N′-(4-Ethyl­cyclo­hexyl­idene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

Akkurt, M.; Çelikesir, S.T.; Üstündağ, G.C.; Çapan, G.; Büyükgüngör, O.

doi:10.1107/S1600536813020394

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1331

doi:10.1107/S1600536813020394

Open

access

N′-(4-Ethylcyclohexylidene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

Mehmet Akkurt,^a ^* Sevim Türktekin Çelikesir,^a Gökçe Cihan Üstündağ,^b Gültaze Çapan ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 22 July 2013; accepted 23 July 2013; online 27 July 2013)

The title compound, C₂₃H₂₄FN₃O, crystallizes with two independent molecules (I and II) in the asymmetric unit. These pairs of molecules are linked to each other as N—H⋯O dimers with an R₂²(10) motif. Furthermore, the crystal structure also exhibits C—H⋯π interactions. The atoms of the ethyl group in molecule I are disordered over two sites with an occupancy ratio of 0.817 (6):0.183 (6).

Related literature

For the antitubercular and antiviral activity of variously substituted N-(1-thia-4-azaspiro[4.5]dec-4-yl)carboxamides, see: Cihan-Üstündağ & Çapan (2012 ); Göktas et al. (2012 ). For similar structures, see: Çelikesir et al. (2013a ,b ). For puckering analysis, see: Cremer & Pople (1975 ). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₂₄FN₃O
M_r = 377.45
Triclinic, $[P \overline 1]$
a = 11.8121 (5) Å
b = 13.3802 (5) Å
c = 15.5693 (6) Å
α = 114.328 (3)°
β = 95.642 (3)°
γ = 110.434 (3)°
V = 2014.85 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.55 × 0.48 × 0.37 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.955, T_max = 0.969
30678 measured reflections
8272 independent reflections
5564 reflections with I > 2σ(I)
R_int = 0.108

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.180
S = 1.02
8272 reflections
528 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.85 (3)	2.00 (3)	2.836 (3)	168 (3)
N4—H4N⋯O1	0.85 (3)	2.08 (3)	2.887 (3)	160 (2)
C9—H9⋯Cg1ⁱ	0.93	2.81	3.636 (3)	149
C17—H17A⋯Cg3	0.97	2.87	3.820 (3)	165
C40—H40A⋯Cg7	0.97	2.79	3.727 (4)	163
C40—H40B⋯Cg5ⁱⁱ	0.97	2.65	3.595 (4)	163
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813020394/sj5346sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020394/sj5346Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020394/sj5346Isup3.cml

checkCIF report

Comment top

On reaction with mercaptoalkanoic acids, cyclohexylidenehydrazides smoothly afford N-(1-thia-3-oxo-4-azaspiro[4.5]dec-4-yl)carboxamides with promising antituberculosis (Cihan-Üstündağ & Çapan, 2012) and antiviral (Göktas et al., 2012) activity. We have recently reported on the crystal structures of two such precursors (Türktekin-Çelikesir et al., 2013a,b). We herein report the X-ray diffraction analysis of the title compound.

In the title compound, (Fig. 1), the asymmetric unit contains two crystallographically independently molecules whose cyclohexane rings adopt chair conformations [the puckering parameters (Cremer & Pople, 1975) are Q_T = 0.507 (4) Å, θ = 4.0 (6)°, ϕ = 277 (7)° for molecule I (with N1), and Q_T = 0.531 (4) Å, θ = 12.5 (4) °, ϕ = 205.2 (18) ° for molecule II (with N4)].

The indole ring systems of both molecules I and II are essentially planar [maximum deviations are 0.026 (4) Å for C3 in molecule I and 0.028 (2) Å for C30 in molecule II]. The indole ring systems of molecules I and II make dihedral angles of 77.93 (12) and 77.66 (14)° with their phenyl rings, respectively.

In the crystal, pairs of molecules I and II in the asymmetric unit are linked to each other, forming N—H···O dimers (Table 1, Fig. 2), with the R₂²(10) ring motif (Bernstein et al., 1995). In addition, C—H···π interactions (Table 1) contribute to the stabilization of the crystal structure.

Related literature top

For the antitubercular and antiviral activity of variously substituted N-(1-thia-4-azaspiro[4.5]dec-4-yl)carboxamides, see: Cihan-Üstündağ & Çapan (2012); Göktas et al. (2012). For similar structures, see: Çelikesir et al. (2013a,b). For puckering analysis, see: Cremer & Pople (1975). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

A mixture of 5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (0.005 mol) and 4-ethyl cyclohexanone (0.007 mol) was refluxed in 15 ml absolute ethanol for 5 h. The precipitate obtained on cooling was purified by recrystallization from an ethanol-water mixture to afford colorless prisms.

[Yield: 79%, m.p.: 451.0- 452.5 K]. IR(KBr): υ_max 3346, 3235 (N—H), 1654 (C=O) cm^{-1. 1}H-NMR (DMSO-d₆/500 MHz): δ 0.84 (t, 3H, J= 7.2 Hz, 4-CH₂CH₃-cyc.*), 1.13 (br. d, 1H,J=6.8 Hz, CH/CH₂-cyc.), 1.19 (br. t, 2H, J=6.6 Hz, 4-CH₂CH₃-cyc.), 1.33 (s, 1H, CH/ CH₂-cyc.), 1.48 (br. s, 1H, CH/CH₂-cyc.), 1.61 (d, 2H, J=12.7 Hz, CH/CH₂-cyc.), 1.70–1.90 (m, 2H, CH/CH₂-cyc.), 2.13 (s, 1H, CH/CH₂-cyc.), 2.30 (s, 1H, CH/CH₂-cyc.), 7.12 (br. t, 2H, J= 8.8 Hz, H4, H6-ind.), 7.42–7.51 (m, 6H, H7, 3-C₆H₅-ind.), 9.44 (s, 1H, CONH), 12.03 (s, 1H, NH) p.p.m.. ¹³C-NMR(APT, DMSO-d₆/125 MHz): δ 12.12 (4-CH₂CH₃-cyc.), 26.06 (CH₂-cyc.), 28.79 (4-CH₂CH₃-cyc.), 31.88 (CH₂-cyc.), 32.86 (CH₂-cyc.), 34.65 (CH₂-cyc.), 38.32 (CH-cyc.), 104.64 (d, J=23.5 Hz, C4-ind.), 113.50 (d, C6-ind.), 114.40 (C7-ind.), 118.00 (C3-ind.), 126.80 (C3a-ind.), 128.54 (3-C₆H₅ (C4)-ind.), 129.68 (3-C₆H₅(C3,C5)-ind.), 129.91 (C2-ind.), 130.90 (3-C₆H₅(C2,C6)-ind.), 133.03** (C7a-ind.), 134.02** (3-C₆H₅(C1)-ind.), 158.24 (C=N), 158.30 (d, J=233.6 Hz, C5-ind.), 162.11 (C=O) p.p.m.. MS (APCI+) m/z (%) 378 ((M+H)⁺, 100), (APCI–) m/z (%) 376 ((M—H)^-, 100). Analysis calculated for C₂₃H₂₄FN₃O: C 73.19, H 6.41, N 11.13%. Found: C 72.84, H 6.68, N 10.93%.(*cyc.=cyclohexylidene, br.=broad, ind.=indole, **interchangeable).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the pairs of molecules I and II of the title compound in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. View of the N—H···O dimer between the pairs of molecules I and II in the asymmetric unit. H atoms not participating in hydrogen bonding have been omitted for clarity.

N'-(4-Ethylcyclohexylidene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide top

Crystal data top

C₂₃H₂₄FN₃O	Z = 4
M_r = 377.45	F(000) = 800
Triclinic, P1	D_x = 1.244 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.8121 (5) Å	Cell parameters from 34554 reflections
b = 13.3802 (5) Å	θ = 2.0–27.3°
c = 15.5693 (6) Å	µ = 0.08 mm⁻¹
α = 114.328 (3)°	T = 296 K
β = 95.642 (3)°	Prism, colourless
γ = 110.434 (3)°	0.55 × 0.48 × 0.37 mm
V = 2014.85 (17) Å³

Data collection top

Stoe IPDS 2 diffractometer	8272 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5564 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.108
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.3°
ω–scans	h = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
T_min = 0.955, T_max = 0.969	l = −19→19
30678 measured reflections

Refinement top

Refinement on F²	8 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.067	W = 1/[Σ²(FO²) + (0.083P)² + 0.3779P] WHERE P = (FO² + 2FC²)/3
wR(F²) = 0.180	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.35 e Å⁻³
8272 reflections	Δρ_min = −0.19 e Å⁻³
528 parameters

Crystal data top

C₂₃H₂₄FN₃O	γ = 110.434 (3)°
M_r = 377.45	V = 2014.85 (17) Å³
Triclinic, P1	Z = 4
a = 11.8121 (5) Å	Mo Kα radiation
b = 13.3802 (5) Å	µ = 0.08 mm⁻¹
c = 15.5693 (6) Å	T = 296 K
α = 114.328 (3)°	0.55 × 0.48 × 0.37 mm
β = 95.642 (3)°

Data collection top

Stoe IPDS 2 diffractometer	8272 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	5564 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.969	R_int = 0.108
30678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	8 restraints
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.35 e Å⁻³
8272 reflections	Δρ_min = −0.19 e Å⁻³
528 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1	0.05143 (16)	−0.22445 (17)	0.21734 (13)	0.0940 (6)
O1	0.59795 (19)	0.40150 (17)	0.65907 (12)	0.0752 (7)
N1	0.3715 (2)	0.2028 (2)	0.53565 (15)	0.0612 (7)
N2	0.7073 (2)	0.3010 (2)	0.58120 (15)	0.0662 (8)
N3	0.8220 (2)	0.3863 (2)	0.65017 (14)	0.0699 (8)
C1	0.2761 (2)	0.0988 (2)	0.46077 (16)	0.0578 (8)
C2	0.1458 (3)	0.0503 (3)	0.4466 (2)	0.0717 (10)
C3	0.0724 (3)	−0.0574 (3)	0.3636 (2)	0.0743 (10)
C4	0.1284 (3)	−0.1150 (3)	0.29687 (19)	0.0686 (9)
C5	0.2541 (2)	−0.0691 (2)	0.30711 (17)	0.0623 (8)
C6	0.3310 (2)	0.0409 (2)	0.39164 (16)	0.0542 (8)
C7	0.4643 (2)	0.1138 (2)	0.42771 (15)	0.0524 (7)
C8	0.5555 (2)	0.0856 (2)	0.37421 (15)	0.0521 (7)
C9	0.5933 (3)	−0.0018 (2)	0.3731 (2)	0.0710 (10)
C10	0.6731 (3)	−0.0321 (3)	0.3197 (2)	0.0847 (11)
C11	0.7165 (3)	0.0241 (3)	0.2664 (2)	0.0914 (12)
C12	0.6810 (3)	0.1118 (4)	0.2665 (2)	0.0949 (14)
C13	0.6016 (3)	0.1429 (3)	0.3202 (2)	0.0717 (10)
C14	0.4853 (2)	0.2117 (2)	0.51692 (16)	0.0547 (8)
C15	0.6011 (2)	0.3143 (2)	0.59215 (16)	0.0577 (8)
C16	0.9194 (3)	0.3713 (3)	0.63047 (18)	0.0691 (9)
C17	0.9279 (3)	0.2770 (3)	0.5408 (2)	0.0833 (11)
C18	1.0327 (4)	0.3371 (4)	0.5030 (3)	0.1061 (18)
C19	1.1560 (3)	0.4280 (4)	0.5781 (3)	0.1004 (16)
C20	1.1385 (3)	0.5181 (4)	0.6656 (3)	0.1005 (16)
C21	1.0427 (3)	0.4600 (3)	0.7075 (2)	0.0902 (11)
C22A	1.2593 (5)	0.4974 (5)	0.5436 (4)	0.110 (2)	0.817 (6)
C23A	1.3041 (6)	0.4198 (6)	0.4711 (5)	0.126 (3)	0.817 (6)
C23B	1.366 (2)	0.508 (2)	0.537 (2)	0.126 (3)	0.183 (6)
C22B	1.2352 (13)	0.4138 (18)	0.5038 (15)	0.110 (2)	0.183 (6)
F2	0.6710 (2)	1.04361 (17)	0.94884 (19)	0.1217 (9)
O2	0.31889 (19)	0.31546 (16)	0.71583 (12)	0.0730 (6)
N4	0.4818 (2)	0.5522 (2)	0.76600 (14)	0.0581 (7)
N5	0.2973 (2)	0.37572 (19)	0.86894 (15)	0.0569 (7)
N6	0.21921 (19)	0.26057 (17)	0.85033 (14)	0.0580 (7)
C24	0.5392 (2)	0.6749 (2)	0.80253 (17)	0.0586 (8)
C25	0.6219 (3)	0.7449 (3)	0.7690 (2)	0.0719 (10)
C26	0.6642 (3)	0.8682 (3)	0.8203 (2)	0.0820 (11)
C27	0.6270 (3)	0.9203 (3)	0.9024 (3)	0.0831 (11)
C28	0.5475 (3)	0.8556 (3)	0.9381 (2)	0.0725 (10)
C29	0.5031 (2)	0.7290 (2)	0.88695 (17)	0.0569 (8)
C30	0.4220 (2)	0.6328 (2)	0.90166 (15)	0.0529 (7)
C31	0.3655 (2)	0.6474 (2)	0.98483 (15)	0.0526 (7)
C32	0.4393 (3)	0.6817 (3)	1.07581 (18)	0.0729 (10)
C33	0.3872 (3)	0.6855 (3)	1.15265 (19)	0.0841 (10)
C34	0.2624 (3)	0.6584 (3)	1.1401 (2)	0.0803 (10)
C35	0.1891 (3)	0.6286 (3)	1.0519 (2)	0.0867 (11)
C36	0.2405 (3)	0.6232 (3)	0.97499 (19)	0.0749 (10)
C37	0.4113 (2)	0.5258 (2)	0.82567 (15)	0.0521 (7)
C38	0.3391 (2)	0.3971 (2)	0.79784 (15)	0.0528 (8)
C39	0.1917 (2)	0.2488 (2)	0.92415 (17)	0.0579 (8)
C40	0.2397 (3)	0.3436 (3)	1.03009 (18)	0.0736 (10)
C41	0.1395 (3)	0.3362 (3)	1.0833 (2)	0.0788 (10)
C42	0.0615 (3)	0.2083 (3)	1.0657 (2)	0.0745 (10)
C43	0.0033 (3)	0.1244 (3)	0.9559 (2)	0.0751 (10)
C44	0.1045 (3)	0.1235 (2)	0.9033 (2)	0.0770 (10)
C45	−0.0340 (3)	0.2019 (3)	1.1234 (2)	0.0901 (12)
C46	0.0227 (4)	0.2544 (4)	1.2315 (3)	0.1145 (16)
H2	0.11020	0.08990	0.49220	0.0860*
H1N	0.362 (2)	0.246 (2)	0.5898 (19)	0.062 (7)*
H5	0.28770	−0.10920	0.26000	0.0750*
H9	0.56410	−0.04090	0.40930	0.0850*
H10	0.69740	−0.09100	0.32000	0.1020*
H11	0.77020	0.00340	0.22990	0.1090*
H12	0.71090	0.15030	0.23000	0.1130*
H2N	0.693 (2)	0.237 (3)	0.534 (2)	0.072 (8)*
H3	−0.01470	−0.09200	0.35160	0.0890*
H17B	0.94590	0.21980	0.55600	0.1000*
H18A	1.04670	0.27370	0.45240	0.1270*
H18B	1.00290	0.37680	0.47230	0.1270*
H19	1.18950	0.38310	0.60100	0.1200*
H20A	1.11240	0.56930	0.64710	0.1200*
H20B	1.21860	0.56970	0.71610	0.1200*
H21A	1.07410	0.41830	0.73490	0.1080*
H21B	1.03000	0.52250	0.76020	0.1080*
H22A	1.22650	0.53750	0.51510	0.1310*	0.817 (6)
H22B	1.33040	0.55990	0.60040	0.1310*	0.817 (6)
H23A	1.36860	0.46880	0.45370	0.1900*	0.817 (6)
H23B	1.23510	0.35960	0.41340	0.1900*	0.817 (6)
H23C	1.33770	0.38050	0.49880	0.1900*	0.817 (6)
H13	0.57860	0.20270	0.32020	0.0860*
H17A	0.84800	0.23270	0.49020	0.1000*
H22C	1.23840	0.33610	0.48320	0.1310*	0.183 (6)
H22D	1.19020	0.41020	0.44620	0.1310*	0.183 (6)
H23D	1.39350	0.50710	0.48030	0.1900*	0.183 (6)
H23E	1.42060	0.49200	0.57380	0.1900*	0.183 (6)
H23F	1.36940	0.58660	0.57710	0.1900*	0.183 (6)
H4N	0.498 (2)	0.498 (2)	0.7245 (19)	0.065 (7)*
H5N	0.314 (2)	0.436 (2)	0.9156 (14)	0.051 (7)*
H25	0.64700	0.70880	0.71390	0.0860*
H26	0.71830	0.91740	0.79960	0.0990*
H28	0.52420	0.89380	0.99360	0.0870*
H32	0.52510	0.70250	1.08560	0.0870*
H33	0.43770	0.70670	1.21280	0.1010*
H34	0.22720	0.66000	1.19130	0.0960*
H35	0.10430	0.61190	1.04360	0.1040*
H36	0.18950	0.60290	0.91540	0.0900*
H40A	0.27480	0.42330	1.03430	0.0880*
H40B	0.30720	0.33500	1.06280	0.0880*
H41A	0.08380	0.36550	1.06210	0.0940*
H41B	0.17940	0.38920	1.15330	0.0940*
H42	0.12010	0.18130	1.08810	0.0890*
H43A	−0.04730	0.04260	0.94380	0.0900*
H43B	−0.05160	0.15130	0.93010	0.0900*
H44A	0.15310	0.08770	0.92370	0.0920*
H44B	0.06490	0.07330	0.83300	0.0920*
H45A	−0.08110	0.24500	1.11400	0.1080*
H45B	−0.09300	0.11760	1.09730	0.1080*
H46A	0.08040	0.33820	1.25830	0.1370*
H46B	0.06690	0.21030	1.24170	0.1370*
H46C	−0.04290	0.24820	1.26350	0.1370*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0663 (10)	0.0881 (12)	0.0889 (11)	0.0211 (9)	0.0103 (8)	0.0211 (9)
O1	0.0809 (13)	0.0725 (11)	0.0617 (10)	0.0379 (10)	0.0299 (9)	0.0169 (9)
N1	0.0721 (14)	0.0673 (13)	0.0537 (11)	0.0388 (12)	0.0331 (10)	0.0267 (10)
N2	0.0667 (14)	0.0652 (14)	0.0505 (11)	0.0296 (12)	0.0162 (10)	0.0125 (10)
N3	0.0718 (15)	0.0743 (14)	0.0499 (10)	0.0305 (12)	0.0137 (10)	0.0194 (10)
C1	0.0628 (15)	0.0659 (15)	0.0558 (12)	0.0330 (13)	0.0259 (11)	0.0323 (11)
C2	0.0692 (18)	0.092 (2)	0.0718 (16)	0.0448 (16)	0.0382 (14)	0.0425 (15)
C3	0.0604 (17)	0.089 (2)	0.0780 (17)	0.0322 (16)	0.0249 (14)	0.0426 (16)
C4	0.0621 (17)	0.0685 (16)	0.0665 (15)	0.0248 (14)	0.0164 (12)	0.0279 (13)
C5	0.0657 (16)	0.0654 (15)	0.0575 (13)	0.0318 (13)	0.0246 (11)	0.0264 (12)
C6	0.0584 (14)	0.0615 (14)	0.0534 (12)	0.0316 (12)	0.0239 (10)	0.0302 (11)
C7	0.0598 (14)	0.0562 (13)	0.0493 (11)	0.0292 (12)	0.0238 (10)	0.0271 (10)
C8	0.0539 (13)	0.0541 (13)	0.0461 (10)	0.0241 (11)	0.0194 (9)	0.0203 (9)
C9	0.089 (2)	0.0674 (16)	0.0799 (16)	0.0468 (16)	0.0427 (15)	0.0405 (14)
C10	0.091 (2)	0.0739 (19)	0.100 (2)	0.0515 (18)	0.0443 (18)	0.0340 (17)
C11	0.084 (2)	0.101 (2)	0.087 (2)	0.050 (2)	0.0496 (17)	0.0290 (18)
C12	0.099 (2)	0.128 (3)	0.093 (2)	0.059 (2)	0.0607 (19)	0.068 (2)
C13	0.0769 (18)	0.0859 (19)	0.0782 (16)	0.0440 (16)	0.0393 (14)	0.0506 (15)
C14	0.0636 (15)	0.0586 (13)	0.0517 (11)	0.0326 (12)	0.0276 (10)	0.0273 (10)
C15	0.0711 (16)	0.0626 (14)	0.0490 (11)	0.0346 (13)	0.0290 (11)	0.0277 (11)
C16	0.0723 (18)	0.0768 (17)	0.0557 (13)	0.0328 (15)	0.0174 (12)	0.0290 (12)
C17	0.079 (2)	0.089 (2)	0.0744 (17)	0.0402 (18)	0.0249 (15)	0.0286 (16)
C18	0.107 (3)	0.155 (4)	0.082 (2)	0.077 (3)	0.041 (2)	0.059 (2)
C19	0.080 (2)	0.133 (3)	0.129 (3)	0.049 (2)	0.037 (2)	0.094 (3)
C20	0.077 (2)	0.105 (3)	0.113 (3)	0.036 (2)	0.0085 (19)	0.053 (2)
C21	0.071 (2)	0.104 (2)	0.0746 (18)	0.0330 (18)	0.0043 (15)	0.0319 (17)
C22A	0.110 (4)	0.102 (4)	0.141 (4)	0.048 (3)	0.050 (3)	0.074 (4)
C23A	0.134 (5)	0.165 (6)	0.138 (5)	0.078 (5)	0.078 (4)	0.103 (4)
C23B	0.134 (5)	0.165 (6)	0.138 (5)	0.078 (5)	0.078 (4)	0.103 (4)
C22B	0.110 (4)	0.102 (4)	0.141 (4)	0.048 (3)	0.050 (3)	0.074 (4)
F2	0.1159 (17)	0.0648 (11)	0.170 (2)	0.0284 (12)	0.0460 (15)	0.0509 (12)
O2	0.0988 (14)	0.0617 (10)	0.0562 (9)	0.0350 (10)	0.0394 (9)	0.0219 (8)
N4	0.0674 (13)	0.0624 (13)	0.0530 (10)	0.0330 (11)	0.0272 (9)	0.0285 (10)
N5	0.0665 (13)	0.0514 (12)	0.0492 (10)	0.0246 (11)	0.0224 (9)	0.0203 (9)
N6	0.0610 (12)	0.0545 (11)	0.0594 (11)	0.0257 (10)	0.0260 (9)	0.0255 (9)
C24	0.0588 (14)	0.0657 (15)	0.0608 (13)	0.0304 (13)	0.0192 (11)	0.0352 (12)
C25	0.0691 (17)	0.087 (2)	0.0766 (16)	0.0347 (16)	0.0277 (13)	0.0516 (15)
C26	0.0702 (19)	0.081 (2)	0.107 (2)	0.0257 (17)	0.0264 (16)	0.0609 (18)
C27	0.0718 (19)	0.0621 (17)	0.113 (2)	0.0248 (15)	0.0224 (17)	0.0439 (17)
C28	0.0696 (17)	0.0651 (16)	0.0833 (17)	0.0340 (15)	0.0228 (14)	0.0316 (14)
C29	0.0574 (14)	0.0590 (14)	0.0613 (13)	0.0304 (12)	0.0184 (11)	0.0300 (11)
C30	0.0543 (13)	0.0567 (13)	0.0512 (11)	0.0288 (11)	0.0167 (10)	0.0244 (10)
C31	0.0575 (14)	0.0513 (12)	0.0472 (11)	0.0281 (11)	0.0171 (10)	0.0176 (9)
C32	0.0635 (17)	0.091 (2)	0.0556 (13)	0.0333 (15)	0.0156 (12)	0.0278 (13)
C33	0.096 (2)	0.099 (2)	0.0509 (13)	0.0426 (19)	0.0214 (14)	0.0296 (14)
C34	0.099 (2)	0.0750 (18)	0.0646 (16)	0.0385 (17)	0.0440 (16)	0.0260 (14)
C35	0.0663 (18)	0.108 (2)	0.0825 (19)	0.0433 (18)	0.0366 (15)	0.0345 (17)
C36	0.0630 (16)	0.101 (2)	0.0584 (14)	0.0444 (16)	0.0183 (12)	0.0284 (14)
C37	0.0587 (14)	0.0600 (13)	0.0476 (11)	0.0311 (12)	0.0219 (10)	0.0284 (10)
C38	0.0591 (14)	0.0622 (14)	0.0477 (11)	0.0351 (12)	0.0238 (10)	0.0261 (10)
C39	0.0583 (14)	0.0600 (14)	0.0642 (13)	0.0306 (12)	0.0244 (11)	0.0315 (11)
C40	0.0717 (18)	0.0780 (18)	0.0615 (14)	0.0174 (15)	0.0172 (13)	0.0375 (14)
C41	0.090 (2)	0.0697 (17)	0.0641 (15)	0.0232 (16)	0.0301 (14)	0.0285 (13)
C42	0.0787 (19)	0.0749 (18)	0.0763 (17)	0.0306 (15)	0.0328 (14)	0.0414 (14)
C43	0.0750 (19)	0.0592 (15)	0.0782 (17)	0.0153 (14)	0.0270 (14)	0.0317 (13)
C44	0.089 (2)	0.0598 (16)	0.0830 (18)	0.0299 (15)	0.0360 (15)	0.0340 (14)
C45	0.095 (2)	0.088 (2)	0.091 (2)	0.0340 (19)	0.0387 (18)	0.0478 (18)
C46	0.127 (3)	0.143 (3)	0.094 (2)	0.058 (3)	0.057 (2)	0.069 (2)

Geometric parameters (Å, º) top

F1—C4	1.364 (4)	C21—H21B	0.9700
F2—C27	1.364 (5)	C21—H21A	0.9700
O1—C15	1.218 (3)	C22A—H22B	0.9700
O2—C38	1.220 (3)	C22A—H22A	0.9700
N1—C1	1.370 (3)	C22B—H22D	0.9700
N1—C14	1.378 (4)	C22B—H22C	0.9700
N2—C15	1.344 (4)	C23A—H23A	0.9600
N2—N3	1.384 (3)	C23A—H23C	0.9600
N3—C16	1.280 (5)	C23A—H23B	0.9600
N1—H1N	0.85 (3)	C23B—H23E	0.9600
N2—H2N	0.81 (3)	C23B—H23D	0.9700
N4—C37	1.378 (3)	C23B—H23F	0.9600
N4—C24	1.362 (4)	C24—C29	1.405 (3)
N5—C38	1.349 (3)	C24—C25	1.403 (5)
N5—N6	1.377 (4)	C25—C26	1.367 (5)
N6—C39	1.280 (3)	C26—C27	1.380 (5)
N4—H4N	0.85 (3)	C27—C28	1.368 (6)
N5—H5N	0.77 (2)	C28—C29	1.402 (5)
C1—C2	1.399 (5)	C29—C30	1.433 (4)
C1—C6	1.407 (3)	C30—C37	1.384 (3)
C2—C3	1.368 (5)	C30—C31	1.488 (3)
C3—C4	1.394 (5)	C31—C36	1.375 (5)
C4—C5	1.358 (5)	C31—C32	1.385 (4)
C5—C6	1.400 (3)	C32—C33	1.389 (4)
C6—C7	1.431 (4)	C33—C34	1.362 (5)
C7—C14	1.383 (3)	C34—C35	1.367 (4)
C7—C8	1.483 (3)	C35—C36	1.382 (5)
C8—C13	1.386 (4)	C37—C38	1.472 (4)
C8—C9	1.384 (4)	C39—C40	1.497 (4)
C9—C10	1.374 (5)	C39—C44	1.502 (4)
C10—C11	1.359 (5)	C40—C41	1.509 (5)
C11—C12	1.377 (6)	C41—C42	1.522 (6)
C12—C13	1.375 (5)	C42—C43	1.518 (4)
C14—C15	1.475 (3)	C42—C45	1.511 (5)
C16—C21	1.498 (5)	C43—C44	1.515 (5)
C16—C17	1.489 (4)	C45—C46	1.500 (5)
C17—C18	1.537 (6)	C25—H25	0.9300
C18—C19	1.491 (6)	C26—H26	0.9300
C19—C22A	1.545 (8)	C28—H28	0.9300
C19—C20	1.493 (6)	C32—H32	0.9300
C19—C22B	1.55 (2)	C33—H33	0.9300
C20—C21	1.503 (6)	C34—H34	0.9300
C22A—C23A	1.472 (10)	C35—H35	0.9300
C22B—C23B	1.48 (3)	C36—H36	0.9300
C2—H2	0.9300	C40—H40A	0.9700
C3—H3	0.9300	C40—H40B	0.9700
C5—H5	0.9300	C41—H41A	0.9700
C9—H9	0.9300	C41—H41B	0.9700
C10—H10	0.9300	C42—H42	0.9800
C11—H11	0.9300	C43—H43A	0.9700
C12—H12	0.9300	C43—H43B	0.9700
C13—H13	0.9300	C44—H44A	0.9700
C17—H17B	0.9700	C44—H44B	0.9700
C17—H17A	0.9700	C45—H45A	0.9700
C18—H18A	0.9700	C45—H45B	0.9700
C18—H18B	0.9700	C46—H46A	0.9600
C19—H19	0.9800	C46—H46B	0.9600
C20—H20B	0.9700	C46—H46C	0.9600
C20—H20A	0.9700

C1—N1—C14	109.5 (2)	H22C—C22B—H22D	107.00
N3—N2—C15	120.6 (2)	C23B—C22B—H22C	108.00
N2—N3—C16	116.5 (2)	H23B—C23A—H23C	110.00
C14—N1—H1N	125.6 (18)	C22A—C23A—H23B	109.00
C1—N1—H1N	123.8 (18)	H23A—C23A—H23B	109.00
N3—N2—H2N	128 (2)	H23A—C23A—H23C	109.00
C15—N2—H2N	112 (2)	C22A—C23A—H23C	110.00
C24—N4—C37	109.2 (2)	C22A—C23A—H23A	109.00
N6—N5—C38	121.6 (2)	C22B—C23B—H23F	110.00
N5—N6—C39	116.6 (2)	C22B—C23B—H23E	110.00
C37—N4—H4N	120 (2)	H23D—C23B—H23F	109.00
C24—N4—H4N	129.1 (19)	H23E—C23B—H23F	110.00
C38—N5—H5N	110.6 (19)	H23D—C23B—H23E	109.00
N6—N5—H5N	127.1 (19)	C22B—C23B—H23D	109.00
N1—C1—C6	107.5 (2)	N4—C24—C25	130.3 (2)
N1—C1—C2	130.8 (2)	N4—C24—C29	108.2 (2)
C2—C1—C6	121.7 (2)	C25—C24—C29	121.6 (3)
C1—C2—C3	117.8 (3)	C24—C25—C26	117.5 (3)
C2—C3—C4	119.8 (3)	C25—C26—C27	120.5 (4)
F1—C4—C3	117.4 (3)	F2—C27—C28	118.8 (3)
C3—C4—C5	123.9 (3)	C26—C27—C28	123.9 (4)
F1—C4—C5	118.7 (3)	F2—C27—C26	117.3 (4)
C4—C5—C6	117.2 (2)	C27—C28—C29	116.7 (3)
C1—C6—C5	119.5 (2)	C28—C29—C30	133.1 (2)
C5—C6—C7	132.9 (2)	C24—C29—C28	119.8 (3)
C1—C6—C7	107.6 (2)	C24—C29—C30	107.1 (2)
C8—C7—C14	129.5 (2)	C31—C30—C37	127.6 (2)
C6—C7—C14	106.3 (2)	C29—C30—C37	106.3 (2)
C6—C7—C8	124.2 (2)	C29—C30—C31	126.1 (2)
C7—C8—C9	121.4 (2)	C30—C31—C36	123.0 (2)
C7—C8—C13	120.6 (3)	C32—C31—C36	117.6 (3)
C9—C8—C13	117.9 (3)	C30—C31—C32	119.4 (2)
C8—C9—C10	121.4 (3)	C31—C32—C33	121.0 (3)
C9—C10—C11	119.9 (4)	C32—C33—C34	120.1 (3)
C10—C11—C12	119.9 (3)	C33—C34—C35	119.7 (3)
C11—C12—C13	120.4 (4)	C34—C35—C36	120.3 (3)
C8—C13—C12	120.4 (4)	C31—C36—C35	121.3 (3)
N1—C14—C15	117.9 (2)	N4—C37—C30	109.3 (2)
N1—C14—C7	109.2 (2)	N4—C37—C38	117.9 (2)
C7—C14—C15	132.8 (2)	C30—C37—C38	132.8 (2)
O1—C15—C14	121.7 (2)	N5—C38—C37	115.6 (2)
N2—C15—C14	114.3 (2)	O2—C38—N5	122.5 (3)
O1—C15—N2	124.0 (2)	O2—C38—C37	122.0 (2)
N3—C16—C17	128.9 (3)	N6—C39—C44	116.5 (2)
C17—C16—C21	114.7 (3)	C40—C39—C44	115.4 (2)
N3—C16—C21	116.4 (3)	N6—C39—C40	128.1 (3)
C16—C17—C18	110.0 (3)	C39—C40—C41	113.3 (3)
C17—C18—C19	116.1 (3)	C40—C41—C42	113.4 (3)
C18—C19—C22A	117.0 (4)	C41—C42—C43	108.8 (3)
C18—C19—C22B	95.2 (8)	C41—C42—C45	113.4 (3)
C18—C19—C20	111.0 (4)	C43—C42—C45	113.1 (3)
C20—C19—C22A	108.7 (4)	C42—C43—C44	110.8 (3)
C20—C19—C22B	144.0 (10)	C39—C44—C43	112.3 (3)
C19—C20—C21	113.2 (4)	C42—C45—C46	114.0 (3)
C16—C21—C20	111.3 (3)	C24—C25—H25	121.00
C19—C22A—C23A	114.0 (6)	C26—C25—H25	121.00
C19—C22B—C23B	117.7 (17)	C25—C26—H26	120.00
C1—C2—H2	121.00	C27—C26—H26	120.00
C3—C2—H2	121.00	C27—C28—H28	122.00
C2—C3—H3	120.00	C29—C28—H28	122.00
C4—C3—H3	120.00	C31—C32—H32	119.00
C6—C5—H5	121.00	C33—C32—H32	119.00
C4—C5—H5	121.00	C32—C33—H33	120.00
C10—C9—H9	119.00	C34—C33—H33	120.00
C8—C9—H9	119.00	C33—C34—H34	120.00
C9—C10—H10	120.00	C35—C34—H34	120.00
C11—C10—H10	120.00	C34—C35—H35	120.00
C10—C11—H11	120.00	C36—C35—H35	120.00
C12—C11—H11	120.00	C31—C36—H36	119.00
C13—C12—H12	120.00	C35—C36—H36	119.00
C11—C12—H12	120.00	C39—C40—H40A	109.00
C12—C13—H13	120.00	C39—C40—H40B	109.00
C8—C13—H13	120.00	C41—C40—H40A	109.00
C18—C17—H17B	110.00	C41—C40—H40B	109.00
C16—C17—H17A	110.00	H40A—C40—H40B	108.00
C16—C17—H17B	110.00	C40—C41—H41A	109.00
C18—C17—H17A	110.00	C40—C41—H41B	109.00
H17A—C17—H17B	108.00	C42—C41—H41A	109.00
C17—C18—H18A	108.00	C42—C41—H41B	109.00
C17—C18—H18B	108.00	H41A—C41—H41B	108.00
C19—C18—H18A	108.00	C41—C42—H42	107.00
C19—C18—H18B	108.00	C43—C42—H42	107.00
H18A—C18—H18B	107.00	C45—C42—H42	107.00
C18—C19—H19	106.00	C42—C43—H43A	110.00
C22B—C19—H19	88.00	C42—C43—H43B	110.00
C20—C19—H19	107.00	C44—C43—H43A	109.00
C22A—C19—H19	107.00	C44—C43—H43B	109.00
H20A—C20—H20B	108.00	H43A—C43—H43B	108.00
C19—C20—H20A	109.00	C39—C44—H44A	109.00
C21—C20—H20B	109.00	C39—C44—H44B	109.00
C19—C20—H20B	109.00	C43—C44—H44A	109.00
C21—C20—H20A	109.00	C43—C44—H44B	109.00
H21A—C21—H21B	108.00	H44A—C44—H44B	108.00
C16—C21—H21B	109.00	C42—C45—H45A	109.00
C20—C21—H21A	109.00	C42—C45—H45B	109.00
C20—C21—H21B	109.00	C46—C45—H45A	109.00
C16—C21—H21A	109.00	C46—C45—H45B	109.00
C19—C22A—H22A	109.00	H45A—C45—H45B	108.00
C19—C22A—H22B	109.00	C45—C46—H46A	109.00
H22A—C22A—H22B	108.00	C45—C46—H46B	109.00
C23A—C22A—H22B	109.00	C45—C46—H46C	109.00
C23A—C22A—H22A	109.00	H46A—C46—H46B	109.00
C19—C22B—H22C	108.00	H46A—C46—H46C	110.00
C19—C22B—H22D	108.00	H46B—C46—H46C	110.00
C23B—C22B—H22D	108.00

C1—N1—C14—C15	−176.4 (2)	N3—C16—C21—C20	−126.5 (4)
C14—N1—C1—C2	179.8 (3)	C16—C17—C18—C19	47.8 (5)
C14—N1—C1—C6	−0.9 (3)	C17—C18—C19—C22A	−175.1 (4)
C1—N1—C14—C7	1.3 (3)	C17—C18—C19—C20	−49.5 (6)
C15—N2—N3—C16	−175.1 (3)	C22A—C19—C20—C21	−178.0 (4)
N3—N2—C15—O1	2.9 (4)	C18—C19—C20—C21	51.9 (5)
N3—N2—C15—C14	−175.6 (2)	C18—C19—C22A—C23A	−65.3 (7)
N2—N3—C16—C21	−177.0 (3)	C20—C19—C22A—C23A	168.0 (5)
N2—N3—C16—C17	3.0 (5)	C19—C20—C21—C16	−54.1 (5)
C37—N4—C24—C29	−1.0 (3)	C25—C24—C29—C30	−178.4 (3)
C24—N4—C37—C38	178.8 (2)	N4—C24—C25—C26	179.1 (3)
C37—N4—C24—C25	178.4 (3)	C29—C24—C25—C26	−1.5 (5)
C24—N4—C37—C30	0.6 (3)	N4—C24—C29—C30	1.1 (3)
C38—N5—N6—C39	175.5 (3)	C25—C24—C29—C28	1.7 (4)
N6—N5—C38—O2	−6.1 (4)	N4—C24—C29—C28	−178.8 (3)
N6—N5—C38—C37	174.1 (2)	C24—C25—C26—C27	0.7 (5)
N5—N6—C39—C44	178.9 (2)	C25—C26—C27—F2	−178.8 (3)
N5—N6—C39—C40	−3.8 (4)	C25—C26—C27—C28	−0.1 (6)
N1—C1—C2—C3	−179.6 (3)	C26—C27—C28—C29	0.3 (6)
N1—C1—C6—C7	0.2 (3)	F2—C27—C28—C29	179.0 (3)
C6—C1—C2—C3	1.2 (5)	C27—C28—C29—C30	179.1 (3)
C2—C1—C6—C5	−1.1 (4)	C27—C28—C29—C24	−1.0 (4)
N1—C1—C6—C5	179.6 (2)	C28—C29—C30—C31	−3.0 (5)
C2—C1—C6—C7	179.6 (3)	C24—C29—C30—C37	−0.8 (3)
C1—C2—C3—C4	0.2 (5)	C28—C29—C30—C37	179.1 (3)
C2—C3—C4—F1	177.5 (3)	C24—C29—C30—C31	177.1 (2)
C2—C3—C4—C5	−1.9 (6)	C29—C30—C37—N4	0.1 (3)
C3—C4—C5—C6	2.0 (5)	C29—C30—C31—C32	−77.2 (4)
F1—C4—C5—C6	−177.4 (3)	C29—C30—C37—C38	−177.7 (3)
C4—C5—C6—C1	−0.5 (4)	C31—C30—C37—N4	−177.7 (2)
C4—C5—C6—C7	178.6 (3)	C37—C30—C31—C36	−76.8 (4)
C5—C6—C7—C14	−178.7 (3)	C37—C30—C31—C32	100.2 (3)
C5—C6—C7—C8	2.9 (5)	C31—C30—C37—C38	4.5 (4)
C1—C6—C7—C14	0.5 (3)	C29—C30—C31—C36	105.7 (3)
C1—C6—C7—C8	−177.9 (2)	C32—C31—C36—C35	−2.3 (5)
C8—C7—C14—N1	177.3 (3)	C30—C31—C36—C35	174.9 (3)
C6—C7—C8—C9	−78.4 (3)	C30—C31—C32—C33	−174.1 (3)
C6—C7—C14—N1	−1.1 (3)	C36—C31—C32—C33	3.1 (5)
C14—C7—C8—C13	−79.2 (4)	C31—C32—C33—C34	−1.8 (6)
C6—C7—C14—C15	176.2 (3)	C32—C33—C34—C35	−0.6 (6)
C6—C7—C8—C13	98.9 (3)	C33—C34—C35—C36	1.5 (6)
C14—C7—C8—C9	103.5 (4)	C34—C35—C36—C31	0.0 (6)
C8—C7—C14—C15	−5.5 (5)	N4—C37—C38—N5	164.4 (2)
C13—C8—C9—C10	−0.5 (4)	C30—C37—C38—O2	162.2 (3)
C9—C8—C13—C12	0.8 (4)	C30—C37—C38—N5	−17.9 (4)
C7—C8—C13—C12	−176.6 (3)	N4—C37—C38—O2	−15.5 (4)
C7—C8—C9—C10	176.8 (3)	N6—C39—C40—C41	139.8 (3)
C8—C9—C10—C11	−0.1 (5)	C44—C39—C40—C41	−42.9 (4)
C9—C10—C11—C12	0.4 (5)	N6—C39—C44—C43	−135.5 (3)
C10—C11—C12—C13	−0.1 (5)	C40—C39—C44—C43	46.9 (4)
C11—C12—C13—C8	−0.6 (5)	C39—C40—C41—C42	48.0 (4)
C7—C14—C15—O1	168.5 (3)	C40—C41—C42—C43	−56.4 (4)
C7—C14—C15—N2	−13.1 (4)	C40—C41—C42—C45	176.8 (3)
N1—C14—C15—N2	164.0 (2)	C41—C42—C43—C44	59.6 (4)
N1—C14—C15—O1	−14.5 (4)	C45—C42—C43—C44	−173.4 (3)
C21—C16—C17—C18	−49.2 (4)	C41—C42—C45—C46	−72.2 (4)
N3—C16—C17—C18	130.9 (4)	C43—C42—C45—C46	163.3 (4)
C17—C16—C21—C20	53.6 (5)	C42—C43—C44—C39	−55.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.85 (3)	2.00 (3)	2.836 (3)	168 (3)
N4—H4N···O1	0.85 (3)	2.08 (3)	2.887 (3)	160 (2)
C17—H17A···N2	0.97	2.46	2.834 (5)	102
C40—H40A···N5	0.97	2.45	2.822 (4)	102
C9—H9···Cg1ⁱ	0.93	2.81	3.636 (3)	149
C17—H17A···Cg3	0.97	2.87	3.820 (3)	165
C40—H40A···Cg7	0.97	2.79	3.727 (4)	163
C40—H40B···Cg5ⁱⁱ	0.97	2.65	3.595 (4)	163

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.85 (3)	2.00 (3)	2.836 (3)	168 (3)
N4—H4N···O1	0.85 (3)	2.08 (3)	2.887 (3)	160 (2)
C9—H9···Cg1ⁱ	0.93	2.81	3.636 (3)	149
C17—H17A···Cg3	0.97	2.87	3.820 (3)	165
C40—H40A···Cg7	0.97	2.79	3.727 (4)	163
C40—H40B···Cg5ⁱⁱ	0.97	2.65	3.595 (4)	163

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Scientific Research Projects Coordination Unit of İstanbul University (project No. T-471/25062004).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Çelikesir, S. T., Akkurt, M., Üstündağ, G. C. & Büyükgüngör, O. (2013a). Acta Cryst. E69, o1202. CSD CrossRef IUCr Journals Google Scholar
Çelikesir, S. T., Akkurt, M., Üstündağ, G. C., Çapan, G. & Büyükgüngör, O. (2013b). Acta Cryst. E69, o1211–o1212. CSD CrossRef IUCr Journals Google Scholar
Cihan-Üstündağ, G. & Çapan, G. (2012). Mol. Divers. 16, 525–539. Web of Science PubMed Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Göktas, F., Vanderlinden, E., Naesens, L., Cesur, N. & Cesur, Z. (2012). Bioorg. Med. Chem. 20, 7155–7159. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1331

doi:10.1107/S1600536813020394

Open

access