Conformational isomerism in 3-(Z)-iso­butyl­idene-1-acetyl­piperazine-2,5-dione

The title compound, C₁₀H₁₄N₂O₃, (I), is a key intermediate in the synthesis of the cyclic de­hydro­peptide albonoursin, which has been found to exhibit useful biological and pharmacological properties. It crystallizes with two mol­ecules in the asymmetric unit with different conformational structures. The methyl­propyl­idene side chain is found to be in the Z configuration about the C=C double bond for both mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.188
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ...........          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C6B
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C8A
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H14 N2 O3

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

3-(Z)-isobutylidene-1-acetylpiperazine-2,5-dione

Crystal data

C10H14N2O3	Z = 4
Mr = 210.23	F(000) = 448
Triclinic, P1	Dx = 1.271 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.7310 (18) Å	Cell parameters from 25 reflections
b = 10.827 (3) Å	θ = 19.4–20.0°
c = 9.7916 (14) Å	µ = 0.10 mm^−1
α = 95.607 (17)°	T = 295 K
β = 94.680 (13)°	Prism, colorless
γ = 76.484 (17)°	0.60 × 0.50 × 0.30 mm
V = 1098.8 (4) Å^3

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.019
Radiation source: Rigaku rotating anode	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = 0→12
ω–2/q scans	k = −12→12
4100 measured reflections	l = −11→11
3872 independent reflections	3 standard reflections every 150 reflections
2691 reflections with I > 2σ(I)	intensity decay: 1.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.188	w = 1/[σ^2(Fo^2) + (0.1241P)^2 + 0.0666P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3872 reflections	Δρmax = 0.26 e Å^−3
272 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (7)

Special details

Experimental. The scan width was (0.94 + 0.35tanθ)° with an ω scan speed of 32° per minute (up to 4 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.4705 (2)	1.1121 (3)	0.65742 (19)	0.0950 (9)
O2A	−0.50782 (14)	1.16131 (16)	1.06862 (16)	0.0551 (5)
O3A	−0.06617 (14)	0.93690 (16)	0.84666 (15)	0.0542 (5)
N1A	−0.39717 (15)	1.08414 (16)	0.87646 (16)	0.0426 (5)
N2A	−0.17284 (15)	1.02245 (17)	1.03568 (17)	0.0432 (5)
C1A	−0.5803 (2)	1.2652 (3)	0.8219 (3)	0.0649 (9)
C2A	−0.4828 (2)	1.1500 (3)	0.7771 (2)	0.0568 (8)
C3A	−0.40915 (19)	1.10772 (19)	1.0179 (2)	0.0416 (6)
C4A	−0.28794 (18)	1.06084 (19)	1.1038 (2)	0.0410 (6)
C5A	−0.16766 (19)	0.97793 (19)	0.9037 (2)	0.0412 (6)
C6A	−0.2940 (2)	0.9796 (2)	0.8266 (2)	0.0499 (7)
C7A	−0.2932 (2)	1.0650 (2)	1.2397 (2)	0.0528 (8)
C8A	−0.1856 (2)	1.0277 (3)	1.3461 (2)	0.0621 (9)
C9A	−0.1983 (3)	0.9084 (4)	1.4082 (4)	0.0966 (14)
C10A	−0.1891 (4)	1.1344 (4)	1.4587 (3)	0.1017 (16)
O1B	0.27152 (19)	0.6690 (2)	1.0294 (2)	0.0761 (8)
O2B	−0.10745 (18)	0.6827 (2)	1.03789 (17)	0.0773 (7)
O3B	0.1411 (2)	0.5160 (3)	0.5831 (2)	0.1056 (12)
N1B	0.08118 (18)	0.64005 (17)	0.93396 (18)	0.0485 (6)
N2B	−0.04459 (19)	0.5660 (2)	0.68861 (19)	0.0587 (7)
C1B	0.1027 (3)	0.7346 (3)	1.1785 (3)	0.0710 (10)
C2B	0.1584 (3)	0.6803 (2)	1.0460 (2)	0.0543 (8)
C3B	−0.0487 (2)	0.6465 (2)	0.9352 (2)	0.0497 (7)
C4B	−0.1169 (2)	0.6072 (2)	0.8047 (2)	0.0459 (7)
C5B	0.0812 (3)	0.5543 (3)	0.6859 (3)	0.0671 (10)
C6B	0.1543 (3)	0.5876 (3)	0.8142 (3)	0.0766 (10)
C7B	−0.2415 (2)	0.6115 (2)	0.8017 (2)	0.0490 (7)
C8B	−0.3269 (2)	0.5779 (2)	0.6809 (2)	0.0532 (8)
C9B	−0.4407 (3)	0.5375 (3)	0.7275 (3)	0.0796 (11)
C10B	−0.3714 (3)	0.6906 (3)	0.5929 (3)	0.0716 (10)
H1A	−0.61340	1.31250	0.74500	0.0780*
H2A	−0.64820	1.24040	0.86050	0.0780*
H3A	−0.54170	1.31650	0.88890	0.0780*
H4A	−0.10300	1.02790	1.08090	0.0520*
H5A	−0.31700	0.90130	0.83560	0.0600*
H6A	−0.28510	0.98780	0.73240	0.0600*
H7A	−0.37610	1.09560	1.27370	0.0630*
H8A	−0.10600	1.01110	1.30400	0.0750*
H9A	−0.19180	0.84000	1.33850	0.1160*
H10A	−0.13180	0.88690	1.47780	0.1160*
H11A	−0.27940	0.92350	1.44700	0.1160*
H12A	−0.18720	1.21070	1.41950	0.1220*
H13A	−0.26560	1.14670	1.50580	0.1220*
H14A	−0.11680	1.11270	1.52170	0.1220*
H1B	0.16510	0.76660	1.23680	0.0850*
H2B	0.07740	0.67010	1.22130	0.0850*
H3B	0.03000	0.80190	1.16210	0.0850*
H4B	−0.08470	0.54700	0.61400	0.0700*
H5B	0.19950	0.64870	0.79420	0.0920*
H6B	0.21400	0.51220	0.83860	0.0920*
H7B	−0.28170	0.63890	0.88570	0.0590*
H8B	−0.27850	0.50860	0.62630	0.0640*
H9B	−0.41180	0.47240	0.78870	0.0960*
H10B	−0.49550	0.60860	0.77320	0.0960*
H11B	−0.48660	0.50600	0.64990	0.0960*
H12B	−0.29950	0.70770	0.55430	0.0860*
H13B	−0.43050	0.67080	0.52120	0.0860*
H14B	−0.41210	0.76350	0.64840	0.0860*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0772 (14)	0.144 (2)	0.0439 (11)	0.0132 (13)	−0.0015 (9)	0.0080 (11)
O2A	0.0354 (8)	0.0741 (11)	0.0514 (9)	0.0001 (7)	0.0110 (7)	0.0072 (7)
O3A	0.0367 (8)	0.0728 (10)	0.0501 (9)	−0.0076 (7)	0.0109 (7)	−0.0046 (7)
N1A	0.0348 (9)	0.0531 (10)	0.0395 (9)	−0.0094 (8)	0.0034 (7)	0.0027 (7)
N2A	0.0320 (9)	0.0583 (10)	0.0389 (9)	−0.0087 (7)	0.0041 (7)	0.0037 (7)
C1A	0.0526 (14)	0.0752 (17)	0.0631 (16)	−0.0016 (12)	0.0015 (11)	0.0199 (12)
C2A	0.0450 (13)	0.0803 (16)	0.0461 (13)	−0.0133 (11)	0.0015 (10)	0.0128 (11)
C3A	0.0362 (11)	0.0471 (11)	0.0433 (11)	−0.0116 (9)	0.0057 (9)	0.0041 (9)
C4A	0.0329 (10)	0.0508 (11)	0.0397 (11)	−0.0091 (9)	0.0071 (8)	0.0026 (8)
C5A	0.0359 (10)	0.0460 (11)	0.0423 (11)	−0.0087 (8)	0.0085 (8)	0.0035 (8)
C6A	0.0385 (11)	0.0639 (14)	0.0454 (12)	−0.0105 (10)	0.0083 (9)	−0.0073 (10)
C7A	0.0407 (12)	0.0752 (15)	0.0439 (12)	−0.0132 (11)	0.0088 (9)	0.0058 (10)
C8A	0.0433 (12)	0.105 (2)	0.0389 (12)	−0.0173 (13)	0.0039 (9)	0.0086 (12)
C9A	0.082 (2)	0.129 (3)	0.085 (2)	−0.029 (2)	−0.0201 (17)	0.048 (2)
C10A	0.100 (3)	0.136 (3)	0.067 (2)	−0.036 (2)	−0.0119 (17)	−0.010 (2)
O1B	0.0662 (13)	0.0950 (14)	0.0720 (12)	−0.0327 (11)	−0.0070 (9)	0.0053 (10)
O2B	0.0663 (12)	0.1188 (16)	0.0456 (10)	−0.0253 (11)	0.0157 (8)	−0.0194 (10)
O3B	0.0697 (13)	0.183 (3)	0.0635 (13)	−0.0428 (15)	0.0278 (10)	−0.0472 (14)
N1B	0.0502 (11)	0.0500 (10)	0.0433 (10)	−0.0093 (8)	0.0028 (8)	−0.0007 (8)
N2B	0.0510 (12)	0.0822 (14)	0.0423 (10)	−0.0185 (10)	0.0101 (8)	−0.0126 (9)
C1B	0.0833 (19)	0.0670 (16)	0.0572 (15)	−0.0161 (14)	−0.0073 (13)	−0.0099 (12)
C2B	0.0655 (16)	0.0424 (12)	0.0545 (13)	−0.0133 (11)	−0.0073 (11)	0.0078 (10)
C3B	0.0569 (14)	0.0492 (12)	0.0415 (11)	−0.0088 (10)	0.0065 (10)	0.0021 (9)
C4B	0.0504 (13)	0.0463 (12)	0.0406 (11)	−0.0092 (9)	0.0093 (9)	−0.0001 (9)
C5B	0.0592 (16)	0.0903 (19)	0.0521 (14)	−0.0217 (14)	0.0160 (12)	−0.0149 (13)
C6B	0.0601 (16)	0.116 (2)	0.0531 (15)	−0.0240 (16)	0.0095 (12)	−0.0106 (15)
C7B	0.0542 (14)	0.0499 (12)	0.0421 (11)	−0.0099 (10)	0.0073 (9)	0.0010 (9)
C8B	0.0560 (14)	0.0558 (13)	0.0477 (12)	−0.0146 (11)	0.0038 (10)	−0.0008 (10)
C9B	0.0728 (19)	0.103 (2)	0.0740 (18)	−0.0428 (17)	−0.0043 (14)	0.0123 (16)
C10B	0.0842 (19)	0.0764 (17)	0.0538 (15)	−0.0197 (15)	−0.0077 (13)	0.0100 (13)

Geometric parameters (Å, º)

O1A—C2A	1.210 (3)	O1B—C2B	1.214 (4)
O2A—C3A	1.203 (3)	O2B—C3B	1.214 (3)
O3A—C5A	1.233 (3)	O3B—C5B	1.224 (4)
N1A—C2A	1.408 (3)	N1B—C6B	1.458 (4)
N1A—C3A	1.394 (3)	N1B—C2B	1.417 (3)
N1A—C6A	1.463 (3)	N1B—C3B	1.380 (3)
N2A—C4A	1.408 (3)	N2B—C5B	1.328 (4)
N2A—C5A	1.335 (3)	N2B—C4B	1.406 (3)
N2A—H4A	0.8501	N2B—H4B	0.8497
C1A—C2A	1.484 (4)	C1B—C2B	1.483 (4)
C3A—C4A	1.501 (3)	C3B—C4B	1.495 (3)
C4A—C7A	1.332 (3)	C4B—C7B	1.325 (3)
C5A—C6A	1.494 (3)	C5B—C6B	1.485 (4)
C7A—C8A	1.500 (3)	C7B—C8B	1.505 (3)
C8A—C10A	1.513 (4)	C8B—C9B	1.507 (4)
C8A—C9A	1.519 (5)	C8B—C10B	1.525 (4)
C1A—H2A	0.9498	C1B—H1B	0.9496
C1A—H3A	0.9500	C1B—H2B	0.9494
C1A—H1A	0.9498	C1B—H3B	0.9498
C6A—H6A	0.9498	C6B—H5B	0.9498
C6A—H5A	0.9504	C6B—H6B	0.9501
C7A—H7A	0.9492	C7B—H7B	0.9492
C8A—H8A	0.9503	C8B—H8B	0.9504
C9A—H10A	0.9497	C9B—H9B	0.9498
C9A—H11A	0.9507	C9B—H10B	0.9501
C9A—H9A	0.9508	C9B—H11B	0.9503
C10A—H14A	0.9501	C10B—H12B	0.9489
C10A—H12A	0.9494	C10B—H13B	0.9500
C10A—H13A	0.9503	C10B—H14B	0.9502
O1B···C3A^i	3.200 (3)	C4A···H5A	3.0347
O1B···C4A^i	3.363 (3)	C4B···H2B^v	2.9209
O2A···N1A^ii	3.166 (3)	C5A···H4A^i	2.8822
O2A···C1A	2.743 (3)	C5B···H4B^iii	3.0326
O2A···C3A^ii	3.256 (3)	C7B···H5A	3.0436
O2A···C6A^ii	3.175 (3)	C8A···H4A	2.8118
O2B···C1B	2.689 (4)	C8B···H4B	2.6692
O3A···C3B	3.302 (3)	C10A···H1B^vii	3.0796
O3A···N2A^i	2.836 (2)	H1B···C10A^vii	3.0796
O3B···C8B^iii	3.327 (3)	H2A···C3A	3.0140
O3B···N2B^iii	2.908 (3)	H2A···O2A	2.5283
O3B···C10B^iii	3.382 (4)	H2A···O2B^ii	2.7932
O1A···H11A^ii	2.8906	H2B···N2B^v	2.8894
O1A···H6A	2.2387	H2B···C3B	3.0244
O1A···H13A^iv	2.8645	H2B···C4B^v	2.9209
O1B···H6B	2.5368	H2B···O2B	2.5532
O1B···H9B^v	2.6077	H3A···O2A	2.4980
O1B···H5B	2.3747	H3A···C3A	2.7368
O2A···H7B^ii	2.7700	H3B···O2B	2.3687
O2A···H2A	2.5283	H3B···C3B	2.8474
O2A···H5A^ii	2.4250	H4A···C5A^i	2.8822
O2A···H3A	2.4980	H4A···O3A^i	2.0011
O2A···H7A	2.4254	H4A···H8A	2.2132
O2A···H10B^ii	2.8080	H4A···C8A	2.8118
O2B···H2B	2.5532	H4B···C5B^iii	3.0326
O2B···H7B	2.4008	H4B···O3B^iii	2.0740
O2B···H2A^ii	2.7932	H4B···H8B	2.2287
O2B···H3B	2.3687	H4B···C8B	2.6692
O3A···H4A^i	2.0011	H5A···C4A	3.0347
O3A···H8A^i	2.6457	H5A···O2A^ii	2.4250
O3B···H8B^iii	2.5791	H5A···H14B	2.5494
O3B···H12B^iii	2.8944	H5A···C7B	3.0436
O3B···H4B^iii	2.0740	H5B···O1B	2.3747
N1A···O2A^ii	3.166 (3)	H6A···O1A	2.2387
N1A···N2A	2.741 (2)	H6B···C1A^viii	3.0439
N1B···N2B	2.799 (3)	H6B···O1B	2.5368
N2A···O3A^i	2.836 (2)	H7A···H14B^ii	2.5514
N2A···C2B^i	3.432 (3)	H7A···O2A	2.4254
N2A···N1A	2.741 (2)	H7A···H13A	2.5492
N2B···O3B^iii	2.908 (3)	H7B···O2A^ii	2.7700
N2B···N1B	2.799 (3)	H7B···H9B	2.5935
N2A···H8A	2.6733	H7B···H10B	2.5404
N2B···H2B^v	2.8894	H7B···O2B	2.4008
N2B···H8B	2.7321	H8A···O3A^i	2.6457
C1A···O2A	2.743 (3)	H8A···H4A	2.2132
C1B···C5A^i	3.524 (4)	H8A···N2A	2.6733
C1B···O2B	2.689 (4)	H8B···N2B	2.7321
C2B···C7B^v	3.520 (3)	H8B···O3B^iii	2.5791
C2B···N2A^i	3.432 (3)	H8B···H4B	2.2287
C3A···O1B^i	3.200 (3)	H9B···O1B^v	2.6077
C3A···O2A^ii	3.256 (3)	H9B···H7B	2.5935
C3A···C3A^ii	3.350 (3)	H10A···H14A	2.4809
C3B···C5A	3.551 (3)	H10B···H14B	2.5273
C3B···C3B^v	3.433 (3)	H10B···O2A^ii	2.8080
C3B···O3A	3.302 (3)	H10B···H7B	2.5404
C4A···O1B^i	3.363 (3)	H11A···H13A	2.4647
C5A···C1B^i	3.524 (4)	H11A···O1A^ii	2.8906
C5A···C3B	3.551 (3)	H11B···H13B	2.4899
C6A···O2A^ii	3.175 (3)	H12B···O3B^iii	2.8944
C7B···C2B^v	3.520 (3)	H13A···O1A^ix	2.8645
C8B···O3B^iii	3.327 (3)	H13A···H7A	2.5492
C10B···O3B^iii	3.382 (4)	H13A···H11A	2.4647
C1A···H6B^vi	3.0439	H13B···H11B	2.4899
C3A···H3A	2.7368	H14A···H10A	2.4809
C3A···H2A	3.0140	H14B···H5A	2.5494
C3B···H3B	2.8474	H14B···H10B	2.5273
C3B···H2B	3.0244	H14B···H7A^ii	2.5514
C2A—N1A—C3A	124.14 (18)	H12A—C10A—H13A	109.44
C2A—N1A—C6A	117.28 (17)	H12A—C10A—H14A	109.54
C3A—N1A—C6A	118.47 (16)	C8A—C10A—H13A	109.47
C4A—N2A—C5A	123.42 (17)	C8A—C10A—H14A	109.46
C5A—N2A—H4A	118.25	C8A—C10A—H12A	109.52
C4A—N2A—H4A	118.32	H13A—C10A—H14A	109.39
O1A—C2A—N1A	118.1 (3)	O1B—C2B—N1B	117.6 (2)
O1A—C2A—C1A	122.7 (3)	O1B—C2B—C1B	121.3 (2)
N1A—C2A—C1A	119.22 (19)	N1B—C2B—C1B	121.1 (3)
N1A—C3A—C4A	114.57 (17)	N1B—C3B—C4B	117.91 (18)
O2A—C3A—N1A	123.49 (19)	O2B—C3B—N1B	122.0 (2)
O2A—C3A—C4A	121.94 (18)	O2B—C3B—C4B	120.1 (2)
N2A—C4A—C3A	117.33 (17)	N2B—C4B—C3B	117.90 (19)
N2A—C4A—C7A	123.57 (19)	N2B—C4B—C7B	122.30 (19)
C3A—C4A—C7A	118.96 (19)	C3B—C4B—C7B	119.80 (19)
O3A—C5A—N2A	123.26 (19)	O3B—C5B—N2B	123.4 (3)
N2A—C5A—C6A	115.91 (18)	N2B—C5B—C6B	118.8 (3)
O3A—C5A—C6A	120.83 (18)	O3B—C5B—C6B	117.8 (3)
N1A—C6A—C5A	113.11 (17)	N1B—C6B—C5B	117.3 (3)
C4A—C7A—C8A	128.6 (2)	C4B—C7B—C8B	127.71 (19)
C7A—C8A—C9A	109.8 (2)	C7B—C8B—C9B	111.14 (19)
C7A—C8A—C10A	110.1 (3)	C7B—C8B—C10B	110.18 (19)
C9A—C8A—C10A	109.3 (2)	C9B—C8B—C10B	110.4 (2)
C2A—C1A—H3A	109.46	C2B—C1B—H1B	109.41
H2A—C1A—H3A	109.46	C2B—C1B—H2B	109.47
C2A—C1A—H2A	109.50	C2B—C1B—H3B	109.45
C2A—C1A—H1A	109.47	H1B—C1B—H2B	109.52
H1A—C1A—H2A	109.47	H1B—C1B—H3B	109.49
H1A—C1A—H3A	109.47	H2B—C1B—H3B	109.49
H5A—C6A—H6A	109.45	N1B—C6B—H5B	107.46
N1A—C6A—H5A	108.48	N1B—C6B—H6B	107.53
N1A—C6A—H6A	108.58	C5B—C6B—H5B	107.48
C5A—C6A—H5A	108.57	C5B—C6B—H6B	107.46
C5A—C6A—H6A	108.60	H5B—C6B—H6B	109.41
C4A—C7A—H7A	115.68	C4B—C7B—H7B	116.18
C8A—C7A—H7A	115.69	C8B—C7B—H7B	116.11
C10A—C8A—H8A	109.26	C7B—C8B—H8B	108.35
C7A—C8A—H8A	109.19	C9B—C8B—H8B	108.35
C9A—C8A—H8A	109.23	C10B—C8B—H8B	108.29
C8A—C9A—H10A	109.52	C8B—C9B—H9B	109.50
H9A—C9A—H11A	109.38	C8B—C9B—H10B	109.47
C8A—C9A—H9A	109.48	C8B—C9B—H11B	109.46
H10A—C9A—H11A	109.51	H9B—C9B—H10B	109.48
H9A—C9A—H10A	109.45	H9B—C9B—H11B	109.43
C8A—C9A—H11A	109.49	H10B—C9B—H11B	109.48
C2B—N1B—C3B	125.08 (19)	C8B—C10B—H12B	109.49
C2B—N1B—C6B	112.6 (2)	C8B—C10B—H13B	109.47
C3B—N1B—C6B	122.3 (2)	C8B—C10B—H14B	109.47
C4B—N2B—C5B	125.4 (2)	H12B—C10B—H13B	109.46
C5B—N2B—H4B	117.31	H12B—C10B—H14B	109.51
C4B—N2B—H4B	117.28	H13B—C10B—H14B	109.43
C3A—N1A—C2A—O1A	−172.2 (2)	C4B—N2B—C5B—C6B	−0.5 (4)
C3A—N1A—C2A—C1A	10.2 (3)	C4B—N2B—C5B—O3B	178.7 (3)
C6A—N1A—C2A—O1A	4.0 (3)	C5B—N2B—C4B—C3B	2.7 (4)
C6A—N1A—C2A—C1A	−173.5 (2)	C5B—N2B—C4B—C7B	−177.0 (3)
C2A—N1A—C3A—O2A	19.7 (3)	N1A—C3A—C4A—N2A	12.1 (3)
C2A—N1A—C3A—C4A	−160.2 (2)	O2A—C3A—C4A—C7A	8.1 (3)
C6A—N1A—C3A—O2A	−156.5 (2)	N1A—C3A—C4A—C7A	−171.97 (19)
C6A—N1A—C3A—C4A	23.6 (3)	O2A—C3A—C4A—N2A	−167.8 (2)
C2A—N1A—C6A—C5A	137.8 (2)	C3A—C4A—C7A—C8A	−178.0 (2)
C3A—N1A—C6A—C5A	−45.7 (2)	N2A—C4A—C7A—C8A	−2.4 (4)
C5A—N2A—C4A—C3A	−27.2 (3)	N2A—C5A—C6A—N1A	30.9 (3)
C5A—N2A—C4A—C7A	157.1 (2)	O3A—C5A—C6A—N1A	−149.42 (19)
C4A—N2A—C5A—O3A	−175.3 (2)	C4A—C7A—C8A—C9A	−110.8 (3)
C4A—N2A—C5A—C6A	4.4 (3)	C4A—C7A—C8A—C10A	128.8 (3)
C6B—N1B—C2B—O1B	1.2 (3)	O2B—C3B—C4B—N2B	180.0 (2)
C6B—N1B—C2B—C1B	−179.0 (2)	O2B—C3B—C4B—C7B	−0.3 (3)
C3B—N1B—C2B—O1B	−179.8 (2)	N1B—C3B—C4B—C7B	179.7 (2)
C2B—N1B—C3B—O2B	−3.7 (3)	N1B—C3B—C4B—N2B	0.0 (3)
C2B—N1B—C3B—C4B	176.26 (19)	C3B—C4B—C7B—C8B	179.1 (2)
C2B—N1B—C6B—C5B	−174.0 (2)	N2B—C4B—C7B—C8B	−1.2 (4)
C3B—N1B—C2B—C1B	0.0 (3)	O3B—C5B—C6B—N1B	176.6 (3)
C3B—N1B—C6B—C5B	6.9 (4)	N2B—C5B—C6B—N1B	−4.2 (4)
C6B—N1B—C3B—O2B	175.2 (2)	C4B—C7B—C8B—C9B	154.1 (2)
C6B—N1B—C3B—C4B	−4.8 (3)	C4B—C7B—C8B—C10B	−83.1 (3)

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x−1, −y+2, −z+2; (iii) −x, −y+1, −z+1; (iv) x, y, z−1; (v) −x, −y+1, −z+2; (vi) x−1, y+1, z; (vii) −x, −y+2, −z+3; (viii) x+1, y−1, z; (ix) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H4A···O3A^i	0.85	2.00	2.836 (2)	167
N2B—H4B···O3B^iii	0.85	2.07	2.908 (3)	167
C6A—H5A···O2A^ii	0.95	2.42	3.175 (3)	136
C6A—H6A···O1A	0.95	2.24	2.659 (3)	106
C7A—H7A···O2A	0.95	2.43	2.790 (3)	103
C7B—H7B···O2B	0.95	2.40	2.764 (3)	102
C8B—H8B···O3B^iii	0.95	2.58	3.327 (3)	136

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x−1, −y+2, −z+2; (iii) −x, −y+1, −z+1.