Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives via Energy Transfer: A Method for Late-Stage Skeletal Transformation
Zhang, Zhijie; Yi, Dong; Zhang, Min; Wei, Jun; Lu, Ji; Yang, Lin; Wang, Jun; Hao, Na; Pan, Xianchao; Zhang, Shiqi; Wei, Siping; Fu, Qiang; ACS Catalysis  (2020) 10149–10156; doi:10.1021/acscatal.0c01841

data_4517988
_publ_section_title
;
 Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives
 via Energy Transfer: A Method for Late-Stage Skeletal Transformation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10149
_journal_page_last               10156
_journal_paper_doi               10.1021/acscatal.0c01841
_journal_year                    2020
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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     direct
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.992(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.31074(18)
_cell_length_b                   13.9007(3)
_cell_length_c                   8.86650(20)
_cell_measurement_reflns_used    4394
_cell_measurement_temperature    289.9(8)
_cell_measurement_theta_max      71.5750
_cell_measurement_theta_min      5.9130
_cell_volume                     1016.69(4)
_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_environment      air
_diffrn_ambient_temperature      289.9(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -90.00  -3.00   1.00    1.00    --  -36.29 126.00  50.00   87
  2  \w    -55.00  33.00   1.00    1.00    --  -36.29  38.00 -90.00   88
  3  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00-120.00   94
  4  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00 -60.00   94
  5  \w   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-150.00   84
  6  \w    -31.00  53.00   1.00    1.00    --   36.29 -57.00 150.00   84
  7  \w      1.00  75.00   1.00    1.00    --   36.29 -99.00  60.00   74
  8  \w     36.00 113.00   1.00    1.99    --  106.21-111.00  60.00   77
  9  \w     37.00 109.00   1.00    1.99    --  106.21 -94.00-150.00   72
 10  \w     38.00 124.00   1.00    1.99    --  106.21 -45.00  30.00   86
 11  \w     37.00 109.00   1.00    1.99    --  106.21 -94.00 120.00   72
 12  \w     36.00 128.00   1.00    1.99    --  106.21 -30.00-120.00   92
 13  \w     37.00 109.00   1.00    1.99    --  106.21 -94.00  90.00   72
 14  \w     36.00 128.00   1.00    1.99    --  106.21 -30.00 150.00   92
 15  \w     39.00 124.00   1.00    1.99    --  106.21 -61.00 150.00   85
 16  \w     88.00 173.00   1.00    1.99    --  106.21  61.00 150.00   85
 17  \w     88.00 173.00   1.00    1.99    --  106.21  61.00-150.00   85
 18  \w    100.00 176.00   1.00    1.99    --  106.21 111.00 -60.00   76
 19  \w     39.00 133.00   1.00    1.99    --  106.21 -77.00 -90.00   94
 20  \w     37.00 175.00   1.00    1.99    --  106.21   0.00   0.00  138
 21  \w    -90.00  -2.00   1.00    1.00    --  -36.29 125.00 -90.00   88
 22  \w   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00 120.00   84
 23  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00 120.00   94
 24  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00  30.00   94
 25  \w     20.00 104.00   1.00    1.00    --   36.29  57.00-150.00   84
 26  \w     17.00 105.00   1.00    1.00    --   36.29  38.00-150.00   88
 27  \w     68.00 170.00   1.00    1.99    --  106.21  15.00  90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213699000
_diffrn_orient_matrix_UB_12      -0.1083601000
_diffrn_orient_matrix_UB_13      0.0330264000
_diffrn_orient_matrix_UB_21      -0.0469182000
_diffrn_orient_matrix_UB_22      -0.0221641000
_diffrn_orient_matrix_UB_23      -0.1698876000
_diffrn_orient_matrix_UB_31      0.1795081000
_diffrn_orient_matrix_UB_32      0.0071269000
_diffrn_orient_matrix_UB_33      -0.0261744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.654
_diffrn_reflns_theta_min         5.951
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72730
_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    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0968P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1765
_reflns_number_total             1957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01841_si_002.cif
_cod_data_source_block           ydg-zzj-pi-o
_cod_depositor_comments
'Adding full bibliography for 4517987--4517988.cif.'
_cod_original_cell_volume        1016.68(4)
_cod_database_code               4517988
_reflns_odcompleteness_completeness 99.95
_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 Ternary CH refined with riding coordinates:
 C005(H005), C008(H008), C00A(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00C(H00E,H00F), C00E(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00D), C00D(H00G), C00F(H00J)
;
_shelx_res_checksum              52346
_shelx_hkl_checksum              32254
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-12-06
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.761