9-(2,4-Dinitro­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

Sureshbabu, N.; Sughanya, V.

doi:10.1107/S1600536813001384

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o281

doi:10.1107/S1600536813001384

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9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

N. Sureshbabu ^a and V. Sughanya ^a ^*

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
^*Correspondence e-mail: saisukanyashri@gmail.com

(Received 6 January 2013; accepted 14 January 2013; online 23 January 2013)

In the title compound, C₂₃H₂₄N₂O₇, the central 4H-pyran ring adopts a flattened boat conformation, whereas both cyclohexenone rings adopt envelope conformations, the C atom bearing the dimethyl substituent being the flap atom in each case. The mean and maximum deviation of the pyran ring are 0.0379 (4) and 0.0605 (3) Å. The mean plane of the pyran ring and the dinitrobenzene ring make a dihedral angle of 85.88 (2)°.

Related literature

For the synthesis of xanthenes, see: Vanag & Stankevich (1960 ); Hilderbrand & Weissleder (2007 ). For their pharmaceutical properties, see: Dimmock et al. (1988 ); Lambert et al. (1997 ); Poupelin et al. (1978 ); Hideo (1981 ); Selvanayagam et al. (1996 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Odabaşoğlu et al. (2008 ); Reddy et al. (2009 ); Mehdi et al. (2011 ); Sughanya & Sureshbabu (2012 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₂₄N₂O₇
M_r = 440.44
Monoclinic, P 2₁ /c
a = 9.7733 (3) Å
b = 19.6193 (5) Å
c = 11.7922 (3) Å
β = 109.603 (1)°
V = 2130.04 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.905, T_max = 0.975
29785 measured reflections
7327 independent reflections
4793 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.03
7327 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813001384/im2418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001384/im2418Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001384/im2418Isup3.cml

checkCIF report

Comment top

Xanthene is the parent compound of a number of naturally occurring substances and some synthetic dyes. Xanthene derivatives are used as dyes (Hilderbrand & Weissleder, 2007), possess biological properties like antibacterial, antiviral and anti-inflammatory (Dimmock et al., 1988) activities and are used in medicine. Ehretianone, a quinonoid xanthene was reported to possess antisnake venom activity (Selvanayagam et al., 1996; Lambert et al., 1997; Poupelin et al., 1978; Hideo, 1981).

The central pyran B (O1/C1/C6/C7/C8/C13) ring almost planar with a mean deviation from the mean plane of 0.0379 (4) Å and a maximum deviation of 0.061 (3) Å for C7. O1 and C7 are moved out of this mean plane towards the direction which means that the ring may also be described as a highly flattened boat conformation. The rings A (C8—C13), B (O1/C1/C6/C7/C8/C13) and C (C1—C6) show total puckering amplitudes Q(T) of 0.4602 (15) Å, 0.0988 (2) Å, 0.4479 (16) Å, respectively. The cyclohexenone rings A and C both adopt envelope conformations, whereas the central B ring adopts a flattened boat conformation. This can be rationalized by the respective puckering parameters (Cremer & Pople, 1975) ϕ = 177.6 (2)° and θ = 53.65 (2)° for A, ϕ = 179.0 (8)° and θ = 84.7 (2)° for B, ϕ = -54.5 (12)° and θ = 126.82 (2)° for C, respectively. The planar phenyl substituent and the central pyran ring form a dihedral angle of 85.88 (2)°. In the title compound, bond lengths (Allen et al., 1987) and angles are generally within normal ranges. In the pyran ring C1—C6 and C8—C13 are double bonds in nature (C1—C6 1.333 (8) Å and C8—C13 1.334 (2) Å), as indicated by the bond distances. The C1—C6—C5 (118.81 (12)°) and C13—C8—C9 (118.70 (2)°) angles are almost identical. In this conformation C3 and C11 must be described as flap atoms being situated out of the plane of the ring with deviations of 0.316 (2) Å and 0.325 (2) Å, respectively. The observed carbonyl bond lengths C5—O2 = 1.223 (2) Å and C9—O3 = 1.216 (2) Å are also normal.

Related literature top

For the synthesis of xanthenes, see: Vanag & Stankevich (1960); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Dimmock et al. (1988); Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996). For bond-length data, see: Allen et al. (1987). For related structures, see: Odabaşoğlu et al. (2008); Reddy et al. (2009); Mehdi et al. (2011); Sughanya & Sureshbabu (2012). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

Following a literature method (Vanag & Stankevich, 1960) a mixture of 2,4-dinitrobenzaldehyde (0.588 g, 3 m mol) and 5,5-dimethylcyclohexane-1,3-dione (0.84 g, 6 m mol) was dissolved in 25 ml of ethanol in a 100 ml round bottomed flask. To this solution about 15 drops of concentrated hydrochloric acid were added and the content was refluxed for 30 minutes. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and stirred well. The formed precipitate was filtered and dried. The yellow crystal used for data collection was obtained by crystallization from ethanol at room temperature,(m.p.446 K, yield: 86%).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the structure of title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione top

Crystal data top

C₂₃H₂₄N₂O₇	F(000) = 928
M_r = 440.44	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 446 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7733 (3) Å	Cell parameters from 8512 reflections
b = 19.6193 (5) Å	θ = 2.2–31.1°
c = 11.7922 (3) Å	µ = 0.10 mm⁻¹
β = 109.603 (1)°	T = 296 K
V = 2130.04 (10) Å³	Block, yellow
Z = 4	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	7327 independent reflections
Radiation source: fine-focus sealed tube	4793 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scan	θ_max = 32.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.905, T_max = 0.975	k = −29→27
29785 measured reflections	l = −15→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0777P)² + 0.3517P] where P = (F_o² + 2F_c²)/3
7327 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₂₄N₂O₇	V = 2130.04 (10) Å³
M_r = 440.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7733 (3) Å	µ = 0.10 mm⁻¹
b = 19.6193 (5) Å	T = 296 K
c = 11.7922 (3) Å	0.35 × 0.30 × 0.25 mm
β = 109.603 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	7327 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4793 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.975	R_int = 0.031
29785 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
7327 reflections	Δρ_min = −0.30 e Å⁻³
289 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
C1	0.51973 (13)	0.15131 (7)	0.58305 (11)	0.0339 (3)
C2	0.41933 (15)	0.19984 (8)	0.61245 (13)	0.0434 (3)
H2A	0.4760	0.2353	0.6648	0.052*
H2B	0.3659	0.1758	0.6561	0.052*
C3	0.31152 (14)	0.23285 (8)	0.50052 (13)	0.0397 (3)
C4	0.24534 (14)	0.17645 (8)	0.40933 (14)	0.0432 (3)
H4A	0.1827	0.1488	0.4393	0.052*
H4B	0.1851	0.1973	0.3347	0.052*
C5	0.35407 (13)	0.13059 (7)	0.38268 (12)	0.0372 (3)
C6	0.49306 (12)	0.11891 (7)	0.47847 (11)	0.0325 (3)
C7	0.59949 (13)	0.06997 (6)	0.45403 (10)	0.0303 (2)
H7	0.5504	0.0265	0.4260	0.036*
C8	0.72373 (13)	0.05827 (6)	0.56996 (11)	0.0309 (2)
C9	0.83150 (13)	0.00583 (7)	0.57141 (11)	0.0338 (3)
C10	0.95370 (15)	−0.00702 (7)	0.68746 (12)	0.0393 (3)
H10A	1.0378	−0.0227	0.6687	0.047*
H10B	0.9251	−0.0433	0.7308	0.047*
C11	0.99723 (14)	0.05519 (7)	0.76956 (12)	0.0383 (3)
C12	0.85972 (15)	0.08387 (8)	0.78692 (11)	0.0406 (3)
H12A	0.8279	0.0530	0.8374	0.049*
H12B	0.8822	0.1274	0.8281	0.049*
C13	0.73989 (13)	0.09328 (7)	0.67058 (11)	0.0330 (3)
C14	0.38929 (18)	0.28478 (9)	0.44734 (16)	0.0541 (4)
H14A	0.4308	0.3198	0.5056	0.081*
H14B	0.3210	0.3048	0.3766	0.081*
H14C	0.4649	0.2624	0.4264	0.081*
C15	0.19240 (17)	0.26822 (10)	0.53505 (17)	0.0551 (4)
H15A	0.2344	0.3036	0.5925	0.083*
H15B	0.1449	0.2356	0.5699	0.083*
H15C	0.1228	0.2878	0.4645	0.083*
C16	1.10517 (18)	0.03431 (10)	0.89168 (14)	0.0594 (5)
H16A	1.0614	0.0007	0.9279	0.089*
H16B	1.1313	0.0736	0.9431	0.089*
H16C	1.1906	0.0155	0.8808	0.089*
C17	1.06762 (17)	0.10848 (9)	0.71315 (15)	0.0509 (4)
H17A	1.0003	0.1220	0.6365	0.076*
H17B	1.1530	0.0896	0.7023	0.076*
H17C	1.0940	0.1475	0.7651	0.076*
C18	0.65475 (12)	0.09886 (6)	0.35707 (10)	0.0295 (2)
C19	0.61732 (13)	0.07634 (7)	0.23872 (11)	0.0313 (2)
C20	0.66867 (14)	0.10639 (7)	0.15506 (11)	0.0361 (3)
H20	0.6414	0.0904	0.0764	0.043*
C21	0.76167 (14)	0.16090 (7)	0.19241 (12)	0.0379 (3)
C22	0.80053 (16)	0.18654 (8)	0.30670 (13)	0.0425 (3)
H22	0.8618	0.2241	0.3294	0.051*
C23	0.74630 (15)	0.15511 (7)	0.38759 (12)	0.0382 (3)
H23	0.7721	0.1723	0.4655	0.046*
N1	0.51735 (13)	0.01863 (7)	0.19194 (10)	0.0422 (3)
N2	0.81838 (16)	0.19342 (8)	0.10531 (13)	0.0543 (4)
O1	0.64491 (10)	0.14292 (5)	0.67914 (8)	0.0384 (2)
O2	0.32732 (11)	0.10217 (6)	0.28536 (9)	0.0516 (3)
O3	0.81924 (12)	−0.02696 (6)	0.48107 (9)	0.0491 (3)
O4	0.52780 (15)	−0.03162 (6)	0.25373 (11)	0.0642 (4)
O5	0.42986 (15)	0.02476 (8)	0.09097 (11)	0.0723 (4)
O6	0.7810 (2)	0.17153 (9)	0.00386 (14)	0.0984 (6)
O7	0.89653 (17)	0.24275 (8)	0.13837 (14)	0.0805 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0318 (5)	0.0406 (7)	0.0304 (6)	0.0049 (5)	0.0120 (5)	0.0037 (5)
C2	0.0425 (7)	0.0530 (9)	0.0372 (7)	0.0145 (6)	0.0168 (6)	0.0015 (6)
C3	0.0347 (6)	0.0417 (8)	0.0427 (7)	0.0055 (5)	0.0131 (5)	0.0038 (6)
C4	0.0306 (6)	0.0467 (8)	0.0494 (8)	0.0011 (5)	0.0095 (5)	0.0013 (6)
C5	0.0308 (6)	0.0426 (7)	0.0377 (7)	−0.0029 (5)	0.0109 (5)	0.0018 (5)
C6	0.0295 (5)	0.0382 (7)	0.0311 (6)	0.0010 (5)	0.0119 (4)	0.0029 (5)
C7	0.0317 (5)	0.0334 (6)	0.0268 (5)	−0.0018 (5)	0.0109 (4)	−0.0004 (4)
C8	0.0317 (5)	0.0343 (6)	0.0279 (5)	0.0012 (5)	0.0116 (4)	0.0014 (5)
C9	0.0354 (6)	0.0329 (6)	0.0343 (6)	−0.0005 (5)	0.0133 (5)	−0.0013 (5)
C10	0.0377 (6)	0.0379 (7)	0.0400 (7)	0.0065 (5)	0.0099 (5)	−0.0002 (6)
C11	0.0346 (6)	0.0439 (8)	0.0331 (6)	0.0061 (5)	0.0069 (5)	−0.0041 (5)
C12	0.0403 (6)	0.0539 (9)	0.0263 (6)	0.0099 (6)	0.0094 (5)	−0.0011 (5)
C13	0.0328 (5)	0.0394 (7)	0.0283 (6)	0.0063 (5)	0.0125 (4)	0.0025 (5)
C14	0.0495 (8)	0.0476 (9)	0.0650 (10)	−0.0020 (7)	0.0189 (7)	0.0097 (8)
C15	0.0455 (8)	0.0576 (10)	0.0643 (10)	0.0162 (7)	0.0212 (7)	0.0023 (8)
C16	0.0495 (8)	0.0747 (12)	0.0417 (8)	0.0207 (8)	−0.0010 (7)	−0.0062 (8)
C17	0.0452 (8)	0.0524 (9)	0.0559 (9)	−0.0092 (7)	0.0180 (7)	−0.0133 (7)
C18	0.0309 (5)	0.0316 (6)	0.0270 (5)	0.0013 (4)	0.0108 (4)	0.0006 (4)
C19	0.0321 (5)	0.0334 (6)	0.0281 (6)	0.0002 (5)	0.0098 (4)	−0.0014 (5)
C20	0.0403 (6)	0.0426 (7)	0.0272 (6)	0.0066 (5)	0.0137 (5)	0.0023 (5)
C21	0.0406 (6)	0.0399 (7)	0.0399 (7)	0.0055 (5)	0.0222 (5)	0.0101 (5)
C22	0.0452 (7)	0.0382 (7)	0.0463 (8)	−0.0086 (6)	0.0183 (6)	0.0017 (6)
C23	0.0444 (7)	0.0381 (7)	0.0328 (6)	−0.0073 (6)	0.0138 (5)	−0.0034 (5)
N1	0.0436 (6)	0.0483 (7)	0.0337 (6)	−0.0087 (5)	0.0115 (5)	−0.0092 (5)
N2	0.0629 (8)	0.0574 (9)	0.0552 (8)	0.0032 (7)	0.0367 (7)	0.0144 (7)
O1	0.0376 (5)	0.0481 (6)	0.0284 (4)	0.0115 (4)	0.0096 (4)	−0.0031 (4)
O2	0.0387 (5)	0.0704 (8)	0.0398 (6)	0.0021 (5)	0.0052 (4)	−0.0092 (5)
O3	0.0528 (6)	0.0513 (6)	0.0419 (6)	0.0084 (5)	0.0141 (5)	−0.0121 (5)
O4	0.0859 (9)	0.0470 (7)	0.0540 (7)	−0.0244 (6)	0.0157 (6)	−0.0048 (5)
O5	0.0660 (8)	0.0897 (10)	0.0424 (6)	−0.0206 (7)	−0.0067 (6)	−0.0088 (6)
O6	0.1521 (16)	0.1066 (13)	0.0657 (9)	−0.0304 (11)	0.0749 (11)	−0.0055 (9)
O7	0.0924 (10)	0.0799 (10)	0.0826 (10)	−0.0268 (8)	0.0471 (8)	0.0168 (8)

Geometric parameters (Å, º) top

C1—C6	1.3331 (18)	C12—H12B	0.9700
C1—O1	1.3702 (15)	C13—O1	1.3723 (15)
C1—C2	1.4892 (18)	C14—H14A	0.9600
C2—C3	1.5293 (19)	C14—H14B	0.9600
C2—H2A	0.9700	C14—H14C	0.9600
C2—H2B	0.9700	C15—H15A	0.9600
C3—C15	1.523 (2)	C15—H15B	0.9600
C3—C14	1.526 (2)	C15—H15C	0.9600
C3—C4	1.527 (2)	C16—H16A	0.9600
C4—C5	1.504 (2)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700	C17—H17A	0.9600
C5—O2	1.2226 (17)	C17—H17B	0.9600
C5—C6	1.4643 (17)	C17—H17C	0.9600
C6—C7	1.5127 (17)	C18—C23	1.3899 (18)
C7—C8	1.5107 (16)	C18—C19	1.3908 (16)
C7—C18	1.5279 (17)	C19—C20	1.3801 (18)
C7—H7	0.9800	C19—N1	1.4762 (17)
C8—C13	1.3338 (17)	C20—C21	1.377 (2)
C8—C9	1.4683 (17)	C20—H20	0.9300
C9—O3	1.2155 (15)	C21—C22	1.368 (2)
C9—C10	1.5054 (18)	C21—N2	1.4667 (18)
C10—C11	1.5270 (19)	C22—C23	1.3820 (19)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—H23	0.9300
C11—C17	1.522 (2)	N1—O4	1.2096 (17)
C11—C16	1.5280 (19)	N1—O5	1.2166 (16)
C11—C12	1.5327 (18)	N2—O6	1.207 (2)
C12—C13	1.4864 (17)	N2—O7	1.213 (2)
C12—H12A	0.9700

C6—C1—O1	123.43 (11)	C11—C12—H12B	109.2
C6—C1—C2	125.49 (11)	H12A—C12—H12B	107.9
O1—C1—C2	111.07 (11)	C8—C13—O1	123.36 (11)
C1—C2—C3	112.76 (11)	C8—C13—C12	125.35 (11)
C1—C2—H2A	109.0	O1—C13—C12	111.29 (11)
C3—C2—H2A	109.0	C3—C14—H14A	109.5
C1—C2—H2B	109.0	C3—C14—H14B	109.5
C3—C2—H2B	109.0	H14A—C14—H14B	109.5
H2A—C2—H2B	107.8	C3—C14—H14C	109.5
C15—C3—C14	109.66 (13)	H14A—C14—H14C	109.5
C15—C3—C4	109.71 (12)	H14B—C14—H14C	109.5
C14—C3—C4	110.24 (13)	C3—C15—H15A	109.5
C15—C3—C2	109.23 (12)	C3—C15—H15B	109.5
C14—C3—C2	110.09 (12)	H15A—C15—H15B	109.5
C4—C3—C2	107.89 (12)	C3—C15—H15C	109.5
C5—C4—C3	114.75 (11)	H15A—C15—H15C	109.5
C5—C4—H4A	108.6	H15B—C15—H15C	109.5
C3—C4—H4A	108.6	C11—C16—H16A	109.5
C5—C4—H4B	108.6	C11—C16—H16B	109.5
C3—C4—H4B	108.6	H16A—C16—H16B	109.5
H4A—C4—H4B	107.6	C11—C16—H16C	109.5
O2—C5—C6	120.23 (12)	H16A—C16—H16C	109.5
O2—C5—C4	121.70 (12)	H16B—C16—H16C	109.5
C6—C5—C4	118.04 (12)	C11—C17—H17A	109.5
C1—C6—C5	118.81 (12)	C11—C17—H17B	109.5
C1—C6—C7	123.05 (11)	H17A—C17—H17B	109.5
C5—C6—C7	118.14 (11)	C11—C17—H17C	109.5
C8—C7—C6	108.62 (10)	H17A—C17—H17C	109.5
C8—C7—C18	110.80 (10)	H17B—C17—H17C	109.5
C6—C7—C18	110.21 (10)	C23—C18—C19	116.22 (11)
C8—C7—H7	109.1	C23—C18—C7	117.34 (11)
C6—C7—H7	109.1	C19—C18—C7	126.38 (11)
C18—C7—H7	109.1	C20—C19—C18	123.04 (12)
C13—C8—C9	118.70 (11)	C20—C19—N1	114.48 (11)
C13—C8—C7	123.10 (11)	C18—C19—N1	122.48 (11)
C9—C8—C7	118.21 (11)	C21—C20—C19	117.55 (12)
O3—C9—C8	120.08 (12)	C21—C20—H20	121.2
O3—C9—C10	121.53 (12)	C19—C20—H20	121.2
C8—C9—C10	118.37 (11)	C22—C21—C20	122.43 (12)
C9—C10—C11	114.19 (11)	C22—C21—N2	119.00 (13)
C9—C10—H10A	108.7	C20—C21—N2	118.56 (13)
C11—C10—H10A	108.7	C21—C22—C23	118.17 (13)
C9—C10—H10B	108.7	C21—C22—H22	120.9
C11—C10—H10B	108.7	C23—C22—H22	120.9
H10A—C10—H10B	107.6	C22—C23—C18	122.56 (12)
C17—C11—C10	110.04 (12)	C22—C23—H23	118.7
C17—C11—C16	109.01 (13)	C18—C23—H23	118.7
C10—C11—C16	109.91 (12)	O4—N1—O5	124.03 (13)
C17—C11—C12	110.57 (12)	O4—N1—C19	119.24 (11)
C10—C11—C12	107.93 (11)	O5—N1—C19	116.72 (13)
C16—C11—C12	109.37 (11)	O6—N2—O7	123.44 (15)
C13—C12—C11	112.15 (11)	O6—N2—C21	118.66 (15)
C13—C12—H12A	109.2	O7—N2—C21	117.84 (15)
C11—C12—H12A	109.2	C1—O1—C13	117.56 (10)
C13—C12—H12B	109.2

C6—C1—C2—C3	−24.1 (2)	C16—C11—C12—C13	−169.45 (14)
O1—C1—C2—C3	156.81 (12)	C9—C8—C13—O1	−179.49 (11)
C1—C2—C3—C15	166.99 (13)	C7—C8—C13—O1	0.5 (2)
C1—C2—C3—C14	−72.55 (17)	C9—C8—C13—C12	−0.1 (2)
C1—C2—C3—C4	47.79 (16)	C7—C8—C13—C12	179.97 (12)
C15—C3—C4—C5	−170.89 (13)	C11—C12—C13—C8	26.1 (2)
C14—C3—C4—C5	68.26 (16)	C11—C12—C13—O1	−154.43 (12)
C2—C3—C4—C5	−51.99 (16)	C8—C7—C18—C23	−50.45 (15)
C3—C4—C5—O2	−151.35 (14)	C6—C7—C18—C23	69.81 (14)
C3—C4—C5—C6	30.51 (18)	C8—C7—C18—C19	132.67 (13)
O1—C1—C6—C5	178.65 (12)	C6—C7—C18—C19	−107.07 (14)
C2—C1—C6—C5	−0.3 (2)	C23—C18—C19—C20	1.15 (19)
O1—C1—C6—C7	−0.9 (2)	C7—C18—C19—C20	178.06 (12)
C2—C1—C6—C7	−179.87 (13)	C23—C18—C19—N1	−178.00 (12)
O2—C5—C6—C1	179.17 (13)	C7—C18—C19—N1	−1.09 (19)
C4—C5—C6—C1	−2.66 (19)	C18—C19—C20—C21	0.32 (19)
O2—C5—C6—C7	−1.26 (19)	N1—C19—C20—C21	179.54 (11)
C4—C5—C6—C7	176.91 (12)	C19—C20—C21—C22	−1.7 (2)
C1—C6—C7—C8	7.67 (17)	C19—C20—C21—N2	179.64 (12)
C5—C6—C7—C8	−171.88 (11)	C20—C21—C22—C23	1.5 (2)
C1—C6—C7—C18	−113.88 (13)	N2—C21—C22—C23	−179.84 (13)
C5—C6—C7—C18	66.57 (14)	C21—C22—C23—C18	0.1 (2)
C6—C7—C8—C13	−7.50 (17)	C19—C18—C23—C22	−1.4 (2)
C18—C7—C8—C13	113.70 (13)	C7—C18—C23—C22	−178.56 (13)
C6—C7—C8—C9	172.53 (11)	C20—C19—N1—O4	138.94 (14)
C18—C7—C8—C9	−66.27 (14)	C18—C19—N1—O4	−41.84 (19)
C13—C8—C9—O3	179.81 (13)	C20—C19—N1—O5	−39.93 (18)
C7—C8—C9—O3	−0.22 (19)	C18—C19—N1—O5	139.28 (14)
C13—C8—C9—C10	1.31 (18)	C22—C21—N2—O6	−178.31 (17)
C7—C8—C9—C10	−178.72 (11)	C20—C21—N2—O6	0.4 (2)
O3—C9—C10—C11	152.40 (13)	C22—C21—N2—O7	−1.0 (2)
C8—C9—C10—C11	−29.12 (17)	C20—C21—N2—O7	177.70 (15)
C9—C10—C11—C17	−68.38 (15)	C6—C1—O1—C13	−7.06 (19)
C9—C10—C11—C16	171.56 (12)	C2—C1—O1—C13	172.05 (12)
C9—C10—C11—C12	52.36 (16)	C8—C13—O1—C1	7.24 (19)
C17—C11—C12—C13	70.50 (16)	C12—C13—O1—C1	−172.26 (11)
C10—C11—C12—C13	−49.90 (16)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄N₂O₇
M_r	440.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.7733 (3), 19.6193 (5), 11.7922 (3)
β (°)	109.603 (1)
V (Å³)	2130.04 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.905, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	29785, 7327, 4793
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.745

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.159, 1.03
No. of reflections	7327
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008).

Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT Madras, for the data collection.

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