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The asymmetric unit of the title compound, C18H20N2O5·H2O, consists of a benzohydrazide mol­ecule which exists in an E conformation with respect to the C=N imine bond and a water mol­ecule. The dihedral angle between the aromatic rings is 41.67 (9)°. The meth­oxy substituent of the 4-meth­oxy­phenyl group is twisted at an angle of 6.8 (3)° out of the plane of the attached benzene ring. In the 2,4,5-tri­meth­oxy­phenyl unit, the para-meth­oxy group is coplanar with the ring [C—C—O—C = −1.5 (3)°], whereas the ortho- and meta-meth­oxy groups are twisted out of the plane of the ring [C—C—O—C = 75.4 (2) and −67.1 (2)°, respectively]. Two mol­ecules are connected by two water mol­ecules via O—H...O hydrogen bonds, generating an R22(8) ring motif. One of the water H atoms forms an additional hydrogen bond to an N atom. The water mol­ecules act as an acceptor for an N—H...O hydrogen bond. As a result, a three-dimensional network is formed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616015261/bt4029sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616015261/bt4029Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616015261/bt4029Isup3.cml
Supplementary material

CCDC reference: 1507058

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.145
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -2.956 Report PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 3 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 3 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 39 Note PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-4-Methoxy-N'-(2,3,4-trimethoxybenzylidene)benzohydrazide monohydrate top
Crystal data top
C18H20N2O5·H2OF(000) = 768
Mr = 362.37Dx = 1.282 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.1090 (9) ÅCell parameters from 2417 reflections
b = 11.2205 (5) Åθ = 2.1–28.3°
c = 10.7515 (5) ŵ = 0.10 mm1
β = 104.888 (2)°T = 295 K
V = 1878.11 (16) Å3Block, colourless
Z = 40.30 × 0.28 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2334 reflections with I > 2σ(I)
ω and φ scanRint = 0.037
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
θmax = 28.4°, θmin = 2.6°
Tmin = 0.962, Tmax = 0.986h = 2119
14944 measured reflectionsk = 1514
4685 independent reflectionsl = 1114
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0658P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
4685 reflectionsΔρmax = 0.18 e Å3
249 parametersΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.24421 (17)0.0490 (2)0.1222 (3)0.0886 (8)
H1A1.2803610.0690280.1774900.133*
H1B1.1936120.0091060.1712450.133*
H1C1.2748690.0027020.0547300.133*
C21.16371 (12)0.14659 (18)0.00676 (19)0.0545 (5)
C31.13670 (13)0.25364 (18)0.0479 (2)0.0647 (6)
H31.1580280.3251700.0251870.078*
C41.07928 (13)0.25478 (17)0.1212 (2)0.0581 (5)
H41.0610020.3272460.1467450.070*
C51.04751 (11)0.14890 (16)0.15839 (16)0.0447 (4)
C61.07691 (12)0.04319 (16)0.11999 (17)0.0471 (5)
H61.0576050.0283260.1461810.056*
C71.13406 (12)0.04018 (17)0.04393 (18)0.0504 (5)
H71.1523230.0321920.0181200.060*
C80.98183 (12)0.14453 (16)0.23180 (17)0.0474 (5)
C90.79901 (11)0.31185 (16)0.22430 (16)0.0442 (4)
H90.8036030.3615900.1571940.053*
C100.72665 (11)0.32514 (15)0.27982 (15)0.0403 (4)
C110.66504 (12)0.41359 (15)0.23211 (16)0.0437 (4)
C120.59547 (12)0.42884 (16)0.28314 (17)0.0497 (5)
C130.58618 (12)0.35767 (16)0.38446 (17)0.0506 (5)
C140.64630 (12)0.26918 (16)0.43072 (17)0.0512 (5)
H140.6402080.2201520.4975560.061*
C150.71445 (12)0.25373 (16)0.37852 (16)0.0469 (5)
H150.7537880.1934220.4102680.056*
C160.69663 (16)0.6007 (2)0.1529 (2)0.0836 (8)
H16A0.6578510.6392640.1945220.125*
H16B0.6948920.6405620.0732010.125*
H16C0.7539160.6040940.2077600.125*
C170.45299 (16)0.4792 (2)0.1714 (3)0.1005 (10)
H17A0.4479060.4730420.0807140.151*
H17B0.4119000.5358570.1862050.151*
H17C0.4422360.4027740.2042900.151*
C180.50355 (17)0.3094 (2)0.5323 (2)0.0897 (8)
H18A0.4948950.2281350.5038430.135*
H18B0.4536810.3372320.5567950.135*
H18C0.5527530.3141000.6048110.135*
N20.85666 (10)0.23302 (13)0.26582 (14)0.0473 (4)
N10.92169 (10)0.23108 (14)0.20414 (15)0.0483 (4)
O11.22019 (10)0.15475 (13)0.06744 (16)0.0771 (5)
O20.97921 (8)0.06501 (12)0.31030 (13)0.0609 (4)
O30.67178 (9)0.47970 (11)0.12780 (12)0.0582 (4)
O40.53704 (9)0.51746 (12)0.23501 (15)0.0699 (4)
O50.51735 (10)0.38125 (13)0.43079 (14)0.0729 (4)
O60.89533 (9)0.42585 (12)0.02007 (13)0.0578 (4)
H10.9222 (11)0.2829 (13)0.1455 (13)0.051 (5)*
H6A0.9271 (12)0.4808 (15)0.0652 (18)0.076*
H6B0.9070 (14)0.417 (2)0.0528 (13)0.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0936 (19)0.0836 (18)0.1047 (19)0.0148 (14)0.0550 (16)0.0022 (15)
C20.0486 (11)0.0563 (13)0.0610 (12)0.0044 (9)0.0182 (10)0.0093 (10)
C30.0633 (14)0.0437 (11)0.0948 (16)0.0003 (10)0.0341 (12)0.0114 (11)
C40.0572 (12)0.0415 (11)0.0798 (14)0.0042 (9)0.0252 (11)0.0023 (10)
C50.0427 (10)0.0435 (10)0.0459 (10)0.0040 (8)0.0076 (8)0.0055 (8)
C60.0474 (11)0.0412 (10)0.0490 (10)0.0014 (8)0.0058 (9)0.0077 (8)
C70.0517 (12)0.0439 (11)0.0533 (11)0.0069 (9)0.0092 (9)0.0020 (9)
C80.0500 (11)0.0440 (10)0.0453 (10)0.0018 (9)0.0069 (9)0.0025 (9)
C90.0482 (11)0.0444 (10)0.0370 (9)0.0022 (8)0.0056 (8)0.0016 (8)
C100.0429 (10)0.0391 (9)0.0359 (9)0.0022 (8)0.0047 (7)0.0006 (8)
C110.0525 (11)0.0402 (10)0.0356 (9)0.0003 (8)0.0066 (8)0.0016 (8)
C120.0597 (13)0.0402 (10)0.0477 (10)0.0121 (9)0.0112 (9)0.0041 (9)
C130.0547 (12)0.0516 (11)0.0477 (11)0.0070 (9)0.0169 (9)0.0020 (9)
C140.0599 (12)0.0486 (11)0.0447 (10)0.0027 (9)0.0129 (9)0.0086 (9)
C150.0489 (11)0.0436 (10)0.0452 (10)0.0045 (8)0.0069 (8)0.0059 (9)
C160.0892 (18)0.0592 (14)0.0907 (17)0.0149 (12)0.0019 (14)0.0268 (13)
C170.0813 (19)0.099 (2)0.103 (2)0.0370 (15)0.0102 (16)0.0022 (16)
C180.1019 (19)0.0920 (18)0.0959 (18)0.0139 (16)0.0632 (16)0.0193 (15)
N20.0458 (9)0.0488 (9)0.0476 (8)0.0028 (7)0.0125 (7)0.0042 (7)
N10.0503 (10)0.0473 (9)0.0489 (9)0.0064 (7)0.0155 (7)0.0119 (8)
O10.0806 (11)0.0649 (10)0.1004 (12)0.0059 (8)0.0497 (9)0.0103 (9)
O20.0664 (9)0.0581 (8)0.0600 (8)0.0134 (7)0.0195 (7)0.0202 (7)
O30.0713 (9)0.0526 (8)0.0499 (8)0.0039 (7)0.0141 (6)0.0169 (6)
O40.0737 (11)0.0588 (9)0.0795 (10)0.0268 (8)0.0236 (8)0.0181 (7)
O50.0831 (11)0.0767 (10)0.0708 (9)0.0247 (8)0.0414 (8)0.0134 (8)
O60.0684 (10)0.0563 (9)0.0507 (8)0.0118 (7)0.0189 (7)0.0035 (7)
Geometric parameters (Å, º) top
C1—O11.422 (3)C11—C121.379 (3)
C1—H1A0.9600C12—O41.376 (2)
C1—H1B0.9600C12—C131.389 (3)
C1—H1C0.9600C13—O51.353 (2)
C2—O11.359 (2)C13—C141.387 (2)
C2—C71.383 (3)C14—C151.366 (2)
C2—C31.388 (3)C14—H140.9300
C3—C41.361 (3)C15—H150.9300
C3—H30.9300C16—O31.422 (2)
C4—C51.392 (3)C16—H16A0.9600
C4—H40.9300C16—H16B0.9600
C5—C61.379 (2)C16—H16C0.9600
C5—C81.474 (3)C17—O41.418 (3)
C6—C71.380 (3)C17—H17A0.9600
C6—H60.9300C17—H17B0.9600
C7—H70.9300C17—H17C0.9600
C8—O21.236 (2)C18—O51.420 (3)
C8—N11.350 (2)C18—H18A0.9600
C9—N21.277 (2)C18—H18B0.9600
C9—C101.447 (2)C18—H18C0.9600
C9—H90.9300N2—N11.376 (2)
C10—C151.383 (2)N1—H10.859 (9)
C10—C111.404 (2)O6—H6A0.865 (9)
C11—O31.372 (2)O6—H6B0.858 (9)
O1—C1—H1A109.5C11—C12—C13120.19 (16)
O1—C1—H1B109.5O5—C13—C14124.80 (18)
H1A—C1—H1B109.5O5—C13—C12116.09 (16)
O1—C1—H1C109.5C14—C13—C12119.11 (19)
H1A—C1—H1C109.5C15—C14—C13120.29 (17)
H1B—C1—H1C109.5C15—C14—H14119.9
O1—C2—C7124.14 (18)C13—C14—H14119.9
O1—C2—C3116.16 (18)C14—C15—C10121.95 (16)
C7—C2—C3119.7 (2)C14—C15—H15119.0
C4—C3—C2120.54 (19)C10—C15—H15119.0
C4—C3—H3119.7O3—C16—H16A109.5
C2—C3—H3119.7O3—C16—H16B109.5
C3—C4—C5120.87 (18)H16A—C16—H16B109.5
C3—C4—H4119.6O3—C16—H16C109.5
C5—C4—H4119.6H16A—C16—H16C109.5
C6—C5—C4117.90 (18)H16B—C16—H16C109.5
C6—C5—C8118.71 (16)O4—C17—H17A109.5
C4—C5—C8123.33 (17)O4—C17—H17B109.5
C5—C6—C7122.08 (17)H17A—C17—H17B109.5
C5—C6—H6119.0O4—C17—H17C109.5
C7—C6—H6119.0H17A—C17—H17C109.5
C6—C7—C2118.87 (18)H17B—C17—H17C109.5
C6—C7—H7120.6O5—C18—H18A109.5
C2—C7—H7120.6O5—C18—H18B109.5
O2—C8—N1121.41 (19)H18A—C18—H18B109.5
O2—C8—C5122.99 (17)O5—C18—H18C109.5
N1—C8—C5115.55 (16)H18A—C18—H18C109.5
N2—C9—C10121.17 (16)H18B—C18—H18C109.5
N2—C9—H9119.4C9—N2—N1114.68 (15)
C10—C9—H9119.4C8—N1—N2119.82 (16)
C15—C10—C11117.60 (17)C8—N1—H1120.5 (12)
C15—C10—C9123.02 (16)N2—N1—H1119.6 (12)
C11—C10—C9119.39 (16)C2—O1—C1118.76 (17)
O3—C11—C12120.08 (16)C11—O3—C16116.04 (15)
O3—C11—C10118.94 (17)C12—O4—C17116.03 (16)
C12—C11—C10120.84 (16)C13—O5—C18118.47 (17)
O4—C12—C11119.17 (17)H6A—O6—H6B111 (2)
O4—C12—C13120.61 (18)
O1—C2—C3—C4179.10 (18)C10—C11—C12—C131.1 (3)
C7—C2—C3—C42.0 (3)O4—C12—C13—O50.1 (3)
C2—C3—C4—C51.1 (3)C11—C12—C13—O5178.15 (16)
C3—C4—C5—C60.8 (3)O4—C12—C13—C14179.95 (16)
C3—C4—C5—C8176.64 (17)C11—C12—C13—C141.9 (3)
C4—C5—C6—C71.9 (3)O5—C13—C14—C15178.97 (17)
C8—C5—C6—C7175.68 (16)C12—C13—C14—C151.1 (3)
C5—C6—C7—C21.0 (3)C13—C14—C15—C100.6 (3)
O1—C2—C7—C6179.75 (17)C11—C10—C15—C141.4 (2)
C3—C2—C7—C61.0 (3)C9—C10—C15—C14178.98 (16)
C6—C5—C8—O234.9 (2)C10—C9—N2—N1179.79 (14)
C4—C5—C8—O2147.69 (19)O2—C8—N1—N21.2 (3)
C6—C5—C8—N1142.51 (16)C5—C8—N1—N2178.68 (14)
C4—C5—C8—N134.9 (2)C9—N2—N1—C8173.92 (15)
N2—C9—C10—C150.9 (2)C7—C2—O1—C16.8 (3)
N2—C9—C10—C11179.46 (16)C3—C2—O1—C1174.4 (2)
C15—C10—C11—O3175.04 (14)C12—C11—O3—C1675.4 (2)
C9—C10—C11—O34.6 (2)C10—C11—O3—C16108.9 (2)
C15—C10—C11—C120.6 (2)C11—C12—O4—C17114.9 (2)
C9—C10—C11—C12179.80 (15)C13—C12—O4—C1767.1 (2)
O3—C11—C12—O45.3 (3)C14—C13—O5—C181.5 (3)
C10—C11—C12—O4179.15 (15)C12—C13—O5—C18178.49 (19)
O3—C11—C12—C13176.63 (16)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O60.86 (1)2.07 (1)2.905 (2)164 (2)
C9—H9···O60.932.453.258 (2)146
O6—H6A···O2i0.87 (1)1.98 (1)2.8204 (18)163 (2)
O6—H6B···O2ii0.86 (1)2.11 (1)2.914 (2)156 (2)
O6—H6B···N2ii0.86 (1)2.54 (2)3.1880 (19)133 (2)
C1—H1C···Cg2iii0.962.953.900 (3)171
C16—H16C···Cg1i0.962.793.713 (2)162
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2.
 

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