Synthesis of Complex Bicyclic Scaffolds by Intermolecular Photosensitized Dearomative Cycloadditions of Activated Alkenes and Naphthalenes
Wang, Wang; Cai, Yanyao; Guo, Renyu; Brown, M. Kevin; Chemical Science  (2022) –; doi:10.1039/D2SC04789F

data_1567784
_publ_section_title
;
 Synthesis of Complex Bicyclic Scaffolds by Intermolecular Photosensitized
 Dearomative Cycloadditions of Activated Alkenes and Naphthalenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04789F
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H26 N O, Cl, 0.5(H2 O)'
_chemical_formula_sum            'C21 H27 Cl N O1.5'
_chemical_formula_weight         352.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.5120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0511(5)
_cell_length_b                   7.7600(3)
_cell_length_c                   17.0992(6)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.54
_cell_volume                     1888.96(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2019)'
_computing_data_collection       'BIS v6.2.14 (Bruker_AXS, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2019)'
_computing_molecular_graphics
;
C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX4 v2021.6-RC4 (Bruker AXS, 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
'1 deg frames measured 3 and 2 s, detector distance of 40 mm'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            75469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.372
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8672
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0754P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7487
_reflns_number_total             8672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04789f2.cif
_cod_data_source_block           22062
_cod_depositor_comments
;

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H54 Cl2 N2 O3'
_cod_original_formula_weight         705.77
_cod_original_formula_moiety         ' 2(C21 H26 N O), 2 Cl, H2 O'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567784
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              62706