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_1567725
_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         'C23 H19 F N2 O, C3 H7'
_chemical_formula_sum            'C26 H26 F N2 O'
_chemical_formula_weight         401.49
_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     iterative
_audit_creation_date             2022-05-18
_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                 107.152(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1117(2)
_cell_length_b                   20.3860(3)
_cell_length_c                   9.62050(10)
_cell_measurement_reflns_used    10887
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1240
_cell_measurement_theta_min      4.1550
_cell_volume                     2082.34(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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_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     25.00 109.00   0.50    0.29    --   41.33  43.00  30.00  168
  2  \w     70.00 165.00   0.50    1.15    --   96.67  77.00 -38.00  190
  3  \w     80.00 163.00   0.50    1.15    --   96.67  42.00 -60.00  166
  4  \w     83.00 164.00   0.50    1.15    --   96.67  33.00 -90.00  162
  5  \w     15.00 110.00   0.50    0.29    --   41.33  77.00 -38.00  190
  6  \w    -68.00  27.00   0.50    0.29    --  -41.33  77.00 -38.00  190
  7  \w    -24.00  35.00   0.50    0.29    --  -41.33  11.00-180.00  118
  8  \w    -28.00  30.00   0.50    0.29    --  -41.33  21.00 120.00  116
  9  \w     18.00  80.00   0.50    0.29    --   41.33-104.00  90.00  124
 10  \w     30.00 109.00   0.50    1.15    --   96.67-117.00 120.00  158
 11  \w     30.00 109.00   0.50    1.15    --   96.67-117.00  90.00  158
 12  \w     27.00 127.00   0.50    1.15    --   96.67 -87.00-180.00  200
 13  \w     28.00 105.00   0.50    1.15    --   96.67 -77.00-164.00  154
 14  \w     29.00  68.00   0.50    1.15    --   96.67 -59.00-120.00   78
 15  \w     29.00  83.00   0.50    1.15    --   96.67 -68.00 -60.00  108
 16  \w     30.00  57.00   0.50    1.15    --   96.67 -50.00 -90.00   54
 17  \w     30.00  57.00   0.50    1.15    --   96.67 -50.00-150.00   54
 18  \w     29.00  54.00   0.50    1.15    --   96.67 -59.00 -30.00   50
 19  \w     28.00 105.00   0.50    1.15    --   96.67 -77.00  90.00  154
 20  \w     29.00  68.00   0.50    1.15    --   96.67 -59.00 120.00   78
 21  \w   -110.00 -14.00   0.50    0.29    --  -41.33 -77.00-164.00  192
 22  \w   -149.00 -78.00   0.50    1.15    --  -82.50-117.00 -90.00  142
 23  \w   -151.00 -55.00   0.50    1.15    --  -82.50 -77.00-164.00  192
 24  \w    -47.00 -15.00   0.50    1.15    --  -82.50  42.00-150.00   64
 25  \w   -105.00 -14.00   0.50    1.15    --  -82.50  77.00 -38.00  182
 26  \w    -47.00 -15.00   0.50    1.15    --  -82.50  42.00 -30.00   64
 27  \w     81.00 164.00   0.50    1.15    --   96.67 145.00 -90.00  166
 28  \w     99.00 164.00   0.50    1.15    --   96.67 117.00 150.00  130
 29  \w    -30.00  28.00   0.50    0.29    --   41.33 -21.00   0.00  116
 30  \w    -27.00  68.00   0.50    0.29    --   41.33 -77.00-164.00  190
;
_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  0.0948
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15565
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_min         4.164
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90542
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0697P)^2^+0.6029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3355
_reflns_number_total             3735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           prapd203a_2
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_database_code               1567725
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.936
_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:
 C14(H14), C17(H17), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C26(H26a,H26b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C2(H2), C9(H9), C20(H20), C3(H3), C19(H19), C22(H22),
 C23(H23), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C24(H24a,H24b,H24c)
;
_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
;