A Mild Catalytic Synthesis of 2-Oxazolines via Oxetane Ring-Opening: Rapid Access to A Diverse Family of Natural Products
Huang, Hai; Yang, Wen; Zhang, Zuliang; Lai, Zengwei; Sun, Jianwei; Chemical Science  (2019) –; doi:10.1039/C9SC03843D

data_1552263
_publ_section_title
;
 A Mild Catalytic Synthesis of 2-Oxazolines via Oxetane Ring-Opening:
 Rapid Access to A Diverse Family of Natural Products
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03843D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 N O3 P'
_chemical_formula_sum            'C22 H20 N O3 P'
_chemical_formula_weight         377.36
_chemical_name_systematic
'(2-(4-(Hydroxymethyl)-4,5-dihydrooxazol-2-yl)phenyl)diphenylphosphine oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-04-07 deposited with the CCDC.    2019-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.158(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5956(3)
_cell_length_b                   9.7344(4)
_cell_length_c                   10.4231(4)
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7480
_cell_measurement_theta_min      4.2780
_cell_volume                     972.12(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_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    127.00 175.00   1.00   10.00    --  110.57  45.00 120.00   48
  2  \w    -66.00  37.00   1.00    3.00    --  -40.57  77.00-180.00  103
  3  \w    -70.00  31.00   1.00    3.00    --  -40.57  57.00 -30.00  101
  4  \w    -69.00  33.00   1.00    3.00    --  -40.57  77.00  60.00  102
  5  \w     84.00 111.00   1.00   10.00    --  110.57  45.00 120.00   27
  6  \w     67.00 169.00   1.00   10.00    --  110.57  15.00  60.00  102
  7  \w     81.00 163.00   1.00   10.00    --  110.57  61.00 -90.00   82
  8  \w     40.00 138.00   1.00   10.00    --  110.57 -45.00  90.00   98
  9  \w     64.00 138.00   1.00   10.00    --  110.57 -77.00 150.00   74
 10  \w     34.00 115.00   1.00   10.00    --  110.57-111.00 -30.00   81
 11  \w     37.00 108.00   1.00   10.00    --  110.57 -94.00  90.00   71
 12  \w     37.00 128.00   1.00   10.00    --  110.57 -45.00 -60.00   91
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589447000
_diffrn_orient_matrix_UB_12      -0.0085016000
_diffrn_orient_matrix_UB_13      0.1343434000
_diffrn_orient_matrix_UB_21      0.1495068000
_diffrn_orient_matrix_UB_22      -0.0062451000
_diffrn_orient_matrix_UB_23      0.0615277000
_diffrn_orient_matrix_UB_31      0.0027243000
_diffrn_orient_matrix_UB_32      0.1579164000
_diffrn_orient_matrix_UB_33      0.0096196000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5136
_diffrn_reflns_point_group_measured_fraction_full 0.688
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.488
_diffrn_reflns_theta_min         4.248
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.306
_reflns_Friedel_fraction_full    0.342
_reflns_Friedel_fraction_max     0.344
_reflns_number_gt                2247
_reflns_number_total             2411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03843d2.cif
_cod_data_source_block           zu1cult
_cod_database_code               1552263
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'P O N3 C24 H22'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.763
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              67153
_olex2_date_sample_data_collection 2017-09-04
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.690