Bis(tetra-ethyl-ammonium) bis-(hydrogen l-tartrate) l-tartaric acid monohydrate.

In the title compound, 2C(8)H(20)N(+)·2C(4)H(5)O(6) (-)·C(4)H(6)O(6)·H(2)O, the presence of the two tetra-ethyl-ammonium cations is balanced by two hydrogen l-tartrate anions. Also present in the asymmetric unit are a mol-ecule of l-tartaric acid and a water mol-ecule. The various components are linked by O-H⋯O hydrogen bonds. In the crystal, two-dimensional networks are formed via O-H⋯O hydrogen bonds and C-H⋯O inter-actions involving the water mol-ecule, the hydrogen l-tartrate anions and the l-tartaric acid mol-ecules. These layers, which stack along [001], are separated by tetra-ethyl-ammonium cations. The latter are also involved in C-H⋯O inter-actions with the anions and the l-tartaric acid and water mol-ecules participating in the two-dimensional network.

Related literature

For potential industrial applications of non-linear optical (NLO) materials, see: Dega-Szafran et al. (2008 ▶); Bosshard et al. (1995 ▶). For an example of a structure showing bulk quadratic NLO effects, see: Coe et al. (2005 ▶). For the crystal structure of tetra­ethyl­ammonium hydrogen l-tartrate dihydrate, see: Rahman et al. (2008 ▶).

Experimental

Crystal data

2C8H20N+·2C4H5O6 −·C4H6O6·H2O

M = 726.76

Monoclinic,

a = 7.5725 (4) Å

b = 27.7907 (13) Å

c = 8.7620 (6) Å

β = 99.884 (5)°

V = 1816.55 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.45 × 0.32 × 0.25 mm

Data collection

Stoe IPDS 2 diffractometer

20250 measured reflections

3502 independent reflections

3116 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.064

S = 1.03

3502 reflections

469 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015479/nr2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015479/nr2003Isup2.hkl

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

2C8H20N+·2C4H5O6−·C4H6O6·H2O	F(000) = 784
Mr = 726.76	Dx = 1.329 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 16128 reflections
a = 7.5725 (4) Å	θ = 1.5–25.7°
b = 27.7907 (13) Å	µ = 0.11 mm−1
c = 8.7620 (6) Å	T = 173 K
β = 99.884 (5)°	Rod, colourless
V = 1816.55 (18) Å3	0.45 × 0.32 × 0.25 mm
Z = 2

Stoe IPDS 2 diffractometer	3116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
graphite	θmax = 25.7°, θmin = 1.5°
φ and ω scans	h = −9→9
20250 measured reflections	k = −33→33
3502 independent reflections	l = −10→10

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0336P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3502 reflections	Δρmax = 0.17 e Å−3
469 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (10)

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. The water H-atoms were located in difference electron-density maps and refined with O—H distance restraints of 0.84 (2) Å, and Uiso(H) = 1.5 × Ueq(O). The OH and C-bound H-atoms were included in calculated positions and treated as riding atoms: O—H = 0.84 Å, C—H = 1.0, 0.99 and 0.98Å for CH, CH2, and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(C or O), where k = 1.5 for OH and CH3 H-atoms, and k = 1.2 for all other H-atoms.

	x	y	z	Uiso*/Ueq
O1	0.8300 (2)	0.28144 (6)	0.5505 (2)	0.0269 (4)
O2	0.9206 (2)	0.23806 (7)	0.3631 (2)	0.0337 (5)
O3	0.6051 (2)	0.19685 (6)	0.27276 (19)	0.0251 (4)
H3O	0.7027	0.1818	0.2838	0.038*
O4	0.6211 (2)	0.17495 (6)	0.5971 (2)	0.0255 (4)
H4O	0.5879	0.1502	0.5453	0.038*
O5	0.2590 (2)	0.16831 (6)	0.4724 (2)	0.0267 (4)
O6	0.2518 (2)	0.24709 (6)	0.4224 (2)	0.0314 (4)
H6O	0.1406	0.2424	0.4023	0.047*
C1	0.8051 (3)	0.25215 (8)	0.4390 (3)	0.0199 (5)
C2	0.6153 (3)	0.23299 (9)	0.3861 (3)	0.0194 (5)
H2	0.5407	0.2606	0.3384	0.023*
C3	0.5318 (3)	0.21533 (8)	0.5243 (3)	0.0188 (5)
H3	0.5441	0.2419	0.6022	0.023*
C4	0.3328 (3)	0.20709 (9)	0.4694 (3)	0.0199 (5)
O7	0.0108 (2)	−0.03787 (6)	0.4425 (2)	0.0231 (4)
O8	−0.1122 (2)	0.02964 (6)	0.3374 (2)	0.0342 (5)
O9	0.1768 (2)	0.05712 (6)	0.2309 (2)	0.0256 (4)
H9O	0.0916	0.0746	0.2475	0.038*
O10	0.2592 (2)	0.07004 (6)	0.5647 (2)	0.0267 (4)
H10O	0.2803	0.0963	0.5242	0.040*
O11	0.5811 (3)	0.08248 (6)	0.4720 (3)	0.0391 (5)
O12	0.5832 (2)	0.00705 (6)	0.3876 (3)	0.0342 (5)
H12O	0.6874	0.0144	0.3751	0.051*
C5	0.0186 (3)	0.00157 (8)	0.3764 (3)	0.0182 (5)
C6	0.1979 (3)	0.01833 (8)	0.3365 (3)	0.0187 (5)
H6	0.2516	−0.0092	0.2870	0.022*
C7	0.3276 (3)	0.03191 (8)	0.4858 (3)	0.0204 (5)
H7	0.3407	0.0032	0.5556	0.025*
C8	0.5108 (3)	0.04356 (9)	0.4477 (3)	0.0239 (6)
O13	0.5634 (2)	0.41652 (7)	0.4106 (2)	0.0291 (4)
O14	0.7719 (2)	0.39729 (6)	0.6164 (2)	0.0266 (4)
H14O	0.8314	0.4188	0.5809	0.040*
O15	0.5743 (2)	0.32771 (6)	0.70813 (19)	0.0222 (4)
H15O	0.6599	0.3135	0.6779	0.033*
O16	0.4137 (3)	0.41234 (7)	0.7886 (2)	0.0358 (5)
H16O	0.4190	0.4418	0.7683	0.054*
O17	0.1584 (2)	0.34469 (7)	0.80706 (19)	0.0307 (4)
O18	0.1062 (2)	0.33623 (6)	0.54942 (19)	0.0244 (4)
H18O	0.0235	0.3180	0.5672	0.037*
C9	0.6136 (3)	0.39366 (8)	0.5289 (3)	0.0203 (5)
C10	0.4884 (3)	0.35829 (8)	0.5892 (3)	0.0189 (5)
H10	0.4295	0.3379	0.5009	0.023*
C11	0.3428 (3)	0.38693 (8)	0.6524 (3)	0.0199 (5)
H11	0.2910	0.4109	0.5719	0.024*
C12	0.1928 (3)	0.35356 (8)	0.6810 (3)	0.0178 (5)
N1	0.1498 (3)	0.18045 (7)	0.9192 (2)	0.0216 (4)
C13	0.0283 (4)	0.20263 (11)	1.0211 (3)	0.0311 (6)
H13A	−0.0298	0.1763	1.0704	0.037*
H13B	0.1034	0.2210	1.1049	0.037*
C14	−0.1157 (4)	0.23552 (13)	0.9396 (4)	0.0462 (8)
H14C	−0.1862	0.2482	1.0146	0.069*
H14B	−0.1944	0.2175	0.8589	0.069*
H14A	−0.0603	0.2623	0.8923	0.069*
C15	0.2489 (4)	0.21890 (9)	0.8449 (3)	0.0262 (6)
H15A	0.3226	0.2030	0.7765	0.031*
H15B	0.1597	0.2393	0.7788	0.031*
C16	0.3694 (4)	0.25100 (10)	0.9570 (3)	0.0343 (6)
H16C	0.4319	0.2736	0.8991	0.052*
H16B	0.4574	0.2312	1.0245	0.052*
H16A	0.2969	0.2689	1.0202	0.052*
C17	0.0424 (4)	0.15163 (10)	0.7866 (3)	0.0304 (6)
H17A	−0.0401	0.1739	0.7209	0.036*
H17B	0.1265	0.1386	0.7221	0.036*
C18	−0.0661 (4)	0.11051 (11)	0.8345 (4)	0.0457 (8)
H18C	−0.1327	0.0949	0.7419	0.069*
H18B	−0.1505	0.1228	0.8982	0.069*
H18A	0.0144	0.0871	0.8944	0.069*
C19	0.2818 (4)	0.14840 (10)	1.0239 (3)	0.0301 (6)
H19A	0.3407	0.1679	1.1129	0.036*
H19B	0.2134	0.1226	1.0655	0.036*
C20	0.4256 (4)	0.12536 (12)	0.9483 (4)	0.0461 (8)
H20A	0.5018	0.1505	0.9153	0.069*
H20B	0.3695	0.1067	0.8579	0.069*
H20C	0.4987	0.1040	1.0226	0.069*
N2	0.9558 (3)	0.42249 (8)	0.1066 (2)	0.0252 (5)
C21	0.8261 (4)	0.38890 (10)	0.0071 (3)	0.0318 (6)
H21A	0.7490	0.4082	−0.0730	0.038*
H21B	0.8958	0.3664	−0.0470	0.038*
C22	0.7068 (5)	0.35979 (12)	0.0949 (4)	0.0492 (8)
H22C	0.6219	0.3409	0.0214	0.074*
H22B	0.6407	0.3816	0.1526	0.074*
H22A	0.7809	0.3380	0.1673	0.074*
C23	1.0666 (4)	0.44630 (11)	−0.0008 (3)	0.0335 (6)
H23A	1.1215	0.4208	−0.0562	0.040*
H23B	0.9852	0.4651	−0.0793	0.040*
C24	1.2140 (5)	0.47937 (12)	0.0767 (5)	0.0510 (9)
H24C	1.2734	0.4943	−0.0022	0.076*
H24B	1.3017	0.4607	0.1484	0.076*
H24A	1.1622	0.5044	0.1342	0.076*
C25	0.8563 (4)	0.45954 (9)	0.1868 (3)	0.0282 (6)
H25A	0.7907	0.4426	0.2591	0.034*
H25B	0.9455	0.4808	0.2494	0.034*
C26	0.7250 (4)	0.49045 (10)	0.0805 (4)	0.0374 (7)
H26C	0.6702	0.5138	0.1421	0.056*
H26B	0.6315	0.4700	0.0222	0.056*
H26A	0.7881	0.5076	0.0083	0.056*
C27	1.0750 (4)	0.39489 (11)	0.2343 (3)	0.0377 (7)
H27A	1.1613	0.4176	0.2936	0.045*
H27B	0.9995	0.3818	0.3062	0.045*
C28	1.1785 (5)	0.35398 (12)	0.1782 (3)	0.0440 (8)
H28C	1.2500	0.3378	0.2673	0.066*
H28B	1.2580	0.3666	0.1106	0.066*
H28A	1.0945	0.3309	0.1204	0.066*
O1W	0.9034 (3)	0.13191 (8)	0.3037 (3)	0.0361 (5)
H1WA	0.873 (5)	0.1078 (16)	0.348 (5)	0.060 (12)*
H1WB	0.985 (6)	0.1475 (16)	0.370 (5)	0.069 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0211 (9)	0.0305 (9)	0.0308 (10)	−0.0086 (8)	0.0089 (8)	−0.0131 (8)
O2	0.0154 (9)	0.0414 (11)	0.0452 (12)	−0.0024 (8)	0.0077 (8)	−0.0189 (9)
O3	0.0180 (9)	0.0331 (10)	0.0232 (9)	−0.0021 (7)	0.0009 (7)	−0.0088 (8)
O4	0.0278 (10)	0.0189 (8)	0.0260 (9)	−0.0017 (8)	−0.0057 (8)	0.0017 (7)
O5	0.0242 (10)	0.0206 (9)	0.0354 (10)	−0.0068 (8)	0.0060 (8)	−0.0020 (8)
O6	0.0118 (9)	0.0243 (9)	0.0581 (13)	−0.0007 (8)	0.0065 (9)	0.0040 (9)
C1	0.0165 (12)	0.0195 (11)	0.0235 (12)	0.0017 (10)	0.0029 (10)	0.0003 (10)
C2	0.0140 (12)	0.0211 (12)	0.0222 (12)	0.0026 (10)	0.0004 (10)	−0.0013 (10)
C3	0.0174 (12)	0.0149 (11)	0.0238 (12)	−0.0002 (10)	0.0025 (10)	−0.0017 (10)
C4	0.0205 (12)	0.0186 (12)	0.0219 (12)	−0.0012 (11)	0.0074 (10)	−0.0040 (10)
O7	0.0187 (9)	0.0225 (9)	0.0298 (9)	0.0009 (7)	0.0090 (7)	0.0041 (7)
O8	0.0159 (9)	0.0255 (9)	0.0626 (14)	0.0045 (8)	0.0109 (9)	0.0130 (9)
O9	0.0228 (10)	0.0293 (9)	0.0260 (9)	0.0013 (8)	0.0082 (8)	0.0094 (7)
O10	0.0301 (10)	0.0242 (9)	0.0279 (9)	0.0003 (8)	0.0115 (8)	−0.0056 (8)
O11	0.0245 (10)	0.0228 (10)	0.0701 (15)	−0.0060 (8)	0.0082 (10)	−0.0118 (9)
O12	0.0177 (10)	0.0198 (9)	0.0682 (14)	−0.0026 (8)	0.0163 (9)	−0.0094 (9)
C5	0.0158 (12)	0.0180 (12)	0.0207 (12)	−0.0014 (10)	0.0030 (9)	−0.0023 (10)
C6	0.0169 (13)	0.0173 (11)	0.0229 (12)	0.0022 (10)	0.0065 (10)	−0.0003 (10)
C7	0.0191 (13)	0.0185 (11)	0.0234 (13)	0.0022 (9)	0.0027 (10)	−0.0011 (9)
C8	0.0158 (12)	0.0194 (13)	0.0347 (15)	−0.0002 (10)	−0.0009 (11)	−0.0013 (11)
O13	0.0290 (10)	0.0348 (10)	0.0243 (10)	−0.0056 (8)	0.0066 (8)	0.0061 (8)
O14	0.0192 (9)	0.0259 (9)	0.0342 (10)	−0.0075 (7)	0.0032 (8)	0.0052 (8)
O15	0.0215 (9)	0.0196 (8)	0.0266 (9)	0.0038 (7)	0.0076 (7)	0.0033 (7)
O16	0.0255 (10)	0.0365 (10)	0.0443 (11)	−0.0035 (9)	0.0033 (9)	−0.0258 (9)
O17	0.0320 (10)	0.0435 (11)	0.0180 (9)	−0.0012 (9)	0.0083 (7)	0.0029 (8)
O18	0.0211 (9)	0.0311 (9)	0.0218 (9)	−0.0121 (7)	0.0063 (7)	−0.0029 (7)
C9	0.0201 (13)	0.0194 (11)	0.0221 (13)	−0.0008 (10)	0.0056 (10)	−0.0045 (10)
C10	0.0175 (12)	0.0181 (11)	0.0209 (12)	−0.0016 (10)	0.0026 (10)	−0.0042 (9)
C11	0.0205 (13)	0.0163 (11)	0.0224 (12)	−0.0006 (10)	0.0024 (10)	−0.0031 (9)
C12	0.0155 (12)	0.0197 (11)	0.0182 (12)	0.0048 (10)	0.0031 (9)	−0.0012 (9)
N1	0.0229 (11)	0.0232 (10)	0.0184 (10)	−0.0039 (9)	0.0031 (8)	0.0020 (8)
C13	0.0299 (14)	0.0409 (15)	0.0245 (13)	−0.0037 (13)	0.0102 (11)	−0.0016 (12)
C14	0.0382 (18)	0.0535 (19)	0.0481 (19)	0.0074 (16)	0.0106 (15)	−0.0084 (16)
C15	0.0286 (14)	0.0263 (13)	0.0241 (13)	−0.0029 (11)	0.0056 (11)	0.0057 (10)
C16	0.0345 (16)	0.0290 (14)	0.0396 (16)	−0.0059 (12)	0.0062 (13)	0.0088 (12)
C17	0.0288 (15)	0.0314 (13)	0.0280 (14)	−0.0014 (12)	−0.0036 (11)	−0.0045 (11)
C18	0.0387 (19)	0.0378 (17)	0.055 (2)	−0.0119 (14)	−0.0069 (16)	0.0025 (15)
C19	0.0285 (15)	0.0287 (13)	0.0297 (14)	−0.0048 (12)	−0.0043 (11)	0.0093 (11)
C20	0.0393 (18)	0.0340 (16)	0.062 (2)	0.0103 (14)	0.0003 (16)	0.0008 (15)
N2	0.0307 (12)	0.0308 (11)	0.0137 (9)	0.0042 (10)	0.0030 (9)	0.0012 (9)
C21	0.0364 (16)	0.0384 (15)	0.0208 (13)	0.0009 (13)	0.0051 (12)	−0.0062 (12)
C22	0.061 (2)	0.0441 (17)	0.0474 (19)	−0.0139 (16)	0.0234 (17)	−0.0142 (15)
C23	0.0292 (16)	0.0456 (16)	0.0279 (14)	0.0083 (13)	0.0110 (12)	0.0082 (12)
C24	0.042 (2)	0.0465 (18)	0.069 (2)	−0.0022 (16)	0.0227 (18)	−0.0028 (17)
C25	0.0346 (16)	0.0313 (14)	0.0204 (13)	0.0024 (12)	0.0096 (11)	−0.0024 (11)
C26	0.0419 (18)	0.0365 (15)	0.0369 (16)	0.0082 (13)	0.0154 (14)	0.0008 (13)
C27	0.0509 (19)	0.0422 (15)	0.0169 (13)	0.0139 (14)	−0.0031 (12)	0.0046 (12)
C28	0.054 (2)	0.0522 (19)	0.0235 (14)	0.0226 (17)	0.0008 (13)	0.0018 (14)
O1W	0.0376 (13)	0.0253 (10)	0.0444 (13)	−0.0045 (9)	0.0041 (10)	0.0029 (10)

O1—C1	1.261 (3)	C14—H14B	0.9800
O2—C1	1.249 (3)	C14—H14A	0.9800
O3—C2	1.405 (3)	C15—C16	1.512 (4)
O3—H3O	0.8400	C15—H15A	0.9900
O4—C3	1.406 (3)	C15—H15B	0.9900
O4—H4O	0.8400	C16—H16C	0.9800
O5—C4	1.216 (3)	C16—H16B	0.9800
O6—C4	1.302 (3)	C16—H16A	0.9800
O6—H6O	0.8400	C17—C18	1.508 (4)
C1—C2	1.528 (3)	C17—H17A	0.9900
C2—C3	1.539 (3)	C17—H17B	0.9900
C2—H2	1.0000	C18—H18C	0.9800
C3—C4	1.519 (3)	C18—H18B	0.9800
C3—H3	1.0000	C18—H18A	0.9800
O7—C5	1.246 (3)	C19—C20	1.511 (4)
O8—C5	1.261 (3)	C19—H19A	0.9900
O9—C6	1.411 (3)	C19—H19B	0.9900
O9—H9O	0.8400	C20—H20A	0.9800
O10—C7	1.412 (3)	C20—H20B	0.9800
O10—H10O	0.8400	C20—H20C	0.9800
O11—C8	1.208 (3)	N2—C23	1.516 (3)
O12—C8	1.306 (3)	N2—C25	1.517 (3)
O12—H12O	0.8400	N2—C21	1.517 (3)
C5—C6	1.531 (3)	N2—C27	1.519 (3)
C6—C7	1.541 (3)	C21—C22	1.517 (4)
C6—H6	1.0000	C21—H21A	0.9900
C7—C8	1.517 (4)	C21—H21B	0.9900
C7—H7	1.0000	C22—H22C	0.9800
O13—C9	1.219 (3)	C22—H22B	0.9800
O14—C9	1.311 (3)	C22—H22A	0.9800
O14—H14O	0.8400	C23—C24	1.513 (5)
O15—C10	1.413 (3)	C23—H23A	0.9900
O15—H15O	0.8400	C23—H23B	0.9900
O16—C11	1.411 (3)	C24—H24C	0.9800
O16—H16O	0.8400	C24—H24B	0.9800
O17—C12	1.204 (3)	C24—H24A	0.9800
O18—C12	1.316 (3)	C25—C26	1.508 (4)
O18—H18O	0.8400	C25—H25A	0.9900
C9—C10	1.522 (3)	C25—H25B	0.9900
C10—C11	1.538 (3)	C26—H26C	0.9800
C10—H10	1.0000	C26—H26B	0.9800
C11—C12	1.520 (3)	C26—H26A	0.9800
C11—H11	1.0000	C27—C28	1.510 (4)
N1—C15	1.515 (3)	C27—H27A	0.9900
N1—C13	1.519 (3)	C27—H27B	0.9900
N1—C19	1.523 (3)	C28—H28C	0.9800
N1—C17	1.526 (3)	C28—H28B	0.9800
C13—C14	1.506 (4)	C28—H28A	0.9800
C13—H13A	0.9900	O1W—H1WA	0.83 (4)
C13—H13B	0.9900	O1W—H1WB	0.88 (5)
C14—H14C	0.9800
C2—O3—H3O	109.5	H15A—C15—H15B	107.5
C3—O4—H4O	109.5	C15—C16—H16C	109.5
C4—O6—H6O	109.5	C15—C16—H16B	109.5
O2—C1—O1	126.1 (2)	H16C—C16—H16B	109.5
O2—C1—C2	115.9 (2)	C15—C16—H16A	109.5
O1—C1—C2	117.9 (2)	H16C—C16—H16A	109.5
O3—C2—C1	113.48 (19)	H16B—C16—H16A	109.5
O3—C2—C3	110.34 (19)	C18—C17—N1	115.5 (2)
C1—C2—C3	111.38 (19)	C18—C17—H17A	108.4
O3—C2—H2	107.1	N1—C17—H17A	108.4
C1—C2—H2	107.1	C18—C17—H17B	108.4
C3—C2—H2	107.1	N1—C17—H17B	108.4
O4—C3—C4	113.41 (19)	H17A—C17—H17B	107.5
O4—C3—C2	112.41 (19)	C17—C18—H18C	109.5
C4—C3—C2	108.57 (19)	C17—C18—H18B	109.5
O4—C3—H3	107.4	H18C—C18—H18B	109.5
C4—C3—H3	107.4	C17—C18—H18A	109.5
C2—C3—H3	107.4	H18C—C18—H18A	109.5
O5—C4—O6	124.8 (2)	H18B—C18—H18A	109.5
O5—C4—C3	124.2 (2)	C20—C19—N1	115.5 (2)
O6—C4—C3	111.1 (2)	C20—C19—H19A	108.4
C6—O9—H9O	109.5	N1—C19—H19A	108.4
C7—O10—H10O	109.5	C20—C19—H19B	108.4
C8—O12—H12O	109.5	N1—C19—H19B	108.4
O7—C5—O8	124.9 (2)	H19A—C19—H19B	107.5
O7—C5—C6	119.2 (2)	C19—C20—H20A	109.5
O8—C5—C6	115.8 (2)	C19—C20—H20B	109.5
O9—C6—C5	112.13 (19)	H20A—C20—H20B	109.5
O9—C6—C7	110.67 (19)	C19—C20—H20C	109.5
C5—C6—C7	109.97 (19)	H20A—C20—H20C	109.5
O9—C6—H6	108.0	H20B—C20—H20C	109.5
C5—C6—H6	108.0	C23—N2—C25	111.3 (2)
C7—C6—H6	108.0	C23—N2—C21	106.50 (19)
O10—C7—C8	111.96 (19)	C25—N2—C21	111.1 (2)
O10—C7—C6	111.45 (19)	C23—N2—C27	110.8 (2)
C8—C7—C6	109.8 (2)	C25—N2—C27	106.34 (19)
O10—C7—H7	107.8	C21—N2—C27	110.9 (2)
C8—C7—H7	107.8	C22—C21—N2	114.8 (2)
C6—C7—H7	107.8	C22—C21—H21A	108.6
O11—C8—O12	124.3 (2)	N2—C21—H21A	108.6
O11—C8—C7	123.0 (2)	C22—C21—H21B	108.6
O12—C8—C7	112.7 (2)	N2—C21—H21B	108.6
C9—O14—H14O	109.5	H21A—C21—H21B	107.5
C10—O15—H15O	109.5	C21—C22—H22C	109.5
C11—O16—H16O	109.5	C21—C22—H22B	109.5
C12—O18—H18O	109.5	H22C—C22—H22B	109.5
O13—C9—O14	125.2 (2)	C21—C22—H22A	109.5
O13—C9—C10	120.7 (2)	H22C—C22—H22A	109.5
O14—C9—C10	114.1 (2)	H22B—C22—H22A	109.5
O15—C10—C9	114.16 (19)	C24—C23—N2	115.5 (2)
O15—C10—C11	108.28 (18)	C24—C23—H23A	108.4
C9—C10—C11	108.58 (18)	N2—C23—H23A	108.4
O15—C10—H10	108.6	C24—C23—H23B	108.4
C9—C10—H10	108.6	N2—C23—H23B	108.4
C11—C10—H10	108.6	H23A—C23—H23B	107.5
O16—C11—C12	110.6 (2)	C23—C24—H24C	109.5
O16—C11—C10	111.75 (19)	C23—C24—H24B	109.5
C12—C11—C10	110.23 (18)	H24C—C24—H24B	109.5
O16—C11—H11	108.0	C23—C24—H24A	109.5
C12—C11—H11	108.0	H24C—C24—H24A	109.5
C10—C11—H11	108.0	H24B—C24—H24A	109.5
O17—C12—O18	125.1 (2)	C26—C25—N2	115.3 (2)
O17—C12—C11	124.2 (2)	C26—C25—H25A	108.4
O18—C12—C11	110.68 (19)	N2—C25—H25A	108.4
C15—N1—C13	111.18 (19)	C26—C25—H25B	108.4
C15—N1—C19	110.43 (19)	N2—C25—H25B	108.4
C13—N1—C19	106.50 (19)	H25A—C25—H25B	107.5
C15—N1—C17	106.36 (18)	C25—C26—H26C	109.5
C13—N1—C17	111.3 (2)	C25—C26—H26B	109.5
C19—N1—C17	111.15 (19)	H26C—C26—H26B	109.5
C14—C13—N1	115.5 (2)	C25—C26—H26A	109.5
C14—C13—H13A	108.4	H26C—C26—H26A	109.5
N1—C13—H13A	108.4	H26B—C26—H26A	109.5
C14—C13—H13B	108.4	C28—C27—N2	114.6 (2)
N1—C13—H13B	108.4	C28—C27—H27A	108.6
H13A—C13—H13B	107.5	N2—C27—H27A	108.6
C13—C14—H14C	109.5	C28—C27—H27B	108.6
C13—C14—H14B	109.5	N2—C27—H27B	108.6
H14C—C14—H14B	109.5	H27A—C27—H27B	107.6
C13—C14—H14A	109.5	C27—C28—H28C	109.5
H14C—C14—H14A	109.5	C27—C28—H28B	109.5
H14B—C14—H14A	109.5	H28C—C28—H28B	109.5
C16—C15—N1	115.1 (2)	C27—C28—H28A	109.5
C16—C15—H15A	108.5	H28C—C28—H28A	109.5
N1—C15—H15A	108.5	H28B—C28—H28A	109.5
C16—C15—H15B	108.5	H1WA—O1W—H1WB	108 (4)
N1—C15—H15B	108.5
O2—C1—C2—O3	8.5 (3)	O15—C10—C11—C12	−67.9 (2)
O1—C1—C2—O3	−173.5 (2)	C9—C10—C11—C12	167.62 (19)
O2—C1—C2—C3	133.7 (2)	O16—C11—C12—O17	−10.4 (3)
O1—C1—C2—C3	−48.3 (3)	C10—C11—C12—O17	113.7 (3)
O3—C2—C3—O4	61.1 (2)	O16—C11—C12—O18	169.10 (19)
C1—C2—C3—O4	−65.8 (2)	C10—C11—C12—O18	−66.8 (2)
O3—C2—C3—C4	−65.2 (2)	C15—N1—C13—C14	60.4 (3)
C1—C2—C3—C4	167.88 (18)	C19—N1—C13—C14	−179.2 (2)
O4—C3—C4—O5	−7.3 (3)	C17—N1—C13—C14	−57.9 (3)
C2—C3—C4—O5	118.4 (2)	C13—N1—C15—C16	60.4 (3)
O4—C3—C4—O6	171.3 (2)	C19—N1—C15—C16	−57.6 (3)
C2—C3—C4—O6	−63.0 (2)	C17—N1—C15—C16	−178.3 (2)
O7—C5—C6—O9	165.8 (2)	C15—N1—C17—C18	179.2 (2)
O8—C5—C6—O9	−13.8 (3)	C13—N1—C17—C18	−59.5 (3)
O7—C5—C6—C7	−70.6 (3)	C19—N1—C17—C18	59.0 (3)
O8—C5—C6—C7	109.8 (2)	C15—N1—C19—C20	−54.8 (3)
O9—C6—C7—O10	63.3 (2)	C13—N1—C19—C20	−175.6 (2)
C5—C6—C7—O10	−61.1 (2)	C17—N1—C19—C20	63.0 (3)
O9—C6—C7—C8	−61.4 (2)	C23—N2—C21—C22	177.6 (3)
C5—C6—C7—C8	174.21 (18)	C25—N2—C21—C22	−61.1 (3)
O10—C7—C8—O11	−5.5 (4)	C27—N2—C21—C22	57.0 (3)
C6—C7—C8—O11	118.9 (3)	C25—N2—C23—C24	62.4 (3)
O10—C7—C8—O12	174.0 (2)	C21—N2—C23—C24	−176.4 (2)
C6—C7—C8—O12	−61.6 (3)	C27—N2—C23—C24	−55.7 (3)
O13—C9—C10—O15	168.0 (2)	C23—N2—C25—C26	60.9 (3)
O14—C9—C10—O15	−13.4 (3)	C21—N2—C25—C26	−57.6 (3)
O13—C9—C10—C11	−71.1 (3)	C27—N2—C25—C26	−178.4 (2)
O14—C9—C10—C11	107.5 (2)	C23—N2—C27—C28	−62.3 (3)
O15—C10—C11—O16	55.6 (2)	C25—N2—C27—C28	176.6 (3)
C9—C10—C11—O16	−68.9 (2)	C21—N2—C27—C28	55.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2	0.89 (5)	2.56 (4)	2.995 (3)	111 (3)
O1W—H1WB···O5i	0.89 (5)	2.19 (5)	3.015 (3)	155 (4)
O3—H3O···O1W	0.84	2.04	2.868 (3)	167
O3—H3O···O2	0.84	2.29	2.645 (2)	106
O4—H4O···O5	0.84	2.51	2.778 (2)	100
O4—H4O···O11	0.84	1.99	2.790 (2)	160
O6—H6O···O2ii	0.84	1.65	2.485 (2)	175
O9—H9O···O1Wii	0.84	2.25	3.077 (3)	169
O9—H9O···O8	0.84	2.23	2.635 (2)	110
O10—H10O···O5	0.84	2.05	2.848 (2)	158
O10—H10O···O11	0.84	2.43	2.720 (3)	101
O14—H14O···O7iii	0.84	1.73	2.552 (2)	164
O15—H15O···O1	0.84	2.05	2.869 (2)	166
O16—H16O···O12iii	0.84	2.27	3.054 (3)	156
O18—H18O···O1ii	0.84	1.77	2.588 (2)	165
C2—H2···O6	1.00	2.45	2.852 (3)	103
C3—H3···O1	1.00	2.54	2.890 (3)	100
C3—H3···O15	1.00	2.55	3.503 (3)	158
C7—H7···O13iv	1.00	2.52	3.396 (3)	146
C10—H10···O18	1.00	2.56	2.920 (3)	101
C13—H13A···O1Wv	0.99	2.51	3.419 (4)	152
C16—H16B···O3vi	0.98	2.46	3.378 (3)	155
C19—H19A···O3vi	0.99	2.38	3.275 (3)	150
C19—H19B···O9vi	0.99	2.37	3.294 (3)	155
C23—H23A···O17vii	0.99	2.47	3.420 (3)	161
C25—H25A···O13	0.99	2.46	3.419 (3)	164
C26—H26A···O9viii	0.98	2.56	3.482 (4)	157
C27—H27B···O18i	0.99	2.49	3.180 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2	0.89 (5)	2.56 (4)	2.995 (3)	111 (3)
O1W—H1WB⋯O5i	0.89 (5)	2.19 (5)	3.015 (3)	155 (4)
O3—H3O⋯O1W	0.84	2.04	2.868 (3)	167
O4—H4O⋯O11	0.84	1.99	2.790 (2)	160
O6—H6O⋯O2ii	0.84	1.65	2.485 (2)	175
O9—H9O⋯O1Wii	0.84	2.25	3.077 (3)	169
O10—H10O⋯O5	0.84	2.05	2.848 (2)	158
O14—H14O⋯O7iii	0.84	1.73	2.552 (2)	164
O15—H15O⋯O1	0.84	2.05	2.869 (2)	166
O16—H16O⋯O12iii	0.84	2.27	3.054 (3)	156
O18—H18O⋯O1ii	0.84	1.77	2.588 (2)	165
C3—H3⋯O15	1.00	2.55	3.503 (3)	158
C7—H7⋯O13iv	1.00	2.52	3.396 (3)	146
C13—H13A⋯O1Wv	0.99	2.51	3.419 (4)	152
C16—H16B⋯O3vi	0.98	2.46	3.378 (3)	155
C19—H19A⋯O3vi	0.99	2.38	3.275 (3)	150
C19—H19B⋯O9vi	0.99	2.37	3.294 (3)	155
C23—H23A⋯O17vii	0.99	2.47	3.420 (3)	161
C25—H25A⋯O13	0.99	2.46	3.419 (3)	164
C26—H26A⋯O9viii	0.98	2.56	3.482 (4)	157
C27—H27B⋯O18i	0.99	2.49	3.180 (3)	126

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