The asymmetric unit of the title compound, C
18H
20N
2O
5·H
2O, 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
CCDC reference: 1507058
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(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
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·H2O | F(000) = 768 |
Mr = 362.37 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.1090 (9) Å | Cell parameters from 2417 reflections |
b = 11.2205 (5) Å | θ = 2.1–28.3° |
c = 10.7515 (5) Å | µ = 0.10 mm−1 |
β = 104.888 (2)° | T = 295 K |
V = 1878.11 (16) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.28 × 0.24 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 2334 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 28.4°, θmin = 2.6° |
Tmin = 0.962, Tmax = 0.986 | h = −21→19 |
14944 measured reflections | k = −15→14 |
4685 independent reflections | l = −11→14 |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H 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 reflections | Δρmax = 0.18 e Å−3 |
249 parameters | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 1.24421 (17) | 0.0490 (2) | −0.1222 (3) | 0.0886 (8) | |
H1A | 1.280361 | 0.069028 | −0.177490 | 0.133* | |
H1B | 1.193612 | 0.009106 | −0.171245 | 0.133* | |
H1C | 1.274869 | −0.002702 | −0.054730 | 0.133* | |
C2 | 1.16371 (12) | 0.14659 (18) | 0.00676 (19) | 0.0545 (5) | |
C3 | 1.13670 (13) | 0.25364 (18) | 0.0479 (2) | 0.0647 (6) | |
H3 | 1.158028 | 0.325170 | 0.025187 | 0.078* | |
C4 | 1.07928 (13) | 0.25478 (17) | 0.1212 (2) | 0.0581 (5) | |
H4 | 1.061002 | 0.327246 | 0.146745 | 0.070* | |
C5 | 1.04751 (11) | 0.14890 (16) | 0.15839 (16) | 0.0447 (4) | |
C6 | 1.07691 (12) | 0.04319 (16) | 0.11999 (17) | 0.0471 (5) | |
H6 | 1.057605 | −0.028326 | 0.146181 | 0.056* | |
C7 | 1.13406 (12) | 0.04018 (17) | 0.04393 (18) | 0.0504 (5) | |
H7 | 1.152323 | −0.032192 | 0.018120 | 0.060* | |
C8 | 0.98183 (12) | 0.14453 (16) | 0.23180 (17) | 0.0474 (5) | |
C9 | 0.79901 (11) | 0.31185 (16) | 0.22430 (16) | 0.0442 (4) | |
H9 | 0.803603 | 0.361590 | 0.157194 | 0.053* | |
C10 | 0.72665 (11) | 0.32514 (15) | 0.27982 (15) | 0.0403 (4) | |
C11 | 0.66504 (12) | 0.41359 (15) | 0.23211 (16) | 0.0437 (4) | |
C12 | 0.59547 (12) | 0.42884 (16) | 0.28314 (17) | 0.0497 (5) | |
C13 | 0.58618 (12) | 0.35767 (16) | 0.38446 (17) | 0.0506 (5) | |
C14 | 0.64630 (12) | 0.26918 (16) | 0.43072 (17) | 0.0512 (5) | |
H14 | 0.640208 | 0.220152 | 0.497556 | 0.061* | |
C15 | 0.71445 (12) | 0.25373 (16) | 0.37852 (16) | 0.0469 (5) | |
H15 | 0.753788 | 0.193422 | 0.410268 | 0.056* | |
C16 | 0.69663 (16) | 0.6007 (2) | 0.1529 (2) | 0.0836 (8) | |
H16A | 0.657851 | 0.639264 | 0.194522 | 0.125* | |
H16B | 0.694892 | 0.640562 | 0.073201 | 0.125* | |
H16C | 0.753916 | 0.604094 | 0.207760 | 0.125* | |
C17 | 0.45299 (16) | 0.4792 (2) | 0.1714 (3) | 0.1005 (10) | |
H17A | 0.447906 | 0.473042 | 0.080714 | 0.151* | |
H17B | 0.411900 | 0.535857 | 0.186205 | 0.151* | |
H17C | 0.442236 | 0.402774 | 0.204290 | 0.151* | |
C18 | 0.50355 (17) | 0.3094 (2) | 0.5323 (2) | 0.0897 (8) | |
H18A | 0.494895 | 0.228135 | 0.503843 | 0.135* | |
H18B | 0.453681 | 0.337232 | 0.556795 | 0.135* | |
H18C | 0.552753 | 0.314100 | 0.604811 | 0.135* | |
N2 | 0.85666 (10) | 0.23302 (13) | 0.26582 (14) | 0.0473 (4) | |
N1 | 0.92169 (10) | 0.23108 (14) | 0.20414 (15) | 0.0483 (4) | |
O1 | 1.22019 (10) | 0.15475 (13) | −0.06744 (16) | 0.0771 (5) | |
O2 | 0.97921 (8) | 0.06501 (12) | 0.31030 (13) | 0.0609 (4) | |
O3 | 0.67178 (9) | 0.47970 (11) | 0.12780 (12) | 0.0582 (4) | |
O4 | 0.53704 (9) | 0.51746 (12) | 0.23501 (15) | 0.0699 (4) | |
O5 | 0.51735 (10) | 0.38125 (13) | 0.43079 (14) | 0.0729 (4) | |
O6 | 0.89533 (9) | 0.42585 (12) | 0.02007 (13) | 0.0578 (4) | |
H1 | 0.9222 (11) | 0.2829 (13) | 0.1455 (13) | 0.051 (5)* | |
H6A | 0.9271 (12) | 0.4808 (15) | 0.0652 (18) | 0.076* | |
H6B | 0.9070 (14) | 0.417 (2) | −0.0528 (13) | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0936 (19) | 0.0836 (18) | 0.1047 (19) | 0.0148 (14) | 0.0550 (16) | 0.0022 (15) |
C2 | 0.0486 (11) | 0.0563 (13) | 0.0610 (12) | 0.0044 (9) | 0.0182 (10) | 0.0093 (10) |
C3 | 0.0633 (14) | 0.0437 (11) | 0.0948 (16) | 0.0003 (10) | 0.0341 (12) | 0.0114 (11) |
C4 | 0.0572 (12) | 0.0415 (11) | 0.0798 (14) | 0.0042 (9) | 0.0252 (11) | 0.0023 (10) |
C5 | 0.0427 (10) | 0.0435 (10) | 0.0459 (10) | 0.0040 (8) | 0.0076 (8) | 0.0055 (8) |
C6 | 0.0474 (11) | 0.0412 (10) | 0.0490 (10) | 0.0014 (8) | 0.0058 (9) | 0.0077 (8) |
C7 | 0.0517 (12) | 0.0439 (11) | 0.0533 (11) | 0.0069 (9) | 0.0092 (9) | 0.0020 (9) |
C8 | 0.0500 (11) | 0.0440 (10) | 0.0453 (10) | 0.0018 (9) | 0.0069 (9) | 0.0025 (9) |
C9 | 0.0482 (11) | 0.0444 (10) | 0.0370 (9) | −0.0022 (8) | 0.0056 (8) | 0.0016 (8) |
C10 | 0.0429 (10) | 0.0391 (9) | 0.0359 (9) | −0.0022 (8) | 0.0047 (7) | 0.0006 (8) |
C11 | 0.0525 (11) | 0.0402 (10) | 0.0356 (9) | 0.0003 (8) | 0.0066 (8) | 0.0016 (8) |
C12 | 0.0597 (13) | 0.0402 (10) | 0.0477 (10) | 0.0121 (9) | 0.0112 (9) | 0.0041 (9) |
C13 | 0.0547 (12) | 0.0516 (11) | 0.0477 (11) | 0.0070 (9) | 0.0169 (9) | −0.0020 (9) |
C14 | 0.0599 (12) | 0.0486 (11) | 0.0447 (10) | 0.0027 (9) | 0.0129 (9) | 0.0086 (9) |
C15 | 0.0489 (11) | 0.0436 (10) | 0.0452 (10) | 0.0045 (8) | 0.0069 (8) | 0.0059 (9) |
C16 | 0.0892 (18) | 0.0592 (14) | 0.0907 (17) | −0.0149 (12) | 0.0019 (14) | 0.0268 (13) |
C17 | 0.0813 (19) | 0.099 (2) | 0.103 (2) | 0.0370 (15) | −0.0102 (16) | 0.0022 (16) |
C18 | 0.1019 (19) | 0.0920 (18) | 0.0959 (18) | 0.0139 (16) | 0.0632 (16) | 0.0193 (15) |
N2 | 0.0458 (9) | 0.0488 (9) | 0.0476 (8) | 0.0028 (7) | 0.0125 (7) | 0.0042 (7) |
N1 | 0.0503 (10) | 0.0473 (9) | 0.0489 (9) | 0.0064 (7) | 0.0155 (7) | 0.0119 (8) |
O1 | 0.0806 (11) | 0.0649 (10) | 0.1004 (12) | 0.0059 (8) | 0.0497 (9) | 0.0103 (9) |
O2 | 0.0664 (9) | 0.0581 (8) | 0.0600 (8) | 0.0134 (7) | 0.0195 (7) | 0.0202 (7) |
O3 | 0.0713 (9) | 0.0526 (8) | 0.0499 (8) | 0.0039 (7) | 0.0141 (6) | 0.0169 (6) |
O4 | 0.0737 (11) | 0.0588 (9) | 0.0795 (10) | 0.0268 (8) | 0.0236 (8) | 0.0181 (7) |
O5 | 0.0831 (11) | 0.0767 (10) | 0.0708 (9) | 0.0247 (8) | 0.0414 (8) | 0.0134 (8) |
O6 | 0.0684 (10) | 0.0563 (9) | 0.0507 (8) | −0.0118 (7) | 0.0189 (7) | −0.0035 (7) |
Geometric parameters (Å, º) top
C1—O1 | 1.422 (3) | C11—C12 | 1.379 (3) |
C1—H1A | 0.9600 | C12—O4 | 1.376 (2) |
C1—H1B | 0.9600 | C12—C13 | 1.389 (3) |
C1—H1C | 0.9600 | C13—O5 | 1.353 (2) |
C2—O1 | 1.359 (2) | C13—C14 | 1.387 (2) |
C2—C7 | 1.383 (3) | C14—C15 | 1.366 (2) |
C2—C3 | 1.388 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.361 (3) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—O3 | 1.422 (2) |
C4—C5 | 1.392 (3) | C16—H16A | 0.9600 |
C4—H4 | 0.9300 | C16—H16B | 0.9600 |
C5—C6 | 1.379 (2) | C16—H16C | 0.9600 |
C5—C8 | 1.474 (3) | C17—O4 | 1.418 (3) |
C6—C7 | 1.380 (3) | C17—H17A | 0.9600 |
C6—H6 | 0.9300 | C17—H17B | 0.9600 |
C7—H7 | 0.9300 | C17—H17C | 0.9600 |
C8—O2 | 1.236 (2) | C18—O5 | 1.420 (3) |
C8—N1 | 1.350 (2) | C18—H18A | 0.9600 |
C9—N2 | 1.277 (2) | C18—H18B | 0.9600 |
C9—C10 | 1.447 (2) | C18—H18C | 0.9600 |
C9—H9 | 0.9300 | N2—N1 | 1.376 (2) |
C10—C15 | 1.383 (2) | N1—H1 | 0.859 (9) |
C10—C11 | 1.404 (2) | O6—H6A | 0.865 (9) |
C11—O3 | 1.372 (2) | O6—H6B | 0.858 (9) |
| | | |
O1—C1—H1A | 109.5 | C11—C12—C13 | 120.19 (16) |
O1—C1—H1B | 109.5 | O5—C13—C14 | 124.80 (18) |
H1A—C1—H1B | 109.5 | O5—C13—C12 | 116.09 (16) |
O1—C1—H1C | 109.5 | C14—C13—C12 | 119.11 (19) |
H1A—C1—H1C | 109.5 | C15—C14—C13 | 120.29 (17) |
H1B—C1—H1C | 109.5 | C15—C14—H14 | 119.9 |
O1—C2—C7 | 124.14 (18) | C13—C14—H14 | 119.9 |
O1—C2—C3 | 116.16 (18) | C14—C15—C10 | 121.95 (16) |
C7—C2—C3 | 119.7 (2) | C14—C15—H15 | 119.0 |
C4—C3—C2 | 120.54 (19) | C10—C15—H15 | 119.0 |
C4—C3—H3 | 119.7 | O3—C16—H16A | 109.5 |
C2—C3—H3 | 119.7 | O3—C16—H16B | 109.5 |
C3—C4—C5 | 120.87 (18) | H16A—C16—H16B | 109.5 |
C3—C4—H4 | 119.6 | O3—C16—H16C | 109.5 |
C5—C4—H4 | 119.6 | H16A—C16—H16C | 109.5 |
C6—C5—C4 | 117.90 (18) | H16B—C16—H16C | 109.5 |
C6—C5—C8 | 118.71 (16) | O4—C17—H17A | 109.5 |
C4—C5—C8 | 123.33 (17) | O4—C17—H17B | 109.5 |
C5—C6—C7 | 122.08 (17) | H17A—C17—H17B | 109.5 |
C5—C6—H6 | 119.0 | O4—C17—H17C | 109.5 |
C7—C6—H6 | 119.0 | H17A—C17—H17C | 109.5 |
C6—C7—C2 | 118.87 (18) | H17B—C17—H17C | 109.5 |
C6—C7—H7 | 120.6 | O5—C18—H18A | 109.5 |
C2—C7—H7 | 120.6 | O5—C18—H18B | 109.5 |
O2—C8—N1 | 121.41 (19) | H18A—C18—H18B | 109.5 |
O2—C8—C5 | 122.99 (17) | O5—C18—H18C | 109.5 |
N1—C8—C5 | 115.55 (16) | H18A—C18—H18C | 109.5 |
N2—C9—C10 | 121.17 (16) | H18B—C18—H18C | 109.5 |
N2—C9—H9 | 119.4 | C9—N2—N1 | 114.68 (15) |
C10—C9—H9 | 119.4 | C8—N1—N2 | 119.82 (16) |
C15—C10—C11 | 117.60 (17) | C8—N1—H1 | 120.5 (12) |
C15—C10—C9 | 123.02 (16) | N2—N1—H1 | 119.6 (12) |
C11—C10—C9 | 119.39 (16) | C2—O1—C1 | 118.76 (17) |
O3—C11—C12 | 120.08 (16) | C11—O3—C16 | 116.04 (15) |
O3—C11—C10 | 118.94 (17) | C12—O4—C17 | 116.03 (16) |
C12—C11—C10 | 120.84 (16) | C13—O5—C18 | 118.47 (17) |
O4—C12—C11 | 119.17 (17) | H6A—O6—H6B | 111 (2) |
O4—C12—C13 | 120.61 (18) | | |
| | | |
O1—C2—C3—C4 | 179.10 (18) | C10—C11—C12—C13 | 1.1 (3) |
C7—C2—C3—C4 | −2.0 (3) | O4—C12—C13—O5 | 0.1 (3) |
C2—C3—C4—C5 | 1.1 (3) | C11—C12—C13—O5 | 178.15 (16) |
C3—C4—C5—C6 | 0.8 (3) | O4—C12—C13—C14 | −179.95 (16) |
C3—C4—C5—C8 | −176.64 (17) | C11—C12—C13—C14 | −1.9 (3) |
C4—C5—C6—C7 | −1.9 (3) | O5—C13—C14—C15 | −178.97 (17) |
C8—C5—C6—C7 | 175.68 (16) | C12—C13—C14—C15 | 1.1 (3) |
C5—C6—C7—C2 | 1.0 (3) | C13—C14—C15—C10 | 0.6 (3) |
O1—C2—C7—C6 | 179.75 (17) | C11—C10—C15—C14 | −1.4 (2) |
C3—C2—C7—C6 | 1.0 (3) | C9—C10—C15—C14 | 178.98 (16) |
C6—C5—C8—O2 | 34.9 (2) | C10—C9—N2—N1 | −179.79 (14) |
C4—C5—C8—O2 | −147.69 (19) | O2—C8—N1—N2 | 1.2 (3) |
C6—C5—C8—N1 | −142.51 (16) | C5—C8—N1—N2 | 178.68 (14) |
C4—C5—C8—N1 | 34.9 (2) | C9—N2—N1—C8 | −173.92 (15) |
N2—C9—C10—C15 | −0.9 (2) | C7—C2—O1—C1 | 6.8 (3) |
N2—C9—C10—C11 | 179.46 (16) | C3—C2—O1—C1 | −174.4 (2) |
C15—C10—C11—O3 | −175.04 (14) | C12—C11—O3—C16 | 75.4 (2) |
C9—C10—C11—O3 | 4.6 (2) | C10—C11—O3—C16 | −108.9 (2) |
C15—C10—C11—C12 | 0.6 (2) | C11—C12—O4—C17 | 114.9 (2) |
C9—C10—C11—C12 | −179.80 (15) | C13—C12—O4—C17 | −67.1 (2) |
O3—C11—C12—O4 | −5.3 (3) | C14—C13—O5—C18 | −1.5 (3) |
C10—C11—C12—O4 | 179.15 (15) | C12—C13—O5—C18 | 178.49 (19) |
O3—C11—C12—C13 | 176.63 (16) | | |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C2–C7
and C10–C15 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.86 (1) | 2.07 (1) | 2.905 (2) | 164 (2) |
C9—H9···O6 | 0.93 | 2.45 | 3.258 (2) | 146 |
O6—H6A···O2i | 0.87 (1) | 1.98 (1) | 2.8204 (18) | 163 (2) |
O6—H6B···O2ii | 0.86 (1) | 2.11 (1) | 2.914 (2) | 156 (2) |
O6—H6B···N2ii | 0.86 (1) | 2.54 (2) | 3.1880 (19) | 133 (2) |
C1—H1C···Cg2iii | 0.96 | 2.95 | 3.900 (3) | 171 |
C16—H16C···Cg1i | 0.96 | 2.79 | 3.713 (2) | 162 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −z+1/2. |