Regioselective synthesis of N-containing polycyclic compounds <i>via</i> radical annulation cyclization of 1,7-dienes with aldehydes.
Sui, Jia-Li; Zhong, Long-Jin; Xiong, Bi-Quan; Tang, Ke-Wen; Liu, Yu; Chemical communications (Cambridge, England) 60 (2024) 4834–4837; doi:10.1039/d4cc00964a

data_7132951
_publ_section_title
;
 Regioselective synthesis of N-containing polycyclic compounds <i>via</i>
 radical annulation cyclization of 1,7-dienes with aldehydes.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4834
_journal_page_last               4837
_journal_paper_doi               10.1039/d4cc00964a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H22 Cl N O2'
_chemical_formula_sum            'C26 H22 Cl N O2'
_chemical_formula_weight         423.969
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-09 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                68.379(2)
_cell_angle_beta                 88.015(2)
_cell_angle_gamma                75.886(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7575(2)
_cell_length_b                   11.8553(3)
_cell_length_c                   12.4714(3)
_cell_measurement_reflns_used    9412
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      75.9650
_cell_measurement_theta_min      3.8000
_cell_volume                     1032.14(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_measured_fraction_theta_max 0.9509
_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     87.00 162.00   0.50    0.05    --  105.70 113.00 -33.00  150
  2  \w     31.00 104.00   0.50    0.05    --   45.99  57.00   0.00  146
  3  \w     94.00 120.00   0.50    0.05    --  105.70  30.00 120.00   52
  4  \w    123.00 148.00   0.50    0.05    --  105.70  30.00 120.00   50
  5  \w    102.00 159.00   0.50    0.05    --  105.70  30.00 -30.00  114
  6  \w     19.00  59.00   0.50    0.05    --   45.99 -57.00-120.00   80
  7  \w     39.00  74.00   0.50    0.05    --  105.70 -61.00-150.00   70
  8  \w     38.00  64.00   0.50    0.05    --  105.70 -61.00 -30.00   52
  9  \w     41.00 104.00   0.50    0.05    --  105.70 -77.00 120.00  126
 10  \w     75.00 101.00   0.50    0.05    --  105.70 -95.00  60.00   52
 11  \w     36.00  96.00   0.50    0.05    --  105.70-125.00 150.00  120
 12  \w     68.00 110.00   0.50    0.05    --  105.70-125.00  90.00   84
 13  \w     71.00 111.00   0.50    0.05    --  105.70-125.00  60.00   80
 14  \w     11.00  68.00   0.50    0.05    --   45.99-113.00-125.00  114
 15  \w     79.00 111.00   0.50    0.05    --  105.70-125.00-180.00   64
 16  \w     77.00 103.00   0.50    0.05    --  105.70 -95.00-180.00   52
 17  \w     81.00 108.00   0.50    0.05    --  105.70-113.00-125.00   54
 18  \w     51.00 105.00   0.50    0.05    --  105.70 -95.00 -90.00  108
 19  \w   -131.00 -78.00   0.50    0.05    -- -104.50 153.00-124.54  106
 20  \w    -83.00 -26.00   0.50    0.05    --  -45.99 113.00 -33.00  114
 21  \w    -79.00 -39.00   0.50    0.05    -- -104.50 125.00   0.00   80
 22  \w    -80.00 -44.00   0.50    0.05    -- -104.50 113.00 -33.00   72
 23  \w    -68.00 -43.00   0.50    0.05    -- -104.50  61.00 -90.00   50
 24  \w    -66.00 -31.00   0.50    0.05    -- -104.50  61.00-150.00   70
 25  \w    -67.00 -32.00   0.50    0.05    -- -104.50  61.00   0.00   70
 26  \w    -67.00 -42.00   0.50    0.05    -- -104.50  61.00 120.00   50
 27  \w    -23.00  26.00   0.50    0.05    --  -45.99  19.00 150.00   98
 28  \w   -105.00 -79.00   0.50    0.05    --  -45.99 -38.00   0.00   52
 29  \w    -64.00 -38.00   0.50    0.05    --  -45.99 -38.00   0.00   52
 30  \w   -120.00 -93.00   0.50    0.05    -- -104.50 -77.00  90.00   54
 31  \w   -169.00-141.00   0.50    0.05    -- -104.50 -77.00  90.00   56
 32  \w   -169.00 -87.00   0.50    0.05    -- -104.50 -61.00 -90.00  164
 33  \w   -115.00 -87.00   0.50    0.05    -- -104.50 -61.00 -60.00   56
 34  \w   -163.00-126.00   0.50    0.05    -- -104.50 -61.00 -60.00   74
 35  \w   -174.00 -94.00   0.50    0.05    -- -104.50 -45.00 150.00  160
 36  \w   -119.00 -35.00   0.50    0.05    --  -45.99 -38.00-150.00  168
 37  \w   -135.00 -81.00   0.50    0.05    -- -104.50-113.00-125.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1018228000
_diffrn_orient_matrix_UB_12      -0.1025657000
_diffrn_orient_matrix_UB_13      0.0245915000
_diffrn_orient_matrix_UB_21      -0.0650143000
_diffrn_orient_matrix_UB_22      0.0529126000
_diffrn_orient_matrix_UB_23      -0.1283944000
_diffrn_orient_matrix_UB_31      0.1658156000
_diffrn_orient_matrix_UB_32      -0.0866497000
_diffrn_orient_matrix_UB_33      -0.0251531000
_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  0.0152
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.9960
_diffrn_reflns_Laue_measured_fraction_max 0.9509
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11059
_diffrn_reflns_point_group_measured_fraction_full 0.9960
_diffrn_reflns_point_group_measured_fraction_max 0.9509
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.31
_diffrn_reflns_theta_min         3.82
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             450.011
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.3146
_refine_diff_density_min         -0.2333
_refine_diff_density_rms         0.0420
_refine_ls_d_res_high            0.7935
_refine_ls_d_res_low             11.5722
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0401
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0401
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.5037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3990
_reflns_number_total             4123
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc00964a2.cif
_cod_data_source_block           ZLJ03100K_auto
_cod_depositor_comments          'Adding full bibliography for 7132951.cif.'
_cod_original_cell_volume        1032.13(5)
_cod_database_code               7132951
_chemical_oxdiff_formula         'C N H'
_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 Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C16(H16), C17(H17), C15(H15), C14(H14), C5(H5), C2(H2), C22(H22),
 C1(H1), C25(H25), C23(H23), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C10(H10a,H10b,H10c)
;
_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.755