Synthesis of spirocyclic oxazole derivatives from 2-arylidene cycloalkanones and α-halohydroxamates
Wan, Huiyang; Xia, Shuangshuang; Liu, Xinghua; Jian, Yongchan; An, Yuanyuan; Wang, Yubin; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00701K

data_7158660
_publ_section_title
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 Synthesis of spirocyclic oxazole derivatives from 2-arylidene
 cycloalkanones and \a-halohydroxamates
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00701K
_journal_year                    2022
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.802(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.572(4)
_cell_length_b                   5.7581(6)
_cell_length_c                   18.4236(19)
_cell_measurement_reflns_used    3555
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.31
_cell_volume                     3714.1(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16826
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         2.266
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1309 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.7395.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0510P)^2^+2.0418P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3301
_reflns_number_total             4225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00701k2.cif
_cod_data_source_block           11_a
_cod_database_code               7158660
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.990
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C5(H5), C4(H4), C1(H1), C2(H2), C22(H22), C18(H18), C20(H20),
 C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              88271
_shelx_hkl_checksum              30240
_olex2_submission_special_instructions 'No special instructions were received'