# 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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_red


#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Cl N4 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H13 Cl N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         300.74
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

_cell_length_a                   7.5528(3)
_cell_length_b                   12.8145(4)
_cell_length_c                   28.2258(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2731.84(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    112(4)
_cell_measurement_reflns_used    6151
_cell_measurement_theta_min      2.8690
_cell_measurement_theta_max      28.6000
_cell_special_details            
;
 
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.020
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.284
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.994

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      112(4)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_detector_area_resol_mean 16.0839

# number of measured reflections (redundant set)
_diffrn_reflns_number            21053
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2686
# number of observed reflections (> n sig(I))
_reflns_number_gt                2312
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+1.7125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.052

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl Uani 0.22505(7) 0.31168(4) 0.20433(1) 1.000 0.0286(2) . .
O1 O Uani -0.41725(17) 0.62994(10) 0.37304(4) 1.000 0.0235(4) . .
N1 N Uani 0.4008(2) 0.41509(11) 0.43830(6) 1.000 0.0219(5) . .
N2 N Uani -0.28136(19) 0.70096(11) 0.43864(5) 1.000 0.0172(4) . .
N3 N Uani 0.01242(19) 0.64367(11) 0.45932(5) 1.000 0.0171(4) . .
N4 N Uani -0.1271(2) 0.77577(12) 0.50042(5) 1.000 0.0187(4) . .
C1 C Uani 0.1834(2) 0.41228(13) 0.24469(6) 1.000 0.0212(5) . .
C2 C Uani 0.1131(3) 0.50482(14) 0.22825(6) 1.000 0.0232(5) . .
C3 C Uani 0.0808(3) 0.58327(14) 0.26073(7) 1.000 0.0234(6) . .
C4 C Uani 0.1189(2) 0.56933(13) 0.30824(6) 1.000 0.0214(5) . .
C5 C Uani 0.1892(2) 0.47543(13) 0.32515(6) 1.000 0.0185(5) . .
C6 C Uani 0.2214(2) 0.39611(14) 0.29221(6) 1.000 0.0189(5) . .
C7 C Uani 0.2379(2) 0.46079(13) 0.37557(6) 1.000 0.0181(5) . .
C8 C Uani 0.1648(2) 0.50779(13) 0.41753(6) 1.000 0.0180(5) . .
C9 C Uani 0.2692(2) 0.47759(13) 0.45495(6) 1.000 0.0192(5) . .
C10 C Uani 0.3832(2) 0.40444(13) 0.39035(6) 1.000 0.0203(5) . .
C11 C Uani 0.0050(2) 0.57186(12) 0.42362(6) 1.000 0.0177(5) . .
C12 C Uani -0.1434(2) 0.56157(13) 0.39564(6) 1.000 0.0213(5) . .
C13 C Uani -0.2806(2) 0.63208(13) 0.40361(6) 1.000 0.0185(5) . .
C14 C Uani -0.1328(2) 0.70176(12) 0.46559(6) 1.000 0.0162(5) . .
C15 C Uani -0.5489(3) 0.71027(15) 0.37650(7) 1.000 0.0233(6) . .
H4N H Uiso -0.046(3) 0.7700(16) 0.5217(7) 1.000 0.026(6) . .
H1N H Uiso 0.483(3) 0.3830(16) 0.4561(7) 1.000 0.031(6) . .
H2 H Uiso 0.08810 0.51410 0.19630 1.000 0.0280 calc R
H3 H Uiso 0.03300 0.64620 0.25050 1.000 0.0280 calc R
H4 H Uiso 0.09730 0.62350 0.32940 1.000 0.0260 calc R
H4B H Uiso -0.235(4) 0.8024(18) 0.5101(8) 1.000 0.045(7) . .
H6 H Uiso 0.26830 0.33270 0.30220 1.000 0.0230 calc R
H9 H Uiso 0.25270 0.49670 0.48640 1.000 0.0230 calc R
H10 H Uiso 0.45730 0.36550 0.37080 1.000 0.0240 calc R
H12 H Uiso -0.15150 0.51000 0.37250 1.000 0.0260 calc R
H15A H Uiso -0.609(3) 0.7081(15) 0.3461(8) 1.000 0.031(6) . .
H15B H Uiso -0.631(3) 0.6956(17) 0.4020(8) 1.000 0.036(6) . .
H15C H Uiso -0.496(3) 0.7791(18) 0.3814(7) 1.000 0.033(6) . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7489(17) . . yes
O1 C13 1.346(2) . . yes
O1 C15 1.435(2) . . yes
N1 C9 1.360(2) . . yes
N1 C10 1.367(2) . . yes
N2 C13 1.325(2) . . yes
N2 C14 1.356(2) . . yes
N3 C11 1.366(2) . . yes
N3 C14 1.337(2) . . yes
N4 C14 1.367(2) . . yes
N1 H1N 0.90(2) . . no
N4 H4N 0.86(2) . . no
N4 H4B 0.93(3) . . no
C1 C2 1.380(2) . . no
C1 C6 1.387(2) . . no
C2 C3 1.382(3) . . no
C3 C4 1.383(3) . . no
C4 C5 1.399(2) . . no
C5 C6 1.399(2) . . no
C5 C7 1.482(2) . . no
C7 C10 1.378(2) . . no
C7 C8 1.439(2) . . no
C8 C9 1.374(2) . . no
C8 C11 1.470(2) . . no
C11 C12 1.378(2) . . no
C12 C13 1.393(2) . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C6 H6 0.9300 . . no
C9 H9 0.9300 . . no
C10 H10 0.9300 . . no
C12 H12 0.9300 . . no
C15 H15A 0.97(2) . . no
C15 H15B 0.97(2) . . no
C15 H15C 0.98(2) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C15 118.25(14) . . . yes
C9 N1 C10 109.26(14) . . . yes
C13 N2 C14 114.84(14) . . . yes
C11 N3 C14 116.04(14) . . . yes
C10 N1 H1N 125.1(13) . . . no
C9 N1 H1N 125.5(13) . . . no
H4N N4 H4B 117(2) . . . no
C14 N4 H4N 117.7(14) . . . no
C14 N4 H4B 116.2(15) . . . no
C2 C1 C6 122.22(16) . . . no
Cl1 C1 C6 118.85(13) . . . yes
Cl1 C1 C2 118.93(13) . . . yes
C1 C2 C3 118.03(16) . . . no
C2 C3 C4 120.82(17) . . . no
C3 C4 C5 121.38(16) . . . no
C4 C5 C7 122.05(15) . . . no
C6 C5 C7 120.21(15) . . . no
C4 C5 C6 117.66(15) . . . no
C1 C6 C5 119.88(16) . . . no
C5 C7 C10 123.69(15) . . . no
C8 C7 C10 106.00(14) . . . no
C5 C7 C8 129.96(14) . . . no
C7 C8 C9 107.14(14) . . . no
C7 C8 C11 130.18(15) . . . no
C9 C8 C11 122.60(15) . . . no
N1 C9 C8 108.64(15) . . . yes
N1 C10 C7 108.96(14) . . . yes
N3 C11 C12 121.39(14) . . . yes
C8 C11 C12 123.21(15) . . . no
N3 C11 C8 115.40(14) . . . yes
C11 C12 C13 116.78(15) . . . no
O1 C13 N2 119.25(14) . . . yes
O1 C13 C12 116.99(15) . . . yes
N2 C13 C12 123.75(15) . . . yes
N2 C14 N4 115.78(14) . . . yes
N3 C14 N4 117.11(14) . . . yes
N2 C14 N3 126.90(15) . . . yes
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
N1 C9 H9 126.00 . . . no
C8 C9 H9 126.00 . . . no
N1 C10 H10 126.00 . . . no
C7 C10 H10 125.00 . . . no
C11 C12 H12 122.00 . . . no
C13 C12 H12 122.00 . . . no
O1 C15 H15A 104.1(12) . . . no
O1 C15 H15B 110.8(13) . . . no
O1 C15 H15C 111.9(13) . . . no
H15A C15 H15B 110.6(19) . . . no
H15A C15 H15C 110.0(17) . . . no
H15B C15 H15C 109.4(18) . . . no

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
C15 O1 C13 C12 -171.93(15) . . . . no
C15 O1 C13 N2 6.9(2) . . . . no
C9 N1 C10 C7 -0.04(19) . . . . no
C10 N1 C9 C8 0.10(18) . . . . no
C13 N2 C14 N3 2.4(2) . . . . no
C13 N2 C14 N4 176.83(15) . . . . no
C14 N2 C13 O1 -175.76(14) . . . . no
C14 N2 C13 C12 3.0(2) . . . . no
C11 N3 C14 N2 -4.2(2) . . . . no
C14 N3 C11 C8 -179.31(14) . . . . no
C14 N3 C11 C12 0.7(2) . . . . no
C11 N3 C14 N4 -178.58(14) . . . . no
Cl1 C1 C6 C5 -179.98(14) . . . . no
C2 C1 C6 C5 -0.3(2) . . . . no
C6 C1 C2 C3 0.2(3) . . . . no
Cl1 C1 C2 C3 179.86(15) . . . . no
C1 C2 C3 C4 0.4(3) . . . . no
C2 C3 C4 C5 -0.8(3) . . . . no
C3 C4 C5 C7 177.33(16) . . . . no
C3 C4 C5 C6 0.6(2) . . . . no
C4 C5 C7 C8 29.5(3) . . . . no
C4 C5 C7 C10 -142.78(17) . . . . no
C6 C5 C7 C8 -153.89(17) . . . . no
C6 C5 C7 C10 33.9(2) . . . . no
C4 C5 C6 C1 -0.1(2) . . . . no
C7 C5 C6 C1 -176.87(14) . . . . no
C5 C7 C8 C9 -173.21(16) . . . . no
C10 C7 C8 C11 -176.67(16) . . . . no
C5 C7 C10 N1 173.79(15) . . . . no
C8 C7 C10 N1 -0.02(19) . . . . no
C5 C7 C8 C11 10.1(3) . . . . no
C10 C7 C8 C9 0.07(18) . . . . no
C7 C8 C11 N3 -149.86(17) . . . . no
C7 C8 C9 N1 -0.10(19) . . . . no
C11 C8 C9 N1 176.95(14) . . . . no
C9 C8 C11 C12 -146.22(17) . . . . no
C7 C8 C11 C12 30.1(3) . . . . no
C9 C8 C11 N3 33.8(2) . . . . no
N3 C11 C12 C13 3.9(2) . . . . no
C8 C11 C12 C13 -176.08(15) . . . . no
C11 C12 C13 N2 -5.9(3) . . . . no
C11 C12 C13 O1 172.83(15) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 C15 3.588(2) . 4_545 no
Cl1 C3 3.640(2) . 7_545 no
Cl1 H3 3.1500 . 4_545 no
Cl1 H10 3.0100 . 6_455 no
Cl1 H3 3.0900 . 7_545 no
O1 C7 3.389(2) . 1_455 no
O1 C10 3.296(2) . 1_455 no
O1 C2 3.286(2) . 6_455 no
O1 H2 2.4600 . 6_455 no
N1 N4 3.030(2) . 7_545 no
N1 C14 3.337(2) . 7_545 no
N2 N4 3.141(2) . 3_466 no
N3 N4 3.126(2) . 3_566 no
N4 N2 3.141(2) . 3_566 no
N4 N3 3.126(2) . 3_466 no
N4 N1 3.030(2) . 7_555 no
N2 H15B 2.84(2) . . no
N2 H4N 2.32(2) . 3_466 no
N2 H15C 2.50(2) . . no
N3 H4B 2.21(3) . 3_566 no
N3 H9 2.7200 . . no
N4 H15B 2.78(2) . 3_566 no
N4 H1N 2.15(2) . 7_555 no
C1 C2 3.539(3) . 6_555 no
C2 O1 3.286(2) . 6_555 no
C2 C1 3.539(3) . 6_455 no
C2 C5 3.559(3) . 6_455 no
C2 C6 3.321(3) . 6_455 no
C3 Cl1 3.640(2) . 7_555 no
C4 C11 3.369(2) . . no
C4 C12 3.166(2) . . no
C5 C2 3.559(3) . 6_555 no
C5 C12 3.389(2) . . no
C6 C2 3.321(3) . 6_555 no
C7 C15 3.580(3) . 1_655 no
C7 O1 3.389(2) . 1_655 no
C7 C15 3.514(3) . 7_445 no
C8 C15 3.571(3) . 1_655 no
C9 C14 3.373(2) . 5_566 no
C10 C15 3.566(3) . 7_445 no
C10 O1 3.296(2) . 1_655 no
C11 C4 3.369(2) . . no
C12 C5 3.389(2) . . no
C12 C4 3.166(2) . . no
C14 C9 3.373(2) . 5_566 no
C14 N1 3.337(2) . 7_555 no
C15 C8 3.571(3) . 1_455 no
C15 Cl1 3.588(2) . 4_555 no
C15 C7 3.580(3) . 1_455 no
C15 C7 3.514(3) . 7_455 no
C15 C10 3.566(3) . 7_455 no
C4 H15A 2.92(2) . 1_655 no
C4 H12 2.8400 . . no
C5 H12 2.9300 . . no
C6 H10 2.8700 . . no
C6 H15A 2.97(2) . 7_445 no
C7 H12 3.0100 . . no
C7 H15C 2.96(2) . 7_445 no
C8 H4 2.9400 . . no
C8 H15B 2.89(2) . 1_655 no
C9 H4B 2.99(2) . 3_566 no
C10 H6 2.7900 . . no
C11 H4 2.8300 . . no
C12 H4 2.7300 . . no
C14 H4B 3.08(3) . 3_566 no
C14 H1N 2.60(2) . 7_555 no
C14 H9 3.0200 . 5_566 no
C15 H4N 2.89(2) . 3_466 no
C15 H6 3.1000 . 7_455 no
H4N N2 2.32(2) . 3_566 no
H4N C15 2.89(2) . 3_566 no
H4N H15B 2.29(3) . 3_566 no
H4N H1N 2.40(3) . 7_555 no
H1N N4 2.15(2) . 7_545 no
H1N C14 2.60(2) . 7_545 no
H1N H4N 2.40(3) . 7_545 no
H2 O1 2.4600 . 6_555 no
H3 Cl1 3.1500 . 4_555 no
H3 Cl1 3.0900 . 7_555 no
H4 C8 2.9400 . . no
H4 C11 2.8300 . . no
H4 C12 2.7300 . . no
H4 H15A 2.5100 . 1_655 no
H4B N3 2.21(3) . 3_466 no
H4B C9 2.99(2) . 3_466 no
H4B C14 3.08(3) . 3_466 no
H4B H9 2.5800 . 3_466 no
H6 C10 2.7900 . . no
H6 H10 2.4400 . . no
H6 C15 3.1000 . 7_445 no
H6 H15A 2.3500 . 7_445 no
H9 N3 2.7200 . . no
H9 H4B 2.5800 . 3_566 no
H9 C14 3.0200 . 5_566 no
H10 C6 2.8700 . . no
H10 H6 2.4400 . . no
H10 Cl1 3.0100 . 6_555 no
H12 C4 2.8400 . . no
H12 C5 2.9300 . . no
H12 C7 3.0100 . . no
H15A C4 2.92(2) . 1_455 no
H15A H4 2.5100 . 1_455 no
H15A C6 2.97(2) . 7_455 no
H15A H6 2.3500 . 7_455 no
H15B N2 2.84(2) . . no
H15B C8 2.89(2) . 1_455 no
H15B N4 2.78(2) . 3_466 no
H15B H4N 2.29(3) . 3_466 no
H15C N2 2.50(2) . . no
H15C C7 2.96(2) . 7_455 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N4 H4N N2 0.86(2) 2.32(2) 3.141(2) 159.3(18) 3_566 yes
N1 H1N N4 0.90(2) 2.15(2) 3.030(2) 165(2) 7_545 yes
N4 H4B N3 0.93(3) 2.21(3) 3.126(2) 174(2) 3_466 yes
C2 H2 O1 0.9300 2.4600 3.286(2) 149.00 6_555 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END

_database_code_depnum_ccdc_archive 'CCDC 955689'
