







Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810025493/lh5074sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810025493/lh5074Isup2.hkl |
CCDC reference: 788323
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(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
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.
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.
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 C7A═N3A and C7B═N3B 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 π–π 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).
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).
2C15H9F6N3O·H2O | F(000) = 1496 |
Mr = 740.52 | Dx = 1.602 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8714 reflections |
a = 8.2487 (18) Å | θ = 2.7–30.0° |
b = 26.649 (6) Å | µ = 0.16 mm−1 |
c = 14.779 (3) Å | T = 100 K |
β = 109.076 (10)° | Needle, colourless |
V = 3070.3 (11) Å3 | 0.59 × 0.17 × 0.13 mm |
Z = 4 |
Bruker APEXII DUO CCD area-detector diffractometer | 7030 independent reflections |
Radiation source: fine-focus sealed tube | 5239 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −10→10 |
Tmin = 0.914, Tmax = 0.980 | k = −34→34 |
29846 measured reflections | l = −19→19 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-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 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
2C15H9F6N3O·H2O | V = 3070.3 (11) Å3 |
Mr = 740.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.2487 (18) Å | µ = 0.16 mm−1 |
b = 26.649 (6) Å | T = 100 K |
c = 14.779 (3) Å | 0.59 × 0.17 × 0.13 mm |
β = 109.076 (10)° |
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 = 0.980 | Rint = 0.030 |
29846 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.67 e Å−3 |
7030 reflections | Δρmin = −0.68 e Å−3 |
460 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
F1A | 1.3386 (2) | 0.67680 (7) | 0.46754 (17) | 0.0730 (6) | |
F2A | 1.2638 (3) | 0.64562 (7) | 0.32715 (17) | 0.0769 (7) | |
F3A | 1.1394 (2) | 0.62210 (6) | 0.42543 (13) | 0.0516 (4) | |
F4A | 0.53442 (19) | 0.72504 (6) | 0.14372 (11) | 0.0436 (4) | |
F5A | 0.57719 (19) | 0.66261 (5) | 0.24013 (13) | 0.0453 (4) | |
F6A | 0.49749 (17) | 0.73324 (5) | 0.27950 (11) | 0.0372 (3) | |
O1A | 0.83293 (19) | 0.95521 (6) | 0.18897 (12) | 0.0307 (4) | |
N1A | 0.2710 (3) | 1.04566 (8) | 0.05493 (16) | 0.0387 (5) | |
N2A | 0.6377 (2) | 0.89622 (6) | 0.19410 (14) | 0.0276 (4) | |
H2NA | 0.5315 | 0.8888 | 0.1828 | 0.033* | |
N3A | 0.7647 (2) | 0.86131 (6) | 0.23267 (14) | 0.0266 (4) | |
C1A | 0.3807 (3) | 0.96185 (8) | 0.07092 (17) | 0.0285 (5) | |
H1A | 0.3614 | 0.9281 | 0.0552 | 0.034* | |
C2A | 0.2523 (3) | 0.99707 (9) | 0.03320 (18) | 0.0346 (5) | |
H2A | 0.1481 | 0.9862 | −0.0093 | 0.041* | |
C3A | 0.4233 (3) | 1.06017 (8) | 0.11472 (19) | 0.0366 (5) | |
H3A | 0.4379 | 1.0939 | 0.1312 | 0.044* | |
C4A | 0.5604 (3) | 1.02840 (8) | 0.15360 (17) | 0.0298 (5) | |
H4A | 0.6652 | 1.0407 | 0.1930 | 0.036* | |
C5A | 0.5379 (3) | 0.97783 (7) | 0.13241 (15) | 0.0237 (4) | |
C6A | 0.6844 (3) | 0.94253 (7) | 0.17445 (16) | 0.0246 (4) | |
C7A | 0.7099 (3) | 0.81749 (8) | 0.24256 (17) | 0.0286 (5) | |
H7A | 0.5928 | 0.8111 | 0.2241 | 0.034* | |
C8A | 0.8339 (3) | 0.77756 (8) | 0.28328 (16) | 0.0265 (4) | |
C9A | 1.0062 (3) | 0.78936 (8) | 0.32681 (17) | 0.0292 (5) | |
H9A | 1.0408 | 0.8227 | 0.3305 | 0.035* | |
C10A | 1.1269 (3) | 0.75252 (9) | 0.36459 (17) | 0.0330 (5) | |
H10A | 1.2418 | 0.7609 | 0.3934 | 0.040* | |
C11A | 1.0749 (3) | 0.70289 (9) | 0.35908 (18) | 0.0339 (5) | |
C12A | 0.9041 (3) | 0.69018 (8) | 0.31789 (18) | 0.0328 (5) | |
H12A | 0.8702 | 0.6568 | 0.3158 | 0.039* | |
C13A | 0.7835 (3) | 0.72720 (8) | 0.27974 (17) | 0.0279 (5) | |
C14A | 1.2037 (3) | 0.66203 (10) | 0.3951 (2) | 0.0460 (7) | |
C15A | 0.5987 (3) | 0.71217 (8) | 0.23552 (18) | 0.0324 (5) | |
F1B | 0.9350 (3) | 1.07132 (10) | 0.53923 (16) | 0.0896 (8) | |
F2B | 0.7582 (4) | 1.12296 (12) | 0.5572 (2) | 0.1222 (12) | |
F3B | 0.8325 (3) | 1.12608 (8) | 0.43264 (16) | 0.0815 (7) | |
F4B | 0.0666 (2) | 1.04165 (6) | 0.38057 (14) | 0.0563 (5) | |
F5B | 0.1590 (3) | 1.11618 (6) | 0.37229 (16) | 0.0672 (6) | |
F6B | 0.0833 (2) | 1.06925 (6) | 0.24796 (14) | 0.0566 (5) | |
O1B | 0.3278 (2) | 0.84289 (7) | 0.17464 (18) | 0.0525 (6) | |
N1B | −0.2255 (3) | 0.75716 (8) | 0.00655 (16) | 0.0357 (5) | |
N2B | 0.1387 (2) | 0.89800 (7) | 0.19927 (14) | 0.0291 (4) | |
H2NB | 0.0338 | 0.9061 | 0.1909 | 0.035* | |
N3B | 0.2726 (2) | 0.92809 (7) | 0.25030 (14) | 0.0309 (4) | |
C1B | −0.1252 (3) | 0.84074 (8) | 0.05378 (17) | 0.0298 (5) | |
H1B | −0.1484 | 0.8750 | 0.0505 | 0.036* | |
C2B | −0.2489 (3) | 0.80662 (9) | 0.00503 (18) | 0.0337 (5) | |
H2B | −0.3558 | 0.8190 | −0.0313 | 0.040* | |
C3B | −0.0697 (3) | 0.74026 (9) | 0.05774 (19) | 0.0360 (5) | |
H3B | −0.0498 | 0.7059 | 0.0594 | 0.043* | |
C4B | 0.0630 (3) | 0.77130 (8) | 0.10816 (19) | 0.0335 (5) | |
H4B | 0.1699 | 0.7580 | 0.1420 | 0.040* | |
C5B | 0.0346 (3) | 0.82255 (8) | 0.10771 (17) | 0.0280 (5) | |
C6B | 0.1793 (3) | 0.85540 (8) | 0.16307 (19) | 0.0326 (5) | |
C7B | 0.2332 (3) | 0.96770 (9) | 0.28583 (17) | 0.0311 (5) | |
H7B | 0.1193 | 0.9757 | 0.2769 | 0.037* | |
C8B | 0.3734 (3) | 1.00068 (9) | 0.34169 (17) | 0.0322 (5) | |
C9B | 0.5420 (3) | 0.98353 (10) | 0.36821 (17) | 0.0359 (5) | |
H9B | 0.5634 | 0.9509 | 0.3530 | 0.043* | |
C10B | 0.6783 (3) | 1.01409 (11) | 0.41673 (18) | 0.0418 (6) | |
H10B | 0.7904 | 1.0024 | 0.4325 | 0.050* | |
C11B | 0.6459 (4) | 1.06192 (11) | 0.44127 (18) | 0.0448 (7) | |
C12B | 0.4801 (4) | 1.07976 (10) | 0.41867 (19) | 0.0434 (6) | |
H12B | 0.4600 | 1.1119 | 0.4370 | 0.052* | |
C13B | 0.3433 (3) | 1.04929 (9) | 0.36825 (18) | 0.0372 (6) | |
C14B | 0.7939 (5) | 1.09561 (14) | 0.4928 (2) | 0.0605 (9) | |
C15B | 0.1644 (4) | 1.06914 (10) | 0.3428 (2) | 0.0480 (7) | |
O1W | 0.5352 (5) | 0.82564 (14) | 0.4292 (3) | 0.1324 (16) | |
H1WA | 0.4487 | 0.8409 | 0.4331 | 0.199* | |
H1WB | 0.6041 | 0.8020 | 0.4512 | 0.199* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1A | 0.0290 (9) | 0.0562 (11) | 0.1136 (17) | 0.0121 (8) | −0.0043 (9) | 0.0302 (11) |
F2A | 0.0817 (15) | 0.0613 (12) | 0.1128 (17) | 0.0463 (11) | 0.0660 (14) | 0.0371 (11) |
F3A | 0.0366 (9) | 0.0357 (8) | 0.0809 (12) | 0.0138 (7) | 0.0172 (8) | 0.0275 (8) |
F4A | 0.0327 (8) | 0.0454 (8) | 0.0458 (8) | −0.0101 (6) | 0.0034 (6) | 0.0051 (7) |
F5A | 0.0328 (8) | 0.0190 (6) | 0.0825 (11) | −0.0040 (6) | 0.0165 (8) | 0.0044 (7) |
F6A | 0.0224 (7) | 0.0308 (7) | 0.0593 (9) | 0.0017 (5) | 0.0146 (6) | 0.0057 (6) |
O1A | 0.0182 (8) | 0.0218 (7) | 0.0493 (10) | −0.0021 (6) | 0.0074 (7) | 0.0024 (7) |
N1A | 0.0335 (11) | 0.0314 (10) | 0.0519 (13) | 0.0132 (9) | 0.0148 (10) | 0.0085 (9) |
N2A | 0.0159 (8) | 0.0177 (8) | 0.0468 (11) | 0.0019 (6) | 0.0071 (8) | 0.0052 (7) |
N3A | 0.0191 (9) | 0.0193 (8) | 0.0388 (10) | 0.0037 (7) | 0.0061 (7) | 0.0040 (7) |
C1A | 0.0211 (10) | 0.0203 (10) | 0.0425 (12) | −0.0008 (8) | 0.0083 (9) | 0.0023 (9) |
C2A | 0.0223 (11) | 0.0314 (12) | 0.0477 (14) | 0.0049 (9) | 0.0083 (10) | 0.0068 (10) |
C3A | 0.0455 (15) | 0.0180 (10) | 0.0490 (14) | 0.0064 (10) | 0.0191 (12) | 0.0015 (9) |
C4A | 0.0308 (12) | 0.0186 (10) | 0.0400 (12) | −0.0023 (8) | 0.0115 (10) | −0.0004 (9) |
C5A | 0.0182 (10) | 0.0167 (9) | 0.0370 (11) | −0.0001 (7) | 0.0099 (8) | 0.0028 (8) |
C6A | 0.0189 (10) | 0.0170 (9) | 0.0362 (11) | −0.0005 (7) | 0.0069 (8) | −0.0004 (8) |
C7A | 0.0179 (10) | 0.0207 (10) | 0.0447 (12) | 0.0010 (8) | 0.0068 (9) | 0.0049 (9) |
C8A | 0.0216 (10) | 0.0208 (10) | 0.0358 (11) | 0.0020 (8) | 0.0077 (9) | 0.0046 (8) |
C9A | 0.0231 (11) | 0.0235 (10) | 0.0389 (12) | −0.0009 (8) | 0.0072 (9) | 0.0040 (9) |
C10A | 0.0212 (11) | 0.0335 (12) | 0.0415 (13) | 0.0030 (9) | 0.0065 (9) | 0.0081 (10) |
C11A | 0.0275 (12) | 0.0298 (11) | 0.0458 (13) | 0.0087 (9) | 0.0137 (10) | 0.0113 (10) |
C12A | 0.0277 (12) | 0.0217 (10) | 0.0502 (14) | 0.0053 (9) | 0.0147 (10) | 0.0079 (9) |
C13A | 0.0217 (11) | 0.0219 (10) | 0.0400 (12) | 0.0022 (8) | 0.0101 (9) | 0.0049 (9) |
C14A | 0.0290 (13) | 0.0408 (14) | 0.0705 (19) | 0.0131 (11) | 0.0193 (13) | 0.0205 (13) |
C15A | 0.0267 (11) | 0.0197 (10) | 0.0501 (14) | −0.0001 (8) | 0.0116 (10) | 0.0053 (9) |
F1B | 0.0616 (14) | 0.1076 (18) | 0.0721 (14) | −0.0456 (13) | −0.0158 (11) | 0.0014 (12) |
F2B | 0.109 (2) | 0.157 (3) | 0.117 (2) | −0.089 (2) | 0.0587 (17) | −0.099 (2) |
F3B | 0.0739 (14) | 0.0757 (14) | 0.0837 (14) | −0.0487 (12) | 0.0104 (11) | 0.0088 (11) |
F4B | 0.0472 (10) | 0.0400 (9) | 0.0904 (13) | −0.0042 (7) | 0.0346 (9) | −0.0085 (8) |
F5B | 0.0679 (13) | 0.0311 (8) | 0.1054 (16) | −0.0032 (8) | 0.0319 (11) | −0.0196 (9) |
F6B | 0.0495 (10) | 0.0355 (8) | 0.0743 (12) | 0.0027 (7) | 0.0057 (9) | 0.0018 (8) |
O1B | 0.0177 (9) | 0.0292 (9) | 0.1087 (17) | −0.0001 (7) | 0.0179 (9) | −0.0146 (10) |
N1B | 0.0288 (10) | 0.0309 (10) | 0.0492 (12) | −0.0074 (8) | 0.0151 (9) | −0.0048 (9) |
N2B | 0.0140 (8) | 0.0239 (9) | 0.0475 (11) | −0.0008 (7) | 0.0072 (8) | −0.0026 (8) |
N3B | 0.0197 (9) | 0.0273 (9) | 0.0421 (11) | −0.0050 (7) | 0.0054 (8) | −0.0004 (8) |
C1B | 0.0224 (11) | 0.0239 (10) | 0.0436 (13) | 0.0035 (8) | 0.0113 (9) | −0.0010 (9) |
C2B | 0.0213 (11) | 0.0340 (12) | 0.0441 (13) | 0.0002 (9) | 0.0083 (9) | −0.0028 (10) |
C3B | 0.0341 (13) | 0.0216 (11) | 0.0552 (15) | −0.0009 (9) | 0.0185 (11) | −0.0001 (10) |
C4B | 0.0250 (11) | 0.0232 (11) | 0.0517 (14) | 0.0024 (9) | 0.0116 (10) | 0.0016 (10) |
C5B | 0.0199 (10) | 0.0219 (10) | 0.0446 (13) | −0.0003 (8) | 0.0135 (9) | −0.0011 (9) |
C6B | 0.0188 (11) | 0.0226 (10) | 0.0548 (14) | 0.0003 (8) | 0.0098 (10) | 0.0011 (10) |
C7B | 0.0221 (11) | 0.0294 (11) | 0.0411 (12) | −0.0028 (9) | 0.0094 (9) | −0.0010 (9) |
C8B | 0.0294 (12) | 0.0321 (12) | 0.0349 (12) | −0.0089 (9) | 0.0100 (9) | −0.0013 (9) |
C9B | 0.0284 (12) | 0.0429 (13) | 0.0355 (12) | −0.0084 (10) | 0.0091 (10) | −0.0034 (10) |
C10B | 0.0317 (13) | 0.0570 (17) | 0.0349 (13) | −0.0158 (12) | 0.0085 (10) | −0.0050 (11) |
C11B | 0.0447 (16) | 0.0560 (17) | 0.0330 (12) | −0.0245 (13) | 0.0118 (11) | −0.0063 (11) |
C12B | 0.0554 (17) | 0.0361 (13) | 0.0421 (14) | −0.0186 (12) | 0.0206 (12) | −0.0072 (11) |
C13B | 0.0402 (14) | 0.0325 (12) | 0.0407 (13) | −0.0098 (10) | 0.0157 (11) | −0.0028 (10) |
C14B | 0.062 (2) | 0.066 (2) | 0.0557 (18) | −0.0345 (17) | 0.0222 (17) | −0.0206 (16) |
C15B | 0.0508 (17) | 0.0283 (12) | 0.0659 (19) | −0.0044 (11) | 0.0207 (14) | −0.0073 (12) |
O1W | 0.119 (3) | 0.109 (3) | 0.134 (3) | 0.069 (2) | −0.006 (2) | −0.044 (2) |
F1A—C14A | 1.326 (4) | F2B—C14B | 1.306 (4) |
F2A—C14A | 1.331 (4) | F3B—C14B | 1.317 (4) |
F3A—C14A | 1.331 (3) | F4B—C15B | 1.339 (3) |
F4A—C15A | 1.330 (3) | F5B—C15B | 1.333 (3) |
F5A—C15A | 1.337 (3) | F6B—C15B | 1.341 (4) |
F6A—C15A | 1.338 (3) | O1B—C6B | 1.226 (3) |
O1A—C6A | 1.221 (3) | N1B—C2B | 1.331 (3) |
N1A—C2A | 1.331 (3) | N1B—C3B | 1.339 (3) |
N1A—C3A | 1.336 (3) | N2B—C6B | 1.343 (3) |
N2A—C6A | 1.352 (3) | N2B—N3B | 1.374 (3) |
N2A—N3A | 1.377 (2) | N2B—H2NB | 0.8600 |
N2A—H2NA | 0.8600 | N3B—C7B | 1.268 (3) |
N3A—C7A | 1.277 (3) | C1B—C2B | 1.381 (3) |
C1A—C5A | 1.385 (3) | C1B—C5B | 1.386 (3) |
C1A—C2A | 1.388 (3) | C1B—H1B | 0.9300 |
C1A—H1A | 0.9300 | C2B—H2B | 0.9300 |
C2A—H2A | 0.9300 | C3B—C4B | 1.380 (3) |
C3A—C4A | 1.379 (3) | C3B—H3B | 0.9300 |
C3A—H3A | 0.9300 | C4B—C5B | 1.385 (3) |
C4A—C5A | 1.382 (3) | C4B—H4B | 0.9300 |
C4A—H4A | 0.9300 | C5B—C6B | 1.490 (3) |
C5A—C6A | 1.496 (3) | C7B—C8B | 1.472 (3) |
C7A—C8A | 1.462 (3) | C7B—H7B | 0.9300 |
C7A—H7A | 0.9300 | C8B—C9B | 1.393 (4) |
C8A—C9A | 1.392 (3) | C8B—C13B | 1.399 (3) |
C8A—C13A | 1.401 (3) | C9B—C10B | 1.383 (3) |
C9A—C10A | 1.380 (3) | C9B—H9B | 0.9300 |
C9A—H9A | 0.9300 | C10B—C11B | 1.375 (4) |
C10A—C11A | 1.385 (3) | C10B—H10B | 0.9300 |
C10A—H10A | 0.9300 | C11B—C12B | 1.382 (4) |
C11A—C12A | 1.382 (3) | C11B—C14B | 1.506 (4) |
C11A—C14A | 1.493 (3) | C12B—C13B | 1.392 (4) |
C12A—C13A | 1.384 (3) | C12B—H12B | 0.9300 |
C12A—H12A | 0.9300 | C13B—C15B | 1.496 (4) |
C13A—C15A | 1.503 (3) | O1W—H1WA | 0.8400 |
F1B—C14B | 1.313 (5) | O1W—H1WB | 0.8400 |
C2A—N1A—C3A | 116.8 (2) | C6B—N2B—N3B | 116.85 (18) |
C6A—N2A—N3A | 118.29 (17) | C6B—N2B—H2NB | 121.6 |
C6A—N2A—H2NA | 120.9 | N3B—N2B—H2NB | 121.6 |
N3A—N2A—H2NA | 120.9 | C7B—N3B—N2B | 116.41 (19) |
C7A—N3A—N2A | 114.54 (18) | C2B—C1B—C5B | 118.1 (2) |
C5A—C1A—C2A | 118.9 (2) | C2B—C1B—H1B | 120.9 |
C5A—C1A—H1A | 120.5 | C5B—C1B—H1B | 120.9 |
C2A—C1A—H1A | 120.5 | N1B—C2B—C1B | 124.4 (2) |
N1A—C2A—C1A | 123.2 (2) | N1B—C2B—H2B | 117.8 |
N1A—C2A—H2A | 118.4 | C1B—C2B—H2B | 117.8 |
C1A—C2A—H2A | 118.4 | N1B—C3B—C4B | 123.3 (2) |
N1A—C3A—C4A | 124.3 (2) | N1B—C3B—H3B | 118.3 |
N1A—C3A—H3A | 117.8 | C4B—C3B—H3B | 118.3 |
C4A—C3A—H3A | 117.8 | C3B—C4B—C5B | 119.0 (2) |
C3A—C4A—C5A | 118.3 (2) | C3B—C4B—H4B | 120.5 |
C3A—C4A—H4A | 120.9 | C5B—C4B—H4B | 120.5 |
C5A—C4A—H4A | 120.9 | C4B—C5B—C1B | 118.4 (2) |
C4A—C5A—C1A | 118.4 (2) | C4B—C5B—C6B | 118.2 (2) |
C4A—C5A—C6A | 119.25 (19) | C1B—C5B—C6B | 123.4 (2) |
C1A—C5A—C6A | 122.32 (18) | O1B—C6B—N2B | 122.8 (2) |
O1A—C6A—N2A | 123.70 (19) | O1B—C6B—C5B | 120.0 (2) |
O1A—C6A—C5A | 121.77 (18) | N2B—C6B—C5B | 117.14 (19) |
N2A—C6A—C5A | 114.53 (18) | N3B—C7B—C8B | 118.0 (2) |
N3A—C7A—C8A | 119.11 (19) | N3B—C7B—H7B | 121.0 |
N3A—C7A—H7A | 120.4 | C8B—C7B—H7B | 121.0 |
C8A—C7A—H7A | 120.4 | C9B—C8B—C13B | 118.5 (2) |
C9A—C8A—C13A | 118.67 (19) | C9B—C8B—C7B | 119.4 (2) |
C9A—C8A—C7A | 119.81 (19) | C13B—C8B—C7B | 122.1 (2) |
C13A—C8A—C7A | 121.51 (19) | C10B—C9B—C8B | 121.3 (3) |
C10A—C9A—C8A | 121.3 (2) | C10B—C9B—H9B | 119.3 |
C10A—C9A—H9A | 119.4 | C8B—C9B—H9B | 119.3 |
C8A—C9A—H9A | 119.4 | C11B—C10B—C9B | 119.2 (3) |
C9A—C10A—C11A | 119.2 (2) | C11B—C10B—H10B | 120.4 |
C9A—C10A—H10A | 120.4 | C9B—C10B—H10B | 120.4 |
C11A—C10A—H10A | 120.4 | C10B—C11B—C12B | 121.1 (2) |
C12A—C11A—C10A | 120.8 (2) | C10B—C11B—C14B | 119.4 (3) |
C12A—C11A—C14A | 118.9 (2) | C12B—C11B—C14B | 119.4 (3) |
C10A—C11A—C14A | 120.3 (2) | C11B—C12B—C13B | 119.6 (3) |
C11A—C12A—C13A | 119.9 (2) | C11B—C12B—H12B | 120.2 |
C11A—C12A—H12A | 120.1 | C13B—C12B—H12B | 120.2 |
C13A—C12A—H12A | 120.1 | C12B—C13B—C8B | 120.2 (3) |
C12A—C13A—C8A | 120.2 (2) | C12B—C13B—C15B | 119.3 (2) |
C12A—C13A—C15A | 118.6 (2) | C8B—C13B—C15B | 120.5 (2) |
C8A—C13A—C15A | 121.20 (19) | F2B—C14B—F1B | 105.4 (3) |
F1A—C14A—F3A | 106.7 (2) | F2B—C14B—F3B | 108.0 (3) |
F1A—C14A—F2A | 106.6 (2) | F1B—C14B—F3B | 106.8 (3) |
F3A—C14A—F2A | 106.2 (2) | F2B—C14B—C11B | 111.3 (3) |
F1A—C14A—C11A | 112.5 (2) | F1B—C14B—C11B | 113.8 (3) |
F3A—C14A—C11A | 112.8 (2) | F3B—C14B—C11B | 111.2 (3) |
F2A—C14A—C11A | 111.6 (2) | F5B—C15B—F4B | 106.8 (2) |
F4A—C15A—F5A | 106.9 (2) | F5B—C15B—F6B | 106.3 (2) |
F4A—C15A—F6A | 106.45 (19) | F4B—C15B—F6B | 105.9 (2) |
F5A—C15A—F6A | 105.99 (19) | F5B—C15B—C13B | 112.7 (2) |
F4A—C15A—C13A | 112.60 (19) | F4B—C15B—C13B | 112.4 (2) |
F5A—C15A—C13A | 111.95 (19) | F6B—C15B—C13B | 112.2 (2) |
F6A—C15A—C13A | 112.5 (2) | H1WA—O1W—H1WB | 145.0 |
C2B—N1B—C3B | 116.7 (2) | ||
C6A—N2A—N3A—C7A | −175.0 (2) | C6B—N2B—N3B—C7B | −178.6 (2) |
C3A—N1A—C2A—C1A | 1.3 (4) | C3B—N1B—C2B—C1B | −1.3 (4) |
C5A—C1A—C2A—N1A | −1.7 (4) | C5B—C1B—C2B—N1B | 0.3 (4) |
C2A—N1A—C3A—C4A | 0.8 (4) | C2B—N1B—C3B—C4B | 0.6 (4) |
N1A—C3A—C4A—C5A | −2.4 (4) | N1B—C3B—C4B—C5B | 1.1 (4) |
C3A—C4A—C5A—C1A | 2.0 (3) | C3B—C4B—C5B—C1B | −2.1 (4) |
C3A—C4A—C5A—C6A | −179.5 (2) | C3B—C4B—C5B—C6B | 179.6 (2) |
C2A—C1A—C5A—C4A | −0.1 (3) | C2B—C1B—C5B—C4B | 1.4 (4) |
C2A—C1A—C5A—C6A | −178.6 (2) | C2B—C1B—C5B—C6B | 179.6 (2) |
N3A—N2A—C6A—O1A | 0.0 (3) | N3B—N2B—C6B—O1B | 0.6 (4) |
N3A—N2A—C6A—C5A | 179.77 (18) | N3B—N2B—C6B—C5B | 179.9 (2) |
C4A—C5A—C6A—O1A | −33.3 (3) | C4B—C5B—C6B—O1B | 29.3 (4) |
C1A—C5A—C6A—O1A | 145.2 (2) | C1B—C5B—C6B—O1B | −148.9 (3) |
C4A—C5A—C6A—N2A | 146.9 (2) | C4B—C5B—C6B—N2B | −150.0 (2) |
C1A—C5A—C6A—N2A | −34.6 (3) | C1B—C5B—C6B—N2B | 31.8 (4) |
N2A—N3A—C7A—C8A | −179.7 (2) | N2B—N3B—C7B—C8B | 179.5 (2) |
N3A—C7A—C8A—C9A | 12.0 (3) | N3B—C7B—C8B—C9B | −11.4 (3) |
N3A—C7A—C8A—C13A | −168.1 (2) | N3B—C7B—C8B—C13B | 167.7 (2) |
C13A—C8A—C9A—C10A | 1.1 (4) | C13B—C8B—C9B—C10B | −2.3 (4) |
C7A—C8A—C9A—C10A | −179.0 (2) | C7B—C8B—C9B—C10B | 176.9 (2) |
C8A—C9A—C10A—C11A | −0.1 (4) | C8B—C9B—C10B—C11B | 1.7 (4) |
C9A—C10A—C11A—C12A | −1.1 (4) | C9B—C10B—C11B—C12B | 0.3 (4) |
C9A—C10A—C11A—C14A | 177.1 (2) | C9B—C10B—C11B—C14B | −179.1 (3) |
C10A—C11A—C12A—C13A | 1.4 (4) | C10B—C11B—C12B—C13B | −1.5 (4) |
C14A—C11A—C12A—C13A | −176.8 (2) | C14B—C11B—C12B—C13B | 177.9 (3) |
C11A—C12A—C13A—C8A | −0.4 (4) | C11B—C12B—C13B—C8B | 0.8 (4) |
C11A—C12A—C13A—C15A | −180.0 (2) | C11B—C12B—C13B—C15B | −179.1 (3) |
C9A—C8A—C13A—C12A | −0.8 (3) | C9B—C8B—C13B—C12B | 1.0 (4) |
C7A—C8A—C13A—C12A | 179.2 (2) | C7B—C8B—C13B—C12B | −178.1 (2) |
C9A—C8A—C13A—C15A | 178.7 (2) | C9B—C8B—C13B—C15B | −179.0 (2) |
C7A—C8A—C13A—C15A | −1.2 (4) | C7B—C8B—C13B—C15B | 1.8 (4) |
C12A—C11A—C14A—F1A | −151.1 (2) | C10B—C11B—C14B—F2B | −142.1 (3) |
C10A—C11A—C14A—F1A | 30.6 (4) | C12B—C11B—C14B—F2B | 38.5 (4) |
C12A—C11A—C14A—F3A | −30.4 (4) | C10B—C11B—C14B—F1B | −23.1 (4) |
C10A—C11A—C14A—F3A | 151.4 (3) | C12B—C11B—C14B—F1B | 157.5 (3) |
C12A—C11A—C14A—F2A | 89.1 (3) | C10B—C11B—C14B—F3B | 97.5 (4) |
C10A—C11A—C14A—F2A | −89.1 (3) | C12B—C11B—C14B—F3B | −81.9 (4) |
C12A—C13A—C15A—F4A | −120.3 (2) | C12B—C13B—C15B—F5B | 0.8 (4) |
C8A—C13A—C15A—F4A | 60.1 (3) | C8B—C13B—C15B—F5B | −179.1 (2) |
C12A—C13A—C15A—F5A | 0.2 (3) | C12B—C13B—C15B—F4B | −120.0 (3) |
C8A—C13A—C15A—F5A | −179.4 (2) | C8B—C13B—C15B—F4B | 60.1 (3) |
C12A—C13A—C15A—F6A | 119.4 (2) | C12B—C13B—C15B—F6B | 120.8 (3) |
C8A—C13A—C15A—F6A | −60.2 (3) | C8B—C13B—C15B—F6B | −59.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···O1B | 0.86 | 2.05 | 2.856 (3) | 156 |
N2B—H2NB···O1Ai | 0.86 | 2.10 | 2.908 (3) | 155 |
C7A—H7A···O1B | 0.93 | 2.23 | 3.055 (3) | 147 |
C7B—H7B···O1Ai | 0.93 | 2.36 | 3.158 (3) | 144 |
C2B—H2B···F1Aii | 0.93 | 2.52 | 3.294 (3) | 141 |
C9A—H9A···F2Biii | 0.93 | 2.41 | 3.162 (4) | 138 |
C12B—H12B···O1Wiv | 0.93 | 2.58 | 3.408 (5) | 149 |
O1W—H1WA···F2Biv | 0.84 | 2.01 | 2.845 (5) | 180 |
O1W—H1WB···N1Bv | 0.84 | 2.09 | 2.932 (5) | 180 |
Symmetry codes: (i) x−1, y, z; (ii) x−2, −y+3/2, z−1/2; (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 formula | 2C15H9F6N3O·H2O |
Mr | 740.52 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 8.2487 (18), 26.649 (6), 14.779 (3) |
β (°) | 109.076 (10) |
V (Å3) | 3070.3 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.59 × 0.17 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.914, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29846, 7030, 5239 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.162, 1.02 |
No. of reflections | 7030 |
No. of parameters | 460 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.68 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···O1B | 0.86 | 2.05 | 2.856 (3) | 156 |
N2B—H2NB···O1Ai | 0.86 | 2.10 | 2.908 (3) | 155 |
C7A—H7A···O1B | 0.93 | 2.23 | 3.055 (3) | 147 |
C7B—H7B···O1Ai | 0.93 | 2.36 | 3.158 (3) | 144 |
C2B—H2B···F1Aii | 0.93 | 2.52 | 3.294 (3) | 141 |
C9A—H9A···F2Biii | 0.93 | 2.41 | 3.162 (4) | 138 |
C12B—H12B···O1Wiv | 0.93 | 2.58 | 3.408 (5) | 149 |
O1W—H1WA···F2Biv | 0.84 | 2.01 | 2.845 (5) | 180 |
O1W—H1WB···N1Bv | 0.84 | 2.09 | 2.932 (5) | 180 |
Symmetry codes: (i) x−1, y, z; (ii) x−2, −y+3/2, z−1/2; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+2, −z+1; (v) x+1, −y+3/2, z+1/2. |
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 C7A═N3A and C7B═N3B 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 π–π 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].