The title compound, C
23H
26ClN
5O
2, was synthesized by the reaction of 4-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperazine and 5-chloromethyl-3-(2-chlorophenyl)-1,2,4-oxadiazole. In the structure, there are intramolecular C—H
N, N—H
N and C—H
O hydrogen bonds, and intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 277273
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.201
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23
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
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens,1996); software used to prepare material for publication: SHELXL97.
4-{[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl}-1-[(2,6-
dimethylphenyl)aminocarbonylmethyl]piperazine
top
Crystal data top
C23H26ClN5O2 | F(000) = 928 |
Mr = 439.94 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 25 reflections |
a = 12.296 (1) Å | θ = 10–13° |
b = 10.587 (2) Å | µ = 0.20 mm−1 |
c = 17.164 (2) Å | T = 293 K |
β = 99.77 (3)° | Block, colourless |
V = 2201.8 (6) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −14→0 |
ω/2θ scans | k = 0→12 |
4061 measured reflections | l = −20→20 |
3861 independent reflections | 3 standard reflections every 200 reflections |
2427 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.201 | w = 1/[σ2(Fo2) + (0.1259P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3861 reflections | Δρmax = 0.41 e Å−3 |
281 parameters | Δρmin = −0.30 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: 0.023 (4) |
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 | |
Cl | 0.70877 (8) | 0.22764 (10) | 1.15809 (5) | 0.0608 (4) | |
O1 | 0.4167 (2) | 0.2981 (3) | 0.99003 (15) | 0.0661 (8) | |
O2 | 0.2535 (2) | −0.1210 (2) | 0.48511 (14) | 0.0527 (7) | |
N1 | 0.5131 (3) | 0.3232 (4) | 1.04493 (17) | 0.0654 (10) | |
N2 | 0.5439 (2) | 0.3472 (3) | 0.92129 (16) | 0.0535 (8) | |
N3 | 0.3696 (2) | 0.1896 (3) | 0.80020 (15) | 0.0445 (7) | |
N4 | 0.3633 (2) | 0.0813 (3) | 0.64604 (15) | 0.0406 (7) | |
N5 | 0.2348 (2) | 0.0903 (2) | 0.49867 (14) | 0.0397 (7) | |
H5A | 0.2621 | 0.1559 | 0.5244 | 0.048* | |
C1 | 0.9115 (3) | 0.4799 (4) | 1.0904 (2) | 0.0627 (11) | |
H1B | 0.9810 | 0.5122 | 1.1103 | 0.075* | |
C2 | 0.8651 (3) | 0.3897 (4) | 1.1322 (2) | 0.0546 (10) | |
H2B | 0.9042 | 0.3587 | 1.1795 | 0.065* | |
C3 | 0.7597 (3) | 0.3448 (3) | 1.10373 (18) | 0.0447 (8) | |
C4 | 0.6990 (3) | 0.3899 (3) | 1.03310 (18) | 0.0429 (8) | |
C5 | 0.7497 (3) | 0.4767 (3) | 0.9908 (2) | 0.0528 (9) | |
H5B | 0.7125 | 0.5052 | 0.9422 | 0.063* | |
C6 | 0.8546 (3) | 0.5222 (4) | 1.0191 (2) | 0.0613 (10) | |
H6A | 0.8867 | 0.5813 | 0.9899 | 0.074* | |
C7 | 0.5849 (3) | 0.3516 (3) | 1.00099 (18) | 0.0419 (8) | |
C8 | 0.4427 (3) | 0.3149 (3) | 0.9191 (2) | 0.0479 (9) | |
C9 | 0.3508 (3) | 0.2962 (4) | 0.8509 (2) | 0.0602 (10) | |
H9A | 0.2826 | 0.2821 | 0.8709 | 0.072* | |
H9B | 0.3419 | 0.3727 | 0.8193 | 0.072* | |
C10 | 0.2646 (3) | 0.1553 (4) | 0.7496 (2) | 0.0527 (9) | |
H10A | 0.2355 | 0.2278 | 0.7182 | 0.063* | |
H10B | 0.2112 | 0.1306 | 0.7823 | 0.063* | |
C11 | 0.2826 (3) | 0.0478 (4) | 0.6957 (2) | 0.0528 (9) | |
H11A | 0.3083 | −0.0258 | 0.7272 | 0.063* | |
H11B | 0.2132 | 0.0262 | 0.6625 | 0.063* | |
C12 | 0.4677 (3) | 0.1107 (4) | 0.69733 (19) | 0.0508 (9) | |
H12A | 0.5229 | 0.1323 | 0.6654 | 0.061* | |
H12B | 0.4935 | 0.0374 | 0.7290 | 0.061* | |
C13 | 0.4519 (3) | 0.2200 (4) | 0.7507 (2) | 0.0518 (9) | |
H13A | 0.5216 | 0.2399 | 0.7841 | 0.062* | |
H13B | 0.4281 | 0.2938 | 0.7188 | 0.062* | |
C14 | 0.3749 (3) | −0.0180 (3) | 0.59039 (19) | 0.0523 (9) | |
H14A | 0.3786 | −0.0986 | 0.6176 | 0.063* | |
H14B | 0.4440 | −0.0063 | 0.5712 | 0.063* | |
C15 | 0.2808 (3) | −0.0222 (3) | 0.51981 (18) | 0.0401 (8) | |
C16 | 0.1426 (2) | 0.1083 (3) | 0.43565 (19) | 0.0367 (7) | |
C17 | 0.0442 (3) | 0.1530 (3) | 0.4556 (2) | 0.0430 (8) | |
C18 | −0.0437 (3) | 0.1719 (3) | 0.3946 (3) | 0.0570 (10) | |
H18A | −0.1101 | 0.2026 | 0.4061 | 0.068* | |
C19 | −0.0344 (3) | 0.1463 (4) | 0.3179 (3) | 0.0645 (12) | |
H19A | −0.0950 | 0.1577 | 0.2780 | 0.077* | |
C20 | 0.0645 (3) | 0.1035 (4) | 0.2991 (2) | 0.0589 (10) | |
H20A | 0.0702 | 0.0882 | 0.2466 | 0.071* | |
C21 | 0.1555 (3) | 0.0833 (3) | 0.35841 (19) | 0.0446 (8) | |
C22 | 0.0331 (3) | 0.1813 (4) | 0.5389 (2) | 0.0588 (10) | |
H22A | −0.0401 | 0.2117 | 0.5405 | 0.088* | |
H22B | 0.0859 | 0.2446 | 0.5598 | 0.088* | |
H22C | 0.0462 | 0.1058 | 0.5701 | 0.088* | |
C23 | 0.2630 (3) | 0.0395 (4) | 0.3375 (2) | 0.0572 (10) | |
H23A | 0.3165 | 0.0303 | 0.3849 | 0.086* | |
H23B | 0.2889 | 0.1005 | 0.3035 | 0.086* | |
H23C | 0.2525 | −0.0403 | 0.3108 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0680 (7) | 0.0673 (7) | 0.0437 (5) | −0.0099 (5) | 0.0002 (4) | 0.0126 (4) |
O1 | 0.0465 (15) | 0.099 (2) | 0.0523 (16) | −0.0037 (14) | 0.0055 (12) | 0.0066 (15) |
O2 | 0.0598 (16) | 0.0336 (13) | 0.0608 (15) | 0.0034 (11) | −0.0008 (12) | −0.0033 (11) |
N1 | 0.0505 (19) | 0.101 (3) | 0.0426 (17) | −0.0049 (18) | 0.0022 (15) | 0.0029 (17) |
N2 | 0.0495 (18) | 0.068 (2) | 0.0401 (16) | −0.0052 (15) | −0.0003 (13) | −0.0041 (14) |
N3 | 0.0323 (14) | 0.0564 (17) | 0.0431 (15) | −0.0039 (12) | 0.0014 (12) | −0.0039 (13) |
N4 | 0.0342 (14) | 0.0477 (16) | 0.0378 (14) | 0.0011 (12) | −0.0001 (11) | 0.0038 (12) |
N5 | 0.0401 (15) | 0.0295 (14) | 0.0461 (16) | 0.0001 (11) | −0.0020 (12) | −0.0073 (11) |
C1 | 0.057 (2) | 0.072 (3) | 0.060 (2) | −0.016 (2) | 0.0103 (19) | −0.014 (2) |
C2 | 0.053 (2) | 0.065 (3) | 0.0424 (19) | −0.0063 (19) | −0.0021 (17) | −0.0083 (18) |
C3 | 0.055 (2) | 0.0423 (19) | 0.0360 (17) | −0.0026 (16) | 0.0071 (15) | −0.0040 (14) |
C4 | 0.051 (2) | 0.0415 (19) | 0.0351 (17) | −0.0027 (15) | 0.0045 (14) | −0.0081 (14) |
C5 | 0.063 (2) | 0.047 (2) | 0.047 (2) | −0.0010 (18) | 0.0060 (17) | 0.0061 (17) |
C6 | 0.067 (3) | 0.054 (2) | 0.064 (2) | −0.015 (2) | 0.016 (2) | 0.0044 (19) |
C7 | 0.050 (2) | 0.0360 (18) | 0.0385 (17) | 0.0011 (15) | 0.0054 (15) | −0.0015 (14) |
C8 | 0.048 (2) | 0.045 (2) | 0.048 (2) | 0.0081 (16) | 0.0017 (16) | −0.0066 (16) |
C9 | 0.051 (2) | 0.072 (3) | 0.055 (2) | 0.0093 (19) | −0.0008 (18) | −0.0113 (19) |
C10 | 0.0328 (18) | 0.074 (3) | 0.049 (2) | −0.0025 (17) | 0.0009 (15) | 0.0021 (18) |
C11 | 0.047 (2) | 0.058 (2) | 0.051 (2) | −0.0112 (17) | 0.0033 (16) | 0.0072 (18) |
C12 | 0.0330 (18) | 0.072 (3) | 0.0454 (19) | 0.0006 (16) | −0.0001 (14) | 0.0045 (17) |
C13 | 0.0433 (19) | 0.064 (2) | 0.0455 (19) | −0.0141 (17) | 0.0012 (15) | −0.0005 (17) |
C14 | 0.054 (2) | 0.051 (2) | 0.0484 (19) | 0.0137 (17) | 0.0005 (16) | −0.0001 (17) |
C15 | 0.0426 (18) | 0.0340 (18) | 0.0437 (18) | 0.0032 (14) | 0.0078 (14) | 0.0034 (14) |
C16 | 0.0317 (16) | 0.0266 (16) | 0.0488 (18) | −0.0036 (12) | −0.0017 (14) | −0.0014 (13) |
C17 | 0.0373 (18) | 0.0282 (17) | 0.062 (2) | −0.0028 (14) | 0.0033 (15) | 0.0039 (15) |
C18 | 0.041 (2) | 0.044 (2) | 0.084 (3) | −0.0004 (16) | 0.0042 (19) | 0.014 (2) |
C19 | 0.044 (2) | 0.065 (3) | 0.075 (3) | −0.0110 (19) | −0.0151 (19) | 0.026 (2) |
C20 | 0.064 (3) | 0.061 (2) | 0.047 (2) | −0.016 (2) | −0.0042 (18) | 0.0029 (18) |
C21 | 0.047 (2) | 0.0395 (18) | 0.0441 (19) | −0.0067 (15) | −0.0006 (15) | −0.0015 (15) |
C22 | 0.051 (2) | 0.052 (2) | 0.079 (3) | −0.0033 (18) | 0.0239 (19) | −0.0107 (19) |
C23 | 0.058 (2) | 0.064 (2) | 0.050 (2) | −0.0029 (19) | 0.0104 (18) | −0.0089 (18) |
Geometric parameters (Å, º) top
Cl—C3 | 1.732 (3) | C10—C11 | 1.506 (5) |
O1—C8 | 1.321 (4) | C10—H10A | 0.9700 |
O1—N1 | 1.408 (4) | C10—H10B | 0.9700 |
O2—C15 | 1.221 (4) | C11—H11A | 0.9700 |
N1—C7 | 1.290 (4) | C11—H11B | 0.9700 |
N2—C8 | 1.285 (4) | C12—C13 | 1.508 (5) |
N2—C7 | 1.376 (4) | C12—H12A | 0.9700 |
N3—C13 | 1.464 (4) | C12—H12B | 0.9700 |
N3—C9 | 1.467 (4) | C13—H13A | 0.9700 |
N3—C10 | 1.474 (4) | C13—H13B | 0.9700 |
N4—C14 | 1.444 (4) | C14—C15 | 1.528 (4) |
N4—C11 | 1.458 (4) | C14—H14A | 0.9700 |
N4—C12 | 1.462 (4) | C14—H14B | 0.9700 |
N5—C15 | 1.342 (4) | C16—C21 | 1.387 (5) |
N5—C16 | 1.440 (4) | C16—C17 | 1.395 (4) |
N5—H5A | 0.8600 | C17—C18 | 1.384 (5) |
C1—C2 | 1.375 (5) | C17—C22 | 1.490 (5) |
C1—C6 | 1.378 (5) | C18—C19 | 1.368 (6) |
C1—H1B | 0.9300 | C18—H18A | 0.9300 |
C2—C3 | 1.389 (5) | C19—C20 | 1.386 (6) |
C2—H2B | 0.9300 | C19—H19A | 0.9300 |
C3—C4 | 1.395 (4) | C20—C21 | 1.395 (5) |
C4—C5 | 1.384 (5) | C20—H20A | 0.9300 |
C4—C7 | 1.475 (4) | C21—C23 | 1.501 (5) |
C5—C6 | 1.385 (5) | C22—H22A | 0.9600 |
C5—H5B | 0.9300 | C22—H22B | 0.9600 |
C6—H6A | 0.9300 | C22—H22C | 0.9600 |
C8—C9 | 1.496 (5) | C23—H23A | 0.9600 |
C9—H9A | 0.9700 | C23—H23B | 0.9600 |
C9—H9B | 0.9700 | C23—H23C | 0.9600 |
| | | |
C8—O1—N1 | 106.5 (3) | H11A—C11—H11B | 108.0 |
C7—N1—O1 | 103.5 (3) | N4—C12—C13 | 109.8 (3) |
C8—N2—C7 | 103.1 (3) | N4—C12—H12A | 109.7 |
C13—N3—C9 | 111.7 (3) | C13—C12—H12A | 109.7 |
C13—N3—C10 | 109.5 (3) | N4—C12—H12B | 109.7 |
C9—N3—C10 | 109.2 (3) | C13—C12—H12B | 109.7 |
C14—N4—C11 | 111.3 (3) | H12A—C12—H12B | 108.2 |
C14—N4—C12 | 112.2 (3) | N3—C13—C12 | 110.9 (3) |
C11—N4—C12 | 108.4 (2) | N3—C13—H13A | 109.5 |
C15—N5—C16 | 124.2 (3) | C12—C13—H13A | 109.5 |
C15—N5—H5A | 117.9 | N3—C13—H13B | 109.5 |
C16—N5—H5A | 117.9 | C12—C13—H13B | 109.5 |
C2—C1—C6 | 119.7 (4) | H13A—C13—H13B | 108.1 |
C2—C1—H1B | 120.1 | N4—C14—C15 | 113.5 (3) |
C6—C1—H1B | 120.1 | N4—C14—H14A | 108.9 |
C1—C2—C3 | 119.9 (3) | C15—C14—H14A | 108.9 |
C1—C2—H2B | 120.0 | N4—C14—H14B | 108.9 |
C3—C2—H2B | 120.0 | C15—C14—H14B | 108.9 |
C2—C3—C4 | 121.2 (3) | H14A—C14—H14B | 107.7 |
C2—C3—Cl | 117.1 (3) | O2—C15—N5 | 124.0 (3) |
C4—C3—Cl | 121.6 (3) | O2—C15—C14 | 121.3 (3) |
C5—C4—C3 | 117.5 (3) | N5—C15—C14 | 114.6 (3) |
C5—C4—C7 | 118.1 (3) | C21—C16—C17 | 122.9 (3) |
C3—C4—C7 | 124.4 (3) | C21—C16—N5 | 119.3 (3) |
C4—C5—C6 | 121.5 (3) | C17—C16—N5 | 117.8 (3) |
C4—C5—H5B | 119.3 | C18—C17—C16 | 117.5 (3) |
C6—C5—H5B | 119.3 | C18—C17—C22 | 120.6 (3) |
C1—C6—C5 | 120.1 (4) | C16—C17—C22 | 121.9 (3) |
C1—C6—H6A | 120.0 | C19—C18—C17 | 121.1 (4) |
C5—C6—H6A | 120.0 | C19—C18—H18A | 119.4 |
N1—C7—N2 | 113.7 (3) | C17—C18—H18A | 119.4 |
N1—C7—C4 | 123.2 (3) | C18—C19—C20 | 120.5 (3) |
N2—C7—C4 | 123.1 (3) | C18—C19—H19A | 119.7 |
N2—C8—O1 | 113.2 (3) | C20—C19—H19A | 119.7 |
N2—C8—C9 | 131.0 (3) | C19—C20—C21 | 120.5 (4) |
O1—C8—C9 | 115.8 (3) | C19—C20—H20A | 119.7 |
N3—C9—C8 | 113.1 (3) | C21—C20—H20A | 119.7 |
N3—C9—H9A | 109.0 | C16—C21—C20 | 117.4 (3) |
C8—C9—H9A | 109.0 | C16—C21—C23 | 122.4 (3) |
N3—C9—H9B | 109.0 | C20—C21—C23 | 120.2 (3) |
C8—C9—H9B | 109.0 | C17—C22—H22A | 109.5 |
H9A—C9—H9B | 107.8 | C17—C22—H22B | 109.5 |
N3—C10—C11 | 110.1 (3) | H22A—C22—H22B | 109.5 |
N3—C10—H10A | 109.6 | C17—C22—H22C | 109.5 |
C11—C10—H10A | 109.6 | H22A—C22—H22C | 109.5 |
N3—C10—H10B | 109.6 | H22B—C22—H22C | 109.5 |
C11—C10—H10B | 109.6 | C21—C23—H23A | 109.5 |
H10A—C10—H10B | 108.2 | C21—C23—H23B | 109.5 |
N4—C11—C10 | 111.1 (3) | H23A—C23—H23B | 109.5 |
N4—C11—H11A | 109.4 | C21—C23—H23C | 109.5 |
C10—C11—H11A | 109.4 | H23A—C23—H23C | 109.5 |
N4—C11—H11B | 109.4 | H23B—C23—H23C | 109.5 |
C10—C11—H11B | 109.4 | | |
| | | |
C8—O1—N1—C7 | −0.1 (4) | C14—N4—C11—C10 | −175.8 (3) |
C6—C1—C2—C3 | −2.2 (6) | C12—N4—C11—C10 | 60.3 (4) |
C1—C2—C3—C4 | −0.2 (5) | N3—C10—C11—N4 | −58.8 (4) |
C1—C2—C3—Cl | 177.9 (3) | C14—N4—C12—C13 | 176.6 (3) |
C2—C3—C4—C5 | 2.8 (5) | C11—N4—C12—C13 | −60.1 (4) |
Cl—C3—C4—C5 | −175.2 (3) | C9—N3—C13—C12 | −178.3 (3) |
C2—C3—C4—C7 | −176.9 (3) | C10—N3—C13—C12 | −57.3 (4) |
Cl—C3—C4—C7 | 5.0 (5) | N4—C12—C13—N3 | 59.9 (4) |
C3—C4—C5—C6 | −3.1 (5) | C11—N4—C14—C15 | 77.3 (3) |
C7—C4—C5—C6 | 176.7 (3) | C12—N4—C14—C15 | −161.0 (3) |
C2—C1—C6—C5 | 1.9 (6) | C16—N5—C15—O2 | 4.2 (5) |
C4—C5—C6—C1 | 0.8 (6) | C16—N5—C15—C14 | −177.8 (3) |
O1—N1—C7—N2 | 0.0 (4) | N4—C14—C15—O2 | −151.5 (3) |
O1—N1—C7—C4 | 177.7 (3) | N4—C14—C15—N5 | 30.5 (4) |
C8—N2—C7—N1 | 0.2 (4) | C15—N5—C16—C21 | −65.7 (4) |
C8—N2—C7—C4 | −177.5 (3) | C15—N5—C16—C17 | 115.6 (3) |
C5—C4—C7—N1 | −146.8 (4) | C21—C16—C17—C18 | 0.4 (5) |
C3—C4—C7—N1 | 33.0 (5) | N5—C16—C17—C18 | 179.0 (3) |
C5—C4—C7—N2 | 30.7 (5) | C21—C16—C17—C22 | −178.8 (3) |
C3—C4—C7—N2 | −149.5 (3) | N5—C16—C17—C22 | −0.2 (4) |
C7—N2—C8—O1 | −0.3 (4) | C16—C17—C18—C19 | 0.7 (5) |
C7—N2—C8—C9 | 178.3 (4) | C22—C17—C18—C19 | 180.0 (3) |
N1—O1—C8—N2 | 0.3 (4) | C17—C18—C19—C20 | −1.6 (6) |
N1—O1—C8—C9 | −178.5 (3) | C18—C19—C20—C21 | 1.4 (6) |
C13—N3—C9—C8 | −74.9 (4) | C17—C16—C21—C20 | −0.6 (5) |
C10—N3—C9—C8 | 163.9 (3) | N5—C16—C21—C20 | −179.2 (3) |
N2—C8—C9—N3 | 65.8 (5) | C17—C16—C21—C23 | 177.8 (3) |
O1—C8—C9—N3 | −115.7 (4) | N5—C16—C21—C23 | −0.7 (5) |
C13—N3—C10—C11 | 56.2 (4) | C19—C20—C21—C16 | −0.3 (5) |
C9—N3—C10—C11 | 178.8 (3) | C19—C20—C21—C23 | −178.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···N4 | 0.86 | 2.38 | 2.747 (4) | 106 |
N5—H5A···O2i | 0.86 | 2.37 | 3.070 (3) | 138 |
C13—H13A···N2 | 0.97 | 2.59 | 3.247 (5) | 125 |
C23—H23A···O2 | 0.96 | 2.56 | 3.068 (4) | 113 |
C23—H23A···N5 | 0.96 | 2.43 | 2.896 (4) | 110 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1. |