2,6-Bis(1H-imidazol-1-ylmeth­yl)pyridine sesquihydrate

The title compound, C₁₃H₁₃N₅·1.5H₂O, was synthesized by the reaction of 2,6-bis­(bromo­meth­yl)pyridine with imidazole. The asymmetric unit contains two crystallographically independent 2,6-bis­(1H-imidazol-1-ylmeth­yl)pyridine mol­ecules and three water mol­ecules. The crystal packing is stabilized by O—H...O and O—H...N hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.148
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N9

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Bruker, 1999); software used to prepare material for publication: SHELXTL.

2,6-Bis(1H-imidazol-1-ylmethyl)pyridine 1.5-hydrate

Crystal data

C13H13N5·1.5H2O	Z = 4
Mr = 266.31	F(000) = 564
Triclinic, P1	Dx = 1.273 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.260 (2) Å	Cell parameters from 1781 reflections
b = 10.846 (3) Å	θ = 2.3–25.8°
c = 15.531 (4) Å	µ = 0.09 mm^−1
α = 77.794 (4)°	T = 294 K
β = 87.324 (4)°	Block, colourless
γ = 65.873 (4)°	0.22 × 0.20 × 0.16 mm
V = 1390.0 (6) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	5600 independent reflections
Radiation source: fine-focus sealed tube	2796 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→11
Tmin = 0.972, Tmax = 0.986	k = −9→13
7869 measured reflections	l = −19→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.1192P] where P = (Fo^2 + 2Fc^2)/3
5600 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.17 e Å^−3
9 restraints	Δρmin = −0.18 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
N1	0.5707 (3)	0.8598 (2)	0.38487 (15)	0.0855 (7)
N2	0.6516 (2)	0.82449 (17)	0.52253 (13)	0.0547 (5)
N3	0.7084 (2)	0.54625 (18)	0.69742 (10)	0.0444 (4)
N4	0.7450 (2)	0.31854 (18)	0.87550 (11)	0.0449 (4)
N5	0.8316 (3)	0.2319 (3)	1.01430 (13)	0.0728 (6)
N6	0.1692 (2)	0.7548 (2)	0.48510 (12)	0.0602 (5)
N7	0.2599 (2)	0.68377 (17)	0.62362 (10)	0.0435 (4)
N8	0.2763 (2)	0.46802 (17)	0.79627 (10)	0.0426 (4)
N9	0.3466 (2)	0.19049 (18)	0.96316 (12)	0.0524 (5)
N10	0.3513 (3)	0.0929 (2)	1.10282 (15)	0.0826 (7)
C1	0.6822 (4)	0.9098 (3)	0.3876 (2)	0.0890 (10)
H1	0.7184	0.9527	0.3384	0.107*
C2	0.7330 (3)	0.8890 (2)	0.4704 (2)	0.0784 (9)
H2	0.8095	0.9139	0.4890	0.094*
C3	0.5565 (3)	0.8101 (3)	0.46761 (18)	0.0680 (7)
H3	0.4868	0.7687	0.4862	0.082*
C4	0.6681 (3)	0.7753 (2)	0.61750 (15)	0.0666 (7)
H4A	0.5641	0.7925	0.6407	0.080*
H4B	0.7123	0.8271	0.6432	0.080*
C5	0.7729 (3)	0.6231 (2)	0.64475 (13)	0.0450 (5)
C6	0.9258 (3)	0.5680 (2)	0.61646 (14)	0.0503 (6)
H6	0.9667	0.6242	0.5795	0.060*
C7	1.0161 (3)	0.4290 (2)	0.64390 (14)	0.0511 (6)
H7	1.1193	0.3896	0.6259	0.061*
C8	0.9518 (3)	0.3490 (2)	0.69837 (13)	0.0463 (5)
H8	1.0110	0.2547	0.7181	0.056*
C9	0.7981 (3)	0.4106 (2)	0.72331 (12)	0.0404 (5)
C10	0.7205 (3)	0.3271 (2)	0.78168 (13)	0.0512 (6)
H10A	0.6077	0.3688	0.7668	0.061*
H10B	0.7631	0.2344	0.7703	0.061*
C11	0.6827 (3)	0.4240 (2)	0.91904 (15)	0.0537 (6)
H11	0.6164	0.5154	0.8953	0.064*
C12	0.7363 (3)	0.3694 (3)	1.00334 (16)	0.0656 (7)
H12	0.7118	0.4187	1.0482	0.079*
C13	0.8337 (3)	0.2057 (3)	0.93531 (16)	0.0607 (7)
H13	0.8900	0.1190	0.9223	0.073*
C14	0.2719 (3)	0.6193 (3)	0.49953 (15)	0.0585 (6)
H14	0.2992	0.5655	0.4571	0.070*
C15	0.3284 (3)	0.5743 (2)	0.58405 (14)	0.0534 (6)
H15	0.4001	0.4858	0.6101	0.064*
C16	0.1647 (3)	0.7896 (2)	0.56154 (15)	0.0522 (6)
H16	0.1028	0.8772	0.5716	0.063*
C17	0.2767 (3)	0.6847 (2)	0.71655 (12)	0.0486 (6)
H17A	0.2320	0.7794	0.7243	0.058*
H17B	0.3883	0.6439	0.7344	0.058*
C18	0.1940 (3)	0.6049 (2)	0.77440 (12)	0.0412 (5)
C19	0.0426 (3)	0.6705 (2)	0.80144 (14)	0.0501 (6)
H19	−0.0121	0.7658	0.7844	0.060*
C20	−0.0262 (3)	0.5920 (3)	0.85412 (14)	0.0578 (6)
H20	−0.1277	0.6338	0.8736	0.069*
C21	0.0571 (3)	0.4517 (2)	0.87735 (14)	0.0551 (6)
H21	0.0134	0.3969	0.9133	0.066*
C22	0.2073 (3)	0.3927 (2)	0.84649 (13)	0.0460 (5)
C23	0.3030 (3)	0.2385 (2)	0.86931 (14)	0.0619 (7)
H23A	0.2415	0.1922	0.8530	0.074*
H23B	0.3981	0.2150	0.8359	0.074*
C24	0.4511 (3)	0.2161 (3)	1.00734 (18)	0.0717 (8)
H24	0.5097	0.2663	0.9836	0.086*
C25	0.4527 (3)	0.1549 (3)	1.0919 (2)	0.0818 (8)
H25	0.5153	0.1552	1.1369	0.098*
C26	0.2904 (3)	0.1165 (3)	1.02357 (18)	0.0723 (8)
H26	0.2160	0.0851	1.0108	0.087*
O1	0.0379 (2)	0.96632 (18)	0.32922 (12)	0.0772 (6)
H1A	0.121 (2)	0.981 (3)	0.3087 (17)	0.116*
H1B	0.063 (3)	0.898 (2)	0.3738 (13)	0.116*
O2	0.8566 (3)	0.0127 (2)	0.17209 (14)	0.0983 (7)
H2A	0.919 (3)	−0.002 (3)	0.2159 (13)	0.147*
H2B	0.862 (4)	0.075 (3)	0.1284 (13)	0.147*
O3	0.3079 (3)	0.9681 (3)	0.26694 (13)	0.1198 (9)
H3A	0.315 (4)	1.009 (4)	0.2137 (10)	0.180*
H3B	0.397 (2)	0.921 (4)	0.2962 (19)	0.180*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0831 (18)	0.0848 (17)	0.0636 (16)	−0.0175 (15)	−0.0023 (13)	0.0020 (13)
N2	0.0511 (12)	0.0417 (11)	0.0611 (13)	−0.0176 (10)	−0.0002 (10)	0.0078 (9)
N3	0.0475 (11)	0.0500 (11)	0.0361 (10)	−0.0199 (9)	0.0011 (8)	−0.0097 (8)
N4	0.0506 (11)	0.0505 (11)	0.0362 (10)	−0.0262 (9)	0.0037 (8)	−0.0034 (9)
N5	0.0720 (15)	0.1003 (19)	0.0441 (13)	−0.0423 (14)	−0.0055 (11)	0.0055 (12)
N6	0.0671 (14)	0.0726 (15)	0.0413 (12)	−0.0346 (12)	−0.0024 (10)	0.0008 (10)
N7	0.0480 (11)	0.0454 (10)	0.0365 (10)	−0.0207 (9)	0.0028 (8)	−0.0043 (9)
N8	0.0480 (11)	0.0454 (11)	0.0337 (10)	−0.0192 (9)	0.0000 (8)	−0.0065 (8)
N9	0.0524 (12)	0.0490 (11)	0.0520 (12)	−0.0228 (10)	0.0001 (10)	0.0021 (9)
N10	0.0810 (17)	0.0821 (16)	0.0613 (16)	−0.0245 (14)	−0.0007 (13)	0.0160 (12)
C1	0.063 (2)	0.0639 (18)	0.092 (2)	−0.0006 (16)	0.0205 (18)	0.0252 (16)
C2	0.0551 (17)	0.0559 (16)	0.110 (2)	−0.0251 (14)	−0.0019 (17)	0.0187 (16)
C3	0.0619 (17)	0.0700 (17)	0.0669 (19)	−0.0294 (14)	0.0022 (14)	0.0012 (14)
C4	0.0816 (19)	0.0451 (14)	0.0604 (16)	−0.0155 (13)	0.0025 (14)	−0.0060 (12)
C5	0.0539 (15)	0.0443 (12)	0.0365 (12)	−0.0199 (12)	0.0007 (11)	−0.0079 (10)
C6	0.0589 (15)	0.0493 (13)	0.0461 (13)	−0.0286 (12)	0.0066 (11)	−0.0044 (11)
C7	0.0475 (14)	0.0536 (14)	0.0504 (14)	−0.0195 (12)	0.0047 (11)	−0.0104 (11)
C8	0.0514 (14)	0.0409 (12)	0.0431 (13)	−0.0160 (11)	−0.0017 (11)	−0.0066 (10)
C9	0.0523 (14)	0.0457 (12)	0.0281 (11)	−0.0249 (11)	−0.0032 (10)	−0.0066 (9)
C10	0.0647 (15)	0.0585 (14)	0.0420 (13)	−0.0363 (13)	0.0040 (11)	−0.0117 (11)
C11	0.0578 (15)	0.0612 (15)	0.0481 (15)	−0.0284 (13)	0.0095 (12)	−0.0170 (12)
C12	0.0676 (18)	0.096 (2)	0.0479 (16)	−0.0451 (17)	0.0084 (13)	−0.0219 (15)
C13	0.0600 (16)	0.0590 (15)	0.0566 (16)	−0.0246 (13)	0.0019 (13)	0.0020 (13)
C14	0.0599 (16)	0.0729 (18)	0.0456 (15)	−0.0280 (14)	0.0081 (12)	−0.0180 (13)
C15	0.0491 (14)	0.0564 (15)	0.0481 (15)	−0.0140 (12)	0.0020 (11)	−0.0132 (12)
C16	0.0534 (15)	0.0474 (13)	0.0516 (15)	−0.0227 (12)	0.0002 (11)	0.0031 (11)
C17	0.0604 (15)	0.0512 (13)	0.0383 (13)	−0.0274 (12)	0.0001 (10)	−0.0077 (10)
C18	0.0499 (14)	0.0466 (13)	0.0293 (11)	−0.0214 (11)	−0.0034 (10)	−0.0083 (9)
C19	0.0500 (15)	0.0460 (13)	0.0472 (13)	−0.0130 (12)	−0.0025 (11)	−0.0081 (11)
C20	0.0446 (14)	0.0719 (17)	0.0548 (15)	−0.0206 (13)	0.0084 (12)	−0.0167 (13)
C21	0.0572 (16)	0.0642 (16)	0.0496 (14)	−0.0334 (14)	0.0068 (12)	−0.0067 (12)
C22	0.0564 (15)	0.0498 (13)	0.0343 (12)	−0.0251 (12)	−0.0023 (11)	−0.0061 (10)
C23	0.0823 (18)	0.0498 (14)	0.0502 (15)	−0.0265 (14)	0.0040 (13)	−0.0048 (11)
C24	0.0583 (17)	0.0831 (19)	0.080 (2)	−0.0389 (15)	−0.0020 (15)	−0.0080 (16)
C25	0.068 (2)	0.089 (2)	0.071 (2)	−0.0193 (17)	−0.0172 (16)	−0.0043 (16)
C26	0.0719 (18)	0.0685 (17)	0.0721 (19)	−0.0379 (15)	−0.0052 (15)	0.0149 (14)
O1	0.0873 (14)	0.0611 (11)	0.0639 (12)	−0.0194 (11)	−0.0045 (10)	0.0055 (9)
O2	0.1242 (19)	0.0811 (14)	0.0852 (15)	−0.0464 (14)	−0.0254 (13)	0.0069 (11)
O3	0.1160 (18)	0.180 (2)	0.0722 (14)	−0.0942 (19)	−0.0129 (13)	0.0295 (14)

Geometric parameters (Å, º)

N1—C3	1.307 (3)	C8—C9	1.379 (3)
N1—C1	1.354 (4)	C8—H8	0.9300
N2—C3	1.330 (3)	C9—C10	1.511 (3)
N2—C2	1.360 (3)	C10—H10A	0.9700
N2—C4	1.451 (3)	C10—H10B	0.9700
N3—C5	1.339 (3)	C11—C12	1.343 (3)
N3—C9	1.341 (2)	C11—H11	0.9300
N4—C13	1.343 (3)	C12—H12	0.9300
N4—C11	1.360 (3)	C13—H13	0.9300
N4—C10	1.463 (2)	C14—C15	1.349 (3)
N5—C13	1.314 (3)	C14—H14	0.9300
N5—C12	1.365 (3)	C15—H15	0.9300
N6—C16	1.313 (3)	C16—H16	0.9300
N6—C14	1.361 (3)	C17—C18	1.514 (3)
N7—C16	1.345 (2)	C17—H17A	0.9700
N7—C15	1.359 (2)	C17—H17B	0.9700
N7—C17	1.461 (2)	C18—C19	1.380 (3)
N8—C18	1.336 (2)	C19—C20	1.378 (3)
N8—C22	1.340 (3)	C19—H19	0.9300
N9—C26	1.331 (3)	C20—C21	1.370 (3)
N9—C24	1.359 (3)	C20—H20	0.9300
N9—C23	1.456 (3)	C21—C22	1.383 (3)
N10—C26	1.308 (3)	C21—H21	0.9300
N10—C25	1.348 (3)	C22—C23	1.508 (3)
C1—C2	1.331 (4)	C23—H23A	0.9700
C1—H1	0.9300	C23—H23B	0.9700
C2—H2	0.9300	C24—C25	1.337 (3)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.510 (3)	C25—H25	0.9300
C4—H4A	0.9700	C26—H26	0.9300
C4—H4B	0.9700	O1—H1A	0.876 (10)
C5—C6	1.385 (3)	O1—H1B	0.86 (2)
C6—C7	1.372 (3)	O2—H2A	0.86 (2)
C6—H6	0.9300	O2—H2B	0.87 (3)
C7—C8	1.375 (3)	O3—H3A	0.864 (10)
C7—H7	0.9300	O3—H3B	0.86 (3)
C3—N1—C1	104.0 (3)	N4—C11—H11	127.0
C3—N2—C2	105.4 (2)	C11—C12—N5	110.8 (2)
C3—N2—C4	126.4 (2)	C11—C12—H12	124.6
C2—N2—C4	128.1 (2)	N5—C12—H12	124.6
C5—N3—C9	117.51 (18)	N5—C13—N4	112.1 (2)
C13—N4—C11	106.63 (19)	N5—C13—H13	123.9
C13—N4—C10	126.9 (2)	N4—C13—H13	123.9
C11—N4—C10	126.51 (18)	C15—C14—N6	110.4 (2)
C13—N5—C12	104.3 (2)	C15—C14—H14	124.8
C16—N6—C14	104.73 (19)	N6—C14—H14	124.8
C16—N7—C15	106.35 (18)	C14—C15—N7	106.4 (2)
C16—N7—C17	126.42 (19)	C14—C15—H15	126.8
C15—N7—C17	127.10 (18)	N7—C15—H15	126.8
C18—N8—C22	117.90 (18)	N6—C16—N7	112.2 (2)
C26—N9—C24	105.9 (2)	N6—C16—H16	123.9
C26—N9—C23	127.7 (2)	N7—C16—H16	123.9
C24—N9—C23	126.4 (2)	N7—C17—C18	111.27 (16)
C26—N10—C25	104.4 (2)	N7—C17—H17A	109.4
C2—C1—N1	110.6 (3)	C18—C17—H17A	109.4
C2—C1—H1	124.7	N7—C17—H17B	109.4
N1—C1—H1	124.7	C18—C17—H17B	109.4
C1—C2—N2	106.8 (3)	H17A—C17—H17B	108.0
C1—C2—H2	126.6	N8—C18—C19	122.8 (2)
N2—C2—H2	126.6	N8—C18—C17	115.68 (19)
N1—C3—N2	113.2 (3)	C19—C18—C17	121.5 (2)
N1—C3—H3	123.4	C20—C19—C18	118.8 (2)
N2—C3—H3	123.4	C20—C19—H19	120.6
N2—C4—C5	112.72 (18)	C18—C19—H19	120.6
N2—C4—H4A	109.0	C21—C20—C19	119.1 (2)
C5—C4—H4A	109.0	C21—C20—H20	120.5
N2—C4—H4B	109.0	C19—C20—H20	120.5
C5—C4—H4B	109.0	C20—C21—C22	119.0 (2)
H4A—C4—H4B	107.8	C20—C21—H21	120.5
N3—C5—C6	122.8 (2)	C22—C21—H21	120.5
N3—C5—C4	115.8 (2)	N8—C22—C21	122.5 (2)
C6—C5—C4	121.4 (2)	N8—C22—C23	116.5 (2)
C7—C6—C5	118.9 (2)	C21—C22—C23	121.0 (2)
C7—C6—H6	120.6	N9—C23—C22	111.18 (18)
C5—C6—H6	120.6	N9—C23—H23A	109.4
C6—C7—C8	119.0 (2)	C22—C23—H23A	109.4
C6—C7—H7	120.5	N9—C23—H23B	109.4
C8—C7—H7	120.5	C22—C23—H23B	109.4
C7—C8—C9	119.0 (2)	H23A—C23—H23B	108.0
C7—C8—H8	120.5	C25—C24—N9	106.3 (2)
C9—C8—H8	120.5	C25—C24—H24	126.8
N3—C9—C8	122.85 (19)	N9—C24—H24	126.8
N3—C9—C10	115.95 (19)	C24—C25—N10	110.7 (3)
C8—C9—C10	121.2 (2)	C24—C25—H25	124.6
N4—C10—C9	112.58 (16)	N10—C25—H25	124.6
N4—C10—H10A	109.1	N10—C26—N9	112.7 (2)
C9—C10—H10A	109.1	N10—C26—H26	123.6
N4—C10—H10B	109.1	N9—C26—H26	123.6
C9—C10—H10B	109.1	H1A—O1—H1B	111.7 (15)
H10A—C10—H10B	107.8	H2A—O2—H2B	112.0 (16)
C12—C11—N4	106.1 (2)	H3A—O3—H3B	114.6 (18)
C12—C11—H11	127.0
C3—N1—C1—C2	0.3 (3)	C16—N6—C14—C15	−0.2 (3)
N1—C1—C2—N2	−0.3 (3)	N6—C14—C15—N7	0.0 (3)
C3—N2—C2—C1	0.1 (3)	C16—N7—C15—C14	0.3 (2)
C4—N2—C2—C1	177.6 (2)	C17—N7—C15—C14	176.32 (19)
C1—N1—C3—N2	−0.3 (3)	C14—N6—C16—N7	0.4 (2)
C2—N2—C3—N1	0.1 (3)	C15—N7—C16—N6	−0.5 (2)
C4—N2—C3—N1	−177.4 (2)	C17—N7—C16—N6	−176.53 (18)
C3—N2—C4—C5	79.8 (3)	C16—N7—C17—C18	105.2 (2)
C2—N2—C4—C5	−97.1 (3)	C15—N7—C17—C18	−70.0 (3)
C9—N3—C5—C6	0.3 (3)	C22—N8—C18—C19	0.1 (3)
C9—N3—C5—C4	−179.72 (18)	C22—N8—C18—C17	−179.18 (16)
N2—C4—C5—N3	−124.9 (2)	N7—C17—C18—N8	82.9 (2)
N2—C4—C5—C6	55.1 (3)	N7—C17—C18—C19	−96.4 (2)
N3—C5—C6—C7	−0.5 (3)	N8—C18—C19—C20	0.8 (3)
C4—C5—C6—C7	179.5 (2)	C17—C18—C19—C20	−179.93 (18)
C5—C6—C7—C8	0.2 (3)	C18—C19—C20—C21	−0.5 (3)
C6—C7—C8—C9	0.4 (3)	C19—C20—C21—C22	−0.6 (3)
C5—N3—C9—C8	0.3 (3)	C18—N8—C22—C21	−1.3 (3)
C5—N3—C9—C10	−179.21 (16)	C18—N8—C22—C23	179.50 (17)
C7—C8—C9—N3	−0.7 (3)	C20—C21—C22—N8	1.6 (3)
C7—C8—C9—C10	178.83 (18)	C20—C21—C22—C23	−179.3 (2)
C13—N4—C10—C9	−111.1 (2)	C26—N9—C23—C22	108.6 (3)
C11—N4—C10—C9	68.5 (3)	C24—N9—C23—C22	−69.3 (3)
N3—C9—C10—N4	−90.5 (2)	N8—C22—C23—N9	112.5 (2)
C8—C9—C10—N4	90.0 (2)	C21—C22—C23—N9	−66.6 (3)
C13—N4—C11—C12	−0.3 (2)	C26—N9—C24—C25	0.5 (3)
C10—N4—C11—C12	−179.97 (19)	C23—N9—C24—C25	178.9 (2)
N4—C11—C12—N5	0.2 (3)	N9—C24—C25—N10	−0.8 (3)
C13—N5—C12—C11	0.0 (3)	C26—N10—C25—C24	0.7 (3)
C12—N5—C13—N4	−0.2 (3)	C25—N10—C26—N9	−0.3 (3)
C11—N4—C13—N5	0.3 (3)	C24—N9—C26—N10	−0.1 (3)
C10—N4—C13—N5	179.97 (18)	C23—N9—C26—N10	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.88 (1)	1.78 (1)	2.644 (3)	166 (3)
O1—H1B···N6	0.86 (2)	2.03 (1)	2.872 (2)	165 (2)
O2—H2A···O1^i	0.86 (2)	2.01 (1)	2.864 (3)	171 (3)
O2—H2B···N5^ii	0.87 (3)	2.12 (1)	2.975 (3)	169 (3)
O3—H3A···N10^iii	0.86 (1)	1.86 (1)	2.717 (3)	174 (3)
O3—H3B···N1	0.86 (3)	1.97 (2)	2.797 (3)	162 (4)

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