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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1069.
Published online 2009 April 18. doi:  10.1107/S1600536809013816
PMCID: PMC2977749

Bis(2-amino-4,5-dimethyl­anilinium chloride) 4,5-dimethyl­benz­ene-1,2-diamine monohydrate

Abstract

The title compound, 2C8H13N2 +·2Cl·C8H12N2·H2O, is a hydrated 2:1 cocrystal of the 2-amino-4,5-dimethyl­anilinium chloride salt and the 4,5-dimethyl­benz­ene-1,2-diamine free base. An intra­molecular N—H(...)N hydrogen bond occurs in one of the organic mol­ecules. In the crystal structure, the components are linked by N—H(...)Cl, N—H(...)N, N—H(...)O and O—H(...)Cl hydrogen bonds into a layered motif.

Related literature

4,5-Dimethyl­phenyl­ene-1,2-diamine is used in the synthesis of benzimidazoles; see: El Ashry et al. (1986 [triangle]). The crystal structures of several metal complexes of 4,5-dimethyl­phenyl­ene-1,2-diamine have been reported; see: Pérez-Cabré et al. (2004 [triangle]); Eremenko et al. (2005 [triangle]); Kiskin et al. (2006 [triangle]); Malkov et al. (2003 [triangle]); Mikhailova et al. (2002 [triangle]); Redshaw et al. (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1069-scheme1.jpg

Experimental

Crystal data

  • 2C8H13N2 +·2Cl·C8H12N2·H2O
  • M r = 499.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1069-efi1.jpg
  • a = 11.7102 (5) Å
  • b = 6.0938 (3) Å
  • c = 35.948 (1) Å
  • β = 91.257 (2)°
  • V = 2564.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 123 K
  • 0.40 × 0.12 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.896, T max = 0.994
  • 16985 measured reflections
  • 5877 independent reflections
  • 3608 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.166
  • S = 1.06
  • 5877 reflections
  • 368 parameters
  • 27 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013816/hb2941sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013816/hb2941Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Colourless plates of (I) were unexpectedly isolated from the reaction of dibenzyltin dichloride (1 mmol) and 4,5-dimethylphenene-1,2-diamine in ethanol, in an attempt at synthesizing a tin complex. Atmospheric water was presumably incorporated into the crystal.

Refinement

The carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

The amino/ammonium and water H-atoms were located in a difference map, and were refined with distance restraint of N–H = 0.88 + 0.01 Å and H···H = 1.44±0.01; O–H = 0.84±0.01 Å and H···H = 1.37±0.01 Å; their Uiso values were freely refined.

Figures

Fig. 1.
The molecular structure of (I) showing 70% displacement ellipsoids Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

2C8H13N2+·2Cl·C8H12N2·H2OF(000) = 1072
Mr = 499.52Dx = 1.294 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1367 reflections
a = 11.7102 (5) Åθ = 2.3–21.3°
b = 6.0938 (3) ŵ = 0.28 mm1
c = 35.948 (1) ÅT = 123 K
β = 91.257 (2)°Plate, colourless
V = 2564.7 (2) Å30.40 × 0.12 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5877 independent reflections
Radiation source: fine-focus sealed tube3608 reflections with I > 2σ(I)
graphiteRint = 0.087
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.896, Tmax = 0.994k = −7→7
16985 measured reflectionsl = −46→46

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0711P)2] where P = (Fo2 + 2Fc2)/3
5877 reflections(Δ/σ)max = 0.001
368 parametersΔρmax = 0.47 e Å3
27 restraintsΔρmin = −0.45 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.34435 (7)−0.08992 (14)0.23602 (2)0.0211 (2)
Cl20.73644 (7)0.46400 (14)0.21359 (2)0.0195 (2)
O10.4381 (2)0.3932 (4)0.25526 (7)0.0223 (5)
H10.407 (3)0.269 (3)0.2515 (12)0.056 (16)*
H20.386 (3)0.480 (5)0.2618 (15)0.09 (2)*
N10.1622 (3)0.7021 (5)0.15983 (8)0.0221 (7)
H110.134 (3)0.828 (3)0.1521 (10)0.045 (13)*
H120.206 (3)0.723 (6)0.1798 (8)0.063 (16)*
N20.2902 (2)0.3227 (5)0.17615 (8)0.0187 (6)
H210.309 (3)0.188 (3)0.1818 (10)0.044 (13)*
H220.247 (4)0.380 (6)0.1931 (10)0.077 (18)*
N30.4870 (2)0.6160 (5)0.18456 (8)0.0182 (6)
H310.439 (2)0.508 (4)0.1786 (9)0.047 (13)*
H320.454 (2)0.696 (5)0.2021 (7)0.055 (15)*
H330.5496 (15)0.557 (4)0.1946 (8)0.020 (9)*
N40.5951 (3)1.0243 (5)0.19219 (8)0.0226 (7)
H410.623 (3)1.156 (3)0.1953 (9)0.033 (11)*
H420.547 (3)0.991 (5)0.2094 (7)0.034 (11)*
N50.6403 (2)0.4368 (5)0.29539 (7)0.0192 (6)
H510.5748 (14)0.436 (5)0.2828 (8)0.039 (12)*
H520.675 (2)0.309 (3)0.2918 (8)0.017 (9)*
H530.684 (2)0.543 (3)0.2867 (10)0.049 (14)*
N60.5083 (3)0.7947 (5)0.31996 (8)0.0225 (7)
H610.549 (3)0.828 (5)0.3006 (7)0.039 (12)*
H620.480 (3)0.914 (3)0.3300 (9)0.037 (12)*
C10.1979 (3)0.5659 (5)0.13072 (8)0.0163 (7)
C20.2533 (3)0.3666 (5)0.13923 (8)0.0164 (7)
C30.2794 (3)0.2259 (6)0.11040 (9)0.0176 (7)
H30.31580.09030.11610.021*
C40.2541 (3)0.2765 (6)0.07322 (9)0.0181 (7)
C50.2002 (3)0.4753 (6)0.06478 (9)0.0184 (7)
C60.1728 (3)0.6154 (6)0.09380 (9)0.0182 (7)
H60.13560.75010.08810.022*
C70.2850 (3)0.1172 (6)0.04304 (9)0.0240 (8)
H7A0.3161−0.01710.05430.036*
H7B0.34230.18370.02710.036*
H7C0.21660.08140.02810.036*
C80.1731 (3)0.5393 (6)0.02498 (9)0.0238 (8)
H8A0.12890.67580.02460.036*
H8B0.12850.42250.01280.036*
H8C0.24440.56100.01170.036*
C90.5147 (3)0.7433 (5)0.15144 (9)0.0165 (7)
C100.4943 (3)0.6604 (6)0.11619 (9)0.0178 (7)
H100.45770.52210.11350.021*
C110.5260 (3)0.7745 (6)0.08461 (9)0.0189 (7)
C120.5794 (3)0.9785 (6)0.08938 (9)0.0197 (7)
C130.5985 (3)1.0614 (6)0.12482 (9)0.0207 (7)
H130.63421.20060.12750.025*
C140.5672 (3)0.9480 (6)0.15672 (9)0.0185 (7)
C150.5057 (3)0.6771 (6)0.04653 (9)0.0214 (8)
H15A0.45680.54730.04850.032*
H15B0.57890.63490.03600.032*
H15C0.46810.78590.03030.032*
C160.6182 (3)1.1097 (6)0.05619 (10)0.0284 (9)
H16A0.65761.24280.06490.043*
H16B0.55171.15060.04070.043*
H16C0.67051.02080.04150.043*
C170.6155 (3)0.4633 (6)0.33487 (8)0.0166 (7)
C180.6513 (3)0.3053 (6)0.35998 (9)0.0164 (7)
H180.69240.18140.35140.020*
C190.6281 (3)0.3241 (6)0.39766 (9)0.0176 (7)
C200.5686 (3)0.5114 (6)0.40946 (8)0.0169 (7)
C210.5321 (3)0.6663 (6)0.38371 (9)0.0183 (7)
H21A0.49120.79070.39220.022*
C220.5531 (3)0.6466 (5)0.34573 (9)0.0170 (7)
C230.6664 (3)0.1477 (6)0.42444 (9)0.0226 (8)
H23A0.71830.21100.44330.034*
H23B0.70600.03210.41090.034*
H23C0.59970.08530.43660.034*
C240.5461 (3)0.5479 (6)0.45022 (9)0.0231 (8)
H24A0.49010.66610.45290.035*
H24B0.61750.58860.46320.035*
H24C0.51610.41260.46110.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0203 (4)0.0185 (4)0.0246 (4)0.0007 (3)0.0029 (3)0.0014 (3)
Cl20.0167 (4)0.0210 (4)0.0209 (4)−0.0039 (3)0.0022 (3)0.0002 (3)
O10.0174 (12)0.0246 (14)0.0250 (13)−0.0005 (12)0.0000 (10)0.0010 (11)
N10.0231 (16)0.0224 (17)0.0207 (16)0.0022 (14)−0.0007 (13)−0.0035 (13)
N20.0186 (15)0.0185 (16)0.0189 (15)−0.0029 (13)−0.0023 (12)0.0046 (12)
N30.0171 (14)0.0151 (15)0.0223 (15)−0.0023 (13)−0.0008 (12)0.0013 (12)
N40.0234 (16)0.0199 (17)0.0244 (16)−0.0070 (13)0.0001 (13)−0.0029 (13)
N50.0158 (14)0.0259 (18)0.0160 (14)0.0036 (13)−0.0005 (12)−0.0020 (12)
N60.0245 (16)0.0235 (17)0.0196 (16)0.0050 (14)0.0012 (13)0.0049 (13)
C10.0139 (15)0.0179 (18)0.0172 (16)−0.0006 (14)0.0002 (12)0.0009 (14)
C20.0139 (16)0.0182 (18)0.0169 (16)−0.0025 (13)−0.0012 (12)0.0040 (13)
C30.0126 (16)0.0172 (18)0.0229 (17)0.0018 (13)−0.0003 (13)0.0033 (14)
C40.0165 (16)0.0181 (18)0.0197 (17)−0.0043 (14)0.0017 (13)−0.0037 (14)
C50.0156 (16)0.0206 (18)0.0188 (16)−0.0032 (14)−0.0012 (13)0.0009 (14)
C60.0148 (16)0.0159 (18)0.0236 (17)−0.0010 (14)−0.0034 (13)0.0019 (14)
C70.0222 (18)0.024 (2)0.0257 (18)0.0004 (16)0.0005 (15)−0.0042 (15)
C80.0251 (18)0.026 (2)0.0203 (17)0.0016 (16)0.0028 (14)0.0003 (15)
C90.0132 (16)0.0161 (17)0.0203 (17)0.0007 (13)0.0010 (13)0.0025 (13)
C100.0101 (15)0.0176 (18)0.0257 (18)0.0018 (13)0.0007 (13)−0.0021 (14)
C110.0137 (16)0.0206 (19)0.0222 (17)0.0020 (14)−0.0004 (13)0.0008 (14)
C120.0138 (16)0.0219 (19)0.0233 (17)0.0058 (14)0.0007 (13)0.0066 (14)
C130.0148 (16)0.0168 (18)0.0305 (19)0.0019 (14)−0.0011 (14)0.0033 (15)
C140.0120 (15)0.0168 (18)0.0267 (17)0.0019 (14)−0.0008 (13)−0.0025 (14)
C150.0212 (18)0.0211 (19)0.0219 (18)0.0018 (15)0.0012 (14)−0.0011 (14)
C160.028 (2)0.028 (2)0.030 (2)−0.0002 (17)0.0019 (16)0.0093 (16)
C170.0121 (15)0.0220 (18)0.0156 (15)0.0002 (14)−0.0005 (12)−0.0016 (14)
C180.0126 (16)0.0174 (18)0.0193 (16)−0.0002 (13)0.0004 (13)−0.0028 (14)
C190.0133 (16)0.0175 (17)0.0219 (17)−0.0045 (14)−0.0023 (13)0.0019 (14)
C200.0125 (15)0.0212 (18)0.0171 (16)−0.0028 (14)0.0000 (12)−0.0022 (14)
C210.0095 (15)0.0218 (19)0.0236 (17)−0.0007 (14)0.0005 (13)−0.0037 (14)
C220.0115 (15)0.0197 (18)0.0198 (17)−0.0034 (14)0.0004 (13)0.0004 (14)
C230.0237 (18)0.022 (2)0.0220 (18)−0.0005 (15)−0.0026 (14)0.0032 (14)
C240.0235 (18)0.028 (2)0.0178 (17)0.0007 (16)0.0019 (14)−0.0021 (15)

Geometric parameters (Å, °)

O1—H10.85 (1)C8—H8A0.9800
O1—H20.85 (4)C8—H8B0.9800
N1—C11.406 (4)C8—H8C0.9800
N1—H110.88 (1)C9—C101.380 (4)
N1—H120.87 (4)C9—C141.401 (5)
N2—C21.412 (4)C10—C111.389 (4)
N2—H210.87 (1)C10—H100.9500
N2—H220.87 (4)C11—C121.400 (5)
N3—C91.463 (4)C11—C151.506 (4)
N3—H310.89 (3)C12—C131.384 (5)
N3—H320.89 (3)C12—C161.514 (5)
N3—H330.89 (1)C13—C141.395 (5)
N4—C141.390 (4)C13—H130.9500
N4—H410.88 (1)C15—H15A0.9800
N4—H420.87 (3)C15—H15B0.9800
N5—C171.464 (4)C15—H15C0.9800
N5—H510.88 (1)C16—H16A0.9800
N5—H520.89 (1)C16—H16B0.9800
N5—H530.89 (1)C16—H16C0.9800
N6—C221.388 (4)C17—C181.379 (5)
N6—H610.88 (3)C17—C221.395 (5)
N6—H620.88 (1)C18—C191.392 (4)
C1—C61.387 (4)C18—H180.9500
C1—C21.407 (5)C19—C201.407 (5)
C2—C31.384 (4)C19—C231.505 (5)
C3—C41.397 (4)C20—C211.383 (5)
C3—H30.9500C20—C241.511 (4)
C4—C51.396 (5)C21—C221.398 (4)
C4—C71.505 (4)C21—H21A0.9500
C5—C61.391 (4)C23—H23A0.9800
C5—C81.510 (4)C23—H23B0.9800
C6—H60.9500C23—H23C0.9800
C7—H7A0.9800C24—H24A0.9800
C7—H7B0.9800C24—H24B0.9800
C7—H7C0.9800C24—H24C0.9800
H1—O1—H2107.4 (17)C9—C10—C11121.5 (3)
C1—N1—H11113 (3)C9—C10—H10119.2
C1—N1—H12121 (3)C11—C10—H10119.2
H11—N1—H12110.0 (17)C10—C11—C12118.1 (3)
C2—N2—H21118 (3)C10—C11—C15120.4 (3)
C2—N2—H22114 (3)C12—C11—C15121.5 (3)
H21—N2—H22111.0 (17)C13—C12—C11120.0 (3)
C9—N3—H31110 (2)C13—C12—C16119.2 (3)
C9—N3—H32113 (2)C11—C12—C16120.9 (3)
H31—N3—H32107.1 (15)C12—C13—C14122.4 (3)
C9—N3—H33111 (2)C12—C13—H13118.8
H31—N3—H33108.4 (15)C14—C13—H13118.8
H32—N3—H33107.4 (14)N4—C14—C13121.9 (3)
C14—N4—H41120 (2)N4—C14—C9121.0 (3)
C14—N4—H42115 (2)C13—C14—C9116.9 (3)
H41—N4—H42111.9 (16)C11—C15—H15A109.5
C17—N5—H51108 (2)C11—C15—H15B109.5
C17—N5—H52110 (2)H15A—C15—H15B109.5
H51—N5—H52108.5 (15)C11—C15—H15C109.5
C17—N5—H53113 (2)H15A—C15—H15C109.5
H51—N5—H53109.2 (15)H15B—C15—H15C109.5
H52—N5—H53108.2 (14)C12—C16—H16A109.5
C22—N6—H61119 (2)C12—C16—H16B109.5
C22—N6—H62114 (2)H16A—C16—H16B109.5
H61—N6—H62110.3 (16)C12—C16—H16C109.5
C6—C1—N1121.6 (3)H16A—C16—H16C109.5
C6—C1—C2118.9 (3)H16B—C16—H16C109.5
N1—C1—C2119.4 (3)C18—C17—C22122.0 (3)
C3—C2—C1118.7 (3)C18—C17—N5119.6 (3)
C3—C2—N2121.2 (3)C22—C17—N5118.4 (3)
C1—C2—N2119.8 (3)C17—C18—C19121.1 (3)
C2—C3—C4122.3 (3)C17—C18—H18119.5
C2—C3—H3118.9C19—C18—H18119.5
C4—C3—H3118.9C18—C19—C20117.9 (3)
C3—C4—C5119.0 (3)C18—C19—C23120.1 (3)
C3—C4—C7119.9 (3)C20—C19—C23121.9 (3)
C5—C4—C7121.2 (3)C21—C20—C19120.0 (3)
C6—C5—C4118.7 (3)C21—C20—C24119.4 (3)
C6—C5—C8120.3 (3)C19—C20—C24120.6 (3)
C4—C5—C8120.9 (3)C20—C21—C22122.5 (3)
C1—C6—C5122.5 (3)C20—C21—H21A118.8
C1—C6—H6118.8C22—C21—H21A118.8
C5—C6—H6118.8N6—C22—C17121.8 (3)
C4—C7—H7A109.5N6—C22—C21121.6 (3)
C4—C7—H7B109.5C17—C22—C21116.5 (3)
H7A—C7—H7B109.5C19—C23—H23A109.5
C4—C7—H7C109.5C19—C23—H23B109.5
H7A—C7—H7C109.5H23A—C23—H23B109.5
H7B—C7—H7C109.5C19—C23—H23C109.5
C5—C8—H8A109.5H23A—C23—H23C109.5
C5—C8—H8B109.5H23B—C23—H23C109.5
H8A—C8—H8B109.5C20—C24—H24A109.5
C5—C8—H8C109.5C20—C24—H24B109.5
H8A—C8—H8C109.5H24A—C24—H24B109.5
H8B—C8—H8C109.5C20—C24—H24C109.5
C10—C9—C14121.1 (3)H24A—C24—H24C109.5
C10—C9—N3121.1 (3)H24B—C24—H24C109.5
C14—C9—N3117.8 (3)
C6—C1—C2—C3−0.9 (5)C11—C12—C13—C140.5 (5)
N1—C1—C2—C3174.7 (3)C16—C12—C13—C14−178.7 (3)
C6—C1—C2—N2173.5 (3)C12—C13—C14—N4174.6 (3)
N1—C1—C2—N2−10.9 (5)C12—C13—C14—C90.0 (5)
C1—C2—C3—C41.0 (5)C10—C9—C14—N4−175.3 (3)
N2—C2—C3—C4−173.4 (3)N3—C9—C14—N41.9 (5)
C2—C3—C4—C5−0.3 (5)C10—C9—C14—C13−0.6 (5)
C2—C3—C4—C7179.7 (3)N3—C9—C14—C13176.6 (3)
C3—C4—C5—C6−0.5 (5)C22—C17—C18—C19−1.1 (5)
C7—C4—C5—C6179.5 (3)N5—C17—C18—C19−179.3 (3)
C3—C4—C5—C8178.8 (3)C17—C18—C19—C20−1.0 (5)
C7—C4—C5—C8−1.2 (5)C17—C18—C19—C23179.0 (3)
N1—C1—C6—C5−175.3 (3)C18—C19—C20—C212.0 (5)
C2—C1—C6—C50.1 (5)C23—C19—C20—C21−178.1 (3)
C4—C5—C6—C10.6 (5)C18—C19—C20—C24−176.8 (3)
C8—C5—C6—C1−178.8 (3)C23—C19—C20—C243.2 (5)
C14—C9—C10—C110.8 (5)C19—C20—C21—C22−0.8 (5)
N3—C9—C10—C11−176.3 (3)C24—C20—C21—C22177.9 (3)
C9—C10—C11—C12−0.3 (5)C18—C17—C22—N6−173.9 (3)
C9—C10—C11—C15178.3 (3)N5—C17—C22—N64.2 (5)
C10—C11—C12—C13−0.3 (5)C18—C17—C22—C212.3 (5)
C15—C11—C12—C13−178.9 (3)N5—C17—C22—C21−179.6 (3)
C10—C11—C12—C16178.8 (3)C20—C21—C22—N6174.9 (3)
C15—C11—C12—C160.3 (5)C20—C21—C22—C17−1.3 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···Cl10.85 (2)2.37 (2)3.212 (3)172 (4)
O1—H2···Cl1i0.85 (4)2.82 (3)3.402 (3)128 (4)
O1—H2···Cl1ii0.85 (4)2.73 (4)3.331 (2)129 (3)
N1—H12···Cl1i0.88 (3)2.81 (3)3.661 (3)164 (3)
N2—H21···Cl10.87 (2)2.61 (3)3.361 (3)145 (3)
N2—H22···N10.87 (4)2.49 (4)2.810 (4)102 (3)
N2—H22···Cl1ii0.87 (4)2.79 (4)3.599 (3)155 (3)
N3—H31···N20.89 (2)2.08 (2)2.927 (4)160 (2)
N3—H32···Cl1i0.89 (3)2.22 (3)3.092 (3)168 (2)
N3—H33···Cl20.89 (2)2.35 (2)3.216 (3)167 (2)
N4—H41···Cl2i0.87 (2)2.38 (3)3.233 (3)165 (3)
N4—H42···Cl1i0.87 (3)2.63 (3)3.434 (3)155 (3)
N5—H51···O10.88 (2)1.88 (2)2.758 (3)172 (3)
N5—H52···Cl2iii0.89 (2)2.35 (2)3.242 (3)176 (2)
N5—H53···Cl20.89 (2)2.75 (3)3.176 (3)111 (2)
N5—H53···Cl2iv0.89 (2)2.73 (2)3.540 (3)153 (2)
N6—H61···Cl2iv0.88 (3)2.71 (3)3.408 (3)138 (2)
N6—H62···N1ii0.88 (2)2.45 (3)3.277 (5)156 (3)

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2941).

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