Crystal structure of (2′,3,6′-tri­chloro­biphenyl-2-yl)boronic acid tetra­hydro­furan monosolvate

In this manuscript the mol­ecular and supra­molecular structure of 2′,3,6′-tri­chloro­biphenyl-2-ylboronic acid tetra­hydro­furan monosolvate is presented

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.085
• Data-to-parameter ratio = 28.5

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00300 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl2    ..  Cl3     ..       3.39 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        250 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

(2',3,6'-Trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate

Crystal data

C12H8BCl3O2·C4H8O	F(000) = 384
Mr = 373.45	Dx = 1.429 Mg m^−3
Triclinic, P1	Melting point: 411 K
a = 8.3306 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7122 (2) Å	Cell parameters from 14113 reflections
c = 12.4307 (4) Å	θ = 2.4–32.4°
α = 98.683 (3)°	µ = 0.54 mm^−1
β = 97.737 (3)°	T = 130 K
γ = 99.398 (3)°	Fragment, colourless
V = 868.07 (5) Å^3	0.15 × 0.12 × 0.10 mm
Z = 2

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	6107 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5162 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 5.2195 pixels mm^-1	θmax = 32.6°, θmin = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −13→13
Tmin = 0.795, Tmax = 1.000	l = −18→18
28647 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0328P)^2 + 0.3549P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6107 reflections	Δρmax = 0.45 e Å^−3
214 parameters	Δρmin = −0.36 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro (Agilent Technologies, 2014), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

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

	x	y	z	Uiso*/Ueq
C1	0.77416 (13)	0.33187 (12)	0.22248 (8)	0.01544 (18)
C2	0.85513 (13)	0.33777 (12)	0.13113 (9)	0.01761 (19)
C3	0.77605 (15)	0.28436 (14)	0.02290 (9)	0.0221 (2)
H3	0.8355	0.2914	−0.0368	0.027*
C5	0.52304 (15)	0.21255 (15)	0.09167 (10)	0.0233 (2)
H5	0.4085	0.1690	0.0782	0.028*
C6	0.60414 (13)	0.26808 (13)	0.19972 (9)	0.01703 (19)
C7	0.50529 (13)	0.26201 (13)	0.29144 (9)	0.01742 (19)
C8	0.47656 (14)	0.12861 (13)	0.34104 (9)	0.0188 (2)
C9	0.38144 (14)	0.12012 (15)	0.42447 (10)	0.0230 (2)
H9	0.3646	0.0276	0.4565	0.028*
C10	0.31167 (15)	0.24852 (16)	0.46023 (11)	0.0263 (2)
H10	0.2466	0.2441	0.5172	0.032*
C11	0.43238 (14)	0.38827 (13)	0.33025 (10)	0.0211 (2)
C12	0.33610 (15)	0.38351 (16)	0.41341 (11)	0.0262 (2)
H12	0.2879	0.4714	0.4377	0.031*
C13	0.60897 (16)	0.22065 (15)	0.00366 (10)	0.0257 (2)
H13	0.5531	0.1825	−0.0697	0.031*
C14	0.82695 (16)	0.75012 (14)	0.14313 (10)	0.0241 (2)
H14A	0.7067	0.7154	0.1184	0.029*
H14B	0.8843	0.6702	0.1077	0.029*
C15	0.88574 (17)	0.91105 (15)	0.11452 (11)	0.0283 (3)
H15A	0.8014	0.9785	0.1202	0.034*
H15B	0.9142	0.9012	0.0393	0.034*
C16	1.03885 (18)	0.97668 (16)	0.20241 (12)	0.0325 (3)
H16A	1.1369	0.9378	0.1804	0.039*
H16B	1.0621	1.0937	0.2165	0.039*
C17	0.9899 (2)	0.91251 (17)	0.30259 (12)	0.0358 (3)
H17A	1.0868	0.8873	0.3471	0.043*
H17B	0.9443	0.9914	0.3495	0.043*
B1	0.86796 (14)	0.39672 (14)	0.34516 (10)	0.0160 (2)
O1	0.92407 (11)	0.55444 (9)	0.38238 (7)	0.02050 (16)
O2	0.89019 (11)	0.29285 (10)	0.41379 (7)	0.02293 (17)
O3	0.86646 (12)	0.77103 (10)	0.26144 (7)	0.02631 (19)
Cl1	0.56394 (4)	−0.03377 (3)	0.29838 (2)	0.02648 (7)
Cl2	0.46307 (4)	0.55927 (3)	0.27352 (3)	0.02936 (8)
Cl3	1.06696 (3)	0.41387 (4)	0.15296 (2)	0.02402 (7)
H1A	0.902 (2)	0.6121 (19)	0.3383 (13)	0.036*
H2A	0.941 (2)	0.336 (2)	0.4767 (12)	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0179 (5)	0.0142 (4)	0.0137 (4)	0.0028 (3)	0.0005 (3)	0.0028 (3)
C2	0.0196 (5)	0.0163 (4)	0.0168 (5)	0.0029 (4)	0.0027 (4)	0.0034 (4)
C3	0.0289 (6)	0.0237 (5)	0.0148 (5)	0.0061 (4)	0.0047 (4)	0.0040 (4)
C5	0.0212 (5)	0.0264 (6)	0.0181 (5)	0.0002 (4)	−0.0030 (4)	0.0013 (4)
C6	0.0186 (5)	0.0169 (4)	0.0146 (4)	0.0025 (4)	0.0002 (4)	0.0028 (4)
C7	0.0156 (4)	0.0194 (5)	0.0152 (4)	0.0009 (4)	0.0001 (3)	0.0015 (4)
C8	0.0197 (5)	0.0202 (5)	0.0150 (5)	0.0025 (4)	0.0003 (4)	0.0014 (4)
C9	0.0208 (5)	0.0284 (6)	0.0192 (5)	0.0013 (4)	0.0022 (4)	0.0065 (4)
C10	0.0186 (5)	0.0363 (7)	0.0236 (6)	0.0033 (5)	0.0060 (4)	0.0044 (5)
C11	0.0176 (5)	0.0196 (5)	0.0243 (5)	0.0016 (4)	0.0010 (4)	0.0027 (4)
C12	0.0193 (5)	0.0296 (6)	0.0293 (6)	0.0065 (4)	0.0056 (4)	0.0005 (5)
C13	0.0305 (6)	0.0290 (6)	0.0138 (5)	0.0024 (5)	−0.0024 (4)	0.0013 (4)
C14	0.0267 (6)	0.0221 (5)	0.0226 (5)	0.0031 (4)	0.0000 (4)	0.0059 (4)
C15	0.0332 (7)	0.0258 (6)	0.0278 (6)	0.0044 (5)	0.0057 (5)	0.0114 (5)
C16	0.0333 (7)	0.0243 (6)	0.0375 (7)	−0.0023 (5)	0.0049 (6)	0.0068 (5)
C17	0.0411 (8)	0.0261 (6)	0.0328 (7)	−0.0066 (5)	−0.0064 (6)	0.0072 (5)
B1	0.0152 (5)	0.0170 (5)	0.0146 (5)	0.0022 (4)	0.0009 (4)	0.0015 (4)
O1	0.0278 (4)	0.0162 (4)	0.0149 (4)	0.0019 (3)	−0.0030 (3)	0.0027 (3)
O2	0.0302 (4)	0.0179 (4)	0.0170 (4)	0.0010 (3)	−0.0053 (3)	0.0036 (3)
O3	0.0328 (5)	0.0202 (4)	0.0233 (4)	−0.0005 (3)	−0.0017 (3)	0.0072 (3)
Cl1	0.04097 (17)	0.02093 (13)	0.02001 (13)	0.00986 (11)	0.00736 (11)	0.00481 (10)
Cl2	0.02627 (15)	0.02037 (13)	0.04284 (18)	0.00462 (10)	0.00663 (12)	0.00884 (12)
Cl3	0.01988 (13)	0.02816 (14)	0.02462 (14)	0.00239 (10)	0.00640 (10)	0.00636 (11)

Geometric parameters (Å, º)

C1—C2	1.3999 (15)	C11—Cl2	1.7388 (12)
C1—C6	1.4081 (15)	C12—H12	0.9500
C1—B1	1.5907 (16)	C13—H13	0.9500
C2—C3	1.3902 (16)	C14—O3	1.4400 (15)
C2—Cl3	1.7498 (11)	C14—C15	1.5183 (17)
C3—C13	1.3859 (18)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C5—C13	1.3900 (17)	C15—C16	1.532 (2)
C5—C6	1.3954 (15)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.4959 (15)	C16—C17	1.517 (2)
C7—C11	1.3959 (16)	C16—H16A	0.9900
C7—C8	1.3976 (15)	C16—H16B	0.9900
C8—C9	1.3908 (16)	C17—O3	1.4465 (16)
C8—Cl1	1.7395 (12)	C17—H17A	0.9900
C9—C10	1.3851 (18)	C17—H17B	0.9900
C9—H9	0.9500	B1—O2	1.3514 (14)
C10—C12	1.3869 (19)	B1—O1	1.3641 (14)
C10—H10	0.9500	O1—H1A	0.821 (14)
C11—C12	1.3924 (17)	O2—H2A	0.838 (14)
C2—C1—C6	116.31 (9)	C3—C13—C5	120.03 (11)
C2—C1—B1	121.95 (9)	C3—C13—H13	120.0
C6—C1—B1	121.73 (9)	C5—C13—H13	120.0
C3—C2—C1	123.29 (10)	O3—C14—C15	105.36 (10)
C3—C2—Cl3	117.77 (9)	O3—C14—H14A	110.7
C1—C2—Cl3	118.93 (8)	C15—C14—H14A	110.7
C13—C3—C2	118.82 (11)	O3—C14—H14B	110.7
C13—C3—H3	120.6	C15—C14—H14B	110.7
C2—C3—H3	120.6	H14A—C14—H14B	108.8
C13—C5—C6	120.36 (11)	C14—C15—C16	102.13 (10)
C13—C5—H5	119.8	C14—C15—H15A	111.3
C6—C5—H5	119.8	C16—C15—H15A	111.3
C5—C6—C1	121.18 (10)	C14—C15—H15B	111.3
C5—C6—C7	118.41 (10)	C16—C15—H15B	111.3
C1—C6—C7	120.40 (9)	H15A—C15—H15B	109.2
C11—C7—C8	116.15 (10)	C17—C16—C15	102.58 (11)
C11—C7—C6	121.66 (10)	C17—C16—H16A	111.3
C8—C7—C6	122.17 (10)	C15—C16—H16A	111.3
C9—C8—C7	122.68 (11)	C17—C16—H16B	111.3
C9—C8—Cl1	118.09 (9)	C15—C16—H16B	111.3
C7—C8—Cl1	119.23 (9)	H16A—C16—H16B	109.2
C10—C9—C8	119.03 (11)	O3—C17—C16	106.63 (11)
C10—C9—H9	120.5	O3—C17—H17A	110.4
C8—C9—H9	120.5	C16—C17—H17A	110.4
C9—C10—C12	120.49 (11)	O3—C17—H17B	110.4
C9—C10—H10	119.8	C16—C17—H17B	110.4
C12—C10—H10	119.8	H17A—C17—H17B	108.6
C12—C11—C7	122.63 (11)	O2—B1—O1	119.71 (10)
C12—C11—Cl2	118.30 (9)	O2—B1—C1	118.96 (9)
C7—C11—Cl2	119.07 (9)	O1—B1—C1	121.33 (9)
C10—C12—C11	119.01 (12)	B1—O1—H1A	115.3 (13)
C10—C12—H12	120.5	B1—O2—H2A	113.1 (12)
C11—C12—H12	120.5	C14—O3—C17	109.77 (10)
C6—C1—C2—C3	−0.15 (16)	Cl1—C8—C9—C10	179.55 (9)
B1—C1—C2—C3	−178.97 (10)	C8—C9—C10—C12	0.09 (18)
C6—C1—C2—Cl3	−179.42 (8)	C8—C7—C11—C12	−0.07 (17)
B1—C1—C2—Cl3	1.76 (14)	C6—C7—C11—C12	178.17 (11)
C1—C2—C3—C13	−0.56 (17)	C8—C7—C11—Cl2	179.60 (8)
Cl3—C2—C3—C13	178.72 (9)	C6—C7—C11—Cl2	−2.15 (15)
C13—C5—C6—C1	−0.63 (18)	C9—C10—C12—C11	−0.26 (19)
C13—C5—C6—C7	177.91 (11)	C7—C11—C12—C10	0.25 (18)
C2—C1—C6—C5	0.74 (16)	Cl2—C11—C12—C10	−179.42 (10)
B1—C1—C6—C5	179.56 (10)	C2—C3—C13—C5	0.69 (18)
C2—C1—C6—C7	−177.77 (9)	C6—C5—C13—C3	−0.11 (19)
B1—C1—C6—C7	1.05 (15)	O3—C14—C15—C16	33.84 (13)
C5—C6—C7—C11	−90.69 (13)	C14—C15—C16—C17	−35.53 (14)
C1—C6—C7—C11	87.86 (13)	C15—C16—C17—O3	25.23 (15)
C5—C6—C7—C8	87.44 (14)	C2—C1—B1—O2	−111.66 (12)
C1—C6—C7—C8	−94.00 (13)	C6—C1—B1—O2	69.59 (14)
C11—C7—C8—C9	−0.11 (16)	C2—C1—B1—O1	69.17 (14)
C6—C7—C8—C9	−178.35 (10)	C6—C1—B1—O1	−109.58 (12)
C11—C7—C8—Cl1	−179.56 (8)	C15—C14—O3—C17	−18.86 (14)
C6—C7—C8—Cl1	2.21 (14)	C16—C17—O3—C14	−4.30 (16)
C7—C8—C9—C10	0.10 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.82 (1)	1.84 (1)	2.6475 (12)	169 (2)
O2—H2A···O1^i	0.84 (1)	1.96 (1)	2.7997 (12)	175 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.