2-(2,4-Di-fluoro-phen-yl)-4,5-dimethyl-1-(4-methyl-phen-yl)-1H-imidazole monohydrate.

The asymmetric unit of the title compound, C18H16F2N2·H2O, contains two independent mol-ecules (A and B), and two independent water mol-ecules of crystallization. In mol-ecule A, the imidazole ring makes dihedral angles of 47.46 (7) and 60.98 (6)° with the 2,4-di-fluoro-phenyl and methyl-phenyl rings, respectively. The corresponding angles in mol-ecule B are 45.85 (7) and 62.78 (7)°, respectively. The dihedral angle between the two benzene rings is 64.98 (7)° in mol-ecule A and 65.53 (7)° in mol-ecule B. In the crystal, the two independent mol-ecules are linked by O-H⋯N and O-H⋯O hydrogen bonds, forming chains propagating along [100]. These chains are linked via C-H⋯F hydrogen bonds, forming slab-like two-dimensional networks lying parallel to (001).

Related literature

For background and the biological properties of imidazole derivatives, see: Dutta et al. (2009 ▶); Hori et al. (2000 ▶); Khabnadideh et al. (2003 ▶); Mamolo et al. (2004 ▶); Quattara et al. (1987 ▶); Sengupta & Bhattacharya (1983 ▶); Ucucu et al. (2001 ▶); Noilada et al. (2004 ▶). For related structures, see: Rizwana et al. (2013 ▶); Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C18H16F2N2·H2O

M = 316.34

Triclinic,

a = 7.9424 (9) Å

b = 14.5238 (16) Å

c = 14.6561 (16) Å

α = 75.087 (2)°

β = 89.990 (2)°

γ = 86.012 (2)°

V = 1629.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

18763 measured reflections

7545 independent reflections

5782 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.00

7545 reflections

433 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813026354/su2650sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026354/su2650Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026354/su2650Isup3.cml

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

C18H16F2N2·H2O	Z = 4
Mr = 316.34	F(000) = 664
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9424 (9) Å	Cell parameters from 5735 reflections
b = 14.5238 (16) Å	θ = 2–25°
c = 14.6561 (16) Å	µ = 0.10 mm−1
α = 75.087 (2)°	T = 294 K
β = 89.990 (2)°	Prism, colourless
γ = 86.012 (2)°	0.30 × 0.25 × 0.20 mm
V = 1629.5 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	5782 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.1°, θmin = 1.8°
ω scan	h = −10→10
18763 measured reflections	k = −18→18
7545 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.427P] where P = (Fo2 + 2Fc2)/3
7545 reflections	(Δ/σ)max = 0.003
433 parameters	Δρmax = 0.26 e Å−3
13 restraints	Δρmin = −0.26 e Å−3

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 esds are taken into account in the estimation of distances, angles and torsion angles

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	0.71950 (16)	0.40164 (7)	0.19658 (7)	0.0736 (4)
F2	0.85905 (19)	0.38610 (9)	0.50961 (9)	0.0903 (5)
N1	0.76753 (15)	0.21495 (9)	0.14701 (8)	0.0430 (4)
N3	0.58511 (15)	0.13746 (9)	0.24705 (9)	0.0466 (4)
C2	0.69990 (18)	0.20050 (10)	0.23469 (10)	0.0427 (4)
C4	0.57872 (18)	0.10945 (10)	0.16402 (11)	0.0461 (4)
C5	0.68894 (18)	0.15611 (10)	0.10096 (10)	0.0445 (4)
C6	0.7308 (2)	0.15112 (14)	0.00357 (12)	0.0594 (6)
C7	0.4597 (2)	0.03776 (13)	0.15297 (14)	0.0620 (6)
C8	0.91789 (17)	0.26239 (10)	0.11653 (10)	0.0418 (4)
C9	1.06498 (19)	0.23288 (11)	0.16966 (11)	0.0477 (5)
C10	1.21032 (19)	0.27847 (12)	0.14079 (12)	0.0530 (5)
C11	1.2127 (2)	0.35199 (12)	0.06008 (12)	0.0524 (5)
C12	1.0649 (2)	0.38001 (12)	0.00716 (12)	0.0548 (5)
C13	0.9174 (2)	0.33543 (12)	0.03523 (11)	0.0511 (5)
C14	1.3728 (3)	0.40089 (18)	0.03046 (16)	0.0807 (8)
C15	0.74677 (18)	0.25045 (10)	0.30559 (10)	0.0443 (4)
C16	0.7547 (2)	0.34818 (11)	0.28531 (11)	0.0519 (5)
C17	0.7926 (3)	0.39549 (13)	0.35225 (13)	0.0620 (6)
C18	0.8220 (2)	0.34102 (14)	0.44250 (13)	0.0616 (6)
C19	0.8149 (2)	0.24426 (13)	0.46788 (12)	0.0633 (6)
C20	0.7775 (2)	0.19936 (12)	0.39909 (11)	0.0539 (5)
F3	0.2298 (2)	0.39845 (7)	0.59771 (8)	0.0862 (5)
F4	0.36352 (18)	0.38368 (9)	0.29162 (8)	0.0829 (4)
N4	0.27463 (15)	0.21484 (9)	0.74141 (8)	0.0440 (4)
N5	0.09244 (16)	0.13610 (9)	0.68227 (9)	0.0480 (4)
C21	0.20702 (18)	0.19931 (10)	0.66138 (10)	0.0438 (4)
C22	0.08604 (19)	0.10927 (11)	0.77972 (11)	0.0472 (4)
C23	0.19611 (18)	0.15691 (11)	0.81797 (10)	0.0453 (4)
C24	0.2371 (2)	0.15352 (14)	0.91762 (11)	0.0597 (6)
C25	−0.0326 (2)	0.03794 (13)	0.82822 (14)	0.0631 (6)
C26	0.42484 (18)	0.26301 (10)	0.74711 (10)	0.0436 (4)
C27	0.4225 (2)	0.33889 (12)	0.78742 (12)	0.0513 (5)
C28	0.5694 (2)	0.38378 (12)	0.79244 (12)	0.0563 (5)
C29	0.7196 (2)	0.35333 (13)	0.75702 (11)	0.0539 (5)
C30	0.7183 (2)	0.27746 (13)	0.71679 (12)	0.0567 (5)
C31	0.5731 (2)	0.23190 (11)	0.71129 (11)	0.0510 (5)
C32	0.8800 (2)	0.40155 (17)	0.76255 (16)	0.0783 (8)
C33	0.25271 (19)	0.24827 (10)	0.56501 (10)	0.0452 (4)
C34	0.2631 (2)	0.34591 (12)	0.53533 (11)	0.0556 (5)
C35	0.3013 (3)	0.39309 (12)	0.44469 (12)	0.0640 (6)
C36	0.3268 (2)	0.33864 (13)	0.38162 (12)	0.0587 (5)
C37	0.3160 (2)	0.24260 (13)	0.40541 (12)	0.0604 (6)
C38	0.2789 (2)	0.19759 (12)	0.49714 (11)	0.0527 (5)
O1W	0.9309 (2)	0.00201 (13)	0.59088 (13)	0.0898 (7)
O2W	0.4297 (2)	0.00074 (12)	0.40813 (12)	0.0872 (6)
H6A	0.68540	0.09580	−0.00860	0.0890*
H6B	0.85120	0.14680	−0.00280	0.0890*
H6C	0.68290	0.20750	−0.04080	0.0890*
H7A	0.34580	0.06540	0.15020	0.0930*
H7B	0.47300	−0.01730	0.20590	0.0930*
H7C	0.48360	0.01910	0.09580	0.0930*
H9	1.06610	0.18300	0.22420	0.0570*
H10	1.30890	0.25890	0.17680	0.0640*
H12	1.06440	0.42930	−0.04790	0.0660*
H13	0.81870	0.35490	−0.00080	0.0610*
H14A	1.46100	0.35430	0.02430	0.1210*
H14B	1.40560	0.43210	0.07730	0.1210*
H14C	1.35380	0.44730	−0.02900	0.1210*
H17	0.79790	0.46150	0.33670	0.0740*
H19	0.83490	0.20940	0.53010	0.0760*
H20	0.77270	0.13340	0.41540	0.0650*
H24A	0.19330	0.09800	0.95860	0.0900*
H24B	0.18710	0.20980	0.93260	0.0900*
H24C	0.35740	0.15050	0.92620	0.0900*
H25A	−0.01050	0.02150	0.89510	0.0950*
H25B	−0.01700	−0.01840	0.80540	0.0950*
H25C	−0.14670	0.06480	0.81540	0.0950*
H27	0.32270	0.36000	0.81120	0.0620*
H28	0.56740	0.43490	0.81980	0.0680*
H30	0.81780	0.25640	0.69270	0.0680*
H31	0.57500	0.18080	0.68380	0.0610*
H32A	0.85530	0.45710	0.78560	0.1170*
H32B	0.92750	0.42030	0.70080	0.1170*
H32C	0.95930	0.35800	0.80470	0.1170*
H35	0.30950	0.45890	0.42700	0.0770*
H37	0.33340	0.20780	0.36060	0.0720*
H38	0.27110	0.13180	0.51400	0.0630*
H1WA	0.974 (4)	0.0404 (19)	0.614 (2)	0.1350*
H1WB	0.9002 (18)	0.012 (2)	0.5427 (11)	0.1350*
H2WA	0.471 (4)	0.0423 (18)	0.3654 (17)	0.1310*
H2WB	0.4005 (19)	0.012 (2)	0.4516 (11)	0.1310*

	U11	U22	U33	U12	U13	U23
F1	0.1162 (9)	0.0530 (6)	0.0492 (6)	−0.0004 (6)	−0.0032 (6)	−0.0104 (4)
F2	0.1257 (11)	0.0887 (8)	0.0712 (7)	−0.0075 (7)	−0.0156 (7)	−0.0475 (7)
N1	0.0397 (6)	0.0493 (7)	0.0430 (6)	−0.0093 (5)	0.0014 (5)	−0.0155 (5)
N3	0.0430 (6)	0.0493 (7)	0.0487 (7)	−0.0082 (5)	0.0039 (5)	−0.0138 (5)
C2	0.0404 (7)	0.0456 (7)	0.0429 (7)	−0.0048 (6)	0.0016 (6)	−0.0127 (6)
C4	0.0415 (7)	0.0480 (8)	0.0512 (8)	−0.0057 (6)	−0.0010 (6)	−0.0167 (6)
C5	0.0402 (7)	0.0483 (8)	0.0482 (8)	−0.0058 (6)	−0.0019 (6)	−0.0178 (6)
C6	0.0597 (10)	0.0740 (11)	0.0536 (9)	−0.0172 (8)	0.0050 (7)	−0.0296 (8)
C7	0.0578 (10)	0.0644 (10)	0.0700 (11)	−0.0231 (8)	0.0033 (8)	−0.0236 (9)
C8	0.0384 (7)	0.0455 (7)	0.0449 (7)	−0.0083 (6)	0.0039 (6)	−0.0167 (6)
C9	0.0456 (8)	0.0493 (8)	0.0486 (8)	−0.0042 (6)	−0.0018 (6)	−0.0129 (6)
C10	0.0393 (8)	0.0667 (10)	0.0581 (9)	−0.0061 (7)	−0.0033 (6)	−0.0246 (8)
C11	0.0478 (8)	0.0619 (9)	0.0562 (9)	−0.0184 (7)	0.0099 (7)	−0.0274 (8)
C12	0.0591 (10)	0.0555 (9)	0.0494 (8)	−0.0146 (7)	0.0057 (7)	−0.0099 (7)
C13	0.0451 (8)	0.0572 (9)	0.0494 (8)	−0.0066 (7)	−0.0027 (6)	−0.0099 (7)
C14	0.0623 (11)	0.1094 (17)	0.0801 (13)	−0.0417 (11)	0.0171 (10)	−0.0329 (12)
C15	0.0424 (7)	0.0488 (8)	0.0444 (7)	−0.0048 (6)	0.0027 (6)	−0.0165 (6)
C16	0.0622 (10)	0.0497 (8)	0.0444 (8)	−0.0031 (7)	0.0029 (7)	−0.0133 (7)
C17	0.0801 (12)	0.0506 (9)	0.0606 (10)	−0.0072 (8)	0.0034 (9)	−0.0235 (8)
C18	0.0678 (11)	0.0704 (11)	0.0566 (10)	−0.0033 (8)	−0.0039 (8)	−0.0348 (9)
C19	0.0781 (12)	0.0663 (11)	0.0454 (9)	0.0036 (9)	−0.0087 (8)	−0.0168 (8)
C20	0.0630 (10)	0.0507 (8)	0.0480 (8)	−0.0011 (7)	−0.0011 (7)	−0.0135 (7)
F3	0.1543 (12)	0.0521 (6)	0.0568 (6)	0.0050 (6)	−0.0037 (7)	−0.0254 (5)
F4	0.1083 (9)	0.0851 (8)	0.0496 (6)	−0.0118 (7)	0.0139 (6)	−0.0059 (5)
N4	0.0427 (6)	0.0486 (7)	0.0430 (6)	−0.0066 (5)	0.0031 (5)	−0.0149 (5)
N5	0.0468 (7)	0.0501 (7)	0.0503 (7)	−0.0052 (5)	0.0013 (5)	−0.0181 (6)
C21	0.0440 (7)	0.0448 (7)	0.0449 (7)	−0.0011 (6)	0.0014 (6)	−0.0164 (6)
C22	0.0424 (7)	0.0486 (8)	0.0512 (8)	−0.0038 (6)	0.0041 (6)	−0.0136 (6)
C23	0.0412 (7)	0.0496 (8)	0.0453 (7)	−0.0040 (6)	0.0047 (6)	−0.0125 (6)
C24	0.0602 (10)	0.0737 (11)	0.0455 (8)	−0.0151 (8)	0.0042 (7)	−0.0134 (8)
C25	0.0589 (10)	0.0648 (11)	0.0675 (11)	−0.0197 (8)	0.0078 (8)	−0.0164 (9)
C26	0.0408 (7)	0.0478 (7)	0.0419 (7)	−0.0058 (6)	0.0016 (6)	−0.0103 (6)
C27	0.0447 (8)	0.0591 (9)	0.0556 (9)	−0.0072 (7)	0.0071 (7)	−0.0237 (7)
C28	0.0571 (9)	0.0599 (9)	0.0569 (9)	−0.0135 (7)	0.0013 (7)	−0.0216 (8)
C29	0.0450 (8)	0.0660 (10)	0.0463 (8)	−0.0119 (7)	−0.0028 (6)	−0.0045 (7)
C30	0.0404 (8)	0.0686 (10)	0.0569 (9)	0.0010 (7)	0.0054 (7)	−0.0100 (8)
C31	0.0491 (8)	0.0525 (8)	0.0517 (8)	0.0002 (7)	0.0050 (7)	−0.0148 (7)
C32	0.0528 (10)	0.1039 (16)	0.0762 (13)	−0.0268 (10)	−0.0046 (9)	−0.0139 (11)
C33	0.0451 (8)	0.0476 (8)	0.0441 (7)	−0.0022 (6)	−0.0002 (6)	−0.0144 (6)
C34	0.0728 (11)	0.0499 (8)	0.0474 (8)	−0.0005 (7)	−0.0043 (7)	−0.0196 (7)
C35	0.0867 (13)	0.0491 (9)	0.0543 (10)	−0.0092 (8)	−0.0042 (9)	−0.0090 (7)
C36	0.0619 (10)	0.0673 (10)	0.0435 (8)	−0.0055 (8)	0.0041 (7)	−0.0081 (7)
C37	0.0719 (11)	0.0641 (10)	0.0487 (9)	0.0036 (8)	0.0065 (8)	−0.0232 (8)
C38	0.0609 (9)	0.0492 (8)	0.0504 (8)	−0.0018 (7)	0.0034 (7)	−0.0179 (7)
O1W	0.0968 (12)	0.0877 (11)	0.0974 (12)	−0.0125 (9)	−0.0135 (9)	−0.0449 (10)
O2W	0.0945 (11)	0.0827 (10)	0.0774 (10)	−0.0101 (8)	0.0206 (8)	−0.0070 (8)

F1—C16	1.3500 (19)	C10—H10	0.9300
F2—C18	1.357 (2)	C12—H12	0.9300
F3—C34	1.349 (2)	C13—H13	0.9300
F4—C36	1.355 (2)	C14—H14C	0.9600
O1W—H1WB	0.722 (16)	C14—H14A	0.9600
O1W—H1WA	0.82 (3)	C14—H14B	0.9600
O2W—H2WB	0.73 (2)	C17—H17	0.9300
O2W—H2WA	0.84 (3)	C19—H19	0.9300
N1—C5	1.3952 (19)	C20—H20	0.9300
N1—C8	1.4340 (18)	C21—C33	1.467 (2)
N1—C2	1.3640 (18)	C22—C23	1.357 (2)
N3—C2	1.3164 (19)	C22—C25	1.491 (2)
N3—C4	1.381 (2)	C23—C24	1.484 (2)
N4—C23	1.3938 (19)	C26—C27	1.377 (2)
N4—C26	1.4374 (19)	C26—C31	1.384 (2)
N4—C21	1.3668 (19)	C27—C28	1.387 (2)
N5—C21	1.318 (2)	C28—C29	1.390 (2)
N5—C22	1.382 (2)	C29—C32	1.508 (3)
C2—C15	1.473 (2)	C29—C30	1.378 (3)
C4—C5	1.356 (2)	C30—C31	1.381 (2)
C4—C7	1.493 (2)	C33—C34	1.381 (2)
C5—C6	1.484 (2)	C33—C38	1.389 (2)
C8—C13	1.376 (2)	C34—C35	1.374 (2)
C8—C9	1.383 (2)	C35—C36	1.369 (3)
C9—C10	1.383 (2)	C36—C37	1.357 (3)
C10—C11	1.376 (2)	C37—C38	1.377 (2)
C11—C14	1.509 (3)	C24—H24A	0.9600
C11—C12	1.384 (2)	C24—H24B	0.9600
C12—C13	1.389 (2)	C24—H24C	0.9600
C15—C16	1.379 (2)	C25—H25C	0.9600
C15—C20	1.393 (2)	C25—H25A	0.9600
C16—C17	1.379 (3)	C25—H25B	0.9600
C17—C18	1.366 (3)	C27—H27	0.9300
C18—C19	1.363 (3)	C28—H28	0.9300
C19—C20	1.377 (2)	C30—H30	0.9300
C6—H6C	0.9600	C31—H31	0.9300
C6—H6B	0.9600	C32—H32A	0.9600
C6—H6A	0.9600	C32—H32B	0.9600
C7—H7C	0.9600	C32—H32C	0.9600
C7—H7A	0.9600	C35—H35	0.9300
C7—H7B	0.9600	C37—H37	0.9300
C9—H9	0.9300	C38—H38	0.9300
H1WA—O1W—H1WB	125 (3)	C16—C17—H17	122.00
H2WA—O2W—H2WB	121 (3)	C18—C19—H19	121.00
C5—N1—C8	125.27 (12)	C20—C19—H19	121.00
C2—N1—C5	107.05 (12)	C19—C20—H20	119.00
C2—N1—C8	126.05 (12)	C15—C20—H20	119.00
C2—N3—C4	105.81 (12)	N5—C21—C33	124.47 (13)
C23—N4—C26	125.20 (12)	N4—C21—C33	124.54 (13)
C21—N4—C23	107.14 (12)	N4—C21—N5	110.98 (13)
C21—N4—C26	126.10 (12)	C23—C22—C25	129.00 (15)
C21—N5—C22	105.96 (13)	N5—C22—C25	120.43 (14)
N3—C2—C15	124.42 (13)	N5—C22—C23	110.56 (13)
N1—C2—N3	111.20 (13)	N4—C23—C22	105.36 (13)
N1—C2—C15	124.37 (13)	N4—C23—C24	123.10 (14)
N3—C4—C7	120.38 (14)	C22—C23—C24	131.53 (14)
N3—C4—C5	110.69 (13)	N4—C26—C27	120.98 (13)
C5—C4—C7	128.92 (15)	C27—C26—C31	120.14 (14)
C4—C5—C6	131.75 (14)	N4—C26—C31	118.88 (13)
N1—C5—C4	105.25 (12)	C26—C27—C28	119.81 (15)
N1—C5—C6	123.00 (13)	C27—C28—C29	120.84 (16)
N1—C8—C9	118.94 (13)	C30—C29—C32	120.69 (16)
N1—C8—C13	120.88 (13)	C28—C29—C30	118.17 (15)
C9—C8—C13	120.18 (14)	C28—C29—C32	121.14 (17)
C8—C9—C10	119.23 (15)	C29—C30—C31	121.73 (15)
C9—C10—C11	121.64 (15)	C26—C31—C30	119.32 (15)
C12—C11—C14	121.01 (17)	C21—C33—C38	120.50 (14)
C10—C11—C12	118.42 (15)	C34—C33—C38	116.59 (14)
C10—C11—C14	120.57 (16)	C21—C33—C34	122.82 (14)
C11—C12—C13	120.81 (16)	C33—C34—C35	123.51 (16)
C8—C13—C12	119.72 (15)	F3—C34—C33	118.53 (14)
C2—C15—C16	123.06 (13)	F3—C34—C35	117.94 (16)
C16—C15—C20	116.83 (14)	C34—C35—C36	116.79 (17)
C2—C15—C20	120.04 (14)	F4—C36—C37	119.22 (16)
C15—C16—C17	123.20 (15)	C35—C36—C37	122.91 (16)
F1—C16—C17	117.44 (15)	F4—C36—C35	117.87 (17)
F1—C16—C15	119.34 (14)	C36—C37—C38	118.70 (17)
C16—C17—C18	116.94 (18)	C33—C38—C37	121.48 (16)
F2—C18—C19	118.95 (16)	C23—C24—H24A	110.00
F2—C18—C17	117.96 (18)	H24A—C24—H24B	109.00
C17—C18—C19	123.10 (18)	H24A—C24—H24C	109.00
C18—C19—C20	118.38 (16)	H24B—C24—H24C	110.00
C15—C20—C19	121.56 (16)	C23—C24—H24B	109.00
C5—C6—H6A	109.00	C23—C24—H24C	109.00
H6B—C6—H6C	110.00	C22—C25—H25A	109.00
C5—C6—H6C	109.00	H25A—C25—H25B	110.00
H6A—C6—H6B	109.00	C22—C25—H25B	109.00
C5—C6—H6B	109.00	C22—C25—H25C	109.00
H6A—C6—H6C	109.00	H25B—C25—H25C	109.00
C4—C7—H7C	110.00	H25A—C25—H25C	109.00
H7A—C7—H7B	109.00	C28—C27—H27	120.00
C4—C7—H7B	109.00	C26—C27—H27	120.00
C4—C7—H7A	109.00	C27—C28—H28	120.00
H7A—C7—H7C	110.00	C29—C28—H28	120.00
H7B—C7—H7C	109.00	C29—C30—H30	119.00
C8—C9—H9	120.00	C31—C30—H30	119.00
C10—C9—H9	120.00	C26—C31—H31	120.00
C11—C10—H10	119.00	C30—C31—H31	120.00
C9—C10—H10	119.00	C29—C32—H32B	109.00
C11—C12—H12	120.00	C29—C32—H32A	109.00
C13—C12—H12	120.00	H32A—C32—H32C	110.00
C8—C13—H13	120.00	C29—C32—H32C	109.00
C12—C13—H13	120.00	H32A—C32—H32B	109.00
H14A—C14—H14B	109.00	H32B—C32—H32C	109.00
H14A—C14—H14C	109.00	C36—C35—H35	122.00
C11—C14—H14A	109.00	C34—C35—H35	122.00
C11—C14—H14B	109.00	C36—C37—H37	121.00
C11—C14—H14C	109.00	C38—C37—H37	121.00
H14B—C14—H14C	109.00	C37—C38—H38	119.00
C18—C17—H17	121.00	C33—C38—H38	119.00
C5—N1—C2—N3	−0.12 (17)	C14—C11—C12—C13	−179.34 (18)
C5—N1—C2—C15	−178.94 (14)	C10—C11—C12—C13	0.5 (3)
C8—N1—C2—N3	−166.06 (13)	C11—C12—C13—C8	−0.1 (3)
C8—N1—C2—C15	15.1 (2)	C2—C15—C16—C17	177.59 (17)
C2—N1—C5—C4	−0.17 (16)	C20—C15—C16—F1	−177.42 (14)
C2—N1—C5—C6	−179.31 (14)	C2—C15—C16—F1	−0.5 (2)
C8—N1—C5—C4	165.92 (13)	C2—C15—C20—C19	−177.35 (14)
C8—N1—C5—C6	−13.2 (2)	C16—C15—C20—C19	−0.3 (2)
C2—N1—C8—C9	52.4 (2)	C20—C15—C16—C17	0.7 (2)
C2—N1—C8—C13	−128.40 (17)	C15—C16—C17—C18	−0.4 (3)
C5—N1—C8—C9	−111.13 (17)	F1—C16—C17—C18	177.69 (17)
C5—N1—C8—C13	68.1 (2)	C16—C17—C18—F2	−179.81 (17)
C4—N3—C2—N1	0.34 (17)	C16—C17—C18—C19	−0.2 (3)
C4—N3—C2—C15	179.16 (14)	C17—C18—C19—C20	0.5 (3)
C2—N3—C4—C5	−0.45 (17)	F2—C18—C19—C20	−179.88 (15)
C2—N3—C4—C7	−179.74 (14)	C18—C19—C20—C15	−0.2 (2)
C23—N4—C21—N5	−0.03 (17)	N4—C21—C33—C34	−47.0 (2)
C23—N4—C21—C33	178.51 (14)	N4—C21—C33—C38	136.58 (16)
C26—N4—C21—N5	166.26 (14)	N5—C21—C33—C34	131.35 (17)
C26—N4—C21—C33	−15.2 (2)	N5—C21—C33—C38	−45.1 (2)
C21—N4—C23—C22	0.31 (17)	N5—C22—C23—N4	−0.49 (18)
C21—N4—C23—C24	179.64 (15)	N5—C22—C23—C24	−179.73 (16)
C26—N4—C23—C22	−166.13 (14)	C25—C22—C23—N4	−179.64 (16)
C26—N4—C23—C24	13.2 (2)	C25—C22—C23—C24	1.1 (3)
C21—N4—C26—C27	126.12 (17)	N4—C26—C27—C28	179.68 (14)
C21—N4—C26—C31	−53.9 (2)	C31—C26—C27—C28	−0.3 (2)
C23—N4—C26—C27	−70.0 (2)	N4—C26—C31—C30	−179.73 (14)
C23—N4—C26—C31	110.01 (17)	C27—C26—C31—C30	0.3 (2)
C22—N5—C21—N4	−0.27 (17)	C26—C27—C28—C29	0.2 (2)
C22—N5—C21—C33	−178.81 (14)	C27—C28—C29—C30	0.1 (3)
C21—N5—C22—C23	0.48 (18)	C27—C28—C29—C32	−179.77 (17)
C21—N5—C22—C25	179.72 (15)	C28—C29—C30—C31	−0.1 (3)
N1—C2—C15—C16	48.6 (2)	C32—C29—C30—C31	179.72 (17)
N1—C2—C15—C20	−134.62 (16)	C29—C30—C31—C26	−0.1 (3)
N3—C2—C15—C16	−130.11 (17)	C21—C33—C34—F3	0.0 (2)
N3—C2—C15—C20	46.7 (2)	C21—C33—C34—C35	−178.20 (17)
N3—C4—C5—N1	0.38 (17)	C38—C33—C34—F3	176.57 (15)
N3—C4—C5—C6	179.41 (16)	C38—C33—C34—C35	−1.6 (3)
C7—C4—C5—N1	179.59 (15)	C21—C33—C38—C37	177.67 (15)
C7—C4—C5—C6	−1.4 (3)	C34—C33—C38—C37	1.0 (2)
N1—C8—C9—C10	−179.85 (14)	F3—C34—C35—C36	−177.02 (17)
C13—C8—C9—C10	0.9 (2)	C33—C34—C35—C36	1.2 (3)
N1—C8—C13—C12	−179.83 (15)	C34—C35—C36—F4	179.56 (17)
C9—C8—C13—C12	−0.6 (2)	C34—C35—C36—C37	−0.1 (3)
C8—C9—C10—C11	−0.5 (3)	F4—C36—C37—C38	179.88 (15)
C9—C10—C11—C12	−0.1 (3)	C35—C36—C37—C38	−0.5 (3)
C9—C10—C11—C14	179.66 (18)	C36—C37—C38—C33	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N5i	0.82 (3)	2.17 (3)	2.987 (2)	177 (2)
O1W—H1WB···O1Wii	0.72 (2)	2.42 (2)	2.894 (3)	125 (2)
O2W—H2WA···N3	0.84 (3)	2.16 (3)	2.995 (2)	174 (2)
O2W—H2WB···O2Wiii	0.73 (2)	2.42 (2)	2.910 (2)	126 (2)
C17—H17···F3iv	0.93	2.46	3.253 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯N5i	0.82 (3)	2.17 (3)	2.987 (2)	177 (2)
O1W—H1WB⋯O1W ii	0.72 (2)	2.42 (2)	2.894 (3)	125 (2)
O2W—H2WA⋯N3	0.84 (3)	2.16 (3)	2.995 (2)	174 (2)
O2W—H2WB⋯O2W iii	0.73 (2)	2.42 (2)	2.910 (2)	126 (2)
C17—H17⋯F3iv	0.93	2.46	3.253 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .