Channel- and layer-type anionic host structures in inclusion compounds of urea, tetraalkylammonium terephthalate/trimesate and water

New crystalline adducts of tetraalkylammonium terephthalate/trimesate with urea and water molecules result from hydrogen-bond directed assembly of complementary acceptors and donors, and the anionic host lattices are described using the graph-set notation to identify distinct hydrogen-bonding motifs and patterns. Tetra-n-butylammonium terephthalate–urea–water (1/6/2), C₄₆H₁₀₄N₁₄O₁₂ (1), triclinic, space group P1, a = 8.390 (2), b = 9.894 (2), c = 18.908 (3) Å, α = 105.06 (2), β = 94.91 (1), γ = 93.82 (2)°, Z = 1, is composed of hydrogen-bonded terephthalate–urea layers, which are intersected by urea layers to generate a three-dimensional network containing large channels for accommodation of the cations. Tetraethylammonium terephthalate–urea–water (1/­1/­5), C₂₅H₅₈N₄O₁₀ (2), triclinic, P1, a = 9.432 (1), b = 12.601 (1), c = 14.804 (1) Å, α = 79.98 (1), β = 79.20 (1), γ = 84.18 (1)°, Z = 2, has cations sandwiched between hydrogen-bonded anionic layers. Tetraethylammonium tri­mesate–urea–water (1/­2/7.5), C₃₅H₈₆N₇O_15.5 (3), triclinic, P1, a = 13.250 (1), b = 14.034 (1), c = 15.260 (1) Å, α = 72.46 (1), β = 78.32 (1), γ = 66.95 (1)°, Z = 2, manifests a layer-type structure analogous to that of (2). Tetra-n-propylammonium hydrogen trimesate–urea–water (1/2/5), C₃₅H₇₈N₆O₁₃ (4), orthorhombic, Pna2₁, a = 16.467 (3), b = 33.109 (6), c = 8.344 (1) Å, Z = 4, features hydrogen trimesate helices in a three-dimensional host architecture containing nanoscale channels each filled by a double column of cations.

Computing details

Data collection: MSC/AFC (MSC, 1988) for compd1, compd4; BioteX ver. 1.0 (MSC, 1995) for compd2; MSC bioteX (MSC, 1995) for compd3. Cell refinement: MSC/AFC (MSC, 1988) for compd1, compd4; BioteX ver. 1.0 (MSC, 1995) for compd2; MSC bioteX (MSC, 1995) for compd3. Data reduction: MSC/AFC (MSC, 1988) for compd1, compd4; BioteX ver. 1.0 (MSC, 1995) for compd2; MSC bioteX (MSC, 1995) for compd3. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: Siemens SHELXTL-PC (Siemens, 1990) for compd1, compd3; SHELXTL-PC (Siemens, 1992) for compd2; Siemens SHELXTL-PC (Siemens, 1992) for compd4.

(compd1)

Crystal data

2[N(C4H9)4]^+·C8H4O4^2^−·6(CH4N2O)·2(H2O)	Z = 1
Mr = 1045.43	F(000) = 574
Triclinic, P1	Dx = 1.155 Mg m^−3
a = 8.390 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.894 (2) Å	Cell parameters from 25 reflections
c = 18.908 (3) Å	θ = 5–15°
α = 105.06 (2)°	µ = 0.08 mm^−1
β = 94.91 (1)°	T = 293 K
γ = 93.82 (2)°	Prism, colorless
V = 1503.6 (2) Å^3	0.40 × 0.38 × 0.22 mm

Data collection

Rigaku AFC7R diffractometer	2982 reflections with I > 2σ(I)
Radiation source: Rigaku RU-200 rotating-anode generator operated at 50kV and 90mA	Rint = 0.019
Graphite monochromator	θmax = 25.1°, θmin = 2.1°
ω scan	h = −9→9
Absorption correction: ψ scan psi scan (Kopfmann & Huber, 1968)	k = 0→11
Tmin = 0.951, Tmax = 1.000	l = −22→21
5604 measured reflections	3 standard reflections every 197 reflections
5277 independent reflections	intensity decay: −0.4%

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)] = 0.050	Hydrogen site location: geom for CH, difmap for NH, OH
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.1259P] where P = (Fo^2 + 2Fc^2)/3
5277 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.32 e Å^−3
67 restraints	Δρmin = −0.31 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 > 2σ(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
C1	0.9589 (3)	0.1839 (2)	−0.03177 (12)	0.0526 (6)
O1	0.8567 (2)	0.14061 (17)	0.00384 (9)	0.0605 (4)
N1	0.9502 (3)	0.3089 (2)	−0.04676 (11)	0.0653 (6)
H1A	0.8742	0.3598	−0.0319	0.078*
H1B	1.0207	0.3380	−0.0712	0.078*
N2	1.0768 (2)	0.1074 (2)	−0.05694 (11)	0.0667 (6)
H2A	1.0841	0.0263	−0.0489	0.080*
H2B	1.1456	0.1391	−0.0813	0.080*
C2	0.7819 (3)	0.4801 (2)	0.12811 (12)	0.0482 (5)
O2	0.7496 (2)	0.48508 (17)	0.06272 (8)	0.0593 (4)
N3	0.8076 (2)	0.3595 (2)	0.14417 (10)	0.0610 (5)
H3A	0.8023	0.2829	0.1095	0.073*
H3B	0.8296	0.3583	0.1893	0.073*
N4	0.7935 (2)	0.5958 (2)	0.18342 (10)	0.0587 (5)
H4A	0.7788	0.6755	0.1748	0.070*
H4B	0.8157	0.5912	0.2279	0.070*
C3	0.5428 (3)	−0.1820 (2)	0.09938 (12)	0.0518 (6)
O3	0.66105 (19)	−0.15794 (16)	0.14637 (8)	0.0598 (4)
N5	0.5029 (3)	−0.3112 (2)	0.05539 (11)	0.0668 (6)
H5A	0.5594	−0.3787	0.0595	0.080*
H5B	0.4207	−0.3269	0.0230	0.080*
N6	0.4510 (3)	−0.0807 (2)	0.09192 (13)	0.0802 (7)
H6A	0.4734	0.0033	0.1200	0.096*
H6B	0.3694	−0.0992	0.0590	0.096*
C4	0.8915 (3)	0.4774 (2)	0.34632 (12)	0.0483 (5)
O4	0.8560 (2)	0.35831 (18)	0.30353 (9)	0.0752 (6)
O5	0.8868 (2)	0.59110 (18)	0.32875 (8)	0.0661 (5)
C5	0.9462 (2)	0.4881 (2)	0.42630 (11)	0.0416 (5)
C6	0.9891 (3)	0.6183 (2)	0.47560 (11)	0.0508 (6)
H6C	0.9820	0.6991	0.4595	0.061*
C7	0.9575 (3)	0.3699 (2)	0.45156 (12)	0.0510 (6)
H7	0.9290	0.2814	0.4193	0.061*
N7	0.3708 (2)	0.67174 (19)	0.29879 (9)	0.0488 (4)
C8	0.5364 (3)	0.7504 (2)	0.31717 (12)	0.0518 (6)
H8A	0.6153	0.6823	0.3139	0.062*
H8B	0.5536	0.8001	0.2801	0.062*
C9	0.5672 (3)	0.8544 (3)	0.39183 (13)	0.0627 (7)
H9A	0.5534	0.8065	0.4299	0.075*
H9B	0.4907	0.9247	0.3960	0.075*
C10	0.7370 (3)	0.9250 (3)	0.40214 (15)	0.0677 (7)
H10A	0.8121	0.8536	0.3933	0.081*
H10B	0.7473	0.9787	0.3663	0.081*
C11	0.7790 (4)	1.0211 (3)	0.47833 (17)	0.0883 (9)
H11A	0.8869	1.0637	0.4828	0.132*
H11B	0.7709	0.9679	0.5139	0.132*
H11C	0.7061	1.0930	0.4869	0.132*
C12	0.3359 (3)	0.5858 (2)	0.35255 (12)	0.0527 (6)
H12A	0.3353	0.6502	0.4009	0.063*
H12B	0.2285	0.5384	0.3380	0.063*
C13	0.4496 (3)	0.4770 (3)	0.35927 (14)	0.0640 (7)
H13A	0.5540	0.5231	0.3821	0.077*
H13B	0.4628	0.4183	0.3107	0.077*
C14	0.3828 (3)	0.3866 (3)	0.40587 (15)	0.0697 (7)
H14A	0.3679	0.4467	0.4539	0.084*
H14B	0.2783	0.3414	0.3826	0.084*
C15	0.4895 (4)	0.2761 (3)	0.41598 (18)	0.0903 (9)
H15A	0.4417	0.2225	0.4457	0.136*
H15B	0.5925	0.3201	0.4400	0.136*
H15C	0.5028	0.2148	0.3688	0.136*
C16	0.3691 (3)	0.5771 (3)	0.22132 (12)	0.0555 (6)
H16A	0.3910	0.6359	0.1888	0.067*
H16B	0.4565	0.5176	0.2210	0.067*
C17	0.2167 (3)	0.4846 (3)	0.18990 (14)	0.0742 (8)
H17A	0.1298	0.5423	0.1845	0.089*
H17B	0.1885	0.4294	0.2233	0.089*
C18	0.2381 (4)	0.3874 (3)	0.11571 (15)	0.0789 (8)
H18A	0.1334	0.3422	0.0928	0.095*
H18B	0.2771	0.4441	0.0849	0.095*
C19	0.3482 (4)	0.2767 (3)	0.11619 (18)	0.0984 (11)
H19A	0.3531	0.2214	0.0667	0.148*
H19B	0.3094	0.2173	0.1451	0.148*
H19C	0.4536	0.3196	0.1371	0.148*
C20	0.2394 (3)	0.7721 (2)	0.30362 (13)	0.0562 (6)
H20A	0.1364	0.7165	0.2908	0.067*
H20B	0.2428	0.8267	0.3545	0.067*
C21	0.2467 (3)	0.8726 (3)	0.25614 (16)	0.0761 (8)
H21A	0.2298	0.8209	0.2046	0.091*
H21B	0.3517	0.9251	0.2653	0.091*
C22	0.1143 (4)	0.9754 (4)	0.2745 (2)	0.1171 (13)
H22A	0.0098	0.9228	0.2593	0.176*
H22B	0.1227	1.0153	0.3274	0.176*
C23	0.1241 (6)	1.0900 (4)	0.2389 (3)	0.1418 (16)
H23A	0.0395	1.1492	0.2524	0.213*
H23B	0.1131	1.0518	0.1864	0.213*
H23C	0.2262	1.1443	0.2544	0.213*
O1W	0.6301 (3)	0.1113 (3)	0.24613 (15)	0.1206 (9)
H1WA	0.6772	0.0456	0.2198	0.181*
H1WB	0.6899	0.1880	0.2571	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0520 (13)	0.0580 (14)	0.0435 (12)	0.0010 (11)	−0.0014 (10)	0.0091 (11)
O1	0.0621 (10)	0.0588 (10)	0.0630 (10)	0.0060 (8)	0.0136 (8)	0.0187 (8)
N1	0.0669 (13)	0.0660 (13)	0.0712 (13)	0.0085 (11)	0.0121 (11)	0.0307 (11)
N2	0.0676 (13)	0.0675 (13)	0.0726 (14)	0.0124 (11)	0.0214 (11)	0.0265 (11)
C2	0.0426 (12)	0.0606 (14)	0.0441 (12)	0.0102 (10)	0.0047 (9)	0.0176 (11)
O2	0.0765 (11)	0.0651 (10)	0.0368 (8)	0.0173 (8)	−0.0021 (7)	0.0142 (7)
N3	0.0797 (14)	0.0574 (12)	0.0462 (11)	0.0082 (10)	−0.0012 (10)	0.0163 (9)
N4	0.0732 (13)	0.0650 (12)	0.0390 (10)	0.0199 (10)	0.0022 (9)	0.0136 (9)
C3	0.0505 (13)	0.0589 (14)	0.0501 (13)	0.0070 (11)	0.0080 (11)	0.0202 (11)
O3	0.0571 (10)	0.0614 (10)	0.0569 (9)	0.0069 (8)	−0.0059 (8)	0.0121 (8)
N5	0.0690 (13)	0.0671 (14)	0.0575 (12)	0.0081 (11)	−0.0119 (10)	0.0099 (11)
N6	0.0751 (15)	0.0698 (15)	0.0939 (17)	0.0186 (12)	−0.0092 (13)	0.0215 (13)
C4	0.0466 (12)	0.0563 (14)	0.0421 (11)	0.0042 (10)	0.0016 (9)	0.0147 (11)
O4	0.1118 (15)	0.0608 (11)	0.0441 (9)	0.0007 (10)	−0.0123 (9)	0.0066 (8)
O5	0.0916 (13)	0.0602 (10)	0.0459 (9)	0.0042 (9)	−0.0098 (8)	0.0194 (8)
C5	0.0384 (11)	0.0474 (12)	0.0388 (10)	0.0020 (9)	0.0034 (9)	0.0120 (9)
C6	0.0628 (14)	0.0461 (13)	0.0448 (12)	0.0015 (11)	0.0001 (10)	0.0172 (10)
C7	0.0614 (14)	0.0438 (12)	0.0442 (12)	−0.0004 (10)	−0.0034 (10)	0.0093 (10)
N7	0.0436 (10)	0.0568 (11)	0.0453 (10)	0.0014 (8)	0.0060 (8)	0.0128 (8)
C8	0.0443 (12)	0.0613 (14)	0.0491 (12)	−0.0005 (11)	0.0077 (10)	0.0141 (11)
C9	0.0571 (15)	0.0654 (15)	0.0602 (15)	−0.0039 (12)	0.0070 (12)	0.0096 (12)
C10	0.0555 (15)	0.0629 (15)	0.0801 (18)	0.0006 (12)	0.0010 (13)	0.0141 (14)
C11	0.080 (2)	0.076 (2)	0.091 (2)	−0.0095 (16)	−0.0126 (17)	0.0021 (17)
C12	0.0498 (13)	0.0617 (14)	0.0483 (12)	−0.0009 (11)	0.0099 (10)	0.0181 (11)
C13	0.0592 (15)	0.0708 (16)	0.0689 (16)	0.0108 (13)	0.0128 (12)	0.0277 (13)
C14	0.0765 (17)	0.0699 (17)	0.0675 (16)	0.0057 (14)	0.0113 (13)	0.0262 (13)
C15	0.108 (2)	0.084 (2)	0.090 (2)	0.0180 (18)	0.0130 (18)	0.0409 (17)
C16	0.0567 (14)	0.0647 (15)	0.0424 (12)	0.0030 (12)	0.0052 (10)	0.0104 (11)
C17	0.0523 (15)	0.0865 (19)	0.0685 (17)	0.0009 (14)	−0.0060 (12)	−0.0012 (15)
C18	0.0758 (18)	0.085 (2)	0.0619 (16)	0.0055 (16)	−0.0120 (14)	0.0011 (15)
C19	0.117 (3)	0.087 (2)	0.084 (2)	0.022 (2)	0.0076 (19)	0.0093 (18)
C20	0.0480 (13)	0.0592 (14)	0.0622 (14)	0.0096 (11)	0.0073 (11)	0.0161 (12)
C21	0.0707 (18)	0.0762 (18)	0.0877 (19)	0.0080 (15)	−0.0003 (15)	0.0355 (16)
C22	0.098 (3)	0.116 (3)	0.171 (4)	0.034 (2)	0.016 (2)	0.091 (3)
C23	0.155 (4)	0.116 (3)	0.159 (4)	0.036 (3)	−0.010 (3)	0.046 (3)
O1W	0.1060 (18)	0.0903 (16)	0.138 (2)	−0.0045 (13)	0.0184 (15)	−0.0177 (15)

Geometric parameters (Å, º)

C1—O1	1.253 (3)	N7—C8	1.513 (3)
C1—N2	1.331 (3)	N7—C16	1.518 (3)
C1—N1	1.344 (3)	N7—C12	1.520 (3)
C2—O2	1.257 (2)	N7—C20	1.525 (3)
C2—N4	1.326 (3)	C8—C9	1.505 (3)
C2—N3	1.332 (3)	C9—C10	1.518 (3)
C3—O3	1.240 (3)	C10—C11	1.503 (4)
C3—N6	1.333 (3)	C12—C13	1.507 (3)
C3—N5	1.334 (3)	C13—C14	1.523 (3)
C4—O4	1.245 (3)	C14—C15	1.498 (4)
C4—O5	1.255 (3)	C16—C17	1.503 (3)
C4—C5	1.517 (3)	C17—C18	1.513 (3)
C5—C7	1.380 (3)	C18—C19	1.481 (4)
C5—C6	1.383 (3)	C20—C21	1.505 (3)
C6—C7^i	1.384 (3)	C21—C22	1.556 (4)
C7—C6^i	1.384 (3)	C22—C23	1.462 (5)
O1—C1—N2	121.5 (2)	C8—N7—C12	112.06 (17)
O1—C1—N1	120.4 (2)	C16—N7—C12	110.82 (17)
N2—C1—N1	118.0 (2)	C8—N7—C20	111.54 (17)
O2—C2—N4	120.8 (2)	C16—N7—C20	111.63 (17)
O2—C2—N3	121.4 (2)	C12—N7—C20	105.40 (16)
N4—C2—N3	117.80 (19)	C9—C8—N7	115.68 (18)
O3—C3—N6	121.2 (2)	C8—C9—C10	109.6 (2)
O3—C3—N5	120.6 (2)	C11—C10—C9	111.8 (2)
N6—C3—N5	118.2 (2)	C13—C12—N7	116.72 (18)
O4—C4—O5	125.3 (2)	C12—C13—C14	109.5 (2)
O4—C4—C5	118.2 (2)	C15—C14—C13	113.1 (2)
O5—C4—C5	116.54 (19)	C17—C16—N7	116.31 (19)
C7—C5—C6	118.34 (19)	C16—C17—C18	110.2 (2)
C7—C5—C4	121.48 (19)	C19—C18—C17	116.3 (2)
C6—C5—C4	120.17 (19)	C21—C20—N7	116.7 (2)
C5—C6—C7^i	121.1 (2)	C20—C21—C22	109.0 (2)
C5—C7—C6^i	120.6 (2)	C23—C22—C21	113.8 (3)
C8—N7—C16	105.53 (16)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.27	3.045 (3)	149
N1—H1B···O2^ii	0.86	2.48	3.218 (3)	144
N2—H2A···O1^iii	0.86	2.11	2.951 (3)	164
N2—H2B···O3^iii	0.86	2.15	2.980 (3)	163
N3—H3A···O1	0.86	2.23	3.037 (3)	157
N3—H3B···O4	0.86	2.15	3.009 (2)	173
N4—H4A···O3^iv	0.86	2.14	2.962 (3)	161
N4—H4B···O5	0.86	1.95	2.805 (2)	174
N5—H5A···O2^v	0.86	2.16	3.003 (3)	165
N5—H5B···O2^vi	0.86	2.26	3.024 (2)	148
N6—H6A···O1W	0.86	2.55	3.219 (3)	135
N6—H6B···O1^vi	0.86	2.11	2.955 (3)	169
O1W—H1WA···O3	0.85	2.12	2.879 (3)	149
O1W—H1WB···O4	0.85	2.06	2.898 (3)	167

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

(compd2)

Crystal data

2[N(C2H5)4]^+·C8H4O4^2^−·CH4N2O·5(H2O)	Z = 2
Mr = 574.75	F(000) = 632
Triclinic, P1	Dx = 1.124 Mg m^−3
a = 9.432 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.601 (1) Å	Cell parameters from 95 reflections
c = 14.804 (1) Å	θ = 2–26°
α = 79.98 (1)°	µ = 0.09 mm^−1
β = 79.20 (1)°	T = 293 K
γ = 84.18 (1)°	Block, colorless
V = 1697.7 (3) Å^3	0.40 × 0.32 × 0.30 mm

Data collection

Rigaku RAXIS IIc diffractometer	4604 independent reflections
Radiation source: Rigaku RU-200 rotating-anode generator powered at 50kV and 90mA	3909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Data was collected to 0.82 Å with 79% completeness by taking 30 oscillation photos in the range of 0 – 180 °, Δφ = 6 °, exposure time 8 min. per frame. Crystal to detector distance is 78.091 mm, background level –50. scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: empirical ABSCOR (Higashi, 1995)	h = −11→11
Tmin = 0.907, Tmax = 1.060	k = −15→0
4604 measured reflections	l = −17→16

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)] = 0.069	Hydrogen site location: geom & difmap
wR(F^2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Calculated w = 1/[σ^2(Fo^2) + (0.0917P)^2 + 0.3593P] where P = (Fo^2 + 2Fc^2)/3
4604 reflections	(Δ/σ)max = 0.001
431 parameters	Δρmax = 0.23 e Å^−3
224 restraints	Δρmin = −0.15 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 > 2σ(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)
C1	0.3299 (3)	0.6145 (2)	1.47691 (19)	0.0816 (8)
O1	0.3653 (3)	0.5898 (2)	1.55620 (14)	0.1159 (8)
N1	0.3833 (3)	0.55583 (19)	1.40908 (15)	0.0849 (7)
H1A	0.4427	0.5005	1.4195	0.102*
H1B	0.3582	0.5736	1.3552	0.102*
N2	0.2381 (3)	0.6987 (2)	1.45714 (17)	0.1020 (8)
H2A	0.2013	0.7380	1.4990	0.122*
H2B	0.2154	0.7141	1.4025	0.122*
C2	0.2816 (3)	0.7086 (2)	1.19620 (17)	0.0721 (7)
O2	0.3509 (2)	0.61871 (15)	1.21006 (12)	0.0886 (6)
O3	0.2293 (3)	0.76384 (17)	1.25922 (13)	0.0978 (6)
C3	0.2553 (3)	0.75203 (19)	1.09773 (16)	0.0639 (6)
C4	0.1961 (3)	0.8573 (2)	1.07533 (17)	0.0731 (7)
H4	0.1799	0.9035	1.1194	0.088*
C5	0.1615 (3)	0.89331 (19)	0.98760 (17)	0.0711 (7)
H5	0.1238	0.9641	0.9732	0.085*
C6	0.1821 (2)	0.82532 (18)	0.92055 (16)	0.0615 (6)
C7	0.2442 (3)	0.72136 (19)	0.94203 (16)	0.0657 (6)
H7	0.2610	0.6753	0.8978	0.079*
C8	0.2816 (3)	0.68582 (19)	1.02986 (16)	0.0660 (6)
H8	0.3249	0.6166	1.0430	0.079*
C9	0.1344 (3)	0.8643 (2)	0.82690 (17)	0.0678 (6)
O4	0.1681 (2)	0.80511 (16)	0.76506 (13)	0.0949 (6)
O5	0.0618 (3)	0.95163 (16)	0.81755 (14)	0.0981 (6)
O1W	0.3839 (2)	0.45503 (19)	0.88760 (15)	0.1071 (7)
H1WA	0.3508 (4)	0.5066 (6)	0.8435 (5)	0.161*
H1WB	0.4742 (10)	0.4180 (4)	0.8626 (3)	0.161*
O2W	0.1312 (3)	0.8682 (2)	0.58192 (14)	0.1141 (8)
H2WA	0.1027 (4)	0.8677 (2)	0.6480 (7)	0.171*
H2WB	0.2349 (12)	0.8710 (2)	0.5687 (2)	0.171*
O3W	0.2538 (3)	0.59250 (17)	0.74076 (13)	0.0985 (6)
H3WA	0.2929 (5)	0.59414 (17)	0.6748 (7)	0.148*
H3WB	0.2229 (4)	0.6681 (8)	0.74520 (14)	0.148*
O4W	−0.1285 (3)	1.0364 (2)	0.70162 (19)	0.1388 (10)
H4WA	−0.1749 (6)	1.1059 (8)	0.7186 (3)	0.208*
H4WB	−0.0628 (8)	1.0107 (3)	0.7411 (5)	0.208*
O5W	0.1698 (3)	1.0568 (2)	0.44199 (19)	0.1331 (9)
H5WA	0.1734 (3)	1.0158 (5)	0.3913 (6)	0.200*
H5WB	0.1817 (3)	1.0042 (6)	0.4969 (6)	0.200*
N3	0.7398 (2)	0.69891 (18)	1.79884 (17)	0.0855 (7)
C10	0.8649 (3)	0.6965 (3)	1.7187 (2)	0.1013 (10)
H10A	0.9524	0.7071	1.7405	0.122*
H10B	0.8491	0.7573	1.6707	0.122*
C11	0.8906 (5)	0.5950 (4)	1.6748 (3)	0.1378 (15)
H11A	0.9719	0.6020	1.6248	0.207*
H11B	0.8061	0.5843	1.6509	0.207*
H11C	0.9100	0.5341	1.7208	0.207*
C12	0.7559 (3)	0.6035 (2)	1.8752 (2)	0.0909 (9)
H12A	0.6749	0.6085	1.9258	0.109*
H12B	0.7499	0.5377	1.8509	0.109*
C13	0.8946 (4)	0.5943 (3)	1.9142 (3)	0.1199 (12)
H13A	0.8954	0.5319	1.9617	0.180*
H13B	0.9005	0.6579	1.9404	0.180*
H13C	0.9758	0.5872	1.8652	0.180*
C14	0.5972 (3)	0.6887 (3)	1.7682 (3)	0.1090 (11)
H14A	0.5206	0.6870	1.8221	0.131*
H14B	0.6022	0.6203	1.7458	0.131*
C15	0.5568 (5)	0.7789 (5)	1.6925 (4)	0.188 (3)
H15A	0.4659	0.7664	1.6774	0.281*
H15B	0.6304	0.7801	1.6379	0.281*
H15C	0.5488	0.8470	1.7144	0.281*
C16	0.7410 (4)	0.8046 (3)	1.8347 (3)	0.1257 (14)
H16A	0.7296	0.8636	1.7844	0.151*
H16B	0.8352	0.8079	1.8510	0.151*
C17	0.6252 (5)	0.8229 (4)	1.9190 (4)	0.1563 (18)
H17A	0.6351	0.8914	1.9363	0.234*
H17B	0.6368	0.7664	1.9702	0.234*
H17C	0.5310	0.8224	1.9034	0.234*
N4	0.2766 (2)	0.21692 (19)	0.70160 (17)	0.0857 (7)
C18	0.1396 (4)	0.2144 (3)	0.7763 (3)	0.0881 (11)	0.75
H18A	0.0561	0.2189	0.7458	0.106*	0.75
H18B	0.1416	0.1453	0.8170	0.106*	0.75
C19	0.1195 (7)	0.3024 (6)	0.8349 (5)	0.123 (2)	0.75
H19A	0.0316	0.2943	0.8795	0.184*	0.75
H19B	0.1141	0.3714	0.7958	0.184*	0.75
H19C	0.2000	0.2977	0.8670	0.184*	0.75
C20	0.2774 (5)	0.1225 (4)	0.6522 (3)	0.1022 (13)	0.75
H20A	0.1921	0.1313	0.6230	0.123*	0.75
H20B	0.2697	0.0574	0.6982	0.123*	0.75
C21	0.4115 (9)	0.1065 (8)	0.5774 (6)	0.162 (4)	0.75
H21A	0.4024	0.0449	0.5494	0.243*	0.75
H21B	0.4966	0.0950	0.6057	0.243*	0.75
H21C	0.4193	0.1697	0.5305	0.243*	0.75
C22	0.2752 (5)	0.3257 (4)	0.6374 (4)	0.1109 (15)	0.75
H22A	0.2781	0.3821	0.6740	0.133*	0.75
H22B	0.3627	0.3270	0.5909	0.133*	0.75
C23	0.1460 (8)	0.3526 (7)	0.5875 (5)	0.151 (3)	0.75
H23A	0.1545	0.4222	0.5491	0.227*	0.75
H23B	0.0585	0.3539	0.6326	0.227*	0.75
H23C	0.1434	0.2988	0.5493	0.227*	0.75
C24	0.4084 (4)	0.2107 (3)	0.7479 (3)	0.0916 (11)	0.75
H24A	0.4032	0.2729	0.7792	0.110*	0.75
H24B	0.4948	0.2135	0.7005	0.110*	0.75
C25	0.4205 (10)	0.1050 (8)	0.8203 (7)	0.184 (5)	0.75
H25A	0.5051	0.1045	0.8478	0.275*	0.75
H25B	0.4277	0.0432	0.7895	0.275*	0.75
H25C	0.3361	0.1026	0.8681	0.275*	0.75
C18'	0.2653 (15)	0.3168 (10)	0.7423 (10)	0.114 (5)	0.25
H18C	0.2563	0.3784	0.6938	0.137*	0.25
H18D	0.3536	0.3212	0.7656	0.137*	0.25
C19'	0.135 (3)	0.323 (3)	0.822 (2)	0.235 (18)	0.25
H19D	0.1332	0.3897	0.8457	0.352*	0.25
H19E	0.1450	0.2635	0.8713	0.352*	0.25
H19F	0.0474	0.3200	0.7995	0.352*	0.25
C20'	0.1605 (15)	0.2011 (14)	0.6483 (11)	0.138 (6)	0.25
H20C	0.0693	0.1947	0.6912	0.166*	0.25
H20D	0.1842	0.1335	0.6240	0.166*	0.25
C21'	0.140 (3)	0.291 (2)	0.5676 (16)	0.183 (12)	0.25
H21D	0.0650	0.2754	0.5376	0.274*	0.25
H21E	0.2290	0.2971	0.5236	0.274*	0.25
H21F	0.1140	0.3584	0.5909	0.274*	0.25
C22'	0.4213 (13)	0.2168 (11)	0.6293 (10)	0.118 (5)	0.25
H22C	0.4129	0.2764	0.5790	0.141*	0.25
H22D	0.4988	0.2304	0.6597	0.141*	0.25
C23'	0.465 (3)	0.1135 (17)	0.5870 (19)	0.162 (10)	0.25
H23D	0.5547	0.1217	0.5441	0.243*	0.25
H23E	0.3911	0.1001	0.5546	0.243*	0.25
H23F	0.4769	0.0538	0.6356	0.243*	0.25
C24'	0.2985 (19)	0.1090 (12)	0.7676 (14)	0.178 (9)	0.25
H24C	0.3110	0.0491	0.7329	0.214*	0.25
H24D	0.2140	0.0987	0.8161	0.214*	0.25
C25'	0.4346 (14)	0.1118 (13)	0.8121 (10)	0.079 (5)	0.25
H25D	0.4471	0.0457	0.8542	0.118*	0.25
H25E	0.4223	0.1718	0.8456	0.118*	0.25
H25F	0.5184	0.1196	0.7640	0.118*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0870 (18)	0.0893 (18)	0.0653 (16)	0.0003 (15)	−0.0138 (14)	−0.0063 (13)
O1	0.1491 (19)	0.1351 (18)	0.0587 (12)	0.0478 (15)	−0.0336 (12)	−0.0186 (11)
N1	0.1042 (16)	0.0917 (15)	0.0593 (12)	0.0077 (13)	−0.0244 (11)	−0.0109 (10)
N2	0.118 (2)	0.1152 (19)	0.0681 (14)	0.0315 (16)	−0.0259 (14)	−0.0148 (12)
C2	0.0777 (16)	0.0747 (16)	0.0609 (14)	0.0040 (13)	−0.0147 (12)	−0.0050 (11)
O2	0.1096 (14)	0.0829 (12)	0.0686 (11)	0.0254 (10)	−0.0267 (10)	−0.0052 (9)
O3	0.1340 (17)	0.0919 (13)	0.0631 (11)	0.0339 (12)	−0.0249 (11)	−0.0161 (9)
C3	0.0664 (13)	0.0657 (13)	0.0565 (13)	0.0017 (11)	−0.0125 (10)	−0.0026 (10)
C4	0.0902 (17)	0.0662 (14)	0.0622 (14)	0.0056 (12)	−0.0159 (12)	−0.0121 (11)
C5	0.0858 (16)	0.0583 (13)	0.0651 (14)	0.0081 (12)	−0.0165 (12)	−0.0028 (10)
C6	0.0609 (13)	0.0620 (13)	0.0578 (13)	−0.0009 (10)	−0.0089 (10)	−0.0029 (10)
C7	0.0737 (15)	0.0617 (13)	0.0600 (13)	0.0022 (11)	−0.0111 (11)	−0.0094 (10)
C8	0.0729 (14)	0.0595 (13)	0.0630 (14)	0.0043 (11)	−0.0158 (11)	−0.0031 (10)
C9	0.0758 (15)	0.0631 (14)	0.0625 (14)	−0.0030 (12)	−0.0178 (12)	0.0003 (11)
O4	0.1289 (16)	0.0907 (13)	0.0650 (11)	0.0195 (12)	−0.0297 (11)	−0.0139 (9)
O5	0.1320 (16)	0.0783 (12)	0.0887 (13)	0.0262 (11)	−0.0512 (12)	−0.0104 (9)
O1W	0.1038 (15)	0.1138 (16)	0.0935 (14)	0.0102 (13)	−0.0104 (12)	−0.0059 (12)
O2W	0.146 (2)	0.1162 (17)	0.0694 (12)	0.0093 (14)	−0.0127 (13)	−0.0016 (11)
O3W	0.1255 (16)	0.0898 (13)	0.0734 (12)	0.0128 (12)	−0.0142 (11)	−0.0096 (9)
O4W	0.206 (3)	0.1014 (16)	0.1328 (19)	0.0447 (16)	−0.0996 (18)	−0.0406 (13)
O5W	0.172 (2)	0.1146 (18)	0.1205 (19)	−0.0522 (16)	−0.0530 (17)	0.0150 (14)
N3	0.0756 (14)	0.0790 (14)	0.0962 (16)	−0.0223 (11)	−0.0167 (12)	0.0128 (12)
C10	0.0804 (19)	0.122 (3)	0.091 (2)	−0.0264 (17)	−0.0128 (16)	0.0191 (18)
C11	0.127 (3)	0.189 (4)	0.097 (3)	−0.027 (3)	−0.005 (2)	−0.027 (3)
C12	0.099 (2)	0.0821 (18)	0.0846 (19)	−0.0156 (15)	−0.0121 (16)	0.0069 (14)
C13	0.118 (3)	0.136 (3)	0.102 (3)	−0.012 (2)	−0.037 (2)	0.013 (2)
C14	0.0764 (18)	0.119 (3)	0.124 (3)	−0.0272 (17)	−0.0220 (18)	0.020 (2)
C15	0.108 (3)	0.210 (5)	0.217 (5)	−0.036 (3)	−0.070 (3)	0.101 (4)
C16	0.109 (3)	0.081 (2)	0.183 (4)	−0.0274 (19)	−0.017 (3)	−0.008 (2)
C17	0.147 (4)	0.118 (3)	0.202 (5)	−0.014 (3)	0.005 (4)	−0.057 (3)
N4	0.0769 (14)	0.0880 (15)	0.0941 (17)	−0.0195 (12)	−0.0125 (12)	−0.0145 (12)
C18	0.072 (2)	0.090 (2)	0.103 (3)	−0.0199 (19)	−0.001 (2)	−0.025 (2)
C19	0.087 (4)	0.133 (4)	0.160 (5)	−0.018 (3)	−0.001 (3)	−0.073 (4)
C20	0.096 (3)	0.114 (3)	0.104 (3)	−0.015 (2)	−0.007 (2)	−0.045 (2)
C21	0.127 (6)	0.240 (8)	0.133 (5)	−0.014 (5)	0.000 (4)	−0.092 (5)
C22	0.104 (3)	0.105 (3)	0.118 (4)	−0.026 (3)	−0.020 (3)	0.010 (3)
C23	0.144 (5)	0.163 (6)	0.142 (5)	−0.023 (5)	−0.057 (4)	0.030 (4)
C24	0.075 (2)	0.097 (3)	0.106 (3)	−0.015 (2)	−0.018 (2)	−0.019 (2)
C25	0.170 (7)	0.171 (8)	0.206 (9)	−0.005 (6)	−0.098 (7)	0.047 (6)
C18'	0.108 (10)	0.110 (10)	0.132 (12)	−0.007 (8)	−0.020 (9)	−0.041 (9)
C19'	0.17 (3)	0.25 (3)	0.29 (3)	−0.07 (2)	0.11 (2)	−0.19 (3)
C20'	0.099 (10)	0.179 (16)	0.160 (15)	−0.046 (11)	−0.037 (10)	−0.054 (13)
C21'	0.139 (16)	0.23 (3)	0.20 (2)	−0.007 (19)	−0.095 (16)	−0.02 (2)
C22'	0.091 (9)	0.138 (12)	0.133 (12)	−0.016 (8)	−0.014 (8)	−0.049 (10)
C23'	0.14 (2)	0.181 (17)	0.19 (2)	0.007 (14)	−0.009 (15)	−0.136 (15)
C24'	0.21 (2)	0.111 (13)	0.20 (2)	−0.051 (14)	−0.030 (18)	0.043 (13)
C25'	0.065 (8)	0.084 (10)	0.087 (10)	−0.027 (7)	0.003 (8)	−0.017 (8)

Geometric parameters (Å, º)

C1—O1	1.259 (3)	C12—C13	1.512 (4)
C1—N2	1.328 (4)	C14—C15	1.524 (5)
C1—N1	1.342 (4)	C16—C17	1.530 (6)
C2—O2	1.253 (3)	N4—C18'	1.473 (10)
C2—O3	1.258 (3)	N4—C20	1.499 (5)
C2—C3	1.522 (3)	N4—C20'	1.512 (11)
C3—C8	1.387 (3)	N4—C24	1.518 (4)
C3—C4	1.396 (3)	N4—C22	1.527 (5)
C4—C5	1.387 (3)	N4—C18	1.534 (4)
C5—C6	1.395 (3)	N4—C24'	1.551 (11)
C6—C7	1.389 (3)	N4—C22'	1.569 (11)
C6—C9	1.523 (3)	C18—C19	1.500 (7)
C7—C8	1.397 (3)	C20—C21	1.539 (8)
C9—O5	1.236 (3)	C22—C23	1.521 (7)
C9—O4	1.256 (3)	C24—C25	1.566 (8)
N3—C10	1.511 (4)	C18'—C19'	1.542 (14)
N3—C12	1.517 (3)	C20'—C21'	1.524 (14)
N3—C16	1.519 (4)	C22'—C23'	1.527 (13)
N3—C14	1.521 (4)	C24'—C25'	1.554 (14)
C10—C11	1.511 (5)
O1—C1—N2	121.6 (3)	C20—N4—C24	111.9 (3)
O1—C1—N1	121.0 (3)	C20'—N4—C24	167.7 (7)
N2—C1—N1	117.4 (3)	C18'—N4—C22	61.0 (6)
O2—C2—O3	123.9 (2)	C20—N4—C22	113.4 (3)
O2—C2—C3	118.1 (2)	C20'—N4—C22	80.5 (7)
O3—C2—C3	117.9 (2)	C24—N4—C22	106.3 (3)
C8—C3—C4	118.6 (2)	C18'—N4—C18	72.8 (6)
C8—C3—C2	120.6 (2)	C20—N4—C18	106.9 (3)
C4—C3—C2	120.7 (2)	C20'—N4—C18	77.3 (7)
C5—C4—C3	120.2 (2)	C24—N4—C18	109.2 (3)
C4—C5—C6	121.2 (2)	C22—N4—C18	109.0 (3)
C7—C6—C5	118.5 (2)	C18'—N4—C24'	116.8 (11)
C7—C6—C9	121.2 (2)	C20—N4—C24'	69.3 (9)
C5—C6—C9	120.3 (2)	C20'—N4—C24'	106.3 (9)
C6—C7—C8	120.2 (2)	C24—N4—C24'	66.5 (6)
C3—C8—C7	121.2 (2)	C22—N4—C24'	172.5 (6)
O5—C9—O4	124.2 (2)	C18—N4—C24'	76.1 (8)
O5—C9—C6	117.5 (2)	C18'—N4—C22'	107.0 (7)
O4—C9—C6	118.3 (2)	C20—N4—C22'	73.6 (5)
C10—N3—C12	110.8 (2)	C20'—N4—C22'	105.2 (8)
C10—N3—C16	106.7 (2)	C24—N4—C22'	68.0 (6)
C12—N3—C16	110.6 (3)	C22—N4—C22'	73.2 (6)
C10—N3—C14	111.1 (3)	C18—N4—C22'	177.0 (6)
C12—N3—C14	105.8 (2)	C24'—N4—C22'	101.6 (10)
C16—N3—C14	111.9 (3)	C19—C18—N4	115.3 (4)
N3—C10—C11	116.3 (3)	N4—C20—C21	115.3 (5)
C13—C12—N3	115.3 (3)	C23—C22—N4	115.5 (4)
N3—C14—C15	114.9 (3)	N4—C24—C25	112.4 (4)
N3—C16—C17	115.9 (3)	N4—C18'—C19'	113.1 (14)
C18'—N4—C20	173.2 (7)	N4—C20'—C21'	114.6 (12)
C18'—N4—C20'	118.1 (9)	C23'—C22'—N4	116.1 (12)
C20—N4—C20'	55.7 (7)	N4—C24'—C25'	109.3 (11)
C18'—N4—C24	74.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.09	2.915 (3)	159
N1—H1B···O2	0.86	2.14	2.980 (3)	166
N2—H2A···O2W^ii	0.86	2.19	3.037 (4)	167
N2—H2B···O3	0.86	2.09	2.916 (3)	162
O1W—H1WA···O3W	0.91	2.02	2.914 (3)	167
O1W—H1WB···O2^iii	0.97	1.86	2.802 (3)	164
O2W—H2WA···O4	0.96	1.96	2.766 (3)	140
O3W—H3WA···O1^iv	0.97	1.77	2.742 (3)	177
O3W—H3WB···O4	0.98	1.81	2.784 (3)	174
O4W—H4WA···O3^v	0.99	1.74	2.718 (3)	171
O4W—H4WB···O5	0.93	1.80	2.727 (3)	176
O5W—H5WA···O4W^vi	0.98	1.76	2.706 (4)	163
O5W—H5WB···O2W	0.97	1.98	2.873 (3)	151

Symmetry codes: (i) −x+1, −y+1, −z+3; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) x, y, z−1; (v) −x, −y+2, −z+2; (vi) −x, −y+2, −z+1.

(compd3)

Crystal data

3[N(C2H5)4]^+·C9H3O6^3^−·2(CH4N2O)·7.5(H2O)	Z = 2
Mr = 853.11	F(000) = 938
Triclinic, P1	Dx = 1.143 Mg m^−3
a = 13.250 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.034 (1) Å	Cell parameters from 118 reflections
c = 15.260 (1) Å	θ = 2–26°
α = 72.46 (1)°	µ = 0.09 mm^−1
β = 78.32 (1)°	T = 293 K
γ = 66.95 (1)°	Block, colorless
V = 2478.1 (3) Å^3	0.60 × 0.50 × 0.40 mm

Data collection

Rigaku RAXIS IIc diffractometer	6973 independent reflections
Radiation source: Rigaku RU-200 rotating-anode generator operated at 50kV and 90mA	5849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Take 36 oscillation photos in the range of 0 – 180°, Δφ = 5°, 10 min. per frame. Background level –40. Crystal to detector distance 78.037 mm. scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: empirical ABSCOR (Higashi, 1995)	h = −16→14
Tmin = 0.863, Tmax = 1.138	k = −17→0
6973 measured reflections	l = −18→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom except N, O difmap
R[F^2 > 2σ(F^2)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.215	Calculated w = 1/[σ^2(Fo^2) + (0.0987P)^2 + 0.6009P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
6973 reflections	Δρmax = 0.45 e Å^−3
646 parameters	Δρmin = −0.40 e Å^−3
403 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (4)

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 > 2σ(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)
C1	0.8271 (2)	0.2969 (2)	0.49021 (19)	0.0695 (7)
O1	0.8354 (2)	0.3139 (2)	0.56284 (14)	0.0899 (6)
N1	0.7696 (3)	0.2378 (3)	0.48821 (19)	0.1038 (9)
H1A	0.7371	0.2104	0.5384	0.125*
H1B	0.7652	0.2272	0.4367	0.125*
N2	0.8763 (2)	0.3354 (2)	0.41004 (17)	0.0823 (7)
H2A	0.9150	0.3731	0.4079	0.099*
H2B	0.8694	0.3226	0.3603	0.099*
C2	0.9701 (5)	0.4703 (4)	−0.3393 (4)	0.1475 (19)
O2	1.0148 (2)	0.5136 (2)	−0.41606 (16)	0.0960 (7)
N3	0.8719 (3)	0.4384 (2)	−0.33695 (19)	0.0981 (9)
H3A	0.8453	0.4492	−0.3874	0.118*
H3B	0.8432	0.4097	−0.2851	0.118*
N4	1.0286 (5)	0.4406 (4)	−0.2461 (3)	0.232 (2)
H4A	1.0875	0.4537	−0.2489	0.278*
H4B	1.0007	0.4116	−0.1939	0.278*
C3	0.7876 (2)	0.2378 (2)	0.24831 (17)	0.0578 (6)
O3	0.73989 (18)	0.20044 (17)	0.32165 (13)	0.0784 (5)
O4	0.85359 (17)	0.28354 (17)	0.24381 (13)	0.0777 (5)
C4	0.7632 (2)	0.22912 (19)	0.15922 (17)	0.0553 (6)
C5	0.8084 (2)	0.2748 (2)	0.07516 (17)	0.0589 (6)
H5	0.8522	0.3134	0.0738	0.071*
C6	0.7899 (2)	0.2644 (2)	−0.00719 (17)	0.0603 (6)
C7	0.7238 (2)	0.2073 (2)	−0.00365 (18)	0.0639 (7)
H7	0.7113	0.1995	−0.0585	0.077*
C8	0.6758 (2)	0.1615 (2)	0.07857 (18)	0.0606 (6)
C9	0.6960 (2)	0.1727 (2)	0.16046 (18)	0.0591 (6)
H9	0.6644	0.1423	0.2166	0.071*
C10	0.8444 (3)	0.3111 (3)	−0.0976 (2)	0.0750 (8)
O5	0.8168 (2)	0.3094 (2)	−0.17028 (14)	0.0980 (7)
O6	0.9140 (2)	0.3491 (3)	−0.09436 (17)	0.1161 (9)
C11	0.6053 (3)	0.0991 (3)	0.0794 (2)	0.0754 (8)
O7	0.5798 (2)	0.0435 (2)	0.15605 (18)	0.1047 (7)
O8	0.5807 (2)	0.1020 (2)	0.00548 (18)	0.1164 (8)
O1W	0.8140 (2)	0.17790 (19)	−0.26933 (17)	0.0903 (7)
H1WA	0.810 (4)	0.226 (3)	−0.3275 (17)	0.135*
H1WB	0.814 (3)	0.215 (3)	−0.228 (2)	0.135*
O2W	0.3826 (2)	0.8220 (2)	0.30497 (17)	0.0941 (7)
H2WA	0.423 (3)	0.844 (4)	0.250 (2)	0.141*
H2WB	0.316 (2)	0.826 (4)	0.288 (3)	0.141*
O3W	0.5015 (2)	0.1072 (2)	−0.14886 (16)	0.0913 (7)
H3WA	0.522 (3)	0.095 (3)	−0.0898 (18)	0.137*
H3WB	0.486 (3)	0.046 (2)	−0.146 (3)	0.137*
O4W	0.5443 (2)	0.1758 (2)	0.40696 (19)	0.1004 (7)
H4WA	0.612 (2)	0.182 (4)	0.375 (3)	0.151*
H4WB	0.576 (3)	0.132 (3)	0.4632 (19)	0.151*
O5W	0.4471 (2)	0.1050 (2)	0.3081 (2)	0.1083 (8)
H5WA	0.497 (3)	0.080 (4)	0.260 (2)	0.162*
H5WB	0.490 (3)	0.111 (4)	0.347 (3)	0.162*
O6W	0.3847 (3)	0.9403 (2)	0.42127 (18)	0.1155 (9)
H6WA	0.397 (4)	0.889 (3)	0.388 (3)	0.173*
H6WB	0.396 (4)	1.001 (3)	0.379 (3)	0.173*
O7W	0.8602 (3)	0.4837 (2)	0.1508 (2)	0.1225 (10)
H7WA	0.867 (4)	0.411 (2)	0.180 (4)	0.184*
H7WB	0.922 (3)	0.472 (4)	0.105 (3)	0.184*
O8W	0.9502 (6)	0.4894 (5)	−0.0251 (5)	0.136 (2)	0.50
H8WA	0.892 (5)	0.503 (7)	0.022 (4)	0.204*	0.50
H8WB	0.937 (6)	0.435 (5)	−0.040 (7)	0.204*	0.50
N5	0.18049 (19)	0.1644 (2)	0.10684 (19)	0.0805 (8)
C12	0.2255 (4)	0.0843 (5)	0.1965 (4)	0.0967 (16)	0.70
H12A	0.2570	0.0134	0.1853	0.116*	0.70
H12B	0.2852	0.1002	0.2094	0.116*	0.70
C13	0.1462 (7)	0.0808 (7)	0.2808 (5)	0.114 (3)	0.70
H13A	0.1838	0.0286	0.3320	0.170*	0.70
H13B	0.0881	0.0619	0.2706	0.170*	0.70
H13C	0.1156	0.1497	0.2943	0.170*	0.70
C14	0.2718 (4)	0.1560 (4)	0.0339 (4)	0.0944 (16)	0.70
H14A	0.3011	0.0837	0.0261	0.113*	0.70
H14B	0.3299	0.1682	0.0537	0.113*	0.70
C15	0.2414 (9)	0.2334 (10)	−0.0592 (6)	0.140 (5)	0.70
H15A	0.3056	0.2233	−0.1029	0.210*	0.70
H15B	0.2137	0.3055	−0.0527	0.210*	0.70
H15C	0.1859	0.2204	−0.0807	0.210*	0.70
C16	0.0819 (3)	0.1555 (4)	0.0867 (3)	0.0821 (13)	0.70
H16A	0.0560	0.2098	0.0311	0.099*	0.70
H16B	0.0249	0.1708	0.1368	0.099*	0.70
C17	0.0969 (6)	0.0475 (6)	0.0733 (7)	0.115 (3)	0.70
H17A	0.0282	0.0490	0.0605	0.173*	0.70
H17B	0.1205	−0.0070	0.1284	0.173*	0.70
H17C	0.1514	0.0323	0.0224	0.173*	0.70
C18	0.1376 (4)	0.2787 (4)	0.1275 (4)	0.1000 (16)	0.70
H18A	0.1037	0.3319	0.0741	0.120*	0.70
H18B	0.0809	0.2809	0.1790	0.120*	0.70
C19	0.2264 (6)	0.3097 (6)	0.1501 (6)	0.150 (3)	0.70
H19A	0.1934	0.3794	0.1621	0.225*	0.70
H19B	0.2817	0.3107	0.0986	0.225*	0.70
H19C	0.2596	0.2586	0.2036	0.225*	0.70
C12'	0.1926 (10)	0.0540 (8)	0.0915 (10)	0.101 (4)	0.30
H12C	0.2572	0.0327	0.0486	0.121*	0.30
H12D	0.2061	0.0008	0.1499	0.121*	0.30
C13'	0.0971 (17)	0.0519 (17)	0.0561 (19)	0.184 (15)	0.30
H13D	0.1133	−0.0180	0.0480	0.276*	0.30
H13E	0.0831	0.1035	−0.0022	0.276*	0.30
H13F	0.0332	0.0690	0.0994	0.276*	0.30
C14'	0.2986 (7)	0.1427 (9)	0.1122 (10)	0.094 (4)	0.30
H14C	0.3421	0.1221	0.0572	0.113*	0.30
H14D	0.3251	0.0845	0.1654	0.113*	0.30
C15'	0.3105 (11)	0.2423 (11)	0.1204 (14)	0.130 (6)	0.30
H15D	0.3870	0.2300	0.1206	0.194*	0.30
H15E	0.2708	0.2599	0.1768	0.194*	0.30
H15F	0.2813	0.3004	0.0689	0.194*	0.30
C16'	0.0941 (9)	0.1937 (10)	0.1780 (7)	0.095 (4)	0.30
H16C	0.0257	0.2001	0.1589	0.114*	0.30
H16D	0.0861	0.2638	0.1826	0.114*	0.30
C17'	0.109 (2)	0.1182 (18)	0.2735 (11)	0.158 (12)	0.30
H17D	0.0442	0.1424	0.3144	0.237*	0.30
H17E	0.1718	0.1168	0.2965	0.237*	0.30
H17F	0.1197	0.0476	0.2700	0.237*	0.30
C18'	0.1421 (9)	0.2415 (8)	0.0131 (6)	0.083 (3)	0.30
H18C	0.0726	0.2382	0.0057	0.099*	0.30
H18D	0.1274	0.3136	0.0169	0.099*	0.30
C19'	0.217 (2)	0.224 (2)	−0.0726 (11)	0.124 (9)	0.30
H19D	0.1825	0.2753	−0.1255	0.186*	0.30
H19E	0.2332	0.1532	−0.0781	0.186*	0.30
H19F	0.2848	0.2327	−0.0692	0.186*	0.30
N6	0.49914 (19)	0.51845 (19)	0.25040 (18)	0.0740 (7)
C20	0.5034 (3)	0.4199 (3)	0.2270 (3)	0.0974 (11)
H20A	0.5211	0.3606	0.2812	0.117*
H20B	0.5631	0.4032	0.1790	0.117*
C21	0.3993 (4)	0.4272 (4)	0.1950 (4)	0.1290 (16)
H21A	0.4101	0.3608	0.1820	0.194*
H21B	0.3819	0.4839	0.1401	0.194*
H21C	0.3397	0.4414	0.2426	0.194*
C22	0.6108 (3)	0.4922 (3)	0.2813 (3)	0.0918 (10)
H22A	0.6229	0.4313	0.3343	0.110*
H22B	0.6669	0.4708	0.2321	0.110*
C23	0.6272 (3)	0.5804 (3)	0.3065 (3)	0.1139 (13)
H23A	0.7001	0.5557	0.3250	0.171*
H23B	0.5739	0.6011	0.3566	0.171*
H23C	0.6181	0.6407	0.2541	0.171*
C24	0.4079 (3)	0.5486 (3)	0.3252 (2)	0.0852 (9)
H24A	0.3380	0.5661	0.3022	0.102*
H24B	0.4075	0.6124	0.3379	0.102*
C25	0.4159 (4)	0.4636 (4)	0.4147 (3)	0.1298 (17)
H25A	0.3547	0.4892	0.4580	0.195*
H25B	0.4835	0.4471	0.4394	0.195*
H25C	0.4144	0.4004	0.4035	0.195*
C26	0.4744 (3)	0.6132 (3)	0.1683 (2)	0.0899 (10)
H26A	0.4726	0.6746	0.1862	0.108*
H26B	0.4014	0.6287	0.1523	0.108*
C27	0.5547 (4)	0.6002 (4)	0.0833 (3)	0.1324 (18)
H27A	0.5321	0.6640	0.0347	0.199*
H27B	0.5562	0.5407	0.0638	0.199*
H27C	0.6270	0.5876	0.0974	0.199*
N7	0.81725 (19)	0.84523 (18)	0.39177 (18)	0.0718 (6)
C28	0.8480 (3)	0.7496 (3)	0.4726 (2)	0.0851 (9)
H28A	0.9209	0.7374	0.4867	0.102*
H28B	0.8524	0.6874	0.4543	0.102*
C29	0.7704 (4)	0.7582 (4)	0.5591 (3)	0.1239 (16)
H29A	0.7970	0.6944	0.6069	0.186*
H29B	0.6985	0.7669	0.5470	0.186*
H29C	0.7660	0.8188	0.5786	0.186*
C30	0.8163 (3)	0.9435 (3)	0.4142 (3)	0.0926 (11)
H30A	0.7605	0.9587	0.4652	0.111*
H30B	0.7943	1.0036	0.3613	0.111*
C31	0.9242 (3)	0.9365 (3)	0.4393 (4)	0.1203 (14)
H31A	0.9152	1.0026	0.4519	0.181*
H31B	0.9799	0.9235	0.3888	0.181*
H31C	0.9458	0.8791	0.4931	0.181*
C32	0.9023 (3)	0.8170 (3)	0.3125 (2)	0.0840 (9)
H32A	0.8991	0.7544	0.3000	0.101*
H32B	0.9746	0.7974	0.3318	0.101*
C33	0.8906 (4)	0.9036 (4)	0.2234 (3)	0.1275 (16)
H33A	0.9478	0.8778	0.1774	0.191*
H33B	0.8965	0.9652	0.2339	0.191*
H33C	0.8200	0.9227	0.2024	0.191*
C34	0.7021 (3)	0.8716 (3)	0.3673 (3)	0.0964 (11)
H34A	0.6496	0.8929	0.4185	0.116*
H34B	0.6868	0.9324	0.3142	0.116*
C35	0.6830 (3)	0.7828 (4)	0.3459 (4)	0.1269 (16)
H35A	0.6087	0.8070	0.3305	0.190*
H35B	0.6944	0.7230	0.3989	0.190*
H35C	0.7335	0.7615	0.2947	0.190*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0855 (17)	0.0880 (18)	0.0514 (15)	−0.0447 (15)	−0.0080 (13)	−0.0202 (13)
O1	0.1285 (16)	0.1175 (15)	0.0548 (11)	−0.0741 (14)	−0.0057 (11)	−0.0257 (11)
N1	0.148 (2)	0.150 (2)	0.0624 (15)	−0.1070 (19)	−0.0007 (15)	−0.0285 (15)
N2	0.1063 (17)	0.1062 (18)	0.0556 (14)	−0.0608 (15)	−0.0077 (12)	−0.0183 (12)
C2	0.192 (5)	0.137 (4)	0.133 (4)	−0.076 (4)	0.007 (4)	−0.051 (3)
O2	0.1298 (17)	0.1077 (16)	0.0716 (14)	−0.0739 (14)	−0.0061 (13)	−0.0112 (12)
N3	0.155 (2)	0.1110 (19)	0.0619 (15)	−0.0879 (19)	0.0067 (16)	−0.0246 (14)
N4	0.445 (6)	0.276 (4)	0.111 (3)	−0.302 (4)	0.120 (3)	−0.100 (3)
C3	0.0703 (15)	0.0598 (13)	0.0494 (14)	−0.0278 (13)	−0.0078 (11)	−0.0143 (11)
O3	0.1106 (14)	0.0984 (13)	0.0497 (10)	−0.0642 (12)	−0.0094 (10)	−0.0133 (9)
O4	0.0984 (13)	0.1026 (13)	0.0604 (11)	−0.0615 (12)	−0.0058 (10)	−0.0262 (10)
C4	0.0627 (14)	0.0547 (13)	0.0511 (13)	−0.0201 (12)	−0.0086 (11)	−0.0155 (10)
C5	0.0628 (14)	0.0641 (14)	0.0568 (14)	−0.0261 (12)	−0.0094 (11)	−0.0174 (11)
C6	0.0658 (14)	0.0691 (15)	0.0488 (13)	−0.0232 (13)	−0.0108 (11)	−0.0157 (11)
C7	0.0731 (16)	0.0726 (16)	0.0523 (14)	−0.0246 (14)	−0.0147 (12)	−0.0199 (12)
C8	0.0667 (15)	0.0638 (14)	0.0577 (14)	−0.0235 (13)	−0.0105 (12)	−0.0201 (12)
C9	0.0680 (15)	0.0590 (14)	0.0559 (14)	−0.0256 (12)	−0.0073 (11)	−0.0169 (11)
C10	0.0867 (19)	0.091 (2)	0.0557 (16)	−0.0402 (17)	−0.0087 (14)	−0.0167 (14)
O5	0.1285 (17)	0.1420 (19)	0.0493 (11)	−0.0762 (16)	−0.0087 (11)	−0.0216 (12)
O6	0.1475 (19)	0.180 (2)	0.0665 (14)	−0.1178 (19)	−0.0017 (13)	−0.0201 (14)
C11	0.0911 (18)	0.0903 (18)	0.0682 (18)	−0.0479 (16)	−0.0083 (15)	−0.0306 (15)
O7	0.1432 (18)	0.1299 (17)	0.0852 (16)	−0.0936 (16)	0.0008 (14)	−0.0355 (14)
O8	0.1562 (19)	0.163 (2)	0.0857 (16)	−0.1060 (18)	−0.0249 (15)	−0.0339 (15)
O1W	0.1078 (15)	0.0973 (15)	0.0793 (14)	−0.0527 (13)	−0.0135 (12)	−0.0157 (12)
O2W	0.1091 (16)	0.1071 (16)	0.0828 (15)	−0.0556 (14)	−0.0137 (12)	−0.0205 (12)
O3W	0.1047 (14)	0.1138 (16)	0.0784 (14)	−0.0636 (13)	−0.0094 (12)	−0.0218 (12)
O4W	0.1008 (16)	0.1143 (18)	0.0932 (17)	−0.0478 (15)	−0.0121 (13)	−0.0207 (14)
O5W	0.1107 (18)	0.1281 (19)	0.1052 (19)	−0.0566 (16)	0.0034 (15)	−0.0452 (16)
O6W	0.155 (2)	0.124 (2)	0.0812 (17)	−0.0702 (19)	0.0069 (16)	−0.0284 (15)
O7W	0.128 (2)	0.1054 (18)	0.146 (3)	−0.0620 (17)	0.0105 (18)	−0.0357 (17)
O8W	0.198 (6)	0.133 (4)	0.116 (4)	−0.106 (4)	0.014 (4)	−0.039 (3)
N5	0.0610 (14)	0.0765 (16)	0.0929 (19)	−0.0207 (13)	−0.0096 (13)	−0.0087 (13)
C12	0.078 (3)	0.097 (3)	0.103 (4)	−0.020 (3)	−0.028 (3)	−0.010 (3)
C13	0.116 (5)	0.121 (6)	0.083 (4)	−0.024 (5)	−0.017 (4)	−0.017 (4)
C14	0.069 (3)	0.095 (3)	0.111 (4)	−0.027 (3)	0.005 (3)	−0.024 (3)
C15	0.113 (5)	0.135 (7)	0.129 (7)	−0.039 (5)	0.015 (5)	0.004 (6)
C16	0.064 (2)	0.097 (3)	0.081 (3)	−0.028 (2)	−0.014 (2)	−0.014 (2)
C17	0.127 (5)	0.119 (6)	0.118 (6)	−0.059 (5)	−0.026 (5)	−0.025 (4)
C18	0.090 (3)	0.086 (3)	0.124 (4)	−0.019 (3)	−0.017 (3)	−0.038 (3)
C19	0.160 (6)	0.139 (5)	0.196 (8)	−0.073 (5)	−0.050 (6)	−0.055 (5)
C12'	0.106 (9)	0.083 (8)	0.112 (10)	−0.027 (7)	−0.011 (7)	−0.030 (7)
C13'	0.33 (4)	0.091 (12)	0.133 (17)	−0.097 (17)	0.083 (19)	−0.063 (11)
C14'	0.062 (6)	0.088 (8)	0.126 (10)	−0.010 (6)	−0.031 (6)	−0.027 (7)
C15'	0.082 (8)	0.129 (12)	0.189 (16)	−0.035 (9)	−0.034 (9)	−0.045 (11)
C16'	0.088 (8)	0.091 (8)	0.095 (8)	−0.021 (7)	−0.007 (6)	−0.024 (6)
C17'	0.19 (3)	0.125 (17)	0.093 (13)	0.002 (16)	−0.010 (13)	−0.022 (11)
C18'	0.086 (7)	0.072 (6)	0.080 (7)	−0.023 (6)	−0.004 (5)	−0.014 (5)
C19'	0.142 (18)	0.106 (13)	0.092 (12)	−0.038 (12)	0.044 (11)	−0.022 (10)
N6	0.0701 (14)	0.0638 (13)	0.0867 (17)	−0.0209 (12)	−0.0094 (12)	−0.0191 (12)
C20	0.103 (2)	0.079 (2)	0.120 (3)	−0.0307 (19)	−0.009 (2)	−0.043 (2)
C21	0.124 (3)	0.124 (3)	0.178 (4)	−0.052 (3)	−0.021 (3)	−0.076 (3)
C22	0.078 (2)	0.087 (2)	0.111 (3)	−0.0252 (18)	−0.0222 (18)	−0.0219 (19)
C23	0.103 (3)	0.115 (3)	0.142 (4)	−0.041 (2)	−0.031 (2)	−0.041 (3)
C24	0.083 (2)	0.082 (2)	0.089 (2)	−0.0245 (17)	−0.0034 (17)	−0.0289 (17)
C25	0.152 (4)	0.129 (3)	0.095 (3)	−0.052 (3)	0.007 (3)	−0.019 (3)
C26	0.085 (2)	0.085 (2)	0.092 (2)	−0.0282 (18)	−0.0122 (18)	−0.0113 (18)
C27	0.127 (3)	0.142 (4)	0.101 (3)	−0.046 (3)	0.005 (3)	−0.004 (3)
N7	0.0650 (13)	0.0601 (13)	0.0902 (17)	−0.0164 (11)	−0.0123 (12)	−0.0230 (12)
C28	0.086 (2)	0.0695 (18)	0.092 (2)	−0.0223 (17)	−0.0079 (17)	−0.0163 (16)
C29	0.140 (4)	0.110 (3)	0.102 (3)	−0.037 (3)	0.009 (3)	−0.023 (2)
C30	0.091 (2)	0.0665 (18)	0.124 (3)	−0.0212 (17)	−0.011 (2)	−0.0370 (18)
C31	0.116 (3)	0.106 (3)	0.171 (4)	−0.046 (2)	−0.026 (3)	−0.061 (3)
C32	0.0733 (18)	0.084 (2)	0.091 (2)	−0.0221 (17)	−0.0056 (16)	−0.0255 (17)
C33	0.130 (4)	0.127 (3)	0.102 (3)	−0.038 (3)	0.000 (3)	−0.011 (3)
C34	0.0633 (18)	0.093 (2)	0.131 (3)	−0.0173 (18)	−0.0221 (19)	−0.031 (2)
C35	0.100 (3)	0.137 (3)	0.174 (4)	−0.050 (3)	−0.033 (3)	−0.056 (3)

Geometric parameters (Å, º)

C1—O1	1.235 (3)	N5—C12'	1.579 (10)
C1—N2	1.330 (4)	N5—C18	1.585 (6)
C1—N1	1.338 (4)	C12—C13	1.489 (8)
C2—O2	1.290 (6)	C14—C15	1.523 (9)
C2—N3	1.524 (6)	C16—C17	1.522 (9)
C2—N4	1.622 (8)	C18—C19	1.532 (8)
C3—O3	1.243 (3)	C12'—C13'	1.487 (14)
C3—O4	1.254 (3)	C14'—C15'	1.510 (13)
C3—C4	1.508 (4)	C16'—C17'	1.519 (13)
C4—C5	1.382 (4)	C18'—C19'	1.496 (13)
C4—C9	1.399 (4)	N6—C26	1.505 (4)
C5—C6	1.387 (4)	N6—C20	1.508 (4)
C6—C7	1.384 (4)	N6—C24	1.509 (4)
C6—C10	1.509 (4)	N6—C22	1.516 (4)
C7—C8	1.379 (4)	C20—C21	1.511 (5)
C8—C9	1.394 (4)	C22—C23	1.503 (5)
C8—C11	1.506 (4)	C24—C25	1.508 (5)
C10—O5	1.246 (4)	C26—C27	1.510 (5)
C10—O6	1.247 (4)	N7—C28	1.505 (4)
C11—O8	1.221 (4)	N7—C32	1.509 (4)
C11—O7	1.260 (4)	N7—C30	1.513 (4)
N5—C16'	1.433 (10)	N7—C34	1.520 (4)
N5—C16	1.460 (5)	C28—C29	1.505 (5)
N5—C14	1.462 (5)	C30—C31	1.513 (5)
N5—C14'	1.487 (9)	C32—C33	1.514 (5)
N5—C12	1.540 (5)	C34—C35	1.499 (5)
N5—C18'	1.551 (9)
O1—C1—N2	121.6 (3)	C14'—N5—C12'	98.6 (7)
O1—C1—N1	121.9 (3)	C18'—N5—C12'	101.2 (7)
N2—C1—N1	116.5 (3)	C16—N5—C18	103.9 (3)
O2—C2—N3	121.2 (5)	C14—N5—C18	109.8 (4)
O2—C2—N4	117.9 (5)	C12—N5—C18	105.5 (4)
N3—C2—N4	120.6 (4)	C13—C12—N5	117.2 (4)
O3—C3—O4	123.9 (2)	N5—C14—C15	114.6 (5)
O3—C3—C4	118.1 (2)	N5—C16—C17	115.3 (4)
O4—C3—C4	118.0 (2)	C19—C18—N5	114.9 (5)
C5—C4—C9	118.8 (2)	C13'—C12'—N5	116.1 (11)
C5—C4—C3	120.8 (2)	N5—C14'—C15'	109.1 (8)
C9—C4—C3	120.4 (2)	N5—C16'—C17'	116.4 (11)
C4—C5—C6	121.5 (3)	C19'—C18'—N5	118.1 (11)
C7—C6—C5	118.4 (2)	C26—N6—C20	111.1 (3)
C7—C6—C10	121.4 (2)	C26—N6—C24	106.0 (2)
C5—C6—C10	120.2 (3)	C20—N6—C24	111.0 (3)
C8—C7—C6	122.1 (2)	C26—N6—C22	111.2 (3)
C7—C8—C9	118.5 (3)	C20—N6—C22	106.4 (2)
C7—C8—C11	120.4 (2)	C24—N6—C22	111.2 (3)
C9—C8—C11	121.1 (2)	N6—C20—C21	115.8 (3)
C8—C9—C4	120.7 (2)	C23—C22—N6	116.1 (3)
O5—C10—O6	124.5 (3)	N6—C24—C25	115.0 (3)
O5—C10—C6	117.9 (3)	N6—C26—C27	115.4 (3)
O6—C10—C6	117.6 (3)	C28—N7—C32	106.2 (2)
O8—C11—O7	124.3 (3)	C28—N7—C30	110.8 (3)
O8—C11—C8	118.0 (3)	C32—N7—C30	111.3 (3)
O7—C11—C8	117.6 (3)	C28—N7—C34	111.5 (3)
C16—N5—C14	116.4 (4)	C32—N7—C34	110.8 (3)
C16'—N5—C14'	124.4 (8)	C30—N7—C34	106.3 (2)
C16—N5—C12	112.5 (3)	N7—C28—C29	115.3 (3)
C14—N5—C12	108.1 (3)	N7—C30—C31	115.8 (3)
C16'—N5—C18'	108.3 (6)	N7—C32—C33	115.8 (3)
C14'—N5—C18'	110.9 (7)	C35—C34—N7	115.4 (3)
C16'—N5—C12'	110.7 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3	0.86	2.02	2.874 (3)	174
N2—H2A···O2^i	0.86	2.18	3.025 (4)	169
N2—H2B···O4	0.86	2.08	2.941 (3)	177
N3—H3A···O1^ii	0.86	2.30	2.864 (4)	123
N3—H3B···O5	0.86	1.96	2.791 (4)	164
N4—H4A···O7W^i	0.86	2.28	2.905 (6)	130
N4—H4B···O6	0.86	1.92	2.762 (5)	167
O1W—H1WA···O1^ii	0.93 (2)	1.82 (2)	2.732 (3)	166 (4)
O1W—H1WB···O5	0.94 (2)	1.81 (2)	2.729 (4)	168 (4)
O2W—H2WA···O3W^iii	0.93 (2)	1.77 (2)	2.704 (3)	176 (5)
O2W—H2WB···O1W^iii	0.94 (2)	1.83 (2)	2.767 (3)	173 (4)
O3W—H3WA···O8	0.94 (2)	1.82 (2)	2.737 (3)	163 (4)
O3W—H3WB···O7^iv	0.95 (2)	1.84 (2)	2.760 (3)	164 (3)
O4W—H4WA···O3	0.96 (2)	1.80 (2)	2.756 (3)	175 (5)
O4W—H4WB···O6W^v	0.96 (2)	1.81 (2)	2.763 (4)	171 (4)
O5W—H5WA···O7	0.94 (2)	1.82 (2)	2.754 (4)	172 (4)
O5W—H5WB···O4W	0.94 (2)	1.87 (3)	2.759 (4)	158 (4)
O6W—H6WA···O2W	0.94 (2)	1.87 (3)	2.782 (4)	162 (4)
O6W—H6WB···O5W^vi	0.94 (2)	1.81 (2)	2.743 (4)	168 (5)
O7W—H7WA···O4	0.96 (2)	1.82 (2)	2.766 (4)	169 (5)
O7W—H7WB···O8W	0.96 (2)	1.91 (4)	2.698 (7)	138 (4)
O7W—H7WB···O8W^i	0.96 (2)	2.03 (3)	2.914 (7)	153 (5)
O8W—H8WA···O7W	0.95 (2)	1.88 (6)	2.698 (7)	143 (7)
O8W—H8WB···O6	0.95 (2)	1.79 (3)	2.725 (7)	168 (9)

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

(compd4)

Crystal data

2[N(C3H7)4]^+·C9H4O6^2^−·2(CH4N2O)·5(H2O)	F(000) = 1736
Mr = 791.03	Dx = 1.155 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 16.467 (3) Å	θ = 5–15°
b = 33.109 (8) Å	µ = 0.09 mm^−1
c = 8.344 (1) Å	T = 293 K
V = 4549.2 (6) Å^3	Plate, colorless
Z = 4	0.60 × 0.36 × 0.20 mm

Data collection

Rigaku AFC7R four-circle diffractometer	2341 reflections with I > 2σ(I)
Radiation source: Rigaku RU-200 rotating-anode generator powered at 50kV and 90mA	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω scan	h = 0→20
Absorption correction: ψ scan psi scan (Kopfmann & Huber, 1968)	k = 0→40
Tmin = 0.768, Tmax = 1.000	l = 0→10
4787 measured reflections	3 standard reflections every 197 reflections
4787 independent reflections	intensity decay: −5.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.173	Calculated w = 1/[σ^2(Fo^2) + (0.0895P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
4787 reflections	Δρmax = 0.22 e Å^−3
493 parameters	Δρmin = −0.21 e Å^−3
164 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1 (2)

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 > 2σ(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
C1	0.3088 (3)	0.62657 (15)	0.4516 (7)	0.0592 (14)
O1	0.3409 (2)	0.65642 (10)	0.5158 (7)	0.0878 (15)
N1	0.2311 (2)	0.62654 (12)	0.4015 (7)	0.0743 (16)
H1A	0.2016	0.6478	0.4134	0.089*
H1B	0.2109	0.6053	0.3576	0.089*
N2	0.3489 (3)	0.59131 (12)	0.4345 (6)	0.0691 (15)
H2A	0.3980	0.5891	0.4684	0.083*
H2B	0.3254	0.5711	0.3897	0.083*
C2	0.1808 (3)	0.73677 (14)	0.4537 (7)	0.0549 (14)
O2	0.13901 (17)	0.70569 (10)	0.4792 (5)	0.0637 (11)
N3	0.2605 (2)	0.73530 (12)	0.4476 (7)	0.0767 (16)
H3A	0.2853	0.7127	0.4613	0.092*
H3B	0.2880	0.7570	0.4300	0.092*
N4	0.1451 (2)	0.77326 (12)	0.4330 (7)	0.0713 (16)
H4A	0.0931	0.7754	0.4372	0.086*
H4B	0.1744	0.7943	0.4156	0.086*
C3	0.2170 (3)	0.51945 (13)	0.2290 (6)	0.0446 (12)
O3	0.16220 (18)	0.54375 (9)	0.2635 (5)	0.0580 (10)
O4	0.29003 (18)	0.52340 (10)	0.2625 (6)	0.0765 (13)
C4	0.1953 (2)	0.48199 (13)	0.1288 (6)	0.0400 (11)
C5	0.1189 (2)	0.47781 (12)	0.0630 (5)	0.0407 (11)
H5	0.0802	0.4979	0.0792	0.049*
C6	0.0991 (2)	0.44365 (13)	−0.0283 (6)	0.0415 (11)
C7	0.1566 (2)	0.41325 (13)	−0.0446 (6)	0.0421 (12)
H7	0.1427	0.3898	−0.0996	0.051*
C8	0.2336 (2)	0.41678 (12)	0.0185 (6)	0.0386 (11)
C9	0.2523 (3)	0.45148 (13)	0.1063 (6)	0.0430 (12)
H9	0.3038	0.4542	0.1507	0.052*
C10	0.0185 (2)	0.43844 (15)	−0.1024 (6)	0.0451 (12)
O5	−0.02213 (17)	0.47210 (9)	−0.1261 (5)	0.0591 (10)
H5A	−0.0694	0.4667	−0.1485	0.089*
O6	−0.00842 (19)	0.40568 (9)	−0.1452 (5)	0.0618 (10)
C11	0.2984 (3)	0.38448 (13)	−0.0052 (6)	0.0475 (12)
O7	0.36802 (18)	0.39065 (9)	0.0440 (5)	0.0574 (10)
O8	0.27667 (19)	0.35393 (10)	−0.0827 (6)	0.0774 (13)
O1W	0.4877 (2)	0.44860 (11)	0.0134 (6)	0.0756 (12)
H1WA	0.4451 (8)	0.4347 (3)	0.0237 (6)	0.113*
H1WB	0.4871 (2)	0.4652 (3)	0.0944 (17)	0.113*
O2W	0.45452 (19)	0.50504 (10)	0.2509 (5)	0.0710 (11)
H2WA	0.4032 (10)	0.51049 (15)	0.2618 (6)	0.106*
H2WB	0.4771 (4)	0.5192 (3)	0.3241 (15)	0.106*
O3W	0.0043 (2)	0.67805 (11)	0.3174 (6)	0.0720 (12)
H3WA	0.0512 (9)	0.68678 (19)	0.3502 (8)	0.108*
H3WB	0.0026 (2)	0.6549 (4)	0.3622 (10)	0.108*
O4W	0.5101 (2)	0.67308 (10)	0.5605 (6)	0.0698 (12)
H4WA	0.4607 (9)	0.6633 (2)	0.5485 (6)	0.105*
H4WB	0.5419 (6)	0.6551 (4)	0.5243 (9)	0.105*
O5W	−0.1609 (2)	0.69236 (12)	0.2690 (9)	0.121 (2)
H5WA	−0.1111 (10)	0.6839 (2)	0.2857 (10)	0.181*
H5WB	−0.1887 (6)	0.6762 (3)	0.3310 (15)	0.181*
N5	0.4492 (2)	0.37032 (10)	−0.4773 (5)	0.0469 (10)
C12	0.4092 (3)	0.40294 (13)	−0.3756 (6)	0.0507 (13)
H12A	0.3676	0.3904	−0.3100	0.061*
H12B	0.4498	0.4141	−0.3038	0.061*
C13	0.3709 (3)	0.43747 (15)	−0.4686 (8)	0.0728 (18)
H13A	0.4118	0.4506	−0.5340	0.087*
H13B	0.3291	0.4270	−0.5392	0.087*
C14	0.3340 (4)	0.46782 (17)	−0.3539 (10)	0.084 (2)
H14A	0.3106	0.4897	−0.4136	0.125*
H14B	0.3755	0.4781	−0.2841	0.125*
H14C	0.2926	0.4549	−0.2913	0.125*
C15	0.4848 (3)	0.34004 (14)	−0.3597 (7)	0.0567 (15)
H15A	0.5245	0.3538	−0.2934	0.068*
H15B	0.4417	0.3306	−0.2898	0.068*
C16	0.5250 (4)	0.30377 (16)	−0.4361 (8)	0.0760 (19)
H16A	0.4851	0.2885	−0.4967	0.091*
H16B	0.5670	0.3127	−0.5095	0.091*
C17	0.5618 (4)	0.27725 (18)	−0.3079 (10)	0.094 (2)
H17A	0.5868	0.2542	−0.3570	0.141*
H17B	0.5200	0.2684	−0.2357	0.141*
H17C	0.6019	0.2923	−0.2497	0.141*
C18	0.5144 (3)	0.38817 (15)	−0.5850 (6)	0.0575 (14)
H18A	0.5371	0.3666	−0.6498	0.069*
H18B	0.4889	0.4073	−0.6572	0.069*
C19	0.5832 (3)	0.40933 (17)	−0.4992 (8)	0.0756 (18)
H19A	0.5613	0.4298	−0.4282	0.091*
H19B	0.6129	0.3900	−0.4347	0.091*
C20	0.6394 (4)	0.4286 (2)	−0.6178 (10)	0.109 (3)
H20A	0.6828	0.4418	−0.5619	0.164*
H20B	0.6100	0.4481	−0.6803	0.164*
H20C	0.6613	0.4082	−0.6873	0.164*
C21	0.3877 (3)	0.35014 (15)	−0.5880 (6)	0.0545 (14)
H21A	0.3660	0.3705	−0.6596	0.065*
H21B	0.4163	0.3305	−0.6534	0.065*
C22	0.3174 (3)	0.32906 (17)	−0.5077 (8)	0.0758 (19)
H22A	0.2870	0.3483	−0.4437	0.091*
H22B	0.3376	0.3081	−0.4371	0.091*
C23	0.2622 (4)	0.3106 (2)	−0.6332 (11)	0.114 (3)
H23A	0.2180	0.2969	−0.5813	0.171*
H23B	0.2924	0.2916	−0.6964	0.171*
H23C	0.2412	0.3315	−0.7013	0.171*
N6	0.4482 (2)	0.13647 (11)	−0.6398 (5)	0.0520 (11)
C24	0.5105 (3)	0.11682 (16)	−0.5303 (7)	0.0587 (14)
H24A	0.5348	0.1377	−0.4646	0.070*
H24B	0.4822	0.0985	−0.4589	0.070*
C25	0.5779 (3)	0.09372 (19)	−0.6118 (7)	0.0754 (18)
H25A	0.5547	0.0731	−0.6808	0.091*
H25B	0.6094	0.1120	−0.6781	0.091*
C26	0.6324 (4)	0.0742 (2)	−0.4899 (9)	0.101 (2)
H26A	0.6748	0.0597	−0.5437	0.151*
H26B	0.6013	0.0558	−0.4255	0.151*
H26C	0.6558	0.0946	−0.4226	0.151*
C27	0.3857 (3)	0.15588 (17)	−0.5316 (8)	0.0664 (16)
H27A	0.3615	0.1349	−0.4662	0.080*
H27B	0.4137	0.1742	−0.4599	0.080*
C28	0.3181 (3)	0.17888 (19)	−0.6126 (9)	0.083 (2)
H28A	0.3411	0.2003	−0.6775	0.100*
H28B	0.2885	0.1608	−0.6832	0.100*
C29	0.2613 (4)	0.1965 (2)	−0.4935 (12)	0.130 (3)
H29A	0.2188	0.2107	−0.5483	0.195*
H29B	0.2903	0.2149	−0.4254	0.195*
H29C	0.2382	0.1752	−0.4298	0.195*
C30	0.4092 (3)	0.10515 (14)	−0.7490 (6)	0.0579 (14)
H30A	0.3670	0.1184	−0.8110	0.070*
H30B	0.4500	0.0956	−0.8238	0.070*
C31	0.3722 (4)	0.06882 (16)	−0.6662 (8)	0.0773 (19)
H31A	0.4134	0.0554	−0.6027	0.093*
H31B	0.3295	0.0777	−0.5944	0.093*
C32	0.3378 (4)	0.03964 (18)	−0.7861 (8)	0.0774 (19)
H32A	0.3142	0.0171	−0.7308	0.116*
H32B	0.3804	0.0303	−0.8554	0.116*
H32C	0.2968	0.0529	−0.8487	0.116*
C33	0.4877 (3)	0.16728 (14)	−0.7488 (7)	0.0575 (15)
H33A	0.4469	0.1772	−0.8228	0.069*
H33B	0.5290	0.1536	−0.8117	0.069*
C34	0.5267 (4)	0.20330 (16)	−0.6675 (8)	0.0773 (19)
H34A	0.4860	0.2180	−0.6069	0.093*
H34B	0.5681	0.1941	−0.5933	0.093*
C35	0.5642 (4)	0.23070 (19)	−0.7891 (10)	0.097 (2)
H35A	0.5884	0.2534	−0.7359	0.145*
H35B	0.5231	0.2400	−0.8619	0.145*
H35C	0.6052	0.2163	−0.8475	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (3)	0.048 (3)	0.070 (4)	0.000 (3)	−0.006 (3)	0.004 (3)
O1	0.059 (2)	0.0454 (19)	0.159 (5)	0.0001 (16)	−0.008 (3)	−0.018 (3)
N1	0.055 (2)	0.049 (2)	0.119 (5)	0.002 (2)	−0.017 (3)	−0.008 (3)
N2	0.061 (2)	0.050 (2)	0.096 (4)	0.006 (2)	−0.019 (3)	−0.022 (3)
C2	0.051 (3)	0.050 (3)	0.063 (3)	−0.008 (2)	−0.008 (3)	−0.002 (3)
O2	0.0535 (18)	0.0498 (19)	0.088 (3)	−0.0124 (16)	−0.001 (2)	0.012 (2)
N3	0.045 (2)	0.048 (2)	0.137 (5)	−0.0033 (18)	0.007 (3)	−0.006 (3)
N4	0.046 (2)	0.045 (2)	0.123 (5)	−0.0082 (18)	−0.003 (3)	0.008 (3)
C3	0.042 (2)	0.044 (3)	0.047 (3)	−0.006 (2)	0.004 (2)	−0.003 (3)
O3	0.0431 (17)	0.0436 (17)	0.087 (3)	0.0032 (15)	0.011 (2)	−0.024 (2)
O4	0.0404 (18)	0.072 (2)	0.117 (4)	0.0032 (17)	−0.008 (2)	−0.037 (3)
C4	0.037 (2)	0.041 (2)	0.043 (3)	0.0038 (19)	0.007 (2)	0.007 (2)
C5	0.039 (2)	0.040 (2)	0.043 (3)	0.006 (2)	−0.003 (2)	0.005 (2)
C6	0.035 (2)	0.043 (2)	0.046 (3)	−0.0006 (19)	0.004 (2)	−0.003 (2)
C7	0.044 (2)	0.041 (2)	0.042 (3)	0.0038 (19)	−0.003 (2)	−0.002 (2)
C8	0.042 (2)	0.037 (2)	0.036 (3)	0.0045 (18)	0.007 (2)	0.002 (2)
C9	0.034 (2)	0.054 (3)	0.041 (3)	0.005 (2)	0.000 (2)	−0.001 (3)
C10	0.035 (2)	0.055 (3)	0.045 (3)	0.001 (2)	−0.002 (2)	0.011 (3)
O5	0.0389 (16)	0.0424 (17)	0.096 (3)	0.0051 (14)	−0.018 (2)	0.004 (2)
O6	0.0521 (18)	0.0442 (19)	0.089 (3)	−0.0038 (15)	−0.015 (2)	−0.011 (2)
C11	0.048 (3)	0.043 (3)	0.051 (3)	0.005 (2)	−0.002 (3)	−0.004 (3)
O7	0.0377 (17)	0.0488 (19)	0.086 (3)	0.0050 (14)	−0.0082 (19)	−0.003 (2)
O8	0.0556 (19)	0.056 (2)	0.121 (4)	0.0157 (17)	−0.020 (2)	−0.035 (3)
O1W	0.061 (2)	0.075 (2)	0.091 (3)	−0.0076 (17)	0.017 (2)	−0.005 (3)
O2W	0.059 (2)	0.070 (2)	0.084 (3)	0.0039 (17)	0.002 (2)	−0.007 (2)
O3W	0.074 (2)	0.0478 (19)	0.094 (3)	−0.0039 (17)	−0.013 (2)	0.000 (2)
O4W	0.063 (2)	0.0491 (19)	0.097 (3)	0.0041 (17)	−0.009 (2)	0.002 (2)
O5W	0.070 (2)	0.076 (3)	0.216 (7)	−0.006 (2)	0.000 (4)	0.053 (4)
N5	0.057 (2)	0.048 (2)	0.035 (2)	−0.0024 (19)	0.006 (2)	−0.002 (2)
C12	0.056 (3)	0.043 (3)	0.053 (3)	0.000 (2)	0.010 (3)	−0.002 (3)
C13	0.085 (4)	0.060 (3)	0.074 (4)	0.013 (3)	0.014 (4)	0.013 (4)
C14	0.074 (4)	0.066 (4)	0.111 (6)	0.014 (3)	0.011 (4)	−0.006 (4)
C15	0.075 (3)	0.044 (3)	0.051 (4)	0.005 (3)	−0.002 (3)	0.010 (3)
C16	0.092 (4)	0.056 (3)	0.081 (5)	0.025 (3)	0.002 (4)	−0.008 (3)
C17	0.106 (5)	0.055 (3)	0.121 (7)	0.022 (3)	−0.002 (5)	0.014 (4)
C18	0.069 (3)	0.056 (3)	0.048 (3)	0.001 (3)	0.002 (3)	0.001 (3)
C19	0.071 (3)	0.079 (4)	0.076 (5)	−0.013 (3)	0.011 (4)	−0.012 (4)
C20	0.095 (5)	0.131 (6)	0.102 (6)	−0.035 (4)	0.002 (5)	0.015 (6)
C21	0.067 (3)	0.054 (3)	0.043 (3)	0.005 (2)	−0.007 (3)	0.000 (3)
C22	0.066 (3)	0.075 (4)	0.086 (5)	−0.018 (3)	−0.003 (4)	0.008 (4)
C23	0.093 (5)	0.111 (5)	0.138 (8)	−0.037 (4)	−0.012 (6)	0.000 (6)
N6	0.064 (2)	0.057 (2)	0.035 (2)	0.011 (2)	0.000 (2)	0.001 (2)
C24	0.065 (3)	0.066 (3)	0.045 (3)	0.009 (3)	−0.008 (3)	−0.001 (3)
C25	0.081 (4)	0.086 (4)	0.059 (4)	0.027 (3)	0.006 (4)	−0.003 (4)
C26	0.095 (4)	0.128 (6)	0.080 (5)	0.057 (4)	−0.010 (5)	−0.009 (5)
C27	0.066 (3)	0.076 (4)	0.057 (4)	0.016 (3)	0.010 (3)	0.001 (3)
C28	0.071 (4)	0.094 (4)	0.085 (5)	0.026 (3)	0.009 (4)	0.004 (4)
C29	0.112 (5)	0.129 (6)	0.148 (9)	0.050 (5)	0.034 (6)	0.032 (7)
C30	0.073 (3)	0.060 (3)	0.041 (3)	0.003 (3)	−0.005 (3)	−0.005 (3)
C31	0.098 (4)	0.069 (4)	0.065 (4)	−0.020 (3)	−0.005 (4)	0.004 (4)
C32	0.094 (4)	0.071 (4)	0.066 (5)	−0.014 (3)	0.008 (4)	−0.004 (3)
C33	0.065 (3)	0.057 (3)	0.051 (4)	0.001 (3)	0.005 (3)	0.005 (3)
C34	0.088 (4)	0.063 (3)	0.080 (5)	−0.009 (3)	−0.003 (4)	0.002 (4)
C35	0.112 (5)	0.078 (4)	0.099 (6)	−0.013 (4)	−0.019 (5)	0.013 (4)

Geometric parameters (Å, º)

C1—O1	1.243 (6)	N5—C12	1.523 (6)
C1—N1	1.346 (6)	N5—C21	1.524 (6)
C1—N2	1.349 (6)	C12—C13	1.519 (7)
C2—O2	1.256 (5)	C13—C14	1.515 (8)
C2—N3	1.315 (6)	C15—C16	1.513 (7)
C2—N4	1.355 (6)	C16—C17	1.511 (8)
C3—O4	1.242 (5)	C18—C19	1.512 (7)
C3—O3	1.243 (5)	C19—C20	1.497 (8)
C3—C4	1.538 (6)	C21—C22	1.510 (7)
C4—C5	1.380 (5)	C22—C23	1.515 (8)
C4—C9	1.391 (6)	N6—C27	1.513 (6)
C5—C6	1.402 (6)	N6—C33	1.514 (6)
C6—C7	1.389 (6)	N6—C24	1.520 (6)
C6—C10	1.473 (6)	N6—C30	1.522 (6)
C7—C8	1.378 (5)	C24—C25	1.510 (7)
C8—C9	1.397 (6)	C25—C26	1.503 (8)
C8—C11	1.523 (6)	C27—C28	1.508 (7)
C10—O6	1.225 (5)	C28—C29	1.483 (9)
C10—O5	1.315 (5)	C30—C31	1.515 (7)
C11—O7	1.235 (5)	C31—C32	1.502 (7)
C11—O8	1.253 (6)	C33—C34	1.515 (7)
N5—C18	1.520 (6)	C34—C35	1.494 (8)
N5—C15	1.521 (6)
O1—C1—N1	122.7 (5)	C18—N5—C12	111.0 (3)
O1—C1—N2	121.7 (5)	C15—N5—C12	105.9 (4)
N1—C1—N2	115.6 (5)	C18—N5—C21	106.3 (4)
O2—C2—N3	121.6 (4)	C15—N5—C21	111.0 (3)
O2—C2—N4	121.0 (4)	C12—N5—C21	111.2 (3)
N3—C2—N4	117.5 (4)	C13—C12—N5	115.4 (4)
O4—C3—O3	125.7 (4)	C14—C13—C12	110.1 (5)
O4—C3—C4	115.6 (4)	C16—C15—N5	114.8 (5)
O3—C3—C4	118.6 (4)	C17—C16—C15	109.8 (5)
C5—C4—C9	119.3 (4)	C19—C18—N5	115.5 (4)
C5—C4—C3	120.6 (4)	C20—C19—C18	110.3 (5)
C9—C4—C3	120.1 (4)	C22—C21—N5	116.3 (4)
C4—C5—C6	120.6 (4)	C21—C22—C23	109.9 (5)
C7—C6—C5	118.6 (4)	C27—N6—C33	111.4 (4)
C7—C6—C10	119.2 (4)	C27—N6—C24	106.4 (4)
C5—C6—C10	122.1 (4)	C33—N6—C24	111.1 (4)
C8—C7—C6	122.0 (4)	C27—N6—C30	111.0 (4)
C7—C8—C9	118.2 (4)	C33—N6—C30	106.3 (4)
C7—C8—C11	122.4 (4)	C24—N6—C30	110.7 (4)
C9—C8—C11	119.4 (4)	C25—C24—N6	116.2 (5)
C4—C9—C8	121.3 (4)	C26—C25—C24	110.6 (5)
O6—C10—O5	121.5 (4)	C28—C27—N6	116.7 (5)
O6—C10—C6	123.5 (4)	C29—C28—C27	111.3 (6)
O5—C10—C6	115.0 (4)	C31—C30—N6	116.0 (4)
O7—C11—O8	124.8 (4)	C32—C31—C30	111.0 (5)
O7—C11—C8	119.4 (4)	N6—C33—C34	116.3 (5)
O8—C11—C8	115.7 (4)	C35—C34—C33	110.4 (5)
C18—N5—C15	111.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.25	3.096 (5)	170
N1—H1B···O3	0.86	2.33	3.182 (5)	174
N2—H2A···O1W^i	0.86	2.29	3.070 (5)	151
N2—H2B···O4	0.86	1.99	2.839 (6)	169
N3—H3A···O1	0.86	2.13	2.983 (5)	175
N3—H3B···O5W^ii	0.86	2.31	3.103 (7)	154
N4—H4A···O4W^iii	0.86	2.42	3.038 (6)	130
N4—H4B···O8^iv	0.86	2.13	2.968 (5)	164
O5—H5A···O3^v	0.82	1.73	2.539 (4)	168
O1W—H1WA···O7	0.84	1.94	2.762 (5)	164
O1W—H1WB···O2W	0.87	1.93	2.778 (6)	163
O2W—H2WA···O4	0.87	1.91	2.778 (4)	174
O2W—H2WB···O1W^i	0.86	1.99	2.839 (6)	171
O3W—H3WA···O2	0.87	1.91	2.753 (5)	164
O3W—H3WB···O6^vi	0.85	2.01	2.791 (5)	152
O4W—H4WA···O1	0.88	2.00	2.864 (5)	165
O4W—H4WB···O7^i	0.85	2.13	2.915 (4)	155
O5W—H5WA···O3W	0.88	1.93	2.791 (5)	167
O5W—H5WB···O8^vi	0.87	1.90	2.741 (6)	161

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x+1/2, −y+3/2, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1/2, y+1/2, z+1/2; (v) −x, −y+1, z−1/2; (vi) −x, −y+1, z+1/2.