1,4-Bis[1-(pyridin-4-ylmeth­yl)-1H-benz­imidazol-2-yl]butane dihydrate

Li, S.-L.; Liu, J.; Ma, J.-F.

doi:10.1107/S1600536807053949

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1,4-Bis[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]butane dihydrate

S.-L. Li, J. Liu and J.-F. Ma

The title compound, C₃₀H₂₈N₆·2H₂O, is an example of a new N-donor neutral organic ligand. The asymmetric unit consists of two half-molecules (organic) and two water molecules; each independent organic molecule is centrosymmetric. The water molecules are linked by O—H

O hydrogen bonds, forming infinite chains stretching parallel to the a axis. These water chains also link the molecules of the title compound via C—H

O and O—H

N hydrogen bonds, generating a two-dimensional supramolecular layer-like structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053949/zl2075sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053949/zl2075Isup2.hkl Contains datablock I

CCDC reference: 672790

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.060
wR factor = 0.137
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.27
           From the CIF: _reflns_number_total               6112
           From the CIF: _diffrn_reflns_limit_ max hkl    6.   35.   21.
           From the CIF: _diffrn_reflns_limit_ min hkl   -6.  -34.  -24.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl    6.   37.   25.
           Calculated minimum hkl   -6.  -37.  -25.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The research on coordination polymers exhibiting novel structures and properties is an attractive field (Leininger et al., 2000). The key factor for construction of coordination polymers is the selection of the organic ligand. Among various organic ligands, flexible N-donor ligands are beneficial when trying to form helical and interpenetrating structures (Chesnut et al., 1999; Chu et al., 2007; Liu & Tilley 1997; Lo et al., 2000; Tong et al., 1999). In this paper, we describe the isolation and structural characterization of a new N-donor neutral ligand, 1,4-bis(1-(pyridin-4-ylmethyl)-1H-benzo[d]imidazol-2-yl)butane (hereafter L).

The asymmetric part of the unit cell contains two crystallographically independent L molecules located each on an inversion center and two water molecules (Fig. 1). The butyl groups in different L molecules display TTT (T = trans) conformations. The dihedral angles between the phenyl and pyridine rings are 82.2 and 106.2°, respectively, in the two different L molceules. The water molecules are linked by O—H···O bonds to form an infinite water chain along the a axis. In addition, the water molecules in the water chains donate hydrogen bonds to N atoms of L molecules, and L molecules donate C—H···O bonds to water molecules. So the water chains link all L molecules along the c axis to generate a two dimensional supramolecular layerlike structure (Fig. 2). The sheet is waved and parallel to the a,c plane (Fig. 3).

Related literature top

For related literature about coordination polymers, see: Leininger et al. (2000). For related literature about flexible neutral N-donor ligands related to the title compound and their ability to form helical and interpenetrating structures, see: Chesnut et al. (1999); Chu et al. (2007); Liu & Tilley (1997); Lo et al. (2000); Tong et al. (1999). For the synthesis of 1,4-bis(benzimidazol-2-yl)butane, see: (Chen et al. (2002).

Experimental top

A mixture of 1,4-bis(benzimidazol-2-yl)butane (Chen et al., 2002) (2.90 g, 10 mmol) and NaOH (0.80 g, 20 mmol) in DMSO (30 ml) was stirred at 60°C for 1 h, then 4-(chloromethyl)pyridine (5.10 g, 40 mmol) was added. The mixture was cooled to room temperature after stirring at 60°C for 24 h, and then poured into 200 ml of water. A colorless solid of L formed immediately, which was isolated by filtration in 65% yield after drying in air. Crystals suitable for X-ray diffraction were grown from 70% ethanol.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. A view of the title molecule. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Symmetry codes: (iv) 3 - x, 1 - y, 2 - z; (v) 2 - x, 1 - y, 1 - z.
	Fig. 3. and 3. View of two dimensional supramolecular layerlike strucutre of the title molecule along different directions. Green dashed lines represent O—H···O hydrogen bonds within the water chains, gray dashed lines represent of C—H···O bonds. All H atoms except H1A, H1B and H13 are omitted for clarity.

1,4-Bis[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]butane dihydrate top

Crystal data top

C₃₀H₂₈N₆·2H₂O	Z = 4
M_r = 508.62	F(000) = 1080
Monoclinic, P2₁/n	D_x = 1.285 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 4.9430 (2) Å	θ = 1.8–28.3°
b = 27.969 (5) Å	µ = 0.08 mm⁻¹
c = 19.042 (5) Å	T = 293 K
β = 93.295 (5)°	Block, colorless
V = 2628.2 (8) Å³	0.35 × 0.32 × 0.28 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	6112 independent reflections
Radiation source: fine-focus sealed tube	2470 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −6→6
T_min = 0.971, T_max = 0.977	k = −34→35
16155 measured reflections	l = −24→21

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
6112 reflections	(Δ/σ)_max < 0.001
355 parameters	Δρ_max = 0.16 e Å⁻³
6 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₀H₂₈N₆·2H₂O	V = 2628.2 (8) Å³
M_r = 508.62	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.9430 (2) Å	µ = 0.08 mm⁻¹
b = 27.969 (5) Å	T = 293 K
c = 19.042 (5) Å	0.35 × 0.32 × 0.28 mm
β = 93.295 (5)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6112 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	2470 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.977	R_int = 0.065
16155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	6 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.16 e Å⁻³
6112 reflections	Δρ_min = −0.24 e Å⁻³
355 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.8933 (5)	0.50658 (8)	0.47192 (11)	0.0472 (6)
H1	0.9561	0.5336	0.4453	0.057*
H2	0.7298	0.5163	0.4939	0.057*
C2	0.8277 (5)	0.46522 (8)	0.42202 (12)	0.0486 (7)
H3	0.9911	0.4562	0.3995	0.058*
H4	0.7709	0.4380	0.4491	0.058*
C3	0.6115 (5)	0.47634 (9)	0.36662 (12)	0.0444 (6)
C4	0.2902 (5)	0.51006 (9)	0.30361 (12)	0.0468 (6)
C5	0.0874 (6)	0.54023 (10)	0.27606 (13)	0.0584 (7)
H5	0.0467	0.5687	0.2983	0.070*
C6	−0.0516 (6)	0.52635 (11)	0.21446 (15)	0.0687 (8)
H6	−0.1882	0.5459	0.1948	0.082*
C7	0.0090 (6)	0.48374 (11)	0.18125 (14)	0.0662 (8)
H7	−0.0877	0.4757	0.1396	0.079*
C8	0.2062 (6)	0.45308 (10)	0.20766 (13)	0.0573 (7)
H8	0.2455	0.4246	0.1852	0.069*
C9	0.3437 (5)	0.46709 (9)	0.27001 (12)	0.0455 (6)
C10	0.6533 (5)	0.39772 (9)	0.30030 (13)	0.0566 (7)
H10A	0.8251	0.3940	0.3270	0.068*
H10B	0.6853	0.3935	0.2509	0.068*
C11	0.4576 (5)	0.35964 (9)	0.32270 (14)	0.0518 (7)
C12	0.3915 (6)	0.35553 (10)	0.39164 (16)	0.0730 (9)
H12	0.4690	0.3762	0.4253	0.088*
C13	0.2124 (7)	0.32119 (11)	0.41118 (16)	0.0839 (10)
H13	0.1733	0.3192	0.4583	0.101*
C14	0.1546 (7)	0.29493 (11)	0.29927 (18)	0.0778 (9)
H14	0.0726	0.2740	0.2665	0.093*
C15	0.3333 (6)	0.32844 (10)	0.27557 (15)	0.0662 (8)
H15	0.3689	0.3298	0.2282	0.079*
C16	0.4202 (5)	0.47921 (8)	0.01279 (13)	0.0568 (7)
H16A	0.2286	0.4860	0.0046	0.068*
H16B	0.4571	0.4759	0.0631	0.068*
C17	0.4827 (6)	0.43240 (9)	−0.02227 (13)	0.0630 (8)
H17A	0.4378	0.4353	−0.0723	0.076*
H17B	0.6759	0.4264	−0.0160	0.076*
C18	0.3344 (6)	0.39059 (9)	0.00522 (13)	0.0533 (7)
C19	0.0803 (6)	0.34537 (10)	0.06411 (13)	0.0563 (7)
C20	−0.1044 (6)	0.32642 (12)	0.10847 (15)	0.0758 (9)
H20	−0.2057	0.3462	0.1361	0.091*
C21	−0.1343 (7)	0.27759 (14)	0.11065 (16)	0.0844 (10)
H21	−0.2585	0.2643	0.1399	0.101*
C22	0.0181 (7)	0.24777 (12)	0.06990 (18)	0.0843 (10)
H22	−0.0031	0.2148	0.0734	0.101*
C23	0.1984 (6)	0.26558 (11)	0.02472 (16)	0.0736 (9)
H23	0.2973	0.2456	−0.0033	0.088*
C24	0.2264 (6)	0.31486 (10)	0.02284 (14)	0.0555 (7)
C25	0.5705 (6)	0.32965 (9)	−0.06941 (14)	0.0639 (8)
H25A	0.6288	0.2971	−0.0595	0.077*
H25B	0.7302	0.3499	−0.0666	0.077*
C26	0.2227 (6)	0.30358 (10)	−0.16366 (16)	0.0681 (8)
H26	0.1473	0.2829	−0.1319	0.082*
C27	0.4421 (6)	0.33192 (9)	−0.14281 (14)	0.0549 (7)
C28	0.5399 (6)	0.36186 (10)	−0.19213 (16)	0.0721 (9)
H28	0.6857	0.3819	−0.1804	0.087*
C29	0.4197 (8)	0.36214 (12)	−0.25995 (18)	0.0842 (10)
H29	0.4892	0.3828	−0.2927	0.101*
C30	0.1172 (7)	0.30636 (11)	−0.23204 (18)	0.0759 (9)
H30	−0.0305	0.2871	−0.2450	0.091*
N1	0.1506 (5)	0.39272 (8)	0.05213 (11)	0.0595 (6)
N2	0.3876 (4)	0.34486 (7)	−0.01566 (11)	0.0540 (6)
N3	0.0923 (5)	0.29067 (9)	0.36614 (16)	0.0804 (8)
N4	0.5492 (4)	0.44589 (7)	0.31133 (10)	0.0459 (5)
N5	0.4621 (4)	0.51524 (7)	0.36370 (10)	0.0469 (5)
N6	0.2121 (6)	0.33468 (10)	−0.28065 (13)	0.0762 (7)
O1W	0.5470 (4)	0.39740 (7)	0.55905 (10)	0.0684 (6)
O2W	0.0482 (4)	0.35252 (8)	0.57538 (11)	0.0784 (6)
H1A	0.550 (6)	0.4250 (7)	0.5783 (16)	0.118*
H1B	0.401 (5)	0.3840 (10)	0.5656 (17)	0.118*
H2A	−0.106 (5)	0.3658 (11)	0.5693 (15)	0.118*
H2B	0.057 (6)	0.3405 (11)	0.6183 (11)	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (16)	0.0508 (16)	0.0471 (16)	−0.0049 (13)	0.0018 (12)	−0.0030 (12)
C2	0.0456 (17)	0.0524 (17)	0.0471 (16)	−0.0061 (13)	−0.0019 (13)	−0.0028 (12)
C3	0.0450 (16)	0.0453 (16)	0.0429 (15)	−0.0086 (13)	0.0026 (13)	−0.0038 (12)
C4	0.0454 (17)	0.0516 (17)	0.0438 (16)	−0.0035 (14)	0.0050 (13)	0.0007 (13)
C5	0.059 (2)	0.0585 (19)	0.0576 (18)	0.0034 (15)	−0.0012 (15)	0.0016 (14)
C6	0.059 (2)	0.081 (2)	0.065 (2)	0.0065 (17)	−0.0061 (16)	0.0095 (17)
C7	0.065 (2)	0.085 (2)	0.0473 (17)	−0.0089 (19)	−0.0062 (15)	0.0023 (16)
C8	0.059 (2)	0.067 (2)	0.0457 (17)	−0.0034 (16)	−0.0011 (15)	−0.0061 (13)
C9	0.0438 (17)	0.0519 (17)	0.0410 (15)	−0.0071 (13)	0.0035 (13)	−0.0003 (13)
C10	0.0514 (18)	0.0609 (19)	0.0577 (17)	0.0003 (15)	0.0041 (14)	−0.0125 (14)
C11	0.0539 (18)	0.0449 (17)	0.0564 (18)	−0.0010 (14)	0.0019 (14)	−0.0040 (13)
C12	0.094 (3)	0.066 (2)	0.059 (2)	−0.0238 (18)	0.0002 (18)	−0.0039 (15)
C13	0.118 (3)	0.071 (2)	0.063 (2)	−0.028 (2)	0.006 (2)	−0.0001 (17)
C14	0.090 (3)	0.065 (2)	0.078 (2)	−0.0169 (19)	−0.002 (2)	−0.0156 (17)
C15	0.077 (2)	0.060 (2)	0.0617 (19)	−0.0070 (17)	0.0044 (16)	−0.0133 (15)
C16	0.0577 (19)	0.0501 (18)	0.0631 (17)	0.0000 (14)	0.0066 (14)	−0.0025 (13)
C17	0.075 (2)	0.0510 (18)	0.0643 (19)	−0.0027 (15)	0.0140 (16)	−0.0023 (14)
C18	0.0615 (19)	0.0475 (18)	0.0512 (17)	0.0001 (15)	0.0052 (15)	−0.0023 (13)
C19	0.0606 (19)	0.060 (2)	0.0489 (17)	−0.0103 (16)	0.0045 (15)	−0.0031 (14)
C20	0.081 (2)	0.087 (3)	0.060 (2)	−0.020 (2)	0.0124 (17)	−0.0076 (17)
C21	0.091 (3)	0.095 (3)	0.067 (2)	−0.033 (2)	0.0096 (19)	0.009 (2)
C22	0.097 (3)	0.065 (2)	0.091 (3)	−0.021 (2)	0.003 (2)	0.0161 (19)
C23	0.079 (2)	0.059 (2)	0.084 (2)	−0.0044 (18)	0.0083 (19)	0.0077 (17)
C24	0.0586 (19)	0.0515 (19)	0.0561 (18)	−0.0039 (15)	0.0001 (15)	0.0057 (14)
C25	0.064 (2)	0.0611 (19)	0.067 (2)	0.0088 (15)	0.0113 (17)	−0.0009 (15)
C26	0.073 (2)	0.065 (2)	0.068 (2)	−0.0030 (17)	0.0106 (18)	−0.0007 (15)
C27	0.059 (2)	0.0496 (18)	0.0570 (18)	0.0074 (15)	0.0091 (15)	−0.0030 (14)
C28	0.074 (2)	0.074 (2)	0.069 (2)	−0.0097 (17)	0.0095 (18)	0.0034 (17)
C29	0.093 (3)	0.084 (3)	0.077 (3)	−0.008 (2)	0.011 (2)	0.0129 (18)
C30	0.072 (2)	0.073 (2)	0.082 (3)	−0.0046 (18)	0.008 (2)	−0.0100 (19)
N1	0.0694 (17)	0.0542 (16)	0.0560 (15)	−0.0058 (13)	0.0115 (13)	−0.0080 (11)
N2	0.0601 (15)	0.0473 (14)	0.0556 (14)	0.0010 (12)	0.0121 (12)	0.0002 (11)
N3	0.095 (2)	0.0646 (18)	0.0815 (19)	−0.0158 (15)	0.0009 (17)	0.0012 (15)
N4	0.0495 (14)	0.0434 (13)	0.0447 (12)	−0.0027 (11)	0.0016 (11)	−0.0047 (10)
N5	0.0442 (13)	0.0499 (14)	0.0464 (13)	−0.0038 (11)	0.0001 (11)	−0.0055 (10)
N6	0.081 (2)	0.079 (2)	0.0691 (18)	0.0029 (16)	0.0082 (15)	0.0018 (15)
O1W	0.0648 (14)	0.0652 (14)	0.0756 (14)	0.0039 (11)	0.0054 (12)	−0.0102 (11)
O2W	0.0671 (15)	0.0882 (17)	0.0804 (15)	0.0068 (12)	0.0079 (13)	−0.0006 (12)

Geometric parameters (Å, º) top

C1—C1ⁱ	1.504 (4)	C16—H16A	0.9700
C1—C2	1.520 (3)	C16—H16B	0.9700
C1—H1	0.9700	C17—C18	1.491 (3)
C1—H2	0.9700	C17—H17A	0.9700
C2—C3	1.491 (3)	C17—H17B	0.9700
C2—H3	0.9700	C18—N1	1.312 (3)
C2—H4	0.9700	C18—N2	1.369 (3)
C3—N5	1.314 (3)	C19—C20	1.384 (4)
C3—N4	1.375 (3)	C19—C24	1.390 (4)
C4—C5	1.390 (3)	C19—N1	1.391 (3)
C4—N5	1.393 (3)	C20—C21	1.375 (4)
C4—C9	1.394 (3)	C20—H20	0.9300
C5—C6	1.380 (3)	C21—C22	1.390 (4)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.390 (4)	C22—C23	1.368 (4)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.372 (4)	C23—C24	1.386 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.390 (3)	C24—N2	1.394 (3)
C8—H8	0.9300	C25—N2	1.467 (3)
C9—N4	1.382 (3)	C25—C27	1.503 (3)
C10—N4	1.462 (3)	C25—H25A	0.9700
C10—C11	1.516 (3)	C25—H25B	0.9700
C10—H10A	0.9700	C26—C30	1.377 (4)
C10—H10B	0.9700	C26—C27	1.383 (4)
C11—C15	1.372 (3)	C26—H26	0.9300
C11—C12	1.376 (3)	C27—C28	1.367 (3)
C12—C13	1.372 (4)	C28—C29	1.390 (4)
C12—H12	0.9300	C28—H28	0.9300
C13—N3	1.326 (3)	C29—N6	1.324 (4)
C13—H13	0.9300	C29—H29	0.9300
C14—N3	1.332 (3)	C30—N6	1.324 (4)
C14—C15	1.381 (4)	C30—H30	0.9300
C14—H14	0.9300	O1W—H1A	0.855 (16)
C15—H15	0.9300	O1W—H1B	0.830 (17)
C16—C16ⁱⁱ	1.502 (4)	O2W—H2A	0.849 (17)
C16—C17	1.510 (3)	O2W—H2B	0.882 (16)

C1ⁱ—C1—C2	112.0 (2)	C18—C17—C16	114.1 (2)
C1ⁱ—C1—H1	109.2	C18—C17—H17A	108.7
C2—C1—H1	109.2	C16—C17—H17A	108.7
C1ⁱ—C1—H2	109.2	C18—C17—H17B	108.7
C2—C1—H2	109.2	C16—C17—H17B	108.7
H1—C1—H2	107.9	H17A—C17—H17B	107.6
C3—C2—C1	113.7 (2)	N1—C18—N2	113.1 (2)
C3—C2—H3	108.8	N1—C18—C17	125.3 (2)
C1—C2—H3	108.8	N2—C18—C17	121.6 (2)
C3—C2—H4	108.8	C20—C19—C24	119.5 (3)
C1—C2—H4	108.8	C20—C19—N1	130.1 (3)
H3—C2—H4	107.7	C24—C19—N1	110.4 (2)
N5—C3—N4	112.3 (2)	C21—C20—C19	118.3 (3)
N5—C3—C2	125.5 (2)	C21—C20—H20	120.8
N4—C3—C2	122.2 (2)	C19—C20—H20	120.8
C5—C4—N5	129.8 (2)	C20—C21—C22	121.1 (3)
C5—C4—C9	120.1 (2)	C20—C21—H21	119.4
N5—C4—C9	110.1 (2)	C22—C21—H21	119.4
C6—C5—C4	117.6 (3)	C23—C22—C21	121.7 (3)
C6—C5—H5	121.2	C23—C22—H22	119.1
C4—C5—H5	121.2	C21—C22—H22	119.1
C5—C6—C7	121.2 (3)	C22—C23—C24	116.6 (3)
C5—C6—H6	119.4	C22—C23—H23	121.7
C7—C6—H6	119.4	C24—C23—H23	121.7
C8—C7—C6	122.4 (3)	C23—C24—C19	122.7 (3)
C8—C7—H7	118.8	C23—C24—N2	132.3 (3)
C6—C7—H7	118.8	C19—C24—N2	105.0 (2)
C7—C8—C9	116.1 (3)	N2—C25—C27	113.1 (2)
C7—C8—H8	122.0	N2—C25—H25A	109.0
C9—C8—H8	122.0	C27—C25—H25A	109.0
N4—C9—C8	132.3 (2)	N2—C25—H25B	109.0
N4—C9—C4	105.1 (2)	C27—C25—H25B	109.0
C8—C9—C4	122.6 (2)	H25A—C25—H25B	107.8
N4—C10—C11	111.8 (2)	C30—C26—C27	119.2 (3)
N4—C10—H10A	109.3	C30—C26—H26	120.4
C11—C10—H10A	109.3	C27—C26—H26	120.4
N4—C10—H10B	109.3	C28—C27—C26	117.1 (3)
C11—C10—H10B	109.3	C28—C27—C25	121.2 (3)
H10A—C10—H10B	107.9	C26—C27—C25	121.7 (3)
C15—C11—C12	116.7 (3)	C27—C28—C29	119.5 (3)
C15—C11—C10	122.1 (3)	C27—C28—H28	120.2
C12—C11—C10	121.2 (2)	C29—C28—H28	120.2
C13—C12—C11	120.6 (3)	N6—C29—C28	123.8 (3)
C13—C12—H12	119.7	N6—C29—H29	118.1
C11—C12—H12	119.7	C28—C29—H29	118.1
N3—C13—C12	123.2 (3)	N6—C30—C26	124.4 (3)
N3—C13—H13	118.4	N6—C30—H30	117.8
C12—C13—H13	118.4	C26—C30—H30	117.8
N3—C14—C15	124.1 (3)	C18—N1—C19	104.9 (2)
N3—C14—H14	118.0	C18—N2—C24	106.5 (2)
C15—C14—H14	118.0	C18—N2—C25	127.6 (2)
C11—C15—C14	119.3 (3)	C24—N2—C25	125.9 (2)
C11—C15—H15	120.4	C13—N3—C14	116.2 (3)
C14—C15—H15	120.4	C3—N4—C9	107.2 (2)
C16ⁱⁱ—C16—C17	113.8 (3)	C3—N4—C10	128.0 (2)
C16ⁱⁱ—C16—H16A	108.8	C9—N4—C10	124.5 (2)
C17—C16—H16A	108.8	C3—N5—C4	105.27 (19)
C16ⁱⁱ—C16—H16B	108.8	C29—N6—C30	116.0 (3)
C17—C16—H16B	108.8	H1A—O1W—H1B	110 (2)
H16A—C16—H16B	107.7	H2A—O2W—H2B	107 (2)

C1ⁱ—C1—C2—C3	178.4 (2)	N2—C25—C27—C28	116.8 (3)
C1—C2—C3—N5	−8.1 (3)	N2—C25—C27—C26	−63.9 (3)
C1—C2—C3—N4	171.3 (2)	C26—C27—C28—C29	−0.8 (4)
N5—C4—C5—C6	179.3 (2)	C25—C27—C28—C29	178.5 (3)
C9—C4—C5—C6	−1.3 (4)	C27—C28—C29—N6	−0.1 (5)
C4—C5—C6—C7	0.1 (4)	C27—C26—C30—N6	0.1 (5)
C5—C6—C7—C8	0.6 (4)	N2—C18—N1—C19	1.0 (3)
C6—C7—C8—C9	−0.1 (4)	C17—C18—N1—C19	−176.9 (2)
C7—C8—C9—N4	179.7 (2)	C20—C19—N1—C18	−179.9 (3)
C7—C8—C9—C4	−1.2 (4)	C24—C19—N1—C18	−0.2 (3)
C5—C4—C9—N4	−178.8 (2)	N1—C18—N2—C24	−1.4 (3)
N5—C4—C9—N4	0.8 (3)	C17—C18—N2—C24	176.6 (2)
C5—C4—C9—C8	1.9 (4)	N1—C18—N2—C25	176.8 (2)
N5—C4—C9—C8	−178.5 (2)	C17—C18—N2—C25	−5.2 (4)
N4—C10—C11—C15	115.2 (3)	C23—C24—N2—C18	−178.8 (3)
N4—C10—C11—C12	−63.3 (3)	C19—C24—N2—C18	1.2 (3)
C15—C11—C12—C13	0.9 (4)	C23—C24—N2—C25	3.0 (5)
C10—C11—C12—C13	179.4 (3)	C19—C24—N2—C25	−177.1 (2)
C11—C12—C13—N3	−0.5 (5)	C27—C25—N2—C18	−83.2 (3)
C12—C11—C15—C14	−0.7 (4)	C27—C25—N2—C24	94.7 (3)
C10—C11—C15—C14	−179.2 (3)	C12—C13—N3—C14	−0.1 (5)
N3—C14—C15—C11	0.1 (5)	C15—C14—N3—C13	0.3 (5)
C16ⁱⁱ—C16—C17—C18	177.3 (3)	N5—C3—N4—C9	−0.1 (3)
C16—C17—C18—N1	4.5 (4)	C2—C3—N4—C9	−179.5 (2)
C16—C17—C18—N2	−173.3 (2)	N5—C3—N4—C10	−173.8 (2)
C24—C19—C20—C21	0.8 (4)	C2—C3—N4—C10	6.8 (4)
N1—C19—C20—C21	−179.6 (3)	C8—C9—N4—C3	178.8 (3)
C19—C20—C21—C22	0.5 (5)	C4—C9—N4—C3	−0.4 (2)
C20—C21—C22—C23	−1.7 (5)	C8—C9—N4—C10	−7.2 (4)
C21—C22—C23—C24	1.5 (5)	C4—C9—N4—C10	173.6 (2)
C22—C23—C24—C19	−0.2 (4)	C11—C10—N4—C3	98.6 (3)
C22—C23—C24—N2	179.8 (3)	C11—C10—N4—C9	−74.2 (3)
C20—C19—C24—C23	−0.9 (4)	N4—C3—N5—C4	0.5 (3)
N1—C19—C24—C23	179.4 (2)	C2—C3—N5—C4	179.9 (2)
C20—C19—C24—N2	179.1 (2)	C5—C4—N5—C3	178.7 (2)
N1—C19—C24—N2	−0.6 (3)	C9—C4—N5—C3	−0.8 (3)
C30—C26—C27—C28	0.8 (4)	C28—C29—N6—C30	1.0 (5)
C30—C26—C27—C25	−178.5 (2)	C26—C30—N6—C29	−1.0 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···N5ⁱⁱⁱ	0.86 (2)	2.01 (2)	2.854 (3)	171 (3)
O1W—H1B···O2W	0.83 (2)	1.97 (2)	2.800 (3)	177 (3)
O2W—H2B···N6^iv	0.88 (2)	2.04 (2)	2.858 (3)	154 (3)
O2W—H2A···O1W^v	0.85 (2)	1.93 (2)	2.779 (3)	178 (3)
C13—H13···O2W	0.93	2.53	3.390 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₃₀H₂₈N₆·2H₂O
M_r	508.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	4.9430 (2), 27.969 (5), 19.042 (5)
β (°)	93.295 (5)
V (Å³)	2628.2 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.971, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16155, 6112, 2470
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.137, 1.00
No. of reflections	6112
No. of parameters	355
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···N5ⁱ	0.86 (2)	2.01 (2)	2.854 (3)	171 (3)
O1W—H1B···O2W	0.83 (2)	1.97 (2)	2.800 (3)	177 (3)
O2W—H2B···N6ⁱⁱ	0.88 (2)	2.04 (2)	2.858 (3)	154 (3)
O2W—H2A···O1Wⁱⁱⁱ	0.85 (2)	1.93 (2)	2.779 (3)	178 (3)
C13—H13···O2W	0.93	2.53	3.390 (4)	154.8

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

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