Di­chlorido­[N-(N,N-di­methyl­carbamimido­yl)-N′,N′,4-tri­methyl­benzohydrazonamide]­platinum(II) nitro­methane hemisolvate

In the title compound, [PtCl₂(C₁₃H₂₁N₅)]·0.5CH₃NO₂, the Pt^II atom is coordinated in a slightly distorted square-planar geometry by two Cl atoms and two N atoms of the bidentate ligand. The (1,3,5-tri­aza­penta­diene)Pt^II metalla ring is slightly bent and does not conjugate with the aromatic ring. In the crystal, N—H...Cl hydrogen bonds link the complex mol­ecules, forming chains along [001]. The nitromethane solvent molecule shows half-occupancy and is disordered over two sets of sites about an inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.015
• wR factor = 0.035
• Data-to-parameter ratio = 39.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H1C    ..  H1C     ..       2.11 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6 Why ?

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Why ?
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       5.91 Why ?
PLAT128_ALERT_4_G Alternate Setting for Input Space-Group     C2/c       I2/a Note
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pt1    --  Cl1     ..        8.8 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pt1    --  Cl2     ..       13.9 su
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =        100 Note
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....         O2 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         42 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Introduction

The title complex (I) was obtained in the framework of our project devoted to the intra­molecular rearrangement of carbamimidoyl­amidoxime and di­alkyl­cyanamide ligands to furnish amidrazone complexes (Bolotin et al., 2013). The luminescent properties of 1,3,5-tri­aza­penta­diene metal complexes and the catalytic activity of some related complexes have been reported in the literature (Gushchin et al., 2008; Kopylovich et al., 2011; Sarova et al., 2006).

S2. Experimental

S2.1. Synthesis and crystallization

The platinum complex was synthesized by the described method (Bolotin et al., 2013). Crystals of I suitable for X-ray diffraction were obtained by a slow evaporation of a nitro­methane solution of the complex at room temperature in air.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The solvent of crystallization (MeNO₂) was disordered over two sites about an inversion centre with equal occupancies. The NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U_iso = 1.5 U_eq(parent atom). Other hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95-0.98 Å, and U_iso = 1.2-1.5 U_eq(parent atom). The highest peak is located 0.68 Å from atom Pt1 and the deepest hole is located 0.64 Å from atom Pt1.

S3. Results and discussion

Compound I crystallizes from MeNO₂ as hemisolvate [PtCl₂(C₁₃H₂₁N₅)].0.5MeNO₂. Nitro­methane molecules incorporated in the crystals lattice are disordered over two sites with equal occupancies. The coordination polyhedron of platinum exhibits a typical square-planar geometry. All bond angles around the Pt^II center are close to 90°. The Pt–Cl distances (2.3223 (3) and 2.3279 (3) Å) are specific for the Pt^II–Cl bonds, the Pt–N_imine bond length of 1.9809 (11) Å is a characteristic value in (imine)Pt^II species, while the Pt–N_hydrazone bond length (2.0309 (11) Å) is characteristic for Pt^II–N^sp2 complexes (Orpen et al., 1989).

The C–N_imine and C–N_hydrazone bond lengths are typical C=N double bonds, equal to 1.2966 (16) Å and 1.3049 (16) Å, respectively, while the amide N–(C=N)_imine, N–(C=N)_hydrazone and the C–NMe₂ distances are close to normal single bond values [1.3826 (17), 1.3660 (17), and 1.3408 (17) Å, respectively] (Allen et al., 1987). The N–N distance of 1.4402 (16) Å is specific for a normal single N^sp2–N^sp3 bond (Allen et al., 1987).

In the molecular structure, the (1,3,5-tri­aza­penta­diene)Pt^II ring is slightly bent and does not conjugate with the aromatic ring. The dihedral angle between the mean plane of the aromatic ring C4/C10 and the atoms N1/C3/N3 is 73.76 (9)°. All bond angles in this metallacycle are close to 120°, except the (N=C)_imine–N–(C=N)_hydrazone angle, which is equal to 127.96 (11)° and the N–Pt–N angle, which is close to 90° [88.49 (5)°]. Weak inter­molecular H-bondings between the amidoxime amide group and one of the chlorine atoms were observed in the crystal structure.

Related literature

For the luminescent properties of 1,3,5-triazapentadiene metal complexes, see: Gushchin et al. (2008); Kopylovich & Pombeiro (2011); Sarova et al. (2006) and for the catalytic activity of related complexes, see: Kopylovich & Pombeiro (2011). For the synthesis of [PtCl₂(C₁₃H₂₁N₅)] and similar compounds, see: Bolotin et al. (2013). For standard bondlengths, see: Allen et al. (1987); Orpen et al. (1989).

Computing details

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: CrystalMaker (CrystalMaker Software, 2011); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008b).

Figures

Fig. 1. View of the title complex. Thermal ellipsoids are drawn at the 50% probability level. Pt atoms are pale blue, chlorine, carbon, and nitrogen atoms are green, grey, and blue, respectively. The disordered nitromethane of crystallization has been omitted for clarity.

Dichlorido[N-(N,N-dimethylcarbamimidoyl)-N',N',4-trimethylbenzohydrazonamide]platinum(II) nitromethane hemisolvate

Crystal data

[PtCl2(C13H21N5)]·0.5CH3NO2	F(000) = 2096
Mr = 543.86	Dx = 1.958 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9933 reflections
a = 20.7561 (3) Å	θ = 3.2–36.4°
b = 15.1847 (3) Å	µ = 7.91 mm^−1
c = 14.5191 (2) Å	T = 100 K
β = 126.255 (1)°	Block, yellow
V = 3690.1 (1) Å^3	0.44 × 0.29 × 0.20 mm
Z = 8

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	9015 independent reflections
Radiation source: fine-focus sealed tube	8276 reflections with I > 2σ(I)
Curved graphite crystal monochromator	Rint = 0.017
Detector resolution: 16 pixels mm^-1	θmax = 36.5°, θmin = 2.0°
ϕ scans and ω scans with κ offset	h = −34→33
Absorption correction: numerical (SADABS; Sheldrick, 2008a)	k = −25→24
Tmin = 0.130, Tmax = 0.297	l = −20→24
38976 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.035	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0133P)^2 + 5.9064P] where P = (Fo^2 + 2Fc^2)/3
9015 reflections	(Δ/σ)max = 0.002
226 parameters	Δρmax = 0.78 e Å^−3
2 restraints	Δρmin = −1.01 e Å^−3

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.

Refinement. 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 > σ(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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt1	0.086711 (3)	0.544103 (3)	0.926821 (4)	0.01177 (1)
Cl1	0.101415 (19)	0.39718 (2)	0.89820 (3)	0.01527 (5)
Cl2	0.22139 (2)	0.56194 (2)	1.00525 (4)	0.02319 (7)
N1	0.06341 (7)	0.66831 (7)	0.95151 (10)	0.01384 (18)
N2	0.10725 (7)	0.74645 (8)	0.96392 (11)	0.0178 (2)
N3	−0.05540 (7)	0.62871 (8)	0.92740 (10)	0.01448 (18)
H3N	−0.0805	0.6409	0.9571	0.022*
N4	−0.15323 (7)	0.52601 (8)	0.81191 (10)	0.01497 (19)
N5	−0.02759 (7)	0.51555 (8)	0.84918 (10)	0.01401 (18)
H5N	−0.0494	0.4762	0.7988	0.021*
C1	0.11579 (9)	0.75208 (11)	0.87141 (14)	0.0222 (3)
H1A	0.1448	0.7003	0.8734	0.033*
H1B	0.1455	0.8055	0.8806	0.033*
H1C	0.0628	0.7542	0.7980	0.033*
C2	0.18337 (9)	0.75253 (11)	1.07686 (14)	0.0223 (3)
H2A	0.1735	0.7596	1.1346	0.033*
H2B	0.2134	0.8034	1.0793	0.033*
H2C	0.2143	0.6987	1.0925	0.033*
C3	0.00349 (8)	0.68722 (8)	0.95483 (11)	0.01326 (19)
C4	−0.00996 (8)	0.77467 (9)	0.98743 (11)	0.0143 (2)
C5	0.03328 (10)	0.80236 (10)	1.10020 (13)	0.0214 (3)
H5A	0.0757	0.7671	1.1591	0.026*
C6	0.01455 (10)	0.88207 (11)	1.12719 (14)	0.0241 (3)
H6	0.0446	0.9005	1.2047	0.029*
C7	−0.04716 (9)	0.93496 (10)	1.04312 (14)	0.0204 (3)
C8	−0.06930 (11)	1.01952 (11)	1.07194 (18)	0.0287 (3)
H8A	−0.1182	1.0107	1.0665	0.043*
H8B	−0.0783	1.0656	1.0182	0.043*
H8C	−0.0258	1.0374	1.1499	0.043*
C9	−0.09025 (9)	0.90607 (10)	0.93054 (14)	0.0220 (3)
H9	−0.1323	0.9416	0.8715	0.026*
C10	−0.07310 (9)	0.82650 (10)	0.90270 (13)	0.0196 (2)
H10	−0.1045	0.8072	0.8255	0.023*
C11	−0.07838 (8)	0.55407 (8)	0.86030 (11)	0.01253 (19)
C12	−0.17809 (9)	0.43894 (9)	0.76070 (13)	0.0182 (2)
H12A	−0.2021	0.4431	0.6790	0.027*
H12B	−0.2174	0.4151	0.7709	0.027*
H12C	−0.1315	0.3999	0.7977	0.027*
C13	−0.21699 (8)	0.58213 (10)	0.79291 (13)	0.0197 (2)
H13A	−0.2321	0.5628	0.8421	0.030*
H13B	−0.2634	0.5781	0.7127	0.030*
H13C	−0.1984	0.6433	0.8111	0.030*
O1	0.23109 (19)	0.25839 (19)	0.8531 (2)	0.0342 (6)	0.50
N6	0.24020 (19)	0.2509 (2)	0.9450 (3)	0.0313 (6)	0.50
C14	0.1897 (11)	0.1872 (12)	0.958 (2)	0.0371 (7)	0.50
H14A	0.1352	0.1861	0.8870	0.056*	0.50
H14B	0.1883	0.2062	1.0211	0.056*	0.50
H14C	0.2129	0.1280	0.9737	0.056*	0.50
O2	0.1983 (8)	0.1969 (8)	0.9556 (13)	0.0371 (7)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01165 (2)	0.01170 (2)	0.01451 (2)	0.00007 (1)	0.00913 (2)	−0.00061 (1)
Cl1	0.01681 (12)	0.01324 (12)	0.01993 (12)	0.00183 (10)	0.01316 (11)	0.00001 (10)
Cl2	0.01519 (13)	0.02011 (15)	0.03501 (18)	−0.00179 (11)	0.01526 (14)	−0.00348 (13)
N1	0.0138 (4)	0.0127 (4)	0.0187 (5)	−0.0007 (3)	0.0116 (4)	−0.0007 (4)
N2	0.0186 (5)	0.0140 (5)	0.0267 (6)	−0.0036 (4)	0.0167 (5)	−0.0011 (4)
N3	0.0164 (4)	0.0130 (4)	0.0197 (5)	−0.0019 (4)	0.0138 (4)	−0.0030 (4)
N4	0.0124 (4)	0.0142 (5)	0.0196 (5)	−0.0008 (3)	0.0102 (4)	−0.0019 (4)
N5	0.0132 (4)	0.0136 (5)	0.0165 (4)	−0.0017 (4)	0.0095 (4)	−0.0027 (4)
C1	0.0186 (6)	0.0260 (7)	0.0252 (6)	−0.0016 (5)	0.0146 (5)	0.0058 (5)
C2	0.0220 (6)	0.0211 (6)	0.0266 (7)	−0.0084 (5)	0.0159 (6)	−0.0085 (5)
C3	0.0149 (5)	0.0120 (5)	0.0158 (5)	−0.0003 (4)	0.0106 (4)	−0.0001 (4)
C4	0.0155 (5)	0.0120 (5)	0.0192 (5)	−0.0003 (4)	0.0124 (5)	−0.0009 (4)
C5	0.0278 (7)	0.0177 (6)	0.0187 (6)	0.0067 (5)	0.0137 (5)	0.0000 (5)
C6	0.0300 (7)	0.0202 (7)	0.0243 (6)	0.0044 (5)	0.0172 (6)	−0.0040 (5)
C7	0.0229 (6)	0.0132 (5)	0.0346 (7)	0.0003 (5)	0.0222 (6)	−0.0019 (5)
C8	0.0349 (8)	0.0158 (6)	0.0492 (10)	0.0023 (6)	0.0326 (8)	−0.0035 (6)
C9	0.0180 (6)	0.0179 (6)	0.0303 (7)	0.0045 (5)	0.0144 (6)	0.0018 (5)
C10	0.0165 (5)	0.0180 (6)	0.0226 (6)	0.0025 (5)	0.0107 (5)	−0.0013 (5)
C11	0.0133 (5)	0.0117 (5)	0.0146 (5)	0.0000 (4)	0.0094 (4)	0.0005 (4)
C12	0.0175 (5)	0.0166 (6)	0.0221 (6)	−0.0038 (4)	0.0126 (5)	−0.0042 (5)
C13	0.0138 (5)	0.0198 (6)	0.0246 (6)	0.0040 (4)	0.0107 (5)	0.0023 (5)
O1	0.0462 (16)	0.0301 (13)	0.0322 (13)	0.0129 (12)	0.0263 (13)	0.0062 (10)
N6	0.0300 (14)	0.0254 (14)	0.0396 (16)	0.0101 (11)	0.0211 (13)	0.0053 (12)
C14	0.032 (3)	0.028 (3)	0.0494 (12)	−0.0033 (15)	0.0232 (15)	0.0019 (18)
O2	0.032 (3)	0.028 (3)	0.0494 (12)	−0.0033 (15)	0.0232 (15)	0.0019 (18)

Geometric parameters (Å, º)

Pt1—N5	1.9809 (11)	C4—C10	1.3941 (19)
Pt1—N1	2.0309 (11)	C5—C6	1.396 (2)
Pt1—Cl1	2.3223 (3)	C5—H5A	0.9500
Pt1—Cl2	2.3279 (3)	C6—C7	1.388 (2)
N1—C3	1.3049 (16)	C6—H6	0.9500
N1—N2	1.4402 (16)	C7—C9	1.391 (2)
N2—C1	1.4576 (19)	C7—C8	1.504 (2)
N2—C2	1.459 (2)	C8—H8A	0.9800
N3—C3	1.3660 (17)	C8—H8B	0.9800
N3—C11	1.3826 (17)	C8—H8C	0.9800
N3—H3N	0.8702	C9—C10	1.386 (2)
N4—C11	1.3408 (17)	C9—H9	0.9500
N4—C12	1.4537 (18)	C10—H10	0.9500
N4—C13	1.4567 (18)	C12—H12A	0.9800
N5—C11	1.2966 (16)	C12—H12B	0.9800
N5—H5N	0.8399	C12—H12C	0.9800
C1—H1A	0.9800	C13—H13A	0.9800
C1—H1B	0.9800	C13—H13B	0.9800
C1—H1C	0.9800	C13—H13C	0.9800
C2—H2A	0.9800	O1—N6	1.237 (3)
C2—H2B	0.9800	N6—C14	1.518 (8)
C2—H2C	0.9800	C14—H14A	0.9800
C3—C4	1.4904 (18)	C14—H14B	0.9800
C4—C5	1.3875 (19)	C14—H14C	0.9800
N5—Pt1—N1	88.49 (5)	C10—C4—C3	118.53 (12)
N5—Pt1—Cl1	85.86 (3)	C4—C5—C6	120.05 (14)
N1—Pt1—Cl1	173.69 (3)	C4—C5—H5A	120.0
N5—Pt1—Cl2	172.48 (3)	C6—C5—H5A	120.0
N1—Pt1—Cl2	98.51 (3)	C7—C6—C5	121.33 (14)
Cl1—Pt1—Cl2	87.274 (12)	C7—C6—H6	119.3
C3—N1—N2	111.07 (11)	C5—C6—H6	119.3
C3—N1—Pt1	122.86 (9)	C6—C7—C9	117.95 (13)
N2—N1—Pt1	126.04 (8)	C6—C7—C8	121.61 (15)
N1—N2—C1	110.19 (11)	C9—C7—C8	120.41 (15)
N1—N2—C2	112.14 (11)	C7—C8—H8A	109.5
C1—N2—C2	113.01 (11)	C7—C8—H8B	109.5
C3—N3—C11	127.96 (11)	H8A—C8—H8B	109.5
C3—N3—H3N	114.3	C7—C8—H8C	109.5
C11—N3—H3N	117.7	H8A—C8—H8C	109.5
C11—N4—C12	120.52 (11)	H8B—C8—H8C	109.5
C11—N4—C13	123.69 (12)	C10—C9—C7	121.34 (14)
C12—N4—C13	115.29 (11)	C10—C9—H9	119.3
C11—N5—Pt1	128.23 (9)	C7—C9—H9	119.3
C11—N5—H5N	111.7	C9—C10—C4	120.30 (14)
Pt1—N5—H5N	119.9	C9—C10—H10	119.9
N2—C1—H1A	109.5	C4—C10—H10	119.9
N2—C1—H1B	109.5	N5—C11—N4	124.54 (12)
H1A—C1—H1B	109.5	N5—C11—N3	119.36 (12)
N2—C1—H1C	109.5	N4—C11—N3	116.09 (11)
H1A—C1—H1C	109.5	N4—C12—H12A	109.5
H1B—C1—H1C	109.5	N4—C12—H12B	109.5
N2—C2—H2A	109.5	H12A—C12—H12B	109.5
N2—C2—H2B	109.5	N4—C12—H12C	109.5
H2A—C2—H2B	109.5	H12A—C12—H12C	109.5
N2—C2—H2C	109.5	H12B—C12—H12C	109.5
H2A—C2—H2C	109.5	N4—C13—H13A	109.5
H2B—C2—H2C	109.5	N4—C13—H13B	109.5
N1—C3—N3	123.64 (12)	H13A—C13—H13B	109.5
N1—C3—C4	124.71 (12)	N4—C13—H13C	109.5
N3—C3—C4	111.65 (11)	H13A—C13—H13C	109.5
C5—C4—C10	118.99 (13)	H13B—C13—H13C	109.5
C5—C4—C3	122.20 (12)	O1—N6—C14	121.0 (10)
N5—Pt1—N1—C3	24.61 (11)	N3—C3—C4—C10	−70.06 (15)
Cl2—Pt1—N1—C3	−158.15 (10)	C10—C4—C5—C6	−1.5 (2)
N5—Pt1—N1—N2	−153.35 (11)	C3—C4—C5—C6	−175.32 (14)
Cl2—Pt1—N1—N2	23.89 (11)	C4—C5—C6—C7	0.2 (3)
C3—N1—N2—C1	−127.66 (12)	C5—C6—C7—C9	0.2 (2)
Pt1—N1—N2—C1	50.50 (15)	C5—C6—C7—C8	178.10 (16)
C3—N1—N2—C2	105.52 (13)	C6—C7—C9—C10	0.8 (2)
Pt1—N1—N2—C2	−76.31 (14)	C8—C7—C9—C10	−177.14 (15)
N1—Pt1—N5—C11	−23.40 (12)	C7—C9—C10—C4	−2.2 (2)
Cl1—Pt1—N5—C11	153.79 (12)	C5—C4—C10—C9	2.5 (2)
N2—N1—C3—N3	169.27 (12)	C3—C4—C10—C9	176.52 (13)
Pt1—N1—C3—N3	−8.97 (18)	Pt1—N5—C11—N4	−173.99 (10)
N2—N1—C3—C4	−10.04 (18)	Pt1—N5—C11—N3	5.04 (18)
Pt1—N1—C3—C4	171.73 (9)	C12—N4—C11—N5	12.4 (2)
C11—N3—C3—N1	−22.1 (2)	C13—N4—C11—N5	−159.13 (13)
C11—N3—C3—C4	157.24 (12)	C12—N4—C11—N3	−166.66 (12)
N1—C3—C4—C5	−76.83 (18)	C13—N4—C11—N3	21.81 (19)
N3—C3—C4—C5	103.79 (15)	C3—N3—C11—N5	24.5 (2)
N1—C3—C4—C10	109.32 (16)	C3—N3—C11—N4	−156.34 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl1^i	0.87	2.45	3.2154 (11)	147
N5—H5N···Cl1^ii	0.84	2.67	3.4598 (12)	157

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