The molecular structure of the title compound, C
21H
19Cl
2N
3O
2, a potent glycogen phosphorylase a (GPa) inhibitor (IC
50 of 6.3 µ
M), consists of four distinct conjugated π systems separated by rotatable C—C bonds at the methylene groups. Molecules are linked into dimers disposed about a crystallographic centre of symmetry through a cyclic N—H
O hydrogen-bonding motif [graph set
R22(10)]. These dimers are further connected along the crystallographic
c axis by N—H
O hydrogen bonding between the amide groups [graph set
C(4)]. A comparison of this structure with that of the monohydrate of the significantly less active analogue (
S)-2-(3-benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-
N-(2-hydroxy-1-phenylethyl)acetamide (IC
50 of 120 µ
M) is presented.
Supporting information
CCDC reference: 967059
Cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001)
and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 2001) and
SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
2-(3-Benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-
N-(3,4-dichlorobenzyl)acetamide
top
Crystal data top
C21H19Cl2N3O2 | F(000) = 864 |
Mr = 416.29 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 1947 reflections |
a = 18.9215 (8) Å | θ = 3.5–28.9° |
b = 11.5507 (5) Å | µ = 0.36 mm−1 |
c = 8.9392 (3) Å | T = 200 K |
β = 93.874 (3)° | Plate, colourless |
V = 1949.26 (14) Å3 | 0.29 × 0.18 × 0.06 mm |
Z = 4 | |
Data collection top
Oxford GEMINI S Ultra diffractometer | 4456 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3126 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 16.0774 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω and φ scans | h = −24→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −13→15 |
Tmin = 0.904, Tmax = 0.979 | l = −11→10 |
8900 measured reflections | |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.3413P] where P = (Fo2 + 2Fc2)/3 |
4456 reflections | (Δ/σ)max < 0.001 |
261 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 | |
Cl17 | 0.01187 (4) | 0.39204 (8) | −0.18149 (7) | 0.0617 (3) | |
Cl18 | 0.04090 (3) | 0.12847 (7) | −0.10599 (7) | 0.0523 (2) | |
O2 | 0.47878 (7) | 0.38715 (12) | 0.36430 (15) | 0.0292 (4) | |
O12 | 0.36288 (7) | 0.17730 (13) | 0.43693 (14) | 0.0299 (5) | |
N1 | 0.49932 (8) | 0.19497 (14) | 0.33929 (17) | 0.0223 (5) | |
N3 | 0.60227 (10) | 0.41821 (17) | 0.5336 (2) | 0.0341 (6) | |
N11 | 0.31490 (9) | 0.24570 (17) | 0.2172 (2) | 0.0284 (6) | |
C2 | 0.51697 (10) | 0.30181 (18) | 0.3965 (2) | 0.0223 (6) | |
C3 | 0.58202 (10) | 0.30810 (18) | 0.4918 (2) | 0.0234 (6) | |
C4 | 0.61913 (11) | 0.20999 (19) | 0.5276 (2) | 0.0298 (6) | |
C5 | 0.59536 (11) | 0.10202 (19) | 0.4706 (2) | 0.0317 (7) | |
C6 | 0.53699 (11) | 0.09613 (18) | 0.3768 (2) | 0.0284 (6) | |
C11 | 0.43813 (10) | 0.19012 (19) | 0.2318 (2) | 0.0269 (6) | |
C12 | 0.36871 (10) | 0.20587 (18) | 0.3054 (2) | 0.0234 (6) | |
C13 | 0.24491 (11) | 0.2561 (2) | 0.2742 (2) | 0.0334 (7) | |
C14 | 0.18896 (10) | 0.2890 (2) | 0.1548 (2) | 0.0279 (6) | |
C15 | 0.17688 (13) | 0.4037 (2) | 0.1177 (3) | 0.0368 (7) | |
C16 | 0.12307 (13) | 0.4348 (2) | 0.0138 (3) | 0.0397 (8) | |
C17 | 0.08051 (11) | 0.3512 (2) | −0.0545 (2) | 0.0355 (8) | |
C18 | 0.09268 (10) | 0.2355 (2) | −0.0206 (2) | 0.0314 (7) | |
C19 | 0.14641 (10) | 0.20476 (19) | 0.0839 (2) | 0.0281 (6) | |
C31 | 0.66989 (12) | 0.4393 (2) | 0.6130 (3) | 0.0369 (7) | |
C32 | 0.73130 (11) | 0.41581 (19) | 0.5170 (3) | 0.0321 (7) | |
C33 | 0.72526 (12) | 0.4363 (2) | 0.3636 (3) | 0.0392 (8) | |
C34 | 0.78102 (14) | 0.4140 (2) | 0.2756 (3) | 0.0467 (9) | |
C35 | 0.84427 (13) | 0.3723 (2) | 0.3401 (3) | 0.0499 (9) | |
C36 | 0.85115 (13) | 0.3511 (2) | 0.4922 (3) | 0.0501 (9) | |
C37 | 0.79493 (12) | 0.3720 (2) | 0.5794 (3) | 0.0395 (8) | |
H3 | 0.5730 (13) | 0.466 (2) | 0.540 (3) | 0.040 (7)* | |
H4 | 0.66130 | 0.21420 | 0.59140 | 0.0360* | |
H5 | 0.62070 | 0.03340 | 0.49840 | 0.0380* | |
H6 | 0.52170 | 0.02360 | 0.33630 | 0.0340* | |
H11 | 0.3211 (12) | 0.262 (2) | 0.138 (3) | 0.029 (7)* | |
H11A | 0.43750 | 0.11690 | 0.18320 | 0.0320* | |
H11B | 0.44230 | 0.24970 | 0.15970 | 0.0320* | |
H13A | 0.23250 | 0.18380 | 0.31600 | 0.0400* | |
H13B | 0.24670 | 0.31380 | 0.35030 | 0.0400* | |
H15 | 0.20610 | 0.46190 | 0.16450 | 0.0440* | |
H16 | 0.11550 | 0.51410 | −0.01070 | 0.0480* | |
H19 | 0.15440 | 0.12540 | 0.10740 | 0.0340* | |
H31A | 0.67430 | 0.39040 | 0.69870 | 0.0440* | |
H31B | 0.67190 | 0.51800 | 0.64410 | 0.0440* | |
H33 | 0.68220 | 0.46630 | 0.31850 | 0.0470* | |
H34 | 0.77580 | 0.42740 | 0.17060 | 0.0560* | |
H35 | 0.88290 | 0.35800 | 0.28010 | 0.0600* | |
H36 | 0.89460 | 0.32250 | 0.53710 | 0.0600* | |
H37 | 0.79990 | 0.35590 | 0.68380 | 0.0470* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl17 | 0.0435 (4) | 0.0931 (6) | 0.0472 (4) | 0.0309 (4) | −0.0053 (3) | 0.0138 (4) |
Cl18 | 0.0337 (3) | 0.0666 (5) | 0.0553 (4) | −0.0130 (3) | −0.0075 (3) | −0.0132 (4) |
O2 | 0.0312 (8) | 0.0235 (8) | 0.0326 (7) | 0.0081 (6) | 0.0002 (6) | −0.0003 (6) |
O12 | 0.0303 (8) | 0.0386 (9) | 0.0212 (7) | 0.0026 (7) | 0.0038 (5) | 0.0015 (7) |
N1 | 0.0217 (8) | 0.0216 (9) | 0.0238 (8) | −0.0001 (7) | 0.0034 (6) | −0.0033 (7) |
N3 | 0.0215 (10) | 0.0257 (10) | 0.0546 (12) | 0.0021 (8) | −0.0002 (8) | −0.0136 (9) |
N11 | 0.0233 (9) | 0.0429 (12) | 0.0191 (9) | −0.0034 (8) | 0.0026 (7) | 0.0025 (9) |
C2 | 0.0244 (10) | 0.0218 (10) | 0.0212 (9) | 0.0013 (8) | 0.0048 (7) | 0.0018 (8) |
C3 | 0.0219 (10) | 0.0227 (11) | 0.0261 (10) | −0.0001 (8) | 0.0045 (8) | −0.0015 (9) |
C4 | 0.0228 (10) | 0.0301 (12) | 0.0361 (11) | 0.0027 (9) | −0.0015 (8) | 0.0026 (10) |
C5 | 0.0319 (12) | 0.0203 (11) | 0.0430 (12) | 0.0073 (9) | 0.0035 (9) | 0.0069 (10) |
C6 | 0.0325 (12) | 0.0169 (10) | 0.0366 (11) | −0.0001 (9) | 0.0089 (9) | −0.0029 (9) |
C11 | 0.0263 (11) | 0.0320 (12) | 0.0224 (10) | −0.0016 (9) | 0.0009 (8) | −0.0060 (9) |
C12 | 0.0255 (10) | 0.0224 (11) | 0.0223 (9) | −0.0033 (8) | 0.0014 (7) | −0.0067 (9) |
C13 | 0.0253 (11) | 0.0504 (15) | 0.0245 (10) | −0.0044 (10) | 0.0025 (8) | 0.0023 (11) |
C14 | 0.0216 (10) | 0.0387 (13) | 0.0237 (10) | −0.0002 (9) | 0.0047 (8) | −0.0003 (10) |
C15 | 0.0405 (13) | 0.0345 (13) | 0.0358 (12) | −0.0049 (11) | 0.0052 (10) | −0.0055 (11) |
C16 | 0.0454 (14) | 0.0321 (13) | 0.0427 (13) | 0.0120 (11) | 0.0104 (11) | 0.0038 (11) |
C17 | 0.0269 (12) | 0.0524 (16) | 0.0276 (11) | 0.0119 (11) | 0.0044 (8) | 0.0059 (11) |
C18 | 0.0222 (10) | 0.0428 (14) | 0.0292 (10) | −0.0015 (10) | 0.0026 (8) | −0.0030 (10) |
C19 | 0.0231 (10) | 0.0308 (12) | 0.0307 (10) | 0.0002 (9) | 0.0031 (8) | 0.0012 (10) |
C31 | 0.0278 (12) | 0.0368 (13) | 0.0457 (13) | −0.0043 (10) | −0.0010 (9) | −0.0134 (11) |
C32 | 0.0246 (11) | 0.0261 (12) | 0.0454 (13) | −0.0056 (9) | 0.0003 (9) | −0.0099 (10) |
C33 | 0.0309 (12) | 0.0371 (14) | 0.0491 (14) | −0.0056 (10) | −0.0017 (10) | −0.0008 (12) |
C34 | 0.0428 (15) | 0.0522 (17) | 0.0456 (14) | −0.0134 (12) | 0.0076 (11) | −0.0044 (13) |
C35 | 0.0336 (14) | 0.0531 (17) | 0.0645 (17) | −0.0069 (12) | 0.0153 (12) | −0.0158 (15) |
C36 | 0.0280 (13) | 0.0509 (17) | 0.0708 (18) | 0.0051 (12) | −0.0019 (12) | −0.0109 (15) |
C37 | 0.0332 (13) | 0.0378 (14) | 0.0469 (13) | −0.0016 (10) | −0.0021 (10) | −0.0061 (12) |
Geometric parameters (Å, º) top
Cl17—C17 | 1.732 (2) | C31—C32 | 1.515 (3) |
Cl18—C18 | 1.723 (2) | C32—C37 | 1.388 (3) |
O2—C2 | 1.244 (2) | C32—C33 | 1.389 (4) |
O12—C12 | 1.233 (2) | C33—C34 | 1.382 (4) |
N1—C2 | 1.369 (3) | C34—C35 | 1.380 (4) |
N1—C6 | 1.375 (3) | C35—C36 | 1.379 (4) |
N1—C11 | 1.455 (2) | C36—C37 | 1.382 (3) |
N3—C3 | 1.373 (3) | C4—H4 | 0.9500 |
N3—C31 | 1.441 (3) | C5—H5 | 0.9500 |
N11—C12 | 1.327 (3) | C6—H6 | 0.9500 |
N11—C13 | 1.456 (3) | C11—H11A | 0.9500 |
N3—H3 | 0.79 (2) | C11—H11B | 0.9500 |
N11—H11 | 0.75 (3) | C13—H13A | 0.9500 |
C2—C3 | 1.451 (3) | C13—H13B | 0.9500 |
C3—C4 | 1.360 (3) | C15—H15 | 0.9500 |
C4—C5 | 1.409 (3) | C16—H16 | 0.9500 |
C5—C6 | 1.343 (3) | C19—H19 | 0.9500 |
C11—C12 | 1.519 (3) | C31—H31A | 0.9500 |
C13—C14 | 1.501 (3) | C31—H31B | 0.9500 |
C14—C19 | 1.388 (3) | C33—H33 | 0.9500 |
C14—C15 | 1.381 (3) | C34—H34 | 0.9500 |
C15—C16 | 1.379 (4) | C35—H35 | 0.9500 |
C16—C17 | 1.374 (3) | C36—H36 | 0.9500 |
C17—C18 | 1.386 (3) | C37—H37 | 0.9500 |
C18—C19 | 1.380 (3) | | |
| | | |
Cl17···Cl18 | 3.1584 (12) | C32···C4 | 3.193 (3) |
Cl17···Cl18i | 3.4362 (11) | C33···C3 | 3.357 (3) |
Cl17···C16ii | 3.645 (3) | C2···H11Bix | 2.8900 |
Cl17···C19iii | 3.585 (2) | C4···H31A | 2.7500 |
Cl18···Cl17 | 3.1584 (12) | C5···H31Aiii | 2.9400 |
Cl18···Cl17iv | 3.4362 (11) | C16···H34xi | 3.0600 |
Cl18···H35v | 3.1000 | C19···H13Biii | 2.9200 |
O2···N3 | 2.721 (2) | C31···H4 | 2.6100 |
O2···C12 | 2.975 (2) | C32···H4 | 2.7800 |
O2···N3vi | 2.903 (2) | C34···H19vii | 2.8900 |
O2···C6vii | 3.236 (2) | C34···H4iii | 3.0900 |
O12···C2 | 3.293 (2) | C35···H19vii | 2.9600 |
O12···C5viii | 3.410 (3) | C35···H37iii | 3.0700 |
O12···C11ix | 3.288 (2) | C37···H15vi | 2.9900 |
O12···N11ix | 2.864 (2) | H3···O2 | 2.47 (3) |
O12···N1 | 2.788 (2) | H3···O2vi | 2.16 (2) |
O2···H11B | 2.4800 | H4···C31 | 2.6100 |
O2···H3vi | 2.16 (2) | H4···C32 | 2.7800 |
O2···H3 | 2.47 (3) | H4···H31A | 2.2600 |
O2···H6vii | 2.3900 | H4···C34ix | 3.0900 |
O12···H13A | 2.6300 | H5···O12viii | 2.5200 |
O12···H5viii | 2.5200 | H6···H11A | 2.3000 |
O12···H13B | 2.7700 | H6···O2x | 2.3900 |
O12···H11ix | 2.13 (3) | H11···H11B | 2.2900 |
O12···H11Bix | 2.5600 | H11···O12iii | 2.13 (3) |
N1···O12 | 2.788 (2) | H11A···H6 | 2.3000 |
N3···O2 | 2.721 (2) | H11B···O2 | 2.4800 |
N3···O2vi | 2.903 (2) | H11B···H11 | 2.2900 |
N3···C6ix | 3.388 (3) | H11B···O12iii | 2.5600 |
N11···O12iii | 2.864 (2) | H11B···C2iii | 2.8900 |
N3···H33 | 2.5900 | H13A···O12 | 2.6300 |
C2···O12 | 3.293 (2) | H13A···H19 | 2.4000 |
C2···C11ix | 3.438 (3) | H13B···O12 | 2.7700 |
C3···C33 | 3.357 (3) | H13B···H15 | 2.4700 |
C3···C11ix | 3.578 (3) | H13B···H31Bvi | 2.4800 |
C4···C32 | 3.193 (3) | H13B···C19ix | 2.9200 |
C5···O12viii | 3.410 (3) | H15···H13B | 2.4700 |
C6···O2x | 3.236 (2) | H15···C37vi | 2.9900 |
C6···C31iii | 3.585 (3) | H15···H37vi | 2.5100 |
C6···N3iii | 3.388 (3) | H19···H13A | 2.4000 |
C6···C6viii | 3.487 (3) | H19···C34x | 2.8900 |
C11···O12iii | 3.288 (2) | H19···C35x | 2.9600 |
C11···C3iii | 3.578 (3) | H31A···C4 | 2.7500 |
C11···C2iii | 3.438 (3) | H31A···H4 | 2.2600 |
C12···O2 | 2.975 (2) | H31A···H37 | 2.4200 |
C13···C18ix | 3.519 (3) | H31A···C5ix | 2.9400 |
C13···C19ix | 3.470 (3) | H31B···H13Bvi | 2.4800 |
C14···C18ix | 3.540 (3) | H33···N3 | 2.5900 |
C16···Cl17ii | 3.645 (3) | H34···C16xi | 3.0600 |
C18···C14iii | 3.540 (3) | H35···Cl18xii | 3.1000 |
C18···C13iii | 3.519 (3) | H37···H31A | 2.4200 |
C19···Cl17ix | 3.585 (2) | H37···H15vi | 2.5100 |
C19···C13iii | 3.470 (3) | H37···C35ix | 3.0700 |
C31···C6ix | 3.585 (3) | | |
| | | |
C2—N1—C6 | 123.23 (16) | C34—C35—C36 | 119.7 (2) |
C2—N1—C11 | 116.41 (16) | C35—C36—C37 | 120.0 (2) |
C6—N1—C11 | 120.35 (16) | C32—C37—C36 | 121.1 (2) |
C3—N3—C31 | 120.85 (18) | C3—C4—H4 | 120.00 |
C12—N11—C13 | 120.01 (17) | C5—C4—H4 | 120.00 |
C3—N3—H3 | 119.0 (18) | C4—C5—H5 | 120.00 |
C31—N3—H3 | 116.8 (18) | C6—C5—H5 | 120.00 |
C13—N11—H11 | 120.9 (18) | N1—C6—H6 | 120.00 |
C12—N11—H11 | 119.1 (17) | C5—C6—H6 | 120.00 |
O2—C2—C3 | 123.54 (18) | N1—C11—H11A | 109.00 |
N1—C2—C3 | 116.14 (17) | N1—C11—H11B | 109.00 |
O2—C2—N1 | 120.31 (17) | C12—C11—H11A | 109.00 |
N3—C3—C2 | 114.61 (18) | C12—C11—H11B | 109.00 |
C2—C3—C4 | 120.04 (19) | H11A—C11—H11B | 109.00 |
N3—C3—C4 | 125.30 (18) | N11—C13—H13A | 109.00 |
C3—C4—C5 | 120.35 (18) | N11—C13—H13B | 109.00 |
C4—C5—C6 | 120.0 (2) | C14—C13—H13A | 109.00 |
N1—C6—C5 | 120.08 (19) | C14—C13—H13B | 109.00 |
N1—C11—C12 | 112.47 (15) | H13A—C13—H13B | 109.00 |
O12—C12—C11 | 121.10 (17) | C14—C15—H15 | 119.00 |
N11—C12—C11 | 115.80 (16) | C16—C15—H15 | 120.00 |
O12—C12—N11 | 123.00 (18) | C15—C16—H16 | 120.00 |
N11—C13—C14 | 112.75 (15) | C17—C16—H16 | 120.00 |
C13—C14—C15 | 120.7 (2) | C14—C19—H19 | 120.00 |
C13—C14—C19 | 120.4 (2) | C18—C19—H19 | 120.00 |
C15—C14—C19 | 118.77 (19) | N3—C31—H31A | 109.00 |
C14—C15—C16 | 121.0 (2) | N3—C31—H31B | 109.00 |
C15—C16—C17 | 120.0 (2) | C32—C31—H31A | 109.00 |
Cl17—C17—C16 | 119.41 (18) | C32—C31—H31B | 109.00 |
Cl17—C17—C18 | 120.80 (16) | H31A—C31—H31B | 109.00 |
C16—C17—C18 | 119.79 (19) | C32—C33—H33 | 119.00 |
C17—C18—C19 | 120.00 (19) | C34—C33—H33 | 119.00 |
Cl18—C18—C17 | 120.91 (15) | C33—C34—H34 | 120.00 |
Cl18—C18—C19 | 119.08 (17) | C35—C34—H34 | 120.00 |
C14—C19—C18 | 120.4 (2) | C34—C35—H35 | 120.00 |
N3—C31—C32 | 112.3 (2) | C36—C35—H35 | 120.00 |
C31—C32—C33 | 120.9 (2) | C35—C36—H36 | 120.00 |
C31—C32—C37 | 121.0 (2) | C37—C36—H36 | 120.00 |
C33—C32—C37 | 118.1 (2) | C32—C37—H37 | 119.00 |
C32—C33—C34 | 121.0 (2) | C36—C37—H37 | 119.00 |
C33—C34—C35 | 120.1 (2) | | |
| | | |
C6—N1—C2—O2 | −176.31 (17) | N11—C13—C14—C19 | 97.2 (2) |
C6—N1—C2—C3 | 4.8 (3) | C13—C14—C15—C16 | −176.5 (2) |
C11—N1—C2—O2 | 4.9 (3) | C19—C14—C15—C16 | 0.9 (3) |
C11—N1—C2—C3 | −174.02 (16) | C13—C14—C19—C18 | 176.80 (17) |
C2—N1—C6—C5 | −1.9 (3) | C15—C14—C19—C18 | −0.6 (3) |
C11—N1—C6—C5 | 176.85 (17) | C14—C15—C16—C17 | 0.0 (4) |
C2—N1—C11—C12 | −72.9 (2) | C15—C16—C17—Cl17 | 178.50 (19) |
C6—N1—C11—C12 | 108.3 (2) | C15—C16—C17—C18 | −1.2 (3) |
C31—N3—C3—C2 | −172.51 (19) | C16—C17—C18—C19 | 1.4 (3) |
C31—N3—C3—C4 | 4.7 (3) | Cl17—C17—C18—Cl18 | 1.1 (2) |
C3—N3—C31—C32 | 67.5 (3) | Cl17—C17—C18—C19 | −178.24 (15) |
C13—N11—C12—O12 | −0.7 (3) | C16—C17—C18—Cl18 | −179.23 (17) |
C13—N11—C12—C11 | 175.69 (18) | Cl18—C18—C19—C14 | −179.90 (14) |
C12—N11—C13—C14 | −173.21 (19) | C17—C18—C19—C14 | −0.5 (3) |
N1—C2—C3—N3 | 173.08 (16) | N3—C31—C32—C37 | −146.1 (2) |
N1—C2—C3—C4 | −4.3 (3) | N3—C31—C32—C33 | 33.2 (3) |
O2—C2—C3—N3 | −5.8 (3) | C31—C32—C33—C34 | −179.4 (2) |
O2—C2—C3—C4 | 176.87 (18) | C31—C32—C37—C36 | −179.6 (2) |
N3—C3—C4—C5 | −176.03 (18) | C33—C32—C37—C36 | 1.1 (3) |
C2—C3—C4—C5 | 1.0 (3) | C37—C32—C33—C34 | −0.2 (3) |
C3—C4—C5—C6 | 2.0 (3) | C32—C33—C34—C35 | −0.9 (4) |
C4—C5—C6—N1 | −1.7 (3) | C33—C34—C35—C36 | 1.1 (4) |
N1—C11—C12—N11 | 155.49 (18) | C34—C35—C36—C37 | −0.2 (4) |
N1—C11—C12—O12 | −28.1 (3) | C35—C36—C37—C32 | −0.9 (4) |
N11—C13—C14—C15 | −85.5 (2) | | |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z−1/2; (iv) −x, y−1/2, −z−1/2; (v) x−1, −y+1/2, z−1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+1, −y, −z+1; (ix) x, −y+1/2, z+1/2; (x) −x+1, y−1/2, −z+1/2; (xi) −x+1, −y+1, −z; (xii) x+1, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.79 (2) | 2.47 (3) | 2.721 (2) | 100 (2) |
N3—H3···O2vi | 0.79 (2) | 2.16 (2) | 2.903 (2) | 157 (2) |
N11—H11···O12iii | 0.75 (3) | 2.13 (3) | 2.864 (2) | 166 (2) |
Symmetry codes: (iii) x, −y+1/2, z−1/2; (vi) −x+1, −y+1, −z+1. |