N-{4-[4-(4-Fluoro-phen-yl)-1-(2-methoxy-ethyl)-2-methyl-sulfanyl-1H-imidazol-5-yl]-2-pyrid-yl}-2-methyl-3-phenyl-propionamide.

In the crystal structure of the title compound, C(28)H(29)FN(4)O(2)S, the imidazole ring makes dihedral angles of 11.85 (7), 73.33 (7) and 22.83 (8)° with the 4-fluoro-phenyl, pyridine and phenyl rings, respectively. The 4-fluoro-phenyl ring makes dihedral angles of 77.91 (7) and 26.93 (8)° with the pyridine and phenyl rings, respectively. The phenyl and pyridine rings are nearly perpendicular, making a dihedral angle of 86.47 (9)°. The crystal packing shows an inter-molecular N-H⋯O hydrogen-bonding inter-action between the N-H and carbonyl groups of the amide functions.

Related literature

For related compounds and their biological activity, see: Laufer et al. (2004 ▶). For the biological activity of the title compound, see: Ziegler et al. (2009 ▶).

Experimental

Crystal data

C28H29FN4O2S

M = 504.61

Monoclinic,

a = 10.6254 (5) Å

b = 28.542 (1) Å

c = 9.8380 (4) Å

β = 117.953 (1)°

V = 2635.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 173 K

0.50 × 0.50 × 0.20 mm

Data collection

Bruker SMART with APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.685, T max = 0.746

21744 measured reflections

6183 independent reflections

6019 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.03

6183 reflections

328 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 3058 Friedel pairs

Flack parameter: 0.13 (4)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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/S1600536809048661/im2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048661/im2161Isup2.hkl

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

C28H29FN4O2S	F(000) = 1064
Mr = 504.61	Dx = 1.272 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9849 reflections
a = 10.6254 (5) Å	θ = 2.3–27.8°
b = 28.542 (1) Å	µ = 0.16 mm−1
c = 9.8380 (4) Å	T = 173 K
β = 117.953 (1)°	Plate, colourless
V = 2635.5 (2) Å3	0.50 × 0.50 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	6183 independent reflections
Radiation source: sealed Tube	6019 reflections with I > 2σ(I)
graphite	Rint = 0.020
CCD scan	θmax = 27.8°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
Tmin = 0.685, Tmax = 0.746	k = −36→36
21744 measured reflections	l = −12→12

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6111P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.003
6183 reflections	Δρmax = 0.27 e Å−3
328 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 3058 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (4)

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
C1	0.24375 (13)	0.39688 (4)	0.21997 (14)	0.0222 (2)
H1	0.2260	0.4140	0.1298	0.027*
C2	0.28100 (12)	0.34968 (4)	0.23423 (13)	0.0205 (2)
C3	0.30589 (15)	0.32580 (5)	0.36839 (15)	0.0281 (3)
H3	0.3316	0.2936	0.3816	0.034*
C4	0.29180 (17)	0.35060 (5)	0.48168 (16)	0.0331 (3)
H4	0.3079	0.3343	0.5726	0.040*
N5	0.25706 (13)	0.39587 (4)	0.47118 (13)	0.0295 (2)
C6	0.23312 (13)	0.41848 (4)	0.34154 (14)	0.0225 (2)
N7	0.19830 (12)	0.46584 (4)	0.34381 (12)	0.0262 (2)
H7	0.1880	0.4758	0.4166	0.031*
C8	0.17895 (15)	0.49964 (4)	0.23856 (15)	0.0268 (3)
O9	0.18466 (13)	0.49193 (3)	0.11861 (11)	0.0367 (2)
C10	0.15915 (17)	0.54895 (5)	0.28535 (17)	0.0317 (3)
H10	0.1283	0.5465	0.3667	0.038*
C11	0.30411 (19)	0.57371 (6)	0.35365 (19)	0.0403 (3)
H11A	0.2944	0.6056	0.3846	0.060*
H11B	0.3375	0.5751	0.2763	0.060*
H11C	0.3730	0.5563	0.4437	0.060*
C12	0.04625 (17)	0.57601 (5)	0.14924 (18)	0.0349 (3)
H12A	0.0524	0.6095	0.1780	0.042*
H12B	0.0682	0.5737	0.0621	0.042*
C13	−0.10448 (17)	0.55944 (5)	0.09573 (18)	0.0344 (3)
C14	−0.1682 (2)	0.52638 (6)	−0.0202 (2)	0.0451 (4)
H14	−0.1143	0.5122	−0.0635	0.054*
C15	−0.3093 (2)	0.51393 (7)	−0.0734 (3)	0.0575 (5)
H15	−0.3517	0.4915	−0.1537	0.069*
C16	−0.3892 (2)	0.53379 (7)	−0.0109 (3)	0.0623 (6)
H16	−0.4863	0.5253	−0.0484	0.075*
C17	−0.3265 (2)	0.56607 (7)	0.1068 (3)	0.0559 (5)
H17	−0.3806	0.5798	0.1506	0.067*
C18	−0.1852 (2)	0.57843 (6)	0.1611 (2)	0.0424 (4)
H18	−0.1424	0.6001	0.2437	0.051*
C19	0.29361 (12)	0.32572 (4)	0.10753 (13)	0.0203 (2)
N20	0.42522 (11)	0.31378 (4)	0.11967 (11)	0.0215 (2)
C21	0.39870 (12)	0.29288 (4)	−0.01583 (13)	0.0215 (2)
N22	0.26214 (11)	0.29049 (4)	−0.11212 (12)	0.0224 (2)
C23	0.19440 (13)	0.31074 (4)	−0.03559 (13)	0.0203 (2)
C24	0.56487 (13)	0.32057 (5)	0.25437 (14)	0.0254 (2)
H24A	0.6281	0.2944	0.2598	0.031*
H24B	0.5531	0.3194	0.3484	0.031*
C25	0.63583 (15)	0.36626 (5)	0.25252 (17)	0.0320 (3)
H25A	0.5692	0.3926	0.2341	0.038*
H25B	0.7210	0.3713	0.3532	0.038*
O26	0.67588 (14)	0.36466 (4)	0.13492 (14)	0.0423 (3)
C27	0.7462 (4)	0.40628 (8)	0.1299 (4)	0.0772 (8)
H27A	0.8367	0.4091	0.2247	0.116*
H27B	0.6859	0.4334	0.1204	0.116*
H27C	0.7645	0.4052	0.0412	0.116*
S28	0.53568 (3)	0.271151 (12)	−0.04958 (4)	0.03048 (8)
C29	0.43761 (19)	0.22789 (7)	−0.1920 (2)	0.0564 (6)
H29A	0.3579	0.2429	−0.2797	0.085*
H29B	0.4008	0.2042	−0.1475	0.085*
H29C	0.5004	0.2128	−0.2267	0.085*
C30	0.03784 (13)	0.31078 (4)	−0.11083 (14)	0.0210 (2)
C31	−0.03604 (13)	0.29825 (4)	−0.26672 (14)	0.0244 (2)
H31	0.0158	0.2916	−0.3212	0.029*
C32	−0.18352 (14)	0.29538 (5)	−0.34257 (15)	0.0287 (3)
H32	−0.2330	0.2862	−0.4476	0.034*
C34	−0.25631 (14)	0.30601 (5)	−0.26286 (16)	0.0299 (3)
C35	−0.18915 (14)	0.31932 (5)	−0.11006 (16)	0.0299 (3)
H35	−0.2426	0.3268	−0.0580	0.036*
C36	−0.04094 (14)	0.32145 (5)	−0.03438 (15)	0.0261 (3)
H36	0.0073	0.3303	0.0710	0.031*
F37	−0.40101 (9)	0.30368 (4)	−0.33851 (11)	0.0470 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0269 (6)	0.0217 (5)	0.0189 (5)	0.0019 (4)	0.0115 (4)	0.0007 (4)
C2	0.0211 (5)	0.0213 (5)	0.0175 (5)	−0.0001 (4)	0.0075 (4)	−0.0016 (4)
C3	0.0393 (7)	0.0210 (6)	0.0253 (6)	0.0048 (5)	0.0163 (5)	0.0033 (5)
C4	0.0508 (8)	0.0283 (7)	0.0243 (6)	0.0066 (6)	0.0210 (6)	0.0072 (5)
N5	0.0423 (6)	0.0281 (6)	0.0232 (5)	0.0056 (5)	0.0197 (5)	0.0013 (4)
C6	0.0258 (5)	0.0211 (6)	0.0224 (5)	0.0016 (4)	0.0129 (4)	−0.0002 (4)
N7	0.0392 (6)	0.0230 (5)	0.0226 (5)	0.0063 (4)	0.0196 (5)	−0.0012 (4)
C8	0.0366 (7)	0.0211 (6)	0.0263 (6)	0.0057 (5)	0.0177 (5)	0.0006 (5)
O9	0.0664 (7)	0.0250 (5)	0.0277 (5)	0.0096 (4)	0.0296 (5)	0.0035 (4)
C10	0.0481 (8)	0.0214 (6)	0.0323 (7)	0.0063 (5)	0.0244 (6)	−0.0012 (5)
C11	0.0530 (9)	0.0291 (7)	0.0381 (8)	0.0007 (6)	0.0207 (7)	−0.0063 (6)
C12	0.0496 (8)	0.0253 (6)	0.0385 (7)	0.0095 (6)	0.0278 (7)	0.0060 (6)
C13	0.0475 (8)	0.0233 (6)	0.0365 (7)	0.0095 (6)	0.0230 (6)	0.0070 (5)
C14	0.0605 (10)	0.0306 (7)	0.0449 (9)	0.0085 (7)	0.0254 (8)	0.0024 (6)
C15	0.0654 (12)	0.0364 (9)	0.0530 (10)	−0.0024 (8)	0.0130 (9)	0.0001 (8)
C16	0.0491 (11)	0.0429 (10)	0.0877 (16)	0.0014 (8)	0.0262 (11)	0.0206 (10)
C17	0.0613 (11)	0.0424 (10)	0.0804 (14)	0.0098 (8)	0.0469 (11)	0.0124 (9)
C18	0.0545 (10)	0.0321 (8)	0.0483 (9)	0.0076 (7)	0.0304 (8)	0.0035 (6)
C19	0.0226 (5)	0.0178 (5)	0.0206 (5)	0.0018 (4)	0.0101 (4)	0.0013 (4)
N20	0.0221 (5)	0.0215 (5)	0.0203 (5)	0.0007 (4)	0.0093 (4)	−0.0010 (4)
C21	0.0233 (6)	0.0210 (5)	0.0219 (5)	−0.0022 (4)	0.0121 (5)	−0.0024 (4)
N22	0.0244 (5)	0.0223 (5)	0.0217 (5)	0.0000 (4)	0.0118 (4)	−0.0013 (4)
C23	0.0256 (6)	0.0163 (5)	0.0194 (5)	0.0005 (4)	0.0109 (5)	0.0002 (4)
C24	0.0222 (5)	0.0295 (6)	0.0202 (5)	0.0001 (4)	0.0062 (4)	−0.0018 (4)
C25	0.0317 (7)	0.0298 (7)	0.0331 (7)	−0.0058 (5)	0.0140 (6)	−0.0099 (5)
O26	0.0589 (7)	0.0308 (5)	0.0498 (6)	−0.0129 (5)	0.0359 (6)	−0.0098 (5)
C27	0.129 (2)	0.0429 (10)	0.1070 (19)	−0.0351 (13)	0.0947 (19)	−0.0215 (12)
S28	0.02474 (14)	0.04109 (18)	0.03028 (15)	−0.00436 (13)	0.01678 (12)	−0.00972 (14)
C29	0.0352 (8)	0.0700 (12)	0.0673 (12)	−0.0093 (8)	0.0267 (8)	−0.0471 (10)
C30	0.0235 (5)	0.0166 (5)	0.0212 (5)	0.0001 (4)	0.0090 (4)	0.0017 (4)
C31	0.0261 (6)	0.0222 (6)	0.0231 (6)	0.0036 (4)	0.0100 (5)	−0.0009 (4)
C32	0.0273 (6)	0.0277 (6)	0.0230 (6)	0.0003 (5)	0.0051 (5)	−0.0017 (5)
C34	0.0220 (6)	0.0307 (6)	0.0306 (7)	−0.0028 (5)	0.0069 (5)	0.0023 (5)
C35	0.0270 (6)	0.0364 (7)	0.0299 (7)	−0.0043 (5)	0.0165 (5)	−0.0004 (5)
C36	0.0265 (6)	0.0304 (7)	0.0208 (5)	−0.0042 (5)	0.0106 (5)	−0.0006 (4)
F37	0.0225 (4)	0.0728 (7)	0.0388 (5)	−0.0065 (4)	0.0086 (4)	−0.0028 (5)

C1—C2	1.3926 (16)	C18—H18	0.9500
C1—C6	1.3963 (17)	C19—C23	1.3730 (16)
C1—H1	0.9500	C19—N20	1.3891 (15)
C2—C3	1.3962 (17)	N20—C21	1.3638 (15)
C2—C19	1.4818 (16)	N20—C24	1.4670 (15)
C3—C4	1.3865 (19)	C21—N22	1.3111 (16)
C3—H3	0.9500	C21—S28	1.7511 (12)
C4—N5	1.3344 (18)	N22—C23	1.3882 (15)
C4—H4	0.9500	C23—C30	1.4700 (16)
N5—C6	1.3429 (16)	C24—C25	1.5106 (19)
C6—N7	1.4047 (16)	C24—H24A	0.9900
N7—C8	1.3584 (17)	C24—H24B	0.9900
N7—H7	0.8242	C25—O26	1.4083 (18)
C8—O9	1.2295 (16)	C25—H25A	0.9900
C8—C10	1.5257 (17)	C25—H25B	0.9900
C10—C12	1.524 (2)	O26—C27	1.416 (2)
C10—C11	1.534 (2)	C27—H27A	0.9800
C10—H10	1.0000	C27—H27B	0.9800
C11—H11A	0.9800	C27—H27C	0.9800
C11—H11B	0.9800	S28—C29	1.7902 (16)
C11—H11C	0.9800	C29—H29A	0.9800
C12—C13	1.508 (2)	C29—H29B	0.9800
C12—H12A	0.9900	C29—H29C	0.9800
C12—H12B	0.9900	C30—C36	1.3962 (18)
C13—C14	1.388 (2)	C30—C31	1.4026 (16)
C13—C18	1.400 (2)	C31—C32	1.3867 (18)
C14—C15	1.383 (3)	C31—H31	0.9500
C14—H14	0.9500	C32—C34	1.369 (2)
C15—C16	1.382 (3)	C32—H32	0.9500
C15—H15	0.9500	C34—F37	1.3599 (15)
C16—C17	1.382 (3)	C34—C35	1.381 (2)
C16—H16	0.9500	C35—C36	1.3924 (18)
C17—C18	1.383 (3)	C35—H35	0.9500
C17—H17	0.9500	C36—H36	0.9500
C2—C1—C6	118.29 (11)	C23—C19—N20	105.65 (10)
C2—C1—H1	120.9	C23—C19—C2	132.66 (11)
C6—C1—H1	120.9	N20—C19—C2	121.69 (10)
C1—C2—C3	119.11 (11)	C21—N20—C19	106.55 (10)
C1—C2—C19	119.69 (10)	C21—N20—C24	126.79 (10)
C3—C2—C19	121.20 (11)	C19—N20—C24	126.61 (10)
C4—C3—C2	117.82 (11)	N22—C21—N20	112.37 (10)
C4—C3—H3	121.1	N22—C21—S28	125.54 (9)
C2—C3—H3	121.1	N20—C21—S28	122.07 (9)
N5—C4—C3	124.21 (12)	C21—N22—C23	105.42 (10)
N5—C4—H4	117.9	C19—C23—N22	109.99 (10)
C3—C4—H4	117.9	C19—C23—C30	131.29 (11)
C4—N5—C6	117.46 (11)	N22—C23—C30	118.63 (10)
N5—C6—C1	123.09 (11)	N20—C24—C25	113.73 (11)
N5—C6—N7	112.43 (11)	N20—C24—H24A	108.8
C1—C6—N7	124.48 (11)	C25—C24—H24A	108.8
C8—N7—C6	128.19 (11)	N20—C24—H24B	108.8
C8—N7—H7	112.5	C25—C24—H24B	108.8
C6—N7—H7	119.3	H24A—C24—H24B	107.7
O9—C8—N7	123.12 (11)	O26—C25—C24	109.06 (11)
O9—C8—C10	122.05 (12)	O26—C25—H25A	109.9
N7—C8—C10	114.71 (11)	C24—C25—H25A	109.9
C12—C10—C8	111.44 (12)	O26—C25—H25B	109.9
C12—C10—C11	111.51 (12)	C24—C25—H25B	109.9
C8—C10—C11	107.76 (12)	H25A—C25—H25B	108.3
C12—C10—H10	108.7	C25—O26—C27	111.64 (14)
C8—C10—H10	108.7	O26—C27—H27A	109.5
C11—C10—H10	108.7	O26—C27—H27B	109.5
C10—C11—H11A	109.5	H27A—C27—H27B	109.5
C10—C11—H11B	109.5	O26—C27—H27C	109.5
H11A—C11—H11B	109.5	H27A—C27—H27C	109.5
C10—C11—H11C	109.5	H27B—C27—H27C	109.5
H11A—C11—H11C	109.5	C21—S28—C29	99.33 (7)
H11B—C11—H11C	109.5	S28—C29—H29A	109.5
C13—C12—C10	114.68 (12)	S28—C29—H29B	109.5
C13—C12—H12A	108.6	H29A—C29—H29B	109.5
C10—C12—H12A	108.6	S28—C29—H29C	109.5
C13—C12—H12B	108.6	H29A—C29—H29C	109.5
C10—C12—H12B	108.6	H29B—C29—H29C	109.5
H12A—C12—H12B	107.6	C36—C30—C31	118.36 (11)
C14—C13—C18	118.23 (17)	C36—C30—C23	123.48 (11)
C14—C13—C12	121.94 (14)	C31—C30—C23	118.14 (11)
C18—C13—C12	119.81 (14)	C32—C31—C30	121.03 (12)
C15—C14—C13	120.69 (18)	C32—C31—H31	119.5
C15—C14—H14	119.7	C30—C31—H31	119.5
C13—C14—H14	119.7	C34—C32—C31	118.56 (12)
C16—C15—C14	120.62 (19)	C34—C32—H32	120.7
C16—C15—H15	119.7	C31—C32—H32	120.7
C14—C15—H15	119.7	F37—C34—C32	118.24 (12)
C17—C16—C15	119.40 (19)	F37—C34—C35	118.93 (13)
C17—C16—H16	120.3	C32—C34—C35	122.82 (12)
C15—C16—H16	120.3	C34—C35—C36	118.15 (12)
C16—C17—C18	120.22 (19)	C34—C35—H35	120.9
C16—C17—H17	119.9	C36—C35—H35	120.9
C18—C17—H17	119.9	C35—C36—C30	121.06 (12)
C17—C18—C13	120.78 (17)	C35—C36—H36	119.5
C17—C18—H18	119.6	C30—C36—H36	119.5
C13—C18—H18	119.6
C6—C1—C2—C3	0.14 (18)	C2—C19—N20—C21	−179.52 (10)
C6—C1—C2—C19	−179.83 (11)	C23—C19—N20—C24	−177.12 (11)
C1—C2—C3—C4	0.12 (19)	C2—C19—N20—C24	2.80 (18)
C19—C2—C3—C4	−179.91 (12)	C19—N20—C21—N22	−0.15 (14)
C2—C3—C4—N5	−0.5 (2)	C24—N20—C21—N22	177.53 (11)
C3—C4—N5—C6	0.6 (2)	C19—N20—C21—S28	−178.85 (9)
C4—N5—C6—C1	−0.4 (2)	C24—N20—C21—S28	−1.17 (18)
C4—N5—C6—N7	−179.66 (13)	N20—C21—N22—C23	−0.33 (14)
C2—C1—C6—N5	−0.02 (19)	S28—C21—N22—C23	178.31 (9)
C2—C1—C6—N7	179.20 (11)	N20—C19—C23—N22	−0.79 (13)
N5—C6—N7—C8	174.22 (13)	C2—C19—C23—N22	179.31 (12)
C1—C6—N7—C8	−5.1 (2)	N20—C19—C23—C30	175.68 (12)
C6—N7—C8—O9	3.0 (2)	C2—C19—C23—C30	−4.2 (2)
C6—N7—C8—C10	−173.10 (13)	C21—N22—C23—C19	0.70 (13)
O9—C8—C10—C12	43.35 (19)	C21—N22—C23—C30	−176.27 (10)
N7—C8—C10—C12	−140.48 (13)	C21—N20—C24—C25	90.03 (15)
O9—C8—C10—C11	−79.29 (17)	C19—N20—C24—C25	−92.74 (15)
N7—C8—C10—C11	96.87 (14)	N20—C24—C25—O26	−68.96 (15)
C8—C10—C12—C13	71.17 (16)	C24—C25—O26—C27	−178.65 (19)
C11—C10—C12—C13	−168.37 (12)	N22—C21—S28—C29	−23.44 (14)
C10—C12—C13—C14	−92.71 (17)	N20—C21—S28—C29	155.08 (13)
C10—C12—C13—C18	88.86 (17)	C19—C23—C30—C36	−9.4 (2)
C18—C13—C14—C15	2.4 (2)	N22—C23—C30—C36	166.83 (11)
C12—C13—C14—C15	−176.06 (16)	C19—C23—C30—C31	172.30 (12)
C13—C14—C15—C16	−0.8 (3)	N22—C23—C30—C31	−11.49 (16)
C14—C15—C16—C17	−0.6 (3)	C36—C30—C31—C32	−1.56 (19)
C15—C16—C17—C18	0.2 (3)	C23—C30—C31—C32	176.85 (11)
C16—C17—C18—C13	1.5 (3)	C30—C31—C32—C34	1.4 (2)
C14—C13—C18—C17	−2.8 (2)	C31—C32—C34—F37	179.18 (13)
C12—C13—C18—C17	175.69 (15)	C31—C32—C34—C35	−0.2 (2)
C1—C2—C19—C23	−73.36 (17)	F37—C34—C35—C36	179.91 (13)
C3—C2—C19—C23	106.68 (16)	C32—C34—C35—C36	−0.7 (2)
C1—C2—C19—N20	106.75 (13)	C34—C35—C36—C30	0.5 (2)
C3—C2—C19—N20	−73.21 (16)	C31—C30—C36—C35	0.62 (19)
C23—C19—N20—C21	0.57 (12)	C23—C30—C36—C35	−177.70 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O9i	0.82	2.21	3.025 (1)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O9i	0.82	2.21	3.025 (1)	173

Symmetry code: (i) .