Literature DB >> 21579996

3,4,5-Trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide-1H-indole-2-carbaldehyde azine-methanol (2/1/2).

Hamid Khaledi, Abeer A Alhadi, Hapipah Mohd Ali, Ward T Robinson, Mahmood A Abdulla.   

Abstract

The title compound, 2C(16)H(13)N(3)O(4)·C(18)H(14)N(4)·2CH(4)O, was crystallized from the reaction between 3,4,5-trihydroxy-benzoyl-hydrazine and indole-2-carbaldehyde in a mixture of ethanol and methanol. The compound is a stoichiometric 2:1 cocrystal of the methanol-solvated reaction product, 3,4,5-trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide and 1H-indole-2-carbaldehyde azine that arose unexpectedly during the synthesis. The former mol-ecules are linked by O-H⋯O hydrogen bonds and also by π-π stacking inter-actions between benzoyl-hydrazide rings into a two-dimensional network. The methanol solvent mol-ecules are hydrogen bonded to this network. The centrosymmetric azine mol-ecules are not engaged in hydrogen bonding.

Entities:  

Year:  2009        PMID： 21579996      PMCID： PMC2980105          DOI： 10.1107/S1600536809052465

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the crystal structures of some compounds similar to 3,4,5-trihydr­oxy-N′-[(1H-indol-2-yl)methyl­idene]benzoyl­hydrazide, see: Khaledi et al. (2008a ▶,b ▶, 2009a ▶,b ▶). For the structure of 1H-indole-2-carbaldehyde azine, see: Rizal et al. (2008 ▶). For the biological activity of gallic acid (3,4,5-trihydroxybenzoic acid) derivatives see: Arunkumar et al. (2006 ▶); Saxena et al. (2008 ▶).

Experimental

Crystal data

2C16H13N3O4·C18H14N4·2CH4O M = 973.00 Triclinic, a = 7.4642 (15) Å b = 12.791 (2) Å c = 25.079 (5) Å α = 95.918 (3)° β = 95.166 (4)° γ = 101.451 (4)° V = 2319.3 (8) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 100 K 0.50 × 0.12 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.997 10985 measured reflections 7939 independent reflections 4029 reflections with I > 2σ(I) R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.064 wR(F 2) = 0.153 S = 0.98 7939 reflections 693 parameters 14 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.30 e Å−3 Δρmin = −0.32 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052465/om2302sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052465/om2302Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
2C16H13N3O4·C18H14N4·2CH4OZ = 2
Mr = 973.00F(000) = 1020
Triclinic, P1Dx = 1.393 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4642 (15) ÅCell parameters from 754 reflections
b = 12.791 (2) Åθ = 2.5–20.7°
c = 25.079 (5) ŵ = 0.10 mm−1
α = 95.918 (3)°T = 100 K
β = 95.166 (4)°Lath, yellow
γ = 101.451 (4)°0.50 × 0.12 × 0.03 mm
V = 2319.3 (8) Å3
Bruker APEXII CCD diffractometer7939 independent reflections
Radiation source: fine-focus sealed tube4029 reflections with I > 2σ(I)
graphiteRint = 0.054
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→8
Tmin = 0.952, Tmax = 0.997k = −15→13
10985 measured reflectionsl = −29→29
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3
7939 reflections(Δ/σ)max = 0.021
693 parametersΔρmax = 0.30 e Å−3
14 restraintsΔρmin = −0.31 e Å−3
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.
xyzUiso*/Ueq
O100.7343 (4)0.2306 (2)0.60742 (10)0.0276 (7)
O130.7280 (4)0.0510 (2)0.41802 (11)0.0333 (8)
H13O0.749 (6)0.003 (3)0.3953 (14)0.050*
O140.7874 (4)−0.1457 (2)0.42855 (11)0.0280 (7)
H14O0.823 (6)−0.201 (2)0.4370 (17)0.042*
O150.8285 (4)−0.2137 (2)0.52914 (10)0.0259 (7)
H15O0.846 (6)−0.225 (3)0.5616 (6)0.039*
N10.5730 (5)0.2917 (3)0.78752 (12)0.0211 (8)
H1N0.571 (5)0.321 (3)0.7570 (8)0.025*
N20.6671 (5)0.1652 (2)0.70038 (13)0.0242 (8)
N30.6927 (5)0.0943 (3)0.65781 (13)0.0260 (8)
H3N0.668 (5)0.0250 (10)0.6599 (15)0.031*
C10.6341 (5)0.1973 (3)0.79275 (15)0.0203 (9)
C20.6431 (5)0.1802 (3)0.84590 (15)0.0263 (10)
H20.68150.12150.86040.032*
C30.5848 (5)0.2656 (3)0.87524 (15)0.0232 (10)
C40.5625 (6)0.2922 (3)0.92965 (16)0.0290 (11)
H40.59370.24860.95600.035*
C50.4951 (6)0.3823 (3)0.94423 (16)0.0317 (11)
H50.47910.40070.98090.038*
C60.4495 (6)0.4473 (3)0.90547 (17)0.0325 (11)
H60.40250.50880.91670.039*
C70.4705 (5)0.4250 (3)0.85215 (16)0.0263 (10)
H70.43860.46960.82630.032*
C80.5402 (5)0.3347 (3)0.83727 (15)0.0222 (10)
C90.6730 (5)0.1316 (3)0.74681 (16)0.0258 (10)
H90.70280.06390.75090.031*
C100.7225 (6)0.1329 (3)0.61037 (16)0.0235 (10)
C110.7412 (5)0.0573 (3)0.56412 (15)0.0199 (9)
C120.7246 (5)0.0893 (3)0.51285 (15)0.0219 (10)
H120.70200.15850.50830.026*
C130.7412 (5)0.0194 (3)0.46881 (15)0.0207 (9)
C140.7731 (5)−0.0820 (3)0.47460 (15)0.0203 (9)
C150.7928 (5)−0.1131 (3)0.52580 (15)0.0191 (9)
C160.7771 (5)−0.0445 (3)0.57041 (15)0.0223 (10)
H160.7907−0.06610.60540.027*
O260.8842 (4)0.7516 (2)0.62971 (10)0.0246 (7)
O291.3673 (4)0.6412 (2)0.51863 (11)0.0276 (7)
H29O1.430 (5)0.601 (3)0.5035 (15)0.041*
O301.3089 (4)0.4224 (2)0.51396 (10)0.0225 (7)
H30O1.254 (5)0.3578 (13)0.5053 (15)0.034*
O311.0303 (4)0.3140 (2)0.56466 (11)0.0279 (7)
H31O0.938 (4)0.293 (3)0.5802 (15)0.042*
N40.5999 (5)0.7939 (3)0.79555 (12)0.0230 (8)
H4N0.609 (5)0.820 (3)0.7648 (8)0.028*
N50.7553 (5)0.6765 (2)0.71588 (12)0.0243 (8)
N60.8261 (5)0.6142 (3)0.67896 (13)0.0240 (8)
H6N0.818 (5)0.5464 (12)0.6837 (15)0.029*
C170.6739 (5)0.7044 (3)0.80452 (15)0.0233 (10)
C180.6735 (5)0.6888 (3)0.85733 (15)0.0241 (10)
H180.71630.63310.87360.029*
C190.5975 (5)0.7705 (3)0.88380 (15)0.0232 (10)
C200.5626 (6)0.7976 (3)0.93695 (16)0.0284 (11)
H200.59550.75760.96480.034*
C210.4798 (6)0.8830 (3)0.94795 (16)0.0312 (11)
H210.45620.90240.98380.037*
C220.4298 (6)0.9418 (3)0.90718 (17)0.0315 (11)
H220.37100.99960.91600.038*
C230.4630 (5)0.9184 (3)0.85492 (16)0.0250 (10)
H230.42640.95830.82740.030*
C240.5516 (5)0.8349 (3)0.84352 (15)0.0209 (9)
C250.7390 (5)0.6424 (3)0.76214 (15)0.0233 (10)
H250.77010.57580.76830.028*
C260.8945 (5)0.6580 (3)0.63666 (15)0.0209 (9)
C270.9906 (5)0.5921 (3)0.60161 (14)0.0201 (9)
C281.1271 (5)0.6445 (3)0.57419 (14)0.0198 (9)
H281.14940.72060.57560.024*
C291.2315 (5)0.5871 (3)0.54470 (15)0.0209 (9)
C301.1997 (5)0.4760 (3)0.54255 (14)0.0183 (9)
C311.0592 (5)0.4240 (3)0.56948 (14)0.0185 (9)
C320.9561 (5)0.4800 (3)0.59929 (14)0.0188 (9)
H320.86270.44340.61810.023*
N7−0.1199 (5)0.3424 (3)1.11800 (14)0.0329 (9)
H7N−0.160 (5)0.2730 (11)1.1082 (15)0.039*
N8−0.0309 (5)0.2620 (3)1.01631 (15)0.0412 (10)
N90.0213 (5)0.2391 (3)0.96486 (15)0.0413 (10)
N100.0984 (5)0.1700 (3)0.86232 (16)0.0390 (10)
H10N0.140 (6)0.2386 (12)0.8734 (17)0.047*
C33−0.0304 (6)0.4065 (4)1.08362 (17)0.0338 (11)
C340.0234 (6)0.5092 (4)1.10970 (17)0.0338 (11)
H340.08830.56941.09520.041*
C35−0.0343 (6)0.5100 (4)1.16199 (17)0.0318 (11)
C36−0.0175 (6)0.5877 (4)1.20641 (18)0.0365 (12)
H360.04270.65981.20470.044*
C37−0.0892 (6)0.5589 (4)1.25316 (18)0.0364 (12)
H37−0.07830.61161.28350.044*
C38−0.1782 (6)0.4520 (4)1.25592 (18)0.0355 (12)
H38−0.22670.43371.28830.043*
C39−0.1965 (6)0.3734 (4)1.21283 (17)0.0342 (11)
H39−0.25650.30141.21510.041*
C40−0.1247 (6)0.4023 (3)1.16585 (17)0.0299 (11)
C410.0086 (6)0.3637 (4)1.03193 (17)0.0351 (12)
H410.06480.41131.00870.042*
C42−0.0074 (6)0.1373 (4)0.94922 (19)0.0404 (12)
H42−0.05280.08740.97290.048*
C430.0283 (6)0.0996 (4)0.8971 (2)0.0404 (12)
C44−0.0064 (6)−0.0023 (4)0.8699 (2)0.0450 (13)
H44−0.0547−0.06670.88420.054*
C450.0423 (6)0.0051 (4)0.8166 (2)0.0388 (12)
C460.0367 (6)−0.0702 (4)0.7703 (2)0.0505 (15)
H46−0.0038−0.14500.77160.061*
C470.0905 (7)−0.0332 (5)0.7238 (2)0.0575 (16)
H470.0874−0.08310.69270.069*
C480.1500 (6)0.0768 (4)0.7210 (2)0.0519 (15)
H480.18420.10020.68790.062*
C490.1598 (6)0.1511 (4)0.76502 (19)0.0454 (13)
H490.20180.22560.76310.055*
C500.1067 (6)0.1146 (4)0.81268 (19)0.0379 (12)
O510.3727 (4)0.6124 (2)0.31454 (11)0.0291 (7)
H51O0.348 (6)0.6718 (18)0.3249 (16)0.044*
C510.5272 (6)0.6038 (4)0.35040 (18)0.0448 (13)
H51A0.63260.66070.34640.067*
H51B0.55800.53350.34180.067*
H51C0.49710.61140.38760.067*
O520.3718 (4)0.1291 (2)0.31264 (11)0.0270 (7)
H52O0.303 (5)0.173 (3)0.3177 (17)0.040*
C520.5328 (6)0.1969 (3)0.34338 (17)0.0348 (11)
H52A0.55200.26850.33150.052*
H52B0.64040.16560.33780.052*
H52C0.51570.20280.38180.052*
U11U22U33U12U13U23
O100.0363 (18)0.0170 (17)0.0324 (17)0.0056 (13)0.0150 (14)0.0060 (13)
O130.052 (2)0.034 (2)0.0181 (17)0.0156 (16)0.0047 (15)0.0088 (13)
O140.0370 (19)0.0241 (18)0.0239 (16)0.0105 (14)0.0041 (14)−0.0008 (13)
O150.0401 (19)0.0190 (16)0.0207 (16)0.0095 (14)0.0071 (15)0.0033 (13)
N10.025 (2)0.023 (2)0.0172 (19)0.0072 (16)0.0037 (16)0.0043 (15)
N20.034 (2)0.0181 (19)0.021 (2)0.0060 (16)0.0088 (16)0.0013 (15)
N30.036 (2)0.0176 (19)0.024 (2)0.0029 (17)0.0120 (17)−0.0006 (16)
C10.019 (2)0.019 (2)0.025 (2)0.0060 (18)0.0048 (18)0.0023 (18)
C20.029 (3)0.024 (3)0.024 (2)0.003 (2)0.001 (2)0.0049 (19)
C30.028 (3)0.019 (2)0.021 (2)0.0014 (19)0.0034 (19)0.0030 (18)
C40.036 (3)0.031 (3)0.018 (2)0.004 (2)0.003 (2)0.0018 (19)
C50.041 (3)0.033 (3)0.019 (2)0.004 (2)0.005 (2)−0.003 (2)
C60.032 (3)0.033 (3)0.031 (3)0.004 (2)0.008 (2)−0.005 (2)
C70.025 (3)0.025 (3)0.029 (3)0.007 (2)0.003 (2)0.0004 (19)
C80.022 (2)0.024 (2)0.019 (2)0.0013 (19)0.0024 (18)0.0006 (18)
C90.026 (3)0.024 (3)0.026 (2)0.0009 (19)0.004 (2)0.0033 (19)
C100.025 (2)0.017 (2)0.027 (2)−0.0002 (19)0.0068 (19)0.0010 (18)
C110.019 (2)0.018 (2)0.023 (2)0.0029 (18)0.0064 (18)0.0027 (18)
C120.026 (2)0.015 (2)0.025 (2)0.0039 (18)0.0035 (19)0.0062 (18)
C130.021 (2)0.025 (2)0.017 (2)0.0053 (19)0.0022 (18)0.0061 (18)
C140.020 (2)0.022 (2)0.016 (2)0.0013 (18)0.0054 (18)−0.0020 (18)
C150.021 (2)0.012 (2)0.025 (2)0.0049 (17)0.0039 (18)0.0047 (17)
C160.026 (2)0.019 (2)0.022 (2)0.0021 (19)0.0061 (19)0.0043 (18)
O260.0384 (18)0.0154 (16)0.0228 (15)0.0097 (13)0.0091 (13)0.0030 (12)
O290.0279 (18)0.0197 (17)0.0383 (18)0.0050 (13)0.0181 (14)0.0051 (13)
O300.0223 (17)0.0174 (16)0.0282 (16)0.0030 (13)0.0085 (13)0.0017 (13)
O310.0291 (18)0.0205 (17)0.0366 (18)0.0061 (14)0.0190 (14)0.0000 (13)
N40.026 (2)0.025 (2)0.019 (2)0.0074 (16)0.0045 (17)0.0001 (16)
N50.032 (2)0.025 (2)0.0176 (19)0.0059 (16)0.0091 (16)0.0011 (15)
N60.035 (2)0.019 (2)0.0201 (19)0.0070 (17)0.0120 (16)0.0019 (16)
C170.021 (2)0.026 (3)0.024 (2)0.0051 (19)0.0069 (19)0.0025 (19)
C180.028 (3)0.027 (2)0.021 (2)0.011 (2)0.0047 (19)0.0057 (18)
C190.026 (2)0.022 (2)0.022 (2)0.0047 (19)0.0036 (19)0.0035 (18)
C200.034 (3)0.029 (3)0.021 (2)0.004 (2)0.004 (2)0.0020 (19)
C210.041 (3)0.031 (3)0.020 (2)0.005 (2)0.010 (2)−0.004 (2)
C220.032 (3)0.027 (3)0.038 (3)0.011 (2)0.010 (2)0.001 (2)
C230.030 (3)0.020 (2)0.028 (2)0.010 (2)0.008 (2)0.0051 (19)
C240.021 (2)0.022 (2)0.017 (2)0.0028 (19)0.0016 (18)−0.0025 (18)
C250.024 (2)0.023 (2)0.025 (2)0.0063 (19)0.0065 (19)0.0055 (19)
C260.022 (2)0.018 (2)0.021 (2)0.0015 (18)0.0012 (18)0.0011 (18)
C270.020 (2)0.025 (2)0.014 (2)0.0049 (19)0.0011 (17)−0.0009 (17)
C280.030 (2)0.010 (2)0.020 (2)0.0056 (18)0.0037 (19)0.0026 (17)
C290.019 (2)0.019 (2)0.024 (2)0.0018 (18)0.0028 (19)0.0010 (18)
C300.014 (2)0.022 (2)0.018 (2)0.0046 (18)0.0054 (17)−0.0017 (17)
C310.021 (2)0.012 (2)0.021 (2)0.0011 (18)0.0031 (18)0.0022 (17)
C320.022 (2)0.018 (2)0.017 (2)0.0022 (18)0.0083 (18)0.0044 (17)
N70.030 (2)0.029 (2)0.037 (2)−0.0003 (19)0.0046 (18)0.0002 (19)
N80.036 (2)0.050 (3)0.035 (2)0.005 (2)0.0053 (19)−0.001 (2)
N90.033 (2)0.052 (3)0.039 (2)0.009 (2)0.0062 (19)0.003 (2)
N100.029 (2)0.037 (3)0.047 (3)0.003 (2)0.0061 (19)−0.011 (2)
C330.023 (3)0.046 (3)0.032 (3)0.005 (2)0.003 (2)0.006 (2)
C340.026 (3)0.035 (3)0.042 (3)0.006 (2)−0.001 (2)0.011 (2)
C350.021 (3)0.038 (3)0.037 (3)0.008 (2)−0.002 (2)0.010 (2)
C360.030 (3)0.028 (3)0.048 (3)0.000 (2)−0.004 (2)0.004 (2)
C370.033 (3)0.039 (3)0.035 (3)0.008 (2)−0.003 (2)−0.001 (2)
C380.023 (3)0.044 (3)0.037 (3)0.002 (2)0.000 (2)0.009 (2)
C390.024 (3)0.032 (3)0.042 (3)−0.001 (2)−0.003 (2)0.005 (2)
C400.019 (2)0.034 (3)0.034 (3)0.003 (2)−0.002 (2)0.001 (2)
C410.019 (3)0.054 (3)0.034 (3)0.010 (2)0.003 (2)0.009 (2)
C420.030 (3)0.047 (3)0.045 (3)0.009 (2)−0.001 (2)0.010 (3)
C430.031 (3)0.038 (3)0.052 (3)0.008 (2)0.004 (3)0.003 (3)
C440.029 (3)0.031 (3)0.072 (4)0.006 (2)0.000 (3)0.003 (3)
C450.022 (3)0.035 (3)0.056 (3)0.007 (2)−0.002 (2)−0.006 (2)
C460.030 (3)0.039 (3)0.075 (4)0.008 (2)−0.008 (3)−0.019 (3)
C470.037 (3)0.063 (4)0.064 (4)0.009 (3)0.007 (3)−0.032 (3)
C480.038 (3)0.053 (4)0.057 (4)−0.002 (3)0.018 (3)−0.020 (3)
C490.033 (3)0.047 (3)0.050 (3)0.001 (2)0.009 (3)−0.012 (3)
C500.022 (3)0.035 (3)0.051 (3)0.005 (2)0.003 (2)−0.016 (2)
O510.0360 (19)0.0255 (18)0.0272 (17)0.0103 (15)0.0070 (14)−0.0004 (13)
C510.040 (3)0.053 (3)0.042 (3)0.013 (3)−0.004 (2)0.005 (2)
O520.0322 (19)0.0208 (18)0.0285 (17)0.0073 (13)0.0044 (14)0.0019 (13)
C520.027 (3)0.040 (3)0.034 (3)0.002 (2)−0.003 (2)0.007 (2)
O10—C101.246 (4)C22—H220.9500
O13—C131.376 (4)C23—C241.383 (5)
O13—H13O0.844 (10)C23—H230.9500
O14—C141.368 (4)C25—H250.9500
O14—H14O0.843 (10)C26—C271.482 (5)
O15—C151.374 (4)C27—C281.382 (5)
O15—H15O0.845 (10)C27—C321.400 (5)
N1—C81.373 (5)C28—C291.383 (5)
N1—C11.387 (5)C28—H280.9500
N1—H1N0.884 (10)C29—C301.388 (5)
N2—C91.282 (5)C30—C311.393 (5)
N2—N31.380 (4)C31—C321.370 (5)
N3—C101.354 (5)C32—H320.9500
N3—H3N0.877 (10)N7—C401.363 (5)
C1—C21.371 (5)N7—C331.376 (5)
C1—C91.440 (5)N7—H7N0.879 (10)
C2—C31.415 (5)N8—C411.286 (5)
C2—H20.9500N8—N91.400 (5)
C3—C41.405 (5)N9—C421.290 (5)
C3—C81.426 (5)N10—C431.378 (6)
C4—C51.375 (5)N10—C501.380 (5)
C4—H40.9500N10—H10N0.877 (10)
C5—C61.404 (6)C33—C341.371 (6)
C5—H50.9500C33—C411.432 (6)
C6—C71.368 (5)C34—C351.416 (6)
C6—H60.9500C34—H340.9500
C7—C81.389 (5)C35—C361.394 (6)
C7—H70.9500C35—C401.425 (6)
C9—H90.9500C36—C371.386 (6)
C10—C111.467 (5)C36—H360.9500
C11—C121.392 (5)C37—C381.409 (6)
C11—C161.401 (5)C37—H370.9500
C12—C131.378 (5)C38—C391.375 (6)
C12—H120.9500C38—H380.9500
C13—C141.384 (5)C39—C401.392 (6)
C14—C151.387 (5)C39—H390.9500
C15—C161.377 (5)C41—H410.9500
C16—H160.9500C42—C431.414 (6)
O26—C261.243 (4)C42—H420.9500
O29—C291.367 (4)C43—C441.371 (6)
O29—H29O0.845 (10)C44—C451.425 (6)
O30—C301.369 (4)C44—H440.9500
O30—H30O0.841 (10)C45—C501.405 (6)
O31—C311.372 (4)C45—C461.423 (6)
O31—H31O0.836 (10)C46—C471.367 (7)
N4—C241.370 (5)C46—H460.9500
N4—C171.396 (5)C47—C481.399 (7)
N4—H4N0.876 (10)C47—H470.9500
N5—C251.289 (5)C48—C491.367 (6)
N5—N61.369 (4)C48—H480.9500
N6—C261.344 (5)C49—C501.389 (6)
N6—H6N0.877 (10)C49—H490.9500
C17—C181.360 (5)O51—C511.427 (5)
C17—C251.438 (5)O51—H51O0.839 (10)
C18—C191.419 (5)C51—H51A0.9800
C18—H180.9500C51—H51B0.9800
C19—C201.403 (5)C51—H51C0.9800
C19—C241.428 (5)O52—C521.440 (5)
C20—C211.374 (5)O52—H52O0.837 (10)
C20—H200.9500C52—H52A0.9800
C21—C221.397 (6)C52—H52B0.9800
C21—H210.9500C52—H52C0.9800
C22—C231.369 (5)
C13—O13—H13O110 (3)O26—C26—C27122.7 (4)
C14—O14—H14O109 (3)N6—C26—C27116.9 (4)
C15—O15—H15O111 (3)C28—C27—C32120.0 (3)
C8—N1—C1109.0 (3)C28—C27—C26118.3 (4)
C8—N1—H1N128 (2)C32—C27—C26121.5 (3)
C1—N1—H1N123 (2)C27—C28—C29120.5 (4)
C9—N2—N3116.0 (3)C27—C28—H28119.7
C10—N3—N2117.8 (3)C29—C28—H28119.7
C10—N3—H3N121 (3)O29—C29—C28119.2 (3)
N2—N3—H3N120 (3)O29—C29—C30120.8 (3)
C2—C1—N1109.0 (3)C28—C29—C30120.0 (4)
C2—C1—C9129.2 (4)O30—C30—C29118.2 (3)
N1—C1—C9121.8 (4)O30—C30—C31122.9 (3)
C1—C2—C3107.8 (4)C29—C30—C31118.9 (3)
C1—C2—H2126.1C32—C31—O31121.9 (3)
C3—C2—H2126.1C32—C31—C30121.7 (4)
C4—C3—C2134.7 (4)O31—C31—C30116.4 (3)
C4—C3—C8118.5 (4)C31—C32—C27118.9 (3)
C2—C3—C8106.8 (3)C31—C32—H32120.5
C5—C4—C3119.1 (4)C27—C32—H32120.5
C5—C4—H4120.4C40—N7—C33109.8 (4)
C3—C4—H4120.4C40—N7—H7N130 (3)
C4—C5—C6120.7 (4)C33—N7—H7N120 (3)
C4—C5—H5119.6C41—N8—N9111.2 (4)
C6—C5—H5119.6C42—N9—N8112.7 (4)
C7—C6—C5122.2 (4)C43—N10—C50110.2 (4)
C7—C6—H6118.9C43—N10—H10N121 (3)
C5—C6—H6118.9C50—N10—H10N128 (3)
C6—C7—C8117.3 (4)C34—C33—N7108.4 (4)
C6—C7—H7121.3C34—C33—C41129.2 (4)
C8—C7—H7121.3N7—C33—C41122.2 (4)
N1—C8—C7130.5 (4)C33—C34—C35108.3 (4)
N1—C8—C3107.4 (3)C33—C34—H34125.9
C7—C8—C3122.1 (4)C35—C34—H34125.9
N2—C9—C1119.6 (4)C36—C35—C34135.0 (4)
N2—C9—H9120.2C36—C35—C40119.0 (4)
C1—C9—H9120.2C34—C35—C40106.0 (4)
O10—C10—N3119.5 (3)C37—C36—C35119.5 (4)
O10—C10—C11122.3 (4)C37—C36—H36120.3
N3—C10—C11118.2 (4)C35—C36—H36120.3
C12—C11—C16119.8 (3)C36—C37—C38120.4 (4)
C12—C11—C10118.2 (4)C36—C37—H37119.8
C16—C11—C10121.9 (4)C38—C37—H37119.8
C13—C12—C11119.2 (4)C39—C38—C37121.5 (4)
C13—C12—H12120.4C39—C38—H38119.3
C11—C12—H12120.4C37—C38—H38119.3
O13—C13—C12119.7 (3)C38—C39—C40118.1 (4)
O13—C13—C14119.0 (3)C38—C39—H39120.9
C12—C13—C14121.3 (4)C40—C39—H39120.9
O14—C14—C13117.1 (3)N7—C40—C39131.0 (4)
O14—C14—C15123.5 (4)N7—C40—C35107.5 (4)
C13—C14—C15119.4 (3)C39—C40—C35121.5 (4)
O15—C15—C16122.9 (4)N8—C41—C33121.3 (4)
O15—C15—C14116.8 (3)N8—C41—H41119.3
C16—C15—C14120.3 (4)C33—C41—H41119.3
C15—C16—C11119.9 (4)N9—C42—C43120.3 (5)
C15—C16—H16120.0N9—C42—H42119.8
C11—C16—H16120.0C43—C42—H42119.8
C29—O29—H29O113 (3)C44—C43—N10107.8 (4)
C30—O30—H30O109 (3)C44—C43—C42130.9 (5)
C31—O31—H31O107 (3)N10—C43—C42121.2 (4)
C24—N4—C17108.0 (3)C43—C44—C45108.2 (4)
C24—N4—H4N131 (3)C43—C44—H44125.9
C17—N4—H4N120 (3)C45—C44—H44125.9
C25—N5—N6116.1 (3)C50—C45—C46118.1 (5)
C26—N6—N5118.8 (3)C50—C45—C44107.0 (4)
C26—N6—H6N124 (3)C46—C45—C44134.9 (5)
N5—N6—H6N117 (3)C47—C46—C45119.0 (5)
C18—C17—N4109.7 (3)C47—C46—H46120.5
C18—C17—C25128.0 (4)C45—C46—H46120.5
N4—C17—C25122.2 (4)C46—C47—C48121.2 (5)
C17—C18—C19107.8 (4)C46—C47—H47119.4
C17—C18—H18126.1C48—C47—H47119.4
C19—C18—H18126.1C49—C48—C47121.3 (5)
C20—C19—C18134.9 (4)C49—C48—H48119.4
C20—C19—C24118.8 (4)C47—C48—H48119.4
C18—C19—C24106.3 (3)C48—C49—C50118.1 (5)
C21—C20—C19118.8 (4)C48—C49—H49121.0
C21—C20—H20120.6C50—C49—H49121.0
C19—C20—H20120.6N10—C50—C49130.9 (4)
C20—C21—C22121.0 (4)N10—C50—C45106.9 (4)
C20—C21—H21119.5C49—C50—C45122.2 (4)
C22—C21—H21119.5C51—O51—H51O106 (3)
C23—C22—C21122.0 (4)O51—C51—H51A109.5
C23—C22—H22119.0O51—C51—H51B109.5
C21—C22—H22119.0H51A—C51—H51B109.5
C22—C23—C24117.7 (4)O51—C51—H51C109.5
C22—C23—H23121.2H51A—C51—H51C109.5
C24—C23—H23121.2H51B—C51—H51C109.5
N4—C24—C23130.2 (4)C52—O52—H52O95 (3)
N4—C24—C19108.1 (3)O52—C52—H52A109.5
C23—C24—C19121.6 (4)O52—C52—H52B109.5
N5—C25—C17120.5 (4)H52A—C52—H52B109.5
N5—C25—H25119.8O52—C52—H52C109.5
C17—C25—H25119.8H52A—C52—H52C109.5
O26—C26—N6120.4 (3)H52B—C52—H52C109.5
D—H···AD—HH···AD···AD—H···A
O13—H13O···O140.84 (1)2.21 (4)2.674 (4)115 (4)
O14—H14O···O31i0.84 (1)1.98 (2)2.778 (4)158 (4)
O14—H14O···O150.84 (1)2.33 (4)2.763 (4)112 (3)
O15—H15O···O26ii0.85 (1)1.77 (1)2.617 (4)179 (4)
N1—H1N···O51iii0.88 (1)2.11 (1)2.976 (4)167 (3)
N3—H3N···O52iv0.88 (1)2.13 (2)2.983 (4)165 (4)
O29—H29O···O30v0.85 (1)2.11 (2)2.858 (4)148 (4)
O30—H30O···O15i0.84 (1)1.91 (2)2.732 (4)165 (4)
O31—H31O···O100.84 (1)1.80 (1)2.626 (4)172 (4)
N4—H4N···O52iii0.88 (1)2.12 (1)2.992 (4)175 (3)
N6—H6N···O51iii0.88 (1)2.24 (2)3.011 (4)146 (3)
O51—H51O···O10iii0.84 (1)2.21 (3)2.934 (4)145 (4)
O51—H51O···N2iii0.84 (1)2.26 (3)2.975 (4)143 (4)
O52—H52O···N5iii0.84 (1)2.29 (3)2.963 (4)138 (4)
O52—H52O···O26iii0.84 (1)2.29 (2)3.046 (4)150 (4)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O13—H13O⋯O140.84 (1)2.21 (4)2.674 (4)115 (4)
O14—H14O⋯O31i0.84 (1)1.98 (2)2.778 (4)158 (4)
O14—H14O⋯O150.84 (1)2.33 (4)2.763 (4)112 (3)
O15—H15O⋯O26ii0.85 (1)1.77 (1)2.617 (4)179 (4)
N1—H1N⋯O51iii0.88 (1)2.11 (1)2.976 (4)167 (3)
N3—H3N⋯O52iv0.88 (1)2.13 (2)2.983 (4)165 (4)
O29—H29O⋯O30v0.85 (1)2.11 (2)2.858 (4)148 (4)
O30—H30O⋯O15i0.84 (1)1.91 (2)2.732 (4)165 (4)
O31—H31O⋯O100.84 (1)1.80 (1)2.626 (4)172 (4)
N4—H4N⋯O52iii0.88 (1)2.12 (1)2.992 (4)175 (3)
N6—H6N⋯O51iii0.88 (1)2.24 (2)3.011 (4)146 (3)
O51—H51O⋯O10iii0.84 (1)2.21 (3)2.934 (4)145 (4)
O51—H51O⋯N2iii0.84 (1)2.26 (3)2.975 (4)143 (4)
O52—H52O⋯N5iii0.84 (1)2.29 (3)2.963 (4)138 (4)
O52—H52O⋯O26iii0.84 (1)2.29 (2)3.046 (4)150 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  3,4,5-Trihydr-oxy-N'-[(1-methyl-1H-indol-2-yl)methyl-idene]benzohydrazide.

Authors:  Hamid Khaledi; Siti Munirah Saharin; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-18

3.  N'-[(5-Chloro-1H-indol-3-yl)methyl-ene]-3,4,5-trihydroxy-benzohydrazide.

Authors:  Hamid Khaledi; Hapipah Mohd Ali; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-20

4.  N'-(5-Bromo-1H-indol-3-ylmethyl-idene)-3,4,5-trihydroxy-benzohydrazide.

Authors:  Hamid Khaledi; Hapipah Mohd Ali; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-11

5.  Gallic acid-based indanone derivatives as anticancer agents.

Authors:  Hari Om Saxena; Uzma Faridi; Suchita Srivastava; J K Kumar; M P Darokar; Suaib Luqman; C S Chanotiya; Vinay Krishna; Arvind S Negi; S P S Khanuja
Journal:  Bioorg Med Chem Lett       Date:  2008-06-14       Impact factor: 2.823

6.  1H-Indole-3-carbaldehyde azine.

Authors:  Mohd Razali Rizal; Hapipah M Ali; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-06

7.  3,4,5-Trihydr-oxy-N'-(1H-indol-3-yl-methyl-idene)benzohydrazide penta-hydrate.

Authors:  Hamid Khaledi; Hapipah Mohd Ali; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-29
  7 in total

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