Download citation
Download citation
link to html
The title compound, C18H19N3O·0.5H2O, was synthesized by the reaction of benz­aldehyde with malono­nitrile, dimedone and ammonium acetate under microwave irradiation. X-ray analysis reveals that in both crystallographically independent molecules in the asymmetric unit, the di­hydro­pyridine rings adopt distorted boat conformations and the cyclo­hexene rings adopt envelope conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007403/ci6534sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007403/ci6534Isup2.hkl
Contains datablock I

CCDC reference: 270265

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.068
  • wR factor = 0.143
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C16 .. 6.01 su PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis(2-amino-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline- 3-carbonitrile) monohydrate top
Crystal data top
C18H19N3O·0.5H2OF(000) = 1288
Mr = 302.37Dx = 1.265 Mg m3
Monoclinic, P21/cMelting point = 553–554 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71070 Å
a = 9.1652 (13) ÅCell parameters from 12424 reflections
b = 14.716 (2) Åθ = 3.1–27.5°
c = 23.596 (3) ŵ = 0.08 mm1
β = 93.918 (4)°T = 193 K
V = 3175.1 (7) Å3Block, yellow
Z = 80.48 × 0.39 × 0.20 mm
Data collection top
Rigaku Mercury
diffractometer
7266 independent reflections
Radiation source: fine-focus sealed tube5982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1111
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1919
Tmin = 0.962, Tmax = 0.984l = 2530
35240 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0465P)2 + 1.3409P]
where P = (Fo2 + 2Fc2)/3
7266 reflections(Δ/σ)max = 0.001
419 parametersΔρmax = 0.22 e Å3
3 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
O10.61224 (14)0.70192 (9)0.36733 (6)0.0367 (3)
O20.54389 (17)0.74046 (10)0.02206 (7)0.0442 (4)
O30.8023 (2)0.84786 (13)0.37303 (11)0.0753 (7)
N10.44188 (16)0.41692 (10)0.42385 (7)0.0301 (4)
H10.45770.35790.42490.036*
N20.05650 (19)0.60365 (12)0.48291 (8)0.0402 (4)
N30.24352 (18)0.38914 (12)0.47481 (8)0.0388 (4)
H3A0.16310.40510.49060.047*
H3B0.27520.33280.47770.047*
N40.42462 (18)0.45853 (11)0.10099 (7)0.0325 (4)
H40.35400.42040.10780.039*
N50.9350 (2)0.45265 (14)0.14893 (10)0.0517 (5)
N60.58308 (19)0.35743 (11)0.14713 (8)0.0389 (4)
H6A0.67000.34060.16160.047*
H6B0.50780.32070.14890.047*
C10.54090 (19)0.47211 (13)0.40004 (8)0.0267 (4)
C20.51236 (19)0.56114 (12)0.39010 (8)0.0250 (4)
C30.36426 (19)0.60218 (12)0.39954 (8)0.0243 (4)
H30.38100.66160.41950.029*
C40.28265 (19)0.54014 (12)0.43826 (8)0.0260 (4)
C50.3179 (2)0.45087 (13)0.44632 (8)0.0275 (4)
C60.6282 (2)0.61878 (13)0.37241 (8)0.0276 (4)
C70.7745 (2)0.57653 (14)0.36273 (9)0.0356 (5)
H7A0.83810.58150.39820.043*
H7B0.82090.61190.33310.043*
C80.7678 (2)0.47702 (14)0.34463 (9)0.0316 (4)
C90.6804 (2)0.42522 (13)0.38719 (9)0.0325 (4)
H9A0.65680.36400.37180.039*
H9B0.74200.41740.42300.039*
C100.27117 (19)0.62009 (12)0.34445 (8)0.0260 (4)
C110.2753 (2)0.56255 (14)0.29774 (9)0.0337 (4)
H110.34170.51290.29910.040*
C120.1840 (2)0.57676 (17)0.24941 (9)0.0434 (5)
H120.18770.53680.21790.052*
C130.0875 (2)0.64900 (18)0.24688 (10)0.0478 (6)
H130.02510.65890.21360.057*
C140.0819 (2)0.70656 (16)0.29262 (10)0.0432 (5)
H140.01590.75640.29090.052*
C150.1721 (2)0.69209 (14)0.34114 (9)0.0338 (5)
H150.16650.73180.37270.041*
C160.1574 (2)0.57422 (12)0.46267 (8)0.0285 (4)
C170.6966 (3)0.46818 (17)0.28460 (9)0.0451 (6)
H17A0.68780.40380.27440.068*
H17B0.75710.49920.25790.068*
H17C0.59920.49590.28290.068*
C180.9229 (2)0.43758 (16)0.34611 (11)0.0460 (6)
H18A0.96830.44150.38490.069*
H18B0.98120.47220.32030.069*
H18C0.91820.37380.33410.069*
C190.3921 (2)0.53490 (12)0.06973 (8)0.0288 (4)
C200.4937 (2)0.60064 (12)0.06356 (8)0.0285 (4)
C210.6424 (2)0.59858 (13)0.09601 (8)0.0305 (4)
H210.71820.61600.06950.037*
C220.6738 (2)0.50224 (13)0.11683 (9)0.0314 (4)
C230.5652 (2)0.43973 (13)0.12210 (8)0.0307 (4)
C240.4544 (2)0.67970 (13)0.02927 (8)0.0309 (4)
C250.3012 (2)0.68769 (14)0.00288 (9)0.0350 (5)
H25A0.29920.66400.03640.042*
H25B0.27470.75290.00060.042*
C260.1849 (2)0.63754 (13)0.03446 (8)0.0324 (4)
C270.2389 (2)0.53988 (13)0.04367 (9)0.0336 (5)
H27A0.17310.50800.06860.040*
H27B0.23390.50790.00670.040*
C280.6464 (2)0.66727 (12)0.14447 (8)0.0286 (4)
C290.7492 (2)0.73700 (14)0.14874 (9)0.0348 (5)
H290.82100.74110.12170.042*
C300.7479 (2)0.80067 (15)0.19212 (10)0.0423 (5)
H300.81890.84780.19470.051*
C310.6443 (2)0.79573 (15)0.23133 (9)0.0418 (5)
H310.64270.83990.26060.050*
C320.5420 (2)0.72642 (15)0.22819 (9)0.0406 (5)
H320.47070.72260.25550.049*
C330.5440 (2)0.66309 (14)0.18530 (9)0.0356 (5)
H330.47390.61550.18350.043*
C340.8180 (2)0.47669 (14)0.13506 (9)0.0357 (5)
C350.1639 (2)0.68351 (15)0.09140 (9)0.0399 (5)
H35A0.25770.68570.11390.060*
H35B0.09320.64890.11200.060*
H35C0.12750.74550.08480.060*
C360.0389 (2)0.63815 (16)0.00084 (10)0.0445 (5)
H36A0.00800.70110.00810.067*
H36B0.03490.60670.02000.067*
H36C0.05010.60710.03700.067*
H3C0.775 (3)0.7944 (10)0.3644 (13)0.084 (10)*
H3D0.886 (2)0.860 (2)0.3623 (16)0.118 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0318 (7)0.0271 (7)0.0518 (9)0.0030 (6)0.0067 (7)0.0024 (6)
O20.0489 (9)0.0316 (8)0.0526 (10)0.0138 (7)0.0066 (8)0.0070 (7)
O30.0369 (10)0.0495 (12)0.142 (2)0.0079 (9)0.0225 (12)0.0437 (12)
N10.0272 (8)0.0204 (8)0.0442 (10)0.0040 (6)0.0136 (7)0.0038 (7)
N20.0359 (10)0.0344 (10)0.0523 (11)0.0027 (8)0.0172 (9)0.0013 (8)
N30.0343 (9)0.0297 (9)0.0547 (11)0.0051 (7)0.0203 (8)0.0110 (8)
N40.0279 (8)0.0254 (8)0.0445 (10)0.0048 (7)0.0059 (7)0.0048 (7)
N50.0354 (11)0.0531 (12)0.0670 (14)0.0058 (9)0.0052 (10)0.0067 (10)
N60.0334 (9)0.0283 (9)0.0550 (11)0.0002 (7)0.0035 (8)0.0085 (8)
C10.0226 (9)0.0294 (10)0.0285 (9)0.0007 (7)0.0044 (8)0.0002 (8)
C20.0229 (9)0.0259 (9)0.0262 (9)0.0011 (7)0.0027 (7)0.0013 (7)
C30.0229 (9)0.0216 (9)0.0285 (9)0.0001 (7)0.0035 (7)0.0003 (7)
C40.0227 (9)0.0269 (9)0.0287 (9)0.0020 (7)0.0050 (7)0.0001 (7)
C50.0229 (9)0.0304 (10)0.0298 (10)0.0001 (8)0.0055 (8)0.0006 (8)
C60.0280 (10)0.0286 (10)0.0261 (9)0.0021 (8)0.0003 (8)0.0009 (8)
C70.0252 (10)0.0357 (11)0.0463 (12)0.0031 (9)0.0061 (9)0.0026 (9)
C80.0251 (9)0.0335 (10)0.0373 (11)0.0034 (8)0.0089 (8)0.0014 (9)
C90.0278 (10)0.0314 (10)0.0391 (11)0.0062 (8)0.0087 (9)0.0051 (9)
C100.0229 (9)0.0247 (9)0.0308 (10)0.0028 (7)0.0055 (8)0.0034 (7)
C110.0295 (10)0.0360 (11)0.0355 (11)0.0010 (9)0.0023 (8)0.0022 (9)
C120.0403 (12)0.0575 (15)0.0322 (11)0.0030 (11)0.0009 (9)0.0031 (10)
C130.0356 (12)0.0711 (17)0.0358 (12)0.0048 (12)0.0050 (10)0.0115 (11)
C140.0359 (11)0.0490 (13)0.0446 (13)0.0107 (10)0.0021 (10)0.0142 (11)
C150.0310 (10)0.0311 (10)0.0399 (11)0.0024 (8)0.0056 (9)0.0044 (9)
C160.0296 (10)0.0240 (9)0.0321 (10)0.0011 (8)0.0043 (8)0.0003 (8)
C170.0458 (13)0.0524 (14)0.0381 (12)0.0031 (11)0.0113 (10)0.0041 (10)
C180.0300 (11)0.0459 (13)0.0640 (16)0.0066 (10)0.0182 (11)0.0070 (11)
C190.0338 (10)0.0234 (9)0.0298 (10)0.0020 (8)0.0060 (8)0.0029 (8)
C200.0312 (10)0.0252 (9)0.0300 (10)0.0026 (8)0.0081 (8)0.0030 (8)
C210.0292 (10)0.0264 (10)0.0373 (11)0.0049 (8)0.0112 (8)0.0032 (8)
C220.0287 (10)0.0282 (10)0.0380 (11)0.0004 (8)0.0083 (8)0.0038 (8)
C230.0326 (10)0.0249 (9)0.0354 (11)0.0026 (8)0.0082 (8)0.0007 (8)
C240.0404 (11)0.0248 (9)0.0284 (10)0.0056 (8)0.0088 (9)0.0026 (8)
C250.0453 (12)0.0293 (10)0.0306 (10)0.0027 (9)0.0036 (9)0.0025 (8)
C260.0382 (11)0.0283 (10)0.0303 (10)0.0027 (9)0.0002 (9)0.0019 (8)
C270.0354 (11)0.0283 (10)0.0368 (11)0.0058 (8)0.0007 (9)0.0020 (8)
C280.0264 (9)0.0238 (9)0.0355 (10)0.0003 (7)0.0009 (8)0.0001 (8)
C290.0273 (10)0.0308 (10)0.0466 (12)0.0037 (8)0.0039 (9)0.0002 (9)
C300.0395 (12)0.0320 (11)0.0547 (14)0.0093 (10)0.0027 (11)0.0054 (10)
C310.0504 (13)0.0345 (11)0.0393 (12)0.0002 (10)0.0042 (10)0.0089 (9)
C320.0467 (13)0.0412 (12)0.0347 (11)0.0022 (10)0.0078 (10)0.0043 (9)
C330.0373 (11)0.0322 (11)0.0376 (11)0.0082 (9)0.0062 (9)0.0010 (9)
C340.0341 (11)0.0319 (11)0.0421 (12)0.0010 (9)0.0102 (9)0.0058 (9)
C350.0385 (12)0.0410 (12)0.0406 (12)0.0008 (10)0.0051 (10)0.0083 (10)
C360.0417 (12)0.0410 (13)0.0492 (13)0.0006 (10)0.0081 (10)0.0005 (10)
Geometric parameters (Å, º) top
O1—C61.237 (2)C14—C151.382 (3)
O2—C241.233 (2)C14—H140.95
O3—H3C0.85 (1)C15—H150.95
O3—H3D0.84 (1)C17—H17A0.98
N1—C11.367 (2)C17—H17B0.98
N1—C51.380 (2)C17—H17C0.98
N1—H10.88C18—H18A0.98
N2—C161.154 (2)C18—H18B0.98
N3—C51.343 (2)C18—H18C0.98
N3—H3A0.88C19—C201.358 (3)
N3—H3B0.88C19—C271.495 (3)
N4—C191.366 (2)C20—C241.448 (3)
N4—C231.378 (3)C20—C211.517 (3)
N4—H40.88C21—C221.521 (3)
N5—C341.155 (3)C21—C281.525 (3)
N6—C231.352 (2)C21—H211.00
N6—H6A0.88C22—C231.367 (3)
N6—H6B0.88C22—C341.413 (3)
C1—C21.353 (3)C24—C251.501 (3)
C1—C91.502 (2)C25—C261.531 (3)
C2—C61.443 (3)C25—H25A0.99
C2—C31.516 (2)C25—H25B0.99
C3—C41.524 (2)C26—C361.527 (3)
C3—C101.528 (3)C26—C351.528 (3)
C3—H31.00C26—C271.531 (3)
C4—C51.363 (3)C27—H27A0.99
C4—C161.411 (3)C27—H27B0.99
C6—C71.510 (3)C28—C291.392 (3)
C7—C81.525 (3)C28—C331.392 (3)
C7—H7A0.99C29—C301.388 (3)
C7—H7B0.99C29—H290.95
C8—C171.524 (3)C30—C311.372 (3)
C8—C91.530 (3)C30—H300.95
C8—C181.533 (3)C31—C321.384 (3)
C9—H9A0.99C31—H310.95
C9—H9B0.99C32—C331.377 (3)
C10—C111.392 (3)C32—H320.95
C10—C151.394 (3)C33—H330.95
C11—C121.384 (3)C35—H35A0.98
C11—H110.95C35—H35B0.98
C12—C131.382 (3)C35—H35C0.98
C12—H120.95C36—H36A0.98
C13—C141.376 (3)C36—H36B0.98
C13—H130.95C36—H36C0.98
H3C—O3—H3D113 (2)C8—C18—H18A109.5
C1—N1—C5122.01 (16)C8—C18—H18B109.5
C1—N1—H1119.0H18A—C18—H18B109.5
C5—N1—H1119.0C8—C18—H18C109.5
C5—N3—H3A120.0H18A—C18—H18C109.5
C5—N3—H3B120.0H18B—C18—H18C109.5
H3A—N3—H3B120.0C20—C19—N4121.20 (18)
C19—N4—C23121.66 (16)C20—C19—C27123.54 (18)
C19—N4—H4119.2N4—C19—C27115.25 (16)
C23—N4—H4119.2C19—C20—C24119.07 (18)
C23—N6—H6A120.0C19—C20—C21122.06 (17)
C23—N6—H6B120.0C24—C20—C21118.59 (16)
H6A—N6—H6B120.0C20—C21—C22108.99 (15)
C2—C1—N1121.37 (16)C20—C21—C28109.88 (15)
C2—C1—C9124.53 (17)C22—C21—C28112.41 (16)
N1—C1—C9114.10 (16)C20—C21—H21108.5
C1—C2—C6118.81 (16)C22—C21—H21108.5
C1—C2—C3121.64 (16)C28—C21—H21108.5
C6—C2—C3119.49 (16)C23—C22—C34117.71 (18)
C2—C3—C4109.30 (14)C23—C22—C21122.23 (17)
C2—C3—C10113.40 (15)C34—C22—C21119.93 (17)
C4—C3—C10110.18 (14)N6—C23—C22125.11 (19)
C2—C3—H3107.9N6—C23—N4114.84 (17)
C4—C3—H3107.9C22—C23—N4120.05 (17)
C10—C3—H3107.9O2—C24—C20121.13 (19)
C5—C4—C16118.50 (17)O2—C24—C25119.87 (18)
C5—C4—C3122.68 (16)C20—C24—C25118.99 (17)
C16—C4—C3118.56 (16)C24—C25—C26115.00 (16)
N3—C5—C4126.75 (17)C24—C25—H25A108.5
N3—C5—N1113.99 (17)C26—C25—H25A108.5
C4—C5—N1119.26 (17)C24—C25—H25B108.5
O1—C6—C2121.66 (17)C26—C25—H25B108.5
O1—C6—C7119.55 (17)H25A—C25—H25B107.5
C2—C6—C7118.72 (16)C36—C26—C35108.58 (18)
C6—C7—C8114.73 (16)C36—C26—C27110.22 (16)
C6—C7—H7A108.6C35—C26—C27110.47 (17)
C8—C7—H7A108.6C36—C26—C25110.16 (17)
C6—C7—H7B108.6C35—C26—C25110.38 (17)
C8—C7—H7B108.6C27—C26—C25107.02 (17)
H7A—C7—H7B107.6C19—C27—C26112.93 (16)
C17—C8—C7110.41 (18)C19—C27—H27A109.0
C17—C8—C9110.94 (17)C26—C27—H27A109.0
C7—C8—C9107.91 (16)C19—C27—H27B109.0
C17—C8—C18109.04 (18)C26—C27—H27B109.0
C7—C8—C18109.71 (17)H27A—C27—H27B107.8
C9—C8—C18108.80 (17)C29—C28—C33117.87 (18)
C1—C9—C8113.25 (16)C29—C28—C21121.66 (18)
C1—C9—H9A108.9C33—C28—C21120.46 (17)
C8—C9—H9A108.9C30—C29—C28120.7 (2)
C1—C9—H9B108.9C30—C29—H29119.6
C8—C9—H9B108.9C28—C29—H29119.6
H9A—C9—H9B107.7C31—C30—C29120.2 (2)
C11—C10—C15118.09 (18)C31—C30—H30119.9
C11—C10—C3121.64 (17)C29—C30—H30119.9
C15—C10—C3120.15 (17)C30—C31—C32120.0 (2)
C12—C11—C10120.9 (2)C30—C31—H31120.0
C12—C11—H11119.6C32—C31—H31120.0
C10—C11—H11119.6C33—C32—C31119.7 (2)
C13—C12—C11120.1 (2)C33—C32—H32120.2
C13—C12—H12120.0C31—C32—H32120.2
C11—C12—H12120.0C32—C33—C28121.51 (19)
C14—C13—C12119.9 (2)C32—C33—H33119.2
C14—C13—H13120.1C28—C33—H33119.2
C12—C13—H13120.1N5—C34—C22177.4 (2)
C13—C14—C15120.2 (2)C26—C35—H35A109.5
C13—C14—H14119.9C26—C35—H35B109.5
C15—C14—H14119.9H35A—C35—H35B109.5
C14—C15—C10120.9 (2)C26—C35—H35C109.5
C14—C15—H15119.5H35A—C35—H35C109.5
C10—C15—H15119.5H35B—C35—H35C109.5
N2—C16—C4178.6 (2)C26—C36—H36A109.5
C8—C17—H17A109.5C26—C36—H36B109.5
C8—C17—H17B109.5H36A—C36—H36B109.5
H17A—C17—H17B109.5C26—C36—H36C109.5
C8—C17—H17C109.5H36A—C36—H36C109.5
H17A—C17—H17C109.5H36B—C36—H36C109.5
H17B—C17—H17C109.5
C5—N1—C1—C29.4 (3)C23—N4—C19—C207.6 (3)
C5—N1—C1—C9169.95 (17)C23—N4—C19—C27172.55 (17)
N1—C1—C2—C6171.40 (17)N4—C19—C20—C24179.08 (17)
C9—C1—C2—C67.9 (3)C27—C19—C20—C241.1 (3)
N1—C1—C2—C35.9 (3)N4—C19—C20—C217.0 (3)
C9—C1—C2—C3174.78 (17)C27—C19—C20—C21172.83 (17)
C1—C2—C3—C418.8 (2)C19—C20—C21—C2219.5 (2)
C6—C2—C3—C4158.48 (16)C24—C20—C21—C22166.53 (16)
C1—C2—C3—C10104.5 (2)C19—C20—C21—C28104.0 (2)
C6—C2—C3—C1078.2 (2)C24—C20—C21—C2869.9 (2)
C2—C3—C4—C519.7 (2)C20—C21—C22—C2320.6 (3)
C10—C3—C4—C5105.5 (2)C28—C21—C22—C23101.4 (2)
C2—C3—C4—C16166.21 (16)C20—C21—C22—C34163.59 (18)
C10—C3—C4—C1668.5 (2)C28—C21—C22—C3474.3 (2)
C16—C4—C5—N31.3 (3)C34—C22—C23—N65.0 (3)
C3—C4—C5—N3172.74 (19)C21—C22—C23—N6170.89 (18)
C16—C4—C5—N1178.52 (17)C34—C22—C23—N4174.98 (18)
C3—C4—C5—N17.4 (3)C21—C22—C23—N49.2 (3)
C1—N1—C5—N3171.30 (18)C19—N4—C23—N6173.50 (17)
C1—N1—C5—C48.6 (3)C19—N4—C23—C226.5 (3)
C1—C2—C6—O1173.83 (18)C19—C20—C24—O2179.16 (18)
C3—C2—C6—O13.6 (3)C21—C20—C24—O26.7 (3)
C1—C2—C6—C73.1 (3)C19—C20—C24—C251.6 (3)
C3—C2—C6—C7179.48 (17)C21—C20—C24—C25172.48 (16)
O1—C6—C7—C8154.59 (18)O2—C24—C25—C26152.65 (18)
C2—C6—C7—C828.4 (3)C20—C24—C25—C2626.6 (3)
C6—C7—C8—C1769.5 (2)C24—C25—C26—C36171.27 (17)
C6—C7—C8—C951.9 (2)C24—C25—C26—C3568.8 (2)
C6—C7—C8—C18170.33 (18)C24—C25—C26—C2751.4 (2)
C2—C1—C9—C818.9 (3)C20—C19—C27—C2627.3 (3)
N1—C1—C9—C8161.77 (17)N4—C19—C27—C26152.59 (17)
C17—C8—C9—C174.4 (2)C36—C26—C27—C19170.71 (17)
C7—C8—C9—C146.7 (2)C35—C26—C27—C1969.3 (2)
C18—C8—C9—C1165.63 (18)C25—C26—C27—C1950.9 (2)
C2—C3—C10—C1135.0 (2)C20—C21—C28—C29121.93 (19)
C4—C3—C10—C1187.9 (2)C22—C21—C28—C29116.5 (2)
C2—C3—C10—C15149.16 (17)C20—C21—C28—C3356.5 (2)
C4—C3—C10—C1588.0 (2)C22—C21—C28—C3365.1 (2)
C15—C10—C11—C120.2 (3)C33—C28—C29—C300.7 (3)
C3—C10—C11—C12176.16 (18)C21—C28—C29—C30177.80 (19)
C10—C11—C12—C130.3 (3)C28—C29—C30—C310.3 (3)
C11—C12—C13—C140.3 (3)C29—C30—C31—C320.9 (3)
C12—C13—C14—C150.3 (3)C30—C31—C32—C330.6 (3)
C13—C14—C15—C100.8 (3)C31—C32—C33—C280.4 (3)
C11—C10—C15—C140.8 (3)C29—C28—C33—C321.0 (3)
C3—C10—C15—C14176.77 (18)C21—C28—C33—C32177.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.882.142.892 (2)144
N3—H3A···N2ii0.882.152.990 (2)159
N3—H3B···O2i0.882.142.927 (2)148
O3—H3C···O10.85 (1)2.02 (2)2.763 (2)146 (3)
O3—H3D···N5iii0.84 (1)2.16 (2)2.935 (3)152 (3)
N4—H4···O3i0.881.872.744 (2)174
N6—H6B···O1i0.882.092.911 (2)156
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1, z+1; (iii) x+2, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds