5,5′-Dimeth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol

Kargar, H.; Kia, R.; Khan, I.U.; Sahraei, A.; Aberoomand Azar, P.

doi:10.1107/S1600536810007282

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o728

doi:10.1107/S1600536810007282

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5,5′-Dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol

Hadi Kargar,^a Reza Kia,^b ‡ Islam Ullah Khan,^c ^* Atefeh Sahraei ^a and Parviz Aberoomand Azar ^b

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 20 February 2010; accepted 25 February 2010; online 3 March 2010)

In the crystal structure of the title compound, C₂₄H₂₄N₂O₄, the dihedral angles between the central and the two outer benzene rings are 48.12 (8) and 21.44 (8)°. Intramolecular O—H⋯N hydrogen bonding generates S(6) rings.

Related literature

For graph-set notation see: Bernstein et al. (1995 ). For a related structure see: Kargar et al. (2010 ).

Experimental

Crystal data

C₂₄H₂₄N₂O₄
M_r = 404.45
Monoclinic, P 2₁ /n
a = 6.6720 (3) Å
b = 14.3192 (6) Å
c = 21.7396 (9) Å
β = 95.177 (2)°
V = 2068.48 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.42 × 0.32 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.964, T_max = 0.984
23605 measured reflections
5123 independent reflections
3112 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.01
5123 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.95	1.78	2.6158 (18)	145
O2—H2⋯N2	0.96	1.71	2.5791 (17)	150

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007282/nc2177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007282/nc2177Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound was determined to clarify the identity of the synthetic product and to compare the structural changes upon complexation with Cu(II) and Ni(II) ions in future works.

In the crystal structure of the title compound the dihedral angles between the central benzene ring and the two outer benzene rings amount to 48.12 (8) and 21.44 (8)°. The bond lengths and angles are comparable to those in a related structure reported recently (Kargar et al., 2010). Intramolecular O—H···N hydrogen bonding is found that generates six-membered S(6) rings. (Bernstein et al., 1995) (Table 1).

Related literature top

For graph-set notation see: Bernstein et al. (1995). For a related structure see: Kargar et al. (2010).

Experimental top

The title compound was synthesized by adding 4-methoxy-salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-o-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Crystal structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are drawn as dashed lines.

5,5'-Dimethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₄H₂₄N₂O₄	F(000) = 856
M_r = 404.45	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5431 reflections
a = 6.6720 (3) Å	θ = 2.4–26.4°
b = 14.3192 (6) Å	µ = 0.09 mm⁻¹
c = 21.7396 (9) Å	T = 296 K
β = 95.177 (2)°	Block, yellow
V = 2068.48 (15) Å³	0.42 × 0.32 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5123 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→6
T_min = 0.964, T_max = 0.984	k = −19→13
23605 measured reflections	l = −28→28

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0473P)² + 0.4824P] where P = (F_o² + 2F_c²)/3
5123 reflections	(Δ/σ)_max = 0.001
274 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₄H₂₄N₂O₄	V = 2068.48 (15) Å³
M_r = 404.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6720 (3) Å	µ = 0.09 mm⁻¹
b = 14.3192 (6) Å	T = 296 K
c = 21.7396 (9) Å	0.42 × 0.32 × 0.18 mm
β = 95.177 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5123 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3112 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.984	R_int = 0.034
23605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
5123 reflections	Δρ_min = −0.16 e Å⁻³
274 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 > 2sigma(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
O1	0.80563 (17)	1.05843 (9)	0.32895 (6)	0.0605 (4)
H1	0.8156	1.0315	0.2894	0.091*
O2	0.61776 (18)	0.82964 (9)	0.31447 (5)	0.0601 (4)
H2	0.6865	0.8448	0.2791	0.090*
O3	1.2169 (2)	1.11971 (10)	0.51656 (6)	0.0720 (4)
O4	0.03885 (19)	0.66990 (9)	0.35951 (6)	0.0634 (4)
N1	0.9786 (2)	0.97538 (9)	0.24052 (6)	0.0424 (3)
N2	0.6943 (2)	0.84762 (9)	0.20089 (6)	0.0437 (3)
C1	0.9858 (2)	1.05519 (11)	0.36245 (7)	0.0423 (4)
C2	1.0013 (3)	1.09115 (12)	0.42227 (8)	0.0500 (4)
H2A	0.8890	1.1163	0.4386	0.060*
C3	1.1851 (3)	1.08903 (12)	0.45710 (8)	0.0517 (4)
C4	1.3543 (3)	1.05316 (14)	0.43257 (8)	0.0579 (5)
H4A	1.4783	1.0535	0.4558	0.070*
C5	1.3372 (3)	1.01751 (13)	0.37431 (8)	0.0516 (4)
H5A	1.4507	0.9926	0.3585	0.062*
C6	1.1544 (2)	1.01719 (11)	0.33750 (7)	0.0406 (4)
C7	1.1429 (2)	0.98008 (11)	0.27563 (7)	0.0423 (4)
H7A	1.2605	0.9585	0.2605	0.051*
C8	0.9810 (2)	0.93897 (11)	0.18012 (7)	0.0405 (4)
C9	1.1249 (2)	0.96510 (12)	0.14096 (7)	0.0469 (4)
H9A	1.2213	1.0091	0.1546	0.056*
C10	1.1297 (3)	0.92783 (13)	0.08221 (7)	0.0500 (4)
C11	0.9840 (3)	0.86310 (13)	0.06121 (8)	0.0513 (4)
C12	0.8381 (3)	0.83831 (12)	0.09976 (8)	0.0499 (4)
H12A	0.7403	0.7952	0.0856	0.060*
C13	0.8323 (2)	0.87538 (11)	0.15879 (7)	0.0411 (4)
C14	0.5294 (2)	0.80505 (11)	0.18428 (7)	0.0437 (4)
H14A	0.4933	0.7952	0.1425	0.052*
C15	0.3988 (2)	0.77214 (11)	0.22869 (7)	0.0396 (4)
C16	0.2190 (2)	0.72666 (12)	0.20999 (8)	0.0468 (4)
H16A	0.1827	0.7193	0.1680	0.056*
C17	0.0929 (3)	0.69218 (12)	0.25145 (8)	0.0498 (4)
H17A	−0.0263	0.6620	0.2377	0.060*
C18	0.1477 (3)	0.70345 (11)	0.31392 (8)	0.0468 (4)
C19	0.3228 (3)	0.75016 (12)	0.33444 (8)	0.0491 (4)
H19A	0.3560	0.7585	0.3766	0.059*
C20	0.4481 (2)	0.78427 (11)	0.29270 (7)	0.0430 (4)
C21	1.0541 (4)	1.15847 (16)	0.54511 (10)	0.0783 (7)
H21A	1.0992	1.1773	0.5864	0.117*
H21B	0.9495	1.1127	0.5463	0.117*
H21C	1.0031	1.2118	0.5220	0.117*
C22	−0.1404 (3)	0.61818 (16)	0.34162 (11)	0.0744 (6)
H22A	−0.2026	0.5996	0.3778	0.112*
H22B	−0.1069	0.5637	0.3189	0.112*
H22C	−0.2319	0.6565	0.3161	0.112*
C23	1.2948 (3)	0.95713 (16)	0.04274 (9)	0.0708 (6)
H23A	1.2358	0.9807	0.0039	0.106*
H23B	1.3781	0.9042	0.0356	0.106*
H23C	1.3753	1.0050	0.0637	0.106*
C24	0.9800 (3)	0.81878 (17)	−0.00213 (9)	0.0763 (6)
H24A	0.8676	0.7769	−0.0081	0.114*
H24B	1.1026	0.7847	−0.0053	0.114*
H24C	0.9673	0.8666	−0.0332	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0412 (7)	0.0832 (9)	0.0572 (8)	0.0083 (6)	0.0045 (6)	−0.0120 (6)
O2	0.0573 (8)	0.0784 (9)	0.0436 (7)	−0.0228 (7)	−0.0005 (6)	−0.0057 (6)
O3	0.0826 (10)	0.0852 (10)	0.0475 (7)	−0.0034 (8)	0.0031 (7)	−0.0143 (7)
O4	0.0621 (8)	0.0663 (8)	0.0646 (8)	−0.0111 (7)	0.0203 (7)	0.0011 (6)
N1	0.0423 (8)	0.0461 (8)	0.0390 (7)	−0.0018 (6)	0.0049 (6)	−0.0045 (6)
N2	0.0458 (8)	0.0452 (8)	0.0405 (7)	−0.0030 (6)	0.0063 (6)	−0.0035 (6)
C1	0.0393 (9)	0.0436 (9)	0.0439 (9)	−0.0004 (7)	0.0037 (7)	0.0004 (7)
C2	0.0556 (11)	0.0462 (9)	0.0501 (10)	0.0032 (8)	0.0155 (8)	−0.0041 (8)
C3	0.0633 (12)	0.0514 (10)	0.0398 (9)	−0.0063 (9)	0.0019 (8)	−0.0017 (8)
C4	0.0498 (11)	0.0734 (13)	0.0491 (10)	−0.0007 (9)	−0.0045 (8)	0.0008 (9)
C5	0.0442 (10)	0.0628 (11)	0.0480 (10)	0.0038 (8)	0.0046 (8)	0.0017 (8)
C6	0.0402 (9)	0.0414 (8)	0.0402 (8)	−0.0005 (7)	0.0049 (7)	0.0012 (7)
C7	0.0444 (10)	0.0406 (8)	0.0430 (9)	0.0029 (7)	0.0099 (7)	0.0004 (7)
C8	0.0436 (9)	0.0404 (8)	0.0377 (8)	0.0042 (7)	0.0053 (7)	−0.0011 (7)
C9	0.0463 (10)	0.0485 (10)	0.0463 (9)	−0.0020 (8)	0.0059 (7)	0.0018 (7)
C10	0.0526 (11)	0.0570 (11)	0.0417 (9)	0.0081 (8)	0.0122 (8)	0.0058 (8)
C11	0.0570 (11)	0.0579 (11)	0.0398 (9)	0.0073 (9)	0.0076 (8)	−0.0031 (8)
C12	0.0525 (11)	0.0515 (10)	0.0456 (10)	−0.0012 (8)	0.0044 (8)	−0.0080 (8)
C13	0.0436 (9)	0.0419 (8)	0.0381 (8)	0.0035 (7)	0.0055 (7)	−0.0005 (7)
C14	0.0485 (10)	0.0447 (9)	0.0374 (8)	0.0026 (8)	0.0016 (7)	−0.0030 (7)
C15	0.0411 (9)	0.0371 (8)	0.0402 (8)	0.0034 (7)	0.0003 (7)	−0.0027 (6)
C16	0.0473 (10)	0.0490 (9)	0.0431 (9)	0.0009 (8)	−0.0026 (8)	−0.0052 (7)
C17	0.0414 (10)	0.0482 (10)	0.0590 (11)	−0.0040 (8)	0.0007 (8)	−0.0057 (8)
C18	0.0480 (10)	0.0397 (9)	0.0541 (10)	0.0028 (7)	0.0120 (8)	0.0009 (7)
C19	0.0559 (11)	0.0537 (10)	0.0375 (9)	−0.0031 (8)	0.0017 (8)	−0.0001 (7)
C20	0.0429 (9)	0.0421 (9)	0.0432 (9)	−0.0017 (7)	−0.0009 (7)	−0.0033 (7)
C21	0.1081 (18)	0.0731 (14)	0.0560 (12)	0.0039 (13)	0.0201 (12)	−0.0142 (10)
C22	0.0542 (12)	0.0735 (14)	0.0982 (17)	−0.0124 (10)	0.0209 (11)	0.0092 (12)
C23	0.0717 (14)	0.0888 (15)	0.0553 (11)	−0.0013 (12)	0.0244 (10)	0.0064 (10)
C24	0.0886 (16)	0.0914 (16)	0.0512 (11)	0.0007 (13)	0.0195 (11)	−0.0204 (11)

Geometric parameters (Å, º) top

O1—C1	1.3489 (19)	C10—C23	1.515 (2)
O1—H1	0.9496	C11—C12	1.387 (2)
O2—C20	1.3532 (19)	C11—C24	1.514 (2)
O2—H2	0.9553	C12—C13	1.392 (2)
O3—C3	1.364 (2)	C12—H12A	0.9300
O3—C21	1.412 (2)	C14—C15	1.437 (2)
O4—C18	1.3678 (19)	C14—H14A	0.9300
O4—C22	1.430 (2)	C15—C16	1.393 (2)
N1—C7	1.2798 (19)	C15—C20	1.411 (2)
N1—C8	1.4142 (19)	C16—C17	1.379 (2)
N2—C14	1.281 (2)	C16—H16A	0.9300
N2—C13	1.412 (2)	C17—C18	1.384 (2)
C1—C2	1.394 (2)	C17—H17A	0.9300
C1—C6	1.402 (2)	C18—C19	1.385 (2)
C2—C3	1.383 (2)	C19—C20	1.377 (2)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.389 (3)	C21—H21A	0.9600
C4—C5	1.361 (2)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.397 (2)	C22—H22A	0.9600
C5—H5A	0.9300	C22—H22B	0.9600
C6—C7	1.442 (2)	C22—H22C	0.9600
C7—H7A	0.9300	C23—H23A	0.9600
C8—C9	1.391 (2)	C23—H23B	0.9600
C8—C13	1.395 (2)	C23—H23C	0.9600
C9—C10	1.387 (2)	C24—H24A	0.9600
C9—H9A	0.9300	C24—H24B	0.9600
C10—C11	1.390 (2)	C24—H24C	0.9600

C1—O1—H1	110.0	N2—C14—C15	121.61 (15)
C20—O2—H2	106.0	N2—C14—H14A	119.2
C3—O3—C21	118.90 (16)	C15—C14—H14A	119.2
C18—O4—C22	118.07 (15)	C16—C15—C20	117.59 (15)
C7—N1—C8	119.49 (13)	C16—C15—C14	121.04 (15)
C14—N2—C13	123.01 (14)	C20—C15—C14	121.37 (15)
O1—C1—C2	118.58 (14)	C17—C16—C15	122.47 (16)
O1—C1—C6	120.76 (14)	C17—C16—H16A	118.8
C2—C1—C6	120.65 (15)	C15—C16—H16A	118.8
C3—C2—C1	119.35 (16)	C16—C17—C18	118.49 (16)
C3—C2—H2A	120.3	C16—C17—H17A	120.8
C1—C2—H2A	120.3	C18—C17—H17A	120.8
O3—C3—C2	124.51 (17)	O4—C18—C17	124.02 (16)
O3—C3—C4	114.88 (17)	O4—C18—C19	115.09 (15)
C2—C3—C4	120.61 (16)	C17—C18—C19	120.88 (15)
C5—C4—C3	119.56 (17)	C20—C19—C18	120.23 (15)
C5—C4—H4A	120.2	C20—C19—H19A	119.9
C3—C4—H4A	120.2	C18—C19—H19A	119.9
C4—C5—C6	121.98 (16)	O2—C20—C19	118.56 (15)
C4—C5—H5A	119.0	O2—C20—C15	121.14 (14)
C6—C5—H5A	119.0	C19—C20—C15	120.31 (15)
C5—C6—C1	117.82 (14)	O3—C21—H21A	109.5
C5—C6—C7	120.37 (15)	O3—C21—H21B	109.5
C1—C6—C7	121.80 (14)	H21A—C21—H21B	109.5
N1—C7—C6	123.11 (14)	O3—C21—H21C	109.5
N1—C7—H7A	118.4	H21A—C21—H21C	109.5
C6—C7—H7A	118.4	H21B—C21—H21C	109.5
C9—C8—C13	118.80 (14)	O4—C22—H22A	109.5
C9—C8—N1	122.38 (15)	O4—C22—H22B	109.5
C13—C8—N1	118.81 (13)	H22A—C22—H22B	109.5
C10—C9—C8	122.33 (16)	O4—C22—H22C	109.5
C10—C9—H9A	118.8	H22A—C22—H22C	109.5
C8—C9—H9A	118.8	H22B—C22—H22C	109.5
C9—C10—C11	119.02 (15)	C10—C23—H23A	109.5
C9—C10—C23	119.55 (17)	C10—C23—H23B	109.5
C11—C10—C23	121.43 (16)	H23A—C23—H23B	109.5
C12—C11—C10	118.72 (15)	C10—C23—H23C	109.5
C12—C11—C24	119.12 (17)	H23A—C23—H23C	109.5
C10—C11—C24	122.16 (16)	H23B—C23—H23C	109.5
C11—C12—C13	122.60 (16)	C11—C24—H24A	109.5
C11—C12—H12A	118.7	C11—C24—H24B	109.5
C13—C12—H12A	118.7	H24A—C24—H24B	109.5
C12—C13—C8	118.50 (14)	C11—C24—H24C	109.5
C12—C13—N2	124.33 (15)	H24A—C24—H24C	109.5
C8—C13—N2	116.99 (13)	H24B—C24—H24C	109.5

O1—C1—C2—C3	−179.53 (15)	C10—C11—C12—C13	−0.3 (3)
C6—C1—C2—C3	−0.1 (2)	C24—C11—C12—C13	179.54 (17)
C21—O3—C3—C2	−1.4 (3)	C11—C12—C13—C8	−0.9 (3)
C21—O3—C3—C4	179.18 (18)	C11—C12—C13—N2	−175.78 (16)
C1—C2—C3—O3	−178.09 (16)	C9—C8—C13—C12	2.1 (2)
C1—C2—C3—C4	1.3 (3)	N1—C8—C13—C12	−178.65 (15)
O3—C3—C4—C5	177.60 (17)	C9—C8—C13—N2	177.33 (14)
C2—C3—C4—C5	−1.8 (3)	N1—C8—C13—N2	−3.4 (2)
C3—C4—C5—C6	1.2 (3)	C14—N2—C13—C12	−19.3 (2)
C4—C5—C6—C1	0.0 (3)	C14—N2—C13—C8	165.74 (15)
C4—C5—C6—C7	179.05 (17)	C13—N2—C14—C15	175.71 (14)
O1—C1—C6—C5	178.89 (15)	N2—C14—C15—C16	179.45 (15)
C2—C1—C6—C5	−0.6 (2)	N2—C14—C15—C20	−0.8 (2)
O1—C1—C6—C7	−0.1 (2)	C20—C15—C16—C17	−1.4 (2)
C2—C1—C6—C7	−179.59 (15)	C14—C15—C16—C17	178.33 (15)
C8—N1—C7—C6	179.24 (14)	C15—C16—C17—C18	0.0 (3)
C5—C6—C7—N1	177.82 (15)	C22—O4—C18—C17	1.5 (2)
C1—C6—C7—N1	−3.2 (2)	C22—O4—C18—C19	−177.94 (16)
C7—N1—C8—C9	−45.6 (2)	C16—C17—C18—O4	−177.89 (15)
C7—N1—C8—C13	135.15 (16)	C16—C17—C18—C19	1.5 (3)
C13—C8—C9—C10	−2.2 (2)	O4—C18—C19—C20	177.83 (15)
N1—C8—C9—C10	178.57 (15)	C17—C18—C19—C20	−1.6 (3)
C8—C9—C10—C11	1.0 (3)	C18—C19—C20—O2	179.93 (15)
C8—C9—C10—C23	−178.04 (16)	C18—C19—C20—C15	0.2 (2)
C9—C10—C11—C12	0.2 (3)	C16—C15—C20—O2	−178.47 (14)
C23—C10—C11—C12	179.28 (17)	C14—C15—C20—O2	1.8 (2)
C9—C10—C11—C24	−179.56 (18)	C16—C15—C20—C19	1.3 (2)
C23—C10—C11—C24	−0.5 (3)	C14—C15—C20—C19	−178.46 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95	1.78	2.6158 (18)	145
O2—H2···N2	0.96	1.71	2.5791 (17)	150

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₄
M_r	404.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	6.6720 (3), 14.3192 (6), 21.7396 (9)
β (°)	95.177 (2)
V (Å³)	2068.48 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.42 × 0.32 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.964, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	23605, 5123, 3112
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.01
No. of reflections	5123
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.9500	1.7800	2.6158 (18)	145.00
O2—H2···N2	0.9600	1.7100	2.5791 (17)	150.00

Footnotes

‡Thomson Reuters Researcher ID: A-5471-2009. Additional corresponding author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HK and AS thank PNU for financial support. IUK thanks GC University of Lahore, Pakistan, for the research facilities. RK and PAA thank the Science & Research Branch, Islamic Azad University.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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