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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023729/rn6001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023729/rn6001Isup2.hkl
Contains datablock I

CCDC reference: 227018

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

Computing details top

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 top
Crystal data top
C10H14N2O3Z = 4
Mr = 210.23F(000) = 448
Triclinic, P1Dx = 1.271 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 10.7310 (18) ÅCell parameters from 25 reflections
b = 10.827 (3) Åθ = 19.4–20.0°
c = 9.7916 (14) ŵ = 0.10 mm1
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) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.019
Radiation source: Rigaku rotating anodeθmax = 25.0°, θmin = 2.1°
Graphite monochromatorh = 012
ω–2/q scansk = 1212
4100 measured reflectionsl = 1111
3872 independent reflections3 standard reflections every 150 reflections
2691 reflections with I > 2σ(I) intensity decay: 1.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.188 w = 1/[σ2(Fo2) + (0.1241P)2 + 0.0666P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3872 reflectionsΔρmax = 0.26 e Å3
272 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (7)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O1A0.4705 (2)1.1121 (3)0.65742 (19)0.0950 (9)
O2A0.50782 (14)1.16131 (16)1.06862 (16)0.0551 (5)
O3A0.06617 (14)0.93690 (16)0.84666 (15)0.0542 (5)
N1A0.39717 (15)1.08414 (16)0.87646 (16)0.0426 (5)
N2A0.17284 (15)1.02245 (17)1.03568 (17)0.0432 (5)
C1A0.5803 (2)1.2652 (3)0.8219 (3)0.0649 (9)
C2A0.4828 (2)1.1500 (3)0.7771 (2)0.0568 (8)
C3A0.40915 (19)1.10772 (19)1.0179 (2)0.0416 (6)
C4A0.28794 (18)1.06084 (19)1.1038 (2)0.0410 (6)
C5A0.16766 (19)0.97793 (19)0.9037 (2)0.0412 (6)
C6A0.2940 (2)0.9796 (2)0.8266 (2)0.0499 (7)
C7A0.2932 (2)1.0650 (2)1.2397 (2)0.0528 (8)
C8A0.1856 (2)1.0277 (3)1.3461 (2)0.0621 (9)
C9A0.1983 (3)0.9084 (4)1.4082 (4)0.0966 (14)
C10A0.1891 (4)1.1344 (4)1.4587 (3)0.1017 (16)
O1B0.27152 (19)0.6690 (2)1.0294 (2)0.0761 (8)
O2B0.10745 (18)0.6827 (2)1.03789 (17)0.0773 (7)
O3B0.1411 (2)0.5160 (3)0.5831 (2)0.1056 (12)
N1B0.08118 (18)0.64005 (17)0.93396 (18)0.0485 (6)
N2B0.04459 (19)0.5660 (2)0.68861 (19)0.0587 (7)
C1B0.1027 (3)0.7346 (3)1.1785 (3)0.0710 (10)
C2B0.1584 (3)0.6803 (2)1.0460 (2)0.0543 (8)
C3B0.0487 (2)0.6465 (2)0.9352 (2)0.0497 (7)
C4B0.1169 (2)0.6072 (2)0.8047 (2)0.0459 (7)
C5B0.0812 (3)0.5543 (3)0.6859 (3)0.0671 (10)
C6B0.1543 (3)0.5876 (3)0.8142 (3)0.0766 (10)
C7B0.2415 (2)0.6115 (2)0.8017 (2)0.0490 (7)
C8B0.3269 (2)0.5779 (2)0.6809 (2)0.0532 (8)
C9B0.4407 (3)0.5375 (3)0.7275 (3)0.0796 (11)
C10B0.3714 (3)0.6906 (3)0.5929 (3)0.0716 (10)
H1A0.613401.312500.745000.0780*
H2A0.648201.240400.860500.0780*
H3A0.541701.316500.888900.0780*
H4A0.103001.027901.080900.0520*
H5A0.317000.901300.835600.0600*
H6A0.285100.987800.732400.0600*
H7A0.376101.095601.273700.0630*
H8A0.106001.011101.304000.0750*
H9A0.191800.840001.338500.1160*
H10A0.131800.886901.477800.1160*
H11A0.279400.923501.447000.1160*
H12A0.187201.210701.419500.1220*
H13A0.265601.146701.505800.1220*
H14A0.116801.112701.521700.1220*
H1B0.165100.766601.236800.0850*
H2B0.077400.670101.221300.0850*
H3B0.030000.801901.162100.0850*
H4B0.084700.547000.614000.0700*
H5B0.199500.648700.794200.0920*
H6B0.214000.512200.838600.0920*
H7B0.281700.638900.885700.0590*
H8B0.278500.508600.626300.0640*
H9B0.411800.472400.788700.0960*
H10B0.495500.608600.773200.0960*
H11B0.486600.506000.649900.0960*
H12B0.299500.707700.554300.0860*
H13B0.430500.670800.521200.0860*
H14B0.412100.763500.648400.0860*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0772 (14)0.144 (2)0.0439 (11)0.0132 (13)0.0015 (9)0.0080 (11)
O2A0.0354 (8)0.0741 (11)0.0514 (9)0.0001 (7)0.0110 (7)0.0072 (7)
O3A0.0367 (8)0.0728 (10)0.0501 (9)0.0076 (7)0.0109 (7)0.0046 (7)
N1A0.0348 (9)0.0531 (10)0.0395 (9)0.0094 (8)0.0034 (7)0.0027 (7)
N2A0.0320 (9)0.0583 (10)0.0389 (9)0.0087 (7)0.0041 (7)0.0037 (7)
C1A0.0526 (14)0.0752 (17)0.0631 (16)0.0016 (12)0.0015 (11)0.0199 (12)
C2A0.0450 (13)0.0803 (16)0.0461 (13)0.0133 (11)0.0015 (10)0.0128 (11)
C3A0.0362 (11)0.0471 (11)0.0433 (11)0.0116 (9)0.0057 (9)0.0041 (9)
C4A0.0329 (10)0.0508 (11)0.0397 (11)0.0091 (9)0.0071 (8)0.0026 (8)
C5A0.0359 (10)0.0460 (11)0.0423 (11)0.0087 (8)0.0085 (8)0.0035 (8)
C6A0.0385 (11)0.0639 (14)0.0454 (12)0.0105 (10)0.0083 (9)0.0073 (10)
C7A0.0407 (12)0.0752 (15)0.0439 (12)0.0132 (11)0.0088 (9)0.0058 (10)
C8A0.0433 (12)0.105 (2)0.0389 (12)0.0173 (13)0.0039 (9)0.0086 (12)
C9A0.082 (2)0.129 (3)0.085 (2)0.029 (2)0.0201 (17)0.048 (2)
C10A0.100 (3)0.136 (3)0.067 (2)0.036 (2)0.0119 (17)0.010 (2)
O1B0.0662 (13)0.0950 (14)0.0720 (12)0.0327 (11)0.0070 (9)0.0053 (10)
O2B0.0663 (12)0.1188 (16)0.0456 (10)0.0253 (11)0.0157 (8)0.0194 (10)
O3B0.0697 (13)0.183 (3)0.0635 (13)0.0428 (15)0.0278 (10)0.0472 (14)
N1B0.0502 (11)0.0500 (10)0.0433 (10)0.0093 (8)0.0028 (8)0.0007 (8)
N2B0.0510 (12)0.0822 (14)0.0423 (10)0.0185 (10)0.0101 (8)0.0126 (9)
C1B0.0833 (19)0.0670 (16)0.0572 (15)0.0161 (14)0.0073 (13)0.0099 (12)
C2B0.0655 (16)0.0424 (12)0.0545 (13)0.0133 (11)0.0073 (11)0.0078 (10)
C3B0.0569 (14)0.0492 (12)0.0415 (11)0.0088 (10)0.0065 (10)0.0021 (9)
C4B0.0504 (13)0.0463 (12)0.0406 (11)0.0092 (9)0.0093 (9)0.0001 (9)
C5B0.0592 (16)0.0903 (19)0.0521 (14)0.0217 (14)0.0160 (12)0.0149 (13)
C6B0.0601 (16)0.116 (2)0.0531 (15)0.0240 (16)0.0095 (12)0.0106 (15)
C7B0.0542 (14)0.0499 (12)0.0421 (11)0.0099 (10)0.0073 (9)0.0010 (9)
C8B0.0560 (14)0.0558 (13)0.0477 (12)0.0146 (11)0.0038 (10)0.0008 (10)
C9B0.0728 (19)0.103 (2)0.0740 (18)0.0428 (17)0.0043 (14)0.0123 (16)
C10B0.0842 (19)0.0764 (17)0.0538 (15)0.0197 (15)0.0077 (13)0.0100 (13)
Geometric parameters (Å, º) top
O1A—C2A1.210 (3)O1B—C2B1.214 (4)
O2A—C3A1.203 (3)O2B—C3B1.214 (3)
O3A—C5A1.233 (3)O3B—C5B1.224 (4)
N1A—C2A1.408 (3)N1B—C6B1.458 (4)
N1A—C3A1.394 (3)N1B—C2B1.417 (3)
N1A—C6A1.463 (3)N1B—C3B1.380 (3)
N2A—C4A1.408 (3)N2B—C5B1.328 (4)
N2A—C5A1.335 (3)N2B—C4B1.406 (3)
N2A—H4A0.8501N2B—H4B0.8497
C1A—C2A1.484 (4)C1B—C2B1.483 (4)
C3A—C4A1.501 (3)C3B—C4B1.495 (3)
C4A—C7A1.332 (3)C4B—C7B1.325 (3)
C5A—C6A1.494 (3)C5B—C6B1.485 (4)
C7A—C8A1.500 (3)C7B—C8B1.505 (3)
C8A—C10A1.513 (4)C8B—C9B1.507 (4)
C8A—C9A1.519 (5)C8B—C10B1.525 (4)
C1A—H2A0.9498C1B—H1B0.9496
C1A—H3A0.9500C1B—H2B0.9494
C1A—H1A0.9498C1B—H3B0.9498
C6A—H6A0.9498C6B—H5B0.9498
C6A—H5A0.9504C6B—H6B0.9501
C7A—H7A0.9492C7B—H7B0.9492
C8A—H8A0.9503C8B—H8B0.9504
C9A—H10A0.9497C9B—H9B0.9498
C9A—H11A0.9507C9B—H10B0.9501
C9A—H9A0.9508C9B—H11B0.9503
C10A—H14A0.9501C10B—H12B0.9489
C10A—H12A0.9494C10B—H13B0.9500
C10A—H13A0.9503C10B—H14B0.9502
O1B···C3Ai3.200 (3)C4A···H5A3.0347
O1B···C4Ai3.363 (3)C4B···H2Bv2.9209
O2A···N1Aii3.166 (3)C5A···H4Ai2.8822
O2A···C1A2.743 (3)C5B···H4Biii3.0326
O2A···C3Aii3.256 (3)C7B···H5A3.0436
O2A···C6Aii3.175 (3)C8A···H4A2.8118
O2B···C1B2.689 (4)C8B···H4B2.6692
O3A···C3B3.302 (3)C10A···H1Bvii3.0796
O3A···N2Ai2.836 (2)H1B···C10Avii3.0796
O3B···C8Biii3.327 (3)H2A···C3A3.0140
O3B···N2Biii2.908 (3)H2A···O2A2.5283
O3B···C10Biii3.382 (4)H2A···O2Bii2.7932
O1A···H11Aii2.8906H2B···N2Bv2.8894
O1A···H6A2.2387H2B···C3B3.0244
O1A···H13Aiv2.8645H2B···C4Bv2.9209
O1B···H6B2.5368H2B···O2B2.5532
O1B···H9Bv2.6077H3A···O2A2.4980
O1B···H5B2.3747H3A···C3A2.7368
O2A···H7Bii2.7700H3B···O2B2.3687
O2A···H2A2.5283H3B···C3B2.8474
O2A···H5Aii2.4250H4A···C5Ai2.8822
O2A···H3A2.4980H4A···O3Ai2.0011
O2A···H7A2.4254H4A···H8A2.2132
O2A···H10Bii2.8080H4A···C8A2.8118
O2B···H2B2.5532H4B···C5Biii3.0326
O2B···H7B2.4008H4B···O3Biii2.0740
O2B···H2Aii2.7932H4B···H8B2.2287
O2B···H3B2.3687H4B···C8B2.6692
O3A···H4Ai2.0011H5A···C4A3.0347
O3A···H8Ai2.6457H5A···O2Aii2.4250
O3B···H8Biii2.5791H5A···H14B2.5494
O3B···H12Biii2.8944H5A···C7B3.0436
O3B···H4Biii2.0740H5B···O1B2.3747
N1A···O2Aii3.166 (3)H6A···O1A2.2387
N1A···N2A2.741 (2)H6B···C1Aviii3.0439
N1B···N2B2.799 (3)H6B···O1B2.5368
N2A···O3Ai2.836 (2)H7A···H14Bii2.5514
N2A···C2Bi3.432 (3)H7A···O2A2.4254
N2A···N1A2.741 (2)H7A···H13A2.5492
N2B···O3Biii2.908 (3)H7B···O2Aii2.7700
N2B···N1B2.799 (3)H7B···H9B2.5935
N2A···H8A2.6733H7B···H10B2.5404
N2B···H2Bv2.8894H7B···O2B2.4008
N2B···H8B2.7321H8A···O3Ai2.6457
C1A···O2A2.743 (3)H8A···H4A2.2132
C1B···C5Ai3.524 (4)H8A···N2A2.6733
C1B···O2B2.689 (4)H8B···N2B2.7321
C2B···C7Bv3.520 (3)H8B···O3Biii2.5791
C2B···N2Ai3.432 (3)H8B···H4B2.2287
C3A···O1Bi3.200 (3)H9B···O1Bv2.6077
C3A···O2Aii3.256 (3)H9B···H7B2.5935
C3A···C3Aii3.350 (3)H10A···H14A2.4809
C3B···C5A3.551 (3)H10B···H14B2.5273
C3B···C3Bv3.433 (3)H10B···O2Aii2.8080
C3B···O3A3.302 (3)H10B···H7B2.5404
C4A···O1Bi3.363 (3)H11A···H13A2.4647
C5A···C1Bi3.524 (4)H11A···O1Aii2.8906
C5A···C3B3.551 (3)H11B···H13B2.4899
C6A···O2Aii3.175 (3)H12B···O3Biii2.8944
C7B···C2Bv3.520 (3)H13A···O1Aix2.8645
C8B···O3Biii3.327 (3)H13A···H7A2.5492
C10B···O3Biii3.382 (4)H13A···H11A2.4647
C1A···H6Bvi3.0439H13B···H11B2.4899
C3A···H3A2.7368H14A···H10A2.4809
C3A···H2A3.0140H14B···H5A2.5494
C3B···H3B2.8474H14B···H10B2.5273
C3B···H2B3.0244H14B···H7Aii2.5514
C2A—N1A—C3A124.14 (18)H12A—C10A—H13A109.44
C2A—N1A—C6A117.28 (17)H12A—C10A—H14A109.54
C3A—N1A—C6A118.47 (16)C8A—C10A—H13A109.47
C4A—N2A—C5A123.42 (17)C8A—C10A—H14A109.46
C5A—N2A—H4A118.25C8A—C10A—H12A109.52
C4A—N2A—H4A118.32H13A—C10A—H14A109.39
O1A—C2A—N1A118.1 (3)O1B—C2B—N1B117.6 (2)
O1A—C2A—C1A122.7 (3)O1B—C2B—C1B121.3 (2)
N1A—C2A—C1A119.22 (19)N1B—C2B—C1B121.1 (3)
N1A—C3A—C4A114.57 (17)N1B—C3B—C4B117.91 (18)
O2A—C3A—N1A123.49 (19)O2B—C3B—N1B122.0 (2)
O2A—C3A—C4A121.94 (18)O2B—C3B—C4B120.1 (2)
N2A—C4A—C3A117.33 (17)N2B—C4B—C3B117.90 (19)
N2A—C4A—C7A123.57 (19)N2B—C4B—C7B122.30 (19)
C3A—C4A—C7A118.96 (19)C3B—C4B—C7B119.80 (19)
O3A—C5A—N2A123.26 (19)O3B—C5B—N2B123.4 (3)
N2A—C5A—C6A115.91 (18)N2B—C5B—C6B118.8 (3)
O3A—C5A—C6A120.83 (18)O3B—C5B—C6B117.8 (3)
N1A—C6A—C5A113.11 (17)N1B—C6B—C5B117.3 (3)
C4A—C7A—C8A128.6 (2)C4B—C7B—C8B127.71 (19)
C7A—C8A—C9A109.8 (2)C7B—C8B—C9B111.14 (19)
C7A—C8A—C10A110.1 (3)C7B—C8B—C10B110.18 (19)
C9A—C8A—C10A109.3 (2)C9B—C8B—C10B110.4 (2)
C2A—C1A—H3A109.46C2B—C1B—H1B109.41
H2A—C1A—H3A109.46C2B—C1B—H2B109.47
C2A—C1A—H2A109.50C2B—C1B—H3B109.45
C2A—C1A—H1A109.47H1B—C1B—H2B109.52
H1A—C1A—H2A109.47H1B—C1B—H3B109.49
H1A—C1A—H3A109.47H2B—C1B—H3B109.49
H5A—C6A—H6A109.45N1B—C6B—H5B107.46
N1A—C6A—H5A108.48N1B—C6B—H6B107.53
N1A—C6A—H6A108.58C5B—C6B—H5B107.48
C5A—C6A—H5A108.57C5B—C6B—H6B107.46
C5A—C6A—H6A108.60H5B—C6B—H6B109.41
C4A—C7A—H7A115.68C4B—C7B—H7B116.18
C8A—C7A—H7A115.69C8B—C7B—H7B116.11
C10A—C8A—H8A109.26C7B—C8B—H8B108.35
C7A—C8A—H8A109.19C9B—C8B—H8B108.35
C9A—C8A—H8A109.23C10B—C8B—H8B108.29
C8A—C9A—H10A109.52C8B—C9B—H9B109.50
H9A—C9A—H11A109.38C8B—C9B—H10B109.47
C8A—C9A—H9A109.48C8B—C9B—H11B109.46
H10A—C9A—H11A109.51H9B—C9B—H10B109.48
H9A—C9A—H10A109.45H9B—C9B—H11B109.43
C8A—C9A—H11A109.49H10B—C9B—H11B109.48
C2B—N1B—C3B125.08 (19)C8B—C10B—H12B109.49
C2B—N1B—C6B112.6 (2)C8B—C10B—H13B109.47
C3B—N1B—C6B122.3 (2)C8B—C10B—H14B109.47
C4B—N2B—C5B125.4 (2)H12B—C10B—H13B109.46
C5B—N2B—H4B117.31H12B—C10B—H14B109.51
C4B—N2B—H4B117.28H13B—C10B—H14B109.43
C3A—N1A—C2A—O1A172.2 (2)C4B—N2B—C5B—C6B0.5 (4)
C3A—N1A—C2A—C1A10.2 (3)C4B—N2B—C5B—O3B178.7 (3)
C6A—N1A—C2A—O1A4.0 (3)C5B—N2B—C4B—C3B2.7 (4)
C6A—N1A—C2A—C1A173.5 (2)C5B—N2B—C4B—C7B177.0 (3)
C2A—N1A—C3A—O2A19.7 (3)N1A—C3A—C4A—N2A12.1 (3)
C2A—N1A—C3A—C4A160.2 (2)O2A—C3A—C4A—C7A8.1 (3)
C6A—N1A—C3A—O2A156.5 (2)N1A—C3A—C4A—C7A171.97 (19)
C6A—N1A—C3A—C4A23.6 (3)O2A—C3A—C4A—N2A167.8 (2)
C2A—N1A—C6A—C5A137.8 (2)C3A—C4A—C7A—C8A178.0 (2)
C3A—N1A—C6A—C5A45.7 (2)N2A—C4A—C7A—C8A2.4 (4)
C5A—N2A—C4A—C3A27.2 (3)N2A—C5A—C6A—N1A30.9 (3)
C5A—N2A—C4A—C7A157.1 (2)O3A—C5A—C6A—N1A149.42 (19)
C4A—N2A—C5A—O3A175.3 (2)C4A—C7A—C8A—C9A110.8 (3)
C4A—N2A—C5A—C6A4.4 (3)C4A—C7A—C8A—C10A128.8 (3)
C6B—N1B—C2B—O1B1.2 (3)O2B—C3B—C4B—N2B180.0 (2)
C6B—N1B—C2B—C1B179.0 (2)O2B—C3B—C4B—C7B0.3 (3)
C3B—N1B—C2B—O1B179.8 (2)N1B—C3B—C4B—C7B179.7 (2)
C2B—N1B—C3B—O2B3.7 (3)N1B—C3B—C4B—N2B0.0 (3)
C2B—N1B—C3B—C4B176.26 (19)C3B—C4B—C7B—C8B179.1 (2)
C2B—N1B—C6B—C5B174.0 (2)N2B—C4B—C7B—C8B1.2 (4)
C3B—N1B—C2B—C1B0.0 (3)O3B—C5B—C6B—N1B176.6 (3)
C3B—N1B—C6B—C5B6.9 (4)N2B—C5B—C6B—N1B4.2 (4)
C6B—N1B—C3B—O2B175.2 (2)C4B—C7B—C8B—C9B154.1 (2)
C6B—N1B—C3B—C4B4.8 (3)C4B—C7B—C8B—C10B83.1 (3)
Symmetry codes: (i) x, y+2, z+2; (ii) x1, y+2, z+2; (iii) x, y+1, z+1; (iv) x, y, z1; (v) x, y+1, z+2; (vi) x1, y+1, z; (vii) x, y+2, z+3; (viii) x+1, y1, z; (ix) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H4A···O3Ai0.852.002.836 (2)167
N2B—H4B···O3Biii0.852.072.908 (3)167
C6A—H5A···O2Aii0.952.423.175 (3)136
C6A—H6A···O1A0.952.242.659 (3)106
C7A—H7A···O2A0.952.432.790 (3)103
C7B—H7B···O2B0.952.402.764 (3)102
C8B—H8B···O3Biii0.952.583.327 (3)136
Symmetry codes: (i) x, y+2, z+2; (ii) x1, y+2, z+2; (iii) x, y+1, z+1.
 

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