(3R,5S,6R,8S,9S)-1-Azonia-9-ethyl-3-hydr­oxy-5-(6-meth­oxyquinolin-4-yl)-3-methyl-4-oxatricyclo­[6.2.2.0]dodecane trifluoro­methane­sulfonate: insight into the sterochemistry of the cyclization mechanism

The analysis of the crystal structure of the title compound, C₂₃H₃₁N₂O₃⁺·CF₃SO₃⁻, allowed the determination of the relative configuration at the five stereogenic centres.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.124
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S30
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C34
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O26    -   H521   ...       0.67 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           75.03
           From the CIF: _reflns_number_total               2794
           Count of symmetry unique reflns         2794
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

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

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

---

Computing details

Data collection: CAD4/Mach3 (Enraf–Nonius, 2000); cell refinement: CAD4/Mach3; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

11S,13R,16R,18S,22S-1-Azonia-9-ethyl-3- hydroxy-5-(6-methoxy-quinolin-4-yl)-3-methyl- 4-oxatricyclo[6.2.2.0]dodecane trifluoromethanesulfonate

Crystal data

C23H31N2O3^+·CF3SO3^−	F(000) = 560
Mr = 532.57	Dx = 1.407 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 11.312 (1) Å	θ = 20–35°
b = 8.059 (1) Å	µ = 1.72 mm^−1
c = 14.074 (1) Å	T = 293 K
β = 101.49 (1)°	Prism, colorless
V = 1257.3 (2) Å^3	0.50 × 0.35 × 0.20 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	2634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 75.0°, θmin = 3.2°
ω/2θ scans	h = −14→13
Absorption correction: analytical de Meulenaer & Tompa 1965	k = 0→10
Tmin = 0.480, Tmax = 0.725	l = 0→17
2906 measured reflections	3 standard reflections every 60 reflections
2794 independent reflections	intensity decay: 1.5%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.082P)^2 + 0.328P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.124	(Δ/σ)max = 0.002
S = 0.99	Δρmax = 0.33 e Å^−3
2794 reflections	Δρmin = −0.34 e Å^−3
333 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0263 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: not refined (see text)
Secondary atom site location: difference Fourier map

Special details

Experimental. No Friedel related reflections were measured in the present data collection. Thus Flack test results are meaningless.

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
O12	0.21910 (17)	0.2748 (3)	0.82739 (13)	0.0369 (5)
O26	0.3721 (2)	0.1585 (3)	0.94418 (19)	0.0478 (6)
O27	0.5594 (4)	0.0800 (7)	0.5116 (3)	0.1006 (14)
N1	0.0675 (4)	0.1236 (6)	0.4824 (2)	0.0748 (11)
N15	0.3358 (2)	0.5614 (3)	0.84133 (15)	0.0353 (5)
C2	0.0215 (4)	0.1758 (6)	0.5551 (3)	0.0699 (11)
H2	−0.0621	0.1786	0.5472	0.084*
C3	0.0906 (3)	0.2283 (5)	0.6448 (2)	0.0536 (8)
H3	0.0525	0.2637	0.6940	0.064*
C4	0.2131 (3)	0.2268 (4)	0.6589 (2)	0.0425 (7)
C5	0.2687 (3)	0.1713 (4)	0.5829 (2)	0.0471 (7)
C6	0.3950 (4)	0.1594 (5)	0.5900 (2)	0.0538 (8)
H6	0.4473	0.1904	0.6468	0.065*
C7	0.4396 (5)	0.1021 (7)	0.5127 (3)	0.0714 (12)
C8	0.3613 (7)	0.0602 (9)	0.4249 (3)	0.0916 (18)
H8	0.3932	0.0264	0.3720	0.110*
C9	0.2418 (6)	0.0687 (8)	0.4170 (3)	0.0897 (17)
H9	0.1917	0.0382	0.3589	0.108*
C10	0.1895 (4)	0.1233 (5)	0.4955 (2)	0.0617 (10)
C11	0.2883 (2)	0.2888 (4)	0.75318 (18)	0.0348 (6)
H11	0.3603	0.2189	0.7704	0.042*
C13	0.2935 (2)	0.2931 (5)	0.92227 (18)	0.0377 (6)
C14	0.3772 (3)	0.4427 (4)	0.9231 (2)	0.0378 (6)
H14A	0.3831	0.5014	0.9840	0.045*
H14B	0.4572	0.4032	0.9196	0.045*
C16	0.3286 (3)	0.4716 (4)	0.7442 (2)	0.0370 (6)
H16	0.4106	0.4682	0.7315	0.044*
C17	0.2535 (3)	0.5820 (4)	0.6658 (2)	0.0472 (7)
H17A	0.2819	0.5703	0.6055	0.057*
H17B	0.1694	0.5487	0.6545	0.057*
C18	0.2661 (4)	0.7635 (4)	0.7001 (2)	0.0525 (8)
H18	0.2402	0.8392	0.6454	0.063*
C19	0.3977 (3)	0.7963 (5)	0.7481 (3)	0.0579 (8)
H19A	0.4506	0.7602	0.7056	0.070*
H19B	0.4102	0.9141	0.7601	0.070*
C20	0.4269 (3)	0.7001 (4)	0.8444 (2)	0.0472 (7)
H20A	0.5077	0.6544	0.8537	0.057*
H20B	0.4232	0.7741	0.8981	0.057*
C21	0.2153 (3)	0.6401 (4)	0.8470 (2)	0.0393 (6)
H21A	0.2165	0.6763	0.9129	0.047*
H21B	0.1516	0.5585	0.8297	0.047*
C22	0.1895 (3)	0.7893 (5)	0.7779 (2)	0.0495 (7)
H22	0.2178	0.8900	0.8145	0.059*
C23	0.0537 (3)	0.8058 (6)	0.7391 (3)	0.0649 (10)
H23A	0.0398	0.8928	0.6905	0.078*
H23B	0.0236	0.7027	0.7077	0.078*
C24	−0.0164 (4)	0.8453 (8)	0.8169 (4)	0.0867 (16)
H24A	−0.0049	0.7582	0.8644	0.130*
H24B	−0.1006	0.8546	0.7884	0.130*
H24C	0.0118	0.9483	0.8475	0.130*
C25	0.2069 (3)	0.3051 (6)	0.9916 (2)	0.0491 (7)
H25A	0.1608	0.2045	0.9887	0.074*
H25B	0.1534	0.3973	0.9737	0.074*
H25C	0.2517	0.3209	1.0565	0.074*
C28	0.6427 (5)	0.0852 (12)	0.6014 (4)	0.105 (2)
H28A	0.6581	0.1985	0.6210	0.157*
H28B	0.7168	0.0331	0.5944	0.157*
H28C	0.6096	0.0273	0.6497	0.157*
S30	0.31245 (7)	0.80895 (14)	0.13237 (5)	0.0534 (3)
F35	0.1106 (4)	0.9532 (7)	0.1371 (5)	0.158 (2)
F36	0.1449 (3)	0.7475 (6)	0.2302 (2)	0.1063 (13)
F37	0.0925 (3)	0.7108 (6)	0.0777 (2)	0.1042 (12)
O31	0.3725 (3)	0.9052 (8)	0.2093 (2)	0.1173 (19)
O32	0.3450 (4)	0.6351 (6)	0.1408 (3)	0.1025 (14)
O33	0.3076 (3)	0.8745 (4)	0.03761 (17)	0.0626 (7)
C34	0.1578 (3)	0.8033 (7)	0.1460 (3)	0.0688 (11)
H521	0.348 (4)	0.102 (8)	0.970 (4)	0.069 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O12	0.0405 (9)	0.0406 (11)	0.0297 (9)	−0.0029 (8)	0.0073 (7)	−0.0001 (8)
O26	0.0478 (12)	0.0496 (14)	0.0463 (13)	0.0059 (11)	0.0102 (10)	0.0143 (11)
O27	0.111 (3)	0.130 (4)	0.077 (2)	−0.009 (3)	0.056 (2)	−0.039 (2)
N1	0.094 (3)	0.076 (3)	0.0446 (16)	−0.012 (2)	−0.0115 (16)	−0.0061 (17)
N15	0.0414 (11)	0.0332 (12)	0.0316 (11)	−0.0031 (10)	0.0081 (9)	−0.0043 (10)
C2	0.070 (2)	0.076 (3)	0.053 (2)	−0.010 (2)	−0.0107 (17)	0.003 (2)
C3	0.0585 (18)	0.056 (2)	0.0437 (16)	−0.0059 (17)	0.0030 (14)	−0.0042 (16)
C4	0.0617 (18)	0.0326 (14)	0.0315 (13)	−0.0041 (14)	0.0053 (12)	−0.0021 (12)
C5	0.079 (2)	0.0313 (15)	0.0321 (13)	−0.0060 (15)	0.0120 (13)	−0.0035 (12)
C6	0.080 (2)	0.0485 (19)	0.0363 (15)	−0.0073 (18)	0.0199 (15)	−0.0081 (14)
C7	0.100 (3)	0.070 (3)	0.052 (2)	−0.006 (2)	0.035 (2)	−0.016 (2)
C8	0.131 (5)	0.103 (4)	0.046 (2)	0.001 (4)	0.033 (3)	−0.026 (3)
C9	0.137 (5)	0.093 (4)	0.0362 (18)	−0.008 (4)	0.009 (2)	−0.030 (2)
C10	0.094 (3)	0.052 (2)	0.0355 (16)	−0.008 (2)	0.0051 (16)	−0.0054 (15)
C11	0.0445 (13)	0.0322 (13)	0.0286 (11)	−0.0003 (12)	0.0095 (10)	−0.0035 (11)
C13	0.0391 (12)	0.0455 (15)	0.0292 (11)	0.0014 (14)	0.0083 (9)	0.0026 (12)
C14	0.0385 (13)	0.0432 (16)	0.0307 (13)	0.0028 (12)	0.0045 (10)	−0.0017 (12)
C16	0.0478 (14)	0.0352 (15)	0.0300 (12)	−0.0020 (12)	0.0129 (11)	−0.0053 (11)
C17	0.069 (2)	0.0411 (16)	0.0322 (14)	−0.0018 (15)	0.0126 (13)	0.0010 (13)
C18	0.074 (2)	0.0400 (19)	0.0421 (16)	−0.0046 (15)	0.0089 (15)	0.0057 (13)
C19	0.073 (2)	0.0411 (17)	0.063 (2)	−0.0148 (19)	0.0221 (16)	0.0011 (18)
C20	0.0500 (16)	0.0411 (17)	0.0502 (16)	−0.0098 (14)	0.0094 (13)	−0.0081 (14)
C21	0.0446 (14)	0.0357 (15)	0.0375 (14)	0.0038 (12)	0.0076 (11)	−0.0059 (12)
C22	0.0617 (17)	0.0358 (15)	0.0475 (16)	0.0018 (16)	0.0024 (13)	−0.0050 (15)
C23	0.067 (2)	0.050 (2)	0.070 (2)	0.010 (2)	−0.0037 (17)	0.005 (2)
C24	0.066 (2)	0.081 (4)	0.112 (4)	0.026 (2)	0.014 (2)	−0.012 (3)
C25	0.0486 (14)	0.066 (2)	0.0364 (13)	−0.0009 (18)	0.0164 (11)	0.0050 (17)
C28	0.082 (3)	0.148 (6)	0.095 (4)	0.000 (4)	0.044 (3)	−0.031 (4)
S30	0.0501 (4)	0.0753 (6)	0.0377 (4)	−0.0155 (4)	0.0159 (3)	−0.0061 (4)
F35	0.143 (4)	0.114 (3)	0.242 (6)	0.058 (3)	0.102 (4)	0.030 (4)
F36	0.0935 (17)	0.155 (4)	0.0880 (18)	−0.036 (2)	0.0588 (15)	−0.005 (2)
F37	0.0631 (14)	0.148 (3)	0.097 (2)	−0.0435 (18)	0.0043 (13)	−0.006 (2)
O31	0.107 (2)	0.198 (5)	0.0515 (16)	−0.089 (3)	0.0272 (16)	−0.038 (2)
O32	0.116 (3)	0.092 (3)	0.111 (3)	0.035 (3)	0.051 (2)	0.030 (3)
O33	0.0776 (16)	0.0665 (17)	0.0467 (13)	−0.0201 (14)	0.0200 (11)	−0.0018 (12)
C34	0.0549 (18)	0.077 (3)	0.080 (3)	−0.011 (2)	0.0277 (18)	−0.009 (3)

Geometric parameters (Å, º)

O12—C11	1.429 (3)	C17—C18	1.538 (5)
O12—C13	1.437 (3)	C17—H17A	0.9700
O26—C13	1.398 (4)	C17—H17B	0.9700
O26—H521	0.67 (6)	C18—C22	1.540 (5)
O27—C7	1.370 (6)	C18—C19	1.530 (5)
O27—C28	1.419 (7)	C18—H18	0.9800
N1—C2	1.306 (6)	C19—C20	1.539 (5)
N1—C10	1.356 (6)	C19—H19A	0.9700
N15—C14	1.498 (4)	C19—H19B	0.9700
N15—C21	1.519 (4)	C20—H20A	0.9700
N15—C20	1.515 (4)	C20—H20B	0.9700
N15—C16	1.534 (3)	C21—C22	1.537 (5)
C2—C3	1.411 (5)	C21—H21A	0.9700
C2—H2	0.9300	C21—H21B	0.9700
C3—C4	1.360 (5)	C22—C23	1.531 (5)
C3—H3	0.9300	C22—H22	0.9800
C4—C5	1.418 (4)	C23—C24	1.509 (7)
C4—C11	1.511 (4)	C23—H23A	0.9700
C5—C6	1.415 (5)	C23—H23B	0.9700
C5—C10	1.423 (5)	C24—H24A	0.9600
C6—C7	1.368 (5)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C7—C8	1.410 (7)	C25—H25A	0.9600
C8—C9	1.336 (9)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C10	1.424 (6)	C28—H28A	0.9600
C9—H9	0.9300	C28—H28B	0.9600
C11—C16	1.555 (4)	C28—H28C	0.9600
C11—H11	0.9800	S30—O31	1.393 (4)
C13—C25	1.518 (4)	S30—O33	1.425 (3)
C13—C14	1.531 (5)	S30—O32	1.447 (5)
C14—H14A	0.9700	S30—C34	1.798 (4)
C14—H14B	0.9700	F35—C34	1.317 (8)
C16—C17	1.536 (4)	F36—C34	1.302 (5)
C16—H16	0.9800	F37—C34	1.320 (6)
C11—O12—C13	111.48 (19)	C22—C18—C19	107.4 (3)
C13—O26—H521	110 (5)	C22—C18—C17	108.7 (3)
C7—O27—C28	118.0 (3)	C19—C18—C17	108.9 (3)
C2—N1—C10	116.6 (3)	C22—C18—H18	110.6
C14—N15—C21	111.9 (2)	C19—C18—H18	110.6
C14—N15—C20	110.0 (2)	C17—C18—H18	110.6
C21—N15—C20	107.6 (2)	C20—C19—C18	108.7 (3)
C14—N15—C16	109.6 (2)	C20—C19—H19A	109.9
C21—N15—C16	110.7 (2)	C18—C19—H19A	109.9
C20—N15—C16	106.8 (2)	C20—C19—H19B	109.9
N1—C2—C3	124.1 (4)	C18—C19—H19B	109.9
N1—C2—H2	117.9	H19A—C19—H19B	108.3
C3—C2—H2	117.9	N15—C20—C19	108.7 (2)
C4—C3—C2	119.6 (4)	N15—C20—H20A	109.9
C4—C3—H3	120.2	C19—C20—H20A	109.9
C2—C3—H3	120.2	N15—C20—H20B	109.9
C3—C4—C5	119.0 (3)	C19—C20—H20B	109.9
C3—C4—C11	120.3 (3)	H20A—C20—H20B	108.3
C5—C4—C11	120.6 (3)	N15—C21—C22	110.7 (2)
C6—C5—C4	124.2 (3)	N15—C21—H21A	109.5
C6—C5—C10	119.7 (3)	C22—C21—H21A	109.5
C4—C5—C10	116.1 (3)	N15—C21—H21B	109.5
C7—C6—C5	119.6 (4)	C22—C21—H21B	109.5
C7—C6—H6	120.2	H21A—C21—H21B	108.1
C5—C6—H6	120.2	C18—C22—C23	115.1 (3)
O27—C7—C6	125.2 (4)	C18—C22—C21	106.3 (3)
O27—C7—C8	114.2 (4)	C23—C22—C21	110.1 (3)
C6—C7—C8	120.7 (5)	C18—C22—H22	108.4
C9—C8—C7	120.7 (4)	C23—C22—H22	108.4
C9—C8—H8	119.7	C21—C22—H22	108.4
C7—C8—H8	119.7	C24—C23—C22	113.2 (3)
C8—C9—C10	121.4 (4)	C24—C23—H23A	108.9
C8—C9—H9	119.3	C22—C23—H23A	108.9
C10—C9—H9	119.3	C24—C23—H23B	108.9
N1—C10—C5	124.5 (4)	C22—C23—H23B	108.9
N1—C10—C9	117.6 (4)	H23A—C23—H23B	107.7
C5—C10—C9	117.8 (4)	C23—C24—H24A	109.5
O12—C11—C4	108.7 (2)	C23—C24—H24B	109.5
O12—C11—C16	110.2 (2)	H24A—C24—H24B	109.5
C4—C11—C16	111.4 (2)	C23—C24—H24C	109.5
O12—C11—H11	108.8	H24A—C24—H24C	109.5
C4—C11—H11	108.8	H24B—C24—H24C	109.5
C16—C11—H11	108.8	C13—C25—H25A	109.5
O26—C13—O12	110.8 (3)	C13—C25—H25B	109.5
O26—C13—C25	111.8 (3)	H25A—C25—H25B	109.5
O12—C13—C25	105.7 (2)	C13—C25—H25C	109.5
O26—C13—C14	104.2 (2)	H25A—C25—H25C	109.5
O12—C13—C14	109.5 (2)	H25B—C25—H25C	109.5
C25—C13—C14	115.0 (3)	O27—C28—H28A	109.5
N15—C14—C13	113.5 (2)	O27—C28—H28B	109.5
N15—C14—H14A	108.9	H28A—C28—H28B	109.5
C13—C14—H14A	108.9	O27—C28—H28C	109.5
N15—C14—H14B	108.9	H28A—C28—H28C	109.5
C13—C14—H14B	108.9	H28B—C28—H28C	109.5
H14A—C14—H14B	107.7	O31—S30—O33	116.3 (2)
N15—C16—C17	106.9 (2)	O31—S30—O32	113.5 (3)
N15—C16—C11	109.9 (2)	O33—S30—O32	113.4 (2)
C17—C16—C11	118.6 (2)	O31—S30—C34	105.4 (2)
N15—C16—H16	107.0	O33—S30—C34	104.6 (2)
C17—C16—H16	107.0	O32—S30—C34	101.8 (3)
C11—C16—H16	107.0	F36—C34—F35	106.7 (5)
C18—C17—C16	108.8 (3)	F36—C34—F37	108.6 (4)
C18—C17—H17A	109.9	F35—C34—F37	106.9 (5)
C16—C17—H17A	109.9	F36—C34—S30	113.2 (3)
C18—C17—H17B	109.9	F35—C34—S30	110.6 (4)
C16—C17—H17B	109.9	F37—C34—S30	110.6 (3)
H17A—C17—H17B	108.3
C10—N1—C2—C3	−1.0 (7)	C14—N15—C16—C17	164.4 (2)
N1—C2—C3—C4	0.3 (7)	C21—N15—C16—C17	40.5 (3)
C2—C3—C4—C5	−0.4 (6)	C20—N15—C16—C17	−76.4 (3)
C2—C3—C4—C11	177.7 (4)	C14—N15—C16—C11	34.5 (3)
C3—C4—C5—C6	−178.0 (4)	C21—N15—C16—C11	−89.4 (3)
C11—C4—C5—C6	3.9 (5)	C20—N15—C16—C11	153.7 (2)
C3—C4—C5—C10	1.0 (5)	O12—C11—C16—N15	26.3 (3)
C11—C4—C5—C10	−177.0 (3)	C4—C11—C16—N15	147.0 (2)
C4—C5—C6—C7	179.1 (4)	O12—C11—C16—C17	−97.0 (3)
C10—C5—C6—C7	0.1 (6)	C4—C11—C16—C17	23.7 (3)
C28—O27—C7—C6	13.0 (9)	N15—C16—C17—C18	27.0 (3)
C28—O27—C7—C8	−167.0 (7)	C11—C16—C17—C18	151.7 (3)
C5—C6—C7—O27	−177.8 (5)	C16—C17—C18—C22	−75.3 (4)
C5—C6—C7—C8	2.2 (8)	C16—C17—C18—C19	41.4 (4)
O27—C7—C8—C9	177.0 (6)	C22—C18—C19—C20	48.2 (4)
C6—C7—C8—C9	−3.0 (10)	C17—C18—C19—C20	−69.3 (4)
C7—C8—C9—C10	1.4 (10)	C14—N15—C20—C19	167.1 (3)
C2—N1—C10—C5	1.8 (7)	C21—N15—C20—C19	−70.7 (3)
C2—N1—C10—C9	−179.3 (5)	C16—N15—C20—C19	48.3 (3)
C6—C5—C10—N1	177.3 (4)	C18—C19—C20—N15	20.6 (4)
C4—C5—C10—N1	−1.8 (6)	C14—N15—C21—C22	166.6 (2)
C6—C5—C10—C9	−1.6 (6)	C20—N15—C21—C22	45.6 (3)
C4—C5—C10—C9	179.3 (4)	C16—N15—C21—C22	−70.7 (3)
C8—C9—C10—N1	−178.1 (6)	C19—C18—C22—C23	165.1 (3)
C8—C9—C10—C5	0.9 (8)	C17—C18—C22—C23	−77.2 (4)
C13—O12—C11—C4	166.0 (3)	C19—C18—C22—C21	−72.6 (3)
C13—O12—C11—C16	−71.6 (3)	C17—C18—C22—C21	45.1 (3)
C3—C4—C11—O12	24.3 (4)	N15—C21—C22—C18	22.4 (3)
C5—C4—C11—O12	−157.6 (3)	N15—C21—C22—C23	147.8 (3)
C3—C4—C11—C16	−97.3 (3)	C18—C22—C23—C24	−175.1 (4)
C5—C4—C11—C16	80.7 (3)	C21—C22—C23—C24	64.7 (5)
C11—O12—C13—O26	−68.1 (3)	O31—S30—C34—F36	−56.2 (5)
C11—O12—C13—C25	170.7 (3)	O33—S30—C34—F36	−179.3 (4)
C11—O12—C13—C14	46.2 (3)	O32—S30—C34—F36	62.4 (5)
C21—N15—C14—C13	63.5 (3)	O31—S30—C34—F35	63.4 (5)
C20—N15—C14—C13	−176.9 (2)	O33—S30—C34—F35	−59.7 (5)
C16—N15—C14—C13	−59.8 (3)	O32—S30—C34—F35	−177.9 (5)
O26—C13—C14—N15	137.5 (2)	O31—S30—C34—F37	−178.3 (4)
O12—C13—C14—N15	19.0 (3)	O33—S30—C34—F37	58.6 (4)
C25—C13—C14—N15	−99.8 (3)	O32—S30—C34—F37	−59.7 (5)