Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043590/pk2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043590/pk2040Isup2.hkl |
CCDC reference: 663738
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.150
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT414_ALERT_2_C Short Intra D-H..H-X H20 .. H21 .. 1.97 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H21 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.01 mol, 2.32 g) was added. The reaction mixture was refluxed for 6 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 81%). The compound (1.0 mmol,0.38 g) was dissolved in dimethylformamide (20 ml) and kept at room temperature for 45 d to obtain yellow single crystals suitable for X-ray diffraction.
All H atoms were positioned geometrically and treated as riding on their parent atoms, with CMe—H = 0.96 Å, CAr—H = 0.93 Å, O—H = 0.82 Å, and N—H = 0.86 Å and with Uiso(H) = 1.5Ueq(CMe, O) and 1.2Ueq(CAr, N).
The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.
The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The three benzene rings, C1—C6 (A), C8—C13 (B) and C15—C20 (C), make dihedral angles of 74.21 (7) ° (A/B), 79.58 (7) ° (B/C) and 16.85 (12) ° (A/C). The crystal structure is stabilized by intramolecular N—H···O and intermolecular C—H···O hydrogen bonds (Table 1. and Fig. 2).
For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998); Singh et al. (1982).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C21H17ClN2O3 | F(000) = 792 |
Mr = 380.82 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3423 reflections |
a = 9.2861 (19) Å | θ = 2.4–21.3° |
b = 13.026 (3) Å | µ = 0.23 mm−1 |
c = 15.722 (3) Å | T = 273 K |
β = 102.089 (8)° | Plate, yellow |
V = 1859.6 (7) Å3 | 0.33 × 0.24 × 0.13 mm |
Z = 4 |
Bruker APEX II CCD area-detector diffractometer | 3259 independent reflections |
Radiation source: fine-focus sealed tube | 2262 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→11 |
Tmin = 0.945, Tmax = 0.966 | k = −15→15 |
16781 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0962P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3259 reflections | Δρmax = 0.20 e Å−3 |
247 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (3) |
C21H17ClN2O3 | V = 1859.6 (7) Å3 |
Mr = 380.82 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2861 (19) Å | µ = 0.23 mm−1 |
b = 13.026 (3) Å | T = 273 K |
c = 15.722 (3) Å | 0.33 × 0.24 × 0.13 mm |
β = 102.089 (8)° |
Bruker APEX II CCD area-detector diffractometer | 3259 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2262 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.966 | Rint = 0.045 |
16781 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.20 e Å−3 |
3259 reflections | Δρmin = −0.26 e Å−3 |
247 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 > 2σ(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 | ||
Cl1 | 0.13352 (7) | 0.88139 (5) | 0.18144 (5) | 0.0801 (3) | |
O1 | 0.6354 (2) | 0.60874 (13) | 0.30330 (11) | 0.0705 (5) | |
H1 | 0.6975 | 0.6134 | 0.2733 | 0.106* | |
O2 | 0.99011 (18) | 0.55710 (13) | 0.21902 (10) | 0.0674 (5) | |
O3 | 1.35103 (16) | 0.55585 (13) | −0.08113 (10) | 0.0647 (5) | |
N1 | 0.74992 (19) | 0.67796 (14) | 0.17801 (11) | 0.0530 (5) | |
N2 | 0.85754 (19) | 0.67454 (14) | 0.13064 (12) | 0.0566 (5) | |
H21 | 0.8526 | 0.7146 | 0.0866 | 0.068* | |
C1 | 0.2845 (2) | 0.80152 (17) | 0.21698 (15) | 0.0570 (6) | |
C2 | 0.3986 (2) | 0.80150 (16) | 0.17394 (14) | 0.0533 (5) | |
H2 | 0.3948 | 0.8449 | 0.1266 | 0.064* | |
C3 | 0.5204 (2) | 0.73755 (15) | 0.19997 (13) | 0.0471 (5) | |
C4 | 0.5222 (3) | 0.67327 (16) | 0.27222 (14) | 0.0538 (5) | |
C5 | 0.4053 (3) | 0.67538 (19) | 0.31437 (15) | 0.0643 (7) | |
H5 | 0.4074 | 0.6327 | 0.3620 | 0.077* | |
C6 | 0.2874 (3) | 0.7384 (2) | 0.28777 (15) | 0.0664 (7) | |
H6 | 0.2100 | 0.7388 | 0.3169 | 0.080* | |
C7 | 0.6397 (2) | 0.73889 (16) | 0.15167 (13) | 0.0473 (5) | |
C8 | 0.6309 (2) | 0.80770 (15) | 0.07446 (13) | 0.0458 (5) | |
C9 | 0.7175 (2) | 0.89464 (16) | 0.07990 (14) | 0.0557 (6) | |
H9 | 0.7789 | 0.9121 | 0.1325 | 0.067* | |
C10 | 0.7133 (3) | 0.95584 (18) | 0.00764 (15) | 0.0643 (6) | |
H10 | 0.7722 | 1.0141 | 0.0119 | 0.077* | |
C11 | 0.6227 (3) | 0.93109 (18) | −0.07028 (15) | 0.0612 (6) | |
H11 | 0.6207 | 0.9719 | −0.1190 | 0.073* | |
C12 | 0.5354 (3) | 0.8458 (2) | −0.07564 (15) | 0.0643 (6) | |
H12 | 0.4728 | 0.8294 | −0.1282 | 0.077* | |
C13 | 0.5392 (2) | 0.78388 (18) | −0.00424 (13) | 0.0585 (6) | |
H13 | 0.4798 | 0.7258 | −0.0090 | 0.070* | |
C14 | 0.9726 (2) | 0.60810 (16) | 0.15275 (13) | 0.0492 (5) | |
C15 | 1.0706 (2) | 0.60199 (15) | 0.08952 (13) | 0.0472 (5) | |
C16 | 1.1987 (2) | 0.54446 (18) | 0.11171 (15) | 0.0592 (6) | |
H16 | 1.2230 | 0.5141 | 0.1664 | 0.071* | |
C17 | 1.2902 (2) | 0.53153 (19) | 0.05433 (15) | 0.0626 (6) | |
H17 | 1.3764 | 0.4936 | 0.0707 | 0.075* | |
C18 | 1.2549 (2) | 0.57464 (17) | −0.02765 (13) | 0.0504 (5) | |
C19 | 1.1298 (2) | 0.63223 (18) | −0.05077 (14) | 0.0603 (6) | |
H19 | 1.1059 | 0.6625 | −0.1055 | 0.072* | |
C20 | 1.0394 (3) | 0.64517 (19) | 0.00765 (15) | 0.0605 (6) | |
H20 | 0.9544 | 0.6844 | −0.0087 | 0.073* | |
C21 | 1.3176 (3) | 0.5988 (2) | −0.16640 (15) | 0.0705 (7) | |
H21A | 1.2245 | 0.5729 | −0.1973 | 0.106* | |
H21B | 1.3931 | 0.5803 | −0.1969 | 0.106* | |
H21C | 1.3126 | 0.6722 | −0.1624 | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0543 (4) | 0.0815 (5) | 0.1113 (6) | 0.0072 (3) | 0.0332 (4) | −0.0043 (4) |
O1 | 0.0758 (12) | 0.0759 (12) | 0.0649 (11) | 0.0089 (9) | 0.0260 (9) | 0.0189 (8) |
O2 | 0.0651 (10) | 0.0873 (12) | 0.0523 (9) | 0.0141 (9) | 0.0184 (7) | 0.0135 (8) |
O3 | 0.0530 (9) | 0.0840 (12) | 0.0633 (10) | 0.0063 (8) | 0.0263 (8) | −0.0002 (8) |
N1 | 0.0519 (10) | 0.0576 (11) | 0.0548 (10) | 0.0021 (9) | 0.0232 (8) | −0.0006 (8) |
N2 | 0.0537 (11) | 0.0623 (12) | 0.0605 (11) | 0.0105 (9) | 0.0269 (9) | 0.0088 (9) |
C1 | 0.0490 (13) | 0.0548 (13) | 0.0726 (15) | −0.0083 (10) | 0.0250 (11) | −0.0100 (11) |
C2 | 0.0540 (13) | 0.0506 (13) | 0.0604 (13) | −0.0049 (10) | 0.0240 (10) | −0.0018 (10) |
C3 | 0.0490 (12) | 0.0449 (11) | 0.0510 (11) | −0.0057 (9) | 0.0186 (9) | −0.0040 (9) |
C4 | 0.0599 (13) | 0.0514 (13) | 0.0534 (12) | −0.0057 (11) | 0.0194 (10) | −0.0013 (10) |
C5 | 0.0748 (16) | 0.0673 (16) | 0.0582 (14) | −0.0141 (13) | 0.0310 (12) | 0.0019 (11) |
C6 | 0.0611 (15) | 0.0736 (16) | 0.0737 (16) | −0.0130 (13) | 0.0355 (12) | −0.0107 (13) |
C7 | 0.0471 (12) | 0.0481 (12) | 0.0497 (11) | −0.0017 (10) | 0.0166 (9) | −0.0045 (9) |
C8 | 0.0418 (11) | 0.0497 (12) | 0.0508 (12) | 0.0022 (9) | 0.0212 (9) | −0.0018 (9) |
C9 | 0.0558 (13) | 0.0575 (14) | 0.0541 (13) | −0.0076 (11) | 0.0125 (10) | −0.0019 (10) |
C10 | 0.0713 (16) | 0.0550 (14) | 0.0705 (16) | −0.0094 (12) | 0.0237 (12) | 0.0038 (11) |
C11 | 0.0741 (16) | 0.0592 (14) | 0.0554 (13) | 0.0080 (13) | 0.0252 (12) | 0.0065 (11) |
C12 | 0.0650 (15) | 0.0789 (16) | 0.0495 (13) | −0.0035 (13) | 0.0131 (11) | −0.0033 (11) |
C13 | 0.0601 (14) | 0.0641 (14) | 0.0528 (13) | −0.0151 (12) | 0.0155 (11) | −0.0056 (11) |
C14 | 0.0452 (12) | 0.0560 (13) | 0.0465 (12) | −0.0004 (10) | 0.0094 (9) | −0.0022 (9) |
C15 | 0.0423 (11) | 0.0502 (12) | 0.0497 (12) | −0.0001 (9) | 0.0107 (9) | −0.0020 (9) |
C16 | 0.0525 (13) | 0.0745 (15) | 0.0511 (12) | 0.0092 (12) | 0.0122 (10) | 0.0092 (11) |
C17 | 0.0461 (12) | 0.0785 (16) | 0.0637 (14) | 0.0166 (12) | 0.0123 (10) | 0.0070 (12) |
C18 | 0.0432 (12) | 0.0554 (13) | 0.0547 (13) | −0.0034 (10) | 0.0153 (10) | −0.0045 (10) |
C19 | 0.0583 (14) | 0.0733 (15) | 0.0533 (13) | 0.0133 (12) | 0.0205 (11) | 0.0111 (11) |
C20 | 0.0563 (13) | 0.0699 (15) | 0.0580 (13) | 0.0215 (12) | 0.0180 (11) | 0.0119 (11) |
C21 | 0.0718 (16) | 0.0882 (18) | 0.0580 (15) | −0.0049 (14) | 0.0285 (12) | −0.0033 (12) |
Cl1—C1 | 1.741 (2) | C9—C10 | 1.382 (3) |
O1—C4 | 1.355 (3) | C9—H9 | 0.9300 |
O1—H1 | 0.8200 | C10—C11 | 1.371 (3) |
O2—C14 | 1.217 (2) | C10—H10 | 0.9300 |
O3—C18 | 1.371 (3) | C11—C12 | 1.368 (3) |
O3—C21 | 1.426 (3) | C11—H11 | 0.9300 |
N1—C7 | 1.293 (3) | C12—C13 | 1.377 (3) |
N1—N2 | 1.367 (2) | C12—H12 | 0.9300 |
N2—C14 | 1.362 (3) | C13—H13 | 0.9300 |
N2—H21 | 0.8600 | C14—C15 | 1.484 (3) |
C1—C2 | 1.372 (3) | C15—C20 | 1.379 (3) |
C1—C6 | 1.379 (3) | C15—C16 | 1.387 (3) |
C2—C3 | 1.395 (3) | C16—C17 | 1.373 (3) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.409 (3) | C17—C18 | 1.381 (3) |
C3—C7 | 1.468 (3) | C17—H17 | 0.9300 |
C4—C5 | 1.385 (3) | C18—C19 | 1.366 (3) |
C5—C6 | 1.362 (3) | C19—C20 | 1.378 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.497 (3) | C21—H21A | 0.9600 |
C8—C9 | 1.381 (3) | C21—H21B | 0.9600 |
C8—C13 | 1.382 (3) | C21—H21C | 0.9600 |
C4—O1—H1 | 109.5 | C12—C11—C10 | 119.4 (2) |
C18—O3—C21 | 117.72 (18) | C12—C11—H11 | 120.3 |
C7—N1—N2 | 117.75 (17) | C10—C11—H11 | 120.3 |
C14—N2—N1 | 120.38 (17) | C11—C12—C13 | 120.8 (2) |
C14—N2—H21 | 119.8 | C11—C12—H12 | 119.6 |
N1—N2—H21 | 119.8 | C13—C12—H12 | 119.6 |
C2—C1—C6 | 120.7 (2) | C12—C13—C8 | 120.3 (2) |
C2—C1—Cl1 | 119.68 (19) | C12—C13—H13 | 119.9 |
C6—C1—Cl1 | 119.60 (17) | C8—C13—H13 | 119.9 |
C1—C2—C3 | 121.2 (2) | O2—C14—N2 | 121.46 (19) |
C1—C2—H2 | 119.4 | O2—C14—C15 | 123.61 (19) |
C3—C2—H2 | 119.4 | N2—C14—C15 | 114.92 (18) |
C2—C3—C4 | 117.59 (19) | C20—C15—C16 | 117.21 (19) |
C2—C3—C7 | 119.61 (18) | C20—C15—C14 | 124.38 (19) |
C4—C3—C7 | 122.79 (19) | C16—C15—C14 | 118.31 (18) |
O1—C4—C5 | 117.8 (2) | C17—C16—C15 | 121.1 (2) |
O1—C4—C3 | 122.5 (2) | C17—C16—H16 | 119.4 |
C5—C4—C3 | 119.7 (2) | C15—C16—H16 | 119.4 |
C6—C5—C4 | 121.7 (2) | C16—C17—C18 | 120.3 (2) |
C6—C5—H5 | 119.2 | C16—C17—H17 | 119.8 |
C4—C5—H5 | 119.2 | C18—C17—H17 | 119.8 |
C5—C6—C1 | 119.1 (2) | C19—C18—O3 | 124.16 (19) |
C5—C6—H6 | 120.5 | C19—C18—C17 | 119.6 (2) |
C1—C6—H6 | 120.5 | O3—C18—C17 | 116.23 (19) |
N1—C7—C3 | 117.34 (18) | C18—C19—C20 | 119.5 (2) |
N1—C7—C8 | 122.16 (18) | C18—C19—H19 | 120.2 |
C3—C7—C8 | 120.49 (18) | C20—C19—H19 | 120.2 |
C9—C8—C13 | 118.7 (2) | C19—C20—C15 | 122.2 (2) |
C9—C8—C7 | 120.57 (18) | C19—C20—H20 | 118.9 |
C13—C8—C7 | 120.66 (18) | C15—C20—H20 | 118.9 |
C8—C9—C10 | 120.4 (2) | O3—C21—H21A | 109.5 |
C8—C9—H9 | 119.8 | O3—C21—H21B | 109.5 |
C10—C9—H9 | 119.8 | H21A—C21—H21B | 109.5 |
C11—C10—C9 | 120.3 (2) | O3—C21—H21C | 109.5 |
C11—C10—H10 | 119.8 | H21A—C21—H21C | 109.5 |
C9—C10—H10 | 119.8 | H21B—C21—H21C | 109.5 |
C7—N1—N2—C14 | −176.75 (18) | C7—C8—C9—C10 | 177.5 (2) |
C6—C1—C2—C3 | 0.4 (3) | C8—C9—C10—C11 | 0.2 (3) |
Cl1—C1—C2—C3 | −179.18 (15) | C9—C10—C11—C12 | 0.6 (4) |
C1—C2—C3—C4 | −0.2 (3) | C10—C11—C12—C13 | −1.0 (4) |
C1—C2—C3—C7 | 179.33 (19) | C11—C12—C13—C8 | 0.5 (4) |
C2—C3—C4—O1 | −179.54 (18) | C9—C8—C13—C12 | 0.3 (3) |
C7—C3—C4—O1 | 0.9 (3) | C7—C8—C13—C12 | −177.8 (2) |
C2—C3—C4—C5 | 0.0 (3) | N1—N2—C14—O2 | −6.7 (3) |
C7—C3—C4—C5 | −179.49 (19) | N1—N2—C14—C15 | 172.13 (17) |
O1—C4—C5—C6 | 179.6 (2) | O2—C14—C15—C20 | 168.4 (2) |
C3—C4—C5—C6 | 0.0 (3) | N2—C14—C15—C20 | −10.5 (3) |
C4—C5—C6—C1 | 0.1 (4) | O2—C14—C15—C16 | −7.9 (3) |
C2—C1—C6—C5 | −0.3 (3) | N2—C14—C15—C16 | 173.28 (18) |
Cl1—C1—C6—C5 | 179.25 (17) | C20—C15—C16—C17 | 0.1 (3) |
N2—N1—C7—C3 | 176.48 (17) | C14—C15—C16—C17 | 176.7 (2) |
N2—N1—C7—C8 | −2.7 (3) | C15—C16—C17—C18 | −1.0 (4) |
C2—C3—C7—N1 | −179.70 (18) | C21—O3—C18—C19 | −0.3 (3) |
C4—C3—C7—N1 | −0.2 (3) | C21—O3—C18—C17 | 179.7 (2) |
C2—C3—C7—C8 | −0.5 (3) | C16—C17—C18—C19 | 1.4 (4) |
C4—C3—C7—C8 | 179.07 (18) | C16—C17—C18—O3 | −178.6 (2) |
N1—C7—C8—C9 | −74.2 (3) | O3—C18—C19—C20 | 179.1 (2) |
C3—C7—C8—C9 | 106.6 (2) | C17—C18—C19—C20 | −1.0 (3) |
N1—C7—C8—C13 | 103.9 (2) | C18—C19—C20—C15 | 0.1 (4) |
C3—C7—C8—C13 | −75.3 (3) | C16—C15—C20—C19 | 0.3 (4) |
C13—C8—C9—C10 | −0.7 (3) | C14—C15—C20—C19 | −176.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.87 | 2.589 (2) | 146 |
C11—H11···O2i | 0.93 | 2.60 | 3.287 (3) | 130 |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H17ClN2O3 |
Mr | 380.82 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 9.2861 (19), 13.026 (3), 15.722 (3) |
β (°) | 102.089 (8) |
V (Å3) | 1859.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.33 × 0.24 × 0.13 |
Data collection | |
Diffractometer | Bruker APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.945, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16781, 3259, 2262 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.150, 1.00 |
No. of reflections | 3259 |
No. of parameters | 247 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.87 | 2.589 (2) | 145.7 |
C11—H11···O2i | 0.93 | 2.60 | 3.287 (3) | 130.3 |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.
The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The three benzene rings, C1—C6 (A), C8—C13 (B) and C15—C20 (C), make dihedral angles of 74.21 (7) ° (A/B), 79.58 (7) ° (B/C) and 16.85 (12) ° (A/C). The crystal structure is stabilized by intramolecular N—H···O and intermolecular C—H···O hydrogen bonds (Table 1. and Fig. 2).