6,6'-Di­methoxy-2,2'-[(1R,2R)-cyclo­hexane-1,2-diyl­bis­(nitrilo­methyl­idyne)]­diphenol: three C-H...O hydrogen bonds generate a three-dimensional framework

Molecules of the title compound, alternatively called (R,R)-N,N'-bis(3-methoxysalicylidene)-trans-cyclohexane-1,2-diamine, C₂₂H₂₆N₂O₄, contain two intramolecular O-H...N hydrogen bonds and adopt a conformation with approximate twofold rotational symmetry. The mol­ecules are linked by three C-H...O hydrogen bonds [H...O = 2.45-2.55 Å, C...O = 3.329 (2)-3.398 (2) Å and C-H...O = 142-172°] into a continuous framework.

S1. Comment

Chiral Schiff base complexes have been used as efficient catalysts for Michael reactions (Jha & Joshi, 2001), for epoxidation (Larrow & Jacobson, 1994) and for aziridination (Liang et al., 2002) of alkenes. Furthermore the N atoms of azomethine groups in metal complexes can act as hydrogen-bond acceptors, and it has been proposed that this interaction can account for some of the antibacterial and antifungal activities of ruthenium complexes (Ramesh & Sivagamasundari, 2003). The title compound, (I), was prepared as a forerunner to the synthesis and investigation of chiral ruthenium Schiff base complexes, and the present structural investigation was undertaken in order to assign unambiguously the structure and the hydrogen bonding.

The cyclohexane moiety adopts the usual chain conformation, with the two substituents in equatorial sites. There are two intramolecular O—H···N hydrogen bonds (Fig. 1), each forming an S(6) motif (Bernstein et al., 1995), and these undoubtedly play a part in controlling the overall molecular conformation. This conformation is close to C₂ symmetry, but examination of the key torsion angles (Table 1) confirms the absence of exact twofold rotational symmetry. The bond distances show no unusual features, and the exocyclic C—C—O angles at C13 and C23 show the usual pattern (Seip & Seip, 1973; Ferguson et al., 1996; Patterson et al., 1998; Abonia et al., 2003)

The absence of twofold rotational symmetry is confirmed by the pattern and dimensions of the soft (Desiraju & Steiner, 1999) C—H···O hydrogen bonds (Table 2), where one phenyl ring, C11–C16, provides only one donor and one acceptor, while the other ring, C21–C26, provides two donors and two acceptors. These three hydrogen bonds serve to link the molecules into a continuous three-dimensional framework, whose description can be simplified by the use of the substructure approach (Gregson et al., 2000).

Atom C14 in the molecule at (x, y, z) acts as a hydrogen-bond donor to phenol atom O22 in the molecule at (−0.5 + x, −0.5 − y, 1 − z), while atom C14 at (−0.5 + x, −0.5 − y, 1 − z) in turn acts as a donor to atom O22 at (−1 + x, y, z), so producing a C(14) chain running parallel to the [100] direction and generated by the 2₁ screw axis along (x, −0.25, 1/2). At the same time, atom C24 at (x, y, z) acts as a donor to methoxyl atom O23 at (−0.5 + x, 0.5 − y, 1 − z), so producing a C(4) chain around the 2₁ screw axis along (x, 1/4, 1/2). These two chain motifs combine to produce a (001) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R⁴₄(38) ring (Fig. 2). Two sheets of this type pass through each unit cell, in the domains 0.23 < z < 0.77 and 0.73 < z < 1.27, and these sheets are linked into a single framework by the third of the C—H···O hydrogen bonds.

Atom C26 in the molecule at (x, y, z) acts as a hydrogen bond donor to phenol atom O12 in the molecule at (1 − x, 0.5 + y, 1.5 − z), and propagation of this interaction produces a C(12) chain running parallel to the [010] direction and generated by the 2₁ screw axis along (1/2, y, 3/4) (Fig. 3). The molecules at (x, y, z) and (1 − x, 0.5 + y, 1.5 − z) lie, respectively, in the 0.23 < z < 0.77 and 0.73 < z < 1.27 sheets. Similarly, atom C26 in the molecule at (−0.5 + x, −0.5 − y, 1 − z), which also lies in the 0.23 < z < 0.77 sheet, acts as a hydrogen-bond donor to atom O12 in the molecule at (0.5 − x, −1 − y, −0.5 + z), which lies in the −0.27 < z < 0.27 sheet. Hence, this hydrogen bond links each (001) sheet to the two neighbouring sheets, so forming a single continuous framework.

S2. Experimental

The Schiff base was obtained by refluxing a mixture of 2-methoxysalicylaldehyde (20 mmol) and the L-(+)-tartaric acid salt of trans-(1R,2R)-1,2-diaminocyclohexane (10 mmol) in the presence of anhydrous potassium carbonate, with a methanol–water mixture as solvent. The crude product was obtained by removing the solvent at reduced pressure and was recrystallized from hexane (yield 85%; m.p. 401–403 K). Analysis found: C 69.1, H 6.4, N 7.2%; C₂₂H₂₆N₂O₄ requires: C 69.3, H 6.9, N 7.3%. IR (cm⁻¹): 3416 (OH), 1626 (C═N); NMR (CDCl₃): δ(H) 1.42–1.60 (m, 4H, CH₂), 1.86–1.96 (m, 4H, CH₂), 3.59 (m, 2H, CH), 3.93 (s, 6H, OCH₃), 6.3–7.2 (m, 6H, aromatic), 8.24 (s, 2H, CH═N), 13.81 (s, 2H, OH); [α]²³_D(CH₃OH), −46.9° dm⁻¹ g⁻¹ cm³.

S3. Refinement

Crystals of (I) are orthorhombic and the space group P2₁2₁2₁ was uniquely assigned from the systematic absences. All H atoms were treated as riding atoms, with C—H distances of 0.95 (aromatic), 0.98 (CH₃), 0.99 (CH₂) or 1.00 Å (aliphatic CH), and O—H distances of 0.84 Å. In the absence of significant anomalous scattering, the Flack (1983) parameter was indeterminate (Flack & Bernardinelli, 2000); hence the Friedel equivalents were merged before the final refinements, and the absolute structure was set by reference to the known (R,R) configuration of the trans-1,2-diaminocyclohexane used in the synthesis.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids have been drawn at the 30% probability level.
	Fig. 2. Stereoview of part of the crystal structure of (I), showing the formation of a (001) sheet of R^44(38) rings.
	Fig. 3. Part of the crystal structure of (I), showing the formation of the C(12) chain that links the (001) sheets. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 − x, 0.5 + y, 1.5 − z) and (x, 1 + y, z), respectively.

6,6'-Dimethoxy-2,2'-[(1R,2R)-cyclohexane-1,2- diylbis(nitrilomethylidyne)]diphenol

Crystal data

C22H26N2O4	F(000) = 816
Mr = 382.45	Dx = 1.252 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2642 reflections
a = 7.5558 (2) Å	θ = 3.0–27.4°
b = 13.4054 (1) Å	µ = 0.09 mm^−1
c = 20.0304 (3) Å	T = 120 K
V = 2028.85 (6) Å^3	Plate, yellow
Z = 4	0.32 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2642 independent reflections
Radiation source: rotating anode	2484 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan DENZO–SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.962, Tmax = 0.994	k = −17→17
27432 measured reflections	l = −25→25

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.3696P] where P = (Fo^2 + 2Fc^2)/3
2646 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	1.0437 (2)	−0.11601 (12)	0.67182 (8)	0.0204 (3)
C2	0.9595 (2)	−0.02665 (12)	0.70712 (8)	0.0211 (3)
C3	1.1026 (3)	0.04886 (13)	0.72695 (9)	0.0253 (4)
C4	1.2443 (3)	0.00097 (14)	0.77096 (9)	0.0277 (4)
C5	1.3229 (3)	−0.09167 (14)	0.73779 (10)	0.0290 (4)
C6	1.1799 (3)	−0.16624 (13)	0.71701 (9)	0.0261 (4)
N11	0.9037 (2)	−0.18570 (10)	0.65255 (7)	0.0217 (3)
C11	0.7886 (2)	−0.30840 (12)	0.57741 (8)	0.0206 (3)
C12	0.6279 (2)	−0.31617 (12)	0.61182 (8)	0.0209 (3)
C13	0.5024 (2)	−0.38805 (13)	0.59244 (8)	0.0221 (4)
C14	0.5402 (3)	−0.45242 (13)	0.53992 (8)	0.0245 (4)
C15	0.7010 (3)	−0.44442 (14)	0.50561 (8)	0.0266 (4)
C16	0.8224 (2)	−0.37285 (14)	0.52317 (8)	0.0254 (4)
C17	0.9218 (2)	−0.23634 (13)	0.59878 (8)	0.0220 (3)
O12	0.58846 (18)	−0.25746 (9)	0.66455 (6)	0.0261 (3)
O13	0.35034 (18)	−0.38910 (10)	0.62948 (6)	0.0288 (3)
N21	0.8314 (2)	0.02041 (11)	0.66217 (7)	0.0216 (3)
C21	0.5822 (2)	0.12585 (12)	0.64316 (8)	0.0201 (3)
C22	0.5832 (2)	0.10812 (12)	0.57386 (8)	0.0197 (3)
C23	0.4641 (2)	0.15965 (13)	0.53252 (8)	0.0216 (3)
C24	0.3470 (2)	0.22763 (13)	0.55988 (9)	0.0246 (4)
C25	0.3461 (3)	0.24471 (13)	0.62885 (9)	0.0271 (4)
C26	0.4615 (2)	0.19452 (13)	0.66997 (8)	0.0242 (4)
C27	0.7084 (2)	0.07493 (12)	0.68632 (8)	0.0211 (3)
C131	0.2188 (3)	−0.46056 (15)	0.61131 (10)	0.0333 (4)
C231	0.3662 (3)	0.19237 (15)	0.42151 (9)	0.0328 (4)
O22	0.69889 (18)	0.04450 (9)	0.54522 (6)	0.0268 (3)
O23	0.47889 (17)	0.13768 (9)	0.46577 (5)	0.0251 (3)
H1	1.1048	−0.0919	0.6306	0.025*
H2	0.8969	−0.0502	0.7482	0.025*
H3A	1.1587	0.0761	0.6862	0.030*
H3B	1.0472	0.1050	0.7513	0.030*
H4A	1.1916	−0.0178	0.8144	0.033*
H4B	1.3397	0.0499	0.7796	0.033*
H5A	1.4056	−0.1244	0.7692	0.035*
H5B	1.3912	−0.0713	0.6979	0.035*
H6A	1.2352	−0.2228	0.6931	0.031*
H6B	1.1203	−0.1928	0.7573	0.031*
H12	0.6763	−0.2217	0.6740	0.039*
H13A	0.2647	−0.5280	0.6188	0.050*
H13B	0.1887	−0.4524	0.5640	0.050*
H13C	0.1127	−0.4503	0.6386	0.050*
H14	0.4567	−0.5019	0.5273	0.029*
H15	0.7263	−0.4888	0.4699	0.032*
H16	0.9296	−0.3667	0.4987	0.030*
H17	1.0245	−0.2268	0.5722	0.026*
H22	0.7651	0.0201	0.5747	0.040*
H23A	0.3899	0.2639	0.4262	0.049*
H23B	0.2422	0.1789	0.4326	0.049*
H23C	0.3894	0.1718	0.3754	0.049*
H24	0.2670	0.2628	0.5318	0.030*
H25	0.2652	0.2913	0.6474	0.032*
H26	0.4595	0.2064	0.7167	0.029*
H27	0.6990	0.0824	0.7334	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0219 (8)	0.0205 (8)	0.0189 (7)	−0.0023 (7)	−0.0006 (7)	0.0006 (6)
C2	0.0252 (8)	0.0196 (8)	0.0184 (7)	−0.0009 (7)	−0.0035 (7)	0.0004 (6)
C3	0.0295 (9)	0.0193 (8)	0.0271 (8)	−0.0011 (8)	−0.0052 (8)	−0.0010 (7)
C4	0.0305 (10)	0.0250 (9)	0.0276 (8)	−0.0026 (8)	−0.0101 (8)	−0.0018 (7)
C5	0.0247 (9)	0.0267 (9)	0.0356 (10)	0.0018 (8)	−0.0103 (8)	−0.0019 (8)
C6	0.0301 (10)	0.0206 (8)	0.0276 (8)	0.0020 (8)	−0.0043 (8)	−0.0012 (7)
N11	0.0248 (7)	0.0200 (7)	0.0204 (6)	−0.0020 (6)	−0.0019 (6)	−0.0011 (6)
C11	0.0243 (8)	0.0202 (8)	0.0173 (7)	0.0016 (7)	−0.0043 (7)	−0.0002 (6)
C12	0.0273 (9)	0.0193 (8)	0.0163 (7)	0.0026 (7)	−0.0028 (7)	−0.0020 (6)
C13	0.0236 (8)	0.0217 (8)	0.0209 (7)	0.0000 (7)	−0.0036 (7)	0.0007 (6)
C14	0.0282 (9)	0.0209 (8)	0.0245 (8)	0.0013 (8)	−0.0097 (7)	−0.0032 (6)
C15	0.0312 (9)	0.0266 (9)	0.0221 (8)	0.0070 (8)	−0.0069 (8)	−0.0092 (7)
C16	0.0249 (9)	0.0309 (9)	0.0203 (7)	0.0050 (8)	−0.0015 (7)	−0.0042 (7)
C17	0.0224 (8)	0.0232 (8)	0.0205 (8)	−0.0005 (7)	0.0011 (7)	0.0004 (6)
O12	0.0288 (7)	0.0280 (6)	0.0216 (6)	−0.0068 (6)	0.0048 (5)	−0.0088 (5)
O13	0.0281 (7)	0.0313 (7)	0.0269 (6)	−0.0098 (6)	0.0029 (5)	−0.0069 (5)
N21	0.0229 (7)	0.0213 (7)	0.0207 (6)	−0.0006 (6)	−0.0021 (6)	0.0012 (5)
C21	0.0206 (8)	0.0178 (7)	0.0219 (8)	−0.0042 (7)	0.0010 (6)	0.0005 (6)
C22	0.0194 (8)	0.0172 (7)	0.0224 (7)	−0.0004 (7)	0.0026 (7)	−0.0013 (6)
C23	0.0210 (8)	0.0208 (8)	0.0230 (7)	−0.0026 (7)	−0.0002 (7)	−0.0003 (6)
C24	0.0213 (9)	0.0226 (8)	0.0299 (9)	0.0016 (7)	−0.0021 (7)	0.0029 (7)
C25	0.0270 (9)	0.0218 (8)	0.0324 (9)	0.0055 (8)	0.0050 (8)	−0.0016 (7)
C26	0.0274 (9)	0.0219 (8)	0.0233 (8)	−0.0015 (8)	0.0054 (7)	−0.0019 (7)
C27	0.0242 (8)	0.0203 (8)	0.0190 (7)	−0.0034 (7)	0.0003 (7)	−0.0011 (6)
C131	0.0320 (10)	0.0359 (11)	0.0320 (9)	−0.0114 (9)	−0.0041 (9)	−0.0027 (8)
C231	0.0336 (10)	0.0381 (10)	0.0268 (9)	0.0064 (9)	−0.0097 (8)	0.0029 (8)
O22	0.0269 (7)	0.0326 (7)	0.0210 (5)	0.0116 (6)	−0.0010 (5)	−0.0027 (5)
O23	0.0263 (6)	0.0292 (6)	0.0198 (5)	0.0040 (6)	−0.0041 (5)	−0.0001 (5)

Geometric parameters (Å, º)

C1—N11	1.463 (2)	C27—H27	0.95
C1—C6	1.527 (2)	C21—C26	1.403 (2)
C1—C2	1.530 (2)	C21—C22	1.408 (2)
C1—H1	1.00	C22—O22	1.349 (2)
N11—C17	1.281 (2)	C22—C23	1.405 (2)
C17—C11	1.459 (2)	O22—H22	0.84
C17—H17	0.95	C23—O23	1.3736 (19)
C11—C12	1.400 (3)	C23—C24	1.383 (2)
C11—C16	1.411 (2)	O23—C231	1.431 (2)
C12—O12	1.3504 (19)	C231—H23A	0.98
C12—C13	1.406 (2)	C231—H23B	0.98
O12—H12	0.84	C231—H23C	0.98
C13—O13	1.368 (2)	C24—C25	1.400 (2)
C13—C14	1.390 (2)	C24—H24	0.95
O13—C131	1.428 (2)	C25—C26	1.375 (3)
C131—H13A	0.98	C25—H25	0.95
C131—H13B	0.98	C26—H26	0.95
C131—H13C	0.98	C3—C4	1.528 (3)
C14—C15	1.400 (3)	C3—H3A	0.99
C14—H14	0.95	C3—H3B	0.99
C15—C16	1.373 (3)	C4—C5	1.528 (3)
C15—H15	0.95	C4—H4A	0.99
C16—H16	0.95	C4—H4B	0.99
C2—N21	1.465 (2)	C5—C6	1.529 (3)
C2—C3	1.533 (2)	C5—H5A	0.99
C2—H2	1.00	C5—H5B	0.99
N21—C27	1.278 (2)	C6—H6A	0.99
C27—C21	1.457 (2)	C6—H6B	0.99
N11—C1—C6	111.23 (13)	C22—C21—C27	120.15 (16)
N11—C1—C2	108.74 (14)	O22—C22—C23	118.38 (14)
C6—C1—C2	110.59 (13)	O22—C22—C21	121.96 (15)
N11—C1—H1	108.7	C23—C22—C21	119.64 (15)
C6—C1—H1	108.7	C22—O22—H22	109.5
C2—C1—H1	108.7	O23—C23—C22	114.60 (15)
C17—N11—C1	118.88 (15)	O23—C23—C24	125.37 (15)
N11—C17—C11	121.58 (16)	C24—C23—C22	120.02 (15)
N11—C17—H17	119.2	C23—O23—C231	116.41 (14)
C11—C17—H17	119.2	O23—C231—H23A	109.5
C12—C11—C16	119.36 (16)	O23—C231—H23B	109.5
C12—C11—C17	120.21 (15)	H23A—C231—H23B	109.5
C16—C11—C17	120.41 (16)	O23—C231—H23C	109.5
O12—C12—C11	122.20 (16)	H23A—C231—H23C	109.5
O12—C12—C13	117.81 (16)	H23B—C231—H23C	109.5
C11—C12—C13	119.98 (15)	C23—C24—C25	120.10 (17)
C12—O12—H12	109.5	C23—C24—H24	120.0
O13—C13—C12	115.06 (14)	C25—C24—H24	120.0
O13—C13—C14	125.21 (16)	C26—C25—C24	120.53 (17)
C14—C13—C12	119.72 (17)	C26—C25—H25	119.7
C13—O13—C131	116.97 (14)	C24—C25—H25	119.7
O13—C131—H13A	109.5	C25—C26—C21	120.26 (16)
O13—C131—H13B	109.5	C25—C26—H26	119.9
H13A—C131—H13B	109.5	C21—C26—H26	119.9
O13—C131—H13C	109.5	C4—C3—C2	111.48 (14)
H13A—C131—H13C	109.5	C4—C3—H3A	109.3
H13B—C131—H13C	109.5	C2—C3—H3A	109.3
C13—C14—C15	120.14 (17)	C4—C3—H3B	109.3
C13—C14—H14	119.9	C2—C3—H3B	109.3
C15—C14—H14	119.9	H3A—C3—H3B	108.0
C16—C15—C14	120.51 (16)	C3—C4—C5	111.26 (14)
C16—C15—H15	119.7	C3—C4—H4A	109.4
C14—C15—H15	119.7	C5—C4—H4A	109.4
C15—C16—C11	120.26 (17)	C3—C4—H4B	109.4
C15—C16—H16	119.9	C5—C4—H4B	109.4
C11—C16—H16	119.9	H4A—C4—H4B	108.0
N21—C2—C1	109.15 (13)	C4—C5—C6	112.03 (16)
N21—C2—C3	109.93 (13)	C4—C5—H5A	109.2
C1—C2—C3	110.08 (15)	C6—C5—H5A	109.2
N21—C2—H2	109.2	C4—C5—H5B	109.2
C1—C2—H2	109.2	C6—C5—H5B	109.2
C3—C2—H2	109.2	H5A—C5—H5B	107.9
C27—N21—C2	119.63 (14)	C1—C6—C5	110.43 (14)
N21—C27—C21	121.30 (15)	C1—C6—H6A	109.6
N21—C27—H27	119.4	C5—C6—H6A	109.6
C21—C27—H27	119.4	C1—C6—H6B	109.6
C26—C21—C22	119.45 (16)	C5—C6—H6B	109.6
C26—C21—C27	120.38 (15)	H6A—C6—H6B	108.1
C6—C1—N11—C17	−91.25 (18)	C2—N21—C27—C21	177.82 (15)
C2—C1—N11—C17	146.74 (15)	N21—C27—C21—C26	−172.42 (16)
C1—N11—C17—C11	178.86 (14)	N21—C27—C21—C22	6.1 (2)
N11—C17—C11—C12	6.8 (2)	C26—C21—C22—O22	178.55 (15)
N11—C17—C11—C16	−171.31 (16)	C27—C21—C22—O22	0.0 (2)
C16—C11—C12—O12	179.26 (15)	C26—C21—C22—C23	0.3 (2)
C17—C11—C12—O12	1.1 (2)	C27—C21—C22—C23	−178.29 (15)
C16—C11—C12—C13	0.3 (2)	O22—C22—C23—O23	0.6 (2)
C17—C11—C12—C13	−177.84 (15)	C21—C22—C23—O23	178.98 (15)
O12—C12—C13—O13	1.0 (2)	O22—C22—C23—C24	−178.15 (15)
C11—C12—C13—O13	179.97 (15)	C21—C22—C23—C24	0.2 (3)
O12—C12—C13—C14	−177.73 (15)	C24—C23—O23—C231	1.8 (2)
C11—C12—C13—C14	1.2 (2)	C22—C23—O23—C231	−176.88 (15)
C14—C13—O13—C131	−1.7 (2)	O23—C23—C24—C25	−179.07 (17)
C12—C13—O13—C131	179.67 (15)	C22—C23—C24—C25	−0.4 (3)
O13—C13—C14—C15	−179.85 (16)	C23—C24—C25—C26	0.2 (3)
C12—C13—C14—C15	−1.3 (2)	C24—C25—C26—C21	0.3 (3)
C13—C14—C15—C16	−0.3 (3)	C22—C21—C26—C25	−0.5 (3)
C14—C15—C16—C11	1.9 (3)	C27—C21—C26—C25	178.04 (16)
C12—C11—C16—C15	−1.9 (2)	N21—C2—C3—C4	−176.99 (14)
C17—C11—C16—C15	176.25 (16)	C1—C2—C3—C4	−56.73 (19)
N11—C1—C2—N21	−58.28 (17)	C2—C3—C4—C5	54.1 (2)
C6—C1—C2—N21	179.32 (14)	C3—C4—C5—C6	−53.5 (2)
N11—C1—C2—C3	−179.02 (13)	N11—C1—C6—C5	−178.80 (14)
C6—C1—C2—C3	58.58 (18)	C2—C1—C6—C5	−57.87 (19)
C1—C2—N21—C27	158.41 (15)	C4—C5—C6—C1	55.4 (2)
C3—C2—N21—C27	−80.76 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···N11	0.84	1.84	2.580 (2)	147
O22—H22···N21	0.84	1.82	2.568 (2)	147
C14—H14···O22^i	0.95	2.50	3.329 (2)	146
C24—H24···O23^ii	0.95	2.55	3.356 (2)	142
C26—H26···O12^iii	0.95	2.45	3.398 (2)	172

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