Visible-light-induced intramolecular charge transfer in the radical spirocyclisation of indole-tethered ynones
Ho, Hon Eong; Pagano, Angela; Rossi-Ashton, James A.; Donald, James R.; Epton, Ryan G.; Churchill, Jonathan C.; James, Michael J.; O'Brien, Peter; Taylor, Richard J. K.; Unsworth, William P.; Chemical Science 11 (2020) 1353–1360; doi:10.1039/C9SC05311E

data_1556720
_publ_section_title
;
 Visible-light-induced intramolecular charge transfer in the radical
 spirocyclisation of indole-tethered ynones
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1353
_journal_page_last               1360
_journal_paper_doi               10.1039/C9SC05311E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.4536(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.42288(17)
_cell_length_b                   8.41061(12)
_cell_length_c                   28.0872(3)
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.8250
_cell_measurement_theta_min      4.5920
_cell_volume                     2653.64(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -25.00  20.00   1.00    1.00    --    0.00  37.00  60.00   45
  2  \w     42.00  68.00   1.00    1.00    --    0.00  37.00  60.00   26
  3  \w    -13.00  26.00   1.00    1.00    --    0.00  57.00-180.00   39
  4  \w     39.00  66.00   1.00    1.00    --    0.00  57.00-180.00   27
  5  \w     49.00  86.00   1.00    2.00    --   54.00  57.00-120.00   37
  6  \w     -9.00  83.00   1.00    2.00    --   54.00 -77.00   0.00   92
  7  \w     28.00 120.00   1.00    2.00    --   54.00  77.00 120.00   92
  8  \w     73.00 126.00   1.00    2.00    --   54.00  37.00-150.00   53
  9  \w     97.00 127.00   1.00    4.00    --  108.00 161.00-106.00   30
 10  \w     82.00 177.00   1.00    4.00    --  108.00  37.00-150.00   95
 11  \w     36.00 146.00   1.00    4.00    --  108.00 -91.00   0.00  110
 12  \w     87.00 168.00   1.00    4.00    --  108.00  63.00 120.00   81
 13  \w     74.00 126.00   1.00    4.00    --  108.00 -63.00 120.00   52
 14  \w    135.00 160.00   1.00    4.00    --  108.00 161.00-106.00   25
 15  \w    141.00 178.00   1.00    4.00    --  108.00 111.00  30.00   37
 16  \w    122.00 176.00   1.00    4.00    --  108.00  63.00 150.00   54
 17  \w     73.00 115.00   1.00    4.00    --  108.00 178.00-180.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382430000
_diffrn_orient_matrix_UB_12      -0.0933793000
_diffrn_orient_matrix_UB_13      0.0474352000
_diffrn_orient_matrix_UB_21      -0.0003485000
_diffrn_orient_matrix_UB_22      -0.1553655000
_diffrn_orient_matrix_UB_23      -0.0291016000
_diffrn_orient_matrix_UB_31      0.1317303000
_diffrn_orient_matrix_UB_32      0.0266480000
_diffrn_orient_matrix_UB_33      -0.0033158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'crystallisation from dichloromethane/hexane'
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00071(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0371P)^2^+0.7948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4079
_reflns_number_total             4722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05311e2.cif
_cod_data_source_block           rjkt1907
_cod_depositor_comments
;Adding full bibliography for 1556719--1556723.cif.

 Adding full bibliography for 1556719--1556723.cif.
;
_cod_original_cell_volume        2653.65(6)
_cod_database_code               1556720
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H13 N1 O1'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh260'
_reflns_odcompleteness_completeness 99.92
_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
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C1(H1A), C26(H26), C18(H18), C8(H8), C25(H25), C23(H23), C14(H14),
 C5(H5), C24(H24), C17(H17), C36(H36), C6(H6), C7(H7), C16(H16), C32(H32),
 C15(H15), C35(H35), C33(H33), C34(H34)
;
_shelx_res_checksum              30233
_olex2_date_sample_data_collection 2019-07-09
_olex2_date_sample_submission    2019-07-09
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id heh260
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.854