In the title enaminone, C
13H
19N
1O
4, the Meldrum's acid group has a distorted boat conformation. The two independent molecules of the asymmetric unit are dimerized about a pseudo inversion center through two intermolecular N—H
O hydrogen bonds, with N
O distances of 3.049 (4) and 3.093 (4) Å. The dimers are stacked along the [010] direction.
Supporting information
CCDC reference: 618975
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.006 Å
- R factor = 0.057
- wR factor = 0.204
- Data-to-parameter ratio = 7.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.70
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 67.95
From the CIF: _reflns_number_total 2558
Count of symmetry unique reflns 2560
Completeness (_total/calc) 99.92%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).
5-[(Cyclohexylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
top
Crystal data top
C13H19NO4 | Dx = 1.258 Mg m−3 |
Mr = 253.29 | Melting point = 421–422 K |
Orthorhombic, Pca21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
a = 20.905 (2) Å | θ = 17.8–31.8° |
b = 10.222 (1) Å | µ = 0.77 mm−1 |
c = 12.516 (6) Å | T = 297 K |
V = 2674.6 (13) Å3 | Prism, yellow |
Z = 8 | 0.35 × 0.35 × 0.30 mm |
F(000) = 1088 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 68.0°, θmin = 4.2° |
Graphite monochromator | h = −1→25 |
non–profiled ω/2θ scans | k = 0→12 |
2698 measured reflections | l = −15→0 |
2558 independent reflections | 2 standard reflections every 120 min |
2404 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.204 | w = 1/[σ2(Fo2) + (0.1659P)2 + 0.0648P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max = 0.005 |
2558 reflections | Δρmax = 0.39 e Å−3 |
332 parameters | Δρmin = −0.40 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.054 (4) |
Special details top
Experimental. IR (KBr): νmaxcm-1 3250, 1726, 1677, 1628. 1H NMR (CDCl3): 1.14–1.42
(6H, m) 1.62 (3H, s); 1.63 (3H, s); 1.74 (2H, m);
1.92 (2H, m); 3.3 (1H, m); 8.1 (1H, d, J = 16.2 Hz); 9.5
(1H, br s). 13C NMR (CDCl3): 24.2 (2CH2); 24.7 (CH2); 26.7
(2CH3); 33.1 (2CH2); 58.8 (CH);83.7 (C); 104.3 (C); 157.3 (CH); 163.9 (C);
165.4 (C). |
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 | Uiso*/Ueq | |
N1A | 0.07901 (14) | 0.9303 (3) | −0.0891 (3) | 0.0495 (7) | |
H1A | 0.088 (2) | 1.001 (5) | −0.066 (5) | 0.059* | |
C2A | 0.11756 (16) | 0.8316 (3) | −0.0827 (3) | 0.0473 (8) | |
H2A | 0.1030 | 0.7541 | −0.1133 | 0.057* | |
C3A | 0.17741 (16) | 0.8262 (3) | −0.0366 (3) | 0.0467 (8) | |
C4A | 0.21172 (19) | 0.7040 (3) | −0.0434 (3) | 0.0513 (8) | |
O5A | 0.26855 (12) | 0.6983 (3) | 0.0115 (2) | 0.0593 (8) | |
C6A | 0.2775 (2) | 0.7897 (4) | 0.0979 (4) | 0.0577 (9) | |
O7A | 0.26313 (12) | 0.9199 (2) | 0.0625 (3) | 0.0590 (8) | |
C8A | 0.20557 (17) | 0.9381 (3) | 0.0133 (3) | 0.0475 (8) | |
O9A | 0.19640 (14) | 0.6086 (2) | −0.0943 (3) | 0.0623 (7) | |
O10A | 0.18292 (13) | 1.0480 (2) | 0.0127 (3) | 0.0600 (8) | |
C11A | 0.2362 (3) | 0.7540 (5) | 0.1915 (4) | 0.0712 (13) | |
H11A | 0.2428 | 0.8159 | 0.2481 | 0.107* | |
H11B | 0.2472 | 0.6679 | 0.2160 | 0.107* | |
H11C | 0.1920 | 0.7554 | 0.1702 | 0.107* | |
C12A | 0.3485 (2) | 0.7868 (6) | 0.1229 (6) | 0.0900 (18) | |
H12A | 0.3574 | 0.8464 | 0.1802 | 0.135* | |
H12B | 0.3722 | 0.8122 | 0.0607 | 0.135* | |
H12C | 0.3606 | 0.6999 | 0.1437 | 0.135* | |
C13A | 0.01397 (17) | 0.9206 (4) | −0.1329 (4) | 0.0523 (9) | |
H13A | 0.0090 | 0.8330 | −0.1636 | 0.063* | |
C14A | 0.0033 (2) | 1.0202 (5) | −0.2222 (4) | 0.0627 (10) | |
H14A | 0.0108 | 1.1076 | −0.1947 | 0.075* | |
H14B | 0.0336 | 1.0042 | −0.2793 | 0.075* | |
C15A | −0.0645 (2) | 1.0121 (6) | −0.2666 (5) | 0.0791 (14) | |
H15A | −0.0709 | 1.0816 | −0.3183 | 0.095* | |
H15B | −0.0701 | 0.9292 | −0.3031 | 0.095* | |
C16A | −0.1135 (2) | 1.0240 (5) | −0.1798 (5) | 0.0735 (13) | |
H16A | −0.1557 | 1.0109 | −0.2102 | 0.088* | |
H16B | −0.1119 | 1.1118 | −0.1505 | 0.088* | |
C17A | −0.10330 (19) | 0.9266 (4) | −0.0909 (6) | 0.0729 (13) | |
H17A | −0.1103 | 0.8388 | −0.1180 | 0.088* | |
H17B | −0.1343 | 0.9425 | −0.0346 | 0.088* | |
C18A | −0.03584 (19) | 0.9362 (4) | −0.0446 (4) | 0.0596 (10) | |
H18A | −0.0304 | 1.0205 | −0.0101 | 0.071* | |
H18B | −0.0298 | 0.8686 | 0.0088 | 0.071* | |
N1B | 0.16831 (14) | 0.3317 (3) | 0.0951 (3) | 0.0502 (7) | |
H1B | 0.160 (2) | 0.265 (5) | 0.070 (5) | 0.060* | |
C2B | 0.13097 (15) | 0.4304 (3) | 0.0815 (3) | 0.0452 (7) | |
H2B | 0.1453 | 0.5094 | 0.1095 | 0.054* | |
C3B | 0.07215 (15) | 0.4338 (3) | 0.0305 (3) | 0.0444 (7) | |
C4B | 0.03812 (18) | 0.5566 (3) | 0.0296 (3) | 0.0473 (8) | |
O5B | −0.01668 (13) | 0.5601 (2) | −0.0301 (2) | 0.0567 (7) | |
C6B | −0.0233 (2) | 0.4645 (4) | −0.1126 (4) | 0.0577 (9) | |
O7B | −0.01107 (12) | 0.3353 (2) | −0.0712 (3) | 0.0590 (8) | |
C8B | 0.04475 (16) | 0.3189 (3) | −0.0150 (3) | 0.0475 (8) | |
O9B | 0.05280 (14) | 0.6548 (2) | 0.0782 (2) | 0.0602 (7) | |
O10B | 0.06518 (13) | 0.2093 (2) | −0.0062 (3) | 0.0647 (8) | |
C11B | 0.0209 (3) | 0.4950 (5) | −0.2039 (4) | 0.0687 (12) | |
H11D | 0.0117 | 0.5810 | −0.2306 | 0.103* | |
H11E | 0.0147 | 0.4320 | −0.2598 | 0.103* | |
H11F | 0.0644 | 0.4916 | −0.1795 | 0.103* | |
C12B | −0.0943 (2) | 0.4631 (5) | −0.1418 (6) | 0.0821 (15) | |
H12D | −0.1062 | 0.5467 | −0.1706 | 0.123* | |
H12E | −0.1192 | 0.4455 | −0.0791 | 0.123* | |
H12F | −0.1020 | 0.3963 | −0.1942 | 0.123* | |
C13B | 0.23165 (16) | 0.3427 (3) | 0.1456 (3) | 0.0509 (9) | |
H13B | 0.2354 | 0.4308 | 0.1759 | 0.061* | |
C14B | 0.23813 (19) | 0.2454 (5) | 0.2361 (4) | 0.0680 (11) | |
H14C | 0.2321 | 0.1574 | 0.2088 | 0.082* | |
H14D | 0.2053 | 0.2620 | 0.2892 | 0.082* | |
C15B | 0.3042 (3) | 0.2562 (6) | 0.2881 (4) | 0.0798 (14) | |
H15C | 0.3087 | 0.3415 | 0.3212 | 0.096* | |
H15D | 0.3083 | 0.1904 | 0.3435 | 0.096* | |
C16B | 0.3558 (2) | 0.2379 (5) | 0.2079 (5) | 0.0754 (14) | |
H16C | 0.3536 | 0.1497 | 0.1794 | 0.091* | |
H16D | 0.3970 | 0.2485 | 0.2422 | 0.091* | |
C17B | 0.34977 (19) | 0.3359 (5) | 0.1166 (5) | 0.0731 (13) | |
H17C | 0.3828 | 0.3189 | 0.0640 | 0.088* | |
H17D | 0.3560 | 0.4237 | 0.1440 | 0.088* | |
C18B | 0.28388 (17) | 0.3263 (4) | 0.0634 (4) | 0.0588 (10) | |
H18C | 0.2799 | 0.3937 | 0.0092 | 0.071* | |
H18D | 0.2795 | 0.2419 | 0.0288 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0431 (14) | 0.0440 (14) | 0.0615 (18) | −0.0020 (10) | −0.0115 (14) | −0.0049 (14) |
C2A | 0.0505 (17) | 0.0438 (15) | 0.0476 (17) | −0.0062 (12) | −0.0001 (14) | −0.0007 (14) |
C3A | 0.0505 (17) | 0.0419 (15) | 0.0476 (17) | −0.0004 (12) | 0.0011 (14) | 0.0029 (13) |
C4A | 0.0617 (19) | 0.0454 (17) | 0.0468 (18) | 0.0046 (14) | 0.0063 (16) | 0.0023 (15) |
O5A | 0.0562 (15) | 0.0556 (14) | 0.0662 (17) | 0.0143 (10) | −0.0013 (13) | −0.0043 (13) |
C6A | 0.060 (2) | 0.0477 (18) | 0.065 (2) | 0.0036 (15) | −0.0111 (19) | 0.0010 (17) |
O7A | 0.0502 (14) | 0.0463 (12) | 0.0804 (19) | 0.0003 (9) | −0.0167 (14) | 0.0038 (13) |
C8A | 0.0478 (16) | 0.0427 (16) | 0.0520 (19) | −0.0028 (12) | −0.0019 (15) | 0.0060 (14) |
O9A | 0.0796 (17) | 0.0456 (13) | 0.0616 (15) | 0.0024 (11) | −0.0007 (15) | −0.0071 (12) |
O10A | 0.0594 (14) | 0.0407 (12) | 0.0800 (19) | 0.0027 (9) | −0.0162 (14) | −0.0005 (13) |
C11A | 0.097 (3) | 0.063 (2) | 0.053 (2) | 0.008 (2) | −0.011 (2) | 0.0025 (19) |
C12A | 0.068 (3) | 0.083 (3) | 0.120 (5) | 0.013 (2) | −0.037 (3) | −0.002 (3) |
C13A | 0.0442 (17) | 0.0479 (16) | 0.065 (2) | −0.0046 (12) | −0.0122 (16) | −0.0073 (16) |
C14A | 0.057 (2) | 0.077 (3) | 0.055 (2) | −0.0041 (18) | −0.0084 (17) | 0.001 (2) |
C15A | 0.076 (3) | 0.087 (3) | 0.075 (3) | 0.000 (2) | −0.034 (3) | 0.002 (3) |
C16A | 0.050 (2) | 0.070 (2) | 0.100 (4) | −0.0002 (17) | −0.019 (2) | 0.006 (3) |
C17A | 0.0453 (19) | 0.068 (2) | 0.106 (4) | −0.0081 (15) | −0.008 (2) | 0.011 (3) |
C18A | 0.053 (2) | 0.062 (2) | 0.064 (2) | −0.0094 (15) | −0.0067 (19) | 0.0111 (18) |
N1B | 0.0419 (14) | 0.0465 (14) | 0.0622 (18) | −0.0026 (11) | −0.0050 (13) | −0.0046 (14) |
C2B | 0.0452 (16) | 0.0425 (14) | 0.0480 (17) | −0.0040 (11) | 0.0018 (14) | −0.0017 (13) |
C3B | 0.0418 (15) | 0.0427 (15) | 0.0488 (17) | −0.0001 (11) | 0.0030 (14) | 0.0027 (13) |
C4B | 0.0540 (17) | 0.0445 (17) | 0.0434 (17) | 0.0031 (13) | 0.0080 (15) | 0.0026 (14) |
O5B | 0.0545 (14) | 0.0549 (15) | 0.0605 (15) | 0.0182 (10) | −0.0048 (12) | −0.0042 (12) |
C6B | 0.062 (2) | 0.0499 (18) | 0.062 (2) | 0.0128 (15) | −0.0143 (18) | −0.0029 (17) |
O7B | 0.0491 (13) | 0.0498 (13) | 0.0782 (19) | 0.0013 (9) | −0.0155 (13) | 0.0011 (13) |
C8B | 0.0451 (15) | 0.0429 (15) | 0.0544 (18) | 0.0021 (12) | −0.0037 (14) | 0.0016 (15) |
O9B | 0.0796 (17) | 0.0442 (13) | 0.0567 (15) | 0.0042 (10) | 0.0032 (15) | −0.0069 (12) |
O10B | 0.0648 (15) | 0.0402 (12) | 0.089 (2) | 0.0048 (10) | −0.0246 (15) | −0.0048 (14) |
C11B | 0.083 (3) | 0.071 (3) | 0.052 (2) | 0.008 (2) | −0.006 (2) | −0.0025 (18) |
C12B | 0.061 (2) | 0.084 (3) | 0.101 (4) | 0.020 (2) | −0.026 (3) | −0.002 (3) |
C13B | 0.0436 (18) | 0.0478 (16) | 0.061 (2) | −0.0032 (12) | −0.0054 (16) | −0.0023 (16) |
C14B | 0.059 (2) | 0.089 (3) | 0.055 (2) | −0.011 (2) | −0.0010 (18) | 0.014 (2) |
C15B | 0.083 (3) | 0.099 (4) | 0.057 (2) | −0.003 (3) | −0.025 (2) | 0.012 (2) |
C16B | 0.051 (2) | 0.068 (2) | 0.107 (4) | 0.0081 (17) | −0.028 (2) | 0.000 (3) |
C17B | 0.0424 (19) | 0.086 (3) | 0.091 (3) | −0.0050 (17) | −0.006 (2) | 0.010 (3) |
C18B | 0.0422 (17) | 0.074 (2) | 0.060 (2) | −0.0055 (16) | −0.0018 (17) | 0.012 (2) |
Geometric parameters (Å, º) top
N1A—C2A | 1.294 (4) | N1B—C2B | 1.287 (5) |
N1A—C13A | 1.469 (4) | N1B—C13B | 1.472 (4) |
N1A—H1A | 0.80 (5) | N1B—H1B | 0.77 (5) |
C2A—C3A | 1.379 (5) | C2B—C3B | 1.386 (5) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C8A | 1.430 (5) | C3B—C8B | 1.425 (5) |
C3A—C4A | 1.443 (5) | C3B—C4B | 1.443 (4) |
C4A—O9A | 1.208 (5) | C4B—O9B | 1.213 (4) |
C4A—O5A | 1.373 (5) | C4B—O5B | 1.368 (5) |
O5A—C6A | 1.441 (5) | O5B—C6B | 1.429 (5) |
C6A—O7A | 1.435 (4) | C6B—O7B | 1.441 (5) |
C6A—C11A | 1.501 (7) | C6B—C11B | 1.501 (7) |
C6A—C12A | 1.516 (6) | C6B—C12B | 1.528 (6) |
O7A—C8A | 1.364 (4) | O7B—C8B | 1.373 (4) |
C8A—O10A | 1.219 (4) | C8B—O10B | 1.204 (4) |
C11A—H11A | 0.9600 | C11B—H11D | 0.9600 |
C11A—H11B | 0.9600 | C11B—H11E | 0.9600 |
C11A—H11C | 0.9600 | C11B—H11F | 0.9600 |
C12A—H12A | 0.9600 | C12B—H12D | 0.9600 |
C12A—H12B | 0.9600 | C12B—H12E | 0.9600 |
C12A—H12C | 0.9600 | C12B—H12F | 0.9600 |
C13A—C18A | 1.527 (6) | C13B—C18B | 1.510 (5) |
C13A—C14A | 1.528 (6) | C13B—C14B | 1.513 (6) |
C13A—H13A | 0.9800 | C13B—H13B | 0.9800 |
C14A—C15A | 1.525 (6) | C14B—C15B | 1.532 (6) |
C14A—H14A | 0.9700 | C14B—H14C | 0.9700 |
C14A—H14B | 0.9700 | C14B—H14D | 0.9700 |
C15A—C16A | 1.496 (8) | C15B—C16B | 1.484 (8) |
C15A—H15A | 0.9700 | C15B—H15C | 0.9700 |
C15A—H15B | 0.9700 | C15B—H15D | 0.9700 |
C16A—C17A | 1.509 (8) | C16B—C17B | 1.524 (8) |
C16A—H16A | 0.9700 | C16B—H16C | 0.9700 |
C16A—H16B | 0.9700 | C16B—H16D | 0.9700 |
C17A—C18A | 1.528 (5) | C17B—C18B | 1.533 (6) |
C17A—H17A | 0.9700 | C17B—H17C | 0.9700 |
C17A—H17B | 0.9700 | C17B—H17D | 0.9700 |
C18A—H18A | 0.9700 | C18B—H18C | 0.9700 |
C18A—H18B | 0.9700 | C18B—H18D | 0.9700 |
| | | |
C2A—N1A—C13A | 123.1 (3) | C2B—N1B—C13B | 122.8 (3) |
C2A—N1A—H1A | 122 (3) | C2B—N1B—H1B | 120 (4) |
C13A—N1A—H1A | 114 (3) | C13B—N1B—H1B | 117 (3) |
N1A—C2A—C3A | 128.5 (3) | N1B—C2B—C3B | 128.2 (3) |
N1A—C2A—H2A | 115.8 | N1B—C2B—H2B | 115.9 |
C3A—C2A—H2A | 115.8 | C3B—C2B—H2B | 115.9 |
C2A—C3A—C8A | 121.6 (3) | C2B—C3B—C8B | 121.3 (3) |
C2A—C3A—C4A | 117.4 (3) | C2B—C3B—C4B | 117.6 (3) |
C8A—C3A—C4A | 120.9 (3) | C8B—C3B—C4B | 121.1 (3) |
O9A—C4A—O5A | 117.3 (3) | O9B—C4B—O5B | 117.7 (3) |
O9A—C4A—C3A | 126.7 (4) | O9B—C4B—C3B | 126.2 (3) |
O5A—C4A—C3A | 115.9 (3) | O5B—C4B—C3B | 116.1 (3) |
C4A—O5A—C6A | 117.4 (3) | C4B—O5B—C6B | 117.3 (3) |
O7A—C6A—O5A | 110.1 (3) | O5B—C6B—O7B | 110.4 (3) |
O7A—C6A—C11A | 110.2 (4) | O5B—C6B—C11B | 110.3 (4) |
O5A—C6A—C11A | 110.7 (3) | O7B—C6B—C11B | 110.8 (3) |
O7A—C6A—C12A | 106.7 (4) | O5B—C6B—C12B | 105.9 (4) |
O5A—C6A—C12A | 105.6 (4) | O7B—C6B—C12B | 104.5 (4) |
C11A—C6A—C12A | 113.4 (5) | C11B—C6B—C12B | 114.7 (4) |
C8A—O7A—C6A | 116.8 (3) | C8B—O7B—C6B | 116.6 (3) |
O10A—C8A—O7A | 118.1 (3) | O10B—C8B—O7B | 117.5 (3) |
O10A—C8A—C3A | 125.1 (3) | O10B—C8B—C3B | 126.0 (3) |
O7A—C8A—C3A | 116.8 (3) | O7B—C8B—C3B | 116.4 (3) |
C6A—C11A—H11A | 109.5 | C6B—C11B—H11D | 109.5 |
C6A—C11A—H11B | 109.5 | C6B—C11B—H11E | 109.5 |
H11A—C11A—H11B | 109.5 | H11D—C11B—H11E | 109.5 |
C6A—C11A—H11C | 109.5 | C6B—C11B—H11F | 109.5 |
H11A—C11A—H11C | 109.5 | H11D—C11B—H11F | 109.5 |
H11B—C11A—H11C | 109.5 | H11E—C11B—H11F | 109.5 |
C6A—C12A—H12A | 109.5 | C6B—C12B—H12D | 109.5 |
C6A—C12A—H12B | 109.5 | C6B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C6A—C12A—H12C | 109.5 | C6B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
N1A—C13A—C18A | 110.7 (3) | N1B—C13B—C18B | 110.4 (3) |
N1A—C13A—C14A | 111.3 (3) | N1B—C13B—C14B | 110.6 (3) |
C18A—C13A—C14A | 111.1 (3) | C18B—C13B—C14B | 111.8 (3) |
N1A—C13A—H13A | 107.9 | N1B—C13B—H13B | 107.9 |
C18A—C13A—H13A | 107.9 | C18B—C13B—H13B | 107.9 |
C14A—C13A—H13A | 107.9 | C14B—C13B—H13B | 107.9 |
C15A—C14A—C13A | 111.5 (4) | C13B—C14B—C15B | 110.6 (4) |
C15A—C14A—H14A | 109.3 | C13B—C14B—H14C | 109.5 |
C13A—C14A—H14A | 109.3 | C15B—C14B—H14C | 109.5 |
C15A—C14A—H14B | 109.3 | C13B—C14B—H14D | 109.5 |
C13A—C14A—H14B | 109.3 | C15B—C14B—H14D | 109.5 |
H14A—C14A—H14B | 108.0 | H14C—C14B—H14D | 108.1 |
C16A—C15A—C14A | 111.5 (4) | C16B—C15B—C14B | 111.0 (4) |
C16A—C15A—H15A | 109.3 | C16B—C15B—H15C | 109.4 |
C14A—C15A—H15A | 109.3 | C14B—C15B—H15C | 109.4 |
C16A—C15A—H15B | 109.3 | C16B—C15B—H15D | 109.4 |
C14A—C15A—H15B | 109.3 | C14B—C15B—H15D | 109.4 |
H15A—C15A—H15B | 108.0 | H15C—C15B—H15D | 108.0 |
C15A—C16A—C17A | 112.7 (4) | C15B—C16B—C17B | 111.4 (4) |
C15A—C16A—H16A | 109.1 | C15B—C16B—H16C | 109.4 |
C17A—C16A—H16A | 109.1 | C17B—C16B—H16C | 109.4 |
C15A—C16A—H16B | 109.1 | C15B—C16B—H16D | 109.4 |
C17A—C16A—H16B | 109.1 | C17B—C16B—H16D | 109.4 |
H16A—C16A—H16B | 107.8 | H16C—C16B—H16D | 108.0 |
C16A—C17A—C18A | 111.5 (4) | C16B—C17B—C18B | 110.9 (4) |
C16A—C17A—H17A | 109.3 | C16B—C17B—H17C | 109.5 |
C18A—C17A—H17A | 109.3 | C18B—C17B—H17C | 109.5 |
C16A—C17A—H17B | 109.3 | C16B—C17B—H17D | 109.5 |
C18A—C17A—H17B | 109.3 | C18B—C17B—H17D | 109.5 |
H17A—C17A—H17B | 108.0 | H17C—C17B—H17D | 108.0 |
C13A—C18A—C17A | 110.4 (4) | C13B—C18B—C17B | 110.3 (4) |
C13A—C18A—H18A | 109.6 | C13B—C18B—H18C | 109.6 |
C17A—C18A—H18A | 109.6 | C17B—C18B—H18C | 109.6 |
C13A—C18A—H18B | 109.6 | C13B—C18B—H18D | 109.6 |
C17A—C18A—H18B | 109.6 | C17B—C18B—H18D | 109.6 |
H18A—C18A—H18B | 108.1 | H18C—C18B—H18D | 108.1 |
| | | |
C13A—N1A—C2A—C3A | −174.8 (4) | C13B—N1B—C2B—C3B | 176.4 (4) |
N1A—C2A—C3A—C8A | 0.0 (6) | N1B—C2B—C3B—C8B | 0.5 (6) |
N1A—C2A—C3A—C4A | −178.0 (4) | N1B—C2B—C3B—C4B | 177.5 (4) |
C2A—C3A—C4A—O9A | 7.8 (6) | C2B—C3B—C4B—O9B | −7.8 (5) |
C8A—C3A—C4A—O9A | −170.3 (4) | C8B—C3B—C4B—O9B | 169.2 (4) |
C2A—C3A—C4A—O5A | −174.4 (3) | C2B—C3B—C4B—O5B | 173.9 (3) |
C8A—C3A—C4A—O5A | 7.5 (5) | C8B—C3B—C4B—O5B | −9.1 (5) |
O9A—C4A—O5A—C6A | −160.2 (4) | O9B—C4B—O5B—C6B | 160.1 (4) |
C3A—C4A—O5A—C6A | 21.7 (5) | C3B—C4B—O5B—C6B | −21.4 (4) |
C4A—O5A—C6A—O7A | −50.4 (4) | C4B—O5B—C6B—O7B | 50.6 (4) |
C4A—O5A—C6A—C11A | 71.7 (4) | C4B—O5B—C6B—C11B | −72.3 (4) |
C4A—O5A—C6A—C12A | −165.1 (4) | C4B—O5B—C6B—C12B | 163.1 (4) |
O5A—C6A—O7A—C8A | 51.7 (5) | O5B—C6B—O7B—C8B | −51.2 (5) |
C11A—C6A—O7A—C8A | −70.6 (5) | C11B—C6B—O7B—C8B | 71.4 (4) |
C12A—C6A—O7A—C8A | 165.9 (4) | C12B—C6B—O7B—C8B | −164.6 (4) |
C6A—O7A—C8A—O10A | 157.2 (4) | C6B—O7B—C8B—O10B | −159.2 (4) |
C6A—O7A—C8A—C3A | −24.6 (5) | C6B—O7B—C8B—C3B | 22.7 (5) |
C2A—C3A—C8A—O10A | −6.1 (6) | C2B—C3B—C8B—O10B | 7.2 (6) |
C4A—C3A—C8A—O10A | 171.9 (4) | C4B—C3B—C8B—O10B | −169.7 (4) |
C2A—C3A—C8A—O7A | 175.9 (3) | C2B—C3B—C8B—O7B | −174.8 (3) |
C4A—C3A—C8A—O7A | −6.1 (5) | C4B—C3B—C8B—O7B | 8.3 (5) |
C2A—N1A—C13A—C18A | 110.1 (4) | C2B—N1B—C13B—C18B | −108.3 (4) |
C2A—N1A—C13A—C14A | −125.9 (4) | C2B—N1B—C13B—C14B | 127.4 (4) |
N1A—C13A—C14A—C15A | −179.0 (4) | N1B—C13B—C14B—C15B | 179.5 (4) |
C18A—C13A—C14A—C15A | −55.1 (5) | C18B—C13B—C14B—C15B | 56.0 (5) |
C13A—C14A—C15A—C16A | 53.9 (6) | C13B—C14B—C15B—C16B | −56.4 (6) |
C14A—C15A—C16A—C17A | −53.9 (6) | C14B—C15B—C16B—C17B | 56.9 (6) |
C15A—C16A—C17A—C18A | 55.0 (6) | C15B—C16B—C17B—C18B | −56.5 (6) |
N1A—C13A—C18A—C17A | 179.8 (3) | N1B—C13B—C18B—C17B | −179.2 (3) |
C14A—C13A—C18A—C17A | 55.6 (4) | C14B—C13B—C18B—C17B | −55.6 (5) |
C16A—C17A—C18A—C13A | −55.3 (5) | C16B—C17B—C18B—C13B | 55.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O10A | 0.80 (5) | 2.27 (5) | 2.791 (4) | 124 (4) |
N1B—H1B···O10B | 0.77 (5) | 2.27 (5) | 2.796 (4) | 126 (4) |
N1A—H1A···O10Bi | 0.80 (5) | 2.31 (5) | 3.049 (4) | 154 (4) |
N1B—H1B···O10Aii | 0.77 (5) | 2.38 (5) | 3.093 (4) | 154 (4) |
C15B—H15D···O10Aiii | 0.97 | 2.58 | 3.536 (6) | 170 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1/2, y−1, z+1/2. |