# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cs006
_audit_creation_date             2013-05-01
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H15 N2, C H O3'
_chemical_formula_sum            'C9 H16 N2 O3'
_chemical_formula_weight         200.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H16 N2 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.9516(3)
_cell_length_b                   8.1294(3)
_cell_length_c                   9.6234(4)
_cell_angle_alpha                74.586(4)
_cell_angle_beta                 80.157(4)
_cell_angle_gamma                83.657(3)
_cell_volume                     515.35(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9680
_cell_measurement_theta_min      4.7940
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.2834
_exptl_crystal_size_mid          0.1519
_exptl_crystal_size_min          0.1137
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8198
_diffrn_reflns_theta_full        72.06
_diffrn_reflns_theta_max         72.06
_diffrn_reflns_theta_min         4.82
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -45.0000  -33.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048   45.0000  -63.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   45.0000  116.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -45.0000   63.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -45.0000   63.0000 43

#__ type_ start__ end____ width___ exp.time_
  6 omega  -57.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000 -116.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega -115.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000 -116.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  116.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  146.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega  127.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  116.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  106.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   33.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   63.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega -113.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega  -55.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega   24.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048 -125.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   45.0000   33.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega    6.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   88.0000   34.1948 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  -92.00  -67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000  -33.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega  -55.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000 -146.0000 75

#__ type_ start__ end____ width___ exp.time_
 20 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -124.9277 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   22.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -65.5444 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -159.5750 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  124.1860 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   29.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   58.0167 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -18.6978 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   30.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  153.4449 103

#__ type_ start__ end____ width___ exp.time_
 27 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -121.9961 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   37.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -93.8165 29

#__ type_ start__ end____ width___ exp.time_
 29 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   72.7692 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  115.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   72.7692 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   47.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   64.0000   21.9531 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   43.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   67.0000  -52.8924 27

#__ type_ start__ end____ width___ exp.time_
 33 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000  -13.4032 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   47.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   52.0000 -155.7302 36

#__ type_ start__ end____ width___ exp.time_
 35 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   61.0000   53.6754 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   53.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   70.0000   77.3764 38

#__ type_ start__ end____ width___ exp.time_
 37 omega  118.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   46.0000  -17.3513 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   46.0000  -17.3513 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
 40 omega   83.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 41 omega   38.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 42 omega   81.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 43 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   87.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -61.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 45 omega  126.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 46 omega   86.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
 47 omega   32.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 48 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega  118.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 50 omega   78.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 51 omega   81.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
 52 omega   81.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 53 omega   81.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 54 omega   81.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 55 omega   37.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 56 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 57 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
 58 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   82.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
 60 omega   37.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000   90.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1531496000
_diffrn_orient_matrix_UB_12      0.0600133000
_diffrn_orient_matrix_UB_13      0.0707049000
_diffrn_orient_matrix_UB_21      0.1590084000
_diffrn_orient_matrix_UB_22      -0.1187326000
_diffrn_orient_matrix_UB_23      -0.0634686000
_diffrn_orient_matrix_UB_31      0.0457268000
_diffrn_orient_matrix_UB_32      0.1453458000
_diffrn_orient_matrix_UB_33      -0.1384308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1822
_reflns_number_total             2005
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.0911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1125
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates and stretchable bonds:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates and stretchable bonds:
 C1(H1)
2.c Idealised Me refined as rotating group with stretchable bonds:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C1 C 0.07796(19) 1.05138(16) 0.27136(14) 0.0448(3) Uani 1 1 d . . .
H1 H 0.1654(16) 1.1177(12) 0.2903(4) 0.054 Uiso 1 1 calc R . .
C2 C -0.15853(19) 0.97052(17) 0.18178(14) 0.0448(3) Uani 1 1 d . . .
C3 C -0.08414(19) 0.83090(17) 0.27409(14) 0.0451(3) Uani 1 1 d . . .
C4 C -0.0883(2) 1.28427(18) 0.10131(18) 0.0601(4) Uani 1 1 d . . .
H4A H -0.2007(16) 1.3303(7) 0.1422(9) 0.090 Uiso 1 1 calc R . .
H4B H -0.0967(18) 1.2879(2) 0.0080(12) 0.090 Uiso 1 1 calc R . .
H4C H 0.0123(15) 1.3442(8) 0.1036(12) 0.090 Uiso 1 1 calc R . .
C5 C -0.3173(2) 0.9903(2) 0.09195(17) 0.0580(4) Uani 1 1 d . . .
H5A H -0.4225(14) 1.0678(15) 0.1229(9) 0.087 Uiso 1 1 calc R . .
H5B H -0.3672(13) 0.8796(12) 0.1041(10) 0.087 Uiso 1 1 calc R . .
H5C H -0.2662(7) 1.0365(15) -0.0099(11) 0.087 Uiso 1 1 calc R . .
C6 C -0.1411(2) 0.65156(18) 0.32134(18) 0.0602(4) Uani 1 1 d . . .
H6A H -0.0285(14) 0.5761(9) 0.3061(13) 0.090 Uiso 1 1 calc R . .
H6B H -0.2372(17) 0.6380(5) 0.2659(12) 0.090 Uiso 1 1 calc R . .
H6C H -0.1941(18) 0.6252(6) 0.4225(12) 0.090 Uiso 1 1 calc R . .
C7 C 0.1841(2) 0.77017(19) 0.43230(16) 0.0555(4) Uani 1 1 d . . .
H7A H 0.2474(8) 0.6762(12) 0.3904(5) 0.067 Uiso 1 1 calc R . .
H7B H 0.0979(11) 0.7197(7) 0.5225(11) 0.067 Uiso 1 1 calc R . .
C8 C 0.3380(2) 0.8600(2) 0.46881(19) 0.0680(5) Uani 1 1 d . . .
H8A H 0.4321(16) 0.9075(17) 0.3765(11) 0.102 Uiso 1 1 calc R . .
H8B H 0.4134(16) 0.7758(11) 0.5428(14) 0.102 Uiso 1 1 calc R . .
H8C H 0.2735(8) 0.9579(16) 0.5119(15) 0.102 Uiso 1 1 calc R . .
C9 C 0.35562(19) 0.41210(17) 0.19785(16) 0.0499(3) Uani 1 1 d . . .
N1 N 0.06413(15) 0.88465(13) 0.32827(11) 0.0435(3) Uani 1 1 d . . .
N2 N -0.05547(15) 1.10675(13) 0.18242(12) 0.0444(3) Uani 1 1 d . . .
O1 O 0.4357(2) 0.56260(16) 0.16901(14) 0.0736(4) Uani 1 1 d . . .
H1A H 0.507(3) 0.5869(16) 0.073(3) 0.110 Uiso 1 1 calc R . .
O2 O 0.37580(17) 0.34043(14) 0.09415(13) 0.0705(4) Uani 1 1 d . . .
O3 O 0.26596(18) 0.35692(16) 0.32029(13) 0.0722(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0465(6) 0.0415(7) 0.0467(7) -0.0108(5) -0.0078(5) -0.0037(5)
C2 0.0473(7) 0.0435(7) 0.0454(7) -0.0147(5) -0.0076(5) -0.0008(5)
C3 0.0495(7) 0.0419(7) 0.0454(7) -0.0136(5) -0.0068(5) -0.0034(5)
C4 0.0670(9) 0.0412(8) 0.0676(10) -0.0022(7) -0.0191(7) 0.0007(6)
C5 0.0563(8) 0.0614(9) 0.0620(9) -0.0203(7) -0.0209(7) 0.0021(7)
C6 0.0715(9) 0.0420(8) 0.0689(10) -0.0130(7) -0.0136(8) -0.0083(7)
C7 0.0655(9) 0.0506(8) 0.0492(8) -0.0087(6) -0.0185(6) 0.0080(7)
C8 0.0580(9) 0.0848(12) 0.0601(9) -0.0117(8) -0.0197(7) 0.0007(8)
C9 0.0435(7) 0.0451(7) 0.0615(9) -0.0132(6) -0.0106(6) -0.0015(5)
N1 0.0477(6) 0.0407(6) 0.0417(6) -0.0090(4) -0.0090(4) -0.0004(4)
N2 0.0477(6) 0.0381(6) 0.0462(6) -0.0081(4) -0.0087(5) -0.0011(4)
O1 0.0950(9) 0.0661(7) 0.0679(7) -0.0284(6) 0.0013(6) -0.0324(6)
O2 0.0802(8) 0.0565(7) 0.0777(8) -0.0301(6) 0.0140(6) -0.0244(6)
O3 0.0826(8) 0.0736(8) 0.0584(7) -0.0116(6) -0.0033(6) -0.0198(6)

_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
C1 N1 1.3276(17) . ?
C1 N2 1.3304(17) . ?
C2 C3 1.3551(19) . ?
C2 C5 1.4850(19) . ?
C2 N2 1.3858(17) . ?
C3 C6 1.4840(19) . ?
C3 N1 1.3891(17) . ?
C4 N2 1.4606(17) . ?
C7 C8 1.497(2) . ?
C7 N1 1.4771(17) . ?
C9 O1 1.3421(18) . ?
C9 O2 1.2642(18) . ?
C9 O3 1.2279(18) . ?

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
N1 C1 N2 108.30(12) . . ?
C3 C2 C5 130.96(13) . . ?
C3 C2 N2 106.67(11) . . ?
N2 C2 C5 122.37(12) . . ?
C2 C3 C6 130.99(13) . . ?
C2 C3 N1 106.81(11) . . ?
N1 C3 C6 122.16(12) . . ?
N1 C7 C8 112.96(13) . . ?
O2 C9 O1 116.53(13) . . ?
O3 C9 O1 118.12(14) . . ?
O3 C9 O2 125.33(14) . . ?
C1 N1 C3 109.02(11) . . ?
C1 N1 C7 127.00(12) . . ?
C3 N1 C7 123.98(11) . . ?
C1 N2 C2 109.20(11) . . ?
C1 N2 C4 124.67(12) . . ?
C2 N2 C4 126.13(11) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 5 3 0.0737 0.0052 4.9981 2.9976 0.5127 -0.7829 0.3117
0 -5 -3 0.0737 -0.0052 -4.9981 -2.9976 -0.5127 0.7829 -0.3117
2 -4 -3 0.0594 1.9972 -3.9978 -2.9983 -0.1460 0.9825 -0.0747
0 0 6 0.0718 0.0030 -0.0036 5.9943 0.4241 -0.3796 -0.8302
-1 0 -6 0.0509 -1.0038 0.0034 -5.9939 -0.5773 0.2204 0.7843
4 0 3 0.0843 4.0049 -0.0011 2.9956 0.8251 0.4468 -0.2317
1 4 5 0.0722 1.0063 3.9971 4.9953 0.7472 -0.6316 -0.0645
-3 3 2 0.0361 -2.9993 2.9982 1.9996 -0.1380 -0.9598 0.0218
-3 -3 -5 0.0639 -3.0073 -2.9975 -4.9944 -0.9936 0.1947 0.1182
-1 -4 2 0.0975 -1.0029 -4.0013 1.9981 -0.2524 0.1888 -0.9040
0 3 -4 0.1051 0.0003 3.0023 -3.9959 -0.1023 -0.1028 0.9895
0 -5 -4 0.0543 -0.0057 -4.9975 -3.9967 -0.5834 0.8461 -0.1734
2 -2 4 0.0915 2.0022 -2.0020 3.9952 0.4690 0.3025 -0.7525
1 0 -6 0.0787 0.9979 0.0037 -5.9947 -0.2708 0.5387 0.8760
_database_code_depnum_ccdc_archive 'CCDC 967637'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cs007
_audit_creation_date             2013-05-02
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H15 N2, Cl'
_chemical_formula_sum            'C8 H15 Cl N2'
_chemical_formula_weight         174.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H15 Cl N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.77997(17)
_cell_length_b                   14.4971(4)
_cell_length_c                   9.8785(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.572(3)
_cell_angle_gamma                90.00
_cell_volume                     954.48(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      5.5000
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.3009
_exptl_crystal_size_mid          0.1526
_exptl_crystal_size_min          0.1152
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4198
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         5.48
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -116.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -54.0000 -157.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -71.00  -31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -54.0000 -157.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   61.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000   22.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   75.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000 -166.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   82.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  157.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  120.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  157.0000 44

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000 -166.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega -125.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega  -60.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   54.0000  166.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega -113.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega -122.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega  -56.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   54.0000  -22.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega   71.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  150.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 19 omega  106.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  -13.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2163932000
_diffrn_orient_matrix_UB_12      0.0054178000
_diffrn_orient_matrix_UB_13      0.0273276000
_diffrn_orient_matrix_UB_21      -0.0689612000
_diffrn_orient_matrix_UB_22      -0.0684779000
_diffrn_orient_matrix_UB_23      -0.1186976000
_diffrn_orient_matrix_UB_31      0.0437572000
_diffrn_orient_matrix_UB_32      -0.0810651000
_diffrn_orient_matrix_UB_33      0.1014973000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1593
_reflns_number_total             1807
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0284(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0628P)²+0.0806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1064
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates and stretchable bonds:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates and stretchable bonds:
 C1(H1)
2.c Idealised Me refined as rotating group with stretchable bonds:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
C1 C 0.4191(2) 0.79155(10) 0.39588(15) 0.0422(4) Uani 1 1 d . . .
H1 H 0.5104(17) 0.8165(5) 0.3456(10) 0.051 Uiso 1 1 calc R . .
C2 C 0.1770(2) 0.77823(11) 0.51735(15) 0.0432(4) Uani 1 1 d . . .
C3 C 0.2502(2) 0.69251(11) 0.50168(15) 0.0425(4) Uani 1 1 d . . .
C4 C 0.2553(3) 0.93847(12) 0.43787(19) 0.0542(4) Uani 1 1 d . . .
H4A H 0.3559(16) 0.9647(4) 0.3923(13) 0.081 Uiso 1 1 calc R . .
H4B H 0.2664(19) 0.9651(4) 0.5281(10) 0.081 Uiso 1 1 calc R . .
H4C H 0.1244(17) 0.9512(2) 0.3850(13) 0.081 Uiso 1 1 calc R . .
C5 C 0.0168(3) 0.81004(14) 0.59076(18) 0.0587(5) Uani 1 1 d . . .
H5A H 0.0721(8) 0.8537(9) 0.6611(13) 0.088 Uiso 1 1 calc R . .
H5B H -0.0369(16) 0.7579(6) 0.6326(13) 0.088 Uiso 1 1 calc R . .
H5C H -0.0888(16) 0.8391(10) 0.5262(8) 0.088 Uiso 1 1 calc R . .
C6 C 0.1954(3) 0.60064(12) 0.5499(2) 0.0570(5) Uani 1 1 d . . .
H6A H 0.161(2) 0.5608(6) 0.4738(10) 0.085 Uiso 1 1 calc R . .
H6B H 0.085(2) 0.60687(19) 0.5952(14) 0.085 Uiso 1 1 calc R . .
H6C H 0.3055(15) 0.5759(5) 0.6115(14) 0.085 Uiso 1 1 calc R . .
C7 C 0.5272(2) 0.62652(12) 0.39024(17) 0.0520(4) Uani 1 1 d . . .
H7A H 0.4386(12) 0.5766(7) 0.3450(6) 0.062 Uiso 1 1 calc R . .
H7B H 0.6071(11) 0.6011(4) 0.4766(11) 0.062 Uiso 1 1 calc R . .
C8 C 0.6659(3) 0.65522(14) 0.2974(2) 0.0621(5) Uani 1 1 d . . .
H8A H 0.5877(10) 0.6794(10) 0.2111(12) 0.093 Uiso 1 1 calc R . .
H8B H 0.7449(17) 0.6018(7) 0.2773(13) 0.093 Uiso 1 1 calc R . .
H8C H 0.757(2) 0.7034(9) 0.3426(9) 0.093 Uiso 1 1 calc R . .
Cl1 Cl 0.25207(5) 0.41822(3) 0.25114(4) 0.0541(2) Uani 1 1 d . . .
N1 N 0.40181(17) 0.70289(9) 0.42499(12) 0.0406(3) Uani 1 1 d . . .
N2 N 0.28465(17) 0.83893(9) 0.45022(12) 0.0418(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0393(7) 0.0449(8) 0.0447(8) 0.0014(6) 0.0138(6) -0.0023(6)
C2 0.0388(7) 0.0520(9) 0.0406(7) 0.0002(6) 0.0121(6) 0.0005(6)
C3 0.0393(7) 0.0495(9) 0.0414(7) 0.0026(6) 0.0141(6) -0.0008(6)
C4 0.0530(9) 0.0418(9) 0.0673(11) -0.0031(7) 0.0097(8) 0.0012(7)
C5 0.0519(9) 0.0701(12) 0.0599(10) -0.0010(8) 0.0254(8) 0.0088(8)
C6 0.0573(10) 0.0536(11) 0.0659(11) 0.0099(8) 0.0269(8) -0.0027(8)
C7 0.0558(9) 0.0461(9) 0.0586(9) -0.0007(7) 0.0228(7) 0.0066(7)
C8 0.0619(10) 0.0586(11) 0.0741(12) -0.0070(9) 0.0347(9) 0.0037(8)
Cl1 0.0496(3) 0.0604(3) 0.0540(3) -0.00473(16) 0.01394(19) 0.00331(16)
N1 0.0393(6) 0.0424(7) 0.0428(6) 0.0009(5) 0.0144(5) 0.0002(5)
N2 0.0395(6) 0.0418(7) 0.0452(7) -0.0011(5) 0.0107(5) 0.0006(5)

_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
C1 N1 1.3269(19) . ?
C1 N2 1.3305(18) . ?
C2 C3 1.358(2) . ?
C2 C5 1.486(2) . ?
C2 N2 1.3873(18) . ?
C3 C6 1.485(2) . ?
C3 N1 1.3923(17) . ?
C4 N2 1.459(2) . ?
C7 C8 1.488(2) . ?
C7 N1 1.4740(19) . ?

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
N1 C1 N2 108.57(12) . . ?
C3 C2 C5 130.94(15) . . ?
C3 C2 N2 106.89(12) . . ?
N2 C2 C5 122.17(15) . . ?
C2 C3 C6 131.77(13) . . ?
C2 C3 N1 106.56(13) . . ?
N1 C3 C6 121.67(14) . . ?
N1 C7 C8 112.96(14) . . ?
C1 N1 C3 109.02(12) . . ?
C1 N1 C7 126.83(12) . . ?
C3 N1 C7 124.07(13) . . ?
C1 N2 C2 108.96(13) . . ?
C1 N2 C4 124.74(13) . . ?
C2 N2 C4 126.29(13) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 -2 -5 0.0514 -2.0000 -2.0000 -5.0000 0.2853 0.8684 -0.4329
2 2 5 0.0638 2.0000 2.0000 5.0000 -0.2853 -0.8684 0.4329
4 4 -3 0.1122 4.0000 4.0000 -3.0000 -0.9259 -0.1937 -0.4537
-4 3 0 0.1063 -4.0000 3.0000 0.0000 0.8818 0.0704 -0.4182
1 -6 5 0.0701 1.0000 -6.0000 5.0000 -0.1123 -0.2516 1.0376
-2 8 -1 0.0455 -2.0000 8.0000 -1.0000 0.4488 -0.2912 -0.8375
0 -7 4 0.0869 -0.0000 -7.0000 4.0000 0.0714 0.0046 0.9734
-1 -3 6 0.1141 -1.0000 -3.0000 6.0000 0.3641 -0.4378 0.8084
-1 -9 -1 0.0617 -1.0000 -9.0000 -1.0000 0.1403 0.8040 0.5843
3 -4 2 0.0928 3.0000 -4.0000 2.0000 -0.6162 -0.1704 0.6585
1 1 -6 0.1161 1.0000 1.0000 -6.0000 -0.3749 0.5747 -0.6463
2 -8 -2 0.0964 2.0000 -8.0000 -2.0000 -0.5308 0.6473 0.5330
0 9 -1 0.0756 0.0000 9.0000 -1.0000 0.0214 -0.4976 -0.8311
1 9 2 0.0638 1.0000 9.0000 2.0000 -0.1130 -0.9227 -0.4828
_database_code_depnum_ccdc_archive 'CCDC 967638'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cs012
_audit_creation_date             2013-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H17 N2, Cl'
_chemical_formula_sum            'C9 H17 Cl N2'
_chemical_formula_weight         188.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H17 Cl N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   19.8873(6)
_cell_length_b                   19.8873(6)
_cell_length_c                   14.4048(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4933.9(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9070
_cell_measurement_theta_min      3.9070
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.1503
_exptl_crystal_size_mid          0.0995
_exptl_crystal_size_min          0.0722
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10529
_diffrn_reflns_theta_full        74.44
_diffrn_reflns_theta_max         74.44
_diffrn_reflns_theta_min         4.00
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9881
_diffrn_measured_fraction_theta_max 0.9881
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -20.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  131.0000 -147.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega  119.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  102.0000  138.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega   71.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -63.0000 -160.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega -126.00 -101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega -117.00  -83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega -126.00  -90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega   47.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   33.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -37.0000 -168.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega -116.00  -67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega -116.00  -14.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
 12 omega   56.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   15.0000   30.0000 122

#__ type_ start__ end____ width___ exp.time_
 13 omega   26.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
 14 omega   56.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   15.0000  150.0000 122

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000 -120.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0054025000
_diffrn_orient_matrix_UB_12      -0.0023840000
_diffrn_orient_matrix_UB_13      0.1067357000
_diffrn_orient_matrix_UB_21      -0.0852719000
_diffrn_orient_matrix_UB_22      -0.0655568000
_diffrn_orient_matrix_UB_23      -0.0060674000
_diffrn_orient_matrix_UB_31      0.0264204000
_diffrn_orient_matrix_UB_32      -0.0608076000
_diffrn_orient_matrix_UB_33      0.0023090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1794
_reflns_number_total             2230
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+3.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0981
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates and stretchable bonds:
 C8(H8A,H8B)
2.b Idealised Me refined as rotating group with stretchable bonds:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,
 H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C1 C 0.56350(11) 0.75455(11) 0.34408(12) 0.0225(4) Uani 1 1 d . . .
C2 C 0.56652(9) 0.66589(10) 0.43517(11) 0.0182(3) Uani 1 1 d . . .
C3 C 0.54940(10) 0.71080(10) 0.48956(12) 0.0201(4) Uani 1 1 d . . .
C4 C 0.56703(13) 0.80095(13) 0.26106(14) 0.0335(5) Uani 1 1 d . . .
H4A H 0.5175(7) 0.7750(6) 0.2288(8) 0.050 Uiso 1 1 calc R . .
H4B H 0.6078(8) 0.8058(8) 0.2196(7) 0.050 Uiso 1 1 calc R . .
H4C H 0.5781(9) 0.8523(7) 0.2806(3) 0.050 Uiso 1 1 calc R . .
C5 C 0.59500(11) 0.65987(11) 0.26649(12) 0.0248(4) Uani 1 1 d . . .
H5A H 0.6435(7) 0.6617(7) 0.2787(5) 0.037 Uiso 1 1 calc R . .
H5B H 0.5998(8) 0.6890(6) 0.2110(7) 0.037 Uiso 1 1 calc R . .
H5C H 0.5547(6) 0.6067(7) 0.2581(6) 0.037 Uiso 1 1 calc R . .
C6 C 0.57543(11) 0.59790(10) 0.45729(12) 0.0227(4) Uani 1 1 d . . .
H6A H 0.5376(7) 0.5533(6) 0.4226(8) 0.034 Uiso 1 1 calc R . .
H6B H 0.5673(8) 0.5869(5) 0.5230(8) 0.034 Uiso 1 1 calc R . .
H6C H 0.6272(7) 0.6092(3) 0.4407(9) 0.034 Uiso 1 1 calc R . .
C7 C 0.53413(11) 0.70660(11) 0.59114(12) 0.0245(4) Uani 1 1 d . . .
H7A H 0.5712(7) 0.7565(7) 0.6203(4) 0.037 Uiso 1 1 calc R . .
H7B H 0.5404(8) 0.6646(8) 0.6186(4) 0.037 Uiso 1 1 calc R . .
H7C H 0.4806(7) 0.6959(8) 0.60184(19) 0.037 Uiso 1 1 calc R . .
C8 C 0.53167(12) 0.82681(11) 0.46242(13) 0.0281(4) Uani 1 1 d . . .
H8A H 0.5558(4) 0.8705(7) 0.4190(7) 0.034 Uiso 1 1 calc R . .
H8B H 0.5549(4) 0.8457(3) 0.5237(10) 0.034 Uiso 1 1 calc R . .
C9 C 0.44577(15) 0.79791(16) 0.4676(2) 0.0514(7) Uani 1 1 d . . .
H9A H 0.4219(5) 0.7812(11) 0.4033(10) 0.077 Uiso 1 1 calc R . .
H9B H 0.4371(2) 0.8412(8) 0.4914(13) 0.077 Uiso 1 1 calc R . .
H9C H 0.4203(5) 0.7518(10) 0.5118(12) 0.077 Uiso 1 1 calc R . .
Cl1 Cl 0.57414(3) 0.54679(3) 0.70665(3) 0.02735(14) Uani 1 1 d . . .
N1 N 0.54792(9) 0.76589(8) 0.43198(10) 0.0214(3) Uani 1 1 d . . .
N2 N 0.57524(9) 0.69374(9) 0.34527(10) 0.0222(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0250(9) 0.0245(9) 0.0204(8) 0.0018(7) 0.0019(7) 0.0141(8)
C2 0.0168(8) 0.0200(8) 0.0166(7) 0.0008(6) -0.0007(6) 0.0083(7)
C3 0.0169(8) 0.0194(9) 0.0206(8) 0.0007(7) -0.0003(7) 0.0064(7)
C4 0.0474(13) 0.0367(11) 0.0246(9) 0.0063(8) 0.0050(9) 0.0272(10)
C5 0.0315(10) 0.0294(10) 0.0170(8) 0.0004(7) 0.0012(7) 0.0180(8)
C6 0.0255(9) 0.0230(9) 0.0196(8) 0.0009(7) -0.0015(7) 0.0120(8)
C7 0.0259(9) 0.0258(9) 0.0220(8) -0.0005(7) 0.0008(7) 0.0132(8)
C8 0.0386(11) 0.0256(10) 0.0264(9) 0.0003(7) 0.0024(8) 0.0207(9)
C9 0.0459(14) 0.0528(15) 0.0703(17) 0.0064(13) 0.0151(13) 0.0358(13)
Cl1 0.0236(2) 0.0330(3) 0.0207(2) -0.00158(17) -0.00045(17) 0.0106(2)
N1 0.0239(8) 0.0211(7) 0.0210(7) 0.0003(6) 0.0012(6) 0.0127(6)
N2 0.0240(8) 0.0238(8) 0.0198(7) 0.0001(6) 0.0011(6) 0.0127(6)

_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
C1 C4 1.491(2) . ?
C1 N1 1.349(2) . ?
C1 N2 1.341(2) . ?
C2 C3 1.353(2) . ?
C2 C6 1.483(2) . ?
C2 N2 1.385(2) . ?
C3 C7 1.488(2) . ?
C3 N1 1.386(2) . ?
C4 H4A 0.9719 . ?
C4 H4B 0.9719 . ?
C4 H4C 0.9719 . ?
C5 H5A 0.9633 . ?
C5 H5B 0.9633 . ?
C5 H5C 0.9633 . ?
C5 N2 1.470(2) . ?
C6 H6A 0.9673 . ?
C6 H6B 0.9673 . ?
C6 H6C 0.9673 . ?
C7 H7A 0.9870 . ?
C7 H7B 0.9870 . ?
C7 H7C 0.9870 . ?
C8 H8A 0.9799 . ?
C8 H8B 0.9799 . ?
C8 C9 1.508(3) . ?
C8 N1 1.468(2) . ?
C9 H9A 1.0185 . ?
C9 H9B 1.0185 . ?
C9 H9C 1.0185 . ?

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
N1 C1 C4 126.38(17) . . ?
N2 C1 C4 126.35(17) . . ?
N2 C1 N1 107.26(15) . . ?
C3 C2 C6 131.40(16) . . ?
C3 C2 N2 107.45(15) . . ?
N2 C2 C6 121.15(15) . . ?
C2 C3 C7 130.06(16) . . ?
C2 C3 N1 106.67(15) . . ?
N1 C3 C7 123.26(16) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.04(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 C3 109.40(14) . . ?
C1 N1 C8 125.58(16) . . ?
C3 N1 C8 125.02(15) . . ?
C1 N2 C2 109.22(15) . . ?
C1 N2 C5 127.60(15) . . ?
C2 N2 C5 123.18(15) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8 12 3 0.0581 -7.9946 11.9972 3.0033 0.3351 -0.1230 -0.9338
-3 4 -9 0.0786 -2.9819 3.9937 -9.0045 -0.9545 0.0471 -0.3424
12 -5 3 0.0279 11.9936 -5.0051 3.0054 0.2679 -0.7128 0.6282
-12 3 -3 0.0645 -11.9958 3.0072 -3.0063 -0.2632 0.8440 -0.5067
-1 11 2 0.0510 -0.9917 10.9906 2.0058 0.1932 -0.6481 -0.6899
2 -9 7 0.0423 1.9795 -8.9886 7.0005 0.7579 0.3780 0.6150
-5 -1 8 0.0574 -5.0158 -0.9894 8.0013 0.8835 0.4440 -0.0539
-9 -3 2 0.0361 -9.0095 -2.9867 1.9951 0.2687 0.9519 -0.0518
9 3 -2 0.0361 9.0095 2.9867 -1.9951 -0.2687 -0.9519 0.0518
4 -9 -7 0.0430 4.0031 -8.9986 -7.0060 -0.7480 0.2911 0.6368
10 -13 1 0.0378 9.9876 -12.9959 0.9994 0.0837 -0.0058 1.0564
8 -7 7 0.0441 7.9836 -6.9967 7.0045 0.7212 -0.2646 0.6526
1 6 -7 0.0676 1.0183 5.9887 -7.0004 -0.7670 -0.4370 -0.3534
-10 12 -2 0.0601 -9.9871 11.9963 -2.0005 -0.1882 0.0773 -0.9980
7 5 3 0.0378 7.0028 4.9895 3.0076 0.2713 -0.9425 -0.1114

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 20 1 ' '
2 0.333 0.667 0.166 102 23 ' '
3 0.667 0.333 0.333 19 1 ' '
4 0.000 0.000 0.500 102 23 ' '
5 0.333 0.667 0.667 19 1 ' '
6 0.667 0.333 0.833 102 23 ' '
_platon_squeeze_details          ?


_database_code_depnum_ccdc_archive 'CCDC 967639'
