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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Ethyl 5-oxo-4-phenyl-5,6-di­hydro-4H-1,3,4-oxadiazine-2-carboxyl­ate

aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: kbu68umesha@rediffmail.com

(Received 7 May 2014; accepted 14 May 2014; online 17 May 2014)

The asymmetric unit of title compound, C12H12N2O4, consists of two independent mol­ecules. In each mol­ecule, the oxadiazine ring has a flattened envelope conformation with the methyl­ene C atom as the flap atom, and the eth­oxy­carbonyl unit is in a syn-periplanar conformation with respect to the oxadiazine ring as indicated by O—C—C=O torsion angles of 1.9 (4) and 2.5 (4)°. The dihedral angles between the mean plane of the oxadiazine ring and the phenyl ring are 80.07 (13) and 42.98 (14)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and stacked in a double-column along the a-axis direction.

Related literature

For the biological activity of oxadiazine derivatives, see: Barbari et al. (2003[Barbari, M., Kraljevi, S., Grce, M. & Zorc, B. (2003). Acta Pharm. 53, 175-186.]); Gsell & Maientisch (1998[Gsell, L. & Maientisch, P. (1998). WO Patent 9806710.]). For a related structure, see: Chopra et al. (2004[Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2413-o2414.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O4

  • Mr = 248.24

  • Triclinic, [P \overline 1]

  • a = 9.3499 (7) Å

  • b = 9.3601 (8) Å

  • c = 15.2707 (15) Å

  • α = 104.007 (8)°

  • β = 99.366 (7)°

  • γ = 107.862 (7)°

  • V = 1192.9 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 9756 measured reflections

  • 4176 independent reflections

  • 2173 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.177

  • S = 1.03

  • 4176 reflections

  • 327 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2A—H2A2⋯O1Ai 0.97 2.55 3.150 (3) 120
C14B—H14A⋯O3Aii 0.97 2.59 3.418 (4) 143
C14B—H14B⋯O5Bii 0.97 2.57 3.163 (3) 120
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Heterocyclic compounds containing nitrogen and oxygen atoms are of great synthetic interest due to their versatile biological significance. Oxadiazine derivatives are one among those heterocyclic compounds exhibiting various biological activities, for instance 1,2,5-oxadiazine-3,6-diones are potent antiviral agents (Barbari et al., 2003). Also, as an important type of insecticides, oxadiazine derivatives are highly efficient and of low toxicity (Gsell & Maientisch, 1998). With this background on oxadiazine derivatives, we have synthesized the title compound to study its crystal structure.

The two independent molecules (A and B) of the title compound (Fig. 1) in the asymmetric unit exhibit highly planar conformation, with their maximum deviations on ring planes at N1A and N3B are 0.081 (2) Å and 0.055 (2) Å, respectively. The central oxadiazine moiety adopts a flattened envelope conformation with puckering parameters Q(2) = 0.281 (3) Å, Q(3) = 0.118 (3) Å and ϕ = 325.4 (6)° (Cremer & Pople, 1975). The bond lengths and angles are generally within normal ranges and are comparable to a related structure (Chopra et al., 2004). In the molecules A and B, the oxadiazine moiety makes a dihedral angle of 80.07 (13) and 42.98 (14)°, with the phenyl rings (C4A–C9A and C16B–C21B), respectively. The ethoxycarbonyl unit is in a syn-periplanar conformation with respect to the oxadiazine moiety, as indicated by the torsion angles of 1.9 (4)° (O1A—C1A—C10A—O3A) and 2.5 (4)° (O5B—C13B—C22B—O7B) for A and B, respectively. The crystal structure is stabilized by C—H···O hydrogen bonds and the molecules are stacked in a column along the a axis (Fig. 2).

Related literature top

For the biological activity of oxadiazine derivatives, see: Barbari et al. (2003); Gsell & Maientisch (1998). For a related structure, see: Chopra et al. (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Ethyl 5-oxo-4-phenyl-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxylate were obtained from ethyl 2-oxo-2-(2-phenylhydrazinyl) acetate by one pot condensation-cyclization reaction with chloroacetylchloride using potassium carbonate in dry acetone as a solvent. Compounds were purified by column chromatography using petroleum ether and acetone in (2:8) as eluent.

Refinement top

H atoms were placed at idealized positions and allowed to ride on their parent atoms with C—H distances in the range of 0.93 to 0.97 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective diagram of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the b axis.
Ethyl 5-oxo-4-phenyl-5,6-dihydro-4H-1,3,4-oxadiazine- 2-carboxylate top
Crystal data top
C12H12N2O4Z = 4
Mr = 248.24F(000) = 520
Triclinic, P1Dx = 1.382 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3499 (7) ÅCell parameters from 4176 reflections
b = 9.3601 (8) Åθ = 2.4–25.0°
c = 15.2707 (15) ŵ = 0.11 mm1
α = 104.007 (8)°T = 296 K
β = 99.366 (7)°Block, colourless
γ = 107.862 (7)°0.30 × 0.25 × 0.20 mm
V = 1192.9 (2) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.034
ω and ϕ scansθmax = 25.0°, θmin = 2.4°
9756 measured reflectionsh = 1111
4176 independent reflectionsk = 1111
2173 reflections with I > 2σ(I)l = 1818
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0687P)2 + 0.0133P]
where P = (Fo2 + 2Fc2)/3
4176 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C12H12N2O4γ = 107.862 (7)°
Mr = 248.24V = 1192.9 (2) Å3
Triclinic, P1Z = 4
a = 9.3499 (7) ÅMo Kα radiation
b = 9.3601 (8) ŵ = 0.11 mm1
c = 15.2707 (15) ÅT = 296 K
α = 104.007 (8)°0.30 × 0.25 × 0.20 mm
β = 99.366 (7)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2173 reflections with I > 2σ(I)
9756 measured reflectionsRint = 0.034
4176 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.177H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å3
4176 reflectionsΔρmin = 0.20 e Å3
327 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1A0.9018 (3)0.5053 (2)0.41230 (12)0.0818 (9)
O2A0.9228 (3)0.1798 (2)0.24645 (13)0.0852 (9)
O3A0.8395 (2)0.7645 (2)0.47867 (12)0.0751 (8)
O4A0.7043 (2)0.7358 (2)0.33599 (11)0.0627 (7)
N1A0.8228 (2)0.3648 (2)0.22576 (13)0.0497 (7)
N2A0.7753 (2)0.4882 (2)0.26292 (14)0.0496 (8)
C1A0.8179 (3)0.5490 (3)0.35128 (17)0.0523 (9)
C2A0.8926 (4)0.3456 (3)0.38006 (18)0.0762 (13)
C3A0.8834 (3)0.2883 (3)0.27857 (18)0.0590 (10)
C4A0.7924 (3)0.3134 (3)0.12527 (16)0.0431 (8)
C5A0.6417 (3)0.2277 (3)0.07184 (16)0.0523 (9)
C6A0.6136 (3)0.1792 (3)0.02421 (17)0.0590 (10)
C7A0.7342 (3)0.2172 (3)0.06527 (17)0.0583 (10)
C8A0.8838 (3)0.3026 (3)0.01176 (17)0.0586 (10)
C9A0.9132 (3)0.3525 (3)0.08430 (17)0.0540 (9)
C10A0.7883 (3)0.6949 (3)0.39674 (18)0.0538 (9)
C11A0.6807 (3)0.8841 (3)0.37234 (19)0.0649 (11)
C12A0.5841 (4)0.9068 (3)0.2930 (2)0.0778 (12)
O5B0.4012 (2)0.5021 (2)0.41180 (12)0.0781 (8)
O6B0.4292 (2)0.1793 (2)0.24830 (12)0.0734 (8)
O7B0.3404 (2)0.7627 (2)0.47626 (12)0.0757 (8)
O8B0.2062 (2)0.7323 (2)0.33296 (11)0.0615 (7)
N3B0.3194 (2)0.3572 (2)0.22398 (13)0.0472 (7)
N4B0.2769 (2)0.4843 (2)0.26183 (13)0.0474 (7)
C13B0.3189 (3)0.5460 (3)0.34960 (16)0.0483 (9)
C14B0.3933 (4)0.3432 (3)0.37963 (18)0.0704 (11)
C15B0.3850 (3)0.2857 (3)0.27812 (17)0.0536 (9)
C16B0.2910 (3)0.3093 (3)0.12345 (15)0.0423 (8)
C17B0.3345 (3)0.4229 (3)0.08030 (17)0.0526 (9)
C18B0.3045 (3)0.3784 (4)0.01600 (18)0.0618 (11)
C19B0.2330 (3)0.2206 (3)0.06714 (17)0.0590 (10)
C20B0.1896 (3)0.1073 (3)0.02371 (18)0.0611 (10)
C21B0.2172 (3)0.1515 (3)0.07198 (17)0.0546 (9)
C22B0.2899 (3)0.6925 (3)0.39472 (17)0.0522 (9)
C23B0.1793 (3)0.8789 (3)0.36856 (19)0.0650 (11)
C24B0.0808 (3)0.8990 (3)0.2889 (2)0.0775 (12)
H2A10.801600.278200.392600.0920*
H2A20.983300.335800.415300.0920*
H5A0.560500.203000.100200.0630*
H6A0.512900.120800.061100.0710*
H7A0.714500.184800.130000.0700*
H8A0.964900.326700.040200.0700*
H9A1.013800.412100.121000.0650*
H11A0.779900.971300.397300.0780*
H11B0.628100.879000.421900.0780*
H12A0.640500.919200.246500.1170*
H12B0.559900.999500.315200.1170*
H12C0.489500.816400.266300.1170*
H14A0.302400.275200.391900.0850*
H14B0.484200.334100.415200.0850*
H17B0.383800.528800.115600.0630*
H18B0.332100.454200.046100.0740*
H19B0.213900.190400.131900.0710*
H20B0.141800.001300.058900.0730*
H21B0.186500.075800.101800.0660*
H23A0.277400.967600.393300.0780*
H23B0.126800.873000.418100.0780*
H24A0.136500.911100.242000.1160*
H24B0.055500.991100.310500.1160*
H24C0.013100.807700.262700.1160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.1398 (19)0.0665 (13)0.0441 (12)0.0626 (14)0.0008 (11)0.0092 (10)
O2A0.149 (2)0.0725 (14)0.0581 (13)0.0775 (15)0.0200 (12)0.0185 (11)
O3A0.1091 (16)0.0733 (14)0.0425 (12)0.0502 (13)0.0084 (10)0.0023 (10)
O4A0.0855 (13)0.0551 (12)0.0523 (11)0.0435 (11)0.0094 (9)0.0070 (9)
N1A0.0726 (14)0.0467 (12)0.0389 (12)0.0355 (11)0.0130 (10)0.0119 (10)
N2A0.0628 (13)0.0466 (13)0.0433 (13)0.0308 (11)0.0118 (10)0.0078 (10)
C1A0.0688 (17)0.0472 (16)0.0420 (16)0.0269 (14)0.0091 (12)0.0114 (13)
C2A0.130 (3)0.0616 (19)0.0494 (18)0.0566 (19)0.0152 (16)0.0158 (15)
C3A0.089 (2)0.0500 (17)0.0475 (17)0.0387 (16)0.0135 (14)0.0171 (14)
C4A0.0540 (15)0.0418 (14)0.0389 (14)0.0270 (12)0.0097 (11)0.0109 (11)
C5A0.0491 (15)0.0557 (17)0.0525 (16)0.0221 (13)0.0155 (12)0.0116 (13)
C6A0.0495 (16)0.0674 (18)0.0533 (17)0.0251 (14)0.0037 (13)0.0080 (14)
C7A0.077 (2)0.0672 (19)0.0397 (15)0.0435 (16)0.0124 (14)0.0117 (14)
C8A0.0625 (17)0.0724 (19)0.0577 (18)0.0366 (15)0.0271 (14)0.0264 (15)
C9A0.0483 (15)0.0568 (17)0.0581 (17)0.0235 (13)0.0114 (12)0.0156 (14)
C10A0.0669 (17)0.0499 (16)0.0464 (16)0.0282 (14)0.0140 (13)0.0096 (13)
C11A0.0750 (19)0.0528 (17)0.0652 (19)0.0331 (15)0.0164 (15)0.0033 (14)
C12A0.098 (2)0.078 (2)0.077 (2)0.0574 (19)0.0208 (17)0.0264 (18)
O5B0.1242 (17)0.0720 (14)0.0437 (11)0.0611 (13)0.0019 (10)0.0102 (10)
O6B0.1116 (16)0.0736 (14)0.0603 (13)0.0652 (13)0.0217 (11)0.0245 (11)
O7B0.1060 (16)0.0771 (14)0.0410 (11)0.0505 (13)0.0045 (10)0.0002 (10)
O8B0.0810 (13)0.0600 (12)0.0489 (11)0.0438 (11)0.0083 (9)0.0084 (9)
N3B0.0641 (13)0.0467 (12)0.0399 (12)0.0330 (11)0.0126 (10)0.0134 (10)
N4B0.0577 (13)0.0451 (12)0.0418 (12)0.0283 (11)0.0086 (9)0.0077 (10)
C13B0.0578 (16)0.0470 (15)0.0394 (15)0.0233 (13)0.0056 (12)0.0110 (12)
C14B0.111 (2)0.0634 (19)0.0514 (17)0.0511 (18)0.0157 (15)0.0216 (15)
C15B0.0681 (17)0.0512 (16)0.0485 (16)0.0303 (14)0.0134 (13)0.0176 (14)
C16B0.0453 (14)0.0443 (15)0.0402 (14)0.0239 (12)0.0109 (11)0.0083 (12)
C17B0.0541 (15)0.0503 (16)0.0542 (17)0.0209 (13)0.0102 (12)0.0174 (14)
C18B0.0666 (18)0.081 (2)0.0532 (17)0.0378 (17)0.0191 (14)0.0312 (16)
C19B0.0553 (17)0.083 (2)0.0397 (15)0.0378 (16)0.0083 (12)0.0067 (16)
C20B0.0577 (17)0.0594 (18)0.0550 (18)0.0253 (15)0.0054 (13)0.0013 (15)
C21B0.0563 (16)0.0498 (16)0.0551 (17)0.0231 (14)0.0108 (12)0.0089 (14)
C22B0.0593 (16)0.0550 (17)0.0440 (16)0.0280 (14)0.0106 (12)0.0105 (13)
C23B0.078 (2)0.0525 (17)0.0672 (19)0.0377 (15)0.0175 (15)0.0060 (14)
C24B0.098 (2)0.078 (2)0.084 (2)0.0613 (19)0.0261 (18)0.0335 (18)
Geometric parameters (Å, º) top
O1A—C1A1.340 (3)C5A—H5A0.9300
O1A—C2A1.427 (4)C6A—H6A0.9300
O2A—C3A1.206 (4)C7A—H7A0.9300
O3A—C10A1.199 (3)C8A—H8A0.9300
O4A—C10A1.320 (3)C9A—H9A0.9300
O4A—C11A1.462 (3)C11A—H11B0.9700
O5B—C13B1.345 (3)C11A—H11A0.9700
O5B—C14B1.423 (3)C12A—H12A0.9600
O6B—C15B1.210 (3)C12A—H12B0.9600
O7B—C22B1.195 (3)C12A—H12C0.9600
O8B—C22B1.323 (3)C13B—C22B1.503 (4)
O8B—C23B1.462 (3)C14B—C15B1.493 (4)
N1A—C4A1.444 (3)C16B—C17B1.375 (4)
N1A—C3A1.365 (3)C16B—C21B1.383 (4)
N1A—N2A1.390 (3)C17B—C18B1.383 (4)
N2A—C1A1.272 (3)C18B—C19B1.380 (4)
N3B—N4B1.393 (3)C19B—C20B1.376 (4)
N3B—C16B1.446 (3)C20B—C21B1.376 (4)
N3B—C15B1.365 (3)C23B—C24B1.489 (4)
N4B—C13B1.265 (3)C14B—H14A0.9700
C1A—C10A1.503 (4)C14B—H14B0.9700
C2A—C3A1.491 (4)C17B—H17B0.9300
C4A—C5A1.382 (4)C18B—H18B0.9300
C4A—C9A1.374 (4)C19B—H19B0.9300
C5A—C6A1.380 (3)C20B—H20B0.9300
C6A—C7A1.372 (4)C21B—H21B0.9300
C7A—C8A1.374 (4)C23B—H23A0.9700
C8A—C9A1.380 (3)C23B—H23B0.9700
C11A—C12A1.488 (4)C24B—H24A0.9600
C2A—H2A10.9700C24B—H24B0.9600
C2A—H2A20.9700C24B—H24C0.9600
O1A···O3A2.669 (3)C10A···H23Bix3.0100
O1A···N1A2.701 (3)C15B···H21B2.8500
O1A···O1Ai3.032 (3)C16B···H5A3.0200
O1A···C2Ai3.150 (3)C16B···H9Avi3.0300
O2A···C9A3.272 (3)C18B···H8Avi3.0100
O3A···C14Bii3.418 (4)C19B···H6A3.0300
O3A···O1A2.669 (3)C19B···H8Avi3.0200
O4A···N2A2.644 (3)C21B···H5A3.0400
O5B···N3B2.724 (3)C22B···H11B3.0100
O5B···O7B2.667 (3)C24B···H19Bx3.0800
O5B···O5Bii3.024 (3)H2A1···O7Bii2.6200
O5B···C14Bii3.163 (3)H2A2···O3Ai2.6600
O6B···C21B2.976 (3)H2A2···O1Ai2.5500
O7B···O5B2.667 (3)H5A···O6B2.7700
O8B···N4B2.638 (3)H5A···C16B3.0200
O1A···H2A2i2.5500H5A···C21B3.0400
O2A···H24Biii2.7200H6A···C5Aiv3.0900
O2A···H20Biv2.8100H6A···C19B3.0300
O3A···H2A2i2.6600H7A···H12Cviii2.5800
O3A···H11B2.6500H7A···H24Aviii2.5400
O3A···H11A2.6800H8A···C18Bix3.0100
O3A···H14Aii2.5900H8A···C19Bix3.0200
O5B···H14Bii2.5700H9A···N4Bix2.7700
O6B···H12Bv2.6600H9A···C16Bix3.0300
O6B···H5A2.7700H11A···O3A2.6800
O6B···H21B2.6500H11B···C22B3.0100
O7B···H11B2.9100H11B···O3A2.6500
O7B···H23A2.6900H11B···O7B2.9100
O7B···H2A1ii2.6200H12A···H19Bviii2.5900
O7B···H14Bii2.6500H12B···O6Bxi2.6600
O7B···H23B2.6400H12C···H7Aviii2.5800
N1A···O1A2.701 (3)H14A···O3Aii2.5900
N2A···O4A2.644 (3)H14B···O5Bii2.5700
N3B···O5B2.724 (3)H14B···O7Bii2.6500
N4B···O8B2.638 (3)H17B···N4B2.6600
N4B···H17B2.6600H18B···C5Aviii3.0400
N4B···H9Avi2.7700H19B···C24Bx3.0800
C2A···O1Ai3.150 (3)H19B···H12Aviii2.5900
C7A···C21Biv3.596 (4)H19B···H24Cx2.5200
C8A···C8Avii3.562 (4)H20B···O2Aiv2.8100
C9A···O2A3.272 (3)H21B···O6B2.6500
C14B···O3Aii3.418 (4)H21B···C15B2.8500
C14B···O5Bii3.163 (3)H21B···C7Aiv3.0000
C18B···C18Bviii3.544 (5)H23A···O7B2.6900
C21B···O6B2.976 (3)H23B···O7B2.6400
C21B···C7Aiv3.596 (4)H23B···C10Avi3.0100
C5A···H6Aiv3.0900H24A···H7Aviii2.5400
C5A···H18Bviii3.0400H24B···O2Axii2.7200
C7A···H21Biv3.0000H24C···H19Bx2.5200
C1A—O1A—C2A114.7 (2)H12B—C12A—H12C109.00
C10A—O4A—C11A116.1 (2)C11A—C12A—H12A110.00
C13B—O5B—C14B114.6 (2)C11A—C12A—H12B109.00
C22B—O8B—C23B116.02 (19)C11A—C12A—H12C109.00
C3A—N1A—C4A121.4 (2)H12A—C12A—H12B109.00
N2A—N1A—C3A123.2 (2)H12A—C12A—H12C110.00
N2A—N1A—C4A115.21 (19)O5B—C13B—N4B127.0 (2)
N1A—N2A—C1A116.5 (2)O5B—C13B—C22B112.3 (2)
N4B—N3B—C16B114.74 (19)N4B—C13B—C22B120.5 (2)
C15B—N3B—C16B122.9 (2)O5B—C14B—C15B114.3 (2)
N4B—N3B—C15B122.32 (19)O6B—C15B—N3B124.3 (2)
N3B—N4B—C13B117.6 (2)O6B—C15B—C14B120.6 (2)
O1A—C1A—N2A126.9 (3)N3B—C15B—C14B115.0 (2)
O1A—C1A—C10A112.7 (2)N3B—C16B—C17B119.1 (2)
N2A—C1A—C10A120.1 (2)N3B—C16B—C21B119.9 (2)
O1A—C2A—C3A114.0 (2)C17B—C16B—C21B121.0 (2)
N1A—C3A—C2A114.7 (2)C16B—C17B—C18B119.4 (3)
O2A—C3A—C2A121.8 (3)C17B—C18B—C19B119.5 (3)
O2A—C3A—N1A123.5 (2)C18B—C19B—C20B120.9 (2)
C5A—C4A—C9A121.1 (2)C19B—C20B—C21B119.7 (3)
N1A—C4A—C5A119.4 (2)C16B—C21B—C20B119.5 (2)
N1A—C4A—C9A119.5 (2)O7B—C22B—O8B125.9 (3)
C4A—C5A—C6A119.0 (3)O7B—C22B—C13B122.5 (2)
C5A—C6A—C7A120.0 (3)O8B—C22B—C13B111.6 (2)
C6A—C7A—C8A120.7 (2)O8B—C23B—C24B107.2 (2)
C7A—C8A—C9A119.8 (3)O5B—C14B—H14A109.00
C4A—C9A—C8A119.4 (3)O5B—C14B—H14B109.00
O3A—C10A—O4A125.7 (3)C15B—C14B—H14A109.00
O3A—C10A—C1A122.2 (3)C15B—C14B—H14B109.00
O4A—C10A—C1A112.1 (2)H14A—C14B—H14B108.00
O4A—C11A—C12A107.0 (2)C16B—C17B—H17B120.00
C3A—C2A—H2A1109.00C18B—C17B—H17B120.00
C3A—C2A—H2A2109.00C17B—C18B—H18B120.00
O1A—C2A—H2A2109.00C19B—C18B—H18B120.00
O1A—C2A—H2A1109.00C18B—C19B—H19B120.00
H2A1—C2A—H2A2108.00C20B—C19B—H19B120.00
C6A—C5A—H5A121.00C19B—C20B—H20B120.00
C4A—C5A—H5A120.00C21B—C20B—H20B120.00
C5A—C6A—H6A120.00C16B—C21B—H21B120.00
C7A—C6A—H6A120.00C20B—C21B—H21B120.00
C8A—C7A—H7A120.00O8B—C23B—H23A110.00
C6A—C7A—H7A120.00O8B—C23B—H23B110.00
C9A—C8A—H8A120.00C24B—C23B—H23A110.00
C7A—C8A—H8A120.00C24B—C23B—H23B110.00
C4A—C9A—H9A120.00H23A—C23B—H23B109.00
C8A—C9A—H9A120.00C23B—C24B—H24A109.00
C12A—C11A—H11A110.00C23B—C24B—H24B110.00
C12A—C11A—H11B110.00C23B—C24B—H24C109.00
O4A—C11A—H11A110.00H24A—C24B—H24B109.00
O4A—C11A—H11B110.00H24A—C24B—H24C109.00
H11A—C11A—H11B109.00H24B—C24B—H24C110.00
C2A—O1A—C1A—N2A24.5 (4)N4B—N3B—C15B—O6B176.9 (2)
C2A—O1A—C1A—C10A161.4 (3)C15B—N3B—C16B—C21B48.9 (4)
C1A—O1A—C2A—C3A36.4 (4)N3B—N4B—C13B—O5B0.1 (4)
C11A—O4A—C10A—O3A3.7 (4)N3B—N4B—C13B—C22B174.4 (2)
C11A—O4A—C10A—C1A174.9 (2)N2A—C1A—C10A—O3A172.7 (3)
C10A—O4A—C11A—C12A180.0 (3)N2A—C1A—C10A—O4A6.0 (4)
C13B—O5B—C14B—C15B35.2 (4)O1A—C1A—C10A—O4A179.4 (2)
C14B—O5B—C13B—N4B22.8 (4)O1A—C1A—C10A—O3A1.9 (4)
C14B—O5B—C13B—C22B162.3 (2)O1A—C2A—C3A—O2A156.5 (3)
C22B—O8B—C23B—C24B178.7 (2)O1A—C2A—C3A—N1A25.5 (4)
C23B—O8B—C22B—C13B176.4 (2)N1A—C4A—C5A—C6A179.9 (2)
C23B—O8B—C22B—O7B2.4 (4)C5A—C4A—C9A—C8A1.3 (4)
N2A—N1A—C3A—O2A179.0 (3)C9A—C4A—C5A—C6A0.9 (4)
N2A—N1A—C3A—C2A1.0 (4)N1A—C4A—C9A—C8A179.7 (2)
C4A—N1A—N2A—C1A171.4 (2)C4A—C5A—C6A—C7A0.5 (4)
C3A—N1A—C4A—C9A78.9 (3)C5A—C6A—C7A—C8A0.4 (4)
N2A—N1A—C4A—C5A73.3 (3)C6A—C7A—C8A—C9A0.8 (4)
C4A—N1A—C3A—O2A4.0 (4)C7A—C8A—C9A—C4A1.2 (4)
C4A—N1A—C3A—C2A174.0 (2)O5B—C13B—C22B—O7B2.5 (4)
C3A—N1A—N2A—C1A13.3 (3)O5B—C13B—C22B—O8B178.7 (2)
N2A—N1A—C4A—C9A105.7 (3)N4B—C13B—C22B—O7B172.8 (3)
C3A—N1A—C4A—C5A102.1 (3)N4B—C13B—C22B—O8B6.0 (4)
N1A—N2A—C1A—O1A1.0 (4)O5B—C14B—C15B—O6B155.0 (3)
N1A—N2A—C1A—C10A172.8 (2)O5B—C14B—C15B—N3B27.5 (4)
C15B—N3B—N4B—C13B8.9 (3)N3B—C16B—C17B—C18B178.5 (3)
C16B—N3B—N4B—C13B170.1 (2)C21B—C16B—C17B—C18B0.3 (5)
N4B—N3B—C15B—C14B5.8 (4)N3B—C16B—C21B—C20B179.5 (3)
C16B—N3B—C15B—O6B2.0 (4)C17B—C16B—C21B—C20B1.3 (5)
C16B—N3B—C15B—C14B175.3 (2)C16B—C17B—C18B—C19B0.7 (5)
N4B—N3B—C16B—C17B46.1 (3)C17B—C18B—C19B—C20B0.8 (5)
N4B—N3B—C16B—C21B132.1 (3)C18B—C19B—C20B—C21B0.2 (5)
C15B—N3B—C16B—C17B132.8 (3)C19B—C20B—C21B—C16B1.2 (4)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y1, z; (iv) x+1, y, z; (v) x, y1, z; (vi) x1, y, z; (vii) x+2, y+1, z; (viii) x+1, y+1, z; (ix) x+1, y, z; (x) x, y+1, z; (xi) x, y+1, z; (xii) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A2···O1Ai0.972.553.150 (3)120
C14B—H14A···O3Aii0.972.593.418 (4)143
C14B—H14B···O5Bii0.972.573.163 (3)120
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A2···O1Ai0.972.553.150 (3)120
C14B—H14A···O3Aii0.972.593.418 (4)143
C14B—H14B···O5Bii0.972.573.163 (3)120
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1.
 

Acknowledgements

Chandra would like to thank the UGC, New Delhi, for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.

References

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