Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045552/dn3063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045552/dn3063Isup2.hkl |
CCDC reference: 663809
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.132
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for .................. CG1 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ? PLAT481_ALERT_4_C Long D...A H-Bond Reported N2 .. CG1 .. 3.94 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Domino et al. (1984); Li et al. (1998); Özçelik et al. (2004).
Phenylhydrazine (1 mmol, 0.108 g) was dissolved in anhydrous methanol, H2SO4 (98% 0.5 ml) was added to this, the mixture was stirred for several minitutes at 351 K, 2,4-dichlorobenzyaldehyde (1 mmol 0.175 g) in methanol (8 ml) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized in dichloromethane, brown single crystals of (I) was obtained after 5 d.
All H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H=0.93 Å and N—H= 0.86 Å with Uiso(H)=1.2Ueq(C,N).
The chemistry of hydrazones has been widely investigated in recent years, owning to their coordinating capability, pharmacological activity, antibacterial properties and their use in analytical chemistry as highly selective extractants (Domino et al., 1984; Li et al., 1998).
The title molecule crystallizes in the E conformation, with an N2—N1—C7—C1 torsion angle of 179.6 (2)°. The N1—N2 and N1=C7 bond distances are comparable to those in the related hydrazones derivates (Özçelik et al. 2004). There is more pronounced asymmetry in the exocyclic angles at C1 and C8. The dihedral angles between the two benzene ring is 6.70 (13)°, the dichlorophenyl ring make dihedral angle with the central hydrazone bridge (N2/N1/C7) of 6.49 (11)°, while the central hydrazone bridge is co-planar. with the phenyl ring
The molecules are linked by N—H···π interaction (Table 1).
For related literature, see: Domino et al. (1984); Li et al. (1998); Özçelik et al. (2004).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. Molecular view of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. |
C13H10Cl2N2 | F(000) = 1088 |
Mr = 265.13 | Dx = 1.401 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1225 reflections |
a = 16.074 (3) Å | θ = 2.5–24.1° |
b = 8.0870 (16) Å | µ = 0.49 mm−1 |
c = 19.333 (4) Å | T = 298 K |
V = 2513.1 (9) Å3 | Block, brown |
Z = 8 | 0.30 × 0.25 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 2599 independent reflections |
Radiation source: fine-focus sealed tube | 2395 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
Tmin = 0.908, Tmax = 0.908 | k = −10→8 |
15692 measured reflections | l = −22→24 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0417P)2 + 1.2232P] where P = (Fo2 + 2Fc2)/3 |
2599 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C13H10Cl2N2 | V = 2513.1 (9) Å3 |
Mr = 265.13 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.074 (3) Å | µ = 0.49 mm−1 |
b = 8.0870 (16) Å | T = 298 K |
c = 19.333 (4) Å | 0.30 × 0.25 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 2599 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2395 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.908 | Rint = 0.039 |
15692 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.22 | Δρmax = 0.28 e Å−3 |
2599 reflections | Δρmin = −0.26 e Å−3 |
154 parameters |
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 | Occ. (<1) | |
Cl1 | 0.30414 (6) | 0.64104 (12) | 0.50050 (4) | 0.0915 (3) | |
Cl2 | 0.36390 (6) | 0.12890 (10) | 0.33193 (4) | 0.0806 (3) | |
N1 | 0.49038 (12) | 0.4273 (2) | 0.63809 (10) | 0.0488 (5) | |
N2 | 0.50608 (13) | 0.5073 (3) | 0.69797 (10) | 0.0549 (5) | |
H2 | 0.4763 | 0.5911 | 0.7096 | 0.066* | |
C1 | 0.41639 (14) | 0.4009 (3) | 0.53262 (12) | 0.0466 (5) | |
C2 | 0.35838 (14) | 0.4587 (3) | 0.48464 (12) | 0.0503 (6) | |
C3 | 0.34205 (15) | 0.3774 (3) | 0.42305 (13) | 0.0546 (6) | |
H3 | 0.3028 | 0.4188 | 0.3922 | 0.066* | |
C4 | 0.38476 (16) | 0.2352 (3) | 0.40837 (13) | 0.0539 (6) | |
C5 | 0.44459 (19) | 0.1751 (3) | 0.45313 (14) | 0.0632 (7) | |
H5 | 0.4746 | 0.0804 | 0.4421 | 0.076* | |
C6 | 0.45912 (17) | 0.2577 (3) | 0.51431 (13) | 0.0580 (6) | |
H6 | 0.4990 | 0.2162 | 0.5445 | 0.070* | |
C7 | 0.43389 (15) | 0.4853 (3) | 0.59798 (12) | 0.0501 (6) | |
H7 | 0.4044 | 0.5798 | 0.6103 | 0.060* | |
C8 | 0.57047 (15) | 0.4544 (3) | 0.74095 (11) | 0.0479 (5) | |
C9 | 0.58364 (17) | 0.5361 (3) | 0.80344 (13) | 0.0602 (7) | |
H9 | 0.5495 | 0.6240 | 0.8160 | 0.072* | |
C10 | 0.64752 (19) | 0.4865 (4) | 0.84683 (14) | 0.0686 (8) | |
H10 | 0.6561 | 0.5421 | 0.8883 | 0.082* | |
C11 | 0.69857 (17) | 0.3561 (4) | 0.82948 (15) | 0.0663 (8) | |
H11 | 0.7414 | 0.3236 | 0.8588 | 0.080* | |
C12 | 0.68496 (16) | 0.2745 (4) | 0.76772 (14) | 0.0640 (7) | |
H12 | 0.7189 | 0.1859 | 0.7557 | 0.077* | |
C13 | 0.62166 (16) | 0.3221 (3) | 0.72330 (13) | 0.0546 (6) | |
H13 | 0.6134 | 0.2659 | 0.6819 | 0.066* | |
CG1 | 0.6345 | 0.4049 | 0.7853 | 0.010* | 0.00 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0915 (6) | 0.1023 (7) | 0.0807 (5) | 0.0577 (5) | −0.0167 (4) | −0.0143 (4) |
Cl2 | 0.0948 (6) | 0.0796 (5) | 0.0673 (5) | −0.0035 (4) | −0.0170 (4) | −0.0152 (4) |
N1 | 0.0540 (11) | 0.0473 (10) | 0.0452 (11) | 0.0003 (9) | 0.0038 (9) | 0.0036 (9) |
N2 | 0.0637 (12) | 0.0536 (11) | 0.0473 (11) | 0.0126 (10) | −0.0010 (9) | −0.0038 (9) |
C1 | 0.0452 (12) | 0.0473 (12) | 0.0473 (13) | −0.0006 (10) | 0.0037 (10) | 0.0079 (10) |
C2 | 0.0419 (12) | 0.0555 (14) | 0.0535 (14) | 0.0061 (10) | 0.0045 (10) | 0.0046 (11) |
C3 | 0.0421 (12) | 0.0691 (16) | 0.0528 (14) | 0.0010 (12) | −0.0036 (11) | 0.0080 (12) |
C4 | 0.0589 (14) | 0.0528 (14) | 0.0500 (13) | −0.0094 (12) | −0.0002 (11) | 0.0019 (11) |
C5 | 0.0787 (18) | 0.0467 (13) | 0.0642 (16) | 0.0103 (13) | −0.0102 (14) | −0.0012 (12) |
C6 | 0.0686 (16) | 0.0482 (13) | 0.0573 (15) | 0.0107 (12) | −0.0099 (12) | 0.0056 (11) |
C7 | 0.0514 (13) | 0.0491 (13) | 0.0497 (13) | 0.0071 (11) | 0.0061 (11) | 0.0047 (10) |
C8 | 0.0506 (13) | 0.0491 (12) | 0.0439 (12) | −0.0032 (11) | 0.0055 (10) | 0.0059 (10) |
C9 | 0.0683 (16) | 0.0602 (15) | 0.0521 (14) | 0.0004 (13) | 0.0036 (12) | −0.0047 (12) |
C10 | 0.0743 (18) | 0.0794 (19) | 0.0521 (15) | −0.0137 (16) | −0.0063 (14) | −0.0038 (14) |
C11 | 0.0558 (15) | 0.0811 (19) | 0.0619 (17) | −0.0080 (14) | −0.0077 (13) | 0.0158 (15) |
C12 | 0.0591 (15) | 0.0633 (16) | 0.0697 (17) | 0.0047 (13) | 0.0031 (13) | 0.0108 (14) |
C13 | 0.0588 (15) | 0.0555 (14) | 0.0495 (13) | 0.0025 (12) | 0.0040 (11) | 0.0000 (11) |
Cl1—C2 | 1.741 (2) | C6—H6 | 0.9300 |
Cl2—C4 | 1.742 (3) | C7—H7 | 0.9300 |
N1—C7 | 1.283 (3) | C8—C13 | 1.392 (3) |
N1—N2 | 1.350 (3) | C8—C9 | 1.393 (3) |
N2—C8 | 1.395 (3) | C8—CG1 | 1.397 (2) |
N2—H2 | 0.8600 | C9—C10 | 1.385 (4) |
C1—C6 | 1.392 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.396 (3) | C10—C11 | 1.377 (4) |
C1—C7 | 1.463 (3) | C10—H10 | 0.9300 |
C2—C3 | 1.385 (3) | C11—C12 | 1.382 (4) |
C3—C4 | 1.369 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.386 (4) |
C4—C5 | 1.382 (4) | C12—H12 | 0.9300 |
C5—C6 | 1.378 (4) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | ||
C7—N1—N2 | 118.4 (2) | N1—C7—H7 | 120.4 |
N1—N2—C8 | 120.2 (2) | C1—C7—H7 | 120.4 |
N1—N2—H2 | 119.9 | C13—C8—C9 | 119.2 (2) |
C8—N2—H2 | 119.9 | C13—C8—N2 | 121.9 (2) |
C6—C1—C2 | 116.0 (2) | C9—C8—N2 | 118.9 (2) |
C6—C1—C7 | 120.9 (2) | C13—C8—CG1 | 59.69 (14) |
C2—C1—C7 | 123.1 (2) | C9—C8—CG1 | 59.47 (15) |
C3—C2—C1 | 122.6 (2) | N2—C8—CG1 | 178.4 (2) |
C3—C2—Cl1 | 117.29 (18) | C10—C9—C8 | 120.0 (3) |
C1—C2—Cl1 | 120.08 (19) | C10—C9—H9 | 120.0 |
C4—C3—C2 | 118.8 (2) | C8—C9—H9 | 120.0 |
C4—C3—H3 | 120.6 | C11—C10—C9 | 121.1 (3) |
C2—C3—H3 | 120.6 | C11—C10—H10 | 119.5 |
C3—C4—C5 | 121.0 (2) | C9—C10—H10 | 119.5 |
C3—C4—Cl2 | 119.6 (2) | C10—C11—C12 | 118.8 (3) |
C5—C4—Cl2 | 119.4 (2) | C10—C11—H11 | 120.6 |
C6—C5—C4 | 119.0 (2) | C12—C11—H11 | 120.6 |
C6—C5—H5 | 120.5 | C11—C12—C13 | 121.3 (3) |
C4—C5—H5 | 120.5 | C11—C12—H12 | 119.4 |
C5—C6—C1 | 122.5 (2) | C13—C12—H12 | 119.4 |
C5—C6—H6 | 118.7 | C12—C13—C8 | 119.7 (2) |
C1—C6—H6 | 118.7 | C12—C13—H13 | 120.1 |
N1—C7—C1 | 119.2 (2) | C8—C13—H13 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cg1i | 0.86 | 3.10 | 3.943 (2) | 167 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H10Cl2N2 |
Mr | 265.13 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 16.074 (3), 8.0870 (16), 19.333 (4) |
V (Å3) | 2513.1 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.30 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.908, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15692, 2599, 2395 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.132, 1.22 |
No. of reflections | 2599 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.26 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cg1i | 0.86 | 3.10 | 3.943 (2) | 166.6 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
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The chemistry of hydrazones has been widely investigated in recent years, owning to their coordinating capability, pharmacological activity, antibacterial properties and their use in analytical chemistry as highly selective extractants (Domino et al., 1984; Li et al., 1998).
The title molecule crystallizes in the E conformation, with an N2—N1—C7—C1 torsion angle of 179.6 (2)°. The N1—N2 and N1=C7 bond distances are comparable to those in the related hydrazones derivates (Özçelik et al. 2004). There is more pronounced asymmetry in the exocyclic angles at C1 and C8. The dihedral angles between the two benzene ring is 6.70 (13)°, the dichlorophenyl ring make dihedral angle with the central hydrazone bridge (N2/N1/C7) of 6.49 (11)°, while the central hydrazone bridge is co-planar. with the phenyl ring
The molecules are linked by N—H···π interaction (Table 1).