Literature DB >> 21579429

2-Hydr-oxy-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)-3-methyl-benzohydrazide monohydrate.

You-Yue Han1, Yong-Hong Li, Qiu-Rong Zhao.   

Abstract

In the title compound, C(16)H(16)N(2)O(4)·H(2)O, the dihedral angle between the two benzene rings is 12.4 (2)° and the mol-ecule adopts an E configuration with respect to the C=N bond. There are intra-molecular O-H⋯N and O-H⋯O hydrogen bonds in the hydrazone mol-ecule, which both generate S(6) rings. In the crystal structure, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming layers parallel to the ab plane. The crystal studied was a non-merohedral twin with a domain ratio of 0.887 (3):0.113 (3).

Entities:  

Year:  2010        PMID： 21579429      PMCID： PMC2979542          DOI： 10.1107/S1600536810016855

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For our previous studies on hydrazones and for background information, see: Han & Zhao (2010a ▶,b ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O4·H2O M = 318.32 Monoclinic, a = 4.488 (1) Å b = 13.494 (2) Å c = 26.089 (3) Å β = 91.630 (2)° V = 1579.3 (5) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.980, T max = 0.982 3429 measured reflections 3429 independent reflections 1584 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.136 S = 0.82 3429 reflections 211 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016855/hb5423sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016855/hb5423Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H16N2O4·H2OF(000) = 672
Mr = 318.32Dx = 1.339 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1505 reflections
a = 4.488 (1) Åθ = 2.7–24.3°
b = 13.494 (2) ŵ = 0.10 mm−1
c = 26.089 (3) ÅT = 298 K
β = 91.630 (2)°Block, colorless
V = 1579.3 (5) Å30.20 × 0.20 × 0.18 mm
Z = 4
Bruker SMART CCD diffractometer3429 independent reflections
Radiation source: fine-focus sealed tube1584 reflections with I > 2σ(I)
graphiteRint = 0.0000
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −5→5
Tmin = 0.980, Tmax = 0.982k = −17→17
3429 measured reflectionsl = 0→33
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 0.82w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
3429 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
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.
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.
xyzUiso*/Ueq
O1−0.0603 (4)0.34424 (11)0.17742 (7)0.0707 (5)
H10.04160.36190.20240.106*
O2−0.7266 (4)0.47988 (12)0.05036 (6)0.0682 (5)
O30.4757 (4)0.34626 (11)0.30448 (6)0.0750 (6)
O40.8037 (4)0.30326 (11)0.38168 (7)0.0774 (6)
H40.68570.29400.35750.116*
N10.2277 (4)0.47228 (14)0.23782 (7)0.0548 (5)
N20.4287 (4)0.50268 (14)0.27598 (7)0.0529 (5)
H20.46170.56810.27790.063*
C1−0.1155 (5)0.52186 (16)0.17115 (8)0.0501 (6)
C2−0.1891 (5)0.42542 (16)0.15477 (8)0.0507 (6)
C3−0.3910 (5)0.40878 (16)0.11519 (8)0.0528 (6)
H3−0.43810.34430.10530.063*
C4−0.5233 (5)0.48799 (16)0.09027 (8)0.0516 (6)
C5−0.4595 (6)0.58423 (17)0.10571 (9)0.0579 (6)
H5−0.55390.63750.08950.069*
C6−0.2570 (5)0.60000 (17)0.14486 (9)0.0571 (7)
H6−0.21160.66480.15440.069*
C7−0.7804 (7)0.38437 (19)0.02939 (10)0.0779 (9)
H7A−0.59700.35710.01770.117*
H7B−0.92110.38940.00110.117*
H7C−0.85970.34200.05520.117*
C80.0983 (5)0.54235 (18)0.21216 (9)0.0533 (6)
H80.14370.60780.22030.064*
C90.5468 (6)0.43567 (17)0.30853 (9)0.0527 (6)
C100.7606 (5)0.46971 (15)0.34903 (8)0.0482 (6)
C110.8747 (6)0.40063 (16)0.38452 (9)0.0560 (6)
C121.0734 (6)0.42876 (19)0.42418 (9)0.0626 (7)
C131.1545 (6)0.52613 (19)0.42727 (10)0.0713 (8)
H131.28650.54620.45340.086*
C141.0462 (6)0.59542 (18)0.39284 (10)0.0693 (8)
H141.10570.66120.39590.083*
C150.8526 (6)0.56823 (17)0.35429 (9)0.0586 (7)
H150.78080.61570.33120.070*
C161.1935 (7)0.3513 (2)0.46131 (10)0.0915 (10)
H16A1.32860.38200.48570.137*
H16B1.29690.30110.44280.137*
H16C1.03130.32180.47900.137*
O50.4807 (5)0.71679 (11)0.27610 (6)0.0787 (6)
H5A0.34140.73830.29400.118*
H5B0.52240.75690.25280.118*
U11U22U33U12U13U23
O10.0818 (13)0.0494 (10)0.0792 (12)−0.0028 (9)−0.0243 (10)0.0088 (8)
O20.0772 (13)0.0656 (11)0.0607 (10)0.0033 (10)−0.0179 (10)−0.0049 (8)
O30.1079 (16)0.0447 (10)0.0717 (12)−0.0132 (10)−0.0130 (10)−0.0080 (8)
O40.1079 (16)0.0432 (10)0.0804 (13)0.0016 (10)−0.0083 (11)0.0055 (8)
N10.0563 (13)0.0572 (12)0.0505 (11)−0.0060 (10)−0.0044 (10)−0.0047 (10)
N20.0592 (13)0.0466 (10)0.0524 (12)−0.0060 (10)−0.0057 (10)−0.0047 (9)
C10.0540 (15)0.0509 (14)0.0454 (13)−0.0051 (12)0.0009 (12)−0.0036 (11)
C20.0554 (16)0.0456 (13)0.0512 (13)−0.0011 (12)0.0017 (12)0.0048 (11)
C30.0545 (15)0.0468 (13)0.0568 (15)−0.0027 (12)−0.0045 (12)−0.0056 (11)
C40.0558 (15)0.0541 (14)0.0447 (13)0.0000 (12)−0.0014 (12)−0.0044 (11)
C50.0660 (17)0.0483 (13)0.0591 (15)0.0080 (13)−0.0030 (13)0.0046 (11)
C60.0646 (17)0.0449 (13)0.0616 (16)−0.0051 (12)0.0000 (14)−0.0026 (11)
C70.086 (2)0.0762 (19)0.0699 (18)−0.0058 (17)−0.0192 (15)−0.0202 (15)
C80.0521 (15)0.0521 (14)0.0556 (14)−0.0075 (12)0.0005 (12)−0.0052 (12)
C90.0694 (17)0.0417 (13)0.0470 (13)−0.0014 (12)0.0046 (12)−0.0046 (11)
C100.0573 (15)0.0429 (12)0.0445 (13)0.0017 (11)0.0012 (11)−0.0044 (10)
C110.0699 (18)0.0465 (14)0.0518 (14)0.0044 (13)0.0070 (13)−0.0021 (11)
C120.0727 (19)0.0635 (16)0.0515 (15)0.0114 (15)−0.0028 (13)0.0005 (13)
C130.078 (2)0.0724 (18)0.0620 (17)0.0062 (16)−0.0158 (15)−0.0129 (14)
C140.086 (2)0.0499 (14)0.0707 (18)−0.0079 (14)−0.0158 (16)−0.0095 (13)
C150.0698 (18)0.0456 (13)0.0601 (15)0.0024 (13)−0.0052 (13)−0.0020 (11)
C160.112 (3)0.092 (2)0.0700 (19)0.034 (2)−0.0149 (17)0.0079 (16)
O50.1172 (17)0.0435 (9)0.0748 (12)0.0068 (10)−0.0079 (11)0.0063 (8)
O1—C21.365 (3)C7—H7A0.9600
O1—H10.8208C7—H7B0.9600
O2—C41.369 (3)C7—H7C0.9600
O2—C71.418 (3)C8—H80.9300
O3—C91.252 (3)C9—C101.480 (3)
O4—C111.354 (3)C10—C151.398 (3)
O4—H40.8210C10—C111.400 (3)
N1—C81.287 (3)C11—C121.399 (3)
N1—N21.387 (2)C12—C131.365 (3)
N2—C91.339 (3)C12—C161.514 (3)
N2—H20.8961C13—C141.375 (3)
C1—C61.400 (3)C13—H130.9300
C1—C21.406 (3)C14—C151.361 (3)
C1—C81.443 (3)C14—H140.9300
C2—C31.373 (3)C15—H150.9300
C3—C41.377 (3)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.387 (3)C16—H16C0.9600
C5—C61.364 (3)O5—H5A0.8417
C5—H50.9300O5—H5B0.8395
C6—H60.9300
C2—O1—H1109.3N1—C8—C1121.7 (2)
C4—O2—C7117.94 (18)N1—C8—H8119.2
C11—O4—H4109.6C1—C8—H8119.2
C8—N1—N2115.52 (18)O3—C9—N2120.1 (2)
C9—N2—N1119.55 (19)O3—C9—C10121.2 (2)
C9—N2—H2124.6N2—C9—C10118.68 (19)
N1—N2—H2115.8C15—C10—C11117.8 (2)
C6—C1—C2116.7 (2)C15—C10—C9123.3 (2)
C6—C1—C8120.1 (2)C11—C10—C9118.9 (2)
C2—C1—C8123.2 (2)O4—C11—C12116.6 (2)
O1—C2—C3117.17 (19)O4—C11—C10121.9 (2)
O1—C2—C1121.21 (19)C12—C11—C10121.4 (2)
C3—C2—C1121.6 (2)C13—C12—C11117.9 (2)
C2—C3—C4119.7 (2)C13—C12—C16122.5 (2)
C2—C3—H3120.2C11—C12—C16119.6 (2)
C4—C3—H3120.2C12—C13—C14121.8 (2)
O2—C4—C3124.5 (2)C12—C13—H13119.1
O2—C4—C5115.0 (2)C14—C13—H13119.1
C3—C4—C5120.5 (2)C15—C14—C13120.4 (2)
C6—C5—C4119.4 (2)C15—C14—H14119.8
C6—C5—H5120.3C13—C14—H14119.8
C4—C5—H5120.3C14—C15—C10120.7 (2)
C5—C6—C1122.2 (2)C14—C15—H15119.7
C5—C6—H6118.9C10—C15—H15119.7
C1—C6—H6118.9C12—C16—H16A109.5
O2—C7—H7A109.5C12—C16—H16B109.5
O2—C7—H7B109.5H16A—C16—H16B109.5
H7A—C7—H7B109.5C12—C16—H16C109.5
O2—C7—H7C109.5H16A—C16—H16C109.5
H7A—C7—H7C109.5H16B—C16—H16C109.5
H7B—C7—H7C109.5H5A—O5—H5B111.4
C8—N1—N2—C9172.1 (2)N1—N2—C9—C10−179.92 (19)
C6—C1—C2—O1179.1 (2)O3—C9—C10—C15178.3 (2)
C8—C1—C2—O10.3 (4)N2—C9—C10—C15−1.8 (4)
C6—C1—C2—C3−0.4 (4)O3—C9—C10—C11−2.6 (4)
C8—C1—C2—C3−179.2 (2)N2—C9—C10—C11177.2 (2)
O1—C2—C3—C4−178.7 (2)C15—C10—C11—O4−178.4 (2)
C1—C2—C3—C40.8 (4)C9—C10—C11—O42.5 (4)
C7—O2—C4—C3−7.4 (4)C15—C10—C11—C120.3 (4)
C7—O2—C4—C5174.0 (2)C9—C10—C11—C12−178.9 (2)
C2—C3—C4—O2179.9 (2)O4—C11—C12—C13178.5 (3)
C2—C3—C4—C5−1.6 (4)C10—C11—C12—C13−0.2 (4)
O2—C4—C5—C6−179.3 (2)O4—C11—C12—C16−0.6 (4)
C3—C4—C5—C62.0 (4)C10—C11—C12—C16−179.3 (3)
C4—C5—C6—C1−1.7 (4)C11—C12—C13—C140.1 (4)
C2—C1—C6—C50.8 (4)C16—C12—C13—C14179.2 (3)
C8—C1—C6—C5179.7 (2)C12—C13—C14—C150.0 (5)
N2—N1—C8—C1179.8 (2)C13—C14—C15—C100.0 (4)
C6—C1—C8—N1178.5 (2)C11—C10—C15—C14−0.2 (4)
C2—C1—C8—N1−2.7 (4)C9—C10—C15—C14178.9 (2)
N1—N2—C9—O3−0.1 (4)
D—H···AD—HH···AD···AD—H···A
O4—H4···O30.821.802.528 (2)148
O1—H1···N10.821.932.650 (2)146
N2—H2···O50.902.012.899 (2)172
O5—H5B···O3i0.841.922.745 (2)167
O5—H5A···O1ii0.842.062.849 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H4⋯O30.821.802.528 (2)148
O1—H1⋯N10.821.932.650 (2)146
N2—H2⋯O50.902.012.899 (2)172
O5—H5B⋯O3i0.841.922.745 (2)167
O5—H5A⋯O1ii0.842.062.849 (3)156

Symmetry codes: (i) ; (ii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  N'-(2-Chloro-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

Authors:  You-Yue Han; Qiu-Rong Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-02

3.  N'-(2,3-Dimethoxy-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

Authors:  You-Yue Han; Qiu-Rong Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-02
  3 in total

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