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The two components of the title cocrystal, C10H10N3O·C18H18N3O3, are linked by a hydrazine–hydr­oxy N—H...O hydrogen bond; an inter­molecular amide–amide N—H...O inter­action that involves only the hydrazide component leads to the formation of a linear chain structure. Further inter­molecular O—H...O and N—H...O hydrogen bonds form a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010860/lh2323sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010860/lh2323Isup2.hkl
Contains datablock I

CCDC reference: 643054

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.147
  • Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H3N1 .. H4O .. 2.01 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.45 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27 PLAT414_ALERT_2_C Short Intra D-H..H-X H5N .. H22A .. 1.94 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3N1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
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 27.50 From the CIF: _reflns_number_total 2770 Count of symmetry unique reflns 2790 Completeness (_total/calc) 99.28% 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 8 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 6 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

1-(2,4-Dihydroxyphenyl)ethanone [(1H-indol-3-yl)acetyl]hydrazone– 2-(1H-indol-3-yl)acetohydrazide (1/1) top
Crystal data top
C10H10N3O·C18H18N3O3F(000) = 1080
Mr = 512.56Dx = 1.412 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 7984 reflections
a = 49.2086 (6) Åθ = 2.5–34.2°
b = 5.0292 (1) ŵ = 0.10 mm1
c = 9.8401 (1) ÅT = 173 K
β = 98.186 (1)°Block, yellow
V = 2410.41 (6) Å30.50 × 0.50 × 0.50 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
2726 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 0.8°
φ and ω scansh = 6361
16582 measured reflectionsk = 66
2770 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1185P)2 + 1.5332P]
where P = (Fo2 + 2Fc2)/3
2770 reflections(Δ/σ)max = 0.001
344 parametersΔρmax = 0.49 e Å3
2 restraintsΔρmin = 0.44 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49998 (5)0.5710 (5)0.7500 (3)0.0281 (5)
O20.29683 (5)0.2106 (4)0.1002 (2)0.0238 (5)
O30.36512 (5)0.0810 (4)0.3027 (2)0.0238 (5)
H3O0.35040.04370.25220.029*
O40.45568 (5)0.2371 (5)0.4311 (3)0.0287 (5)
H4o0.46230.39090.44110.034*
N10.58376 (6)0.5642 (5)1.0190 (3)0.0243 (5)
H1N0.59330.68531.06980.029*
N20.49390 (6)0.1523 (5)0.6672 (3)0.0250 (5)
H2N0.49860.01600.67830.030*
N30.47616 (6)0.2295 (6)0.5467 (3)0.0270 (6)
H3n0.46620.09230.51430.032*
H3n10.48600.28560.48450.032*
N40.25631 (6)0.4740 (5)0.2940 (3)0.0234 (5)
H4N0.26320.59880.34170.028*
N50.30807 (5)0.2086 (5)0.0457 (3)0.0201 (5)
H5n0.30350.35460.00150.024*
N60.33380 (5)0.1793 (5)0.1220 (3)0.0206 (5)
C10.59425 (7)0.3896 (6)0.9322 (3)0.0225 (6)
C20.62102 (7)0.3586 (7)0.9048 (3)0.0266 (6)
H20.63540.47100.94550.032*
C30.62568 (7)0.1558 (7)0.8153 (4)0.0287 (7)
H30.64370.12870.79380.034*
C40.60430 (8)0.0102 (7)0.7558 (3)0.0289 (7)
H40.60820.14880.69600.035*
C50.57759 (7)0.0233 (6)0.7823 (3)0.0239 (6)
H50.56320.08920.74090.029*
C60.57232 (6)0.2280 (6)0.8719 (3)0.0202 (6)
C70.54807 (6)0.3167 (6)0.9259 (3)0.0214 (6)
C80.55625 (7)0.5205 (6)1.0141 (3)0.0231 (6)
H80.54450.61761.06470.028*
C90.51969 (7)0.2063 (6)0.8930 (3)0.0240 (6)
H9A0.50960.23820.97170.029*
H9B0.52080.01160.88000.029*
C100.50367 (6)0.3291 (6)0.7645 (3)0.0221 (6)
C110.22908 (7)0.4071 (6)0.3044 (3)0.0215 (6)
C120.20624 (7)0.5057 (6)0.3907 (3)0.0262 (6)
H120.20800.64430.45450.031*
C130.18113 (7)0.3932 (7)0.3795 (4)0.0290 (7)
H130.16520.45830.43580.035*
C140.17834 (7)0.1840 (7)0.2866 (4)0.0272 (7)
H140.16070.11010.28240.033*
C150.20086 (6)0.0855 (6)0.2019 (3)0.0237 (6)
H150.19890.05520.13960.028*
C160.22670 (6)0.1981 (6)0.2100 (3)0.0199 (6)
C170.25395 (6)0.1454 (6)0.1408 (3)0.0207 (6)
C180.27114 (7)0.3144 (6)0.1969 (3)0.0220 (6)
H180.29050.32050.17230.026*
C190.26151 (6)0.0561 (6)0.0286 (3)0.0205 (6)
H19A0.26070.23680.06890.025*
H19B0.24810.04740.03740.025*
C200.29013 (6)0.0049 (6)0.0463 (3)0.0195 (6)
C210.35351 (6)0.3331 (5)0.0933 (3)0.0183 (5)
C220.35021 (6)0.5367 (6)0.0187 (3)0.0218 (6)
H22A0.33400.49390.08510.033*
H22B0.34790.71280.02070.033*
H22C0.36660.53670.06510.033*
C230.38022 (6)0.2960 (6)0.1788 (3)0.0183 (5)
C240.38470 (6)0.0927 (6)0.2794 (3)0.0200 (6)
C250.41000 (7)0.0682 (6)0.3625 (3)0.0227 (6)
H250.41290.07040.42860.027*
C260.43099 (6)0.2475 (6)0.3484 (4)0.0230 (6)
C270.42697 (6)0.4506 (6)0.2506 (3)0.0227 (6)
H270.44130.57290.24130.027*
C280.40207 (6)0.4719 (6)0.1679 (3)0.0211 (6)
H280.39950.60970.10120.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0298 (12)0.0107 (10)0.0417 (13)0.0001 (8)0.0028 (9)0.0000 (9)
O20.0214 (10)0.0105 (9)0.0392 (12)0.0005 (8)0.0030 (8)0.0044 (8)
O30.0222 (10)0.0123 (10)0.0367 (12)0.0024 (8)0.0035 (8)0.0027 (8)
O40.0224 (11)0.0150 (11)0.0462 (14)0.0008 (9)0.0032 (9)0.0003 (10)
N10.0261 (13)0.0142 (12)0.0316 (13)0.0008 (10)0.0002 (10)0.0035 (10)
N20.0266 (13)0.0117 (11)0.0353 (14)0.0021 (10)0.0001 (10)0.0002 (10)
N30.0287 (14)0.0159 (12)0.0343 (14)0.0015 (10)0.0031 (11)0.0006 (10)
N40.0265 (13)0.0136 (11)0.0304 (13)0.0023 (10)0.0048 (10)0.0014 (10)
N50.0196 (12)0.0117 (11)0.0287 (12)0.0007 (9)0.0023 (9)0.0023 (9)
N60.0177 (11)0.0131 (11)0.0305 (13)0.0010 (9)0.0018 (9)0.0004 (10)
C10.0271 (15)0.0128 (13)0.0265 (14)0.0005 (11)0.0003 (11)0.0006 (11)
C20.0264 (16)0.0192 (15)0.0336 (16)0.0018 (12)0.0022 (12)0.0044 (12)
C30.0305 (16)0.0234 (16)0.0331 (17)0.0075 (13)0.0073 (12)0.0066 (13)
C40.0425 (19)0.0180 (14)0.0267 (15)0.0099 (13)0.0066 (13)0.0008 (12)
C50.0326 (16)0.0135 (13)0.0243 (13)0.0020 (12)0.0004 (11)0.0015 (11)
C60.0240 (14)0.0121 (12)0.0238 (13)0.0012 (11)0.0009 (10)0.0019 (11)
C70.0240 (14)0.0121 (13)0.0276 (14)0.0010 (11)0.0017 (11)0.0012 (11)
C80.0267 (15)0.0165 (13)0.0258 (14)0.0008 (11)0.0023 (11)0.0000 (11)
C90.0231 (14)0.0150 (14)0.0334 (16)0.0013 (11)0.0021 (11)0.0028 (11)
C100.0180 (13)0.0133 (13)0.0350 (16)0.0003 (10)0.0041 (11)0.0023 (11)
C110.0253 (14)0.0122 (12)0.0273 (14)0.0015 (10)0.0049 (11)0.0031 (10)
C120.0308 (16)0.0157 (14)0.0321 (15)0.0037 (12)0.0049 (12)0.0007 (12)
C130.0258 (15)0.0254 (16)0.0348 (16)0.0056 (12)0.0011 (12)0.0021 (13)
C140.0217 (14)0.0212 (15)0.0388 (18)0.0003 (11)0.0050 (12)0.0041 (13)
C150.0202 (13)0.0180 (14)0.0335 (15)0.0002 (11)0.0059 (11)0.0003 (11)
C160.0228 (14)0.0100 (12)0.0270 (14)0.0027 (10)0.0036 (11)0.0033 (10)
C170.0187 (13)0.0114 (12)0.0322 (15)0.0009 (10)0.0040 (10)0.0033 (11)
C180.0241 (14)0.0154 (13)0.0269 (14)0.0021 (11)0.0046 (11)0.0028 (10)
C190.0178 (13)0.0124 (13)0.0312 (15)0.0002 (9)0.0029 (11)0.0006 (10)
C200.0191 (13)0.0116 (13)0.0279 (14)0.0016 (10)0.0039 (10)0.0017 (10)
C210.0214 (13)0.0072 (12)0.0272 (14)0.0003 (10)0.0061 (10)0.0019 (10)
C220.0232 (14)0.0127 (12)0.0301 (15)0.0005 (10)0.0059 (11)0.0014 (10)
C230.0199 (13)0.0088 (12)0.0266 (13)0.0006 (9)0.0045 (10)0.0010 (10)
C240.0203 (13)0.0112 (12)0.0293 (14)0.0020 (10)0.0066 (11)0.0008 (11)
C250.0247 (14)0.0116 (12)0.0317 (14)0.0021 (11)0.0037 (11)0.0002 (11)
C260.0214 (14)0.0119 (13)0.0356 (16)0.0019 (11)0.0037 (11)0.0028 (11)
C270.0192 (13)0.0129 (13)0.0365 (16)0.0023 (10)0.0059 (11)0.0002 (11)
C280.0219 (13)0.0122 (13)0.0299 (15)0.0011 (10)0.0057 (11)0.0021 (10)
Geometric parameters (Å, º) top
O1—C101.236 (4)C9—C101.522 (4)
O2—C201.231 (4)C9—H9A0.9900
O3—C241.344 (4)C9—H9B0.9900
O3—H3O0.8400C11—C121.400 (5)
O4—C261.364 (4)C11—C161.418 (4)
O4—H4O0.8400C12—C131.378 (5)
N1—C81.366 (4)C12—H120.9500
N1—C11.376 (4)C13—C141.413 (5)
N1—H1N0.8800C13—H130.9500
N2—C101.345 (4)C14—C151.380 (5)
N2—N31.422 (4)C14—H140.9500
N2—H2N0.8800C15—C161.404 (4)
N3—H3n0.8800C15—H150.9500
N3—H3n10.8800C16—C171.439 (4)
N4—C111.371 (4)C17—C181.370 (4)
N4—C181.375 (4)C17—C191.505 (4)
N4—H4N0.8800C18—H180.9500
N5—C201.353 (4)C19—C201.516 (4)
N5—N61.385 (3)C19—H19A0.9900
N5—H5n0.8800C19—H19B0.9900
N6—C211.303 (4)C21—C231.468 (4)
C1—C21.390 (5)C21—C221.496 (4)
C1—C61.412 (4)C22—H22A0.9800
C2—C31.388 (5)C22—H22B0.9800
C2—H20.9500C22—H22C0.9800
C3—C41.404 (5)C23—C281.408 (4)
C3—H30.9500C23—C241.418 (4)
C4—C51.386 (5)C24—C251.394 (4)
C4—H40.9500C25—C261.393 (4)
C5—C61.404 (4)C25—H250.9500
C5—H50.9500C26—C271.398 (4)
C6—C71.444 (4)C27—C281.375 (4)
C7—C81.366 (4)C27—H270.9500
C7—C91.495 (4)C28—H280.9500
C8—H80.9500
C24—O3—H3O109.5C11—C12—H12121.4
C26—O4—H4O109.5C12—C13—C14121.9 (3)
C8—N1—C1109.5 (3)C12—C13—H13119.0
C8—N1—H1N125.3C14—C13—H13119.0
C1—N1—H1N125.3C15—C14—C13120.9 (3)
C10—N2—N3121.9 (3)C15—C14—H14119.5
C10—N2—H2N119.1C13—C14—H14119.5
N3—N2—H2N119.1C14—C15—C16118.5 (3)
N2—N3—H3n109.5C14—C15—H15120.8
N2—N3—H3n1109.5C16—C15—H15120.8
H3n—N3—H3n1109.5C15—C16—C11119.7 (3)
C11—N4—C18109.0 (3)C15—C16—C17133.5 (3)
C11—N4—H4N125.5C11—C16—C17106.7 (3)
C18—N4—H4N125.5C18—C17—C16106.4 (3)
C20—N5—N6117.6 (2)C18—C17—C19127.6 (3)
C20—N5—H5121.2C16—C17—C19126.0 (3)
N6—N5—H5n121.2C17—C18—N4110.2 (3)
C21—N6—N5118.1 (3)C17—C18—H18124.9
N1—C1—C2129.9 (3)N4—C18—H18124.9
N1—C1—C6107.2 (3)C17—C19—C20111.0 (2)
C2—C1—C6122.8 (3)C17—C19—H19A109.4
C3—C2—C1116.9 (3)C20—C19—H19A109.4
C3—C2—H2121.5C17—C19—H19B109.4
C1—C2—H2121.5C20—C19—H19B109.4
C2—C3—C4121.3 (3)H19A—C19—H19B108.0
C2—C3—H3119.4O2—C20—N5122.3 (3)
C4—C3—H3119.4O2—C20—C19122.2 (3)
C5—C4—C3121.6 (3)N5—C20—C19115.5 (3)
C5—C4—H4119.2N6—C21—C23115.7 (3)
C3—C4—H4119.2N6—C21—C22124.1 (3)
C4—C5—C6118.2 (3)C23—C21—C22120.2 (2)
C4—C5—H5120.9C21—C22—H22A109.5
C6—C5—H5120.9C21—C22—H22B109.5
C5—C6—C1119.2 (3)H22A—C22—H22B109.5
C5—C6—C7133.9 (3)C21—C22—H22C109.5
C1—C6—C7106.8 (3)H22A—C22—H22C109.5
C8—C7—C6106.3 (3)H22B—C22—H22C109.5
C8—C7—C9126.7 (3)C28—C23—C24117.5 (3)
C6—C7—C9127.0 (3)C28—C23—C21120.5 (3)
N1—C8—C7110.1 (3)C24—C23—C21121.9 (3)
N1—C8—H8124.9O3—C24—C25116.4 (3)
C7—C8—H8124.9O3—C24—C23122.9 (3)
C7—C9—C10112.7 (3)C25—C24—C23120.7 (3)
C7—C9—H9A109.0C26—C25—C24119.8 (3)
C10—C9—H9A109.0C26—C25—H25120.1
C7—C9—H9B109.0C24—C25—H25120.1
C10—C9—H9B109.0O4—C26—C25121.7 (3)
H9A—C9—H9B107.8O4—C26—C27117.8 (3)
O1—C10—N2122.5 (3)C25—C26—C27120.5 (3)
O1—C10—C9123.1 (3)C28—C27—C26119.4 (3)
N2—C10—C9114.4 (3)C28—C27—H27120.3
N4—C11—C12130.5 (3)C26—C27—H27120.3
N4—C11—C16107.7 (3)C27—C28—C23122.1 (3)
C12—C11—C16121.8 (3)C27—C28—H28119.0
C13—C12—C11117.2 (3)C23—C28—H28119.0
C13—C12—H12121.4
C20—N5—N6—C21160.9 (3)N4—C11—C16—C15178.3 (3)
C8—N1—C1—C2179.3 (3)C12—C11—C16—C150.0 (4)
C8—N1—C1—C60.7 (4)N4—C11—C16—C170.8 (3)
N1—C1—C2—C3177.5 (3)C12—C11—C16—C17179.0 (3)
C6—C1—C2—C30.9 (5)C15—C16—C17—C18177.4 (3)
C1—C2—C3—C40.2 (5)C11—C16—C17—C181.5 (3)
C2—C3—C4—C50.9 (5)C15—C16—C17—C192.8 (5)
C3—C4—C5—C60.5 (5)C11—C16—C17—C19178.3 (3)
C4—C5—C6—C10.5 (4)C16—C17—C18—N41.6 (3)
C4—C5—C6—C7177.9 (3)C19—C17—C18—N4178.1 (3)
N1—C1—C6—C5177.4 (3)C11—N4—C18—C171.1 (3)
C2—C1—C6—C51.3 (5)C18—C17—C19—C2015.5 (4)
N1—C1—C6—C70.6 (3)C16—C17—C19—C20164.1 (3)
C2—C1—C6—C7179.3 (3)N6—N5—C20—O27.4 (4)
C5—C6—C7—C8177.3 (3)N6—N5—C20—C19175.0 (2)
C1—C6—C7—C80.3 (3)C17—C19—C20—O255.8 (4)
C5—C6—C7—C92.2 (6)C17—C19—C20—N5121.9 (3)
C1—C6—C7—C9179.8 (3)N5—N6—C21—C23179.1 (2)
C1—N1—C8—C70.5 (4)N5—N6—C21—C221.1 (4)
C6—C7—C8—N10.1 (3)N6—C21—C23—C28172.4 (3)
C9—C7—C8—N1179.4 (3)C22—C21—C23—C287.8 (4)
C8—C7—C9—C1094.9 (4)N6—C21—C23—C244.4 (4)
C6—C7—C9—C1085.7 (4)C22—C21—C23—C24175.4 (3)
N3—N2—C10—O16.8 (5)C28—C23—C24—O3177.6 (3)
N3—N2—C10—C9173.5 (3)C21—C23—C24—O30.7 (4)
C7—C9—C10—O155.8 (4)C28—C23—C24—C250.8 (4)
C7—C9—C10—N2123.9 (3)C21—C23—C24—C25177.7 (3)
C18—N4—C11—C12177.9 (3)O3—C24—C25—C26177.5 (3)
C18—N4—C11—C160.2 (3)C23—C24—C25—C261.0 (4)
N4—C11—C12—C13178.5 (3)C24—C25—C26—O4177.4 (3)
C16—C11—C12—C130.7 (5)C24—C25—C26—C270.6 (5)
C11—C12—C13—C141.0 (5)O4—C26—C27—C28178.2 (3)
C12—C13—C14—C150.7 (5)C25—C26—C27—C280.2 (5)
C13—C14—C15—C160.0 (5)C26—C27—C28—C230.4 (5)
C14—C15—C16—C110.3 (4)C24—C23—C28—C270.0 (4)
C14—C15—C16—C17179.1 (3)C21—C23—C28—C27177.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···N60.841.812.544 (3)145
O4—H4o···N3i0.842.233.030 (4)158
N2—H2n···O1i0.882.193.038 (4)161
N3—H3n···O40.881.892.737 (4)162
N4—H4n···O2ii0.882.062.858 (4)150
N5—H5n···O2i0.882.453.034 (4)125
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z1/2.
 

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