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_4034518
_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_absolute_configuration ad
_chemical_formula_moiety         'C9 H16 N O, Cl'
_chemical_formula_sum            'C9 H16 Cl N O'
_chemical_formula_weight         189.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.468(3)
_cell_length_b                   10.606(6)
_cell_length_c                   12.627(4)
_cell_measurement_reflns_used    220
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      18.35
_cell_measurement_theta_min      3.17
_cell_volume                     1000.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7486
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_min         2.508
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                1127
_reflns_number_total             1782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02067_si_003.cif
_cod_data_source_block           xr125
_cod_database_code               4034518
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              90385
_shelx_hkl_checksum              43076