2-Meth­oxy-1-(2-meth­oxy-4-nitro­naphthalen-1-yl)-6-nitro­naphthalene

Wannalerse, B.; Pannil, W.; Loriang, J.; Tuntulani, T.; Duangthongyou, T.

doi:10.1107/S1600536813008660

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o682

https://doi.org/10.1107/S1600536813008660

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2-Methoxy-1-(2-methoxy-4-nitronaphthalen-1-yl)-6-nitronaphthalene

Boontana Wannalerse,^a ^* Wilasinee Pannil,^a Jaruwan Loriang,^a Thawatchai Tuntulani ^b and Tanwawan Duangthongyou ^c ^*

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, ^bSupramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand, and ^cDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand
^*Correspondence e-mail: , fscitwd@ku.ac.th

(Received 18 February 2013; accepted 29 March 2013; online 10 April 2013)

In the title compound, C₂₂H₁₆N₂O₆, the naphthalene ring systems form a dihedral angle of 65.2 (1)°. Two O atoms of one of the nitro groups are disordered over two sets of sites with occupancy factors of 0.586 (15) and 0.414 (15). Weak C—H⋯O intermolecular interactions are present, forming a ladder like structure along the a axis.

Related literature

For related structures, see: Thorup et al. (2006 ,) ; Thoss et al. (2009 ); Ge & Li (2009 ).

Experimental

Crystal data

C₂₂H₁₆N₂O₆
M_r = 404.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.095 (16) Å
b = 15.14 (4) Å
c = 17.86 (5) Å
V = 1918 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.36 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
3043 measured reflections
1881 independent reflections
1440 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.01
1881 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.93	2.59	3.361 (10)	140
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813008660/lr2099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008660/lr2099Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008660/lr2099Isup3.cml

checkCIF report

Comment top

The molecule of the title compound, C₂₂H₁₆N₂O₆, contains two naphthalene rings forming a dihedral angle of 65.2 (1)° between them. The molecular structure is shown in Fig.1. The crystal structure is stabilized by weak C17—H17···O2 intermolecular interactions forming a ladder like structure, along the a axis (Fig. 2).

Related literature top

For related structures, see: Thorup et al. (2006, ); Thoss et al. (2009); Ge & Li (2009).

Experimental top

The (S)-2,2'-dimethoxy-1,1'-binaphthalene (0.5 g,1.98 mmol) was stirred in CH₃CN(10 ml). Nitric acid (0.4 ml) in glacial acetic acid (5 ml) was added dropwise in 10 minutes. The mixture was then stirred at 70°C for 16 h after pouring into the water (50 ml) and extracted with dichloromethane (3x50 ml). The organic layer was washed with 1M KOH, brine and dried over Na₂SO₄. The mixture was filtrated and evaporated of the solvent afforded a yellow solid,then purified by column chromatography using dichloromethane: hexane = 7:3 as an eluent. Brown crystal were obtained from a mixture of dichloromethane:hexane.

Structure description top

For related structures, see: Thorup et al. (2006, ); Thoss et al. (2009); Ge & Li (2009).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing view of the compound (dash lines represent weak C—H···O interaction).

2-Methoxy-1-(2-methoxy-4-nitronaphthalen-1-yl)-6-nitronaphthalene top

Crystal data top

C₂₂H₁₆N₂O₆	F(000) = 840
M_r = 404.37	D_x = 1.400 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1608 reflections
a = 7.095 (16) Å	θ = 2.7–18.9°
b = 15.14 (4) Å	µ = 0.10 mm⁻¹
c = 17.86 (5) Å	T = 296 K
V = 1918 (9) Å³	Bar, brown
Z = 4	0.36 × 0.16 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	1440 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 24.8°, θ_min = 2.9°
φ and ω scans	h = −6→8
3043 measured reflections	k = 0→17
1881 independent reflections	l = 0→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0534P)² + 0.0581P] where P = (F_o² + 2F_c²)/3
1881 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O₆	V = 1918 (9) Å³
M_r = 404.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.095 (16) Å	µ = 0.10 mm⁻¹
b = 15.14 (4) Å	T = 296 K
c = 17.86 (5) Å	0.36 × 0.16 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	1440 reflections with I > 2σ(I)
3043 measured reflections	R_int = 0.023
1881 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	Δρ_max = 0.10 e Å⁻³
1881 reflections	Δρ_min = −0.16 e Å⁻³
292 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 > 2sigma(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	Occ. (<1)
O1	0.1345 (6)	0.40153 (18)	0.28224 (16)	0.1209 (13)
O2	0.1746 (4)	0.46589 (15)	0.38886 (16)	0.0921 (8)
O3	0.2362 (3)	−0.03073 (11)	0.59542 (10)	0.0567 (6)
O6	0.5329 (3)	0.02923 (12)	0.40128 (11)	0.0520 (5)
N1	0.1607 (4)	0.39888 (18)	0.35029 (19)	0.0688 (8)
N2	0.3170 (5)	−0.25427 (17)	0.30186 (17)	0.0626 (7)
C1	0.1670 (4)	0.31102 (18)	0.38691 (17)	0.0480 (7)
C2	0.1735 (4)	0.23483 (18)	0.34021 (16)	0.0515 (7)
H2	0.1702	0.2405	0.2884	0.062*
C3	0.1849 (4)	0.15274 (19)	0.37294 (15)	0.0484 (7)
H3	0.1889	0.1028	0.3426	0.058*
C4	0.1908 (4)	0.14237 (16)	0.45239 (15)	0.0393 (6)
C5	0.2108 (4)	0.05732 (16)	0.48721 (14)	0.0405 (6)
C6	0.2104 (4)	0.05224 (16)	0.56536 (14)	0.0437 (7)
C7	0.1857 (4)	0.12987 (18)	0.61018 (16)	0.0496 (7)
H7	0.1817	0.1252	0.6621	0.059*
C8	0.1679 (4)	0.21108 (18)	0.57691 (15)	0.0478 (7)
H8	0.1519	0.2608	0.6068	0.057*
C9	0.1735 (4)	0.22098 (16)	0.49791 (15)	0.0411 (7)
C10	0.1630 (4)	0.30550 (17)	0.46272 (17)	0.0474 (7)
H10	0.1534	0.3564	0.4916	0.057*
C11	0.2143 (6)	−0.0425 (2)	0.67474 (16)	0.0815 (11)
H11A	0.0950	−0.0188	0.6902	0.122*
H11B	0.3140	−0.0122	0.7005	0.122*
H11C	0.2192	−0.1043	0.6865	0.122*
C12	0.2779 (4)	−0.17661 (17)	0.35106 (14)	0.0447 (7)
C13	0.1069 (4)	−0.17088 (17)	0.39423 (15)	0.0442 (7)
C14	−0.0412 (4)	−0.23552 (19)	0.39645 (17)	0.0565 (8)
H14	−0.0313	−0.2861	0.3672	0.068*
C15	−0.1982 (5)	−0.2240 (2)	0.44130 (18)	0.0622 (9)
H15	−0.2907	−0.2675	0.4428	0.075*
C16	−0.2194 (5)	−0.1468 (2)	0.48479 (17)	0.0606 (8)
H16	−0.3267	−0.1390	0.5140	0.073*
C17	−0.0808 (4)	−0.08277 (19)	0.48406 (15)	0.0493 (7)
H17	−0.0969	−0.0322	0.5129	0.059*
C18	0.0887 (4)	−0.09202 (16)	0.43966 (15)	0.0410 (6)
C19	0.2341 (4)	−0.02545 (16)	0.44096 (13)	0.0396 (6)
C20	0.3965 (4)	−0.03611 (16)	0.39655 (15)	0.0414 (6)
C21	0.4176 (4)	−0.11250 (16)	0.35163 (15)	0.0445 (7)
H21	0.5252	−0.1197	0.3225	0.053*
C22	0.6813 (4)	0.0311 (2)	0.34571 (16)	0.0582 (8)
H22A	0.6268	0.0373	0.2968	0.087*
H22B	0.7521	−0.0228	0.3481	0.087*
H22C	0.7634	0.0802	0.3554	0.087*
O4A	0.448 (2)	−0.2544 (8)	0.2597 (5)	0.093 (3)	0.586 (15)
O5A	0.1822 (7)	−0.2895 (6)	0.2681 (5)	0.099 (4)	0.586 (15)
O4B	0.479 (2)	−0.2756 (12)	0.2933 (11)	0.098 (5)	0.414 (15)
O5B	0.250 (2)	−0.3295 (4)	0.3232 (8)	0.114 (6)	0.414 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.222 (4)	0.0738 (17)	0.0670 (17)	0.010 (2)	0.024 (2)	0.0264 (15)
O2	0.118 (2)	0.0473 (14)	0.111 (2)	−0.0124 (14)	−0.0229 (18)	0.0075 (15)
O3	0.0807 (14)	0.0467 (11)	0.0425 (10)	0.0087 (11)	0.0065 (11)	0.0015 (10)
O6	0.0450 (10)	0.0511 (11)	0.0599 (12)	−0.0070 (9)	0.0132 (10)	−0.0137 (11)
N1	0.0765 (19)	0.0542 (17)	0.076 (2)	−0.0037 (15)	0.0094 (17)	0.0106 (17)
N2	0.078 (2)	0.0498 (17)	0.0600 (19)	0.0029 (17)	−0.0004 (18)	−0.0139 (15)
C1	0.0424 (15)	0.0427 (15)	0.059 (2)	0.0005 (14)	0.0053 (14)	0.0083 (14)
C2	0.0532 (17)	0.0575 (18)	0.0437 (17)	0.0017 (16)	0.0024 (14)	0.0016 (16)
C3	0.0540 (18)	0.0464 (16)	0.0449 (16)	0.0049 (16)	0.0043 (15)	−0.0033 (13)
C4	0.0341 (14)	0.0427 (15)	0.0411 (15)	0.0013 (13)	0.0030 (12)	−0.0026 (13)
C5	0.0412 (15)	0.0388 (14)	0.0414 (14)	0.0023 (13)	0.0053 (12)	−0.0060 (12)
C6	0.0462 (16)	0.0440 (15)	0.0409 (15)	0.0012 (14)	0.0035 (13)	−0.0002 (13)
C7	0.0568 (17)	0.0544 (18)	0.0375 (16)	0.0021 (15)	0.0052 (15)	−0.0068 (14)
C8	0.0513 (16)	0.0459 (16)	0.0462 (17)	0.0036 (14)	0.0055 (14)	−0.0123 (14)
C9	0.0368 (14)	0.0408 (14)	0.0457 (16)	0.0006 (14)	0.0026 (12)	−0.0035 (13)
C10	0.0407 (15)	0.0413 (15)	0.0601 (19)	0.0005 (13)	0.0069 (14)	−0.0085 (15)
C11	0.136 (3)	0.0622 (19)	0.0467 (18)	0.007 (2)	0.020 (2)	0.0107 (16)
C12	0.0596 (18)	0.0376 (14)	0.0368 (14)	0.0100 (15)	−0.0055 (14)	−0.0056 (13)
C13	0.0510 (16)	0.0395 (14)	0.0420 (16)	0.0047 (14)	−0.0071 (13)	0.0053 (14)
C14	0.069 (2)	0.0482 (16)	0.053 (2)	−0.0082 (16)	−0.0136 (17)	0.0005 (16)
C15	0.063 (2)	0.0585 (19)	0.065 (2)	−0.0234 (18)	−0.0104 (18)	0.0144 (17)
C16	0.0518 (19)	0.072 (2)	0.0583 (19)	−0.0074 (18)	0.0034 (16)	0.0146 (18)
C17	0.0500 (16)	0.0501 (15)	0.0479 (17)	0.0034 (16)	0.0036 (14)	0.0059 (15)
C18	0.0470 (15)	0.0383 (14)	0.0376 (14)	0.0025 (14)	−0.0040 (13)	0.0072 (13)
C19	0.0446 (15)	0.0393 (14)	0.0349 (14)	0.0036 (13)	0.0002 (13)	0.0014 (12)
C20	0.0461 (15)	0.0379 (14)	0.0403 (15)	0.0036 (13)	−0.0008 (13)	−0.0042 (14)
C21	0.0471 (16)	0.0456 (15)	0.0408 (16)	0.0078 (14)	0.0020 (13)	−0.0045 (14)
C22	0.0557 (18)	0.0656 (19)	0.0532 (17)	−0.0046 (17)	0.0131 (16)	−0.0008 (17)
O4A	0.132 (9)	0.072 (5)	0.075 (5)	−0.014 (5)	0.053 (6)	−0.031 (4)
O5A	0.085 (3)	0.096 (6)	0.117 (7)	−0.003 (3)	−0.020 (3)	−0.061 (5)
O4B	0.073 (5)	0.095 (10)	0.125 (13)	0.021 (6)	0.005 (8)	−0.052 (9)
O5B	0.194 (12)	0.035 (4)	0.112 (9)	−0.022 (5)	0.071 (9)	−0.015 (4)

Geometric parameters (Å, º) top

O1—N1	1.230 (5)	C8—H8	0.9300
O2—N1	1.230 (4)	C9—C10	1.428 (5)
O3—C6	1.378 (4)	C10—H10	0.9300
O3—C11	1.436 (5)	C11—H11A	0.9600
O6—C20	1.386 (4)	C11—H11B	0.9600
O6—C22	1.447 (4)	C11—H11C	0.9600
N1—C1	1.483 (5)	C12—C21	1.387 (5)
N2—O4A	1.193 (12)	C12—C13	1.440 (5)
N2—O4B	1.206 (17)	C13—C14	1.436 (5)
N2—O5A	1.250 (5)	C13—C18	1.449 (5)
N2—O5B	1.292 (7)	C14—C15	1.383 (5)
N2—C12	1.494 (4)	C14—H14	0.9300
C1—C10	1.357 (5)	C15—C16	1.412 (5)
C1—C2	1.424 (5)	C15—H15	0.9300
C2—C3	1.376 (5)	C16—C17	1.381 (5)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.428 (5)	C17—C18	1.448 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.437 (5)	C18—C19	1.442 (4)
C4—C9	1.447 (5)	C19—C20	1.408 (4)
C5—C6	1.398 (5)	C20—C21	1.416 (4)
C5—C19	1.510 (5)	C21—H21	0.9300
C6—C7	1.433 (5)	C22—H22A	0.9600
C7—C8	1.371 (5)	C22—H22B	0.9600
C7—H7	0.9300	C22—H22C	0.9600
C8—C9	1.419 (5)

C6—O3—C11	118.9 (2)	C9—C10—H10	120.2
C20—O6—C22	118.7 (2)	O3—C11—H11A	109.5
O1—N1—O2	122.6 (3)	O3—C11—H11B	109.5
O1—N1—C1	118.0 (3)	H11A—C11—H11B	109.5
O2—N1—C1	119.4 (3)	O3—C11—H11C	109.5
O4A—N2—O4B	34.8 (7)	H11A—C11—H11C	109.5
O4A—N2—O5A	106.8 (8)	H11B—C11—H11C	109.5
O4B—N2—O5A	123.8 (9)	C21—C12—C13	123.8 (3)
O4A—N2—O5B	118.1 (8)	C21—C12—N2	115.0 (3)
O4B—N2—O5B	98.9 (13)	C13—C12—N2	121.3 (3)
O5A—N2—O5B	58.9 (5)	C14—C13—C12	126.2 (3)
O4A—N2—C12	121.1 (6)	C14—C13—C18	118.7 (3)
O4B—N2—C12	117.6 (8)	C12—C13—C18	115.1 (2)
O5A—N2—C12	118.5 (4)	C15—C14—C13	121.3 (3)
O5B—N2—C12	116.9 (4)	C15—C14—H14	119.4
C10—C1—C2	122.4 (3)	C13—C14—H14	119.4
C10—C1—N1	119.6 (3)	C14—C15—C16	120.6 (3)
C2—C1—N1	118.0 (3)	C14—C15—H15	119.7
C3—C2—C1	119.0 (3)	C16—C15—H15	119.7
C3—C2—H2	120.5	C17—C16—C15	120.0 (3)
C1—C2—H2	120.5	C17—C16—H16	120.0
C2—C3—C4	121.6 (3)	C15—C16—H16	120.0
C2—C3—H3	119.2	C16—C17—C18	121.9 (3)
C4—C3—H3	119.2	C16—C17—H17	119.0
C3—C4—C5	122.1 (2)	C18—C17—H17	119.0
C3—C4—C9	117.7 (3)	C19—C18—C17	121.2 (3)
C5—C4—C9	120.2 (3)	C19—C18—C13	121.4 (3)
C6—C5—C4	118.8 (2)	C17—C18—C13	117.4 (2)
C6—C5—C19	120.0 (2)	C20—C19—C18	119.7 (3)
C4—C5—C19	121.2 (3)	C20—C19—C5	119.5 (2)
O3—C6—C5	116.0 (2)	C18—C19—C5	120.7 (2)
O3—C6—C7	123.1 (3)	O6—C20—C19	117.1 (2)
C5—C6—C7	120.9 (3)	O6—C20—C21	122.9 (3)
C8—C7—C6	120.3 (3)	C19—C20—C21	120.0 (2)
C8—C7—H7	119.8	C12—C21—C20	120.0 (3)
C6—C7—H7	119.8	C12—C21—H21	120.0
C7—C8—C9	121.5 (2)	C20—C21—H21	120.0
C7—C8—H8	119.2	O6—C22—H22A	109.5
C9—C8—H8	119.2	O6—C22—H22B	109.5
C8—C9—C10	122.1 (2)	H22A—C22—H22B	109.5
C8—C9—C4	118.3 (3)	O6—C22—H22C	109.5
C10—C9—C4	119.6 (3)	H22A—C22—H22C	109.5
C1—C10—C9	119.6 (3)	H22B—C22—H22C	109.5
C1—C10—H10	120.2

O1—N1—C1—C10	−168.7 (3)	O4B—N2—C12—C13	−148.8 (11)
O2—N1—C1—C10	8.6 (5)	O5A—N2—C12—C13	36.0 (7)
O1—N1—C1—C2	10.1 (5)	O5B—N2—C12—C13	−31.5 (11)
O2—N1—C1—C2	−172.6 (3)	C21—C12—C13—C14	−179.3 (3)
C10—C1—C2—C3	−3.1 (4)	N2—C12—C13—C14	0.5 (4)
N1—C1—C2—C3	178.2 (3)	C21—C12—C13—C18	0.0 (4)
C1—C2—C3—C4	−0.2 (4)	N2—C12—C13—C18	179.7 (2)
C2—C3—C4—C5	−177.3 (3)	C12—C13—C14—C15	178.6 (3)
C2—C3—C4—C9	3.5 (4)	C18—C13—C14—C15	−0.6 (4)
C3—C4—C5—C6	−178.3 (3)	C13—C14—C15—C16	1.7 (4)
C9—C4—C5—C6	0.9 (4)	C14—C15—C16—C17	−1.4 (5)
C3—C4—C5—C19	2.3 (4)	C15—C16—C17—C18	−0.1 (4)
C9—C4—C5—C19	−178.4 (2)	C16—C17—C18—C19	−178.5 (3)
C11—O3—C6—C5	−172.4 (3)	C16—C17—C18—C13	1.2 (4)
C11—O3—C6—C7	8.0 (4)	C14—C13—C18—C19	178.8 (2)
C4—C5—C6—O3	−178.0 (2)	C12—C13—C18—C19	−0.5 (3)
C19—C5—C6—O3	1.4 (4)	C14—C13—C18—C17	−0.9 (3)
C4—C5—C6—C7	1.6 (4)	C12—C13—C18—C17	179.8 (2)
C19—C5—C6—C7	−179.1 (2)	C17—C18—C19—C20	−179.4 (2)
O3—C6—C7—C8	177.5 (3)	C13—C18—C19—C20	0.9 (4)
C5—C6—C7—C8	−2.1 (4)	C17—C18—C19—C5	−1.8 (4)
C6—C7—C8—C9	0.0 (5)	C13—C18—C19—C5	178.6 (2)
C7—C8—C9—C10	−177.4 (3)	C6—C5—C19—C20	−114.4 (3)
C7—C8—C9—C4	2.5 (4)	C4—C5—C19—C20	64.9 (3)
C3—C4—C9—C8	176.4 (2)	C6—C5—C19—C18	68.0 (3)
C5—C4—C9—C8	−2.9 (4)	C4—C5—C19—C18	−112.7 (3)
C3—C4—C9—C10	−3.8 (4)	C22—O6—C20—C19	−166.9 (2)
C5—C4—C9—C10	176.9 (3)	C22—O6—C20—C21	15.2 (4)
C2—C1—C10—C9	2.7 (5)	C18—C19—C20—O6	−178.8 (2)
N1—C1—C10—C9	−178.5 (2)	C5—C19—C20—O6	3.5 (3)
C8—C9—C10—C1	−179.3 (3)	C18—C19—C20—C21	−0.8 (4)
C4—C9—C10—C1	0.8 (4)	C5—C19—C20—C21	−178.5 (2)
O4A—N2—C12—C21	−9.0 (9)	C13—C12—C21—C20	0.1 (4)
O4B—N2—C12—C21	30.9 (12)	N2—C12—C21—C20	−179.6 (2)
O5A—N2—C12—C21	−144.3 (7)	O6—C20—C21—C12	178.2 (2)
O5B—N2—C12—C21	148.3 (10)	C19—C20—C21—C12	0.3 (4)
O4A—N2—C12—C13	171.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.59	3.361 (10)	140

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₆
M_r	404.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.095 (16), 15.14 (4), 17.86 (5)
V (Å³)	1918 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3043, 1881, 1440
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.589

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.01
No. of reflections	1881
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.16

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.59	3.361 (10)	140

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

The authors thank the Thailand Research Fund (MRG 580182), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Education, Ministry of Education, Kasetsart University Research and Development Institute (5410127000) and the Department of Chemistry, Faculty of Science, Kasetsart University for financial support.

References

Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ge, J.-Z. & Li, H. (2009). Acta Cryst. E65, o1179. 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
Thorup, N., Deussen, H.-J., Bechgaard, K. & Bjørnholm, T. (2006). Acta Cryst. E62, o1342–o1343. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Thoss, M., Seidel, R. W. & Feigel, M. (2009). Acta Cryst. E65, o243. Web of Science CSD CrossRef IUCr Journals Google Scholar