Merging nucleophilic phosphine catalysis and photocatalysis for the rapid assembly of 2-oxabicyclo-[2.1.1]hexane scaffolds from feedstock allyl alcohols.
Whalley, David M.; Carlino, Luca; Putra, Okky Dwichandra; Anderson, Niall A.; Coote, Susannah C.; Lorthioir, Olivier; Chemical science 15 (2024) 19564–19570; doi:10.1039/d4sc06684g

data_1573041
_publ_section_title
;
 Merging nucleophilic phosphine catalysis and photocatalysis for the rapid
 assembly of 2-oxabicyclo-[2.1.1]hexane scaffolds from feedstock allyl
 alcohols.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              19564
_journal_page_last               19570
_journal_paper_doi               10.1039/d4sc06684g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2749(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.83321(10)
_cell_length_b                   6.75791(5)
_cell_length_c                   14.58577(12)
_cell_measurement_reflns_used    31963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6890
_cell_measurement_theta_min      3.1630
_cell_volume                     1119.652(16)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -23.00  65.00   0.50    1.16    --   52.65 -41.00  -0.00  176
  2  \w     41.00 129.00   0.50    1.16    --   52.65  41.00 153.00  176
  3  \w    -90.00  -1.00   0.50    1.16    --  -77.66  41.00 153.00  178
  4  \w    -90.00  -1.00   0.50    1.16    --  -77.66  41.00 153.00  178
  5  \w   -154.00 -65.00   0.50    1.16    --  -77.66 -41.00  -0.00  178
  6  \w     26.00 115.00   0.50    3.08    --  102.45 -41.00  -0.00  178
  7  \w     90.00 178.00   0.50    3.08    --  102.45  41.00 153.00  176
  8  \w     90.00 178.00   0.50    3.08    --  102.45  41.00 153.00  176
  9  \w    -19.00  20.00   0.50    1.16    --   18.00 100.00-157.87   78
 10  \w     -4.00  24.00   0.50    1.16    --   30.00  95.00-104.49   56
 11  \w     14.00  43.00   0.50    1.16    --   38.00  79.00 -83.88   58
 12  \w   -129.00 -41.00   0.50    1.16    --  -53.15 -41.00  -0.00  176
 13  \w    -65.00  23.00   0.50    1.16    --  -53.15  41.00 153.00  176
 14  \w   -129.00 -41.00   0.50    1.16    --  -53.15 -41.00  -0.00  176
 15  \w     38.00 127.00   0.50    1.16    --   58.00  72.00 -78.17  178
 16  \w   -145.00 -56.00   0.50    1.16    --  -74.00 -64.00-144.51  178
 17  \w    -94.00  -5.00   0.50    1.16    --  -77.66  61.00-120.00  178
 18  \w   -150.00 -61.00   0.50    1.16    --  -77.66 -61.00 -90.00  178
 19  \w   -143.00 -86.00   0.50    1.16    --  -77.66 -95.00 120.00  114
 20  \w   -156.00 -68.00   0.50    3.08    --  -86.25 -68.00-167.28  176
 21  \w   -155.00 -67.00   0.50    3.08    --  -86.25 -71.00-114.40  176
 22  \w   -156.00 -68.00   0.50    3.08    --  -86.25 -68.00-167.28  176
 23  \w     30.00 119.00   0.50    3.08    --  102.45 -61.00 150.00  178
 24  \w     80.00 169.00   0.50    3.08    --  102.45  77.00-120.00  178
 25  \w     54.00 178.00   0.50    3.08    --  102.45  15.00 -90.00  248
 26  \w     80.00 169.00   0.50    3.08    --  102.45  77.00 -60.00  178
 27  \w     86.00 175.00   0.50    3.08    --  102.45  61.00 -90.00  178
 28  \w     37.00 105.00   0.50    3.08    --  102.45 -95.00   0.00  136
 29  \w     95.00 172.00   0.50    3.08    --  102.45 125.00   0.00  154
 30  \w     37.00 105.00   0.50    3.08    --  102.45 -95.00  30.00  136
 31  \w     80.00 169.00   0.50    3.08    --  102.45  77.00 -90.00  178
 32  \w     80.00 169.00   0.50    3.08    --  102.45  77.00-150.00  178
 33  \w     86.00 175.00   0.50    3.08    --  102.45  61.00 -60.00  178
 34  \w     80.00 169.00   0.50    3.08    --  102.45  77.00-180.00  178
 35  \w     95.00 172.00   0.50    3.08    --  102.45 125.00  30.00  154
 36  \w     37.00 105.00   0.50    3.08    --  102.45 -95.00  90.00  136
 37  \w     95.00 172.00   0.50    3.08    --  102.45 125.00 120.00  154
 38  \w     86.00 175.00   0.50    3.08    --  102.45  61.00-120.00  178
 39  \w     34.00 111.00   0.50    3.08    --  102.45-125.00  90.00  154
 40  \w     37.00 105.00   0.50    3.08    --  102.45 -95.00-180.00  136
 41  \w     30.00 119.00   0.50    3.08    --  102.45 -61.00 150.00  178
 42  \w     86.00 175.00   0.50    3.08    --  102.45  61.00-120.00  178
 43  \w     95.00 172.00   0.50    3.08    --  102.45 125.00  60.00  154
 44  \w      5.00  32.00   0.50    1.16    --   34.00  87.00  28.73   54
 45  \w     13.00  41.00   0.50    1.16    --   38.00  80.00 125.42   56
 46  \w     13.00  39.00   0.50    1.16    --   38.00  81.00-153.26   52
 47  \w     15.00  43.00   0.50    1.16    --   38.00  78.00  44.57   56
 48  \w     43.00 131.00   0.50    1.16    --   62.00  71.00  -1.59  176
 49  \w     46.00 135.00   0.50    1.16    --   66.00  72.00  55.30  178
 50  \w   -140.00 -52.00   0.50    1.16    --  -70.00 -67.00 116.59  176
 51  \w   -141.00 -52.00   0.50    1.16    --  -70.00 -65.00 -55.09  178
 52  \w   -145.00 -56.00   0.50    1.16    --  -74.00 -66.00 -11.45  178
 53  \w   -145.00 -56.00   0.50    1.16    --  -74.00 -64.00  64.86  178
 54  \w   -100.00 -11.00   0.50    1.16    --  -77.66  77.00  30.00  178
 55  \w   -147.00 -59.00   0.50    1.16    --  -78.00 -71.00 152.06  176
 56  \w     86.00 175.00   0.50    3.08    --  102.45  61.00   0.00  178
 57  \w     80.00 169.00   0.50    3.08    --  102.45  77.00  30.00  178
 58  \w     80.00 169.00   0.50    3.08    --  102.45  77.00 -30.00  178
 59  \w     34.00 111.00   0.50    3.08    --  102.45-125.00 -30.00  154
 60  \w     80.00 169.00   0.50    3.08    --  102.45  77.00 150.00  178
 61  \w     80.00 169.00   0.50    3.08    --  102.45  77.00  60.00  178
 62  \w     80.00 169.00   0.50    3.08    --  102.45  77.00  90.00  178
 63  \w     41.00 135.00   0.50    3.08    --  107.25 -85.00 121.50  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0854757000
_diffrn_orient_matrix_UB_12      0.0274804000
_diffrn_orient_matrix_UB_13      -0.1004406000
_diffrn_orient_matrix_UB_21      0.0958399000
_diffrn_orient_matrix_UB_22      0.1135783000
_diffrn_orient_matrix_UB_23      -0.0312890000
_diffrn_orient_matrix_UB_31      0.0435955000
_diffrn_orient_matrix_UB_32      -0.1957517000
_diffrn_orient_matrix_UB_33      -0.0322325000
_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  0.0222
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.687
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_preparation
'The material was recrystallised from a mixture of acetonitrile and diethylether  by slow evaporation'
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of acetonitrile and diethylether  by slow evaporation'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0325P)^2^+0.4727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2310
_reflns_number_total             2383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06684g2.cif
_cod_data_source_block           az14466875_100k
_cod_depositor_comments
'Adding full bibliography for 1573041--1573042.cif.'
_cod_original_cell_volume        1119.653(17)
_cod_database_code               1573041
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     David
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.908
_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 Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              50359
_shelx_hkl_checksum              95891
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_2118
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.868