organic compounds
In the crystal structure of the title compound, C15H11NO4·H2O, there are hydrogen-bonded clusters involving conventional and unconventional hydrogen bonds of the types O—HO and C—HO. Pairs of molecules lie parallel to each other in a head-to-tail fashion, exhibiting strong π–π overlapping.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024329/ww2031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024329/ww2031Isup2.hkl |
CCDC reference: 618341
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.114
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.116 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 1855 Count of symmetry unique reflns 1879 Completeness (_total/calc) 98.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(Z)-3-(4-Nitrophenyl)-2-phenyl-2-propenoic acid monohydrate top
Crystal data top
C15H11NO4·H2O | F(000) = 600 |
Mr = 287.26 | Dx = 1.455 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 26803 reflections |
a = 7.578 (2) Å | θ = 3.5–28.3° |
b = 10.282 (2) Å | µ = 0.11 mm−1 |
c = 16.832 (4) Å | T = 173 K |
V = 1311.5 (5) Å3 | Prism, colorless |
Z = 4 | 0.18 × 0.15 × 0.12 mm |
Data collection top
Nonius KappaCCD diffractometer | 1855 independent reflections |
Radiation source: fine-focus sealed tube | 1280 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.116 |
ω and φ scans | θmax = 28.3°, θmin = 3.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −9→9 |
Tmin = 0.980, Tmax = 0.987 | k = −13→13 |
26803 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.248P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.002 |
S = 1.08 | Δρmax = 0.29 e Å−3 |
1855 reflections | Δρmin = −0.32 e Å−3 |
198 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.026 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: unk |
Secondary atom site location: difference Fourier map |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3298 (3) | 0.5086 (2) | 0.00396 (12) | 0.0348 (5) | |
O2 | 0.0644 (3) | 0.4546 (2) | −0.04433 (13) | 0.0338 (5) | |
H2 | 0.0944 | 0.3801 | −0.0290 | 0.051* | |
O3 | 0.1067 (3) | 0.6981 (2) | 0.36346 (13) | 0.0418 (6) | |
O4 | 0.1798 (3) | 0.9013 (2) | 0.35863 (13) | 0.0440 (6) | |
N1 | 0.1389 (3) | 0.7979 (3) | 0.32579 (15) | 0.0322 (6) | |
C1 | 0.1942 (4) | 0.5385 (3) | −0.02945 (16) | 0.0265 (6) | |
C2 | 0.1558 (4) | 0.6729 (3) | −0.06034 (16) | 0.0242 (6) | |
C3 | 0.1413 (4) | 0.7754 (3) | −0.01089 (17) | 0.0272 (6) | |
H3 | 0.1336 | 0.8579 | −0.0361 | 0.033* | |
C4 | 0.1358 (4) | 0.7783 (3) | 0.07563 (16) | 0.0251 (6) | |
C5 | 0.0641 (4) | 0.6773 (3) | 0.12139 (16) | 0.0257 (7) | |
H5 | 0.0158 | 0.6032 | 0.0956 | 0.031* | |
C6 | 0.0623 (4) | 0.6838 (3) | 0.20360 (17) | 0.0259 (7) | |
H6 | 0.0139 | 0.6150 | 0.2344 | 0.031* | |
C7 | 0.1327 (4) | 0.7929 (3) | 0.23976 (16) | 0.0255 (6) | |
C8 | 0.1991 (4) | 0.8969 (3) | 0.19692 (18) | 0.0284 (7) | |
H8 | 0.2440 | 0.9717 | 0.2231 | 0.034* | |
C9 | 0.1981 (4) | 0.8888 (3) | 0.11501 (17) | 0.0264 (7) | |
H9 | 0.2408 | 0.9601 | 0.0847 | 0.032* | |
C10 | 0.1455 (4) | 0.6883 (3) | −0.14787 (16) | 0.0243 (6) | |
C11 | 0.2193 (4) | 0.5976 (3) | −0.19887 (18) | 0.0250 (6) | |
H11 | 0.2755 | 0.5230 | −0.1772 | 0.030* | |
C12 | 0.2131 (4) | 0.6129 (3) | −0.28100 (18) | 0.0301 (7) | |
H12 | 0.2641 | 0.5491 | −0.3148 | 0.036* | |
C13 | 0.1314 (4) | 0.7223 (3) | −0.31343 (18) | 0.0315 (7) | |
H13 | 0.1280 | 0.7346 | −0.3693 | 0.038* | |
C14 | 0.0557 (4) | 0.8125 (3) | −0.26324 (18) | 0.0294 (7) | |
H14 | −0.0010 | 0.8868 | −0.2850 | 0.035* | |
C15 | 0.0611 (4) | 0.7966 (3) | −0.18190 (17) | 0.0273 (7) | |
H15 | 0.0072 | 0.8596 | −0.1485 | 0.033* | |
O5 | 0.1257 (3) | 0.20779 (19) | −0.00282 (14) | 0.0388 (6) | |
H51 | 0.1792 | 0.1621 | −0.0347 | 0.047* | |
H52 | 0.0401 | 0.1660 | 0.0125 | 0.047* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0319 (12) | 0.0304 (12) | 0.0421 (12) | 0.0031 (10) | −0.0128 (10) | 0.0007 (10) |
O2 | 0.0315 (11) | 0.0252 (11) | 0.0446 (13) | −0.0032 (9) | −0.0086 (10) | 0.0063 (10) |
O3 | 0.0585 (16) | 0.0366 (14) | 0.0303 (12) | 0.0063 (12) | 0.0058 (11) | 0.0039 (11) |
O4 | 0.0616 (16) | 0.0352 (12) | 0.0353 (12) | 0.0094 (13) | −0.0078 (13) | −0.0089 (11) |
N1 | 0.0346 (14) | 0.0307 (15) | 0.0314 (14) | 0.0097 (13) | 0.0006 (12) | −0.0038 (12) |
C1 | 0.0290 (16) | 0.0279 (15) | 0.0227 (14) | −0.0012 (13) | 0.0011 (13) | −0.0013 (13) |
C2 | 0.0198 (13) | 0.0254 (15) | 0.0274 (15) | −0.0007 (12) | 0.0000 (12) | 0.0009 (12) |
C3 | 0.0263 (15) | 0.0222 (14) | 0.0331 (16) | 0.0002 (13) | −0.0003 (13) | 0.0059 (12) |
C4 | 0.0207 (14) | 0.0255 (15) | 0.0292 (15) | 0.0030 (13) | 0.0005 (12) | 0.0028 (12) |
C5 | 0.0234 (14) | 0.0237 (15) | 0.0302 (17) | −0.0004 (12) | −0.0017 (12) | −0.0002 (12) |
C6 | 0.0213 (14) | 0.0265 (15) | 0.0300 (16) | 0.0010 (12) | 0.0034 (12) | 0.0016 (13) |
C7 | 0.0236 (14) | 0.0289 (15) | 0.0241 (14) | 0.0094 (13) | 0.0010 (12) | −0.0019 (13) |
C8 | 0.0257 (15) | 0.0249 (15) | 0.0345 (17) | −0.0015 (13) | −0.0001 (13) | −0.0053 (13) |
C9 | 0.0268 (15) | 0.0198 (15) | 0.0327 (16) | 0.0001 (12) | 0.0036 (13) | 0.0018 (12) |
C10 | 0.0221 (14) | 0.0218 (14) | 0.0290 (15) | −0.0021 (12) | −0.0005 (12) | 0.0027 (12) |
C11 | 0.0227 (14) | 0.0224 (14) | 0.0299 (16) | −0.0016 (12) | −0.0024 (12) | 0.0019 (13) |
C12 | 0.0298 (16) | 0.0316 (16) | 0.0289 (16) | 0.0011 (13) | −0.0003 (13) | −0.0002 (13) |
C13 | 0.0304 (16) | 0.0334 (18) | 0.0308 (16) | −0.0055 (15) | −0.0044 (13) | 0.0071 (13) |
C14 | 0.0264 (14) | 0.0265 (16) | 0.0354 (17) | 0.0000 (13) | −0.0050 (13) | 0.0038 (13) |
C15 | 0.0247 (14) | 0.0244 (16) | 0.0329 (16) | −0.0022 (13) | 0.0016 (12) | 0.0015 (13) |
O5 | 0.0473 (14) | 0.0313 (12) | 0.0379 (12) | −0.0007 (11) | 0.0107 (11) | 0.0031 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.211 (3) | C7—C8 | 1.384 (4) |
O2—C1 | 1.332 (4) | C8—C9 | 1.381 (4) |
O2—H2 | 0.8400 | C8—H8 | 0.9500 |
O3—N1 | 1.231 (3) | C9—H9 | 0.9500 |
O4—N1 | 1.238 (3) | C10—C11 | 1.385 (4) |
N1—C7 | 1.450 (4) | C10—C15 | 1.406 (4) |
C1—C2 | 1.505 (4) | C11—C12 | 1.392 (4) |
C2—C3 | 1.347 (4) | C11—H11 | 0.9500 |
C2—C10 | 1.484 (4) | C12—C13 | 1.395 (4) |
C3—C4 | 1.457 (4) | C12—H12 | 0.9500 |
C3—H3 | 0.9500 | C13—C14 | 1.379 (4) |
C4—C9 | 1.398 (4) | C13—H13 | 0.9500 |
C4—C5 | 1.402 (4) | C14—C15 | 1.379 (4) |
C5—C6 | 1.385 (4) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.384 (4) | O5—H51 | 0.8200 |
C6—H6 | 0.9500 | O5—H52 | 0.8200 |
C1—O2—H2 | 109.5 | C9—C8—C7 | 118.2 (3) |
O3—N1—O4 | 122.4 (3) | C9—C8—H8 | 120.9 |
O3—N1—C7 | 118.6 (3) | C7—C8—H8 | 120.9 |
O4—N1—C7 | 119.0 (3) | C8—C9—C4 | 121.6 (3) |
O1—C1—O2 | 123.3 (3) | C8—C9—H9 | 119.2 |
O1—C1—C2 | 123.9 (3) | C4—C9—H9 | 119.2 |
O2—C1—C2 | 112.8 (2) | C11—C10—C15 | 117.7 (3) |
C3—C2—C10 | 121.7 (2) | C11—C10—C2 | 121.5 (2) |
C3—C2—C1 | 121.4 (2) | C15—C10—C2 | 120.8 (3) |
C10—C2—C1 | 116.8 (2) | C10—C11—C12 | 121.7 (3) |
C2—C3—C4 | 129.4 (3) | C10—C11—H11 | 119.1 |
C2—C3—H3 | 115.3 | C12—C11—H11 | 119.1 |
C4—C3—H3 | 115.3 | C11—C12—C13 | 119.6 (3) |
C9—C4—C5 | 118.2 (3) | C11—C12—H12 | 120.2 |
C9—C4—C3 | 118.7 (3) | C13—C12—H12 | 120.2 |
C5—C4—C3 | 123.0 (3) | C14—C13—C12 | 119.1 (3) |
C6—C5—C4 | 121.1 (3) | C14—C13—H13 | 120.4 |
C6—C5—H5 | 119.4 | C12—C13—H13 | 120.4 |
C4—C5—H5 | 119.4 | C13—C14—C15 | 121.1 (3) |
C7—C6—C5 | 118.3 (3) | C13—C14—H14 | 119.5 |
C7—C6—H6 | 120.8 | C15—C14—H14 | 119.5 |
C5—C6—H6 | 120.8 | C14—C15—C10 | 120.8 (3) |
C6—C7—C8 | 122.5 (3) | C14—C15—H15 | 119.6 |
C6—C7—N1 | 118.7 (3) | C10—C15—H15 | 119.6 |
C8—C7—N1 | 118.8 (3) | H51—O5—H52 | 107.2 |
O1—C1—C2—C3 | −64.1 (4) | C6—C7—C8—C9 | −1.6 (4) |
O2—C1—C2—C3 | 117.3 (3) | N1—C7—C8—C9 | 177.7 (3) |
O1—C1—C2—C10 | 112.3 (3) | C7—C8—C9—C4 | −1.4 (4) |
O2—C1—C2—C10 | −66.3 (3) | C5—C4—C9—C8 | 3.6 (4) |
C10—C2—C3—C4 | 175.3 (3) | C3—C4—C9—C8 | −179.0 (3) |
C1—C2—C3—C4 | −8.5 (5) | C3—C2—C10—C11 | 157.0 (3) |
C2—C3—C4—C9 | 151.7 (3) | C1—C2—C10—C11 | −19.4 (4) |
C2—C3—C4—C5 | −31.1 (5) | C3—C2—C10—C15 | −22.6 (4) |
C9—C4—C5—C6 | −3.0 (4) | C1—C2—C10—C15 | 161.0 (3) |
C3—C4—C5—C6 | 179.7 (3) | C15—C10—C11—C12 | 0.9 (4) |
C4—C5—C6—C7 | 0.2 (4) | C2—C10—C11—C12 | −178.7 (3) |
C5—C6—C7—C8 | 2.2 (4) | C10—C11—C12—C13 | 0.3 (5) |
C5—C6—C7—N1 | −177.2 (2) | C11—C12—C13—C14 | −1.0 (4) |
O3—N1—C7—C6 | 10.9 (4) | C12—C13—C14—C15 | 0.6 (4) |
O4—N1—C7—C6 | −170.6 (3) | C13—C14—C15—C10 | 0.6 (4) |
O3—N1—C7—C8 | −168.5 (3) | C11—C10—C15—C14 | −1.3 (4) |
O4—N1—C7—C8 | 10.1 (4) | C2—C10—C15—C14 | 178.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O5 | 0.84 | 1.84 | 2.673 (3) | 171 |
O5—H51···O4i | 0.82 | 2.19 | 2.978 (3) | 161 |
O5—H52···O3ii | 0.82 | 2.39 | 2.935 (3) | 125 |
O5—H52···O1iii | 0.82 | 2.42 | 3.159 (3) | 151 |
C11—H11···O3i | 0.95 | 2.54 | 3.476 (4) | 170 |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z. |