2-[3-(1H-Benzimidazol-2-yl)prop-yl]-1H-benzimidazol-3-ium 3,5-dicarb-oxy-benzoate-benzene-1,3,5-tricarb-oxy-lic acid-water (1/1/1).

The title compound, C(17)H(17)N(4) (+)·C(9)H(5)O(6) (-)·C(9)H(6)O(6)·H(2)O, contains a protonated 2,2'-(1,3-propanedi-yl)bis-(1H-benzimidazole) cation, a deprotonated benzene-1,3,5-tricarb-oxy-lic acid anion, a neutral benzene-1,3,5-tricarb-oxy-lic acid mol-ecule and a water mol-ecule, which are linked together through N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds into almost double sheets parallel to (4). These hydrogen-bonded sheets are packed in the crystal with the formation of centrosymmetric voids of 25.5 Å(3), which are filled by the water mol-ecules.

Related literature

For the coordination chemistry of bis-benzimidazoles, see: Sun et al. (2010 ▶). For the clinical applications of the n class="Chemical">benzimidazole ring system, see Harrell et al. (2004 ▶). For novel proton-transfer compounds, see Aghabozorg et al. (2008 ▶). For applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008 ▶).

Experimental

Crystal data

C17H17N4 +·C9H5O6 −·C9H6O6·H2O

M = 714.63

Triclinic,

a = 8.7711 (3) Å

b = 10.8389 (6) Å

c = 17.2999 (9) Å

α = 81.520 (5)°

β = 84.131 (4)°

γ = 86.998 (4)°

V = 1617.02 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.4 × 0.32 × 0.2 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.977

9922 measured reflections

5657 independent reflections

3630 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.081

S = 1.07

5657 reflections

469 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039139/pb2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039139/pb2041Isup2.hkl

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

C17H17N4+·C9H5O6−·C9H6O6·H2O	Z = 2
Mr = 714.63	F(000) = 744
Triclinic, P1	Dx = 1.468 Mg m−3
a = 8.7711 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8389 (6) Å	Cell parameters from 165 reflections
c = 17.2999 (9) Å	θ = 2.8–23.6°
α = 81.520 (5)°	µ = 0.11 mm−1
β = 84.131 (4)°	T = 293 K
γ = 86.998 (4)°	Block, colorless
V = 1617.02 (13) Å3	0.4 × 0.32 × 0.2 mm

Bruker APEX CCD area-detector diffractometer	5657 independent reflections
Radiation source: fine-focus sealed tube	3630 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.957, Tmax = 0.977	k = −12→12
9922 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3
5657 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.9366 (2)	0.70532 (19)	0.12984 (12)	0.0472 (5)
H221	0.8725	0.6395	0.1302	0.057*
C2	0.9969 (2)	0.7728 (2)	0.06116 (13)	0.0597 (6)
H222	0.9733	0.7522	0.0136	0.072*
C3	1.0926 (2)	0.8712 (2)	0.06101 (13)	0.0651 (7)
H223	1.1301	0.9150	0.0131	0.078*
C4	1.1335 (2)	0.9060 (2)	0.12862 (13)	0.0542 (6)
H224	1.1979	0.9716	0.1281	0.065*
C5	1.07310 (18)	0.83745 (17)	0.19804 (11)	0.0372 (5)
C6	0.97641 (18)	0.74056 (16)	0.19828 (11)	0.0341 (4)
C7	0.99913 (18)	0.76278 (17)	0.32189 (11)	0.0355 (4)
C8	0.9711 (2)	0.74754 (18)	0.40866 (11)	0.0433 (5)
H8A	1.0687	0.7459	0.4307	0.052*
H8B	0.9248	0.6679	0.4271	0.052*
C9	0.8672 (2)	0.85092 (18)	0.43867 (11)	0.0428 (5)
H9A	0.9056	0.9307	0.4135	0.051*
H9B	0.8744	0.8465	0.4946	0.051*
C10	0.6983 (2)	0.8473 (2)	0.42501 (10)	0.0458 (5)
H10A	0.6598	0.7672	0.4496	0.055*
H10B	0.6412	0.9114	0.4508	0.055*
C11	0.66781 (17)	0.86607 (16)	0.34136 (10)	0.0325 (4)
C12	0.57954 (18)	0.83069 (16)	0.23153 (10)	0.0332 (4)
C13	0.5143 (2)	0.7843 (2)	0.17270 (12)	0.0523 (6)
H13	0.4556	0.7137	0.1832	0.063*
C14	0.5407 (2)	0.8473 (2)	0.09827 (13)	0.0579 (6)
H14	0.4997	0.8184	0.0571	0.069*
C15	0.6273 (2)	0.9538 (2)	0.08258 (11)	0.0501 (5)
H15	0.6404	0.9955	0.0315	0.060*
C16	0.69382 (19)	0.99856 (17)	0.14092 (10)	0.0376 (5)
H16	0.7530	1.0689	0.1302	0.045*
C17	0.66929 (17)	0.93482 (15)	0.21629 (10)	0.0278 (4)
C18	0.46437 (16)	0.20168 (15)	0.29690 (9)	0.0248 (4)
C19	0.49709 (17)	0.24146 (15)	0.21723 (9)	0.0283 (4)
H19	0.4573	0.2003	0.1807	0.034*
C20	0.58961 (18)	0.34311 (16)	0.19206 (9)	0.0295 (4)
C21	0.64414 (18)	0.40664 (16)	0.24701 (9)	0.0303 (4)
H21	0.7039	0.4756	0.2300	0.036*
C22	0.61089 (17)	0.36895 (15)	0.32672 (9)	0.0260 (4)
C23	0.52217 (17)	0.26558 (15)	0.35086 (9)	0.0273 (4)
H23	0.5009	0.2384	0.4042	0.033*
C24	0.37076 (18)	0.08932 (16)	0.32472 (10)	0.0288 (4)
C25	0.6362 (2)	0.38696 (18)	0.10842 (10)	0.0380 (5)
C26	0.67101 (18)	0.43956 (16)	0.38498 (10)	0.0298 (4)
C27	0.18279 (17)	0.44108 (16)	0.18951 (9)	0.0294 (4)
C28	0.08562 (18)	0.34199 (16)	0.21251 (10)	0.0315 (4)
H28	0.0461	0.3032	0.1748	0.038*
C29	0.04780 (17)	0.30111 (15)	0.29153 (9)	0.0278 (4)
C30	0.10540 (17)	0.36020 (15)	0.34742 (9)	0.0282 (4)
H30	0.0790	0.3333	0.4004	0.034*
C31	0.20262 (17)	0.45961 (15)	0.32504 (9)	0.0248 (4)
C32	0.23957 (17)	0.49858 (15)	0.24616 (10)	0.0294 (4)
H32	0.3041	0.5650	0.2307	0.035*
C33	0.2313 (2)	0.48724 (17)	0.10617 (10)	0.0380 (5)
C34	−0.05308 (18)	0.19177 (16)	0.31858 (10)	0.0325 (4)
C35	0.27119 (17)	0.52423 (16)	0.38307 (10)	0.0287 (4)
N1	0.93470 (15)	0.69651 (13)	0.27654 (8)	0.0348 (4)
H1A	0.8758	0.6353	0.2931	0.042*
N2	1.08535 (15)	0.84712 (14)	0.27610 (9)	0.0402 (4)
H2A	1.1402	0.8996	0.2925	0.048*
N3	0.72286 (14)	0.95552 (13)	0.28622 (8)	0.0305 (3)
N4	0.57988 (15)	0.79119 (14)	0.31099 (9)	0.0375 (4)
H4A	0.5316	0.7288	0.3369	0.045*
O1	0.16654 (16)	0.43594 (14)	0.05506 (7)	0.0646 (5)
H1	0.1992	0.4662	0.0106	0.097*
O2	0.32635 (14)	0.56827 (13)	0.08772 (7)	0.0491 (4)
O3	0.34628 (14)	0.61690 (12)	0.36169 (7)	0.0446 (3)
O4	0.24293 (14)	0.47490 (11)	0.45530 (7)	0.0460 (4)
H4	0.2837	0.5149	0.4837	0.069*
O5	−0.08461 (16)	0.15746 (13)	0.38823 (7)	0.0574 (4)
O6	−0.09809 (13)	0.14016 (12)	0.26303 (7)	0.0464 (4)
H6	−0.1521	0.0816	0.2819	0.070*
O7	0.37661 (14)	0.05198 (12)	0.40002 (7)	0.0461 (4)
H7	0.3245	−0.0096	0.4136	0.069*
O8	0.30023 (13)	0.03803 (12)	0.28260 (7)	0.0425 (3)
O9	0.57854 (15)	0.32907 (13)	0.05788 (7)	0.0555 (4)
H9	0.6104	0.3591	0.0132	0.083*
O10	0.72506 (17)	0.47175 (14)	0.08869 (7)	0.0657 (5)
O11	0.74251 (14)	0.53540 (12)	0.36033 (7)	0.0474 (4)
O12	0.64331 (14)	0.39760 (11)	0.45685 (7)	0.0428 (3)
O1W	0.27197 (15)	0.84782 (13)	0.47477 (8)	0.0601 (4)
H2	0.2094	0.8558	0.5152	0.090*
H3	0.3126	0.7750	0.4838	0.090*

	U11	U22	U33	U12	U13	U23
C1	0.0492 (11)	0.0476 (13)	0.0471 (13)	−0.0132 (10)	0.0003 (10)	−0.0137 (11)
C2	0.0618 (13)	0.0745 (17)	0.0432 (13)	−0.0145 (12)	0.0032 (11)	−0.0119 (12)
C3	0.0638 (14)	0.0800 (19)	0.0451 (14)	−0.0162 (13)	0.0106 (12)	0.0061 (13)
C4	0.0456 (12)	0.0538 (15)	0.0588 (15)	−0.0215 (10)	0.0096 (11)	0.0035 (12)
C5	0.0306 (9)	0.0390 (12)	0.0417 (12)	−0.0072 (8)	−0.0007 (8)	−0.0050 (9)
C6	0.0307 (9)	0.0310 (11)	0.0399 (11)	−0.0049 (8)	0.0011 (8)	−0.0046 (9)
C7	0.0315 (9)	0.0315 (11)	0.0436 (12)	−0.0020 (8)	−0.0067 (9)	−0.0036 (9)
C8	0.0480 (11)	0.0414 (12)	0.0416 (12)	−0.0058 (9)	−0.0133 (9)	−0.0020 (10)
C9	0.0619 (12)	0.0398 (12)	0.0281 (10)	−0.0050 (9)	−0.0125 (9)	−0.0035 (9)
C10	0.0516 (12)	0.0543 (14)	0.0297 (11)	−0.0072 (10)	0.0017 (9)	−0.0022 (10)
C11	0.0299 (9)	0.0319 (11)	0.0340 (10)	−0.0047 (8)	0.0019 (8)	−0.0018 (9)
C12	0.0310 (9)	0.0316 (11)	0.0363 (11)	−0.0096 (8)	−0.0026 (8)	−0.0001 (9)
C13	0.0524 (12)	0.0532 (14)	0.0553 (14)	−0.0302 (10)	−0.0108 (11)	−0.0065 (12)
C14	0.0576 (13)	0.0755 (17)	0.0466 (14)	−0.0257 (12)	−0.0172 (11)	−0.0122 (12)
C15	0.0509 (11)	0.0655 (15)	0.0343 (11)	−0.0164 (11)	−0.0110 (10)	0.0019 (11)
C16	0.0383 (10)	0.0351 (11)	0.0385 (11)	−0.0128 (8)	−0.0038 (9)	0.0022 (9)
C17	0.0280 (9)	0.0264 (10)	0.0296 (10)	−0.0052 (7)	−0.0048 (8)	−0.0030 (8)
C18	0.0283 (9)	0.0249 (10)	0.0211 (9)	−0.0041 (7)	−0.0012 (7)	−0.0029 (7)
C19	0.0336 (9)	0.0290 (10)	0.0243 (10)	−0.0061 (7)	−0.0041 (7)	−0.0080 (8)
C20	0.0372 (9)	0.0306 (10)	0.0208 (9)	−0.0097 (8)	−0.0005 (8)	−0.0026 (8)
C21	0.0360 (9)	0.0295 (10)	0.0251 (10)	−0.0127 (8)	−0.0005 (8)	−0.0007 (8)
C22	0.0310 (9)	0.0263 (10)	0.0213 (9)	−0.0068 (7)	−0.0019 (7)	−0.0033 (8)
C23	0.0334 (9)	0.0280 (10)	0.0203 (9)	−0.0058 (7)	−0.0021 (7)	−0.0017 (8)
C24	0.0326 (9)	0.0288 (10)	0.0251 (10)	−0.0064 (8)	0.0020 (8)	−0.0058 (8)
C25	0.0524 (11)	0.0419 (12)	0.0214 (10)	−0.0198 (9)	−0.0023 (9)	−0.0046 (9)
C26	0.0371 (9)	0.0282 (11)	0.0249 (10)	−0.0097 (8)	−0.0030 (8)	−0.0036 (8)
C27	0.0352 (9)	0.0312 (11)	0.0215 (9)	−0.0090 (8)	−0.0015 (8)	−0.0009 (8)
C28	0.0362 (9)	0.0338 (11)	0.0262 (10)	−0.0100 (8)	−0.0049 (8)	−0.0061 (8)
C29	0.0314 (9)	0.0278 (10)	0.0240 (9)	−0.0078 (7)	−0.0036 (7)	−0.0005 (8)
C30	0.0335 (9)	0.0283 (10)	0.0219 (9)	−0.0067 (7)	−0.0011 (7)	0.0003 (8)
C31	0.0289 (8)	0.0228 (10)	0.0229 (9)	−0.0049 (7)	−0.0030 (7)	−0.0026 (7)
C32	0.0348 (9)	0.0261 (10)	0.0267 (10)	−0.0121 (8)	−0.0005 (8)	0.0008 (8)
C33	0.0493 (11)	0.0399 (12)	0.0260 (10)	−0.0186 (9)	0.0004 (9)	−0.0050 (9)
C34	0.0348 (10)	0.0315 (11)	0.0327 (12)	−0.0121 (8)	−0.0051 (8)	−0.0041 (9)
C35	0.0325 (9)	0.0283 (10)	0.0252 (10)	−0.0069 (8)	−0.0006 (8)	−0.0029 (8)
N1	0.0359 (8)	0.0276 (9)	0.0409 (10)	−0.0117 (7)	−0.0010 (7)	−0.0031 (7)
N2	0.0348 (8)	0.0367 (10)	0.0515 (11)	−0.0159 (7)	−0.0061 (7)	−0.0071 (8)
N3	0.0339 (8)	0.0300 (9)	0.0275 (8)	−0.0087 (6)	−0.0005 (6)	−0.0022 (7)
N4	0.0376 (8)	0.0312 (9)	0.0417 (10)	−0.0166 (7)	0.0004 (7)	0.0035 (7)
O1	0.0948 (11)	0.0814 (11)	0.0217 (7)	−0.0564 (9)	−0.0007 (7)	−0.0055 (7)
O2	0.0662 (8)	0.0569 (9)	0.0247 (7)	−0.0361 (7)	0.0015 (6)	0.0000 (6)
O3	0.0600 (8)	0.0431 (8)	0.0326 (7)	−0.0306 (7)	−0.0048 (6)	−0.0016 (6)
O4	0.0741 (9)	0.0448 (9)	0.0225 (7)	−0.0326 (7)	−0.0075 (6)	−0.0034 (6)
O5	0.0845 (10)	0.0606 (10)	0.0279 (8)	−0.0454 (8)	0.0000 (7)	0.0023 (7)
O6	0.0582 (8)	0.0465 (9)	0.0372 (8)	−0.0322 (7)	−0.0033 (6)	−0.0048 (7)
O7	0.0704 (9)	0.0426 (8)	0.0260 (7)	−0.0324 (7)	−0.0022 (6)	0.0016 (6)
O8	0.0525 (7)	0.0419 (8)	0.0363 (7)	−0.0251 (6)	−0.0087 (6)	−0.0050 (6)
O9	0.0903 (10)	0.0597 (10)	0.0190 (7)	−0.0410 (8)	−0.0007 (7)	−0.0041 (7)
O10	0.0969 (11)	0.0798 (11)	0.0235 (7)	−0.0626 (9)	0.0040 (7)	−0.0039 (7)
O11	0.0700 (9)	0.0423 (8)	0.0329 (7)	−0.0348 (7)	−0.0027 (6)	−0.0049 (6)
O12	0.0710 (8)	0.0401 (8)	0.0200 (7)	−0.0265 (7)	−0.0052 (6)	−0.0040 (6)
O1W	0.0641 (8)	0.0412 (9)	0.0669 (10)	−0.0139 (7)	0.0056 (7)	0.0145 (7)

C1—C2	1.372 (3)	C19—H19	0.9300
C1—C6	1.379 (2)	C20—C21	1.388 (2)
C1—H221	0.9300	C20—C25	1.478 (2)
C2—C3	1.391 (3)	C21—C22	1.385 (2)
C2—H222	0.9300	C21—H21	0.9300
C3—C4	1.367 (3)	C22—C23	1.386 (2)
C3—H223	0.9300	C22—C26	1.503 (2)
C4—C5	1.386 (3)	C23—H23	0.9300
C4—H224	0.9300	C24—O8	1.2127 (19)
C5—N2	1.385 (2)	C24—O7	1.311 (2)
C5—C6	1.383 (2)	C25—O10	1.2232 (19)
C6—N1	1.386 (2)	C25—O9	1.304 (2)
C7—N1	1.323 (2)	C26—O11	1.2399 (19)
C7—N2	1.331 (2)	C26—O12	1.2628 (19)
C7—C8	1.482 (3)	C27—C32	1.382 (2)
C8—C9	1.524 (2)	C27—C28	1.392 (2)
C8—H8A	0.9700	C27—C33	1.481 (2)
C8—H8B	0.9700	C28—C29	1.385 (2)
C9—C10	1.528 (2)	C28—H28	0.9300
C9—H9A	0.9700	C29—C30	1.384 (2)
C9—H9B	0.9700	C29—C34	1.506 (2)
C10—C11	1.481 (2)	C30—C31	1.394 (2)
C10—H10A	0.9700	C30—H30	0.9300
C10—H10B	0.9700	C31—C32	1.378 (2)
C11—N3	1.329 (2)	C31—C35	1.495 (2)
C11—N4	1.343 (2)	C32—H32	0.9300
C12—N4	1.378 (2)	C33—O2	1.2277 (19)
C12—C13	1.384 (2)	C33—O1	1.302 (2)
C12—C17	1.388 (2)	C34—O5	1.215 (2)
C13—C14	1.369 (3)	C34—O6	1.2853 (19)
C13—H13	0.9300	C35—O3	1.2204 (18)
C14—C15	1.393 (3)	C35—O4	1.2893 (19)
C14—H14	0.9300	N1—H1A	0.8600
C15—C16	1.374 (2)	N2—H2A	0.8600
C15—H15	0.9300	N4—H4A	0.8600
C16—C17	1.384 (2)	O1—H1	0.8200
C16—H16	0.9300	O4—H4	0.8200
C17—N3	1.394 (2)	O6—H6	0.8200
C18—C19	1.387 (2)	O7—H7	0.8200
C18—C23	1.390 (2)	O9—H9	0.8200
C18—C24	1.497 (2)	O1W—H2	0.8561
C19—C20	1.394 (2)	O1W—H3	0.8490
C2—C1—C6	116.25 (18)	C20—C19—H19	120.0
C2—C1—H221	121.9	C21—C20—C19	119.67 (15)
C6—C1—H221	121.9	C21—C20—C25	117.19 (14)
C1—C2—C3	121.6 (2)	C19—C20—C25	123.13 (14)
C1—C2—H222	119.2	C22—C21—C20	121.04 (14)
C3—C2—H222	119.2	C22—C21—H21	119.5
C4—C3—C2	122.5 (2)	C20—C21—H21	119.5
C4—C3—H223	118.8	C23—C22—C21	118.60 (15)
C2—C3—H223	118.8	C23—C22—C26	121.43 (15)
C3—C4—C5	115.98 (18)	C21—C22—C26	119.98 (14)
C3—C4—H224	122.0	C22—C23—C18	121.36 (15)
C5—C4—H224	122.0	C22—C23—H23	119.3
C4—C5—N2	132.23 (17)	C18—C23—H23	119.3
C4—C5—C6	121.61 (18)	O8—C24—O7	124.20 (15)
N2—C5—C6	106.13 (15)	O8—C24—C18	124.19 (16)
C1—C6—N1	131.79 (16)	O7—C24—C18	111.60 (14)
C1—C6—C5	122.11 (17)	O10—C25—O9	122.68 (15)
N1—C6—C5	106.09 (15)	O10—C25—C20	121.29 (15)
N1—C7—N2	108.36 (16)	O9—C25—C20	116.02 (14)
N1—C7—C8	124.59 (16)	O11—C26—O12	123.93 (15)
N2—C7—C8	126.98 (17)	O11—C26—C22	118.80 (15)
C7—C8—C9	113.30 (16)	O12—C26—C22	117.27 (14)
C7—C8—H8A	108.9	C32—C27—C28	119.36 (15)
C9—C8—H8A	108.9	C32—C27—C33	117.75 (14)
C7—C8—H8B	108.9	C28—C27—C33	122.88 (15)
C9—C8—H8B	108.9	C29—C28—C27	120.05 (15)
H8A—C8—H8B	107.7	C29—C28—H28	120.0
C8—C9—C10	115.43 (15)	C27—C28—H28	120.0
C8—C9—H9A	108.4	C30—C29—C28	119.73 (14)
C10—C9—H9A	108.4	C30—C29—C34	118.75 (15)
C8—C9—H9B	108.4	C28—C29—C34	121.51 (15)
C10—C9—H9B	108.4	C29—C30—C31	120.69 (15)
H9A—C9—H9B	107.5	C29—C30—H30	119.7
C11—C10—C9	114.59 (14)	C31—C30—H30	119.7
C11—C10—H10A	108.6	C32—C31—C30	118.75 (14)
C9—C10—H10A	108.6	C32—C31—C35	118.50 (13)
C11—C10—H10B	108.6	C30—C31—C35	122.74 (14)
C9—C10—H10B	108.6	C27—C32—C31	121.41 (14)
H10A—C10—H10B	107.6	C27—C32—H32	119.3
N3—C11—N4	110.65 (15)	C31—C32—H32	119.3
N3—C11—C10	126.11 (16)	O2—C33—O1	123.21 (16)
N4—C11—C10	123.23 (15)	O2—C33—C27	121.45 (15)
N4—C12—C13	132.57 (16)	O1—C33—C27	115.34 (14)
N4—C12—C17	105.30 (15)	O5—C34—O6	124.88 (15)
C13—C12—C17	122.10 (17)	O5—C34—C29	120.36 (15)
C14—C13—C12	116.70 (17)	O6—C34—C29	114.75 (15)
C14—C13—H13	121.6	O3—C35—O4	124.28 (15)
C12—C13—H13	121.6	O3—C35—C31	120.99 (15)
C13—C14—C15	121.71 (19)	O4—C35—C31	114.73 (14)
C13—C14—H14	119.1	C7—N1—C6	109.82 (14)
C15—C14—H14	119.1	C7—N1—H1A	125.1
C16—C15—C14	121.43 (19)	C6—N1—H1A	125.1
C16—C15—H15	119.3	C7—N2—C5	109.58 (15)
C14—C15—H15	119.3	C7—N2—H2A	125.2
C15—C16—C17	117.37 (16)	C5—N2—H2A	125.2
C15—C16—H16	121.3	C11—N3—C17	106.47 (13)
C17—C16—H16	121.3	C11—N4—C12	108.91 (13)
C16—C17—C12	120.65 (15)	C11—N4—H4A	125.5
C16—C17—N3	130.69 (14)	C12—N4—H4A	125.5
C12—C17—N3	108.65 (14)	C33—O1—H1	109.5
C19—C18—C23	119.38 (14)	C35—O4—H4	109.5
C19—C18—C24	120.47 (14)	C34—O6—H6	109.5
C23—C18—C24	120.14 (15)	C24—O7—H7	109.5
C18—C19—C20	119.91 (15)	C25—O9—H9	109.5
C18—C19—H19	120.0	H2—O1W—H3	105.4
C6—C1—C2—C3	−0.1 (3)	C21—C20—C25—O9	−177.31 (16)
C1—C2—C3—C4	0.7 (4)	C19—C20—C25—O9	3.7 (3)
C2—C3—C4—C5	−0.3 (3)	C23—C22—C26—O11	−176.01 (16)
C3—C4—C5—N2	−178.11 (19)	C21—C22—C26—O11	4.1 (2)
C3—C4—C5—C6	−0.5 (3)	C23—C22—C26—O12	3.1 (2)
C2—C1—C6—N1	178.2 (2)	C21—C22—C26—O12	−176.72 (17)
C2—C1—C6—C5	−0.7 (3)	C32—C27—C28—C29	−0.6 (3)
C4—C5—C6—C1	1.1 (3)	C33—C27—C28—C29	178.26 (17)
N2—C5—C6—C1	179.23 (16)	C27—C28—C29—C30	0.8 (3)
C4—C5—C6—N1	−178.06 (17)	C27—C28—C29—C34	−178.12 (15)
N2—C5—C6—N1	0.1 (2)	C28—C29—C30—C31	−0.7 (2)
N1—C7—C8—C9	−104.6 (2)	C34—C29—C30—C31	178.24 (15)
N2—C7—C8—C9	72.0 (2)	C29—C30—C31—C32	0.4 (2)
C7—C8—C9—C10	72.0 (2)	C29—C30—C31—C35	−178.30 (15)
C8—C9—C10—C11	−64.1 (2)	C28—C27—C32—C31	0.3 (3)
C9—C10—C11—N3	−48.0 (3)	C33—C27—C32—C31	−178.63 (16)
C9—C10—C11—N4	131.08 (18)	C30—C31—C32—C27	−0.2 (3)
N4—C12—C13—C14	−178.6 (2)	C35—C31—C32—C27	178.58 (15)
C17—C12—C13—C14	−1.0 (3)	C32—C27—C33—O2	4.6 (3)
C12—C13—C14—C15	−0.7 (3)	C28—C27—C33—O2	−174.27 (18)
C13—C14—C15—C16	1.8 (3)	C32—C27—C33—O1	−175.43 (17)
C14—C15—C16—C17	−1.0 (3)	C28—C27—C33—O1	5.7 (3)
C15—C16—C17—C12	−0.6 (3)	C30—C29—C34—O5	1.0 (3)
C15—C16—C17—N3	178.61 (17)	C28—C29—C34—O5	179.92 (18)
N4—C12—C17—C16	179.87 (16)	C30—C29—C34—O6	−178.12 (15)
C13—C12—C17—C16	1.7 (3)	C28—C29—C34—O6	0.8 (2)
N4—C12—C17—N3	0.49 (18)	C32—C31—C35—O3	6.9 (2)
C13—C12—C17—N3	−177.72 (16)	C30—C31—C35—O3	−174.34 (16)
C23—C18—C19—C20	1.2 (2)	C32—C31—C35—O4	−173.69 (16)
C24—C18—C19—C20	−177.37 (15)	C30—C31—C35—O4	5.0 (2)
C18—C19—C20—C21	−2.2 (3)	N2—C7—N1—C6	−1.6 (2)
C18—C19—C20—C25	176.72 (17)	C8—C7—N1—C6	175.51 (17)
C19—C20—C21—C22	1.4 (3)	C1—C6—N1—C7	−178.09 (19)
C25—C20—C21—C22	−177.55 (17)	C5—C6—N1—C7	0.9 (2)
C20—C21—C22—C23	0.3 (3)	N1—C7—N2—C5	1.7 (2)
C20—C21—C22—C26	−179.84 (15)	C8—C7—N2—C5	−175.36 (17)
C21—C22—C23—C18	−1.3 (2)	C4—C5—N2—C7	176.8 (2)
C26—C22—C23—C18	178.84 (15)	C6—C5—N2—C7	−1.1 (2)
C19—C18—C23—C22	0.5 (2)	N4—C11—N3—C17	−1.25 (19)
C24—C18—C23—C22	179.15 (15)	C10—C11—N3—C17	177.92 (16)
C19—C18—C24—O8	−11.2 (3)	C16—C17—N3—C11	−178.86 (18)
C23—C18—C24—O8	170.21 (16)	C12—C17—N3—C11	0.44 (18)
C19—C18—C24—O7	167.73 (15)	N3—C11—N4—C12	1.6 (2)
C23—C18—C24—O7	−10.9 (2)	C10—C11—N4—C12	−177.60 (16)
C21—C20—C25—O10	3.5 (3)	C13—C12—N4—C11	176.7 (2)
C19—C20—C25—O10	−175.51 (18)	C17—C12—N4—C11	−1.24 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O10i	0.82	1.82	2.6404 (16)	178
O9—H9···O2i	0.82	1.85	2.6682 (16)	177
N1—H1A···O11	0.86	1.84	2.6560 (17)	159
N4—H4A···O3	0.86	2.05	2.8435 (17)	153
C1—H221···O10	0.93	2.51	3.414 (2)	163
C9—H9A···O5ii	0.97	2.44	3.346 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O10i	0.82	1.82	2.6404 (16)	178
O9—H9⋯O2i	0.82	1.85	2.6682 (16)	177
N1—H1A⋯O11	0.86	1.84	2.6560 (17)	159
N4—H4A⋯O3	0.86	2.05	2.8435 (17)	153
C1—H221⋯O10	0.93	2.51	3.414 (2)	163
C9—H9A⋯O5ii	0.97	2.44	3.346 (2)	156

Symmetry codes: (i) ; (ii) .