5-Benzoyl-13-bromo-4-hy-droxy[2.2]paracyclo-phane.

The title compound, C(23)H(19)BrO(2), was synthesized from 13-bromo-4-hy-droxy[2.2]paracyclo-phane and benzoyl chloride. The hy-droxy and carbonyl groups are involved in intra-molecular O-H⋯O hydrogen bonding. The crystal packing exhibits weak C-H⋯O inter-actions, which link the mol-ecules into sheets parallel to the bc plane.

Related literature

For a related structure, see: Hong et al. (2011 ▶). For background to [2.2]paracyclo­phanes, see: Fache et al. (2000 ▶); Danilova et al. (2003 ▶). For details of the synthesis, see: Xin et al. (2010 ▶).

Experimental

Crystal data

C23H19BrO2

M = 407.29

Monoclinic,

a = 12.5250 (18) Å

b = 7.8885 (12) Å

c = 19.143 (3) Å

β = 106.812 (3)°

V = 1810.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.29 mm−1

T = 273 K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2007 ▶) T min = 0.804, T max = 0.838

7291 measured reflections

2586 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.033

θmax = 23.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.147

S = 1.04

2586 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013803/cv5263sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013803/cv5263Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19BrO2	F(000) = 832
Mr = 407.29	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1805 reflections
a = 12.5250 (18) Å	θ = 2.4–20.5°
b = 7.8885 (12) Å	µ = 2.29 mm−1
c = 19.143 (3) Å	T = 273 K
β = 106.812 (3)°	Block, colourless
V = 1810.5 (5) Å3	0.10 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2586 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
phi and ω scans	θmax = 23.3°, θmin = 1.7°
Absorption correction: numerical (SADABS; Bruker, 2007)	h = −12→13
Tmin = 0.804, Tmax = 0.838	k = −7→8
7291 measured reflections	l = −21→21

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0807P)2 + 0.9145P] where P = (Fo2 + 2Fc2)/3
2586 reflections	(Δ/σ)max = 0.006
236 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.94299 (6)	−0.03797 (10)	1.18603 (3)	0.1051 (4)
C13	0.6602 (3)	0.0719 (6)	1.0485 (2)	0.0529 (11)
C10	0.6311 (3)	0.3699 (6)	0.9720 (2)	0.0556 (11)
H10	0.6135	0.4696	0.9451	0.067*
O1	0.6717 (4)	−0.0722 (4)	1.08778 (19)	0.0844 (11)
H1	0.6952	−0.1476	1.0667	0.127*
C9	0.6706 (3)	0.2331 (5)	0.9423 (2)	0.0456 (10)
C12	0.6440 (3)	0.2212 (6)	1.0841 (2)	0.0548 (11)
C5	0.8972 (3)	0.2809 (7)	1.0081 (2)	0.0585 (12)
C11	0.6170 (3)	0.3618 (6)	1.0413 (3)	0.0624 (13)
H11	0.5882	0.4556	1.0591	0.075*
C8	0.7383 (3)	0.2704 (5)	0.8900 (2)	0.0546 (11)
H8A	0.7219	0.3845	0.8710	0.066*
H8B	0.7164	0.1924	0.8491	0.066*
C14	0.6714 (3)	0.0746 (5)	0.9773 (2)	0.0486 (10)
C2	0.8655 (3)	0.3001 (7)	1.1481 (2)	0.0579 (12)
C4	0.8811 (4)	0.4355 (7)	1.0375 (3)	0.0698 (14)
H4	0.8816	0.5345	1.0113	0.084*
C6	0.9229 (3)	0.1463 (7)	1.0567 (2)	0.0608 (12)
H6	0.9494	0.0460	1.0423	0.073*
C3	0.8642 (4)	0.4442 (7)	1.1062 (3)	0.0680 (14)
H3	0.8517	0.5493	1.1244	0.082*
C16	0.6713 (4)	−0.1147 (5)	0.8667 (2)	0.0587 (12)
C15	0.6967 (4)	−0.0862 (6)	0.9465 (3)	0.0661 (13)
O2	0.7342 (5)	−0.2069 (5)	0.9862 (2)	0.1206 (17)
C7	0.8650 (4)	0.2539 (7)	0.9266 (2)	0.0744 (15)
H7A	0.8892	0.1419	0.9167	0.089*
H7B	0.9038	0.3363	0.9052	0.089*
C17	0.7418 (5)	−0.2153 (6)	0.8396 (3)	0.0806 (15)
H17	0.8073	−0.2593	0.8706	0.097*
C20	0.5464 (5)	−0.0899 (8)	0.7459 (3)	0.0811 (16)
H20	0.4804	−0.0479	0.7146	0.097*
C21	0.5745 (4)	−0.0538 (6)	0.8193 (3)	0.0666 (14)
H21	0.5271	0.0129	0.8372	0.080*
C1	0.9105 (3)	0.1569 (6)	1.1249 (2)	0.0586 (12)
C19	0.6139 (6)	−0.1852 (8)	0.7194 (3)	0.0922 (19)
H19	0.5946	−0.2089	0.6697	0.111*
C18	0.7114 (7)	−0.2484 (7)	0.7647 (4)	0.096 (2)
H18	0.7577	−0.3139	0.7454	0.115*
C22	0.6778 (4)	0.2271 (7)	1.1667 (2)	0.0710 (14)
H22A	0.6724	0.1138	1.1851	0.085*
H22B	0.6257	0.2987	1.1819	0.085*
C23	0.7980 (4)	0.2950 (7)	1.2014 (2)	0.0724 (14)
H23A	0.7938	0.4083	1.2201	0.087*
H23B	0.8355	0.2231	1.2423	0.087*

	U11	U22	U33	U12	U13	U23
Br1	0.1093 (6)	0.1234 (6)	0.0873 (5)	0.0489 (4)	0.0358 (4)	0.0560 (4)
C13	0.055 (3)	0.053 (3)	0.051 (3)	−0.009 (2)	0.016 (2)	0.004 (2)
C10	0.052 (3)	0.046 (3)	0.059 (3)	0.008 (2)	0.000 (2)	0.000 (2)
O1	0.132 (3)	0.060 (2)	0.068 (2)	−0.011 (2)	0.040 (2)	0.0151 (18)
C9	0.050 (2)	0.038 (2)	0.043 (2)	0.0016 (18)	0.0045 (19)	−0.0004 (19)
C12	0.043 (2)	0.070 (3)	0.054 (3)	0.000 (2)	0.018 (2)	−0.008 (2)
C5	0.040 (2)	0.081 (4)	0.056 (3)	0.003 (2)	0.016 (2)	0.010 (3)
C11	0.051 (3)	0.061 (3)	0.071 (3)	0.015 (2)	0.011 (2)	−0.016 (3)
C8	0.074 (3)	0.043 (2)	0.043 (2)	−0.003 (2)	0.011 (2)	0.0063 (19)
C14	0.058 (3)	0.042 (3)	0.044 (2)	−0.0009 (19)	0.012 (2)	−0.0047 (19)
C2	0.046 (3)	0.074 (3)	0.047 (3)	−0.002 (2)	0.003 (2)	−0.007 (2)
C4	0.063 (3)	0.070 (4)	0.071 (3)	−0.015 (3)	0.011 (3)	0.014 (3)
C6	0.049 (3)	0.080 (4)	0.057 (3)	0.022 (2)	0.020 (2)	0.010 (3)
C3	0.061 (3)	0.065 (3)	0.070 (3)	−0.010 (2)	0.007 (3)	−0.018 (3)
C16	0.086 (3)	0.034 (2)	0.061 (3)	−0.008 (2)	0.029 (3)	−0.009 (2)
C15	0.098 (4)	0.033 (3)	0.067 (3)	0.004 (2)	0.024 (3)	0.002 (2)
O2	0.235 (5)	0.045 (2)	0.079 (3)	0.041 (3)	0.040 (3)	0.011 (2)
C7	0.068 (3)	0.107 (4)	0.055 (3)	0.014 (3)	0.028 (3)	0.018 (3)
C17	0.110 (4)	0.049 (3)	0.094 (4)	0.002 (3)	0.047 (3)	−0.007 (3)
C20	0.095 (4)	0.080 (4)	0.071 (4)	−0.032 (3)	0.027 (3)	−0.023 (3)
C21	0.078 (3)	0.063 (3)	0.065 (3)	−0.019 (3)	0.030 (3)	−0.017 (3)
C1	0.045 (2)	0.080 (4)	0.049 (3)	0.010 (2)	0.011 (2)	0.016 (2)
C19	0.133 (6)	0.076 (4)	0.076 (4)	−0.037 (4)	0.042 (4)	−0.024 (3)
C18	0.157 (6)	0.052 (4)	0.111 (5)	−0.018 (4)	0.092 (5)	−0.029 (3)
C22	0.069 (3)	0.094 (4)	0.057 (3)	0.000 (3)	0.029 (2)	−0.014 (3)
C23	0.070 (3)	0.098 (4)	0.050 (3)	−0.001 (3)	0.019 (2)	−0.014 (3)

Br1—C1	1.903 (5)	C6—C1	1.362 (6)
C13—O1	1.348 (5)	C6—H6	0.9300
C13—C12	1.405 (6)	C3—H3	0.9300
C13—C14	1.411 (6)	C16—C21	1.374 (6)
C10—C9	1.376 (6)	C16—C17	1.394 (7)
C10—C11	1.390 (6)	C16—C15	1.484 (6)
C10—H10	0.9300	C15—O2	1.225 (5)
O1—H1	0.8200	C15—O2	1.225 (5)
C9—C14	1.418 (6)	O2—O2	0.000 (11)
C9—C8	1.516 (6)	C7—H7A	0.9700
C12—C11	1.362 (6)	C7—H7B	0.9700
C12—C22	1.513 (6)	C17—C18	1.397 (8)
C5—C4	1.383 (7)	C17—H17	0.9300
C5—C6	1.387 (6)	C20—C19	1.336 (8)
C5—C7	1.508 (6)	C20—C21	1.377 (6)
C11—H11	0.9300	C20—H20	0.9300
C8—C7	1.544 (6)	C21—H21	0.9300
C8—H8A	0.9700	C19—C18	1.370 (9)
C8—H8B	0.9700	C19—H19	0.9300
C14—C15	1.472 (6)	C18—H18	0.9300
C2—C3	1.389 (7)	C22—C23	1.554 (7)
C2—C1	1.391 (6)	C22—H22A	0.9700
C2—C23	1.503 (6)	C22—H22B	0.9700
C4—C3	1.392 (7)	C23—H23A	0.9700
C4—H4	0.9300	C23—H23B	0.9700
O1—C13—C12	116.4 (4)	O2—C15—O2	0.0 (4)
O1—C13—C14	121.8 (4)	O2—C15—C14	120.6 (4)
C12—C13—C14	121.7 (4)	O2—C15—C14	120.6 (4)
C9—C10—C11	121.2 (4)	O2—C15—C16	116.8 (4)
C9—C10—H10	119.4	O2—C15—C16	116.8 (4)
C11—C10—H10	119.4	C14—C15—C16	122.4 (4)
C13—O1—H1	109.5	O2—O2—C15	0 (10)
C10—C9—C14	116.8 (4)	C5—C7—C8	113.0 (4)
C10—C9—C8	117.2 (4)	C5—C7—H7A	109.0
C14—C9—C8	123.7 (4)	C8—C7—H7A	109.0
C11—C12—C13	115.8 (4)	C5—C7—H7B	109.0
C11—C12—C22	123.3 (4)	C8—C7—H7B	109.0
C13—C12—C22	119.7 (4)	H7A—C7—H7B	107.8
C4—C5—C6	115.7 (4)	C16—C17—C18	118.3 (6)
C4—C5—C7	121.3 (5)	C16—C17—H17	120.8
C6—C5—C7	121.8 (5)	C18—C17—H17	120.8
C12—C11—C10	122.3 (4)	C19—C20—C21	120.0 (6)
C12—C11—H11	118.8	C19—C20—H20	120.0
C10—C11—H11	118.8	C21—C20—H20	120.0
C9—C8—C7	112.4 (3)	C16—C21—C20	121.2 (5)
C9—C8—H8A	109.1	C16—C21—H21	119.4
C7—C8—H8A	109.1	C20—C21—H21	119.4
C9—C8—H8B	109.1	C6—C1—C2	121.7 (4)
C7—C8—H8B	109.1	C6—C1—Br1	118.4 (4)
H8A—C8—H8B	107.9	C2—C1—Br1	119.6 (3)
C13—C14—C9	118.8 (4)	C20—C19—C18	120.7 (6)
C13—C14—C15	117.9 (4)	C20—C19—H19	119.6
C9—C14—C15	122.9 (4)	C18—C19—H19	119.6
C3—C2—C1	114.8 (4)	C19—C18—C17	120.7 (6)
C3—C2—C23	120.0 (5)	C19—C18—H18	119.7
C1—C2—C23	123.7 (5)	C17—C18—H18	119.7
C5—C4—C3	120.6 (5)	C12—C22—C23	113.6 (4)
C5—C4—H4	119.7	C12—C22—H22A	108.8
C3—C4—H4	119.7	C23—C22—H22A	108.8
C1—C6—C5	121.8 (5)	C12—C22—H22B	108.8
C1—C6—H6	119.1	C23—C22—H22B	108.8
C5—C6—H6	119.1	H22A—C22—H22B	107.7
C2—C3—C4	121.7 (5)	C2—C23—C22	112.6 (4)
C2—C3—H3	119.2	C2—C23—H23A	109.1
C4—C3—H3	119.2	C22—C23—H23A	109.1
C21—C16—C17	119.1 (5)	C2—C23—H23B	109.1
C21—C16—C15	120.8 (4)	C22—C23—H23B	109.1
C17—C16—C15	120.0 (5)	H23A—C23—H23B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.81	2.530 (5)	146
C4—H4···O2i	0.93	2.70	3.356 (7)	128
C19—H19···O1ii	0.93	2.69	3.404 (7)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.81	2.530 (5)	146
C4—H4⋯O2i	0.93	2.70	3.356 (7)	128
C19—H19⋯O1ii	0.93	2.69	3.404 (7)	134

Symmetry codes: (i) ; (ii) .