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_4038348
_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         'C23 H27 Cl N2 O3 S'
_chemical_formula_sum            'C23 H27 Cl N2 O3 S'
_chemical_formula_weight         446.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-17
_audit_creation_method
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Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_b                   21.635(2)
_cell_length_c                   17.5661(16)
_cell_measurement_reflns_used    8733
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      2.22
_cell_volume                     2224.0(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'ShelXL 2018/3 multi-CPU version (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      230(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_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       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
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_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_k_min       -25
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_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35052
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
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_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) 
  was 0.1305 before and 0.0472 after correction. The Ratio of minimum to maximum 
  transmission is 0.9578. The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.227
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_refine_ls_extinction_coef       0.0093(8)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0423P)^2^+0.7924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00656_si_003.cif
_cod_data_source_block           19srv004
_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_original_cell_volume        2223.9(4)
_cod_database_code               4038348
_ccdc_polymorph                  'room temperature phase'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H7D)=Sof(H7E)=Sof(H7F)=1-FVAR(1)
 Sof(H7C)=Sof(H7A)=Sof(H7B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23)
3.c Disordered Me refined with riding coordinates:
 C7(H7C,H7A,H7B,H7D,H7E,H7F)
;
_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   0.899
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              3249
_shelx_shelxl_version_number     2018/3