Selective Radical Cascade (4+2) Annulation with Olefins towards the Synthesis of Chroman Derivatives via Organo-Photoredox Catalysis
Guan, Zhipeng; Zhong, Xingxing; Ye, Yayu; Li, Xiangwei; Cong, Hengjiang; Yi, Hong; Zhang, Heng; Huang, Zhiliang; Lei, Aiwen; Chemical Science  (2022) –; doi:10.1039/D2SC00903J

data_1566847
_publ_section_title
;
 Selective Radical Cascade (4+2) Annulation with Olefins towards the
 Synthesis of Chroman Derivatives via Organo-Photoredox Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00903J
_journal_year                    2022
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.7580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.77660(10)
_cell_length_b                   13.9140(2)
_cell_length_c                   21.1903(3)
_cell_measurement_reflns_used    13522
_cell_measurement_temperature    274(2)
_cell_measurement_theta_max      71.5480
_cell_measurement_theta_min      3.2140
_cell_volume                     2856.17(6)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 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    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      274(2)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -84.00  38.00   0.50    0.50    --    5.00 -57.00 -30.00  244
  2  \w    -32.00  94.00   0.50    0.50    --    5.00  38.00 -60.00  252
  3  \w    -80.00  42.00   0.50    0.50    --  -47.10  57.00-180.00  244
  4  \w   -136.00 -14.00   0.50    0.50    --  -47.10 -57.00  60.00  244
  5  \w   -130.00  -8.00   0.50    0.50    --  -97.00  57.00-150.00  244
  6  \w   -186.00 -64.00   0.50    0.50    --  -97.00 -57.00  90.00  244
  7  \w   -130.00  -8.00   0.50    0.50    --  -97.00  57.00  90.00  244
  8  \w   -186.00 -64.00   0.50    0.50    --  -97.00 -57.00 120.00  244
  9  \w   -186.00 -60.00   0.50    0.50    --  -97.00 -38.00   0.00  252
 10  \w   -186.00 -60.00   0.50    0.50    --  -97.00 -38.00 -30.00  252
 11  \w   -135.00  -8.00   0.50    0.50    --  -97.00  76.00-180.00  254
 12  \w   -186.00 -64.00   0.50    0.50    --  -97.00 -57.00 -60.00  244
 13  \w   -186.00 -59.00   0.50    0.50    --  -97.00 -76.00  90.00  254
 14  \w   -135.00  -8.00   0.50    0.50    --  -97.00  76.00 -90.00  254
 15  \w   -135.00  -8.00   0.50    0.50    --  -97.00  76.00-150.00  254
 16  \w   -186.00 -59.00   0.50    0.50    --  -97.00 -76.00 120.00  254
 17  \w   -136.00 -14.00   0.50    0.50    --  -47.10 -57.00-180.00  244
 18  \w   -136.00  -9.00   0.50    0.50    --  -47.10 -76.00-180.00  254
 19  \w   -136.00  -9.00   0.50    0.50    --  -47.10 -76.00   0.00  254
 20  \w   -136.00  -9.00   0.50    0.50    --  -47.10 -76.00 -60.00  254
 21  \w   -186.00 -84.00   0.50    0.50    --  -97.00 -57.00-150.00  204
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from \w-scans and \phi-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0407187000
_diffrn_orient_matrix_UB_12      -0.0445007000
_diffrn_orient_matrix_UB_13      -0.0664420000
_diffrn_orient_matrix_UB_21      0.0433712000
_diffrn_orient_matrix_UB_22      0.0932809000
_diffrn_orient_matrix_UB_23      -0.0310665000
_diffrn_orient_matrix_UB_31      0.1475205000
_diffrn_orient_matrix_UB_32      -0.0397131000
_diffrn_orient_matrix_UB_33      0.0014876000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            50596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.709
_diffrn_reflns_theta_min         3.811
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0693P)^2^+0.5031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4234
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00903j2.cif
_cod_data_source_block           law_zxx-159-7-20210524-rt
_cod_database_code               1566847
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'H C N O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     39.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C24(H24), C13(H13), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C19(H19), C4(H4), C1(H1A), C16(H16), C17(H17), C2(H2),
 C18(H18), C3(H3)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C11(H11A,H11B,H11C), C26(H26A,H26B,
 H26C), C15(H15A,H15B,H15C), C30(H30A,H30B,H30C), C14(H14A,H14B,H14C), C29(H29A,
 H29B,H29C)
;
_shelx_res_checksum              8234
_shelx_hkl_checksum              21451
_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 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.494