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_4038345
_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 O4 S'
_chemical_formula_sum            'C24 H25 N O4 S'
_chemical_formula_weight         423.51
_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
_audit_creation_date             2019-09-25
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.209(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9761(8)
_cell_length_b                   11.2566(8)
_cell_length_c                   17.2670(13)
_cell_measurement_reflns_used    4241
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.76
_cell_measurement_theta_min      2.75
_cell_volume                     2111.5(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0775
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         2.073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016) was used for absorption correction.
wR2(int) was 0.0616 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8988.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0044(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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+1.4751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2460
_reflns_number_total             3761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            19srv280.cif
_cod_data_source_block           19srv280
_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               4038345
_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 C(H,H,H) groups
2. Restrained distances
 O3C-C8C
 1.4 with sigma of 0.02
 C7C-C1B
 1.44 with sigma of 0.02
 O3C-C6B
 1.4 with sigma of 0.02
 C6B-O3C
 1.4 with sigma of 0.02
 C8C-C7C \\sim C8B-C7
 with sigma of 0.02
 C9B-C7C \\sim C9-C7
 with sigma of 0.02
 N-C9 \\sim N-C9B
 with sigma of 0.02
 O3A-C8A \\sim O3B-C8B
 with sigma of 0.02
 C8A-C7 \\sim C8B-C7
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C2B) = Uanis(C2A)
Uanis(C4B) = Uanis(C4A)
Uanis(O4B) = Uanis(O4A)
Uiso(C1B) = Uiso(C1A)
Uanis(C9B) = Uanis(C9)
Uiso(C8A) = Uiso(C8B)
Uanis(C3B) = Uanis(C3A)
Uanis(C5B) = Uanis(C5A)
4. Rigid body (RIGU) restrains
 O4A, C2A, C3A, C4A, C5A, C6A, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O4B, C2B, C3B, C4B, C5B, C6B, C7B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(1)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2)
 Fixed Sof: C7(0.95) C8B(0.283) H8BA(0.283) H8BB(0.283) C9B(0.05) H9BA(0.05)
 H9BB(0.05) O3A(0.667) O4A(0.667) C1A(0.667) C2A(0.667) C3A(0.667) H3A(0.667)
 C4A(0.667) C5A(0.667) H5A(0.667) C6A(0.667) H6A(0.667) C10A(0.667) H10A(0.667)
 H10B(0.667) H10C(0.667) O3B(0.283) O4B(0.333) C1B(0.333) C2B(0.333) C3B(0.333)
 H3B(0.333) C4B(0.333) C5B(0.333) H5B(0.333) C6B(0.333) H6B(0.333) C7B(0.333)
 H7BA(0.333) H7BB(0.333) H7BC(0.333) O3C(0.05) C8C(0.05) H8CA(0.05) H8CB(0.05)
 C7C(0.05) C9(0.95) H9A(0.95) H9B(0.95) C8A(0.667) H8AA(0.667) H8AB(0.667)
6.a Riding coordinates:
 C8B(H8BA,H8BB), C9B(H9BA,H9BB), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23), C3A(H3A), C5A(H5A), C6A(H6A), C3B(H3B),
  C5B(H5B), C6B(H6B), C8C(H8CA,H8CB), C9(H9A,H9B), C8A(H8AA,H8AB)
6.b Me refined with riding coordinates:
 C7B(H7BA,H7BB,H7BC)
6.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C10A(H10A,H10B,H10C)
;
_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   0.976
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              32258
_shelx_shelxl_version_number     2018/3