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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—H...O and C—H...O. Pairs of mol­ecules lie parallel to each other in a head-to-tail fashion, exhibiting strong π–π overlapping.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024329/ww2031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024329/ww2031Isup2.hkl
Contains datablock I

CCDC reference: 618341

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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·H2OF(000) = 600
Mr = 287.26Dx = 1.455 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 26803 reflections
a = 7.578 (2) Åθ = 3.5–28.3°
b = 10.282 (2) ŵ = 0.11 mm1
c = 16.832 (4) ÅT = 173 K
V = 1311.5 (5) Å3Prism, colorless
Z = 40.18 × 0.15 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
1855 independent reflections
Radiation source: fine-focus sealed tube1280 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.116
ω and φ scansθmax = 28.3°, θmin = 3.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 99
Tmin = 0.980, Tmax = 0.987k = 1313
26803 measured reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.08Δρmax = 0.29 e Å3
1855 reflectionsΔρmin = 0.32 e Å3
198 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.026 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: unk
Secondary atom site location: difference Fourier map
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3298 (3)0.5086 (2)0.00396 (12)0.0348 (5)
O20.0644 (3)0.4546 (2)0.04433 (13)0.0338 (5)
H20.09440.38010.02900.051*
O30.1067 (3)0.6981 (2)0.36346 (13)0.0418 (6)
O40.1798 (3)0.9013 (2)0.35863 (13)0.0440 (6)
N10.1389 (3)0.7979 (3)0.32579 (15)0.0322 (6)
C10.1942 (4)0.5385 (3)0.02945 (16)0.0265 (6)
C20.1558 (4)0.6729 (3)0.06034 (16)0.0242 (6)
C30.1413 (4)0.7754 (3)0.01089 (17)0.0272 (6)
H30.13360.85790.03610.033*
C40.1358 (4)0.7783 (3)0.07563 (16)0.0251 (6)
C50.0641 (4)0.6773 (3)0.12139 (16)0.0257 (7)
H50.01580.60320.09560.031*
C60.0623 (4)0.6838 (3)0.20360 (17)0.0259 (7)
H60.01390.61500.23440.031*
C70.1327 (4)0.7929 (3)0.23976 (16)0.0255 (6)
C80.1991 (4)0.8969 (3)0.19692 (18)0.0284 (7)
H80.24400.97170.22310.034*
C90.1981 (4)0.8888 (3)0.11501 (17)0.0264 (7)
H90.24080.96010.08470.032*
C100.1455 (4)0.6883 (3)0.14787 (16)0.0243 (6)
C110.2193 (4)0.5976 (3)0.19887 (18)0.0250 (6)
H110.27550.52300.17720.030*
C120.2131 (4)0.6129 (3)0.28100 (18)0.0301 (7)
H120.26410.54910.31480.036*
C130.1314 (4)0.7223 (3)0.31343 (18)0.0315 (7)
H130.12800.73460.36930.038*
C140.0557 (4)0.8125 (3)0.26324 (18)0.0294 (7)
H140.00100.88680.28500.035*
C150.0611 (4)0.7966 (3)0.18190 (17)0.0273 (7)
H150.00720.85960.14850.033*
O50.1257 (3)0.20779 (19)0.00282 (14)0.0388 (6)
H510.17920.16210.03470.047*
H520.04010.16600.01250.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0319 (12)0.0304 (12)0.0421 (12)0.0031 (10)0.0128 (10)0.0007 (10)
O20.0315 (11)0.0252 (11)0.0446 (13)0.0032 (9)0.0086 (10)0.0063 (10)
O30.0585 (16)0.0366 (14)0.0303 (12)0.0063 (12)0.0058 (11)0.0039 (11)
O40.0616 (16)0.0352 (12)0.0353 (12)0.0094 (13)0.0078 (13)0.0089 (11)
N10.0346 (14)0.0307 (15)0.0314 (14)0.0097 (13)0.0006 (12)0.0038 (12)
C10.0290 (16)0.0279 (15)0.0227 (14)0.0012 (13)0.0011 (13)0.0013 (13)
C20.0198 (13)0.0254 (15)0.0274 (15)0.0007 (12)0.0000 (12)0.0009 (12)
C30.0263 (15)0.0222 (14)0.0331 (16)0.0002 (13)0.0003 (13)0.0059 (12)
C40.0207 (14)0.0255 (15)0.0292 (15)0.0030 (13)0.0005 (12)0.0028 (12)
C50.0234 (14)0.0237 (15)0.0302 (17)0.0004 (12)0.0017 (12)0.0002 (12)
C60.0213 (14)0.0265 (15)0.0300 (16)0.0010 (12)0.0034 (12)0.0016 (13)
C70.0236 (14)0.0289 (15)0.0241 (14)0.0094 (13)0.0010 (12)0.0019 (13)
C80.0257 (15)0.0249 (15)0.0345 (17)0.0015 (13)0.0001 (13)0.0053 (13)
C90.0268 (15)0.0198 (15)0.0327 (16)0.0001 (12)0.0036 (13)0.0018 (12)
C100.0221 (14)0.0218 (14)0.0290 (15)0.0021 (12)0.0005 (12)0.0027 (12)
C110.0227 (14)0.0224 (14)0.0299 (16)0.0016 (12)0.0024 (12)0.0019 (13)
C120.0298 (16)0.0316 (16)0.0289 (16)0.0011 (13)0.0003 (13)0.0002 (13)
C130.0304 (16)0.0334 (18)0.0308 (16)0.0055 (15)0.0044 (13)0.0071 (13)
C140.0264 (14)0.0265 (16)0.0354 (17)0.0000 (13)0.0050 (13)0.0038 (13)
C150.0247 (14)0.0244 (16)0.0329 (16)0.0022 (13)0.0016 (12)0.0015 (13)
O50.0473 (14)0.0313 (12)0.0379 (12)0.0007 (11)0.0107 (11)0.0031 (11)
Geometric parameters (Å, º) top
O1—C11.211 (3)C7—C81.384 (4)
O2—C11.332 (4)C8—C91.381 (4)
O2—H20.8400C8—H80.9500
O3—N11.231 (3)C9—H90.9500
O4—N11.238 (3)C10—C111.385 (4)
N1—C71.450 (4)C10—C151.406 (4)
C1—C21.505 (4)C11—C121.392 (4)
C2—C31.347 (4)C11—H110.9500
C2—C101.484 (4)C12—C131.395 (4)
C3—C41.457 (4)C12—H120.9500
C3—H30.9500C13—C141.379 (4)
C4—C91.398 (4)C13—H130.9500
C4—C51.402 (4)C14—C151.379 (4)
C5—C61.385 (4)C14—H140.9500
C5—H50.9500C15—H150.9500
C6—C71.384 (4)O5—H510.8200
C6—H60.9500O5—H520.8200
C1—O2—H2109.5C9—C8—C7118.2 (3)
O3—N1—O4122.4 (3)C9—C8—H8120.9
O3—N1—C7118.6 (3)C7—C8—H8120.9
O4—N1—C7119.0 (3)C8—C9—C4121.6 (3)
O1—C1—O2123.3 (3)C8—C9—H9119.2
O1—C1—C2123.9 (3)C4—C9—H9119.2
O2—C1—C2112.8 (2)C11—C10—C15117.7 (3)
C3—C2—C10121.7 (2)C11—C10—C2121.5 (2)
C3—C2—C1121.4 (2)C15—C10—C2120.8 (3)
C10—C2—C1116.8 (2)C10—C11—C12121.7 (3)
C2—C3—C4129.4 (3)C10—C11—H11119.1
C2—C3—H3115.3C12—C11—H11119.1
C4—C3—H3115.3C11—C12—C13119.6 (3)
C9—C4—C5118.2 (3)C11—C12—H12120.2
C9—C4—C3118.7 (3)C13—C12—H12120.2
C5—C4—C3123.0 (3)C14—C13—C12119.1 (3)
C6—C5—C4121.1 (3)C14—C13—H13120.4
C6—C5—H5119.4C12—C13—H13120.4
C4—C5—H5119.4C13—C14—C15121.1 (3)
C7—C6—C5118.3 (3)C13—C14—H14119.5
C7—C6—H6120.8C15—C14—H14119.5
C5—C6—H6120.8C14—C15—C10120.8 (3)
C6—C7—C8122.5 (3)C14—C15—H15119.6
C6—C7—N1118.7 (3)C10—C15—H15119.6
C8—C7—N1118.8 (3)H51—O5—H52107.2
O1—C1—C2—C364.1 (4)C6—C7—C8—C91.6 (4)
O2—C1—C2—C3117.3 (3)N1—C7—C8—C9177.7 (3)
O1—C1—C2—C10112.3 (3)C7—C8—C9—C41.4 (4)
O2—C1—C2—C1066.3 (3)C5—C4—C9—C83.6 (4)
C10—C2—C3—C4175.3 (3)C3—C4—C9—C8179.0 (3)
C1—C2—C3—C48.5 (5)C3—C2—C10—C11157.0 (3)
C2—C3—C4—C9151.7 (3)C1—C2—C10—C1119.4 (4)
C2—C3—C4—C531.1 (5)C3—C2—C10—C1522.6 (4)
C9—C4—C5—C63.0 (4)C1—C2—C10—C15161.0 (3)
C3—C4—C5—C6179.7 (3)C15—C10—C11—C120.9 (4)
C4—C5—C6—C70.2 (4)C2—C10—C11—C12178.7 (3)
C5—C6—C7—C82.2 (4)C10—C11—C12—C130.3 (5)
C5—C6—C7—N1177.2 (2)C11—C12—C13—C141.0 (4)
O3—N1—C7—C610.9 (4)C12—C13—C14—C150.6 (4)
O4—N1—C7—C6170.6 (3)C13—C14—C15—C100.6 (4)
O3—N1—C7—C8168.5 (3)C11—C10—C15—C141.3 (4)
O4—N1—C7—C810.1 (4)C2—C10—C15—C14178.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O50.841.842.673 (3)171
O5—H51···O4i0.822.192.978 (3)161
O5—H52···O3ii0.822.392.935 (3)125
O5—H52···O1iii0.822.423.159 (3)151
C11—H11···O3i0.952.543.476 (4)170
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x, y1/2, z+1/2; (iii) x1/2, y+1/2, z.
 

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