Alkynyl Prins Carbocyclization Cascades for the Synthesis of Linear-Fused Heterocyclic Ring Systems
Hernandez, Jackson; Frontier, Alison; Chemical Science  (2022) –; doi:10.1039/D2SC04750K

data_1567945
_publ_section_title
;
 Alkynyl Prins Carbocyclization Cascades for the Synthesis of Linear-Fused
 Heterocyclic Ring Systems
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04750K
_journal_year                    2022
_chemical_formula_moiety         'C22 H22 O3'
_chemical_formula_sum            'C22 H22 O3'
_chemical_formula_weight         334.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.5460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2159(2)
_cell_length_b                   10.13720(10)
_cell_length_c                   20.2267(2)
_cell_measurement_reflns_used    19642
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5630
_cell_measurement_theta_min      4.6590
_cell_volume                     3305.44(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -80.00  23.00   0.50    0.39    --  -47.16  99.00  -9.00  206
  2  \w     -1.00  81.00   0.50    0.39    --   47.16 -99.00-115.00  164
  3  \w   -163.00 -86.00   0.50    1.56    --  -91.75 -99.00-115.00  154
  4  \w    -80.00 -19.00   0.50    1.56    --  -91.75  99.00  -9.00  122
  5  \w     42.00 106.00   0.50    1.56    --  113.25 -99.00-115.00  128
  6  \w    107.00 178.00   0.50    1.56    --  113.25  99.00  -9.00  142
  7  \w    -35.00  26.00   0.50    0.39    --  -47.16  38.00 150.00  122
  8  \w    -35.00  26.00   0.50    0.39    --  -47.16  38.00  90.00  122
  9  \w   -119.00 -73.00   0.50    0.39    --  -47.16-125.00  30.00   92
 10  \w   -119.00 -73.00   0.50    0.39    --  -47.16-125.00  90.00   92
 11  \w    -16.00  28.00   0.50    0.39    --  -47.16  19.00 -90.00   88
 12  \w    -65.00 -19.00   0.50    1.56    --  -91.75  61.00-180.00   92
 13  \w     42.00  79.00   0.50    1.56    --  113.25 -61.00 120.00   74
 14  \w     42.00  79.00   0.50    1.56    --  113.25 -61.00   0.00   74
 15  \w     42.00  79.00   0.50    1.56    --  113.25 -61.00  30.00   74
 16  \w     97.00 178.00   0.50    1.56    --  113.25  61.00  30.00  162
 17  \w     42.00  79.00   0.50    1.56    --  113.25 -61.00-120.00   74
 18  \w    100.00 178.00   0.50    1.56    --  113.25  15.00 -90.00  156
 19  \w     42.00 106.00   0.50    1.56    --  113.25 -94.00 -60.00  128
 20  \w     42.00 106.00   0.50    1.56    --  113.25 -94.00 -30.00  128
 21  \w     42.00  79.00   0.50    1.56    --  113.25 -61.00 -90.00   74
 22  \w     42.00 111.00   0.50    1.56    --  113.25-125.00   0.00  138
 23  \w    111.00 178.00   0.50    1.56    --  113.25  30.00 150.00  134
 24  \w    122.00 178.00   0.50    1.56    --  113.25 125.00 -60.00  112
 25  \w     47.00  76.00   0.50    1.56    --  113.25 -61.00 -30.00   58
 26  \w     45.00  70.00   0.50    1.56    --  113.25 -61.00 -60.00   50
 27  \w     74.00 100.00   0.50    1.56    --  113.25 -94.00 120.00   52
 28  \w    117.00 143.00   0.50    1.56    --  113.25  45.00 -30.00   52
 29  \w    153.00 178.00   0.50    1.56    --  113.25  45.00 -30.00   50
 30  \w     42.00  75.00   0.50    1.56    --  113.25 -61.00  90.00   66
 31  \w     48.00  78.00   0.50    1.56    --  113.25 -61.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0156664000
_diffrn_orient_matrix_UB_12      0.0660534000
_diffrn_orient_matrix_UB_13      -0.0721380000
_diffrn_orient_matrix_UB_21      0.0260363000
_diffrn_orient_matrix_UB_22      -0.1281065000
_diffrn_orient_matrix_UB_23      -0.0275631000
_diffrn_orient_matrix_UB_31      -0.0905947000
_diffrn_orient_matrix_UB_32      -0.0481909000
_diffrn_orient_matrix_UB_33      -0.0255701000
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35734
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.392
_diffrn_reflns_theta_min         4.179
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0692P)^2^+0.9432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6280
_reflns_number_total             7100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04750k2.cif
_cod_data_source_block           frojjh25
_cod_database_code               1567945
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.891
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B),
 C29(H29A,H29B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C31(H31),
 C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              65945
_shelx_hkl_checksum              58820
_olex2_submission_original_sample_id frojjh25
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.721