0.1352522000
_diffrn_orient_matrix_UB_23      -0.0124118000
_diffrn_orient_matrix_UB_31      0.0145082000
_diffrn_orient_matrix_UB_32      0.0060866000
_diffrn_orient_matrix_UB_33      0.0869437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16717
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.436
_diffrn_reflns_theta_min         4.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+1.1200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4755
_reflns_number_total             5075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01151g2.cif
_cod_data_source_block           exp_642
_cod_depositor_comments
'Adding full bibliography for 7157642--7157643.cif.'
_cod_database_code               7157643
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.628
_shelx_estimated_absorpt_t_min   0.628
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00C(H00C), C00R(H00R), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00B), C00E(H00E), C00H(H00H), C00J(H00J), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C012(H012)
2.d Idealised Me refined as rotating group:
 C013(H01C,H01D,H01E)
;
_shelx_res_checksum              88502
_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 3.219
_oxdiff_exptl_absorpt_empirical_full_min 0.332