The crystal structure of the title compound, C
17H
18N
2O
4, is presented. The molecule sits on a crystallographic twofold rotation axis. It contains O
H—N intramolecular hydrogen bonds typical of
ortho-benzoic amino acids; O
H—O intermolecular hydrogen bonds connect the molecules into infinite chains.
Supporting information
CCDC reference: 238702
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.118
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT703_ALERT_1_C Torsion Calc 174.86(9), Rep 175.00(10), Dev.. 1.56 Sigma
N10 -C11 -C12 -C11 1.555 1.555 1.555 2.555
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
2 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
2,2'-(Propane-1,3-diimino)dibenzoic acid
top
Crystal data top
C17H18N2O4 | Dx = 1.369 Mg m−3 |
Mr = 314.33 | Melting point: 200.5 K |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 4874 reflections |
a = 11.9318 (18) Å | θ = 2.2–26.0° |
b = 14.152 (2) Å | µ = 0.10 mm−1 |
c = 9.0323 (14) Å | T = 100 K |
V = 1525.2 (4) Å3 | Block, yellow |
Z = 4 | 0.48 × 0.17 × 0.16 mm |
F(000) = 664 | |
Data collection top
Bruker Apex CCD area-detector diffractometer | 1504 independent reflections |
Radiation source: fine-focus sealed tube | 1382 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −14→13 |
Tmin = 0.954, Tmax = 0.984 | k = −17→16 |
8887 measured reflections | l = −11→11 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.67P] where P = (Fo2 + 2Fc2)/3 |
1504 reflections | (Δ/σ)max < 0.001 |
105 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | −0.00109 (8) | 0.60117 (6) | 0.87857 (11) | 0.0299 (3) | |
H1 | −0.0243 | 0.5726 | 0.9691 | 0.036* | |
C2 | 0.04850 (11) | 0.53332 (9) | 0.80214 (15) | 0.0238 (3) | |
O3 | 0.05625 (8) | 0.45211 (6) | 0.85268 (10) | 0.0265 (3) | |
C4 | 0.09160 (11) | 0.56161 (9) | 0.65702 (14) | 0.0236 (3) | |
C5 | 0.07945 (12) | 0.65648 (9) | 0.61282 (16) | 0.0276 (3) | |
H5 | 0.0457 | 0.7004 | 0.6787 | 0.033* | |
C6 | 0.11548 (13) | 0.68686 (10) | 0.47600 (17) | 0.0327 (4) | |
H6 | 0.1082 | 0.7513 | 0.4482 | 0.039* | |
C7 | 0.16278 (12) | 0.62161 (10) | 0.37911 (16) | 0.0312 (4) | |
H7 | 0.1857 | 0.6418 | 0.2835 | 0.037* | |
C8 | 0.17698 (11) | 0.52867 (10) | 0.41875 (16) | 0.0268 (3) | |
H8 | 0.2090 | 0.4856 | 0.3501 | 0.032* | |
C9 | 0.14443 (11) | 0.49629 (9) | 0.56085 (14) | 0.0230 (3) | |
N10 | 0.16511 (10) | 0.40530 (7) | 0.60348 (13) | 0.0260 (3) | |
H10 | 0.1497 | 0.3897 | 0.6956 | 0.031* | |
C11 | 0.21071 (12) | 0.33265 (8) | 0.50771 (14) | 0.0248 (3) | |
H11A | 0.2744 | 0.3585 | 0.4503 | 0.030* | |
H11B | 0.1526 | 0.3112 | 0.4371 | 0.030* | |
C12 | 0.2500 | 0.2500 | 0.6012 (2) | 0.0258 (4) | |
H12A | 0.3123 | 0.2710 | 0.6658 | 0.031* | 0.50 |
H12B | 0.1877 | 0.2290 | 0.6658 | 0.031* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0415 (6) | 0.0204 (5) | 0.0278 (5) | 0.0034 (4) | 0.0075 (4) | −0.0009 (4) |
C2 | 0.0259 (7) | 0.0202 (6) | 0.0253 (7) | −0.0001 (5) | −0.0027 (5) | −0.0038 (5) |
O3 | 0.0362 (6) | 0.0190 (5) | 0.0242 (5) | 0.0019 (4) | 0.0032 (4) | −0.0005 (4) |
C4 | 0.0247 (7) | 0.0212 (7) | 0.0248 (7) | −0.0015 (5) | −0.0025 (5) | −0.0002 (5) |
C5 | 0.0291 (7) | 0.0216 (6) | 0.0322 (7) | 0.0034 (5) | −0.0006 (5) | −0.0004 (5) |
C6 | 0.0363 (8) | 0.0231 (7) | 0.0387 (8) | 0.0044 (6) | 0.0023 (6) | 0.0082 (6) |
C7 | 0.0327 (8) | 0.0307 (8) | 0.0302 (7) | 0.0027 (6) | 0.0040 (6) | 0.0088 (6) |
C8 | 0.0277 (7) | 0.0248 (7) | 0.0278 (7) | 0.0027 (5) | 0.0017 (5) | 0.0023 (5) |
C9 | 0.0240 (6) | 0.0197 (6) | 0.0252 (7) | −0.0008 (5) | −0.0024 (5) | 0.0013 (5) |
N10 | 0.0373 (7) | 0.0197 (6) | 0.0211 (6) | 0.0011 (5) | 0.0035 (4) | −0.0003 (4) |
C11 | 0.0306 (7) | 0.0199 (6) | 0.0240 (7) | 0.0014 (5) | 0.0028 (5) | −0.0012 (5) |
C12 | 0.0355 (10) | 0.0213 (9) | 0.0205 (8) | −0.0011 (8) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C2 | 1.322 (2) | C7—H7 | 0.9500 |
O1—H1 | 0.9531 | C8—C9 | 1.4171 (19) |
C2—O3 | 1.240 (2) | C8—H8 | 0.9500 |
C2—C4 | 1.464 (2) | C9—N10 | 1.366 (2) |
C4—C5 | 1.408 (2) | N10—C11 | 1.450 (2) |
C4—C9 | 1.416 (2) | N10—H10 | 0.8800 |
C5—C6 | 1.377 (2) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.392 (2) | C12—C11i | 1.5171 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3736 (19) | C12—H12B | 0.9900 |
| | | |
C2—O1—H1 | 105.7 | N10—C9—C4 | 121.5 (1) |
O3—C2—O1 | 120.9 (1) | N10—C9—C8 | 120.7 (1) |
O3—C2—C4 | 123.8 (1) | C4—C9—C8 | 117.8 (1) |
O1—C2—C4 | 115.2 (1) | C9—N10—C11 | 124.6 (1) |
C5—C4—C9 | 119.6 (1) | C9—N10—H10 | 117.7 |
C5—C4—C2 | 118.6 (1) | C11—N10—H10 | 117.7 |
C9—C4—C2 | 121.8 (1) | N10—C11—C12 | 109.3 (1) |
C6—C5—C4 | 121.33 (13) | N10—C11—H11A | 109.8 |
C6—C5—H5 | 119.3 | C12—C11—H11A | 109.8 |
C4—C5—H5 | 119.3 | N10—C11—H11B | 109.8 |
C5—C6—C7 | 118.92 (12) | C12—C11—H11B | 109.8 |
C5—C6—H6 | 120.5 | H11A—C11—H11B | 108.3 |
C7—C6—H6 | 120.5 | C11i—C12—C11 | 112.3 (1) |
C8—C7—C6 | 121.43 (13) | C11i—C12—H12A | 109.1 |
C8—C7—H7 | 119.3 | C11—C12—H12A | 109.1 |
C6—C7—H7 | 119.3 | C11i—C12—H12B | 109.1 |
C7—C8—C9 | 120.79 (13) | C11—C12—H12B | 109.1 |
C7—C8—H8 | 119.6 | H12A—C12—H12B | 107.9 |
C9—C8—H8 | 119.6 | | |
| | | |
O3—C2—C4—C5 | −178.91 (12) | C2—C4—C9—N10 | −4.9 (2) |
O1—C2—C4—C5 | 1.33 (18) | C5—C4—C9—C8 | −3.82 (19) |
O3—C2—C4—C9 | 1.3 (2) | C2—C4—C9—C8 | 175.99 (12) |
O1—C2—C4—C9 | −178.5 (1) | C7—C8—C9—N10 | −175.81 (13) |
C9—C4—C5—C6 | 1.6 (2) | C7—C8—C9—C4 | 3.3 (2) |
C2—C4—C5—C6 | −178.19 (13) | C4—C9—N10—C11 | 175.0 (1) |
C4—C5—C6—C7 | 1.2 (2) | C8—C9—N10—C11 | −6.0 (2) |
C5—C6—C7—C8 | −1.9 (2) | C9—N10—C11—C12 | 165.34 (11) |
C6—C7—C8—C9 | −0.5 (2) | N10—C11—C12—C11i | 175.0 (1) |
C5—C4—C9—N10 | 175.26 (12) | | |
Symmetry code: (i) −x+1/2, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3ii | 0.95 | 1.69 | 2.626 (1) | 166 |
N10—H10···O3 | 0.88 | 2.01 | 2.682 (1) | 132 |
Symmetry code: (ii) −x, −y+1, −z+2. |