Bis(1,2,2,6,6-penta­methyl­piperidin-4-yl) butyl­malonate

The title compound, C₂₇H₅₀N₂O₄, was prepared from butyl­malonic acid and 1,2,2,6,6-penta­methyl-4-hydroxy­piperidine by transesterification. In the mol­ecule, both piperidine rings adopt chair conformations.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.165
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.33 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C26    -   C27     ..       9.81 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C26    -   C27    ...       1.43 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) butylmalonate

Crystal data

C27H50N2O4	F(000) = 1032
Mr = 466.69	Dx = 1.084 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2068 reflections
a = 11.871 (3) Å	θ = 2.5–20.1°
b = 18.170 (4) Å	µ = 0.07 mm^−1
c = 13.260 (3) Å	T = 294 K
β = 91.386 (4)°	Block, colourless
V = 2859.4 (11) Å^3	0.22 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART-CCD area-detector diffractometer	5037 independent reflections
Radiation source: fine-focus sealed tube	2237 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.984, Tmax = 0.993	k = −20→21
14581 measured reflections	l = −15→11

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 0.2574P] where P = (Fo^2 + 2Fc^2)/3
5037 reflections	(Δ/σ)max = 0.002
309 parameters	Δρmax = 0.17 e Å^−3
6 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. ¹H NMR (C_DCl₃): δ 0.90 (t, 3H), 1.07 (s, 12H), 1.16 (s, 12H), 1.32 (m, 4H), 1.47 (m, 4H), 2.17 (s, 6H), 3.26 (t, 1H), 5.06 (m, 2H) ¹³C NMR (C_DCl₃): δ 14.04, 20.87, 22.58, 28.23, 28.58, 29.69, 33.38, 45.84, 45.91, 52.58, 55.41, 69.05, 169.50

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
O1	0.04402 (16)	0.01242 (10)	0.24909 (14)	0.0546 (6)
O2	−0.06481 (19)	−0.01622 (14)	0.37872 (18)	0.0859 (8)
O3	−0.00900 (15)	0.16230 (10)	0.17701 (13)	0.0481 (5)
O4	−0.12095 (16)	0.08696 (12)	0.08518 (16)	0.0666 (7)
N1	0.3419 (2)	−0.11008 (15)	0.2838 (2)	0.0665 (8)
N2	0.25314 (19)	0.22335 (13)	−0.01251 (18)	0.0536 (7)
C1	0.1203 (2)	−0.04904 (16)	0.2721 (2)	0.0512 (8)
H1	0.0769	−0.0934	0.2871	0.061*
C2	0.1994 (2)	−0.03125 (18)	0.3587 (2)	0.0630 (9)
H2A	0.1562	−0.0233	0.4189	0.076*
H2B	0.2391	0.0141	0.3441	0.076*
C3	0.2851 (3)	−0.0921 (2)	0.3791 (3)	0.0714 (10)
C4	0.2732 (3)	−0.12287 (18)	0.1898 (2)	0.0627 (9)
C5	0.1874 (2)	−0.06051 (17)	0.1791 (2)	0.0558 (8)
H5A	0.2267	−0.0153	0.1636	0.067*
H5B	0.1362	−0.0713	0.1229	0.067*
C6	0.2288 (3)	−0.1573 (2)	0.4318 (3)	0.1054 (14)
H6A	0.1682	−0.1758	0.3898	0.158*
H6B	0.1998	−0.1413	0.4951	0.158*
H6C	0.2833	−0.1956	0.4435	0.158*
C7	0.3746 (3)	−0.0599 (3)	0.4535 (3)	0.1080 (15)
H7A	0.4207	−0.0989	0.4804	0.162*
H7B	0.3376	−0.0353	0.5076	0.162*
H7C	0.4209	−0.0253	0.4187	0.162*
C8	0.4331 (3)	−0.1640 (2)	0.2960 (3)	0.1125 (16)
H8A	0.4884	−0.1457	0.3438	0.169*
H8B	0.4678	−0.1719	0.2322	0.169*
H8C	0.4030	−0.2096	0.3200	0.169*
C9	0.2120 (3)	−0.19751 (19)	0.1840 (3)	0.1016 (14)
H9A	0.2646	−0.2363	0.1991	0.152*
H9B	0.1805	−0.2044	0.1173	0.152*
H9C	0.1527	−0.1984	0.2320	0.152*
C10	0.3506 (3)	−0.1168 (2)	0.0988 (3)	0.0990 (13)
H10A	0.4003	−0.0755	0.1080	0.148*
H10B	0.3056	−0.1099	0.0384	0.148*
H10C	0.3941	−0.1610	0.0931	0.148*
C11	−0.0462 (2)	0.02021 (17)	0.3056 (2)	0.0543 (8)
C12	−0.1247 (2)	0.08026 (15)	0.2665 (2)	0.0493 (8)
H12	−0.1229	0.1209	0.3150	0.059*
C13	−0.0865 (2)	0.10931 (16)	0.1655 (2)	0.0468 (8)
C14	0.0492 (2)	0.18507 (14)	0.0858 (2)	0.0431 (7)
H14	−0.0052	0.1934	0.0302	0.052*
C15	0.1334 (2)	0.12755 (15)	0.0573 (2)	0.0473 (8)
H15A	0.0939	0.0822	0.0414	0.057*
H15B	0.1835	0.1181	0.1148	0.057*
C16	0.2035 (2)	0.14974 (15)	−0.0324 (2)	0.0479 (8)
C17	0.1804 (2)	0.28400 (15)	0.0243 (2)	0.0508 (8)
C18	0.1102 (2)	0.25464 (15)	0.1115 (2)	0.0495 (8)
H18A	0.1596	0.2460	0.1696	0.059*
H18B	0.0558	0.2918	0.1300	0.059*
C19	0.1320 (3)	0.14288 (18)	−0.1304 (2)	0.0699 (10)
H19A	0.0656	0.1727	−0.1255	0.105*
H19B	0.1105	0.0924	−0.1404	0.105*
H19C	0.1752	0.1592	−0.1864	0.105*
C20	0.2995 (2)	0.09311 (17)	−0.0382 (3)	0.0704 (10)
H20A	0.3380	0.0992	−0.1005	0.106*
H20B	0.2688	0.0443	−0.0350	0.106*
H20C	0.3516	0.1005	0.0174	0.106*
C21	0.3302 (3)	0.24753 (19)	−0.0912 (3)	0.0873 (12)
H21A	0.3814	0.2084	−0.1062	0.131*
H21B	0.3720	0.2897	−0.0678	0.131*
H21C	0.2874	0.2603	−0.1511	0.131*
C22	0.2570 (3)	0.34484 (17)	0.0697 (3)	0.0784 (11)
H22A	0.3123	0.3230	0.1145	0.118*
H22B	0.2121	0.3791	0.1064	0.118*
H22C	0.2943	0.3701	0.0164	0.118*
C23	0.1013 (3)	0.31988 (17)	−0.0566 (3)	0.0735 (10)
H23A	0.1447	0.3350	−0.1132	0.110*
H23B	0.0650	0.3620	−0.0282	0.110*
H23C	0.0453	0.2849	−0.0785	0.110*
C24	−0.2440 (2)	0.05032 (16)	0.2598 (2)	0.0596 (9)
H24A	−0.2486	0.0150	0.2051	0.071*
H24B	−0.2590	0.0241	0.3218	0.071*
C25	−0.3345 (2)	0.10691 (18)	0.2432 (3)	0.0699 (10)
H25A	−0.3172	0.1360	0.1842	0.084*
H25B	−0.3354	0.1398	0.3008	0.084*
C26	−0.4513 (3)	0.0722 (2)	0.2282 (3)	0.1040 (14)
H26A	−0.4529	0.0450	0.1652	0.125*
H26B	−0.4631	0.0372	0.2822	0.125*
C27	−0.5421 (3)	0.1237 (3)	0.2263 (4)	0.150 (2)
H27A	−0.5422	0.1503	0.2888	0.225*
H27B	−0.6122	0.0978	0.2174	0.225*
H27C	−0.5329	0.1575	0.1715	0.225*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0530 (13)	0.0568 (13)	0.0546 (13)	0.0093 (10)	0.0167 (11)	0.0061 (10)
O2	0.0750 (16)	0.110 (2)	0.0733 (17)	0.0065 (14)	0.0251 (14)	0.0392 (16)
O3	0.0491 (12)	0.0559 (12)	0.0397 (12)	−0.0090 (10)	0.0107 (9)	−0.0023 (10)
O4	0.0590 (14)	0.0953 (17)	0.0454 (14)	−0.0191 (12)	0.0024 (11)	−0.0089 (13)
N1	0.0501 (16)	0.092 (2)	0.0574 (18)	0.0143 (15)	−0.0066 (14)	0.0015 (16)
N2	0.0466 (15)	0.0598 (17)	0.0552 (17)	−0.0051 (13)	0.0161 (13)	0.0015 (13)
C1	0.0540 (19)	0.0520 (19)	0.048 (2)	0.0030 (16)	0.0045 (16)	0.0036 (16)
C2	0.061 (2)	0.083 (2)	0.045 (2)	−0.0008 (19)	0.0054 (17)	−0.0034 (18)
C3	0.056 (2)	0.104 (3)	0.054 (2)	0.003 (2)	−0.0083 (18)	0.013 (2)
C4	0.053 (2)	0.072 (2)	0.063 (2)	0.0140 (18)	−0.0050 (18)	−0.0073 (18)
C5	0.0567 (19)	0.067 (2)	0.0434 (19)	0.0112 (17)	−0.0030 (16)	−0.0051 (16)
C6	0.095 (3)	0.125 (3)	0.096 (3)	0.014 (3)	0.007 (3)	0.052 (3)
C7	0.085 (3)	0.169 (4)	0.069 (3)	−0.005 (3)	−0.021 (2)	−0.008 (3)
C8	0.078 (3)	0.159 (4)	0.099 (3)	0.046 (3)	−0.019 (2)	−0.002 (3)
C9	0.096 (3)	0.070 (3)	0.137 (4)	0.020 (2)	−0.030 (3)	−0.026 (3)
C10	0.081 (3)	0.145 (4)	0.070 (3)	0.046 (3)	0.007 (2)	−0.019 (3)
C11	0.051 (2)	0.066 (2)	0.047 (2)	−0.0058 (17)	0.0126 (17)	−0.0004 (18)
C12	0.0451 (18)	0.0535 (19)	0.0499 (19)	−0.0011 (15)	0.0160 (15)	−0.0053 (16)
C13	0.0407 (18)	0.055 (2)	0.045 (2)	0.0029 (16)	0.0082 (15)	−0.0023 (16)
C14	0.0447 (17)	0.0499 (18)	0.0352 (17)	−0.0035 (15)	0.0088 (14)	0.0027 (14)
C15	0.0480 (17)	0.0481 (18)	0.0461 (19)	−0.0022 (15)	0.0055 (15)	0.0002 (15)
C16	0.0499 (18)	0.0517 (19)	0.0426 (18)	−0.0023 (15)	0.0074 (15)	−0.0024 (15)
C17	0.0511 (18)	0.0476 (18)	0.054 (2)	−0.0032 (16)	0.0061 (16)	0.0016 (16)
C18	0.0490 (17)	0.0501 (19)	0.0496 (19)	0.0025 (15)	0.0090 (15)	−0.0026 (15)
C19	0.079 (2)	0.085 (2)	0.045 (2)	−0.007 (2)	0.0040 (18)	−0.0071 (18)
C20	0.062 (2)	0.072 (2)	0.078 (2)	0.0142 (18)	0.0217 (18)	−0.0079 (19)
C21	0.079 (2)	0.091 (3)	0.094 (3)	−0.020 (2)	0.046 (2)	−0.001 (2)
C22	0.077 (2)	0.064 (2)	0.095 (3)	−0.0210 (19)	0.012 (2)	−0.012 (2)
C23	0.083 (2)	0.065 (2)	0.073 (2)	0.0090 (19)	0.007 (2)	0.0176 (19)
C24	0.0525 (19)	0.066 (2)	0.061 (2)	−0.0128 (17)	0.0200 (16)	−0.0091 (17)
C25	0.047 (2)	0.081 (2)	0.082 (3)	0.0013 (18)	0.0116 (18)	−0.017 (2)
C26	0.055 (2)	0.117 (3)	0.140 (4)	0.005 (2)	0.005 (2)	−0.027 (3)
C27	0.086 (3)	0.190 (5)	0.173 (5)	0.002 (3)	−0.007 (3)	−0.053 (4)

Geometric parameters (Å, º)

O1—C11	1.329 (3)	C12—C13	1.520 (4)
O1—C1	1.465 (3)	C12—H12	0.9800
O2—C11	1.199 (3)	C14—C18	1.492 (3)
O3—C13	1.338 (3)	C14—C15	1.501 (3)
O3—C14	1.467 (3)	C14—H14	0.9800
O4—C13	1.202 (3)	C15—C16	1.523 (4)
N1—C8	1.466 (4)	C15—H15A	0.9700
N1—C3	1.483 (4)	C15—H15B	0.9700
N1—C4	1.491 (4)	C16—C20	1.539 (4)
N2—C21	1.471 (4)	C16—C19	1.540 (4)
N2—C16	1.483 (3)	C17—C18	1.537 (4)
N2—C17	1.490 (3)	C17—C22	1.544 (4)
C1—C5	1.498 (4)	C17—C23	1.552 (4)
C1—C2	1.502 (4)	C18—H18A	0.9700
C1—H1	0.9800	C18—H18B	0.9700
C2—C3	1.522 (4)	C19—H19A	0.9600
C2—H2A	0.9700	C19—H19B	0.9600
C2—H2B	0.9700	C19—H19C	0.9600
C3—C6	1.536 (5)	C20—H20A	0.9600
C3—C7	1.548 (4)	C20—H20B	0.9600
C4—C5	1.528 (4)	C20—H20C	0.9600
C4—C10	1.538 (4)	C21—H21A	0.9600
C4—C9	1.540 (4)	C21—H21B	0.9600
C5—H5A	0.9700	C21—H21C	0.9600
C5—H5B	0.9700	C22—H22A	0.9600
C6—H6A	0.9600	C22—H22B	0.9600
C6—H6B	0.9600	C22—H22C	0.9600
C6—H6C	0.9600	C23—H23A	0.9600
C7—H7A	0.9600	C23—H23B	0.9600
C7—H7B	0.9600	C23—H23C	0.9600
C7—H7C	0.9600	C24—C25	1.499 (4)
C8—H8A	0.9600	C24—H24A	0.9700
C8—H8B	0.9600	C24—H24B	0.9700
C8—H8C	0.9600	C25—C26	1.533 (4)
C9—H9A	0.9600	C25—H25A	0.9700
C9—H9B	0.9600	C25—H25B	0.9700
C9—H9C	0.9600	C26—C27	1.426 (5)
C10—H10A	0.9600	C26—H26A	0.9700
C10—H10B	0.9600	C26—H26B	0.9700
C10—H10C	0.9600	C27—H27A	0.9600
C11—C12	1.518 (4)	C27—H27B	0.9600
C12—C24	1.517 (4)	C27—H27C	0.9600
C11—O1—C1	117.8 (2)	C18—C14—C15	109.0 (2)
C13—O3—C14	116.4 (2)	O3—C14—H14	110.4
C8—N1—C3	113.7 (3)	C18—C14—H14	110.4
C8—N1—C4	112.1 (3)	C15—C14—H14	110.4
C3—N1—C4	119.7 (2)	C14—C15—C16	113.1 (2)
C21—N2—C16	113.2 (2)	C14—C15—H15A	109.0
C21—N2—C17	112.8 (2)	C16—C15—H15A	109.0
C16—N2—C17	119.6 (2)	C14—C15—H15B	109.0
O1—C1—C5	105.8 (2)	C16—C15—H15B	109.0
O1—C1—C2	111.5 (2)	H15A—C15—H15B	107.8
C5—C1—C2	108.9 (2)	N2—C16—C15	108.8 (2)
O1—C1—H1	110.2	N2—C16—C20	108.7 (2)
C5—C1—H1	110.2	C15—C16—C20	106.3 (2)
C2—C1—H1	110.2	N2—C16—C19	115.6 (2)
C1—C2—C3	112.5 (3)	C15—C16—C19	109.7 (2)
C1—C2—H2A	109.1	C20—C16—C19	107.3 (2)
C3—C2—H2A	109.1	N2—C17—C18	108.6 (2)
C1—C2—H2B	109.1	N2—C17—C22	108.4 (2)
C3—C2—H2B	109.1	C18—C17—C22	106.3 (2)
H2A—C2—H2B	107.8	N2—C17—C23	115.5 (2)
N1—C3—C2	108.9 (3)	C18—C17—C23	109.6 (2)
N1—C3—C6	115.5 (3)	C22—C17—C23	108.0 (2)
C2—C3—C6	110.2 (3)	C14—C18—C17	113.0 (2)
N1—C3—C7	107.9 (3)	C14—C18—H18A	109.0
C2—C3—C7	106.4 (3)	C17—C18—H18A	109.0
C6—C3—C7	107.5 (3)	C14—C18—H18B	109.0
N1—C4—C5	108.2 (2)	C17—C18—H18B	109.0
N1—C4—C10	108.6 (3)	H18A—C18—H18B	107.8
C5—C4—C10	106.5 (3)	C16—C19—H19A	109.5
N1—C4—C9	115.3 (3)	C16—C19—H19B	109.5
C5—C4—C9	109.6 (2)	H19A—C19—H19B	109.5
C10—C4—C9	108.3 (3)	C16—C19—H19C	109.5
C1—C5—C4	113.2 (2)	H19A—C19—H19C	109.5
C1—C5—H5A	108.9	H19B—C19—H19C	109.5
C4—C5—H5A	108.9	C16—C20—H20A	109.5
C1—C5—H5B	108.9	C16—C20—H20B	109.5
C4—C5—H5B	108.9	H20A—C20—H20B	109.5
H5A—C5—H5B	107.8	C16—C20—H20C	109.5
C3—C6—H6A	109.5	H20A—C20—H20C	109.5
C3—C6—H6B	109.5	H20B—C20—H20C	109.5
H6A—C6—H6B	109.5	N2—C21—H21A	109.5
C3—C6—H6C	109.5	N2—C21—H21B	109.5
H6A—C6—H6C	109.5	H21A—C21—H21B	109.5
H6B—C6—H6C	109.5	N2—C21—H21C	109.5
C3—C7—H7A	109.5	H21A—C21—H21C	109.5
C3—C7—H7B	109.5	H21B—C21—H21C	109.5
H7A—C7—H7B	109.5	C17—C22—H22A	109.5
C3—C7—H7C	109.5	C17—C22—H22B	109.5
H7A—C7—H7C	109.5	H22A—C22—H22B	109.5
H7B—C7—H7C	109.5	C17—C22—H22C	109.5
N1—C8—H8A	109.5	H22A—C22—H22C	109.5
N1—C8—H8B	109.5	H22B—C22—H22C	109.5
H8A—C8—H8B	109.5	C17—C23—H23A	109.5
N1—C8—H8C	109.5	C17—C23—H23B	109.5
H8A—C8—H8C	109.5	H23A—C23—H23B	109.5
H8B—C8—H8C	109.5	C17—C23—H23C	109.5
C4—C9—H9A	109.5	H23A—C23—H23C	109.5
C4—C9—H9B	109.5	H23B—C23—H23C	109.5
H9A—C9—H9B	109.5	C25—C24—C12	115.3 (2)
C4—C9—H9C	109.5	C25—C24—H24A	108.5
H9A—C9—H9C	109.5	C12—C24—H24A	108.5
H9B—C9—H9C	109.5	C25—C24—H24B	108.5
C4—C10—H10A	109.5	C12—C24—H24B	108.5
C4—C10—H10B	109.5	H24A—C24—H24B	107.5
H10A—C10—H10B	109.5	C24—C25—C26	112.3 (3)
C4—C10—H10C	109.5	C24—C25—H25A	109.1
H10A—C10—H10C	109.5	C26—C25—H25A	109.1
H10B—C10—H10C	109.5	C24—C25—H25B	109.1
O2—C11—O1	124.3 (3)	C26—C25—H25B	109.1
O2—C11—C12	123.3 (3)	H25A—C25—H25B	107.9
O1—C11—C12	112.4 (3)	C27—C26—C25	114.4 (4)
C24—C12—C11	109.1 (2)	C27—C26—H26A	108.7
C24—C12—C13	111.8 (2)	C25—C26—H26A	108.7
C11—C12—C13	110.9 (2)	C27—C26—H26B	108.7
C24—C12—H12	108.3	C25—C26—H26B	108.7
C11—C12—H12	108.3	H26A—C26—H26B	107.6
C13—C12—H12	108.3	C26—C27—H27A	109.5
O4—C13—O3	124.3 (3)	C26—C27—H27B	109.5
O4—C13—C12	124.1 (3)	H27A—C27—H27B	109.5
O3—C13—C12	111.6 (3)	C26—C27—H27C	109.5
O3—C14—C18	106.6 (2)	H27A—C27—H27C	109.5
O3—C14—C15	109.9 (2)	H27B—C27—H27C	109.5
C11—O1—C1—C5	160.6 (2)	C24—C12—C13—O4	−28.1 (4)
C11—O1—C1—C2	−81.1 (3)	C11—C12—C13—O4	93.9 (3)
O1—C1—C2—C3	−175.8 (2)	C24—C12—C13—O3	152.5 (2)
C5—C1—C2—C3	−59.4 (3)	C11—C12—C13—O3	−85.5 (3)
C8—N1—C3—C2	175.2 (3)	C13—O3—C14—C18	167.3 (2)
C4—N1—C3—C2	−48.4 (4)	C13—O3—C14—C15	−74.8 (3)
C8—N1—C3—C6	−60.2 (4)	O3—C14—C15—C16	−175.8 (2)
C4—N1—C3—C6	76.1 (4)	C18—C14—C15—C16	−59.3 (3)
C8—N1—C3—C7	60.1 (4)	C21—N2—C16—C15	175.3 (2)
C4—N1—C3—C7	−163.6 (3)	C17—N2—C16—C15	−47.9 (3)
C1—C2—C3—N1	52.4 (3)	C21—N2—C16—C20	60.0 (3)
C1—C2—C3—C6	−75.3 (4)	C17—N2—C16—C20	−163.3 (2)
C1—C2—C3—C7	168.4 (3)	C21—N2—C16—C19	−60.7 (3)
C8—N1—C4—C5	−175.2 (3)	C17—N2—C16—C19	76.0 (3)
C3—N1—C4—C5	47.8 (4)	C14—C15—C16—N2	52.1 (3)
C8—N1—C4—C10	−60.0 (4)	C14—C15—C16—C20	169.0 (2)
C3—N1—C4—C10	162.9 (3)	C14—C15—C16—C19	−75.2 (3)
C8—N1—C4—C9	61.7 (4)	C21—N2—C17—C18	−175.6 (2)
C3—N1—C4—C9	−75.3 (4)	C16—N2—C17—C18	47.4 (3)
O1—C1—C5—C4	179.5 (2)	C21—N2—C17—C22	−60.6 (3)
C2—C1—C5—C4	59.4 (3)	C16—N2—C17—C22	162.5 (2)
N1—C4—C5—C1	−51.7 (3)	C21—N2—C17—C23	60.8 (3)
C10—C4—C5—C1	−168.3 (3)	C16—N2—C17—C23	−76.1 (3)
C9—C4—C5—C1	74.7 (3)	O3—C14—C18—C17	177.4 (2)
C1—O1—C11—O2	5.9 (4)	C15—C14—C18—C17	58.8 (3)
C1—O1—C11—C12	−173.4 (2)	N2—C17—C18—C14	−51.4 (3)
O2—C11—C12—C24	−48.8 (4)	C22—C17—C18—C14	−167.9 (2)
O1—C11—C12—C24	130.5 (3)	C23—C17—C18—C14	75.6 (3)
O2—C11—C12—C13	−172.4 (3)	C11—C12—C24—C25	167.8 (3)
O1—C11—C12—C13	7.0 (3)	C13—C12—C24—C25	−69.2 (3)
C14—O3—C13—O4	−10.2 (4)	C12—C24—C25—C26	175.1 (3)
C14—O3—C13—C12	169.1 (2)	C24—C25—C26—C27	171.5 (4)