#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:44:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178404 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022569.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_4022569
loop_
_publ_author_name
'Gary A. Molander'
'Shawn K. Pack'
_publ_section_title
;
 Determining the Scope of the Organolanthanide-Catalyzed, Sequential
 Intramolecular Amination/Cyclization Reaction: Formation of Substituted
 Quinolizidines, Indolizidines, and Pyrrolizidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9214
_journal_page_last               9220
_journal_paper_doi               10.1021/jo035205f
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C11 H22 Cl N'
_chemical_formula_weight         203.75
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.273(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.515(3)
_cell_length_b                   7.061(2)
_cell_length_c                   16.081(4)
_cell_measurement_temperature    143(1)
_cell_volume                     1184.4(5)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi oscillations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6869
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.068
_refine_ls_goodness_of_fit_obs   1.125
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_restrained_S_obs      1.125
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_obs          0.0336
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0547P)²+0.2313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0948
_refine_ls_wR_factor_obs         0.0918
_reflns_number_observed          1833
_reflns_number_total             2154
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo035205fsi20030818_035018_2.cif
_cod_data_source_block           18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.37224(11) 0.7432(2) 0.59404(7) 0.0211(3) Uani 1 d .
H1 H 0.37567(11) 0.8720(2) 0.59334(7) 0.028 Uiso 1 calc R
C2 C 0.2880(2) 0.6784(2) 0.51682(9) 0.0280(3) Uani 1 d .
H2A H 0.2893(2) 0.5412(2) 0.51420(9) 0.037 Uiso 1 calc R
H2B H 0.3216(2) 0.7269(2) 0.46755(9) 0.037 Uiso 1 calc R
C3 C 0.1512(2) 0.7452(2) 0.51625(10) 0.0323(4) Uani 1 d .
H3A H 0.0992(2) 0.6962(2) 0.46683(10) 0.043 Uiso 1 calc R
H3B H 0.1488(2) 0.8824(2) 0.51339(10) 0.043 Uiso 1 calc R
C4 C 0.09541(15) 0.6797(2) 0.59447(10) 0.0290(3) Uani 1 d .
H4 H 0.09598(15) 0.5410(2) 0.59553(10) 0.039 Uiso 1 calc R
C5 C 0.18255(14) 0.7514(2) 0.67118(9) 0.0234(3) Uani 1 d .
H5A H 0.18198(14) 0.8887(2) 0.67109(9) 0.031 Uiso 1 calc R
H5B H 0.14895(14) 0.7091(2) 0.72148(9) 0.031 Uiso 1 calc R
C6 C 0.31979(13) 0.6822(2) 0.67332(8) 0.0198(3) Uani 1 d .
H6 H 0.31967(13) 0.5435(2) 0.67547(8) 0.026 Uiso 1 calc R
C7 C 0.40887(14) 0.7555(2) 0.74792(9) 0.0258(3) Uani 1 d .
H7A H 0.37560(14) 0.7196(2) 0.79925(9) 0.034 Uiso 1 calc R
H7B H 0.41178(14) 0.8927(2) 0.74569(9) 0.034 Uiso 1 calc R
C8 C 0.54431(15) 0.6766(2) 0.74905(10) 0.0340(4) Uani 1 d .
H8A H 0.54254(15) 0.5401(2) 0.75578(10) 0.045 Uiso 1 calc R
H8B H 0.59932(15) 0.7290(2) 0.79644(10) 0.045 Uiso 1 calc R
C9 C 0.59920(15) 0.7253(2) 0.66783(11) 0.0337(4) Uani 1 d .
H9 H 0.67609(15) 0.6473(2) 0.66679(11) 0.045 Uiso 1 calc R
C10 C 0.50562(14) 0.6680(2) 0.59229(10) 0.0282(3) Uani 1 d .
H10A H 0.53763(14) 0.7133(2) 0.54191(10) 0.038 Uiso 1 calc R
H10B H 0.50199(14) 0.5309(2) 0.58935(10) 0.038 Uiso 1 calc R
C11 C 0.6417(2) 0.9314(3) 0.66441(12) 0.0439(4) Uani 1 d .
H11A H 0.7030(9) 0.9588(5) 0.7123(4) 0.066 Uiso 1 calc R
H11B H 0.5686(2) 1.0128(3) 0.6646(8) 0.066 Uiso 1 calc R
H11C H 0.6802(10) 0.9522(5) 0.6141(4) 0.066 Uiso 1 calc R
C12 C -0.0422(2) 0.7470(3) 0.59513(12) 0.0458(5) Uani 1 d .
H12A H -0.0756(4) 0.6961(14) 0.6433(4) 0.069 Uiso 1 calc R
H12B H -0.0938(3) 0.7046(15) 0.5451(4) 0.069 Uiso 1 calc R
H12C H -0.0438(2) 0.8829(3) 0.5974(8) 0.069 Uiso 1 calc R
Cl Cl 0.33998(4) 1.18028(5) 0.58867(2) 0.0310(2) Uani 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
C2 N1 C10 109.32(11)
C2 N1 C6 111.69(11)
C10 N1 C6 110.80(11)
N1 C2 C3 111.76(11)
C2 C3 C4 111.42(12)
C12 C4 C3 112.08(14)
C12 C4 C5 111.35(13)
C3 C4 C5 108.15(12)
C6 C5 C4 112.51(12)
N1 C6 C7 108.33(11)
N1 C6 C5 109.59(11)
C7 C6 C5 113.44(11)
C6 C7 C8 111.50(12)
C7 C8 C9 111.06(13)
C10 C9 C11 112.85(14)
C10 C9 C8 110.27(13)
C11 C9 C8 112.86(14)
N1 C10 C9 113.75(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.502(2)
N1 C10 1.503(2)
N1 C6 1.514(2)
C2 C3 1.512(2)
C3 C4 1.526(2)
C4 C12 1.524(2)
C4 C5 1.527(2)
C5 C6 1.520(2)
C6 C7 1.517(2)
C7 C8 1.527(2)
C8 C9 1.532(2)
C9 C10 1.518(2)
C9 C11 1.525(2)
