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_4517987
_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         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.258(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2862(3)
_cell_length_b                   9.2093(2)
_cell_length_c                   13.1111(3)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.1830
_cell_measurement_theta_min      4.1000
_cell_volume                     1286.49(6)
_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      N~2~
_diffrn_ambient_temperature      150.00(10)
_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 0.985
_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    -53.00  33.00   1.00    1.00    --  -34.98  57.00 -60.00   86
  2  \w   -107.00   3.00   1.00    1.00    --  -34.98 -19.00 120.00  110
  3  \w     23.00  90.00   1.00    1.00    --   34.98-125.00-150.00   67
  4  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 120.00   67
  5  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00-120.00   74
  6  \w      6.00 104.00   1.00    1.00    --   34.98  77.00  30.00   98
  7  \w     37.00 110.00   1.00    1.03    --  106.90 -94.00 120.00   73
  8  \w     37.00 110.00   1.00    1.03    --  106.90 -94.00-180.00   73
  9  \w     37.00 127.00   1.00    1.03    --  106.90 -45.00 -60.00   90
 10  \w     61.00 178.00   1.00    1.03    --  106.90  15.00   0.00  117
 11  \w    100.00 178.00   1.00    1.03    --  106.90 111.00-150.00   78
 12  \w     78.00 176.00   1.00    1.03    --  106.90  77.00 120.00   98
 13  \w     35.00 133.00   1.00    1.03    --  106.90 -30.00 120.00   98
 14  \w    100.00 178.00   1.00    1.03    --  106.90 111.00-180.00   78
 15  \w   -106.00 -48.00   1.00    1.00    --  -34.98   0.00-150.00   58
 16  \w     16.00 103.00   1.00    1.00    --   34.98  57.00 -60.00   87
;
_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      0.0892708000
_diffrn_orient_matrix_UB_12      0.1145316000
_diffrn_orient_matrix_UB_13      0.0709294000
_diffrn_orient_matrix_UB_21      0.1129884000
_diffrn_orient_matrix_UB_22      -0.0797094000
_diffrn_orient_matrix_UB_23      -0.0152059000
_diffrn_orient_matrix_UB_31      -0.0131213000
_diffrn_orient_matrix_UB_32      0.0922061000
_diffrn_orient_matrix_UB_33      -0.1011782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.299
_diffrn_reflns_theta_min         4.149
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76280
_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    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0930P)^2^+0.2629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2226
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01841_si_003.cif
_cod_data_source_block           fq-zzj-pi-21-150
_cod_depositor_comments
'Adding full bibliography for 4517987--4517988.cif.'
_cod_original_cell_volume        1286.48(5)
_cod_database_code               4517987
_reflns_odcompleteness_completeness 100.00
_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:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00D(H00E,H00F), C00H(H00J,H00K), C00J(H00M,
 H00N), C00K(H00O,H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00G), C00F(H00H), C00G(H00I), C00I(H00L)
;
_shelx_res_checksum              42030
_shelx_hkl_checksum              8195
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-06-11
_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 1.722
_oxdiff_exptl_absorpt_empirical_full_min 0.719