Synthesis, structure and in vitro cyto­toxicity testing of some 2-aroylbenzo­furan-3-ols

Five 2-aroyl-5-bromo­benzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodo­benzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and ¹H NMR and ¹³C NMR spectroscopy. Single-crystal X-ray diffraction studies of four com­pounds, namely, (5-bromo-3-hy­droxy­benzo­furan-2-yl)(4-fluoro­phen­yl)me­tha­none, C₁₅H₈BrFO₃, (5-bromo-3-hy­droxy­benzo­furan-2-yl)(4-chloro­phen­yl)metha­none, C₁₅H₈BrClO₃, (5-bromo-3-hy­droxy­benzo­furan-2-yl)(4-bromo­phen­yl)methanone, C₁₅H₈Br₂O₃, and (4-bromo­phen­yl)(3-hy­droxy-5-iodo­benzo­furan-2-yl)methanone, C₁₅H₈BrIO₃, were also carried out. The compounds were tested for their in vitro cyto­toxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC₅₀ values of 1.39–8.03 µM.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for (4a); SHELXS (Sheldrick, 2008) for (4b); SHELXT (Sheldrick, 2015a) for (4c), (4h). For all structures, program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(5-Bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone (4a)

Crystal data

C15H8BrFO3	F(000) = 664
Mr = 335.12	Dx = 1.780 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8598 (4) Å	Cell parameters from 2736 reflections
b = 11.7229 (10) Å	θ = 2.9–25.3°
c = 27.679 (2) Å	µ = 3.30 mm^−1
β = 93.255 (9)°	T = 293 K
V = 1250.38 (19) Å^3	Needle, yellow
Z = 4	0.5 × 0.15 × 0.05 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Eos detector	2543 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1873 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.8°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −14→14
Tmin = 0.447, Tmax = 1.000	l = −34→33
7646 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.4417P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2543 reflections	Δρmax = 0.44 e Å^−3
185 parameters	Δρmin = −0.45 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
O1	1.0511 (7)	0.33866 (19)	0.35954 (8)	0.0346 (6)
C2	0.9792 (10)	0.4552 (3)	0.36548 (12)	0.0331 (9)
C3	0.8510 (10)	0.4728 (3)	0.40944 (12)	0.0356 (9)
C4	0.8335 (9)	0.3665 (3)	0.43395 (12)	0.0307 (8)
C5	0.7327 (10)	0.3302 (3)	0.47925 (13)	0.0356 (9)
H5	0.648929	0.381124	0.501555	0.043*
C6	0.7633 (10)	0.2170 (3)	0.48907 (12)	0.0363 (9)
C7	0.8901 (10)	0.1380 (3)	0.45616 (13)	0.0394 (10)
H7	0.905416	0.061294	0.464530	0.047*
C8	0.9913 (11)	0.1730 (3)	0.41188 (13)	0.0383 (9)
H8	1.076432	0.121809	0.389793	0.046*
C9	0.9610 (9)	0.2874 (3)	0.40168 (12)	0.0319 (8)
C10	1.0400 (10)	0.5412 (3)	0.33035 (12)	0.0350 (9)
O11	0.9820 (8)	0.6415 (2)	0.34270 (9)	0.0525 (8)
C12	1.1635 (9)	0.5177 (3)	0.28145 (12)	0.0318 (8)
C13	1.2995 (10)	0.6084 (3)	0.25606 (13)	0.0375 (9)
H13	1.319832	0.679808	0.270563	0.045*
C14	1.4041 (10)	0.5935 (4)	0.20979 (13)	0.0433 (10)
H14	1.497366	0.653718	0.192927	0.052*
C15	1.3676 (11)	0.4884 (4)	0.18939 (13)	0.0420 (10)
C16	1.2279 (10)	0.3965 (3)	0.21210 (13)	0.0401 (10)
H16	1.200229	0.326544	0.196515	0.048*
C17	1.1296 (10)	0.4116 (3)	0.25904 (12)	0.0372 (9)
H17	1.040261	0.350361	0.275726	0.045*
F18	1.4709 (7)	0.4732 (2)	0.14395 (7)	0.0633 (8)
O19	0.7528 (9)	0.5730 (2)	0.42805 (11)	0.0509 (8)
Br20	0.63812 (11)	0.16145 (4)	0.55017 (2)	0.04886 (17)
H19	0.805 (12)	0.618 (4)	0.4097 (15)	0.053 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0478 (16)	0.0302 (12)	0.0266 (13)	0.0059 (13)	0.0097 (11)	0.0023 (10)
C2	0.041 (2)	0.0301 (19)	0.0289 (19)	0.0024 (18)	0.0076 (17)	−0.0044 (15)
C3	0.041 (2)	0.032 (2)	0.035 (2)	0.0031 (19)	0.0037 (18)	−0.0042 (16)
C4	0.031 (2)	0.0329 (19)	0.0286 (18)	0.0021 (17)	0.0047 (16)	−0.0016 (15)
C5	0.037 (2)	0.038 (2)	0.0318 (19)	0.003 (2)	0.0079 (17)	−0.0037 (17)
C6	0.033 (2)	0.042 (2)	0.034 (2)	−0.002 (2)	0.0049 (17)	0.0035 (17)
C7	0.047 (3)	0.032 (2)	0.039 (2)	0.0041 (19)	0.0029 (19)	0.0052 (16)
C8	0.052 (3)	0.033 (2)	0.030 (2)	0.006 (2)	0.0091 (18)	−0.0004 (16)
C9	0.034 (2)	0.036 (2)	0.0262 (18)	0.0014 (18)	0.0038 (16)	−0.0002 (16)
C10	0.044 (2)	0.032 (2)	0.0295 (19)	−0.0017 (19)	0.0060 (17)	−0.0022 (16)
O11	0.088 (2)	0.0311 (15)	0.0398 (16)	0.0041 (15)	0.0131 (15)	−0.0022 (12)
C12	0.031 (2)	0.0325 (19)	0.0317 (19)	0.0009 (17)	0.0004 (16)	0.0037 (15)
C13	0.044 (2)	0.032 (2)	0.037 (2)	0.0002 (19)	0.0028 (18)	0.0031 (16)
C14	0.045 (3)	0.049 (3)	0.037 (2)	−0.002 (2)	0.009 (2)	0.0125 (19)
C15	0.041 (2)	0.056 (3)	0.029 (2)	0.005 (2)	0.0053 (18)	0.0043 (18)
C16	0.053 (3)	0.034 (2)	0.033 (2)	0.003 (2)	0.0037 (19)	−0.0029 (17)
C17	0.047 (2)	0.035 (2)	0.030 (2)	−0.001 (2)	0.0053 (18)	0.0041 (16)
F18	0.090 (2)	0.0692 (16)	0.0332 (13)	0.0089 (16)	0.0262 (13)	0.0011 (12)
O19	0.080 (2)	0.0301 (15)	0.0444 (17)	0.0080 (16)	0.0208 (16)	−0.0018 (14)
Br20	0.0552 (3)	0.0534 (3)	0.0396 (3)	0.0052 (2)	0.0172 (2)	0.01369 (19)

Geometric parameters (Å, º)

O1—C2	1.406 (4)	C8—C9	1.374 (5)
O1—C9	1.374 (4)	C10—O11	1.249 (4)
C2—C3	1.355 (5)	C10—C12	1.486 (5)
C2—C10	1.429 (5)	C12—C13	1.393 (5)
C3—C4	1.422 (5)	C12—C17	1.393 (5)
C3—O19	1.345 (4)	C13—H13	0.9300
C4—C5	1.400 (5)	C13—C14	1.376 (5)
C4—C9	1.397 (5)	C14—H14	0.9300
C5—H5	0.9300	C14—C15	1.360 (6)
C5—C6	1.358 (5)	C15—C16	1.373 (5)
C6—C7	1.406 (5)	C15—F18	1.353 (4)
C6—Br20	1.900 (3)	C16—H16	0.9300
C7—H7	0.9300	C16—C17	1.385 (5)
C7—C8	1.370 (5)	C17—H17	0.9300
C8—H8	0.9300	O19—H19	0.77 (4)
C9—O1—C2	105.3 (2)	C8—C9—C4	123.1 (3)
O1—C2—C10	124.4 (3)	C2—C10—C12	124.3 (3)
C3—C2—O1	109.7 (3)	O11—C10—C2	116.1 (3)
C3—C2—C10	125.9 (3)	O11—C10—C12	119.7 (3)
C2—C3—C4	108.9 (3)	C13—C12—C10	117.9 (3)
O19—C3—C2	127.0 (3)	C13—C12—C17	119.0 (3)
O19—C3—C4	124.1 (3)	C17—C12—C10	122.9 (3)
C5—C4—C3	135.8 (3)	C12—C13—H13	119.6
C9—C4—C3	104.4 (3)	C14—C13—C12	120.8 (4)
C9—C4—C5	119.8 (3)	C14—C13—H13	119.6
C4—C5—H5	121.6	C13—C14—H14	120.9
C6—C5—C4	116.8 (3)	C15—C14—C13	118.2 (4)
C6—C5—H5	121.6	C15—C14—H14	120.9
C5—C6—C7	122.9 (3)	C14—C15—C16	123.7 (3)
C5—C6—Br20	119.3 (3)	F18—C15—C14	118.5 (3)
C7—C6—Br20	117.8 (3)	F18—C15—C16	117.8 (4)
C6—C7—H7	119.7	C15—C16—H16	121.1
C8—C7—C6	120.7 (3)	C15—C16—C17	117.7 (3)
C8—C7—H7	119.7	C17—C16—H16	121.1
C7—C8—H8	121.6	C12—C17—H17	119.8
C7—C8—C9	116.8 (3)	C16—C17—C12	120.5 (3)
C9—C8—H8	121.6	C16—C17—H17	119.8
O1—C9—C4	111.6 (3)	C3—O19—H19	105 (3)
C8—C9—O1	125.3 (3)
O1—C2—C3—C4	−0.2 (5)	C7—C8—C9—C4	−0.2 (6)
O1—C2—C3—O19	179.9 (4)	C9—O1—C2—C3	0.0 (4)
O1—C2—C10—O11	−175.6 (4)	C9—O1—C2—C10	178.9 (4)
O1—C2—C10—C12	4.6 (6)	C9—C4—C5—C6	−0.6 (6)
C2—O1—C9—C4	0.3 (4)	C10—C2—C3—C4	−179.2 (4)
C2—O1—C9—C8	−179.4 (4)	C10—C2—C3—O19	1.0 (7)
C2—C3—C4—C5	178.8 (4)	C10—C12—C13—C14	−177.1 (4)
C2—C3—C4—C9	0.4 (4)	C10—C12—C17—C16	175.6 (4)
C2—C10—C12—C13	−163.1 (4)	O11—C10—C12—C13	17.1 (6)
C2—C10—C12—C17	20.9 (6)	O11—C10—C12—C17	−158.9 (4)
C3—C2—C10—O11	3.2 (6)	C12—C13—C14—C15	0.7 (6)
C3—C2—C10—C12	−176.6 (4)	C13—C12—C17—C16	−0.4 (6)
C3—C4—C5—C6	−178.8 (4)	C13—C14—C15—C16	0.9 (7)
C3—C4—C9—O1	−0.4 (4)	C13—C14—C15—F18	−179.8 (3)
C3—C4—C9—C8	179.3 (4)	C14—C15—C16—C17	−2.1 (6)
C4—C5—C6—C7	0.2 (6)	C15—C16—C17—C12	1.8 (6)
C4—C5—C6—Br20	179.1 (3)	C17—C12—C13—C14	−1.0 (6)
C5—C4—C9—O1	−179.1 (3)	F18—C15—C16—C17	178.6 (3)
C5—C4—C9—C8	0.6 (6)	O19—C3—C4—C5	−1.4 (8)
C5—C6—C7—C8	0.2 (6)	O19—C3—C4—C9	−179.8 (4)
C6—C7—C8—C9	−0.2 (6)	Br20—C6—C7—C8	−178.7 (3)
C7—C8—C9—O1	179.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O11	0.77 (5)	2.03 (4)	2.692 (4)	144 (4)
C17—H17···O1	0.93	2.32	2.942 (4)	124
C16—H16···O11^i	0.93	2.51	3.428 (4)	170
C5—H5···O19^ii	0.93	2.61	3.454 (5)	150

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

(5-Bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone (4b)

Crystal data

C15H8BrClO3	F(000) = 1392
Mr = 351.57	Dx = 1.747 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.4034 (10) Å	Cell parameters from 6124 reflections
b = 3.9818 (1) Å	θ = 3.1–24.1°
c = 26.2773 (10) Å	µ = 3.28 mm^−1
β = 104.605 (4)°	T = 294 K
V = 2673.34 (17) Å^3	Plate, yellow
Z = 8	0.4 × 0.15 × 0.05 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Eos detector	5419 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3168 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.064
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.4°
ω scans	h = −33→33
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −4→4
Tmin = 0.572, Tmax = 1.000	l = −32→32
27661 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 2.0591P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
5419 reflections	Δρmax = 0.56 e Å^−3
369 parameters	Δρmin = −0.42 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
O1	0.74798 (10)	0.1478 (6)	0.20663 (11)	0.0451 (7)
C2	0.76425 (16)	0.2959 (10)	0.25631 (16)	0.0414 (10)
C3	0.72831 (17)	0.2377 (11)	0.28464 (18)	0.0474 (11)
C4	0.68645 (16)	0.0499 (10)	0.25260 (17)	0.0435 (10)
C5	0.63911 (17)	−0.0788 (11)	0.25851 (19)	0.0520 (12)
H5	0.628733	−0.049134	0.289505	0.062*
C6	0.60870 (16)	−0.2499 (10)	0.2169 (2)	0.0506 (12)
C7	0.62345 (17)	−0.3027 (11)	0.17041 (18)	0.0522 (12)
H7	0.601560	−0.424167	0.143395	0.063*
C8	0.67037 (16)	−0.1771 (10)	0.16363 (18)	0.0488 (11)
H8	0.680793	−0.210610	0.132745	0.059*
C9	0.70068 (16)	0.0011 (9)	0.20560 (17)	0.0422 (11)
C10	0.81144 (17)	0.4852 (10)	0.27453 (19)	0.0504 (12)
O11	0.82009 (13)	0.5813 (8)	0.32146 (13)	0.0703 (9)
C12	0.84822 (16)	0.5771 (10)	0.24301 (17)	0.0438 (10)
C13	0.89643 (17)	0.7151 (11)	0.26866 (18)	0.0563 (12)
H13	0.905122	0.738409	0.305052	0.068*
C14	0.93111 (17)	0.8166 (12)	0.2408 (2)	0.0614 (13)
H14	0.963255	0.907700	0.258215	0.074*
C15	0.91812 (16)	0.7830 (11)	0.18708 (19)	0.0515 (12)
C16	0.87094 (18)	0.6494 (11)	0.16089 (18)	0.0575 (12)
H16	0.862349	0.630215	0.124446	0.069*
C17	0.83643 (17)	0.5441 (11)	0.18891 (18)	0.0520 (12)
H17	0.804676	0.449286	0.171240	0.062*
Cl18	0.96251 (5)	0.9144 (4)	0.15236 (6)	0.0778 (4)
O19	0.73115 (15)	0.3394 (9)	0.33357 (14)	0.0678 (10)
Br20	0.54377 (2)	−0.42670 (12)	0.22329 (2)	0.06821 (19)
O21	0.70963 (11)	0.8529 (7)	0.44584 (11)	0.0543 (8)
C22	0.72238 (19)	1.0222 (11)	0.49411 (17)	0.0510 (12)
C23	0.6799 (2)	1.0408 (11)	0.51387 (17)	0.0540 (12)
C24	0.63657 (18)	0.8860 (10)	0.47749 (17)	0.0481 (11)
C25	0.58370 (18)	0.8345 (10)	0.47435 (18)	0.0537 (12)
H25	0.568715	0.905525	0.500961	0.064*
C26	0.55481 (17)	0.6758 (11)	0.43063 (19)	0.0527 (12)
C27	0.57635 (19)	0.5631 (11)	0.39031 (18)	0.0589 (13)
H27	0.555187	0.455037	0.361263	0.071*
C28	0.62855 (18)	0.6108 (11)	0.39319 (18)	0.0571 (12)
H28	0.643551	0.534760	0.366871	0.069*
C29	0.65764 (18)	0.7764 (11)	0.43690 (17)	0.0499 (11)
C30	0.77303 (19)	1.1543 (11)	0.51808 (19)	0.0567 (13)
O31	0.77683 (13)	1.2897 (9)	0.56258 (13)	0.0736 (10)
C32	0.81848 (18)	1.1521 (11)	0.49538 (18)	0.0541 (12)
C33	0.8658 (2)	1.2824 (12)	0.52436 (19)	0.0662 (14)
H33	0.867985	1.366531	0.557867	0.079*
C34	0.9090 (2)	1.2900 (14)	0.5049 (2)	0.0784 (16)
H34	0.940408	1.375615	0.525226	0.094*
C35	0.90609 (19)	1.1710 (13)	0.4553 (2)	0.0669 (14)
C36	0.8598 (2)	1.0437 (13)	0.4251 (2)	0.0691 (14)
H36	0.857813	0.964976	0.391294	0.083*
C37	0.81681 (19)	1.0340 (11)	0.44501 (19)	0.0631 (14)
H37	0.785654	0.946543	0.424512	0.076*
Cl38	0.96020 (6)	1.1822 (5)	0.42988 (7)	0.1069 (6)
O39	0.67804 (16)	1.1817 (9)	0.55988 (14)	0.0726 (11)
Br40	0.48242 (2)	0.59410 (13)	0.42371 (2)	0.07029 (19)
H19	0.7620 (18)	0.424 (12)	0.343 (2)	0.08 (2)*
H39	0.711 (2)	1.268 (17)	0.570 (3)	0.14 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0443 (16)	0.0494 (18)	0.0441 (19)	0.0027 (14)	0.0158 (14)	−0.0022 (14)
C2	0.045 (2)	0.047 (3)	0.034 (3)	0.007 (2)	0.013 (2)	0.003 (2)
C3	0.058 (3)	0.049 (3)	0.038 (3)	0.012 (2)	0.017 (2)	0.006 (2)
C4	0.043 (2)	0.042 (2)	0.047 (3)	0.012 (2)	0.014 (2)	0.007 (2)
C5	0.056 (3)	0.048 (3)	0.059 (3)	0.016 (2)	0.027 (3)	0.011 (2)
C6	0.050 (3)	0.037 (2)	0.068 (4)	0.007 (2)	0.021 (3)	0.005 (2)
C7	0.049 (3)	0.046 (3)	0.057 (3)	0.004 (2)	0.007 (2)	0.000 (2)
C8	0.052 (3)	0.045 (3)	0.051 (3)	0.003 (2)	0.017 (2)	0.000 (2)
C9	0.040 (2)	0.040 (3)	0.048 (3)	0.0076 (19)	0.012 (2)	0.003 (2)
C10	0.052 (3)	0.047 (3)	0.050 (3)	0.008 (2)	0.008 (2)	0.002 (2)
O11	0.073 (2)	0.095 (3)	0.042 (2)	−0.016 (2)	0.0125 (18)	−0.0123 (19)
C12	0.042 (2)	0.044 (2)	0.043 (3)	0.008 (2)	0.006 (2)	−0.001 (2)
C13	0.056 (3)	0.064 (3)	0.043 (3)	0.002 (3)	0.001 (3)	−0.005 (2)
C14	0.044 (3)	0.071 (3)	0.063 (4)	−0.005 (2)	0.002 (3)	−0.005 (3)
C15	0.045 (3)	0.049 (3)	0.059 (3)	0.002 (2)	0.010 (2)	0.002 (2)
C16	0.062 (3)	0.064 (3)	0.044 (3)	−0.008 (3)	0.008 (3)	−0.003 (2)
C17	0.045 (3)	0.058 (3)	0.051 (3)	−0.008 (2)	0.008 (2)	−0.002 (2)
Cl18	0.0611 (8)	0.0974 (10)	0.0795 (10)	−0.0114 (7)	0.0261 (7)	0.0049 (8)
O19	0.070 (2)	0.092 (3)	0.044 (2)	−0.007 (2)	0.0203 (19)	−0.0046 (19)
Br20	0.0535 (3)	0.0522 (3)	0.1076 (5)	0.0021 (2)	0.0364 (3)	0.0067 (3)
O21	0.0570 (19)	0.062 (2)	0.042 (2)	−0.0063 (16)	0.0098 (16)	−0.0054 (15)
C22	0.063 (3)	0.056 (3)	0.030 (3)	−0.005 (2)	0.006 (2)	−0.001 (2)
C23	0.076 (3)	0.055 (3)	0.029 (3)	−0.001 (3)	0.010 (3)	0.007 (2)
C24	0.060 (3)	0.045 (3)	0.039 (3)	−0.001 (2)	0.010 (2)	0.006 (2)
C25	0.070 (3)	0.047 (3)	0.047 (3)	0.004 (2)	0.020 (3)	0.007 (2)
C26	0.058 (3)	0.047 (3)	0.053 (3)	−0.003 (2)	0.013 (3)	0.013 (2)
C27	0.066 (3)	0.058 (3)	0.046 (3)	−0.008 (3)	0.004 (3)	0.000 (2)
C28	0.067 (3)	0.061 (3)	0.045 (3)	−0.004 (3)	0.016 (3)	−0.006 (2)
C29	0.062 (3)	0.049 (3)	0.038 (3)	−0.005 (2)	0.010 (2)	0.002 (2)
C30	0.070 (3)	0.051 (3)	0.041 (3)	0.000 (3)	0.000 (3)	0.003 (2)
O31	0.080 (2)	0.088 (3)	0.045 (2)	−0.006 (2)	0.0018 (19)	−0.0140 (19)
C32	0.063 (3)	0.050 (3)	0.043 (3)	−0.005 (2)	0.000 (3)	0.000 (2)
C33	0.074 (3)	0.066 (3)	0.049 (3)	−0.012 (3)	−0.001 (3)	−0.011 (3)
C34	0.062 (3)	0.090 (4)	0.074 (4)	−0.019 (3)	0.000 (3)	−0.010 (3)
C35	0.062 (3)	0.073 (4)	0.063 (4)	−0.012 (3)	0.011 (3)	−0.004 (3)
C36	0.068 (3)	0.086 (4)	0.051 (3)	−0.017 (3)	0.010 (3)	−0.014 (3)
C37	0.062 (3)	0.071 (3)	0.049 (3)	−0.016 (3)	0.000 (3)	−0.006 (3)
Cl38	0.0789 (10)	0.1375 (15)	0.1097 (13)	−0.0319 (10)	0.0336 (9)	−0.0211 (11)
O39	0.093 (3)	0.084 (3)	0.043 (2)	−0.009 (2)	0.021 (2)	−0.0099 (18)
Br40	0.0627 (3)	0.0649 (3)	0.0813 (4)	−0.0056 (3)	0.0145 (3)	0.0078 (3)

Geometric parameters (Å, º)

O1—C2	1.398 (4)	O21—C22	1.400 (5)
O1—C9	1.373 (4)	O21—C29	1.367 (5)
C2—C3	1.366 (5)	C22—C23	1.352 (6)
C2—C10	1.431 (6)	C22—C30	1.427 (6)
C3—C4	1.421 (6)	C23—C24	1.432 (6)
C3—O19	1.332 (5)	C23—O39	1.345 (5)
C4—C5	1.395 (5)	C24—C25	1.393 (6)
C4—C9	1.392 (5)	C24—C29	1.392 (6)
C5—H5	0.9300	C25—H25	0.9300
C5—C6	1.364 (6)	C25—C26	1.364 (6)
C6—C7	1.389 (6)	C26—C27	1.397 (6)
C6—Br20	1.899 (4)	C26—Br40	1.902 (4)
C7—H7	0.9300	C27—H27	0.9300
C7—C8	1.389 (5)	C27—C28	1.374 (6)
C8—H8	0.9300	C28—H28	0.9300
C8—C9	1.384 (5)	C28—C29	1.378 (6)
C10—O11	1.256 (5)	C30—O31	1.268 (5)
C10—C12	1.473 (6)	C30—C32	1.469 (6)
C12—C13	1.394 (5)	C32—C33	1.388 (6)
C12—C17	1.383 (5)	C32—C37	1.395 (6)
C13—H13	0.9300	C33—H33	0.9300
C13—C14	1.369 (6)	C33—C34	1.365 (6)
C14—H14	0.9300	C34—H34	0.9300
C14—C15	1.373 (6)	C34—C35	1.369 (6)
C15—C16	1.370 (6)	C35—C36	1.376 (6)
C15—Cl18	1.738 (5)	C35—Cl38	1.724 (5)
C16—H16	0.9300	C36—H36	0.9300
C16—C17	1.374 (6)	C36—C37	1.366 (6)
C17—H17	0.9300	C37—H37	0.9300
O19—H19	0.86 (5)	O39—H39	0.90 (6)
C9—O1—C2	105.2 (3)	C29—O21—C22	105.3 (3)
O1—C2—C10	124.8 (4)	O21—C22—C30	124.2 (4)
C3—C2—O1	110.2 (4)	C23—C22—O21	109.9 (4)
C3—C2—C10	125.0 (4)	C23—C22—C30	125.9 (4)
C2—C3—C4	108.0 (4)	C22—C23—C24	108.7 (4)
O19—C3—C2	126.6 (4)	O39—C23—C22	126.1 (4)
O19—C3—C4	125.3 (4)	O39—C23—C24	125.2 (5)
C5—C4—C3	135.4 (4)	C25—C24—C23	136.3 (5)
C9—C4—C3	104.8 (4)	C29—C24—C23	103.9 (4)
C9—C4—C5	119.8 (4)	C29—C24—C25	119.8 (4)
C4—C5—H5	121.4	C24—C25—H25	121.4
C6—C5—C4	117.2 (4)	C26—C25—C24	117.2 (4)
C6—C5—H5	121.4	C26—C25—H25	121.4
C5—C6—C7	122.8 (4)	C25—C26—C27	122.7 (4)
C5—C6—Br20	118.5 (4)	C25—C26—Br40	119.7 (4)
C7—C6—Br20	118.8 (4)	C27—C26—Br40	117.7 (4)
C6—C7—H7	119.5	C26—C27—H27	119.7
C8—C7—C6	121.0 (4)	C28—C27—C26	120.6 (4)
C8—C7—H7	119.5	C28—C27—H27	119.7
C7—C8—H8	122.0	C27—C28—H28	121.5
C9—C8—C7	116.0 (4)	C27—C28—C29	116.9 (4)
C9—C8—H8	122.0	C29—C28—H28	121.5
O1—C9—C4	111.8 (4)	O21—C29—C24	112.1 (4)
O1—C9—C8	125.0 (4)	O21—C29—C28	125.0 (4)
C8—C9—C4	123.2 (4)	C28—C29—C24	122.8 (4)
C2—C10—C12	125.8 (4)	C22—C30—C32	126.1 (4)
O11—C10—C2	114.6 (4)	O31—C30—C22	114.3 (5)
O11—C10—C12	119.6 (4)	O31—C30—C32	119.6 (4)
C13—C12—C10	118.5 (4)	C33—C32—C30	119.3 (4)
C17—C12—C10	123.0 (4)	C33—C32—C37	117.1 (5)
C17—C12—C13	118.4 (4)	C37—C32—C30	123.6 (4)
C12—C13—H13	119.7	C32—C33—H33	119.2
C14—C13—C12	120.7 (4)	C34—C33—C32	121.6 (5)
C14—C13—H13	119.7	C34—C33—H33	119.2
C13—C14—H14	120.2	C33—C34—H34	120.1
C13—C14—C15	119.6 (4)	C33—C34—C35	119.8 (5)
C15—C14—H14	120.2	C35—C34—H34	120.1
C14—C15—Cl18	119.0 (4)	C34—C35—C36	120.4 (5)
C16—C15—C14	121.0 (4)	C34—C35—Cl38	120.4 (4)
C16—C15—Cl18	120.1 (4)	C36—C35—Cl38	119.2 (4)
C15—C16—H16	120.3	C35—C36—H36	120.3
C15—C16—C17	119.4 (4)	C37—C36—C35	119.4 (5)
C17—C16—H16	120.3	C37—C36—H36	120.3
C12—C17—H17	119.5	C32—C37—H37	119.2
C16—C17—C12	121.0 (4)	C36—C37—C32	121.6 (4)
C16—C17—H17	119.5	C36—C37—H37	119.2
C3—O19—H19	102 (4)	C23—O39—H39	99 (4)
O1—C2—C3—C4	−1.0 (4)	O21—C22—C23—C24	−1.3 (5)
O1—C2—C3—O19	179.5 (4)	O21—C22—C23—O39	179.0 (4)
O1—C2—C10—O11	−176.3 (4)	O21—C22—C30—O31	−177.9 (4)
O1—C2—C10—C12	5.1 (6)	O21—C22—C30—C32	3.6 (7)
C2—O1—C9—C4	−0.1 (4)	C22—O21—C29—C24	−0.6 (5)
C2—O1—C9—C8	−179.6 (4)	C22—O21—C29—C28	179.4 (4)
C2—C3—C4—C5	−178.8 (4)	C22—C23—C24—C25	−177.8 (5)
C2—C3—C4—C9	0.8 (4)	C22—C23—C24—C29	0.9 (5)
C2—C10—C12—C13	−169.9 (4)	C22—C30—C32—C33	−178.1 (4)
C2—C10—C12—C17	12.6 (6)	C22—C30—C32—C37	3.8 (7)
C3—C2—C10—O11	4.6 (6)	C23—C22—C30—O31	2.3 (7)
C3—C2—C10—C12	−174.0 (4)	C23—C22—C30—C32	−176.2 (4)
C3—C4—C5—C6	179.7 (4)	C23—C24—C25—C26	178.5 (5)
C3—C4—C9—O1	−0.5 (4)	C23—C24—C29—O21	−0.1 (5)
C3—C4—C9—C8	179.1 (4)	C23—C24—C29—C28	179.9 (4)
C4—C5—C6—C7	1.0 (6)	C24—C25—C26—C27	0.7 (6)
C4—C5—C6—Br20	−179.6 (3)	C24—C25—C26—Br40	179.6 (3)
C5—C4—C9—O1	179.3 (3)	C25—C24—C29—O21	178.8 (4)
C5—C4—C9—C8	−1.2 (6)	C25—C24—C29—C28	−1.2 (7)
C5—C6—C7—C8	−1.0 (7)	C25—C26—C27—C28	−0.3 (7)
C6—C7—C8—C9	−0.1 (6)	C26—C27—C28—C29	−0.8 (7)
C7—C8—C9—O1	−179.4 (3)	C27—C28—C29—O21	−178.4 (4)
C7—C8—C9—C4	1.2 (6)	C27—C28—C29—C24	1.6 (7)
C9—O1—C2—C3	0.7 (4)	C29—O21—C22—C23	1.1 (5)
C9—O1—C2—C10	−178.5 (4)	C29—O21—C22—C30	−178.7 (4)
C9—C4—C5—C6	0.1 (6)	C29—C24—C25—C26	0.0 (6)
C10—C2—C3—C4	178.2 (4)	C30—C22—C23—C24	178.6 (4)
C10—C2—C3—O19	−1.3 (7)	C30—C22—C23—O39	−1.2 (7)
C10—C12—C13—C14	−177.4 (4)	C30—C32—C33—C34	−179.2 (5)
C10—C12—C17—C16	176.6 (4)	C30—C32—C37—C36	178.5 (4)
O11—C10—C12—C13	11.6 (6)	O31—C30—C32—C33	3.5 (7)
O11—C10—C12—C17	−166.0 (4)	O31—C30—C32—C37	−174.6 (4)
C12—C13—C14—C15	0.2 (7)	C32—C33—C34—C35	0.9 (8)
C13—C12—C17—C16	−1.0 (6)	C33—C32—C37—C36	0.4 (7)
C13—C14—C15—C16	0.0 (7)	C33—C34—C35—C36	0.0 (8)
C13—C14—C15—Cl18	179.8 (4)	C33—C34—C35—Cl38	179.4 (4)
C14—C15—C16—C17	−0.8 (7)	C34—C35—C36—C37	−0.6 (8)
C15—C16—C17—C12	1.3 (7)	C35—C36—C37—C32	0.4 (8)
C17—C12—C13—C14	0.3 (6)	C37—C32—C33—C34	−1.0 (7)
Cl18—C15—C16—C17	179.5 (3)	Cl38—C35—C36—C37	180.0 (4)
O19—C3—C4—C5	0.7 (8)	O39—C23—C24—C25	2.0 (8)
O19—C3—C4—C9	−179.6 (4)	O39—C23—C24—C29	−179.4 (4)
Br20—C6—C7—C8	179.6 (3)	Br40—C26—C27—C28	−179.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O11	0.86 (5)	1.87 (5)	2.631 (5)	147 (5)
C17—H17···O1	0.93	2.29	2.951 (5)	128
O39—H39···O31	0.91 (6)	1.80 (6)	2.627 (6)	150 (7)
C37—H37···O21	0.93	2.25	2.926 (6)	129
C36—H36···O11	0.93	2.40	3.235 (6)	149
C8—H8···O39^i	0.93	2.67	3.434 (6)	140

Symmetry code: (i) x, −y+1/2, z−1/2.

(5-Bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone (4c)

Crystal data

C15H8Br2O3	Z = 2
Mr = 396.03	F(000) = 384
Triclinic, P1	Dx = 1.887 Mg m^−3
a = 7.0725 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0884 (5) Å	Cell parameters from 3969 reflections
c = 14.6069 (8) Å	θ = 2.9–25.0°
α = 92.230 (5)°	µ = 5.82 mm^−1
β = 103.091 (5)°	T = 294 K
γ = 101.219 (6)°	Plate, yellow
V = 696.98 (8) Å^3	0.35 × 0.15 × 0.05 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Eos detector	2840 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1867 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.046
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −8→8
Tmin = 0.523, Tmax = 1.000	l = −18→18
14183 measured reflections

Refinement

Refinement on F^2	0 restraints
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) = 0.109	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.4345P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2840 reflections	Δρmax = 0.44 e Å^−3
185 parameters	Δρmin = −0.40 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
O1	0.2698 (4)	0.5503 (4)	0.38600 (19)	0.0488 (7)
C2	0.2236 (6)	0.3699 (6)	0.4205 (3)	0.0451 (10)
C3	0.1893 (6)	0.2269 (6)	0.3496 (3)	0.0492 (10)
C4	0.2133 (6)	0.3147 (6)	0.2657 (3)	0.0467 (10)
C5	0.1950 (6)	0.2465 (7)	0.1721 (3)	0.0538 (11)
H5	0.162112	0.115376	0.152601	0.065*
C6	0.2283 (6)	0.3842 (8)	0.1110 (3)	0.0603 (13)
C7	0.2745 (7)	0.5815 (8)	0.1380 (3)	0.0644 (13)
H7	0.294088	0.668302	0.093245	0.077*
C8	0.2919 (7)	0.6517 (7)	0.2302 (3)	0.0583 (12)
H8	0.322333	0.783073	0.249141	0.070*
C9	0.2605 (6)	0.5113 (6)	0.2925 (3)	0.0470 (10)
C10	0.2117 (6)	0.3412 (6)	0.5157 (3)	0.0471 (10)
O11	0.1679 (5)	0.1689 (4)	0.5325 (2)	0.0672 (9)
C12	0.2445 (5)	0.4957 (6)	0.5920 (3)	0.0432 (10)
C13	0.2243 (6)	0.4393 (7)	0.6802 (3)	0.0528 (11)
H13	0.190559	0.308580	0.688378	0.063*
C14	0.2529 (6)	0.5720 (7)	0.7550 (3)	0.0562 (12)
H14	0.239823	0.532483	0.813584	0.067*
C15	0.3015 (6)	0.7652 (7)	0.7422 (3)	0.0516 (11)
C16	0.3218 (6)	0.8272 (7)	0.6564 (3)	0.0538 (11)
H16	0.354165	0.958359	0.648961	0.065*
C17	0.2934 (6)	0.6921 (6)	0.5815 (3)	0.0485 (10)
H17	0.307233	0.732746	0.523116	0.058*
Br18	0.34142 (8)	0.94907 (8)	0.84645 (4)	0.0757 (2)
O19	0.1385 (5)	0.0365 (5)	0.3552 (3)	0.0671 (9)
Br20	0.20857 (10)	0.30111 (10)	−0.01643 (4)	0.0906 (3)
H19	0.127 (9)	0.030 (8)	0.411 (4)	0.10 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0533 (18)	0.0470 (17)	0.0475 (16)	0.0062 (14)	0.0175 (13)	0.0085 (13)
C2	0.044 (2)	0.044 (3)	0.048 (2)	0.008 (2)	0.0135 (19)	0.009 (2)
C3	0.051 (3)	0.048 (3)	0.053 (3)	0.011 (2)	0.020 (2)	0.010 (2)
C4	0.038 (2)	0.053 (3)	0.052 (3)	0.011 (2)	0.0147 (19)	0.009 (2)
C5	0.051 (3)	0.056 (3)	0.055 (3)	0.010 (2)	0.015 (2)	0.002 (2)
C6	0.054 (3)	0.084 (4)	0.044 (2)	0.016 (3)	0.012 (2)	0.006 (3)
C7	0.064 (3)	0.075 (4)	0.056 (3)	0.011 (3)	0.019 (2)	0.021 (3)
C8	0.067 (3)	0.057 (3)	0.052 (3)	0.007 (2)	0.021 (2)	0.014 (2)
C9	0.040 (2)	0.057 (3)	0.046 (2)	0.008 (2)	0.0142 (19)	0.007 (2)
C10	0.045 (3)	0.049 (3)	0.048 (2)	0.010 (2)	0.0123 (19)	0.013 (2)
O11	0.099 (3)	0.0453 (19)	0.0565 (19)	0.0070 (18)	0.0227 (17)	0.0145 (15)
C12	0.036 (2)	0.052 (3)	0.043 (2)	0.010 (2)	0.0116 (18)	0.013 (2)
C13	0.056 (3)	0.054 (3)	0.053 (3)	0.011 (2)	0.018 (2)	0.018 (2)
C14	0.056 (3)	0.069 (3)	0.047 (3)	0.011 (2)	0.018 (2)	0.014 (2)
C15	0.046 (3)	0.060 (3)	0.049 (3)	0.008 (2)	0.013 (2)	0.002 (2)
C16	0.055 (3)	0.047 (3)	0.058 (3)	0.006 (2)	0.013 (2)	0.008 (2)
C17	0.050 (3)	0.052 (3)	0.044 (2)	0.009 (2)	0.0131 (19)	0.011 (2)
Br18	0.0838 (4)	0.0774 (4)	0.0631 (3)	0.0050 (3)	0.0248 (3)	−0.0112 (3)
O19	0.102 (3)	0.046 (2)	0.059 (2)	0.0128 (18)	0.031 (2)	0.0083 (16)
Br20	0.1167 (5)	0.1131 (5)	0.0462 (3)	0.0303 (4)	0.0227 (3)	0.0072 (3)

Geometric parameters (Å, º)

O1—C2	1.399 (5)	C7—C8	1.387 (6)
O1—C9	1.368 (5)	C8—C9	1.394 (6)
C2—C3	1.367 (6)	C10—O11	1.248 (5)
C2—C10	1.432 (5)	C10—C12	1.478 (6)
C3—C4	1.425 (5)	C12—C13	1.394 (5)
C3—O19	1.338 (5)	C12—C17	1.391 (6)
C4—C5	1.400 (6)	C13—C14	1.365 (6)
C4—C9	1.387 (6)	C14—C15	1.376 (6)
C5—C6	1.370 (6)	C15—C16	1.372 (6)
C6—C7	1.393 (7)	C15—Br18	1.899 (4)
C6—Br20	1.896 (4)	C16—C17	1.379 (6)
C9—O1—C2	105.3 (3)	O1—C9—C4	112.3 (3)
O1—C2—C10	124.7 (4)	O1—C9—C8	124.3 (4)
C3—C2—O1	109.8 (3)	C4—C9—C8	123.4 (4)
C3—C2—C10	125.5 (4)	C2—C10—C12	125.6 (4)
C2—C3—C4	108.2 (4)	O11—C10—C2	114.9 (4)
O19—C3—C2	127.2 (4)	O11—C10—C12	119.5 (4)
O19—C3—C4	124.6 (4)	C13—C12—C10	117.3 (4)
C5—C4—C3	135.0 (4)	C17—C12—C10	124.5 (3)
C9—C4—C3	104.4 (4)	C17—C12—C13	118.2 (4)
C9—C4—C5	120.6 (4)	C14—C13—C12	121.3 (4)
C6—C5—C4	116.2 (4)	C13—C14—C15	119.0 (4)
C5—C6—C7	123.1 (4)	C14—C15—Br18	118.7 (3)
C5—C6—Br20	118.2 (4)	C16—C15—C14	121.6 (4)
C7—C6—Br20	118.7 (4)	C16—C15—Br18	119.6 (3)
C8—C7—C6	121.5 (4)	C15—C16—C17	119.0 (4)
C7—C8—C9	115.2 (5)	C16—C17—C12	120.8 (4)
O1—C2—C3—C4	0.0 (5)	C7—C8—C9—C4	−0.6 (6)
O1—C2—C3—O19	−179.0 (4)	C9—O1—C2—C3	0.5 (4)
O1—C2—C10—O11	179.8 (4)	C9—O1—C2—C10	−178.7 (4)
O1—C2—C10—C12	0.5 (6)	C9—C4—C5—C6	0.6 (6)
C2—O1—C9—C4	−0.8 (4)	C10—C2—C3—C4	179.2 (4)
C2—O1—C9—C8	178.3 (4)	C10—C2—C3—O19	0.2 (7)
C2—C3—C4—C5	−178.7 (4)	C10—C12—C13—C14	179.6 (4)
C2—C3—C4—C9	−0.4 (4)	C10—C12—C17—C16	−179.9 (4)
C2—C10—C12—C13	179.3 (4)	O11—C10—C12—C13	0.0 (6)
C2—C10—C12—C17	−0.6 (6)	O11—C10—C12—C17	−179.9 (4)
C3—C2—C10—O11	0.7 (6)	C12—C13—C14—C15	0.4 (6)
C3—C2—C10—C12	−178.6 (4)	C13—C12—C17—C16	0.2 (6)
C3—C4—C5—C6	178.7 (4)	C13—C14—C15—C16	0.0 (6)
C3—C4—C9—O1	0.8 (4)	C13—C14—C15—Br18	−179.9 (3)
C3—C4—C9—C8	−178.4 (4)	C14—C15—C16—C17	−0.3 (6)
C4—C5—C6—C7	−1.1 (6)	C15—C16—C17—C12	0.2 (6)
C4—C5—C6—Br20	179.3 (3)	C17—C12—C13—C14	−0.5 (6)
C5—C4—C9—O1	179.4 (3)	Br18—C15—C16—C17	179.7 (3)
C5—C4—C9—C8	0.2 (6)	O19—C3—C4—C5	0.3 (7)
C5—C6—C7—C8	0.7 (7)	O19—C3—C4—C9	178.6 (4)
C6—C7—C8—C9	0.2 (7)	Br20—C6—C7—C8	−179.7 (3)
C7—C8—C9—O1	−179.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O11	0.84 (6)	1.93 (6)	2.669 (5)	146 (5)
C17—H17···O1	0.93	2.28	2.948 (5)	129
O19—H19···O11^i	0.84 (6)	2.60 (6)	3.174 (5)	127
C14—H14···Br20^ii	0.93	3.05	3.959 (5)	165
C16—H16···O11^iii	0.93	2.61	3.287 (6)	130

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

(4-Bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone (4h)

Crystal data

C15H8BrIO3	F(000) = 3360
Mr = 443.02	Dx = 2.087 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 26.4214 (8) Å	Cell parameters from 11835 reflections
b = 4.76309 (13) Å	θ = 2.7–27.2°
c = 46.6213 (14) Å	µ = 5.11 mm^−1
β = 106.034 (3)°	T = 293 K
V = 5638.9 (3) Å^3	Needle, yellow
Z = 16	0.35 × 0.15 × 0.05 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Eos detector	5733 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4448 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.7°
ω scans	h = −32→33
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	k = −5→5
Tmin = 0.582, Tmax = 1.000	l = −58→58
30966 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 38.6563P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
5733 reflections	Δρmax = 1.78 e Å^−3
369 parameters	Δρmin = −1.21 e Å^−3
2 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
O1	0.31437 (17)	−0.1296 (9)	0.62348 (9)	0.0509 (10)
C2	0.3471 (2)	0.0161 (13)	0.60926 (12)	0.0440 (14)
C3	0.3360 (2)	−0.0703 (13)	0.58016 (13)	0.0442 (14)
C4	0.2954 (2)	−0.2773 (12)	0.57509 (12)	0.0423 (13)
C5	0.2670 (2)	−0.4364 (13)	0.55069 (14)	0.0501 (15)
H5	0.274146	−0.425178	0.532280	0.060*
C6	0.2279 (3)	−0.6110 (14)	0.55498 (14)	0.0519 (16)
C7	0.2174 (3)	−0.6343 (15)	0.58299 (16)	0.0606 (18)
H7	0.191032	−0.755200	0.585119	0.073*
C8	0.2457 (3)	−0.4804 (15)	0.60729 (15)	0.0592 (18)
H8	0.239390	−0.496240	0.625887	0.071*
C9	0.2837 (3)	−0.3023 (13)	0.60254 (14)	0.0489 (15)
C10	0.3842 (2)	0.2278 (13)	0.62289 (13)	0.0426 (13)
O11	0.40906 (18)	0.3384 (10)	0.60636 (9)	0.0561 (11)
C12	0.3956 (2)	0.3180 (12)	0.65444 (13)	0.0434 (13)
C13	0.4331 (3)	0.5229 (15)	0.66462 (15)	0.0568 (17)
H13	0.449736	0.602010	0.651387	0.068*
C14	0.4469 (3)	0.6151 (15)	0.69416 (15)	0.0577 (17)
H14	0.473533	0.746849	0.700905	0.069*
C15	0.4200 (3)	0.5055 (14)	0.71317 (13)	0.0505 (15)
C16	0.3822 (3)	0.3006 (14)	0.70382 (14)	0.0536 (16)
H16	0.365082	0.225725	0.717047	0.064*
C17	0.3699 (3)	0.2079 (14)	0.67478 (15)	0.0533 (16)
H17	0.344307	0.070224	0.668447	0.064*
Br18	0.43363 (3)	0.64613 (18)	0.75258 (2)	0.0687 (2)
O19	0.3584 (2)	0.0240 (12)	0.55955 (10)	0.0569 (12)
I20	0.18141 (2)	−0.84287 (11)	0.51858 (2)	0.06610 (17)
O21	0.59407 (16)	0.3302 (9)	0.61452 (9)	0.0479 (10)
C22	0.5739 (2)	0.3006 (13)	0.63934 (13)	0.0447 (14)
C23	0.5344 (2)	0.1034 (13)	0.63325 (13)	0.0450 (14)
C24	0.5269 (2)	0.0073 (12)	0.60347 (13)	0.0448 (14)
C25	0.4916 (2)	−0.1762 (14)	0.58424 (13)	0.0481 (14)
H25	0.466170	−0.274141	0.590511	0.058*
C26	0.4964 (3)	−0.2045 (14)	0.55608 (14)	0.0507 (15)
C27	0.5355 (3)	−0.0663 (15)	0.54646 (14)	0.0560 (16)
H27	0.538039	−0.097817	0.527223	0.067*
C28	0.5702 (3)	0.1147 (15)	0.56484 (15)	0.0571 (17)
H28	0.596072	0.208781	0.558524	0.069*
C29	0.5646 (2)	0.1500 (13)	0.59361 (13)	0.0459 (14)
C30	0.5924 (2)	0.4426 (14)	0.66678 (13)	0.0473 (14)
O31	0.57006 (18)	0.3832 (11)	0.68662 (10)	0.0601 (12)
C32	0.6364 (2)	0.6516 (13)	0.67412 (13)	0.0456 (14)
C33	0.6541 (3)	0.7459 (17)	0.70387 (15)	0.066 (2)
H33	0.637978	0.682757	0.718059	0.079*
C34	0.6958 (3)	0.9338 (17)	0.71181 (16)	0.069 (2)
H34	0.707602	0.996950	0.731405	0.082*
C35	0.7195 (2)	1.0266 (14)	0.69098 (15)	0.0523 (16)
C36	0.7020 (3)	0.9403 (15)	0.66182 (16)	0.0592 (17)
H36	0.717881	1.008713	0.647729	0.071*
C37	0.6611 (3)	0.7523 (14)	0.65349 (14)	0.0504 (15)
H37	0.649775	0.691805	0.633777	0.061*
Br38	0.77726 (3)	1.27828 (18)	0.70198 (2)	0.0785 (3)
O39	0.50813 (19)	0.0169 (11)	0.65218 (11)	0.0583 (12)
I40	0.43898 (2)	−0.44310 (11)	0.52517 (2)	0.06144 (16)
H39	0.521 (4)	0.109 (19)	0.6664 (11)	0.14 (5)*
H19	0.372 (4)	0.16 (2)	0.566 (2)	0.12 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.063 (3)	0.050 (3)	0.040 (2)	−0.011 (2)	0.016 (2)	−0.0027 (19)
C2	0.050 (3)	0.047 (4)	0.035 (3)	0.001 (3)	0.012 (3)	0.002 (3)
C3	0.046 (3)	0.043 (3)	0.044 (3)	0.010 (3)	0.012 (3)	0.008 (3)
C4	0.047 (3)	0.040 (3)	0.038 (3)	0.008 (3)	0.008 (3)	0.003 (2)
C5	0.052 (4)	0.048 (4)	0.047 (3)	0.014 (3)	0.009 (3)	0.006 (3)
C6	0.050 (4)	0.045 (4)	0.052 (4)	0.003 (3)	0.000 (3)	−0.002 (3)
C7	0.063 (4)	0.053 (4)	0.064 (4)	−0.009 (3)	0.014 (4)	0.001 (3)
C8	0.075 (5)	0.055 (4)	0.051 (4)	−0.013 (4)	0.022 (3)	−0.004 (3)
C9	0.058 (4)	0.041 (4)	0.048 (3)	0.000 (3)	0.014 (3)	−0.001 (3)
C10	0.047 (3)	0.041 (3)	0.043 (3)	0.006 (3)	0.017 (3)	0.007 (3)
O11	0.060 (3)	0.063 (3)	0.047 (2)	−0.010 (2)	0.016 (2)	0.003 (2)
C12	0.041 (3)	0.039 (3)	0.050 (3)	−0.002 (3)	0.013 (3)	0.003 (3)
C13	0.058 (4)	0.059 (4)	0.055 (4)	−0.011 (3)	0.020 (3)	0.000 (3)
C14	0.061 (4)	0.058 (4)	0.054 (4)	−0.015 (3)	0.017 (3)	−0.006 (3)
C15	0.061 (4)	0.047 (4)	0.041 (3)	0.005 (3)	0.009 (3)	−0.001 (3)
C16	0.061 (4)	0.058 (4)	0.046 (3)	−0.009 (3)	0.021 (3)	0.000 (3)
C17	0.058 (4)	0.048 (4)	0.055 (4)	−0.010 (3)	0.017 (3)	0.000 (3)
Br18	0.0813 (5)	0.0782 (5)	0.0436 (4)	−0.0039 (4)	0.0122 (3)	−0.0089 (3)
O19	0.061 (3)	0.070 (3)	0.041 (2)	−0.005 (3)	0.016 (2)	−0.003 (2)
I20	0.0611 (3)	0.0597 (3)	0.0616 (3)	0.0046 (2)	−0.0096 (2)	−0.0056 (2)
O21	0.047 (2)	0.052 (3)	0.047 (2)	−0.009 (2)	0.0178 (19)	−0.005 (2)
C22	0.046 (3)	0.045 (4)	0.042 (3)	0.000 (3)	0.011 (3)	0.003 (3)
C23	0.044 (3)	0.047 (4)	0.046 (3)	0.001 (3)	0.016 (3)	0.008 (3)
C24	0.047 (3)	0.038 (3)	0.048 (3)	0.001 (3)	0.011 (3)	0.005 (3)
C25	0.045 (3)	0.049 (4)	0.047 (3)	−0.001 (3)	0.009 (3)	0.002 (3)
C26	0.050 (4)	0.045 (4)	0.050 (4)	0.001 (3)	0.003 (3)	−0.005 (3)
C27	0.061 (4)	0.063 (4)	0.045 (3)	−0.004 (3)	0.016 (3)	−0.006 (3)
C28	0.062 (4)	0.062 (4)	0.054 (4)	−0.009 (3)	0.025 (3)	−0.010 (3)
C29	0.047 (3)	0.044 (3)	0.047 (3)	−0.005 (3)	0.015 (3)	−0.003 (3)
C30	0.046 (3)	0.049 (4)	0.046 (3)	0.005 (3)	0.012 (3)	0.003 (3)
O31	0.065 (3)	0.072 (3)	0.046 (2)	−0.007 (2)	0.020 (2)	0.003 (2)
C32	0.044 (3)	0.042 (3)	0.048 (3)	0.003 (3)	0.008 (3)	−0.004 (3)
C33	0.079 (5)	0.076 (5)	0.045 (4)	−0.009 (4)	0.021 (4)	−0.015 (4)
C34	0.069 (5)	0.080 (5)	0.050 (4)	−0.005 (4)	0.006 (4)	−0.030 (4)
C35	0.044 (3)	0.049 (4)	0.061 (4)	0.006 (3)	0.011 (3)	−0.014 (3)
C36	0.059 (4)	0.055 (4)	0.068 (4)	−0.010 (3)	0.025 (4)	−0.010 (3)
C37	0.054 (4)	0.053 (4)	0.045 (3)	−0.004 (3)	0.016 (3)	−0.007 (3)
Br38	0.0571 (4)	0.0704 (5)	0.1037 (6)	−0.0097 (4)	0.0152 (4)	−0.0352 (5)
O39	0.066 (3)	0.060 (3)	0.051 (3)	−0.012 (2)	0.019 (2)	0.004 (2)
I40	0.0614 (3)	0.0613 (3)	0.0563 (3)	−0.0061 (2)	0.0073 (2)	−0.0138 (2)

Geometric parameters (Å, º)

O1—C2	1.410 (7)	O21—C22	1.409 (7)
O1—C9	1.360 (7)	O21—C29	1.369 (7)
C2—C3	1.370 (8)	C22—C23	1.373 (9)
C2—C10	1.427 (9)	C22—C30	1.410 (9)
C3—C4	1.427 (9)	C23—C24	1.423 (8)
C3—O19	1.339 (7)	C23—O39	1.330 (7)
C4—C5	1.400 (9)	C24—C25	1.404 (9)
C4—C9	1.402 (8)	C24—C29	1.385 (8)
C5—H5	0.9300	C25—H25	0.9300
C5—C6	1.383 (9)	C25—C26	1.360 (9)
C6—C7	1.412 (10)	C26—C27	1.399 (9)
C6—I20	2.111 (6)	C26—I40	2.112 (6)
C7—H7	0.9300	C27—H27	0.9300
C7—C8	1.383 (9)	C27—C28	1.373 (9)
C8—H8	0.9300	C28—H28	0.9300
C8—C9	1.379 (9)	C28—C29	1.400 (9)
C10—O11	1.258 (7)	C30—O31	1.260 (7)
C10—C12	1.481 (8)	C30—C32	1.495 (9)
C12—C13	1.379 (9)	C32—C33	1.409 (9)
C12—C17	1.410 (8)	C32—C37	1.388 (9)
C13—H13	0.9300	C33—H33	0.9300
C13—C14	1.395 (9)	C33—C34	1.388 (11)
C14—H14	0.9300	C34—H34	0.9300
C14—C15	1.383 (9)	C34—C35	1.367 (10)
C15—C16	1.378 (9)	C35—C36	1.372 (9)
C15—Br18	1.894 (6)	C35—Br38	1.897 (7)
C16—H16	0.9300	C36—H36	0.9300
C16—C17	1.375 (9)	C36—C37	1.376 (9)
C17—H17	0.9300	C37—H37	0.9300
O19—H19	0.78 (11)	O39—H39	0.79 (2)
C9—O1—C2	106.3 (4)	C29—O21—C22	104.6 (4)
O1—C2—C10	125.0 (5)	O21—C22—C30	125.5 (5)
C3—C2—O1	109.0 (5)	C23—C22—O21	109.7 (5)
C3—C2—C10	126.0 (6)	C23—C22—C30	124.7 (6)
C2—C3—C4	108.6 (5)	C22—C23—C24	108.4 (5)
O19—C3—C2	126.4 (6)	O39—C23—C22	125.5 (6)
O19—C3—C4	125.1 (6)	O39—C23—C24	126.1 (6)
C5—C4—C3	135.9 (6)	C25—C24—C23	135.4 (6)
C5—C4—C9	119.5 (6)	C29—C24—C23	104.3 (5)
C9—C4—C3	104.6 (5)	C29—C24—C25	120.3 (6)
C4—C5—H5	121.2	C24—C25—H25	121.4
C6—C5—C4	117.5 (6)	C26—C25—C24	117.2 (6)
C6—C5—H5	121.2	C26—C25—H25	121.4
C5—C6—C7	121.8 (6)	C25—C26—C27	122.4 (6)
C5—C6—I20	119.4 (5)	C25—C26—I40	118.2 (5)
C7—C6—I20	118.9 (5)	C27—C26—I40	119.3 (5)
C6—C7—H7	119.5	C26—C27—H27	119.3
C8—C7—C6	121.1 (7)	C28—C27—C26	121.4 (6)
C8—C7—H7	119.5	C28—C27—H27	119.3
C7—C8—H8	121.7	C27—C28—H28	121.8
C9—C8—C7	116.6 (6)	C27—C28—C29	116.3 (6)
C9—C8—H8	121.7	C29—C28—H28	121.8
O1—C9—C4	111.5 (5)	O21—C29—C24	113.1 (5)
O1—C9—C8	124.9 (6)	O21—C29—C28	124.5 (6)
C8—C9—C4	123.6 (6)	C24—C29—C28	122.4 (6)
C2—C10—C12	125.0 (5)	C22—C30—C32	125.5 (6)
O11—C10—C2	115.7 (5)	O31—C30—C22	116.2 (6)
O11—C10—C12	119.3 (6)	O31—C30—C32	118.3 (6)
C13—C12—C10	118.4 (5)	C33—C32—C30	117.6 (6)
C13—C12—C17	117.7 (6)	C37—C32—C30	123.7 (5)
C17—C12—C10	123.8 (6)	C37—C32—C33	118.7 (6)
C12—C13—H13	119.0	C32—C33—H33	120.3
C12—C13—C14	122.0 (6)	C34—C33—C32	119.4 (7)
C14—C13—H13	119.0	C34—C33—H33	120.3
C13—C14—H14	120.9	C33—C34—H34	119.8
C15—C14—C13	118.3 (6)	C35—C34—C33	120.3 (6)
C15—C14—H14	120.9	C35—C34—H34	119.8
C14—C15—Br18	119.6 (5)	C34—C35—C36	120.8 (6)
C16—C15—C14	121.4 (6)	C34—C35—Br38	120.3 (5)
C16—C15—Br18	118.9 (5)	C36—C35—Br38	118.8 (5)
C15—C16—H16	120.3	C35—C36—H36	120.1
C17—C16—C15	119.4 (6)	C35—C36—C37	119.9 (7)
C17—C16—H16	120.3	C37—C36—H36	120.1
C12—C17—H17	119.4	C32—C37—H37	119.6
C16—C17—C12	121.1 (6)	C36—C37—C32	120.8 (6)
C16—C17—H17	119.4	C36—C37—H37	119.6
C3—O19—H19	104 (8)	C23—O39—H39	101 (4)
O1—C2—C3—C4	−0.3 (7)	O21—C22—C23—C24	−2.1 (7)
O1—C2—C3—O19	178.9 (6)	O21—C22—C23—O39	177.5 (6)
O1—C2—C10—O11	−178.5 (5)	O21—C22—C30—O31	−178.4 (6)
O1—C2—C10—C12	2.8 (10)	O21—C22—C30—C32	0.7 (10)
C2—O1—C9—C4	0.5 (7)	C22—O21—C29—C24	0.0 (7)
C2—O1—C9—C8	−179.4 (6)	C22—O21—C29—C28	178.5 (6)
C2—C3—C4—C5	178.4 (7)	C22—C23—C24—C25	−175.9 (7)
C2—C3—C4—C9	0.6 (7)	C22—C23—C24—C29	2.0 (7)
C2—C10—C12—C13	179.0 (6)	C22—C30—C32—C33	−172.1 (6)
C2—C10—C12—C17	−1.4 (10)	C22—C30—C32—C37	6.6 (10)
C3—C2—C10—O11	−1.4 (9)	C23—C22—C30—O31	−1.0 (9)
C3—C2—C10—C12	179.9 (6)	C23—C22—C30—C32	178.1 (6)
C3—C4—C5—C6	−177.0 (6)	C23—C24—C25—C26	177.4 (7)
C3—C4—C9—O1	−0.7 (7)	C23—C24—C29—O21	−1.2 (7)
C3—C4—C9—C8	179.2 (6)	C23—C24—C29—C28	−179.8 (6)
C4—C5—C6—C7	−1.4 (9)	C24—C25—C26—C27	2.1 (10)
C4—C5—C6—I20	177.3 (4)	C24—C25—C26—I40	−173.4 (4)
C5—C4—C9—O1	−178.9 (5)	C25—C24—C29—O21	177.1 (5)
C5—C4—C9—C8	1.0 (10)	C25—C24—C29—C28	−1.5 (10)
C5—C6—C7—C8	0.6 (11)	C25—C26—C27—C28	−2.5 (11)
C6—C7—C8—C9	0.9 (11)	C26—C27—C28—C29	0.7 (10)
C7—C8—C9—O1	178.2 (6)	C27—C28—C29—O21	−177.1 (6)
C7—C8—C9—C4	−1.7 (11)	C27—C28—C29—C24	1.2 (10)
C9—O1—C2—C3	−0.1 (7)	C29—O21—C22—C23	1.3 (6)
C9—O1—C2—C10	177.4 (6)	C29—O21—C22—C30	179.0 (6)
C9—C4—C5—C6	0.6 (9)	C29—C24—C25—C26	−0.2 (9)
C10—C2—C3—C4	−177.8 (6)	C30—C22—C23—C24	−179.8 (6)
C10—C2—C3—O19	1.4 (10)	C30—C22—C23—O39	−0.2 (10)
C10—C12—C13—C14	−178.6 (6)	C30—C32—C33—C34	178.2 (7)
C10—C12—C17—C16	−179.9 (6)	C30—C32—C37—C36	−178.7 (6)
O11—C10—C12—C13	0.4 (9)	O31—C30—C32—C33	7.0 (9)
O11—C10—C12—C17	179.9 (6)	O31—C30—C32—C37	−174.3 (6)
C12—C13—C14—C15	−3.2 (11)	C32—C33—C34—C35	0.0 (12)
C13—C12—C17—C16	−0.3 (10)	C33—C32—C37—C36	0.0 (10)
C13—C14—C15—C16	3.1 (11)	C33—C34—C35—C36	1.2 (11)
C13—C14—C15—Br18	−175.1 (5)	C33—C34—C35—Br38	−178.9 (6)
C14—C15—C16—C17	−1.7 (10)	C34—C35—C36—C37	−1.7 (11)
C15—C16—C17—C12	0.3 (10)	C35—C36—C37—C32	1.1 (11)
C17—C12—C13—C14	1.8 (10)	C37—C32—C33—C34	−0.6 (11)
Br18—C15—C16—C17	176.5 (5)	Br38—C35—C36—C37	178.3 (5)
O19—C3—C4—C5	−0.8 (11)	O39—C23—C24—C25	4.5 (12)
O19—C3—C4—C9	−178.6 (6)	O39—C23—C24—C29	−177.6 (6)
I20—C6—C7—C8	−178.1 (6)	I40—C26—C27—C28	173.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O11	0.76 (10)	2.05 (9)	2.680 (7)	140 (9)
C17—H17···O1	0.93	2.24	2.919 (8)	129
O39—H39···O31	0.79 (7)	1.90 (9)	2.617 (7)	151
C37—H37···O21	0.93	2.28	2.950 (8)	128
C13—H13···O39^i	0.93	2.50	3.231 (9)	135

Symmetry code: (i) x, y+1, z.