Structural characterization, gelation ability, and energy-framework analysis of two bis­(long-chain ester)-substituted 4,4′-biphenyl compounds

There are few examples of single-crystal structure determinations of gelators, as gel formation requires that the dissolved gelator self-assemble into a three-dimensional network structure incorporating solvent via noncovalent inter­actions rather than self-assembly followed by crystallization. In the solid-state structures of the isostructural compounds 4,4′-bis­[5-(meth­oxy­carbonyl)pentyl­oxy]biphenyl (BBO6-Me), C₂₆H₃₄O₆, and 4,4′-bis­[5-(eth­oxy­carbonyl)pentyl­oxy]biphenyl (BBO6-Et), C₂₈H₃₈O₆, the mol­ecules sit on a crystallographically imposed center of symmetry, resulting in strictly coplanar phenyl rings. BBO6-Me behaves as an organo­gelator in various alcohol solvents, whereas BBO6-Et does not. The extended structure reveals bundles of mol­ecules that form a columnar super­structure. Framework-energy calculations reveal much stronger inter­action energies within the columns (−52 to −78 kJ mol⁻¹) than between columns (−2 to −16 kJ mol⁻¹). The intra­columnar inter­actions are dominated by a dispersion component, whereas the inter­columnar inter­actions have a substantial electro­static component.

Computing details

For both structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

4,4'-Bis[5-(methoxycarbonyl)pentyloxy]biphenyl (BBO6-Me)

Crystal data

C26H34O6	F(000) = 476
Mr = 442.53	Dx = 1.170 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.022 (9) Å	Cell parameters from 2862 reflections
b = 7.410 (3) Å	θ = 2.4–24.7°
c = 6.531 (2) Å	µ = 0.08 mm^−1
β = 94.377 (11)°	T = 200 K
V = 1255.7 (7) Å^3	Plate, clear colourless
Z = 2	0.60 × 0.30 × 0.08 mm

Data collection

Bruker SMART X2S benchtop diffractometer	2251 independent reflections
Radiation source: sealed microfocus tube	1378 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.063
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.4°, θmin = 2.9°
ω scans	h = −31→29
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→8
Tmin = 0.72, Tmax = 0.99	l = −7→7
14032 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.081	H-atom parameters constrained
wR(F^2) = 0.264	w = 1/[σ^2(Fo^2) + (0.124P)^2 + 0.9748P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2251 reflections	Δρmax = 0.56 e Å^−3
155 parameters	Δρmin = −0.22 e Å^−3
26 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (4)

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.

Refinement. Rotational disorder in the ester functional group was observed. The disorder involved both O atoms and the methyl group. The structure was refined employing a model with two positions for these atoms with occupancies of 0.76 (3):0.24 (3). The coordinates of the ester oxygen (O3) in both components were constrained to be equal and the U^ij components restrained to behave approximately isotropically. The ethyl C—C carbon bond length was restrained to 1.50 Å and the O—C(Ethyl) carbon bond length was restrained to 1.40 Å. All H atoms were located in difference Fourier maps, except for those associated with the components of the disorder models. H atoms were refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for the aromatic positions, C—H = 0.99 Å and Uiso(H) = 1.2 Ueq(C) for the methylene groups, and C—H = 0.98 Å and Uiso(H) = 1.5 Ueq(C) for the methyl groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.32457 (9)	0.4751 (3)	0.2478 (3)	0.0546 (7)
C1	0.37389 (12)	0.4925 (4)	0.1874 (4)	0.0430 (8)
C2	0.41439 (13)	0.5814 (5)	0.2950 (5)	0.0523 (9)
H2	0.4088	0.6414	0.42	0.063*
C3	0.46281 (13)	0.5831 (5)	0.2211 (5)	0.0508 (9)
H3	0.4899	0.6445	0.2979	0.061*
C4	0.47346 (11)	0.4986 (4)	0.0387 (4)	0.0381 (7)
C5	0.43153 (12)	0.4134 (4)	−0.0689 (4)	0.0452 (8)
H5	0.4367	0.3561	−0.1958	0.054*
C6	0.38343 (13)	0.4100 (4)	0.0024 (4)	0.0469 (8)
H6	0.3561	0.3504	−0.0754	0.056*
C7	0.31436 (13)	0.5369 (5)	0.4482 (5)	0.0535 (9)
H7A	0.3154	0.6704	0.4536	0.064*
H7B	0.3406	0.4891	0.5521	0.064*
C8	0.26140 (14)	0.4694 (5)	0.4907 (5)	0.0574 (10)
H8A	0.2617	0.3358	0.4905	0.069*
H8B	0.2363	0.5096	0.3784	0.069*
C9	0.24359 (13)	0.5356 (5)	0.6954 (5)	0.0551 (9)
H9A	0.2677	0.4895	0.808	0.066*
H9B	0.2453	0.669	0.6986	0.066*
C10	0.18926 (14)	0.4771 (5)	0.7339 (5)	0.0580 (10)
H10A	0.1651	0.52	0.6197	0.07*
H10B	0.1877	0.3437	0.7361	0.07*
C11	0.17247 (16)	0.5497 (6)	0.9336 (6)	0.0732 (12)
H11A	0.1968	0.5053	1.0462	0.088*
H11B	0.1754	0.6829	0.9309	0.088*
C12	0.1200 (2)	0.5030 (7)	0.9826 (8)	0.0853 (14)
O2	0.0838 (5)	0.454 (2)	0.8610 (13)	0.121 (3)	0.76 (3)
O3	0.11170 (16)	0.5413 (6)	1.1752 (6)	0.1234 (15)	0.76 (3)
C13	0.0582 (4)	0.499 (3)	1.254 (2)	0.150 (5)	0.76 (3)
H13A	0.0311	0.5252	1.1458	0.225*	0.76 (3)
H13B	0.053	0.5745	1.3746	0.225*	0.76 (3)
H13C	0.0566	0.3716	1.2928	0.225*	0.76 (3)
O2B	0.0995 (12)	0.384 (6)	0.885 (5)	0.121 (3)	0.24 (3)
O3B	0.11170 (16)	0.5413 (6)	1.1752 (6)	0.1234 (15)	0.24 (3)
C13B	0.0572 (12)	0.589 (7)	1.264 (9)	0.150 (5)	0.24 (3)
H13D	0.0294	0.5677	1.1568	0.225*	0.24 (3)
H13E	0.0571	0.7158	1.3056	0.225*	0.24 (3)
H13F	0.0521	0.5119	1.3825	0.225*	0.24 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0559 (15)	0.0656 (17)	0.0422 (13)	−0.0037 (11)	0.0027 (10)	−0.0062 (11)
C1	0.0495 (19)	0.0391 (18)	0.0399 (17)	0.0042 (14)	0.0006 (13)	0.0035 (13)
C2	0.059 (2)	0.051 (2)	0.0465 (18)	−0.0052 (16)	0.0061 (15)	−0.0147 (15)
C3	0.054 (2)	0.047 (2)	0.0499 (19)	−0.0094 (15)	0.0003 (15)	−0.0143 (15)
C4	0.0508 (18)	0.0250 (16)	0.0374 (15)	−0.0006 (13)	−0.0049 (12)	0.0021 (12)
C5	0.055 (2)	0.0448 (19)	0.0343 (16)	−0.0020 (15)	−0.0029 (13)	−0.0037 (13)
C6	0.054 (2)	0.047 (2)	0.0380 (16)	−0.0028 (15)	−0.0074 (14)	−0.0030 (14)
C7	0.058 (2)	0.056 (2)	0.0455 (18)	0.0034 (16)	−0.0013 (15)	−0.0056 (16)
C8	0.061 (2)	0.059 (2)	0.052 (2)	−0.0010 (17)	0.0030 (16)	−0.0069 (17)
C9	0.053 (2)	0.060 (2)	0.051 (2)	0.0060 (16)	−0.0023 (15)	−0.0028 (16)
C10	0.055 (2)	0.060 (2)	0.058 (2)	−0.0008 (17)	0.0011 (16)	−0.0009 (17)
C11	0.066 (3)	0.091 (3)	0.063 (2)	−0.006 (2)	0.0078 (19)	−0.013 (2)
C12	0.073 (3)	0.098 (4)	0.086 (3)	−0.012 (3)	0.016 (2)	−0.005 (3)
O2	0.059 (5)	0.180 (9)	0.125 (4)	−0.022 (5)	0.015 (3)	−0.032 (5)
O3	0.107 (3)	0.166 (4)	0.102 (3)	−0.020 (3)	0.044 (2)	−0.030 (3)
C13	0.113 (5)	0.163 (11)	0.178 (7)	−0.059 (6)	0.042 (5)	0.022 (10)
O2B	0.059 (5)	0.180 (9)	0.125 (4)	−0.022 (5)	0.015 (3)	−0.032 (5)
O3B	0.107 (3)	0.166 (4)	0.102 (3)	−0.020 (3)	0.044 (2)	−0.030 (3)
C13B	0.113 (5)	0.163 (11)	0.178 (7)	−0.059 (6)	0.042 (5)	0.022 (10)

Geometric parameters (Å, º)

O1—C1	1.377 (4)	C9—H9A	0.99
O1—C7	1.431 (4)	C9—H9B	0.99
C1—C2	1.388 (4)	C10—C11	1.506 (5)
C1—C6	1.393 (4)	C10—H10A	0.99
C2—C3	1.383 (5)	C10—H10B	0.99
C2—H2	0.95	C11—C12	1.467 (6)
C3—C4	1.392 (4)	C11—H11A	0.99
C3—H3	0.95	C11—H11B	0.99
C4—C5	1.402 (4)	C12—O2B	1.19 (3)
C4—C4^i	1.506 (6)	C12—O2	1.238 (10)
C5—C6	1.369 (5)	C12—O3B	1.323 (6)
C5—H5	0.95	C12—O3	1.323 (6)
C6—H6	0.95	O3—C13	1.555 (8)
C7—C8	1.511 (5)	C13—H13A	0.98
C7—H7A	0.99	C13—H13B	0.98
C7—H7B	0.99	C13—H13C	0.98
C8—C9	1.529 (5)	O3B—C13B	1.610 (18)
C8—H8A	0.99	C13B—H13D	0.98
C8—H8B	0.99	C13B—H13E	0.98
C9—C10	1.518 (5)	C13B—H13F	0.98
C1—O1—C7	118.3 (2)	C8—C9—H9B	108.8
O1—C1—C2	126.0 (3)	H9A—C9—H9B	107.7
O1—C1—C6	116.0 (3)	C11—C10—C9	112.1 (3)
C2—C1—C6	118.0 (3)	C11—C10—H10A	109.2
C3—C2—C1	120.3 (3)	C9—C10—H10A	109.2
C3—C2—H2	119.9	C11—C10—H10B	109.2
C1—C2—H2	119.9	C9—C10—H10B	109.2
C2—C3—C4	122.7 (3)	H10A—C10—H10B	107.9
C2—C3—H3	118.6	C12—C11—C10	116.2 (4)
C4—C3—H3	118.6	C12—C11—H11A	108.2
C3—C4—C5	115.6 (3)	C10—C11—H11A	108.2
C3—C4—C4^i	121.9 (3)	C12—C11—H11B	108.2
C5—C4—C4^i	122.5 (3)	C10—C11—H11B	108.2
C6—C5—C4	122.4 (3)	H11A—C11—H11B	107.4
C6—C5—H5	118.8	O2B—C12—O3B	124.6 (16)
C4—C5—H5	118.8	O2—C12—O3	120.0 (6)
C5—C6—C1	121.0 (3)	O2B—C12—C11	116.4 (15)
C5—C6—H6	119.5	O2—C12—C11	127.2 (6)
C1—C6—H6	119.5	O3B—C12—C11	112.3 (4)
O1—C7—C8	107.3 (3)	O3—C12—C11	112.3 (4)
O1—C7—H7A	110.3	C12—O3—C13	119.3 (8)
C8—C7—H7A	110.3	O3—C13—H13A	109.5
O1—C7—H7B	110.3	O3—C13—H13B	109.5
C8—C7—H7B	110.3	H13A—C13—H13B	109.5
H7A—C7—H7B	108.5	O3—C13—H13C	109.5
C7—C8—C9	113.3 (3)	H13A—C13—H13C	109.5
C7—C8—H8A	108.9	H13B—C13—H13C	109.5
C9—C8—H8A	108.9	C12—O3B—C13B	127 (2)
C7—C8—H8B	108.9	O3B—C13B—H13D	109.5
C9—C8—H8B	108.9	O3B—C13B—H13E	109.5
H8A—C8—H8B	107.7	H13D—C13B—H13E	109.5
C10—C9—C8	113.7 (3)	O3B—C13B—H13F	109.5
C10—C9—H9A	108.8	H13D—C13B—H13F	109.5
C8—C9—H9A	108.8	H13E—C13B—H13F	109.5
C10—C9—H9B	108.8
C7—O1—C1—C2	−6.8 (5)	O1—C7—C8—C9	−176.3 (3)
C7—O1—C1—C6	172.1 (3)	C7—C8—C9—C10	176.8 (3)
O1—C1—C2—C3	177.4 (3)	C8—C9—C10—C11	−178.2 (3)
C6—C1—C2—C3	−1.5 (5)	C9—C10—C11—C12	178.9 (4)
C1—C2—C3—C4	0.3 (5)	C10—C11—C12—O2B	15 (3)
C2—C3—C4—C5	1.1 (5)	C10—C11—C12—O2	−20.9 (13)
C2—C3—C4—C4^i	−179.7 (3)	C10—C11—C12—O3B	167.8 (4)
C3—C4—C5—C6	−1.3 (4)	C10—C11—C12—O3	167.8 (4)
C4^i—C4—C5—C6	179.5 (3)	O2—C12—O3—C13	8.4 (19)
C4—C5—C6—C1	0.2 (5)	C11—C12—O3—C13	−179.5 (9)
O1—C1—C6—C5	−177.7 (3)	O2B—C12—O3B—C13B	−57 (4)
C2—C1—C6—C5	1.3 (5)	C11—C12—O3B—C13B	153 (2)
C1—O1—C7—C8	−169.0 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

Cg refers to the centroid of the symmetry-unique phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O2^ii	0.98	2.55	3.488 (16)	161
C6—H6···O1^iii	0.95	2.77	3.587 (4)	144
C5—H5···Cg^iii	0.95	2.91	3.678 (3)	139
C2—H2···Cg^iv	0.95	2.98	3.751 (4)	140

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

4,4'-Bis[5-(ethoxycarbonyl)pentyloxy]biphenyl (BBO6-Et)

Crystal data

C28H38O6	F(000) = 508
Mr = 470.58	Dx = 1.201 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.594 (7) Å	Cell parameters from 1805 reflections
b = 7.5344 (17) Å	θ = 2.3–24.9°
c = 6.5302 (14) Å	µ = 0.08 mm^−1
β = 95.872 (8)°	T = 200 K
V = 1301.6 (5) Å^3	Plate, clear colourless
Z = 2	0.50 × 0.50 × 0.05 mm

Data collection

Bruker SMART X2S benchtop diffractometer	2328 independent reflections
Radiation source: sealed microfocus tube	1374 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.057
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.3°, θmin = 1.5°
ω scans	h = −31→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→8
Tmin = 0.65, Tmax = 1.00	l = −7→7
7714 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.232	w = 1/[σ^2(Fo^2) + (0.1115P)^2 + 0.3294P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2328 reflections	Δρmax = 0.26 e Å^−3
164 parameters	Δρmin = −0.37 e Å^−3
34 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (4)

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.

Refinement. Rotational disorder in the ester functional group was observed. The disorder was modeled with two positions for the ethyl group with refined occupancies of 0.648 (15):0.352 (15). Similarity restraints based on the major-disorder components were employed and the anisotropic displacement parameters of corresponding atoms were constrained to be equal. All H atoms were located in difference Fourier maps, except for those associated with the components of the disorder models. H atoms were refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for the aromatic positions, C—H = 0.99 Å and Uiso(H) = 1.2 Ueq(C) for the methylene groups, and C—H = 0.98 Å and Uiso(H) = 1.5 Ueq(C) for the methyl groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.33045 (7)	0.4751 (3)	0.2409 (3)	0.0621 (6)
C1	0.37790 (11)	0.4917 (3)	0.1818 (4)	0.0497 (7)
C2	0.41746 (11)	0.5820 (4)	0.2898 (5)	0.0606 (8)
H2	0.4122	0.6426	0.4134	0.073*
C3	0.46432 (11)	0.5840 (4)	0.2182 (4)	0.0593 (8)
H3	0.4909	0.6462	0.2958	0.071*
C4	0.47493 (9)	0.4989 (3)	0.0362 (4)	0.0433 (6)
C5	0.43364 (10)	0.4116 (3)	−0.0682 (4)	0.0505 (7)
H5	0.4382	0.352	−0.1931	0.061*
C6	0.38696 (11)	0.4081 (4)	0.0014 (4)	0.0539 (7)
H6	0.3602	0.3468	−0.0761	0.065*
C7	0.32081 (11)	0.5378 (4)	0.4384 (4)	0.0604 (8)
H7A	0.3217	0.6691	0.4415	0.073*
H7B	0.3468	0.4925	0.5449	0.073*
C8	0.26938 (11)	0.4720 (4)	0.4791 (5)	0.0644 (8)
H8A	0.2699	0.3406	0.4827	0.077*
H8B	0.2445	0.5086	0.3637	0.077*
C9	0.25215 (12)	0.5395 (4)	0.6775 (5)	0.0647 (9)
H9A	0.2529	0.6709	0.6765	0.078*
H9B	0.2762	0.4986	0.7936	0.078*
C10	0.19930 (12)	0.4786 (4)	0.7133 (5)	0.0669 (9)
H10A	0.1754	0.5167	0.5952	0.08*
H10B	0.1988	0.3472	0.7178	0.08*
C11	0.18125 (13)	0.5489 (5)	0.9078 (6)	0.0841 (11)
H11A	0.2054	0.5105	1.0249	0.101*
H11B	0.1823	0.6801	0.9029	0.101*
O2	0.09980 (13)	0.4309 (6)	0.8264 (6)	0.1611 (17)
C12	0.13091 (16)	0.4956 (6)	0.9495 (8)	0.0931 (12)
O3	0.11934 (12)	0.5317 (5)	1.1327 (6)	0.1322 (13)
C13	0.0754 (3)	0.4721 (17)	1.213 (2)	0.154 (4)	0.648 (15)
H13A	0.0548	0.4027	1.1062	0.185*	0.648 (15)
H13B	0.0849	0.3925	1.331	0.185*	0.648 (15)
C14	0.0467 (4)	0.6111 (18)	1.277 (2)	0.149 (4)	0.648 (15)
H14A	0.0674	0.684	1.3768	0.224*	0.648 (15)
H14B	0.0178	0.5636	1.3407	0.224*	0.648 (15)
H14C	0.0345	0.6841	1.1576	0.224*	0.648 (15)
C23	0.0673 (2)	0.508 (4)	1.141 (3)	0.154 (4)	0.352 (15)
H23A	0.0565	0.3919	1.0802	0.185*	0.352 (15)
H23B	0.0481	0.6029	1.0633	0.185*	0.352 (15)
C24	0.0585 (9)	0.514 (4)	1.351 (3)	0.149 (4)	0.352 (15)
H24A	0.0826	0.595	1.425	0.224*	0.352 (15)
H24B	0.0626	0.3946	1.4103	0.224*	0.352 (15)
H24C	0.024	0.5556	1.3618	0.224*	0.352 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0606 (14)	0.0730 (13)	0.0517 (13)	−0.0035 (10)	0.0014 (10)	−0.0074 (10)
C1	0.0582 (18)	0.0454 (14)	0.0449 (17)	0.0036 (12)	0.0020 (13)	0.0044 (12)
C2	0.068 (2)	0.0599 (17)	0.0539 (19)	−0.0092 (15)	0.0088 (15)	−0.0181 (14)
C3	0.066 (2)	0.0552 (16)	0.0546 (18)	−0.0130 (14)	−0.0009 (14)	−0.0180 (14)
C4	0.0593 (16)	0.0314 (12)	0.0371 (14)	0.0003 (11)	−0.0047 (11)	0.0022 (10)
C5	0.0598 (18)	0.0512 (14)	0.0388 (15)	−0.0009 (13)	−0.0034 (12)	−0.0061 (12)
C6	0.0580 (18)	0.0566 (15)	0.0443 (16)	−0.0044 (13)	−0.0083 (13)	−0.0030 (13)
C7	0.0639 (19)	0.0612 (16)	0.055 (2)	0.0043 (14)	0.0003 (15)	−0.0028 (14)
C8	0.0586 (19)	0.0721 (18)	0.061 (2)	0.0001 (14)	0.0015 (15)	−0.0065 (15)
C9	0.0605 (19)	0.0709 (18)	0.061 (2)	0.0058 (15)	−0.0015 (15)	−0.0040 (15)
C10	0.065 (2)	0.0684 (18)	0.066 (2)	0.0011 (15)	−0.0015 (16)	−0.0007 (15)
C11	0.070 (2)	0.103 (3)	0.080 (3)	−0.0058 (19)	0.0096 (19)	−0.014 (2)
O2	0.108 (3)	0.227 (4)	0.151 (3)	−0.068 (3)	0.031 (2)	−0.036 (3)
C12	0.075 (3)	0.103 (3)	0.104 (4)	−0.009 (2)	0.021 (3)	−0.004 (2)
O3	0.107 (2)	0.166 (3)	0.133 (3)	−0.024 (2)	0.063 (2)	−0.017 (2)
C13	0.136 (5)	0.168 (6)	0.171 (7)	−0.013 (4)	0.078 (5)	0.002 (5)
C14	0.116 (6)	0.161 (9)	0.179 (9)	0.005 (6)	0.055 (6)	−0.014 (7)
C23	0.136 (5)	0.168 (6)	0.171 (7)	−0.013 (4)	0.078 (5)	0.002 (5)
C24	0.116 (6)	0.161 (9)	0.179 (9)	0.005 (6)	0.055 (6)	−0.014 (7)

Geometric parameters (Å, º)

O1—C1	1.363 (3)	C10—C11	1.499 (5)
O1—C7	1.421 (3)	C10—H10A	0.99
C1—C6	1.379 (4)	C10—H10B	0.99
C1—C2	1.384 (4)	C11—C12	1.450 (5)
C2—C3	1.375 (4)	C11—H11A	0.99
C2—H2	0.95	C11—H11B	0.99
C3—C4	1.404 (4)	O2—C12	1.197 (5)
C3—H3	0.95	C12—O3	1.294 (5)
C4—C5	1.396 (3)	O3—C23	1.4012 (11)
C4—C4^i	1.460 (5)	O3—C13	1.4021 (11)
C5—C6	1.365 (4)	C13—C14	1.385 (13)
C5—H5	0.95	C13—H13A	0.99
C6—H6	0.95	C13—H13B	0.99
C7—C8	1.504 (4)	C14—H14A	0.98
C7—H7A	0.99	C14—H14B	0.98
C7—H7B	0.99	C14—H14C	0.98
C8—C9	1.506 (4)	C23—C24	1.412 (18)
C8—H8A	0.99	C23—H23A	0.99
C8—H8B	0.99	C23—H23B	0.99
C9—C10	1.519 (4)	C24—H24A	0.98
C9—H9A	0.99	C24—H24B	0.98
C9—H9B	0.99	C24—H24C	0.98
C1—O1—C7	119.0 (2)	C9—C10—H10A	108.8
O1—C1—C6	116.6 (2)	C11—C10—H10B	108.8
O1—C1—C2	125.3 (2)	C9—C10—H10B	108.8
C6—C1—C2	118.0 (3)	H10A—C10—H10B	107.7
C3—C2—C1	120.0 (3)	C12—C11—C10	116.3 (3)
C3—C2—H2	120.0	C12—C11—H11A	108.2
C1—C2—H2	120.0	C10—C11—H11A	108.2
C2—C3—C4	123.4 (3)	C12—C11—H11B	108.2
C2—C3—H3	118.3	C10—C11—H11B	108.2
C4—C3—H3	118.3	H11A—C11—H11B	107.4
C5—C4—C3	114.3 (2)	O2—C12—O3	119.5 (4)
C5—C4—C4^i	123.1 (3)	O2—C12—C11	125.1 (4)
C3—C4—C4^i	122.5 (3)	O3—C12—C11	115.3 (4)
C6—C5—C4	122.9 (3)	C12—O3—C23	109.8 (9)
C6—C5—H5	118.5	C12—O3—C13	124.3 (8)
C4—C5—H5	118.5	C14—C13—O3	112.1 (9)
C5—C6—C1	121.3 (3)	C14—C13—H13A	109.2
C5—C6—H6	119.3	O3—C13—H13A	109.2
C1—C6—H6	119.3	C14—C13—H13B	109.2
O1—C7—C8	107.6 (2)	O3—C13—H13B	109.2
O1—C7—H7A	110.2	H13A—C13—H13B	107.9
C8—C7—H7A	110.2	C13—C14—H14A	109.5
O1—C7—H7B	110.2	C13—C14—H14B	109.5
C8—C7—H7B	110.2	H14A—C14—H14B	109.5
H7A—C7—H7B	108.5	C13—C14—H14C	109.5
C7—C8—C9	113.8 (3)	H14A—C14—H14C	109.5
C7—C8—H8A	108.8	H14B—C14—H14C	109.5
C9—C8—H8A	108.8	O3—C23—C24	107.3 (15)
C7—C8—H8B	108.8	O3—C23—H23A	110.3
C9—C8—H8B	108.8	C24—C23—H23A	110.3
H8A—C8—H8B	107.7	O3—C23—H23B	110.3
C8—C9—C10	113.4 (3)	C24—C23—H23B	110.2
C8—C9—H9A	108.9	H23A—C23—H23B	108.5
C10—C9—H9A	108.9	C23—C24—H24A	109.5
C8—C9—H9B	108.9	C23—C24—H24B	109.5
C10—C9—H9B	108.9	H24A—C24—H24B	109.5
H9A—C9—H9B	107.7	C23—C24—H24C	109.5
C11—C10—C9	113.9 (3)	H24A—C24—H24C	109.5
C11—C10—H10A	108.8	H24B—C24—H24C	109.5
C7—O1—C1—C6	171.6 (2)	O1—C7—C8—C9	−175.7 (2)
C7—O1—C1—C2	−7.1 (4)	C7—C8—C9—C10	177.7 (2)
O1—C1—C2—C3	177.6 (3)	C8—C9—C10—C11	−178.5 (3)
C6—C1—C2—C3	−1.1 (4)	C9—C10—C11—C12	179.7 (3)
C1—C2—C3—C4	0.5 (5)	C10—C11—C12—O2	−15.2 (7)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12—O3	168.7 (3)
C2—C3—C4—C4^i	−179.4 (3)	O2—C12—O3—C23	−8.4 (16)
C3—C4—C5—C6	−0.5 (4)	C11—C12—O3—C23	168.0 (15)
C4^i—C4—C5—C6	179.2 (3)	O2—C12—O3—C13	12.0 (10)
C4—C5—C6—C1	−0.1 (4)	C11—C12—O3—C13	−171.6 (8)
O1—C1—C6—C5	−177.9 (2)	C12—O3—C13—C14	−122.9 (14)
C2—C1—C6—C5	0.9 (4)	C12—O3—C23—C24	168 (2)
C1—O1—C7—C8	−169.2 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

Cg refers to the centroid of the symmetry-unique phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2^ii	0.99	2.47	3.177 (13)	128
C6—H6···O1^iii	0.95	2.78	3.601 (3)	145
C5—H5···Cg^iii	0.95	2.92	3.716 (3)	142
C2—H2···Cg^iv	0.95	3.02	3.799 (3)	141

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