Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.<i>n</i>]propellanes and Trihetera[3.3.<i>n</i>]propellanes: Advanced Analogues of Morpholine/Piperazine.
Sokolenko, Yevhenii M.; Yurov, Yevhen Yu; Vashchenko, Bohdan V.; Hryshchuk, Oleksandr V.; Filimonova, Yuliia; Ostapchuk, Eugeniy N.; Artemenko, Artem; Zaremba, Oleg V.; Grygorenko, Oleksandr O.; The Journal of organic chemistry 84 (2019) 13908–13921; doi:10.1021/acs.joc.9b02067

data_4034520
_publ_section_title
;
 Far Away from Flatland. Synthesis and Molecular Structure of
 Dihetera[3.3.<i>n</i>]propellanes and Trihetera[3.3.<i>n</i>]propellanes:
 Advanced Analogues of Morpholine/Piperazine.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13908
_journal_page_last               13921
_journal_paper_doi               10.1021/acs.joc.9b02067
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C6 H12 N O, Cl'
_chemical_formula_sum            'C6 H12 Cl N O'
_chemical_formula_weight         149.62
_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   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 95.7031(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9635(2)
_cell_length_b                   6.8977(2)
_cell_length_c                   14.8768(4)
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.75
_cell_volume                     711.03(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9573
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         2.752
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0458P)^2^+0.1532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1209
_reflns_number_total             1482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02067_si_006.cif
_cod_data_source_block           xr186
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034520
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              75150
_shelx_hkl_checksum              3576