organic compounds
(Z)-N′-[(E)-4-Methoxybenzylidene]-2-(methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetohydrazide
aChetan S Laboratory Pvt. LTD Pattankudi-591238, Karnataka, India, and bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com
The title compound, C25H25N3O4, crystallizes with two molecules in the In both molecules, the central ethane hydrazide moiety is almost planar. In the crystal, asymmetric, bifurcated N—H⋯(N,O) hydrogen bonds link the molecules into [100] chains. The packing is consolidated by weak C—H⋯O interactions.
Keywords: crystal structure; kresoxim-methyl derivatives; fungicide.
CCDC reference: 2020760
Structure description
Kresoxim-methyl derivatives (Cao et al., 2017) are broad-spectrum fungicides (e.g., Grossmann & Retzlaff, 1997), have a site-specific action (Olaya et al., 1998) and high efficiency (Patel et al., 2012) against various diseases of agricultural crops (Balba, 2007). As these types of compounds are easily metabolized in nature as well as in living systems, their modifications are of importance in order to improve their activity (Balba, 2007). In order to increase the activity of the starting compounds (Kant et al. 2012), it is necessary to modify the basic skeleton and initiate a structural investigation of different derivatives of kresoxim-methyl derivatives and in that light we previously reported the of a related derivative, (2E)-2-methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}-N′-(4-nitrobenzylidene)ethanohydrazide (Shripanavar & Butcher, 2015). This paper is a continuation in this series.
The title compound crystallizes with two molecules, A and B, in the as shown in Fig. 1. Both molecules exhibit similar conformations. For molecule A, the central ethane hydrazide moiety N2A/N3A/C17A/O3A is close to planar with an r.m.s. deviation of 0.02 Å for the fitted atoms. The dihedral angles between these atoms and the adjacent rings are 17.1 (2)° (C19A methoxyphenyl ring) and 79.9 (2)° (C14A benzene ring). This latter ring and the C1A toluyl ring are almost perpendicular, with a dihedral angle of 82.1 (1)°
For molecule B, the central ethane hydrazide moiety N2B/N3B/C17B/O3B is also close to planar, with an r.m.s. deviation of 0.01 Å for the fitted atoms. The equivalent dihedral angles to those in molecule A are 13.3 (2), 80.5 (2) and 86.1 (1)°, respectively.
In the crystal, bifurcated, asymmetric N—H⋯(N,O) hydrogen bonds (Table 1) link alternating A and B molecules into a zigzag chain propagating in the a-axis direction, as shown in Fig. 2. It is of interest that the shorter bond is to an O atom in one of these links and to an N atom in the other. The packing is consolidated by weak C—H⋯O interactions.
A search for related structures resulted in two close matches. The first is the parent azide from which the current structure is derived (Chopra et al., 2004) and the second is that with a nitro substituent instead of a methoxy substituent on the phenyl ring (CSD refcode JUFCIY; Shripanavar & Butcher, 2015). The major difference between the methoxy and nitro derivatives lies in the dihedral angles between the central benzene rings and the o-tolyl groups at the other end of the molecule: in the current structure these are 82.1 (1) and 86.1 (1)° while in JUFCIY the equivalent angles are 46.98 (5) and 48.23 (4)°.
Synthesis and crystallization
(2E)-2-(Methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}ethanohydrazide (3.13 g, 0.01 mol) was refluxed for 8 h with p-methoxybenzaldehyde (1.36 g, 0.01 mol) in 20 ml of absolute ethanol with the addition of 5 drops of glacial acetic acid to obtain a white-colored product. This was dissolved in DMSO and, by the process of slow evaporation, colourless needles of the title compound grew.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 2020760
https://doi.org/10.1107/S2414314620010603/hb4356sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620010603/hb4356Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620010603/hb4356Isup3.cml
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXT (Sheldrick 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).C25H25N3O4 | Dx = 1.270 Mg m−3 |
Mr = 431.48 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3813 reflections |
a = 7.8041 (6) Å | θ = 2.7–21.7° |
b = 22.8879 (16) Å | µ = 0.09 mm−1 |
c = 25.2670 (16) Å | T = 100 K |
V = 4513.2 (5) Å3 | Needle, colorless |
Z = 8 | 0.55 × 0.10 × 0.08 mm |
F(000) = 1824 |
Bruker APEXII CCD diffractometer | 6150 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.118 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.3°, θmin = 1.8° |
Tmin = 0.370, Tmax = 0.746 | h = −10→10 |
21010 measured reflections | k = −30→30 |
11096 independent reflections | l = 0→33 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: mixed |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3 |
11096 reflections | (Δ/σ)max < 0.001 |
591 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. H atoms were positioned geometrically and refined as riding: C–H = 0.95–0.98 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms. Amine H atoms were refined isotropically. The absolute structure could not be determined in the present refinement. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.1243 (4) | 0.63579 (12) | 0.58797 (10) | 0.0203 (7) | |
O2A | 0.4283 (4) | 0.59609 (12) | 0.50663 (11) | 0.0248 (7) | |
O3A | −0.0986 (4) | 0.54505 (12) | 0.44415 (10) | 0.0199 (7) | |
O4A | −0.1398 (4) | 0.23532 (12) | 0.23792 (11) | 0.0256 (7) | |
N1A | 0.3155 (5) | 0.55457 (15) | 0.48668 (13) | 0.0206 (8) | |
N2A | 0.1290 (5) | 0.48652 (15) | 0.42402 (13) | 0.0176 (8) | |
H2NA | 0.241 (6) | 0.487 (2) | 0.4155 (17) | 0.032 (14)* | |
N3A | 0.0302 (4) | 0.44522 (14) | 0.39725 (13) | 0.0168 (8) | |
C1A | 0.0846 (6) | 0.61249 (17) | 0.63698 (16) | 0.0198 (10) | |
C2A | −0.0757 (6) | 0.59077 (18) | 0.65070 (16) | 0.0234 (11) | |
H2AA | −0.165550 | 0.589987 | 0.625330 | 0.028* | |
C3A | −0.1039 (7) | 0.57024 (19) | 0.70162 (17) | 0.0311 (12) | |
H3AA | −0.213469 | 0.555692 | 0.711348 | 0.037* | |
C4A | 0.0281 (7) | 0.5710 (2) | 0.73823 (18) | 0.0352 (13) | |
H4AA | 0.009174 | 0.556932 | 0.773108 | 0.042* | |
C5A | 0.1868 (7) | 0.59222 (19) | 0.72408 (17) | 0.0295 (12) | |
H5AA | 0.276160 | 0.592626 | 0.749602 | 0.035* | |
C6A | 0.2192 (6) | 0.61295 (19) | 0.67364 (16) | 0.0226 (11) | |
C7A | 0.3921 (6) | 0.6368 (2) | 0.65789 (17) | 0.0302 (11) | |
H7AA | 0.473484 | 0.631143 | 0.686986 | 0.045* | |
H7AB | 0.381862 | 0.678614 | 0.650086 | 0.045* | |
H7AC | 0.433331 | 0.616202 | 0.626368 | 0.045* | |
C8A | −0.0129 (5) | 0.63901 (19) | 0.54977 (15) | 0.0205 (10) | |
H8AA | −0.111818 | 0.660116 | 0.565160 | 0.025* | |
H8AB | −0.050807 | 0.599158 | 0.540039 | 0.025* | |
C9A | 0.0504 (5) | 0.67058 (17) | 0.50159 (15) | 0.0162 (9) | |
C10A | 0.0117 (5) | 0.72957 (18) | 0.49412 (17) | 0.0209 (10) | |
H10A | −0.050877 | 0.750007 | 0.520526 | 0.025* | |
C11A | 0.0631 (6) | 0.75865 (19) | 0.44895 (16) | 0.0230 (10) | |
H11A | 0.033926 | 0.798619 | 0.444264 | 0.028* | |
C12A | 0.1562 (6) | 0.72999 (19) | 0.41069 (16) | 0.0235 (11) | |
H12A | 0.191614 | 0.750215 | 0.379728 | 0.028* | |
C13A | 0.1986 (5) | 0.67155 (19) | 0.41732 (16) | 0.0200 (10) | |
H13A | 0.264424 | 0.651960 | 0.391140 | 0.024* | |
C14A | 0.1445 (5) | 0.64151 (17) | 0.46245 (15) | 0.0150 (9) | |
C15A | 0.1822 (5) | 0.57772 (18) | 0.46630 (15) | 0.0165 (9) | |
C16A | 0.5739 (6) | 0.5653 (2) | 0.52806 (19) | 0.0363 (13) | |
H16A | 0.651842 | 0.593312 | 0.544900 | 0.054* | |
H16B | 0.634176 | 0.544977 | 0.499461 | 0.054* | |
H16C | 0.534777 | 0.536864 | 0.554370 | 0.054* | |
C17A | 0.0559 (5) | 0.53533 (18) | 0.44343 (15) | 0.0170 (9) | |
C18A | 0.1193 (6) | 0.40439 (17) | 0.37641 (15) | 0.0185 (10) | |
H18A | 0.238680 | 0.403264 | 0.383728 | 0.022* | |
C19A | 0.0478 (5) | 0.35954 (17) | 0.34207 (15) | 0.0171 (9) | |
C20A | −0.1141 (6) | 0.36428 (18) | 0.31907 (16) | 0.0199 (10) | |
H20A | −0.184670 | 0.396864 | 0.327234 | 0.024* | |
C21A | −0.1724 (5) | 0.32207 (18) | 0.28458 (16) | 0.0209 (10) | |
H21A | −0.282790 | 0.325688 | 0.269081 | 0.025* | |
C22A | −0.0700 (6) | 0.27419 (18) | 0.27242 (16) | 0.0204 (10) | |
C23A | 0.0922 (6) | 0.26902 (18) | 0.29479 (16) | 0.0225 (10) | |
H23A | 0.162775 | 0.236427 | 0.286587 | 0.027* | |
C24A | 0.1494 (6) | 0.31165 (18) | 0.32895 (16) | 0.0216 (10) | |
H24A | 0.260637 | 0.308325 | 0.343902 | 0.026* | |
C25A | −0.0391 (6) | 0.18549 (18) | 0.22374 (17) | 0.0271 (11) | |
H25A | −0.107942 | 0.158933 | 0.201989 | 0.041* | |
H25B | −0.001838 | 0.165182 | 0.255892 | 0.041* | |
H25C | 0.061612 | 0.198218 | 0.203624 | 0.041* | |
O1B | 0.6249 (4) | 0.60868 (13) | 0.20834 (11) | 0.0309 (8) | |
O2B | 0.9256 (4) | 0.56148 (12) | 0.28949 (11) | 0.0228 (7) | |
O3B | 0.4078 (4) | 0.52442 (12) | 0.36353 (11) | 0.0230 (7) | |
O4B | 0.2670 (4) | 0.25087 (14) | 0.59683 (12) | 0.0317 (8) | |
N1B | 0.8125 (4) | 0.52425 (15) | 0.31583 (13) | 0.0173 (8) | |
N2B | 0.6328 (5) | 0.47020 (15) | 0.39350 (13) | 0.0162 (8) | |
H2NB | 0.743 (6) | 0.466 (2) | 0.3966 (17) | 0.037 (16)* | |
N3B | 0.5289 (4) | 0.43565 (15) | 0.42449 (13) | 0.0167 (8) | |
C1B | 0.5841 (6) | 0.58351 (19) | 0.16043 (16) | 0.0262 (11) | |
C2B | 0.4256 (7) | 0.5602 (2) | 0.14837 (17) | 0.0306 (12) | |
H2BA | 0.336734 | 0.560183 | 0.174059 | 0.037* | |
C3B | 0.3972 (8) | 0.5369 (2) | 0.09889 (18) | 0.0402 (14) | |
H3BA | 0.288491 | 0.520856 | 0.090306 | 0.048* | |
C4B | 0.5270 (8) | 0.5370 (2) | 0.06179 (19) | 0.0421 (15) | |
H4BA | 0.506915 | 0.521500 | 0.027483 | 0.050* | |
C5B | 0.6854 (8) | 0.5596 (2) | 0.07435 (18) | 0.0411 (15) | |
H5BA | 0.773494 | 0.559106 | 0.048392 | 0.049* | |
C6B | 0.7201 (7) | 0.5830 (2) | 0.12396 (17) | 0.0288 (12) | |
C7B | 0.8927 (7) | 0.6065 (2) | 0.13842 (19) | 0.0436 (14) | |
H7BA | 0.972592 | 0.599935 | 0.109095 | 0.065* | |
H7BB | 0.934755 | 0.586470 | 0.170138 | 0.065* | |
H7BC | 0.883811 | 0.648494 | 0.145493 | 0.065* | |
C8B | 0.4962 (6) | 0.6076 (2) | 0.24845 (15) | 0.0219 (10) | |
H8BA | 0.472415 | 0.566859 | 0.259295 | 0.026* | |
H8BB | 0.388680 | 0.625069 | 0.234935 | 0.026* | |
C9B | 0.5618 (5) | 0.64225 (18) | 0.29482 (16) | 0.0189 (10) | |
C10B | 0.5292 (5) | 0.70184 (19) | 0.29708 (18) | 0.0233 (10) | |
H10B | 0.467486 | 0.719908 | 0.269115 | 0.028* | |
C11B | 0.5846 (6) | 0.73523 (19) | 0.33896 (17) | 0.0251 (11) | |
H11B | 0.561065 | 0.775948 | 0.339720 | 0.030* | |
C12B | 0.6743 (6) | 0.7096 (2) | 0.37989 (18) | 0.0262 (11) | |
H12B | 0.712485 | 0.732556 | 0.408898 | 0.031* | |
C13B | 0.7085 (5) | 0.65023 (18) | 0.37850 (16) | 0.0179 (10) | |
H13B | 0.769870 | 0.632444 | 0.406698 | 0.022* | |
C14B | 0.6535 (5) | 0.61669 (17) | 0.33608 (15) | 0.0150 (9) | |
C15B | 0.6889 (5) | 0.55231 (17) | 0.33677 (15) | 0.0146 (9) | |
C16B | 1.0620 (5) | 0.52601 (19) | 0.26879 (17) | 0.0265 (11) | |
H16D | 1.140421 | 0.550498 | 0.248146 | 0.040* | |
H16E | 1.014032 | 0.495489 | 0.245983 | 0.040* | |
H16F | 1.124637 | 0.507882 | 0.298122 | 0.040* | |
C17B | 0.5625 (6) | 0.51425 (18) | 0.36573 (16) | 0.0165 (9) | |
C18B | 0.6045 (6) | 0.39529 (17) | 0.45050 (15) | 0.0202 (10) | |
H18B | 0.723951 | 0.389250 | 0.445666 | 0.024* | |
C19B | 0.5101 (5) | 0.35823 (18) | 0.48761 (16) | 0.0184 (10) | |
C20B | 0.5908 (6) | 0.31021 (18) | 0.51064 (17) | 0.0260 (11) | |
H20B | 0.706140 | 0.301647 | 0.501444 | 0.031* | |
C21B | 0.5073 (6) | 0.27496 (19) | 0.54638 (17) | 0.0280 (11) | |
H21B | 0.564045 | 0.242095 | 0.561214 | 0.034* | |
C22B | 0.3384 (6) | 0.28772 (19) | 0.56077 (17) | 0.0242 (11) | |
C23B | 0.2560 (6) | 0.33560 (19) | 0.53859 (16) | 0.0230 (11) | |
H23B | 0.141060 | 0.344389 | 0.548127 | 0.028* | |
C24B | 0.3418 (6) | 0.37046 (18) | 0.50253 (16) | 0.0223 (10) | |
H24B | 0.285049 | 0.403319 | 0.487676 | 0.027* | |
C25B | 0.0980 (7) | 0.2648 (2) | 0.61572 (18) | 0.0385 (13) | |
H25D | 0.062675 | 0.235745 | 0.642073 | 0.058* | |
H25E | 0.017244 | 0.264353 | 0.586010 | 0.058* | |
H25F | 0.098807 | 0.303656 | 0.631938 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0168 (16) | 0.0271 (17) | 0.0170 (14) | −0.0021 (14) | 0.0002 (13) | 0.0029 (13) |
O2A | 0.0096 (16) | 0.0289 (17) | 0.0359 (18) | 0.0005 (14) | −0.0110 (14) | −0.0115 (14) |
O3A | 0.0121 (17) | 0.0238 (16) | 0.0239 (16) | 0.0015 (14) | −0.0024 (13) | −0.0022 (13) |
O4A | 0.0165 (18) | 0.0254 (17) | 0.0350 (17) | 0.0030 (15) | −0.0039 (14) | −0.0112 (14) |
N1A | 0.015 (2) | 0.023 (2) | 0.0234 (19) | 0.0005 (17) | 0.0000 (17) | −0.0075 (16) |
N2A | 0.009 (2) | 0.022 (2) | 0.0224 (19) | −0.0055 (17) | −0.0001 (17) | −0.0055 (16) |
N3A | 0.012 (2) | 0.0173 (19) | 0.0206 (18) | −0.0009 (16) | 0.0018 (16) | −0.0023 (16) |
C1A | 0.028 (3) | 0.013 (2) | 0.018 (2) | 0.002 (2) | 0.002 (2) | −0.0031 (18) |
C2A | 0.024 (3) | 0.026 (2) | 0.020 (2) | 0.002 (2) | 0.001 (2) | −0.0015 (19) |
C3A | 0.035 (3) | 0.027 (3) | 0.031 (3) | −0.001 (2) | 0.009 (3) | 0.004 (2) |
C4A | 0.055 (4) | 0.026 (3) | 0.025 (3) | 0.007 (3) | 0.008 (3) | 0.006 (2) |
C5A | 0.040 (3) | 0.024 (3) | 0.024 (2) | 0.011 (2) | −0.003 (2) | 0.000 (2) |
C6A | 0.028 (3) | 0.020 (2) | 0.020 (2) | 0.008 (2) | −0.002 (2) | −0.0007 (19) |
C7A | 0.023 (3) | 0.036 (3) | 0.031 (2) | 0.005 (2) | −0.007 (2) | 0.000 (2) |
C8A | 0.014 (2) | 0.029 (3) | 0.019 (2) | 0.002 (2) | −0.0037 (19) | −0.004 (2) |
C9A | 0.011 (2) | 0.019 (2) | 0.019 (2) | −0.0040 (19) | −0.0030 (18) | −0.0045 (18) |
C10A | 0.015 (2) | 0.021 (2) | 0.027 (2) | 0.001 (2) | −0.004 (2) | −0.007 (2) |
C11A | 0.019 (3) | 0.019 (2) | 0.031 (2) | 0.000 (2) | −0.005 (2) | 0.000 (2) |
C12A | 0.023 (3) | 0.027 (3) | 0.020 (2) | −0.008 (2) | −0.008 (2) | 0.005 (2) |
C13A | 0.015 (2) | 0.028 (3) | 0.017 (2) | −0.003 (2) | 0.0006 (19) | −0.0027 (19) |
C14A | 0.009 (2) | 0.020 (2) | 0.016 (2) | −0.0055 (18) | −0.0037 (17) | −0.0030 (18) |
C15A | 0.012 (2) | 0.021 (2) | 0.017 (2) | −0.0018 (19) | 0.0031 (19) | −0.0011 (18) |
C16A | 0.013 (3) | 0.046 (3) | 0.050 (3) | 0.007 (2) | −0.015 (2) | −0.016 (3) |
C17A | 0.016 (3) | 0.020 (2) | 0.015 (2) | −0.003 (2) | 0.0001 (18) | 0.0039 (18) |
C18A | 0.011 (2) | 0.023 (2) | 0.022 (2) | −0.005 (2) | −0.0076 (19) | 0.0033 (19) |
C19A | 0.012 (2) | 0.018 (2) | 0.021 (2) | 0.0007 (19) | 0.0021 (19) | 0.0004 (18) |
C20A | 0.016 (2) | 0.020 (2) | 0.023 (2) | 0.000 (2) | 0.0005 (19) | −0.0037 (19) |
C21A | 0.013 (2) | 0.024 (2) | 0.025 (2) | 0.005 (2) | −0.005 (2) | −0.001 (2) |
C22A | 0.019 (3) | 0.021 (2) | 0.022 (2) | −0.005 (2) | −0.001 (2) | −0.0031 (19) |
C23A | 0.014 (2) | 0.022 (2) | 0.031 (2) | 0.003 (2) | −0.002 (2) | −0.002 (2) |
C24A | 0.014 (2) | 0.024 (2) | 0.027 (2) | −0.001 (2) | 0.002 (2) | −0.004 (2) |
C25A | 0.029 (3) | 0.023 (2) | 0.030 (3) | 0.001 (2) | 0.002 (2) | −0.011 (2) |
O1B | 0.0268 (19) | 0.045 (2) | 0.0206 (16) | −0.0086 (17) | 0.0018 (15) | −0.0079 (15) |
O2B | 0.0186 (18) | 0.0185 (15) | 0.0313 (17) | 0.0018 (14) | 0.0127 (14) | 0.0030 (14) |
O3B | 0.0126 (17) | 0.0274 (17) | 0.0289 (16) | −0.0025 (14) | 0.0033 (14) | 0.0072 (14) |
O4B | 0.029 (2) | 0.0335 (19) | 0.0328 (18) | −0.0047 (16) | 0.0034 (15) | 0.0116 (16) |
N1B | 0.010 (2) | 0.0217 (19) | 0.0199 (18) | −0.0021 (17) | 0.0042 (15) | 0.0038 (16) |
N2B | 0.005 (2) | 0.022 (2) | 0.0218 (19) | −0.0023 (17) | 0.0002 (16) | 0.0020 (16) |
N3B | 0.011 (2) | 0.0199 (19) | 0.0192 (18) | −0.0034 (16) | −0.0014 (16) | −0.0002 (16) |
C1B | 0.035 (3) | 0.025 (2) | 0.019 (2) | −0.001 (2) | −0.006 (2) | −0.005 (2) |
C2B | 0.035 (3) | 0.031 (3) | 0.025 (2) | 0.003 (2) | −0.006 (2) | −0.001 (2) |
C3B | 0.060 (4) | 0.029 (3) | 0.032 (3) | −0.002 (3) | −0.017 (3) | 0.002 (2) |
C4B | 0.076 (5) | 0.027 (3) | 0.023 (3) | 0.000 (3) | −0.010 (3) | −0.007 (2) |
C5B | 0.069 (4) | 0.031 (3) | 0.024 (3) | 0.005 (3) | 0.011 (3) | 0.000 (2) |
C6B | 0.038 (3) | 0.027 (3) | 0.022 (2) | 0.005 (2) | 0.002 (2) | −0.001 (2) |
C7B | 0.042 (3) | 0.051 (3) | 0.038 (3) | 0.004 (3) | 0.008 (3) | −0.001 (3) |
C8B | 0.015 (2) | 0.031 (3) | 0.020 (2) | −0.004 (2) | 0.0042 (19) | 0.001 (2) |
C9B | 0.011 (2) | 0.025 (2) | 0.020 (2) | 0.004 (2) | 0.0000 (19) | 0.0018 (19) |
C10B | 0.009 (2) | 0.027 (2) | 0.033 (3) | 0.001 (2) | −0.002 (2) | 0.007 (2) |
C11B | 0.016 (3) | 0.017 (2) | 0.042 (3) | 0.004 (2) | 0.004 (2) | −0.004 (2) |
C12B | 0.018 (3) | 0.026 (3) | 0.034 (3) | −0.003 (2) | 0.005 (2) | −0.010 (2) |
C13B | 0.009 (2) | 0.024 (2) | 0.021 (2) | 0.0005 (19) | 0.0016 (19) | 0.0013 (19) |
C14B | 0.009 (2) | 0.017 (2) | 0.019 (2) | −0.0006 (18) | 0.0047 (18) | 0.0006 (18) |
C15B | 0.010 (2) | 0.019 (2) | 0.015 (2) | −0.0022 (19) | −0.0055 (18) | 0.0005 (18) |
C16B | 0.017 (3) | 0.028 (2) | 0.035 (3) | 0.008 (2) | 0.013 (2) | 0.004 (2) |
C17B | 0.012 (2) | 0.020 (2) | 0.018 (2) | 0.000 (2) | −0.0027 (18) | −0.0045 (18) |
C18B | 0.016 (2) | 0.021 (2) | 0.024 (2) | −0.003 (2) | −0.002 (2) | −0.0008 (19) |
C19B | 0.013 (2) | 0.018 (2) | 0.024 (2) | −0.0013 (19) | −0.0003 (19) | −0.0006 (19) |
C20B | 0.021 (3) | 0.027 (2) | 0.030 (3) | 0.004 (2) | −0.001 (2) | −0.001 (2) |
C21B | 0.027 (3) | 0.025 (3) | 0.032 (3) | 0.006 (2) | −0.002 (2) | 0.007 (2) |
C22B | 0.025 (3) | 0.023 (3) | 0.024 (2) | −0.007 (2) | 0.000 (2) | 0.005 (2) |
C23B | 0.013 (3) | 0.031 (3) | 0.025 (2) | −0.003 (2) | 0.001 (2) | 0.004 (2) |
C24B | 0.021 (3) | 0.021 (2) | 0.026 (2) | −0.002 (2) | −0.004 (2) | 0.004 (2) |
C25B | 0.035 (3) | 0.042 (3) | 0.038 (3) | −0.001 (3) | 0.014 (3) | 0.012 (2) |
O1A—C1A | 1.383 (5) | O1B—C1B | 1.378 (5) |
O1A—C8A | 1.443 (5) | O1B—C8B | 1.427 (5) |
O2A—N1A | 1.390 (4) | O2B—N1B | 1.395 (4) |
O2A—C16A | 1.443 (5) | O2B—C16B | 1.438 (5) |
O3A—C17A | 1.226 (5) | O3B—C17B | 1.231 (5) |
O4A—C22A | 1.360 (5) | O4B—C22B | 1.361 (5) |
O4A—C25A | 1.431 (5) | O4B—C25B | 1.439 (6) |
N1A—C15A | 1.276 (5) | N1B—C15B | 1.274 (5) |
N2A—C17A | 1.347 (5) | N2B—C17B | 1.345 (5) |
N2A—N3A | 1.395 (4) | N2B—N3B | 1.377 (5) |
N2A—H2NA | 0.90 (5) | N2B—H2NB | 0.87 (5) |
N3A—C18A | 1.279 (5) | N3B—C18B | 1.278 (5) |
C1A—C2A | 1.391 (6) | C1B—C2B | 1.381 (7) |
C1A—C6A | 1.401 (6) | C1B—C6B | 1.406 (6) |
C2A—C3A | 1.387 (6) | C2B—C3B | 1.377 (6) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.384 (7) | C3B—C4B | 1.380 (7) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.377 (7) | C4B—C5B | 1.377 (7) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.383 (6) | C5B—C6B | 1.390 (6) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.509 (6) | C6B—C7B | 1.495 (7) |
C7A—H7AA | 0.9800 | C7B—H7BA | 0.9800 |
C7A—H7AB | 0.9800 | C7B—H7BB | 0.9800 |
C7A—H7AC | 0.9800 | C7B—H7BC | 0.9800 |
C8A—C9A | 1.499 (5) | C8B—C9B | 1.504 (5) |
C8A—H8AA | 0.9900 | C8B—H8BA | 0.9900 |
C8A—H8AB | 0.9900 | C8B—H8BB | 0.9900 |
C9A—C10A | 1.396 (5) | C9B—C10B | 1.389 (6) |
C9A—C14A | 1.400 (5) | C9B—C14B | 1.393 (5) |
C10A—C11A | 1.381 (6) | C10B—C11B | 1.375 (6) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.376 (6) | C11B—C12B | 1.380 (6) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.388 (6) | C12B—C13B | 1.385 (6) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.397 (5) | C13B—C14B | 1.387 (5) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C15A | 1.493 (5) | C14B—C15B | 1.499 (5) |
C15A—C17A | 1.499 (6) | C15B—C17B | 1.506 (6) |
C16A—H16A | 0.9800 | C16B—H16D | 0.9800 |
C16A—H16B | 0.9800 | C16B—H16E | 0.9800 |
C16A—H16C | 0.9800 | C16B—H16F | 0.9800 |
C18A—C19A | 1.455 (5) | C18B—C19B | 1.463 (5) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C19A—C24A | 1.393 (6) | C19B—C24B | 1.395 (6) |
C19A—C20A | 1.394 (6) | C19B—C20B | 1.394 (6) |
C20A—C21A | 1.378 (5) | C20B—C21B | 1.375 (6) |
C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
C21A—C22A | 1.391 (5) | C21B—C22B | 1.398 (6) |
C21A—H21A | 0.9500 | C21B—H21B | 0.9500 |
C22A—C23A | 1.391 (6) | C22B—C23B | 1.389 (6) |
C23A—C24A | 1.377 (5) | C23B—C24B | 1.384 (6) |
C23A—H23A | 0.9500 | C23B—H23B | 0.9500 |
C24A—H24A | 0.9500 | C24B—H24B | 0.9500 |
C25A—H25A | 0.9800 | C25B—H25D | 0.9800 |
C25A—H25B | 0.9800 | C25B—H25E | 0.9800 |
C25A—H25C | 0.9800 | C25B—H25F | 0.9800 |
C1A—O1A—C8A | 116.9 (3) | C1B—O1B—C8B | 117.0 (3) |
N1A—O2A—C16A | 107.5 (3) | N1B—O2B—C16B | 107.3 (3) |
C22A—O4A—C25A | 117.5 (3) | C22B—O4B—C25B | 117.4 (4) |
C15A—N1A—O2A | 112.2 (3) | C15B—N1B—O2B | 111.7 (3) |
C17A—N2A—N3A | 120.3 (4) | C17B—N2B—N3B | 119.1 (4) |
C17A—N2A—H2NA | 120 (3) | C17B—N2B—H2NB | 122 (3) |
N3A—N2A—H2NA | 115 (3) | N3B—N2B—H2NB | 118 (3) |
C18A—N3A—N2A | 113.2 (3) | C18B—N3B—N2B | 115.8 (3) |
O1A—C1A—C2A | 124.2 (4) | O1B—C1B—C2B | 124.2 (4) |
O1A—C1A—C6A | 114.9 (4) | O1B—C1B—C6B | 113.9 (4) |
C2A—C1A—C6A | 120.9 (4) | C2B—C1B—C6B | 121.9 (4) |
C3A—C2A—C1A | 119.7 (4) | C3B—C2B—C1B | 119.6 (5) |
C3A—C2A—H2AA | 120.2 | C3B—C2B—H2BA | 120.2 |
C1A—C2A—H2AA | 120.2 | C1B—C2B—H2BA | 120.2 |
C4A—C3A—C2A | 119.8 (5) | C2B—C3B—C4B | 119.9 (5) |
C4A—C3A—H3AA | 120.1 | C2B—C3B—H3BA | 120.1 |
C2A—C3A—H3AA | 120.1 | C4B—C3B—H3BA | 120.1 |
C5A—C4A—C3A | 120.0 (4) | C5B—C4B—C3B | 120.2 (5) |
C5A—C4A—H4AA | 120.0 | C5B—C4B—H4BA | 119.9 |
C3A—C4A—H4AA | 120.0 | C3B—C4B—H4BA | 119.9 |
C4A—C5A—C6A | 121.6 (5) | C4B—C5B—C6B | 121.8 (5) |
C4A—C5A—H5AA | 119.2 | C4B—C5B—H5BA | 119.1 |
C6A—C5A—H5AA | 119.2 | C6B—C5B—H5BA | 119.1 |
C5A—C6A—C1A | 118.0 (4) | C5B—C6B—C1B | 116.6 (5) |
C5A—C6A—C7A | 122.1 (4) | C5B—C6B—C7B | 122.3 (5) |
C1A—C6A—C7A | 119.9 (4) | C1B—C6B—C7B | 121.2 (4) |
C6A—C7A—H7AA | 109.5 | C6B—C7B—H7BA | 109.5 |
C6A—C7A—H7AB | 109.5 | C6B—C7B—H7BB | 109.5 |
H7AA—C7A—H7AB | 109.5 | H7BA—C7B—H7BB | 109.5 |
C6A—C7A—H7AC | 109.5 | C6B—C7B—H7BC | 109.5 |
H7AA—C7A—H7AC | 109.5 | H7BA—C7B—H7BC | 109.5 |
H7AB—C7A—H7AC | 109.5 | H7BB—C7B—H7BC | 109.5 |
O1A—C8A—C9A | 108.9 (3) | O1B—C8B—C9B | 107.8 (3) |
O1A—C8A—H8AA | 109.9 | O1B—C8B—H8BA | 110.2 |
C9A—C8A—H8AA | 109.9 | C9B—C8B—H8BA | 110.2 |
O1A—C8A—H8AB | 109.9 | O1B—C8B—H8BB | 110.2 |
C9A—C8A—H8AB | 109.9 | C9B—C8B—H8BB | 110.2 |
H8AA—C8A—H8AB | 108.3 | H8BA—C8B—H8BB | 108.5 |
C10A—C9A—C14A | 118.5 (4) | C10B—C9B—C14B | 118.4 (4) |
C10A—C9A—C8A | 120.3 (4) | C10B—C9B—C8B | 119.2 (4) |
C14A—C9A—C8A | 121.2 (3) | C14B—C9B—C8B | 122.4 (4) |
C11A—C10A—C9A | 121.0 (4) | C11B—C10B—C9B | 121.3 (4) |
C11A—C10A—H10A | 119.5 | C11B—C10B—H10B | 119.3 |
C9A—C10A—H10A | 119.5 | C9B—C10B—H10B | 119.3 |
C12A—C11A—C10A | 120.3 (4) | C10B—C11B—C12B | 120.0 (4) |
C12A—C11A—H11A | 119.9 | C10B—C11B—H11B | 120.0 |
C10A—C11A—H11A | 119.9 | C12B—C11B—H11B | 120.0 |
C11A—C12A—C13A | 120.0 (4) | C11B—C12B—C13B | 119.7 (4) |
C11A—C12A—H12A | 120.0 | C11B—C12B—H12B | 120.1 |
C13A—C12A—H12A | 120.0 | C13B—C12B—H12B | 120.1 |
C12A—C13A—C14A | 120.1 (4) | C12B—C13B—C14B | 120.2 (4) |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 119.9 |
C14A—C13A—H13A | 120.0 | C14B—C13B—H13B | 119.9 |
C13A—C14A—C9A | 120.1 (4) | C13B—C14B—C9B | 120.3 (4) |
C13A—C14A—C15A | 118.4 (4) | C13B—C14B—C15B | 118.6 (4) |
C9A—C14A—C15A | 121.5 (3) | C9B—C14B—C15B | 121.1 (4) |
N1A—C15A—C14A | 126.4 (4) | N1B—C15B—C14B | 129.1 (4) |
N1A—C15A—C17A | 115.0 (4) | N1B—C15B—C17B | 114.0 (4) |
C14A—C15A—C17A | 118.6 (4) | C14B—C15B—C17B | 117.0 (4) |
O2A—C16A—H16A | 109.5 | O2B—C16B—H16D | 109.5 |
O2A—C16A—H16B | 109.5 | O2B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
O2A—C16A—H16C | 109.5 | O2B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
O3A—C17A—N2A | 124.9 (4) | O3B—C17B—N2B | 124.4 (4) |
O3A—C17A—C15A | 121.6 (4) | O3B—C17B—C15B | 120.7 (4) |
N2A—C17A—C15A | 113.5 (4) | N2B—C17B—C15B | 114.8 (4) |
N3A—C18A—C19A | 123.5 (4) | N3B—C18B—C19B | 121.1 (4) |
N3A—C18A—H18A | 118.2 | N3B—C18B—H18B | 119.5 |
C19A—C18A—H18A | 118.2 | C19B—C18B—H18B | 119.5 |
C24A—C19A—C20A | 118.5 (4) | C24B—C19B—C20B | 118.1 (4) |
C24A—C19A—C18A | 118.6 (4) | C24B—C19B—C18B | 122.1 (4) |
C20A—C19A—C18A | 122.8 (4) | C20B—C19B—C18B | 119.8 (4) |
C21A—C20A—C19A | 120.5 (4) | C21B—C20B—C19B | 121.5 (4) |
C21A—C20A—H20A | 119.7 | C21B—C20B—H20B | 119.2 |
C19A—C20A—H20A | 119.7 | C19B—C20B—H20B | 119.2 |
C20A—C21A—C22A | 120.1 (4) | C20B—C21B—C22B | 119.7 (4) |
C20A—C21A—H21A | 119.9 | C20B—C21B—H21B | 120.2 |
C22A—C21A—H21A | 119.9 | C22B—C21B—H21B | 120.2 |
O4A—C22A—C21A | 115.3 (4) | O4B—C22B—C23B | 124.7 (4) |
O4A—C22A—C23A | 124.7 (4) | O4B—C22B—C21B | 115.5 (4) |
C21A—C22A—C23A | 120.0 (4) | C23B—C22B—C21B | 119.8 (4) |
C24A—C23A—C22A | 119.3 (4) | C24B—C23B—C22B | 119.8 (4) |
C24A—C23A—H23A | 120.4 | C24B—C23B—H23B | 120.1 |
C22A—C23A—H23A | 120.4 | C22B—C23B—H23B | 120.1 |
C23A—C24A—C19A | 121.5 (4) | C23B—C24B—C19B | 121.2 (4) |
C23A—C24A—H24A | 119.3 | C23B—C24B—H24B | 119.4 |
C19A—C24A—H24A | 119.3 | C19B—C24B—H24B | 119.4 |
O4A—C25A—H25A | 109.5 | O4B—C25B—H25D | 109.5 |
O4A—C25A—H25B | 109.5 | O4B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
O4A—C25A—H25C | 109.5 | O4B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
C16A—O2A—N1A—C15A | −179.4 (3) | C16B—O2B—N1B—C15B | 178.3 (3) |
C17A—N2A—N3A—C18A | 173.2 (3) | C17B—N2B—N3B—C18B | −178.8 (4) |
C8A—O1A—C1A—C2A | 2.0 (5) | C8B—O1B—C1B—C2B | 3.2 (6) |
C8A—O1A—C1A—C6A | −176.9 (3) | C8B—O1B—C1B—C6B | −176.4 (4) |
O1A—C1A—C2A—C3A | −177.7 (4) | O1B—C1B—C2B—C3B | 178.9 (4) |
C6A—C1A—C2A—C3A | 1.2 (6) | C6B—C1B—C2B—C3B | −1.6 (7) |
C1A—C2A—C3A—C4A | −0.6 (6) | C1B—C2B—C3B—C4B | 0.1 (7) |
C2A—C3A—C4A—C5A | 0.1 (7) | C2B—C3B—C4B—C5B | 0.9 (7) |
C3A—C4A—C5A—C6A | −0.2 (7) | C3B—C4B—C5B—C6B | −0.3 (8) |
C4A—C5A—C6A—C1A | 0.7 (6) | C4B—C5B—C6B—C1B | −1.1 (7) |
C4A—C5A—C6A—C7A | 179.4 (4) | C4B—C5B—C6B—C7B | 178.7 (5) |
O1A—C1A—C6A—C5A | 177.7 (3) | O1B—C1B—C6B—C5B | −178.3 (4) |
C2A—C1A—C6A—C5A | −1.2 (6) | C2B—C1B—C6B—C5B | 2.1 (7) |
O1A—C1A—C6A—C7A | −1.0 (6) | O1B—C1B—C6B—C7B | 1.9 (6) |
C2A—C1A—C6A—C7A | −179.9 (4) | C2B—C1B—C6B—C7B | −177.7 (4) |
C1A—O1A—C8A—C9A | 174.5 (3) | C1B—O1B—C8B—C9B | −174.6 (3) |
O1A—C8A—C9A—C10A | −99.7 (4) | O1B—C8B—C9B—C10B | 89.5 (5) |
O1A—C8A—C9A—C14A | 82.3 (4) | O1B—C8B—C9B—C14B | −91.0 (5) |
C14A—C9A—C10A—C11A | 0.7 (6) | C14B—C9B—C10B—C11B | −0.4 (6) |
C8A—C9A—C10A—C11A | −177.3 (4) | C8B—C9B—C10B—C11B | 179.2 (4) |
C9A—C10A—C11A—C12A | −1.1 (6) | C9B—C10B—C11B—C12B | −0.1 (7) |
C10A—C11A—C12A—C13A | 0.2 (6) | C10B—C11B—C12B—C13B | 0.1 (7) |
C11A—C12A—C13A—C14A | 1.0 (6) | C11B—C12B—C13B—C14B | 0.3 (6) |
C12A—C13A—C14A—C9A | −1.3 (6) | C12B—C13B—C14B—C9B | −0.7 (6) |
C12A—C13A—C14A—C15A | 175.8 (4) | C12B—C13B—C14B—C15B | −178.4 (4) |
C10A—C9A—C14A—C13A | 0.4 (6) | C10B—C9B—C14B—C13B | 0.8 (6) |
C8A—C9A—C14A—C13A | 178.5 (4) | C8B—C9B—C14B—C13B | −178.8 (4) |
C10A—C9A—C14A—C15A | −176.6 (4) | C10B—C9B—C14B—C15B | 178.4 (4) |
C8A—C9A—C14A—C15A | 1.5 (6) | C8B—C9B—C14B—C15B | −1.2 (6) |
O2A—N1A—C15A—C14A | 0.7 (6) | O2B—N1B—C15B—C14B | 0.2 (6) |
O2A—N1A—C15A—C17A | 179.3 (3) | O2B—N1B—C15B—C17B | 179.9 (3) |
C13A—C14A—C15A—N1A | 90.4 (5) | C13B—C14B—C15B—N1B | −95.4 (5) |
C9A—C14A—C15A—N1A | −92.5 (5) | C9B—C14B—C15B—N1B | 87.0 (5) |
C13A—C14A—C15A—C17A | −88.2 (5) | C13B—C14B—C15B—C17B | 84.9 (5) |
C9A—C14A—C15A—C17A | 88.9 (5) | C9B—C14B—C15B—C17B | −92.7 (5) |
N3A—N2A—C17A—O3A | 7.3 (6) | N3B—N2B—C17B—O3B | −4.2 (6) |
N3A—N2A—C17A—C15A | −174.4 (3) | N3B—N2B—C17B—C15B | 175.2 (3) |
N1A—C15A—C17A—O3A | 147.3 (4) | N1B—C15B—C17B—O3B | −141.2 (4) |
C14A—C15A—C17A—O3A | −33.9 (6) | C14B—C15B—C17B—O3B | 38.6 (6) |
N1A—C15A—C17A—N2A | −31.1 (5) | N1B—C15B—C17B—N2B | 39.4 (5) |
C14A—C15A—C17A—N2A | 147.7 (4) | C14B—C15B—C17B—N2B | −140.9 (4) |
N2A—N3A—C18A—C19A | −173.6 (3) | N2B—N3B—C18B—C19B | 175.8 (3) |
N3A—C18A—C19A—C24A | −169.1 (4) | N3B—C18B—C19B—C24B | −10.0 (6) |
N3A—C18A—C19A—C20A | 15.1 (6) | N3B—C18B—C19B—C20B | 172.3 (4) |
C24A—C19A—C20A—C21A | 0.7 (6) | C24B—C19B—C20B—C21B | 1.2 (6) |
C18A—C19A—C20A—C21A | 176.5 (4) | C18B—C19B—C20B—C21B | 178.9 (4) |
C19A—C20A—C21A—C22A | 0.1 (6) | C19B—C20B—C21B—C22B | −1.0 (7) |
C25A—O4A—C22A—C21A | 179.5 (4) | C25B—O4B—C22B—C23B | −4.1 (6) |
C25A—O4A—C22A—C23A | 0.1 (6) | C25B—O4B—C22B—C21B | 175.6 (4) |
C20A—C21A—C22A—O4A | −179.8 (4) | C20B—C21B—C22B—O4B | −179.2 (4) |
C20A—C21A—C22A—C23A | −0.5 (6) | C20B—C21B—C22B—C23B | 0.5 (6) |
O4A—C22A—C23A—C24A | 179.4 (4) | O4B—C22B—C23B—C24B | 179.4 (4) |
C21A—C22A—C23A—C24A | 0.1 (6) | C21B—C22B—C23B—C24B | −0.2 (6) |
C22A—C23A—C24A—C19A | 0.7 (6) | C22B—C23B—C24B—C19B | 0.4 (6) |
C20A—C19A—C24A—C23A | −1.1 (6) | C20B—C19B—C24B—C23B | −0.9 (6) |
C18A—C19A—C24A—C23A | −177.1 (4) | C18B—C19B—C24B—C23B | −178.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···O3B | 0.90 (5) | 2.04 (5) | 2.797 (5) | 141 (4) |
N2A—H2NA···N3B | 0.90 (5) | 2.54 (5) | 3.331 (5) | 147 (4) |
C16A—H16B···O3Ai | 0.98 | 2.51 | 3.353 (6) | 144 |
C18A—H18A···N3B | 0.95 | 2.60 | 3.494 (5) | 158 |
N2B—H2NB···O3Ai | 0.87 (5) | 2.50 (5) | 2.995 (5) | 117 (4) |
N2B—H2NB···N3Ai | 0.87 (5) | 2.29 (5) | 3.155 (5) | 172 (4) |
Symmetry code: (i) x+1, y, z. |
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