The title molecule adopts an
s-
cis configuration with respect to the C=O and C=C bonds. The dihedral angle between the indole ring system and the nitro-substituted benzene ring is 37.64 (16)°. In the crystal, molecules are linked by O—-H

O and N—H

O hydrogen bonds, forming chains along [010]. In addition, weak C—H

O, C—H

π and π–π interactions further link the structure into a three-dimensional network.
Supporting information
CCDC reference: 1846181
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.061
- wR factor = 0.190
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.12
Rint given 0.129
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full ! Check
PLAT031_ALERT_4_C Refined Extinction Parameter Within Range ...... 2.500 Sigma
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C1 -C6 1.36 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C12 -C17 1.35 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00539 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -2.941 Report
Alert level G
PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 ......... 0.129 Report
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.83 mm
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT960_ALERT_3_G Number of Intensities with I < - 2*sig(I) ... 4 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2009) and Mercury (Macrae et al.,
2008); software used to prepare material for publication: PLATON (Spek, 2009).
(
E)-3-(1
H-indol-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one
hemihydrate
top
Crystal data top
2C17H12N2O3·H2O | F(000) = 1256 |
Mr = 602.59 | Dx = 1.496 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.835 (7) Å | Cell parameters from 1566 reflections |
b = 6.453 (2) Å | θ = 2.9–19.5° |
c = 28.000 (11) Å | µ = 0.11 mm−1 |
β = 93.505 (10)° | T = 296 K |
V = 2675.4 (18) Å3 | Plate, orange |
Z = 4 | 0.83 × 0.31 × 0.04 mm |
Data collection top
Bruker APEXII CCD diffractometer | 1263 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.129 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 25.0°, θmin = 2.8° |
Tmin = 0.638, Tmax = 0.955 | h = −17→17 |
36005 measured reflections | k = −7→7 |
2369 independent reflections | l = −33→33 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.0548P)2 + 3.4801P]
where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.190 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.22 e Å−3 |
2369 reflections | Δρmin = −0.19 e Å−3 |
213 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0010 (4) |
Special details top
Experimental. The following wavelength and cell were deduced by SADABS from the
direction cosines etc. They are given here for emergency use only:
CELL 0.71150 6.604 8.276 28.665 93.349 89.966 113.537 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.8500 (2) | 0.5670 (5) | 0.21045 (11) | 0.0608 (8) | |
H1A | 0.892 (2) | 0.494 (6) | 0.2257 (13) | 0.071 (12)* | |
N2 | 1.1251 (3) | 0.4606 (7) | 0.48886 (12) | 0.0826 (11) | |
O1 | 0.98111 (17) | 1.0824 (4) | 0.33010 (9) | 0.0713 (8) | |
O2 | 1.1071 (3) | 0.2810 (6) | 0.49214 (12) | 0.1143 (13) | |
O3 | 1.1754 (2) | 0.5484 (6) | 0.51669 (11) | 0.1137 (12) | |
C1 | 0.8028 (2) | 0.5110 (6) | 0.16995 (12) | 0.0579 (9) | |
C2 | 0.8031 (3) | 0.3301 (6) | 0.14546 (14) | 0.0712 (11) | |
H2A | 0.8396 | 0.2200 | 0.1559 | 0.085* | |
C3 | 0.7485 (3) | 0.3159 (7) | 0.10529 (15) | 0.0802 (12) | |
H3A | 0.7470 | 0.1935 | 0.0877 | 0.096* | |
C4 | 0.6954 (3) | 0.4782 (8) | 0.09007 (15) | 0.0802 (12) | |
H4A | 0.6584 | 0.4637 | 0.0622 | 0.096* | |
C5 | 0.6950 (3) | 0.6569 (7) | 0.11385 (14) | 0.0750 (12) | |
H5A | 0.6590 | 0.7666 | 0.1025 | 0.090* | |
C6 | 0.7487 (2) | 0.6766 (6) | 0.15553 (13) | 0.0620 (10) | |
C7 | 0.7659 (2) | 0.8323 (6) | 0.18888 (13) | 0.0613 (10) | |
H7A | 0.7388 | 0.9623 | 0.1884 | 0.074* | |
C8 | 0.8281 (2) | 0.7644 (6) | 0.22200 (12) | 0.0569 (9) | |
C9 | 0.8692 (2) | 0.8667 (6) | 0.26162 (12) | 0.0586 (10) | |
H9A | 0.8545 | 1.0055 | 0.2656 | 0.070* | |
C10 | 0.9266 (2) | 0.7848 (6) | 0.29370 (12) | 0.0603 (10) | |
H10A | 0.9386 | 0.6439 | 0.2913 | 0.072* | |
C11 | 0.9717 (2) | 0.8965 (6) | 0.33203 (12) | 0.0574 (9) | |
C12 | 1.0089 (2) | 0.7823 (5) | 0.37368 (12) | 0.0560 (9) | |
C13 | 0.9864 (3) | 0.5825 (6) | 0.38163 (13) | 0.0678 (11) | |
H13A | 0.9450 | 0.5162 | 0.3605 | 0.081* | |
C14 | 1.0231 (3) | 0.4790 (6) | 0.41952 (13) | 0.0694 (11) | |
H14A | 1.0072 | 0.3421 | 0.4249 | 0.083* | |
C15 | 1.0831 (2) | 0.5757 (6) | 0.44943 (12) | 0.0634 (10) | |
C16 | 1.1064 (3) | 0.7740 (7) | 0.44334 (14) | 0.0729 (11) | |
H16A | 1.1475 | 0.8391 | 0.4648 | 0.088* | |
C17 | 1.0683 (3) | 0.8770 (6) | 0.40510 (13) | 0.0668 (11) | |
H17A | 1.0832 | 1.0152 | 0.4004 | 0.080* | |
O1W | 1.0000 | 0.3138 (6) | 0.2500 | 0.0710 (11) | |
H1OW | 1.012 (3) | 0.237 (6) | 0.2254 (14) | 0.094 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.061 (2) | 0.063 (2) | 0.0561 (19) | 0.0041 (17) | −0.0096 (16) | 0.0024 (16) |
N2 | 0.090 (3) | 0.093 (3) | 0.063 (2) | 0.004 (2) | −0.010 (2) | 0.008 (2) |
O1 | 0.0864 (19) | 0.0584 (17) | 0.0674 (17) | −0.0039 (14) | −0.0090 (14) | 0.0005 (13) |
O2 | 0.153 (3) | 0.089 (2) | 0.096 (2) | −0.002 (2) | −0.032 (2) | 0.025 (2) |
O3 | 0.128 (3) | 0.128 (3) | 0.079 (2) | −0.006 (2) | −0.043 (2) | 0.007 (2) |
C1 | 0.056 (2) | 0.064 (2) | 0.053 (2) | −0.0047 (18) | −0.0023 (17) | 0.0009 (19) |
C2 | 0.079 (3) | 0.064 (3) | 0.069 (3) | −0.002 (2) | −0.001 (2) | −0.008 (2) |
C3 | 0.081 (3) | 0.084 (3) | 0.076 (3) | −0.014 (3) | 0.006 (2) | −0.018 (2) |
C4 | 0.065 (3) | 0.106 (3) | 0.068 (3) | −0.011 (3) | −0.008 (2) | −0.015 (3) |
C5 | 0.067 (3) | 0.087 (3) | 0.069 (3) | 0.004 (2) | −0.014 (2) | −0.003 (2) |
C6 | 0.057 (2) | 0.067 (2) | 0.060 (2) | −0.004 (2) | −0.0039 (18) | 0.002 (2) |
C7 | 0.061 (2) | 0.056 (2) | 0.066 (2) | 0.0046 (18) | −0.0078 (19) | 0.005 (2) |
C8 | 0.057 (2) | 0.056 (2) | 0.057 (2) | −0.0013 (18) | −0.0010 (18) | −0.0047 (18) |
C9 | 0.057 (2) | 0.060 (2) | 0.058 (2) | −0.0015 (17) | −0.0025 (18) | −0.0025 (18) |
C10 | 0.065 (2) | 0.056 (2) | 0.059 (2) | 0.0033 (18) | −0.0023 (19) | −0.0037 (19) |
C11 | 0.055 (2) | 0.058 (2) | 0.058 (2) | 0.0012 (18) | −0.0013 (18) | −0.0020 (19) |
C12 | 0.056 (2) | 0.055 (2) | 0.056 (2) | 0.0008 (18) | −0.0019 (18) | −0.0055 (18) |
C13 | 0.072 (3) | 0.065 (2) | 0.064 (2) | −0.008 (2) | −0.015 (2) | 0.002 (2) |
C14 | 0.077 (3) | 0.065 (3) | 0.064 (2) | −0.006 (2) | −0.006 (2) | 0.002 (2) |
C15 | 0.068 (2) | 0.070 (3) | 0.051 (2) | 0.004 (2) | −0.0066 (19) | 0.000 (2) |
C16 | 0.079 (3) | 0.076 (3) | 0.062 (2) | −0.010 (2) | −0.012 (2) | −0.007 (2) |
C17 | 0.072 (2) | 0.064 (2) | 0.063 (2) | −0.008 (2) | −0.010 (2) | −0.005 (2) |
O1W | 0.091 (3) | 0.055 (2) | 0.065 (3) | 0.000 | −0.012 (2) | 0.000 |
Geometric parameters (Å, º) top
N1—C1 | 1.345 (4) | C7—H7A | 0.9300 |
N1—C8 | 1.359 (4) | C8—C9 | 1.399 (5) |
N1—H1A | 0.87 (4) | C9—C10 | 1.310 (5) |
N2—O3 | 1.189 (4) | C9—H9A | 0.9300 |
N2—O2 | 1.194 (4) | C10—C11 | 1.426 (5) |
N2—C15 | 1.440 (5) | C10—H10A | 0.9300 |
O1—C11 | 1.209 (4) | C11—C12 | 1.459 (5) |
C1—C2 | 1.354 (5) | C12—C17 | 1.353 (5) |
C1—C6 | 1.382 (5) | C12—C13 | 1.353 (5) |
C2—C3 | 1.348 (5) | C13—C14 | 1.341 (5) |
C2—H2A | 0.9300 | C13—H13A | 0.9300 |
C3—C4 | 1.363 (6) | C14—C15 | 1.338 (5) |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—C5 | 1.332 (5) | C15—C16 | 1.339 (5) |
C4—H4A | 0.9300 | C16—C17 | 1.354 (5) |
C5—C6 | 1.378 (5) | C16—H16A | 0.9300 |
C5—H5A | 0.9300 | C17—H17A | 0.9300 |
C6—C7 | 1.385 (5) | O1W—H1OW | 0.88 (4) |
C7—C8 | 1.341 (4) | | |
| | | |
C1—N1—C8 | 109.4 (3) | N1—C8—C9 | 122.2 (3) |
C1—N1—H1A | 126 (2) | C10—C9—C8 | 126.0 (4) |
C8—N1—H1A | 124 (2) | C10—C9—H9A | 117.0 |
O3—N2—O2 | 123.1 (4) | C8—C9—H9A | 117.0 |
O3—N2—C15 | 118.8 (4) | C9—C10—C11 | 124.6 (3) |
O2—N2—C15 | 118.1 (4) | C9—C10—H10A | 117.7 |
N1—C1—C2 | 129.9 (4) | C11—C10—H10A | 117.7 |
N1—C1—C6 | 107.6 (3) | O1—C11—C10 | 121.2 (3) |
C2—C1—C6 | 122.6 (3) | O1—C11—C12 | 119.9 (3) |
C3—C2—C1 | 117.4 (4) | C10—C11—C12 | 118.9 (3) |
C3—C2—H2A | 121.3 | C17—C12—C13 | 118.7 (4) |
C1—C2—H2A | 121.3 | C17—C12—C11 | 119.4 (3) |
C2—C3—C4 | 121.0 (4) | C13—C12—C11 | 121.9 (3) |
C2—C3—H3A | 119.5 | C14—C13—C12 | 120.8 (4) |
C4—C3—H3A | 119.5 | C14—C13—H13A | 119.6 |
C5—C4—C3 | 122.0 (4) | C12—C13—H13A | 119.6 |
C5—C4—H4A | 119.0 | C15—C14—C13 | 119.0 (4) |
C3—C4—H4A | 119.0 | C15—C14—H14A | 120.5 |
C4—C5—C6 | 118.9 (4) | C13—C14—H14A | 120.5 |
C4—C5—H5A | 120.6 | C14—C15—C16 | 122.2 (4) |
C6—C5—H5A | 120.6 | C14—C15—N2 | 118.6 (4) |
C5—C6—C1 | 118.1 (4) | C16—C15—N2 | 119.2 (4) |
C5—C6—C7 | 135.3 (4) | C15—C16—C17 | 118.2 (4) |
C1—C6—C7 | 106.5 (3) | C15—C16—H16A | 120.9 |
C8—C7—C6 | 108.6 (3) | C17—C16—H16A | 120.9 |
C8—C7—H7A | 125.7 | C12—C17—C16 | 121.0 (4) |
C6—C7—H7A | 125.7 | C12—C17—H17A | 119.5 |
C7—C8—N1 | 107.8 (3) | C16—C17—H17A | 119.5 |
C7—C8—C9 | 130.0 (4) | | |
| | | |
C8—N1—C1—C2 | 179.9 (4) | C8—C9—C10—C11 | 175.8 (3) |
C8—N1—C1—C6 | −0.6 (4) | C9—C10—C11—O1 | −21.9 (6) |
N1—C1—C2—C3 | −179.9 (4) | C9—C10—C11—C12 | 159.5 (4) |
C6—C1—C2—C3 | 0.6 (6) | O1—C11—C12—C17 | −13.1 (5) |
C1—C2—C3—C4 | 0.2 (6) | C10—C11—C12—C17 | 165.5 (3) |
C2—C3—C4—C5 | 0.0 (7) | O1—C11—C12—C13 | 167.7 (4) |
C3—C4—C5—C6 | −1.2 (6) | C10—C11—C12—C13 | −13.7 (5) |
C4—C5—C6—C1 | 1.9 (6) | C17—C12—C13—C14 | −0.9 (6) |
C4—C5—C6—C7 | 179.8 (4) | C11—C12—C13—C14 | 178.3 (4) |
N1—C1—C6—C5 | 178.7 (3) | C12—C13—C14—C15 | −0.4 (6) |
C2—C1—C6—C5 | −1.7 (6) | C13—C14—C15—C16 | 1.3 (6) |
N1—C1—C6—C7 | 0.2 (4) | C13—C14—C15—N2 | −177.3 (4) |
C2—C1—C6—C7 | 179.8 (3) | O3—N2—C15—C14 | −176.8 (4) |
C5—C6—C7—C8 | −177.8 (4) | O2—N2—C15—C14 | 2.8 (6) |
C1—C6—C7—C8 | 0.3 (4) | O3—N2—C15—C16 | 4.5 (6) |
C6—C7—C8—N1 | −0.6 (4) | O2—N2—C15—C16 | −176.0 (4) |
C6—C7—C8—C9 | 177.6 (4) | C14—C15—C16—C17 | −0.9 (6) |
C1—N1—C8—C7 | 0.7 (4) | N2—C15—C16—C17 | 177.8 (4) |
C1—N1—C8—C9 | −177.7 (3) | C13—C12—C17—C16 | 1.4 (6) |
C7—C8—C9—C10 | 176.4 (4) | C11—C12—C17—C16 | −177.9 (4) |
N1—C8—C9—C10 | −5.5 (6) | C15—C16—C17—C12 | −0.5 (6) |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the N1/C1/C6–C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1OW···O1i | 0.88 (4) | 1.86 (4) | 2.723 (4) | 171 (4) |
N1—H1A···O1W | 0.87 (3) | 2.06 (3) | 2.923 (4) | 170 (3) |
C4—H4A···O2ii | 0.93 | 2.60 | 3.405 (6) | 146 |
C9—H9A···Cg1iii | 0.93 | 2.87 | 3.518 (4) | 127 |
Symmetry codes: (i) −x+2, y−1, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2. |