research papers
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104032781/lc5019sup1.cif | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768104032781/lc5019sup2.pdf |
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).
(I) Strychnine top
Crystal data top
C21H22N2O2 | F(000) = 712 |
Mr = 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 |
Refinement top
Refinement on F | 922 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.017 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.018 | (Δ/σ)max = 0.199 |
S = 0.47 | Δρmax = 0.16 e Å−3 |
8480 reflections | Δρmin = −0.12 e Å−3 |
Crystal data top
C21H22N2O2 | V = 1599.65 Å3 |
Mr = 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 |
Refinement top
R[F2 > 2σ(F2)] = 0.017 | 0 restraints |
wR(F2) = 0.018 | (Δ/σ)max = 0.199 |
S = 0.47 | Δρmax = 0.16 e Å−3 |
8480 reflections | Δρmin = −0.12 e Å−3 |
922 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/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) | 0.54862 | 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 |
Mr = 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 |
Refinement top
Refinement on F | 922 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.017 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.018 | (Δ/σ)max = 0.003 |
S = 0.93 | Δρmax = 0.19 e Å−3 |
9430 reflections | Δρmin = −0.11 e Å−3 |
Crystal data top
C21H22N2O2 | V = 1598.23 Å3 |
Mr = 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 |
Refinement top
R[F2 > 2σ(F2)] = 0.017 | 922 parameters |
wR(F2) = 0.018 | 0 restraints |
S = 0.93 | Δρmax = 0.19 e Å−3 |
9430 reflections | Δρmin = −0.11 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/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) | 0.54751 | 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 |
Mr = 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 |
Refinement top
Refinement on F | 922 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.023 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.016 | (Δ/σ)max = 0.007 |
S = 0.69 | Δρmax = 0.16 e Å−3 |
8192 reflections | Δρmin = −0.14 e Å−3 |
Crystal data top
C21H22N2O2 | V = 1599.65 Å3 |
Mr = 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 |
Refinement top
R[F2 > 2σ(F2)] = 0.023 | 922 parameters |
wR(F2) = 0.016 | 0 restraints |
S = 0.69 | Δρmax = 0.16 e Å−3 |
8192 reflections | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/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) | 0.54812 | 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 |
Mr = 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 |
Refinement top
Refinement on F | 922 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.02 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.021 | (Δ/σ)max = 0.069 |
S = 1.21 | Δρmax = 0.28 e Å−3 |
9466 reflections | Δρmin = −0.20 e Å−3 |
Crystal data top
C21H22N2O2 | V = 1598.23 Å3 |
Mr = 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 |
Refinement top
R[F2 > 2σ(F2)] = 0.02 | 922 parameters |
wR(F2) = 0.021 | 0 restraints |
S = 1.21 | Δρmax = 0.28 e Å−3 |
9466 reflections | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/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) | 0.54496 | 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 |
Mr | 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 | ?, ?, ? | ?, ?, ? | ?, ?, ? | ?, ?, ? |
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 reflections | 8480 | 9430 | 8192 | 9466 |
No. of parameters | 922 | 922 | 922 | 922 |
(Δ/σ)max | 0.199 | 0.003 | 0.007 | 0.069 |
Δρmax, Δρmin (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) |