organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

7,9-Dido­decyl-6-methyl-3H,7H,8H,9H,9aH-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8-one

CROSSMARK_Color_square_no_text.svg

aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, bMedicinal Chemistry Laboratory, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, 10170 Rabat, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: youness.chimie14@gmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 19 September 2016; accepted 7 October 2016; online 14 October 2016)

The title compound, C30H55N5O, forms a micellar structure in the crystal with the dodecyl chains inter­calating and the bicyclic cores forming dimers across centres of symmetry, via weak C—H⋯N hydrogen bonds, and slipped π-stacking inter­actions between the five-membered rings.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Triazolotriazepine derivatives have been used as potent inhibitors of bone resorption (Chikazu et al., 2000[Chikazu, D., Shindo, M., Iwasaka, T., Katagiri, M., Manabe, N., Takato, T., Nakamura, K. & Kawaguchi, H. (2000). J. Bone Miner. Res. 15, 674-682.]). They also exhibit anti­fungal activity (Gupta et al., 2011[Gupta, M., Paul, S. & Gupta, R. (2011). Eur. J. Med. Chem. 46, 631-635.]). In a continuation of our previous work on the preparation of new nitro­gen-bridged heterocycles, we report herein the crystal structure of the title compound obtained by alkyl­ation reaction under phase-transfer catalysis (Essassi et al., 1977[Essassi, E. M., Lavergne, J.-P. & Viallffont, Ph. (1977). Tetrahedron, 33, 2807-2812.]; Harmaoui et al., 2015[Harmaoui, A., Bouhfid, R., Essassi, E. M., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o1-o2.]; El Bakri et al., 2016a[El Bakri, Y., Harmaoui, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2016a). IUCrData, 1, x161229.],b[El Bakri, Y., Harmaoui, A., Sebhaoui, J., Ramli, Y., Essassi, E. M. & Mague, J. T. (2016b). IUCrData, 1, x161245.]).

The title compound (Fig. 1[link]) forms a micellar structure in the crystal, with the dodecyl chains inter­calating (Fig. 2[link]) and the bicyclic cores forming dimers across centres of symmetry, via C2—H2⋯N5(−x, −y, 1 − z) hydrogen bonds, and slipped π-stacking inter­actions between the five-membered rings of the same two mol­ecules (Table 1[link] and Fig. 3[link]). The distance between the centroids of the two rings is 3.572 (1) Å, while the separation between the planes of the two rings is 3.062 (1) Å. A puckering analysis of the seven-membered ring yielded the parameters q2 = 0.843 (1) Å, q3 = 0.243 (1) Å, φ2 = 30.07 (9)° and φ3 = 121.0 (3)°. The total puckering amplitude is 0.888 (1) Å, and the ring is bowl-shaped.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯N5i 0.985 (16) 2.544 (16) 3.4749 (18) 157.5 (12)
Symmetry code: (i) -x, -y, -z+1.
[Figure 1]
Figure 1
The title mol­ecule with labelling scheme and 50% probability ellipsoids.
[Figure 2]
Figure 2
Packing viewed along the a axis with inter­molecular C—H⋯N hydrogen bonds shown as dotted lines.
[Figure 3]
Figure 3
Detail of the pair-wise C—H⋯N hydrogen bonds and the π-stacking inter­action between mol­ecules related by the centre of symmetry at (0,0,1/2).

Synthesis and crystallization

To a solution of 6-methyl-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8(9H)-one (0.2 g, 1.21 mmol) in N,N-di­methyl­formamide (10 ml), was added potassium carbonate (0.16 g, 1.21 mmol), dodecane bromide (0.35 ml, 1.21 mmol) and a catalytic amount of tetra n-butyl­ammonium bromide. The reaction mixture was stirred for 12 h. The solution was then concentrated to dryness under reduced pressure, and the residue was extracted with di­chloro­methane. The precipitate formed under cooling was filtered and recrystallized from ethanol solution, to give crystals of the title compound with a yield of 60%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C30H55N5O
Mr 501.79
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 150
a, b, c (Å) 8.8895 (7), 8.9652 (7), 19.6555 (15)
α, β, γ (°) 95.093 (3), 95.922 (3), 98.563 (3)
V3) 1532.1 (2)
Z 2
Radiation type Cu Kα
μ (mm−1) 0.51
Crystal size (mm) 0.24 × 0.22 × 0.09
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.84, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections 11896, 5705, 4818
Rint 0.033
(sin θ/λ)max−1) 0.619
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.135, 1.06
No. of reflections 5705
No. of parameters 545
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.25, −0.24
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

7,9-Didodecyl-6-methyl-3H,7H,8H,9H,9aH-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8-one top
Crystal data top
C30H55N5OZ = 2
Mr = 501.79F(000) = 556
Triclinic, P1Dx = 1.088 Mg m3
a = 8.8895 (7) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.9652 (7) ÅCell parameters from 9089 reflections
c = 19.6555 (15) Åθ = 5.0–72.6°
α = 95.093 (3)°µ = 0.51 mm1
β = 95.922 (3)°T = 150 K
γ = 98.563 (3)°Plate, colourless
V = 1532.1 (2) Å30.24 × 0.22 × 0.09 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
5705 independent reflections
Radiation source: INCOATEC IµS micro-focus source4818 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.4167 pixels mm-1θmax = 72.6°, θmin = 5.0°
ω scansh = 910
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1110
Tmin = 0.84, Tmax = 0.95l = 2124
11896 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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.135All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0697P)2 + 0.2812P]
where P = (Fo2 + 2Fc2)/3
5705 reflections(Δ/σ)max = 0.002
545 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.24 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.45566 (11)0.27197 (11)0.49999 (5)0.0424 (3)
N10.02842 (13)0.34896 (12)0.41655 (6)0.0341 (3)
N20.01039 (13)0.19478 (12)0.42508 (6)0.0339 (3)
N30.24079 (13)0.12205 (12)0.44702 (6)0.0341 (3)
N40.14934 (14)0.03199 (13)0.40412 (6)0.0416 (3)
N50.00352 (14)0.04911 (13)0.42035 (6)0.0379 (3)
C10.31635 (15)0.24759 (15)0.48942 (7)0.0332 (3)
C20.21506 (15)0.35300 (14)0.51936 (7)0.0318 (3)
H20.1329 (18)0.2876 (18)0.5376 (8)0.034 (4)*
C30.13968 (15)0.42197 (14)0.45922 (7)0.0323 (3)
C40.08281 (15)0.08795 (14)0.43266 (7)0.0327 (3)
C50.15362 (17)0.11278 (16)0.40653 (8)0.0397 (3)
H50.244 (2)0.1628 (19)0.3975 (8)0.043 (4)*
C60.19538 (19)0.58068 (16)0.44484 (8)0.0398 (3)
H6A0.134 (2)0.609 (2)0.4066 (10)0.056 (5)*
H6B0.190 (2)0.652 (2)0.4837 (10)0.052 (5)*
H6C0.303 (2)0.592 (2)0.4360 (10)0.058 (5)*
C70.30173 (16)0.47174 (15)0.57624 (7)0.0349 (3)
H7A0.387 (2)0.537 (2)0.5580 (9)0.044 (4)*
H7B0.2302 (18)0.5415 (18)0.5891 (8)0.035 (4)*
C80.35884 (18)0.40684 (15)0.64135 (7)0.0367 (3)
H8A0.276 (2)0.334 (2)0.6556 (9)0.048 (5)*
H8B0.436 (2)0.341 (2)0.6285 (9)0.048 (5)*
C90.42445 (19)0.53097 (16)0.69965 (8)0.0417 (4)
H9A0.506 (2)0.608 (2)0.6840 (10)0.057 (5)*
H9B0.341 (2)0.589 (2)0.7127 (10)0.057 (5)*
C100.49422 (19)0.47228 (16)0.76379 (8)0.0405 (3)
H10A0.422 (2)0.392 (2)0.7769 (10)0.054 (5)*
H10B0.579 (2)0.421 (2)0.7539 (10)0.054 (5)*
C110.55100 (18)0.59269 (16)0.82448 (8)0.0411 (3)
H11A0.627 (2)0.678 (2)0.8093 (9)0.052 (5)*
H11B0.458 (2)0.638 (2)0.8377 (10)0.054 (5)*
C120.62686 (19)0.52907 (17)0.88617 (8)0.0410 (3)
H12A0.559 (2)0.441 (2)0.8985 (9)0.046 (5)*
H12B0.715 (2)0.482 (2)0.8725 (10)0.055 (5)*
C130.67791 (18)0.64442 (17)0.94923 (8)0.0395 (3)
H13A0.748 (2)0.736 (2)0.9361 (9)0.047 (5)*
H13B0.585 (2)0.686 (2)0.9639 (9)0.051 (5)*
C140.75696 (19)0.57803 (17)1.00942 (8)0.0405 (3)
H14A0.687 (2)0.490 (2)1.0206 (9)0.049 (5)*
H14B0.848 (2)0.536 (2)0.9943 (9)0.049 (5)*
C150.80604 (18)0.69082 (17)1.07346 (8)0.0393 (3)
H15A0.717 (2)0.731 (2)1.0884 (9)0.043 (4)*
H15B0.8740 (19)0.782 (2)1.0627 (8)0.041 (4)*
C160.88550 (19)0.62427 (18)1.13337 (8)0.0416 (3)
H16A0.977 (2)0.585 (2)1.1186 (10)0.053 (5)*
H16B0.820 (2)0.538 (2)1.1450 (10)0.052 (5)*
C170.93187 (19)0.73634 (18)1.19785 (8)0.0432 (4)
H17A0.840 (2)0.776 (2)1.2122 (10)0.054 (5)*
H17B0.999 (2)0.826 (2)1.1865 (9)0.047 (5)*
C181.0118 (2)0.6687 (2)1.25739 (9)0.0542 (4)
H18A0.946 (2)0.580 (3)1.2698 (11)0.063 (6)*
H18B1.110 (3)0.631 (3)1.2441 (11)0.069 (6)*
H18C1.038 (3)0.739 (3)1.2985 (12)0.078 (7)*
C190.33053 (18)0.01086 (16)0.41839 (7)0.0377 (3)
H19A0.269 (2)0.090 (2)0.4172 (9)0.047 (5)*
H19B0.423 (2)0.018 (2)0.4497 (10)0.053 (5)*
C200.36916 (18)0.04379 (16)0.34731 (8)0.0389 (3)
H20A0.425 (2)0.147 (2)0.3486 (10)0.058 (5)*
H20B0.275 (2)0.044 (2)0.3159 (9)0.051 (5)*
C210.46416 (16)0.06797 (16)0.31747 (7)0.0365 (3)
H21A0.4037 (18)0.1743 (19)0.3148 (8)0.036 (4)*
H21B0.558 (2)0.0686 (19)0.3493 (9)0.042 (4)*
C220.50409 (17)0.03997 (17)0.24531 (8)0.0392 (3)
H22A0.584 (2)0.106 (2)0.2336 (9)0.051 (5)*
H22B0.550 (2)0.066 (2)0.2436 (9)0.045 (4)*
C230.36489 (17)0.07753 (18)0.19116 (8)0.0398 (3)
H23A0.313 (2)0.182 (2)0.1939 (9)0.046 (5)*
H23B0.291 (2)0.007 (2)0.2020 (9)0.052 (5)*
C240.39822 (17)0.06601 (17)0.11712 (8)0.0392 (3)
H24A0.475 (2)0.136 (2)0.1071 (9)0.052 (5)*
H24B0.444 (2)0.039 (2)0.1127 (9)0.044 (4)*
C250.25471 (17)0.11520 (18)0.06640 (8)0.0396 (3)
H25A0.209 (2)0.218 (2)0.0731 (9)0.046 (5)*
H25B0.179 (2)0.048 (2)0.0759 (10)0.056 (5)*
C260.27837 (18)0.10872 (18)0.00890 (8)0.0401 (3)
H26A0.354 (2)0.178 (2)0.0212 (10)0.060 (5)*
H26B0.323 (2)0.002 (2)0.0143 (9)0.047 (5)*
C270.13099 (18)0.16044 (19)0.05681 (8)0.0410 (3)
H27A0.086 (2)0.264 (2)0.0495 (9)0.051 (5)*
H27B0.056 (2)0.093 (2)0.0457 (10)0.059 (5)*
C280.14696 (19)0.15499 (19)0.13293 (8)0.0441 (4)
H28A0.222 (2)0.224 (2)0.1459 (10)0.057 (5)*
H28B0.194 (2)0.049 (2)0.1405 (10)0.056 (5)*
C290.0032 (2)0.2072 (2)0.17858 (8)0.0499 (4)
H29A0.049 (2)0.312 (3)0.1713 (11)0.069 (6)*
H29B0.078 (3)0.138 (3)0.1629 (12)0.079 (7)*
C300.0099 (3)0.1989 (3)0.25445 (10)0.0656 (5)
H30A0.082 (3)0.266 (3)0.2704 (13)0.089 (8)*
H30B0.049 (3)0.092 (3)0.2641 (14)0.095 (8)*
H30C0.093 (3)0.240 (3)0.2837 (13)0.084 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0316 (6)0.0416 (6)0.0510 (6)0.0038 (4)0.0038 (4)0.0024 (4)
N10.0359 (6)0.0248 (5)0.0383 (6)0.0008 (4)0.0058 (5)0.0038 (4)
N20.0337 (6)0.0255 (5)0.0378 (6)0.0013 (4)0.0073 (4)0.0020 (4)
N30.0341 (6)0.0303 (6)0.0358 (6)0.0047 (4)0.0026 (4)0.0007 (4)
N40.0411 (7)0.0325 (6)0.0447 (7)0.0037 (5)0.0089 (5)0.0001 (5)
N50.0415 (7)0.0293 (6)0.0384 (6)0.0008 (5)0.0042 (5)0.0004 (5)
C10.0317 (7)0.0296 (6)0.0361 (7)0.0024 (5)0.0039 (5)0.0052 (5)
C20.0310 (7)0.0257 (6)0.0358 (7)0.0012 (5)0.0047 (5)0.0031 (5)
C30.0309 (7)0.0272 (6)0.0365 (7)0.0033 (5)0.0040 (5)0.0022 (5)
C40.0352 (7)0.0289 (6)0.0310 (6)0.0016 (5)0.0025 (5)0.0009 (5)
C50.0367 (8)0.0321 (7)0.0438 (8)0.0030 (5)0.0099 (6)0.0002 (6)
C60.0403 (9)0.0300 (7)0.0447 (8)0.0009 (6)0.0085 (6)0.0067 (6)
C70.0339 (7)0.0267 (6)0.0398 (7)0.0014 (5)0.0088 (6)0.0008 (5)
C80.0414 (8)0.0270 (6)0.0380 (7)0.0026 (6)0.0065 (6)0.0003 (5)
C90.0442 (9)0.0296 (7)0.0452 (8)0.0026 (6)0.0137 (6)0.0017 (6)
C100.0449 (9)0.0309 (7)0.0413 (8)0.0043 (6)0.0075 (6)0.0022 (6)
C110.0402 (8)0.0346 (7)0.0436 (8)0.0054 (6)0.0103 (6)0.0037 (6)
C120.0442 (9)0.0352 (7)0.0402 (8)0.0069 (6)0.0051 (6)0.0037 (6)
C130.0372 (8)0.0363 (7)0.0414 (8)0.0064 (6)0.0055 (6)0.0042 (6)
C140.0414 (8)0.0378 (8)0.0396 (8)0.0069 (6)0.0025 (6)0.0030 (6)
C150.0365 (8)0.0382 (8)0.0407 (8)0.0061 (6)0.0021 (6)0.0026 (6)
C160.0416 (9)0.0399 (8)0.0411 (8)0.0057 (6)0.0009 (6)0.0001 (6)
C170.0407 (9)0.0443 (8)0.0406 (8)0.0019 (6)0.0021 (6)0.0013 (6)
C180.0572 (11)0.0587 (11)0.0419 (9)0.0027 (9)0.0048 (8)0.0031 (8)
C190.0408 (8)0.0325 (7)0.0399 (7)0.0119 (6)0.0018 (6)0.0022 (5)
C200.0435 (8)0.0336 (7)0.0406 (7)0.0131 (6)0.0006 (6)0.0035 (6)
C210.0329 (7)0.0327 (7)0.0425 (7)0.0094 (5)0.0052 (6)0.0005 (5)
C220.0326 (8)0.0391 (8)0.0447 (8)0.0076 (6)0.0014 (6)0.0013 (6)
C230.0331 (8)0.0450 (8)0.0411 (8)0.0079 (6)0.0030 (6)0.0031 (6)
C240.0365 (8)0.0395 (8)0.0414 (8)0.0073 (6)0.0048 (6)0.0007 (6)
C250.0377 (8)0.0432 (8)0.0389 (7)0.0095 (6)0.0052 (6)0.0035 (6)
C260.0403 (8)0.0414 (8)0.0392 (8)0.0092 (6)0.0056 (6)0.0027 (6)
C270.0402 (8)0.0449 (8)0.0389 (8)0.0110 (6)0.0045 (6)0.0028 (6)
C280.0501 (9)0.0434 (8)0.0395 (8)0.0113 (7)0.0051 (6)0.0024 (6)
C290.0544 (10)0.0536 (10)0.0419 (8)0.0169 (8)0.0010 (7)0.0005 (7)
C300.0879 (16)0.0689 (13)0.0408 (9)0.0264 (12)0.0031 (9)0.0010 (8)
Geometric parameters (Å, º) top
O1—C11.2177 (17)C15—H15B0.993 (18)
N1—C31.2840 (17)C16—C171.526 (2)
N1—N21.4031 (15)C16—H16A0.99 (2)
N2—C41.3646 (17)C16—H16B0.96 (2)
N2—C51.3684 (17)C17—C181.525 (2)
N3—C11.3804 (16)C17—H17A0.99 (2)
N3—C41.3858 (18)C17—H17B0.981 (19)
N3—C191.4753 (18)C18—H18A0.98 (2)
N4—C51.3009 (19)C18—H18B1.03 (2)
N4—N51.3976 (18)C18—H18C0.97 (2)
N5—C41.3112 (17)C19—C201.516 (2)
C1—C21.5212 (19)C19—H19A0.982 (19)
C2—C31.5226 (17)C19—H19B0.968 (19)
C2—C71.5309 (17)C20—C211.5202 (19)
C2—H20.985 (16)C20—H20A0.98 (2)
C3—C61.4967 (18)C20—H20B0.989 (19)
C5—H50.985 (17)C21—C221.530 (2)
C6—H6A0.96 (2)C21—H21A1.016 (16)
C6—H6B0.96 (2)C21—H21B0.990 (17)
C6—H6C0.98 (2)C22—C231.522 (2)
C7—C81.5232 (19)C22—H22A1.021 (19)
C7—H7A1.003 (18)C22—H22B0.982 (18)
C7—H7B0.991 (17)C23—C241.524 (2)
C8—C91.5278 (18)C23—H23A0.989 (19)
C8—H8A0.986 (19)C23—H23B1.01 (2)
C8—H8B1.008 (18)C24—C251.519 (2)
C9—C101.518 (2)C24—H24A1.020 (19)
C9—H9A1.02 (2)C24—H24B0.988 (18)
C9—H9B1.01 (2)C25—C261.521 (2)
C10—C111.5257 (19)C25—H25A0.978 (19)
C10—H10A0.96 (2)C25—H25B0.99 (2)
C10—H10B0.96 (2)C26—C271.518 (2)
C11—C121.523 (2)C26—H26A1.01 (2)
C11—H11A1.03 (2)C26—H26B1.002 (19)
C11—H11B1.02 (2)C27—C281.522 (2)
C12—C131.5259 (19)C27—H27A0.988 (19)
C12—H12A0.987 (19)C27—H27B0.99 (2)
C12—H12B0.99 (2)C28—C291.516 (2)
C13—C141.525 (2)C28—H28A1.01 (2)
C13—H13A1.025 (19)C28—H28B1.01 (2)
C13—H13B1.02 (2)C29—C301.515 (3)
C14—C151.5254 (19)C29—H29A1.00 (2)
C14—H14A0.99 (2)C29—H29B1.03 (2)
C14—H14B1.01 (2)C30—H30A1.00 (3)
C15—C161.523 (2)C30—H30B1.01 (3)
C15—H15A0.980 (19)C30—H30C1.03 (3)
C3—N1—N2115.03 (11)C17—C16—H16A109.8 (11)
C4—N2—C5104.47 (11)C15—C16—H16B109.9 (11)
C4—N2—N1129.11 (11)C17—C16—H16B108.4 (11)
C5—N2—N1123.86 (11)H16A—C16—H16B105.7 (16)
C1—N3—C4123.85 (12)C18—C17—C16113.25 (14)
C1—N3—C19119.05 (11)C18—C17—H17A110.1 (11)
C4—N3—C19116.98 (11)C16—C17—H17A109.5 (11)
C5—N4—N5107.30 (11)C18—C17—H17B109.8 (10)
C4—N5—N4106.66 (11)C16—C17—H17B109.1 (10)
O1—C1—N3120.92 (13)H17A—C17—H17B104.8 (15)
O1—C1—C2123.27 (12)C17—C18—H18A110.8 (12)
N3—C1—C2115.79 (11)C17—C18—H18B111.2 (12)
C1—C2—C3106.74 (11)H18A—C18—H18B106.4 (17)
C1—C2—C7113.06 (11)C17—C18—H18C112.9 (14)
C3—C2—C7113.32 (10)H18A—C18—H18C106.9 (19)
C1—C2—H2106.2 (9)H18B—C18—H18C108.4 (18)
C3—C2—H2106.8 (9)N3—C19—C20111.16 (11)
C7—C2—H2110.2 (9)N3—C19—H19A107.4 (10)
N1—C3—C6115.35 (12)C20—C19—H19A111.3 (10)
N1—C3—C2123.32 (11)N3—C19—H19B107.0 (11)
C6—C3—C2121.31 (11)C20—C19—H19B110.3 (11)
N5—C4—N2110.79 (12)H19A—C19—H19B109.4 (15)
N5—C4—N3125.37 (12)C19—C20—C21111.94 (12)
N2—C4—N3123.71 (11)C19—C20—H20A110.7 (11)
N4—C5—N2110.77 (13)C21—C20—H20A109.0 (11)
N4—C5—H5127.7 (10)C19—C20—H20B110.6 (11)
N2—C5—H5121.5 (10)C21—C20—H20B110.3 (11)
C3—C6—H6A111.4 (11)H20A—C20—H20B103.9 (15)
C3—C6—H6B110.8 (11)C20—C21—C22113.66 (12)
H6A—C6—H6B106.8 (16)C20—C21—H21A108.5 (9)
C3—C6—H6C110.5 (11)C22—C21—H21A108.0 (9)
H6A—C6—H6C109.9 (16)C20—C21—H21B110.2 (10)
H6B—C6—H6C107.3 (16)C22—C21—H21B110.8 (10)
C8—C7—C2114.45 (11)H21A—C21—H21B105.3 (13)
C8—C7—H7A111.5 (10)C23—C22—C21112.44 (12)
C2—C7—H7A110.5 (10)C23—C22—H22A109.6 (10)
C8—C7—H7B107.4 (9)C21—C22—H22A107.8 (10)
C2—C7—H7B107.5 (9)C23—C22—H22B108.1 (10)
H7A—C7—H7B105.0 (13)C21—C22—H22B111.3 (10)
C7—C8—C9112.14 (11)H22A—C22—H22B107.5 (14)
C7—C8—H8A110.3 (10)C22—C23—C24115.38 (13)
C9—C8—H8A111.2 (11)C22—C23—H23A109.4 (10)
C7—C8—H8B107.1 (10)C24—C23—H23A107.6 (10)
C9—C8—H8B112.5 (10)C22—C23—H23B108.3 (11)
H8A—C8—H8B103.2 (14)C24—C23—H23B108.4 (11)
C10—C9—C8114.01 (12)H23A—C23—H23B107.6 (14)
C10—C9—H9A107.9 (11)C25—C24—C23111.74 (12)
C8—C9—H9A110.8 (11)C25—C24—H24A108.6 (10)
C10—C9—H9B108.4 (11)C23—C24—H24A107.7 (10)
C8—C9—H9B109.4 (11)C25—C24—H24B111.0 (10)
H9A—C9—H9B106.1 (16)C23—C24—H24B108.8 (10)
C9—C10—C11115.08 (12)H24A—C24—H24B109.0 (14)
C9—C10—H10A109.2 (11)C24—C25—C26115.11 (13)
C11—C10—H10A110.7 (12)C24—C25—H25A109.3 (10)
C9—C10—H10B110.8 (11)C26—C25—H25A109.2 (10)
C11—C10—H10B107.8 (12)C24—C25—H25B109.2 (11)
H10A—C10—H10B102.6 (16)C26—C25—H25B106.4 (11)
C12—C11—C10112.89 (12)H25A—C25—H25B107.4 (15)
C12—C11—H11A109.5 (10)C27—C26—C25112.44 (13)
C10—C11—H11A109.6 (10)C27—C26—H26A107.9 (11)
C12—C11—H11B110.0 (11)C25—C26—H26A109.1 (11)
C10—C11—H11B107.1 (11)C27—C26—H26B111.3 (10)
H11A—C11—H11B107.7 (15)C25—C26—H26B107.3 (10)
C11—C12—C13114.47 (12)H26A—C26—H26B108.7 (15)
C11—C12—H12A110.3 (10)C26—C27—C28114.92 (13)
C13—C12—H12A110.1 (10)C26—C27—H27A110.5 (10)
C11—C12—H12B109.4 (11)C28—C27—H27A108.8 (11)
C13—C12—H12B110.2 (11)C26—C27—H27B108.8 (11)
H12A—C12—H12B101.7 (15)C28—C27—H27B106.4 (11)
C14—C13—C12113.11 (12)H27A—C27—H27B107.2 (15)
C14—C13—H13A110.3 (10)C29—C28—C27112.92 (14)
C12—C13—H13A109.7 (10)C29—C28—H28A108.3 (11)
C14—C13—H13B109.5 (10)C27—C28—H28A108.1 (11)
C12—C13—H13B108.6 (11)C29—C28—H28B111.5 (11)
H13A—C13—H13B105.3 (15)C27—C28—H28B108.9 (11)
C13—C14—C15113.90 (13)H28A—C28—H28B106.8 (15)
C13—C14—H14A108.4 (11)C30—C29—C28113.61 (17)
C15—C14—H14A109.7 (11)C30—C29—H29A109.4 (12)
C13—C14—H14B109.1 (10)C28—C29—H29A111.7 (12)
C15—C14—H14B110.1 (11)C30—C29—H29B109.6 (13)
H14A—C14—H14B105.3 (15)C28—C29—H29B106.6 (13)
C16—C15—C14113.75 (13)H29A—C29—H29B105.6 (18)
C16—C15—H15A108.9 (10)C29—C30—H30A110.3 (14)
C14—C15—H15A109.7 (10)C29—C30—H30B111.4 (15)
C16—C15—H15B109.2 (10)H30A—C30—H30B108 (2)
C14—C15—H15B110.7 (10)C29—C30—H30C111.0 (14)
H15A—C15—H15B104.1 (14)H30A—C30—H30C105 (2)
C15—C16—C17113.71 (13)H30B—C30—H30C111 (2)
C15—C16—H16A109.0 (11)
C3—N1—N2—C448.18 (19)N5—N4—C5—N21.22 (17)
C3—N1—N2—C5152.86 (14)C4—N2—C5—N41.05 (16)
C5—N4—N5—C40.89 (16)N1—N2—C5—N4164.34 (12)
C4—N3—C1—O1179.78 (12)C1—C2—C7—C866.68 (17)
C19—N3—C1—O14.44 (19)C3—C2—C7—C8171.69 (12)
C4—N3—C1—C21.58 (19)C2—C7—C8—C9172.05 (13)
C19—N3—C1—C2177.36 (11)C7—C8—C9—C10175.44 (14)
O1—C1—C2—C3112.27 (14)C8—C9—C10—C11176.11 (14)
N3—C1—C2—C365.88 (14)C9—C10—C11—C12177.18 (14)
O1—C1—C2—C712.99 (19)C10—C11—C12—C13177.03 (14)
N3—C1—C2—C7168.86 (11)C11—C12—C13—C14178.55 (14)
N2—N1—C3—C6172.28 (12)C12—C13—C14—C15178.85 (14)
N2—N1—C3—C25.9 (2)C13—C14—C15—C16179.78 (14)
C1—C2—C3—N175.46 (16)C14—C15—C16—C17178.91 (14)
C7—C2—C3—N1159.43 (14)C15—C16—C17—C18179.79 (14)
C1—C2—C3—C6102.59 (15)C1—N3—C19—C2094.60 (15)
C7—C2—C3—C622.51 (19)C4—N3—C19—C2089.34 (15)
N4—N5—C4—N20.24 (15)N3—C19—C20—C21178.96 (11)
N4—N5—C4—N3176.25 (12)C19—C20—C21—C22179.29 (12)
C5—N2—C4—N50.46 (16)C20—C21—C22—C2369.87 (16)
N1—N2—C4—N5162.53 (12)C21—C22—C23—C24174.73 (12)
C5—N2—C4—N3175.63 (13)C22—C23—C24—C25176.29 (13)
N1—N2—C4—N313.6 (2)C23—C24—C25—C26179.37 (13)
C1—N3—C4—N5148.14 (14)C24—C25—C26—C27179.54 (13)
C19—N3—C4—N527.72 (19)C25—C26—C27—C28179.41 (13)
C1—N3—C4—N236.3 (2)C26—C27—C28—C29179.83 (13)
C19—N3—C4—N2147.79 (13)C27—C28—C29—C30178.61 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N5i0.985 (16)2.544 (16)3.4749 (18)157.5 (12)
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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