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_1567729
_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         'C22 H19 F O3'
_chemical_formula_sum            'C22 H19 F O3'
_chemical_formula_weight         350.37
_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     dual
_audit_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8641(2)
_cell_length_b                   10.52260(10)
_cell_length_c                   12.11710(10)
_cell_measurement_reflns_used    12932
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.0110
_cell_measurement_theta_min      3.2310
_cell_volume                     1722.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -81.00   1.00   0.50    0.23    --  -40.33 108.00 126.00  164
  2  \w     21.00  81.00   0.50    0.23    --   40.33-108.00  29.00  120
  3  \w   -152.00 -82.00   0.50    1.01    --  -82.50-108.00  29.00  140
  4  \w    -83.00 -13.00   0.50    1.01    --  -82.50 108.00 126.00  140
  5  \w    103.00 166.00   0.50    1.01    --   96.67 108.00 126.00  126
  6  \w     27.00 108.00   0.50    1.01    --   96.67-108.00  29.00  162
  7  \w    -24.00  35.00   0.50    0.23    --  -40.33  12.00  30.00  118
  8  \w    -43.00  26.00   0.50    0.23    --  -40.33  38.00 150.00  138
  9  \w    -31.00  30.00   0.50    0.23    --  -40.33  25.00  30.00  122
 10  \w   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00  30.00  182
 11  \w     25.00 111.00   0.50    0.23    --   40.33  25.00 150.00  172
 12  \w    -30.00  31.00   0.50    0.23    --   40.33 -25.00  30.00  122
 13  \w    -27.00  64.00   0.50    0.23    --   40.33 -64.00 -90.00  182
 14  \w    -47.00 -15.00   0.50    1.01    --  -82.50  42.00 -90.00   64
 15  \w    -47.00 -15.00   0.50    1.01    --  -82.50  42.00  60.00   64
 16  \w   -150.00 -69.00   0.50    1.01    --  -82.50 -33.00  60.00  162
 17  \w     83.00 164.00   0.50    1.01    --   96.67  33.00-180.00  162
 18  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00  90.00   54
 19  \w     82.00 167.00   0.50    1.01    --   96.67  25.00  30.00  170
 20  \w     29.00  68.00   0.50    1.01    --   96.67 -59.00  30.00   78
 21  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00   0.00   54
 22  \w     80.00 163.00   0.50    1.01    --   96.67  42.00  60.00  166
 23  \w     27.00 127.00   0.50    1.01    --   96.67 -87.00  30.00  200
 24  \w     82.00 167.00   0.50    1.01    --   96.67  25.00 -60.00  170
 25  \w     29.00  83.00   0.50    1.01    --   96.67 -68.00  60.00  108
 26  \w     30.00 109.00   0.50    1.01    --   96.67-117.00 120.00  158
 27  \w     81.00 164.00   0.50    1.01    --   96.67 145.00 -90.00  166
 28  \w     29.00  68.00   0.50    1.01    --   96.67 -59.00-150.00   78
 29  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00  60.00   54
 30  \w     29.00  68.00   0.50    1.01    --   96.67 -59.00  90.00   78
 31  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00-180.00   54
 32  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00 150.00   54
 33  \w   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00 -60.00  192
 34  \w    -78.00   4.00   0.50    0.23    --  -40.33 104.00 -90.00  164
 35  \w   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00   0.00  192
 36  \w   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00-120.00  192
 37  \w    -31.00  30.00   0.50    0.23    --  -40.33  25.00  90.00  122
 38  \w   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00 120.00  182
 39  \w   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00  90.00  192
 40  \w     21.00 107.00   0.50    0.23    --   40.33  50.00-120.00  172
 41  \w     14.00 109.00   0.50    0.23    --   40.33  77.00-120.00  190
 42  \w     17.00 108.00   0.50    0.23    --   40.33  64.00 -30.00  182
 43  \w     22.00 106.00   0.50    1.01    --   96.67 -96.00-150.00  168
 44  \w     78.00 163.00   0.50    1.01    --   96.67  50.00 120.00  170
 45  \w     83.00 164.00   0.50    1.01    --   96.67  33.00-120.00  162
 46  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00-120.00   54
 47  \w     30.00  57.00   0.50    1.01    --   96.67 -50.00 -90.00   54
 48  \w     75.00 148.00   0.50    1.01    --   96.67  59.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1032743000
_diffrn_orient_matrix_UB_12      0.0289310000
_diffrn_orient_matrix_UB_13      0.0211058000
_diffrn_orient_matrix_UB_21      0.0095339000
_diffrn_orient_matrix_UB_22      0.1391859000
_diffrn_orient_matrix_UB_23      -0.0354439000
_diffrn_orient_matrix_UB_31      -0.0474714000
_diffrn_orient_matrix_UB_32      -0.0349621000
_diffrn_orient_matrix_UB_33      -0.1238168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0517P)^2^+0.6784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2862
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           kmc-ke257_2_auto_2
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_database_code               1567729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.925
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C8(H8), C22(H22), C10(H10), C9(H9), C18(H18), C19(H19),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              40876
_shelx_hkl_checksum              29610
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.850