Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054420/lh2272sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054420/lh2272Isup2.hkl |
CCDC reference: 633923
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C19
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H24ClN32+·2Cl−·H2O | F(000) = 904 |
Mr = 430.79 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 31509 reflections |
a = 15.3427 (8) Å | θ = 1.4–27.2° |
b = 6.8703 (2) Å | µ = 0.45 mm−1 |
c = 21.7329 (11) Å | T = 296 K |
β = 111.355 (4)° | Prism, colourless |
V = 2133.56 (18) Å3 | 0.50 × 0.34 × 0.17 mm |
Z = 4 |
Stoe IPDS-2 diffractometer | 4634 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3223 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.061 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 1.4° |
ω scans | h = −19→19 |
Absorption correction: integration (XRED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.808, Tmax = 0.928 | l = −27→27 |
39631 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0666P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
4634 reflections | Δρmax = 0.24 e Å−3 |
253 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0127 (13) |
Experimental. 13C-NMR (D2O): δ 22.68, 42.90, 50.34, 52.09, 54.68, 112.86, 114.00, 127.73, 129.25, 130.04, 131.11, 134.57, 141.74. Analysis calculated for C20H26N3OCl3: C 55.75, H 6.04, N 9.76%; found: C 55.63, H 5.58, N 9.80%. 1H-NMR (D2O): δ 1.5–2.1 (m, ring methylene, 4H), 3.0 (m, ring methylene, 2H), 3.4 (t, ring methylene, 2H), 4.0 (t, pyrrolidine-CH2CH2–,2H), 4.9 (t, pyrrolidine-CH2CH2–, 2H), 5.8 (s, PhCH2–, 2H), 6.8–7.8 (m, Ar—H, 8H), 9.7 (s, pyrrolidine-1H). 13C-NMR (D2O): δ 22.68, 42.90, 50.34, 52.09, 54.68, 112.86, 114.00, 127.73, 129.25, 130.04, 131.11, 134.57, 141.74. Analysis calculated for C20H26N3OCl3: C 55.75, H 6.04, N 9.76%; found: C 55.63, H 5.58, N 9.80%. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.92948 (4) | 0.58903 (9) | 0.25253 (3) | 0.0801 (2) | |
N1 | 0.60810 (9) | −0.12368 (18) | 0.19517 (6) | 0.0439 (4) | |
N2 | 0.45845 (9) | −0.09061 (19) | 0.13970 (6) | 0.0438 (4) | |
N3 | 0.20907 (10) | −0.1801 (2) | 0.03254 (7) | 0.0533 (4) | |
C1 | 0.54208 (11) | −0.1117 (2) | 0.13534 (8) | 0.0459 (5) | |
C2 | 0.47005 (11) | −0.0911 (2) | 0.20636 (7) | 0.0421 (4) | |
C3 | 0.40623 (11) | −0.0783 (2) | 0.23813 (8) | 0.0470 (5) | |
C4 | 0.44348 (13) | −0.0856 (2) | 0.30641 (8) | 0.0511 (5) | |
C5 | 0.53949 (12) | −0.1041 (2) | 0.34150 (8) | 0.0501 (5) | |
C6 | 0.60266 (12) | −0.1163 (2) | 0.31014 (8) | 0.0464 (5) | |
C7 | 0.56531 (10) | −0.1094 (2) | 0.24141 (7) | 0.0412 (4) | |
C8 | 0.70905 (11) | −0.1528 (2) | 0.21000 (9) | 0.0497 (5) | |
C9 | 0.76251 (11) | 0.0369 (2) | 0.22314 (8) | 0.0460 (5) | |
C10 | 0.83324 (12) | 0.0735 (3) | 0.28300 (9) | 0.0567 (5) | |
C11 | 0.88393 (13) | 0.2438 (3) | 0.29322 (9) | 0.0628 (6) | |
C12 | 0.86369 (12) | 0.3775 (3) | 0.24236 (9) | 0.0541 (5) | |
C13 | 0.79309 (13) | 0.3463 (3) | 0.18330 (9) | 0.0566 (6) | |
C14 | 0.74255 (12) | 0.1751 (3) | 0.17389 (8) | 0.0539 (5) | |
C15 | 0.37004 (11) | −0.0589 (2) | 0.08390 (8) | 0.0493 (5) | |
C16 | 0.30607 (12) | −0.2337 (3) | 0.07377 (8) | 0.0530 (5) | |
C17 | 0.19630 (15) | −0.1083 (4) | −0.03468 (9) | 0.0752 (7) | |
C18 | 0.09488 (19) | −0.1451 (6) | −0.07314 (14) | 0.1111 (12) | |
C19 | 0.0763 (2) | −0.3353 (6) | −0.0473 (2) | 0.1361 (15) | |
C20 | 0.13971 (16) | −0.3431 (4) | 0.02346 (13) | 0.0847 (9) | |
O1 | 0.55265 (15) | 0.2402 (3) | 0.03085 (9) | 0.0815 (6) | |
Cl2 | 0.66000 (4) | 0.64696 (8) | 0.03799 (3) | 0.0728 (2) | |
Cl3 | 0.17213 (4) | 0.15216 (8) | 0.10900 (3) | 0.0730 (2) | |
H1 | 0.55290 | −0.11720 | 0.09600 | 0.0550* | |
H3 | 0.34230 | −0.06570 | 0.21480 | 0.0560* | |
H3A | 0.19170 | −0.08190 | 0.05370 | 0.0640* | |
H4 | 0.40330 | −0.07780 | 0.32970 | 0.0610* | |
H5 | 0.56140 | −0.10830 | 0.38740 | 0.0600* | |
H6 | 0.66660 | −0.12840 | 0.33350 | 0.0560* | |
H8A | 0.71750 | −0.21810 | 0.17300 | 0.0600* | |
H8B | 0.73440 | −0.23640 | 0.24840 | 0.0600* | |
H10 | 0.84680 | −0.01790 | 0.31680 | 0.0680* | |
H11 | 0.93110 | 0.26850 | 0.33380 | 0.0750* | |
H13 | 0.77910 | 0.43870 | 0.14980 | 0.0680* | |
H14 | 0.69430 | 0.15280 | 0.13370 | 0.0650* | |
H15A | 0.38300 | −0.03580 | 0.04410 | 0.0590* | |
H15B | 0.33900 | 0.05540 | 0.09230 | 0.0590* | |
H16A | 0.32760 | −0.33720 | 0.05240 | 0.0640* | |
H16B | 0.30790 | −0.28130 | 0.11630 | 0.0640* | |
H17A | 0.23560 | −0.17960 | −0.05320 | 0.0900* | |
H17B | 0.21080 | 0.02930 | −0.03390 | 0.0900* | |
H18A | 0.05630 | −0.04300 | −0.06560 | 0.1330* | |
H18B | 0.08290 | −0.15300 | −0.12010 | 0.1330* | |
H19A | 0.08950 | −0.44210 | −0.07180 | 0.1630* | |
H19B | 0.01150 | −0.34360 | −0.05110 | 0.1630* | |
H20A | 0.17160 | −0.46760 | 0.03360 | 0.1020* | |
H20B | 0.10450 | −0.32490 | 0.05210 | 0.1020* | |
HW1 | 0.497 (2) | 0.261 (4) | 0.0138 (13) | 0.087 (9)* | |
HW2 | 0.582 (2) | 0.348 (5) | 0.0309 (15) | 0.103 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0739 (3) | 0.0759 (3) | 0.0881 (4) | −0.0267 (3) | 0.0265 (3) | −0.0033 (3) |
N1 | 0.0414 (6) | 0.0460 (7) | 0.0450 (7) | −0.0011 (5) | 0.0167 (5) | −0.0009 (5) |
N2 | 0.0425 (6) | 0.0486 (7) | 0.0381 (6) | 0.0005 (5) | 0.0121 (5) | 0.0003 (5) |
N3 | 0.0459 (7) | 0.0610 (8) | 0.0486 (7) | −0.0025 (6) | 0.0119 (6) | −0.0055 (6) |
C1 | 0.0491 (8) | 0.0483 (8) | 0.0421 (8) | −0.0026 (6) | 0.0189 (7) | −0.0024 (6) |
C2 | 0.0452 (8) | 0.0388 (7) | 0.0424 (7) | −0.0010 (6) | 0.0160 (6) | 0.0006 (6) |
C3 | 0.0447 (8) | 0.0471 (8) | 0.0520 (9) | −0.0002 (6) | 0.0208 (7) | 0.0000 (7) |
C4 | 0.0629 (10) | 0.0460 (8) | 0.0531 (9) | −0.0024 (7) | 0.0314 (8) | −0.0011 (7) |
C5 | 0.0660 (10) | 0.0439 (8) | 0.0409 (8) | −0.0011 (7) | 0.0199 (7) | 0.0002 (6) |
C6 | 0.0495 (8) | 0.0423 (8) | 0.0431 (8) | −0.0016 (6) | 0.0116 (7) | 0.0000 (6) |
C7 | 0.0433 (7) | 0.0394 (7) | 0.0417 (7) | −0.0002 (6) | 0.0165 (6) | −0.0001 (6) |
C8 | 0.0428 (8) | 0.0538 (9) | 0.0542 (9) | 0.0022 (7) | 0.0196 (7) | −0.0010 (7) |
C9 | 0.0405 (8) | 0.0531 (9) | 0.0467 (8) | 0.0018 (6) | 0.0188 (6) | 0.0000 (7) |
C10 | 0.0517 (9) | 0.0644 (10) | 0.0482 (9) | −0.0027 (8) | 0.0114 (7) | 0.0080 (8) |
C11 | 0.0549 (10) | 0.0743 (12) | 0.0508 (9) | −0.0116 (9) | 0.0093 (8) | 0.0003 (9) |
C12 | 0.0469 (8) | 0.0582 (10) | 0.0607 (10) | −0.0032 (7) | 0.0237 (8) | −0.0041 (8) |
C13 | 0.0546 (9) | 0.0615 (10) | 0.0547 (10) | −0.0003 (8) | 0.0210 (8) | 0.0088 (8) |
C14 | 0.0483 (9) | 0.0636 (10) | 0.0454 (8) | −0.0033 (7) | 0.0119 (7) | 0.0017 (7) |
C15 | 0.0456 (8) | 0.0539 (9) | 0.0420 (8) | 0.0011 (7) | 0.0083 (7) | 0.0036 (7) |
C16 | 0.0512 (9) | 0.0522 (9) | 0.0480 (8) | 0.0027 (7) | 0.0090 (7) | −0.0017 (7) |
C17 | 0.0598 (11) | 0.1088 (17) | 0.0463 (9) | 0.0042 (11) | 0.0065 (8) | 0.0088 (10) |
C18 | 0.0628 (14) | 0.176 (3) | 0.0695 (15) | 0.0141 (17) | −0.0055 (12) | 0.0042 (17) |
C19 | 0.0754 (18) | 0.150 (3) | 0.135 (3) | −0.0316 (19) | −0.0189 (18) | −0.019 (2) |
C20 | 0.0648 (13) | 0.0874 (16) | 0.0922 (16) | −0.0233 (11) | 0.0172 (12) | −0.0103 (12) |
O1 | 0.0774 (11) | 0.0797 (12) | 0.0807 (10) | 0.0131 (10) | 0.0209 (9) | 0.0043 (8) |
Cl2 | 0.0721 (3) | 0.0789 (3) | 0.0606 (3) | 0.0031 (2) | 0.0162 (2) | 0.0025 (2) |
Cl3 | 0.0590 (3) | 0.0802 (3) | 0.0820 (3) | 0.0003 (2) | 0.0284 (2) | −0.0227 (3) |
Cl1—C12 | 1.737 (2) | C17—C18 | 1.496 (4) |
O1—HW1 | 0.81 (3) | C18—C19 | 1.490 (6) |
O1—HW2 | 0.87 (3) | C19—C20 | 1.492 (5) |
N1—C1 | 1.328 (2) | C1—H1 | 0.9300 |
N1—C7 | 1.390 (2) | C3—H3 | 0.9300 |
N1—C8 | 1.476 (2) | C4—H4 | 0.9300 |
N2—C1 | 1.329 (2) | C5—H5 | 0.9300 |
N2—C15 | 1.470 (2) | C6—H6 | 0.9300 |
N2—C2 | 1.3938 (19) | C8—H8A | 0.9700 |
N3—C17 | 1.486 (2) | C8—H8B | 0.9700 |
N3—C20 | 1.508 (3) | C10—H10 | 0.9300 |
N3—C16 | 1.477 (2) | C11—H11 | 0.9300 |
N3—H3A | 0.9100 | C13—H13 | 0.9300 |
C2—C3 | 1.391 (2) | C14—H14 | 0.9300 |
C2—C7 | 1.386 (2) | C15—H15B | 0.9700 |
C3—C4 | 1.383 (2) | C15—H15A | 0.9700 |
C4—C5 | 1.396 (3) | C16—H16A | 0.9700 |
C5—C6 | 1.376 (3) | C16—H16B | 0.9700 |
C6—C7 | 1.392 (2) | C17—H17A | 0.9700 |
C8—C9 | 1.511 (2) | C17—H17B | 0.9700 |
C9—C10 | 1.380 (2) | C18—H18B | 0.9700 |
C9—C14 | 1.379 (2) | C18—H18A | 0.9700 |
C10—C11 | 1.377 (3) | C19—H19A | 0.9700 |
C11—C12 | 1.383 (3) | C19—H19B | 0.9700 |
C12—C13 | 1.362 (3) | C20—H20B | 0.9700 |
C13—C14 | 1.382 (3) | C20—H20A | 0.9700 |
C15—C16 | 1.516 (3) | ||
Cl1···C8i | 3.6279 (19) | C6···H8B | 2.9200 |
Cl1···C11ii | 3.520 (2) | C6···H16Biv | 2.8500 |
Cl2···O1 | 3.219 (2) | C8···H6 | 2.9900 |
Cl2···O1iii | 3.151 (2) | C13···H18Bvi | 3.0300 |
Cl2···C1i | 3.6451 (18) | C13···H17Avi | 2.9300 |
Cl3···C16 | 3.603 (2) | C13···H4iv | 2.9700 |
Cl3···N3 | 2.9965 (16) | C14···H17Avi | 2.7600 |
Cl3···C15 | 3.5814 (19) | C14···H4iv | 2.7900 |
Cl3···C6iv | 3.6243 (19) | C15···H17A | 3.0600 |
Cl1···H18Bv | 2.9400 | C15···H17B | 2.8900 |
Cl2···H17Biii | 3.0000 | C15···H3 | 3.0300 |
Cl2···HW1iii | 2.34 (3) | C17···H15B | 3.0500 |
Cl2···H15Aiii | 3.1500 | C17···H15A | 2.8000 |
Cl2···H16Avi | 2.9500 | H1···O1 | 2.8300 |
Cl2···H1i | 2.9000 | H1···Cl2x | 2.9000 |
Cl2···H5vii | 3.0800 | H1···O1vi | 2.7700 |
Cl2···H8Ai | 2.8900 | H1···HW1vi | 2.4300 |
Cl2···H13 | 2.8400 | H1···H15A | 2.5000 |
Cl2···HW2 | 2.35 (3) | H1···H8A | 2.5700 |
Cl3···H19Bviii | 2.9400 | HW1···H1vi | 2.4300 |
Cl3···H10iv | 2.8600 | HW1···Cl2iii | 2.34 (3) |
Cl3···H15B | 2.7900 | HW2···Cl2 | 2.35 (3) |
Cl3···H20Ai | 3.0800 | H3···H16B | 2.5000 |
Cl3···H3A | 2.0900 | H3···C15 | 3.0300 |
Cl3···H6iv | 2.7800 | H3A···Cl3 | 2.0900 |
Cl3···H8Biv | 3.0000 | H3A···H15B | 2.3100 |
O1···C1 | 3.361 (3) | H4···C13ix | 2.9700 |
O1···Cl2iii | 3.151 (2) | H4···C14ix | 2.7900 |
O1···C15vi | 3.366 (3) | H5···Cl2xii | 3.0800 |
O1···Cl2 | 3.219 (2) | H5···H16Aiv | 2.5400 |
O1···H15Avi | 2.6000 | H6···C8 | 2.9900 |
O1···H14 | 2.5600 | H6···H16Biv | 2.5900 |
O1···H1vi | 2.7700 | H6···H8B | 2.5400 |
O1···H1 | 2.8300 | H6···Cl3ix | 2.7800 |
N1···C4ix | 3.2679 (19) | H8A···H1 | 2.5700 |
N2···C5iv | 3.3661 (19) | H8A···Cl2x | 2.8900 |
N3···Cl3 | 2.9965 (16) | H8B···H6 | 2.5400 |
N1···H14 | 2.9000 | H8B···H10 | 2.3600 |
C1···C4ix | 3.471 (2) | H8B···C6 | 2.9200 |
C1···O1 | 3.361 (3) | H8B···Cl3ix | 3.0000 |
C1···C14 | 3.488 (3) | H10···Cl3ix | 2.8600 |
C1···Cl2x | 3.6451 (18) | H10···H8B | 2.3600 |
C2···C6iv | 3.424 (2) | H13···Cl2 | 2.8400 |
C2···C5iv | 3.491 (2) | H14···N1 | 2.9000 |
C3···C7iv | 3.260 (2) | H14···C1 | 2.9700 |
C3···C16 | 3.502 (2) | H14···O1 | 2.5600 |
C3···C6iv | 3.330 (2) | H14···H17Avi | 2.3700 |
C4···C14ix | 3.453 (3) | H15A···H1 | 2.5000 |
C4···C1iv | 3.471 (2) | H15A···C17 | 2.8000 |
C4···C7iv | 3.421 (2) | H15A···O1vi | 2.6000 |
C4···N1iv | 3.2679 (19) | H15A···Cl2iii | 3.1500 |
C5···N2ix | 3.3661 (19) | H15B···H3A | 2.3100 |
C5···C16iv | 3.508 (3) | H15B···C5iv | 3.0100 |
C5···C2ix | 3.491 (2) | H15B···C17 | 3.0500 |
C5···C15ix | 3.561 (2) | H15B···C3 | 3.0900 |
C6···Cl3ix | 3.6243 (19) | H15B···Cl3 | 2.7900 |
C6···C16iv | 3.559 (2) | H15B···C6iv | 3.0000 |
C6···C3ix | 3.330 (2) | H16A···H17A | 2.4600 |
C6···C2ix | 3.424 (2) | H16A···H20A | 2.4500 |
C7···C4ix | 3.421 (2) | H16A···Cl2vi | 2.9500 |
C7···C3ix | 3.260 (2) | H16A···C5ix | 3.0700 |
C8···Cl1x | 3.6279 (19) | H16A···H5ix | 2.5400 |
C11···Cl1xi | 3.520 (2) | H16B···C2 | 2.8600 |
C14···C17vi | 3.509 (3) | H16B···C3 | 2.8800 |
C14···C1 | 3.488 (3) | H16B···H3 | 2.5000 |
C14···C4iv | 3.453 (3) | H16B···H20A | 2.5500 |
C15···Cl3 | 3.5814 (19) | H16B···H6ix | 2.5900 |
C15···O1vi | 3.366 (3) | H16B···C6ix | 2.8500 |
C15···C5iv | 3.561 (2) | H17A···C13vi | 2.9300 |
C16···C5ix | 3.508 (3) | H17A···H16A | 2.4600 |
C16···C3 | 3.502 (2) | H17A···C15 | 3.0600 |
C16···Cl3 | 3.603 (2) | H17A···C14vi | 2.7600 |
C16···C6ix | 3.559 (2) | H17A···H14vi | 2.3700 |
C17···C14vi | 3.509 (3) | H17B···C15 | 2.8900 |
C1···H14 | 2.9700 | H17B···Cl2iii | 3.0000 |
C2···H16B | 2.8600 | H18B···Cl1xiii | 2.9400 |
C3···H15B | 3.0900 | H18B···C13vi | 3.0300 |
C3···H16B | 2.8800 | H19B···Cl3viii | 2.9400 |
C5···H16Aiv | 3.0700 | H20A···Cl3x | 3.0800 |
C5···H15Bix | 3.0100 | H20A···H16A | 2.4500 |
C6···H15Bix | 3.0000 | H20A···H16B | 2.5500 |
HW1—O1—HW2 | 108 (3) | C4—C5—H5 | 119.00 |
C1—N1—C8 | 125.99 (14) | C6—C5—H5 | 119.00 |
C7—N1—C8 | 125.88 (13) | C7—C6—H6 | 122.00 |
C1—N1—C7 | 108.11 (14) | C5—C6—H6 | 122.00 |
C1—N2—C2 | 108.23 (13) | N1—C8—H8A | 109.00 |
C1—N2—C15 | 125.63 (13) | N1—C8—H8B | 109.00 |
C2—N2—C15 | 126.03 (14) | C9—C8—H8B | 109.00 |
C16—N3—C17 | 114.97 (16) | H8A—C8—H8B | 108.00 |
C16—N3—C20 | 113.67 (16) | C9—C8—H8A | 109.00 |
C17—N3—C20 | 106.49 (16) | C11—C10—H10 | 120.00 |
C17—N3—H3A | 107.00 | C9—C10—H10 | 120.00 |
C20—N3—H3A | 107.00 | C10—C11—H11 | 120.00 |
C16—N3—H3A | 107.00 | C12—C11—H11 | 120.00 |
N1—C1—N2 | 110.43 (14) | C14—C13—H13 | 121.00 |
N2—C2—C7 | 106.35 (14) | C12—C13—H13 | 121.00 |
N2—C2—C3 | 132.00 (15) | C9—C14—H14 | 119.00 |
C3—C2—C7 | 121.66 (14) | C13—C14—H14 | 119.00 |
C2—C3—C4 | 116.08 (16) | N2—C15—H15B | 109.00 |
C3—C4—C5 | 122.06 (18) | C16—C15—H15A | 109.00 |
C4—C5—C6 | 121.91 (15) | C16—C15—H15B | 109.00 |
C5—C6—C7 | 116.14 (16) | H15A—C15—H15B | 108.00 |
N1—C7—C6 | 130.93 (15) | N2—C15—H15A | 109.00 |
C2—C7—C6 | 122.17 (15) | N3—C16—H16B | 110.00 |
N1—C7—C2 | 106.87 (13) | C15—C16—H16A | 110.00 |
N1—C8—C9 | 112.25 (12) | N3—C16—H16A | 110.00 |
C10—C9—C14 | 118.83 (16) | H16A—C16—H16B | 108.00 |
C8—C9—C10 | 121.45 (15) | C15—C16—H16B | 110.00 |
C8—C9—C14 | 119.69 (15) | N3—C17—H17A | 111.00 |
C9—C10—C11 | 120.71 (17) | N3—C17—H17B | 111.00 |
C10—C11—C12 | 119.09 (18) | C18—C17—H17B | 111.00 |
Cl1—C12—C11 | 120.21 (15) | H17A—C17—H17B | 109.00 |
Cl1—C12—C13 | 118.53 (15) | C18—C17—H17A | 111.00 |
C11—C12—C13 | 121.26 (19) | C17—C18—H18B | 111.00 |
C12—C13—C14 | 118.96 (18) | C19—C18—H18A | 111.00 |
C9—C14—C13 | 121.12 (16) | C19—C18—H18B | 111.00 |
N2—C15—C16 | 110.90 (13) | H18A—C18—H18B | 109.00 |
N3—C16—C15 | 110.29 (15) | C17—C18—H18A | 111.00 |
N3—C17—C18 | 103.4 (2) | C18—C19—H19B | 111.00 |
C17—C18—C19 | 103.9 (3) | C20—C19—H19A | 111.00 |
C18—C19—C20 | 106.1 (3) | C18—C19—H19A | 110.00 |
N3—C20—C19 | 105.8 (2) | H19A—C19—H19B | 109.00 |
N2—C1—H1 | 125.00 | C20—C19—H19B | 110.00 |
N1—C1—H1 | 125.00 | N3—C20—H20A | 111.00 |
C2—C3—H3 | 122.00 | N3—C20—H20B | 111.00 |
C4—C3—H3 | 122.00 | C19—C20—H20B | 111.00 |
C5—C4—H4 | 119.00 | H20A—C20—H20B | 109.00 |
C3—C4—H4 | 119.00 | C19—C20—H20A | 111.00 |
C7—N1—C1—N2 | −0.07 (17) | N2—C2—C7—N1 | −1.28 (15) |
C8—N1—C1—N2 | 178.32 (13) | C3—C2—C7—N1 | 178.39 (13) |
C7—N1—C8—C9 | −85.98 (18) | N2—C2—C7—C6 | −179.58 (13) |
C1—N1—C7—C6 | 178.96 (15) | C2—C3—C4—C5 | 0.2 (2) |
C1—N1—C7—C2 | 0.86 (16) | C3—C4—C5—C6 | −0.1 (2) |
C8—N1—C7—C2 | −177.53 (13) | C4—C5—C6—C7 | −0.1 (2) |
C8—N1—C7—C6 | 0.6 (2) | C5—C6—C7—C2 | 0.1 (2) |
C1—N1—C8—C9 | 95.91 (18) | C5—C6—C7—N1 | −177.79 (14) |
C15—N2—C1—N1 | 175.45 (13) | N1—C8—C9—C14 | −62.7 (2) |
C2—N2—C1—N1 | −0.75 (16) | N1—C8—C9—C10 | 119.25 (18) |
C15—N2—C2—C3 | 5.5 (2) | C8—C9—C14—C13 | −176.98 (18) |
C1—N2—C2—C7 | 1.26 (16) | C8—C9—C10—C11 | 177.25 (18) |
C1—N2—C2—C3 | −178.36 (15) | C14—C9—C10—C11 | −0.8 (3) |
C2—N2—C15—C16 | −72.28 (19) | C10—C9—C14—C13 | 1.2 (3) |
C1—N2—C15—C16 | 112.18 (17) | C9—C10—C11—C12 | −0.7 (3) |
C15—N2—C2—C7 | −174.92 (13) | C10—C11—C12—C13 | 1.9 (3) |
C20—N3—C16—C15 | −176.51 (16) | C10—C11—C12—Cl1 | −177.35 (16) |
C16—N3—C17—C18 | 157.1 (2) | C11—C12—C13—C14 | −1.6 (3) |
C17—N3—C16—C15 | 60.4 (2) | Cl1—C12—C13—C14 | 177.66 (16) |
C20—N3—C17—C18 | 30.3 (3) | C12—C13—C14—C9 | 0.1 (3) |
C17—N3—C20—C19 | −10.9 (3) | N2—C15—C16—N3 | 162.79 (13) |
C16—N3—C20—C19 | −138.5 (2) | N3—C17—C18—C19 | −38.2 (3) |
N2—C2—C3—C4 | 179.36 (14) | C17—C18—C19—C20 | 31.8 (3) |
C3—C2—C7—C6 | 0.1 (2) | C18—C19—C20—N3 | −13.0 (3) |
C7—C2—C3—C4 | −0.2 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, −y+1/2, z+1/2; (vi) −x+1, −y, −z; (vii) x, −y+1/2, z−1/2; (viii) −x, −y, −z; (ix) −x+1, y−1/2, −z+1/2; (x) x, y−1, z; (xi) −x+2, y−1/2, −z+1/2; (xii) x, −y+1/2, z+1/2; (xiii) x−1, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HW1···Cl2iii | 0.81 (3) | 2.34 (3) | 3.151 (2) | 174 (3) |
O1—HW2···Cl2 | 0.87 (3) | 2.35 (3) | 3.219 (2) | 176 (3) |
N3—H3A···Cl3 | 0.91 | 2.09 | 2.9965 (16) | 172 |
C6—H6···Cl3ix | 0.93 | 2.78 | 3.6243 (19) | 152 |
C14—H14···O1 | 0.93 | 2.56 | 3.429 (3) | 156 |
C15—H15B···Cl3 | 0.97 | 2.79 | 3.5814 (19) | 139 |
Symmetry codes: (iii) −x+1, −y+1, −z; (ix) −x+1, y−1/2, −z+1/2. |
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