#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178437 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025829.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_4025829
loop_
_publ_author_name
'Karel Vervisch'
'Matthias D'hooghe'
'Karl W. Törnroos'
'Norbert De Kimpe'
_publ_section_title
;
 Synthesis of Stereodefined Piperidines from Aziridines and Their
 Transformation into Conformationally Constrained Amino Acids, Amino
 Alcohols and 2,7-Diazabicyclo[3.3.1]nonanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7734
_journal_page_last               7744
_journal_paper_doi               10.1021/jo101646u
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H23 Cl N2'
_chemical_formula_sum            'C21 H23 Cl N2'
_chemical_formula_weight         338.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.3122(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3116(3)
_cell_length_b                   8.7530(2)
_cell_length_c                   17.0047(4)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.40
_cell_volume                     1830.99(7)
_computing_cell_refinement       'Bruker SAINT v. 7.56A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT v. 7.56A'
_computing_molecular_graphics    'Bruker SHELXTL version 2008/4'
_computing_publication_material  'Bruker SHELXTL version 2008/4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean '24 \um'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30645
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.95355
_exptl_absorpt_correction_T_min  0.91012
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;  
Bruker AXS (2003). SHELXTL. Version 6.14. 
Bruker AXS Inc., Madison, Wisconsin, USA.  
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pinacoid
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.5173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                5333
_reflns_number_total             5650
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101646u_si_002.cif
_cod_data_source_block           Compound11b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025829
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.65462(2) 0.67580(2) 0.067410(14) 0.02797(7) Uani 1 1 d . . .
N1 N 0.75162(5) 0.34271(8) 0.07179(4) 0.01433(12) Uani 1 1 d . . .
C1 C 0.70237(6) 0.40228(9) 0.14289(4) 0.01445(13) Uani 1 1 d . . .
H1A H 0.7412 0.3548 0.1896 0.017 Uiso 1 1 calc R . .
N2 N 0.66352(7) 0.06044(10) 0.26787(5) 0.02818(17) Uani 1 1 d . . .
C2 C 0.58266(6) 0.35498(9) 0.14420(4) 0.01447(13) Uani 1 1 d . . .
H2A H 0.5426 0.4016 0.0986 0.017 Uiso 1 1 calc R . .
H2B H 0.5511 0.3951 0.1927 0.017 Uiso 1 1 calc R . .
C3 C 0.56732(6) 0.18058(8) 0.14126(4) 0.01360(13) Uani 1 1 d . . .
C4 C 0.62565(6) 0.12223(9) 0.06836(5) 0.01626(14) Uani 1 1 d . . .
H4A H 0.6234 0.0092 0.0673 0.020 Uiso 1 1 calc R . .
H4B H 0.5872 0.1604 0.0200 0.020 Uiso 1 1 calc R . .
C5 C 0.74324(6) 0.17553(9) 0.06967(5) 0.01652(14) Uani 1 1 d . . .
H5A H 0.7826 0.1323 0.1165 0.020 Uiso 1 1 calc R . .
H5B H 0.7783 0.1367 0.0223 0.020 Uiso 1 1 calc R . .
C6 C 0.71139(7) 0.57535(9) 0.15148(5) 0.01925(15) Uani 1 1 d . . .
H6A H 0.7890 0.6036 0.1593 0.023 Uiso 1 1 calc R . .
H6B H 0.6733 0.6077 0.1989 0.023 Uiso 1 1 calc R . .
C7 C 0.62105(7) 0.11273(9) 0.21287(5) 0.01819(15) Uani 1 1 d . . .
C8 C 0.86633(6) 0.38844(10) 0.06714(5) 0.01865(15) Uani 1 1 d . . .
H8A H 0.9085 0.3462 0.1129 0.022 Uiso 1 1 calc R . .
H8B H 0.8715 0.5012 0.0697 0.022 Uiso 1 1 calc R . .
C9 C 0.91522(6) 0.33310(9) -0.00767(5) 0.01550(14) Uani 1 1 d . . .
C10 C 0.87261(6) 0.38114(9) -0.08087(5) 0.01681(14) Uani 1 1 d . . .
H10A H 0.8124 0.4491 -0.0835 0.020 Uiso 1 1 calc R . .
C11 C 0.91742(7) 0.33052(10) -0.14990(5) 0.01877(15) Uani 1 1 d . . .
H11A H 0.8869 0.3637 -0.1992 0.023 Uiso 1 1 calc R . .
C12 C 1.00662(7) 0.23160(10) -0.14800(5) 0.02014(16) Uani 1 1 d . . .
C13 C 1.04934(7) 0.18435(10) -0.07499(6) 0.02160(16) Uani 1 1 d . . .
H13A H 1.1103 0.1177 -0.0723 0.026 Uiso 1 1 calc R . .
C14 C 1.00353(6) 0.23391(10) -0.00566(5) 0.01938(15) Uani 1 1 d . . .
H14A H 1.0331 0.1993 0.0436 0.023 Uiso 1 1 calc R . .
C15 C 1.05261(9) 0.17425(13) -0.22350(6) 0.0325(2) Uani 1 1 d . . .
H15A H 1.1262 0.1349 -0.2127 0.049 Uiso 1 1 calc R . .
H15B H 1.0552 0.2583 -0.2614 0.049 Uiso 1 1 calc R . .
H15C H 1.0063 0.0923 -0.2453 0.049 Uiso 1 1 calc R . .
C16 C 0.44831(6) 0.12966(9) 0.13869(4) 0.01397(13) Uani 1 1 d . . .
C17 C 0.42452(6) -0.02696(9) 0.14127(4) 0.01665(14) Uani 1 1 d . . .
H17A H 0.4821 -0.0990 0.1461 0.020 Uiso 1 1 calc R . .
C18 C 0.31740(7) -0.07776(10) 0.13683(5) 0.01936(15) Uani 1 1 d . . .
H18A H 0.3022 -0.1841 0.1386 0.023 Uiso 1 1 calc R . .
C19 C 0.23255(7) 0.02704(11) 0.12980(5) 0.02126(16) Uani 1 1 d . . .
H19A H 0.1594 -0.0075 0.1262 0.026 Uiso 1 1 calc R . .
C20 C 0.25542(7) 0.18235(10) 0.12803(5) 0.02102(16) Uani 1 1 d . . .
H20A H 0.1976 0.2541 0.1238 0.025 Uiso 1 1 calc R . .
C21 C 0.36293(6) 0.23384(9) 0.13249(5) 0.01760(15) Uani 1 1 d . . .
H21A H 0.3778 0.3403 0.1313 0.021 Uiso 1 1 calc R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 110.07(6) . . ?
C5 N1 C8 109.65(6) . . ?
C1 N1 C8 112.09(6) . . ?
N1 C1 C6 113.59(6) . . ?
N1 C1 C2 110.19(6) . . ?
C6 C1 C2 109.47(6) . . ?
N1 C1 H1A 107.8 . . ?
C6 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
C1 C2 C3 112.61(6) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C7 C3 C16 107.52(6) . . ?
C7 C3 C2 108.66(6) . . ?
C16 C3 C2 113.95(6) . . ?
C7 C3 C4 108.63(6) . . ?
C16 C3 C4 110.88(6) . . ?
C2 C3 C4 107.08(6) . . ?
C5 C4 C3 111.11(6) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C4 111.86(6) . . ?
N1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 Cl1 112.68(6) . . ?
C1 C6 H6A 109.1 . . ?
Cl1 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
Cl1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C3 179.34(9) . . ?
N1 C8 C9 111.96(6) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.38(7) . . ?
C14 C9 C8 121.18(7) . . ?
C10 C9 C8 120.44(7) . . ?
C11 C10 C9 120.63(7) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 121.08(8) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 118.23(8) . . ?
C13 C12 C15 121.24(8) . . ?
C11 C12 C15 120.50(9) . . ?
C12 C13 C14 120.67(8) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C14 C13 121.00(8) . . ?
C9 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.97(7) . . ?
C21 C16 C3 122.03(7) . . ?
C17 C16 C3 118.99(7) . . ?
C18 C17 C16 120.63(7) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 120.05(8) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C20 C19 C18 119.66(7) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.46(8) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C16 C21 C20 120.23(7) . . ?
C16 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.7957(9) . ?
N1 C5 1.4673(10) . ?
N1 C1 1.4698(9) . ?
N1 C8 1.4731(10) . ?
C1 C6 1.5255(11) . ?
C1 C2 1.5319(10) . ?
C1 H1A 1.0000 . ?
N2 C7 1.1481(12) . ?
C2 C3 1.5387(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.4860(11) . ?
C3 C16 1.5304(10) . ?
C3 C4 1.5444(10) . ?
C4 C5 1.5204(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.5090(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3907(11) . ?
C9 C10 1.3959(11) . ?
C10 C11 1.3896(11) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3978(12) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3915(13) . ?
C12 C15 1.5097(12) . ?
C13 C14 1.3964(12) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.3924(11) . ?
C16 C17 1.4029(10) . ?
C17 C18 1.3908(11) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3918(12) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3889(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3974(11) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C6 177.78(7) . . . . ?
C8 N1 C1 C6 55.47(9) . . . . ?
C5 N1 C1 C2 -58.98(8) . . . . ?
C8 N1 C1 C2 178.70(6) . . . . ?
N1 C1 C2 C3 58.16(8) . . . . ?
C6 C1 C2 C3 -176.24(6) . . . . ?
C1 C2 C3 C7 62.79(8) . . . . ?
C1 C2 C3 C16 -177.36(6) . . . . ?
C1 C2 C3 C4 -54.38(8) . . . . ?
C7 C3 C4 C5 -63.35(8) . . . . ?
C16 C3 C4 C5 178.71(6) . . . . ?
C2 C3 C4 C5 53.84(8) . . . . ?
C1 N1 C5 C4 60.36(8) . . . . ?
C8 N1 C5 C4 -175.89(6) . . . . ?
C3 C4 C5 N1 -58.75(8) . . . . ?
N1 C1 C6 Cl1 55.81(8) . . . . ?
C2 C1 C6 Cl1 -67.82(7) . . . . ?
C5 N1 C8 C9 60.00(9) . . . . ?
C1 N1 C8 C9 -177.44(6) . . . . ?
N1 C8 C9 C14 -119.08(8) . . . . ?
N1 C8 C9 C10 61.11(10) . . . . ?
C14 C9 C10 C11 0.15(11) . . . . ?
C8 C9 C10 C11 179.97(7) . . . . ?
C9 C10 C11 C12 -0.57(12) . . . . ?
C10 C11 C12 C13 0.27(12) . . . . ?
C10 C11 C12 C15 178.38(8) . . . . ?
C11 C12 C13 C14 0.45(12) . . . . ?
C15 C12 C13 C14 -177.65(8) . . . . ?
C10 C9 C14 C13 0.57(12) . . . . ?
C8 C9 C14 C13 -179.25(7) . . . . ?
C12 C13 C14 C9 -0.88(13) . . . . ?
C7 C3 C16 C21 125.89(8) . . . . ?
C2 C3 C16 C21 5.39(10) . . . . ?
C4 C3 C16 C21 -115.49(8) . . . . ?
C7 C3 C16 C17 -55.24(9) . . . . ?
C2 C3 C16 C17 -175.73(6) . . . . ?
C4 C3 C16 C17 63.38(9) . . . . ?
C21 C16 C17 C18 0.72(11) . . . . ?
C3 C16 C17 C18 -178.18(7) . . . . ?
C16 C17 C18 C19 -0.05(12) . . . . ?
C17 C18 C19 C20 -0.62(12) . . . . ?
C18 C19 C20 C21 0.62(13) . . . . ?
C17 C16 C21 C20 -0.72(11) . . . . ?
C3 C16 C21 C20 178.15(7) . . . . ?
C19 C20 C21 C16 0.06(13) . . . . ?
