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_1573042
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.72327(3)
_cell_length_b                   7.75796(5)
_cell_length_c                   24.60196(14)
_cell_measurement_reflns_used    36233
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2960
_cell_measurement_theta_min      3.5730
_cell_volume                     1092.349(11)
_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 1.000
_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     46.00 118.00   0.50    2.16    --   52.65-146.00 175.00  144
  2  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -62.00  46.00  178
  3  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -62.00  46.00  178
  4  \w     46.00 127.00   0.50    6.29    --  102.45-146.00 175.00  162
  5  \w     86.00 176.00   0.50    6.29    --  102.45  58.00  -3.00  180
  6  \w     95.00 172.00   0.50    6.29    --  102.45 125.00  59.00  154
  7  \w   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00 -90.00   78
  8  \w   -122.00 -76.00   0.50    2.16    --  -53.15-125.00 -30.00   92
  9  \w   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00  90.00   78
 10  \w   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00 -30.00   78
 11  \w    -94.00  -4.00   0.50    2.16    --  -77.66  58.00  -3.00  180
 12  \w     89.00 178.00   0.50    6.29    --  102.45  45.00 -30.00  178
 13  \w     37.00 105.00   0.50    6.29    --  102.45 -95.00 -30.00  136
 14  \w     37.00 105.00   0.50    6.29    --  102.45 -95.00  30.00  136
 15  \w     95.00 172.00   0.50    6.29    --  102.45 125.00-150.00  154
 16  \w     30.00 119.00   0.50    6.29    --  102.45 -61.00-180.00  178
 17  \w     95.00 172.00   0.50    6.29    --  102.45 125.00-150.00  154
 18  \w     34.00 111.00   0.50    6.29    --  102.45-125.00 120.00  154
 19  \w     34.00 111.00   0.50    6.29    --  102.45-125.00 120.00  154
 20  \w     37.00 105.00   0.50    6.29    --  102.45 -95.00-180.00  136
 21  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -58.00-144.00  178
 22  \w   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00-150.00   78
 23  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 120.00  178
 24  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -60.00  178
 25  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00  90.00  178
 26  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -30.00  178
 27  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00   0.00  178
 28  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -90.00  178
 29  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00-180.00  178
 30  \w     80.00 169.00   0.50    6.29    --  102.45  77.00-150.00  178
 31  \w     86.00 175.00   0.50    6.29    --  102.45  61.00 120.00  178
 32  \w     80.00 169.00   0.50    6.29    --  102.45  77.00 -90.00  178
 33  \w     80.00 169.00   0.50    6.29    --  102.45  77.00-180.00  178
 34  \w     89.00 178.00   0.50    6.29    --  102.45  45.00  60.00  178
 35  \w     87.00 178.00   0.50    6.29    --  102.45  30.00-180.00  182
 36  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 -60.00  178
 37  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00  30.00  178
 38  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00-180.00  178
 39  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 150.00  178
 40  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00  30.00  178
 41  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00-120.00  178
 42  \w   -100.00 -11.00   0.50    2.16    --  -77.66  77.00-150.00  178
 43  \w   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 120.00  178
 44  \w     80.00 169.00   0.50    6.29    --  102.45  77.00-120.00  178
 45  \w     27.00 116.00   0.50    6.29    --  102.45 -45.00 -60.00  178
 46  \w     80.00 169.00   0.50    6.29    --  102.45  77.00   0.00  178
 47  \w     34.00 111.00   0.50    6.29    --  102.45-125.00 -60.00  154
 48  \w     80.00 169.00   0.50    6.29    --  102.45  77.00 -60.00  178
 49  \w     80.00 169.00   0.50    6.29    --  102.45  77.00 150.00  178
 50  \w     80.00 169.00   0.50    6.29    --  102.45  77.00  60.00  178
 51  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 -90.00  178
 52  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00   0.00  178
 53  \w   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00  90.00  178
 54  \w   -151.00 -61.00   0.50    2.16    --  -77.66 -58.00-144.00  180
 55  \w   -150.00 -85.00   0.50    2.16    --  -77.66 -61.00  60.00  130
 56  \w    -85.00 -13.00   0.50    2.16    --  -77.66 125.00   0.00  144
 57  \w     80.00 169.00   0.50    6.29    --  102.45  77.00 -30.00  178
 58  \w     80.00 169.00   0.50    6.29    --  102.45  77.00  90.00  178
 59  \w     80.00 169.00   0.50    6.29    --  102.45  77.00  30.00  178
 60  \w     34.00 111.00   0.50    6.29    --  102.45-125.00 -90.00  154
 61  \w     37.00 105.00   0.50    6.29    --  102.45 -95.00 120.00  136
 62  \w     80.00 169.00   0.50    6.29    --  102.45  77.00 120.00  178
 63  \w    -73.00 -48.00   0.50    2.16    --  -77.66  58.00  -3.00   50
 64  \w     55.00  80.00   0.50    2.16    --   50.32  58.00  -3.00   50
;
_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      0.0531136000
_diffrn_orient_matrix_UB_12      -0.0609992000
_diffrn_orient_matrix_UB_13      0.0582964000
_diffrn_orient_matrix_UB_21      -0.1779838000
_diffrn_orient_matrix_UB_22      0.1309677000
_diffrn_orient_matrix_UB_23      0.0224130000
_diffrn_orient_matrix_UB_31      -0.1947748000
_diffrn_orient_matrix_UB_32      -0.1362564000
_diffrn_orient_matrix_UB_33      -0.0045619000
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0075
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            46038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.502
_diffrn_reflns_theta_min         3.593
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_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    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_preparation
'The material was recrystallized from chloroform by slow evaporation'
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.0033(5)
_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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0317P)^2^+0.2487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2300
_reflns_number_total             2327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06684g2.cif
_cod_data_source_block           az14472834_100k_cu
_cod_depositor_comments
'Adding full bibliography for 1573041--1573042.cif.'
_cod_database_code               1573042
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.889
_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:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              77999
_shelx_hkl_checksum              68061
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_2283
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.847