1-[((E)-{2-[(2-Nitro­benz­yl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methyl­idene]aza­nium­yl}eth­yl)amino]­eth­yl}aza­niumyl­idene)meth­yl]naphthalen-2-olate monohydrate

Menati, S.; Amiri Rudbari, H.; Azadbakht, R.; Bruno, G.

doi:10.1107/S1600536811047465

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3321

https://doi.org/10.1107/S1600536811047465

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1-[((E)-{2-[(2-Nitrobenzyl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methylidene]azaniumyl}ethyl)amino]ethyl}azaniumylidene)methyl]naphthalen-2-olate monohydrate

Saeid Menati,^a ^* Hadi Amiri Rudbari,^b Reza Azadbakht ^c and Giuseppe Bruno ^b

^aDepartment of Chemistry, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, ^bDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina 98166 Messina, Italy, and ^cDepartment of Chemistry, Payame Noor University, Hamedan, Iran
^*Correspondence e-mail: s_menati723@yahoo.com

(Received 27 October 2011; accepted 9 November 2011; online 16 November 2011)

The title Schiff base compound, C₃₃H₃₀N₄O₄·H₂O, adopts an E configuration with respect to each C=N double bond. In the molecule, there are naphthoxide anions and the protonated imino N atoms. Intramolecular N—H⋯O hydrogen bonds lead to the formation of approximately planar (maximum deviation 0.029 Å for H atom) six-membered rings.. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds as well as C—H⋯O contacts, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Keypour et al. (2008 ); Zeng et al. (1999 ); McKee et al. (2006 ). For Schiff base derivatives incorporating a fluorescent moiety as tools for optical sensing of metal ions, see: Azadbakht et al. (2011 ).

Experimental

Crystal data

C₃₃H₃₀N₄O₄·H₂O
M_r = 564.63
Monoclinic, P 2₁ /c
a = 13.8808 (6) Å
b = 14.8951 (8) Å
c = 14.7517 (8) Å
β = 111.754 (2)°
V = 2832.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.5 × 0.3 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.671, T_max = 0.745
27583 measured reflections
5261 independent reflections
3757 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.195
S = 1.04
5261 reflections
395 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.79 (3)	1.99 (3)	2.596 (3)	133 (3)
N3—H3⋯O1	0.84 (3)	1.88 (3)	2.567 (3)	138 (3)
O5—H5D⋯O1ⁱ	0.95 (4)	1.82 (4)	2.747 (3)	164 (5)
N2—H2⋯O4ⁱⁱ	0.79 (3)	2.60 (3)	3.183 (4)	131 (2)
O5—H5C⋯O2ⁱⁱⁱ	0.94 (3)	1.91 (3)	2.839 (3)	170 (3)
C1—H1A⋯O5^iv	0.97	2.53	3.409 (4)	151
C2—H2A⋯O5^iv	0.97	2.55	3.359 (4)	140
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y, -z+1; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047465/qm2040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047465/qm2040Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047465/qm2040Isup3.cml

checkCIF report

Comment top

Schiff bases (imines) are known to be good ligands for metal ions. A number of the Schiff bases have antitumor properties, antioxidative activities, attractive electronic and photophysical properties. In addition, Schiff base derivatives incorporating a fluorescent moiety are appealing tools for optical sensing of metal ions (Azadbakht et al. 2011). The title compound, (I), crystallizes in the Monoclinic space group P2(1)/c. Figure 1 shows the ORTEP representation of the molecule with thermal ellipsoids at the 30% probability level. In the compound, there are π-π interactions between the naphthalene moiety and the nitrobenzene moiety with the distance of 3.516 (3) Å. The structural features of I (The bond lengths) provides evidence for the existence of a naphthoxide anions and the protonated imino N atoms in the crystal structure of I that stabilize by intramolecular hydrogen bond between the naphtholate oxygen and the iminium nitrogen (O-···H—N+). This molecular conformation is determined by the formation of pairs of intramolecular N±–H···O– (1.888 (3) Å) hydrogen bonds. These interactions lead to the formation of six- membered rings (see scheme). Details of the hydrogen-bonding geometry are given in Table 1. Each of these hydrogen-bonded rings adopts a nearly planar conformation. In the six-membered rings, the maximum deviation from the mean planes is 0.029 Å for H (N±–H). The crystal packing in compound (1) is stabilized by O—H···O– interactions (Fig. 2 and Table 1).

Related literature top

For related structures, see: Keypour et al. (2008); Zeng et al. (1999); McKee et al. (2006). For Schiff base derivatives incorporating a fluorescent moiety as tools for optical sensing of metal ions, see: Azadbakht et al. (2011).

Experimental top

A solution of NaOH (3 mmol) in methanol (10 cm3) was added to a suspension of N1-(2-nitrobenzyl)-N1-(2-aminoethyl)ethane-1,2- diamine trihydrochloride (0.357 g, 1 mmol) in methanol (10 cm3). The mixture was stirred at room temperature for a few minutes then filtered, and the precipitate was washed well with methanol (10 cm3). The washings and the filtrate were combined and to this solution was added 2-hydroxy-1-naphthaldehyde (0.344 g, 2 mmol). After refluxing the solution for 8 h on cooling the product was recovered as a yellow powder, which was recrystallized from methanol.

Structure description top

For related structures, see: Keypour et al. (2008); Zeng et al. (1999); McKee et al. (2006). For Schiff base derivatives incorporating a fluorescent moiety as tools for optical sensing of metal ions, see: Azadbakht et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title molecule with numbering of the atoms. Non H-atoms represented as displacement ellipsoids are plotted at the 30% probability level, while H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. A stereoview of part of the crystal packing, showing the intermolecular hydrogen bonds. For clarity, H atoms have been omitted for clarity except hydrogen of water. Hydrogen bonds are denoted by dashed lines.

1-[((E)-{2-[(2-Nitrobenzyl)(2-{[(E)-(2-oxidonaphthalen-1- yl)methylidene]azaniumyl}ethyl)amino]ethyl}azaniumylidene)methyl]naphthalen-2- olate monohydrate top

Crystal data top

C₃₃H₃₀N₄O₄·H₂O	F(000) = 1192
M_r = 564.63	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7294 reflections
a = 13.8808 (6) Å	θ = 2.2–24.5°
b = 14.8951 (8) Å	µ = 0.09 mm⁻¹
c = 14.7517 (8) Å	T = 296 K
β = 111.754 (2)°	Irregular, yellow
V = 2832.8 (2) Å³	0.5 × 0.3 × 0.2 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5261 independent reflections
Radiation source: fine-focus sealed tube	3757 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.671, T_max = 0.745	k = −18→18
27583 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1034P)² + 1.1914P] where P = (F_o² + 2F_c²)/3
5261 reflections	(Δ/σ)_max < 0.001
395 parameters	Δρ_max = 0.53 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₃₃H₃₀N₄O₄·H₂O	V = 2832.8 (2) Å³
M_r = 564.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8808 (6) Å	µ = 0.09 mm⁻¹
b = 14.8951 (8) Å	T = 296 K
c = 14.7517 (8) Å	0.5 × 0.3 × 0.2 mm
β = 111.754 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5261 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3757 reflections with I > 2σ(I)
T_min = 0.671, T_max = 0.745	R_int = 0.027
27583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	2 restraints
wR(F²) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.53 e Å⁻³
5261 reflections	Δρ_min = −0.35 e Å⁻³
395 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N2	0.02034 (16)	−0.10330 (14)	0.67594 (18)	0.0489 (5)
O5	−0.0441 (2)	0.22187 (17)	1.08799 (17)	0.0868 (7)
N3	0.08388 (19)	0.08971 (16)	0.95583 (16)	0.0575 (6)
O1	0.15835 (17)	−0.07002 (12)	0.98645 (15)	0.0683 (5)
O2	0.08995 (15)	−0.12590 (13)	0.53670 (13)	0.0642 (5)
C7	0.11465 (19)	−0.12276 (15)	0.73426 (18)	0.0457 (5)
H7	0.1288	−0.1223	0.8010	0.055*
N1	0.04699 (15)	0.08040 (13)	0.75101 (14)	0.0480 (5)
C14	0.20514 (19)	0.04119 (15)	1.11073 (18)	0.0459 (6)
C23	0.26511 (17)	0.06422 (16)	1.21139 (18)	0.0465 (6)
C30	0.4997 (3)	−0.1957 (2)	0.9093 (3)	0.0802 (9)
H30	0.5664	−0.2060	0.9542	0.096*
C31	0.4165 (3)	−0.1976 (2)	0.9386 (2)	0.0766 (9)
H31	0.4273	−0.2098	1.0035	0.092*
C32	0.3183 (2)	−0.18192 (19)	0.8738 (2)	0.0615 (7)
H32	0.2632	−0.1837	0.8953	0.074*
C33	0.29846 (19)	−0.16309 (15)	0.77513 (18)	0.0488 (6)
C24	0.19620 (18)	−0.14433 (15)	0.70377 (17)	0.0456 (5)
C6	−0.05483 (19)	−0.06051 (18)	0.7097 (2)	0.0535 (6)
H6A	−0.0383	−0.0755	0.7778	0.064*
H6B	−0.1235	−0.0838	0.6726	0.064*
C5	−0.05569 (19)	0.04108 (18)	0.69884 (19)	0.0525 (6)
H5A	−0.0782	0.0563	0.6301	0.063*
H5B	−0.1051	0.0667	0.7240	0.063*
C2	0.0439 (2)	0.16542 (17)	0.80026 (19)	0.0580 (7)
H2A	−0.0060	0.2051	0.7543	0.070*
H2B	0.1114	0.1939	0.8202	0.070*
C3	0.0154 (2)	0.15386 (19)	0.8878 (2)	0.0622 (7)
H3A	0.0200	0.2113	0.9202	0.075*
H3B	−0.0557	0.1330	0.8674	0.075*
C4	0.1394 (2)	0.10508 (16)	1.04679 (18)	0.0497 (6)
H4	0.1357	0.1619	1.0715	0.060*
C18	0.32210 (19)	−0.00420 (18)	1.2758 (2)	0.0561 (7)
C19	0.3780 (2)	0.0174 (2)	1.3744 (2)	0.0753 (9)
H19	0.4146	−0.0277	1.4168	0.090*
C20	0.3802 (2)	0.1015 (2)	1.4094 (2)	0.0769 (9)
H20	0.4179	0.1138	1.4748	0.092*
C29	0.4839 (2)	−0.1787 (2)	0.8144 (3)	0.0717 (8)
H29	0.5403	−0.1774	0.7948	0.086*
C28	0.3837 (2)	−0.16316 (17)	0.7452 (2)	0.0554 (6)
C22	0.2694 (2)	0.15089 (17)	1.25023 (19)	0.0538 (6)
H22	0.2331	0.1971	1.2095	0.065*
C21	0.3257 (2)	0.1693 (2)	1.3470 (2)	0.0658 (7)
H21	0.3273	0.2274	1.3705	0.079*
C17	0.3211 (2)	−0.09229 (19)	1.2381 (2)	0.0659 (8)
H17	0.3584	−0.1371	1.2805	0.079*
C16	0.2690 (2)	−0.11355 (18)	1.1444 (2)	0.0644 (8)
H16	0.2722	−0.1720	1.1236	0.077*
C15	0.2082 (2)	−0.04778 (16)	1.0751 (2)	0.0528 (6)
C1	0.10302 (19)	0.09324 (18)	0.68424 (19)	0.0524 (6)
H1A	0.0845	0.1513	0.6529	0.063*
H1B	0.0804	0.0477	0.6337	0.063*
C8	0.21990 (19)	0.08819 (16)	0.7341 (2)	0.0512 (6)
C13	0.2687 (2)	0.06145 (19)	0.8299 (2)	0.0611 (7)
H13	0.2285	0.0470	0.8662	0.073*
C12	0.3750 (2)	0.0555 (2)	0.8734 (3)	0.0786 (9)
H12	0.4054	0.0371	0.9381	0.094*
C11	0.4369 (3)	0.0767 (3)	0.8215 (3)	0.0909 (11)
H11	0.5087	0.0717	0.8505	0.109*
C10	0.3916 (3)	0.1051 (3)	0.7276 (3)	0.0870 (11)
H10	0.4323	0.1216	0.6925	0.104*
C9	0.2849 (2)	0.10932 (19)	0.6845 (2)	0.0627 (7)
N4	0.2402 (3)	0.1395 (2)	0.5833 (2)	0.0826 (8)
O4	0.1694 (3)	0.1045 (3)	0.5282 (2)	0.1449 (15)
O3	0.2758 (3)	0.2062 (2)	0.5574 (3)	0.1365 (12)
C25	0.1803 (2)	−0.13542 (16)	0.60255 (19)	0.0515 (6)
C26	0.2703 (2)	−0.13597 (19)	0.5771 (2)	0.0632 (7)
H26	0.2623	−0.1281	0.5121	0.076*
C27	0.3654 (2)	−0.14743 (19)	0.6443 (2)	0.0641 (7)
H27	0.4219	−0.1451	0.6249	0.077*
H5C	−0.067 (3)	0.270 (2)	1.044 (3)	0.105 (13)*
H5D	−0.092 (3)	0.177 (3)	1.053 (3)	0.141 (17)*
H2	0.007 (2)	−0.1011 (18)	0.619 (2)	0.051 (8)*
H3	0.091 (2)	0.039 (2)	0.935 (2)	0.074 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0522 (13)	0.0490 (11)	0.0453 (13)	−0.0033 (9)	0.0177 (11)	−0.0029 (10)
O5	0.116 (2)	0.0707 (15)	0.0578 (13)	−0.0088 (14)	0.0138 (13)	0.0015 (11)
N3	0.0777 (16)	0.0483 (12)	0.0494 (13)	0.0107 (11)	0.0271 (12)	0.0032 (10)
O1	0.0960 (15)	0.0449 (10)	0.0657 (13)	0.0019 (9)	0.0321 (11)	−0.0041 (9)
O2	0.0672 (12)	0.0779 (13)	0.0439 (10)	0.0098 (10)	0.0163 (9)	−0.0046 (9)
C7	0.0559 (14)	0.0388 (12)	0.0433 (13)	−0.0043 (10)	0.0194 (11)	0.0003 (9)
N1	0.0486 (11)	0.0496 (11)	0.0466 (11)	0.0005 (9)	0.0185 (9)	0.0004 (9)
C14	0.0519 (13)	0.0388 (12)	0.0545 (14)	0.0009 (10)	0.0284 (12)	0.0061 (10)
C23	0.0407 (12)	0.0496 (13)	0.0552 (14)	−0.0022 (10)	0.0245 (11)	0.0057 (11)
C30	0.0637 (19)	0.087 (2)	0.074 (2)	0.0162 (16)	0.0072 (17)	−0.0016 (17)
C31	0.080 (2)	0.084 (2)	0.0556 (17)	0.0185 (17)	0.0130 (16)	0.0047 (15)
C32	0.0633 (17)	0.0674 (17)	0.0532 (16)	0.0104 (13)	0.0206 (13)	0.0040 (13)
C33	0.0572 (15)	0.0383 (12)	0.0517 (14)	0.0018 (10)	0.0210 (12)	−0.0032 (10)
C24	0.0530 (14)	0.0382 (12)	0.0470 (13)	0.0011 (10)	0.0203 (11)	−0.0026 (10)
C6	0.0445 (13)	0.0646 (15)	0.0563 (15)	−0.0067 (11)	0.0244 (12)	−0.0007 (12)
C5	0.0435 (13)	0.0660 (16)	0.0522 (14)	0.0095 (11)	0.0225 (11)	0.0074 (12)
C2	0.0747 (18)	0.0478 (14)	0.0509 (15)	0.0078 (12)	0.0226 (13)	0.0047 (11)
C3	0.0715 (18)	0.0619 (16)	0.0516 (15)	0.0152 (13)	0.0212 (13)	0.0034 (12)
C4	0.0602 (15)	0.0432 (13)	0.0508 (15)	0.0011 (11)	0.0266 (12)	−0.0006 (11)
C18	0.0402 (13)	0.0569 (15)	0.0690 (18)	0.0022 (11)	0.0176 (12)	0.0100 (13)
C19	0.0534 (16)	0.087 (2)	0.070 (2)	0.0121 (15)	0.0056 (14)	0.0173 (17)
C20	0.0633 (18)	0.092 (2)	0.0613 (19)	0.0007 (16)	0.0066 (15)	−0.0062 (17)
C29	0.0544 (16)	0.0715 (19)	0.090 (2)	0.0035 (14)	0.0273 (16)	−0.0062 (17)
C28	0.0564 (15)	0.0457 (13)	0.0652 (17)	−0.0014 (11)	0.0239 (13)	−0.0068 (12)
C22	0.0587 (15)	0.0512 (14)	0.0550 (16)	−0.0014 (11)	0.0250 (13)	0.0026 (11)
C21	0.0641 (17)	0.0697 (18)	0.0621 (18)	−0.0049 (14)	0.0217 (14)	−0.0087 (14)
C17	0.0505 (15)	0.0568 (16)	0.084 (2)	0.0100 (12)	0.0178 (15)	0.0193 (15)
C16	0.0628 (17)	0.0395 (13)	0.091 (2)	0.0042 (12)	0.0288 (16)	0.0040 (13)
C15	0.0587 (15)	0.0437 (13)	0.0616 (17)	−0.0016 (11)	0.0291 (13)	0.0023 (11)
C1	0.0516 (14)	0.0580 (14)	0.0502 (14)	−0.0030 (11)	0.0218 (12)	0.0050 (11)
C8	0.0508 (14)	0.0430 (13)	0.0623 (16)	−0.0042 (10)	0.0239 (12)	−0.0054 (11)
C13	0.0528 (15)	0.0600 (16)	0.0649 (18)	−0.0040 (12)	0.0155 (13)	−0.0007 (13)
C12	0.0623 (19)	0.0710 (19)	0.084 (2)	−0.0035 (15)	0.0057 (17)	−0.0065 (16)
C11	0.0498 (18)	0.095 (3)	0.119 (3)	−0.0051 (17)	0.021 (2)	−0.020 (2)
C10	0.0569 (19)	0.105 (3)	0.108 (3)	−0.0128 (18)	0.041 (2)	−0.020 (2)
C9	0.0611 (17)	0.0603 (16)	0.0742 (19)	−0.0082 (13)	0.0337 (15)	−0.0151 (14)
N4	0.090 (2)	0.101 (2)	0.0743 (19)	−0.0289 (17)	0.0517 (18)	−0.0176 (16)
O4	0.104 (2)	0.246 (4)	0.083 (2)	−0.050 (3)	0.0329 (17)	0.015 (2)
O3	0.184 (3)	0.129 (3)	0.128 (3)	−0.024 (2)	0.094 (2)	0.011 (2)
C25	0.0621 (16)	0.0450 (13)	0.0494 (14)	0.0034 (11)	0.0230 (13)	−0.0054 (11)
C26	0.0756 (19)	0.0688 (17)	0.0542 (16)	0.0034 (14)	0.0343 (15)	0.0019 (13)
C27	0.0651 (18)	0.0650 (17)	0.076 (2)	−0.0045 (13)	0.0421 (16)	−0.0051 (14)

Geometric parameters (Å, º) top

N2—C7	1.305 (3)	C3—H3B	0.9700
N2—C6	1.459 (3)	C4—H4	0.9300
N2—H2	0.79 (3)	C18—C19	1.409 (4)
O5—H5C	0.94 (3)	C18—C17	1.423 (4)
O5—H5D	0.95 (4)	C19—C20	1.351 (5)
N3—C4	1.296 (3)	C19—H19	0.9300
N3—C3	1.455 (3)	C20—C21	1.386 (4)
N3—H3	0.84 (3)	C20—H20	0.9300
O1—C15	1.276 (3)	C29—C28	1.407 (4)
O2—C25	1.278 (3)	C29—H29	0.9300
C7—C24	1.401 (3)	C28—C27	1.434 (4)
C7—H7	0.9300	C22—C21	1.377 (4)
N1—C5	1.468 (3)	C22—H22	0.9300
N1—C2	1.468 (3)	C21—H21	0.9300
N1—C1	1.476 (3)	C17—C16	1.339 (4)
C14—C4	1.410 (3)	C17—H17	0.9300
C14—C15	1.432 (3)	C16—C15	1.441 (4)
C14—C23	1.449 (4)	C16—H16	0.9300
C23—C22	1.405 (3)	C1—C8	1.515 (4)
C23—C18	1.418 (3)	C1—H1A	0.9700
C30—C29	1.358 (5)	C1—H1B	0.9700
C30—C31	1.376 (5)	C8—C13	1.381 (4)
C30—H30	0.9300	C8—C9	1.392 (4)
C31—C32	1.364 (4)	C13—C12	1.378 (4)
C31—H31	0.9300	C13—H13	0.9300
C32—C33	1.406 (4)	C12—C11	1.383 (5)
C32—H32	0.9300	C12—H12	0.9300
C33—C28	1.407 (4)	C11—C10	1.359 (5)
C33—C24	1.447 (3)	C11—H11	0.9300
C24—C25	1.432 (3)	C10—C9	1.379 (4)
C6—C5	1.521 (4)	C10—H10	0.9300
C6—H6A	0.9700	C9—N4	1.459 (4)
C6—H6B	0.9700	N4—O4	1.142 (4)
C5—H5A	0.9700	N4—O3	1.232 (4)
C5—H5B	0.9700	C25—C26	1.432 (4)
C2—C3	1.495 (4)	C26—C27	1.336 (4)
C2—H2A	0.9700	C26—H26	0.9300
C2—H2B	0.9700	C27—H27	0.9300
C3—H3A	0.9700

C7—N2—C6	122.8 (2)	C20—C19—C18	122.1 (3)
C7—N2—H2	119 (2)	C20—C19—H19	119.0
C6—N2—H2	116 (2)	C18—C19—H19	119.0
H5C—O5—H5D	100 (4)	C19—C20—C21	119.5 (3)
C4—N3—C3	125.7 (2)	C19—C20—H20	120.2
C4—N3—H3	116 (2)	C21—C20—H20	120.2
C3—N3—H3	119 (2)	C30—C29—C28	121.1 (3)
N2—C7—C24	124.9 (2)	C30—C29—H29	119.5
N2—C7—H7	117.6	C28—C29—H29	119.5
C24—C7—H7	117.6	C33—C28—C29	119.6 (3)
C5—N1—C2	113.8 (2)	C33—C28—C27	118.6 (2)
C5—N1—C1	110.56 (19)	C29—C28—C27	121.8 (3)
C2—N1—C1	109.7 (2)	C21—C22—C23	121.8 (3)
C4—C14—C15	118.6 (2)	C21—C22—H22	119.1
C4—C14—C23	120.6 (2)	C23—C22—H22	119.1
C15—C14—C23	120.7 (2)	C22—C21—C20	120.2 (3)
C22—C23—C18	117.3 (2)	C22—C21—H21	119.9
C22—C23—C14	123.8 (2)	C20—C21—H21	119.9
C18—C23—C14	118.9 (2)	C16—C17—C18	123.0 (2)
C29—C30—C31	119.6 (3)	C16—C17—H17	118.5
C29—C30—H30	120.2	C18—C17—H17	118.5
C31—C30—H30	120.2	C17—C16—C15	121.4 (3)
C32—C31—C30	120.9 (3)	C17—C16—H16	119.3
C32—C31—H31	119.5	C15—C16—H16	119.3
C30—C31—H31	119.5	O1—C15—C14	122.5 (2)
C31—C32—C33	121.4 (3)	O1—C15—C16	120.2 (2)
C31—C32—H32	119.3	C14—C15—C16	117.3 (2)
C33—C32—H32	119.3	N1—C1—C8	113.9 (2)
C32—C33—C28	117.4 (2)	N1—C1—H1A	108.8
C32—C33—C24	123.7 (2)	C8—C1—H1A	108.8
C28—C33—C24	119.0 (2)	N1—C1—H1B	108.8
C7—C24—C25	118.8 (2)	C8—C1—H1B	108.8
C7—C24—C33	120.1 (2)	H1A—C1—H1B	107.7
C25—C24—C33	120.5 (2)	C13—C8—C9	115.8 (3)
N2—C6—C5	112.2 (2)	C13—C8—C1	122.8 (2)
N2—C6—H6A	109.2	C9—C8—C1	121.4 (2)
C5—C6—H6A	109.2	C12—C13—C8	122.0 (3)
N2—C6—H6B	109.2	C12—C13—H13	119.0
C5—C6—H6B	109.2	C8—C13—H13	119.0
H6A—C6—H6B	107.9	C13—C12—C11	120.4 (3)
N1—C5—C6	111.9 (2)	C13—C12—H12	119.8
N1—C5—H5A	109.2	C11—C12—H12	119.8
C6—C5—H5A	109.2	C10—C11—C12	119.2 (3)
N1—C5—H5B	109.2	C10—C11—H11	120.4
C6—C5—H5B	109.2	C12—C11—H11	120.4
H5A—C5—H5B	107.9	C11—C10—C9	119.8 (3)
N1—C2—C3	113.2 (2)	C11—C10—H10	120.1
N1—C2—H2A	108.9	C9—C10—H10	120.1
C3—C2—H2A	108.9	C10—C9—C8	122.8 (3)
N1—C2—H2B	108.9	C10—C9—N4	117.6 (3)
C3—C2—H2B	108.9	C8—C9—N4	119.6 (3)
H2A—C2—H2B	107.8	O4—N4—O3	119.1 (4)
N3—C3—C2	110.9 (2)	O4—N4—C9	121.0 (3)
N3—C3—H3A	109.5	O3—N4—C9	119.8 (3)
C2—C3—H3A	109.5	O2—C25—C26	120.5 (2)
N3—C3—H3B	109.5	O2—C25—C24	122.1 (2)
C2—C3—H3B	109.5	C26—C25—C24	117.4 (2)
H3A—C3—H3B	108.0	C27—C26—C25	121.6 (3)
N3—C4—C14	124.2 (2)	C27—C26—H26	119.2
N3—C4—H4	117.9	C25—C26—H26	119.2
C14—C4—H4	117.9	C26—C27—C28	122.5 (3)
C19—C18—C23	119.0 (3)	C26—C27—H27	118.7
C19—C18—C17	122.4 (3)	C28—C27—H27	118.7
C23—C18—C17	118.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.79 (3)	1.99 (3)	2.596 (3)	133 (3)
N3—H3···O1	0.84 (3)	1.88 (3)	2.567 (3)	138 (3)
N3—H3···N1	0.84 (3)	2.62 (3)	2.875 (3)	99 (2)
O5—H5D···O1ⁱ	0.95 (4)	1.82 (4)	2.747 (3)	164 (5)
N2—H2···O4ⁱⁱ	0.79 (3)	2.60 (3)	3.183 (4)	131 (2)
O5—H5C···O2ⁱⁱⁱ	0.94 (3)	1.91 (3)	2.839 (3)	170 (3)
C1—H1A···O5^iv	0.97	2.53	3.409 (4)	151
C2—H2A···O5^iv	0.97	2.55	3.359 (4)	140

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

Experimental details

Crystal data
Chemical formula	C₃₃H₃₀N₄O₄·H₂O
M_r	564.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.8808 (6), 14.8951 (8), 14.7517 (8)
β (°)	111.754 (2)
V (Å³)	2832.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.5 × 0.3 × 0.2

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.671, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	27583, 5261, 3757
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.195, 1.04
No. of reflections	5261
No. of parameters	395
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.79 (3)	1.99 (3)	2.596 (3)	133 (3)
N3—H3···O1	0.84 (3)	1.88 (3)	2.567 (3)	138 (3)
N3—H3···N1	0.84 (3)	2.62 (3)	2.875 (3)	99 (2)
O5—H5D···O1ⁱ	0.95 (4)	1.82 (4)	2.747 (3)	164 (5)
N2—H2···O4ⁱⁱ	0.79 (3)	2.60 (3)	3.183 (4)	131 (2)
O5—H5C···O2ⁱⁱⁱ	0.94 (3)	1.91 (3)	2.839 (3)	170 (3)
C1—H1A···O5^iv	0.97	2.53	3.409 (4)	151
C2—H2A···O5^iv	0.97	2.55	3.359 (4)	140

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

Acknowledgements

We are grateful to the Islamic Azad University of Khorramabad for financial support.

References

Azadbakht, R., Parviz, M., Tamari, E., Keypour, H. & Golbedaghi, R. (2011). Spectrochim. Acta A, pp. 200–204. CrossRef Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Keypour, H., Azadbakht, R., Salehzadeh, S., Khanmohammadi, H., Khavasi, H. & Adams, H. (2008). J. Organomet. Chem. 693, 2237–2243. Web of Science CSD CrossRef CAS Google Scholar
McKee, V., Morgan, G. G. & Nelson, J. (2006). Acta Cryst. E62, o3747–o3749. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, Q., Qian, M., Gou, S., Fun, H. K., Duan, C. & You, X. (1999). Inorg. Chim. Acta, 294, 1–7. Web of Science CSD CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[((E)-{2-[(2-Nitro­benz­yl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methyl­­idene]aza­nium­yl}eth­yl)amino]­eth­yl}aza­niumyl­­idene)meth­yl]naphthalen-2-olate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[((E)-{2-[(2-Nitrobenzyl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methylidene]azaniumyl}ethyl)amino]ethyl}azaniumylidene)methyl]naphthalen-2-olate monohydrate