Electronic Supplementary MAterial for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_section_title              
;
Syntheses, crystal structures, and polymorphism of
quaternary pyrrolidinium chlorides
;
_publ_contact_author_name        'Gerhard Laus'
_publ_contact_author_email       Gerhard.Laus@uibk.ac.at
loop_
_publ_author_name
'Gerhard Laus'
'Gino Bentivoglio'
'Volker Kahlenberg'
'Ulrich Griesser'
'Herwig Schottenberger'
;
G.Nauer
;

# Attachment 'LAUS_crystal_data.cif'

data_CCDC617232
_database_code_depnum_ccdc_archive 'CCDC 617232'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H18 N, Cl'
_chemical_formula_sum            'C8 H18 Cl N'
_chemical_formula_weight         163.68

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a b'
_symmetry_space_group_name_Hall  '-P 2bc 2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x-1/2, -y, z'

_cell_length_a                   10.0354(11)
_cell_length_b                   13.254(2)
_cell_length_c                   14.6231(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1945.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9408
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      27.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.373
_exptl_crystal_size_min          0.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13824
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.91
_reflns_number_total             2088
_reflns_number_gt                1666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.7636P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2088
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.44781(4) 0.32505(3) 0.35988(3) 0.03624(13) Uani 1 1 d . . .
N1 N 0.56509(13) 0.13139(10) 0.17048(9) 0.0279(3) Uani 1 1 d . . .
C1 C 0.58020(19) 0.24077(13) 0.14224(13) 0.0368(4) Uani 1 1 d . . .
H1A H 0.6617 0.2501 0.1051 0.044 Uiso 1 1 calc R . .
H1B H 0.5858 0.2849 0.1967 0.044 Uiso 1 1 calc R . .
C2 C 0.61939(18) 0.06431(13) 0.09649(11) 0.0315(4) Uani 1 1 d . . .
H2A H 0.7167 0.0700 0.0949 0.047 Uiso 1 1 calc R . .
H2B H 0.5825 0.0850 0.0373 0.047 Uiso 1 1 calc R . .
H2C H 0.5944 -0.0058 0.1090 0.047 Uiso 1 1 calc R . .
C3 C 0.4568(2) 0.26528(15) 0.08643(15) 0.0484(5) Uani 1 1 d . . .
H3A H 0.4803 0.2736 0.0211 0.058 Uiso 1 1 calc R . .
H3B H 0.4154 0.3286 0.1085 0.058 Uiso 1 1 calc R . .
C4 C 0.63578(17) 0.11388(12) 0.25985(11) 0.0305(4) Uani 1 1 d . . .
H4A H 0.6030 0.1638 0.3050 0.037 Uiso 1 1 calc R . .
H4B H 0.7322 0.1263 0.2508 0.037 Uiso 1 1 calc R . .
C5 C 0.3609(2) 0.17657(16) 0.09866(14) 0.0469(5) Uani 1 1 d . . .
H5A H 0.2696 0.2008 0.1118 0.056 Uiso 1 1 calc R . .
H5B H 0.3587 0.1340 0.0430 0.056 Uiso 1 1 calc R . .
C6 C 0.6873(3) 0.00214(18) 0.39098(14) 0.0564(6) Uani 1 1 d . . .
H6A H 0.7835 0.0106 0.3824 0.085 Uiso 1 1 calc R . .
H6B H 0.6695 -0.0640 0.4184 0.085 Uiso 1 1 calc R . .
H6C H 0.6538 0.0553 0.4314 0.085 Uiso 1 1 calc R . .
C7 C 0.6179(2) 0.00905(14) 0.29939(12) 0.0386(4) Uani 1 1 d . . .
H7A H 0.5218 -0.0056 0.3070 0.046 Uiso 1 1 calc R . .
H7B H 0.6558 -0.0416 0.2570 0.046 Uiso 1 1 calc R . .
C8 C 0.41640(17) 0.11811(15) 0.17924(13) 0.0366(4) Uani 1 1 d . . .
H8A H 0.3836 0.1461 0.2378 0.044 Uiso 1 1 calc R . .
H8B H 0.3915 0.0460 0.1756 0.044 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0344(2) 0.0383(2) 0.0360(2) -0.00566(19) 0.0023(2) 0.00254(18)
N1 0.0275(7) 0.0289(7) 0.0273(7) -0.0021(5) -0.0023(6) 0.0006(6)
C1 0.0434(10) 0.0284(8) 0.0386(9) 0.0009(7) -0.0016(9) 0.0019(7)
C2 0.0348(9) 0.0334(9) 0.0263(8) -0.0033(7) 0.0002(7) 0.0024(7)
C3 0.0582(13) 0.0444(11) 0.0426(11) 0.0006(9) -0.0069(10) 0.0178(10)
C4 0.0326(8) 0.0321(8) 0.0267(8) -0.0039(7) -0.0040(7) -0.0013(7)
C5 0.0369(10) 0.0605(13) 0.0432(11) -0.0111(10) -0.0090(9) 0.0147(9)
C6 0.0816(16) 0.0478(11) 0.0397(10) 0.0067(10) -0.0203(12) -0.0100(11)
C7 0.0464(11) 0.0378(10) 0.0316(9) 0.0018(8) -0.0051(8) -0.0070(8)
C8 0.0257(8) 0.0464(10) 0.0379(9) -0.0065(8) -0.0005(7) -0.0011(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C2 1.503(2) . ?
N1 C4 1.505(2) . ?
N1 C8 1.508(2) . ?
N1 C1 1.515(2) . ?
C1 C3 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C5 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.516(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C8 1.516(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.512(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
C2 N1 C4 111.29(13) . . ?
C2 N1 C8 110.54(13) . . ?
C4 N1 C8 112.00(13) . . ?
C2 N1 C1 109.49(13) . . ?
C4 N1 C1 109.70(13) . . ?
C8 N1 C1 103.53(13) . . ?
N1 C1 C3 105.65(15) . . ?
N1 C1 H1A 110.6 . . ?
C3 C1 H1A 110.6 . . ?
N1 C1 H1B 110.6 . . ?
C3 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C5 106.61(15) . . ?
C1 C3 H3A 110.4 . . ?
C5 C3 H3A 110.4 . . ?
C1 C3 H3B 110.4 . . ?
C5 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
N1 C4 C7 114.65(13) . . ?
N1 C4 H4A 108.6 . . ?
C7 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
C7 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C8 C5 C3 104.61(16) . . ?
C8 C5 H5A 110.8 . . ?
C3 C5 H5A 110.8 . . ?
C8 C5 H5B 110.8 . . ?
C3 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C6 C7 C4 109.82(15) . . ?
C6 C7 H7A 109.7 . . ?
C4 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C4 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C5 103.76(15) . . ?
N1 C8 H8A 111.0 . . ?
C5 C8 H8A 111.0 . . ?
N1 C8 H8B 111.0 . . ?
C5 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.91
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
#===END

data_CCDC617233
_database_code_depnum_ccdc_archive 'CCDC 617233'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 N, Cl'
_chemical_formula_sum            'C8 H16 Cl N'
_chemical_formula_weight         161.67

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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'

_cell_length_a                   6.4857(10)
_cell_length_b                   12.005(3)
_cell_length_c                   12.526(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.746(13)
_cell_angle_gamma                90.00
_cell_volume                     951.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4775
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.23

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7080
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         26.55
_reflns_number_total             1900
_reflns_number_gt                1402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.2336P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1900
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.62337(9) 0.03594(4) 0.77889(4) 0.03035(19) Uani 1 1 d . . .
N1 N 0.8406(3) 0.36494(13) 0.64581(14) 0.0243(4) Uani 1 1 d . . .
C2 C 0.8109(4) 0.47480(18) 0.58797(19) 0.0317(5) Uani 1 1 d . . .
H2A H 0.7706 0.4624 0.5088 0.048 Uiso 1 1 calc R . .
H2B H 0.9433 0.5171 0.6057 0.048 Uiso 1 1 calc R . .
H2C H 0.6993 0.5169 0.6115 0.048 Uiso 1 1 calc R . .
C3 C 0.9104(4) 0.3803(2) 0.76823(17) 0.0318(5) Uani 1 1 d . . .
H3A H 0.7884 0.3982 0.8008 0.038 Uiso 1 1 calc R . .
H3B H 1.0161 0.4408 0.7861 0.038 Uiso 1 1 calc R . .
C4 C 0.6353(4) 0.29921(17) 0.62100(17) 0.0275(5) Uani 1 1 d . . .
H4A H 0.6485 0.2354 0.6721 0.033 Uiso 1 1 calc R . .
H4B H 0.5199 0.3475 0.6344 0.033 Uiso 1 1 calc R . .
C5 C 1.0071(4) 0.2685(2) 0.80979(19) 0.0398(6) Uani 1 1 d . . .
H5A H 0.9023 0.2215 0.8355 0.048 Uiso 1 1 calc R . .
H5B H 1.1312 0.2792 0.8710 0.048 Uiso 1 1 calc R . .
C6 C 0.5427(5) 0.1501(2) 0.4852(2) 0.0424(6) Uani 1 1 d . . .
H6A H 0.5556 0.0985 0.5437 0.051 Uiso 1 1 calc R . .
H6B H 0.5055 0.1248 0.4116 0.051 Uiso 1 1 calc R . .
C7 C 1.0210(4) 0.29983(18) 0.62005(19) 0.0306(5) Uani 1 1 d . . .
H7A H 1.1438 0.3488 0.6200 0.037 Uiso 1 1 calc R . .
H7B H 0.9787 0.2631 0.5478 0.037 Uiso 1 1 calc R . .
C8 C 0.5763(4) 0.25624(19) 0.50592(19) 0.0323(5) Uani 1 1 d . . .
H8 H 0.5629 0.3072 0.4467 0.039 Uiso 1 1 calc R . .
C10 C 1.0734(4) 0.2140(2) 0.7113(2) 0.0411(6) Uani 1 1 d . . .
H10A H 1.2265 0.1969 0.7288 0.049 Uiso 1 1 calc R . .
H10B H 0.9937 0.1442 0.6900 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0306(3) 0.0277(3) 0.0327(3) 0.0020(2) 0.0084(2) -0.0013(2)
N1 0.0233(11) 0.0233(8) 0.0259(8) -0.0005(6) 0.0066(7) -0.0016(7)
C2 0.0338(14) 0.0247(10) 0.0374(12) 0.0035(9) 0.0113(10) -0.0021(9)
C3 0.0344(15) 0.0361(12) 0.0250(10) -0.0026(9) 0.0077(9) -0.0085(9)
C4 0.0228(13) 0.0264(10) 0.0327(11) -0.0004(8) 0.0061(9) -0.0031(8)
C5 0.0370(17) 0.0452(14) 0.0326(12) 0.0098(10) -0.0020(10) -0.0079(11)
C6 0.0482(18) 0.0387(12) 0.0362(13) 0.0045(10) 0.0042(11) 0.0055(11)
C7 0.0253(14) 0.0304(11) 0.0373(12) -0.0003(9) 0.0104(9) 0.0005(9)
C8 0.0298(15) 0.0314(11) 0.0327(11) 0.0021(9) 0.0029(9) -0.0022(9)
C10 0.0311(16) 0.0340(12) 0.0564(15) 0.0108(11) 0.0082(12) 0.0043(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C2 1.497(3) . ?
N1 C7 1.500(3) . ?
N1 C3 1.511(3) . ?
N1 C4 1.520(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C5 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.499(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.539(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.309(3) . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 C10 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C2 N1 C7 112.23(16) . . ?
C2 N1 C3 111.19(16) . . ?
C7 N1 C3 102.05(18) . . ?
C2 N1 C4 110.18(17) . . ?
C7 N1 C4 112.04(16) . . ?
C3 N1 C4 108.87(16) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C5 104.34(18) . . ?
N1 C3 H3A 110.9 . . ?
C5 C3 H3A 110.9 . . ?
N1 C3 H3B 110.9 . . ?
C5 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C8 C4 N1 113.68(18) . . ?
C8 C4 H4A 108.8 . . ?
N1 C4 H4A 108.8 . . ?
C8 C4 H4B 108.8 . . ?
N1 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C3 C5 C10 105.49(18) . . ?
C3 C5 H5A 110.6 . . ?
C10 C5 H5A 110.6 . . ?
C3 C5 H5B 110.6 . . ?
C10 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
C8 C6 H6A 120.0 . . ?
C8 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N1 C7 C10 104.29(17) . . ?
N1 C7 H7A 110.9 . . ?
C10 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C10 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C6 C8 C4 121.5(2) . . ?
C6 C8 H8 119.3 . . ?
C4 C8 H8 119.3 . . ?
C7 C10 C5 105.02(19) . . ?
C7 C10 H10A 110.7 . . ?
C5 C10 H10A 110.7 . . ?
C7 C10 H10B 110.7 . . ?
C5 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.55
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050
#===END

data_CCDC644230
_database_code_depnum_ccdc_archive 'CCDC 644230'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N, Cl'
_chemical_formula_sum            'C8 H14 Cl N'
_chemical_formula_weight         159.65

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

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'

_cell_length_a                   8.4849(14)
_cell_length_b                   8.1271(16)
_cell_length_c                   13.501(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.408(13)
_cell_angle_gamma                90.00
_cell_volume                     915.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1918
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.61

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5415
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         24.61
_reflns_number_total             1457
_reflns_number_gt                1333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1457
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.44073(4) 0.69729(4) 0.15955(3) 0.02870(14) Uani 1 1 d . . .
N1 N 0.48691(14) 0.22530(14) 0.26488(9) 0.0238(3) Uani 1 1 d . . .
C5 C 0.35914(17) 0.24850(19) 0.17212(12) 0.0289(3) Uani 1 1 d . . .
H5A H 0.3477 0.3662 0.1533 0.035 Uiso 1 1 calc R . .
H5B H 0.2544 0.2067 0.1838 0.035 Uiso 1 1 calc R . .
C4 C 0.4184(2) 0.1488(2) 0.08992(12) 0.0351(4) Uani 1 1 d . . .
H4A H 0.3976 0.2086 0.0250 0.042 Uiso 1 1 calc R . .
H4B H 0.3640 0.0406 0.0809 0.042 Uiso 1 1 calc R . .
C3 C 0.5998(2) 0.1267(2) 0.12694(13) 0.0354(4) Uani 1 1 d . . .
H3A H 0.6260 0.0097 0.1422 0.043 Uiso 1 1 calc R . .
H3B H 0.6608 0.1650 0.0754 0.043 Uiso 1 1 calc R . .
C2 C 0.63888(17) 0.23081(19) 0.22147(12) 0.0305(4) Uani 1 1 d . . .
H2A H 0.7302 0.1838 0.2692 0.037 Uiso 1 1 calc R . .
H2B H 0.6653 0.3451 0.2050 0.037 Uiso 1 1 calc R . .
C1 C 0.4818(2) 0.35774(19) 0.34087(12) 0.0331(4) Uani 1 1 d . . .
H1A H 0.4924 0.4653 0.3099 0.050 Uiso 1 1 calc R . .
H1B H 0.5700 0.3422 0.3978 0.050 Uiso 1 1 calc R . .
H1C H 0.3794 0.3527 0.3647 0.050 Uiso 1 1 calc R . .
C6 C 0.46329(16) 0.05928(17) 0.31069(11) 0.0255(3) Uani 1 1 d . . .
H6A H 0.3627 0.0608 0.3382 0.031 Uiso 1 1 calc R . .
H6B H 0.4525 -0.0259 0.2575 0.031 Uiso 1 1 calc R . .
C7 C 0.59655(18) 0.01611(18) 0.39104(13) 0.0288(3) Uani 1 1 d . . .
C8 C 0.7052(2) -0.0230(2) 0.45427(13) 0.0360(4) Uani 1 1 d . . .
H8 H 0.7926 -0.0544 0.5051 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0273(2) 0.0246(2) 0.0338(2) -0.00234(14) 0.00457(15) -0.00358(13)
N1 0.0239(6) 0.0202(6) 0.0275(7) 0.0005(5) 0.0054(5) -0.0003(5)
C5 0.0274(8) 0.0260(7) 0.0313(9) 0.0031(6) -0.0001(6) 0.0018(6)
C4 0.0459(9) 0.0301(8) 0.0285(9) 0.0007(6) 0.0048(7) 0.0007(7)
C3 0.0429(9) 0.0285(8) 0.0394(10) 0.0021(7) 0.0195(7) 0.0004(7)
C2 0.0260(8) 0.0287(8) 0.0395(10) 0.0038(6) 0.0126(7) -0.0036(6)
C1 0.0409(9) 0.0250(8) 0.0335(10) -0.0054(6) 0.0072(7) 0.0003(7)
C6 0.0264(7) 0.0215(7) 0.0297(9) 0.0027(6) 0.0079(6) -0.0016(6)
C7 0.0339(8) 0.0246(8) 0.0304(9) 0.0009(6) 0.0124(7) 0.0033(6)
C8 0.0414(9) 0.0361(9) 0.0305(10) 0.0004(7) 0.0068(7) 0.0103(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C1 1.4930(19) . ?
N1 C2 1.5104(19) . ?
N1 C6 1.5127(18) . ?
N1 C5 1.5128(19) . ?
C5 C4 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 C3 1.540(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C2 1.517(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C6 C7 1.461(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.181(2) . ?
C8 H8 0.9500 . ?

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 N1 C2 112.23(11) . . ?
C1 N1 C6 109.85(12) . . ?
C2 N1 C6 111.75(11) . . ?
C1 N1 C5 111.93(11) . . ?
C2 N1 C5 102.09(12) . . ?
C6 N1 C5 108.76(11) . . ?
N1 C5 C4 104.71(12) . . ?
N1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C5 C4 C3 105.45(13) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C2 C3 C4 105.18(12) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C2 C3 103.74(12) . . ?
N1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
N1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 N1 112.07(11) . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
N1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 177.93(17) . . ?
C7 C8 H8 180.0 . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        24.61
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033
#===END


