3-((Hetera)cyclobutyl)azetidines, "Stretched" Analogues of Piperidine, Piperazine, and Morpholine: Advanced Building Blocks for Drug Discovery.
Feskov, Illia O.; Chernykh, Anton V.; Kuchkovska, Yuliya O.; Daniliuc, Constantin G.; Kondratov, Ivan S.; Grygorenko, Oleksandr O.; The Journal of organic chemistry 84 (2019) 1363–1371; doi:10.1021/acs.joc.8b02822

data_4036040
_publ_section_title
;
 3-((Hetera)cyclobutyl)azetidines, &quot;Stretched&quot; Analogues of
 Piperidine, Piperazine, and Morpholine: Advanced Building Blocks for Drug
 Discovery.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1363
_journal_page_last               1371
_journal_paper_doi               10.1021/acs.joc.8b02822
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C13 H21 N O4'
_chemical_formula_weight         255.31
_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
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 98.378(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3322(4)
_cell_length_b                   16.0598(8)
_cell_length_c                   13.7532(7)
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.9568
_cell_measurement_theta_min      4.2587
_cell_volume                     1383.69(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;

APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12129
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0048P)^2^+2.1089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                1704
_reflns_number_total             2382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02822_si_001.cif
_cod_data_source_block           haf8688
_cod_database_code               4036040
_shelx_res_checksum              25904
_shelx_hkl_checksum              72629