Crystal structure of 2-(2,6-diiso­propyl­phen­yl)-N,N-diethyl-3,3-dimethyl-2-aza­spiro­[4.5]decan-1-amine: a di­ethyl­amine adduct of a cyclic(alk­yl)(amino)­carbene (CAAC)

The structure of the title compound, C₂₇H₄₆N₂, at 93 K has monoclinic (P2₁/n) symmetry. The title compound was prepared by treatment of 2-(2,6-diiso­propyl­phenyl)-3,3-dimethyl-2-aza­spiro­[4.5]dec-1-en-2-ium hydrogen dichloride with two equivalents of lithium di­ethyl­amide. Characterization of the title compound by single-crystal X-ray diffraction and ¹H and ¹³C NMR spectroscopy is presented. Formation of the di­ethyl­amine adduct of the cyclic(alk­yl)(amino)­carbene (CAAC) was unexpected, as deprotonation using lithium diiso­propyl­amide results in free CAAC formation.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.121
• Data-to-parameter ratio = 25.0

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          S Verify
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         21 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014/4 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-(2,6-Diisopropylphenyl)-N,N-diethyl-3,3-dimethyl-2-azaspiro[4.5]decan-1-amine

Crystal data

C27H46N2	F(000) = 888
Mr = 398.66	Dx = 1.102 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.3319 (11) Å	Cell parameters from 9991 reflections
b = 14.4082 (13) Å	θ = 2.2–30.5°
c = 13.6155 (12) Å	µ = 0.06 mm^−1
β = 96.4589 (16)°	T = 93 K
V = 2403.9 (4) Å^3	Irregular, colorless
Z = 4	0.25 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer	5087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
φ and ω scans	θmax = 29.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −17→17
Tmin = 0.823, Tmax = 0.862	k = −20→20
57200 measured reflections	l = −18→18
6744 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 1.1815P] where P = (Fo^2 + 2Fc^2)/3
6744 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

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. A colorless crystal of approximate dimensions 0.191 x 0.248 x 0.250 mm was mounted in a cryoloop and transferred to a Bruker SMART APEX II diffractometer. The APEX2 program package was used to determine the unit-cell parameters and for data collection (25 sec/frame scan time). The raw frame data was processed using SAINT and SADABS to yield the reflection data file. Subsequent calculations were carried out using the SHELXTL program package. The diffraction symmetry was 2/m and the systematic absences were consistent with the monoclinic space group P21/n that was later determined to be correct.

The structure was solved by direct methods and refined on F2 by full-matrix least-squares techniques. The analytical scattering factors for neutral atoms were used throughout the analysis. Hydrogen atoms were included using a riding model.

Least-squares analysis yielded wR2 = 0.1207 and Goof = 1.018 for 270 variables refined against 6744 data (0.72 ), R1 = 0.0482 for those 5087 data with I > 2.0sigma(I).

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

	x	y	z	Uiso*/Ueq
N1	0.21509 (8)	0.23294 (7)	0.51919 (7)	0.0098 (2)
N2	0.19958 (8)	0.23854 (7)	0.33444 (7)	0.0116 (2)
C1	0.26502 (9)	0.25804 (8)	0.42898 (8)	0.0098 (2)
H1A	0.2755	0.3269	0.4316	0.012*
C2	0.38287 (9)	0.21455 (8)	0.44118 (8)	0.0100 (2)
C3	0.40228 (9)	0.19144 (8)	0.55256 (8)	0.0116 (2)
H3A	0.4473	0.1347	0.5633	0.014*
H3B	0.4410	0.2432	0.5892	0.014*
C4	0.28990 (9)	0.17623 (8)	0.58916 (9)	0.0112 (2)
C5	0.46257 (10)	0.28977 (8)	0.41182 (9)	0.0127 (2)
H5A	0.4390	0.3100	0.3433	0.015*
H5B	0.4585	0.3442	0.4556	0.015*
C6	0.58148 (10)	0.25689 (9)	0.41836 (9)	0.0149 (2)
H6A	0.6277	0.3075	0.3970	0.018*
H6B	0.6078	0.2413	0.4878	0.018*
C7	0.59148 (10)	0.17188 (9)	0.35313 (9)	0.0149 (2)
H7A	0.6677	0.1492	0.3614	0.018*
H7B	0.5725	0.1890	0.2829	0.018*
C8	0.51526 (10)	0.09514 (9)	0.38112 (9)	0.0140 (2)
H8A	0.5397	0.0735	0.4490	0.017*
H8B	0.5193	0.0419	0.3357	0.017*
C9	0.39694 (9)	0.12857 (8)	0.37605 (9)	0.0122 (2)
H9A	0.3512	0.0775	0.3973	0.015*
H9B	0.3703	0.1438	0.3066	0.015*
C10	0.25722 (10)	0.07300 (8)	0.58361 (9)	0.0144 (2)
H10A	0.1848	0.0655	0.6058	0.022*
H10B	0.3107	0.0366	0.6262	0.022*
H10C	0.2554	0.0512	0.5152	0.022*
C11	0.29103 (10)	0.20714 (9)	0.69696 (9)	0.0141 (2)
H11A	0.3137	0.2723	0.7032	0.021*
H11B	0.3424	0.1685	0.7392	0.021*
H11C	0.2177	0.2004	0.7174	0.021*
C12	0.12797 (10)	0.31610 (9)	0.29816 (9)	0.0152 (3)
H12A	0.1066	0.3513	0.3554	0.018*
H12B	0.0607	0.2908	0.2612	0.018*
C13	0.18274 (12)	0.38151 (10)	0.23150 (11)	0.0228 (3)
H13A	0.1331	0.4328	0.2110	0.034*
H13B	0.2006	0.3477	0.1730	0.034*
H13C	0.2498	0.4062	0.2675	0.034*
C14	0.14360 (10)	0.14878 (9)	0.32281 (9)	0.0142 (2)
H14A	0.0682	0.1555	0.3404	0.017*
H14B	0.1821	0.1031	0.3686	0.017*
C15	0.13992 (11)	0.11302 (10)	0.21688 (9)	0.0196 (3)
H15A	0.1024	0.0530	0.2114	0.029*
H15B	0.2145	0.1056	0.1997	0.029*
H15C	0.1005	0.1575	0.1716	0.029*
C16	0.13925 (9)	0.29785 (8)	0.55420 (8)	0.0101 (2)
C17	0.16954 (10)	0.39033 (8)	0.58137 (8)	0.0118 (2)
C18	0.08998 (10)	0.45134 (9)	0.60845 (9)	0.0150 (2)
H18A	0.1097	0.5136	0.6250	0.018*
C19	−0.01697 (10)	0.42321 (9)	0.61176 (9)	0.0167 (3)
H19A	−0.0700	0.4659	0.6298	0.020*
C20	−0.04562 (10)	0.33259 (9)	0.58858 (9)	0.0153 (3)
H20A	−0.1185	0.3129	0.5927	0.018*
C21	0.03019 (10)	0.26912 (8)	0.55924 (8)	0.0117 (2)
C22	0.28572 (10)	0.42758 (8)	0.58449 (9)	0.0124 (2)
H22A	0.3346	0.3746	0.5717	0.015*
C23	0.29540 (11)	0.50154 (9)	0.50440 (9)	0.0173 (3)
H23A	0.2704	0.4754	0.4393	0.026*
H23B	0.3717	0.5210	0.5060	0.026*
H23C	0.2503	0.5553	0.5169	0.026*
C24	0.32675 (11)	0.46913 (10)	0.68579 (10)	0.0192 (3)
H24A	0.3178	0.4235	0.7377	0.029*
H24B	0.2845	0.5250	0.6970	0.029*
H24C	0.4041	0.4854	0.6873	0.029*
C25	−0.00794 (10)	0.17054 (9)	0.53442 (9)	0.0134 (2)
H25A	0.0520	0.1375	0.5050	0.016*
C26	−0.10981 (11)	0.16883 (10)	0.45862 (10)	0.0213 (3)
H26A	−0.0967	0.2062	0.4010	0.032*
H26B	−0.1720	0.1944	0.4886	0.032*
H26C	−0.1259	0.1047	0.4378	0.032*
C27	−0.03084 (11)	0.11760 (10)	0.62790 (10)	0.0207 (3)
H27A	0.0339	0.1199	0.6767	0.031*
H27B	−0.0484	0.0528	0.6109	0.031*
H27C	−0.0926	0.1464	0.6557	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0099 (4)	0.0105 (5)	0.0093 (4)	0.0021 (4)	0.0023 (3)	0.0011 (4)
N2	0.0117 (5)	0.0120 (5)	0.0107 (4)	0.0014 (4)	−0.0009 (4)	−0.0001 (4)
C1	0.0103 (5)	0.0100 (5)	0.0090 (5)	0.0001 (4)	0.0015 (4)	−0.0003 (4)
C2	0.0083 (5)	0.0106 (5)	0.0111 (5)	0.0006 (4)	0.0013 (4)	−0.0005 (4)
C3	0.0102 (5)	0.0128 (6)	0.0116 (5)	0.0012 (4)	0.0007 (4)	0.0007 (4)
C4	0.0106 (5)	0.0111 (5)	0.0117 (5)	0.0019 (4)	0.0010 (4)	0.0015 (4)
C5	0.0122 (5)	0.0120 (6)	0.0144 (5)	−0.0019 (4)	0.0036 (4)	−0.0015 (4)
C6	0.0105 (5)	0.0172 (6)	0.0171 (6)	−0.0029 (5)	0.0024 (4)	−0.0028 (5)
C7	0.0101 (5)	0.0177 (6)	0.0172 (6)	−0.0002 (5)	0.0028 (4)	−0.0027 (5)
C8	0.0124 (6)	0.0134 (6)	0.0167 (6)	0.0018 (4)	0.0032 (4)	−0.0030 (5)
C9	0.0105 (5)	0.0120 (6)	0.0144 (5)	−0.0001 (4)	0.0026 (4)	−0.0026 (4)
C10	0.0141 (6)	0.0124 (6)	0.0169 (6)	0.0017 (5)	0.0031 (5)	0.0028 (5)
C11	0.0157 (6)	0.0161 (6)	0.0105 (5)	0.0028 (5)	0.0017 (4)	0.0019 (4)
C12	0.0137 (6)	0.0179 (6)	0.0137 (6)	0.0049 (5)	−0.0004 (4)	0.0014 (5)
C13	0.0246 (7)	0.0209 (7)	0.0232 (7)	0.0059 (6)	0.0034 (5)	0.0080 (5)
C14	0.0133 (6)	0.0154 (6)	0.0137 (5)	−0.0011 (5)	0.0009 (4)	−0.0031 (5)
C15	0.0187 (6)	0.0234 (7)	0.0163 (6)	−0.0020 (5)	−0.0004 (5)	−0.0069 (5)
C16	0.0111 (5)	0.0113 (5)	0.0078 (5)	0.0028 (4)	0.0012 (4)	0.0009 (4)
C17	0.0131 (5)	0.0130 (6)	0.0092 (5)	0.0018 (4)	0.0009 (4)	0.0004 (4)
C18	0.0190 (6)	0.0123 (6)	0.0137 (6)	0.0027 (5)	0.0020 (5)	0.0000 (4)
C19	0.0158 (6)	0.0190 (6)	0.0157 (6)	0.0085 (5)	0.0039 (5)	0.0009 (5)
C20	0.0113 (5)	0.0200 (6)	0.0148 (6)	0.0030 (5)	0.0021 (4)	0.0020 (5)
C21	0.0118 (5)	0.0143 (6)	0.0091 (5)	0.0011 (4)	0.0009 (4)	0.0010 (4)
C22	0.0142 (6)	0.0109 (6)	0.0121 (5)	−0.0001 (4)	0.0016 (4)	−0.0022 (4)
C23	0.0217 (7)	0.0123 (6)	0.0182 (6)	−0.0023 (5)	0.0034 (5)	0.0001 (5)
C24	0.0210 (6)	0.0187 (6)	0.0172 (6)	0.0004 (5)	−0.0009 (5)	−0.0060 (5)
C25	0.0109 (5)	0.0158 (6)	0.0137 (5)	−0.0011 (4)	0.0023 (4)	0.0004 (5)
C26	0.0147 (6)	0.0260 (7)	0.0223 (7)	−0.0025 (5)	−0.0024 (5)	−0.0035 (5)
C27	0.0192 (6)	0.0220 (7)	0.0219 (7)	−0.0027 (5)	0.0065 (5)	0.0046 (5)

Geometric parameters (Å, º)

N1—C16	1.4412 (15)	C13—H13A	0.9800
N1—C1	1.4794 (15)	C13—H13B	0.9800
N1—C4	1.4928 (15)	C13—H13C	0.9800
N2—C14	1.4662 (16)	C14—C15	1.5274 (17)
N2—C1	1.4675 (14)	C14—H14A	0.9900
N2—C12	1.4745 (15)	C14—H14B	0.9900
C1—C2	1.5741 (16)	C15—H15A	0.9800
C1—H1A	1.0000	C15—H15B	0.9800
C2—C3	1.5449 (16)	C15—H15C	0.9800
C2—C9	1.5445 (16)	C16—C21	1.4162 (16)
C2—C5	1.5456 (16)	C16—C17	1.4215 (17)
C3—C4	1.5402 (16)	C17—C18	1.3974 (17)
C3—H3A	0.9900	C17—C22	1.5260 (17)
C3—H3B	0.9900	C18—C19	1.3853 (18)
C4—C11	1.5324 (17)	C18—H18A	0.9500
C4—C10	1.5406 (17)	C19—C20	1.3800 (19)
C5—C6	1.5340 (17)	C19—H19A	0.9500
C5—H5A	0.9900	C20—C21	1.3978 (17)
C5—H5B	0.9900	C20—H20A	0.9500
C6—C7	1.5260 (17)	C21—C25	1.5222 (17)
C6—H6A	0.9900	C22—C24	1.5361 (17)
C6—H6B	0.9900	C22—C23	1.5390 (17)
C7—C8	1.5271 (18)	C22—H22A	1.0000
C7—H7A	0.9900	C23—H23A	0.9800
C7—H7B	0.9900	C23—H23B	0.9800
C8—C9	1.5307 (16)	C23—H23C	0.9800
C8—H8A	0.9900	C24—H24A	0.9800
C8—H8B	0.9900	C24—H24B	0.9800
C9—H9A	0.9900	C24—H24C	0.9800
C9—H9B	0.9900	C25—C26	1.5337 (17)
C10—H10A	0.9800	C25—C27	1.5370 (18)
C10—H10B	0.9800	C25—H25A	1.0000
C10—H10C	0.9800	C26—H26A	0.9800
C11—H11A	0.9800	C26—H26B	0.9800
C11—H11B	0.9800	C26—H26C	0.9800
C11—H11C	0.9800	C27—H27A	0.9800
C12—C13	1.5186 (19)	C27—H27B	0.9800
C12—H12A	0.9900	C27—H27C	0.9800
C12—H12B	0.9900
C16—N1—C1	117.52 (9)	N2—C12—H12B	109.1
C16—N1—C4	121.44 (9)	C13—C12—H12B	109.1
C1—N1—C4	112.25 (9)	H12A—C12—H12B	107.9
C14—N2—C1	117.99 (9)	C12—C13—H13A	109.5
C14—N2—C12	112.05 (9)	C12—C13—H13B	109.5
C1—N2—C12	113.47 (9)	H13A—C13—H13B	109.5
N2—C1—N1	116.25 (9)	C12—C13—H13C	109.5
N2—C1—C2	115.24 (9)	H13A—C13—H13C	109.5
N1—C1—C2	106.30 (9)	H13B—C13—H13C	109.5
N2—C1—H1A	106.1	N2—C14—C15	111.30 (10)
N1—C1—H1A	106.1	N2—C14—H14A	109.4
C2—C1—H1A	106.1	C15—C14—H14A	109.4
C3—C2—C9	112.07 (10)	N2—C14—H14B	109.4
C3—C2—C5	111.85 (9)	C15—C14—H14B	109.4
C9—C2—C5	107.34 (9)	H14A—C14—H14B	108.0
C3—C2—C1	103.21 (9)	C14—C15—H15A	109.5
C9—C2—C1	114.88 (9)	C14—C15—H15B	109.5
C5—C2—C1	107.46 (9)	H15A—C15—H15B	109.5
C4—C3—C2	107.61 (9)	C14—C15—H15C	109.5
C4—C3—H3A	110.2	H15A—C15—H15C	109.5
C2—C3—H3A	110.2	H15B—C15—H15C	109.5
C4—C3—H3B	110.2	C21—C16—C17	118.98 (11)
C2—C3—H3B	110.2	C21—C16—N1	118.78 (10)
H3A—C3—H3B	108.5	C17—C16—N1	122.22 (10)
N1—C4—C11	112.99 (10)	C18—C17—C16	119.12 (11)
N1—C4—C3	103.28 (9)	C18—C17—C22	117.14 (11)
C11—C4—C3	110.91 (10)	C16—C17—C22	123.73 (10)
N1—C4—C10	110.96 (9)	C19—C18—C17	121.59 (12)
C11—C4—C10	107.56 (10)	C19—C18—H18A	119.2
C3—C4—C10	111.18 (10)	C17—C18—H18A	119.2
C6—C5—C2	113.58 (10)	C20—C19—C18	119.31 (12)
C6—C5—H5A	108.8	C20—C19—H19A	120.3
C2—C5—H5A	108.8	C18—C19—H19A	120.3
C6—C5—H5B	108.8	C19—C20—C21	121.47 (12)
C2—C5—H5B	108.8	C19—C20—H20A	119.3
H5A—C5—H5B	107.7	C21—C20—H20A	119.3
C7—C6—C5	110.69 (10)	C20—C21—C16	119.47 (11)
C7—C6—H6A	109.5	C20—C21—C25	118.29 (11)
C5—C6—H6A	109.5	C16—C21—C25	122.23 (11)
C7—C6—H6B	109.5	C17—C22—C24	112.06 (10)
C5—C6—H6B	109.5	C17—C22—C23	111.79 (10)
H6A—C6—H6B	108.1	C24—C22—C23	108.81 (10)
C6—C7—C8	110.10 (10)	C17—C22—H22A	108.0
C6—C7—H7A	109.6	C24—C22—H22A	108.0
C8—C7—H7A	109.6	C23—C22—H22A	108.0
C6—C7—H7B	109.6	C22—C23—H23A	109.5
C8—C7—H7B	109.6	C22—C23—H23B	109.5
H7A—C7—H7B	108.2	H23A—C23—H23B	109.5
C7—C8—C9	111.79 (10)	C22—C23—H23C	109.5
C7—C8—H8A	109.3	H23A—C23—H23C	109.5
C9—C8—H8A	109.3	H23B—C23—H23C	109.5
C7—C8—H8B	109.3	C22—C24—H24A	109.5
C9—C8—H8B	109.3	C22—C24—H24B	109.5
H8A—C8—H8B	107.9	H24A—C24—H24B	109.5
C8—C9—C2	113.24 (10)	C22—C24—H24C	109.5
C8—C9—H9A	108.9	H24A—C24—H24C	109.5
C2—C9—H9A	108.9	H24B—C24—H24C	109.5
C8—C9—H9B	108.9	C21—C25—C26	111.94 (10)
C2—C9—H9B	108.9	C21—C25—C27	111.11 (10)
H9A—C9—H9B	107.7	C26—C25—C27	109.66 (11)
C4—C10—H10A	109.5	C21—C25—H25A	108.0
C4—C10—H10B	109.5	C26—C25—H25A	108.0
H10A—C10—H10B	109.5	C27—C25—H25A	108.0
C4—C10—H10C	109.5	C25—C26—H26A	109.5
H10A—C10—H10C	109.5	C25—C26—H26B	109.5
H10B—C10—H10C	109.5	H26A—C26—H26B	109.5
C4—C11—H11A	109.5	C25—C26—H26C	109.5
C4—C11—H11B	109.5	H26A—C26—H26C	109.5
H11A—C11—H11B	109.5	H26B—C26—H26C	109.5
C4—C11—H11C	109.5	C25—C27—H27A	109.5
H11A—C11—H11C	109.5	C25—C27—H27B	109.5
H11B—C11—H11C	109.5	H27A—C27—H27B	109.5
N2—C12—C13	112.38 (10)	C25—C27—H27C	109.5
N2—C12—H12A	109.1	H27A—C27—H27C	109.5
C13—C12—H12A	109.1	H27B—C27—H27C	109.5
C14—N2—C1—N1	−44.13 (14)	C3—C2—C9—C8	−69.22 (13)
C12—N2—C1—N1	89.84 (12)	C5—C2—C9—C8	53.96 (13)
C14—N2—C1—C2	81.21 (13)	C1—C2—C9—C8	173.39 (10)
C12—N2—C1—C2	−144.82 (10)	C14—N2—C12—C13	−132.20 (11)
C16—N1—C1—N2	−82.53 (12)	C1—N2—C12—C13	91.09 (13)
C4—N1—C1—N2	129.41 (10)	C1—N2—C14—C15	−145.42 (11)
C16—N1—C1—C2	147.71 (10)	C12—N2—C14—C15	79.99 (13)
C4—N1—C1—C2	−0.35 (12)	C1—N1—C16—C21	118.88 (11)
N2—C1—C2—C3	−146.18 (10)	C4—N1—C16—C21	−96.14 (13)
N1—C1—C2—C3	−15.85 (11)	C1—N1—C16—C17	−59.47 (14)
N2—C1—C2—C9	−23.88 (14)	C4—N1—C16—C17	85.51 (14)
N1—C1—C2—C9	106.45 (11)	C21—C16—C17—C18	−2.55 (16)
N2—C1—C2—C5	95.48 (11)	N1—C16—C17—C18	175.80 (10)
N1—C1—C2—C5	−134.18 (10)	C21—C16—C17—C22	176.45 (10)
C9—C2—C3—C4	−97.89 (11)	N1—C16—C17—C22	−5.21 (17)
C5—C2—C3—C4	141.50 (10)	C16—C17—C18—C19	1.60 (18)
C1—C2—C3—C4	26.27 (12)	C22—C17—C18—C19	−177.46 (11)
C16—N1—C4—C11	−10.30 (15)	C17—C18—C19—C20	0.55 (19)
C1—N1—C4—C11	136.35 (10)	C18—C19—C20—C21	−1.75 (19)
C16—N1—C4—C3	−130.19 (11)	C19—C20—C21—C16	0.76 (18)
C1—N1—C4—C3	16.45 (12)	C19—C20—C21—C25	−179.70 (11)
C16—N1—C4—C10	110.60 (12)	C17—C16—C21—C20	1.40 (16)
C1—N1—C4—C10	−102.76 (11)	N1—C16—C21—C20	−177.00 (10)
C2—C3—C4—N1	−26.48 (12)	C17—C16—C21—C25	−178.12 (10)
C2—C3—C4—C11	−147.79 (10)	N1—C16—C21—C25	3.48 (16)
C2—C3—C4—C10	92.57 (11)	C18—C17—C22—C24	54.13 (14)
C3—C2—C5—C6	68.34 (13)	C16—C17—C22—C24	−124.88 (12)
C9—C2—C5—C6	−54.98 (13)	C18—C17—C22—C23	−68.32 (14)
C1—C2—C5—C6	−179.06 (9)	C16—C17—C22—C23	112.66 (13)
C2—C5—C6—C7	57.69 (13)	C20—C21—C25—C26	52.45 (15)
C5—C6—C7—C8	−55.75 (13)	C16—C21—C25—C26	−128.02 (12)
C6—C7—C8—C9	55.59 (13)	C20—C21—C25—C27	−70.53 (14)
C7—C8—C9—C2	−56.42 (13)	C16—C21—C25—C27	109.01 (13)