Ethane-1,2-diaminium 3,4,5,6-tetra-bromo-2-(methoxy-carbon-yl)benzoate methanol solvate.

In the title compound, C(2)H(10)N(2) (2+)·2C(9)H(3)Br(4)O(4) (-)·CH(4)O, the N atoms of the ethane-1,2-diamine mol-ecule are protonated. The crystal structure is stabilized by N-H⋯O hydrogen bonds between the ethane-1,2-diaminium cations and 3,4,5,6-tetra-bromo-2-(methoxy-carbon-yl)bromo-benzoate anions, and by O-H⋯O and N-H⋯O hydrogen bonds between the methanol solvate and both the cation and the anion. In addition, the crystal structure exhibits a C-Br⋯O halogen bond [3.20 (3) Å] and a Br⋯Br inter-action [3.560 (2) Å].

Related literature

For related structures, see: Liang et al. (2006 ▶, 2007 ▶); For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C2H10N2 2+·2C9H3Br4O4 −·CH4O

M = 1083.67

Monoclinic,

a = 6.456 (2) Å

b = 19.036 (7) Å

c = 26.017 (9) Å

β = 96.002 (6)°

V = 3179.7 (19) Å3

Z = 4

Mo Kα radiation

μ = 10.14 mm−1

T = 298 (2) K

0.41 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.062, T max = 0.221

15827 measured reflections

5585 independent reflections

3448 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.145

S = 0.98

5585 reflections

367 parameters

6 restraints

H-atom parameters constrained

Δρmax = 1.18 e Å−3

Δρmin = −0.72 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038166/lx2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038166/lx2065Isup2.hkl

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

C2H10N22+·2C9H3Br4O4–·CH4O	F000 = 2048
Mr = 1083.67	Dx = 2.264 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2716 reflections
a = 6.456 (2) Å	θ = 2.3–22.1º
b = 19.036 (7) Å	µ = 10.14 mm−1
c = 26.017 (9) Å	T = 298 (2) K
β = 96.002 (6)º	Block, colourless
V = 3179.7 (19) Å3	0.41 × 0.25 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5585 independent reflections
Radiation source: fine-focus sealed tube	3448 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.083
Detector resolution: 10.0 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 1.6º
φ and ω scans	h = −7→6
Absorption correction: multi-scan(SADABS; Bruker, 1997)	k = −22→22
Tmin = 0.062, Tmax = 0.221	l = −30→25
15827 measured reflections

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
5585 reflections	Δρmax = 1.18 e Å−3
367 parameters	Δρmin = −0.72 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C13	0.2706 (12)	0.7587 (4)	0.4305 (3)	0.028 (2)
Br5	0.90144 (14)	0.74383 (5)	0.53528 (4)	0.0387 (3)
Br8	0.01592 (15)	0.76205 (5)	0.38806 (4)	0.0515 (3)
Br7	0.18589 (16)	0.89882 (5)	0.45626 (4)	0.0508 (3)
Br1	1.30682 (16)	1.00363 (5)	0.23756 (4)	0.0488 (3)
Br6	0.64413 (16)	0.89277 (5)	0.52383 (4)	0.0473 (3)
Br3	0.7771 (2)	1.01282 (6)	0.39936 (4)	0.0712 (4)
Br4	0.52006 (19)	0.87733 (7)	0.34731 (5)	0.0694 (4)
Br2	1.1722 (2)	1.07590 (7)	0.34433 (5)	0.0789 (4)
O5	0.7309 (8)	0.5905 (3)	0.5074 (2)	0.0316 (14)
O6	0.7401 (9)	0.6008 (3)	0.4220 (2)	0.0355 (15)
O2	0.9487 (9)	0.9138 (3)	0.1572 (2)	0.0366 (15)
O9	0.2812 (10)	0.7719 (3)	0.1141 (2)	0.0387 (15)
H9	0.2528	0.7917	0.1405	0.058*
C15	0.5347 (13)	0.8125 (4)	0.4890 (3)	0.029 (2)
N1	0.9242 (10)	0.4714 (3)	0.4311 (2)	0.0295 (17)
H1A	0.9667	0.4597	0.4008	0.044*
H1B	1.0283	0.4655	0.4559	0.044*
H1C	0.8841	0.5161	0.4303	0.044*
C14	0.3451 (13)	0.8158 (4)	0.4590 (3)	0.027 (2)
C4	0.7531 (14)	0.9129 (5)	0.3182 (3)	0.040 (2)
C5	0.8078 (13)	0.8814 (4)	0.2718 (3)	0.031 (2)
C11	0.3057 (13)	0.6319 (5)	0.4029 (3)	0.031 (2)
O1	1.1336 (11)	0.8281 (3)	0.1981 (2)	0.0498 (18)
C16	0.6458 (12)	0.7499 (4)	0.4910 (3)	0.0247 (18)
C19	0.5754 (12)	0.4323 (4)	0.3977 (3)	0.029 (2)
H19A	0.5067	0.4775	0.3995	0.035*
H19B	0.6339	0.4295	0.3649	0.035*
C17	0.5723 (12)	0.6915 (4)	0.4644 (3)	0.0234 (19)
N2	0.4214 (10)	0.3748 (3)	0.4012 (2)	0.0307 (17)
H2A	0.4809	0.3337	0.3956	0.046*
H2B	0.3132	0.3815	0.3776	0.046*
H2C	0.3779	0.3748	0.4326	0.046*
O4	0.7137 (11)	0.7667 (3)	0.2822 (3)	0.059 (2)
C18	0.6933 (12)	0.6221 (4)	0.4644 (3)	0.0236 (19)
O3	0.6344 (11)	0.8134 (4)	0.2056 (3)	0.061 (2)
C1	1.0757 (13)	0.9683 (5)	0.2702 (3)	0.034 (2)
C6	0.9726 (13)	0.9107 (4)	0.2478 (3)	0.0260 (19)
C12	0.3863 (12)	0.6964 (4)	0.4321 (3)	0.0212 (18)
C7	1.0268 (14)	0.8808 (5)	0.1962 (3)	0.030 (2)
O7	0.2565 (9)	0.5792 (3)	0.4236 (2)	0.0381 (15)
O8	0.2970 (10)	0.6420 (3)	0.3525 (2)	0.0475 (17)
C8	0.7027 (14)	0.8161 (5)	0.2485 (4)	0.039 (2)
C2	1.0236 (15)	0.9986 (5)	0.3156 (3)	0.039 (2)
C3	0.8613 (17)	0.9711 (5)	0.3390 (4)	0.046 (3)
C20	0.7472 (12)	0.4262 (4)	0.4415 (3)	0.029 (2)
H20A	0.6956	0.4404	0.4736	0.035*
H20B	0.7929	0.3777	0.4450	0.035*
C21	0.3236 (18)	0.7007 (5)	0.1248 (4)	0.059 (3)
H21A	0.4547	0.6966	0.1457	0.089*
H21B	0.3300	0.6757	0.0930	0.089*
H21C	0.2153	0.6813	0.1431	0.089*
C10	0.192 (2)	0.5888 (6)	0.3205 (4)	0.077 (4)
H10A	0.2580	0.5442	0.3279	0.116*
H10B	0.1982	0.6004	0.2848	0.116*
H10C	0.0488	0.5861	0.3274	0.116*
C9	0.605 (3)	0.7038 (7)	0.2652 (5)	0.112 (6)
H9A	0.4793	0.7160	0.2440	0.169*
H9B	0.5708	0.6776	0.2946	0.169*
H9C	0.6919	0.6759	0.2455	0.169*

	U11	U22	U33	U12	U13	U23
C13	0.026 (5)	0.040 (5)	0.017 (4)	0.004 (4)	−0.001 (3)	0.010 (4)
Br5	0.0371 (5)	0.0371 (6)	0.0384 (6)	−0.0028 (4)	−0.0124 (4)	−0.0011 (4)
Br8	0.0390 (6)	0.0536 (7)	0.0570 (7)	0.0077 (5)	−0.0170 (5)	0.0117 (5)
Br7	0.0594 (7)	0.0334 (6)	0.0609 (7)	0.0211 (5)	0.0124 (5)	0.0069 (5)
Br1	0.0489 (6)	0.0493 (6)	0.0484 (7)	−0.0134 (5)	0.0065 (5)	−0.0022 (5)
Br6	0.0684 (7)	0.0281 (5)	0.0453 (6)	−0.0054 (5)	0.0055 (5)	−0.0119 (5)
Br3	0.1170 (11)	0.0641 (8)	0.0366 (6)	0.0414 (7)	0.0267 (6)	0.0001 (6)
Br4	0.0671 (8)	0.0844 (9)	0.0636 (8)	0.0141 (6)	0.0398 (6)	0.0286 (7)
Br2	0.1045 (11)	0.0677 (8)	0.0625 (8)	−0.0110 (7)	−0.0005 (7)	−0.0366 (7)
O5	0.038 (4)	0.032 (3)	0.025 (3)	0.006 (3)	0.003 (3)	0.004 (3)
O6	0.050 (4)	0.026 (3)	0.032 (4)	0.010 (3)	0.011 (3)	−0.001 (3)
O2	0.046 (4)	0.047 (4)	0.017 (3)	−0.008 (3)	0.003 (3)	0.009 (3)
O9	0.053 (4)	0.026 (3)	0.036 (4)	−0.003 (3)	0.005 (3)	−0.002 (3)
C15	0.044 (6)	0.022 (5)	0.023 (5)	0.004 (4)	0.008 (4)	0.000 (4)
N1	0.037 (4)	0.029 (4)	0.023 (4)	0.005 (3)	0.007 (3)	−0.004 (3)
C14	0.034 (5)	0.023 (5)	0.023 (5)	0.011 (4)	0.008 (4)	0.005 (4)
C4	0.037 (6)	0.059 (7)	0.027 (5)	0.022 (5)	0.012 (4)	0.023 (5)
C5	0.033 (5)	0.041 (6)	0.021 (5)	0.008 (4)	0.006 (4)	0.013 (4)
C11	0.034 (5)	0.037 (6)	0.023 (5)	−0.002 (4)	−0.001 (4)	0.001 (4)
O1	0.065 (5)	0.046 (4)	0.039 (4)	0.025 (4)	0.006 (3)	−0.006 (3)
C16	0.028 (4)	0.028 (5)	0.017 (4)	0.000 (4)	0.001 (3)	0.003 (4)
C19	0.037 (5)	0.021 (5)	0.030 (5)	0.001 (4)	0.005 (4)	0.006 (4)
C17	0.027 (5)	0.021 (5)	0.023 (5)	0.003 (3)	0.006 (4)	0.001 (4)
N2	0.033 (4)	0.035 (4)	0.022 (4)	0.000 (3)	−0.003 (3)	0.001 (3)
O4	0.078 (5)	0.043 (4)	0.055 (5)	−0.021 (4)	0.000 (4)	0.012 (4)
C18	0.022 (4)	0.022 (5)	0.026 (5)	−0.002 (3)	−0.002 (4)	0.000 (4)
O3	0.061 (5)	0.083 (6)	0.038 (4)	−0.036 (4)	0.002 (4)	−0.001 (4)
C1	0.034 (5)	0.046 (6)	0.023 (5)	0.009 (4)	0.004 (4)	0.008 (4)
C6	0.037 (5)	0.024 (5)	0.016 (4)	0.009 (4)	−0.002 (4)	0.001 (4)
C12	0.028 (5)	0.014 (4)	0.022 (5)	0.000 (3)	0.003 (4)	0.003 (3)
C7	0.037 (5)	0.034 (5)	0.021 (5)	−0.013 (4)	0.008 (4)	−0.008 (4)
O7	0.048 (4)	0.026 (3)	0.038 (4)	−0.004 (3)	−0.001 (3)	0.009 (3)
O8	0.069 (5)	0.044 (4)	0.026 (4)	−0.011 (3)	−0.011 (3)	−0.003 (3)
C8	0.039 (5)	0.053 (5)	0.025 (4)	−0.005 (4)	0.013 (4)	0.023 (4)
C2	0.051 (6)	0.040 (6)	0.025 (5)	0.009 (5)	−0.003 (4)	−0.007 (5)
C3	0.064 (7)	0.043 (6)	0.029 (6)	0.018 (5)	0.000 (5)	0.004 (5)
C20	0.034 (5)	0.037 (5)	0.015 (4)	0.002 (4)	0.001 (4)	−0.006 (4)
C21	0.096 (9)	0.028 (6)	0.052 (7)	−0.001 (6)	0.001 (6)	−0.007 (5)
C10	0.114 (11)	0.071 (9)	0.040 (7)	−0.029 (7)	−0.024 (7)	−0.014 (6)
C9	0.174 (17)	0.064 (9)	0.097 (11)	−0.052 (10)	0.006 (10)	0.011 (8)

C13—C14	1.375 (11)	C16—C17	1.369 (10)
C13—C12	1.400 (10)	C19—N2	1.489 (10)
C13—Br8	1.883 (8)	C19—C20	1.509 (10)
Br5—C16	1.915 (8)	C19—H19A	0.9700
Br7—C14	1.882 (7)	C19—H19B	0.9700
Br1—C1	1.914 (9)	C17—C12	1.394 (11)
Br6—C15	1.877 (8)	C17—C18	1.533 (11)
Br3—C3	1.891 (10)	N2—H2A	0.8900
Br4—C4	1.880 (9)	N2—H2B	0.8900
Br2—C2	1.869 (9)	N2—H2C	0.8900
O5—C18	1.272 (9)	O4—C8	1.284 (10)
O6—C18	1.240 (9)	O4—C9	1.434 (13)
O2—C7	1.253 (10)	O3—C8	1.158 (10)
O9—C21	1.404 (10)	C1—C6	1.381 (11)
O9—H9	0.8200	C1—C2	1.387 (12)
C15—C14	1.382 (11)	C6—C7	1.532 (11)
C15—C16	1.389 (10)	O8—C10	1.436 (10)
N1—C20	1.478 (10)	C2—C3	1.369 (13)
N1—H1A	0.8900	C20—H20A	0.9700
N1—H1B	0.8900	C20—H20B	0.9700
N1—H1C	0.8900	C21—H21A	0.9600
C4—C3	1.388 (13)	C21—H21B	0.9600
C4—C5	1.424 (12)	C21—H21C	0.9600
C5—C6	1.405 (11)	C10—H10A	0.9600
C5—C8	1.512 (13)	C10—H10B	0.9600
C11—O7	1.197 (9)	C10—H10C	0.9600
C11—O8	1.321 (10)	C9—H9A	0.9600
C11—C12	1.506 (11)	C9—H9B	0.9600
O1—C7	1.215 (10)	C9—H9C	0.9600
?···?	?
C14—C13—C12	119.9 (7)	C6—C1—C2	122.7 (8)
C14—C13—Br8	121.6 (6)	C6—C1—Br1	117.1 (6)
C12—C13—Br8	118.5 (6)	C2—C1—Br1	120.1 (7)
C21—O9—H9	109.5	C1—C6—C5	118.8 (8)
C14—C15—C16	118.9 (7)	C1—C6—C7	121.4 (8)
C14—C15—Br6	120.1 (6)	C5—C6—C7	119.7 (7)
C16—C15—Br6	120.9 (6)	C17—C12—C13	119.9 (7)
C20—N1—H1A	109.5	C17—C12—C11	118.6 (7)
C20—N1—H1B	109.5	C13—C12—C11	121.3 (7)
H1A—N1—H1B	109.5	O1—C7—O2	128.7 (8)
C20—N1—H1C	109.5	O1—C7—C6	116.8 (8)
H1A—N1—H1C	109.5	O2—C7—C6	114.4 (8)
H1B—N1—H1C	109.5	C11—O8—C10	116.3 (8)
C13—C14—C15	120.5 (7)	O3—C8—O4	127.9 (10)
C13—C14—Br7	119.0 (6)	O3—C8—C5	122.3 (8)
C15—C14—Br7	120.5 (6)	O4—C8—C5	109.6 (8)
C3—C4—C5	120.4 (9)	C3—C2—C1	119.0 (9)
C3—C4—Br4	121.5 (7)	C3—C2—Br2	120.5 (7)
C5—C4—Br4	118.0 (8)	C1—C2—Br2	120.5 (8)
C6—C5—C4	118.5 (8)	C2—C3—C4	120.6 (9)
C6—C5—C8	118.4 (7)	C2—C3—Br3	120.6 (8)
C4—C5—C8	123.1 (8)	C4—C3—Br3	118.8 (8)
O7—C11—O8	125.6 (8)	N1—C20—C19	109.7 (6)
O7—C11—C12	123.4 (8)	N1—C20—H20A	109.7
O8—C11—C12	111.0 (7)	C19—C20—H20A	109.7
C17—C16—C15	121.9 (7)	N1—C20—H20B	109.7
C17—C16—Br5	119.1 (6)	C19—C20—H20B	109.7
C15—C16—Br5	118.9 (6)	H20A—C20—H20B	108.2
N2—C19—C20	109.9 (6)	O9—C21—H21A	109.5
N2—C19—H19A	109.7	O9—C21—H21B	109.5
C20—C19—H19A	109.7	H21A—C21—H21B	109.5
N2—C19—H19B	109.7	O9—C21—H21C	109.5
C20—C19—H19B	109.7	H21A—C21—H21C	109.5
H19A—C19—H19B	108.2	H21B—C21—H21C	109.5
C16—C17—C12	118.8 (7)	O8—C10—H10A	109.5
C16—C17—C18	123.3 (7)	O8—C10—H10B	109.5
C12—C17—C18	117.7 (7)	H10A—C10—H10B	109.5
C19—N2—H2A	109.5	O8—C10—H10C	109.5
C19—N2—H2B	109.5	H10A—C10—H10C	109.5
H2A—N2—H2B	109.5	H10B—C10—H10C	109.5
C19—N2—H2C	109.5	O4—C9—H9A	109.5
H2A—N2—H2C	109.5	O4—C9—H9B	109.5
H2B—N2—H2C	109.5	H9A—C9—H9B	109.5
C8—O4—C9	114.2 (9)	O4—C9—H9C	109.5
O6—C18—O5	125.7 (7)	H9A—C9—H9C	109.5
O6—C18—C17	117.0 (7)	H9B—C9—H9C	109.5
O5—C18—C17	117.2 (7)
C12—C13—C14—C15	0.6 (12)	C18—C17—C12—C11	5.4 (11)
Br8—C13—C14—C15	−178.6 (6)	C14—C13—C12—C17	2.8 (12)
C12—C13—C14—Br7	−179.8 (6)	Br8—C13—C12—C17	−178.0 (6)
Br8—C13—C14—Br7	1.0 (9)	C14—C13—C12—C11	177.7 (7)
C16—C15—C14—C13	−1.9 (12)	Br8—C13—C12—C11	−3.1 (10)
Br6—C15—C14—C13	175.4 (6)	O7—C11—C12—C17	62.5 (11)
C16—C15—C14—Br7	178.6 (6)	O8—C11—C12—C17	−117.7 (8)
Br6—C15—C14—Br7	−4.1 (10)	O7—C11—C12—C13	−112.4 (10)
C3—C4—C5—C6	−0.2 (12)	O8—C11—C12—C13	67.4 (10)
Br4—C4—C5—C6	175.6 (6)	C1—C6—C7—O1	101.9 (10)
C3—C4—C5—C8	177.3 (8)	C5—C6—C7—O1	−81.3 (10)
Br4—C4—C5—C8	−6.9 (11)	C1—C6—C7—O2	−79.9 (10)
C14—C15—C16—C17	−0.3 (13)	C5—C6—C7—O2	96.9 (9)
Br6—C15—C16—C17	−177.6 (6)	O7—C11—O8—C10	9.4 (13)
C14—C15—C16—Br5	−176.8 (6)	C12—C11—O8—C10	−170.4 (8)
Br6—C15—C16—Br5	5.9 (9)	C9—O4—C8—O3	−8.1 (16)
C15—C16—C17—C12	3.7 (12)	C9—O4—C8—C5	175.6 (10)
Br5—C16—C17—C12	−179.8 (6)	C6—C5—C8—O3	−54.1 (13)
C15—C16—C17—C18	178.1 (8)	C4—C5—C8—O3	128.5 (10)
Br5—C16—C17—C18	−5.4 (11)	C6—C5—C8—O4	122.5 (8)
C16—C17—C18—O6	−119.1 (9)	C4—C5—C8—O4	−55.0 (11)
C12—C17—C18—O6	55.3 (10)	C6—C1—C2—C3	−1.0 (13)
C16—C17—C18—O5	63.1 (11)	Br1—C1—C2—C3	−178.1 (7)
C12—C17—C18—O5	−122.5 (8)	C6—C1—C2—Br2	179.1 (6)
C2—C1—C6—C5	0.1 (12)	Br1—C1—C2—Br2	2.0 (10)
Br1—C1—C6—C5	177.3 (6)	C1—C2—C3—C4	1.3 (14)
C2—C1—C6—C7	176.9 (8)	Br2—C2—C3—C4	−178.8 (6)
Br1—C1—C6—C7	−5.9 (10)	C1—C2—C3—Br3	−177.4 (6)
C4—C5—C6—C1	0.5 (12)	Br2—C2—C3—Br3	2.4 (11)
C8—C5—C6—C1	−177.1 (7)	C5—C4—C3—C2	−0.7 (13)
C4—C5—C6—C7	−176.4 (7)	Br4—C4—C3—C2	−176.4 (7)
C8—C5—C6—C7	6.0 (12)	C5—C4—C3—Br3	178.0 (6)
C16—C17—C12—C13	−4.9 (12)	Br4—C4—C3—Br3	2.4 (10)
C18—C17—C12—C13	−179.6 (7)	N2—C19—C20—N1	166.0 (6)
C16—C17—C12—C11	−179.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	1.87	2.748 (8)	167
N1—H1B···O5ii	0.89	2.04	2.857 (8)	153
N1—H1C···O6	0.89	1.86	2.734 (8)	166
N2—H2A···O9iii	0.89	1.97	2.801 (9)	154
N2—H2B···O2iii	0.89	1.93	2.795 (9)	163
N2—H2B···O3iii	0.89	2.57	3.000 (9)	110
N2—H2C···O5iv	0.89	1.90	2.747 (9)	159
O9—H9···O1v	0.82	1.89	2.695 (8)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	1.87	2.748 (8)	167
N1—H1B⋯O5ii	0.89	2.04	2.857 (8)	153
N1—H1C⋯O6	0.89	1.86	2.734 (8)	166
N2—H2A⋯O9iii	0.89	1.97	2.801 (9)	154
N2—H2B⋯O2iii	0.89	1.93	2.795 (9)	163
N2—H2B⋯O3iii	0.89	2.57	3.000 (9)	110
N2—H2C⋯O5iv	0.89	1.90	2.747 (9)	159
O9—H9⋯O1v	0.82	1.89	2.695 (8)	168

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