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_1567727
_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'
_chemical_formula_sum            'C23 H19 F N2 O'
_chemical_formula_weight         358.40
_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
_audit_creation_date             2022-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-20 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.6430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6548(4)
_cell_length_b                   7.2987(2)
_cell_length_c                   20.6049(6)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.38
_cell_volume                     1881.53(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.999
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0920 before and 0.0629 after correction. The Ratio of minimum to maximum transmission is 0.9485. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0632P)^2^+0.0436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2305
_reflns_number_total             3308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           prapd205b_0m_a
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_database_code               1567727
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.094) H3(0.087) H5(0.068) H6A(0.077) H6B(0.077) H7(0.064)
 H11(0.088) H12(0.089) H13(0.078) H14(0.063) H15(0.066) H18(0.098) H19(0.137)
 H20(0.132) H21(0.1) H22(0.086) H23A(0.127) H23B(0.127) H23C(0.127)
 Fixed X: H2(0.948142) H3(0.809817) H5(0.636085) H6A(0.63234) H6B(0.535054)
 H7(0.554952) H11(0.442838) H12(0.894745) H13(0.75834) H14(0.625211)
 H15(0.778248) H18(0.708154) H19(0.887914) H20(1.002209) H21(0.939459)
 H22(0.299015) H23A(0.235143) H23B(0.320614) H23C(0.235688)
 Fixed Y: H2(1.002918) H3(0.948924) H5(0.558766) H6A(0.925695) H6B(0.789744)
 H7(0.927048) H11(0.061432) H12(0.518979) H13(0.463741) H14(0.388741)
 H15(0.466661) H18(1.113524) H19(1.133254) H20(0.900536) H21(0.640379)
 H22(0.227237) H23A(0.549407) H23B(0.697526) H23C(0.634682)
 Fixed Z: H2(0.896472) H3(0.811599) H5(0.801176) H6A(0.779381) H6B(0.768177)
 H7(0.664282) H11(0.534175) H12(0.974858) H13(0.889443) H14(0.663289)
 H15(0.739593) H18(0.6297) H19(0.623056) H20(0.659451) H21(0.706259)
 H22(0.467281) H23A(0.455853) H23B(0.482249) H23C(0.525732)
;
_olex2_submission_special_instructions 'No special instructions were received'