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_7159442
_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         'C19 H22 O3'
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                71.098(12)
_cell_angle_beta                 81.271(11)
_cell_angle_gamma                71.101(12)
_cell_formula_units_Z            2
_cell_length_a                   8.3025(12)
_cell_length_b                   9.7428(13)
_cell_length_c                   10.8769(13)
_cell_measurement_reflns_used    1108
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.0840
_cell_measurement_theta_min      4.2980
_cell_volume                     786.4(2)
_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 10.4115
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4305
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.570
_diffrn_reflns_theta_min         4.302
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.894
_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    1.260
_exptl_crystal_description       shards
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0035(7)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0403P)^2^+0.0962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1892
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00731f2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7159442--7159443.cif.'
_cod_database_code               7159442
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              5170