Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103013635/bm1532sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103013635/bm1532Isup2.hkl |
CCDC reference: 221079
The title compound was purchased from Sigma and recrystallized from diethyl ether.
H atoms were refined freely, with isotropic displacement parameters. The highest residual electron density in the final difference map was associated with the Br-atom position.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C7H7BrO2 | F(000) = 400 |
Mr = 203.04 | Dx = 1.868 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.3632 (5) Å | Cell parameters from 3029 reflections |
b = 5.3329 (2) Å | θ = 2.9–27.5° |
c = 8.4108 (3) Å | µ = 5.62 mm−1 |
β = 100.364 (2)° | T = 120 K |
V = 721.98 (4) Å3 | Rod, colourless |
Z = 4 | 0.40 × 0.24 × 0.18 mm |
Enraf Nonius KappaCCD area detector diffractometer | 1614 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 1430 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.8° |
ϕ and ω scans to fill Ewald sphere | h = −20→20 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | k = −6→6 |
Tmin = 0.212, Tmax = 0.431 | l = −10→10 |
5019 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.074P)2 + 0.392P] where P = (Fo2 + 2Fc2)/3 |
1614 reflections | (Δ/σ)max = 0.001 |
119 parameters | Δρmax = 1.17 e Å−3 |
0 restraints | Δρmin = −1.39 e Å−3 |
C7H7BrO2 | V = 721.98 (4) Å3 |
Mr = 203.04 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.3632 (5) Å | µ = 5.62 mm−1 |
b = 5.3329 (2) Å | T = 120 K |
c = 8.4108 (3) Å | 0.40 × 0.24 × 0.18 mm |
β = 100.364 (2)° |
Enraf Nonius KappaCCD area detector diffractometer | 1614 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | 1430 reflections with I > 2σ(I) |
Tmin = 0.212, Tmax = 0.431 | Rint = 0.067 |
5019 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.114 | All H-atom parameters refined |
S = 1.04 | Δρmax = 1.17 e Å−3 |
1614 reflections | Δρmin = −1.39 e Å−3 |
119 parameters |
Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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. |
Refinement. All non-hydrogen atoms were refined in SHELX97 with anisotropic thermal displacement parameters. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.06742 (2) | 0.23305 (6) | 0.85762 (4) | 0.02832 (18) | |
O1 | 0.40099 (14) | −0.1916 (4) | 1.1577 (3) | 0.0183 (4) | |
H1 | 0.399 (2) | −0.317 (7) | 1.224 (4) | 0.020 (9)* | |
O2 | 0.43380 (13) | 0.0820 (4) | 0.8520 (2) | 0.0173 (4) | |
H2 | 0.480 (2) | 0.118 (8) | 0.870 (5) | 0.028 (10)* | |
C1 | 0.32411 (16) | −0.1025 (5) | 1.0901 (3) | 0.0144 (5) | |
C2 | 0.32050 (16) | 0.1128 (5) | 0.9944 (3) | 0.0138 (5) | |
C3 | 0.2431 (2) | 0.2091 (6) | 0.9268 (3) | 0.0169 (6) | |
H3 | 0.2402 (19) | 0.357 (7) | 0.859 (4) | 0.019 (8)* | |
C4 | 0.17083 (17) | 0.0914 (5) | 0.9541 (3) | 0.0187 (6) | |
C5 | 0.17422 (18) | −0.1219 (6) | 1.0472 (3) | 0.0192 (6) | |
H5 | 0.125 (2) | −0.193 (6) | 1.067 (4) | 0.016 (8)* | |
C6 | 0.2515 (2) | −0.2198 (5) | 1.1170 (4) | 0.0188 (6) | |
H6 | 0.250 (2) | −0.349 (7) | 1.182 (4) | 0.022 (9)* | |
C7 | 0.3979 (2) | 0.2361 (5) | 0.9623 (3) | 0.0141 (6) | |
H7A | 0.3861 (19) | 0.394 (7) | 0.915 (4) | 0.019 (8)* | |
H7B | 0.438 (3) | 0.260 (5) | 1.059 (5) | 0.021 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0174 (3) | 0.0376 (3) | 0.0267 (2) | 0.00236 (11) | −0.00499 (16) | 0.00646 (11) |
O1 | 0.0177 (11) | 0.0177 (10) | 0.0186 (10) | 0.0039 (9) | 0.0009 (8) | 0.0078 (8) |
O2 | 0.0179 (10) | 0.0231 (11) | 0.0105 (9) | −0.0034 (8) | 0.0016 (7) | −0.0052 (7) |
C1 | 0.0194 (12) | 0.0141 (13) | 0.0090 (11) | 0.0009 (10) | 0.0011 (9) | −0.0031 (9) |
C2 | 0.0196 (12) | 0.0141 (13) | 0.0071 (11) | −0.0004 (10) | 0.0009 (9) | −0.0032 (9) |
C3 | 0.0220 (16) | 0.0166 (13) | 0.0109 (12) | 0.0012 (11) | −0.0003 (11) | −0.0012 (10) |
C4 | 0.0178 (13) | 0.0245 (14) | 0.0118 (12) | 0.0020 (11) | −0.0028 (10) | −0.0032 (10) |
C5 | 0.0185 (13) | 0.0214 (15) | 0.0180 (13) | −0.0052 (11) | 0.0042 (10) | −0.0034 (11) |
C6 | 0.0251 (17) | 0.0138 (13) | 0.0166 (14) | −0.0032 (11) | 0.0012 (12) | 0.0008 (10) |
C7 | 0.0201 (16) | 0.0126 (13) | 0.0083 (12) | 0.0005 (9) | −0.0012 (11) | −0.0014 (9) |
Br1—C4 | 1.897 (3) | C3—C4 | 1.394 (4) |
O1—C1 | 1.369 (3) | C3—H3 | 0.97 (4) |
O1—H1 | 0.87 (4) | C4—C5 | 1.377 (4) |
O2—C7 | 1.441 (3) | C5—C6 | 1.397 (5) |
O2—H2 | 0.76 (4) | C5—H5 | 0.93 (4) |
C1—C6 | 1.396 (4) | C6—H6 | 0.88 (4) |
C1—C2 | 1.397 (4) | C7—H7A | 0.94 (4) |
C2—C3 | 1.390 (4) | C7—H7B | 0.96 (5) |
C2—C7 | 1.494 (4) | ||
C1—O1—H1 | 113 (2) | C3—C4—Br1 | 117.9 (2) |
C7—O2—H2 | 103 (3) | C4—C5—C6 | 119.3 (3) |
O1—C1—C6 | 121.5 (3) | C4—C5—H5 | 120 (2) |
O1—C1—C2 | 117.7 (2) | C6—C5—H5 | 121 (2) |
C6—C1—C2 | 120.8 (3) | C1—C6—C5 | 119.8 (3) |
C3—C2—C1 | 118.7 (2) | C1—C6—H6 | 125 (2) |
C3—C2—C7 | 120.2 (2) | C5—C6—H6 | 115 (2) |
C1—C2—C7 | 121.1 (2) | O2—C7—C2 | 108.8 (2) |
C2—C3—C4 | 120.2 (3) | O2—C7—H7A | 108 (2) |
C2—C3—H3 | 119.0 (18) | C2—C7—H7A | 111 (2) |
C4—C3—H3 | 120.7 (18) | O2—C7—H7B | 109 (2) |
C5—C4—C3 | 121.2 (3) | C2—C7—H7B | 112 (2) |
C5—C4—Br1 | 120.9 (2) | H7A—C7—H7B | 107 (3) |
O1—C1—C2—C3 | −178.9 (2) | C3—C4—C5—C6 | 0.8 (4) |
C6—C1—C2—C3 | 0.3 (4) | Br1—C4—C5—C6 | −179.7 (2) |
O1—C1—C2—C7 | 2.1 (3) | O1—C1—C6—C5 | 179.4 (3) |
C6—C1—C2—C7 | −178.7 (2) | C2—C1—C6—C5 | 0.2 (4) |
C1—C2—C3—C4 | −0.2 (4) | C4—C5—C6—C1 | −0.8 (4) |
C7—C2—C3—C4 | 178.8 (2) | C3—C2—C7—O2 | −106.5 (3) |
C2—C3—C4—C5 | −0.3 (4) | C1—C2—C7—O2 | 72.5 (3) |
C2—C3—C4—Br1 | −179.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.88 (4) | 1.81 (4) | 2.642 (3) | 159 (3) |
O2—H2···O1ii | 0.77 (3) | 2.04 (3) | 2.781 (3) | 162 (4) |
C3—H3···Cgiii | 0.97 (3) | 2.97 (3) | 3.768 (3) | 141 (3) |
C6—H6···Cgiv | 0.88 (4) | 2.97 (3) | 3.717 (3) | 144 (3) |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y, −z+2; (iii) x, −y−1/2, z−3/2; (iv) x, −y−3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C7H7BrO2 |
Mr | 203.04 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 16.3632 (5), 5.3329 (2), 8.4108 (3) |
β (°) | 100.364 (2) |
V (Å3) | 721.98 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.62 |
Crystal size (mm) | 0.40 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995, 1997) |
Tmin, Tmax | 0.212, 0.431 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5019, 1614, 1430 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.114, 1.04 |
No. of reflections | 1614 |
No. of parameters | 119 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 1.17, −1.39 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Br1—C4 | 1.897 (3) | O2—C7 | 1.441 (3) |
O1—C1 | 1.369 (3) | C2—C7 | 1.494 (4) |
C3—C2—C7—O2 | −106.5 (3) | C1—C2—C7—O2 | 72.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | .88 (4) | 1.81 (4) | 2.642 (3) | 159 (3) |
O2—H2···O1ii | .77 (3) | 2.04 (3) | 2.781 (3) | 162 (4) |
C3—H3···Cgiii | .97 (3) | 2.97 (3) | 3.768 (3) | 141 (3) |
C6—H6···Cgiv | .88 (4) | 2.97 (3) | 3.717 (3) | 144 (3) |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y, −z+2; (iii) x, −y−1/2, z−3/2; (iv) x, −y−3/2, z−1/2. |
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Many bromophenols have been detected in blood (Olsen et al., 2002) and several antibacterial bromophenols are found in marine algae (Flodin & Whitfield, 1999). 4-Bromo-2-hydroxymethyl-phenol (also known as 5-bromo-2-hydroxybenzyl alcohol or bromosaligenin) is an anti-inflammatory agent (Merck, 1989) and spasmolytic (Negwer, 2000). When two OH groups are present in a molecule, a variety of hydrogen-bonding patterns are possible (Brock, 2002), so the main interest in the solid-state structure of the title compound, (I), is the determination of the hydrogen-bonding motifs.
A view of the molecule is shown in Fig. 1. The out-of-plane O2 atom is 1.330 (3) Å from the mean plane of the remaining non-H atoms in the molecule, as indicated by the C1—C2—C7—O2 torsion angle [72.5 (3)°]. There is no intramolecular hydrogen bonding between the two O atoms.
The intermolecular hydrogen-bonding geometry is shown in Table 2. In both cases, the intermolecular O···O separations [2.642 (3) and 2.781 (3) Å] are shorter than the corresponding intramolecular separation [3.086 (3) Å]. The hydrogen bonding is maximized by both O atoms acting as hydrogen-bond donors and acceptors, which results in an unusual three-dimensional pattern of hydrogen bonds. Fig. 2 shows a continuous corkscrew or helical arrangement of hydrogen bonds along the b axis. Each helix involves all four symmetry-related molecules in the unit cell. The formation of the helices depends on the intermolecular symmetries [(x,-y − 0.5,z + 0.5) and (1 − x,-y,2 − z)] of the hydrogen bonds, and both left-handed (L) and right-handed (R) helices are present in the lattice. The pitch of the helix equates to the length of the b axis [5.3329 (2) Å], and overall each molecule is linked to three other molecules by four classical hydrogen bonds. Fig. 3 shows that the hydrogen bonding also produces a R22(12) ring between two molecules. This dimer formation, also shown in Fig. 2, is across an inversion centre. In addition, there are weak intermolecular C—H···π interactions (Desiraju & Steiner, 1999), as shown in Fig. 4 and Table 2 where Cg is the centre of gravity of the aryl ring. No evidence of any aromatic π···π interactions is present. The shortest Br···Br intermolecular separation is 3.7173 (1) Å, which is comparable to the sum of the van der Waals radii (3.70 Å; Bondi, 1964). The crystal structure of the related saligenin (C7H8O2) molecule is also known (Zorkii et al., 1985), but no atom coordinates are available.