4-Bromo-N-(2-nitro-phen-yl)benzamide.

The title nitro-phenyl benzamide, C13H9BrN2O3, with two mol-ecules in the asymmetric unit, has dihedral angles of 16.78 (15) and 18.87 (14)° between the benzene rings. An intra-molecular N-H⋯O hydrogen bond is observed in each mol-ecule. In the crystal, the molecules are linked by weak C-H⋯O inter-actions; halogen-halogen inter-actions are also observed [Br⋯Br = 3.4976 (7) Å]. These inter-actions form R (2) 2(10), R (2) 2(15) and R (6) 6(32) edge-fused rings along [010].

Related literature

For properties of amide compounds, see: Bisson et al. (2000 ▶). For the anti­bacterial and anti­fungal activity of amide compounds, see: Aytemir et al. (2003 ▶). For similar compounds, see: Moreno-Fuquen et al. (2013 ▶); Sripet et al. (2012 ▶). For halogen–halogen inter­actions, see: Awwadi et al. (2006 ▶); For hydrogen-bonding information, see: Nardelli (1995 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C13H9BrN2O3

M = 321.13

Triclinic,

a = 3.8338 (4) Å

b = 12.6784 (13) Å

c = 24.918 (2) Å

α = 81.875 (8)°

β = 88.386 (7)°

γ = 85.460 (8)°

V = 1195.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.45 mm−1

T = 123 K

0.49 × 0.05 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010 ▶; analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.380, T max = 0.914

9979 measured reflections

9979 independent reflections

7814 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.04

9979 reflections

344 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.77 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814003298/gg2134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003298/gg2134Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003298/gg2134Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H9BrN2O3	Z = 4
Mr = 321.13	F(000) = 640
Triclinic, P1	Dx = 1.785 Mg m−3
Hall symbol: -P 1	Melting point: 423(1) K
a = 3.8338 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.6784 (13) Å	Cell parameters from 4010 reflections
c = 24.918 (2) Å	θ = 3.1–28.0°
α = 81.875 (8)°	µ = 3.45 mm−1
β = 88.386 (7)°	T = 123 K
γ = 85.460 (8)°	Needle, yellow
V = 1195.1 (2) Å3	0.49 × 0.05 × 0.03 mm

Oxford Diffraction Xcalibur E diffractometer	9979 independent reflections
Radiation source: fine-focus sealed tube	7814 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
ω scans	θmax = 27.0°, θmin = 3.2°
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010; analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)]	h = −4→4
Tmin = 0.380, Tmax = 0.914	k = −14→16
9979 measured reflections	l = −31→31

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) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0479P)2 + 3.1562P] where P = (Fo2 + 2Fc2)/3
9979 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 0.62 e Å−3
1 restraint	Δρmin = −0.77 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	−0.49930 (10)	0.56740 (4)	0.433729 (18)	0.02208 (13)
Br2	0.96920 (10)	0.05996 (4)	0.084392 (18)	0.02296 (13)
O1	0.2537 (8)	0.8253 (2)	0.20551 (12)	0.0270 (7)
O2	−0.0265 (8)	0.4919 (3)	0.14483 (13)	0.0334 (8)
O3	0.1224 (9)	0.4476 (3)	0.06706 (14)	0.0384 (9)
O4	0.4069 (8)	0.3367 (3)	0.29067 (13)	0.0313 (8)
O5	−0.0468 (8)	−0.0126 (2)	0.35060 (13)	0.0312 (8)
O6	−0.3517 (8)	−0.0460 (2)	0.42413 (13)	0.0285 (8)
N1	0.1677 (9)	0.6691 (3)	0.17304 (14)	0.0202 (8)
H1N	0.0934	0.6052	0.1830	0.024*
N2	0.1123 (9)	0.5117 (3)	0.09994 (16)	0.0229 (9)
N3	0.2077 (8)	0.1750 (3)	0.32592 (14)	0.0197 (8)
H3N	0.1732	0.1120	0.3170	0.024*
N4	−0.1642 (9)	0.0120 (3)	0.39439 (15)	0.0209 (8)
C1	−0.3041 (10)	0.6174 (3)	0.36484 (17)	0.0168 (9)
C2	−0.2476 (11)	0.7244 (3)	0.35235 (18)	0.0214 (10)
H2	−0.3098	0.7727	0.3775	0.026*
C3	−0.0988 (10)	0.7599 (4)	0.30253 (18)	0.0215 (10)
H3	−0.0561	0.8331	0.2937	0.026*
C4	−0.0101 (10)	0.6895 (3)	0.26489 (17)	0.0158 (9)
C5	−0.0678 (10)	0.5813 (3)	0.27900 (17)	0.0180 (9)
H5	−0.0041	0.5321	0.2543	0.022*
C6	−0.2171 (10)	0.5459 (3)	0.32875 (17)	0.0201 (10)
H6	−0.2598	0.4728	0.3381	0.024*
C7	0.1510 (10)	0.7357 (3)	0.21253 (18)	0.0194 (10)
C8	0.2861 (10)	0.6897 (3)	0.11986 (17)	0.0173 (9)
C9	0.2622 (10)	0.6145 (3)	0.08342 (18)	0.0186 (9)
C10	0.3722 (10)	0.6340 (3)	0.02913 (17)	0.0194 (10)
H10	0.3486	0.5824	0.0056	0.023*
C11	0.5139 (10)	0.7282 (3)	0.01035 (18)	0.0212 (10)
H11	0.5915	0.7424	−0.0263	0.025*
C12	0.5432 (10)	0.8028 (4)	0.04532 (18)	0.0228 (10)
H12	0.6411	0.8682	0.0321	0.027*
C13	0.4345 (10)	0.7847 (3)	0.09874 (18)	0.0193 (10)
H13	0.4604	0.8375	0.1216	0.023*
C14	0.7748 (10)	0.1158 (3)	0.14657 (17)	0.0177 (9)
C15	0.7605 (10)	0.2246 (3)	0.14817 (18)	0.0200 (10)
H15	0.8432	0.2718	0.1183	0.024*
C16	0.6236 (10)	0.2633 (3)	0.19396 (18)	0.0213 (10)
H16	0.6128	0.3378	0.1957	0.026*
C17	0.5013 (10)	0.1945 (3)	0.23763 (17)	0.0184 (10)
C18	0.5160 (10)	0.0848 (3)	0.23493 (18)	0.0193 (10)
H18	0.4291	0.0375	0.2644	0.023*
C19	0.6571 (10)	0.0450 (4)	0.18936 (18)	0.0202 (10)
H19	0.6726	−0.0296	0.1875	0.024*
C20	0.3678 (11)	0.2434 (4)	0.28646 (18)	0.0194 (10)
C21	0.0933 (10)	0.1912 (3)	0.37755 (17)	0.0180 (9)
C22	−0.0783 (10)	0.1120 (3)	0.41268 (18)	0.0187 (10)
C23	−0.1763 (10)	0.1250 (3)	0.46513 (18)	0.0204 (10)
H23	−0.2880	0.0701	0.4875	0.024*
C24	−0.1133 (11)	0.2167 (4)	0.48520 (18)	0.0233 (10)
H24	−0.1778	0.2254	0.5215	0.028*
C25	0.0461 (10)	0.2968 (3)	0.45179 (18)	0.0198 (10)
H25	0.0882	0.3608	0.4654	0.024*
C26	0.1440 (10)	0.2850 (3)	0.39935 (18)	0.0197 (10)
H26	0.2486	0.3418	0.3773	0.024*

	U11	U22	U33	U12	U13	U23
Br1	0.0215 (2)	0.0273 (3)	0.0174 (3)	−0.00393 (18)	0.00245 (17)	−0.00226 (19)
Br2	0.0207 (2)	0.0277 (3)	0.0208 (3)	−0.00279 (18)	0.00324 (17)	−0.0047 (2)
O1	0.0428 (19)	0.0170 (18)	0.0223 (19)	−0.0113 (14)	0.0046 (15)	−0.0028 (14)
O2	0.052 (2)	0.031 (2)	0.020 (2)	−0.0187 (16)	0.0162 (16)	−0.0100 (15)
O3	0.067 (2)	0.020 (2)	0.032 (2)	−0.0136 (17)	0.0130 (18)	−0.0141 (16)
O4	0.047 (2)	0.021 (2)	0.028 (2)	−0.0090 (15)	0.0118 (15)	−0.0079 (15)
O5	0.049 (2)	0.027 (2)	0.020 (2)	−0.0157 (15)	0.0125 (15)	−0.0091 (15)
O6	0.0359 (18)	0.0234 (19)	0.028 (2)	−0.0123 (14)	0.0114 (15)	−0.0056 (15)
N1	0.029 (2)	0.014 (2)	0.018 (2)	−0.0049 (15)	0.0032 (16)	−0.0033 (15)
N2	0.029 (2)	0.016 (2)	0.024 (2)	−0.0024 (16)	−0.0005 (17)	−0.0049 (17)
N3	0.0251 (19)	0.014 (2)	0.020 (2)	−0.0045 (15)	0.0007 (15)	−0.0029 (16)
N4	0.0220 (19)	0.021 (2)	0.019 (2)	−0.0017 (15)	−0.0012 (16)	0.0000 (17)
C1	0.014 (2)	0.022 (3)	0.014 (2)	−0.0017 (17)	0.0008 (16)	−0.0008 (18)
C2	0.024 (2)	0.023 (3)	0.019 (3)	−0.0006 (19)	0.0036 (18)	−0.010 (2)
C3	0.025 (2)	0.017 (2)	0.024 (3)	−0.0035 (18)	−0.0004 (19)	−0.0044 (19)
C4	0.018 (2)	0.013 (2)	0.016 (2)	−0.0002 (16)	−0.0023 (17)	−0.0016 (17)
C5	0.024 (2)	0.016 (2)	0.016 (2)	−0.0044 (17)	0.0020 (18)	−0.0056 (18)
C6	0.022 (2)	0.016 (2)	0.022 (3)	−0.0012 (17)	−0.0036 (18)	−0.0041 (19)
C7	0.019 (2)	0.019 (3)	0.019 (3)	0.0025 (18)	−0.0001 (17)	−0.0024 (19)
C8	0.013 (2)	0.019 (2)	0.019 (3)	−0.0009 (16)	−0.0022 (17)	−0.0006 (18)
C9	0.020 (2)	0.015 (2)	0.021 (3)	−0.0043 (17)	0.0003 (18)	−0.0019 (18)
C10	0.022 (2)	0.017 (2)	0.019 (3)	−0.0009 (17)	0.0042 (18)	−0.0031 (18)
C11	0.021 (2)	0.029 (3)	0.012 (2)	−0.0021 (18)	0.0040 (17)	0.0013 (19)
C12	0.021 (2)	0.022 (3)	0.025 (3)	−0.0058 (18)	0.0020 (19)	−0.001 (2)
C13	0.023 (2)	0.015 (2)	0.019 (3)	−0.0040 (17)	0.0042 (18)	−0.0027 (18)
C14	0.015 (2)	0.021 (3)	0.017 (2)	−0.0007 (17)	0.0004 (17)	−0.0050 (18)
C15	0.019 (2)	0.023 (3)	0.017 (3)	−0.0059 (18)	0.0026 (18)	−0.0010 (19)
C16	0.021 (2)	0.012 (2)	0.029 (3)	−0.0024 (17)	−0.0003 (19)	0.0019 (19)
C17	0.016 (2)	0.020 (3)	0.020 (3)	−0.0047 (17)	−0.0015 (17)	−0.0037 (19)
C18	0.021 (2)	0.018 (2)	0.018 (3)	−0.0022 (17)	0.0030 (18)	−0.0002 (19)
C19	0.018 (2)	0.019 (3)	0.024 (3)	−0.0033 (17)	−0.0022 (18)	−0.0030 (19)
C20	0.022 (2)	0.020 (3)	0.017 (3)	−0.0017 (18)	−0.0008 (18)	−0.0041 (19)
C21	0.015 (2)	0.020 (3)	0.018 (2)	0.0002 (17)	−0.0015 (17)	0.0011 (18)
C22	0.016 (2)	0.016 (2)	0.025 (3)	0.0016 (16)	−0.0027 (18)	−0.0042 (19)
C23	0.022 (2)	0.019 (3)	0.020 (3)	0.0008 (18)	0.0001 (18)	−0.0035 (19)
C24	0.021 (2)	0.030 (3)	0.018 (3)	0.0067 (19)	−0.0013 (18)	−0.006 (2)
C25	0.020 (2)	0.017 (2)	0.024 (3)	0.0017 (17)	−0.0022 (18)	−0.0094 (19)
C26	0.024 (2)	0.015 (2)	0.020 (3)	−0.0010 (17)	0.0020 (18)	−0.0014 (18)

Br1—C1	1.898 (4)	C9—C10	1.400 (6)
Br2—C14	1.902 (4)	C10—C11	1.368 (6)
O1—C7	1.219 (5)	C10—H10	0.9500
O2—N2	1.227 (5)	C11—C12	1.386 (6)
O3—N2	1.230 (5)	C11—H11	0.9500
O4—C20	1.223 (5)	C12—C13	1.377 (6)
O5—N4	1.239 (5)	C12—H12	0.9500
O6—N4	1.227 (4)	C13—H13	0.9500
N1—C7	1.382 (5)	C14—C15	1.383 (6)
N1—C8	1.385 (5)	C14—C19	1.383 (6)
N1—H1N	0.8800	C15—C16	1.378 (6)
N2—C9	1.467 (5)	C15—H15	0.9500
N3—C20	1.380 (5)	C16—C17	1.390 (6)
N3—C21	1.385 (5)	C16—H16	0.9500
N3—H3N	0.8800	C17—C18	1.399 (6)
N4—C22	1.470 (5)	C17—C20	1.502 (6)
C1—C6	1.381 (6)	C18—C19	1.386 (6)
C1—C2	1.382 (6)	C18—H18	0.9500
C2—C3	1.383 (6)	C19—H19	0.9500
C2—H2	0.9500	C21—C26	1.404 (6)
C3—C4	1.401 (6)	C21—C22	1.425 (6)
C3—H3	0.9500	C22—C23	1.378 (6)
C4—C5	1.400 (6)	C23—C24	1.370 (6)
C4—C7	1.491 (6)	C23—H23	0.9500
C5—C6	1.382 (6)	C24—C25	1.388 (6)
C5—H5	0.9500	C24—H24	0.9500
C6—H6	0.9500	C25—C26	1.374 (6)
C8—C13	1.402 (6)	C25—H25	0.9500
C8—C9	1.415 (6)	C26—H26	0.9500
C7—N1—C8	128.5 (4)	C13—C12—C11	121.9 (4)
C7—N1—H1N	115.8	C13—C12—H12	119.1
C8—N1—H1N	115.8	C11—C12—H12	119.1
O2—N2—O3	121.3 (4)	C12—C13—C8	120.9 (4)
O2—N2—C9	120.5 (4)	C12—C13—H13	119.5
O3—N2—C9	118.1 (4)	C8—C13—H13	119.5
C20—N3—C21	129.4 (4)	C15—C14—C19	122.1 (4)
C20—N3—H3N	115.3	C15—C14—Br2	119.6 (3)
C21—N3—H3N	115.3	C19—C14—Br2	118.3 (3)
O6—N4—O5	121.7 (4)	C16—C15—C14	118.6 (4)
O6—N4—C22	117.7 (4)	C16—C15—H15	120.7
O5—N4—C22	120.6 (4)	C14—C15—H15	120.7
C6—C1—C2	121.5 (4)	C15—C16—C17	120.8 (4)
C6—C1—Br1	119.4 (3)	C15—C16—H16	119.6
C2—C1—Br1	119.0 (3)	C17—C16—H16	119.6
C1—C2—C3	118.7 (4)	C16—C17—C18	119.5 (4)
C1—C2—H2	120.6	C16—C17—C20	117.1 (4)
C3—C2—H2	120.6	C18—C17—C20	123.4 (4)
C2—C3—C4	121.0 (4)	C19—C18—C17	120.1 (4)
C2—C3—H3	119.5	C19—C18—H18	120.0
C4—C3—H3	119.5	C17—C18—H18	120.0
C5—C4—C3	118.8 (4)	C14—C19—C18	118.8 (4)
C5—C4—C7	124.4 (4)	C14—C19—H19	120.6
C3—C4—C7	116.7 (4)	C18—C19—H19	120.6
C6—C5—C4	120.1 (4)	O4—C20—N3	123.4 (4)
C6—C5—H5	119.9	O4—C20—C17	121.5 (4)
C4—C5—H5	119.9	N3—C20—C17	115.1 (4)
C1—C6—C5	119.7 (4)	N3—C21—C26	122.7 (4)
C1—C6—H6	120.1	N3—C21—C22	121.8 (4)
C5—C6—H6	120.1	C26—C21—C22	115.4 (4)
O1—C7—N1	123.6 (4)	C23—C22—C21	122.3 (4)
O1—C7—C4	122.3 (4)	C23—C22—N4	116.4 (4)
N1—C7—C4	114.2 (4)	C21—C22—N4	121.4 (4)
N1—C8—C13	122.8 (4)	C24—C23—C22	120.3 (4)
N1—C8—C9	121.2 (4)	C24—C23—H23	119.8
C13—C8—C9	116.0 (4)	C22—C23—H23	119.8
C10—C9—C8	122.5 (4)	C23—C24—C25	119.1 (4)
C10—C9—N2	115.5 (4)	C23—C24—H24	120.4
C8—C9—N2	122.0 (4)	C25—C24—H24	120.4
C11—C10—C9	119.3 (4)	C26—C25—C24	121.2 (4)
C11—C10—H10	120.4	C26—C25—H25	119.4
C9—C10—H10	120.4	C24—C25—H25	119.4
C10—C11—C12	119.4 (4)	C25—C26—C21	121.7 (4)
C10—C11—H11	120.3	C25—C26—H26	119.2
C12—C11—H11	120.3	C21—C26—H26	119.2
O2—O2—N2—O3	0.0 (3)	N1—C8—C13—C12	−178.8 (3)
O2—O2—N2—C9	0.0 (4)	C9—C8—C13—C12	1.0 (5)
O5—O5—N4—O6	0.0 (12)	C19—C14—C15—C16	−0.1 (6)
O5—O5—N4—C22	0.0 (13)	Br2—C14—C15—C16	−179.0 (3)
C6—C1—C2—C3	−0.3 (6)	C14—C15—C16—C17	−0.2 (6)
Br1—C1—C2—C3	178.7 (3)	C15—C16—C17—C18	−0.3 (6)
C1—C2—C3—C4	0.8 (6)	C15—C16—C17—C20	178.0 (4)
C2—C3—C4—C5	−1.4 (6)	C16—C17—C18—C19	1.1 (6)
C2—C3—C4—C7	−179.6 (3)	C20—C17—C18—C19	−177.1 (4)
C3—C4—C5—C6	1.5 (6)	C15—C14—C19—C18	0.9 (6)
C7—C4—C5—C6	179.6 (3)	Br2—C14—C19—C18	179.8 (3)
C2—C1—C6—C5	0.4 (6)	C17—C18—C19—C14	−1.4 (5)
Br1—C1—C6—C5	−178.6 (3)	C21—N3—C20—O4	−6.5 (6)
C4—C5—C6—C1	−1.0 (6)	C21—N3—C20—C17	172.1 (3)
C8—N1—C7—O1	−2.2 (6)	C16—C17—C20—O4	−9.4 (6)
C8—N1—C7—C4	176.8 (3)	C18—C17—C20—O4	168.8 (4)
C5—C4—C7—O1	−166.6 (4)	C16—C17—C20—N3	172.0 (3)
C3—C4—C7—O1	11.5 (6)	C18—C17—C20—N3	−9.8 (5)
C5—C4—C7—N1	14.3 (5)	C20—N3—C21—C26	−3.4 (6)
C3—C4—C7—N1	−167.5 (3)	C20—N3—C21—C22	178.0 (4)
C7—N1—C8—C13	4.4 (6)	N3—C21—C22—C23	176.4 (3)
C7—N1—C8—C9	−175.5 (4)	C26—C21—C22—C23	−2.3 (5)
N1—C8—C9—C10	178.5 (3)	N3—C21—C22—N4	−4.3 (5)
C13—C8—C9—C10	−1.4 (6)	C26—C21—C22—N4	177.0 (3)
N1—C8—C9—N2	−0.1 (6)	O6—N4—C22—C23	8.7 (5)
C13—C8—C9—N2	−179.9 (3)	O5—N4—C22—C23	−170.6 (3)
O2—N2—C9—C10	−172.0 (4)	O5—N4—C22—C23	−170.6 (3)
O2—N2—C9—C10	−172.0 (4)	O6—N4—C22—C21	−170.6 (3)
O3—N2—C9—C10	6.2 (5)	O5—N4—C22—C21	10.1 (5)
O2—N2—C9—C8	6.7 (6)	O5—N4—C22—C21	10.1 (5)
O2—N2—C9—C8	6.7 (6)	C21—C22—C23—C24	0.7 (6)
O3—N2—C9—C8	−175.1 (4)	N4—C22—C23—C24	−178.6 (3)
C8—C9—C10—C11	1.1 (6)	C22—C23—C24—C25	0.8 (6)
N2—C9—C10—C11	179.8 (3)	C23—C24—C25—C26	−0.6 (6)
C9—C10—C11—C12	−0.5 (6)	C24—C25—C26—C21	−1.1 (6)
C10—C11—C12—C13	0.2 (6)	N3—C21—C26—C25	−176.2 (3)
C11—C12—C13—C8	−0.5 (6)	C22—C21—C26—C25	2.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4i	0.95	2.65	3.378 (5)	134
C16—H16···O2ii	0.95	2.64	3.349 (5)	132
C19—H19···O1iii	0.95	2.52	3.262 (5)	135
C3—H3···O5iv	0.95	2.58	3.299 (5)	133
C23—H23···O6v	0.95	2.56	3.334 (5)	139
N1—H1N···O2	0.88	1.92	2.615 (5)	134
N3—H3N···O5	0.88	1.92	2.628 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4i	0.95	2.65	3.378 (5)	134
C16—H16⋯O2ii	0.95	2.64	3.349 (5)	132
C19—H19⋯O1iii	0.95	2.52	3.262 (5)	135
C3—H3⋯O5iv	0.95	2.58	3.299 (5)	133
C23—H23⋯O6v	0.95	2.56	3.334 (5)	139
N1—H1N⋯O2	0.88	1.92	2.615 (5)	134
N3—H3N⋯O5	0.88	1.92	2.628 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .