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_7157642
_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_absolute_configuration unk
_chemical_formula_moiety         'C33 H24 Cl2 O4, C3.5 H4'
_chemical_formula_sum            'C36.5 H28 Cl2 O4'
_chemical_formula_weight         601.49
_chemical_name_systematic
(5aR*,8aS*,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      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-16
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   59.6625(8)
_cell_length_b                   17.3644(2)
_cell_length_c                   11.02420(10)
_cell_measurement_reflns_used    12230
_cell_measurement_temperature    123
_cell_measurement_theta_max      72.7010
_cell_measurement_theta_min      4.7890
_cell_volume                     11421.1(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.964
_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    -50.00 -25.00   0.50    1.21    --    0.00 -47.00  -6.00   50
  2  \w     19.00  44.00   0.50    1.21    --    0.00  47.00 142.00   50
  3  \w     38.00  63.00   0.50    4.86    --   91.80 -47.00  -6.00   50
  4  \w    153.00 179.00   0.50    4.86    --   91.80  47.00 142.00   52
  5  \w    -34.00  13.00   0.50    1.21    --    0.00 -19.00-150.00   94
  6  \w    -88.00 -58.00   0.50    1.21    --    0.00 -19.00-150.00   60
  7  \w     33.00  72.00   0.50    4.86    --   91.80 -82.00 -90.00   78
  8  \w      2.00 107.00   0.50    4.86    --   91.80 -15.00   0.00  210
  9  \w    104.00 180.00   0.50    4.86    --   91.80  61.00 120.00  152
 10  \w     10.00 103.00   0.50    4.86    --   91.80 -30.00-180.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0139548000
_diffrn_orient_matrix_UB_12      0.0193876000
_diffrn_orient_matrix_UB_13      -0.1134724000
_diffrn_orient_matrix_UB_21      0.0196486000
_diffrn_orient_matrix_UB_22      0.0478062000
_diffrn_orient_matrix_UB_23      -0.0505798000
_diffrn_orient_matrix_UB_31      0.0092676000
_diffrn_orient_matrix_UB_32      -0.0721778000
_diffrn_orient_matrix_UB_33      -0.0639932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       72
_diffrn_reflns_limit_h_min       -73
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10848
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.369
_diffrn_reflns_theta_min         4.809
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77324
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             5008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0422P)^2^+12.0266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_full    0.609
_reflns_Friedel_fraction_max     0.562
_reflns_number_gt                4344
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01151g2.cif
_cod_data_source_block           exp_590
_cod_depositor_comments
'Adding full bibliography for 7157642--7157643.cif.'
_cod_original_formula_sum        'C36.50 H28 Cl2 O4'
_cod_database_code               7157642
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.647
_shelx_estimated_absorpt_t_min   0.647
_reflns_odcompleteness_completeness 99.19
_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. Others
 Fixed Sof: H01F(0.5) H01G(0.5) H01H(0.5)
3.a Ternary CH refined with riding coordinates:
 C00O(H00O), C00U(H00U), C010(H010)
3.b Secondary CH2 refined with riding coordinates:
 C016(H01A,H01B)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012), C013(H013),
 C015(H015)
3.d Idealised Me refined as rotating group:
 C017(H01C,H01D,H01E), C018(H01F,H01G,H01H)
;
_shelx_res_checksum              68386
_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.722