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Acta Crystallogr Sect E Struct Rep Online. 2011 December 1; 67(Pt 12): o3471–o3472.
Published online 2011 November 30. doi:  10.1107/S1600536811050239
PMCID: PMC3239098
Copyright © Fun et al. 2011
N′-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl­idene]naphtho­[2,1-b]furan-2-carbohydrazide monohydrate
Hoong-Kun Fun,a*‡ Wan-Sin Loh,a§ Shridhar Malladi,b B. M. Ganesh,b and Arun M. Isloorb
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
Correspondence e-mail: hkfun/at/usm.my
‡Thomson Reuters ResearcherID: A-3561-2009.
§Thomson Reuters ResearcherID: C-7581-2009.
Received November 22, 2011; Accepted November 22, 2011.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Abstract
In the title hydrate, C23H16N4O2·H2O, the pyrazole ring is approximately planar, with a maximum deviation of 0.023 (1) Å, and makes dihedral angles of 28.63 (6) and 46.44 (7)° with the naphtho­[2,1-b]furan ring system and the benzene ring, respectively, In the crystal, O—H(...)N, O—H(...)O, N—H(...)O, N—H(...)N, C—H(...)O and C—H(...)N hydrogen bonds link the mol­ecules, forming sheets lying parallel to the ab plane. The crystal structure also features C—H(...)π inter­actions involving the centroids of the pyrazole and benzene rings.
Related literature
For the biological activity of hydrazides, hydrazones and their adducts, see: Jahagirdar et al. (1990 [triangle]); Cavier & Rips (1965 [triangle]); Silva et al. (2005 [triangle]); Eissa & Soliman (2009 [triangle]). For a related structure, see: Choi et al. (2009 [triangle]). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-67-o3471-scheme1.jpg Object name is e-67-o3471-scheme1.jpg
Crystal data
  • C23H16N4O2·H2O
  • M r = 398.41
  • Monoclinic, An external file that holds a picture, illustration, etc. Object name is e-67-o3471-efi1.jpg
  • a = 7.1383 (1) Å
  • b = 9.3928 (1) Å
  • c = 28.4200 (4) Å
  • β = 96.864 (1)°
  • V = 1891.86 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.31 × 0.25 × 0.18 mm
Data collection
  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.971, T max = 0.983
  • 21248 measured reflections
  • 5516 independent reflections
  • 3857 reflections with I > 2σ(I)
  • R int = 0.058
Refinement
  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.129
  • S = 1.03
  • 5516 reflections
  • 279 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.27 e Å−3
Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050239/hb6529sup1.cif
Click here to view.(23K, cif)
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050239/hb6529Isup2.hkl
Click here to view.(270K, hkl)
Supplementary material file. DOI: 10.1107/S1600536811050239/hb6529Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.
supplementary crystallographic information
Comment
Acidhydrazones and their condensation products possessing an azometine –NHN═ CH– proton constitute an important class of compounds for new drug development. In the past several years, numerous compounds with diverse structural features have been reported. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Hydrazides, hydrazones and their adducts have displayed diverse range of biological properties such as anti-viral (Jahagirdar et al., 1990), anti-tuberculosis (Cavier et al., 1965) and anti-inflammatory activities (Silva et al., 2005; Eissa et al., 2009). We have synthesized the title compound to study its crystal structure and evaluate its biological activities.
The title compound (Fig. 1) consists of one molecule of N'-[(E)-(3-phenyl-1H-pyrazol-4-yl)methylidene]naphtho [2,1-b]furan-2-carbohydrazide and a water molecule. The pyrazole ring (N3/N4/C15–C17) is approximately planar with a maximum deviation of 0.023 (1) Å at atom C17. This ring makes dihedral angles of 28.63 (6)° with the naphtho[2,1-b]furan ring system (O1/C1–C12; maximum deviation of 0.016 (1) Å at atom C10) and 46.44 (7)° with the benzene ring (C18–C23; maximum deviation of 0.012 (1) Å at atom C18). Bond lengths and angles are comparable to a related structure (Choi et al., 2009).
In the crystal, (Fig. 2), O1W—H1W1···N4, O1W—H2W1···O2, N3—H1N3···O2, N3—H1N3···N2, N1—H1N1···O1W C14—H14A···O1W, C16—H16A···N4 and C21—H21A···O2 hydrogen bonds (Table 1) link the molecules to form sheets parallel to the ab plane. The crystal structure is further stabilized by C—H···π interactions (Table 1) involving the centroids of pyrazole (Cg1) and benzene (Cg2) rings.
Experimental
A mixture of naphtho[2,1-b]furan-2-carbohydrazide (0.226 g, 0.001 mol) and 3-phenyl-1H-pyrazole-4-carbaldehyde (0.189 g, 0.0011 mol) was refluxed in ethanol for 4 h in the presence of a catalytic amount of acetic acid. The mixture was then cooled to room temperature and the resulting solid was filtered and dried to get the title compound. Yield: 0.28 g, 73.68%. M.p.: 524–526 K.
Refinement
The O– and N-bound hydrogen atoms were located from the difference Fourier map. N-bound hydrogen atoms were refined freely and O-bound hydrogen atoms were fixed at their found positions with a riding model with Uiso(H) = 1.2 Ueq(O) [N–H= 0.94 (2) and 0.96 (2) Å; O–H = 0.8628 and 0.8895 Å]. The remaining hydrogen atoms were positioned geometrically and were refined with a riding model with Uiso(H) = 1.2 Ueq(C) [C–H = 0.95 Å].
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis, showing the sheets parallel to the ab plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
Crystal data
C23H16N4O2·H2OF(000) = 832
Mr = 398.41Dx = 1.399 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3650 reflections
a = 7.1383 (1) Åθ = 2.3–29.5°
b = 9.3928 (1) ŵ = 0.10 mm−1
c = 28.4200 (4) ÅT = 100 K
β = 96.864 (1)°Block, colourless
V = 1891.86 (4) Å30.31 × 0.25 × 0.18 mm
Z = 4
Data collection
Bruker SMART APEXII CCD diffractometer5516 independent reflections
Radiation source: fine-focus sealed tube3857 reflections with I > 2σ(I)
graphiteRint = 0.058
[var phi] and ω scansθmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −9→10
Tmin = 0.971, Tmax = 0.983k = −13→13
21248 measured reflectionsl = −39→40
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3
5516 reflections(Δ/σ)max < 0.001
279 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
O10.43329 (14)1.04167 (12)0.06904 (4)0.0190 (2)
O20.91817 (15)1.01592 (13)0.11647 (4)0.0251 (3)
N10.65264 (19)0.90451 (14)0.13601 (4)0.0177 (3)
N20.75457 (18)0.82808 (14)0.17263 (4)0.0177 (3)
N30.93853 (18)0.49668 (15)0.27204 (5)0.0196 (3)
N40.78932 (17)0.40748 (14)0.26062 (5)0.0196 (3)
C10.3524 (2)1.12767 (17)0.03335 (5)0.0183 (3)
C20.1589 (2)1.13360 (19)0.01844 (6)0.0232 (3)
H2A0.07111.07690.03270.028*
C30.1027 (2)1.22541 (19)−0.01779 (6)0.0245 (4)
H3A−0.02751.2308−0.02940.029*
C40.2337 (2)1.31378 (18)−0.03878 (6)0.0212 (3)
C50.1705 (2)1.41189 (19)−0.07502 (6)0.0242 (4)
H5A0.03981.4178−0.08610.029*
C60.2963 (2)1.49881 (18)−0.09438 (6)0.0248 (4)
H6A0.25141.5661−0.11800.030*
C70.4909 (2)1.48864 (18)−0.07936 (6)0.0238 (3)
H7A0.57721.5474−0.09340.029*
C80.5563 (2)1.39364 (17)−0.04433 (6)0.0210 (3)
H8A0.68781.3874−0.03430.025*
C90.4303 (2)1.30561 (17)−0.02320 (5)0.0185 (3)
C100.4875 (2)1.20827 (16)0.01465 (5)0.0170 (3)
C110.6639 (2)1.17157 (17)0.04153 (5)0.0188 (3)
H11A0.78461.20950.03770.023*
C120.6241 (2)1.07205 (17)0.07342 (5)0.0175 (3)
C130.7456 (2)0.99555 (17)0.11028 (5)0.0184 (3)
C140.6704 (2)0.71368 (16)0.18341 (5)0.0167 (3)
H14A0.54970.69310.16690.020*
C150.7500 (2)0.61507 (16)0.21930 (5)0.0166 (3)
C160.9210 (2)0.61994 (17)0.24849 (5)0.0185 (3)
H16A1.00870.69650.25120.022*
C170.6738 (2)0.47933 (16)0.22852 (5)0.0168 (3)
C180.4979 (2)0.41425 (16)0.20556 (5)0.0169 (3)
C190.4996 (2)0.27495 (17)0.18791 (5)0.0197 (3)
H19A0.61220.22030.19270.024*
C200.3376 (2)0.21643 (18)0.16353 (6)0.0229 (3)
H20A0.33960.12190.15170.027*
C210.1728 (2)0.29580 (19)0.15644 (6)0.0236 (4)
H21A0.06290.25640.13910.028*
C220.1685 (2)0.43245 (18)0.17454 (5)0.0209 (3)
H22A0.05500.48620.17000.025*
C230.3301 (2)0.49127 (17)0.19929 (5)0.0187 (3)
H23A0.32590.58460.21200.022*
O1W0.25339 (16)0.83476 (13)0.13979 (4)0.0270 (3)
H1W10.25180.83800.17010.041*
H2W10.14600.86940.12510.041*
H1N31.036 (3)0.467 (3)0.2959 (9)0.064 (8)*
H1N10.523 (4)0.888 (3)0.1276 (9)0.061 (7)*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.0172 (5)0.0208 (6)0.0183 (5)−0.0003 (4)−0.0002 (4)0.0029 (4)
O20.0196 (6)0.0262 (6)0.0277 (6)−0.0049 (5)−0.0040 (4)0.0068 (5)
N10.0180 (6)0.0176 (6)0.0168 (6)−0.0007 (5)−0.0016 (5)0.0038 (5)
N20.0193 (6)0.0173 (6)0.0158 (6)0.0009 (5)−0.0011 (5)0.0011 (5)
N30.0163 (6)0.0231 (7)0.0185 (6)−0.0006 (5)−0.0014 (5)0.0028 (6)
N40.0175 (6)0.0204 (7)0.0203 (7)0.0000 (5)0.0005 (5)0.0027 (5)
C10.0208 (7)0.0189 (7)0.0150 (7)0.0015 (6)0.0013 (6)0.0009 (6)
C20.0181 (8)0.0287 (9)0.0229 (8)−0.0027 (7)0.0024 (6)0.0043 (7)
C30.0189 (8)0.0305 (9)0.0238 (8)0.0017 (7)0.0017 (6)0.0034 (7)
C40.0222 (8)0.0233 (8)0.0178 (7)0.0020 (7)0.0017 (6)0.0003 (6)
C50.0240 (8)0.0289 (9)0.0191 (8)0.0053 (7)0.0004 (6)0.0024 (7)
C60.0334 (9)0.0234 (8)0.0176 (8)0.0068 (7)0.0025 (6)0.0032 (7)
C70.0299 (9)0.0229 (8)0.0192 (8)−0.0009 (7)0.0055 (6)0.0010 (7)
C80.0238 (8)0.0203 (8)0.0193 (8)0.0000 (6)0.0047 (6)0.0010 (6)
C90.0207 (8)0.0195 (8)0.0151 (7)0.0011 (6)0.0024 (6)−0.0006 (6)
C100.0175 (7)0.0181 (7)0.0152 (7)0.0011 (6)0.0013 (5)−0.0003 (6)
C110.0173 (7)0.0194 (8)0.0195 (7)0.0003 (6)0.0011 (6)0.0002 (6)
C120.0161 (7)0.0181 (7)0.0179 (7)−0.0015 (6)0.0002 (5)−0.0006 (6)
C130.0195 (7)0.0176 (7)0.0176 (7)−0.0015 (6)−0.0004 (6)0.0001 (6)
C140.0166 (7)0.0170 (7)0.0164 (7)0.0011 (6)0.0009 (5)−0.0014 (6)
C150.0177 (7)0.0169 (7)0.0153 (7)0.0015 (6)0.0022 (5)−0.0008 (6)
C160.0180 (7)0.0202 (8)0.0173 (7)−0.0004 (6)0.0028 (6)0.0008 (6)
C170.0182 (7)0.0173 (7)0.0150 (7)0.0024 (6)0.0029 (5)−0.0001 (6)
C180.0193 (7)0.0173 (7)0.0141 (7)−0.0024 (6)0.0020 (5)0.0027 (6)
C190.0223 (8)0.0179 (8)0.0194 (8)0.0008 (6)0.0039 (6)0.0021 (6)
C200.0292 (9)0.0193 (8)0.0213 (8)−0.0066 (7)0.0075 (6)−0.0027 (6)
C210.0230 (8)0.0291 (9)0.0190 (8)−0.0091 (7)0.0035 (6)−0.0016 (7)
C220.0162 (7)0.0268 (9)0.0195 (8)−0.0004 (6)0.0015 (6)0.0003 (7)
C230.0191 (7)0.0185 (8)0.0186 (7)0.0004 (6)0.0021 (6)−0.0007 (6)
O1W0.0273 (6)0.0292 (7)0.0257 (6)0.0054 (5)0.0076 (5)0.0018 (5)
Geometric parameters (Å, °)
O1—C11.3692 (18)C8—H8A0.9500
O1—C121.3826 (17)C9—C101.433 (2)
O2—C131.2383 (18)C10—C111.435 (2)
N1—C131.3499 (19)C11—C121.356 (2)
N1—N21.3954 (17)C11—H11A0.9500
N1—H1N10.94 (2)C12—C131.466 (2)
N2—C141.2860 (19)C14—C151.443 (2)
N3—C161.336 (2)C14—H14A0.9500
N3—N41.3636 (18)C15—C161.392 (2)
N3—H1N30.96 (2)C15—C171.423 (2)
N4—C171.3372 (19)C16—H16A0.9500
C1—C101.381 (2)C17—C181.476 (2)
C1—C21.397 (2)C18—C231.393 (2)
C2—C31.366 (2)C18—C191.402 (2)
C2—H2A0.9500C19—C201.389 (2)
C3—C41.433 (2)C19—H19A0.9500
C3—H3A0.9500C20—C211.387 (2)
C4—C51.415 (2)C20—H20A0.9500
C4—C91.422 (2)C21—C221.384 (2)
C5—C61.376 (2)C21—H21A0.9500
C5—H5A0.9500C22—C231.392 (2)
C6—C71.407 (2)C22—H22A0.9500
C6—H6A0.9500C23—H23A0.9500
C7—C81.376 (2)O1W—H1W10.8628
C7—H7A0.9500O1W—H2W10.8895
C8—C91.408 (2)
C1—O1—C12105.57 (12)C12—C11—H11A126.8
C13—N1—N2118.93 (13)C10—C11—H11A126.8
C13—N1—H1N1119.8 (15)C11—C12—O1111.43 (13)
N2—N1—H1N1121.1 (15)C11—C12—C13131.48 (14)
C14—N2—N1113.00 (12)O1—C12—C13117.09 (13)
C16—N3—N4112.94 (13)O2—C13—N1124.46 (14)
C16—N3—H1N3128.8 (15)O2—C13—C12121.30 (14)
N4—N3—H1N3118.2 (15)N1—C13—C12114.24 (13)
C17—N4—N3104.65 (13)N2—C14—C15123.27 (14)
O1—C1—C10110.89 (13)N2—C14—H14A118.4
O1—C1—C2124.22 (14)C15—C14—H14A118.4
C10—C1—C2124.89 (14)C16—C15—C17104.31 (13)
C3—C2—C1116.37 (15)C16—C15—C14130.05 (14)
C3—C2—H2A121.8C17—C15—C14125.31 (14)
C1—C2—H2A121.8N3—C16—C15107.04 (14)
C2—C3—C4122.18 (15)N3—C16—H16A126.5
C2—C3—H3A118.9C15—C16—H16A126.5
C4—C3—H3A118.9N4—C17—C15111.07 (13)
C5—C4—C9118.60 (15)N4—C17—C18121.01 (14)
C5—C4—C3120.88 (15)C15—C17—C18127.84 (13)
C9—C4—C3120.51 (14)C23—C18—C19118.89 (14)
C6—C5—C4120.73 (15)C23—C18—C17120.96 (14)
C6—C5—H5A119.6C19—C18—C17120.10 (14)
C4—C5—H5A119.6C20—C19—C18120.38 (15)
C5—C6—C7120.41 (15)C20—C19—H19A119.8
C5—C6—H6A119.8C18—C19—H19A119.8
C7—C6—H6A119.8C21—C20—C19120.06 (15)
C8—C7—C6120.04 (15)C21—C20—H20A120.0
C8—C7—H7A120.0C19—C20—H20A120.0
C6—C7—H7A120.0C22—C21—C20120.04 (15)
C7—C8—C9120.71 (15)C22—C21—H21A120.0
C7—C8—H8A119.6C20—C21—H21A120.0
C9—C8—H8A119.6C21—C22—C23120.13 (15)
C8—C9—C4119.48 (14)C21—C22—H22A119.9
C8—C9—C10123.75 (14)C23—C22—H22A119.9
C4—C9—C10116.75 (14)C22—C23—C18120.45 (15)
C1—C10—C9119.27 (14)C22—C23—H23A119.8
C1—C10—C11105.79 (13)C18—C23—H23A119.8
C9—C10—C11134.91 (14)H1W1—O1W—H2W1110.0
C12—C11—C10106.30 (13)
C13—N1—N2—C14−157.33 (14)C1—O1—C12—C11−0.81 (17)
C16—N3—N4—C17−0.15 (17)C1—O1—C12—C13178.90 (13)
C12—O1—C1—C101.37 (17)N2—N1—C13—O20.8 (2)
C12—O1—C1—C2−177.96 (15)N2—N1—C13—C12−178.86 (13)
O1—C1—C2—C3−179.88 (15)C11—C12—C13—O2−0.6 (3)
C10—C1—C2—C30.9 (3)O1—C12—C13—O2179.70 (14)
C1—C2—C3—C4−1.5 (3)C11—C12—C13—N1178.97 (16)
C2—C3—C4—C5−177.51 (16)O1—C12—C13—N1−0.7 (2)
C2—C3—C4—C91.8 (3)N1—N2—C14—C15178.31 (13)
C9—C4—C5—C6−0.8 (2)N2—C14—C15—C160.5 (3)
C3—C4—C5—C6178.56 (16)N2—C14—C15—C17−171.90 (14)
C4—C5—C6—C71.8 (3)N4—N3—C16—C150.06 (17)
C5—C6—C7—C8−1.5 (3)C17—C15—C16—N30.06 (16)
C6—C7—C8—C90.1 (2)C14—C15—C16—N3−173.53 (15)
C7—C8—C9—C40.9 (2)N3—N4—C17—C150.18 (16)
C7—C8—C9—C10−177.53 (15)N3—N4—C17—C18177.03 (13)
C5—C4—C9—C8−0.6 (2)C16—C15—C17—N4−0.15 (17)
C3—C4—C9—C8−179.93 (15)C14—C15—C17—N4173.83 (14)
C5—C4—C9—C10177.97 (14)C16—C15—C17—C18−176.73 (14)
C3—C4—C9—C10−1.4 (2)C14—C15—C17—C18−2.8 (2)
O1—C1—C10—C9−179.87 (13)N4—C17—C18—C23136.78 (15)
C2—C1—C10—C9−0.5 (2)C15—C17—C18—C23−46.9 (2)
O1—C1—C10—C11−1.39 (17)N4—C17—C18—C19−45.9 (2)
C2—C1—C10—C11177.93 (15)C15—C17—C18—C19130.41 (16)
C8—C9—C10—C1179.24 (15)C23—C18—C19—C201.6 (2)
C4—C9—C10—C10.8 (2)C17—C18—C19—C20−175.76 (14)
C8—C9—C10—C111.3 (3)C18—C19—C20—C210.1 (2)
C4—C9—C10—C11−177.16 (16)C19—C20—C21—C22−1.4 (2)
C1—C10—C11—C120.84 (17)C20—C21—C22—C230.9 (2)
C9—C10—C11—C12178.97 (17)C21—C22—C23—C180.8 (2)
C10—C11—C12—O1−0.02 (18)C19—C18—C23—C22−2.1 (2)
C10—C11—C12—C13−179.69 (16)C17—C18—C23—C22175.28 (14)
Hydrogen-bond geometry (Å, °)
Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C17/C15/C16 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···N4i0.862.132.9625 (18)163
O1W—H2W1···O2ii0.892.122.9465 (16)154
N3—H1N3···O2iii0.95 (2)2.52 (3)3.2162 (18)130.4 (19)
N3—H1N3···N2iii0.95 (2)2.10 (3)2.9927 (19)155 (2)
N1—H1N1···O1W0.94 (3)2.06 (3)2.9388 (18)155 (2)
C14—H14A···O1W0.952.543.2877 (18)136
C16—H16A···N4iv0.952.503.430 (2)167
C21—H21A···O2v0.952.533.318 (2)140
C7—H7A···Cg2vi0.952.803.6022 (18)142
C22—H22A···Cg1ii0.952.933.5274 (16)122
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, y+1/2, −z+1/2; (v) x−1, y−1, z; (vi) −x+1, −y+2, −z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6529).
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