Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012612/wn6038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012612/wn6038Isup2.hkl |
CCDC reference: 170941
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 15.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Nitrilotriacetic acid and 1,10-phenanthroline were obtained from Aldrich. The title complex was prepared by slow evaporatioin of an acid–base (1:1) solution in N,N-dimethylformamide (DMF) at room temperature.
All H atoms not bonded to carbon were located from difference Fourier maps and were refined with isotropic displacement parameters. H100 was refined without restraint. H1 and H2 were refined with the N—H distances restrained to be equivalent with an s.u. of 0.01 Å. H101 and H102, associated with the water molecule, were refined with the O—H distances restrained to be equivalent with an s.u. of 0.01 Å, and the H101···H102 distance was restrained to be 1.633 times the value of the O—H distance, with an s.u. of 0.02 Å; these restraints ensure a reasonable geometry for the water molecule. All H atoms bonded to C atoms were placed geometrically and refined using a riding model with the Uiso values for each H atom taken as 1.2 Ueq of the carrier atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.
C6H8NO6·C12H9N2·H2O | Dx = 1.441 Mg m−3 |
Mr = 389.36 | Melting point: not measured K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
a = 22.7045 (6) Å | Cell parameters from 22808 reflections |
b = 11.1044 (3) Å | θ = 1.0–27.5° |
c = 14.2366 (2) Å | µ = 0.11 mm−1 |
V = 3589.33 (14) Å3 | T = 180 K |
Z = 8 | Block, colourless |
F(000) = 1632 | 0.46 × 0.46 × 0.30 mm |
Nonius KappaCCD diffractometer | 4114 independent reflections |
Radiation source: fine-focus sealed tube | 3414 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
thin–slice ω and ϕ scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −21→29 |
Tmin = 0.932, Tmax = 0.967 | k = −11→14 |
22344 measured reflections | l = −18→18 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0466P)2 + 1.3895P] where P = (Fo2 + 2Fc2)/3 |
4114 reflections | (Δ/σ)max = 0.013 |
275 parameters | Δρmax = 0.39 e Å−3 |
5 restraints | Δρmin = −0.26 e Å−3 |
C6H8NO6·C12H9N2·H2O | V = 3589.33 (14) Å3 |
Mr = 389.36 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 22.7045 (6) Å | µ = 0.11 mm−1 |
b = 11.1044 (3) Å | T = 180 K |
c = 14.2366 (2) Å | 0.46 × 0.46 × 0.30 mm |
Nonius KappaCCD diffractometer | 4114 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3414 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.967 | Rint = 0.038 |
22344 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 5 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.39 e Å−3 |
4114 reflections | Δρmin = −0.26 e Å−3 |
275 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.68405 (4) | 0.35751 (10) | 0.17166 (7) | 0.0340 (2) | |
O2 | 0.76622 (4) | 0.32979 (9) | 0.08694 (6) | 0.0283 (2) | |
O3 | 0.71315 (4) | 0.30620 (8) | 0.39570 (6) | 0.0280 (2) | |
O4 | 0.76944 (5) | 0.36248 (9) | 0.51723 (6) | 0.0299 (2) | |
H100 | 0.7565 (10) | 0.283 (2) | 0.5426 (14) | 0.065 (6)* | |
O5 | 0.62768 (5) | 0.56998 (9) | 0.35713 (8) | 0.0351 (3) | |
O6 | 0.64027 (4) | 0.76469 (9) | 0.31835 (8) | 0.0336 (2) | |
N1 | 0.73304 (5) | 0.50254 (9) | 0.29515 (7) | 0.0187 (2) | |
H1 | 0.6992 (7) | 0.4529 (15) | 0.2951 (12) | 0.040 (5)* | |
N2 | 0.47064 (5) | 0.82797 (11) | 0.13801 (8) | 0.0254 (2) | |
H2 | 0.4298 (7) | 0.8316 (17) | 0.1537 (13) | 0.049 (5)* | |
N3 | 0.42069 (5) | 1.05270 (11) | 0.16445 (8) | 0.0271 (3) | |
C1 | 0.77282 (5) | 0.44984 (11) | 0.22214 (8) | 0.0209 (3) | |
H1A | 0.8032 | 0.3993 | 0.2526 | 0.025* | |
H1B | 0.7929 | 0.5152 | 0.1874 | 0.025* | |
C2 | 0.73673 (6) | 0.37369 (12) | 0.15421 (8) | 0.0219 (3) | |
C3 | 0.75899 (6) | 0.49919 (12) | 0.39187 (8) | 0.0230 (3) | |
H3A | 0.7422 | 0.5647 | 0.4307 | 0.028* | |
H3B | 0.8022 | 0.5106 | 0.3885 | 0.028* | |
C4 | 0.74486 (6) | 0.37797 (11) | 0.43542 (8) | 0.0212 (3) | |
C5 | 0.71133 (6) | 0.62433 (11) | 0.26760 (9) | 0.0223 (3) | |
H5A | 0.7039 | 0.6261 | 0.1991 | 0.027* | |
H5B | 0.7419 | 0.6852 | 0.2820 | 0.027* | |
C6 | 0.65459 (6) | 0.65571 (12) | 0.32009 (9) | 0.0250 (3) | |
C7 | 0.49264 (7) | 0.71759 (13) | 0.12856 (10) | 0.0307 (3) | |
H7 | 0.4679 | 0.6498 | 0.1384 | 0.037* | |
C8 | 0.55140 (7) | 0.70006 (14) | 0.10448 (11) | 0.0351 (3) | |
H8 | 0.5672 | 0.6211 | 0.0992 | 0.042* | |
C9 | 0.58612 (6) | 0.79899 (14) | 0.08853 (10) | 0.0324 (3) | |
H9 | 0.6263 | 0.7884 | 0.0716 | 0.039* | |
C10 | 0.56293 (6) | 0.91605 (13) | 0.09691 (9) | 0.0261 (3) | |
C11 | 0.59705 (6) | 1.02138 (14) | 0.07812 (9) | 0.0295 (3) | |
H11 | 0.6369 | 1.0134 | 0.0585 | 0.035* | |
C12 | 0.57330 (6) | 1.13219 (14) | 0.08793 (10) | 0.0303 (3) | |
H12 | 0.5967 | 1.2011 | 0.0751 | 0.036* | |
C13 | 0.51324 (6) | 1.14768 (13) | 0.11745 (9) | 0.0270 (3) | |
C14 | 0.48717 (7) | 1.26186 (14) | 0.12946 (10) | 0.0331 (3) | |
H14 | 0.5091 | 1.3330 | 0.1172 | 0.040* | |
C15 | 0.42995 (7) | 1.26917 (14) | 0.15894 (11) | 0.0345 (3) | |
H15 | 0.4116 | 1.3453 | 0.1678 | 0.041* | |
C16 | 0.39880 (6) | 1.16227 (13) | 0.17589 (10) | 0.0312 (3) | |
H16 | 0.3592 | 1.1689 | 0.1970 | 0.037* | |
C17 | 0.47769 (6) | 1.04597 (13) | 0.13567 (9) | 0.0241 (3) | |
C18 | 0.50349 (6) | 0.92899 (12) | 0.12381 (8) | 0.0231 (3) | |
O100 | 0.59649 (6) | 0.44024 (12) | 0.04777 (9) | 0.0489 (3) | |
H101 | 0.6313 (9) | 0.425 (2) | 0.0823 (16) | 0.096 (9)* | |
H102 | 0.6095 (11) | 0.444 (3) | −0.0154 (14) | 0.103 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0269 (5) | 0.0451 (6) | 0.0298 (5) | −0.0066 (4) | −0.0002 (4) | −0.0102 (4) |
O2 | 0.0347 (5) | 0.0264 (5) | 0.0239 (5) | −0.0019 (4) | 0.0046 (4) | −0.0074 (4) |
O3 | 0.0353 (5) | 0.0234 (5) | 0.0254 (5) | −0.0092 (4) | −0.0059 (4) | 0.0028 (4) |
O4 | 0.0419 (6) | 0.0261 (5) | 0.0216 (5) | −0.0089 (4) | −0.0097 (4) | 0.0061 (4) |
O5 | 0.0344 (5) | 0.0252 (5) | 0.0457 (6) | −0.0014 (4) | 0.0144 (5) | 0.0040 (4) |
O6 | 0.0285 (5) | 0.0215 (5) | 0.0508 (6) | 0.0038 (4) | 0.0115 (4) | 0.0016 (4) |
N1 | 0.0239 (5) | 0.0155 (5) | 0.0166 (5) | −0.0010 (4) | −0.0001 (4) | −0.0002 (4) |
N2 | 0.0219 (5) | 0.0293 (6) | 0.0250 (5) | −0.0008 (5) | −0.0006 (4) | −0.0001 (5) |
N3 | 0.0223 (5) | 0.0310 (6) | 0.0279 (6) | 0.0004 (5) | −0.0010 (4) | −0.0006 (5) |
C1 | 0.0223 (6) | 0.0197 (6) | 0.0208 (6) | 0.0016 (5) | 0.0008 (5) | −0.0022 (5) |
C2 | 0.0274 (6) | 0.0196 (6) | 0.0185 (6) | 0.0009 (5) | −0.0019 (5) | 0.0000 (5) |
C3 | 0.0326 (7) | 0.0203 (6) | 0.0160 (6) | −0.0047 (5) | −0.0037 (5) | −0.0002 (5) |
C4 | 0.0247 (6) | 0.0204 (6) | 0.0186 (6) | −0.0015 (5) | 0.0003 (5) | 0.0010 (5) |
C5 | 0.0274 (6) | 0.0164 (6) | 0.0232 (6) | 0.0024 (5) | 0.0022 (5) | 0.0030 (5) |
C6 | 0.0263 (6) | 0.0224 (7) | 0.0264 (6) | −0.0004 (5) | 0.0029 (5) | −0.0002 (5) |
C7 | 0.0310 (7) | 0.0279 (7) | 0.0334 (7) | −0.0010 (6) | −0.0023 (6) | −0.0006 (6) |
C8 | 0.0314 (8) | 0.0347 (8) | 0.0390 (8) | 0.0054 (6) | −0.0010 (6) | −0.0049 (6) |
C9 | 0.0230 (7) | 0.0426 (9) | 0.0317 (7) | 0.0037 (6) | −0.0010 (5) | −0.0046 (6) |
C10 | 0.0218 (6) | 0.0356 (8) | 0.0209 (6) | −0.0001 (5) | −0.0024 (5) | −0.0015 (5) |
C11 | 0.0207 (6) | 0.0435 (9) | 0.0244 (6) | −0.0047 (6) | −0.0009 (5) | 0.0006 (6) |
C12 | 0.0267 (7) | 0.0369 (8) | 0.0273 (7) | −0.0090 (6) | −0.0018 (5) | 0.0044 (6) |
C13 | 0.0271 (7) | 0.0317 (8) | 0.0221 (6) | −0.0036 (6) | −0.0044 (5) | 0.0024 (5) |
C14 | 0.0348 (8) | 0.0297 (8) | 0.0348 (8) | −0.0053 (6) | −0.0052 (6) | 0.0034 (6) |
C15 | 0.0350 (8) | 0.0291 (8) | 0.0395 (8) | 0.0043 (6) | −0.0063 (6) | 0.0003 (6) |
C16 | 0.0248 (7) | 0.0348 (8) | 0.0340 (7) | 0.0029 (6) | −0.0033 (6) | −0.0018 (6) |
C17 | 0.0222 (6) | 0.0308 (7) | 0.0194 (6) | −0.0015 (5) | −0.0034 (5) | 0.0007 (5) |
C18 | 0.0216 (6) | 0.0290 (7) | 0.0187 (6) | −0.0024 (5) | −0.0027 (5) | 0.0001 (5) |
O100 | 0.0501 (7) | 0.0527 (8) | 0.0438 (7) | 0.0170 (6) | 0.0038 (6) | 0.0029 (6) |
O1—C2 | 1.2348 (16) | C5—H5B | 0.9900 |
O2—C2 | 1.2661 (15) | C7—C8 | 1.391 (2) |
O3—C4 | 1.2137 (15) | C7—H7 | 0.9500 |
O4—C4 | 1.3029 (15) | C8—C9 | 1.371 (2) |
O4—H100 | 1.00 (2) | C8—H8 | 0.9500 |
O5—C6 | 1.2480 (16) | C9—C10 | 1.408 (2) |
O6—C6 | 1.2532 (16) | C9—H9 | 0.9500 |
N1—C5 | 1.4920 (16) | C10—C18 | 1.4103 (18) |
N1—C1 | 1.4962 (15) | C10—C11 | 1.428 (2) |
N1—C3 | 1.4981 (15) | C11—C12 | 1.351 (2) |
N1—H1 | 0.946 (15) | C11—H11 | 0.9500 |
N2—C7 | 1.3303 (18) | C12—C13 | 1.437 (2) |
N2—C18 | 1.3621 (17) | C12—H12 | 0.9500 |
N2—H2 | 0.954 (15) | C13—C14 | 1.410 (2) |
N3—C16 | 1.3243 (18) | C13—C17 | 1.4122 (19) |
N3—C17 | 1.3593 (17) | C14—C15 | 1.368 (2) |
C1—C2 | 1.5237 (17) | C14—H14 | 0.9500 |
C1—H1A | 0.9900 | C15—C16 | 1.403 (2) |
C1—H1B | 0.9900 | C15—H15 | 0.9500 |
C3—C4 | 1.5164 (18) | C16—H16 | 0.9500 |
C3—H3A | 0.9900 | C17—C18 | 1.4350 (19) |
C3—H3B | 0.9900 | O100—H101 | 0.95 (2) |
C5—C6 | 1.5295 (18) | O100—H102 | 0.95 (2) |
C5—H5A | 0.9900 | ||
C4—O4—H100 | 108.3 (12) | N2—C7—C8 | 120.92 (14) |
C5—N1—C1 | 111.80 (9) | N2—C7—H7 | 119.5 |
C5—N1—C3 | 113.21 (10) | C8—C7—H7 | 119.5 |
C1—N1—C3 | 113.05 (10) | C9—C8—C7 | 118.70 (14) |
C5—N1—H1 | 105.0 (11) | C9—C8—H8 | 120.7 |
C1—N1—H1 | 105.2 (10) | C7—C8—H8 | 120.7 |
C3—N1—H1 | 107.8 (10) | C8—C9—C10 | 120.72 (13) |
C7—N2—C18 | 122.56 (12) | C8—C9—H9 | 119.6 |
C7—N2—H2 | 115.3 (11) | C10—C9—H9 | 119.6 |
C18—N2—H2 | 122.1 (11) | C9—C10—C18 | 118.36 (13) |
C16—N3—C17 | 116.42 (12) | C9—C10—C11 | 122.52 (13) |
N1—C1—C2 | 109.47 (10) | C18—C10—C11 | 119.11 (13) |
N1—C1—H1A | 109.8 | C12—C11—C10 | 120.67 (13) |
C2—C1—H1A | 109.8 | C12—C11—H11 | 119.7 |
N1—C1—H1B | 109.8 | C10—C11—H11 | 119.7 |
C2—C1—H1B | 109.8 | C11—C12—C13 | 121.20 (13) |
H1A—C1—H1B | 108.2 | C11—C12—H12 | 119.4 |
O1—C2—O2 | 127.47 (12) | C13—C12—H12 | 119.4 |
O1—C2—C1 | 118.30 (11) | C14—C13—C17 | 117.19 (13) |
O2—C2—C1 | 114.16 (11) | C14—C13—C12 | 122.79 (13) |
N1—C3—C4 | 108.33 (10) | C17—C13—C12 | 120.02 (13) |
N1—C3—H3A | 110.0 | C15—C14—C13 | 119.31 (14) |
C4—C3—H3A | 110.0 | C15—C14—H14 | 120.3 |
N1—C3—H3B | 110.0 | C13—C14—H14 | 120.3 |
C4—C3—H3B | 110.0 | C14—C15—C16 | 118.78 (14) |
H3A—C3—H3B | 108.4 | C14—C15—H15 | 120.6 |
O3—C4—O4 | 125.72 (12) | C16—C15—H15 | 120.6 |
O3—C4—C3 | 121.19 (11) | N3—C16—C15 | 124.54 (13) |
O4—C4—C3 | 113.08 (11) | N3—C16—H16 | 117.7 |
N1—C5—C6 | 110.88 (10) | C15—C16—H16 | 117.7 |
N1—C5—H5A | 109.5 | N3—C17—C13 | 123.74 (13) |
C6—C5—H5A | 109.5 | N3—C17—C18 | 118.29 (12) |
N1—C5—H5B | 109.5 | C13—C17—C18 | 117.97 (12) |
C6—C5—H5B | 109.5 | N2—C18—C10 | 118.71 (12) |
H5A—C5—H5B | 108.1 | N2—C18—C17 | 120.30 (12) |
O5—C6—O6 | 128.17 (13) | C10—C18—C17 | 120.99 (12) |
O5—C6—C5 | 116.42 (11) | H101—O100—H102 | 103.9 (17) |
O6—C6—C5 | 115.39 (11) | ||
C5—N1—C1—C2 | −92.27 (12) | C17—C13—C14—C15 | 0.9 (2) |
C3—N1—C1—C2 | 138.58 (11) | C12—C13—C14—C15 | −179.15 (13) |
N1—C1—C2—O1 | −6.00 (16) | C13—C14—C15—C16 | −0.3 (2) |
N1—C1—C2—O2 | 176.76 (10) | C17—N3—C16—C15 | 1.1 (2) |
C5—N1—C3—C4 | 145.42 (11) | C14—C15—C16—N3 | −0.7 (2) |
C1—N1—C3—C4 | −86.16 (12) | C16—N3—C17—C13 | −0.43 (19) |
N1—C3—C4—O3 | −5.62 (17) | C16—N3—C17—C18 | 179.03 (12) |
N1—C3—C4—O4 | 175.05 (10) | C14—C13—C17—N3 | −0.54 (19) |
C1—N1—C5—C6 | 158.04 (10) | C12—C13—C17—N3 | 179.51 (12) |
C3—N1—C5—C6 | −72.89 (13) | C14—C13—C17—C18 | 180.00 (12) |
N1—C5—C6—O5 | −17.20 (17) | C12—C13—C17—C18 | 0.04 (18) |
N1—C5—C6—O6 | 164.49 (11) | C7—N2—C18—C10 | 0.79 (19) |
C18—N2—C7—C8 | 0.8 (2) | C7—N2—C18—C17 | −179.51 (12) |
N2—C7—C8—C9 | −1.4 (2) | C9—C10—C18—N2 | −1.77 (18) |
C7—C8—C9—C10 | 0.4 (2) | C11—C10—C18—N2 | 177.46 (11) |
C8—C9—C10—C18 | 1.2 (2) | C9—C10—C18—C17 | 178.55 (12) |
C8—C9—C10—C11 | −178.02 (13) | C11—C10—C18—C17 | −2.23 (18) |
C9—C10—C11—C12 | −179.31 (13) | N3—C17—C18—N2 | 2.28 (18) |
C18—C10—C11—C12 | 1.50 (19) | C13—C17—C18—N2 | −178.22 (11) |
C10—C11—C12—C13 | 0.0 (2) | N3—C17—C18—C10 | −178.03 (11) |
C11—C12—C13—C14 | 179.27 (13) | C13—C17—C18—C10 | 1.46 (18) |
C11—C12—C13—C17 | −0.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H100···O2i | 1.00 (2) | 1.49 (2) | 2.4897 (13) | 175 (2) |
N1—H1···O1 | 0.95 (2) | 2.08 (2) | 2.6310 (14) | 116 (1) |
N2—H2···O6ii | 0.95 (2) | 1.80 (2) | 2.6874 (15) | 153 (2) |
O100—H101···O1 | 0.95 (2) | 1.90 (2) | 2.8119 (17) | 161 (2) |
O100—H102···O5iii | 0.95 (2) | 1.87 (2) | 2.8072 (16) | 171 (3) |
Symmetry codes: (i) −x+3/2, −y+1/2, z+1/2; (ii) −x+1, y, −z+1/2; (iii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H8NO6·C12H9N2·H2O |
Mr | 389.36 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 180 |
a, b, c (Å) | 22.7045 (6), 11.1044 (3), 14.2366 (2) |
V (Å3) | 3589.33 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.46 × 0.46 × 0.30 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.932, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22344, 4114, 3414 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.102, 1.03 |
No. of reflections | 4114 |
No. of parameters | 275 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.26 |
Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H100···O2i | 1.00 (2) | 1.49 (2) | 2.4897 (13) | 175 (2) |
N1—H1···O1 | 0.946 (15) | 2.080 (16) | 2.6310 (14) | 115.6 (13) |
N2—H2···O6ii | 0.954 (15) | 1.801 (16) | 2.6874 (15) | 153.2 (17) |
O100—H101···O1 | 0.95 (2) | 1.90 (2) | 2.8119 (17) | 161 (2) |
O100—H102···O5iii | 0.95 (2) | 1.87 (2) | 2.8072 (16) | 171 (3) |
Symmetry codes: (i) −x+3/2, −y+1/2, z+1/2; (ii) −x+1, y, −z+1/2; (iii) x, −y+1, z−1/2. |
With a view towards the prediction of solid-state organic crystal structures, we are currently studying the supramolecular structures of cocrystals containing organic acids and organic bases. Nitrilotriacetic acid (NTA), which posesses three carboxylic acid groups, is commonly found as a multidentate ligand in many metal–chelate compounds (Kaneyoshi et al., 1999; Martell, 1975). Organic cocrystals involving NTA, however, have not been reported previously. We describe here the structure of a cocrystal of NTA, incorporating the organic base 1,10-phenanthroline, determined at 180 K.
The asymmetric unit and atomic numbering scheme for (I) are shown in Fig. 1. An intramolecular hydrogen bond is observed in the acid molecule, although the interaction is somewhat distorted from linearity (N1···O1 2.631 (1) Å and N1–H1···O1 115.6°). The location of H1 in a difference Fourier map suggests that intramolecular H-atom transfer occurs from the carboxylic acid group to the N atom [O1–C2 1.235 (2) Å and O2–C2 1.266 (2) Å]. Intermolecular H-atom transfer is also observed from the O5—C6—O6 carboxylic acid group to N2 in the phenanthroline base [O5–C6 1.248 (2) Å and O6–C6 1.253 (2) Å]. The O3—C4—O4 group is the only carboxylic acid group which remains protonated (Fig. 1).
Crinkled supramolecular tapes are formed along the c direction from acid molecules linked via O4i—H100···O2 hydrogen bonds [symmetry code: (i) -x + 1.5, -y + 0.5, z + 0.5]. Adjacent tapes are bound via hydrogen bonds through water molecules (Table 1) such that supramolecular sheets are formed parallel to the (100) plane (Fig. 2). The 1,10-phenanthroline molecule, furthermore, is bonded to O6 via an N2ii—H2···O6 hydrogen bond [Table 1; symmetry code: (ii) 1 - x, y, 0.5 - z]. The 1,10-phenanthroline molecules adopt a face-to-face stacking arrangement along the c direction.