# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_4a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N5, C2 H6 O S'
_chemical_formula_sum            'C21 H25 N5 O S'

_chemical_formula_weight         395.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.5845(3)
_cell_length_b                   10.8223(3)
_cell_length_c                   12.5073(4)
_cell_angle_alpha                84.207(2)
_cell_angle_beta                 72.287(2)
_cell_angle_gamma                75.180(2)
_cell_volume                     1069.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.62

_exptl_crystal_description       'needle shape'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420.0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13065
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.42
_reflns_number_total             5294
_reflns_number_gt                3420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1324P)²+0.7180P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4622
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2513
_refine_ls_wR_factor_gt          0.2353
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.002

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
C9 C 0.6218(3) 0.4809(2) 0.1958(2) 0.0342(5) Uani 1 1 d . . .
C12 C 0.4749(3) 0.6232(2) 0.3869(2) 0.0330(5) Uani 1 1 d . . .
C10 C 0.6976(3) 0.5758(2) 0.2165(2) 0.0356(6) Uani 1 1 d . . .
C11 C 0.6249(3) 0.6459(2) 0.3147(2) 0.0329(5) Uani 1 1 d . . .
N5 N 0.6971(3) 0.4102(2) 0.1034(2) 0.0453(6) Uani 1 1 d . . .
C3 C 0.7040(3) 0.7434(2) 0.3375(2) 0.0349(5) Uani 1 1 d . . .
C1 C 0.3927(3) 0.6875(3) 0.4911(2) 0.0383(6) Uani 1 1 d . . .
C2 C 0.8385(4) 0.6060(3) 0.1321(3) 0.0473(7) Uani 1 1 d . . .
C14 C 0.6442(4) 0.3043(3) 0.0736(2) 0.0454(7) Uani 1 1 d . . .
H14 H 0.5256 0.3114 0.1155 0.054 Uiso 1 1 calc R . .
C4 C 0.6140(4) 0.8693(3) 0.3556(2) 0.0447(7) Uani 1 1 d . . .
H4 H 0.5011 0.8919 0.3575 0.054 Uiso 1 1 calc R . .
C8 C 0.8725(4) 0.7102(3) 0.3372(2) 0.0445(7) Uani 1 1 d . . .
H8 H 0.9342 0.6259 0.3262 0.053 Uiso 1 1 calc R . .
C7 C 0.9476(4) 0.8033(3) 0.3533(3) 0.0564(8) Uani 1 1 d . . .
H7 H 1.0596 0.7813 0.3535 0.068 Uiso 1 1 calc R . .
C5 C 0.6904(4) 0.9620(3) 0.3708(3) 0.0546(8) Uani 1 1 d . . .
H5 H 0.6292 1.0464 0.3822 0.066 Uiso 1 1 calc R . .
C6 C 0.8567(5) 0.9289(3) 0.3691(3) 0.0590(9) Uani 1 1 d . . .
H6 H 0.9082 0.9912 0.3786 0.071 Uiso 1 1 calc R . .
C17 C 0.7125(5) 0.0759(4) -0.0571(4) 0.0744(11) Uani 1 1 d . . .
H17A H 0.8296 0.0667 -0.1002 0.089 Uiso 1 1 calc R . .
H17B H 0.6735 0.0072 -0.0768 0.089 Uiso 1 1 calc R . .
C16 C 0.6113(6) 0.2013(4) -0.0869(4) 0.0774(12) Uani 1 1 d . . .
H16A H 0.6285 0.2070 -0.1674 0.093 Uiso 1 1 calc R . .
H16B H 0.4928 0.2062 -0.0505 0.093 Uiso 1 1 calc R . .
C15 C 0.6594(5) 0.3128(4) -0.0515(3) 0.0617(9) Uani 1 1 d . . .
H15A H 0.5867 0.3922 -0.0682 0.074 Uiso 1 1 calc R . .
H15B H 0.7744 0.3134 -0.0941 0.074 Uiso 1 1 calc R . .
C19 C 0.7452(5) 0.1778(3) 0.1044(3) 0.0645(9) Uani 1 1 d . . .
H19A H 0.7264 0.1723 0.1851 0.077 Uiso 1 1 calc R . .
H19B H 0.8640 0.1730 0.0691 0.077 Uiso 1 1 calc R . .
C18 C 0.6987(7) 0.0648(4) 0.0681(4) 0.0846(13) Uani 1 1 d . . .
H18A H 0.5845 0.0624 0.1111 0.102 Uiso 1 1 calc R . .
H18B H 0.7733 -0.0143 0.0835 0.102 Uiso 1 1 calc R . .
N3 N 0.4748(3) 0.4632(2) 0.26384(17) 0.0351(5) Uani 1 1 d . . .
N4 N 0.2536(3) 0.5141(3) 0.4218(2) 0.0468(6) Uani 1 1 d . . .
N2 N 0.3229(3) 0.7348(3) 0.5752(2) 0.0561(7) Uani 1 1 d . . .
N1 N 0.9481(4) 0.6284(3) 0.0611(3) 0.0730(10) Uani 1 1 d . . .
S1 S 0.07957(12) 0.24245(10) 0.34454(11) 0.0778(4) Uani 1 1 d . . .
C20 C 0.2936(5) 0.1867(4) 0.3329(4) 0.0780(12) Uani 1 1 d . . .
H20A H 0.3540 0.2466 0.2885 0.117 Uiso 1 1 calc R . .
H20B H 0.3351 0.1053 0.2974 0.117 Uiso 1 1 calc R . .
H20C H 0.3093 0.1775 0.4063 0.117 Uiso 1 1 calc R . .
C21 C 0.0956(9) 0.2731(7) 0.2017(5) 0.155(4) Uani 1 1 d . . .
H21A H -0.0144 0.3095 0.1931 0.233 Uiso 1 1 calc R . .
H21B H 0.1439 0.1945 0.1619 0.233 Uiso 1 1 calc R . .
H21C H 0.1661 0.3318 0.1720 0.233 Uiso 1 1 calc R . .
O1 O 0.0266(3) 0.3711(2) 0.3910(2) 0.0625(7) Uani 1 1 d . . .
C22 C 0.4010(3) 0.5328(2) 0.3568(2) 0.0332(5) Uani 1 1 d . . .
H4A H 0.206(4) 0.548(3) 0.476(3) 0.042(8) Uiso 1 1 d . . .
H4B H 0.207(4) 0.468(3) 0.403(3) 0.050(9) Uiso 1 1 d . . .
H5N H 0.788(5) 0.413(3) 0.064(3) 0.049(9) Uiso 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
C9 N3 1.339(3) . ?
C9 N5 1.345(3) . ?
C9 C10 1.430(4) . ?
C12 C11 1.395(3) . ?
C12 C22 1.428(3) . ?
C12 C1 1.432(3) . ?
C10 C11 1.398(3) . ?
C10 C2 1.427(4) . ?
C11 C3 1.483(3) . ?
N5 C14 1.454(4) . ?
C3 C4 1.387(4) . ?
C3 C8 1.397(4) . ?
C1 N2 1.139(3) . ?
C2 N1 1.139(4) . ?
C14 C19 1.504(5) . ?
C14 C15 1.525(4) . ?
C4 C5 1.387(4) . ?
C8 C7 1.387(4) . ?
C7 C6 1.383(5) . ?
C5 C6 1.374(5) . ?
C17 C16 1.492(6) . ?
C17 C18 1.528(6) . ?
C16 C15 1.516(5) . ?
C19 C18 1.527(5) . ?
N3 C22 1.343(3) . ?
N4 C22 1.333(3) . ?
S1 O1 1.470(2) . ?
S1 C20 1.746(4) . ?
S1 C21 1.753(6) . ?

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
N3 C9 N5 118.9(2) . . ?
N3 C9 C10 121.8(2) . . ?
N5 C9 C10 119.3(2) . . ?
C11 C12 C22 119.3(2) . . ?
C11 C12 C1 121.9(2) . . ?
C22 C12 C1 118.9(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 C2 120.4(2) . . ?
C9 C10 C2 119.6(2) . . ?
C10 C11 C12 117.5(2) . . ?
C10 C11 C3 120.2(2) . . ?
C12 C11 C3 122.3(2) . . ?
C9 N5 C14 126.4(2) . . ?
C4 C3 C8 119.1(2) . . ?
C4 C3 C11 120.6(2) . . ?
C8 C3 C11 120.3(2) . . ?
N2 C1 C12 176.9(3) . . ?
N1 C2 C10 176.7(3) . . ?
N5 C14 C19 111.2(3) . . ?
N5 C14 C15 109.7(3) . . ?
C19 C14 C15 110.9(2) . . ?
C5 C4 C3 120.7(3) . . ?
C7 C8 C3 119.8(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C5 C4 119.9(3) . . ?
C5 C6 C7 120.3(3) . . ?
C16 C17 C18 111.6(3) . . ?
C15 C16 C17 111.8(3) . . ?
C16 C15 C14 111.4(3) . . ?
C14 C19 C18 112.3(3) . . ?
C19 C18 C17 110.8(3) . . ?
C22 N3 C9 118.8(2) . . ?
O1 S1 C20 106.94(19) . . ?
O1 S1 C21 103.2(3) . . ?
C20 S1 C21 98.5(3) . . ?
N3 C22 N4 117.2(2) . . ?
N3 C22 C12 122.5(2) . . ?
N4 C22 C12 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.109
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 1006358'
#######################################################################
#
#                 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_platon

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl N5'
_chemical_formula_sum            'C20 H16 Cl N5'
_chemical_formula_weight         361.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   12.968(2)
_cell_length_b                   10.2902(18)
_cell_length_c                   13.385(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.889(12)
_cell_angle_gamma                90.00
_cell_volume                     1764.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            olorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12046
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2962
_reflns_number_gt                1947
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+40.0000P] 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         2962
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1914
_refine_ls_R_factor_gt           0.1537
_refine_ls_wR_factor_ref         0.3821
_refine_ls_wR_factor_gt          0.3668
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.1698(3) 0.2606(4) 0.8726(3) 0.0922(14) Uani 1 1 d . . .
C7 C 0.1887(9) -0.1111(10) 0.5512(9) 0.047(3) Uani 1 1 d . . .
H7A H 0.2032 -0.1291 0.6232 0.056 Uiso 1 1 calc R . .
H7B H 0.1176 -0.1386 0.5276 0.056 Uiso 1 1 calc R . .
N15 N 0.3874(8) 0.3843(10) 0.7123(8) 0.059(3) Uani 1 1 d . . .
N14 N -0.0180(10) 0.3454(12) 0.3409(9) 0.080(4) Uani 1 1 d . . .
N16 N 0.3507(8) 0.0420(10) 0.6522(7) 0.057(3) Uani 1 1 d . . .
H16A H 0.3761 0.0864 0.7051 0.069 Uiso 1 1 d R . .
H16B H 0.3339 -0.0344 0.6711 0.069 Uiso 1 1 d R . .
N13 N 0.0781(8) 0.0246(11) 0.3897(7) 0.060(3) Uani 1 1 d . . .
H13A H 0.0541 -0.0456 0.4124 0.072 Uiso 1 1 d R . .
H13B H 0.0276 0.0682 0.3562 0.072 Uiso 1 1 d R . .
C1 C 0.2594(9) -0.1932(12) 0.5003(9) 0.052(3) Uani 1 1 d . . .
C2 C 0.3189(11) -0.1424(14) 0.4309(11) 0.072(4) Uani 1 1 d . . .
H2 H 0.3186 -0.0540 0.4163 0.087 Uiso 1 1 calc R . .
C3 C 0.3798(13) -0.2314(19) 0.3834(14) 0.093(5) Uani 1 1 d . . .
H3 H 0.4186 -0.1982 0.3363 0.112 Uiso 1 1 calc R . .
C4 C 0.3852(13) -0.3558(19) 0.4009(15) 0.096(5) Uani 1 1 d . . .
H4 H 0.4264 -0.4097 0.3677 0.116 Uiso 1 1 calc R . .
C5 C 0.3283(13) -0.4037(15) 0.4697(13) 0.088(5) Uani 1 1 d . . .
H5 H 0.3320 -0.4921 0.4844 0.105 Uiso 1 1 calc R . .
C6 C 0.2633(10) -0.3237(11) 0.5199(10) 0.060(3) Uani 1 1 d . . .
H6 H 0.2240 -0.3595 0.5655 0.072 Uiso 1 1 calc R . .
C19 C 0.0097(10) 0.2000(13) 0.8083(10) 0.064(3) Uani 1 1 d . . .
H19 H 0.0210 0.1472 0.8653 0.076 Uiso 1 1 calc R . .
C20 C 0.0850(9) 0.2054(11) 0.7402(9) 0.051(3) Uani 1 1 d . . .
H20 H 0.1465 0.1576 0.7533 0.061 Uiso 1 1 calc R . .
C15 C 0.0652(8) 0.2815(11) 0.6564(8) 0.047(3) Uani 1 1 d . . .
C16 C -0.0284(11) 0.3518(13) 0.6396(10) 0.064(4) Uani 1 1 d . . .
H16 H -0.0426 0.4040 0.5824 0.077 Uiso 1 1 calc R . .
C17 C -0.0993(10) 0.3459(14) 0.7052(11) 0.071(4) Uani 1 1 d . . .
H17 H -0.1616 0.3920 0.6921 0.085 Uiso 1 1 calc R . .
C18 C -0.0779(9) 0.2729(11) 0.7882(9) 0.051(3) Uani 1 1 d . . .
C10 C 0.0384(10) 0.2888(12) 0.4038(9) 0.053(3) Uani 1 1 d . . .
C14 C 0.3259(9) 0.3168(11) 0.6703(8) 0.047(3) Uani 1 1 d . . .
C11 C 0.1442(8) 0.2895(10) 0.5785(8) 0.044(3) Uani 1 1 d . . .
H11 H 0.1537 0.3817 0.5640 0.052 Uiso 1 1 calc R . .
C8 C 0.1234(8) 0.0942(11) 0.4663(7) 0.042(3) Uani 1 1 d . . .
C13 C 0.2657(8) 0.1021(11) 0.6052(8) 0.044(3) Uani 1 1 d . . .
C12 C 0.2461(8) 0.2373(11) 0.6181(8) 0.046(3) Uani 1 1 d . . .
C9 C 0.1036(8) 0.2239(11) 0.4794(8) 0.042(2) Uani 1 1 d . . .
N12 N 0.1942(7) 0.0332(8) 0.5372(7) 0.043(2) 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
Cl1 C18 1.768(12) . ?
C7 C1 1.487(15) . ?
C7 N12 1.500(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N15 C14 1.139(13) . ?
N14 C10 1.179(15) . ?
N16 C13 1.334(14) . ?
N16 H16A 0.8641 . ?
N16 H16B 0.8644 . ?
N13 C8 1.312(13) . ?
N13 H13A 0.8602 . ?
N13 H13B 0.8602 . ?
C1 C6 1.368(16) . ?
C1 C2 1.397(17) . ?
C2 C3 1.42(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.30(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.36(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C19 C18 1.354(17) . ?
C19 C20 1.436(16) . ?
C19 H19 0.9300 . ?
C20 C15 1.360(15) . ?
C20 H20 0.9300 . ?
C15 C16 1.401(16) . ?
C15 C11 1.572(16) . ?
C16 C17 1.367(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.334(17) . ?
C17 H17 0.9300 . ?
C10 C9 1.386(16) . ?
C14 C12 1.416(15) . ?
C11 C12 1.448(15) . ?
C11 C9 1.509(14) . ?
C11 H11 0.9800 . ?
C8 N12 1.367(13) . ?
C8 C9 1.375(16) . ?
C13 N12 1.390(13) . ?
C13 C12 1.429(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C7 N12 117.4(9) . . ?
C1 C7 H7A 108.0 . . ?
N12 C7 H7A 108.0 . . ?
C1 C7 H7B 108.0 . . ?
N12 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
C13 N16 H16A 108.9 . . ?
C13 N16 H16B 109.4 . . ?
H16A N16 H16B 108.8 . . ?
C8 N13 H13A 109.0 . . ?
C8 N13 H13B 109.6 . . ?
H13A N13 H13B 109.5 . . ?
C6 C1 C2 119.1(12) . . ?
C6 C1 C7 118.5(11) . . ?
C2 C1 C7 122.4(12) . . ?
C1 C2 C3 117.3(14) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 124.8(16) . . ?
C4 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
C3 C4 C5 117.4(15) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 122.3(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 119.1(13) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C18 C19 C20 119.0(11) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 119.1(11) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C15 C16 118.5(11) . . ?
C20 C15 C11 121.2(10) . . ?
C16 C15 C11 120.3(10) . . ?
C17 C16 C15 121.8(12) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C16 119.1(12) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 122.5(11) . . ?
C17 C18 Cl1 119.9(9) . . ?
C19 C18 Cl1 117.4(10) . . ?
N14 C10 C9 178.6(14) . . ?
N15 C14 C12 177.4(12) . . ?
C12 C11 C9 109.3(9) . . ?
C12 C11 C15 112.9(9) . . ?
C9 C11 C15 112.6(8) . . ?
C12 C11 H11 107.2 . . ?
C9 C11 H11 107.2 . . ?
C15 C11 H11 107.2 . . ?
N13 C8 N12 117.6(11) . . ?
N13 C8 C9 124.0(11) . . ?
N12 C8 C9 118.4(9) . . ?
N16 C13 N12 119.4(10) . . ?
N16 C13 C12 122.9(10) . . ?
N12 C13 C12 117.6(10) . . ?
C14 C12 C13 119.4(10) . . ?
C14 C12 C11 121.5(10) . . ?
C13 C12 C11 119.1(9) . . ?
C8 C9 C10 118.6(10) . . ?
C8 C9 C11 120.0(9) . . ?
C10 C9 C11 121.2(10) . . ?
C8 N12 C13 121.9(9) . . ?
C8 N12 C7 120.2(9) . . ?
C13 N12 C7 117.6(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
N12 C7 C1 C6 173.7(11) . . . . ?
N12 C7 C1 C2 -8.6(17) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
C7 C1 C2 C3 -177.0(13) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 C6 1(3) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
C7 C1 C6 C5 178.3(12) . . . . ?
C4 C5 C6 C1 -2(2) . . . . ?
C18 C19 C20 C15 -1.4(19) . . . . ?
C19 C20 C15 C16 0.0(18) . . . . ?
C19 C20 C15 C11 -179.1(10) . . . . ?
C20 C15 C16 C17 0(2) . . . . ?
C11 C15 C16 C17 179.2(12) . . . . ?
C15 C16 C17 C18 1(2) . . . . ?
C16 C17 C18 C19 -3(2) . . . . ?
C16 C17 C18 Cl1 -178.5(11) . . . . ?
C20 C19 C18 C17 3(2) . . . . ?
C20 C19 C18 Cl1 178.7(10) . . . . ?
C20 C15 C11 C12 -14.8(15) . . . . ?
C16 C15 C11 C12 166.2(11) . . . . ?
C20 C15 C11 C9 109.6(12) . . . . ?
C16 C15 C11 C9 -69.5(13) . . . . ?
N15 C14 C12 C13 -170(28) . . . . ?
N15 C14 C12 C11 9(29) . . . . ?
N16 C13 C12 C14 9.8(17) . . . . ?
N12 C13 C12 C14 -167.5(9) . . . . ?
N16 C13 C12 C11 -169.4(10) . . . . ?
N12 C13 C12 C11 13.4(15) . . . . ?
C9 C11 C12 C14 143.7(10) . . . . ?
C15 C11 C12 C14 -90.1(12) . . . . ?
C9 C11 C12 C13 -37.2(13) . . . . ?
C15 C11 C12 C13 89.0(12) . . . . ?
N13 C8 C9 C10 -5.4(16) . . . . ?
N12 C8 C9 C10 174.8(10) . . . . ?
N13 C8 C9 C11 168.9(10) . . . . ?
N12 C8 C9 C11 -10.9(14) . . . . ?
N14 C10 C9 C8 142(57) . . . . ?
N14 C10 C9 C11 -32(58) . . . . ?
C12 C11 C9 C8 36.7(13) . . . . ?
C15 C11 C9 C8 -89.6(12) . . . . ?
C12 C11 C9 C10 -149.2(10) . . . . ?
C15 C11 C9 C10 84.5(12) . . . . ?
N13 C8 N12 C13 162.7(10) . . . . ?
C9 C8 N12 C13 -17.5(14) . . . . ?
N13 C8 N12 C7 -24.2(14) . . . . ?
C9 C8 N12 C7 155.6(9) . . . . ?
N16 C13 N12 C8 -160.8(10) . . . . ?
C12 C13 N12 C8 16.6(14) . . . . ?
N16 C13 N12 C7 26.0(14) . . . . ?
C12 C13 N12 C7 -156.7(9) . . . . ?
C1 C7 N12 C8 98.0(12) . . . . ?
C1 C7 N12 C13 -88.6(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.138
_database_code_depnum_ccdc_archive 'CCDC 913525'
