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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161877
https://doi.org/10.1107/S2414314616018770

N′-[(E)-4-Meth­­oxy­benzyl­­idene]-2-(4-methyl­phen­­oxy)acetohydrazide

CROSSMARK_Color_square_no_text.svg
Seranthimata Samshuddin,a S. Naveen,b Dandavathi Arunkumar,c A. Mahesha,c N. K. Lokanathd* and Muneer Abdohe*

aDepartment of Chemistry, SDM Institute of Technology, Ujire 574 240, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of P.G. Studies in Chemistry, Alva's College, Moodabidri 574 227, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and eDepartment of Physics, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, muneer@najah.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 November 2016; accepted 23 November 2016; online 29 November 2016)

The title compound, C17H18N2O3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the 4-meth­oxy­phenyl ring and the toluene ring is 88.13 (10)° in mol­ecule A and 61.47 (10)° in mol­ecule B. In the crystal, mol­ecules are linked via pairs of N—H⋯O hydrogen bonds, forming A–A and B–B inversion dimers with R22(8) ring motifs. The B–B dimers are linked by C—H⋯O hydrogen bonds, forming chains propagating along the [110] direction. The mol­ecules are also linked by a series of C—H⋯π inter­actions, forming a three-dimensional structure.

CCDC reference: 1518861

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

Structure description

A number of industrial and biologically active compounds can be synthesized by using Schiff bases as the substrates via cyclo­addition, ring closure and replacement reactions. In addition, Schiff bases are also known to have biological activities such as anti­fungal (Singh & Dash, 1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]) anti­microbial (El-masry et al., 2000[El-masry, A. H., Fahmy, H. H. & Ali Abdelwahed, S. H. (2000). Molecules, 5, 1429-1438.], Pandeya et al., 1999[Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.]), anti­tumor and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001[Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]), since many of these complexes may be useful and serve as the models for biologically important species. They have wide range of applications on the industrial scale such as dyes and pigments. In view of the importance of Schiff base hydrazones, we report herein on the synthesis and crystal structure of title compound.

The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound is shown in Fig. 1[link]. The dihedral angle between the 4-meth­oxy­phenyl ring and the toluene ring is 88.13 (10)° in mol­ecule A and 61.47 (10)° in mol­ecule B. The meth­oxy group in both mol­ecules lies in the plane of the phenyl ring as indicated by the torsion angles of 4.2 (3)° for C17A—O3A—C14A—C13A and −6.1 (2)° for C17B—O3B—C14B—C13B.

[Figure 1]
Figure 1
View of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, mol­ecules are linked via pairs of N—H⋯O hydrogen bonds forming A–A and B–B inversion dimers with [R_{2}^{2}](8) ring motifs (Fig. 2[link] and Table 1[link]). The B–B dimers are linked by C—H⋯O hydrogen bonds, forming chains propagating along [110]; see Table 1[link] and Fig. 3[link]. The mol­ecules are also linked by a series of C—H⋯π inter­actions (Table 1[link]), forming a three-dimensional structure.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2A–C7A, C11A–C16A, C2B–C7B and C11B–C16B rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1A⋯O2Ai 0.86 2.07 2.9226 (17) 173
N1B—H1B⋯O2Bii 0.86 2.07 2.9207 (17) 171
C17B—H17C⋯O1Biii 0.96 2.45 3.394 (2) 167
C3A—H3A⋯Cg3ii 0.93 2.95 3.549 (2) 123
C6A—H6A⋯Cg3i 0.93 2.98 3.698 (2) 135
C16B—H16B⋯Cg1 0.93 2.81 3.742 (2) 177
C17B—H17A⋯Cg2i 0.96 2.81 3.569 (2) 136
C17A—H17D⋯Cg4ii 0.96 2.93 3.619 (2) 130
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
A view of the pairs of N—H⋯O hydrogen bonds forming the A–A and B–B inversion dimers with [R_{2}^{2}](8) ring motifs (see Table 1[link]).
[Figure 3]
Figure 3
A view along the c axis of the crystal packing of the title compound (colour code: mol­ecule A blue, mol­ecule B red). The hydrogen bonds are shown as dashed lines (see Table 1[link]), and only the H atoms (grey balls) involved in hydrogen bonding have been included.

Synthesis and crystallization

A mixture of 2-(4-methyl­phen­oxy)acetohydrazide (1.8 g, 0.01 mol), anisaldehyde (1.36 g, 0.01 mol) and hydrazine hydrate (0.6 ml, 0.012 mol) in 15 ml of 2-propanol containing two drops of sulfuric acid, was refluxed for ca 3 h. On cooling, the solid that separated was filtered and recrystallized from DMF. On slow evaporation of the solvent colourless block-like crystals were obtained (yield 78%, m.p. 478 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C17H18N2O3
Mr 298.33
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 296
a, b, c (Å) 9.4835 (3), 11.9112 (4), 15.5727 (4)
α, β, γ (°) 72.136 (1), 86.122 (1), 70.688 (1)
V (Å3) 1578.95 (8)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.29 × 0.27 × 0.25
 
Data collection
Diffractometer Bruker APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections 21401, 5906, 3766
Rint 0.026
(sin θ/λ)max (Å−1) 0.609
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.128, 1.02
No. of reflections 5906
No. of parameters 401
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.13, −0.15
Computer programs: APEX2 and SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data

CCDC reference: 1518861

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616018770/su4099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018770/su4099Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018770/su4099Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

N'-[(E)-4-Methoxybenzylidene]-2-(4-methylphenoxy)acetohydrazide top
Crystal data top
C17H18N2O3Z = 4
Mr = 298.33F(000) = 632
Triclinic, P1Dx = 1.255 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4835 (3) ÅCell parameters from 3766 reflections
b = 11.9112 (4) Åθ = 2.0–25.7°
c = 15.5727 (4) ŵ = 0.09 mm−1
α = 72.136 (1)°T = 296 K
β = 86.122 (1)°Block, colourless
γ = 70.688 (1)°0.29 × 0.27 × 0.25 mm
V = 1578.95 (8) Å3
Data collection top
Bruker APEXII
diffractometer		5906 independent reflections
Radiation source: Enraf Nonius FR5903766 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 18.4 pixels mm-1θmax = 25.7°, θmin = 2.0°
CCD rotation images, thick slices scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2011)		k = −14→13
Tmin = 0.984, Tmax = 0.987l = −18→18
21401 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.068P)2 + 0.0979P]
where P = (Fo2 + 2Fc2)/3
5906 reflections(Δ/σ)max < 0.001
401 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
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 esds 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 > 2sigma(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
O1A0.62766 (15)−0.10667 (12)0.25322 (8)0.0693 (5)
O2A0.48929 (12)0.00034 (10)0.38205 (7)0.0523 (4)
O3A1.42111 (13)−0.61212 (11)0.69317 (8)0.0640 (4)
N1A0.67734 (14)−0.11448 (11)0.48438 (8)0.0473 (5)
N2A0.81426 (14)−0.20652 (11)0.50537 (9)0.0466 (4)
C1A0.7133 (4)0.3263 (3)0.00499 (19)0.1448 (16)
C2A0.6947 (3)0.2086 (2)0.07176 (14)0.0903 (9)
C3A0.7806 (2)0.1485 (2)0.15016 (15)0.0784 (8)
C4A0.7635 (2)0.04332 (18)0.21292 (12)0.0654 (7)
C5A0.65672 (19)−0.00312 (17)0.19669 (11)0.0567 (6)
C6A0.5715 (2)0.0539 (2)0.11750 (12)0.0763 (8)
C7A0.5910 (3)0.1585 (3)0.05705 (14)0.0952 (9)
C8A0.6934 (2)−0.15650 (16)0.34117 (11)0.0655 (7)
C9A0.61066 (17)−0.08207 (14)0.40320 (10)0.0439 (5)
C10A0.86917 (17)−0.23483 (14)0.58434 (11)0.0469 (5)
C11A1.01379 (17)−0.33017 (14)0.61346 (10)0.0445 (5)
C12A1.07332 (18)−0.36059 (15)0.69929 (11)0.0545 (6)
C13A1.20890 (19)−0.45358 (16)0.72909 (11)0.0554 (6)
C14A1.28807 (17)−0.51757 (14)0.67161 (11)0.0483 (5)
C15A1.2317 (2)−0.48595 (16)0.58491 (11)0.0617 (6)
C16A1.09718 (19)−0.39536 (15)0.55635 (11)0.0564 (6)
C17A1.4796 (2)−0.65423 (18)0.78254 (13)0.0728 (7)
O1B0.81558 (13)0.13675 (11)0.72848 (8)0.0634 (5)
O2B0.98466 (12)0.01561 (11)0.61375 (7)0.0603 (4)
O3B0.11002 (13)0.58182 (11)0.21213 (8)0.0640 (4)
N1B0.80908 (13)0.10968 (11)0.50178 (8)0.0479 (4)
N2B0.67169 (14)0.19796 (11)0.47024 (9)0.0464 (4)
C1B0.8441 (4)−0.2943 (3)1.02392 (17)0.1524 (13)
C2B0.8360 (2)−0.1803 (3)0.94423 (15)0.0907 (9)
C3B0.8593 (2)−0.0773 (3)0.95466 (14)0.0964 (12)
C4B0.8521 (2)0.0272 (2)0.88290 (14)0.0794 (9)
C5B0.81862 (18)0.03015 (17)0.79686 (11)0.0548 (6)
C6B0.7916 (2)−0.07031 (18)0.78532 (12)0.0651 (7)
C7B0.8018 (2)−0.1739 (2)0.85892 (14)0.0800 (8)
C8B0.75049 (19)0.15668 (16)0.64326 (11)0.0569 (6)
C9B0.85908 (18)0.08797 (14)0.58578 (10)0.0470 (6)
C10B0.63556 (17)0.21631 (14)0.38850 (10)0.0456 (5)
C11B0.49714 (17)0.31029 (14)0.34541 (10)0.0437 (5)
C12B0.40738 (18)0.39544 (15)0.38652 (11)0.0528 (6)
C13B0.27787 (19)0.48620 (16)0.34533 (11)0.0545 (6)
C14B0.23462 (17)0.49484 (14)0.25990 (10)0.0481 (6)
C15B0.32298 (19)0.41067 (15)0.21760 (11)0.0557 (6)
C16B0.45144 (19)0.31997 (15)0.25966 (11)0.0548 (6)
C17B0.0093 (2)0.66292 (16)0.25662 (13)0.0662 (7)
H1A0.63450−0.077700.523400.0570*
H3A0.853100.179500.161500.0940*
H4A0.823500.004500.265500.0780*
H1A10.752700.30900−0.049700.2170*
H6A0.501000.021700.105000.0920*
H1A20.780900.353000.030800.2170*
H7A0.531700.196800.004200.1140*
H1A30.617900.39100−0.008200.2170*
H8A10.79630−0.157500.338200.0790*
H8A20.69410−0.242000.366100.0790*
H10A0.81580−0.193700.624400.0560*
H12A1.02080−0.317300.738300.0650*
H13A1.24610−0.472600.787400.0670*
H151.28630−0.527100.545200.0740*
H16A1.06060−0.376900.497900.0680*
H17D1.49320−0.586100.797700.1090*
H17E1.57410−0.719300.787700.1090*
H17F1.41130−0.686000.823100.1090*
H1B10.94640−0.338201.044600.2280*
H1B0.862600.068600.467600.0570*
H1B20.80420−0.348201.005800.2280*
H1B30.78680−0.268601.071900.2280*
H3B0.88080−0.078101.012300.1160*
H8B10.716700.245300.611300.0680*
H4B0.869600.095100.892200.0950*
H8B20.663800.128900.652600.0680*
H6B0.76640−0.069000.728200.0780*
H7B0.78460−0.241900.849800.0960*
H10B0.699400.168300.355600.0550*
H12B0.435500.391100.443800.0630*
H13B0.219500.541600.374900.0650*
H15B0.295000.415600.160100.0670*
H16B0.509000.263900.230300.0660*
H17A−0.022000.614100.311000.0990*
H17B−0.076400.715600.217500.0990*
H17C0.058700.713600.271300.0990*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0851 (10)0.0679 (8)0.0536 (7)−0.0146 (7)−0.0097 (6)−0.0253 (7)
O2A0.0465 (7)0.0512 (7)0.0523 (7)−0.0065 (6)−0.0064 (5)−0.0145 (5)
O3A0.0514 (7)0.0578 (7)0.0666 (8)−0.0002 (6)−0.0040 (6)−0.0140 (6)
N1A0.0422 (8)0.0463 (8)0.0474 (8)−0.0051 (6)−0.0014 (6)−0.0153 (6)
N2A0.0428 (8)0.0410 (7)0.0500 (8)−0.0084 (6)−0.0011 (6)−0.0104 (6)
C1A0.130 (3)0.140 (3)0.119 (2)−0.043 (2)0.0296 (19)0.0176 (19)
C2A0.0645 (14)0.1090 (18)0.0666 (14)−0.0113 (13)0.0162 (12)−0.0051 (13)
C3A0.0530 (12)0.0982 (16)0.0811 (15)−0.0190 (11)0.0149 (11)−0.0319 (13)
C4A0.0507 (11)0.0791 (13)0.0564 (11)−0.0025 (10)−0.0043 (8)−0.0255 (10)
C5A0.0463 (10)0.0711 (12)0.0448 (10)−0.0008 (9)−0.0010 (8)−0.0257 (9)
C6A0.0575 (12)0.1120 (17)0.0502 (11)−0.0164 (12)−0.0063 (9)−0.0221 (12)
C7A0.0648 (14)0.139 (2)0.0517 (12)−0.0155 (14)−0.0048 (10)−0.0048 (13)
C8A0.0810 (13)0.0513 (11)0.0533 (11)−0.0023 (9)−0.0048 (9)−0.0200 (9)
C9A0.0453 (10)0.0380 (9)0.0466 (9)−0.0136 (8)−0.0016 (7)−0.0096 (7)
C10A0.0436 (9)0.0475 (9)0.0487 (10)−0.0111 (8)0.0021 (7)−0.0173 (8)
C11A0.0423 (9)0.0414 (9)0.0473 (9)−0.0132 (7)0.0004 (7)−0.0103 (7)
C12A0.0487 (10)0.0612 (11)0.0531 (10)−0.0095 (9)0.0007 (8)−0.0257 (9)
C13A0.0506 (10)0.0626 (11)0.0509 (10)−0.0138 (9)−0.0069 (8)−0.0174 (9)
C14A0.0412 (9)0.0418 (9)0.0557 (10)−0.0107 (8)0.0017 (8)−0.0091 (8)
C15A0.0626 (12)0.0592 (11)0.0496 (10)−0.0015 (9)0.0070 (9)−0.0184 (9)
C16A0.0593 (11)0.0567 (11)0.0417 (9)−0.0056 (9)−0.0011 (8)−0.0125 (8)
C17A0.0544 (12)0.0709 (13)0.0746 (13)−0.0051 (10)−0.0117 (10)−0.0101 (10)
O1B0.0652 (8)0.0699 (8)0.0634 (8)−0.0194 (6)−0.0090 (6)−0.0324 (7)
O2B0.0399 (7)0.0756 (8)0.0530 (7)−0.0063 (6)−0.0058 (5)−0.0140 (6)
O3B0.0532 (7)0.0641 (8)0.0594 (7)−0.0026 (6)−0.0110 (6)−0.0126 (6)
N1B0.0388 (7)0.0516 (8)0.0461 (8)−0.0066 (6)−0.0026 (6)−0.0129 (6)
N2B0.0392 (7)0.0460 (8)0.0490 (8)−0.0110 (6)−0.0023 (6)−0.0098 (6)
C1B0.123 (2)0.207 (3)0.0850 (18)−0.075 (2)−0.0123 (16)0.041 (2)
C2B0.0595 (13)0.140 (2)0.0596 (14)−0.0362 (14)0.0009 (10)−0.0076 (14)
C3B0.0687 (15)0.168 (3)0.0447 (12)−0.0283 (16)−0.0057 (10)−0.0310 (16)
C4B0.0650 (13)0.1193 (18)0.0658 (13)−0.0235 (12)−0.0068 (10)−0.0499 (13)
C5B0.0406 (9)0.0756 (13)0.0501 (10)−0.0111 (8)−0.0008 (7)−0.0297 (10)
C6B0.0693 (12)0.0877 (14)0.0474 (10)−0.0317 (11)0.0051 (8)−0.0270 (10)
C7B0.0797 (15)0.0969 (16)0.0651 (13)−0.0399 (12)0.0099 (11)−0.0162 (12)
C8B0.0534 (10)0.0603 (11)0.0568 (10)−0.0124 (9)−0.0070 (8)−0.0222 (9)
C9B0.0425 (10)0.0494 (10)0.0475 (10)−0.0172 (8)−0.0006 (7)−0.0094 (8)
C10B0.0434 (9)0.0468 (9)0.0454 (9)−0.0142 (7)0.0024 (7)−0.0130 (7)
C11B0.0434 (9)0.0436 (9)0.0428 (9)−0.0151 (7)0.0019 (7)−0.0103 (7)
C12B0.0495 (10)0.0608 (11)0.0425 (9)−0.0100 (9)−0.0029 (7)−0.0156 (8)
C13B0.0508 (10)0.0589 (11)0.0499 (10)−0.0096 (9)0.0040 (8)−0.0204 (8)
C14B0.0432 (9)0.0473 (10)0.0486 (10)−0.0139 (8)−0.0039 (7)−0.0069 (8)
C15B0.0599 (11)0.0589 (11)0.0455 (9)−0.0128 (9)−0.0093 (8)−0.0166 (8)
C16B0.0552 (11)0.0542 (10)0.0514 (10)−0.0078 (8)−0.0017 (8)−0.0210 (8)
C17B0.0514 (11)0.0553 (11)0.0814 (13)−0.0036 (9)−0.0063 (9)−0.0190 (10)
Geometric parameters (Å, º) top
O1A—C5A1.378 (2)C8A—H8A20.9700
O1A—C8A1.410 (2)C10A—H10A0.9300
O2A—C9A1.226 (2)C12A—H12A0.9300
O3A—C14A1.363 (2)C13A—H13A0.9300
O3A—C17A1.410 (2)C15A—H150.9300
O1B—C8B1.421 (2)C16A—H16A0.9300
O1B—C5B1.378 (2)C17A—H17F0.9600
O2B—C9B1.230 (2)C17A—H17D0.9600
O3B—C14B1.364 (2)C17A—H17E0.9600
O3B—C17B1.427 (2)C1B—C2B1.517 (4)
N1A—N2A1.3751 (19)C2B—C7B1.362 (3)
N1A—C9A1.340 (2)C2B—C3B1.374 (5)
N2A—C10A1.270 (2)C3B—C4B1.380 (3)
N1A—H1A0.8600C4B—C5B1.385 (3)
N1B—C9B1.3409 (19)C5B—C6B1.368 (3)
N1B—N2B1.3813 (19)C6B—C7B1.383 (3)
N2B—C10B1.275 (2)C8B—C9B1.516 (2)
N1B—H1B0.8600C10B—C11B1.454 (2)
C1A—C2A1.524 (4)C11B—C16B1.391 (2)
C2A—C7A1.371 (4)C11B—C12B1.385 (2)
C2A—C3A1.371 (3)C12B—C13B1.375 (3)
C3A—C4A1.383 (3)C13B—C14B1.382 (2)
C4A—C5A1.373 (3)C14B—C15B1.384 (2)
C5A—C6A1.376 (3)C15B—C16B1.372 (3)
C6A—C7A1.372 (4)C1B—H1B10.9600
C8A—C9A1.516 (2)C1B—H1B20.9600
C10A—C11A1.454 (2)C1B—H1B30.9600
C11A—C16A1.393 (2)C3B—H3B0.9300
C11A—C12A1.381 (2)C4B—H4B0.9300
C12A—C13A1.385 (3)C6B—H6B0.9300
C13A—C14A1.377 (2)C7B—H7B0.9300
C14A—C15A1.380 (2)C8B—H8B10.9700
C15A—C16A1.364 (3)C8B—H8B20.9700
C1A—H1A20.9600C10B—H10B0.9300
C1A—H1A10.9600C12B—H12B0.9300
C1A—H1A30.9600C13B—H13B0.9300
C3A—H3A0.9300C15B—H15B0.9300
C4A—H4A0.9300C16B—H16B0.9300
C6A—H6A0.9300C17B—H17A0.9600
C7A—H7A0.9300C17B—H17B0.9600
C8A—H8A10.9700C17B—H17C0.9600
C5A—O1A—C8A117.56 (15)H17D—C17A—H17E110.00
C14A—O3A—C17A118.43 (14)O3A—C17A—H17D109.00
C5B—O1B—C8B118.15 (14)O3A—C17A—H17E109.00
C14B—O3B—C17B117.61 (13)O3A—C17A—H17F109.00
N2A—N1A—C9A120.10 (13)H17D—C17A—H17F109.00
N1A—N2A—C10A116.76 (13)H17E—C17A—H17F109.00
N2A—N1A—H1A120.00C3B—C2B—C7B116.7 (2)
C9A—N1A—H1A120.00C1B—C2B—C3B121.8 (2)
N2B—N1B—C9B120.00 (13)C1B—C2B—C7B121.6 (3)
N1B—N2B—C10B115.87 (13)C2B—C3B—C4B122.5 (2)
C9B—N1B—H1B120.00C3B—C4B—C5B119.4 (2)
N2B—N1B—H1B120.00O1B—C5B—C6B124.87 (15)
C1A—C2A—C7A121.9 (2)O1B—C5B—C4B116.09 (17)
C1A—C2A—C3A121.2 (3)C4B—C5B—C6B119.04 (17)
C3A—C2A—C7A116.9 (2)C5B—C6B—C7B119.73 (17)
C2A—C3A—C4A122.4 (2)C2B—C7B—C6B122.7 (2)
C3A—C4A—C5A119.20 (18)O1B—C8B—C9B112.34 (15)
O1A—C5A—C6A115.23 (17)N1B—C9B—C8B115.72 (15)
C4A—C5A—C6A119.47 (18)O2B—C9B—C8B122.86 (14)
O1A—C5A—C4A125.29 (16)O2B—C9B—N1B121.41 (15)
C5A—C6A—C7A119.7 (2)N2B—C10B—C11B121.70 (15)
C2A—C7A—C6A122.4 (2)C12B—C11B—C16B117.24 (15)
O1A—C8A—C9A112.24 (15)C10B—C11B—C12B121.81 (14)
N1A—C9A—C8A115.43 (14)C10B—C11B—C16B120.94 (15)
O2A—C9A—N1A121.74 (14)C11B—C12B—C13B122.09 (15)
O2A—C9A—C8A122.81 (14)C12B—C13B—C14B119.87 (16)
N2A—C10A—C11A121.36 (15)O3B—C14B—C15B116.09 (14)
C12A—C11A—C16A117.31 (16)O3B—C14B—C13B124.99 (15)
C10A—C11A—C16A121.46 (14)C13B—C14B—C15B118.92 (16)
C10A—C11A—C12A121.23 (15)C14B—C15B—C16B120.67 (15)
C11A—C12A—C13A122.05 (16)C11B—C16B—C15B121.22 (16)
C12A—C13A—C14A119.41 (15)C2B—C1B—H1B1109.00
O3A—C14A—C15A115.78 (15)C2B—C1B—H1B2110.00
C13A—C14A—C15A119.13 (16)C2B—C1B—H1B3109.00
O3A—C14A—C13A125.09 (15)H1B1—C1B—H1B2110.00
C14A—C15A—C16A121.15 (16)H1B1—C1B—H1B3109.00
C11A—C16A—C15A120.92 (15)H1B2—C1B—H1B3109.00
H1A1—C1A—H1A2110.00C2B—C3B—H3B119.00
C2A—C1A—H1A1109.00C4B—C3B—H3B119.00
C2A—C1A—H1A2109.00C3B—C4B—H4B120.00
C2A—C1A—H1A3109.00C5B—C4B—H4B120.00
H1A1—C1A—H1A3109.00C5B—C6B—H6B120.00
H1A2—C1A—H1A3110.00C7B—C6B—H6B120.00
C2A—C3A—H3A119.00C2B—C7B—H7B119.00
C4A—C3A—H3A119.00C6B—C7B—H7B119.00
C3A—C4A—H4A120.00O1B—C8B—H8B1109.00
C5A—C4A—H4A120.00O1B—C8B—H8B2109.00
C5A—C6A—H6A120.00C9B—C8B—H8B1109.00
C7A—C6A—H6A120.00C9B—C8B—H8B2109.00
C6A—C7A—H7A119.00H8B1—C8B—H8B2108.00
C2A—C7A—H7A119.00N2B—C10B—H10B119.00
C9A—C8A—H8A2109.00C11B—C10B—H10B119.00
O1A—C8A—H8A1109.00C11B—C12B—H12B119.00
O1A—C8A—H8A2109.00C13B—C12B—H12B119.00
C9A—C8A—H8A1109.00C12B—C13B—H13B120.00
H8A1—C8A—H8A2108.00C14B—C13B—H13B120.00
N2A—C10A—H10A119.00C14B—C15B—H15B120.00
C11A—C10A—H10A119.00C16B—C15B—H15B120.00
C13A—C12A—H12A119.00C11B—C16B—H16B119.00
C11A—C12A—H12A119.00C15B—C16B—H16B119.00
C12A—C13A—H13A120.00O3B—C17B—H17A109.00
C14A—C13A—H13A120.00O3B—C17B—H17B109.00
C14A—C15A—H15119.00O3B—C17B—H17C109.00
C16A—C15A—H15119.00H17A—C17B—H17B110.00
C15A—C16A—H16A120.00H17A—C17B—H17C109.00
C11A—C16A—H16A120.00H17B—C17B—H17C109.00
C8A—O1A—C5A—C4A11.6 (3)C12A—C11A—C16A—C15A0.4 (3)
C8A—O1A—C5A—C6A−169.82 (17)C10A—C11A—C16A—C15A−178.99 (17)
C5A—O1A—C8A—C9A78.4 (2)C16A—C11A—C12A—C13A−1.2 (3)
C17A—O3A—C14A—C13A4.2 (3)C11A—C12A—C13A—C14A0.5 (3)
C17A—O3A—C14A—C15A−175.89 (16)C12A—C13A—C14A—C15A1.2 (3)
C5B—O1B—C8B—C9B−83.13 (19)C12A—C13A—C14A—O3A−178.86 (16)
C8B—O1B—C5B—C6B13.8 (3)C13A—C14A—C15A—C16A−2.1 (3)
C8B—O1B—C5B—C4B−166.35 (17)O3A—C14A—C15A—C16A177.98 (17)
C17B—O3B—C14B—C13B−6.1 (2)C14A—C15A—C16A—C11A1.3 (3)
C17B—O3B—C14B—C15B174.49 (16)C7B—C2B—C3B—C4B−1.4 (4)
C9A—N1A—N2A—C10A−178.18 (15)C1B—C2B—C3B—C4B−179.9 (3)
N2A—N1A—C9A—C8A2.3 (2)C1B—C2B—C7B—C6B179.1 (3)
N2A—N1A—C9A—O2A−179.33 (15)C3B—C2B—C7B—C6B0.5 (4)
N1A—N2A—C10A—C11A−179.54 (14)C2B—C3B—C4B—C5B0.7 (4)
N2B—N1B—C9B—O2B−175.47 (15)C3B—C4B—C5B—O1B−179.08 (19)
C9B—N1B—N2B—C10B177.21 (15)C3B—C4B—C5B—C6B0.8 (3)
N2B—N1B—C9B—C8B5.3 (2)C4B—C5B—C6B—C7B−1.6 (3)
N1B—N2B—C10B—C11B−177.30 (14)O1B—C5B—C6B—C7B178.25 (18)
C3A—C2A—C7A—C6A0.6 (4)C5B—C6B—C7B—C2B1.0 (3)
C1A—C2A—C7A—C6A−178.8 (3)O1B—C8B—C9B—O2B5.5 (2)
C7A—C2A—C3A—C4A−1.0 (4)O1B—C8B—C9B—N1B−175.26 (14)
C1A—C2A—C3A—C4A178.4 (2)N2B—C10B—C11B—C12B8.7 (3)
C2A—C3A—C4A—C5A−0.1 (3)N2B—C10B—C11B—C16B−172.91 (16)
C3A—C4A—C5A—C6A1.6 (3)C10B—C11B—C12B—C13B178.64 (17)
C3A—C4A—C5A—O1A−179.9 (2)C16B—C11B—C12B—C13B0.2 (3)
C4A—C5A—C6A—C7A−2.0 (3)C10B—C11B—C16B—C15B−178.20 (17)
O1A—C5A—C6A—C7A179.4 (2)C12B—C11B—C16B—C15B0.3 (3)
C5A—C6A—C7A—C2A0.9 (4)C11B—C12B—C13B—C14B−0.5 (3)
O1A—C8A—C9A—O2A9.7 (2)C12B—C13B—C14B—O3B−179.03 (16)
O1A—C8A—C9A—N1A−171.96 (15)C12B—C13B—C14B—C15B0.4 (3)
N2A—C10A—C11A—C16A−0.8 (3)O3B—C14B—C15B—C16B179.53 (16)
N2A—C10A—C11A—C12A179.88 (16)C13B—C14B—C15B—C16B0.0 (3)
C10A—C11A—C12A—C13A178.13 (17)C14B—C15B—C16B—C11B−0.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2A–C7A, C11A–C16A, C2B–C7B and C11B–C16B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2Ai0.862.072.9226 (17)173
N1B—H1B···O2Bii0.862.072.9207 (17)171
C17B—H17C···O1Biii0.962.453.394 (2)167
C3A—H3A···Cg3ii0.932.953.549 (2)123
C6A—H6A···Cg3i0.932.983.698 (2)135
C16B—H16B···Cg10.932.813.742 (2)177
C17B—H17A···Cg2i0.962.813.569 (2)136
C17A—H17D···Cg4ii0.962.933.619 (2)130
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+1, −z+1.
 

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161877
https://doi.org/10.1107/S2414314616018770
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