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_1552264
_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_formula_moiety         'C25 H26 N2 O4'
_chemical_formula_sum            'C25 H26 N2 O4'
_chemical_formula_weight         418.48
_chemical_name_systematic
(2,2'-(propane-2,2-diyl)bis(4,5-dihydrooxazole-4,2-diyl))dimethanol
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-10
_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                 106.293(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1435(3)
_cell_length_b                   10.3089(2)
_cell_length_c                   8.5206(2)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1370
_cell_measurement_theta_min      7.0960
_cell_volume                     1023.82(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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     96.00 122.00   1.00    3.00    --  106.99 -45.00-120.00   26
  2  \w    -19.00  30.00   1.00    2.00    --  -40.57  37.00 -90.00   49
  3  \w    -58.00 -24.00   1.00    2.00    --  -40.57  37.00 -90.00   34
  4  \w      1.00  83.00   1.00    2.00    --   40.57 -99.00  30.00   82
  5  \w      8.00  52.00   1.00    2.00    --   40.57 -99.00-180.00   44
  6  \w     34.00  93.00   1.00    3.00    --  106.99 -45.00-120.00   59
  7  \w     24.00  96.00   1.00    3.00    --  106.99 -94.00 150.00   72
  8  \w     87.00 173.00   1.00    3.00    --  106.99  61.00  30.00   86
  9  \w    102.00 177.00   1.00    3.00    --  106.99  61.00 -60.00   75
;
_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      -0.0682142000
_diffrn_orient_matrix_UB_12      0.0550387000
_diffrn_orient_matrix_UB_13      0.1127187000
_diffrn_orient_matrix_UB_21      -0.0942679000
_diffrn_orient_matrix_UB_22      -0.1024176000
_diffrn_orient_matrix_UB_23      -0.0649472000
_diffrn_orient_matrix_UB_31      0.0627154000
_diffrn_orient_matrix_UB_32      -0.0938265000
_diffrn_orient_matrix_UB_33      0.1362386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0055
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1521
_diffrn_reflns_point_group_measured_fraction_full 0.663
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         5.730
_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    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1226
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0230
_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^+0.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.284
_reflns_Friedel_fraction_full    0.315
_reflns_Friedel_fraction_max     0.311
_reflns_number_gt                1215
_reflns_number_total             1226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03843d2.cif
_cod_data_source_block           huang1cult
_cod_original_cell_volume        1023.82(5)
_cod_database_code               1552264
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.865
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              57094
_olex2_date_sample_data_collection 2019-01-08
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.777