(1R*,2S*)-N,N'-Bis[(E)-1H-pyrrol-2-yl-methyl-idene]cyclo-hexane-1,2-diamine monohydrate.

The title compound, C16H20N4·H2O, was synthesized from cis-1,2-diamino-cyclo-hexane (a racemic mixture of the (1R,2S) and (1S,2R) enanti-omers). The compound crystallized with two mol-ecules (A and B) in the asymmetric unit with a single water solvent mol-ecule per Schiff base mol-ecule. Mol-ecules A and B have similar conformations as illustrated by the least-squares-fit with an r.m.s. deviation of 0.242 Å. The mol-ecules within the asymmetric unit are bridged by hydrogen bonds to the two water mol-ecules, resulting in a heterotetramer. The water mol-ecule acts as both a hydrogen-bond donor and acceptor. The pyrrole-imine units are not co-planar, making an angle of 73.9 (3)° and 76.9 (3)° in mol-ecules A and B, respectively.

Related literature

For a study of the helical structures formed by both the S,S and R,R bis­(pyrrolide-imine) ligands as well as the ZnII, CuII and NiII chelates in the solid state, see: Wang et al. (2007 ▶). For the solid-state synthesis and X-ray structure of the anhydrous trans racemate of the ligand, see: van den Ancker et al. (2006 ▶). For the TiIV chelate of the trans racemic complex, see: Zhang et al. (2008 ▶). For the inter­molecular inter­action-controlled self-assembly and a study of the photophysics of the PtII chelate of the R,R and S,S enanti­omers as well as the trans racemic complex, see: Shan et al. (2008 ▶). For the X-ray structure and applications of the trans racemate of the PdII chelate as a hydrogenation catalyst, see: Bacchi et al. (2003 ▶).

Experimental

Crystal data

C16H20N4·H2O

M = 286.38

Monoclinic,

a = 9.7207 (7) Å

b = 18.4183 (13) Å

c = 18.2460 (12) Å

β = 92.721 (7)°

V = 3263.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.60 × 0.30 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.956, T max = 0.989

23848 measured reflections

6428 independent reflections

3290 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 0.85

6428 reflections

414 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) 1. DOI: 10.1107/S1600536812046193/vm2181sup1.cif

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

C16H20N4·H2O	F(000) = 1232
Mr = 286.38	Dx = 1.166 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3290 reflections
a = 9.7207 (7) Å	θ = 3.0–26.0°
b = 18.4183 (13) Å	µ = 0.08 mm−1
c = 18.2460 (12) Å	T = 296 K
β = 92.721 (7)°	Needle, colourless
V = 3263.1 (4) Å3	0.60 × 0.30 × 0.15 mm
Z = 8

Oxford Diffraction Xcalibur 2 CCD diffractometer	6428 independent reflections
Radiation source: fine-focus sealed tube	3290 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans at fixed θ angles	θmax = 26.1°, θmin = 3.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→12
Tmin = 0.956, Tmax = 0.989	k = −22→22
23848 measured reflections	l = −22→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3
6428 reflections	(Δ/σ)max = 0.001
414 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 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
C1A	0.1913 (3)	−0.02963 (13)	0.54953 (14)	0.0834 (7)
H1A	0.1123	−0.0581	0.5457	0.100*
C1B	0.1477 (4)	−0.14986 (14)	0.40497 (14)	0.0960 (8)
H1B	0.2269	−0.1680	0.4291	0.115*
C2A	0.2955 (3)	−0.03661 (17)	0.60134 (15)	0.1018 (9)
H2A	0.3006	−0.0704	0.6393	0.122*
C2B	0.0173 (4)	−0.17302 (14)	0.41394 (14)	0.0997 (9)
H2B	−0.0088	−0.2100	0.4451	0.120*
C3A	0.3926 (3)	0.01569 (18)	0.58726 (14)	0.1030 (9)
H3A	0.4750	0.0233	0.6141	0.124*
C3B	−0.0705 (3)	−0.13179 (13)	0.36854 (12)	0.0845 (7)
H3B	−0.1659	−0.1360	0.3640	0.101*
C4A	0.3457 (2)	0.05500 (14)	0.52605 (12)	0.0730 (6)
C4B	0.0090 (3)	−0.08341 (11)	0.33145 (11)	0.0615 (6)
C5A	0.4118 (2)	0.11473 (14)	0.49148 (12)	0.0766 (7)
H5A	0.4998	0.1266	0.5098	0.092*
C5B	−0.0379 (2)	−0.03242 (10)	0.27595 (10)	0.0549 (5)
H5B	−0.1323	−0.0307	0.2648	0.066*
C6A	0.4517 (2)	0.21372 (13)	0.41631 (11)	0.0730 (7)
H6A	0.546 (2)	0.2008 (3)	0.4273 (3)	0.088*
C6B	−0.0344 (2)	0.05047 (10)	0.17992 (9)	0.0503 (5)
H6B	−0.1358 (19)	0.04579 (13)	0.18469 (13)	0.060*
C7A	0.4180 (3)	0.28228 (16)	0.45948 (14)	0.1059 (10)
H7A1	0.4237	0.2712	0.5115	0.127*
H7A2	0.4863	0.3192	0.4505	0.127*
C7B	0.0038 (2)	0.01703 (11)	0.10669 (10)	0.0626 (6)
H7B1	−0.0159	−0.0346	0.1073	0.075*
H7B2	−0.0527	0.0387	0.0673	0.075*
C8A	0.2756 (4)	0.31233 (15)	0.43906 (16)	0.1124 (11)
H8A1	0.2608	0.3563	0.4669	0.135*
H8A2	0.2064	0.2772	0.4518	0.135*
C8B	0.1533 (2)	0.02822 (11)	0.09196 (11)	0.0633 (6)
H8B1	0.1725	0.0072	0.0448	0.076*
H8B2	0.2101	0.0034	0.1293	0.076*
C9A	0.2600 (3)	0.32906 (13)	0.35746 (16)	0.0992 (9)
H9A1	0.1664	0.3446	0.3452	0.119*
H9A2	0.3216	0.3683	0.3456	0.119*
C9B	0.1900 (2)	0.10788 (11)	0.09191 (10)	0.0636 (6)
H9B1	0.1415	0.1316	0.0509	0.076*
H9B2	0.2881	0.1132	0.0858	0.076*
C10A	0.2932 (2)	0.26221 (11)	0.31272 (12)	0.0688 (6)
H10C	0.2228	0.2257	0.3191	0.083*
H10D	0.2913	0.2752	0.2612	0.083*
C10B	0.1521 (2)	0.14446 (10)	0.16339 (10)	0.0546 (5)
H10A	0.2116	0.1261	0.2034	0.065*
H10B	0.1675	0.1963	0.1596	0.065*
C11B	0.0035 (2)	0.13095 (10)	0.18041 (10)	0.0504 (5)
H11B	−0.0552 (12)	0.1553 (5)	0.1421 (8)	0.060*
C12A	0.5241 (2)	0.17287 (11)	0.23370 (11)	0.0575 (5)
H12A	0.5608	0.2187	0.2257	0.069*
C12B	−0.0978 (2)	0.22135 (11)	0.25033 (11)	0.0580 (5)
H12B	−0.1286	0.2390	0.2047	0.070*
C13A	0.6098 (2)	0.12312 (12)	0.11422 (11)	0.0651 (6)
H13A	0.6493	0.1647	0.0954	0.078*
C13B	−0.1349 (2)	0.26176 (10)	0.31397 (11)	0.0568 (5)
C14A	0.6021 (2)	0.05552 (14)	0.08030 (13)	0.0747 (7)
H14A	0.6359	0.0437	0.0350	0.090*
C14B	−0.2075 (2)	0.32555 (12)	0.31707 (14)	0.0760 (7)
H14B	−0.2446	0.3514	0.2770	0.091*
C15A	0.5365 (2)	0.01026 (13)	0.12521 (14)	0.0750 (7)
H15A	0.5163	−0.0383	0.1158	0.090*
C15B	−0.2160 (2)	0.34479 (12)	0.39040 (14)	0.0760 (7)
H15B	−0.2592	0.3857	0.4084	0.091*
C16A	0.54886 (19)	0.11759 (11)	0.18053 (10)	0.0542 (5)
C16B	−0.1498 (2)	0.29299 (13)	0.43048 (13)	0.0773 (7)
H16B	−0.1395	0.2920	0.4814	0.093*
C11A	0.4329 (2)	0.23015 (11)	0.33462 (11)	0.0641 (6)
H11A	0.5029	0.2659	0.3225	0.077*
N1A	0.2222 (2)	0.02607 (10)	0.50414 (10)	0.0681 (5)
N1B	−0.1010 (2)	0.24262 (10)	0.38442 (10)	0.0657 (5)
N2A	0.36308 (17)	0.15331 (10)	0.43840 (9)	0.0634 (5)
N2B	−0.02667 (16)	0.16364 (8)	0.25133 (8)	0.0515 (4)
N3A	0.45633 (16)	0.16439 (8)	0.29072 (8)	0.0564 (4)
N3B	0.03694 (15)	0.01051 (8)	0.24065 (8)	0.0490 (4)
N4A	0.50504 (19)	0.04740 (10)	0.18633 (10)	0.0622 (5)
N4B	0.1423 (3)	−0.09489 (11)	0.35398 (10)	0.0752 (6)
O1W	0.31430 (19)	0.01940 (10)	0.29915 (9)	0.0662 (4)
O2W	0.08724 (17)	0.12068 (8)	0.39628 (9)	0.0597 (4)
H01A	0.163 (2)	0.0437 (12)	0.4667 (13)	0.084 (7)*
H01B	−0.045 (2)	0.2011 (13)	0.3941 (12)	0.088 (8)*
H1W	0.344 (3)	0.0587 (18)	0.3136 (18)	0.143 (15)*
H2W	0.227 (3)	0.0243 (14)	0.2780 (15)	0.111 (10)*
H3W	0.067 (3)	0.1230 (13)	0.3531 (15)	0.097 (10)*
H04A	0.452 (2)	0.0314 (10)	0.2203 (11)	0.060 (6)*
H04B	0.213 (3)	−0.0690 (14)	0.3444 (14)	0.093 (9)*
H4W	0.181 (3)	0.1399 (14)	0.4011 (14)	0.116 (10)*

	U11	U22	U33	U12	U13	U23
C1A	0.1007 (19)	0.0744 (16)	0.0764 (17)	0.0119 (14)	0.0177 (16)	0.0254 (14)
C1B	0.135 (3)	0.0733 (17)	0.0773 (18)	0.0007 (17)	−0.0223 (17)	0.0273 (14)
C2A	0.116 (2)	0.119 (2)	0.0715 (19)	0.0344 (19)	0.0133 (18)	0.0394 (16)
C2B	0.159 (3)	0.0757 (18)	0.0619 (17)	−0.0357 (19)	−0.0142 (18)	0.0187 (13)
C3A	0.0846 (18)	0.164 (3)	0.0595 (16)	0.0235 (19)	−0.0083 (14)	0.0293 (17)
C3B	0.115 (2)	0.0806 (17)	0.0571 (14)	−0.0313 (15)	−0.0029 (14)	0.0140 (13)
C4A	0.0652 (14)	0.1068 (19)	0.0467 (13)	0.0077 (14)	−0.0012 (11)	0.0139 (13)
C4B	0.0913 (17)	0.0508 (13)	0.0424 (12)	−0.0126 (11)	0.0028 (12)	−0.0006 (10)
C5A	0.0606 (13)	0.123 (2)	0.0460 (13)	−0.0104 (14)	−0.0041 (11)	−0.0040 (14)
C5B	0.0678 (13)	0.0512 (12)	0.0453 (11)	−0.0057 (10)	−0.0019 (10)	−0.0054 (10)
C6A	0.0754 (14)	0.0983 (18)	0.0458 (12)	−0.0344 (13)	0.0070 (11)	−0.0200 (12)
C6B	0.0536 (11)	0.0563 (13)	0.0399 (11)	0.0028 (9)	−0.0095 (9)	−0.0005 (9)
C7A	0.150 (3)	0.115 (2)	0.0548 (15)	−0.068 (2)	0.0248 (17)	−0.0360 (15)
C7B	0.0786 (15)	0.0648 (14)	0.0428 (12)	−0.0001 (11)	−0.0125 (10)	−0.0110 (10)
C8A	0.161 (3)	0.0830 (19)	0.098 (2)	−0.038 (2)	0.059 (2)	−0.0525 (16)
C8B	0.0810 (15)	0.0716 (15)	0.0368 (11)	0.0136 (11)	−0.0026 (10)	−0.0119 (10)
C9A	0.139 (2)	0.0598 (15)	0.102 (2)	−0.0112 (15)	0.0414 (19)	−0.0284 (14)
C9B	0.0746 (14)	0.0794 (16)	0.0368 (11)	0.0086 (11)	0.0044 (10)	0.0102 (10)
C10A	0.0991 (18)	0.0484 (12)	0.0598 (14)	−0.0084 (12)	0.0138 (12)	−0.0085 (10)
C10B	0.0754 (13)	0.0478 (11)	0.0401 (11)	−0.0042 (10)	−0.0012 (10)	0.0064 (9)
C11B	0.0691 (13)	0.0499 (12)	0.0312 (10)	0.0088 (10)	−0.0072 (9)	0.0047 (8)
C12A	0.0641 (12)	0.0622 (13)	0.0465 (12)	−0.0104 (10)	0.0053 (10)	−0.0036 (10)
C12B	0.0776 (14)	0.0500 (12)	0.0454 (12)	0.0067 (11)	−0.0061 (10)	0.0032 (9)
C13A	0.0718 (14)	0.0757 (15)	0.0491 (12)	−0.0018 (11)	0.0163 (11)	−0.0016 (11)
C13B	0.0666 (13)	0.0474 (12)	0.0562 (13)	0.0080 (10)	0.0004 (10)	−0.0043 (10)
C14A	0.0742 (15)	0.0912 (18)	0.0603 (15)	0.0071 (13)	0.0209 (12)	−0.0173 (13)
C14B	0.0962 (17)	0.0586 (14)	0.0720 (16)	0.0218 (12)	−0.0082 (13)	0.0002 (12)
C15A	0.0776 (15)	0.0657 (15)	0.0831 (17)	0.0064 (12)	0.0172 (13)	−0.0204 (13)
C15B	0.0831 (16)	0.0575 (14)	0.0882 (19)	0.0126 (12)	0.0123 (14)	−0.0159 (13)
C16A	0.0593 (12)	0.0586 (13)	0.0449 (12)	−0.0013 (10)	0.0046 (10)	−0.0016 (10)
C16B	0.0989 (17)	0.0711 (16)	0.0631 (15)	0.0170 (14)	0.0171 (13)	−0.0071 (13)
C11A	0.0831 (15)	0.0620 (13)	0.0484 (12)	−0.0293 (12)	0.0154 (11)	−0.0167 (10)
N1A	0.0729 (13)	0.0778 (13)	0.0533 (11)	0.0068 (11)	0.0006 (10)	0.0151 (10)
N1B	0.0864 (13)	0.0570 (11)	0.0545 (12)	0.0201 (10)	0.0112 (10)	−0.0006 (9)
N2A	0.0669 (11)	0.0879 (13)	0.0353 (9)	−0.0162 (9)	0.0004 (8)	−0.0047 (9)
N2B	0.0695 (10)	0.0470 (9)	0.0377 (9)	0.0084 (8)	−0.0005 (8)	0.0002 (7)
N3A	0.0692 (11)	0.0614 (11)	0.0394 (9)	−0.0114 (8)	0.0113 (8)	−0.0074 (8)
N3B	0.0602 (10)	0.0465 (9)	0.0399 (9)	−0.0024 (8)	−0.0024 (8)	−0.0005 (7)
N4A	0.0702 (11)	0.0622 (12)	0.0555 (11)	0.0013 (9)	0.0150 (10)	−0.0001 (9)
N4B	0.0966 (17)	0.0629 (13)	0.0653 (13)	−0.0041 (12)	−0.0064 (12)	0.0177 (10)
O1W	0.0643 (10)	0.0714 (12)	0.0625 (10)	−0.0013 (9)	−0.0032 (8)	0.0150 (8)
O2W	0.0682 (10)	0.0679 (10)	0.0427 (9)	0.0000 (7)	−0.0019 (8)	0.0094 (7)

C1A—C2A	1.358 (3)	C9A—H9A2	0.9700
C1A—N1A	1.361 (3)	C9B—C10B	1.528 (3)
C1A—H1A	0.9300	C9B—H9B1	0.9700
C1B—C2B	1.355 (4)	C9B—H9B2	0.9700
C1B—N4B	1.374 (3)	C10A—C11A	1.517 (3)
C1B—H1B	0.9300	C10A—H10C	0.9700
C2A—C3A	1.381 (4)	C10A—H10D	0.9700
C2A—H2A	0.9300	C10B—C11B	1.512 (3)
C2B—C3B	1.387 (3)	C10B—H10A	0.9700
C2B—H2B	0.9300	C10B—H10B	0.9700
C3A—C4A	1.390 (3)	C11B—N2B	1.469 (2)
C3A—H3A	0.9300	C11B—H11B	0.9894
C3B—C4B	1.378 (3)	C12A—N3A	1.267 (2)
C3B—H3B	0.9300	C12A—C16A	1.435 (3)
C4A—N1A	1.356 (3)	C12A—H12A	0.9300
C4A—C5A	1.435 (3)	C12B—N2B	1.268 (2)
C4B—N4B	1.357 (3)	C12B—C13B	1.439 (3)
C4B—C5B	1.439 (3)	C12B—H12B	0.9300
C5A—N2A	1.274 (3)	C13A—C16A	1.376 (3)
C5A—H5A	0.9300	C13A—C14A	1.391 (3)
C5B—N3B	1.271 (2)	C13A—H13A	0.9300
C5B—H5B	0.9300	C13B—N1B	1.358 (2)
C6A—N2A	1.475 (3)	C13B—C14B	1.373 (3)
C6A—C11A	1.523 (3)	C14A—C15A	1.350 (3)
C6A—C7A	1.532 (3)	C14A—H14A	0.9300
C6A—H6A	0.9609	C14B—C15B	1.390 (3)
C6B—N3B	1.476 (2)	C14B—H14B	0.9300
C6B—C11B	1.527 (3)	C15A—N4A	1.356 (3)
C6B—C7B	1.533 (3)	C15A—H15A	0.9300
C6B—H6B	0.9975	C15B—C16B	1.347 (3)
C7A—C8A	1.520 (4)	C15B—H15B	0.9300
C7A—H7A1	0.9700	C16A—N4A	1.367 (3)
C7A—H7A2	0.9700	C16B—N1B	1.353 (3)
C7B—C8B	1.505 (3)	C16B—H16B	0.9300
C7B—H7B1	0.9700	C11A—N3A	1.476 (2)
C7B—H7B2	0.9700	C11A—H11A	0.9800
C8A—C9A	1.521 (4)	N1A—H01A	0.93 (2)
C8A—H8A1	0.9700	N1B—H01B	0.95 (2)
C8A—H8A2	0.9700	N4A—H04A	0.88 (2)
C8B—C9B	1.510 (3)	N4B—H04B	0.86 (2)
C8B—H8B1	0.9700	O1W—H1W	0.82 (3)
C8B—H8B2	0.9700	O1W—H2W	0.92 (3)
C9A—C10A	1.520 (3)	O2W—H3W	0.81 (3)
C9A—H9A1	0.9700	O2W—H4W	0.98 (3)
C2A—C1A—N1A	108.4 (3)	C8B—C9B—H9B2	109.4
C2A—C1A—H1A	125.8	C10B—C9B—H9B2	109.4
N1A—C1A—H1A	125.8	H9B1—C9B—H9B2	108.0
C2B—C1B—N4B	107.9 (3)	C11A—C10A—C9A	112.6 (2)
C2B—C1B—H1B	126.0	C11A—C10A—H10C	109.1
N4B—C1B—H1B	126.0	C9A—C10A—H10C	109.1
C1A—C2A—C3A	107.3 (2)	C11A—C10A—H10D	109.1
C1A—C2A—H2A	126.3	C9A—C10A—H10D	109.1
C3A—C2A—H2A	126.3	H10C—C10A—H10D	107.8
C1B—C2B—C3B	107.9 (2)	C11B—C10B—C9B	111.97 (16)
C1B—C2B—H2B	126.0	C11B—C10B—H10A	109.2
C3B—C2B—H2B	126.0	C9B—C10B—H10A	109.2
C2A—C3A—C4A	108.2 (2)	C11B—C10B—H10B	109.2
C2A—C3A—H3A	125.9	C9B—C10B—H10B	109.2
C4A—C3A—H3A	125.9	H10A—C10B—H10B	107.9
C4B—C3B—C2B	107.7 (2)	N2B—C11B—C10B	110.24 (15)
C4B—C3B—H3B	126.2	N2B—C11B—C6B	110.17 (14)
C2B—C3B—H3B	126.2	C10B—C11B—C6B	113.02 (15)
N1A—C4A—C3A	106.5 (2)	N2B—C11B—H11B	107.7
N1A—C4A—C5A	125.5 (2)	C10B—C11B—H11B	107.7
C3A—C4A—C5A	128.0 (3)	C6B—C11B—H11B	107.7
N4B—C4B—C3B	107.5 (2)	N3A—C12A—C16A	125.31 (19)
N4B—C4B—C5B	125.49 (19)	N3A—C12A—H12A	117.3
C3B—C4B—C5B	127.0 (2)	C16A—C12A—H12A	117.3
N2A—C5A—C4A	127.1 (2)	N2B—C12B—C13B	125.39 (18)
N2A—C5A—H5A	116.4	N2B—C12B—H12B	117.3
C4A—C5A—H5A	116.4	C13B—C12B—H12B	117.3
N3B—C5B—C4B	126.36 (19)	C16A—C13A—C14A	108.0 (2)
N3B—C5B—H5B	116.8	C16A—C13A—H13A	126.0
C4B—C5B—H5B	116.8	C14A—C13A—H13A	126.0
N2A—C6A—C11A	111.87 (16)	N1B—C13B—C14B	106.57 (18)
N2A—C6A—C7A	109.82 (18)	N1B—C13B—C12B	124.79 (18)
C11A—C6A—C7A	108.7 (2)	C14B—C13B—C12B	128.6 (2)
N2A—C6A—H6A	108.8	C15A—C14A—C13A	107.43 (19)
C11A—C6A—H6A	108.8	C15A—C14A—H14A	126.3
C7A—C6A—H6A	108.8	C13A—C14A—H14A	126.3
N3B—C6B—C11B	112.01 (14)	C13B—C14B—C15B	108.2 (2)
N3B—C6B—C7B	109.23 (15)	C13B—C14B—H14B	125.9
C11B—C6B—C7B	109.08 (15)	C15B—C14B—H14B	125.9
N3B—C6B—H6B	108.8	C14A—C15A—N4A	108.6 (2)
C11B—C6B—H6B	108.8	C14A—C15A—H15A	125.7
C7B—C6B—H6B	108.8	N4A—C15A—H15A	125.7
C8A—C7A—C6A	112.9 (2)	C16B—C15B—C14B	107.0 (2)
C8A—C7A—H7A1	109.0	C16B—C15B—H15B	126.5
C6A—C7A—H7A1	109.0	C14B—C15B—H15B	126.5
C8A—C7A—H7A2	109.0	N4A—C16A—C13A	106.68 (18)
C6A—C7A—H7A2	109.0	N4A—C16A—C12A	123.78 (18)
H7A1—C7A—H7A2	107.8	C13A—C16A—C12A	129.4 (2)
C8B—C7B—C6B	112.12 (16)	C15B—C16B—N1B	108.7 (2)
C8B—C7B—H7B1	109.2	C15B—C16B—H16B	125.6
C6B—C7B—H7B1	109.2	N1B—C16B—H16B	125.6
C8B—C7B—H7B2	109.2	N3A—C11A—C10A	109.62 (16)
C6B—C7B—H7B2	109.2	N3A—C11A—C6A	110.71 (18)
H7B1—C7B—H7B2	107.9	C10A—C11A—C6A	113.55 (18)
C7A—C8A—C9A	111.2 (2)	N3A—C11A—H11A	107.6
C7A—C8A—H8A1	109.4	C10A—C11A—H11A	107.6
C9A—C8A—H8A1	109.4	C6A—C11A—H11A	107.6
C7A—C8A—H8A2	109.4	C4A—N1A—C1A	109.6 (2)
C9A—C8A—H8A2	109.4	C4A—N1A—H01A	126.1 (14)
H8A1—C8A—H8A2	108.0	C1A—N1A—H01A	124.1 (14)
C7B—C8B—C9B	111.30 (17)	C16B—N1B—C13B	109.48 (19)
C7B—C8B—H8B1	109.4	C16B—N1B—H01B	130.6 (14)
C9B—C8B—H8B1	109.4	C13B—N1B—H01B	119.7 (14)
C7B—C8B—H8B2	109.4	C5A—N2A—C6A	115.31 (19)
C9B—C8B—H8B2	109.4	C12B—N2B—C11B	117.55 (15)
H8B1—C8B—H8B2	108.0	C12A—N3A—C11A	116.37 (16)
C10A—C9A—C8A	110.3 (2)	C5B—N3B—C6B	115.52 (16)
C10A—C9A—H9A1	109.6	C15A—N4A—C16A	109.28 (19)
C8A—C9A—H9A1	109.6	C15A—N4A—H04A	125.2 (13)
C10A—C9A—H9A2	109.6	C16A—N4A—H04A	124.7 (13)
C8A—C9A—H9A2	109.6	C4B—N4B—C1B	109.0 (2)
H9A1—C9A—H9A2	108.1	C4B—N4B—H04B	127.7 (17)
C8B—C9B—C10B	111.18 (15)	C1B—N4B—H04B	122.7 (18)
C8B—C9B—H9B1	109.4	H1W—O1W—H2W	110 (3)
C10B—C9B—H9B1	109.4	H3W—O2W—H4W	105 (2)
N1A—C1A—C2A—C3A	−0.2 (3)	C14A—C13A—C16A—N4A	0.0 (2)
N4B—C1B—C2B—C3B	−0.4 (3)	C14A—C13A—C16A—C12A	−176.2 (2)
C1A—C2A—C3A—C4A	0.2 (3)	N3A—C12A—C16A—N4A	−2.1 (3)
C1B—C2B—C3B—C4B	0.3 (3)	N3A—C12A—C16A—C13A	173.5 (2)
C2A—C3A—C4A—N1A	−0.1 (3)	C14B—C15B—C16B—N1B	0.0 (3)
C2A—C3A—C4A—C5A	179.8 (2)	C9A—C10A—C11A—N3A	178.26 (18)
C2B—C3B—C4B—N4B	−0.1 (3)	C9A—C10A—C11A—C6A	53.9 (2)
C2B—C3B—C4B—C5B	176.8 (2)	N2A—C6A—C11A—N3A	−55.2 (2)
N1A—C4A—C5A—N2A	5.0 (4)	C7A—C6A—C11A—N3A	−176.66 (18)
C3A—C4A—C5A—N2A	−174.8 (3)	N2A—C6A—C11A—C10A	68.6 (2)
N4B—C4B—C5B—N3B	−1.5 (3)	C7A—C6A—C11A—C10A	−52.9 (2)
C3B—C4B—C5B—N3B	−177.9 (2)	C3A—C4A—N1A—C1A	0.0 (3)
N2A—C6A—C7A—C8A	−67.8 (3)	C5A—C4A—N1A—C1A	−179.9 (2)
C11A—C6A—C7A—C8A	54.9 (3)	C2A—C1A—N1A—C4A	0.2 (3)
N3B—C6B—C7B—C8B	−66.8 (2)	C15B—C16B—N1B—C13B	0.3 (3)
C11B—C6B—C7B—C8B	56.0 (2)	C14B—C13B—N1B—C16B	−0.4 (2)
C6A—C7A—C8A—C9A	−57.4 (3)	C12B—C13B—N1B—C16B	179.0 (2)
C6B—C7B—C8B—C9B	−57.8 (2)	C4A—C5A—N2A—C6A	177.1 (2)
C7A—C8A—C9A—C10A	54.9 (3)	C11A—C6A—N2A—C5A	148.9 (2)
C7B—C8B—C9B—C10B	55.1 (2)	C7A—C6A—N2A—C5A	−90.3 (3)
C8A—C9A—C10A—C11A	−53.4 (3)	C13B—C12B—N2B—C11B	−178.54 (18)
C8B—C9B—C10B—C11B	−52.8 (2)	C10B—C11B—N2B—C12B	105.68 (19)
C9B—C10B—C11B—N2B	176.98 (15)	C6B—C11B—N2B—C12B	−128.92 (18)
C9B—C10B—C11B—C6B	53.2 (2)	C16A—C12A—N3A—C11A	−174.75 (18)
N3B—C6B—C11B—N2B	−56.5 (2)	C10A—C11A—N3A—C12A	95.5 (2)
C7B—C6B—C11B—N2B	−177.59 (15)	C6A—C11A—N3A—C12A	−138.48 (19)
N3B—C6B—C11B—C10B	67.27 (19)	C4B—C5B—N3B—C6B	172.32 (17)
C7B—C6B—C11B—C10B	−53.8 (2)	C11B—C6B—N3B—C5B	134.21 (17)
N2B—C12B—C13B—N1B	−1.5 (3)	C7B—C6B—N3B—C5B	−104.84 (19)
N2B—C12B—C13B—C14B	177.8 (2)	C14A—C15A—N4A—C16A	0.9 (3)
C16A—C13A—C14A—C15A	0.5 (3)	C13A—C16A—N4A—C15A	−0.5 (2)
N1B—C13B—C14B—C15B	0.4 (3)	C12A—C16A—N4A—C15A	175.93 (18)
C12B—C13B—C14B—C15B	−179.0 (2)	C3B—C4B—N4B—C1B	−0.1 (3)
C13A—C14A—C15A—N4A	−0.8 (3)	C5B—C4B—N4B—C1B	−177.1 (2)
C13B—C14B—C15B—C16B	−0.3 (3)	C2B—C1B—N4B—C4B	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N3A	0.82 (3)	2.28 (3)	3.014 (2)	149 (3)
O1W—H2W···N3B	0.92 (3)	1.96 (3)	2.857 (2)	166 (3)
O2W—H3W···N2B	0.80 (3)	2.16 (3)	2.927 (2)	159 (3)
O2W—H4W···N2A	0.98 (3)	1.88 (3)	2.819 (2)	159 (2)
N1A—H01A···O2W	0.93 (2)	2.03 (2)	2.896 (2)	154 (2)
N1B—H01B···O2W	0.95 (2)	1.96 (2)	2.899 (2)	169 (2)
N4A—H04A···O1W	0.88 (2)	2.02 (2)	2.882 (3)	166 (2)
N4B—H04B···O1W	0.86 (3)	2.09 (3)	2.896 (3)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N3A	0.82 (3)	2.28 (3)	3.014 (2)	149 (3)
O1W—H2W⋯N3B	0.92 (3)	1.96 (3)	2.857 (2)	166 (3)
O2W—H3W⋯N2B	0.80 (3)	2.16 (3)	2.927 (2)	159 (3)
O2W—H4W⋯N2A	0.98 (3)	1.88 (3)	2.819 (2)	159 (2)
N1A—H01A⋯O2W	0.93 (2)	2.03 (2)	2.896 (2)	154 (2)
N1B—H01B⋯O2W	0.95 (2)	1.96 (2)	2.899 (2)	169 (2)
N4A—H04A⋯O1W	0.88 (2)	2.02 (2)	2.882 (3)	166 (2)
N4B—H04B⋯O1W	0.86 (3)	2.09 (3)	2.896 (3)	155 (2)