The title compound, C20H25NO5, which was formed by reaction of 7α-bromohydrocodone-6,6-dimethoxy ketal with KOtBu in tetrahydrofuran, is the first example of a 7,14-bridged oxetane. The geometry of the oxetane ring is consistent with previously reported structures.
Supporting information
CCDC reference: 236061
Key indicators
- Single-crystal X-ray study
- T = 103 K
- Mean (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
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.
Crystal data top
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) Å3 | 0.40 × 0.30 × 0.25 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.0944P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |
Relationship between the four rings of morphonans as determined by
the angle (°) between the least-squares planes for the four rings. topRings | Min | Max | Average | SD | This study |
AB | 5.61 | 25.3 | 19.5 | 4.1 | 25.1 |
ACa | 35.0 | 88.3 | 68.7 | 20.9 | 80.2 |
AD | 74.1 | 89.7 | 79.9 | 3.8 | 72.5 |
BCb | 24.7 | 83.3 | 60.7 | 23.7 | 55.9 |
BD | 79.4 | 87.3 | 84.1 | 1.6 | 87.2 |
CDc | 2.0 | 65.0 | 28.5 | 24.3 | 36.2 |
Notes: (a) bimodal with peaks at approximately 41° and 83°;
(b) bimodal with peaks at approximately 28° and 78°;
(c) bimodal with peaks at approximately 11° and 64°. |