N-[2-(2,2-Di-methyl-propanamido)-pyrimidin-4-yl]-2,2-di-methyl-propanamide n-hexane 0.25-solvate hemihydrate.

The asymmetric unit of the title compound, C14H22N4O2·0.25C6H14·0.5H2O, contains two independent mol-ecules of 2,4-bis-(pivaloyl-amino)-pyrimidine (M) with similar conformations, one water mol-ecule and one-half n-hexane solvent mol-ecule situated on an inversion center. In one independent M mol-ecule, one of the two tert-butyl groups is rotationally disordered between two orientations in a 3:2 ratio. The n-hexane solvent mol-ecule is disordered between two conformations in the same ratio. The water mol-ecule bridges two independent M mol-ecules via O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds into a 2M·H2O unit, and these units are further linked by N-H⋯N hydrogen bonds into chains running in the [010] direction. Weak C-H⋯O inter-actions are observed between the adjacent chains.

Related literature

For the related structures of 2,4-bis­(acyl­oamino)­pyrimidines in the solid state and in solution, see: Ośmiałowski et al. (2012 ▶). For the related structures of 2,6-bis­(acyl­oamino)­pyridines, see: Ośmiałowski et al. (2010 ▶); Crane (2003 ▶).

Experimental

Crystal data

2C14H22N4O2·0.5C6H14·H2O

M = 617.81

Triclinic,

a = 10.6055 (5) Å

b = 12.2181 (6) Å

c = 14.9774 (7) Å

α = 88.060 (3)°

β = 73.093 (4)°

γ = 74.179 (3)°

V = 1784.36 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.30 × 0.05 × 0.04 mm

Data collection

Bruker–Nonius KappaCCD diffractometer with an APEXII detector

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.977, T max = 0.997

21621 measured reflections

6422 independent reflections

3597 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.164

S = 1.04

6422 reflections

451 parameters

101 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Bruker, 2008 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681302713X/cv5431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302713X/cv5431Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302713X/cv5431Isup3.cml

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

2C14H22N4O2·0.5C6H14·H2O	Z = 2
Mr = 617.81	F(000) = 670
Triclinic, P1	Dx = 1.150 Mg m−3
a = 10.6055 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2181 (6) Å	Cell parameters from 7150 reflections
c = 14.9774 (7) Å	θ = 0.4–28.3°
α = 88.060 (3)°	µ = 0.08 mm−1
β = 73.093 (4)°	T = 123 K
γ = 74.179 (3)°	Needle, colourless
V = 1784.36 (16) Å3	0.30 × 0.05 × 0.04 mm

Bruker–Nonius KappaCCD with APEXII detector diffractometer	6422 independent reflections
Radiation source: fine-focus sealed tube	3597 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
Detector resolution: 9 pixels mm-1	θmax = 25.3°, θmin = 2.3°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −14→14
Tmin = 0.977, Tmax = 0.997	l = −16→17
21621 measured reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0128P)2 + 3.1862P] where P = (Fo2 + 2Fc2)/3
6422 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.35 e Å−3
101 restraints	Δρmin = −0.24 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O8	0.3412 (3)	0.46261 (19)	0.05984 (17)	0.0307 (6)
O14	0.4845 (3)	0.3749 (2)	0.46471 (17)	0.0358 (7)
N1	0.3512 (3)	0.5088 (2)	0.2372 (2)	0.0233 (7)
N3	0.3818 (3)	0.6952 (2)	0.2389 (2)	0.0285 (8)
N7	0.3042 (3)	0.6391 (2)	0.1249 (2)	0.0256 (7)
H7	0.287 (4)	0.7128 (17)	0.117 (2)	0.031*
N13	0.4056 (3)	0.3746 (2)	0.3391 (2)	0.0262 (7)
H13	0.395 (4)	0.333 (3)	0.297 (2)	0.031*
C2	0.3483 (4)	0.6108 (3)	0.2042 (2)	0.0234 (8)
C4	0.4134 (4)	0.6713 (3)	0.3196 (3)	0.0304 (9)
H4	0.4324	0.7296	0.3496	0.037*
C5	0.4204 (4)	0.5693 (3)	0.3616 (3)	0.0266 (9)
H5	0.4425	0.5559	0.4188	0.032*
C6	0.3925 (4)	0.4870 (3)	0.3142 (2)	0.0240 (8)
C8	0.3040 (4)	0.5661 (3)	0.0571 (2)	0.0235 (8)
C9	0.2520 (4)	0.6243 (3)	−0.0223 (2)	0.0241 (8)
C10	0.3278 (5)	0.7128 (4)	−0.0646 (3)	0.0516 (13)
H10A	0.3121	0.7713	−0.0163	0.077*
H10B	0.2935	0.7483	−0.1157	0.077*
H10C	0.4262	0.6754	−0.0887	0.077*
C11	0.0990 (4)	0.6824 (4)	0.0157 (3)	0.0479 (12)
H11A	0.0835	0.7404	0.0642	0.072*
H11B	0.0506	0.6256	0.0424	0.072*
H11C	0.0644	0.7184	−0.0352	0.072*
C12	0.2773 (5)	0.5344 (3)	−0.0978 (3)	0.0490 (12)
H12A	0.2445	0.5706	−0.1493	0.073*
H12B	0.2281	0.4780	−0.0717	0.073*
H12C	0.3757	0.4966	−0.1211	0.073*
C14	0.4569 (4)	0.3226 (3)	0.4087 (2)	0.0249 (8)
C15	0.4773 (4)	0.1939 (3)	0.4109 (3)	0.0348 (10)
C16	0.3527 (12)	0.1542 (14)	0.4115 (16)	0.049 (4)	0.6
H16A	0.3759	0.0709	0.4125	0.074*	0.6
H16B	0.3252	0.1788	0.3554	0.074*	0.6
H16C	0.2769	0.1873	0.4672	0.074*	0.6
C17	0.580 (3)	0.145 (2)	0.3155 (10)	0.051 (4)	0.6
H17A	0.5968	0.0616	0.3125	0.077*	0.6
H17B	0.6658	0.1637	0.3080	0.077*	0.6
H17C	0.5409	0.1770	0.2653	0.077*	0.6
C18	0.5496 (13)	0.1468 (16)	0.4841 (8)	0.055 (4)	0.6
H18A	0.5631	0.0642	0.4858	0.083*	0.6
H18B	0.4934	0.1826	0.5455	0.083*	0.6
H18C	0.6388	0.1632	0.4680	0.083*	0.6
C16B	0.3332 (17)	0.182 (2)	0.425 (2)	0.049 (5)	0.4
H16G	0.3356	0.1015	0.4267	0.074*	0.4
H16H	0.2996	0.2159	0.3728	0.074*	0.4
H16I	0.2719	0.2221	0.4837	0.074*	0.4
C17B	0.596 (4)	0.128 (3)	0.3298 (18)	0.057 (6)	0.4
H17G	0.6042	0.0467	0.3344	0.085*	0.4
H17H	0.6810	0.1432	0.3322	0.085*	0.4
H17I	0.5782	0.1533	0.2706	0.085*	0.4
C18B	0.493 (2)	0.162 (2)	0.5081 (10)	0.057 (5)	0.4
H18G	0.5070	0.0797	0.5141	0.086*	0.4
H18H	0.4102	0.2028	0.5563	0.086*	0.4
H18I	0.5723	0.1829	0.5158	0.086*	0.4
O8A	0.5012 (3)	0.06266 (19)	0.11110 (18)	0.0308 (6)
O14A	−0.1719 (3)	0.2917 (2)	0.2818 (2)	0.0401 (7)
N1A	0.2274 (3)	0.0794 (2)	0.2012 (2)	0.0241 (7)
N3A	0.1930 (3)	−0.0951 (2)	0.1596 (2)	0.0291 (8)
N7A	0.4086 (3)	−0.0859 (2)	0.1563 (2)	0.0278 (7)
H7A	0.424 (4)	−0.1590 (17)	0.163 (3)	0.033*
N13A	0.0596 (3)	0.2457 (2)	0.2438 (2)	0.0278 (7)
H13A	0.134 (3)	0.268 (3)	0.238 (3)	0.033*
C2A	0.2704 (4)	−0.0302 (3)	0.1724 (2)	0.0246 (8)
C4A	0.0594 (4)	−0.0408 (3)	0.1783 (3)	0.0319 (9)
H4A	−0.0004	−0.0836	0.1721	0.038*
C5A	0.0030 (4)	0.0726 (3)	0.2060 (3)	0.0296 (9)
H5A	−0.0920	0.1087	0.2172	0.035*
C6A	0.0941 (4)	0.1311 (3)	0.2166 (2)	0.0258 (9)
C8A	0.5165 (4)	−0.0389 (3)	0.1257 (2)	0.0236 (8)
C9A	0.6589 (4)	−0.1224 (3)	0.1082 (2)	0.0245 (8)
C10A	0.6809 (4)	−0.2132 (3)	0.0330 (3)	0.0382 (10)
H10D	0.7725	−0.2662	0.0219	0.057*
H10E	0.6728	−0.1764	−0.0250	0.057*
H10F	0.6116	−0.2550	0.0541	0.057*
C11A	0.6756 (4)	−0.1802 (3)	0.1980 (3)	0.0378 (10)
H11D	0.7674	−0.2333	0.1852	0.057*
H11E	0.6065	−0.2219	0.2205	0.057*
H11F	0.6638	−0.1223	0.2457	0.057*
C12A	0.7650 (4)	−0.0561 (3)	0.0739 (3)	0.0340 (10)
H12D	0.8572	−0.1083	0.0619	0.051*
H12E	0.7513	0.0024	0.1217	0.051*
H12F	0.7548	−0.0196	0.0162	0.051*
C14A	−0.0697 (4)	0.3197 (3)	0.2778 (2)	0.0283 (9)
C15A	−0.0712 (4)	0.4379 (3)	0.3093 (3)	0.0303 (9)
C16A	0.0042 (5)	0.4278 (4)	0.3835 (3)	0.0526 (13)
H16D	0.0024	0.5039	0.4034	0.079*
H16E	0.0994	0.3825	0.3573	0.079*
H16F	−0.0411	0.3904	0.4375	0.079*
C17A	0.0004 (4)	0.4968 (3)	0.2252 (3)	0.0396 (11)
H17D	−0.0007	0.5725	0.2455	0.059*
H17E	−0.0480	0.5043	0.1776	0.059*
H17F	0.0954	0.4511	0.1987	0.059*
C18A	−0.2197 (4)	0.5074 (3)	0.3492 (3)	0.0453 (11)
H18D	−0.2227	0.5835	0.3699	0.068*
H18E	−0.2655	0.4693	0.4023	0.068*
H18F	−0.2666	0.5141	0.3009	0.068*
O1	0.3274 (3)	0.2837 (2)	0.19608 (18)	0.0267 (6)
H1A	0.367 (4)	0.219 (2)	0.168 (2)	0.040*
H1B	0.341 (4)	0.336 (3)	0.161 (2)	0.040*
C19	0.0268 (6)	0.7745 (4)	0.3857 (4)	0.0705 (16)
H19A	0.0798	0.6973	0.3935	0.106*	0.6
H19B	0.0354	0.7854	0.3193	0.106*	0.6
H19C	−0.0699	0.7851	0.4205	0.106*	0.6
H19D	0.0647	0.6924	0.3894	0.106*	0.4
H19E	0.0794	0.8003	0.3278	0.106*	0.4
H19F	−0.0692	0.7906	0.3865	0.106*	0.4
C20	0.0808 (9)	0.8604 (8)	0.4226 (8)	0.062 (3)	0.6
H20A	0.1341	0.8212	0.4644	0.074*	0.6
H20B	0.1455	0.8850	0.3690	0.074*	0.6
C20B	0.0356 (16)	0.8381 (9)	0.4706 (8)	0.057 (4)	0.4
H20C	−0.0158	0.8098	0.5287	0.068*	0.4
H20D	0.1327	0.8194	0.4701	0.068*	0.4
C21	−0.0176 (6)	0.9607 (4)	0.4725 (4)	0.0702 (16)
H21A	−0.0932	0.9351	0.5157	0.084*	0.6
H21B	−0.0562	1.0066	0.4261	0.084*	0.6
H21C	−0.1187	0.9775	0.4932	0.084*	0.4
H21D	0.0081	0.9829	0.4069	0.084*	0.4

	U11	U22	U33	U12	U13	U23
O8	0.0437 (18)	0.0156 (13)	0.0338 (15)	−0.0028 (12)	−0.0177 (13)	0.0011 (11)
O14	0.0485 (19)	0.0318 (15)	0.0313 (15)	−0.0069 (13)	−0.0216 (14)	−0.0006 (12)
N1	0.0280 (19)	0.0180 (15)	0.0295 (17)	−0.0078 (13)	−0.0159 (14)	0.0030 (13)
N3	0.034 (2)	0.0175 (16)	0.0382 (19)	−0.0080 (14)	−0.0167 (16)	0.0020 (14)
N7	0.032 (2)	0.0144 (15)	0.0355 (18)	−0.0059 (14)	−0.0184 (15)	0.0034 (14)
N13	0.039 (2)	0.0172 (16)	0.0276 (17)	−0.0072 (14)	−0.0189 (15)	0.0037 (13)
C2	0.027 (2)	0.0165 (18)	0.030 (2)	−0.0055 (16)	−0.0129 (17)	0.0023 (15)
C4	0.031 (2)	0.023 (2)	0.040 (2)	−0.0082 (17)	−0.0135 (19)	−0.0071 (17)
C5	0.029 (2)	0.025 (2)	0.030 (2)	−0.0089 (17)	−0.0129 (18)	0.0015 (16)
C6	0.023 (2)	0.0225 (19)	0.026 (2)	−0.0062 (16)	−0.0078 (17)	0.0005 (16)
C8	0.019 (2)	0.023 (2)	0.027 (2)	−0.0051 (16)	−0.0056 (16)	0.0030 (16)
C9	0.026 (2)	0.0224 (18)	0.0233 (19)	−0.0047 (16)	−0.0092 (16)	0.0057 (15)
C10	0.068 (3)	0.045 (3)	0.053 (3)	−0.028 (2)	−0.026 (3)	0.023 (2)
C11	0.034 (3)	0.061 (3)	0.042 (3)	0.004 (2)	−0.016 (2)	0.010 (2)
C12	0.068 (3)	0.036 (2)	0.039 (2)	0.004 (2)	−0.027 (2)	−0.002 (2)
C14	0.021 (2)	0.0254 (19)	0.026 (2)	−0.0057 (16)	−0.0052 (17)	0.0038 (16)
C15	0.046 (3)	0.025 (2)	0.046 (2)	−0.0164 (18)	−0.027 (2)	0.0111 (18)
C16	0.047 (6)	0.034 (8)	0.084 (8)	−0.021 (5)	−0.036 (6)	0.010 (6)
C17	0.055 (7)	0.016 (6)	0.081 (7)	0.006 (4)	−0.033 (5)	0.000 (5)
C18	0.069 (8)	0.041 (7)	0.082 (7)	−0.025 (7)	−0.056 (6)	0.032 (6)
C16B	0.056 (8)	0.026 (9)	0.063 (9)	−0.024 (7)	−0.003 (7)	0.017 (7)
C17B	0.050 (10)	0.031 (11)	0.088 (11)	−0.007 (8)	−0.020 (10)	0.002 (9)
C18B	0.087 (13)	0.044 (8)	0.058 (8)	−0.015 (11)	−0.052 (8)	0.020 (7)
O8A	0.0267 (16)	0.0167 (13)	0.0484 (16)	−0.0057 (11)	−0.0105 (13)	0.0062 (11)
O14A	0.0256 (17)	0.0328 (16)	0.061 (2)	−0.0081 (13)	−0.0100 (14)	−0.0021 (13)
N1A	0.0225 (19)	0.0166 (15)	0.0345 (17)	−0.0053 (13)	−0.0103 (14)	0.0016 (13)
N3A	0.030 (2)	0.0208 (16)	0.0425 (19)	−0.0107 (15)	−0.0159 (16)	0.0030 (14)
N7A	0.0260 (19)	0.0146 (15)	0.047 (2)	−0.0060 (14)	−0.0175 (16)	0.0045 (14)
N13A	0.023 (2)	0.0195 (16)	0.0410 (19)	−0.0089 (14)	−0.0061 (16)	−0.0016 (14)
C2A	0.026 (2)	0.0202 (19)	0.030 (2)	−0.0070 (17)	−0.0110 (17)	0.0066 (16)
C4A	0.031 (3)	0.026 (2)	0.047 (2)	−0.0133 (18)	−0.019 (2)	0.0019 (18)
C5A	0.022 (2)	0.025 (2)	0.043 (2)	−0.0055 (17)	−0.0113 (18)	−0.0041 (17)
C6A	0.026 (2)	0.0202 (19)	0.031 (2)	−0.0051 (17)	−0.0103 (17)	0.0018 (16)
C8A	0.026 (2)	0.0194 (19)	0.0271 (19)	−0.0041 (16)	−0.0131 (17)	0.0006 (15)
C9A	0.024 (2)	0.0181 (18)	0.033 (2)	−0.0031 (15)	−0.0123 (17)	0.0007 (15)
C10A	0.039 (3)	0.025 (2)	0.049 (3)	0.0015 (18)	−0.019 (2)	−0.0084 (18)
C11A	0.038 (3)	0.033 (2)	0.043 (2)	−0.0048 (19)	−0.018 (2)	0.0049 (19)
C12A	0.024 (2)	0.033 (2)	0.043 (2)	−0.0019 (18)	−0.0111 (19)	−0.0002 (18)
C14A	0.025 (2)	0.029 (2)	0.027 (2)	−0.0035 (18)	−0.0050 (17)	0.0010 (16)
C15A	0.028 (2)	0.029 (2)	0.033 (2)	−0.0038 (17)	−0.0112 (18)	−0.0036 (17)
C16A	0.068 (4)	0.043 (3)	0.051 (3)	−0.007 (2)	−0.030 (3)	−0.008 (2)
C17A	0.039 (3)	0.024 (2)	0.052 (3)	−0.0083 (19)	−0.008 (2)	−0.0008 (19)
C18A	0.036 (3)	0.034 (2)	0.053 (3)	−0.003 (2)	0.002 (2)	−0.013 (2)
O1	0.0328 (17)	0.0163 (13)	0.0333 (15)	−0.0067 (12)	−0.0131 (13)	0.0009 (11)
C19	0.073 (4)	0.056 (3)	0.070 (4)	−0.025 (3)	0.005 (3)	−0.013 (3)
C20	0.038 (6)	0.059 (6)	0.075 (7)	−0.017 (5)	0.007 (5)	−0.020 (6)
C20B	0.049 (10)	0.041 (7)	0.062 (9)	−0.014 (6)	0.010 (7)	0.008 (7)
C21	0.075 (4)	0.059 (3)	0.077 (4)	−0.021 (3)	−0.019 (3)	−0.007 (3)

O8—C8	1.221 (4)	N3A—C4A	1.340 (5)
O14—C14	1.216 (4)	N7A—C8A	1.373 (5)
N1—C2	1.321 (4)	N7A—C2A	1.390 (5)
N1—C6	1.343 (4)	N7A—H7A	0.871 (18)
N3—C2	1.343 (4)	N13A—C14A	1.381 (5)
N3—C4	1.347 (5)	N13A—C6A	1.391 (4)
N7—C8	1.375 (4)	N13A—H13A	0.886 (18)
N7—C2	1.398 (5)	C4A—C5A	1.375 (5)
N7—H7	0.881 (18)	C4A—H4A	0.9500
N13—C14	1.372 (5)	C5A—C6A	1.394 (5)
N13—C6	1.392 (4)	C5A—H5A	0.9500
N13—H13	0.870 (18)	C8A—C9A	1.529 (5)
C4—C5	1.370 (5)	C9A—C12A	1.523 (5)
C4—H4	0.9500	C9A—C10A	1.530 (5)
C5—C6	1.391 (5)	C9A—C11A	1.531 (5)
C5—H5	0.9500	C10A—H10D	0.9800
C8—C9	1.528 (5)	C10A—H10E	0.9800
C9—C12	1.517 (5)	C10A—H10F	0.9800
C9—C11	1.524 (5)	C11A—H11D	0.9800
C9—C10	1.532 (5)	C11A—H11E	0.9800
C10—H10A	0.9800	C11A—H11F	0.9800
C10—H10B	0.9800	C12A—H12D	0.9800
C10—H10C	0.9800	C12A—H12E	0.9800
C11—H11A	0.9800	C12A—H12F	0.9800
C11—H11B	0.9800	C14A—C15A	1.529 (5)
C11—H11C	0.9800	C15A—C18A	1.522 (5)
C12—H12A	0.9800	C15A—C16A	1.531 (5)
C12—H12B	0.9800	C15A—C17A	1.537 (5)
C12—H12C	0.9800	C16A—H16D	0.9800
C14—C15	1.529 (5)	C16A—H16E	0.9800
C15—C16	1.524 (10)	C16A—H16F	0.9800
C15—C17B	1.525 (13)	C17A—H17D	0.9800
C15—C18	1.526 (10)	C17A—H17E	0.9800
C15—C16B	1.527 (13)	C17A—H17F	0.9800
C15—C18B	1.539 (12)	C18A—H18D	0.9800
C15—C17	1.543 (10)	C18A—H18E	0.9800
C16—H16A	0.9800	C18A—H18F	0.9800
C16—H16B	0.9800	O1—H1A	0.841 (19)
C16—H16C	0.9800	O1—H1B	0.828 (18)
C17—H17A	0.9800	C19—C20	1.512 (9)
C17—H17B	0.9800	C19—C20B	1.550 (12)
C17—H17C	0.9800	C19—H19A	0.9800
C18—H18A	0.9800	C19—H19B	0.9800
C18—H18B	0.9800	C19—H19C	0.9800
C18—H18C	0.9800	C19—H19D	0.9800
C16B—H16G	0.9800	C19—H19E	0.9800
C16B—H16H	0.9800	C19—H19F	0.9800
C16B—H16I	0.9800	C20—C21	1.435 (9)
C17B—H17G	0.9800	C20—H20A	0.9900
C17B—H17H	0.9800	C20—H20B	0.9900
C17B—H17I	0.9800	C20B—C21	1.447 (11)
C18B—H18G	0.9800	C20B—H20C	0.9900
C18B—H18H	0.9800	C20B—H20D	0.9900
C18B—H18I	0.9800	C21—C21i	1.473 (10)
O8A—C8A	1.227 (4)	C21—H21A	0.9900
O14A—C14A	1.208 (4)	C21—H21B	0.9900
N1A—C2A	1.334 (4)	C21—H21C	0.9900
N1A—C6A	1.336 (5)	C21—H21D	0.9900
N3A—C2A	1.339 (4)
C2—N1—C6	116.2 (3)	C6A—N13A—H13A	111 (3)
C2—N3—C4	113.6 (3)	N1A—C2A—N3A	126.7 (3)
C8—N7—C2	127.7 (3)	N1A—C2A—N7A	117.9 (3)
C8—N7—H7	120 (2)	N3A—C2A—N7A	115.3 (3)
C2—N7—H7	112 (2)	N3A—C4A—C5A	124.4 (3)
C14—N13—C6	127.1 (3)	N3A—C4A—H4A	117.8
C14—N13—H13	120 (2)	C5A—C4A—H4A	117.8
C6—N13—H13	112 (2)	C4A—C5A—C6A	115.8 (4)
N1—C2—N3	127.5 (3)	C4A—C5A—H5A	122.1
N1—C2—N7	118.9 (3)	C6A—C5A—H5A	122.1
N3—C2—N7	113.7 (3)	N1A—C6A—N13A	112.8 (3)
N3—C4—C5	125.0 (3)	N1A—C6A—C5A	121.7 (3)
N3—C4—H4	117.5	N13A—C6A—C5A	125.5 (3)
C5—C4—H4	117.5	O8A—C8A—N7A	122.8 (3)
C4—C5—C6	114.9 (3)	O8A—C8A—C9A	121.7 (3)
C4—C5—H5	122.5	N7A—C8A—C9A	115.4 (3)
C6—C5—H5	122.5	C12A—C9A—C8A	108.2 (3)
N1—C6—C5	122.4 (3)	C12A—C9A—C10A	109.1 (3)
N1—C6—N13	112.6 (3)	C8A—C9A—C10A	109.9 (3)
C5—C6—N13	124.9 (3)	C12A—C9A—C11A	109.5 (3)
O8—C8—N7	123.0 (3)	C8A—C9A—C11A	110.8 (3)
O8—C8—C9	122.1 (3)	C10A—C9A—C11A	109.4 (3)
N7—C8—C9	114.9 (3)	C9A—C10A—H10D	109.5
C12—C9—C11	110.0 (3)	C9A—C10A—H10E	109.5
C12—C9—C8	108.6 (3)	H10D—C10A—H10E	109.5
C11—C9—C8	108.9 (3)	C9A—C10A—H10F	109.5
C12—C9—C10	108.8 (3)	H10D—C10A—H10F	109.5
C11—C9—C10	109.6 (3)	H10E—C10A—H10F	109.5
C8—C9—C10	110.9 (3)	C9A—C11A—H11D	109.5
C9—C10—H10A	109.5	C9A—C11A—H11E	109.5
C9—C10—H10B	109.5	H11D—C11A—H11E	109.5
H10A—C10—H10B	109.5	C9A—C11A—H11F	109.5
C9—C10—H10C	109.5	H11D—C11A—H11F	109.5
H10A—C10—H10C	109.5	H11E—C11A—H11F	109.5
H10B—C10—H10C	109.5	C9A—C12A—H12D	109.5
C9—C11—H11A	109.5	C9A—C12A—H12E	109.5
C9—C11—H11B	109.5	H12D—C12A—H12E	109.5
H11A—C11—H11B	109.5	C9A—C12A—H12F	109.5
C9—C11—H11C	109.5	H12D—C12A—H12F	109.5
H11A—C11—H11C	109.5	H12E—C12A—H12F	109.5
H11B—C11—H11C	109.5	O14A—C14A—N13A	121.9 (3)
C9—C12—H12A	109.5	O14A—C14A—C15A	123.7 (3)
C9—C12—H12B	109.5	N13A—C14A—C15A	114.4 (3)
H12A—C12—H12B	109.5	C18A—C15A—C14A	108.4 (3)
C9—C12—H12C	109.5	C18A—C15A—C16A	110.2 (3)
H12A—C12—H12C	109.5	C14A—C15A—C16A	110.1 (3)
H12B—C12—H12C	109.5	C18A—C15A—C17A	109.6 (3)
O14—C14—N13	122.6 (3)	C14A—C15A—C17A	109.6 (3)
O14—C14—C15	122.2 (3)	C16A—C15A—C17A	109.0 (4)
N13—C14—C15	115.2 (3)	C15A—C16A—H16D	109.5
C16—C15—C18	117.0 (11)	C15A—C16A—H16E	109.5
C17B—C15—C16B	120 (2)	H16D—C16A—H16E	109.5
C16—C15—C14	115.5 (7)	C15A—C16A—H16F	109.5
C17B—C15—C14	112.8 (18)	H16D—C16A—H16F	109.5
C18—C15—C14	109.1 (8)	H16E—C16A—H16F	109.5
C16B—C15—C14	103.2 (10)	C15A—C17A—H17D	109.5
C17B—C15—C18B	114.3 (16)	C15A—C17A—H17E	109.5
C16B—C15—C18B	99.5 (15)	H17D—C17A—H17E	109.5
C14—C15—C18B	105.2 (12)	C15A—C17A—H17F	109.5
C16—C15—C17	102.4 (16)	H17D—C17A—H17F	109.5
C18—C15—C17	106.1 (11)	H17E—C17A—H17F	109.5
C14—C15—C17	105.5 (11)	C15A—C18A—H18D	109.5
C15—C16—H16A	109.5	C15A—C18A—H18E	109.5
C15—C16—H16B	109.5	H18D—C18A—H18E	109.5
H16A—C16—H16B	109.5	C15A—C18A—H18F	109.5
C15—C16—H16C	109.5	H18D—C18A—H18F	109.5
H16A—C16—H16C	109.5	H18E—C18A—H18F	109.5
H16B—C16—H16C	109.5	H1A—O1—H1B	111 (4)
C15—C17—H17A	109.5	C20—C19—H19A	109.5
C15—C17—H17B	109.5	C20—C19—H19B	109.5
H17A—C17—H17B	109.5	H19A—C19—H19B	109.5
C15—C17—H17C	109.5	C20—C19—H19C	109.5
H17A—C17—H17C	109.5	H19A—C19—H19C	109.5
H17B—C17—H17C	109.5	H19B—C19—H19C	109.5
C15—C18—H18A	109.5	C20B—C19—H19D	109.5
C15—C18—H18B	109.5	C20B—C19—H19E	109.5
H18A—C18—H18B	109.5	H19D—C19—H19E	109.5
C15—C18—H18C	109.5	C20B—C19—H19F	109.5
H18A—C18—H18C	109.5	H19D—C19—H19F	109.5
H18B—C18—H18C	109.5	H19E—C19—H19F	109.5
C15—C16B—H16G	109.5	C21—C20—C19	117.4 (7)
C15—C16B—H16H	109.5	C21—C20—H20A	107.9
H16G—C16B—H16H	109.5	C19—C20—H20A	107.9
C15—C16B—H16I	109.5	C21—C20—H20B	107.9
H16G—C16B—H16I	109.5	C19—C20—H20B	107.9
H16H—C16B—H16I	109.5	H20A—C20—H20B	107.2
C15—C17B—H17G	109.5	C21—C20B—C19	114.3 (9)
C15—C17B—H17H	109.5	C21—C20B—H20C	108.7
H17G—C17B—H17H	109.5	C19—C20B—H20C	108.7
C15—C17B—H17I	109.5	C21—C20B—H20D	108.7
H17G—C17B—H17I	109.5	C19—C20B—H20D	108.7
H17H—C17B—H17I	109.5	H20C—C20B—H20D	107.6
C15—C18B—H18G	109.5	C20—C21—C21i	122.8 (7)
C15—C18B—H18H	109.5	C20B—C21—C21i	123.2 (8)
H18G—C18B—H18H	109.5	C20—C21—H21A	106.6
C15—C18B—H18I	109.5	C21i—C21—H21A	106.6
H18G—C18B—H18I	109.5	C20—C21—H21B	106.6
H18H—C18B—H18I	109.5	C21i—C21—H21B	106.6
C2A—N1A—C6A	116.9 (3)	H21A—C21—H21B	106.6
C2A—N3A—C4A	114.4 (3)	C20B—C21—H21C	106.5
C8A—N7A—C2A	126.9 (3)	C21i—C21—H21C	106.5
C8A—N7A—H7A	120 (3)	C20B—C21—H21D	106.5
C2A—N7A—H7A	113 (3)	C21i—C21—H21D	106.5
C14A—N13A—C6A	127.9 (3)	H21C—C21—H21D	106.5
C14A—N13A—H13A	121 (2)
C6—N1—C2—N3	−0.1 (6)	C6A—N1A—C2A—N3A	−1.8 (5)
C6—N1—C2—N7	−179.1 (3)	C6A—N1A—C2A—N7A	−179.7 (3)
C4—N3—C2—N1	−4.2 (5)	C4A—N3A—C2A—N1A	0.0 (5)
C4—N3—C2—N7	174.9 (3)	C4A—N3A—C2A—N7A	177.9 (3)
C8—N7—C2—N1	−23.1 (6)	C8A—N7A—C2A—N1A	−31.5 (5)
C8—N7—C2—N3	157.8 (3)	C8A—N7A—C2A—N3A	150.3 (3)
C2—N3—C4—C5	3.9 (6)	C2A—N3A—C4A—C5A	1.8 (5)
N3—C4—C5—C6	0.4 (6)	N3A—C4A—C5A—C6A	−1.7 (6)
C2—N1—C6—C5	5.0 (5)	C2A—N1A—C6A—N13A	−178.2 (3)
C2—N1—C6—N13	−174.1 (3)	C2A—N1A—C6A—C5A	1.9 (5)
C4—C5—C6—N1	−5.1 (5)	C14A—N13A—C6A—N1A	−169.9 (3)
C4—C5—C6—N13	173.9 (4)	C14A—N13A—C6A—C5A	10.0 (6)
C14—N13—C6—N1	173.8 (3)	C4A—C5A—C6A—N1A	−0.3 (5)
C14—N13—C6—C5	−5.3 (6)	C4A—C5A—C6A—N13A	179.9 (3)
C2—N7—C8—O8	1.9 (6)	C2A—N7A—C8A—O8A	2.1 (6)
C2—N7—C8—C9	−178.6 (3)	C2A—N7A—C8A—C9A	−176.3 (3)
O8—C8—C9—C12	−8.7 (5)	O8A—C8A—C9A—C12A	1.1 (5)
N7—C8—C9—C12	171.8 (3)	N7A—C8A—C9A—C12A	179.4 (3)
O8—C8—C9—C11	111.1 (4)	O8A—C8A—C9A—C10A	−117.9 (4)
N7—C8—C9—C11	−68.4 (4)	N7A—C8A—C9A—C10A	60.4 (4)
O8—C8—C9—C10	−128.2 (4)	O8A—C8A—C9A—C11A	121.0 (4)
N7—C8—C9—C10	52.3 (4)	N7A—C8A—C9A—C11A	−60.6 (4)
C6—N13—C14—O14	8.2 (6)	C6A—N13A—C14A—O14A	−5.3 (6)
C6—N13—C14—C15	−171.8 (3)	C6A—N13A—C14A—C15A	174.7 (3)
O14—C14—C15—C16	127.7 (10)	O14A—C14A—C15A—C18A	2.7 (5)
N13—C14—C15—C16	−52.3 (10)	N13A—C14A—C15A—C18A	−177.3 (3)
O14—C14—C15—C17B	−109 (2)	O14A—C14A—C15A—C16A	123.3 (4)
N13—C14—C15—C17B	71 (2)	N13A—C14A—C15A—C16A	−56.7 (4)
O14—C14—C15—C18	−6.4 (7)	O14A—C14A—C15A—C17A	−116.8 (4)
N13—C14—C15—C18	173.6 (6)	N13A—C14A—C15A—C17A	63.2 (4)
O14—C14—C15—C16B	120.1 (13)	C20B—C19—C20—C21	−64.2 (11)
N13—C14—C15—C16B	−59.9 (13)	C20—C19—C20B—C21	60.4 (10)
O14—C14—C15—C18B	16.2 (10)	C19—C20—C21—C20B	65.7 (12)
N13—C14—C15—C18B	−163.8 (9)	C19—C20—C21—C21i	167.6 (7)
O14—C14—C15—C17	−120.0 (13)	C19—C20B—C21—C20	−60.0 (10)
N13—C14—C15—C17	60.0 (13)	C19—C20B—C21—C21i	−160.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O8A	0.84 (2)	2.08 (2)	2.910 (3)	167 (4)
O1—H1A···N1A	0.84 (2)	2.51 (4)	2.958 (4)	115 (3)
O1—H1B···O8	0.83 (2)	2.13 (2)	2.943 (3)	168 (4)
O1—H1B···N1	0.83 (2)	2.48 (4)	2.931 (4)	115 (3)
N7—H7···N3Aii	0.88 (2)	2.32 (2)	3.144 (4)	156 (3)
N13—H13···O1	0.87 (2)	2.02 (2)	2.864 (4)	162 (4)
N7A—H7A···N3iii	0.87 (2)	2.16 (2)	2.958 (4)	152 (3)
N13A—H13A···O1	0.89 (2)	2.02 (2)	2.882 (4)	164 (4)
C5—H5···O14iv	0.95	2.37	3.205 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O8A	0.84 (2)	2.08 (2)	2.910 (3)	167 (4)
O1—H1A⋯N1A	0.84 (2)	2.51 (4)	2.958 (4)	115 (3)
O1—H1B⋯O8	0.83 (2)	2.13 (2)	2.943 (3)	168 (4)
O1—H1B⋯N1	0.83 (2)	2.48 (4)	2.931 (4)	115 (3)
N7—H7⋯N3A i	0.88 (2)	2.32 (2)	3.144 (4)	156 (3)
N13—H13⋯O1	0.87 (2)	2.02 (2)	2.864 (4)	162 (4)
N7A—H7A⋯N3ii	0.87 (2)	2.16 (2)	2.958 (4)	152 (3)
N13A—H13A⋯O1	0.89 (2)	2.02 (2)	2.882 (4)	164 (4)
C5—H5⋯O14iii	0.95	2.37	3.205 (5)	147

Symmetry codes: (i) ; (ii) ; (iii) .