7β,14β-Epoxy­hydro­codone-6,6-di­methoxy ketal: an unusual oxetane-containing opioid

The title compound, C₂₀H₂₅NO₅, which was formed by reaction of 7α-bromo­hydro­codone-6,6-di­methoxy ketal with KO^tBu in tetra­hydro­furan, is the first example of a 7,14-bridged oxetane. The geometry of the oxetane ring is consistent with previously reported structures.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT773_ALERT_2_A Suspect C-C Bond in CIF    C7     -   C14      =       2.02 Ang.

Author Response: These atoms are not bonded but are members of an oxetane ring which has a normal geometry for such a ring, but is unusual when compared to more 'normal' structures.

Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
REFLT03_ALERT_1_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.36
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2063
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2181
           Completeness (_total/calc)             94.59%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.36
           From the CIF: _reflns_number_total               2063
           Count of symmetry unique reflns         2181
           Completeness (_total/calc)             94.59%
           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           no

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART and SAINT (Bruker, 2002); data reduction: SAINT and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(4)

Crystal data

C20H25NO5	Z = 1
Mr = 359.41	F(000) = 192
Triclinic, P1	Dx = 1.369 Mg m^−3
a = 7.509 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.777 (2) Å	Cell parameters from 3226 reflections
c = 8.430 (2) Å	θ = 2.6–28.3°
α = 83.776 (6)°	µ = 0.10 mm^−1
β = 68.993 (5)°	T = 103 K
γ = 71.511 (5)°	Irregular prism, colorless
V = 435.81 (19) Å^3	0.40 × 0.30 × 0.25 mm

Data collection

Bruker SMART 1000 CCD diffractometer	2063 independent reflections
Radiation source: sealed tube	2036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.962, Tmax = 0.976	k = −10→10
3770 measured reflections	l = −11→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.0944P] where P = (Fo^2 + 2Fc^2)/3
2063 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.34 e Å^−3
3 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
C1	0.2152 (3)	0.4085 (3)	0.5092 (2)	0.0221 (4)
H1A	0.2670	0.4890	0.4255	0.027*
C2	0.3019 (3)	0.2216 (3)	0.4836 (2)	0.0224 (4)
H2A	0.4036	0.1777	0.3783	0.027*
C3	0.2429 (3)	0.0972 (3)	0.6088 (2)	0.0189 (3)
O3A	0.3297 (2)	−0.08633 (19)	0.60108 (18)	0.0238 (3)
C3A	0.4927 (3)	−0.1581 (3)	0.4483 (3)	0.0305 (5)
H3AA	0.5357	−0.2908	0.4535	0.046*
H3AB	0.6045	−0.1129	0.4370	0.046*
H3AC	0.4491	−0.1196	0.3501	0.046*
C4	0.0850 (2)	0.1698 (2)	0.7569 (2)	0.0159 (3)
O3	0.03019 (19)	0.07758 (17)	0.90728 (16)	0.0170 (3)
C5	−0.1221 (2)	0.2095 (2)	1.0358 (2)	0.0143 (3)
H5A	−0.2468	0.1720	1.0772	0.017*
C6	−0.0625 (3)	0.2214 (2)	1.1934 (2)	0.0156 (3)
O6A	0.1121 (2)	0.08793 (18)	1.19864 (17)	0.0204 (3)
C6A	0.0975 (3)	−0.0932 (3)	1.2269 (3)	0.0263 (4)
H6AA	0.2318	−0.1798	1.1995	0.039*
H6AB	0.0312	−0.1170	1.1541	0.039*
H6AC	0.0194	−0.1065	1.3463	0.039*
O6B	−0.23515 (19)	0.20892 (18)	1.33069 (16)	0.0193 (3)
C6B	−0.2444 (3)	0.2531 (3)	1.4944 (2)	0.0256 (4)
H6BA	−0.3537	0.2180	1.5825	0.038*
H6BB	−0.2683	0.3839	1.5016	0.038*
H6BC	−0.1176	0.1876	1.5113	0.038*
C7	−0.0219 (3)	0.4024 (2)	1.1979 (2)	0.0174 (3)
H7A	0.0263	0.4129	1.2916	0.021*
O7	−0.19684 (19)	0.55205 (17)	1.19093 (16)	0.0182 (3)
C8	0.1023 (3)	0.4544 (2)	1.0224 (2)	0.0170 (3)
H8A	0.1914	0.3509	0.9451	0.020*
H8B	0.1718	0.5430	1.0236	0.020*
C9	−0.1515 (3)	0.7110 (2)	0.9043 (2)	0.0174 (3)
H9A	−0.1143	0.8047	0.9472	0.021*
C10	−0.0212 (3)	0.6765 (2)	0.7115 (2)	0.0210 (4)
H10A	−0.1013	0.7486	0.6425	0.025*
H10B	0.0957	0.7211	0.6870	0.025*
C11	0.0537 (3)	0.4791 (2)	0.6558 (2)	0.0179 (3)
C12	−0.0173 (3)	0.3519 (2)	0.7694 (2)	0.0152 (3)
C13	−0.1669 (2)	0.3951 (2)	0.9449 (2)	0.0134 (3)
C14	−0.1057 (2)	0.5382 (2)	1.0055 (2)	0.0154 (3)
C15	−0.3874 (3)	0.4662 (2)	0.9584 (2)	0.0168 (3)
H15A	−0.4186	0.3779	0.9044	0.020*
H15B	−0.4731	0.4772	1.0798	0.020*
C16	−0.4350 (3)	0.6492 (2)	0.8736 (2)	0.0193 (3)
H16A	−0.3657	0.6357	0.7491	0.023*
H16B	−0.5807	0.6973	0.8960	0.023*
N17	−0.3696 (2)	0.7754 (2)	0.9403 (2)	0.0194 (3)
C17	−0.4354 (3)	0.9591 (3)	0.8775 (3)	0.0268 (4)
H17C	−0.5818	1.0015	0.9155	0.040*
H17D	−0.3809	0.9584	0.7530	0.040*
H17A	−0.3875	1.0404	0.9219	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0201 (8)	0.0300 (10)	0.0154 (8)	−0.0095 (8)	−0.0042 (7)	0.0028 (7)
C2	0.0158 (8)	0.0341 (11)	0.0145 (8)	−0.0060 (8)	−0.0025 (6)	−0.0030 (7)
C3	0.0149 (8)	0.0236 (9)	0.0176 (8)	−0.0039 (7)	−0.0051 (6)	−0.0052 (7)
O3A	0.0185 (6)	0.0237 (7)	0.0222 (7)	−0.0004 (5)	−0.0016 (5)	−0.0091 (5)
C3A	0.0213 (9)	0.0349 (11)	0.0253 (10)	0.0022 (8)	−0.0018 (8)	−0.0136 (8)
C4	0.0139 (8)	0.0192 (8)	0.0155 (8)	−0.0057 (6)	−0.0050 (6)	−0.0014 (6)
O3	0.0183 (6)	0.0145 (6)	0.0144 (6)	−0.0020 (5)	−0.0027 (5)	−0.0031 (5)
C5	0.0131 (7)	0.0142 (7)	0.0142 (7)	−0.0027 (6)	−0.0038 (6)	−0.0014 (6)
C6	0.0147 (8)	0.0162 (8)	0.0144 (7)	−0.0028 (6)	−0.0044 (6)	−0.0009 (6)
O6A	0.0183 (6)	0.0195 (6)	0.0237 (6)	−0.0019 (5)	−0.0105 (5)	−0.0008 (5)
C6A	0.0305 (10)	0.0188 (9)	0.0286 (10)	−0.0021 (8)	−0.0143 (8)	0.0025 (7)
O6B	0.0191 (6)	0.0253 (7)	0.0128 (6)	−0.0077 (5)	−0.0036 (5)	0.0000 (5)
C6B	0.0279 (10)	0.0335 (11)	0.0147 (8)	−0.0087 (8)	−0.0065 (7)	−0.0013 (7)
C7	0.0180 (8)	0.0187 (8)	0.0171 (8)	−0.0041 (7)	−0.0080 (6)	−0.0032 (6)
O7	0.0191 (6)	0.0176 (6)	0.0163 (6)	−0.0023 (5)	−0.0061 (5)	−0.0035 (5)
C8	0.0157 (8)	0.0168 (8)	0.0209 (8)	−0.0065 (6)	−0.0075 (6)	−0.0003 (6)
C9	0.0175 (8)	0.0135 (8)	0.0225 (9)	−0.0052 (6)	−0.0080 (7)	0.0004 (6)
C10	0.0183 (8)	0.0190 (9)	0.0228 (9)	−0.0062 (7)	−0.0041 (7)	0.0033 (7)
C11	0.0145 (8)	0.0223 (9)	0.0170 (8)	−0.0060 (7)	−0.0054 (6)	0.0017 (7)
C12	0.0118 (7)	0.0200 (8)	0.0130 (7)	−0.0041 (6)	−0.0032 (6)	−0.0023 (6)
C13	0.0122 (7)	0.0134 (8)	0.0142 (7)	−0.0038 (6)	−0.0038 (6)	−0.0009 (6)
C14	0.0139 (7)	0.0149 (8)	0.0168 (8)	−0.0038 (6)	−0.0047 (6)	−0.0015 (6)
C15	0.0126 (7)	0.0178 (8)	0.0196 (8)	−0.0044 (6)	−0.0048 (6)	−0.0005 (6)
C16	0.0159 (8)	0.0177 (8)	0.0248 (9)	−0.0039 (6)	−0.0087 (6)	0.0008 (7)
N17	0.0163 (7)	0.0143 (7)	0.0274 (8)	−0.0029 (6)	−0.0084 (6)	−0.0005 (6)
C17	0.0255 (10)	0.0164 (9)	0.0388 (11)	−0.0036 (7)	−0.0146 (9)	0.0032 (8)

Geometric parameters (Å, º)

C1—C2	1.396 (3)	C7—C8	1.530 (2)
C1—C11	1.396 (2)	C7—C14	2.020 (3)
C1—H1A	0.9500	C7—H7A	1.0000
C2—C3	1.401 (3)	O7—C14	1.465 (2)
C2—H2A	0.9500	C8—C14	1.542 (2)
C3—O3A	1.366 (2)	C8—H8A	0.9900
C3—C4	1.397 (2)	C8—H8B	0.9900
O3A—C3A	1.436 (2)	C9—N17	1.477 (2)
C3A—H3AA	0.9800	C9—C14	1.523 (2)
C3A—H3AB	0.9800	C9—C10	1.568 (3)
C3A—H3AC	0.9800	C9—H9A	1.0000
C4—C12	1.375 (2)	C10—C11	1.520 (3)
C4—O3	1.381 (2)	C10—H10A	0.9900
O3—C5	1.464 (2)	C10—H10B	0.9900
C5—C13	1.555 (2)	C11—C12	1.394 (2)
C5—C6	1.566 (2)	C12—C13	1.497 (2)
C5—H5A	1.0000	C13—C14	1.526 (2)
C6—O6A	1.403 (2)	C13—C15	1.535 (2)
C6—O6B	1.417 (2)	C15—C16	1.518 (2)
C6—C7	1.539 (2)	C15—H15A	0.9900
O6A—C6A	1.435 (2)	C15—H15B	0.9900
C6A—H6AA	0.9800	C16—N17	1.464 (2)
C6A—H6AB	0.9800	C16—H16A	0.9900
C6A—H6AC	0.9800	C16—H16B	0.9900
O6B—C6B	1.431 (2)	N17—C17	1.463 (2)
C6B—H6BA	0.9800	C17—H17C	0.9800
C6B—H6BB	0.9800	C17—H17D	0.9800
C6B—H6BC	0.9800	C17—H17A	0.9800
C7—O7	1.468 (2)
C2—C1—C11	121.10 (17)	C14—C8—H8A	114.9
C2—C1—H1A	119.5	C7—C8—H8B	114.9
C11—C1—H1A	119.4	C14—C8—H8B	114.9
C1—C2—C3	121.83 (17)	H8A—C8—H8B	112.0
C1—C2—H2A	119.1	N17—C9—C14	107.77 (14)
C3—C2—H2A	119.1	N17—C9—C10	114.81 (15)
O3A—C3—C4	117.60 (16)	C14—C9—C10	110.23 (14)
O3A—C3—C2	126.01 (16)	N17—C9—H9A	107.9
C4—C3—C2	116.35 (17)	C14—C9—H9A	107.9
C3—O3A—C3A	116.75 (16)	C10—C9—H9A	107.9
O3A—C3A—H3AA	109.5	C11—C10—C9	114.60 (15)
O3A—C3A—H3AB	109.5	C11—C10—H10A	108.6
H3AA—C3A—H3AB	109.5	C9—C10—H10A	108.6
O3A—C3A—H3AC	109.5	C11—C10—H10B	108.6
H3AA—C3A—H3AC	109.5	C9—C10—H10B	108.6
H3AB—C3A—H3AC	109.5	H10A—C10—H10B	107.6
C12—C4—O3	113.41 (15)	C12—C11—C1	115.77 (17)
C12—C4—C3	120.72 (16)	C12—C11—C10	118.96 (16)
O3—C4—C3	125.48 (16)	C1—C11—C10	124.31 (17)
C4—O3—C5	107.61 (13)	C4—C12—C11	122.76 (16)
O3—C5—C13	107.11 (13)	C4—C12—C13	109.56 (15)
O3—C5—C6	113.73 (14)	C11—C12—C13	124.65 (16)
C13—C5—C6	112.29 (13)	C12—C13—C14	102.68 (13)
O3—C5—H5A	107.8	C12—C13—C15	116.06 (14)
C13—C5—H5A	107.8	C14—C13—C15	110.78 (14)
C6—C5—H5A	107.8	C12—C13—C5	102.08 (14)
O6A—C6—O6B	112.74 (14)	C14—C13—C5	113.60 (14)
O6A—C6—C7	104.74 (14)	C15—C13—C5	111.23 (13)
O6B—C6—C7	111.25 (14)	O7—C14—C9	117.29 (14)
O6A—C6—C5	114.87 (14)	O7—C14—C13	108.38 (13)
O6B—C6—C5	102.05 (13)	C9—C14—C13	108.65 (13)
C7—C6—C5	111.41 (14)	O7—C14—C8	89.75 (13)
C6—O6A—C6A	115.15 (15)	C9—C14—C8	121.07 (14)
O6A—C6A—H6AA	109.5	C13—C14—C8	110.20 (14)
O6A—C6A—H6AB	109.5	O7—C14—C7	46.53 (9)
H6AA—C6A—H6AB	109.5	C9—C14—C7	151.15 (13)
O6A—C6A—H6AC	109.5	C13—C14—C7	99.90 (12)
H6AA—C6A—H6AC	109.5	C8—C14—C7	48.64 (9)
H6AB—C6A—H6AC	109.5	C16—C15—C13	111.98 (14)
C6—O6B—C6B	115.53 (14)	C16—C15—H15A	109.2
O6B—C6B—H6BA	109.5	C13—C15—H15A	109.2
O6B—C6B—H6BB	109.5	C16—C15—H15B	109.2
H6BA—C6B—H6BB	109.5	C13—C15—H15B	109.2
O6B—C6B—H6BC	109.5	H15A—C15—H15B	107.9
H6BA—C6B—H6BC	109.5	N17—C16—C15	109.50 (15)
H6BB—C6B—H6BC	109.5	N17—C16—H16A	109.8
O7—C7—C8	90.10 (13)	C15—C16—H16A	109.8
O7—C7—C6	108.95 (14)	N17—C16—H16B	109.8
C8—C7—C6	111.94 (14)	C15—C16—H16B	109.8
O7—C7—C14	46.41 (8)	H16A—C16—H16B	108.2
C8—C7—C14	49.14 (10)	C17—N17—C16	111.02 (16)
C6—C7—C14	101.61 (12)	C17—N17—C9	112.28 (15)
O7—C7—H7A	114.5	C16—N17—C9	111.34 (14)
C8—C7—H7A	114.5	N17—C17—H17C	109.5
C6—C7—H7A	114.5	N17—C17—H17D	109.5
C14—C7—H7A	143.8	H17C—C17—H17D	109.5
C14—O7—C7	87.06 (12)	N17—C17—H17A	109.5
C7—C8—C14	82.22 (13)	H17C—C17—H17A	109.5
C7—C8—H8A	114.9	H17D—C17—H17A	109.5
C11—C1—C2—C3	−5.5 (3)	C11—C12—C13—C15	82.4 (2)
C1—C2—C3—O3A	−174.20 (18)	C4—C12—C13—C5	4.22 (18)
C1—C2—C3—C4	3.5 (3)	C11—C12—C13—C5	−156.48 (17)
C4—C3—O3A—C3A	−179.55 (17)	O3—C5—C13—C12	−4.67 (17)
C2—C3—O3A—C3A	−1.8 (3)	C6—C5—C13—C12	120.87 (15)
O3A—C3—C4—C12	−175.97 (16)	O3—C5—C13—C14	−114.46 (15)
C2—C3—C4—C12	6.1 (3)	C6—C5—C13—C14	11.09 (19)
O3A—C3—C4—O3	11.6 (3)	O3—C5—C13—C15	119.74 (15)
C2—C3—C4—O3	−166.28 (16)	C6—C5—C13—C15	−114.72 (15)
C12—C4—O3—C5	−0.92 (19)	C7—O7—C14—C9	−150.33 (15)
C3—C4—O3—C5	171.95 (16)	C7—O7—C14—C13	86.26 (14)
C4—O3—C5—C13	3.60 (17)	C7—O7—C14—C8	−24.99 (12)
C4—O3—C5—C6	−121.07 (15)	N17—C9—C14—O7	−61.14 (18)
O3—C5—C6—O6A	−8.5 (2)	C10—C9—C14—O7	172.87 (14)
C13—C5—C6—O6A	−130.38 (15)	N17—C9—C14—C13	62.13 (17)
O3—C5—C6—O6B	−130.85 (14)	C10—C9—C14—C13	−63.86 (18)
C13—C5—C6—O6B	107.30 (15)	N17—C9—C14—C8	−168.91 (15)
O3—C5—C6—C7	110.34 (16)	C10—C9—C14—C8	65.1 (2)
C13—C5—C6—C7	−11.50 (18)	N17—C9—C14—C7	−109.2 (3)
O6B—C6—O6A—C6A	48.0 (2)	C10—C9—C14—C7	124.8 (3)
C7—C6—O6A—C6A	169.14 (14)	C12—C13—C14—O7	−162.52 (14)
C5—C6—O6A—C6A	−68.31 (19)	C15—C13—C14—O7	72.94 (16)
O6A—C6—O6B—C6B	68.66 (19)	C5—C13—C14—O7	−53.10 (17)
C7—C6—O6B—C6B	−48.7 (2)	C12—C13—C14—C9	69.01 (17)
C5—C6—O6B—C6B	−167.58 (15)	C15—C13—C14—C9	−55.52 (17)
O6A—C6—C7—O7	179.38 (13)	C5—C13—C14—C9	178.43 (13)
O6B—C6—C7—O7	−58.53 (18)	C12—C13—C14—C8	−65.78 (16)
C5—C6—C7—O7	54.62 (17)	C15—C13—C14—C8	169.68 (13)
O6A—C6—C7—C8	81.32 (17)	C5—C13—C14—C8	43.64 (18)
O6B—C6—C7—C8	−156.59 (14)	C12—C13—C14—C7	−115.21 (13)
C5—C6—C7—C8	−43.44 (19)	C15—C13—C14—C7	120.26 (13)
O6A—C6—C7—C14	131.73 (12)	C5—C13—C14—C7	−5.79 (16)
O6B—C6—C7—C14	−106.18 (14)	C7—C8—C14—O7	24.11 (12)
C5—C6—C7—C14	6.97 (16)	C7—C8—C14—C9	146.30 (16)
C8—C7—O7—C14	25.20 (12)	C7—C8—C14—C13	−85.43 (15)
C6—C7—O7—C14	−88.11 (14)	C8—C7—C14—O7	−145.74 (17)
O7—C7—C8—C14	−24.06 (12)	C6—C7—C14—O7	105.19 (14)
C6—C7—C8—C14	86.47 (15)	O7—C7—C14—C9	65.7 (3)
N17—C9—C10—C11	−99.08 (18)	C8—C7—C14—C9	−80.0 (3)
C14—C9—C10—C11	22.8 (2)	C6—C7—C14—C9	170.9 (3)
C2—C1—C11—C12	−2.1 (3)	O7—C7—C14—C13	−105.99 (14)
C2—C1—C11—C10	166.60 (18)	C8—C7—C14—C13	108.26 (15)
C9—C10—C11—C12	8.1 (2)	C6—C7—C14—C13	−0.80 (15)
C9—C10—C11—C1	−160.26 (17)	O7—C7—C14—C8	145.74 (17)
O3—C4—C12—C11	158.83 (16)	C6—C7—C14—C8	−109.07 (16)
C3—C4—C12—C11	−14.4 (3)	C12—C13—C15—C16	−65.1 (2)
O3—C4—C12—C13	−2.3 (2)	C14—C13—C15—C16	51.43 (19)
C3—C4—C12—C13	−175.55 (15)	C5—C13—C15—C16	178.79 (14)
C1—C11—C12—C4	12.0 (3)	C13—C15—C16—N17	−53.0 (2)
C10—C11—C12—C4	−157.32 (17)	C15—C16—N17—C17	−172.87 (15)
C1—C11—C12—C13	170.23 (17)	C15—C16—N17—C9	61.24 (19)
C10—C11—C12—C13	0.9 (3)	C14—C9—N17—C17	168.38 (15)
C4—C12—C13—C14	122.12 (15)	C10—C9—N17—C17	−68.4 (2)
C11—C12—C13—C14	−38.6 (2)	C14—C9—N17—C16	−66.43 (18)
C4—C12—C13—C15	−116.90 (17)	C10—C9—N17—C16	56.8 (2)