r-2,c-6-Bis(4-methoxy­phenyl)-c-3,t-3-dimethyl-1-nitro­sopiperidin-4-one

Kavitha, T.; Ponnuswamy, S.; Sakthivel, P.; Karthik, K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809019357

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1420

doi:10.1107/S1600536809019357

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r-2,c-6-Bis(4-methoxyphenyl)-c-3,t-3-dimethyl-1-nitrosopiperidin-4-one

T. Kavitha,^a S. Ponnuswamy,^b P. Sakthivel,^b K. Karthik ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, Tamil Nadu, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 15 May 2009; accepted 21 May 2009; online 29 May 2009)

In the title compound, C₂₁H₂₄N₂O₄, the piperidine ring adopts a distorted boat conformation. The crystal structure is stabilized by C—H⋯π interactions involving one of the methoxyphenyl rings.

Related literature

For the biological activity of piperidones, see: Dimmock et al. (1990 ); Mutus et al. (1989 ); Perumal et al. (2001 ). For ring conformations, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₄
M_r = 368.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.2540 (3) Å
b = 15.0469 (6) Å
c = 17.0741 (7) Å
V = 1863.64 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.973, T_max = 0.982
24656 measured reflections
3211 independent reflections
2595 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.03
3211 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯Cg1ⁱ	0.96	2.97	3.9108 (26)	167
C23—H23C⋯Cg1ⁱⁱ	0.96	2.86	3.7201 (27)	149
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019357/ci2805sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019357/ci2805Isup2.hkl

checkCIF report

Comment top

2,6-Disubstituted 4-piperidones are found to have various biological and pharmacological activities (Dimmock et al., 1990; Mutus et al., 1989). Piperidones are also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001).

The piperidine ring adopts a distorted boat conformation, with puckering parameters (Cremer & Pople, 1975) q2 = 0.613 (2) Å, q3 = -0.123 (2) Å and ϕ2 = 260.6 (2)° and the asymmetry parameters ΔC_s(C2) = ΔC_s(C5) = 21.7 (2)° (Nardelli, 1983). The C8—C13 and C16—C21 phenyl rings are oriented at angles of 88.04 (6)° and 82.38 (7)°, respectively, with the best plane (N1/C3/C4/C6) through the piperidine ring. The C14 methyl group is oriented axially [N1—C2—C3—C14 = 53.8 (2)°] while the C15 methyl group is oriented equatorially [N1—C2—C3—C15 = 173.3 (2)°] to the piperidinone ring. The sum of bond angles around N1 [358.1°] shows that the atom N1 is in sp² hybridzed state. There is a delocalization between the lone pair of electrons and the hetero π-electrons of the nitroso group.

The packing of the molecules in the crystal is through C—H··· π interactions.

Related literature top

For the biological activity of piperidones, see: Dimmock et al. (1990); Mutus et al. (1989); Perumal et al. (2001). For ring conformations, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To a solution of r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one (1.69 g, 5 mmol) in chloroform (10 ml) was added with conc. HCl (1.5 ml) and water (1.5 ml) and while stirring, solid NaNO₂ (0.84 g,12 mmol) was added in portions over the period of 0.5 h. The solution was stirred at room temperature for another 0.5 h. The organic layer was washed with water, saturated with aqueous NaHCO₃ and dried over anhydrous Na₂SO₄. The resulting solution was concentrated and the residue was crystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1983).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Part of the crystal packing of the title compound, viewed approximately along the a axis. Dashed lines indicate C—H···π interactions. H atoms not involved in the interactions have been omitted.

r-2,c-6-Bis(4-methoxyphenyl)-c-3,t-3-dimethyl-1-nitrosopiperidin-4-one top

Crystal data top

C₂₁H₂₄N₂O₄	F(000) = 784
M_r = 368.42	D_x = 1.313 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3211 reflections
a = 7.2540 (3) Å	θ = 2.4–30.5°
b = 15.0469 (6) Å	µ = 0.09 mm⁻¹
c = 17.0741 (7) Å	T = 293 K
V = 1863.64 (13) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa-APEXII CCD area-detector diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	2595 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 30.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.973, T_max = 0.982	k = −21→21
24656 measured reflections	l = −24→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0532P)² + 0.2754P] where P = (F_o² + 2F_c²)/3
3211 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₄	V = 1863.64 (13) Å³
M_r = 368.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.2540 (3) Å	µ = 0.09 mm⁻¹
b = 15.0469 (6) Å	T = 293 K
c = 17.0741 (7) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa-APEXII CCD area-detector diffractometer	3211 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2595 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.026
24656 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3211 reflections	Δρ_min = −0.15 e Å⁻³
244 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
N1	0.0483 (2)	0.52808 (12)	0.21105 (9)	0.0433 (4)
C2	0.1305 (2)	0.58054 (13)	0.27489 (10)	0.0417 (4)
H2	0.0276	0.6015	0.3072	0.050*
C3	0.2206 (3)	0.66398 (14)	0.23982 (11)	0.0453 (4)
C4	0.3709 (3)	0.63719 (14)	0.18259 (11)	0.0478 (4)
C5	0.3450 (3)	0.54846 (14)	0.14164 (11)	0.0464 (4)
H5A	0.4235	0.5054	0.1675	0.056*
H5B	0.3898	0.5547	0.0884	0.056*
C6	0.1494 (3)	0.50917 (13)	0.13767 (10)	0.0419 (4)
H6	0.0840	0.5392	0.0950	0.050*
N7	−0.1331 (2)	0.51769 (14)	0.21570 (12)	0.0589 (5)
C8	0.2461 (3)	0.52025 (13)	0.32719 (10)	0.0413 (4)
C9	0.4369 (3)	0.51945 (15)	0.33242 (11)	0.0461 (4)
H9	0.5048	0.5589	0.3020	0.055*
C10	0.5290 (3)	0.46138 (15)	0.38177 (12)	0.0500 (5)
H10	0.6571	0.4620	0.3837	0.060*
C11	0.4317 (3)	0.40259 (13)	0.42807 (12)	0.0484 (4)
C12	0.2405 (3)	0.40122 (16)	0.42284 (13)	0.0562 (5)
H12	0.1730	0.3611	0.4528	0.067*
C13	0.1513 (3)	0.45897 (15)	0.37357 (12)	0.0517 (5)
H13	0.0233	0.4573	0.3710	0.062*
C15	0.2886 (4)	0.72672 (16)	0.30428 (13)	0.0581 (5)
H15A	0.3445	0.7781	0.2809	0.087*
H15B	0.3777	0.6965	0.3362	0.087*
H15C	0.1863	0.7449	0.3361	0.087*
C14	0.0774 (3)	0.71461 (16)	0.18933 (14)	0.0578 (5)
H14A	0.1337	0.7666	0.1673	0.087*
H14B	−0.0251	0.7319	0.2215	0.087*
H14C	0.0347	0.6767	0.1479	0.087*
C16	0.1535 (2)	0.41093 (12)	0.11881 (10)	0.0393 (4)
C17	0.2309 (3)	0.34891 (14)	0.16965 (10)	0.0449 (4)
H17	0.2793	0.3677	0.2173	0.054*
C18	0.2366 (3)	0.26016 (14)	0.15030 (11)	0.0443 (4)
H18	0.2889	0.2195	0.1848	0.053*
C19	0.1647 (2)	0.23100 (12)	0.07945 (10)	0.0402 (4)
C20	0.0887 (3)	0.29189 (13)	0.02797 (11)	0.0430 (4)
H20	0.0414	0.2731	−0.0199	0.052*
C21	0.0838 (3)	0.38045 (14)	0.04814 (10)	0.0431 (4)
H21	0.0322	0.4210	0.0134	0.052*
C22	0.7010 (4)	0.34767 (19)	0.49303 (17)	0.0719 (7)
H22A	0.7349	0.3045	0.5318	0.108*
H22B	0.7358	0.4059	0.5107	0.108*
H22C	0.7632	0.3346	0.4448	0.108*
C23	0.1004 (4)	0.10995 (15)	−0.00595 (14)	0.0605 (6)
H23A	0.1152	0.0466	−0.0089	0.091*
H23B	0.1638	0.1374	−0.0490	0.091*
H23C	−0.0283	0.1245	−0.0085	0.091*
O1	0.5033 (3)	0.68301 (12)	0.16938 (12)	0.0732 (5)
O2	−0.2050 (2)	0.48520 (14)	0.15739 (11)	0.0753 (5)
O3	0.5071 (3)	0.34479 (11)	0.48087 (10)	0.0640 (4)
O4	0.1751 (2)	0.14144 (9)	0.06582 (8)	0.0509 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0311 (6)	0.0576 (9)	0.0412 (7)	0.0002 (7)	0.0008 (6)	−0.0093 (7)
C2	0.0358 (8)	0.0543 (10)	0.0348 (8)	−0.0009 (8)	0.0034 (7)	−0.0084 (7)
C3	0.0446 (9)	0.0519 (10)	0.0393 (8)	0.0004 (8)	0.0037 (8)	−0.0051 (8)
C4	0.0461 (10)	0.0531 (11)	0.0442 (9)	−0.0003 (9)	0.0077 (8)	0.0035 (8)
C5	0.0432 (9)	0.0573 (11)	0.0387 (8)	0.0012 (9)	0.0088 (8)	−0.0034 (8)
C6	0.0403 (8)	0.0522 (10)	0.0331 (8)	0.0041 (8)	−0.0015 (7)	−0.0029 (7)
N7	0.0347 (8)	0.0767 (12)	0.0654 (11)	−0.0027 (8)	−0.0038 (8)	−0.0179 (10)
C8	0.0390 (8)	0.0525 (11)	0.0323 (7)	−0.0055 (8)	0.0015 (7)	−0.0049 (8)
C9	0.0401 (9)	0.0592 (11)	0.0389 (9)	−0.0079 (9)	0.0024 (7)	0.0025 (9)
C10	0.0432 (9)	0.0621 (12)	0.0449 (10)	−0.0046 (9)	−0.0008 (9)	−0.0002 (9)
C11	0.0600 (12)	0.0453 (10)	0.0400 (9)	−0.0028 (9)	0.0003 (9)	−0.0036 (8)
C12	0.0600 (12)	0.0569 (12)	0.0516 (11)	−0.0158 (10)	0.0075 (10)	0.0059 (10)
C13	0.0410 (9)	0.0638 (13)	0.0504 (10)	−0.0121 (10)	0.0056 (9)	0.0009 (10)
C15	0.0579 (12)	0.0581 (12)	0.0582 (12)	−0.0077 (10)	0.0029 (11)	−0.0143 (10)
C14	0.0607 (13)	0.0600 (12)	0.0527 (11)	0.0116 (11)	−0.0001 (11)	−0.0026 (10)
C16	0.0356 (8)	0.0494 (9)	0.0329 (7)	0.0046 (8)	−0.0010 (7)	−0.0024 (7)
C17	0.0425 (9)	0.0604 (11)	0.0319 (8)	0.0043 (9)	−0.0063 (7)	−0.0014 (8)
C18	0.0390 (9)	0.0555 (11)	0.0383 (8)	0.0070 (8)	−0.0033 (7)	0.0074 (8)
C19	0.0324 (8)	0.0480 (9)	0.0403 (8)	0.0009 (7)	0.0050 (7)	0.0008 (7)
C20	0.0420 (9)	0.0533 (10)	0.0336 (8)	0.0022 (8)	−0.0047 (7)	−0.0021 (8)
C21	0.0432 (9)	0.0523 (10)	0.0337 (8)	0.0060 (8)	−0.0065 (7)	0.0020 (8)
C22	0.0729 (16)	0.0707 (16)	0.0723 (15)	0.0205 (14)	−0.0010 (14)	0.0133 (13)
C23	0.0649 (13)	0.0527 (12)	0.0638 (13)	−0.0002 (11)	−0.0052 (12)	−0.0134 (11)
O1	0.0684 (10)	0.0652 (10)	0.0858 (13)	−0.0185 (9)	0.0299 (10)	−0.0047 (9)
O2	0.0420 (8)	0.1026 (14)	0.0812 (11)	0.0025 (9)	−0.0132 (8)	−0.0327 (11)
O3	0.0740 (11)	0.0592 (9)	0.0589 (9)	−0.0050 (9)	−0.0057 (9)	0.0118 (8)
O4	0.0543 (8)	0.0467 (7)	0.0516 (7)	0.0036 (6)	−0.0011 (7)	0.0001 (6)

Geometric parameters (Å, º) top

N1—N7	1.328 (2)	C13—H13	0.93
N1—C2	1.472 (2)	C15—H15A	0.96
N1—C6	1.479 (2)	C15—H15B	0.96
C2—C8	1.524 (3)	C15—H15C	0.96
C2—C3	1.537 (3)	C14—H14A	0.96
C2—H2	0.98	C14—H14B	0.96
C3—C4	1.519 (3)	C14—H14C	0.96
C3—C15	1.532 (3)	C16—C21	1.386 (2)
C3—C14	1.550 (3)	C16—C17	1.393 (3)
C4—O1	1.204 (2)	C17—C18	1.376 (3)
C4—C5	1.519 (3)	C17—H17	0.93
C5—C6	1.539 (3)	C18—C19	1.389 (3)
C5—H5A	0.97	C18—H18	0.93
C5—H5B	0.97	C19—O4	1.370 (2)
C6—C16	1.513 (3)	C19—C20	1.384 (3)
C6—H6	0.98	C20—C21	1.377 (3)
N7—O2	1.225 (2)	C20—H20	0.93
C8—C9	1.387 (3)	C21—H21	0.93
C8—C13	1.396 (3)	C22—O3	1.423 (3)
C9—C10	1.385 (3)	C22—H22A	0.96
C9—H9	0.93	C22—H22B	0.96
C10—C11	1.380 (3)	C22—H22C	0.96
C10—H10	0.93	C23—O4	1.421 (3)
C11—O3	1.367 (3)	C23—H23A	0.96
C11—C12	1.390 (3)	C23—H23B	0.96
C12—C13	1.372 (3)	C23—H23C	0.96
C12—H12	0.93

N7—N1—C2	114.87 (16)	C12—C13—H13	118.9
N7—N1—C6	121.28 (17)	C8—C13—H13	118.9
C2—N1—C6	121.97 (14)	C3—C15—H15A	109.5
N1—C2—C8	109.72 (15)	C3—C15—H15B	109.5
N1—C2—C3	108.78 (15)	H15A—C15—H15B	109.5
C8—C2—C3	118.74 (16)	C3—C15—H15C	109.5
N1—C2—H2	106.3	H15A—C15—H15C	109.5
C8—C2—H2	106.3	H15B—C15—H15C	109.5
C3—C2—H2	106.3	C3—C14—H14A	109.5
C4—C3—C15	113.24 (18)	C3—C14—H14B	109.5
C4—C3—C2	109.81 (16)	H14A—C14—H14B	109.5
C15—C3—C2	111.14 (16)	C3—C14—H14C	109.5
C4—C3—C14	104.71 (16)	H14A—C14—H14C	109.5
C15—C3—C14	108.22 (18)	H14B—C14—H14C	109.5
C2—C3—C14	109.47 (17)	C21—C16—C17	117.90 (17)
O1—C4—C5	121.09 (19)	C21—C16—C6	120.07 (16)
O1—C4—C3	122.78 (19)	C17—C16—C6	122.00 (16)
C5—C4—C3	116.13 (17)	C18—C17—C16	120.84 (17)
C4—C5—C6	118.19 (17)	C18—C17—H17	119.6
C4—C5—H5A	107.8	C16—C17—H17	119.6
C6—C5—H5A	107.8	C17—C18—C19	120.29 (18)
C4—C5—H5B	107.8	C17—C18—H18	119.9
C6—C5—H5B	107.8	C19—C18—H18	119.9
H5A—C5—H5B	107.1	O4—C19—C20	124.43 (17)
N1—C6—C16	112.22 (16)	O4—C19—C18	115.98 (17)
N1—C6—C5	110.23 (15)	C20—C19—C18	119.58 (18)
C16—C6—C5	111.48 (16)	C21—C20—C19	119.48 (17)
N1—C6—H6	107.6	C21—C20—H20	120.3
C16—C6—H6	107.6	C19—C20—H20	120.3
C5—C6—H6	107.6	C20—C21—C16	121.90 (17)
O2—N7—N1	114.82 (19)	C20—C21—H21	119.1
C9—C8—C13	116.69 (19)	C16—C21—H21	119.1
C9—C8—C2	126.27 (18)	O3—C22—H22A	109.5
C13—C8—C2	117.03 (17)	O3—C22—H22B	109.5
C10—C9—C8	121.70 (19)	H22A—C22—H22B	109.5
C10—C9—H9	119.2	O3—C22—H22C	109.5
C8—C9—H9	119.2	H22A—C22—H22C	109.5
C11—C10—C9	120.41 (19)	H22B—C22—H22C	109.5
C11—C10—H10	119.8	O4—C23—H23A	109.5
C9—C10—H10	119.8	O4—C23—H23B	109.5
O3—C11—C10	125.5 (2)	H23A—C23—H23B	109.5
O3—C11—C12	115.6 (2)	O4—C23—H23C	109.5
C10—C11—C12	118.9 (2)	H23A—C23—H23C	109.5
C13—C12—C11	120.0 (2)	H23B—C23—H23C	109.5
C13—C12—H12	120.0	C11—O3—C22	118.20 (19)
C11—C12—H12	120.0	C19—O4—C23	116.96 (16)
C12—C13—C8	122.26 (19)

N7—N1—C2—C8	110.4 (2)	C3—C2—C8—C13	164.11 (17)
C6—N1—C2—C8	−85.0 (2)	C13—C8—C9—C10	−0.6 (3)
N7—N1—C2—C3	−118.2 (2)	C2—C8—C9—C10	−179.66 (17)
C6—N1—C2—C3	46.4 (2)	C8—C9—C10—C11	−0.6 (3)
N1—C2—C3—C4	−60.6 (2)	C9—C10—C11—O3	−177.43 (19)
C8—C2—C3—C4	65.7 (2)	C9—C10—C11—C12	1.6 (3)
N1—C2—C3—C15	173.29 (16)	O3—C11—C12—C13	177.69 (18)
C8—C2—C3—C15	−60.3 (2)	C10—C11—C12—C13	−1.4 (3)
N1—C2—C3—C14	53.80 (19)	C11—C12—C13—C8	0.2 (3)
C8—C2—C3—C14	−179.83 (16)	C9—C8—C13—C12	0.8 (3)
C15—C3—C4—O1	−26.9 (3)	C2—C8—C13—C12	179.92 (19)
C2—C3—C4—O1	−151.7 (2)	N1—C6—C16—C21	122.51 (18)
C14—C3—C4—O1	90.8 (3)	C5—C6—C16—C21	−113.29 (19)
C15—C3—C4—C5	153.57 (19)	N1—C6—C16—C17	−59.4 (2)
C2—C3—C4—C5	28.7 (2)	C5—C6—C16—C17	64.8 (2)
C14—C3—C4—C5	−88.7 (2)	C21—C16—C17—C18	−0.4 (3)
O1—C4—C5—C6	−158.8 (2)	C6—C16—C17—C18	−178.54 (18)
C3—C4—C5—C6	20.8 (3)	C16—C17—C18—C19	−0.1 (3)
N7—N1—C6—C16	−69.4 (2)	C17—C18—C19—O4	−179.38 (18)
C2—N1—C6—C16	127.05 (19)	C17—C18—C19—C20	0.6 (3)
N7—N1—C6—C5	165.7 (2)	O4—C19—C20—C21	179.33 (18)
C2—N1—C6—C5	2.1 (2)	C18—C19—C20—C21	−0.7 (3)
C4—C5—C6—N1	−37.0 (2)	C19—C20—C21—C16	0.2 (3)
C4—C5—C6—C16	−162.27 (16)	C17—C16—C21—C20	0.3 (3)
C2—N1—N7—O2	170.12 (19)	C6—C16—C21—C20	178.52 (18)
C6—N1—N7—O2	5.4 (3)	C10—C11—O3—C22	3.6 (3)
N1—C2—C8—C9	109.0 (2)	C12—C11—O3—C22	−175.5 (2)
C3—C2—C8—C9	−16.9 (3)	C20—C19—O4—C23	−0.7 (3)
N1—C2—C8—C13	−70.0 (2)	C18—C19—O4—C23	179.28 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Cg1ⁱ	0.96	2.97	3.911 (3)	167
C23—H23C···Cg1ⁱⁱ	0.96	2.86	3.720 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₄
M_r	368.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.2540 (3), 15.0469 (6), 17.0741 (7)
V (Å³)	1863.64 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa-APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	24656, 3211, 2595
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.03
No. of reflections	3211
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1983).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Cg1ⁱ	0.96	2.97	3.9108 (26)	167
C23—H23C···Cg1ⁱⁱ	0.96	2.86	3.7201 (27)	149

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

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection. SP thanks the UGC, India, for financial support.

References

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