Intermolecular dearomative [4 + 2] cycloaddition of naphthalenes via visible-light energy-transfer-catalysis
Rai, Pramod; Maji, Kakoli; Jana, Sayan K.; Maji, Biplab; Chemical Science 13 (2022) 12503–12510; doi:10.1039/D2SC04005K

data_1567726
_publ_section_title
;
 Intermolecular dearomative [4 + 2] cycloaddition of naphthalenes via
 visible-light energy-transfer-catalysis
;
_journal_issue                   42
_journal_name_full               'Chemical Science'
_journal_page_first              12503
_journal_page_last               12510
_journal_paper_doi               10.1039/D2SC04005K
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C20 H17 F O'
_chemical_formula_sum            'C20 H17 F O'
_chemical_formula_weight         292.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-05-19
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-19 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   38.8063(6)
_cell_length_b                   15.6732(3)
_cell_length_c                   9.8717(2)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.0230
_cell_measurement_theta_min      4.5460
_cell_volume                     6004.15(19)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.961
_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     25.00 106.00   0.50    3.03    --   40.33  39.00  24.00  162
  2  \w    117.00 155.00   0.50   11.00    --   96.67  39.00  24.00   76
  3  \w    111.00 163.00   0.50   11.00    --   96.67 117.00 -90.00  104
  4  \w    138.00 166.00   0.50   11.00    --   96.67  88.00-142.00   56
  5  \w    100.00 131.00   0.50   11.00    --   96.67  88.00-142.00   62
  6  \w     85.00 115.00   0.50   11.00    --   96.67  39.00  24.00   60
  7  \w     43.00  69.00   0.50   11.00    --   96.67 -68.00   0.00   52
  8  \w     34.00  77.00   0.50   11.00    --   96.67-108.00  14.00   86
  9  \w     52.00  88.00   0.50   11.00    --   96.67 -88.00 101.00   72
 10  \w     31.00  58.00   0.50    3.03    --   40.33-108.00  14.00   54
 11  \w     19.00  46.00   0.50    3.03    --   40.33 -88.00 101.00   54
 12  \w     32.00  57.00   0.50   11.00    --   96.67 -50.00  30.00   50
 13  \w     30.00  57.00   0.50   11.00    --   96.67 -50.00   0.00   54
 14  \w     30.00  55.00   0.50   11.00    --   96.67 -50.00 -30.00   50
 15  \w     29.00  67.00   0.50   11.00    --   96.67 -59.00-120.00   76
 16  \w     32.00  57.00   0.50   11.00    --   96.67 -50.00-180.00   50
 17  \w    -33.00  21.00   0.50    3.03    --   40.33 -12.00-180.00  108
 18  \w    -71.00  30.00   0.50    3.03    --  -40.33  88.00-142.00  202
 19  \w    -44.00  26.00   0.50    3.03    --  -40.33  39.00  24.00  140
 20  \w    -44.00 -19.00   0.50   11.00    --  -82.50  39.00  24.00   50
 21  \w    -72.00 -47.00   0.50   11.00    --  -82.50 108.00 111.00   50
 22  \w    -81.00   1.00   0.50    3.03    --  -40.33 108.00 111.00  164
 23  \w    -35.00   6.00   0.50    3.03    --   40.33 -12.00  90.00   82
 24  \w    -17.00  12.00   0.50    3.03    --   40.33 -88.00 101.00   58
 25  \w     30.00  55.00   0.50   11.00    --   96.67 -50.00 150.00   50
 26  \w     29.00  64.00   0.50   11.00    --   96.67 -59.00  90.00   70
 27  \w   -106.00 -25.00   0.50    3.03    --  -40.33 -39.00-129.00  162
 28  \w   -119.00 -92.00   0.50   11.00    --  -82.50 -39.00-129.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5410
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.162
_diffrn_reflns_theta_min         4.558
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 738 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+6.0426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.547
_reflns_Friedel_fraction_full    0.601
_reflns_Friedel_fraction_max     0.597
_reflns_number_gt                2111
_reflns_number_total             2167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           prapd208_2
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_database_code               1567726
_shelx_shelxl_version_number     2018/3
_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:
 C11(H11), C4(H4), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C20(H20), C6(H6), C7(H7), C16(H16), C8(H8), C19(H19),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              68421
_shelx_hkl_checksum              78821
_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
;