# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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_apx1704

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H15 B F3 N3 O3 S'
_chemical_formula_weight         289.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1663(9)
_cell_length_b                   9.5042(10)
_cell_length_c                   9.8518(11)
_cell_angle_alpha                109.251(1)
_cell_angle_beta                 93.241(1)
_cell_angle_gamma                115.054(1)
_cell_volume                     636.53(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2921
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.40
_reflns_number_total             2921
_reflns_number_gt                2687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0397P)²+0.3840P] 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         2921
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
S1 S 0.45411(4) 0.27387(4) 0.27778(3) 0.01558(10) Uani 1 1 d . . .
F1 F 0.22784(17) -0.04688(12) 0.12005(11) 0.0444(3) Uani 1 1 d . . .
F2 F 0.17243(13) 0.12632(13) 0.05335(12) 0.0384(3) Uani 1 1 d . . .
F3 F 0.40111(15) 0.08346(12) 0.00050(10) 0.0333(2) Uani 1 1 d . . .
O1 O 0.57733(15) 0.21904(13) 0.32684(11) 0.0251(2) Uani 1 1 d . . .
O2 O 0.32586(16) 0.28867(14) 0.36826(12) 0.0274(2) Uani 1 1 d . . .
O3 O 0.53997(14) 0.41008(12) 0.22839(11) 0.0217(2) Uani 1 1 d . . .
N1 N 0.20011(15) 0.23280(14) 0.62716(12) 0.0158(2) Uani 1 1 d . . .
H1F H 0.1993 0.1829 0.5318 0.019 Uiso 1 1 calc R . .
H1G H 0.2865 0.3418 0.6599 0.019 Uiso 1 1 calc R . .
N2 N 0.59827(15) 0.30598(14) 0.75405(12) 0.0170(2) Uani 1 1 d . . .
N3 N 0.84906(16) 0.52631(15) 0.77500(12) 0.0178(2) Uani 1 1 d . . .
B1 B 0.0008(2) 0.2240(2) 0.63688(17) 0.0187(3) Uani 1 1 d . . .
H1A H -0.0905 0.1092 0.6122 0.028 Uiso 1 1 calc R . .
H1B H -0.0322 0.2655 0.5688 0.028 Uiso 1 1 calc R . .
H1C H 0.0060 0.2921 0.7355 0.028 Uiso 1 1 calc R . .
C1 C 0.25406(19) 0.15174(17) 0.71265(15) 0.0185(3) Uani 1 1 d . . .
H1D H 0.1538 0.0386 0.6864 0.022 Uiso 1 1 calc R . .
H1E H 0.2710 0.2146 0.8169 0.022 Uiso 1 1 calc R . .
C2 C 0.43114(19) 0.14150(17) 0.68706(16) 0.0202(3) Uani 1 1 d . . .
H2A H 0.4432 0.0654 0.7278 0.024 Uiso 1 1 calc R . .
H2B H 0.4219 0.0945 0.5816 0.024 Uiso 1 1 calc R . .
C3 C 0.70717(18) 0.38538(17) 0.67956(14) 0.0175(3) Uani 1 1 d . . .
H3 H 0.6870 0.3480 0.5772 0.021 Uiso 1 1 calc R . .
C4 C 0.67432(19) 0.40053(18) 0.90349(15) 0.0197(3) Uani 1 1 d . . .
H4 H 0.6266 0.3745 0.9806 0.024 Uiso 1 1 calc R . .
C5 C 0.83120(19) 0.53781(18) 0.91576(15) 0.0195(3) Uani 1 1 d . . .
H5 H 0.9123 0.6243 1.0033 0.023 Uiso 1 1 calc R . .
C6 C 1.0067(2) 0.6414(2) 0.73652(17) 0.0255(3) Uani 1 1 d . . .
H6A H 1.1098 0.6196 0.7496 0.038 Uiso 1 1 calc R . .
H6B H 1.0411 0.7558 0.7993 0.038 Uiso 1 1 calc R . .
H6C H 0.9727 0.6245 0.6353 0.038 Uiso 1 1 calc R . .
C7 C 0.3058(2) 0.09923(18) 0.10484(16) 0.0234(3) Uani 1 1 d . . .


_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
S1 O2 1.4349(11) . ?
S1 O1 1.4398(10) . ?
S1 O3 1.4454(10) . ?
S1 C7 1.8232(15) . ?
F1 C7 1.3249(16) . ?
F2 C7 1.3307(18) . ?
F3 C7 1.3314(18) . ?
N1 C1 1.4733(16) . ?
N1 B1 1.6038(18) . ?
N1 H1F 0.9000 . ?
N1 H1G 0.9000 . ?
N2 C3 1.3302(17) . ?
N2 C4 1.3829(18) . ?
N2 C2 1.4673(18) . ?
N3 C3 1.3239(18) . ?
N3 C5 1.3757(17) . ?
N3 C6 1.4606(18) . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?
C1 C2 1.5194(19) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 0.9300 . ?
C4 C5 1.349(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
O2 S1 O1 115.17(7) . . ?
O2 S1 O3 114.97(6) . . ?
O1 S1 O3 115.09(6) . . ?
O2 S1 C7 103.73(7) . . ?
O1 S1 C7 104.01(7) . . ?
O3 S1 C7 101.31(6) . . ?
C1 N1 B1 114.09(10) . . ?
C1 N1 H1F 108.7 . . ?
B1 N1 H1F 108.7 . . ?
C1 N1 H1G 108.7 . . ?
B1 N1 H1G 108.7 . . ?
H1F N1 H1G 107.6 . . ?
C3 N2 C4 108.51(11) . . ?
C3 N2 C2 125.08(12) . . ?
C4 N2 C2 126.34(12) . . ?
C3 N3 C5 108.61(12) . . ?
C3 N3 C6 125.32(12) . . ?
C5 N3 C6 125.84(12) . . ?
N1 B1 H1A 109.5 . . ?
N1 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
N1 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?
N1 C1 C2 113.43(11) . . ?
N1 C1 H1D 108.9 . . ?
C2 C1 H1D 108.9 . . ?
N1 C1 H1E 108.9 . . ?
C2 C1 H1E 108.9 . . ?
H1D C1 H1E 107.7 . . ?
N2 C2 C1 112.99(11) . . ?
N2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N3 C3 N2 108.79(12) . . ?
N3 C3 H3 125.6 . . ?
N2 C3 H3 125.6 . . ?
C5 C4 N2 106.67(12) . . ?
C5 C4 H4 126.7 . . ?
N2 C4 H4 126.7 . . ?
C4 C5 N3 107.42(12) . . ?
C4 C5 H5 126.3 . . ?
N3 C5 H5 126.3 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F1 C7 F2 108.70(12) . . ?
F1 C7 F3 107.52(12) . . ?
F2 C7 F3 106.31(12) . . ?
F1 C7 S1 112.18(10) . . ?
F2 C7 S1 110.51(10) . . ?
F3 C7 S1 111.40(10) . . ?

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.050
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 1006599'
#######################################################################
#
#                 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_apx1772

# start Validation Reply Form
_vrf_PLAT029_apx1772             
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.895 Note  
RESPONSE: The relatively small amount of missing data, about 10%, does 
not compromise the main purpose of the structure in the paper, which is 
to establish connectivity.
;
_vrf_PLAT340_apx1772             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0152 Ang.  
RESPONSE: The crystal was twinned and also a poor diffractor.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H25 Cl N3 Si2'
_chemical_formula_weight         302.98

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'
Si Si 0.0817 0.0704 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.954(5)
_cell_length_b                   11.908(7)
_cell_length_c                   18.248(10)
_cell_angle_alpha                108.424(8)
_cell_angle_beta                 99.976(7)
_cell_angle_gamma                93.421(7)
_cell_volume                     1804.4(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6091
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1159
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.77
_reflns_number_total             6091
_reflns_number_gt                3244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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.

 Methyl group C24 was disordered and refined in two one-half occupancy
 positions.  Two lattice chloride anions were each disordered and 
 refined in two one-half occupancy  positions, with site 
 occupancy factors tied to 1.0.  18 temperature factor restraints were
 used to force convergence.
;

_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)+(0.1344P)²+10.3750P] 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         6091
_refine_ls_number_parameters     360
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1061
_refine_ls_wR_factor_ref         0.3351
_refine_ls_wR_factor_gt          0.2971
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5894(3) 0.2367(2) 0.63603(16) 0.0402(7) Uani 1 1 d . . .
Si2 Si 0.4006(3) 0.4505(2) 0.67254(15) 0.0351(6) Uani 1 1 d . . .
Si3 Si 1.1572(3) 0.9354(2) 0.67816(16) 0.0387(7) Uani 1 1 d . . .
Si4 Si 0.9298(3) 0.73180(19) 0.67879(14) 0.0317(6) Uani 1 1 d . . .
N1 N 0.5394(8) 0.3650(5) 0.6998(4) 0.0311(16) Uani 1 1 d . . .
N2 N 0.6325(10) 0.4470(6) 0.9200(5) 0.049(2) Uani 1 1 d . . .
N3 N 0.8010(13) 0.4822(8) 1.0282(5) 0.074(3) Uani 1 1 d . . .
N4 N 1.0776(7) 0.8491(6) 0.7263(4) 0.0307(16) Uani 1 1 d . . .
N5 N 1.0060(9) 0.9209(7) 0.8935(4) 0.044(2) Uani 1 1 d . A .
N6 N 0.7617(12) 0.9222(12) 0.8919(6) 0.087(4) Uani 1 1 d . . .
C1 C 0.6343(12) 0.1260(8) 0.6870(7) 0.061(3) Uani 1 1 d . . .
H1A H 0.7288 0.1544 0.7248 0.091 Uiso 1 1 calc R . .
H1B H 0.6435 0.0511 0.6489 0.091 Uiso 1 1 calc R . .
H1C H 0.5537 0.1154 0.7137 0.091 Uiso 1 1 calc R . .
C2 C 0.7623(12) 0.2758(9) 0.5998(7) 0.065(3) Uani 1 1 d . . .
H2A H 0.7407 0.3326 0.5732 0.098 Uiso 1 1 calc R . .
H2B H 0.7886 0.2052 0.5639 0.098 Uiso 1 1 calc R . .
H2C H 0.8462 0.3097 0.6438 0.098 Uiso 1 1 calc R . .
C3 C 0.4255(12) 0.1626(8) 0.5506(6) 0.053(3) Uani 1 1 d . . .
H3A H 0.3469 0.1262 0.5685 0.080 Uiso 1 1 calc R . .
H3B H 0.4609 0.1026 0.5105 0.080 Uiso 1 1 calc R . .
H3C H 0.3851 0.2211 0.5293 0.080 Uiso 1 1 calc R . .
C4 C 0.4190(12) 0.4722(8) 0.5770(5) 0.048(2) Uani 1 1 d . . .
H4A H 0.5231 0.5007 0.5798 0.072 Uiso 1 1 calc R . .
H4B H 0.3538 0.5294 0.5676 0.072 Uiso 1 1 calc R . .
H4C H 0.3896 0.3976 0.5348 0.072 Uiso 1 1 calc R . .
C5 C 0.2031(11) 0.3804(9) 0.6637(7) 0.055(3) Uani 1 1 d . . .
H5A H 0.1857 0.3026 0.6244 0.082 Uiso 1 1 calc R . .
H5B H 0.1302 0.4292 0.6487 0.082 Uiso 1 1 calc R . .
H5C H 0.1919 0.3734 0.7135 0.082 Uiso 1 1 calc R . .
C6 C 0.4296(12) 0.6032(8) 0.7463(5) 0.050(3) Uani 1 1 d . . .
H6A H 0.4080 0.5991 0.7952 0.075 Uiso 1 1 calc R . .
H6B H 0.3622 0.6520 0.7271 0.075 Uiso 1 1 calc R . .
H6C H 0.5336 0.6374 0.7547 0.075 Uiso 1 1 calc R . .
C7 C 0.6289(11) 0.4099(7) 0.7796(5) 0.042(2) Uani 1 1 d . . .
H7A H 0.6561 0.4951 0.7936 0.050 Uiso 1 1 calc R . .
H7B H 0.7230 0.3735 0.7806 0.050 Uiso 1 1 calc R . .
C8 C 0.5515(13) 0.3876(8) 0.8404(5) 0.051(3) Uani 1 1 d . . .
H8A H 0.4507 0.4135 0.8344 0.061 Uiso 1 1 calc R . .
H8B H 0.5380 0.3025 0.8311 0.061 Uiso 1 1 calc R . .
C9 C 0.6313(13) 0.5631(8) 0.9664(6) 0.054(3) Uani 1 1 d . . .
H9 H 0.5694 0.6166 0.9532 0.065 Uiso 1 1 calc R . .
C10 C 0.7337(13) 0.5864(8) 1.0339(6) 0.052(3) Uani 1 1 d . . .
H10 H 0.7555 0.6577 1.0759 0.063 Uiso 1 1 calc R . .
C11 C 0.7386(15) 0.4046(9) 0.9598(6) 0.071(3) Uani 1 1 d U . .
H11 H 0.7658 0.3280 0.9411 0.085 Uiso 1 1 calc R . .
C12 C 0.920(2) 0.4665(13) 1.0913(7) 0.114(7) Uani 1 1 d . . .
C13 C 1.3087(10) 0.8595(8) 0.6308(6) 0.046(2) Uani 1 1 d . . .
H13A H 1.3773 0.8363 0.6685 0.068 Uiso 1 1 calc R . .
H13B H 1.3642 0.9131 0.6124 0.068 Uiso 1 1 calc R . .
H13C H 1.2625 0.7900 0.5870 0.068 Uiso 1 1 calc R . .
C14 C 1.0092(11) 0.9602(9) 0.6012(6) 0.054(3) Uani 1 1 d . . .
H14A H 0.9663 0.8850 0.5619 0.081 Uiso 1 1 calc R . .
H14B H 1.0552 1.0103 0.5769 0.081 Uiso 1 1 calc R . .
H14C H 0.9299 0.9983 0.6252 0.081 Uiso 1 1 calc R . .
C15 C 1.2403(13) 1.0855(8) 0.7487(7) 0.063(3) Uani 1 1 d . . .
H15A H 1.1610 1.1261 0.7711 0.094 Uiso 1 1 calc R . .
H15B H 1.2860 1.1308 0.7213 0.094 Uiso 1 1 calc R . .
H15C H 1.3166 1.0770 0.7899 0.094 Uiso 1 1 calc R . .
C16 C 0.7419(10) 0.7896(8) 0.6605(5) 0.042(2) Uani 1 1 d . . .
H16A H 0.7193 0.8361 0.7099 0.063 Uiso 1 1 calc R . .
H16B H 0.6631 0.7238 0.6343 0.063 Uiso 1 1 calc R . .
H16C H 0.7471 0.8386 0.6279 0.063 Uiso 1 1 calc R . .
C17 C 0.9667(11) 0.6339(8) 0.5824(5) 0.044(2) Uani 1 1 d . . .
H17A H 0.9595 0.6771 0.5457 0.067 Uiso 1 1 calc R . .
H17B H 0.8923 0.5644 0.5616 0.067 Uiso 1 1 calc R . .
H17C H 1.0672 0.6102 0.5904 0.067 Uiso 1 1 calc R . .
C18 C 0.9099(11) 0.6331(7) 0.7386(5) 0.043(2) Uani 1 1 d . . .
H18A H 1.0023 0.5974 0.7458 0.065 Uiso 1 1 calc R . .
H18B H 0.8259 0.5717 0.7117 0.065 Uiso 1 1 calc R . .
H18C H 0.8914 0.6792 0.7891 0.065 Uiso 1 1 calc R . .
C19 C 1.1775(10) 0.8519(7) 0.8009(5) 0.035(2) Uani 1 1 d . . .
H19A H 1.2831 0.8647 0.7965 0.042 Uiso 1 1 calc R . .
H19B H 1.1613 0.7743 0.8070 0.042 Uiso 1 1 calc R . .
C20 C 1.1532(10) 0.9457(8) 0.8743(5) 0.043(2) Uani 1 1 d . . .
H20A H 1.2342 0.9496 0.9183 0.051 Uiso 1 1 calc R . .
H20B H 1.1592 1.0228 0.8668 0.051 Uiso 1 1 calc R . .
C21 C 0.9721(15) 0.8532(9) 0.9380(6) 0.063(3) Uani 1 1 d . . .
H21 H 1.0381 0.8136 0.9636 0.075 Uiso 1 1 calc R A .
C22 C 0.8162(19) 0.8568(12) 0.9365(8) 0.085(5) Uani 1 1 d . A .
H22 H 0.7589 0.8200 0.9623 0.102 Uiso 1 1 calc R . .
C23 C 0.8761(13) 0.9599(12) 0.8672(6) 0.066(3) Uani 1 1 d . A .
H23 H 0.8692 1.0078 0.8355 0.079 Uiso 1 1 calc R . .
C24 C 0.607(3) 0.977(2) 0.8725(14) 0.058(5) Uani 0.50 1 d PU A 1
C24' C 0.597(3) 0.921(2) 0.8873(14) 0.058(5) Uani 0.50 1 d PU A 2
Cl1 Cl 0.673(3) 0.2513(13) 0.0464(8) 0.043(5) Uani 0.32(3) 1 d P . .
Cl2 Cl 0.0556(7) 0.7835(5) 0.1291(4) 0.058(2) Uani 0.695(18) 1 d P . .
Cl1' Cl 0.581(2) 0.2111(12) 0.0341(4) 0.065(4) Uani 0.68(3) 1 d P . .
Cl2' Cl 0.0203(10) 0.7563(8) 0.1663(9) 0.039(4) Uani 0.305(18) 1 d P . .


_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
Si1 N1 1.740(7) . ?
Si1 C1 1.864(9) . ?
Si1 C2 1.874(10) . ?
Si1 C3 1.883(10) . ?
Si2 N1 1.756(7) . ?
Si2 C6 1.860(9) . ?
Si2 C5 1.869(10) . ?
Si2 C4 1.873(9) . ?
Si3 N4 1.742(7) . ?
Si3 C13 1.860(9) . ?
Si3 C15 1.860(10) . ?
Si3 C14 1.866(10) . ?
Si4 N4 1.753(7) . ?
Si4 C18 1.859(9) . ?
Si4 C16 1.871(9) . ?
Si4 C17 1.875(9) . ?
N1 C7 1.449(11) . ?
N2 C11 1.317(12) . ?
N2 C9 1.376(11) . ?
N2 C8 1.436(12) . ?
N3 C11 1.302(13) . ?
N3 C10 1.394(11) . ?
N3 C12 1.494(13) . ?
N4 C19 1.483(10) . ?
N5 C23 1.345(13) . ?
N5 C21 1.369(14) . ?
N5 C20 1.458(12) . ?
N6 C23 1.298(15) . ?
N6 C22 1.348(18) . ?
N6 C24' 1.46(3) . ?
N6 C24 1.60(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.488(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.340(13) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.508(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.394(18) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
Cl1 Cl1' 0.877(10) . ?
Cl2 Cl2' 0.932(11) . ?

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 Si1 C1 110.9(4) . . ?
N1 Si1 C2 109.6(4) . . ?
C1 Si1 C2 108.6(5) . . ?
N1 Si1 C3 110.4(4) . . ?
C1 Si1 C3 106.8(5) . . ?
C2 Si1 C3 110.5(5) . . ?
N1 Si2 C6 110.5(4) . . ?
N1 Si2 C5 111.6(4) . . ?
C6 Si2 C5 108.8(5) . . ?
N1 Si2 C4 110.9(4) . . ?
C6 Si2 C4 105.4(4) . . ?
C5 Si2 C4 109.5(5) . . ?
N4 Si3 C13 109.8(4) . . ?
N4 Si3 C15 110.7(4) . . ?
C13 Si3 C15 109.6(5) . . ?
N4 Si3 C14 111.1(4) . . ?
C13 Si3 C14 109.1(5) . . ?
C15 Si3 C14 106.5(5) . . ?
N4 Si4 C18 111.7(4) . . ?
N4 Si4 C16 111.1(4) . . ?
C18 Si4 C16 107.4(4) . . ?
N4 Si4 C17 111.4(4) . . ?
C18 Si4 C17 106.1(4) . . ?
C16 Si4 C17 108.9(4) . . ?
C7 N1 Si1 117.0(5) . . ?
C7 N1 Si2 117.8(5) . . ?
Si1 N1 Si2 125.0(4) . . ?
C11 N2 C9 105.8(8) . . ?
C11 N2 C8 125.8(8) . . ?
C9 N2 C8 127.9(8) . . ?
C11 N3 C10 107.0(8) . . ?
C11 N3 C12 128.2(8) . . ?
C10 N3 C12 124.7(9) . . ?
C19 N4 Si3 113.9(5) . . ?
C19 N4 Si4 119.4(5) . . ?
Si3 N4 Si4 123.3(4) . . ?
C23 N5 C21 107.8(10) . . ?
C23 N5 C20 124.5(9) . . ?
C21 N5 C20 127.8(9) . . ?
C23 N6 C22 107.1(12) . . ?
C23 N6 C24' 143.7(17) . . ?
C22 N6 C24' 109.1(16) . . ?
C23 N6 C24 114.8(15) . . ?
C22 N6 C24 137.4(15) . . ?
C24' N6 C24 30.0(11) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si2 C4 H4A 109.5 . . ?
Si2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si2 C5 H5A 109.5 . . ?
Si2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si2 C6 H6A 109.5 . . ?
Si2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 115.0(8) . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N2 C8 C7 114.1(9) . . ?
N2 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 N2 108.9(8) . . ?
C10 C9 H9 125.6 . . ?
N2 C9 H9 125.6 . . ?
C9 C10 N3 106.1(9) . . ?
C9 C10 H10 126.9 . . ?
N3 C10 H10 126.9 . . ?
N3 C11 N2 112.1(8) . . ?
N3 C11 H11 123.9 . . ?
N2 C11 H11 123.9 . . ?
Si3 C13 H13A 109.5 . . ?
Si3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si3 C14 H14A 109.5 . . ?
Si3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si3 C15 H15A 109.5 . . ?
Si3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si4 C16 H16A 109.5 . . ?
Si4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si4 C17 H17A 109.5 . . ?
Si4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si4 C18 H18A 109.5 . . ?
Si4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 115.3(7) . . ?
N4 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
N4 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
N5 C20 C19 112.2(7) . . ?
N5 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
N5 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N5 C21 C22 104.5(12) . . ?
N5 C21 H21 127.8 . . ?
C22 C21 H21 127.8 . . ?
N6 C22 C21 109.3(12) . . ?
N6 C22 H22 125.3 . . ?
C21 C22 H22 125.3 . . ?
N6 C23 N5 111.4(12) . . ?
N6 C23 H23 124.3 . . ?
N5 C23 H23 124.3 . . ?

_diffrn_measured_fraction_theta_max 0.879
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.895
_refine_diff_density_max         0.990
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.116
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 1006600'
#######################################################################
#
#                 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_eimetnh3_2cl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H15 Cl2 N3'
_chemical_formula_weight         212.12

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'

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                   10.2973(11)
_cell_length_b                   13.2211(14)
_cell_length_c                   8.8908(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.7620(10)
_cell_angle_gamma                90.00
_cell_volume                     1116.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8815
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12717
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         28.60
_reflns_number_total             2707
_reflns_number_gt                2321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0266P)²+0.4129P] 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         2707
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.16806(3) 0.13082(2) 0.92560(4) 0.01769(9) Uani 1 1 d . . .
Cl2 Cl 0.25448(3) 0.64394(2) 0.06718(4) 0.01880(9) Uani 1 1 d . . .
N1 N 0.37359(12) 0.13409(8) 0.62383(14) 0.0154(2) Uani 1 1 d . . .
N2 N 0.18592(11) 0.09873(8) 0.41379(13) 0.0147(2) Uani 1 1 d . . .
N3 N -0.08122(12) 0.22754(9) 0.23791(14) 0.0185(2) Uani 1 1 d . . .
H3A H -0.1308 0.2113 0.2972 0.028 Uiso 1 1 calc R . .
H3B H -0.1339 0.2653 0.1534 0.028 Uiso 1 1 calc R . .
H3C H -0.0050 0.2622 0.2992 0.028 Uiso 1 1 calc R . .
C1 C 0.57293(17) 0.06979(14) 0.8616(2) 0.0360(4) Uani 1 1 d . . .
H1A H 0.5245 0.0061 0.8431 0.054 Uiso 1 1 calc R . .
H1B H 0.6233 0.0798 0.9766 0.054 Uiso 1 1 calc R . .
H1C H 0.6381 0.0700 0.8082 0.054 Uiso 1 1 calc R . .
C2 C 0.46722(15) 0.15417(11) 0.79359(17) 0.0216(3) Uani 1 1 d . . .
H2A H 0.4115 0.1612 0.8595 0.026 Uiso 1 1 calc R . .
H2B H 0.5168 0.2173 0.7992 0.026 Uiso 1 1 calc R . .
C3 C 0.23721(14) 0.11371(10) 0.57375(16) 0.0153(3) Uani 1 1 d . . .
H3 H 0.1860 0.1105 0.6398 0.018 Uiso 1 1 calc R . .
C4 C 0.41128(15) 0.13079(10) 0.49114(17) 0.0192(3) Uani 1 1 d . . .
H4 H 0.5009 0.1414 0.4921 0.023 Uiso 1 1 calc R . .
C5 C 0.29355(15) 0.10920(10) 0.35928(17) 0.0194(3) Uani 1 1 d . . .
H5 H 0.2865 0.1027 0.2523 0.023 Uiso 1 1 calc R . .
C6 C 0.04326(14) 0.06335(10) 0.31577(16) 0.0192(3) Uani 1 1 d . . .
H6A H -0.0082 0.0553 0.3862 0.023 Uiso 1 1 calc R . .
H6B H 0.0492 -0.0026 0.2709 0.023 Uiso 1 1 calc R . .
C7 C -0.03793(14) 0.13384(11) 0.17775(16) 0.0195(3) Uani 1 1 d . . .
H7A H 0.0201 0.1516 0.1180 0.023 Uiso 1 1 calc R . .
H7B H -0.1211 0.0993 0.1032 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
N1 C3 1.3264(17) . ?
N1 C4 1.3779(17) . ?
N1 C2 1.4670(17) . ?
N2 C3 1.3264(16) . ?
N2 C5 1.3777(17) . ?
N2 C6 1.4648(16) . ?
N3 C7 1.4845(17) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C1 C2 1.512(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 0.9300 . ?
C4 C5 1.3512(19) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.5098(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C3 N1 C4 108.58(11) . . ?
C3 N1 C2 124.83(11) . . ?
C4 N1 C2 126.57(11) . . ?
C3 N2 C5 108.75(11) . . ?
C3 N2 C6 125.25(11) . . ?
C5 N2 C6 125.51(11) . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 111.27(12) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 N2 108.72(11) . . ?
N1 C3 H3 125.6 . . ?
N2 C3 H3 125.6 . . ?
C5 C4 N1 107.10(12) . . ?
C5 C4 H4 126.4 . . ?
N1 C4 H4 126.4 . . ?
C4 C5 N2 106.85(12) . . ?
C4 C5 H5 126.6 . . ?
N2 C5 H5 126.6 . . ?
N2 C6 C7 113.51(11) . . ?
N2 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N3 C7 C6 111.79(11) . . ?
N3 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?

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
C3 N1 C2 C1 111.65(15) . . . . ?
C4 N1 C2 C1 -66.79(18) . . . . ?
C4 N1 C3 N2 -0.75(15) . . . . ?
C2 N1 C3 N2 -179.43(12) . . . . ?
C5 N2 C3 N1 0.41(15) . . . . ?
C6 N2 C3 N1 172.76(11) . . . . ?
C3 N1 C4 C5 0.80(15) . . . . ?
C2 N1 C4 C5 179.45(12) . . . . ?
N1 C4 C5 N2 -0.54(15) . . . . ?
C3 N2 C5 C4 0.09(15) . . . . ?
C6 N2 C5 C4 -172.23(12) . . . . ?
C3 N2 C6 C7 123.62(14) . . . . ?
C5 N2 C6 C7 -65.30(17) . . . . ?
N2 C6 C7 N3 -72.42(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.051
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 1006601'
