N-[4-(4-Nitro­phen­oxy)phen­yl]penta­n­amide

Nigar, A.; Akhter, Z.; McKee, V.; Hussain, R.

doi:10.1107/S1600536812036744

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2816

doi:10.1107/S1600536812036744

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N-[4-(4-Nitrophenoxy)phenyl]pentanamide

Asifan Nigar,^a Zareen Akhter,^a ^* Vickie McKee ^b and Rizwan Hussain ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, ^bChemistry Department, Loughborough University, Loughborough LE11 3TU, England, and ^cNESCOM, PO Box 2216, Islamabad, Pakistan
^*Correspondence e-mail: zareenakhter@yahoo.com

(Received 27 July 2012; accepted 24 August 2012; online 31 August 2012)

The asymmetric unit of the title compound, C₁₇H₁₈N₂O₄, contains two independent molecules (A and B) differing principally in the conformations of the alkyl chains, anti for molecule A and gauche for molecule B. The dihedral angles between the aromatic rings are 82.51 (6) and 82.25 (6)° in the two molecules. In the crystal, amide–amide interactions (as N—H⋯O=C) results in distinct chains of A and B molecules running parallel to the a-axis direction. C—H⋯O interactions also occur.

Related literature

For the related structures N-(4-(4-nitrophenoxy)phenyl)propionamide, 4-nitro-N-(4-(4-nitrophenoxy)phenyl)benzamide and N-[4-(4-nitrophenoxy)phenyl]acetamide see: Nigar et al. (2008 ), Butt et al. (2007 ) and Nigar et al. (2012 ), respectively.

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M_r = 314.33
Triclinic, $[P \overline 1]$
a = 4.9776 (5) Å
b = 10.1139 (10) Å
c = 30.572 (3) Å
α = 92.069 (2)°
β = 90.087 (2)°
γ = 91.060 (2)°
V = 1537.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.33 × 0.32 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.968, T_max = 0.987
17614 measured reflections
6018 independent reflections
4664 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.135
S = 1.09
6018 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A1⋯O4Aⁱ	0.88	2.08	2.955 (2)	178
N2B—H2B1⋯O4Bⁱ	0.88	2.05	2.929 (2)	174
C3A—H3A⋯O1Aⁱⁱ	0.95	2.49	3.341 (3)	150
C5A—H5A⋯O2Aⁱⁱⁱ	0.95	2.62	3.376 (3)	137
C3B—H3B⋯O1B^iv	0.95	2.49	3.360 (3)	153
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+3, -z+1; (iv) -x-1, -y, -z.

Data collection: APEX2 (Bruker 1998 ); cell refinement: SAINT (Bruker 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036744/gg2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036744/gg2093Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036744/gg2093Isup3.cml

checkCIF report

Comment top

The crystal structure of N-[4-(4-Nitrophenoxy)phenyl]acetamide (Nigar et al.2012) has been published and is related to that of the title compound, (Fig. 1).

There are two independent molecules in the asymmetric unit, differing primarily in the conformations of the alkyl chains (Fig. 1). The unsaturated sections of the molecules have quite similar orientations, with interplanar angles between the mean planes of the two aromatic rings of 82.51 (6)° for the molecule with 'A' labels and 82.25 (6)° for the molecule with 'B' labels.

Each molecule is linked to two crystallographically identical molecules via H-bonding involving the amide groups (N—H ···O═C distances 2.956 (2) Å and 2.929 (2) Å for N2A···O4A and N2B···O4B respectively, both under symmetry operation x - 1, y, z). This results in separate H-bonded chains of 'A' and 'B' molecules running parallel to the a axis (Fig 2, Table 3).

The nitro groups are involved in weaker H-bonding to aromatic C—H groups. Each molecule 'A' makes four bonds with identical neighbours, linking the chains together (C3A—H···O1A 3.341 (3) Å under -x, 2 - y, 1 - z and C5A—H···O2A 3.376 (3) Å under 1 - x, 3 - y, 1 - z, Fig 3, Table 3). Molecule 'B' only forms one such interaction; C3B···O1B 3.360 (3) Å under -1 - x,-y,-z (Fig 4, Table 3).

Related literature top

For the related structures N-(4-(4-nitrophenoxy)phenyl)propionamide, 4-nitro-N-(4-(4-nitrophenoxy)phenyl)benzamide and N-[4-(4-nitrophenoxy)phenyl]acetamide see: Nigar et al. (2008), Butt et al. (2007) and Nigar et al. (2012), respectively.

Experimental top

Synthesis of N-[4-(4'-Nitrophenoxy)phenyl] pentanamide

A mixture of 2.50 g (25 mmol) 4-aminophenol, 3.46 g (25 mmol) anhydrous K₂CO₃ and 2.65 ml (25 mmol) 4-nitrofluorobenzene in 35 ml DMF was heated at 373 K for 18 h in an inert atmosphere. After cooling to room temperature, the reaction mixture was poured into 400 ml of water to yield a yellow solid. The product was filtered, dried, and then recrystallized from n-hexane (yield, 86%). In the second step, pentanoic acid and thionylchloride were refluxed in equimolar amounts for 30 min. The excessive amount of thionylchloride was rotary evaporated and pentanoylchloride obtained was reacted with 4-(4-nitrophenoxy) aniline, as prepared in the first step, in appropriate molar ratios. THF was used as solvent and 1 ml of triethylamine was also added for 1.0 g of 4-(4-nitrophenoxy) aniline. The reaction mixture was refluxed for 2 h under inert conditions and allowed to stand overnight at room temperature. The settled salt was filtered off and filtrate was evaporated to get the crude product, which was recrystallized from toluene (89% yield, m.p. 390 K)

Computing details top

Data collection: APEX2 (Bruker 1998); cell refinement: SAINT (Bruker 1998); data reduction: SAINT (Bruker 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig 1. Perspective view of the two independent molecules in the asymmetric unit. Thermal ellipsoids shown at the 50% probability level.

Fig 2. Packing diagram showing the NH ··· O ═C H-bonds. Carbon atoms coloured according to symmetry equivalence.

Fig 3. C—H···O interactions between 'A' molecules.

Fig 4. C—H···O interactions between 'B' molecules.

N-[4-(4-Nitrophenoxy)phenyl]pentanamide top

Crystal data top

C₁₇H₁₈N₂O₄	Z = 4
M_r = 314.33	F(000) = 664
Triclinic, P1	D_x = 1.358 Mg m⁻³
Hall symbol: -P 1	Melting point: 390 K
a = 4.9776 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1139 (10) Å	Cell parameters from 4085 reflections
c = 30.572 (3) Å	θ = 2.4–25.3°
α = 92.069 (2)°	µ = 0.10 mm⁻¹
β = 90.087 (2)°	T = 150 K
γ = 91.060 (2)°	Wedge, brown
V = 1537.8 (3) Å³	0.33 × 0.32 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	6018 independent reflections
Radiation source: fine-focus sealed tube	4664 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 26.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −6→6
T_min = 0.968, T_max = 0.987	k = −12→12
17614 measured reflections	l = −37→37

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0389P)² + 1.2455P] where P = (F_o² + 2F_c²)/3
6018 reflections	(Δ/σ)_max < 0.001
415 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₄	γ = 91.060 (2)°
M_r = 314.33	V = 1537.8 (3) Å³
Triclinic, P1	Z = 4
a = 4.9776 (5) Å	Mo Kα radiation
b = 10.1139 (10) Å	µ = 0.10 mm⁻¹
c = 30.572 (3) Å	T = 150 K
α = 92.069 (2)°	0.33 × 0.32 × 0.13 mm
β = 90.087 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6018 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	4664 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.987	R_int = 0.033
17614 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.09	Δρ_max = 0.34 e Å⁻³
6018 reflections	Δρ_min = −0.21 e Å⁻³
415 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
C1A	0.6952 (5)	1.1513 (2)	0.41515 (8)	0.0331 (5)
C2A	0.5007 (5)	1.0629 (2)	0.42860 (8)	0.0323 (5)
H2A	0.4789	0.9789	0.4140	0.039*
C3A	0.3375 (5)	1.0977 (2)	0.46368 (8)	0.0330 (5)
H3A	0.2037	1.0377	0.4736	0.040*
C4A	0.3722 (5)	1.2207 (2)	0.48397 (7)	0.0313 (5)
N1A	0.1898 (4)	1.2606 (2)	0.51924 (7)	0.0387 (5)
O1A	0.0553 (4)	1.17409 (19)	0.53686 (6)	0.0511 (5)
O2A	0.1772 (4)	1.37879 (18)	0.52958 (6)	0.0489 (5)
C5A	0.5702 (5)	1.3092 (2)	0.47140 (8)	0.0350 (5)
H5A	0.5933	1.3926	0.4864	0.042*
C6A	0.7335 (5)	1.2738 (2)	0.43667 (8)	0.0357 (5)
H6A	0.8713	1.3327	0.4275	0.043*
O3A	0.8658 (3)	1.12568 (18)	0.38088 (6)	0.0442 (5)
C7A	0.7902 (5)	1.0268 (2)	0.34970 (8)	0.0349 (5)
C8A	0.5830 (5)	1.0467 (2)	0.32109 (8)	0.0394 (6)
H8A	0.4787	1.1242	0.3240	0.047*
C9A	0.5272 (5)	0.9532 (2)	0.28806 (8)	0.0360 (6)
H9A	0.3832	0.9663	0.2683	0.043*
C10A	0.6800 (4)	0.8405 (2)	0.28355 (7)	0.0278 (5)
C11A	0.8841 (5)	0.8202 (2)	0.31316 (8)	0.0377 (6)
H11A	0.9872	0.7422	0.3107	0.045*
C12A	0.9385 (5)	0.9137 (3)	0.34648 (8)	0.0417 (6)
H12A	1.0777	0.8996	0.3670	0.050*
N2A	0.6189 (4)	0.74848 (19)	0.24853 (6)	0.0305 (4)
H2A1	0.4481	0.7321	0.2427	0.037*
C13A	0.8018 (4)	0.6841 (2)	0.22349 (7)	0.0295 (5)
O4A	1.0444 (3)	0.68820 (17)	0.23109 (5)	0.0367 (4)
C14A	0.6836 (5)	0.6108 (3)	0.18369 (8)	0.0380 (6)
H14A	0.5192	0.5624	0.1926	0.046*
H14B	0.6300	0.6763	0.1622	0.046*
C15A	0.8712 (5)	0.5141 (3)	0.16170 (8)	0.0371 (6)
H15A	0.9136	0.4442	0.1823	0.044*
H15B	1.0413	0.5609	0.1546	0.044*
C16A	0.7546 (5)	0.4497 (3)	0.11993 (8)	0.0393 (6)
H16A	0.7300	0.5180	0.0980	0.047*
H16B	0.5762	0.4100	0.1262	0.047*
C17A	0.9380 (6)	0.3430 (3)	0.10128 (10)	0.0523 (7)
H17A	0.8580	0.3032	0.0745	0.078*
H17B	0.9603	0.2746	0.1228	0.078*
H17C	1.1137	0.3824	0.0945	0.078*
C1B	0.1775 (5)	−0.1421 (2)	0.09199 (8)	0.0355 (5)
C2B	0.0018 (5)	−0.0524 (2)	0.07505 (8)	0.0355 (5)
H2B	−0.0041	0.0355	0.0870	0.043*
C3B	−0.1649 (5)	−0.0917 (2)	0.04060 (8)	0.0367 (6)
H3B	−0.2868	−0.0314	0.0287	0.044*
C4B	−0.1514 (5)	−0.2198 (2)	0.02386 (8)	0.0358 (5)
N1B	−0.3357 (5)	−0.2628 (2)	−0.01144 (7)	0.0452 (5)
O1B	−0.4575 (5)	−0.1779 (2)	−0.03068 (7)	0.0630 (6)
O2B	−0.3609 (4)	−0.3815 (2)	−0.02012 (7)	0.0585 (6)
C5B	0.0274 (5)	−0.3092 (2)	0.03978 (8)	0.0403 (6)
H5B	0.0347	−0.3966	0.0274	0.048*
C6B	0.1945 (5)	−0.2697 (3)	0.07381 (9)	0.0417 (6)
H6B	0.3210	−0.3293	0.0849	0.050*
O3B	0.3504 (4)	−0.11092 (19)	0.12585 (6)	0.0511 (5)
C7B	0.2903 (5)	−0.0041 (2)	0.15468 (8)	0.0374 (6)
C8B	0.0770 (5)	−0.0121 (3)	0.18294 (8)	0.0414 (6)
H8B	−0.0434	−0.0861	0.1812	0.050*
C9B	0.0393 (5)	0.0892 (2)	0.21400 (8)	0.0364 (6)
H9B	−0.1091	0.0848	0.2334	0.044*
C10B	0.2158 (4)	0.1966 (2)	0.21698 (7)	0.0292 (5)
C11B	0.4253 (5)	0.2041 (3)	0.18721 (8)	0.0383 (6)
H11B	0.5443	0.2787	0.1883	0.046*
C12B	0.4618 (5)	0.1036 (3)	0.15602 (8)	0.0429 (6)
H12B	0.6050	0.1092	0.1356	0.051*
N2B	0.1717 (4)	0.29683 (19)	0.24937 (6)	0.0318 (4)
H2B1	0.0035	0.3139	0.2560	0.038*
C13B	0.3637 (4)	0.3693 (2)	0.27129 (7)	0.0313 (5)
O4B	0.6048 (3)	0.35562 (18)	0.26473 (6)	0.0424 (4)
C14B	0.2633 (5)	0.4669 (2)	0.30584 (8)	0.0359 (6)
H14C	0.0654	0.4723	0.3036	0.043*
H14D	0.3410	0.5557	0.3006	0.043*
C15B	0.3385 (5)	0.4267 (3)	0.35172 (8)	0.0417 (6)
H15C	0.5355	0.4158	0.3533	0.050*
H15D	0.2522	0.3401	0.3575	0.050*
C16B	0.2540 (5)	0.5274 (3)	0.38710 (8)	0.0402 (6)
H16C	0.0604	0.5449	0.3834	0.048*
H16D	0.2775	0.4882	0.4160	0.048*
C17B	0.4077 (5)	0.6579 (3)	0.38696 (9)	0.0447 (6)
H17D	0.3405	0.7170	0.4104	0.067*
H17E	0.3830	0.6988	0.3587	0.067*
H17F	0.5992	0.6424	0.3917	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0290 (12)	0.0373 (13)	0.0328 (12)	0.0016 (10)	−0.0005 (10)	−0.0023 (10)
C2A	0.0350 (13)	0.0281 (12)	0.0333 (13)	0.0004 (10)	−0.0023 (10)	−0.0051 (10)
C3A	0.0340 (12)	0.0312 (12)	0.0338 (13)	−0.0013 (10)	−0.0010 (10)	0.0006 (10)
C4A	0.0317 (12)	0.0334 (12)	0.0287 (12)	0.0056 (10)	−0.0030 (9)	−0.0021 (9)
N1A	0.0404 (12)	0.0429 (13)	0.0325 (11)	0.0060 (10)	−0.0006 (9)	−0.0043 (9)
O1A	0.0585 (12)	0.0512 (12)	0.0433 (11)	−0.0046 (10)	0.0158 (9)	−0.0016 (9)
O2A	0.0591 (12)	0.0395 (11)	0.0473 (11)	0.0092 (9)	0.0072 (9)	−0.0122 (8)
C5A	0.0384 (13)	0.0292 (12)	0.0369 (13)	0.0012 (10)	−0.0039 (10)	−0.0056 (10)
C6A	0.0335 (13)	0.0324 (13)	0.0406 (14)	−0.0040 (10)	−0.0011 (10)	−0.0041 (10)
O3A	0.0358 (9)	0.0478 (11)	0.0471 (11)	−0.0099 (8)	0.0101 (8)	−0.0188 (8)
C7A	0.0294 (12)	0.0403 (14)	0.0340 (13)	−0.0053 (10)	0.0063 (10)	−0.0085 (10)
C8A	0.0432 (14)	0.0351 (13)	0.0399 (14)	0.0108 (11)	0.0033 (11)	−0.0010 (11)
C9A	0.0318 (12)	0.0428 (14)	0.0338 (13)	0.0086 (10)	−0.0025 (10)	0.0028 (11)
C10A	0.0234 (11)	0.0339 (12)	0.0260 (11)	−0.0025 (9)	0.0020 (9)	0.0001 (9)
C11A	0.0344 (13)	0.0391 (14)	0.0392 (14)	0.0100 (10)	−0.0067 (11)	−0.0070 (11)
C12A	0.0309 (13)	0.0523 (16)	0.0410 (14)	0.0042 (11)	−0.0082 (11)	−0.0110 (12)
N2A	0.0191 (9)	0.0385 (11)	0.0336 (10)	−0.0009 (8)	−0.0017 (8)	−0.0033 (8)
C13A	0.0227 (11)	0.0336 (12)	0.0321 (12)	−0.0008 (9)	−0.0020 (9)	0.0016 (10)
O4A	0.0223 (8)	0.0474 (10)	0.0398 (10)	0.0009 (7)	−0.0026 (7)	−0.0088 (8)
C14A	0.0256 (12)	0.0470 (15)	0.0408 (14)	0.0009 (10)	−0.0061 (10)	−0.0076 (11)
C15A	0.0294 (12)	0.0443 (14)	0.0371 (13)	−0.0013 (10)	−0.0028 (10)	−0.0035 (11)
C16A	0.0329 (13)	0.0474 (15)	0.0368 (14)	−0.0040 (11)	−0.0045 (10)	−0.0050 (11)
C17A	0.0418 (15)	0.0628 (19)	0.0507 (17)	0.0022 (13)	−0.0084 (13)	−0.0196 (14)
C1B	0.0318 (12)	0.0384 (14)	0.0361 (13)	0.0053 (10)	−0.0003 (10)	−0.0036 (10)
C2B	0.0369 (13)	0.0302 (12)	0.0391 (14)	0.0046 (10)	0.0012 (10)	−0.0042 (10)
C3B	0.0386 (13)	0.0372 (13)	0.0343 (13)	0.0054 (11)	0.0003 (10)	−0.0006 (10)
C4B	0.0372 (13)	0.0385 (14)	0.0312 (13)	−0.0057 (11)	0.0029 (10)	−0.0001 (10)
N1B	0.0473 (13)	0.0493 (14)	0.0383 (12)	−0.0052 (11)	−0.0008 (10)	−0.0044 (11)
O1B	0.0697 (14)	0.0609 (14)	0.0582 (13)	0.0056 (11)	−0.0255 (11)	−0.0036 (11)
O2B	0.0713 (14)	0.0471 (12)	0.0557 (13)	−0.0152 (10)	−0.0069 (10)	−0.0106 (10)
C5B	0.0498 (15)	0.0301 (13)	0.0405 (14)	0.0019 (11)	0.0043 (12)	−0.0044 (11)
C6B	0.0457 (15)	0.0366 (14)	0.0429 (15)	0.0117 (11)	−0.0014 (12)	−0.0033 (11)
O3B	0.0468 (11)	0.0528 (12)	0.0528 (12)	0.0211 (9)	−0.0167 (9)	−0.0187 (9)
C7B	0.0359 (13)	0.0403 (14)	0.0360 (13)	0.0123 (11)	−0.0075 (11)	−0.0065 (11)
C8B	0.0425 (15)	0.0413 (15)	0.0406 (14)	−0.0049 (11)	−0.0045 (11)	0.0050 (11)
C9B	0.0326 (13)	0.0442 (14)	0.0323 (13)	−0.0020 (11)	0.0025 (10)	0.0030 (11)
C10B	0.0245 (11)	0.0353 (12)	0.0280 (12)	0.0071 (9)	−0.0026 (9)	0.0021 (9)
C11B	0.0311 (13)	0.0444 (15)	0.0388 (14)	−0.0041 (11)	0.0050 (10)	−0.0057 (11)
C12B	0.0301 (13)	0.0611 (17)	0.0366 (14)	0.0025 (12)	0.0051 (10)	−0.0111 (12)
N2B	0.0216 (9)	0.0440 (12)	0.0297 (10)	0.0067 (8)	0.0025 (8)	−0.0014 (9)
C13B	0.0259 (12)	0.0376 (13)	0.0304 (12)	0.0052 (10)	−0.0011 (9)	−0.0004 (10)
O4B	0.0221 (8)	0.0595 (12)	0.0445 (10)	0.0046 (8)	0.0008 (7)	−0.0129 (9)
C14B	0.0298 (12)	0.0402 (14)	0.0378 (14)	0.0096 (10)	−0.0015 (10)	−0.0035 (11)
C15B	0.0467 (15)	0.0408 (14)	0.0382 (14)	0.0114 (12)	0.0052 (11)	0.0019 (11)
C16B	0.0427 (14)	0.0446 (15)	0.0337 (13)	0.0106 (11)	0.0067 (11)	−0.0003 (11)
C17B	0.0429 (15)	0.0489 (16)	0.0418 (15)	0.0079 (12)	−0.0005 (12)	−0.0061 (12)

Geometric parameters (Å, º) top

C1A—O3A	1.370 (3)	C1B—O3B	1.369 (3)
C1A—C2A	1.379 (3)	C1B—C2B	1.385 (3)
C1A—C6A	1.391 (3)	C1B—C6B	1.390 (3)
C2A—C3A	1.386 (3)	C2B—C3B	1.382 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.378 (3)	C3B—C4B	1.378 (3)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.383 (3)	C4B—C5B	1.381 (3)
C4A—N1A	1.461 (3)	C4B—N1B	1.464 (3)
N1A—O2A	1.229 (3)	N1B—O2B	1.225 (3)
N1A—O1A	1.232 (3)	N1B—O1B	1.227 (3)
C5A—C6A	1.379 (3)	C5B—C6B	1.374 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—H6A	0.9500	C6B—H6B	0.9500
O3A—C7A	1.403 (3)	O3B—C7B	1.406 (3)
C7A—C12A	1.373 (3)	C7B—C12B	1.371 (4)
C7A—C8A	1.373 (3)	C7B—C8B	1.373 (4)
C8A—C9A	1.383 (3)	C8B—C9B	1.387 (4)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.385 (3)	C9B—C10B	1.385 (3)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.383 (3)	C10B—C11B	1.388 (3)
C10A—N2A	1.422 (3)	C10B—N2B	1.412 (3)
C11A—C12A	1.387 (3)	C11B—C12B	1.383 (3)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
N2A—C13A	1.352 (3)	N2B—C13B	1.355 (3)
N2A—H2A1	0.8800	N2B—H2B1	0.8800
C13A—O4A	1.229 (3)	C13B—O4B	1.227 (3)
C13A—C14A	1.514 (3)	C13B—C14B	1.512 (3)
C14A—C15A	1.506 (3)	C14B—C15B	1.522 (3)
C14A—H14A	0.9900	C14B—H14C	0.9900
C14A—H14B	0.9900	C14B—H14D	0.9900
C15A—C16A	1.522 (3)	C15B—C16B	1.524 (3)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—C17A	1.522 (4)	C16B—C17B	1.513 (4)
C16A—H16A	0.9900	C16B—H16C	0.9900
C16A—H16B	0.9900	C16B—H16D	0.9900
C17A—H17A	0.9800	C17B—H17D	0.9800
C17A—H17B	0.9800	C17B—H17E	0.9800
C17A—H17C	0.9800	C17B—H17F	0.9800

O3A—C1A—C2A	123.5 (2)	O3B—C1B—C2B	123.2 (2)
O3A—C1A—C6A	115.3 (2)	O3B—C1B—C6B	116.0 (2)
C2A—C1A—C6A	121.2 (2)	C2B—C1B—C6B	120.8 (2)
C1A—C2A—C3A	119.4 (2)	C3B—C2B—C1B	119.5 (2)
C1A—C2A—H2A	120.3	C3B—C2B—H2B	120.2
C3A—C2A—H2A	120.3	C1B—C2B—H2B	120.2
C4A—C3A—C2A	119.0 (2)	C4B—C3B—C2B	118.9 (2)
C4A—C3A—H3A	120.5	C4B—C3B—H3B	120.5
C2A—C3A—H3A	120.5	C2B—C3B—H3B	120.5
C3A—C4A—C5A	122.2 (2)	C3B—C4B—C5B	122.1 (2)
C3A—C4A—N1A	119.0 (2)	C3B—C4B—N1B	118.8 (2)
C5A—C4A—N1A	118.8 (2)	C5B—C4B—N1B	119.1 (2)
O2A—N1A—O1A	123.4 (2)	O2B—N1B—O1B	123.5 (2)
O2A—N1A—C4A	118.3 (2)	O2B—N1B—C4B	118.3 (2)
O1A—N1A—C4A	118.4 (2)	O1B—N1B—C4B	118.2 (2)
C6A—C5A—C4A	118.6 (2)	C6B—C5B—C4B	118.9 (2)
C6A—C5A—H5A	120.7	C6B—C5B—H5B	120.5
C4A—C5A—H5A	120.7	C4B—C5B—H5B	120.5
C5A—C6A—C1A	119.6 (2)	C5B—C6B—C1B	119.7 (2)
C5A—C6A—H6A	120.2	C5B—C6B—H6B	120.1
C1A—C6A—H6A	120.2	C1B—C6B—H6B	120.1
C1A—O3A—C7A	118.14 (18)	C1B—O3B—C7B	118.86 (18)
C12A—C7A—C8A	120.8 (2)	C12B—C7B—C8B	121.1 (2)
C12A—C7A—O3A	118.7 (2)	C12B—C7B—O3B	118.1 (2)
C8A—C7A—O3A	120.4 (2)	C8B—C7B—O3B	120.6 (2)
C7A—C8A—C9A	119.6 (2)	C7B—C8B—C9B	119.2 (2)
C7A—C8A—H8A	120.2	C7B—C8B—H8B	120.4
C9A—C8A—H8A	120.2	C9B—C8B—H8B	120.4
C8A—C9A—C10A	120.4 (2)	C10B—C9B—C8B	120.7 (2)
C8A—C9A—H9A	119.8	C10B—C9B—H9B	119.7
C10A—C9A—H9A	119.8	C8B—C9B—H9B	119.7
C11A—C10A—C9A	119.5 (2)	C9B—C10B—C11B	119.0 (2)
C11A—C10A—N2A	122.2 (2)	C9B—C10B—N2B	118.8 (2)
C9A—C10A—N2A	118.4 (2)	C11B—C10B—N2B	122.2 (2)
C10A—C11A—C12A	120.1 (2)	C12B—C11B—C10B	120.3 (2)
C10A—C11A—H11A	120.0	C12B—C11B—H11B	119.8
C12A—C11A—H11A	120.0	C10B—C11B—H11B	119.8
C7A—C12A—C11A	119.7 (2)	C7B—C12B—C11B	119.7 (2)
C7A—C12A—H12A	120.1	C7B—C12B—H12B	120.2
C11A—C12A—H12A	120.1	C11B—C12B—H12B	120.2
C13A—N2A—C10A	125.31 (18)	C13B—N2B—C10B	126.19 (18)
C13A—N2A—H2A1	117.3	C13B—N2B—H2B1	116.9
C10A—N2A—H2A1	117.3	C10B—N2B—H2B1	116.9
O4A—C13A—N2A	123.5 (2)	O4B—C13B—N2B	123.0 (2)
O4A—C13A—C14A	122.4 (2)	O4B—C13B—C14B	121.2 (2)
N2A—C13A—C14A	114.11 (19)	N2B—C13B—C14B	115.74 (19)
C15A—C14A—C13A	114.24 (19)	C13B—C14B—C15B	111.66 (19)
C15A—C14A—H14A	108.7	C13B—C14B—H14C	109.3
C13A—C14A—H14A	108.7	C15B—C14B—H14C	109.3
C15A—C14A—H14B	108.7	C13B—C14B—H14D	109.3
C13A—C14A—H14B	108.7	C15B—C14B—H14D	109.3
H14A—C14A—H14B	107.6	H14C—C14B—H14D	107.9
C14A—C15A—C16A	113.0 (2)	C14B—C15B—C16B	112.8 (2)
C14A—C15A—H15A	109.0	C14B—C15B—H15C	109.0
C16A—C15A—H15A	109.0	C16B—C15B—H15C	109.0
C14A—C15A—H15B	109.0	C14B—C15B—H15D	109.0
C16A—C15A—H15B	109.0	C16B—C15B—H15D	109.0
H15A—C15A—H15B	107.8	H15C—C15B—H15D	107.8
C15A—C16A—C17A	111.2 (2)	C17B—C16B—C15B	114.6 (2)
C15A—C16A—H16A	109.4	C17B—C16B—H16C	108.6
C17A—C16A—H16A	109.4	C15B—C16B—H16C	108.6
C15A—C16A—H16B	109.4	C17B—C16B—H16D	108.6
C17A—C16A—H16B	109.4	C15B—C16B—H16D	108.6
H16A—C16A—H16B	108.0	H16C—C16B—H16D	107.6
C16A—C17A—H17A	109.5	C16B—C17B—H17D	109.5
C16A—C17A—H17B	109.5	C16B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C16A—C17A—H17C	109.5	C16B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A1···O4Aⁱ	0.88	2.08	2.955 (2)	178
N2B—H2B1···O4Bⁱ	0.88	2.05	2.929 (2)	174
C3A—H3A···O1Aⁱⁱ	0.95	2.49	3.341 (3)	150
C5A—H5A···O2Aⁱⁱⁱ	0.95	2.62	3.376 (3)	137
C3B—H3B···O1B^iv	0.95	2.49	3.360 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄
M_r	314.33
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	4.9776 (5), 10.1139 (10), 30.572 (3)
α, β, γ (°)	92.069 (2), 90.087 (2), 91.060 (2)
V (Å³)	1537.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.32 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.968, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17614, 6018, 4664
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.135, 1.09
No. of reflections	6018
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: APEX2 (Bruker 1998), SAINT (Bruker 1998), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A1···O4Aⁱ	0.88	2.08	2.955 (2)	178
N2B—H2B1···O4Bⁱ	0.88	2.05	2.929 (2)	174
C3A—H3A···O1Aⁱⁱ	0.95	2.49	3.341 (3)	150
C5A—H5A···O2Aⁱⁱⁱ	0.95	2.62	3.376 (3)	137
C3B—H3B···O1B^iv	0.95	2.49	3.360 (3)	153

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

Acknowledgements

The authors are grateful to the Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and the Chemistry Department, Loughborough University, Loughborough, England, for providing laboratory and analytical facilities.

References

Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butt, M. S., Akhter, Z., Bolte, M., Siddiqi, H. M. & Shamsi, E. (2007). Acta Cryst. E63, o476–o478. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nigar, A., Akhter, Z., Bolte, M., Siddiqi, H. M. & Hussain, R. (2008). Acta Cryst. E64, o2186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nigar, A., Akhter, Z. & Tahir, M. N. (2012). Acta Cryst. E68, o2485. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar