In the title compound, C
25H
27N
3O·0.25H
2O, the minimum and maximum C—C bond lengths in the cyclopentane ring are 1.444 (3) and 1.489 (3) Å, respectively. In the crystal structure, molecules are linked by weak intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 242029
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.056
- wR factor = 0.118
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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
1 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
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1'-biphenyl-
2-carbonitrile–water (4/1)
top
Crystal data top
C25H27N3O·0.25H2O | Z = 2 |
Mr = 390.00 | F(000) = 417 |
Triclinic, P1 | Dx = 1.201 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1419 (13) Å | Cell parameters from 831 reflections |
b = 10.0656 (14) Å | θ = 2.5–21.4° |
c = 12.1721 (17) Å | µ = 0.08 mm−1 |
α = 90.438 (3)° | T = 293 K |
β = 105.110 (3)° | Prism, colorless |
γ = 94.126 (3)° | 0.32 × 0.28 × 0.20 mm |
V = 1078.1 (3) Å3 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 3713 independent reflections |
Radiation source: fine-focus sealed tube | 3033 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→10 |
Tmin = 0.97, Tmax = 0.98 | k = −11→11 |
5382 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3 |
3713 reflections | (Δ/σ)max < 0.001 |
301 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
Special details top
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 | Occ. (<1) |
O1 | 0.37120 (14) | 0.35422 (13) | 0.40617 (10) | 0.0532 (3) | |
N1 | 0.52565 (16) | 0.37240 (14) | 0.28629 (12) | 0.0453 (3) | |
N2 | 0.39725 (17) | 0.24482 (14) | 0.13523 (13) | 0.0472 (4) | |
N3 | 1.06784 (19) | 0.38612 (17) | 0.85448 (15) | 0.0560 (4) | |
C1 | 0.6525 (2) | 0.45808 (18) | 0.35922 (16) | 0.0502 (4) | |
H1A | 0.6129 | 0.5131 | 0.4089 | 0.060* | |
H1B | 0.6959 | 0.5170 | 0.3113 | 0.060* | |
C2 | 0.77747 (18) | 0.37985 (17) | 0.43166 (14) | 0.0437 (4) | |
C3 | 0.75036 (19) | 0.31504 (18) | 0.52482 (15) | 0.0480 (4) | |
H3 | 0.6567 | 0.3187 | 0.5410 | 0.058* | |
C4 | 0.86288 (19) | 0.24395 (18) | 0.59507 (16) | 0.0485 (4) | |
H4 | 0.8451 | 0.2005 | 0.6581 | 0.058* | |
C5 | 0.99929 (19) | 0.23956 (16) | 0.56934 (14) | 0.0413 (4) | |
C6 | 1.0261 (2) | 0.30255 (17) | 0.47521 (15) | 0.0464 (4) | |
H6 | 1.1189 | 0.2979 | 0.4579 | 0.056* | |
C7 | 0.9140 (2) | 0.37220 (17) | 0.40729 (16) | 0.0483 (4) | |
H7 | 0.9317 | 0.4146 | 0.3439 | 0.058* | |
C8 | 1.1098 (2) | 0.16348 (17) | 0.64605 (15) | 0.0472 (4) | |
C9 | 1.1533 (2) | 0.18984 (17) | 0.76350 (15) | 0.0458 (4) | |
C10 | 1.2592 (2) | 0.11897 (19) | 0.83336 (17) | 0.0526 (5) | |
H10A | 1.2848 | 0.1358 | 0.9115 | 0.063* | |
C11 | 1.3283 (2) | 0.0237 (2) | 0.78982 (18) | 0.0551 (5) | |
H11A | 1.4005 | −0.0240 | 0.8386 | 0.066* | |
C12 | 1.2926 (2) | −0.00268 (19) | 0.67504 (18) | 0.0559 (5) | |
H12A | 1.3331 | −0.0738 | 0.6472 | 0.067* | |
C13 | 1.1821 (2) | 0.06690 (18) | 0.60405 (16) | 0.0504 (4) | |
H13A | 1.1559 | 0.0481 | 0.5261 | 0.060* | |
C14 | 1.1076 (2) | 0.30021 (19) | 0.81408 (16) | 0.0486 (4) | |
C15 | 0.51656 (18) | 0.32003 (16) | 0.17759 (14) | 0.0395 (4) | |
C16 | 0.30514 (19) | 0.24000 (17) | 0.21733 (15) | 0.0440 (4) | |
C17 | 0.3814 (2) | 0.33082 (18) | 0.31310 (16) | 0.0495 (4) | |
C18 | 0.15181 (19) | 0.2832 (2) | 0.18066 (17) | 0.0533 (5) | |
H18A | 0.1466 | 0.3518 | 0.1245 | 0.064* | |
H18B | 0.1216 | 0.3190 | 0.2449 | 0.064* | |
C19 | 0.0506 (2) | 0.16347 (18) | 0.13041 (19) | 0.0605 (5) | |
H19A | −0.0387 | 0.1581 | 0.1596 | 0.073* | |
H19B | 0.0175 | 0.1703 | 0.0483 | 0.073* | |
C20 | 0.1314 (2) | 0.0452 (2) | 0.1591 (2) | 0.0624 (5) | |
H20A | 0.1596 | 0.0080 | 0.0944 | 0.075* | |
H20B | 0.0738 | −0.0225 | 0.1901 | 0.075* | |
C21 | 0.2639 (2) | 0.10385 (18) | 0.24555 (17) | 0.0526 (4) | |
H21A | 0.2412 | 0.1045 | 0.3191 | 0.063* | |
H21B | 0.3491 | 0.0499 | 0.2507 | 0.063* | |
C22 | 0.6418 (2) | 0.35770 (18) | 0.12222 (16) | 0.0482 (4) | |
H22A | 0.7338 | 0.3186 | 0.1630 | 0.058* | 0.832 (10) |
H22B | 0.6623 | 0.4538 | 0.1264 | 0.058* | 0.832 (10) |
C23 | 0.5983 (5) | 0.3089 (4) | −0.0045 (3) | 0.0444 (8) | 0.832 (10) |
H23A | 0.5983 | 0.2126 | −0.0081 | 0.053* | 0.832 (10) |
H23B | 0.4965 | 0.3326 | −0.0414 | 0.053* | 0.832 (10) |
C24 | 0.7061 (5) | 0.3687 (3) | −0.0660 (3) | 0.0461 (8) | 0.832 (10) |
H24A | 0.8073 | 0.3429 | −0.0299 | 0.055* | 0.832 (10) |
H24B | 0.7085 | 0.4650 | −0.0597 | 0.055* | 0.832 (10) |
C25 | 0.6649 (8) | 0.3269 (6) | −0.1915 (6) | 0.0436 (12) | 0.832 (10) |
H25A | 0.6972 | 0.2394 | −0.1993 | 0.065* | 0.832 (10) |
H25B | 0.7147 | 0.3890 | −0.2320 | 0.065* | 0.832 (10) |
H25C | 0.5569 | 0.3258 | −0.2223 | 0.065* | 0.832 (10) |
H22C | 0.7376 | 0.3551 | 0.1797 | 0.058* | 0.168 (10) |
H22D | 0.6328 | 0.4495 | 0.0994 | 0.058* | 0.168 (10) |
C23' | 0.652 (2) | 0.2727 (14) | 0.0161 (14) | 0.044 (4) | 0.168 (10) |
H23C | 0.5734 | 0.1998 | 0.0007 | 0.053* | 0.168 (10) |
H23D | 0.7499 | 0.2354 | 0.0311 | 0.053* | 0.168 (10) |
C25' | 0.632 (4) | 0.297 (3) | −0.206 (3) | 0.030 (4) | 0.168 (10) |
H25D | 0.6691 | 0.2102 | −0.1900 | 0.045* | 0.168 (10) |
H25E | 0.6981 | 0.3483 | −0.2425 | 0.045* | 0.168 (10) |
H25F | 0.5314 | 0.2875 | −0.2559 | 0.045* | 0.168 (10) |
C24' | 0.630 (3) | 0.3685 (13) | −0.0937 (12) | 0.046 (4) | 0.168 (10) |
H24C | 0.5336 | 0.4083 | −0.1049 | 0.055* | 0.168 (10) |
H24D | 0.7098 | 0.4402 | −0.0768 | 0.055* | 0.168 (10) |
O1W | 0.5006 (6) | 0.0870 (5) | 0.4997 (4) | 0.0515 (12) | 0.25 |
H1WC | 0.4595 | 0.0287 | 0.4478 | 0.062* | 0.25 |
H1WB | 0.4349 | 0.1102 | 0.5328 | 0.062* | 0.25 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0520 (7) | 0.0646 (7) | 0.0430 (7) | −0.0001 (6) | 0.0136 (6) | −0.0054 (6) |
N1 | 0.0445 (8) | 0.0501 (8) | 0.0412 (8) | 0.0040 (6) | 0.0113 (6) | −0.0010 (6) |
N2 | 0.0498 (8) | 0.0490 (8) | 0.0445 (8) | −0.0017 (6) | 0.0166 (6) | 0.0025 (7) |
N3 | 0.0503 (8) | 0.0558 (9) | 0.0587 (10) | 0.0060 (7) | 0.0081 (7) | −0.0032 (8) |
C1 | 0.0520 (10) | 0.0541 (10) | 0.0457 (10) | −0.0003 (8) | 0.0164 (8) | −0.0008 (8) |
C2 | 0.0430 (9) | 0.0493 (9) | 0.0378 (9) | −0.0058 (7) | 0.0115 (7) | 0.0011 (7) |
C3 | 0.0372 (9) | 0.0586 (10) | 0.0473 (10) | 0.0023 (8) | 0.0095 (8) | 0.0001 (8) |
C4 | 0.0445 (9) | 0.0566 (10) | 0.0441 (10) | 0.0040 (8) | 0.0108 (8) | −0.0011 (8) |
C5 | 0.0484 (9) | 0.0351 (8) | 0.0408 (9) | 0.0027 (7) | 0.0126 (7) | −0.0014 (7) |
C6 | 0.0500 (10) | 0.0482 (9) | 0.0439 (9) | 0.0040 (8) | 0.0175 (8) | −0.0029 (7) |
C7 | 0.0518 (10) | 0.0446 (9) | 0.0511 (10) | 0.0051 (8) | 0.0178 (8) | 0.0011 (8) |
C8 | 0.0505 (10) | 0.0480 (9) | 0.0456 (10) | 0.0018 (8) | 0.0176 (8) | 0.0025 (7) |
C9 | 0.0478 (9) | 0.0433 (8) | 0.0472 (10) | 0.0010 (7) | 0.0149 (8) | 0.0046 (8) |
C10 | 0.0550 (10) | 0.0573 (11) | 0.0462 (10) | −0.0025 (9) | 0.0164 (8) | 0.0001 (9) |
C11 | 0.0482 (10) | 0.0571 (11) | 0.0591 (12) | 0.0053 (8) | 0.0119 (9) | 0.0020 (9) |
C12 | 0.0505 (11) | 0.0530 (10) | 0.0615 (12) | 0.0124 (9) | 0.0078 (9) | −0.0026 (9) |
C13 | 0.0505 (10) | 0.0548 (10) | 0.0446 (10) | 0.0100 (8) | 0.0088 (8) | −0.0011 (8) |
C14 | 0.0496 (9) | 0.0525 (10) | 0.0438 (10) | 0.0023 (8) | 0.0128 (8) | 0.0020 (8) |
C15 | 0.0380 (8) | 0.0406 (8) | 0.0407 (9) | 0.0054 (7) | 0.0109 (7) | 0.0035 (7) |
C16 | 0.0414 (9) | 0.0488 (9) | 0.0423 (9) | 0.0043 (7) | 0.0120 (7) | 0.0020 (7) |
C17 | 0.0576 (11) | 0.0500 (10) | 0.0429 (10) | 0.0052 (8) | 0.0167 (8) | 0.0004 (8) |
C18 | 0.0405 (9) | 0.0652 (11) | 0.0530 (11) | 0.0009 (8) | 0.0111 (8) | 0.0012 (9) |
C19 | 0.0529 (11) | 0.0509 (10) | 0.0677 (13) | −0.0009 (8) | −0.0008 (9) | 0.0054 (9) |
C20 | 0.0515 (11) | 0.0567 (11) | 0.0747 (14) | −0.0072 (9) | 0.0119 (10) | 0.0010 (10) |
C21 | 0.0570 (11) | 0.0487 (10) | 0.0529 (11) | 0.0045 (8) | 0.0154 (9) | 0.0077 (8) |
C22 | 0.0463 (10) | 0.0518 (10) | 0.0497 (10) | 0.0024 (8) | 0.0182 (8) | 0.0004 (8) |
C23 | 0.0577 (19) | 0.0371 (17) | 0.0381 (14) | −0.0002 (13) | 0.0128 (14) | 0.0041 (12) |
C24 | 0.0479 (18) | 0.0517 (13) | 0.0403 (17) | 0.0068 (13) | 0.0138 (14) | 0.0041 (11) |
C25 | 0.048 (3) | 0.037 (3) | 0.041 (3) | 0.0008 (18) | 0.005 (2) | 0.006 (2) |
C23' | 0.056 (8) | 0.026 (6) | 0.046 (7) | 0.027 (5) | 0.000 (6) | 0.009 (5) |
C25' | 0.041 (12) | 0.014 (8) | 0.027 (7) | −0.005 (6) | −0.004 (7) | −0.004 (6) |
C24' | 0.056 (10) | 0.034 (5) | 0.039 (7) | 0.018 (7) | −0.006 (7) | 0.009 (5) |
O1W | 0.056 (3) | 0.054 (3) | 0.041 (3) | 0.006 (2) | 0.007 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
O1—C17 | 1.184 (2) | C16—C17 | 1.466 (2) |
N1—C15 | 1.400 (2) | C18—C19 | 1.489 (3) |
N1—C17 | 1.472 (2) | C18—H18A | 0.9700 |
N1—C1 | 1.478 (2) | C18—H18B | 0.9700 |
N2—C15 | 1.269 (2) | C19—C20 | 1.444 (3) |
N2—C16 | 1.464 (2) | C19—H19A | 0.9700 |
N3—C14 | 1.119 (2) | C19—H19B | 0.9700 |
C1—C2 | 1.522 (2) | C20—C21 | 1.465 (3) |
C1—H1A | 0.9700 | C20—H20A | 0.9700 |
C1—H1B | 0.9700 | C20—H20B | 0.9700 |
C2—C7 | 1.363 (2) | C21—H21A | 0.9700 |
C2—C3 | 1.381 (2) | C21—H21B | 0.9700 |
C3—C4 | 1.399 (2) | C22—C23 | 1.555 (3) |
C3—H3 | 0.9300 | C22—H22A | 0.9700 |
C4—C5 | 1.366 (2) | C22—H22B | 0.9700 |
C4—H4 | 0.9300 | C23—C24 | 1.484 (4) |
C5—C6 | 1.382 (2) | C23—H23A | 0.9700 |
C5—C8 | 1.452 (2) | C23—H23B | 0.9700 |
C6—C7 | 1.377 (2) | C24—C25 | 1.523 (7) |
C6—H6 | 0.9300 | C24—H24A | 0.9700 |
C7—H7 | 0.9300 | C24—H24B | 0.9700 |
C8—C13 | 1.380 (3) | C25—H25A | 0.9600 |
C8—C9 | 1.398 (2) | C25—H25B | 0.9600 |
C9—C10 | 1.360 (3) | C25—H25C | 0.9600 |
C9—C14 | 1.406 (3) | C23'—C24' | 1.63 (2) |
C10—C11 | 1.361 (3) | C23'—H23C | 0.9700 |
C10—H10A | 0.9300 | C23'—H23D | 0.9700 |
C11—C12 | 1.369 (3) | C25'—C24' | 1.55 (3) |
C11—H11A | 0.9300 | C25'—H25D | 0.9600 |
C12—C13 | 1.383 (2) | C25'—H25E | 0.9600 |
C12—H12A | 0.9300 | C25'—H25F | 0.9600 |
C13—H13A | 0.9300 | C24'—H24C | 0.9700 |
C15—C22 | 1.501 (2) | C24'—H24D | 0.9700 |
C16—C18 | 1.455 (2) | O1W—H1WC | 0.8500 |
C16—C21 | 1.462 (2) | O1W—H1WB | 0.8500 |
| | | |
C15—N1—C17 | 107.06 (14) | C16—C18—H18A | 110.4 |
C15—N1—C1 | 126.97 (14) | C19—C18—H18A | 110.4 |
C17—N1—C1 | 125.92 (14) | C16—C18—H18B | 110.4 |
C15—N2—C16 | 107.76 (15) | C19—C18—H18B | 110.4 |
N1—C1—C2 | 113.35 (14) | H18A—C18—H18B | 108.6 |
N1—C1—H1A | 108.9 | C20—C19—C18 | 109.65 (16) |
C2—C1—H1A | 108.9 | C20—C19—H19A | 109.7 |
N1—C1—H1B | 108.9 | C18—C19—H19A | 109.7 |
C2—C1—H1B | 108.9 | C20—C19—H19B | 109.7 |
H1A—C1—H1B | 107.7 | C18—C19—H19B | 109.7 |
C7—C2—C3 | 119.51 (17) | H19A—C19—H19B | 108.2 |
C7—C2—C1 | 122.09 (16) | C19—C20—C21 | 98.86 (16) |
C3—C2—C1 | 118.41 (15) | C19—C20—H20A | 112.0 |
C2—C3—C4 | 120.42 (16) | C21—C20—H20A | 112.0 |
C2—C3—H3 | 119.8 | C19—C20—H20B | 112.0 |
C4—C3—H3 | 119.8 | C21—C20—H20B | 112.0 |
C5—C4—C3 | 118.72 (17) | H20A—C20—H20B | 109.7 |
C5—C4—H4 | 120.6 | C16—C21—C20 | 110.92 (16) |
C3—C4—H4 | 120.6 | C16—C21—H21A | 109.5 |
C4—C5—C6 | 121.05 (17) | C20—C21—H21A | 109.5 |
C4—C5—C8 | 115.38 (16) | C16—C21—H21B | 109.5 |
C6—C5—C8 | 123.56 (16) | C20—C21—H21B | 109.5 |
C7—C6—C5 | 119.33 (16) | H21A—C21—H21B | 108.0 |
C7—C6—H6 | 120.3 | C15—C22—C23 | 111.12 (17) |
C5—C6—H6 | 120.3 | C15—C22—H22A | 109.4 |
C2—C7—C6 | 120.96 (17) | C23—C22—H22A | 109.4 |
C2—C7—H7 | 119.5 | C15—C22—H22B | 109.4 |
C6—C7—H7 | 119.5 | C23—C22—H22B | 109.4 |
C13—C8—C9 | 117.56 (17) | H22A—C22—H22B | 108.0 |
C13—C8—C5 | 120.58 (16) | C24—C23—C22 | 111.4 (3) |
C9—C8—C5 | 121.77 (16) | C24—C23—H23A | 109.3 |
C10—C9—C8 | 120.67 (17) | C22—C23—H23A | 109.3 |
C10—C9—C14 | 116.03 (17) | C24—C23—H23B | 109.3 |
C8—C9—C14 | 122.74 (17) | C22—C23—H23B | 109.3 |
C9—C10—C11 | 120.57 (18) | H23A—C23—H23B | 108.0 |
C9—C10—H10A | 119.7 | C23—C24—C25 | 113.2 (3) |
C11—C10—H10A | 119.7 | C23—C24—H24A | 108.9 |
C10—C11—C12 | 120.74 (18) | C25—C24—H24A | 108.9 |
C10—C11—H11A | 119.6 | C23—C24—H24B | 108.9 |
C12—C11—H11A | 119.6 | C25—C24—H24B | 108.9 |
C11—C12—C13 | 118.81 (18) | H24A—C24—H24B | 107.8 |
C11—C12—H12A | 119.7 | C24'—C23'—H23C | 109.9 |
C13—C12—H12A | 121.0 | C24'—C23'—H23D | 109.9 |
C8—C13—C12 | 121.59 (18) | H23C—C23'—H23D | 108.3 |
C8—C13—H13A | 119.2 | C24'—C25'—H25D | 109.5 |
C12—C13—H13A | 119.2 | C24'—C25'—H25E | 109.5 |
N3—C14—C9 | 178.2 (2) | H25D—C25'—H25E | 109.5 |
N2—C15—N1 | 114.22 (15) | C24'—C25'—H25F | 109.5 |
N2—C15—C22 | 126.63 (16) | H25D—C25'—H25F | 109.5 |
N1—C15—C22 | 119.15 (15) | H25E—C25'—H25F | 109.5 |
C18—C16—C21 | 97.33 (15) | C25'—C24'—C23' | 114.7 (15) |
C18—C16—N2 | 117.94 (15) | C25'—C24'—H24C | 108.6 |
C21—C16—N2 | 112.73 (15) | C23'—C24'—H24C | 108.6 |
C18—C16—C17 | 104.18 (14) | C25'—C24'—H24D | 108.6 |
C21—C16—C17 | 116.59 (16) | C23'—C24'—H24D | 108.6 |
N2—C16—C17 | 107.89 (14) | H24C—C24'—H24D | 107.6 |
O1—C17—C16 | 137.42 (18) | O1Wi—O1W—H1WC | 49.4 |
O1—C17—N1 | 117.83 (16) | O1Wi—O1W—H1WB | 108.4 |
C16—C17—N1 | 102.60 (14) | H1WC—O1W—H1WB | 109.5 |
C16—C18—C19 | 106.61 (16) | | |
| | | |
C4—C5—C8—C9 | −54.7 (2) | C6—C5—C8—C13 | −50.0 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1ii | 0.97 | 2.57 | 3.474 (2) | 154 |
C6—H6···O1iii | 0.93 | 2.57 | 3.477 (2) | 164 |
C18—H18B···O1 | 0.97 | 2.59 | 2.994 (2) | 105 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z. |