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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages 377-379
doi:10.1107/S2056989015004569

Crystal structure of (2E)-2-meth­­oxy­imino-2-{2-[(2-methyl­phen­­oxy)meth­yl]phen­yl}-N′-(4-nitro­benzyl­­idene)ethano­hydrazide

CROSSMARK_Color_square_no_text.svg
Chetan Shrimandhar Shripanavara and Ray J. Butcherb*

aP.G. Department of Agrochemicals and Pest Management, Devchand College, Arjunnagar 591 237, M.S., India, and bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 2 March 2015; accepted 4 March 2015; online 18 March 2015)

The title compound, C24H22N4O5, crystallizes with two mol­ecules in the asymmetric unit (Z′ = 2) oriented almost perpendicular to each other [dihedral angle between the central core of each mol­ecule = 77.95 (3)°]. The two mol­ecules exhibit similar conformations with an extended structure. An intra­molecular C—H⋯N hydrogen bond occurs in each mol­ecule. The two mol­ecules are linked by a bifurcated N—H⋯(O,N) hydrogen bond involving the NH group in mol­ecule A as donor. They are further linked into a ribbon along the a-axis direction by further bifurcated N—H⋯(O,N) hydrogen bonds involving the NH group in mol­ecule B as donor. C—H⋯O inter­actions are also observed.

CCDC reference: 1052231

Similar articles

1. Chemical context

Kresoxim-methyl [systematic name: methyl (2E)-(meth­oxy­imino){2-[(2-methyl­phen­oxy)meth­yl]phen­yl}acetate] derivatives are broad spectrum fungicides (Anke et al., 1977[Anke, T., Oberwinkler, F., Steglich, W. & Schramm, G. (1977). J. Antibiot. 30, 806-810.]), have a site-specific action (Olaya et al., 1998[Olaya, G., Zheng, D. & Köller, W. (1998). Pestic. Sci. 54, 230-236.]) and exhibit high efficiency (Patel et al., 2012[Patel, J. S., Gudmestad, N. C., Meinhardt, S. & Adhikari, T. B. (2012). Crop Prot. 34, 37-41.]; Esteve-Turrillas et al., 2011[Esteve-Turrillas, F. A., Mercader, J. V., Agulló, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2011). J. Chromatogr. A 30, 4902-4909.]; Mercader et al., 2008[Mercader, J. V., Suárez-Pantaleón, C., Agulló, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2008). J. Agric. Food Chem. 56, 7682-7690.]) against various diseases of agricultural crops (Balba, 2007[Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.]; Cash & Cronan, 2001[Cash, H. & Cronan, J. M. Jr (2001). US Patent Appl. WO2001-US9649 20010323.]; Ammermann et al., 2000[Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the BCPC Conference on Pest and Diseases, 2, 541-548.]). As these types of compounds are easily metabolized in nature as well as in living systems, their modifications are of immense importance (Balba, 2007[Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.]). In order to increases the activity of starting compounds (Kant et al., 2012[Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2426.]), it is necessary to modify their structures and to undertake a structural investigation of different kresoxim-methyl derivatives.

[Scheme 1]

2. Structural commentary

The title compound crystallizes with two mol­ecules in the asymmetric unit (Z′ = 2) labeled A and B and shown in Fig. 1[link]. The two mol­ecules exhibit similar conformations having an extended structure. In mol­ecule A, the nitro group is coplanar with the p-nitro­phenyl ring [deviations for N1A, O1A and O2A of 0.067 (2), 0.119 (2) and 0.089 (2) Å, respectively]. The central ethane hydrazide moiety (N2A/N3A/C8A/O3A) is strictly planar with an r.m.s. deviation of 0.000 Å for the fitted atoms. The dihedral angles between this moiety and the adjacent aromatic are 18.99 (4)° for the nitro­benzylidene ring (C1A–C6A) and 62.20 (4)° for the benzene ring (C11A–C16A).

[Figure 1]
Figure 1
The mol­ecular structure of mol­ecules A and B of the title compound, showing the atom labeling and displacement ellipsoids at the 30% probability level. Hydrogen bonds are shown as dashed lines. All H atoms, except those involved in hydrogen bonding, have been omitted for clarity.

In mol­ecule B, the nitro group is coplanar with the p-nitro­phenyl ring [deviations for N1B, O1B and O2B of 0.026 (2), 0.043 (2) and 0.127 (2) Å, respectively]. The central ethane hydrazide moiety (N2B/N3B/C8B/O3B) is planar (r.m.s. deviation = 0.002 Å). The dihedral angles between this moiety and the adjacent aromatic rings are 12.43 (4)° for the nitrobenzylidene ring (C1B–C6B) and 57.99 (4)° for the benzene ring (C11B–C16B).

Mol­ecules A and B are oriented almost perpendicular to each other, the dihedral angle between their central cores (atoms C7 N2 N3 and C8) being 77.95 (3)°.

For both mol­ecules, bond lengths and angles are all within the normal ranges; however, comparisons with similar mol­ecules cannot be made as there are no similar overall structures although, of course, their fragments exist.

An intra­molecular hydrogen bond (C17A—H17B⋯N4A and C17B—H17C⋯N4B; Table 1[link]) occurs in each independent mol­ecule.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3A—H3A⋯O3B 0.871 (17) 2.117 (17) 2.8679 (13) 144.0 (14)
N3A—H3A⋯N2B 0.871 (17) 2.432 (16) 3.1530 (14) 140.5 (13)
C7A—H7AA⋯O3B 0.95 2.47 3.1523 (14) 129
C10A—H10C⋯O1Bi 0.98 2.46 3.3159 (18) 145
N3B—H3B⋯O3Aii 0.901 (16) 2.068 (16) 2.8605 (13) 146.1 (13)
N3B—H3B⋯N2Aii 0.901 (16) 2.444 (15) 3.1598 (14) 136.6 (12)
C5B—H5BA⋯O2Aiii 0.95 2.63 3.3484 (18) 133
C7B—H7BA⋯O3Aii 0.95 2.51 3.1864 (14) 128
C17B—H17C⋯N4B 0.99 2.63 3.2436 (15) 120
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) -x, -y+1, -z+1.

3. Supra­molecular features

The two independent mol­ecules are linked by a bifurcated hydrogen bond (Table 1[link]) between N3A—H3A⋯(O3B,N2B). The mol­ecules are further linked into a ribbon along the a-axis direction a bifurcated N3B—H3B⋯(O3A,N2A)(x + 1, y, z) hydrogen bond involving the corresponding NH group in the other independent mol­ecule, as shown in Fig. 2[link]. C—H⋯O inter­actions link the ribbons into a three-dimensional array.

[Figure 2]
Figure 2
Diagram showing the two mol­ecules (A and B) linked by a bifurcated hydrogen bond between the N3A—H3A group and atoms O3B and N2B, and further linked into a ribbon along the a-axis direction by a bifurcated hydrogen bond between the N3B—H3B group and atoms O3A and N2A (generated by the symmetry operation x + 1, y, z).

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.35, last update November 2014; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) for the basic skeleton of this compound gave no hits.

5. Synthesis and crystallization

(2E)-2-Meth­oxy­imino-2-{2-[(2-methyl­phen­oxy)meth­yl]phenyl}ethane­hydrazide (3.13 g, 0.01 mol) was refluxed with p-nitro­benzaldehyde (1.51 g, 0.01 mol) in the presence of 5 drops of glacial acetic acid in 20 ml absolute ethanol for about 10 h to get a white-colored product. This was dissolved in methanol and white crystals were obtained by slow evaporation.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Amine H atoms were refined isotropically. All other H atoms were positioned geometric­ally and refined as riding: C—H = 0.93–0.99 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C24H22N4O5
Mr 446.45
Crystal system, space group Monoclinic, P21/n
Temperature (K) 120
a, b, c (Å) 7.6821 (4), 23.2151 (12), 25.1943 (15)
β (°) 95.803 (2)
V (Å3) 4470.1 (4)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.45 × 0.21 × 0.14
 
Data collection
Diffractometer Bruker APEXII
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.692, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 34631, 11046, 8755
Rint 0.031
(sin θ/λ)max (Å−1) 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.094, 1.02
No. of reflections 11046
No. of parameters 607
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.35, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SUPERFLIP (Palatinus & Chapuis 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1052231

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015004569/hg5434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004569/hg5434Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015004569/hg5434Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2E)-2-Methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}-N'-(4-nitrobenzylidene)ethanohydrazide top
Crystal data top
C24H22N4O5F(000) = 1872
Mr = 446.45Dx = 1.327 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.6821 (4) ÅCell parameters from 9882 reflections
b = 23.2151 (12) Åθ = 2.4–28.2°
c = 25.1943 (15) ŵ = 0.10 mm−1
β = 95.803 (2)°T = 120 K
V = 4470.1 (4) Å3Needle, colourless
Z = 80.45 × 0.21 × 0.14 mm
Data collection top
Bruker APEXII
diffractometer		8755 reflections with I > 2σ(I)
ω scansRint = 0.031
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		θmax = 28.3°, θmin = 2.4°
Tmin = 0.692, Tmax = 0.746h = −10→10
34631 measured reflectionsk = −30→30
11046 independent reflectionsl = −33→33
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0372P)2 + 1.7501P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
11046 reflectionsΔρmax = 0.35 e Å−3
607 parametersΔρmin = −0.22 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A−0.26253 (16)0.40731 (5)0.53333 (5)0.0423 (3)
O2A−0.02317 (16)0.36271 (4)0.51986 (4)0.0405 (3)
O3A0.09946 (11)0.75766 (4)0.62417 (3)0.01910 (18)
O4A0.63124 (11)0.82755 (4)0.69184 (3)0.01848 (18)
O5A0.58188 (11)0.87760 (4)0.52350 (3)0.02218 (19)
N1A−0.10267 (18)0.40448 (5)0.53527 (4)0.0303 (3)
N2A0.21581 (12)0.64878 (4)0.61833 (4)0.01462 (19)
N3A0.32523 (13)0.69387 (4)0.63413 (4)0.01431 (19)
H3A0.437 (2)0.6869 (7)0.6411 (6)0.030 (4)*
N4A0.52650 (13)0.78002 (4)0.67838 (4)0.0158 (2)
C1A0.18827 (16)0.55055 (5)0.59120 (4)0.0175 (2)
C2A0.27370 (18)0.50151 (6)0.57471 (5)0.0233 (3)
H2AA0.39770.50140.57570.028*
C3A0.17973 (19)0.45306 (6)0.55686 (5)0.0251 (3)
H3AA0.23750.41980.54550.030*
C4A0.00012 (19)0.45453 (5)0.55613 (5)0.0231 (3)
C5A−0.08892 (18)0.50194 (6)0.57312 (5)0.0245 (3)
H5AA−0.21270.50140.57280.029*
C6A0.00629 (17)0.55002 (5)0.59056 (5)0.0210 (3)
H6AA−0.05250.58300.60220.025*
C7A0.29202 (15)0.60136 (5)0.60856 (4)0.0167 (2)
H7AA0.41610.59920.61260.020*
C8A0.25467 (15)0.74729 (5)0.63586 (4)0.0141 (2)
C9A0.38222 (15)0.79508 (5)0.65171 (4)0.0141 (2)
C10A0.78988 (17)0.80896 (6)0.72185 (6)0.0283 (3)
H10A0.85570.84260.73620.042*
H10B0.86080.78720.69860.042*
H10C0.76150.78430.75130.042*
C11A0.32872 (15)0.85461 (5)0.63561 (5)0.0161 (2)
C12A0.18674 (16)0.87956 (6)0.65749 (5)0.0227 (3)
H12A0.13050.85930.68370.027*
C13A0.12772 (17)0.93369 (6)0.64103 (6)0.0287 (3)
H13A0.03350.95110.65680.034*
C14A0.20638 (18)0.96246 (6)0.60155 (6)0.0285 (3)
H14A0.16230.99870.58900.034*
C15A0.34927 (18)0.93837 (5)0.58034 (5)0.0234 (3)
H15A0.40310.95860.55360.028*
C16A0.41512 (16)0.88485 (5)0.59776 (5)0.0172 (2)
C17A0.58044 (16)0.86198 (5)0.57803 (4)0.0179 (2)
H17A0.68390.87850.59940.022*
H17B0.58490.81950.58180.022*
C18A0.73512 (16)0.86995 (5)0.50045 (5)0.0180 (2)
C19A0.89187 (17)0.85147 (6)0.52730 (5)0.0221 (3)
H19A0.89940.84300.56440.027*
C20A1.03816 (17)0.84545 (6)0.49918 (6)0.0262 (3)
H20A1.14610.83300.51730.031*
C21A1.02759 (18)0.85741 (6)0.44521 (6)0.0273 (3)
H21A1.12790.85360.42630.033*
C22A0.86849 (18)0.87511 (5)0.41876 (5)0.0232 (3)
H22A0.86130.88270.38160.028*
C23A0.72052 (17)0.88192 (5)0.44540 (5)0.0191 (2)
C24A0.54785 (18)0.89964 (6)0.41707 (5)0.0238 (3)
H24A0.55860.90320.37880.036*
H24B0.51270.93680.43100.036*
H24C0.45940.87050.42290.036*
O1B0.38132 (18)0.77311 (5)0.32876 (4)0.0468 (3)
O2B0.15770 (17)0.74670 (6)0.36820 (5)0.0509 (3)
O3B0.62240 (11)0.63511 (4)0.68689 (3)0.01902 (18)
O4B1.16718 (11)0.66162 (4)0.77511 (3)0.01737 (17)
O5B1.15483 (11)0.48146 (4)0.72363 (3)0.01938 (18)
N1B0.31493 (19)0.75518 (5)0.36773 (4)0.0308 (3)
N2B0.70567 (12)0.68705 (4)0.59787 (4)0.01368 (19)
N3B0.82799 (13)0.67735 (4)0.64094 (4)0.01422 (19)
H3B0.939 (2)0.6897 (6)0.6404 (6)0.023 (4)*
N4B1.04705 (12)0.67334 (4)0.73131 (4)0.01504 (19)
C1B0.64769 (15)0.71712 (5)0.50724 (4)0.0149 (2)
C2B0.71807 (17)0.73457 (5)0.46063 (5)0.0211 (3)
H2BA0.84130.73750.46030.025*
C3B0.60910 (19)0.74755 (5)0.41500 (5)0.0237 (3)
H3BA0.65620.75960.38340.028*
C4B0.43094 (18)0.74257 (5)0.41647 (5)0.0213 (3)
C5B0.35669 (17)0.72551 (6)0.46181 (5)0.0224 (3)
H5BA0.23330.72260.46180.027*
C6B0.46675 (16)0.71285 (5)0.50711 (5)0.0189 (2)
H6BA0.41840.70110.53860.023*
C7B0.76688 (15)0.70484 (5)0.55520 (4)0.0151 (2)
H7BA0.88940.71010.55470.018*
C8B0.77310 (15)0.65102 (5)0.68428 (4)0.0135 (2)
C9B0.91295 (14)0.64002 (5)0.72976 (4)0.0135 (2)
C10B1.30753 (16)0.70259 (6)0.77600 (5)0.0228 (3)
H10D1.38090.69980.81010.034*
H10E1.25910.74160.77190.034*
H10F1.37840.69440.74670.034*
C11B0.87970 (14)0.59275 (5)0.76739 (4)0.0136 (2)
C12B0.73387 (15)0.59676 (5)0.79640 (5)0.0168 (2)
H12B0.66190.63010.79320.020*
C13B0.69440 (16)0.55214 (6)0.82974 (5)0.0193 (2)
H13B0.59720.55530.85010.023*
C14B0.79674 (16)0.50289 (5)0.83340 (5)0.0197 (2)
H14B0.76770.47190.85560.024*
C15B0.94123 (16)0.49860 (5)0.80488 (5)0.0174 (2)
H15B1.01060.46460.80760.021*
C16B0.98577 (15)0.54373 (5)0.77224 (4)0.0141 (2)
C17B1.15104 (15)0.53835 (5)0.74491 (5)0.0157 (2)
H17C1.15140.56710.71590.019*
H17D1.25490.54500.77080.019*
C18B1.30751 (16)0.46297 (5)0.70551 (4)0.0173 (2)
C19B1.45797 (16)0.49618 (6)0.70528 (5)0.0202 (2)
H19B1.46040.53450.71860.024*
C20B1.60527 (17)0.47275 (6)0.68534 (5)0.0262 (3)
H20B1.70910.49500.68560.031*
C21B1.60113 (19)0.41739 (7)0.66519 (6)0.0316 (3)
H21B1.70100.40170.65110.038*
C22B1.44928 (19)0.38478 (6)0.66570 (5)0.0285 (3)
H22B1.44730.34670.65190.034*
C23B1.30058 (17)0.40636 (5)0.68578 (5)0.0208 (3)
C24B1.13482 (19)0.37187 (6)0.68574 (6)0.0277 (3)
H24D1.14970.33460.66850.042*
H24E1.03810.39290.66610.042*
H24F1.10860.36560.72260.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0443 (7)0.0344 (6)0.0491 (7)−0.0186 (5)0.0097 (5)−0.0134 (5)
O2A0.0595 (8)0.0217 (5)0.0416 (6)−0.0068 (5)0.0120 (5)−0.0129 (4)
O3A0.0119 (4)0.0179 (4)0.0267 (4)−0.0008 (3)−0.0017 (3)0.0026 (3)
O4A0.0147 (4)0.0185 (4)0.0211 (4)−0.0050 (3)−0.0039 (3)−0.0009 (3)
O5A0.0194 (4)0.0303 (5)0.0167 (4)0.0004 (4)0.0012 (3)0.0059 (3)
N1A0.0474 (8)0.0215 (6)0.0227 (6)−0.0116 (5)0.0074 (5)−0.0043 (4)
N2A0.0138 (5)0.0159 (5)0.0140 (4)−0.0033 (4)0.0002 (4)0.0004 (4)
N3A0.0093 (5)0.0158 (5)0.0175 (5)−0.0017 (4)−0.0002 (4)−0.0010 (4)
N4A0.0142 (5)0.0171 (5)0.0159 (5)−0.0045 (4)0.0009 (4)−0.0011 (4)
C1A0.0214 (6)0.0169 (6)0.0135 (5)−0.0003 (5)−0.0017 (4)−0.0002 (4)
C2A0.0242 (7)0.0221 (6)0.0224 (6)0.0044 (5)−0.0038 (5)−0.0023 (5)
C3A0.0362 (8)0.0179 (6)0.0201 (6)0.0056 (6)−0.0029 (5)−0.0028 (5)
C4A0.0376 (8)0.0172 (6)0.0142 (5)−0.0070 (5)0.0016 (5)−0.0011 (4)
C5A0.0258 (7)0.0245 (7)0.0239 (6)−0.0065 (5)0.0052 (5)−0.0043 (5)
C6A0.0229 (6)0.0183 (6)0.0223 (6)−0.0023 (5)0.0044 (5)−0.0046 (5)
C7A0.0138 (5)0.0193 (6)0.0165 (5)0.0013 (5)−0.0006 (4)−0.0006 (4)
C8A0.0121 (5)0.0171 (5)0.0129 (5)−0.0018 (4)0.0012 (4)0.0019 (4)
C9A0.0126 (5)0.0161 (5)0.0138 (5)−0.0014 (4)0.0020 (4)−0.0002 (4)
C10A0.0185 (6)0.0311 (7)0.0325 (7)−0.0036 (6)−0.0113 (5)0.0013 (6)
C11A0.0135 (5)0.0148 (5)0.0192 (5)−0.0006 (4)−0.0032 (4)−0.0028 (4)
C12A0.0148 (6)0.0224 (6)0.0305 (7)−0.0012 (5)0.0016 (5)−0.0049 (5)
C13A0.0166 (6)0.0222 (7)0.0463 (8)0.0031 (5)−0.0014 (6)−0.0099 (6)
C14A0.0257 (7)0.0147 (6)0.0425 (8)0.0040 (5)−0.0097 (6)−0.0027 (5)
C15A0.0279 (7)0.0153 (6)0.0255 (6)−0.0016 (5)−0.0047 (5)0.0006 (5)
C16A0.0193 (6)0.0144 (5)0.0168 (5)−0.0024 (5)−0.0033 (4)−0.0025 (4)
C17A0.0225 (6)0.0152 (5)0.0159 (5)−0.0013 (5)0.0015 (4)0.0016 (4)
C18A0.0186 (6)0.0159 (6)0.0192 (6)−0.0037 (5)0.0012 (4)0.0006 (4)
C19A0.0227 (6)0.0229 (6)0.0199 (6)−0.0030 (5)−0.0024 (5)0.0005 (5)
C20A0.0181 (6)0.0276 (7)0.0319 (7)−0.0028 (5)−0.0028 (5)−0.0036 (5)
C21A0.0228 (7)0.0281 (7)0.0323 (7)−0.0045 (6)0.0087 (5)−0.0040 (6)
C22A0.0299 (7)0.0203 (6)0.0202 (6)−0.0053 (5)0.0058 (5)0.0008 (5)
C23A0.0235 (6)0.0138 (5)0.0197 (6)−0.0043 (5)0.0009 (5)0.0019 (4)
C24A0.0285 (7)0.0242 (6)0.0178 (6)−0.0007 (5)−0.0018 (5)0.0050 (5)
O1B0.0826 (9)0.0361 (6)0.0180 (5)−0.0131 (6)−0.0128 (5)0.0090 (4)
O2B0.0429 (7)0.0751 (9)0.0307 (6)0.0191 (7)−0.0162 (5)−0.0011 (6)
O3B0.0124 (4)0.0228 (4)0.0212 (4)−0.0031 (3)−0.0016 (3)0.0059 (3)
O4B0.0134 (4)0.0196 (4)0.0177 (4)−0.0032 (3)−0.0056 (3)0.0028 (3)
O5B0.0167 (4)0.0159 (4)0.0262 (4)0.0012 (3)0.0048 (3)−0.0049 (3)
N1B0.0534 (8)0.0185 (5)0.0175 (5)0.0063 (5)−0.0112 (5)−0.0022 (4)
N2B0.0113 (4)0.0140 (5)0.0149 (4)0.0010 (4)−0.0026 (3)−0.0001 (3)
N3B0.0088 (4)0.0176 (5)0.0157 (5)−0.0002 (4)−0.0018 (3)0.0005 (4)
N4B0.0127 (5)0.0172 (5)0.0144 (4)0.0015 (4)−0.0029 (4)−0.0001 (4)
C1B0.0189 (6)0.0112 (5)0.0145 (5)−0.0018 (4)0.0009 (4)−0.0015 (4)
C2B0.0243 (6)0.0217 (6)0.0178 (6)−0.0082 (5)0.0044 (5)−0.0026 (5)
C3B0.0396 (8)0.0178 (6)0.0139 (5)−0.0088 (6)0.0035 (5)−0.0009 (4)
C4B0.0362 (7)0.0121 (5)0.0137 (5)0.0020 (5)−0.0064 (5)−0.0013 (4)
C5B0.0201 (6)0.0247 (6)0.0214 (6)0.0033 (5)−0.0029 (5)−0.0007 (5)
C6B0.0184 (6)0.0223 (6)0.0159 (5)0.0005 (5)0.0013 (4)0.0030 (4)
C7B0.0119 (5)0.0162 (5)0.0172 (5)−0.0018 (4)0.0017 (4)−0.0022 (4)
C8B0.0122 (5)0.0112 (5)0.0167 (5)0.0020 (4)−0.0009 (4)−0.0010 (4)
C9B0.0116 (5)0.0131 (5)0.0155 (5)0.0022 (4)0.0001 (4)−0.0012 (4)
C10B0.0177 (6)0.0265 (7)0.0229 (6)−0.0095 (5)−0.0049 (5)0.0022 (5)
C11B0.0126 (5)0.0150 (5)0.0124 (5)−0.0012 (4)−0.0024 (4)−0.0009 (4)
C12B0.0134 (5)0.0178 (6)0.0187 (5)0.0016 (5)−0.0009 (4)−0.0021 (4)
C13B0.0139 (6)0.0258 (6)0.0186 (6)−0.0029 (5)0.0027 (4)−0.0006 (5)
C14B0.0186 (6)0.0212 (6)0.0191 (6)−0.0049 (5)0.0002 (5)0.0045 (5)
C15B0.0167 (6)0.0154 (5)0.0193 (6)0.0011 (5)−0.0014 (4)0.0012 (4)
C16B0.0132 (5)0.0156 (5)0.0127 (5)−0.0006 (4)−0.0018 (4)−0.0016 (4)
C17B0.0157 (5)0.0136 (5)0.0177 (5)0.0014 (4)0.0012 (4)−0.0012 (4)
C18B0.0180 (6)0.0190 (6)0.0145 (5)0.0053 (5)−0.0002 (4)0.0004 (4)
C19B0.0188 (6)0.0234 (6)0.0179 (6)0.0019 (5)0.0001 (5)−0.0018 (5)
C20B0.0164 (6)0.0392 (8)0.0226 (6)0.0023 (6)0.0002 (5)−0.0034 (5)
C21B0.0223 (7)0.0431 (9)0.0296 (7)0.0138 (6)0.0040 (5)−0.0054 (6)
C22B0.0320 (7)0.0250 (7)0.0279 (7)0.0123 (6)−0.0003 (6)−0.0060 (5)
C23B0.0245 (6)0.0189 (6)0.0183 (6)0.0051 (5)−0.0014 (5)0.0000 (4)
C24B0.0335 (8)0.0172 (6)0.0325 (7)−0.0005 (6)0.0029 (6)−0.0032 (5)
Geometric parameters (Å, º) top
O1A—N1A1.2258 (17)O1B—N1B1.2242 (17)
O2A—N1A1.2296 (16)O2B—N1B1.2250 (18)
O3A—C8A1.2228 (14)O3B—C8B1.2233 (14)
O4A—N4A1.3873 (13)O4B—N4B1.3918 (12)
O4A—C10A1.4341 (15)O4B—C10B1.4361 (14)
O5A—C18A1.3758 (15)O5B—C18B1.3700 (14)
O5A—C17A1.4222 (14)O5B—C17B1.4266 (14)
N1A—C4A1.4716 (17)N1B—C4B1.4719 (16)
N2A—C7A1.2823 (15)N2B—C7B1.2844 (15)
N2A—N3A1.3759 (14)N2B—N3B1.3803 (13)
N3A—C8A1.3560 (15)N3B—C8B1.3552 (15)
N3A—H3A0.871 (17)N3B—H3B0.901 (16)
N4A—C9A1.2853 (15)N4B—C9B1.2856 (15)
C1A—C6A1.3965 (17)C1B—C6B1.3932 (17)
C1A—C2A1.3982 (17)C1B—C2B1.4013 (16)
C1A—C7A1.4654 (17)C1B—C7B1.4683 (16)
C2A—C3A1.3865 (19)C2B—C3B1.3852 (18)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.378 (2)C3B—C4B1.378 (2)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.3864 (19)C4B—C5B1.3852 (18)
C5A—C6A1.3815 (18)C5B—C6B1.3816 (17)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.5072 (16)C8B—C9B1.5110 (15)
C9A—C11A1.4864 (16)C9B—C11B1.4892 (16)
C10A—H10A0.9800C10B—H10D0.9800
C10A—H10B0.9800C10B—H10E0.9800
C10A—H10C0.9800C10B—H10F0.9800
C11A—C12A1.3965 (17)C11B—C16B1.3979 (16)
C11A—C16A1.4039 (17)C11B—C12B1.4012 (16)
C12A—C13A1.3851 (19)C12B—C13B1.3865 (17)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.386 (2)C13B—C14B1.3854 (18)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.386 (2)C14B—C15B1.3855 (17)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.3954 (17)C15B—C16B1.3956 (16)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.5065 (17)C16B—C17B1.5094 (16)
C17A—H17A0.9900C17B—H17C0.9900
C17A—H17B0.9900C17B—H17D0.9900
C18A—C19A1.3881 (18)C18B—C19B1.3899 (18)
C18A—C23A1.4076 (16)C18B—C23B1.4040 (17)
C19A—C20A1.3947 (19)C19B—C20B1.3941 (18)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.382 (2)C20B—C21B1.381 (2)
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.394 (2)C21B—C22B1.392 (2)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.3863 (18)C22B—C23B1.3888 (18)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.4989 (18)C23B—C24B1.5040 (19)
C24A—H24A0.9800C24B—H24D0.9800
C24A—H24B0.9800C24B—H24E0.9800
C24A—H24C0.9800C24B—H24F0.9800
N4A—O4A—C10A109.30 (9)N4B—O4B—C10B108.64 (8)
C18A—O5A—C17A117.74 (9)C18B—O5B—C17B117.78 (9)
O1A—N1A—O2A123.86 (12)O1B—N1B—O2B123.61 (12)
O1A—N1A—C4A118.11 (12)O1B—N1B—C4B118.07 (13)
O2A—N1A—C4A118.01 (13)O2B—N1B—C4B118.32 (12)
C7A—N2A—N3A115.55 (10)C7B—N2B—N3B115.65 (10)
C8A—N3A—N2A118.07 (10)C8B—N3B—N2B117.68 (10)
C8A—N3A—H3A123.4 (11)C8B—N3B—H3B121.9 (9)
N2A—N3A—H3A118.4 (11)N2B—N3B—H3B120.4 (9)
C9A—N4A—O4A111.07 (9)C9B—N4B—O4B111.82 (9)
C6A—C1A—C2A119.26 (11)C6B—C1B—C2B119.21 (11)
C6A—C1A—C7A121.62 (11)C6B—C1B—C7B121.81 (10)
C2A—C1A—C7A119.12 (11)C2B—C1B—C7B118.97 (11)
C3A—C2A—C1A120.81 (12)C3B—C2B—C1B120.43 (12)
C3A—C2A—H2AA119.6C3B—C2B—H2BA119.8
C1A—C2A—H2AA119.6C1B—C2B—H2BA119.8
C4A—C3A—C2A118.16 (12)C4B—C3B—C2B118.56 (11)
C4A—C3A—H3AA120.9C4B—C3B—H3BA120.7
C2A—C3A—H3AA120.9C2B—C3B—H3BA120.7
C3A—C4A—C5A122.68 (12)C3B—C4B—C5B122.63 (11)
C3A—C4A—N1A119.05 (12)C3B—C4B—N1B118.70 (12)
C5A—C4A—N1A118.26 (13)C5B—C4B—N1B118.67 (12)
C6A—C5A—C4A118.54 (13)C6B—C5B—C4B118.26 (12)
C6A—C5A—H5AA120.7C6B—C5B—H5BA120.9
C4A—C5A—H5AA120.7C4B—C5B—H5BA120.9
C5A—C6A—C1A120.53 (12)C5B—C6B—C1B120.92 (11)
C5A—C6A—H6AA119.7C5B—C6B—H6BA119.5
C1A—C6A—H6AA119.7C1B—C6B—H6BA119.5
N2A—C7A—C1A120.21 (11)N2B—C7B—C1B120.04 (10)
N2A—C7A—H7AA119.9N2B—C7B—H7BA120.0
C1A—C7A—H7AA119.9C1B—C7B—H7BA120.0
O3A—C8A—N3A123.75 (11)O3B—C8B—N3B123.56 (10)
O3A—C8A—C9A120.72 (10)O3B—C8B—C9B120.83 (10)
N3A—C8A—C9A115.50 (10)N3B—C8B—C9B115.58 (10)
N4A—C9A—C11A126.56 (10)N4B—C9B—C11B127.77 (10)
N4A—C9A—C8A116.19 (10)N4B—C9B—C8B115.32 (10)
C11A—C9A—C8A117.24 (10)C11B—C9B—C8B116.91 (10)
O4A—C10A—H10A109.5O4B—C10B—H10D109.5
O4A—C10A—H10B109.5O4B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
O4A—C10A—H10C109.5O4B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C12A—C11A—C16A120.16 (11)C16B—C11B—C12B119.89 (10)
C12A—C11A—C9A118.91 (11)C16B—C11B—C9B121.31 (10)
C16A—C11A—C9A120.90 (10)C12B—C11B—C9B118.74 (10)
C13A—C12A—C11A120.22 (12)C13B—C12B—C11B120.11 (11)
C13A—C12A—H12A119.9C13B—C12B—H12B119.9
C11A—C12A—H12A119.9C11B—C12B—H12B119.9
C12A—C13A—C14A119.90 (13)C14B—C13B—C12B119.98 (11)
C12A—C13A—H13A120.0C14B—C13B—H13B120.0
C14A—C13A—H13A120.0C12B—C13B—H13B120.0
C13A—C14A—C15A120.12 (12)C15B—C14B—C13B120.25 (11)
C13A—C14A—H14A119.9C15B—C14B—H14B119.9
C15A—C14A—H14A119.9C13B—C14B—H14B119.9
C14A—C15A—C16A120.92 (12)C14B—C15B—C16B120.58 (11)
C14A—C15A—H15A119.5C14B—C15B—H15B119.7
C16A—C15A—H15A119.5C16B—C15B—H15B119.7
C15A—C16A—C11A118.54 (11)C15B—C16B—C11B119.15 (11)
C15A—C16A—C17A120.06 (11)C15B—C16B—C17B118.32 (10)
C11A—C16A—C17A121.34 (10)C11B—C16B—C17B122.50 (10)
O5A—C17A—C16A108.55 (10)O5B—C17B—C16B107.34 (9)
O5A—C17A—H17A110.0O5B—C17B—H17C110.2
C16A—C17A—H17A110.0C16B—C17B—H17C110.2
O5A—C17A—H17B110.0O5B—C17B—H17D110.2
C16A—C17A—H17B110.0C16B—C17B—H17D110.2
H17A—C17A—H17B108.4H17C—C17B—H17D108.5
O5A—C18A—C19A124.84 (11)O5B—C18B—C19B124.60 (11)
O5A—C18A—C23A113.83 (11)O5B—C18B—C23B114.10 (11)
C19A—C18A—C23A121.32 (11)C19B—C18B—C23B121.30 (11)
C18A—C19A—C20A119.16 (12)C18B—C19B—C20B119.39 (12)
C18A—C19A—H19A120.4C18B—C19B—H19B120.3
C20A—C19A—H19A120.4C20B—C19B—H19B120.3
C21A—C20A—C19A120.62 (13)C21B—C20B—C19B120.41 (13)
C21A—C20A—H20A119.7C21B—C20B—H20B119.8
C19A—C20A—H20A119.7C19B—C20B—H20B119.8
C20A—C21A—C22A119.41 (12)C20B—C21B—C22B119.40 (12)
C20A—C21A—H21A120.3C20B—C21B—H21B120.3
C22A—C21A—H21A120.3C22B—C21B—H21B120.3
C23A—C22A—C21A121.64 (12)C23B—C22B—C21B121.88 (13)
C23A—C22A—H22A119.2C23B—C22B—H22B119.1
C21A—C22A—H22A119.2C21B—C22B—H22B119.1
C22A—C23A—C18A117.83 (12)C22B—C23B—C18B117.61 (12)
C22A—C23A—C24A122.02 (11)C22B—C23B—C24B122.36 (12)
C18A—C23A—C24A120.12 (11)C18B—C23B—C24B120.02 (11)
C23A—C24A—H24A109.5C23B—C24B—H24D109.5
C23A—C24A—H24B109.5C23B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C23A—C24A—H24C109.5C23B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C7A—N2A—N3A—C8A168.52 (10)C7B—N2B—N3B—C8B−170.95 (10)
C10A—O4A—N4A—C9A179.55 (10)C10B—O4B—N4B—C9B−176.53 (10)
C6A—C1A—C2A—C3A1.25 (18)C6B—C1B—C2B—C3B0.15 (18)
C7A—C1A—C2A—C3A−178.53 (11)C7B—C1B—C2B—C3B−178.76 (11)
C1A—C2A—C3A—C4A−0.35 (19)C1B—C2B—C3B—C4B−0.39 (18)
C2A—C3A—C4A—C5A−0.91 (19)C2B—C3B—C4B—C5B0.46 (19)
C2A—C3A—C4A—N1A177.51 (11)C2B—C3B—C4B—N1B−178.76 (11)
O1A—N1A—C4A—C3A−177.67 (12)O1B—N1B—C4B—C3B−4.50 (17)
O2A—N1A—C4A—C3A0.95 (18)O2B—N1B—C4B—C3B174.85 (13)
O1A—N1A—C4A—C5A0.82 (18)O1B—N1B—C4B—C5B176.25 (12)
O2A—N1A—C4A—C5A179.44 (12)O2B—N1B—C4B—C5B−4.41 (18)
C3A—C4A—C5A—C6A1.21 (19)C3B—C4B—C5B—C6B−0.27 (19)
N1A—C4A—C5A—C6A−177.22 (11)N1B—C4B—C5B—C6B178.95 (11)
C4A—C5A—C6A—C1A−0.26 (19)C4B—C5B—C6B—C1B0.01 (19)
C2A—C1A—C6A—C5A−0.93 (18)C2B—C1B—C6B—C5B0.05 (18)
C7A—C1A—C6A—C5A178.84 (11)C7B—C1B—C6B—C5B178.92 (11)
N3A—N2A—C7A—C1A−179.72 (9)N3B—N2B—C7B—C1B−179.29 (10)
C6A—C1A—C7A—N2A−7.33 (17)C6B—C1B—C7B—N2B3.31 (17)
C2A—C1A—C7A—N2A172.45 (11)C2B—C1B—C7B—N2B−177.82 (11)
N2A—N3A—C8A—O3A0.00 (16)N2B—N3B—C8B—O3B0.70 (17)
N2A—N3A—C8A—C9A−178.06 (9)N2B—N3B—C8B—C9B178.48 (9)
O4A—N4A—C9A—C11A0.81 (16)O4B—N4B—C9B—C11B−1.30 (16)
O4A—N4A—C9A—C8A−178.51 (9)O4B—N4B—C9B—C8B178.23 (9)
O3A—C8A—C9A—N4A159.45 (11)O3B—C8B—C9B—N4B−158.18 (11)
N3A—C8A—C9A—N4A−22.43 (14)N3B—C8B—C9B—N4B23.97 (14)
O3A—C8A—C9A—C11A−19.94 (15)O3B—C8B—C9B—C11B21.41 (15)
N3A—C8A—C9A—C11A158.18 (10)N3B—C8B—C9B—C11B−156.45 (10)
N4A—C9A—C11A—C12A−113.93 (14)N4B—C9B—C11B—C16B−64.63 (16)
C8A—C9A—C11A—C12A65.38 (14)C8B—C9B—C11B—C16B115.84 (12)
N4A—C9A—C11A—C16A68.15 (16)N4B—C9B—C11B—C12B118.44 (13)
C8A—C9A—C11A—C16A−112.54 (12)C8B—C9B—C11B—C12B−61.09 (14)
C16A—C11A—C12A—C13A1.55 (18)C16B—C11B—C12B—C13B−0.20 (17)
C9A—C11A—C12A—C13A−176.39 (11)C9B—C11B—C12B—C13B176.77 (10)
C11A—C12A—C13A—C14A2.0 (2)C11B—C12B—C13B—C14B−1.59 (18)
C12A—C13A—C14A—C15A−3.1 (2)C12B—C13B—C14B—C15B1.63 (18)
C13A—C14A—C15A—C16A0.6 (2)C13B—C14B—C15B—C16B0.12 (18)
C14A—C15A—C16A—C11A2.83 (18)C14B—C15B—C16B—C11B−1.89 (17)
C14A—C15A—C16A—C17A−174.24 (12)C14B—C15B—C16B—C17B176.07 (11)
C12A—C11A—C16A—C15A−3.91 (17)C12B—C11B—C16B—C15B1.92 (16)
C9A—C11A—C16A—C15A173.99 (11)C9B—C11B—C16B—C15B−174.98 (10)
C12A—C11A—C16A—C17A173.11 (11)C12B—C11B—C16B—C17B−175.95 (10)
C9A—C11A—C16A—C17A−8.98 (17)C9B—C11B—C16B—C17B7.15 (16)
C18A—O5A—C17A—C16A168.60 (10)C18B—O5B—C17B—C16B−168.30 (9)
C15A—C16A—C17A—O5A−37.34 (15)C15B—C16B—C17B—O5B44.51 (13)
C11A—C16A—C17A—O5A145.68 (11)C11B—C16B—C17B—O5B−137.60 (10)
C17A—O5A—C18A—C19A−4.23 (17)C17B—O5B—C18B—C19B−1.51 (16)
C17A—O5A—C18A—C23A174.92 (10)C17B—O5B—C18B—C23B179.35 (10)
O5A—C18A—C19A—C20A179.98 (12)O5B—C18B—C19B—C20B−179.43 (11)
C23A—C18A—C19A—C20A0.89 (19)C23B—C18B—C19B—C20B−0.35 (18)
C18A—C19A—C20A—C21A−0.3 (2)C18B—C19B—C20B—C21B1.04 (19)
C19A—C20A—C21A—C22A−0.6 (2)C19B—C20B—C21B—C22B−1.0 (2)
C20A—C21A—C22A—C23A1.0 (2)C20B—C21B—C22B—C23B0.2 (2)
C21A—C22A—C23A—C18A−0.43 (19)C21B—C22B—C23B—C18B0.44 (19)
C21A—C22A—C23A—C24A−178.58 (12)C21B—C22B—C23B—C24B179.00 (13)
O5A—C18A—C23A—C22A−179.71 (11)O5B—C18B—C23B—C22B178.79 (11)
C19A—C18A—C23A—C22A−0.52 (18)C19B—C18B—C23B—C22B−0.38 (18)
O5A—C18A—C23A—C24A−1.52 (16)O5B—C18B—C23B—C24B0.20 (16)
C19A—C18A—C23A—C24A177.66 (12)C19B—C18B—C23B—C24B−178.97 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O3B0.871 (17)2.117 (17)2.8679 (13)144.0 (14)
N3A—H3A···N2B0.871 (17)2.432 (16)3.1530 (14)140.5 (13)
C7A—H7AA···O3B0.952.473.1523 (14)129
C10A—H10C···O1Bi0.982.463.3159 (18)145
C17A—H17B···N4A0.992.683.2243 (15)115
N3B—H3B···O3Aii0.901 (16)2.068 (16)2.8605 (13)146.1 (13)
N3B—H3B···N2Aii0.901 (16)2.444 (15)3.1598 (14)136.6 (12)
C5B—H5BA···O2Aiii0.952.633.3484 (18)133
C7B—H7BA···O3Aii0.952.513.1864 (14)128
C17B—H17C···N4B0.992.633.2436 (15)120
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1.
 

Acknowledgements

RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.

References

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ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages 377-379
doi:10.1107/S2056989015004569
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