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_4038353
_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         'C17 H18 Cl N O2 S'
_chemical_formula_sum            'C17 H18 Cl N O2 S'
_chemical_formula_weight         335.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.07.11 svn.r3635 for OlexSys, GUI svn.r5848)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.482(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0972(4)
_cell_length_b                   10.3026(4)
_cell_length_c                   16.9599(7)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.31
_cell_volume                     1586.63(11)
_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 multi-CPU (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 0.999
_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       \w-scan
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.142
_diffrn_reflns_theta_min         2.314
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
wR2(int) was 0.0722 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9684.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       irregular
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.199
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         6043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.5351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4563
_reflns_number_total             6043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5.cif
_cod_data_source_block           5_19s225
_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               4038353
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Others
 Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
 Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(2)
 Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(2)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=Uiso(H10D)=Uiso(H10E)=Uiso(H10F)=FVAR(3)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=Uiso(H17D)=Uiso(H17E)=Uiso(H17F)=FVAR(4)
2.a Disordered Me refined with riding coordinates:
 C10(H10A,H10B,H10C,H10D,H10E,H10F), C17(H17A,H17B,H17C,H17D,H17E,H17F)
;
_shelx_res_checksum              37881
_shelx_hkl_checksum              36072