#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150580.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_7150580
loop_
_publ_author_name
'Klein, Johannes E. M. N.'
'Müller-Bunz, Helge'
'Evans, Paul'
_publ_section_title
;
 Studies concerning the electrophilic amino-alkene cyclisation for the
 synthesis of bicyclic amines
;
_journal_issue                   5
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              986
_journal_page_last               995
_journal_paper_doi               10.1039/b819610a
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H24 N, Cl'
_chemical_formula_sum            'C17 H24 Cl N'
_chemical_formula_weight         277.82
_chemical_name_systematic
;
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 121.095(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.115(2)
_cell_length_b                   10.4898(13)
_cell_length_c                   10.9685(14)
_cell_measurement_reflns_used    1106
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.24
_cell_measurement_theta_min      2.17
_cell_volume                     1587.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4287
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.8410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.037 before and 0.028 after
correction. The Ratio of minimum to maximum transmission is 0.870192.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1664
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0432
_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)+(0.0584P)²+0.3286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                1444
_reflns_number_total             1664
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b819610a.txt
_cod_data_source_block           eva46
_cod_original_cell_volume        1587.7(4)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C17 H24 N Cl'
_cod_database_code               7150580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
N N 0.8913(2) 0.2486(3) 0.1573(3) 0.0492(9) Uani 1 1 d U . .
H1N H 0.8478 0.2816 0.0705 0.059 Uiso 1 1 calc R . .
C1 C 0.9467(3) 0.3598(5) 0.2481(4) 0.0684(12) Uani 1 1 d U . .
H1 H 0.9980 0.3264 0.3398 0.082 Uiso 1 1 calc R . .
C2 C 0.9943(4) 0.4324(5) 0.1836(7) 0.0992(19) Uani 1 1 d U . .
H2A H 1.0486 0.3833 0.1940 0.119 Uiso 1 1 calc R . .
H2B H 0.9485 0.4432 0.0825 0.119 Uiso 1 1 calc R . .
C3 C 1.0297(5) 0.5602(7) 0.2498(11) 0.165(4) Uani 1 1 d U . .
H3A H 1.0591 0.6039 0.2036 0.198 Uiso 1 1 calc R . .
H3B H 1.0785 0.5503 0.3498 0.198 Uiso 1 1 calc R . .
C4 C 0.9438(5) 0.6398(6) 0.2343(10) 0.153(3) Uani 1 1 d U . .
H4A H 0.9687 0.7134 0.2966 0.184 Uiso 1 1 calc R . .
H4B H 0.9050 0.6703 0.1372 0.184 Uiso 1 1 calc R . .
C5 C 0.8829(5) 0.5650(7) 0.2699(8) 0.122(2) Uani 1 1 d U . .
H5 H 0.8418 0.6109 0.2896 0.146 Uiso 1 1 calc R . .
C6 C 0.8795(4) 0.4448(5) 0.2772(5) 0.0823(15) Uani 1 1 d U . .
C7 C 0.8137(4) 0.3749(7) 0.3125(6) 0.1006(17) Uani 1 1 d U . .
H7A H 0.8517 0.3396 0.4077 0.121 Uiso 1 1 calc R . .
H7B H 0.7675 0.4345 0.3122 0.121 Uiso 1 1 calc R . .
C8 C 0.7616(4) 0.2733(5) 0.2131(5) 0.0775(14) Uani 1 1 d U . .
H8A H 0.7192 0.3086 0.1190 0.093 Uiso 1 1 calc R . .
H8B H 0.7220 0.2282 0.2420 0.093 Uiso 1 1 calc R . .
C9 C 0.8320(3) 0.1832(5) 0.2091(5) 0.0655(13) Uani 1 1 d U . .
H9A H 0.7970 0.1124 0.1464 0.079 Uiso 1 1 calc R . .
H9B H 0.8748 0.1492 0.3037 0.079 Uiso 1 1 calc R . .
C10 C 0.9529(3) 0.1549(4) 0.1311(4) 0.0460(10) Uani 1 1 d U . .
H10 H 0.9826 0.2035 0.0872 0.055 Uiso 1 1 calc R . .
C11 C 0.8883(3) 0.0551(4) 0.0232(4) 0.0586(12) Uani 1 1 d U . .
H11A H 0.9253 0.0071 -0.0070 0.088 Uiso 1 1 calc R . .
H11B H 0.8353 0.0965 -0.0576 0.088 Uiso 1 1 calc R . .
H11C H 0.8636 -0.0012 0.0660 0.088 Uiso 1 1 calc R . .
C12 C 1.0350(3) 0.1006(4) 0.2684(4) 0.0449(11) Uani 1 1 d U . .
C13 C 1.1278(3) 0.1508(4) 0.3259(4) 0.0534(11) Uani 1 1 d U . .
H13 H 1.1379 0.2171 0.2786 0.064 Uiso 1 1 calc R . .
C14 C 1.2051(3) 0.1052(5) 0.4507(5) 0.0638(13) Uani 1 1 d U . .
H14 H 1.2662 0.1412 0.4877 0.077 Uiso 1 1 calc R . .
C15 C 1.1915(4) 0.0069(5) 0.5200(5) 0.0675(13) Uani 1 1 d U . .
H15 H 1.2431 -0.0231 0.6056 0.081 Uiso 1 1 calc R . .
C16 C 1.1012(4) -0.0479(5) 0.4629(5) 0.0667(13) Uani 1 1 d U . .
H16 H 1.0922 -0.1166 0.5085 0.080 Uiso 1 1 calc R . .
C17 C 1.0238(3) -0.0010(4) 0.3378(5) 0.0584(12) Uani 1 1 d U . .
H17 H 0.9632 -0.0388 0.2999 0.070 Uiso 1 1 calc R . .
Cl Cl 0.76382(8) 0.35672(10) -0.14270(10) 0.0640(4) 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'
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
C1 N C9 112.4(3) . . ?
C1 N C10 114.0(3) . . ?
C9 N C10 112.2(3) . . ?
C1 N H1N 105.8 . . ?
C9 N H1N 105.8 . . ?
C10 N H1N 105.8 . . ?
C2 C1 N 111.0(4) . . ?
C2 C1 C6 112.8(5) . . ?
N C1 C6 110.1(3) . . ?
C2 C1 H1 107.6 . . ?
N C1 H1 107.6 . . ?
C6 C1 H1 107.6 . . ?
C3 C2 C1 112.8(6) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 109.6(5) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 111.6(6) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 127.6(7) . . ?
C6 C5 H5 116.2 . . ?
C4 C5 H5 116.2 . . ?
C5 C6 C7 124.4(7) . . ?
C5 C6 C1 119.9(7) . . ?
C7 C6 C1 115.7(5) . . ?
C8 C7 C6 112.3(4) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 109.6(4) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 N 111.2(4) . . ?
C8 C9 H9A 109.4 . . ?
N C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
N C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C12 C10 C11 114.3(3) . . ?
C12 C10 N 112.1(3) . . ?
C11 C10 N 109.9(3) . . ?
C12 C10 H10 106.7 . . ?
C11 C10 H10 106.7 . . ?
N C10 H10 106.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.4(4) . . ?
C17 C12 C10 123.1(4) . . ?
C13 C12 C10 119.5(4) . . ?
C14 C13 C12 121.8(4) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.1(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 121.1(4) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
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
N C1 1.494(6) . ?
N C9 1.506(5) . ?
N C10 1.526(5) . ?
N H1N 0.9100 . ?
C1 C2 1.494(7) . ?
C1 C6 1.558(7) . ?
C1 H1 0.9800 . ?
C2 C3 1.490(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.549(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.458(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.266(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.496(8) . ?
C7 C8 1.443(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.495(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.511(5) . ?
C10 C11 1.519(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.375(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.375(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N H1N Cl 0.91 2.16 3.058(3) 170.5 .
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
C9 N C1 C2 -172.7(4) . . . . ?
C10 N C1 C2 58.2(5) . . . . ?
C9 N C1 C6 -47.0(5) . . . . ?
C10 N C1 C6 -176.1(4) . . . . ?
N C1 C2 C3 166.0(4) . . . . ?
C6 C1 C2 C3 41.8(6) . . . . ?
C1 C2 C3 C4 -58.6(8) . . . . ?
C2 C3 C4 C5 45.2(10) . . . . ?
C3 C4 C5 C6 -17.7(11) . . . . ?
C4 C5 C6 C7 -179.1(7) . . . . ?
C4 C5 C6 C1 0.8(10) . . . . ?
C2 C1 C6 C5 -12.3(7) . . . . ?
N C1 C6 C5 -136.9(5) . . . . ?
C2 C1 C6 C7 167.6(4) . . . . ?
N C1 C6 C7 43.0(5) . . . . ?
C5 C6 C7 C8 131.0(6) . . . . ?
C1 C6 C7 C8 -48.9(6) . . . . ?
C6 C7 C8 C9 57.0(6) . . . . ?
C7 C8 C9 N -62.4(5) . . . . ?
C1 N C9 C8 58.5(5) . . . . ?
C10 N C9 C8 -171.5(3) . . . . ?
C1 N C10 C12 59.0(4) . . . . ?
C9 N C10 C12 -70.3(4) . . . . ?
C1 N C10 C11 -172.8(3) . . . . ?
C9 N C10 C11 58.0(4) . . . . ?
C11 C10 C12 C17 -42.8(5) . . . . ?
N C10 C12 C17 83.1(4) . . . . ?
C11 C10 C12 C13 134.3(4) . . . . ?
N C10 C12 C13 -99.8(4) . . . . ?
C17 C12 C13 C14 -2.9(6) . . . . ?
C10 C12 C13 C14 179.8(4) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C13 C14 C15 C16 1.5(7) . . . . ?
C14 C15 C16 C17 -1.9(7) . . . . ?
C13 C12 C17 C16 2.5(6) . . . . ?
C10 C12 C17 C16 179.7(4) . . . . ?
C15 C16 C17 C12 -0.2(7) . . . . ?
