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ISSN: 2056-9890

N′-Benzoyl-5-methyl-1,3-di­phenyl-1H-pyrazole-4-carbohydrazide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and cDepartment of Physics, SJB Institute of Technology, Kengeri, Bangalore 560 060, India
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

(Received 11 October 2013; accepted 26 October 2013; online 13 November 2013)

In the title compound, C24H20N4O2, the pyrazole ring makes dihedral angles of 47.57 (10)° and 30.56 (11)° with its N-bound and C-bound phenyl groups, respectively. The C—N—N—C group that links the two carbonyls has a torsion angle of 81.5 (2)°. The torsion angles between the carbonyl groups and their adjacent pyrazole and phenyl rings are 125.89 (19) and 164.22 (17)°, respectively. In the crystal, pairs of mol­ecules are linked by N—H⋯O hydrogen bonds into R22(10) ring motifs, which in turn link to form chains that propagate parallel to the c-axis direction.

Related literature

For the biological activity of pyrazoles, see: Cunico et al. (2006[Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., Souza, M. V. N., Freitas, I. O., Soaresa, R. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. 16, 649-653.]); Farag et al. (2008[Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. Lett. 16, 881-889.]); Sharma et al. (2010[Sharma, P. K., Kumar, S., Kumar, P., Kaushik, P., Kaushik, D., Dhingra, Y. & Aneja, K. R. (2010). Eur. J. Med. Chem. 45, 2650-2655.]); Patel et al. (2004[Patel, M. V., Bell, R., Majest, S., Henry, R. & Kolasa, T. (2004). J. Org. Chem. 69, 7058-7065.]). For the synthesis of pyrazoles, see: Shridevi Doddaramappa et al. (2013[Shridevi Doddaramappa, D., Chandra, Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698-703.]). For bond-length and angle data in a related structure, see: Chandra et al. (2012[Chandra, , Srikantamurthy, N., Umesha, K. B., Jeyaseelan, S. & Mahendra, M. (2012). Acta Cryst. E68, o1661-o1662.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N4O2

  • Mr = 396.44

  • Monoclinic, P 21 /c

  • a = 22.399 (15) Å

  • b = 11.180 (8) Å

  • c = 8.190 (6) Å

  • β = 97.378 (12)°

  • V = 2034 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 18837 measured reflections

  • 3601 independent reflections

  • 2793 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.04

  • 3601 reflections

  • 280 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N21—H21⋯O20i 0.88 (2) 2.05 (2) 2.925 (3) 174.5 (17)
N22—H22⋯O24ii 0.90 (2) 1.98 (2) 2.864 (3) 167.7 (17)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

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

Compounds that contain the pyrazole moiety are known to exhibit a wide range of biological properties such as anti-malarial (Cunico et al., 2006), anti-tumor (Farag et al., 2008) and anti-inflammatory activities (Sharma et al., 2010). In addition, pyrazoles have a wide variety of application in the agrochemical and pharmaceutical industries (Patel et al., 2004). Recently we have reported the synthesis of substituted pyrazoles (Shridevi Doddaramappa et al., 2013). As an extension of our work on the structural characterization of pyrazoles, the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges and are comparable to those in a related structure (Chandra et al., 2012). The pyrazole moiety makes a torsion angle of 47.57 (10)° and 30.56 (11)° with the N-bound phenyl (C8–C13) and C-bound phenyl (C14–C19) groups, respectively. Also, the pyrazole ring makes a torsion angle of 51.36 (10)° with the amide group (C4/C19/O20/N21). The C-N-N-C group that links the two carbonyls has a torsion angle of 81.5 (2)°. Torsion angles between the carbonyl groups and their adjacent pyrazole and phenyl rings are 125.89 (19)° and 164.22 (17)°, respectively. In the crystal, pairs of molecules are linked by N—H···O hydrogen bonds into R22(10) ring motifs, which in turn link to form chains that propagate parallel to the c axis (Fig. 2).

Related literature top

For the biological activity of pyrazoles, see: Cunico et al. (2006); Farag et al. (2008); Sharma et al. (2010); Patel et al. (2004). For the synthesis of pyrazoles, see: Shridevi Doddaramappa et al. (2013). For bond-length and angle data in a related structure, see: Chandra et al. (2012).

Experimental top

To pyrazole 4-carboxylic acid in CH2Cl2 (5 ml), ethyl-(N',N'-dimethylamino)propylcarbodiimide hydrochloride (EDC·HCl, 1.2 mmol) and 1-hydroxybenzotriazole (HOBt, 1.2 mmol) and then benzohydrazide (0.136 g, 1.0 mmol) was added and stirred at 25° C for 8–12 h. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and the combined organic phase was washed with brine and dried over anhydrous sodium sulfate. Ethyl acetate was distilled off and the residue thus obtained was purified by column chromatography to give a white solid. The typical size of the block-shaped crystals was 0.30 × 0.25 × 0.20 mm.

Refinement top

Carbon-bound H atoms were positioned geometrically and allowed to ride on their parent atoms with C–H distances in the range of 0.93 to 0.96 Å, respectively. Uiso(H) values were set to 1.2–1.5Ueq of the attached atom. The coordinates of H-atoms attached to nitrogen were allowed to refine.

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 molecule with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the structure viewed down the 'b' axis.
N'-Benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide top
Crystal data top
C24H20N4O2F(000) = 832
Mr = 396.44Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3601 reflections
a = 22.399 (15) Åθ = 1.8–25.1°
b = 11.180 (8) ŵ = 0.09 mm1
c = 8.190 (6) ÅT = 293 K
β = 97.378 (12)°Block, white
V = 2034 (2) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.039
ω and ϕ scansθmax = 25.1°, θmin = 1.8°
18837 measured reflectionsh = 2626
3601 independent reflectionsk = 1313
2793 reflections with I > 2σ(I)l = 99
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.4179P]
where P = (Fo2 + 2Fc2)/3
3601 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C24H20N4O2V = 2034 (2) Å3
Mr = 396.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.399 (15) ŵ = 0.09 mm1
b = 11.180 (8) ÅT = 293 K
c = 8.190 (6) Å0.30 × 0.25 × 0.20 mm
β = 97.378 (12)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2793 reflections with I > 2σ(I)
18837 measured reflectionsRint = 0.039
3601 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.16 e Å3
3601 reflectionsΔρmin = 0.16 e Å3
280 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
O200.19942 (5)0.37324 (10)0.57237 (14)0.0459 (4)
O240.09764 (5)0.37966 (12)0.20756 (15)0.0542 (5)
N10.36194 (5)0.24500 (11)0.35566 (17)0.0386 (4)
N20.36205 (6)0.36600 (12)0.33447 (17)0.0412 (5)
N210.17262 (6)0.23024 (14)0.3828 (2)0.0464 (5)
N220.11216 (6)0.23944 (14)0.4056 (2)0.0453 (5)
C30.30808 (7)0.40197 (14)0.3675 (2)0.0372 (5)
C40.27321 (7)0.30316 (14)0.40903 (19)0.0354 (5)
C50.30905 (7)0.20387 (14)0.3993 (2)0.0365 (5)
C60.29699 (8)0.07602 (15)0.4324 (2)0.0495 (6)
C70.41505 (7)0.17858 (14)0.3349 (2)0.0408 (5)
C80.41110 (8)0.07649 (17)0.2407 (2)0.0532 (7)
C90.46268 (10)0.01246 (19)0.2225 (3)0.0669 (8)
C100.51756 (10)0.0515 (2)0.2948 (3)0.0713 (9)
C110.52135 (9)0.1549 (2)0.3862 (3)0.0696 (8)
C120.47012 (8)0.21913 (17)0.4085 (3)0.0555 (7)
C130.29037 (7)0.52833 (14)0.3435 (2)0.0408 (5)
C140.23106 (8)0.55850 (16)0.2907 (2)0.0485 (6)
C150.21515 (9)0.67597 (18)0.2585 (3)0.0660 (8)
C160.25768 (11)0.76367 (19)0.2758 (4)0.0855 (10)
C170.31656 (11)0.73563 (19)0.3275 (4)0.0847 (9)
C180.33299 (9)0.61860 (17)0.3625 (3)0.0612 (7)
C190.21258 (7)0.30730 (14)0.4629 (2)0.0360 (5)
C230.07792 (7)0.32262 (15)0.3178 (2)0.0410 (6)
C250.01545 (7)0.34010 (15)0.3583 (2)0.0402 (5)
C260.01345 (7)0.26058 (17)0.4520 (2)0.0460 (6)
C270.07082 (8)0.28462 (19)0.4886 (2)0.0558 (7)
C280.09995 (8)0.38720 (19)0.4304 (3)0.0584 (7)
C290.07218 (9)0.46552 (18)0.3351 (3)0.0593 (7)
C300.01473 (8)0.44250 (17)0.2992 (2)0.0523 (7)
H6A0.285500.035200.330100.0740*
H6B0.265000.070500.499700.0740*
H6C0.332700.039800.488700.0740*
H80.373900.050600.189300.0640*
H90.460000.057600.160800.0800*
H100.552200.008300.282300.0860*
H110.558800.182200.433700.0840*
H120.472900.288400.471900.0670*
H140.201800.499100.277000.0580*
H150.175100.695500.224600.0790*
H160.246700.842700.252500.1020*
H170.345600.795600.339100.1020*
H180.373000.600200.399200.0730*
H210.1796 (8)0.1945 (17)0.291 (3)0.058 (6)*
H220.1019 (8)0.2004 (17)0.494 (3)0.059 (6)*
H260.005900.190600.490400.0550*
H270.089700.231400.552600.0670*
H280.138400.403600.455500.0700*
H290.092200.534400.294600.0710*
H300.003800.496100.235000.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O200.0476 (7)0.0487 (7)0.0441 (7)0.0038 (6)0.0161 (6)0.0043 (6)
O240.0513 (8)0.0636 (8)0.0506 (8)0.0096 (6)0.0173 (6)0.0017 (6)
N10.0320 (7)0.0342 (7)0.0510 (9)0.0040 (6)0.0106 (6)0.0026 (6)
N20.0347 (8)0.0331 (8)0.0569 (9)0.0019 (6)0.0101 (6)0.0039 (6)
N210.0315 (8)0.0596 (10)0.0505 (10)0.0040 (7)0.0146 (7)0.0125 (8)
N220.0311 (8)0.0593 (10)0.0481 (9)0.0011 (7)0.0148 (7)0.0007 (8)
C30.0316 (9)0.0384 (9)0.0419 (9)0.0026 (7)0.0058 (7)0.0004 (7)
C40.0307 (8)0.0373 (9)0.0386 (9)0.0015 (7)0.0063 (7)0.0010 (7)
C50.0329 (8)0.0382 (9)0.0390 (9)0.0005 (7)0.0065 (7)0.0015 (7)
C60.0493 (11)0.0393 (10)0.0612 (12)0.0005 (8)0.0121 (9)0.0081 (8)
C70.0349 (9)0.0406 (9)0.0486 (10)0.0074 (7)0.0123 (8)0.0073 (8)
C80.0497 (11)0.0545 (11)0.0563 (12)0.0112 (9)0.0100 (9)0.0039 (9)
C90.0706 (15)0.0571 (12)0.0775 (15)0.0205 (11)0.0267 (12)0.0019 (11)
C100.0529 (13)0.0686 (15)0.0980 (18)0.0276 (11)0.0311 (12)0.0204 (13)
C110.0340 (11)0.0771 (15)0.0983 (17)0.0073 (10)0.0104 (10)0.0121 (13)
C120.0386 (10)0.0527 (11)0.0761 (14)0.0009 (9)0.0108 (9)0.0003 (10)
C130.0396 (9)0.0363 (9)0.0476 (10)0.0026 (7)0.0098 (7)0.0004 (7)
C140.0414 (10)0.0428 (10)0.0616 (12)0.0034 (8)0.0074 (8)0.0043 (9)
C150.0532 (12)0.0505 (12)0.0920 (17)0.0147 (10)0.0003 (11)0.0070 (11)
C160.0852 (18)0.0369 (12)0.128 (2)0.0097 (12)0.0110 (15)0.0049 (12)
C170.0768 (16)0.0395 (12)0.131 (2)0.0106 (11)0.0125 (15)0.0026 (13)
C180.0467 (11)0.0440 (11)0.0900 (16)0.0026 (9)0.0018 (10)0.0004 (10)
C190.0359 (9)0.0374 (9)0.0361 (9)0.0048 (7)0.0098 (7)0.0050 (7)
C230.0366 (9)0.0471 (10)0.0401 (10)0.0076 (8)0.0082 (8)0.0110 (8)
C250.0351 (9)0.0478 (10)0.0378 (9)0.0036 (7)0.0048 (7)0.0078 (8)
C260.0349 (9)0.0557 (11)0.0470 (10)0.0004 (8)0.0040 (8)0.0011 (8)
C270.0364 (10)0.0732 (13)0.0590 (12)0.0031 (9)0.0111 (9)0.0023 (10)
C280.0350 (10)0.0739 (14)0.0664 (13)0.0045 (10)0.0069 (9)0.0135 (11)
C290.0501 (11)0.0541 (12)0.0721 (14)0.0108 (9)0.0023 (10)0.0056 (10)
C300.0512 (11)0.0492 (11)0.0570 (12)0.0008 (9)0.0089 (9)0.0014 (9)
Geometric parameters (Å, º) top
O20—C191.226 (2)C17—C181.379 (3)
O24—C231.233 (2)C23—C251.492 (2)
N1—N21.364 (2)C25—C301.385 (3)
N1—C51.361 (2)C25—C261.388 (3)
N1—C71.431 (2)C26—C271.383 (3)
N2—C31.334 (2)C27—C281.374 (3)
N21—N221.394 (2)C28—C291.374 (3)
N21—C191.350 (2)C29—C301.381 (3)
N22—C231.352 (2)C6—H6A0.9600
N21—H210.88 (2)C6—H6B0.9600
N22—H220.90 (2)C6—H6C0.9600
C3—C131.474 (2)C8—H80.9300
C3—C41.419 (2)C9—H90.9300
C4—C191.482 (2)C10—H100.9300
C4—C51.378 (2)C11—H110.9300
C5—C61.486 (3)C12—H120.9300
C7—C81.374 (3)C14—H140.9300
C7—C121.378 (3)C15—H150.9300
C8—C91.383 (3)C16—H160.9300
C9—C101.366 (3)C17—H170.9300
C10—C111.374 (3)C18—H180.9300
C11—C121.386 (3)C26—H260.9300
C13—C181.384 (3)C27—H270.9300
C13—C141.385 (3)C28—H280.9300
C14—C151.377 (3)C29—H290.9300
C15—C161.362 (3)C30—H300.9300
C16—C171.369 (4)
O20···N222.690 (3)C8···H6A3.0300
O20···C133.413 (3)C8···H6C2.8800
O20···C143.246 (3)C9···H12ii3.0600
O20···C233.258 (3)C12···H9iv3.0400
O20···N21i2.925 (3)C13···H6Bii3.0100
O24···N22ii2.864 (3)C14···H6Bii2.9700
O24···C26ii3.420 (3)C19···H6B2.9000
O24···C193.205 (3)C19···H21i2.88 (2)
O24···N212.656 (3)C19···H142.6200
O20···H28iii2.8400C23···H26ii2.9500
O20···H142.8000C23···H22ii2.78 (2)
O20···H6Ai2.8600C25···H26ii3.0100
O20···H21i2.05 (2)C26···H222.649 (19)
O24···H302.5100C27···H15v2.9100
O24···H142.6800C28···H15v2.9100
O24···H212.793 (19)C30···H26ii3.0200
O24···H22ii1.98 (2)H6A···C83.0300
O24···H26ii2.6600H6A···H82.4200
N2···C8i3.428 (3)H6A···H16vi2.3800
N21···O242.656 (3)H6A···O20ii2.8600
N21···C63.257 (3)H6B···N212.8100
N21···O20ii2.925 (3)H6B···C192.9000
N22···O202.690 (3)H6B···C3i3.0600
N22···O24i2.864 (3)H6B···C13i3.0100
N2···H122.7300H6B···C14i2.9700
N2···H10iv2.7600H6C···C72.8300
N2···H182.6800H6C···C82.8800
N21···H6B2.8100H8···C52.9400
N22···H262.6200H8···C62.8100
N22···H29v2.8200H8···H6A2.4200
C3···C6ii3.549 (3)H8···C3ii2.9000
C3···C8i3.594 (4)H9···C12vii3.0400
C6···C13i3.584 (3)H10···N2vii2.7600
C6···C3i3.549 (3)H10···H18vii2.5900
C6···C83.167 (3)H12···N22.7300
C6···N213.257 (3)H12···C9i3.0600
C8···C3ii3.594 (4)H14···O202.8000
C8···N2ii3.428 (3)H14···O242.6800
C8···C63.167 (3)H14···C42.8400
C13···O203.413 (3)H14···C192.6200
C13···C6ii3.584 (3)H15···C27viii2.9100
C14···C193.193 (3)H15···C28viii2.9100
C14···O203.246 (3)H16···H6Aix2.3800
C19···C143.193 (3)H18···N22.6800
C19···O243.205 (3)H18···H10iv2.5900
C23···O203.258 (3)H21···O242.793 (19)
C23···C26ii3.529 (3)H21···C52.923 (19)
C25···C29iii3.439 (4)H21···C63.04 (2)
C25···C26ii3.494 (3)H21···O20ii2.05 (2)
C26···C25i3.494 (3)H21···C19ii2.88 (2)
C26···C23i3.529 (3)H22···C262.649 (19)
C26···O24i3.420 (3)H22···H262.1500
C29···C25iii3.439 (4)H22···O24i1.98 (2)
C29···C30iii3.510 (4)H22···C23i2.78 (2)
C30···C29iii3.510 (4)H26···N222.6200
C30···C30iii3.514 (3)H26···H222.1500
C3···H6Bii3.0600H26···O24i2.6600
C3···H8i2.9000H26···C23i2.9500
C4···H142.8400H26···C25i3.0100
C5···H82.9400H26···C30i3.0200
C5···H212.923 (19)H28···O20iii2.8400
C6···H213.04 (2)H29···N22viii2.8200
C6···H82.8100H30···O242.5100
C7···H6C2.8300
N2—N1—C5112.61 (12)C26—C25—C30118.78 (15)
N2—N1—C7118.98 (12)C25—C26—C27120.52 (17)
C5—N1—C7128.39 (13)C26—C27—C28120.01 (18)
N1—N2—C3104.87 (12)C27—C28—C29119.97 (18)
N22—N21—C19118.85 (15)C28—C29—C30120.31 (19)
N21—N22—C23118.28 (15)C25—C30—C29120.41 (17)
N22—N21—H21115.4 (12)C5—C6—H6A109.00
C19—N21—H21121.6 (12)C5—C6—H6B109.00
N21—N22—H22115.1 (12)C5—C6—H6C109.00
C23—N22—H22125.1 (12)H6A—C6—H6B110.00
N2—C3—C4110.78 (14)H6A—C6—H6C109.00
N2—C3—C13119.82 (14)H6B—C6—H6C110.00
C4—C3—C13129.13 (14)C7—C8—H8120.00
C3—C4—C5105.69 (14)C9—C8—H8120.00
C5—C4—C19127.26 (14)C8—C9—H9120.00
C3—C4—C19126.92 (14)C10—C9—H9120.00
N1—C5—C4106.04 (13)C9—C10—H10120.00
N1—C5—C6123.90 (14)C11—C10—H10120.00
C4—C5—C6130.04 (15)C10—C11—H11120.00
C8—C7—C12120.55 (16)C12—C11—H11120.00
N1—C7—C12119.23 (15)C7—C12—H12121.00
N1—C7—C8120.21 (14)C11—C12—H12121.00
C7—C8—C9119.73 (17)C13—C14—H14120.00
C8—C9—C10120.4 (2)C15—C14—H14120.00
C9—C10—C11119.6 (2)C14—C15—H15120.00
C10—C11—C12120.9 (2)C16—C15—H15120.00
C7—C12—C11118.80 (19)C15—C16—H16120.00
C3—C13—C14120.41 (15)C17—C16—H16120.00
C3—C13—C18120.93 (15)C16—C17—H17120.00
C14—C13—C18118.53 (16)C18—C17—H17120.00
C13—C14—C15120.41 (17)C13—C18—H18120.00
C14—C15—C16120.4 (2)C17—C18—H18120.00
C15—C16—C17120.1 (2)C25—C26—H26120.00
C16—C17—C18120.2 (2)C27—C26—H26120.00
C13—C18—C17120.43 (19)C26—C27—H27120.00
N21—C19—C4114.28 (14)C28—C27—H27120.00
O20—C19—N21122.18 (15)C27—C28—H28120.00
O20—C19—C4123.53 (14)C29—C28—H28120.00
O24—C23—C25121.98 (15)C28—C29—H29120.00
N22—C23—C25117.13 (14)C30—C29—H29120.00
O24—C23—N22120.88 (15)C25—C30—H30120.00
C23—C25—C26123.81 (15)C29—C30—H30120.00
C23—C25—C30117.41 (15)
C5—N1—N2—C30.71 (18)C5—C4—C19—O20125.89 (19)
C7—N1—N2—C3177.81 (14)C5—C4—C19—N2153.0 (2)
N2—N1—C5—C40.77 (18)N1—C7—C8—C9179.50 (17)
N2—N1—C5—C6179.13 (14)C12—C7—C8—C91.4 (3)
C7—N1—C5—C4177.58 (15)N1—C7—C12—C11179.31 (18)
C7—N1—C5—C60.8 (3)C8—C7—C12—C110.2 (3)
N2—N1—C7—C8132.39 (16)C7—C8—C9—C101.4 (3)
N2—N1—C7—C1246.7 (2)C8—C9—C10—C110.1 (3)
C5—N1—C7—C849.4 (2)C9—C10—C11—C121.1 (4)
C5—N1—C7—C12131.54 (19)C10—C11—C12—C71.1 (3)
N1—N2—C3—C40.36 (18)C3—C13—C14—C15175.98 (17)
N1—N2—C3—C13174.96 (14)C18—C13—C14—C150.2 (3)
C19—N21—N22—C2381.5 (2)C3—C13—C18—C17175.0 (2)
N22—N21—C19—O2010.8 (2)C14—C13—C18—C170.8 (3)
N22—N21—C19—C4170.27 (14)C13—C14—C15—C161.0 (3)
N21—N22—C23—O247.9 (2)C14—C15—C16—C170.8 (4)
N21—N22—C23—C25173.20 (15)C15—C16—C17—C180.1 (5)
N2—C3—C4—C50.09 (19)C16—C17—C18—C130.9 (4)
N2—C3—C4—C19176.06 (15)O24—C23—C25—C26164.22 (17)
C13—C3—C4—C5173.87 (16)O24—C23—C25—C3016.3 (2)
C13—C3—C4—C1910.0 (3)N22—C23—C25—C2614.7 (2)
N2—C3—C13—C14145.43 (16)N22—C23—C25—C30164.83 (16)
N2—C3—C13—C1830.3 (3)C23—C25—C26—C27178.06 (16)
C4—C3—C13—C1428.1 (3)C30—C25—C26—C271.4 (3)
C4—C3—C13—C18156.25 (19)C23—C25—C30—C29178.60 (17)
C3—C4—C5—N10.50 (17)C26—C25—C30—C290.9 (3)
C3—C4—C5—C6178.72 (16)C25—C26—C27—C280.8 (3)
C19—C4—C5—N1175.63 (15)C26—C27—C28—C290.4 (3)
C19—C4—C5—C62.6 (3)C27—C28—C29—C300.9 (3)
C3—C4—C19—O2049.4 (2)C28—C29—C30—C250.2 (3)
C3—C4—C19—N21131.63 (17)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x, y+1, z+1; (iv) x+1, y+1/2, z+1/2; (v) x, y1/2, z+1/2; (vi) x, y1, z; (vii) x+1, y1/2, z+1/2; (viii) x, y+1/2, z+1/2; (ix) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O20ii0.88 (2)2.05 (2)2.925 (3)174.5 (17)
N22—H22···O24i0.90 (2)1.98 (2)2.864 (3)167.7 (17)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O20i0.88 (2)2.05 (2)2.925 (3)174.5 (17)
N22—H22···O24ii0.90 (2)1.98 (2)2.864 (3)167.7 (17)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
 

Acknowledgements

The authors would like to thank the UGC, New Delhi, Government of India, for awarding a project under the head F. No. 41–920/2012(SR) dated: 25–07–2012.

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