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Strychnine has an interesting oligocyclic structure of seven condensed rings. It is easy to crystallize and gives crystals of excellent quality which diffract nicely to high regions in reciprocal space. It was thus chosen for a comparative charge-density study based on four high-resolution data sets (sin θ/λ ≥ 1.15 Å−1) that were measured with different experimental setups in the temperature range 100–15 K. In addition, a theoretical charge density was derived from a B3LYP/6-311++G(3df,3pd) calculation. The agreement expressed in bond topological parameters among the four experimental charge densities is better than between experiment and theory.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104032781/lc5019sup1.cif
Contains datablocks I, II, III, IV

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Portable Document Format (PDF) file https://doi.org/10.1107/S0108768104032781/lc5019sup2.pdf
Topological parameters of bond critical points

CCDC references: 263181; 263182; 263183; 263184

Computing details top

For all compounds, program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
(I) Strychnine top
Crystal data top
C21H22N2O2F(000) = 712
Mr = 334.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9605 reflections
Hall symbol: P 2ac 2abθ = 2.4–48.1°
a = 11.309 (1) ŵ = 0.09 mm1
b = 11.785 (1) ÅT = 100 K
c = 12.002 (1) Å, colorless
V = 1599.65 Å3 × × mm
Z = 4
Data collection top
Graphit monochromatork = ??
h = ??l = ??
Refinement top
Refinement on F922 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.017 w1 = 1/[s2(Fo)]
wR(F2) = 0.018(Δ/σ)max = 0.199
S = 0.47Δρmax = 0.16 e Å3
8480 reflectionsΔρmin = 0.12 e Å3
Crystal data top
C21H22N2O2V = 1599.65 Å3
Mr = 334.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.309 (1) ŵ = 0.09 mm1
b = 11.785 (1) ÅT = 100 K
c = 12.002 (1) Å × × mm
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.0170 restraints
wR(F2) = 0.018(Δ/σ)max = 0.199
S = 0.47Δρmax = 0.16 e Å3
8480 reflectionsΔρmin = 0.12 e Å3
922 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(18)0.46181 (4)0.01375 (4)1.00018 (4)0.017
O(21)0.86966 (5)0.00814 (6)0.91712 (5)0.023
N(5)0.72464 (3)0.08375 (3)0.82042 (3)0.014
N(14)0.39488 (4)0.29316 (4)0.73309 (4)0.016
C(1)0.51646 (4)0.32437 (3)0.77083 (3)0.014
C(2)0.51918 (4)0.35233 (3)0.89468 (3)0.016
C(3)0.47915 (4)0.24742 (3)0.96031 (3)0.014
C(4)0.57745 (3)0.15835 (3)0.94680 (3)0.012
C(5)0.60075 (3)0.12584 (3)0.82486 (3)0.012
C(6)0.79607 (3)0.16277 (4)0.76242 (3)0.015
C(7)0.91829 (4)0.16224 (6)0.74561 (4)0.02
C(8)0.96747 (5)0.25315 (7)0.68605 (4)0.024
C(9)0.89741 (5)0.34119 (6)0.64427 (4)0.023
C(10)0.77492 (5)0.33842 (5)0.65957 (4)0.019
C(11)0.72473 (3)0.24903 (4)0.71844 (3)0.014
C(12)0.59605 (3)0.22322 (3)0.73738 (3)0.012
C(13)0.53304 (4)0.18483 (4)0.62963 (3)0.014
C(14)0.40301 (4)0.19058 (4)0.66296 (4)0.016
C(15)0.30927 (4)0.28227 (5)0.82451 (4)0.019
C(16)0.35825 (4)0.21038 (4)0.91766 (4)0.016
C(17)0.30330 (4)0.11761 (5)0.95628 (4)0.018
C(18)0.35877 (5)0.04200 (5)1.04292 (4)0.019
C(19)0.56943 (4)0.04826 (3)1.01485 (3)0.014
C(20)0.66813 (4)0.03441 (4)0.97819 (4)0.016
C(21)0.76424 (4)0.01432 (4)0.90431 (3)0.016
H(1)0.548620.396130.725530.022 (4)
H(2A)0.46170.422730.911320.051 (5)
H(2B)0.608660.375570.914060.027 (4)
H(3)0.468010.269011.046190.032 (4)
H(4)0.65610.202060.97170.028 (3)
H(5)0.543350.05840.79920.023 (3)
H(7)0.972330.091790.773660.036 (4)
H(8)1.062470.251280.674880.040 (5)
H(9)0.939320.410490.600560.056 (6)
H(10)0.719320.404970.626210.037 (5)
H(13A)0.553960.242450.563220.022 (4)
H(13B)0.564030.103820.601160.018 (4)
H(14A)0.343770.19580.593420.028 (4)
H(14B)0.379190.119040.713670.021 (4)
H(15A)0.232740.243080.788220.026 (4)
H(15B)0.285330.36570.852510.050 (5)
H(17)0.219110.096840.921580.044 (5)
H(18A)0.380270.086431.118270.029 (5)
H(18B)0.29880.022921.069940.025 (4)
H(19)0.575350.067531.101740.022 (3)
H(20A)0.709060.072511.049490.025 (5)
H(20B)0.624080.099130.931060.033 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(18)0.01880 (10)0.01530 (10)0.01570 (10)0.00260 (10)0.00100 (10)0.00080 (10)
O(21)0.0174 (2)0.0305 (2)0.0223 (2)0.0103 (2)0.00190 (10)0.0045 (2)
N(5)0.01320 (10)0.01510 (10)0.01260 (10)0.00310 (10)0.00040 (10)0.00040 (10)
N(14)0.01490 (10)0.01730 (10)0.01540 (10)0.00330 (10)0.00120 (10)0.00040 (10)
C(1)0.01640 (10)0.01170 (10)0.01390 (10)0.00170 (10)0.00030 (10)0.00040 (10)
C(2)0.02020 (10)0.01190 (10)0.01520 (10)0.00140 (10)0.00020 (10)0.00180 (10)
C(3)0.01600 (10)0.01380 (10)0.01250 (10)0.00160 (10)0.00120 (10)0.00200 (10)
C(4)0.01400 (10)0.01200 (10)0.01090 (10)0.00030 (10)0.00030 (10)0.00080 (10)
C(5)0.01250 (10)0.01130 (10)0.01070 (10)0.00070 (10)0.00040 (10)0.00010 (10)
C(6)0.01190 (10)0.01980 (10)0.01210 (10)0.00100 (10)0.00040 (10)0.00090 (10)
C(7)0.01240 (10)0.0331 (2)0.01490 (10)0.00150 (10)0.00090 (10)0.00190 (10)
C(8)0.01420 (10)0.0409 (3)0.0162 (2)0.0059 (2)0.00230 (10)0.0016 (2)
C(9)0.0192 (2)0.0333 (2)0.0167 (2)0.0099 (2)0.00250 (10)0.0010 (2)
C(10)0.0193 (2)0.0207 (2)0.01590 (10)0.00580 (10)0.00190 (10)0.00240 (10)
C(11)0.01330 (10)0.01600 (10)0.01240 (10)0.00140 (10)0.00070 (10)0.00050 (10)
C(12)0.01260 (10)0.01210 (10)0.01110 (10)0.00030 (10)0.00030 (10)0.00030 (10)
C(13)0.01590 (10)0.01550 (10)0.01150 (10)0.00040 (10)0.00130 (10)0.00030 (10)
C(14)0.01470 (10)0.01850 (10)0.01550 (10)0.00010 (10)0.00270 (10)0.00030 (10)
C(15)0.01460 (10)0.0235 (2)0.0195 (2)0.00580 (10)0.00100 (10)0.00080 (10)
C(16)0.01380 (10)0.01840 (10)0.01580 (10)0.00200 (10)0.00210 (10)0.00060 (10)
C(17)0.01470 (10)0.0214 (2)0.0184 (2)0.00100 (10)0.00330 (10)0.00070 (10)
C(18)0.0199 (2)0.0219 (2)0.01630 (10)0.00320 (10)0.00470 (10)0.00090 (10)
C(19)0.01740 (10)0.01370 (10)0.01120 (10)0.00020 (10)0.00070 (10)0.00040 (10)
C(20)0.01990 (10)0.01410 (10)0.01550 (10)0.00260 (10)0.00210 (10)0.00170 (10)
C(21)0.01600 (10)0.01740 (10)0.01390 (10)0.00560 (10)0.00180 (10)0.00050 (10)
Geometric parameters (Å, º) top
O(18)—C(18)1.4328 (7)C(9)—H(9)1.0803 (6)
O(18)—C(19)1.4305 (6)C(10)—C(11)1.3897 (6)
O(21)—C(21)1.2309 (6)C(10)—H(10)1.0820 (6)
N(5)—C(5)1.4873 (5)C(11)—C(12)1.5039 (5)
N(5)—C(6)1.4158 (6)C(12)—C(13)1.5444 (5)
N(5)—C(21)1.3725 (5)C(13)—C(14)1.5255 (6)
N(14)—C(1)1.4935 (6)C(13)—H(13A)1.0735 (4)
N(14)—C(14)1.4760 (6)C(13)—H(13B)1.0729 (4)
N(14)—C(15)1.4688 (6)C(14)—H(14A)1.0720 (4)
C(1)—C(2)1.5229 (5)C(14)—H(14B)1.0741 (5)
C(1)—C(12)1.5467 (5)C(15)—C(16)1.5083 (7)
C(1)—H(1)1.0693 (4)C(15)—H(15A)1.0733 (5)
C(2)—C(3)1.5343 (6)C(15)—H(15B)1.0738 (5)
C(2)—H(2A)1.0728 (4)C(16)—C(17)1.3403 (7)
C(2)—H(2B)1.0738 (5)C(17)—C(18)1.5062 (7)
C(3)—C(4)1.5376 (5)C(17)—H(17)1.0677 (5)
C(3)—C(16)1.5237 (6)C(18)—H(18A)1.0729 (5)
C(3)—H(3)1.0691 (4)C(18)—H(18B)1.0726 (5)
C(4)—C(5)1.5356 (5)C(19)—C(20)1.5455 (6)
C(4)—C(19)1.5358 (5)C(19)—H(19)1.0693 (4)
C(4)—H(4)1.0704 (4)C(20)—C(21)1.5157 (7)
C(5)—C(12)1.5564 (5)C(20)—H(20A)1.0715 (4)
C(5)—H(5)1.0714 (4)C(20)—H(20B)1.0724 (5)
C(6)—C(7)1.3968 (6)H(2A)—H(2B)1.7527
C(6)—C(11)1.4012 (6)H(13A)—H(13B)1.7000
C(7)—C(8)1.4030 (9)H(14A)—H(14B)1.7498
C(7)—H(7)1.0846 (6)H(15A)—H(15B)1.7429
C(8)—C(9)1.3986 (10)H(18A)—H(18B)1.6871
C(8)—H(8)1.0828 (5)H(20A)—H(20B)1.7443
C(9)—C(10)1.3977 (8)
C(18)—O(18)—C(19)114.43 (4)C(5)—C(12)—C(13)111.38 (3)
C(5)—N(5)—C(6)109.61 (3)C(11)—C(12)—C(13)112.28 (3)
C(5)—N(5)—C(21)118.68 (4)C(12)—C(13)—C(14)102.25 (3)
C(6)—N(5)—C(21)124.52 (4)C(12)—C(13)—H(13A)109.55 (3)
C(1)—N(14)—C(14)108.50 (3)C(12)—C(13)—H(13B)112.13 (3)
C(1)—N(14)—C(15)113.69 (4)C(14)—C(13)—H(13A)112.27 (4)
C(14)—N(14)—C(15)113.29 (4)C(14)—C(13)—H(13B)115.97 (4)
N(14)—C(1)—C(2)111.59 (4)H(13A)—C(13)—H(13B)104.75 (3)
N(14)—C(1)—C(12)105.50 (3)N(14)—C(14)—C(13)104.24 (4)
N(14)—C(1)—H(1)110.71 (3)N(14)—C(14)—H(14A)110.99 (4)
C(2)—C(1)—C(12)114.10 (3)N(14)—C(14)—H(14B)107.71 (4)
C(2)—C(1)—H(1)108.56 (3)C(13)—C(14)—H(14A)113.62 (4)
C(12)—C(1)—H(1)106.25 (3)C(13)—C(14)—H(14B)110.82 (4)
C(1)—C(2)—C(3)108.70 (3)H(14A)—C(14)—H(14B)109.24 (4)
C(1)—C(2)—H(2A)109.68 (4)N(14)—C(15)—C(16)111.15 (4)
C(1)—C(2)—H(2B)106.60 (4)N(14)—C(15)—H(15A)105.43 (4)
C(3)—C(2)—H(2A)110.42 (4)N(14)—C(15)—H(15B)108.66 (5)
C(3)—C(2)—H(2B)111.86 (4)C(16)—C(15)—H(15A)110.80 (5)
H(2A)—C(2)—H(2B)109.48 (3)C(16)—C(15)—H(15B)112.02 (4)
C(2)—C(3)—C(4)106.42 (3)H(15A)—C(15)—H(15B)108.53 (4)
C(2)—C(3)—C(16)108.86 (3)C(3)—C(16)—C(15)114.68 (4)
C(2)—C(3)—H(3)109.75 (3)C(3)—C(16)—C(17)122.25 (4)
C(4)—C(3)—C(16)114.69 (3)C(15)—C(16)—C(17)122.98 (5)
C(4)—C(3)—H(3)110.44 (3)C(16)—C(17)—C(18)121.89 (4)
C(16)—C(3)—H(3)106.64 (3)C(16)—C(17)—H(17)117.75 (5)
C(3)—C(4)—C(5)113.26 (3)C(18)—C(17)—H(17)120.33 (5)
C(3)—C(4)—C(19)118.56 (3)O(18)—C(18)—C(17)111.27 (4)
C(3)—C(4)—H(4)104.05 (3)O(18)—C(18)—H(18A)109.95 (5)
C(5)—C(4)—C(19)107.83 (3)O(18)—C(18)—H(18B)107.18 (5)
C(5)—C(4)—H(4)104.10 (3)C(17)—C(18)—H(18A)112.80 (5)
C(19)—C(4)—H(4)107.89 (3)C(17)—C(18)—H(18B)111.56 (5)
N(5)—C(5)—C(4)106.20 (3)H(18A)—C(18)—H(18B)103.68 (4)
N(5)—C(5)—C(12)104.71 (3)O(18)—C(19)—C(4)114.60 (4)
N(5)—C(5)—H(5)108.24 (3)O(18)—C(19)—C(20)104.91 (4)
C(4)—C(5)—C(12)116.94 (3)O(18)—C(19)—H(19)106.37 (4)
C(4)—C(5)—H(5)110.80 (3)C(4)—C(19)—C(20)109.79 (3)
C(12)—C(5)—H(5)109.42 (3)C(4)—C(19)—H(19)109.60 (3)
N(5)—C(6)—C(7)129.25 (5)C(20)—C(19)—H(19)111.49 (3)
N(5)—C(6)—C(11)109.51 (3)C(19)—C(20)—C(21)116.46 (3)
C(7)—C(6)—C(11)121.24 (4)C(19)—C(20)—H(20A)110.41 (4)
C(6)—C(7)—C(8)117.54 (5)C(19)—C(20)—H(20B)105.25 (4)
C(6)—C(7)—H(7)121.07 (5)C(21)—C(20)—H(20A)108.43 (4)
C(8)—C(7)—H(7)121.30 (5)C(21)—C(20)—H(20B)107.10 (4)
C(7)—C(8)—C(9)121.65 (5)H(20A)—C(20)—H(20B)108.90 (4)
C(7)—C(8)—H(8)116.16 (7)O(21)—C(21)—N(5)122.40 (5)
C(9)—C(8)—H(8)122.19 (6)O(21)—C(21)—C(20)122.68 (5)
C(8)—C(9)—C(10)119.81 (5)N(5)—C(21)—C(20)114.91 (4)
C(8)—C(9)—H(9)119.11 (5)C(2)—H(2A)—H(2B)35.28 (2)
C(10)—C(9)—H(9)121.08 (7)C(2)—H(2B)—H(2A)35.24 (2)
C(9)—C(10)—C(11)119.29 (5)C(13)—H(13A)—H(13B)37.61 (2)
C(9)—C(10)—H(10)120.69 (5)C(13)—H(13B)—H(13A)37.64 (2)
C(11)—C(10)—H(10)120.02 (4)C(14)—H(14A)—H(14B)35.42 (3)
C(6)—C(11)—C(10)120.42 (4)C(14)—H(14B)—H(14A)35.34 (2)
C(6)—C(11)—C(12)110.70 (3)C(15)—H(15A)—H(15B)35.75 (3)
C(10)—C(11)—C(12)128.71 (4)C(15)—H(15B)—H(15A)35.73 (3)
C(1)—C(12)—C(5)114.40 (3)C(18)—H(18A)—H(18B)38.15 (3)
C(1)—C(12)—C(11)116.51 (3)C(18)—H(18B)—H(18A)38.16 (3)
C(1)—C(12)—C(13)100.06 (3)C(20)—H(20A)—H(20B)35.57 (2)
C(5)—C(12)—C(11)102.60 (3)C(20)—H(20B)—H(20A)35.53 (2)
(II) Strychnine top
Crystal data top
C21H22N2O2F(000) = 712
Mr = 334.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8611 reflections
Hall symbol: P 2ac 2abθ = 2.4–37.7°
a = 11.326 (1) ŵ = 0.09 mm1
b = 11.765 (1) ÅT = 25 K
c = 11.994 (1) Å, colorless
V = 1598.23 Å3 × × mm
Z = 4
Data collection top
Radiation source: sealed X-ray tubek = ??
Graphit monochromatorl = ??
h = ??
Refinement top
Refinement on F922 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.017 w1 = 1/[s2(Fo)]
wR(F2) = 0.018(Δ/σ)max = 0.003
S = 0.93Δρmax = 0.19 e Å3
9430 reflectionsΔρmin = 0.11 e Å3
Crystal data top
C21H22N2O2V = 1598.23 Å3
Mr = 334.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.326 (1) ŵ = 0.09 mm1
b = 11.765 (1) ÅT = 25 K
c = 11.994 (1) Å × × mm
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.017922 parameters
wR(F2) = 0.0180 restraints
S = 0.93Δρmax = 0.19 e Å3
9430 reflectionsΔρmin = 0.11 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(18)0.46221 (4)0.01401 (3)1.00074 (3)0.01
O(21)0.86980 (4)0.00856 (5)0.91700 (4)0.014
N(5)0.72494 (3)0.08403 (3)0.82039 (3)0.008
N(14)0.39487 (3)0.29342 (3)0.73318 (3)0.01
C(1)0.51641 (3)0.32478 (3)0.77090 (3)0.009
C(2)0.51928 (4)0.35290 (3)0.89489 (3)0.01
C(3)0.47940 (3)0.24768 (3)0.96068 (3)0.009
C(4)0.57772 (3)0.15851 (3)0.94712 (3)0.008
C(5)0.60096 (3)0.12591 (3)0.82495 (3)0.007
C(6)0.79614 (3)0.16320 (3)0.76226 (3)0.009
C(7)0.91839 (4)0.16266 (4)0.74528 (3)0.012
C(8)0.96748 (4)0.25370 (5)0.68553 (4)0.014
C(9)0.89736 (4)0.34188 (5)0.64379 (4)0.014
C(10)0.77473 (4)0.33900 (4)0.65910 (3)0.011
C(11)0.72478 (3)0.24952 (3)0.71820 (3)0.009
C(12)0.59602 (3)0.22350 (3)0.73728 (3)0.007
C(13)0.53303 (3)0.18504 (3)0.62941 (3)0.009
C(14)0.40296 (4)0.19055 (3)0.66307 (3)0.01
C(15)0.30934 (4)0.28253 (4)0.82490 (4)0.012
C(16)0.35860 (3)0.21060 (3)0.91819 (3)0.01
C(17)0.30358 (4)0.11761 (4)0.95701 (3)0.011
C(18)0.35932 (4)0.04184 (4)1.04373 (4)0.012
C(19)0.56986 (3)0.04807 (3)1.01524 (3)0.009
C(20)0.66853 (4)0.03466 (3)0.97824 (3)0.01
C(21)0.76467 (3)0.01436 (3)0.90441 (3)0.009
H(1)0.547510.397330.725780.011 (3)
H(2A)0.460110.421550.91330.029 (4)
H(2B)0.607810.378220.914970.027 (4)
H(3)0.473070.269231.04710.022 (3)
H(4)0.656310.201450.973130.026 (3)
H(5)0.544180.057830.799530.021 (3)
H(7)0.976710.096090.775050.016 (3)
H(8)1.062240.253380.673590.029 (4)
H(9)0.938310.41190.599790.032 (5)
H(10)0.719050.406140.626460.033 (5)
H(13A)0.552940.244110.563780.022 (4)
H(13B)0.564270.104220.600510.017 (4)
H(14A)0.342930.193280.593870.025 (4)
H(14B)0.378530.118370.712760.014 (3)
H(15A)0.231770.244940.789060.031 (4)
H(15B)0.28930.366290.854790.027 (4)
H(17)0.219040.095240.924050.033 (4)
H(18A)0.381150.086331.119120.023 (4)
H(18B)0.29880.023891.067730.016 (4)
H(19)0.574980.0671.102310.014 (3)
H(20A)0.707940.075551.048970.014 (4)
H(20B)0.623690.099420.931640.016 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(18)0.01030 (10)0.00940 (10)0.01070 (10)0.00150 (10)0.00060 (10)0.00030 (10)
O(21)0.00970 (10)0.0190 (2)0.01390 (10)0.00600 (10)0.00080 (10)0.00280 (10)
N(5)0.00804 (9)0.00943 (11)0.00796 (9)0.00201 (9)0.00002 (8)0.00068 (9)
N(14)0.00930 (10)0.01060 (10)0.00910 (10)0.00190 (10)0.00040 (10)0.00020 (10)
C(1)0.01010 (10)0.00720 (10)0.00840 (10)0.00100 (10)0.00010 (10)0.00030 (10)
C(2)0.01290 (10)0.00720 (10)0.00930 (10)0.00080 (10)0.00010 (10)0.00100 (10)
C(3)0.00990 (10)0.00830 (10)0.00790 (10)0.00090 (10)0.00060 (10)0.00090 (10)
C(4)0.00830 (10)0.00740 (10)0.00690 (10)0.00030 (10)0.00020 (10)0.00030 (10)
C(5)0.00794 (9)0.00689 (10)0.00666 (9)0.00051 (8)0.00017 (8)0.00007 (8)
C(6)0.00760 (10)0.01180 (10)0.00770 (10)0.00060 (10)0.00040 (10)0.00010 (10)
C(7)0.00800 (10)0.0192 (2)0.00980 (10)0.00110 (10)0.00060 (10)0.00060 (10)
C(8)0.00880 (10)0.0240 (2)0.01050 (10)0.00320 (10)0.00140 (10)0.00030 (10)
C(9)0.01170 (10)0.0195 (2)0.01090 (10)0.00560 (10)0.00160 (10)0.00100 (10)
C(10)0.01140 (10)0.01280 (10)0.01020 (10)0.00320 (10)0.00090 (10)0.00180 (10)
C(11)0.00830 (10)0.00960 (10)0.00780 (10)0.00100 (10)0.00060 (10)0.00080 (10)
C(12)0.00800 (10)0.00730 (10)0.00680 (10)0.00030 (10)0.00000 (10)0.00020 (10)
C(13)0.00960 (10)0.01000 (10)0.00730 (10)0.00020 (10)0.00070 (10)0.00040 (10)
C(14)0.00930 (10)0.01130 (10)0.00980 (10)0.00000 (10)0.00150 (10)0.00050 (10)
C(15)0.00900 (10)0.01400 (10)0.01160 (10)0.00350 (10)0.00070 (10)0.00080 (10)
C(16)0.00880 (10)0.01090 (10)0.00950 (10)0.00100 (10)0.00110 (10)0.00000 (10)
C(17)0.00940 (10)0.01270 (10)0.01140 (10)0.00070 (10)0.00150 (10)0.00000 (10)
C(18)0.01170 (10)0.01350 (10)0.01020 (10)0.00160 (10)0.00260 (10)0.00090 (10)
C(19)0.01030 (10)0.00840 (10)0.00700 (10)0.00010 (10)0.00030 (10)0.00030 (10)
C(20)0.01180 (10)0.00900 (10)0.00980 (10)0.00180 (10)0.00080 (10)0.00140 (10)
C(21)0.00960 (10)0.01050 (10)0.00840 (10)0.00320 (10)0.00090 (10)0.00050 (10)
Geometric parameters (Å, º) top
O(18)—C(18)1.4338 (6)C(9)—H(9)1.0827 (5)
O(18)—C(19)1.4319 (5)C(10)—C(11)1.3896 (5)
O(21)—C(21)1.2301 (6)C(10)—H(10)1.0840 (5)
N(5)—C(5)1.4891 (5)C(11)—C(12)1.5076 (5)
N(5)—C(6)1.4156 (5)C(12)—C(13)1.5452 (5)
N(5)—C(21)1.3747 (5)C(13)—C(14)1.5288 (5)
N(14)—C(1)1.4952 (5)C(13)—H(13A)1.0740 (4)
N(14)—C(14)1.4766 (5)C(13)—H(13B)1.0722 (4)
N(14)—C(15)1.4715 (5)C(14)—H(14A)1.0733 (4)
C(1)—C(2)1.5238 (5)C(14)—H(14B)1.0737 (4)
C(1)—C(12)1.5477 (5)C(15)—C(16)1.5098 (6)
C(1)—H(1)1.0703 (4)C(15)—H(15A)1.0735 (4)
C(2)—C(3)1.5359 (5)C(15)—H(15B)1.0729 (4)
C(2)—H(2A)1.0725 (4)C(16)—C(17)1.3425 (6)
C(2)—H(2B)1.0734 (4)C(17)—C(18)1.5083 (6)
C(3)—C(4)1.5385 (5)C(17)—H(17)1.0689 (4)
C(3)—C(16)1.5238 (5)C(18)—H(18A)1.0736 (4)
C(3)—H(3)1.0696 (3)C(18)—H(18B)1.0727 (4)
C(4)—C(5)1.5374 (5)C(19)—C(20)1.5470 (5)
C(4)—C(19)1.5374 (5)C(19)—H(19)1.0694 (4)
C(4)—H(4)1.0699 (4)C(20)—C(21)1.5175 (6)
C(5)—C(12)1.5579 (5)C(20)—H(20A)1.0726 (4)
C(5)—H(5)1.0715 (4)C(20)—H(20B)1.0727 (4)
C(6)—C(7)1.3996 (5)H(2A)—H(2B)1.7488
C(6)—C(11)1.4014 (5)H(13A)—H(13B)1.7085
C(7)—C(8)1.4036 (7)H(14A)—H(14B)1.7240
C(7)—H(7)1.0849 (5)H(15A)—H(15B)1.7563
C(8)—C(9)1.3991 (7)H(18A)—H(18B)1.7121
C(8)—H(8)1.0828 (4)H(20A)—H(20B)1.7234
C(9)—C(10)1.4014 (6)
C(18)—O(18)—C(19)114.50 (4)C(5)—C(12)—C(13)111.47 (3)
C(5)—N(5)—C(6)109.73 (3)C(11)—C(12)—C(13)112.27 (3)
C(5)—N(5)—C(21)118.62 (3)C(12)—C(13)—C(14)102.20 (3)
C(6)—N(5)—C(21)124.53 (3)C(12)—C(13)—H(13A)109.11 (3)
C(1)—N(14)—C(14)108.51 (3)C(12)—C(13)—H(13B)112.21 (3)
C(1)—N(14)—C(15)113.66 (3)C(14)—C(13)—H(13A)111.62 (3)
C(14)—N(14)—C(15)113.28 (4)C(14)—C(13)—H(13B)116.17 (3)
N(14)—C(1)—C(2)111.62 (3)H(13A)—C(13)—H(13B)105.52 (3)
N(14)—C(1)—C(12)105.52 (3)N(14)—C(14)—C(13)104.17 (3)
N(14)—C(1)—H(1)110.29 (3)N(14)—C(14)—H(14A)112.12 (3)
C(2)—C(1)—C(12)114.14 (3)N(14)—C(14)—H(14B)108.43 (3)
C(2)—C(1)—H(1)108.26 (3)C(13)—C(14)—H(14A)114.04 (3)
C(12)—C(1)—H(1)106.89 (3)C(13)—C(14)—H(14B)111.19 (3)
C(1)—C(2)—C(3)108.67 (3)H(14A)—C(14)—H(14B)106.83 (3)
C(1)—C(2)—H(2A)110.56 (3)N(14)—C(15)—C(16)111.07 (3)
C(1)—C(2)—H(2B)107.40 (3)N(14)—C(15)—H(15A)105.98 (4)
C(3)—C(2)—H(2A)108.51 (3)N(14)—C(15)—H(15B)108.00 (4)
C(3)—C(2)—H(2B)112.53 (3)C(16)—C(15)—H(15A)111.61 (4)
H(2A)—C(2)—H(2B)109.17 (3)C(16)—C(15)—H(15B)110.21 (4)
C(2)—C(3)—C(4)106.41 (3)H(15A)—C(15)—H(15B)109.82 (3)
C(2)—C(3)—C(16)108.84 (3)C(3)—C(16)—C(15)114.79 (3)
C(2)—C(3)—H(3)109.06 (3)C(3)—C(16)—C(17)122.28 (4)
C(4)—C(3)—C(16)114.80 (3)C(15)—C(16)—C(17)122.84 (4)
C(4)—C(3)—H(3)108.22 (3)C(16)—C(17)—C(18)121.77 (4)
C(16)—C(3)—H(3)109.38 (3)C(16)—C(17)—H(17)119.22 (4)
C(3)—C(4)—C(5)113.25 (3)C(18)—C(17)—H(17)118.98 (4)
C(3)—C(4)—C(19)118.57 (3)O(18)—C(18)—C(17)111.29 (3)
C(3)—C(4)—H(4)104.44 (3)O(18)—C(18)—H(18A)109.83 (4)
C(5)—C(4)—C(19)107.79 (3)O(18)—C(18)—H(18B)106.59 (4)
C(5)—C(4)—H(4)104.67 (3)C(17)—C(18)—H(18A)112.90 (4)
C(19)—C(4)—H(4)107.00 (3)C(17)—C(18)—H(18B)110.10 (4)
N(5)—C(5)—C(4)106.20 (3)H(18A)—C(18)—H(18B)105.82 (3)
N(5)—C(5)—C(12)104.65 (3)O(18)—C(19)—C(4)114.57 (3)
N(5)—C(5)—H(5)107.95 (3)O(18)—C(19)—C(20)105.03 (3)
C(4)—C(5)—C(12)116.95 (3)O(18)—C(19)—H(19)105.72 (3)
C(4)—C(5)—H(5)110.79 (3)C(4)—C(19)—C(20)109.72 (3)
C(12)—C(5)—H(5)109.71 (3)C(4)—C(19)—H(19)109.87 (3)
N(5)—C(6)—C(7)129.21 (4)C(20)—C(19)—H(19)111.84 (3)
N(5)—C(6)—C(11)109.52 (3)C(19)—C(20)—C(21)116.53 (3)
C(7)—C(6)—C(11)121.27 (4)C(19)—C(20)—H(20A)110.85 (3)
C(6)—C(7)—C(8)117.56 (4)C(19)—C(20)—H(20B)104.74 (3)
C(6)—C(7)—H(7)123.89 (4)C(21)—C(20)—H(20A)109.48 (3)
C(8)—C(7)—H(7)118.54 (4)C(21)—C(20)—H(20B)107.79 (3)
C(7)—C(8)—C(9)121.58 (4)H(20A)—C(20)—H(20B)106.90 (3)
C(7)—C(8)—H(8)117.22 (5)O(21)—C(21)—N(5)122.52 (4)
C(9)—C(8)—H(8)121.19 (5)O(21)—C(21)—C(20)122.66 (4)
C(8)—C(9)—C(10)119.85 (4)N(5)—C(21)—C(20)114.80 (3)
C(8)—C(9)—H(9)119.70 (4)C(2)—H(2A)—H(2B)35.43 (2)
C(10)—C(9)—H(9)120.45 (5)C(2)—H(2B)—H(2A)35.40 (2)
C(9)—C(10)—C(11)119.25 (4)C(13)—H(13A)—H(13B)37.21 (2)
C(9)—C(10)—H(10)120.78 (4)C(13)—H(13B)—H(13A)37.28 (2)
C(11)—C(10)—H(10)119.96 (4)C(14)—H(14A)—H(14B)36.59 (2)
C(6)—C(11)—C(10)120.44 (4)C(14)—H(14B)—H(14A)36.58 (2)
C(6)—C(11)—C(12)110.70 (3)C(15)—H(15A)—H(15B)35.08 (2)
C(10)—C(11)—C(12)128.70 (4)C(15)—H(15B)—H(15A)35.10 (2)
C(1)—C(12)—C(5)114.36 (3)C(18)—H(18A)—H(18B)37.07 (2)
C(1)—C(12)—C(11)116.54 (3)C(18)—H(18B)—H(18A)37.11 (2)
C(1)—C(12)—C(13)100.05 (3)C(20)—H(20A)—H(20B)36.55 (2)
C(5)—C(12)—C(11)102.56 (3)C(20)—H(20B)—H(20A)36.55 (2)
(III) Strychnine top
Crystal data top
C21H22N2O2F(000) = 712
Mr = 334.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9605 reflections
Hall symbol: P 2ac 2abθ = 2.4–48.1°
a = 11.309 (1) ŵ = 0.09 mm1
b = 11.785 (1) ÅT = 100 K
c = 12.002 (1) Å, colorless
V = 1599.65 Å3 × × mm
Z = 4
Data collection top
Graphit monochromatork = ??
h = ??l = ??
Refinement top
Refinement on F922 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.023 w1 = 1/[s2(Fo)]
wR(F2) = 0.016(Δ/σ)max = 0.007
S = 0.69Δρmax = 0.16 e Å3
8192 reflectionsΔρmin = 0.14 e Å3
Crystal data top
C21H22N2O2V = 1599.65 Å3
Mr = 334.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.309 (1) ŵ = 0.09 mm1
b = 11.785 (1) ÅT = 100 K
c = 12.002 (1) Å × × mm
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.023922 parameters
wR(F2) = 0.0160 restraints
S = 0.69Δρmax = 0.16 e Å3
8192 reflectionsΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(18)0.46182 (6)0.01367 (5)1.00005 (5)0.016
O(21)0.86963 (7)0.00822 (8)0.91699 (7)0.023
N(5)0.72458 (5)0.08373 (4)0.82044 (4)0.013
N(14)0.39492 (5)0.29304 (5)0.73304 (4)0.015
C(1)0.51649 (5)0.32417 (4)0.77089 (4)0.013
C(2)0.51920 (6)0.35216 (4)0.89457 (4)0.015
C(3)0.47906 (5)0.24727 (4)0.96020 (4)0.013
C(4)0.57741 (4)0.15832 (4)0.94670 (3)0.011
C(5)0.60072 (4)0.12578 (4)0.82488 (3)0.01
C(6)0.79604 (5)0.16261 (5)0.76248 (4)0.013
C(7)0.91823 (5)0.16214 (7)0.74561 (5)0.019
C(8)0.96747 (6)0.25304 (9)0.68618 (5)0.023
C(9)0.89753 (7)0.34090 (8)0.64443 (5)0.023
C(10)0.77501 (6)0.33822 (6)0.65972 (4)0.018
C(11)0.72480 (5)0.24884 (5)0.71847 (4)0.013
C(12)0.59608 (4)0.22316 (4)0.73733 (3)0.011
C(13)0.53308 (5)0.18476 (4)0.62968 (4)0.013
C(14)0.40298 (5)0.19053 (5)0.66291 (4)0.015
C(15)0.30938 (5)0.28212 (6)0.82451 (5)0.018
C(16)0.35831 (5)0.21040 (5)0.91753 (4)0.015
C(17)0.30322 (6)0.11769 (6)0.95614 (5)0.017
C(18)0.35871 (6)0.04199 (6)1.04266 (5)0.019
C(19)0.56924 (5)0.04826 (4)1.01477 (4)0.013
C(20)0.66808 (6)0.03433 (5)0.97822 (5)0.015
C(21)0.76424 (5)0.01423 (5)0.90421 (4)0.015
H(1)0.548120.395620.724580.026 (4)
H(2A)0.46160.4220.912740.038 (4)
H(2B)0.608230.375250.915940.031 (4)
H(3)0.470530.269671.046160.033 (4)
H(4)0.657020.20040.971540.026 (4)
H(5)0.54190.059290.79970.024 (4)
H(7)0.972250.092490.775780.030 (4)
H(8)1.062170.252190.673480.044 (6)
H(9)0.937470.411240.60070.044 (6)
H(10)0.719710.404520.625230.037 (5)
H(13A)0.554270.242420.563380.030 (4)
H(13B)0.563850.103960.600590.026 (4)
H(14A)0.344020.192980.592980.034 (5)
H(14B)0.376320.119610.713090.030 (4)
H(15A)0.231860.243450.789360.037 (5)
H(15B)0.289150.365580.854790.035 (5)
H(17)0.218370.096560.923170.044 (6)
H(18A)0.379450.086051.11850.036 (5)
H(18B)0.298510.023281.068350.027 (4)
H(19)0.575710.069271.101210.024 (4)
H(20A)0.707150.074891.049240.025 (4)
H(20B)0.623760.101540.934830.026 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(18)0.0177 (2)0.0137 (2)0.0152 (2)0.0026 (2)0.0011 (2)0.00070 (10)
O(21)0.0169 (2)0.0301 (3)0.0221 (2)0.0104 (2)0.0022 (2)0.0047 (2)
N(5)0.0118 (2)0.0143 (2)0.01160 (10)0.00300 (10)0.00010 (10)0.00050 (10)
N(14)0.0141 (2)0.0160 (2)0.01470 (10)0.00360 (10)0.00110 (10)0.00050 (10)
C(1)0.0155 (2)0.01000 (10)0.01300 (10)0.00190 (10)0.00030 (10)0.00050 (10)
C(2)0.0199 (2)0.01020 (10)0.01420 (10)0.0016 (2)0.00030 (10)0.00180 (10)
C(3)0.0153 (2)0.01240 (10)0.01130 (10)0.00170 (10)0.00120 (10)0.00200 (10)
C(4)0.0130 (2)0.01010 (10)0.00950 (10)0.00040 (10)0.00020 (10)0.00070 (10)
C(5)0.01110 (10)0.00960 (10)0.00940 (10)0.00070 (10)0.00030 (10)0.00010 (10)
C(6)0.0107 (2)0.0192 (2)0.01050 (10)0.00110 (10)0.00030 (10)0.00110 (10)
C(7)0.0112 (2)0.0328 (3)0.0137 (2)0.0013 (2)0.00100 (10)0.0025 (2)
C(8)0.0133 (2)0.0415 (4)0.0153 (2)0.0067 (2)0.0025 (2)0.0022 (2)
C(9)0.0189 (2)0.0332 (3)0.0155 (2)0.0105 (3)0.0028 (2)0.0008 (2)
C(10)0.0185 (2)0.0200 (2)0.0148 (2)0.0061 (2)0.0018 (2)0.0022 (2)
C(11)0.0123 (2)0.0145 (2)0.01110 (10)0.00160 (10)0.00080 (10)0.00060 (10)
C(12)0.01150 (10)0.01060 (10)0.00960 (10)0.00060 (10)0.00030 (10)0.00020 (10)
C(13)0.0149 (2)0.0140 (2)0.01020 (10)0.00030 (10)0.00150 (10)0.00020 (10)
C(14)0.0139 (2)0.0170 (2)0.01450 (10)0.0001 (2)0.00270 (10)0.00050 (10)
C(15)0.0135 (2)0.0224 (2)0.0191 (2)0.0062 (2)0.0009 (2)0.0012 (2)
C(16)0.0128 (2)0.0176 (2)0.0143 (2)0.0020 (2)0.00220 (10)0.0006 (2)
C(17)0.0139 (2)0.0208 (2)0.0176 (2)0.0012 (2)0.0037 (2)0.0013 (2)
C(18)0.0191 (2)0.0209 (2)0.0156 (2)0.0034 (2)0.0052 (2)0.0015 (2)
C(19)0.0168 (2)0.0123 (2)0.00960 (10)0.00020 (10)0.00070 (10)0.00060 (10)
C(20)0.0193 (2)0.0126 (2)0.0145 (2)0.0028 (2)0.0026 (2)0.00180 (10)
C(21)0.0150 (2)0.0162 (2)0.01280 (10)0.0057 (2)0.00210 (10)0.00040 (10)
Geometric parameters (Å, º) top
O(18)—C(18)1.4324 (9)C(9)—H(9)1.0801 (7)
O(18)—C(19)1.4282 (8)C(10)—C(11)1.3890 (8)
O(21)—C(21)1.2305 (9)C(10)—H(10)1.0831 (7)
N(5)—C(5)1.4867 (7)C(11)—C(12)1.5039 (7)
N(5)—C(6)1.4147 (7)C(12)—C(13)1.5433 (6)
N(5)—C(21)1.3721 (7)C(13)—C(14)1.5259 (8)
N(14)—C(1)1.4936 (8)C(13)—H(13A)1.0735 (5)
N(14)—C(14)1.4752 (8)C(13)—H(13B)1.0723 (5)
N(14)—C(15)1.4689 (8)C(14)—H(14A)1.0723 (5)
C(1)—C(2)1.5210 (7)C(14)—H(14B)1.0735 (6)
C(1)—C(12)1.5459 (6)C(15)—C(16)1.5057 (8)
C(1)—H(1)1.0704 (5)C(15)—H(15A)1.0743 (7)
C(2)—C(3)1.5344 (7)C(15)—H(15B)1.0732 (7)
C(2)—H(2A)1.0721 (5)C(16)—C(17)1.3404 (8)
C(2)—H(2B)1.0741 (6)C(17)—C(18)1.5060 (9)
C(3)—C(4)1.5369 (7)C(17)—H(17)1.0674 (7)
C(3)—C(16)1.5218 (8)C(18)—H(18A)1.0739 (7)
C(3)—H(3)1.0693 (4)C(18)—H(18B)1.0726 (6)
C(4)—C(5)1.5344 (6)C(19)—C(20)1.5458 (8)
C(4)—C(19)1.5358 (6)C(19)—H(19)1.0691 (5)
C(4)—H(4)1.0702 (5)C(20)—C(21)1.5163 (8)
C(5)—C(12)1.5569 (6)C(20)—H(20A)1.0726 (5)
C(5)—H(5)1.0714 (5)C(20)—H(20B)1.0724 (6)
C(6)—C(7)1.3966 (8)H(2A)—H(2B)1.7478
C(6)—C(11)1.4003 (7)H(13A)—H(13B)1.6953
C(7)—C(8)1.4024 (11)H(14A)—H(14B)1.7203
C(7)—H(7)1.0854 (8)H(15A)—H(15B)1.7630
C(8)—C(9)1.3961 (13)H(18A)—H(18B)1.6913
C(8)—H(8)1.0818 (7)H(20A)—H(20B)1.6952
C(9)—C(10)1.3980 (10)
C(18)—O(18)—C(19)114.46 (5)C(5)—C(12)—C(13)111.37 (4)
C(5)—N(5)—C(6)109.68 (4)C(11)—C(12)—C(13)112.32 (4)
C(5)—N(5)—C(21)118.73 (5)C(12)—C(13)—C(14)102.31 (4)
C(6)—N(5)—C(21)124.46 (5)C(12)—C(13)—H(13A)109.38 (4)
C(1)—N(14)—C(14)108.53 (5)C(12)—C(13)—H(13B)112.53 (4)
C(1)—N(14)—C(15)113.60 (5)C(14)—C(13)—H(13A)112.38 (5)
C(14)—N(14)—C(15)113.29 (5)C(14)—C(13)—H(13B)115.95 (5)
N(14)—C(1)—C(2)111.63 (5)H(13A)—C(13)—H(13B)104.38 (4)
N(14)—C(1)—C(12)105.52 (4)N(14)—C(14)—C(13)104.19 (5)
N(14)—C(1)—H(1)110.05 (4)N(14)—C(14)—H(14A)112.72 (5)
C(2)—C(1)—C(12)114.18 (4)N(14)—C(14)—H(14B)107.47 (5)
C(2)—C(1)—H(1)109.23 (4)C(13)—C(14)—H(14A)113.34 (5)
C(12)—C(1)—H(1)106.02 (4)C(13)—C(14)—H(14B)112.50 (5)
C(1)—C(2)—C(3)108.68 (4)H(14A)—C(14)—H(14B)106.59 (5)
C(1)—C(2)—H(2A)110.66 (5)N(14)—C(15)—C(16)111.18 (5)
C(1)—C(2)—H(2B)107.87 (5)N(14)—C(15)—H(15A)106.32 (5)
C(3)—C(2)—H(2A)109.54 (5)N(14)—C(15)—H(15B)108.25 (6)
C(3)—C(2)—H(2B)111.03 (5)C(16)—C(15)—H(15A)110.66 (6)
H(2A)—C(2)—H(2B)109.05 (4)C(16)—C(15)—H(15B)109.99 (5)
C(2)—C(3)—C(4)106.34 (4)H(15A)—C(15)—H(15B)110.36 (5)
C(2)—C(3)—C(16)108.83 (4)C(3)—C(16)—C(15)114.77 (5)
C(2)—C(3)—H(3)108.85 (4)C(3)—C(16)—C(17)122.25 (5)
C(4)—C(3)—C(16)114.78 (4)C(15)—C(16)—C(17)122.90 (6)
C(4)—C(3)—H(3)109.59 (4)C(16)—C(17)—C(18)121.84 (6)
C(16)—C(3)—H(3)108.31 (4)C(16)—C(17)—H(17)118.68 (6)
C(3)—C(4)—C(5)113.28 (4)C(18)—C(17)—H(17)119.47 (6)
C(3)—C(4)—C(19)118.46 (4)O(18)—C(18)—C(17)111.37 (5)
C(3)—C(4)—H(4)105.27 (4)O(18)—C(18)—H(18A)110.26 (6)
C(5)—C(4)—C(19)107.82 (4)O(18)—C(18)—H(18B)106.91 (6)
C(5)—C(4)—H(4)103.69 (4)C(17)—C(18)—H(18A)112.89 (6)
C(19)—C(4)—H(4)107.08 (4)C(17)—C(18)—H(18B)111.02 (6)
N(5)—C(5)—C(4)106.22 (4)H(18A)—C(18)—H(18B)103.99 (5)
N(5)—C(5)—C(12)104.67 (4)O(18)—C(19)—C(4)114.65 (5)
N(5)—C(5)—H(5)109.33 (4)O(18)—C(19)—C(20)104.95 (5)
C(4)—C(5)—C(12)116.94 (4)O(18)—C(19)—H(19)107.25 (5)
C(4)—C(5)—H(5)110.18 (4)C(4)—C(19)—C(20)109.72 (4)
C(12)—C(5)—H(5)109.14 (4)C(4)—C(19)—H(19)108.45 (4)
N(5)—C(6)—C(7)129.34 (6)C(20)—C(19)—H(19)111.82 (4)
N(5)—C(6)—C(11)109.50 (5)C(19)—C(20)—C(21)116.56 (4)
C(7)—C(6)—C(11)121.16 (6)C(19)—C(20)—H(20A)110.67 (5)
C(6)—C(7)—C(8)117.62 (7)C(19)—C(20)—H(20B)105.37 (5)
C(6)—C(7)—H(7)120.76 (7)C(21)—C(20)—H(20A)109.78 (5)
C(8)—C(7)—H(7)121.60 (6)C(21)—C(20)—H(20B)109.24 (5)
C(7)—C(8)—C(9)121.61 (6)H(20A)—C(20)—H(20B)104.44 (5)
C(7)—C(8)—H(8)117.24 (9)O(21)—C(21)—N(5)122.44 (7)
C(9)—C(8)—H(8)121.15 (8)O(21)—C(21)—C(20)122.71 (6)
C(8)—C(9)—C(10)119.85 (7)N(5)—C(21)—C(20)114.84 (5)
C(8)—C(9)—H(9)120.44 (8)C(2)—H(2A)—H(2B)35.51 (3)
C(10)—C(9)—H(9)119.71 (9)C(2)—H(2B)—H(2A)35.44 (3)
C(9)—C(10)—C(11)119.27 (7)C(13)—H(13A)—H(13B)37.79 (3)
C(9)—C(10)—H(10)120.38 (6)C(13)—H(13B)—H(13A)37.83 (3)
C(11)—C(10)—H(10)120.35 (6)C(14)—H(14A)—H(14B)36.73 (3)
C(6)—C(11)—C(10)120.45 (5)C(14)—H(14B)—H(14A)36.68 (3)
C(6)—C(11)—C(12)110.73 (4)C(15)—H(15A)—H(15B)34.80 (3)
C(10)—C(11)—C(12)128.66 (5)C(15)—H(15B)—H(15A)34.84 (3)
C(1)—C(12)—C(5)114.30 (4)C(18)—H(18A)—H(18B)37.98 (3)
C(1)—C(12)—C(11)116.60 (4)C(18)—H(18B)—H(18A)38.03 (3)
C(1)—C(12)—C(13)100.09 (4)C(20)—H(20A)—H(20B)37.78 (3)
C(5)—C(12)—C(11)102.55 (4)C(20)—H(20B)—H(20A)37.79 (3)
(IV) Strychnine top
Crystal data top
C21H22N2O2F(000) = 712
Mr = 334.41Mo Kα radiation, λ = 0.53 Å
Orthorhombic, P212121Cell parameters from 8611 reflections
Hall symbol: P 2ac 2abθ = 2.4–37.7°
a = 11.326 (1) ŵ = 0.05 mm1
b = 11.765 (1) ÅT = 25 K
c = 11.994 (1) Å, colorless
V = 1598.23 Å3 × × mm
Z = 4
Data collection top
Si double crystal monochromatork = ??
h = ??l = ??
Refinement top
Refinement on F922 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.02 w1 = 1/[s2(Fo)]
wR(F2) = 0.021(Δ/σ)max = 0.069
S = 1.21Δρmax = 0.28 e Å3
9466 reflectionsΔρmin = 0.20 e Å3
Crystal data top
C21H22N2O2V = 1598.23 Å3
Mr = 334.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.326 (1) ŵ = 0.05 mm1
b = 11.765 (1) ÅT = 25 K
c = 11.994 (1) Å × × mm
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.02922 parameters
wR(F2) = 0.0210 restraints
S = 1.21Δρmax = 0.28 e Å3
9466 reflectionsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(18)0.46248 (3)0.01413 (3)1.00094 (3)0.007
O(21)0.86981 (3)0.00873 (4)0.91689 (4)0.01
N(5)0.72505 (3)0.08409 (3)0.82040 (3)0.006
N(14)0.39481 (3)0.29346 (3)0.73327 (3)0.007
C(1)0.51621 (3)0.32496 (3)0.77095 (3)0.006
C(2)0.51925 (3)0.35316 (3)0.89498 (3)0.007
C(3)0.47947 (3)0.24781 (3)0.96088 (3)0.006
C(4)0.57776 (3)0.15854 (3)0.94728 (3)0.005
C(5)0.60106 (3)0.12587 (3)0.82498 (3)0.005
C(6)0.79610 (3)0.16338 (3)0.76201 (3)0.006
C(7)0.91828 (3)0.16285 (3)0.74512 (3)0.008
C(8)0.96745 (3)0.25393 (4)0.68538 (3)0.01
C(9)0.89720 (3)0.34216 (4)0.64361 (3)0.009
C(10)0.77455 (3)0.33933 (3)0.65887 (3)0.008
C(11)0.72463 (3)0.24964 (3)0.71815 (3)0.006
C(12)0.59600 (3)0.22360 (3)0.73717 (3)0.005
C(13)0.53274 (3)0.18501 (3)0.62930 (3)0.007
C(14)0.40285 (3)0.19036 (3)0.66316 (3)0.007
C(15)0.30929 (3)0.28265 (3)0.82496 (3)0.008
C(16)0.35852 (3)0.21058 (3)0.91844 (3)0.007
C(17)0.30377 (3)0.11751 (3)0.95740 (3)0.008
C(18)0.35959 (3)0.04162 (3)1.04419 (3)0.008
C(19)0.57002 (3)0.04793 (3)1.01543 (3)0.006
C(20)0.66872 (3)0.03483 (3)0.97829 (3)0.007
C(21)0.76471 (3)0.01430 (3)0.90438 (3)0.006
H(1)0.544960.397520.724680.023 (5)
H(2A)0.463360.42380.914910.032 (5)
H(2B)0.608150.376890.915820.020 (5)
H(3)0.472330.270071.047010.015 (4)
H(4)0.656160.202210.972940.024 (4)
H(5)0.544240.058220.799070.012 (3)
H(7)0.974910.095870.776620.026 (5)
H(8)1.062060.253960.671250.022 (5)
H(9)0.936650.412380.598650.014 (4)
H(10)0.7190.405050.623550.032 (5)
H(13A)0.55250.243370.563170.021 (5)
H(13B)0.563050.104190.599720.027 (5)
H(14A)0.34430.194980.592960.014 (4)
H(14B)0.379580.117860.71260.028 (5)
H(15A)0.230520.243650.793050.036 (6)
H(15B)0.287620.365920.854840.033 (5)
H(17)0.218860.096850.923710.019 (4)
H(18A)0.38190.086811.11890.019 (5)
H(18B)0.299880.024591.068630.018 (5)
H(19)0.575930.069691.101840.022 (4)
H(20A)0.705920.07481.050560.034 (6)
H(20B)0.625770.09960.930210.020 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(18)0.00673 (9)0.00637 (8)0.00816 (10)0.00059 (7)0.00034 (8)0.00012 (10)
O(21)0.00650 (10)0.01260 (10)0.01010 (10)0.00340 (10)0.00060 (10)0.00270 (10)
N(5)0.00523 (8)0.00652 (8)0.00558 (9)0.00135 (7)0.00034 (7)0.00129 (9)
N(14)0.00573 (8)0.00747 (9)0.00649 (9)0.00100 (7)0.00005 (7)0.00012 (10)
C(1)0.00665 (9)0.00503 (8)0.00580 (9)0.00048 (7)0.00016 (7)0.00020 (9)
C(2)0.00830 (10)0.00520 (10)0.00630 (10)0.00030 (10)0.00010 (10)0.00060 (10)
C(3)0.00657 (9)0.00577 (8)0.00541 (9)0.00051 (7)0.00042 (7)0.00023 (9)
C(4)0.00578 (8)0.00515 (8)0.00529 (9)0.00035 (7)0.00001 (7)0.00022 (9)
C(5)0.00526 (8)0.00512 (8)0.00465 (8)0.00032 (7)0.00011 (7)0.00039 (9)
C(6)0.00492 (8)0.00748 (9)0.00599 (9)0.00047 (7)0.00065 (7)0.00058 (10)
C(7)0.00543 (9)0.01169 (11)0.00782 (10)0.00075 (8)0.00077 (8)0.00046 (11)
C(8)0.00610 (10)0.01420 (10)0.00850 (10)0.00150 (10)0.00110 (10)0.00070 (10)
C(9)0.00780 (10)0.01140 (10)0.00860 (10)0.00280 (10)0.00130 (10)0.00130 (10)
C(10)0.00736 (9)0.00814 (10)0.00806 (10)0.00144 (8)0.00085 (8)0.00188 (10)
C(11)0.00534 (8)0.00641 (8)0.00612 (9)0.00048 (7)0.00044 (7)0.00110 (9)
C(12)0.00511 (8)0.00506 (8)0.00513 (9)0.00024 (6)0.00017 (7)0.00005 (9)
C(13)0.00686 (9)0.00727 (9)0.00538 (9)0.00022 (7)0.00045 (7)0.00059 (10)
C(14)0.00649 (9)0.00806 (10)0.00739 (10)0.00025 (8)0.00097 (8)0.00096 (10)
C(15)0.00584 (9)0.00912 (10)0.00775 (10)0.00177 (8)0.00048 (8)0.00062 (11)
C(16)0.00591 (9)0.00725 (9)0.00654 (10)0.00053 (7)0.00045 (7)0.00040 (10)
C(17)0.00633 (9)0.00823 (10)0.00800 (11)0.00050 (8)0.00047 (8)0.00061 (10)
C(18)0.00790 (10)0.00880 (10)0.00750 (10)0.00050 (10)0.00150 (10)0.00100 (10)
C(19)0.00673 (9)0.00591 (9)0.00522 (9)0.00019 (7)0.00024 (7)0.00034 (9)
C(20)0.00773 (9)0.00608 (9)0.00745 (10)0.00117 (7)0.00034 (8)0.00111 (10)
C(21)0.00609 (9)0.00674 (9)0.00625 (10)0.00165 (7)0.00030 (7)0.00077 (10)
Geometric parameters (Å, º) top
O(18)—C(18)1.4335 (5)C(9)—H(9)1.0840 (4)
O(18)—C(19)1.4297 (5)C(10)—C(11)1.3936 (5)
O(21)—C(21)1.2284 (5)C(10)—H(10)1.0836 (4)
N(5)—C(5)1.4872 (4)C(11)—C(12)1.5042 (4)
N(5)—C(6)1.4178 (5)C(12)—C(13)1.5475 (5)
N(5)—C(21)1.3761 (5)C(13)—C(14)1.5254 (5)
N(14)—C(1)1.4924 (5)C(13)—H(13A)1.0738 (4)
N(14)—C(14)1.4808 (5)C(13)—H(13B)1.0728 (3)
N(14)—C(15)1.4705 (5)C(14)—H(14A)1.0729 (4)
C(1)—C(2)1.5255 (5)C(14)—H(14B)1.0732 (4)
C(1)—C(12)1.5509 (4)C(15)—C(16)1.5133 (5)
C(1)—H(1)1.0703 (3)C(15)—H(15A)1.0731 (4)
C(2)—C(3)1.5393 (5)C(15)—H(15B)1.0733 (4)
C(2)—H(2A)1.0724 (3)C(16)—C(17)1.3436 (5)
C(2)—H(2B)1.0731 (3)C(17)—C(18)1.5111 (5)
C(3)—C(4)1.5392 (4)C(17)—H(17)1.0700 (4)
C(3)—C(16)1.5240 (5)C(18)—H(18A)1.0730 (4)
C(3)—H(3)1.0696 (3)C(18)—H(18B)1.0729 (4)
C(4)—C(5)1.5403 (5)C(19)—C(20)1.5478 (5)
C(4)—C(19)1.5414 (5)C(19)—H(19)1.0705 (4)
C(4)—H(4)1.0704 (3)C(20)—C(21)1.5167 (5)
C(5)—C(12)1.5623 (4)C(20)—H(20A)1.0729 (4)
C(5)—H(5)1.0701 (3)C(20)—H(20B)1.0732 (4)
C(6)—C(7)1.3965 (4)H(2A)—H(2B)1.7283
C(6)—C(11)1.4014 (5)H(13A)—H(13B)1.7022
C(7)—C(8)1.4055 (6)H(14A)—H(14B)1.7457
C(7)—H(7)1.0845 (4)H(15A)—H(15B)1.7446
C(8)—C(9)1.4014 (6)H(18A)—H(18B)1.7171
C(8)—H(8)1.0832 (4)H(20A)—H(20B)1.7302
C(9)—C(10)1.3994 (5)
C(18)—O(18)—C(19)114.32 (3)C(5)—C(12)—C(13)111.38 (3)
C(5)—N(5)—C(6)109.53 (3)C(11)—C(12)—C(13)112.34 (3)
C(5)—N(5)—C(21)118.56 (3)C(12)—C(13)—C(14)102.13 (3)
C(6)—N(5)—C(21)124.85 (3)C(12)—C(13)—H(13A)109.51 (3)
C(1)—N(14)—C(14)108.66 (3)C(12)—C(13)—H(13B)112.97 (3)
C(1)—N(14)—C(15)113.56 (3)C(14)—C(13)—H(13A)111.76 (3)
C(14)—N(14)—C(15)113.24 (3)C(14)—C(13)—H(13B)115.63 (3)
N(14)—C(1)—C(2)111.75 (3)H(13A)—C(13)—H(13B)104.93 (3)
N(14)—C(1)—C(12)105.33 (3)N(14)—C(14)—C(13)104.15 (3)
N(14)—C(1)—H(1)108.72 (3)N(14)—C(14)—H(14A)111.52 (3)
C(2)—C(1)—C(12)114.19 (3)N(14)—C(14)—H(14B)108.91 (3)
C(2)—C(1)—H(1)108.99 (3)C(13)—C(14)—H(14A)112.78 (3)
C(12)—C(1)—H(1)107.64 (3)C(13)—C(14)—H(14B)110.52 (3)
C(1)—C(2)—C(3)108.60 (3)H(14A)—C(14)—H(14B)108.87 (3)
C(1)—C(2)—H(2A)111.93 (3)N(14)—C(15)—C(16)111.19 (3)
C(1)—C(2)—H(2B)107.78 (3)N(14)—C(15)—H(15A)108.42 (3)
C(3)—C(2)—H(2A)109.84 (3)N(14)—C(15)—H(15B)108.73 (3)
C(3)—C(2)—H(2B)111.36 (3)C(16)—C(15)—H(15A)109.25 (3)
H(2A)—C(2)—H(2B)107.33 (3)C(16)—C(15)—H(15B)110.45 (3)
C(2)—C(3)—C(4)106.61 (3)H(15A)—C(15)—H(15B)108.75 (3)
C(2)—C(3)—C(16)108.83 (3)C(3)—C(16)—C(15)114.61 (3)
C(2)—C(3)—H(3)108.71 (3)C(3)—C(16)—C(17)122.16 (3)
C(4)—C(3)—C(16)114.58 (3)C(15)—C(16)—C(17)123.14 (3)
C(4)—C(3)—H(3)108.95 (3)C(16)—C(17)—C(18)122.05 (3)
C(16)—C(3)—H(3)109.02 (3)C(16)—C(17)—H(17)117.89 (3)
C(3)—C(4)—C(5)113.29 (3)C(18)—C(17)—H(17)120.05 (3)
C(3)—C(4)—C(19)118.74 (3)O(18)—C(18)—C(17)111.15 (3)
C(3)—C(4)—H(4)103.82 (3)O(18)—C(18)—H(18A)109.84 (3)
C(5)—C(4)—C(19)107.70 (3)O(18)—C(18)—H(18B)106.05 (3)
C(5)—C(4)—H(4)104.64 (3)C(17)—C(18)—H(18A)112.36 (3)
C(19)—C(4)—H(4)107.52 (3)C(17)—C(18)—H(18B)110.86 (3)
N(5)—C(5)—C(4)106.21 (3)H(18A)—C(18)—H(18B)106.29 (3)
N(5)—C(5)—C(12)104.70 (2)O(18)—C(19)—C(4)114.61 (3)
N(5)—C(5)—H(5)107.98 (3)O(18)—C(19)—C(20)104.84 (3)
C(4)—C(5)—C(12)116.89 (3)O(18)—C(19)—H(19)107.07 (3)
C(4)—C(5)—H(5)111.13 (3)C(4)—C(19)—C(20)109.82 (3)
C(12)—C(5)—H(5)109.35 (3)C(4)—C(19)—H(19)107.93 (3)
N(5)—C(6)—C(7)129.01 (3)C(20)—C(19)—H(19)112.64 (3)
N(5)—C(6)—C(11)109.70 (3)C(19)—C(20)—C(21)116.36 (3)
C(7)—C(6)—C(11)121.29 (3)C(19)—C(20)—H(20A)109.07 (3)
C(6)—C(7)—C(8)117.52 (3)C(19)—C(20)—H(20B)106.06 (3)
C(6)—C(7)—H(7)122.47 (4)C(21)—C(20)—H(20A)111.09 (3)
C(8)—C(7)—H(7)120.01 (3)C(21)—C(20)—H(20B)106.32 (3)
C(7)—C(8)—C(9)121.66 (3)H(20A)—C(20)—H(20B)107.45 (3)
C(7)—C(8)—H(8)118.10 (4)O(21)—C(21)—N(5)122.48 (4)
C(9)—C(8)—H(8)120.24 (4)O(21)—C(21)—C(20)122.46 (3)
C(8)—C(9)—C(10)119.83 (3)N(5)—C(21)—C(20)115.04 (3)
C(8)—C(9)—H(9)120.75 (3)C(2)—H(2A)—H(2B)36.351 (18)
C(10)—C(9)—H(9)119.42 (4)C(2)—H(2B)—H(2A)36.322 (17)
C(9)—C(10)—C(11)119.10 (3)C(13)—H(13A)—H(13B)37.514 (18)
C(9)—C(10)—H(10)120.42 (3)C(13)—H(13B)—H(13A)37.554 (19)
C(11)—C(10)—H(10)120.46 (3)C(14)—H(14A)—H(14B)35.572 (19)
C(6)—C(11)—C(10)120.56 (3)C(14)—H(14B)—H(14A)35.563 (19)
C(6)—C(11)—C(12)110.65 (3)C(15)—H(15A)—H(15B)35.632 (19)
C(10)—C(11)—C(12)128.61 (3)C(15)—H(15B)—H(15A)35.622 (18)
C(1)—C(12)—C(5)114.38 (3)C(18)—H(18A)—H(18B)36.853 (19)
C(1)—C(12)—C(11)116.43 (3)C(18)—H(18B)—H(18A)36.86 (2)
C(1)—C(12)—C(13)100.15 (2)C(20)—H(20A)—H(20B)36.283 (19)
C(5)—C(12)—C(11)102.56 (2)C(20)—H(20B)—H(20A)36.270 (19)

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC21H22N2O2C21H22N2O2C21H22N2O2C21H22N2O2
Mr334.41334.41334.41334.41
Crystal system, space groupOrthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121
Temperature (K)1002510025
a, b, c (Å)11.309 (1), 11.785 (1), 12.002 (1)11.326 (1), 11.765 (1), 11.994 (1)11.309 (1), 11.785 (1), 12.002 (1)11.326 (1), 11.765 (1), 11.994 (1)
V3)1599.651598.231599.651598.23
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.05
Crystal size (mm) × × × × × × × ×
Data collection
Diffractometer????
Absorption correction
No. of measured, independent and
observed (?) reflections
?, ?, ? ?, ?, ? ?, ?, ? ?, ?, ?
Rint????
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.018, 0.47 0.017, 0.018, 0.93 0.023, 0.016, 0.69 0.02, 0.021, 1.21
No. of reflections8480943081929466
No. of parameters922922922922
(Δ/σ)max0.1990.0030.0070.069
Δρmax, Δρmin (e Å3)0.16, 0.120.19, 0.110.16, 0.140.28, 0.20

Computer programs: Koritsanszky et al., (2003).

Selected geometric parameters (Å, º) for (I) top
O(18)—C(18)1.4328 (7)C(9)—H(9)1.0803 (6)
O(18)—C(19)1.4305 (6)C(10)—C(11)1.3897 (6)
O(21)—C(21)1.2309 (6)C(10)—H(10)1.0820 (6)
N(5)—C(5)1.4873 (5)C(11)—C(12)1.5039 (5)
N(5)—C(6)1.4158 (6)C(12)—C(13)1.5444 (5)
N(5)—C(21)1.3725 (5)C(13)—C(14)1.5255 (6)
N(14)—C(1)1.4935 (6)C(13)—H(13A)1.0735 (4)
N(14)—C(14)1.4760 (6)C(13)—H(13B)1.0729 (4)
N(14)—C(15)1.4688 (6)C(14)—H(14A)1.0720 (4)
C(1)—C(2)1.5229 (5)C(14)—H(14B)1.0741 (5)
C(1)—C(12)1.5467 (5)C(15)—C(16)1.5083 (7)
C(1)—H(1)1.0693 (4)C(15)—H(15A)1.0733 (5)
C(2)—C(3)1.5343 (6)C(15)—H(15B)1.0738 (5)
C(2)—H(2A)1.0728 (4)C(16)—C(17)1.3403 (7)
C(2)—H(2B)1.0738 (5)C(17)—C(18)1.5062 (7)
C(3)—C(4)1.5376 (5)C(17)—H(17)1.0677 (5)
C(3)—C(16)1.5237 (6)C(18)—H(18A)1.0729 (5)
C(3)—H(3)1.0691 (4)C(18)—H(18B)1.0726 (5)
C(4)—C(5)1.5356 (5)C(19)—C(20)1.5455 (6)
C(4)—C(19)1.5358 (5)C(19)—H(19)1.0693 (4)
C(4)—H(4)1.0704 (4)C(20)—C(21)1.5157 (7)
C(5)—C(12)1.5564 (5)C(20)—H(20A)1.0715 (4)
C(5)—H(5)1.0714 (4)C(20)—H(20B)1.0724 (5)
C(6)—C(7)1.3968 (6)H(2A)—H(2B)1.7527
C(6)—C(11)1.4012 (6)H(13A)—H(13B)1.7000
C(7)—C(8)1.4030 (9)H(14A)—H(14B)1.7498
C(7)—H(7)1.0846 (6)H(15A)—H(15B)1.7429
C(8)—C(9)1.3986 (10)H(18A)—H(18B)1.6871
C(8)—H(8)1.0828 (5)H(20A)—H(20B)1.7443
C(9)—C(10)1.3977 (8)
C(18)—O(18)—C(19)114.43 (4)C(5)—C(12)—C(13)111.38 (3)
C(5)—N(5)—C(6)109.61 (3)C(11)—C(12)—C(13)112.28 (3)
C(5)—N(5)—C(21)118.68 (4)C(12)—C(13)—C(14)102.25 (3)
C(6)—N(5)—C(21)124.52 (4)C(12)—C(13)—H(13A)109.55 (3)
C(1)—N(14)—C(14)108.50 (3)C(12)—C(13)—H(13B)112.13 (3)
C(1)—N(14)—C(15)113.69 (4)C(14)—C(13)—H(13A)112.27 (4)
C(14)—N(14)—C(15)113.29 (4)C(14)—C(13)—H(13B)115.97 (4)
N(14)—C(1)—C(2)111.59 (4)H(13A)—C(13)—H(13B)104.75 (3)
N(14)—C(1)—C(12)105.50 (3)N(14)—C(14)—C(13)104.24 (4)
N(14)—C(1)—H(1)110.71 (3)N(14)—C(14)—H(14A)110.99 (4)
C(2)—C(1)—C(12)114.10 (3)N(14)—C(14)—H(14B)107.71 (4)
C(2)—C(1)—H(1)108.56 (3)C(13)—C(14)—H(14A)113.62 (4)
C(12)—C(1)—H(1)106.25 (3)C(13)—C(14)—H(14B)110.82 (4)
C(1)—C(2)—C(3)108.70 (3)H(14A)—C(14)—H(14B)109.24 (4)
C(1)—C(2)—H(2A)109.68 (4)N(14)—C(15)—C(16)111.15 (4)
C(1)—C(2)—H(2B)106.60 (4)N(14)—C(15)—H(15A)105.43 (4)
C(3)—C(2)—H(2A)110.42 (4)N(14)—C(15)—H(15B)108.66 (5)
C(3)—C(2)—H(2B)111.86 (4)C(16)—C(15)—H(15A)110.80 (5)
H(2A)—C(2)—H(2B)109.48 (3)C(16)—C(15)—H(15B)112.02 (4)
C(2)—C(3)—C(4)106.42 (3)H(15A)—C(15)—H(15B)108.53 (4)
C(2)—C(3)—C(16)108.86 (3)C(3)—C(16)—C(15)114.68 (4)
C(2)—C(3)—H(3)109.75 (3)C(3)—C(16)—C(17)122.25 (4)
C(4)—C(3)—C(16)114.69 (3)C(15)—C(16)—C(17)122.98 (5)
C(4)—C(3)—H(3)110.44 (3)C(16)—C(17)—C(18)121.89 (4)
C(16)—C(3)—H(3)106.64 (3)C(16)—C(17)—H(17)117.75 (5)
C(3)—C(4)—C(5)113.26 (3)C(18)—C(17)—H(17)120.33 (5)
C(3)—C(4)—C(19)118.56 (3)O(18)—C(18)—C(17)111.27 (4)
C(3)—C(4)—H(4)104.05 (3)O(18)—C(18)—H(18A)109.95 (5)
C(5)—C(4)—C(19)107.83 (3)O(18)—C(18)—H(18B)107.18 (5)
C(5)—C(4)—H(4)104.10 (3)C(17)—C(18)—H(18A)112.80 (5)
C(19)—C(4)—H(4)107.89 (3)C(17)—C(18)—H(18B)111.56 (5)
N(5)—C(5)—C(4)106.20 (3)H(18A)—C(18)—H(18B)103.68 (4)
N(5)—C(5)—C(12)104.71 (3)O(18)—C(19)—C(4)114.60 (4)
N(5)—C(5)—H(5)108.24 (3)O(18)—C(19)—C(20)104.91 (4)
C(4)—C(5)—C(12)116.94 (3)O(18)—C(19)—H(19)106.37 (4)
C(4)—C(5)—H(5)110.80 (3)C(4)—C(19)—C(20)109.79 (3)
C(12)—C(5)—H(5)109.42 (3)C(4)—C(19)—H(19)109.60 (3)
N(5)—C(6)—C(7)129.25 (5)C(20)—C(19)—H(19)111.49 (3)
N(5)—C(6)—C(11)109.51 (3)C(19)—C(20)—C(21)116.46 (3)
C(7)—C(6)—C(11)121.24 (4)C(19)—C(20)—H(20A)110.41 (4)
C(6)—C(7)—C(8)117.54 (5)C(19)—C(20)—H(20B)105.25 (4)
C(6)—C(7)—H(7)121.07 (5)C(21)—C(20)—H(20A)108.43 (4)
C(8)—C(7)—H(7)121.30 (5)C(21)—C(20)—H(20B)107.10 (4)
C(7)—C(8)—C(9)121.65 (5)H(20A)—C(20)—H(20B)108.90 (4)
C(7)—C(8)—H(8)116.16 (7)O(21)—C(21)—N(5)122.40 (5)
C(9)—C(8)—H(8)122.19 (6)O(21)—C(21)—C(20)122.68 (5)
C(8)—C(9)—C(10)119.81 (5)N(5)—C(21)—C(20)114.91 (4)
C(8)—C(9)—H(9)119.11 (5)C(2)—H(2A)—H(2B)35.28 (2)
C(10)—C(9)—H(9)121.08 (7)C(2)—H(2B)—H(2A)35.24 (2)
C(9)—C(10)—C(11)119.29 (5)C(13)—H(13A)—H(13B)37.61 (2)
C(9)—C(10)—H(10)120.69 (5)C(13)—H(13B)—H(13A)37.64 (2)
C(11)—C(10)—H(10)120.02 (4)C(14)—H(14A)—H(14B)35.42 (3)
C(6)—C(11)—C(10)120.42 (4)C(14)—H(14B)—H(14A)35.34 (2)
C(6)—C(11)—C(12)110.70 (3)C(15)—H(15A)—H(15B)35.75 (3)
C(10)—C(11)—C(12)128.71 (4)C(15)—H(15B)—H(15A)35.73 (3)
C(1)—C(12)—C(5)114.40 (3)C(18)—H(18A)—H(18B)38.15 (3)
C(1)—C(12)—C(11)116.51 (3)C(18)—H(18B)—H(18A)38.16 (3)
C(1)—C(12)—C(13)100.06 (3)C(20)—H(20A)—H(20B)35.57 (2)
C(5)—C(12)—C(11)102.60 (3)C(20)—H(20B)—H(20A)35.53 (2)
Selected geometric parameters (Å, º) for (II) top
O(18)—C(18)1.4338 (6)C(9)—H(9)1.0827 (5)
O(18)—C(19)1.4319 (5)C(10)—C(11)1.3896 (5)
O(21)—C(21)1.2301 (6)C(10)—H(10)1.0840 (5)
N(5)—C(5)1.4891 (5)C(11)—C(12)1.5076 (5)
N(5)—C(6)1.4156 (5)C(12)—C(13)1.5452 (5)
N(5)—C(21)1.3747 (5)C(13)—C(14)1.5288 (5)
N(14)—C(1)1.4952 (5)C(13)—H(13A)1.0740 (4)
N(14)—C(14)1.4766 (5)C(13)—H(13B)1.0722 (4)
N(14)—C(15)1.4715 (5)C(14)—H(14A)1.0733 (4)
C(1)—C(2)1.5238 (5)C(14)—H(14B)1.0737 (4)
C(1)—C(12)1.5477 (5)C(15)—C(16)1.5098 (6)
C(1)—H(1)1.0703 (4)C(15)—H(15A)1.0735 (4)
C(2)—C(3)1.5359 (5)C(15)—H(15B)1.0729 (4)
C(2)—H(2A)1.0725 (4)C(16)—C(17)1.3425 (6)
C(2)—H(2B)1.0734 (4)C(17)—C(18)1.5083 (6)
C(3)—C(4)1.5385 (5)C(17)—H(17)1.0689 (4)
C(3)—C(16)1.5238 (5)C(18)—H(18A)1.0736 (4)
C(3)—H(3)1.0696 (3)C(18)—H(18B)1.0727 (4)
C(4)—C(5)1.5374 (5)C(19)—C(20)1.5470 (5)
C(4)—C(19)1.5374 (5)C(19)—H(19)1.0694 (4)
C(4)—H(4)1.0699 (4)C(20)—C(21)1.5175 (6)
C(5)—C(12)1.5579 (5)C(20)—H(20A)1.0726 (4)
C(5)—H(5)1.0715 (4)C(20)—H(20B)1.0727 (4)
C(6)—C(7)1.3996 (5)H(2A)—H(2B)1.7488
C(6)—C(11)1.4014 (5)H(13A)—H(13B)1.7085
C(7)—C(8)1.4036 (7)H(14A)—H(14B)1.7240
C(7)—H(7)1.0849 (5)H(15A)—H(15B)1.7563
C(8)—C(9)1.3991 (7)H(18A)—H(18B)1.7121
C(8)—H(8)1.0828 (4)H(20A)—H(20B)1.7234
C(9)—C(10)1.4014 (6)
C(18)—O(18)—C(19)114.50 (4)C(5)—C(12)—C(13)111.47 (3)
C(5)—N(5)—C(6)109.73 (3)C(11)—C(12)—C(13)112.27 (3)
C(5)—N(5)—C(21)118.62 (3)C(12)—C(13)—C(14)102.20 (3)
C(6)—N(5)—C(21)124.53 (3)C(12)—C(13)—H(13A)109.11 (3)
C(1)—N(14)—C(14)108.51 (3)C(12)—C(13)—H(13B)112.21 (3)
C(1)—N(14)—C(15)113.66 (3)C(14)—C(13)—H(13A)111.62 (3)
C(14)—N(14)—C(15)113.28 (4)C(14)—C(13)—H(13B)116.17 (3)
N(14)—C(1)—C(2)111.62 (3)H(13A)—C(13)—H(13B)105.52 (3)
N(14)—C(1)—C(12)105.52 (3)N(14)—C(14)—C(13)104.17 (3)
N(14)—C(1)—H(1)110.29 (3)N(14)—C(14)—H(14A)112.12 (3)
C(2)—C(1)—C(12)114.14 (3)N(14)—C(14)—H(14B)108.43 (3)
C(2)—C(1)—H(1)108.26 (3)C(13)—C(14)—H(14A)114.04 (3)
C(12)—C(1)—H(1)106.89 (3)C(13)—C(14)—H(14B)111.19 (3)
C(1)—C(2)—C(3)108.67 (3)H(14A)—C(14)—H(14B)106.83 (3)
C(1)—C(2)—H(2A)110.56 (3)N(14)—C(15)—C(16)111.07 (3)
C(1)—C(2)—H(2B)107.40 (3)N(14)—C(15)—H(15A)105.98 (4)
C(3)—C(2)—H(2A)108.51 (3)N(14)—C(15)—H(15B)108.00 (4)
C(3)—C(2)—H(2B)112.53 (3)C(16)—C(15)—H(15A)111.61 (4)
H(2A)—C(2)—H(2B)109.17 (3)C(16)—C(15)—H(15B)110.21 (4)
C(2)—C(3)—C(4)106.41 (3)H(15A)—C(15)—H(15B)109.82 (3)
C(2)—C(3)—C(16)108.84 (3)C(3)—C(16)—C(15)114.79 (3)
C(2)—C(3)—H(3)109.06 (3)C(3)—C(16)—C(17)122.28 (4)
C(4)—C(3)—C(16)114.80 (3)C(15)—C(16)—C(17)122.84 (4)
C(4)—C(3)—H(3)108.22 (3)C(16)—C(17)—C(18)121.77 (4)
C(16)—C(3)—H(3)109.38 (3)C(16)—C(17)—H(17)119.22 (4)
C(3)—C(4)—C(5)113.25 (3)C(18)—C(17)—H(17)118.98 (4)
C(3)—C(4)—C(19)118.57 (3)O(18)—C(18)—C(17)111.29 (3)
C(3)—C(4)—H(4)104.44 (3)O(18)—C(18)—H(18A)109.83 (4)
C(5)—C(4)—C(19)107.79 (3)O(18)—C(18)—H(18B)106.59 (4)
C(5)—C(4)—H(4)104.67 (3)C(17)—C(18)—H(18A)112.90 (4)
C(19)—C(4)—H(4)107.00 (3)C(17)—C(18)—H(18B)110.10 (4)
N(5)—C(5)—C(4)106.20 (3)H(18A)—C(18)—H(18B)105.82 (3)
N(5)—C(5)—C(12)104.65 (3)O(18)—C(19)—C(4)114.57 (3)
N(5)—C(5)—H(5)107.95 (3)O(18)—C(19)—C(20)105.03 (3)
C(4)—C(5)—C(12)116.95 (3)O(18)—C(19)—H(19)105.72 (3)
C(4)—C(5)—H(5)110.79 (3)C(4)—C(19)—C(20)109.72 (3)
C(12)—C(5)—H(5)109.71 (3)C(4)—C(19)—H(19)109.87 (3)
N(5)—C(6)—C(7)129.21 (4)C(20)—C(19)—H(19)111.84 (3)
N(5)—C(6)—C(11)109.52 (3)C(19)—C(20)—C(21)116.53 (3)
C(7)—C(6)—C(11)121.27 (4)C(19)—C(20)—H(20A)110.85 (3)
C(6)—C(7)—C(8)117.56 (4)C(19)—C(20)—H(20B)104.74 (3)
C(6)—C(7)—H(7)123.89 (4)C(21)—C(20)—H(20A)109.48 (3)
C(8)—C(7)—H(7)118.54 (4)C(21)—C(20)—H(20B)107.79 (3)
C(7)—C(8)—C(9)121.58 (4)H(20A)—C(20)—H(20B)106.90 (3)
C(7)—C(8)—H(8)117.22 (5)O(21)—C(21)—N(5)122.52 (4)
C(9)—C(8)—H(8)121.19 (5)O(21)—C(21)—C(20)122.66 (4)
C(8)—C(9)—C(10)119.85 (4)N(5)—C(21)—C(20)114.80 (3)
C(8)—C(9)—H(9)119.70 (4)C(2)—H(2A)—H(2B)35.43 (2)
C(10)—C(9)—H(9)120.45 (5)C(2)—H(2B)—H(2A)35.40 (2)
C(9)—C(10)—C(11)119.25 (4)C(13)—H(13A)—H(13B)37.21 (2)
C(9)—C(10)—H(10)120.78 (4)C(13)—H(13B)—H(13A)37.28 (2)
C(11)—C(10)—H(10)119.96 (4)C(14)—H(14A)—H(14B)36.59 (2)
C(6)—C(11)—C(10)120.44 (4)C(14)—H(14B)—H(14A)36.58 (2)
C(6)—C(11)—C(12)110.70 (3)C(15)—H(15A)—H(15B)35.08 (2)
C(10)—C(11)—C(12)128.70 (4)C(15)—H(15B)—H(15A)35.10 (2)
C(1)—C(12)—C(5)114.36 (3)C(18)—H(18A)—H(18B)37.07 (2)
C(1)—C(12)—C(11)116.54 (3)C(18)—H(18B)—H(18A)37.11 (2)
C(1)—C(12)—C(13)100.05 (3)C(20)—H(20A)—H(20B)36.55 (2)
C(5)—C(12)—C(11)102.56 (3)C(20)—H(20B)—H(20A)36.55 (2)
Selected geometric parameters (Å, º) for (III) top
O(18)—C(18)1.4324 (9)C(9)—H(9)1.0801 (7)
O(18)—C(19)1.4282 (8)C(10)—C(11)1.3890 (8)
O(21)—C(21)1.2305 (9)C(10)—H(10)1.0831 (7)
N(5)—C(5)1.4867 (7)C(11)—C(12)1.5039 (7)
N(5)—C(6)1.4147 (7)C(12)—C(13)1.5433 (6)
N(5)—C(21)1.3721 (7)C(13)—C(14)1.5259 (8)
N(14)—C(1)1.4936 (8)C(13)—H(13A)1.0735 (5)
N(14)—C(14)1.4752 (8)C(13)—H(13B)1.0723 (5)
N(14)—C(15)1.4689 (8)C(14)—H(14A)1.0723 (5)
C(1)—C(2)1.5210 (7)C(14)—H(14B)1.0735 (6)
C(1)—C(12)1.5459 (6)C(15)—C(16)1.5057 (8)
C(1)—H(1)1.0704 (5)C(15)—H(15A)1.0743 (7)
C(2)—C(3)1.5344 (7)C(15)—H(15B)1.0732 (7)
C(2)—H(2A)1.0721 (5)C(16)—C(17)1.3404 (8)
C(2)—H(2B)1.0741 (6)C(17)—C(18)1.5060 (9)
C(3)—C(4)1.5369 (7)C(17)—H(17)1.0674 (7)
C(3)—C(16)1.5218 (8)C(18)—H(18A)1.0739 (7)
C(3)—H(3)1.0693 (4)C(18)—H(18B)1.0726 (6)
C(4)—C(5)1.5344 (6)C(19)—C(20)1.5458 (8)
C(4)—C(19)1.5358 (6)C(19)—H(19)1.0691 (5)
C(4)—H(4)1.0702 (5)C(20)—C(21)1.5163 (8)
C(5)—C(12)1.5569 (6)C(20)—H(20A)1.0726 (5)
C(5)—H(5)1.0714 (5)C(20)—H(20B)1.0724 (6)
C(6)—C(7)1.3966 (8)H(2A)—H(2B)1.7478
C(6)—C(11)1.4003 (7)H(13A)—H(13B)1.6953
C(7)—C(8)1.4024 (11)H(14A)—H(14B)1.7203
C(7)—H(7)1.0854 (8)H(15A)—H(15B)1.7630
C(8)—C(9)1.3961 (13)H(18A)—H(18B)1.6913
C(8)—H(8)1.0818 (7)H(20A)—H(20B)1.6952
C(9)—C(10)1.3980 (10)
C(18)—O(18)—C(19)114.46 (5)C(5)—C(12)—C(13)111.37 (4)
C(5)—N(5)—C(6)109.68 (4)C(11)—C(12)—C(13)112.32 (4)
C(5)—N(5)—C(21)118.73 (5)C(12)—C(13)—C(14)102.31 (4)
C(6)—N(5)—C(21)124.46 (5)C(12)—C(13)—H(13A)109.38 (4)
C(1)—N(14)—C(14)108.53 (5)C(12)—C(13)—H(13B)112.53 (4)
C(1)—N(14)—C(15)113.60 (5)C(14)—C(13)—H(13A)112.38 (5)
C(14)—N(14)—C(15)113.29 (5)C(14)—C(13)—H(13B)115.95 (5)
N(14)—C(1)—C(2)111.63 (5)H(13A)—C(13)—H(13B)104.38 (4)
N(14)—C(1)—C(12)105.52 (4)N(14)—C(14)—C(13)104.19 (5)
N(14)—C(1)—H(1)110.05 (4)N(14)—C(14)—H(14A)112.72 (5)
C(2)—C(1)—C(12)114.18 (4)N(14)—C(14)—H(14B)107.47 (5)
C(2)—C(1)—H(1)109.23 (4)C(13)—C(14)—H(14A)113.34 (5)
C(12)—C(1)—H(1)106.02 (4)C(13)—C(14)—H(14B)112.50 (5)
C(1)—C(2)—C(3)108.68 (4)H(14A)—C(14)—H(14B)106.59 (5)
C(1)—C(2)—H(2A)110.66 (5)N(14)—C(15)—C(16)111.18 (5)
C(1)—C(2)—H(2B)107.87 (5)N(14)—C(15)—H(15A)106.32 (5)
C(3)—C(2)—H(2A)109.54 (5)N(14)—C(15)—H(15B)108.25 (6)
C(3)—C(2)—H(2B)111.03 (5)C(16)—C(15)—H(15A)110.66 (6)
H(2A)—C(2)—H(2B)109.05 (4)C(16)—C(15)—H(15B)109.99 (5)
C(2)—C(3)—C(4)106.34 (4)H(15A)—C(15)—H(15B)110.36 (5)
C(2)—C(3)—C(16)108.83 (4)C(3)—C(16)—C(15)114.77 (5)
C(2)—C(3)—H(3)108.85 (4)C(3)—C(16)—C(17)122.25 (5)
C(4)—C(3)—C(16)114.78 (4)C(15)—C(16)—C(17)122.90 (6)
C(4)—C(3)—H(3)109.59 (4)C(16)—C(17)—C(18)121.84 (6)
C(16)—C(3)—H(3)108.31 (4)C(16)—C(17)—H(17)118.68 (6)
C(3)—C(4)—C(5)113.28 (4)C(18)—C(17)—H(17)119.47 (6)
C(3)—C(4)—C(19)118.46 (4)O(18)—C(18)—C(17)111.37 (5)
C(3)—C(4)—H(4)105.27 (4)O(18)—C(18)—H(18A)110.26 (6)
C(5)—C(4)—C(19)107.82 (4)O(18)—C(18)—H(18B)106.91 (6)
C(5)—C(4)—H(4)103.69 (4)C(17)—C(18)—H(18A)112.89 (6)
C(19)—C(4)—H(4)107.08 (4)C(17)—C(18)—H(18B)111.02 (6)
N(5)—C(5)—C(4)106.22 (4)H(18A)—C(18)—H(18B)103.99 (5)
N(5)—C(5)—C(12)104.67 (4)O(18)—C(19)—C(4)114.65 (5)
N(5)—C(5)—H(5)109.33 (4)O(18)—C(19)—C(20)104.95 (5)
C(4)—C(5)—C(12)116.94 (4)O(18)—C(19)—H(19)107.25 (5)
C(4)—C(5)—H(5)110.18 (4)C(4)—C(19)—C(20)109.72 (4)
C(12)—C(5)—H(5)109.14 (4)C(4)—C(19)—H(19)108.45 (4)
N(5)—C(6)—C(7)129.34 (6)C(20)—C(19)—H(19)111.82 (4)
N(5)—C(6)—C(11)109.50 (5)C(19)—C(20)—C(21)116.56 (4)
C(7)—C(6)—C(11)121.16 (6)C(19)—C(20)—H(20A)110.67 (5)
C(6)—C(7)—C(8)117.62 (7)C(19)—C(20)—H(20B)105.37 (5)
C(6)—C(7)—H(7)120.76 (7)C(21)—C(20)—H(20A)109.78 (5)
C(8)—C(7)—H(7)121.60 (6)C(21)—C(20)—H(20B)109.24 (5)
C(7)—C(8)—C(9)121.61 (6)H(20A)—C(20)—H(20B)104.44 (5)
C(7)—C(8)—H(8)117.24 (9)O(21)—C(21)—N(5)122.44 (7)
C(9)—C(8)—H(8)121.15 (8)O(21)—C(21)—C(20)122.71 (6)
C(8)—C(9)—C(10)119.85 (7)N(5)—C(21)—C(20)114.84 (5)
C(8)—C(9)—H(9)120.44 (8)C(2)—H(2A)—H(2B)35.51 (3)
C(10)—C(9)—H(9)119.71 (9)C(2)—H(2B)—H(2A)35.44 (3)
C(9)—C(10)—C(11)119.27 (7)C(13)—H(13A)—H(13B)37.79 (3)
C(9)—C(10)—H(10)120.38 (6)C(13)—H(13B)—H(13A)37.83 (3)
C(11)—C(10)—H(10)120.35 (6)C(14)—H(14A)—H(14B)36.73 (3)
C(6)—C(11)—C(10)120.45 (5)C(14)—H(14B)—H(14A)36.68 (3)
C(6)—C(11)—C(12)110.73 (4)C(15)—H(15A)—H(15B)34.80 (3)
C(10)—C(11)—C(12)128.66 (5)C(15)—H(15B)—H(15A)34.84 (3)
C(1)—C(12)—C(5)114.30 (4)C(18)—H(18A)—H(18B)37.98 (3)
C(1)—C(12)—C(11)116.60 (4)C(18)—H(18B)—H(18A)38.03 (3)
C(1)—C(12)—C(13)100.09 (4)C(20)—H(20A)—H(20B)37.78 (3)
C(5)—C(12)—C(11)102.55 (4)C(20)—H(20B)—H(20A)37.79 (3)
Selected geometric parameters (Å, º) for (IV) top
O(18)—C(18)1.4335 (5)C(9)—H(9)1.0840 (4)
O(18)—C(19)1.4297 (5)C(10)—C(11)1.3936 (5)
O(21)—C(21)1.2284 (5)C(10)—H(10)1.0836 (4)
N(5)—C(5)1.4872 (4)C(11)—C(12)1.5042 (4)
N(5)—C(6)1.4178 (5)C(12)—C(13)1.5475 (5)
N(5)—C(21)1.3761 (5)C(13)—C(14)1.5254 (5)
N(14)—C(1)1.4924 (5)C(13)—H(13A)1.0738 (4)
N(14)—C(14)1.4808 (5)C(13)—H(13B)1.0728 (3)
N(14)—C(15)1.4705 (5)C(14)—H(14A)1.0729 (4)
C(1)—C(2)1.5255 (5)C(14)—H(14B)1.0732 (4)
C(1)—C(12)1.5509 (4)C(15)—C(16)1.5133 (5)
C(1)—H(1)1.0703 (3)C(15)—H(15A)1.0731 (4)
C(2)—C(3)1.5393 (5)C(15)—H(15B)1.0733 (4)
C(2)—H(2A)1.0724 (3)C(16)—C(17)1.3436 (5)
C(2)—H(2B)1.0731 (3)C(17)—C(18)1.5111 (5)
C(3)—C(4)1.5392 (4)C(17)—H(17)1.0700 (4)
C(3)—C(16)1.5240 (5)C(18)—H(18A)1.0730 (4)
C(3)—H(3)1.0696 (3)C(18)—H(18B)1.0729 (4)
C(4)—C(5)1.5403 (5)C(19)—C(20)1.5478 (5)
C(4)—C(19)1.5414 (5)C(19)—H(19)1.0705 (4)
C(4)—H(4)1.0704 (3)C(20)—C(21)1.5167 (5)
C(5)—C(12)1.5623 (4)C(20)—H(20A)1.0729 (4)
C(5)—H(5)1.0701 (3)C(20)—H(20B)1.0732 (4)
C(6)—C(7)1.3965 (4)H(2A)—H(2B)1.7283
C(6)—C(11)1.4014 (5)H(13A)—H(13B)1.7022
C(7)—C(8)1.4055 (6)H(14A)—H(14B)1.7457
C(7)—H(7)1.0845 (4)H(15A)—H(15B)1.7446
C(8)—C(9)1.4014 (6)H(18A)—H(18B)1.7171
C(8)—H(8)1.0832 (4)H(20A)—H(20B)1.7302
C(9)—C(10)1.3994 (5)
C(18)—O(18)—C(19)114.32 (3)C(5)—C(12)—C(13)111.38 (3)
C(5)—N(5)—C(6)109.53 (3)C(11)—C(12)—C(13)112.34 (3)
C(5)—N(5)—C(21)118.56 (3)C(12)—C(13)—C(14)102.13 (3)
C(6)—N(5)—C(21)124.85 (3)C(12)—C(13)—H(13A)109.51 (3)
C(1)—N(14)—C(14)108.66 (3)C(12)—C(13)—H(13B)112.97 (3)
C(1)—N(14)—C(15)113.56 (3)C(14)—C(13)—H(13A)111.76 (3)
C(14)—N(14)—C(15)113.24 (3)C(14)—C(13)—H(13B)115.63 (3)
N(14)—C(1)—C(2)111.75 (3)H(13A)—C(13)—H(13B)104.93 (3)
N(14)—C(1)—C(12)105.33 (3)N(14)—C(14)—C(13)104.15 (3)
N(14)—C(1)—H(1)108.72 (3)N(14)—C(14)—H(14A)111.52 (3)
C(2)—C(1)—C(12)114.19 (3)N(14)—C(14)—H(14B)108.91 (3)
C(2)—C(1)—H(1)108.99 (3)C(13)—C(14)—H(14A)112.78 (3)
C(12)—C(1)—H(1)107.64 (3)C(13)—C(14)—H(14B)110.52 (3)
C(1)—C(2)—C(3)108.60 (3)H(14A)—C(14)—H(14B)108.87 (3)
C(1)—C(2)—H(2A)111.93 (3)N(14)—C(15)—C(16)111.19 (3)
C(1)—C(2)—H(2B)107.78 (3)N(14)—C(15)—H(15A)108.42 (3)
C(3)—C(2)—H(2A)109.84 (3)N(14)—C(15)—H(15B)108.73 (3)
C(3)—C(2)—H(2B)111.36 (3)C(16)—C(15)—H(15A)109.25 (3)
H(2A)—C(2)—H(2B)107.33 (3)C(16)—C(15)—H(15B)110.45 (3)
C(2)—C(3)—C(4)106.61 (3)H(15A)—C(15)—H(15B)108.75 (3)
C(2)—C(3)—C(16)108.83 (3)C(3)—C(16)—C(15)114.61 (3)
C(2)—C(3)—H(3)108.71 (3)C(3)—C(16)—C(17)122.16 (3)
C(4)—C(3)—C(16)114.58 (3)C(15)—C(16)—C(17)123.14 (3)
C(4)—C(3)—H(3)108.95 (3)C(16)—C(17)—C(18)122.05 (3)
C(16)—C(3)—H(3)109.02 (3)C(16)—C(17)—H(17)117.89 (3)
C(3)—C(4)—C(5)113.29 (3)C(18)—C(17)—H(17)120.05 (3)
C(3)—C(4)—C(19)118.74 (3)O(18)—C(18)—C(17)111.15 (3)
C(3)—C(4)—H(4)103.82 (3)O(18)—C(18)—H(18A)109.84 (3)
C(5)—C(4)—C(19)107.70 (3)O(18)—C(18)—H(18B)106.05 (3)
C(5)—C(4)—H(4)104.64 (3)C(17)—C(18)—H(18A)112.36 (3)
C(19)—C(4)—H(4)107.52 (3)C(17)—C(18)—H(18B)110.86 (3)
N(5)—C(5)—C(4)106.21 (3)H(18A)—C(18)—H(18B)106.29 (3)
N(5)—C(5)—C(12)104.70 (2)O(18)—C(19)—C(4)114.61 (3)
N(5)—C(5)—H(5)107.98 (3)O(18)—C(19)—C(20)104.84 (3)
C(4)—C(5)—C(12)116.89 (3)O(18)—C(19)—H(19)107.07 (3)
C(4)—C(5)—H(5)111.13 (3)C(4)—C(19)—C(20)109.82 (3)
C(12)—C(5)—H(5)109.35 (3)C(4)—C(19)—H(19)107.93 (3)
N(5)—C(6)—C(7)129.01 (3)C(20)—C(19)—H(19)112.64 (3)
N(5)—C(6)—C(11)109.70 (3)C(19)—C(20)—C(21)116.36 (3)
C(7)—C(6)—C(11)121.29 (3)C(19)—C(20)—H(20A)109.07 (3)
C(6)—C(7)—C(8)117.52 (3)C(19)—C(20)—H(20B)106.06 (3)
C(6)—C(7)—H(7)122.47 (4)C(21)—C(20)—H(20A)111.09 (3)
C(8)—C(7)—H(7)120.01 (3)C(21)—C(20)—H(20B)106.32 (3)
C(7)—C(8)—C(9)121.66 (3)H(20A)—C(20)—H(20B)107.45 (3)
C(7)—C(8)—H(8)118.10 (4)O(21)—C(21)—N(5)122.48 (4)
C(9)—C(8)—H(8)120.24 (4)O(21)—C(21)—C(20)122.46 (3)
C(8)—C(9)—C(10)119.83 (3)N(5)—C(21)—C(20)115.04 (3)
C(8)—C(9)—H(9)120.75 (3)C(2)—H(2A)—H(2B)36.351 (18)
C(10)—C(9)—H(9)119.42 (4)C(2)—H(2B)—H(2A)36.322 (17)
C(9)—C(10)—C(11)119.10 (3)C(13)—H(13A)—H(13B)37.514 (18)
C(9)—C(10)—H(10)120.42 (3)C(13)—H(13B)—H(13A)37.554 (19)
C(11)—C(10)—H(10)120.46 (3)C(14)—H(14A)—H(14B)35.572 (19)
C(6)—C(11)—C(10)120.56 (3)C(14)—H(14B)—H(14A)35.563 (19)
C(6)—C(11)—C(12)110.65 (3)C(15)—H(15A)—H(15B)35.632 (19)
C(10)—C(11)—C(12)128.61 (3)C(15)—H(15B)—H(15A)35.622 (18)
C(1)—C(12)—C(5)114.38 (3)C(18)—H(18A)—H(18B)36.853 (19)
C(1)—C(12)—C(11)116.43 (3)C(18)—H(18B)—H(18A)36.86 (2)
C(1)—C(12)—C(13)100.15 (2)C(20)—H(20A)—H(20B)36.283 (19)
C(5)—C(12)—C(11)102.56 (2)C(20)—H(20B)—H(20A)36.270 (19)
 

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