The title compound, C10H10N2O4, crystallizes with two independent molecules (A and B) in the asymmetric unit. The five-membered ring of the oxazole moiety adopts a half-chair conformation in molecule A and an envelope conformation in molecule B. The oxazine ring adopts a sofa conformation in both molecules.
Supporting information
CCDC reference: 206793
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.076
- wR factor = 0.095
- Data-to-parameter ratio = 10.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.
7-nitro-1,2,3a,4-tetrahydrobenzo[
b][1,3] oxazolo [3,2-
d] oxazine.
top
Crystal data top
C10H10N2O4 | F(000) = 928 |
Mr = 222.20 | Dx = 1.518 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 12.164 (2) Å | θ = 25.8–29.5° |
b = 22.079 (4) Å | µ = 1.02 mm−1 |
c = 7.373 (2) Å | T = 298 K |
β = 100.86 (2)° | Block, yellow |
V = 1944.6 (6) Å3 | 0.45 × 0.30 × 0.20 mm |
Z = 8 | |
Data collection top
Rigaku AFC-7S diffractometer | 3111 reflections with I > 0.5σ(I) |
Radiation source: X-ray tube | Rint = 0.082 |
Graphite monochromator | θmax = 70.0°, θmin = 3.7° |
ω–2θ scans | h = −14→14 |
Absorption correction: ψ scans (North et al., 1968) | k = 0→26 |
Tmin = 0.586, Tmax = 0.816 | l = −8→3 |
4615 measured reflections | 3 standard reflections every 150 reflections |
3769 independent reflections | intensity decay: ca 1.0% |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.88 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00016|Fo|2] |
3111 reflections | (Δ/σ)max = 0.002 |
289 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
0 constraints | |
Special details top
Experimental. The scan width was (0.94 + 0.14tanθ)° with an ω scan speed of 16° per minute
(up to 5 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. Structure was solved using direct methods (Altomare, A., et al. 1993).
All calculations were performed using the TEXSAN software (Molecular
Structure Corporation, USA. 1995). |
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6548 (2) | 0.21548 (10) | 0.9011 (5) | 0.0968 (12) | |
O2A | 0.4842 (3) | 0.24644 (10) | 0.8424 (6) | 0.1052 (12) | |
O3A | 0.25269 (15) | 0.06662 (7) | 0.6542 (3) | 0.0609 (6) | |
O4A | 0.2666 (2) | −0.09694 (8) | 0.6910 (3) | 0.0682 (7) | |
N1A | 0.5547 (2) | 0.20619 (11) | 0.8519 (4) | 0.0667 (9) | |
N2A | 0.4022 (2) | −0.02843 (9) | 0.6698 (3) | 0.0553 (7) | |
C1A | 0.4420 (2) | 0.02731 (10) | 0.7234 (3) | 0.0464 (8) | |
C2A | 0.5564 (2) | 0.03956 (12) | 0.7866 (4) | 0.0530 (8) | |
C3A | 0.5936 (2) | 0.09786 (13) | 0.8288 (4) | 0.0558 (9) | |
C4A | 0.5167 (2) | 0.14498 (11) | 0.8070 (4) | 0.0509 (8) | |
C5A | 0.4023 (2) | 0.13494 (11) | 0.7490 (4) | 0.0493 (8) | |
C6A | 0.3663 (2) | 0.07653 (10) | 0.7105 (3) | 0.0469 (7) | |
C7A | 0.2191 (2) | 0.00777 (12) | 0.7019 (5) | 0.0637 (9) | |
C8A | 0.2832 (3) | −0.03962 (11) | 0.6198 (4) | 0.0570 (8) | |
C9A | 0.3635 (3) | −0.13108 (13) | 0.6696 (4) | 0.0691 (10) | |
C10A | 0.4607 (3) | −0.08576 (11) | 0.7097 (4) | 0.0588 (9) | |
O1B | −0.01649 (19) | 0.07853 (8) | 0.6470 (3) | 0.0685 (8) | |
O2B | −0.15667 (17) | 0.11282 (8) | 0.7561 (3) | 0.0639 (7) | |
O3B | 0.21392 (14) | 0.25794 (7) | 0.5836 (3) | 0.0484 (6) | |
O4B | 0.22258 (19) | 0.42080 (8) | 0.6650 (3) | 0.0682 (7) | |
N1B | −0.07256 (17) | 0.12092 (8) | 0.6888 (3) | 0.0468 (6) | |
N2B | 0.07491 (18) | 0.35619 (8) | 0.6048 (3) | 0.0502 (7) | |
C1B | 0.03669 (19) | 0.29907 (9) | 0.6315 (3) | 0.0408 (7) | |
C2B | −0.0706 (2) | 0.28824 (10) | 0.6671 (3) | 0.0446 (7) | |
C3B | −0.10744 (19) | 0.22985 (10) | 0.6859 (3) | 0.0445 (7) | |
C4B | −0.03709 (19) | 0.18198 (9) | 0.6640 (3) | 0.0402 (6) | |
C5B | 0.06969 (18) | 0.19106 (9) | 0.6252 (3) | 0.0392 (6) | |
C6B | 0.10731 (18) | 0.24923 (9) | 0.6140 (3) | 0.0380 (6) | |
C7B | 0.2623 (2) | 0.31405 (10) | 0.6566 (4) | 0.0546 (8) | |
C8B | 0.1887 (2) | 0.36560 (11) | 0.5767 (4) | 0.0532 (8) | |
C9B | 0.1236 (3) | 0.45497 (12) | 0.6574 (6) | 0.0791 (13) | |
C10B | 0.0321 (3) | 0.41140 (10) | 0.6750 (4) | 0.0553 (8) | |
H1A | 0.60882 | 0.00719 | 0.80103 | 0.0652* | |
H2A | 0.67083 | 0.10574 | 0.87212 | 0.0682* | |
H3A | 0.35059 | 0.16763 | 0.73687 | 0.0596* | |
H4A | 0.23381 | 0.00365 | 0.83246 | 0.0772* | |
H5A | 0.14136 | 0.00261 | 0.65602 | 0.0772* | |
H6A | 0.26082 | −0.03970 | 0.48911 | 0.0697* | |
H7A | 0.37544 | −0.16377 | 0.75488 | 0.0842* | |
H8A | 0.35570 | −0.14639 | 0.54742 | 0.0842* | |
H9A | 0.51302 | −0.09216 | 0.63070 | 0.0712* | |
H10A | 0.49827 | −0.08796 | 0.83478 | 0.0712* | |
H1B | −0.11847 | 0.32141 | 0.67917 | 0.0539* | |
H2B | −0.17969 | 0.22256 | 0.71255 | 0.0547* | |
H3B | 0.11543 | 0.15757 | 0.60722 | 0.0479* | |
H4B | 0.26858 | 0.31410 | 0.78707 | 0.0677* | |
H5B | 0.33452 | 0.31862 | 0.62682 | 0.0677* | |
H6B | 0.18925 | 0.36890 | 0.44830 | 0.0649* | |
H7B | 0.13291 | 0.48350 | 0.75557 | 0.0963* | |
H8B | 0.10601 | 0.47585 | 0.54266 | 0.0963* | |
H9B | −0.03724 | 0.42332 | 0.60133 | 0.0681* | |
H10B | 0.02342 | 0.40716 | 0.79980 | 0.0681* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0486 (13) | 0.0684 (14) | 0.168 (3) | −0.0149 (16) | 0.0067 (14) | 0.0116 (11) |
O2A | 0.0650 (16) | 0.0487 (11) | 0.193 (3) | −0.0008 (15) | 0.0016 (18) | −0.0112 (11) |
O3A | 0.0409 (10) | 0.0413 (9) | 0.0969 (14) | 0.0055 (9) | 0.0037 (9) | −0.0049 (7) |
O4A | 0.0753 (14) | 0.0413 (9) | 0.0921 (15) | 0.0037 (9) | 0.0266 (11) | 0.0025 (9) |
N1A | 0.0536 (14) | 0.0522 (12) | 0.0940 (19) | −0.0078 (12) | 0.0132 (12) | 0.0094 (10) |
N2A | 0.0543 (13) | 0.0441 (11) | 0.0679 (14) | 0.0113 (9) | 0.0127 (10) | −0.0042 (9) |
C1A | 0.0497 (14) | 0.0438 (12) | 0.0485 (13) | 0.0119 (9) | 0.0162 (10) | 0.0052 (10) |
C2A | 0.0459 (14) | 0.0536 (13) | 0.0632 (15) | 0.0124 (11) | 0.0194 (11) | 0.0083 (11) |
C3A | 0.0378 (12) | 0.0646 (16) | 0.0668 (16) | 0.0032 (12) | 0.0141 (11) | 0.0092 (11) |
C4A | 0.0451 (13) | 0.0474 (13) | 0.0624 (15) | −0.0012 (11) | 0.0158 (11) | 0.0085 (10) |
C5A | 0.0433 (13) | 0.0431 (11) | 0.0627 (15) | 0.0052 (10) | 0.0131 (10) | 0.0041 (10) |
C6A | 0.0399 (12) | 0.0437 (12) | 0.0578 (14) | 0.0053 (10) | 0.0112 (10) | 0.0001 (9) |
C7A | 0.0466 (14) | 0.0471 (13) | 0.098 (2) | 0.0004 (14) | 0.0155 (14) | −0.0092 (11) |
C8A | 0.0568 (15) | 0.0419 (12) | 0.0715 (16) | 0.0059 (11) | 0.0102 (12) | −0.0012 (11) |
C9A | 0.090 (2) | 0.0450 (14) | 0.0740 (18) | 0.0198 (13) | 0.0201 (16) | 0.0027 (14) |
C10A | 0.0699 (18) | 0.0457 (13) | 0.0638 (16) | 0.0211 (11) | 0.0203 (13) | 0.0045 (12) |
O1B | 0.0639 (12) | 0.0346 (9) | 0.1135 (17) | 0.0004 (9) | 0.0334 (11) | −0.0001 (8) |
O2B | 0.0556 (11) | 0.0551 (10) | 0.0876 (14) | −0.0147 (9) | 0.0302 (10) | 0.0016 (9) |
O3B | 0.0364 (9) | 0.0373 (8) | 0.0741 (12) | −0.0017 (7) | 0.0171 (8) | −0.0041 (6) |
O4B | 0.0639 (13) | 0.0380 (9) | 0.1007 (16) | −0.0103 (9) | 0.0101 (11) | −0.0105 (8) |
N1B | 0.0415 (10) | 0.0385 (10) | 0.0598 (12) | −0.0062 (8) | 0.0081 (9) | 0.0011 (8) |
N2B | 0.0502 (12) | 0.0317 (9) | 0.0712 (14) | 0.0012 (8) | 0.0177 (9) | −0.0018 (8) |
C1B | 0.0426 (12) | 0.0329 (10) | 0.0470 (12) | 0.0044 (8) | 0.0090 (9) | 0.0002 (9) |
C2B | 0.0412 (12) | 0.0380 (11) | 0.0563 (14) | 0.0086 (9) | 0.0135 (9) | 0.0007 (9) |
C3B | 0.0356 (11) | 0.0455 (11) | 0.0528 (13) | 0.0005 (10) | 0.0094 (9) | 0.0023 (9) |
C4B | 0.0392 (11) | 0.0342 (10) | 0.0473 (12) | −0.0026 (8) | 0.0083 (9) | 0.0020 (8) |
C5B | 0.0361 (11) | 0.0329 (10) | 0.0483 (12) | 0.0031 (8) | 0.0068 (9) | −0.0007 (8) |
C6B | 0.0326 (11) | 0.0357 (10) | 0.0466 (11) | −0.0001 (8) | 0.0094 (8) | −0.0019 (8) |
C7B | 0.0438 (13) | 0.0421 (12) | 0.0774 (18) | −0.0088 (12) | 0.0102 (11) | 0.0004 (10) |
C8B | 0.0567 (15) | 0.0386 (12) | 0.0654 (15) | −0.0089 (11) | 0.0142 (12) | −0.0049 (10) |
C9B | 0.084 (2) | 0.0389 (13) | 0.118 (3) | −0.0013 (15) | 0.028 (2) | −0.0107 (14) |
C10B | 0.0700 (17) | 0.0317 (10) | 0.0665 (16) | 0.0059 (10) | 0.0186 (13) | −0.0022 (10) |
Geometric parameters (Å, º) top
O1A—N1A | 1.221 (4) | C2A—H1A | 0.9503 |
O2A—N1A | 1.228 (4) | C3A—H2A | 0.9496 |
O3A—C6A | 1.383 (3) | C5A—H3A | 0.9505 |
O3A—C7A | 1.426 (3) | C7A—H5A | 0.9493 |
O4A—C8A | 1.399 (3) | C7A—H4A | 0.9498 |
O4A—C9A | 1.433 (4) | C8A—H6A | 0.9507 |
O1B—N1B | 1.231 (3) | C9A—H7A | 0.9503 |
O2B—N1B | 1.231 (3) | C9A—H8A | 0.9500 |
O3B—C6B | 1.371 (3) | C10A—H9A | 0.9507 |
O3B—C7B | 1.432 (3) | C10A—H10A | 0.9502 |
O4B—C8B | 1.406 (3) | C1B—C2B | 1.399 (3) |
O4B—C9B | 1.413 (4) | C1B—C6B | 1.417 (3) |
N1A—C4A | 1.446 (4) | C2B—C3B | 1.380 (3) |
N2A—C8A | 1.446 (4) | C3B—C4B | 1.388 (3) |
N2A—C1A | 1.354 (3) | C4B—C5B | 1.396 (3) |
N2A—C10A | 1.455 (3) | C5B—C6B | 1.371 (3) |
N1B—C4B | 1.438 (3) | C7B—C8B | 1.498 (4) |
N2B—C1B | 1.371 (3) | C9B—C10B | 1.495 (5) |
N2B—C8B | 1.453 (3) | C2B—H1B | 0.9502 |
N2B—C10B | 1.458 (3) | C3B—H2B | 0.9497 |
C1A—C2A | 1.408 (4) | C5B—H3B | 0.9496 |
C1A—C6A | 1.416 (3) | C7B—H4B | 0.9505 |
C2A—C3A | 1.380 (4) | C7B—H5B | 0.9501 |
C3A—C4A | 1.388 (4) | C8B—H6B | 0.9508 |
C4A—C5A | 1.394 (4) | C9B—H7B | 0.9501 |
C5A—C6A | 1.374 (3) | C9B—H8B | 0.9517 |
C7A—C8A | 1.499 (4) | C10B—H9B | 0.9503 |
C9A—C10A | 1.535 (5) | C10B—H10B | 0.9504 |
| | | |
O1B···C7A | 3.222 (4) | C1B···H4B | 2.8571 |
O2A···C7B | 3.162 (4) | C2A···H10A | 2.9407 |
O2A···C9Ai | 3.289 (4) | C2B···H10B | 2.9559 |
O2B···C3Aii | 3.200 (3) | C2B···H9B | 3.0609 |
O2B···C8Aiii | 3.325 (4) | C3A···H10Aiv | 2.9143 |
O3A···N2A | 2.765 (3) | C4A···H10Aiv | 2.9623 |
O3B···N2B | 2.773 (3) | C5B···H6Bviii | 2.8701 |
O1A···H7Aiv | 2.8677 | C9B···H4Avii | 3.0954 |
O1A···H7Ai | 2.8994 | C10A···H1A | 2.7302 |
O1A···H2Bv | 2.6579 | C10B···H1B | 2.7063 |
O1A···H2A | 2.4434 | H1A···H10A | 2.5317 |
O1B···H3B | 2.4256 | H1A···C10A | 2.7302 |
O1B···H7Bvi | 2.7031 | H1A···O4Bix | 2.7773 |
O1B···H10Bvii | 2.7123 | H1B···C10B | 2.7063 |
O1B···H5A | 2.5402 | H1B···O4Ax | 2.8395 |
O2A···H5B | 2.7001 | H1B···H9B | 2.5656 |
O2A···H7Ai | 2.7966 | H2A···O2Bv | 2.4156 |
O2A···H3A | 2.4079 | H2A···O1A | 2.4434 |
O2B···H2Aii | 2.4156 | H2B···O1Aii | 2.6579 |
O2B···H7Bvi | 2.8728 | H2B···O2B | 2.4532 |
O2B···H9Bviii | 2.7987 | H3A···O2A | 2.4079 |
O2B···H2B | 2.4532 | H3A···O3B | 2.7035 |
O2B···H6Aiii | 2.5724 | H3B···O1B | 2.4256 |
O3A···H6Bviii | 2.8204 | H3B···H6Bviii | 2.5732 |
O3A···H3B | 2.5927 | H3B···O3A | 2.5927 |
O3B···H4Bvii | 2.8809 | H4A···C9Bviii | 3.0954 |
O3B···H3A | 2.7035 | H4A···H8Bviii | 2.4354 |
O4A···H1Bvi | 2.8395 | H4A···C1A | 2.8460 |
O4B···H1Ai | 2.7773 | H4B···C1B | 2.8571 |
N1B···N2Bviii | 3.288 (3) | H4B···O3Bviii | 2.8809 |
N2A···O3A | 2.765 (3) | H5A···O1B | 2.5402 |
N2B···O3B | 2.773 (3) | H5B···O2A | 2.7001 |
N2B···N1Bvii | 3.288 (3) | H6A···H7Bvii | 2.4323 |
N2B···C4Bvii | 3.385 (3) | H6A···O2Biii | 2.5724 |
C1B···C5Bviii | 3.593 (3) | H6B···O3Avii | 2.8204 |
C1B···C3Bvii | 3.479 (3) | H6B···C5Bvii | 2.8701 |
C1B···C4Bvii | 3.420 (3) | H6B···H3Bvii | 2.5732 |
C2B···C5Bviii | 3.515 (3) | H7A···O2Aix | 2.7966 |
C2B···C3Bvii | 3.514 (3) | H7A···O1Aiv | 2.8677 |
C3A···C10Aiv | 3.596 (4) | H7A···O1Aix | 2.8994 |
C3A···O2Bv | 3.200 (3) | H7B···H6Aviii | 2.4323 |
C3B···C1Bviii | 3.479 (3) | H7B···O1Bx | 2.7031 |
C3B···C2Bviii | 3.514 (3) | H7B···O2Bx | 2.8728 |
C4B···C1Bviii | 3.420 (3) | H8B···H9Bxi | 2.5394 |
C4B···N2Bviii | 3.385 (3) | H8B···H4Avii | 2.4354 |
C5B···C2Bvii | 3.515 (3) | H9B···H8Bxi | 2.5394 |
C5B···C8Bviii | 3.595 (4) | H9B···O2Bvii | 2.7987 |
C5B···C1Bvii | 3.593 (3) | H9B···H1B | 2.5656 |
C7A···O1B | 3.222 (4) | H9B···C2B | 3.0609 |
C7B···O2A | 3.162 (4) | H10A···C2A | 2.9407 |
C8A···O2Biii | 3.325 (4) | H10A···H1A | 2.5317 |
C8B···C5Bvii | 3.595 (4) | H10A···C3Aiv | 2.9143 |
C9A···O2Aix | 3.289 (4) | H10A···C4Aiv | 2.9623 |
C10A···C3Aiv | 3.596 (4) | H10B···C2B | 2.9559 |
C1A···H4A | 2.8460 | H10B···O1Bviii | 2.7123 |
| | | |
C6A—O3A—C7A | 112.74 (19) | C10A—C9A—H8A | 110.51 |
C8A—O4A—C9A | 104.8 (2) | H7A—C9A—H8A | 109.43 |
C6B—O3B—C7B | 113.23 (18) | C10A—C9A—H7A | 110.59 |
C8B—O4B—C9B | 105.7 (2) | N2A—C10A—H9A | 111.33 |
O1A—N1A—C4A | 118.9 (2) | N2A—C10A—H10A | 111.61 |
O1A—N1A—O2A | 122.8 (3) | C9A—C10A—H10A | 111.46 |
O2A—N1A—C4A | 118.3 (3) | H9A—C10A—H10A | 109.39 |
C8A—N2A—C10A | 109.3 (2) | C9A—C10A—H9A | 111.43 |
C1A—N2A—C10A | 126.7 (2) | N2B—C1B—C2B | 122.5 (2) |
C1A—N2A—C8A | 121.0 (2) | N2B—C1B—C6B | 118.3 (2) |
O2B—N1B—C4B | 118.65 (19) | C2B—C1B—C6B | 119.16 (19) |
O1B—N1B—O2B | 122.1 (2) | C1B—C2B—C3B | 120.7 (2) |
O1B—N1B—C4B | 119.2 (2) | C2B—C3B—C4B | 118.7 (2) |
C1B—N2B—C10B | 124.4 (2) | N1B—C4B—C3B | 119.5 (2) |
C8B—N2B—C10B | 110.2 (2) | N1B—C4B—C5B | 118.28 (19) |
C1B—N2B—C8B | 120.67 (19) | C3B—C4B—C5B | 122.15 (19) |
N2A—C1A—C2A | 123.2 (2) | C4B—C5B—C6B | 118.74 (19) |
N2A—C1A—C6A | 119.1 (2) | O3B—C6B—C1B | 120.96 (18) |
C2A—C1A—C6A | 117.7 (2) | O3B—C6B—C5B | 118.56 (19) |
C1A—C2A—C3A | 121.0 (2) | C1B—C6B—C5B | 120.5 (2) |
C2A—C3A—C4A | 119.2 (2) | O3B—C7B—C8B | 109.7 (2) |
N1A—C4A—C5A | 118.4 (2) | O4B—C8B—N2B | 105.2 (2) |
C3A—C4A—C5A | 121.9 (2) | O4B—C8B—C7B | 112.0 (2) |
N1A—C4A—C3A | 119.6 (2) | N2B—C8B—C7B | 110.5 (2) |
C4A—C5A—C6A | 118.2 (2) | O4B—C9B—C10B | 107.2 (2) |
O3A—C6A—C1A | 119.9 (2) | N2B—C10B—C9B | 100.7 (3) |
O3A—C6A—C5A | 118.2 (2) | C1B—C2B—H1B | 119.70 |
C1A—C6A—C5A | 121.9 (2) | C3B—C2B—H1B | 119.62 |
O3A—C7A—C8A | 110.0 (2) | C2B—C3B—H2B | 120.64 |
O4A—C8A—N2A | 105.5 (2) | C4B—C3B—H2B | 120.64 |
O4A—C8A—C7A | 110.9 (3) | C4B—C5B—H3B | 120.60 |
N2A—C8A—C7A | 110.5 (2) | C6B—C5B—H3B | 120.67 |
O4A—C9A—C10A | 104.8 (2) | O3B—C7B—H4B | 109.29 |
N2A—C10A—C9A | 101.5 (3) | O3B—C7B—H5B | 109.71 |
C3A—C2A—H1A | 119.44 | C8B—C7B—H4B | 108.97 |
C1A—C2A—H1A | 119.54 | C8B—C7B—H5B | 109.78 |
C4A—C3A—H2A | 120.27 | H4B—C7B—H5B | 109.40 |
C2A—C3A—H2A | 120.54 | O4B—C8B—H6B | 109.76 |
C4A—C5A—H3A | 120.84 | N2B—C8B—H6B | 109.79 |
C6A—C5A—H3A | 120.91 | C7B—C8B—H6B | 109.51 |
O3A—C7A—H5A | 109.51 | O4B—C9B—H7B | 110.21 |
C8A—C7A—H4A | 109.23 | O4B—C9B—H8B | 109.94 |
O3A—C7A—H4A | 109.22 | C10B—C9B—H7B | 110.14 |
C8A—C7A—H5A | 109.35 | C10B—C9B—H8B | 110.02 |
H4A—C7A—H5A | 109.54 | H7B—C9B—H8B | 109.31 |
O4A—C8A—H6A | 110.16 | N2B—C10B—H9B | 111.50 |
N2A—C8A—H6A | 109.91 | N2B—C10B—H10B | 111.93 |
C7A—C8A—H6A | 109.83 | C9B—C10B—H9B | 111.55 |
O4A—C9A—H7A | 110.68 | C9B—C10B—H10B | 111.57 |
O4A—C9A—H8A | 110.75 | H9B—C10B—H10B | 109.40 |
| | | |
C7A—O3A—C6A—C1A | 29.5 (3) | C8B—N2B—C10B—C9B | 8.1 (3) |
C7A—O3A—C6A—C5A | −151.8 (2) | C8B—N2B—C1B—C2B | 177.1 (2) |
C6A—O3A—C7A—C8A | −57.4 (3) | C8B—N2B—C1B—C6B | −5.7 (3) |
C9A—O4A—C8A—N2A | −35.9 (3) | C1B—N2B—C10B—C9B | 163.5 (3) |
C9A—O4A—C8A—C7A | −155.5 (3) | N2A—C1A—C2A—C3A | 175.9 (3) |
C8A—O4A—C9A—C10A | 37.4 (3) | C6A—C1A—C2A—C3A | −2.0 (4) |
C7B—O3B—C6B—C1B | 28.0 (3) | C2A—C1A—C6A—C5A | 3.2 (3) |
C6B—O3B—C7B—C8B | −56.7 (3) | C2A—C1A—C6A—O3A | −178.2 (2) |
C7B—O3B—C6B—C5B | −152.7 (2) | N2A—C1A—C6A—O3A | 3.8 (3) |
C9B—O4B—C8B—N2B | −28.5 (3) | N2A—C1A—C6A—C5A | −174.9 (2) |
C8B—O4B—C9B—C10B | 34.7 (3) | C1A—C2A—C3A—C4A | −0.5 (4) |
C9B—O4B—C8B—C7B | −148.5 (3) | C2A—C3A—C4A—C5A | 2.0 (4) |
O1A—N1A—C4A—C5A | −179.3 (3) | C2A—C3A—C4A—N1A | 179.6 (3) |
O1A—N1A—C4A—C3A | 3.0 (4) | C3A—C4A—C5A—C6A | −0.9 (4) |
O2A—N1A—C4A—C5A | 2.2 (5) | N1A—C4A—C5A—C6A | −178.5 (3) |
O2A—N1A—C4A—C3A | −175.5 (3) | C4A—C5A—C6A—C1A | −1.7 (4) |
C8A—N2A—C10A—C9A | 2.3 (3) | C4A—C5A—C6A—O3A | 179.6 (2) |
C10A—N2A—C8A—C7A | 140.5 (2) | O3A—C7A—C8A—N2A | 52.9 (3) |
C8A—N2A—C1A—C2A | 175.1 (2) | O3A—C7A—C8A—O4A | 169.5 (2) |
C10A—N2A—C1A—C2A | 16.7 (4) | O4A—C9A—C10A—N2A | −23.7 (3) |
C10A—N2A—C1A—C6A | −165.4 (2) | N2B—C1B—C2B—C3B | 177.4 (2) |
C8A—N2A—C1A—C6A | −7.0 (3) | C2B—C1B—C6B—O3B | −178.4 (2) |
C10A—N2A—C8A—O4A | 20.5 (3) | C2B—C1B—C6B—C5B | 2.3 (3) |
C1A—N2A—C8A—O4A | −141.2 (2) | N2B—C1B—C6B—O3B | 4.4 (3) |
C1A—N2A—C10A—C9A | 162.7 (2) | N2B—C1B—C6B—C5B | −174.9 (2) |
C1A—N2A—C8A—C7A | −21.3 (3) | C6B—C1B—C2B—C3B | 0.3 (3) |
O2B—N1B—C4B—C5B | 166.7 (2) | C1B—C2B—C3B—C4B | −1.7 (3) |
O2B—N1B—C4B—C3B | −10.9 (3) | C2B—C3B—C4B—N1B | 178.0 (2) |
O1B—N1B—C4B—C5B | −11.4 (3) | C2B—C3B—C4B—C5B | 0.5 (3) |
O1B—N1B—C4B—C3B | 171.0 (2) | C3B—C4B—C5B—C6B | 2.0 (3) |
C1B—N2B—C8B—O4B | −144.4 (2) | N1B—C4B—C5B—C6B | −175.5 (2) |
C10B—N2B—C1B—C2B | 24.1 (4) | C4B—C5B—C6B—C1B | −3.4 (3) |
C10B—N2B—C1B—C6B | −158.7 (2) | C4B—C5B—C6B—O3B | 177.3 (2) |
C10B—N2B—C8B—C7B | 133.2 (2) | O3B—C7B—C8B—N2B | 53.6 (3) |
C1B—N2B—C8B—C7B | −23.3 (3) | O3B—C7B—C8B—O4B | 170.6 (2) |
C10B—N2B—C8B—O4B | 12.1 (3) | O4B—C9B—C10B—N2B | −25.7 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+2; (v) x+1, y, z; (vi) −x, y−1/2, −z+3/2; (vii) x, −y+1/2, z−1/2; (viii) x, −y+1/2, z+1/2; (ix) −x+1, y−1/2, −z+3/2; (x) −x, y+1/2, −z+3/2; (xi) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H2A···O2Bv | 0.95 | 2.42 | 3.200 (3) | 140 |
C5B—H3B···O3A | 0.95 | 2.59 | 3.517 (3) | 165 |
C7A—H5A···O1B | 0.95 | 2.54 | 3.222 (4) | 129 |
C8A—H6A···O2Biii | 0.95 | 2.57 | 3.325 (4) | 136 |
Symmetry codes: (iii) −x, −y, −z+1; (v) x+1, y, z. |