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The asymmetric unit of the title compound, 2C15H9F6N3O·H2O, contains two independent Schiff base mol­ecules and one water mol­ecule. Both Schiff base mol­ecules exist in an E configuration with respect to the C=N double bonds and the dihedral angles between the benzene and the pyridine rings in the two mol­ecules are 17.53 (12) and 20.62 (12)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H...O and C—H...O hydrogen bonds into infinite one-dimensional chains along the a axis. In addition, inter­molecular O—H...N, O—H...F, C—H...F and C—H...O hydrogen bonds further link these chains into a three-dimensional network. Weak π–π inter­actions with centroid–centroid distances in the range 3.6495 (17)–3.7092 (16) Å are also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810025493/lh5074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810025493/lh5074Isup2.hkl
Contains datablock I

CCDC reference: 788323

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.162
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.680 Test value = -0.675 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT098_ALERT_2_C Large Reported Min. (Negative) Residual Density -0.68 eA-3 PLAT213_ALERT_2_C Atom F2B has ADP max/min Ratio ..... 3.10 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14B PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.53 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.17 PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for O1W 145.10 Deg. PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 25 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
Alert level G PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) .. 6 PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000). As a part of a current work of synthesis of such derivatives, in this paper we present the crystal structure of the title compound.

The asymmetric unit consists of two Schiff base molecules [A and B] and one water molecule (Fig. 1). The geometric parameters are comparable to those related structures (Naveenkumar et al., 2009, 2010a, b). The molecules exist in E configurations with respect to the C7AN3A and C7BN3B double bonds. The dihedral angles between the benzene ring and the pyridine ring in molecules A and B are 17.53 (12) and 20.62 (12)°, respectively.

In the crystal structure, the molecules are linked by intermolecular N2A—H2NA···O1B, C7A—H7A···O1B, N2B—H2NB···O1A and C7B—H7B···O1A hydrogen bonds (Table 1) into infinite one-dimensional chains along the a axis. Intermolecular O1W—H1WB···N1B, O1W—H1WA···F2B, C9A—H9A···F2B, C2B—H2B···F1A and C12B—H12B···O1W hydrogen bonds further link these chains into a three-dimensional network (Fig. 2, Table 1). Weak ππ interactions are also observed with Cg1···Cg1vi = 3.6529 (17) Å, Cg2···Cg3v = 3.7092 (16) Å and Cg4···Cg4iv = 3.6495 (17) Å [Cg1, Cg2, Cg3 and Cg4 are centroids of C1A/C2A/N1A/C3A/C4A/C5A, C8A–C13A, C1B/C2B/N1B/C3B/C4B/C5B and C8B–C13B rings, respectively; symmetry code: (iv) 1 - x,2 - y,1 - z; (v) 1 + x,3/2 - y,1/2 + z; (vi) 1 - x,2 - y,-z].

Related literature top

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For the preparation of the title compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The isoniazid derivative was prepared following the procedure by Lourenco et al., 2008. The title compound was prepared by reaction between the 2,4-bis(trifluoro-methyl)benzaldehyde (1.0 eq) with isoniazid (1.0 eq) in ethanol/water. After stirring for 1–3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue, purified by washing with cold ethanol and diethyl ether, afforded the pure derivative. The colourless single-crystals suitable for X-ray analysis was obtained by recrystalization from ethanol.

Refinement top

Hydrogen atoms were positioned geometrically [N-H = 0.86Å, O-H = 0.84Å and C–H = 0.93 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O). The H atoms of the water molecule were included in positions which give ideal geometry for hydrogen bonds.

Structure description top

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000). As a part of a current work of synthesis of such derivatives, in this paper we present the crystal structure of the title compound.

The asymmetric unit consists of two Schiff base molecules [A and B] and one water molecule (Fig. 1). The geometric parameters are comparable to those related structures (Naveenkumar et al., 2009, 2010a, b). The molecules exist in E configurations with respect to the C7AN3A and C7BN3B double bonds. The dihedral angles between the benzene ring and the pyridine ring in molecules A and B are 17.53 (12) and 20.62 (12)°, respectively.

In the crystal structure, the molecules are linked by intermolecular N2A—H2NA···O1B, C7A—H7A···O1B, N2B—H2NB···O1A and C7B—H7B···O1A hydrogen bonds (Table 1) into infinite one-dimensional chains along the a axis. Intermolecular O1W—H1WB···N1B, O1W—H1WA···F2B, C9A—H9A···F2B, C2B—H2B···F1A and C12B—H12B···O1W hydrogen bonds further link these chains into a three-dimensional network (Fig. 2, Table 1). Weak ππ interactions are also observed with Cg1···Cg1vi = 3.6529 (17) Å, Cg2···Cg3v = 3.7092 (16) Å and Cg4···Cg4iv = 3.6495 (17) Å [Cg1, Cg2, Cg3 and Cg4 are centroids of C1A/C2A/N1A/C3A/C4A/C5A, C8A–C13A, C1B/C2B/N1B/C3B/C4B/C5B and C8B–C13B rings, respectively; symmetry code: (iv) 1 - x,2 - y,1 - z; (v) 1 + x,3/2 - y,1/2 + z; (vi) 1 - x,2 - y,-z].

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For the preparation of the title compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom labels and 30% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing of title compound, viewed along the a axis, showing the molecules are linked into a 3-D network. Intermolecular hydrogen bonds are shown as dashed lines.
bis{(E)-N'-[2,4- Bis(trifluoromethyl)benzylidene]isonicotinohydrazide} monohydrate top
Crystal data top
2C15H9F6N3O·H2OF(000) = 1496
Mr = 740.52Dx = 1.602 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8714 reflections
a = 8.2487 (18) Åθ = 2.7–30.0°
b = 26.649 (6) ŵ = 0.16 mm1
c = 14.779 (3) ÅT = 100 K
β = 109.076 (10)°Needle, colourless
V = 3070.3 (11) Å30.59 × 0.17 × 0.13 mm
Z = 4
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
7030 independent reflections
Radiation source: fine-focus sealed tube5239 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1010
Tmin = 0.914, Tmax = 0.980k = 3434
29846 measured reflectionsl = 1919
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0688P)2 + 3.4968P]
where P = (Fo2 + 2Fc2)/3
7030 reflections(Δ/σ)max = 0.001
460 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.68 e Å3
Crystal data top
2C15H9F6N3O·H2OV = 3070.3 (11) Å3
Mr = 740.52Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.2487 (18) ŵ = 0.16 mm1
b = 26.649 (6) ÅT = 100 K
c = 14.779 (3) Å0.59 × 0.17 × 0.13 mm
β = 109.076 (10)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
7030 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5239 reflections with I > 2σ(I)
Tmin = 0.914, Tmax = 0.980Rint = 0.030
29846 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.02Δρmax = 0.67 e Å3
7030 reflectionsΔρmin = 0.68 e Å3
460 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
F1A1.3386 (2)0.67680 (7)0.46754 (17)0.0730 (6)
F2A1.2638 (3)0.64562 (7)0.32715 (17)0.0769 (7)
F3A1.1394 (2)0.62210 (6)0.42543 (13)0.0516 (4)
F4A0.53442 (19)0.72504 (6)0.14372 (11)0.0436 (4)
F5A0.57719 (19)0.66261 (5)0.24013 (13)0.0453 (4)
F6A0.49749 (17)0.73324 (5)0.27950 (11)0.0372 (3)
O1A0.83293 (19)0.95521 (6)0.18897 (12)0.0307 (4)
N1A0.2710 (3)1.04566 (8)0.05493 (16)0.0387 (5)
N2A0.6377 (2)0.89622 (6)0.19410 (14)0.0276 (4)
H2NA0.53150.88880.18280.033*
N3A0.7647 (2)0.86131 (6)0.23267 (14)0.0266 (4)
C1A0.3807 (3)0.96185 (8)0.07092 (17)0.0285 (5)
H1A0.36140.92810.05520.034*
C2A0.2523 (3)0.99707 (9)0.03320 (18)0.0346 (5)
H2A0.14810.98620.00930.041*
C3A0.4233 (3)1.06017 (8)0.11472 (19)0.0366 (5)
H3A0.43791.09390.13120.044*
C4A0.5604 (3)1.02840 (8)0.15360 (17)0.0298 (5)
H4A0.66521.04070.19300.036*
C5A0.5379 (3)0.97783 (7)0.13241 (15)0.0237 (4)
C6A0.6844 (3)0.94253 (7)0.17445 (16)0.0246 (4)
C7A0.7099 (3)0.81749 (8)0.24256 (17)0.0286 (5)
H7A0.59280.81110.22410.034*
C8A0.8339 (3)0.77756 (8)0.28328 (16)0.0265 (4)
C9A1.0062 (3)0.78936 (8)0.32681 (17)0.0292 (5)
H9A1.04080.82270.33050.035*
C10A1.1269 (3)0.75252 (9)0.36459 (17)0.0330 (5)
H10A1.24180.76090.39340.040*
C11A1.0749 (3)0.70289 (9)0.35908 (18)0.0339 (5)
C12A0.9041 (3)0.69018 (8)0.31789 (18)0.0328 (5)
H12A0.87020.65680.31580.039*
C13A0.7835 (3)0.72720 (8)0.27974 (17)0.0279 (5)
C14A1.2037 (3)0.66203 (10)0.3951 (2)0.0460 (7)
C15A0.5987 (3)0.71217 (8)0.23552 (18)0.0324 (5)
F1B0.9350 (3)1.07132 (10)0.53923 (16)0.0896 (8)
F2B0.7582 (4)1.12296 (12)0.5572 (2)0.1222 (12)
F3B0.8325 (3)1.12608 (8)0.43264 (16)0.0815 (7)
F4B0.0666 (2)1.04165 (6)0.38057 (14)0.0563 (5)
F5B0.1590 (3)1.11618 (6)0.37229 (16)0.0672 (6)
F6B0.0833 (2)1.06925 (6)0.24796 (14)0.0566 (5)
O1B0.3278 (2)0.84289 (7)0.17464 (18)0.0525 (6)
N1B0.2255 (3)0.75716 (8)0.00655 (16)0.0357 (5)
N2B0.1387 (2)0.89800 (7)0.19927 (14)0.0291 (4)
H2NB0.03380.90610.19090.035*
N3B0.2726 (2)0.92809 (7)0.25030 (14)0.0309 (4)
C1B0.1252 (3)0.84074 (8)0.05378 (17)0.0298 (5)
H1B0.14840.87500.05050.036*
C2B0.2489 (3)0.80662 (9)0.00503 (18)0.0337 (5)
H2B0.35580.81900.03130.040*
C3B0.0697 (3)0.74026 (9)0.05774 (19)0.0360 (5)
H3B0.04980.70590.05940.043*
C4B0.0630 (3)0.77130 (8)0.10816 (19)0.0335 (5)
H4B0.16990.75800.14200.040*
C5B0.0346 (3)0.82255 (8)0.10771 (17)0.0280 (5)
C6B0.1793 (3)0.85540 (8)0.16307 (19)0.0326 (5)
C7B0.2332 (3)0.96770 (9)0.28583 (17)0.0311 (5)
H7B0.11930.97570.27690.037*
C8B0.3734 (3)1.00068 (9)0.34169 (17)0.0322 (5)
C9B0.5420 (3)0.98353 (10)0.36821 (17)0.0359 (5)
H9B0.56340.95090.35300.043*
C10B0.6783 (3)1.01409 (11)0.41673 (18)0.0418 (6)
H10B0.79041.00240.43250.050*
C11B0.6459 (4)1.06192 (11)0.44127 (18)0.0448 (7)
C12B0.4801 (4)1.07976 (10)0.41867 (19)0.0434 (6)
H12B0.46001.11190.43700.052*
C13B0.3433 (3)1.04929 (9)0.36825 (18)0.0372 (6)
C14B0.7939 (5)1.09561 (14)0.4928 (2)0.0605 (9)
C15B0.1644 (4)1.06914 (10)0.3428 (2)0.0480 (7)
O1W0.5352 (5)0.82564 (14)0.4292 (3)0.1324 (16)
H1WA0.44870.84090.43310.199*
H1WB0.60410.80200.45120.199*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0290 (9)0.0562 (11)0.1136 (17)0.0121 (8)0.0043 (9)0.0302 (11)
F2A0.0817 (15)0.0613 (12)0.1128 (17)0.0463 (11)0.0660 (14)0.0371 (11)
F3A0.0366 (9)0.0357 (8)0.0809 (12)0.0138 (7)0.0172 (8)0.0275 (8)
F4A0.0327 (8)0.0454 (8)0.0458 (8)0.0101 (6)0.0034 (6)0.0051 (7)
F5A0.0328 (8)0.0190 (6)0.0825 (11)0.0040 (6)0.0165 (8)0.0044 (7)
F6A0.0224 (7)0.0308 (7)0.0593 (9)0.0017 (5)0.0146 (6)0.0057 (6)
O1A0.0182 (8)0.0218 (7)0.0493 (10)0.0021 (6)0.0074 (7)0.0024 (7)
N1A0.0335 (11)0.0314 (10)0.0519 (13)0.0132 (9)0.0148 (10)0.0085 (9)
N2A0.0159 (8)0.0177 (8)0.0468 (11)0.0019 (6)0.0071 (8)0.0052 (7)
N3A0.0191 (9)0.0193 (8)0.0388 (10)0.0037 (7)0.0061 (7)0.0040 (7)
C1A0.0211 (10)0.0203 (10)0.0425 (12)0.0008 (8)0.0083 (9)0.0023 (9)
C2A0.0223 (11)0.0314 (12)0.0477 (14)0.0049 (9)0.0083 (10)0.0068 (10)
C3A0.0455 (15)0.0180 (10)0.0490 (14)0.0064 (10)0.0191 (12)0.0015 (9)
C4A0.0308 (12)0.0186 (10)0.0400 (12)0.0023 (8)0.0115 (10)0.0004 (9)
C5A0.0182 (10)0.0167 (9)0.0370 (11)0.0001 (7)0.0099 (8)0.0028 (8)
C6A0.0189 (10)0.0170 (9)0.0362 (11)0.0005 (7)0.0069 (8)0.0004 (8)
C7A0.0179 (10)0.0207 (10)0.0447 (12)0.0010 (8)0.0068 (9)0.0049 (9)
C8A0.0216 (10)0.0208 (10)0.0358 (11)0.0020 (8)0.0077 (9)0.0046 (8)
C9A0.0231 (11)0.0235 (10)0.0389 (12)0.0009 (8)0.0072 (9)0.0040 (9)
C10A0.0212 (11)0.0335 (12)0.0415 (13)0.0030 (9)0.0065 (9)0.0081 (10)
C11A0.0275 (12)0.0298 (11)0.0458 (13)0.0087 (9)0.0137 (10)0.0113 (10)
C12A0.0277 (12)0.0217 (10)0.0502 (14)0.0053 (9)0.0147 (10)0.0079 (9)
C13A0.0217 (11)0.0219 (10)0.0400 (12)0.0022 (8)0.0101 (9)0.0049 (9)
C14A0.0290 (13)0.0408 (14)0.0705 (19)0.0131 (11)0.0193 (13)0.0205 (13)
C15A0.0267 (11)0.0197 (10)0.0501 (14)0.0001 (8)0.0116 (10)0.0053 (9)
F1B0.0616 (14)0.1076 (18)0.0721 (14)0.0456 (13)0.0158 (11)0.0014 (12)
F2B0.109 (2)0.157 (3)0.117 (2)0.089 (2)0.0587 (17)0.099 (2)
F3B0.0739 (14)0.0757 (14)0.0837 (14)0.0487 (12)0.0104 (11)0.0088 (11)
F4B0.0472 (10)0.0400 (9)0.0904 (13)0.0042 (7)0.0346 (9)0.0085 (8)
F5B0.0679 (13)0.0311 (8)0.1054 (16)0.0032 (8)0.0319 (11)0.0196 (9)
F6B0.0495 (10)0.0355 (8)0.0743 (12)0.0027 (7)0.0057 (9)0.0018 (8)
O1B0.0177 (9)0.0292 (9)0.1087 (17)0.0001 (7)0.0179 (9)0.0146 (10)
N1B0.0288 (10)0.0309 (10)0.0492 (12)0.0074 (8)0.0151 (9)0.0048 (9)
N2B0.0140 (8)0.0239 (9)0.0475 (11)0.0008 (7)0.0072 (8)0.0026 (8)
N3B0.0197 (9)0.0273 (9)0.0421 (11)0.0050 (7)0.0054 (8)0.0004 (8)
C1B0.0224 (11)0.0239 (10)0.0436 (13)0.0035 (8)0.0113 (9)0.0010 (9)
C2B0.0213 (11)0.0340 (12)0.0441 (13)0.0002 (9)0.0083 (9)0.0028 (10)
C3B0.0341 (13)0.0216 (11)0.0552 (15)0.0009 (9)0.0185 (11)0.0001 (10)
C4B0.0250 (11)0.0232 (11)0.0517 (14)0.0024 (9)0.0116 (10)0.0016 (10)
C5B0.0199 (10)0.0219 (10)0.0446 (13)0.0003 (8)0.0135 (9)0.0011 (9)
C6B0.0188 (11)0.0226 (10)0.0548 (14)0.0003 (8)0.0098 (10)0.0011 (10)
C7B0.0221 (11)0.0294 (11)0.0411 (12)0.0028 (9)0.0094 (9)0.0010 (9)
C8B0.0294 (12)0.0321 (12)0.0349 (12)0.0089 (9)0.0100 (9)0.0013 (9)
C9B0.0284 (12)0.0429 (13)0.0355 (12)0.0084 (10)0.0091 (10)0.0034 (10)
C10B0.0317 (13)0.0570 (17)0.0349 (13)0.0158 (12)0.0085 (10)0.0050 (11)
C11B0.0447 (16)0.0560 (17)0.0330 (12)0.0245 (13)0.0118 (11)0.0063 (11)
C12B0.0554 (17)0.0361 (13)0.0421 (14)0.0186 (12)0.0206 (12)0.0072 (11)
C13B0.0402 (14)0.0325 (12)0.0407 (13)0.0098 (10)0.0157 (11)0.0028 (10)
C14B0.062 (2)0.066 (2)0.0557 (18)0.0345 (17)0.0222 (17)0.0206 (16)
C15B0.0508 (17)0.0283 (12)0.0659 (19)0.0044 (11)0.0207 (14)0.0073 (12)
O1W0.119 (3)0.109 (3)0.134 (3)0.069 (2)0.006 (2)0.044 (2)
Geometric parameters (Å, º) top
F1A—C14A1.326 (4)F2B—C14B1.306 (4)
F2A—C14A1.331 (4)F3B—C14B1.317 (4)
F3A—C14A1.331 (3)F4B—C15B1.339 (3)
F4A—C15A1.330 (3)F5B—C15B1.333 (3)
F5A—C15A1.337 (3)F6B—C15B1.341 (4)
F6A—C15A1.338 (3)O1B—C6B1.226 (3)
O1A—C6A1.221 (3)N1B—C2B1.331 (3)
N1A—C2A1.331 (3)N1B—C3B1.339 (3)
N1A—C3A1.336 (3)N2B—C6B1.343 (3)
N2A—C6A1.352 (3)N2B—N3B1.374 (3)
N2A—N3A1.377 (2)N2B—H2NB0.8600
N2A—H2NA0.8600N3B—C7B1.268 (3)
N3A—C7A1.277 (3)C1B—C2B1.381 (3)
C1A—C5A1.385 (3)C1B—C5B1.386 (3)
C1A—C2A1.388 (3)C1B—H1B0.9300
C1A—H1A0.9300C2B—H2B0.9300
C2A—H2A0.9300C3B—C4B1.380 (3)
C3A—C4A1.379 (3)C3B—H3B0.9300
C3A—H3A0.9300C4B—C5B1.385 (3)
C4A—C5A1.382 (3)C4B—H4B0.9300
C4A—H4A0.9300C5B—C6B1.490 (3)
C5A—C6A1.496 (3)C7B—C8B1.472 (3)
C7A—C8A1.462 (3)C7B—H7B0.9300
C7A—H7A0.9300C8B—C9B1.393 (4)
C8A—C9A1.392 (3)C8B—C13B1.399 (3)
C8A—C13A1.401 (3)C9B—C10B1.383 (3)
C9A—C10A1.380 (3)C9B—H9B0.9300
C9A—H9A0.9300C10B—C11B1.375 (4)
C10A—C11A1.385 (3)C10B—H10B0.9300
C10A—H10A0.9300C11B—C12B1.382 (4)
C11A—C12A1.382 (3)C11B—C14B1.506 (4)
C11A—C14A1.493 (3)C12B—C13B1.392 (4)
C12A—C13A1.384 (3)C12B—H12B0.9300
C12A—H12A0.9300C13B—C15B1.496 (4)
C13A—C15A1.503 (3)O1W—H1WA0.8400
F1B—C14B1.313 (5)O1W—H1WB0.8400
C2A—N1A—C3A116.8 (2)C6B—N2B—N3B116.85 (18)
C6A—N2A—N3A118.29 (17)C6B—N2B—H2NB121.6
C6A—N2A—H2NA120.9N3B—N2B—H2NB121.6
N3A—N2A—H2NA120.9C7B—N3B—N2B116.41 (19)
C7A—N3A—N2A114.54 (18)C2B—C1B—C5B118.1 (2)
C5A—C1A—C2A118.9 (2)C2B—C1B—H1B120.9
C5A—C1A—H1A120.5C5B—C1B—H1B120.9
C2A—C1A—H1A120.5N1B—C2B—C1B124.4 (2)
N1A—C2A—C1A123.2 (2)N1B—C2B—H2B117.8
N1A—C2A—H2A118.4C1B—C2B—H2B117.8
C1A—C2A—H2A118.4N1B—C3B—C4B123.3 (2)
N1A—C3A—C4A124.3 (2)N1B—C3B—H3B118.3
N1A—C3A—H3A117.8C4B—C3B—H3B118.3
C4A—C3A—H3A117.8C3B—C4B—C5B119.0 (2)
C3A—C4A—C5A118.3 (2)C3B—C4B—H4B120.5
C3A—C4A—H4A120.9C5B—C4B—H4B120.5
C5A—C4A—H4A120.9C4B—C5B—C1B118.4 (2)
C4A—C5A—C1A118.4 (2)C4B—C5B—C6B118.2 (2)
C4A—C5A—C6A119.25 (19)C1B—C5B—C6B123.4 (2)
C1A—C5A—C6A122.32 (18)O1B—C6B—N2B122.8 (2)
O1A—C6A—N2A123.70 (19)O1B—C6B—C5B120.0 (2)
O1A—C6A—C5A121.77 (18)N2B—C6B—C5B117.14 (19)
N2A—C6A—C5A114.53 (18)N3B—C7B—C8B118.0 (2)
N3A—C7A—C8A119.11 (19)N3B—C7B—H7B121.0
N3A—C7A—H7A120.4C8B—C7B—H7B121.0
C8A—C7A—H7A120.4C9B—C8B—C13B118.5 (2)
C9A—C8A—C13A118.67 (19)C9B—C8B—C7B119.4 (2)
C9A—C8A—C7A119.81 (19)C13B—C8B—C7B122.1 (2)
C13A—C8A—C7A121.51 (19)C10B—C9B—C8B121.3 (3)
C10A—C9A—C8A121.3 (2)C10B—C9B—H9B119.3
C10A—C9A—H9A119.4C8B—C9B—H9B119.3
C8A—C9A—H9A119.4C11B—C10B—C9B119.2 (3)
C9A—C10A—C11A119.2 (2)C11B—C10B—H10B120.4
C9A—C10A—H10A120.4C9B—C10B—H10B120.4
C11A—C10A—H10A120.4C10B—C11B—C12B121.1 (2)
C12A—C11A—C10A120.8 (2)C10B—C11B—C14B119.4 (3)
C12A—C11A—C14A118.9 (2)C12B—C11B—C14B119.4 (3)
C10A—C11A—C14A120.3 (2)C11B—C12B—C13B119.6 (3)
C11A—C12A—C13A119.9 (2)C11B—C12B—H12B120.2
C11A—C12A—H12A120.1C13B—C12B—H12B120.2
C13A—C12A—H12A120.1C12B—C13B—C8B120.2 (3)
C12A—C13A—C8A120.2 (2)C12B—C13B—C15B119.3 (2)
C12A—C13A—C15A118.6 (2)C8B—C13B—C15B120.5 (2)
C8A—C13A—C15A121.20 (19)F2B—C14B—F1B105.4 (3)
F1A—C14A—F3A106.7 (2)F2B—C14B—F3B108.0 (3)
F1A—C14A—F2A106.6 (2)F1B—C14B—F3B106.8 (3)
F3A—C14A—F2A106.2 (2)F2B—C14B—C11B111.3 (3)
F1A—C14A—C11A112.5 (2)F1B—C14B—C11B113.8 (3)
F3A—C14A—C11A112.8 (2)F3B—C14B—C11B111.2 (3)
F2A—C14A—C11A111.6 (2)F5B—C15B—F4B106.8 (2)
F4A—C15A—F5A106.9 (2)F5B—C15B—F6B106.3 (2)
F4A—C15A—F6A106.45 (19)F4B—C15B—F6B105.9 (2)
F5A—C15A—F6A105.99 (19)F5B—C15B—C13B112.7 (2)
F4A—C15A—C13A112.60 (19)F4B—C15B—C13B112.4 (2)
F5A—C15A—C13A111.95 (19)F6B—C15B—C13B112.2 (2)
F6A—C15A—C13A112.5 (2)H1WA—O1W—H1WB145.0
C2B—N1B—C3B116.7 (2)
C6A—N2A—N3A—C7A175.0 (2)C6B—N2B—N3B—C7B178.6 (2)
C3A—N1A—C2A—C1A1.3 (4)C3B—N1B—C2B—C1B1.3 (4)
C5A—C1A—C2A—N1A1.7 (4)C5B—C1B—C2B—N1B0.3 (4)
C2A—N1A—C3A—C4A0.8 (4)C2B—N1B—C3B—C4B0.6 (4)
N1A—C3A—C4A—C5A2.4 (4)N1B—C3B—C4B—C5B1.1 (4)
C3A—C4A—C5A—C1A2.0 (3)C3B—C4B—C5B—C1B2.1 (4)
C3A—C4A—C5A—C6A179.5 (2)C3B—C4B—C5B—C6B179.6 (2)
C2A—C1A—C5A—C4A0.1 (3)C2B—C1B—C5B—C4B1.4 (4)
C2A—C1A—C5A—C6A178.6 (2)C2B—C1B—C5B—C6B179.6 (2)
N3A—N2A—C6A—O1A0.0 (3)N3B—N2B—C6B—O1B0.6 (4)
N3A—N2A—C6A—C5A179.77 (18)N3B—N2B—C6B—C5B179.9 (2)
C4A—C5A—C6A—O1A33.3 (3)C4B—C5B—C6B—O1B29.3 (4)
C1A—C5A—C6A—O1A145.2 (2)C1B—C5B—C6B—O1B148.9 (3)
C4A—C5A—C6A—N2A146.9 (2)C4B—C5B—C6B—N2B150.0 (2)
C1A—C5A—C6A—N2A34.6 (3)C1B—C5B—C6B—N2B31.8 (4)
N2A—N3A—C7A—C8A179.7 (2)N2B—N3B—C7B—C8B179.5 (2)
N3A—C7A—C8A—C9A12.0 (3)N3B—C7B—C8B—C9B11.4 (3)
N3A—C7A—C8A—C13A168.1 (2)N3B—C7B—C8B—C13B167.7 (2)
C13A—C8A—C9A—C10A1.1 (4)C13B—C8B—C9B—C10B2.3 (4)
C7A—C8A—C9A—C10A179.0 (2)C7B—C8B—C9B—C10B176.9 (2)
C8A—C9A—C10A—C11A0.1 (4)C8B—C9B—C10B—C11B1.7 (4)
C9A—C10A—C11A—C12A1.1 (4)C9B—C10B—C11B—C12B0.3 (4)
C9A—C10A—C11A—C14A177.1 (2)C9B—C10B—C11B—C14B179.1 (3)
C10A—C11A—C12A—C13A1.4 (4)C10B—C11B—C12B—C13B1.5 (4)
C14A—C11A—C12A—C13A176.8 (2)C14B—C11B—C12B—C13B177.9 (3)
C11A—C12A—C13A—C8A0.4 (4)C11B—C12B—C13B—C8B0.8 (4)
C11A—C12A—C13A—C15A180.0 (2)C11B—C12B—C13B—C15B179.1 (3)
C9A—C8A—C13A—C12A0.8 (3)C9B—C8B—C13B—C12B1.0 (4)
C7A—C8A—C13A—C12A179.2 (2)C7B—C8B—C13B—C12B178.1 (2)
C9A—C8A—C13A—C15A178.7 (2)C9B—C8B—C13B—C15B179.0 (2)
C7A—C8A—C13A—C15A1.2 (4)C7B—C8B—C13B—C15B1.8 (4)
C12A—C11A—C14A—F1A151.1 (2)C10B—C11B—C14B—F2B142.1 (3)
C10A—C11A—C14A—F1A30.6 (4)C12B—C11B—C14B—F2B38.5 (4)
C12A—C11A—C14A—F3A30.4 (4)C10B—C11B—C14B—F1B23.1 (4)
C10A—C11A—C14A—F3A151.4 (3)C12B—C11B—C14B—F1B157.5 (3)
C12A—C11A—C14A—F2A89.1 (3)C10B—C11B—C14B—F3B97.5 (4)
C10A—C11A—C14A—F2A89.1 (3)C12B—C11B—C14B—F3B81.9 (4)
C12A—C13A—C15A—F4A120.3 (2)C12B—C13B—C15B—F5B0.8 (4)
C8A—C13A—C15A—F4A60.1 (3)C8B—C13B—C15B—F5B179.1 (2)
C12A—C13A—C15A—F5A0.2 (3)C12B—C13B—C15B—F4B120.0 (3)
C8A—C13A—C15A—F5A179.4 (2)C8B—C13B—C15B—F4B60.1 (3)
C12A—C13A—C15A—F6A119.4 (2)C12B—C13B—C15B—F6B120.8 (3)
C8A—C13A—C15A—F6A60.2 (3)C8B—C13B—C15B—F6B59.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1B0.862.052.856 (3)156
N2B—H2NB···O1Ai0.862.102.908 (3)155
C7A—H7A···O1B0.932.233.055 (3)147
C7B—H7B···O1Ai0.932.363.158 (3)144
C2B—H2B···F1Aii0.932.523.294 (3)141
C9A—H9A···F2Biii0.932.413.162 (4)138
C12B—H12B···O1Wiv0.932.583.408 (5)149
O1W—H1WA···F2Biv0.842.012.845 (5)180
O1W—H1WB···N1Bv0.842.092.932 (5)180
Symmetry codes: (i) x1, y, z; (ii) x2, y+3/2, z1/2; (iii) x+2, y+2, z+1; (iv) x+1, y+2, z+1; (v) x+1, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula2C15H9F6N3O·H2O
Mr740.52
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.2487 (18), 26.649 (6), 14.779 (3)
β (°) 109.076 (10)
V3)3070.3 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.59 × 0.17 × 0.13
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.914, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
29846, 7030, 5239
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.162, 1.02
No. of reflections7030
No. of parameters460
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.68

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1B0.862.052.856 (3)156
N2B—H2NB···O1Ai0.862.102.908 (3)155
C7A—H7A···O1B0.932.233.055 (3)147
C7B—H7B···O1Ai0.932.363.158 (3)144
C2B—H2B···F1Aii0.932.523.294 (3)141
C9A—H9A···F2Biii0.932.413.162 (4)138
C12B—H12B···O1Wiv0.932.583.408 (5)149
O1W—H1WA···F2Biv0.842.012.845 (5)180
O1W—H1WB···N1Bv0.842.092.932 (5)180
Symmetry codes: (i) x1, y, z; (ii) x2, y+3/2, z1/2; (iii) x+2, y+2, z+1; (iv) x+1, y+2, z+1; (v) x+1, y+3/2, z+1/2.
 

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