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The title compound, C13H14ClN7, crystallizes with two independent mol­ecules in the asymmetric unit, with little conformational difference between them. The triazole ring is almost coplanar with the pyrimidine ring. Intra­molecular C—H...N and inter­molecular C—H...N and N—H...N hydrogen-bonding inter­actions contribute to the stability of the structure. In addition, weak C—H...π hydrogen-bonding and strong π–π stacking inter­actions are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039171/at2121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039171/at2121Isup2.hkl
Contains datablock I

CCDC reference: 627296

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.063
  • wR factor = 0.185
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C12
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.97 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 6 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(6-Chloropyridin-3-ylmethyl)-6-propyl-6,7-dihydro-3H-1,2,3- triazolo[4,5-d]pyrimidin-7-imine top
Crystal data top
C13H14ClN7Z = 4
Mr = 303.76F(000) = 632
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1644 (9) ÅCell parameters from 3445 reflections
b = 13.1572 (16) Åθ = 2.6–26.7°
c = 15.6765 (19) ŵ = 0.27 mm1
α = 91.008 (2)°T = 298 K
β = 99.321 (2)°Plate, colourless
γ = 96.281 (2)°0.36 × 0.20 × 0.06 mm
V = 1448.5 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
φ and ω scansh = 88
8283 measured reflectionsk = 1515
5029 independent reflectionsl = 1418
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0964P)2 + 0.678P]
where P = (Fo2 + 2Fc2)/3
5029 reflections(Δ/σ)max < 0.001
384 parametersΔρmax = 0.50 e Å3
2 restraintsΔρmin = 0.43 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
C10.2421 (4)0.13915 (19)0.22453 (18)0.0483 (7)
C20.2734 (6)0.1178 (3)0.1419 (2)0.0697 (9)
H20.39290.10390.13220.084*
C30.1252 (7)0.1174 (3)0.0742 (2)0.0806 (11)
H30.14240.10380.01780.097*
C40.0473 (6)0.1373 (2)0.0916 (2)0.0670 (9)
C50.0623 (5)0.1589 (2)0.23316 (19)0.0600 (8)
H50.04040.17410.28860.072*
C60.3969 (4)0.1421 (2)0.30182 (18)0.0523 (7)
H6A0.51290.12530.28320.063*
H6B0.42130.21090.32730.063*
C70.2961 (3)0.08996 (18)0.44410 (16)0.0391 (6)
C80.2660 (3)0.00361 (17)0.47875 (16)0.0366 (5)
C90.2110 (3)0.01297 (18)0.56287 (16)0.0389 (6)
C100.2265 (4)0.17310 (19)0.55525 (19)0.0490 (7)
H100.20980.23330.58370.059*
C110.1423 (4)0.0936 (2)0.68451 (19)0.0558 (7)
H11A0.06290.14870.68530.067*
H11B0.06620.03070.69460.067*
C120.3011 (7)0.1122 (5)0.7553 (3)0.122 (2)
H12A0.38480.17100.74250.146*
H12B0.37280.05350.75880.146*
C130.2436 (7)0.1312 (4)0.8419 (3)0.1106 (16)
H13A0.16160.18460.83760.166*
H13B0.35520.15160.88400.166*
H13C0.17740.06970.85940.166*
C140.3600 (4)0.62323 (19)0.80702 (18)0.0499 (7)
C150.3335 (6)0.6294 (3)0.8919 (2)0.0698 (9)
H150.21310.63480.90540.084*
C160.4883 (7)0.6274 (3)0.9567 (2)0.0821 (11)
H160.47520.63141.01470.098*
C170.6611 (6)0.6194 (2)0.9328 (2)0.0691 (9)
C180.5418 (5)0.6147 (2)0.79213 (19)0.0545 (7)
H180.56090.61060.73490.065*
C190.1959 (4)0.6280 (2)0.73455 (18)0.0531 (7)
H19A0.07760.60890.75580.064*
H19B0.19530.69780.71570.064*
C200.2321 (4)0.58421 (18)0.58003 (17)0.0405 (6)
C210.2320 (3)0.49217 (18)0.53819 (16)0.0391 (6)
C220.2627 (4)0.48746 (18)0.44971 (17)0.0413 (6)
C230.2789 (4)0.6733 (2)0.4675 (2)0.0533 (7)
H230.29600.73530.44050.064*
C240.3081 (6)0.5959 (3)0.3272 (2)0.0674 (9)
H24A0.44270.59550.32530.081*
H24B0.24220.53470.29580.081*
C250.2455 (8)0.6829 (3)0.2813 (3)0.0998 (14)
H25A0.31810.74500.30830.120*
H25B0.11230.68680.28430.120*
C260.2719 (9)0.6744 (4)0.1863 (2)0.1165 (18)
H26A0.40390.67090.18340.175*
H26B0.23070.73330.15670.175*
H26C0.19770.61370.15930.175*
Cl10.2405 (2)0.13351 (9)0.00703 (7)0.1122 (5)
Cl20.85935 (19)0.61704 (10)1.01450 (7)0.1096 (4)
N10.0844 (4)0.1579 (2)0.16830 (18)0.0722 (8)
N20.3474 (3)0.07072 (15)0.36722 (14)0.0425 (5)
N30.3477 (3)0.03175 (15)0.35419 (14)0.0449 (5)
N40.2986 (3)0.07707 (15)0.42239 (13)0.0410 (5)
N50.1944 (3)0.08556 (15)0.59784 (14)0.0441 (5)
N60.2776 (3)0.18324 (15)0.47982 (15)0.0481 (6)
N70.1767 (3)0.09161 (16)0.60640 (14)0.0466 (5)
H70.19580.14570.57900.056*
N80.6928 (4)0.6118 (2)0.85407 (18)0.0639 (7)
N90.2053 (3)0.56058 (15)0.66061 (14)0.0456 (5)
N100.1872 (4)0.45739 (16)0.66851 (15)0.0526 (6)
N110.2049 (3)0.41570 (15)0.59325 (15)0.0478 (6)
N120.2818 (3)0.58796 (16)0.41792 (14)0.0468 (5)
N130.2552 (3)0.67950 (16)0.54768 (15)0.0510 (6)
N140.2744 (4)0.41123 (17)0.40056 (16)0.0534 (6)
H140.265 (5)0.3553 (15)0.4277 (18)0.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0667 (18)0.0349 (13)0.0488 (16)0.0113 (12)0.0214 (13)0.0084 (11)
C20.088 (3)0.072 (2)0.058 (2)0.0226 (18)0.0275 (18)0.0010 (16)
C30.129 (4)0.077 (2)0.0405 (18)0.029 (2)0.018 (2)0.0045 (15)
C40.096 (3)0.0543 (18)0.0498 (18)0.0229 (17)0.0005 (17)0.0035 (14)
C50.074 (2)0.071 (2)0.0397 (16)0.0266 (16)0.0111 (14)0.0085 (14)
C60.0600 (18)0.0438 (15)0.0557 (17)0.0034 (12)0.0178 (14)0.0121 (12)
C70.0369 (13)0.0349 (12)0.0447 (14)0.0055 (10)0.0034 (11)0.0021 (10)
C80.0348 (13)0.0308 (12)0.0437 (14)0.0052 (9)0.0038 (10)0.0013 (10)
C90.0340 (13)0.0361 (13)0.0451 (14)0.0050 (10)0.0016 (10)0.0000 (11)
C100.0533 (17)0.0360 (14)0.0583 (18)0.0070 (11)0.0103 (13)0.0064 (12)
C110.0635 (19)0.0519 (16)0.0537 (17)0.0024 (13)0.0182 (14)0.0088 (13)
C120.078 (3)0.221 (6)0.059 (2)0.005 (3)0.011 (2)0.041 (3)
C130.126 (4)0.142 (4)0.062 (2)0.008 (3)0.028 (3)0.033 (3)
C140.0691 (19)0.0356 (13)0.0476 (16)0.0071 (12)0.0177 (14)0.0047 (11)
C150.085 (2)0.073 (2)0.058 (2)0.0175 (18)0.0289 (18)0.0042 (16)
C160.114 (3)0.094 (3)0.0413 (18)0.025 (2)0.015 (2)0.0019 (17)
C170.087 (3)0.0541 (18)0.063 (2)0.0104 (16)0.0027 (18)0.0010 (15)
C180.073 (2)0.0450 (15)0.0473 (16)0.0056 (13)0.0164 (15)0.0030 (12)
C190.0648 (19)0.0434 (15)0.0541 (17)0.0099 (13)0.0172 (14)0.0085 (12)
C200.0400 (14)0.0356 (13)0.0459 (15)0.0049 (10)0.0076 (11)0.0054 (11)
C210.0348 (13)0.0350 (13)0.0465 (14)0.0034 (10)0.0049 (11)0.0040 (11)
C220.0392 (14)0.0368 (13)0.0474 (15)0.0065 (10)0.0049 (11)0.0039 (11)
C230.0653 (19)0.0368 (14)0.0594 (18)0.0078 (12)0.0130 (14)0.0035 (12)
C240.090 (2)0.0650 (19)0.0539 (19)0.0268 (17)0.0190 (17)0.0061 (15)
C250.135 (4)0.097 (3)0.075 (3)0.030 (3)0.028 (3)0.028 (2)
C260.189 (5)0.096 (3)0.055 (2)0.004 (3)0.006 (3)0.025 (2)
Cl10.1476 (11)0.1037 (8)0.0731 (7)0.0401 (7)0.0350 (7)0.0077 (6)
Cl20.1169 (10)0.1169 (9)0.0828 (8)0.0198 (7)0.0244 (6)0.0034 (6)
N10.083 (2)0.0827 (19)0.0542 (17)0.0333 (15)0.0039 (14)0.0095 (14)
N20.0460 (12)0.0349 (11)0.0477 (13)0.0063 (9)0.0095 (10)0.0062 (9)
N30.0496 (13)0.0378 (11)0.0487 (13)0.0063 (9)0.0116 (10)0.0006 (9)
N40.0448 (12)0.0333 (10)0.0452 (12)0.0060 (9)0.0071 (9)0.0033 (9)
N50.0492 (13)0.0363 (11)0.0473 (13)0.0052 (9)0.0096 (10)0.0038 (9)
N60.0558 (14)0.0302 (11)0.0585 (15)0.0054 (9)0.0098 (11)0.0009 (10)
N70.0560 (14)0.0362 (11)0.0487 (13)0.0047 (10)0.0125 (11)0.0027 (10)
N80.0725 (18)0.0578 (15)0.0606 (17)0.0082 (13)0.0084 (14)0.0007 (12)
N90.0537 (13)0.0350 (11)0.0491 (13)0.0071 (9)0.0106 (10)0.0062 (9)
N100.0665 (16)0.0376 (12)0.0553 (14)0.0048 (10)0.0157 (12)0.0030 (10)
N110.0580 (14)0.0345 (11)0.0513 (13)0.0035 (9)0.0116 (11)0.0038 (10)
N120.0547 (14)0.0397 (12)0.0472 (13)0.0105 (10)0.0093 (10)0.0006 (9)
N130.0643 (15)0.0350 (12)0.0545 (15)0.0076 (10)0.0118 (12)0.0046 (10)
N140.0687 (16)0.0419 (13)0.0515 (14)0.0098 (11)0.0135 (12)0.0051 (11)
Geometric parameters (Å, º) top
C1—C51.369 (4)C15—C161.381 (5)
C1—C21.379 (4)C15—H150.9300
C1—C61.501 (4)C16—C171.365 (6)
C2—C31.374 (5)C16—H160.9300
C2—H20.9300C17—N81.294 (4)
C3—C41.359 (5)C17—Cl21.755 (4)
C3—H30.9300C18—N81.336 (4)
C4—N11.302 (4)C18—H180.9300
C4—Cl11.751 (4)C19—N91.462 (3)
C5—N11.338 (4)C19—H19A0.9700
C5—H50.9300C19—H19B0.9700
C6—N21.462 (3)C20—N91.345 (3)
C6—H6A0.9700C20—N131.364 (3)
C6—H6B0.9700C20—C211.367 (3)
C7—N21.344 (3)C21—N111.355 (3)
C7—C81.364 (3)C21—C221.440 (3)
C7—N61.368 (3)C22—N141.272 (3)
C8—N41.362 (3)C22—N121.422 (3)
C8—C91.440 (3)C23—N131.298 (4)
C9—N71.273 (3)C23—N121.359 (3)
C9—N51.423 (3)C23—H230.9300
C10—N61.298 (3)C24—C251.438 (5)
C10—N51.358 (3)C24—N121.468 (4)
C10—H100.9300C24—H24A0.9700
C11—C121.451 (5)C24—H24B0.9700
C11—N51.471 (3)C25—C261.535 (6)
C11—H11A0.9700C25—H25A0.9700
C11—H11B0.9700C25—H25B0.9700
C12—C131.506 (5)C26—H26A0.9600
C12—H12A0.9700C26—H26B0.9600
C12—H12B0.9700C26—H26C0.9600
C13—H13A0.9600N2—N31.360 (3)
C13—H13B0.9600N3—N41.312 (3)
C13—H13C0.9600N7—H70.8595
C14—C181.376 (4)N9—N101.359 (3)
C14—C151.377 (4)N10—N111.323 (3)
C14—C191.505 (4)N14—H140.858 (10)
C5—C1—C2116.8 (3)C16—C17—Cl2118.2 (3)
C5—C1—C6121.0 (3)N8—C18—C14124.6 (3)
C2—C1—C6122.2 (3)N8—C18—H18117.7
C3—C2—C1118.9 (3)C14—C18—H18117.7
C3—C2—H2120.5N9—C19—C14112.5 (2)
C1—C2—H2120.5N9—C19—H19A109.1
C4—C3—C2118.5 (3)C14—C19—H19A109.1
C4—C3—H3120.8N9—C19—H19B109.1
C2—C3—H3120.8C14—C19—H19B109.1
N1—C4—C3125.1 (3)H19A—C19—H19B107.8
N1—C4—Cl1115.5 (3)N9—C20—N13127.2 (2)
C3—C4—Cl1119.4 (3)N9—C20—C21104.9 (2)
N1—C5—C1125.3 (3)N13—C20—C21127.8 (2)
N1—C5—H5117.4N11—C21—C20109.3 (2)
C1—C5—H5117.4N11—C21—C22129.9 (2)
N2—C6—C1112.3 (2)C20—C21—C22120.7 (2)
N2—C6—H6A109.1N14—C22—N12119.6 (2)
C1—C6—H6A109.1N14—C22—C21130.7 (2)
N2—C6—H6B109.1N12—C22—C21109.7 (2)
C1—C6—H6B109.1N13—C23—N12128.3 (3)
H6A—C6—H6B107.9N13—C23—H23115.9
N2—C7—C8105.1 (2)N12—C23—H23115.9
N2—C7—N6127.4 (2)C25—C24—N12117.9 (3)
C8—C7—N6127.5 (2)C25—C24—H24A107.8
N4—C8—C7109.1 (2)N12—C24—H24A107.8
N4—C8—C9130.1 (2)C25—C24—H24B107.8
C7—C8—C9120.9 (2)N12—C24—H24B107.8
N7—C9—N5119.3 (2)H24A—C24—H24B107.2
N7—C9—C8130.8 (2)C24—C25—C26110.5 (4)
N5—C9—C8109.9 (2)C24—C25—H25A109.6
N6—C10—N5128.1 (2)C26—C25—H25A109.6
N6—C10—H10116.0C24—C25—H25B109.6
N5—C10—H10116.0C26—C25—H25B109.6
C12—C11—N5115.3 (3)H25A—C25—H25B108.1
C12—C11—H11A108.4C25—C26—H26A109.5
N5—C11—H11A108.4C25—C26—H26B109.5
C12—C11—H11B108.4H26A—C26—H26B109.5
N5—C11—H11B108.4C25—C26—H26C109.5
H11A—C11—H11B107.5H26A—C26—H26C109.5
C11—C12—C13114.1 (4)H26B—C26—H26C109.5
C11—C12—H12A108.7C4—N1—C5115.5 (3)
C13—C12—H12A108.7C7—N2—N3110.02 (19)
C11—C12—H12B108.7C7—N2—C6129.4 (2)
C13—C12—H12B108.7N3—N2—C6120.6 (2)
H12A—C12—H12B107.6N4—N3—N2107.75 (19)
C12—C13—H13A109.5N3—N4—C8108.07 (19)
C12—C13—H13B109.5C10—N5—C9123.0 (2)
H13A—C13—H13B109.5C10—N5—C11118.2 (2)
C12—C13—H13C109.5C9—N5—C11118.8 (2)
H13A—C13—H13C109.5C10—N6—C7110.7 (2)
H13B—C13—H13C109.5C9—N7—H7110.0
C18—C14—C15117.2 (3)C17—N8—C18115.9 (3)
C18—C14—C19122.2 (3)C20—N9—N10110.2 (2)
C15—C14—C19120.5 (3)C20—N9—C19129.6 (2)
C14—C15—C16119.0 (3)N10—N9—C19120.1 (2)
C14—C15—H15120.5N11—N10—N9107.4 (2)
C16—C15—H15120.5N10—N11—C21108.1 (2)
C17—C16—C15117.7 (3)C23—N12—C22123.1 (2)
C17—C16—H16121.2C23—N12—C24120.6 (2)
C15—C16—H16121.2C22—N12—C24116.3 (2)
N8—C17—C16125.6 (3)C23—N13—C20110.4 (2)
N8—C17—Cl2116.1 (3)C22—N14—H14111 (2)
C5—C1—C2—C30.1 (5)C1—C6—N2—C7106.0 (3)
C6—C1—C2—C3179.4 (3)C1—C6—N2—N373.5 (3)
C1—C2—C3—C40.5 (5)C7—N2—N3—N40.5 (3)
C2—C3—C4—N10.5 (6)C6—N2—N3—N4180.0 (2)
C2—C3—C4—Cl1178.1 (3)N2—N3—N4—C80.3 (3)
C2—C1—C5—N10.7 (5)C7—C8—N4—N30.0 (3)
C6—C1—C5—N1179.9 (3)C9—C8—N4—N3179.2 (2)
C5—C1—C6—N258.0 (3)N6—C10—N5—C90.9 (4)
C2—C1—C6—N2122.6 (3)N6—C10—N5—C11178.4 (3)
N2—C7—C8—N40.3 (3)N7—C9—N5—C10179.3 (2)
N6—C7—C8—N4179.6 (2)C8—C9—N5—C100.2 (3)
N2—C7—C8—C9179.0 (2)N7—C9—N5—C111.5 (3)
N6—C7—C8—C91.1 (4)C8—C9—N5—C11179.0 (2)
N4—C8—C9—N70.8 (4)C12—C11—N5—C1085.9 (4)
C7—C8—C9—N7179.9 (3)C12—C11—N5—C993.4 (4)
N4—C8—C9—N5179.8 (2)N5—C10—N6—C70.5 (4)
C7—C8—C9—N50.6 (3)N2—C7—N6—C10179.7 (2)
N5—C11—C12—C13173.8 (4)C8—C7—N6—C100.5 (4)
C18—C14—C15—C160.4 (5)C16—C17—N8—C181.7 (5)
C19—C14—C15—C16178.3 (3)Cl2—C17—N8—C18179.3 (2)
C14—C15—C16—C170.0 (5)C14—C18—N8—C171.2 (4)
C15—C16—C17—N81.2 (6)N13—C20—N9—N10179.7 (2)
C15—C16—C17—Cl2179.9 (3)C21—C20—N9—N100.6 (3)
C15—C14—C18—N80.1 (4)N13—C20—N9—C190.8 (4)
C19—C14—C18—N8178.9 (3)C21—C20—N9—C19178.9 (3)
C18—C14—C19—N938.1 (4)C14—C19—N9—C20113.6 (3)
C15—C14—C19—N9143.2 (3)C14—C19—N9—N1065.9 (3)
N9—C20—C21—N110.2 (3)C20—N9—N10—N110.8 (3)
N13—C20—C21—N11179.9 (2)C19—N9—N10—N11178.8 (2)
N9—C20—C21—C22178.3 (2)N9—N10—N11—C210.6 (3)
N13—C20—C21—C221.4 (4)C20—C21—N11—N100.3 (3)
N11—C21—C22—N140.8 (5)C22—C21—N11—N10178.6 (3)
C20—C21—C22—N14177.3 (3)N13—C23—N12—C221.6 (5)
N11—C21—C22—N12179.4 (2)N13—C23—N12—C24179.2 (3)
C20—C21—C22—N122.5 (3)N14—C22—N12—C23177.2 (3)
N12—C24—C25—C26176.2 (4)C21—C22—N12—C232.6 (3)
C3—C4—N1—C50.1 (5)N14—C22—N12—C242.0 (4)
Cl1—C4—N1—C5178.7 (2)C21—C22—N12—C24178.2 (2)
C1—C5—N1—C40.7 (5)C25—C24—N12—C2327.9 (5)
C8—C7—N2—N30.5 (3)C25—C24—N12—C22152.9 (4)
N6—C7—N2—N3179.4 (2)N12—C23—N13—C200.2 (4)
C8—C7—N2—C6179.9 (2)N9—C20—N13—C23179.6 (3)
N6—C7—N2—C60.1 (4)C21—C20—N13—C230.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N4i0.932.493.364 (3)157
C18—H18···N14ii0.932.623.511 (4)161
C10—H10···N110.932.413.262 (3)153
C5—H5···N7iii0.932.613.344 (4)136
N14—H14···N60.86 (1)2.43 (1)3.268 (3)167 (3)
N7—H7···N13iv0.862.443.267 (3)162
C11—H11B···Cg1iii0.972.943.478 (1)116
C24—H24A···Cg2ii0.972.963.792 (4)145
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x, y1, z.
 

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