# 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_complex1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(Cl)'
_chemical_formula_sum            'C14 H20 Cl2 N4'
_chemical_formula_weight         315.24

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

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

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

_cell_length_a                   5.1940(3)
_cell_length_b                   4.9806(4)
_cell_length_c                   30.954(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.717(6)
_cell_angle_gamma                90.00
_cell_volume                     800.40(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    675
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      26.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2325
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1551
_reflns_number_gt                1255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group.
;

_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)+(0.0263P)²+0.9571P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     97
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_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 -0.02281(14) 0.86135(18) 0.43916(3) 0.0391(3) Uani 1 1 d . . .
N1 N 0.2853(7) 0.6885(9) 0.27969(10) 0.0624(11) Uani 1 1 d . . .
N2 N 0.4768(5) 0.5244(5) 0.43919(8) 0.0273(6) Uani 1 1 d D . .
H2N1 H 0.340(3) 0.623(5) 0.4381(10) 0.041 Uiso 1 1 d D . .
H2N2 H 0.607(3) 0.629(5) 0.4360(10) 0.041 Uiso 1 1 d D . .
C1 C 0.4843(8) 0.7718(9) 0.30361(12) 0.0576(11) Uani 1 1 d . . .
H1A H 0.5840 0.9104 0.2929 0.069 Uiso 1 1 calc R . .
C2 C 0.5537(7) 0.6667(8) 0.34340(11) 0.0427(9) Uani 1 1 d . . .
H2A H 0.6961 0.7335 0.3588 0.051 Uiso 1 1 calc R . .
C3 C 0.4086(6) 0.4599(7) 0.36017(10) 0.0334(8) Uani 1 1 d . . .
C4 C 0.2004(7) 0.3726(9) 0.33558(12) 0.0503(10) Uani 1 1 d . . .
H4A H 0.0958 0.2359 0.3456 0.060 Uiso 1 1 calc R . .
C5 C 0.1478(8) 0.4898(11) 0.29580(13) 0.0646(13) Uani 1 1 d . . .
H5A H 0.0080 0.4257 0.2794 0.077 Uiso 1 1 calc R . .
C6 C 0.4769(6) 0.3263(7) 0.40263(10) 0.0351(8) Uani 1 1 d . . .
H6A H 0.3536 0.1849 0.4080 0.042 Uiso 1 1 calc R . .
H6B H 0.6461 0.2450 0.4011 0.042 Uiso 1 1 calc R . .
C7 C 0.4981(6) 0.3952(6) 0.48253(9) 0.0285(7) Uani 1 1 d . . .
H7A H 0.6548 0.2895 0.4847 0.034 Uiso 1 1 calc R . .
H7B H 0.3532 0.2754 0.4862 0.034 Uiso 1 1 calc R . .

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 0.0233(4) 0.0406(5) 0.0534(5) 0.0025(4) -0.0002(3) 0.0020(4)
N1 0.073(2) 0.079(3) 0.0340(17) -0.0022(19) -0.0101(16) 0.021(2)
N2 0.0224(12) 0.0310(14) 0.0284(13) 0.0052(12) 0.0013(10) 0.0035(12)
C1 0.069(3) 0.065(3) 0.039(2) 0.010(2) 0.0049(18) 0.007(2)
C2 0.0453(19) 0.048(2) 0.0344(18) 0.0047(18) -0.0029(14) -0.0022(19)
C3 0.0348(17) 0.0356(18) 0.0298(16) -0.0047(15) -0.0001(13) 0.0119(16)
C4 0.0400(19) 0.065(3) 0.045(2) -0.012(2) -0.0034(15) -0.003(2)
C5 0.053(2) 0.090(4) 0.049(2) -0.020(3) -0.0187(19) 0.013(3)
C6 0.0404(18) 0.0275(18) 0.0371(18) -0.0004(15) -0.0017(14) 0.0037(16)
C7 0.0310(15) 0.0234(16) 0.0309(15) 0.0064(14) 0.0000(12) 0.0038(14)

_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 C1 1.320(5) . ?
N1 C5 1.327(6) . ?
N2 C7 1.489(4) . ?
N2 C6 1.501(4) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.376(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.386(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 C6 1.506(4) . ?
C4 C5 1.383(6) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.503(6) 3_666 ?
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
C1 N1 C5 116.4(4) . . ?
C7 N2 C6 113.2(2) . . ?
C7 N2 H2N1 109(2) . . ?
C6 N2 H2N1 111(2) . . ?
C7 N2 H2N2 109(2) . . ?
C6 N2 H2N2 107(2) . . ?
H2N1 N2 H2N2 107.6(16) . . ?
N1 C1 C2 124.2(4) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C6 120.3(3) . . ?
C2 C3 C6 122.6(3) . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
N2 C6 C3 111.2(3) . . ?
N2 C6 H6A 109.4 . . ?
C3 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C3 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C7 110.3(3) . 3_666 ?
N2 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 3_666 . ?
N2 C7 H7B 109.6 . . ?
C7 C7 H7B 109.6 3_666 . ?
H7A C7 H7B 108.1 . . ?

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
C5 N1 C1 C2 -0.3(6) . . . . ?
N1 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C2 C3 C6 177.6(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C6 C3 C4 C5 -177.1(3) . . . . ?
C1 N1 C5 C4 0.9(6) . . . . ?
C3 C4 C5 N1 -1.2(6) . . . . ?
C7 N2 C6 C3 170.0(2) . . . . ?
C4 C3 C6 N2 -121.8(3) . . . . ?
C2 C3 C6 N2 60.4(4) . . . . ?
C6 N2 C7 C7 178.9(3) . . . 3_666 ?

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
N2 H2N1 Cl1 0.86(3) 2.230(10) 3.090(3) 176(3) .
N2 H2N2 Cl1 0.86(3) 2.243(11) 3.094(3) 169(3) 1_655

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 996128'
#######################################################################
#
#                 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_complex2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(Cl)'
_chemical_formula_sum            'C14 H20 Cl2 N4'
_chemical_formula_weight         315.24

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

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

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

_cell_length_a                   5.2548(4)
_cell_length_b                   4.8972(4)
_cell_length_c                   31.167(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.400(7)
_cell_angle_gamma                90.00
_cell_volume                     801.33(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9205
_exptl_absorpt_correction_T_max  0.9460
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2152
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         27.54
_reflns_number_total             1855
_reflns_number_gt                1172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group.
;

_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)+(0.0009P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.071(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1855
_refine_ls_number_parameters     98
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.02594(16) 0.86709(17) 0.56065(3) 0.0404(3) Uani 1 1 d . . .
N1 N 0.8939(10) 0.5229(12) 0.69901(14) 0.108(2) Uani 1 1 d . . .
N2 N 0.5271(5) 0.5330(5) 0.56000(9) 0.0275(6) Uani 1 1 d D . .
H2N1 H 0.670(3) 0.617(5) 0.5617(10) 0.041 Uiso 1 1 d D . .
H2N2 H 0.408(4) 0.650(5) 0.5630(10) 0.041 Uiso 1 1 d D . .
C1 C 0.8190(9) 0.4057(12) 0.66182(14) 0.0741(14) Uani 1 1 d . . .
H1A H 0.9204 0.2688 0.6509 0.089 Uiso 1 1 calc R . .
C2 C 0.5956(8) 0.4785(8) 0.63852(12) 0.0475(10) Uani 1 1 d . . .
C3 C 0.4503(9) 0.6830(8) 0.65595(11) 0.0594(12) Uani 1 1 d . . .
H3A H 0.3007 0.7418 0.6418 0.071 Uiso 1 1 calc R . .
C4 C 0.5313(13) 0.7989(10) 0.69478(15) 0.091(2) Uani 1 1 d . . .
H4A H 0.4372 0.9396 0.7064 0.109 Uiso 1 1 calc R . .
C5 C 0.7369(13) 0.7134(16) 0.71513(16) 0.105(3) Uani 1 1 d . . .
H5A H 0.7784 0.7864 0.7421 0.126 Uiso 1 1 calc R . .
C6 C 0.5264(6) 0.3383(6) 0.59721(10) 0.0364(8) Uani 1 1 d . . .
H6A H 0.3585 0.2578 0.5989 0.044 Uiso 1 1 calc R . .
H6B H 0.6469 0.1923 0.5926 0.044 Uiso 1 1 calc R . .
C7 C 0.5027(6) 0.3970(6) 0.51775(9) 0.0302(7) Uani 1 1 d . . .
H7A H 0.3474 0.2899 0.5160 0.036 Uiso 1 1 calc R . .
H7B H 0.6453 0.2739 0.5145 0.036 Uiso 1 1 calc R . .

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 0.0233(4) 0.0402(5) 0.0575(6) -0.0029(4) -0.0016(3) -0.0060(5)
N1 0.081(4) 0.189(6) 0.052(3) 0.031(3) -0.035(2) -0.051(4)
N2 0.0189(12) 0.0308(12) 0.0326(14) -0.0032(12) -0.0024(11) -0.0075(12)
C1 0.051(3) 0.109(4) 0.060(3) 0.016(3) -0.012(2) 0.003(3)
C2 0.050(2) 0.053(2) 0.039(2) 0.0150(17) -0.0005(17) -0.020(2)
C3 0.088(4) 0.054(2) 0.035(2) -0.0050(18) -0.001(2) -0.008(2)
C4 0.145(6) 0.086(4) 0.044(3) -0.026(3) 0.020(3) -0.028(4)
C5 0.115(6) 0.159(6) 0.039(3) 0.005(3) -0.015(3) -0.080(5)
C6 0.0290(18) 0.0352(18) 0.0443(19) 0.0040(15) -0.0059(14) -0.0074(16)
C7 0.0312(17) 0.0256(14) 0.0332(16) -0.0031(14) -0.0048(13) -0.0051(15)

_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 C1 1.338(6) . ?
N1 C5 1.356(8) . ?
N2 C7 1.476(4) . ?
N2 C6 1.501(4) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.400(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.385(5) . ?
C2 C6 1.490(5) . ?
C3 C4 1.387(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.299(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.496(6) 3_666 ?
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
C1 N1 C5 117.0(5) . . ?
C7 N2 C6 113.6(2) . . ?
C7 N2 H2N1 108(2) . . ?
C6 N2 H2N1 107(2) . . ?
C7 N2 H2N2 111(2) . . ?
C6 N2 H2N2 108(2) . . ?
H2N1 N2 H2N2 108.3(15) . . ?
N1 C1 C2 123.4(5) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C3 C2 C1 116.4(4) . . ?
C3 C2 C6 123.6(4) . . ?
C1 C2 C6 120.0(4) . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 120.8(6) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 N1 123.2(5) . . ?
C4 C5 H5A 118.4 . . ?
N1 C5 H5A 118.4 . . ?
C2 C6 N2 111.5(2) . . ?
C2 C6 H6A 109.3 . . ?
N2 C6 H6A 109.3 . . ?
C2 C6 H6B 109.3 . . ?
N2 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C7 110.7(3) . 3_666 ?
N2 C7 H7A 109.5 . . ?
C7 C7 H7A 109.5 3_666 . ?
N2 C7 H7B 109.5 . . ?
C7 C7 H7B 109.5 3_666 . ?
H7A C7 H7B 108.1 . . ?

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
C5 N1 C1 C2 2.8(8) . . . . ?
N1 C1 C2 C3 0.0(7) . . . . ?
N1 C1 C2 C6 179.7(4) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C6 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C3 C4 C5 N1 4.7(9) . . . . ?
C1 N1 C5 C4 -5.2(9) . . . . ?
C3 C2 C6 N2 64.0(4) . . . . ?
C1 C2 C6 N2 -115.8(4) . . . . ?
C7 N2 C6 C2 170.2(3) . . . . ?
C6 N2 C7 C7 178.4(3) . . . 3_666 ?

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
N2 H2N1 Cl1 0.86(3) 2.237(11) 3.089(3) 174(3) .
N2 H2N2 Cl1 0.86(3) 2.268(12) 3.101(3) 163(3) 1_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 996129'
#######################################################################
#
#                 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_complex3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(N O3), (H2 O)'
_chemical_formula_sum            'C14 H22 N6 O7'
_chemical_formula_weight         386.36

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'

_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                   5.6626(5)
_cell_length_b                   5.7272(4)
_cell_length_c                   14.4655(13)
_cell_angle_alpha                80.726(7)
_cell_angle_beta                 84.609(7)
_cell_angle_gamma                89.403(7)
_cell_volume                     460.94(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    980
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      26.31

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             202
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3252
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1866
_reflns_number_gt                1427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group.
 For the H₂M1²⁺ cation in this salt, SADI, EADP and ISOR were used to 
 refine the disorder.
;

_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)+(0.0718P)²+0.2337P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     133
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.3523(3) 0.5084(3) 0.39006(13) 0.0552(5) Uani 1 1 d . . .
O2 O 0.0668(3) 0.3007(3) 0.36023(15) 0.0646(6) Uani 1 1 d . . .
O3 O 0.0124(4) 0.6679(4) 0.37511(18) 0.0846(7) Uani 1 1 d . . .
O1W O 0.0954(11) 0.6180(11) -0.0824(4) 0.1159(19) Uani 0.50 1 d P . .
N2 N 0.4667(3) 0.9907(3) 0.37316(11) 0.0319(4) Uani 1 1 d D A .
H2N1 H 0.421(3) 0.8465(17) 0.3803(17) 0.048 Uiso 1 1 d D . .
H2N2 H 0.346(3) 1.083(3) 0.3701(17) 0.048 Uiso 1 1 d D . .
N3 N 0.1409(3) 0.4945(3) 0.37496(13) 0.0431(5) Uani 1 1 d . . .
C1 C 0.4844(13) 0.9793(14) 0.2044(6) 0.0423(11) Uani 0.50 1 d PGDU A 1
C2 C 0.5562(10) 0.7758(12) 0.1688(5) 0.0564(14) Uani 0.50 1 d PGU A 1
H2 H 0.6847 0.6899 0.1915 0.068 Uiso 0.50 1 calc PR A 1
C3 C 0.4360(9) 0.7009(8) 0.0993(4) 0.0709(16) Uani 0.50 1 d PGU A 1
H3 H 0.4841 0.5647 0.0755 0.085 Uiso 0.50 1 calc PR A 1
N1 N 0.2440(8) 0.8294(8) 0.0654(3) 0.0729(13) Uani 0.50 1 d PGU A 1
C4 C 0.1722(9) 1.0329(8) 0.1010(4) 0.0688(15) Uani 0.50 1 d PGU A 1
H4 H 0.0437 1.1189 0.0783 0.083 Uiso 0.50 1 calc PR A 1
C5 C 0.2924(13) 1.1078(11) 0.1705(5) 0.0554(13) Uani 0.50 1 d PGU A 1
H5 H 0.2444 1.2440 0.1942 0.067 Uiso 0.50 1 calc PR A 1
C1' C 0.5289(13) 0.9397(14) 0.2052(6) 0.0423(11) Uani 0.50 1 d PGD A 2
C2' C 0.6460(10) 0.7494(13) 0.1732(5) 0.0564(14) Uani 0.50 1 d PG A 2
H2' H 0.7852 0.6930 0.1979 0.068 Uiso 0.50 1 calc PR A 2
C3' C 0.5550(8) 0.6435(9) 0.1040(4) 0.0709(16) Uani 0.50 1 d PG A 2
H3' H 0.6333 0.5162 0.0826 0.085 Uiso 0.50 1 calc PR A 2
N1' N 0.3469(8) 0.7278(8) 0.0670(3) 0.0729(13) Uani 0.50 1 d PG A 2
C4' C 0.2298(8) 0.9181(9) 0.0991(4) 0.0688(15) Uani 0.50 1 d PG A 2
H4' H 0.0906 0.9745 0.0743 0.083 Uiso 0.50 1 calc PR A 2
C5' C 0.3208(12) 1.0240(11) 0.1682(5) 0.0554(13) Uani 0.50 1 d PG A 2
H5' H 0.2425 1.1513 0.1896 0.067 Uiso 0.50 1 calc PR A 2
C6 C 0.6188(4) 1.0496(4) 0.28269(14) 0.0413(5) Uani 1 1 d D . .
H6A H 0.7673 0.9640 0.2863 0.050 Uiso 0.50 1 calc PR A 1
H6B H 0.6540 1.2177 0.2698 0.050 Uiso 0.50 1 calc PR A 1
H6C H 0.7783 0.9937 0.2923 0.050 Uiso 0.50 1 d PR A 2
H6D H 0.6262 1.2201 0.2643 0.050 Uiso 0.50 1 d PR A 2
C7 C 0.5886(3) 1.0223(4) 0.45687(13) 0.0320(4) Uani 1 1 d . . .
H7A H 0.653(4) 1.176(4) 0.4466(15) 0.038 Uiso 1 1 d . . .
H7B H 0.723(4) 0.910(4) 0.4600(15) 0.038 Uiso 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
O1 0.0465(10) 0.0349(8) 0.0874(13) -0.0103(8) -0.0223(8) -0.0026(6)
O2 0.0488(10) 0.0512(10) 0.1001(15) -0.0260(10) -0.0137(9) -0.0119(8)
O3 0.0645(13) 0.0590(12) 0.131(2) -0.0192(12) -0.0107(12) 0.0281(10)
O1W 0.122(4) 0.124(4) 0.117(4) -0.050(4) -0.043(4) 0.001(3)
N2 0.0366(9) 0.0290(8) 0.0326(9) -0.0095(7) -0.0071(7) -0.0028(6)
N3 0.0424(10) 0.0354(9) 0.0520(11) -0.0089(8) -0.0047(8) 0.0028(7)
C1 0.049(3) 0.048(2) 0.0298(11) -0.0075(14) -0.0004(15) -0.0104(18)
C2 0.065(4) 0.059(2) 0.0477(16) -0.0179(15) -0.005(3) -0.005(3)
C3 0.086(5) 0.072(3) 0.061(2) -0.029(2) -0.007(3) -0.005(3)
N1 0.084(4) 0.086(3) 0.0538(18) -0.025(2) -0.013(2) -0.005(2)
C4 0.073(3) 0.087(5) 0.0522(19) -0.019(3) -0.018(2) -0.004(3)
C5 0.058(2) 0.071(4) 0.0414(14) -0.016(2) -0.0124(14) -0.005(3)
C1' 0.049(3) 0.048(2) 0.0298(11) -0.0075(14) -0.0004(15) -0.0104(18)
C2' 0.065(4) 0.059(2) 0.0477(16) -0.0179(15) -0.005(3) -0.005(3)
C3' 0.086(5) 0.072(3) 0.061(2) -0.029(2) -0.007(3) -0.005(3)
N1' 0.084(4) 0.086(3) 0.0538(18) -0.025(2) -0.013(2) -0.005(2)
C4' 0.073(3) 0.087(5) 0.0522(19) -0.019(3) -0.018(2) -0.004(3)
C5' 0.058(2) 0.071(4) 0.0414(14) -0.016(2) -0.0124(14) -0.005(3)
C6 0.0448(12) 0.0473(12) 0.0328(11) -0.0092(9) -0.0026(9) -0.0086(9)
C7 0.0317(10) 0.0341(10) 0.0327(10) -0.0097(8) -0.0088(8) -0.0003(8)

_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
O1 N3 1.243(2) . ?
O2 N3 1.248(2) . ?
O3 N3 1.225(2) . ?
N2 C7 1.485(2) . ?
N2 C6 1.490(3) . ?
N2 H2N1 0.86(2) . ?
N2 H2N2 0.86(2) . ?
C1 C2 1.3900 . ?
C1 C5 1.3900 . ?
C1 C6 1.529(4) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 N1 1.3900 . ?
C3 H3 0.9300 . ?
N1 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C1' C2' 1.3900 . ?
C1' C5' 1.3900 . ?
C1' C6 1.501(4) . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9300 . ?
C3' N1' 1.3900 . ?
C3' H3' 0.9300 . ?
N1' C4' 1.3900 . ?
C4' C5' 1.3900 . ?
C4' H4' 0.9300 . ?
C5' H5' 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9701 . ?
C7 C7 1.515(4) 2_676 ?
C7 H7A 0.94(2) . ?
C7 H7B 0.99(2) . ?

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
C7 N2 C6 113.56(15) . . ?
C7 N2 H2N1 107.9(16) . . ?
C6 N2 H2N1 109.5(16) . . ?
C7 N2 H2N2 108.6(16) . . ?
C6 N2 H2N2 107.5(16) . . ?
H2N1 N2 H2N2 109.7(14) . . ?
O3 N3 O1 119.94(19) . . ?
O3 N3 O2 122.2(2) . . ?
O1 N3 O2 117.91(17) . . ?
C2 C1 C5 120.0 . . ?
C2 C1 C6 117.7(4) . . ?
C5 C1 C6 122.2(4) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C3 C2 120.0 . . ?
N1 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 N1 C4 120.0 . . ?
C5 C4 N1 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C4 H4 120.0 . . ?
C4 C5 C1 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C5 H5 120.0 . . ?
C2' C1' C5' 120.0 . . ?
C2' C1' C6 120.7(4) . . ?
C5' C1' C6 119.2(4) . . ?
C1' C2' C3' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C2' C3' N1' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
N1' C3' H3' 120.0 . . ?
C3' N1' C4' 120.0 . . ?
C5' C4' N1' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
N1' C4' H4' 120.0 . . ?
C4' C5' C1' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C1' C5' H5' 120.0 . . ?
N2 C6 C1' 112.4(4) . . ?
N2 C6 C1 108.2(4) . . ?
N2 C6 H6A 110.1 . . ?
C1' C6 H6A 97.5 . . ?
C1 C6 H6A 110.1 . . ?
N2 C6 H6B 110.1 . . ?
C1' C6 H6B 117.5 . . ?
C1 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C6 H6C 108.7 . . ?
C1' C6 H6C 109.1 . . ?
C1 C6 H6C 121.5 . . ?
H6B C6 H6C 97.8 . . ?
N2 C6 H6D 109.2 . . ?
C1' C6 H6D 109.5 . . ?
C1 C6 H6D 100.8 . . ?
H6A C6 H6D 117.9 . . ?
H6C C6 H6D 107.9 . . ?
N2 C7 C7 108.71(19) . 2_676 ?
N2 C7 H7A 108.3(13) . . ?
C7 C7 H7A 112.5(13) 2_676 . ?
N2 C7 H7B 106.8(12) . . ?
C7 C7 H7B 112.8(13) 2_676 . ?
H7A C7 H7B 107.4(18) . . ?

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
C5 C1 C2 C3 0.0 . . . . ?
C6 C1 C2 C3 178.3(8) . . . . ?
C1 C2 C3 N1 0.0 . . . . ?
C2 C3 N1 C4 0.0 . . . . ?
C3 N1 C4 C5 0.0 . . . . ?
N1 C4 C5 C1 0.0 . . . . ?
C2 C1 C5 C4 0.0 . . . . ?
C6 C1 C5 C4 -178.2(8) . . . . ?
C5' C1' C2' C3' 0.0 . . . . ?
C6 C1' C2' C3' 177.4(8) . . . . ?
C1' C2' C3' N1' 0.0 . . . . ?
C2' C3' N1' C4' 0.0 . . . . ?
C3' N1' C4' C5' 0.0 . . . . ?
N1' C4' C5' C1' 0.0 . . . . ?
C2' C1' C5' C4' 0.0 . . . . ?
C6 C1' C5' C4' -177.4(8) . . . . ?
C7 N2 C6 C1' 159.9(3) . . . . ?
C7 N2 C6 C1 172.7(3) . . . . ?
C2' C1' C6 N2 -107.2(5) . . . . ?
C5' C1' C6 N2 70.2(5) . . . . ?
C2' C1' C6 C1 180(4) . . . . ?
C5' C1' C6 C1 -3(3) . . . . ?
C2 C1 C6 N2 -104.9(4) . . . . ?
C5 C1 C6 N2 73.4(5) . . . . ?
C2 C1 C6 C1' 7(3) . . . . ?
C5 C1 C6 C1' -175(4) . . . . ?
C6 N2 C7 C7 175.27(19) . . . 2_676 ?

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
N2 H2N1 O1 0.86(2) 1.959(9) 2.811(2) 173(2) .
N2 H2N1 O3 0.86(2) 2.550(17) 3.179(3) 131.1(16) .
N2 H2N2 O2 0.86(2) 2.006(10) 2.864(2) 179(2) 1_565
N2 H2N2 O1 0.86(2) 2.502(16) 3.071(2) 124.6(17) 1_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 996130'
#######################################################################
#
#                 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_complex4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(N O3)'
_chemical_formula_sum            'C14 H20 N6 O6'
_chemical_formula_weight         368.36

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'

_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                   5.7604(12)
_cell_length_b                   5.6367(11)
_cell_length_c                   27.451(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                90.00
_cell_volume                     889.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3579
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      27.38

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8231
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2025
_reflns_number_gt                1054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group.
;

_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)+(0.0816P)²+0.2902P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2025
_refine_ls_number_parameters     124
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
O1 O 0.4151(4) -0.0267(4) 0.06656(10) 0.0866(8) Uani 1 1 d . . .
O2 O 0.7864(3) 0.0309(4) 0.07555(9) 0.0736(7) Uani 1 1 d . . .
O3 O 0.5584(3) 0.3164(4) 0.05345(8) 0.0652(6) Uani 1 1 d . . .
N1 N 0.6034(5) 0.4110(7) 0.19574(12) 0.0848(9) Uani 1 1 d . . .
N2 N 0.0881(3) 0.4296(4) 0.06499(8) 0.0437(5) Uani 1 1 d D . .
H2N1 H 0.229(2) 0.381(4) 0.0610(11) 0.066 Uiso 1 1 d D . .
H2N2 H 0.002(3) 0.304(3) 0.0667(11) 0.066 Uiso 1 1 d D . .
N3 N 0.5852(3) 0.1039(4) 0.06533(8) 0.0522(6) Uani 1 1 d . . .
C1 C 0.4539(5) 0.5140(6) 0.16382(11) 0.0633(8) Uani 1 1 d . . .
H1 H 0.5005 0.6533 0.1491 0.076 Uiso 1 1 calc R . .
C2 C 0.2341(4) 0.4291(5) 0.15094(9) 0.0470(6) Uani 1 1 d . . .
C3 C 0.1656(5) 0.2225(5) 0.17300(11) 0.0611(8) Uani 1 1 d . . .
H3 H 0.0185 0.1593 0.1656 0.073 Uiso 1 1 calc R . .
C4 C 0.3189(7) 0.1113(6) 0.20612(12) 0.0752(10) Uani 1 1 d . . .
H4 H 0.2775 -0.0284 0.2214 0.090 Uiso 1 1 calc R . .
C5 C 0.5334(7) 0.2111(8) 0.21603(13) 0.0859(12) Uani 1 1 d . . .
H5 H 0.6360 0.1346 0.2382 0.103 Uiso 1 1 calc R . .
C6 C 0.0847(4) 0.5566(5) 0.11292(10) 0.0506(7) Uani 1 1 d . . .
H6A H 0.1414 0.7174 0.1094 0.061 Uiso 1 1 calc R . .
H6B H -0.0737 0.5650 0.1230 0.061 Uiso 1 1 calc R . .
C7 C 0.0031(4) 0.5767(4) 0.02264(9) 0.0444(6) Uani 1 1 d . . .
H7A H 0.1062 0.7107 0.0189 0.053 Uiso 1 1 calc R . .
H7B H -0.1512 0.6369 0.0278 0.053 Uiso 1 1 calc R . .

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
O1 0.0614(13) 0.0717(15) 0.127(2) 0.0049(14) 0.0097(13) -0.0234(11)
O2 0.0494(11) 0.0591(13) 0.1103(19) -0.0008(12) -0.0102(11) 0.0130(9)
O3 0.0459(10) 0.0567(12) 0.0938(16) 0.0166(11) 0.0101(10) 0.0076(9)
N1 0.0626(16) 0.108(2) 0.081(2) -0.0055(18) -0.0223(14) 0.0100(16)
N2 0.0367(10) 0.0470(12) 0.0468(12) 0.0009(9) -0.0026(9) 0.0049(8)
N3 0.0424(12) 0.0513(13) 0.0627(15) -0.0028(11) 0.0020(10) -0.0026(10)
C1 0.0496(15) 0.073(2) 0.0661(19) -0.0029(16) -0.0081(13) -0.0027(13)
C2 0.0445(13) 0.0543(15) 0.0417(14) -0.0030(11) -0.0002(10) 0.0066(11)
C3 0.0644(17) 0.0626(18) 0.0566(17) 0.0038(14) 0.0043(14) 0.0007(14)
C4 0.103(3) 0.071(2) 0.0527(18) 0.0134(15) 0.0070(18) 0.0216(19)
C5 0.086(3) 0.110(3) 0.058(2) 0.000(2) -0.0182(18) 0.039(2)
C6 0.0477(13) 0.0522(15) 0.0513(15) -0.0029(12) -0.0022(11) 0.0059(11)
C7 0.0410(12) 0.0418(13) 0.0499(14) 0.0029(10) -0.0031(10) 0.0029(10)

_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
O1 N3 1.228(3) . ?
O2 N3 1.246(3) . ?
O3 N3 1.249(3) . ?
N1 C1 1.326(4) . ?
N1 C5 1.330(5) . ?
N2 C7 1.487(3) . ?
N2 C6 1.499(3) . ?
N2 H2N1 0.87(3) . ?
N2 H2N2 0.87(3) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(4) . ?
C2 C6 1.497(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.513(5) 3_565 ?
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
C1 N1 C5 116.5(3) . . ?
C7 N2 C6 113.5(2) . . ?
C7 N2 H2N1 110(2) . . ?
C6 N2 H2N1 109(2) . . ?
C7 N2 H2N2 110(2) . . ?
C6 N2 H2N2 108(2) . . ?
H2N1 N2 H2N2 107.1(15) . . ?
O1 N3 O2 121.9(2) . . ?
O1 N3 O3 119.7(2) . . ?
O2 N3 O3 118.4(2) . . ?
N1 C1 C2 124.6(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 117.5(3) . . ?
C1 C2 C6 119.5(3) . . ?
C3 C2 C6 122.9(2) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.8(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C2 C6 N2 110.2(2) . . ?
C2 C6 H6A 109.6 . . ?
N2 C6 H6A 109.6 . . ?
C2 C6 H6B 109.6 . . ?
N2 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 108.3(2) . 3_565 ?
N2 C7 H7A 110.0 . . ?
C7 C7 H7A 110.0 3_565 . ?
N2 C7 H7B 110.0 . . ?
C7 C7 H7B 110.0 3_565 . ?
H7A C7 H7B 108.4 . . ?

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
C5 N1 C1 C2 0.5(5) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
N1 C1 C2 C6 -177.6(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C6 C2 C3 C4 177.2(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C1 N1 C5 C4 -0.7(5) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C1 C2 C6 N2 101.4(3) . . . . ?
C3 C2 C6 N2 -76.3(3) . . . . ?
C7 N2 C6 C2 -163.3(2) . . . . ?
C6 N2 C7 C7 -175.5(2) . . . 3_565 ?

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
N2 H2N1 O3 0.87(3) 1.957(10) 2.819(3) 172(2) .
N2 H2N1 O1 0.87(3) 2.54(2) 3.187(3) 132(2) .
N2 H2N2 O2 0.87(3) 2.004(10) 2.866(3) 175(3) 1_455
N2 H2N2 O3 0.87(3) 2.56(2) 3.115(3) 123(2) 1_455

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 996131'
#######################################################################
#
#                 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_complex5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(N O3), 2(H2 O)'
_chemical_formula_sum            'C14 H24 N6 O8'
_chemical_formula_weight         404.39

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   12.3246(6)
_cell_length_b                   11.0455(5)
_cell_length_c                   15.1138(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.214(4)
_cell_angle_gamma                90.00
_cell_volume                     1975.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1855
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      25.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8215
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3878
_reflns_number_gt                2738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and O atoms, N and H atoms, as well as O and H atoms. 
 Such restraint was mainly employed to define an appropriate geometry for 
 the -NH₂ groups and water molecules.
;

_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)+(0.0661P)²+0.3053P] 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       0.0060(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3878
_refine_ls_number_parameters     281
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.069
_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
O1W O 0.25804(13) 0.60726(15) 0.18208(10) 0.0500(4) Uani 1 1 d D . .
H1W1 H 0.259(2) 0.6485(19) 0.2309(11) 0.075 Uiso 1 1 d D . .
H1W2 H 0.3058(18) 0.5487(16) 0.1991(15) 0.075 Uiso 1 1 d D . .
O1 O 0.25957(16) 0.75880(16) -0.16218(11) 0.0639(5) Uani 1 1 d . . .
O2W O 0.56452(12) 0.93131(14) 0.26008(10) 0.0456(4) Uani 1 1 d GD . .
H2W1 H 0.5132(16) 0.9862(17) 0.2439(16) 0.068 Uiso 1 1 d D . .
H2W2 H 0.5463(19) 0.8874(18) 0.3013(14) 0.068 Uiso 1 1 d D . .
O2 O 0.28117(17) 0.58218(16) -0.10356(12) 0.0697(5) Uani 1 1 d . . .
O3 O 0.28111(17) 0.60696(19) -0.24528(12) 0.0795(6) Uani 1 1 d . . .
O4 O 0.54645(17) 0.91219(14) -0.06679(11) 0.0668(5) Uani 1 1 d . . .
O5 O 0.54967(15) 0.72268(15) -0.09766(10) 0.0584(5) Uani 1 1 d . . .
O6 O 0.55921(15) 0.85546(16) -0.19962(10) 0.0616(5) Uani 1 1 d . . .
N1 N -0.03969(18) 0.8631(2) -0.05207(16) 0.0735(7) Uani 1 1 d . . .
N2 N 0.25545(13) 0.75323(15) 0.03436(10) 0.0334(4) Uani 1 1 d D . .
H2N1 H 0.2511(18) 0.7101(16) -0.0145(9) 0.050 Uiso 1 1 d D . .
H2N2 H 0.2519(19) 0.7043(15) 0.0780(9) 0.050 Uiso 1 1 d D . .
N3 N 0.57161(13) 0.78695(15) 0.10530(11) 0.0350(4) Uani 1 1 d D . .
H3N1 H 0.5800(18) 0.8329(16) 0.1530(9) 0.053 Uiso 1 1 d D . .
H3N2 H 0.5731(19) 0.8326(16) 0.0591(9) 0.053 Uiso 1 1 d D . .
N4 N 0.77853(14) 0.88370(18) 0.15457(12) 0.0465(5) Uani 1 1 d . . .
N5 N 0.27472(15) 0.6485(2) -0.17134(12) 0.0495(5) Uani 1 1 d . . .
N6 N 0.55162(14) 0.83027(17) -0.12135(11) 0.0410(4) Uani 1 1 d . . .
C1 C -0.1450(2) 0.8159(3) -0.0919(2) 0.0728(8) Uani 1 1 d . . .
H1 H -0.2068 0.8677 -0.1093 0.087 Uiso 1 1 calc R . .
C2 C -0.1607(2) 0.6955(3) -0.10638(18) 0.0631(7) Uani 1 1 d . . .
H2 H -0.2324 0.6642 -0.1333 0.076 Uiso 1 1 calc R . .
C3 C -0.0690(2) 0.6213(3) -0.08051(18) 0.0647(7) Uani 1 1 d . . .
H3 H -0.0784 0.5384 -0.0903 0.078 Uiso 1 1 calc R . .
C4 C 0.03587(17) 0.6662(2) -0.04063(14) 0.0441(5) Uani 1 1 d . . .
H4 H 0.0981 0.6149 -0.0232 0.053 Uiso 1 1 calc R . .
C5 C 0.04746(16) 0.7844(2) -0.02719(13) 0.0379(5) Uani 1 1 d . . .
C6 C 0.16127(16) 0.84028(19) 0.01773(14) 0.0419(5) Uani 1 1 d . . .
H6A H 0.1748 0.9049 -0.0213 0.050 Uiso 1 1 calc R . .
H6B H 0.1598 0.8759 0.0760 0.050 Uiso 1 1 calc R . .
C7 C 0.36655(15) 0.81586(19) 0.06205(13) 0.0373(5) Uani 1 1 d . . .
H7A H 0.3715 0.8655 0.1160 0.045 Uiso 1 1 calc R . .
H7B H 0.3737 0.8684 0.0126 0.045 Uiso 1 1 calc R . .
C8 C 0.46054(16) 0.72458(19) 0.08333(13) 0.0370(5) Uani 1 1 d . . .
H8A H 0.4561 0.6753 0.1353 0.044 Uiso 1 1 calc R . .
H8B H 0.4528 0.6717 0.0307 0.044 Uiso 1 1 calc R . .
C9 C 0.66708(17) 0.7002(2) 0.12400(15) 0.0423(5) Uani 1 1 d . . .
H9A H 0.6598 0.6497 0.0702 0.051 Uiso 1 1 calc R . .
H9B H 0.6639 0.6481 0.1748 0.051 Uiso 1 1 calc R . .
C10 C 0.77934(16) 0.7638(2) 0.14738(13) 0.0397(5) Uani 1 1 d . . .
C11 C 0.87728(19) 0.6964(2) 0.16116(17) 0.0578(6) Uani 1 1 d . . .
H11 H 0.8743 0.6128 0.1539 0.069 Uiso 1 1 calc R . .
C12 C 0.9796(2) 0.7565(3) 0.18595(18) 0.0690(8) Uani 1 1 d . . .
H12 H 1.0470 0.7137 0.1960 0.083 Uiso 1 1 calc R . .
C13 C 0.9808(2) 0.8796(3) 0.19551(17) 0.0637(7) Uani 1 1 d . . .
H13 H 1.0487 0.9220 0.2129 0.076 Uiso 1 1 calc R . .
C14 C 0.87930(19) 0.9392(3) 0.17880(16) 0.0564(6) Uani 1 1 d . . .
H14 H 0.8805 1.0231 0.1846 0.068 Uiso 1 1 calc R . .

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
O1W 0.0549(10) 0.0461(10) 0.0481(8) 0.0065(7) 0.0131(7) 0.0034(8)
O1 0.0901(13) 0.0505(11) 0.0538(10) -0.0020(8) 0.0245(9) 0.0073(10)
O2W 0.0511(9) 0.0404(9) 0.0458(8) 0.0027(7) 0.0145(7) 0.0016(7)
O2 0.0984(14) 0.0506(11) 0.0603(10) -0.0005(9) 0.0226(10) -0.0005(10)
O3 0.0944(14) 0.0953(16) 0.0544(10) -0.0286(10) 0.0302(9) 0.0009(12)
O4 0.1185(15) 0.0404(10) 0.0487(9) -0.0098(8) 0.0353(10) -0.0143(10)
O5 0.0921(13) 0.0398(9) 0.0489(9) 0.0042(8) 0.0290(9) 0.0034(9)
O6 0.0874(12) 0.0668(12) 0.0373(8) 0.0135(8) 0.0283(8) 0.0135(10)
N1 0.0508(13) 0.0644(15) 0.0961(17) -0.0090(13) 0.0052(11) 0.0001(11)
N2 0.0316(9) 0.0347(10) 0.0323(8) -0.0026(7) 0.0060(7) -0.0042(7)
N3 0.0312(9) 0.0418(10) 0.0313(8) -0.0015(7) 0.0075(7) -0.0010(8)
N4 0.0368(10) 0.0525(12) 0.0505(10) -0.0023(9) 0.0126(8) -0.0009(9)
N5 0.0448(11) 0.0587(14) 0.0440(10) -0.0098(10) 0.0108(8) -0.0043(10)
N6 0.0439(10) 0.0445(11) 0.0353(9) 0.0000(9) 0.0122(7) -0.0009(8)
C1 0.0352(13) 0.070(2) 0.102(2) -0.0123(17) 0.0008(13) 0.0046(13)
C2 0.0347(12) 0.075(2) 0.0697(16) -0.0146(14) -0.0011(11) -0.0142(13)
C3 0.0594(16) 0.0506(15) 0.0760(16) -0.0102(13) 0.0059(13) -0.0062(13)
C4 0.0310(11) 0.0383(12) 0.0545(12) -0.0015(10) -0.0020(9) 0.0026(9)
C5 0.0312(10) 0.0435(13) 0.0359(10) -0.0015(9) 0.0044(8) -0.0006(9)
C6 0.0341(11) 0.0355(12) 0.0506(11) 0.0002(10) 0.0026(9) 0.0002(9)
C7 0.0311(10) 0.0379(12) 0.0407(10) -0.0026(9) 0.0062(8) -0.0062(9)
C8 0.0321(10) 0.0414(12) 0.0368(10) 0.0002(9) 0.0085(8) -0.0053(9)
C9 0.0373(11) 0.0445(13) 0.0450(11) 0.0022(10) 0.0110(9) 0.0053(10)
C10 0.0348(11) 0.0517(14) 0.0327(9) 0.0050(9) 0.0097(8) 0.0025(10)
C11 0.0424(13) 0.0603(16) 0.0705(15) 0.0110(13) 0.0154(11) 0.0122(12)
C12 0.0341(13) 0.094(2) 0.0780(17) 0.0152(17) 0.0138(12) 0.0135(14)
C13 0.0362(13) 0.091(2) 0.0632(15) -0.0009(15) 0.0124(11) -0.0100(14)
C14 0.0477(14) 0.0637(17) 0.0585(14) -0.0053(12) 0.0161(11) -0.0080(13)

_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
O1W H1W1 0.864(9) . ?
O1W H1W2 0.864(9) . ?
O1 N5 1.246(3) . ?
O2W H2W1 0.86(3) . ?
O2W H2W2 0.86(3) . ?
O2 N5 1.244(2) . ?
O3 N5 1.231(2) . ?
O4 N6 1.238(2) . ?
O5 N6 1.243(2) . ?
O6 N6 1.244(2) . ?
N1 C5 1.351(3) . ?
N1 C1 1.372(3) . ?
N2 C6 1.474(3) . ?
N2 C7 1.486(2) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
N3 C8 1.485(2) . ?
N3 C9 1.482(3) . ?
N3 H3N1 0.86(3) . ?
N3 H3N2 0.86(3) . ?
N4 C10 1.329(3) . ?
N4 C14 1.341(3) . ?
C1 C2 1.352(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.323(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.509(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.501(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.384(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
H1W1 O1W H1W2 106.9(14) . . ?
H2W1 O2W H2W2 106.3(13) . . ?
C5 N1 C1 117.3(2) . . ?
C6 N2 C7 111.36(15) . . ?
C6 N2 H2N1 110.7(14) . . ?
C7 N2 H2N1 109.2(14) . . ?
C6 N2 H2N2 109.5(14) . . ?
C7 N2 H2N2 108.4(15) . . ?
H2N1 N2 H2N2 107.6(13) . . ?
C8 N3 C9 112.09(16) . . ?
C8 N3 H3N1 110.3(14) . . ?
C9 N3 H3N1 108.5(15) . . ?
C8 N3 H3N2 108.4(15) . . ?
C9 N3 H3N2 109.6(15) . . ?
H3N1 N3 H3N2 107.9(13) . . ?
C10 N4 C14 116.78(19) . . ?
O3 N5 O2 121.5(2) . . ?
O3 N5 O1 121.0(2) . . ?
O2 N5 O1 117.49(17) . . ?
O4 N6 O5 119.88(16) . . ?
O4 N6 O6 120.11(19) . . ?
O5 N6 O6 120.01(18) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.30(19) . . ?
N1 C5 C6 115.38(19) . . ?
C4 C5 C6 121.32(18) . . ?
N2 C6 C5 113.48(17) . . ?
N2 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C8 110.05(16) . . ?
N2 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C7 110.14(17) . . ?
N3 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 C10 111.88(18) . . ?
N3 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N3 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N4 C10 C11 123.4(2) . . ?
N4 C10 C9 117.21(18) . . ?
C11 C10 C9 119.4(2) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 118.4(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
N4 C14 C13 123.9(3) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?

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
C5 N1 C1 C2 -0.6(4) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C1 N1 C5 C4 1.0(3) . . . . ?
C1 N1 C5 C6 -179.0(2) . . . . ?
C3 C4 C5 N1 -0.8(3) . . . . ?
C3 C4 C5 C6 179.3(2) . . . . ?
C7 N2 C6 C5 169.35(15) . . . . ?
N1 C5 C6 N2 -173.64(18) . . . . ?
C4 C5 C6 N2 6.3(3) . . . . ?
C6 N2 C7 C8 177.00(15) . . . . ?
C9 N3 C8 C7 -178.23(15) . . . . ?
N2 C7 C8 N3 176.46(14) . . . . ?
C8 N3 C9 C10 -179.27(15) . . . . ?
C14 N4 C10 C11 -1.7(3) . . . . ?
C14 N4 C10 C9 177.60(17) . . . . ?
N3 C9 C10 N4 4.7(2) . . . . ?
N3 C9 C10 C11 -175.99(17) . . . . ?
N4 C10 C11 C12 1.7(3) . . . . ?
C9 C10 C11 C12 -177.6(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C10 N4 C14 C13 0.4(3) . . . . ?
C12 C13 C14 N4 0.8(4) . . . . ?

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
O1W H1W1 O1 0.86(3) 1.912(10) 2.776(2) 179(2) 4_576
O1W H1W2 O2W 0.86(3) 2.017(11) 2.873(2) 171(3) 2_645
O2W H2W1 O6 0.86(3) 1.992(11) 2.816(2) 160(2) 3_675
O2W H2W2 O5 0.86(3) 1.943(10) 2.787(2) 164(2) 4_576
N2 H2N1 O2 0.86(3) 2.056(12) 2.896(2) 163(2) .
N2 H2N1 O1 0.86(3) 2.327(14) 2.986(2) 132.9(16) .
N2 H2N2 O1W 0.86(3) 1.888(9) 2.747(2) 173(2) .
N3 H3N1 O2W 0.86(3) 2.002(10) 2.852(2) 168(2) .
N3 H3N2 O4 0.86(3) 2.037(10) 2.885(2) 166.0(19) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 996132'
#######################################################################
#
#                 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_complex6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(Cl O4), 2(H2 O)'
_chemical_formula_sum            'C14 H24 Cl2 N4 O10'
_chemical_formula_weight         479.27

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'
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                   7.6857(15)
_cell_length_b                   8.7364(17)
_cell_length_c                   8.8059(18)
_cell_angle_alpha                112.20(3)
_cell_angle_beta                 102.88(3)
_cell_angle_gamma                96.14(3)
_cell_volume                     521.58(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1470
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      24.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             250
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9261
_exptl_absorpt_correction_T_max  0.9499
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4024
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1828
_reflns_number_gt                1579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and O atoms, N and H atoms, as well as O and H atoms. 
 Such restraint was mainly employed to define an appropriate geometry for 
 the -NH₂ groups and water molecules.
;

_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)+(0.1228P)²+0.3130P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1828
_refine_ls_number_parameters     148
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1981
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.17035(11) 0.78957(11) -0.01966(10) 0.0532(4) Uani 1 1 d . . .
O1W O 0.6952(4) 0.7991(5) 0.1152(5) 0.0848(10) Uani 1 1 d D . .
H1W1 H 0.629(7) 0.859(6) 0.168(7) 0.127 Uiso 1 1 d D . .
H1W2 H 0.758(7) 0.858(6) 0.080(8) 0.127 Uiso 1 1 d D . .
O1 O 1.3322(8) 0.9036(9) 0.0447(9) 0.198(3) Uani 1 1 d . . .
O2 O 1.0670(9) 0.8044(9) -0.1591(7) 0.174(2) Uani 1 1 d . . .
O3 O 1.0920(7) 0.8174(6) 0.1125(6) 0.1252(16) Uani 1 1 d . . .
O4 O 1.2062(10) 0.6273(6) -0.0751(6) 0.155(2) Uani 1 1 d . . .
N1 N 0.2619(3) 0.6924(3) 0.4284(4) 0.0449(7) Uani 1 1 d . . .
N2 N 0.9128(3) 0.7645(3) 0.3995(3) 0.0346(6) Uani 1 1 d D . .
H2N1 H 0.853(4) 0.761(4) 0.303(2) 0.052 Uiso 1 1 d D . .
H2N2 H 1.013(3) 0.733(4) 0.389(4) 0.052 Uiso 1 1 d D . .
C1 C 0.3980(4) 0.7711(4) 0.5745(4) 0.0470(8) Uani 1 1 d . . .
H1 H 0.3702 0.8387 0.6727 0.056 Uiso 1 1 calc R . .
C2 C 0.5755(4) 0.7570(4) 0.5866(4) 0.0425(7) Uani 1 1 d . . .
H2 H 0.6652 0.8128 0.6909 0.051 Uiso 1 1 calc R . .
C3 C 0.6202(3) 0.6584(3) 0.4410(4) 0.0328(6) Uani 1 1 d . . .
C4 C 0.4802(4) 0.5762(4) 0.2903(4) 0.0403(7) Uani 1 1 d . . .
H4 H 0.5043 0.5081 0.1902 0.048 Uiso 1 1 calc R . .
C5 C 0.3050(4) 0.5960(4) 0.2898(4) 0.0441(7) Uani 1 1 d . . .
H5 H 0.2122 0.5393 0.1877 0.053 Uiso 1 1 calc R . .
C6 C 0.8135(4) 0.6396(4) 0.4474(4) 0.0390(7) Uani 1 1 d . . .
H6A H 0.8127 0.5257 0.3696 0.047 Uiso 1 1 calc R . .
H6B H 0.8784 0.6558 0.5621 0.047 Uiso 1 1 calc R . .
C7 C 0.9410(4) 0.9427(3) 0.5238(4) 0.0381(7) Uani 1 1 d . . .
H7A H 0.9999 0.9542 0.6382 0.046 Uiso 1 1 calc R . .
H7B H 0.8240 0.9749 0.5230 0.046 Uiso 1 1 calc R . .

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 0.0539(6) 0.0631(6) 0.0399(5) 0.0191(4) 0.0117(4) 0.0137(4)
O1W 0.0664(19) 0.117(3) 0.080(2) 0.062(2) 0.0057(16) 0.0064(17)
O1 0.114(4) 0.189(6) 0.185(6) -0.009(4) 0.038(4) -0.058(4)
O2 0.190(5) 0.244(7) 0.103(3) 0.102(4) -0.003(4) 0.085(5)
O3 0.189(4) 0.143(4) 0.118(3) 0.077(3) 0.114(3) 0.098(3)
O4 0.282(7) 0.127(4) 0.114(3) 0.056(3) 0.121(4) 0.118(4)
N1 0.0318(13) 0.0512(15) 0.0608(17) 0.0276(13) 0.0203(12) 0.0138(11)
N2 0.0252(11) 0.0392(13) 0.0413(13) 0.0165(11) 0.0128(10) 0.0083(9)
C1 0.0414(16) 0.0496(18) 0.0518(19) 0.0158(15) 0.0248(15) 0.0125(14)
C2 0.0382(15) 0.0457(17) 0.0402(16) 0.0147(13) 0.0121(13) 0.0049(12)
C3 0.0277(13) 0.0298(13) 0.0432(15) 0.0163(11) 0.0130(11) 0.0049(10)
C4 0.0329(14) 0.0446(16) 0.0417(16) 0.0141(13) 0.0143(12) 0.0081(12)
C5 0.0301(14) 0.0522(18) 0.0479(17) 0.0224(14) 0.0065(13) 0.0031(12)
C6 0.0309(14) 0.0373(15) 0.0540(18) 0.0223(14) 0.0146(13) 0.0098(11)
C7 0.0344(14) 0.0376(15) 0.0451(16) 0.0172(13) 0.0163(13) 0.0073(11)

_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 O1 1.362(5) . ?
Cl1 O2 1.365(4) . ?
Cl1 O3 1.381(3) . ?
Cl1 O4 1.395(4) . ?
O1W H1W1 0.86(5) . ?
O1W H1W2 0.86(5) . ?
N1 C5 1.332(4) . ?
N1 C1 1.342(4) . ?
N2 C7 1.484(4) . ?
N2 C6 1.505(4) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.367(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 C6 1.503(4) . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.514(5) 2_776 ?
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
O1 Cl1 O2 109.2(5) . . ?
O1 Cl1 O3 107.1(4) . . ?
O2 Cl1 O3 114.9(4) . . ?
O1 Cl1 O4 108.4(5) . . ?
O2 Cl1 O4 107.5(4) . . ?
O3 Cl1 O4 109.6(3) . . ?
H1W1 O1W H1W2 108.6(17) . . ?
C5 N1 C1 117.2(2) . . ?
C7 N2 C6 113.3(2) . . ?
C7 N2 H2N1 105(2) . . ?
C6 N2 H2N1 112(2) . . ?
C7 N2 H2N2 113(2) . . ?
C6 N2 H2N2 105(2) . . ?
H2N1 N2 H2N2 108.0(16) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 C6 121.1(3) . . ?
C2 C3 C6 121.2(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.2(3) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C3 C6 N2 112.1(2) . . ?
C3 C6 H6A 109.2 . . ?
N2 C6 H6A 109.2 . . ?
C3 C6 H6B 109.2 . . ?
N2 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C7 109.6(3) . 2_776 ?
N2 C7 H7A 109.7 . . ?
C7 C7 H7A 109.7 2_776 . ?
N2 C7 H7B 109.7 . . ?
C7 C7 H7B 109.7 2_776 . ?
H7A C7 H7B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(5) . . . . ?
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C3 C6 179.7(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C6 C3 C4 C5 179.7(3) . . . . ?
C1 N1 C5 C4 -0.8(5) . . . . ?
C3 C4 C5 N1 0.4(5) . . . . ?
C4 C3 C6 N2 86.5(3) . . . . ?
C2 C3 C6 N2 -94.4(3) . . . . ?
C7 N2 C6 C3 65.8(3) . . . . ?
C6 N2 C7 C7 173.9(3) . . . 2_776 ?

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
O1W H1W1 O1 0.86(5) 2.44(5) 3.033(8) 127(6) 1_455
N2 H2N1 O1W 0.86(3) 1.984(12) 2.824(4) 166(3) .
N2 H2N2 N1 0.86(3) 1.962(12) 2.799(3) 165(3) 1_655

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 996133'
#######################################################################
#
#                 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_complex7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(Cl O4)'
_chemical_formula_sum            'C14 H20 Cl2 N4 O8'
_chemical_formula_weight         443.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   9.7044(19)
_cell_length_b                   8.7674(18)
_cell_length_c                   11.111(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.31(3)
_cell_angle_gamma                90.00
_cell_volume                     902.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3974
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9367
_exptl_absorpt_correction_T_max  0.9443
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8692
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2070
_reflns_number_gt                1216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group.
;

_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)+(0.1181P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2070
_refine_ls_number_parameters     133
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.2042
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 1.67646(9) 0.96974(8) 1.21018(7) 0.0462(3) Uani 1 1 d . . .
O1 O 1.8160(3) 1.0275(4) 1.2693(3) 0.0786(9) Uani 1 1 d . . .
O2 O 1.5788(3) 1.0951(3) 1.1778(3) 0.0707(8) Uani 1 1 d . . .
O3 O 1.6788(4) 0.8875(3) 1.1016(3) 0.0808(9) Uani 1 1 d . . .
O4 O 1.6314(4) 0.8705(3) 1.2925(3) 0.0867(10) Uani 1 1 d . . .
N1 N 1.2000(3) 0.7239(3) 0.9781(2) 0.0487(7) Uani 1 1 d . . .
N2 N 1.3629(3) 0.9326(3) 1.3511(2) 0.0400(6) Uani 1 1 d D . .
H2N1 H 1.421(3) 0.878(3) 1.326(3) 0.060 Uiso 1 1 d D . .
H2N2 H 1.315(3) 0.877(3) 1.388(3) 0.060 Uiso 1 1 d D . .
C1 C 1.2595(4) 0.8276(3) 1.0658(3) 0.0446(8) Uani 1 1 d . . .
H1 H 1.3555 0.8535 1.0774 0.053 Uiso 1 1 calc R . .
C2 C 1.1885(3) 0.8990(3) 1.1403(3) 0.0413(7) Uani 1 1 d . . .
C3 C 1.0428(4) 0.8646(4) 1.1172(3) 0.0487(8) Uani 1 1 d . . .
H3 H 0.9893 0.9117 1.1636 0.058 Uiso 1 1 calc R . .
C4 C 0.9790(4) 0.7604(4) 1.0251(3) 0.0543(9) Uani 1 1 d . . .
H4 H 0.8815 0.7368 1.0074 0.065 Uiso 1 1 calc R . .
C5 C 1.0607(4) 0.6928(4) 0.9604(3) 0.0549(9) Uani 1 1 d . . .
H5 H 1.0171 0.6202 0.8999 0.066 Uiso 1 1 calc R . .
C6 C 1.2649(4) 1.0119(3) 1.2391(3) 0.0456(8) Uani 1 1 d . . .
H6A H 1.3208 1.0813 1.2041 0.055 Uiso 1 1 calc R . .
H6B H 1.1944 1.0714 1.2651 0.055 Uiso 1 1 calc R . .
C7 C 1.4482(4) 1.0419(3) 1.4457(3) 0.0443(8) Uani 1 1 d . . .
H7A H 1.3836 1.1041 1.4771 0.053 Uiso 1 1 calc R . .
H7B H 1.5018 1.1089 1.4065 0.053 Uiso 1 1 calc R . .

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 0.0445(6) 0.0428(5) 0.0527(6) -0.0018(3) 0.0165(4) 0.0002(3)
O1 0.0451(18) 0.093(2) 0.087(2) -0.0207(15) 0.0030(15) -0.0050(14)
O2 0.0569(18) 0.0533(14) 0.099(2) 0.0136(15) 0.0194(15) 0.0135(12)
O3 0.111(3) 0.0684(17) 0.0690(18) -0.0268(14) 0.0367(17) -0.0123(16)
O4 0.113(3) 0.0669(16) 0.109(2) 0.0333(17) 0.078(2) 0.0229(17)
N1 0.0542(19) 0.0544(16) 0.0359(14) -0.0064(11) 0.0110(12) -0.0014(13)
N2 0.0437(16) 0.0373(12) 0.0386(14) -0.0017(11) 0.0119(11) 0.0020(11)
C1 0.0396(18) 0.0479(17) 0.0447(17) 0.0020(14) 0.0105(14) 0.0011(13)
C2 0.0445(19) 0.0416(16) 0.0372(16) 0.0040(13) 0.0114(13) 0.0014(13)
C3 0.0425(19) 0.0565(19) 0.0468(18) 0.0022(15) 0.0127(14) 0.0067(15)
C4 0.041(2) 0.063(2) 0.053(2) 0.0000(16) 0.0058(15) -0.0049(15)
C5 0.060(2) 0.058(2) 0.0397(17) -0.0035(15) 0.0045(15) -0.0088(17)
C6 0.051(2) 0.0410(16) 0.0415(17) 0.0016(13) 0.0087(16) 0.0037(14)
C7 0.049(2) 0.0416(17) 0.0390(17) -0.0061(12) 0.0080(14) -0.0004(13)

_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 O1 1.411(3) . ?
Cl1 O3 1.411(3) . ?
Cl1 O4 1.422(3) . ?
Cl1 O2 1.426(2) . ?
N1 C1 1.332(4) . ?
N1 C5 1.335(4) . ?
N2 C7 1.480(4) . ?
N2 C6 1.494(4) . ?
N2 H2N1 0.85(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(5) . ?
C2 C6 1.500(4) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.511(6) 3_878 ?
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
O1 Cl1 O3 108.9(2) . . ?
O1 Cl1 O4 110.9(2) . . ?
O3 Cl1 O4 108.86(18) . . ?
O1 Cl1 O2 108.34(18) . . ?
O3 Cl1 O2 110.90(19) . . ?
O4 Cl1 O2 109.00(17) . . ?
C1 N1 C5 116.5(3) . . ?
C7 N2 C6 111.9(2) . . ?
C7 N2 H2N1 108(3) . . ?
C6 N2 H2N1 108(2) . . ?
C7 N2 H2N2 107(2) . . ?
C6 N2 H2N2 111(2) . . ?
H2N1 N2 H2N2 109.9(16) . . ?
N1 C1 C2 124.4(3) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 116.9(3) . . ?
C1 C2 C6 120.9(3) . . ?
C3 C2 C6 122.1(3) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 124.0(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N2 C6 C2 110.8(2) . . ?
N2 C6 H6A 109.5 . . ?
C2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 110.5(3) . 3_878 ?
N2 C7 H7A 109.5 . . ?
C7 C7 H7A 109.5 3_878 . ?
N2 C7 H7B 109.5 . . ?
C7 C7 H7B 109.5 3_878 . ?
H7A C7 H7B 108.1 . . ?

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
C5 N1 C1 C2 2.2(5) . . . . ?
N1 C1 C2 C3 -3.2(5) . . . . ?
N1 C1 C2 C6 178.5(3) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C6 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C1 N1 C5 C4 0.4(5) . . . . ?
C3 C4 C5 N1 -1.9(5) . . . . ?
C7 N2 C6 C2 175.5(3) . . . . ?
C1 C2 C6 N2 -75.4(4) . . . . ?
C3 C2 C6 N2 106.4(3) . . . . ?
C6 N2 C7 C7 -176.9(3) . . . 3_878 ?

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
N2 H2N1 O4 0.85(3) 2.180(19) 2.919(4) 145(3) .
N2 H2N1 O2 0.85(3) 2.48(3) 3.047(3) 125(2) 2_847
N2 H2N2 N1 0.86(3) 1.924(10) 2.775(4) 173(3) 4_576

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 996134'
#######################################################################
#
#                 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_complex8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4, 2(Cl O4)'
_chemical_formula_sum            'C14 H20 Cl2 N4 O8'
_chemical_formula_weight         443.24

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'
O O 0.0106 0.0060 '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                   9.1173(5)
_cell_length_b                   9.3303(5)
_cell_length_c                   12.6102(11)
_cell_angle_alpha                105.576(6)
_cell_angle_beta                 105.569(6)
_cell_angle_gamma                98.003(4)
_cell_volume                     969.25(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1463
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9200
_exptl_absorpt_correction_T_max  0.9409
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5263
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3332
_reflns_number_gt                2228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 For the H₂M3²⁺ cation in this salt, DFIX, EADP and EXYZ were used to 
 refine the disorder of the protonated ethylenediamine units.
;

_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)+(0.1442P)²+0.0000P] 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         3332
_refine_ls_number_parameters     256
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2401
_refine_ls_wR_factor_gt          0.2091
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.063
_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 0.74525(13) -0.07618(14) -0.36677(11) 0.0792(5) Uani 1 1 d . . .
Cl2 Cl 0.59383(14) 0.38054(18) 0.18454(13) 0.0929(5) Uani 1 1 d . . .
O1 O 0.6261(6) -0.0934(9) -0.3247(6) 0.195(4) Uani 1 1 d . . .
O2 O 0.8705(7) -0.0951(9) -0.2790(6) 0.179(3) Uani 1 1 d . . .
O3 O 0.8182(13) 0.0635(6) -0.3650(6) 0.209(4) Uani 1 1 d . . .
O4 O 0.7244(5) -0.1924(5) -0.4719(4) 0.1086(13) Uani 1 1 d . . .
O5 O 0.6737(13) 0.4585(10) 0.1240(9) 0.228(4) Uani 1 1 d . . .
O6 O 0.5204(8) 0.2307(7) 0.1102(7) 0.180(3) Uani 1 1 d . . .
O7 O 0.7056(13) 0.3670(19) 0.2666(11) 0.318(8) Uani 1 1 d . . .
O8 O 0.4900(10) 0.4462(10) 0.2177(12) 0.278(6) Uani 1 1 d . . .
N1 N 0.3186(4) -0.2739(4) -0.4852(3) 0.0657(9) Uani 1 1 d . . .
N2 N 0.2796(6) -0.0205(8) -0.3479(7) 0.205(5) Uani 1 1 d D . .
H2N1 H 0.2973 0.0231 -0.3967 0.246 Uiso 1 1 d R A .
H2N2 H 0.3581 -0.0585 -0.3243 0.246 Uiso 1 1 d R . .
N3 N 0.5417(7) 0.1383(10) -0.1494(5) 0.180(4) Uani 0.50 1 d PD A 1
H3N1 H 0.5357 0.0508 -0.1973 0.216 Uiso 0.50 1 d PR A 1
H3N2 H 0.5495 0.1293 -0.0822 0.216 Uiso 0.50 1 d PR A 1
N3' N 0.5417(7) 0.1383(10) -0.1494(5) 0.180(4) Uani 0.50 1 d P A 2
H3'A H 0.5267 0.0734 -0.2164 0.216 Uiso 0.50 1 d PR A 2
H3'B H 0.5894 0.0974 -0.1008 0.216 Uiso 0.50 1 d PR A 2
N4 N 0.8252(6) 0.1680(6) -0.0034(5) 0.0948(14) Uani 1 1 d . . .
C1 C 0.3589(6) -0.3857(6) -0.5579(4) 0.0764(13) Uani 1 1 d . . .
H1A H 0.4637 -0.3849 -0.5487 0.092 Uiso 1 1 calc R . .
C2 C 0.2461(7) -0.4981(6) -0.6435(5) 0.0926(16) Uani 1 1 d . . .
H2A H 0.2708 -0.5753 -0.6952 0.111 Uiso 1 1 calc R . .
C3 C 0.0939(6) -0.4942(6) -0.6516(5) 0.0874(15) Uani 1 1 d . . .
H3A H 0.0141 -0.5708 -0.7098 0.105 Uiso 1 1 calc R . .
C4 C 0.0552(6) -0.3798(6) -0.5757(4) 0.0827(14) Uani 1 1 d . . .
H4A H -0.0489 -0.3790 -0.5829 0.099 Uiso 1 1 calc R . .
C5 C 0.1730(5) -0.2679(5) -0.4900(4) 0.0662(11) Uani 1 1 d . . .
C6 C 0.1482(5) -0.1344(6) -0.4012(5) 0.0956(18) Uani 1 1 d D . .
H6A H 0.0640 -0.0946 -0.4399 0.115 Uiso 1 1 calc R . .
H6B H 0.1175 -0.1702 -0.3432 0.115 Uiso 1 1 calc R . .
C7 C 0.2627(7) 0.0940(9) -0.2478(8) 0.162(4) Uani 0.50 1 d PD A 1
H7A H 0.1811 0.1450 -0.2742 0.194 Uiso 0.50 1 calc PR A 1
H7B H 0.2350 0.0448 -0.1949 0.194 Uiso 0.50 1 calc PR A 1
C7' C 0.2627(7) 0.0940(9) -0.2478(8) 0.162(4) Uani 0.50 1 d P A 2
H7'A H 0.2681 0.1919 -0.2612 0.194 Uiso 0.50 1 calc PR A 2
H7'B H 0.1617 0.0628 -0.2392 0.194 Uiso 0.50 1 calc PR A 2
C8 C 0.4082(9) 0.2012(13) -0.1908(12) 0.127(4) Uani 0.50 1 d PD A 1
H8A H 0.3986 0.2773 -0.1250 0.152 Uiso 0.50 1 calc PR A 1
H8B H 0.4296 0.2531 -0.2440 0.152 Uiso 0.50 1 calc PR A 1
C8' C 0.3884(12) 0.1090(18) -0.1405(10) 0.127(4) Uani 0.50 1 d PD A 2
H8'A H 0.3818 0.1916 -0.0773 0.152 Uiso 0.50 1 calc PR A 2
H8'B H 0.3715 0.0155 -0.1211 0.152 Uiso 0.50 1 calc PR A 2
C9 C 0.6697(9) 0.2512(10) -0.1440(8) 0.174(5) Uani 1 1 d D . .
H9A H 0.6537 0.3516 -0.1096 0.209 Uiso 1 1 calc R A 1
H9B H 0.6687 0.2424 -0.2226 0.209 Uiso 1 1 calc R A 1
C10 C 0.8240(8) 0.2403(8) -0.0775(6) 0.110(2) Uani 1 1 d D A .
C11 C 0.9597(16) 0.3155(8) -0.0912(8) 0.143(3) Uani 1 1 d . . .
H11A H 0.9545 0.3678 -0.1448 0.172 Uiso 1 1 calc R A .
C12 C 1.1030(8) 0.3066(8) -0.0192(9) 0.125(3) Uani 1 1 d . A .
H12A H 1.1971 0.3531 -0.0239 0.150 Uiso 1 1 calc R . .
C13 C 1.1013(7) 0.2308(8) 0.0554(7) 0.105(2) Uani 1 1 d . . .
H13A H 1.1941 0.2236 0.1048 0.126 Uiso 1 1 calc R A .
C14 C 0.9608(7) 0.1638(7) 0.0582(6) 0.1046(19) Uani 1 1 d . A .
H14A H 0.9632 0.1091 0.1101 0.126 Uiso 1 1 calc R . .

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 0.0634(7) 0.0774(8) 0.0916(9) 0.0123(6) 0.0322(6) 0.0148(5)
Cl2 0.0560(7) 0.1226(12) 0.0964(10) 0.0284(8) 0.0250(6) 0.0211(7)
O1 0.087(3) 0.251(7) 0.163(5) -0.072(5) 0.071(3) -0.021(4)
O2 0.122(4) 0.240(7) 0.143(5) 0.044(5) -0.010(4) 0.075(5)
O3 0.372(13) 0.095(4) 0.141(5) 0.032(3) 0.075(6) 0.020(5)
O4 0.098(3) 0.105(3) 0.107(3) 0.000(2) 0.049(2) 0.008(2)
O5 0.275(11) 0.204(7) 0.292(10) 0.109(7) 0.194(9) 0.066(7)
O6 0.129(4) 0.132(4) 0.234(7) 0.000(4) 0.064(5) -0.007(3)
O7 0.168(8) 0.50(2) 0.261(11) 0.223(13) -0.040(7) -0.003(10)
O8 0.162(7) 0.193(6) 0.496(17) 0.038(9) 0.196(10) 0.059(5)
N1 0.0490(18) 0.073(2) 0.067(2) 0.0113(17) 0.0181(15) 0.0145(15)
N2 0.071(3) 0.192(6) 0.212(7) -0.127(6) 0.008(4) 0.041(4)
N3 0.094(4) 0.305(10) 0.087(4) -0.030(5) 0.001(3) 0.113(6)
N3' 0.094(4) 0.305(10) 0.087(4) -0.030(5) 0.001(3) 0.113(6)
N4 0.072(3) 0.091(3) 0.098(3) 0.002(3) 0.017(2) 0.021(2)
C1 0.068(3) 0.081(3) 0.076(3) 0.015(2) 0.025(2) 0.020(2)
C2 0.106(4) 0.080(3) 0.087(4) 0.013(3) 0.038(3) 0.020(3)
C3 0.081(3) 0.078(3) 0.074(3) 0.000(3) 0.017(3) -0.010(2)
C4 0.063(3) 0.097(3) 0.083(3) 0.027(3) 0.022(2) 0.008(2)
C5 0.051(2) 0.077(3) 0.070(3) 0.019(2) 0.0245(19) 0.0123(18)
C6 0.056(3) 0.104(4) 0.106(4) -0.003(3) 0.028(3) 0.024(2)
C7 0.062(3) 0.172(7) 0.158(7) -0.075(6) 0.010(4) 0.033(4)
C7' 0.062(3) 0.172(7) 0.158(7) -0.075(6) 0.010(4) 0.033(4)
C8 0.144(9) 0.140(10) 0.108(8) 0.024(6) 0.049(7) 0.078(8)
C8' 0.144(9) 0.140(10) 0.108(8) 0.024(6) 0.049(7) 0.078(8)
C9 0.132(7) 0.169(8) 0.147(7) -0.015(6) -0.035(6) 0.088(6)
C10 0.104(5) 0.097(5) 0.094(5) -0.020(4) 0.020(4) 0.034(4)
C11 0.228(12) 0.077(4) 0.132(6) 0.006(4) 0.097(8) 0.036(6)
C12 0.074(4) 0.095(5) 0.157(7) -0.037(5) 0.039(4) 0.013(3)
C13 0.072(4) 0.092(4) 0.125(5) -0.003(4) 0.028(3) 0.020(3)
C14 0.084(4) 0.105(4) 0.102(4) 0.007(3) 0.020(3) 0.021(3)

_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 O1 1.339(5) . ?
Cl1 O3 1.369(7) . ?
Cl1 O4 1.416(4) . ?
Cl1 O2 1.429(6) . ?
Cl2 O7 1.290(9) . ?
Cl2 O8 1.297(7) . ?
Cl2 O6 1.407(6) . ?
Cl2 O5 1.446(8) . ?
N1 C5 1.323(5) . ?
N1 C1 1.355(6) . ?
N2 C6 1.358(6) . ?
N2 C7 1.478(8) . ?
N2 H2N1 0.8601 . ?
N2 H2N2 0.8600 . ?
N3 C9 1.432(9) . ?
N3 C8 1.456(8) . ?
N3 H3N1 0.8600 . ?
N3 H3N2 0.8600 . ?
N3 H3'A 0.8600 . ?
N3 H3'B 0.8600 . ?
N4 C14 1.284(8) . ?
N4 C10 1.289(10) . ?
C1 C2 1.349(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.523(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.417(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C9 C10 1.464(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.411(12) . ?
C11 C12 1.404(13) . ?
C11 H11A 0.9300 . ?
C12 C13 1.322(11) . ?
C12 H12A 0.9300 . ?
C13 C14 1.358(10) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

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
O1 Cl1 O3 122.3(6) . . ?
O1 Cl1 O4 113.4(3) . . ?
O3 Cl1 O4 112.0(4) . . ?
O1 Cl1 O2 101.9(5) . . ?
O3 Cl1 O2 96.7(5) . . ?
O4 Cl1 O2 107.3(4) . . ?
O7 Cl2 O8 115.5(10) . . ?
O7 Cl2 O6 105.7(8) . . ?
O8 Cl2 O6 109.0(5) . . ?
O7 Cl2 O5 104.0(8) . . ?
O8 Cl2 O5 114.0(7) . . ?
O6 Cl2 O5 108.2(5) . . ?
C5 N1 C1 124.3(4) . . ?
C6 N2 C7 110.8(6) . . ?
C6 N2 H2N1 109.5 . . ?
C7 N2 H2N1 109.5 . . ?
C6 N2 H2N2 109.4 . . ?
C7 N2 H2N2 109.5 . . ?
H2N1 N2 H2N2 108.1 . . ?
C9 N3 C8 102.0(7) . . ?
C9 N3 H3N1 111.3 . . ?
C8 N3 H3N1 111.3 . . ?
C9 N3 H3N2 111.4 . . ?
C8 N3 H3N2 111.4 . . ?
H3N1 N3 H3N2 109.2 . . ?
C9 N3 H3'A 100.2 . . ?
C8 N3 H3'A 94.0 . . ?
H3N2 N3 H3'A 133.1 . . ?
C9 N3 H3'B 100.3 . . ?
C8 N3 H3'B 148.1 . . ?
H3N1 N3 H3'B 80.9 . . ?
H3'A N3 H3'B 104.3 . . ?
C14 N4 C10 115.8(6) . . ?
C2 C1 N1 119.6(4) . . ?
C2 C1 H1A 120.2 . . ?
N1 C1 H1A 120.2 . . ?
C1 C2 C3 117.5(5) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 H2A 121.3 . . ?
C2 C3 C4 122.0(4) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 118.7(5) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
N1 C5 C4 117.8(4) . . ?
N1 C5 C6 117.6(4) . . ?
C4 C5 C6 124.5(4) . . ?
N2 C6 C5 111.8(4) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 N2 107.5(8) . . ?
C8 C7 H7A 110.2 . . ?
N2 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
N2 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 N3 115.7(8) . . ?
C7 C8 H8A 108.4 . . ?
N3 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
N3 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
H3N2 C8' H8'A 90.3 . . ?
H3N2 C8' H8'B 87.3 . . ?
H8'A C8' H8'B 107.7 . . ?
N3 C9 C10 114.8(7) . . ?
N3 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
N4 C10 C11 124.2(7) . . ?
N4 C10 C9 115.8(8) . . ?
C11 C10 C9 119.9(10) . . ?
C12 C11 C10 116.1(8) . . ?
C12 C11 H11A 121.9 . . ?
C10 C11 H11A 121.9 . . ?
C13 C12 C11 118.5(8) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C12 C13 C14 118.5(7) . . ?
C12 C13 H13A 120.8 . . ?
C14 C13 H13A 120.8 . . ?
N4 C14 C13 126.8(8) . . ?
N4 C14 H14A 116.6 . . ?
C13 C14 H14A 116.6 . . ?

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
C5 N1 C1 C2 1.7(8) . . . . ?
N1 C1 C2 C3 -0.9(8) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C1 N1 C5 C4 -1.7(7) . . . . ?
C1 N1 C5 C6 179.8(5) . . . . ?
C3 C4 C5 N1 1.0(7) . . . . ?
C3 C4 C5 C6 179.4(5) . . . . ?
C7 N2 C6 C5 -169.4(7) . . . . ?
N1 C5 C6 N2 15.2(9) . . . . ?
C4 C5 C6 N2 -163.2(7) . . . . ?
C6 N2 C7 C8 175.0(10) . . . . ?
N2 C7 C8 N3 -58.4(14) . . . . ?
C9 N3 C8 C7 156.4(11) . . . . ?
C8 N3 C9 C10 165.2(8) . . . . ?
C14 N4 C10 C11 -1.7(8) . . . . ?
C14 N4 C10 C9 -177.3(5) . . . . ?
N3 C9 C10 N4 -21.3(9) . . . . ?
N3 C9 C10 C11 162.9(6) . . . . ?
N4 C10 C11 C12 0.9(9) . . . . ?
C9 C10 C11 C12 176.4(6) . . . . ?
C10 C11 C12 C13 -0.3(9) . . . . ?
C11 C12 C13 C14 0.6(9) . . . . ?
C10 N4 C14 C13 2.0(9) . . . . ?
C12 C13 C14 N4 -1.5(10) . . . . ?

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
N2 H2N1 O4 0.86 2.57 3.393(12) 160.9 2_654
N2 H2N2 O1 0.86 2.51 3.277(8) 148.9 .
N3 H3N1 O1 0.86 2.22 2.994(7) 149.6 .
N3 H3N2 O6 0.86 2.46 3.220(9) 148.5 .

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 996135'
#######################################################################
#
#                 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_complex9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(Cl)'
_chemical_formula_sum            'C14 H22 Cl4 N4'
_chemical_formula_weight         388.16

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           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                   5.1471(8)
_cell_length_b                   8.9123(14)
_cell_length_c                   11.038(2)
_cell_angle_alpha                113.121(13)
_cell_angle_beta                 97.784(13)
_cell_angle_gamma                91.085(12)
_cell_volume                     459.93(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1505
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      24.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             202
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8712
_exptl_absorpt_correction_T_max  0.9039
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3396
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1604
_reflns_number_gt                1109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.1331P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1604
_refine_ls_number_parameters     109
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1965
_refine_ls_wR_factor_gt          0.1867
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.027
_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 0.6370(2) -0.27562(19) 0.37363(14) 0.0509(6) Uani 1 1 d . . .
Cl2 Cl 1.4828(2) 0.20397(18) -0.02390(13) 0.0444(6) Uani 1 1 d . . .
N1 N 0.8967(8) 0.0081(6) 0.3343(4) 0.0447(13) Uani 1 1 d D . .
H1N H 0.809(9) -0.069(6) 0.342(7) 0.067 Uiso 1 1 d D . .
N2 N 1.0250(7) 0.3767(6) 0.1048(4) 0.0343(11) Uani 1 1 d D . .
H2N1 H 0.875(4) 0.328(5) 0.062(4) 0.051 Uiso 1 1 d D . .
H2N2 H 1.146(6) 0.323(5) 0.065(4) 0.051 Uiso 1 1 d D . .
C1 C 0.7772(10) 0.1416(9) 0.3872(6) 0.0492(17) Uani 1 1 d . . .
H1A H 0.6520 0.1451 0.4414 0.059 Uiso 1 1 calc R . .
C2 C 0.8383(9) 0.2781(7) 0.3620(5) 0.0414(15) Uani 1 1 d . . .
H2A H 0.7577 0.3746 0.4003 0.050 Uiso 1 1 calc R . .
C3 C 1.0214(9) 0.2674(7) 0.2788(5) 0.0360(13) Uani 1 1 d . . .
C4 C 1.1462(9) 0.1269(8) 0.2285(5) 0.0422(15) Uani 1 1 d . . .
H4A H 1.2759 0.1206 0.1760 0.051 Uiso 1 1 calc R . .
C5 C 1.0783(10) -0.0052(7) 0.2562(5) 0.0433(14) Uani 1 1 d . . .
H5A H 1.1583 -0.1025 0.2208 0.052 Uiso 1 1 calc R . .
C6 C 1.0867(10) 0.4164(8) 0.2515(5) 0.0426(15) Uani 1 1 d . . .
H6A H 0.9854 0.5051 0.2997 0.051 Uiso 1 1 calc R . .
H6B H 1.2719 0.4518 0.2825 0.051 Uiso 1 1 calc R . .
C7 C 1.0309(9) 0.5270(7) 0.0760(5) 0.0373(13) Uani 1 1 d . . .
H7A H 1.2032 0.5861 0.1098 0.045 Uiso 1 1 calc R . .
H7B H 0.9013 0.5985 0.1190 0.045 Uiso 1 1 calc R . .

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 0.0559(9) 0.0485(13) 0.0495(9) 0.0167(10) 0.0220(7) -0.0013(7)
Cl2 0.0391(8) 0.0482(12) 0.0432(9) 0.0122(9) 0.0160(6) 0.0059(6)
N1 0.048(2) 0.051(4) 0.035(3) 0.016(3) 0.010(2) -0.008(2)
N2 0.037(2) 0.036(3) 0.031(2) 0.013(3) 0.0093(17) 0.0076(19)
C1 0.049(3) 0.068(5) 0.033(3) 0.019(4) 0.017(2) -0.001(3)
C2 0.042(3) 0.049(4) 0.032(3) 0.011(4) 0.016(2) 0.010(2)
C3 0.041(2) 0.039(4) 0.027(3) 0.012(3) 0.004(2) 0.001(2)
C4 0.048(3) 0.048(4) 0.035(3) 0.017(4) 0.018(2) 0.002(3)
C5 0.054(3) 0.037(4) 0.035(3) 0.008(3) 0.014(2) 0.002(3)
C6 0.053(3) 0.039(4) 0.034(3) 0.013(3) 0.007(2) -0.002(2)
C7 0.046(3) 0.029(4) 0.037(3) 0.012(3) 0.014(2) 0.005(2)

_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 C1 1.309(8) . ?
N1 C5 1.331(6) . ?
N1 H1N 0.86(5) . ?
N2 C7 1.493(6) . ?
N2 C6 1.502(6) . ?
N2 H2N1 0.86(5) . ?
N2 H2N2 0.86(5) . ?
C1 C2 1.390(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(8) . ?
C3 C6 1.514(7) . ?
C4 C5 1.378(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.538(10) 2_765 ?
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
C1 N1 C5 123.3(5) . . ?
C1 N1 H1N 107(5) . . ?
C5 N1 H1N 128(5) . . ?
C7 N2 C6 112.0(4) . . ?
C7 N2 H2N1 103(3) . . ?
C6 N2 H2N1 119(3) . . ?
C7 N2 H2N2 104(3) . . ?
C6 N2 H2N2 110(3) . . ?
H2N1 N2 H2N2 109.0(18) . . ?
N1 C1 C2 119.7(4) . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 C6 121.9(4) . . ?
C2 C3 C6 118.3(5) . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 119.2(5) . . ?
N1 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
N2 C6 C3 110.2(5) . . ?
N2 C6 H6A 109.6 . . ?
C3 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C3 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 107.8(6) . 2_765 ?
N2 C7 H7A 110.1 . . ?
C7 C7 H7A 110.1 2_765 . ?
N2 C7 H7B 110.1 . . ?
C7 C7 H7B 110.1 2_765 . ?
H7A C7 H7B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(8) . . . . ?
N1 C1 C2 C3 1.3(8) . . . . ?
C1 C2 C3 C4 -3.0(7) . . . . ?
C1 C2 C3 C6 179.9(4) . . . . ?
C2 C3 C4 C5 3.1(8) . . . . ?
C6 C3 C4 C5 -179.8(4) . . . . ?
C1 N1 C5 C4 -0.1(8) . . . . ?
C3 C4 C5 N1 -1.6(8) . . . . ?
C7 N2 C6 C3 167.7(4) . . . . ?
C4 C3 C6 N2 62.6(6) . . . . ?
C2 C3 C6 N2 -120.3(5) . . . . ?
C6 N2 C7 C7 179.3(5) . . . 2_765 ?

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
N1 H1N Cl1 0.86(5) 2.192(14) 3.043(5) 172(5) .
N2 H2N1 Cl2 0.86(5) 2.182(12) 3.037(4) 173(4) 1_455
N2 H2N2 Cl2 0.86(5) 2.192(11) 3.044(4) 175(4) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 996136'
#######################################################################
#
#                 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_complex10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(Cl)'
_chemical_formula_sum            'C14 H22 Cl4 N4'
_chemical_formula_weight         388.16

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           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                   5.2162(6)
_cell_length_b                   9.0691(12)
_cell_length_c                   10.8806(10)
_cell_angle_alpha                65.623(11)
_cell_angle_beta                 82.154(9)
_cell_angle_gamma                87.040(10)
_cell_volume                     464.44(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    968
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             202
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8723
_exptl_absorpt_correction_T_max  0.9047
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2746
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         27.56
_reflns_number_total             2119
_reflns_number_gt                1624
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.0483P)²+0.7581P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     109
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_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 0.99618(16) 0.71033(11) 0.51818(10) 0.0473(3) Uani 1 1 d . . .
Cl2 Cl -0.09034(18) 0.79192(11) -0.10391(10) 0.0496(3) Uani 1 1 d . . .
N1 N 0.2750(6) 0.6652(4) 0.1072(3) 0.0440(7) Uani 1 1 d D . .
H1N H 0.165(7) 0.686(5) 0.050(3) 0.066 Uiso 1 1 d D . .
N2 N 0.5195(5) 0.8778(3) 0.3957(3) 0.0326(6) Uani 1 1 d D . .
H2N1 H 0.372(3) 0.829(4) 0.427(3) 0.049 Uiso 1 1 d D . .
H2N2 H 0.637(4) 0.813(3) 0.437(3) 0.049 Uiso 1 1 d D . .
C1 C 0.3310(6) 0.7888(4) 0.1360(3) 0.0389(8) Uani 1 1 d . . .
H1A H 0.2459 0.8870 0.0986 0.047 Uiso 1 1 calc R . .
C2 C 0.5148(6) 0.7710(4) 0.2210(3) 0.0331(7) Uani 1 1 d . . .
C3 C 0.6400(6) 0.6232(4) 0.2724(3) 0.0370(7) Uani 1 1 d . . .
H3A H 0.7660 0.6079 0.3293 0.044 Uiso 1 1 calc R . .
C4 C 0.5786(8) 0.4995(4) 0.2398(4) 0.0462(9) Uani 1 1 d . . .
H4A H 0.6637 0.4008 0.2737 0.055 Uiso 1 1 calc R . .
C5 C 0.3919(8) 0.5223(5) 0.1571(4) 0.0476(9) Uani 1 1 d . . .
H5A H 0.3466 0.4385 0.1359 0.057 Uiso 1 1 calc R . .
C6 C 0.5750(7) 0.9138(4) 0.2481(3) 0.0391(8) Uani 1 1 d . . .
H6A H 0.7561 0.9429 0.2172 0.047 Uiso 1 1 calc R . .
H6B H 0.4721 1.0055 0.1972 0.047 Uiso 1 1 calc R . .
C7 C 0.5236(7) 1.0240(4) 0.4244(3) 0.0379(7) Uani 1 1 d . . .
H7A H 0.3909 1.0989 0.3808 0.045 Uiso 1 1 calc R . .
H7B H 0.6902 1.0780 0.3880 0.045 Uiso 1 1 calc R . .

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 0.0338(4) 0.0482(5) 0.0557(6) -0.0145(4) -0.0144(4) 0.0007(4)
Cl2 0.0509(6) 0.0486(5) 0.0486(5) -0.0142(4) -0.0208(4) -0.0050(4)
N1 0.0399(16) 0.061(2) 0.0377(16) -0.0241(15) -0.0113(13) -0.0055(14)
N2 0.0302(13) 0.0348(14) 0.0372(15) -0.0177(12) -0.0096(11) 0.0009(11)
C1 0.0377(18) 0.046(2) 0.0334(17) -0.0164(15) -0.0083(14) 0.0028(15)
C2 0.0355(16) 0.0382(17) 0.0271(15) -0.0147(13) -0.0029(12) -0.0022(13)
C3 0.0389(17) 0.0409(18) 0.0326(16) -0.0148(14) -0.0095(14) -0.0003(14)
C4 0.061(2) 0.0353(18) 0.041(2) -0.0128(15) -0.0104(17) -0.0022(16)
C5 0.057(2) 0.048(2) 0.043(2) -0.0245(18) -0.0022(17) -0.0148(18)
C6 0.0461(19) 0.0382(18) 0.0325(17) -0.0130(14) -0.0069(15) -0.0028(15)
C7 0.0422(18) 0.0365(18) 0.0425(19) -0.0225(15) -0.0108(15) 0.0034(14)

_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 C5 1.332(5) . ?
N1 C1 1.338(4) . ?
N1 H1N 0.86(3) . ?
N2 C7 1.484(4) . ?
N2 C6 1.490(4) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.380(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(5) . ?
C2 C6 1.498(4) . ?
C3 C4 1.373(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.504(7) 2_676 ?
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
C5 N1 C1 122.5(3) . . ?
C5 N1 H1N 122(3) . . ?
C1 N1 H1N 115(3) . . ?
C7 N2 C6 113.2(3) . . ?
C7 N2 H2N1 111(3) . . ?
C6 N2 H2N1 109(3) . . ?
C7 N2 H2N2 108(3) . . ?
C6 N2 H2N2 108(3) . . ?
H2N1 N2 H2N2 108.0(16) . . ?
N1 C1 C2 120.1(3) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 C6 118.3(3) . . ?
C3 C2 C6 123.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 119.6(3) . . ?
N1 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
N2 C6 C2 111.3(3) . . ?
N2 C6 H6A 109.4 . . ?
C2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C2 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C7 109.6(3) . 2_676 ?
N2 C7 H7A 109.7 . . ?
C7 C7 H7A 109.7 2_676 . ?
N2 C7 H7B 109.7 . . ?
C7 C7 H7B 109.7 2_676 . ?
H7A C7 H7B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.4(5) . . . . ?
N1 C1 C2 C3 1.1(5) . . . . ?
N1 C1 C2 C6 178.8(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C6 C2 C3 C4 -178.2(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C1 N1 C5 C4 -0.8(6) . . . . ?
C3 C4 C5 N1 1.3(6) . . . . ?
C7 N2 C6 C2 -168.1(3) . . . . ?
C1 C2 C6 N2 119.7(3) . . . . ?
C3 C2 C6 N2 -62.8(4) . . . . ?
C6 N2 C7 C7 -177.8(3) . . . 2_676 ?

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
N1 H1N Cl2 0.86(3) 2.153(14) 3.003(3) 168(4) .
N2 H2N1 Cl1 0.86(3) 2.188(11) 3.050(3) 176(4) 1_455
N2 H2N2 Cl1 0.86(3) 2.181(12) 3.018(3) 164(3) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 996137'
#######################################################################
#
#                 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_complex12

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(N O3)'
_chemical_formula_sum            'C14 H22 N8 O12'
_chemical_formula_weight         494.40

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'

_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                   5.7272(11)
_cell_length_b                   9.5077(19)
_cell_length_c                   19.805(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.06(3)
_cell_angle_gamma                90.00
_cell_volume                     1074.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3533
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      27.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10301
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2464
_reflns_number_gt                1273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.0754P)²+0.3164P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     163
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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
O1 O -0.6478(5) 0.1839(4) -0.04298(15) 0.1053(11) Uani 1 1 d . . .
O2 O -0.4741(4) 0.3050(3) 0.03651(13) 0.0763(8) Uani 1 1 d . . .
O3 O -0.2706(4) 0.1750(3) -0.02364(12) 0.0746(7) Uani 1 1 d . . .
O4 O 0.3435(4) -0.3815(2) 0.16841(13) 0.0737(7) Uani 1 1 d . . .
O5 O 0.6643(4) -0.3062(3) 0.21825(14) 0.0806(8) Uani 1 1 d . . .
O6 O 0.6164(4) -0.5278(3) 0.19767(14) 0.0854(8) Uani 1 1 d . . .
N1 N 0.2649(5) -0.0995(3) 0.17353(13) 0.0528(7) Uani 1 1 d D . .
H1N1 H 0.308(6) -0.1864(15) 0.1742(18) 0.079 Uiso 1 1 d D . .
N2 N 0.0544(4) 0.3439(2) 0.05674(12) 0.0433(6) Uani 1 1 d D . .
H2N1 H 0.193(2) 0.324(3) 0.0444(14) 0.065 Uiso 1 1 d D . .
H2N2 H -0.044(3) 0.291(3) 0.0326(13) 0.065 Uiso 1 1 d D . .
N3 N -0.4663(5) 0.2200(3) -0.01073(14) 0.0610(8) Uani 1 1 d . . .
N4 N 0.5462(5) -0.4052(3) 0.19364(13) 0.0539(7) Uani 1 1 d . . .
C1 C 0.0540(5) -0.0771(3) 0.14232(16) 0.0529(8) Uani 1 1 d . . .
H1 H -0.0442 -0.1526 0.1302 0.064 Uiso 1 1 calc R . .
C2 C -0.0182(5) 0.0565(3) 0.12819(15) 0.0494(7) Uani 1 1 d . . .
H2 H -0.1661 0.0728 0.1063 0.059 Uiso 1 1 calc R . .
C3 C 0.1286(5) 0.1684(3) 0.14642(13) 0.0428(7) Uani 1 1 d . . .
C4 C 0.3455(5) 0.1404(3) 0.17967(15) 0.0503(7) Uani 1 1 d . . .
H4 H 0.4468 0.2136 0.1931 0.060 Uiso 1 1 calc R . .
C5 C 0.4098(5) 0.0041(3) 0.19259(16) 0.0562(8) Uani 1 1 d . . .
H5 H 0.5558 -0.0159 0.2148 0.067 Uiso 1 1 calc R . .
C6 C 0.0540(5) 0.3169(3) 0.13057(14) 0.0493(7) Uani 1 1 d . . .
H6A H -0.1020 0.3324 0.1445 0.059 Uiso 1 1 calc R . .
H6B H 0.1605 0.3816 0.1555 0.059 Uiso 1 1 calc R . .
C7 C -0.0005(5) 0.4919(3) 0.03774(14) 0.0485(7) Uani 1 1 d . . .
H7A H 0.1152 0.5541 0.0606 0.058 Uiso 1 1 calc R . .
H7B H -0.1533 0.5172 0.0516 0.058 Uiso 1 1 calc R . .

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
O1 0.0606(17) 0.142(3) 0.107(2) -0.035(2) -0.0250(15) -0.0141(17)
O2 0.0454(13) 0.097(2) 0.0865(18) -0.0331(16) 0.0048(12) -0.0040(12)
O3 0.0559(14) 0.0970(19) 0.0708(16) -0.0160(14) 0.0045(12) 0.0125(13)
O4 0.0619(15) 0.0540(15) 0.0988(19) -0.0027(13) -0.0288(13) 0.0046(11)
O5 0.0733(16) 0.0583(15) 0.1037(19) 0.0038(14) -0.0281(14) -0.0131(13)
O6 0.0782(17) 0.0555(16) 0.118(2) -0.0107(15) -0.0158(15) 0.0205(13)
N1 0.0630(17) 0.0401(15) 0.0546(15) 0.0021(12) 0.0010(13) 0.0078(13)
N2 0.0398(13) 0.0421(14) 0.0468(14) 0.0025(11) -0.0034(10) 0.0051(10)
N3 0.0456(16) 0.076(2) 0.0600(18) 0.0011(15) -0.0043(14) -0.0044(14)
N4 0.0561(16) 0.0443(16) 0.0597(17) 0.0035(12) -0.0044(13) 0.0037(13)
C1 0.0540(18) 0.0471(18) 0.0559(19) -0.0001(14) -0.0054(15) -0.0062(14)
C2 0.0415(16) 0.0485(18) 0.0567(19) 0.0020(14) -0.0047(14) -0.0006(13)
C3 0.0472(16) 0.0440(16) 0.0374(14) 0.0009(12) 0.0040(12) 0.0060(13)
C4 0.0445(16) 0.0537(19) 0.0504(17) 0.0012(14) -0.0080(13) -0.0033(14)
C5 0.0483(17) 0.061(2) 0.0570(19) 0.0073(16) -0.0061(14) 0.0112(16)
C6 0.0591(18) 0.0453(17) 0.0427(17) 0.0030(13) -0.0011(14) 0.0062(14)
C7 0.0506(16) 0.0408(16) 0.0526(16) 0.0040(14) -0.0046(14) 0.0048(12)

_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
O1 N3 1.220(3) . ?
O2 N3 1.241(3) . ?
O3 N3 1.247(3) . ?
O4 N4 1.243(3) . ?
O5 N4 1.234(3) . ?
O6 N4 1.233(3) . ?
N1 C5 1.321(4) . ?
N1 C1 1.325(4) . ?
N1 H1N1 0.86(3) . ?
N2 C7 1.483(3) . ?
N2 C6 1.485(4) . ?
N2 H2N1 0.87(3) . ?
N2 H2N2 0.87(3) . ?
C1 C2 1.357(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 C6 1.500(4) . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.503(6) 3_565 ?
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
C5 N1 C1 122.5(3) . . ?
C5 N1 H1N1 123(3) . . ?
C1 N1 H1N1 114(3) . . ?
C7 N2 C6 113.3(2) . . ?
C7 N2 H2N1 108(2) . . ?
C6 N2 H2N1 109(2) . . ?
C7 N2 H2N2 107(2) . . ?
C6 N2 H2N2 113(2) . . ?
H2N1 N2 H2N2 106.4(15) . . ?
O1 N3 O2 119.5(3) . . ?
O1 N3 O3 122.4(3) . . ?
O2 N3 O3 118.1(3) . . ?
O6 N4 O5 122.1(3) . . ?
O6 N4 O4 119.0(3) . . ?
O5 N4 O4 118.7(3) . . ?
N1 C1 C2 119.7(3) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 C6 120.6(3) . . ?
C2 C3 C6 120.9(3) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 120.1(3) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N2 C6 C3 110.1(2) . . ?
N2 C6 H6A 109.6 . . ?
C3 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C3 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C7 109.3(3) . 3_565 ?
N2 C7 H7A 109.8 . . ?
C7 C7 H7A 109.8 3_565 . ?
N2 C7 H7B 109.8 . . ?
C7 C7 H7B 109.8 3_565 . ?
H7A C7 H7B 108.3 . . ?

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
C5 N1 C1 C2 0.8(5) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C3 C6 179.2(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C6 C3 C4 C5 -179.1(3) . . . . ?
C1 N1 C5 C4 -0.7(5) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?
C7 N2 C6 C3 -175.7(2) . . . . ?
C4 C3 C6 N2 107.9(3) . . . . ?
C2 C3 C6 N2 -72.1(3) . . . . ?
C6 N2 C7 C7 -179.2(3) . . . 3_565 ?

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
N1 H1N1 O4 0.86(3) 1.870(13) 2.722(3) 169(4) .
N1 H1N1 O5 0.86(3) 2.43(3) 3.086(4) 133(3) .
N2 H2N1 O2 0.87(3) 1.936(11) 2.789(3) 166(2) 1_655
N2 H2N1 O1 0.87(3) 2.43(2) 3.118(4) 137(2) 1_655
N2 H2N2 O3 0.87(3) 1.973(10) 2.838(4) 178(3) .
N2 H2N2 O2 0.87(3) 2.48(2) 3.041(3) 123(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 996138'
#######################################################################
#
#                 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_complex13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(N O3)'
_chemical_formula_sum            'C14 H22 N8 O12'
_chemical_formula_weight         494.40

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'

_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                   6.6103(13)
_cell_length_b                   8.2099(16)
_cell_length_c                   10.764(2)
_cell_angle_alpha                90.07(3)
_cell_angle_beta                 100.10(3)
_cell_angle_gamma                111.18(3)
_cell_volume                     534.94(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3891
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             258
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4226
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1873
_reflns_number_gt                1497
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.0726P)²+0.1122P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1873
_refine_ls_number_parameters     164
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.089
_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
O1 O 0.7601(5) 0.4965(3) 1.29494(17) 0.1007(8) Uani 1 1 d . . .
O2 O 0.7480(4) 0.5489(2) 1.48361(15) 0.0783(6) Uani 1 1 d . . .
O3 O 0.6382(4) 0.2830(2) 1.4093(2) 0.1098(8) Uani 1 1 d . . .
O4 O 0.9889(3) 1.11510(17) 1.19826(14) 0.0566(4) Uani 1 1 d . . .
O5 O 1.0319(3) 0.86766(18) 1.19816(14) 0.0585(4) Uani 1 1 d . . .
O6 O 1.2243(3) 1.0771(2) 1.09708(16) 0.0671(5) Uani 1 1 d . . .
N1 N 0.2094(3) 0.4446(2) 1.13303(17) 0.0474(5) Uani 1 1 d D . .
H1N H 0.129(4) 0.3429(19) 1.153(2) 0.071 Uiso 1 1 d D . .
N2 N 0.7596(3) 0.86142(19) 1.37775(14) 0.0371(4) Uani 1 1 d D . .
H2N1 H 0.832(3) 0.875(2) 1.3166(15) 0.056 Uiso 1 1 d D . .
H2N2 H 0.745(4) 0.7597(17) 1.4052(18) 0.056 Uiso 1 1 d D . .
N3 N 0.7156(3) 0.4401(2) 1.39470(18) 0.0574(5) Uani 1 1 d . . .
N4 N 1.0857(3) 1.0205(2) 1.16330(15) 0.0454(4) Uani 1 1 d . . .
C1 C 0.3003(3) 0.5618(2) 1.23131(18) 0.0424(5) Uani 1 1 d . . .
H1 H 0.2780 0.5290 1.3120 0.051 Uiso 1 1 calc R . .
C2 C 0.4272(3) 0.7314(2) 1.21424(16) 0.0365(4) Uani 1 1 d . . .
C3 C 0.4535(3) 0.7755(2) 1.09247(17) 0.0402(5) Uani 1 1 d . . .
H3 H 0.5392 0.8894 1.0784 0.048 Uiso 1 1 calc R . .
C4 C 0.3535(3) 0.6518(3) 0.99169(17) 0.0449(5) Uani 1 1 d . . .
H4 H 0.3682 0.6819 0.9096 0.054 Uiso 1 1 calc R . .
C5 C 0.2329(3) 0.4845(3) 1.01458(19) 0.0462(5) Uani 1 1 d . . .
H5 H 0.1674 0.3986 0.9482 0.055 Uiso 1 1 calc R . .
C6 C 0.5356(3) 0.8623(3) 1.32544(18) 0.0445(5) Uani 1 1 d . . .
H6A H 0.5482 0.9782 1.2996 0.053 Uiso 1 1 calc R . .
H6B H 0.4456 0.8340 1.3903 0.053 Uiso 1 1 calc R . .
C7 C 0.8838(3) 0.9982(2) 1.48095(17) 0.0421(5) Uani 1 1 d . . .
H7A H 0.8104 0.9744 1.5531 0.051 Uiso 1 1 calc R . .
H7B H 0.8878 1.1114 1.4530 0.051 Uiso 1 1 calc R . .

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
O1 0.170(2) 0.0956(15) 0.0478(10) 0.0092(10) 0.0264(12) 0.0591(15)
O2 0.1322(17) 0.0636(10) 0.0505(9) 0.0095(8) 0.0269(10) 0.0451(11)
O3 0.138(2) 0.0440(10) 0.152(2) 0.0171(12) 0.0366(17) 0.0350(11)
O4 0.0653(10) 0.0400(7) 0.0706(10) 0.0050(7) 0.0324(8) 0.0176(7)
O5 0.0752(10) 0.0425(8) 0.0654(10) 0.0127(7) 0.0290(8) 0.0235(7)
O6 0.0665(10) 0.0652(10) 0.0755(11) 0.0144(8) 0.0428(9) 0.0175(8)
N1 0.0405(9) 0.0349(8) 0.0612(11) 0.0044(8) 0.0056(8) 0.0091(7)
N2 0.0421(9) 0.0343(8) 0.0338(8) -0.0025(6) 0.0075(7) 0.0126(7)
N3 0.0731(13) 0.0471(10) 0.0564(11) 0.0055(9) 0.0094(9) 0.0287(9)
N4 0.0472(9) 0.0415(9) 0.0441(9) 0.0026(7) 0.0138(8) 0.0099(8)
C1 0.0410(10) 0.0430(10) 0.0408(10) 0.0071(8) 0.0057(8) 0.0134(8)
C2 0.0341(9) 0.0375(9) 0.0392(10) 0.0000(7) 0.0074(7) 0.0147(8)
C3 0.0366(9) 0.0373(9) 0.0458(11) 0.0042(8) 0.0098(8) 0.0117(8)
C4 0.0418(10) 0.0579(12) 0.0369(10) 0.0024(9) 0.0087(8) 0.0200(10)
C5 0.0381(10) 0.0480(11) 0.0499(11) -0.0121(9) -0.0011(8) 0.0172(9)
C6 0.0420(10) 0.0489(11) 0.0448(10) -0.0062(9) 0.0045(8) 0.0207(9)
C7 0.0488(11) 0.0401(10) 0.0385(10) -0.0066(8) 0.0030(8) 0.0201(9)

_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
O1 N3 1.211(3) . ?
O2 N3 1.244(2) . ?
O3 N3 1.225(3) . ?
O4 N4 1.264(2) . ?
O5 N4 1.252(2) . ?
O6 N4 1.219(2) . ?
N1 C1 1.328(3) . ?
N1 C5 1.338(3) . ?
N1 H1N 0.86(3) . ?
N2 C7 1.476(2) . ?
N2 C6 1.492(2) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(2) . ?
C2 C6 1.497(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.508(4) 2_778 ?
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
C1 N1 C5 122.68(16) . . ?
C1 N1 H1N 113.5(18) . . ?
C5 N1 H1N 123.7(18) . . ?
C7 N2 C6 113.09(14) . . ?
C7 N2 H2N1 110.1(15) . . ?
C6 N2 H2N1 108.3(15) . . ?
C7 N2 H2N2 109.5(14) . . ?
C6 N2 H2N2 108.5(15) . . ?
H2N1 N2 H2N2 107.1(13) . . ?
O1 N3 O3 122.6(2) . . ?
O1 N3 O2 117.28(19) . . ?
O3 N3 O2 120.1(2) . . ?
O6 N4 O5 121.99(17) . . ?
O6 N4 O4 120.52(16) . . ?
O5 N4 O4 117.48(16) . . ?
N1 C1 C2 120.21(17) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 118.07(17) . . ?
C1 C2 C6 120.27(17) . . ?
C3 C2 C6 121.66(16) . . ?
C4 C3 C2 120.48(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 118.89(18) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 119.65(18) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C2 110.22(14) . . ?
N2 C6 H6A 109.6 . . ?
C2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C2 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C7 109.93(18) . 2_778 ?
N2 C7 H7A 109.7 . . ?
C7 C7 H7A 109.7 2_778 . ?
N2 C7 H7B 109.7 . . ?
C7 C7 H7B 109.7 2_778 . ?
H7A C7 H7B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.0(3) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
N1 C1 C2 C6 -178.07(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C6 C2 C3 C4 179.31(16) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C3 C4 C5 N1 1.6(3) . . . . ?
C7 N2 C6 C2 175.06(15) . . . . ?
C1 C2 C6 N2 89.7(2) . . . . ?
C3 C2 C6 N2 -89.3(2) . . . . ?
C6 N2 C7 C7 -173.88(19) . . . 2_778 ?

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
N1 H1N O4 0.86(3) 1.873(11) 2.730(2) 172(3) 1_445
N2 H2N1 O5 0.86(3) 2.003(11) 2.852(2) 166.2(18) .
N2 H2N1 O4 0.86(3) 2.361(14) 3.020(2) 133.2(16) .
N2 H2N2 O2 0.86(3) 1.931(10) 2.790(2) 172(2) .
N2 H2N2 O1 0.86(3) 2.505(17) 3.126(3) 129.4(15) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 996139'
#######################################################################
#
#                 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_complex14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(N O3)'
_chemical_formula_sum            'C14 H22 N8 O12'
_chemical_formula_weight         494.40

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'
O O 0.0106 0.0060 '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           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                   6.9394(10)
_cell_length_b                   7.4069(9)
_cell_length_c                   11.1290(12)
_cell_angle_alpha                96.147(10)
_cell_angle_beta                 105.845(11)
_cell_angle_gamma                109.686(13)
_cell_volume                     505.46(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1448
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             258
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2967
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         27.55
_reflns_number_total             2295
_reflns_number_gt                1943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.0449P)²+0.0799P] 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       0.58(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     164
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O1 O 0.23351(17) 0.85884(15) 0.72672(11) 0.0414(3) Uani 1 1 d . . .
O2 O 0.54585(18) 0.94059(16) 0.87293(10) 0.0439(3) Uani 1 1 d . . .
O3 O 0.49332(19) 1.13530(16) 0.74807(12) 0.0520(3) Uani 1 1 d . . .
O4 O -0.54267(16) 0.18425(15) 0.41793(10) 0.0381(3) Uani 1 1 d . . .
O5 O -0.4179(2) 0.46294(17) 0.36742(15) 0.0633(4) Uani 1 1 d . . .
O6 O -0.76276(19) 0.29368(18) 0.30232(12) 0.0481(3) Uani 1 1 d . . .
N1 N 0.15472(18) 0.54435(16) 0.83942(11) 0.0269(3) Uani 1 1 d D . .
H1N H 0.170(3) 0.6404(19) 0.7994(15) 0.040 Uiso 1 1 d D . .
N2 N -0.15126(17) 0.14307(15) 0.55354(10) 0.0234(3) Uani 1 1 d D . .
H2N1 H -0.229(2) 0.0451(18) 0.5793(13) 0.035 Uiso 1 1 d D . .
H2N2 H -0.233(2) 0.142(2) 0.4798(10) 0.035 Uiso 1 1 d D . .
N3 N 0.4281(2) 0.98033(17) 0.78418(11) 0.0313(3) Uani 1 1 d . . .
N4 N -0.5738(2) 0.31704(16) 0.36200(11) 0.0314(3) Uani 1 1 d . . .
C1 C 0.0319(2) 0.35817(18) 0.77396(12) 0.0236(3) Uani 1 1 d . . .
C2 C 0.0244(2) 0.2087(2) 0.83876(14) 0.0324(3) Uani 1 1 d . . .
H2A H -0.0573 0.0784 0.7959 0.039 Uiso 1 1 calc R . .
C3 C 0.1398(2) 0.2547(2) 0.96842(14) 0.0379(4) Uani 1 1 d . . .
H3A H 0.1381 0.1543 1.0122 0.045 Uiso 1 1 calc R . .
C4 C 0.2573(2) 0.4482(2) 1.03348(14) 0.0359(3) Uani 1 1 d . . .
H4A H 0.3308 0.4799 1.1211 0.043 Uiso 1 1 calc R . .
C5 C 0.2624(2) 0.5917(2) 0.96504(13) 0.0335(3) Uani 1 1 d . . .
H5A H 0.3414 0.7230 1.0063 0.040 Uiso 1 1 calc R . .
C6 C -0.0933(2) 0.33758(18) 0.63670(13) 0.0275(3) Uani 1 1 d . . .
H6A H -0.2254 0.3584 0.6328 0.033 Uiso 1 1 calc R . .
H6B H -0.0079 0.4395 0.6031 0.033 Uiso 1 1 calc R . .
C7 C 0.0384(2) 0.10587(18) 0.53576(13) 0.0262(3) Uani 1 1 d . . .
H7A H 0.1462 0.1284 0.6184 0.031 Uiso 1 1 calc R . .
H7B H 0.1042 0.1949 0.4874 0.031 Uiso 1 1 calc R . .

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
O1 0.0312(6) 0.0358(6) 0.0449(6) 0.0147(5) 0.0016(5) 0.0049(4)
O2 0.0417(6) 0.0461(7) 0.0333(6) 0.0135(5) -0.0009(5) 0.0132(5)
O3 0.0474(7) 0.0323(6) 0.0602(8) 0.0209(5) 0.0039(6) 0.0035(5)
O4 0.0326(6) 0.0403(6) 0.0429(6) 0.0197(5) 0.0117(5) 0.0133(5)
O5 0.0630(9) 0.0332(6) 0.0796(10) 0.0113(6) 0.0330(8) -0.0059(6)
O6 0.0448(7) 0.0585(8) 0.0489(7) 0.0194(6) 0.0125(6) 0.0294(6)
N1 0.0313(6) 0.0214(5) 0.0256(6) 0.0055(4) 0.0095(5) 0.0067(5)
N2 0.0226(5) 0.0227(5) 0.0213(5) 0.0042(4) 0.0037(4) 0.0072(4)
N3 0.0332(6) 0.0267(6) 0.0295(6) 0.0053(5) 0.0058(5) 0.0100(5)
N4 0.0365(7) 0.0257(6) 0.0315(6) 0.0063(5) 0.0152(5) 0.0084(5)
C1 0.0234(6) 0.0238(6) 0.0242(6) 0.0050(5) 0.0099(5) 0.0084(5)
C2 0.0346(8) 0.0242(6) 0.0310(7) 0.0073(5) 0.0059(6) 0.0058(6)
C3 0.0397(8) 0.0369(8) 0.0338(8) 0.0183(6) 0.0095(7) 0.0097(6)
C4 0.0332(8) 0.0433(8) 0.0240(7) 0.0081(6) 0.0060(6) 0.0084(6)
C5 0.0345(8) 0.0292(7) 0.0267(7) -0.0003(5) 0.0071(6) 0.0042(6)
C6 0.0328(7) 0.0229(6) 0.0255(7) 0.0046(5) 0.0061(6) 0.0119(5)
C7 0.0234(6) 0.0246(7) 0.0280(7) 0.0030(5) 0.0083(5) 0.0073(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
O1 N3 1.2764(16) . ?
O2 N3 1.2301(16) . ?
O3 N3 1.2377(15) . ?
O4 N4 1.2659(15) . ?
O5 N4 1.2265(16) . ?
O6 N4 1.2399(16) . ?
N1 C5 1.3356(18) . ?
N1 C1 1.3465(17) . ?
N1 H1N 0.87(9) . ?
N2 C6 1.4881(16) . ?
N2 C7 1.4908(16) . ?
N2 H2N1 0.87(8) . ?
N2 H2N2 0.86(8) . ?
C1 C2 1.3789(18) . ?
C1 C6 1.4991(18) . ?
C2 C3 1.385(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(2) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.522(2) 2_556 ?
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
C5 N1 C1 123.14(12) . . ?
C5 N1 H1N 116.8(12) . . ?
C1 N1 H1N 120.0(11) . . ?
C6 N2 C7 114.07(10) . . ?
C6 N2 H2N1 112.8(10) . . ?
C7 N2 H2N1 109.4(10) . . ?
C6 N2 H2N2 106.3(10) . . ?
C7 N2 H2N2 107.9(10) . . ?
H2N1 N2 H2N2 105.9(11) . . ?
O2 N3 O3 121.82(13) . . ?
O2 N3 O1 119.55(12) . . ?
O3 N3 O1 118.63(12) . . ?
O5 N4 O6 122.15(13) . . ?
O5 N4 O4 119.52(13) . . ?
O6 N4 O4 118.33(11) . . ?
N1 C1 C2 118.34(12) . . ?
N1 C1 C6 114.92(11) . . ?
C2 C1 C6 126.66(12) . . ?
C1 C2 C3 119.26(13) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 120.73(13) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C3 118.00(14) . . ?
C5 C4 H4A 121.0 . . ?
C3 C4 H4A 121.0 . . ?
N1 C5 C4 120.44(13) . . ?
N1 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
N2 C6 C1 113.87(10) . . ?
N2 C6 H6A 108.8 . . ?
C1 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C7 108.89(13) . 2_556 ?
N2 C7 H7A 109.9 . . ?
C7 C7 H7A 109.9 2_556 . ?
N2 C7 H7B 109.9 . . ?
C7 C7 H7B 109.9 2_556 . ?
H7A C7 H7B 108.3 . . ?

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
C5 N1 C1 C2 -2.80(19) . . . . ?
C5 N1 C1 C6 174.16(12) . . . . ?
N1 C1 C2 C3 1.0(2) . . . . ?
C6 C1 C2 C3 -175.60(13) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C1 N1 C5 C4 2.0(2) . . . . ?
C3 C4 C5 N1 0.6(2) . . . . ?
C7 N2 C6 C1 -67.07(14) . . . . ?
N1 C1 C6 N2 155.94(11) . . . . ?
C2 C1 C6 N2 -27.39(19) . . . . ?
C6 N2 C7 C7 172.66(13) . . . 2_556 ?

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
N2 H2N1 O4 0.87(8) 1.903(10) 2.7484(15) 162.0(13) 2_456
N2 H2N2 O4 0.86(8) 2.207(13) 2.8577(15) 132.3(13) .
N2 H2N2 O1 0.86(8) 2.296(11) 3.0112(16) 140.7(13) 2_566

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 996140'
#######################################################################
#
#                 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_complex15

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(Cl O4)'
_chemical_formula_sum            'C14 H22 Cl4 N4 O16'
_chemical_formula_weight         644.16

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   5.7513(12)
_cell_length_b                   11.129(2)
_cell_length_c                   18.787(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.86(3)
_cell_angle_gamma                90.00
_cell_volume                     1196.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7904
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      27.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8874
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19113
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2751
_reflns_number_gt                1601
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.1005P)²+2.1018P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     182
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2253
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_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 0.1262(2) 0.52543(11) -0.34598(7) 0.0503(4) Uani 1 1 d . . .
Cl2 Cl -0.1376(2) 0.63051(11) 0.09352(7) 0.0516(4) Uani 1 1 d . . .
O1 O 0.1185(7) 0.4220(3) -0.3911(3) 0.0709(12) Uani 1 1 d . . .
O2 O -0.1013(6) 0.5752(4) -0.3471(3) 0.0734(12) Uani 1 1 d . . .
O3 O 0.2889(7) 0.6104(4) -0.3677(2) 0.0652(11) Uani 1 1 d . . .
O4 O 0.2010(11) 0.4922(6) -0.2738(2) 0.1108(19) Uani 1 1 d . . .
O5 O 0.0491(8) 0.6348(5) 0.1493(3) 0.0976(18) Uani 1 1 d . . .
O6 O -0.1733(9) 0.5116(4) 0.0701(3) 0.1035(18) Uani 1 1 d . . .
O7 O -0.0835(7) 0.7067(4) 0.0355(2) 0.0702(12) Uani 1 1 d . . .
O8 O -0.3456(7) 0.6761(4) 0.1193(2) 0.0705(12) Uani 1 1 d . . .
N1 N -0.3536(7) 0.7009(4) -0.2414(2) 0.0486(10) Uani 1 1 d D . .
H1N1 H -0.311(10) 0.693(6) -0.2836(14) 0.073 Uiso 1 1 d D . .
N2 N -0.5149(8) 0.8316(4) 0.0007(2) 0.0480(10) Uani 1 1 d D . .
H2N1 H -0.555(8) 0.828(5) 0.0436(12) 0.072 Uiso 1 1 d D . .
H2N2 H -0.365(2) 0.826(6) 0.004(3) 0.072 Uiso 1 1 d D . .
C1 C -0.5357(9) 0.7721(5) -0.2377(3) 0.0505(12) Uani 1 1 d . . .
H1 H -0.5974 0.8151 -0.2778 0.061 Uiso 1 1 calc R . .
C2 C -0.6334(8) 0.7821(5) -0.1739(3) 0.0476(11) Uani 1 1 d . . .
H2 H -0.7645 0.8300 -0.1710 0.057 Uiso 1 1 calc R . .
C3 C -0.5367(8) 0.7213(4) -0.1151(2) 0.0411(10) Uani 1 1 d . . .
C4 C -0.3484(9) 0.6458(5) -0.1222(3) 0.0495(12) Uani 1 1 d . . .
H4 H -0.2838 0.6006 -0.0834 0.059 Uiso 1 1 calc R . .
C5 C -0.2593(9) 0.6383(5) -0.1865(3) 0.0497(12) Uani 1 1 d . . .
H5 H -0.1316 0.5889 -0.1916 0.060 Uiso 1 1 calc R . .
C6 C -0.6352(9) 0.7343(5) -0.0445(3) 0.0507(12) Uani 1 1 d . . .
H6A H -0.8006 0.7526 -0.0529 0.061 Uiso 1 1 calc R . .
H6B H -0.6187 0.6587 -0.0188 0.061 Uiso 1 1 calc R . .
C7 C -0.5733(8) 0.9562(4) -0.0225(2) 0.0427(11) Uani 1 1 d . . .
H7A H -0.7373 0.9717 -0.0184 0.051 Uiso 1 1 calc R . .
H7B H -0.5461 0.9660 -0.0723 0.051 Uiso 1 1 calc R . .

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 0.0494(7) 0.0435(7) 0.0601(8) 0.0018(5) 0.0164(6) 0.0017(5)
Cl2 0.0532(7) 0.0445(7) 0.0579(8) -0.0058(5) 0.0088(6) -0.0008(5)
O1 0.060(2) 0.045(2) 0.112(3) -0.026(2) 0.028(2) -0.0035(18)
O2 0.049(2) 0.070(3) 0.104(3) -0.025(2) 0.021(2) 0.0061(19)
O3 0.070(3) 0.057(2) 0.072(3) -0.0084(19) 0.027(2) -0.0212(19)
O4 0.145(5) 0.125(5) 0.062(3) 0.038(3) 0.007(3) 0.016(4)
O5 0.080(3) 0.099(4) 0.104(4) 0.033(3) -0.041(3) -0.020(3)
O6 0.113(4) 0.047(3) 0.154(5) -0.036(3) 0.034(3) -0.018(3)
O7 0.068(2) 0.096(3) 0.050(2) 0.008(2) 0.0247(18) -0.005(2)
O8 0.077(3) 0.080(3) 0.060(2) 0.012(2) 0.034(2) 0.020(2)
N1 0.050(2) 0.056(3) 0.040(2) -0.0062(19) 0.0041(18) 0.0045(19)
N2 0.064(3) 0.041(2) 0.039(2) -0.0011(17) 0.0083(19) 0.002(2)
C1 0.056(3) 0.056(3) 0.039(2) -0.002(2) 0.000(2) 0.005(2)
C2 0.044(3) 0.052(3) 0.047(3) -0.009(2) 0.005(2) 0.004(2)
C3 0.048(2) 0.037(2) 0.039(2) -0.0072(19) 0.0100(19) -0.007(2)
C4 0.061(3) 0.047(3) 0.041(3) -0.001(2) 0.008(2) 0.011(2)
C5 0.052(3) 0.052(3) 0.046(3) -0.004(2) 0.008(2) 0.012(2)
C6 0.062(3) 0.045(3) 0.048(3) -0.010(2) 0.022(2) -0.009(2)
C7 0.050(3) 0.040(3) 0.038(2) -0.0005(19) 0.003(2) 0.003(2)

_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 O2 1.419(4) . ?
Cl1 O3 1.419(4) . ?
Cl1 O1 1.428(4) . ?
Cl1 O4 1.428(5) . ?
Cl2 O6 1.403(4) . ?
Cl2 O5 1.423(4) . ?
Cl2 O8 1.429(4) . ?
Cl2 O7 1.439(4) . ?
N1 C5 1.315(6) . ?
N1 C1 1.321(6) . ?
N1 H1N1 0.86(4) . ?
N2 C7 1.482(6) . ?
N2 C6 1.500(6) . ?
N2 H2N1 0.86(4) . ?
N2 H2N2 0.86(4) . ?
C1 C2 1.380(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(7) . ?
C3 C6 1.502(6) . ?
C4 C5 1.362(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.494(9) 3_475 ?
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
O2 Cl1 O3 111.7(3) . . ?
O2 Cl1 O1 109.4(2) . . ?
O3 Cl1 O1 110.3(2) . . ?
O2 Cl1 O4 107.7(3) . . ?
O3 Cl1 O4 107.6(3) . . ?
O1 Cl1 O4 110.1(3) . . ?
O6 Cl2 O5 109.8(4) . . ?
O6 Cl2 O8 109.9(3) . . ?
O5 Cl2 O8 109.5(3) . . ?
O6 Cl2 O7 110.7(3) . . ?
O5 Cl2 O7 109.4(3) . . ?
O8 Cl2 O7 107.5(2) . . ?
C5 N1 C1 122.9(4) . . ?
C5 N1 H1N1 122(4) . . ?
C1 N1 H1N1 114(4) . . ?
C7 N2 C6 115.6(4) . . ?
C7 N2 H2N1 104(4) . . ?
C6 N2 H2N1 110(4) . . ?
C7 N2 H2N2 107(4) . . ?
C6 N2 H2N2 113(4) . . ?
H2N1 N2 H2N2 107.2(17) . . ?
N1 C1 C2 119.2(5) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 C6 120.5(4) . . ?
C4 C3 C6 120.8(5) . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 120.1(5) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N2 C6 C3 112.1(4) . . ?
N2 C6 H6A 109.2 . . ?
C3 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C3 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C7 110.3(5) . 3_475 ?
N2 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 3_475 . ?
N2 C7 H7B 109.6 . . ?
C7 C7 H7B 109.6 3_475 . ?
H7A C7 H7B 108.1 . . ?

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
C5 N1 C1 C2 -0.1(8) . . . . ?
N1 C1 C2 C3 1.9(8) . . . . ?
C1 C2 C3 C4 -3.3(7) . . . . ?
C1 C2 C3 C6 177.8(4) . . . . ?
C2 C3 C4 C5 2.8(7) . . . . ?
C6 C3 C4 C5 -178.3(5) . . . . ?
C1 N1 C5 C4 -0.4(8) . . . . ?
C3 C4 C5 N1 -1.0(8) . . . . ?
C7 N2 C6 C3 73.5(5) . . . . ?
C2 C3 C6 N2 -92.6(6) . . . . ?
C4 C3 C6 N2 88.6(6) . . . . ?
C6 N2 C7 C7 -174.9(5) . . . 3_475 ?

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
N1 H1N1 O2 0.86(4) 2.21(4) 2.933(6) 142(5) .
N1 H1N1 O8 0.86(4) 2.33(5) 2.958(6) 130(5) 4_575
N2 H2N1 O3 0.86(4) 2.09(3) 2.893(6) 155(5) 4_476
N2 H2N2 O7 0.86(4) 2.13(4) 2.861(6) 143(5) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 996141'
#######################################################################
#
#                 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_complex16

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(Cl O4)'
_chemical_formula_sum            'C14 H22 Cl4 N4 O16'
_chemical_formula_weight         644.16

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'
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/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                   13.246(3)
_cell_length_b                   7.0335(14)
_cell_length_c                   13.834(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.68(3)
_cell_angle_gamma                90.00
_cell_volume                     1180.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3766
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      24.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8860
_exptl_absorpt_correction_T_max  0.9272
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8435
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2081
_reflns_number_gt                1694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group.
;

_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)+(0.0565P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2081
_refine_ls_number_parameters     181
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.005
_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 0.34183(13) 1.74274(14) 0.18075(9) 0.0692(5) Uani 1 1 d . . .
Cl2 Cl 0.74626(14) 0.58453(16) 0.36481(10) 0.0770(5) Uani 1 1 d . . .
O1 O 0.4462(3) 1.7498(4) 0.1711(3) 0.0858(11) Uani 1 1 d . . .
O2 O 0.2839(3) 1.5774(4) 0.1250(2) 0.0851(11) Uani 1 1 d . . .
O3 O 0.2809(3) 1.9089(4) 0.1377(3) 0.0905(12) Uani 1 1 d . . .
O4 O 0.3605(4) 1.7261(5) 0.2882(3) 0.1113(15) Uani 1 1 d . . .
O5 O 0.7094(4) 0.5774(6) 0.2543(3) 0.1165(15) Uani 1 1 d . . .
O6 O 0.7772(4) 0.7700(5) 0.4006(3) 0.1131(15) Uani 1 1 d . . .
O7 O 0.8345(7) 0.4726(9) 0.4097(4) 0.256(5) Uani 1 1 d . . .
O8 O 0.6606(7) 0.5397(12) 0.3898(5) 0.243(4) Uani 1 1 d . . .
N1 N 0.6225(4) 1.0541(5) 0.4232(3) 0.0783(13) Uani 1 1 d D . .
H1N H 0.683(3) 0.989(8) 0.442(4) 0.117 Uiso 1 1 d D . .
N2 N 0.5099(3) 1.3836(5) 0.1253(2) 0.0579(10) Uani 1 1 d D . .
H2N1 H 0.492(3) 1.480(4) 0.153(3) 0.087 Uiso 1 1 d D . .
H2N2 H 0.5802(10) 1.371(6) 0.154(3) 0.087 Uiso 1 1 d D . .
C1 C 0.5825(5) 1.0746(6) 0.3175(4) 0.0747(15) Uani 1 1 d . . .
H1 H 0.6148 1.0086 0.2790 0.090 Uiso 1 1 calc R . .
C2 C 0.4952(4) 1.1912(6) 0.2669(3) 0.0600(13) Uani 1 1 d . . .
C3 C 0.4462(5) 1.2811(6) 0.3231(4) 0.0716(14) Uani 1 1 d . . .
H3 H 0.3835 1.3547 0.2889 0.086 Uiso 1 1 calc R . .
C4 C 0.4910(6) 1.2625(6) 0.4340(4) 0.0809(17) Uani 1 1 d . . .
H4 H 0.4594 1.3241 0.4745 0.097 Uiso 1 1 calc R . .
C5 C 0.5832(5) 1.1497(7) 0.4804(4) 0.0733(15) Uani 1 1 d . . .
H5 H 0.6176 1.1421 0.5536 0.088 Uiso 1 1 calc R . .
C6 C 0.4554(5) 1.2145(5) 0.1504(3) 0.0641(14) Uani 1 1 d . . .
H6A H 0.3761 1.2319 0.1198 0.077 Uiso 1 1 calc R . .
H6B H 0.4722 1.1009 0.1199 0.077 Uiso 1 1 calc R . .
C7 C 0.4720(4) 1.4163(5) 0.0095(3) 0.0618(13) Uani 1 1 d . . .
H7A H 0.4882 1.3053 -0.0234 0.074 Uiso 1 1 calc R . .
H7B H 0.3929 1.4363 -0.0216 0.074 Uiso 1 1 calc R . .

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 0.0936(12) 0.0516(6) 0.0686(8) -0.0048(5) 0.0390(7) -0.0038(7)
Cl2 0.0903(12) 0.0562(7) 0.0752(9) -0.0011(6) 0.0234(7) -0.0059(7)
O1 0.084(3) 0.065(2) 0.117(3) -0.0174(16) 0.051(2) -0.0098(19)
O2 0.103(3) 0.0593(18) 0.085(2) -0.0106(16) 0.030(2) -0.0197(18)
O3 0.100(3) 0.0571(18) 0.120(3) 0.0147(17) 0.050(2) 0.0162(19)
O4 0.178(5) 0.096(3) 0.073(2) -0.0043(18) 0.064(3) -0.004(3)
O5 0.136(4) 0.126(3) 0.063(2) -0.0175(19) 0.015(2) -0.001(3)
O6 0.144(4) 0.078(2) 0.110(3) -0.017(2) 0.043(3) -0.010(2)
O7 0.319(10) 0.199(6) 0.123(4) -0.043(4) -0.045(4) 0.182(7)
O8 0.227(8) 0.368(10) 0.153(5) -0.038(5) 0.096(5) -0.201(8)
N1 0.087(4) 0.062(2) 0.077(3) 0.010(2) 0.024(3) 0.003(2)
N2 0.073(3) 0.0511(19) 0.049(2) 0.0064(15) 0.0233(19) -0.001(2)
C1 0.089(5) 0.063(3) 0.065(3) 0.012(2) 0.024(3) -0.008(3)
C2 0.077(4) 0.043(2) 0.057(3) 0.009(2) 0.025(3) -0.001(2)
C3 0.089(4) 0.056(2) 0.083(3) 0.013(2) 0.049(3) 0.002(3)
C4 0.118(5) 0.054(3) 0.085(4) -0.002(2) 0.056(4) -0.007(3)
C5 0.091(5) 0.061(3) 0.065(3) -0.002(3) 0.029(3) -0.007(3)
C6 0.090(4) 0.043(2) 0.061(3) 0.0019(18) 0.031(3) -0.012(2)
C7 0.078(4) 0.052(2) 0.056(3) 0.004(2) 0.027(2) 0.000(2)

_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 O3 1.409(3) . ?
Cl1 O4 1.410(3) . ?
Cl1 O2 1.435(3) . ?
Cl1 O1 1.442(4) . ?
Cl2 O7 1.338(6) . ?
Cl2 O8 1.349(6) . ?
Cl2 O6 1.397(3) . ?
Cl2 O5 1.406(3) . ?
N1 C5 1.296(6) . ?
N1 C1 1.347(6) . ?
N1 H1N 0.86(3) . ?
N2 C7 1.491(5) . ?
N2 C6 1.502(5) . ?
N2 H2N1 0.86(3) . ?
N2 H2N2 0.86(3) . ?
C1 C2 1.360(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(6) . ?
C2 C6 1.490(5) . ?
C3 C4 1.412(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.471(7) 3_685 ?
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
O3 Cl1 O4 110.0(2) . . ?
O3 Cl1 O2 110.7(2) . . ?
O4 Cl1 O2 109.1(2) . . ?
O3 Cl1 O1 109.9(2) . . ?
O4 Cl1 O1 109.4(3) . . ?
O2 Cl1 O1 107.7(2) . . ?
O7 Cl2 O8 114.3(6) . . ?
O7 Cl2 O6 107.9(4) . . ?
O8 Cl2 O6 106.6(4) . . ?
O7 Cl2 O5 109.9(3) . . ?
O8 Cl2 O5 108.0(4) . . ?
O6 Cl2 O5 110.0(2) . . ?
C5 N1 C1 121.8(5) . . ?
C5 N1 H1N 130(4) . . ?
C1 N1 H1N 107(4) . . ?
C7 N2 C6 112.6(3) . . ?
C7 N2 H2N1 109(3) . . ?
C6 N2 H2N1 106(3) . . ?
C7 N2 H2N2 111(3) . . ?
C6 N2 H2N2 110(3) . . ?
H2N1 N2 H2N2 108.3(17) . . ?
N1 C1 C2 120.4(5) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 C6 121.8(5) . . ?
C1 C2 C6 118.8(4) . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 117.7(5) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 120.8(5) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C2 C6 N2 110.1(3) . . ?
C2 C6 H6A 109.6 . . ?
N2 C6 H6A 109.6 . . ?
C2 C6 H6B 109.6 . . ?
N2 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C7 C7 N2 109.8(4) 3_685 . ?
C7 C7 H7A 109.7 3_685 . ?
N2 C7 H7A 109.7 . . ?
C7 C7 H7B 109.7 3_685 . ?
N2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -3.1(7) . . . . ?
N1 C1 C2 C3 -2.4(7) . . . . ?
N1 C1 C2 C6 178.3(4) . . . . ?
C1 C2 C3 C4 4.2(7) . . . . ?
C6 C2 C3 C4 -176.5(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C1 N1 C5 C4 6.7(8) . . . . ?
C3 C4 C5 N1 -4.7(7) . . . . ?
C3 C2 C6 N2 87.7(5) . . . . ?
C1 C2 C6 N2 -93.0(5) . . . . ?
C7 N2 C6 C2 -179.1(4) . . . . ?
C6 N2 C7 C7 179.8(5) . . . 3_685 ?

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
N1 H1N O6 0.86(3) 2.20(3) 2.968(6) 148(5) .
N2 H2N1 O1 0.86(3) 2.037(18) 2.860(5) 160(4) .
N2 H2N2 O5 0.86(3) 2.25(3) 2.871(6) 129(3) 1_565
N2 H2N2 O6 0.86(3) 2.41(3) 3.086(6) 136(3) 2_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 996142'
#######################################################################
#
#                 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_complex17

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N4, 4(Cl O4)'
_chemical_formula_sum            'C14 H22 Cl4 N4 O16'
_chemical_formula_weight         644.16

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'
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                   7.6290(15)
_cell_length_b                   8.1477(16)
_cell_length_c                   10.747(2)
_cell_angle_alpha                86.61(3)
_cell_angle_beta                 87.69(3)
_cell_angle_gamma                65.83(3)
_cell_volume                     608.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3139
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             330
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_T_max  0.9292
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3991
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2106
_reflns_number_gt                1711
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'

_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. 
 The restraint order of DFIX was used to define the distance between two
 hydrogen atoms of N and the distance between N and H atoms. Such restraint
 was mainly employed to define an appropriate geometry for the -NH₂ group
 and pyridyl NH group. Meanwhile, EXYZ, EADP were used to refine the 
 disorder between C2 and N1 of the pyridyl ring.
;

_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)+(0.0206P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2106
_refine_ls_number_parameters     185
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.27949(16) 0.40398(14) 0.61162(10) 0.0421(4) Uani 1 1 d . . .
Cl2 Cl 0.19513(16) -0.05661(15) -0.16824(11) 0.0439(4) Uani 1 1 d . . .
O1 O 0.1030(6) 0.4446(7) 0.6723(5) 0.125(2) Uani 1 1 d . . .
O2 O 0.3341(7) 0.2621(5) 0.5290(3) 0.0918(16) Uani 1 1 d . . .
O3 O 0.4207(6) 0.3494(5) 0.7041(4) 0.0972(16) Uani 1 1 d . . .
O4 O 0.2687(5) 0.5633(4) 0.5436(4) 0.0776(12) Uani 1 1 d . . .
O5 O 0.2923(6) -0.0231(6) -0.2743(5) 0.1078(18) Uani 1 1 d . . .
O6 O 0.0140(5) 0.0853(6) -0.1521(4) 0.0958(17) Uani 1 1 d . . .
O7 O 0.1617(7) -0.2100(5) -0.1924(4) 0.0961(16) Uani 1 1 d . . .
O8 O 0.3113(5) -0.0997(5) -0.0623(3) 0.0773(13) Uani 1 1 d . . .
N1 N 0.2356(6) 0.2205(6) 0.0936(4) 0.0458(14) Uani 0.76(4) 1 d PD A 1
H1N H 0.166(8) 0.177(9) 0.058(6) 0.069 Uiso 0.76(4) 1 d PD A 1
C2 C 0.3110(6) 0.3603(6) 0.2513(4) 0.0446(15) Uani 0.76(4) 1 d P A 1
H2A H 0.3416 0.3621 0.3339 0.054 Uiso 0.76(4) 1 calc PR A 1
C2' C 0.2356(6) 0.2205(6) 0.0936(4) 0.0458(14) Uani 0.24(4) 1 d P A 2
H2'A H 0.2145 0.1238 0.0667 0.055 Uiso 0.24(4) 1 calc PR A 2
N1' N 0.3110(6) 0.3603(6) 0.2513(4) 0.0446(15) Uani 0.24(4) 1 d PD A 2
H1'N H 0.350(19) 0.37(2) 0.324(6) 0.067 Uiso 0.24(4) 1 d PD A 2
N2 N 0.1037(5) 0.1289(4) 0.3897(3) 0.0346(9) Uani 1 1 d D . .
H2N1 H 0.093(5) 0.205(4) 0.446(3) 0.052 Uiso 1 1 d D . .
H2N2 H 0.009(4) 0.186(5) 0.340(3) 0.052 Uiso 1 1 d D . .
C1 C 0.2682(5) 0.2257(5) 0.2129(4) 0.0317(10) Uani 1 1 d . . .
C3 C 0.3083(8) 0.4962(7) 0.1650(7) 0.0718(18) Uani 1 1 d . . .
H3A H 0.3313 0.5926 0.1904 0.086 Uiso 1 1 calc R A 1
C4 C 0.2721(8) 0.4866(9) 0.0439(8) 0.087(3) Uani 1 1 d . A .
H4A H 0.2756 0.5739 -0.0148 0.104 Uiso 1 1 calc R . .
C5 C 0.2320(8) 0.3535(10) 0.0090(5) 0.0688(17) Uani 1 1 d . . .
H5A H 0.2012 0.3503 -0.0734 0.083 Uiso 1 1 calc R A 1
C6 C 0.2755(5) 0.0761(5) 0.3031(4) 0.0378(11) Uani 1 1 d . A .
H6A H 0.3908 0.0379 0.3520 0.045 Uiso 1 1 calc R . .
H6B H 0.2838 -0.0256 0.2569 0.045 Uiso 1 1 calc R . .
C7 C 0.0880(6) -0.0299(5) 0.4586(4) 0.0384(11) Uani 1 1 d . . .
H7A H 0.0814 -0.1126 0.3995 0.046 Uiso 1 1 calc R . .
H7B H 0.2013 -0.0930 0.5086 0.046 Uiso 1 1 calc R . .

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 0.0438(7) 0.0324(6) 0.0424(6) -0.0007(5) -0.0022(5) -0.0076(5)
Cl2 0.0393(6) 0.0338(7) 0.0565(7) -0.0009(5) -0.0007(6) -0.0128(5)
O1 0.069(3) 0.105(4) 0.173(5) 0.048(3) 0.024(3) -0.018(3)
O2 0.171(4) 0.045(2) 0.049(2) 0.0067(18) -0.033(2) -0.031(2)
O3 0.128(4) 0.058(2) 0.092(3) -0.013(2) -0.057(3) -0.018(2)
O4 0.090(3) 0.036(2) 0.096(3) 0.0091(19) 0.008(2) -0.0170(19)
O5 0.064(3) 0.101(4) 0.138(4) 0.050(3) 0.010(3) -0.022(2)
O6 0.060(3) 0.085(3) 0.099(3) -0.015(2) -0.006(2) 0.017(2)
O7 0.145(4) 0.066(3) 0.097(3) 0.018(2) -0.073(3) -0.060(3)
O8 0.068(2) 0.074(3) 0.078(3) -0.015(2) -0.027(2) -0.014(2)
N1 0.051(3) 0.056(3) 0.038(3) -0.007(2) 0.005(2) -0.029(2)
C2 0.045(3) 0.037(3) 0.052(3) -0.019(2) 0.005(2) -0.016(2)
C2' 0.051(3) 0.056(3) 0.038(3) -0.007(2) 0.005(2) -0.029(2)
N1' 0.045(3) 0.037(3) 0.052(3) -0.019(2) 0.005(2) -0.016(2)
N2 0.040(2) 0.0261(19) 0.032(2) 0.0050(14) 0.0044(16) -0.0089(15)
C1 0.030(2) 0.025(2) 0.037(2) 0.0040(17) 0.0022(18) -0.0095(18)
C3 0.065(4) 0.037(3) 0.120(6) -0.011(3) 0.021(4) -0.028(3)
C4 0.042(3) 0.065(4) 0.132(6) 0.065(4) 0.006(4) -0.010(3)
C5 0.059(3) 0.105(5) 0.042(3) 0.041(3) -0.005(2) -0.039(3)
C6 0.031(2) 0.033(2) 0.045(3) 0.0042(19) 0.011(2) -0.0093(19)
C7 0.042(3) 0.033(2) 0.037(2) 0.0127(18) -0.0011(19) -0.014(2)

_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 O1 1.392(4) . ?
Cl1 O3 1.410(4) . ?
Cl1 O2 1.413(4) . ?
Cl1 O4 1.425(4) . ?
Cl2 O6 1.404(3) . ?
Cl2 O8 1.409(4) . ?
Cl2 O5 1.409(5) . ?
Cl2 O7 1.414(4) . ?
N1 C1 1.322(5) . ?
N1 C5 1.365(7) . ?
N1 H1N 0.86(4) . ?
C2 C1 1.355(6) . ?
C2 C3 1.396(8) . ?
C2 H2A 0.9300 . ?
C2 H1'N 0.861(11) . ?
N2 C7 1.498(6) . ?
N2 C6 1.502(5) . ?
N2 H2N1 0.86(4) . ?
N2 H2N2 0.86(4) . ?
C1 C6 1.495(6) . ?
C3 C4 1.355(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.318(10) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.500(8) 2_556 ?
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
O1 Cl1 O3 107.2(3) . . ?
O1 Cl1 O2 115.0(4) . . ?
O3 Cl1 O2 106.7(2) . . ?
O1 Cl1 O4 107.3(2) . . ?
O3 Cl1 O4 111.8(3) . . ?
O2 Cl1 O4 109.0(2) . . ?
O6 Cl2 O8 113.8(2) . . ?
O6 Cl2 O5 111.2(3) . . ?
O8 Cl2 O5 110.9(3) . . ?
O6 Cl2 O7 106.7(3) . . ?
O8 Cl2 O7 107.5(2) . . ?
O5 Cl2 O7 106.3(3) . . ?
C1 N1 C5 121.6(5) . . ?
C1 N1 H1N 131(5) . . ?
C5 N1 H1N 102(5) . . ?
C1 C2 C3 119.0(5) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H1'N 127(10) . . ?
C3 C2 H1'N 114(10) . . ?
C7 N2 C6 112.7(3) . . ?
C7 N2 H2N1 105(3) . . ?
C6 N2 H2N1 118(3) . . ?
C7 N2 H2N2 113(3) . . ?
C6 N2 H2N2 102(3) . . ?
H2N1 N2 H2N2 105.3(16) . . ?
N1 C1 C2 119.4(4) . . ?
N1 C1 C6 120.5(4) . . ?
C2 C1 C6 119.8(4) . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 N1 120.2(6) . . ?
C4 C5 H5A 119.9 . . ?
N1 C5 H5A 119.9 . . ?
C1 C6 N2 113.0(3) . . ?
C1 C6 H6A 109.0 . . ?
N2 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
N2 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C7 N2 110.5(4) 2_556 . ?
C7 C7 H7A 109.6 2_556 . ?
N2 C7 H7A 109.6 . . ?
C7 C7 H7B 109.6 2_556 . ?
N2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?

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
C5 N1 C1 C2 -4.1(7) . . . . ?
C5 N1 C1 C6 -178.7(4) . . . . ?
C3 C2 C1 N1 3.7(6) . . . . ?
C3 C2 C1 C6 178.3(4) . . . . ?
C1 C2 C3 C4 -3.1(7) . . . . ?
C2 C3 C4 C5 2.7(8) . . . . ?
C3 C4 C5 N1 -3.1(9) . . . . ?
C1 N1 C5 C4 3.8(8) . . . . ?
N1 C1 C6 N2 -108.1(5) . . . . ?
C2 C1 C6 N2 77.4(5) . . . . ?
C7 N2 C6 C1 166.5(4) . . . . ?
C6 N2 C7 C7 -178.7(4) . . . 2_556 ?

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
N1 H1N O8 0.86(4) 2.49(6) 3.025(6) 121(5) .
N2 H2N1 O2 0.86(4) 2.30(3) 2.911(6) 128(3) .
N2 H2N2 O7 0.86(4) 2.039(15) 2.849(5) 155(3) 2

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.069

_database_code_depnum_ccdc_archive 'CCDC 996143'
