Download citation
Download citation
link to html
The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1,12-diazido-n-dodecane in the presence of catalysts leads to the formation of the title compound, C38H46N8O2. The seven-membered diazepinyl ring adopts a boat conformation with the azido­dodecyl­triazolylmethyl-bearing C atom as the prow and the fused-ring C atoms as the stern. The octyltriazolylmethyl substituent occupies an axial position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809054464/bt5146sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809054464/bt5146Isup2.hkl
Contains datablock I

CCDC reference: 766878

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.147
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT793_ALERT_4_G The Model has Chirality at C8 (Verify) .... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Related literature top

For the crystal structures of other N-substituted homologs, see: Jabli et al. (2009, 2010).

Experimental top

To a solution 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione (1 mmol) t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and 1,12-diazido-n-dodecaneoctane (5 mmol). Stirring was continued for 12 h. The solution was diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 x 20 ml). The extracts were washed with brine and dried over sodium sulfate. The compound was recrystallized from ethyl acetate/ether to give colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C38H46N8O2 at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.
1-(12-Azido-n-dodecyl)-4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl)methyl]-1H-1,2,3-triazole top
Crystal data top
C38H46N8O2Z = 2
Mr = 646.83F(000) = 692
Triclinic, P1Dx = 1.214 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4269 (2) ÅCell parameters from 3120 reflections
b = 12.3304 (3) Åθ = 2.3–22.9°
c = 15.5500 (4) ŵ = 0.08 mm1
α = 101.121 (2)°T = 193 K
β = 92.175 (2)°Plate, colorless
γ = 92.935 (2)°0.40 × 0.20 × 0.06 mm
V = 1769.11 (7) Å3
Data collection top
Bruker APEXII
diffractometer
4315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.076
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ϕ and ω scansh = 1212
33681 measured reflectionsk = 1616
8126 independent reflectionsl = 2020
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0087P]
where P = (Fo2 + 2Fc2)/3
8126 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C38H46N8O2γ = 92.935 (2)°
Mr = 646.83V = 1769.11 (7) Å3
Triclinic, P1Z = 2
a = 9.4269 (2) ÅMo Kα radiation
b = 12.3304 (3) ŵ = 0.08 mm1
c = 15.5500 (4) ÅT = 193 K
α = 101.121 (2)°0.40 × 0.20 × 0.06 mm
β = 92.175 (2)°
Data collection top
Bruker APEXII
diffractometer
4315 reflections with I > 2σ(I)
33681 measured reflectionsRint = 0.076
8126 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
8126 reflectionsΔρmin = 0.22 e Å3
433 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49525 (16)1.12343 (12)0.23925 (10)0.0408 (4)
O20.51737 (15)0.90533 (11)0.37285 (9)0.0367 (4)
N10.27355 (18)1.11470 (12)0.29224 (11)0.0297 (4)
N20.28200 (18)0.93241 (13)0.38543 (11)0.0290 (4)
N30.3838 (2)0.70440 (15)0.17514 (14)0.0477 (5)
N40.4145 (2)0.60090 (15)0.17564 (15)0.0535 (6)
N50.5564 (2)0.60077 (14)0.18490 (13)0.0429 (5)
N61.0314 (2)0.65890 (16)0.19426 (15)0.0516 (6)
N70.9694 (2)0.73485 (17)0.16605 (13)0.0433 (5)
N80.9271 (2)0.81025 (18)0.14108 (15)0.0553 (6)
C10.1478 (2)1.05032 (15)0.30484 (13)0.0283 (5)
C20.0170 (2)1.07803 (17)0.27332 (14)0.0353 (5)
H20.01391.13620.24130.042*
C30.1078 (2)1.02300 (18)0.28764 (15)0.0405 (6)
H30.19601.04320.26570.049*
C40.1046 (2)0.93793 (18)0.33418 (15)0.0377 (5)
H40.19060.90030.34490.045*
C50.0246 (2)0.90793 (17)0.36500 (14)0.0340 (5)
H50.02670.84900.39630.041*
C60.1516 (2)0.96343 (15)0.35062 (13)0.0278 (5)
C70.3922 (2)1.06848 (16)0.25614 (13)0.0297 (5)
C80.3893 (2)0.94297 (15)0.24558 (13)0.0271 (5)
H80.29520.90990.21830.033*
C90.4037 (2)0.92453 (15)0.33936 (13)0.0288 (5)
C100.2720 (2)1.23642 (15)0.31792 (14)0.0345 (5)
H10A0.20541.26410.27750.041*
H10B0.36821.27000.31260.041*
C110.2275 (2)1.27102 (15)0.41053 (14)0.0286 (5)
C120.1029 (2)1.32471 (17)0.42944 (15)0.0364 (5)
H120.04351.33950.38280.044*
C130.0643 (3)1.35682 (18)0.51513 (17)0.0452 (6)
H130.02121.39330.52710.054*
C140.1498 (3)1.33594 (18)0.58312 (16)0.0459 (6)
H140.12361.35840.64200.055*
C150.2740 (3)1.28227 (18)0.56568 (15)0.0415 (6)
H150.33321.26780.61250.050*
C160.3115 (2)1.24989 (16)0.48007 (14)0.0343 (5)
H160.39641.21240.46840.041*
C170.2891 (2)0.91041 (17)0.47532 (13)0.0333 (5)
H17A0.20300.93740.50500.040*
H17B0.37230.95380.50790.040*
C180.3006 (2)0.78970 (17)0.48126 (14)0.0310 (5)
C190.3054 (2)0.70492 (17)0.40862 (15)0.0379 (5)
H190.29730.72070.35130.046*
C200.3221 (2)0.59694 (18)0.41938 (17)0.0451 (6)
H200.32640.53980.36910.054*
C210.3323 (2)0.5715 (2)0.50144 (19)0.0496 (7)
H210.34340.49740.50820.060*
C220.3262 (3)0.6553 (2)0.57389 (18)0.0522 (7)
H220.33300.63870.63100.063*
C230.3104 (2)0.76358 (19)0.56407 (15)0.0415 (6)
H230.30610.82040.61460.050*
C240.5083 (2)0.89162 (16)0.19044 (14)0.0316 (5)
H24A0.49790.90810.13080.038*
H24B0.60120.92550.21700.038*
C250.5065 (2)0.76899 (17)0.18398 (14)0.0328 (5)
C260.6166 (2)0.70312 (17)0.19058 (15)0.0387 (6)
H260.71510.72500.19770.046*
C270.6233 (3)0.49812 (18)0.19414 (17)0.0509 (7)
H27A0.57700.46730.24100.061*
H27B0.72460.51630.21290.061*
C280.6142 (3)0.41098 (18)0.11141 (16)0.0466 (6)
H28A0.66230.44010.06440.056*
H28B0.51320.39200.09200.056*
C290.6850 (3)0.30673 (17)0.12757 (16)0.0422 (6)
H29A0.78680.32620.14420.051*
H29B0.64070.28170.17770.051*
C300.6733 (3)0.21180 (17)0.04916 (16)0.0454 (6)
H30A0.71850.23600.00090.054*
H30B0.57160.19210.03220.054*
C310.7439 (3)0.10941 (17)0.06794 (15)0.0427 (6)
H31A0.84590.12930.08390.051*
H31B0.70030.08700.11930.051*
C320.7317 (3)0.01086 (17)0.00845 (15)0.0430 (6)
H32A0.62990.00720.02600.052*
H32B0.77890.03220.05900.052*
C330.7970 (3)0.09223 (17)0.01205 (15)0.0430 (6)
H33A0.89740.07330.03300.052*
H33B0.74570.11670.06000.052*
C340.7915 (3)0.18720 (17)0.06687 (15)0.0429 (6)
H34A0.69120.20440.08830.051*
H34B0.84380.16240.11430.051*
C350.8535 (3)0.29282 (17)0.04934 (15)0.0455 (6)
H35A0.79370.32360.00770.055*
H35B0.94990.27450.02120.055*
C360.8626 (3)0.38058 (17)0.13207 (15)0.0397 (6)
H36A0.91950.34860.17430.048*
H36B0.76560.40010.15910.048*
C370.9285 (3)0.48615 (17)0.11688 (15)0.0396 (6)
H37A1.02270.46710.08580.048*
H37C0.86710.52290.07940.048*
C380.9452 (3)0.56462 (18)0.20306 (15)0.0432 (6)
H38C0.84970.59350.22870.052*
H38A0.99030.52300.24430.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0375 (10)0.0340 (8)0.0512 (10)0.0034 (7)0.0123 (8)0.0086 (7)
O20.0314 (9)0.0370 (8)0.0403 (9)0.0042 (7)0.0061 (7)0.0049 (7)
N10.0317 (10)0.0210 (8)0.0362 (11)0.0022 (7)0.0042 (8)0.0046 (7)
N20.0294 (10)0.0297 (9)0.0279 (10)0.0015 (7)0.0025 (8)0.0058 (7)
N30.0338 (12)0.0308 (11)0.0760 (16)0.0051 (9)0.0020 (10)0.0035 (10)
N40.0373 (13)0.0324 (11)0.0869 (17)0.0053 (9)0.0011 (11)0.0018 (10)
N50.0375 (12)0.0319 (10)0.0561 (13)0.0098 (9)0.0019 (10)0.0004 (9)
N60.0459 (13)0.0370 (12)0.0724 (16)0.0090 (10)0.0151 (11)0.0079 (11)
N70.0390 (13)0.0407 (12)0.0462 (13)0.0067 (10)0.0021 (10)0.0016 (10)
N80.0532 (15)0.0488 (13)0.0639 (15)0.0019 (11)0.0071 (11)0.0134 (11)
C10.0290 (12)0.0226 (10)0.0312 (12)0.0031 (8)0.0027 (9)0.0007 (8)
C20.0334 (13)0.0345 (12)0.0388 (13)0.0066 (10)0.0002 (10)0.0082 (10)
C30.0308 (14)0.0428 (13)0.0454 (15)0.0072 (10)0.0023 (11)0.0020 (11)
C40.0291 (13)0.0388 (13)0.0420 (14)0.0026 (10)0.0064 (10)0.0002 (10)
C50.0356 (14)0.0301 (11)0.0347 (13)0.0006 (9)0.0066 (10)0.0019 (9)
C60.0282 (12)0.0244 (10)0.0293 (12)0.0022 (8)0.0020 (9)0.0010 (8)
C70.0319 (13)0.0284 (11)0.0284 (12)0.0036 (9)0.0002 (9)0.0043 (9)
C80.0236 (11)0.0269 (10)0.0301 (12)0.0023 (8)0.0027 (9)0.0030 (9)
C90.0302 (13)0.0215 (10)0.0331 (12)0.0002 (8)0.0015 (10)0.0026 (9)
C100.0425 (14)0.0226 (10)0.0387 (13)0.0029 (9)0.0039 (10)0.0059 (9)
C110.0291 (12)0.0207 (10)0.0367 (13)0.0002 (8)0.0043 (9)0.0072 (9)
C120.0300 (13)0.0332 (12)0.0460 (15)0.0038 (9)0.0025 (11)0.0077 (10)
C130.0353 (14)0.0388 (13)0.0604 (18)0.0075 (10)0.0163 (12)0.0031 (12)
C140.0559 (17)0.0396 (13)0.0404 (15)0.0048 (12)0.0168 (13)0.0029 (11)
C150.0476 (16)0.0424 (13)0.0364 (14)0.0009 (11)0.0015 (11)0.0131 (11)
C160.0323 (13)0.0308 (11)0.0419 (14)0.0044 (9)0.0057 (10)0.0106 (10)
C170.0354 (13)0.0372 (12)0.0265 (12)0.0018 (9)0.0000 (9)0.0045 (9)
C180.0228 (12)0.0360 (12)0.0357 (13)0.0000 (9)0.0001 (9)0.0117 (10)
C190.0408 (14)0.0341 (12)0.0395 (14)0.0008 (10)0.0002 (11)0.0093 (10)
C200.0427 (15)0.0311 (12)0.0605 (17)0.0018 (10)0.0032 (12)0.0067 (11)
C210.0360 (15)0.0412 (14)0.078 (2)0.0028 (11)0.0024 (13)0.0271 (14)
C220.0406 (16)0.0661 (18)0.0603 (18)0.0024 (13)0.0007 (13)0.0395 (15)
C230.0370 (14)0.0509 (14)0.0382 (14)0.0025 (11)0.0023 (11)0.0128 (11)
C240.0283 (12)0.0338 (11)0.0325 (12)0.0041 (9)0.0039 (9)0.0046 (9)
C250.0307 (13)0.0334 (12)0.0330 (12)0.0048 (9)0.0039 (10)0.0018 (9)
C260.0319 (13)0.0351 (13)0.0467 (14)0.0046 (10)0.0015 (11)0.0016 (10)
C270.0567 (18)0.0363 (13)0.0586 (17)0.0159 (12)0.0042 (13)0.0041 (12)
C280.0526 (17)0.0350 (13)0.0517 (16)0.0109 (11)0.0081 (12)0.0042 (11)
C290.0463 (15)0.0317 (12)0.0494 (15)0.0081 (10)0.0062 (12)0.0075 (11)
C300.0521 (16)0.0359 (13)0.0498 (16)0.0127 (11)0.0081 (12)0.0085 (11)
C310.0536 (16)0.0342 (12)0.0422 (14)0.0107 (11)0.0082 (12)0.0084 (11)
C320.0515 (16)0.0370 (13)0.0417 (14)0.0115 (11)0.0071 (11)0.0074 (10)
C330.0567 (17)0.0371 (13)0.0372 (14)0.0157 (11)0.0109 (12)0.0069 (10)
C340.0496 (16)0.0363 (13)0.0430 (14)0.0116 (11)0.0051 (11)0.0053 (10)
C350.0618 (18)0.0374 (13)0.0383 (14)0.0141 (12)0.0077 (12)0.0058 (11)
C360.0437 (15)0.0357 (12)0.0395 (14)0.0092 (10)0.0010 (11)0.0055 (10)
C370.0441 (15)0.0353 (12)0.0379 (14)0.0073 (10)0.0031 (11)0.0032 (10)
C380.0453 (15)0.0370 (13)0.0462 (15)0.0101 (11)0.0056 (11)0.0030 (11)
Geometric parameters (Å, º) top
O1—C71.222 (2)C19—C201.389 (3)
O2—C91.228 (2)C19—H190.9500
N1—C71.371 (3)C20—C211.373 (3)
N1—C11.434 (3)C20—H200.9500
N1—C101.478 (2)C21—C221.379 (3)
N2—C91.373 (3)C21—H210.9500
N2—C61.424 (2)C22—C231.388 (3)
N2—C171.474 (2)C22—H220.9500
N3—N41.324 (2)C23—H230.9500
N3—C251.357 (3)C24—C251.495 (3)
N4—N51.340 (3)C24—H24A0.9900
N5—C261.342 (3)C24—H24B0.9900
N5—C271.471 (3)C25—C261.363 (3)
N6—N71.238 (3)C26—H260.9500
N6—C381.477 (3)C27—C281.505 (3)
N7—N81.135 (3)C27—H27A0.9900
C1—C21.393 (3)C27—H27B0.9900
C1—C61.397 (3)C28—C291.536 (3)
C2—C31.375 (3)C28—H28A0.9900
C2—H20.9500C28—H28B0.9900
C3—C41.385 (3)C29—C301.515 (3)
C3—H30.9500C29—H29A0.9900
C4—C51.385 (3)C29—H29B0.9900
C4—H40.9500C30—C311.528 (3)
C5—C61.395 (3)C30—H30A0.9900
C5—H50.9500C30—H30B0.9900
C7—C81.523 (3)C31—C321.523 (3)
C8—C91.521 (3)C31—H31A0.9900
C8—C241.527 (3)C31—H31B0.9900
C8—H81.0000C32—C331.523 (3)
C10—C111.503 (3)C32—H32A0.9900
C10—H10A0.9900C32—H32B0.9900
C10—H10B0.9900C33—C341.521 (3)
C11—C161.389 (3)C33—H33A0.9900
C11—C121.392 (3)C33—H33B0.9900
C12—C131.383 (3)C34—C351.521 (3)
C12—H120.9500C34—H34A0.9900
C13—C141.377 (3)C34—H34B0.9900
C13—H130.9500C35—C361.521 (3)
C14—C151.384 (3)C35—H35A0.9900
C14—H140.9500C35—H35B0.9900
C15—C161.379 (3)C36—C371.525 (3)
C15—H150.9500C36—H36A0.9900
C16—H160.9500C36—H36B0.9900
C17—C181.518 (3)C37—C381.513 (3)
C17—H17A0.9900C37—H37A0.9900
C17—H17B0.9900C37—H37C0.9900
C18—C191.387 (3)C38—H38C0.9900
C18—C231.387 (3)C38—H38A0.9900
C7—N1—C1123.00 (16)C18—C23—C22120.7 (2)
C7—N1—C10119.34 (17)C18—C23—H23119.7
C1—N1—C10117.65 (16)C22—C23—H23119.7
C9—N2—C6122.66 (17)C25—C24—C8111.90 (17)
C9—N2—C17118.05 (17)C25—C24—H24A109.2
C6—N2—C17119.26 (17)C8—C24—H24A109.2
N4—N3—C25109.03 (18)C25—C24—H24B109.2
N3—N4—N5106.74 (18)C8—C24—H24B109.2
N4—N5—C26110.86 (17)H24A—C24—H24B107.9
N4—N5—C27119.71 (19)N3—C25—C26107.91 (19)
C26—N5—C27129.2 (2)N3—C25—C24122.42 (18)
N7—N6—C38115.6 (2)C26—C25—C24129.6 (2)
N8—N7—N6172.0 (2)N5—C26—C25105.5 (2)
C2—C1—C6118.94 (19)N5—C26—H26127.3
C2—C1—N1118.89 (18)C25—C26—H26127.3
C6—C1—N1122.12 (18)N5—C27—C28113.9 (2)
C3—C2—C1121.4 (2)N5—C27—H27A108.8
C3—C2—H2119.3C28—C27—H27A108.8
C1—C2—H2119.3N5—C27—H27B108.8
C2—C3—C4119.8 (2)C28—C27—H27B108.8
C2—C3—H3120.1H27A—C27—H27B107.7
C4—C3—H3120.1C27—C28—C29110.2 (2)
C5—C4—C3119.8 (2)C27—C28—H28A109.6
C5—C4—H4120.1C29—C28—H28A109.6
C3—C4—H4120.1C27—C28—H28B109.6
C4—C5—C6120.7 (2)C29—C28—H28B109.6
C4—C5—H5119.7H28A—C28—H28B108.1
C6—C5—H5119.7C30—C29—C28113.9 (2)
C5—C6—C1119.40 (19)C30—C29—H29A108.8
C5—C6—N2119.14 (18)C28—C29—H29A108.8
C1—C6—N2121.43 (18)C30—C29—H29B108.8
O1—C7—N1123.06 (18)C28—C29—H29B108.8
O1—C7—C8122.69 (19)H29A—C29—H29B107.7
N1—C7—C8114.09 (17)C29—C30—C31112.4 (2)
C9—C8—C7103.72 (15)C29—C30—H30A109.1
C9—C8—C24111.59 (16)C31—C30—H30A109.1
C7—C8—C24112.98 (17)C29—C30—H30B109.1
C9—C8—H8109.5C31—C30—H30B109.1
C7—C8—H8109.5H30A—C30—H30B107.9
C24—C8—H8109.5C32—C31—C30114.22 (19)
O2—C9—N2121.56 (19)C32—C31—H31A108.7
O2—C9—C8122.38 (19)C30—C31—H31A108.7
N2—C9—C8116.06 (17)C32—C31—H31B108.7
N1—C10—C11111.42 (16)C30—C31—H31B108.7
N1—C10—H10A109.3H31A—C31—H31B107.6
C11—C10—H10A109.3C33—C32—C31113.88 (19)
N1—C10—H10B109.3C33—C32—H32A108.8
C11—C10—H10B109.3C31—C32—H32A108.8
H10A—C10—H10B108.0C33—C32—H32B108.8
C16—C11—C12118.1 (2)C31—C32—H32B108.8
C16—C11—C10120.15 (19)H32A—C32—H32B107.7
C12—C11—C10121.70 (19)C34—C33—C32112.85 (19)
C13—C12—C11120.9 (2)C34—C33—H33A109.0
C13—C12—H12119.6C32—C33—H33A109.0
C11—C12—H12119.6C34—C33—H33B109.0
C14—C13—C12120.0 (2)C32—C33—H33B109.0
C14—C13—H13120.0H33A—C33—H33B107.8
C12—C13—H13120.0C35—C34—C33114.86 (19)
C13—C14—C15120.0 (2)C35—C34—H34A108.6
C13—C14—H14120.0C33—C34—H34A108.6
C15—C14—H14120.0C35—C34—H34B108.6
C16—C15—C14119.7 (2)C33—C34—H34B108.6
C16—C15—H15120.1H34A—C34—H34B107.5
C14—C15—H15120.1C34—C35—C36113.11 (19)
C15—C16—C11121.2 (2)C34—C35—H35A109.0
C15—C16—H16119.4C36—C35—H35A109.0
C11—C16—H16119.4C34—C35—H35B109.0
N2—C17—C18115.03 (17)C36—C35—H35B109.0
N2—C17—H17A108.5H35A—C35—H35B107.8
C18—C17—H17A108.5C35—C36—C37114.29 (18)
N2—C17—H17B108.5C35—C36—H36A108.7
C18—C17—H17B108.5C37—C36—H36A108.7
H17A—C17—H17B107.5C35—C36—H36B108.7
C19—C18—C23118.4 (2)C37—C36—H36B108.7
C19—C18—C17123.59 (19)H36A—C36—H36B107.6
C23—C18—C17117.94 (19)C38—C37—C36110.81 (18)
C18—C19—C20120.3 (2)C38—C37—H37A109.5
C18—C19—H19119.9C36—C37—H37A109.5
C20—C19—H19119.9C38—C37—H37C109.5
C21—C20—C19121.1 (2)C36—C37—H37C109.5
C21—C20—H20119.5H37A—C37—H37C108.1
C19—C20—H20119.5N6—C38—C37113.33 (19)
C20—C21—C22118.9 (2)N6—C38—H38C108.9
C20—C21—H21120.6C37—C38—H38C108.9
C22—C21—H21120.6N6—C38—H38A108.9
C21—C22—C23120.6 (2)C37—C38—H38A108.9
C21—C22—H22119.7H38C—C38—H38A107.7
C23—C22—H22119.7
C25—N3—N4—N50.1 (3)C10—C11—C12—C13179.42 (19)
N3—N4—N5—C260.2 (3)C11—C12—C13—C140.1 (3)
N3—N4—N5—C27175.6 (2)C12—C13—C14—C150.4 (3)
C7—N1—C1—C2128.6 (2)C13—C14—C15—C160.0 (3)
C10—N1—C1—C250.0 (2)C14—C15—C16—C110.6 (3)
C7—N1—C1—C653.9 (3)C12—C11—C16—C150.8 (3)
C10—N1—C1—C6127.5 (2)C10—C11—C16—C15179.04 (19)
C6—C1—C2—C31.1 (3)C9—N2—C17—C1872.5 (2)
N1—C1—C2—C3176.48 (19)C6—N2—C17—C18109.0 (2)
C1—C2—C3—C40.1 (3)N2—C17—C18—C190.5 (3)
C2—C3—C4—C50.8 (3)N2—C17—C18—C23178.86 (18)
C3—C4—C5—C60.8 (3)C23—C18—C19—C201.1 (3)
C4—C5—C6—C10.2 (3)C17—C18—C19—C20177.3 (2)
C4—C5—C6—N2178.23 (18)C18—C19—C20—C210.8 (3)
C2—C1—C6—C51.1 (3)C19—C20—C21—C220.2 (4)
N1—C1—C6—C5176.37 (18)C20—C21—C22—C230.2 (4)
C2—C1—C6—N2179.11 (18)C19—C18—C23—C220.8 (3)
N1—C1—C6—N21.6 (3)C17—C18—C23—C22177.7 (2)
C9—N2—C6—C5138.91 (19)C21—C22—C23—C180.1 (4)
C17—N2—C6—C542.7 (2)C9—C8—C24—C2561.4 (2)
C9—N2—C6—C143.1 (3)C7—C8—C24—C25177.80 (17)
C17—N2—C6—C1135.30 (19)N4—N3—C25—C260.3 (3)
C1—N1—C7—O1174.29 (19)N4—N3—C25—C24176.8 (2)
C10—N1—C7—O14.3 (3)C8—C24—C25—N339.0 (3)
C1—N1—C7—C810.3 (3)C8—C24—C25—C26136.7 (2)
C10—N1—C7—C8171.12 (17)N4—N5—C26—C250.4 (3)
O1—C7—C8—C9105.9 (2)C27—N5—C26—C25175.3 (2)
N1—C7—C8—C969.6 (2)N3—C25—C26—N50.4 (2)
O1—C7—C8—C2415.1 (3)C24—C25—C26—N5176.6 (2)
N1—C7—C8—C24169.45 (17)N4—N5—C27—C2870.5 (3)
C6—N2—C9—O2174.76 (17)C26—N5—C27—C28115.0 (3)
C17—N2—C9—O23.7 (3)N5—C27—C28—C29179.3 (2)
C6—N2—C9—C84.2 (3)C27—C28—C29—C30176.6 (2)
C17—N2—C9—C8177.39 (16)C28—C29—C30—C31179.6 (2)
C7—C8—C9—O299.5 (2)C29—C30—C31—C32178.6 (2)
C24—C8—C9—O222.4 (3)C30—C31—C32—C33177.6 (2)
C7—C8—C9—N279.4 (2)C31—C32—C33—C34176.5 (2)
C24—C8—C9—N2158.65 (16)C32—C33—C34—C35179.1 (2)
C7—N1—C10—C11129.1 (2)C33—C34—C35—C36172.9 (2)
C1—N1—C10—C1152.3 (2)C34—C35—C36—C37178.2 (2)
N1—C10—C11—C1664.5 (2)C35—C36—C37—C38175.1 (2)
N1—C10—C11—C12115.7 (2)N7—N6—C38—C3778.5 (3)
C16—C11—C12—C130.5 (3)C36—C37—C38—N6169.6 (2)

Experimental details

Crystal data
Chemical formulaC38H46N8O2
Mr646.83
Crystal system, space groupTriclinic, P1
Temperature (K)193
a, b, c (Å)9.4269 (2), 12.3304 (3), 15.5500 (4)
α, β, γ (°)101.121 (2), 92.175 (2), 92.935 (2)
V3)1769.11 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.20 × 0.06
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
33681, 8126, 4315
Rint0.076
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.147, 1.00
No. of reflections8126
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

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