organic compounds
The crystal structure of the title compound, C11H9NO2·H2O, consists of 6-amino-2-naphthoic acid molecules, associated in dimers by O—HO hydrogen bonds, and water molecules. The water molecules are hydrogen-bonded into chains which associate with the acid dimers, forming a three-dimensional framework.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000116/bh2066sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000116/bh2066Isup2.hkl |
CCDC reference: 636131
Computing details top
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 top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.22 × 0.20 × 0.20 mm |
Data collection top
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 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0904P)2] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.95 (3) | 1.67 (3) | 2.611 (2) | 173 (3) |
N1—H1A···O2ii | 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···N1iii | 0.88 (2) | 2.21 (2) | 3.062 (3) | 165 (3) |
O1W—H2AW···O1Wiv | 0.87 (2) | 2.01 (3) | 2.813 (4) | 153 (6) |
O1W—H2BW···O1Wv | 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. |