Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022689/wn2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022689/wn2037Isup2.hkl |
CCDC reference: 613843
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C21H30Cl2N4O | F(000) = 904 |
Mr = 425.39 | Dx = 1.200 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2871 reflections |
a = 9.9134 (17) Å | θ = 2.3–21.7° |
b = 19.373 (3) Å | µ = 0.29 mm−1 |
c = 12.378 (2) Å | T = 294 K |
β = 98.037 (3)° | Block, colourless |
V = 2353.9 (7) Å3 | 0.54 × 0.40 × 0.38 mm |
Z = 4 |
Bruker SMART 1000 CCD area-detector diffractometer | 4796 independent reflections |
Radiation source: fine-focus sealed tube | 2364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.840, Tmax = 0.895 | k = −24→14 |
13049 measured reflections | l = −15→15 |
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0569P)2 + 0.7546P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
4796 reflections | Δρmax = 0.25 e Å−3 |
281 parameters | Δρmin = −0.26 e Å−3 |
30 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0197 (15) |
Experimental. 1H NMR (CDCl3, δ, p.p.m.): 0.93 (t, 3H), 1.43 (s, 18H), 1.64 (t, 2H), 3.54 (t, 2H), 4.69 (s, 2H), 5.21 (s, 1H), 7.13 (s, 2H) 13C NMR (CDCl3, δ, p.p.m.):11.32 (1 C), 20.25 (1 C), 30.31 (6 C), 34.38 (2 C), 48.99 (1 C), 51.11 (1 C), 125.40 (2 C), 126.56 (1 C), 136.29 (2 C), 153.72 (1 C), 164.82 (1 C), 170.16 (2 C) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | Occ. (<1) | |
Cl1 | −0.41617 (8) | 0.16672 (5) | 0.63713 (7) | 0.0813 (3) | |
Cl2 | 0.02511 (12) | 0.21933 (8) | 0.89709 (8) | 0.1280 (5) | |
N1 | −0.1936 (2) | 0.20394 (11) | 0.56797 (18) | 0.0541 (6) | |
N2 | −0.1894 (3) | 0.19283 (13) | 0.7601 (2) | 0.0710 (7) | |
N3 | 0.0105 (2) | 0.22911 (13) | 0.6891 (2) | 0.0663 (7) | |
N4 | 0.0016 (2) | 0.24067 (11) | 0.50302 (19) | 0.0575 (6) | |
O1 | −0.00452 (19) | −0.03721 (10) | 0.23344 (18) | 0.0731 (6) | |
H1 | 0.0057 | −0.0866 | 0.2616 | 0.110* | |
C1 | −0.0616 (3) | 0.22433 (13) | 0.5871 (2) | 0.0537 (7) | |
C2 | −0.2466 (3) | 0.19023 (13) | 0.6565 (2) | 0.0573 (7) | |
C3 | −0.0597 (4) | 0.21300 (17) | 0.7662 (3) | 0.0718 (9) | |
C4 | −0.0672 (3) | 0.23323 (13) | 0.3895 (2) | 0.0608 (8) | |
H4A | −0.0293 | 0.2664 | 0.3434 | 0.073* | |
H4B | −0.1634 | 0.2435 | 0.3873 | 0.073* | |
C5 | −0.0515 (3) | 0.16141 (13) | 0.3453 (2) | 0.0483 (7) | |
C6 | 0.0578 (3) | 0.14440 (14) | 0.2922 (2) | 0.0515 (7) | |
H6 | 0.1202 | 0.1787 | 0.2815 | 0.062* | |
C7 | 0.0783 (2) | 0.07862 (13) | 0.2546 (2) | 0.0474 (6) | |
C8 | −0.0192 (2) | 0.02879 (13) | 0.2704 (2) | 0.0476 (6) | |
C9 | −0.1321 (2) | 0.04329 (13) | 0.3237 (2) | 0.0446 (6) | |
C10 | −0.1450 (3) | 0.11031 (13) | 0.3592 (2) | 0.0482 (7) | |
H10 | −0.2195 | 0.1215 | 0.3938 | 0.058* | |
C11 | 0.2028 (3) | 0.06184 (14) | 0.1965 (2) | 0.0570 (7) | |
C12 | 0.2873 (3) | 0.00331 (19) | 0.2537 (3) | 0.0923 (11) | |
H12A | 0.3631 | −0.0063 | 0.2156 | 0.138* | |
H12B | 0.2317 | −0.0372 | 0.2542 | 0.138* | |
H12C | 0.3202 | 0.0166 | 0.3274 | 0.138* | |
C13 | 0.2963 (4) | 0.12395 (19) | 0.1960 (4) | 0.1218 (17) | |
H13A | 0.3737 | 0.1118 | 0.1613 | 0.183* | |
H13B | 0.3265 | 0.1382 | 0.2696 | 0.183* | |
H13C | 0.2477 | 0.1611 | 0.1566 | 0.183* | |
C14 | 0.1564 (4) | 0.0417 (2) | 0.0775 (3) | 0.1063 (13) | |
H14A | 0.1015 | 0.0780 | 0.0416 | 0.159* | |
H14B | 0.1039 | −0.0001 | 0.0751 | 0.159* | |
H14C | 0.2348 | 0.0344 | 0.0413 | 0.159* | |
C15 | −0.2361 (3) | −0.01282 (14) | 0.3450 (2) | 0.0557 (7) | |
C16 | −0.1650 (3) | −0.06927 (17) | 0.4181 (3) | 0.0861 (10) | |
H16A | −0.1219 | −0.0492 | 0.4851 | 0.129* | |
H16B | −0.0974 | −0.0913 | 0.3815 | 0.129* | |
H16C | −0.2308 | −0.1028 | 0.4338 | 0.129* | |
C17 | −0.3064 (3) | −0.04357 (19) | 0.2367 (3) | 0.0892 (11) | |
H17A | −0.3756 | −0.0755 | 0.2513 | 0.134* | |
H17B | −0.2402 | −0.0672 | 0.2006 | 0.134* | |
H17C | −0.3472 | −0.0071 | 0.1907 | 0.134* | |
C18 | −0.3487 (3) | 0.01714 (17) | 0.4041 (3) | 0.0787 (10) | |
H18A | −0.3092 | 0.0356 | 0.4733 | 0.118* | |
H18B | −0.4123 | −0.0186 | 0.4153 | 0.118* | |
H18C | −0.3952 | 0.0532 | 0.3606 | 0.118* | |
C19 | 0.1436 (3) | 0.26413 (15) | 0.5199 (3) | 0.0757 (9) | |
H19A | 0.1794 | 0.2602 | 0.4520 | 0.091* | 0.603 (7) |
H19B | 0.1944 | 0.2332 | 0.5708 | 0.091* | 0.603 (7) |
H19C | 0.1898 | 0.2493 | 0.4607 | 0.091* | 0.397 (7) |
H19D | 0.1905 | 0.2457 | 0.5868 | 0.091* | 0.397 (7) |
C20 | 0.1699 (10) | 0.3379 (4) | 0.5625 (7) | 0.089 (3) | 0.603 (7) |
H20A | 0.1435 | 0.3418 | 0.6348 | 0.106* | 0.603 (7) |
H20B | 0.2663 | 0.3484 | 0.5678 | 0.106* | 0.603 (7) |
C21 | 0.0893 (8) | 0.3884 (3) | 0.4865 (6) | 0.114 (3) | 0.603 (7) |
H21A | 0.1172 | 0.3851 | 0.4155 | 0.171* | 0.603 (7) |
H21B | 0.1053 | 0.4344 | 0.5142 | 0.171* | 0.603 (7) |
H21C | −0.0060 | 0.3779 | 0.4815 | 0.171* | 0.603 (7) |
C20' | 0.1392 (11) | 0.3434 (4) | 0.5241 (13) | 0.080 (4) | 0.397 (7) |
H20C | 0.0926 | 0.3614 | 0.4557 | 0.096* | 0.397 (7) |
H20D | 0.0900 | 0.3583 | 0.5824 | 0.096* | 0.397 (7) |
C21' | 0.2822 (9) | 0.3702 (4) | 0.5435 (8) | 0.099 (4) | 0.397 (7) |
H21D | 0.3345 | 0.3435 | 0.5999 | 0.148* | 0.397 (7) |
H21E | 0.2815 | 0.4177 | 0.5657 | 0.148* | 0.397 (7) |
H21F | 0.3223 | 0.3666 | 0.4775 | 0.148* | 0.397 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0729 (6) | 0.0918 (6) | 0.0841 (6) | −0.0152 (4) | 0.0278 (4) | 0.0025 (5) |
Cl2 | 0.1245 (9) | 0.1910 (13) | 0.0628 (6) | −0.0163 (8) | −0.0066 (6) | −0.0089 (7) |
N1 | 0.0608 (15) | 0.0492 (13) | 0.0552 (14) | 0.0001 (11) | 0.0181 (12) | −0.0011 (11) |
N2 | 0.088 (2) | 0.0758 (18) | 0.0521 (16) | −0.0078 (15) | 0.0189 (14) | 0.0010 (13) |
N3 | 0.0678 (16) | 0.0675 (17) | 0.0648 (17) | 0.0009 (13) | 0.0133 (14) | −0.0104 (14) |
N4 | 0.0683 (15) | 0.0499 (13) | 0.0590 (15) | −0.0065 (12) | 0.0250 (12) | −0.0075 (12) |
O1 | 0.0708 (13) | 0.0429 (11) | 0.1101 (17) | −0.0066 (9) | 0.0286 (12) | −0.0183 (11) |
C1 | 0.0635 (19) | 0.0404 (15) | 0.0607 (19) | 0.0021 (13) | 0.0205 (16) | −0.0062 (14) |
C2 | 0.0700 (19) | 0.0459 (16) | 0.0600 (19) | −0.0018 (14) | 0.0229 (16) | −0.0013 (14) |
C3 | 0.082 (2) | 0.074 (2) | 0.060 (2) | −0.0009 (18) | 0.0095 (18) | −0.0053 (17) |
C4 | 0.077 (2) | 0.0482 (17) | 0.0627 (19) | 0.0037 (14) | 0.0300 (16) | 0.0063 (14) |
C5 | 0.0553 (16) | 0.0444 (15) | 0.0471 (15) | 0.0025 (13) | 0.0135 (13) | 0.0019 (12) |
C6 | 0.0557 (16) | 0.0454 (16) | 0.0569 (17) | −0.0042 (13) | 0.0201 (13) | 0.0019 (13) |
C7 | 0.0436 (15) | 0.0479 (16) | 0.0519 (16) | 0.0023 (12) | 0.0110 (12) | −0.0001 (13) |
C8 | 0.0454 (15) | 0.0426 (15) | 0.0544 (16) | −0.0011 (12) | 0.0054 (13) | −0.0036 (13) |
C9 | 0.0405 (14) | 0.0477 (15) | 0.0450 (15) | −0.0019 (12) | 0.0032 (12) | 0.0017 (12) |
C10 | 0.0444 (15) | 0.0572 (17) | 0.0445 (15) | 0.0021 (13) | 0.0109 (12) | 0.0019 (13) |
C11 | 0.0529 (16) | 0.0536 (17) | 0.068 (2) | −0.0009 (14) | 0.0205 (14) | −0.0032 (15) |
C12 | 0.056 (2) | 0.095 (3) | 0.127 (3) | 0.0140 (19) | 0.015 (2) | 0.009 (2) |
C13 | 0.107 (3) | 0.082 (3) | 0.201 (5) | −0.024 (2) | 0.107 (3) | −0.029 (3) |
C14 | 0.107 (3) | 0.141 (4) | 0.077 (3) | 0.017 (3) | 0.032 (2) | −0.014 (2) |
C15 | 0.0489 (16) | 0.0584 (17) | 0.0601 (18) | −0.0121 (13) | 0.0082 (14) | −0.0007 (15) |
C16 | 0.087 (2) | 0.069 (2) | 0.104 (3) | −0.0099 (18) | 0.017 (2) | 0.025 (2) |
C17 | 0.074 (2) | 0.114 (3) | 0.080 (2) | −0.043 (2) | 0.0121 (18) | −0.022 (2) |
C18 | 0.0605 (19) | 0.086 (2) | 0.095 (2) | −0.0223 (17) | 0.0302 (18) | −0.003 (2) |
C19 | 0.071 (2) | 0.069 (2) | 0.094 (2) | −0.0111 (17) | 0.0353 (18) | −0.0155 (19) |
C20 | 0.088 (6) | 0.094 (5) | 0.085 (6) | −0.035 (4) | 0.017 (5) | −0.016 (4) |
C21 | 0.151 (6) | 0.081 (5) | 0.113 (5) | −0.024 (4) | 0.028 (5) | 0.001 (4) |
C20' | 0.062 (6) | 0.077 (7) | 0.093 (9) | −0.001 (5) | −0.013 (5) | 0.009 (6) |
C21' | 0.101 (7) | 0.100 (6) | 0.099 (6) | −0.036 (5) | 0.025 (5) | −0.007 (5) |
Cl1—C2 | 1.726 (3) | C13—H13C | 0.9600 |
Cl2—C3 | 1.722 (3) | C14—H14A | 0.9600 |
N1—C2 | 1.307 (3) | C14—H14B | 0.9600 |
N1—C1 | 1.356 (3) | C14—H14C | 0.9600 |
N2—C2 | 1.328 (4) | C15—C16 | 1.528 (4) |
N2—C3 | 1.336 (4) | C15—C18 | 1.532 (4) |
N3—C3 | 1.296 (4) | C15—C17 | 1.542 (4) |
N3—C1 | 1.364 (4) | C16—H16A | 0.9600 |
N4—C1 | 1.326 (3) | C16—H16B | 0.9600 |
N4—C19 | 1.466 (4) | C16—H16C | 0.9600 |
N4—C4 | 1.480 (4) | C17—H17A | 0.9600 |
O1—C8 | 1.373 (3) | C17—H17B | 0.9600 |
O1—H1 | 1.0190 | C17—H17C | 0.9600 |
C4—C5 | 1.512 (4) | C18—H18A | 0.9600 |
C4—H4A | 0.9700 | C18—H18B | 0.9600 |
C4—H4B | 0.9700 | C18—H18C | 0.9600 |
C5—C6 | 1.383 (3) | C19—C20 | 1.533 (7) |
C5—C10 | 1.383 (3) | C19—C20' | 1.538 (8) |
C6—C7 | 1.382 (3) | C19—H19A | 0.9600 |
C6—H6 | 0.9300 | C19—H19B | 0.9599 |
C7—C8 | 1.399 (3) | C19—H19C | 0.9600 |
C7—C11 | 1.547 (3) | C19—H19D | 0.9600 |
C8—C9 | 1.405 (3) | C20—C21 | 1.508 (8) |
C9—C10 | 1.382 (3) | C20—H20A | 0.9700 |
C9—C15 | 1.546 (3) | C20—H20B | 0.9700 |
C10—H10 | 0.9300 | C21—H21A | 0.9600 |
C11—C13 | 1.519 (4) | C21—H21B | 0.9600 |
C11—C12 | 1.524 (4) | C21—H21C | 0.9600 |
C11—C14 | 1.531 (4) | C20'—C21' | 1.497 (9) |
C12—H12A | 0.9600 | C20'—H20C | 0.9700 |
C12—H12B | 0.9600 | C20'—H20D | 0.9700 |
C12—H12C | 0.9600 | C21'—H21D | 0.9600 |
C13—H13A | 0.9600 | C21'—H21E | 0.9600 |
C13—H13B | 0.9600 | C21'—H21F | 0.9600 |
C2—N1—C1 | 113.8 (2) | C16—C15—C18 | 107.2 (3) |
C2—N2—C3 | 110.1 (2) | C16—C15—C17 | 110.7 (3) |
C3—N3—C1 | 113.6 (3) | C18—C15—C17 | 106.9 (2) |
C1—N4—C19 | 120.8 (3) | C16—C15—C9 | 109.9 (2) |
C1—N4—C4 | 121.1 (2) | C18—C15—C9 | 111.3 (2) |
C19—N4—C4 | 118.1 (2) | C17—C15—C9 | 110.8 (2) |
C8—O1—H1 | 140.5 | C15—C16—H16A | 109.5 |
N4—C1—N1 | 118.9 (3) | C15—C16—H16B | 109.5 |
N4—C1—N3 | 117.8 (3) | H16A—C16—H16B | 109.5 |
N1—C1—N3 | 123.3 (2) | C15—C16—H16C | 109.5 |
N1—C2—N2 | 129.4 (3) | H16A—C16—H16C | 109.5 |
N1—C2—Cl1 | 115.8 (2) | H16B—C16—H16C | 109.5 |
N2—C2—Cl1 | 114.8 (2) | C15—C17—H17A | 109.5 |
N3—C3—N2 | 129.8 (3) | C15—C17—H17B | 109.5 |
N3—C3—Cl2 | 115.7 (3) | H17A—C17—H17B | 109.5 |
N2—C3—Cl2 | 114.5 (3) | C15—C17—H17C | 109.5 |
N4—C4—C5 | 112.1 (2) | H17A—C17—H17C | 109.5 |
N4—C4—H4A | 109.2 | H17B—C17—H17C | 109.5 |
C5—C4—H4A | 109.2 | C15—C18—H18A | 109.5 |
N4—C4—H4B | 109.2 | C15—C18—H18B | 109.5 |
C5—C4—H4B | 109.2 | H18A—C18—H18B | 109.5 |
H4A—C4—H4B | 107.9 | C15—C18—H18C | 109.5 |
C6—C5—C10 | 118.1 (2) | H18A—C18—H18C | 109.5 |
C6—C5—C4 | 121.3 (2) | H18B—C18—H18C | 109.5 |
C10—C5—C4 | 120.6 (2) | N4—C19—C20 | 116.8 (4) |
C7—C6—C5 | 122.8 (2) | N4—C19—C20' | 106.4 (5) |
C7—C6—H6 | 118.6 | C20—C19—C20' | 20.2 (6) |
C5—C6—H6 | 118.6 | N4—C19—H19A | 108.4 |
C6—C7—C8 | 116.9 (2) | C20—C19—H19A | 108.1 |
C6—C7—C11 | 121.0 (2) | C20'—C19—H19A | 97.2 |
C8—C7—C11 | 122.1 (2) | N4—C19—H19B | 107.7 |
O1—C8—C7 | 119.2 (2) | C20—C19—H19B | 107.9 |
O1—C8—C9 | 118.1 (2) | C20'—C19—H19B | 128.1 |
C7—C8—C9 | 122.6 (2) | H19A—C19—H19B | 107.5 |
C10—C9—C8 | 116.9 (2) | N4—C19—H19C | 110.5 |
C10—C9—C15 | 120.9 (2) | C20—C19—H19C | 117.7 |
C8—C9—C15 | 122.3 (2) | C20'—C19—H19C | 110.0 |
C9—C10—C5 | 122.7 (2) | H19A—C19—H19C | 15.0 |
C9—C10—H10 | 118.7 | H19B—C19—H19C | 93.0 |
C5—C10—H10 | 118.7 | N4—C19—H19D | 110.3 |
C13—C11—C12 | 107.2 (3) | C20—C19—H19D | 90.6 |
C13—C11—C14 | 107.4 (3) | C20'—C19—H19D | 110.8 |
C12—C11—C14 | 109.2 (3) | H19A—C19—H19D | 122.2 |
C13—C11—C7 | 111.2 (2) | H19B—C19—H19D | 19.2 |
C12—C11—C7 | 111.3 (2) | H19C—C19—H19D | 108.8 |
C14—C11—C7 | 110.4 (2) | C21—C20—C19 | 109.9 (6) |
C11—C12—H12A | 109.5 | C21—C20—H20A | 109.7 |
C11—C12—H12B | 109.5 | C19—C20—H20A | 109.7 |
H12A—C12—H12B | 109.5 | C21—C20—H20B | 109.7 |
C11—C12—H12C | 109.5 | C19—C20—H20B | 109.7 |
H12A—C12—H12C | 109.5 | H20A—C20—H20B | 108.2 |
H12B—C12—H12C | 109.5 | C21'—C20'—C19 | 108.7 (7) |
C11—C13—H13A | 109.5 | C21'—C20'—H20C | 109.9 |
C11—C13—H13B | 109.5 | C19—C20'—H20C | 109.9 |
H13A—C13—H13B | 109.5 | C21'—C20'—H20D | 109.9 |
C11—C13—H13C | 109.5 | C19—C20'—H20D | 109.9 |
H13A—C13—H13C | 109.5 | H20C—C20'—H20D | 108.3 |
H13B—C13—H13C | 109.5 | C20'—C21'—H21D | 109.5 |
C11—C14—H14A | 109.5 | C20'—C21'—H21E | 109.5 |
C11—C14—H14B | 109.5 | H21D—C21'—H21E | 109.5 |
H14A—C14—H14B | 109.5 | C20'—C21'—H21F | 109.5 |
C11—C14—H14C | 109.5 | H21D—C21'—H21F | 109.5 |
H14A—C14—H14C | 109.5 | H21E—C21'—H21F | 109.5 |
H14B—C14—H14C | 109.5 | ||
C19—N4—C1—N1 | 178.9 (2) | O1—C8—C9—C10 | −179.4 (2) |
C4—N4—C1—N1 | −3.4 (4) | C7—C8—C9—C10 | 1.0 (4) |
C19—N4—C1—N3 | −1.0 (4) | O1—C8—C9—C15 | 2.1 (4) |
C4—N4—C1—N3 | 176.7 (2) | C7—C8—C9—C15 | −177.4 (2) |
C2—N1—C1—N4 | −178.9 (2) | C8—C9—C10—C5 | −0.9 (4) |
C2—N1—C1—N3 | 1.0 (4) | C15—C9—C10—C5 | 177.6 (2) |
C3—N3—C1—N4 | 179.2 (3) | C6—C5—C10—C9 | 1.0 (4) |
C3—N3—C1—N1 | −0.7 (4) | C4—C5—C10—C9 | −177.5 (2) |
C1—N1—C2—N2 | −0.8 (4) | C6—C7—C11—C13 | 4.0 (4) |
C1—N1—C2—Cl1 | 177.98 (18) | C8—C7—C11—C13 | −176.8 (3) |
C3—N2—C2—N1 | 0.2 (4) | C6—C7—C11—C12 | 123.4 (3) |
C3—N2—C2—Cl1 | −178.5 (2) | C8—C7—C11—C12 | −57.4 (3) |
C1—N3—C3—N2 | 0.1 (5) | C6—C7—C11—C14 | −115.2 (3) |
C1—N3—C3—Cl2 | −179.1 (2) | C8—C7—C11—C14 | 64.0 (3) |
C2—N2—C3—N3 | 0.2 (5) | C10—C9—C15—C16 | −116.9 (3) |
C2—N2—C3—Cl2 | 179.3 (2) | C8—C9—C15—C16 | 61.5 (3) |
C1—N4—C4—C5 | −86.7 (3) | C10—C9—C15—C18 | 1.7 (3) |
C19—N4—C4—C5 | 91.0 (3) | C8—C9—C15—C18 | −179.9 (2) |
N4—C4—C5—C6 | −89.3 (3) | C10—C9—C15—C17 | 120.4 (3) |
N4—C4—C5—C10 | 89.1 (3) | C8—C9—C15—C17 | −61.1 (3) |
C10—C5—C6—C7 | −1.1 (4) | C1—N4—C19—C20 | −74.6 (5) |
C4—C5—C6—C7 | 177.3 (2) | C4—N4—C19—C20 | 107.7 (5) |
C5—C6—C7—C8 | 1.2 (4) | C1—N4—C19—C20' | −93.3 (7) |
C5—C6—C7—C11 | −179.5 (2) | C4—N4—C19—C20' | 88.9 (7) |
C6—C7—C8—O1 | 179.2 (2) | N4—C19—C20—C21 | −57.1 (8) |
C11—C7—C8—O1 | 0.0 (4) | C20'—C19—C20—C21 | 6 (2) |
C6—C7—C8—C9 | −1.2 (4) | N4—C19—C20'—C21' | 178.8 (8) |
C11—C7—C8—C9 | 179.6 (2) | C20—C19—C20'—C21' | 54.8 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O1 | 0.96 | 2.32 | 2.974 (4) | 125 |
C14—H14B···O1 | 0.96 | 2.47 | 3.077 (4) | 121 |
C16—H16B···O1 | 0.96 | 2.40 | 3.026 (4) | 122 |
C17—H17B···O1 | 0.96 | 2.39 | 3.001 (4) | 121 |