6-Amino-2,5-bis-(pivaloylamino)pyrimidin-4(3H)-one dihydrate.

The asymmetric unit of the title compound, C(14)H(23)N(5)O(3)·2H(2)O, contains two crystallographically independent 6-amino-2,5-bis-(pivaloylamino)pyrimidin-4(3H)-one mol-ecules (A and B) with similar geometry and four water mol-ecules. In both independent mol-ecules, one of the amide groups is almost coplanar with the pyrimidine ring [dihedral angle of 12.85 (9) in A and 12.30 (10)° in B], whereas the other amide group is significantly twisted away from it [dihedral angle is 72.18 (7) in A and 71.29 (7)° in B]. In each independent mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. Mol-ecules A and B are linked into chains along the a axis by N-H⋯O and C-H⋯O hydrogen bonds. Adjacent chains are linked into a two-dimensional network parallel to the ac plane by water mol-ecules via N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For general background on substituted pyrimidines, see: Lednicer & Mitscher (1977 ▶); Blackburn & Gait (1996 ▶); VanAllan (1976 ▶); Goswami et al. (2007 ▶); Brown (1988 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H23N5O3·2H2O

M = 345.41

Triclinic,

a = 7.5560 (3) Å

b = 14.1008 (6) Å

c = 18.0713 (6) Å

α = 71.079 (2)°

β = 89.988 (2)°

γ = 86.682 (3)°

V = 1817.98 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.57 × 0.19 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.947, T max = 0.991

10525 measured reflections

10525 independent reflections

8199 reflections with I > 2σ(I)

R int = 0.0000

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.162

S = 1.11

10525 reflections

447 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019461/ci2809sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019461/ci2809Isup2.hkl

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

C14H23N5O3·2H2O	Z = 4
Mr = 345.41	F(000) = 744
Triclinic, P1	Dx = 1.262 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5560 (3) Å	Cell parameters from 8925 reflections
b = 14.1008 (6) Å	θ = 3.1–32.5°
c = 18.0713 (6) Å	µ = 0.10 mm−1
α = 71.079 (2)°	T = 100 K
β = 89.988 (2)°	Block, colourless
γ = 86.682 (3)°	0.57 × 0.19 × 0.09 mm
V = 1817.98 (12) Å3

Bruker SMART APEXII CCD area-detector diffractometer	10525 independent reflections
Radiation source: fine-focus sealed tube	8199 reflections with I > 2σ(I)
graphite	Rint = 0.0000
φ and ω scans	θmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.947, Tmax = 0.991	k = −18→19
10525 measured reflections	l = 0→25

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0332P)2 + 1.7967P] where P = (Fo2 + 2Fc2)/3
10525 reflections	(Δ/σ)max = 0.001
447 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A	1.0113 (2)	0.26217 (11)	0.14678 (9)	0.0172 (3)
O2A	0.9781 (2)	−0.00932 (11)	0.11107 (8)	0.0163 (3)
O3A	1.2104 (2)	−0.26095 (12)	0.29920 (9)	0.0211 (3)
N1A	0.7981 (2)	0.15883 (12)	0.14173 (9)	0.0126 (3)
H1AA	0.6995	0.1522	0.1207	0.015*
N2A	0.9705 (2)	−0.00908 (12)	0.33668 (9)	0.0124 (3)
N3A	1.0445 (2)	−0.08254 (12)	0.24031 (9)	0.0126 (3)
H3AA	1.0950	−0.1334	0.2306	0.015*
N4A	1.1220 (2)	−0.16358 (12)	0.37291 (9)	0.0129 (3)
H4AA	1.1299	−0.1587	0.4190	0.016*
N5A	0.8070 (2)	0.14048 (13)	0.30396 (10)	0.0151 (3)
H5AA	0.8136	0.1356	0.3526	0.018*
H5AB	0.7506	0.1916	0.2712	0.018*
C1A	0.8701 (3)	0.24963 (15)	0.11802 (11)	0.0121 (4)
C2A	0.8808 (3)	0.07412 (14)	0.20033 (11)	0.0121 (4)
C3A	0.8843 (3)	0.06879 (14)	0.27938 (11)	0.0120 (4)
C4A	1.0438 (3)	−0.08141 (14)	0.31492 (11)	0.0126 (4)
C5A	0.9655 (3)	−0.00353 (15)	0.17828 (11)	0.0120 (4)
C6A	1.1882 (3)	−0.25228 (15)	0.36395 (11)	0.0137 (4)
C7A	1.2277 (3)	−0.33855 (15)	0.44031 (12)	0.0154 (4)
C8A	1.2899 (3)	−0.43211 (17)	0.42020 (13)	0.0211 (5)
H8AA	1.1995	−0.4482	0.3896	0.032*
H8AB	1.3124	−0.4874	0.4676	0.032*
H8AC	1.3967	−0.4196	0.3907	0.032*
C9A	1.3758 (4)	−0.31103 (18)	0.48672 (14)	0.0228 (5)
H9AA	1.3385	−0.2512	0.4983	0.034*
H9AB	1.4811	−0.2995	0.4561	0.034*
H9AC	1.4001	−0.3652	0.5347	0.034*
C10A	1.0576 (3)	−0.35827 (17)	0.48821 (13)	0.0217 (5)
H10A	0.9629	−0.3673	0.4562	0.033*
H10B	1.0265	−0.3021	0.5056	0.033*
H10C	1.0771	−0.4178	0.5328	0.033*
C11A	0.7768 (3)	0.33580 (15)	0.05214 (12)	0.0152 (4)
C12A	0.9017 (4)	0.3536 (2)	−0.01777 (14)	0.0334 (6)
H12A	0.8555	0.4103	−0.0604	0.050*
H12B	0.9102	0.2951	−0.0340	0.050*
H12C	1.0172	0.3666	−0.0026	0.050*
C13A	0.7607 (4)	0.42818 (17)	0.07890 (17)	0.0278 (5)
H13A	0.6818	0.4161	0.1222	0.042*
H13B	0.7147	0.4852	0.0365	0.042*
H13C	0.8754	0.4413	0.0948	0.042*
C14A	0.5943 (3)	0.31374 (17)	0.02795 (14)	0.0226 (5)
H14A	0.5179	0.2988	0.0722	0.034*
H14B	0.6054	0.2572	0.0093	0.034*
H14C	0.5447	0.3714	−0.0129	0.034*
O1B	0.5105 (2)	0.26137 (11)	0.21892 (9)	0.0177 (3)
O2B	0.4795 (2)	−0.01130 (11)	0.39406 (8)	0.0160 (3)
O3B	0.7098 (2)	−0.26303 (12)	0.33417 (9)	0.0213 (3)
N1B	0.3005 (2)	0.15684 (12)	0.27823 (10)	0.0124 (3)
H1BA	0.2027	0.1501	0.3032	0.015*
N2B	0.4710 (2)	−0.01103 (12)	0.16825 (9)	0.0124 (3)
N3B	0.5460 (2)	−0.08400 (12)	0.30196 (9)	0.0125 (3)
H3BA	0.5972	−0.1345	0.3374	0.015*
N4B	0.6226 (2)	−0.16539 (13)	0.21065 (10)	0.0135 (3)
H4BA	0.6310	−0.1607	0.1622	0.016*
N5B	0.3072 (2)	0.13860 (13)	0.12500 (10)	0.0143 (3)
H5BA	0.3129	0.1333	0.0790	0.017*
H5BB	0.2512	0.1899	0.1319	0.017*
C1B	0.3719 (3)	0.24772 (15)	0.25544 (11)	0.0123 (4)
C2B	0.3819 (3)	0.07227 (14)	0.26221 (11)	0.0124 (4)
C3B	0.3855 (3)	0.06723 (14)	0.18588 (11)	0.0113 (3)
C4B	0.5443 (3)	−0.08344 (14)	0.22681 (11)	0.0118 (4)
C5B	0.4673 (3)	−0.00523 (15)	0.32382 (11)	0.0129 (4)
C6B	0.6886 (3)	−0.25413 (15)	0.26499 (12)	0.0149 (4)
C7B	0.7303 (3)	−0.34013 (16)	0.23251 (12)	0.0162 (4)
C8B	0.7917 (4)	−0.43431 (17)	0.30020 (14)	0.0226 (5)
H8BA	0.7000	−0.4511	0.3382	0.034*
H8BB	0.8970	−0.4216	0.3242	0.034*
H8BC	0.8165	−0.4892	0.2805	0.034*
C9B	0.8798 (4)	−0.31215 (18)	0.17286 (14)	0.0232 (5)
H9BA	0.8418	−0.2534	0.1302	0.035*
H9BB	0.9078	−0.3669	0.1534	0.035*
H9BC	0.9832	−0.2987	0.1978	0.035*
C10B	0.5631 (3)	−0.36058 (17)	0.19338 (14)	0.0231 (5)
H10D	0.5312	−0.3038	0.1481	0.035*
H10E	0.4676	−0.3716	0.2297	0.035*
H10F	0.5858	−0.4191	0.1779	0.035*
C11B	0.2801 (3)	0.33333 (16)	0.27831 (12)	0.0150 (4)
C12B	0.4114 (4)	0.3547 (2)	0.33506 (17)	0.0323 (6)
H12D	0.4266	0.2970	0.3813	0.049*
H12E	0.3659	0.4114	0.3491	0.049*
H12F	0.5235	0.3691	0.3102	0.049*
C13B	0.2533 (3)	0.42518 (17)	0.20411 (14)	0.0214 (5)
H13D	0.1719	0.4108	0.1689	0.032*
H13E	0.3650	0.4404	0.1791	0.032*
H13F	0.2062	0.4817	0.2180	0.032*
C14B	0.1021 (4)	0.30911 (17)	0.31798 (15)	0.0236 (5)
H14D	0.0220	0.2929	0.2833	0.035*
H14E	0.0533	0.3663	0.3305	0.035*
H14F	0.1191	0.2529	0.3651	0.035*
O1W	0.8987 (2)	0.12286 (11)	0.47888 (8)	0.0179 (3)
H1W1	0.8648	0.0614	0.4942	0.027*
H2W1	1.0149	0.1036	0.4798	0.027*
O2W	0.2630 (2)	0.06473 (13)	0.48386 (9)	0.0219 (3)
H1W2	0.3371	0.0602	0.4483	0.033*
H2W2	0.3376	0.0610	0.5230	0.033*
O3W	0.2385 (2)	0.93480 (13)	0.01760 (9)	0.0225 (3)
H1W3	0.1642	0.9417	−0.0197	0.034*
H2W3	0.1705	0.9430	0.0559	0.034*
O4W	0.6016 (2)	0.87651 (11)	0.04160 (9)	0.0181 (3)
H1W4	0.6432	0.9365	0.0213	0.027*
H2W4	0.4873	0.8911	0.0321	0.027*

	U11	U22	U33	U12	U13	U23
O1A	0.0161 (7)	0.0141 (7)	0.0198 (7)	−0.0005 (6)	−0.0036 (6)	−0.0033 (6)
O2A	0.0219 (8)	0.0187 (7)	0.0083 (6)	0.0010 (6)	−0.0016 (5)	−0.0050 (5)
O3A	0.0304 (9)	0.0205 (8)	0.0122 (7)	0.0059 (7)	−0.0003 (6)	−0.0064 (6)
N1A	0.0131 (8)	0.0133 (8)	0.0096 (7)	−0.0008 (6)	−0.0027 (6)	−0.0013 (6)
N2A	0.0155 (8)	0.0121 (8)	0.0091 (7)	0.0010 (6)	−0.0006 (6)	−0.0032 (6)
N3A	0.0166 (9)	0.0113 (7)	0.0098 (7)	0.0017 (6)	0.0001 (6)	−0.0038 (6)
N4A	0.0181 (9)	0.0128 (8)	0.0076 (7)	0.0011 (6)	−0.0022 (6)	−0.0034 (6)
N5A	0.0211 (9)	0.0140 (8)	0.0099 (7)	0.0028 (7)	−0.0001 (6)	−0.0039 (6)
C1A	0.0135 (9)	0.0124 (9)	0.0104 (8)	0.0001 (7)	0.0030 (7)	−0.0039 (7)
C2A	0.0139 (9)	0.0117 (8)	0.0093 (8)	−0.0004 (7)	−0.0003 (7)	−0.0016 (6)
C3A	0.0122 (9)	0.0121 (8)	0.0115 (8)	−0.0020 (7)	0.0008 (7)	−0.0034 (7)
C4A	0.0144 (9)	0.0121 (9)	0.0101 (8)	−0.0021 (7)	−0.0001 (7)	−0.0018 (7)
C5A	0.0130 (9)	0.0123 (9)	0.0100 (8)	−0.0011 (7)	−0.0006 (7)	−0.0025 (7)
C6A	0.0161 (10)	0.0127 (9)	0.0117 (8)	0.0008 (7)	−0.0024 (7)	−0.0036 (7)
C7A	0.0212 (11)	0.0116 (9)	0.0123 (8)	0.0031 (8)	−0.0009 (7)	−0.0028 (7)
C8A	0.0267 (12)	0.0162 (10)	0.0195 (10)	0.0064 (9)	−0.0036 (9)	−0.0060 (8)
C9A	0.0289 (13)	0.0181 (10)	0.0203 (10)	0.0041 (9)	−0.0108 (9)	−0.0058 (8)
C10A	0.0285 (12)	0.0152 (10)	0.0176 (10)	0.0022 (9)	0.0055 (9)	−0.0008 (8)
C11A	0.0162 (10)	0.0114 (9)	0.0134 (9)	0.0014 (7)	0.0011 (7)	0.0020 (7)
C12A	0.0294 (14)	0.0379 (14)	0.0190 (11)	0.0033 (11)	0.0085 (10)	0.0091 (10)
C13A	0.0262 (13)	0.0136 (10)	0.0416 (14)	0.0029 (9)	−0.0079 (11)	−0.0068 (10)
C14A	0.0252 (12)	0.0180 (10)	0.0197 (10)	0.0009 (9)	−0.0074 (9)	0.0003 (8)
O1B	0.0167 (8)	0.0150 (7)	0.0211 (7)	−0.0010 (6)	0.0034 (6)	−0.0054 (6)
O2B	0.0196 (8)	0.0199 (7)	0.0100 (6)	0.0030 (6)	−0.0009 (5)	−0.0078 (5)
O3B	0.0317 (9)	0.0179 (7)	0.0140 (7)	0.0072 (6)	−0.0030 (6)	−0.0061 (6)
N1B	0.0126 (8)	0.0126 (8)	0.0144 (7)	0.0003 (6)	0.0023 (6)	−0.0077 (6)
N2B	0.0147 (8)	0.0128 (8)	0.0109 (7)	0.0001 (6)	0.0002 (6)	−0.0057 (6)
N3B	0.0163 (9)	0.0116 (7)	0.0096 (7)	0.0020 (6)	−0.0005 (6)	−0.0039 (6)
N4B	0.0189 (9)	0.0134 (8)	0.0099 (7)	0.0019 (7)	0.0003 (6)	−0.0065 (6)
N5B	0.0188 (9)	0.0136 (8)	0.0112 (7)	0.0028 (6)	−0.0018 (6)	−0.0055 (6)
C1B	0.0147 (10)	0.0115 (9)	0.0109 (8)	0.0016 (7)	−0.0033 (7)	−0.0045 (7)
C2B	0.0141 (9)	0.0123 (9)	0.0131 (8)	−0.0008 (7)	0.0005 (7)	−0.0075 (7)
C3B	0.0111 (9)	0.0118 (8)	0.0115 (8)	−0.0015 (7)	−0.0005 (7)	−0.0046 (7)
C4B	0.0120 (9)	0.0120 (8)	0.0128 (8)	−0.0008 (7)	0.0012 (7)	−0.0060 (7)
C5B	0.0136 (9)	0.0144 (9)	0.0128 (8)	−0.0017 (7)	0.0026 (7)	−0.0072 (7)
C6B	0.0149 (10)	0.0137 (9)	0.0167 (9)	0.0006 (7)	0.0012 (7)	−0.0061 (7)
C7B	0.0213 (11)	0.0139 (9)	0.0151 (9)	0.0025 (8)	−0.0003 (8)	−0.0077 (7)
C8B	0.0314 (13)	0.0146 (10)	0.0207 (10)	0.0058 (9)	−0.0015 (9)	−0.0052 (8)
C9B	0.0279 (13)	0.0197 (11)	0.0213 (10)	0.0055 (9)	0.0072 (9)	−0.0070 (8)
C10B	0.0278 (13)	0.0183 (10)	0.0254 (11)	0.0016 (9)	−0.0080 (9)	−0.0104 (9)
C11B	0.0182 (10)	0.0127 (9)	0.0156 (9)	0.0024 (8)	−0.0023 (8)	−0.0072 (7)
C12B	0.0392 (16)	0.0310 (13)	0.0356 (14)	0.0070 (11)	−0.0154 (12)	−0.0244 (11)
C13B	0.0234 (12)	0.0134 (10)	0.0259 (11)	0.0010 (8)	0.0008 (9)	−0.0048 (8)
C14B	0.0283 (13)	0.0164 (10)	0.0272 (11)	0.0030 (9)	0.0100 (10)	−0.0092 (9)
O1W	0.0225 (8)	0.0167 (7)	0.0140 (7)	0.0023 (6)	0.0011 (6)	−0.0049 (5)
O2W	0.0174 (8)	0.0347 (9)	0.0155 (7)	0.0048 (7)	0.0001 (6)	−0.0119 (6)
O3W	0.0190 (8)	0.0352 (9)	0.0148 (7)	0.0039 (7)	−0.0031 (6)	−0.0111 (6)
O4W	0.0209 (8)	0.0176 (7)	0.0162 (7)	0.0037 (6)	−0.0026 (6)	−0.0067 (6)

O1A—C1A	1.233 (3)	N1B—C2B	1.422 (2)
O2A—C5A	1.247 (2)	N1B—H1BA	0.86
O3A—C6A	1.226 (2)	N2B—C4B	1.305 (3)
N1A—C1A	1.358 (2)	N2B—C3B	1.372 (2)
N1A—C2A	1.426 (2)	N3B—C4B	1.355 (2)
N1A—H1AA	0.86	N3B—C5B	1.397 (2)
N2A—C4A	1.302 (3)	N3B—H3BA	0.86
N2A—C3A	1.372 (3)	N4B—C6B	1.382 (3)
N3A—C4A	1.354 (2)	N4B—C4B	1.382 (2)
N3A—C5A	1.403 (2)	N4B—H4BA	0.86
N3A—H3AA	0.86	N5B—C3B	1.336 (2)
N4A—C6A	1.378 (3)	N5B—H5BA	0.86
N4A—C4A	1.387 (2)	N5B—H5BB	0.86
N4A—H4AA	0.86	C1B—C11B	1.529 (3)
N5A—C3A	1.335 (3)	C2B—C3B	1.404 (3)
N5A—H5AA	0.86	C2B—C5B	1.407 (3)
N5A—H5AB	0.86	C6B—C7B	1.527 (3)
C1A—C11A	1.534 (3)	C7B—C8B	1.533 (3)
C2A—C5A	1.403 (3)	C7B—C10B	1.535 (3)
C2A—C3A	1.406 (3)	C7B—C9B	1.539 (3)
C6A—C7A	1.531 (3)	C8B—H8BA	0.96
C7A—C8A	1.527 (3)	C8B—H8BB	0.96
C7A—C10A	1.538 (3)	C8B—H8BC	0.96
C7A—C9A	1.538 (3)	C9B—H9BA	0.96
C8A—H8AA	0.96	C9B—H9BB	0.96
C8A—H8AB	0.96	C9B—H9BC	0.96
C8A—H8AC	0.96	C10B—H10D	0.96
C9A—H9AA	0.96	C10B—H10E	0.96
C9A—H9AB	0.96	C10B—H10F	0.96
C9A—H9AC	0.96	C11B—C14B	1.527 (3)
C10A—H10A	0.96	C11B—C13B	1.536 (3)
C10A—H10B	0.96	C11B—C12B	1.537 (3)
C10A—H10C	0.96	C12B—H12D	0.96
C11A—C14A	1.526 (3)	C12B—H12E	0.96
C11A—C13A	1.528 (3)	C12B—H12F	0.96
C11A—C12A	1.539 (3)	C13B—H13D	0.96
C12A—H12A	0.96	C13B—H13E	0.96
C12A—H12B	0.96	C13B—H13F	0.96
C12A—H12C	0.96	C14B—H14D	0.96
C13A—H13A	0.96	C14B—H14E	0.96
C13A—H13B	0.96	C14B—H14F	0.96
C13A—H13C	0.96	O1W—H1W1	0.87
C14A—H14A	0.96	O1W—H2W1	0.90
C14A—H14B	0.96	O2W—H1W2	0.87
C14A—H14C	0.96	O2W—H2W2	0.89
O1B—C1B	1.229 (3)	O3W—H1W3	0.85
O2B—C5B	1.247 (2)	O3W—H2W3	0.89
O3B—C6B	1.225 (3)	O4W—H1W4	0.88
N1B—C1B	1.357 (3)	O4W—H2W4	0.88
C1A—N1A—C2A	122.09 (17)	C2B—N1B—H1BA	118.9
C1A—N1A—H1AA	119.0	C4B—N2B—C3B	116.57 (16)
C2A—N1A—H1AA	119.0	C4B—N3B—C5B	122.21 (17)
C4A—N2A—C3A	116.50 (16)	C4B—N3B—H3BA	118.9
C4A—N3A—C5A	122.14 (17)	C5B—N3B—H3BA	118.9
C4A—N3A—H3AA	118.9	C6B—N4B—C4B	126.21 (17)
C5A—N3A—H3AA	118.9	C6B—N4B—H4BA	116.9
C6A—N4A—C4A	126.41 (17)	C4B—N4B—H4BA	116.9
C6A—N4A—H4AA	116.8	C3B—N5B—H5BA	120.0
C4A—N4A—H4AA	116.8	C3B—N5B—H5BB	120.0
C3A—N5A—H5AA	120.0	H5BA—N5B—H5BB	120.0
C3A—N5A—H5AB	120.0	O1B—C1B—N1B	121.35 (18)
H5AA—N5A—H5AB	120.0	O1B—C1B—C11B	119.82 (18)
O1A—C1A—N1A	120.91 (18)	N1B—C1B—C11B	118.79 (18)
O1A—C1A—C11A	120.20 (18)	C3B—C2B—C5B	119.80 (17)
N1A—C1A—C11A	118.84 (18)	C3B—C2B—N1B	121.26 (17)
C5A—C2A—C3A	119.52 (17)	C5B—C2B—N1B	118.87 (17)
C5A—C2A—N1A	119.35 (17)	N5B—C3B—N2B	115.08 (17)
C3A—C2A—N1A	121.09 (17)	N5B—C3B—C2B	122.54 (18)
N5A—C3A—N2A	114.99 (17)	N2B—C3B—C2B	122.38 (17)
N5A—C3A—C2A	122.35 (18)	N2B—C4B—N3B	124.38 (18)
N2A—C3A—C2A	122.64 (18)	N2B—C4B—N4B	117.28 (17)
N2A—C4A—N3A	124.42 (18)	N3B—C4B—N4B	118.33 (17)
N2A—C4A—N4A	117.21 (17)	O2B—C5B—N3B	117.56 (18)
N3A—C4A—N4A	118.35 (17)	O2B—C5B—C2B	127.85 (18)
O2A—C5A—N3A	117.72 (18)	N3B—C5B—C2B	114.59 (17)
O2A—C5A—C2A	127.59 (18)	O3B—C6B—N4B	122.21 (18)
N3A—C5A—C2A	114.70 (17)	O3B—C6B—C7B	122.76 (19)
O3A—C6A—N4A	121.84 (18)	N4B—C6B—C7B	115.02 (17)
O3A—C6A—C7A	123.05 (18)	C6B—C7B—C8B	108.78 (17)
N4A—C6A—C7A	115.10 (17)	C6B—C7B—C10B	109.49 (19)
C8A—C7A—C6A	108.48 (17)	C8B—C7B—C10B	109.59 (19)
C8A—C7A—C10A	109.87 (19)	C6B—C7B—C9B	109.57 (18)
C6A—C7A—C10A	109.06 (18)	C8B—C7B—C9B	109.16 (19)
C8A—C7A—C9A	109.16 (19)	C10B—C7B—C9B	110.22 (19)
C6A—C7A—C9A	109.61 (18)	C7B—C8B—H8BA	109.5
C10A—C7A—C9A	110.63 (18)	C7B—C8B—H8BB	109.5
C7A—C8A—H8AA	109.5	H8BA—C8B—H8BB	109.5
C7A—C8A—H8AB	109.5	C7B—C8B—H8BC	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BC	109.5
C7A—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	C7B—C9B—H9BA	109.5
H8AB—C8A—H8AC	109.5	C7B—C9B—H9BB	109.5
C7A—C9A—H9AA	109.5	H9BA—C9B—H9BB	109.5
C7A—C9A—H9AB	109.5	C7B—C9B—H9BC	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BC	109.5
C7A—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	C7B—C10B—H10D	109.5
H9AB—C9A—H9AC	109.5	C7B—C10B—H10E	109.5
C7A—C10A—H10A	109.5	H10D—C10B—H10E	109.5
C7A—C10A—H10B	109.5	C7B—C10B—H10F	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10F	109.5
C7A—C10A—H10C	109.5	H10E—C10B—H10F	109.5
H10A—C10A—H10C	109.5	C14B—C11B—C1B	114.60 (18)
H10B—C10A—H10C	109.5	C14B—C11B—C13B	109.37 (19)
C14A—C11A—C13A	109.63 (19)	C1B—C11B—C13B	108.17 (17)
C14A—C11A—C1A	114.71 (17)	C14B—C11B—C12B	109.6 (2)
C13A—C11A—C1A	107.86 (18)	C1B—C11B—C12B	104.75 (18)
C14A—C11A—C12A	109.2 (2)	C13B—C11B—C12B	110.2 (2)
C13A—C11A—C12A	110.5 (2)	C11B—C12B—H12D	109.5
C1A—C11A—C12A	104.87 (18)	C11B—C12B—H12E	109.5
C11A—C12A—H12A	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12F	109.5
C11A—C12A—H12C	109.5	H12E—C12B—H12F	109.5
H12A—C12A—H12C	109.5	C11B—C13B—H13D	109.5
H12B—C12A—H12C	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13A	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13F	109.5
C11A—C13A—H13C	109.5	H13E—C13B—H13F	109.5
H13A—C13A—H13C	109.5	C11B—C14B—H14D	109.5
H13B—C13A—H13C	109.5	C11B—C14B—H14E	109.5
C11A—C14A—H14A	109.5	H14D—C14B—H14E	109.5
C11A—C14A—H14B	109.5	C11B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14F	109.5
C11A—C14A—H14C	109.5	H14E—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H1W1—O1W—H2W1	93.9
H14B—C14A—H14C	109.5	H1W2—O2W—H2W2	100.6
C1B—N1B—C2B	122.25 (17)	H1W3—O3W—H2W3	103.4
C1B—N1B—H1BA	118.9	H1W4—O4W—H2W4	100.7
C2A—N1A—C1A—O1A	−0.1 (3)	C2B—N1B—C1B—O1B	0.7 (3)
C2A—N1A—C1A—C11A	177.39 (17)	C2B—N1B—C1B—C11B	−177.27 (17)
C1A—N1A—C2A—C5A	−106.0 (2)	C1B—N1B—C2B—C3B	−70.7 (3)
C1A—N1A—C2A—C3A	71.8 (3)	C1B—N1B—C2B—C5B	106.3 (2)
C4A—N2A—C3A—N5A	178.46 (18)	C4B—N2B—C3B—N5B	−178.07 (18)
C4A—N2A—C3A—C2A	−2.9 (3)	C4B—N2B—C3B—C2B	2.5 (3)
C5A—C2A—C3A—N5A	179.67 (19)	C5B—C2B—C3B—N5B	−179.83 (19)
N1A—C2A—C3A—N5A	1.9 (3)	N1B—C2B—C3B—N5B	−2.9 (3)
C5A—C2A—C3A—N2A	1.2 (3)	C5B—C2B—C3B—N2B	−0.4 (3)
N1A—C2A—C3A—N2A	−176.57 (19)	N1B—C2B—C3B—N2B	176.56 (18)
C3A—N2A—C4A—N3A	2.1 (3)	C3B—N2B—C4B—N3B	−2.3 (3)
C3A—N2A—C4A—N4A	−176.13 (18)	C3B—N2B—C4B—N4B	176.55 (17)
C5A—N3A—C4A—N2A	0.5 (3)	C5B—N3B—C4B—N2B	0.0 (3)
C5A—N3A—C4A—N4A	178.75 (18)	C5B—N3B—C4B—N4B	−178.80 (18)
C6A—N4A—C4A—N2A	172.1 (2)	C6B—N4B—C4B—N2B	−172.0 (2)
C6A—N4A—C4A—N3A	−6.3 (3)	C6B—N4B—C4B—N3B	6.9 (3)
C4A—N3A—C5A—O2A	177.46 (19)	C4B—N3B—C5B—O2B	−178.21 (19)
C4A—N3A—C5A—C2A	−2.3 (3)	C4B—N3B—C5B—C2B	2.0 (3)
C3A—C2A—C5A—O2A	−178.3 (2)	C3B—C2B—C5B—O2B	178.5 (2)
N1A—C2A—C5A—O2A	−0.5 (3)	N1B—C2B—C5B—O2B	1.4 (3)
C3A—C2A—C5A—N3A	1.4 (3)	C3B—C2B—C5B—N3B	−1.8 (3)
N1A—C2A—C5A—N3A	179.19 (17)	N1B—C2B—C5B—N3B	−178.80 (17)
C4A—N4A—C6A—O3A	12.3 (3)	C4B—N4B—C6B—O3B	−12.1 (3)
C4A—N4A—C6A—C7A	−166.52 (19)	C4B—N4B—C6B—C7B	167.13 (19)
O3A—C6A—C7A—C8A	−1.9 (3)	O3B—C6B—C7B—C8B	2.4 (3)
N4A—C6A—C7A—C8A	176.91 (19)	N4B—C6B—C7B—C8B	−176.8 (2)
O3A—C6A—C7A—C10A	−121.5 (2)	O3B—C6B—C7B—C10B	122.1 (2)
N4A—C6A—C7A—C10A	57.3 (2)	N4B—C6B—C7B—C10B	−57.1 (2)
O3A—C6A—C7A—C9A	117.2 (2)	O3B—C6B—C7B—C9B	−116.9 (2)
N4A—C6A—C7A—C9A	−64.0 (2)	N4B—C6B—C7B—C9B	63.9 (2)
O1A—C1A—C11A—C14A	−173.80 (19)	O1B—C1B—C11B—C14B	175.6 (2)
N1A—C1A—C11A—C14A	8.7 (3)	N1B—C1B—C11B—C14B	−6.4 (3)
O1A—C1A—C11A—C13A	−51.3 (3)	O1B—C1B—C11B—C13B	53.3 (3)
N1A—C1A—C11A—C13A	131.2 (2)	N1B—C1B—C11B—C13B	−128.7 (2)
O1A—C1A—C11A—C12A	66.4 (3)	O1B—C1B—C11B—C12B	−64.3 (2)
N1A—C1A—C11A—C12A	−111.1 (2)	N1B—C1B—C11B—C12B	113.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4AA···O1Wi	0.86	2.07	2.918 (2)	167
N4B—H4BA···O4Wii	0.86	2.08	2.920 (2)	166
N5B—H5BA···O4Wiii	0.86	2.32	3.160 (2)	166
N5B—H5BB···O1Aiv	0.86	2.09	2.861 (2)	149
O1W—H1W1···O2Wv	0.87	2.00	2.857 (2)	167
O1W—H2W1···O2Wvi	0.90	1.92	2.819 (2)	178
O2W—H2W2···O2Bv	0.89	1.96	2.824 (2)	162
O3W—H1W3···O2Aiii	0.86	1.91	2.722 (2)	158
O3W—H2W3···O2Avii	0.89	1.97	2.833 (2)	162
O4W—H1W4···O3Wviii	0.88	1.99	2.865 (2)	174
N3A—H3AA···O3A	0.86	1.98	2.633 (2)	132
N5A—H5AA···O1W	0.86	2.32	3.163 (2)	167
N5A—H5AB···O1B	0.86	2.08	2.854 (2)	149
N3B—H3BA···O3B	0.86	1.97	2.632 (2)	132
O2W—H1W2···O2B	0.87	1.91	2.717 (2)	154
O4W—H2W4···O3W	0.88	1.93	2.811 (2)	173
C14A—H14A···O1B	0.96	2.53	3.355 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4A—H4AA⋯O1Wi	0.86	2.07	2.918 (2)	167
N4B—H4BA⋯O4Wii	0.86	2.08	2.920 (2)	166
N5B—H5BA⋯O4Wiii	0.86	2.32	3.160 (2)	166
N5B—H5BB⋯O1Aiv	0.86	2.09	2.861 (2)	149
O1W—H1W1⋯O2Wv	0.87	2.00	2.857 (2)	167
O1W—H2W1⋯O2Wvi	0.90	1.92	2.819 (2)	178
O2W—H2W2⋯O2Bv	0.89	1.96	2.824 (2)	162
O3W—H1W3⋯O2Aiii	0.86	1.91	2.722 (2)	158
O3W—H2W3⋯O2Avii	0.89	1.97	2.833 (2)	162
O4W—H1W4⋯O3Wviii	0.88	1.99	2.865 (2)	174
N3A—H3AA⋯O3A	0.86	1.98	2.633 (2)	132
N5A—H5AA⋯O1W	0.86	2.32	3.163 (2)	167
N5A—H5AB⋯O1B	0.86	2.08	2.854 (2)	149
N3B—H3BA⋯O3B	0.86	1.97	2.632 (2)	132
O2W—H1W2⋯O2B	0.87	1.91	2.717 (2)	154
O4W—H2W4⋯O3W	0.88	1.93	2.811 (2)	173
C14A—H14A⋯O1B	0.96	2.53	3.355 (3)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .