The title compound, C
10H
12N
4O
2+·2Cl
−, was synthesized by the reaction of 5-amino-8-hydroxyquinoline and cyanamide. The plane of the guanidinium group is perpendicular to the quinoline ring system, with a dihedral angle of 83.52 (10)°. N—H
Cl and O—H
Cl hydrogen bonds form a three-dimensional network.
Supporting information
CCDC reference: 236106
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.139
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
5-(8-hydroxyquinolyl)guanidine dihydrochloride
top
Crystal data top
C10H12N4O2+·2Cl− | F(000) = 1136 |
Mr = 275.14 | Dx = 1.361 Mg m−3 |
Monoclinic, C2/c | Melting point = 542–543 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.715 (2) Å | Cell parameters from 25 reflections |
b = 11.333 (2) Å | θ = 2.1–25.3° |
c = 22.720 (5) Å | µ = 0.47 mm−1 |
β = 103.30 (3)° | T = 293 K |
V = 2685.0 (10) Å3 | Prism, yellow |
Z = 8 | 0.3 × 0.25 × 0.22 mm |
Data collection top
Siemens P4 diffractometer | 1885 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
2θ/ω scans | h = 0→12 |
Absorption correction: ψ scan (XPREP in SHELXTL; Bruker, 2000) | k = 0→13 |
Tmin = 0.8, Tmax = 0.9 | l = −26→26 |
2501 measured reflections | 3 standard reflections every 97 reflections |
2366 independent reflections | intensity decay: 2.5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.09P)2 + 1.95P] where P = (Fo2 + 2Fc2)/3 |
2366 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 1.2590 (3) | 1.0302 (3) | 0.42151 (14) | 0.0341 (5) | |
H1 | 1.3457 | 1.0492 | 0.4295 | 0.041* | |
C2 | 1.1759 (3) | 1.0784 (3) | 0.37068 (14) | 0.0340 (5) | |
H2 | 1.2050 | 1.1317 | 0.3457 | 0.041* | |
C3 | 1.0491 (3) | 1.0440 (3) | 0.35888 (13) | 0.0323 (5) | |
H3 | 0.9932 | 1.0723 | 0.3242 | 0.039* | |
C4 | 1.0018 (3) | 0.9689 (3) | 0.39685 (13) | 0.0304 (4) | |
C5 | 0.8718 (3) | 0.9363 (3) | 0.38835 (13) | 0.0325 (4) | |
C6 | 0.8358 (3) | 0.8577 (3) | 0.42718 (13) | 0.0340 (5) | |
H6 | 0.7508 | 0.8332 | 0.4200 | 0.041* | |
C7 | 0.9244 (3) | 0.8139 (3) | 0.47745 (13) | 0.0316 (5) | |
H7 | 0.8974 | 0.7622 | 0.5038 | 0.038* | |
C8 | 1.0539 (3) | 0.8471 (3) | 0.48843 (12) | 0.0285 (4) | |
C9 | 1.0878 (3) | 0.9217 (3) | 0.44814 (12) | 0.0282 (4) | |
C10 | 0.7523 (3) | 0.9455 (3) | 0.28186 (13) | 0.0350 (5) | |
Cl1 | 0.07744 (8) | 0.70303 (7) | 0.33352 (3) | 0.0428 (3) | |
Cl2 | 0.46422 (8) | 0.84034 (7) | 0.37643 (4) | 0.0424 (3) | |
N1 | 1.2178 (2) | 0.9594 (2) | 0.45793 (11) | 0.0320 (4) | |
H1A | 1.2717 | 0.9341 | 0.4895 | 0.038* | |
N2 | 0.7795 (2) | 0.9870 (2) | 0.33973 (11) | 0.0336 (5) | |
H2A | 0.7381 | 1.0479 | 0.3474 | 0.040* | |
N3 | 0.6642 (2) | 1.0026 (3) | 0.24133 (12) | 0.0418 (6) | |
H3A | 0.6461 | 0.9800 | 0.2042 | 0.050* | |
H3B | 0.6252 | 1.0623 | 0.2522 | 0.050* | |
N4 | 0.8161 (3) | 0.8536 (3) | 0.26882 (13) | 0.0481 (7) | |
H4A | 0.8015 | 0.8276 | 0.2323 | 0.058* | |
H4B | 0.8724 | 0.8197 | 0.2968 | 0.058* | |
O1 | 1.14419 (19) | 0.8084 (2) | 0.53612 (9) | 0.0366 (5) | |
H1C | 1.1056 | 0.7553 | 0.5597 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0259 (9) | 0.0360 (9) | 0.0391 (9) | 0.0030 (8) | 0.0047 (8) | −0.0011 (8) |
C2 | 0.0262 (9) | 0.0367 (10) | 0.0378 (9) | 0.0021 (8) | 0.0045 (8) | 0.0004 (8) |
C3 | 0.0272 (9) | 0.0333 (9) | 0.0346 (9) | 0.0010 (8) | 0.0036 (8) | −0.0008 (8) |
C4 | 0.0259 (8) | 0.0326 (8) | 0.0309 (8) | 0.0037 (7) | 0.0032 (7) | −0.0042 (7) |
C5 | 0.0287 (8) | 0.0355 (8) | 0.0314 (8) | 0.0034 (7) | 0.0028 (7) | −0.0051 (7) |
C6 | 0.0292 (9) | 0.0397 (9) | 0.0323 (9) | −0.0013 (8) | 0.0058 (8) | −0.0023 (8) |
C7 | 0.0274 (9) | 0.0375 (9) | 0.0295 (9) | −0.0010 (8) | 0.0056 (8) | −0.0006 (8) |
C8 | 0.0258 (8) | 0.0330 (9) | 0.0262 (8) | 0.0015 (7) | 0.0047 (7) | −0.0018 (7) |
C9 | 0.0224 (7) | 0.0324 (8) | 0.0285 (7) | 0.0047 (7) | 0.0032 (6) | −0.0032 (7) |
C10 | 0.0322 (9) | 0.0394 (10) | 0.0307 (9) | 0.0059 (9) | 0.0014 (8) | −0.0037 (8) |
Cl1 | 0.0510 (5) | 0.0403 (5) | 0.0358 (4) | 0.0149 (4) | 0.0072 (3) | 0.0044 (3) |
Cl2 | 0.0532 (5) | 0.0367 (5) | 0.0358 (4) | 0.0022 (4) | 0.0071 (3) | 0.0054 (3) |
N1 | 0.0249 (8) | 0.0343 (9) | 0.0351 (8) | 0.0050 (7) | 0.0036 (7) | −0.0020 (7) |
N2 | 0.0311 (8) | 0.0365 (9) | 0.0308 (8) | 0.0060 (8) | 0.0021 (7) | −0.0068 (7) |
N3 | 0.0345 (12) | 0.0497 (14) | 0.0356 (12) | 0.0115 (11) | −0.0036 (10) | −0.0003 (11) |
N4 | 0.0510 (14) | 0.0502 (14) | 0.0364 (12) | 0.0137 (12) | −0.0037 (11) | −0.0160 (11) |
O1 | 0.0337 (10) | 0.0428 (11) | 0.0296 (10) | 0.0031 (9) | −0.0007 (8) | 0.0072 (8) |
Geometric parameters (Å, º) top
C1—N1 | 1.300 (4) | C7—H7 | 0.9300 |
C1—C2 | 1.397 (4) | C8—O1 | 1.349 (3) |
C1—H1 | 0.9300 | C8—C9 | 1.356 (4) |
C2—C3 | 1.380 (4) | C9—N1 | 1.426 (4) |
C2—H2 | 0.9300 | C10—N4 | 1.316 (4) |
C3—C4 | 1.388 (4) | C10—N3 | 1.326 (4) |
C3—H3 | 0.9300 | C10—N2 | 1.363 (4) |
C4—C5 | 1.412 (4) | N1—H1A | 0.8600 |
C4—C9 | 1.413 (4) | N2—H2A | 0.8600 |
C5—C6 | 1.370 (4) | N3—H3A | 0.8600 |
C5—N2 | 1.423 (4) | N3—H3B | 0.8600 |
C6—C7 | 1.398 (4) | N4—H4A | 0.8600 |
C6—H6 | 0.9300 | N4—H4B | 0.8600 |
C7—C8 | 1.404 (4) | O1—H1C | 0.9600 |
| | | |
N1—C1—C2 | 121.5 (3) | O1—C8—C7 | 123.6 (3) |
N1—C1—H1 | 119.3 | C9—C8—C7 | 117.1 (3) |
C2—C1—H1 | 119.3 | C8—C9—C4 | 124.5 (3) |
C3—C2—C1 | 117.6 (3) | C8—C9—N1 | 119.1 (2) |
C3—C2—H2 | 121.2 | C4—C9—N1 | 116.4 (3) |
C1—C2—H2 | 121.2 | N4—C10—N3 | 123.6 (3) |
C2—C3—C4 | 122.4 (3) | N4—C10—N2 | 118.8 (3) |
C2—C3—H3 | 118.8 | N3—C10—N2 | 117.5 (3) |
C4—C3—H3 | 118.8 | C1—N1—C9 | 123.3 (3) |
C3—C4—C5 | 124.4 (3) | C1—N1—H1A | 118.4 |
C3—C4—C9 | 118.8 (3) | C9—N1—H1A | 118.4 |
C5—C4—C9 | 116.7 (3) | C10—N2—C5 | 124.5 (3) |
C6—C5—C4 | 119.9 (3) | C10—N2—H2A | 117.8 |
C6—C5—N2 | 120.9 (3) | C5—N2—H2A | 117.8 |
C4—C5—N2 | 119.3 (3) | C10—N3—H3A | 120.0 |
C5—C6—C7 | 121.2 (3) | C10—N3—H3B | 120.0 |
C5—C6—H6 | 119.4 | H3A—N3—H3B | 120.0 |
C7—C6—H6 | 119.4 | C10—N4—H4A | 120.0 |
C6—C7—C8 | 120.5 (3) | C10—N4—H4B | 120.0 |
C6—C7—H7 | 119.7 | H4A—N4—H4B | 120.0 |
C8—C7—H7 | 119.7 | C8—O1—H1C | 109.2 |
O1—C8—C9 | 119.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1i | 0.86 | 2.43 | 3.250 (3) | 160 |
N3—H3B···Cl1i | 0.86 | 2.58 | 3.362 (3) | 152 |
N3—H3A···Cl2ii | 0.86 | 2.50 | 3.277 (3) | 150 |
N4—H4A···Cl1ii | 0.86 | 2.61 | 3.293 (3) | 137 |
N4—H4B···Cl1iii | 0.86 | 2.54 | 3.320 (3) | 152 |
O1—H1C···Cl2iv | 0.96 | 2.08 | 3.033 (2) | 170 |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1, y, −z+1/2; (iii) x+1, y, z; (iv) −x+3/2, −y+3/2, −z+1. |