# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         1475

_publ_contact_author_name        'Xi Zhang'

_publ_contact_author_email       xi@mail.tsinghua.edu.cn

_publ_contact_author_address     
;

;
loop_
_publ_author_name
'Xi Zhang'

# Attachment '- exp_346.cif'

data_exp_346
_database_code_depnum_ccdc_archive 'CCDC 890516'
#TrackingRef '- exp_346.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H23 N6, Cl '
_chemical_formula_sum            'C11 H23 Cl N6'
_chemical_formula_weight         274.80

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   4.4289(4)
_cell_length_b                   9.6455(18)
_cell_length_c                   17.6718(18)
_cell_angle_alpha                101.395(8)
_cell_angle_beta                 95.279(8)
_cell_angle_gamma                92.673(7)
_cell_volume                     735.27(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1328
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      26

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro (Oxford, 2011)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4647
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2901
_reflns_number_gt                2228
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford, 2011)'
_computing_cell_refinement       'CrysAlisPro (Oxford, 2011)'
_computing_data_reduction        'CrysAlisPro (Oxford, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0010P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     206
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instructions_details 
;
TITL exp_346 in P-1
CELL 0.71073 4.4289 9.6455 17.6718 101.395 95.279 92.673
ZERR 2.00 0.0004 0.0018 0.0018 0.008 0.008 0.007
LATT 1
SFAC C H N Cl
UNIT 22 46 12 2

OMIT -2 52

EQIV $1 X, 1+Y, Z
EQIV $2 -X, 1-Y, 1-Z

HTAB N3 CL1_$1
HTAB N4 CL1
HTAB N5 CL1_$2
HTAB N6 CL1_$1

L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 10

EXYZ C6 C6'
EADP C6 C6'
EXYZ C9 C9'
EADP C9 C9'

DFIX 1.53 0.01 C9 C10 C10 C11 C9' C10' C10' C11' C6 C7 C6 C7'

WGHT 0.001000 1.500000
FVAR 0.30691 0.45020
CL1 4 0.369843 0.133756 0.596802 11.00000 0.02432 0.00908 =
0.05056 0.01094 0.00330 0.00058
N1 3 0.736061 0.695924 0.670733 11.00000 0.01750 0.01364 =
0.02198 0.00301 0.00172 -0.00298
N2 3 0.334140 0.568203 0.577309 11.00000 0.01934 0.00817 =
0.02322 0.00511 0.00037 -0.00088
N3 3 0.454247 0.810669 0.585183 11.00000 0.01899 0.00595 =
0.03335 0.00614 -0.00050 -0.00064
H3A 2 0.404079 0.879230 0.572985 11.00000 -1.20000
N4 3 0.621863 0.457897 0.658766 11.00000 0.02190 0.01333 =
0.02594 0.00843 -0.00403 -0.00285
H4C 2 0.536237 0.392178 0.636303 11.00000 -1.20000
N5 3 0.059223 0.692319 0.499369 11.00000 0.02244 0.00849 =
0.03079 0.00709 -0.00390 0.00081
H5C 2 -0.027097 0.620477 0.475605 11.00000 -1.20000
H5D 2 0.011539 0.766802 0.483490 11.00000 -1.20000
N6 3 0.843247 0.932623 0.671973 11.00000 0.02273 0.01389 =
0.03501 0.00293 0.00450 -0.00540
H6C 2 0.799931 0.995510 0.654118 11.00000 -1.20000
C1 1 0.562761 0.577275 0.634752 11.00000 0.01629 0.01469 =
0.02091 0.00565 0.00580 -0.00122
C2 1 0.281256 0.688419 0.553263 11.00000 0.01351 0.01101 =
0.02243 0.00281 0.00420 0.00063
C3 1 0.678207 0.811225 0.642953 11.00000 0.01578 0.01402 =
0.02673 0.00169 0.00660 -0.00112
C4 1 0.865542 0.440509 0.716428 11.00000 0.02004 0.03001 =
0.03544 0.01770 -0.00678 -0.00478
AFIX 23
H4A 2 1.025841 0.514080 0.719564 11.00000 -1.20000
H4B 2 0.949915 0.349740 0.699921 11.00000 -1.20000
AFIX 0
C5 1 0.759981 0.447657 0.796142 11.00000 0.03079 0.08629 =
0.03746 0.03956 -0.01104 -0.01855
AFIX 23
H5A 2 0.586157 0.380333 0.791284 11.00000 -1.20000
H5B 2 0.920973 0.417265 0.828943 11.00000 -1.20000
AFIX 0
PART 1
C6 1 0.672917 0.590269 0.836577 10.50000 0.03493 0.11299 =
0.02313 0.00914 0.00279 -0.00889
AFIX 3
H6A 2 0.506737 0.619849 0.805087 10.50000 -1.20000
H6B 2 0.844347 0.658720 0.840887 10.50000 -1.20000
AFIX 0
C7 1 0.585124 0.552074 0.913192 10.50000 0.04985 0.05759 =
0.02647 -0.00338 0.00572 -0.01619
AFIX 33
H7A 2 0.523552 0.635058 0.946273 10.50000 -1.50000
H7B 2 0.757063 0.517074 0.938927 10.50000 -1.50000
H7C 2 0.420360 0.480424 0.901846 10.50000 -1.50000
AFIX 0
PART 2
C6' 1 0.672917 0.590269 0.836577 10.50000 0.03493 0.11299 =
0.02313 0.00914 0.00279 -0.00889
AFIX 3
H6D 2 0.507894 0.617914 0.801692 10.50000 -1.20000
H6E 2 0.838903 0.655624 0.836732 10.50000 -1.20000
AFIX 0
C7' 1 0.573128 0.625312 0.919351 10.50000 0.05323 0.03428 =
0.02207 -0.00387 -0.00071 -0.00993
AFIX 33
H7D 2 0.531648 0.723553 0.931940 10.50000 -1.50000
H7E 2 0.732693 0.606528 0.955808 10.50000 -1.50000
H7F 2 0.393034 0.567632 0.921741 10.50000 -1.50000
AFIX 0
PART 0
C8 1 1.069727 0.949284 0.738083 11.00000 0.03798 0.03657 =
0.02701 0.00090 0.00105 -0.02317
AFIX 23
H8A 2 1.225995 1.020562 0.734039 11.00000 -1.20000
H8B 2 1.164855 0.860510 0.737291 11.00000 -1.20000
AFIX 0
PART 1
C9 1 0.937638 0.992002 0.813483 10.50000 0.06720 0.06319 =
0.03580 -0.00944 0.01731 -0.04692
AFIX 23
H9A 2 0.791548 1.061206 0.806027 10.50000 -1.20000
H9B 2 0.822505 0.909053 0.821554 10.50000 -1.20000
AFIX 0
C10 1 1.121155 1.049375 0.885190 10.50000 0.02750 0.04062 =
0.02878 0.01303 -0.00240 -0.00781
AFIX 23
H10A 2 1.254366 1.126115 0.876460 10.50000 -1.20000
H10B 2 1.249363 0.976190 0.897268 10.50000 -1.20000
AFIX 0
C11 1 0.962161 1.105046 0.956246 10.50000 0.04749 0.05663 =
0.03391 0.00914 0.00100 0.00638
AFIX 33
H11A 2 1.110925 1.139434 0.999785 10.50000 -1.50000
H11B 2 0.833917 1.030081 0.967306 10.50000 -1.50000
H11C 2 0.840833 1.180921 0.946699 10.50000 -1.50000
AFIX 0
PART 2
C9' 1 0.937638 0.992002 0.813483 10.50000 0.06720 0.06319 =
0.03580 -0.00944 0.01731 -0.04692
AFIX 23
H9C 2 0.747314 0.936202 0.810418 10.50000 -1.20000
H9D 2 1.074314 0.966324 0.853847 10.50000 -1.20000
AFIX 0
C10' 1 0.881750 1.135129 0.836940 10.50000 0.03205 0.01567 =
0.03133 -0.00055 0.00915 -0.00422
AFIX 23
H10C 2 0.727078 1.159350 0.800089 10.50000 -1.20000
H10D 2 1.065990 1.192734 0.835692 10.50000 -1.20000
AFIX 0
C11' 1 0.778418 1.171387 0.917547 10.50000 0.04262 0.02477 =
0.03843 0.00091 0.00690 0.00236
AFIX 33
H11D 2 0.746417 1.270698 0.930244 10.50000 -1.50000
H11E 2 0.931407 1.149030 0.954576 10.50000 -1.50000
H11F 2 0.592005 1.117390 0.918857 10.50000 -1.50000
PART 0

HKLF 4

REM exp_346 in P-1
REM R1 = 0.0772 for 2228 Fo > 4sig(Fo) and 0.1011 for all 2901 data
REM 206 parameters refined using 6 restraints

END
;

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 0.3698(2) 0.13376(10) 0.59680(7) 0.0274(3) Uani 1 1 d . . .
N1 N 0.7361(7) 0.6959(3) 0.67073(19) 0.0179(7) Uani 1 1 d . . .
N2 N 0.3341(7) 0.5682(3) 0.57731(19) 0.0168(7) Uani 1 1 d . . .
N3 N 0.4542(7) 0.8107(3) 0.5852(2) 0.0194(8) Uani 1 1 d . . .
H3A H 0.404(9) 0.879(5) 0.573(2) 0.023 Uiso 1 1 d . . .
N4 N 0.6219(8) 0.4579(4) 0.6588(2) 0.0203(8) Uani 1 1 d . . .
H4C H 0.536(10) 0.392(5) 0.636(3) 0.024 Uiso 1 1 d . . .
N5 N 0.0592(8) 0.6923(4) 0.4994(2) 0.0206(8) Uani 1 1 d . . .
H5C H -0.027(10) 0.620(5) 0.476(2) 0.025 Uiso 1 1 d . . .
H5D H 0.012(9) 0.767(5) 0.483(2) 0.025 Uiso 1 1 d . . .
N6 N 0.8432(8) 0.9326(4) 0.6720(2) 0.0243(8) Uani 1 1 d . D .
H6C H 0.800(10) 0.996(5) 0.654(3) 0.029 Uiso 1 1 d . . .
C1 C 0.5628(8) 0.5773(4) 0.6348(2) 0.0168(8) Uani 1 1 d . . .
C2 C 0.2813(8) 0.6884(4) 0.5533(2) 0.0156(8) Uani 1 1 d . . .
C3 C 0.6782(8) 0.8112(4) 0.6430(2) 0.0190(9) Uani 1 1 d . . .
C4 C 0.8655(9) 0.4405(5) 0.7164(3) 0.0278(10) Uani 1 1 d . B .
H4A H 1.0258 0.5141 0.7196 0.033 Uiso 1 1 calc R . .
H4B H 0.9499 0.3497 0.6999 0.033 Uiso 1 1 calc R . .
C5 C 0.7600(11) 0.4477(7) 0.7961(3) 0.0494(15) Uani 1 1 d . . .
H5A H 0.5862 0.3803 0.7913 0.059 Uiso 1 1 calc R A 1
H5B H 0.9210 0.4173 0.8289 0.059 Uiso 1 1 calc R A 1
C6 C 0.6729(12) 0.5903(8) 0.8366(3) 0.0581(18) Uani 0.50 1 d PD B 1
H6A H 0.5067 0.6198 0.8051 0.070 Uiso 0.50 1 d PR B 1
H6B H 0.8443 0.6587 0.8409 0.070 Uiso 0.50 1 d PR B 1
C7 C 0.585(4) 0.5521(14) 0.9132(6) 0.047(4) Uani 0.50 1 d PD B 1
H7A H 0.5236 0.6351 0.9463 0.070 Uiso 0.50 1 calc PR B 1
H7B H 0.7571 0.5171 0.9389 0.070 Uiso 0.50 1 calc PR B 1
H7C H 0.4204 0.4804 0.9018 0.070 Uiso 0.50 1 calc PR B 1
C6' C 0.6729(12) 0.5903(8) 0.8366(3) 0.0581(18) Uani 0.50 1 d P B 2
H6D H 0.5079 0.6179 0.8017 0.070 Uiso 0.50 1 d PR B 2
H6E H 0.8389 0.6556 0.8367 0.070 Uiso 0.50 1 d PR B 2
C7' C 0.573(4) 0.6253(12) 0.9194(5) 0.039(3) Uani 0.50 1 d PD B 2
H7D H 0.5316 0.7236 0.9319 0.058 Uiso 0.50 1 calc PR B 2
H7E H 0.7327 0.6065 0.9558 0.058 Uiso 0.50 1 calc PR B 2
H7F H 0.3930 0.5676 0.9217 0.058 Uiso 0.50 1 calc PR B 2
C8 C 1.0697(10) 0.9493(5) 0.7381(3) 0.0356(12) Uani 1 1 d . . .
H8A H 1.2260 1.0206 0.7340 0.043 Uiso 1 1 calc R C 1
H8B H 1.1649 0.8605 0.7373 0.043 Uiso 1 1 calc R C 1
C9 C 0.9376(13) 0.9920(6) 0.8135(3) 0.0590(19) Uani 0.50 1 d PD D 1
H9A H 0.7915 1.0612 0.8060 0.071 Uiso 0.50 1 calc PR D 1
H9B H 0.8225 0.9091 0.8216 0.071 Uiso 0.50 1 calc PR D 1
C10 C 1.1212(18) 1.0494(10) 0.8852(4) 0.032(2) Uani 0.50 1 d PD D 1
H10A H 1.2544 1.1261 0.8765 0.039 Uiso 0.50 1 calc PR D 1
H10B H 1.2494 0.9762 0.8973 0.039 Uiso 0.50 1 calc PR D 1
C11 C 0.962(2) 1.1050(12) 0.9562(5) 0.046(3) Uani 0.50 1 d PD D 1
H11A H 1.1109 1.1394 0.9998 0.069 Uiso 0.50 1 calc PR D 1
H11B H 0.8339 1.0301 0.9673 0.069 Uiso 0.50 1 calc PR D 1
H11C H 0.8408 1.1809 0.9467 0.069 Uiso 0.50 1 calc PR D 1
C9' C 0.9376(13) 0.9920(6) 0.8135(3) 0.0590(19) Uani 0.50 1 d PD D 2
H9C H 0.7473 0.9362 0.8104 0.071 Uiso 0.50 1 calc PR D 2
H9D H 1.0743 0.9663 0.8538 0.071 Uiso 0.50 1 calc PR D 2
C10' C 0.882(2) 1.1351(7) 0.8369(4) 0.027(2) Uani 0.50 1 d PD D 2
H10C H 0.7271 1.1593 0.8001 0.032 Uiso 0.50 1 calc PR D 2
H10D H 1.0660 1.1927 0.8357 0.032 Uiso 0.50 1 calc PR D 2
C11' C 0.778(2) 1.1714(10) 0.9175(5) 0.036(2) Uani 0.50 1 d PD D 2
H11D H 0.7464 1.2707 0.9302 0.054 Uiso 0.50 1 calc PR D 2
H11E H 0.9314 1.1490 0.9546 0.054 Uiso 0.50 1 calc PR D 2
H11F H 0.5920 1.1174 0.9189 0.054 Uiso 0.50 1 calc PR D 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0243(5) 0.0091(5) 0.0506(7) 0.0109(4) 0.0033(5) 0.0006(4)
N1 0.0175(16) 0.0136(17) 0.0220(18) 0.0030(14) 0.0017(14) -0.0030(13)
N2 0.0193(16) 0.0082(15) 0.0232(18) 0.0051(13) 0.0004(14) -0.0009(13)
N3 0.0190(17) 0.0060(16) 0.033(2) 0.0061(14) -0.0005(15) -0.0006(13)
N4 0.0219(18) 0.0133(18) 0.026(2) 0.0084(15) -0.0040(15) -0.0028(14)
N5 0.0224(19) 0.0085(17) 0.031(2) 0.0071(15) -0.0039(16) 0.0008(14)
N6 0.0227(19) 0.0139(18) 0.035(2) 0.0029(16) 0.0045(17) -0.0054(15)
C1 0.0163(19) 0.015(2) 0.021(2) 0.0056(16) 0.0058(17) -0.0012(15)
C2 0.0135(18) 0.0110(19) 0.022(2) 0.0028(16) 0.0042(17) 0.0006(14)
C3 0.016(2) 0.014(2) 0.027(2) 0.0017(16) 0.0066(18) -0.0011(15)
C4 0.020(2) 0.030(2) 0.035(3) 0.018(2) -0.0068(19) -0.0048(18)
C5 0.031(3) 0.086(5) 0.037(3) 0.040(3) -0.011(2) -0.019(3)
C6 0.035(3) 0.113(6) 0.023(3) 0.009(3) 0.003(2) -0.009(3)
C7 0.050(7) 0.058(9) 0.026(6) -0.003(7) 0.006(5) -0.016(8)
C6' 0.035(3) 0.113(6) 0.023(3) 0.009(3) 0.003(2) -0.009(3)
C7' 0.053(7) 0.034(7) 0.022(6) -0.004(5) -0.001(5) -0.010(7)
C8 0.038(3) 0.037(3) 0.027(3) 0.001(2) 0.001(2) -0.023(2)
C9 0.067(4) 0.063(4) 0.036(3) -0.009(3) 0.017(3) -0.047(3)
C10 0.028(5) 0.041(6) 0.029(5) 0.013(4) -0.002(4) -0.008(4)
C11 0.047(6) 0.057(7) 0.034(6) 0.009(5) 0.001(5) 0.006(5)
C9' 0.067(4) 0.063(4) 0.036(3) -0.009(3) 0.017(3) -0.047(3)
C10' 0.032(5) 0.016(4) 0.031(5) -0.001(4) 0.009(4) -0.004(4)
C11' 0.043(6) 0.025(5) 0.038(6) 0.001(4) 0.007(5) 0.002(4)

_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 1.328(5) . ?
N1 C1 1.358(5) . ?
N2 C2 1.335(5) . ?
N2 C1 1.353(5) . ?
N3 C3 1.355(5) . ?
N3 C2 1.367(5) . ?
N3 H3A 0.77(4) . ?
N4 C1 1.332(5) . ?
N4 C4 1.454(5) . ?
N4 H4C 0.74(4) . ?
N5 C2 1.312(5) . ?
N5 H5C 0.80(4) . ?
N5 H5D 0.85(5) . ?
N6 C3 1.335(5) . ?
N6 C8 1.446(6) . ?
N6 H6C 0.76(5) . ?
C4 C5 1.514(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.504(8) . ?
C5 C6' 1.504(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.549(9) . ?
C6 C7' 1.545(9) . ?
C6 H6A 0.9694 . ?
C6 H6B 0.9700 . ?
C6 H6D 0.9927 . ?
C6 H6E 0.9453 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7' H7D 0.9600 . ?
C7' H7E 0.9600 . ?
C7' H7F 0.9600 . ?
C8 C9 1.495(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.437(7) . ?
C9 C10' 1.401(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 H9D 0.9700 . ?
C10 C11 1.514(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10' C11' 1.516(8) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 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
C3 N1 C1 114.9(3) . . ?
C2 N2 C1 115.7(3) . . ?
C3 N3 C2 120.0(3) . . ?
C3 N3 H3A 122(3) . . ?
C2 N3 H3A 117(3) . . ?
C1 N4 C4 126.3(3) . . ?
C1 N4 H4C 116(4) . . ?
C4 N4 H4C 117(4) . . ?
C2 N5 H5C 120(3) . . ?
C2 N5 H5D 124(3) . . ?
H5C N5 H5D 115(4) . . ?
C3 N6 C8 122.9(4) . . ?
C3 N6 H6C 116(4) . . ?
C8 N6 H6C 121(4) . . ?
N4 C1 N2 116.6(3) . . ?
N4 C1 N1 116.8(4) . . ?
N2 C1 N1 126.5(3) . . ?
N5 C2 N2 120.7(3) . . ?
N5 C2 N3 118.6(4) . . ?
N2 C2 N3 120.7(4) . . ?
N1 C3 N6 120.0(4) . . ?
N1 C3 N3 122.1(3) . . ?
N6 C3 N3 118.0(4) . . ?
N4 C4 C5 112.7(4) . . ?
N4 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N4 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 116.1(4) . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 C7 99.5(7) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 114.6 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 116.6 . . ?
H6A C6 H6B 107.8 . . ?
C5 C6 C7' 125.5(7) . . ?
C7' C6 H6D 106.4 . . ?
C7' C6 H6E 105.4 . . ?
C5 C6 H6D 106.2 . . ?
C5 C6 H6E 106.8 . . ?
H6D C6 H6E 104.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7' H7E 109.5 . . ?
C6 C7' H7D 109.5 . . ?
C6 C7' H7F 109.5 . . ?
H7D C7' H7E 109.5 . . ?
H7D C7' H7F 109.5 . . ?
H7E C7' H7F 109.5 . . ?
N6 C8 C9 112.4(4) . . ?
N6 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N6 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 122.7(5) . . ?
C10 C9 H9A 106.7 . . ?
C8 C9 H9A 106.7 . . ?
C10 C9 H9B 106.7 . . ?
C8 C9 H9B 106.7 . . ?
H9A C9 H9B 106.6 . . ?
C10' C9 C8 117.4(5) . . ?
C8 C9 H9C 108.0 . . ?
C8 C9 H9D 108.0 . . ?
C10' C9 H9C 108.0 . . ?
C10' C9 H9D 108.0 . . ?
H9C C9 H9D 107.2 . . ?
C9 C10 C11 118.3(7) . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9' C10' C11' 113.7(7) . . ?
C9' C10' H10C 108.8 . . ?
C9' C10' H10D 108.8 . . ?
C11' C10' H10C 108.8 . . ?
C11' C10' H10D 108.8 . . ?
H10C C10' H10D 107.7 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A Cl1 0.77(4) 2.42(4) 3.125(3) 152(4) 1_565
N4 H4C Cl1 0.74(4) 2.51(4) 3.212(4) 159(5) .
N5 H5D Cl1 0.85(5) 2.46(4) 3.185(4) 144(4) 2_566
N6 H6C Cl1 0.76(5) 2.62(5) 3.288(4) 148(4) 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.082