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The asymmetric unit of O,O′-dimethyl [(2,3,4,5,6-penta­fluoro­phenyl)­hydrazin­yl]phospho­nate, C8H8F5N2O3P, is composed of two symmetry-independent mol­ecules with significant differences in the orientations of the C6F5 and OMe groups. In the crystal structure, a one-dimensional assembly is mediated from classical N—H...O hydrogen bonds, which includes R22(8), D(2) and some higher-order graph-set motifs. By also considering weak C—H...O=P and C—H...O—C inter­molecular inter­actions, a two-dimensional network extends along the ab plane. The strengths of the hydrogen bonds were evaluated using quantum chemical calculations with the GAUSSIAN09 software package at the B3LYP/6-311G(d,p) level of theory. The LP(O) to σ*(NH) and σ*(CH) charge-transfer inter­actions were examined according to second-order perturbation theory in natural bond orbital (NBO) methodology. The hydrogen-bonded clusters of mol­ecules, including N—H...O and C—H...O inter­actions, were constructed as input files for the calculations and the strengths of the hydrogen bonds are as follows: N—H...O [R22(8)] > N—H...O [D(2)] > C—H...O. The decomposed fingerprint plots show that the contribution portions of the F...H/H...F contacts in both mol­ecules are the largest.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619011641/qs3086sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011641/qs3086Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619011641/qs3086sup3.pdf
Hydrogen-bond geometry details, NBO analysis results and NMR spectrum

CCDC reference: 1948351

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).

O,O'-Dimethyl [(2,3,4,5,6-pentafluorophenylhydrazinyl]phosphonate top
Crystal data top
C8H8F5N2O3PF(000) = 1232
Mr = 306.13Dx = 1.773 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.5273 (2) ÅCell parameters from 4434 reflections
b = 10.3266 (3) Åθ = 3.4–32.6°
c = 21.1193 (5) ŵ = 0.31 mm1
β = 92.647 (2)°T = 173 K
V = 2293.46 (10) Å3Prism, light yellow
Z = 80.34 × 0.14 × 0.12 mm
Data collection top
Rigaku Oxford diffraction
diffractometer
7628 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source5724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 16.0416 pixels mm-1θmax = 32.8°, θmin = 3.3°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1513
Tmin = 0.790, Tmax = 1.000l = 3131
18096 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.6442P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7628 reflectionsΔρmax = 0.50 e Å3
363 parametersΔρmin = 0.49 e Å3
0 restraints
Special details top

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. The crystal structure of (I) was determined by mounting a single crystal of the compound on a polymer loop and data were measured with a Rigaku-Oxford Diffraction Eos Gemini CCD X-ray diffractometer using CrysalisPro software (Rigaku, Oxford Diffraction, 2015) and equipped with graphite-monochromated Mo-Kα (λ = 0.71073 Å) radiation at 173 (2) K. The structure was solved by direct methods and refined using full-matrix least-squares based on F2 using ShelXL-2018 (Sheldrick, 2015). In this structure, all non-hydrogen atoms were refined anisotropically.

An absorption correction was performed using CrysAlisRED (Rigaku, Oxford Diffraction, 2014) and all calculations were performed using SHELXTL2018 (Sheldrick, 2015). The structure was checked using PLATON (Spek, 2009). The crystal data and the details of the X-ray analysis are given in Table 1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P1A0.29657 (4)0.48507 (4)0.52274 (2)0.02069 (9)
F1A0.48805 (11)0.85269 (10)0.67135 (5)0.0340 (2)
F2A0.56022 (12)0.84382 (12)0.79508 (5)0.0403 (3)
F3A0.49519 (12)0.63884 (13)0.86735 (5)0.0414 (3)
F4A0.35451 (12)0.44170 (12)0.81350 (5)0.0416 (3)
F5A0.28185 (11)0.44920 (11)0.69095 (5)0.0363 (3)
O1A0.36850 (11)0.39164 (12)0.48608 (6)0.0269 (3)
O2A0.22388 (11)0.59143 (13)0.48207 (5)0.0264 (3)
O3A0.18808 (12)0.41813 (13)0.55819 (6)0.0329 (3)
N1A0.39446 (13)0.55359 (14)0.57569 (6)0.0219 (3)
N2A0.34352 (13)0.65722 (14)0.61198 (6)0.0214 (3)
C1A0.38299 (15)0.65152 (16)0.67655 (7)0.0213 (3)
C2A0.45274 (16)0.75067 (16)0.70596 (8)0.0236 (3)
C3A0.48964 (17)0.74787 (17)0.76964 (8)0.0267 (3)
C4A0.45659 (17)0.64409 (19)0.80618 (8)0.0290 (4)
C5A0.38668 (17)0.54401 (18)0.77878 (8)0.0280 (3)
C6A0.35049 (16)0.54848 (17)0.71505 (8)0.0252 (3)
C7A0.07731 (17)0.4811 (2)0.58031 (10)0.0393 (5)
H7AA0.0493790.5483660.5500490.059*
H7AB0.0975770.5206130.6217410.059*
H7AC0.0091680.4173430.5842900.059*
C8A0.2887 (2)0.65158 (19)0.43065 (8)0.0331 (4)
H8AA0.3054750.5864050.3983540.050*
H8AB0.3694240.6886280.4470460.050*
H8AC0.2352100.7203770.4117890.050*
P1B0.29165 (4)0.01756 (4)0.51345 (2)0.01901 (9)
F1B0.28927 (11)0.05031 (10)0.33505 (5)0.0363 (3)
F2B0.18421 (11)0.02633 (11)0.21976 (5)0.0366 (3)
F3B0.04720 (11)0.18652 (12)0.18421 (5)0.0395 (3)
F4B0.02299 (12)0.38349 (11)0.26905 (6)0.0416 (3)
F5B0.13675 (11)0.36714 (10)0.38549 (5)0.0340 (2)
O1B0.38949 (11)0.11079 (12)0.53644 (6)0.0250 (2)
O2B0.25057 (11)0.08045 (13)0.56556 (6)0.0280 (3)
O3B0.16148 (10)0.07478 (12)0.48915 (5)0.0250 (2)
N1B0.34036 (13)0.05876 (14)0.45123 (6)0.0227 (3)
N2B0.26314 (14)0.16082 (14)0.42822 (6)0.0232 (3)
C1B0.21704 (14)0.15938 (15)0.36578 (7)0.0193 (3)
C2B0.22656 (15)0.05979 (16)0.32162 (8)0.0231 (3)
C3B0.17144 (16)0.07106 (17)0.26100 (8)0.0247 (3)
C4B0.10291 (16)0.17953 (18)0.24254 (8)0.0264 (3)
C5B0.09053 (16)0.27815 (17)0.28519 (8)0.0261 (3)
C6B0.14768 (15)0.26777 (16)0.34484 (8)0.0228 (3)
C7B0.07676 (16)0.13699 (18)0.53186 (9)0.0307 (4)
H7BA0.0054880.1763330.5073280.046*
H7BB0.0442570.0724900.5610520.046*
H7BC0.1231740.2042690.5560960.046*
C8B0.34889 (19)0.1448 (2)0.60413 (9)0.0347 (4)
H8BA0.4112730.1831510.5766470.052*
H8BB0.3912960.0816750.6325880.052*
H8BC0.3106200.2130420.6292520.052*
H2A0.3656 (19)0.731 (2)0.5941 (10)0.028 (5)*
H1A0.463 (2)0.565 (2)0.5635 (10)0.029 (5)*
H1B0.418 (2)0.072 (2)0.4499 (10)0.033 (6)*
H2B0.282 (2)0.232 (2)0.4424 (11)0.038 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P1A0.01861 (17)0.0234 (2)0.02021 (18)0.00111 (15)0.00272 (14)0.00122 (15)
F1A0.0461 (6)0.0287 (5)0.0269 (5)0.0106 (5)0.0019 (5)0.0053 (4)
F2A0.0526 (7)0.0401 (6)0.0275 (5)0.0127 (6)0.0043 (5)0.0068 (5)
F3A0.0534 (7)0.0541 (8)0.0164 (4)0.0055 (6)0.0030 (5)0.0025 (5)
F4A0.0614 (8)0.0378 (6)0.0258 (5)0.0077 (6)0.0045 (5)0.0114 (5)
F5A0.0484 (6)0.0313 (6)0.0288 (5)0.0143 (5)0.0021 (5)0.0027 (5)
O1A0.0266 (6)0.0257 (6)0.0287 (6)0.0015 (5)0.0036 (5)0.0061 (5)
O2A0.0245 (5)0.0335 (7)0.0211 (5)0.0041 (5)0.0000 (4)0.0008 (5)
O3A0.0267 (6)0.0333 (7)0.0395 (7)0.0016 (5)0.0105 (5)0.0034 (6)
N1A0.0193 (6)0.0259 (7)0.0206 (6)0.0007 (5)0.0025 (5)0.0018 (5)
N2A0.0260 (6)0.0212 (6)0.0168 (6)0.0022 (5)0.0005 (5)0.0011 (5)
C1A0.0224 (7)0.0225 (7)0.0190 (6)0.0024 (6)0.0017 (6)0.0002 (6)
C2A0.0267 (7)0.0236 (8)0.0207 (7)0.0005 (6)0.0022 (6)0.0015 (6)
C3A0.0302 (8)0.0285 (8)0.0214 (7)0.0015 (7)0.0000 (6)0.0037 (6)
C4A0.0334 (8)0.0365 (10)0.0172 (7)0.0040 (7)0.0015 (6)0.0009 (7)
C5A0.0344 (9)0.0291 (9)0.0207 (7)0.0001 (7)0.0046 (7)0.0055 (7)
C6A0.0306 (8)0.0240 (8)0.0212 (7)0.0017 (7)0.0020 (6)0.0002 (6)
C7A0.0248 (8)0.0548 (13)0.0390 (10)0.0008 (9)0.0087 (8)0.0026 (10)
C8A0.0444 (10)0.0303 (9)0.0246 (8)0.0011 (8)0.0026 (7)0.0042 (7)
P1B0.01821 (17)0.01989 (19)0.01877 (17)0.00132 (14)0.00110 (14)0.00191 (15)
F1B0.0501 (7)0.0230 (5)0.0350 (6)0.0149 (5)0.0044 (5)0.0020 (4)
F2B0.0459 (6)0.0337 (6)0.0298 (5)0.0048 (5)0.0009 (5)0.0123 (5)
F3B0.0472 (6)0.0488 (7)0.0211 (5)0.0075 (6)0.0113 (5)0.0007 (5)
F4B0.0527 (7)0.0335 (6)0.0373 (6)0.0189 (5)0.0123 (5)0.0040 (5)
F5B0.0453 (6)0.0246 (5)0.0312 (5)0.0129 (5)0.0075 (5)0.0066 (4)
O1B0.0232 (5)0.0242 (6)0.0272 (6)0.0017 (5)0.0024 (4)0.0063 (5)
O2B0.0273 (6)0.0310 (6)0.0256 (6)0.0014 (5)0.0010 (5)0.0048 (5)
O3B0.0195 (5)0.0287 (6)0.0267 (6)0.0026 (5)0.0010 (4)0.0014 (5)
N1B0.0181 (6)0.0257 (7)0.0240 (6)0.0035 (5)0.0015 (5)0.0072 (5)
N2B0.0294 (7)0.0189 (6)0.0207 (6)0.0028 (5)0.0054 (5)0.0009 (5)
C1B0.0184 (6)0.0189 (7)0.0207 (7)0.0009 (5)0.0008 (5)0.0032 (6)
C2B0.0250 (7)0.0185 (7)0.0259 (7)0.0022 (6)0.0004 (6)0.0010 (6)
C3B0.0275 (7)0.0241 (8)0.0228 (7)0.0005 (6)0.0023 (6)0.0042 (6)
C4B0.0284 (8)0.0307 (9)0.0197 (7)0.0004 (7)0.0019 (6)0.0023 (6)
C5B0.0284 (8)0.0225 (8)0.0269 (8)0.0051 (6)0.0032 (6)0.0058 (6)
C6B0.0262 (7)0.0186 (7)0.0235 (7)0.0016 (6)0.0002 (6)0.0013 (6)
C7B0.0237 (8)0.0287 (9)0.0402 (10)0.0012 (7)0.0059 (7)0.0052 (8)
C8B0.0423 (10)0.0317 (9)0.0292 (9)0.0027 (8)0.0069 (8)0.0063 (8)
Geometric parameters (Å, º) top
P1A—O1A1.4690 (12)P1B—O1B1.4756 (12)
P1A—O2A1.5712 (13)P1B—O2B1.5706 (12)
P1A—O3A1.5562 (13)P1B—O3B1.5573 (12)
P1A—N1A1.6452 (15)P1B—N1B1.6349 (14)
F1A—C2A1.3444 (19)F1B—C2B1.3386 (19)
F2A—C3A1.336 (2)F2B—C3B1.3413 (19)
F3A—C4A1.3375 (19)F3B—C4B1.3415 (19)
F4A—C5A1.338 (2)F4B—C5B1.3352 (19)
F5A—C6A1.341 (2)F5B—C6B1.3462 (18)
O2A—C8A1.449 (2)O2B—C8B1.449 (2)
O3A—C7A1.432 (2)O3B—C7B1.448 (2)
N1A—N2A1.4346 (19)N1B—N2B1.4040 (19)
N1A—H1A0.79 (2)N1B—H1B0.83 (2)
N2A—C1A1.408 (2)N2B—C1B1.384 (2)
N2A—H2A0.88 (2)N2B—H2B0.82 (2)
C1A—C2A1.390 (2)C1B—C2B1.395 (2)
C1A—C6A1.392 (2)C1B—C6B1.397 (2)
C2A—C3A1.383 (2)C2B—C3B1.386 (2)
C3A—C4A1.375 (3)C3B—C4B1.379 (2)
C4A—C5A1.380 (3)C4B—C5B1.370 (2)
C5A—C6A1.382 (2)C5B—C6B1.375 (2)
C7A—H7AA0.9800C7B—H7BA0.9800
C7A—H7AB0.9800C7B—H7BB0.9800
C7A—H7AC0.9800C7B—H7BC0.9800
C8A—H8AA0.9800C8B—H8BA0.9800
C8A—H8AB0.9800C8B—H8BB0.9800
C8A—H8AC0.9800C8B—H8BC0.9800
O1A—P1A—O2A114.89 (7)O1B—P1B—O2B113.61 (7)
O1A—P1A—O3A111.68 (8)O1B—P1B—O3B116.81 (7)
O1A—P1A—N1A108.59 (7)O1B—P1B—N1B109.81 (7)
O2A—P1A—N1A110.17 (7)O2B—P1B—N1B111.06 (7)
O3A—P1A—O2A102.93 (7)O3B—P1B—O2B102.05 (6)
O3A—P1A—N1A108.34 (7)O3B—P1B—N1B102.82 (7)
C8A—O2A—P1A118.35 (11)C8B—O2B—P1B118.48 (11)
C7A—O3A—P1A125.59 (13)C7B—O3B—P1B121.41 (11)
P1A—N1A—H1A113.5 (15)P1B—N1B—H1B116.8 (15)
N2A—N1A—P1A116.49 (10)N2B—N1B—P1B116.23 (11)
N2A—N1A—H1A115.7 (16)N2B—N1B—H1B115.0 (16)
N1A—N2A—H2A107.5 (13)N1B—N2B—H2B114.7 (17)
C1A—N2A—N1A112.66 (12)C1B—N2B—N1B119.57 (13)
C1A—N2A—H2A112.2 (14)C1B—N2B—H2B115.5 (17)
C2A—C1A—N2A121.89 (14)N2B—C1B—C2B127.74 (14)
C2A—C1A—C6A116.19 (14)N2B—C1B—C6B116.62 (14)
C6A—C1A—N2A121.89 (15)C2B—C1B—C6B115.57 (14)
F1A—C2A—C1A119.20 (14)F1B—C2B—C1B122.31 (14)
F1A—C2A—C3A118.22 (15)F1B—C2B—C3B116.64 (15)
C3A—C2A—C1A122.56 (15)C3B—C2B—C1B121.05 (15)
F2A—C3A—C2A120.10 (15)F2B—C3B—C2B119.13 (15)
F2A—C3A—C4A120.19 (15)F2B—C3B—C4B119.49 (15)
C4A—C3A—C2A119.68 (16)C4B—C3B—C2B121.38 (15)
F3A—C4A—C3A120.02 (17)F3B—C4B—C3B120.27 (16)
F3A—C4A—C5A120.46 (16)F3B—C4B—C5B120.87 (16)
C3A—C4A—C5A119.49 (15)C5B—C4B—C3B118.84 (15)
F4A—C5A—C4A120.32 (15)F4B—C5B—C4B120.23 (15)
F4A—C5A—C6A119.63 (16)F4B—C5B—C6B120.18 (16)
C4A—C5A—C6A120.05 (16)C4B—C5B—C6B119.59 (15)
F5A—C6A—C1A120.37 (14)F5B—C6B—C1B117.88 (14)
F5A—C6A—C5A117.61 (15)F5B—C6B—C5B118.57 (14)
C5A—C6A—C1A122.03 (16)C5B—C6B—C1B123.55 (15)
O3A—C7A—H7AA109.5O3B—C7B—H7BA109.5
O3A—C7A—H7AB109.5O3B—C7B—H7BB109.5
O3A—C7A—H7AC109.5O3B—C7B—H7BC109.5
H7AA—C7A—H7AB109.5H7BA—C7B—H7BB109.5
H7AA—C7A—H7AC109.5H7BA—C7B—H7BC109.5
H7AB—C7A—H7AC109.5H7BB—C7B—H7BC109.5
O2A—C8A—H8AA109.5O2B—C8B—H8BA109.5
O2A—C8A—H8AB109.5O2B—C8B—H8BB109.5
O2A—C8A—H8AC109.5O2B—C8B—H8BC109.5
H8AA—C8A—H8AB109.5H8BA—C8B—H8BB109.5
H8AA—C8A—H8AC109.5H8BA—C8B—H8BC109.5
H8AB—C8A—H8AC109.5H8BB—C8B—H8BC109.5
P1A—N1A—N2A—C1A138.22 (12)P1B—N1B—N2B—C1B123.74 (14)
F1A—C2A—C3A—F2A1.1 (2)F1B—C2B—C3B—F2B0.4 (2)
F1A—C2A—C3A—C4A179.12 (15)F1B—C2B—C3B—C4B178.92 (15)
F2A—C3A—C4A—F3A0.1 (3)F2B—C3B—C4B—F3B1.4 (2)
F2A—C3A—C4A—C5A178.18 (16)F2B—C3B—C4B—C5B179.91 (15)
F3A—C4A—C5A—F4A1.4 (3)F3B—C4B—C5B—F4B0.4 (3)
F3A—C4A—C5A—C6A178.03 (16)F3B—C4B—C5B—C6B179.38 (16)
F4A—C5A—C6A—F5A1.1 (2)F4B—C5B—C6B—F5B1.8 (2)
F4A—C5A—C6A—C1A179.01 (15)F4B—C5B—C6B—C1B178.31 (15)
O1A—P1A—O2A—C8A42.82 (15)O1B—P1B—O2B—C8B47.26 (15)
O1A—P1A—O3A—C7A158.36 (15)O1B—P1B—O3B—C7B67.71 (14)
O1A—P1A—N1A—N2A174.10 (11)O1B—P1B—N1B—N2B173.23 (11)
O2A—P1A—O3A—C7A34.58 (17)O2B—P1B—O3B—C7B56.81 (14)
O2A—P1A—N1A—N2A47.47 (12)O2B—P1B—N1B—N2B46.73 (14)
O3A—P1A—O2A—C8A164.45 (13)O3B—P1B—O2B—C8B173.90 (13)
O3A—P1A—N1A—N2A64.43 (13)O3B—P1B—N1B—N2B61.76 (13)
N1A—P1A—O2A—C8A80.19 (13)N1B—P1B—O2B—C8B77.12 (14)
N1A—P1A—O3A—C7A82.10 (17)N1B—P1B—O3B—C7B171.99 (13)
N1A—N2A—C1A—C2A119.18 (16)N1B—N2B—C1B—C2B7.1 (2)
N1A—N2A—C1A—C6A63.17 (19)N1B—N2B—C1B—C6B176.00 (14)
N2A—C1A—C2A—F1A2.7 (2)N2B—C1B—C2B—F1B2.6 (3)
N2A—C1A—C2A—C3A178.46 (15)N2B—C1B—C2B—C3B177.79 (15)
N2A—C1A—C6A—F5A1.4 (2)N2B—C1B—C6B—F5B3.4 (2)
N2A—C1A—C6A—C5A178.52 (15)N2B—C1B—C6B—C5B176.71 (15)
C1A—C2A—C3A—F2A177.80 (15)C1B—C2B—C3B—F2B179.18 (14)
C1A—C2A—C3A—C4A0.3 (3)C1B—C2B—C3B—C4B1.5 (2)
C2A—C1A—C6A—F5A179.15 (15)C2B—C1B—C6B—F5B179.36 (14)
C2A—C1A—C6A—C5A0.7 (2)C2B—C1B—C6B—C5B0.5 (2)
C2A—C3A—C4A—F3A177.98 (16)C2B—C3B—C4B—F3B177.98 (15)
C2A—C3A—C4A—C5A0.1 (3)C2B—C3B—C4B—C5B0.6 (3)
C3A—C4A—C5A—F4A179.46 (16)C3B—C4B—C5B—F4B178.90 (15)
C3A—C4A—C5A—C6A0.1 (3)C3B—C4B—C5B—C6B0.8 (3)
C4A—C5A—C6A—F5A179.50 (16)C4B—C5B—C6B—F5B178.47 (15)
C4A—C5A—C6A—C1A0.4 (3)C4B—C5B—C6B—C1B1.4 (3)
C6A—C1A—C2A—F1A179.51 (14)C6B—C1B—C2B—F1B179.53 (14)
C6A—C1A—C2A—C3A0.7 (2)C6B—C1B—C2B—C3B0.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AB···F5A0.982.493.121 (2)122
C7A—H7AC···O2Ai0.982.773.459 (2)128
C8A—H8AB···O1Bii0.982.803.452 (2)124
C7B—H7BB···F4Aiii0.982.813.411 (2)120
N2A—H2A···O1Bii0.88 (2)2.06 (2)2.9308 (18)167.3 (19)
N1A—H1A···O1Aiv0.79 (2)2.14 (2)2.9238 (18)169 (2)
N1B—H1B···O1Bv0.83 (2)2.07 (2)2.8942 (18)170 (2)
N2B—H2B···O1A0.82 (2)2.08 (2)2.8774 (19)167 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x+1/2, y1/2, z+3/2; (iv) x+1, y+1, z+1; (v) x+1, y, z+1.
NBO analysis results for C—H···O intermolecular interactions in clusters IV and VI by the B3LYP/6-311g(d,p) method top
DonorOccu. No.E (a.u.)AcceptorOccu. No.E (a.u.)E(2) (kcal mol-1)
LP(1) O2A1.96384–0.632730.31
σ*(C7A—H7AC)0.011780.39569
LP(2) O2A1.92590–0.345260.73
LP(2) O1B1.86703–0.32406σ*(C8A—H8AB)0.014160.379750.57
 

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