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In the title compound, C16H16N2O4·0.5CH3CH2OH, the Schiff base is approximately planar. An intra­molecular N—H...O hydrogen bond stabilizes the mol­ecular structure. The mol­ecules are linked by O—H...O hydrogen bonds to form a chain along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033290/ci2138sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033290/ci2138Isup2.hkl
Contains datablock I

CCDC reference: 620755

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in solvent or counterion
  • R factor = 0.047
  • wR factor = 0.148
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N'-(4-Hydroxy-3-methoxybenzylidene)-2-methoxybenzohydrazide ethanol hemisolvate top
Crystal data top
C16H16N2O4·0.5C2H6OF(000) = 684
Mr = 323.34Dx = 1.345 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2897 reflections
a = 8.764 (1) Åθ = 2.6–27.0°
b = 8.2705 (9) ŵ = 0.10 mm1
c = 22.348 (3) ÅT = 294 K
β = 99.784 (2)°Block, yellow
V = 1596.3 (3) Å30.22 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2222 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
φ and ω scansh = 108
8355 measured reflectionsk = 99
2823 independent reflectionsl = 2624
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0788P)2 + 0.4458P]
where P = (Fo2 + 2Fc2)/3
2823 reflections(Δ/σ)max = 0.001
234 parametersΔρmax = 0.39 e Å3
21 restraintsΔρmin = 0.28 e Å3
Special details top

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*/UeqOcc. (<1)
O10.1795 (2)0.1938 (2)0.17147 (7)0.0634 (5)
H10.230 (3)0.220 (4)0.1423 (14)0.095*
O20.00731 (17)0.24092 (19)0.24959 (6)0.0596 (4)
O30.75952 (19)0.8105 (2)0.43501 (7)0.0789 (6)
O40.44716 (18)0.7758 (2)0.55440 (6)0.0615 (4)
N10.50813 (19)0.6355 (2)0.39311 (7)0.0490 (4)
N20.5306 (2)0.7116 (2)0.44908 (7)0.0510 (4)
H20.457 (3)0.709 (3)0.4726 (11)0.061*
C10.4277 (2)0.4531 (2)0.28020 (9)0.0474 (5)
H1A0.52580.49950.28600.057*
C20.3780 (2)0.3590 (2)0.22963 (9)0.0485 (5)
H2A0.44350.34190.20160.058*
C30.2319 (2)0.2894 (2)0.21994 (8)0.0460 (5)
C40.1335 (2)0.3145 (2)0.26231 (8)0.0455 (5)
C50.1835 (2)0.4088 (2)0.31258 (8)0.0475 (5)
H50.11780.42650.34050.057*
C60.3307 (2)0.4783 (2)0.32249 (8)0.0456 (5)
C70.3758 (2)0.5705 (2)0.37821 (9)0.0504 (5)
H70.30410.58230.40420.060*
C80.6600 (2)0.7960 (3)0.46738 (9)0.0510 (5)
C90.6813 (2)0.8728 (2)0.52896 (8)0.0487 (5)
C100.8164 (3)0.9622 (3)0.54537 (11)0.0676 (6)
H100.88500.97140.51800.081*
C110.8513 (3)1.0374 (3)0.60100 (13)0.0772 (8)
H110.94161.09780.61080.093*
C120.7521 (3)1.0224 (3)0.64148 (11)0.0750 (8)
H120.77581.07190.67930.090*
C130.6185 (3)0.9356 (3)0.62713 (10)0.0638 (6)
H130.55210.92600.65530.077*
C140.5809 (2)0.8616 (2)0.57084 (8)0.0493 (5)
C150.3345 (3)0.7753 (4)0.59374 (12)0.0766 (7)
H15A0.37750.72480.63150.115*
H15B0.24470.71630.57500.115*
H15C0.30560.88450.60120.115*
C160.1072 (3)0.2580 (3)0.29270 (10)0.0639 (6)
H16A0.05870.21310.33080.096*
H16B0.20250.20200.27860.096*
H16C0.12830.37060.29790.096*
O51.0855 (8)0.6330 (9)0.4678 (3)0.156 (2)0.50
H5A1.00900.69670.45880.234*0.50
C171.0360 (18)0.4833 (13)0.4788 (4)0.118 (4)0.50
H17A1.11970.40700.48250.141*0.50
H17B0.95830.45110.44520.141*0.50
C180.9678 (19)0.4800 (15)0.5388 (6)0.146 (5)0.50
H18A0.93010.37440.54650.219*0.50
H18B1.04640.51180.57210.219*0.50
H18C0.88400.55620.53460.219*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0808 (11)0.0723 (10)0.0407 (8)0.0213 (8)0.0210 (7)0.0160 (7)
O20.0587 (9)0.0760 (10)0.0463 (8)0.0180 (7)0.0154 (6)0.0098 (7)
O30.0695 (10)0.1191 (15)0.0543 (9)0.0295 (10)0.0284 (8)0.0181 (9)
O40.0646 (9)0.0802 (11)0.0440 (8)0.0128 (8)0.0218 (7)0.0070 (7)
N10.0605 (10)0.0528 (10)0.0350 (8)0.0043 (8)0.0124 (7)0.0043 (7)
N20.0576 (10)0.0624 (11)0.0356 (9)0.0104 (8)0.0154 (7)0.0092 (8)
C10.0501 (11)0.0487 (11)0.0453 (10)0.0042 (9)0.0133 (8)0.0012 (9)
C20.0581 (12)0.0494 (11)0.0425 (10)0.0003 (9)0.0215 (9)0.0008 (9)
C30.0619 (12)0.0435 (10)0.0339 (9)0.0020 (9)0.0122 (8)0.0004 (8)
C40.0515 (11)0.0483 (11)0.0375 (10)0.0038 (9)0.0102 (8)0.0018 (8)
C50.0531 (11)0.0526 (11)0.0397 (10)0.0012 (9)0.0163 (8)0.0024 (8)
C60.0550 (11)0.0443 (10)0.0384 (10)0.0012 (9)0.0109 (8)0.0005 (8)
C70.0576 (12)0.0561 (12)0.0408 (10)0.0049 (10)0.0176 (9)0.0056 (9)
C80.0556 (12)0.0601 (12)0.0385 (10)0.0053 (10)0.0115 (9)0.0012 (9)
C90.0547 (11)0.0515 (11)0.0390 (10)0.0027 (9)0.0051 (8)0.0002 (9)
C100.0633 (14)0.0778 (16)0.0599 (14)0.0144 (12)0.0051 (11)0.0031 (12)
C110.0768 (17)0.0731 (17)0.0719 (17)0.0147 (13)0.0149 (14)0.0070 (13)
C120.099 (2)0.0673 (16)0.0509 (14)0.0065 (14)0.0107 (14)0.0147 (11)
C130.0818 (16)0.0660 (14)0.0431 (11)0.0123 (12)0.0092 (11)0.0060 (10)
C140.0602 (12)0.0481 (11)0.0387 (10)0.0044 (9)0.0058 (9)0.0011 (8)
C150.0745 (16)0.102 (2)0.0610 (14)0.0008 (15)0.0341 (12)0.0050 (14)
C160.0550 (13)0.0843 (17)0.0558 (13)0.0122 (11)0.0185 (10)0.0052 (11)
O50.134 (5)0.167 (6)0.170 (5)0.005 (4)0.033 (4)0.016 (5)
C170.144 (7)0.130 (8)0.091 (5)0.009 (6)0.056 (4)0.048 (5)
C180.146 (7)0.092 (5)0.224 (11)0.018 (5)0.101 (8)0.056 (7)
Geometric parameters (Å, º) top
O1—C31.357 (2)C9—C141.393 (3)
O1—H10.88 (3)C10—C111.377 (4)
O2—C41.362 (2)C10—H100.93
O2—C161.415 (2)C11—C121.362 (4)
O3—C81.230 (2)C11—H110.93
O4—C141.366 (3)C12—C131.365 (4)
O4—C151.429 (3)C12—H120.93
N1—C71.271 (3)C13—C141.387 (3)
N1—N21.384 (2)C13—H130.93
N2—C81.335 (3)C15—H15A0.96
N2—H20.90 (3)C15—H15B0.96
C1—C21.381 (3)C15—H15C0.96
C1—C61.390 (3)C16—H16A0.96
C1—H1A0.93C16—H16B0.96
C2—C31.386 (3)C16—H16C0.96
C2—H2A0.93O5—C171.348 (8)
C3—C41.401 (3)O5—H5A0.85
C4—C51.377 (3)C17—C181.560 (8)
C5—C61.395 (3)C17—H17A0.96
C5—H50.93C17—H17B0.96
C6—C71.456 (3)C18—H18A0.96
C7—H70.93C18—H18B0.96
C8—C91.498 (3)C18—H18C0.96
C9—C101.391 (3)
C3—O1—H1108 (2)C12—C11—C10119.3 (2)
C4—O2—C16117.18 (16)C12—C11—H11120.4
C14—O4—C15119.14 (18)C10—C11—H11120.4
C7—N1—N2114.38 (16)C11—C12—C13120.7 (2)
C8—N2—N1119.84 (17)C11—C12—H12119.6
C8—N2—H2119.4 (15)C13—C12—H12119.6
N1—N2—H2120.6 (15)C12—C13—C14120.5 (2)
C2—C1—C6119.78 (18)C12—C13—H13119.8
C2—C1—H1A120.1C14—C13—H13119.8
C6—C1—H1A120.1O4—C14—C13122.26 (19)
C1—C2—C3121.10 (17)O4—C14—C9117.72 (17)
C1—C2—H2A119.5C13—C14—C9120.0 (2)
C3—C2—H2A119.5O4—C15—H15A109.5
O1—C3—C2123.03 (17)O4—C15—H15B109.5
O1—C3—C4117.54 (18)H15A—C15—H15B109.5
C2—C3—C4119.42 (17)O4—C15—H15C109.5
O2—C4—C5125.09 (17)H15A—C15—H15C109.5
O2—C4—C3115.66 (17)H15B—C15—H15C109.5
C5—C4—C3119.25 (18)O2—C16—H16A109.5
C4—C5—C6121.37 (17)O2—C16—H16B109.5
C4—C5—H5119.3H16A—C16—H16B109.5
C6—C5—H5119.3O2—C16—H16C109.5
C1—C6—C5119.08 (17)H16A—C16—H16C109.5
C1—C6—C7123.46 (18)H16B—C16—H16C109.5
C5—C6—C7117.43 (17)C17—O5—H5A110.3
N1—C7—C6123.27 (17)O5—C17—C18110.7 (7)
N1—C7—H7118.4O5—C17—H17A110.7
C6—C7—H7118.4C18—C17—H17A108.2
O3—C8—N2121.39 (19)O5—C17—H17B108.7
O3—C8—C9120.59 (19)C18—C17—H17B110.0
N2—C8—C9118.01 (17)H17A—C17—H17B108.4
C10—C9—C14117.70 (19)C17—C18—H18A111.4
C10—C9—C8115.80 (19)C17—C18—H18B109.4
C14—C9—C8126.50 (18)H18A—C18—H18B109.5
C11—C10—C9121.8 (2)C17—C18—H18C107.6
C11—C10—H10119.1H18A—C18—H18C109.5
C9—C10—H10119.1H18B—C18—H18C109.5
C7—N1—N2—C8174.30 (19)N1—N2—C8—O31.3 (3)
C6—C1—C2—C30.4 (3)N1—N2—C8—C9178.44 (17)
C1—C2—C3—O1178.79 (18)O3—C8—C9—C101.5 (3)
C1—C2—C3—C40.3 (3)N2—C8—C9—C10178.7 (2)
C16—O2—C4—C52.6 (3)O3—C8—C9—C14177.7 (2)
C16—O2—C4—C3177.40 (19)N2—C8—C9—C142.1 (3)
O1—C3—C4—O20.9 (3)C14—C9—C10—C110.1 (4)
C2—C3—C4—O2179.54 (18)C8—C9—C10—C11179.2 (2)
O1—C3—C4—C5179.04 (18)C9—C10—C11—C120.9 (4)
C2—C3—C4—C50.4 (3)C10—C11—C12—C130.8 (4)
O2—C4—C5—C6179.26 (18)C11—C12—C13—C140.3 (4)
C3—C4—C5—C60.7 (3)C15—O4—C14—C136.5 (3)
C2—C1—C6—C50.6 (3)C15—O4—C14—C9173.8 (2)
C2—C1—C6—C7177.52 (18)C12—C13—C14—O4179.0 (2)
C4—C5—C6—C10.8 (3)C12—C13—C14—C91.3 (3)
C4—C5—C6—C7177.45 (18)C10—C9—C14—O4179.08 (19)
N2—N1—C7—C6177.23 (18)C8—C9—C14—O41.7 (3)
C1—C6—C7—N10.2 (3)C10—C9—C14—C131.2 (3)
C5—C6—C7—N1177.93 (19)C8—C9—C14—C13178.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.88 (3)1.90 (3)2.704 (2)152 (3)
N2—H2···O40.90 (3)1.93 (3)2.635 (2)134 (2)
O5—H5A···O30.852.363.185 (7)165
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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