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ISSN: 2414-3146

(4Z)-1-Do­decyl-4-(2-oxo­propyl­­idene)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

CROSSMARK_Color_square_no_text.svg

aHeterocyclic Organic Chemistry Laboratory URAC 21, Faculty of Sciences, Mohammed V University in Rabat, Av Ibn Battouta, BP 1014 Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: sebhaoui.jihad@gmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 12 October 2016; accepted 23 October 2016; online 1 November 2016)

In the title compound, C24H36N2O2, the orientation of the 2-oxo­propyl­idene substituent is determined by the formation of an intra­molecular N—H⋯O hydrogen bond. The benzodiazepine seven-membered ring adopts a slightly twisted boat conformation. The mol­ecules pack in a bilayer fashion with the dodecyl chains inter­calated to form the inner portion, and the benzodiazepine moieties on the outer surfaces.

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

Structure description

1,5-Benzodiazepine derivatives are an important class of heterocyclic compounds with versatile biological actions. They are used as anti­convulsivants, myorelaxants (Rudolph et al., 1999[Rudolph, U., Crestani, F., Benke, D., Brünig, I., Benson, J. A., Fritschy, J.-M., Martin, J. R., Bluethmann, H. & Möhler, H. (1999). Nature, 401, 796-800.]), anxiolytics, hypnotics and sedatives (Zellou et al., 1999[Zellou, A., Keita, A., Cherrah, Y., Essassi, E. M. & Hassar, M. (1999). Therapie, 54, 645-649.]). The commercial applications of these compounds as dyes for acrylic fibres and in photography have also been reported (Mauget-Fa et al., 2001[Mauget-Fa, M., Quaranta, M., Francoz, N. & BenEzra, D. (2001). Graefes Arch. Clin. Exp. Ophthalmol. 239, 501-508.]; Bishop et al., 2007[Bishop, S. C., Lerch, M. & McCord, B. R. (2007). J. Chromatogr. A, 1154, 481-484.]). Two published works indicate that 2,3,4,5-tetra­hydro-1H-1,5-benzodiazepine derivatives carrying carboxamide substituents are potentially important as therapeutic and prophylactic agents for diabetes, diabetic nephropathy, or glomerulosclerosis (Finch et al., 1996[Finch, H., Shah, P. & Carr, R. A. E. (1996). US Patent 5585376 A.]; Ohtake et al., 2007[Ohtake, Y., Fukaya, Y., Mihara, Y., Oishi, T., Takashima, Y., Shoji, T. & Morizono, D. (2007). EP Patent 1820799 A1.]).

In the title mol­ecule, the seven-membered ring adopts a slightly twisted boat conformation. An analysis of the conformation (Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) yielded the puckering parameters q2 = 0.893 (2), q3 = 0.255 (2) Å, φ2 = 18.2 (1) and φ3 = 130.0°. The overall puckering amplitude is 0.916 (2) Å. The dodecyl chain is oriented approximately over the bicyclic portion (Fig. 1[link]), while the orientation of the 2-oxo­propyl­idene substituent is determined by the intra­molecular hydrogen bond N1—H1⋯O2 (Table 1[link] and Fig. 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2 0.88 (2) 1.94 (2) 2.637 (2) 136 (2)
C5—H5⋯O1i 0.98 (2) 2.54 (2) 3.500 (2) 165.6 (17)
C2—H2⋯O2ii 0.97 (2) 2.48 (3) 3.276 (2) 139.4 (19)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z.
[Figure 1]
Figure 1
The title mol­ecule with labelling scheme and 50% probability ellipsoids. The intra­molecular N—H⋯O hydrogen bond is shown as a dotted line.

In the crystal, the dodecyl chains inter­calate to form the hydro­phobic portion of a bilayer, with the more polar bicyclic portions forming the outer faces (Fig. 2[link]). Weak C5—H5⋯O1i and C2—H2⋯O2ii [symmetry codes: (i) x, y − 1, z; (ii) x − 1, y + 1, z] hydrogen bonds help in establishing the surfaces of the bilayer (Table 1[link] and Fig. 3[link]).

[Figure 2]
Figure 2
Packing viewed along the b axis showing the inter­calation of the alkyl chains.
[Figure 3]
Figure 3
Detail of the inter­molecular C—H⋯O hydrogen bonding [symmetry codes: (i) x, y − 1, z; (ii) x − 1, y + 1, z].

Synthesis and crystallization

A mixture of (4Z)-2-oxo­propyl­idene-1,5-benzodiazepin-2-one (0.01 mol), K2CO3 (0.02 mol), dodecane bromide (0.02 mol) and tetra-n-butyl­ammonium bromide (0.001 mol) in di­methyl­formamide (60 ml) was stirred at room temperature for 48 h. The solution was filtered by suction filtration. The solvent was removed under reduced pressure. The residue was chromatographed on a silica-gel column using a mixture of hexane and ethyl acetate (80:20 v/v) as eluent, to afford the title compound as colourless crystals.

Refinement

Crystal and refinement details are presented in Table 2[link]. All H atoms were found in difference maps and refined with free coordinates and Uiso parameters.

Table 2
Experimental details

Crystal data
Chemical formula C24H36N2O2
Mr 384.55
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 150
a, b, c (Å) 8.2589 (9), 8.3715 (9), 18.097 (2)
α, β, γ (°) 87.327 (6), 82.242 (6), 63.248 (7)
V3) 1106.9 (2)
Z 2
Radiation type Cu Kα
μ (mm−1) 0.57
Crystal size (mm) 0.16 × 0.11 × 0.06
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan SADABS (Bruker, 2016[Bruker (2016). APEX3, SAINT, SADABS and SHELXTL, Bruker AXS, Inc., Madison, WI.])
Tmin, Tmax 0.84, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections 8388, 4075, 3242
Rint 0.037
(sin θ/λ)max−1) 0.615
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.138, 1.07
No. of reflections 4075
No. of parameters 397
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.17, −0.27
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT, SADABS and SHELXTL, Bruker AXS, Inc., Madison, WI.]), 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 (Bruker, 2016[Bruker (2016). APEX3, SAINT, SADABS and SHELXTL, Bruker AXS, Inc., Madison, WI.]).

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 (Bruker, 2016).

(4Z)-1-Dodecyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top
Crystal data top
C24H36N2O2Z = 2
Mr = 384.55F(000) = 420
Triclinic, P1Dx = 1.154 Mg m3
a = 8.2589 (9) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.3715 (9) ÅCell parameters from 5933 reflections
c = 18.097 (2) Åθ = 2.5–71.6°
α = 87.327 (6)°µ = 0.57 mm1
β = 82.242 (6)°T = 150 K
γ = 63.248 (7)°Block, colourless
V = 1106.9 (2) Å30.16 × 0.11 × 0.06 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
4075 independent reflections
Radiation source: INCOATEC IµS micro-focus source3242 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.037
Detector resolution: 10.4167 pixels mm-1θmax = 71.6°, θmin = 4.9°
ω scansh = 1010
Absorption correction: multi-scan
SADABS (Bruker, 2016)
k = 1010
Tmin = 0.84, Tmax = 0.96l = 2022
8388 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)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.138All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0635P)2 + 0.2871P]
where P = (Fo2 + 2Fc2)/3
4075 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49804 (17)0.95715 (16)0.11351 (8)0.0363 (3)
O20.85523 (18)0.18662 (16)0.11278 (8)0.0419 (3)
N10.5318 (2)0.46760 (19)0.12365 (8)0.0279 (3)
H10.600 (3)0.356 (3)0.1351 (13)0.052 (7)*
N20.30375 (19)0.84404 (17)0.16331 (8)0.0260 (3)
C10.2303 (2)0.7192 (2)0.16034 (9)0.0265 (4)
C20.0418 (2)0.7796 (2)0.17719 (10)0.0328 (4)
H20.037 (3)0.906 (3)0.1849 (14)0.055 (7)*
C30.0324 (3)0.6602 (3)0.18364 (11)0.0378 (4)
H30.166 (3)0.700 (3)0.1962 (11)0.032 (5)*
C40.0812 (3)0.4774 (3)0.17338 (10)0.0350 (4)
H40.025 (3)0.395 (3)0.1791 (12)0.044 (6)*
C50.2664 (3)0.4168 (2)0.15358 (10)0.0310 (4)
H50.352 (3)0.291 (3)0.1420 (12)0.039 (5)*
C60.3426 (2)0.5368 (2)0.14575 (9)0.0261 (3)
C70.6123 (2)0.5373 (2)0.06987 (9)0.0255 (3)
H70.844 (3)0.493 (3)0.0001 (11)0.032 (5)*
C80.4925 (2)0.7223 (2)0.04494 (9)0.0260 (4)
H8A0.380 (3)0.723 (3)0.0262 (11)0.037 (5)*
H8B0.556 (3)0.759 (3)0.0042 (11)0.033 (5)*
C90.4323 (2)0.8528 (2)0.10986 (9)0.0259 (4)
C100.7909 (2)0.4437 (2)0.04016 (10)0.0277 (4)
C110.9060 (2)0.2644 (2)0.06113 (10)0.0315 (4)
C121.0942 (3)0.1678 (3)0.01860 (13)0.0393 (5)
H12A1.181 (4)0.172 (3)0.0470 (14)0.059 (7)*
H12B1.116 (3)0.228 (3)0.0302 (15)0.058 (7)*
H12C1.119 (4)0.050 (4)0.0081 (18)0.087 (10)*
C130.2425 (3)0.9605 (2)0.23012 (10)0.0315 (4)
H13A0.103 (3)1.037 (3)0.2358 (12)0.046 (6)*
H13B0.305 (3)1.039 (3)0.2213 (11)0.038 (5)*
C140.2929 (2)0.8527 (2)0.30084 (10)0.0319 (4)
H14A0.228 (3)0.780 (3)0.3095 (12)0.041 (6)*
H14B0.251 (3)0.935 (3)0.3452 (13)0.051 (6)*
C150.4971 (2)0.7328 (2)0.30015 (10)0.0317 (4)
H15A0.544 (3)0.640 (3)0.2587 (12)0.037 (5)*
H15B0.563 (3)0.812 (3)0.2879 (12)0.040 (5)*
C160.5431 (3)0.6367 (3)0.37373 (10)0.0336 (4)
H16A0.472 (3)0.571 (3)0.3864 (12)0.043 (6)*
H16B0.498 (3)0.731 (3)0.4173 (14)0.052 (6)*
C170.7447 (3)0.5139 (2)0.37574 (10)0.0340 (4)
H17A0.791 (3)0.417 (3)0.3350 (14)0.052 (6)*
H17B0.816 (3)0.585 (3)0.3631 (12)0.042 (6)*
C180.7845 (3)0.4253 (3)0.45129 (10)0.0346 (4)
H18A0.707 (3)0.359 (3)0.4649 (13)0.051 (6)*
H18B0.737 (3)0.520 (3)0.4902 (13)0.047 (6)*
C190.9837 (3)0.3002 (2)0.45673 (10)0.0343 (4)
H19A1.029 (3)0.202 (3)0.4173 (13)0.044 (6)*
H19B1.058 (3)0.369 (3)0.4447 (13)0.048 (6)*
C201.0145 (3)0.2144 (2)0.53318 (10)0.0343 (4)
H20A0.939 (3)0.147 (3)0.5437 (13)0.049 (6)*
H20B0.967 (3)0.312 (3)0.5731 (13)0.043 (6)*
C211.2120 (3)0.0869 (2)0.54133 (10)0.0338 (4)
H21A1.259 (3)0.011 (3)0.5017 (13)0.046 (6)*
H21B1.287 (3)0.154 (3)0.5297 (12)0.042 (6)*
C221.2391 (3)0.0029 (3)0.61809 (11)0.0357 (4)
H22A1.159 (3)0.059 (3)0.6320 (13)0.052 (6)*
H22B1.193 (3)0.099 (3)0.6567 (13)0.048 (6)*
C231.4358 (3)0.1263 (3)0.62625 (12)0.0401 (4)
H23A1.516 (4)0.063 (3)0.6143 (14)0.058 (7)*
H23B1.479 (3)0.219 (3)0.5888 (14)0.050 (6)*
C241.4624 (4)0.2082 (3)0.70285 (14)0.0550 (6)
H24A1.600 (4)0.300 (4)0.7042 (16)0.077 (9)*
H24B1.426 (4)0.117 (4)0.7445 (16)0.066 (8)*
H24C1.388 (4)0.273 (4)0.7164 (17)0.082 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0366 (7)0.0284 (6)0.0495 (8)0.0200 (6)0.0030 (6)0.0033 (5)
O20.0400 (8)0.0286 (7)0.0529 (9)0.0124 (6)0.0063 (6)0.0098 (6)
N10.0302 (7)0.0216 (7)0.0320 (8)0.0118 (6)0.0044 (6)0.0038 (6)
N20.0288 (7)0.0220 (7)0.0276 (7)0.0117 (6)0.0037 (5)0.0004 (5)
C10.0315 (9)0.0260 (8)0.0250 (8)0.0153 (7)0.0049 (6)0.0019 (6)
C20.0326 (9)0.0310 (9)0.0352 (10)0.0151 (8)0.0032 (7)0.0033 (7)
C30.0322 (10)0.0435 (11)0.0416 (10)0.0213 (9)0.0029 (8)0.0045 (8)
C40.0432 (10)0.0398 (10)0.0326 (9)0.0280 (9)0.0059 (7)0.0045 (8)
C50.0424 (10)0.0290 (9)0.0271 (9)0.0206 (8)0.0062 (7)0.0028 (7)
C60.0309 (8)0.0257 (8)0.0246 (8)0.0147 (7)0.0067 (6)0.0040 (6)
C70.0310 (8)0.0235 (8)0.0260 (8)0.0148 (7)0.0068 (6)0.0000 (6)
C80.0271 (8)0.0230 (8)0.0276 (8)0.0110 (7)0.0048 (6)0.0044 (6)
C90.0254 (8)0.0198 (8)0.0317 (9)0.0087 (7)0.0070 (6)0.0036 (6)
C100.0281 (8)0.0248 (8)0.0318 (9)0.0128 (7)0.0064 (7)0.0021 (7)
C110.0310 (9)0.0257 (8)0.0397 (10)0.0128 (7)0.0110 (7)0.0001 (7)
C120.0296 (10)0.0303 (10)0.0570 (13)0.0116 (8)0.0071 (9)0.0034 (9)
C130.0363 (10)0.0244 (8)0.0317 (9)0.0118 (8)0.0023 (7)0.0039 (7)
C140.0331 (9)0.0338 (9)0.0296 (9)0.0158 (8)0.0014 (7)0.0037 (7)
C150.0336 (9)0.0332 (9)0.0285 (9)0.0155 (8)0.0025 (7)0.0013 (7)
C160.0355 (10)0.0354 (9)0.0305 (9)0.0163 (8)0.0045 (7)0.0012 (8)
C170.0378 (10)0.0344 (9)0.0305 (9)0.0166 (9)0.0059 (7)0.0017 (8)
C180.0379 (10)0.0340 (10)0.0315 (10)0.0156 (8)0.0056 (7)0.0013 (8)
C190.0396 (10)0.0347 (10)0.0303 (9)0.0181 (9)0.0053 (7)0.0016 (8)
C200.0390 (10)0.0340 (10)0.0320 (10)0.0179 (9)0.0057 (7)0.0022 (8)
C210.0381 (10)0.0330 (9)0.0314 (9)0.0166 (8)0.0067 (7)0.0037 (8)
C220.0431 (11)0.0350 (10)0.0327 (10)0.0204 (9)0.0062 (8)0.0025 (8)
C230.0464 (11)0.0379 (10)0.0394 (11)0.0200 (9)0.0139 (9)0.0040 (9)
C240.0745 (17)0.0507 (13)0.0491 (14)0.0320 (13)0.0288 (12)0.0158 (11)
Geometric parameters (Å, º) top
O1—C91.2263 (19)C14—H14A0.97 (2)
O2—C111.247 (2)C14—H14B1.00 (2)
N1—C71.360 (2)C15—C161.525 (3)
N1—C61.405 (2)C15—H15A1.01 (2)
N1—H10.88 (2)C15—H15B1.03 (2)
N2—C91.362 (2)C16—C171.517 (3)
N2—C11.4309 (19)C16—H16A0.97 (2)
N2—C131.473 (2)C16—H16B1.05 (2)
C1—C21.396 (2)C17—C181.528 (3)
C1—C61.400 (2)C17—H17A1.02 (2)
C2—C31.382 (2)C17—H17B1.01 (2)
C2—H20.97 (2)C18—C191.515 (3)
C3—C41.394 (3)C18—H18A1.03 (3)
C3—H31.00 (2)C18—H18B0.99 (2)
C4—C51.376 (3)C19—C201.527 (3)
C4—H40.98 (2)C19—H19A1.01 (2)
C5—C61.399 (2)C19—H19B1.01 (2)
C5—H50.98 (2)C20—C211.518 (3)
C7—C101.365 (2)C20—H20A1.01 (2)
C7—C81.502 (2)C20—H20B1.02 (2)
C8—C91.515 (2)C21—C221.525 (3)
C8—H8A1.03 (2)C21—H21A1.01 (2)
C8—H8B0.96 (2)C21—H21B1.01 (2)
C10—C111.436 (2)C22—C231.516 (3)
C10—H70.97 (2)C22—H22A1.01 (2)
C11—C121.506 (3)C22—H22B0.99 (2)
C12—H12A0.95 (3)C23—C241.516 (3)
C12—H12B1.03 (3)C23—H23A1.02 (3)
C12—H12C0.94 (3)C23—H23B0.96 (2)
C13—C141.525 (3)C24—H24A1.05 (3)
C13—H13A1.03 (2)C24—H24B1.02 (3)
C13—H13B1.00 (2)C24—H24C0.99 (3)
C14—C151.524 (3)
C7—N1—C6125.16 (15)C14—C15—C16112.49 (15)
C7—N1—H1115.3 (16)C14—C15—H15A110.6 (12)
C6—N1—H1117.0 (16)C16—C15—H15A108.4 (12)
C9—N2—C1123.31 (14)C14—C15—H15B107.5 (12)
C9—N2—C13119.43 (13)C16—C15—H15B111.2 (12)
C1—N2—C13117.17 (13)H15A—C15—H15B106.5 (16)
C2—C1—C6119.07 (15)C17—C16—C15114.65 (15)
C2—C1—N2118.86 (15)C17—C16—H16A110.3 (13)
C6—C1—N2121.94 (15)C15—C16—H16A110.0 (14)
C3—C2—C1120.67 (17)C17—C16—H16B108.4 (13)
C3—C2—H2119.9 (15)C15—C16—H16B109.6 (13)
C1—C2—H2119.4 (15)H16A—C16—H16B103.3 (18)
C2—C3—C4120.01 (17)C16—C17—C18112.69 (15)
C2—C3—H3122.0 (11)C16—C17—H17A109.8 (14)
C4—C3—H3117.9 (11)C18—C17—H17A109.3 (14)
C5—C4—C3119.89 (16)C16—C17—H17B108.9 (13)
C5—C4—H4121.9 (13)C18—C17—H17B110.0 (13)
C3—C4—H4118.2 (13)H17A—C17—H17B105.9 (18)
C4—C5—C6120.54 (17)C19—C18—C17115.22 (15)
C4—C5—H5123.4 (12)C19—C18—H18A109.9 (13)
C6—C5—H5116.0 (12)C17—C18—H18A109.4 (13)
C5—C6—C1119.64 (16)C19—C18—H18B110.1 (14)
C5—C6—N1117.97 (15)C17—C18—H18B108.6 (14)
C1—C6—N1122.39 (14)H18A—C18—H18B103.0 (18)
N1—C7—C10121.79 (15)C18—C19—C20112.74 (15)
N1—C7—C8116.00 (14)C18—C19—H19A108.9 (13)
C10—C7—C8122.22 (15)C20—C19—H19A109.0 (13)
C7—C8—C9109.41 (14)C18—C19—H19B108.8 (13)
C7—C8—H8A109.1 (11)C20—C19—H19B110.5 (13)
C9—C8—H8A109.9 (11)H19A—C19—H19B106.7 (18)
C7—C8—H8B111.1 (12)C21—C20—C19114.78 (16)
C9—C8—H8B109.7 (12)C21—C20—H20A108.5 (13)
H8A—C8—H8B107.6 (17)C19—C20—H20A108.7 (13)
O1—C9—N2123.08 (15)C21—C20—H20B108.9 (13)
O1—C9—C8121.36 (15)C19—C20—H20B109.2 (12)
N2—C9—C8115.55 (13)H20A—C20—H20B106.5 (17)
C7—C10—C11123.18 (16)C20—C21—C22113.78 (16)
C7—C10—H7120.6 (12)C20—C21—H21A108.8 (13)
C11—C10—H7116.0 (12)C22—C21—H21A109.5 (13)
O2—C11—C10122.41 (16)C20—C21—H21B108.3 (12)
O2—C11—C12119.32 (17)C22—C21—H21B110.3 (12)
C10—C11—C12118.27 (17)H21A—C21—H21B105.8 (17)
C11—C12—H12A109.1 (15)C23—C22—C21113.99 (16)
C11—C12—H12B114.8 (14)C23—C22—H22A109.3 (14)
H12A—C12—H12B102 (2)C21—C22—H22A111.5 (14)
C11—C12—H12C109.9 (19)C23—C22—H22B109.1 (14)
H12A—C12—H12C112 (2)C21—C22—H22B109.3 (13)
H12B—C12—H12C109 (2)H22A—C22—H22B103.0 (18)
N2—C13—C14111.77 (14)C24—C23—C22113.8 (2)
N2—C13—H13A110.2 (12)C24—C23—H23A109.4 (15)
C14—C13—H13A108.4 (13)C22—C23—H23A109.5 (14)
N2—C13—H13B105.3 (12)C24—C23—H23B109.9 (14)
C14—C13—H13B110.9 (12)C22—C23—H23B108.4 (15)
H13A—C13—H13B110.3 (17)H23A—C23—H23B105.5 (19)
C15—C14—C13114.11 (15)C23—C24—H24A110.0 (16)
C15—C14—H14A108.9 (13)C23—C24—H24B113.5 (15)
C13—C14—H14A110.0 (13)H24A—C24—H24B108 (2)
C15—C14—H14B107.8 (14)C23—C24—H24C112.0 (18)
C13—C14—H14B110.0 (14)H24A—C24—H24C108 (2)
H14A—C14—H14B105.6 (18)H24B—C24—H24C106 (2)
C9—N2—C1—C2135.43 (17)C13—N2—C9—O11.8 (3)
C13—N2—C1—C248.1 (2)C1—N2—C9—C81.0 (2)
C9—N2—C1—C648.7 (2)C13—N2—C9—C8177.42 (14)
C13—N2—C1—C6127.77 (17)C7—C8—C9—O1105.68 (18)
C6—C1—C2—C33.7 (3)C7—C8—C9—N273.53 (18)
N2—C1—C2—C3172.29 (16)N1—C7—C10—C111.9 (3)
C1—C2—C3—C40.1 (3)C8—C7—C10—C11177.63 (15)
C2—C3—C4—C52.9 (3)C7—C10—C11—O26.3 (3)
C3—C4—C5—C61.9 (3)C7—C10—C11—C12173.45 (16)
C4—C5—C6—C11.9 (3)C9—N2—C13—C14115.69 (17)
C4—C5—C6—N1178.46 (16)C1—N2—C13—C1461.0 (2)
C2—C1—C6—C54.6 (2)N2—C13—C14—C1558.3 (2)
N2—C1—C6—C5171.20 (15)C13—C14—C15—C16176.23 (14)
C2—C1—C6—N1175.74 (16)C14—C15—C16—C17179.39 (15)
N2—C1—C6—N18.4 (2)C15—C16—C17—C18178.22 (15)
C7—N1—C6—C5133.69 (17)C16—C17—C18—C19179.72 (16)
C7—N1—C6—C146.7 (2)C17—C18—C19—C20179.42 (15)
C6—N1—C7—C10165.76 (15)C18—C19—C20—C21179.65 (15)
C6—N1—C7—C813.8 (2)C19—C20—C21—C22179.93 (15)
N1—C7—C8—C963.24 (18)C20—C21—C22—C23179.33 (16)
C10—C7—C8—C9117.19 (17)C21—C22—C23—C24179.49 (17)
C1—N2—C9—O1178.22 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.88 (2)1.94 (2)2.637 (2)136 (2)
C5—H5···O1i0.98 (2)2.54 (2)3.500 (2)165.6 (17)
C2—H2···O2ii0.97 (2)2.48 (3)3.276 (2)139.4 (19)
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z.
 

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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