organic papers
o1070
Daniel E. Lynchet al. C9H11N3H2O2Cl DOI: 10.1107/S1600536802015878 Acta Cryst.(2002). E58, o1070±o1071Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
8-Hydrazinoquinoline dihydrochloride
hydrate
Daniel E. Lyncha* and Ian McClenaghanb
aSchool of Science and the Environment,
Coventry University, Coventry CV1 5FB, United Kingdom, andbKey Organics Ltd, Highfield Industrial Estate, Camelford, Cornwall PL32 9QZ, United Kingdom
Correspondence e-mail: apx106@coventry.ac.uk
Key indicators Single-crystal X-ray study
T= 150 K
Mean(C±C) = 0.002 AÊ
Rfactor = 0.038
wRfactor = 0.104
Data-to-parameter ratio = 15.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The structure of the title compound, C9H11N32ClH2O,
comprises a planar cation containing two quaternary N atoms, packed in the solid-state with two Clÿ anions and one water
molecule. Each component is involved in the hydrogen-bonding network, with one Clÿ anion and the O atom both
being involved in three-centre associations, while the second Clÿanion is involved in a four-centre association.
Experimental
The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.
Crystal data
C9H11N3ÿ2ClÿH2O
Mr= 250.12
Triclinic,P1 a= 6.9716 (14) AÊ b= 8.9866 (18) AÊ c= 9.986 (2) AÊ
= 70.04 (3) = 89.20 (3) = 69.60 (3)
V= 547.2 (3) AÊ3
Z= 2
Dx= 1.518 Mg mÿ3
MoKradiation Cell parameters from 3835
re¯ections
= 2.9±27.5 = 0.57 mmÿ1
T= 150 (2) K Plate, colourless 0.400.300.10 mm
Data collection
Bruker±Nonius KappaCCD area-detector diffractometer
'and!scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995) Tmin= 0.804,Tmax= 0.945
7519 measured re¯ections
2465 independent re¯ections 2168 re¯ections withI> 2(I) Rint= 0.075
max= 27.5
h=ÿ9!9 k=ÿ11!11 l=ÿ12!12
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.038
wR(F2) = 0.104
S= 1.04 2465 re¯ections 164 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.0551P)2
+ 0.1837P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.32 e AÊÿ3
min=ÿ0.60 e AÊÿ3
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
N1ÐH1 O1Wi 0.78 (2) 2.05 (2) 2.817 (2) 165 (2)
N81ÐH81 Cl1ii 0.91 (2) 2.32 (2) 3.1983 (16) 164.5 (18)
N82ÐH82 Cl2ii 0.91 (2) 2.25 (2) 3.1476 (18) 169.8 (18)
N82ÐH83 O1Wiii 0.87 (2) 1.94 (2) 2.808 (2) 178.7 (19)
N82ÐH84 Cl2iv 0.89 (3) 2.39 (3) 3.1805 (17) 149.1 (19)
O1WÐH1W Cl1v 0.84 (3) 2.21 (3) 3.0348 (17) 164 (2)
O1WÐH2W Cl2iii 0.76 (3) 2.47 (3) 3.180 (2) 158 (2)
Symmetry codes: (i)x;y;zÿ1; (ii)xÿ1;y;z; (iii)ÿx;1ÿy;1ÿz; (iv)ÿx;1ÿy;ÿz; (v) 1ÿx;ÿy;1ÿz.
All aromatic H atoms were included in the re®nement, at calcu-lated positions, as riding models with CÐH set to 0.95 AÊ. All H atoms involved in the hydrogen-bonding network were located in difference syntheses and both positional and displacement parameters were re®ned.
Data collection: DENZO (Otwinowski & Minor, 1997) and
COLLECT(Hooft, 1998); cell re®nement:DENZOandCOLLECT; data reduction:DENZOandCOLLECT; program(s) used to solve structure:SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
PLATON-97 (Spek, 1997); software used to prepare material for publication:SHELXL97.
The authors thank the EPSRC National Crystallography Service (Southampton).
References
Blessing, R. H. (1995).Acta Cryst.A51, 33±37.
Hooft, R. (1998).COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307±326. London: Academic Press.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Spek, A. L. (1997).PLATON-97. Version of May 1997. University of Utrecht, The Netherlands.
Figure 1
supporting information
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Acta Cryst. (2002). E58, o1070–o1071supporting information
Acta Cryst. (2002). E58, o1070–o1071 [doi:10.1107/S1600536802015878]
8-Hydrazinoquinoline dihydrochloride hydrate
Daniel E. Lynch and Ian McClenaghan
S1. Comment
no comment
S2. Experimental
The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.
S3. Refinement
All aromatic H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å.
All H atoms involved in the hydrogen-bonding network were located on difference syntheses and both positional and
Figure 1
Molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids.
8-Hydrazinoquinoline dihydrochloride hydrate
Crystal data
C9H11N3·H2O·2Cl
Mr = 250.12
Triclinic, P1 Hall symbol: -P 1
a = 6.9716 (14) Å
b = 8.9866 (18) Å
c = 9.986 (2) Å
α = 70.04 (3)°
β = 89.20 (3)°
γ = 69.60 (3)°
V = 547.2 (3) Å3
Z = 2
F(000) = 260
Dx = 1.518 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3835 reflections
θ = 2.9–27.5°
µ = 0.57 mm−1
supporting information
sup-3
Acta Cryst. (2002). E58, o1070–o1071Data collection
Bruker-Nonius KappaCCD area-detector diffractometer
Radiation source: Bruker Nonius FR591 rotating-anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995)
Tmin = 0.804, Tmax = 0.945 7519 measured reflections 2465 independent reflections 2168 reflections with I > 2σ(I)
Rint = 0.075
θmax = 27.5°, θmin = 3.1°
h = −9→9
k = −11→11
l = −12→12
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.038
wR(F2) = 0.104
S = 1.04 2465 reflections 164 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0551P)2 + 0.1837P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.32 e Å−3 Δρmin = −0.60 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
N1 0.1739 (2) 0.07021 (18) 0.21676 (16) 0.0155 (3)
H1 0.134 (3) 0.116 (3) 0.135 (3) 0.030 (6)*
C2 0.3176 (3) −0.0843 (2) 0.25755 (19) 0.0191 (4)
H2 0.3641 −0.1364 0.1888 0.024*
C3 0.4012 (3) −0.1711 (2) 0.40145 (19) 0.0211 (4)
H3 0.4996 −0.2840 0.4318 0.026*
C4 0.3395 (3) −0.0915 (2) 0.49820 (18) 0.0188 (4)
H4 0.3994 −0.1481 0.5955 0.023*
C5 0.1176 (3) 0.1629 (2) 0.54967 (17) 0.0185 (4)
H5 0.1748 0.1122 0.6476 0.023*
C6 −0.0323 (3) 0.3219 (2) 0.50005 (18) 0.0185 (4)
H6 −0.0776 0.3813 0.5640 0.023*
C7 −0.1209 (3) 0.3991 (2) 0.35551 (18) 0.0170 (3)
H7 −0.2248 0.5097 0.3237 0.021*
C8 −0.0597 (2) 0.31715 (19) 0.26010 (16) 0.0129 (3)
N81 −0.1340 (2) 0.38149 (17) 0.11329 (14) 0.0154 (3)
H81 −0.188 (3) 0.313 (3) 0.091 (2) 0.024 (5)*
N82 −0.2880 (2) 0.54946 (17) 0.06257 (16) 0.0153 (3)
H82 −0.405 (4) 0.551 (3) 0.105 (2) 0.026 (5)*
H83 −0.233 (3) 0.620 (3) 0.070 (2) 0.017 (5)*
H84 −0.319 (4) 0.578 (3) −0.031 (3) 0.034 (6)*
C9 0.1006 (2) 0.15379 (19) 0.30938 (16) 0.0135 (3)
C10 0.1875 (2) 0.0741 (2) 0.45477 (17) 0.0155 (3)
Cl2 0.33779 (6) 0.50675 (5) 0.23075 (4) 0.01915 (14)
O1W 0.1078 (2) 0.22369 (16) 0.91537 (13) 0.0191 (3)
H1W 0.159 (4) 0.134 (4) 0.896 (3) 0.051 (8)*
H2W 0.001 (4) 0.266 (3) 0.875 (3) 0.033 (7)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
N1 0.0183 (7) 0.0164 (7) 0.0118 (7) −0.0062 (6) −0.0005 (5) −0.0049 (6)
C2 0.0201 (9) 0.0168 (8) 0.0209 (9) −0.0056 (7) 0.0025 (7) −0.0084 (7)
C3 0.0182 (8) 0.0153 (8) 0.0237 (9) −0.0037 (7) −0.0016 (7) −0.0022 (7)
C4 0.0185 (8) 0.0199 (8) 0.0157 (8) −0.0097 (7) −0.0028 (6) −0.0008 (7)
C5 0.0234 (9) 0.0257 (9) 0.0102 (7) −0.0143 (7) −0.0004 (6) −0.0055 (7)
C6 0.0247 (9) 0.0242 (9) 0.0139 (8) −0.0139 (7) 0.0046 (6) −0.0109 (7)
C7 0.0193 (8) 0.0168 (8) 0.0169 (8) −0.0070 (7) 0.0013 (6) −0.0081 (7)
C8 0.0164 (8) 0.0136 (7) 0.0102 (7) −0.0078 (6) 0.0000 (6) −0.0038 (6)
N81 0.0203 (7) 0.0120 (6) 0.0112 (7) −0.0016 (5) −0.0034 (5) −0.0053 (5)
N82 0.0178 (8) 0.0126 (7) 0.0131 (7) −0.0026 (6) −0.0018 (6) −0.0044 (6)
C9 0.0160 (8) 0.0151 (8) 0.0116 (7) −0.0080 (6) 0.0011 (6) −0.0052 (6)
C10 0.0180 (8) 0.0184 (8) 0.0122 (7) −0.0111 (6) −0.0013 (6) −0.0031 (6)
Cl1 0.0258 (3) 0.0132 (2) 0.0176 (2) −0.00356 (17) −0.00399 (16) −0.00546 (17) Cl2 0.0202 (2) 0.0218 (2) 0.0137 (2) −0.00540 (17) 0.00096 (16) −0.00665 (17)
O1W 0.0211 (7) 0.0165 (6) 0.0183 (6) −0.0021 (5) −0.0021 (5) −0.0091 (5)
Geometric parameters (Å, º)
N1—C2 1.325 (2) C6—H6 0.95
N1—C9 1.369 (2) C7—C8 1.371 (2)
N1—H1 0.78 (2) C7—H7 0.95
C2—C3 1.398 (3) C8—N81 1.409 (2)
C2—H2 0.95 C8—C9 1.423 (2)
C3—C4 1.370 (3) N81—N82 1.432 (2)
C3—H3 0.95 N81—H81 0.91 (2)
C4—C10 1.414 (2) N82—H82 0.91 (2)
C4—H4 0.95 N82—H83 0.87 (2)
C5—C6 1.367 (3) N82—H84 0.89 (3)
C5—C10 1.416 (2) C9—C10 1.414 (2)
C5—H5 0.95 O1W—H1W 0.84 (3)
C6—C7 1.410 (2) O1W—H2W 0.76 (3)
C2—N1—C9 123.19 (15) C6—C7—H7 119.4
C2—N1—H1 117.0 (16) C7—C8—N81 126.43 (15)
C9—N1—H1 119.7 (16) C7—C8—C9 118.32 (14)
N1—C2—C3 120.21 (16) N81—C8—C9 115.20 (14)
N1—C2—H2 119.9 C8—N81—N82 115.00 (13)
C3—C2—H2 119.9 C8—N81—H81 111.7 (13)
C4—C3—C2 119.24 (16) N82—N81—H81 106.8 (13)
supporting information
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Acta Cryst. (2002). E58, o1070–o1071C2—C3—H3 120.4 N81—N82—H83 108.6 (13)
C3—C4—C10 120.66 (15) H82—N82—H83 116.2 (19)
C3—C4—H4 119.7 N81—N82—H84 107.1 (15)
C10—C4—H4 119.7 H82—N82—H84 108 (2)
C6—C5—C10 119.82 (15) H83—N82—H84 106 (2)
C6—C5—H5 120.1 N1—C9—C10 118.57 (15)
C10—C5—H5 120.1 N1—C9—C8 120.56 (14)
C5—C6—C7 121.10 (15) C10—C9—C8 120.87 (15)
C5—C6—H6 119.4 C4—C10—C9 118.04 (15)
C7—C6—H6 119.4 C4—C10—C5 123.25 (15)
C8—C7—C6 121.11 (16) C9—C10—C5 118.71 (15)
C8—C7—H7 119.4 H1W—O1W—H2W 104 (2)
C9—N1—C2—C3 0.6 (2) N81—C8—C9—N1 0.5 (2)
N1—C2—C3—C4 −2.9 (3) C7—C8—C9—C10 3.2 (2)
C2—C3—C4—C10 2.3 (2) N81—C8—C9—C10 −179.41 (13)
C10—C5—C6—C7 0.6 (2) C3—C4—C10—C9 0.5 (2)
C5—C6—C7—C8 0.1 (2) C3—C4—C10—C5 −179.92 (16)
C6—C7—C8—N81 −179.04 (15) N1—C9—C10—C4 −2.8 (2)
C6—C7—C8—C9 −1.9 (2) C8—C9—C10—C4 177.10 (14)
C7—C8—N81—N82 0.2 (2) N1—C9—C10—C5 177.62 (14)
C9—C8—N81—N82 −177.01 (13) C8—C9—C10—C5 −2.5 (2)
C2—N1—C9—C10 2.3 (2) C6—C5—C10—C4 −178.98 (15)
C2—N1—C9—C8 −177.57 (14) C6—C5—C10—C9 0.6 (2)
C7—C8—C9—N1 −176.98 (15)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N1—H1···O1Wi 0.78 (2) 2.05 (2) 2.817 (2) 165 (2)
N81—H81···Cl1ii 0.91 (2) 2.32 (2) 3.1983 (16) 164.5 (18)
N82—H82···Cl2ii 0.91 (2) 2.25 (2) 3.1476 (18) 169.8 (18)
N82—H83···O1Wiii 0.87 (2) 1.94 (2) 2.808 (2) 178.7 (19)
N82—H84···Cl2iv 0.89 (3) 2.39 (3) 3.1805 (17) 149.1 (19)
O1W—H1W···Cl1v 0.84 (3) 2.21 (3) 3.0348 (17) 164 (2)
O1W—H2W···Cl2iii 0.76 (3) 2.47 (3) 3.180 (2) 158 (2)