1,3-Dicyclo­hexyl-1-(4-nitro­benzo­yl)urea

Dhinaa, A.N.; Jagan, R.; Sivakumar, K.; Chinnakali, K.

doi:10.1107/S1600536810016107

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1291

https://doi.org/10.1107/S1600536810016107

Open

access

1,3-Dicyclohexyl-1-(4-nitrobenzoyl)urea

A. N. Dhinaa,^a R. Jagan,^a K. Sivakumar ^a and K. Chinnakali ^a ^*

^aDepartment of Physics, Anna University Chennai, Chennai 600 025, India
^*Correspondence e-mail: kali@annauniv.edu

(Received 29 April 2010; accepted 1 May 2010; online 8 May 2010)

In the title compound, C₂₀H₂₇N₃O₄, both cyclohexane rings adopt chair conformations. The benzene ring and the amide group are oriented at a dihedral angle of 62.1 (2)°. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains propagating in [010], which contain R₂²(12) ring motifs.

Related literature

For the biological activity of benzoylurea and N-aroylurea derivatives, see: Song et al. (2008 , 2009 ); Amornraksa et al. (2009 ). For related N-benzoyl-N,N′-dicyclohexylurea structures, see: Orea Flores et al. (2006 ); Wang & Peng (2008 ).

Experimental

Crystal data

C₂₀H₂₇N₃O₄
M_r = 373.45
Monoclinic, C 2/c
a = 25.294 (2) Å
b = 9.5757 (7) Å
c = 16.6943 (14) Å
β = 105.140 (2)°
V = 3903.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ) T_min = 0.836, T_max = 0.982
22623 measured reflections
5012 independent reflections
3152 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 1.02
5012 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.10	2.9396 (15)	166
C1—H1⋯O2ⁱⁱ	0.98	2.43	3.3636 (18)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016107/hb5432sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016107/hb5432Isup2.hkl

checkCIF report

Comment top

Benzoylurea derivatives act as antimitotic (Song et al., 2008) and antiproliferative (Song et al., 2009) agents. Some of the N-aroylurea analogs have been found to exhibit antioxidant activity (Amornraksa et al., 2009). We report here the crystal structure of the title compound, (I), an aroylurea.

In the title molecule (Fig. 1), both cyclohexane rings adopt chair conformations. The benzoyl carbonyl group is twisted away from the N–H group and as a result no intramolecular N—H···O hydrogen bond is formed. The dihedral angle between the N1/C7/O1 and N2/C14/O2 planes is 65.0 (2)°. The amide group (C7/O1/N1) and the benzene ring (C15–C20) are oriented at a dihedral angle of 62.1 (1)°. The nitro group is almost coplanar with the attached benzene ring [C19—C18—N3—O3 = -0.8 (3)° and C17—C18—N3—O4 = -1.6 (3)°]. Bond lengths and angles are comparable to those observed in N-benzoyl-N,N'-dicyclohexylurea (Orea Flores et al., 2006) and N-(4-bromobenzoyl)-N,N-dicyclohexylurea (Wang & Peng, 2008).

In the crystal structure, N1—H1A···O1ⁱ and C1—H1···O2ⁱⁱ hydrogen bonds (symmetry codes as in Table 1) generate R²₂(12) ring motifs which are fused into a ribbon-like structure along the b axis (Fig.2).

Related literature top

For the biological activity of benzoylurea and N-aroylurea derivatives, see: Song et al. (2008, 2009); Amornraksa et al. (2009). For related N-benzoyl-N,N'-dicyclohexylurea structures, see: Orea Flores et al. (2006); Wang & Peng (2008).

Experimental top

4-Nitrobenzoic acid (1 g, 5.9 mmol) and dicyclohexylcarbodiimide (1.203 g, 5.9 mmol) were dissolved in dichloromethane (30 ml). The resulting mixture was stirred overnight and then the solvent was removed by rotary evaporator. The product was isolated by column chromatography by using ethyl acetate-hexane (1:9) as eluent. Pale yellow blocks of (I) were obtained by slow evaporation of an ethanolic solution over a period of two weeks.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing fused R²₂(12) ring motifs generating a molecular ribbon extending along the b axis.

1,3-Dicyclohexyl-1-(4-nitrobenzoyl)urea top

Crystal data top

C₂₀H₂₇N₃O₄	F(000) = 1600
M_r = 373.45	D_x = 1.271 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4827 reflections
a = 25.294 (2) Å	θ = 2.5–23.4°
b = 9.5757 (7) Å	µ = 0.09 mm⁻¹
c = 16.6943 (14) Å	T = 292 K
β = 105.140 (2)°	Block, pale-yellow
V = 3903.1 (5) Å³	0.25 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	5012 independent reflections
Radiation source: fine-focus sealed tube	3152 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and φ scan	θ_max = 28.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −34→34
T_min = 0.836, T_max = 0.982	k = −12→12
22623 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0549P)² + 1.482P] where P = (F_o² + 2F_c²)/3
5012 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₀H₂₇N₃O₄	V = 3903.1 (5) Å³
M_r = 373.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.294 (2) Å	µ = 0.09 mm⁻¹
b = 9.5757 (7) Å	T = 292 K
c = 16.6943 (14) Å	0.25 × 0.20 × 0.20 mm
β = 105.140 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 1999)	3152 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.982	R_int = 0.031
22623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
5012 reflections	Δρ_min = −0.14 e Å⁻³
244 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
C1	0.18614 (6)	0.20858 (14)	0.12793 (9)	0.0419 (3)
H1	0.1969	0.1116	0.1220	0.050*
C2	0.12619 (7)	0.2094 (2)	0.12851 (11)	0.0651 (5)
H2A	0.1151	0.3039	0.1374	0.078*
H2B	0.1212	0.1517	0.1738	0.078*
C3	0.09045 (7)	0.1538 (3)	0.04623 (12)	0.0795 (6)
H3A	0.0991	0.0563	0.0402	0.095*
H3B	0.0522	0.1596	0.0466	0.095*
C4	0.09915 (8)	0.2346 (2)	−0.02572 (12)	0.0786 (6)
H4A	0.0870	0.3301	−0.0228	0.094*
H4B	0.0775	0.1938	−0.0770	0.094*
C5	0.15886 (8)	0.2338 (2)	−0.02557 (11)	0.0713 (5)
H5A	0.1638	0.2902	−0.0713	0.086*
H5B	0.1700	0.1391	−0.0337	0.086*
C6	0.19480 (8)	0.29061 (19)	0.05559 (10)	0.0603 (4)
H6A	0.2330	0.2850	0.0549	0.072*
H6B	0.1860	0.3880	0.0615	0.072*
C7	0.25502 (6)	0.18506 (14)	0.26110 (9)	0.0405 (3)
C8	0.34370 (6)	0.27308 (16)	0.35126 (10)	0.0511 (4)
H8	0.3545	0.3551	0.3869	0.061*
C9	0.36104 (7)	0.2997 (2)	0.27233 (12)	0.0665 (5)
H9A	0.3436	0.3841	0.2460	0.080*
H9B	0.3492	0.2226	0.2341	0.080*
C10	0.42312 (8)	0.3153 (3)	0.29111 (15)	0.0843 (6)
H10A	0.4335	0.3269	0.2396	0.101*
H10B	0.4345	0.3982	0.3246	0.101*
C11	0.45178 (8)	0.1898 (3)	0.33654 (17)	0.0955 (8)
H11A	0.4911	0.2037	0.3493	0.115*
H11B	0.4427	0.1081	0.3013	0.115*
C12	0.43525 (8)	0.1653 (3)	0.41589 (16)	0.1003 (8)
H12A	0.4471	0.2434	0.4532	0.120*
H12B	0.4531	0.0817	0.4428	0.120*
C13	0.37307 (7)	0.1487 (2)	0.39846 (13)	0.0748 (6)
H13A	0.3617	0.0644	0.3663	0.090*
H13B	0.3631	0.1393	0.4505	0.090*
C14	0.25633 (7)	0.32416 (15)	0.38509 (9)	0.0478 (4)
C15	0.19665 (6)	0.29435 (15)	0.37139 (9)	0.0462 (3)
C16	0.16036 (8)	0.40464 (17)	0.36337 (13)	0.0689 (5)
H16	0.1732	0.4956	0.3632	0.083*
C17	0.10558 (9)	0.3818 (2)	0.35558 (14)	0.0784 (6)
H17	0.0811	0.4560	0.3489	0.094*
C18	0.08794 (7)	0.2471 (2)	0.35787 (11)	0.0611 (4)
C19	0.12263 (7)	0.13583 (19)	0.36631 (11)	0.0599 (4)
H19	0.1095	0.0453	0.3674	0.072*
C20	0.17750 (7)	0.15920 (16)	0.37322 (10)	0.0521 (4)
H20	0.2016	0.0842	0.3791	0.063*
N1	0.22096 (5)	0.26334 (11)	0.20560 (7)	0.0426 (3)
H1A	0.2192	0.3510	0.2157	0.051*
N2	0.28337 (5)	0.25964 (12)	0.33451 (7)	0.0450 (3)
N3	0.02944 (8)	0.2204 (3)	0.35113 (12)	0.0897 (6)
O1	0.26427 (4)	0.06149 (10)	0.25260 (6)	0.0535 (3)
O2	0.27950 (5)	0.40101 (12)	0.44180 (7)	0.0660 (3)
O3	0.01453 (7)	0.1016 (3)	0.35244 (15)	0.1366 (8)
O4	−0.00053 (8)	0.3209 (3)	0.34562 (14)	0.1356 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0420 (8)	0.0411 (7)	0.0381 (8)	0.0019 (6)	0.0026 (6)	−0.0032 (6)
C2	0.0507 (10)	0.0968 (13)	0.0464 (10)	−0.0144 (9)	0.0101 (8)	−0.0049 (9)
C3	0.0459 (10)	0.1293 (18)	0.0568 (12)	−0.0117 (11)	0.0016 (8)	−0.0154 (12)
C4	0.0766 (14)	0.0941 (14)	0.0491 (11)	0.0318 (11)	−0.0122 (9)	−0.0059 (10)
C5	0.0924 (15)	0.0818 (12)	0.0369 (9)	−0.0024 (10)	0.0122 (9)	0.0032 (8)
C6	0.0683 (11)	0.0700 (10)	0.0455 (9)	−0.0077 (9)	0.0199 (8)	−0.0026 (8)
C7	0.0382 (7)	0.0415 (7)	0.0391 (8)	−0.0064 (6)	0.0052 (6)	−0.0011 (6)
C8	0.0437 (8)	0.0566 (8)	0.0464 (9)	−0.0144 (7)	0.0000 (7)	−0.0014 (7)
C9	0.0496 (10)	0.0845 (12)	0.0617 (11)	−0.0081 (9)	0.0079 (8)	0.0146 (9)
C10	0.0558 (12)	0.1142 (17)	0.0825 (15)	−0.0205 (11)	0.0175 (10)	0.0039 (13)
C11	0.0434 (11)	0.1230 (19)	0.109 (2)	−0.0024 (12)	−0.0003 (11)	−0.0069 (16)
C12	0.0559 (12)	0.1229 (19)	0.1000 (19)	−0.0031 (12)	−0.0191 (12)	0.0269 (15)
C13	0.0529 (11)	0.0874 (13)	0.0695 (13)	−0.0088 (9)	−0.0099 (9)	0.0259 (10)
C14	0.0610 (10)	0.0460 (7)	0.0338 (8)	−0.0122 (7)	0.0075 (7)	0.0021 (6)
C15	0.0602 (10)	0.0465 (8)	0.0329 (7)	−0.0064 (7)	0.0142 (7)	−0.0015 (6)
C16	0.0856 (14)	0.0472 (9)	0.0866 (14)	0.0010 (8)	0.0453 (11)	0.0004 (9)
C17	0.0818 (14)	0.0768 (13)	0.0902 (15)	0.0217 (10)	0.0466 (12)	0.0135 (11)
C18	0.0551 (10)	0.0856 (12)	0.0461 (10)	−0.0019 (9)	0.0198 (8)	0.0029 (8)
C19	0.0637 (11)	0.0619 (10)	0.0558 (10)	−0.0155 (8)	0.0188 (8)	−0.0026 (8)
C20	0.0582 (10)	0.0475 (8)	0.0505 (9)	−0.0055 (7)	0.0140 (7)	0.0030 (7)
N1	0.0465 (7)	0.0358 (6)	0.0405 (7)	0.0001 (5)	0.0020 (5)	−0.0033 (5)
N2	0.0433 (7)	0.0482 (7)	0.0384 (7)	−0.0094 (5)	0.0019 (5)	−0.0027 (5)
N3	0.0614 (12)	0.1421 (19)	0.0727 (12)	−0.0012 (13)	0.0299 (9)	0.0005 (12)
O1	0.0563 (7)	0.0400 (5)	0.0544 (7)	0.0028 (4)	−0.0028 (5)	−0.0017 (5)
O2	0.0836 (9)	0.0709 (7)	0.0413 (6)	−0.0298 (6)	0.0121 (6)	−0.0137 (5)
O3	0.0837 (12)	0.1591 (19)	0.183 (2)	−0.0499 (13)	0.0636 (13)	−0.0461 (16)
O4	0.0759 (11)	0.192 (2)	0.1528 (19)	0.0377 (13)	0.0546 (12)	0.0442 (16)

Geometric parameters (Å, º) top

C1—N1	1.4613 (17)	C10—C11	1.503 (3)
C1—C6	1.504 (2)	C10—H10A	0.97
C1—C2	1.519 (2)	C10—H10B	0.97
C1—H1	0.98	C11—C12	1.508 (4)
C2—C3	1.530 (2)	C11—H11A	0.97
C2—H2A	0.97	C11—H11B	0.97
C2—H2B	0.97	C12—C13	1.531 (3)
C3—C4	1.493 (3)	C12—H12A	0.97
C3—H3A	0.97	C12—H12B	0.97
C3—H3B	0.97	C13—H13A	0.97
C4—C5	1.510 (3)	C13—H13B	0.97
C4—H4A	0.97	C14—O2	1.2213 (17)
C4—H4B	0.97	C14—N2	1.365 (2)
C5—C6	1.521 (2)	C14—C15	1.494 (2)
C5—H5A	0.97	C15—C16	1.383 (2)
C5—H5B	0.97	C15—C20	1.385 (2)
C6—H6A	0.97	C16—C17	1.375 (3)
C6—H6B	0.97	C16—H16	0.93
C7—O1	1.2217 (16)	C17—C18	1.369 (3)
C7—N1	1.3213 (18)	C17—H17	0.93
C7—N2	1.4377 (17)	C18—C19	1.364 (3)
C8—N2	1.4834 (19)	C18—N3	1.477 (3)
C8—C13	1.512 (2)	C19—C20	1.381 (2)
C8—C9	1.515 (2)	C19—H19	0.93
C8—H8	0.98	C20—H20	0.93
C9—C10	1.526 (2)	N1—H1A	0.86
C9—H9A	0.97	N3—O3	1.200 (3)
C9—H9B	0.97	N3—O4	1.213 (3)

N1—C1—C6	110.17 (12)	C9—C10—H10A	109.4
N1—C1—C2	111.33 (12)	C11—C10—H10B	109.4
C6—C1—C2	110.94 (13)	C9—C10—H10B	109.4
N1—C1—H1	108.1	H10A—C10—H10B	108.0
C6—C1—H1	108.1	C10—C11—C12	111.1 (2)
C2—C1—H1	108.1	C10—C11—H11A	109.4
C1—C2—C3	110.45 (15)	C12—C11—H11A	109.4
C1—C2—H2A	109.6	C10—C11—H11B	109.4
C3—C2—H2A	109.6	C12—C11—H11B	109.4
C1—C2—H2B	109.6	H11A—C11—H11B	108.0
C3—C2—H2B	109.6	C11—C12—C13	110.85 (17)
H2A—C2—H2B	108.1	C11—C12—H12A	109.5
C4—C3—C2	111.43 (17)	C13—C12—H12A	109.5
C4—C3—H3A	109.3	C11—C12—H12B	109.5
C2—C3—H3A	109.3	C13—C12—H12B	109.5
C4—C3—H3B	109.3	H12A—C12—H12B	108.1
C2—C3—H3B	109.3	C8—C13—C12	110.96 (16)
H3A—C3—H3B	108.0	C8—C13—H13A	109.4
C3—C4—C5	110.71 (15)	C12—C13—H13A	109.4
C3—C4—H4A	109.5	C8—C13—H13B	109.4
C5—C4—H4A	109.5	C12—C13—H13B	109.4
C3—C4—H4B	109.5	H13A—C13—H13B	108.0
C5—C4—H4B	109.5	O2—C14—N2	122.40 (15)
H4A—C4—H4B	108.1	O2—C14—C15	119.65 (15)
C4—C5—C6	111.38 (16)	N2—C14—C15	117.92 (12)
C4—C5—H5A	109.4	C16—C15—C20	119.26 (16)
C6—C5—H5A	109.4	C16—C15—C14	119.19 (14)
C4—C5—H5B	109.4	C20—C15—C14	121.35 (14)
C6—C5—H5B	109.4	C17—C16—C15	120.97 (16)
H5A—C5—H5B	108.0	C17—C16—H16	119.5
C1—C6—C5	110.49 (14)	C15—C16—H16	119.5
C1—C6—H6A	109.6	C18—C17—C16	118.38 (17)
C5—C6—H6A	109.6	C18—C17—H17	120.8
C1—C6—H6B	109.6	C16—C17—H17	120.8
C5—C6—H6B	109.6	C19—C18—C17	122.23 (17)
H6A—C6—H6B	108.1	C19—C18—N3	118.54 (18)
O1—C7—N1	125.28 (13)	C17—C18—N3	119.23 (19)
O1—C7—N2	120.81 (12)	C18—C19—C20	119.19 (16)
N1—C7—N2	113.87 (12)	C18—C19—H19	120.4
N2—C8—C13	111.79 (13)	C20—C19—H19	120.4
N2—C8—C9	111.58 (12)	C19—C20—C15	119.96 (16)
C13—C8—C9	111.80 (16)	C19—C20—H20	120.0
N2—C8—H8	107.1	C15—C20—H20	120.0
C13—C8—H8	107.1	C7—N1—C1	123.38 (11)
C9—C8—H8	107.1	C7—N1—H1A	118.3
C8—C9—C10	110.73 (15)	C1—N1—H1A	118.3
C8—C9—H9A	109.5	C14—N2—C7	122.22 (12)
C10—C9—H9A	109.5	C14—N2—C8	120.06 (12)
C8—C9—H9B	109.5	C7—N2—C8	117.59 (12)
C10—C9—H9B	109.5	O3—N3—O4	124.0 (2)
H9A—C9—H9B	108.1	O3—N3—C18	118.4 (2)
C11—C10—C9	111.10 (17)	O4—N3—C18	117.5 (2)
C11—C10—H10A	109.4

N1—C1—C2—C3	179.16 (15)	C17—C18—C19—C20	0.3 (3)
C6—C1—C2—C3	56.1 (2)	N3—C18—C19—C20	−179.59 (16)
C1—C2—C3—C4	−56.0 (2)	C18—C19—C20—C15	−0.1 (3)
C2—C3—C4—C5	56.1 (2)	C16—C15—C20—C19	0.6 (2)
C3—C4—C5—C6	−56.5 (2)	C14—C15—C20—C19	175.33 (14)
N1—C1—C6—C5	179.75 (13)	O1—C7—N1—C1	4.9 (2)
C2—C1—C6—C5	−56.51 (19)	N2—C7—N1—C1	−177.33 (12)
C4—C5—C6—C1	56.7 (2)	C6—C1—N1—C7	−126.35 (15)
N2—C8—C9—C10	179.16 (15)	C2—C1—N1—C7	110.13 (16)
C13—C8—C9—C10	−54.8 (2)	O2—C14—N2—C7	−171.22 (13)
C8—C9—C10—C11	55.8 (2)	C15—C14—N2—C7	10.96 (19)
C9—C10—C11—C12	−57.2 (3)	O2—C14—N2—C8	4.6 (2)
C10—C11—C12—C13	56.8 (3)	C15—C14—N2—C8	−173.21 (12)
N2—C8—C13—C12	−179.41 (17)	O1—C7—N2—C14	−121.45 (16)
C9—C8—C13—C12	54.7 (2)	N1—C7—N2—C14	60.66 (18)
C11—C12—C13—C8	−55.3 (3)	O1—C7—N2—C8	62.63 (18)
O2—C14—C15—C16	53.2 (2)	N1—C7—N2—C8	−115.27 (14)
N2—C14—C15—C16	−128.91 (16)	C13—C8—N2—C14	97.56 (18)
O2—C14—C15—C20	−121.55 (17)	C9—C8—N2—C14	−136.42 (15)
N2—C14—C15—C20	56.33 (19)	C13—C8—N2—C7	−86.42 (17)
C20—C15—C16—C17	−1.3 (3)	C9—C8—N2—C7	39.60 (18)
C14—C15—C16—C17	−176.15 (17)	C19—C18—N3—O3	−0.8 (3)
C15—C16—C17—C18	1.5 (3)	C17—C18—N3—O3	179.3 (2)
C16—C17—C18—C19	−1.0 (3)	C19—C18—N3—O4	178.3 (2)
C16—C17—C18—N3	178.90 (17)	C17—C18—N3—O4	−1.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.10	2.9396 (15)	166
C1—H1···O2ⁱⁱ	0.98	2.43	3.3636 (18)	160

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₇N₃O₄
M_r	373.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	25.294 (2), 9.5757 (7), 16.6943 (14)
β (°)	105.140 (2)
V (Å³)	3903.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker 1999)
T_min, T_max	0.836, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	22623, 5012, 3152
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 1.02
No. of reflections	5012
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.10	2.9396 (15)	166
C1—H1···O2ⁱⁱ	0.98	2.43	3.3636 (18)	160

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

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, for providing data-collection facilities.

References

Amornraksa, K., Worachartcheewan, A. & Prachayasittikul, V. (2009). Eur. J. Sci. Res. 31, 510–518. Google Scholar
Bruker (1999). SADABS., Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 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 CSD CrossRef CAS IUCr Journals Google Scholar
Orea Flores, M. L., Galindo Guzmán, A., Gnecco Medina, D. & Bernès, S. (2006). Acta Cryst. E62, o2922–o2923. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, D.-Q., Wang, Y.-M., Du, N.-N., He, W.-Y., Chen, K.-L., Wang, G.-F., Yang, P., Wu, L.-Z., Zhang, X.-B. & Jiang, J.-D. (2009). Bioorg. Med. Chem. Lett. 19, 755–758. Web of Science CrossRef PubMed CAS Google Scholar
Song, D.-Q., Wang, Y., Wu, L.-J., Yang, P., Wang, Y.-M., Gao, L.-M., Li, Y., Qu, J.-R., Wang, Y.-H., Li, Y.-H., Du, N.-N., Han, Y.-X., Zhang, Z.-P. & Jiang, J.-D. (2008). J. Med. Chem. 51, 3094–3103. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-W. & Peng, Y. (2008). Acta Cryst. E64, o160. Web of Science CSD CrossRef IUCr Journals Google Scholar