trans-1,2-Bis(1-methyl­benzimidazol-2-yl)cyclo­hexane monohydrate

Chiral mol­ecules of the title compound, C₂₂H₂₄N₄·H₂O, have approximate twofold symmetry, essentially planar benzimid­azole fragments, and a ladder-like appearance in profile, with the benzimidazole planes exhibiting a dihedral angle of 68.75 (4)°. Geometric parameters are consistent with those of comparable species containing benzimidazole or cyclo­hexyl fragments. Adventitious water mol­ecules of solvation form strong O—H...N(imine) hydrogen bonds to yield infinite 2₁ columns along the c-axis direction. The columns are related by glide-plane symmetry operations and are linked by C—H...π inter­actions to yield racemic crystals.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.106
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.831     1.000
            Tmin(prime) and Tmax expected:      0.977     0.998
            RR(prime) =      0.849
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.55
           From the CIF: _reflns_number_total               3030
           Count of symmetry unique reflns         3029
           Completeness (_total/calc)            100.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Bis(2-benzimidazol-2-yl)species, (I), bridged by a variety of alkyl or aryl spacers, X, are remarkably versatile. They have, for example, been tested as anti-tumoor and antimicrobial agents (Baraldi et al., 2004), and as topoisomerase inhibitors (Walker & Saravia, 2004). Furthermore, they have been used as polymerization catalysts (Stibrany, 2001), as agents to study electron self-exchange (Knapp et al., 1990; Xie et al., 1999), in selective ion-exchange resins (van Berkel et al., 1995), as proton sponges (Stibrany et al., 2002), and as geometrically constraining ligands (Stibrany et al., 2004). Here, we report the structure of the title compound, (II), a bis(benzimidazole) ligand with a rigid two-carbon bridge and two torsional degrees of freedom.

Molecules of (II) (Fig. 1) exhibit approximate diad axes, which pass through the midpoints of the C31—C32 and C34—C35 bonds of the cyclohexyl fragments. Both benzimidazole fragments are essentially planar, as expected, and they are oriented in such a way as to give the molecule a ladder-like appearance in profile (Fig. 2). The dihedral angle between the benzimidazole planes [68.75 (4)°] is approximately 5° larger than that reported for bis(benzimidazole-2-yl)methane [63.53 (2)°; Duan et al., 2005], a molecule related to (II) but with R = H and with a one-carbon atom bridge X = CH₂. Geometric parameters for (II) (Table 1) agree well with those reported for other structures of bis(benzimidazole)s with rigid two-carbon bridges (Stibrany et al., 2005). In particular, in the N—C—N fragments, the C—N(imine) distances are approximately 0.05 Å shorter than the C—N(amine) distances, consonant with the partial double-bond character of the former bonds.

In the crystal structure of (II), water molecules of solvation form strong O—H···N(imine) hydrogen bonds (Table 2) with the organic molecules to yield infinite chains or columns parallel to the c axis direction, in which successive molecules of a given type are related by the 2₁ symmetry operations of the space group (Fig. 3). The organic molecules of (II) are chiral and, as a result, individual `2₁' columns contain one enantiomer exclusively. The glide-plane symmetry operations produce parallel columns containing the other enantiomer exclusively and, as a result, crystals of (II) are racemic. To complete the structure, the columns are linked by C—H···π interactions, some of which are shown in Table 3. There is little, if any, evidence for π–π stacking.

S2. Experimental

Trans-1,2-bis(1-methylbenzimidazol-2-yl)cyclohexane hydrate was prepared in two steps. Firstly, trans(1,2-bis(1-H-benzimidazol-2-yl) was prepared by the Phillips condensation method (Phillips, 1931) from trans-1,2-cyclohexane dicarboxylic acid and two equivalents of 1,2-phenylenediamine. Secondly, using the procedure described previously by Stibrany et al. (2004), methylation of the amine N atoms, effected using methyl iodide, yielded the non-hydrated product. Crystals of the title compound, (II), were obtained by slow evaporation in air of an acetone solution of the product. Incorporation of adventitious water resulted in the monohydrate [m.p. 479 K (soften), 491 K (melt)]. Spectroscopic analysis: IR (KBr pellet, cm⁻¹): 3384 (m), 3051 (w), 2929 (s), 2853 (m), 1614 (w), 1468 (s), 1443 (s), 1329 (m), 1008 (w), 745 (s).

S3. Refinement

The water H atoms, which are involved in hydrogen bonding, were refined isotropically. C-bound H atoms were positioned geometrically and treated as riding, with Csp²—H and Csp³—H distances set to 0.93 and 0.96 Å, respectively, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(C), respectively. A final difference Fourier map revealed 37 peaks larger than the absolute value of the largest negative peak. Of these, 33 of the first 35 peaks were located approximately midway along the C—C or C—N vectors, of which there are a total of 30 in the molecular framework. The 33 peaks are consistent with residual bond density, with three of the bonds exhibiting split peaks.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. The structure of the cation [? No charge. `Organic molecule' better?] of (II), showing 25% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. A view of the organic molecule of (II), showing the benzimidazole planes in profile.
	Fig. 3. A projection, along the a axis, of the structure of (II). O atoms are coloured pink [Purple?] and hydrogen bonds are indicated by dashed lines.

trans-1,2-Bis(1-methylbenzimidazol-2-yl)cyclohexane monohydrate

Crystal data

C22H24N4·H2O	Dx = 1.264 Mg m^−3
Mr = 362.47	Melting point: 479 K (soften), 491 K (melt) K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6763 reflections
a = 9.6596 (7) Å	θ = 2.5–30.6°
b = 14.5552 (11) Å	µ = 0.08 mm^−1
c = 13.547 (1) Å	T = 100 K
V = 1904.7 (2) Å^3	Lath, colourless
Z = 4	0.29 × 0.14 × 0.03 mm
F(000) = 776

Data collection

Bruker SMART CCD area-detector diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ϕ and ω scans	θmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −12→13
Tmin = 0.831, Tmax = 1.00	k = −10→20
14429 measured reflections	l = −19→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.2238P] where P = (Fo^2 + 2Fc^2)/3
3030 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.37 e Å^−3
1 restraint	Δρmin = −0.16 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.81216 (16)	1.00399 (11)	0.92421 (12)	0.0190 (3)
N13	0.64846 (16)	0.93479 (11)	1.01498 (13)	0.0183 (3)
N21	0.41947 (15)	0.81453 (10)	0.82663 (12)	0.0163 (3)
N23	0.58166 (16)	0.89532 (11)	0.74536 (12)	0.0179 (3)
C11	0.88160 (19)	0.94786 (12)	0.99015 (14)	0.0192 (3)
C12	0.67326 (17)	0.99353 (12)	0.94277 (14)	0.0176 (3)
C13	0.77785 (18)	0.90483 (13)	1.04589 (14)	0.0182 (3)
C14	0.8138 (2)	0.84054 (14)	1.11798 (14)	0.0217 (4)
H14	0.7462	0.8109	1.1550	0.026*
C15	0.9528 (2)	0.82222 (16)	1.13281 (17)	0.0268 (4)
H15	0.9785	0.7787	1.1797	0.032*
C16	1.0559 (2)	0.86786 (15)	1.07863 (17)	0.0272 (4)
H16	1.1486	0.8557	1.0920	0.033*
C17	1.02215 (19)	0.93073 (14)	1.00551 (17)	0.0244 (4)
H17	1.0900	0.9601	0.9684	0.029*
C18	0.8761 (2)	1.06134 (14)	0.84882 (19)	0.0301 (5)
H18A	0.8291	1.0525	0.7871	0.045*
H18B	0.9717	1.0447	0.8417	0.045*
H18C	0.8695	1.1247	0.8679	0.045*
C21	0.48462 (18)	0.75291 (12)	0.76407 (13)	0.0165 (3)
C22	0.48202 (17)	0.89762 (12)	0.81235 (13)	0.0158 (3)
C23	0.58566 (18)	0.80432 (12)	0.71422 (14)	0.0169 (3)
C24	0.67272 (19)	0.76034 (13)	0.64641 (13)	0.0200 (4)
H24	0.7401	0.7930	0.6122	0.024*
C25	0.6559 (2)	0.66706 (13)	0.63174 (16)	0.0222 (4)
H25	0.7143	0.6367	0.5880	0.027*
C26	0.5529 (2)	0.61712 (13)	0.68122 (15)	0.0214 (4)
H26	0.5434	0.5546	0.6688	0.026*
C27	0.46464 (19)	0.65946 (12)	0.74862 (14)	0.0194 (3)
H27	0.3959	0.6269	0.7816	0.023*
C28	0.3083 (2)	0.79329 (13)	0.89543 (15)	0.0213 (4)
H28A	0.3353	0.8111	0.9609	0.032*
H28B	0.2898	0.7285	0.8941	0.032*
H28C	0.2263	0.8263	0.8767	0.032*
C31	0.56325 (19)	1.04464 (12)	0.88790 (14)	0.0173 (3)
H31	0.6009	1.0642	0.8241	0.021*
C32	0.43844 (18)	0.98159 (12)	0.86918 (13)	0.0161 (3)
H32	0.4028	0.9614	0.9333	0.019*
C33	0.32200 (19)	1.03345 (12)	0.81575 (15)	0.0193 (3)
H33A	0.3537	1.0524	0.7509	0.023*
H33B	0.2431	0.9931	0.8071	0.023*
C34	0.2784 (2)	1.11799 (13)	0.87522 (16)	0.0227 (4)
H34A	0.2073	1.1512	0.8394	0.027*
H34B	0.2397	1.0986	0.9379	0.027*
C35	0.4018 (2)	1.18153 (13)	0.89374 (15)	0.0231 (4)
H35A	0.4353	1.2053	0.8313	0.028*
H35B	0.3724	1.2332	0.9338	0.028*
C36	0.5189 (2)	1.13053 (13)	0.94622 (15)	0.0215 (4)
H36A	0.4884	1.1124	1.0116	0.026*
H36B	0.5976	1.1713	0.9537	0.026*
O1	0.38699 (16)	0.93244 (12)	0.12819 (13)	0.0280 (3)
H1O	0.464 (3)	0.927 (2)	0.099 (2)	0.030 (7)*
H2O	0.386 (3)	0.984 (2)	0.158 (3)	0.046 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0208 (7)	0.0175 (7)	0.0188 (8)	−0.0020 (5)	0.0032 (6)	−0.0036 (6)
N13	0.0198 (7)	0.0214 (7)	0.0137 (7)	−0.0001 (5)	−0.0005 (5)	0.0003 (6)
N21	0.0194 (6)	0.0153 (7)	0.0142 (7)	0.0012 (5)	0.0004 (5)	0.0003 (6)
N23	0.0206 (6)	0.0175 (7)	0.0157 (7)	−0.0003 (5)	−0.0001 (6)	0.0001 (6)
C11	0.0206 (8)	0.0184 (8)	0.0185 (8)	−0.0004 (6)	0.0013 (6)	−0.0065 (7)
C12	0.0192 (8)	0.0173 (8)	0.0163 (9)	−0.0011 (6)	0.0014 (6)	−0.0041 (7)
C13	0.0190 (7)	0.0212 (8)	0.0144 (8)	0.0008 (6)	−0.0004 (6)	−0.0033 (6)
C14	0.0229 (8)	0.0271 (9)	0.0151 (9)	0.0039 (7)	0.0001 (7)	−0.0015 (7)
C15	0.0284 (9)	0.0332 (11)	0.0188 (9)	0.0090 (8)	−0.0033 (8)	−0.0027 (8)
C16	0.0205 (8)	0.0339 (10)	0.0272 (10)	0.0069 (8)	−0.0023 (7)	−0.0094 (9)
C17	0.0194 (8)	0.0266 (9)	0.0272 (10)	−0.0005 (7)	0.0029 (7)	−0.0068 (8)
C18	0.0337 (10)	0.0210 (9)	0.0355 (12)	−0.0024 (8)	0.0151 (9)	0.0030 (8)
C21	0.0188 (7)	0.0173 (7)	0.0134 (7)	0.0022 (6)	−0.0009 (6)	0.0003 (6)
C22	0.0181 (7)	0.0158 (7)	0.0135 (8)	0.0007 (6)	−0.0021 (6)	0.0012 (6)
C23	0.0198 (7)	0.0165 (8)	0.0143 (8)	0.0012 (6)	−0.0026 (6)	−0.0003 (6)
C24	0.0218 (8)	0.0237 (8)	0.0145 (8)	0.0011 (6)	0.0012 (6)	0.0001 (7)
C25	0.0277 (9)	0.0222 (8)	0.0168 (8)	0.0056 (7)	0.0019 (7)	−0.0031 (7)
C26	0.0291 (9)	0.0153 (8)	0.0198 (9)	0.0031 (7)	−0.0015 (7)	−0.0021 (7)
C27	0.0235 (8)	0.0164 (8)	0.0184 (9)	−0.0001 (6)	0.0001 (6)	−0.0003 (7)
C28	0.0251 (8)	0.0187 (8)	0.0201 (9)	−0.0029 (6)	0.0051 (7)	−0.0006 (7)
C31	0.0223 (8)	0.0141 (7)	0.0155 (8)	−0.0006 (6)	−0.0004 (6)	0.0005 (6)
C32	0.0208 (7)	0.0142 (7)	0.0133 (8)	0.0008 (6)	−0.0012 (6)	−0.0002 (6)
C33	0.0226 (8)	0.0187 (8)	0.0167 (8)	0.0036 (6)	−0.0028 (7)	−0.0005 (7)
C34	0.0277 (9)	0.0217 (8)	0.0187 (9)	0.0070 (7)	0.0015 (7)	0.0014 (7)
C35	0.0340 (10)	0.0171 (8)	0.0182 (9)	0.0027 (7)	0.0018 (7)	0.0013 (7)
C36	0.0306 (9)	0.0148 (7)	0.0192 (9)	0.0007 (7)	−0.0001 (7)	−0.0017 (7)
O1	0.0273 (7)	0.0333 (8)	0.0233 (7)	−0.0082 (6)	0.0041 (6)	−0.0066 (7)

Geometric parameters (Å, º)

N11—C12	1.374 (2)	C23—C24	1.400 (3)
N21—C22	1.366 (2)	C24—C25	1.382 (3)
N13—C12	1.321 (3)	C24—H24	0.9300
N23—C22	1.323 (2)	C25—C26	1.403 (3)
N11—C11	1.384 (3)	C25—H25	0.9300
N21—C21	1.385 (2)	C26—C27	1.393 (3)
N13—C13	1.388 (2)	C26—H26	0.9300
N23—C23	1.391 (2)	C27—H27	0.9300
C11—C13	1.402 (3)	C28—H28A	0.9600
C21—C23	1.403 (3)	C28—H28B	0.9600
C12—C31	1.495 (2)	C28—H28C	0.9600
C22—C32	1.505 (2)	C31—C36	1.540 (3)
C31—C32	1.536 (2)	C31—H31	0.9800
N11—C18	1.456 (3)	C32—C33	1.536 (2)
N21—C28	1.455 (2)	C32—H32	0.9800
C11—C17	1.396 (3)	C33—C34	1.530 (3)
C13—C14	1.396 (3)	C33—H33A	0.9700
C14—C15	1.384 (3)	C33—H33B	0.9700
C14—H14	0.9300	C34—C35	1.529 (3)
C15—C16	1.404 (3)	C34—H34A	0.9700
C15—H15	0.9300	C34—H34B	0.9700
C16—C17	1.387 (3)	C35—C36	1.528 (3)
C16—H16	0.9300	C35—H35A	0.9700
C17—H17	0.9300	C35—H35B	0.9700
C18—H18A	0.9600	C36—H36A	0.9700
C18—H18B	0.9600	C36—H36B	0.9700
C18—H18C	0.9600	O1—H1O	0.85 (3)
C21—C27	1.390 (3)	O1—H2O	0.85 (3)
N13—C12—N11	112.60 (16)	C27—C26—C25	121.20 (18)
N23—C22—N21	113.36 (16)	C27—C26—H26	119.4
C12—N11—C11	106.85 (15)	C25—C26—H26	119.4
C22—N21—C21	106.60 (15)	C21—C27—C26	116.54 (18)
C12—N13—C13	105.27 (15)	C21—C27—H27	121.7
C22—N23—C23	104.61 (15)	C26—C27—H27	121.7
N11—C11—C13	105.36 (16)	N21—C28—H28A	109.5
N21—C21—C23	105.38 (15)	N21—C28—H28B	109.5
N13—C13—C11	109.91 (16)	H28A—C28—H28B	109.5
N23—C23—C21	110.04 (16)	N21—C28—H28C	109.5
C12—N11—C18	127.30 (17)	H28A—C28—H28C	109.5
C11—N11—C18	125.84 (17)	H28B—C28—H28C	109.5
C22—N21—C28	127.25 (15)	C12—C31—C32	110.03 (14)
C21—N21—C28	126.14 (15)	C12—C31—C36	110.29 (15)
N11—C11—C17	132.30 (18)	C32—C31—C36	110.57 (15)
C17—C11—C13	122.34 (19)	C12—C31—H31	108.6
N13—C12—C31	124.15 (15)	C32—C31—H31	108.6
N11—C12—C31	123.24 (16)	C36—C31—H31	108.6
N13—C13—C14	130.19 (17)	C22—C32—C33	111.28 (15)
C14—C13—C11	119.87 (17)	C22—C32—C31	110.50 (14)
C15—C14—C13	118.17 (19)	C33—C32—C31	111.04 (15)
C15—C14—H14	120.9	C22—C32—H32	108.0
C13—C14—H14	120.9	C33—C32—H32	108.0
C14—C15—C16	121.4 (2)	C31—C32—H32	108.0
C14—C15—H15	119.3	C34—C33—C32	110.40 (16)
C16—C15—H15	119.3	C34—C33—H33A	109.6
C17—C16—C15	121.22 (18)	C32—C33—H33A	109.6
C17—C16—H16	119.4	C34—C33—H33B	109.6
C15—C16—H16	119.4	C32—C33—H33B	109.6
C16—C17—C11	116.93 (19)	H33A—C33—H33B	108.1
C16—C17—H17	121.5	C35—C34—C33	111.00 (16)
C11—C17—H17	121.5	C35—C34—H34A	109.4
N11—C18—H18A	109.5	C33—C34—H34A	109.4
N11—C18—H18B	109.5	C35—C34—H34B	109.4
H18A—C18—H18B	109.5	C33—C34—H34B	109.4
N11—C18—H18C	109.5	H34A—C34—H34B	108.0
H18A—C18—H18C	109.5	C36—C35—C34	111.06 (16)
H18B—C18—H18C	109.5	C36—C35—H35A	109.4
N21—C21—C27	131.51 (17)	C34—C35—H35A	109.4
C27—C21—C23	123.10 (17)	C36—C35—H35B	109.4
N23—C22—C32	125.09 (16)	C34—C35—H35B	109.4
N21—C22—C32	121.54 (16)	H35A—C35—H35B	108.0
N23—C23—C24	130.62 (17)	C35—C36—C31	111.20 (16)
C24—C23—C21	119.32 (16)	C35—C36—H36A	109.4
C25—C24—C23	118.23 (17)	C31—C36—H36A	109.4
C25—C24—H24	120.9	C35—C36—H36B	109.4
C23—C24—H24	120.9	C31—C36—H36B	109.4
C24—C25—C26	121.59 (18)	H36A—C36—H36B	108.0
C24—C25—H25	119.2	H1O—O1—H2O	108 (3)
C26—C25—H25	119.2
C12—N11—C11—C17	−179.9 (2)	C22—N23—C23—C24	−177.98 (19)
C18—N11—C11—C17	1.1 (3)	C22—N23—C23—C21	0.53 (19)
C12—N11—C11—C13	0.49 (19)	N21—C21—C23—N23	−0.3 (2)
C18—N11—C11—C13	−178.46 (18)	C27—C21—C23—N23	−179.62 (17)
C13—N13—C12—N11	0.0 (2)	N21—C21—C23—C24	178.41 (15)
C13—N13—C12—C31	−178.96 (16)	C27—C21—C23—C24	−0.9 (3)
C11—N11—C12—N13	−0.3 (2)	N23—C23—C24—C25	177.99 (19)
C18—N11—C12—N13	178.58 (18)	C21—C23—C24—C25	−0.4 (3)
C11—N11—C12—C31	178.67 (16)	C23—C24—C25—C26	1.4 (3)
C18—N11—C12—C31	−2.4 (3)	C24—C25—C26—C27	−1.1 (3)
C12—N13—C13—C14	−177.9 (2)	N21—C21—C27—C26	−177.93 (18)
C12—N13—C13—C11	0.3 (2)	C23—C21—C27—C26	1.2 (3)
N11—C11—C13—N13	−0.49 (19)	C25—C26—C27—C21	−0.2 (3)
C17—C11—C13—N13	179.87 (17)	N13—C12—C31—C32	−39.6 (2)
N11—C11—C13—C14	177.93 (17)	N11—C12—C31—C32	141.48 (17)
C17—C11—C13—C14	−1.7 (3)	N13—C12—C31—C36	82.6 (2)
N13—C13—C14—C15	178.84 (19)	N11—C12—C31—C36	−96.3 (2)
C11—C13—C14—C15	0.8 (3)	N23—C22—C32—C33	91.0 (2)
C13—C14—C15—C16	1.2 (3)	N21—C22—C32—C33	−89.1 (2)
C14—C15—C16—C17	−2.4 (3)	N23—C22—C32—C31	−32.9 (2)
C15—C16—C17—C11	1.5 (3)	N21—C22—C32—C31	147.01 (16)
N11—C11—C17—C16	−178.97 (19)	C12—C31—C32—C22	−57.82 (19)
C13—C11—C17—C16	0.6 (3)	C36—C31—C32—C22	−179.89 (15)
C22—N21—C21—C27	179.19 (19)	C12—C31—C32—C33	178.20 (16)
C28—N21—C21—C27	0.5 (3)	C36—C31—C32—C33	56.12 (19)
C22—N21—C21—C23	−0.05 (19)	C22—C32—C33—C34	179.48 (15)
C28—N21—C21—C23	−178.78 (16)	C31—C32—C33—C34	−57.0 (2)
C23—N23—C22—N21	−0.6 (2)	C32—C33—C34—C35	57.1 (2)
C23—N23—C22—C32	179.29 (16)	C33—C34—C35—C36	−56.7 (2)
C21—N21—C22—N23	0.4 (2)	C34—C35—C36—C31	55.9 (2)
C28—N21—C22—N23	179.12 (16)	C12—C31—C36—C35	−177.43 (15)
C21—N21—C22—C32	−179.47 (15)	C32—C31—C36—C35	−55.5 (2)
C28—N21—C22—C32	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N13^i	0.85 (3)	2.12 (3)	2.955 (2)	171 (2)
O1—H2O···N23^ii	0.85 (3)	2.14 (3)	2.983 (2)	170 (2)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, z−1/2.