4-Amino-2-methyl-quinolinium hydrogensulfate dihydrate.

In the title compound, C(10)H(11)N(2) (+)·HSO(4) (-)·2H(2)O, the asymmetric unit contains two protonated 4-amino-quinoline cations and two hydrogen sulfate anions with four water mol-ecules. The crystal structure involves extensive N-H⋯O and O-H⋯O hydrogen bonding.

Related literature

For related literature, see: Amini et al. (2007a ▶,b ▶); Repicky et al. (2005 ▶).

Experimental

Crystal data

C10H11N2 +·HSO4 −·2H2O

M = 292.32

Triclinic,

a = 10.1585 (9) Å

b = 11.2131 (9) Å

c = 13.3545 (11) Å

α = 68.283 (6)°

β = 76.355 (7)°

γ = 67.949 (6)°

V = 1301.51 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 120 (2) K

0.5 × 0.15 × 0.12 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.950, T max = 0.970

16357 measured reflections

7008 independent reflections

5729 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.182

S = 1.06

7008 reflections

409 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.99 e Å−3

Data collection: X-RED32 (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063982/om2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063982/om2193Isup2.hkl

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

C10H11N2+·HSO4–·2H2O	Z = 4
Mr = 292.32	F000 = 616
Triclinic, P1	Dx = 1.492 Mg m−3
a = 10.1585 (9) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.2131 (9) Å	Cell parameters from 2500 reflections
c = 13.3545 (11) Å	θ = 1.7–29.2º
α = 68.283 (6)º	µ = 0.27 mm−1
β = 76.355 (7)º	T = 120 (2) K
γ = 67.949 (6)º	Needle, colorless
V = 1301.51 (19) Å3	0.5 × 0.15 × 0.12 mm

Stoe IPDSII diffractometer	Rint = 0.087
ω scans	θmax = 29.2º
Absorption correction: numerical(X-SHAPE; Stoe & Cie, 2005)	θmin = 1.7º
Tmin = 0.950, Tmax = 0.970	h = −13→13
16357 measured reflections	k = −15→15
7008 independent reflections	l = −18→16
5729 reflections with I > 2σ(I)

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0853P)2 + 1.1102P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060	(Δ/σ)max = 0.019
wR(F2) = 0.182	Δρmax = 0.39 e Å−3
S = 1.06	Δρmin = −0.99 e Å−3
7008 reflections	Extinction correction: none
409 parameters

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.

	x	y	z	Uiso*/Ueq
C1	−0.2667 (2)	0.3412 (2)	0.37942 (17)	0.0230 (4)
H1A	−0.1789	0.3565	0.3583	0.028*
C2	−0.2725 (2)	0.2116 (2)	0.42028 (19)	0.0251 (4)
H2A	−0.1882	0.1389	0.4268	0.03*
C3	−0.4052 (2)	0.1875 (2)	0.45255 (19)	0.0251 (4)
H3A	−0.408	0.0991	0.48	0.03*
C4	−0.5305 (2)	0.2943 (2)	0.44357 (17)	0.0228 (4)
H4A	−0.6174	0.2772	0.4648	0.027*
C5	−0.5292 (2)	0.4296 (2)	0.40258 (16)	0.0206 (4)
C6	−0.6557 (2)	0.5461 (2)	0.39237 (17)	0.0208 (4)
C7	−0.6404 (2)	0.6757 (2)	0.34890 (17)	0.0228 (4)
H7	−0.7215	0.7519	0.3411	0.027*
C8	−0.5072 (2)	0.6914 (2)	0.31778 (17)	0.0217 (4)
C9	−0.4852 (3)	0.8274 (2)	0.27189 (19)	0.0274 (5)
H9C	−0.4342	0.8368	0.2005	0.033*
H9B	−0.4311	0.8351	0.3179	0.033*
H9A	−0.5764	0.8973	0.2679	0.033*
C10	−0.3942 (2)	0.4510 (2)	0.36953 (17)	0.0205 (4)
C11	−0.7437 (2)	0.6655 (2)	0.12158 (18)	0.0240 (4)
H11A	−0.8339	0.6553	0.1415	0.029*
C12	−0.7303 (2)	0.7924 (2)	0.08060 (19)	0.0268 (4)
H12A	−0.8116	0.8683	0.0736	0.032*
C13	−0.5935 (2)	0.8088 (2)	0.04894 (19)	0.0257 (4)
H13	−0.5854	0.8953	0.0208	0.031*
C14	−0.4726 (2)	0.6974 (2)	0.05956 (17)	0.0230 (4)
H14	−0.3832	0.7093	0.0386	0.028*
C15	−0.4823 (2)	0.5647 (2)	0.10199 (16)	0.0203 (4)
C16	−0.3599 (2)	0.4439 (2)	0.11442 (17)	0.0202 (4)
C17	−0.3833 (2)	0.3176 (2)	0.15913 (17)	0.0217 (4)
H17	−0.3055	0.2385	0.1688	0.026*
C18	−0.5200 (2)	0.3094 (2)	0.18876 (17)	0.0216 (4)
C19	−0.5493 (2)	0.1767 (2)	0.23516 (18)	0.0253 (4)
H19A	−0.4617	0.1044	0.253	0.03*
H19B	−0.5889	0.1641	0.1827	0.03*
H19C	−0.6159	0.1767	0.2995	0.03*
C20	−0.6205 (2)	0.5506 (2)	0.13349 (17)	0.0207 (4)
N1	−0.7861 (2)	0.5326 (2)	0.42328 (17)	0.0264 (4)
H1B	−0.799 (3)	0.452 (3)	0.450 (2)	0.035 (8)*
H1C	−0.863 (3)	0.604 (3)	0.421 (2)	0.034 (8)*
N2	−0.38895 (19)	0.58169 (19)	0.32826 (15)	0.0215 (4)
H2B	−0.297 (3)	0.591 (3)	0.304 (2)	0.033 (8)*
N3	−0.2264 (2)	0.4497 (2)	0.08604 (16)	0.0241 (4)
H3B	−0.206 (3)	0.528 (3)	0.056 (3)	0.041 (9)*
H3C	−0.156 (3)	0.375 (3)	0.090 (2)	0.030 (7)*
N4	−0.63363 (19)	0.42260 (19)	0.17560 (15)	0.0217 (4)
H4B	−0.724 (3)	0.421 (3)	0.197 (2)	0.024 (7)*
O1	0.21598 (18)	0.09186 (18)	0.12957 (15)	0.0304 (4)
H1D	0.174 (4)	0.085 (4)	0.196 (3)	0.049 (10)*
O2	0.19440 (18)	0.16254 (17)	−0.05753 (13)	0.0285 (4)
O3	0.11031 (19)	0.33038 (17)	0.03498 (15)	0.0316 (4)
O4	−0.02002 (17)	0.17733 (17)	0.07138 (14)	0.0279 (4)
O5	−0.21953 (18)	−0.06596 (18)	0.35374 (15)	0.0299 (4)
H5	−0.169 (4)	−0.059 (4)	0.284 (3)	0.054 (10)*
O6	−0.20017 (18)	−0.15065 (18)	0.54201 (14)	0.0307 (4)
O7	−0.10350 (19)	−0.30542 (17)	0.43617 (14)	0.0306 (4)
O8	0.01481 (18)	−0.14707 (19)	0.41604 (15)	0.0328 (4)
O9	0.1039 (3)	0.0757 (2)	0.31884 (16)	0.0445 (5)
H9D	0.080 (4)	0.007 (4)	0.356 (3)	0.056 (11)*
H9E	0.133 (4)	0.098 (4)	0.358 (3)	0.047 (10)*
O10	−0.0982 (2)	−0.0478 (2)	0.16311 (16)	0.0396 (5)
H10A	−0.073 (4)	0.026 (4)	0.129 (3)	0.050 (10)*
H10B	−0.127 (4)	−0.073 (3)	0.124 (3)	0.042 (9)*
O11	−0.12512 (18)	−0.36765 (18)	0.25826 (15)	0.0276 (4)
H11C	−0.112 (3)	−0.346 (3)	0.309 (3)	0.038 (8)*
H11B	−0.137 (4)	−0.303 (4)	0.203 (3)	0.070 (13)*
O12	−0.90519 (19)	0.4039 (2)	0.21908 (16)	0.0316 (4)
H12B	−0.916 (4)	0.386 (4)	0.165 (3)	0.058 (11)*
H12C	−0.979 (4)	0.478 (4)	0.231 (3)	0.063 (11)*
S1	0.12067 (5)	0.19469 (5)	0.04176 (4)	0.02081 (14)
S2	−0.12161 (5)	−0.17207 (5)	0.44180 (4)	0.02107 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0200 (10)	0.0298 (11)	0.0256 (10)	−0.0120 (8)	−0.0022 (8)	−0.0116 (8)
C2	0.0199 (10)	0.0276 (11)	0.0317 (11)	−0.0074 (8)	−0.0033 (8)	−0.0137 (9)
C3	0.0260 (11)	0.0250 (10)	0.0304 (11)	−0.0135 (9)	−0.0012 (8)	−0.0111 (8)
C4	0.0205 (10)	0.0282 (11)	0.0258 (10)	−0.0132 (8)	−0.0009 (8)	−0.0108 (8)
C5	0.0196 (9)	0.0262 (10)	0.0220 (9)	−0.0122 (8)	−0.0019 (7)	−0.0095 (8)
C6	0.0168 (9)	0.0281 (10)	0.0224 (9)	−0.0096 (8)	−0.0002 (7)	−0.0118 (8)
C7	0.0223 (10)	0.0237 (10)	0.0258 (10)	−0.0077 (8)	−0.0040 (8)	−0.0102 (8)
C8	0.0222 (10)	0.0240 (10)	0.0228 (9)	−0.0099 (8)	−0.0033 (7)	−0.0086 (8)
C9	0.0317 (12)	0.0254 (11)	0.0297 (11)	−0.0148 (9)	−0.0041 (9)	−0.0076 (8)
C10	0.0197 (9)	0.0247 (10)	0.0230 (9)	−0.0109 (8)	−0.0022 (7)	−0.0102 (8)
C11	0.0184 (9)	0.0310 (11)	0.0278 (10)	−0.0109 (8)	−0.0033 (8)	−0.0113 (8)
C12	0.0213 (10)	0.0281 (11)	0.0329 (11)	−0.0059 (8)	−0.0057 (8)	−0.0121 (9)
C13	0.0266 (11)	0.0245 (10)	0.0307 (11)	−0.0120 (9)	−0.0034 (9)	−0.0098 (8)
C14	0.0213 (10)	0.0275 (10)	0.0253 (10)	−0.0126 (8)	−0.0030 (8)	−0.0086 (8)
C15	0.0192 (9)	0.0264 (10)	0.0212 (9)	−0.0112 (8)	−0.0019 (7)	−0.0101 (8)
C16	0.0178 (9)	0.0268 (10)	0.0225 (9)	−0.0113 (8)	−0.0015 (7)	−0.0109 (8)
C17	0.0176 (9)	0.0252 (10)	0.0278 (10)	−0.0091 (8)	−0.0035 (8)	−0.0115 (8)
C18	0.0201 (9)	0.0260 (10)	0.0242 (10)	−0.0121 (8)	−0.0025 (7)	−0.0091 (8)
C19	0.0258 (10)	0.0272 (11)	0.0288 (11)	−0.0154 (9)	−0.0009 (8)	−0.0097 (8)
C20	0.0192 (9)	0.0251 (10)	0.0228 (9)	−0.0102 (8)	−0.0035 (7)	−0.0092 (8)
N1	0.0177 (9)	0.0285 (10)	0.0355 (10)	−0.0099 (8)	−0.0012 (7)	−0.0112 (8)
N2	0.0199 (8)	0.0259 (9)	0.0248 (8)	−0.0121 (7)	−0.0015 (7)	−0.0106 (7)
N3	0.0160 (9)	0.0269 (10)	0.0325 (10)	−0.0104 (8)	−0.0011 (7)	−0.0101 (8)
N4	0.0171 (8)	0.0292 (9)	0.0255 (9)	−0.0130 (7)	−0.0011 (6)	−0.0109 (7)
O1	0.0226 (8)	0.0384 (10)	0.0315 (9)	−0.0084 (7)	−0.0048 (7)	−0.0127 (7)
O2	0.0302 (8)	0.0337 (9)	0.0284 (8)	−0.0149 (7)	0.0030 (6)	−0.0162 (7)
O3	0.0305 (9)	0.0282 (8)	0.0435 (10)	−0.0172 (7)	0.0046 (7)	−0.0167 (7)
O4	0.0183 (7)	0.0330 (9)	0.0387 (9)	−0.0157 (7)	−0.0021 (6)	−0.0111 (7)
O5	0.0238 (8)	0.0329 (9)	0.0346 (9)	−0.0071 (7)	−0.0045 (7)	−0.0135 (7)
O6	0.0300 (9)	0.0380 (9)	0.0305 (8)	−0.0175 (7)	0.0027 (7)	−0.0148 (7)
O7	0.0325 (9)	0.0268 (8)	0.0367 (9)	−0.0127 (7)	−0.0027 (7)	−0.0121 (7)
O8	0.0206 (8)	0.0443 (10)	0.0398 (10)	−0.0194 (7)	−0.0011 (7)	−0.0124 (8)
O9	0.0656 (14)	0.0587 (13)	0.0308 (10)	−0.0463 (12)	0.0001 (9)	−0.0143 (9)
O10	0.0614 (13)	0.0439 (11)	0.0288 (9)	−0.0365 (10)	−0.0023 (8)	−0.0099 (8)
O11	0.0253 (8)	0.0320 (9)	0.0328 (9)	−0.0150 (7)	−0.0018 (7)	−0.0130 (7)
O12	0.0208 (8)	0.0380 (10)	0.0445 (10)	−0.0133 (7)	−0.0023 (7)	−0.0191 (8)
S1	0.0171 (3)	0.0242 (3)	0.0272 (3)	−0.0123 (2)	−0.00033 (19)	−0.0103 (2)
S2	0.0170 (3)	0.0253 (3)	0.0263 (3)	−0.0114 (2)	−0.00057 (19)	−0.0105 (2)

C1—C2	1.369 (3)	C16—C17	1.407 (3)
C1—C10	1.405 (3)	C17—C18	1.380 (3)
C1—H1A	0.93	C17—H17	0.93
C2—C3	1.411 (3)	C18—N4	1.344 (3)
C2—H2A	0.93	C18—C19	1.499 (3)
C3—C4	1.374 (3)	C19—H19A	0.96
C3—H3A	0.93	C19—H19B	0.96
C4—C5	1.414 (3)	C19—H19C	0.96
C4—H4A	0.93	C20—N4	1.380 (3)
C5—C10	1.420 (3)	N1—H1B	0.89 (3)
C5—C6	1.437 (3)	N1—H1C	0.89 (3)
C6—N1	1.339 (3)	N2—H2B	0.95 (3)
C6—C7	1.406 (3)	N3—H3B	0.90 (3)
C7—C8	1.376 (3)	N3—H3C	0.86 (3)
C7—H7	0.93	N4—H4B	0.90 (3)
C8—N2	1.348 (3)	O1—S1	1.5293 (18)
C8—C9	1.500 (3)	O1—H1D	0.87 (4)
C9—H9C	0.96	O2—S1	1.4601 (17)
C9—H9B	0.96	O3—S1	1.4548 (16)
C9—H9A	0.96	O4—S1	1.4568 (15)
C10—N2	1.379 (3)	O5—S2	1.5543 (18)
C11—C12	1.370 (3)	O5—H5	0.94 (4)
C11—C20	1.408 (3)	O6—S2	1.4406 (17)
C11—H11A	0.93	O7—S2	1.4646 (17)
C12—C13	1.414 (3)	O8—S2	1.4536 (15)
C12—H12A	0.93	O9—H9D	0.84 (4)
C13—C14	1.374 (3)	O9—H9E	0.81 (4)
C13—H13	0.93	O10—H10A	0.88 (4)
C14—C15	1.415 (3)	O10—H10B	0.82 (3)
C14—H14	0.93	O11—H11C	0.85 (3)
C15—C20	1.419 (3)	O11—H11B	0.82 (4)
C15—C16	1.440 (3)	O12—H12B	0.86 (4)
C16—N3	1.339 (2)	O12—H12C	0.92 (4)
C2—C1—C10	119.60 (19)	N3—C16—C17	120.0 (2)
C2—C1—H1A	120.2	N3—C16—C15	121.66 (19)
C10—C1—H1A	120.2	C17—C16—C15	118.32 (18)
C1—C2—C3	120.6 (2)	C18—C17—C16	121.0 (2)
C1—C2—H2A	119.7	C18—C17—H17	119.5
C3—C2—H2A	119.7	C16—C17—H17	119.5
C4—C3—C2	120.19 (19)	N4—C18—C17	120.30 (19)
C4—C3—H3A	119.9	N4—C18—C19	117.20 (18)
C2—C3—H3A	119.9	C17—C18—C19	122.5 (2)
C3—C4—C5	121.01 (19)	C18—C19—H19A	109.5
C3—C4—H4A	119.5	C18—C19—H19B	109.5
C5—C4—H4A	119.5	H19A—C19—H19B	109.5
C4—C5—C10	117.63 (19)	C18—C19—H19C	109.5
C4—C5—C6	124.08 (18)	H19A—C19—H19C	109.5
C10—C5—C6	118.30 (18)	H19B—C19—H19C	109.5
N1—C6—C7	120.1 (2)	N4—C20—C11	119.97 (18)
N1—C6—C5	121.16 (19)	N4—C20—C15	119.33 (19)
C7—C6—C5	118.71 (18)	C11—C20—C15	120.70 (19)
C8—C7—C6	120.9 (2)	C6—N1—H1B	122 (2)
C8—C7—H7	119.6	C6—N1—H1C	120.9 (19)
C6—C7—H7	119.6	H1B—N1—H1C	117 (3)
N2—C8—C7	120.14 (19)	C8—N2—C10	122.78 (17)
N2—C8—C9	116.95 (18)	C8—N2—H2B	121.3 (18)
C7—C8—C9	122.9 (2)	C10—N2—H2B	115.9 (18)
C8—C9—H9C	109.5	C16—N3—H3B	123 (2)
C8—C9—H9B	109.5	C16—N3—H3C	118.9 (19)
H9C—C9—H9B	109.5	H3B—N3—H3C	118 (3)
C8—C9—H9A	109.5	C18—N4—C20	122.61 (17)
H9C—C9—H9A	109.5	C18—N4—H4B	122.8 (17)
H9B—C9—H9A	109.5	C20—N4—H4B	114.6 (17)
N2—C10—C1	119.84 (18)	S1—O1—H1D	114 (2)
N2—C10—C5	119.20 (19)	S2—O5—H5	111 (2)
C1—C10—C5	120.96 (19)	H9D—O9—H9E	109 (4)
C12—C11—C20	119.83 (19)	H10A—O10—H10B	114 (3)
C12—C11—H11A	120.1	H11C—O11—H11B	111 (3)
C20—C11—H11A	120.1	H12B—O12—H12C	111 (3)
C11—C12—C13	120.4 (2)	O3—S1—O4	110.45 (10)
C11—C12—H12A	119.8	O3—S1—O2	111.62 (10)
C13—C12—H12A	119.8	O4—S1—O2	112.86 (10)
C14—C13—C12	120.2 (2)	O3—S1—O1	108.74 (10)
C14—C13—H13	119.9	O4—S1—O1	108.47 (10)
C12—C13—H13	119.9	O2—S1—O1	104.41 (10)
C13—C14—C15	120.93 (19)	O6—S2—O8	113.87 (10)
C13—C14—H14	119.5	O6—S2—O7	112.78 (10)
C15—C14—H14	119.5	O8—S2—O7	110.74 (11)
C14—C15—C20	117.89 (19)	O6—S2—O5	104.17 (10)
C14—C15—C16	123.65 (18)	O8—S2—O5	108.13 (10)
C20—C15—C16	118.47 (18)	O7—S2—O5	106.56 (10)
C10—C1—C2—C3	0.0 (3)	C13—C14—C15—C16	179.5 (2)
C1—C2—C3—C4	−0.2 (3)	C14—C15—C16—N3	0.0 (3)
C2—C3—C4—C5	−0.3 (3)	C20—C15—C16—N3	179.79 (19)
C3—C4—C5—C10	1.0 (3)	C14—C15—C16—C17	179.10 (19)
C3—C4—C5—C6	−179.1 (2)	C20—C15—C16—C17	−1.2 (3)
C4—C5—C6—N1	0.8 (3)	N3—C16—C17—C18	−179.9 (2)
C10—C5—C6—N1	−179.22 (19)	C15—C16—C17—C18	1.0 (3)
C4—C5—C6—C7	−179.12 (19)	C16—C17—C18—N4	−0.2 (3)
C10—C5—C6—C7	0.8 (3)	C16—C17—C18—C19	179.12 (19)
N1—C6—C7—C8	179.3 (2)	C12—C11—C20—N4	179.5 (2)
C5—C6—C7—C8	−0.7 (3)	C12—C11—C20—C15	−0.9 (3)
C6—C7—C8—N2	0.3 (3)	C14—C15—C20—N4	−179.74 (18)
C6—C7—C8—C9	−179.5 (2)	C16—C15—C20—N4	0.5 (3)
C2—C1—C10—N2	−179.89 (19)	C14—C15—C20—C11	0.7 (3)
C2—C1—C10—C5	0.8 (3)	C16—C15—C20—C11	−179.10 (19)
C4—C5—C10—N2	179.44 (18)	C7—C8—N2—C10	0.1 (3)
C6—C5—C10—N2	−0.5 (3)	C9—C8—N2—C10	179.83 (18)
C4—C5—C10—C1	−1.3 (3)	C1—C10—N2—C8	−179.24 (19)
C6—C5—C10—C1	178.79 (19)	C5—C10—N2—C8	0.1 (3)
C20—C11—C12—C13	0.8 (3)	C17—C18—N4—C20	−0.5 (3)
C11—C12—C13—C14	−0.4 (3)	C19—C18—N4—C20	−179.86 (18)
C12—C13—C14—C15	0.1 (3)	C11—C20—N4—C18	179.95 (19)
C13—C14—C15—C20	−0.2 (3)	C15—C20—N4—C18	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O7i	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1—H1C···O7ii	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1—H1C···O8ii	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1—H1D···O9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2—H2B···O11iii	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3—H3B···O3iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3—H3C···O3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3—H3C···O4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4—H4B···O12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5—H5···O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9—H9D···O8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9—H9E···O6v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10—H10A···O4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10—H10B···O2vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11—H11B···O2vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11—H11C···O7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12—H12B···O3vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12—H12C···O11ii	0.92 (4)	1.90 (4)	2.823 (3)	177 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O7i	0.89 (3)	2.16 (3)	2.981 (3)	154 (3)
N1—H1C⋯O7ii	0.88 (3)	2.26 (3)	3.049 (3)	149 (3)
N1—H1C⋯O8ii	0.88 (3)	2.58 (3)	3.374 (3)	151 (3)
O1—H1D⋯O9	0.88 (4)	1.61 (4)	2.485 (3)	177 (5)
N2—H2B⋯O11iii	0.95 (3)	1.88 (3)	2.819 (3)	172 (3)
N3—H3B⋯O3iv	0.90 (3)	2.03 (3)	2.902 (3)	163 (3)
N3—H3C⋯O3	0.87 (3)	2.54 (3)	3.177 (3)	132 (3)
N3—H3C⋯O4	0.87 (3)	2.20 (3)	3.034 (3)	162 (3)
N4—H4B⋯O12	0.90 (3)	1.87 (3)	2.753 (3)	169 (3)
O5—H5⋯O10	0.94 (4)	1.58 (4)	2.523 (3)	174 (5)
O9—H9D⋯O8	0.84 (4)	1.91 (4)	2.736 (3)	169 (4)
O9—H9E⋯O6v	0.81 (4)	1.98 (4)	2.783 (3)	178 (5)
O10—H10A⋯O4	0.89 (4)	1.81 (4)	2.695 (3)	175 (3)
O10—H10B⋯O2vi	0.83 (4)	1.93 (4)	2.745 (3)	169 (4)
O11—H11B⋯O2vi	0.82 (4)	2.04 (4)	2.843 (3)	167 (5)
O11—H11C⋯O7	0.85 (4)	1.94 (4)	2.787 (3)	172 (3)
O12—H12B⋯O3vii	0.86 (4)	1.98 (4)	2.823 (3)	166 (4)
O12—H12C⋯O11ii	0.92 (4)	1.90 (4)	2.823 (3)	177 (4)

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