The 1:1 proton-transfer monohydrate salt of 3,5-dinitro­salicylic acid with 1-amino-5-hydroxy­naphthalene

The title complex, 5-hydroxy­naphthalen-1-aminium 2-carb­oxy-4,6-dinitro­phenolate monohydrate, C₁₀H₁₀NO⁺·C₇H₃N₂O₇⁻·H₂O, shows a three-dimensional hydrogen-bonded framework structure in which columns comprising π-stacked cations and anions are inter­connected by conventional hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.066
• wR factor = 0.228
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N3     -   C3      ..       8.23 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: MSC/AFC Diffractmeter Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractmeter Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

5-hydroxynaphthalen-1-aminium 2-carboxy-4,6-dinitrophenolate monohydrate

Crystal data

C10H10NO^+·C7H3N2O7^−·H2O	F(000) = 840
Mr = 405.32	Dx = 1.583 Mg m^−3
Monoclinic, P21/n	Melting point = 467.8–469.5 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 27.324 (6) Å	Cell parameters from 22 reflections
b = 8.879 (4) Å	θ = 12.9–17.5°
c = 7.037 (4) Å	µ = 0.13 mm^−1
β = 94.98 (3)°	T = 297 K
V = 1700.8 (13) Å^3	Prismatic, dark brown
Z = 4	0.50 × 0.34 × 0.15 mm

Data collection

Rigaku AFC-7R diffractometer	2096 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω–2θ scans	h = −32→32
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999)	k = 0→10
Tmin = 0.938, Tmax = 0.981	l = −8→4
3545 measured reflections	3 standard reflections every 150 min
3006 independent reflections	intensity decay: 2.4%

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.228	H-atom parameters not refined
S = 1.14	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 2.1667P] where P = (Fo^2 + 2Fc^2)/3
3006 reflections	(Δ/σ)max = 0.002
262 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O5A	0.15967 (14)	−0.0536 (4)	0.0383 (6)	0.0529 (14)
N1A	0.06875 (16)	0.5404 (5)	0.2620 (7)	0.0456 (17)
C1A	0.07015 (18)	0.3815 (6)	0.2115 (7)	0.0374 (17)
C2A	0.02821 (19)	0.3000 (6)	0.2044 (8)	0.0418 (17)
C3A	0.02903 (19)	0.1453 (6)	0.1597 (8)	0.0425 (19)
C4A	0.07194 (19)	0.0796 (6)	0.1206 (8)	0.0407 (17)
C5A	0.16135 (19)	0.0954 (6)	0.0837 (8)	0.0406 (17)
C6A	0.20357 (19)	0.1797 (7)	0.0920 (8)	0.0457 (19)
C7A	0.2026 (2)	0.3316 (7)	0.1381 (8)	0.046 (2)
C8A	0.16008 (18)	0.4025 (6)	0.1773 (8)	0.0409 (17)
C9A	0.11612 (17)	0.3176 (6)	0.1692 (7)	0.0330 (17)
C10A	0.11611 (19)	0.1620 (6)	0.1241 (7)	0.0366 (17)
O2	0.13135 (17)	0.4621 (5)	0.6717 (7)	0.0703 (17)
O31	0.0379 (2)	0.4094 (6)	0.6891 (10)	0.103 (3)
O32	0.01000 (19)	0.1875 (7)	0.6763 (10)	0.099 (3)
O51	0.1036 (2)	−0.2159 (6)	0.4962 (8)	0.089 (2)
O52	0.1812 (2)	−0.2007 (6)	0.4740 (9)	0.096 (2)
O71	0.26305 (17)	0.2858 (6)	0.5687 (7)	0.079 (2)
O72	0.22299 (18)	0.4808 (6)	0.6577 (8)	0.0819 (19)
N3	0.0430 (2)	0.2804 (7)	0.6727 (8)	0.062 (2)
N5	0.1417 (2)	−0.1468 (6)	0.5095 (8)	0.0558 (19)
C1	0.1802 (2)	0.2464 (6)	0.6107 (7)	0.0404 (17)
C2	0.1351 (2)	0.3187 (6)	0.6427 (8)	0.0449 (19)
C3	0.0935 (2)	0.2234 (7)	0.6393 (8)	0.0428 (19)
C4	0.09518 (18)	0.0745 (6)	0.5995 (7)	0.0393 (17)
C5	0.1392 (2)	0.0109 (5)	0.5632 (7)	0.0373 (17)
C6	0.18198 (18)	0.0953 (7)	0.5688 (7)	0.0406 (19)
C7	0.2268 (2)	0.3370 (8)	0.6105 (9)	0.054 (3)
O1W	0.09512 (16)	0.6862 (5)	0.9408 (7)	0.0678 (17)
H2A	−0.00180	0.34700	0.22950	0.0500*
H3A	−0.00030	0.08730	0.15680	0.0510*
H4A	0.07220	−0.02470	0.09020	0.0490*
H5A	0.18600	−0.10800	0.00200	0.0640*
H6A	0.23370	0.13380	0.06610	0.0550*
H7A	0.23220	0.38790	0.14260	0.0560*
H8A	0.16010	0.50650	0.20920	0.0490*
H11A	0.08790	0.58630	0.36030	0.0580*
H12A	0.07700	0.58000	0.15400	0.0580*
H13A	0.03750	0.56570	0.29490	0.0580*
H4	0.06630	0.01480	0.59670	0.0480*
H6	0.21220	0.04920	0.54400	0.0490*
H72	0.19000	0.48500	0.66300	0.0980*
H11W	0.12000	0.73510	0.96080	0.0820*
H12W	0.10400	0.61600	0.85700	0.0820*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5A	0.044 (2)	0.045 (2)	0.071 (3)	0.0106 (19)	0.012 (2)	−0.006 (2)
N1A	0.038 (3)	0.041 (3)	0.059 (3)	−0.001 (2)	0.011 (2)	−0.015 (2)
C1A	0.037 (3)	0.037 (3)	0.038 (3)	0.003 (2)	0.003 (2)	−0.001 (2)
C2A	0.033 (3)	0.043 (3)	0.049 (3)	0.002 (3)	0.001 (2)	−0.002 (3)
C3A	0.031 (3)	0.042 (3)	0.054 (4)	−0.003 (2)	0.001 (3)	−0.005 (3)
C4A	0.040 (3)	0.037 (3)	0.044 (3)	−0.006 (2)	−0.002 (2)	−0.004 (3)
C5A	0.036 (3)	0.046 (3)	0.040 (3)	0.006 (3)	0.005 (2)	−0.003 (3)
C6A	0.036 (3)	0.060 (4)	0.042 (3)	0.010 (3)	0.009 (3)	−0.001 (3)
C7A	0.034 (3)	0.055 (4)	0.050 (4)	−0.005 (3)	0.008 (3)	0.004 (3)
C8A	0.034 (3)	0.044 (3)	0.044 (3)	−0.002 (2)	0.000 (2)	0.001 (3)
C9A	0.029 (3)	0.045 (3)	0.025 (3)	−0.001 (2)	0.003 (2)	0.001 (2)
C10A	0.040 (3)	0.040 (3)	0.030 (3)	0.005 (2)	0.005 (2)	0.000 (2)
O2	0.081 (3)	0.046 (3)	0.086 (3)	−0.004 (2)	0.020 (3)	−0.008 (2)
O31	0.091 (4)	0.065 (4)	0.154 (6)	0.019 (3)	0.019 (4)	−0.031 (4)
O32	0.049 (3)	0.099 (4)	0.152 (6)	−0.001 (3)	0.031 (3)	0.004 (4)
O51	0.097 (4)	0.055 (3)	0.112 (5)	−0.022 (3)	−0.004 (3)	−0.015 (3)
O52	0.104 (4)	0.054 (3)	0.132 (5)	0.028 (3)	0.029 (4)	−0.011 (3)
O71	0.039 (3)	0.107 (4)	0.092 (4)	−0.010 (3)	0.007 (3)	0.028 (3)
O72	0.071 (3)	0.071 (3)	0.104 (4)	−0.034 (3)	0.010 (3)	−0.017 (3)
N3	0.069 (4)	0.064 (4)	0.053 (3)	−0.003 (3)	0.000 (3)	0.001 (3)
N5	0.072 (4)	0.038 (3)	0.056 (3)	−0.005 (3)	−0.003 (3)	−0.001 (2)
C1	0.041 (3)	0.044 (3)	0.035 (3)	−0.019 (3)	−0.003 (2)	0.007 (3)
C2	0.068 (4)	0.029 (3)	0.037 (3)	0.001 (3)	0.001 (3)	−0.003 (2)
C3	0.040 (3)	0.053 (4)	0.036 (3)	0.016 (3)	0.006 (2)	0.006 (3)
C4	0.033 (3)	0.048 (3)	0.037 (3)	−0.007 (3)	0.004 (2)	0.006 (3)
C5	0.050 (3)	0.022 (3)	0.039 (3)	0.000 (2)	−0.001 (2)	0.000 (2)
C6	0.029 (3)	0.057 (4)	0.036 (3)	0.008 (3)	0.004 (2)	0.007 (3)
C7	0.045 (4)	0.069 (5)	0.045 (4)	−0.013 (3)	−0.004 (3)	0.009 (3)
O1W	0.065 (3)	0.058 (3)	0.082 (3)	−0.005 (2)	0.015 (2)	−0.004 (3)

Geometric parameters (Å, º)

O5A—C5A	1.361 (6)	C4A—C10A	1.410 (7)
O5A—H5A	0.9200	C5A—C6A	1.372 (8)
O2—C2	1.295 (7)	C5A—C10A	1.421 (7)
O31—N3	1.161 (8)	C6A—C7A	1.388 (9)
O32—N3	1.224 (8)	C7A—C8A	1.370 (8)
O51—N5	1.205 (8)	C8A—C9A	1.415 (7)
O52—N5	1.226 (8)	C9A—C10A	1.418 (8)
O71—C7	1.151 (8)	C2A—H2A	0.9500
O72—C7	1.326 (9)	C3A—H3A	0.9500
O72—H72	0.9100	C4A—H4A	0.9500
O1W—H12W	0.9100	C6A—H6A	0.9500
O1W—H11W	0.8100	C7A—H7A	0.9500
N1A—C1A	1.456 (7)	C8A—H8A	0.9500
N1A—H13A	0.9300	C1—C7	1.506 (8)
N1A—H12A	0.8800	C1—C6	1.375 (8)
N1A—H11A	0.9200	C1—C2	1.425 (8)
N3—C3	1.507 (8)	C2—C3	1.416 (8)
N5—C5	1.454 (7)	C3—C4	1.353 (8)
C1A—C9A	1.433 (7)	C4—C5	1.373 (7)
C1A—C2A	1.353 (7)	C5—C6	1.386 (7)
C2A—C3A	1.410 (8)	C4—H4	0.9500
C3A—C4A	1.359 (7)	C6—H6	0.9500
C5A—O5A—H5A	124.00	C1A—C2A—H2A	120.00
C7—O72—H72	99.00	C3A—C2A—H2A	120.00
H11W—O1W—H12W	102.00	C4A—C3A—H3A	120.00
H11A—N1A—H13A	100.00	C2A—C3A—H3A	120.00
C1A—N1A—H11A	126.00	C10A—C4A—H4A	119.00
C1A—N1A—H12A	99.00	C3A—C4A—H4A	119.00
C1A—N1A—H13A	110.00	C7A—C6A—H6A	120.00
H11A—N1A—H12A	107.00	C5A—C6A—H6A	120.00
H12A—N1A—H13A	115.00	C6A—C7A—H7A	119.00
O31—N3—C3	117.8 (6)	C8A—C7A—H7A	119.00
O32—N3—C3	117.6 (6)	C7A—C8A—H8A	121.00
O31—N3—O32	124.6 (6)	C9A—C8A—H8A	121.00
O51—N5—C5	116.8 (5)	C2—C1—C7	120.2 (5)
O52—N5—C5	119.4 (5)	C6—C1—C7	118.4 (5)
O51—N5—O52	123.7 (6)	C2—C1—C6	121.4 (5)
N1A—C1A—C9A	118.5 (4)	C1—C2—C3	115.6 (5)
C2A—C1A—C9A	122.4 (5)	O2—C2—C3	121.1 (5)
N1A—C1A—C2A	119.2 (5)	O2—C2—C1	123.3 (5)
C1A—C2A—C3A	120.0 (5)	N3—C3—C2	122.8 (5)
C2A—C3A—C4A	119.6 (5)	C2—C3—C4	123.1 (5)
C3A—C4A—C10A	121.7 (5)	N3—C3—C4	114.1 (5)
C6A—C5A—C10A	120.5 (5)	C3—C4—C5	119.1 (5)
O5A—C5A—C6A	123.5 (5)	N5—C5—C6	118.0 (5)
O5A—C5A—C10A	116.1 (5)	N5—C5—C4	120.4 (5)
C5A—C6A—C7A	120.5 (5)	C4—C5—C6	121.5 (5)
C6A—C7A—C8A	121.8 (5)	C1—C6—C5	119.2 (5)
C7A—C8A—C9A	118.6 (5)	O72—C7—C1	115.4 (5)
C8A—C9A—C10A	120.8 (5)	O71—C7—O72	122.2 (6)
C1A—C9A—C10A	116.7 (4)	O71—C7—C1	122.4 (6)
C1A—C9A—C8A	122.5 (5)	C3—C4—H4	120.00
C4A—C10A—C9A	119.6 (5)	C5—C4—H4	120.00
C5A—C10A—C9A	117.8 (5)	C1—C6—H6	120.00
C4A—C10A—C5A	122.6 (5)	C5—C6—H6	120.00
O32—N3—C3—C2	−176.4 (6)	C7A—C8A—C9A—C10A	0.9 (8)
O32—N3—C3—C4	5.8 (8)	C7A—C8A—C9A—C1A	178.8 (5)
O31—N3—C3—C2	5.2 (9)	C8A—C9A—C10A—C5A	−1.3 (7)
O31—N3—C3—C4	−172.6 (6)	C1A—C9A—C10A—C4A	0.8 (7)
O51—N5—C5—C4	1.1 (8)	C8A—C9A—C10A—C4A	178.8 (5)
O52—N5—C5—C6	1.1 (8)	C1A—C9A—C10A—C5A	−179.3 (5)
O51—N5—C5—C6	−176.3 (5)	C6—C1—C2—C3	3.5 (8)
O52—N5—C5—C4	178.6 (6)	C6—C1—C2—O2	−175.9 (5)
N1A—C1A—C2A—C3A	−178.7 (5)	C2—C1—C6—C5	−1.9 (8)
C2A—C1A—C9A—C10A	−1.7 (7)	C7—C1—C2—O2	0.4 (8)
N1A—C1A—C9A—C8A	0.9 (7)	C7—C1—C2—C3	179.8 (5)
C2A—C1A—C9A—C8A	−179.7 (5)	C2—C1—C7—O72	5.6 (8)
C9A—C1A—C2A—C3A	2.0 (8)	C6—C1—C7—O71	3.4 (9)
N1A—C1A—C9A—C10A	178.9 (4)	C6—C1—C7—O72	−178.0 (5)
C1A—C2A—C3A—C4A	−1.2 (8)	C7—C1—C6—C5	−178.3 (5)
C2A—C3A—C4A—C10A	0.3 (8)	C2—C1—C7—O71	−173.0 (6)
C3A—C4A—C10A—C9A	−0.1 (8)	C1—C2—C3—N3	179.3 (5)
C3A—C4A—C10A—C5A	180.0 (5)	O2—C2—C3—N3	−1.3 (9)
C10A—C5A—C6A—C7A	−0.7 (8)	O2—C2—C3—C4	176.4 (5)
O5A—C5A—C6A—C7A	179.6 (5)	C1—C2—C3—C4	−3.1 (8)
C6A—C5A—C10A—C9A	1.2 (8)	C2—C3—C4—C5	1.0 (8)
C6A—C5A—C10A—C4A	−178.9 (5)	N3—C3—C4—C5	178.9 (5)
O5A—C5A—C10A—C4A	0.9 (8)	C3—C4—C5—N5	−176.5 (5)
O5A—C5A—C10A—C9A	−179.1 (5)	C3—C4—C5—C6	0.8 (8)
C5A—C6A—C7A—C8A	0.2 (9)	C4—C5—C6—C1	−0.4 (8)
C6A—C7A—C8A—C9A	−0.3 (8)	N5—C5—C6—C1	177.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O72—H72···O2	0.91	1.62	2.520 (7)	170
O5A—H5A···O71^i	0.92	1.79	2.708 (6)	180
O1W—H11W···O5A^ii	0.81	2.21	2.951 (6)	152
O1W—H12W···O2	0.91	2.07	2.975 (7)	174
N1A—H11A···O51^iii	0.92	2.03	2.834 (7)	145
N1A—H12A···O1W^iv	0.88	1.87	2.754 (7)	173
N1A—H13A···O31^v	0.93	2.0800	2.997 (7)	166
N1A—H13A···O32^v	0.93	2.56	3.289 (8)	135
C2A—H2A···O31^v	0.95	2.47	3.274 (8)	143
C6A—H6A···O72^i	0.95	2.46	3.293 (8)	146

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