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The title compound, C19H22N2O7·H2O, was synthesized as part of a continuing project involving the structures of hydrazone derivatives. The mol­ecules pack in a three-dimensional framework structure by a combination of O—H...O, O—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015929/fl2117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015929/fl2117Isup2.hkl
Contains datablock I

CCDC reference: 647211

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.151
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.48 Ratio
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-Hydroxy-3,5-dimethoxybenzaldehyde 3,4,5-trimethoxybenzoylhydrazone monohydrate top
Crystal data top
C19H22N2O7·H2OF(000) = 864
Mr = 408.40Dx = 1.384 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2058 reflections
a = 10.1299 (4) Åθ = 2.6–20.6°
b = 13.8108 (6) ŵ = 0.11 mm1
c = 14.8758 (6) ÅT = 273 K
β = 109.598 (2)°Block, colorless
V = 1960.59 (14) Å30.35 × 0.24 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4755 independent reflections
Radiation source: fine-focus sealed tube2463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.963, Tmax = 0.987k = 1818
26378 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.151H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.2386P]
where P = (Fo2 + 2Fc2)/3
4755 reflections(Δ/σ)max < 0.001
270 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Spectroscopic analysis: IR(KBr, ν cm-1): 3548, 3421, 3302, 1645, 1585, 1498, 1448, 1336, 1228, 1119, 995, 956, 847, 735.

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
xyzUiso*/Ueq
O10.41825 (16)0.59052 (10)0.18824 (10)0.0483 (4)
H10.33730.56580.17590.072*
N10.65072 (19)0.89845 (12)0.52125 (11)0.0414 (4)
O40.88358 (16)1.00290 (11)0.59638 (11)0.0547 (4)
N20.67493 (19)0.95359 (12)0.60259 (11)0.0422 (4)
H20.61290.95730.63020.051*
C40.5084 (2)0.77970 (14)0.41801 (14)0.0380 (5)
C100.7970 (2)1.00149 (14)0.63799 (14)0.0384 (5)
O30.23300 (16)0.60942 (11)0.28235 (12)0.0560 (5)
C60.3529 (2)0.66420 (14)0.31426 (15)0.0396 (5)
C90.5420 (2)0.84448 (15)0.49919 (14)0.0414 (5)
H90.48350.84680.53580.050*
C20.5679 (2)0.70600 (15)0.29055 (15)0.0416 (5)
O20.64870 (16)0.69107 (12)0.23428 (11)0.0577 (5)
C10.4439 (2)0.65256 (14)0.26347 (14)0.0377 (5)
C50.3858 (2)0.72654 (15)0.39196 (15)0.0419 (5)
H50.32490.73250.42660.050*
C30.5997 (2)0.76915 (15)0.36591 (15)0.0425 (5)
H30.68200.80500.38250.051*
C120.9597 (3)1.07971 (15)0.77989 (16)0.0500 (6)
H121.02941.06820.75350.060*
C160.7183 (3)1.06946 (15)0.77007 (15)0.0470 (6)
H160.62671.04990.73780.056*
C110.8231 (2)1.05152 (14)0.73139 (14)0.0413 (5)
C150.7513 (3)1.11687 (16)0.85741 (16)0.0519 (6)
O70.6569 (2)1.13903 (14)0.90097 (13)0.0757 (6)
C130.9925 (3)1.12490 (16)0.86734 (17)0.0543 (6)
C140.8884 (3)1.14571 (16)0.90569 (16)0.0539 (7)
O51.1289 (2)1.15187 (14)0.91666 (14)0.0791 (6)
O60.9200 (2)1.19015 (11)0.99286 (11)0.0728 (6)
C80.1112 (3)0.64971 (18)0.2924 (2)0.0622 (7)
H8A0.11310.64110.35680.093*
H8B0.03020.61800.24950.093*
H8C0.10730.71760.27770.093*
C70.7811 (3)0.7373 (2)0.2613 (2)0.0721 (8)
H7A0.76900.80580.26650.108*
H7B0.82430.72510.21400.108*
H7C0.83970.71240.32180.108*
O80.18838 (18)0.47607 (11)0.11171 (11)0.0540 (4)
H170.10620.48560.11320.095 (12)*
H180.18260.46660.05400.114 (13)*
C190.5242 (3)1.0933 (2)0.8685 (2)0.0794 (9)
H19A0.47361.11440.80470.119*
H19B0.47241.11020.90970.119*
H19C0.53651.02440.86900.119*
C180.9269 (4)1.29214 (18)0.9887 (2)0.0865 (10)
H18A1.00171.31040.96620.130*
H190.94381.31861.05120.130*
H18C0.83981.31670.94590.130*
C171.2123 (4)1.0819 (3)0.9733 (3)0.1162 (14)
H17A1.16851.05741.01670.174*
H17B1.30171.10931.00870.174*
H17C1.22501.03000.93400.174*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0465 (10)0.0564 (9)0.0455 (9)0.0080 (7)0.0202 (7)0.0159 (7)
N10.0515 (12)0.0442 (10)0.0297 (9)0.0022 (9)0.0153 (9)0.0053 (8)
O40.0544 (10)0.0669 (10)0.0479 (9)0.0114 (8)0.0238 (8)0.0081 (8)
N20.0492 (12)0.0477 (10)0.0343 (9)0.0066 (9)0.0201 (9)0.0079 (8)
C40.0401 (13)0.0430 (11)0.0315 (11)0.0002 (10)0.0129 (10)0.0012 (9)
C100.0461 (14)0.0381 (11)0.0297 (11)0.0002 (10)0.0112 (10)0.0027 (9)
O30.0461 (10)0.0593 (9)0.0706 (11)0.0166 (8)0.0300 (9)0.0255 (8)
C60.0359 (13)0.0430 (11)0.0408 (12)0.0049 (9)0.0140 (10)0.0020 (9)
C90.0467 (14)0.0467 (12)0.0345 (11)0.0022 (10)0.0187 (10)0.0038 (9)
C20.0383 (13)0.0508 (12)0.0397 (12)0.0001 (10)0.0183 (10)0.0057 (10)
O20.0474 (10)0.0762 (11)0.0620 (11)0.0170 (8)0.0348 (9)0.0278 (9)
C10.0395 (13)0.0408 (11)0.0332 (11)0.0002 (9)0.0129 (10)0.0053 (9)
C50.0433 (14)0.0502 (12)0.0371 (12)0.0020 (10)0.0202 (10)0.0037 (10)
C30.0394 (13)0.0486 (12)0.0409 (12)0.0073 (10)0.0152 (10)0.0065 (10)
C120.0613 (17)0.0430 (12)0.0444 (14)0.0094 (11)0.0163 (12)0.0033 (10)
C160.0568 (15)0.0451 (12)0.0383 (12)0.0006 (11)0.0150 (11)0.0023 (10)
C110.0534 (15)0.0347 (10)0.0334 (11)0.0011 (10)0.0117 (11)0.0004 (9)
C150.0781 (19)0.0431 (12)0.0401 (13)0.0001 (12)0.0273 (13)0.0021 (10)
O70.0960 (15)0.0811 (13)0.0655 (12)0.0144 (11)0.0478 (12)0.0284 (10)
C130.0667 (18)0.0443 (12)0.0435 (13)0.0132 (12)0.0075 (13)0.0010 (11)
C140.086 (2)0.0387 (12)0.0326 (12)0.0116 (12)0.0140 (13)0.0030 (10)
O50.0827 (15)0.0681 (12)0.0651 (12)0.0270 (11)0.0033 (11)0.0064 (10)
O60.1263 (17)0.0483 (10)0.0380 (9)0.0157 (10)0.0199 (10)0.0116 (8)
C80.0443 (15)0.0591 (15)0.0855 (19)0.0085 (12)0.0247 (14)0.0110 (14)
C70.0491 (17)0.096 (2)0.084 (2)0.0170 (15)0.0387 (15)0.0268 (16)
O80.0566 (12)0.0645 (10)0.0431 (10)0.0061 (8)0.0197 (8)0.0097 (8)
C190.091 (2)0.085 (2)0.077 (2)0.0008 (18)0.0470 (18)0.0114 (17)
C180.138 (3)0.0447 (15)0.0678 (19)0.0090 (16)0.0232 (19)0.0164 (13)
C170.080 (3)0.091 (3)0.139 (3)0.006 (2)0.015 (2)0.008 (2)
Geometric parameters (Å, º) top
O1—C11.364 (2)C16—H160.9300
O1—H10.8501C15—O71.357 (3)
N1—C91.278 (3)C15—C141.391 (3)
N1—N21.380 (2)O7—C191.416 (3)
O4—C101.231 (2)C13—O51.380 (3)
N2—C101.345 (3)C13—C141.387 (3)
N2—H20.8600C14—O61.372 (3)
C4—C51.382 (3)O5—C171.371 (4)
C4—C31.399 (3)O6—C181.413 (3)
C4—C91.449 (3)C8—H8A0.9600
C10—C111.494 (3)C8—H8B0.9600
O3—C61.374 (2)C8—H8C0.9600
O3—C81.406 (3)C7—H7A0.9600
C6—C11.383 (3)C7—H7B0.9600
C6—C51.389 (3)C7—H7C0.9600
C9—H90.9300O8—H170.8500
C2—O21.369 (2)O8—H180.8500
C2—C31.371 (3)C19—H19A0.9600
C2—C11.395 (3)C19—H19B0.9600
O2—C71.417 (3)C19—H19C0.9600
C5—H50.9300C18—H18A0.9600
C3—H30.9300C18—H190.9600
C12—C131.379 (3)C18—H18C0.9600
C12—C111.385 (3)C17—H17A0.9600
C12—H120.9300C17—H17B0.9600
C16—C111.389 (3)C17—H17C0.9600
C16—C151.392 (3)
C1—O1—H1109.5C14—C15—C16120.1 (2)
C9—N1—N2115.54 (17)C15—O7—C19118.5 (2)
C10—N2—N1118.97 (17)C12—C13—O5120.3 (2)
C10—N2—H2120.5C12—C13—C14120.4 (2)
N1—N2—H2120.5O5—C13—C14119.3 (2)
C5—C4—C3119.23 (18)O6—C14—C13120.9 (2)
C5—C4—C9119.98 (18)O6—C14—C15119.5 (2)
C3—C4—C9120.79 (19)C13—C14—C15119.6 (2)
O4—C10—N2121.83 (19)C17—O5—C13115.9 (2)
O4—C10—C11121.8 (2)C14—O6—C18113.84 (18)
N2—C10—C11116.38 (18)O3—C8—H8A109.5
C6—O3—C8116.81 (17)O3—C8—H8B109.5
O3—C6—C1114.93 (18)H8A—C8—H8B109.5
O3—C6—C5124.47 (18)O3—C8—H8C109.5
C1—C6—C5120.60 (19)H8A—C8—H8C109.5
N1—C9—C4121.02 (19)H8B—C8—H8C109.5
N1—C9—H9119.5O2—C7—H7A109.5
C4—C9—H9119.5O2—C7—H7B109.5
O2—C2—C3124.86 (19)H7A—C7—H7B109.5
O2—C2—C1114.15 (18)O2—C7—H7C109.5
C3—C2—C1120.97 (18)H7A—C7—H7C109.5
C2—O2—C7117.50 (17)H7B—C7—H7C109.5
O1—C1—C6122.88 (19)H17—O8—H18108.2
O1—C1—C2118.35 (17)O7—C19—H19A109.5
C6—C1—C2118.77 (18)O7—C19—H19B109.5
C4—C5—C6120.29 (18)H19A—C19—H19B109.5
C4—C5—H5119.9O7—C19—H19C109.5
C6—C5—H5119.9H19A—C19—H19C109.5
C2—C3—C4120.11 (19)H19B—C19—H19C109.5
C2—C3—H3119.9O6—C18—H18A109.5
C4—C3—H3119.9O6—C18—H19109.5
C13—C12—C11120.1 (2)H18A—C18—H19109.5
C13—C12—H12120.0O6—C18—H18C109.5
C11—C12—H12120.0H18A—C18—H18C109.5
C11—C16—C15119.6 (2)H19—C18—H18C109.5
C11—C16—H16120.2O5—C17—H17A109.5
C15—C16—H16120.2O5—C17—H17B109.5
C12—C11—C16120.2 (2)H17A—C17—H17B109.5
C12—C11—C10116.7 (2)O5—C17—H17C109.5
C16—C11—C10123.1 (2)H17A—C17—H17C109.5
O7—C15—C14115.5 (2)H17B—C17—H17C109.5
O7—C15—C16124.4 (2)
C9—N1—N2—C10170.63 (18)C13—C12—C11—C160.7 (3)
N1—N2—C10—O45.1 (3)C13—C12—C11—C10178.94 (19)
N1—N2—C10—C11173.93 (16)C15—C16—C11—C120.7 (3)
C8—O3—C6—C1147.5 (2)C15—C16—C11—C10179.76 (19)
C8—O3—C6—C533.3 (3)O4—C10—C11—C1214.8 (3)
N2—N1—C9—C4177.10 (18)N2—C10—C11—C12164.19 (18)
C5—C4—C9—N1176.0 (2)O4—C10—C11—C16165.6 (2)
C3—C4—C9—N14.9 (3)N2—C10—C11—C1615.4 (3)
C3—C2—O2—C76.3 (3)C11—C16—C15—O7179.2 (2)
C1—C2—O2—C7175.5 (2)C11—C16—C15—C140.2 (3)
O3—C6—C1—O10.9 (3)C14—C15—O7—C19165.6 (2)
C5—C6—C1—O1178.31 (19)C16—C15—O7—C1915.0 (4)
O3—C6—C1—C2179.52 (18)C11—C12—C13—O5179.0 (2)
C5—C6—C1—C21.3 (3)C11—C12—C13—C142.4 (3)
O2—C2—C1—O12.0 (3)C12—C13—C14—O6179.6 (2)
C3—C2—C1—O1179.68 (19)O5—C13—C14—O61.8 (3)
O2—C2—C1—C6178.40 (19)C12—C13—C14—C152.8 (3)
C3—C2—C1—C60.1 (3)O5—C13—C14—C15178.6 (2)
C3—C4—C5—C60.7 (3)O7—C15—C14—O62.2 (3)
C9—C4—C5—C6179.93 (19)C16—C15—C14—O6178.34 (19)
O3—C6—C5—C4179.17 (19)O7—C15—C14—C13179.0 (2)
C1—C6—C5—C41.7 (3)C16—C15—C14—C131.5 (3)
O2—C2—C3—C4179.1 (2)C12—C13—O5—C1785.8 (3)
C1—C2—C3—C41.0 (3)C14—C13—O5—C1795.6 (3)
C5—C4—C3—C20.6 (3)C13—C14—O6—C1884.6 (3)
C9—C4—C3—C2178.6 (2)C15—C14—O6—C1898.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O80.851.942.727 (2)154
O1—H1···O30.852.262.704 (2)113
N2—H2···O1i0.862.493.313 (2)160
O8—H17···O4ii0.852.193.033 (2)171
O8—H18···O4iii0.852.172.956 (2)154
O8—H18···N1iii0.852.503.143 (2)133
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x1, y+3/2, z1/2; (iii) x+1, y1/2, z+1/2.
 

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