A 1:1 flavone cocrystal with cyclic trimeric perfluoro-o-phenyl­enemercury

In the title compound, mol­ecules are connected by Hg...O inter­actions. The 1:1 complexes pack in zigzag chains where they stack via two alternating stacking patterns, TPPM(cyclic trimeric perfluoro-o-phenyl­enemercury)–TPPM, and FLA(flavone)–FLA. The shortened F...F, CH...F and CH...π contacts consolidate the crystal structure.

Computing details

Tris(µ₂-perfluoro-o-phenylene)(µ₂-3-phenyl-4H-chromen-4-one)-triangulo-trimercury

Crystal data

[Hg3(C6F4)3(C15H10O2)]	F(000) = 2288
Mr = 1268.18	Dx = 2.788 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4181 (8) Å	Cell parameters from 9132 reflections
b = 13.8092 (8) Å	θ = 2.2–26.7°
c = 17.6498 (11) Å	µ = 15.31 mm^−1
β = 93.360 (2)°	T = 100 K
V = 3021.5 (3) Å^3	Plate, clear colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer	5894 independent reflections
Radiation source: sealed X-ray tube, EIGENMANN GmbH	5069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 7.9 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→17
Tmin = 0.372, Tmax = 0.746	l = −21→16
38196 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.052	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0252P)^2 + 1.6597P] where P = (Fo^2 + 2Fc^2)/3
5894 reflections	(Δ/σ)max = 0.003
451 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −1.19 e Å^−3

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
Hg1	0.85812 (2)	0.44283 (2)	0.60352 (2)	0.03572 (6)
Hg2	0.86702 (2)	0.46865 (2)	0.40075 (2)	0.03547 (6)
Hg3	0.84037 (2)	0.68004 (2)	0.51822 (2)	0.03658 (6)
F1	0.8927 (3)	0.2205 (2)	0.63984 (17)	0.0536 (8)
F2	0.9080 (3)	0.0628 (2)	0.5516 (2)	0.0729 (11)
F3	0.9084 (3)	0.0823 (2)	0.3984 (2)	0.0777 (12)
F4	0.8941 (3)	0.2590 (2)	0.33427 (17)	0.0561 (9)
F5	0.8718 (3)	0.5418 (2)	0.23224 (18)	0.0688 (10)
F6	0.8452 (3)	0.7185 (3)	0.16752 (18)	0.0751 (11)
F7	0.8183 (3)	0.8760 (2)	0.2553 (2)	0.0702 (10)
F8	0.8354 (3)	0.8603 (2)	0.4079 (2)	0.0646 (10)
F9	0.8232 (3)	0.8296 (2)	0.65175 (18)	0.0565 (9)
F10	0.8092 (3)	0.8092 (2)	0.80319 (17)	0.0571 (9)
F11	0.8165 (3)	0.6306 (2)	0.86695 (16)	0.0552 (8)
F12	0.8461 (3)	0.4725 (2)	0.78054 (18)	0.0583 (9)
O1	0.6883 (3)	0.5027 (2)	0.50025 (18)	0.0383 (8)
O2	0.4563 (3)	0.3256 (2)	0.40217 (19)	0.0379 (8)
C1	0.8790 (4)	0.3342 (3)	0.4535 (3)	0.0365 (12)
C2	0.8910 (4)	0.2518 (4)	0.4107 (3)	0.0404 (12)
C3	0.8998 (5)	0.1606 (4)	0.4419 (3)	0.0470 (14)
C4	0.8998 (5)	0.1504 (4)	0.5191 (3)	0.0491 (14)
C5	0.8890 (4)	0.2323 (4)	0.5636 (3)	0.0395 (12)
C6	0.8776 (4)	0.3242 (3)	0.5331 (3)	0.0345 (11)
C7	0.8593 (4)	0.6074 (3)	0.3557 (3)	0.0352 (11)
C8	0.8596 (4)	0.6197 (4)	0.2781 (3)	0.0438 (13)
C9	0.8465 (4)	0.7088 (4)	0.2435 (3)	0.0469 (14)
C10	0.8346 (4)	0.7894 (4)	0.2882 (3)	0.0451 (14)
C11	0.8394 (4)	0.7791 (4)	0.3655 (3)	0.0443 (13)
C12	0.8482 (4)	0.6903 (4)	0.4009 (3)	0.0348 (11)
C13	0.8368 (4)	0.6593 (4)	0.6347 (3)	0.0359 (11)
C14	0.8278 (4)	0.7389 (4)	0.6815 (3)	0.0398 (12)
C15	0.8211 (4)	0.7302 (4)	0.7593 (3)	0.0411 (13)
C16	0.8264 (4)	0.6408 (4)	0.7915 (3)	0.0422 (13)
C17	0.8405 (4)	0.5607 (4)	0.7459 (3)	0.0406 (12)
C18	0.8448 (4)	0.5670 (4)	0.6683 (3)	0.0391 (12)
C19	0.6156 (4)	0.4494 (3)	0.4705 (3)	0.0304 (10)
C20	0.5632 (4)	0.4696 (3)	0.3954 (3)	0.0307 (10)
C21	0.5875 (4)	0.5526 (3)	0.3525 (3)	0.0361 (12)
H21	0.6385	0.5985	0.3727	0.043*
C22	0.5381 (4)	0.5673 (4)	0.2823 (3)	0.0463 (14)
H22	0.5544	0.6234	0.2541	0.056*
C23	0.4647 (5)	0.5010 (4)	0.2524 (3)	0.0479 (14)
H23	0.4318	0.5114	0.2031	0.058*
C24	0.4380 (4)	0.4199 (4)	0.2926 (3)	0.0431 (13)
H24	0.3870	0.3744	0.2719	0.052*
C25	0.4880 (4)	0.4066 (3)	0.3643 (3)	0.0328 (11)
C26	0.5780 (4)	0.3633 (3)	0.5056 (3)	0.0335 (11)
H26	0.6081	0.3460	0.5545	0.040*
C27	0.5022 (4)	0.3063 (3)	0.4723 (3)	0.0346 (11)
C28	0.4558 (4)	0.2176 (3)	0.5049 (3)	0.0378 (12)
C29	0.4084 (5)	0.1470 (4)	0.4570 (3)	0.0544 (15)
H29	0.4040	0.1560	0.4036	0.065*
C30	0.3682 (6)	0.0639 (4)	0.4884 (4)	0.0685 (19)
H30	0.3353	0.0161	0.4560	0.082*
C31	0.3747 (5)	0.0488 (4)	0.5655 (4)	0.0621 (17)
H31	0.3485	−0.0096	0.5861	0.075*
C32	0.4189 (5)	0.1186 (4)	0.6118 (3)	0.0548 (15)
H32	0.4214	0.1097	0.6653	0.066*
C33	0.4605 (4)	0.2024 (4)	0.5820 (3)	0.0451 (13)
H33	0.4926	0.2499	0.6151	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.03653 (11)	0.03970 (11)	0.03063 (12)	−0.00036 (8)	−0.00069 (9)	−0.00388 (8)
Hg2	0.03836 (12)	0.03602 (11)	0.03231 (12)	0.00085 (8)	0.00439 (9)	−0.00019 (8)
Hg3	0.03959 (12)	0.04065 (11)	0.02955 (12)	−0.00449 (8)	0.00228 (9)	−0.00388 (8)
F1	0.064 (2)	0.0567 (19)	0.0405 (19)	0.0088 (16)	0.0019 (16)	0.0120 (15)
F2	0.102 (3)	0.0436 (19)	0.074 (3)	0.0153 (18)	0.010 (2)	0.0131 (17)
F3	0.122 (3)	0.0389 (18)	0.074 (3)	0.012 (2)	0.017 (2)	−0.0130 (17)
F4	0.077 (2)	0.0521 (19)	0.0403 (19)	0.0064 (17)	0.0113 (17)	−0.0080 (14)
F5	0.106 (3)	0.064 (2)	0.038 (2)	0.003 (2)	0.015 (2)	−0.0125 (16)
F6	0.096 (3)	0.094 (3)	0.036 (2)	0.001 (2)	0.0106 (19)	0.0207 (18)
F7	0.079 (3)	0.054 (2)	0.079 (3)	0.0043 (18)	0.017 (2)	0.0299 (18)
F8	0.080 (2)	0.0400 (18)	0.075 (2)	−0.0009 (17)	0.015 (2)	−0.0028 (16)
F9	0.081 (2)	0.0413 (18)	0.047 (2)	−0.0048 (16)	−0.0001 (18)	−0.0047 (14)
F10	0.072 (2)	0.057 (2)	0.0425 (19)	−0.0012 (16)	0.0048 (17)	−0.0203 (15)
F11	0.061 (2)	0.076 (2)	0.0272 (17)	0.0027 (17)	−0.0009 (15)	−0.0049 (15)
F12	0.080 (2)	0.0523 (19)	0.0422 (19)	0.0006 (17)	−0.0017 (18)	0.0052 (15)
O1	0.0331 (19)	0.043 (2)	0.038 (2)	−0.0075 (16)	−0.0073 (16)	−0.0013 (16)
O2	0.041 (2)	0.0398 (19)	0.032 (2)	−0.0084 (15)	−0.0041 (16)	0.0024 (14)
C1	0.031 (3)	0.034 (3)	0.045 (3)	0.003 (2)	0.002 (2)	0.001 (2)
C2	0.046 (3)	0.044 (3)	0.032 (3)	0.004 (2)	0.005 (2)	−0.004 (2)
C3	0.061 (4)	0.033 (3)	0.047 (4)	0.003 (3)	0.006 (3)	−0.010 (2)
C4	0.052 (3)	0.033 (3)	0.062 (4)	0.008 (3)	0.001 (3)	0.005 (3)
C5	0.035 (3)	0.051 (3)	0.032 (3)	0.000 (2)	−0.003 (2)	0.003 (2)
C6	0.031 (3)	0.038 (3)	0.035 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
C7	0.032 (3)	0.042 (3)	0.032 (3)	−0.002 (2)	0.004 (2)	0.001 (2)
C8	0.050 (3)	0.047 (3)	0.035 (3)	−0.003 (2)	0.014 (3)	−0.003 (2)
C9	0.042 (3)	0.067 (4)	0.033 (3)	−0.001 (3)	0.003 (3)	0.011 (3)
C10	0.040 (3)	0.042 (3)	0.053 (4)	−0.001 (2)	0.007 (3)	0.021 (3)
C11	0.043 (3)	0.035 (3)	0.056 (4)	−0.006 (2)	0.011 (3)	−0.002 (3)
C12	0.025 (2)	0.046 (3)	0.034 (3)	−0.003 (2)	0.001 (2)	0.003 (2)
C13	0.032 (3)	0.047 (3)	0.029 (3)	−0.006 (2)	0.002 (2)	−0.006 (2)
C14	0.038 (3)	0.044 (3)	0.037 (3)	−0.007 (2)	0.001 (2)	−0.003 (2)
C15	0.038 (3)	0.047 (3)	0.038 (3)	−0.003 (2)	0.001 (2)	−0.017 (2)
C16	0.040 (3)	0.060 (3)	0.026 (3)	−0.004 (3)	−0.002 (2)	−0.010 (2)
C17	0.038 (3)	0.045 (3)	0.038 (3)	−0.002 (2)	−0.005 (2)	0.000 (2)
C18	0.036 (3)	0.052 (3)	0.029 (3)	−0.004 (2)	−0.001 (2)	−0.008 (2)
C19	0.026 (2)	0.039 (3)	0.026 (3)	0.004 (2)	−0.001 (2)	−0.003 (2)
C20	0.023 (2)	0.040 (3)	0.029 (3)	0.001 (2)	0.000 (2)	0.000 (2)
C21	0.031 (3)	0.037 (3)	0.040 (3)	0.000 (2)	0.005 (2)	0.003 (2)
C22	0.051 (3)	0.046 (3)	0.042 (3)	0.006 (3)	0.006 (3)	0.013 (2)
C23	0.052 (4)	0.058 (4)	0.032 (3)	0.001 (3)	−0.007 (3)	0.006 (3)
C24	0.040 (3)	0.054 (3)	0.034 (3)	−0.006 (2)	−0.008 (2)	0.000 (2)
C25	0.024 (2)	0.042 (3)	0.033 (3)	0.000 (2)	0.004 (2)	0.003 (2)
C26	0.035 (3)	0.042 (3)	0.024 (3)	−0.001 (2)	−0.001 (2)	0.003 (2)
C27	0.036 (3)	0.043 (3)	0.024 (3)	0.002 (2)	−0.004 (2)	0.003 (2)
C28	0.036 (3)	0.035 (3)	0.043 (3)	−0.001 (2)	0.001 (2)	0.002 (2)
C29	0.065 (4)	0.050 (3)	0.049 (4)	−0.016 (3)	0.001 (3)	0.001 (3)
C30	0.084 (5)	0.053 (4)	0.069 (5)	−0.024 (3)	0.005 (4)	−0.008 (3)
C31	0.068 (4)	0.049 (4)	0.071 (5)	−0.013 (3)	0.007 (4)	0.015 (3)
C32	0.060 (4)	0.055 (4)	0.049 (4)	−0.004 (3)	0.007 (3)	0.018 (3)
C33	0.042 (3)	0.045 (3)	0.048 (4)	−0.001 (2)	−0.003 (3)	0.006 (2)

Geometric parameters (Å, º)

Hg1—C18	2.072 (5)	C13—C14	1.383 (7)
Hg1—C6	2.079 (5)	C13—C18	1.407 (7)
Hg2—C7	2.074 (5)	C14—C15	1.387 (7)
Hg2—C1	2.079 (5)	C15—C16	1.358 (7)
Hg3—C13	2.079 (5)	C16—C17	1.385 (7)
Hg3—C12	2.084 (5)	C17—C18	1.377 (7)
F1—C5	1.355 (6)	C19—C26	1.432 (6)
F2—C4	1.338 (6)	C19—C20	1.468 (6)
F3—C3	1.335 (6)	C20—C25	1.368 (6)
F4—C2	1.356 (6)	C20—C21	1.416 (6)
F5—C8	1.359 (6)	C21—C22	1.364 (7)
F6—C9	1.347 (6)	C21—H21	0.9500
F7—C10	1.339 (6)	C22—C23	1.374 (8)
F8—C11	1.351 (6)	C22—H22	0.9500
F9—C14	1.358 (6)	C23—C24	1.377 (7)
F10—C15	1.352 (5)	C23—H23	0.9500
F11—C16	1.352 (6)	C24—C25	1.388 (7)
F12—C17	1.363 (6)	C24—H24	0.9500
O1—C19	1.256 (5)	C26—C27	1.337 (7)
O2—C27	1.358 (6)	C26—H26	0.9500
O2—C25	1.373 (5)	C27—C28	1.484 (6)
C1—C2	1.378 (6)	C28—C33	1.374 (7)
C1—C6	1.413 (7)	C28—C29	1.397 (7)
C2—C3	1.376 (7)	C29—C30	1.380 (8)
C3—C4	1.371 (8)	C29—H29	0.9500
C4—C5	1.388 (7)	C30—C31	1.374 (9)
C5—C6	1.382 (7)	C30—H30	0.9500
C7—C8	1.381 (7)	C31—C32	1.358 (8)
C7—C12	1.406 (7)	C31—H31	0.9500
C8—C9	1.379 (7)	C32—C33	1.385 (7)
C9—C10	1.376 (8)	C32—H32	0.9500
C10—C11	1.370 (8)	C33—H33	0.9500
C11—C12	1.377 (7)
C18—Hg1—C6	175.85 (19)	F12—C17—C18	119.9 (4)
C7—Hg2—C1	175.8 (2)	F12—C17—C16	117.3 (5)
C13—Hg3—C12	175.7 (2)	C18—C17—C16	122.8 (5)
C27—O2—C25	119.1 (4)	C17—C18—C13	118.0 (4)
C2—C1—C6	118.2 (4)	C17—C18—Hg1	120.4 (4)
C2—C1—Hg2	120.0 (4)	C13—C18—Hg1	121.5 (4)
C6—C1—Hg2	121.8 (3)	O1—C19—C26	123.4 (4)
F4—C2—C3	117.3 (4)	O1—C19—C20	122.4 (4)
F4—C2—C1	119.6 (4)	C26—C19—C20	114.2 (4)
C3—C2—C1	123.1 (5)	C25—C20—C21	117.5 (4)
F3—C3—C4	119.6 (5)	C25—C20—C19	119.8 (4)
F3—C3—C2	121.3 (5)	C21—C20—C19	122.7 (4)
C4—C3—C2	119.2 (5)	C22—C21—C20	120.4 (5)
F2—C4—C3	120.9 (5)	C22—C21—H21	119.8
F2—C4—C5	120.2 (5)	C20—C21—H21	119.8
C3—C4—C5	118.9 (5)	C21—C22—C23	120.2 (5)
F1—C5—C6	119.7 (4)	C21—C22—H22	119.9
F1—C5—C4	117.6 (5)	C23—C22—H22	119.9
C6—C5—C4	122.7 (5)	C22—C23—C24	121.2 (5)
C5—C6—C1	118.0 (4)	C22—C23—H23	119.4
C5—C6—Hg1	120.2 (4)	C24—C23—H23	119.4
C1—C6—Hg1	121.8 (3)	C23—C24—C25	117.9 (5)
C8—C7—C12	117.9 (4)	C23—C24—H24	121.0
C8—C7—Hg2	119.4 (4)	C25—C24—H24	121.0
C12—C7—Hg2	122.6 (3)	C20—C25—O2	122.1 (4)
F5—C8—C9	117.2 (5)	C20—C25—C24	122.7 (4)
F5—C8—C7	120.0 (5)	O2—C25—C24	115.2 (4)
C9—C8—C7	122.8 (5)	C27—C26—C19	122.5 (5)
F6—C9—C10	119.6 (5)	C27—C26—H26	118.7
F6—C9—C8	121.5 (5)	C19—C26—H26	118.7
C10—C9—C8	118.8 (5)	C26—C27—O2	122.2 (4)
F7—C10—C11	121.4 (5)	C26—C27—C28	126.5 (5)
F7—C10—C9	119.5 (5)	O2—C27—C28	111.3 (4)
C11—C10—C9	119.1 (5)	C33—C28—C29	118.9 (5)
F8—C11—C10	117.7 (5)	C33—C28—C27	120.9 (5)
F8—C11—C12	119.5 (5)	C29—C28—C27	120.1 (5)
C10—C11—C12	122.8 (5)	C30—C29—C28	119.2 (6)
C11—C12—C7	118.4 (5)	C30—C29—H29	120.4
C11—C12—Hg3	120.2 (4)	C28—C29—H29	120.4
C7—C12—Hg3	121.3 (3)	C31—C30—C29	121.5 (6)
C14—C13—C18	118.3 (4)	C31—C30—H30	119.3
C14—C13—Hg3	119.2 (4)	C29—C30—H30	119.3
C18—C13—Hg3	122.5 (3)	C32—C31—C30	119.1 (5)
F9—C14—C13	120.4 (4)	C32—C31—H31	120.4
F9—C14—C15	117.3 (4)	C30—C31—H31	120.4
C13—C14—C15	122.3 (5)	C31—C32—C33	120.7 (6)
F10—C15—C16	119.9 (5)	C31—C32—H32	119.6
F10—C15—C14	120.8 (5)	C33—C32—H32	119.6
C16—C15—C14	119.2 (4)	C28—C33—C32	120.6 (5)
F11—C16—C15	120.1 (4)	C28—C33—H33	119.7
F11—C16—C17	120.7 (5)	C32—C33—H33	119.7
C15—C16—C17	119.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···F4^i	0.95	2.54	3.486 (6)	173
C24—H24···F1^ii	0.95	2.68	3.342 (6)	127
C30—H30···F11^ii	0.95	2.57	3.473 (7)	160
C31—H31···F5^iii	0.95	2.62	3.200 (8)	120
C32—H32···F5^iii	0.95	2.50	3.149 (6)	126
C21—H21···C7	0.95	2.78	3.456 (7)	129
C24—H24···C16^iv	0.95	2.82	3.621 (7)	142

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