The crystal structure of the title compound, C
15H
9NO
4·-C
3H
7NO, comprises 4-phthalimidobenzoic acid and
N,
N-dimethylformamide (DMF) molecules, which are held together by an O—H
O hydrogen bond. The dihedral angle between the phthalimide group and the benzene ring is 53.5 (2)°.
Supporting information
CCDC reference: 624883
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2
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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
4-phthalimidobenzoic acid
N,
N-dimethylformamide solvate
top
Crystal data top
C15H9NO4·C3H7NO | Z = 2 |
Mr = 340.33 | F(000) = 356 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.926 (2) Å | Cell parameters from 1205 reflections |
b = 8.398 (3) Å | θ = 2.3–24.2° |
c = 17.518 (7) Å | µ = 0.10 mm−1 |
α = 95.986 (7)° | T = 294 K |
β = 90.837 (7)° | Block, colourless |
γ = 109.706 (6)° | 0.34 × 0.30 × 0.22 mm |
V = 815.1 (5) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2819 independent reflections |
Radiation source: fine-focus sealed tube | 1777 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 25.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→6 |
Tmin = 0.966, Tmax = 0.978 | k = −9→9 |
4122 measured reflections | l = −20→16 |
Refinement top
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.003 |
2819 reflections | Δρmax = 0.16 e Å−3 |
230 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.084 (7) |
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 | |
O1 | 0.2956 (3) | 0.5151 (2) | 0.28148 (10) | 0.0632 (5) | |
O2 | −0.2627 (3) | 0.7083 (2) | 0.39957 (10) | 0.0531 (5) | |
O3 | 0.6493 (3) | 1.3161 (2) | 0.18899 (11) | 0.0674 (6) | |
H3 | 0.6971 | 1.3931 | 0.1617 | 0.101* | |
O4 | 0.3022 (3) | 1.2693 (2) | 0.12474 (10) | 0.0650 (6) | |
N1 | 0.0353 (3) | 0.6494 (2) | 0.33016 (10) | 0.0407 (5) | |
C1 | 0.1346 (4) | 0.5178 (3) | 0.32191 (14) | 0.0455 (6) | |
C2 | −0.0007 (4) | 0.3912 (3) | 0.37239 (13) | 0.0414 (6) | |
C3 | 0.0274 (5) | 0.2407 (3) | 0.38827 (15) | 0.0540 (7) | |
H3A | 0.1432 | 0.2026 | 0.3653 | 0.065* | |
C4 | −0.1239 (5) | 0.1494 (3) | 0.43967 (16) | 0.0619 (8) | |
H4 | −0.1106 | 0.0472 | 0.4511 | 0.074* | |
C5 | −0.2934 (5) | 0.2060 (3) | 0.47422 (16) | 0.0610 (7) | |
H5 | −0.3901 | 0.1426 | 0.5094 | 0.073* | |
C6 | −0.3232 (4) | 0.3554 (3) | 0.45773 (15) | 0.0539 (7) | |
H6 | −0.4404 | 0.3925 | 0.4804 | 0.065* | |
C7 | −0.1723 (4) | 0.4478 (3) | 0.40625 (13) | 0.0416 (6) | |
C8 | −0.1522 (4) | 0.6145 (3) | 0.38066 (13) | 0.0407 (6) | |
C9 | 0.1278 (4) | 0.8023 (3) | 0.29410 (12) | 0.0381 (6) | |
C10 | −0.0224 (4) | 0.8552 (3) | 0.24937 (13) | 0.0429 (6) | |
H10 | −0.1866 | 0.7956 | 0.2448 | 0.051* | |
C11 | 0.0745 (4) | 0.9970 (3) | 0.21183 (13) | 0.0437 (6) | |
H11 | −0.0255 | 1.0327 | 0.1817 | 0.052* | |
C12 | 0.3182 (4) | 1.0871 (3) | 0.21821 (12) | 0.0383 (5) | |
C13 | 0.4649 (4) | 1.0348 (3) | 0.26478 (13) | 0.0452 (6) | |
H13 | 0.6285 | 1.0961 | 0.2705 | 0.054* | |
C14 | 0.3704 (4) | 0.8932 (3) | 0.30257 (13) | 0.0462 (6) | |
H14 | 0.4698 | 0.8589 | 0.3337 | 0.055* | |
C15 | 0.4194 (5) | 1.2340 (3) | 0.17302 (14) | 0.0467 (6) | |
O5 | −0.1464 (3) | 0.5513 (2) | 0.10432 (10) | 0.0618 (5) | |
N2 | 0.2143 (3) | 0.7066 (3) | 0.06563 (11) | 0.0493 (5) | |
C16 | 0.0733 (5) | 0.5874 (3) | 0.10307 (14) | 0.0519 (7) | |
H16 | 0.1436 | 0.5259 | 0.1306 | 0.062* | |
C17 | 0.4710 (5) | 0.7396 (5) | 0.06602 (19) | 0.0881 (11) | |
H17A | 0.5109 | 0.6636 | 0.0967 | 0.132* | |
H17B | 0.5549 | 0.8552 | 0.0872 | 0.132* | |
H17C | 0.5169 | 0.7218 | 0.0144 | 0.132* | |
C18 | 0.1187 (5) | 0.8050 (3) | 0.01969 (15) | 0.0610 (7) | |
H18A | −0.0535 | 0.7611 | 0.0185 | 0.091* | |
H18B | 0.1714 | 0.7972 | −0.0317 | 0.091* | |
H18C | 0.1749 | 0.9219 | 0.0418 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0710 (12) | 0.0639 (12) | 0.0650 (12) | 0.0353 (10) | 0.0226 (10) | 0.0095 (10) |
O2 | 0.0558 (10) | 0.0463 (10) | 0.0640 (12) | 0.0245 (9) | 0.0148 (9) | 0.0118 (9) |
O3 | 0.0518 (11) | 0.0709 (13) | 0.0773 (14) | 0.0092 (10) | 0.0087 (9) | 0.0384 (11) |
O4 | 0.0724 (13) | 0.0648 (12) | 0.0582 (12) | 0.0184 (10) | −0.0061 (10) | 0.0272 (10) |
N1 | 0.0461 (11) | 0.0337 (10) | 0.0448 (12) | 0.0153 (9) | 0.0068 (9) | 0.0090 (9) |
C1 | 0.0513 (15) | 0.0443 (14) | 0.0428 (14) | 0.0203 (12) | 0.0006 (12) | 0.0005 (12) |
C2 | 0.0531 (14) | 0.0325 (12) | 0.0371 (13) | 0.0142 (11) | −0.0064 (11) | 0.0000 (11) |
C3 | 0.0696 (17) | 0.0413 (15) | 0.0537 (17) | 0.0255 (14) | −0.0121 (14) | −0.0024 (13) |
C4 | 0.091 (2) | 0.0343 (14) | 0.0571 (18) | 0.0172 (15) | −0.0162 (16) | 0.0082 (13) |
C5 | 0.0782 (19) | 0.0406 (15) | 0.0549 (17) | 0.0065 (14) | 0.0017 (15) | 0.0119 (13) |
C6 | 0.0594 (16) | 0.0390 (14) | 0.0590 (17) | 0.0097 (13) | 0.0101 (13) | 0.0101 (13) |
C7 | 0.0467 (14) | 0.0332 (12) | 0.0418 (14) | 0.0103 (11) | −0.0008 (11) | 0.0035 (11) |
C8 | 0.0423 (13) | 0.0384 (13) | 0.0418 (14) | 0.0142 (11) | 0.0019 (11) | 0.0059 (11) |
C9 | 0.0431 (14) | 0.0369 (13) | 0.0354 (13) | 0.0140 (11) | 0.0054 (10) | 0.0071 (10) |
C10 | 0.0366 (13) | 0.0461 (14) | 0.0452 (14) | 0.0123 (11) | 0.0012 (11) | 0.0086 (12) |
C11 | 0.0451 (14) | 0.0497 (15) | 0.0404 (14) | 0.0201 (12) | −0.0006 (11) | 0.0097 (12) |
C12 | 0.0435 (14) | 0.0398 (13) | 0.0341 (13) | 0.0164 (11) | 0.0058 (10) | 0.0078 (10) |
C13 | 0.0362 (13) | 0.0492 (15) | 0.0488 (15) | 0.0112 (11) | 0.0015 (11) | 0.0113 (12) |
C14 | 0.0459 (15) | 0.0511 (15) | 0.0435 (15) | 0.0165 (12) | −0.0021 (11) | 0.0150 (12) |
C15 | 0.0524 (16) | 0.0481 (15) | 0.0418 (15) | 0.0188 (13) | 0.0068 (12) | 0.0091 (12) |
O5 | 0.0546 (12) | 0.0571 (11) | 0.0726 (13) | 0.0127 (9) | 0.0127 (10) | 0.0232 (10) |
N2 | 0.0400 (12) | 0.0579 (13) | 0.0520 (13) | 0.0168 (10) | 0.0056 (10) | 0.0148 (11) |
C16 | 0.0627 (18) | 0.0513 (16) | 0.0480 (16) | 0.0256 (14) | 0.0049 (13) | 0.0122 (13) |
C17 | 0.0469 (17) | 0.136 (3) | 0.087 (2) | 0.0364 (19) | 0.0104 (16) | 0.019 (2) |
C18 | 0.0640 (17) | 0.0617 (17) | 0.0614 (17) | 0.0216 (14) | 0.0094 (14) | 0.0246 (14) |
Geometric parameters (Å, º) top
O1—C1 | 1.202 (3) | C9—C10 | 1.387 (3) |
O2—C8 | 1.208 (3) | C10—C11 | 1.376 (3) |
O3—C15 | 1.313 (3) | C10—H10 | 0.9300 |
O3—H3 | 0.8200 | C11—C12 | 1.382 (3) |
O4—C15 | 1.208 (3) | C11—H11 | 0.9300 |
N1—C8 | 1.402 (3) | C12—C13 | 1.387 (3) |
N1—C1 | 1.413 (3) | C12—C15 | 1.492 (3) |
N1—C9 | 1.433 (3) | C13—C14 | 1.375 (3) |
C1—C2 | 1.482 (3) | C13—H13 | 0.9300 |
C2—C7 | 1.377 (3) | C14—H14 | 0.9300 |
C2—C3 | 1.384 (3) | O5—C16 | 1.234 (3) |
C3—C4 | 1.381 (4) | N2—C16 | 1.311 (3) |
C3—H3A | 0.9300 | N2—C18 | 1.447 (3) |
C4—C5 | 1.371 (4) | N2—C17 | 1.451 (3) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.384 (3) | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C6—C7 | 1.384 (3) | C17—H17C | 0.9600 |
C6—H6 | 0.9300 | C18—H18A | 0.9600 |
C7—C8 | 1.481 (3) | C18—H18B | 0.9600 |
C9—C14 | 1.379 (3) | C18—H18C | 0.9600 |
| | | |
C15—O3—H3 | 109.5 | C10—C11—C12 | 121.1 (2) |
C8—N1—C1 | 111.49 (18) | C10—C11—H11 | 119.5 |
C8—N1—C9 | 125.41 (18) | C12—C11—H11 | 119.5 |
C1—N1—C9 | 123.00 (18) | C11—C12—C13 | 118.9 (2) |
O1—C1—N1 | 125.0 (2) | C11—C12—C15 | 119.7 (2) |
O1—C1—C2 | 129.3 (2) | C13—C12—C15 | 121.4 (2) |
N1—C1—C2 | 105.62 (19) | C14—C13—C12 | 120.6 (2) |
C7—C2—C3 | 121.6 (2) | C14—C13—H13 | 119.7 |
C7—C2—C1 | 108.30 (19) | C12—C13—H13 | 119.7 |
C3—C2—C1 | 130.1 (2) | C13—C14—C9 | 119.7 (2) |
C4—C3—C2 | 117.2 (2) | C13—C14—H14 | 120.1 |
C4—C3—H3A | 121.4 | C9—C14—H14 | 120.1 |
C2—C3—H3A | 121.4 | O4—C15—O3 | 123.7 (2) |
C5—C4—C3 | 121.5 (2) | O4—C15—C12 | 122.9 (2) |
C5—C4—H4 | 119.2 | O3—C15—C12 | 113.3 (2) |
C3—C4—H4 | 119.2 | C16—N2—C18 | 121.3 (2) |
C4—C5—C6 | 121.3 (3) | C16—N2—C17 | 121.2 (2) |
C4—C5—H5 | 119.4 | C18—N2—C17 | 117.5 (2) |
C6—C5—H5 | 119.4 | O5—C16—N2 | 124.5 (2) |
C5—C6—C7 | 117.6 (2) | O5—C16—H16 | 117.7 |
C5—C6—H6 | 121.2 | N2—C16—H16 | 117.7 |
C7—C6—H6 | 121.2 | N2—C17—H17A | 109.5 |
C2—C7—C6 | 120.8 (2) | N2—C17—H17B | 109.5 |
C2—C7—C8 | 109.07 (19) | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 130.0 (2) | N2—C17—H17C | 109.5 |
O2—C8—N1 | 125.0 (2) | H17A—C17—H17C | 109.5 |
O2—C8—C7 | 129.4 (2) | H17B—C17—H17C | 109.5 |
N1—C8—C7 | 105.51 (19) | N2—C18—H18A | 109.5 |
C14—C9—C10 | 120.5 (2) | N2—C18—H18B | 109.5 |
C14—C9—N1 | 118.84 (19) | H18A—C18—H18B | 109.5 |
C10—C9—N1 | 120.7 (2) | N2—C18—H18C | 109.5 |
C11—C10—C9 | 119.2 (2) | H18A—C18—H18C | 109.5 |
C11—C10—H10 | 120.4 | H18B—C18—H18C | 109.5 |
C9—C10—H10 | 120.4 | | |
| | | |
C8—N1—C1—O1 | 179.2 (2) | C6—C7—C8—O2 | 0.6 (4) |
C9—N1—C1—O1 | −4.1 (4) | C2—C7—C8—N1 | 0.8 (3) |
C8—N1—C1—C2 | −0.8 (2) | C6—C7—C8—N1 | 178.1 (2) |
C9—N1—C1—C2 | 175.92 (19) | C8—N1—C9—C14 | 125.6 (2) |
O1—C1—C2—C7 | −178.7 (3) | C1—N1—C9—C14 | −50.6 (3) |
N1—C1—C2—C7 | 1.3 (3) | C8—N1—C9—C10 | −56.5 (3) |
O1—C1—C2—C3 | 2.4 (4) | C1—N1—C9—C10 | 127.3 (2) |
N1—C1—C2—C3 | −177.6 (2) | C14—C9—C10—C11 | 1.7 (3) |
C7—C2—C3—C4 | −0.1 (4) | N1—C9—C10—C11 | −176.1 (2) |
C1—C2—C3—C4 | 178.6 (2) | C9—C10—C11—C12 | −0.2 (3) |
C2—C3—C4—C5 | −0.6 (4) | C10—C11—C12—C13 | −1.5 (3) |
C3—C4—C5—C6 | 1.4 (4) | C10—C11—C12—C15 | 176.4 (2) |
C4—C5—C6—C7 | −1.3 (4) | C11—C12—C13—C14 | 1.5 (3) |
C3—C2—C7—C6 | 0.1 (4) | C15—C12—C13—C14 | −176.2 (2) |
C1—C2—C7—C6 | −178.8 (2) | C12—C13—C14—C9 | 0.0 (3) |
C3—C2—C7—C8 | 177.7 (2) | C10—C9—C14—C13 | −1.7 (3) |
C1—C2—C7—C8 | −1.3 (3) | N1—C9—C14—C13 | 176.2 (2) |
C5—C6—C7—C2 | 0.6 (4) | C11—C12—C15—O4 | −7.5 (4) |
C5—C6—C7—C8 | −176.4 (2) | C13—C12—C15—O4 | 170.3 (2) |
C1—N1—C8—O2 | 177.7 (2) | C11—C12—C15—O3 | 175.0 (2) |
C9—N1—C8—O2 | 1.1 (4) | C13—C12—C15—O3 | −7.2 (3) |
C1—N1—C8—C7 | 0.0 (2) | C18—N2—C16—O5 | −1.7 (4) |
C9—N1—C8—C7 | −176.55 (19) | C17—N2—C16—O5 | −179.0 (2) |
C2—C7—C8—O2 | −176.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O5i | 0.82 | 1.76 | 2.573 (3) | 169 |
C17—H17A···O5ii | 0.96 | 2.52 | 3.269 (4) | 135 |
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z. |