Organophotoredox-Catalyzed Intermolecular Oxa-[4+2] Cycloaddition Reactions.
Tanaka, Kenta; Omata, Daichi; Asada, Yosuke; Hoshino, Yujiro; Honda, Kiyoshi; The Journal of organic chemistry 84 (2019) 10669–10678; doi:10.1021/acs.joc.9b01156

data_4033884
_publ_section_title
;
 Organophotoredox-Catalyzed Intermolecular Oxa-[4+2] Cycloaddition
 Reactions.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10669
_journal_page_last               10678
_journal_paper_doi               10.1021/acs.joc.9b01156
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H22 O5'
_chemical_formula_sum            'C24 H22 O5'
_chemical_formula_weight         390.41
_chemical_name_common
(6S*,8R*)-6,8-bis(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene
_chemical_name_systematic
(6S*,8R*)-6,8-bis(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.57920(10)
_cell_length_b                   9.54080(10)
_cell_length_c                   23.8992(3)
_cell_measurement_reflns_used    4553
_cell_measurement_temperature    223
_cell_measurement_theta_max      70.7280
_cell_measurement_theta_min      3.6890
_cell_volume                     1956.21(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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_temperature      223
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_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    -20.00   5.00   0.50    0.50    --  -20.00 -29.00-131.00   50
  2  \w      8.00  34.00   0.50    0.50    --   24.60  29.00  29.00   52
  3  \w    143.00 169.00   0.50    1.36    --  103.40 -29.00-131.00   52
  4  \w     18.00  44.00   0.50    0.50    --  -20.00  57.00-180.00   52
  5  \w    -65.00  17.00   0.50    0.50    --   24.60 -57.00 150.00  164
  6  \w     28.00  54.00   0.50    0.50    --   24.60 -57.00 150.00   52
  7  \w    -13.00  56.00   0.50    0.50    --   24.60 -57.00  60.00  138
  8  \w    -64.00 -27.00   0.50    0.50    --   24.60 -57.00  60.00   74
  9  \w     14.00  50.00   0.50    1.36    --  103.40 -50.00 120.00   72
 10  \w     26.00 123.00   0.50    1.36    --  103.40 -50.00-150.00  194
 11  \w     68.00 186.00   0.50    1.36    --  103.40  63.00   0.00  236
 12  \w     14.00 112.00   0.50    1.36    --  103.40 -82.00  30.00  196
 13  \w    118.00 143.00   0.50    1.36    --  103.40  50.00-150.00   50
 14  \w     91.00 130.00   0.50    1.36    --  103.40 -63.00  30.00   78
 15  \w     34.00  83.00   0.50    1.36    --  103.40 -63.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: 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      -0.1407020000
_diffrn_orient_matrix_UB_12      0.0370235000
_diffrn_orient_matrix_UB_13      -0.0372023000
_diffrn_orient_matrix_UB_21      0.0914218000
_diffrn_orient_matrix_UB_22      -0.0477306000
_diffrn_orient_matrix_UB_23      -0.0521020000
_diffrn_orient_matrix_UB_31      -0.0639131000
_diffrn_orient_matrix_UB_32      -0.1497879000
_diffrn_orient_matrix_UB_33      0.0074311000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6519
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.206
_diffrn_reflns_theta_min         3.699
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(18)
_refine_ls_extinction_coef       0.0005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0940P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                3207
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01156_si_001.cif
_cod_data_source_block           exp_166
_cod_database_code               4033884
_shelx_shelxl_version_number     2017/1
_publ_section_exptl
;
Any special experimental details
;
_diffrn_oxdiff_ac3_digest_frames
;
0186d64919481a311a1a928cb2fc09976700036a82d
;
_diffrn_oxdiff_ac3_digest_hkl
;
018cc93f69380b2e5426dd0060c9d9f8f56973
;
_reflns_odcompleteness_completeness 99.90
_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:
 C00B(H00B), C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00a,H00d)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J),
 C00L(H00L), C00O(H00O), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00Q(H00k,H00n,H00p), C00T(H00q,H00t,H00u)
;
_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 2.369
_oxdiff_exptl_absorpt_empirical_full_min 0.542