6-Amino-2-naphthoic acid monohydrate

The crystal structure of the title compound, C₁₁H₉NO₂·H₂O, consists of 6-amino-2-naphthoic acid mol­ecules, associated in dimers by O—H...O hydrogen bonds, and water mol­ecules. The water mol­ecules are hydrogen-bonded into chains which associate with the acid dimers, forming a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.141
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

6-Amino-2-naphthoic acid monohydrate

Crystal data

C11H9NO2·H2O	F(000) = 864
Mr = 205.21	Dx = 1.415 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1602 reflections
a = 22.582 (5) Å	θ = 3.2–26.3°
b = 12.222 (2) Å	µ = 0.10 mm^−1
c = 6.9793 (14) Å	T = 100 K
V = 1926.4 (7) Å^3	Block, colourless
Z = 8	0.22 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1837 independent reflections
Radiation source: fine-focus sealed tube	1372 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −24→27
Tmin = 0.966, Tmax = 0.980	k = −12→14
9442 measured reflections	l = −8→7

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0904P)^2] where P = (Fo^2 + 2Fc^2)/3
1837 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.38 e Å^−3
3 restraints	Δρmin = −0.22 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.58751 (8)	0.29824 (17)	0.7306 (3)	0.0342 (5)
H1A	0.5888 (11)	0.229 (2)	0.734 (3)	0.041*
H1B	0.5620 (11)	0.326 (2)	0.656 (3)	0.041*
C1	0.92323 (8)	0.44916 (15)	0.5761 (3)	0.0241 (5)
C2	0.86441 (8)	0.40688 (15)	0.6248 (3)	0.0228 (4)
C3	0.85808 (9)	0.30083 (15)	0.7069 (3)	0.0229 (5)
H3A	0.8923	0.2581	0.7332	0.027*
C4	0.80366 (8)	0.26059 (14)	0.7476 (3)	0.0225 (5)
H4A	0.8002	0.1906	0.8057	0.027*
C5	0.75152 (9)	0.32115 (14)	0.7049 (2)	0.0202 (4)
C6	0.69424 (8)	0.27889 (14)	0.7393 (3)	0.0231 (5)
H6A	0.6901	0.2083	0.7947	0.028*
C7	0.64451 (9)	0.33798 (16)	0.6941 (3)	0.0252 (5)
C8	0.65100 (9)	0.44362 (15)	0.6134 (3)	0.0245 (5)
H8A	0.6167	0.4852	0.5829	0.029*
C9	0.70563 (9)	0.48664 (15)	0.5790 (3)	0.0227 (4)
H9A	0.7089	0.5576	0.5246	0.027*
C10	0.75757 (8)	0.42702 (14)	0.6232 (3)	0.0210 (4)
C11	0.81502 (8)	0.46873 (14)	0.5868 (3)	0.0213 (4)
H11A	0.8194	0.5403	0.5356	0.026*
O1	0.96463 (6)	0.37675 (11)	0.5556 (2)	0.0315 (4)
H1	1.0023 (15)	0.406 (3)	0.526 (4)	0.082 (10)*
O2	0.93215 (6)	0.54971 (10)	0.5533 (2)	0.0323 (4)
O1W	0.49323 (9)	0.38859 (15)	0.4544 (3)	0.0605 (6)
H1W	0.4669 (13)	0.356 (3)	0.527 (4)	0.091*
H2AW	0.497 (3)	0.4591 (18)	0.441 (9)	0.091*	0.50
H2BW	0.505 (3)	0.350 (5)	0.350 (6)	0.091*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0242 (10)	0.0287 (9)	0.0497 (12)	−0.0006 (7)	−0.0045 (8)	0.0091 (9)
C1	0.0264 (11)	0.0211 (10)	0.0249 (10)	0.0006 (8)	−0.0050 (8)	0.0002 (8)
C2	0.0265 (11)	0.0217 (9)	0.0203 (9)	−0.0031 (8)	−0.0026 (8)	−0.0026 (8)
C3	0.0247 (11)	0.0206 (9)	0.0234 (10)	0.0020 (7)	−0.0034 (8)	−0.0013 (8)
C4	0.0313 (11)	0.0152 (9)	0.0209 (10)	0.0015 (8)	−0.0012 (8)	0.0008 (7)
C5	0.0276 (11)	0.0164 (9)	0.0166 (9)	−0.0007 (7)	−0.0002 (7)	−0.0024 (7)
C6	0.0302 (12)	0.0166 (9)	0.0226 (10)	−0.0034 (8)	−0.0004 (8)	0.0008 (7)
C7	0.0250 (11)	0.0257 (10)	0.0249 (10)	−0.0033 (8)	−0.0008 (8)	−0.0016 (8)
C8	0.0253 (11)	0.0235 (10)	0.0246 (10)	0.0029 (8)	−0.0026 (8)	−0.0013 (8)
C9	0.0311 (11)	0.0159 (9)	0.0212 (10)	0.0018 (7)	−0.0009 (8)	−0.0001 (7)
C10	0.0267 (11)	0.0173 (9)	0.0189 (9)	−0.0005 (7)	−0.0005 (8)	−0.0033 (8)
C11	0.0276 (11)	0.0153 (9)	0.0212 (10)	−0.0008 (7)	−0.0013 (8)	−0.0002 (7)
O1	0.0229 (8)	0.0282 (8)	0.0435 (9)	−0.0005 (6)	0.0006 (7)	0.0018 (6)
O2	0.0277 (8)	0.0232 (8)	0.0461 (9)	−0.0042 (6)	0.0004 (7)	0.0038 (6)
O1W	0.0468 (12)	0.0453 (11)	0.0892 (15)	−0.0093 (9)	−0.0179 (11)	0.0219 (11)

Geometric parameters (Å, º)

N1—C7	1.399 (3)	C6—C7	1.372 (3)
N1—H1A	0.85 (3)	C6—H6A	0.9500
N1—H1B	0.85 (2)	C7—C8	1.416 (3)
C1—O2	1.256 (2)	C8—C9	1.362 (3)
C1—O1	1.295 (2)	C8—H8A	0.9500
C1—C2	1.465 (3)	C9—C10	1.415 (3)
C2—C11	1.373 (3)	C9—H9A	0.9500
C2—C3	1.424 (3)	C10—C11	1.417 (3)
C3—C4	1.354 (3)	C11—H11A	0.9500
C3—H3A	0.9500	O1—H1	0.95 (3)
C4—C5	1.422 (3)	O1W—H1W	0.875 (18)
C4—H4A	0.9500	O1W—H2AW	0.87 (2)
C5—C6	1.413 (3)	O1W—H2BW	0.91 (2)
C5—C10	1.421 (3)
C7—N1—H1A	108.7 (17)	C5—C6—H6A	119.4
C7—N1—H1B	112.0 (17)	C6—C7—N1	121.89 (18)
H1A—N1—H1B	116 (2)	C6—C7—C8	119.12 (17)
O2—C1—O1	122.63 (17)	N1—C7—C8	118.96 (18)
O2—C1—C2	121.33 (17)	C9—C8—C7	121.04 (18)
O1—C1—C2	116.04 (16)	C9—C8—H8A	119.5
C11—C2—C3	119.82 (17)	C7—C8—H8A	119.5
C11—C2—C1	119.82 (17)	C8—C9—C10	120.89 (18)
C3—C2—C1	120.34 (17)	C8—C9—H9A	119.6
C4—C3—C2	120.40 (17)	C10—C9—H9A	119.6
C4—C3—H3A	119.8	C9—C10—C11	122.32 (17)
C2—C3—H3A	119.8	C9—C10—C5	118.49 (17)
C3—C4—C5	121.23 (17)	C11—C10—C5	119.19 (17)
C3—C4—H4A	119.4	C2—C11—C10	120.73 (17)
C5—C4—H4A	119.4	C2—C11—H11A	119.6
C6—C5—C10	119.27 (17)	C10—C11—H11A	119.6
C6—C5—C4	122.13 (16)	C1—O1—H1	114.5 (19)
C10—C5—C4	118.59 (17)	H1W—O1W—H2AW	126 (5)
C7—C6—C5	121.17 (17)	H1W—O1W—H2BW	115 (5)
C7—C6—H6A	119.4	H2AW—O1W—H2BW	113 (6)
O2—C1—C2—C11	21.0 (3)	C6—C7—C8—C9	0.5 (3)
O1—C1—C2—C11	−157.99 (17)	N1—C7—C8—C9	178.63 (18)
O2—C1—C2—C3	−160.60 (17)	C7—C8—C9—C10	−0.1 (3)
O1—C1—C2—C3	20.4 (3)	C8—C9—C10—C11	179.13 (17)
C11—C2—C3—C4	0.0 (3)	C8—C9—C10—C5	−0.2 (3)
C1—C2—C3—C4	−178.35 (17)	C6—C5—C10—C9	0.0 (3)
C2—C3—C4—C5	1.8 (3)	C4—C5—C10—C9	179.35 (15)
C3—C4—C5—C6	177.48 (16)	C6—C5—C10—C11	−179.29 (15)
C3—C4—C5—C10	−1.8 (3)	C4—C5—C10—C11	0.0 (3)
C10—C5—C6—C7	0.4 (3)	C3—C2—C11—C10	−1.8 (3)
C4—C5—C6—C7	−178.89 (16)	C1—C2—C11—C10	176.55 (16)
C5—C6—C7—N1	−178.72 (17)	C9—C10—C11—C2	−177.51 (17)
C5—C6—C7—C8	−0.7 (3)	C5—C10—C11—C2	1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.95 (3)	1.67 (3)	2.611 (2)	173 (3)
N1—H1A···O2^ii	0.85 (3)	2.57 (3)	3.310 (3)	146 (2)
N1—H1B···O1W	0.85 (2)	2.23 (3)	3.077 (3)	177 (2)
O1W—H1W···N1^iii	0.88 (2)	2.21 (2)	3.062 (3)	165 (3)
O1W—H2AW···O1W^iv	0.87 (2)	2.01 (3)	2.813 (4)	153 (6)
O1W—H2BW···O1W^v	0.91 (2)	2.17 (5)	2.870 (4)	133 (5)

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