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_1567728
_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 Cl O'
_chemical_formula_sum            'C20 H17 Cl O'
_chemical_formula_weight         308.79
_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             2022-05-19
_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                 115.798(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4028(2)
_cell_length_b                   19.5701(2)
_cell_length_c                   9.3681(2)
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.9920
_cell_measurement_theta_min      2.2490
_cell_volume                     1552.05(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  'SHELXL 2018/3 (Sheldrick, 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 0.885
_diffrn_measured_fraction_theta_max 0.880
_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     78.00 163.00   0.50    0.46    --   96.67  50.00 -91.00  170
  2  \w     99.00 164.00   0.50    0.46    --   96.67 117.00-150.00  130
  3  \w    105.00 170.00   0.50    0.46    --   96.67  96.00 120.00  130
  4  \w    106.00 171.00   0.50    0.46    --   96.67  97.00 131.00  130
  5  \w    -22.00  69.00   0.50    0.20    --   40.33 -81.00 -86.00  182
  6  \w     40.00  65.00   0.50    0.46    --   96.67 -97.00  23.00   50
  7  \w     -7.00  75.00   0.50    0.20    --   40.33 -97.00  23.00  164
  8  \w     28.00 125.00   0.50    0.46    --   96.67 -81.00 -86.00  194
  9  \w     29.00  83.00   0.50    0.46    --   96.67 -68.00-180.00  108
 10  \w     30.00  57.00   0.50    0.46    --   96.67 -50.00   0.00   54
 11  \w     30.00  57.00   0.50    0.46    --   96.67 -50.00  30.00   54
 12  \w     30.00  57.00   0.50    0.46    --   96.67 -50.00  60.00   54
 13  \w     30.00  57.00   0.50    0.46    --   96.67 -50.00  90.00   54
 14  \w     30.00  57.00   0.50    0.46    --   96.67 -50.00 122.00   54
 15  \w     29.00  83.00   0.50    0.46    --   96.67 -68.00  90.00  108
 16  \w    -26.00  57.00   0.50    0.20    --   40.33 -50.00 122.00  166
 17  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00   0.00  122
 18  \w    -74.00  29.00   0.50    0.20    --  -40.33  97.00 131.00  206
 19  \w    -81.00  -8.00   0.50    0.46    --  -82.50  97.00 131.00  146
 20  \w    -68.00  29.00   0.50    0.20    --  -40.33  81.00  36.00  194
 21  \w    -57.00  26.00   0.50    0.20    --  -40.33  50.00 -91.00  166
 22  \w    -57.00 -16.00   0.50    0.46    --  -82.50  50.00 -91.00   82
 23  \w   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00-150.00  162
 24  \w   -152.00 -78.00   0.50    0.46    --  -82.50 -81.00 -86.00  148
 25  \w   -156.00 -84.00   0.50    0.46    --  -82.50 -97.00  23.00  144
 26  \w   -149.00 -63.00   0.50    0.46    --  -82.50 -50.00 122.00  172
;
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8978
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         4.519
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71078
_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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+1.5930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           kmcke212_2
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_original_cell_volume        1552.05(5)
_cod_database_code               1567728
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.814
_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:
 C4(H4), C14(H14), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C16(H16), C12(H12), C17(H17), C20(H20), C19(H19), C8(H8),
 C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_shelx_res_checksum              8555
_shelx_hkl_checksum              72339
_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
;