Amicarbazone.

Three independent mol-ecules comprise the asymmetric unit of the title compound, C10H19N5O2, (systematic name: 4-amino-N-tert-butyl-3-isopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide) . In all three mol-ecules, the triazole ring and the carboxamide group are almost coplanar [within 4.0-5.9 (9)°], particularly because of the formation of an intra-molecular N-H⋯O hydrogen bond. On other hand, the orientation of the isopropyl group varies significantly from mol-ecule to mol-ecule. The crystal packing is dominated by N-H⋯O and N-H⋯N hydrogen bonds, which connect the mol-ecules into infinite chains along [010].

Related literature

For herbicidal properties of amicarbazone and for its preparation, see: Dayan et al. (2009 ▶); Diehr (1998 ▶). For related structures, see: Crockett et al. (2004 ▶); Dupont et al. (1991 ▶); Heng et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H19N5O2

M = 241.30

Triclinic,

a = 11.0298 (2) Å

b = 12.2135 (4) Å

c = 14.8542 (4) Å

α = 92.244 (2)°

β = 95.7020 (19)°

γ = 93.379 (2)°

V = 1985.65 (9) Å3

Z = 6

Cu Kα radiation

μ = 0.72 mm−1

T = 123 K

0.35 × 0.25 × 0.15 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.791, T max = 1.000

13380 measured reflections

7959 independent reflections

7592 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 1.05

7959 reflections

499 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007782/ld2097sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007782/ld2097Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007782/ld2097Isup3.cml

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

C10H19N5O2	Z = 6
Mr = 241.30	F(000) = 780
Triclinic, P1	Dx = 1.211 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 11.0298 (2) Å	Cell parameters from 11341 reflections
b = 12.2135 (4) Å	θ = 3.0–75.4°
c = 14.8542 (4) Å	µ = 0.72 mm−1
α = 92.244 (2)°	T = 123 K
β = 95.7020 (19)°	Prism, colorless
γ = 93.379 (2)°	0.35 × 0.25 × 0.15 mm
V = 1985.65 (9) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	7959 independent reflections
Radiation source: Enhance (Cu) X-ray Source	7592 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 10.5081 pixels mm-1	θmax = 75.6°, θmin = 3.0°
ω scans	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −13→15
Tmin = 0.791, Tmax = 1.000	l = −17→18
13380 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.6558P] where P = (Fo2 + 2Fc2)/3
7959 reflections	(Δ/σ)max < 0.001
499 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.51333 (8)	0.54857 (7)	0.27512 (6)	0.02404 (19)
O2A	0.79068 (9)	0.61028 (9)	0.49492 (7)	0.0338 (2)
N1A	0.40274 (9)	0.61234 (8)	0.39102 (7)	0.0195 (2)
N2A	0.28358 (9)	0.60744 (9)	0.34749 (8)	0.0228 (2)
H3N1	0.2623 (16)	0.5362 (16)	0.3316 (12)	0.032 (4)*
H3N2	0.2814 (17)	0.6526 (16)	0.2999 (13)	0.035 (4)*
N3A	0.55089 (9)	0.64321 (9)	0.50255 (7)	0.0223 (2)
N4A	0.59586 (9)	0.60225 (8)	0.42386 (7)	0.0212 (2)
N5A	0.75776 (9)	0.56285 (9)	0.34326 (8)	0.0242 (2)
H4AB	0.6995	0.5513	0.2983	0.029*
C1A	0.50547 (10)	0.58304 (9)	0.35331 (8)	0.0196 (2)
C2A	0.43486 (11)	0.64838 (9)	0.47960 (8)	0.0201 (2)
C3A	0.34541 (11)	0.69354 (10)	0.53838 (9)	0.0237 (3)
H4AA	0.2738	0.6391	0.5371	0.028*
C4A	0.30062 (13)	0.80053 (12)	0.50000 (10)	0.0315 (3)
H5AA	0.2599	0.7854	0.4387	0.047*
H5AB	0.3704	0.8535	0.4979	0.047*
H5AC	0.2429	0.8309	0.5389	0.047*
C5A	0.40205 (14)	0.71189 (12)	0.63627 (9)	0.0305 (3)
H6AA	0.4295	0.6423	0.6590	0.046*
H6AB	0.3411	0.7393	0.6737	0.046*
H6AC	0.4719	0.7658	0.6389	0.046*
C6A	0.72576 (11)	0.59224 (10)	0.42504 (9)	0.0233 (2)
C7A	0.88576 (11)	0.54861 (11)	0.32375 (10)	0.0271 (3)
C8A	0.96498 (13)	0.65373 (13)	0.34987 (12)	0.0372 (3)
H9AA	0.9690	0.6685	0.4155	0.056*
H9AB	0.9294	0.7151	0.3184	0.056*
H9AC	1.0474	0.6451	0.3325	0.056*
C9A	0.93520 (13)	0.45147 (13)	0.37431 (11)	0.0363 (3)
H10A	0.9283	0.4631	0.4392	0.054*
H10B	1.0211	0.4452	0.3644	0.054*
H10C	0.8879	0.3838	0.3517	0.054*
C10A	0.87979 (14)	0.52432 (15)	0.22191 (11)	0.0389 (3)
H11A	0.8453	0.5857	0.1898	0.058*
H11B	0.8281	0.4571	0.2055	0.058*
H11C	0.9622	0.5145	0.2049	0.058*
O1B	0.32055 (8)	0.95985 (7)	0.03184 (6)	0.02541 (19)
O2B	0.15234 (8)	0.69360 (7)	0.16012 (6)	0.0269 (2)
N1B	0.46600 (9)	0.93184 (8)	0.15285 (7)	0.0201 (2)
N2B	0.54880 (10)	1.02214 (9)	0.14557 (8)	0.0242 (2)
H3B2	0.5068 (16)	1.0854 (15)	0.1505 (12)	0.030 (4)*
H3B1	0.5749 (17)	1.0154 (15)	0.0910 (13)	0.034 (4)*
N3B	0.37300 (9)	0.79451 (8)	0.21715 (7)	0.0221 (2)
N4B	0.30260 (9)	0.82468 (8)	0.13967 (7)	0.0211 (2)
N5B	0.12373 (10)	0.81232 (9)	0.04498 (7)	0.0258 (2)
H4BB	0.1620	0.8634	0.0162	0.031*
C1B	0.35739 (11)	0.91208 (10)	0.09966 (8)	0.0206 (2)
C2B	0.46927 (11)	0.86178 (10)	0.22317 (8)	0.0208 (2)
C3B	0.56869 (12)	0.86298 (10)	0.29937 (9)	0.0261 (3)
H4BA	0.5476	0.8016	0.3388	0.031*
C4B	0.69240 (13)	0.84177 (13)	0.26659 (12)	0.0381 (3)
H5BA	0.6867	0.7711	0.2323	0.057*
H5BB	0.7538	0.8401	0.3189	0.057*
H5BC	0.7161	0.9005	0.2275	0.057*
C5B	0.57330 (15)	0.96978 (12)	0.35741 (10)	0.0354 (3)
H6BA	0.4919	0.9814	0.3757	0.053*
H6BB	0.5999	1.0314	0.3222	0.053*
H6BC	0.6311	0.9649	0.4114	0.053*
C6B	0.18508 (11)	0.77003 (10)	0.11635 (8)	0.0214 (2)
C7B	−0.00412 (14)	0.77871 (12)	0.01138 (11)	0.0363 (3)
C8B	−0.08729 (15)	0.80880 (16)	0.08385 (15)	0.0514 (5)
H9BA	−0.0789	0.8883	0.0972	0.077*
H9BB	−0.0640	0.7705	0.1391	0.077*
H9BC	−0.1723	0.7869	0.0617	0.077*
C9B	−0.0174 (2)	0.65528 (15)	−0.01308 (14)	0.0556 (5)
H10D	0.0374	0.6378	−0.0589	0.083*
H10E	−0.1019	0.6345	−0.0372	0.083*
H10F	0.0038	0.6145	0.0412	0.083*
C10B	−0.0332 (2)	0.84417 (17)	−0.07255 (14)	0.0600 (6)
H11D	0.0175	0.8216	−0.1197	0.090*
H11E	−0.0162	0.9227	−0.0570	0.090*
H11F	−0.1196	0.8303	−0.0948	0.090*
O1C	0.18247 (8)	0.38918 (7)	0.24910 (6)	0.02389 (19)
O2C	0.32253 (9)	0.07163 (7)	0.25786 (7)	0.0297 (2)
N1C	0.33153 (9)	0.40112 (8)	0.14853 (7)	0.0196 (2)
N2C	0.32178 (11)	0.51004 (9)	0.12243 (8)	0.0232 (2)
H3C2	0.3638 (16)	0.5511 (15)	0.1687 (12)	0.030 (4)*
H3C1	0.2454 (19)	0.5268 (16)	0.1224 (13)	0.039 (5)*
N3C	0.40591 (9)	0.23804 (9)	0.16020 (7)	0.0222 (2)
N4C	0.31110 (9)	0.24896 (8)	0.21498 (7)	0.0200 (2)
N5C	0.17403 (10)	0.17616 (8)	0.30715 (7)	0.0227 (2)
H4CB	0.1416	0.2398	0.3002	0.027*
C1C	0.26465 (11)	0.35096 (10)	0.21013 (8)	0.0192 (2)
C2C	0.41530 (11)	0.33083 (10)	0.12170 (8)	0.0201 (2)
C3C	0.50113 (12)	0.35820 (10)	0.05267 (8)	0.0234 (2)
H4CA	0.5188	0.4396	0.0556	0.028*
C4C	0.62141 (13)	0.30430 (13)	0.07196 (11)	0.0349 (3)
H5CA	0.6552	0.3228	0.1346	0.052*
H5CB	0.6792	0.3309	0.0305	0.052*
H5CC	0.6073	0.2245	0.0632	0.052*
C5C	0.43789 (14)	0.32422 (13)	−0.04145 (9)	0.0346 (3)
H6CA	0.3638	0.3642	−0.0527	0.052*
H6CB	0.4160	0.2451	−0.0447	0.052*
H6CC	0.4933	0.3415	−0.0873	0.052*
C6C	0.27048 (11)	0.15583 (10)	0.26283 (8)	0.0208 (2)
C7C	0.11856 (12)	0.09791 (10)	0.36725 (9)	0.0257 (3)
C8C	0.07780 (17)	−0.01067 (13)	0.31583 (12)	0.0425 (4)
H9CA	0.1492	−0.0449	0.2957	0.064*
H9CB	0.0209	0.0029	0.2631	0.064*
H9CC	0.0371	−0.0597	0.3557	0.064*
C9C	0.21050 (15)	0.08115 (13)	0.44839 (10)	0.0356 (3)
H10G	0.2817	0.0472	0.4276	0.053*
H10H	0.1725	0.0331	0.4904	0.053*
H10I	0.2363	0.1523	0.4793	0.053*
C10C	0.00908 (15)	0.15331 (13)	0.39930 (12)	0.0402 (4)
H11G	0.0366	0.2242	0.4299	0.060*
H11H	−0.0301	0.1064	0.4415	0.060*
H11I	−0.0496	0.1649	0.3470	0.060*

	U11	U22	U33	U12	U13	U23
O1A	0.0203 (4)	0.0274 (4)	0.0250 (4)	0.0057 (3)	0.0033 (3)	−0.0002 (3)
O2A	0.0208 (4)	0.0459 (6)	0.0339 (5)	0.0082 (4)	−0.0026 (4)	−0.0038 (4)
N1A	0.0158 (5)	0.0186 (5)	0.0244 (5)	0.0027 (4)	0.0026 (4)	0.0020 (4)
N2A	0.0144 (5)	0.0250 (5)	0.0287 (5)	0.0030 (4)	0.0003 (4)	0.0006 (4)
N3A	0.0208 (5)	0.0224 (5)	0.0246 (5)	0.0050 (4)	0.0040 (4)	0.0009 (4)
N4A	0.0171 (5)	0.0221 (5)	0.0249 (5)	0.0052 (4)	0.0035 (4)	0.0010 (4)
N5A	0.0155 (5)	0.0280 (5)	0.0297 (5)	0.0044 (4)	0.0032 (4)	0.0028 (4)
C1A	0.0166 (5)	0.0164 (5)	0.0266 (6)	0.0031 (4)	0.0036 (4)	0.0045 (4)
C2A	0.0208 (6)	0.0157 (5)	0.0247 (6)	0.0026 (4)	0.0038 (4)	0.0037 (4)
C3A	0.0217 (6)	0.0226 (6)	0.0280 (6)	0.0032 (5)	0.0073 (5)	0.0004 (5)
C4A	0.0333 (7)	0.0283 (7)	0.0341 (7)	0.0140 (5)	0.0036 (6)	−0.0015 (5)
C5A	0.0368 (7)	0.0288 (7)	0.0272 (6)	0.0071 (5)	0.0069 (5)	0.0009 (5)
C6A	0.0160 (6)	0.0211 (6)	0.0332 (7)	0.0050 (4)	0.0022 (5)	0.0036 (5)
C7A	0.0173 (6)	0.0293 (7)	0.0365 (7)	0.0057 (5)	0.0075 (5)	0.0044 (5)
C8A	0.0201 (6)	0.0352 (8)	0.0571 (9)	0.0007 (5)	0.0088 (6)	0.0016 (7)
C9A	0.0255 (7)	0.0365 (8)	0.0501 (9)	0.0132 (6)	0.0109 (6)	0.0102 (6)
C10A	0.0283 (7)	0.0515 (9)	0.0388 (8)	0.0049 (6)	0.0124 (6)	0.0011 (7)
O1B	0.0264 (4)	0.0276 (5)	0.0227 (4)	0.0022 (4)	0.0015 (3)	0.0088 (3)
O2B	0.0252 (4)	0.0241 (4)	0.0314 (5)	−0.0006 (3)	0.0015 (4)	0.0074 (4)
N1B	0.0200 (5)	0.0179 (5)	0.0230 (5)	0.0025 (4)	0.0027 (4)	0.0027 (4)
N2B	0.0236 (5)	0.0193 (5)	0.0302 (6)	−0.0007 (4)	0.0045 (4)	0.0040 (4)
N3B	0.0222 (5)	0.0221 (5)	0.0220 (5)	0.0042 (4)	−0.0005 (4)	0.0051 (4)
N4B	0.0208 (5)	0.0220 (5)	0.0205 (5)	0.0020 (4)	0.0003 (4)	0.0052 (4)
N5B	0.0237 (5)	0.0282 (5)	0.0249 (5)	−0.0014 (4)	−0.0011 (4)	0.0062 (4)
C1B	0.0211 (6)	0.0202 (5)	0.0214 (5)	0.0038 (4)	0.0051 (4)	0.0017 (4)
C2B	0.0222 (6)	0.0177 (5)	0.0231 (6)	0.0054 (4)	0.0024 (4)	0.0024 (4)
C3B	0.0265 (6)	0.0220 (6)	0.0286 (6)	0.0036 (5)	−0.0052 (5)	0.0040 (5)
C4B	0.0259 (7)	0.0384 (8)	0.0491 (9)	0.0114 (6)	−0.0060 (6)	0.0020 (6)
C5B	0.0417 (8)	0.0307 (7)	0.0311 (7)	0.0070 (6)	−0.0101 (6)	−0.0026 (6)
C6B	0.0212 (6)	0.0212 (6)	0.0219 (6)	0.0026 (4)	0.0029 (4)	0.0006 (4)
C7B	0.0317 (7)	0.0334 (7)	0.0396 (8)	−0.0063 (6)	−0.0143 (6)	0.0074 (6)
C8B	0.0243 (7)	0.0490 (10)	0.0815 (14)	0.0017 (7)	0.0040 (8)	0.0148 (9)
C9B	0.0708 (13)	0.0385 (9)	0.0495 (10)	−0.0147 (8)	−0.0227 (9)	−0.0014 (7)
C10B	0.0620 (12)	0.0555 (11)	0.0538 (11)	−0.0152 (9)	−0.0334 (9)	0.0199 (9)
O1C	0.0243 (4)	0.0211 (4)	0.0284 (4)	0.0056 (3)	0.0095 (3)	0.0046 (3)
O2C	0.0361 (5)	0.0217 (4)	0.0348 (5)	0.0100 (4)	0.0133 (4)	0.0084 (4)
N1C	0.0209 (5)	0.0180 (5)	0.0207 (5)	0.0024 (4)	0.0038 (4)	0.0036 (4)
N2C	0.0261 (6)	0.0181 (5)	0.0265 (5)	0.0040 (4)	0.0047 (4)	0.0066 (4)
N3C	0.0222 (5)	0.0221 (5)	0.0240 (5)	0.0036 (4)	0.0085 (4)	0.0023 (4)
N4C	0.0205 (5)	0.0195 (5)	0.0213 (5)	0.0038 (4)	0.0060 (4)	0.0036 (4)
N5C	0.0254 (5)	0.0197 (5)	0.0252 (5)	0.0052 (4)	0.0074 (4)	0.0081 (4)
C1C	0.0199 (5)	0.0187 (5)	0.0187 (5)	0.0009 (4)	0.0006 (4)	0.0027 (4)
C2C	0.0204 (6)	0.0198 (5)	0.0202 (5)	0.0017 (4)	0.0022 (4)	0.0003 (4)
C3C	0.0261 (6)	0.0207 (6)	0.0245 (6)	−0.0005 (5)	0.0091 (5)	0.0019 (4)
C4C	0.0281 (7)	0.0365 (7)	0.0432 (8)	0.0047 (6)	0.0152 (6)	0.0083 (6)
C5C	0.0383 (8)	0.0413 (8)	0.0243 (6)	−0.0086 (6)	0.0101 (6)	0.0004 (6)
C6C	0.0244 (6)	0.0193 (6)	0.0189 (5)	0.0021 (4)	0.0016 (4)	0.0045 (4)
C7C	0.0281 (6)	0.0231 (6)	0.0281 (6)	0.0027 (5)	0.0094 (5)	0.0098 (5)
C8C	0.0496 (9)	0.0309 (8)	0.0464 (9)	−0.0112 (7)	0.0099 (7)	0.0037 (6)
C9C	0.0412 (8)	0.0385 (8)	0.0292 (7)	0.0065 (6)	0.0063 (6)	0.0150 (6)
C10C	0.0350 (8)	0.0403 (8)	0.0512 (9)	0.0100 (6)	0.0222 (7)	0.0198 (7)

O1A—C1A	1.2329 (15)	C4B—H5BA	0.9800
O2A—C6A	1.2061 (16)	C4B—H5BB	0.9800
N1A—C1A	1.3725 (15)	C4B—H5BC	0.9800
N1A—C2A	1.3764 (16)	C5B—H6BA	0.9800
N1A—N2A	1.4028 (14)	C5B—H6BB	0.9800
N2A—H3N1	0.904 (19)	C5B—H6BC	0.9800
N2A—H3N2	0.91 (2)	C7B—C10B	1.525 (2)
N3A—C2A	1.2971 (16)	C7B—C8B	1.530 (3)
N3A—N4A	1.4004 (14)	C7B—C9B	1.532 (2)
N4A—C1A	1.3757 (16)	C8B—H9BA	0.9800
N4A—C6A	1.4435 (15)	C8B—H9BB	0.9800
N5A—C6A	1.3398 (17)	C8B—H9BC	0.9800
N5A—C7A	1.4879 (15)	C9B—H10D	0.9800
N5A—H4AB	0.8800	C9B—H10E	0.9800
C2A—C3A	1.4959 (16)	C9B—H10F	0.9800
C3A—C5A	1.5271 (19)	C10B—H11D	0.9800
C3A—C4A	1.5346 (18)	C10B—H11E	0.9800
C3A—H4AA	1.0000	C10B—H11F	0.9800
C4A—H5AA	0.9800	O1C—C1C	1.2278 (15)
C4A—H5AB	0.9800	O2C—C6C	1.2103 (16)
C4A—H5AC	0.9800	N1C—C1C	1.3717 (15)
C5A—H6AA	0.9800	N1C—C2C	1.3746 (16)
C5A—H6AB	0.9800	N1C—N2C	1.4072 (14)
C5A—H6AC	0.9800	N2C—H3C2	0.906 (18)
C7A—C10A	1.524 (2)	N2C—H3C1	0.88 (2)
C7A—C8A	1.524 (2)	N3C—C2C	1.2926 (16)
C7A—C9A	1.5276 (19)	N3C—N4C	1.3967 (14)
C8A—H9AA	0.9800	N4C—C1C	1.3764 (15)
C8A—H9AB	0.9800	N4C—C6C	1.4373 (15)
C8A—H9AC	0.9800	N5C—C6C	1.3358 (16)
C9A—H10A	0.9800	N5C—C7C	1.4802 (15)
C9A—H10B	0.9800	N5C—H4CB	0.8800
C9A—H10C	0.9800	C2C—C3C	1.4972 (16)
C10A—H11A	0.9800	C3C—C4C	1.5224 (19)
C10A—H11B	0.9800	C3C—C5C	1.5298 (19)
C10A—H11C	0.9800	C3C—H4CA	1.0000
O1B—C1B	1.2301 (15)	C4C—H5CA	0.9800
O2B—C6B	1.2161 (15)	C4C—H5CB	0.9800
N1B—C1B	1.3713 (16)	C4C—H5CC	0.9800
N1B—C2B	1.3750 (15)	C5C—H6CA	0.9800
N1B—N2B	1.4044 (14)	C5C—H6CB	0.9800
N2B—H3B2	0.929 (19)	C5C—H6CC	0.9800
N2B—H3B1	0.89 (2)	C7C—C9C	1.5243 (19)
N3B—C2B	1.2973 (17)	C7C—C8C	1.525 (2)
N3B—N4B	1.3974 (14)	C7C—C10C	1.5258 (19)
N4B—C1B	1.3794 (16)	C8C—H9CA	0.9800
N4B—C6B	1.4270 (16)	C8C—H9CB	0.9800
N5B—C6B	1.3380 (16)	C8C—H9CC	0.9800
N5B—C7B	1.4771 (17)	C9C—H10G	0.9800
N5B—H4BB	0.8800	C9C—H10H	0.9800
C2B—C3B	1.4948 (17)	C9C—H10I	0.9800
C3B—C4B	1.526 (2)	C10C—H11G	0.9800
C3B—C5B	1.5306 (19)	C10C—H11H	0.9800
C3B—H4BA	1.0000	C10C—H11I	0.9800
C1A—N1A—C2A	109.01 (10)	C3B—C5B—H6BB	109.5
C1A—N1A—N2A	126.31 (10)	H6BA—C5B—H6BB	109.5
C2A—N1A—N2A	124.69 (10)	C3B—C5B—H6BC	109.5
N1A—N2A—H3N1	107.3 (11)	H6BA—C5B—H6BC	109.5
N1A—N2A—H3N2	109.0 (12)	H6BB—C5B—H6BC	109.5
H3N1—N2A—H3N2	114.1 (16)	O2B—C6B—N5B	127.90 (12)
C2A—N3A—N4A	104.12 (10)	O2B—C6B—N4B	119.55 (11)
C1A—N4A—N3A	112.25 (9)	N5B—C6B—N4B	112.54 (10)
C1A—N4A—C6A	129.36 (10)	N5B—C7B—C10B	105.72 (13)
N3A—N4A—C6A	118.27 (10)	N5B—C7B—C8B	109.22 (13)
C6A—N5A—C7A	123.99 (11)	C10B—C7B—C8B	110.02 (16)
C6A—N5A—H4AB	118.0	N5B—C7B—C9B	110.28 (14)
C7A—N5A—H4AB	118.0	C10B—C7B—C9B	110.52 (15)
O1A—C1A—N1A	127.90 (11)	C8B—C7B—C9B	110.95 (15)
O1A—C1A—N4A	129.20 (11)	C7B—C8B—H9BA	109.5
N1A—C1A—N4A	102.90 (10)	C7B—C8B—H9BB	109.5
N3A—C2A—N1A	111.70 (10)	H9BA—C8B—H9BB	109.5
N3A—C2A—C3A	125.55 (11)	C7B—C8B—H9BC	109.5
N1A—C2A—C3A	122.66 (11)	H9BA—C8B—H9BC	109.5
C2A—C3A—C5A	111.00 (11)	H9BB—C8B—H9BC	109.5
C2A—C3A—C4A	109.25 (10)	C7B—C9B—H10D	109.5
C5A—C3A—C4A	111.24 (11)	C7B—C9B—H10E	109.5
C2A—C3A—H4AA	108.4	H10D—C9B—H10E	109.5
C5A—C3A—H4AA	108.4	C7B—C9B—H10F	109.5
C4A—C3A—H4AA	108.4	H10D—C9B—H10F	109.5
C3A—C4A—H5AA	109.5	H10E—C9B—H10F	109.5
C3A—C4A—H5AB	109.5	C7B—C10B—H11D	109.5
H5AA—C4A—H5AB	109.5	C7B—C10B—H11E	109.5
C3A—C4A—H5AC	109.5	H11D—C10B—H11E	109.5
H5AA—C4A—H5AC	109.5	C7B—C10B—H11F	109.5
H5AB—C4A—H5AC	109.5	H11D—C10B—H11F	109.5
C3A—C5A—H6AA	109.5	H11E—C10B—H11F	109.5
C3A—C5A—H6AB	109.5	C1C—N1C—C2C	109.08 (10)
H6AA—C5A—H6AB	109.5	C1C—N1C—N2C	125.18 (10)
C3A—C5A—H6AC	109.5	C2C—N1C—N2C	125.58 (10)
H6AA—C5A—H6AC	109.5	N1C—N2C—H3C2	104.3 (11)
H6AB—C5A—H6AC	109.5	N1C—N2C—H3C1	108.9 (12)
O2A—C6A—N5A	128.31 (12)	H3C2—N2C—H3C1	105.8 (17)
O2A—C6A—N4A	119.58 (12)	C2C—N3C—N4C	104.58 (10)
N5A—C6A—N4A	112.11 (11)	C1C—N4C—N3C	111.95 (9)
N5A—C7A—C10A	105.80 (11)	C1C—N4C—C6C	128.99 (10)
N5A—C7A—C8A	110.33 (11)	N3C—N4C—C6C	118.94 (10)
C10A—C7A—C8A	109.89 (12)	C6C—N5C—C7C	123.83 (10)
N5A—C7A—C9A	109.66 (11)	C6C—N5C—H4CB	118.1
C10A—C7A—C9A	109.83 (12)	C7C—N5C—H4CB	118.1
C8A—C7A—C9A	111.18 (12)	O1C—C1C—N1C	127.35 (11)
C7A—C8A—H9AA	109.5	O1C—C1C—N4C	129.76 (11)
C7A—C8A—H9AB	109.5	N1C—C1C—N4C	102.87 (10)
H9AA—C8A—H9AB	109.5	N3C—C2C—N1C	111.48 (10)
C7A—C8A—H9AC	109.5	N3C—C2C—C3C	125.19 (11)
H9AA—C8A—H9AC	109.5	N1C—C2C—C3C	123.25 (11)
H9AB—C8A—H9AC	109.5	C2C—C3C—C4C	111.38 (11)
C7A—C9A—H10A	109.5	C2C—C3C—C5C	108.67 (10)
C7A—C9A—H10B	109.5	C4C—C3C—C5C	112.05 (12)
H10A—C9A—H10B	109.5	C2C—C3C—H4CA	108.2
C7A—C9A—H10C	109.5	C4C—C3C—H4CA	108.2
H10A—C9A—H10C	109.5	C5C—C3C—H4CA	108.2
H10B—C9A—H10C	109.5	C3C—C4C—H5CA	109.5
C7A—C10A—H11A	109.5	C3C—C4C—H5CB	109.5
C7A—C10A—H11B	109.5	H5CA—C4C—H5CB	109.5
H11A—C10A—H11B	109.5	C3C—C4C—H5CC	109.5
C7A—C10A—H11C	109.5	H5CA—C4C—H5CC	109.5
H11A—C10A—H11C	109.5	H5CB—C4C—H5CC	109.5
H11B—C10A—H11C	109.5	C3C—C5C—H6CA	109.5
C1B—N1B—C2B	108.91 (10)	C3C—C5C—H6CB	109.5
C1B—N1B—N2B	124.54 (10)	H6CA—C5C—H6CB	109.5
C2B—N1B—N2B	125.57 (10)	C3C—C5C—H6CC	109.5
N1B—N2B—H3B2	107.8 (11)	H6CA—C5C—H6CC	109.5
N1B—N2B—H3B1	106.6 (12)	H6CB—C5C—H6CC	109.5
H3B2—N2B—H3B1	110.3 (16)	O2C—C6C—N5C	128.46 (11)
C2B—N3B—N4B	104.24 (10)	O2C—C6C—N4C	119.36 (11)
C1B—N4B—N3B	112.05 (10)	N5C—C6C—N4C	112.16 (10)
C1B—N4B—C6B	129.10 (10)	N5C—C7C—C9C	109.05 (11)
N3B—N4B—C6B	118.67 (10)	N5C—C7C—C8C	110.71 (11)
C6B—N5B—C7B	124.13 (11)	C9C—C7C—C8C	111.28 (12)
C6B—N5B—H4BB	117.9	N5C—C7C—C10C	105.50 (10)
C7B—N5B—H4BB	117.9	C9C—C7C—C10C	109.49 (12)
O1B—C1B—N1B	127.81 (11)	C8C—C7C—C10C	110.63 (13)
O1B—C1B—N4B	129.22 (11)	C7C—C8C—H9CA	109.5
N1B—C1B—N4B	102.95 (10)	C7C—C8C—H9CB	109.5
N3B—C2B—N1B	111.74 (11)	H9CA—C8C—H9CB	109.5
N3B—C2B—C3B	123.07 (11)	C7C—C8C—H9CC	109.5
N1B—C2B—C3B	125.18 (11)	H9CA—C8C—H9CC	109.5
C2B—C3B—C4B	112.37 (11)	H9CB—C8C—H9CC	109.5
C2B—C3B—C5B	110.69 (11)	C7C—C9C—H10G	109.5
C4B—C3B—C5B	111.95 (12)	C7C—C9C—H10H	109.5
C2B—C3B—H4BA	107.2	H10G—C9C—H10H	109.5
C4B—C3B—H4BA	107.2	C7C—C9C—H10I	109.5
C5B—C3B—H4BA	107.2	H10G—C9C—H10I	109.5
C3B—C4B—H5BA	109.5	H10H—C9C—H10I	109.5
C3B—C4B—H5BB	109.5	C7C—C10C—H11G	109.5
H5BA—C4B—H5BB	109.5	C7C—C10C—H11H	109.5
C3B—C4B—H5BC	109.5	H11G—C10C—H11H	109.5
H5BA—C4B—H5BC	109.5	C7C—C10C—H11I	109.5
H5BB—C4B—H5BC	109.5	H11G—C10C—H11I	109.5
C3B—C5B—H6BA	109.5	H11H—C10C—H11I	109.5
C2A—N3A—N4A—C1A	0.10 (13)	N2B—N1B—C2B—C3B	−6.47 (19)
C2A—N3A—N4A—C6A	176.55 (10)	N3B—C2B—C3B—C4B	120.86 (14)
C2A—N1A—C1A—O1A	−178.86 (12)	N1B—C2B—C3B—C4B	−60.80 (16)
N2A—N1A—C1A—O1A	0.90 (19)	N3B—C2B—C3B—C5B	−113.15 (14)
C2A—N1A—C1A—N4A	0.84 (12)	N1B—C2B—C3B—C5B	65.18 (17)
N2A—N1A—C1A—N4A	−179.39 (10)	C7B—N5B—C6B—O2B	6.4 (2)
N3A—N4A—C1A—O1A	179.11 (11)	C7B—N5B—C6B—N4B	−174.12 (12)
C6A—N4A—C1A—O1A	3.2 (2)	C1B—N4B—C6B—O2B	179.99 (12)
N3A—N4A—C1A—N1A	−0.59 (12)	N3B—N4B—C6B—O2B	−5.26 (17)
C6A—N4A—C1A—N1A	−176.55 (11)	C1B—N4B—C6B—N5B	0.45 (18)
N4A—N3A—C2A—N1A	0.46 (13)	N3B—N4B—C6B—N5B	175.21 (10)
N4A—N3A—C2A—C3A	−176.14 (11)	C6B—N5B—C7B—C10B	−177.48 (15)
C1A—N1A—C2A—N3A	−0.86 (13)	C6B—N5B—C7B—C8B	64.18 (17)
N2A—N1A—C2A—N3A	179.37 (10)	C6B—N5B—C7B—C9B	−57.99 (19)
C1A—N1A—C2A—C3A	175.85 (10)	C2C—N3C—N4C—C1C	−1.08 (13)
N2A—N1A—C2A—C3A	−3.92 (17)	C2C—N3C—N4C—C6C	175.35 (10)
N3A—C2A—C3A—C5A	−11.65 (17)	C2C—N1C—C1C—O1C	179.41 (12)
N1A—C2A—C3A—C5A	172.11 (11)	N2C—N1C—C1C—O1C	3.8 (2)
N3A—C2A—C3A—C4A	111.38 (14)	C2C—N1C—C1C—N4C	−1.73 (12)
N1A—C2A—C3A—C4A	−64.86 (15)	N2C—N1C—C1C—N4C	−177.36 (10)
C7A—N5A—C6A—O2A	−1.1 (2)	N3C—N4C—C1C—O1C	−179.44 (12)
C7A—N5A—C6A—N4A	178.68 (11)	C6C—N4C—C1C—O1C	4.6 (2)
C1A—N4A—C6A—O2A	−178.10 (12)	N3C—N4C—C1C—N1C	1.74 (13)
N3A—N4A—C6A—O2A	6.15 (17)	C6C—N4C—C1C—N1C	−174.23 (11)
C1A—N4A—C6A—N5A	2.10 (18)	N4C—N3C—C2C—N1C	−0.09 (13)
N3A—N4A—C6A—N5A	−173.65 (10)	N4C—N3C—C2C—C3C	−177.01 (11)
C6A—N5A—C7A—C10A	−175.58 (12)	C1C—N1C—C2C—N3C	1.21 (14)
C6A—N5A—C7A—C8A	−56.76 (17)	N2C—N1C—C2C—N3C	176.81 (11)
C6A—N5A—C7A—C9A	66.03 (16)	C1C—N1C—C2C—C3C	178.20 (11)
C2B—N3B—N4B—C1B	−0.70 (13)	N2C—N1C—C2C—C3C	−6.20 (18)
C2B—N3B—N4B—C6B	−176.31 (10)	N3C—C2C—C3C—C4C	−35.08 (17)
C2B—N1B—C1B—O1B	178.39 (12)	N1C—C2C—C3C—C4C	148.34 (12)
N2B—N1B—C1B—O1B	9.2 (2)	N3C—C2C—C3C—C5C	88.83 (15)
C2B—N1B—C1B—N4B	−3.08 (12)	N1C—C2C—C3C—C5C	−87.75 (14)
N2B—N1B—C1B—N4B	−172.31 (10)	C7C—N5C—C6C—O2C	5.9 (2)
N3B—N4B—C1B—O1B	−179.14 (12)	C7C—N5C—C6C—N4C	−175.50 (11)
C6B—N4B—C1B—O1B	−4.1 (2)	C1C—N4C—C6C—O2C	178.93 (12)
N3B—N4B—C1B—N1B	2.37 (13)	N3C—N4C—C6C—O2C	3.20 (17)
C6B—N4B—C1B—N1B	177.41 (11)	C1C—N4C—C6C—N5C	0.15 (18)
N4B—N3B—C2B—N1B	−1.35 (13)	N3C—N4C—C6C—N5C	−175.58 (10)
N4B—N3B—C2B—C3B	177.19 (11)	C6C—N5C—C7C—C9C	64.87 (16)
C1B—N1B—C2B—N3B	2.95 (14)	C6C—N5C—C7C—C8C	−57.90 (17)
N2B—N1B—C2B—N3B	172.03 (11)	C6C—N5C—C7C—C10C	−177.61 (13)
C1B—N1B—C2B—C3B	−175.55 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H3N1···O1C	0.904 (19)	2.220 (19)	3.0832 (14)	159.6 (15)
N2A—H3N2···N3B	0.91 (2)	2.40 (2)	3.2251 (15)	150.9 (15)
N2A—H3N2···O2B	0.91 (2)	2.483 (19)	3.2492 (14)	141.7 (15)
N5A—H4AB···O1A	0.88	2.05	2.7770 (14)	140
N2B—H3B2···N3Ci	0.929 (19)	2.233 (19)	3.1619 (15)	179.1 (15)
N2B—H3B1···O1Bii	0.89 (2)	2.27 (2)	3.1356 (15)	163.1 (16)
N5B—H4BB···O1B	0.88	2.04	2.7655 (14)	139
N2C—H3C2···O1A	0.906 (18)	2.171 (18)	2.9455 (15)	143.1 (15)
N2C—H3C1···O2B	0.88 (2)	2.41 (2)	3.0718 (14)	132.8 (16)
N5C—H4CB···O1C	0.88	2.05	2.7721 (13)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H3N1⋯O1C	0.904 (19)	2.220 (19)	3.0832 (14)	159.6 (15)
N2A—H3N2⋯N3B	0.91 (2)	2.40 (2)	3.2251 (15)	150.9 (15)
N2A—H3N2⋯O2B	0.91 (2)	2.483 (19)	3.2492 (14)	141.7 (15)
N5A—H4AB⋯O1A	0.88	2.05	2.7770 (14)	140
N2B—H3B2⋯N3C i	0.929 (19)	2.233 (19)	3.1619 (15)	179.1 (15)
N2B—H3B1⋯O1B ii	0.89 (2)	2.27 (2)	3.1356 (15)	163.1 (16)
N5B—H4BB⋯O1B	0.88	2.04	2.7655 (14)	139
N2C—H3C2⋯O1A	0.906 (18)	2.171 (18)	2.9455 (15)	143.1 (15)
N2C—H3C1⋯O2B	0.88 (2)	2.41 (2)	3.0718 (14)	132.8 (16)
N5C—H4CB⋯O1C	0.88	2.05	2.7721 (13)	139

Symmetry codes: (i) ; (ii) .