N,N-Diethyl-2-hy-droxy-ethanaminium 5-(2,4-di-nitro-phen-yl)barbiturate sesquihydrate.

In the title hydrated mol-ecular salt, C6H16NO(+)·C10H5N4O7 (-)·1.5H2O [systematic name: N,N-diethyl-2-hy-droxy-ethan-am-in-ium 5-(2,4-di-nitro-phen-yl)-2,6-di-oxo-1,2,3,6-tetra-hydro-pyrim-idin-4-olate sesquihydrate], the dihedral angle between the six-membered rings in the anion is 37.66 (11)°. The nitro groups ortho and para to the ring junction are rotated from their attached ring by 40.8 (3) and 23.5 (3)°, respectively. The ethanol group is disordered over two of the 'arms' of the cation in a statistical ratio. In the crystal, [010] chains of anions occur, linked by N-H⋯O and O-H⋯O hydrogen bonds, which generate R 2 (2)(8) loops. Further N-H⋯O and O-H⋯O hydrogen bonds link the components into a three-dimensional network. One of the water O atoms lies near an inversion centre and is 50% occupied.

Related literature

For related barbiturates, see: Kalaivani et al. (2008 ▶); Kalaivani & Buvaneswari (2010 ▶); Buvaneswari & Kalaivani (2011 ▶); Babykala & Kalaivani (2012 ▶).

Experimental

Crystal data

C6H16NO+·C10H5N4O7 −·1.5H2O

M = 438.40

Monoclinic,

a = 9.6003 (5) Å

b = 11.6568 (6) Å

c = 18.1993 (9) Å

β = 98.066 (3)°

V = 2016.51 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004) ▶ T min = 0.948, T max = 0.979

16207 measured reflections

3219 independent reflections

2353 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.09

3219 reflections

341 parameters

49 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (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, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012257/hb7074sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012257/hb7074Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012257/hb7074Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H16NO+·C10H5N4O7−·1.5H2O	F(000) = 924
Mr = 438.40	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6003 (5) Å	Cell parameters from 5746 reflections
b = 11.6568 (6) Å	θ = 2.1–24.1°
c = 18.1993 (9) Å	µ = 0.12 mm−1
β = 98.066 (3)°	T = 293 K
V = 2016.51 (18) Å3	Block, red
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3219 independent reflections
Radiation source: fine-focus sealed tube	2353 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scan	θmax = 24.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→10
Tmin = 0.948, Tmax = 0.979	k = −13→13
16207 measured reflections	l = −20→20

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0518P)2 + 1.3181P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3219 reflections	Δρmax = 0.34 e Å−3
341 parameters	Δρmin = −0.26 e Å−3
49 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: 0.0070 (12)

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	Occ. (<1)
C1	0.2628 (2)	0.0366 (2)	0.54157 (13)	0.0329 (6)
C2	0.2250 (3)	0.0267 (2)	0.46611 (13)	0.0391 (6)
H2	0.1497	−0.0193	0.4465	0.047*
C3	0.3010 (3)	0.0862 (2)	0.42078 (13)	0.0382 (6)
C4	0.4145 (3)	0.1532 (2)	0.44884 (13)	0.0392 (6)
H4	0.4629	0.1959	0.4174	0.047*
C5	0.4544 (3)	0.1556 (2)	0.52411 (13)	0.0356 (6)
H5	0.5339	0.1975	0.5429	0.043*
C6	0.3811 (2)	0.09788 (18)	0.57400 (12)	0.0302 (5)
C7	0.4339 (2)	0.09933 (19)	0.65315 (12)	0.0307 (5)
C8	0.4299 (2)	−0.0016 (2)	0.69591 (12)	0.0320 (5)
C9	0.5512 (3)	0.0971 (2)	0.80407 (13)	0.0415 (6)
C10	0.4982 (2)	0.1991 (2)	0.68671 (12)	0.0333 (6)
C11	0.055 (3)	0.421 (2)	0.6323 (12)	0.123 (6)	0.50
H11A	0.0931	0.4283	0.6844	0.148*	0.50
H11B	0.0582	0.4964	0.6100	0.148*	0.50
C12	0.148 (2)	0.341 (2)	0.5957 (12)	0.123 (6)	0.50
H12A	0.2171	0.3879	0.5757	0.148*	0.50
H12B	0.1987	0.2941	0.6346	0.148*	0.50
O8	0.0978 (6)	0.2768 (6)	0.5468 (3)	0.0968 (18)	0.50
H8	0.0804	0.3126	0.5078	0.145*	0.50
C11'	0.0599 (11)	0.4204 (8)	0.6337 (5)	0.0340 (19)	0.50
H11C	0.0687	0.4851	0.6012	0.041*	0.50
H11D	0.0916	0.4447	0.6842	0.041*	0.50
C12'	0.1500 (14)	0.3260 (12)	0.6142 (7)	0.058 (2)	0.50
H12C	0.1463	0.2636	0.6483	0.087*	0.50
H12D	0.2452	0.3526	0.6169	0.087*	0.50
H12E	0.1173	0.3002	0.5647	0.087*	0.50
C13	−0.1176 (4)	0.2726 (3)	0.66133 (19)	0.0675 (9)
H13A	−0.0693	0.2132	0.6374	0.081*
H13B	−0.2176	0.2562	0.6517	0.081*
C14	−0.0709 (5)	0.2668 (4)	0.7436 (2)	0.0950 (13)
H14A	0.0297	0.2732	0.7535	0.142*
H14B	−0.0996	0.1948	0.7624	0.142*
H14C	−0.1130	0.3285	0.7676	0.142*
C15	−0.169 (2)	0.4779 (19)	0.6581 (13)	0.125 (6)	0.50
H15A	−0.1266	0.4882	0.7093	0.149*	0.50
H15B	−0.2639	0.4505	0.6590	0.149*	0.50
C16	−0.179 (3)	0.5919 (19)	0.6233 (11)	0.120 (6)	0.50
H16A	−0.2529	0.6364	0.6412	0.144*	0.50
H16B	−0.0910	0.6330	0.6347	0.144*	0.50
O9	−0.2118 (8)	0.5734 (6)	0.5442 (3)	0.109 (2)	0.50
H9	−0.2877	0.5405	0.5351	0.164*	0.50
C15'	−0.1878 (13)	0.4742 (14)	0.6532 (12)	0.073 (4)	0.50
H15C	−0.2805	0.4412	0.6536	0.088*	0.50
H15D	−0.1517	0.4977	0.7034	0.088*	0.50
C16'	−0.198 (2)	0.5752 (15)	0.6036 (11)	0.104 (6)	0.50
H16C	−0.1060	0.5972	0.5945	0.156*	0.50
H16D	−0.2409	0.6376	0.6267	0.156*	0.50
H16E	−0.2550	0.5563	0.5575	0.156*	0.50
N1	0.2581 (2)	0.0802 (2)	0.34106 (12)	0.0495 (6)
N2	0.1609 (2)	−0.01230 (19)	0.58625 (12)	0.0427 (5)
N3	0.4909 (2)	0.00326 (16)	0.76952 (10)	0.0392 (5)
H3	0.4902	−0.0585	0.7953	0.047*
N4	0.5523 (2)	0.19167 (17)	0.76131 (10)	0.0397 (5)
H4A	0.5898	0.2526	0.7822	0.048*
N5	−0.0911 (3)	0.3855 (2)	0.62698 (15)	0.0531 (6)
O1	0.37759 (18)	−0.09499 (13)	0.67247 (9)	0.0400 (4)
O2	0.5996 (3)	0.09640 (17)	0.87033 (10)	0.0673 (7)
O3	0.50875 (19)	0.29377 (14)	0.65590 (9)	0.0432 (5)
O4	0.2933 (2)	0.1579 (2)	0.30267 (10)	0.0642 (6)
O5	0.1890 (3)	−0.0026 (2)	0.31603 (11)	0.0756 (7)
O6	0.1012 (2)	−0.10192 (18)	0.56472 (12)	0.0613 (6)
O7	0.1327 (2)	0.04142 (17)	0.63940 (11)	0.0542 (5)
O10	0.7928 (4)	0.1814 (3)	0.98317 (18)	0.1345 (15)
O11	0.5047 (15)	−0.0413 (8)	0.9782 (6)	0.193 (5)	0.50
H5A	−0.126 (4)	0.376 (3)	0.574 (2)	0.079 (10)*
H10B	0.744 (5)	0.145 (4)	0.944 (2)	0.16 (2)*
H10A	0.818 (6)	0.251 (3)	0.969 (3)	0.19 (3)*

	U11	U22	U33	U12	U13	U23
C1	0.0335 (13)	0.0302 (13)	0.0342 (13)	0.0035 (11)	0.0017 (10)	−0.0016 (10)
C2	0.0345 (13)	0.0388 (14)	0.0408 (14)	0.0048 (11)	−0.0057 (11)	−0.0061 (11)
C3	0.0418 (14)	0.0416 (15)	0.0289 (13)	0.0114 (12)	−0.0029 (11)	−0.0019 (11)
C4	0.0476 (15)	0.0373 (14)	0.0327 (14)	0.0037 (12)	0.0061 (12)	0.0011 (11)
C5	0.0407 (14)	0.0325 (13)	0.0325 (13)	−0.0009 (11)	0.0009 (11)	−0.0012 (11)
C6	0.0355 (13)	0.0228 (12)	0.0313 (12)	0.0077 (10)	0.0013 (10)	−0.0021 (10)
C7	0.0376 (13)	0.0249 (12)	0.0286 (12)	0.0022 (10)	0.0015 (10)	−0.0013 (10)
C8	0.0364 (13)	0.0295 (13)	0.0295 (12)	0.0028 (11)	0.0024 (10)	−0.0023 (10)
C9	0.0589 (17)	0.0327 (14)	0.0303 (14)	0.0006 (13)	−0.0032 (12)	−0.0019 (11)
C10	0.0402 (14)	0.0280 (13)	0.0314 (13)	0.0021 (11)	0.0042 (11)	−0.0022 (10)
C11	0.117 (12)	0.123 (13)	0.123 (13)	−0.008 (10)	−0.003 (10)	0.002 (10)
C12	0.108 (11)	0.119 (12)	0.136 (12)	0.011 (8)	−0.005 (9)	−0.008 (9)
O8	0.089 (4)	0.126 (5)	0.073 (3)	0.028 (3)	0.004 (3)	−0.028 (3)
C11'	0.035 (4)	0.034 (4)	0.030 (4)	−0.007 (4)	−0.003 (3)	0.000 (3)
C12'	0.039 (4)	0.069 (6)	0.062 (5)	0.011 (4)	−0.004 (4)	0.002 (4)
C13	0.066 (2)	0.058 (2)	0.075 (2)	−0.0106 (16)	−0.0018 (17)	0.0037 (17)
C14	0.111 (3)	0.090 (3)	0.077 (3)	−0.028 (2)	−0.008 (2)	0.026 (2)
C15	0.193 (13)	0.101 (11)	0.076 (9)	0.043 (10)	0.007 (9)	−0.014 (8)
C16	0.189 (12)	0.085 (10)	0.079 (7)	0.042 (8)	−0.002 (7)	−0.018 (6)
O9	0.161 (7)	0.092 (4)	0.070 (4)	0.037 (4)	−0.001 (4)	0.002 (4)
C15'	0.055 (5)	0.061 (7)	0.110 (11)	0.024 (5)	0.037 (5)	−0.004 (7)
C16'	0.104 (8)	0.058 (7)	0.151 (17)	0.039 (6)	0.019 (10)	−0.007 (10)
N1	0.0520 (14)	0.0595 (16)	0.0343 (13)	0.0112 (13)	−0.0036 (11)	−0.0041 (12)
N2	0.0382 (12)	0.0411 (13)	0.0472 (13)	0.0017 (11)	0.0006 (10)	0.0016 (11)
N3	0.0602 (14)	0.0265 (11)	0.0284 (11)	−0.0010 (10)	−0.0029 (9)	0.0030 (9)
N4	0.0573 (14)	0.0272 (11)	0.0312 (11)	−0.0047 (10)	−0.0051 (10)	−0.0048 (9)
N5	0.0562 (16)	0.0510 (15)	0.0500 (15)	0.0065 (12)	0.0001 (12)	−0.0067 (12)
O1	0.0543 (11)	0.0248 (9)	0.0376 (10)	−0.0029 (8)	−0.0053 (8)	−0.0010 (7)
O2	0.1120 (18)	0.0475 (12)	0.0334 (11)	−0.0130 (12)	−0.0207 (11)	0.0022 (9)
O3	0.0687 (12)	0.0263 (9)	0.0327 (9)	−0.0060 (8)	0.0009 (8)	0.0006 (7)
O4	0.0747 (15)	0.0790 (16)	0.0362 (11)	0.0055 (12)	−0.0016 (10)	0.0101 (11)
O5	0.0957 (18)	0.0804 (16)	0.0435 (12)	−0.0150 (14)	−0.0150 (11)	−0.0126 (11)
O6	0.0528 (12)	0.0529 (13)	0.0769 (15)	−0.0191 (10)	0.0051 (10)	−0.0075 (11)
O7	0.0551 (12)	0.0581 (13)	0.0524 (12)	0.0048 (10)	0.0185 (9)	−0.0030 (10)
O10	0.173 (3)	0.106 (2)	0.097 (2)	−0.064 (2)	−0.076 (2)	0.0379 (19)
O11	0.262 (11)	0.162 (11)	0.153 (10)	−0.096 (10)	0.021 (9)	0.020 (6)

C1—C2	1.375 (3)	C12'—H12D	0.9600
C1—C6	1.400 (3)	C12'—H12E	0.9600
C1—N2	1.472 (3)	C13—N5	1.495 (4)
C2—C3	1.366 (4)	C13—C14	1.504 (5)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.379 (4)	C13—H13B	0.9700
C3—N1	1.453 (3)	C14—H14A	0.9600
C4—C5	1.370 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.397 (3)	C15—N5	1.47 (2)
C5—H5	0.9300	C15—C16	1.470 (13)
C6—C7	1.458 (3)	C15—H15A	0.9700
C7—C8	1.414 (3)	C15—H15B	0.9700
C7—C10	1.415 (3)	C16—O9	1.44 (2)
C8—O1	1.248 (3)	C16—H16A	0.9700
C8—N3	1.386 (3)	C16—H16B	0.9700
C9—O2	1.230 (3)	O9—H9	0.8200
C9—N4	1.350 (3)	C15'—C16'	1.478 (12)
C9—N3	1.351 (3)	C15'—N5	1.512 (15)
C10—O3	1.248 (3)	C15'—H15C	0.9700
C10—N4	1.387 (3)	C15'—H15D	0.9700
C11—N5	1.45 (2)	C16'—H16C	0.9600
C11—C12	1.509 (13)	C16'—H16D	0.9600
C11—H11A	0.9700	C16'—H16E	0.9600
C11—H11B	0.9700	N1—O4	1.220 (3)
C12—O8	1.21 (2)	N1—O5	1.223 (3)
C12—H12A	0.9700	N2—O7	1.214 (3)
C12—H12B	0.9700	N2—O6	1.229 (3)
O8—H8	0.8200	N3—H3	0.8600
C11'—C12'	1.474 (10)	N4—H4A	0.8600
C11'—N5	1.493 (11)	N5—H5A	0.97 (4)
C11'—H11C	0.9700	O10—H10B	0.903 (19)
C11'—H11D	0.9700	O10—H10A	0.89 (2)
C12'—H12C	0.9600	O11—O11i	1.260 (18)
C2—C1—C6	123.3 (2)	H13A—C13—H13B	107.6
C2—C1—N2	114.6 (2)	C13—C14—H14A	109.5
C6—C1—N2	121.8 (2)	C13—C14—H14B	109.5
C3—C2—C1	118.2 (2)	H14A—C14—H14B	109.5
C3—C2—H2	120.9	C13—C14—H14C	109.5
C1—C2—H2	120.9	H14A—C14—H14C	109.5
C2—C3—C4	121.7 (2)	H14B—C14—H14C	109.5
C2—C3—N1	118.5 (2)	N5—C15—C16	120.3 (17)
C4—C3—N1	119.7 (2)	N5—C15—H15A	107.2
C5—C4—C3	118.5 (2)	C16—C15—H15A	107.2
C5—C4—H4	120.8	N5—C15—H15B	107.2
C3—C4—H4	120.8	C16—C15—H15B	107.2
C4—C5—C6	123.0 (2)	H15A—C15—H15B	106.9
C4—C5—H5	118.5	O9—C16—C15	106.7 (16)
C6—C5—H5	118.5	O9—C16—H16A	110.4
C5—C6—C1	115.1 (2)	C15—C16—H16A	110.4
C5—C6—C7	120.0 (2)	O9—C16—H16B	110.4
C1—C6—C7	124.8 (2)	C15—C16—H16B	110.4
C8—C7—C10	119.4 (2)	H16A—C16—H16B	108.6
C8—C7—C6	120.1 (2)	C16—O9—H9	109.5
C10—C7—C6	120.4 (2)	C16'—C15'—N5	110.1 (12)
O1—C8—N3	117.5 (2)	C16'—C15'—H15C	109.6
O1—C8—C7	125.3 (2)	N5—C15'—H15C	109.6
N3—C8—C7	117.2 (2)	C16'—C15'—H15D	109.6
O2—C9—N4	122.5 (2)	N5—C15'—H15D	109.6
O2—C9—N3	122.0 (2)	H15C—C15'—H15D	108.2
N4—C9—N3	115.5 (2)	C15'—C16'—H16C	109.5
O3—C10—N4	116.9 (2)	C15'—C16'—H16D	109.5
O3—C10—C7	126.2 (2)	H16C—C16'—H16D	109.5
N4—C10—C7	116.9 (2)	C15'—C16'—H16E	109.5
N5—C11—C12	114.7 (18)	H16C—C16'—H16E	109.5
N5—C11—H11A	108.6	H16D—C16'—H16E	109.5
C12—C11—H11A	108.6	O4—N1—O5	123.5 (2)
N5—C11—H11B	108.6	O4—N1—C3	118.3 (2)
C12—C11—H11B	108.6	O5—N1—C3	118.2 (2)
H11A—C11—H11B	107.6	O7—N2—O6	123.1 (2)
O8—C12—C11	121 (2)	O7—N2—C1	118.7 (2)
O8—C12—H12A	107.2	O6—N2—C1	118.0 (2)
C11—C12—H12A	107.2	C9—N3—C8	125.4 (2)
O8—C12—H12B	107.2	C9—N3—H3	117.3
C11—C12—H12B	107.2	C8—N3—H3	117.3
H12A—C12—H12B	106.8	C9—N4—C10	125.7 (2)
C12—O8—H8	109.5	C9—N4—H4A	117.2
C12'—C11'—N5	111.9 (9)	C10—N4—H4A	117.2
C12'—C11'—H11C	109.2	C11—N5—C15	107.6 (13)
N5—C11'—H11C	109.2	C11—N5—C11'	1.2 (13)
C12'—C11'—H11D	109.2	C15—N5—C11'	108.0 (10)
N5—C11'—H11D	109.2	C11—N5—C13	116.3 (10)
H11C—C11'—H11D	107.9	C15—N5—C13	111.0 (9)
C11'—C12'—H12C	109.5	C11'—N5—C13	115.2 (4)
C11'—C12'—H12D	109.5	C11—N5—C15'	114.4 (11)
H12C—C12'—H12D	109.5	C15—N5—C15'	7.4 (15)
C11'—C12'—H12E	109.5	C11'—N5—C15'	114.9 (7)
H12C—C12'—H12E	109.5	C13—N5—C15'	108.8 (6)
H12D—C12'—H12E	109.5	C11—N5—H5A	107 (2)
N5—C13—C14	114.3 (3)	C15—N5—H5A	110 (2)
N5—C13—H13A	108.7	C11'—N5—H5A	108 (2)
C14—C13—H13A	108.7	C13—N5—H5A	105 (2)
N5—C13—H13B	108.7	C15'—N5—H5A	104 (2)
C14—C13—H13B	108.7	H10B—O10—H10A	109 (3)
C6—C1—C2—C3	−4.7 (4)	C6—C1—N2—O7	37.2 (3)
N2—C1—C2—C3	169.2 (2)	C2—C1—N2—O6	38.1 (3)
C1—C2—C3—C4	1.2 (4)	C6—C1—N2—O6	−147.8 (2)
C1—C2—C3—N1	−177.4 (2)	O2—C9—N3—C8	177.7 (3)
C2—C3—C4—C5	2.7 (4)	N4—C9—N3—C8	−1.1 (4)
N1—C3—C4—C5	−178.7 (2)	O1—C8—N3—C9	−179.5 (2)
C3—C4—C5—C6	−3.4 (4)	C7—C8—N3—C9	1.3 (4)
C4—C5—C6—C1	0.1 (3)	O2—C9—N4—C10	−179.1 (3)
C4—C5—C6—C7	176.8 (2)	N3—C9—N4—C10	−0.3 (4)
C2—C1—C6—C5	4.1 (3)	O3—C10—N4—C9	−179.9 (2)
N2—C1—C6—C5	−169.4 (2)	C7—C10—N4—C9	1.4 (4)
C2—C1—C6—C7	−172.5 (2)	C12—C11—N5—C15	−174.2 (17)
N2—C1—C6—C7	14.1 (3)	C12—C11—N5—C11'	76 (62)
C5—C6—C7—C8	−138.6 (2)	C12—C11—N5—C13	60.6 (19)
C1—C6—C7—C8	37.7 (3)	C12—C11—N5—C15'	−171.2 (15)
C5—C6—C7—C10	36.9 (3)	C16—C15—N5—C11	63 (2)
C1—C6—C7—C10	−146.7 (2)	C16—C15—N5—C11'	64 (2)
C10—C7—C8—O1	−179.2 (2)	C16—C15—N5—C13	−168.7 (16)
C6—C7—C8—O1	−3.6 (4)	C16—C15—N5—C15'	−95 (12)
C10—C7—C8—N3	−0.1 (3)	C12'—C11'—N5—C11	−118 (62)
C6—C7—C8—N3	175.5 (2)	C12'—C11'—N5—C15	171.4 (11)
C8—C7—C10—O3	−179.7 (2)	C12'—C11'—N5—C13	46.7 (8)
C6—C7—C10—O3	4.7 (4)	C12'—C11'—N5—C15'	174.3 (10)
C8—C7—C10—N4	−1.1 (3)	C14—C13—N5—C11	61.7 (10)
C6—C7—C10—N4	−176.7 (2)	C14—C13—N5—C15	−61.7 (11)
N5—C11—C12—O8	23 (3)	C14—C13—N5—C11'	61.4 (5)
N5—C15—C16—O9	45 (3)	C14—C13—N5—C15'	−69.2 (9)
C2—C3—N1—O4	156.9 (2)	C16'—C15'—N5—C11	66.1 (17)
C4—C3—N1—O4	−21.7 (3)	C16'—C15'—N5—C15	89 (11)
C2—C3—N1—O5	−23.3 (3)	C16'—C15'—N5—C11'	67.3 (14)
C4—C3—N1—O5	158.1 (2)	C16'—C15'—N5—C13	−161.9 (10)
C2—C1—N2—O7	−136.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O9ii	0.82	2.14	2.739 (10)	130
O9—H9···O11iii	0.82	2.11	2.841 (17)	148
N3—H3···O3iv	0.86	1.94	2.794 (2)	174
N4—H4A···O1v	0.86	1.97	2.804 (3)	165
N5—H5A···O10iii	0.97 (4)	1.86 (4)	2.808 (4)	164 (3)
O10—H10B···O2	0.90 (2)	1.87 (3)	2.751 (3)	163 (5)
O10—H10A···O6v	0.89 (2)	2.02 (2)	2.902 (4)	172 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O9i	0.82	2.14	2.739 (10)	130
O9—H9⋯O11ii	0.82	2.11	2.841 (17)	148
N3—H3⋯O3iii	0.86	1.94	2.794 (2)	174
N4—H4A⋯O1iv	0.86	1.97	2.804 (3)	165
N5—H5A⋯O10ii	0.97 (4)	1.86 (4)	2.808 (4)	164 (3)
O10—H10B⋯O2	0.90 (2)	1.87 (3)	2.751 (3)	163 (5)
O10—H10A⋯O6iv	0.89 (2)	2.02 (2)	2.902 (4)	172 (6)

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