Two forms of (naphthalen-1-yl)boronic acid

Two polymorphs of the title compound, C₁₀H₉BO₂, were prepared by recystallization from different solvents at room temperature. Both forms demonstrate nearly identical mol­ecular structures with all naphthalene group atoms located in one plane and all boronic acid atoms in another. In each extended structure, mol­ecules form dimers, connected via two O—H...O hydrogen bonds. The dimers are connected by further O—H...O hydrogen bonds, forming layered networks. The resulting layers are practically identical in both forms but are shifted along the [010] axis in the two forms, resulting in a slightly more effective packing for the monoclinic structure compared to the ortho­rhom­bic form.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.094
• Data-to-parameter ratio = 14.9

Structure: 2

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    --  C14     ..        5.3 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    --  C17     ..        7.0 s.u.

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

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

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




Datablock: 2


Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.66 mm
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           6 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
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b). Molecular graphics: OLEX2 (Dolomanov et al., 2009) and CrystalExplorer (Spackman & Jayatilaka, 2009) for (1); OLEX2 (Dolomanov et al., 2009) for (2). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009) for (1); OLEX2 (Dolomanov et al., 2009) for (2).

(1) (Naphthalen-1-yl)boronic acid

Crystal data

C10H9BO2	Dx = 1.301 Mg m^−3
Mr = 171.98	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21	Cell parameters from 9127 reflections
a = 9.6655 (4) Å	θ = 3.0–78.2°
b = 6.2286 (3) Å	µ = 0.71 mm^−1
c = 29.1778 (13) Å	T = 173 K
V = 1756.58 (14) Å^3	Plate, colourless
Z = 8	0.59 × 0.44 × 0.14 mm
F(000) = 720

Data collection

Bruker PHOTON-100 CMOS diffractometer	3447 reflections with I > 2σ(I)
Radiation source: sealedtube	Rint = 0.040
φ and ω scans	θmax = 78.7°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −12→12
Tmin = 0.671, Tmax = 0.972	k = −7→7
52115 measured reflections	l = −36→36
3764 independent 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)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.2507P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.22 e Å^−3
3764 reflections	Δρmin = −0.15 e Å^−3
253 parameters	Absolute structure: Flack x determined using 1548 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.07 (6)

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
O3	0.24283 (16)	0.3150 (3)	0.47433 (6)	0.0415 (4)
H3	0.158 (4)	0.244 (6)	0.4672 (11)	0.062*
O4	0.48065 (16)	0.3548 (3)	0.46451 (6)	0.0398 (4)
H4	0.467 (4)	0.466 (6)	0.4831 (12)	0.060*
C11	0.3612 (2)	0.0750 (4)	0.41412 (9)	0.0367 (5)
C12	0.2783 (3)	−0.1033 (4)	0.42012 (11)	0.0472 (6)
H12	0.222 (2)	−0.1146 (6)	0.4475 (10)	0.057*
C13	0.2731 (3)	−0.2707 (5)	0.38704 (13)	0.0581 (8)
H13	0.220 (2)	−0.383 (5)	0.3918 (2)	0.070*
C14	0.3497 (3)	−0.2587 (5)	0.34829 (12)	0.0549 (8)
H14	0.3444 (4)	−0.387 (4)	0.3237 (8)	0.066*
C15	0.4357 (3)	−0.0818 (4)	0.33976 (10)	0.0451 (6)
C16	0.5152 (3)	−0.0637 (6)	0.29893 (10)	0.0566 (8)
H16	0.5105 (4)	−0.182 (4)	0.2757 (9)	0.068*
C17	0.5970 (3)	0.1086 (6)	0.29054 (10)	0.0555 (8)
H17	0.653 (2)	0.1169 (6)	0.2611 (11)	0.067*
C18	0.6038 (3)	0.2752 (5)	0.32268 (9)	0.0485 (7)
H18	0.666 (2)	0.407 (5)	0.3163 (2)	0.058*
C19	0.5287 (2)	0.2649 (4)	0.36254 (8)	0.0389 (5)
H19	0.5350	0.3799	0.3838	0.047*
C20	0.4422 (2)	0.0882 (4)	0.37291 (8)	0.0358 (5)
B2	0.3611 (3)	0.2548 (5)	0.45182 (10)	0.0352 (6)
O1	0.44946 (17)	0.6845 (3)	0.52575 (6)	0.0410 (4)
H1	0.520 (4)	0.747 (6)	0.5329 (13)	0.061*
O2	0.21178 (16)	0.6447 (3)	0.53618 (6)	0.0393 (4)
H2	0.224 (4)	0.548 (5)	0.5138 (12)	0.059*
C1	0.3326 (2)	0.9282 (4)	0.58539 (8)	0.0337 (5)
C2	0.4169 (2)	1.1032 (4)	0.57782 (10)	0.0417 (6)
H2A	0.4712	1.1076	0.5507	0.050*
C3	0.4253 (3)	1.2758 (4)	0.60894 (11)	0.0484 (7)
H3A	0.4842	1.3941	0.6025	0.058*
C4	0.3491 (3)	1.2734 (4)	0.64824 (11)	0.0460 (6)
H4A	0.3552	1.3901	0.6691	0.055*
C5	0.2613 (2)	1.0981 (4)	0.65810 (9)	0.0386 (5)
C6	0.1826 (3)	1.0920 (5)	0.69941 (9)	0.0462 (6)
H6	0.1876	1.2092	0.7202	0.055*
C7	0.1010 (3)	0.9220 (5)	0.70950 (9)	0.0482 (6)
H7	0.0499	0.9201	0.7373	0.058*
C8	0.0916 (3)	0.7484 (5)	0.67893 (9)	0.0437 (6)
H8	0.0343	0.6294	0.6862	0.052*
C9	0.1647 (2)	0.7492 (4)	0.63858 (8)	0.0361 (5)
H9	0.1567	0.6308	0.6182	0.043*
C10	0.2520 (2)	0.9235 (4)	0.62674 (8)	0.0328 (5)
B1	0.3317 (3)	0.7451 (5)	0.54832 (9)	0.0347 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0220 (7)	0.0608 (11)	0.0418 (9)	−0.0033 (8)	0.0009 (6)	−0.0085 (8)
O4	0.0227 (7)	0.0537 (10)	0.0430 (10)	−0.0004 (8)	−0.0010 (6)	−0.0104 (8)
C11	0.0239 (10)	0.0383 (12)	0.0479 (13)	0.0028 (9)	−0.0073 (9)	−0.0001 (11)
C12	0.0329 (11)	0.0453 (14)	0.0633 (17)	−0.0010 (11)	−0.0080 (12)	0.0086 (12)
C13	0.0457 (15)	0.0360 (13)	0.093 (3)	−0.0063 (12)	−0.0258 (16)	0.0035 (14)
C14	0.0487 (16)	0.0426 (14)	0.073 (2)	0.0077 (12)	−0.0200 (14)	−0.0160 (14)
C15	0.0370 (12)	0.0442 (14)	0.0541 (16)	0.0115 (10)	−0.0158 (11)	−0.0128 (12)
C16	0.0511 (16)	0.0719 (19)	0.0469 (16)	0.0244 (15)	−0.0136 (12)	−0.0248 (15)
C17	0.0450 (15)	0.079 (2)	0.0421 (15)	0.0145 (15)	−0.0012 (11)	−0.0093 (14)
C18	0.0381 (14)	0.0660 (18)	0.0414 (14)	0.0042 (13)	−0.0002 (10)	−0.0029 (12)
C19	0.0309 (12)	0.0461 (13)	0.0396 (12)	0.0038 (10)	−0.0037 (10)	−0.0061 (10)
C20	0.0270 (9)	0.0387 (12)	0.0417 (13)	0.0079 (9)	−0.0074 (9)	−0.0064 (10)
B2	0.0231 (12)	0.0454 (14)	0.0371 (13)	0.0006 (11)	−0.0011 (10)	0.0038 (11)
O1	0.0234 (7)	0.0568 (11)	0.0427 (10)	−0.0046 (8)	0.0025 (6)	−0.0069 (8)
O2	0.0212 (7)	0.0542 (10)	0.0424 (9)	0.0002 (7)	0.0011 (6)	−0.0093 (8)
C1	0.0242 (9)	0.0371 (11)	0.0399 (12)	0.0030 (9)	−0.0045 (8)	0.0034 (10)
C2	0.0284 (11)	0.0433 (13)	0.0533 (15)	−0.0009 (10)	−0.0037 (10)	0.0086 (11)
C3	0.0369 (14)	0.0342 (12)	0.0741 (19)	−0.0046 (11)	−0.0109 (13)	0.0058 (12)
C4	0.0382 (14)	0.0351 (12)	0.0647 (18)	0.0031 (11)	−0.0148 (11)	−0.0056 (12)
C5	0.0313 (11)	0.0391 (12)	0.0453 (14)	0.0080 (10)	−0.0107 (9)	−0.0030 (10)
C6	0.0454 (14)	0.0501 (14)	0.0430 (14)	0.0113 (12)	−0.0084 (11)	−0.0114 (11)
C7	0.0440 (14)	0.0630 (16)	0.0377 (13)	0.0078 (13)	0.0009 (10)	−0.0025 (12)
C8	0.0379 (13)	0.0500 (14)	0.0433 (13)	0.0023 (12)	0.0010 (10)	0.0045 (10)
C9	0.0303 (11)	0.0386 (11)	0.0395 (12)	0.0016 (9)	−0.0025 (9)	−0.0011 (9)
C10	0.0248 (9)	0.0345 (11)	0.0392 (12)	0.0050 (9)	−0.0070 (8)	0.0009 (9)
B1	0.0228 (12)	0.0439 (13)	0.0374 (13)	0.0014 (10)	−0.0004 (9)	0.0007 (11)

Geometric parameters (Å, º)

O3—H3	0.95 (4)	O1—H1	0.81 (4)
O3—B2	1.371 (3)	O1—B1	1.368 (3)
O4—H4	0.89 (4)	O2—H2	0.90 (3)
O4—B2	1.363 (3)	O2—B1	1.364 (3)
C11—C12	1.381 (4)	C1—C2	1.379 (4)
C11—C20	1.438 (3)	C1—C10	1.436 (3)
C11—B2	1.570 (4)	C1—B1	1.572 (4)
C12—H12	0.97 (3)	C2—H2A	0.9500
C12—C13	1.422 (5)	C2—C3	1.410 (4)
C13—H13	0.88 (4)	C3—H3A	0.9500
C13—C14	1.353 (5)	C3—C4	1.363 (4)
C14—H14	1.07 (4)	C4—H4A	0.9500
C14—C15	1.403 (4)	C4—C5	1.413 (4)
C15—C16	1.422 (4)	C5—C6	1.426 (4)
C15—C20	1.435 (3)	C5—C10	1.424 (3)
C16—H16	1.00 (4)	C6—H6	0.9500
C16—C17	1.355 (5)	C6—C7	1.353 (4)
C17—H17	1.02 (4)	C7—H7	0.9500
C17—C18	1.400 (4)	C7—C8	1.405 (4)
C18—H18	1.03 (4)	C8—H8	0.9500
C18—C19	1.373 (3)	C8—C9	1.373 (4)
C19—H19	0.9500	C9—H9	0.9500
C19—C20	1.415 (3)	C9—C10	1.417 (3)
B2—O3—H3	119 (2)	B1—O1—H1	116 (3)
B2—O4—H4	113 (2)	B1—O2—H2	113 (2)
C12—C11—C20	117.9 (2)	C2—C1—C10	118.1 (2)
C12—C11—B2	119.0 (2)	C2—C1—B1	117.8 (2)
C20—C11—B2	123.1 (2)	C10—C1—B1	124.1 (2)
C11—C12—H12	119.2	C1—C2—H2A	118.9
C11—C12—C13	121.6 (3)	C1—C2—C3	122.3 (3)
C13—C12—H12	119.2	C3—C2—H2A	118.9
C12—C13—H13	119.7	C2—C3—H3A	119.9
C14—C13—C12	120.5 (3)	C4—C3—C2	120.1 (2)
C14—C13—H13	119.7	C4—C3—H3A	119.9
C13—C14—H14	119.5	C3—C4—H4A	119.9
C13—C14—C15	121.0 (3)	C3—C4—C5	120.3 (3)
C15—C14—H14	119.5	C5—C4—H4A	119.9
C14—C15—C16	122.1 (3)	C4—C5—C6	120.9 (2)
C14—C15—C20	119.1 (3)	C4—C5—C10	119.8 (2)
C16—C15—C20	118.8 (3)	C10—C5—C6	119.3 (2)
C15—C16—H16	119.0	C5—C6—H6	119.5
C17—C16—C15	122.0 (3)	C7—C6—C5	121.1 (2)
C17—C16—H16	119.0	C7—C6—H6	119.5
C16—C17—H17	120.2	C6—C7—H7	119.9
C16—C17—C18	119.6 (3)	C6—C7—C8	120.1 (3)
C18—C17—H17	120.2	C8—C7—H7	119.9
C17—C18—H18	119.7	C7—C8—H8	119.7
C19—C18—C17	120.5 (3)	C9—C8—C7	120.6 (3)
C19—C18—H18	119.7	C9—C8—H8	119.7
C18—C19—H19	119.0	C8—C9—H9	119.4
C18—C19—C20	122.0 (2)	C8—C9—C10	121.2 (2)
C20—C19—H19	119.0	C10—C9—H9	119.4
C15—C20—C11	119.8 (2)	C5—C10—C1	119.3 (2)
C19—C20—C11	123.0 (2)	C9—C10—C1	122.9 (2)
C19—C20—C15	117.1 (2)	C9—C10—C5	117.8 (2)
O3—B2—C11	122.1 (2)	O1—B1—C1	121.8 (2)
O4—B2—O3	116.9 (2)	O2—B1—O1	117.1 (2)
O4—B2—C11	121.1 (2)	O2—B1—C1	121.0 (2)
C11—C12—C13—C14	−0.4 (4)	C1—C2—C3—C4	0.3 (4)
C12—C11—C20—C15	−0.3 (3)	C2—C1—C10—C5	0.2 (3)
C12—C11—C20—C19	178.6 (2)	C2—C1—C10—C9	−178.3 (2)
C12—C11—B2—O3	−38.2 (3)	C2—C1—B1—O1	37.5 (3)
C12—C11—B2—O4	140.1 (2)	C2—C1—B1—O2	−140.3 (2)
C12—C13—C14—C15	0.0 (4)	C2—C3—C4—C5	0.0 (4)
C13—C14—C15—C16	−178.8 (3)	C3—C4—C5—C6	179.0 (2)
C13—C14—C15—C20	0.2 (4)	C3—C4—C5—C10	−0.2 (3)
C14—C15—C16—C17	179.2 (3)	C4—C5—C6—C7	−178.4 (2)
C14—C15—C20—C11	0.0 (3)	C4—C5—C10—C1	0.1 (3)
C14—C15—C20—C19	−179.1 (2)	C4—C5—C10—C9	178.7 (2)
C15—C16—C17—C18	−0.3 (4)	C5—C6—C7—C8	−0.5 (4)
C16—C15—C20—C11	179.0 (2)	C6—C5—C10—C1	−179.2 (2)
C16—C15—C20—C19	0.0 (3)	C6—C5—C10—C9	−0.6 (3)
C16—C17—C18—C19	0.2 (4)	C6—C7—C8—C9	−0.1 (4)
C17—C18—C19—C20	0.0 (4)	C7—C8—C9—C10	0.4 (4)
C18—C19—C20—C11	−179.1 (2)	C8—C9—C10—C1	178.5 (2)
C18—C19—C20—C15	−0.1 (3)	C8—C9—C10—C5	0.0 (3)
C20—C11—C12—C13	0.5 (3)	C10—C1—C2—C3	−0.4 (3)
C20—C11—B2—O3	140.8 (2)	C10—C1—B1—O1	−142.0 (2)
C20—C11—B2—O4	−41.0 (3)	C10—C1—B1—O2	40.3 (3)
C20—C15—C16—C17	0.2 (4)	C10—C5—C6—C7	0.9 (3)
B2—C11—C12—C13	179.6 (2)	B1—C1—C2—C3	−179.9 (2)
B2—C11—C20—C15	−179.3 (2)	B1—C1—C10—C5	179.7 (2)
B2—C11—C20—C19	−0.3 (3)	B1—C1—C10—C9	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.81 (4)	1.98 (4)	2.766 (2)	165 (4)
O2—H2···O3	0.90 (3)	1.86 (3)	2.750 (3)	171 (3)
O3—H3···O4^ii	0.96 (4)	1.82 (4)	2.761 (2)	167 (3)
O4—H4···O1	0.89 (4)	1.85 (4)	2.739 (3)	175 (3)
C9—H9···O2	0.95	2.45	3.092 (3)	124
C19—H19···O4	0.95	2.42	3.063 (3)	125

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

(2) (Naphthalen-1-yl)boronic acid

Crystal data

C10H9BO2	F(000) = 360
Mr = 171.98	Dx = 1.306 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.8469 (11) Å	Cell parameters from 9898 reflections
b = 6.1023 (4) Å	θ = 3.0–77.0°
c = 9.6797 (7) Å	µ = 0.71 mm^−1
β = 93.978 (3)°	T = 173 K
V = 874.87 (11) Å^3	Prism, colourless
Z = 4	0.66 × 0.18 × 0.16 mm

Data collection

Bruker PHOTON-100 CMOS diffractometer	1576 reflections with I > 2σ(I)
Radiation source: sealedtube	Rint = 0.038
φ and ω scans	θmax = 77.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −18→18
Tmin = 0.759, Tmax = 0.951	k = −7→7
25253 measured reflections	l = −12→11
1857 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.2015P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1857 reflections	Δρmax = 0.23 e Å^−3
133 parameters	Δρmin = −0.15 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	0.42757 (6)	0.14734 (15)	0.62491 (7)	0.0348 (2)
H1	0.4697 (12)	0.043 (3)	0.6194 (17)	0.058 (5)*
O2	0.44930 (6)	0.18505 (15)	0.39004 (8)	0.0361 (2)
H2	0.4335 (12)	0.247 (3)	0.309 (2)	0.067 (5)*
C1	0.32826 (8)	0.42799 (19)	0.49000 (11)	0.0301 (3)
C2	0.34171 (9)	0.6083 (2)	0.40723 (12)	0.0374 (3)
H2A	0.3975 (9)	0.6190 (3)	0.3608 (7)	0.045*
C3	0.27729 (10)	0.7770 (2)	0.38806 (13)	0.0441 (3)
H3	0.2893 (2)	0.903 (2)	0.3287 (10)	0.053*
C4	0.19841 (10)	0.7660 (2)	0.45170 (13)	0.0431 (3)
H4	0.1527 (8)	0.887 (2)	0.4375 (3)	0.052*
C5	0.18023 (8)	0.5861 (2)	0.53761 (12)	0.0356 (3)
C6	0.09731 (9)	0.5709 (2)	0.60194 (14)	0.0445 (3)
H6	0.0525 (8)	0.688 (2)	0.5877 (3)	0.053*
C7	0.07934 (9)	0.3962 (3)	0.68300 (14)	0.0477 (3)
H7	0.0219 (10)	0.3879 (3)	0.7264 (8)	0.057*
C8	0.14332 (9)	0.2281 (2)	0.70431 (13)	0.0411 (3)
H8	0.1299 (2)	0.100 (2)	0.7651 (10)	0.049*
C9	0.22382 (8)	0.2367 (2)	0.64330 (11)	0.0327 (3)
H9	0.2672 (6)	0.1175 (18)	0.6589 (3)	0.039*
C10	0.24527 (8)	0.41549 (18)	0.55791 (11)	0.0296 (3)
B1	0.40328 (9)	0.2462 (2)	0.50178 (12)	0.0300 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0376 (5)	0.0461 (5)	0.0209 (4)	0.0093 (4)	0.0038 (3)	0.0008 (3)
O2	0.0375 (5)	0.0500 (5)	0.0212 (4)	0.0078 (4)	0.0055 (3)	0.0041 (4)
C1	0.0372 (6)	0.0315 (6)	0.0212 (5)	−0.0021 (5)	−0.0008 (4)	−0.0028 (4)
C2	0.0476 (7)	0.0370 (6)	0.0274 (6)	−0.0065 (5)	0.0009 (5)	0.0002 (5)
C3	0.0669 (9)	0.0306 (6)	0.0333 (6)	−0.0033 (6)	−0.0060 (6)	0.0046 (5)
C4	0.0575 (8)	0.0333 (6)	0.0367 (7)	0.0098 (6)	−0.0093 (6)	−0.0037 (5)
C5	0.0429 (7)	0.0357 (6)	0.0271 (6)	0.0062 (5)	−0.0058 (5)	−0.0069 (5)
C6	0.0384 (7)	0.0532 (8)	0.0413 (7)	0.0139 (6)	−0.0034 (5)	−0.0098 (6)
C7	0.0334 (7)	0.0664 (9)	0.0434 (7)	0.0036 (6)	0.0047 (5)	−0.0042 (7)
C8	0.0368 (6)	0.0500 (7)	0.0366 (7)	−0.0038 (6)	0.0036 (5)	0.0016 (6)
C9	0.0335 (6)	0.0348 (6)	0.0293 (6)	0.0010 (5)	−0.0007 (4)	−0.0010 (5)
C10	0.0349 (6)	0.0311 (6)	0.0221 (5)	0.0009 (5)	−0.0022 (4)	−0.0051 (4)
B1	0.0308 (6)	0.0366 (7)	0.0226 (6)	−0.0031 (5)	0.0024 (4)	−0.0013 (5)

Geometric parameters (Å, º)

O1—H1	0.899 (19)	C4—C5	1.4146 (18)
O1—B1	1.3620 (15)	C5—C6	1.4206 (19)
O2—H2	0.886 (19)	C5—C10	1.4243 (16)
O2—B1	1.3706 (14)	C6—H6	0.979 (16)
C1—C2	1.3839 (16)	C6—C7	1.361 (2)
C1—C10	1.4382 (16)	C7—H7	0.977 (16)
C1—B1	1.5705 (18)	C7—C8	1.4036 (19)
C2—H2A	0.971 (15)	C8—H8	1.008 (16)
C2—C3	1.4085 (19)	C8—C9	1.3703 (17)
C3—H3	0.983 (16)	C9—H9	0.977 (14)
C3—C4	1.362 (2)	C9—C10	1.4180 (16)
C4—H4	1.004 (16)
B1—O1—H1	114.0 (10)	C7—C6—C5	120.98 (12)
B1—O2—H2	117.8 (11)	C7—C6—H6	119.5
C2—C1—C10	118.00 (11)	C6—C7—H7	120.0
C2—C1—B1	118.27 (11)	C6—C7—C8	119.95 (12)
C10—C1—B1	123.72 (10)	C8—C7—H7	120.0
C1—C2—H2A	118.9	C7—C8—H8	119.7
C1—C2—C3	122.23 (12)	C9—C8—C7	120.68 (13)
C3—C2—H2A	118.9	C9—C8—H8	119.7
C2—C3—H3	119.9	C8—C9—H9	119.4
C4—C3—C2	120.12 (12)	C8—C9—C10	121.23 (11)
C4—C3—H3	119.9	C10—C9—H9	119.4
C3—C4—H4	119.7	C5—C10—C1	119.49 (11)
C3—C4—C5	120.60 (12)	C9—C10—C1	122.78 (10)
C5—C4—H4	119.7	C9—C10—C5	117.72 (11)
C4—C5—C6	121.00 (12)	O1—B1—O2	116.98 (11)
C4—C5—C10	119.56 (12)	O1—B1—C1	121.32 (10)
C6—C5—C10	119.43 (12)	O2—B1—C1	121.66 (10)
C5—C6—H6	119.5
C1—C2—C3—C4	−0.16 (19)	C6—C5—C10—C9	−0.34 (16)
C2—C1—C10—C5	0.31 (15)	C6—C7—C8—C9	−0.5 (2)
C2—C1—C10—C9	179.01 (10)	C7—C8—C9—C10	0.45 (18)
C2—C1—B1—O1	139.56 (12)	C8—C9—C10—C1	−178.73 (11)
C2—C1—B1—O2	−38.24 (16)	C8—C9—C10—C5	−0.01 (16)
C2—C3—C4—C5	0.06 (19)	C10—C1—C2—C3	−0.04 (17)
C3—C4—C5—C6	−178.59 (12)	C10—C1—B1—O1	−41.91 (16)
C3—C4—C5—C10	0.22 (18)	C10—C1—B1—O2	140.30 (11)
C4—C5—C6—C7	179.08 (12)	C10—C5—C6—C7	0.27 (18)
C4—C5—C10—C1	−0.41 (16)	B1—C1—C2—C3	178.58 (11)
C4—C5—C10—C9	−179.17 (10)	B1—C1—C10—C5	−178.22 (10)
C5—C6—C7—C8	0.2 (2)	B1—C1—C10—C9	0.47 (16)
C6—C5—C10—C1	178.42 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.897 (18)	1.846 (18)	2.7411 (13)	176.3 (17)
O2—H2···O1^ii	0.888 (19)	1.891 (19)	2.7607 (11)	166.0 (17)
C9—H9···O1	0.98 (1)	2.43 (1)	3.0911 (15)	124 (1)

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