#------------------------------------------------------------------------------
#$Date: 2019-11-04 14:32:28 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/45/4034522.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4034522
loop_
_publ_author_name
'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.'
_publ_section_title
;
 Far Away from Flatland. Synthesis and Molecular Structure of
 Dihetera[3.3.n]propellanes and Trihetera[3.3.n]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         'C10 H18 N O, Cl'
_chemical_formula_sum            'C10 H18 Cl N O'
_chemical_formula_weight         203.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 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            8
_cell_length_a                   24.981(5)
_cell_length_b                   7.1333(13)
_cell_length_c                   12.150(2)
_cell_measurement_reflns_used    1009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.63
_cell_measurement_theta_min      2.97
_cell_volume                     2165.1(7)
_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      296(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  0.0572
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23892
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.630
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1097P)²+0.7137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1958
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2709
_reflns_number_total             3907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02067_si_002.cif
_cod_data_source_block           xr126
_cod_original_cell_volume        2165.0(7)
_cod_database_code               4034522
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.4903(4) 0.4675(11) 0.3676(7) 0.069(2) Uani 1 1 d . .
H1A H 0.485492 0.346581 0.332414 0.083 Uiso 1 1 calc R U
H1B H 0.523802 0.465510 0.407950 0.083 Uiso 1 1 calc R U
C2 C 0.4913(3) 0.6237(9) 0.2806(6) 0.0487(17) Uani 1 1 d . .
C3 C 0.4678(3) 0.7848(11) 0.3498(6) 0.0478(18) Uani 1 1 d . .
C4 C 0.4283(4) 0.6905(12) 0.4249(8) 0.075(2) Uani 1 1 d . .
H4A H 0.426505 0.754987 0.495097 0.090 Uiso 1 1 calc R U
H4B H 0.392934 0.689539 0.392099 0.090 Uiso 1 1 calc R U
C5 C 0.5482(3) 0.6811(10) 0.2526(7) 0.057(2) Uani 1 1 d . .
H5A H 0.571922 0.573370 0.253941 0.068 Uiso 1 1 calc R U
H5B H 0.549805 0.738152 0.180234 0.068 Uiso 1 1 calc R U
C6 C 0.5170(3) 0.8595(11) 0.4101(8) 0.068(2) Uani 1 1 d . .
H6A H 0.513783 0.993546 0.421984 0.082 Uiso 1 1 calc R U
H6B H 0.520897 0.798286 0.480902 0.082 Uiso 1 1 calc R U
C7 C 0.4572(3) 0.5683(12) 0.1825(7) 0.067(2) Uani 1 1 d . .
H7A H 0.426016 0.500006 0.208119 0.080 Uiso 1 1 calc R U
H7B H 0.477646 0.485391 0.135147 0.080 Uiso 1 1 calc R U
C8 C 0.4389(4) 0.7387(15) 0.1161(8) 0.079(3) Uani 1 1 d . .
H8A H 0.469957 0.799122 0.083713 0.095 Uiso 1 1 calc R U
H8B H 0.415866 0.697441 0.056617 0.095 Uiso 1 1 calc R U
C9 C 0.4092(3) 0.8786(13) 0.1863(8) 0.078(2) Uani 1 1 d . .
H9A H 0.398312 0.984582 0.141534 0.093 Uiso 1 1 calc R U
H9B H 0.377233 0.820731 0.216333 0.093 Uiso 1 1 calc R U
C10 C 0.4446(3) 0.9449(10) 0.2785(7) 0.066(2) Uani 1 1 d . .
H10A H 0.424227 1.028434 0.325486 0.079 Uiso 1 1 calc R U
H10B H 0.474048 1.016306 0.247573 0.079 Uiso 1 1 calc R U
C11 C 0.3166(4) 0.3337(14) 0.2959(9) 0.091(3) Uani 1 1 d . .
H11A H 0.351917 0.343807 0.328643 0.110 Uiso 1 1 calc R U
H11B H 0.319197 0.262963 0.227899 0.110 Uiso 1 1 calc R U
C12 C 0.2783(3) 0.2464(11) 0.3727(7) 0.0496(19) Uani 1 1 d . .
C13 C 0.2534(3) 0.4018(9) 0.4399(6) 0.0478(16) Uani 1 1 d . .
C14 C 0.2518(5) 0.5559(15) 0.3471(9) 0.096(3) Uani 1 1 d . .
H14A H 0.217919 0.550900 0.308044 0.116 Uiso 1 1 calc R U
H14B H 0.255747 0.679771 0.378961 0.116 Uiso 1 1 calc R U
C15 C 0.2309(3) 0.1554(11) 0.3165(8) 0.071(2) Uani 1 1 d . .
H15A H 0.225480 0.209114 0.244035 0.085 Uiso 1 1 calc R U
H15B H 0.236709 0.021653 0.308631 0.085 Uiso 1 1 calc R U
C16 C 0.1986(3) 0.3367(10) 0.4710(7) 0.065(2) Uani 1 1 d . .
H16A H 0.173415 0.440218 0.469368 0.078 Uiso 1 1 calc R U
H16B H 0.198720 0.283102 0.544405 0.078 Uiso 1 1 calc R U
C17 C 0.3061(4) 0.0952(14) 0.4458(9) 0.081(3) Uani 1 1 d . .
H17A H 0.278921 0.017809 0.480153 0.097 Uiso 1 1 calc R U
H17B H 0.327825 0.014835 0.399363 0.097 Uiso 1 1 calc R U
C18 C 0.3410(4) 0.1785(15) 0.5339(10) 0.095(4) Uani 1 1 d . .
H18A H 0.354594 0.079417 0.580798 0.114 Uiso 1 1 calc R U
H18B H 0.371263 0.241187 0.500142 0.114 Uiso 1 1 calc R U
C19 C 0.3110(5) 0.3118(18) 0.5999(9) 0.103(4) Uani 1 1 d . .
H19A H 0.334375 0.363233 0.656096 0.123 Uiso 1 1 calc R U
H19B H 0.281966 0.246921 0.636625 0.123 Uiso 1 1 calc R U
C20 C 0.2868(3) 0.4811(15) 0.5274(8) 0.090(3) Uani 1 1 d . .
H20A H 0.265466 0.563088 0.573646 0.108 Uiso 1 1 calc R U
H20B H 0.315616 0.554233 0.495553 0.108 Uiso 1 1 calc R U
CL1 Cl 0.09501(8) 0.3140(2) 0.22955(16) 0.0657(6) Uani 1 1 d . .
CL2 Cl 0.14936(8) 0.8265(2) 0.49735(17) 0.0676(6) Uani 1 1 d . .
N1 N 0.5635(2) 0.8178(8) 0.3386(6) 0.0625(19) Uani 1 1 d . .
H1C H 0.590012 0.771165 0.379120 0.075 Uiso 1 1 calc R U
H1D H 0.574992 0.922997 0.307196 0.075 Uiso 1 1 calc R U
N2 N 0.1838(2) 0.1917(7) 0.3874(6) 0.0593(17) Uani 1 1 d . .
H2A H 0.173869 0.086404 0.420924 0.071 Uiso 1 1 calc R U
H2B H 0.156580 0.232227 0.346661 0.071 Uiso 1 1 calc R U
O1 O 0.4478(3) 0.5039(9) 0.4390(6) 0.092(2) Uani 1 1 d . .
O2 O 0.2931(3) 0.5192(12) 0.2769(7) 0.116(3) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 107.7(7)
C7 C2 C5 114.8(7)
C7 C2 C1 110.0(6)
C5 C2 C1 111.4(7)
C7 C2 C3 114.2(6)
C5 C2 C3 106.1(6)
C1 C2 C3 99.2(6)
C4 C3 C6 113.2(8)
C4 C3 C2 104.3(6)
C6 C3 C2 102.5(6)
C4 C3 C10 115.1(7)
C6 C3 C10 108.2(6)
C2 C3 C10 112.8(7)
O1 C4 C3 105.5(7)
N1 C5 C2 105.1(6)
N1 C6 C3 106.2(6)
C2 C7 C8 112.0(7)
C9 C8 C7 112.0(8)
C10 C9 C8 109.8(7)
C9 C10 C3 114.0(6)
O2 C11 C12 102.7(7)
C11 C12 C13 107.4(7)
C11 C12 C15 113.8(8)
C13 C12 C15 103.7(6)
C11 C12 C17 111.3(7)
C13 C12 C17 112.5(7)
C15 C12 C17 108.0(7)
C20 C13 C16 117.2(7)
C20 C13 C12 116.2(7)
C16 C13 C12 106.6(6)
C20 C13 C14 105.4(7)
C16 C13 C14 112.0(7)
C12 C13 C14 97.8(7)
O2 C14 C13 107.1(7)
N2 C15 C12 106.5(6)
C13 C16 N2 105.6(6)
C18 C17 C12 113.0(8)
C19 C18 C17 110.8(8)
C18 C19 C20 112.5(9)
C13 C20 C19 108.7(8)
C6 N1 C5 110.2(6)
C15 N2 C16 108.7(5)
C1 O1 C4 111.0(6)
C14 O2 C11 112.2(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.396(10)
C1 C2 1.536(10)
C2 C7 1.518(11)
C2 C5 1.519(10)
C2 C3 1.540(10)
C3 C4 1.503(12)
C3 C6 1.525(11)
C3 C10 1.545(11)
C4 O1 1.427(10)
C5 N1 1.479(11)
C6 N1 1.480(11)
C7 C8 1.529(13)
C8 C9 1.508(14)
C9 C10 1.505(12)
C11 O2 1.467(12)
C11 C12 1.475(12)
C12 C13 1.511(10)
C12 C15 1.513(11)
C12 C17 1.561(13)
C13 C20 1.465(11)
C13 C16 1.494(10)
C13 C14 1.575(12)
C14 O2 1.364(11)
C15 N2 1.479(10)
C16 N2 1.497(10)
C17 C18 1.501(14)
C18 C19 1.451(14)
C19 C20 1.613(15)
