Crystal structure, DFT and Hirshfeld surface analysis of (E)-N′-[(1-chloro-3,4-di­hydro­naph­thal­en-2-yl)methyl­idene]benzohydrazide monohydrate

In the title compound, C₁₈H₁₅ClN₂O·H₂O, the dihedral angle between the mean plane of the di­hydro­naphthalene ring system and the phenyl ring is 17.1 (2)°. In the crystal, mol­ecules are linked by O—H...O, N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 301 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.151
• Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00574 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.384 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   5 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

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-N'-[(1-Chloro-3,4-dihydronaphthalen-2-yl)methylidene]\ benzohydrazide monohydrate

Crystal data

C18H15ClN2O·H2O	F(000) = 688
Mr = 328.78	Dx = 1.352 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 689 reflections
a = 26.2059 (18) Å	θ = 2.2–30.1°
b = 4.8119 (3) Å	µ = 0.25 mm^−1
c = 12.8084 (9) Å	T = 301 K
V = 1615.14 (19) Å^3	Block, white
Z = 4	0.28 × 0.22 × 0.21 mm

Data collection

Bruker APEXII microsource diffractometer	4917 independent reflections
Radiation source: microfocus sealed X-ray tube	3162 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.069
Detector resolution: 7.9 pixels mm^-1	θmax = 30.6°, θmin = 2.2°
ω and φ scans	h = −37→36
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −6→6
Tmin = 0.890, Tmax = 0.915	l = −18→18
51179 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0735P)^2 + 0.2866P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4917 reflections	Δρmax = 0.18 e Å^−3
220 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack x determined using 1242 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl01	0.64431 (5)	0.3485 (3)	0.24491 (8)	0.0815 (4)
O1	0.48097 (11)	−0.3470 (5)	0.58021 (18)	0.0577 (6)
O2	0.48890 (14)	0.1565 (7)	0.6974 (2)	0.0676 (8)
N6	0.50596 (11)	−0.2027 (6)	0.4205 (2)	0.0463 (6)
N2	0.54124 (11)	−0.0257 (5)	0.4646 (2)	0.0469 (6)
C1	0.44073 (17)	−0.6214 (7)	0.3284 (3)	0.0589 (9)
H1	0.464242	−0.537211	0.284202	0.071*
C2	0.40586 (19)	−0.8116 (8)	0.2890 (3)	0.0699 (11)
H2	0.405810	−0.852699	0.218085	0.084*
C3	0.37164 (16)	−0.9389 (9)	0.3536 (4)	0.0677 (11)
H3	0.348710	−1.067883	0.326756	0.081*
C4	0.37102 (15)	−0.8766 (9)	0.4583 (4)	0.0661 (10)
H4	0.347389	−0.961795	0.501996	0.079*
C5	0.40541 (13)	−0.6878 (8)	0.4987 (3)	0.0543 (8)
H5	0.405023	−0.648210	0.569795	0.065*
C6	0.44038 (12)	−0.5569 (6)	0.4347 (2)	0.0440 (7)
C7	0.47695 (12)	−0.3606 (6)	0.4845 (2)	0.0429 (6)
C8	0.57029 (13)	0.1000 (8)	0.3996 (3)	0.0514 (8)
H8	0.566552	0.073299	0.328142	0.062*
C9	0.60942 (13)	0.2864 (7)	0.4405 (3)	0.0500 (7)
C10	0.61014 (14)	0.3515 (8)	0.5571 (3)	0.0546 (8)
H10A	0.593193	0.203807	0.595282	0.066*
H10B	0.591853	0.523334	0.570138	0.066*
C11	0.66436 (15)	0.3790 (9)	0.5944 (3)	0.0603 (9)
H11A	0.664204	0.450456	0.665242	0.072*
H11B	0.679939	0.196212	0.595934	0.072*
C12	0.69626 (13)	0.5672 (8)	0.5273 (3)	0.0548 (8)
C13	0.73640 (15)	0.7232 (10)	0.5674 (4)	0.0703 (11)
H13	0.743717	0.714146	0.638323	0.084*
C14	0.76533 (16)	0.8898 (10)	0.5042 (5)	0.0796 (14)
H14	0.791894	0.993296	0.532615	0.096*
C15	0.75553 (16)	0.9049 (10)	0.4007 (5)	0.0771 (13)
H15	0.775202	1.020496	0.358664	0.093*
C16	0.71653 (16)	0.7501 (10)	0.3565 (4)	0.0692 (11)
H16	0.710430	0.759136	0.285089	0.083*
C17	0.68627 (13)	0.5795 (8)	0.4204 (3)	0.0549 (8)
C18	0.64461 (13)	0.4061 (8)	0.3791 (3)	0.0536 (8)
H2A	0.4899 (19)	0.281 (11)	0.658 (4)	0.068 (14)*
H2B	0.4887 (19)	−0.005 (13)	0.653 (4)	0.082 (15)*
H6	0.4993 (18)	−0.204 (10)	0.349 (4)	0.071 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0854 (7)	0.1131 (10)	0.0460 (5)	−0.0167 (6)	0.0052 (5)	0.0096 (6)
O1	0.0824 (17)	0.0516 (13)	0.0391 (11)	−0.0173 (12)	−0.0005 (11)	0.0002 (10)
O2	0.107 (2)	0.0580 (17)	0.0377 (12)	−0.0104 (15)	−0.0058 (13)	0.0033 (13)
N6	0.0548 (15)	0.0444 (14)	0.0396 (13)	−0.0079 (12)	−0.0029 (12)	0.0010 (11)
N2	0.0532 (15)	0.0418 (13)	0.0456 (13)	−0.0061 (11)	−0.0046 (11)	0.0014 (11)
C1	0.082 (2)	0.0491 (19)	0.0460 (18)	−0.0105 (17)	−0.0023 (17)	−0.0016 (15)
C2	0.099 (3)	0.056 (2)	0.054 (2)	−0.009 (2)	−0.017 (2)	−0.0074 (18)
C3	0.063 (2)	0.052 (2)	0.088 (3)	−0.0062 (18)	−0.016 (2)	−0.009 (2)
C4	0.051 (2)	0.063 (2)	0.085 (3)	−0.0085 (17)	0.0055 (19)	−0.004 (2)
C5	0.0508 (18)	0.0550 (19)	0.057 (2)	−0.0037 (15)	0.0072 (15)	−0.0048 (16)
C6	0.0511 (17)	0.0363 (13)	0.0445 (15)	0.0031 (12)	−0.0035 (13)	−0.0007 (12)
C7	0.0513 (16)	0.0380 (14)	0.0393 (15)	0.0017 (12)	−0.0007 (12)	0.0007 (12)
C8	0.0556 (18)	0.0532 (18)	0.0454 (17)	−0.0059 (15)	0.0009 (14)	0.0022 (14)
C9	0.0533 (18)	0.0493 (17)	0.0475 (18)	0.0011 (14)	0.0012 (14)	0.0040 (14)
C10	0.0507 (17)	0.064 (2)	0.0495 (18)	−0.0105 (16)	0.0004 (14)	−0.0084 (15)
C11	0.063 (2)	0.064 (2)	0.054 (2)	0.0048 (18)	−0.0070 (17)	0.0023 (17)
C12	0.0467 (17)	0.0496 (17)	0.068 (2)	0.0052 (14)	−0.0017 (16)	−0.0001 (17)
C13	0.055 (2)	0.073 (3)	0.083 (3)	−0.0009 (19)	−0.008 (2)	−0.008 (2)
C14	0.050 (2)	0.072 (3)	0.117 (5)	−0.0076 (19)	−0.003 (2)	−0.001 (3)
C15	0.056 (2)	0.069 (3)	0.107 (4)	−0.009 (2)	0.010 (2)	0.015 (2)
C16	0.062 (2)	0.069 (2)	0.077 (3)	0.0004 (19)	0.009 (2)	0.016 (2)
C17	0.0453 (17)	0.0497 (18)	0.070 (2)	0.0026 (14)	−0.0001 (15)	0.0058 (17)
C18	0.0548 (18)	0.0603 (19)	0.0457 (17)	−0.0032 (15)	0.0027 (15)	0.0074 (16)

Geometric parameters (Å, º)

Cl01—C18	1.741 (4)	C8—H8	0.9300
O1—C7	1.233 (4)	C9—C18	1.342 (5)
O2—H2A	0.79 (6)	C9—C10	1.527 (5)
O2—H2B	0.96 (6)	C10—C11	1.505 (5)
N6—C7	1.352 (4)	C10—H10A	0.9700
N6—N2	1.378 (4)	C10—H10B	0.9700
N6—H6	0.93 (5)	C11—C12	1.502 (6)
N2—C8	1.280 (4)	C11—H11A	0.9700
C1—C2	1.389 (6)	C11—H11B	0.9700
C1—C6	1.396 (5)	C12—C13	1.390 (6)
C1—H1	0.9300	C12—C17	1.396 (5)
C2—C3	1.365 (7)	C13—C14	1.368 (7)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.374 (7)	C14—C15	1.352 (7)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.381 (5)	C15—C16	1.385 (7)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.381 (5)	C16—C17	1.404 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.489 (4)	C17—C18	1.472 (5)
C8—C9	1.459 (5)
H2A—O2—H2B	104 (5)	C9—C10—H10A	109.7
C7—N6—N2	118.4 (3)	C11—C10—H10A	109.7
C7—N6—H6	119 (3)	C9—C10—H10B	109.7
N2—N6—H6	122 (3)	C11—C10—H10B	109.7
C8—N2—N6	115.1 (3)	H10A—C10—H10B	108.2
C2—C1—C6	119.8 (4)	C12—C11—C10	113.4 (3)
C2—C1—H1	120.1	C12—C11—H11A	108.9
C6—C1—H1	120.1	C10—C11—H11A	108.9
C3—C2—C1	120.5 (4)	C12—C11—H11B	108.9
C3—C2—H2	119.7	C10—C11—H11B	108.9
C1—C2—H2	119.7	H11A—C11—H11B	107.7
C4—C3—C2	120.1 (4)	C13—C12—C17	118.7 (4)
C4—C3—H3	120.0	C13—C12—C11	122.4 (4)
C2—C3—H3	120.0	C17—C12—C11	118.9 (3)
C3—C4—C5	120.1 (4)	C14—C13—C12	121.2 (5)
C3—C4—H4	119.9	C14—C13—H13	119.4
C5—C4—H4	119.9	C12—C13—H13	119.4
C6—C5—C4	120.7 (4)	C13—C14—C15	120.4 (4)
C6—C5—H5	119.7	C13—C14—H14	119.8
C4—C5—H5	119.7	C15—C14—H14	119.8
C5—C6—C1	118.8 (3)	C14—C15—C16	120.8 (4)
C5—C6—C7	117.5 (3)	C14—C15—H15	119.6
C1—C6—C7	123.6 (3)	C16—C15—H15	119.6
O1—C7—N6	121.7 (3)	C15—C16—C17	119.6 (4)
O1—C7—C6	121.0 (3)	C15—C16—H16	120.2
N6—C7—C6	117.3 (3)	C17—C16—H16	120.2
N2—C8—C9	118.4 (3)	C16—C17—C12	119.4 (4)
N2—C8—H8	120.8	C16—C17—C18	122.8 (4)
C9—C8—H8	120.8	C12—C17—C18	117.9 (3)
C18—C9—C8	122.4 (3)	C9—C18—C17	122.8 (3)
C18—C9—C10	118.5 (3)	C9—C18—Cl01	120.5 (3)
C8—C9—C10	119.1 (3)	C17—C18—Cl01	116.6 (3)
C9—C10—C11	109.9 (3)
C7—N6—N2—C8	174.4 (3)	C10—C11—C12—C13	149.3 (4)
C6—C1—C2—C3	−0.8 (6)	C10—C11—C12—C17	−32.7 (5)
C1—C2—C3—C4	0.9 (7)	C17—C12—C13—C14	1.0 (6)
C2—C3—C4—C5	−0.8 (6)	C11—C12—C13—C14	179.0 (4)
C3—C4—C5—C6	0.7 (6)	C12—C13—C14—C15	−0.4 (7)
C4—C5—C6—C1	−0.7 (5)	C13—C14—C15—C16	−0.7 (8)
C4—C5—C6—C7	−178.7 (3)	C14—C15—C16—C17	1.1 (7)
C2—C1—C6—C5	0.8 (5)	C15—C16—C17—C12	−0.5 (6)
C2—C1—C6—C7	178.6 (3)	C15—C16—C17—C18	−179.1 (4)
N2—N6—C7—O1	0.9 (5)	C13—C12—C17—C16	−0.6 (5)
N2—N6—C7—C6	−178.0 (3)	C11—C12—C17—C16	−178.7 (4)
C5—C6—C7—O1	10.7 (5)	C13—C12—C17—C18	178.2 (4)
C1—C6—C7—O1	−167.2 (3)	C11—C12—C17—C18	0.1 (5)
C5—C6—C7—N6	−170.5 (3)	C8—C9—C18—C17	−175.8 (3)
C1—C6—C7—N6	11.6 (5)	C10—C9—C18—C17	5.0 (5)
N6—N2—C8—C9	−178.7 (3)	C8—C9—C18—Cl01	1.3 (5)
N2—C8—C9—C18	173.5 (3)	C10—C9—C18—Cl01	−177.9 (3)
N2—C8—C9—C10	−7.3 (5)	C16—C17—C18—C9	−166.5 (4)
C18—C9—C10—C11	−36.7 (5)	C12—C17—C18—C9	14.8 (5)
C8—C9—C10—C11	144.1 (3)	C16—C17—C18—Cl01	16.3 (5)
C9—C10—C11—C12	49.2 (5)	C12—C17—C18—Cl01	−162.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	0.78 (5)	2.06 (5)	2.829 (4)	166 (5)
O2—H2B···O1	0.96 (6)	1.90 (6)	2.858 (4)	171 (5)
N6—H6···O2^ii	0.93 (5)	1.98 (5)	2.869 (4)	159 (4)
C1—H1···O2^ii	0.93	2.47	3.350 (5)	158
C8—H8···O2^ii	0.93	2.48	3.261 (5)	142

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, z−1/2.