1-Acetonyl-4-(3,5-diethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

Ustabaş, R.; Çoruh, U.; Sancak, K.; Dü~gdü, E.; Vázquez-López, E.M.

doi:10.1107/S1600536806034854

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1-Acetonyl-4-(3,5-diethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

R. Ustabaş, U. Çoruh, K. Sancak, E. Dügdü and E. M. Vázquez-López

The title compound, C₁₆H₂₀N₆O₂S, has two similar independent molecules in the asymmetric unit, with planar triazole and thiophene rings. Intermolecular C—H

N and C—H

O interactions stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034854/ga2005sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034854/ga2005Isup2.hkl Contains datablock I

CCDC reference: 624522

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.052
wR factor = 0.092
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _diffrn_reflns_theta_full          26.00
           From the CIF: _reflns_number_total               6451
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         6924
           Completeness (_total/calc)             93.17%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C16 H20 N6 O2 S

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Acetonyl-4-(3,5-diethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H- 1,2,4-triazol-5(4H)-one top

Crystal data top

C₁₆H₂₀N₆O₂S	Z = 4
M_r = 360.44	F(000) = 760
Triclinic, P1	D_x = 1.360 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4340 (9) Å	Cell parameters from 3260 reflections
b = 9.8963 (11) Å	θ = 1.9–26.0°
c = 21.124 (2) Å	µ = 0.21 mm⁻¹
α = 88.989 (2)°	T = 293 K
β = 86.672 (2)°	Prism, colourless
γ = 89.909 (2)°	0.28 × 0.23 × 0.21 mm
V = 1759.9 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3260 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
φ and ω scans	h = −10→10
12473 measured reflections	k = −12→12
6451 independent reflections	l = −26→26

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0244P)²] where P = (F_o² + 2F_c²)/3
6451 reflections	(Δ/σ)_max < 0.001
457 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. IR (cm^-1): 1726 (C=O acetone), 1753 (C=O triazole), 1592 (C=N), 136–1394 (CH₂,CH₃), 696 (thiophene); ¹H NMR (δ, p.p.m.): 1.05 (6H, t, 2CH₃ triazole), 2.12–2.31 (8H, m, 2CH₂, CH₃), 4.17 (2H, s, CH₂-thiophene), 4.88 (2H, s, CH₂), 6.65–7.48 (3H, m, CH thiophene, ABC system), 2.65 (6H, s, 2CH₃), 1.82 (3H, s, CH₃ acetone); ¹³C NMR (δ, p.p.m.): 10.18 (CH₃ acetone), 16.25 (CH₂), 26.32 (CH₃) 26.71 (CH₂ thiophene), 55.09 (NCH₂), 126.44, 127.21, 127.33 (CH thiophene), 134.53 (C thiophene), 150.24 (C=N l), 143.38 (C=N), 154.24 (C=O triazole), 201.29 (C=O).

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
S1A	0.68431 (11)	0.73497 (8)	0.10901 (4)	0.0437 (2)
S1B	1.18455 (11)	−0.24023 (8)	0.10956 (4)	0.0437 (2)
O1A	0.9081 (2)	0.54268 (18)	0.35421 (9)	0.0330 (5)
O1B	1.4073 (2)	−0.06169 (18)	0.35460 (9)	0.0332 (5)
N5B	1.3616 (3)	0.2639 (2)	0.20789 (11)	0.0315 (6)
N3A	0.7203 (3)	0.5253 (2)	0.27652 (10)	0.0245 (6)
N4B	1.2504 (3)	0.0920 (2)	0.25834 (11)	0.0274 (6)
N5A	0.8591 (3)	0.2247 (2)	0.20866 (12)	0.0341 (6)
N3B	1.2197 (3)	−0.0395 (2)	0.27712 (11)	0.0273 (6)
N2A	0.7464 (3)	0.7181 (2)	0.31929 (11)	0.0282 (6)
N1A	0.6257 (3)	0.7321 (2)	0.27652 (11)	0.0280 (6)
N6A	0.7468 (3)	0.1750 (2)	0.25560 (12)	0.0340 (6)
N2B	1.2450 (3)	−0.2347 (2)	0.32031 (11)	0.0284 (6)
N4A	0.7496 (3)	0.3945 (2)	0.25870 (11)	0.0265 (6)
O2B	1.1091 (3)	−0.2361 (2)	0.44123 (10)	0.0474 (6)
N1B	1.1249 (3)	−0.2459 (2)	0.27724 (11)	0.0293 (6)
C5B	1.0040 (3)	−0.0939 (3)	0.20120 (13)	0.0320 (7)
H5B1	0.9612	−0.0041	0.2083	0.038*
H5B2	0.9159	−0.1571	0.2039	0.038*
O2A	0.6098 (3)	0.7152 (2)	0.44018 (10)	0.0476 (6)
C5A	0.5033 (3)	0.5842 (3)	0.20100 (13)	0.0314 (7)
H5A1	0.4151	0.6473	0.2034	0.038*
H5A2	0.4606	0.4941	0.2086	0.038*
C12B	1.3621 (3)	0.1333 (3)	0.21118 (13)	0.0272 (7)
C11A	0.6837 (3)	0.2787 (3)	0.28482 (14)	0.0277 (7)
C7A	0.8066 (3)	0.5913 (3)	0.32192 (14)	0.0268 (7)
C6B	1.1141 (3)	−0.1281 (3)	0.25172 (13)	0.0247 (7)
N6B	1.2484 (3)	0.3122 (2)	0.25439 (12)	0.0360 (7)
C12A	0.8606 (3)	0.3558 (3)	0.21149 (13)	0.0280 (7)
C7B	1.3054 (4)	−0.1081 (3)	0.32264 (14)	0.0275 (7)
C4B	1.0848 (3)	−0.0985 (3)	0.13554 (14)	0.0295 (7)
C11B	1.1847 (3)	0.2075 (3)	0.28392 (14)	0.0282 (7)
C13B	1.4637 (3)	0.0377 (3)	0.17381 (13)	0.0336 (8)
H12A	1.3988	−0.0363	0.1605	0.040*
H12B	1.5431	0.0002	0.2006	0.040*
C15A	0.5631 (3)	0.2748 (3)	0.33863 (14)	0.0355 (8)
H15A	0.5174	0.1848	0.3419	0.043*
H15B	0.4785	0.3374	0.3295	0.043*
C15B	1.0633 (3)	0.2094 (3)	0.33777 (14)	0.0364 (8)
H15C	0.9802	0.1454	0.3296	0.044*
H15D	1.0155	0.2986	0.3397	0.044*
C6A	0.6128 (3)	0.6155 (3)	0.25158 (13)	0.0261 (7)
C13A	0.9630 (3)	0.4529 (3)	0.17357 (13)	0.0351 (8)
H13A	1.0421	0.4888	0.2002	0.042*
H13B	0.8983	0.5278	0.1598	0.042*
C9A	0.6825 (4)	0.8158 (3)	0.42438 (14)	0.0351 (8)
C8A	0.7767 (3)	0.8265 (3)	0.36077 (13)	0.0316 (7)
H8A1	0.7508	0.9114	0.3401	0.038*
H8A2	0.8892	0.8279	0.3682	0.038*
C4A	0.5826 (3)	0.5919 (3)	0.13541 (14)	0.0317 (8)
C8B	1.2761 (3)	−0.3455 (3)	0.36281 (13)	0.0318 (8)
H8B1	1.3890	−0.3484	0.3693	0.038*
H8B2	1.2480	−0.4294	0.3432	0.038*
C9B	1.1853 (4)	−0.3359 (3)	0.42689 (15)	0.0339 (8)
C14B	1.5467 (4)	0.1045 (3)	0.11546 (14)	0.0485 (9)
H11A	1.6054	0.0377	0.0914	0.073*
H11B	1.6181	0.1728	0.1285	0.073*
H11C	1.4689	0.1452	0.0897	0.073*
C16A	0.6267 (4)	0.3102 (3)	0.40288 (14)	0.0486 (9)
H16A	0.5458	0.2934	0.4359	0.073*
H16B	0.6560	0.4039	0.4026	0.073*
H16C	0.7180	0.2555	0.4103	0.073*
C10B	1.2009 (4)	−0.4576 (3)	0.46831 (14)	0.0539 (10)
H10A	1.1526	−0.4404	0.5096	0.081*
H10B	1.3113	−0.4783	0.4718	0.081*
H10C	1.1490	−0.5328	0.4502	0.081*
C3B	1.0906 (4)	−0.0003 (3)	0.09059 (16)	0.0537 (10)
H3B	1.0416	0.0834	0.0955	0.064*
C1A	0.7364 (4)	0.6645 (3)	0.03779 (15)	0.0534 (10)
H1A	0.7963	0.7077	0.0051	0.064*
C16B	1.1280 (4)	0.1749 (3)	0.40206 (14)	0.0492 (9)
H16D	1.0465	0.1886	0.4349	0.074*
H16E	1.2169	0.2322	0.4089	0.074*
H16F	1.1614	0.0821	0.4028	0.074*
C14A	1.0463 (4)	0.3893 (3)	0.11579 (14)	0.0487 (9)
H14A	1.1082	0.4566	0.0923	0.073*
H14B	0.9686	0.3530	0.0893	0.073*
H14C	1.1148	0.3180	0.1292	0.073*
C10A	0.6906 (4)	0.9388 (3)	0.46375 (15)	0.0538 (10)
H10D	0.6436	0.9199	0.5054	0.081*
H10E	0.6339	1.0113	0.4444	0.081*
H10F	0.7996	0.9645	0.4668	0.081*
C1B	1.2375 (4)	−0.1663 (4)	0.03816 (15)	0.0552 (10)
H1B	1.2980	−0.2078	0.0058	0.066*
C3A	0.5890 (4)	0.4968 (3)	0.09050 (16)	0.0509 (10)
H3A	0.5391	0.4133	0.0955	0.061*
C2A	0.6791 (5)	0.5372 (4)	0.03509 (16)	0.0664 (12)
H2A	0.6972	0.4820	0.0002	0.080*
C2B	1.1797 (5)	−0.0390 (4)	0.03474 (16)	0.0672 (12)
H2B	1.1967	0.0176	−0.0006	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0487 (6)	0.0377 (5)	0.0438 (6)	−0.0023 (4)	0.0036 (4)	0.0015 (4)
S1B	0.0490 (6)	0.0369 (5)	0.0445 (6)	0.0052 (4)	0.0043 (5)	−0.0007 (4)
O1A	0.0253 (12)	0.0350 (13)	0.0393 (13)	0.0024 (10)	−0.0084 (10)	0.0037 (10)
O1B	0.0248 (12)	0.0365 (13)	0.0391 (13)	0.0015 (10)	−0.0088 (10)	−0.0023 (10)
N5B	0.0254 (16)	0.0296 (16)	0.0397 (17)	−0.0026 (12)	−0.0032 (13)	0.0002 (12)
N3A	0.0215 (14)	0.0230 (14)	0.0297 (15)	0.0029 (11)	−0.0055 (11)	−0.0044 (11)
N4B	0.0239 (15)	0.0239 (15)	0.0347 (16)	−0.0002 (11)	−0.0053 (12)	−0.0003 (12)
N5A	0.0294 (16)	0.0303 (16)	0.0430 (17)	0.0038 (12)	−0.0045 (13)	−0.0040 (13)
N3B	0.0248 (15)	0.0210 (14)	0.0358 (16)	−0.0019 (11)	−0.0001 (12)	0.0015 (11)
N2A	0.0237 (15)	0.0295 (15)	0.0315 (15)	0.0013 (11)	−0.0037 (12)	−0.0027 (12)
N1A	0.0221 (15)	0.0282 (15)	0.0336 (16)	0.0009 (11)	−0.0002 (12)	−0.0025 (12)
N6A	0.0259 (16)	0.0321 (16)	0.0448 (18)	0.0015 (12)	−0.0086 (13)	−0.0011 (13)
N2B	0.0245 (15)	0.0278 (15)	0.0330 (16)	−0.0005 (11)	−0.0046 (12)	0.0052 (12)
N4A	0.0184 (14)	0.0277 (15)	0.0340 (16)	0.0036 (11)	−0.0072 (12)	−0.0009 (12)
O2B	0.0436 (16)	0.0561 (16)	0.0426 (15)	0.0036 (12)	0.0006 (12)	−0.0110 (12)
N1B	0.0206 (14)	0.0328 (16)	0.0345 (16)	−0.0001 (11)	−0.0022 (12)	0.0009 (12)
C5B	0.0227 (17)	0.0366 (19)	0.037 (2)	0.0007 (14)	−0.0060 (15)	−0.0026 (14)
O2A	0.0383 (15)	0.0574 (16)	0.0461 (15)	−0.0008 (12)	0.0008 (11)	0.0168 (12)
C5A	0.0234 (18)	0.0334 (18)	0.038 (2)	0.0021 (14)	−0.0057 (15)	0.0036 (14)
C12B	0.0225 (18)	0.0286 (19)	0.0313 (19)	−0.0047 (14)	−0.0072 (15)	−0.0001 (14)
C11A	0.0214 (18)	0.0280 (18)	0.035 (2)	0.0017 (14)	−0.0130 (15)	0.0040 (15)
C7A	0.0239 (18)	0.0261 (18)	0.0299 (19)	0.0000 (14)	0.0034 (15)	−0.0006 (14)
C6B	0.0187 (16)	0.0251 (17)	0.0299 (18)	−0.0005 (13)	0.0021 (14)	−0.0019 (14)
N6B	0.0285 (16)	0.0288 (16)	0.0513 (18)	0.0008 (12)	−0.0090 (14)	0.0012 (13)
C12A	0.0221 (18)	0.0316 (19)	0.0312 (19)	0.0043 (14)	−0.0085 (15)	−0.0027 (15)
C7B	0.0256 (18)	0.0290 (19)	0.0274 (19)	0.0048 (15)	0.0000 (15)	0.0062 (14)
C4B	0.0305 (19)	0.0297 (18)	0.0293 (19)	−0.0013 (14)	−0.0093 (15)	−0.0029 (14)
C11B	0.0229 (18)	0.0284 (18)	0.035 (2)	0.0034 (14)	−0.0111 (15)	−0.0049 (15)
C13B	0.0312 (19)	0.0330 (19)	0.037 (2)	−0.0026 (15)	−0.0012 (15)	−0.0009 (15)
C15A	0.0249 (19)	0.038 (2)	0.043 (2)	−0.0021 (14)	−0.0010 (16)	0.0045 (15)
C15B	0.0288 (19)	0.0371 (19)	0.044 (2)	0.0026 (14)	−0.0045 (17)	−0.0055 (16)
C6A	0.0212 (17)	0.0270 (18)	0.0294 (18)	0.0037 (13)	0.0031 (14)	0.0029 (14)
C13A	0.0317 (19)	0.0367 (19)	0.037 (2)	0.0089 (15)	−0.0020 (16)	0.0007 (15)
C9A	0.030 (2)	0.043 (2)	0.033 (2)	0.0090 (16)	−0.0079 (16)	0.0019 (16)
C8A	0.0263 (18)	0.0294 (18)	0.040 (2)	−0.0003 (14)	−0.0047 (15)	−0.0053 (15)
C4A	0.0269 (19)	0.0319 (18)	0.037 (2)	0.0007 (14)	−0.0095 (15)	0.0024 (15)
C8B	0.0265 (18)	0.0290 (18)	0.040 (2)	0.0024 (14)	−0.0016 (15)	0.0053 (15)
C9B	0.0237 (19)	0.041 (2)	0.037 (2)	−0.0066 (15)	−0.0082 (16)	−0.0016 (16)
C14B	0.050 (2)	0.047 (2)	0.047 (2)	−0.0030 (17)	0.0114 (18)	−0.0001 (17)
C16A	0.040 (2)	0.062 (2)	0.043 (2)	−0.0109 (17)	0.0022 (18)	0.0060 (18)
C10B	0.067 (3)	0.058 (2)	0.036 (2)	−0.0100 (19)	−0.0047 (19)	0.0167 (18)
C3B	0.076 (3)	0.040 (2)	0.045 (2)	0.0105 (19)	0.001 (2)	0.0052 (18)
C1A	0.070 (3)	0.052 (2)	0.036 (2)	−0.001 (2)	0.0071 (19)	0.0037 (18)
C16B	0.043 (2)	0.061 (2)	0.044 (2)	0.0087 (18)	−0.0017 (18)	−0.0058 (18)
C14A	0.052 (2)	0.052 (2)	0.040 (2)	0.0039 (18)	0.0115 (18)	0.0018 (17)
C10A	0.060 (3)	0.064 (3)	0.037 (2)	0.0153 (19)	−0.0008 (19)	−0.0053 (18)
C1B	0.073 (3)	0.055 (3)	0.035 (2)	0.006 (2)	0.0114 (19)	−0.0080 (18)
C3A	0.074 (3)	0.035 (2)	0.043 (2)	−0.0078 (18)	0.001 (2)	−0.0055 (17)
C2A	0.102 (4)	0.062 (3)	0.035 (2)	−0.006 (2)	0.006 (2)	−0.015 (2)
C2B	0.102 (4)	0.059 (3)	0.038 (2)	0.011 (2)	0.011 (2)	0.018 (2)

Geometric parameters (Å, º) top

S1A—C1A	1.704 (3)	C13B—H12B	0.9700
S1A—C4A	1.724 (3)	C15A—C16A	1.534 (4)
S1B—C1B	1.701 (3)	C15A—H15A	0.9700
S1B—C4B	1.717 (3)	C15A—H15B	0.9700
O1A—C7A	1.218 (3)	C15B—C16B	1.526 (4)
O1B—C7B	1.219 (3)	C15B—H15C	0.9700
N5B—C12B	1.293 (3)	C15B—H15D	0.9700
N5B—N6B	1.418 (3)	C13A—C14A	1.519 (4)
N3A—N4A	1.372 (3)	C13A—H13A	0.9700
N3A—C6A	1.391 (3)	C13A—H13B	0.9700
N3A—C7A	1.407 (3)	C9A—C10A	1.490 (4)
N4B—N3B	1.374 (3)	C9A—C8A	1.523 (4)
N4B—C11B	1.376 (3)	C8A—H8A1	0.9700
N4B—C12B	1.388 (3)	C8A—H8A2	0.9700
N5A—C12A	1.300 (3)	C4A—C3A	1.347 (4)
N5A—N6A	1.414 (3)	C8B—C9B	1.520 (4)
N3B—C6B	1.387 (3)	C8B—H8B1	0.9700
N3B—C7B	1.401 (3)	C8B—H8B2	0.9700
N2A—C7A	1.355 (3)	C9B—C10B	1.486 (4)
N2A—N1A	1.404 (3)	C14B—H11A	0.9600
N2A—C8A	1.430 (3)	C14B—H11B	0.9600
N1A—C6A	1.284 (3)	C14B—H11C	0.9600
N6A—C11A	1.304 (3)	C16A—H16A	0.9600
N2B—C7B	1.356 (3)	C16A—H16B	0.9600
N2B—N1B	1.406 (3)	C16A—H16C	0.9600
N2B—C8B	1.438 (3)	C10B—H10A	0.9600
N4A—C11A	1.367 (3)	C10B—H10B	0.9600
N4A—C12A	1.386 (3)	C10B—H10C	0.9600
O2B—C9B	1.211 (3)	C3B—C2B	1.420 (4)
N1B—C6B	1.281 (3)	C3B—H3B	0.9300
C5B—C6B	1.489 (4)	C1A—C2A	1.354 (4)
C5B—C4B	1.511 (4)	C1A—H1A	0.9300
C5B—H5B1	0.9700	C16B—H16D	0.9600
C5B—H5B2	0.9700	C16B—H16E	0.9600
O2A—C9A	1.201 (3)	C16B—H16F	0.9600
C5A—C6A	1.489 (4)	C14A—H14A	0.9600
C5A—C4A	1.504 (4)	C14A—H14B	0.9600
C5A—H5A1	0.9700	C14A—H14C	0.9600
C5A—H5A2	0.9700	C10A—H10D	0.9600
C12B—C13B	1.482 (4)	C10A—H10E	0.9600
C11A—C15A	1.481 (4)	C10A—H10F	0.9600
N6B—C11B	1.300 (3)	C1B—C2B	1.352 (4)
C12A—C13A	1.485 (4)	C1B—H1B	0.9300
C4B—C3B	1.345 (4)	C3A—C2A	1.410 (4)
C11B—C15B	1.486 (4)	C3A—H3A	0.9300
C13B—C14B	1.523 (4)	C2A—H2A	0.9300
C13B—H12A	0.9700	C2B—H2B	0.9300

C1A—S1A—C4A	92.12 (16)	N3A—C6A—C5A	125.2 (2)
C1B—S1B—C4B	92.33 (16)	C12A—C13A—C14A	112.8 (2)
C12B—N5B—N6B	108.3 (2)	C12A—C13A—H13A	109.0
N4A—N3A—C6A	127.4 (2)	C14A—C13A—H13A	109.0
N4A—N3A—C7A	123.2 (2)	C12A—C13A—H13B	109.0
C6A—N3A—C7A	109.3 (2)	C14A—C13A—H13B	109.0
N3B—N4B—C11B	127.7 (2)	H13A—C13A—H13B	107.8
N3B—N4B—C12B	125.6 (2)	O2A—C9A—C10A	124.5 (3)
C11B—N4B—C12B	106.6 (2)	O2A—C9A—C8A	121.5 (3)
C12A—N5A—N6A	108.2 (2)	C10A—C9A—C8A	114.1 (3)
N4B—N3B—C6B	127.3 (2)	N2A—C8A—C9A	113.3 (2)
N4B—N3B—C7B	123.1 (2)	N2A—C8A—H8A1	108.9
C6B—N3B—C7B	109.4 (2)	C9A—C8A—H8A1	108.9
C7A—N2A—N1A	113.2 (2)	N2A—C8A—H8A2	108.9
C7A—N2A—C8A	126.8 (3)	C9A—C8A—H8A2	108.9
N1A—N2A—C8A	119.4 (2)	H8A1—C8A—H8A2	107.7
C6A—N1A—N2A	105.6 (2)	C3A—C4A—C5A	128.4 (3)
C11A—N6A—N5A	107.6 (2)	C3A—C4A—S1A	110.7 (2)
C7B—N2B—N1B	113.2 (2)	C5A—C4A—S1A	120.8 (2)
C7B—N2B—C8B	126.1 (2)	N2B—C8B—C9B	113.4 (2)
N1B—N2B—C8B	120.0 (2)	N2B—C8B—H8B1	108.9
C11A—N4A—N3A	128.0 (2)	C9B—C8B—H8B1	108.9
C11A—N4A—C12A	107.0 (2)	N2B—C8B—H8B2	108.9
N3A—N4A—C12A	125.0 (2)	C9B—C8B—H8B2	108.9
C6B—N1B—N2B	105.1 (2)	H8B1—C8B—H8B2	107.7
C6B—C5B—C4B	112.4 (2)	O2B—C9B—C10B	124.9 (3)
C6B—C5B—H5B1	109.1	O2B—C9B—C8B	121.2 (3)
C4B—C5B—H5B1	109.1	C10B—C9B—C8B	113.9 (3)
C6B—C5B—H5B2	109.1	C13B—C14B—H11A	109.5
C4B—C5B—H5B2	109.1	C13B—C14B—H11B	109.5
H5B1—C5B—H5B2	107.9	H11A—C14B—H11B	109.5
C6A—C5A—C4A	113.1 (2)	C13B—C14B—H11C	109.5
C6A—C5A—H5A1	109.0	H11A—C14B—H11C	109.5
C4A—C5A—H5A1	109.0	H11B—C14B—H11C	109.5
C6A—C5A—H5A2	109.0	C15A—C16A—H16A	109.5
C4A—C5A—H5A2	109.0	C15A—C16A—H16B	109.5
H5A1—C5A—H5A2	107.8	H16A—C16A—H16B	109.5
N5B—C12B—N4B	108.5 (2)	C15A—C16A—H16C	109.5
N5B—C12B—C13B	128.4 (3)	H16A—C16A—H16C	109.5
N4B—C12B—C13B	123.1 (2)	H16B—C16A—H16C	109.5
N6A—C11A—N4A	109.0 (3)	C9B—C10B—H10A	109.5
N6A—C11A—C15A	126.5 (3)	C9B—C10B—H10B	109.5
N4A—C11A—C15A	124.5 (3)	H10A—C10B—H10B	109.5
O1A—C7A—N2A	131.0 (3)	C9B—C10B—H10C	109.5
O1A—C7A—N3A	127.3 (3)	H10A—C10B—H10C	109.5
N2A—C7A—N3A	101.7 (2)	H10B—C10B—H10C	109.5
N1B—C6B—N3B	110.6 (2)	C4B—C3B—C2B	112.4 (3)
N1B—C6B—C5B	123.8 (3)	C4B—C3B—H3B	123.8
N3B—C6B—C5B	125.6 (3)	C2B—C3B—H3B	123.8
C11B—N6B—N5B	107.5 (2)	C2A—C1A—S1A	111.0 (3)
N5A—C12A—N4A	108.2 (2)	C2A—C1A—H1A	124.5
N5A—C12A—C13A	128.3 (3)	S1A—C1A—H1A	124.5
N4A—C12A—C13A	123.4 (3)	C15B—C16B—H16D	109.5
O1B—C7B—N2B	131.1 (3)	C15B—C16B—H16E	109.5
O1B—C7B—N3B	127.3 (3)	H16D—C16B—H16E	109.5
N2B—C7B—N3B	101.6 (3)	C15B—C16B—H16F	109.5
C3B—C4B—C5B	127.7 (3)	H16D—C16B—H16F	109.5
C3B—C4B—S1B	111.1 (2)	H16E—C16B—H16F	109.5
C5B—C4B—S1B	121.2 (2)	C13A—C14A—H14A	109.5
N6B—C11B—N4B	109.1 (3)	C13A—C14A—H14B	109.5
N6B—C11B—C15B	126.5 (3)	H14A—C14A—H14B	109.5
N4B—C11B—C15B	124.4 (3)	C13A—C14A—H14C	109.5
C12B—C13B—C14B	112.5 (2)	H14A—C14A—H14C	109.5
C12B—C13B—H12A	109.1	H14B—C14A—H14C	109.5
C14B—C13B—H12A	109.1	C9A—C10A—H10D	109.5
C12B—C13B—H12B	109.1	C9A—C10A—H10E	109.5
C14B—C13B—H12B	109.1	H10D—C10A—H10E	109.5
H12A—C13B—H12B	107.8	C9A—C10A—H10F	109.5
C11A—C15A—C16A	114.6 (2)	H10D—C10A—H10F	109.5
C11A—C15A—H15A	108.6	H10E—C10A—H10F	109.5
C16A—C15A—H15A	108.6	C2B—C1B—S1B	110.9 (3)
C11A—C15A—H15B	108.6	C2B—C1B—H1B	124.6
C16A—C15A—H15B	108.6	S1B—C1B—H1B	124.6
H15A—C15A—H15B	107.6	C4A—C3A—C2A	113.0 (3)
C11B—C15B—C16B	114.2 (2)	C4A—C3A—H3A	123.5
C11B—C15B—H15C	108.7	C2A—C3A—H3A	123.5
C16B—C15B—H15C	108.7	C1A—C2A—C3A	113.1 (3)
C11B—C15B—H15D	108.7	C1A—C2A—H2A	123.4
C16B—C15B—H15D	108.7	C3A—C2A—H2A	123.4
H15C—C15B—H15D	107.6	C1B—C2B—C3B	113.2 (3)
N1A—C6A—N3A	110.2 (3)	C1B—C2B—H2B	123.4
N1A—C6A—C5A	124.5 (3)	C3B—C2B—H2B	123.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H5B1···N5A	0.97	2.42	3.382 (4)	171
C15B—H15D···O1A	0.97	2.60	3.561 (3)	174
C5A—H5A2···N5Bⁱ	0.97	2.43	3.386 (4)	170
C8B—H8B1···O2Aⁱⁱ	0.97	2.55	3.397 (4)	147
C8A—H8A2···O2Bⁱⁱⁱ	0.97	2.55	3.413 (4)	148

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

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