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The amine N atom of the isatin portion of the title compound (systematic name: 2-oxo-2,3-dihydro-1H-indole-3-carbaldehyde benzoylhydrazone), C15H11N3O2, forms a hydrogen bond with the amide O atom of the benzoylhydrazone portion of a symmetry-related molecule to give rise to a hydrogen-bonded chain structure that propagates by a twofold screw axis along the a axis of the orthorhombic unit cell.
Supporting information
CCDC reference: 287473
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.058
- wR factor = 0.191
- Data-to-parameter ratio = 8.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact H4 .. H12 .. 2.05 Ang.
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
Yellowish
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.97 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT414_ALERT_2_C Short Intra D-H..H-X H1N .. H6 .. 1.96 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.10
From the CIF: _reflns_number_total 1463
Count of symmetry unique reflns 1474
Completeness (_total/calc) 99.25%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Isatin 3-benzoylhydrazone (0.50 g, 1.9 mmol) and zinc acetate (0.20 g, 0.9 mmol) were refluxed for 5 h. The yellow solid that precipitated was collected and recrystallized from pyridine to give yellow–orange blocks. The color is distinctly different from that of the monoclinic polymorph.
The phenyl ring comprising atoms C1–C6 was refined with the C—C distances restrained to 1.390 (5) Å; the 1,4-distances were restrained to 2.780 (5) Å. As there are no heavy scatterers, Friedel pairs were merged. H atoms were placed at calculated positions (C—H = 0.93 Å and N—H = 0.86 Å) and were included in the refinement in the riding-model approximation, with Uiso(H) set to 1.2Ueq(C,N).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-oxo-2,3-dihydro-1
H-indole-3-carbaldehyde benzoylhydrazone
top
Crystal data top
C15H11N3O2 | F(000) = 552 |
Mr = 265.27 | Dx = 1.467 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 928 reflections |
a = 8.0023 (9) Å | θ = 2.5–25.7° |
b = 28.549 (3) Å | µ = 0.10 mm−1 |
c = 5.2574 (6) Å | T = 295 K |
V = 1201.1 (2) Å3 | Block, yellow–orange |
Z = 4 | 0.34 × 0.21 × 0.15 mm |
Data collection top
Bruker SMART area-detector diffractometer | 1176 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.1°, θmin = 1.4° |
ϕ and ω scan | h = −8→10 |
6999 measured reflections | k = −36→36 |
1463 independent reflections | l = −6→5 |
Refinement top
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.1317P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1463 reflections | Δρmax = 0.53 e Å−3 |
181 parameters | Δρmin = −0.29 e Å−3 |
10 restraints | Absolute structure: Flack parameter not calculated. |
Primary atom site location: structure-invariant direct methods | |
Crystal data top
C15H11N3O2 | V = 1201.1 (2) Å3 |
Mr = 265.27 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 8.0023 (9) Å | µ = 0.10 mm−1 |
b = 28.549 (3) Å | T = 295 K |
c = 5.2574 (6) Å | 0.34 × 0.21 × 0.15 mm |
Data collection top
Bruker SMART area-detector diffractometer | 1176 reflections with I > 2σ(I) |
6999 measured reflections | Rint = 0.033 |
1463 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 10 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.53 e Å−3 |
1463 reflections | Δρmin = −0.29 e Å−3 |
181 parameters | Absolute structure: Flack parameter not calculated. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.9079 (4) | 0.64394 (9) | 0.5000 (9) | 0.0551 (9) | |
O2 | 0.5986 (4) | 0.71442 (10) | 1.2189 (9) | 0.0499 (8) | |
N1 | 0.7807 (4) | 0.67794 (11) | 0.8348 (10) | 0.0419 (8) | |
H1n | 0.7250 | 0.6740 | 0.9730 | 0.050* | |
N2 | 0.8179 (4) | 0.72247 (11) | 0.7520 (9) | 0.0399 (8) | |
N3 | 0.6094 (4) | 0.79527 (11) | 1.1946 (9) | 0.0419 (8) | |
H3n | 0.5486 | 0.8023 | 1.3239 | 0.050* | |
C1 | 0.7871 (5) | 0.59389 (11) | 0.8110 (8) | 0.0451 (11) | |
C2 | 0.8561 (6) | 0.55486 (12) | 0.6924 (7) | 0.0629 (14) | |
H2 | 0.9284 | 0.5584 | 0.5552 | 0.075* | |
C3 | 0.8157 (7) | 0.51022 (13) | 0.7820 (10) | 0.085 (2) | |
H3 | 0.8590 | 0.4839 | 0.7010 | 0.102* | |
C4 | 0.7118 (6) | 0.50472 (12) | 0.9899 (10) | 0.0667 (16) | |
H4 | 0.6873 | 0.4749 | 1.0502 | 0.080* | |
C5 | 0.6448 (6) | 0.54334 (14) | 1.1072 (7) | 0.0759 (18) | |
H5 | 0.5736 | 0.5394 | 1.2454 | 0.091* | |
C6 | 0.6823 (6) | 0.58848 (12) | 1.0217 (10) | 0.0582 (12) | |
H6 | 0.6382 | 0.6145 | 1.1038 | 0.070* | |
C7 | 0.8314 (5) | 0.64071 (13) | 0.6995 (11) | 0.0396 (10) | |
C8 | 0.7545 (5) | 0.75561 (12) | 0.8866 (10) | 0.0350 (9) | |
C9 | 0.6446 (5) | 0.75100 (14) | 1.1214 (10) | 0.0390 (9) | |
C10 | 0.6841 (4) | 0.82823 (12) | 1.0342 (11) | 0.0363 (8) | |
C11 | 0.6762 (5) | 0.87673 (14) | 1.0456 (12) | 0.0456 (10) | |
H11 | 0.6189 | 0.8920 | 1.1753 | 0.055* | |
C12 | 0.7573 (6) | 0.90155 (14) | 0.8557 (12) | 0.0494 (11) | |
H12 | 0.7518 | 0.9341 | 0.8571 | 0.059* | |
C13 | 0.8460 (5) | 0.87959 (13) | 0.6644 (11) | 0.0458 (10) | |
H13 | 0.8986 | 0.8974 | 0.5397 | 0.055* | |
C14 | 0.8569 (4) | 0.83080 (13) | 0.6578 (11) | 0.0417 (10) | |
H14 | 0.9188 | 0.8157 | 0.5326 | 0.050* | |
C15 | 0.7734 (5) | 0.80574 (13) | 0.8417 (10) | 0.0374 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.073 (2) | 0.0388 (15) | 0.053 (2) | −0.0012 (14) | 0.0181 (18) | −0.0018 (15) |
O2 | 0.0633 (18) | 0.0391 (14) | 0.0474 (19) | −0.0043 (12) | 0.0125 (17) | 0.0069 (14) |
N1 | 0.0498 (17) | 0.0287 (15) | 0.047 (2) | −0.0036 (13) | 0.0079 (17) | 0.0020 (16) |
N2 | 0.0459 (17) | 0.0290 (15) | 0.045 (2) | −0.0013 (13) | 0.0022 (16) | −0.0018 (15) |
N3 | 0.0535 (19) | 0.0367 (16) | 0.035 (2) | 0.0060 (13) | 0.0046 (17) | −0.0025 (15) |
C1 | 0.046 (2) | 0.034 (2) | 0.056 (3) | −0.0049 (16) | −0.005 (2) | 0.001 (2) |
C2 | 0.081 (3) | 0.037 (2) | 0.071 (4) | 0.000 (2) | −0.001 (3) | −0.005 (3) |
C3 | 0.127 (5) | 0.033 (2) | 0.096 (6) | 0.002 (3) | −0.028 (5) | 0.003 (3) |
C4 | 0.090 (3) | 0.029 (2) | 0.081 (4) | −0.015 (2) | −0.024 (4) | 0.018 (3) |
C5 | 0.085 (4) | 0.062 (3) | 0.081 (5) | −0.023 (3) | −0.006 (3) | 0.024 (3) |
C6 | 0.061 (3) | 0.044 (2) | 0.069 (3) | −0.006 (2) | 0.001 (3) | 0.011 (3) |
C7 | 0.0409 (19) | 0.0311 (18) | 0.047 (3) | −0.0011 (14) | −0.001 (2) | 0.0017 (18) |
C8 | 0.0385 (18) | 0.0281 (17) | 0.038 (2) | −0.0004 (15) | 0.0001 (18) | −0.0014 (18) |
C9 | 0.043 (2) | 0.0364 (18) | 0.038 (2) | 0.0016 (16) | 0.0020 (18) | 0.0003 (17) |
C10 | 0.0410 (18) | 0.0308 (17) | 0.037 (2) | −0.0006 (15) | −0.0051 (18) | −0.0033 (18) |
C11 | 0.054 (2) | 0.0359 (19) | 0.047 (3) | 0.0062 (17) | −0.002 (2) | −0.004 (2) |
C12 | 0.059 (2) | 0.0331 (19) | 0.056 (3) | −0.0010 (18) | −0.004 (2) | 0.000 (2) |
C13 | 0.055 (2) | 0.035 (2) | 0.048 (3) | −0.0061 (17) | 0.003 (2) | 0.002 (2) |
C14 | 0.045 (2) | 0.0367 (19) | 0.044 (2) | −0.0017 (16) | 0.000 (2) | −0.001 (2) |
C15 | 0.0429 (18) | 0.0327 (17) | 0.037 (2) | 0.0001 (15) | −0.0041 (17) | −0.0011 (19) |
Geometric parameters (Å, º) top
O1—C7 | 1.218 (7) | C4—H4 | 0.9300 |
O2—C9 | 1.220 (5) | C5—C6 | 1.398 (4) |
N1—C7 | 1.342 (5) | C5—H5 | 0.9300 |
N1—N2 | 1.376 (5) | C6—H6 | 0.9300 |
N1—H1n | 0.8600 | C8—C15 | 1.458 (5) |
N2—C8 | 1.286 (5) | C8—C9 | 1.521 (6) |
N3—C9 | 1.351 (5) | C10—C11 | 1.387 (5) |
N3—C10 | 1.398 (5) | C10—C15 | 1.395 (6) |
N3—H3n | 0.8600 | C11—C12 | 1.385 (7) |
C1—C2 | 1.391 (4) | C11—H11 | 0.9300 |
C1—C6 | 1.398 (4) | C12—C13 | 1.381 (7) |
C1—C7 | 1.502 (5) | C12—H12 | 0.9300 |
C2—C3 | 1.396 (4) | C13—C14 | 1.396 (5) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.382 (4) | C14—C15 | 1.376 (6) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.372 (4) | | |
| | | |
C7—N1—N2 | 119.9 (4) | O1—C7—C1 | 121.5 (4) |
C7—N1—H1n | 120.0 | N1—C7—C1 | 115.3 (4) |
N2—N1—H1n | 120.0 | N2—C8—C15 | 126.3 (4) |
C8—N2—N1 | 114.9 (4) | N2—C8—C9 | 127.7 (3) |
C9—N3—C10 | 111.6 (3) | C15—C8—C9 | 106.0 (3) |
C9—N3—H3n | 124.2 | O2—C9—N3 | 128.2 (4) |
C10—N3—H3n | 124.2 | O2—C9—C8 | 126.1 (4) |
C2—C1—C6 | 120.3 (3) | N3—C9—C8 | 105.7 (3) |
C2—C1—C7 | 116.4 (3) | C11—C10—C15 | 120.9 (4) |
C6—C1—C7 | 123.3 (3) | C11—C10—N3 | 128.8 (4) |
C1—C2—C3 | 119.2 (4) | C15—C10—N3 | 110.3 (3) |
C1—C2—H2 | 120.4 | C12—C11—C10 | 117.3 (4) |
C3—C2—H2 | 120.4 | C12—C11—H11 | 121.4 |
C4—C3—C2 | 120.7 (4) | C10—C11—H11 | 121.4 |
C4—C3—H3 | 119.7 | C13—C12—C11 | 122.2 (4) |
C2—C3—H3 | 119.7 | C13—C12—H12 | 118.9 |
C5—C4—C3 | 119.9 (3) | C11—C12—H12 | 118.9 |
C5—C4—H4 | 120.0 | C12—C13—C14 | 120.2 (4) |
C3—C4—H4 | 120.0 | C12—C13—H13 | 119.9 |
C4—C5—C6 | 120.8 (4) | C14—C13—H13 | 119.9 |
C4—C5—H5 | 119.6 | C15—C14—C13 | 118.1 (4) |
C6—C5—H5 | 119.6 | C15—C14—H14 | 121.0 |
C5—C6—C1 | 119.1 (4) | C13—C14—H14 | 121.0 |
C5—C6—H6 | 120.5 | C14—C15—C10 | 121.3 (3) |
C1—C6—H6 | 120.5 | C14—C15—C8 | 132.4 (4) |
O1—C7—N1 | 123.3 (4) | C10—C15—C8 | 106.3 (3) |
| | | |
C7—N1—N2—C8 | 175.8 (4) | C15—C8—C9—O2 | 179.3 (4) |
C6—C1—C2—C3 | 1.8 (8) | N2—C8—C9—N3 | −179.9 (4) |
C7—C1—C2—C3 | −178.0 (5) | C15—C8—C9—N3 | −0.3 (4) |
C1—C2—C3—C4 | −1.7 (9) | C9—N3—C10—C11 | 179.4 (4) |
C2—C3—C4—C5 | 1.3 (9) | C9—N3—C10—C15 | 0.4 (5) |
C3—C4—C5—C6 | −1.0 (9) | C15—C10—C11—C12 | 1.4 (6) |
C4—C5—C6—C1 | 1.2 (8) | N3—C10—C11—C12 | −177.6 (4) |
C2—C1—C6—C5 | −1.6 (7) | C10—C11—C12—C13 | −1.4 (7) |
C7—C1—C6—C5 | 178.3 (5) | C11—C12—C13—C14 | −0.2 (7) |
N2—N1—C7—O1 | −1.4 (7) | C12—C13—C14—C15 | 1.8 (6) |
N2—N1—C7—C1 | 178.7 (3) | C13—C14—C15—C10 | −1.8 (6) |
C2—C1—C7—O1 | 8.0 (7) | C13—C14—C15—C8 | 178.1 (4) |
C6—C1—C7—O1 | −171.9 (4) | C11—C10—C15—C14 | 0.2 (6) |
C2—C1—C7—N1 | −172.1 (4) | N3—C10—C15—C14 | 179.3 (4) |
C6—C1—C7—N1 | 8.0 (6) | C11—C10—C15—C8 | −179.7 (4) |
N1—N2—C8—C15 | −179.8 (4) | N3—C10—C15—C8 | −0.6 (4) |
N1—N2—C8—C9 | −0.3 (6) | N2—C8—C15—C14 | 0.2 (8) |
C10—N3—C9—O2 | −179.7 (4) | C9—C8—C15—C14 | −179.4 (4) |
C10—N3—C9—C8 | −0.1 (5) | N2—C8—C15—C10 | −179.9 (4) |
N2—C8—C9—O2 | −0.3 (7) | C9—C8—C15—C10 | 0.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2 | 0.86 | 2.01 | 2.699 (5) | 137 |
N3—H3n···O1i | 0.86 | 2.12 | 2.862 (5) | 145 |
Symmetry code: (i) x−1/2, −y+3/2, z+1. |
Experimental details
Crystal data |
Chemical formula | C15H11N3O2 |
Mr | 265.27 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 295 |
a, b, c (Å) | 8.0023 (9), 28.549 (3), 5.2574 (6) |
V (Å3) | 1201.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.34 × 0.21 × 0.15 |
|
Data collection |
Diffractometer | Bruker SMART area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6999, 1463, 1176 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.641 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.191, 1.08 |
No. of reflections | 1463 |
No. of parameters | 181 |
No. of restraints | 10 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.29 |
Absolute structure | Flack parameter not calculated. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2 | 0.86 | 2.01 | 2.699 (5) | 137 |
N3—H3n···O1i | 0.86 | 2.12 | 2.862 (5) | 145 |
Symmetry code: (i) x−1/2, −y+3/2, z+1. |
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The preceeding report describes the structure of the monoclinic form of isatin 3-benzoylhydrazone (Ali et al., 2005). In the orthorhombic form, the chain formed by hydrogen-bonded molecules propages by twofold screw axial translations (Fig. 1), whereas in the monoclinic form the chain formed by hydrogen bonded molecules propagates by glide planes. The orthorhombic form is significantly denser (density = 1.467 Mg m−3) than the monoclinic form (density = 1.392 Mg m−3), as the polymeric chain is more flexible owing to a more adaptable, helical construction.