Synthesis of oxetane and azetidine ethers as ester isosteres by Brønsted acid catalysed alkylation of alcohols with 3-aryl-oxetanols and 3-aryl-azetidinols.
Saejong, Peerawat; Rojas, Juan J.; Denis, Camille; White, Andrew J. P.; Voisin-Chiret, Anne Sophie; Choi, Chulho; Bull, James A.; Organic & biomolecular chemistry 21 (2023) 5553–5559; doi:10.1039/d3ob00731f

data_7159443
_publ_section_title
;
 Synthesis of oxetane and azetidine ethers as ester isosteres by
 Br&#xf8;nsted acid catalysed alkylation of alcohols with 3-aryl-oxetanols
 and 3-aryl-azetidinols.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5553
_journal_page_last               5559
_journal_paper_doi               10.1039/d3ob00731f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-22 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.601(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   17.3283(6)
_cell_length_c                   8.0868(3)
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.8500
_cell_measurement_theta_min      2.8980
_cell_volume                     1415.22(10)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       tablets
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.604
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0124(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 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.4603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2479
_reflns_number_total             3171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00731f2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7159442--7159443.cif.'
_cod_original_cell_volume        1415.23(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159443
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              99852