Crystal structure of 5,5'-[(4-fluoro-phen-yl)methyl-ene]bis-[6-amino-1,3-di-methyl-pyrimidine-2,4(1H,3H)-dione].

In the title mol-ecule, C19H21FN6O4, the dihedral angles between the benzene ring and essentially planar pyrimidine rings [maximum deviations of 0.036 (2) and 0.056 (2) Å] are 73.32 (7) and 63.81 (8)°. The dihedral angle between the mean planes of the pyrimidine rings is 61.43 (6)°. In the crystal, N-H⋯O hydrogen bonds link mol-ecules, forming a two-dimensional network parallel to (001) and in combination with weak C-H⋯O hydrogen bonds, a three-dimensional network is formed. Weak C-H⋯π inter-actions and π-π inter-actions, with a centroid-centroid distance of 3.599 (2) Å are also observed.

Related literature

For the biological activity of uracil derivatives, see: Muller et al. (1993 ▶); Buckle et al. (1994 ▶). For drugs containing purine moieties, see: Zhi et al. (2003 ▶); Devi & Bhuyan (2005 ▶). For the biological activity of pyrimidine scaffolds, see: Makarov et al. (2005 ▶); Deshmukh et al. (2009 ▶); Ibrahim & El-Metwally (2010 ▶). For the synthesis of bis-uracil derivatives, see: Karimi et al. (2013 ▶). For a related structure, see: Das et al. (2009 ▶).

Experimental

Crystal data

C19H21FN6O4

M = 416.42

Orthorhombic,

a = 14.6208 (6) Å

b = 11.3324 (7) Å

c = 22.6410 (12) Å

V = 3751.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.862, T max = 1.000

9655 measured reflections

3665 independent reflections

2208 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.130

S = 1.04

3665 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814019886/lh5725sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019886/lh5725Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019886/lh5725Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019886/lh5725fig1.tif

The mol­ecular structure with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

Click here for additional data file.

a . DOI: 10.1107/S1600536814019886/lh5725fig2.tif

Part of the crystal structure viewed along the a axis. Hydrogen bonds are shown as dashed lines.

CCDC reference: 973485

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

C19H21FN6O4	F(000) = 1744
Mr = 416.42	Dx = 1.475 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2766 reflections
a = 14.6208 (6) Å	θ = 4.0–29.0°
b = 11.3324 (7) Å	µ = 0.11 mm−1
c = 22.6410 (12) Å	T = 293 K
V = 3751.4 (3) Å3	Rectangular, white
Z = 8	0.30 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3665 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −17→18
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→10
Tmin = 0.862, Tmax = 1.000	l = −27→27
9655 measured reflections

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) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.280P] where P = (Fo2 + 2Fc2)/3
3665 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
O3A	0.12040 (11)	0.70286 (16)	0.47999 (8)	0.0448 (5)
O3A'	0.41972 (12)	0.90382 (17)	0.35851 (8)	0.0481 (5)
N3	0.21150 (13)	0.67789 (19)	0.56011 (9)	0.0385 (5)
N1'	0.27279 (15)	0.63863 (19)	0.28860 (9)	0.0445 (6)
C5'	0.28708 (16)	0.7846 (2)	0.36460 (10)	0.0336 (6)
N1	0.35782 (12)	0.7609 (2)	0.56448 (9)	0.0388 (5)
C5	0.26609 (15)	0.7945 (2)	0.47801 (10)	0.0317 (6)
N18	0.16272 (16)	0.6468 (2)	0.36253 (12)	0.0445 (6)
O2	0.29971 (14)	0.6586 (2)	0.64250 (9)	0.0697 (7)
C4	0.25464 (16)	0.8542 (2)	0.41822 (10)	0.0337 (6)
H4	0.2992	0.9187	0.4203	0.040*
C6	0.34765 (15)	0.8050 (2)	0.50801 (10)	0.0328 (6)
C6'	0.24099 (18)	0.6903 (2)	0.34020 (11)	0.0374 (6)
N15	0.42224 (15)	0.8593 (2)	0.48533 (11)	0.0410 (6)
C7	0.16385 (16)	0.9204 (2)	0.41091 (11)	0.0323 (6)
C3A'	0.37186 (18)	0.8189 (2)	0.34004 (11)	0.0393 (6)
N3'	0.40473 (15)	0.7555 (2)	0.29207 (9)	0.0465 (6)
C3A	0.19584 (17)	0.7257 (2)	0.50409 (11)	0.0366 (6)
F20	−0.06866 (11)	1.12341 (16)	0.39325 (9)	0.0834 (7)
C2	0.28952 (18)	0.6969 (3)	0.59256 (12)	0.0437 (7)
O2'	0.39032 (16)	0.60699 (19)	0.22495 (9)	0.0746 (7)
C2'	0.3585 (2)	0.6640 (3)	0.26558 (12)	0.0503 (8)
C13	0.44207 (17)	0.7825 (3)	0.59804 (11)	0.0499 (8)
H13A	0.4918	0.7404	0.5801	0.075*
H13B	0.4341	0.7558	0.6380	0.075*
H13C	0.4554	0.8655	0.5980	0.075*
C12	0.13307 (17)	0.9921 (2)	0.45682 (12)	0.0441 (7)
H12	0.1651	0.9932	0.4923	0.053*
C8	0.11561 (17)	0.9230 (2)	0.35843 (12)	0.0405 (7)
H8	0.1362	0.8786	0.3265	0.049*
C10	0.00938 (18)	1.0575 (2)	0.39853 (15)	0.0505 (8)
C11	0.05596 (19)	1.0616 (3)	0.45075 (14)	0.0510 (8)
H11	0.0363	1.1098	0.4815	0.061*
C9	0.03704 (18)	0.9907 (2)	0.35245 (14)	0.0502 (8)
H9	0.0040	0.9900	0.3174	0.060*
C14	0.14123 (18)	0.6033 (3)	0.58682 (13)	0.0536 (8)
H14A	0.1677	0.5579	0.6183	0.080*
H14B	0.1167	0.5509	0.5575	0.080*
H14C	0.0931	0.6519	0.6022	0.080*
C17	0.4962 (2)	0.7837 (3)	0.26916 (14)	0.0683 (10)
H17A	0.5409	0.7351	0.2885	0.102*
H17B	0.5096	0.8653	0.2766	0.102*
H17C	0.4979	0.7690	0.2274	0.102*
C16	0.2188 (2)	0.5502 (3)	0.25638 (13)	0.0626 (9)
H16A	0.2378	0.5486	0.2158	0.094*
H16B	0.1551	0.5704	0.2585	0.094*
H16C	0.2283	0.4739	0.2738	0.094*
H60	0.1393 (18)	0.576 (3)	0.3509 (12)	0.057 (9)*
H50	0.1483 (16)	0.675 (2)	0.4000 (13)	0.049 (8)*
H40	0.4206 (17)	0.880 (2)	0.4441 (13)	0.060 (9)*
H30	0.476 (2)	0.856 (3)	0.5011 (13)	0.069 (10)*

	U11	U22	U33	U12	U13	U23
O3A	0.0359 (10)	0.0609 (13)	0.0376 (10)	−0.0095 (9)	−0.0013 (8)	0.0047 (10)
O3A'	0.0439 (10)	0.0557 (12)	0.0446 (11)	−0.0059 (10)	0.0066 (9)	0.0039 (11)
N3	0.0360 (11)	0.0470 (14)	0.0326 (11)	−0.0023 (10)	0.0028 (10)	0.0068 (12)
N1'	0.0635 (15)	0.0365 (13)	0.0335 (12)	0.0040 (11)	0.0064 (11)	0.0008 (11)
C5'	0.0385 (14)	0.0364 (15)	0.0259 (12)	0.0042 (12)	0.0025 (11)	0.0036 (12)
N1	0.0311 (11)	0.0530 (15)	0.0322 (11)	0.0047 (10)	−0.0026 (9)	0.0040 (12)
C5	0.0263 (12)	0.0375 (15)	0.0313 (12)	0.0021 (11)	0.0015 (11)	0.0023 (12)
N18	0.0511 (15)	0.0398 (15)	0.0424 (14)	−0.0043 (12)	0.0052 (13)	−0.0045 (13)
O2	0.0658 (14)	0.1013 (19)	0.0420 (12)	−0.0168 (13)	−0.0105 (11)	0.0299 (13)
C4	0.0340 (13)	0.0350 (15)	0.0320 (13)	0.0015 (12)	−0.0005 (11)	0.0012 (12)
C6	0.0320 (13)	0.0355 (14)	0.0310 (13)	0.0041 (11)	−0.0008 (11)	−0.0001 (12)
C6'	0.0450 (15)	0.0349 (15)	0.0324 (13)	0.0090 (13)	0.0004 (12)	0.0048 (13)
N15	0.0305 (12)	0.0565 (15)	0.0361 (13)	−0.0035 (11)	−0.0025 (11)	0.0055 (12)
C7	0.0302 (13)	0.0315 (14)	0.0352 (14)	0.0001 (11)	0.0000 (11)	0.0043 (12)
C3A'	0.0466 (16)	0.0409 (16)	0.0306 (13)	0.0059 (13)	0.0038 (13)	0.0092 (14)
N3'	0.0534 (14)	0.0510 (15)	0.0349 (12)	0.0043 (12)	0.0139 (11)	0.0073 (12)
C3A	0.0380 (14)	0.0399 (16)	0.0320 (13)	0.0041 (12)	0.0000 (12)	−0.0005 (13)
F20	0.0666 (12)	0.0682 (13)	0.1154 (17)	0.0373 (10)	−0.0044 (11)	0.0026 (13)
C2	0.0443 (16)	0.0500 (18)	0.0366 (15)	0.0012 (14)	0.0019 (13)	0.0050 (15)
O2'	0.1086 (18)	0.0632 (15)	0.0521 (13)	0.0067 (13)	0.0384 (13)	−0.0086 (13)
C2'	0.071 (2)	0.0446 (18)	0.0354 (15)	0.0101 (16)	0.0139 (15)	0.0097 (15)
C13	0.0360 (14)	0.078 (2)	0.0360 (14)	0.0019 (15)	−0.0102 (12)	0.0074 (16)
C12	0.0468 (16)	0.0436 (17)	0.0420 (16)	0.0021 (13)	0.0006 (13)	−0.0035 (14)
C8	0.0459 (15)	0.0344 (15)	0.0414 (15)	0.0067 (12)	−0.0041 (13)	0.0006 (13)
C10	0.0418 (16)	0.0333 (16)	0.076 (2)	0.0096 (13)	0.0004 (16)	0.0073 (17)
C11	0.0578 (18)	0.0398 (17)	0.0554 (19)	0.0045 (14)	0.0075 (16)	−0.0067 (16)
C9	0.0519 (17)	0.0431 (17)	0.0556 (18)	0.0095 (14)	−0.0143 (15)	0.0051 (16)
C14	0.0539 (18)	0.060 (2)	0.0474 (17)	−0.0143 (15)	0.0038 (14)	0.0125 (17)
C17	0.0648 (19)	0.082 (3)	0.0577 (18)	0.0027 (18)	0.0337 (16)	0.008 (2)
C16	0.095 (3)	0.0499 (19)	0.0431 (17)	−0.0025 (18)	0.0072 (17)	−0.0099 (17)

O3A—C3A	1.257 (3)	C7—C12	1.394 (3)
O3A'—C3A'	1.261 (3)	C3A'—N3'	1.388 (3)
N3—C2	1.374 (3)	N3'—C2'	1.376 (3)
N3—C3A	1.398 (3)	N3'—C17	1.470 (3)
N3—C14	1.462 (3)	F20—C10	1.369 (3)
N1'—C2'	1.387 (3)	O2'—C2'	1.217 (3)
N1'—C6'	1.387 (3)	C13—H13A	0.9600
N1'—C16	1.469 (3)	C13—H13B	0.9600
C5'—C6'	1.379 (3)	C13—H13C	0.9600
C5'—C3A'	1.413 (3)	C12—C11	1.382 (4)
C5'—C4	1.523 (3)	C12—H12	0.9300
N1—C6	1.381 (3)	C8—C9	1.388 (3)
N1—C2	1.388 (3)	C8—H8	0.9300
N1—C13	1.468 (3)	C10—C9	1.351 (4)
C5—C6	1.377 (3)	C10—C11	1.365 (4)
C5—C3A	1.419 (3)	C11—H11	0.9300
C5—C4	1.522 (3)	C9—H9	0.9300
N18—C6'	1.345 (3)	C14—H14A	0.9600
N18—H60	0.91 (3)	C14—H14B	0.9600
N18—H50	0.93 (3)	C14—H14C	0.9600
O2—C2	1.220 (3)	C17—H17A	0.9600
C4—C7	1.533 (3)	C17—H17B	0.9600
C4—H4	0.9800	C17—H17C	0.9600
C6—N15	1.354 (3)	C16—H16A	0.9600
N15—H40	0.96 (3)	C16—H16B	0.9600
N15—H30	0.87 (3)	C16—H16C	0.9600
C7—C8	1.382 (3)
C2—N3—C3A	124.1 (2)	O2—C2—N3	122.8 (3)
C2—N3—C14	116.9 (2)	O2—C2—N1	121.5 (3)
C3A—N3—C14	119.0 (2)	N3—C2—N1	115.7 (2)
C2'—N1'—C6'	122.1 (2)	O2'—C2'—N3'	122.8 (3)
C2'—N1'—C16	116.1 (2)	O2'—C2'—N1'	121.3 (3)
C6'—N1'—C16	121.8 (2)	N3'—C2'—N1'	115.9 (2)
C6'—C5'—C3A'	119.0 (2)	N1—C13—H13A	109.5
C6'—C5'—C4	124.6 (2)	N1—C13—H13B	109.5
C3A'—C5'—C4	116.4 (2)	H13A—C13—H13B	109.5
C6—N1—C2	122.4 (2)	N1—C13—H13C	109.5
C6—N1—C13	120.6 (2)	H13A—C13—H13C	109.5
C2—N1—C13	117.0 (2)	H13B—C13—H13C	109.5
C6—C5—C3A	118.0 (2)	C11—C12—C7	121.4 (3)
C6—C5—C4	119.7 (2)	C11—C12—H12	119.3
C3A—C5—C4	122.3 (2)	C7—C12—H12	119.3
C6'—N18—H60	122.2 (17)	C7—C8—C9	121.2 (3)
C6'—N18—H50	114.3 (16)	C7—C8—H8	119.4
H60—N18—H50	119 (2)	C9—C8—H8	119.4
C5—C4—C5'	116.4 (2)	C9—C10—C11	122.6 (3)
C5—C4—C7	114.11 (19)	C9—C10—F20	119.2 (3)
C5'—C4—C7	115.9 (2)	C11—C10—F20	118.2 (3)
C5—C4—H4	102.5	C10—C11—C12	118.3 (3)
C5'—C4—H4	102.5	C10—C11—H11	120.9
C7—C4—H4	102.5	C12—C11—H11	120.9
N15—C6—C5	123.3 (2)	C10—C9—C8	118.8 (3)
N15—C6—N1	115.4 (2)	C10—C9—H9	120.6
C5—C6—N1	121.2 (2)	C8—C9—H9	120.6
N18—C6'—C5'	123.3 (2)	N3—C14—H14A	109.5
N18—C6'—N1'	116.6 (2)	N3—C14—H14B	109.5
C5'—C6'—N1'	120.1 (2)	H14A—C14—H14B	109.5
C6—N15—H40	117.4 (16)	N3—C14—H14C	109.5
C6—N15—H30	124 (2)	H14A—C14—H14C	109.5
H40—N15—H30	116 (3)	H14B—C14—H14C	109.5
C8—C7—C12	117.6 (2)	N3'—C17—H17A	109.5
C8—C7—C4	123.0 (2)	N3'—C17—H17B	109.5
C12—C7—C4	119.0 (2)	H17A—C17—H17B	109.5
O3A'—C3A'—N3'	117.6 (2)	N3'—C17—H17C	109.5
O3A'—C3A'—C5'	124.5 (2)	H17A—C17—H17C	109.5
N3'—C3A'—C5'	118.0 (2)	H17B—C17—H17C	109.5
C2'—N3'—C3A'	124.1 (2)	N1'—C16—H16A	109.5
C2'—N3'—C17	117.2 (2)	N1'—C16—H16B	109.5
C3A'—N3'—C17	118.6 (2)	H16A—C16—H16B	109.5
O3A—C3A—N3	117.2 (2)	N1'—C16—H16C	109.5
O3A—C3A—C5	124.6 (2)	H16A—C16—H16C	109.5
N3—C3A—C5	118.2 (2)	H16B—C16—H16C	109.5
C6—C5—C4—C5'	86.2 (3)	C5'—C3A'—N3'—C17	−175.0 (2)
C3A—C5—C4—C5'	−92.6 (3)	C2—N3—C3A—O3A	−178.5 (2)
C6—C5—C4—C7	−134.7 (2)	C14—N3—C3A—O3A	1.2 (4)
C3A—C5—C4—C7	46.5 (3)	C2—N3—C3A—C5	2.5 (4)
C6'—C5'—C4—C5	75.3 (3)	C14—N3—C3A—C5	−177.9 (2)
C3A'—C5'—C4—C5	−102.8 (3)	C6—C5—C3A—O3A	−175.5 (2)
C6'—C5'—C4—C7	−63.1 (3)	C4—C5—C3A—O3A	3.4 (4)
C3A'—C5'—C4—C7	118.8 (2)	C6—C5—C3A—N3	3.5 (4)
C3A—C5—C6—N15	173.9 (2)	C4—C5—C3A—N3	−177.7 (2)
C4—C5—C6—N15	−4.9 (4)	C3A—N3—C2—O2	176.5 (3)
C3A—C5—C6—N1	−6.9 (4)	C14—N3—C2—O2	−3.2 (4)
C4—C5—C6—N1	174.3 (2)	C3A—N3—C2—N1	−4.8 (4)
C2—N1—C6—N15	−176.2 (2)	C14—N3—C2—N1	175.5 (2)
C13—N1—C6—N15	5.1 (3)	C6—N1—C2—O2	−180.0 (3)
C2—N1—C6—C5	4.6 (4)	C13—N1—C2—O2	−1.3 (4)
C13—N1—C6—C5	−174.1 (2)	C6—N1—C2—N3	1.3 (4)
C3A'—C5'—C6'—N18	176.0 (2)	C13—N1—C2—N3	−179.9 (2)
C4—C5'—C6'—N18	−2.1 (4)	C3A'—N3'—C2'—O2'	−177.2 (3)
C3A'—C5'—C6'—N1'	−6.9 (4)	C17—N3'—C2'—O2'	0.2 (4)
C4—C5'—C6'—N1'	175.0 (2)	C3A'—N3'—C2'—N1'	1.8 (4)
C2'—N1'—C6'—N18	−171.0 (2)	C17—N3'—C2'—N1'	179.3 (2)
C16—N1'—C6'—N18	6.6 (4)	C6'—N1'—C2'—O2'	170.1 (2)
C2'—N1'—C6'—C5'	11.7 (4)	C16—N1'—C2'—O2'	−7.6 (4)
C16—N1'—C6'—C5'	−170.7 (2)	C6'—N1'—C2'—N3'	−8.9 (4)
C5—C4—C7—C8	−142.5 (2)	C16—N1'—C2'—N3'	173.4 (2)
C5'—C4—C7—C8	−3.2 (3)	C8—C7—C12—C11	1.4 (4)
C5—C4—C7—C12	44.9 (3)	C4—C7—C12—C11	174.4 (2)
C5'—C4—C7—C12	−175.8 (2)	C12—C7—C8—C9	−2.7 (4)
C6'—C5'—C3A'—O3A'	179.7 (2)	C4—C7—C8—C9	−175.4 (2)
C4—C5'—C3A'—O3A'	−2.0 (4)	C9—C10—C11—C12	−1.6 (4)
C6'—C5'—C3A'—N3'	0.1 (4)	F20—C10—C11—C12	177.9 (2)
C4—C5'—C3A'—N3'	178.3 (2)	C7—C12—C11—C10	0.7 (4)
O3A'—C3A'—N3'—C2'	−177.2 (2)	C11—C10—C9—C8	0.3 (4)
C5'—C3A'—N3'—C2'	2.4 (4)	F20—C10—C9—C8	−179.2 (2)
O3A'—C3A'—N3'—C17	5.4 (3)	C7—C8—C9—C10	1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H40···O3A′	0.96 (3)	1.96 (3)	2.916 (3)	174 (2)
N18—H50···O3A	0.93 (3)	1.88 (3)	2.803 (3)	170 (2)
N15—H30···O3Ai	0.86 (3)	2.26 (3)	3.083 (3)	161 (3)
N18—H60···O3A′ii	0.91 (3)	2.14 (3)	3.007 (3)	159 (2)
C13—H13A···O3Ai	0.96	2.41	3.154 (3)	134
C13—H13A···Cgiii	0.96	2.98	3.744 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N15—H40⋯O3A′	0.96 (3)	1.96 (3)	2.916 (3)	174 (2)
N18—H50⋯O3A	0.93 (3)	1.88 (3)	2.803 (3)	170 (2)
N15—H30⋯O3A i	0.86 (3)	2.26 (3)	3.083 (3)	161 (3)
N18—H60⋯O3A′ii	0.91 (3)	2.14 (3)	3.007 (3)	159 (2)
C13—H13A⋯O3A i	0.96	2.41	3.154 (3)	134
C13—H13A⋯Cg iii	0.96	2.98	3.744 (3)	138

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