A rearrangement of 3-hydroxyazetidines into 2-oxazolines.
Ruggeri, Michele; Dombrowski, Amanda W.; Djuric, Stevan W.; Baxendale, Ian R.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00656

data_4038352
_publ_section_title
;
 A rearrangement of 3-hydroxyazetidines into 2-oxazolines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00656
_journal_year                    2020
_chemical_formula_moiety         'C24 H25 N O3 S2'
_chemical_formula_sum            'C24 H25 N O3 S2'
_chemical_formula_weight         439.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-28
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                69.0014(14)
_cell_angle_beta                 87.1419(16)
_cell_angle_gamma                87.6311(16)
_cell_formula_units_Z            4
_cell_length_a                   5.9971(2)
_cell_length_b                   19.0997(8)
_cell_length_c                   20.3305(8)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      29.69
_cell_measurement_theta_min      2.29
_cell_volume                     2170.67(15)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45131
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016) was used for absorption correction.
wR2(int) was 0.1478 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9480.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       lathe
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0022(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, 2015a)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         11184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.4806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8342
_reflns_number_total             11184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            19srv351.cif
_cod_data_source_block           19srv351
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038352
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(1)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2)
 Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(3)
 Uiso(H10D)=Uiso(H10E)=Uiso(H10F)=FVAR(4)
 Uiso(H17D)=Uiso(H17E)=Uiso(H17F)=FVAR(5)
 Uiso(H24D)=Uiso(H24E)=Uiso(H24F)=FVAR(6)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C1'(H1'A,H1'B), C3'(H3'A,H3'B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C21(H21), C22(H22), C23(H23), C5'(H5'), C6'(H6'), C8'(H8'), C9'(H9'),
  C12'(H12'), C13'(H13'), C15'(H15'), C16'(H16'), C19'(H19'), C21'(H21'),
 C22'(H22'), C23'(H23')
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C10'(H10D,H10E,
 H10F), C17'(H17D,H17E,H17F), C24'(H24D,H24E,H24F)
;
_oslims_operator_name            'Dr A Batsanov'
_oslims_operator_uuid            642c0cab-15e1-4db6-aabf-d1e3f44b6814
_oslims_submitter_name           'Mr Michele Ruggeri'
_oslims_submitter_uuid           1a56f251-525c-414f-9d37-3e740585b168
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              30622
_shelx_shelxl_version_number     2018/3