1-(4-Meth-oxy-phen-yl)ethane-1,2-diyl 1,1'-biphenyl-2,2'-dicarboxyl-ate.

In the title mol-ecule, C(23)H(18)O(5), the meth-oxy-substituted benzene ring makes dihedral angles of 65.12 (4) and 88.55 (4)° with the other two benzene rings. These two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, mol-ecules are linked into inversion dimers by pairs of weak C-H⋯O hydrogen bonds.

Related literature

For the background to this study has been set out in the preceding paper, see: Fun et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the preparation, see: Wu et al. (2012 ▶).

Experimental

Crystal data

C23H18O5

M = 374.37

Monoclinic,

a = 14.0049 (5) Å

b = 10.8637 (4) Å

c = 12.7190 (5) Å

β = 110.150 (1)°

V = 1816.69 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.50 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.969

30595 measured reflections

8040 independent reflections

6872 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.03

8040 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201848X/is5123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201848X/is5123Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201848X/is5123Isup3.cml

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

C23H18O5	F(000) = 784
Mr = 374.37	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9888 reflections
a = 14.0049 (5) Å	θ = 3.3–35.1°
b = 10.8637 (4) Å	µ = 0.10 mm−1
c = 12.7190 (5) Å	T = 100 K
β = 110.150 (1)°	Block, colourless
V = 1816.69 (12) Å3	0.50 × 0.37 × 0.33 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	8040 independent reflections
Radiation source: fine-focus sealed tube	6872 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 35.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.954, Tmax = 0.969	k = −17→16
30595 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0706P)2 + 0.3453P] where P = (Fo2 + 2Fc2)/3
8040 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > 2sigma(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
O1	0.38784 (4)	0.55150 (5)	0.14424 (4)	0.01591 (10)
O2	0.35057 (4)	0.34260 (5)	0.01861 (5)	0.01878 (11)
O3	0.35878 (4)	0.61128 (5)	−0.03585 (5)	0.01878 (11)
O4	0.23791 (5)	0.35189 (5)	0.11150 (5)	0.02007 (11)
O5	0.77642 (5)	0.51575 (6)	0.57884 (5)	0.02188 (12)
C1	0.33248 (5)	0.60283 (6)	0.04471 (6)	0.01410 (11)
C2	0.23425 (5)	0.64784 (6)	0.05242 (6)	0.01326 (11)
C3	0.24048 (5)	0.74160 (6)	0.12951 (6)	0.01596 (12)
H3A	0.3038	0.7721	0.1731	0.019*
C4	0.15308 (6)	0.78980 (7)	0.14184 (7)	0.01838 (13)
H4A	0.1576	0.8539	0.1918	0.022*
C5	0.05903 (6)	0.74156 (7)	0.07911 (7)	0.01791 (13)
H5A	0.0002	0.7724	0.0877	0.021*
C6	0.05267 (5)	0.64697 (6)	0.00326 (6)	0.01502 (12)
H6A	−0.0108	0.6148	−0.0377	0.018*
C7	0.13932 (5)	0.59887 (6)	−0.01318 (6)	0.01314 (11)
C8	0.12481 (5)	0.50195 (6)	−0.10053 (6)	0.01377 (11)
C9	0.04937 (5)	0.52047 (7)	−0.20515 (6)	0.01666 (12)
H9A	0.0091	0.5907	−0.2169	0.020*
C10	0.03313 (6)	0.43626 (7)	−0.29216 (6)	0.01981 (13)
H10A	−0.0186	0.4495	−0.3604	0.024*
C11	0.09433 (6)	0.33242 (7)	−0.27690 (7)	0.02003 (13)
H11A	0.0852	0.2775	−0.3356	0.024*
C12	0.16915 (6)	0.31098 (7)	−0.17363 (7)	0.01812 (13)
H12A	0.2103	0.2416	−0.1633	0.022*
C13	0.18276 (5)	0.39331 (6)	−0.08526 (6)	0.01456 (11)
C14	0.25758 (6)	0.36052 (6)	0.02653 (6)	0.01598 (12)
C15	0.43566 (6)	0.34300 (7)	0.12253 (7)	0.02087 (14)
H15A	0.4893	0.2904	0.1161	0.025*
H15B	0.4146	0.3116	0.1825	0.025*
C16	0.47489 (5)	0.47470 (7)	0.14896 (6)	0.01735 (12)
H16A	0.5039	0.5029	0.0932	0.021*
C17	0.55272 (5)	0.48569 (7)	0.26440 (6)	0.01667 (12)
C18	0.53402 (6)	0.43948 (8)	0.35776 (7)	0.02047 (14)
H18A	0.4718	0.4023	0.3484	0.025*
C19	0.60657 (6)	0.44787 (8)	0.46475 (6)	0.01999 (13)
H19A	0.5933	0.4160	0.5262	0.024*
C20	0.69930 (5)	0.50455 (7)	0.47858 (6)	0.01664 (12)
C21	0.71830 (6)	0.55306 (6)	0.38612 (6)	0.01783 (13)
H21A	0.7798	0.5922	0.3957	0.021*
C22	0.64573 (6)	0.54311 (6)	0.28016 (6)	0.01736 (12)
H22A	0.6591	0.5750	0.2188	0.021*
C23	0.76498 (7)	0.45148 (10)	0.67193 (7)	0.02796 (18)
H23A	0.8262	0.4595	0.7357	0.042*
H23B	0.7521	0.3660	0.6533	0.042*
H23C	0.7089	0.4858	0.6892	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0142 (2)	0.0186 (2)	0.0154 (2)	0.00415 (17)	0.00568 (17)	0.00102 (17)
O2	0.0156 (2)	0.0204 (2)	0.0190 (2)	0.00381 (18)	0.00424 (18)	−0.00265 (18)
O3	0.0179 (2)	0.0224 (2)	0.0184 (2)	0.00192 (19)	0.00934 (19)	0.00145 (19)
O4	0.0244 (3)	0.0174 (2)	0.0200 (2)	0.00093 (19)	0.0096 (2)	0.00254 (18)
O5	0.0199 (3)	0.0270 (3)	0.0163 (2)	−0.0030 (2)	0.0032 (2)	−0.0001 (2)
C1	0.0129 (3)	0.0133 (2)	0.0162 (3)	0.0003 (2)	0.0052 (2)	−0.0004 (2)
C2	0.0133 (3)	0.0122 (2)	0.0153 (3)	0.00065 (19)	0.0062 (2)	0.00129 (19)
C3	0.0164 (3)	0.0141 (2)	0.0187 (3)	−0.0004 (2)	0.0078 (2)	−0.0016 (2)
C4	0.0202 (3)	0.0152 (3)	0.0227 (3)	0.0006 (2)	0.0112 (3)	−0.0023 (2)
C5	0.0175 (3)	0.0165 (3)	0.0229 (3)	0.0027 (2)	0.0110 (2)	0.0014 (2)
C6	0.0137 (3)	0.0149 (2)	0.0179 (3)	0.0014 (2)	0.0072 (2)	0.0027 (2)
C7	0.0135 (3)	0.0124 (2)	0.0144 (3)	0.00076 (19)	0.0058 (2)	0.00167 (19)
C8	0.0134 (3)	0.0141 (2)	0.0148 (3)	−0.00113 (19)	0.0061 (2)	0.0003 (2)
C9	0.0153 (3)	0.0190 (3)	0.0154 (3)	−0.0012 (2)	0.0049 (2)	0.0015 (2)
C10	0.0185 (3)	0.0242 (3)	0.0160 (3)	−0.0055 (2)	0.0050 (2)	−0.0011 (2)
C11	0.0206 (3)	0.0215 (3)	0.0189 (3)	−0.0072 (2)	0.0080 (3)	−0.0057 (2)
C12	0.0185 (3)	0.0157 (3)	0.0213 (3)	−0.0028 (2)	0.0084 (2)	−0.0038 (2)
C13	0.0143 (3)	0.0137 (2)	0.0163 (3)	−0.0012 (2)	0.0061 (2)	−0.0007 (2)
C14	0.0170 (3)	0.0120 (2)	0.0189 (3)	0.0012 (2)	0.0062 (2)	−0.0005 (2)
C15	0.0183 (3)	0.0196 (3)	0.0211 (3)	0.0057 (2)	0.0022 (3)	−0.0017 (2)
C16	0.0142 (3)	0.0214 (3)	0.0165 (3)	0.0049 (2)	0.0053 (2)	−0.0004 (2)
C17	0.0143 (3)	0.0199 (3)	0.0160 (3)	0.0029 (2)	0.0054 (2)	0.0003 (2)
C18	0.0143 (3)	0.0304 (4)	0.0174 (3)	−0.0009 (3)	0.0065 (2)	0.0002 (3)
C19	0.0170 (3)	0.0284 (3)	0.0159 (3)	−0.0006 (3)	0.0074 (2)	0.0004 (2)
C20	0.0160 (3)	0.0176 (3)	0.0159 (3)	0.0011 (2)	0.0048 (2)	−0.0010 (2)
C21	0.0181 (3)	0.0161 (3)	0.0193 (3)	−0.0016 (2)	0.0065 (2)	0.0001 (2)
C22	0.0188 (3)	0.0163 (3)	0.0176 (3)	0.0010 (2)	0.0071 (2)	0.0018 (2)
C23	0.0225 (4)	0.0423 (5)	0.0169 (3)	−0.0023 (3)	0.0040 (3)	0.0039 (3)

O1—C1	1.3558 (9)	C10—H10A	0.9300
O1—C16	1.4613 (9)	C11—C12	1.3890 (11)
O2—C14	1.3543 (9)	C11—H11A	0.9300
O2—C15	1.4429 (9)	C12—C13	1.3971 (10)
O3—C1	1.2058 (9)	C12—H12A	0.9300
O4—C14	1.2073 (9)	C13—C14	1.4901 (10)
O5—C20	1.3633 (9)	C15—C16	1.5281 (11)
O5—C23	1.4303 (11)	C15—H15A	0.9700
C1—C2	1.4948 (9)	C15—H15B	0.9700
C2—C3	1.3955 (10)	C16—C17	1.5019 (10)
C2—C7	1.4080 (9)	C16—H16A	0.9800
C3—C4	1.3891 (10)	C17—C18	1.3946 (11)
C3—H3A	0.9300	C17—C22	1.3950 (10)
C4—C5	1.3864 (11)	C18—C19	1.3928 (11)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.3913 (10)	C19—C20	1.3925 (11)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.4016 (9)	C20—C21	1.3954 (11)
C6—H6A	0.9300	C21—C22	1.3846 (10)
C7—C8	1.4928 (10)	C21—H21A	0.9300
C8—C9	1.3995 (10)	C22—H22A	0.9300
C8—C13	1.4074 (10)	C23—H23A	0.9600
C9—C10	1.3929 (11)	C23—H23B	0.9600
C9—H9A	0.9300	C23—H23C	0.9600
C10—C11	1.3893 (12)
C1—O1—C16	118.28 (6)	C8—C13—C14	120.98 (6)
C14—O2—C15	116.31 (6)	O4—C14—O2	125.25 (7)
C20—O5—C23	116.88 (6)	O4—C14—C13	124.78 (7)
O3—C1—O1	125.52 (6)	O2—C14—C13	109.97 (6)
O3—C1—C2	126.03 (6)	O2—C15—C16	108.98 (6)
O1—C1—C2	108.45 (6)	O2—C15—H15A	109.9
C3—C2—C7	120.66 (6)	C16—C15—H15A	109.9
C3—C2—C1	116.65 (6)	O2—C15—H15B	109.9
C7—C2—C1	122.68 (6)	C16—C15—H15B	109.9
C4—C3—C2	120.67 (7)	H15A—C15—H15B	108.3
C4—C3—H3A	119.7	O1—C16—C17	108.00 (6)
C2—C3—H3A	119.7	O1—C16—C15	107.09 (6)
C5—C4—C3	119.48 (7)	C17—C16—C15	111.98 (6)
C5—C4—H4A	120.3	O1—C16—H16A	109.9
C3—C4—H4A	120.3	C17—C16—H16A	109.9
C4—C5—C6	119.97 (7)	C15—C16—H16A	109.9
C4—C5—H5A	120.0	C18—C17—C22	118.59 (7)
C6—C5—H5A	120.0	C18—C17—C16	121.19 (7)
C5—C6—C7	121.80 (7)	C22—C17—C16	120.22 (7)
C5—C6—H6A	119.1	C19—C18—C17	121.36 (7)
C7—C6—H6A	119.1	C19—C18—H18A	119.3
C6—C7—C2	117.39 (6)	C17—C18—H18A	119.3
C6—C7—C8	118.10 (6)	C20—C19—C18	119.15 (7)
C2—C7—C8	124.49 (6)	C20—C19—H19A	120.4
C9—C8—C13	117.54 (6)	C18—C19—H19A	120.4
C9—C8—C7	118.09 (6)	O5—C20—C19	124.16 (7)
C13—C8—C7	124.37 (6)	O5—C20—C21	115.78 (7)
C10—C9—C8	121.61 (7)	C19—C20—C21	120.06 (7)
C10—C9—H9A	119.2	C22—C21—C20	120.11 (7)
C8—C9—H9A	119.2	C22—C21—H21A	119.9
C11—C10—C9	119.89 (7)	C20—C21—H21A	119.9
C11—C10—H10A	120.1	C21—C22—C17	120.71 (7)
C9—C10—H10A	120.1	C21—C22—H22A	119.6
C12—C11—C10	119.76 (7)	C17—C22—H22A	119.6
C12—C11—H11A	120.1	O5—C23—H23A	109.5
C10—C11—H11A	120.1	O5—C23—H23B	109.5
C11—C12—C13	120.18 (7)	H23A—C23—H23B	109.5
C11—C12—H12A	119.9	O5—C23—H23C	109.5
C13—C12—H12A	119.9	H23A—C23—H23C	109.5
C12—C13—C8	120.90 (6)	H23B—C23—H23C	109.5
C12—C13—C14	118.09 (6)
C16—O1—C1—O3	−15.26 (10)	C9—C8—C13—C14	−174.01 (6)
C16—O1—C1—C2	165.24 (6)	C7—C8—C13—C14	6.70 (10)
O3—C1—C2—C3	−115.76 (8)	C15—O2—C14—O4	−15.77 (10)
O1—C1—C2—C3	63.74 (8)	C15—O2—C14—C13	163.90 (6)
O3—C1—C2—C7	64.78 (10)	C12—C13—C14—O4	−122.73 (8)
O1—C1—C2—C7	−115.72 (7)	C8—C13—C14—O4	55.03 (10)
C7—C2—C3—C4	−1.00 (10)	C12—C13—C14—O2	57.60 (8)
C1—C2—C3—C4	179.52 (6)	C8—C13—C14—O2	−124.64 (7)
C2—C3—C4—C5	1.90 (11)	C14—O2—C15—C16	−89.13 (8)
C3—C4—C5—C6	−1.03 (11)	C1—O1—C16—C17	149.64 (6)
C4—C5—C6—C7	−0.75 (11)	C1—O1—C16—C15	−89.59 (7)
C5—C6—C7—C2	1.62 (10)	O2—C15—C16—O1	52.88 (8)
C5—C6—C7—C8	−176.89 (6)	O2—C15—C16—C17	171.09 (6)
C3—C2—C7—C6	−0.74 (10)	O1—C16—C17—C18	66.97 (9)
C1—C2—C7—C6	178.70 (6)	C15—C16—C17—C18	−50.70 (9)
C3—C2—C7—C8	177.67 (6)	O1—C16—C17—C22	−112.89 (7)
C1—C2—C7—C8	−2.89 (10)	C15—C16—C17—C22	129.45 (7)
C6—C7—C8—C9	45.82 (9)	C22—C17—C18—C19	−1.10 (12)
C2—C7—C8—C9	−132.57 (7)	C16—C17—C18—C19	179.04 (7)
C6—C7—C8—C13	−134.90 (7)	C17—C18—C19—C20	0.54 (12)
C2—C7—C8—C13	46.71 (10)	C23—O5—C20—C19	8.11 (11)
C13—C8—C9—C10	−1.31 (10)	C23—O5—C20—C21	−171.16 (7)
C7—C8—C9—C10	178.02 (6)	C18—C19—C20—O5	−178.66 (7)
C8—C9—C10—C11	−1.62 (11)	C18—C19—C20—C21	0.58 (12)
C9—C10—C11—C12	2.22 (11)	O5—C20—C21—C22	178.19 (7)
C10—C11—C12—C13	0.14 (11)	C19—C20—C21—C22	−1.11 (11)
C11—C12—C13—C8	−3.16 (11)	C20—C21—C22—C17	0.54 (11)
C11—C12—C13—C14	174.61 (7)	C18—C17—C22—C21	0.55 (11)
C9—C8—C13—C12	3.69 (10)	C16—C17—C22—C21	−179.59 (6)
C7—C8—C13—C12	−175.60 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3i	0.98	2.60	3.2676 (10)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O3i	0.98	2.60	3.2676 (10)	126

Symmetry code: (i) .