Structures and biological activity of three 2-(pyridin-2-yl)-1H-benz­imid­a­zole derivatives

Two new 2-(pyridin-2-yl)-1H-benz­imid­a­zole derivatives, namely, 2-(4-phen­oxy­pyridin-2-yl)-1H-benz­imid­a­zole, C₁₈H₁₃N₃O, and 2-[4-(4-fluoro­phen­oxy)py­ri­din-2-yl]-1H-benz­imid­a­zole, C₁₈H₁₂FN₃O, were synthesized and characterized by NMR spectroscopy. Crystal structure, biological activity and ADME analyses were performed for these two new compounds and a third compound, namely, 5,6-dimethyl-2-[4-(4-phenyl­piperazin-1-yl)pyridin-2-yl]-1H-benz­imid­a­zole me­thanol monosolvate, C₂₄H₂₅N₅·CH₃OH, the synthesis of which had been described previously. All three compounds have a similar chain hydrogen-bonding pattern. One of them (the fluoro­phen­oxy derivative) showed good anti­microbial activity against Gram-positive bacteria. The ADME analysis indicates that the com­pounds could be good drug candidates.

Computing details

5,6-Dimethyl-2-[4-(4-phenylpiperazin-1-yl)pyridin-2-yl]-1H-1,3-benzodiazole methanol monosolvate (B1)

Crystal data

C24H25N5·CH4O	Dx = 1.270 Mg m^−3
Mr = 415.53	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 11676 reflections
a = 11.20036 (16) Å	θ = 3.1–79.1°
b = 13.57837 (16) Å	µ = 0.63 mm^−1
c = 28.5899 (4) Å	T = 100 K
V = 4348.02 (11) Å^3	Plate, clear light colourless
Z = 8	0.19 × 0.08 × 0.03 mm
F(000) = 1776

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector	4049 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3496 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 5.8140 pixels mm^-1	θmax = 70.1°, θmin = 3.1°
ω scans	h = −13→10
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2023)	k = −13→16
Tmin = 0.857, Tmax = 1.000	l = −33→33
23230 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.1033P)^2 + 1.240P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4049 reflections	Δρmax = 0.32 e Å^−3
296 parameters	Δρmin = −0.32 e Å^−3
1 restraint

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1M	0.5200 (2)	0.57861 (16)	0.61031 (8)	0.0494 (5)
H1MA	0.562801	0.546923	0.584481	0.074*
H1MB	0.526328	0.537642	0.638423	0.074*
H1MC	0.555093	0.643431	0.616470	0.074*
O1MA	0.3996 (2)	0.58978 (18)	0.59826 (18)	0.0344 (11)	0.83 (2)
H1MD	0.374162	0.643583	0.608777	0.052*	0.83 (2)
O1MB	0.3986 (13)	0.5878 (13)	0.6192 (18)	0.081 (7)	0.17 (2)
H1ME	0.359727	0.561122	0.597490	0.121*	0.17 (2)
C1	0.23333 (15)	0.82852 (11)	0.60082 (6)	0.0294 (4)
C8	0.16015 (14)	0.80278 (12)	0.55966 (6)	0.0289 (4)
C9	0.17085 (14)	0.71156 (11)	0.53816 (6)	0.0290 (4)
H9	0.225601	0.664146	0.549863	0.035*
C10	0.09960 (15)	0.68989 (11)	0.49874 (6)	0.0292 (4)
C11	0.02274 (15)	0.76575 (12)	0.48393 (6)	0.0315 (4)
H11	−0.027845	0.756070	0.457660	0.038*
C12	0.02107 (15)	0.85440 (12)	0.50773 (6)	0.0319 (4)
H12	−0.030918	0.904274	0.496395	0.038*
C13	0.04878 (16)	0.59590 (12)	0.42951 (6)	0.0347 (4)
H13A	0.094974	0.639147	0.408302	0.042*
H13B	−0.033641	0.621999	0.431172	0.042*
C14	0.04518 (16)	0.49298 (12)	0.40899 (6)	0.0343 (4)
H14A	−0.016612	0.453772	0.425311	0.041*
H14B	0.023035	0.496843	0.375515	0.041*
C15	0.18686 (15)	0.43351 (12)	0.46320 (6)	0.0309 (4)
H15A	0.260190	0.393809	0.467486	0.037*
H15B	0.120128	0.399033	0.478935	0.037*
C16	0.20391 (15)	0.53467 (12)	0.48481 (6)	0.0311 (4)
H16A	0.215632	0.527376	0.518952	0.037*
H16B	0.276896	0.565113	0.471668	0.037*
C17	0.16929 (15)	0.35700 (12)	0.38560 (6)	0.0323 (4)
C18	0.17338 (18)	0.36791 (14)	0.33705 (7)	0.0413 (4)
H18	0.169512	0.431883	0.323682	0.050*
C19	0.18303 (19)	0.28624 (16)	0.30815 (7)	0.0467 (5)
H19	0.186354	0.294812	0.275200	0.056*
C20	0.18785 (18)	0.19260 (15)	0.32687 (7)	0.0446 (5)
H20	0.194027	0.136746	0.307011	0.053*
C21	0.18358 (18)	0.18118 (14)	0.37473 (7)	0.0433 (5)
H21	0.186888	0.116916	0.387808	0.052*
C22	0.17451 (16)	0.26239 (13)	0.40419 (7)	0.0378 (4)
H22	0.171871	0.253219	0.437111	0.045*
C23	0.4544 (2)	1.05835 (16)	0.75573 (8)	0.0523 (5)
H23A	0.541261	1.067037	0.755820	0.079*
H23B	0.427627	1.039154	0.787062	0.079*
H23C	0.415969	1.120383	0.746763	0.079*
C24	0.5734 (2)	0.86619 (17)	0.75888 (7)	0.0502 (5)
H24A	0.603738	0.798938	0.755149	0.075*
H24B	0.539620	0.873923	0.790277	0.075*
H24C	0.639003	0.913146	0.754635	0.075*
C2	0.30412 (15)	0.92373 (12)	0.65653 (6)	0.0318 (4)
C3	0.33442 (17)	0.99862 (13)	0.68789 (7)	0.0373 (4)
H3	0.296739	1.061228	0.686469	0.045*
C4	0.42092 (18)	0.97872 (14)	0.72101 (6)	0.0398 (4)
C5	0.47811 (17)	0.88550 (14)	0.72287 (6)	0.0398 (4)
C6	0.44685 (17)	0.81147 (13)	0.69134 (6)	0.0363 (4)
H6	0.485036	0.749039	0.692383	0.044*
C7	0.35823 (15)	0.83094 (12)	0.65815 (6)	0.0310 (4)
N1	0.22564 (14)	0.92042 (10)	0.61954 (5)	0.0316 (3)
H1	0.177 (2)	0.9682 (18)	0.6109 (9)	0.047*
N2	0.31218 (13)	0.77188 (10)	0.62247 (5)	0.0303 (3)
N3	0.08691 (12)	0.87540 (10)	0.54543 (5)	0.0320 (3)
N4	0.10225 (12)	0.59985 (10)	0.47632 (5)	0.0302 (3)
N5	0.16097 (12)	0.44378 (10)	0.41354 (5)	0.0314 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1M	0.0539 (13)	0.0464 (11)	0.0478 (12)	0.0031 (9)	−0.0029 (9)	0.0039 (9)
O1MA	0.0373 (14)	0.0239 (9)	0.0420 (19)	−0.0009 (7)	0.0055 (8)	−0.0037 (9)
O1MB	0.106 (12)	0.045 (6)	0.092 (19)	−0.001 (6)	0.056 (10)	−0.011 (9)
C1	0.0317 (8)	0.0242 (7)	0.0323 (9)	−0.0037 (6)	0.0049 (7)	−0.0017 (6)
C8	0.0281 (8)	0.0263 (7)	0.0322 (9)	−0.0018 (6)	0.0036 (6)	0.0014 (6)
C9	0.0295 (8)	0.0251 (7)	0.0325 (9)	−0.0008 (6)	0.0000 (6)	0.0016 (6)
C10	0.0285 (8)	0.0249 (8)	0.0341 (9)	−0.0021 (6)	0.0015 (7)	0.0009 (6)
C11	0.0296 (8)	0.0294 (8)	0.0356 (9)	−0.0005 (6)	−0.0013 (7)	0.0007 (6)
C12	0.0287 (8)	0.0288 (8)	0.0383 (10)	0.0027 (6)	0.0022 (7)	0.0026 (6)
C13	0.0355 (9)	0.0316 (8)	0.0369 (10)	0.0049 (7)	−0.0072 (7)	−0.0020 (7)
C14	0.0354 (9)	0.0324 (9)	0.0351 (9)	0.0031 (7)	−0.0074 (7)	−0.0029 (7)
C15	0.0312 (8)	0.0275 (8)	0.0339 (9)	0.0014 (6)	−0.0038 (7)	0.0004 (6)
C16	0.0314 (8)	0.0290 (8)	0.0331 (9)	0.0013 (6)	−0.0053 (7)	−0.0016 (6)
C17	0.0275 (8)	0.0310 (8)	0.0383 (10)	0.0000 (6)	−0.0032 (7)	−0.0036 (7)
C18	0.0505 (11)	0.0358 (9)	0.0375 (10)	0.0052 (8)	−0.0033 (8)	−0.0003 (8)
C19	0.0559 (12)	0.0476 (11)	0.0365 (10)	0.0080 (9)	−0.0036 (9)	−0.0069 (8)
C20	0.0473 (11)	0.0397 (10)	0.0466 (12)	0.0049 (8)	−0.0054 (9)	−0.0138 (8)
C21	0.0486 (11)	0.0308 (9)	0.0506 (12)	−0.0004 (8)	−0.0048 (9)	−0.0025 (8)
C22	0.0409 (10)	0.0322 (9)	0.0402 (10)	−0.0015 (7)	−0.0016 (8)	−0.0008 (7)
C23	0.0638 (13)	0.0518 (12)	0.0414 (11)	−0.0153 (10)	0.0020 (10)	−0.0157 (9)
C24	0.0527 (12)	0.0585 (12)	0.0394 (11)	−0.0110 (10)	−0.0063 (9)	−0.0066 (9)
C2	0.0350 (9)	0.0301 (8)	0.0304 (9)	−0.0060 (7)	0.0067 (7)	−0.0015 (6)
C3	0.0436 (10)	0.0303 (8)	0.0380 (10)	−0.0067 (7)	0.0097 (8)	−0.0075 (7)
C4	0.0476 (11)	0.0398 (9)	0.0319 (10)	−0.0146 (8)	0.0083 (8)	−0.0082 (7)
C5	0.0421 (10)	0.0452 (10)	0.0320 (9)	−0.0123 (8)	0.0010 (7)	−0.0019 (8)
C6	0.0420 (10)	0.0335 (9)	0.0334 (9)	−0.0057 (7)	−0.0006 (7)	0.0000 (7)
C7	0.0360 (9)	0.0284 (8)	0.0286 (9)	−0.0068 (6)	0.0024 (7)	−0.0020 (6)
N1	0.0343 (8)	0.0256 (7)	0.0350 (8)	−0.0010 (6)	0.0029 (6)	−0.0026 (6)
N2	0.0341 (7)	0.0253 (6)	0.0314 (7)	−0.0035 (5)	−0.0007 (6)	−0.0016 (5)
N3	0.0317 (7)	0.0271 (6)	0.0372 (8)	−0.0003 (5)	0.0031 (6)	−0.0006 (6)
N4	0.0311 (7)	0.0256 (6)	0.0339 (8)	0.0014 (5)	−0.0057 (6)	−0.0016 (5)
N5	0.0323 (7)	0.0289 (7)	0.0330 (8)	0.0027 (5)	−0.0043 (6)	−0.0022 (6)

Geometric parameters (Å, º)

C1M—H1MA	0.9800	C16—N4	1.462 (2)
C1M—H1MB	0.9800	C17—C18	1.397 (3)
C1M—H1MC	0.9800	C17—C22	1.391 (2)
C1M—O1MA	1.399 (3)	C17—N5	1.427 (2)
C1M—O1MB	1.389 (9)	C18—H18	0.9500
O1MA—H1MD	0.8400	C18—C19	1.387 (3)
O1MB—H1ME	0.8400	C19—H19	0.9500
C1—C8	1.476 (2)	C19—C20	1.381 (3)
C1—N1	1.360 (2)	C20—H20	0.9500
C1—N2	1.325 (2)	C20—C21	1.378 (3)
C8—C9	1.388 (2)	C21—H21	0.9500
C8—N3	1.346 (2)	C21—C22	1.391 (3)
C9—H9	0.9500	C22—H22	0.9500
C9—C10	1.412 (2)	C23—H23A	0.9800
C10—C11	1.408 (2)	C23—H23B	0.9800
C10—N4	1.381 (2)	C23—H23C	0.9800
C11—H11	0.9500	C23—C4	1.515 (2)
C11—C12	1.383 (2)	C24—H24A	0.9800
C12—H12	0.9500	C24—H24B	0.9800
C12—N3	1.337 (2)	C24—H24C	0.9800
C13—H13A	0.9900	C24—C5	1.506 (3)
C13—H13B	0.9900	C2—C3	1.397 (2)
C13—C14	1.516 (2)	C2—C7	1.399 (2)
C13—N4	1.467 (2)	C2—N1	1.376 (2)
C14—H14A	0.9900	C3—H3	0.9500
C14—H14B	0.9900	C3—C4	1.381 (3)
C14—N5	1.465 (2)	C4—C5	1.420 (3)
C15—H15A	0.9900	C5—C6	1.395 (3)
C15—H15B	0.9900	C6—H6	0.9500
C15—C16	1.518 (2)	C6—C7	1.398 (3)
C15—N5	1.456 (2)	C7—N2	1.396 (2)
C16—H16A	0.9900	N1—H1	0.88 (3)
C16—H16B	0.9900
H1MA—C1M—H1MB	109.5	C19—C18—H18	119.7
H1MA—C1M—H1MC	109.5	C18—C19—H19	119.7
H1MB—C1M—H1MC	109.5	C20—C19—C18	120.56 (19)
O1MA—C1M—H1MA	109.5	C20—C19—H19	119.7
O1MA—C1M—H1MB	109.5	C19—C20—H20	120.4
O1MA—C1M—H1MC	109.5	C21—C20—C19	119.16 (18)
C1M—O1MA—H1MD	109.5	C21—C20—H20	120.4
C1M—O1MB—H1ME	109.5	C20—C21—H21	119.5
N1—C1—C8	119.70 (15)	C20—C21—C22	120.95 (18)
N2—C1—C8	127.25 (14)	C22—C21—H21	119.5
N2—C1—N1	113.02 (15)	C17—C22—H22	119.9
C9—C8—C1	121.09 (15)	C21—C22—C17	120.25 (18)
N3—C8—C1	113.95 (14)	C21—C22—H22	119.9
N3—C8—C9	124.95 (16)	H23A—C23—H23B	109.5
C8—C9—H9	120.3	H23A—C23—H23C	109.5
C8—C9—C10	119.38 (15)	H23B—C23—H23C	109.5
C10—C9—H9	120.3	C4—C23—H23A	109.5
C11—C10—C9	115.67 (15)	C4—C23—H23B	109.5
N4—C10—C9	122.89 (15)	C4—C23—H23C	109.5
N4—C10—C11	121.43 (15)	H24A—C24—H24B	109.5
C10—C11—H11	120.1	H24A—C24—H24C	109.5
C12—C11—C10	119.83 (16)	H24B—C24—H24C	109.5
C12—C11—H11	120.1	C5—C24—H24A	109.5
C11—C12—H12	117.5	C5—C24—H24B	109.5
N3—C12—C11	125.09 (15)	C5—C24—H24C	109.5
N3—C12—H12	117.5	C3—C2—C7	121.93 (17)
H13A—C13—H13B	107.7	N1—C2—C3	132.22 (16)
C14—C13—H13A	108.9	N1—C2—C7	105.83 (14)
C14—C13—H13B	108.9	C2—C3—H3	121.1
N4—C13—H13A	108.9	C4—C3—C2	117.89 (17)
N4—C13—H13B	108.9	C4—C3—H3	121.1
N4—C13—C14	113.43 (14)	C3—C4—C23	118.89 (19)
C13—C14—H14A	109.4	C3—C4—C5	121.11 (16)
C13—C14—H14B	109.4	C5—C4—C23	120.01 (19)
H14A—C14—H14B	108.0	C4—C5—C24	120.05 (17)
N5—C14—C13	111.25 (14)	C6—C5—C24	119.62 (18)
N5—C14—H14A	109.4	C6—C5—C4	120.33 (18)
N5—C14—H14B	109.4	C5—C6—H6	120.6
H15A—C15—H15B	108.2	C5—C6—C7	118.72 (17)
C16—C15—H15A	109.8	C7—C6—H6	120.6
C16—C15—H15B	109.8	C6—C7—C2	120.02 (16)
N5—C15—H15A	109.8	N2—C7—C2	109.45 (15)
N5—C15—H15B	109.8	N2—C7—C6	130.49 (16)
N5—C15—C16	109.58 (13)	C1—N1—C2	106.97 (14)
C15—C16—H16A	109.1	C1—N1—H1	127.0 (16)
C15—C16—H16B	109.1	C2—N1—H1	125.9 (16)
H16A—C16—H16B	107.8	C1—N2—C7	104.72 (14)
N4—C16—C15	112.47 (13)	C12—N3—C8	115.07 (14)
N4—C16—H16A	109.1	C10—N4—C13	116.56 (13)
N4—C16—H16B	109.1	C10—N4—C16	118.40 (13)
C18—C17—N5	118.10 (16)	C16—N4—C13	116.54 (13)
C22—C17—C18	118.42 (17)	C15—N5—C14	107.86 (13)
C22—C17—N5	123.47 (17)	C17—N5—C14	112.63 (13)
C17—C18—H18	119.7	C17—N5—C15	117.00 (13)
C19—C18—C17	120.65 (18)
C1—C8—C9—C10	−179.75 (15)	C23—C4—C5—C24	−0.9 (3)
C1—C8—N3—C12	178.97 (14)	C23—C4—C5—C6	179.32 (18)
C8—C1—N1—C2	−179.07 (14)	C24—C5—C6—C7	−179.93 (17)
C8—C1—N2—C7	178.71 (16)	C2—C3—C4—C23	−179.36 (17)
C8—C9—C10—C11	0.8 (2)	C2—C3—C4—C5	0.6 (3)
C8—C9—C10—N4	−177.91 (15)	C2—C7—N2—C1	−0.20 (18)
C9—C8—N3—C12	0.2 (2)	C3—C2—C7—C6	−1.1 (3)
C9—C10—C11—C12	0.1 (2)	C3—C2—C7—N2	−179.08 (15)
C9—C10—N4—C13	−164.45 (16)	C3—C2—N1—C1	179.26 (18)
C9—C10—N4—C16	−17.5 (2)	C3—C4—C5—C24	179.09 (18)
C10—C11—C12—N3	−1.1 (3)	C3—C4—C5—C6	−0.6 (3)
C11—C10—N4—C13	16.9 (2)	C4—C5—C6—C7	−0.2 (3)
C11—C10—N4—C16	163.83 (15)	C5—C6—C7—C2	1.0 (3)
C11—C12—N3—C8	0.9 (2)	C5—C6—C7—N2	178.54 (17)
C13—C14—N5—C15	62.80 (18)	C6—C7—N2—C1	−177.91 (18)
C13—C14—N5—C17	−166.58 (15)	C7—C2—C3—C4	0.3 (3)
C14—C13—N4—C10	−174.85 (15)	C7—C2—N1—C1	0.64 (18)
C14—C13—N4—C16	37.6 (2)	N1—C1—C8—C9	176.35 (15)
C15—C16—N4—C10	172.30 (14)	N1—C1—C8—N3	−2.4 (2)
C15—C16—N4—C13	−40.7 (2)	N1—C1—N2—C7	0.63 (19)
C16—C15—N5—C14	−65.78 (17)	N1—C2—C3—C4	−178.19 (18)
C16—C15—N5—C17	166.06 (14)	N1—C2—C7—C6	177.71 (15)
C17—C18—C19—C20	0.5 (3)	N1—C2—C7—N2	−0.28 (19)
C18—C17—C22—C21	0.0 (3)	N2—C1—C8—C9	−1.6 (3)
C18—C17—N5—C14	69.2 (2)	N2—C1—C8—N3	179.60 (15)
C18—C17—N5—C15	−164.96 (16)	N2—C1—N1—C2	−0.82 (19)
C18—C19—C20—C21	−0.3 (3)	N3—C8—C9—C10	−1.1 (3)
C19—C20—C21—C22	0.0 (3)	N4—C10—C11—C12	178.91 (15)
C20—C21—C22—C17	0.2 (3)	N4—C13—C14—N5	−48.2 (2)
C22—C17—C18—C19	−0.3 (3)	N5—C15—C16—N4	54.72 (19)
C22—C17—N5—C14	−111.33 (19)	N5—C17—C18—C19	179.16 (17)
C22—C17—N5—C15	14.5 (2)	N5—C17—C22—C21	−179.45 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1MA—H1MD···N2	0.84	1.92	2.748 (3)	171
O1MB—H1ME···N1^i	0.84	2.23	2.665 (16)	113
C9—H9···O1MA	0.95	2.59	3.500 (3)	160
N1—H1···O1MA^ii	0.88 (3)	1.90 (3)	2.762 (3)	167 (2)
N1—H1···O1MB^ii	0.88 (3)	1.85 (3)	2.665 (16)	153 (3)

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

2-(4-Phenoxypyridin-2-yl)-1H-1,3-benzodiazole (B2)

Crystal data

C18H13N3O	F(000) = 600
Mr = 287.31	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.0255 (3) Å	Cell parameters from 7686 reflections
b = 13.8022 (3) Å	θ = 4.5–77.1°
c = 10.1885 (3) Å	µ = 0.70 mm^−1
β = 115.648 (3)°	T = 100 K
V = 1397.68 (7) Å^3	Plate, clear light colourless
Z = 4	0.60 × 0.14 × 0.02 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector	2824 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2502 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
Detector resolution: 5.8140 pixels mm^-1	θmax = 78.3°, θmin = 4.5°
ω scans	h = −13→12
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2023)	k = −17→16
Tmin = 0.512, Tmax = 1.000	l = −12→12
17391 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0742P)^2 + 0.3403P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2824 reflections	Δρmax = 0.26 e Å^−3
202 parameters	Δρmin = −0.31 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.64883 (11)	0.73729 (8)	0.40006 (11)	0.0223 (3)
H1	0.6202 (17)	0.7237 (13)	0.301 (2)	0.033*
O1	0.22642 (10)	0.52750 (8)	0.53489 (10)	0.0287 (3)
N2	0.63390 (11)	0.75725 (8)	0.61109 (11)	0.0220 (3)
N3	0.43977 (12)	0.60524 (9)	0.29906 (12)	0.0247 (3)
C1	0.58107 (13)	0.71534 (10)	0.48093 (13)	0.0211 (3)
C2	0.75451 (13)	0.79656 (10)	0.48359 (13)	0.0221 (3)
C3	0.85979 (14)	0.83712 (10)	0.46105 (14)	0.0244 (3)
H3	0.867645	0.827246	0.372768	0.029*
C4	0.95190 (14)	0.89212 (10)	0.57237 (15)	0.0257 (3)
H4	1.025239	0.920424	0.560831	0.031*
C5	0.93984 (14)	0.90745 (10)	0.70341 (15)	0.0259 (3)
H5	1.004068	0.946980	0.777085	0.031*
C6	0.83686 (14)	0.86623 (10)	0.72650 (14)	0.0238 (3)
H6	0.829673	0.876315	0.815100	0.029*
C7	0.74328 (13)	0.80911 (10)	0.61546 (13)	0.0215 (3)
C8	0.46862 (13)	0.64688 (10)	0.42880 (13)	0.0214 (3)
C9	0.40202 (13)	0.62599 (10)	0.51510 (14)	0.0229 (3)
H9	0.424323	0.658615	0.604711	0.028*
C10	0.30257 (14)	0.55611 (10)	0.46519 (14)	0.0233 (3)
C11	0.27382 (14)	0.50946 (10)	0.33357 (15)	0.0244 (3)
H11	0.208134	0.459552	0.298685	0.029*
C12	0.34340 (14)	0.53777 (11)	0.25538 (14)	0.0256 (3)
H12	0.321264	0.507197	0.164304	0.031*
C13	0.23766 (14)	0.57783 (10)	0.65961 (14)	0.0255 (3)
C14	0.13158 (16)	0.63543 (11)	0.64702 (16)	0.0323 (3)
H14	0.058650	0.646814	0.554599	0.039*
C15	0.13298 (18)	0.67696 (12)	0.77272 (18)	0.0375 (4)
H15	0.060176	0.716542	0.766473	0.045*
C16	0.24039 (18)	0.66039 (11)	0.90613 (17)	0.0354 (4)
H16	0.240724	0.688051	0.991668	0.043*
C17	0.34768 (16)	0.60362 (11)	0.91587 (15)	0.0325 (4)
H17	0.422153	0.593764	1.007659	0.039*
C18	0.34662 (15)	0.56110 (11)	0.79179 (15)	0.0282 (3)
H18	0.419187	0.521393	0.797678	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0268 (6)	0.0282 (6)	0.0140 (5)	−0.0003 (5)	0.0108 (4)	0.0001 (4)
O1	0.0338 (6)	0.0363 (6)	0.0224 (5)	−0.0103 (4)	0.0183 (4)	−0.0068 (4)
N2	0.0255 (6)	0.0269 (6)	0.0146 (5)	0.0004 (5)	0.0097 (4)	−0.0002 (4)
N3	0.0274 (6)	0.0315 (6)	0.0159 (5)	0.0005 (5)	0.0102 (4)	−0.0018 (4)
C1	0.0244 (7)	0.0265 (7)	0.0148 (5)	0.0031 (5)	0.0107 (5)	0.0019 (5)
C2	0.0281 (7)	0.0231 (7)	0.0165 (6)	0.0029 (5)	0.0111 (5)	0.0026 (5)
C3	0.0297 (7)	0.0271 (7)	0.0194 (6)	0.0024 (5)	0.0133 (5)	0.0051 (5)
C4	0.0282 (7)	0.0247 (7)	0.0265 (7)	0.0002 (6)	0.0141 (6)	0.0043 (5)
C5	0.0287 (7)	0.0240 (7)	0.0235 (7)	−0.0001 (5)	0.0097 (6)	0.0001 (5)
C6	0.0283 (7)	0.0250 (7)	0.0188 (6)	0.0020 (5)	0.0107 (5)	−0.0005 (5)
C7	0.0254 (7)	0.0239 (6)	0.0169 (6)	0.0031 (5)	0.0108 (5)	0.0025 (5)
C8	0.0246 (7)	0.0256 (7)	0.0148 (6)	0.0034 (5)	0.0093 (5)	0.0018 (5)
C9	0.0265 (7)	0.0275 (7)	0.0160 (6)	0.0012 (5)	0.0102 (5)	0.0002 (5)
C10	0.0256 (7)	0.0274 (7)	0.0190 (6)	0.0027 (5)	0.0118 (5)	0.0034 (5)
C11	0.0248 (7)	0.0257 (7)	0.0219 (6)	−0.0004 (5)	0.0094 (5)	−0.0017 (5)
C12	0.0272 (7)	0.0323 (7)	0.0173 (6)	0.0004 (6)	0.0097 (5)	−0.0042 (5)
C13	0.0333 (8)	0.0278 (7)	0.0209 (6)	−0.0061 (6)	0.0168 (6)	−0.0014 (5)
C14	0.0375 (8)	0.0348 (8)	0.0265 (7)	0.0045 (7)	0.0157 (6)	0.0075 (6)
C15	0.0527 (10)	0.0308 (8)	0.0413 (9)	0.0087 (7)	0.0317 (8)	0.0052 (7)
C16	0.0579 (10)	0.0286 (8)	0.0300 (7)	−0.0085 (7)	0.0286 (7)	−0.0050 (6)
C17	0.0393 (9)	0.0371 (8)	0.0216 (7)	−0.0114 (7)	0.0139 (6)	−0.0013 (6)
C18	0.0290 (7)	0.0327 (8)	0.0268 (7)	−0.0027 (6)	0.0156 (6)	0.0014 (6)

Geometric parameters (Å, º)

N1—H1	0.938 (19)	C6—C7	1.3984 (19)
N1—C1	1.3644 (16)	C8—C9	1.3980 (17)
N1—C2	1.3758 (18)	C9—H9	0.9500
O1—C10	1.3716 (16)	C9—C10	1.381 (2)
O1—C13	1.4058 (16)	C10—C11	1.3948 (19)
N2—C1	1.3281 (16)	C11—H11	0.9500
N2—C7	1.3864 (17)	C11—C12	1.3801 (19)
N3—C8	1.3471 (16)	C12—H12	0.9500
N3—C12	1.3360 (19)	C13—C14	1.373 (2)
C1—C8	1.4635 (19)	C13—C18	1.382 (2)
C2—C3	1.3944 (19)	C14—H14	0.9500
C2—C7	1.4122 (17)	C14—C15	1.397 (2)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.377 (2)	C15—C16	1.382 (2)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.4136 (19)	C16—C17	1.386 (2)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.378 (2)	C17—C18	1.389 (2)
C6—H6	0.9500	C18—H18	0.9500
C1—N1—H1	126.1 (11)	C8—C9—H9	121.2
C1—N1—C2	107.28 (10)	C10—C9—C8	117.50 (12)
C2—N1—H1	125.8 (11)	C10—C9—H9	121.2
C10—O1—C13	119.44 (11)	O1—C10—C9	125.21 (12)
C1—N2—C7	104.86 (10)	O1—C10—C11	115.45 (12)
C12—N3—C8	116.13 (11)	C9—C10—C11	119.34 (12)
N1—C1—C8	121.56 (11)	C10—C11—H11	120.9
N2—C1—N1	112.83 (12)	C12—C11—C10	118.20 (13)
N2—C1—C8	125.46 (11)	C12—C11—H11	120.9
N1—C2—C3	132.80 (12)	N3—C12—C11	124.44 (12)
N1—C2—C7	105.18 (11)	N3—C12—H12	117.8
C3—C2—C7	121.97 (12)	C11—C12—H12	117.8
C2—C3—H3	121.5	C14—C13—O1	117.60 (13)
C4—C3—C2	117.09 (12)	C14—C13—C18	122.25 (13)
C4—C3—H3	121.5	C18—C13—O1	119.84 (13)
C3—C4—H4	119.2	C13—C14—H14	120.6
C3—C4—C5	121.53 (13)	C13—C14—C15	118.74 (14)
C5—C4—H4	119.2	C15—C14—H14	120.6
C4—C5—H5	119.3	C14—C15—H15	120.0
C6—C5—C4	121.38 (13)	C16—C15—C14	119.90 (15)
C6—C5—H5	119.3	C16—C15—H15	120.0
C5—C6—H6	121.0	C15—C16—H16	119.8
C5—C6—C7	117.94 (12)	C15—C16—C17	120.37 (14)
C7—C6—H6	121.0	C17—C16—H16	119.8
N2—C7—C2	109.84 (11)	C16—C17—H17	119.9
N2—C7—C6	130.09 (11)	C16—C17—C18	120.19 (14)
C6—C7—C2	120.07 (12)	C18—C17—H17	119.9
N3—C8—C1	115.77 (11)	C13—C18—C17	118.53 (14)
N3—C8—C9	124.32 (13)	C13—C18—H18	120.7
C9—C8—C1	119.87 (11)	C17—C18—H18	120.7
N1—C1—C8—N3	2.00 (19)	C5—C6—C7—N2	177.72 (13)
N1—C1—C8—C9	179.76 (12)	C5—C6—C7—C2	−1.16 (19)
N1—C2—C3—C4	−178.25 (13)	C7—N2—C1—N1	−0.42 (15)
N1—C2—C7—N2	0.73 (15)	C7—N2—C1—C8	175.31 (12)
N1—C2—C7—C6	179.83 (12)	C7—C2—C3—C4	−1.3 (2)
O1—C10—C11—C12	177.50 (12)	C8—N3—C12—C11	0.1 (2)
O1—C13—C14—C15	172.41 (13)	C8—C9—C10—O1	−179.23 (12)
O1—C13—C18—C17	−172.98 (12)	C8—C9—C10—C11	0.5 (2)
N2—C1—C8—N3	−173.38 (12)	C9—C10—C11—C12	−2.3 (2)
N2—C1—C8—C9	4.4 (2)	C10—O1—C13—C14	108.48 (15)
N3—C8—C9—C10	1.8 (2)	C10—O1—C13—C18	−77.72 (17)
C1—N1—C2—C3	176.37 (14)	C10—C11—C12—N3	2.0 (2)
C1—N1—C2—C7	−0.95 (14)	C12—N3—C8—C1	175.56 (12)
C1—N2—C7—C2	−0.21 (14)	C12—N3—C8—C9	−2.1 (2)
C1—N2—C7—C6	−179.19 (14)	C13—O1—C10—C9	6.8 (2)
C1—C8—C9—C10	−175.78 (12)	C13—O1—C10—C11	−172.94 (12)
C2—N1—C1—N2	0.90 (15)	C13—C14—C15—C16	0.6 (2)
C2—N1—C1—C8	−175.02 (11)	C14—C13—C18—C17	0.5 (2)
C2—C3—C4—C5	−0.4 (2)	C14—C15—C16—C17	0.7 (2)
C3—C2—C7—N2	−176.95 (12)	C15—C16—C17—C18	−1.5 (2)
C3—C2—C7—C6	2.1 (2)	C16—C17—C18—C13	0.8 (2)
C3—C4—C5—C6	1.4 (2)	C18—C13—C14—C15	−1.2 (2)
C4—C5—C6—C7	−0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.938 (19)	2.021 (19)	2.8778 (14)	151.1 (15)

Symmetry code: (i) x, −y+3/2, z−1/2.

2-[4-(4-Fluorophenoxy)pyridin-2-yl]-1H-1,3-benzodiazole (B3)

Crystal data

C18H12FN3O	Dx = 1.393 Mg m^−3
Mr = 305.31	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 24629 reflections
a = 9.91438 (15) Å	θ = 4.7–78.6°
b = 9.90501 (15) Å	µ = 0.81 mm^−1
c = 29.6408 (4) Å	T = 100 K
V = 2910.78 (7) Å^3	Block, clear light brown
Z = 8	0.73 × 0.10 × 0.08 mm
F(000) = 1264

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector	2991 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2777 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.089
Detector resolution: 5.8140 pixels mm^-1	θmax = 78.7°, θmin = 3.0°
ω scans	h = −11→12
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2023)	k = −11→12
Tmin = 0.424, Tmax = 1.000	l = −35→36
45410 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.9564P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.101	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.28 e Å^−3
2991 reflections	Δρmin = −0.23 e Å^−3
212 parameters	Extinction correction: SHELXL-2019/2 (Sheldrick 2019), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00077 (14)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.71449 (9)	−0.03890 (9)	0.51292 (3)	0.0485 (3)
O1	0.38866 (9)	0.37489 (9)	0.56804 (3)	0.0323 (2)
N1	0.77708 (10)	0.72855 (10)	0.67477 (3)	0.0214 (2)
H1	0.7379 (14)	0.8126 (15)	0.6716 (5)	0.026*
N2	0.80628 (10)	0.50410 (9)	0.67013 (3)	0.0214 (2)
N3	0.51128 (10)	0.70449 (11)	0.64462 (4)	0.0290 (2)
C1	0.72521 (11)	0.60747 (11)	0.66194 (4)	0.0209 (2)
C2	0.90391 (12)	0.70266 (11)	0.69204 (3)	0.0211 (3)
C3	1.00568 (12)	0.78775 (12)	0.70779 (4)	0.0250 (3)
H3	0.993116	0.882643	0.709822	0.030*
C4	1.12558 (13)	0.72742 (13)	0.72030 (4)	0.0275 (3)
H4	1.197241	0.782161	0.731161	0.033*
C5	1.14423 (13)	0.58678 (13)	0.71735 (4)	0.0274 (3)
H5	1.228155	0.548968	0.726263	0.033*
C6	1.04348 (12)	0.50243 (12)	0.70180 (4)	0.0240 (3)
H6	1.056669	0.407609	0.699859	0.029*
C7	0.92108 (12)	0.56193 (11)	0.68899 (3)	0.0210 (2)
C8	0.59324 (11)	0.59771 (12)	0.63931 (4)	0.0226 (3)
C9	0.56187 (12)	0.48401 (11)	0.61366 (4)	0.0223 (2)
H9	0.624387	0.412068	0.610192	0.027*
C10	0.43571 (12)	0.48002 (12)	0.59339 (4)	0.0248 (3)
C11	0.34880 (13)	0.58854 (14)	0.59851 (4)	0.0310 (3)
H11	0.262244	0.588250	0.584767	0.037*
C12	0.39107 (14)	0.69701 (14)	0.62406 (5)	0.0337 (3)
H12	0.331115	0.771192	0.627297	0.040*
C13	0.47788 (12)	0.27181 (13)	0.55537 (4)	0.0267 (3)
C14	0.49642 (12)	0.16264 (14)	0.58345 (4)	0.0302 (3)
H14	0.454715	0.160204	0.612294	0.036*
C15	0.57679 (14)	0.05614 (14)	0.56911 (4)	0.0331 (3)
H15	0.590435	−0.020810	0.587690	0.040*
C16	0.63625 (13)	0.06515 (14)	0.52717 (5)	0.0333 (3)
C17	0.61887 (14)	0.17365 (14)	0.49899 (5)	0.0347 (3)
H17	0.661681	0.176497	0.470330	0.042*
C18	0.53741 (13)	0.27903 (13)	0.51329 (4)	0.0308 (3)
H18	0.522707	0.355154	0.494428	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0456 (5)	0.0384 (5)	0.0613 (6)	0.0139 (4)	−0.0028 (4)	−0.0159 (4)
O1	0.0241 (4)	0.0356 (5)	0.0374 (5)	0.0036 (4)	−0.0069 (4)	−0.0128 (4)
N1	0.0255 (5)	0.0170 (5)	0.0217 (5)	0.0012 (4)	0.0003 (4)	−0.0006 (4)
N2	0.0249 (5)	0.0185 (5)	0.0208 (5)	−0.0004 (4)	−0.0003 (4)	0.0007 (3)
N3	0.0285 (5)	0.0257 (6)	0.0328 (5)	0.0052 (4)	−0.0022 (4)	−0.0032 (4)
C1	0.0249 (6)	0.0184 (6)	0.0192 (5)	−0.0004 (4)	0.0023 (4)	−0.0001 (4)
C2	0.0271 (6)	0.0198 (6)	0.0166 (5)	0.0002 (4)	0.0016 (4)	0.0006 (4)
C3	0.0347 (6)	0.0201 (6)	0.0202 (5)	−0.0028 (5)	−0.0007 (5)	−0.0010 (4)
C4	0.0325 (6)	0.0264 (6)	0.0236 (6)	−0.0056 (5)	−0.0053 (5)	−0.0003 (5)
C5	0.0296 (6)	0.0271 (6)	0.0255 (6)	0.0002 (5)	−0.0056 (5)	0.0033 (5)
C6	0.0305 (6)	0.0201 (6)	0.0214 (5)	0.0008 (5)	−0.0018 (4)	0.0024 (4)
C7	0.0278 (6)	0.0181 (5)	0.0172 (5)	−0.0013 (4)	0.0003 (4)	0.0007 (4)
C8	0.0249 (6)	0.0217 (6)	0.0211 (5)	0.0005 (4)	0.0021 (4)	0.0019 (4)
C9	0.0233 (5)	0.0213 (6)	0.0223 (5)	0.0015 (4)	0.0010 (4)	0.0007 (4)
C10	0.0256 (6)	0.0276 (6)	0.0210 (5)	−0.0005 (5)	−0.0001 (4)	−0.0016 (4)
C11	0.0253 (6)	0.0364 (7)	0.0313 (6)	0.0057 (5)	−0.0036 (5)	−0.0029 (5)
C12	0.0306 (6)	0.0324 (7)	0.0383 (7)	0.0107 (5)	−0.0030 (5)	−0.0050 (6)
C13	0.0216 (6)	0.0281 (6)	0.0303 (6)	−0.0014 (5)	−0.0049 (5)	−0.0081 (5)
C14	0.0284 (6)	0.0375 (7)	0.0248 (6)	−0.0045 (5)	−0.0061 (5)	−0.0035 (5)
C15	0.0358 (7)	0.0297 (7)	0.0339 (7)	−0.0015 (6)	−0.0131 (5)	−0.0013 (5)
C16	0.0288 (6)	0.0301 (7)	0.0411 (7)	0.0026 (5)	−0.0044 (5)	−0.0116 (5)
C17	0.0333 (7)	0.0350 (7)	0.0357 (7)	−0.0042 (6)	0.0077 (5)	−0.0058 (6)
C18	0.0313 (6)	0.0270 (7)	0.0342 (7)	−0.0039 (5)	0.0021 (5)	0.0003 (5)

Geometric parameters (Å, º)

F1—C16	1.3573 (15)	C6—H6	0.9500
O1—C10	1.3662 (14)	C6—C7	1.4014 (17)
O1—C13	1.4021 (15)	C8—C9	1.3938 (16)
N1—H1	0.923 (15)	C9—H9	0.9500
N1—C1	1.3593 (15)	C9—C10	1.3882 (17)
N1—C2	1.3816 (15)	C10—C11	1.3860 (18)
N2—C1	1.3241 (15)	C11—H11	0.9500
N2—C7	1.3915 (15)	C11—C12	1.3796 (19)
N3—C8	1.3430 (15)	C12—H12	0.9500
N3—C12	1.3406 (17)	C13—C14	1.3767 (18)
C1—C8	1.4735 (16)	C13—C18	1.3817 (18)
C2—C3	1.3952 (16)	C14—H14	0.9500
C2—C7	1.4072 (16)	C14—C15	1.3887 (19)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.3812 (18)	C15—C16	1.379 (2)
C4—H4	0.9500	C16—C17	1.372 (2)
C4—C5	1.4080 (18)	C17—H17	0.9500
C5—H5	0.9500	C17—C18	1.3862 (19)
C5—C6	1.3813 (17)	C18—H18	0.9500
C10—O1—C13	119.14 (9)	C8—C9—H9	121.3
C1—N1—H1	127.5 (9)	C10—C9—C8	117.39 (11)
C1—N1—C2	106.51 (9)	C10—C9—H9	121.3
C2—N1—H1	126.0 (9)	O1—C10—C9	124.57 (11)
C1—N2—C7	104.59 (9)	O1—C10—C11	116.05 (11)
C12—N3—C8	116.17 (11)	C11—C10—C9	119.38 (11)
N1—C1—C8	121.42 (10)	C10—C11—H11	120.8
N2—C1—N1	113.66 (10)	C12—C11—C10	118.38 (11)
N2—C1—C8	124.87 (10)	C12—C11—H11	120.8
N1—C2—C3	132.07 (11)	N3—C12—C11	124.24 (12)
N1—C2—C7	105.68 (10)	N3—C12—H12	117.9
C3—C2—C7	122.17 (11)	C11—C12—H12	117.9
C2—C3—H3	121.6	C14—C13—O1	119.63 (11)
C4—C3—C2	116.80 (11)	C14—C13—C18	121.96 (12)
C4—C3—H3	121.6	C18—C13—O1	118.26 (12)
C3—C4—H4	119.2	C13—C14—H14	120.4
C3—C4—C5	121.63 (11)	C13—C14—C15	119.22 (12)
C5—C4—H4	119.2	C15—C14—H14	120.4
C4—C5—H5	119.2	C14—C15—H15	120.9
C6—C5—C4	121.61 (12)	C16—C15—C14	118.17 (12)
C6—C5—H5	119.2	C16—C15—H15	120.9
C5—C6—H6	121.2	F1—C16—C15	118.41 (13)
C5—C6—C7	117.53 (11)	F1—C16—C17	118.50 (12)
C7—C6—H6	121.2	C17—C16—C15	123.09 (12)
N2—C7—C2	109.55 (10)	C16—C17—H17	120.8
N2—C7—C6	130.09 (11)	C16—C17—C18	118.48 (12)
C6—C7—C2	120.26 (11)	C18—C17—H17	120.8
N3—C8—C1	115.60 (10)	C13—C18—C17	119.08 (12)
N3—C8—C9	124.42 (11)	C13—C18—H18	120.5
C9—C8—C1	119.96 (10)	C17—C18—H18	120.5
F1—C16—C17—C18	179.10 (12)	C5—C6—C7—N2	176.14 (11)
O1—C10—C11—C12	179.58 (11)	C5—C6—C7—C2	0.17 (16)
O1—C13—C14—C15	175.05 (11)	C7—N2—C1—N1	−1.16 (12)
O1—C13—C18—C17	−175.77 (11)	C7—N2—C1—C8	176.20 (10)
N1—C1—C8—N3	−19.81 (15)	C7—C2—C3—C4	0.20 (16)
N1—C1—C8—C9	158.86 (11)	C8—N3—C12—C11	0.0 (2)
N1—C2—C3—C4	−175.97 (11)	C8—C9—C10—O1	−178.59 (11)
N1—C2—C7—N2	0.06 (12)	C8—C9—C10—C11	1.44 (17)
N1—C2—C7—C6	176.79 (9)	C9—C10—C11—C12	−0.44 (18)
N2—C1—C8—N3	163.02 (11)	C10—O1—C13—C14	88.48 (14)
N2—C1—C8—C9	−18.30 (16)	C10—O1—C13—C18	−96.03 (13)
N3—C8—C9—C10	−1.89 (17)	C10—C11—C12—N3	−0.3 (2)
C1—N1—C2—C3	175.90 (11)	C12—N3—C8—C1	179.78 (11)
C1—N1—C2—C7	−0.73 (11)	C12—N3—C8—C9	1.18 (18)
C1—N2—C7—C2	0.64 (12)	C13—O1—C10—C9	−10.10 (17)
C1—N2—C7—C6	−175.67 (11)	C13—O1—C10—C11	169.87 (11)
C1—C8—C9—C10	179.56 (10)	C13—C14—C15—C16	0.69 (18)
C2—N1—C1—N2	1.23 (12)	C14—C13—C18—C17	−0.39 (19)
C2—N1—C1—C8	−176.24 (9)	C14—C15—C16—F1	−179.75 (11)
C2—C3—C4—C5	−0.07 (17)	C14—C15—C16—C17	−0.5 (2)
C3—C2—C7—N2	−176.98 (9)	C15—C16—C17—C18	−0.2 (2)
C3—C2—C7—C6	−0.25 (16)	C16—C17—C18—C13	0.61 (19)
C3—C4—C5—C6	0.00 (18)	C18—C13—C14—C15	−0.28 (18)
C4—C5—C6—C7	−0.05 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.923 (15)	1.947 (15)	2.8550 (14)	167.3 (13)
C6—H6···N3^ii	0.95	2.68	3.4461 (16)	138
C15—H15···N2^ii	0.95	2.66	3.2520 (15)	121
C17—H17···O1^iii	0.95	2.57	3.3664 (16)	141

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) x+1/2, −y+1/2, −z+1.