The title compound, C
20H
19N
3O
4·H
2O, has been synthesized by the reaction of 2-(2-formylphenoxy)acetic acid with 4-aminoantipyrine in ethanol. It comprises a 4-aminoantipyrine Schiff base and a water molecule. The dihedral angles made by the pyrazoline ring with the substituted and unsubstituted phenyl rings are 14.8 (2) and 58.1 (2)°, respectively. In the crystal structure, the molecules are held together by intermolecular O—H
O hydrogen bonds and weak C—H
O, intermolecular hydrogen bonds, as well as π–π stacking interactions.
Supporting information
CCDC reference: 618969
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.126
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C1 .. 5.47 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2; software used to prepare material for publication: APEX2.
{(
E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1
H-pyrazol-4-
yliminomethyl)phenoxy]acetic acid monohydrate
top
Crystal data top
C20H19N3O4·H2O | F(000) = 1616 |
Mr = 383.40 | Dx = 1.359 Mg m−3 |
Monoclinic, C2/c | Melting point = 466.2–466.9 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.0213 (15) Å | Cell parameters from 1657 reflections |
b = 6.8755 (6) Å | θ = 2.3–25.0° |
c = 30.352 (3) Å | µ = 0.10 mm−1 |
β = 94.518 (2)° | T = 296 K |
V = 3749.1 (6) Å3 | Block, yellow |
Z = 8 | 0.20 × 0.14 × 0.08 mm |
Data collection top
Bruker APEX-II area-detector diffractometer | 3231 independent reflections |
Radiation source: fine-focus sealed tube | 1522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −21→21 |
Tmin = 0.98, Tmax = 0.99 | k = −8→7 |
10093 measured reflections | l = −36→34 |
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)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0499P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3231 reflections | Δρmax = 0.18 e Å−3 |
265 parameters | Δρmin = −0.18 e Å−3 |
3 restraints | Extinction correction: APEX2, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0009 (2) |
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 | −0.00791 (11) | 0.6046 (3) | 0.87063 (7) | 0.0610 (6) | |
O2 | 0.18056 (11) | 0.8674 (3) | 0.94052 (7) | 0.0574 (6) | |
O3 | 0.05648 (12) | 1.0462 (4) | 0.95971 (8) | 0.0841 (8) | |
O4 | 0.12074 (13) | 1.2879 (4) | 0.99355 (9) | 0.0860 (8) | |
H4A | 0.0792 | 1.3259 | 0.9987 | 0.129* | |
O5 | 0.00245 (16) | 0.6615 (5) | 0.96328 (10) | 0.0902 (8) | |
N1 | −0.05004 (12) | 0.3334 (3) | 0.83101 (8) | 0.0489 (7) | |
N2 | −0.01738 (13) | 0.1641 (4) | 0.81545 (8) | 0.0492 (6) | |
N3 | 0.14185 (12) | 0.3618 (4) | 0.87651 (7) | 0.0487 (6) | |
C1 | 0.15482 (16) | 0.5224 (5) | 0.89700 (9) | 0.0497 (8) | |
H1 | 0.1150 | 0.6028 | 0.9024 | 0.060* | |
C2 | 0.23058 (15) | 0.5836 (4) | 0.91218 (9) | 0.0449 (8) | |
C3 | 0.24315 (16) | 0.7617 (5) | 0.93360 (9) | 0.0492 (8) | |
C4 | 0.31477 (17) | 0.8228 (5) | 0.94696 (10) | 0.0574 (9) | |
H4 | 0.3225 | 0.9411 | 0.9615 | 0.069* | |
C5 | 0.37456 (18) | 0.7064 (6) | 0.93853 (11) | 0.0668 (10) | |
H5 | 0.4227 | 0.7480 | 0.9469 | 0.080* | |
C6 | 0.36338 (17) | 0.5296 (5) | 0.91789 (10) | 0.0672 (10) | |
H6 | 0.4038 | 0.4507 | 0.9129 | 0.081* | |
C7 | 0.29245 (16) | 0.4699 (5) | 0.90473 (10) | 0.0591 (9) | |
H7 | 0.2854 | 0.3508 | 0.8905 | 0.071* | |
C8 | 0.18960 (16) | 1.0448 (4) | 0.96428 (9) | 0.0531 (8) | |
H8A | 0.2168 | 1.1374 | 0.9476 | 0.064* | |
H8B | 0.2176 | 1.0223 | 0.9924 | 0.064* | |
C9 | 0.11482 (19) | 1.1230 (5) | 0.97158 (11) | 0.0601 (9) | |
C10 | 0.00416 (16) | 0.4392 (5) | 0.85674 (9) | 0.0479 (8) | |
C11 | 0.06979 (16) | 0.3183 (4) | 0.85914 (9) | 0.0437 (8) | |
C12 | 0.05254 (16) | 0.1511 (4) | 0.83597 (9) | 0.0465 (8) | |
C13 | 0.09902 (16) | −0.0241 (4) | 0.83191 (10) | 0.0640 (9) | |
H13A | 0.1462 | −0.0057 | 0.8484 | 0.096* | |
H13B | 0.1068 | −0.0456 | 0.8014 | 0.096* | |
H13C | 0.0743 | −0.1347 | 0.8433 | 0.096* | |
C14 | −0.06675 (17) | −0.0012 (4) | 0.80614 (10) | 0.0636 (9) | |
H14A | −0.0792 | −0.0584 | 0.8334 | 0.095* | |
H14B | −0.0422 | −0.0960 | 0.7892 | 0.095* | |
H14C | −0.1114 | 0.0420 | 0.7897 | 0.095* | |
C15 | −0.10746 (15) | 0.4290 (4) | 0.80384 (9) | 0.0440 (8) | |
C16 | −0.10647 (15) | 0.4333 (4) | 0.75853 (10) | 0.0492 (8) | |
H16 | −0.0699 | 0.3658 | 0.7448 | 0.059* | |
C17 | −0.16005 (16) | 0.5383 (5) | 0.73342 (10) | 0.0560 (9) | |
H17 | −0.1601 | 0.5393 | 0.7028 | 0.067* | |
C18 | −0.21312 (16) | 0.6412 (4) | 0.75379 (11) | 0.0562 (9) | |
H18 | −0.2483 | 0.7148 | 0.7370 | 0.067* | |
C19 | −0.21403 (16) | 0.6349 (4) | 0.79913 (11) | 0.0581 (9) | |
H19 | −0.2502 | 0.7037 | 0.8129 | 0.070* | |
C20 | −0.16193 (16) | 0.5276 (4) | 0.82428 (10) | 0.0551 (9) | |
H20 | −0.1634 | 0.5217 | 0.8548 | 0.066* | |
H5A | 0.023 (2) | 0.779 (3) | 0.9636 (12) | 0.106 (17)* | |
H5B | −0.004 (3) | 0.624 (7) | 0.9351 (9) | 0.25 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0587 (14) | 0.0502 (16) | 0.0713 (15) | 0.0059 (12) | −0.0131 (11) | −0.0163 (12) |
O2 | 0.0520 (13) | 0.0486 (15) | 0.0696 (14) | 0.0000 (11) | −0.0079 (10) | −0.0162 (11) |
O3 | 0.0553 (15) | 0.087 (2) | 0.108 (2) | −0.0058 (14) | −0.0044 (13) | −0.0360 (15) |
O4 | 0.0727 (17) | 0.078 (2) | 0.107 (2) | 0.0003 (14) | 0.0019 (16) | −0.0411 (16) |
O5 | 0.095 (2) | 0.090 (3) | 0.086 (2) | −0.0152 (18) | 0.0091 (15) | −0.0088 (17) |
N1 | 0.0478 (15) | 0.0405 (17) | 0.0564 (16) | 0.0014 (13) | −0.0091 (12) | −0.0090 (13) |
N2 | 0.0508 (16) | 0.0374 (17) | 0.0581 (16) | −0.0038 (13) | −0.0048 (12) | −0.0050 (12) |
N3 | 0.0510 (16) | 0.0434 (17) | 0.0497 (15) | −0.0025 (13) | −0.0082 (12) | −0.0025 (13) |
C1 | 0.0458 (18) | 0.053 (2) | 0.0496 (19) | 0.0033 (16) | −0.0023 (14) | 0.0029 (16) |
C2 | 0.0480 (19) | 0.048 (2) | 0.0379 (17) | −0.0027 (16) | −0.0024 (13) | −0.0020 (15) |
C3 | 0.045 (2) | 0.055 (2) | 0.0472 (19) | 0.0031 (17) | −0.0007 (15) | 0.0030 (16) |
C4 | 0.049 (2) | 0.062 (2) | 0.059 (2) | −0.0068 (18) | −0.0077 (16) | −0.0088 (17) |
C5 | 0.044 (2) | 0.085 (3) | 0.071 (2) | −0.008 (2) | −0.0032 (17) | −0.002 (2) |
C6 | 0.048 (2) | 0.081 (3) | 0.072 (2) | 0.009 (2) | 0.0012 (17) | −0.005 (2) |
C7 | 0.054 (2) | 0.065 (3) | 0.056 (2) | 0.0067 (19) | −0.0042 (16) | −0.0085 (17) |
C8 | 0.0546 (19) | 0.046 (2) | 0.057 (2) | −0.0042 (16) | −0.0030 (15) | −0.0060 (16) |
C9 | 0.060 (2) | 0.060 (3) | 0.060 (2) | −0.001 (2) | 0.0018 (17) | −0.0109 (19) |
C10 | 0.053 (2) | 0.041 (2) | 0.0483 (19) | −0.0044 (17) | −0.0066 (14) | 0.0008 (16) |
C11 | 0.0490 (19) | 0.038 (2) | 0.0428 (17) | −0.0013 (15) | −0.0047 (14) | 0.0026 (14) |
C12 | 0.0474 (19) | 0.042 (2) | 0.0483 (18) | −0.0002 (16) | −0.0048 (14) | 0.0050 (15) |
C13 | 0.069 (2) | 0.046 (2) | 0.075 (2) | 0.0089 (18) | −0.0070 (17) | −0.0029 (17) |
C14 | 0.065 (2) | 0.046 (2) | 0.078 (2) | −0.0138 (18) | −0.0036 (17) | −0.0039 (18) |
C15 | 0.0394 (17) | 0.041 (2) | 0.051 (2) | −0.0054 (15) | −0.0040 (14) | −0.0057 (15) |
C16 | 0.0422 (18) | 0.053 (2) | 0.052 (2) | 0.0021 (15) | 0.0044 (14) | −0.0056 (16) |
C17 | 0.055 (2) | 0.061 (2) | 0.0515 (19) | −0.0019 (18) | −0.0017 (16) | 0.0021 (17) |
C18 | 0.0464 (19) | 0.050 (2) | 0.070 (3) | 0.0074 (17) | −0.0091 (17) | 0.0010 (17) |
C19 | 0.049 (2) | 0.058 (2) | 0.067 (2) | 0.0062 (17) | 0.0010 (16) | −0.0097 (18) |
C20 | 0.0510 (19) | 0.058 (2) | 0.056 (2) | 0.0003 (18) | 0.0009 (16) | −0.0033 (17) |
Geometric parameters (Å, º) top
O1—C10 | 1.238 (3) | C6—H6 | 0.9300 |
O2—C3 | 1.372 (3) | C7—H7 | 0.9300 |
O2—C8 | 1.420 (3) | C8—C9 | 1.484 (4) |
O3—C9 | 1.206 (4) | C8—H8A | 0.9700 |
O4—C9 | 1.315 (4) | C8—H8B | 0.9700 |
O4—H4A | 0.8200 | C10—C11 | 1.443 (4) |
O5—H5A | 0.883 (18) | C11—C12 | 1.370 (4) |
O5—H5B | 0.892 (19) | C12—C13 | 1.478 (4) |
N1—N2 | 1.403 (3) | C13—H13A | 0.9600 |
N1—C10 | 1.405 (3) | C13—H13B | 0.9600 |
N1—C15 | 1.432 (3) | C13—H13C | 0.9600 |
N2—C12 | 1.364 (3) | C14—H14A | 0.9600 |
N2—C14 | 1.457 (3) | C14—H14B | 0.9600 |
N3—C1 | 1.280 (3) | C14—H14C | 0.9600 |
N3—C11 | 1.395 (3) | C15—C16 | 1.377 (4) |
C1—C2 | 1.468 (4) | C15—C20 | 1.380 (4) |
C1—H1 | 0.9300 | C16—C17 | 1.385 (4) |
C2—C7 | 1.395 (4) | C16—H16 | 0.9300 |
C2—C3 | 1.396 (4) | C17—C18 | 1.375 (4) |
C3—C4 | 1.387 (4) | C17—H17 | 0.9300 |
C4—C5 | 1.382 (4) | C18—C19 | 1.378 (4) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.375 (4) | C19—C20 | 1.377 (4) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.372 (4) | C20—H20 | 0.9300 |
| | | |
C3—O2—C8 | 118.0 (2) | O1—C10—N1 | 122.1 (3) |
C9—O4—H4A | 109.5 | O1—C10—C11 | 132.6 (3) |
H5A—O5—H5B | 108 (3) | N1—C10—C11 | 105.1 (3) |
N2—N1—C10 | 109.0 (2) | C12—C11—N3 | 122.7 (3) |
N2—N1—C15 | 119.4 (2) | C12—C11—C10 | 107.8 (3) |
C10—N1—C15 | 121.4 (2) | N3—C11—C10 | 129.1 (3) |
C12—N2—N1 | 107.3 (2) | N2—C12—C11 | 110.1 (3) |
C12—N2—C14 | 124.5 (3) | N2—C12—C13 | 121.6 (3) |
N1—N2—C14 | 116.5 (2) | C11—C12—C13 | 128.3 (3) |
C1—N3—C11 | 119.9 (3) | C12—C13—H13A | 109.5 |
N3—C1—C2 | 122.0 (3) | C12—C13—H13B | 109.5 |
N3—C1—H1 | 119.0 | H13A—C13—H13B | 109.5 |
C2—C1—H1 | 119.0 | C12—C13—H13C | 109.5 |
C7—C2—C3 | 117.7 (3) | H13A—C13—H13C | 109.5 |
C7—C2—C1 | 121.6 (3) | H13B—C13—H13C | 109.5 |
C3—C2—C1 | 120.7 (3) | N2—C14—H14A | 109.5 |
O2—C3—C4 | 123.5 (3) | N2—C14—H14B | 109.5 |
O2—C3—C2 | 115.5 (3) | H14A—C14—H14B | 109.5 |
C4—C3—C2 | 121.0 (3) | N2—C14—H14C | 109.5 |
C5—C4—C3 | 119.4 (3) | H14A—C14—H14C | 109.5 |
C5—C4—H4 | 120.3 | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 120.3 | C16—C15—C20 | 120.3 (3) |
C6—C5—C4 | 120.5 (3) | C16—C15—N1 | 121.3 (3) |
C6—C5—H5 | 119.7 | C20—C15—N1 | 118.3 (3) |
C4—C5—H5 | 119.7 | C15—C16—C17 | 119.8 (3) |
C7—C6—C5 | 119.8 (3) | C15—C16—H16 | 120.1 |
C7—C6—H6 | 120.1 | C17—C16—H16 | 120.1 |
C5—C6—H6 | 120.1 | C18—C17—C16 | 120.0 (3) |
C6—C7—C2 | 121.6 (3) | C18—C17—H17 | 120.0 |
C6—C7—H7 | 119.2 | C16—C17—H17 | 120.0 |
C2—C7—H7 | 119.2 | C17—C18—C19 | 119.8 (3) |
O2—C8—C9 | 108.6 (3) | C17—C18—H18 | 120.1 |
O2—C8—H8A | 110.0 | C19—C18—H18 | 120.1 |
C9—C8—H8A | 110.0 | C20—C19—C18 | 120.6 (3) |
O2—C8—H8B | 110.0 | C20—C19—H19 | 119.7 |
C9—C8—H8B | 110.0 | C18—C19—H19 | 119.7 |
H8A—C8—H8B | 108.4 | C19—C20—C15 | 119.5 (3) |
O3—C9—O4 | 124.3 (3) | C19—C20—H20 | 120.3 |
O3—C9—C8 | 125.2 (3) | C15—C20—H20 | 120.3 |
O4—C9—C8 | 110.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5i | 0.82 | 1.94 | 2.688 (4) | 151 |
O5—H5B···O1 | 0.89 (2) | 1.96 (3) | 2.831 (4) | 166 (4) |
O5—H5A···O3 | 0.88 (2) | 1.95 (3) | 2.823 (4) | 173 (4) |
C4—H4···O4ii | 0.93 | 2.48 | 3.383 (4) | 163 |
C13—H13C···O1iii | 0.96 | 2.51 | 3.459 (4) | 172 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1/2, −y+5/2, −z+2; (iii) x, y−1, z. |