2,3-Dimeth­oxy­benzaldehyde azine

Ali, Q.; Anis, I.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536811003217

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o531

doi:10.1107/S1600536811003217

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2,3-Dimethoxybenzaldehyde azine

Qamar Ali,^a Itrat Anis,^a M. Raza Shah ^a and Seik Weng Ng ^b ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 7527, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 January 2011; accepted 25 January 2011; online 29 January 2011)

There are one-and-a-half independent molecules in the asymmetric unit of the title compound, C₁₈H₂₀N₂O₄. One molecule is centrosymmetric with the mid-point of the N—N bond located on a center of inversion. In the other, which lies on a general position, the benzene rings are aligned at 21.6 (1)°. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal strcture.

Related literature

For the structure of 2,4-dibenzaldehyde azine, see: Islam et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₄
M_r = 328.36
Monoclinic, P 2₁ /n
a = 8.0294 (2) Å
b = 17.9415 (5) Å
c = 17.5258 (4) Å
β = 96.660 (2)°
V = 2507.72 (11) Å³
Z = 6
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.770, T_max = 1.000
12722 measured reflections
5600 independent reflections
4465 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.03
5600 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O3ⁱ	0.98	2.45	3.288 (2)	143
C14—H14A⋯O5ⁱⁱ	0.95	2.37	3.2890 (19)	161
C18—H18C⋯O6ⁱⁱ	0.98	2.54	3.5229 (19)	178
C27—H27C⋯O2ⁱⁱⁱ	0.98	2.52	3.2656 (19)	133
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-2, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003217/xu5148sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003217/xu5148Isup2.hkl

checkCIF report

Comment top

Several methoxy-substituted benzaldehyde azines have been reported, e.g., 2,4-dimethyoxybenzaldehyde azine (Islam et al., 2009). The compounds feature a C═N–N═C linkage that allows the two aromatic sytems to interaction. Such interaction results in a deep yellow coloration. In the reported compound, the rings are nearly co-planar. In the 2,3-dimethoxy analog (Scheme I), the rings are co-planar in the indpendent molecule lying on a center-of-inversion; in the other molecule, the rings are severely twisted (Fig. 1). Intermolecular weak C—H···O hydrogen bonding is present in the crystal strcture (Table 1).

Related literature top

For the structure of 2,4-dibenzaldehyde azine, see: Islam et al. (2009).

Experimental top

2,3-Dimethyoxybenzaldehyde (1 g, 6 mmol) was dissolved in ethanol (15 ml) and to the solution was added hydrazine hydrate (0.3 ml, 6 mmol) followed by 5 drops of acetic acid. The mixture was heated for 3 h; slow evaporation of the solvent gave yellow crystals in 80% yield.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two molecules of C₁₈H₂₀N₂O₄ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2,3-Dimethoxybenzaldehyde azine top

Crystal data top

C₁₈H₂₀N₂O₄	F(000) = 1044
M_r = 328.36	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5647 reflections
a = 8.0294 (2) Å	θ = 2.3–29.3°
b = 17.9415 (5) Å	µ = 0.09 mm⁻¹
c = 17.5258 (4) Å	T = 100 K
β = 96.660 (2)°	Prism, yellow
V = 2507.72 (11) Å³	0.30 × 0.25 × 0.20 mm
Z = 6

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5600 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4465 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→22
T_min = 0.770, T_max = 1.000	l = −15→22
12722 measured reflections

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 = 1.03	w = 1/[σ²(F_o²) + (0.0541P)² + 1.0146P] where P = (F_o² + 2F_c²)/3
5600 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₄	V = 2507.72 (11) Å³
M_r = 328.36	Z = 6
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0294 (2) Å	µ = 0.09 mm⁻¹
b = 17.9415 (5) Å	T = 100 K
c = 17.5258 (4) Å	0.30 × 0.25 × 0.20 mm
β = 96.660 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5600 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4465 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.029
12722 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
5600 reflections	Δρ_min = −0.22 e Å⁻³
325 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.44670 (14)	0.12618 (6)	0.46827 (6)	0.0233 (3)
O2	1.51150 (15)	0.22434 (7)	0.36049 (6)	0.0274 (3)
O3	0.80577 (13)	0.08624 (6)	0.73656 (6)	0.0206 (2)
O4	0.88407 (14)	−0.04039 (6)	0.81165 (6)	0.0229 (3)
O5	−0.14383 (13)	0.28732 (6)	0.56994 (6)	0.0207 (3)
O6	−0.24191 (14)	0.39718 (7)	0.47148 (6)	0.0270 (3)
N1	0.99742 (18)	0.02682 (8)	0.47015 (7)	0.0244 (3)
N2	0.33013 (17)	0.14903 (8)	0.66135 (7)	0.0230 (3)
N3	0.32823 (17)	0.21485 (8)	0.61681 (7)	0.0219 (3)
C1	1.1291 (2)	0.06789 (9)	0.47776 (9)	0.0227 (3)
H1	1.2113	0.0607	0.5207	0.027*
C2	1.1546 (2)	0.12573 (9)	0.42122 (9)	0.0216 (3)
C3	1.3166 (2)	0.15129 (9)	0.41631 (8)	0.0210 (3)
C4	1.3473 (2)	0.20464 (9)	0.36085 (9)	0.0225 (3)
C5	1.2143 (2)	0.23323 (10)	0.31222 (9)	0.0270 (4)
H5	1.2338	0.2696	0.2749	0.032*
C6	1.0521 (2)	0.20851 (10)	0.31822 (10)	0.0284 (4)
H6	0.9613	0.2289	0.2852	0.034*
C7	1.0209 (2)	0.15493 (10)	0.37118 (9)	0.0263 (4)
H7	0.9097	0.1379	0.3738	0.032*
C8	1.5554 (2)	0.07435 (10)	0.43631 (10)	0.0290 (4)
H8A	1.6445	0.0589	0.4761	0.044*
H8B	1.6052	0.0982	0.3940	0.044*
H8C	1.4907	0.0306	0.4169	0.044*
C9	1.5503 (2)	0.27571 (11)	0.30281 (11)	0.0336 (4)
H9A	1.6713	0.2852	0.3087	0.050*
H9B	1.4902	0.3226	0.3083	0.050*
H9C	1.5161	0.2545	0.2519	0.050*
C10	0.4791 (2)	0.12549 (9)	0.68026 (8)	0.0200 (3)
H10A	0.5707	0.1537	0.6659	0.024*
C11	0.51268 (19)	0.05616 (9)	0.72347 (8)	0.0195 (3)
C12	0.67881 (19)	0.03737 (9)	0.74863 (8)	0.0186 (3)
C13	0.71782 (19)	−0.02919 (9)	0.78884 (8)	0.0194 (3)
C14	0.5896 (2)	−0.07717 (9)	0.80322 (9)	0.0218 (3)
H14A	0.6145	−0.1224	0.8303	0.026*
C15	0.4237 (2)	−0.05849 (10)	0.77768 (9)	0.0235 (4)
H15A	0.3363	−0.0916	0.7874	0.028*
C16	0.3841 (2)	0.00711 (9)	0.73868 (9)	0.0222 (3)
H16A	0.2704	0.0191	0.7222	0.027*
C17	0.9006 (2)	0.06256 (10)	0.67612 (9)	0.0262 (4)
H17A	0.9887	0.0991	0.6700	0.039*
H17B	0.8259	0.0585	0.6279	0.039*
H17C	0.9517	0.0139	0.6892	0.039*
C18	0.9285 (2)	−0.10591 (10)	0.85626 (9)	0.0253 (4)
H18A	1.0505	−0.1078	0.8691	0.038*
H18B	0.8907	−0.1503	0.8265	0.038*
H18C	0.8746	−0.1044	0.9036	0.038*
C19	0.1780 (2)	0.23233 (9)	0.59042 (8)	0.0210 (3)
H19A	0.0886	0.2030	0.6053	0.025*
C20	0.1376 (2)	0.29503 (9)	0.53866 (8)	0.0193 (3)
C21	0.2569 (2)	0.32947 (9)	0.49745 (8)	0.0216 (3)
H21A	0.3706	0.3139	0.5048	0.026*
C22	0.2081 (2)	0.38584 (10)	0.44645 (9)	0.0246 (4)
H22A	0.2887	0.4084	0.4182	0.030*
C23	0.0420 (2)	0.41041 (9)	0.43554 (9)	0.0234 (4)
H23A	0.0103	0.4496	0.4004	0.028*
C24	−0.0767 (2)	0.37737 (9)	0.47628 (9)	0.0209 (3)
C25	−0.02836 (19)	0.31907 (9)	0.52731 (8)	0.0191 (3)
C26	−0.2977 (2)	0.45460 (11)	0.41808 (11)	0.0309 (4)
H26A	−0.4175	0.4637	0.4199	0.046*
H26B	−0.2793	0.4390	0.3661	0.046*
H26C	−0.2347	0.5004	0.4315	0.046*
C27	−0.2600 (2)	0.23775 (10)	0.52664 (9)	0.0273 (4)
H27A	−0.3380	0.2173	0.5603	0.041*
H27B	−0.1981	0.1969	0.5057	0.041*
H27C	−0.3231	0.2652	0.4844	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0249 (6)	0.0233 (6)	0.0214 (5)	0.0023 (5)	0.0017 (4)	0.0007 (4)
O2	0.0256 (6)	0.0275 (7)	0.0292 (6)	−0.0034 (5)	0.0027 (5)	0.0083 (5)
O3	0.0180 (6)	0.0206 (6)	0.0235 (5)	−0.0015 (5)	0.0043 (4)	−0.0011 (4)
O4	0.0182 (6)	0.0238 (6)	0.0262 (6)	0.0018 (5)	−0.0002 (4)	0.0054 (5)
O5	0.0182 (6)	0.0237 (6)	0.0205 (5)	−0.0017 (5)	0.0041 (4)	0.0006 (4)
O6	0.0200 (6)	0.0308 (7)	0.0307 (6)	0.0066 (5)	0.0051 (5)	0.0103 (5)
N1	0.0263 (8)	0.0247 (8)	0.0235 (7)	−0.0004 (6)	0.0086 (6)	0.0015 (6)
N2	0.0227 (7)	0.0229 (7)	0.0232 (7)	0.0017 (6)	0.0017 (5)	0.0029 (5)
N3	0.0223 (7)	0.0206 (7)	0.0225 (7)	0.0019 (6)	0.0012 (5)	0.0020 (5)
C1	0.0254 (9)	0.0215 (9)	0.0222 (8)	0.0028 (7)	0.0065 (6)	−0.0016 (6)
C2	0.0251 (9)	0.0188 (8)	0.0217 (8)	0.0015 (7)	0.0068 (6)	−0.0012 (6)
C3	0.0267 (9)	0.0175 (8)	0.0189 (7)	0.0014 (7)	0.0033 (6)	−0.0028 (6)
C4	0.0237 (9)	0.0213 (9)	0.0227 (8)	−0.0008 (7)	0.0041 (6)	−0.0019 (6)
C5	0.0312 (9)	0.0266 (9)	0.0234 (8)	0.0024 (8)	0.0045 (7)	0.0048 (7)
C6	0.0265 (9)	0.0305 (10)	0.0281 (8)	0.0053 (8)	0.0020 (7)	0.0035 (7)
C7	0.0249 (9)	0.0259 (9)	0.0289 (8)	0.0013 (7)	0.0059 (7)	0.0002 (7)
C8	0.0284 (9)	0.0244 (9)	0.0348 (9)	0.0052 (8)	0.0062 (7)	0.0016 (7)
C9	0.0312 (10)	0.0310 (10)	0.0397 (10)	−0.0009 (8)	0.0086 (8)	0.0133 (8)
C10	0.0196 (8)	0.0220 (8)	0.0182 (7)	−0.0002 (7)	0.0016 (6)	−0.0004 (6)
C11	0.0203 (8)	0.0216 (8)	0.0166 (7)	0.0014 (7)	0.0027 (6)	−0.0019 (6)
C12	0.0192 (8)	0.0196 (8)	0.0174 (7)	−0.0019 (6)	0.0035 (6)	−0.0031 (6)
C13	0.0182 (8)	0.0225 (8)	0.0173 (7)	0.0012 (7)	0.0013 (6)	−0.0026 (6)
C14	0.0249 (8)	0.0205 (8)	0.0203 (7)	0.0008 (7)	0.0038 (6)	0.0018 (6)
C15	0.0212 (8)	0.0258 (9)	0.0241 (8)	−0.0043 (7)	0.0048 (6)	−0.0002 (6)
C16	0.0169 (8)	0.0266 (9)	0.0230 (8)	0.0007 (7)	0.0025 (6)	0.0002 (6)
C17	0.0226 (9)	0.0284 (9)	0.0291 (9)	0.0017 (7)	0.0089 (7)	0.0018 (7)
C18	0.0227 (9)	0.0249 (9)	0.0276 (8)	0.0043 (7)	−0.0002 (6)	0.0064 (7)
C19	0.0206 (8)	0.0221 (9)	0.0203 (7)	0.0004 (7)	0.0030 (6)	−0.0021 (6)
C20	0.0212 (8)	0.0185 (8)	0.0176 (7)	0.0008 (7)	−0.0001 (6)	−0.0027 (6)
C21	0.0184 (8)	0.0244 (9)	0.0217 (8)	−0.0003 (7)	0.0011 (6)	−0.0026 (6)
C22	0.0235 (9)	0.0268 (9)	0.0241 (8)	−0.0041 (7)	0.0058 (6)	0.0004 (7)
C23	0.0247 (9)	0.0231 (9)	0.0221 (8)	0.0011 (7)	0.0019 (6)	0.0046 (6)
C24	0.0189 (8)	0.0228 (9)	0.0211 (7)	0.0021 (7)	0.0021 (6)	−0.0016 (6)
C25	0.0194 (8)	0.0208 (8)	0.0175 (7)	−0.0024 (7)	0.0036 (6)	−0.0020 (6)
C26	0.0245 (9)	0.0291 (10)	0.0385 (10)	0.0055 (8)	0.0012 (7)	0.0116 (8)
C27	0.0224 (9)	0.0302 (10)	0.0288 (9)	−0.0065 (8)	0.0013 (7)	0.0000 (7)

Geometric parameters (Å, º) top

O1—C3	1.3792 (19)	C10—C11	1.465 (2)
O1—C8	1.433 (2)	C10—H10A	0.9500
O2—C4	1.366 (2)	C11—C12	1.397 (2)
O2—C9	1.429 (2)	C11—C16	1.405 (2)
O3—C12	1.3794 (18)	C12—C13	1.403 (2)
O3—C17	1.4383 (19)	C13—C14	1.387 (2)
O4—C13	1.3632 (19)	C14—C15	1.396 (2)
O4—C18	1.4339 (19)	C14—H14A	0.9500
O5—C25	1.3796 (18)	C15—C16	1.380 (2)
O5—C27	1.440 (2)	C15—H15A	0.9500
O6—C24	1.3664 (19)	C16—H16A	0.9500
O6—C26	1.429 (2)	C17—H17A	0.9800
N1—C1	1.283 (2)	C17—H17B	0.9800
N1—N1ⁱ	1.419 (3)	C17—H17C	0.9800
N2—C10	1.276 (2)	C18—H18A	0.9800
N2—N3	1.4146 (19)	C18—H18B	0.9800
N3—C19	1.280 (2)	C18—H18C	0.9800
C1—C2	1.465 (2)	C19—C20	1.458 (2)
C1—H1	0.9500	C19—H19A	0.9500
C2—C3	1.392 (2)	C20—C25	1.393 (2)
C2—C7	1.406 (2)	C20—C21	1.407 (2)
C3—C4	1.406 (2)	C21—C22	1.376 (2)
C4—C5	1.385 (2)	C21—H21A	0.9500
C5—C6	1.391 (2)	C22—C23	1.396 (2)
C5—H5	0.9500	C22—H22A	0.9500
C6—C7	1.379 (2)	C23—C24	1.388 (2)
C6—H6	0.9500	C23—H23A	0.9500
C7—H7	0.9500	C24—C25	1.401 (2)
C8—H8A	0.9800	C26—H26A	0.9800
C8—H8B	0.9800	C26—H26B	0.9800
C8—H8C	0.9800	C26—H26C	0.9800
C9—H9A	0.9800	C27—H27A	0.9800
C9—H9B	0.9800	C27—H27B	0.9800
C9—H9C	0.9800	C27—H27C	0.9800

C3—O1—C8	113.74 (12)	C13—C14—C15	119.57 (15)
C4—O2—C9	117.40 (13)	C13—C14—H14A	120.2
C12—O3—C17	112.88 (12)	C15—C14—H14A	120.2
C13—O4—C18	117.00 (12)	C16—C15—C14	121.34 (15)
C25—O5—C27	113.87 (11)	C16—C15—H15A	119.3
C24—O6—C26	117.17 (13)	C14—C15—H15A	119.3
C1—N1—N1ⁱ	111.08 (16)	C15—C16—C11	119.75 (15)
C10—N2—N3	111.68 (13)	C15—C16—H16A	120.1
C19—N3—N2	110.69 (13)	C11—C16—H16A	120.1
N1—C1—C2	120.95 (15)	O3—C17—H17A	109.5
N1—C1—H1	119.5	O3—C17—H17B	109.5
C2—C1—H1	119.5	H17A—C17—H17B	109.5
C3—C2—C7	119.36 (15)	O3—C17—H17C	109.5
C3—C2—C1	118.68 (15)	H17A—C17—H17C	109.5
C7—C2—C1	121.96 (15)	H17B—C17—H17C	109.5
O1—C3—C2	119.57 (14)	O4—C18—H18A	109.5
O1—C3—C4	119.93 (15)	O4—C18—H18B	109.5
C2—C3—C4	120.45 (15)	H18A—C18—H18B	109.5
O2—C4—C5	125.23 (15)	O4—C18—H18C	109.5
O2—C4—C3	115.20 (14)	H18A—C18—H18C	109.5
C5—C4—C3	119.57 (16)	H18B—C18—H18C	109.5
C4—C5—C6	119.79 (16)	N3—C19—C20	123.12 (15)
C4—C5—H5	120.1	N3—C19—H19A	118.4
C6—C5—H5	120.1	C20—C19—H19A	118.4
C7—C6—C5	121.20 (16)	C25—C20—C21	119.17 (14)
C7—C6—H6	119.4	C25—C20—C19	117.91 (14)
C5—C6—H6	119.4	C21—C20—C19	122.85 (14)
C6—C7—C2	119.61 (16)	C22—C21—C20	119.77 (15)
C6—C7—H7	120.2	C22—C21—H21A	120.1
C2—C7—H7	120.2	C20—C21—H21A	120.1
O1—C8—H8A	109.5	C21—C22—C23	121.09 (15)
O1—C8—H8B	109.5	C21—C22—H22A	119.5
H8A—C8—H8B	109.5	C23—C22—H22A	119.5
O1—C8—H8C	109.5	C24—C23—C22	119.76 (15)
H8A—C8—H8C	109.5	C24—C23—H23A	120.1
H8B—C8—H8C	109.5	C22—C23—H23A	120.1
O2—C9—H9A	109.5	O6—C24—C23	125.21 (14)
O2—C9—H9B	109.5	O6—C24—C25	115.38 (14)
H9A—C9—H9B	109.5	C23—C24—C25	119.41 (15)
O2—C9—H9C	109.5	O5—C25—C20	119.13 (14)
H9A—C9—H9C	109.5	O5—C25—C24	120.00 (14)
H9B—C9—H9C	109.5	C20—C25—C24	120.79 (14)
N2—C10—C11	121.74 (15)	O6—C26—H26A	109.5
N2—C10—H10A	119.1	O6—C26—H26B	109.5
C11—C10—H10A	119.1	H26A—C26—H26B	109.5
C12—C11—C16	118.99 (15)	O6—C26—H26C	109.5
C12—C11—C10	118.67 (14)	H26A—C26—H26C	109.5
C16—C11—C10	122.32 (14)	H26B—C26—H26C	109.5
O3—C12—C11	119.60 (14)	O5—C27—H27A	109.5
O3—C12—C13	119.47 (14)	O5—C27—H27B	109.5
C11—C12—C13	120.88 (14)	H27A—C27—H27B	109.5
O4—C13—C14	125.27 (14)	O5—C27—H27C	109.5
O4—C13—C12	115.25 (14)	H27A—C27—H27C	109.5
C14—C13—C12	119.47 (14)	H27B—C27—H27C	109.5

C10—N2—N3—C19	171.89 (14)	C18—O4—C13—C12	176.95 (13)
N1ⁱ—N1—C1—C2	177.86 (15)	O3—C12—C13—O4	−1.4 (2)
N1—C1—C2—C3	−158.74 (15)	C11—C12—C13—O4	−178.69 (13)
N1—C1—C2—C7	20.1 (2)	O3—C12—C13—C14	177.86 (13)
C8—O1—C3—C2	106.62 (16)	C11—C12—C13—C14	0.5 (2)
C8—O1—C3—C4	−75.95 (18)	O4—C13—C14—C15	178.95 (14)
C7—C2—C3—O1	176.09 (14)	C12—C13—C14—C15	−0.2 (2)
C1—C2—C3—O1	−5.0 (2)	C13—C14—C15—C16	−0.4 (2)
C7—C2—C3—C4	−1.3 (2)	C14—C15—C16—C11	0.6 (2)
C1—C2—C3—C4	177.54 (14)	C12—C11—C16—C15	−0.2 (2)
C9—O2—C4—C5	−3.4 (2)	C10—C11—C16—C15	178.05 (14)
C9—O2—C4—C3	177.07 (15)	N2—N3—C19—C20	−176.19 (13)
O1—C3—C4—O2	3.9 (2)	N3—C19—C20—C25	−165.89 (15)
C2—C3—C4—O2	−178.72 (14)	N3—C19—C20—C21	17.2 (2)
O1—C3—C4—C5	−175.72 (14)	C25—C20—C21—C22	−0.4 (2)
C2—C3—C4—C5	1.7 (2)	C19—C20—C21—C22	176.53 (15)
O2—C4—C5—C6	179.92 (15)	C20—C21—C22—C23	0.9 (2)
C3—C4—C5—C6	−0.5 (2)	C21—C22—C23—C24	−0.4 (2)
C4—C5—C6—C7	−1.0 (3)	C26—O6—C24—C23	2.5 (2)
C5—C6—C7—C2	1.3 (3)	C26—O6—C24—C25	−177.83 (14)
C3—C2—C7—C6	−0.2 (2)	C22—C23—C24—O6	178.95 (15)
C1—C2—C7—C6	−179.01 (15)	C22—C23—C24—C25	−0.7 (2)
N3—N2—C10—C11	−177.09 (13)	C27—O5—C25—C20	−107.31 (16)
N2—C10—C11—C12	−173.93 (14)	C27—O5—C25—C24	75.94 (18)
N2—C10—C11—C16	7.8 (2)	C21—C20—C25—O5	−177.46 (13)
C17—O3—C12—C11	−105.52 (16)	C19—C20—C25—O5	5.5 (2)
C17—O3—C12—C13	77.10 (17)	C21—C20—C25—C24	−0.7 (2)
C16—C11—C12—O3	−177.65 (13)	C19—C20—C25—C24	−177.79 (14)
C10—C11—C12—O3	4.0 (2)	O6—C24—C25—O5	−1.7 (2)
C16—C11—C12—C13	−0.3 (2)	C23—C24—C25—O5	177.97 (14)
C10—C11—C12—C13	−178.66 (13)	O6—C24—C25—C20	−178.42 (13)
C18—O4—C13—C14	−2.2 (2)	C23—C24—C25—C20	1.3 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O3ⁱⁱ	0.98	2.45	3.288 (2)	143
C14—H14A···O5ⁱⁱⁱ	0.95	2.37	3.2890 (19)	161
C18—H18C···O6ⁱⁱⁱ	0.98	2.54	3.5229 (19)	178
C27—H27C···O2^iv	0.98	2.52	3.2656 (19)	133

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₄
M_r	328.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.0294 (2), 17.9415 (5), 17.5258 (4)
β (°)	96.660 (2)
V (Å³)	2507.72 (11)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12722, 5600, 4465
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.03
No. of reflections	5600
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.22

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O3ⁱ	0.98	2.45	3.288 (2)	143
C14—H14A···O5ⁱⁱ	0.95	2.37	3.2890 (19)	161
C18—H18C···O6ⁱⁱ	0.98	2.54	3.5229 (19)	178
C27—H27C···O2ⁱⁱⁱ	0.98	2.52	3.2656 (19)	133

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

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Islam, M. A. A. A. A., Tarafder, M. T. H., Alam, M. A., Guidolin, N. & Zangrando, E. (2009). Acta Cryst. E65, o2560. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar