1-[2-(Benzyl-amino)-4-pyrid-yl]-2-(4-fluoro-phen-yl)ethane-1,2-dione.

The crystal structure of the title compound, C(20)H(15)FN(2)O(2), contains two crystallographically independent mol-ecules, which are related by a pseudo-inversion center and linked into dimers via inter-molecular N-H⋯N hydrogen bonds. The 4-fluoro-phenyl ring of mol-ecule A makes dihedral angles of 17.17 (16) and 62.25 (15)°, respectively, with the phenyl and pyridine rings. The 4-fluoro-phenyl ring of mol-ecule B makes dihedral angles of 8.50 (16) and 64.59 (15)°, respectively, with the phenyl and pyridine rings. The dihedral angle between the pyridine ring and the phenyl ring of mol-ecule A [60.97 (15)°] is bigger than in mol-ecule B [59.49 (15)°]. The dihedral angle between the two pyridine rings is 1.37 (14)° and between the two phenyl rings is 3.64 (16)°.

Related literature

For α-diketones as inter­mediates in the synthesis of heterocycles, see: Ohta et al. (1982 ▶); Wolkenberg et al. (2004 ▶); Zhao et al. (2003 ▶,2004 ▶).

Experimental

Crystal data

C20H15FN2O2

M = 334.34

Orthorhombic,

a = 12.0951 (13) Å

b = 7.4097 (8) Å

c = 35.163 (5) Å

V = 3151.3 (7) Å3

Z = 8

Cu Kα radiation

μ = 0.83 mm−1

T = 193 K

0.38 × 0.19 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

5637 measured reflections

5558 independent reflections

4832 reflections with I > 2σ(I)

R int = 0.054

3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.05

5558 reflections

451 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 2522 Friedel pairs

Flack parameter: 0.35 (19)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019801/nc2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019801/nc2145Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H15FN2O2	F(000) = 1392
Mr = 334.34	Dx = 1.409 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 12.0951 (13) Å	θ = 30–46°
b = 7.4097 (8) Å	µ = 0.83 mm−1
c = 35.163 (5) Å	T = 193 K
V = 3151.3 (7) Å3	Plate, light brown
Z = 8	0.38 × 0.19 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.054
Radiation source: FR571 rotating anode	θmax = 70.0°, θmin = 2.5°
graphite	h = −14→14
ω/2θ scans	k = −9→9
5637 measured reflections	l = −42→42
5558 independent reflections	3 standard reflections every 60 min
4832 reflections with I > 2σ(I)	intensity decay: 2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.079P)2 + 0.0063P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
5558 reflections	Δρmax = 0.19 e Å−3
451 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 2522 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.35 (19)

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.

	x	y	z	Uiso*/Ueq
F1	0.35951 (18)	0.4513 (3)	0.22618 (6)	0.0511 (6)
C1	0.5181 (2)	0.3936 (4)	0.32829 (8)	0.0219 (6)
C2	0.5644 (3)	0.3233 (4)	0.29506 (8)	0.0261 (6)
H2	0.6328	0.2605	0.2963	0.031*
C3	0.5120 (3)	0.3438 (5)	0.26040 (9)	0.0321 (8)
H3	0.5437	0.2974	0.2377	0.038*
C4	0.4121 (3)	0.4340 (5)	0.25979 (8)	0.0315 (7)
C5	0.3636 (3)	0.5030 (5)	0.29206 (9)	0.0308 (7)
H5	0.2946	0.5640	0.2906	0.037*
C6	0.4166 (2)	0.4825 (4)	0.32648 (8)	0.0253 (6)
H6	0.3839	0.5289	0.3490	0.030*
C7	0.5813 (2)	0.3725 (4)	0.36420 (8)	0.0233 (6)
O8	0.67739 (19)	0.3251 (3)	0.36487 (6)	0.0356 (6)
C9	0.5196 (3)	0.3942 (4)	0.40219 (8)	0.0240 (6)
O10	0.42846 (19)	0.3260 (3)	0.40449 (6)	0.0356 (6)
C11	0.5752 (3)	0.4838 (4)	0.43500 (8)	0.0221 (6)
C12	0.6723 (2)	0.5836 (4)	0.43184 (8)	0.0229 (6)
H12	0.7112	0.5924	0.4084	0.027*
C13	0.7097 (2)	0.6697 (4)	0.46454 (8)	0.0241 (6)
H13	0.7738	0.7430	0.4624	0.029*
N14	0.6625 (2)	0.6572 (3)	0.49862 (7)	0.0230 (5)
C15	0.5701 (2)	0.5550 (4)	0.50181 (8)	0.0223 (6)
C16	0.5233 (3)	0.4685 (4)	0.47028 (8)	0.0239 (6)
H16	0.4572	0.4003	0.4729	0.029*
N17	0.5271 (2)	0.5395 (4)	0.53755 (6)	0.0249 (6)
H17	0.5433	0.6356	0.5543	0.030*
C18	0.4209 (3)	0.4514 (4)	0.54384 (8)	0.0253 (6)
H18A	0.4219	0.3300	0.5321	0.030*
H18B	0.3616	0.5226	0.5316	0.030*
C19	0.3972 (2)	0.4342 (4)	0.58592 (8)	0.0235 (6)
C20	0.4743 (3)	0.3576 (5)	0.61064 (9)	0.0301 (7)
H20	0.5423	0.3131	0.6008	0.036*
C21	0.4531 (3)	0.3457 (5)	0.64931 (9)	0.0335 (7)
H21	0.5065	0.2950	0.6660	0.040*
C22	0.3528 (3)	0.4088 (5)	0.66351 (8)	0.0318 (7)
H22	0.3377	0.4022	0.6900	0.038*
C23	0.2759 (3)	0.4803 (5)	0.63923 (9)	0.0325 (8)
H23	0.2074	0.5225	0.6490	0.039*
C24	0.2967 (3)	0.4919 (4)	0.60057 (9)	0.0261 (6)
H24	0.2420	0.5396	0.5840	0.031*
F2	0.88809 (18)	0.7836 (3)	0.85731 (5)	0.0467 (5)
C31	0.7257 (3)	0.9818 (4)	0.76425 (7)	0.0233 (6)
C32	0.6788 (3)	0.9983 (5)	0.80060 (8)	0.0287 (7)
H32	0.6093	1.0562	0.8036	0.034*
C33	0.7337 (3)	0.9305 (5)	0.83209 (8)	0.0332 (7)
H33	0.7032	0.9422	0.8569	0.040*
C34	0.8330 (3)	0.8461 (4)	0.82649 (9)	0.0313 (7)
C35	0.8795 (3)	0.8194 (4)	0.79135 (9)	0.0290 (7)
H35	0.9466	0.7542	0.7886	0.035*
C36	0.8256 (2)	0.8907 (4)	0.75999 (8)	0.0241 (6)
H36	0.8570	0.8772	0.7354	0.029*
C37	0.6681 (2)	1.0626 (4)	0.73148 (8)	0.0241 (6)
O38	0.57767 (19)	1.1330 (4)	0.73326 (6)	0.0361 (6)
C39	0.7292 (2)	1.0728 (4)	0.69328 (8)	0.0222 (6)
O40	0.81709 (18)	1.1522 (3)	0.69255 (6)	0.0307 (5)
C41	0.6762 (3)	0.9946 (4)	0.65860 (8)	0.0213 (6)
C42	0.5787 (2)	0.8949 (4)	0.66072 (8)	0.0238 (6)
H42	0.5397	0.8820	0.6840	0.029*
C43	0.5413 (3)	0.8159 (4)	0.62775 (9)	0.0246 (6)
H43	0.4759	0.7452	0.6291	0.030*
N44	0.5911 (2)	0.8321 (3)	0.59388 (6)	0.0228 (5)
C45	0.6849 (2)	0.9320 (4)	0.59180 (8)	0.0208 (6)
C46	0.7304 (2)	1.0139 (4)	0.62435 (8)	0.0220 (6)
H46	0.7971	1.0812	0.6227	0.026*
N47	0.7298 (2)	0.9502 (4)	0.55656 (7)	0.0251 (6)
H47	0.7030	0.8676	0.5383	0.030*
C48	0.8360 (3)	1.0397 (4)	0.55111 (8)	0.0261 (7)
H48A	0.8950	0.9675	0.5634	0.031*
H48B	0.8343	1.1597	0.5635	0.031*
C49	0.8623 (3)	1.0622 (4)	0.50941 (8)	0.0239 (6)
C50	0.7872 (3)	1.1396 (4)	0.48458 (9)	0.0287 (7)
H50	0.7173	1.1786	0.4938	0.034*
C51	0.8132 (3)	1.1606 (5)	0.44644 (9)	0.0328 (8)
H51	0.7608	1.2127	0.4296	0.039*
C52	0.9152 (3)	1.1059 (5)	0.43283 (8)	0.0328 (7)
H52	0.9327	1.1203	0.4067	0.039*
C53	0.9910 (3)	1.0306 (5)	0.45723 (9)	0.0321 (7)
H53	1.0611	0.9932	0.4480	0.038*
C54	0.9651 (3)	1.0090 (4)	0.49550 (9)	0.0261 (6)
H54	1.0179	0.9576	0.5123	0.031*

	U11	U22	U33	U12	U13	U23
F1	0.0571 (13)	0.0679 (15)	0.0282 (10)	−0.0039 (12)	−0.0212 (9)	0.0025 (10)
C1	0.0243 (14)	0.0239 (14)	0.0174 (13)	−0.0046 (12)	−0.0001 (11)	−0.0020 (11)
C2	0.0266 (15)	0.0285 (17)	0.0231 (14)	−0.0008 (13)	−0.0003 (12)	−0.0061 (12)
C3	0.0363 (17)	0.040 (2)	0.0198 (14)	−0.0057 (16)	0.0019 (12)	−0.0097 (13)
C4	0.0331 (17)	0.0404 (19)	0.0209 (14)	−0.0056 (16)	−0.0086 (12)	0.0032 (13)
C5	0.0251 (15)	0.0329 (16)	0.0344 (16)	0.0012 (15)	−0.0044 (13)	0.0034 (14)
C6	0.0269 (15)	0.0262 (15)	0.0228 (13)	0.0013 (13)	0.0029 (12)	−0.0015 (12)
C7	0.0258 (15)	0.0239 (14)	0.0202 (13)	0.0004 (13)	−0.0016 (12)	−0.0010 (11)
O8	0.0295 (12)	0.0499 (15)	0.0274 (11)	0.0116 (11)	−0.0028 (9)	−0.0086 (10)
C9	0.0271 (16)	0.0270 (16)	0.0180 (13)	−0.0007 (13)	0.0000 (11)	0.0017 (12)
O10	0.0352 (12)	0.0522 (15)	0.0196 (10)	−0.0137 (12)	−0.0018 (9)	−0.0015 (10)
C11	0.0261 (15)	0.0224 (14)	0.0179 (13)	0.0045 (13)	−0.0004 (12)	−0.0005 (11)
C12	0.0247 (14)	0.0268 (15)	0.0171 (12)	0.0031 (13)	−0.0002 (11)	0.0013 (11)
C13	0.0200 (14)	0.0240 (15)	0.0283 (15)	0.0005 (13)	0.0003 (11)	0.0024 (11)
N14	0.0232 (12)	0.0268 (13)	0.0189 (11)	−0.0033 (11)	−0.0013 (10)	−0.0017 (10)
C15	0.0226 (14)	0.0247 (15)	0.0196 (13)	0.0042 (13)	−0.0017 (11)	0.0011 (11)
C16	0.0273 (16)	0.0257 (15)	0.0188 (14)	−0.0023 (14)	−0.0014 (12)	0.0009 (11)
N17	0.0278 (14)	0.0298 (14)	0.0170 (11)	−0.0101 (12)	0.0006 (10)	−0.0039 (10)
C18	0.0254 (15)	0.0288 (15)	0.0218 (14)	−0.0084 (14)	−0.0013 (12)	−0.0034 (12)
C19	0.0268 (15)	0.0214 (14)	0.0222 (14)	−0.0076 (13)	−0.0016 (11)	−0.0018 (11)
C20	0.0310 (16)	0.0294 (17)	0.0298 (16)	0.0001 (15)	0.0028 (13)	−0.0002 (13)
C21	0.0391 (19)	0.0320 (18)	0.0295 (17)	0.0012 (16)	−0.0033 (14)	0.0057 (13)
C22	0.0425 (19)	0.0313 (18)	0.0216 (15)	−0.0010 (16)	0.0073 (13)	0.0006 (12)
C23	0.0307 (18)	0.0341 (18)	0.0327 (16)	−0.0034 (15)	0.0110 (14)	−0.0031 (14)
C24	0.0232 (15)	0.0265 (15)	0.0286 (15)	−0.0029 (14)	−0.0010 (13)	0.0008 (12)
F2	0.0580 (13)	0.0545 (13)	0.0275 (10)	0.0088 (11)	−0.0058 (9)	0.0144 (9)
C31	0.0265 (15)	0.0262 (15)	0.0173 (13)	−0.0051 (13)	0.0002 (11)	−0.0043 (11)
C32	0.0285 (16)	0.0333 (17)	0.0244 (15)	0.0011 (14)	0.0055 (12)	−0.0046 (13)
C33	0.046 (2)	0.0357 (17)	0.0182 (14)	−0.0005 (16)	0.0047 (13)	0.0008 (13)
C34	0.0433 (18)	0.0268 (16)	0.0238 (14)	−0.0042 (15)	−0.0058 (14)	0.0071 (12)
C35	0.0258 (16)	0.0318 (17)	0.0293 (15)	0.0012 (14)	0.0018 (12)	0.0024 (13)
C36	0.0264 (15)	0.0261 (15)	0.0199 (13)	−0.0029 (13)	0.0025 (11)	−0.0016 (11)
C37	0.0275 (15)	0.0261 (15)	0.0186 (13)	−0.0010 (14)	0.0008 (11)	−0.0060 (11)
O38	0.0307 (12)	0.0518 (15)	0.0257 (11)	0.0097 (12)	−0.0008 (9)	−0.0047 (10)
C39	0.0233 (14)	0.0258 (15)	0.0175 (13)	0.0015 (13)	0.0008 (11)	0.0016 (11)
O40	0.0295 (11)	0.0392 (13)	0.0234 (10)	−0.0109 (10)	−0.0032 (8)	0.0005 (9)
C41	0.0221 (14)	0.0238 (14)	0.0180 (13)	0.0022 (12)	−0.0018 (11)	0.0010 (11)
C42	0.0235 (14)	0.0269 (15)	0.0210 (13)	−0.0013 (13)	0.0036 (11)	−0.0012 (11)
C43	0.0218 (14)	0.0259 (15)	0.0263 (14)	−0.0019 (13)	−0.0017 (11)	0.0000 (12)
N44	0.0232 (12)	0.0258 (13)	0.0192 (11)	−0.0002 (11)	−0.0003 (9)	−0.0030 (9)
C45	0.0238 (14)	0.0195 (13)	0.0190 (13)	−0.0019 (13)	−0.0027 (11)	0.0012 (11)
C46	0.0214 (15)	0.0252 (15)	0.0195 (13)	−0.0010 (12)	0.0002 (12)	−0.0012 (11)
N47	0.0298 (14)	0.0300 (13)	0.0155 (10)	−0.0111 (12)	0.0012 (10)	−0.0016 (10)
C48	0.0286 (16)	0.0283 (16)	0.0213 (15)	−0.0082 (14)	0.0004 (12)	−0.0038 (12)
C49	0.0282 (16)	0.0200 (14)	0.0235 (14)	−0.0055 (14)	0.0024 (11)	−0.0023 (11)
C50	0.0284 (16)	0.0294 (16)	0.0284 (15)	0.0006 (14)	0.0014 (12)	0.0018 (12)
C51	0.0393 (19)	0.0317 (18)	0.0275 (15)	−0.0003 (16)	−0.0068 (14)	0.0050 (13)
C52	0.0486 (19)	0.0331 (17)	0.0167 (13)	−0.0072 (17)	0.0071 (13)	−0.0014 (13)
C53	0.0294 (16)	0.0363 (18)	0.0304 (15)	−0.0082 (15)	0.0061 (13)	−0.0051 (14)
C54	0.0249 (15)	0.0273 (15)	0.0259 (14)	−0.0041 (13)	0.0008 (13)	0.0016 (12)

F1—C4	1.349 (3)	C43—N44	1.340 (4)
C1—C6	1.395 (4)	N44—C45	1.357 (4)
C1—C2	1.396 (4)	C45—N47	1.360 (4)
C1—C7	1.484 (4)	C45—C46	1.408 (4)
C2—C3	1.382 (4)	N47—C48	1.458 (4)
C3—C4	1.381 (5)	C48—C49	1.510 (4)
C4—C5	1.376 (5)	C49—C50	1.384 (4)
C5—C6	1.378 (4)	C49—C54	1.392 (4)
C7—O8	1.214 (4)	C50—C51	1.386 (4)
C7—C9	1.539 (4)	C51—C52	1.383 (5)
C9—O10	1.215 (4)	C52—C53	1.374 (5)
C9—C11	1.491 (4)	C53—C54	1.391 (4)
C11—C12	1.392 (4)	N17—H17	0.9400
C11—C16	1.395 (4)	N47—H47	0.9400
C12—C13	1.391 (4)	C2—H2	0.9500
C13—N14	1.330 (4)	C3—H3	0.9500
N14—C15	1.355 (4)	C5—H5	0.9500
C15—N17	1.365 (4)	C6—H6	0.9500
C15—C16	1.400 (4)	C12—H12	0.9500
N17—C18	1.458 (4)	C13—H13	0.9500
C18—C19	1.513 (4)	C16—H16	0.9500
C19—C24	1.387 (4)	C18—H18B	0.9900
C19—C20	1.396 (4)	C18—H18A	0.9900
C20—C21	1.387 (4)	C20—H20	0.9500
C21—C22	1.393 (5)	C21—H21	0.9500
C22—C23	1.369 (5)	C22—H22	0.9500
C23—C24	1.385 (4)	C23—H23	0.9500
F2—C34	1.354 (3)	C24—H24	0.9500
C31—C36	1.391 (4)	C33—H33	0.9500
C31—C32	1.404 (4)	C35—H35	0.9500
C31—C37	1.474 (4)	C36—H36	0.9500
C32—C33	1.385 (5)	C42—H42	0.9500
C33—C34	1.369 (5)	C43—H43	0.9500
C34—C35	1.372 (4)	C46—H46	0.9500
C35—C36	1.385 (4)	C48—H48A	0.9900
C37—O38	1.213 (4)	C48—H48B	0.9900
C37—C39	1.535 (4)	C50—H50	0.9500
C39—O40	1.215 (4)	C51—H51	0.9500
C39—C41	1.495 (4)	C52—H52	0.9500
C41—C46	1.379 (4)	C53—H53	0.9500
C41—C42	1.393 (4)	C54—H54	0.9500
C42—C43	1.375 (4)
C6—C1—C2	119.4 (3)	C49—C50—C51	120.5 (3)
C6—C1—C7	122.8 (2)	C52—C51—C50	120.3 (3)
C2—C1—C7	117.8 (3)	C53—C52—C51	119.9 (3)
C3—C2—C1	120.8 (3)	C52—C53—C54	120.0 (3)
C4—C3—C2	117.9 (3)	C53—C54—C49	120.6 (3)
F1—C4—C5	119.1 (3)	C15—N17—H17	116.00
F1—C4—C3	118.2 (3)	C18—N17—H17	115.00
C5—C4—C3	122.7 (3)	C45—N47—H47	115.00
C4—C5—C6	119.0 (3)	C48—N47—H47	121.00
C5—C6—C1	120.1 (3)	C3—C2—H2	120.00
O8—C7—C1	122.7 (3)	C1—C2—H2	120.00
O8—C7—C9	118.5 (3)	C4—C3—H3	121.00
C1—C7—C9	118.5 (2)	C2—C3—H3	121.00
O10—C9—C11	122.8 (3)	C4—C5—H5	120.00
O10—C9—C7	117.0 (3)	C6—C5—H5	121.00
C11—C9—C7	120.0 (3)	C1—C6—H6	120.00
C12—C11—C16	119.6 (3)	C5—C6—H6	120.00
C12—C11—C9	123.7 (3)	C13—C12—H12	122.00
C16—C11—C9	116.7 (3)	C11—C12—H12	122.00
C13—C12—C11	116.9 (3)	N14—C13—H13	117.00
N14—C13—C12	125.0 (3)	C12—C13—H13	118.00
C13—N14—C15	117.9 (2)	C11—C16—H16	121.00
N14—C15—N17	115.9 (3)	C15—C16—H16	120.00
N14—C15—C16	121.6 (3)	H18A—C18—H18B	108.00
N17—C15—C16	122.5 (3)	C19—C18—H18A	109.00
C11—C16—C15	119.0 (3)	C19—C18—H18B	109.00
C15—N17—C18	120.8 (2)	N17—C18—H18A	109.00
N17—C18—C19	110.7 (2)	N17—C18—H18B	110.00
C24—C19—C20	118.7 (3)	C21—C20—H20	120.00
C24—C19—C18	120.3 (3)	C19—C20—H20	119.00
C20—C19—C18	121.1 (3)	C20—C21—H21	120.00
C21—C20—C19	120.8 (3)	C22—C21—H21	120.00
C20—C21—C22	119.5 (3)	C23—C22—H22	120.00
C23—C22—C21	119.9 (3)	C21—C22—H22	120.00
C22—C23—C24	120.8 (3)	C22—C23—H23	120.00
C23—C24—C19	120.3 (3)	C24—C23—H23	120.00
C36—C31—C32	119.4 (3)	C19—C24—H24	120.00
C36—C31—C37	121.6 (3)	C23—C24—H24	120.00
C32—C31—C37	119.0 (3)	C31—C32—H32	120.00
C33—C32—C31	120.2 (3)	C33—C32—H32	120.00
C34—C33—C32	118.1 (3)	C32—C33—H33	121.00
F2—C34—C33	118.2 (3)	C34—C33—H33	121.00
F2—C34—C35	118.0 (3)	C34—C35—H35	121.00
C33—C34—C35	123.7 (3)	C36—C35—H35	121.00
C34—C35—C36	118.0 (3)	C31—C36—H36	120.00
C35—C36—C31	120.5 (3)	C35—C36—H36	120.00
O38—C37—C31	124.1 (3)	C41—C42—H42	121.00
O38—C37—C39	117.3 (3)	C43—C42—H42	121.00
C31—C37—C39	118.4 (2)	N44—C43—H43	118.00
O40—C39—C41	123.1 (3)	C42—C43—H43	118.00
O40—C39—C37	117.6 (3)	C41—C46—H46	121.00
C41—C39—C37	119.2 (2)	C45—C46—H46	121.00
C46—C41—C42	120.3 (3)	N47—C48—H48A	109.00
C46—C41—C39	117.9 (3)	N47—C48—H48B	109.00
C42—C41—C39	121.7 (3)	C49—C48—H48A	109.00
C43—C42—C41	117.3 (3)	C49—C48—H48B	109.00
N44—C43—C42	124.3 (3)	H48A—C48—H48B	108.00
C43—N44—C45	118.2 (2)	C49—C50—H50	120.00
N44—C45—N47	116.0 (2)	C51—C50—H50	120.00
N44—C45—C46	121.2 (3)	C50—C51—H51	120.00
N47—C45—C46	122.8 (3)	C52—C51—H51	120.00
C41—C46—C45	118.6 (3)	C51—C52—H52	120.00
C45—N47—C48	121.1 (2)	C53—C52—H52	120.00
N47—C48—C49	111.3 (2)	C52—C53—H53	120.00
C50—C49—C54	118.8 (3)	C54—C53—H53	120.00
C50—C49—C48	121.3 (3)	C49—C54—H54	120.00
C54—C49—C48	119.9 (3)	C53—C54—H54	120.00
C13—N14—C15—C16	−1.7 (4)	C18—C19—C24—C23	−178.4 (3)
C15—N14—C13—C12	−0.9 (4)	C24—C19—C20—C21	−2.6 (5)
C13—N14—C15—N17	177.3 (3)	C19—C20—C21—C22	0.9 (5)
C18—N17—C15—N14	172.6 (3)	C20—C21—C22—C23	0.6 (6)
C18—N17—C15—C16	−8.5 (4)	C21—C22—C23—C24	−0.4 (6)
C15—N17—C18—C19	174.1 (3)	C22—C23—C24—C19	−1.3 (5)
C45—N44—C43—C42	0.4 (4)	C32—C31—C36—C35	−1.1 (5)
C43—N44—C45—C46	1.2 (4)	C32—C31—C37—O38	−5.4 (5)
C43—N44—C45—N47	−177.5 (3)	C37—C31—C32—C33	−177.2 (3)
C45—N47—C48—C49	−173.5 (3)	C36—C31—C32—C33	2.5 (5)
C48—N47—C45—C46	7.2 (4)	C36—C31—C37—O38	175.0 (3)
C48—N47—C45—N44	−174.1 (3)	C36—C31—C37—C39	−10.1 (4)
C2—C1—C6—C5	−1.0 (4)	C32—C31—C37—C39	169.5 (3)
C2—C1—C7—C9	−161.5 (3)	C37—C31—C36—C35	178.5 (3)
C2—C1—C7—O8	12.6 (4)	C31—C32—C33—C34	−0.8 (5)
C6—C1—C7—C9	19.6 (4)	C32—C33—C34—C35	−2.3 (5)
C7—C1—C2—C3	−177.7 (3)	C32—C33—C34—F2	178.4 (3)
C6—C1—C2—C3	1.3 (5)	F2—C34—C35—C36	−177.1 (3)
C7—C1—C6—C5	177.8 (3)	C33—C34—C35—C36	3.6 (5)
C6—C1—C7—O8	−166.3 (3)	C34—C35—C36—C31	−1.8 (5)
C1—C2—C3—C4	−0.7 (5)	C31—C37—C39—C41	126.0 (3)
C2—C3—C4—C5	−0.1 (6)	C31—C37—C39—O40	−57.3 (4)
C2—C3—C4—F1	−178.7 (3)	O38—C37—C39—O40	118.0 (3)
C3—C4—C5—C6	0.3 (6)	O38—C37—C39—C41	−58.8 (4)
F1—C4—C5—C6	178.9 (3)	O40—C39—C41—C42	176.1 (3)
C4—C5—C6—C1	0.3 (5)	C37—C39—C41—C46	176.7 (3)
C1—C7—C9—O10	41.8 (4)	C37—C39—C41—C42	−7.4 (4)
C1—C7—C9—C11	−142.6 (3)	O40—C39—C41—C46	0.2 (4)
O8—C7—C9—C11	43.0 (4)	C39—C41—C42—C43	−174.7 (3)
O8—C7—C9—O10	−132.6 (3)	C46—C41—C42—C43	1.1 (4)
C7—C9—C11—C12	13.7 (5)	C42—C41—C46—C45	0.4 (4)
O10—C9—C11—C16	7.2 (5)	C39—C41—C46—C45	176.3 (3)
C7—C9—C11—C16	−168.2 (3)	C41—C42—C43—N44	−1.5 (5)
O10—C9—C11—C12	−171.0 (3)	N44—C45—C46—C41	−1.6 (4)
C12—C11—C16—C15	0.3 (5)	N47—C45—C46—C41	177.1 (3)
C9—C11—C16—C15	−178.0 (3)	N47—C48—C49—C50	51.5 (4)
C9—C11—C12—C13	175.5 (3)	N47—C48—C49—C54	−130.3 (3)
C16—C11—C12—C13	−2.6 (4)	C48—C49—C50—C51	179.4 (3)
C11—C12—C13—N14	3.1 (4)	C54—C49—C50—C51	1.2 (5)
N17—C15—C16—C11	−176.9 (3)	C48—C49—C54—C53	−179.3 (3)
N14—C15—C16—C11	2.0 (4)	C50—C49—C54—C53	−1.1 (5)
N17—C18—C19—C24	129.3 (3)	C49—C50—C51—C52	−0.7 (5)
N17—C18—C19—C20	−51.8 (4)	C50—C51—C52—C53	0.0 (5)
C20—C19—C24—C23	2.7 (5)	C51—C52—C53—C54	0.2 (5)
C18—C19—C20—C21	178.6 (3)	C52—C53—C54—C49	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N44	0.94	2.10	3.037 (3)	174
N47—H47···N14	0.94	2.15	3.087 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯N44	0.94	2.10	3.037 (3)	174
N47—H47⋯N14	0.94	2.15	3.087 (4)	172