Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045497/bt2506sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045497/bt2506Isup2.hkl |
CCDC reference: 664213
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.117
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6516 Proportion of unique data used 0.5516 Ratio reflections to parameters 9.0192 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.02
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 2 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
For related literature, see: Alexiou et al. (2002); Gaynor et al. (2002); Lah & Pecoraro (1989); Lehaire et al. (2002); Liu et al. (2001); Saalfrank et al. (2001).
Benzoic acid anhydride (13.56 g, 60.0 mmol) and 3-hydroxynaphthalene-2-carbohydrazide (11.3 g, 56.0 mmol) were added to 120 ml of chloroform with an external ice-water bath. The reaction mixture was slowly warmed to room temperature and stirred for 8 h. After leaving overnight in a refrigerator, the resulting white precipitate was filtered off and rinsed with chloroform and diethyl ether (yield: 95.3%; m.p. 492–496 K). Calculatedd for C18H14N2O3: C 70.58, H 4.61, N 9.15%; found: C 70.24, H 4.75, N 9.02%.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93%A; N—H = 0.86 Å; O—H = 0.82 Å) and Uiso(H) values weren set equal to 1.2 Ueq(C, N) and 1.5Ueq(O).
Metallacrowns are a new class of metallamacrocycles, which have gained increasing attention over the past decade because of their unique properties (Alexiou et al., 2002; Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002; Liu et al., 2001; Saalfrank et al., 2001). These metallacrowns exhibit selective recognition of cations and anions (Saalfrank et al., 2001; Lehaire et al., 2002), can display intramolecular magnetic exchange interactions (Liu et al., 2001), and can be used as building blocks for twodimensional or three-dimensional network structures (Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002). The ability to control the generation of metallacrowns with different nuclear numbers, desired structures, and properties is still a substantial challenge. We now report structure of a designed pentadentate ligand.
The molecular structure of the title compound is illustrated in Fig.1. The bond lengths and bond angles are within normal ranges. The dihedral angel between the naphthalene and benzene planes is 4.3 (2)°. The molecular conformation is characterized by an N—H···O hydrogen bond and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.
For related literature, see: Alexiou et al. (2002); Gaynor et al. (2002); Lah & Pecoraro (1989); Lehaire et al. (2002); Liu et al. (2001); Saalfrank et al. (2001).
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Bruker, 1998).
Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C18H14N2O3 | F(000) = 640 |
Mr = 306.31 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/c | Melting point = 219–223 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8473 (10) Å | Cell parameters from 8325 reflections |
b = 33.907 (7) Å | θ = 6.0–27.6° |
c = 8.9148 (18) Å | µ = 0.10 mm−1 |
β = 91.61 (3)° | T = 273 K |
V = 1464.6 (5) Å3 | Block, colourless |
Z = 4 | 0.57 × 0.39 × 0.31 mm |
Rigaku R-AXIS RAPID diffractometer | 3401 independent reflections |
Radiation source: fine-focus sealed tube | 2414 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 0 pixels mm-1 | θmax = 27.6°, θmin = 3.3° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −44→44 |
Tmin = 0.936, Tmax = 0.976 | l = −11→11 |
7743 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.5358P] where P = (Fo2 + 2Fc2)/3 |
3401 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C18H14N2O3 | V = 1464.6 (5) Å3 |
Mr = 306.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.8473 (10) Å | µ = 0.10 mm−1 |
b = 33.907 (7) Å | T = 273 K |
c = 8.9148 (18) Å | 0.57 × 0.39 × 0.31 mm |
β = 91.61 (3)° |
Rigaku R-AXIS RAPID diffractometer | 3401 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2414 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.976 | Rint = 0.069 |
7743 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
3401 reflections | Δρmin = −0.18 e Å−3 |
208 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 | ||
C1 | 0.3553 (9) | 0.97519 (9) | 0.8154 (4) | 0.0902 (12) | |
H1B | 0.4486 | 0.9957 | 0.8639 | 0.108* | |
C2 | 0.0784 (6) | 0.91469 (9) | 0.6775 (4) | 0.0685 (9) | |
H2B | −0.0180 | 0.8943 | 0.6301 | 0.082* | |
C3 | 0.0072 (7) | 0.95336 (11) | 0.6456 (4) | 0.0884 (11) | |
H3B | −0.1360 | 0.9589 | 0.5773 | 0.106* | |
C4 | 0.1484 (9) | 0.98325 (10) | 0.7151 (5) | 0.0905 (12) | |
H4A | 0.1025 | 1.0093 | 0.6935 | 0.109* | |
C5 | 0.4286 (7) | 0.93649 (8) | 0.8464 (4) | 0.0707 (9) | |
H5A | 0.5734 | 0.9311 | 0.9140 | 0.085* | |
C6 | 0.2887 (5) | 0.90608 (7) | 0.7777 (3) | 0.0464 (7) | |
C7 | 0.3757 (5) | 0.86499 (7) | 0.8103 (3) | 0.0435 (6) | |
C8 | 0.1220 (5) | 0.76940 (7) | 0.7606 (3) | 0.0403 (6) | |
C9 | 0.2169 (5) | 0.72870 (7) | 0.7964 (3) | 0.0385 (6) | |
C10 | 0.5067 (5) | 0.68088 (7) | 0.9256 (3) | 0.0469 (7) | |
H10A | 0.6467 | 0.6752 | 0.9957 | 0.056* | |
C11 | 0.4322 (5) | 0.71903 (7) | 0.9015 (3) | 0.0417 (6) | |
C12 | 0.0889 (5) | 0.69841 (7) | 0.7208 (3) | 0.0454 (7) | |
H12A | −0.0537 | 0.7044 | 0.6527 | 0.054* | |
C13 | 0.1627 (5) | 0.65876 (7) | 0.7414 (3) | 0.0431 (6) | |
C14 | 0.3760 (5) | 0.64988 (7) | 0.8464 (3) | 0.0457 (7) | |
C15 | 0.4518 (6) | 0.60999 (8) | 0.8667 (4) | 0.0624 (8) | |
H15A | 0.5928 | 0.6036 | 0.9353 | 0.075* | |
C16 | 0.0314 (6) | 0.62774 (8) | 0.6613 (3) | 0.0576 (8) | |
H16A | −0.1112 | 0.6333 | 0.5927 | 0.069* | |
C17 | 0.1121 (6) | 0.58983 (8) | 0.6841 (3) | 0.0638 (8) | |
H17A | 0.0261 | 0.5696 | 0.6299 | 0.077* | |
C18 | 0.3226 (6) | 0.58093 (8) | 0.7879 (4) | 0.0673 (9) | |
H18A | 0.3750 | 0.5548 | 0.8033 | 0.081* | |
O1 | 0.6144 (3) | 0.85645 (5) | 0.8467 (2) | 0.0635 (6) | |
O2 | −0.0689 (4) | 0.77662 (5) | 0.6712 (2) | 0.0607 (6) | |
O3 | 0.5609 (3) | 0.74934 (5) | 0.9766 (2) | 0.0548 (5) | |
H3A | 0.6758 | 0.7404 | 1.0367 | 0.082* | |
N1 | 0.1807 (4) | 0.83749 (6) | 0.7983 (2) | 0.0471 (6) | |
H1A | 0.0145 | 0.8436 | 0.7710 | 0.056* | |
N2 | 0.2512 (4) | 0.79894 (6) | 0.8305 (2) | 0.0474 (6) | |
H2A | 0.3797 | 0.7940 | 0.8963 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.135 (3) | 0.045 (2) | 0.090 (3) | −0.012 (2) | 0.001 (3) | −0.0035 (19) |
C2 | 0.0663 (19) | 0.0537 (18) | 0.085 (2) | −0.0009 (15) | −0.0127 (18) | 0.0181 (16) |
C3 | 0.086 (2) | 0.068 (2) | 0.110 (3) | 0.012 (2) | −0.015 (2) | 0.032 (2) |
C4 | 0.119 (3) | 0.054 (2) | 0.100 (3) | 0.021 (2) | 0.020 (3) | 0.020 (2) |
C5 | 0.083 (2) | 0.0514 (19) | 0.077 (2) | −0.0081 (17) | −0.0127 (18) | 0.0005 (16) |
C6 | 0.0409 (15) | 0.0427 (15) | 0.0557 (18) | 0.0002 (12) | 0.0008 (14) | 0.0035 (13) |
C7 | 0.0352 (15) | 0.0459 (15) | 0.0488 (16) | −0.0003 (13) | −0.0062 (12) | −0.0019 (12) |
C8 | 0.0356 (13) | 0.0444 (15) | 0.0404 (15) | −0.0007 (12) | −0.0094 (13) | −0.0014 (12) |
C9 | 0.0350 (13) | 0.0407 (14) | 0.0394 (15) | 0.0005 (11) | −0.0060 (12) | 0.0016 (12) |
C10 | 0.0439 (14) | 0.0448 (16) | 0.0511 (16) | 0.0045 (12) | −0.0141 (13) | 0.0051 (13) |
C11 | 0.0411 (14) | 0.0410 (15) | 0.0424 (15) | −0.0030 (12) | −0.0070 (12) | −0.0020 (12) |
C12 | 0.0426 (15) | 0.0472 (16) | 0.0457 (16) | −0.0019 (12) | −0.0101 (13) | 0.0019 (13) |
C13 | 0.0447 (15) | 0.0402 (15) | 0.0443 (15) | −0.0039 (12) | 0.0011 (13) | −0.0016 (12) |
C14 | 0.0426 (15) | 0.0427 (15) | 0.0518 (16) | 0.0031 (12) | −0.0001 (13) | 0.0031 (13) |
C15 | 0.0633 (19) | 0.0454 (17) | 0.078 (2) | 0.0051 (14) | −0.0099 (16) | 0.0045 (15) |
C16 | 0.0643 (19) | 0.0491 (18) | 0.0589 (18) | −0.0085 (14) | −0.0060 (15) | −0.0029 (14) |
C17 | 0.072 (2) | 0.0476 (18) | 0.072 (2) | −0.0113 (15) | 0.0003 (18) | −0.0118 (15) |
C18 | 0.074 (2) | 0.0413 (16) | 0.087 (2) | 0.0031 (16) | 0.0009 (19) | −0.0037 (16) |
O1 | 0.0357 (10) | 0.0544 (12) | 0.0995 (17) | 0.0012 (9) | −0.0154 (10) | 0.0020 (11) |
O2 | 0.0610 (12) | 0.0479 (11) | 0.0709 (14) | 0.0019 (9) | −0.0377 (11) | −0.0008 (9) |
O3 | 0.0550 (11) | 0.0443 (10) | 0.0634 (12) | 0.0041 (9) | −0.0303 (10) | 0.0009 (9) |
N1 | 0.0340 (11) | 0.0389 (12) | 0.0673 (15) | 0.0032 (10) | −0.0172 (10) | 0.0033 (11) |
N2 | 0.0442 (12) | 0.0371 (12) | 0.0593 (14) | 0.0040 (10) | −0.0249 (11) | 0.0021 (11) |
C1—C4 | 1.352 (5) | C10—C14 | 1.407 (3) |
C1—C5 | 1.385 (4) | C10—H10A | 0.9300 |
C1—H1B | 0.9300 | C11—O3 | 1.368 (3) |
C2—C6 | 1.368 (4) | C12—C13 | 1.402 (3) |
C2—C3 | 1.383 (4) | C12—H12A | 0.9300 |
C2—H2B | 0.9300 | C13—C14 | 1.408 (4) |
C3—C4 | 1.362 (5) | C13—C16 | 1.413 (4) |
C3—H3B | 0.9300 | C14—C15 | 1.412 (4) |
C4—H4A | 0.9300 | C15—C18 | 1.353 (4) |
C5—C6 | 1.369 (4) | C15—H15A | 0.9300 |
C5—H5A | 0.9300 | C16—C17 | 1.357 (4) |
C6—C7 | 1.482 (3) | C16—H16A | 0.9300 |
C7—O1 | 1.227 (3) | C17—C18 | 1.392 (4) |
C7—N1 | 1.330 (3) | C17—H17A | 0.9300 |
C8—O2 | 1.229 (3) | C18—H18A | 0.9300 |
C8—N2 | 1.327 (3) | O3—H3A | 0.8200 |
C8—C9 | 1.487 (3) | N1—N2 | 1.379 (3) |
C9—C12 | 1.367 (3) | N1—H1A | 0.8600 |
C9—C11 | 1.421 (3) | N2—H2A | 0.8600 |
C10—C11 | 1.358 (3) | ||
C4—C1—C5 | 120.3 (3) | C10—C11—C9 | 120.7 (2) |
C4—C1—H1B | 119.8 | O3—C11—C9 | 117.8 (2) |
C5—C1—H1B | 119.8 | C9—C12—C13 | 123.0 (2) |
C6—C2—C3 | 120.9 (3) | C9—C12—H12A | 118.5 |
C6—C2—H2B | 119.6 | C13—C12—H12A | 118.5 |
C3—C2—H2B | 119.6 | C12—C13—C14 | 118.2 (2) |
C4—C3—C2 | 119.5 (3) | C12—C13—C16 | 122.6 (2) |
C4—C3—H3B | 120.2 | C14—C13—C16 | 119.3 (2) |
C2—C3—H3B | 120.2 | C10—C14—C13 | 119.1 (2) |
C1—C4—C3 | 120.3 (3) | C10—C14—C15 | 122.7 (2) |
C1—C4—H4A | 119.9 | C13—C14—C15 | 118.3 (2) |
C3—C4—H4A | 119.9 | C18—C15—C14 | 121.1 (3) |
C6—C5—C1 | 120.2 (3) | C18—C15—H15A | 119.5 |
C6—C5—H5A | 119.9 | C14—C15—H15A | 119.5 |
C1—C5—H5A | 119.9 | C17—C16—C13 | 120.4 (3) |
C2—C6—C5 | 118.8 (3) | C17—C16—H16A | 119.8 |
C2—C6—C7 | 122.1 (2) | C13—C16—H16A | 119.8 |
C5—C6—C7 | 119.0 (2) | C16—C17—C18 | 120.5 (3) |
O1—C7—N1 | 121.2 (2) | C16—C17—H17A | 119.7 |
O1—C7—C6 | 122.3 (2) | C18—C17—H17A | 119.7 |
N1—C7—C6 | 116.4 (2) | C15—C18—C17 | 120.5 (3) |
O2—C8—N2 | 119.4 (2) | C15—C18—H18A | 119.8 |
O2—C8—C9 | 123.1 (2) | C17—C18—H18A | 119.8 |
N2—C8—C9 | 117.4 (2) | C11—O3—H3A | 109.5 |
C12—C9—C11 | 117.8 (2) | C7—N1—N2 | 118.4 (2) |
C12—C9—C8 | 117.3 (2) | C7—N1—H1A | 120.8 |
C11—C9—C8 | 124.9 (2) | N2—N1—H1A | 120.8 |
C11—C10—C14 | 121.2 (2) | C8—N2—N1 | 120.4 (2) |
C11—C10—H10A | 119.4 | C8—N2—H2A | 119.8 |
C14—C10—H10A | 119.4 | N1—N2—H2A | 119.8 |
C10—C11—O3 | 121.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 | 2.12 | 2.864 (3) | 145 |
N2—H2A···O3 | 0.86 | 1.88 | 2.582 (3) | 138 |
O3—H3A···O2ii | 0.82 | 1.79 | 2.613 (3) | 177 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H14N2O3 |
Mr | 306.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 4.8473 (10), 33.907 (7), 8.9148 (18) |
β (°) | 91.61 (3) |
V (Å3) | 1464.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.57 × 0.39 × 0.31 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.936, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7743, 3401, 2414 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.117, 1.03 |
No. of reflections | 3401 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.8600 | 2.1200 | 2.864 (3) | 145.00 |
N2—H2A···O3 | 0.8600 | 1.8800 | 2.582 (3) | 138.00 |
O3—H3A···O2ii | 0.8200 | 1.7900 | 2.613 (3) | 177.00 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, −y+3/2, z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Metallacrowns are a new class of metallamacrocycles, which have gained increasing attention over the past decade because of their unique properties (Alexiou et al., 2002; Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002; Liu et al., 2001; Saalfrank et al., 2001). These metallacrowns exhibit selective recognition of cations and anions (Saalfrank et al., 2001; Lehaire et al., 2002), can display intramolecular magnetic exchange interactions (Liu et al., 2001), and can be used as building blocks for twodimensional or three-dimensional network structures (Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002). The ability to control the generation of metallacrowns with different nuclear numbers, desired structures, and properties is still a substantial challenge. We now report structure of a designed pentadentate ligand.
The molecular structure of the title compound is illustrated in Fig.1. The bond lengths and bond angles are within normal ranges. The dihedral angel between the naphthalene and benzene planes is 4.3 (2)°. The molecular conformation is characterized by an N—H···O hydrogen bond and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.