Charge density of (−)-strychnine from 100 to 15 K, a comparison of four data sets

Messerschmidt, M.; Scheins, S.; Luger, P.

doi:10.1107/S0108768104032781

Charge density of (−)-strychnine from 100 to 15 K, a comparison of four data sets

M. Messerschmidt, S. Scheins and P. Luger

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.

Keywords: charge density; strychnine; oligocyclic.

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Supporting information

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

(I) Strychnine top

Crystal data top

C₂₁H₂₂N₂O₂	F(000) = 712
M_r = 334.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9605 reflections
Hall symbol: P 2ac 2ab	θ = 2.4–48.1°
a = 11.309 (1) Å	µ = 0.09 mm⁻¹
b = 11.785 (1) Å	T = 100 K
c = 12.002 (1) Å	, colorless
V = 1599.65 Å³	× × mm
Z = 4

Data collection top

Graphit monochromator	k = ?→?
h = ?→?	l = ?→?

Refinement top

Refinement on F	922 parameters
Least-squares matrix: full	0 restraints
R[F² > 2σ(F²)] = 0.017	w1 = 1/[s²(F_o)]
wR(F²) = 0.018	(Δ/σ)_max = 0.199
S = 0.47	Δρ_max = 0.16 e Å⁻³
8480 reflections	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₂	V = 1599.65 Å³
M_r = 334.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.309 (1) Å	µ = 0.09 mm⁻¹
b = 11.785 (1) Å	T = 100 K
c = 12.002 (1) Å	× × mm

Data collection top

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.018	(Δ/σ)_max = 0.199
S = 0.47	Δρ_max = 0.16 e Å⁻³
8480 reflections	Δρ_min = −0.12 e Å⁻³
922 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)	0.54862	0.39613	0.72553	0.022 (4)
H(2A)	0.4617	0.42273	0.91132	0.051 (5)
H(2B)	0.60866	0.37557	0.91406	0.027 (4)
H(3)	0.46801	0.26901	1.04619	0.032 (4)
H(4)	0.6561	0.20206	0.9717	0.028 (3)
H(5)	0.54335	0.0584	0.7992	0.023 (3)
H(7)	0.97233	0.09179	0.77366	0.036 (4)
H(8)	1.06247	0.25128	0.67488	0.040 (5)
H(9)	0.93932	0.41049	0.60056	0.056 (6)
H(10)	0.71932	0.40497	0.62621	0.037 (5)
H(13A)	0.55396	0.24245	0.56322	0.022 (4)
H(13B)	0.56403	0.10382	0.60116	0.018 (4)
H(14A)	0.34377	0.1958	0.59342	0.028 (4)
H(14B)	0.37919	0.11904	0.71367	0.021 (4)
H(15A)	0.23274	0.24308	0.78822	0.026 (4)
H(15B)	0.28533	0.3657	0.85251	0.050 (5)
H(17)	0.21911	0.09684	0.92158	0.044 (5)
H(18A)	0.38027	0.08643	1.11827	0.029 (5)
H(18B)	0.2988	−0.02292	1.06994	0.025 (4)
H(19)	0.57535	0.06753	1.10174	0.022 (3)
H(20A)	0.70906	−0.07251	1.04949	0.025 (5)
H(20B)	0.62408	−0.09913	0.93106	0.033 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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

C₂₁H₂₂N₂O₂	F(000) = 712
M_r = 334.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 8611 reflections
Hall symbol: P 2ac 2ab	θ = 2.4–37.7°
a = 11.326 (1) Å	µ = 0.09 mm⁻¹
b = 11.765 (1) Å	T = 25 K
c = 11.994 (1) Å	, colorless
V = 1598.23 Å³	× × mm
Z = 4

Data collection top

Radiation source: sealed X-ray tube	k = ?→?
Graphit monochromator	l = ?→?
h = ?→?

Refinement top

Refinement on F	922 parameters
Least-squares matrix: full	0 restraints
R[F² > 2σ(F²)] = 0.017	w1 = 1/[s²(F_o)]
wR(F²) = 0.018	(Δ/σ)_max = 0.003
S = 0.93	Δρ_max = 0.19 e Å⁻³
9430 reflections	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₂	V = 1598.23 Å³
M_r = 334.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.326 (1) Å	µ = 0.09 mm⁻¹
b = 11.765 (1) Å	T = 25 K
c = 11.994 (1) Å	× × mm

Data collection top

Refinement top

R[F² > 2σ(F²)] = 0.017	922 parameters
wR(F²) = 0.018	0 restraints
S = 0.93	Δρ_max = 0.19 e Å⁻³
9430 reflections	Δρ_min = −0.11 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)	0.54751	0.39733	0.72578	0.011 (3)
H(2A)	0.46011	0.42155	0.9133	0.029 (4)
H(2B)	0.60781	0.37822	0.91497	0.027 (4)
H(3)	0.47307	0.26923	1.0471	0.022 (3)
H(4)	0.65631	0.20145	0.97313	0.026 (3)
H(5)	0.54418	0.05783	0.79953	0.021 (3)
H(7)	0.97671	0.09609	0.77505	0.016 (3)
H(8)	1.06224	0.25338	0.67359	0.029 (4)
H(9)	0.93831	0.4119	0.59979	0.032 (5)
H(10)	0.71905	0.40614	0.62646	0.033 (5)
H(13A)	0.55294	0.24411	0.56378	0.022 (4)
H(13B)	0.56427	0.10422	0.60051	0.017 (4)
H(14A)	0.34293	0.19328	0.59387	0.025 (4)
H(14B)	0.37853	0.11837	0.71276	0.014 (3)
H(15A)	0.23177	0.24494	0.78906	0.031 (4)
H(15B)	0.2893	0.36629	0.85479	0.027 (4)
H(17)	0.21904	0.09524	0.92405	0.033 (4)
H(18A)	0.38115	0.08633	1.11912	0.023 (4)
H(18B)	0.2988	−0.02389	1.06773	0.016 (4)
H(19)	0.57498	0.067	1.10231	0.014 (3)
H(20A)	0.70794	−0.07555	1.04897	0.014 (4)
H(20B)	0.62369	−0.09942	0.93164	0.016 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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

C₂₁H₂₂N₂O₂	F(000) = 712
M_r = 334.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9605 reflections
Hall symbol: P 2ac 2ab	θ = 2.4–48.1°
a = 11.309 (1) Å	µ = 0.09 mm⁻¹
b = 11.785 (1) Å	T = 100 K
c = 12.002 (1) Å	, colorless
V = 1599.65 Å³	× × mm
Z = 4

Data collection top

Graphit monochromator	k = ?→?
h = ?→?	l = ?→?

Refinement top

Refinement on F	922 parameters
Least-squares matrix: full	0 restraints
R[F² > 2σ(F²)] = 0.023	w1 = 1/[s²(F_o)]
wR(F²) = 0.016	(Δ/σ)_max = 0.007
S = 0.69	Δρ_max = 0.16 e Å⁻³
8192 reflections	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₂	V = 1599.65 Å³
M_r = 334.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.309 (1) Å	µ = 0.09 mm⁻¹
b = 11.785 (1) Å	T = 100 K
c = 12.002 (1) Å	× × mm

Data collection top

Refinement top

R[F² > 2σ(F²)] = 0.023	922 parameters
wR(F²) = 0.016	0 restraints
S = 0.69	Δρ_max = 0.16 e Å⁻³
8192 reflections	Δρ_min = −0.14 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)	0.54812	0.39562	0.72458	0.026 (4)
H(2A)	0.4616	0.422	0.91274	0.038 (4)
H(2B)	0.60823	0.37525	0.91594	0.031 (4)
H(3)	0.47053	0.26967	1.04616	0.033 (4)
H(4)	0.65702	0.2004	0.97154	0.026 (4)
H(5)	0.5419	0.05929	0.7997	0.024 (4)
H(7)	0.97225	0.09249	0.77578	0.030 (4)
H(8)	1.06217	0.25219	0.67348	0.044 (6)
H(9)	0.93747	0.41124	0.6007	0.044 (6)
H(10)	0.71971	0.40452	0.62523	0.037 (5)
H(13A)	0.55427	0.24242	0.56338	0.030 (4)
H(13B)	0.56385	0.10396	0.60059	0.026 (4)
H(14A)	0.34402	0.19298	0.59298	0.034 (5)
H(14B)	0.37632	0.11961	0.71309	0.030 (4)
H(15A)	0.23186	0.24345	0.78936	0.037 (5)
H(15B)	0.28915	0.36558	0.85479	0.035 (5)
H(17)	0.21837	0.09656	0.92317	0.044 (6)
H(18A)	0.37945	0.08605	1.1185	0.036 (5)
H(18B)	0.29851	−0.02328	1.06835	0.027 (4)
H(19)	0.57571	0.06927	1.10121	0.024 (4)
H(20A)	0.70715	−0.07489	1.04924	0.025 (4)
H(20B)	0.62376	−0.10154	0.93483	0.026 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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

C₂₁H₂₂N₂O₂	F(000) = 712
M_r = 334.41	Mo Kα radiation, λ = 0.53 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 8611 reflections
Hall symbol: P 2ac 2ab	θ = 2.4–37.7°
a = 11.326 (1) Å	µ = 0.05 mm⁻¹
b = 11.765 (1) Å	T = 25 K
c = 11.994 (1) Å	, colorless
V = 1598.23 Å³	× × mm
Z = 4

Data collection top

Si double crystal monochromator	k = ?→?
h = ?→?	l = ?→?

Refinement top

Refinement on F	922 parameters
Least-squares matrix: full	0 restraints
R[F² > 2σ(F²)] = 0.02	w1 = 1/[s²(F_o)]
wR(F²) = 0.021	(Δ/σ)_max = 0.069
S = 1.21	Δρ_max = 0.28 e Å⁻³
9466 reflections	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₂	V = 1598.23 Å³
M_r = 334.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.326 (1) Å	µ = 0.05 mm⁻¹
b = 11.765 (1) Å	T = 25 K
c = 11.994 (1) Å	× × mm

Data collection top

Refinement top

R[F² > 2σ(F²)] = 0.02	922 parameters
wR(F²) = 0.021	0 restraints
S = 1.21	Δρ_max = 0.28 e Å⁻³
9466 reflections	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)	0.54496	0.39752	0.72468	0.023 (5)
H(2A)	0.46336	0.4238	0.91491	0.032 (5)
H(2B)	0.60815	0.37689	0.91582	0.020 (5)
H(3)	0.47233	0.27007	1.04701	0.015 (4)
H(4)	0.65616	0.20221	0.97294	0.024 (4)
H(5)	0.54424	0.05822	0.79907	0.012 (3)
H(7)	0.97491	0.09587	0.77662	0.026 (5)
H(8)	1.06206	0.25396	0.67125	0.022 (5)
H(9)	0.93665	0.41238	0.59865	0.014 (4)
H(10)	0.719	0.40505	0.62355	0.032 (5)
H(13A)	0.5525	0.24337	0.56317	0.021 (5)
H(13B)	0.56305	0.10419	0.59972	0.027 (5)
H(14A)	0.3443	0.19498	0.59296	0.014 (4)
H(14B)	0.37958	0.11786	0.7126	0.028 (5)
H(15A)	0.23052	0.24365	0.79305	0.036 (6)
H(15B)	0.28762	0.36592	0.85484	0.033 (5)
H(17)	0.21886	0.09685	0.92371	0.019 (4)
H(18A)	0.3819	0.08681	1.1189	0.019 (5)
H(18B)	0.29988	−0.02459	1.06863	0.018 (5)
H(19)	0.57593	0.06969	1.10184	0.022 (4)
H(20A)	0.70592	−0.0748	1.05056	0.034 (6)
H(20B)	0.62577	−0.0996	0.93021	0.020 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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 formula	C₂₁H₂₂N₂O₂	C₂₁H₂₂N₂O₂	C₂₁H₂₂N₂O₂	C₂₁H₂₂N₂O₂
M_r	334.41	334.41	334.41	334.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁
Temperature (K)	100	25	100	25
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)
V (Å³)	1599.65	1598.23	1599.65	1598.23
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.09	0.09	0.05
Crystal size (mm)	× ×	× ×	× ×	× ×

Data collection
Diffractometer	?	?	?	?
Absorption correction	–	–	–	–
No. of measured, independent and observed (?) reflections	?, ?, ?	?, ?, ?	?, ?, ?	?, ?, ?
R_int	?	?	?	?

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 reflections	8480	9430	8192	9466
No. of parameters	922	922	922	922
(Δ/σ)_max	0.199	0.003	0.007	0.069
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.12	0.19, −0.11	0.16, −0.14	0.28, −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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