5-Benzoyl-13-bromo-4-hy­droxy[2.2]paracyclo­phane

Ma, K.; Duan, W.; He, F.; Ma, Y.

doi:10.1107/S1600536812013803

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1380

doi:10.1107/S1600536812013803

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5-Benzoyl-13-bromo-4-hydroxy[2.2]paracyclophane

Kelin Ma,^a Wenzeng Duan,^a,^b Fuyan He ^a and Yudao Ma ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Taishan University, Tai'an 27012, People's Republic of China
^*Correspondence e-mail: ydma@sdu.edu.cn

(Received 13 March 2012; accepted 30 March 2012; online 13 April 2012)

The title compound, C₂₃H₁₉BrO₂, was synthesized from 13-bromo-4-hydroxy[2.2]paracyclophane and benzoyl chloride. The hydroxy and carbonyl groups are involved in intramolecular O—H⋯O hydrogen bonding. The crystal packing exhibits weak C—H⋯O interactions, which link the molecules 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_r = 407.29
Monoclinic, P 2₁ /c
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
θ_max = 23.3°

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.147
S = 1.04
2586 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.74 e Å⁻³

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) x, y+1, z; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013803/cv5263sup1.cif

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

checkCIF report

Comment top

The planar chiral Schiff bases have been used in many asymmetric reactions (Danilova et al., 2003). [2. 2]Paracyclophane present planar chirality due to its configurationally rigid structure (Hong et al., 2011). The salicyaldehyde derivative based on [2. 2]paracyclophane is the parent compound of various Schiff base ligands (Fache et al., 2000). We reported here the crystal structure of the title compound (I), which is a derivative of [2.2]paracyclophane.

In (I) (Fig. 1), all bond lengths and angles are normal and in agreement with those observed in the related structure (Hong et al., 2011). The mean planes A (C16-C21), B (C16/C15/O2), C (O2/C15/C14), D(C9-C14) and E (C1-C6) form the following dihedral angles: A/B 41.1 (2)°, C/D=18.4 (2)°, B/C=4.1 (2)° and D/E=1.6 (2)°. The hydroxy and carbonyl groups are involved in O—H···O hydrogen bonding (Table 1).

The crystal packing exhibits weak intermolecular C—H···O interactions (Table 1), which link the molecules into sheets parallel to bc palne.

Related literature top

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 top

The title compound was prepared by the method reported by Xin et al. (2010). The crystals were obtained by recrystallization from EtOH.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atom numbering scheme and 50% probabilty displacement ellipsoids. The H atoms are omitted for clarity.

5-Benzoyl-13-bromo-4-hydroxy[2.2]paracyclophane top

Crystal data top

C₂₃H₁₉BrO₂	F(000) = 832
M_r = 407.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0807P)² + 0.9145P] where P = (F_o² + 2F_c²)/3
2586 reflections	(Δ/σ)_max = 0.006
236 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₂₃H₁₉BrO₂	V = 1810.5 (5) Å³
M_r = 407.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5250 (18) Å	µ = 2.29 mm⁻¹
b = 7.8885 (12) Å	T = 273 K
c = 19.143 (3) Å	0.10 × 0.10 × 0.08 mm
β = 106.812 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2586 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2007)	1810 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.838	R_int = 0.033
7291 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
2586 reflections	Δρ_min = −0.74 e Å⁻³
236 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉BrO₂
M_r	407.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	12.5250 (18), 7.8885 (12), 19.143 (3)
β (°)	106.812 (3)
V (Å³)	1810.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.29
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Numerical (SADABS; Bruker, 2007)
T_min, T_max	0.804, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	7291, 2586, 1810
R_int	0.033
θ_max (°)	23.3
(sin θ/λ)_max (Å⁻¹)	0.556

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.147, 1.04
No. of reflections	2586
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.74

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.81	2.530 (5)	146.3
C4—H4···O2ⁱ	0.93	2.70	3.356 (7)	128.3
C19—H19···O1ⁱⁱ	0.93	2.69	3.404 (7)	133.9

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

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant No. 20671059) and the Department of Science and Technology of Shandong Province is gratefully acknowledged.

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