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_1567944
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 O3'
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-05-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.11320(10)
_cell_length_b                   19.7985(2)
_cell_length_c                   5.92430(10)
_cell_measurement_reflns_used    14603
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      79.3750
_cell_measurement_theta_min      3.8320
_cell_volume                     1655.37(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      99.97(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 0.990
_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    101.00 178.00   0.50    0.14    --  113.25  30.00  30.00  154
  2  \w    101.00 178.00   0.50    0.14    --  113.25  45.00  90.00  154
  3  \w    102.00 178.00   0.50    0.14    --  113.25 113.00 -75.00  152
  4  \w    101.00 178.00   0.50    0.14    --  113.25  45.00 -90.00  154
  5  \w    100.00 125.00   0.50    0.14    --  113.25  15.00-180.00   50
  6  \w    -16.00  28.00   0.50    0.05    --  -47.32  19.00 120.00   88
  7  \w    -83.00 -19.00   0.50    0.14    --  -91.75 113.00 -75.00  128
  8  \w    -70.00  25.00   0.50    0.05    --  -47.32  76.00-154.00  190
  9  \w    -46.00 -19.00   0.50    0.14    --  -91.75  47.00  58.00   54
 10  \w   -163.00 -79.00   0.50    0.14    --  -91.75 -47.00 -90.00  168
 11  \w   -119.00 -73.00   0.50    0.05    --  -47.32-125.00-150.00   92
 12  \w   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00-180.00  188
 13  \w   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00-120.00  188
 14  \w   -120.00 -35.00   0.50    0.05    --  -47.32 -38.00 -60.00  170
 15  \w   -120.00 -35.00   0.50    0.05    --  -47.32 -38.00  30.00  170
 16  \w   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00  30.00  188
 17  \w   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00 120.00  188
 18  \w     42.00  79.00   0.50    0.14    --  113.25 -61.00-150.00   74
 19  \w     42.00 106.00   0.50    0.14    --  113.25 -94.00-120.00  128
 20  \w     42.00 114.00   0.50    0.14    --  113.25 -76.00  78.00  144
 21  \w     42.00  79.00   0.50    0.14    --  113.25 -61.00  30.00   74
 22  \w     42.00  79.00   0.50    0.14    --  113.25 -61.00 -90.00   74
 23  \w   -140.00-115.00   0.50    0.14    --  -91.75 -76.00  78.00   50
 24  \w    112.00 138.00   0.50    0.14    --  113.25  45.00 120.00   52
 25  \w    102.00 128.00   0.50    0.14    --  113.25  61.00  30.00   52
 26  \w    147.00 176.00   0.50    0.14    --  113.25  61.00  30.00   58
 27  \w     64.00 105.00   0.50    0.14    --  113.25 -94.00  90.00   82
 28  \w     42.00  67.00   0.50    0.14    --  113.25 -61.00 -60.00   50
 29  \w     49.00  99.00   0.50    0.14    --  113.25 -94.00 -90.00  100
 30  \w     80.00 106.00   0.50    0.14    --  113.25 -94.00-150.00   52
 31  \w     50.00  78.00   0.50    0.14    --  113.25 -61.00 150.00   56
;
_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      -0.0550468000
_diffrn_orient_matrix_UB_12      0.0509872000
_diffrn_orient_matrix_UB_13      -0.1464899000
_diffrn_orient_matrix_UB_21      -0.0921546000
_diffrn_orient_matrix_UB_22      -0.0396833000
_diffrn_orient_matrix_UB_23      0.0421164000
_diffrn_orient_matrix_UB_31      -0.0198592000
_diffrn_orient_matrix_UB_32      0.0433654000
_diffrn_orient_matrix_UB_33      0.2106530000
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19326
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.166
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87289
_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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0432P)^2^+0.2917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                3221
_reflns_number_total             3305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04750k2.cif
_cod_data_source_block           frojjh27
_cod_database_code               1567944
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.830
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              80791
_shelx_hkl_checksum              16833
_olex2_submission_original_sample_id frojjh27
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.731