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The asymmetric unit of the title compound, C9H12ClN5O, contains one cation, one anion, and one water mol­ecule. Inter­molecular N—H...N, N—H...O, N—H...Cl and O—H...Cl hydrogen bonds seem to be effective in the stabilization of the crystal structure, resulting in the formation of a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038475/hk2125sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038475/hk2125Isup2.hkl
Contains datablock I

CCDC reference: 609293

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.077
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,6-Diamino-4-phenyltriazinium chloride monohydrate top
Crystal data top
C9H10N5+·Cl·H2OF(000) = 504
Mr = 241.69Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.4122 (9) ÅCell parameters from 870 reflections
b = 5.0193 (5) Åθ = 3–27°
c = 26.333 (3) ŵ = 0.33 mm1
β = 93.486 (2)°T = 294 K
V = 1109.8 (2) Å3Prism, light orange
Z = 40.2 × 0.16 × 0.14 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2414 independent reflections
Radiation source: fine-focus sealed tube1847 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 1010
Tmin = 0.937, Tmax = 0.957k = 56
8092 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.077H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.01P)2 + 0.65P]
where P = (Fo2 + 2Fc2)/3
2414 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.51060 (6)0.52348 (10)0.088240 (19)0.05226 (15)
N10.88568 (16)0.2415 (3)0.03843 (5)0.0384 (3)
C20.95214 (19)0.3815 (4)0.07776 (6)0.0373 (4)
N30.92395 (16)0.3437 (3)0.12782 (5)0.0403 (4)
C40.82724 (19)0.1500 (4)0.13758 (6)0.0364 (4)
N50.76133 (16)0.0068 (3)0.09999 (5)0.0371 (3)
H30.69510.13020.10820.045*
C60.78831 (19)0.0465 (4)0.05028 (6)0.0365 (4)
N71.05145 (17)0.5747 (3)0.06818 (5)0.0455 (4)
H11.06670.59880.03610.055*
H21.09580.66140.09390.055*
N80.71620 (18)0.1019 (3)0.01495 (5)0.0485 (4)
H50.64510.21100.02550.058*
H40.72030.07230.01750.058*
C90.78750 (19)0.1020 (4)0.19086 (6)0.0383 (4)
C100.8506 (2)0.2743 (4)0.22784 (7)0.0492 (5)
H10A0.91720.41200.21880.059*
C110.8150 (2)0.2429 (5)0.27824 (7)0.0558 (5)
H11A0.85670.36060.30290.067*
C120.7185 (2)0.0385 (5)0.29162 (7)0.0541 (5)
H12A0.69480.01690.32540.065*
C130.6563 (3)0.1348 (5)0.25530 (7)0.0593 (6)
H13A0.59110.27370.26470.071*
C140.6900 (2)0.1043 (4)0.20473 (7)0.0519 (5)
H14A0.64730.22190.18030.062*
O10.72180 (16)0.9912 (3)0.90463 (5)0.0556 (4)
H60.64201.10020.90100.067*
H70.65010.85960.89270.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0510 (3)0.0463 (3)0.0606 (3)0.0062 (2)0.0128 (2)0.0000 (2)
N10.0409 (8)0.0430 (9)0.0318 (7)0.0058 (7)0.0062 (6)0.0020 (7)
C20.0337 (8)0.0433 (10)0.0353 (8)0.0005 (8)0.0054 (7)0.0043 (8)
N30.0402 (8)0.0496 (9)0.0315 (7)0.0059 (7)0.0055 (6)0.0019 (7)
C40.0349 (8)0.0408 (10)0.0336 (8)0.0042 (8)0.0038 (7)0.0035 (8)
N50.0413 (7)0.0374 (8)0.0335 (7)0.0047 (7)0.0090 (6)0.0030 (6)
C60.0376 (8)0.0390 (10)0.0333 (8)0.0014 (8)0.0055 (7)0.0027 (8)
N70.0468 (8)0.0544 (10)0.0358 (7)0.0141 (8)0.0053 (6)0.0007 (7)
N80.0589 (10)0.0530 (10)0.0340 (8)0.0155 (8)0.0053 (7)0.0000 (7)
C90.0381 (9)0.0456 (11)0.0318 (8)0.0034 (8)0.0075 (7)0.0050 (8)
C100.0551 (11)0.0554 (13)0.0375 (9)0.0076 (10)0.0057 (8)0.0039 (9)
C110.0646 (13)0.0683 (15)0.0347 (10)0.0026 (12)0.0037 (9)0.0017 (10)
C120.0566 (11)0.0720 (15)0.0346 (9)0.0085 (11)0.0106 (8)0.0102 (10)
C130.0695 (14)0.0638 (14)0.0462 (11)0.0119 (12)0.0177 (10)0.0112 (11)
C140.0617 (12)0.0550 (13)0.0398 (10)0.0102 (10)0.0099 (9)0.0004 (9)
O10.0513 (7)0.0518 (9)0.0630 (8)0.0044 (7)0.0010 (6)0.0025 (7)
Geometric parameters (Å, º) top
N1—C61.325 (2)C9—C101.384 (3)
N1—C21.345 (2)C9—C141.383 (3)
C2—N71.314 (2)C10—C111.387 (2)
C2—N31.367 (2)C10—H10A0.9300
N3—C41.303 (2)C11—C121.368 (3)
C4—N51.356 (2)C11—H11A0.9300
C4—C91.482 (2)C12—C131.373 (3)
N5—C61.3686 (19)C12—H12A0.9300
N5—H30.8692C13—C141.387 (2)
C6—N81.312 (2)C13—H13A0.9300
N7—H10.8696C14—H14A0.9300
N7—H20.8693O1—H60.8666
N8—H50.8692O1—H70.9359
N8—H40.8692
C6—N1—C2115.99 (14)C10—C9—C14119.34 (16)
N7—C2—N1118.49 (15)C10—C9—C4117.77 (16)
N7—C2—N3115.92 (16)C14—C9—C4122.89 (17)
N1—C2—N3125.58 (16)C9—C10—C11120.45 (19)
C4—N3—C2116.15 (15)C9—C10—H10A119.8
N3—C4—N5121.43 (15)C11—C10—H10A119.8
N3—C4—C9119.16 (16)C12—C11—C10119.8 (2)
N5—C4—C9119.41 (15)C12—C11—H11A120.1
C4—N5—C6120.01 (15)C10—C11—H11A120.1
C4—N5—H3118.1C11—C12—C13120.18 (17)
C6—N5—H3121.6C11—C12—H12A119.9
N8—C6—N1121.21 (15)C13—C12—H12A119.9
N8—C6—N5118.09 (16)C12—C13—C14120.5 (2)
N1—C6—N5120.70 (15)C12—C13—H13A119.7
C2—N7—H1115.0C14—C13—H13A119.7
C2—N7—H2117.9C13—C14—C9119.68 (19)
H1—N7—H2127.1C13—C14—H14A120.2
C6—N8—H5115.3C9—C14—H14A120.2
C6—N8—H4123.7H6—O1—H786.0
H5—N8—H4119.5
C6—N1—C2—N7179.05 (16)N3—C4—C9—C102.7 (2)
C6—N1—C2—N31.9 (3)N5—C4—C9—C10176.78 (16)
N7—C2—N3—C4179.10 (16)N3—C4—C9—C14177.89 (17)
N1—C2—N3—C41.9 (3)N5—C4—C9—C142.7 (3)
C2—N3—C4—N51.1 (2)C14—C9—C10—C110.8 (3)
C2—N3—C4—C9178.29 (15)C4—C9—C10—C11178.67 (18)
N3—C4—N5—C63.9 (2)C9—C10—C11—C120.8 (3)
C9—C4—N5—C6175.53 (15)C10—C11—C12—C130.2 (3)
C2—N1—C6—N8179.62 (16)C11—C12—C13—C140.3 (3)
C2—N1—C6—N51.0 (2)C12—C13—C14—C90.2 (3)
C4—N5—C6—N8176.75 (15)C10—C9—C14—C130.3 (3)
C4—N5—C6—N13.8 (2)C4—C9—C14—C13179.13 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H1···N1i0.872.183.031 (2)166
N7—H2···O1ii0.872.322.955 (2)130
N5—H3···Cl1iii0.872.373.166 (2)153
N8—H4···O1iv0.872.082.945 (2)178
N8—H5···Cl1iii0.872.453.264 (2)156
O1—H6···Cl1v0.872.313.136 (2)159
O1—H7···Cl1vi0.942.423.252 (2)148
Symmetry codes: (i) x+2, y+1, z; (ii) x+2, y+2, z+1; (iii) x, y1, z; (iv) x, y1, z1; (v) x+1, y+2, z+1; (vi) x+1, y+1, z+1.
 

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