Methyl 3,4-bis-(cyclo-propyl-meth-oxy)benzoate.

The title compound, C(16)H(20)O(4), was obtained unintentionally as the byproduct of an attempted synthesis of methyl 3-(cyclo-propyl-meth-oxy)-4-hy-droxy-benzoate. In the crystal, the mol-ecules are linked by inter-molecular C-H⋯O inter-actions.

Related literature

For the preparation, see: Bose et al. (2005 ▶). For a similar structure, see: Hou et al. (2010 ▶).

Experimental

Crystal data

C16H20O4

M = 276.33

Orthorhombic,

a = 4.9018 (8) Å

b = 15.543 (2) Å

c = 18.846 (2) Å

V = 1435.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.891, T max = 0.984

20068 measured reflections

3852 independent reflections

3300 reflections with F 2 > 2.0σ(F 2)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.06

3852 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013158/jh2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013158/jh2279Isup2.hkl

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

C16H20O4	F(000) = 592.00
Mr = 276.33	Dx = 1.278 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6064 reflections
a = 4.9018 (8) Å	θ = 1.3–31.4°
b = 15.543 (2) Å	µ = 0.09 mm−1
c = 18.846 (2) Å	T = 113 K
V = 1435.9 (3) Å3	Prism, colorless
Z = 4	0.22 × 0.20 × 0.18 mm

Rigaku Saturn724 CCD diffractometer	3300 reflections with F2 > 2.0σ(F2)
Detector resolution: 14.222 pixels mm-1	Rint = 0.034
ω scans	θmax = 29.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −6→6
Tmin = 0.891, Tmax = 0.984	k = −21→21
20068 measured reflections	l = −25→25
3852 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3
3852 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O(1)	0.3872 (2)	0.69719 (7)	0.66936 (5)	0.0321
O(2)	0.6968 (2)	0.59026 (7)	0.66908 (5)	0.0306
O(3)	0.7825 (2)	0.48335 (5)	0.42141 (5)	0.0209
O(4)	0.4320 (2)	0.56811 (6)	0.34625 (4)	0.0250
C(1)	0.4862 (3)	0.62225 (8)	0.56094 (7)	0.0192
C(2)	0.6558 (3)	0.56094 (8)	0.52884 (7)	0.0184
C(3)	0.6319 (3)	0.54351 (8)	0.45719 (6)	0.0174
C(4)	0.4378 (3)	0.58918 (8)	0.41612 (7)	0.0193
C(5)	0.2695 (3)	0.64967 (8)	0.44863 (7)	0.0213
C(6)	0.2930 (3)	0.66574 (8)	0.52102 (7)	0.0211
C(7)	0.5139 (3)	0.64194 (8)	0.63788 (7)	0.0216
C(8)	0.7487 (4)	0.60502 (11)	0.74361 (7)	0.0406
C(9)	0.9395 (3)	0.42507 (8)	0.46452 (6)	0.0199
C(10)	1.0118 (3)	0.34763 (8)	0.42075 (7)	0.0205
C(11)	1.2662 (3)	0.29938 (9)	0.44212 (8)	0.0262
C(12)	1.2614 (3)	0.35005 (9)	0.37423 (7)	0.0246
C(13)	0.2283 (3)	0.61039 (9)	0.30217 (7)	0.0302
C(14)	0.2718 (4)	0.57919 (10)	0.22787 (7)	0.0330
C(15)	0.5052 (4)	0.61632 (12)	0.18752 (10)	0.0442
C(16)	0.2225 (4)	0.64137 (13)	0.16830 (8)	0.0428
H(2)	0.7878	0.5312	0.5565	0.022*
H(5)	0.1381	0.6800	0.4213	0.026*
H(6)	0.1765	0.7066	0.5431	0.025*
H(8A)	0.5750	0.6078	0.7693	0.049*
H(8B)	0.8469	0.6595	0.7495	0.049*
H(8C)	0.8593	0.5578	0.7626	0.049*
H(9A)	0.8319	0.4073	0.5065	0.024*
H(9B)	1.1078	0.4538	0.4813	0.024*
H(10)	0.8558	0.3120	0.4033	0.025*
H(11A)	1.3747	0.3225	0.4821	0.031*
H(11B)	1.2633	0.2358	0.4386	0.031*
H(12A)	1.2558	0.3176	0.3291	0.030*
H(12B)	1.3671	0.4043	0.3725	0.030*
H(13A)	0.2504	0.6736	0.3045	0.036*
H(13B)	0.0423	0.5955	0.3186	0.036*
H(14)	0.2271	0.5175	0.2183	0.040*
H(15A)	0.6201	0.6597	0.2118	0.053*
H(15B)	0.6047	0.5779	0.1546	0.053*
H(16A)	0.1462	0.6184	0.1235	0.051*
H(16B)	0.1615	0.7002	0.1807	0.051*

	U11	U22	U33	U12	U13	U23
O(1)	0.0398	0.0311	0.0253	0.0080	0.0001	−0.0084
O(2)	0.0391	0.0348	0.0179	0.0103	−0.0046	−0.0070
O(3)	0.0251	0.0207	0.0170	0.0073	−0.0011	0.0001
O(4)	0.0346	0.0232	0.0170	0.0084	−0.0041	0.0008
C(1)	0.0205	0.0176	0.0194	−0.0020	0.0025	−0.0008
C(2)	0.0171	0.0187	0.0194	−0.0004	−0.0002	−0.0003
C(3)	0.0192	0.0152	0.0178	0.0006	0.0017	−0.0000
C(4)	0.0228	0.0182	0.0170	−0.0013	−0.0017	0.0020
C(5)	0.0222	0.0188	0.0229	0.0010	−0.0014	0.0024
C(6)	0.0213	0.0185	0.0235	0.0012	0.0042	−0.0012
C(7)	0.0243	0.0197	0.0208	−0.0031	0.0009	−0.0025
C(8)	0.0575	0.0441	0.0202	0.0155	−0.0122	−0.0113
C(9)	0.0213	0.0205	0.0179	0.0038	−0.0004	0.0030
C(10)	0.0189	0.0203	0.0222	0.0011	0.0009	0.0013
C(11)	0.0251	0.0244	0.0291	0.0071	0.0026	0.0046
C(12)	0.0247	0.0255	0.0236	0.0017	0.0060	0.0002
C(13)	0.0337	0.0335	0.0235	0.0069	−0.0052	0.0038
C(14)	0.0389	0.0350	0.0251	0.0013	−0.0049	0.0053
C(15)	0.0457	0.0498	0.0371	0.0028	0.0038	0.0098
C(16)	0.0510	0.0542	0.0230	0.0148	−0.0043	0.0114

O(1)—C(7)	1.2143 (17)	C(15)—C(16)	1.484 (3)
O(2)—C(7)	1.3397 (11)	C(2)—H(2)	0.950
O(2)—C(8)	1.4458 (19)	C(5)—H(5)	0.950
O(3)—C(3)	1.3692 (14)	C(6)—H(6)	0.950
O(3)—C(9)	1.4397 (10)	C(8)—H(8A)	0.980
O(4)—C(4)	1.3572 (17)	C(8)—H(8B)	0.980
O(4)—C(13)	1.4558 (13)	C(8)—H(8C)	0.980
C(1)—C(2)	1.4017 (18)	C(9)—H(9A)	0.990
C(1)—C(6)	1.3856 (15)	C(9)—H(9B)	0.990
C(1)—C(7)	1.488 (3)	C(10)—H(10)	1.000
C(2)—C(3)	1.382 (3)	C(11)—H(11A)	0.990
C(3)—C(4)	1.4169 (14)	C(11)—H(11B)	0.990
C(4)—C(5)	1.3930 (18)	C(12)—H(12A)	0.990
C(5)—C(6)	1.392 (3)	C(12)—H(12B)	0.990
C(9)—C(10)	1.502 (2)	C(13)—H(13A)	0.990
C(10)—C(11)	1.5098 (14)	C(13)—H(13B)	0.990
C(10)—C(12)	1.506 (2)	C(14)—H(14)	1.000
C(11)—C(12)	1.5026 (17)	C(15)—H(15A)	0.990
C(13)—C(14)	1.497 (3)	C(15)—H(15B)	0.990
C(14)—C(15)	1.490 (3)	C(16)—H(16A)	0.990
C(14)—C(16)	1.5009 (15)	C(16)—H(16B)	0.990
O(1)···C(6)	2.875 (2)	H(6)···C(1)viii	3.4340
O(1)···C(8)	2.6738 (14)	H(6)···C(2)iv	3.4221
O(2)···C(2)	2.6895 (19)	H(6)···C(4)viii	3.4694
O(3)···O(4)	2.5873 (12)	H(6)···C(5)viii	2.9995
O(3)···C(12)	3.2546 (14)	H(6)···C(6)viii	2.9886
O(4)···C(15)	3.1046 (16)	H(6)···H(2)iv	3.3350
C(1)···C(4)	2.787 (3)	H(6)···H(5)viii	3.2433
C(2)···C(5)	2.7880 (15)	H(6)···H(5)i	2.9456
C(2)···C(9)	2.804 (2)	H(6)···H(6)viii	3.2354
C(3)···C(6)	2.7955 (18)	H(6)···H(6)i	3.2354
C(5)···C(13)	2.834 (3)	H(8A)···O(3)ii	3.2735
O(1)···C(13)i	3.468 (4)	H(8A)···C(10)ii	2.9685
O(2)···C(15)ii	3.545 (2)	H(8A)···C(12)ii	2.6574
O(3)···C(5)iii	3.556 (2)	H(8A)···C(14)ix	3.4558
O(3)···C(12)iv	3.407 (2)	H(8A)···H(8C)iv	3.5954
O(4)···C(12)iv	3.5306 (19)	H(8A)···H(10)ii	2.8381
C(2)···C(6)iii	3.526 (3)	H(8A)···H(12A)ii	2.2901
C(3)···C(5)iii	3.538 (3)	H(8A)···H(12B)ii	2.9188
C(5)···O(3)iv	3.556 (3)	H(8A)···H(12B)v	3.3617
C(5)···C(3)iv	3.538 (3)	H(8A)···H(13B)ix	3.3436
C(6)···C(2)iv	3.526 (3)	H(8A)···H(14)ix	2.6278
C(8)···C(12)ii	3.578 (3)	H(8A)···H(16B)i	3.1585
C(8)···C(12)v	3.509 (7)	H(8B)···O(1)iii	3.1047
C(12)···O(3)iii	3.407 (4)	H(8B)···C(12)v	3.0389
C(12)···O(4)iii	3.531 (3)	H(8B)···C(16)i	3.5151
C(12)···C(8)vi	3.578 (5)	H(8B)···H(10)ii	3.0967
C(12)···C(8)vii	3.509 (5)	H(8B)···H(12A)ii	3.3323
C(13)···O(1)viii	3.468 (3)	H(8B)···H(12A)v	2.4836
C(15)···O(2)vi	3.545 (3)	H(8B)···H(12B)v	2.8849
C(15)···C(16)iii	3.556 (4)	H(8B)···H(13A)i	2.8266
C(16)···C(15)iv	3.556 (3)	H(8B)···H(14)ii	3.5027
O(1)···H(6)	2.5982	H(8B)···H(15A)i	3.1979
O(1)···H(8A)	2.5145	H(8B)···H(16B)i	2.7043
O(1)···H(8B)	2.7752	H(8C)···O(3)ii	3.1385
O(2)···H(2)	2.3550	H(8C)···O(4)ii	2.7133
O(3)···H(2)	2.6517	H(8C)···C(12)v	3.1519
O(3)···H(10)	2.7092	H(8C)···C(13)ii	3.3878
O(3)···H(12B)	3.2512	H(8C)···C(14)ii	2.8694
O(4)···H(5)	2.6652	H(8C)···C(15)ii	3.1254
O(4)···H(14)	2.7276	H(8C)···H(8A)iii	3.5954
O(4)···H(15A)	3.0496	H(8C)···H(10)ii	3.4987
C(1)···H(5)	3.2624	H(8C)···H(12A)v	2.9798
C(2)···H(6)	3.2736	H(8C)···H(12B)v	2.5373
C(2)···H(9A)	2.5735	H(8C)···H(13B)ix	3.2663
C(2)···H(9B)	2.9122	H(8C)···H(14)ix	3.2138
C(3)···H(5)	3.2890	H(8C)···H(14)ii	2.4852
C(3)···H(9A)	2.5109	H(8C)···H(15A)ii	3.5154
C(3)···H(9B)	2.7551	H(8C)···H(15B)ii	2.9371
C(4)···H(2)	3.2784	H(9A)···C(11)iv	3.4606
C(4)···H(6)	3.2707	H(9A)···C(11)x	3.3711
C(4)···H(13A)	2.6440	H(9A)···C(15)ii	3.5231
C(4)···H(13B)	2.6731	H(9A)···H(11A)iv	2.6402
C(5)···H(13A)	2.7429	H(9A)···H(11A)x	3.5855
C(5)···H(13B)	2.8201	H(9A)···H(11B)x	2.4769
C(6)···H(2)	3.2707	H(9A)···H(12B)iv	3.4008
C(7)···H(2)	2.6681	H(9A)···H(15B)ii	2.8173
C(7)···H(6)	2.6334	H(9A)···H(16A)ix	3.2426
C(7)···H(8A)	2.5499	H(9A)···H(16A)ii	3.4014
C(7)···H(8B)	2.6766	H(9B)···O(3)iii	3.5250
C(7)···H(8C)	3.1783	H(9B)···O(4)iii	3.4870
C(9)···H(2)	2.5055	H(9B)···C(1)iii	3.5419
C(9)···H(11A)	2.6830	H(9B)···C(2)iii	3.2847
C(9)···H(11B)	3.3775	H(9B)···C(3)iii	2.9578
C(9)···H(12A)	3.4221	H(9B)···C(4)iii	2.9243
C(9)···H(12B)	2.7392	H(9B)···C(5)iii	3.2049
C(11)···H(9A)	2.9697	H(9B)···C(6)iii	3.4973
C(11)···H(9B)	2.6293	H(9B)···H(15B)ii	3.4627
C(12)···H(9A)	3.3820	H(9B)···H(16A)ii	3.1460
C(12)···H(9B)	2.6912	H(10)···C(8)vi	3.3147
C(13)···H(5)	2.5315	H(10)···C(11)iv	2.9874
C(13)···H(15A)	2.6793	H(10)···C(11)x	3.4165
C(13)···H(15B)	3.3759	H(10)···C(12)iv	3.0231
C(13)···H(16A)	3.3933	H(10)···C(16)xi	3.0002
C(13)···H(16B)	2.7007	H(10)···H(8A)vi	2.8381
C(15)···H(13A)	2.6862	H(10)···H(8B)vi	3.0967
C(15)···H(13B)	3.3697	H(10)···H(8C)vi	3.4987
C(16)···H(13A)	2.6193	H(10)···H(11A)iv	2.7913
C(16)···H(13B)	3.0514	H(10)···H(11A)x	3.0070
H(2)···H(9A)	2.1545	H(10)···H(11B)iv	3.2057
H(2)···H(9B)	2.4315	H(10)···H(11B)x	3.1032
H(5)···H(6)	2.3396	H(10)···H(12A)iv	3.2582
H(5)···H(13A)	2.2709	H(10)···H(12B)iv	2.8516
H(5)···H(13B)	2.3861	H(10)···H(16A)xi	3.0514
H(9A)···H(10)	2.4474	H(10)···H(16B)xi	2.3527
H(9A)···H(11A)	3.0045	H(11A)···O(3)iii	3.3990
H(9B)···H(10)	2.9237	H(11A)···C(9)iii	3.2119
H(9B)···H(11A)	2.4243	H(11A)···C(10)iii	3.3530
H(9B)···H(11B)	3.5652	H(11A)···C(10)xii	3.2863
H(9B)···H(12B)	2.5324	H(11A)···C(11)xii	3.0519
H(10)···H(11A)	2.9497	H(11A)···C(16)ii	3.5854
H(10)···H(11B)	2.4153	H(11A)···H(9A)iii	2.6402
H(10)···H(12A)	2.4108	H(11A)···H(9A)xii	3.5855
H(10)···H(12B)	2.9459	H(11A)···H(10)iii	2.7913
H(11A)···H(12A)	2.9435	H(11A)···H(10)xii	3.0070
H(11A)···H(12B)	2.4248	H(11A)···H(11A)x	3.3981
H(11B)···H(12A)	2.4247	H(11A)···H(11A)xii	3.3981
H(11B)···H(12B)	2.9436	H(11A)···H(11B)x	3.4694
H(13A)···H(14)	2.9227	H(11A)···H(11B)xii	2.5855
H(13A)···H(15A)	2.5272	H(11A)···H(16A)ii	2.8206
H(13A)···H(16A)	3.5547	H(11B)···C(9)xii	3.2146
H(13A)···H(16B)	2.4089	H(11B)···C(10)xii	3.1923
H(13B)···H(14)	2.4211	H(11B)···C(11)x	3.3599
H(13B)···H(16B)	3.1209	H(11B)···C(11)xii	3.3805
H(14)···H(15A)	2.9345	H(11B)···C(15)xiii	3.2233
H(14)···H(15B)	2.3983	H(11B)···C(16)xi	3.4476
H(14)···H(16A)	2.4103	H(11B)···C(16)xiii	3.5454
H(14)···H(16B)	2.9445	H(11B)···H(9A)xii	2.4769
H(15A)···H(16A)	2.9283	H(11B)···H(10)iii	3.2057
H(15A)···H(16B)	2.4063	H(11B)···H(10)xii	3.1032
H(15B)···H(16A)	2.4063	H(11B)···H(11A)x	2.5855
H(15B)···H(16B)	2.9283	H(11B)···H(11A)xii	3.4694
O(1)···H(5)i	2.8414	H(11B)···H(11B)x	3.3990
O(1)···H(8B)iv	3.1047	H(11B)···H(11B)xii	3.3990
O(1)···H(12A)ii	3.0988	H(11B)···H(15A)xiii	3.1240
O(1)···H(13A)i	2.7280	H(11B)···H(15B)xiii	3.0867
O(1)···H(13B)i	3.3183	H(11B)···H(16A)xi	2.9551
O(1)···H(14)ix	3.5071	H(11B)···H(16B)xi	3.1149
O(1)···H(15A)viii	3.4180	H(12A)···O(1)vi	3.0988
O(1)···H(16B)i	3.5118	H(12A)···C(8)vi	3.1867
O(2)···H(14)ix	2.8256	H(12A)···C(8)vii	3.1528
O(2)···H(14)ii	3.4119	H(12A)···C(15)xiii	3.3551
O(2)···H(15B)ii	2.8026	H(12A)···H(8A)vi	2.2901
O(3)···H(5)iii	3.5191	H(12A)···H(8B)vi	3.3323
O(3)···H(8A)vi	3.2735	H(12A)···H(8B)vii	2.4836
O(3)···H(8C)vi	3.1385	H(12A)···H(8C)vii	2.9798
O(3)···H(9B)iv	3.5250	H(12A)···H(10)iii	3.2582
O(3)···H(11A)iv	3.3990	H(12A)···H(15A)xiii	2.6428
O(3)···H(12B)iv	2.5506	H(12A)···H(16B)xi	2.7473
O(3)···H(13B)iii	2.9009	H(12A)···H(16B)xiii	3.3943
O(4)···H(8C)vi	2.7133	H(12B)···O(3)iii	2.5506
O(4)···H(9B)iv	3.4870	H(12B)···O(4)iii	2.6136
O(4)···H(12B)iv	2.6136	H(12B)···C(3)iii	2.9854
O(4)···H(13B)iii	3.0664	H(12B)···C(4)iii	3.0090
C(1)···H(5)i	3.1796	H(12B)···C(8)vii	3.0774
C(1)···H(6)i	3.4340	H(12B)···C(9)iii	3.3140
C(1)···H(9B)iv	3.5419	H(12B)···C(10)iii	3.4040
C(2)···H(6)iii	3.4221	H(12B)···C(13)iii	3.5333
C(2)···H(9B)iv	3.2847	H(12B)···H(8A)vi	2.9188
C(2)···H(15B)ii	3.4133	H(12B)···H(8A)vii	3.3617
C(3)···H(5)iii	3.3346	H(12B)···H(8B)vii	2.8849
C(3)···H(9B)iv	2.9578	H(12B)···H(8C)vii	2.5373
C(3)···H(12B)iv	2.9854	H(12B)···H(9A)iii	3.4008
C(3)···H(13B)iii	3.3947	H(12B)···H(10)iii	2.8516
C(4)···H(6)i	3.4694	H(12B)···H(13B)iii	3.5216
C(4)···H(9B)iv	2.9243	H(12B)···H(14)iii	3.4659
C(4)···H(12B)iv	3.0090	H(13A)···O(1)viii	2.7280
C(4)···H(13B)iii	3.4883	H(13A)···C(7)viii	3.2771
C(5)···H(6)i	2.9995	H(13A)···C(8)viii	3.5579
C(5)···H(9B)iv	3.2049	H(13A)···H(8B)viii	2.8266
C(6)···H(2)iv	3.3092	H(13A)···H(15A)iv	3.5566
C(6)···H(5)i	3.1287	H(13B)···O(1)viii	3.3183
C(6)···H(6)i	2.9886	H(13B)···O(3)iv	2.9009
C(6)···H(9B)iv	3.4973	H(13B)···O(4)iv	3.0664
C(7)···H(5)i	3.0449	H(13B)···C(3)iv	3.3947
C(7)···H(13A)i	3.2771	H(13B)···C(4)iv	3.4883
C(7)···H(14)ix	3.1360	H(13B)···H(8A)xiv	3.3436
C(8)···H(10)ii	3.3147	H(13B)···H(8C)xiv	3.2663
C(8)···H(12A)ii	3.1867	H(13B)···H(12B)iv	3.5216
C(8)···H(12A)v	3.1528	H(13B)···H(15A)iv	3.0552
C(8)···H(12B)v	3.0774	H(14)···O(1)xiv	3.5071
C(8)···H(13A)i	3.5579	H(14)···O(2)xiv	2.8256
C(8)···H(14)ix	3.0483	H(14)···O(2)vi	3.4119
C(8)···H(14)ii	3.2335	H(14)···C(7)xiv	3.1360
C(8)···H(15B)ii	3.3790	H(14)···C(8)xiv	3.0483
C(8)···H(16B)i	3.3736	H(14)···C(8)vi	3.2335
C(9)···H(11A)iv	3.2119	H(14)···H(8A)xiv	2.6278
C(9)···H(11B)x	3.2146	H(14)···H(8B)vi	3.5027
C(9)···H(12B)iv	3.3140	H(14)···H(8C)xiv	3.2138
C(9)···H(15B)ii	3.5885	H(14)···H(8C)vi	2.4852
C(10)···H(8A)vi	2.9685	H(14)···H(12B)iv	3.4659
C(10)···H(11A)iv	3.3530	H(14)···H(15B)iv	3.4109
C(10)···H(11A)x	3.2863	H(15A)···O(1)i	3.4180
C(10)···H(11B)x	3.1923	H(15A)···C(12)xv	3.4231
C(10)···H(12B)iv	3.4040	H(15A)···C(13)iii	3.5184
C(10)···H(16B)xi	3.1033	H(15A)···C(14)iii	3.4443
C(11)···H(9A)iii	3.4606	H(15A)···C(16)iii	3.0775
C(11)···H(9A)xii	3.3711	H(15A)···H(8B)viii	3.1979
C(11)···H(10)iii	2.9874	H(15A)···H(8C)vi	3.5154
C(11)···H(10)xii	3.4165	H(15A)···H(11B)xv	3.1240
C(11)···H(11A)x	3.0519	H(15A)···H(12A)xv	2.6428
C(11)···H(11B)x	3.3805	H(15A)···H(13A)iii	3.5566
C(11)···H(11B)xii	3.3599	H(15A)···H(13B)iii	3.0552
C(11)···H(16B)xi	3.4832	H(15A)···H(16A)iii	3.1351
C(12)···H(8A)vi	2.6574	H(15A)···H(16B)iii	2.7897
C(12)···H(8B)vii	3.0389	H(15B)···O(2)vi	2.8026
C(12)···H(8C)vii	3.1519	H(15B)···C(2)vi	3.4133
C(12)···H(10)iii	3.0231	H(15B)···C(8)vi	3.3790
C(12)···H(15A)xiii	3.4231	H(15B)···C(9)vi	3.5885
C(12)···H(16B)xi	3.2856	H(15B)···C(14)iii	3.5496
C(13)···H(8C)vi	3.3878	H(15B)···C(16)iii	3.1951
C(13)···H(12B)iv	3.5333	H(15B)···H(2)vi	2.5642
C(13)···H(15A)iv	3.5184	H(15B)···H(8C)vi	2.9371
C(14)···H(8A)xiv	3.4558	H(15B)···H(9A)vi	2.8173
C(14)···H(8C)vi	2.8694	H(15B)···H(9B)vi	3.4627
C(14)···H(15A)iv	3.4443	H(15B)···H(11B)xv	3.0867
C(14)···H(15B)iv	3.5496	H(15B)···H(14)iii	3.4109
C(15)···H(2)vi	3.5201	H(15B)···H(16A)iii	2.7897
C(15)···H(8C)vi	3.1254	H(15B)···H(16B)iii	3.3623
C(15)···H(9A)vi	3.5231	H(16A)···C(15)iv	3.3656
C(15)···H(11B)xv	3.2233	H(16A)···H(2)xiv	3.3954
C(15)···H(12A)xv	3.3551	H(16A)···H(9A)xiv	3.2426
C(15)···H(16A)iii	3.3656	H(16A)···H(9A)vi	3.4014
C(15)···H(16B)iii	3.4736	H(16A)···H(9B)vi	3.1460
C(16)···H(8B)viii	3.5151	H(16A)···H(10)xvi	3.0514
C(16)···H(10)xvi	3.0002	H(16A)···H(11A)vi	2.8206
C(16)···H(11A)vi	3.5854	H(16A)···H(11B)xvi	2.9551
C(16)···H(11B)xvi	3.4476	H(16A)···H(15A)iv	3.1351
C(16)···H(11B)xv	3.5454	H(16A)···H(15B)iv	2.7897
C(16)···H(15A)iv	3.0775	H(16B)···O(1)viii	3.5118
C(16)···H(15B)iv	3.1951	H(16B)···C(8)viii	3.3736
H(2)···C(6)iii	3.3092	H(16B)···C(10)xvi	3.1033
H(2)···C(15)ii	3.5201	H(16B)···C(11)xvi	3.4832
H(2)···H(6)iii	3.3350	H(16B)···C(12)xvi	3.2856
H(2)···H(15B)ii	2.5642	H(16B)···C(15)iv	3.4736
H(2)···H(16A)ix	3.3954	H(16B)···H(8A)viii	3.1585
H(5)···O(1)viii	2.8414	H(16B)···H(8B)viii	2.7043
H(5)···O(3)iv	3.5191	H(16B)···H(10)xvi	2.3527
H(5)···C(1)viii	3.1796	H(16B)···H(11B)xvi	3.1149
H(5)···C(3)iv	3.3346	H(16B)···H(12A)xvi	2.7473
H(5)···C(6)viii	3.1287	H(16B)···H(12A)xv	3.3943
H(5)···C(7)viii	3.0449	H(16B)···H(15A)iv	2.7897
H(5)···H(6)viii	2.9456	H(16B)···H(15B)iv	3.3623
H(5)···H(6)i	3.2433
C(7)—O(2)—C(8)	116.68 (12)	H(8A)—C(8)—H(8B)	109.475
C(3)—O(3)—C(9)	116.11 (9)	H(8A)—C(8)—H(8C)	109.468
C(4)—O(4)—C(13)	117.33 (10)	H(8B)—C(8)—H(8C)	109.472
C(2)—C(1)—C(6)	120.17 (12)	O(3)—C(9)—H(9A)	109.948
C(2)—C(1)—C(7)	120.42 (11)	O(3)—C(9)—H(9B)	109.953
C(6)—C(1)—C(7)	119.40 (11)	C(10)—C(9)—H(9A)	109.961
C(1)—C(2)—C(3)	120.30 (12)	C(10)—C(9)—H(9B)	109.956
O(3)—C(3)—C(2)	124.69 (11)	H(9A)—C(9)—H(9B)	108.328
O(3)—C(3)—C(4)	115.80 (10)	C(9)—C(10)—H(10)	116.366
C(2)—C(3)—C(4)	119.50 (11)	C(11)—C(10)—H(10)	116.367
O(4)—C(4)—C(3)	115.03 (11)	C(12)—C(10)—H(10)	116.375
O(4)—C(4)—C(5)	125.26 (12)	C(10)—C(11)—H(11A)	117.777
C(3)—C(4)—C(5)	119.71 (12)	C(10)—C(11)—H(11B)	117.773
C(4)—C(5)—C(6)	120.21 (12)	C(12)—C(11)—H(11A)	117.769
C(1)—C(6)—C(5)	120.09 (12)	C(12)—C(11)—H(11B)	117.772
O(1)—C(7)—O(2)	123.48 (12)	H(11A)—C(11)—H(11B)	114.909
O(1)—C(7)—C(1)	125.10 (12)	C(10)—C(12)—H(12A)	117.744
O(2)—C(7)—C(1)	111.42 (11)	C(10)—C(12)—H(12B)	117.746
O(3)—C(9)—C(10)	108.69 (9)	C(11)—C(12)—H(12A)	117.745
C(9)—C(10)—C(11)	116.52 (11)	C(11)—C(12)—H(12B)	117.747
C(9)—C(10)—C(12)	119.44 (11)	H(12A)—C(12)—H(12B)	114.871
C(11)—C(10)—C(12)	59.78 (9)	O(4)—C(13)—H(13A)	110.344
C(10)—C(11)—C(12)	59.97 (9)	O(4)—C(13)—H(13B)	110.344
C(10)—C(12)—C(11)	60.25 (9)	C(14)—C(13)—H(13A)	110.360
O(4)—C(13)—C(14)	106.85 (12)	C(14)—C(13)—H(13B)	110.358
C(13)—C(14)—C(15)	117.46 (14)	H(13A)—C(13)—H(13B)	108.585
C(13)—C(14)—C(16)	117.91 (14)	C(13)—C(14)—H(14)	116.594
C(15)—C(14)—C(16)	59.51 (12)	C(15)—C(14)—H(14)	116.598
C(14)—C(15)—C(16)	60.61 (12)	C(16)—C(14)—H(14)	116.603
C(14)—C(16)—C(15)	59.89 (12)	C(14)—C(15)—H(15A)	117.706
C(1)—C(2)—H(2)	119.856	C(14)—C(15)—H(15B)	117.711
C(3)—C(2)—H(2)	119.846	C(16)—C(15)—H(15A)	117.702
C(4)—C(5)—H(5)	119.900	C(16)—C(15)—H(15B)	117.720
C(6)—C(5)—H(5)	119.892	H(15A)—C(15)—H(15B)	114.826
C(1)—C(6)—H(6)	119.947	C(14)—C(16)—H(16A)	117.785
C(5)—C(6)—H(6)	119.960	C(14)—C(16)—H(16B)	117.794
O(2)—C(8)—H(8A)	109.469	C(15)—C(16)—H(16A)	117.781
O(2)—C(8)—H(8B)	109.474	C(15)—C(16)—H(16B)	117.788
O(2)—C(8)—H(8C)	109.470	H(16A)—C(16)—H(16B)	114.905
C(8)—O(2)—C(7)—O(1)	−2.4 (2)	C(2)—C(3)—C(4)—O(4)	179.31 (11)
C(8)—O(2)—C(7)—C(1)	177.99 (12)	C(2)—C(3)—C(4)—C(5)	−1.41 (19)
C(3)—O(3)—C(9)—C(10)	160.99 (10)	O(4)—C(4)—C(5)—C(6)	179.71 (12)
C(9)—O(3)—C(3)—C(2)	11.35 (17)	C(3)—C(4)—C(5)—C(6)	0.52 (20)
C(9)—O(3)—C(3)—C(4)	−167.98 (11)	C(4)—C(5)—C(6)—C(1)	0.69 (20)
C(4)—O(4)—C(13)—C(14)	177.72 (12)	O(3)—C(9)—C(10)—C(11)	153.94 (11)
C(13)—O(4)—C(4)—C(3)	177.39 (11)	O(3)—C(9)—C(10)—C(12)	85.31 (14)
C(13)—O(4)—C(4)—C(5)	−1.83 (19)	C(9)—C(10)—C(11)—C(12)	−110.19 (13)
C(2)—C(1)—C(6)—C(5)	−1.01 (19)	C(9)—C(10)—C(12)—C(11)	105.34 (13)
C(6)—C(1)—C(2)—C(3)	0.09 (19)	C(11)—C(10)—C(12)—C(11)	0.0
C(2)—C(1)—C(7)—O(1)	175.66 (13)	C(12)—C(10)—C(11)—C(12)	0.0
C(2)—C(1)—C(7)—O(2)	−4.76 (17)	C(10)—C(11)—C(12)—C(10)	0.0
C(7)—C(1)—C(2)—C(3)	−179.24 (12)	O(4)—C(13)—C(14)—C(15)	−76.77 (16)
C(6)—C(1)—C(7)—O(1)	−3.7 (2)	O(4)—C(13)—C(14)—C(16)	−144.94 (14)
C(6)—C(1)—C(7)—O(2)	175.90 (12)	C(13)—C(14)—C(15)—C(16)	−107.83 (16)
C(7)—C(1)—C(6)—C(5)	178.33 (12)	C(13)—C(14)—C(16)—C(15)	107.08 (17)
C(1)—C(2)—C(3)—O(3)	−178.20 (12)	C(15)—C(14)—C(16)—C(15)	0.0
C(1)—C(2)—C(3)—C(4)	1.11 (19)	C(16)—C(14)—C(15)—C(16)	0.0
O(3)—C(3)—C(4)—O(4)	−1.31 (17)	C(14)—C(15)—C(16)—C(14)	0.0
O(3)—C(3)—C(4)—C(5)	177.96 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O3iii	0.99	2.55	3.4073 (18)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯O3i	0.99	2.55	3.4073 (18)	145

Symmetry code: (i) .