Crystal structure, inter­molecular inter­actions, charge–density distribution and ADME properties of the acridinium 4-nitro­benzoate and 2-amino-3-methyl­pyridinium 4-nitro­benzoate salts: a combined experimental and theoretical study

Acridines are a class of bioactive agents which exhibit high biological stability and the ability to inter­calate with DNA; they have a wide range of applications. Pyridine derivatives have a wide range of biological activities. To enhance the properties of acridine and 2-amino-3-methyl­pyridine as the active pharmaceutical ingredient (API), 4-nitro­benzoic acid was chosen as a coformer. In the present study, a mixture of acridine and 4-nitro­benzoic acid forms the salt acridinium 4-nitro­benzoate, C₁₃H₁₀N⁺·C₇H₄NO₄⁻ (I), whereas a mixture of 2-amino-3-methyl­pyridine and 4-nitro­benzoic acid forms the salt 2-amino-3-methyl­pyridinium 4-nitro­benzoate, C₆H₉N₂⁺·C₇H₄NO₄⁻ (II). In both salts, protonation takes place at the ring N atom. The crystal structure of both salts is predominantly governed by hydrogen-bond inter­actions. In salt I, C—H...O and N—H...O inter­actions form an infinite chain in the crystal, whereas in salt II, inter­molecular N—H...O inter­actions form an eight-membered R₂²(8) ring motif. A theoretical charge–density analysis reveals the charge–density distribution of the inter- and intra­molecular inter­actions of both salts. An in-silico ADME analysis predicts the druglikeness properties of both salts and the results confirm that both salts are potential drug candidates with good bioavailability scores and there is no violation of the Lipinski rules, which supports the druglikeness properties of both salts. However, although both salts exhibit drug-like properties, salt I has higher gastrointestinal absorption than salt II and hence it may be considered a potential drug candidate.

Computing details

Acridin-10-ium 4-nitrobenzoate (I)

Crystal data

C13H10N^+·C7H4NO4^−	Z = 2
Mr = 346.33	F(000) = 360
Triclinic, P1	Dx = 1.395 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6186 (2) Å	Cell parameters from 4100 reflections
b = 9.4985 (2) Å	θ = 2.2–28.3°
c = 11.9173 (3) Å	µ = 0.10 mm^−1
α = 105.380 (1)°	T = 293 K
β = 95.005 (1)°	Block, orange
γ = 93.780 (1)°	0.76 × 0.48 × 0.19 mm
V = 824.77 (3) Å^3

Data collection

Bruker D8 QUEST ECO diffractometer	3338 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.022
Absorption correction: numerical (SADABS; Bruker, 2006)	θmax = 28.0°, θmin = 2.2°
Tmin = 0.697, Tmax = 0.746	h = −10→10
22030 measured reflections	k = −12→12
3965 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: mixed
wR(F^2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0912P)^2 + 0.1205P] where P = (Fo^2 + 2Fc^2)/3
3965 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3
0 constraints

Special details

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. Crystal data, data collection and structure refinement details for salts I and II are summarized in Table 1. The single-crystal X-ray diffraction intensities of both salts were collected at 293 K using a Bruker D8 Quest Eco diffractometer (APEX2, SAINT and SADABS; Bruker, 2006) fitted with an Mo Kα (λ = 0.71073 Å) radiation source. The data processing was carried out with APEX4 software. The structure was solved and refined using the SHELX program incorporated in the WinGX package (Farrugia, 2012). The displacement ellipsoid plots at the 50% probability level were drawn using ORTEP-3 (Farrugia, 2012). The hydrogen-bonding interaction diagram are drawn with Mercury (Macrae et al., 2020). The molecular packing view along the different axes were plotted using PLATON (Spek, 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O3	0.54165 (15)	0.56623 (12)	0.21295 (11)	0.0668 (3)
N2	0.37822 (14)	0.77264 (11)	0.34098 (9)	0.0459 (3)
H2A	0.423114	0.701267	0.295365	0.055*
O4	0.78800 (19)	0.70691 (15)	0.29466 (15)	0.1020 (6)
C20	0.38824 (15)	0.90582 (13)	0.32079 (11)	0.0424 (3)
N1	1.1229 (2)	0.16723 (18)	−0.03261 (13)	0.0718 (4)
O2	1.2828 (2)	0.1862 (2)	−0.00949 (14)	0.1014 (5)
C8	0.29822 (16)	0.75062 (14)	0.43226 (11)	0.0455 (3)
C13	0.22403 (15)	0.86719 (15)	0.51010 (11)	0.0457 (3)
C15	0.31603 (15)	1.02724 (13)	0.39465 (11)	0.0432 (3)
C4	0.81614 (18)	0.48421 (13)	0.15489 (11)	0.0469 (3)
C19	0.47551 (19)	0.92710 (16)	0.22490 (12)	0.0521 (3)
C1	1.01560 (19)	0.27927 (16)	0.03319 (12)	0.0531 (3)
C3	0.73362 (19)	0.35560 (15)	0.07913 (13)	0.0526 (3)
C5	1.0001 (2)	0.50946 (16)	0.16718 (13)	0.0535 (3)
C7	0.7123 (2)	0.59752 (15)	0.22730 (13)	0.0582 (4)
C14	0.23589 (16)	1.00515 (15)	0.48980 (11)	0.0465 (3)
C6	1.10170 (19)	0.40661 (17)	0.10640 (13)	0.0553 (3)
O1	1.0455 (2)	0.06176 (19)	−0.10658 (16)	0.1091 (6)
C2	0.8346 (2)	0.25109 (17)	0.01754 (13)	0.0577 (4)
C12	0.14156 (19)	0.8376 (2)	0.60534 (13)	0.0587 (4)
C16	0.33119 (19)	1.16520 (15)	0.36816 (14)	0.0555 (3)
C18	0.4863 (2)	1.06030 (18)	0.20314 (14)	0.0599 (4)
C9	0.2888 (2)	0.60884 (17)	0.45210 (15)	0.0594 (4)
C11	0.1319 (2)	0.7003 (2)	0.62023 (16)	0.0690 (5)
C17	0.4128 (2)	1.18062 (17)	0.27497 (15)	0.0616 (4)
C10	0.2070 (2)	0.5862 (2)	0.54345 (17)	0.0688 (4)
H12	0.100 (2)	0.9205 (18)	0.6581 (14)	0.053 (4)*
H16	0.285 (2)	1.245 (2)	0.4182 (16)	0.067 (5)*
H6	1.226 (3)	0.426 (2)	0.1128 (17)	0.080 (6)*
H3	0.607 (3)	0.337 (2)	0.0702 (16)	0.071 (5)*
H14	0.192 (2)	1.0847 (18)	0.5403 (14)	0.055 (4)*
H19	0.527 (2)	0.8461 (19)	0.1765 (15)	0.062 (4)*
H2	0.776 (3)	0.167 (2)	−0.0305 (18)	0.075 (5)*
H17	0.423 (3)	1.272 (2)	0.2600 (18)	0.088 (6)*
H5	1.054 (2)	0.595 (2)	0.2226 (17)	0.070 (5)*
H18	0.549 (3)	1.074 (2)	0.1385 (18)	0.078 (5)*
H9	0.343 (2)	0.534 (2)	0.3967 (15)	0.063 (5)*
H11	0.073 (3)	0.681 (2)	0.683 (2)	0.093 (7)*
H10	0.202 (3)	0.488 (3)	0.5555 (19)	0.092 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0631 (6)	0.0509 (6)	0.0779 (7)	0.0097 (5)	0.0155 (5)	−0.0007 (5)
N2	0.0461 (6)	0.0383 (5)	0.0486 (6)	0.0067 (4)	0.0062 (4)	0.0027 (4)
O4	0.0806 (9)	0.0662 (8)	0.1208 (12)	0.0135 (6)	−0.0072 (8)	−0.0367 (8)
C20	0.0361 (5)	0.0422 (6)	0.0449 (6)	0.0045 (4)	0.0014 (4)	0.0057 (5)
N1	0.0776 (10)	0.0801 (10)	0.0628 (8)	0.0247 (7)	0.0295 (7)	0.0173 (7)
O2	0.0743 (9)	0.1417 (14)	0.0901 (10)	0.0447 (9)	0.0312 (7)	0.0194 (9)
C8	0.0399 (6)	0.0438 (6)	0.0482 (6)	0.0012 (5)	−0.0006 (5)	0.0071 (5)
C13	0.0330 (5)	0.0552 (7)	0.0459 (6)	0.0044 (5)	0.0010 (4)	0.0096 (5)
C15	0.0341 (5)	0.0413 (6)	0.0502 (6)	0.0070 (4)	0.0008 (5)	0.0061 (5)
C4	0.0544 (7)	0.0405 (6)	0.0453 (6)	0.0056 (5)	0.0033 (5)	0.0110 (5)
C19	0.0515 (7)	0.0545 (7)	0.0491 (7)	0.0077 (6)	0.0092 (5)	0.0105 (6)
C1	0.0586 (8)	0.0563 (8)	0.0484 (7)	0.0128 (6)	0.0159 (6)	0.0161 (6)
C3	0.0479 (7)	0.0476 (7)	0.0574 (7)	0.0019 (5)	0.0074 (6)	0.0060 (6)
C5	0.0571 (8)	0.0474 (7)	0.0524 (7)	−0.0018 (6)	−0.0051 (6)	0.0122 (6)
C7	0.0681 (9)	0.0429 (7)	0.0580 (8)	0.0101 (6)	0.0015 (6)	0.0046 (6)
C14	0.0367 (6)	0.0488 (7)	0.0490 (7)	0.0117 (5)	0.0046 (5)	0.0029 (5)
C6	0.0477 (7)	0.0653 (8)	0.0566 (8)	0.0027 (6)	0.0046 (6)	0.0240 (7)
O1	0.1137 (12)	0.0870 (10)	0.1081 (12)	0.0211 (9)	0.0423 (10)	−0.0182 (9)
C2	0.0599 (8)	0.0483 (7)	0.0564 (8)	0.0014 (6)	0.0090 (6)	−0.0003 (6)
C12	0.0442 (7)	0.0802 (10)	0.0519 (7)	0.0088 (6)	0.0071 (6)	0.0169 (7)
C16	0.0504 (7)	0.0427 (7)	0.0712 (9)	0.0117 (5)	0.0036 (6)	0.0110 (6)
C18	0.0578 (8)	0.0665 (9)	0.0587 (8)	0.0030 (7)	0.0077 (6)	0.0232 (7)
C9	0.0628 (8)	0.0470 (7)	0.0656 (9)	0.0008 (6)	0.0014 (7)	0.0132 (6)
C11	0.0548 (8)	0.0949 (13)	0.0659 (9)	−0.0008 (8)	0.0068 (7)	0.0387 (9)
C17	0.0603 (8)	0.0517 (8)	0.0767 (10)	0.0052 (6)	0.0018 (7)	0.0260 (7)
C10	0.0680 (10)	0.0659 (10)	0.0759 (10)	−0.0070 (8)	−0.0005 (8)	0.0310 (8)

Geometric parameters (Å, º)

O3—C7	1.3002 (19)	C1—C2	1.374 (2)
N2—C20	1.3475 (17)	C1—C6	1.375 (2)
N2—C8	1.3484 (17)	C3—C2	1.389 (2)
N2—H2A	0.86	C3—H3	0.96 (2)
O4—C7	1.2061 (18)	C5—C6	1.379 (2)
C20—C19	1.4235 (19)	C5—H5	0.943 (19)
C20—C15	1.4273 (17)	C14—H14	0.934 (17)
N1—O2	1.216 (2)	C6—H6	0.95 (2)
N1—O1	1.221 (2)	C2—H2	0.91 (2)
N1—C1	1.4833 (19)	C12—C11	1.360 (3)
C8—C9	1.426 (2)	C12—H12	0.959 (17)
C8—C13	1.4267 (18)	C16—C17	1.355 (2)
C13—C14	1.3929 (19)	C16—H16	0.941 (19)
C13—C12	1.426 (2)	C18—C17	1.415 (2)
C15—C14	1.3903 (19)	C18—H18	0.98 (2)
C15—C16	1.4269 (19)	C9—C10	1.358 (2)
C4—C3	1.3847 (18)	C9—H9	0.973 (18)
C4—C5	1.3944 (19)	C11—C10	1.410 (3)
C4—C7	1.5060 (19)	C11—H11	0.96 (2)
C19—C18	1.356 (2)	C17—H17	0.93 (2)
C19—H19	0.962 (18)	C10—H10	0.98 (2)
C20—N2—C8	120.39 (11)	O4—C7—O3	124.39 (14)
C20—N2—H2A	119.8	O4—C7—C4	120.17 (15)
C8—N2—H2A	119.8	O3—C7—C4	115.43 (12)
N2—C20—C19	119.44 (11)	C15—C14—C13	120.40 (11)
N2—C20—C15	121.55 (11)	C15—C14—H14	118.8 (10)
C19—C20—C15	119.01 (12)	C13—C14—H14	120.8 (10)
O2—N1—O1	124.04 (16)	C1—C6—C5	117.81 (13)
O2—N1—C1	117.87 (16)	C1—C6—H6	121.7 (12)
O1—N1—C1	118.09 (16)	C5—C6—H6	120.4 (12)
N2—C8—C9	119.56 (12)	C1—C2—C3	118.54 (13)
N2—C8—C13	121.10 (12)	C1—C2—H2	124.2 (13)
C9—C8—C13	119.34 (13)	C3—C2—H2	117.3 (13)
C14—C13—C12	122.91 (13)	C11—C12—C13	120.44 (15)
C14—C13—C8	118.46 (12)	C11—C12—H12	123.8 (10)
C12—C13—C8	118.63 (13)	C13—C12—H12	115.7 (10)
C14—C15—C16	123.29 (12)	C17—C16—C15	120.66 (13)
C14—C15—C20	118.08 (12)	C17—C16—H16	121.3 (11)
C16—C15—C20	118.62 (12)	C15—C16—H16	118.0 (11)
C3—C4—C5	119.82 (12)	C19—C18—C17	121.12 (14)
C3—C4—C7	121.61 (12)	C19—C18—H18	119.4 (12)
C5—C4—C7	118.55 (12)	C17—C18—H18	119.4 (12)
C18—C19—C20	120.18 (13)	C10—C9—C8	119.63 (15)
C18—C19—H19	120.7 (11)	C10—C9—H9	124.9 (11)
C20—C19—H19	119.1 (11)	C8—C9—H9	115.5 (11)
C2—C1—C6	123.12 (13)	C12—C11—C10	120.49 (15)
C2—C1—N1	118.36 (14)	C12—C11—H11	119.4 (14)
C6—C1—N1	118.52 (14)	C10—C11—H11	120.1 (14)
C4—C3—C2	119.86 (13)	C16—C17—C18	120.40 (14)
C4—C3—H3	120.5 (11)	C16—C17—H17	119.1 (13)
C2—C3—H3	119.6 (11)	C18—C17—H17	120.5 (13)
C6—C5—C4	120.83 (13)	C9—C10—C11	121.46 (16)
C6—C5—H5	120.4 (12)	C9—C10—H10	118.3 (13)
C4—C5—H5	118.6 (11)	C11—C10—H10	120.2 (13)
C8—N2—C20—C19	179.11 (11)	C3—C4—C7—O3	−0.4 (2)
C8—N2—C20—C15	0.24 (18)	C5—C4—C7—O3	−179.01 (12)
C20—N2—C8—C9	179.94 (11)	C16—C15—C14—C13	179.41 (11)
C20—N2—C8—C13	−0.61 (18)	C20—C15—C14—C13	−1.30 (18)
N2—C8—C13—C14	0.02 (18)	C12—C13—C14—C15	−179.23 (11)
C9—C8—C13—C14	179.46 (11)	C8—C13—C14—C15	0.96 (18)
N2—C8—C13—C12	−179.80 (11)	C2—C1—C6—C5	0.5 (2)
C9—C8—C13—C12	−0.35 (19)	N1—C1—C6—C5	−179.82 (12)
N2—C20—C15—C14	0.71 (18)	C4—C5—C6—C1	0.3 (2)
C19—C20—C15—C14	−178.16 (11)	C6—C1—C2—C3	−0.5 (2)
N2—C20—C15—C16	−179.96 (11)	N1—C1—C2—C3	179.89 (13)
C19—C20—C15—C16	1.16 (18)	C4—C3—C2—C1	−0.5 (2)
N2—C20—C19—C18	179.78 (12)	C14—C13—C12—C11	179.22 (12)
C15—C20—C19—C18	−1.3 (2)	C8—C13—C12—C11	−1.0 (2)
O2—N1—C1—C2	−172.69 (15)	C14—C15—C16—C17	179.15 (13)
O1—N1—C1—C2	7.3 (2)	C20—C15—C16—C17	−0.1 (2)
O2—N1—C1—C6	7.7 (2)	C20—C19—C18—C17	0.4 (2)
O1—N1—C1—C6	−172.34 (16)	N2—C8—C9—C10	−179.46 (13)
C5—C4—C3—C2	1.3 (2)	C13—C8—C9—C10	1.1 (2)
C7—C4—C3—C2	−177.31 (13)	C13—C12—C11—C10	1.6 (2)
C3—C4—C5—C6	−1.2 (2)	C15—C16—C17—C18	−0.8 (2)
C7—C4—C5—C6	177.41 (12)	C19—C18—C17—C16	0.6 (2)
C3—C4—C7—O4	178.20 (17)	C8—C9—C10—C11	−0.5 (3)
C5—C4—C7—O4	−0.4 (2)	C12—C11—C10—C9	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	1.75	2.6055 (16)	172
C14—H14···O4^i	0.934 (17)	2.378 (17)	3.245 (2)	154.5 (13)
C19—H19···O2^ii	0.960 (17)	2.529 (16)	3.280 (2)	135.2 (14)

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

2-Amino-3-methylpyridinium 4-nitrobenzoate (II)

Crystal data

C6H9N2^+·C7H4NO4^−	F(000) = 288
Mr = 275.26	Dx = 1.389 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.2555 (6) Å	Cell parameters from 9892 reflections
b = 6.7520 (5) Å	θ = 2.5–41.2°
c = 11.8096 (9) Å	µ = 0.11 mm^−1
β = 90.573 (3)°	T = 296 K
V = 658.25 (8) Å^3	Block, green
Z = 2	0.61 × 0.25 × 0.09 mm

Data collection

Bruker D8 QUEST ECO diffractometer	3220 independent reflections
Radiation source: fine-focus sealed tube	3103 reflections with I > 2σ(I)
Flat graphite monochromator	Rint = 0.042
Detector resolution: 7.3910 pixels mm^-1	θmax = 28.3°, θmin = 2.5°
ω and φ scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2019)	k = −8→8
Tmin = 0.88, Tmax = 0.99	l = −15→15
3220 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.2428P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.132	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.20 e Å^−3
3220 reflections	Δρmin = −0.20 e Å^−3
183 parameters	Absolute structure: Flack x determined using 1304 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.2 (4)

Special details

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. Refined as a 2-component twin.

Crystal data, data collection and structure refinement details for salts I and II are summarized in Table 1. The single-crystal X-ray diffraction intensities of both salts were collected at 293 K using a Bruker D8 Quest Eco diffractometer (APEX2, SAINT and SADABS; Bruker, 2006) fitted with an Mo Kα (λ = 0.71073 Å) radiation source. The data processing was carried out with APEX4 software. The structure was solved and refined using the SHELX program incorporated in the WinGX package (Farrugia, 2012). The displacement ellipsoid plots at the 50% probability level were drawn using ORTEP-3 (Farrugia, 2012). The hydrogen-bonding interaction diagram are drawn with Mercury (Macrae et al., 2020). The molecular packing view along the different axes were plotted using PLATON (Spek, 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0396 (5)	−0.2408 (5)	0.6185 (3)	0.0832 (12)
O2	0.6228 (4)	0.6303 (4)	0.6901 (2)	0.0533 (7)
O3	1.0303 (6)	−0.2949 (6)	0.7960 (4)	0.0892 (13)
O4	0.6033 (4)	0.5723 (4)	0.8745 (2)	0.0501 (7)
N1	0.9984 (4)	−0.1964 (5)	0.7132 (3)	0.0541 (8)
N2	0.4405 (4)	0.9520 (4)	0.6964 (2)	0.0387 (6)
H2	0.497074	0.845216	0.699183	0.046000*
N3	0.4237 (4)	0.9352 (5)	0.8900 (2)	0.0461 (7)
H3A	0.478651	0.827091	0.888073	0.055000*
H3B	0.391797	0.981768	0.953816	0.055000*
C1	0.9075 (4)	−0.0095 (5)	0.7295 (3)	0.0413 (8)
C2	0.8807 (5)	0.1111 (5)	0.6373 (3)	0.0433 (8)
H2A	0.916881	0.075756	0.565794	0.052000*
C3	0.7984 (5)	0.2861 (5)	0.6544 (3)	0.0427 (8)
H3	0.779833	0.370723	0.593538	0.051000*
C4	0.7426 (4)	0.3382 (5)	0.7612 (3)	0.0354 (6)
C5	0.7730 (5)	0.2121 (5)	0.8521 (3)	0.0466 (9)
H5	0.737050	0.246140	0.923878	0.056000*
C6	0.8566 (5)	0.0362 (6)	0.8365 (3)	0.0499 (9)
H6	0.877530	−0.048478	0.897027	0.060000*
C7	0.6486 (4)	0.5290 (5)	0.7776 (3)	0.0377 (7)
C8	0.3879 (4)	1.0307 (5)	0.7941 (3)	0.0340 (6)
C9	0.4080 (5)	1.0340 (6)	0.5937 (3)	0.0451 (8)
H9	0.447081	0.974297	0.528509	0.054000*
C10	0.3192 (5)	1.2018 (6)	0.5854 (3)	0.0455 (8)
H10	0.294489	1.257178	0.515248	0.055000*
C11	0.2658 (5)	1.2894 (6)	0.6852 (3)	0.0442 (8)
H11	0.207084	1.406720	0.680712	0.053000*
C12	0.2967 (4)	1.2091 (5)	0.7894 (3)	0.0374 (7)
C13	0.2384 (5)	1.3027 (6)	0.8969 (3)	0.0513 (10)
H13A	0.158245	1.401184	0.879204	0.077000*
H13B	0.328065	1.363709	0.935807	0.077000*
H13C	0.191738	1.202947	0.944456	0.077000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.115 (3)	0.057 (2)	0.078 (2)	0.033 (2)	0.031 (2)	−0.0108 (18)
O2	0.087 (2)	0.0374 (13)	0.0362 (12)	0.0226 (13)	0.0090 (13)	0.0051 (10)
O3	0.119 (3)	0.062 (2)	0.087 (2)	0.048 (2)	0.006 (2)	0.011 (2)
O4	0.0782 (18)	0.0395 (13)	0.0328 (11)	0.0149 (13)	0.0069 (12)	0.0009 (10)
N1	0.060 (2)	0.0342 (16)	0.068 (2)	0.0113 (15)	0.0077 (17)	0.0005 (15)
N2	0.0487 (15)	0.0337 (13)	0.0339 (13)	0.0074 (12)	0.0010 (12)	−0.0036 (11)
N3	0.066 (2)	0.0406 (15)	0.0323 (13)	0.0127 (14)	0.0026 (13)	−0.0005 (12)
C1	0.0420 (17)	0.0295 (16)	0.052 (2)	0.0027 (13)	0.0049 (14)	0.0000 (14)
C2	0.052 (2)	0.0429 (19)	0.0348 (15)	0.0040 (16)	0.0056 (14)	−0.0040 (14)
C3	0.057 (2)	0.0379 (17)	0.0329 (16)	0.0055 (16)	0.0032 (14)	0.0062 (14)
C4	0.0444 (17)	0.0274 (14)	0.0345 (15)	0.0014 (12)	0.0020 (12)	0.0004 (12)
C5	0.067 (2)	0.0387 (18)	0.0348 (16)	0.0104 (17)	0.0105 (16)	0.0063 (15)
C6	0.069 (2)	0.0398 (19)	0.0413 (18)	0.0139 (18)	0.0108 (16)	0.0149 (16)
C7	0.0510 (18)	0.0273 (15)	0.0347 (15)	0.0029 (14)	0.0029 (13)	0.0013 (12)
C8	0.0401 (15)	0.0291 (14)	0.0328 (14)	−0.0006 (13)	0.0002 (12)	−0.0031 (12)
C9	0.055 (2)	0.051 (2)	0.0287 (14)	0.0001 (18)	−0.0006 (13)	−0.0031 (14)
C10	0.059 (2)	0.0458 (18)	0.0314 (15)	0.0040 (17)	−0.0040 (14)	0.0052 (14)
C11	0.0475 (19)	0.0390 (17)	0.0460 (19)	0.0127 (16)	−0.0056 (15)	0.0006 (15)
C12	0.0417 (17)	0.0372 (16)	0.0333 (15)	0.0027 (14)	−0.0015 (12)	−0.0055 (13)
C13	0.066 (2)	0.048 (2)	0.0407 (18)	0.0200 (19)	0.0025 (17)	−0.0085 (16)

Geometric parameters (Å, º)

O1—N1	1.210 (5)	C2—C3	1.378 (5)
O2—C7	1.255 (4)	C3—C4	1.392 (4)
O3—N1	1.209 (5)	C4—C5	1.391 (5)
O4—C7	1.242 (4)	C4—C7	1.518 (4)
N1—C1	1.482 (4)	C5—C6	1.387 (5)
N2—C8	1.346 (4)	C8—C12	1.421 (4)
N2—C9	1.358 (4)	C9—C10	1.352 (5)
N3—C8	1.334 (4)	C10—C11	1.394 (5)
C1—C6	1.371 (5)	C11—C12	1.366 (5)
C1—C2	1.375 (5)	C12—C13	1.501 (5)
O3—N1—O1	123.4 (4)	C1—C6—C5	118.2 (3)
O3—N1—C1	118.0 (4)	O4—C7—O2	125.4 (3)
O1—N1—C1	118.5 (3)	O4—C7—C4	118.5 (3)
C8—N2—C9	122.8 (3)	O2—C7—C4	116.1 (3)
C6—C1—C2	123.2 (3)	N3—C8—N2	117.8 (3)
C6—C1—N1	118.1 (3)	N3—C8—C12	123.7 (3)
C2—C1—N1	118.6 (3)	N2—C8—C12	118.5 (3)
C1—C2—C3	117.8 (3)	C10—C9—N2	120.5 (3)
C2—C3—C4	121.1 (3)	C9—C10—C11	118.0 (3)
C5—C4—C3	119.1 (3)	C12—C11—C10	122.4 (3)
C5—C4—C7	120.6 (3)	C11—C12—C8	117.7 (3)
C3—C4—C7	120.3 (3)	C11—C12—C13	122.4 (3)
C6—C5—C4	120.5 (3)	C8—C12—C13	119.9 (3)
O3—N1—C1—C6	−3.6 (6)	C3—C4—C7—O4	−178.7 (4)
O1—N1—C1—C6	177.8 (4)	C5—C4—C7—O2	−177.9 (4)
O3—N1—C1—C2	175.3 (4)	C3—C4—C7—O2	1.4 (5)
O1—N1—C1—C2	−3.3 (6)	C9—N2—C8—N3	178.4 (3)
C6—C1—C2—C3	0.0 (6)	C9—N2—C8—C12	−1.1 (5)
N1—C1—C2—C3	−178.9 (3)	C8—N2—C9—C10	−0.1 (6)
C1—C2—C3—C4	−0.7 (6)	N2—C9—C10—C11	1.4 (6)
C2—C3—C4—C5	1.0 (6)	C9—C10—C11—C12	−1.7 (6)
C2—C3—C4—C7	−178.4 (3)	C10—C11—C12—C8	0.5 (5)
C3—C4—C5—C6	−0.5 (6)	C10—C11—C12—C13	−179.6 (4)
C7—C4—C5—C6	178.9 (4)	N3—C8—C12—C11	−178.7 (3)
C2—C1—C6—C5	0.5 (6)	N2—C8—C12—C11	0.8 (5)
N1—C1—C6—C5	179.3 (4)	N3—C8—C12—C13	1.5 (5)
C4—C5—C6—C1	−0.2 (6)	N2—C8—C12—C13	−179.0 (3)
C5—C4—C7—O4	1.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.79	2.6444 (4)	174
N3—H3A···O4	0.86	2.01	2.871 (4)	177
N3—H3B···O4^i	0.86	2.12	2.942 (3)	160
C2—H2A···O1^ii	0.93	2.53	3.256 (5)	135
C13—H13A···O3^iii	0.96	2.50	3.422 (6)	160

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