Influence of 1,4-dioxane solvent inclusion on the crystal structure of 5,5'-diphenyl-2,2'-(p-phenyl­ene)di-1,3-oxazole (POPOP)

Crystallization of 5,5'-diphenyl-2,2'-(p-phenyl­ene)di-1,3-ox­az­ole (POPOP), C₂₄H₁₆N₂O₂, from chloro­form or 1,4-di­oxane yielded crystals in pure and solvated forms, respectively. The solvated crystals of POPOP were found to contain 1,4-dioxane in a strict 1:2 compound-solvent stoichiometry, C₂₄H₁₆N₂O₂·C₄H₈O₂, thus being a defined solvent-inclusion compound. The crystal system is monoclinic in both cases and the asymmetric unit of the cell contains only half of the mol­ecule (plus one dioxane mol­ecule in the case of the solvated structure), owing to the centrosymmetry of the di-1,3-oxazole mol­ecule.

Computing details

For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) 5,5'-diphenyl-2,2'-(p-phenylene)di-1,3-oxazole

Crystal data

C24H16N2O2	F(000) = 380
Mr = 364.39	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Melting point = 517–519 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.1393 (14) Å	Cell parameters from 2741 reflections
b = 5.2461 (8) Å	θ = 2.2–29.2°
c = 19.204 (3) Å	µ = 0.09 mm^−1
β = 91.807 (11)°	T = 153 K
V = 920.3 (3) Å^3	Plate, colourless
Z = 2	0.27 × 0.14 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2107 independent reflections
Radiation source: fine-focus sealed tube	1644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.978, Tmax = 0.991	k = −6→6
16533 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.2332P] where P = (Fo^2 + 2Fc^2)/3
2107 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.38668 (13)	0.8295 (2)	−0.01505 (6)	0.0247 (3)
H1	0.3091	0.7135	−0.0253	0.030*
C2	0.57922 (13)	0.9840 (2)	0.06280 (6)	0.0248 (3)
H2	0.6331	0.9733	0.1058	0.030*
C3	0.46596 (13)	0.8113 (2)	0.04816 (6)	0.0222 (3)
C4	0.43224 (13)	0.6177 (2)	0.09976 (6)	0.0224 (3)
C5	0.42273 (14)	0.3743 (2)	0.18784 (6)	0.0261 (3)
H5	0.4451	0.2979	0.2318	0.031*
C6	0.31054 (13)	0.3051 (2)	0.14422 (6)	0.0234 (3)
C7	0.19573 (13)	0.1136 (2)	0.14648 (6)	0.0237 (3)
C8	0.08296 (15)	0.1035 (3)	0.09601 (7)	0.0306 (3)
H8	0.0797	0.2243	0.0591	0.037*
C9	−0.02462 (15)	−0.0822 (3)	0.09940 (7)	0.0362 (3)
H9	−0.1007	−0.0888	0.0646	0.043*
C10	−0.02188 (15)	−0.2579 (3)	0.15314 (8)	0.0352 (3)
H10	−0.0961	−0.3841	0.1554	0.042*
C11	0.08988 (15)	−0.2491 (2)	0.20384 (7)	0.0318 (3)
H11	0.0920	−0.3694	0.2408	0.038*
C12	0.19801 (14)	−0.0655 (2)	0.20057 (7)	0.0267 (3)
H12	0.2744	−0.0609	0.2353	0.032*
Cg1	0.0867	−0.0729	0.1499	0.010*	0.00
Cg2	0.3962	0.4663	0.1355	0.010*	0.00
N1	0.50023 (12)	0.57309 (19)	0.15899 (5)	0.0258 (2)
O1	0.31544 (9)	0.46141 (16)	0.08657 (4)	0.0234 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0252 (6)	0.0238 (6)	0.0250 (6)	−0.0009 (5)	0.0003 (5)	−0.0011 (5)
C2	0.0262 (6)	0.0262 (6)	0.0219 (6)	0.0025 (5)	−0.0013 (5)	0.0001 (5)
C3	0.0246 (6)	0.0217 (6)	0.0206 (6)	0.0039 (5)	0.0036 (5)	−0.0007 (5)
C4	0.0242 (6)	0.0212 (6)	0.0219 (6)	0.0009 (5)	0.0015 (5)	−0.0027 (5)
C5	0.0327 (7)	0.0228 (6)	0.0227 (6)	0.0009 (5)	0.0008 (5)	0.0026 (5)
C6	0.0286 (6)	0.0214 (6)	0.0204 (6)	0.0045 (5)	0.0041 (5)	0.0015 (5)
C7	0.0252 (6)	0.0225 (6)	0.0236 (6)	0.0032 (5)	0.0047 (5)	−0.0020 (5)
C8	0.0333 (7)	0.0320 (7)	0.0265 (7)	−0.0010 (6)	0.0007 (5)	0.0027 (5)
C9	0.0315 (7)	0.0419 (8)	0.0351 (8)	−0.0044 (6)	−0.0002 (6)	−0.0071 (6)
C10	0.0333 (7)	0.0305 (7)	0.0424 (8)	−0.0064 (6)	0.0104 (6)	−0.0065 (6)
C11	0.0347 (7)	0.0248 (7)	0.0364 (7)	0.0026 (5)	0.0117 (6)	0.0034 (5)
C12	0.0271 (6)	0.0256 (7)	0.0275 (6)	0.0042 (5)	0.0047 (5)	0.0012 (5)
N1	0.0307 (6)	0.0242 (5)	0.0224 (5)	−0.0001 (4)	−0.0004 (4)	0.0013 (4)
O1	0.0260 (4)	0.0235 (4)	0.0209 (4)	−0.0011 (3)	0.0007 (3)	0.0024 (3)

Geometric parameters (Å, º)

C1—C2^i	1.3832 (17)	C6—C7	1.4544 (17)
C1—C3	1.3970 (17)	C7—C8	1.3934 (18)
C1—H1	0.9500	C7—C12	1.4002 (17)
C2—C1^i	1.3832 (17)	C8—C9	1.3871 (19)
C2—C3	1.3977 (17)	C8—H8	0.9500
C2—H2	0.9500	C9—C10	1.383 (2)
C3—C4	1.4584 (17)	C9—H9	0.9500
C4—N1	1.3001 (15)	C10—C11	1.390 (2)
C4—O1	1.3635 (14)	C10—H10	0.9500
C5—C6	1.3530 (17)	C11—C12	1.3825 (18)
C5—N1	1.3859 (16)	C11—H11	0.9500
C5—H5	0.9500	C12—H12	0.9500
C6—O1	1.3797 (14)
C2^i—C1—C3	120.19 (11)	C8—C7—C6	121.60 (11)
C2^i—C1—H1	119.9	C12—C7—C6	119.46 (11)
C3—C1—H1	119.9	C9—C8—C7	120.26 (12)
C1^i—C2—C3	120.41 (11)	C9—C8—H8	119.9
C1^i—C2—H2	119.8	C7—C8—H8	119.9
C3—C2—H2	119.8	C10—C9—C8	120.45 (13)
C1—C3—C2	119.40 (11)	C10—C9—H9	119.8
C1—C3—C4	121.54 (11)	C8—C9—H9	119.8
C2—C3—C4	119.06 (11)	C9—C10—C11	119.74 (13)
N1—C4—O1	113.83 (10)	C9—C10—H10	120.1
N1—C4—C3	127.92 (11)	C11—C10—H10	120.1
O1—C4—C3	118.26 (10)	C12—C11—C10	120.14 (13)
C6—C5—N1	109.96 (11)	C12—C11—H11	119.9
C6—C5—H5	125.0	C10—C11—H11	119.9
N1—C5—H5	125.0	C11—C12—C7	120.47 (12)
C5—C6—O1	107.11 (11)	C11—C12—H12	119.8
C5—C6—C7	134.45 (11)	C7—C12—H12	119.8
O1—C6—C7	118.44 (10)	C4—N1—C5	104.43 (10)
C8—C7—C12	118.94 (12)	C4—O1—C6	104.68 (9)
C2^i—C1—C3—C2	0.4 (2)	C6—C7—C8—C9	179.70 (12)
C2^i—C1—C3—C4	179.67 (11)	C7—C8—C9—C10	0.5 (2)
C1^i—C2—C3—C1	−0.4 (2)	C8—C9—C10—C11	−0.3 (2)
C1^i—C2—C3—C4	−179.69 (11)	C9—C10—C11—C12	−0.1 (2)
C1—C3—C4—N1	177.04 (12)	C10—C11—C12—C7	0.28 (19)
C2—C3—C4—N1	−3.70 (19)	C8—C7—C12—C11	−0.10 (19)
C1—C3—C4—O1	−3.43 (17)	C6—C7—C12—C11	179.89 (11)
C2—C3—C4—O1	175.83 (10)	O1—C4—N1—C5	−0.56 (14)
N1—C5—C6—O1	−0.13 (14)	C3—C4—N1—C5	178.99 (12)
N1—C5—C6—C7	179.87 (12)	C6—C5—N1—C4	0.41 (14)
C5—C6—C7—C8	172.92 (14)	N1—C4—O1—C6	0.50 (13)
O1—C6—C7—C8	−7.09 (17)	C3—C4—O1—C6	−179.10 (10)
C5—C6—C7—C12	−7.1 (2)	C5—C6—O1—C4	−0.20 (12)
O1—C6—C7—C12	172.92 (10)	C7—C6—O1—C4	179.80 (10)
C12—C7—C8—C9	−0.31 (19)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1^ii	0.95	2.44	3.3932 (16)	176
C11—H11···Cg1^iii	0.95	2.90	3.6966 (14)	142

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

(II) 5,5'-diphenyl-2,2'-(p-phenylene)di-1,3-oxazole dioxane disolvate

Crystal data

C24H16N2O2·2C4H8O2	F(000) = 572
Mr = 540.60	Dx = 1.354 Mg m^−3
Monoclinic, P21/n	Melting point = 519–519 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.2424 (6) Å	Cell parameters from 4956 reflections
b = 5.9115 (3) Å	θ = 3.4–32.3°
c = 18.5046 (9) Å	µ = 0.09 mm^−1
β = 97.977 (3)°	T = 153 K
V = 1326.24 (11) Å^3	Needle, colourless
Z = 2	0.44 × 0.11 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1857 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.960, Tmax = 0.992	k = −6→7
22800 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.4537P] where P = (Fo^2 + 2Fc^2)/3
2324 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.40678 (10)	0.1364 (2)	−0.01121 (7)	0.0227 (3)
H1	0.3429	0.2293	−0.0189	0.027*
C2	0.58498 (10)	0.0496 (2)	0.05524 (7)	0.0230 (3)
H2	0.6432	0.0834	0.0932	0.028*
C3	0.49169 (10)	0.1887 (2)	0.04453 (7)	0.0211 (3)
C4	0.48480 (10)	0.3818 (2)	0.09274 (7)	0.0211 (3)
C5	0.50790 (11)	0.6286 (2)	0.17666 (7)	0.0257 (3)
H5	0.5396	0.7111	0.2184	0.031*
C6	0.41094 (10)	0.6784 (2)	0.13583 (7)	0.0212 (3)
C7	0.32829 (10)	0.8534 (2)	0.13969 (7)	0.0222 (3)
C8	0.22431 (11)	0.8439 (2)	0.09840 (7)	0.0279 (3)
H8	0.2060	0.7220	0.0655	0.033*
C9	0.14739 (12)	1.0118 (3)	0.10520 (8)	0.0328 (3)
H9	0.0766	1.0044	0.0768	0.039*
C10	0.17278 (12)	1.1902 (2)	0.15296 (8)	0.0319 (3)
H10	0.1194	1.3037	0.1578	0.038*
C11	0.27666 (11)	1.2024 (2)	0.19378 (7)	0.0288 (3)
H11	0.2948	1.3253	0.2263	0.035*
C12	0.35364 (11)	1.0356 (2)	0.18707 (7)	0.0248 (3)
H12	0.4247	1.0450	0.2150	0.030*
N1	0.55444 (9)	0.44003 (19)	0.14900 (6)	0.0255 (3)
O1	0.39440 (7)	0.51870 (15)	0.08077 (5)	0.0215 (2)
C13	0.61584 (12)	1.3224 (2)	0.33040 (8)	0.0315 (3)
H13A	0.6465	1.4635	0.3126	0.038*
H13B	0.5354	1.3212	0.3138	0.038*
C14	0.66792 (12)	1.1228 (3)	0.29878 (8)	0.0344 (4)
H14A	0.6516	1.1274	0.2449	0.041*
H14B	0.7490	1.1296	0.3124	0.041*
C15	0.64950 (13)	0.9120 (3)	0.40270 (8)	0.0355 (4)
H15A	0.7302	0.9159	0.4181	0.043*
H15B	0.6206	0.7701	0.4212	0.043*
C16	0.59690 (13)	1.1111 (2)	0.43462 (8)	0.0338 (3)
H16A	0.5158	1.1018	0.4216	0.041*
H16B	0.6141	1.1065	0.4885	0.041*
O2	0.63519 (8)	1.31862 (16)	0.40845 (5)	0.0326 (3)
O3	0.62697 (9)	0.91601 (17)	0.32503 (5)	0.0379 (3)
CG1	0.2505	1.0229	0.1462	0.010*	0.00
CG2	0.4705	0.5295	0.1270	0.010*	0.00
CG3	0.5000	0.0000	0.0000	0.010*	0.00

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0224 (6)	0.0219 (7)	0.0242 (7)	0.0029 (5)	0.0049 (5)	0.0037 (5)
C2	0.0227 (6)	0.0236 (7)	0.0226 (7)	−0.0011 (5)	0.0027 (5)	0.0017 (5)
C3	0.0252 (6)	0.0191 (7)	0.0204 (6)	−0.0020 (5)	0.0077 (5)	0.0035 (5)
C4	0.0210 (6)	0.0194 (7)	0.0236 (6)	0.0000 (5)	0.0058 (5)	0.0044 (5)
C5	0.0296 (7)	0.0226 (7)	0.0248 (7)	−0.0010 (6)	0.0033 (6)	−0.0033 (6)
C6	0.0271 (7)	0.0177 (7)	0.0197 (6)	−0.0026 (5)	0.0063 (5)	−0.0008 (5)
C7	0.0269 (7)	0.0197 (7)	0.0216 (6)	−0.0021 (5)	0.0090 (5)	0.0034 (5)
C8	0.0312 (7)	0.0254 (8)	0.0271 (7)	0.0001 (6)	0.0043 (6)	−0.0025 (6)
C9	0.0291 (7)	0.0323 (8)	0.0367 (8)	0.0044 (6)	0.0031 (6)	0.0035 (7)
C10	0.0347 (8)	0.0250 (8)	0.0383 (8)	0.0077 (6)	0.0134 (7)	0.0045 (6)
C11	0.0384 (8)	0.0203 (7)	0.0306 (8)	−0.0028 (6)	0.0145 (6)	−0.0016 (6)
C12	0.0269 (7)	0.0238 (7)	0.0249 (7)	−0.0040 (6)	0.0084 (5)	0.0007 (6)
N1	0.0264 (6)	0.0225 (6)	0.0270 (6)	0.0007 (5)	0.0019 (5)	−0.0011 (5)
O1	0.0236 (4)	0.0192 (5)	0.0223 (5)	0.0019 (4)	0.0047 (4)	−0.0013 (4)
C13	0.0343 (8)	0.0279 (8)	0.0312 (8)	−0.0002 (6)	0.0008 (6)	0.0048 (6)
C14	0.0354 (8)	0.0359 (9)	0.0315 (8)	0.0026 (7)	0.0041 (6)	0.0031 (7)
C15	0.0481 (9)	0.0240 (8)	0.0325 (8)	−0.0009 (7)	−0.0009 (7)	0.0016 (6)
C16	0.0416 (8)	0.0283 (8)	0.0308 (8)	−0.0019 (6)	0.0030 (6)	0.0027 (6)
O2	0.0420 (6)	0.0222 (5)	0.0318 (5)	−0.0016 (4)	−0.0015 (4)	−0.0019 (4)
O3	0.0533 (7)	0.0266 (6)	0.0321 (6)	−0.0018 (5)	−0.0006 (5)	−0.0045 (5)

Geometric parameters (Å, º)

C1—C2^i	1.3805 (19)	C10—H10	0.9500
C1—C3	1.3936 (18)	C11—C12	1.3813 (19)
C1—H1	0.9500	C11—H11	0.9500
C2—C1^i	1.3805 (19)	C12—H12	0.9500
C2—C3	1.3990 (18)	C13—O2	1.4310 (17)
C2—H2	0.9500	C13—C14	1.498 (2)
C3—C4	1.4587 (18)	C13—H13A	0.9900
C4—N1	1.2971 (16)	C13—H13B	0.9900
C4—O1	1.3641 (15)	C14—O3	1.4314 (18)
C5—C6	1.3482 (18)	C14—H14A	0.9900
C5—N1	1.3820 (17)	C14—H14B	0.9900
C5—H5	0.9500	C15—O3	1.4257 (17)
C6—O1	1.3830 (15)	C15—C16	1.501 (2)
C6—C7	1.4557 (18)	C15—H15A	0.9900
C7—C8	1.3919 (18)	C15—H15B	0.9900
C7—C12	1.3963 (19)	C16—O2	1.4221 (17)
C8—C9	1.386 (2)	C16—H16A	0.9900
C8—H8	0.9500	C16—H16B	0.9900
C9—C10	1.383 (2)	CG3—C2^i	1.3849 (13)
C9—H9	0.9500	CG3—C1^i	1.3894 (13)
C10—C11	1.388 (2)
C2^i—C1—C3	120.34 (12)	C11—C12—C7	120.81 (13)
C2^i—C1—H1	119.8	C11—C12—H12	119.6
C3—C1—H1	119.8	C7—C12—H12	119.6
C1^i—C2—C3	120.64 (12)	C4—N1—C5	104.62 (11)
C1^i—C2—H2	119.7	C4—O1—C6	104.63 (10)
C3—C2—H2	119.7	O2—C13—C14	111.22 (11)
C1—C3—C2	119.02 (12)	O2—C13—H13A	109.4
C1—C3—C4	121.71 (11)	C14—C13—H13A	109.4
C2—C3—C4	119.26 (11)	O2—C13—H13B	109.4
N1—C4—O1	113.64 (11)	C14—C13—H13B	109.4
N1—C4—C3	127.68 (12)	H13A—C13—H13B	108.0
O1—C4—C3	118.65 (11)	O3—C14—C13	110.61 (11)
C6—C5—N1	110.16 (11)	O3—C14—H14A	109.5
C6—C5—H5	124.9	C13—C14—H14A	109.5
N1—C5—H5	124.9	O3—C14—H14B	109.5
C5—C6—O1	106.94 (11)	C13—C14—H14B	109.5
C5—C6—C7	133.75 (12)	H14A—C14—H14B	108.1
O1—C6—C7	119.30 (11)	O3—C15—C16	110.49 (12)
C8—C7—C12	118.84 (12)	O3—C15—H15A	109.6
C8—C7—C6	122.23 (12)	C16—C15—H15A	109.6
C12—C7—C6	118.93 (12)	O3—C15—H15B	109.6
C9—C8—C7	120.16 (13)	C16—C15—H15B	109.6
C9—C8—H8	119.9	H15A—C15—H15B	108.1
C7—C8—H8	119.9	O2—C16—C15	111.27 (12)
C10—C9—C8	120.58 (13)	O2—C16—H16A	109.4
C10—C9—H9	119.7	C15—C16—H16A	109.4
C8—C9—H9	119.7	O2—C16—H16B	109.4
C9—C10—C11	119.67 (13)	C15—C16—H16B	109.4
C9—C10—H10	120.2	H16A—C16—H16B	108.0
C11—C10—H10	120.2	C16—O2—C13	109.93 (10)
C12—C11—C10	119.93 (13)	C15—O3—C14	109.17 (11)
C12—C11—H11	120.0	C2^i—CG3—C1^i	120.32 (8)
C10—C11—H11	120.0
C2^i—C1—C3—C2	−0.2 (2)	C9—C10—C11—C12	−0.7 (2)
C2^i—C1—C3—C4	−179.00 (11)	C10—C11—C12—C7	−0.2 (2)
C1^i—C2—C3—C1	0.2 (2)	C8—C7—C12—C11	0.87 (19)
C1^i—C2—C3—C4	179.03 (11)	C6—C7—C12—C11	−178.36 (12)
C1—C3—C4—N1	175.38 (13)	O1—C4—N1—C5	−0.05 (14)
C2—C3—C4—N1	−3.4 (2)	C3—C4—N1—C5	−178.03 (12)
C1—C3—C4—O1	−2.51 (18)	C6—C5—N1—C4	−0.03 (14)
C2—C3—C4—O1	178.69 (11)	N1—C4—O1—C6	0.10 (14)
N1—C5—C6—O1	0.09 (14)	C3—C4—O1—C6	178.28 (10)
N1—C5—C6—C7	179.60 (13)	C5—C6—O1—C4	−0.11 (13)
C5—C6—C7—C8	−167.72 (14)	C7—C6—O1—C4	−179.71 (11)
O1—C6—C7—C8	11.75 (18)	O2—C13—C14—O3	57.68 (15)
C5—C6—C7—C12	11.5 (2)	O3—C15—C16—O2	−58.38 (16)
O1—C6—C7—C12	−169.05 (11)	C15—C16—O2—C13	56.11 (15)
C12—C7—C8—C9	−0.7 (2)	C14—C13—O2—C16	−55.87 (15)
C6—C7—C8—C9	178.46 (12)	C16—C15—O3—C14	58.57 (15)
C7—C8—C9—C10	−0.1 (2)	C13—C14—O3—C15	−58.42 (15)
C8—C9—C10—C11	0.8 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···N1^ii	0.99	2.72	3.4728 (18)	133
C5—H5···O3	0.95	2.43	3.3821 (16)	178
C15—H15B···O2^iii	0.99	2.69	3.5146 (18)	141
C14—H14B···N1^iv	0.99	2.66	3.5697 (18)	153
C13—H13A···O3^ii	0.99	2.70	3.5138 (18)	140

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