N-(4-Meth­oxy-2-nitro­phen­yl)-N-(methyl­sulfon­yl)methane­sulfonamide

Yousuf, S.; Siddiqui, H.; Farooq, R.; Choudhary, M.I.

doi:10.1107/S160053681202483X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2090

https://doi.org/10.1107/S160053681202483X

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N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

Sammer Yousuf,^a ^* Hina Siddiqui,^a Rabia Farooq ^a and M. Iqbal Choudhary ^a,^b

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Biochemistry, Faculty of Sciences, King Abdul Aziz University, Jeddah 21589, Saudi Arabia
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 29 May 2012; accepted 31 May 2012; online 13 June 2012)

In the title compound, C₉H₁₂N₂O₇S₂, the nitro substituent is slightly twisted from the benzene ring [dihedral angle = 14.69 (10)°]. The molecular geometry is stabilized by intramolecular C—H⋯O hydrogen bonds, forming S(6) ring motifs. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into layers parallel to (10-2).

Related literature

For the biological activities of sulfonamides, see: Alsughayer et al. (2011 ); Joshi & Khosla (2003 ); Scozzafava et al. (2003 ); Drews (2000 ); Peixoto & Beverley (1987 ). For crystal structures of closely related compounds, see: Boechat et al. (2010 ); Zia-ur-Rehman et al. (2009 ).

Experimental

Crystal data

C₉H₁₂N₂O₇S₂
M_r = 324.33
Monoclinic, P 2₁ /c
a = 9.4976 (7) Å
b = 7.5987 (6) Å
c = 19.2434 (15) Å
β = 103.672 (2)°
V = 1349.43 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 273 K
0.55 × 0.47 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.799, T_max = 0.955
9504 measured reflections
3362 independent reflections
2711 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.05
3362 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2ⁱ	0.93	2.46	3.368 (2)	165
C8—H8B⋯O4	0.96	2.58	3.225 (3)	125
C8—H8C⋯O5ⁱⁱ	0.96	2.58	3.250 (3)	127
C9—H9B⋯O1	0.96	2.59	3.226 (3)	124
C9—H9B⋯O1ⁱⁱⁱ	0.96	2.47	3.173 (3)	130
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202483X/is5148sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202483X/is5148Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202483X/is5148Isup3.cml

checkCIF report

Comment top

Compounds containing the sulfonamide moiety have attracted a wide interest due to their interesting chemical and biological properties, which makes them promising candidates in drug discovery. Sulfonamides posses wide variety of biological activities including anti-bacterial, anti-leishmanial, anti-inflammatory, anti-cancer, and carbonic anhydrase inhibitory activities (Alsughayer et al., 2011; Joshi & Khosla, 2003; Scozzafava et al., 2003; Drews, 2000; Peixoto & Beverley, 1987). The title compound was prepared as a part of our ongoing research to synthesize different sulfonamide derivatives to study their bioactive potential and structure activity relationship (SAR). In the title compound (Fig. 1), the nitro group was found to be slightly twisted with the dihedral angle of 14.69 (10)° between the NO₂ group and the benzene ring. The S1—N2—C3—C4 and S2—N2—C3—C4 torsion angles are 82.83 (19) and -92.42 (17)°, respectively. The molecule is stabilized by two intramolecular C8—H8B···O4 and C9—H9B···O1 interactions to form two S(6) ring motifs. In the crystal structure, the molecules are linked to form a two-dimensional network through C1—H1B···O2ⁱ, C8—H8C···O5ⁱⁱ and C9—H9B···O1ⁱⁱⁱ intermolecular hydrogen bonds (Fig. 2 and Table 1). The bond lengths and angles are within the normal range and similar to other closley related structures (Boechat et al., 2010; Zia-ur-Rehman et al., 2009).

Related literature top

For the biological activities of sulfonamides, see: Alsughayer et al. (2011); Joshi & Khosla (2003); Scozzafava et al. (2003); Drews (2000); Peixoto & Beverley (1987). For crystal structures of closely related compounds, see: Boechat et al. (2010); Zia-ur-Rehman et al. (2009).

Experimental top

To a stirring solution of methanesulfonyl chloride (1.0 g, 8.7 mmol) in CH₂Cl₂ (20 ml) at 0 °C, 3 ml Et₃N and 4-methoxy-2-nitroaniline (1.1 eq., 1.61 g m, 9.6 mmol) were added along with catalytic amount of dimethylamino pyridine (DMAP). Progress of the reaction was monitored by thin layer chromatography in 7:3 hexanes: ethyl acetate solvent system. After complete consumption of starting material (2 hrs), workup was performed with H₂O (10 ml), organic layer was separated and aqueous layer was extracted with CH₂Cl₂ (2 × 10 ml). Organic layers were further washed with brine (10 ml), and dried over MgSO₄, filtered, and concentrated in vacuum to obtain the crude product (0.9 g, 90% yield). Flash chromatography was performed hexanes: ethyl acetate (7:3), to obtain crystalline compound I, in 55% yield. Crystals were found suitable for single-crystal X-ray diffraction studies. All the starting materials and solvents were purchased from commercial suppliers and used for reaction without purification.

Structure description top

For the biological activities of sulfonamides, see: Alsughayer et al. (2011); Joshi & Khosla (2003); Scozzafava et al. (2003); Drews (2000); Peixoto & Beverley (1987). For crystal structures of closely related compounds, see: Boechat et al. (2010); Zia-ur-Rehman et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the title compound. Only hydrogen atoms involved in hydrogen bonding are shown.

N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide top

Crystal data top

C₉H₁₂N₂O₇S₂	F(000) = 672
M_r = 324.33	D_x = 1.596 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3096 reflections
a = 9.4976 (7) Å	θ = 2.2–27.7°
b = 7.5987 (6) Å	µ = 0.43 mm⁻¹
c = 19.2434 (15) Å	T = 273 K
β = 103.672 (2)°	Block, yellow
V = 1349.43 (18) Å³	0.55 × 0.47 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3362 independent reflections
Radiation source: fine-focus sealed tube	2711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scan	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
T_min = 0.799, T_max = 0.955	k = −10→9
9504 measured reflections	l = −25→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0641P)² + 0.2074P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3362 reflections	Δρ_max = 0.31 e Å⁻³
185 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0101 (14)

Crystal data top

C₉H₁₂N₂O₇S₂	V = 1349.43 (18) Å³
M_r = 324.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4976 (7) Å	µ = 0.43 mm⁻¹
b = 7.5987 (6) Å	T = 273 K
c = 19.2434 (15) Å	0.55 × 0.47 × 0.11 mm
β = 103.672 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3362 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2711 reflections with I > 2σ(I)
T_min = 0.799, T_max = 0.955	R_int = 0.023
9504 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
3362 reflections	Δρ_min = −0.30 e Å⁻³
185 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
S1	0.80706 (5)	0.21065 (6)	−0.02024 (2)	0.03866 (15)
S2	0.67671 (5)	0.31016 (6)	0.09782 (2)	0.03825 (15)
O1	0.55361 (15)	0.22596 (19)	0.05410 (8)	0.0529 (4)
O2	0.71498 (16)	0.2788 (2)	0.17294 (7)	0.0514 (4)
O3	0.95185 (15)	0.2109 (2)	−0.02879 (7)	0.0522 (4)
O4	0.70649 (16)	0.3355 (2)	−0.05856 (7)	0.0561 (4)
O5	0.80101 (17)	−0.07491 (19)	0.12618 (9)	0.0608 (4)
O6	0.99411 (19)	−0.20742 (17)	0.18046 (9)	0.0602 (4)
O7	1.36416 (14)	0.2232 (2)	0.25913 (8)	0.0503 (4)
N1	0.92993 (18)	−0.07629 (18)	0.15472 (8)	0.0381 (3)
N2	0.82155 (15)	0.24662 (18)	0.06736 (7)	0.0329 (3)
C1	1.14724 (19)	0.0885 (2)	0.20463 (9)	0.0345 (4)
H1B	1.1802	−0.0117	0.2313	0.041*
C2	1.01332 (18)	0.0890 (2)	0.15816 (8)	0.0311 (3)
C3	0.96028 (17)	0.2371 (2)	0.11724 (8)	0.0315 (3)
C4	1.04925 (19)	0.3835 (2)	0.12521 (10)	0.0406 (4)
H4B	1.0171	0.4833	0.0982	0.049*
C5	1.1838 (2)	0.3863 (2)	0.17185 (10)	0.0428 (4)
H5A	1.2407	0.4872	0.1764	0.051*
C6	1.23354 (19)	0.2382 (3)	0.21179 (9)	0.0366 (4)
C7	1.4561 (2)	0.3748 (3)	0.27101 (13)	0.0630 (6)
H7A	1.5458	0.3458	0.3040	0.095*
H7B	1.4090	0.4680	0.2905	0.095*
H7C	1.4752	0.4123	0.2265	0.095*
C8	0.6647 (3)	0.5369 (3)	0.08270 (13)	0.0576 (6)
H8A	0.5830	0.5830	0.0981	0.086*
H8B	0.6528	0.5598	0.0326	0.086*
H8C	0.7517	0.5927	0.1091	0.086*
C9	0.7335 (2)	−0.0003 (3)	−0.03754 (11)	0.0507 (5)
H9A	0.7196	−0.0262	−0.0875	0.076*
H9B	0.6421	−0.0054	−0.0246	0.076*
H9C	0.7986	−0.0849	−0.0100	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0379 (3)	0.0453 (3)	0.0321 (2)	−0.00244 (18)	0.00691 (18)	0.00241 (17)
S2	0.0339 (2)	0.0363 (2)	0.0449 (3)	−0.00356 (16)	0.00994 (18)	−0.00732 (18)
O1	0.0338 (7)	0.0560 (9)	0.0673 (10)	−0.0104 (6)	0.0088 (6)	−0.0157 (7)
O2	0.0573 (9)	0.0568 (9)	0.0437 (8)	−0.0021 (7)	0.0191 (6)	−0.0065 (6)
O3	0.0448 (8)	0.0697 (10)	0.0460 (8)	−0.0059 (7)	0.0185 (6)	−0.0001 (7)
O4	0.0582 (9)	0.0632 (9)	0.0421 (7)	0.0097 (7)	0.0020 (6)	0.0133 (7)
O5	0.0512 (9)	0.0431 (8)	0.0834 (11)	−0.0183 (7)	0.0065 (8)	0.0071 (7)
O6	0.0801 (12)	0.0310 (7)	0.0648 (10)	−0.0038 (7)	0.0078 (8)	0.0130 (7)
O7	0.0351 (7)	0.0564 (9)	0.0529 (8)	−0.0008 (6)	−0.0029 (6)	−0.0013 (7)
N1	0.0530 (9)	0.0287 (7)	0.0343 (7)	−0.0084 (6)	0.0137 (6)	−0.0001 (6)
N2	0.0306 (7)	0.0356 (7)	0.0310 (7)	−0.0017 (6)	0.0044 (5)	−0.0005 (6)
C1	0.0407 (9)	0.0316 (8)	0.0311 (8)	0.0033 (7)	0.0082 (6)	0.0031 (6)
C2	0.0388 (9)	0.0254 (8)	0.0307 (8)	−0.0054 (6)	0.0114 (6)	−0.0010 (6)
C3	0.0323 (8)	0.0300 (8)	0.0317 (8)	−0.0036 (6)	0.0062 (6)	0.0016 (6)
C4	0.0416 (10)	0.0297 (8)	0.0466 (10)	−0.0064 (7)	0.0029 (7)	0.0078 (7)
C5	0.0403 (10)	0.0347 (9)	0.0508 (11)	−0.0112 (7)	0.0054 (8)	0.0039 (8)
C6	0.0336 (9)	0.0417 (9)	0.0337 (9)	−0.0008 (7)	0.0065 (7)	−0.0032 (7)
C7	0.0358 (11)	0.0725 (15)	0.0743 (15)	−0.0108 (10)	0.0002 (10)	−0.0152 (13)
C8	0.0612 (14)	0.0352 (10)	0.0733 (15)	0.0068 (9)	0.0096 (11)	−0.0051 (10)
C9	0.0521 (12)	0.0529 (12)	0.0456 (11)	−0.0100 (9)	0.0089 (9)	−0.0160 (9)

Geometric parameters (Å, º) top

S1—O4	1.4223 (15)	C1—H1B	0.9300
S1—O3	1.4231 (14)	C2—C3	1.397 (2)
S1—N2	1.6809 (14)	C3—C4	1.383 (2)
S1—C9	1.748 (2)	C4—C5	1.377 (2)
S2—O1	1.4210 (14)	C4—H4B	0.9300
S2—O2	1.4247 (14)	C5—C6	1.382 (3)
S2—N2	1.6882 (15)	C5—H5A	0.9300
S2—C8	1.747 (2)	C7—H7A	0.9600
O5—N1	1.218 (2)	C7—H7B	0.9600
O6—N1	1.211 (2)	C7—H7C	0.9600
O7—C6	1.359 (2)	C8—H8A	0.9600
O7—C7	1.431 (3)	C8—H8B	0.9600
N1—C2	1.478 (2)	C8—H8C	0.9600
N2—C3	1.437 (2)	C9—H9A	0.9600
C1—C2	1.371 (2)	C9—H9B	0.9600
C1—C6	1.389 (2)	C9—H9C	0.9600

O4—S1—O3	119.21 (9)	C5—C4—C3	122.23 (16)
O4—S1—N2	107.30 (8)	C5—C4—H4B	118.9
O3—S1—N2	105.27 (8)	C3—C4—H4B	118.9
O4—S1—C9	108.87 (10)	C4—C5—C6	119.50 (17)
O3—S1—C9	109.43 (10)	C4—C5—H5A	120.3
N2—S1—C9	105.93 (9)	C6—C5—H5A	120.3
O1—S2—O2	120.15 (9)	O7—C6—C5	125.38 (17)
O1—S2—N2	106.83 (8)	O7—C6—C1	114.93 (17)
O2—S2—N2	105.73 (8)	C5—C6—C1	119.70 (16)
O1—S2—C8	109.48 (11)	O7—C7—H7A	109.5
O2—S2—C8	108.96 (10)	O7—C7—H7B	109.5
N2—S2—C8	104.52 (10)	H7A—C7—H7B	109.5
C6—O7—C7	117.75 (16)	O7—C7—H7C	109.5
O6—N1—O5	123.14 (15)	H7A—C7—H7C	109.5
O6—N1—C2	117.92 (15)	H7B—C7—H7C	109.5
O5—N1—C2	118.94 (14)	S2—C8—H8A	109.5
C3—N2—S1	120.43 (11)	S2—C8—H8B	109.5
C3—N2—S2	118.43 (11)	H8A—C8—H8B	109.5
S1—N2—S2	120.96 (8)	S2—C8—H8C	109.5
C2—C1—C6	119.80 (16)	H8A—C8—H8C	109.5
C2—C1—H1B	120.1	H8B—C8—H8C	109.5
C6—C1—H1B	120.1	S1—C9—H9A	109.5
C1—C2—C3	121.66 (15)	S1—C9—H9B	109.5
C1—C2—N1	115.57 (14)	H9A—C9—H9B	109.5
C3—C2—N1	122.77 (15)	S1—C9—H9C	109.5
C4—C3—C2	117.11 (15)	H9A—C9—H9C	109.5
C4—C3—N2	118.25 (15)	H9B—C9—H9C	109.5
C2—C3—N2	124.63 (15)

O4—S1—N2—C3	−139.57 (14)	C1—C2—C3—C4	0.4 (2)
O3—S1—N2—C3	−11.63 (15)	N1—C2—C3—C4	−179.79 (15)
C9—S1—N2—C3	104.25 (14)	C1—C2—C3—N2	179.70 (15)
O4—S1—N2—S2	35.55 (12)	N1—C2—C3—N2	−0.5 (3)
O3—S1—N2—S2	163.50 (10)	S1—N2—C3—C4	82.83 (19)
C9—S1—N2—S2	−80.63 (12)	S2—N2—C3—C4	−92.42 (17)
O1—S2—N2—C3	−150.32 (13)	S1—N2—C3—C2	−96.42 (17)
O2—S2—N2—C3	−21.24 (15)	S2—N2—C3—C2	88.33 (19)
C8—S2—N2—C3	93.69 (15)	C2—C3—C4—C5	−0.8 (3)
O1—S2—N2—S1	34.46 (12)	N2—C3—C4—C5	179.87 (17)
O2—S2—N2—S1	163.53 (10)	C3—C4—C5—C6	0.7 (3)
C8—S2—N2—S1	−81.53 (12)	C7—O7—C6—C5	2.6 (3)
C6—C1—C2—C3	0.0 (3)	C7—O7—C6—C1	−177.73 (17)
C6—C1—C2—N1	−179.76 (15)	C4—C5—C6—O7	179.46 (18)
O6—N1—C2—C1	−14.8 (2)	C4—C5—C6—C1	−0.2 (3)
O5—N1—C2—C1	165.47 (17)	C2—C1—C6—O7	−179.86 (15)
O6—N1—C2—C3	165.42 (17)	C2—C1—C6—C5	−0.2 (3)
O5—N1—C2—C3	−14.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱ	0.93	2.46	3.368 (2)	165
C8—H8B···O4	0.96	2.58	3.225 (3)	125
C8—H8C···O5ⁱⁱ	0.96	2.58	3.250 (3)	127
C9—H9B···O1	0.96	2.59	3.226 (3)	124
C9—H9B···O1ⁱⁱⁱ	0.96	2.47	3.173 (3)	130

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

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₇S₂
M_r	324.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	9.4976 (7), 7.5987 (6), 19.2434 (15)
β (°)	103.672 (2)
V (Å³)	1349.43 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.55 × 0.47 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.799, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	9504, 3362, 2711
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.05
No. of reflections	3362
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱ	0.93	2.46	3.368 (2)	165
C8—H8B···O4	0.96	2.58	3.225 (3)	125
C8—H8C···O5ⁱⁱ	0.96	2.58	3.250 (3)	127
C9—H9B···O1	0.96	2.59	3.226 (3)	124
C9—H9B···O1ⁱⁱⁱ	0.96	2.47	3.173 (3)	130

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

References

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