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_1567943
_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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-02-03
_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                 100.5810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.11210(10)
_cell_length_b                   14.44820(10)
_cell_length_c                   11.06860(10)
_cell_measurement_reflns_used    13280
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.0630
_cell_measurement_theta_min      4.0280
_cell_volume                     1746.85(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.978
_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     25.00 120.00   0.50    0.06    --   47.26  77.00   0.00  190
  2  \w     25.00 120.00   0.50    0.06    --   47.26  77.00  30.00  190
  3  \w     25.00 120.00   0.50    0.06    --   47.26  77.00  90.00  190
  4  \w     25.00 120.00   0.50    0.06    --   47.26  77.00 -90.00  190
  5  \w     25.00 120.00   0.50    0.06    --   47.26  77.00-120.00  190
  6  \w     25.00 120.00   0.50    0.06    --   47.26  77.00-180.00  190
  7  \w     32.00 120.00   0.50    0.06    --   47.26  57.00-180.00  176
  8  \w     35.00 120.00   0.50    0.06    --   47.26  38.00 150.00  170
  9  \w    136.00 167.00   0.50    0.23    --  113.25 125.00  60.00   62
 10  \w    114.00 147.00   0.50    0.23    --  113.25 125.00  90.00   66
 11  \w    100.00 136.00   0.50    0.23    --  113.25 125.00   0.00   72
 12  \w    122.00 178.00   0.50    0.23    --  113.25 125.00 -30.00  112
 13  \w    153.00 178.00   0.50    0.23    --  113.25 125.00 -90.00   50
 14  \w     95.00 140.00   0.50    0.23    --  113.25 125.00 -90.00   90
 15  \w    106.00 178.00   0.50    0.23    --  113.25 102.00-153.00  144
 16  \w     98.00 131.00   0.50    0.23    --  113.25 125.00  60.00   66
 17  \w    115.00 169.00   0.50    0.23    --  113.25 125.00 150.00  108
 18  \w    114.00 169.00   0.50    0.23    --  113.25  82.00 124.34  110
 19  \w    100.00 144.00   0.50    0.23    --  113.25  15.00 120.00   88
 20  \w     93.00 119.00   0.50    0.23    --  113.25  77.00 120.00   52
 21  \w    121.00 147.00   0.50    0.23    --  113.25  77.00   0.00   52
 22  \w     91.00 118.00   0.50    0.23    --  113.25  77.00   0.00   54
 23  \w     93.00 135.00   0.50    0.23    --  113.25  77.00 -60.00   84
 24  \w     92.00 150.00   0.50    0.23    --  113.25  77.00-120.00  116
 25  \w     93.00 124.00   0.50    0.23    --  113.25  77.00-150.00   62
 26  \w    -73.00 -47.00   0.50    0.06    --  -47.27 102.00-153.00   52
 27  \w     56.00  87.00   0.50    0.23    --  113.25 -94.00 120.00   62
 28  \w     43.00  68.00   0.50    0.23    --  113.25 -61.00 150.00   50
 29  \w     42.00  73.00   0.50    0.23    --  113.25-125.00-120.00   62
 30  \w     76.00 109.00   0.50    0.23    --  113.25-125.00-120.00   66
 31  \w     53.00  79.00   0.50    0.23    --  113.25 -61.00 -90.00   52
 32  \w     42.00  68.00   0.50    0.23    --  113.25-125.00 -30.00   52
 33  \w     82.00 107.00   0.50    0.23    --  113.25-125.00 -30.00   50
 34  \w     47.00  73.00   0.50    0.23    --  113.25 -77.00  60.00   52
 35  \w     90.00 130.00   0.50    0.23    --  113.25 -77.00  60.00   80
 36  \w     58.00  84.00   0.50    0.23    --  113.25-102.00 103.00   52
 37  \w     62.00  88.00   0.50    0.23    --  113.25 -94.00-120.00   52
 38  \w     46.00  73.00   0.50    0.23    --  113.25 -61.00 120.00   54
;
_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      0.0649973000
_diffrn_orient_matrix_UB_12      -0.0926724000
_diffrn_orient_matrix_UB_13      -0.0133603000
_diffrn_orient_matrix_UB_21      0.1226717000
_diffrn_orient_matrix_UB_22      0.0428110000
_diffrn_orient_matrix_UB_23      0.0623318000
_diffrn_orient_matrix_UB_31      -0.0248320000
_diffrn_orient_matrix_UB_32      -0.0309813000
_diffrn_orient_matrix_UB_33      0.1263214000
_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  0.0366
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.156
_diffrn_reflns_theta_min         4.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89800
_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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0483P)^2^+0.7583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3460
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04750k2.cif
_cod_data_source_block           frojjh23
_cod_database_code               1567943
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.860
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-O1 \\sim C5-O1'
 with sigma of 0.01
 O1-C1 \\sim O1'-C1'
 with sigma of 0.01
 C1-C2 \\sim C1'-C2
 with sigma of 0.01
 C1-C22 \\sim C1'-C22'
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.4A with sigma of 0.005 and
sigma for terminal atoms of 0.01 within 1.4A
C22 \\sim C22': within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4. Others
 Sof(H2BC)=Sof(H2BD)=Sof(H5B)=Sof(O1')=Sof(C1')=Sof(H1')=Sof(C22')=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H2AA)=Sof(H2AB)=Sof(H5A)=Sof(O1)=Sof(C1)=Sof(H1)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Riding coordinates:
 C5(H5A), C5(H5B)
5.b Ternary CH refined with riding coordinates:
 C1(H1), C1'(H1')
5.c Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B)
5.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22'(H22D,H22E,H22F)
;
_shelx_res_checksum              2745
_shelx_hkl_checksum              80689
_olex2_submission_original_sample_id frojjh23
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.813