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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2563–o2564.
Published online 2010 September 15. doi:  10.1107/S1600536810036159
PMCID: PMC2983346

4-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}-N-(4-cyano­phen­yl)piperazine-1-carboxamide

Abstract

In the title compound, C28H22ClFN6O2, the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyano­phenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chloro­phenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, inter­molecular N—H(...)O, C—H(...)N and C—H(...)O hydrogen bonds link the mol­ecules into sheets parallel to the ac plane.

Related literature

For background to pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 [triangle], 2010 [triangle]). For the synthetic procedure, see: Ragavan et al. (2010 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For reference bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Fun et al. (2010 [triangle]); Shahani et al. (2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2563-scheme1.jpg

Experimental

Crystal data

  • C28H22ClFN6O2
  • M r = 528.97
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2563-efi1.jpg
  • a = 9.9221 (3) Å
  • b = 21.3339 (7) Å
  • c = 12.7201 (4) Å
  • β = 111.629 (1)°
  • V = 2502.97 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 100 K
  • 0.36 × 0.26 × 0.08 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.931, T max = 0.985
  • 19192 measured reflections
  • 5660 independent reflections
  • 4272 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.116
  • S = 1.07
  • 5660 reflections
  • 347 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.35 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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036159/wn2409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036159/wn2409Isup2.hkl

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 thanks the Malaysian government and USM for the award of a Research Fellowship. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

The antibacterial and antifungal activities of azoles have been widely studied and some of them are used in clinical practice as antimicrobial agents. However, azole-resistant strains have led to the development of new antimicrobial compounds. In particular, pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazoles form an important class of heterocyclic compound and many pyrazole derivatives are reported to have a broad spectrum of biological activities, such as anti-inflammatory, antifungal, herbicidal, antitumor, cytotoxic and antiviral activities; they are also used in molecular modelling. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists as well as kinase inhibitor for the treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of drug molecules play an important role in enhancing their biological activity, we are interested in compounds having 4-fluoro- or 4-chloro-substitution in 1,5-diaryl pyrazoles. The background to pyrazole derivatives and their microbial activities habe been reported in reccent years (Ragavan et al., 2009, 2010). The crystal structure of the title compound is reported here.

In the title compound (Fig. 1) the piperazine ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) of Q = 0.540 (2) Å, Θ = 1.3 (2)°, [var phi] = 235 (21)° and the plane through the coplanar atoms (N4/C19/N3/C17) forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyanophenyl rings. The dihedral angles formed between the pyrazole and attached fluoro- and chlorophenyl rings are 34.16 (10) and 73.27 (12)°, respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those in related crystal structures (Fun et al., 2010; Shahani et al., 2010).

In the crystal packing (Fig. 2), intermolecular N5—H1N5···O1, C2—H2A···N2, C4—H4A···O1 and C7—H7A···O2 hydrogen bonds (Table 1) link the molecules into two-dimensional sheets parallel to the ac plane.

Experimental

The compound has been synthesized using a method reported in the literature (Ragavan et al., 2010) and recrystallized using a 1:1 mixture of ethanol-chloroform. Yield = 77%. M. p. = 485.3–486 K.

Refinement

Atom H1N5 was located in a difference Fourier map and was refined freely [N—H = 0.87 (3) Å]. The remaining H atoms were positioned geometrically [C—H = 0.93 or 0.97 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C28H22ClFN6O2F(000) = 1096
Mr = 528.97Dx = 1.404 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5338 reflections
a = 9.9221 (3) Åθ = 2.4–27.3°
b = 21.3339 (7) ŵ = 0.20 mm1
c = 12.7201 (4) ÅT = 100 K
β = 111.629 (1)°Plate, colourless
V = 2502.97 (14) Å30.36 × 0.26 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5660 independent reflections
Radiation source: fine-focus sealed tube4272 reflections with I > 2σ(I)
graphiteRint = 0.037
[var phi] and ω scansθmax = 27.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→11
Tmin = 0.931, Tmax = 0.985k = −27→24
19192 measured reflectionsl = −14→16

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0294P)2 + 2.8225P] where P = (Fo2 + 2Fc2)/3
5660 reflections(Δ/σ)max < 0.001
347 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.35 e Å3

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
Cl10.47534 (7)0.60803 (3)0.78980 (5)0.03029 (16)
F10.48142 (15)0.22562 (7)0.89619 (12)0.0304 (3)
N10.81146 (19)0.34593 (9)0.69103 (14)0.0161 (4)
N20.89747 (19)0.31063 (9)0.65254 (14)0.0164 (4)
N31.04762 (19)0.34908 (9)0.44459 (14)0.0174 (4)
N41.0136 (2)0.35012 (9)0.21385 (15)0.0203 (4)
N51.1177 (2)0.35113 (10)0.07780 (16)0.0194 (4)
N61.2635 (2)0.45747 (11)−0.37105 (17)0.0335 (5)
O11.14153 (16)0.28689 (7)0.59902 (12)0.0193 (3)
O20.91589 (17)0.41027 (8)0.05706 (13)0.0236 (4)
C10.7918 (2)0.29390 (11)0.85563 (18)0.0197 (5)
H1A0.89050.29990.89480.024*
C20.7083 (2)0.26399 (11)0.90742 (19)0.0220 (5)
H2A0.74930.25030.98190.026*
C30.5637 (2)0.25525 (11)0.84547 (19)0.0216 (5)
C40.4962 (2)0.27504 (11)0.73509 (19)0.0228 (5)
H4A0.39780.26810.69590.027*
C50.5800 (2)0.30562 (11)0.68465 (18)0.0203 (5)
H5A0.53800.32000.61060.024*
C60.7266 (2)0.31466 (10)0.74509 (18)0.0163 (5)
C70.7134 (2)0.45597 (11)0.79798 (18)0.0209 (5)
H7A0.75930.42460.84940.025*
C80.6372 (2)0.50256 (11)0.82822 (19)0.0227 (5)
H8A0.63030.50210.89920.027*
C90.5715 (2)0.54962 (11)0.75187 (19)0.0213 (5)
C100.5806 (2)0.55132 (11)0.64628 (19)0.0218 (5)
H10A0.53650.58350.59610.026*
C110.6562 (2)0.50443 (11)0.61567 (18)0.0194 (5)
H11A0.66290.50540.54470.023*
C120.7220 (2)0.45589 (11)0.69021 (18)0.0177 (5)
C130.8020 (2)0.40700 (11)0.65574 (17)0.0166 (5)
C140.8854 (2)0.41079 (11)0.58986 (17)0.0176 (5)
H14A0.90070.44600.55260.021*
C150.9423 (2)0.35043 (11)0.59080 (17)0.0163 (5)
C161.0502 (2)0.32613 (10)0.54447 (17)0.0157 (4)
C171.1727 (2)0.33981 (11)0.41143 (18)0.0192 (5)
H17A1.24160.31200.46520.023*
H17B1.22040.37970.41340.023*
C181.1283 (2)0.31192 (11)0.29329 (17)0.0205 (5)
H18A1.21120.31070.27030.025*
H18B1.09390.26940.29340.025*
C190.8884 (2)0.35880 (11)0.24632 (18)0.0202 (5)
H19A0.84190.31870.24490.024*
H19B0.81890.38610.19210.024*
C200.9325 (2)0.38715 (11)0.36402 (17)0.0195 (5)
H20A0.96680.42970.36340.023*
H20B0.84930.38860.38670.023*
C211.0089 (2)0.37302 (11)0.11281 (18)0.0179 (5)
C221.1497 (2)0.37577 (11)−0.01271 (17)0.0185 (5)
C231.2352 (3)0.33979 (11)−0.05514 (19)0.0235 (5)
H23A1.26880.3009−0.02300.028*
C241.2707 (3)0.36094 (12)−0.1441 (2)0.0261 (5)
H24A1.32680.3361−0.17220.031*
C251.2229 (2)0.41924 (11)−0.19194 (18)0.0204 (5)
C261.1417 (3)0.45604 (12)−0.1474 (2)0.0255 (5)
H26A1.11150.4956−0.17750.031*
C271.1050 (3)0.43481 (11)−0.0591 (2)0.0247 (5)
H27A1.05020.4600−0.03040.030*
C281.2494 (3)0.44038 (12)−0.29033 (19)0.0242 (5)
H1N51.148 (3)0.3133 (14)0.098 (2)0.033 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0278 (3)0.0295 (4)0.0347 (3)0.0067 (3)0.0129 (3)−0.0071 (3)
F10.0281 (8)0.0372 (9)0.0311 (8)−0.0038 (7)0.0170 (6)0.0075 (7)
N10.0167 (9)0.0172 (10)0.0156 (9)0.0006 (8)0.0074 (7)0.0003 (8)
N20.0161 (9)0.0184 (10)0.0156 (9)−0.0001 (8)0.0069 (7)−0.0017 (8)
N30.0154 (9)0.0217 (10)0.0151 (9)0.0004 (8)0.0056 (7)0.0006 (8)
N40.0192 (10)0.0268 (11)0.0163 (9)0.0060 (8)0.0081 (7)0.0040 (8)
N50.0244 (11)0.0174 (11)0.0190 (9)0.0042 (9)0.0110 (8)0.0024 (8)
N60.0404 (13)0.0391 (14)0.0255 (11)−0.0110 (11)0.0175 (10)−0.0008 (10)
O10.0193 (8)0.0207 (9)0.0175 (8)0.0024 (7)0.0063 (6)0.0022 (7)
O20.0264 (9)0.0278 (10)0.0190 (8)0.0088 (7)0.0111 (7)0.0068 (7)
C10.0176 (11)0.0217 (13)0.0187 (11)0.0025 (9)0.0055 (9)0.0024 (9)
C20.0236 (12)0.0258 (14)0.0167 (11)0.0039 (10)0.0076 (9)0.0062 (10)
C30.0255 (13)0.0209 (13)0.0237 (11)−0.0025 (10)0.0153 (10)0.0007 (10)
C40.0152 (11)0.0278 (14)0.0241 (12)−0.0018 (10)0.0058 (9)−0.0017 (10)
C50.0214 (12)0.0241 (13)0.0148 (10)0.0016 (10)0.0060 (9)0.0011 (10)
C60.0191 (11)0.0147 (11)0.0176 (10)0.0008 (9)0.0096 (9)−0.0004 (9)
C70.0233 (12)0.0220 (13)0.0165 (10)0.0017 (10)0.0062 (9)−0.0002 (10)
C80.0253 (12)0.0255 (13)0.0190 (11)−0.0005 (10)0.0102 (9)−0.0040 (10)
C90.0162 (11)0.0194 (12)0.0279 (12)−0.0015 (9)0.0076 (9)−0.0064 (10)
C100.0188 (12)0.0188 (13)0.0262 (12)0.0011 (10)0.0063 (9)0.0028 (10)
C110.0179 (11)0.0211 (13)0.0189 (10)−0.0033 (9)0.0064 (8)−0.0005 (9)
C120.0167 (11)0.0170 (12)0.0198 (10)−0.0033 (9)0.0073 (8)−0.0043 (9)
C130.0172 (11)0.0173 (12)0.0131 (10)−0.0010 (9)0.0030 (8)−0.0008 (9)
C140.0192 (11)0.0181 (12)0.0163 (10)−0.0030 (9)0.0076 (9)−0.0009 (9)
C150.0167 (11)0.0185 (12)0.0124 (10)−0.0027 (9)0.0038 (8)−0.0016 (9)
C160.0160 (11)0.0164 (12)0.0139 (10)−0.0046 (9)0.0045 (8)−0.0041 (9)
C170.0164 (11)0.0245 (13)0.0170 (10)−0.0016 (9)0.0066 (9)0.0003 (10)
C180.0201 (12)0.0274 (13)0.0154 (10)0.0049 (10)0.0083 (9)0.0025 (10)
C190.0177 (11)0.0265 (13)0.0165 (10)0.0026 (10)0.0064 (9)0.0027 (10)
C200.0192 (11)0.0226 (13)0.0176 (10)0.0035 (10)0.0080 (9)0.0020 (9)
C210.0185 (11)0.0184 (12)0.0164 (10)−0.0021 (9)0.0060 (9)−0.0023 (9)
C220.0207 (12)0.0224 (13)0.0119 (10)−0.0030 (10)0.0056 (8)−0.0028 (9)
C230.0296 (13)0.0205 (13)0.0227 (11)0.0054 (10)0.0124 (10)0.0034 (10)
C240.0289 (13)0.0304 (15)0.0233 (12)0.0052 (11)0.0146 (10)−0.0003 (11)
C250.0220 (12)0.0234 (13)0.0161 (10)−0.0040 (10)0.0076 (9)−0.0015 (9)
C260.0349 (14)0.0199 (13)0.0250 (12)0.0020 (11)0.0150 (10)0.0028 (10)
C270.0339 (14)0.0200 (13)0.0259 (12)0.0034 (11)0.0179 (11)0.0004 (10)
C280.0252 (13)0.0265 (14)0.0203 (12)−0.0063 (10)0.0077 (10)−0.0034 (10)

Geometric parameters (Å, °)

Cl1—C91.742 (2)C8—H8A0.9300
F1—C31.367 (2)C9—C101.379 (3)
N1—N21.358 (2)C10—C111.389 (3)
N1—C131.370 (3)C10—H10A0.9300
N1—C61.433 (3)C11—C121.393 (3)
N2—C151.339 (3)C11—H11A0.9300
N3—C161.353 (3)C12—C131.472 (3)
N3—C171.464 (3)C13—C141.380 (3)
N3—C201.467 (3)C14—C151.405 (3)
N4—C211.360 (3)C14—H14A0.9300
N4—C191.458 (3)C15—C161.492 (3)
N4—C181.460 (3)C17—C181.523 (3)
N5—C211.392 (3)C17—H17A0.9700
N5—C221.404 (3)C17—H17B0.9700
N5—H1N50.87 (3)C18—H18A0.9700
N6—C281.146 (3)C18—H18B0.9700
O1—C161.241 (3)C19—C201.522 (3)
O2—C211.226 (3)C19—H19A0.9700
C1—C61.386 (3)C19—H19B0.9700
C1—C21.389 (3)C20—H20A0.9700
C1—H1A0.9300C20—H20B0.9700
C2—C31.372 (3)C22—C231.392 (3)
C2—H2A0.9300C22—C271.392 (3)
C3—C41.380 (3)C23—C241.380 (3)
C4—C51.386 (3)C23—H23A0.9300
C4—H4A0.9300C24—C251.389 (3)
C5—C61.386 (3)C24—H24A0.9300
C5—H5A0.9300C25—C261.387 (3)
C7—C81.387 (3)C25—C281.443 (3)
C7—C121.404 (3)C26—C271.378 (3)
C7—H7A0.9300C26—H26A0.9300
C8—C91.382 (3)C27—H27A0.9300
N2—N1—C13112.69 (17)C15—C14—H14A127.2
N2—N1—C6118.25 (17)N2—C15—C14111.51 (18)
C13—N1—C6128.21 (18)N2—C15—C16116.95 (19)
C15—N2—N1104.40 (17)C14—C15—C16131.30 (19)
C16—N3—C17119.79 (18)O1—C16—N3121.78 (19)
C16—N3—C20126.63 (18)O1—C16—C15119.71 (18)
C17—N3—C20113.48 (17)N3—C16—C15118.49 (19)
C21—N4—C19119.10 (18)N3—C17—C18111.66 (17)
C21—N4—C18126.94 (18)N3—C17—H17A109.3
C19—N4—C18113.76 (17)C18—C17—H17A109.3
C21—N5—C22125.0 (2)N3—C17—H17B109.3
C21—N5—H1N5116.6 (18)C18—C17—H17B109.3
C22—N5—H1N5115.4 (18)H17A—C17—H17B108.0
C6—C1—C2119.4 (2)N4—C18—C17109.47 (18)
C6—C1—H1A120.3N4—C18—H18A109.8
C2—C1—H1A120.3C17—C18—H18A109.8
C3—C2—C1118.1 (2)N4—C18—H18B109.8
C3—C2—H2A121.0C17—C18—H18B109.8
C1—C2—H2A121.0H18A—C18—H18B108.2
F1—C3—C2118.2 (2)N4—C19—C20111.31 (18)
F1—C3—C4118.1 (2)N4—C19—H19A109.4
C2—C3—C4123.7 (2)C20—C19—H19A109.4
C3—C4—C5117.8 (2)N4—C19—H19B109.4
C3—C4—H4A121.1C20—C19—H19B109.4
C5—C4—H4A121.1H19A—C19—H19B108.0
C6—C5—C4119.7 (2)N3—C20—C19109.55 (18)
C6—C5—H5A120.2N3—C20—H20A109.8
C4—C5—H5A120.2C19—C20—H20A109.8
C5—C6—C1121.3 (2)N3—C20—H20B109.8
C5—C6—N1118.75 (19)C19—C20—H20B109.8
C1—C6—N1119.91 (19)H20A—C20—H20B108.2
C8—C7—C12120.5 (2)O2—C21—N4122.4 (2)
C8—C7—H7A119.8O2—C21—N5122.7 (2)
C12—C7—H7A119.8N4—C21—N5114.94 (19)
C9—C8—C7119.3 (2)C23—C22—C27118.6 (2)
C9—C8—H8A120.3C23—C22—N5117.7 (2)
C7—C8—H8A120.3C27—C22—N5123.6 (2)
C10—C9—C8121.4 (2)C24—C23—C22121.0 (2)
C10—C9—Cl1119.32 (18)C24—C23—H23A119.5
C8—C9—Cl1119.31 (18)C22—C23—H23A119.5
C9—C10—C11119.3 (2)C23—C24—C25120.2 (2)
C9—C10—H10A120.3C23—C24—H24A119.9
C11—C10—H10A120.3C25—C24—H24A119.9
C10—C11—C12120.7 (2)C26—C25—C24119.0 (2)
C10—C11—H11A119.7C26—C25—C28119.8 (2)
C12—C11—H11A119.7C24—C25—C28121.2 (2)
C11—C12—C7118.8 (2)C27—C26—C25121.0 (2)
C11—C12—C13119.52 (19)C27—C26—H26A119.5
C7—C12—C13121.7 (2)C25—C26—H26A119.5
N1—C13—C14105.71 (19)C26—C27—C22120.3 (2)
N1—C13—C12123.74 (19)C26—C27—H27A119.9
C14—C13—C12130.5 (2)C22—C27—H27A119.9
C13—C14—C15105.69 (19)N6—C28—C25176.8 (3)
C13—C14—H14A127.2
C13—N1—N2—C15−0.5 (2)C13—C14—C15—N20.4 (2)
C6—N1—N2—C15169.86 (18)C13—C14—C15—C16−173.7 (2)
C6—C1—C2—C31.1 (3)C17—N3—C16—O1−14.7 (3)
C1—C2—C3—F1179.8 (2)C20—N3—C16—O1169.2 (2)
C1—C2—C3—C4−0.7 (4)C17—N3—C16—C15163.51 (19)
F1—C3—C4—C5179.3 (2)C20—N3—C16—C15−12.6 (3)
C2—C3—C4—C5−0.2 (4)N2—C15—C16—O1−33.1 (3)
C3—C4—C5—C60.7 (3)C14—C15—C16—O1140.7 (2)
C4—C5—C6—C1−0.2 (3)N2—C15—C16—N3148.6 (2)
C4—C5—C6—N1179.5 (2)C14—C15—C16—N3−37.6 (3)
C2—C1—C6—C5−0.7 (3)C16—N3—C17—C18128.3 (2)
C2—C1—C6—N1179.6 (2)C20—N3—C17—C18−55.1 (3)
N2—N1—C6—C5−102.4 (2)C21—N4—C18—C17130.4 (2)
C13—N1—C6—C566.2 (3)C19—N4—C18—C17−54.9 (2)
N2—N1—C6—C177.3 (3)N3—C17—C18—N453.1 (2)
C13—N1—C6—C1−114.1 (2)C21—N4—C19—C20−128.6 (2)
C12—C7—C8—C9−1.1 (3)C18—N4—C19—C2056.3 (3)
C7—C8—C9—C10−0.2 (4)C16—N3—C20—C19−129.4 (2)
C7—C8—C9—Cl1179.84 (18)C17—N3—C20—C1954.4 (2)
C8—C9—C10—C110.6 (3)N4—C19—C20—N3−53.7 (2)
Cl1—C9—C10—C11−179.42 (17)C19—N4—C21—O213.6 (3)
C9—C10—C11—C120.3 (3)C18—N4—C21—O2−172.0 (2)
C10—C11—C12—C7−1.5 (3)C19—N4—C21—N5−166.6 (2)
C10—C11—C12—C13−179.7 (2)C18—N4—C21—N57.9 (3)
C8—C7—C12—C111.9 (3)C22—N5—C21—O211.2 (3)
C8—C7—C12—C13−179.9 (2)C22—N5—C21—N4−168.7 (2)
N2—N1—C13—C140.7 (2)C21—N5—C22—C23−164.2 (2)
C6—N1—C13—C14−168.42 (19)C21—N5—C22—C2718.1 (3)
N2—N1—C13—C12−176.73 (18)C27—C22—C23—C24−2.4 (4)
C6—N1—C13—C1214.1 (3)N5—C22—C23—C24179.8 (2)
C11—C12—C13—N1−148.1 (2)C22—C23—C24—C250.9 (4)
C7—C12—C13—N133.7 (3)C23—C24—C25—C261.2 (4)
C11—C12—C13—C1435.1 (3)C23—C24—C25—C28−175.3 (2)
C7—C12—C13—C14−143.0 (2)C24—C25—C26—C27−1.8 (4)
N1—C13—C14—C15−0.6 (2)C28—C25—C26—C27174.8 (2)
C12—C13—C14—C15176.6 (2)C25—C26—C27—C220.2 (4)
N1—N2—C15—C140.0 (2)C23—C22—C27—C261.8 (3)
N1—N2—C15—C16175.01 (17)N5—C22—C27—C26179.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N5—H1N5···O1i0.87 (3)2.14 (3)2.958 (3)157 (2)
C2—H2A···N2ii0.932.493.386 (3)161
C4—H4A···O1iii0.932.423.310 (3)161
C7—H7A···O2iv0.932.543.312 (3)140

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2409).

References

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