


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810036664/jj2056sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810036664/jj2056Isup2.hkl |
CCDC reference: 797785
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean
(C-C) = 0.010 Å
- Disorder in solvent or counterion
- R factor = 0.059
- wR factor = 0.195
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C20B PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 31
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O4B PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 10 PLAT430_ALERT_2_C Short Inter D...A Contact O1A .. O1B .. 2.86 Ang. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 I0.06 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 5 I PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6 I PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
Alert level G PLAT432_ALERT_2_G Short Inter X...Y Contact I1B' .. C3A .. 3.44 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact O1A .. C1B .. 3.02 Ang. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12 PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 1.00 mm PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 40.00 Perc. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 PLAT808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! PLAT929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked !
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
The title compound was prepared by vacuum pyrolysis of berberine hydrochloride followed by alkylation with ethyl iodide (Iwasa et al., 1997). The crystals suitable for single-crystal X-ray diffraction were grown in DMSO-d6. The crystal was diffracted in the cold stream of an X-Stream 2000 Liquid nitrogen generator with an open-flow nitrogen cryostat with a nominal stability of 0.1 K.
The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints. The ethyl groups on the molecules were found to have some disorder, with the methylene carbon (C20B) demonstrating the largest thermal parameters. The disordered iodide anions were solved with two partially occupied positions. The anisotropic parameters Uxy were restrained for each of the iodide pairs during refinement.
Data collection: CrystalClear (Rigaku, 2009); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: CrystalStructure (Rigaku, 2009) and SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
2C21H20NO4+·2I−·H2O | Z = 2 |
Mr = 972.61 | F(000) = 972 |
Triclinic, P1 | Dx = 1.685 Mg m−3 |
Hall symbol: -P 1 | Melting point: 257 K |
a = 11.036 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.449 (4) Å | Cell parameters from 50086 reflections |
c = 14.086 (4) Å | θ = 3–27.5° |
α = 80.442 (6)° | µ = 1.70 mm−1 |
β = 71.121 (5)° | T = 93 K |
γ = 76.875 (5)° | Needle, yellow |
V = 1916.8 (9) Å3 | 1.00 × 0.10 × 0.10 mm |
Rigaku R-AXIS RAPID II image plate diffractometer | 8751 independent reflections |
Radiation source: Mo sealed tube | 4563 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.101 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.469, Tmax = 0.712 | l = −18→18 |
50086 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | All H-atom parameters refined |
S = 0.96 | Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 4.85 6.23 1.54 |
8751 reflections | (Δ/σ)max = 0.001 |
502 parameters | Δρmax = 1.75 e Å−3 |
12 restraints | Δρmin = −2.26 e Å−3 |
0 constraints |
2C21H20NO4+·2I−·H2O | γ = 76.875 (5)° |
Mr = 972.61 | V = 1916.8 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.036 (3) Å | Mo Kα radiation |
b = 13.449 (4) Å | µ = 1.70 mm−1 |
c = 14.086 (4) Å | T = 93 K |
α = 80.442 (6)° | 1.00 × 0.10 × 0.10 mm |
β = 71.121 (5)° |
Rigaku R-AXIS RAPID II image plate diffractometer | 8751 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4563 reflections with I > 2.0σ(I) |
Tmin = 0.469, Tmax = 0.712 | Rint = 0.101 |
50086 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 12 restraints |
wR(F2) = 0.195 | All H-atom parameters refined |
S = 0.96 | Δρmax = 1.75 e Å−3 |
8751 reflections | Δρmin = −2.26 e Å−3 |
502 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 0.7061 (5) | 0.4522 (4) | 0.7015 (4) | 0.0527 | |
C1A | 0.5927 (8) | 0.5331 (6) | 0.7096 (6) | 0.0517 | |
O2A | 0.5226 (6) | 0.5086 (4) | 0.6480 (4) | 0.0577 | |
C2A | 0.5222 (8) | 0.3441 (6) | 0.5954 (6) | 0.0554 | |
C3A | 0.5468 (8) | 0.1682 (6) | 0.5415 (6) | 0.0552 | |
C4A | 0.5678 (7) | 0.0617 (6) | 0.5900 (6) | 0.0511 | |
N1A | 0.7020 (5) | 0.0278 (4) | 0.5983 (4) | 0.0413 | |
C5A | 0.7560 (7) | −0.0722 (5) | 0.5920 (5) | 0.0413 | |
C6A | 0.9343 (6) | −0.2175 (5) | 0.6016 (5) | 0.0401 | |
C7A | 1.0547 (7) | −0.2531 (5) | 0.6186 (5) | 0.0436 | |
C8A | 1.1203 (6) | −0.1848 (5) | 0.6375 (5) | 0.0417 | |
C9A | 1.0685 (7) | −0.0817 (5) | 0.6410 (5) | 0.0440 | |
C10A | 0.8835 (6) | 0.0610 (5) | 0.6336 (5) | 0.0398 | |
C11A | 0.7418 (7) | 0.2722 (5) | 0.6670 (5) | 0.0462 | |
C12A | 0.6771 (7) | 0.3709 (5) | 0.6694 (5) | 0.0437 | |
C13A | 0.5686 (7) | 0.4057 (6) | 0.6358 (6) | 0.0490 | |
C14A | 0.5878 (7) | 0.2405 (5) | 0.5902 (5) | 0.0438 | |
C15A | 0.8781 (6) | −0.1118 (5) | 0.6061 (4) | 0.0392 | |
C16A | 0.9456 (6) | −0.0429 (5) | 0.6270 (5) | 0.0411 | |
C17A | 0.7628 (6) | 0.0966 (5) | 0.6204 (4) | 0.0378 | |
C18A | 0.6934 (6) | 0.2049 (5) | 0.6268 (5) | 0.0406 | |
O3A | 1.1012 (5) | −0.3557 (4) | 0.6163 (4) | 0.0471 | |
O4A | 0.8648 (5) | −0.2821 (3) | 0.5852 (3) | 0.0428 | |
C19A | 1.2226 (8) | −0.3942 (5) | 0.6361 (6) | 0.0497 | |
C20A | 0.9150 (8) | −0.3152 (6) | 0.4853 (5) | 0.0531 | |
C21A | 0.8288 (9) | −0.3797 (7) | 0.4743 (7) | 0.0662 | |
O1B | 0.7780 (5) | −0.4304 (3) | 0.8199 (4) | 0.0481 | |
C1B | 0.8993 (7) | −0.5023 (5) | 0.7914 (6) | 0.0507 | |
O2B | 0.9851 (5) | −0.4741 (4) | 0.8366 (4) | 0.0528 | |
C2B | 0.9914 (7) | −0.3031 (6) | 0.8764 (5) | 0.0471 | |
C3B | 0.9793 (7) | −0.1200 (5) | 0.9045 (5) | 0.0463 | |
C4B | 0.8775 (7) | −0.0374 (5) | 0.9633 (6) | 0.0468 | |
N1B | 0.7687 (5) | −0.0013 (4) | 0.9196 (4) | 0.0390 | |
C5B | 0.7139 (7) | 0.0966 (5) | 0.9225 (5) | 0.0442 | |
C6B | 0.5421 (7) | 0.2398 (5) | 0.8997 (5) | 0.0433 | |
C7B | 0.4229 (6) | 0.2745 (5) | 0.8790 (5) | 0.0423 | |
C8B | 0.3624 (6) | 0.2055 (5) | 0.8563 (5) | 0.0412 | |
C9B | 0.4177 (6) | 0.1029 (5) | 0.8509 (5) | 0.0399 | |
C10B | 0.6057 (6) | −0.0366 (5) | 0.8629 (4) | 0.0368 | |
C11B | 0.7373 (6) | −0.2504 (5) | 0.8535 (5) | 0.0415 | |
C12B | 0.8119 (6) | −0.3468 (5) | 0.8398 (5) | 0.0407 | |
C13B | 0.9343 (7) | −0.3723 (5) | 0.8522 (5) | 0.0449 | |
C14B | 0.9186 (6) | −0.2035 (5) | 0.8885 (5) | 0.0433 | |
C15B | 0.5975 (6) | 0.1356 (5) | 0.8969 (5) | 0.0399 | |
C16B | 0.5391 (6) | 0.0654 (5) | 0.8706 (4) | 0.0363 | |
C17B | 0.7212 (6) | −0.0725 (5) | 0.8861 (4) | 0.0371 | |
C18B | 0.7938 (6) | −0.1769 (5) | 0.8779 (5) | 0.0400 | |
O4B | 0.6121 (5) | 0.3048 (4) | 0.9131 (4) | 0.0498 | |
O3B | 0.3732 (5) | 0.3765 (4) | 0.8823 (4) | 0.0489 | |
C19B | 0.2472 (8) | 0.4115 (6) | 0.8666 (7) | 0.0569 | |
C20B | 0.5681 (9) | 0.3468 (11) | 1.0051 (8) | 0.0893 | |
C21B | 0.6740 (9) | 0.3896 (8) | 1.0199 (6) | 0.0634 | |
O5 | 1.2817 (6) | 0.0700 (5) | 0.6183 (4) | 0.0635 | |
I1A | 1.02838 (5) | 0.19860 (3) | 0.80552 (4) | 0.0447 | 0.9379 |
I1A' | 1.1037 (7) | 0.1783 (5) | 0.7437 (6) | 0.0447 | 0.0621 |
I1B | 1.39483 (6) | −0.16491 (4) | 0.75430 (5) | 0.0520 | 0.9057 |
I1B' | 1.4616 (6) | −0.1882 (4) | 0.7030 (5) | 0.0520 | 0.0943 |
H1A | 0.6187 | 0.5993 | 0.6853 | 0.0619* | |
H2A | 0.5380 | 0.5327 | 0.7790 | 0.0618* | |
H3A | 0.4499 | 0.3682 | 0.5718 | 0.0661* | |
H4A | 0.5966 | 0.1695 | 0.4707 | 0.0661* | |
H5A | 0.4542 | 0.1889 | 0.5483 | 0.0663* | |
H6A | 0.5042 | 0.0590 | 0.6571 | 0.0612* | |
H7A | 0.5560 | 0.0157 | 0.5490 | 0.0607* | |
H8A | 0.7107 | −0.1157 | 0.5775 | 0.0495* | |
H9A | 1.2018 | −0.2098 | 0.6474 | 0.0498* | |
H10A | 1.1145 | −0.0368 | 0.6524 | 0.0527* | |
H11A | 0.9261 | 0.1064 | 0.6479 | 0.0480* | |
H12A | 0.8143 | 0.2501 | 0.6909 | 0.0558* | |
H13A | 1.2430 | −0.4679 | 0.6357 | 0.0750* | |
H14A | 1.2168 | −0.3759 | 0.7007 | 0.0748* | |
H15A | 1.2896 | −0.3646 | 0.5852 | 0.0749* | |
H16A | 1.0021 | −0.3568 | 0.4784 | 0.0636* | |
H17A | 0.9200 | −0.2562 | 0.4342 | 0.0642* | |
H18A | 0.8548 | −0.3958 | 0.4057 | 0.0992* | |
H19A | 0.8354 | −0.4422 | 0.5184 | 0.0988* | |
H20A | 0.7397 | −0.3432 | 0.4928 | 0.0989* | |
H1B | 0.8849 | −0.5716 | 0.8167 | 0.0610* | |
H2B | 0.9354 | −0.4972 | 0.7183 | 0.0609* | |
H3B | 1.0747 | −0.3211 | 0.8837 | 0.0571* | |
H4B | 1.0408 | −0.1494 | 0.9427 | 0.0559* | |
H5B | 1.0244 | −0.0878 | 0.8384 | 0.0558* | |
H6B | 0.8441 | −0.0668 | 1.0323 | 0.0558* | |
H7B | 0.9172 | 0.0200 | 0.9622 | 0.0559* | |
H8B | 0.7535 | 0.1410 | 0.9415 | 0.0528* | |
H9B | 0.2816 | 0.2301 | 0.8448 | 0.0488* | |
H10B | 0.3754 | 0.0586 | 0.8342 | 0.0478* | |
H11B | 0.5706 | −0.0817 | 0.8411 | 0.0439* | |
H12B | 0.6540 | −0.2340 | 0.8465 | 0.0500* | |
H13B | 0.2236 | 0.4843 | 0.8700 | 0.0849* | |
H14B | 0.1834 | 0.3776 | 0.9178 | 0.0848* | |
H15B | 0.2506 | 0.3966 | 0.8011 | 0.0848* | |
H16B | 0.5428 | 0.2942 | 1.0590 | 0.1070* | |
H17B | 0.4937 | 0.4011 | 1.0052 | 0.1071* | |
H18B | 0.6422 | 0.4194 | 1.0829 | 0.0951* | |
H19B | 0.7468 | 0.3356 | 1.0206 | 0.0951* | |
H20B | 0.6997 | 0.4413 | 0.9653 | 0.0949* | |
H21 | 1.2190 | 0.0950 | 0.6740 | 0.0941* | |
H22 | 1.2916 | 0.0105 | 0.6502 | 0.0944* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.058 (3) | 0.040 (2) | 0.063 (3) | −0.006 (2) | −0.024 (2) | −0.005 (2) |
C1A | 0.055 (4) | 0.042 (3) | 0.061 (4) | −0.003 (3) | −0.022 (3) | −0.010 (3) |
O2A | 0.065 (3) | 0.045 (3) | 0.069 (3) | 0.000 (2) | −0.028 (3) | −0.019 (2) |
C2A | 0.059 (4) | 0.055 (4) | 0.062 (4) | −0.004 (3) | −0.033 (4) | −0.015 (3) |
C3A | 0.055 (4) | 0.059 (4) | 0.059 (4) | −0.011 (3) | −0.022 (3) | −0.013 (3) |
C4A | 0.044 (3) | 0.053 (4) | 0.065 (4) | −0.019 (3) | −0.024 (3) | −0.002 (3) |
N1A | 0.045 (3) | 0.043 (3) | 0.041 (3) | −0.013 (2) | −0.016 (2) | −0.006 (2) |
C5A | 0.048 (3) | 0.045 (3) | 0.038 (3) | −0.018 (3) | −0.017 (3) | −0.004 (2) |
C6A | 0.048 (3) | 0.038 (3) | 0.040 (3) | −0.011 (3) | −0.015 (3) | −0.009 (2) |
C7A | 0.052 (4) | 0.042 (3) | 0.041 (3) | −0.012 (3) | −0.017 (3) | −0.005 (2) |
C8A | 0.043 (3) | 0.046 (3) | 0.041 (3) | −0.010 (3) | −0.018 (3) | −0.003 (3) |
C9A | 0.052 (4) | 0.048 (3) | 0.041 (3) | −0.018 (3) | −0.018 (3) | −0.009 (3) |
C10A | 0.041 (3) | 0.044 (3) | 0.041 (3) | −0.006 (3) | −0.020 (3) | −0.010 (2) |
C11A | 0.055 (4) | 0.041 (3) | 0.050 (4) | −0.017 (3) | −0.022 (3) | −0.001 (3) |
C12A | 0.051 (4) | 0.045 (3) | 0.038 (3) | −0.016 (3) | −0.014 (3) | −0.004 (2) |
C13A | 0.052 (4) | 0.048 (4) | 0.050 (4) | −0.004 (3) | −0.018 (3) | −0.013 (3) |
C14A | 0.044 (3) | 0.043 (3) | 0.048 (3) | −0.006 (3) | −0.016 (3) | −0.011 (3) |
C15A | 0.048 (3) | 0.042 (3) | 0.032 (3) | −0.013 (3) | −0.013 (2) | −0.006 (2) |
C16A | 0.047 (3) | 0.046 (3) | 0.033 (3) | −0.015 (3) | −0.013 (3) | −0.003 (2) |
C17A | 0.041 (3) | 0.042 (3) | 0.035 (3) | −0.009 (2) | −0.014 (2) | −0.007 (2) |
C18A | 0.042 (3) | 0.046 (3) | 0.037 (3) | −0.010 (3) | −0.015 (3) | −0.006 (2) |
O3A | 0.053 (3) | 0.040 (2) | 0.055 (3) | −0.007 (2) | −0.024 (2) | −0.008 (2) |
O4A | 0.051 (3) | 0.041 (2) | 0.044 (2) | −0.016 (2) | −0.017 (2) | −0.0088 (18) |
C19A | 0.058 (4) | 0.038 (3) | 0.058 (4) | −0.002 (3) | −0.027 (3) | −0.008 (3) |
C20A | 0.054 (4) | 0.068 (5) | 0.046 (4) | −0.016 (3) | −0.016 (3) | −0.019 (3) |
C21A | 0.067 (5) | 0.075 (5) | 0.066 (5) | −0.034 (4) | −0.009 (4) | −0.027 (4) |
O1B | 0.046 (2) | 0.033 (2) | 0.071 (3) | −0.0049 (19) | −0.026 (2) | −0.011 (2) |
C1B | 0.046 (4) | 0.038 (3) | 0.068 (4) | 0.000 (3) | −0.021 (3) | −0.011 (3) |
O2B | 0.056 (3) | 0.039 (2) | 0.070 (3) | 0.001 (2) | −0.026 (3) | −0.020 (2) |
C2B | 0.045 (3) | 0.054 (4) | 0.046 (3) | −0.002 (3) | −0.017 (3) | −0.017 (3) |
C3B | 0.042 (3) | 0.050 (4) | 0.053 (4) | −0.006 (3) | −0.019 (3) | −0.015 (3) |
C4B | 0.050 (4) | 0.043 (3) | 0.058 (4) | −0.004 (3) | −0.030 (3) | −0.013 (3) |
N1B | 0.035 (2) | 0.044 (3) | 0.047 (3) | −0.010 (2) | −0.021 (2) | −0.007 (2) |
C5B | 0.049 (4) | 0.041 (3) | 0.050 (3) | −0.014 (3) | −0.020 (3) | −0.007 (3) |
C6B | 0.047 (3) | 0.039 (3) | 0.048 (3) | −0.011 (3) | −0.017 (3) | −0.008 (3) |
C7B | 0.042 (3) | 0.041 (3) | 0.044 (3) | −0.006 (3) | −0.012 (3) | −0.010 (3) |
C8B | 0.042 (3) | 0.042 (3) | 0.043 (3) | −0.005 (3) | −0.017 (3) | −0.008 (2) |
C9B | 0.042 (3) | 0.044 (3) | 0.042 (3) | −0.012 (3) | −0.020 (3) | −0.008 (2) |
C10B | 0.040 (3) | 0.039 (3) | 0.039 (3) | −0.010 (2) | −0.018 (2) | −0.008 (2) |
C11B | 0.044 (3) | 0.034 (3) | 0.050 (3) | −0.008 (2) | −0.019 (3) | −0.003 (2) |
C12B | 0.042 (3) | 0.035 (3) | 0.049 (3) | −0.012 (2) | −0.015 (3) | −0.005 (2) |
C13B | 0.049 (4) | 0.042 (3) | 0.047 (3) | −0.002 (3) | −0.020 (3) | −0.009 (3) |
C14B | 0.042 (3) | 0.051 (4) | 0.044 (3) | −0.011 (3) | −0.017 (3) | −0.012 (3) |
C15B | 0.044 (3) | 0.041 (3) | 0.040 (3) | −0.012 (3) | −0.016 (3) | −0.007 (2) |
C16B | 0.033 (3) | 0.042 (3) | 0.037 (3) | −0.009 (2) | −0.010 (2) | −0.009 (2) |
C17B | 0.039 (3) | 0.042 (3) | 0.037 (3) | −0.011 (2) | −0.016 (2) | −0.008 (2) |
C18B | 0.043 (3) | 0.041 (3) | 0.041 (3) | −0.010 (3) | −0.017 (3) | −0.006 (2) |
O4B | 0.054 (3) | 0.045 (2) | 0.055 (3) | −0.017 (2) | −0.012 (2) | −0.017 (2) |
O3B | 0.053 (3) | 0.036 (2) | 0.062 (3) | −0.004 (2) | −0.024 (2) | −0.008 (2) |
C19B | 0.062 (5) | 0.045 (4) | 0.071 (5) | 0.001 (3) | −0.035 (4) | −0.010 (3) |
C20B | 0.062 (5) | 0.154 (11) | 0.070 (6) | −0.041 (6) | −0.002 (4) | −0.068 (7) |
C21B | 0.062 (5) | 0.092 (6) | 0.049 (4) | −0.036 (5) | −0.019 (4) | −0.010 (4) |
O5 | 0.060 (3) | 0.081 (4) | 0.054 (3) | −0.023 (3) | −0.017 (3) | −0.006 (3) |
I1A | 0.0507 (3) | 0.0426 (2) | 0.0484 (3) | −0.01080 (19) | −0.0248 (2) | −0.00267 (18) |
I1A' | 0.0507 (3) | 0.0426 (2) | 0.0484 (3) | −0.01080 (19) | −0.0248 (2) | −0.00267 (18) |
I1B | 0.0614 (3) | 0.0476 (3) | 0.0631 (3) | −0.0168 (2) | −0.0366 (3) | −0.0039 (2) |
I1B' | 0.0614 (3) | 0.0476 (3) | 0.0631 (3) | −0.0168 (2) | −0.0366 (3) | −0.0039 (2) |
O1A—C1A | 1.446 (9) | O1B—C12B | 1.358 (7) |
O1A—C12A | 1.386 (8) | C1B—O2B | 1.441 (9) |
C1A—O2A | 1.450 (9) | C1B—H1B | 0.971 |
C1A—H1A | 0.972 | C1B—H2B | 0.972 |
C1A—H2A | 0.968 | O2B—C13B | 1.382 (8) |
O2A—C13A | 1.381 (9) | C2B—C13B | 1.374 (10) |
C2A—C13A | 1.345 (10) | C2B—C14B | 1.404 (10) |
C2A—C14A | 1.419 (10) | C2B—H3B | 0.930 |
C2A—H3A | 0.934 | C3B—C4B | 1.523 (10) |
C3A—C4A | 1.483 (11) | C3B—C14B | 1.511 (9) |
C3A—C14A | 1.497 (10) | C3B—H4B | 0.975 |
C3A—H4A | 0.969 | C3B—H5B | 0.982 |
C3A—H5A | 0.974 | C4B—N1B | 1.472 (8) |
C4A—N1A | 1.485 (9) | C4B—H6B | 0.971 |
C4A—H6A | 0.978 | C4B—H7B | 0.967 |
C4A—H7A | 0.967 | N1B—C5B | 1.319 (8) |
N1A—C5A | 1.347 (9) | N1B—C17B | 1.398 (7) |
N1A—C17A | 1.383 (8) | C5B—C15B | 1.409 (9) |
C5A—C15A | 1.396 (9) | C5B—H8B | 0.932 |
C5A—H8A | 0.935 | C6B—C7B | 1.399 (9) |
C6A—C7A | 1.390 (9) | C6B—C15B | 1.398 (9) |
C6A—C15A | 1.420 (9) | C6B—O4B | 1.362 (8) |
C6A—O4A | 1.370 (7) | C7B—C8B | 1.388 (9) |
C7A—C8A | 1.396 (9) | C7B—O3B | 1.359 (8) |
C7A—O3A | 1.360 (8) | C8B—C9B | 1.379 (9) |
C8A—C9A | 1.376 (10) | C8B—H9B | 0.934 |
C8A—H9A | 0.933 | C9B—C16B | 1.420 (8) |
C9A—C16A | 1.403 (9) | C9B—H10B | 0.934 |
C9A—H10A | 0.933 | C10B—C16B | 1.406 (8) |
C10A—C16A | 1.414 (9) | C10B—C17B | 1.379 (8) |
C10A—C17A | 1.371 (8) | C10B—H11B | 0.925 |
C10A—H11A | 0.930 | C11B—C12B | 1.375 (9) |
C11A—C12A | 1.357 (10) | C11B—C18B | 1.419 (8) |
C11A—C18A | 1.418 (9) | C11B—H12B | 0.930 |
C11A—H12A | 0.935 | C12B—C13B | 1.377 (9) |
C12A—C13A | 1.383 (10) | C14B—C18B | 1.393 (9) |
C14A—C18A | 1.381 (9) | C15B—C16B | 1.410 (8) |
C15A—C16A | 1.429 (8) | C17B—C18B | 1.452 (9) |
C17A—C18A | 1.486 (9) | O4B—C20B | 1.395 (9) |
O3A—C19A | 1.421 (9) | O3B—C19B | 1.439 (9) |
O4A—C20A | 1.441 (8) | C19B—H13B | 0.959 |
C19A—H13A | 0.966 | C19B—H14B | 0.966 |
C19A—H14A | 0.960 | C19B—H15B | 0.963 |
C19A—H15A | 0.957 | C20B—C21B | 1.497 (11) |
C20A—C21A | 1.481 (10) | C20B—H16B | 0.963 |
C20A—H16A | 0.980 | C20B—H17B | 0.967 |
C20A—H17A | 0.978 | C21B—H18B | 0.961 |
C21A—H18A | 0.962 | C21B—H19B | 0.955 |
C21A—H19A | 0.962 | C21B—H20B | 0.962 |
C21A—H20A | 0.967 | O5—H21 | 0.916 |
O1B—C1B | 1.443 (8) | O5—H22 | 0.852 |
C1A—O1A—C12A | 105.6 (5) | O1B—C1B—O2B | 106.1 (5) |
O1A—C1A—O2A | 105.9 (5) | O1B—C1B—H1B | 109.9 |
O1A—C1A—H1A | 110.5 | O2B—C1B—H1B | 110.5 |
O2A—C1A—H1A | 110.8 | O1B—C1B—H2B | 109.9 |
O1A—C1A—H2A | 109.7 | O2B—C1B—H2B | 110.6 |
O2A—C1A—H2A | 109.2 | H1B—C1B—H2B | 109.7 |
H1A—C1A—H2A | 110.6 | C1B—O2B—C13B | 104.1 (5) |
C1A—O2A—C13A | 105.2 (5) | C13B—C2B—C14B | 116.8 (6) |
C13A—C2A—C14A | 117.2 (7) | C13B—C2B—H3B | 121.8 |
C13A—C2A—H3A | 121.7 | C14B—C2B—H3B | 121.4 |
C14A—C2A—H3A | 121.1 | C4B—C3B—C14B | 111.8 (6) |
C4A—C3A—C14A | 111.6 (6) | C4B—C3B—H4B | 107.8 |
C4A—C3A—H4A | 109.2 | C14B—C3B—H4B | 109.7 |
C14A—C3A—H4A | 109.2 | C4B—C3B—H5B | 108.5 |
C4A—C3A—H5A | 107.5 | C14B—C3B—H5B | 108.9 |
C14A—C3A—H5A | 109.6 | H4B—C3B—H5B | 110.2 |
H4A—C3A—H5A | 109.8 | C3B—C4B—N1B | 111.1 (5) |
C3A—C4A—N1A | 112.0 (6) | C3B—C4B—H6B | 108.1 |
C3A—C4A—H6A | 108.0 | N1B—C4B—H6B | 109.0 |
N1A—C4A—H6A | 110.1 | C3B—C4B—H7B | 109.5 |
C3A—C4A—H7A | 108.9 | N1B—C4B—H7B | 109.1 |
N1A—C4A—H7A | 107.2 | H6B—C4B—H7B | 110.0 |
H6A—C4A—H7A | 110.7 | C4B—N1B—C5B | 117.3 (5) |
C4A—N1A—C5A | 117.7 (5) | C4B—N1B—C17B | 119.2 (5) |
C4A—N1A—C17A | 119.8 (6) | C5B—N1B—C17B | 123.3 (5) |
C5A—N1A—C17A | 122.2 (6) | N1B—C5B—C15B | 121.7 (6) |
N1A—C5A—C15A | 121.4 (6) | N1B—C5B—H8B | 119.1 |
N1A—C5A—H8A | 119.0 | C15B—C5B—H8B | 119.2 |
C15A—C5A—H8A | 119.6 | C7B—C6B—C15B | 118.8 (6) |
C7A—C6A—C15A | 119.2 (6) | C7B—C6B—O4B | 122.5 (6) |
C7A—C6A—O4A | 122.1 (6) | C15B—C6B—O4B | 118.5 (6) |
C15A—C6A—O4A | 118.7 (6) | C6B—C7B—C8B | 119.7 (6) |
C6A—C7A—C8A | 120.0 (6) | C6B—C7B—O3B | 116.6 (6) |
C6A—C7A—O3A | 116.2 (6) | C8B—C7B—O3B | 123.7 (6) |
C8A—C7A—O3A | 123.8 (6) | C7B—C8B—C9B | 122.1 (6) |
C7A—C8A—C9A | 121.9 (6) | C7B—C8B—H9B | 118.2 |
C7A—C8A—H9A | 118.8 | C9B—C8B—H9B | 119.8 |
C9A—C8A—H9A | 119.3 | C8B—C9B—C16B | 119.6 (5) |
C8A—C9A—C16A | 120.0 (6) | C8B—C9B—H10B | 120.1 |
C8A—C9A—H10A | 120.7 | C16B—C9B—H10B | 120.3 |
C16A—C9A—H10A | 119.3 | C16B—C10B—C17B | 122.9 (5) |
C16A—C10A—C17A | 122.2 (6) | C16B—C10B—H11B | 118.5 |
C16A—C10A—H11A | 118.6 | C17B—C10B—H11B | 118.6 |
C17A—C10A—H11A | 119.2 | C12B—C11B—C18B | 117.0 (6) |
C12A—C11A—C18A | 116.5 (6) | C12B—C11B—H12B | 121.4 |
C12A—C11A—H12A | 121.4 | C18B—C11B—H12B | 121.5 |
C18A—C11A—H12A | 122.1 | C11B—C12B—O1B | 128.0 (6) |
O1A—C12A—C11A | 128.2 (6) | C11B—C12B—C13B | 121.7 (6) |
O1A—C12A—C13A | 109.0 (6) | O1B—C12B—C13B | 110.1 (6) |
C11A—C12A—C13A | 122.8 (6) | O2B—C13B—C12B | 109.4 (6) |
C12A—C13A—O2A | 110.2 (6) | O2B—C13B—C2B | 127.9 (6) |
C12A—C13A—C2A | 122.0 (7) | C12B—C13B—C2B | 122.6 (6) |
O2A—C13A—C2A | 127.8 (7) | C3B—C14B—C2B | 120.1 (6) |
C3A—C14A—C2A | 120.7 (6) | C3B—C14B—C18B | 118.4 (6) |
C3A—C14A—C18A | 118.5 (6) | C2B—C14B—C18B | 121.3 (6) |
C2A—C14A—C18A | 120.8 (6) | C5B—C15B—C6B | 120.5 (6) |
C6A—C15A—C5A | 121.7 (6) | C5B—C15B—C16B | 117.5 (6) |
C6A—C15A—C16A | 120.2 (6) | C6B—C15B—C16B | 122.0 (6) |
C5A—C15A—C16A | 118.2 (6) | C9B—C16B—C15B | 117.9 (6) |
C15A—C16A—C10A | 117.8 (6) | C9B—C16B—C10B | 123.8 (5) |
C15A—C16A—C9A | 118.7 (6) | C15B—C16B—C10B | 118.3 (5) |
C10A—C16A—C9A | 123.4 (6) | N1B—C17B—C10B | 116.0 (5) |
N1A—C17A—C10A | 118.1 (6) | N1B—C17B—C18B | 119.4 (5) |
N1A—C17A—C18A | 117.6 (5) | C10B—C17B—C18B | 124.6 (5) |
C10A—C17A—C18A | 124.3 (6) | C17B—C18B—C11B | 118.4 (6) |
C17A—C18A—C11A | 118.5 (6) | C17B—C18B—C14B | 121.0 (6) |
C17A—C18A—C14A | 120.8 (6) | C11B—C18B—C14B | 120.5 (6) |
C11A—C18A—C14A | 120.7 (6) | C6B—O4B—C20B | 117.1 (6) |
C7A—O3A—C19A | 117.2 (5) | C7B—O3B—C19B | 116.7 (5) |
C6A—O4A—C20A | 113.4 (5) | O3B—C19B—H13B | 108.7 |
O3A—C19A—H13A | 109.4 | O3B—C19B—H14B | 109.9 |
O3A—C19A—H14A | 109.1 | H13B—C19B—H14B | 109.9 |
H13A—C19A—H14A | 110.2 | O3B—C19B—H15B | 109.9 |
O3A—C19A—H15A | 109.5 | H13B—C19B—H15B | 109.2 |
H13A—C19A—H15A | 109.3 | H14B—C19B—H15B | 109.2 |
H14A—C19A—H15A | 109.3 | O4B—C20B—C21B | 110.0 (7) |
O4A—C20A—C21A | 108.7 (6) | O4B—C20B—H16B | 109.3 |
O4A—C20A—H16A | 107.8 | C21B—C20B—H16B | 109.6 |
C21A—C20A—H16A | 109.0 | O4B—C20B—H17B | 109.0 |
O4A—C20A—H17A | 110.6 | C21B—C20B—H17B | 109.4 |
C21A—C20A—H17A | 110.7 | H16B—C20B—H17B | 109.5 |
H16A—C20A—H17A | 109.9 | C20B—C21B—H18B | 109.3 |
C20A—C21A—H18A | 109.8 | C20B—C21B—H19B | 109.1 |
C20A—C21A—H19A | 109.2 | H18B—C21B—H19B | 109.7 |
H18A—C21A—H19A | 109.5 | C20B—C21B—H20B | 109.1 |
C20A—C21A—H20A | 109.4 | H18B—C21B—H20B | 109.8 |
H18A—C21A—H20A | 109.9 | H19B—C21B—H20B | 109.7 |
H19A—C21A—H20A | 109.1 | H21—O5—H22 | 90.7 |
C1B—O1B—C12B | 104.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H10A···O5 | 0.93 | 2.47 | 3.358 (11) | 159 |
C21B—H20B···O1Bi | 0.96 | 2.51 | 3.466 (11) | 177 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | 2C21H20NO4+·2I−·H2O |
Mr | 972.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 93 |
a, b, c (Å) | 11.036 (3), 13.449 (4), 14.086 (4) |
α, β, γ (°) | 80.442 (6), 71.121 (5), 76.875 (5) |
V (Å3) | 1916.8 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.70 |
Crystal size (mm) | 1.00 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID II image plate diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.469, 0.712 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 50086, 8751, 4563 |
Rint | 0.101 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.195, 0.96 |
No. of reflections | 8751 |
No. of parameters | 502 |
No. of restraints | 12 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 1.75, −2.26 |
Computer programs: CrystalClear (Rigaku, 2009), HKL-2000 (Otwinowski & Minor, 1997), CrystalStructure (Rigaku, 2009) and SIR2004 (Burla et al., 2005), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H10A···O5 | 0.93 | 2.47 | 3.358 (11) | 159 |
C21B—H20B···O1Bi | 0.96 | 2.51 | 3.466 (11) | 177 |
Symmetry code: (i) x, y+1, z. |
The title compound, a derivative of the natural product berberine, is of interest with respect to its anti-parasite activity and biological properties Chen et al. (2009). Of particular interest is the discovery that berberine and its analogs inhibit the growth of strains of the parasites Leishmania (Nkwengoua et al., 2009, Acero et al., 1995, Ghosh et al., 1985), Trypanosoma (Nkwengoua et al., 2009), and Plasmodium (Wright et al., 2000, Iwasa et al., 1998, Sheng et al., 1997, McCall et al., 1994). Based on these findings and in our continued effort to characterize compounds that may inhibit the life cycle of the parasite Toxoplasma gondii we have synthesized the 9-ethyl analog of berberine.
The title compound, 2(C21H20NO4+), 2(I-), H2O, crystallizes in the P-1 space group with two independent molecules in the unit cell. A solvent water molecule occupies the lattice at H-bonding distance from the disordered iodide (1.94 & 0.06) anions [O5—I1A 3.509 (6) and O5—I1B 3.600 (6) Å]. The compound crystallizes with a slightly twisted planar structure due to the dihydropyridine moiety, which results in torsion angles of 17.7 (5)° (C15A/C16A/C11A/C2A) and 6.1 (5)° (C15B/C16B/C11B/C2B) between the planes of the isoquiniline and benzodioxole moieties for molecules A and B respectively. The molecules are layered in the crystal lattice with normal π—π stacking distances between centroids of the rings of molecules A and B of 3.571 (4)Å (rings C6A/C7A/C8A/C9A/C15A/C16A to C2B/C11B/C12B/C13B/C14B/C18B), 3.839 (4)Å (rings N1A/C5A/C10A/C15A/C16A/C17A to N1B/C5B/C10B/C15B/C16B/C17B), and 3.686 (4)Å (rings C2A/C11A/C12A/C13A/C14A/C18A to C6B/C7B/C8B/C9B/C15B/C16B). Identical molecules neighboring each other are located at further stacking distances with the closest controid distance of 3.815 (4)Å between molecules A to A and 3.949 (4)Å between molecules B to B.