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
CCDC reference: 227018
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-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 reflections | Δρmax = 0.26 e Å−3 |
272 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···C3Ai | 3.200 (3) | C4A···H5A | 3.0347 |
O1B···C4Ai | 3.363 (3) | C4B···H2Bv | 2.9209 |
O2A···N1Aii | 3.166 (3) | C5A···H4Ai | 2.8822 |
O2A···C1A | 2.743 (3) | C5B···H4Biii | 3.0326 |
O2A···C3Aii | 3.256 (3) | C7B···H5A | 3.0436 |
O2A···C6Aii | 3.175 (3) | C8A···H4A | 2.8118 |
O2B···C1B | 2.689 (4) | C8B···H4B | 2.6692 |
O3A···C3B | 3.302 (3) | C10A···H1Bvii | 3.0796 |
O3A···N2Ai | 2.836 (2) | H1B···C10Avii | 3.0796 |
O3B···C8Biii | 3.327 (3) | H2A···C3A | 3.0140 |
O3B···N2Biii | 2.908 (3) | H2A···O2A | 2.5283 |
O3B···C10Biii | 3.382 (4) | H2A···O2Bii | 2.7932 |
O1A···H11Aii | 2.8906 | H2B···N2Bv | 2.8894 |
O1A···H6A | 2.2387 | H2B···C3B | 3.0244 |
O1A···H13Aiv | 2.8645 | H2B···C4Bv | 2.9209 |
O1B···H6B | 2.5368 | H2B···O2B | 2.5532 |
O1B···H9Bv | 2.6077 | H3A···O2A | 2.4980 |
O1B···H5B | 2.3747 | H3A···C3A | 2.7368 |
O2A···H7Bii | 2.7700 | H3B···O2B | 2.3687 |
O2A···H2A | 2.5283 | H3B···C3B | 2.8474 |
O2A···H5Aii | 2.4250 | H4A···C5Ai | 2.8822 |
O2A···H3A | 2.4980 | H4A···O3Ai | 2.0011 |
O2A···H7A | 2.4254 | H4A···H8A | 2.2132 |
O2A···H10Bii | 2.8080 | H4A···C8A | 2.8118 |
O2B···H2B | 2.5532 | H4B···C5Biii | 3.0326 |
O2B···H7B | 2.4008 | H4B···O3Biii | 2.0740 |
O2B···H2Aii | 2.7932 | H4B···H8B | 2.2287 |
O2B···H3B | 2.3687 | H4B···C8B | 2.6692 |
O3A···H4Ai | 2.0011 | H5A···C4A | 3.0347 |
O3A···H8Ai | 2.6457 | H5A···O2Aii | 2.4250 |
O3B···H8Biii | 2.5791 | H5A···H14B | 2.5494 |
O3B···H12Biii | 2.8944 | H5A···C7B | 3.0436 |
O3B···H4Biii | 2.0740 | H5B···O1B | 2.3747 |
N1A···O2Aii | 3.166 (3) | H6A···O1A | 2.2387 |
N1A···N2A | 2.741 (2) | H6B···C1Aviii | 3.0439 |
N1B···N2B | 2.799 (3) | H6B···O1B | 2.5368 |
N2A···O3Ai | 2.836 (2) | H7A···H14Bii | 2.5514 |
N2A···C2Bi | 3.432 (3) | H7A···O2A | 2.4254 |
N2A···N1A | 2.741 (2) | H7A···H13A | 2.5492 |
N2B···O3Biii | 2.908 (3) | H7B···O2Aii | 2.7700 |
N2B···N1B | 2.799 (3) | H7B···H9B | 2.5935 |
N2A···H8A | 2.6733 | H7B···H10B | 2.5404 |
N2B···H2Bv | 2.8894 | H7B···O2B | 2.4008 |
N2B···H8B | 2.7321 | H8A···O3Ai | 2.6457 |
C1A···O2A | 2.743 (3) | H8A···H4A | 2.2132 |
C1B···C5Ai | 3.524 (4) | H8A···N2A | 2.6733 |
C1B···O2B | 2.689 (4) | H8B···N2B | 2.7321 |
C2B···C7Bv | 3.520 (3) | H8B···O3Biii | 2.5791 |
C2B···N2Ai | 3.432 (3) | H8B···H4B | 2.2287 |
C3A···O1Bi | 3.200 (3) | H9B···O1Bv | 2.6077 |
C3A···O2Aii | 3.256 (3) | H9B···H7B | 2.5935 |
C3A···C3Aii | 3.350 (3) | H10A···H14A | 2.4809 |
C3B···C5A | 3.551 (3) | H10B···H14B | 2.5273 |
C3B···C3Bv | 3.433 (3) | H10B···O2Aii | 2.8080 |
C3B···O3A | 3.302 (3) | H10B···H7B | 2.5404 |
C4A···O1Bi | 3.363 (3) | H11A···H13A | 2.4647 |
C5A···C1Bi | 3.524 (4) | H11A···O1Aii | 2.8906 |
C5A···C3B | 3.551 (3) | H11B···H13B | 2.4899 |
C6A···O2Aii | 3.175 (3) | H12B···O3Biii | 2.8944 |
C7B···C2Bv | 3.520 (3) | H13A···O1Aix | 2.8645 |
C8B···O3Biii | 3.327 (3) | H13A···H7A | 2.5492 |
C10B···O3Biii | 3.382 (4) | H13A···H11A | 2.4647 |
C1A···H6Bvi | 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···H7Aii | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H4A···O3Ai | 0.85 | 2.00 | 2.836 (2) | 167 |
N2B—H4B···O3Biii | 0.85 | 2.07 | 2.908 (3) | 167 |
C6A—H5A···O2Aii | 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···O3Biii | 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. |