N′-[(E)-4-(Diethyl­amino)benzyl­idene]-4-nitro­benzohydrazide monohydrate

Ahmad, T.; Zia-ur-Rehman, M.; Siddiqui, H.L.; Rizvi, S.U.F.; Parvez, M.

doi:10.1107/S1600536810011554

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o1007-o1008

doi:10.1107/S1600536810011554

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N′-[(E)-4-(Diethylamino)benzylidene]-4-nitrobenzohydrazide monohydrate

Tanveer Ahmad,^a Muhammad Zia-ur-Rehman,^b ^* Hamid Latif Siddiqui,^a Syed Umar Farooq Rizvi ^a and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: rehman_pcsir@hotmail.com

(Received 25 March 2010; accepted 26 March 2010; online 31 March 2010)

In the title compound, C₁₈H₂₀N₄O₃·H₂O, the two aromatic rings are linked through a methylidenehydrazide fragment, which is fully extended with C—C—N—N, C—N—N=C and N—N=C—C torsion angles of 179.4 (2), 174.7 (2) and 178.3 (2)°, respectively. The dihedral angle between the two aromatic rings is 7.01 (8)°. In the crystal structure, the water of hydration is involved in extensive hydrogen bonding. Intermolecular O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds link the components of the structure into a two-dimensional network and additional stabilization is provided by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis of related compounds, see: Ahmad et al. (2010 ). For the coordinating capability of hydrazones, see: Rodríguez-Argüelles et al. (2004 ). For the biological activity of benzohydrazides, see: Zia-ur-Rehman et al. (2009 ); Galal et al. (2009 ); Bordoloi et al. (2009 ). For closely related structures, see: Fun et al. (2008 ); Bessy et al. (2006 ).

Experimental

Crystal data

C₁₈H₂₀N₄O₃·H₂O
M_r = 358.40
Monoclinic, C 2/c
a = 38.3142 (12) Å
b = 7.4563 (3) Å
c = 12.6332 (5) Å
β = 98.215 (2)°
V = 3572.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.08 × 0.06 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.992, T_max = 0.996
5710 measured reflections
4048 independent reflections
3182 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.138
S = 1.11
4048 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯O3ⁱ	0.83 (4)	2.23 (4)	3.009 (3)	156 (3)
N2—H2N⋯O4	0.88 (2)	2.00 (2)	2.861 (2)	165 (2)
O4—H4A⋯O3ⁱⁱ	0.85 (3)	2.06 (4)	2.823 (2)	149 (3)
O4—H4A⋯N3ⁱⁱ	0.85 (3)	2.57 (3)	3.250 (3)	138 (3)
C5—H5⋯O3ⁱⁱ	0.95	2.54	3.308 (2)	138
C8—H8⋯O4	0.95	2.50	3.270 (3)	138
C13—H13⋯O2ⁱⁱⁱ	0.95	2.51	3.350 (3)	148
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011554/bt5231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011554/bt5231Isup2.hkl

checkCIF report

Comment top

The chemistry of hydrazones is being investigated continuously due to their excellent coordinating capability (Rodríguez-Argüelles et al., 2004) and biological activities (Zia-ur-Rehman et al., 2009; Galal et al., 2009; Bordoloi et al., 2009). In continuation of our studies on the synthesis of various heterocyclic compounds (Ahmad et al., 2010), the title compound, (I), has been synthesized and its crystal structure determined by X-ray crystallographic method which is presented in this article.

In the the title compound (Fig. 1) the bond distances and angles agree with the corresponding bond distances and angles reported in closely related compounds (Fun et al., 2008; Bessy et al., 2006). The benzene rings in (I) are linked through a methylidenehydrazide fragment, C6/C7/N2/N3/C8, which is fully extended with torsion angles C6–C7–N2–N3, C7–N2–N3\ C8 and N2–N3═C8–C9 179.4 (2), 174.7 (2) and 178.3 (2)°, respectively. The dihedral angle between the two benzene rings is 7.01 (8)°. In the crystal structure, the water of hydration is extensively involved in hydrogen bonding. Thus, intermolecular O—H···O, N—H···O and O—H···N hydrogen bonds link the components of the structure into a two-dimensional network and additional stabilization is provided by weak intermolecular C—H···O hydrogen bonds; details have been provided in Table. 1. and Fig. 2.

Related literature top

For the synthesis of related compounds, see: Ahmad et al. (2010). For the coordinating capability of hydrazones, see: Rodríguez-Argüelles et al. (2004). For the biological activity of benzohydrazides, see: Zia-ur-Rehman et al. (2009); Galal et al. (2009); Bordoloi et al. (2009). For closely related structures, see: Fun et al. (2008); Bessy et al. (2006).

Experimental top

A mixture of para nitrobenzohydrazide (0.5 g, 2.76 mmoles), p-(diethylamino)benzaldehyde (0.49 g, 2.76 mmoles), orthophosphoric acid (0.2 ml) and methanol (50.0 ml) was refluxed for a period of 5.5 hours followed by removal of the solvent under vacuum. The contents were cooled and washed with cold methanol followed by crystallization from the same solvent at room temperature by slow evaporation. Yield: 91%. M.p. 491 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title compound with the displacement ellipsoids plotted at 50% probability level (Farrugia, 1997). Symmetry code ^* = x, 1-y, z+1/2.
	Fig. 2. The unit cell packing of the title compound; H-bonds have been plotted with dashed lines and H-atoms not involved in H-bonds have been excluded for clarity.

N'-[(E)-4-(Diethylamino)benzylidene]-4-nitrobenzohydrazide monohydrate top

Crystal data top

C₁₈H₂₀N₄O₃·H₂O	F(000) = 1520
M_r = 358.40	D_x = 1.333 Mg m⁻³
Monoclinic, C2/c	Melting point: 491 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.3142 (12) Å	Cell parameters from 3855 reflections
b = 7.4563 (3) Å	θ = 1.0–27.5°
c = 12.6332 (5) Å	µ = 0.10 mm⁻¹
β = 98.215 (2)°	T = 173 K
V = 3572.0 (2) Å³	Prism, orange
Z = 8	0.08 × 0.06 × 0.04 mm

Data collection top

Nonius KappaCCD diffractometer	4048 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −49→49
T_min = 0.992, T_max = 0.996	k = −6→9
5710 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: difference Fourier map
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0299P)² + 6.8806P] where P = (F_o² + 2F_c²)/3
4048 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₂₀N₄O₃·H₂O	V = 3572.0 (2) Å³
M_r = 358.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.3142 (12) Å	µ = 0.10 mm⁻¹
b = 7.4563 (3) Å	T = 173 K
c = 12.6332 (5) Å	0.08 × 0.06 × 0.04 mm
β = 98.215 (2)°

Data collection top

Nonius KappaCCD diffractometer	4048 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3182 reflections with I > 2σ(I)
T_min = 0.992, T_max = 0.996	R_int = 0.021
5710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.29 e Å⁻³
4048 reflections	Δρ_min = −0.19 e Å⁻³
246 parameters

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.

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

	x	y	z	U_iso*/U_eq
O4	0.24370 (5)	0.6548 (3)	0.29158 (14)	0.0491 (5)
H4A	0.2524 (8)	0.625 (5)	0.236 (3)	0.074*
H4B	0.2376 (9)	0.762 (5)	0.289 (3)	0.074*
O1	0.44265 (4)	0.7990 (3)	0.48843 (14)	0.0504 (5)
O2	0.42219 (4)	0.7098 (3)	0.32907 (14)	0.0529 (5)
O3	0.29243 (4)	0.4979 (3)	0.66984 (12)	0.0470 (5)
N1	0.41920 (5)	0.7349 (3)	0.42338 (15)	0.0382 (4)
N2	0.26157 (4)	0.5178 (2)	0.50392 (14)	0.0309 (4)
H2N	0.2601 (6)	0.555 (3)	0.4374 (19)	0.037*
N3	0.23060 (4)	0.4687 (2)	0.54236 (14)	0.0329 (4)
N4	0.06636 (4)	0.2626 (3)	0.54414 (14)	0.0385 (5)
C1	0.35196 (5)	0.6469 (3)	0.60129 (16)	0.0360 (5)
H1	0.3497	0.6546	0.6750	0.043*
C2	0.38313 (5)	0.6981 (3)	0.56723 (17)	0.0376 (5)
H2	0.4023	0.7423	0.6165	0.045*
C3	0.38577 (5)	0.6834 (3)	0.45998 (16)	0.0317 (4)
C4	0.35855 (5)	0.6218 (3)	0.38607 (16)	0.0355 (5)
H4	0.3611	0.6134	0.3125	0.043*
C5	0.32730 (5)	0.5720 (3)	0.42139 (16)	0.0331 (5)
H5	0.3081	0.5294	0.3716	0.040*
C6	0.32385 (5)	0.5841 (3)	0.52888 (15)	0.0286 (4)
C7	0.29128 (5)	0.5290 (3)	0.57364 (16)	0.0308 (4)
C8	0.20420 (5)	0.4474 (3)	0.46932 (17)	0.0330 (4)
H8	0.2075	0.4627	0.3968	0.040*
C9	0.16922 (5)	0.4008 (3)	0.49284 (16)	0.0313 (4)
C10	0.16034 (5)	0.3932 (3)	0.59596 (16)	0.0324 (5)
H10	0.1778	0.4189	0.6553	0.039*
C11	0.12662 (5)	0.3491 (3)	0.61358 (16)	0.0327 (5)
H11	0.1213	0.3454	0.6847	0.039*
C12	0.09998 (5)	0.3094 (3)	0.52795 (16)	0.0326 (5)
C13	0.10887 (5)	0.3192 (3)	0.42407 (17)	0.0371 (5)
H13	0.0915	0.2945	0.3644	0.044*
C14	0.14265 (6)	0.3645 (3)	0.40804 (17)	0.0373 (5)
H14	0.1480	0.3711	0.3370	0.045*
C15	0.05774 (6)	0.2167 (3)	0.64950 (17)	0.0387 (5)
H15A	0.0788	0.1621	0.6922	0.046*
H15B	0.0388	0.1253	0.6410	0.046*
C16	0.04582 (6)	0.3745 (4)	0.7111 (2)	0.0502 (6)
H16A	0.0392	0.3322	0.7789	0.075*
H16B	0.0255	0.4321	0.6686	0.075*
H16C	0.0651	0.4613	0.7256	0.075*
C17	0.03658 (6)	0.2743 (4)	0.45771 (18)	0.0449 (6)
H17A	0.0415	0.3697	0.4073	0.054*
H17B	0.0152	0.3095	0.4884	0.054*
C18	0.02924 (7)	0.1007 (4)	0.3964 (2)	0.0595 (8)
H18A	0.0493	0.0714	0.3595	0.089*
H18B	0.0080	0.1144	0.3438	0.089*
H18C	0.0257	0.0040	0.4463	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0535 (10)	0.0650 (12)	0.0311 (8)	0.0156 (9)	0.0143 (7)	0.0043 (9)
O1	0.0315 (8)	0.0661 (12)	0.0534 (10)	−0.0138 (8)	0.0055 (7)	0.0024 (9)
O2	0.0483 (10)	0.0704 (13)	0.0443 (9)	−0.0106 (9)	0.0216 (8)	0.0001 (9)
O3	0.0312 (8)	0.0813 (13)	0.0286 (7)	−0.0081 (8)	0.0043 (6)	0.0116 (8)
N1	0.0316 (9)	0.0399 (11)	0.0443 (10)	−0.0039 (8)	0.0098 (8)	0.0046 (9)
N2	0.0241 (8)	0.0398 (10)	0.0297 (8)	−0.0028 (7)	0.0063 (7)	0.0027 (8)
N3	0.0241 (8)	0.0379 (10)	0.0376 (9)	−0.0030 (7)	0.0072 (7)	0.0018 (8)
N4	0.0248 (8)	0.0575 (13)	0.0325 (9)	−0.0085 (8)	0.0011 (7)	0.0024 (9)
C1	0.0307 (10)	0.0519 (14)	0.0248 (9)	−0.0055 (10)	0.0017 (8)	0.0008 (9)
C2	0.0286 (10)	0.0512 (14)	0.0317 (10)	−0.0083 (10)	0.0002 (8)	−0.0005 (10)
C3	0.0261 (9)	0.0335 (11)	0.0359 (10)	−0.0018 (8)	0.0062 (8)	0.0034 (9)
C4	0.0333 (11)	0.0469 (13)	0.0270 (10)	−0.0019 (9)	0.0071 (8)	−0.0027 (9)
C5	0.0282 (10)	0.0419 (12)	0.0287 (10)	−0.0041 (9)	0.0023 (8)	−0.0033 (9)
C6	0.0258 (9)	0.0313 (10)	0.0290 (9)	−0.0006 (8)	0.0049 (8)	0.0010 (8)
C7	0.0287 (10)	0.0354 (11)	0.0289 (10)	−0.0029 (8)	0.0061 (8)	0.0009 (8)
C8	0.0294 (10)	0.0361 (11)	0.0343 (10)	−0.0021 (9)	0.0075 (8)	0.0009 (9)
C9	0.0249 (9)	0.0347 (11)	0.0340 (10)	−0.0024 (8)	0.0028 (8)	0.0010 (9)
C10	0.0258 (9)	0.0377 (11)	0.0322 (10)	−0.0012 (8)	−0.0006 (8)	−0.0009 (9)
C11	0.0263 (10)	0.0415 (12)	0.0299 (10)	−0.0007 (9)	0.0027 (8)	0.0032 (9)
C12	0.0257 (9)	0.0379 (11)	0.0339 (10)	−0.0035 (8)	0.0028 (8)	0.0025 (9)
C13	0.0291 (10)	0.0489 (13)	0.0314 (10)	−0.0071 (9)	−0.0023 (8)	0.0022 (10)
C14	0.0338 (11)	0.0466 (13)	0.0314 (10)	−0.0067 (10)	0.0047 (9)	−0.0001 (9)
C15	0.0280 (10)	0.0515 (14)	0.0363 (11)	−0.0080 (10)	0.0039 (8)	0.0067 (10)
C16	0.0405 (13)	0.0680 (18)	0.0436 (13)	0.0061 (12)	0.0114 (11)	0.0064 (13)
C17	0.0287 (10)	0.0637 (16)	0.0407 (12)	−0.0069 (11)	−0.0006 (9)	0.0075 (11)
C18	0.0498 (15)	0.080 (2)	0.0464 (14)	−0.0243 (14)	−0.0024 (12)	−0.0023 (14)

Geometric parameters (Å, º) top

O4—H4A	0.85 (3)	C8—C9	1.456 (3)
O4—H4B	0.83 (4)	C8—H8	0.9500
O1—N1	1.225 (2)	C9—C10	1.394 (3)
O2—N1	1.228 (2)	C9—C14	1.395 (3)
O3—C7	1.232 (2)	C10—C11	1.382 (3)
N1—C3	1.473 (3)	C10—H10	0.9500
N2—C7	1.339 (2)	C11—C12	1.409 (3)
N2—N3	1.394 (2)	C11—H11	0.9500
N2—H2N	0.88 (2)	C12—C13	1.404 (3)
N3—C8	1.278 (3)	C13—C14	1.380 (3)
N4—C12	1.378 (3)	C13—H13	0.9500
N4—C15	1.457 (3)	C14—H14	0.9500
N4—C17	1.465 (3)	C15—C16	1.517 (4)
C1—C2	1.380 (3)	C15—H15A	0.9900
C1—C6	1.391 (3)	C15—H15B	0.9900
C1—H1	0.9500	C16—H16A	0.9800
C2—C3	1.377 (3)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.376 (3)	C17—C18	1.514 (4)
C4—C5	1.387 (3)	C17—H17A	0.9900
C4—H4	0.9500	C17—H17B	0.9900
C5—C6	1.386 (3)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.499 (3)	C18—H18C	0.9800

H4A—O4—H4B	111 (3)	C11—C10—H10	119.4
O1—N1—O2	123.34 (19)	C9—C10—H10	119.4
O1—N1—C3	118.57 (18)	C10—C11—C12	121.19 (19)
O2—N1—C3	118.09 (18)	C10—C11—H11	119.4
C7—N2—N3	118.26 (17)	C12—C11—H11	119.4
C7—N2—H2N	122.7 (15)	N4—C12—C13	120.59 (18)
N3—N2—H2N	118.4 (15)	N4—C12—C11	121.96 (19)
C8—N3—N2	113.98 (17)	C13—C12—C11	117.45 (18)
C12—N4—C15	122.27 (17)	C14—C13—C12	120.52 (19)
C12—N4—C17	121.30 (18)	C14—C13—H13	119.7
C15—N4—C17	116.15 (17)	C12—C13—H13	119.7
C2—C1—C6	120.75 (19)	C13—C14—C9	122.1 (2)
C2—C1—H1	119.6	C13—C14—H14	118.9
C6—C1—H1	119.6	C9—C14—H14	118.9
C3—C2—C1	118.25 (19)	N4—C15—C16	114.2 (2)
C3—C2—H2	120.9	N4—C15—H15A	108.7
C1—C2—H2	120.9	C16—C15—H15A	108.7
C4—C3—C2	122.61 (19)	N4—C15—H15B	108.7
C4—C3—N1	118.86 (19)	C16—C15—H15B	108.7
C2—C3—N1	118.52 (18)	H15A—C15—H15B	107.6
C3—C4—C5	118.47 (19)	C15—C16—H16A	109.5
C3—C4—H4	120.8	C15—C16—H16B	109.5
C5—C4—H4	120.8	H16A—C16—H16B	109.5
C6—C5—C4	120.35 (18)	C15—C16—H16C	109.5
C6—C5—H5	119.8	H16A—C16—H16C	109.5
C4—C5—H5	119.8	H16B—C16—H16C	109.5
C5—C6—C1	119.55 (18)	N4—C17—C18	113.5 (2)
C5—C6—C7	123.55 (17)	N4—C17—H17A	108.9
C1—C6—C7	116.88 (18)	C18—C17—H17A	108.9
O3—C7—N2	122.99 (18)	N4—C17—H17B	108.9
O3—C7—C6	120.63 (17)	C18—C17—H17B	108.9
N2—C7—C6	116.38 (17)	H17A—C17—H17B	107.7
N3—C8—C9	122.62 (19)	C17—C18—H18A	109.5
N3—C8—H8	118.7	C17—C18—H18B	109.5
C9—C8—H8	118.7	H18A—C18—H18B	109.5
C10—C9—C14	117.46 (18)	C17—C18—H18C	109.5
C10—C9—C8	123.73 (18)	H18A—C18—H18C	109.5
C14—C9—C8	118.80 (19)	H18B—C18—H18C	109.5
C11—C10—C9	121.26 (18)

C7—N2—N3—C8	−174.7 (2)	N2—N3—C8—C9	−178.3 (2)
C6—C1—C2—C3	−0.7 (4)	N3—C8—C9—C10	6.9 (3)
C1—C2—C3—C4	0.6 (4)	N3—C8—C9—C14	−174.4 (2)
C1—C2—C3—N1	−178.9 (2)	C14—C9—C10—C11	0.8 (3)
O1—N1—C3—C4	176.0 (2)	C8—C9—C10—C11	179.6 (2)
O2—N1—C3—C4	−4.6 (3)	C9—C10—C11—C12	0.2 (3)
O1—N1—C3—C2	−4.4 (3)	C15—N4—C12—C13	167.7 (2)
O2—N1—C3—C2	175.0 (2)	C17—N4—C12—C13	−18.6 (3)
C2—C3—C4—C5	−0.2 (4)	C15—N4—C12—C11	−12.3 (3)
N1—C3—C4—C5	179.4 (2)	C17—N4—C12—C11	161.3 (2)
C3—C4—C5—C6	−0.2 (3)	C10—C11—C12—N4	179.1 (2)
C4—C5—C6—C1	0.1 (3)	C10—C11—C12—C13	−1.0 (3)
C4—C5—C6—C7	−178.5 (2)	N4—C12—C13—C14	−179.4 (2)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—C14	0.6 (3)
C2—C1—C6—C7	179.1 (2)	C12—C13—C14—C9	0.5 (4)
N3—N2—C7—O3	0.1 (3)	C10—C9—C14—C13	−1.2 (3)
N3—N2—C7—C6	−179.4 (2)	C8—C9—C14—C13	179.9 (2)
C5—C6—C7—O3	160.9 (2)	C12—N4—C15—C16	91.3 (3)
C1—C6—C7—O3	−17.8 (3)	C17—N4—C15—C16	−82.7 (3)
C5—C6—C7—N2	−19.6 (3)	C12—N4—C17—C18	93.1 (3)
C1—C6—C7—N2	161.7 (2)	C15—N4—C17—C18	−92.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O3ⁱ	0.83 (4)	2.23 (4)	3.009 (3)	156 (3)
N2—H2N···O4	0.88 (2)	2.00 (2)	2.861 (2)	165 (2)
O4—H4A···O3ⁱⁱ	0.85 (3)	2.06 (4)	2.823 (2)	149 (3)
O4—H4A···N3ⁱⁱ	0.85 (3)	2.57 (3)	3.250 (3)	138 (3)
C5—H5···O3ⁱⁱ	0.95	2.54	3.308 (2)	138
C8—H8···O4	0.95	2.50	3.270 (3)	138
C13—H13···O2ⁱⁱⁱ	0.95	2.51	3.350 (3)	148

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₄O₃·H₂O
M_r	358.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	38.3142 (12), 7.4563 (3), 12.6332 (5)
β (°)	98.215 (2)
V (Å³)	3572.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.992, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	5710, 4048, 3182
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.138, 1.11
No. of reflections	4048
No. of parameters	246
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.19

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O3ⁱ	0.83 (4)	2.23 (4)	3.009 (3)	156 (3)
N2—H2N···O4	0.88 (2)	2.00 (2)	2.861 (2)	165 (2)
O4—H4A···O3ⁱⁱ	0.85 (3)	2.06 (4)	2.823 (2)	149 (3)
O4—H4A···N3ⁱⁱ	0.85 (3)	2.57 (3)	3.250 (3)	138 (3)
C5—H5···O3ⁱⁱ	0.95	2.54	3.308 (2)	138
C8—H8···O4	0.95	2.50	3.270 (3)	138
C13—H13···O2ⁱⁱⁱ	0.95	2.51	3.350 (3)	148

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

HLS is grateful to the Institute of Chemistry, University of the Punjab, for financial support.

References

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