# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Edward Tiekink'
_publ_contact_author_email       EDWARD.TIEKINK@UTSA.EDU

_publ_section_title              
;
Assessing the persistence of the N-H...N hydrogen
bonding leading to supramolecular chains in molecules related to the
anti-malarial drug, chloroquine
;
loop_
_publ_author_name
'Edward R.T. Tiekink'
'Marcus Vinicius De Souza'
'Carlos R. Kaiser'
'Karla C. Pais'
'J Wardell'
;
S.M.S.V.Wardell
;

# Attachment '1_Me.CIF'

data_Me
_database_code_depnum_ccdc_archive 'CCDC 697891'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Cl N2'
_chemical_formula_sum            'C10 H9 Cl N2'
_chemical_formula_weight         192.64

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   4.6812(9)
_cell_length_b                   14.097(4)
_cell_length_c                   13.296(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.967(7)
_cell_angle_gamma                90
_cell_volume                     864.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    699
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      30.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            8722
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.1
_diffrn_reflns_theta_max         26.5
_reflns_number_total             1790
_reflns_number_gt                1756
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0422P)²+0.4506P] where P=(Fo²+2Fc²)/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         1790
_refine_ls_number_parameters     122
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.030
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.080
_refine_ls_wR_factor_gt          0.079
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          <0.001
_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 -0.26339(7) 0.00704(2) 0.16963(2) 0.01912(12) Uani 1 1 d . . .
N1 N 0.4746(2) 0.26600(8) 0.27981(8) 0.0168(2) Uani 1 1 d . . .
N2 N 0.5480(2) 0.33684(8) -0.02331(8) 0.0160(2) Uani 1 1 d D . .
H2N H 0.4955 0.2958 -0.0729 0.019 Uiso 1 1 d D . .
C1 C 0.6483(3) 0.33382(9) 0.25677(9) 0.0172(3) Uani 1 1 d . . .
H1 H 0.7596 0.3672 0.3122 0.021 Uiso 1 1 calc R . .
C2 C 0.6826(3) 0.36077(9) 0.15840(9) 0.0166(3) Uani 1 1 d . . .
H2 H 0.8106 0.4110 0.1491 0.020 Uiso 1 1 calc R . .
C3 C 0.5285(3) 0.31360(8) 0.07426(9) 0.0141(3) Uani 1 1 d . . .
C4 C 0.3342(3) 0.23931(8) 0.09471(9) 0.0138(2) Uani 1 1 d . . .
C5 C 0.1584(3) 0.18721(9) 0.01650(9) 0.0160(3) Uani 1 1 d . . .
H5 H 0.1684 0.2005 -0.0529 0.019 Uiso 1 1 calc R . .
C6 C -0.0266(3) 0.11784(9) 0.03904(9) 0.0169(3) Uani 1 1 d . . .
H6 H -0.1461 0.0839 -0.0140 0.020 Uiso 1 1 calc R . .
C7 C -0.0360(3) 0.09789(9) 0.14211(10) 0.0159(3) Uani 1 1 d . . .
C8 C 0.1290(3) 0.14623(9) 0.22017(9) 0.0161(3) Uani 1 1 d . . .
H8 H 0.1177 0.1312 0.2890 0.019 Uiso 1 1 calc R . .
C9 C 0.3172(3) 0.21895(9) 0.19809(9) 0.0147(3) Uani 1 1 d . . .
C10 C 0.7517(3) 0.40802(9) -0.04607(10) 0.0181(3) Uani 1 1 d . . .
H10A H 0.7147 0.4681 -0.0136 0.027 Uiso 1 1 calc R . .
H10B H 0.7277 0.4170 -0.1202 0.027 Uiso 1 1 calc R . .
H10C H 0.9501 0.3870 -0.0198 0.027 Uiso 1 1 calc R . .


_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
Cl1 C7 1.7443(13) . ?
N1 C1 1.3249(17) . ?
N1 C9 1.3734(16) . ?
N2 C3 1.3564(16) . ?
N2 C10 1.4515(16) . ?
N2 H2N 0.8799 . ?
C1 C2 1.3977(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3910(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4433(17) . ?
C4 C5 1.4150(17) . ?
C4 C9 1.4198(17) . ?
C5 C6 1.3731(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4071(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3640(18) . ?
C8 C9 1.4152(18) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 C9 115.61(11) . . ?
C3 N2 C10 121.45(10) . . ?
C3 N2 H2N 120.2 . . ?
C10 N2 H2N 114.0 . . ?
N1 C1 C2 125.96(12) . . ?
N1 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C3 C2 C1 119.66(12) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N2 C3 C2 122.84(12) . . ?
N2 C3 C4 120.29(11) . . ?
C2 C3 C4 116.84(11) . . ?
C5 C4 C9 118.91(11) . . ?
C5 C4 C3 122.94(11) . . ?
C9 C4 C3 118.15(11) . . ?
C6 C5 C4 121.19(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.82(11) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 122.15(12) . . ?
C8 C7 Cl1 119.54(10) . . ?
C6 C7 Cl1 118.30(10) . . ?
C7 C8 C9 119.66(11) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C8 116.98(11) . . ?
N1 C9 C4 123.78(11) . . ?
C8 C9 C4 119.25(11) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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 N1 C1 C2 0.17(18) . . . . ?
N1 C1 C2 C3 -0.9(2) . . . . ?
C10 N2 C3 C2 5.26(18) . . . . ?
C10 N2 C3 C4 -176.96(10) . . . . ?
C1 C2 C3 N2 179.04(11) . . . . ?
C1 C2 C3 C4 1.19(17) . . . . ?
N2 C3 C4 C5 0.37(18) . . . . ?
C2 C3 C4 C5 178.28(12) . . . . ?
N2 C3 C4 C9 -178.73(11) . . . . ?
C2 C3 C4 C9 -0.83(17) . . . . ?
C9 C4 C5 C6 -0.05(18) . . . . ?
C3 C4 C5 C6 -179.15(11) . . . . ?
C4 C5 C6 C7 -1.00(18) . . . . ?
C5 C6 C7 C8 1.09(19) . . . . ?
C5 C6 C7 Cl1 -177.99(9) . . . . ?
C6 C7 C8 C9 -0.08(19) . . . . ?
Cl1 C7 C8 C9 178.99(9) . . . . ?
C1 N1 C9 C8 -179.85(11) . . . . ?
C1 N1 C9 C4 0.22(17) . . . . ?
C7 C8 C9 N1 179.07(11) . . . . ?
C7 C8 C9 C4 -0.99(18) . . . . ?
C5 C4 C9 N1 -179.01(11) . . . . ?
C3 C4 C9 N1 0.13(18) . . . . ?
C5 C4 C9 C8 1.05(17) . . . . ?
C3 C4 C9 C8 -179.80(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.048

# Attachment '2_nPr.CIF'

data_nPr
_database_code_depnum_ccdc_archive 'CCDC 697892'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 Cl N2'
_chemical_formula_sum            'C12 H13 Cl N2'
_chemical_formula_weight         220.69

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   10.4386(3)
_cell_length_b                   17.9769(5)
_cell_length_c                   13.0512(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.987(2)
_cell_angle_gamma                90
_cell_volume                     2315.85(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5401
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       rod
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33628
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             5297
_reflns_number_gt                3930
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.1031P)²+1.6308P] where P=(Fo²+2Fc²)/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         5297
_refine_ls_number_parameters     277
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.086
_refine_ls_R_factor_gt           0.059
_refine_ls_wR_factor_ref         0.189
_refine_ls_wR_factor_gt          0.165
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          <0.001
_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 0.92021(7) 0.46245(4) 0.60977(6) 0.0384(2) Uani 1 1 d . . .
Cl1A Cl 0.76025(7) 0.01571(4) 0.63660(7) 0.0425(2) Uani 1 1 d . . .
N1 N 0.6077(2) 0.25218(13) 0.42238(15) 0.0267(5) Uani 1 1 d . . .
N2 N 0.5607(2) 0.17474(11) 0.71318(16) 0.0235(4) Uani 1 1 d D . .
H2N H 0.5872 0.2016 0.7727 0.028 Uiso 1 1 d D . .
N1A N 1.0547(2) 0.22809(12) 0.84096(15) 0.0267(5) Uani 1 1 d . . .
N2A N 1.1180(2) 0.31452(12) 0.56132(16) 0.0266(5) Uani 1 1 d D . .
H2NA H 1.0810 0.2949 0.4967 0.032 Uiso 1 1 d D . .
C1 C 0.5346(3) 0.19270(15) 0.42721(19) 0.0279(6) Uani 1 1 d . . .
H1 H 0.4924 0.1670 0.3612 0.033 Uiso 1 1 calc R . .
C2 C 0.5137(2) 0.16440(14) 0.51944(19) 0.0256(5) Uani 1 1 d . . .
H2 H 0.4587 0.1216 0.5148 0.031 Uiso 1 1 calc R . .
C3 C 0.5743(2) 0.19934(13) 0.61914(17) 0.0196(5) Uani 1 1 d . . .
C4 C 0.6569(2) 0.26374(13) 0.61910(17) 0.0183(5) Uani 1 1 d . . .
C5 C 0.7278(2) 0.30324(13) 0.71453(18) 0.0202(5) Uani 1 1 d . . .
H5 H 0.7202 0.2877 0.7819 0.024 Uiso 1 1 calc R . .
C6 C 0.8073(2) 0.36364(13) 0.71175(19) 0.0241(5) Uani 1 1 d . . .
H6 H 0.8544 0.3896 0.7764 0.029 Uiso 1 1 calc R . .
C7 C 0.8180(2) 0.38641(13) 0.6117(2) 0.0244(5) Uani 1 1 d . . .
C8 C 0.7514(2) 0.35017(14) 0.5177(2) 0.0252(5) Uani 1 1 d . . .
H8 H 0.7597 0.3669 0.4511 0.030 Uiso 1 1 calc R . .
C9 C 0.6698(2) 0.28768(13) 0.51911(18) 0.0207(5) Uani 1 1 d . . .
C10 C 0.4800(2) 0.11040(14) 0.7210(2) 0.0258(5) Uani 1 1 d . . .
H10A H 0.5136 0.0912 0.7962 0.031 Uiso 1 1 calc R . .
H10B H 0.4937 0.0709 0.6728 0.031 Uiso 1 1 calc R . .
C11 C 0.3288(3) 0.12589(15) 0.6912(2) 0.0307(6) Uani 1 1 d . . .
H11A H 0.3134 0.1635 0.7414 0.037 Uiso 1 1 calc R . .
H11B H 0.2944 0.1464 0.6168 0.037 Uiso 1 1 calc R . .
C12 C 0.2515(3) 0.05510(17) 0.6974(3) 0.0428(7) Uani 1 1 d . . .
H12A H 0.1544 0.0661 0.6761 0.064 Uiso 1 1 calc R . .
H12B H 0.2829 0.0360 0.7718 0.064 Uiso 1 1 calc R . .
H12C H 0.2676 0.0177 0.6484 0.064 Uiso 1 1 calc R . .
C1A C 1.1331(3) 0.28631(15) 0.84294(19) 0.0274(5) Uani 1 1 d . . .
H1A H 1.1748 0.3093 0.9113 0.033 Uiso 1 1 calc R . .
C2A C 1.1602(2) 0.31701(14) 0.75402(18) 0.0236(5) Uani 1 1 d . . .
H2A H 1.2191 0.3586 0.7632 0.028 Uiso 1 1 calc R . .
C3A C 1.0998(2) 0.28609(13) 0.65108(17) 0.0194(5) Uani 1 1 d . . .
C4A C 1.0152(2) 0.22172(13) 0.64481(17) 0.0185(5) Uani 1 1 d . . .
C5A C 0.9495(2) 0.18378(13) 0.54661(18) 0.0223(5) Uani 1 1 d . . .
H5A H 0.9592 0.2017 0.4811 0.027 Uiso 1 1 calc R . .
C6A C 0.8719(3) 0.12146(14) 0.5441(2) 0.0268(5) Uani 1 1 d . . .
H6A H 0.8289 0.0964 0.4777 0.032 Uiso 1 1 calc R . .
C7A C 0.8574(2) 0.09563(13) 0.6412(2) 0.0269(5) Uani 1 1 d . . .
C8A C 0.9163(2) 0.13082(14) 0.7375(2) 0.0256(5) Uani 1 1 d . . .
H8A H 0.9035 0.1124 0.8017 0.031 Uiso 1 1 calc R . .
C9A C 0.9968(2) 0.19528(13) 0.74170(18) 0.0214(5) Uani 1 1 d . . .
C10A C 1.2039(3) 0.37756(15) 0.5600(2) 0.0346(6) Uani 1 1 d . . .
H10C H 1.1980 0.4138 0.6154 0.041 Uiso 1 1 calc R . .
H10D H 1.1689 0.4022 0.4885 0.041 Uiso 1 1 calc R . .
C11A C 1.3482(3) 0.35800(16) 0.5811(2) 0.0368(6) Uani 1 1 d . . .
H11C H 1.3554 0.3215 0.5264 0.044 Uiso 1 1 calc R . .
H11D H 1.3851 0.3347 0.6535 0.044 Uiso 1 1 calc R . .
C12A C 1.4311(3) 0.42739(18) 0.5763(4) 0.0636(11) Uani 1 1 d . . .
H12D H 1.5263 0.4135 0.5917 0.095 Uiso 1 1 calc R . .
H12E H 1.4238 0.4635 0.6303 0.095 Uiso 1 1 calc R . .
H12F H 1.3964 0.4495 0.5039 0.095 Uiso 1 1 calc R . .


_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
Cl1 C7 1.739(2) . ?
Cl1A C7A 1.748(2) . ?
N1 C1 1.327(3) . ?
N1 C9 1.374(3) . ?
N2 C3 1.355(3) . ?
N2 C10 1.453(3) . ?
N2 H2N 0.8800 . ?
N1A C1A 1.324(3) . ?
N1A C9A 1.372(3) . ?
N2A C3A 1.347(3) . ?
N2A C10A 1.448(3) . ?
N2A H2NA 0.8800 . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.443(3) . ?
C4 C5 1.415(3) . ?
C4 C9 1.422(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(4) . ?
C8 C9 1.413(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1A C2A 1.394(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.400(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.442(3) . ?
C4A C5A 1.416(3) . ?
C4A C9A 1.421(3) . ?
C5A C6A 1.376(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.403(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.362(4) . ?
C8A C9A 1.422(3) . ?
C8A H8A 0.9500 . ?
C10A C11A 1.483(4) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.531(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

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 C9 115.92(19) . . ?
C3 N2 C10 123.9(2) . . ?
C3 N2 H2N 121.7 . . ?
C10 N2 H2N 113.4 . . ?
C1A N1A C9A 115.97(19) . . ?
C3A N2A C10A 124.8(2) . . ?
C3A N2A H2NA 122.6 . . ?
C10A N2A H2NA 112.6 . . ?
N1 C1 C2 126.3(2) . . ?
N1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C3 C2 123.2(2) . . ?
N2 C3 C4 120.1(2) . . ?
C2 C3 C4 116.7(2) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 122.91(19) . . ?
C9 C4 C3 118.6(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 Cl1 119.90(18) . . ?
C6 C7 Cl1 118.42(19) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
N1 C9 C8 117.6(2) . . ?
N1 C9 C4 123.0(2) . . ?
C8 C9 C4 119.4(2) . . ?
N2 C10 C11 114.3(2) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 110.9(2) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1A C1A C2A 126.0(2) . . ?
N1A C1A H1A 117.0 . . ?
C2A C1A H1A 117.0 . . ?
C1A C2A C3A 119.4(2) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
N2A C3A C2A 122.5(2) . . ?
N2A C3A C4A 120.8(2) . . ?
C2A C3A C4A 116.7(2) . . ?
C5A C4A C9A 118.6(2) . . ?
C5A C4A C3A 123.03(19) . . ?
C9A C4A C3A 118.4(2) . . ?
C6A C5A C4A 121.4(2) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C7A 118.9(2) . . ?
C5A C6A H6A 120.5 . . ?
C7A C6A H6A 120.5 . . ?
C8A C7A C6A 122.1(2) . . ?
C8A C7A Cl1A 119.71(19) . . ?
C6A C7A Cl1A 118.2(2) . . ?
C7A C8A C9A 119.8(2) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A H8A 120.1 . . ?
N1A C9A C4A 123.4(2) . . ?
N1A C9A C8A 117.4(2) . . ?
C4A C9A C8A 119.2(2) . . ?
N2A C10A C11A 114.0(2) . . ?
N2A C10A H10C 108.7 . . ?
C11A C10A H10C 108.7 . . ?
N2A C10A H10D 108.7 . . ?
C11A C10A H10D 108.7 . . ?
H10C C10A H10D 107.6 . . ?
C10A C11A C12A 110.7(2) . . ?
C10A C11A H11C 109.5 . . ?
C12A C11A H11C 109.5 . . ?
C10A C11A H11D 109.5 . . ?
C12A C11A H11D 109.5 . . ?
H11C C11A H11D 108.1 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

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 N1 C1 C2 1.1(4) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C10 N2 C3 C2 -1.1(4) . . . . ?
C10 N2 C3 C4 -179.8(2) . . . . ?
C1 C2 C3 N2 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
N2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C5 -178.0(2) . . . . ?
N2 C3 C4 C9 179.5(2) . . . . ?
C2 C3 C4 C9 0.7(3) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 Cl1 -179.47(18) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
Cl1 C7 C8 C9 179.05(17) . . . . ?
C1 N1 C9 C8 178.5(2) . . . . ?
C1 N1 C9 C4 -0.7(3) . . . . ?
C7 C8 C9 N1 -178.4(2) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C5 C4 C9 N1 178.5(2) . . . . ?
C3 C4 C9 N1 -0.2(3) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 -179.4(2) . . . . ?
C3 N2 C10 C11 -81.3(3) . . . . ?
N2 C10 C11 C12 177.8(2) . . . . ?
C9A N1A C1A C2A 0.7(4) . . . . ?
N1A C1A C2A C3A 1.0(4) . . . . ?
C10A N2A C3A C2A 2.1(4) . . . . ?
C10A N2A C3A C4A -178.2(2) . . . . ?
C1A C2A C3A N2A 177.8(2) . . . . ?
C1A C2A C3A C4A -1.9(3) . . . . ?
N2A C3A C4A C5A 1.5(3) . . . . ?
C2A C3A C4A C5A -178.8(2) . . . . ?
N2A C3A C4A C9A -178.4(2) . . . . ?
C2A C3A C4A C9A 1.2(3) . . . . ?
C9A C4A C5A C6A -1.6(3) . . . . ?
C3A C4A C5A C6A 178.5(2) . . . . ?
C4A C5A C6A C7A 0.4(4) . . . . ?
C5A C6A C7A C8A 0.8(4) . . . . ?
C5A C6A C7A Cl1A -179.20(19) . . . . ?
C6A C7A C8A C9A -0.9(4) . . . . ?
Cl1A C7A C8A C9A 179.17(18) . . . . ?
C1A N1A C9A C4A -1.4(3) . . . . ?
C1A N1A C9A C8A 177.6(2) . . . . ?
C5A C4A C9A N1A -179.5(2) . . . . ?
C3A C4A C9A N1A 0.4(3) . . . . ?
C5A C4A C9A C8A 1.5(3) . . . . ?
C3A C4A C9A C8A -178.6(2) . . . . ?
C7A C8A C9A N1A -179.4(2) . . . . ?
C7A C8A C9A C4A -0.3(3) . . . . ?
C3A N2A C10A C11A 85.4(3) . . . . ?
N2A C10A C11A C12A 179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.31
# 1.02 A from atom H11c
_refine_diff_density_min         -0.50
# 0.70 A from atom C11a
_refine_diff_density_rms         0.164

# Attachment '3_nBu.CIF'

data_nBu
_database_code_depnum_ccdc_archive 'CCDC 697893'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Cl N2'
_chemical_formula_sum            'C13 H15 Cl N2'
_chemical_formula_weight         234.72

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

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

_cell_length_a                   9.3167(3)
_cell_length_b                   20.4346(11)
_cell_length_c                   25.3335(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4823.1(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5750
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31816
_diffrn_reflns_av_R_equivalents  0.097
_diffrn_reflns_av_sigmaI/netI    0.082
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             5448
_reflns_number_gt                3365
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0781P)²] where P=(Fo²+2Fc²)/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         5448
_refine_ls_number_parameters     295
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.110
_refine_ls_R_factor_gt           0.055
_refine_ls_wR_factor_ref         0.156
_refine_ls_wR_factor_gt          0.128
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          <0.001
_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 0.98938(7) -0.18702(3) 0.77435(3) 0.0307(2) Uani 1 1 d . . .
Cl1A Cl 0.48122(7) -0.17364(3) 0.54392(3) 0.0326(2) Uani 1 1 d . . .
N1 N 0.6452(2) -0.03163(10) 0.86693(8) 0.0239(5) Uani 1 1 d . . .
N2 N 0.5363(2) 0.06703(11) 0.72614(9) 0.0227(5) Uani 1 1 d D . .
H2N H 0.5660 0.0505 0.6960 0.027 Uiso 1 1 d D . .
N1A N 0.6538(2) 0.04462(11) 0.61510(9) 0.0240(5) Uani 1 1 d . . .
N2A N 0.8688(2) 0.09558(10) 0.47411(9) 0.0239(5) Uani 1 1 d D . .
H2NA H 0.8549 0.0736 0.4447 0.029 Uiso 1 1 d D . .
C1 C 0.5576(3) 0.01927(13) 0.86513(10) 0.0244(6) Uani 1 1 d . . .
H1 H 0.5157 0.0329 0.8975 0.029 Uiso 1 1 calc R . .
C2 C 0.5211(2) 0.05460(13) 0.82036(10) 0.0227(6) Uani 1 1 d . . .
H2 H 0.4598 0.0916 0.8232 0.027 Uiso 1 1 calc R . .
C3 C 0.5743(3) 0.03592(12) 0.77137(10) 0.0190(6) Uani 1 1 d . . .
C4 C 0.6742(2) -0.01822(12) 0.77096(10) 0.0199(6) Uani 1 1 d . . .
C5 C 0.7443(2) -0.03995(12) 0.72459(10) 0.0203(6) Uani 1 1 d . . .
H5 H 0.7244 -0.0189 0.6920 0.024 Uiso 1 1 calc R . .
C6 C 0.8401(3) -0.09070(12) 0.72587(11) 0.0230(6) Uani 1 1 d . . .
H6 H 0.8880 -0.1042 0.6946 0.028 Uiso 1 1 calc R . .
C7 C 0.8668(2) -0.12240(12) 0.77392(11) 0.0226(6) Uani 1 1 d . . .
C8 C 0.8011(3) -0.10355(12) 0.81983(11) 0.0229(6) Uani 1 1 d . . .
H8 H 0.8200 -0.1264 0.8517 0.027 Uiso 1 1 calc R . .
C9 C 0.7051(2) -0.04996(12) 0.81956(10) 0.0205(6) Uani 1 1 d . . .
C10 C 0.4301(3) 0.11959(12) 0.72627(10) 0.0231(6) Uani 1 1 d . . .
H10A H 0.4723 0.1588 0.7431 0.028 Uiso 1 1 calc R . .
H10B H 0.3463 0.1059 0.7476 0.028 Uiso 1 1 calc R . .
C11 C 0.3798(3) 0.13720(13) 0.67114(10) 0.0245(6) Uani 1 1 d . . .
H11A H 0.3381 0.0980 0.6540 0.029 Uiso 1 1 calc R . .
H11B H 0.4628 0.1518 0.6498 0.029 Uiso 1 1 calc R . .
C12 C 0.2677(3) 0.19149(13) 0.67295(11) 0.0286(7) Uani 1 1 d . . .
H12A H 0.1903 0.1787 0.6976 0.034 Uiso 1 1 calc R . .
H12B H 0.3129 0.2318 0.6869 0.034 Uiso 1 1 calc R . .
C13 C 0.2023(3) 0.20610(15) 0.61923(12) 0.0384(8) Uani 1 1 d . . .
H13A H 0.1310 0.2411 0.6228 0.058 Uiso 1 1 calc R . .
H13B H 0.1558 0.1666 0.6055 0.058 Uiso 1 1 calc R . .
H13C H 0.2779 0.2200 0.5948 0.058 Uiso 1 1 calc R . .
C1A C 0.7231(3) 0.10060(13) 0.60808(11) 0.0246(6) Uani 1 1 d . . .
H1A H 0.7233 0.1303 0.6369 0.029 Uiso 1 1 calc R . .
C2A C 0.7956(3) 0.12029(13) 0.56281(10) 0.0226(6) Uani 1 1 d . . .
H2A H 0.8435 0.1613 0.5618 0.027 Uiso 1 1 calc R . .
C3A C 0.7973(3) 0.07891(13) 0.51872(10) 0.0214(6) Uani 1 1 d . . .
C4A C 0.7216(2) 0.01780(13) 0.52357(10) 0.0209(6) Uani 1 1 d . . .
C5A C 0.7104(3) -0.02829(13) 0.48192(11) 0.0252(6) Uani 1 1 d . . .
H5A H 0.7542 -0.0189 0.4489 0.030 Uiso 1 1 calc R . .
C6A C 0.6381(3) -0.08576(13) 0.48816(11) 0.0284(6) Uani 1 1 d . . .
H6A H 0.6307 -0.1159 0.4597 0.034 Uiso 1 1 calc R . .
C7A C 0.5747(3) -0.09995(13) 0.53714(11) 0.0248(6) Uani 1 1 d . . .
C8A C 0.5822(3) -0.05743(13) 0.57846(11) 0.0253(6) Uani 1 1 d . . .
H8A H 0.5387 -0.0683 0.6112 0.030 Uiso 1 1 calc R . .
C9A C 0.6548(2) 0.00279(12) 0.57247(11) 0.0222(6) Uani 1 1 d . . .
C10A C 0.9516(3) 0.15597(13) 0.47050(11) 0.0256(6) Uani 1 1 d . . .
H10C H 1.0192 0.1584 0.5006 0.031 Uiso 1 1 calc R . .
H10D H 0.8858 0.1939 0.4728 0.031 Uiso 1 1 calc R . .
C11A C 1.0355(3) 0.15952(13) 0.41896(11) 0.0251(6) Uani 1 1 d . . .
H11C H 1.0932 0.1192 0.4148 0.030 Uiso 1 1 calc R . .
H11D H 0.9674 0.1620 0.3890 0.030 Uiso 1 1 calc R . .
C12A C 1.1344(3) 0.21879(13) 0.41763(11) 0.0279(6) Uani 1 1 d . . .
H12C H 1.0761 0.2591 0.4208 0.033 Uiso 1 1 calc R . .
H12D H 1.2001 0.2170 0.4483 0.033 Uiso 1 1 calc R . .
C13A C 1.2226(3) 0.22211(14) 0.36712(11) 0.0323(7) Uani 1 1 d . . .
H13D H 1.2839 0.2611 0.3679 0.048 Uiso 1 1 calc R . .
H13E H 1.1581 0.2245 0.3366 0.048 Uiso 1 1 calc R . .
H13F H 1.2827 0.1829 0.3643 0.048 Uiso 1 1 calc R . .


_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
Cl1 C7 1.746(2) . ?
Cl1A C7A 1.748(3) . ?
N1 C1 1.323(3) . ?
N1 C9 1.375(3) . ?
N2 C3 1.357(3) . ?
N2 C10 1.460(3) . ?
N2 H2N 0.8800 . ?
N1A C1A 1.326(3) . ?
N1A C9A 1.377(3) . ?
N2A C3A 1.355(3) . ?
N2A C10A 1.458(3) . ?
N2A H2NA 0.8800 . ?
C1 C2 1.387(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.446(3) . ?
C4 C5 1.415(3) . ?
C4 C9 1.421(3) . ?
C5 C6 1.369(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(4) . ?
C8 C9 1.414(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C1A C2A 1.390(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.401(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.440(4) . ?
C4A C5A 1.418(4) . ?
C4A C9A 1.420(3) . ?
C5A C6A 1.363(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.405(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.362(4) . ?
C8A C9A 1.412(3) . ?
C8A H8A 0.9500 . ?
C10A C11A 1.523(4) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.523(3) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.522(4) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?

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 C9 115.8(2) . . ?
C3 N2 C10 121.3(2) . . ?
C3 N2 H2N 118.0 . . ?
C10 N2 H2N 119.9 . . ?
C1A N1A C9A 115.3(2) . . ?
C3A N2A C10A 121.7(2) . . ?
C3A N2A H2NA 120.4 . . ?
C10A N2A H2NA 117.1 . . ?
N1 C1 C2 126.0(2) . . ?
N1 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C3 C2 122.2(2) . . ?
N2 C3 C4 121.3(2) . . ?
C2 C3 C4 116.5(2) . . ?
C5 C4 C9 118.8(2) . . ?
C5 C4 C3 122.9(2) . . ?
C9 C4 C3 118.3(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.1(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 Cl1 120.0(2) . . ?
C6 C7 Cl1 118.1(2) . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C8 117.6(2) . . ?
N1 C9 C4 123.3(2) . . ?
C8 C9 C4 119.1(2) . . ?
N2 C10 C11 112.4(2) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 110.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 113.0(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1A C1A C2A 126.6(3) . . ?
N1A C1A H1A 116.7 . . ?
C2A C1A H1A 116.7 . . ?
C1A C2A C3A 119.2(2) . . ?
C1A C2A H2A 120.4 . . ?
C3A C2A H2A 120.4 . . ?
N2A C3A C2A 121.2(2) . . ?
N2A C3A C4A 122.0(2) . . ?
C2A C3A C4A 116.7(2) . . ?
C5A C4A C9A 118.3(2) . . ?
C5A C4A C3A 123.3(2) . . ?
C9A C4A C3A 118.5(2) . . ?
C6A C5A C4A 121.5(2) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C7A 119.2(3) . . ?
C5A C6A H6A 120.4 . . ?
C7A C6A H6A 120.4 . . ?
C8A C7A C6A 121.7(2) . . ?
C8A C7A Cl1A 120.0(2) . . ?
C6A C7A Cl1A 118.3(2) . . ?
C7A C8A C9A 119.9(2) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A H8A 120.1 . . ?
N1A C9A C8A 117.0(2) . . ?
N1A C9A C4A 123.6(2) . . ?
C8A C9A C4A 119.5(2) . . ?
N2A C10A C11A 111.4(2) . . ?
N2A C10A H10C 109.3 . . ?
C11A C10A H10C 109.3 . . ?
N2A C10A H10D 109.3 . . ?
C11A C10A H10D 109.3 . . ?
H10C C10A H10D 108.0 . . ?
C12A C11A C10A 111.6(2) . . ?
C12A C11A H11C 109.3 . . ?
C10A C11A H11C 109.3 . . ?
C12A C11A H11D 109.3 . . ?
C10A C11A H11D 109.3 . . ?
H11C C11A H11D 108.0 . . ?
C13A C12A C11A 112.4(2) . . ?
C13A C12A H12C 109.1 . . ?
C11A C12A H12C 109.1 . . ?
C13A C12A H12D 109.1 . . ?
C11A C12A H12D 109.1 . . ?
H12C C12A H12D 107.9 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

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 N1 C1 C2 0.4(4) . . . . ?
N1 C1 C2 C3 2.4(4) . . . . ?
C10 N2 C3 C2 -3.8(4) . . . . ?
C10 N2 C3 C4 177.0(2) . . . . ?
C1 C2 C3 N2 176.8(2) . . . . ?
C1 C2 C3 C4 -3.9(3) . . . . ?
N2 C3 C4 C5 3.5(4) . . . . ?
C2 C3 C4 C5 -175.8(2) . . . . ?
N2 C3 C4 C9 -177.8(2) . . . . ?
C2 C3 C4 C9 2.9(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C5 C6 C7 Cl1 179.92(18) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
Cl1 C7 C8 C9 178.15(18) . . . . ?
C1 N1 C9 C8 179.1(2) . . . . ?
C1 N1 C9 C4 -1.5(3) . . . . ?
C7 C8 C9 N1 -178.0(2) . . . . ?
C7 C8 C9 C4 2.5(4) . . . . ?
C5 C4 C9 N1 178.5(2) . . . . ?
C3 C4 C9 N1 -0.2(4) . . . . ?
C5 C4 C9 C8 -2.1(3) . . . . ?
C3 C4 C9 C8 179.2(2) . . . . ?
C3 N2 C10 C11 -167.4(2) . . . . ?
N2 C10 C11 C12 179.2(2) . . . . ?
C10 C11 C12 C13 -174.0(2) . . . . ?
C9A N1A C1A C2A -0.4(4) . . . . ?
N1A C1A C2A C3A 0.9(4) . . . . ?
C10A N2A C3A C2A 2.3(4) . . . . ?
C10A N2A C3A C4A -176.7(2) . . . . ?
C1A C2A C3A N2A -178.8(2) . . . . ?
C1A C2A C3A C4A 0.3(3) . . . . ?
N2A C3A C4A C5A -2.8(4) . . . . ?
C2A C3A C4A C5A 178.2(2) . . . . ?
N2A C3A C4A C9A 177.2(2) . . . . ?
C2A C3A C4A C9A -1.8(3) . . . . ?
C9A C4A C5A C6A -0.2(4) . . . . ?
C3A C4A C5A C6A 179.7(2) . . . . ?
C4A C5A C6A C7A -0.7(4) . . . . ?
C5A C6A C7A C8A 0.7(4) . . . . ?
C5A C6A C7A Cl1A 179.40(19) . . . . ?
C6A C7A C8A C9A 0.2(4) . . . . ?
Cl1A C7A C8A C9A -178.42(18) . . . . ?
C1A N1A C9A C8A 179.9(2) . . . . ?
C1A N1A C9A C4A -1.3(3) . . . . ?
C7A C8A C9A N1A 177.6(2) . . . . ?
C7A C8A C9A C4A -1.2(4) . . . . ?
C5A C4A C9A N1A -177.6(2) . . . . ?
C3A C4A C9A N1A 2.5(3) . . . . ?
C5A C4A C9A C8A 1.2(3) . . . . ?
C3A C4A C9A C8A -178.8(2) . . . . ?
C3A N2A C10A C11A 173.4(2) . . . . ?
N2A C10A C11A C12A -173.8(2) . . . . ?
C10A C11A C12A C13A 178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.074

# Attachment '4_Cl.CIF'

data_Cl
_database_code_depnum_ccdc_archive 'CCDC 697894'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 Cl2 N2'
_chemical_formula_sum            'C11 H10 Cl2 N2'
_chemical_formula_weight         241.11

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc '

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   4.6442(12)
_cell_length_b                   17.670(4)
_cell_length_c                   13.313(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.024(2)
_cell_angle_gamma                90
_cell_volume                     1075.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    967
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      25.6

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.69050
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 9.8'
# Station 9.8: R. J. Cernik, W. Clegg, C. R. A. Catlow, G. Bushnell-Wye,
# J. V. Flaherty, G. N. Greaves, M. Hamichi, I. Burrows, D. J. Taylor
# and S. J. Teat,
# J. Synchotron Radiation 1997, 4, 279-286; 7, 40.
# Synchrotron chemical crystallography:
# W. Clegg, J. Chem. Soc., Dalton Trans. 2000, 3223-3232.

# Contact: W. Clegg (0191 222 6649), w.clegg@ncl.ac.uk
# R. W. Harrington (0191 222 6641), r.w.harrington@ncl.ac.uk

_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            3681
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.058
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.5
_diffrn_reflns_theta_max         25.0
_reflns_number_total             1913
_reflns_number_gt                1889
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2, Bruker'
# AXS Inc., Madison, USA, 2004
_computing_cell_refinement       'SAINT, Bruker'
# AXS Inc., Madison, USA, 2004
_computing_data_reduction        'SAINT, Bruker'
#AXS Inc., Madison, USA, 2004'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0679P)²+0.0079P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_number_reflns         1913
_refine_ls_number_parameters     139
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.038
_refine_ls_wR_factor_ref         0.105
_refine_ls_wR_factor_gt          0.104
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_restrained_S_all      1.11
_refine_ls_shift/su_max          <0.001
_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 -0.03321(12) 0.30872(4) 0.34632(5) 0.0233(2) Uani 1 1 d . . .
Cl2 Cl 0.56584(13) 0.73633(4) 0.05279(5) 0.0222(2) Uani 1 1 d . . .
N1 N 0.7012(6) 0.51598(14) 0.46306(18) 0.0208(5) Uani 1 1 d . . .
N2 N 0.7814(5) 0.57656(13) 0.16188(16) 0.0176(5) Uani 1 1 d D . .
H2N H 0.7206 0.5450 0.1115 0.021 Uiso 1 1 d D . .
C1 C 0.8708(7) 0.57170(17) 0.4416(2) 0.0220(6) Uani 1 1 d . . .
H1 H 0.9791 0.5983 0.4978 0.026 Uiso 1 1 calc R . .
C2 C 0.9061(6) 0.59516(15) 0.3444(2) 0.0192(6) Uani 1 1 d . . .
H2 H 1.0317 0.6364 0.3365 0.023 Uiso 1 1 calc R . .
C3 C 0.7552(6) 0.55756(15) 0.2588(2) 0.0165(5) Uani 1 1 d . . .
C4 C 0.5637(6) 0.49765(15) 0.2775(2) 0.0156(5) Uani 1 1 d . . .
C5 C 0.3887(6) 0.45626(16) 0.1982(2) 0.0185(6) Uani 1 1 d . . .
H5 H 0.3977 0.4680 0.1292 0.022 Uiso 1 1 calc R . .
C6 C 0.2072(6) 0.39983(16) 0.2194(2) 0.0200(6) Uani 1 1 d . . .
H6 H 0.0912 0.3727 0.1654 0.024 Uiso 1 1 calc R . .
C7 C 0.1927(6) 0.38221(16) 0.3206(2) 0.0173(6) Uani 1 1 d . . .
C8 C 0.3564(6) 0.42090(15) 0.4002(2) 0.0175(6) Uani 1 1 d . . .
H8 H 0.3431 0.4082 0.4686 0.021 Uiso 1 1 calc R . .
C9 C 0.5437(6) 0.47943(15) 0.3799(2) 0.0161(5) Uani 1 1 d . . .
C10 C 0.9815(6) 0.63476(16) 0.1396(2) 0.0190(6) Uani 1 1 d . . .
H10A H 1.0169 0.6275 0.0690 0.023 Uiso 1 1 calc R . .
H10B H 1.1708 0.6283 0.1861 0.023 Uiso 1 1 calc R . .
C11 C 0.8739(6) 0.71497(16) 0.1501(2) 0.0195(6) Uani 1 1 d . . .
H11A H 1.0342 0.7510 0.1453 0.023 Uiso 1 1 calc R . .
H11B H 0.8176 0.7212 0.2180 0.023 Uiso 1 1 calc R . .


_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
Cl1 C7 1.741(3) . ?
Cl2 C11 1.795(3) . ?
N1 C1 1.323(4) . ?
N1 C9 1.377(4) . ?
N2 C3 1.359(4) . ?
N2 C10 1.451(3) . ?
N2 H2N 0.8800 . ?
C1 C2 1.395(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.432(4) . ?
C4 C5 1.418(4) . ?
C4 C9 1.420(4) . ?
C5 C6 1.366(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C8 C9 1.408(4) . ?
C8 H8 0.9500 . ?
C10 C11 1.517(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
C1 N1 C9 115.3(2) . . ?
C3 N2 C10 122.4(2) . . ?
C3 N2 H2N 119.8 . . ?
C10 N2 H2N 115.1 . . ?
N1 C1 C2 126.3(3) . . ?
N1 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C3 C2 122.8(2) . . ?
N2 C3 C4 120.6(2) . . ?
C2 C3 C4 116.7(2) . . ?
C5 C4 C9 118.2(3) . . ?
C5 C4 C3 123.0(3) . . ?
C9 C4 C3 118.7(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 Cl1 119.4(2) . . ?
C6 C7 Cl1 119.3(2) . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C8 116.7(2) . . ?
N1 C9 C4 123.5(3) . . ?
C8 C9 C4 119.8(2) . . ?
N2 C10 C11 114.2(2) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 Cl2 111.3(2) . . ?
C10 C11 H11A 109.4 . . ?
Cl2 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
Cl2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?

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 N1 C1 C2 -1.0(4) . . . . ?
N1 C1 C2 C3 -0.8(5) . . . . ?
C10 N2 C3 C2 3.6(4) . . . . ?
C10 N2 C3 C4 -177.4(2) . . . . ?
C1 C2 C3 N2 -179.1(3) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
N2 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 177.7(2) . . . . ?
N2 C3 C4 C9 179.8(2) . . . . ?
C2 C3 C4 C9 -1.2(4) . . . . ?
C9 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C6 -179.5(2) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C5 C6 C7 Cl1 -178.5(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
Cl1 C7 C8 C9 178.79(19) . . . . ?
C1 N1 C9 C8 -178.7(2) . . . . ?
C1 N1 C9 C4 1.7(4) . . . . ?
C7 C8 C9 N1 179.9(2) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
C5 C4 C9 N1 -179.5(3) . . . . ?
C3 C4 C9 N1 -0.6(4) . . . . ?
C5 C4 C9 C8 0.8(4) . . . . ?
C3 C4 C9 C8 179.8(2) . . . . ?
C3 N2 C10 C11 -77.8(3) . . . . ?
N2 C10 C11 Cl2 -68.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.097

# Attachment '5_azide.CIF'

data_azide
_database_code_depnum_ccdc_archive 'CCDC 697895'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 Cl N5'
_chemical_formula_sum            'C11 H10 Cl N5'
_chemical_formula_weight         247.69

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

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

_cell_length_a                   13.0426(5)
_cell_length_b                   7.8693(2)
_cell_length_c                   22.6276(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2322.41(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2928
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16466
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.4
_reflns_number_total             2630
_reflns_number_gt                2120
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0184P)²+3.7962P] where P=(Fo²+2Fc²)/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         2630
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.051
_refine_ls_wR_factor_ref         0.105
_refine_ls_wR_factor_gt          0.096
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_refine_ls_shift/su_max          0.001
_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 0.18786(5) 0.15546(8) 0.55167(2) 0.02836(16) Uani 1 1 d . . .
N1 N 0.04322(14) 0.4454(2) 0.73332(8) 0.0221(4) Uani 1 1 d . . .
N2 N 0.33271(14) 0.4890(2) 0.81559(8) 0.0195(4) Uani 1 1 d D . .
H2N H 0.3893 0.4582 0.7973 0.023 Uiso 1 1 d D . .
N3 N 0.38215(17) 0.3364(3) 0.93286(8) 0.0300(5) Uani 1 1 d . . .
N4 N 0.42405(16) 0.3219(3) 0.98157(9) 0.0280(5) Uani 1 1 d . . .
N5 N 0.46696(18) 0.2953(3) 1.02406(10) 0.0420(6) Uani 1 1 d . . .
C1 C 0.05692(17) 0.5176(3) 0.78566(10) 0.0222(5) Uani 1 1 d . . .
H1 H -0.0024 0.5601 0.8050 0.027 Uiso 1 1 calc R . .
C2 C 0.15004(17) 0.5371(3) 0.81489(10) 0.0202(5) Uani 1 1 d . . .
H2 H 0.1524 0.5929 0.8521 0.024 Uiso 1 1 calc R . .
C3 C 0.24005(16) 0.4747(3) 0.78950(9) 0.0161(4) Uani 1 1 d . . .
C4 C 0.22938(16) 0.3926(3) 0.73261(9) 0.0159(4) Uani 1 1 d . . .
C5 C 0.31378(16) 0.3258(3) 0.70103(9) 0.0184(4) Uani 1 1 d . . .
H5 H 0.3802 0.3299 0.7182 0.022 Uiso 1 1 calc R . .
C6 C 0.30170(17) 0.2550(3) 0.64600(10) 0.0211(5) Uani 1 1 d . . .
H6 H 0.3590 0.2116 0.6250 0.025 Uiso 1 1 calc R . .
C7 C 0.20268(18) 0.2482(3) 0.62136(9) 0.0203(5) Uani 1 1 d . . .
C8 C 0.11901(17) 0.3108(3) 0.64994(9) 0.0197(4) Uani 1 1 d . . .
H8 H 0.0533 0.3053 0.6319 0.024 Uiso 1 1 calc R . .
C9 C 0.13036(16) 0.3843(3) 0.70677(9) 0.0180(4) Uani 1 1 d . . .
C10 C 0.34908(18) 0.5853(3) 0.86968(10) 0.0225(5) Uani 1 1 d . . .
H10A H 0.3093 0.6923 0.8673 0.027 Uiso 1 1 calc R . .
H10B H 0.4225 0.6160 0.8723 0.027 Uiso 1 1 calc R . .
C11 C 0.31863(18) 0.4918(3) 0.92580(10) 0.0237(5) Uani 1 1 d . . .
H11A H 0.3284 0.5672 0.9604 0.028 Uiso 1 1 calc R . .
H11B H 0.2453 0.4601 0.9238 0.028 Uiso 1 1 calc R . .


_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
Cl1 C7 1.748(2) . ?
N1 C1 1.326(3) . ?
N1 C9 1.372(3) . ?
N2 C3 1.350(3) . ?
N2 C10 1.456(3) . ?
N2 H2N 0.8800 . ?
N3 N4 1.235(3) . ?
N3 C11 1.486(3) . ?
N4 N5 1.132(3) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.447(3) . ?
C4 C5 1.414(3) . ?
C4 C9 1.419(3) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.361(3) . ?
C8 C9 1.418(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
C1 N1 C9 115.44(19) . . ?
C3 N2 C10 122.86(18) . . ?
C3 N2 H2N 121.5 . . ?
C10 N2 H2N 114.5 . . ?
N4 N3 C11 114.76(19) . . ?
N5 N4 N3 173.4(3) . . ?
N1 C1 C2 126.1(2) . . ?
N1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C3 C2 122.92(19) . . ?
N2 C3 C4 120.83(19) . . ?
C2 C3 C4 116.25(19) . . ?
C5 C4 C9 118.90(19) . . ?
C5 C4 C3 122.74(19) . . ?
C9 C4 C3 118.33(19) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 Cl1 119.42(17) . . ?
C6 C7 Cl1 118.34(17) . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C8 116.97(19) . . ?
N1 C9 C4 123.86(19) . . ?
C8 C9 C4 119.17(19) . . ?
N2 C10 C11 114.31(19) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N3 C11 C10 110.04(19) . . ?
N3 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?

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
C11 N3 N4 N5 -175(2) . . . . ?
C9 N1 C1 C2 0.5(3) . . . . ?
N1 C1 C2 C3 -1.3(4) . . . . ?
C10 N2 C3 C2 -6.3(3) . . . . ?
C10 N2 C3 C4 173.50(19) . . . . ?
C1 C2 C3 N2 -179.8(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
N2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C5 178.9(2) . . . . ?
N2 C3 C4 C9 -178.74(19) . . . . ?
C2 C3 C4 C9 1.1(3) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C6 -177.2(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 Cl1 -179.21(17) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
Cl1 C7 C8 C9 179.26(16) . . . . ?
C1 N1 C9 C8 -178.2(2) . . . . ?
C1 N1 C9 C4 1.2(3) . . . . ?
C7 C8 C9 N1 179.9(2) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C5 C4 C9 N1 -179.9(2) . . . . ?
C3 C4 C9 N1 -1.9(3) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C3 C4 C9 C8 177.38(19) . . . . ?
C3 N2 C10 C11 80.0(3) . . . . ?
N4 N3 C11 C10 128.5(2) . . . . ?
N2 C10 C11 N3 62.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.4
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.062

# Attachment '6_CH2CH2OH.CIF'

data_CH2CH2OH
_database_code_depnum_ccdc_archive 'CCDC 697896'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 Cl N2 O'
_chemical_formula_sum            'C11 H11 Cl N2 O'
_chemical_formula_weight         222.67

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'
H H 0.0000 0.0000 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn '

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                   4.5721(1)
_cell_length_b                   14.8383(6)
_cell_length_c                   14.8932(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.546(3)
_cell_angle_gamma                90
_cell_volume                     1008.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13921
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2296
_reflns_number_gt                1624
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0447P)²+0.4254P] where P=(Fo²+2Fc²)/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         2296
_refine_ls_number_parameters     142
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.041
_refine_ls_wR_factor_ref         0.104
_refine_ls_wR_factor_gt          0.091
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          <0.001
_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 1.08404(11) 0.09498(4) 0.42344(3) 0.02970(17) Uani 1 1 d . . .
O1 O -0.0263(3) 0.05329(9) -0.09674(9) 0.0227(3) Uani 1 1 d D . .
H1O H -0.0115 0.0863 -0.1421 0.034 Uiso 1 1 d D . .
N1 N 0.4712(4) 0.33259(11) 0.25709(11) 0.0240(4) Uani 1 1 d . . .
N2 N 0.0711(3) 0.14634(11) 0.07666(11) 0.0212(4) Uani 1 1 d D . .
H2N H 0.0755 0.0887 0.0904 0.025 Uiso 1 1 d D . .
C1 C 0.2803(4) 0.35592(13) 0.19085(13) 0.0259(5) Uani 1 1 d . . .
H1 H 0.2329 0.4181 0.1854 0.031 Uiso 1 1 calc R . .
C2 C 0.1430(4) 0.29777(13) 0.12867(13) 0.0228(4) Uani 1 1 d . . .
H2 H 0.0105 0.3205 0.0825 0.027 Uiso 1 1 calc R . .
C3 C 0.2009(4) 0.20630(12) 0.13447(12) 0.0177(4) Uani 1 1 d . . .
C4 C 0.4151(4) 0.17727(12) 0.20328(12) 0.0182(4) Uani 1 1 d . . .
C5 C 0.5080(4) 0.08725(13) 0.21360(13) 0.0213(4) Uani 1 1 d . . .
H5 H 0.4266 0.0428 0.1735 0.026 Uiso 1 1 calc R . .
C6 C 0.7115(4) 0.06206(13) 0.27956(13) 0.0222(4) Uani 1 1 d . . .
H6 H 0.7711 0.0009 0.2856 0.027 Uiso 1 1 calc R . .
C7 C 0.8310(4) 0.12808(13) 0.33829(12) 0.0206(4) Uani 1 1 d . . .
C8 C 0.7517(4) 0.21577(13) 0.33010(12) 0.0206(4) Uani 1 1 d . . .
H8 H 0.8384 0.2592 0.3704 0.025 Uiso 1 1 calc R . .
C9 C 0.5416(4) 0.24313(13) 0.26232(12) 0.0194(4) Uani 1 1 d . . .
C10 C -0.1488(4) 0.17288(13) 0.00730(12) 0.0202(4) Uani 1 1 d . . .
H10A H -0.0654 0.2183 -0.0325 0.024 Uiso 1 1 calc R . .
H10B H -0.3178 0.2005 0.0354 0.024 Uiso 1 1 calc R . .
C11 C -0.2501(4) 0.09223(13) -0.04726(13) 0.0224(4) Uani 1 1 d . . .
H11A H -0.3246 0.0461 -0.0064 0.027 Uiso 1 1 calc R . .
H11B H -0.4148 0.1105 -0.0897 0.027 Uiso 1 1 calc R . .


_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
Cl1 C7 1.7339(19) . ?
O1 C11 1.420(2) . ?
O1 H1O 0.8400 . ?
N1 C1 1.322(3) . ?
N1 C9 1.367(2) . ?
N2 C3 1.350(2) . ?
N2 C10 1.451(2) . ?
N2 H2N 0.8799 . ?
C1 C2 1.387(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.439(3) . ?
C4 C5 1.407(3) . ?
C4 C9 1.414(3) . ?
C5 C6 1.363(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.354(3) . ?
C8 C9 1.410(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.503(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
C11 O1 H1O 106.1 . . ?
C1 N1 C9 116.03(16) . . ?
C3 N2 C10 122.22(16) . . ?
C3 N2 H2N 119.3 . . ?
C10 N2 H2N 115.7 . . ?
N1 C1 C2 125.86(18) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C3 C2 C1 119.44(18) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
N2 C3 C2 122.13(17) . . ?
N2 C3 C4 120.65(16) . . ?
C2 C3 C4 117.18(17) . . ?
C5 C4 C9 118.63(17) . . ?
C5 C4 C3 123.33(17) . . ?
C9 C4 C3 118.03(17) . . ?
C6 C5 C4 121.81(18) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.73(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 121.57(18) . . ?
C8 C7 Cl1 120.05(15) . . ?
C6 C7 Cl1 118.38(15) . . ?
C7 C8 C9 120.53(17) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C8 117.91(17) . . ?
N1 C9 C4 123.37(17) . . ?
C8 C9 C4 118.73(17) . . ?
N2 C10 C11 110.22(15) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C10 113.35(15) . . ?
O1 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
O1 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?

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 N1 C1 C2 1.6(3) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
C10 N2 C3 C2 -3.2(3) . . . . ?
C10 N2 C3 C4 179.07(16) . . . . ?
C1 C2 C3 N2 179.12(18) . . . . ?
C1 C2 C3 C4 -3.1(3) . . . . ?
N2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 C5 -176.19(18) . . . . ?
N2 C3 C4 C9 -179.47(17) . . . . ?
C2 C3 C4 C9 2.7(3) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C6 180.00(17) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C5 C6 C7 Cl1 178.68(15) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
Cl1 C7 C8 C9 -178.64(14) . . . . ?
C1 N1 C9 C8 177.91(17) . . . . ?
C1 N1 C9 C4 -1.9(3) . . . . ?
C7 C8 C9 N1 -179.73(18) . . . . ?
C7 C8 C9 C4 0.1(3) . . . . ?
C5 C4 C9 N1 178.74(18) . . . . ?
C3 C4 C9 N1 -0.2(3) . . . . ?
C5 C4 C9 C8 -1.1(3) . . . . ?
C3 C4 C9 C8 179.99(16) . . . . ?
C3 N2 C10 C11 179.24(16) . . . . ?
N2 C10 C11 O1 -64.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.30
_refine_diff_density_rms         0.065

# Attachment '7_racemic.CIF'

data_racemic
_database_code_depnum_ccdc_archive 'CCDC 697897'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Cl N2 O'
_chemical_formula_sum            'C13 H15 Cl N2 O'
_chemical_formula_weight         250.72

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   8.9290(3)
_cell_length_b                   15.0394(5)
_cell_length_c                   9.2127(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.198(2)
_cell_angle_gamma                90
_cell_volume                     1193.88(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2797
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14685
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2722
_reflns_number_gt                2403
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0321P)²+0.9182P] where P=(Fo²+2Fc²)/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         2722
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.090
_refine_ls_wR_factor_gt          0.086
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_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 -0.12317(4) 0.57665(3) 0.08343(4) 0.02147(12) Uani 1 1 d . . .
O1 O 0.53589(12) 0.14003(7) 0.88664(12) 0.0190(2) Uani 1 1 d D . .
H1O H 0.6315 0.1511 0.9121 0.029 Uiso 1 1 d D . .
N1 N -0.14597(14) 0.33202(9) 0.45916(14) 0.0174(3) Uani 1 1 d . . .
N2 N 0.34189(14) 0.31236(9) 0.60869(14) 0.0187(3) Uani 1 1 d D . .
H2N H 0.3953 0.3375 0.5520 0.022 Uiso 1 1 d D . .
C1 C -0.07401(18) 0.27812(10) 0.56941(17) 0.0182(3) Uani 1 1 d . . .
H1 H -0.1374 0.2427 0.6148 0.022 Uiso 1 1 calc R . .
C2 C 0.08618(17) 0.26873(10) 0.62469(16) 0.0167(3) Uani 1 1 d . . .
H2 H 0.1277 0.2280 0.7038 0.020 Uiso 1 1 calc R . .
C3 C 0.18478(16) 0.31932(10) 0.56345(16) 0.0140(3) Uani 1 1 d . . .
C4 C 0.11285(16) 0.38219(9) 0.44795(15) 0.0131(3) Uani 1 1 d . . .
C5 C 0.19864(17) 0.44408(10) 0.38554(17) 0.0164(3) Uani 1 1 d . . .
H5 H 0.3087 0.4446 0.4199 0.020 Uiso 1 1 calc R . .
C6 C 0.12585(18) 0.50299(10) 0.27686(17) 0.0176(3) Uani 1 1 d . . .
H6 H 0.1848 0.5443 0.2366 0.021 Uiso 1 1 calc R . .
C7 C -0.03687(17) 0.50198(10) 0.22506(16) 0.0156(3) Uani 1 1 d . . .
C8 C -0.12511(17) 0.44530(10) 0.28400(16) 0.0161(3) Uani 1 1 d . . .
H8 H -0.2350 0.4464 0.2483 0.019 Uiso 1 1 calc R . .
C9 C -0.05184(16) 0.38477(9) 0.39882(16) 0.0138(3) Uani 1 1 d . . .
C10 C 0.42806(17) 0.27641(10) 0.75468(17) 0.0180(3) Uani 1 1 d . . .
H10 H 0.3598 0.2805 0.8248 0.022 Uiso 1 1 calc R . .
C11 C 0.46973(17) 0.17824(10) 0.74232(17) 0.0183(3) Uani 1 1 d . . .
H11A H 0.3751 0.1448 0.6914 0.022 Uiso 1 1 calc R . .
H11B H 0.5445 0.1732 0.6802 0.022 Uiso 1 1 calc R . .
C12 C 0.57109(18) 0.33371(11) 0.81834(18) 0.0209(3) Uani 1 1 d . . .
H12A H 0.6318 0.3073 0.9142 0.025 Uiso 1 1 calc R . .
H12B H 0.6371 0.3331 0.7472 0.025 Uiso 1 1 calc R . .
C13 C 0.5320(2) 0.42974(11) 0.8465(2) 0.0267(4) Uani 1 1 d . . .
H13A H 0.6282 0.4632 0.8867 0.040 Uiso 1 1 calc R . .
H13B H 0.4692 0.4311 0.9191 0.040 Uiso 1 1 calc R . .
H13C H 0.4736 0.4567 0.7517 0.040 Uiso 1 1 calc R . .


_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
Cl1 C7 1.7408(15) . ?
O1 C11 1.4266(18) . ?
O1 H1O 0.8400 . ?
N1 C1 1.3265(19) . ?
N1 C9 1.3747(19) . ?
N2 C3 1.3587(19) . ?
N2 C10 1.4666(18) . ?
N2 H2N 0.8799 . ?
C1 C2 1.394(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.442(2) . ?
C4 C5 1.419(2) . ?
C4 C9 1.4212(19) . ?
C5 C6 1.367(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(2) . ?
C8 C9 1.419(2) . ?
C8 H8 0.9500 . ?
C10 C12 1.525(2) . ?
C10 C11 1.534(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C11 O1 H1O 108.8 . . ?
C1 N1 C9 115.95(13) . . ?
C3 N2 C10 124.13(13) . . ?
C3 N2 H2N 117.5 . . ?
C10 N2 H2N 117.9 . . ?
N1 C1 C2 125.90(14) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C3 C2 C1 119.64(14) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N2 C3 C2 123.10(13) . . ?
N2 C3 C4 120.08(13) . . ?
C2 C3 C4 116.82(13) . . ?
C5 C4 C9 118.45(13) . . ?
C5 C4 C3 123.05(13) . . ?
C9 C4 C3 118.45(13) . . ?
C6 C5 C4 121.21(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.50(14) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.62(14) . . ?
C8 C7 Cl1 120.82(12) . . ?
C6 C7 Cl1 117.55(11) . . ?
C7 C8 C9 119.70(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C8 117.42(13) . . ?
N1 C9 C4 123.14(13) . . ?
C8 C9 C4 119.43(13) . . ?
N2 C10 C12 109.24(13) . . ?
N2 C10 C11 111.46(12) . . ?
C12 C10 C11 112.18(12) . . ?
N2 C10 H10 107.9 . . ?
C12 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
O1 C11 C10 111.57(12) . . ?
O1 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C10 113.27(13) . . ?
C13 C12 H12A 108.9 . . ?
C10 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C10 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 N1 C1 C2 -2.2(2) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
C10 N2 C3 C2 -21.7(2) . . . . ?
C10 N2 C3 C4 157.59(14) . . . . ?
C1 C2 C3 N2 -178.33(14) . . . . ?
C1 C2 C3 C4 2.4(2) . . . . ?
N2 C3 C4 C5 -5.5(2) . . . . ?
C2 C3 C4 C5 173.80(14) . . . . ?
N2 C3 C4 C9 177.22(13) . . . . ?
C2 C3 C4 C9 -3.50(19) . . . . ?
C9 C4 C5 C6 -2.3(2) . . . . ?
C3 C4 C5 C6 -179.56(14) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C5 C6 C7 Cl1 -178.51(11) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
Cl1 C7 C8 C9 179.67(11) . . . . ?
C1 N1 C9 C8 -178.00(13) . . . . ?
C1 N1 C9 C4 0.8(2) . . . . ?
C7 C8 C9 N1 177.08(13) . . . . ?
C7 C8 C9 C4 -1.8(2) . . . . ?
C5 C4 C9 N1 -175.47(13) . . . . ?
C3 C4 C9 N1 2.0(2) . . . . ?
C5 C4 C9 C8 3.4(2) . . . . ?
C3 C4 C9 C8 -179.22(13) . . . . ?
C3 N2 C10 C12 -138.23(15) . . . . ?
C3 N2 C10 C11 97.24(17) . . . . ?
N2 C10 C11 O1 -172.58(12) . . . . ?
C12 C10 C11 O1 64.56(16) . . . . ?
N2 C10 C12 C13 61.63(18) . . . . ?
C11 C10 C12 C13 -174.26(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.052

# Attachment '8_chiral.CIF'

data_chiral
_database_code_depnum_ccdc_archive 'CCDC 697898'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Cl N2 O'
_chemical_formula_sum            'C13 H15 Cl N2 O'
_chemical_formula_weight         250.72

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb '

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

_cell_length_a                   8.7612(3)
_cell_length_b                   7.0756(1)
_cell_length_c                   9.6622(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.644(1)
_cell_angle_gamma                90
_cell_volume                     596.06(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1445
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8587
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.0
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2706
_reflns_number_gt                2601
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_chemical_absolute_configuration rm

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.1464P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_number_reflns         2706
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.030
_refine_ls_wR_factor_ref         0.073
_refine_ls_wR_factor_gt          0.071
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_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 1.11691(4) 0.29708(6) 0.60467(3) 0.02007(10) Uani 1 1 d . . .
O1 O 0.53033(12) 0.61227(16) -0.15388(12) 0.0174(2) Uani 1 1 d D . .
H1O H 0.6242 0.6243 -0.1281 0.026 Uiso 1 1 d D . .
N1 N 1.16399(14) 0.18760(18) 0.09238(13) 0.0131(3) Uani 1 1 d . . .
N2 N 0.69112(13) 0.2749(2) -0.02025(12) 0.0128(3) Uani 1 1 d D . .
H2N H 0.6263 0.2487 0.0411 0.015 Uiso 1 1 d D . .
C1 C 1.10172(17) 0.1833(2) -0.03890(16) 0.0144(3) Uani 1 1 d . . .
H1 H 1.1689 0.1626 -0.1088 0.017 Uiso 1 1 calc R . .
C2 C 0.94665(17) 0.2065(2) -0.08257(15) 0.0139(3) Uani 1 1 d . . .
H2 H 0.9120 0.2007 -0.1788 0.017 Uiso 1 1 calc R . .
C3 C 0.84203(17) 0.23842(19) 0.01482(15) 0.0119(3) Uani 1 1 d . . .
C4 C 0.90394(17) 0.24215(19) 0.15942(15) 0.0119(3) Uani 1 1 d . . .
C5 C 0.81293(16) 0.2804(2) 0.26961(14) 0.0138(3) Uani 1 1 d . . .
H5 H 0.7052 0.2951 0.2497 0.017 Uiso 1 1 calc R . .
C6 C 0.87729(16) 0.2965(3) 0.40450(14) 0.0155(3) Uani 1 1 d . . .
H6 H 0.8151 0.3231 0.4773 0.019 Uiso 1 1 calc R . .
C7 C 1.03652(17) 0.2731(2) 0.43324(14) 0.0150(3) Uani 1 1 d . . .
C8 C 1.12892(18) 0.2321(2) 0.33139(16) 0.0142(3) Uani 1 1 d . . .
H8 H 1.2357 0.2128 0.3542 0.017 Uiso 1 1 calc R . .
C9 C 1.06414(17) 0.2184(2) 0.19075(15) 0.0125(3) Uani 1 1 d . . .
C10 C 0.62126(15) 0.2814(2) -0.16458(14) 0.0123(3) Uani 1 1 d . . .
H10 H 0.6994 0.3296 -0.2247 0.015 Uiso 1 1 calc R . .
C11 C 0.48723(17) 0.4196(2) -0.17326(16) 0.0142(3) Uani 1 1 d . . .
H11A H 0.4281 0.4062 -0.2655 0.017 Uiso 1 1 calc R . .
H11B H 0.4185 0.3847 -0.1020 0.017 Uiso 1 1 calc R . .
C12 C 0.57046(18) 0.0832(2) -0.21585(16) 0.0166(3) Uani 1 1 d . . .
H12A H 0.6519 -0.0084 -0.1841 0.020 Uiso 1 1 calc R . .
H12B H 0.4770 0.0476 -0.1721 0.020 Uiso 1 1 calc R . .
C13 C 0.5369(2) 0.0665(3) -0.37377(17) 0.0236(4) Uani 1 1 d . . .
H13A H 0.5053 -0.0631 -0.3981 0.035 Uiso 1 1 calc R . .
H13B H 0.6296 0.0978 -0.4182 0.035 Uiso 1 1 calc R . .
H13C H 0.4545 0.1542 -0.4062 0.035 Uiso 1 1 calc R . .


_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
Cl1 C7 1.7432(14) . ?
O1 C11 1.4218(19) . ?
O1 H1O 0.8401 . ?
N1 C1 1.3309(19) . ?
N1 C9 1.3710(19) . ?
N2 C3 1.3570(19) . ?
N2 C10 1.4675(16) . ?
N2 H2N 0.8801 . ?
C1 C2 1.392(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4484(19) . ?
C4 C9 1.416(2) . ?
C4 C5 1.418(2) . ?
C5 C6 1.3730(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(2) . ?
C8 C9 1.424(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.524(2) . ?
C10 C12 1.538(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.530(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C11 O1 H1O 112.1 . . ?
C1 N1 C9 115.76(13) . . ?
C3 N2 C10 123.24(12) . . ?
C3 N2 H2N 118.0 . . ?
C10 N2 H2N 114.2 . . ?
N1 C1 C2 125.63(14) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C1 C2 C3 120.07(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C3 C2 123.44(13) . . ?
N2 C3 C4 120.04(13) . . ?
C2 C3 C4 116.42(13) . . ?
C9 C4 C5 118.74(13) . . ?
C9 C4 C3 118.24(13) . . ?
C5 C4 C3 122.89(13) . . ?
C6 C5 C4 121.33(13) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.00(13) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 122.01(13) . . ?
C8 C7 Cl1 119.52(12) . . ?
C6 C7 Cl1 118.47(11) . . ?
C7 C8 C9 119.57(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C4 123.85(13) . . ?
N1 C9 C8 116.81(13) . . ?
C4 C9 C8 119.31(13) . . ?
N2 C10 C11 108.62(11) . . ?
N2 C10 C12 110.98(12) . . ?
C11 C10 C12 111.73(11) . . ?
N2 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C12 C10 H10 108.5 . . ?
O1 C11 C10 114.50(12) . . ?
O1 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
O1 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C10 114.38(13) . . ?
C13 C12 H12A 108.7 . . ?
C10 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C10 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 N1 C1 C2 -0.2(2) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
C10 N2 C3 C2 1.1(2) . . . . ?
C10 N2 C3 C4 177.44(13) . . . . ?
C1 C2 C3 N2 175.42(14) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
N2 C3 C4 C9 -174.99(13) . . . . ?
C2 C3 C4 C9 1.56(19) . . . . ?
N2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C5 177.44(15) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 C6 -175.15(16) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 Cl1 179.16(15) . . . . ?
C6 C7 C8 C9 2.1(2) . . . . ?
Cl1 C7 C8 C9 -178.01(11) . . . . ?
C1 N1 C9 C4 0.9(2) . . . . ?
C1 N1 C9 C8 -177.25(13) . . . . ?
C5 C4 C9 N1 -177.63(14) . . . . ?
C3 C4 C9 N1 -1.6(2) . . . . ?
C5 C4 C9 C8 0.4(2) . . . . ?
C3 C4 C9 C8 176.50(12) . . . . ?
C7 C8 C9 N1 176.38(15) . . . . ?
C7 C8 C9 C4 -1.8(2) . . . . ?
C3 N2 C10 C11 -150.13(14) . . . . ?
C3 N2 C10 C12 86.66(16) . . . . ?
N2 C10 C11 O1 69.05(16) . . . . ?
C12 C10 C11 O1 -168.20(13) . . . . ?
N2 C10 C12 C13 -164.34(13) . . . . ?
C11 C10 C12 C13 74.27(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.049


