Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705204X/hk2347sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705204X/hk2347Isup2.hkl |
CCDC reference: 1271213
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.133
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C1 .. 15.18 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C1 .. 22.61 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C2 .. 9.99 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C1 PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1 ... ?
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 3 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 5 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 general backgroud, see: Desiraju (1995); Desiraju (1997); Braga et al. (1998); Mccann et al. (1996); Mccann et al. (1995); Wai et al. (1990); Yaghi et al. (1996); Min & Lee (2002); Maira et al. (2001). For bond-length data, see: Allen et al. (1987).
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Lanthanum (III) nitrate hexahydrate (432.8 mg, 1 mmol), N-(2-benzamido)-2-carboxamido-benzoic acid (568.6 mg, 2 mmol), ammonia (0.5 mol/l, 4 ml) and distilled water (8 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol and allowed to air-dry at room temperature.
H atoms were positioned geometrically, with O—H = 0.82 Å (for OH), N—H = 0.86 Å (for NH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N,O), where x = 1.5 for OH H atom and x = 1.2 for all other H atoms.
In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to carboxyl groups are one of the most important classes of biological ligands, the coordination of metal-carboxyl groups complexes are of critical importance in biological systems, organic materials and coordination chemistry. Recently, carboxyl groups with variable coordination modes have been used to construct metal-organic supramolecular structures (Mccann et al., 1996; Mccann et al., 1995; Wai et al., 1990; Yaghi et al., 1996; Min & Lee 2002; Maira et al., 2001). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with N-(2-benzamido)-2-carboxamido-benzoic acid ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The rings A (C2—C7) and B (C10—C15) are, of course, planar and they are oriented at a dihedral angle of 8.01 (3)°.
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of a supramolecular network structure.
For general backgroud, see: Desiraju (1995); Desiraju (1997); Braga et al. (1998); Mccann et al. (1996); Mccann et al. (1995); Wai et al. (1990); Yaghi et al. (1996); Min & Lee (2002); Maira et al. (2001). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
C15H12N2O4 | F(000) = 592 |
Mr = 284.27 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 1987 reflections |
a = 8.1489 (15) Å | θ = 2.4–21.0° |
b = 12.9061 (11) Å | µ = 0.10 mm−1 |
c = 12.8993 (12) Å | T = 273 K |
β = 92.669 (4)° | Prism, colorless |
V = 1355.2 (3) Å3 | 0.28 × 0.18 × 0.15 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2844 independent reflections |
Radiation source: fine-focus sealed tube | 1313 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 27.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.972, Tmax = 0.985 | k = −16→16 |
9163 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.0776P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2844 reflections | Δρmax = 0.24 e Å−3 |
192 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0094 (16) |
C15H12N2O4 | V = 1355.2 (3) Å3 |
Mr = 284.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.1489 (15) Å | µ = 0.10 mm−1 |
b = 12.9061 (11) Å | T = 273 K |
c = 12.8993 (12) Å | 0.28 × 0.18 × 0.15 mm |
β = 92.669 (4)° |
Bruker SMART CCD area-detector diffractometer | 2844 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1313 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.985 | Rint = 0.044 |
9163 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.24 e Å−3 |
2844 reflections | Δρmin = −0.21 e Å−3 |
192 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 | 0.7542 (4) | −0.37592 (18) | 0.54854 (18) | 0.1346 (9) | |
H1 | 0.7767 | −0.3888 | 0.4886 | 0.202* | |
O2 | 0.8669 (2) | −0.23458 (15) | 0.51418 (13) | 0.0873 (6) | |
O3 | 0.9292 (2) | −0.01113 (12) | 0.62646 (12) | 0.0645 (5) | |
O4 | 0.5678 (2) | 0.15831 (12) | 0.51278 (13) | 0.0691 (5) | |
N1 | 0.7074 (2) | −0.02917 (14) | 0.51870 (15) | 0.0637 (6) | |
H1A | 0.6170 | −0.0619 | 0.5052 | 0.076* | |
N2 | 0.7560 (2) | 0.04919 (14) | 0.45305 (14) | 0.0637 (6) | |
H2A | 0.8314 | 0.0382 | 0.4099 | 0.076* | |
C1 | 0.7822 (3) | −0.28611 (16) | 0.56705 (17) | 0.0503 (6) | |
C2 | 0.7146 (3) | −0.23995 (16) | 0.65641 (16) | 0.0540 (6) | |
C3 | 0.6407 (3) | −0.30410 (17) | 0.72595 (19) | 0.0622 (7) | |
H3 | 0.6333 | −0.3749 | 0.7132 | 0.075* | |
C4 | 0.5796 (3) | −0.26387 (18) | 0.81212 (18) | 0.0650 (7) | |
H4 | 0.5313 | −0.3071 | 0.8597 | 0.078* | |
C5 | 0.5881 (3) | −0.15840 (19) | 0.83039 (18) | 0.0681 (7) | |
H5 | 0.5439 | −0.1309 | 0.8896 | 0.082* | |
C6 | 0.6616 (3) | −0.09405 (18) | 0.76139 (17) | 0.0620 (6) | |
H6 | 0.6678 | −0.0234 | 0.7750 | 0.074* | |
C7 | 0.7262 (3) | −0.13252 (15) | 0.67258 (16) | 0.0505 (6) | |
C8 | 0.8005 (3) | −0.05369 (16) | 0.60246 (18) | 0.0529 (6) | |
C9 | 0.6826 (3) | 0.14349 (18) | 0.45807 (17) | 0.0549 (6) | |
C10 | 0.7452 (3) | 0.22494 (17) | 0.38889 (17) | 0.0576 (6) | |
C11 | 0.8233 (3) | 0.2020 (2) | 0.3001 (2) | 0.0706 (7) | |
H11 | 0.8413 | 0.1335 | 0.2814 | 0.085* | |
C12 | 0.8755 (3) | 0.2832 (3) | 0.2380 (2) | 0.0939 (10) | |
H12 | 0.9285 | 0.2686 | 0.1774 | 0.113* | |
C13 | 0.8493 (5) | 0.3839 (3) | 0.2657 (3) | 0.1095 (13) | |
H13 | 0.8837 | 0.4372 | 0.2233 | 0.131* | |
C14 | 0.7743 (5) | 0.4064 (2) | 0.3534 (3) | 0.1063 (11) | |
H14 | 0.7603 | 0.4752 | 0.3726 | 0.128* | |
C15 | 0.7178 (3) | 0.3281 (2) | 0.4152 (2) | 0.0795 (8) | |
H15 | 0.6616 | 0.3441 | 0.4742 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.213 (3) | 0.0746 (15) | 0.1225 (19) | −0.0185 (15) | 0.0767 (17) | −0.0326 (13) |
O2 | 0.1097 (15) | 0.0780 (13) | 0.0771 (12) | 0.0115 (11) | 0.0352 (11) | −0.0096 (10) |
O3 | 0.0654 (11) | 0.0509 (10) | 0.0779 (11) | −0.0094 (8) | 0.0106 (8) | −0.0019 (8) |
O4 | 0.0708 (12) | 0.0628 (11) | 0.0752 (11) | −0.0048 (9) | 0.0171 (9) | 0.0010 (8) |
N1 | 0.0635 (13) | 0.0541 (12) | 0.0739 (14) | −0.0105 (10) | 0.0069 (11) | 0.0224 (10) |
N2 | 0.0706 (13) | 0.0523 (12) | 0.0698 (13) | −0.0016 (10) | 0.0226 (10) | 0.0179 (10) |
C1 | 0.0723 (16) | 0.0277 (11) | 0.0529 (13) | −0.0017 (11) | 0.0249 (12) | −0.0042 (10) |
C2 | 0.0598 (14) | 0.0436 (13) | 0.0590 (14) | 0.0042 (11) | 0.0090 (11) | 0.0035 (11) |
C3 | 0.0760 (17) | 0.0393 (12) | 0.0719 (16) | 0.0011 (11) | 0.0095 (13) | 0.0095 (11) |
C4 | 0.0781 (17) | 0.0572 (16) | 0.0609 (16) | 0.0009 (13) | 0.0154 (13) | 0.0148 (12) |
C5 | 0.0829 (18) | 0.0649 (17) | 0.0580 (15) | 0.0062 (14) | 0.0199 (12) | 0.0024 (12) |
C6 | 0.0769 (17) | 0.0475 (14) | 0.0631 (15) | 0.0004 (12) | 0.0195 (12) | −0.0018 (11) |
C7 | 0.0570 (14) | 0.0400 (12) | 0.0552 (14) | −0.0003 (10) | 0.0099 (11) | 0.0047 (10) |
C8 | 0.0594 (15) | 0.0365 (12) | 0.0640 (15) | 0.0009 (12) | 0.0152 (12) | −0.0016 (11) |
C9 | 0.0575 (15) | 0.0510 (15) | 0.0562 (14) | −0.0065 (12) | 0.0019 (12) | 0.0025 (11) |
C10 | 0.0596 (15) | 0.0491 (14) | 0.0637 (15) | −0.0077 (11) | −0.0023 (12) | 0.0119 (11) |
C11 | 0.0736 (18) | 0.0697 (17) | 0.0688 (17) | −0.0063 (13) | 0.0065 (13) | 0.0221 (13) |
C12 | 0.084 (2) | 0.118 (3) | 0.080 (2) | −0.0162 (19) | 0.0002 (15) | 0.0407 (19) |
C13 | 0.123 (3) | 0.089 (3) | 0.114 (3) | −0.039 (2) | −0.027 (2) | 0.052 (2) |
C14 | 0.147 (3) | 0.0493 (17) | 0.119 (3) | −0.0257 (19) | −0.030 (2) | 0.0241 (19) |
C15 | 0.093 (2) | 0.0544 (17) | 0.0899 (19) | −0.0070 (14) | −0.0115 (15) | 0.0081 (14) |
O1—C1 | 1.203 (3) | C5—C6 | 1.375 (3) |
O1—H1 | 0.8200 | C5—H5 | 0.9300 |
O2—C1 | 1.195 (2) | C6—C7 | 1.375 (3) |
O3—C8 | 1.211 (2) | C6—H6 | 0.9300 |
O4—C9 | 1.212 (3) | C7—C8 | 1.507 (3) |
N1—C8 | 1.329 (3) | C9—C10 | 1.485 (3) |
N1—N2 | 1.389 (2) | C10—C11 | 1.368 (3) |
N1—H1A | 0.8600 | C10—C15 | 1.395 (3) |
N2—C9 | 1.359 (3) | C11—C12 | 1.397 (3) |
N2—H2A | 0.8600 | C11—H11 | 0.9300 |
C1—C2 | 1.430 (3) | C12—C13 | 1.367 (5) |
C2—C3 | 1.380 (3) | C12—H12 | 0.9300 |
C2—C7 | 1.405 (3) | C13—C14 | 1.343 (5) |
C3—C4 | 1.344 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.379 (4) |
C4—C5 | 1.383 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C1—O1—H1 | 109.5 | C6—C7—C8 | 115.86 (19) |
C8—N1—N2 | 120.05 (18) | C2—C7—C8 | 127.10 (19) |
C8—N1—H1A | 120.0 | O3—C8—N1 | 123.7 (2) |
N2—N1—H1A | 120.0 | O3—C8—C7 | 121.3 (2) |
C9—N2—N1 | 118.97 (19) | N1—C8—C7 | 114.7 (2) |
C9—N2—H2A | 120.5 | O4—C9—N2 | 121.5 (2) |
N1—N2—H2A | 120.5 | O4—C9—C10 | 122.3 (2) |
O2—C1—O1 | 122.2 (2) | N2—C9—C10 | 116.1 (2) |
O2—C1—C2 | 118.8 (2) | C11—C10—C15 | 119.8 (2) |
O1—C1—C2 | 119.0 (2) | C11—C10—C9 | 122.4 (2) |
C3—C2—C7 | 121.6 (2) | C15—C10—C9 | 117.8 (2) |
C3—C2—C1 | 118.0 (2) | C10—C11—C12 | 118.9 (3) |
C7—C2—C1 | 120.35 (19) | C10—C11—H11 | 120.5 |
C4—C3—C2 | 119.7 (2) | C12—C11—H11 | 120.5 |
C4—C3—H3 | 120.1 | C13—C12—C11 | 120.5 (3) |
C2—C3—H3 | 120.1 | C13—C12—H12 | 119.7 |
C3—C4—C5 | 120.3 (2) | C11—C12—H12 | 119.7 |
C3—C4—H4 | 119.9 | C14—C13—C12 | 120.6 (3) |
C5—C4—H4 | 119.9 | C14—C13—H13 | 119.7 |
C6—C5—C4 | 120.3 (2) | C12—C13—H13 | 119.7 |
C6—C5—H5 | 119.9 | C13—C14—C15 | 120.4 (3) |
C4—C5—H5 | 119.9 | C13—C14—H14 | 119.8 |
C5—C6—C7 | 121.1 (2) | C15—C14—H14 | 119.8 |
C5—C6—H6 | 119.5 | C14—C15—C10 | 119.8 (3) |
C7—C6—H6 | 119.5 | C14—C15—H15 | 120.1 |
C6—C7—C2 | 117.03 (19) | C10—C15—H15 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.86 | 1.96 | 2.809 (2) | 169 |
N2—H2A···O3ii | 0.86 | 2.06 | 2.849 (2) | 153 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H12N2O4 |
Mr | 284.27 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 8.1489 (15), 12.9061 (11), 12.8993 (12) |
β (°) | 92.669 (4) |
V (Å3) | 1355.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.28 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.972, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9163, 2844, 1313 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.133, 0.99 |
No. of reflections | 2844 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.21 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.86 | 1.96 | 2.809 (2) | 169 |
N2—H2A···O3ii | 0.86 | 2.06 | 2.849 (2) | 153 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1. |
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In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to carboxyl groups are one of the most important classes of biological ligands, the coordination of metal-carboxyl groups complexes are of critical importance in biological systems, organic materials and coordination chemistry. Recently, carboxyl groups with variable coordination modes have been used to construct metal-organic supramolecular structures (Mccann et al., 1996; Mccann et al., 1995; Wai et al., 1990; Yaghi et al., 1996; Min & Lee 2002; Maira et al., 2001). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with N-(2-benzamido)-2-carboxamido-benzoic acid ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The rings A (C2—C7) and B (C10—C15) are, of course, planar and they are oriented at a dihedral angle of 8.01 (3)°.
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of a supramolecular network structure.