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_4038351
_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         'C37 H40 N4 O6 S2, 0.316(C H4 O)'
_chemical_formula_sum            'C37.32 H41.26 N4 O6.32 S2'
_chemical_formula_weight         710.98
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6020)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.410(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8945(9)
_cell_length_b                   21.4091(15)
_cell_length_c                   28.158(2)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.38
_cell_volume                     7125.6(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v.2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_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       '\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  0.0453
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            139564
_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         29.000
_diffrn_reflns_theta_min         1.944
_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    0.202
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.9593.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       tablet
_exptl_crystal_F_000             3006
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00100(16)
_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   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     962
_refine_ls_number_reflns         19071
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0455P)^2^+6.0690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15076
_reflns_number_total             19071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            20srv039.cif
_cod_data_source_block           20srv039
_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        7125.5(9)
_cod_database_code               4038351
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9863(3)
 0.0137(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.3 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 N1B-C8 \\sim N1A-C8
 with sigma of 0.02
 S1B-O1B \\sim S1A-O1A
 with sigma of 0.02
 S1B-N1B \\sim S1A-N1A
 with sigma of 0.02
 S1A-O2A \\sim S1B-O2B
 with sigma of 0.02
 S1B-C1B \\sim S1A-C1A
 with sigma of 0.02
 S2A-N2 \\sim S2B-N2
 with sigma of 0.02
 S2A-O4A \\sim S2B-O4B \\sim S2A-O3A \\sim S2B-O3B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(C1B) = Uanis(C1A)
Uanis(C7A) = Uanis(C7B)
Uanis(C4A) = Uanis(C4B)
Uanis(C3A) = Uanis(C3B)
Uanis(C6A) = Uanis(C6B)
Uanis(C5A) = Uanis(C5B)
Uanis(C2A) = Uanis(C2B)
Uanis(S2B) = Uanis(S2A)
Uanis(O4B) = Uanis(O4A)
Uanis(O3B) = Uanis(O3A)
Uanis(O2B) = Uanis(O2A)
5. Rigid body (RIGU) restrains
 N1A, S1A, O1A, O2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1B, S1B, O1B, O2B, C1B, C6B, C5B, C4B, C3B, C2B, C7B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H8A)=Sof(H8B)=Sof(S1B)=Sof(S2B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=
 Sof(N1B)=Sof(H1B)=Sof(C1B)=Sof(C6B)=Sof(H6B)=Sof(C5B)=Sof(H5B)=Sof(C4B)=
 Sof(C3B)=Sof(H3B)=Sof(C2B)=Sof(H2B)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H7BC)=1-
 FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(S1A)=Sof(S2A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=
 Sof(N1A)=Sof(H1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=
 Sof(O1S)=Sof(H1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=FVAR(1)
7.a Riding coordinates:
 N1A(H1A), C7A(H7AA,H7AB,H7AC), N1B(H1B), C7B(H7BA,H7BB,H7BC), O1S(H1S)
7.b Secondary CH2 refined with riding coordinates:
 C8'(H8'A,H8'B), C10'(H10A,H10B), C18'(H18A,H18B), C19'(H19A,H19B), C20'(H20A,
 H20B), C23'(H23A,H23B), C24'(H24A,H24B), C8(H8AA,H8AB), C8(H8A,H8B), C10(H10C,
 H10D), C18(H18C,H18D), C19(H19C,H19D), C20(H20C,H20D), C23(H23C,H23D),
 C24(H24C,H24D)
7.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'A), C3'(H3'), C5'(H5'), C6'(H6'), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C26'(H26'), C27'(H27'), C28'(H28'), C29'(H29'),
 C30'(H30'), C32'(H32'), C33'(H33'), C35'(H35'), C36'(H36'), C12(H12), C13(H13),
  C14(H14), C15(H15), C16(H16), C26(H26), C27(H27), C28(H28), C29(H29),
 C30(H30), C32(H32), C33(H33), C35(H35), C36(H36), C2A(H2A), C3A(H3A), C5A(H5A),
  C6A(H6A), C6B(H6B), C5B(H5B), C3B(H3B), C2B(H2B)
7.d Fitted hexagon refined as free rotating group:
 C1B(C6B,C5B,C4B,C3B,C2B)
7.e Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C37'(H37A,H37B,H37C), C37(H37D,H37E,H37F), C1S(H1SA,H1SB,
 H1SC)
;
_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   0.910
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              35473
_shelx_shelxl_version_number     2018/3