2,4-Diamino-5-(3,4,5-trimethoxy­benz­yl)pyrimidinium 4-hydr­oxy-3-nitrophenyl-arsonate monohydrate

The crystal structure of the title compound, (C₁₄H₁₉N₄O₃)[AsO₂(OH)(C₆H₄NO₃)]·H₂O, consists of substituted pyrimidine cations, roxarsone (3-nitro-4-hydr­oxyphenyl­arsonate) anions and water mol­ecules. Due to deprotonation of the arsonate group, the As—O bond distances in the anion are significantly different. An extensive network of O—H...O, N—H...O and N—H...N hydrogen bonds helps to stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.119
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N1

Alert level C
PLAT213_ALERT_2_C Atom O5A     has ADP max/min Ratio .............       3.30 prola
PLAT213_ALERT_2_C Atom O5B     has ADP max/min Ratio .............       3.60 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.74
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C14H19N4O3·C6H5AsNO6·H2O	F(000) = 2352
Mr = 571.38	Dx = 1.565 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15356 reflections
a = 8.1865 (13) Å	θ = 2.2–25.2°
b = 20.9285 (16) Å	µ = 1.47 mm^−1
c = 28.304 (2) Å	T = 294 K
V = 4849.3 (9) Å^3	Prism, yellow
Z = 8	0.34 × 0.30 × 0.25 mm

Data collection

Bruker APEX II diffractometer	4489 independent reflections
Radiation source: fine-focus sealed tube	3922 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	h = −9→9
Tmin = 0.622, Tmax = 0.700	k = −25→23
24891 measured reflections	l = −29→34

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: difmap and geom
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 5.6729P] where P = (Fo^2 + 2Fc^2)/3
4489 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
As	0.13857 (4)	0.079784 (17)	0.018532 (13)	0.02743 (14)
N1	0.4029 (5)	0.2364 (2)	0.14004 (14)	0.0512 (10)
N2	0.1960 (4)	0.26052 (16)	0.00154 (12)	0.0382 (8)
H2A	0.1443	0.2199	0.0012	0.057*
H2B	0.3015	0.2634	−0.0131	0.057*
N3	−0.1562 (4)	0.32426 (18)	0.11841 (12)	0.0469 (9)
H3A	−0.1829	0.3565	0.1393	0.070*
H3B	−0.2224	0.2898	0.1116	0.070*
N4	0.0147 (4)	0.29321 (15)	0.05902 (11)	0.0333 (7)
N5	0.2462 (4)	0.35461 (16)	0.04058 (10)	0.0333 (7)
H5A	0.3421	0.3627	0.0235	0.050*
O1	0.2200 (3)	0.03098 (14)	−0.02431 (9)	0.0443 (7)
H1	0.1294	0.0124	−0.0389	0.067*
O2	0.0245 (3)	0.03543 (14)	0.05449 (9)	0.0429 (7)
O3	0.0383 (4)	0.14112 (13)	−0.00401 (12)	0.0490 (8)
O4	0.7178 (3)	0.18306 (14)	0.12672 (10)	0.0451 (7)
H4A	0.8102	0.1586	0.1239	0.068*
O5A	0.5041 (10)	0.2753 (5)	0.1478 (6)	0.085 (5)	0.60 (3)
O6A	0.2608 (14)	0.2436 (9)	0.1536 (7)	0.111 (6)	0.60 (3)
O5B	0.482 (3)	0.2350 (17)	0.1785 (8)	0.136 (14)	0.40 (3)
O6B	0.303 (3)	0.2719 (9)	0.1348 (6)	0.087 (8)	0.40 (3)
O7	0.2024 (4)	0.35980 (14)	0.27862 (9)	0.0455 (7)
O8	0.1198 (3)	0.46733 (15)	0.32319 (9)	0.0439 (7)
O9	−0.0217 (5)	0.56423 (16)	0.27743 (11)	0.0625 (10)
O1W	0.9565 (4)	0.10540 (14)	0.13160 (10)	0.0456 (7)
H1A	0.9886	0.0820	0.1084	0.068*
H1B	0.9462	0.0787	0.1559	0.068*
C1	0.3258 (4)	0.11069 (17)	0.05114 (12)	0.0261 (8)
C2	0.4810 (5)	0.08592 (17)	0.04496 (13)	0.0313 (8)
H2	0.4969	0.0529	0.0234	0.038*
C3	0.6119 (4)	0.10895 (18)	0.06988 (13)	0.0322 (8)
H3	0.7148	0.0912	0.0652	0.039*
C4	0.5925 (5)	0.15888 (18)	0.10219 (13)	0.0308 (8)
C5	0.4358 (5)	0.18346 (18)	0.10778 (13)	0.0321 (9)
C6	0.3028 (5)	0.15973 (17)	0.08284 (13)	0.0305 (8)
H6	0.1992	0.1768	0.0875	0.037*
C7	−0.0271 (5)	0.33696 (19)	0.09109 (13)	0.0319 (9)
C8	0.1517 (5)	0.30230 (18)	0.03420 (13)	0.0311 (8)
C9	0.1967 (5)	0.40142 (19)	0.07022 (13)	0.0340 (9)
H9	0.2596	0.4383	0.0727	0.041*
C10	0.0590 (5)	0.39663 (18)	0.09637 (12)	0.0309 (8)
C11	−0.0010 (5)	0.4511 (2)	0.12613 (13)	0.0397 (10)
H11A	−0.1187	0.4533	0.1224	0.048*
H11B	0.0437	0.4901	0.1129	0.048*
C12	0.0349 (5)	0.45144 (19)	0.17873 (13)	0.0338 (9)
C13	0.1072 (5)	0.40140 (19)	0.20259 (13)	0.0343 (9)
H13	0.1379	0.3646	0.1864	0.041*
C14	0.1340 (5)	0.40630 (19)	0.25116 (14)	0.0346 (9)
C15	0.0890 (5)	0.4613 (2)	0.27529 (13)	0.0376 (10)
C16	0.0172 (5)	0.5112 (2)	0.25090 (15)	0.0424 (10)
C17	−0.0093 (5)	0.5067 (2)	0.20278 (14)	0.0424 (10)
H17	−0.0568	0.5406	0.1865	0.051*
C18	0.2569 (7)	0.3034 (2)	0.25595 (17)	0.0565 (13)
H18A	0.1659	0.2825	0.2411	0.085*
H18B	0.3046	0.2752	0.2789	0.085*
H18C	0.3370	0.3141	0.2325	0.085*
C19	−0.0036 (6)	0.4390 (2)	0.35189 (15)	0.0511 (12)
H19A	−0.1054	0.4607	0.3469	0.077*
H19B	0.0269	0.4423	0.3845	0.077*
H19C	−0.0155	0.3947	0.3436	0.077*
C20	−0.1030 (8)	0.6156 (3)	0.2553 (2)	0.083 (2)
H20A	−0.0318	0.6349	0.2324	0.125*
H20B	−0.1329	0.6468	0.2786	0.125*
H20C	−0.1995	0.6001	0.2398	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As	0.0261 (2)	0.0261 (2)	0.0302 (2)	−0.00157 (15)	−0.00576 (15)	−0.00428 (15)
N1	0.043 (2)	0.058 (3)	0.053 (2)	0.002 (2)	−0.005 (2)	−0.026 (2)
N2	0.041 (2)	0.0344 (19)	0.0390 (18)	−0.0015 (15)	0.0078 (16)	−0.0037 (15)
N3	0.040 (2)	0.054 (2)	0.046 (2)	−0.0143 (17)	0.0170 (17)	−0.0082 (17)
N4	0.0329 (18)	0.0365 (19)	0.0305 (16)	−0.0079 (14)	0.0025 (14)	−0.0032 (14)
N5	0.0303 (17)	0.0407 (19)	0.0289 (16)	−0.0080 (14)	0.0045 (14)	0.0005 (14)
O1	0.0344 (16)	0.0520 (19)	0.0466 (17)	−0.0054 (14)	−0.0016 (13)	−0.0209 (14)
O2	0.0449 (17)	0.0512 (18)	0.0326 (15)	−0.0194 (14)	−0.0025 (13)	−0.0057 (13)
O3	0.0412 (18)	0.0306 (16)	0.075 (2)	−0.0001 (13)	−0.0259 (16)	0.0010 (14)
O4	0.0319 (16)	0.0437 (18)	0.0597 (19)	−0.0025 (13)	−0.0146 (14)	−0.0154 (14)
O5A	0.053 (5)	0.057 (6)	0.144 (11)	−0.016 (4)	0.002 (5)	−0.066 (6)
O6A	0.057 (5)	0.141 (12)	0.135 (12)	−0.011 (6)	0.030 (6)	−0.104 (9)
O5B	0.132 (14)	0.18 (3)	0.102 (14)	0.098 (16)	−0.080 (12)	−0.106 (16)
O6B	0.113 (17)	0.076 (11)	0.071 (9)	0.070 (11)	−0.042 (9)	−0.038 (7)
O7	0.0568 (19)	0.0482 (18)	0.0316 (15)	0.0068 (15)	0.0002 (14)	−0.0030 (13)
O8	0.0415 (17)	0.064 (2)	0.0260 (14)	−0.0082 (14)	0.0003 (12)	−0.0104 (13)
O9	0.089 (3)	0.054 (2)	0.0450 (18)	0.0212 (18)	−0.0100 (18)	−0.0207 (16)
O1W	0.0525 (19)	0.0505 (18)	0.0337 (15)	0.0112 (15)	−0.0013 (14)	0.0033 (13)
C1	0.0231 (19)	0.0286 (19)	0.0267 (18)	−0.0069 (15)	−0.0086 (14)	−0.0021 (15)
C2	0.039 (2)	0.0244 (19)	0.031 (2)	−0.0002 (16)	−0.0058 (16)	−0.0067 (15)
C3	0.026 (2)	0.033 (2)	0.038 (2)	0.0022 (16)	−0.0037 (16)	−0.0035 (17)
C4	0.030 (2)	0.030 (2)	0.033 (2)	−0.0053 (16)	−0.0054 (16)	0.0018 (16)
C5	0.037 (2)	0.029 (2)	0.030 (2)	−0.0003 (17)	0.0017 (17)	−0.0061 (16)
C6	0.0266 (19)	0.033 (2)	0.032 (2)	0.0005 (16)	−0.0016 (16)	−0.0022 (16)
C7	0.029 (2)	0.040 (2)	0.0271 (19)	−0.0014 (17)	−0.0017 (16)	0.0029 (17)
C8	0.033 (2)	0.033 (2)	0.0272 (19)	−0.0010 (16)	−0.0016 (16)	0.0055 (16)
C9	0.041 (2)	0.034 (2)	0.0272 (19)	−0.0109 (18)	−0.0037 (17)	0.0011 (16)
C10	0.039 (2)	0.032 (2)	0.0214 (18)	−0.0013 (17)	−0.0052 (16)	0.0018 (15)
C11	0.052 (3)	0.040 (2)	0.028 (2)	0.001 (2)	0.0000 (19)	−0.0025 (17)
C12	0.036 (2)	0.036 (2)	0.029 (2)	−0.0048 (17)	0.0026 (17)	−0.0021 (17)
C13	0.037 (2)	0.036 (2)	0.030 (2)	−0.0054 (17)	0.0083 (17)	−0.0068 (16)
C14	0.033 (2)	0.039 (2)	0.032 (2)	−0.0039 (17)	0.0027 (17)	0.0017 (17)
C15	0.033 (2)	0.050 (3)	0.029 (2)	−0.0076 (19)	0.0031 (17)	−0.0058 (18)
C16	0.045 (3)	0.045 (3)	0.037 (2)	0.000 (2)	−0.0007 (19)	−0.014 (2)
C17	0.048 (3)	0.039 (2)	0.040 (2)	0.006 (2)	−0.002 (2)	−0.0023 (19)
C18	0.069 (3)	0.053 (3)	0.047 (3)	0.017 (3)	−0.005 (2)	−0.002 (2)
C19	0.055 (3)	0.063 (3)	0.035 (2)	−0.008 (2)	0.006 (2)	−0.005 (2)
C20	0.109 (5)	0.063 (4)	0.077 (4)	0.034 (4)	−0.022 (4)	−0.028 (3)

Geometric parameters (Å, º)

As—O1	1.720 (3)	C1—C2	1.383 (5)
As—O2	1.664 (3)	C2—C3	1.371 (5)
As—O3	1.652 (3)	C2—H2	0.9300
As—C1	1.903 (3)	C3—C4	1.398 (5)
N1—O6B	1.113 (14)	C3—H3	0.9300
N1—O5A	1.181 (7)	C4—C5	1.391 (5)
N1—O6A	1.234 (11)	C5—C6	1.389 (5)
N1—O5B	1.268 (14)	C6—H6	0.9300
N1—C5	1.461 (5)	C7—C10	1.442 (5)
N2—C8	1.323 (5)	C9—C10	1.352 (5)
N2—H2A	0.9505	C9—H9	0.9300
N2—H2B	0.9591	C10—C11	1.500 (5)
N3—C7	1.336 (5)	C11—C12	1.518 (5)
N3—H3A	0.9238	C11—H11A	0.9700
N3—H3B	0.9225	C11—H11B	0.9700
N4—C7	1.334 (5)	C12—C13	1.380 (6)
N4—C8	1.337 (5)	C12—C17	1.390 (5)
N5—C9	1.352 (5)	C13—C14	1.396 (5)
N5—C8	1.353 (5)	C13—H13	0.9300
N5—H5A	0.9369	C14—C15	1.389 (6)
O1—H1	0.9332	C15—C16	1.382 (6)
O4—C4	1.339 (4)	C16—C17	1.382 (6)
O4—H4A	0.9169	C17—H17	0.9300
O7—C14	1.365 (5)	C18—H18A	0.9600
O7—C18	1.416 (5)	C18—H18B	0.9600
O8—C15	1.385 (5)	C18—H18C	0.9600
O8—C19	1.426 (5)	C19—H19A	0.9600
O9—C16	1.377 (5)	C19—H19B	0.9600
O9—C20	1.411 (6)	C19—H19C	0.9600
O1W—H1A	0.8608	C20—H20A	0.9600
O1W—H1B	0.8887	C20—H20B	0.9600
C1—C6	1.376 (5)	C20—H20C	0.9600
O1—As—C1	103.38 (14)	N2—C8—N5	118.1 (3)
O1—As—O2	108.51 (14)	N4—C8—N5	121.7 (3)
O1—As—O3	112.45 (15)	N5—C9—C10	122.4 (4)
O2—As—O3	113.01 (16)	N5—C9—H9	118.8
O2—As—C1	110.18 (14)	C10—C9—H9	118.8
O3—As—C1	108.88 (15)	C9—C10—C7	114.5 (3)
O5A—N1—O6A	121.3 (8)	C9—C10—C11	121.6 (4)
O6B—N1—O5B	120.3 (10)	C7—C10—C11	123.8 (4)
O6B—N1—C5	123.9 (9)	C10—C11—C12	119.4 (3)
O5A—N1—C5	120.6 (5)	C10—C11—H11A	107.5
O6A—N1—C5	117.3 (6)	C12—C11—H11A	107.5
O5B—N1—C5	115.1 (9)	C10—C11—H11B	107.5
C8—N2—H2A	118.4	C12—C11—H11B	107.5
C8—N2—H2B	120.5	H11A—C11—H11B	107.0
H2A—N2—H2B	116.9	C13—C12—C17	120.2 (4)
C7—N3—H3A	114.4	C13—C12—C11	124.0 (4)
C7—N3—H3B	120.0	C17—C12—C11	115.7 (4)
H3A—N3—H3B	124.4	C12—C13—C14	119.6 (4)
C7—N4—C8	118.4 (3)	C12—C13—H13	120.2
C9—N5—C8	119.8 (3)	C14—C13—H13	120.2
C9—N5—H5A	116.1	O7—C14—C15	114.8 (3)
C8—N5—H5A	123.9	O7—C14—C13	124.9 (4)
As—O1—H1	104.5	C15—C14—C13	120.2 (4)
C4—O4—H4A	112.1	C16—C15—O8	119.9 (4)
C14—O7—C18	117.7 (3)	C16—C15—C14	119.5 (4)
C15—O8—C19	113.0 (3)	O8—C15—C14	120.6 (4)
C16—O9—C20	118.8 (4)	O9—C16—C17	123.8 (4)
H1A—O1W—H1B	105.3	O9—C16—C15	115.7 (4)
C6—C1—C2	119.2 (3)	C17—C16—C15	120.5 (4)
C6—C1—As	117.3 (3)	C16—C17—C12	119.9 (4)
C2—C1—As	123.5 (3)	C16—C17—H17	120.1
C3—C2—C1	121.4 (3)	C12—C17—H17	120.1
C3—C2—H2	119.3	O7—C18—H18A	109.5
C1—C2—H2	119.3	O7—C18—H18B	109.5
C2—C3—C4	120.7 (3)	H18A—C18—H18B	109.5
C2—C3—H3	119.7	O7—C18—H18C	109.5
C4—C3—H3	119.7	H18A—C18—H18C	109.5
O4—C4—C5	120.6 (3)	H18B—C18—H18C	109.5
O4—C4—C3	122.3 (3)	O8—C19—H19A	109.5
C5—C4—C3	117.1 (3)	O8—C19—H19B	109.5
C6—C5—C4	122.2 (3)	H19A—C19—H19B	109.5
C6—C5—N1	116.4 (4)	O8—C19—H19C	109.5
C4—C5—N1	121.4 (3)	H19A—C19—H19C	109.5
C1—C6—C5	119.4 (3)	H19B—C19—H19C	109.5
C1—C6—H6	120.3	O9—C20—H20A	109.5
C5—C6—H6	120.3	O9—C20—H20B	109.5
N4—C7—N3	117.4 (4)	H20A—C20—H20B	109.5
N4—C7—C10	122.7 (3)	O9—C20—H20C	109.5
N3—C7—C10	119.9 (4)	H20A—C20—H20C	109.5
N2—C8—N4	120.2 (4)	H20B—C20—H20C	109.5
O3—As—C1—C6	49.6 (3)	C8—N5—C9—C10	4.0 (5)
O2—As—C1—C6	−74.8 (3)	N5—C9—C10—C7	1.8 (5)
O1—As—C1—C6	169.4 (3)	N5—C9—C10—C11	−175.1 (3)
O3—As—C1—C2	−131.2 (3)	N4—C7—C10—C9	−7.5 (5)
O2—As—C1—C2	104.3 (3)	N3—C7—C10—C9	173.7 (4)
O1—As—C1—C2	−11.5 (3)	N4—C7—C10—C11	169.3 (3)
C6—C1—C2—C3	0.3 (6)	N3—C7—C10—C11	−9.4 (6)
As—C1—C2—C3	−178.8 (3)	C9—C10—C11—C12	−99.1 (5)
C1—C2—C3—C4	−0.6 (6)	C7—C10—C11—C12	84.3 (5)
C2—C3—C4—O4	−179.2 (4)	C10—C11—C12—C13	−6.5 (6)
C2—C3—C4—C5	0.2 (6)	C10—C11—C12—C17	173.3 (4)
O4—C4—C5—C6	179.8 (4)	C17—C12—C13—C14	0.7 (6)
C3—C4—C5—C6	0.4 (6)	C11—C12—C13—C14	−179.5 (4)
O4—C4—C5—N1	0.5 (6)	C18—O7—C14—C15	−177.6 (4)
C3—C4—C5—N1	−178.9 (4)	C18—O7—C14—C13	2.9 (6)
O6B—N1—C5—C6	−29 (2)	C12—C13—C14—O7	179.1 (4)
O5A—N1—C5—C6	−149.4 (12)	C12—C13—C14—C15	−0.3 (6)
O6A—N1—C5—C6	21.1 (15)	C19—O8—C15—C16	97.4 (5)
O5B—N1—C5—C6	142 (2)	C19—O8—C15—C14	−84.5 (5)
O6B—N1—C5—C4	151 (2)	O7—C14—C15—C16	−179.4 (4)
O5A—N1—C5—C4	29.9 (13)	C13—C14—C15—C16	0.1 (6)
O6A—N1—C5—C4	−159.6 (14)	O7—C14—C15—O8	2.5 (5)
O5B—N1—C5—C4	−39 (2)	C13—C14—C15—O8	−178.0 (3)
C2—C1—C6—C5	0.3 (5)	C20—O9—C16—C17	4.3 (7)
As—C1—C6—C5	179.4 (3)	C20—O9—C16—C15	−176.7 (5)
C4—C5—C6—C1	−0.6 (6)	O8—C15—C16—O9	−1.1 (6)
N1—C5—C6—C1	178.7 (4)	C14—C15—C16—O9	−179.2 (4)
C8—N4—C7—N3	−174.2 (3)	O8—C15—C16—C17	177.9 (4)
C8—N4—C7—C10	7.0 (5)	C14—C15—C16—C17	−0.2 (6)
C7—N4—C8—N2	−178.9 (4)	O9—C16—C17—C12	179.5 (4)
C7—N4—C8—N5	−0.7 (5)	C15—C16—C17—C12	0.6 (7)
C9—N5—C8—N2	173.5 (3)	C13—C12—C17—C16	−0.8 (6)
C9—N5—C8—N4	−4.8 (5)	C11—C12—C17—C16	179.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.95	1.87	2.817 (4)	176
N2—H2B···N4^i	0.96	2.48	3.318 (5)	146
N3—H3A···O7^ii	0.92	2.51	3.223 (4)	135
N3—H3B···O4^iii	0.92	2.33	3.139 (5)	147
N3—H3B···O5A^iii	0.92	2.48	3.078 (10)	123
N5—H5A···O3^i	0.94	1.70	2.607 (5)	162
O1—H1···O2^iv	0.93	1.67	2.582 (4)	165
O4—H4A···O1W	0.92	1.65	2.545 (4)	165
O1W—H1A···O2^v	0.86	1.83	2.687 (4)	171
O1W—H1B···O8^vi	0.89	2.46	3.221 (4)	143
O1W—H1B···O9^vi	0.89	2.01	2.767 (4)	142

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