








Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618004072/cu3126sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126Isup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IIsup3.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IIIsup4.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IVsup5.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126Vsup6.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIsup7.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIIsup8.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIIIsup9.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IXsup10.hkl |
CCDC references: 1828709; 1828708; 1828707; 1828706; 1828705; 1828704; 1828703; 1828702; 1828701
For all structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POV-RAY for Windows (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009).
C14H19N4O3+·C5HCl2O2S− | F(000) = 1008 |
Mr = 487.35 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0030 (3) Å | Cell parameters from 3912 reflections |
b = 28.2985 (15) Å | θ = 3.3–28.2° |
c = 11.5070 (6) Å | µ = 0.43 mm−1 |
β = 106.080 (5)° | T = 293 K |
V = 2191.2 (2) Å3 | Prism, colorless |
Z = 4 | 0.35 × 0.35 × 0.15 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 5013 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3721 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −34→36 |
Tmin = 0.849, Tmax = 1.000 | l = −14→14 |
13413 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0502P)2 + 1.4433P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5013 reflections | Δρmax = 0.48 e Å−3 |
283 parameters | Δρmin = −0.55 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.77270 (12) | 0.42686 (3) | 0.43950 (6) | 0.0599 (2) | |
Cl1 | −0.87433 (10) | 0.47078 (3) | 0.64505 (7) | 0.0599 (2) | |
Cl2 | −0.47824 (19) | 0.38802 (5) | 0.32300 (9) | 0.1047 (4) | |
O1 | −0.2060 (2) | 0.48057 (7) | 0.76195 (18) | 0.0544 (5) | |
O2 | −0.4667 (3) | 0.47108 (9) | 0.83233 (17) | 0.0655 (6) | |
C17 | −0.6950 (4) | 0.45035 (9) | 0.5825 (2) | 0.0421 (5) | |
C18 | −0.4946 (3) | 0.44966 (9) | 0.6300 (2) | 0.0388 (5) | |
C19 | −0.3997 (4) | 0.42921 (10) | 0.5475 (3) | 0.0529 (7) | |
H19 | −0.2628 | 0.4259 | 0.5633 | 0.064* | |
C20 | −0.5310 (5) | 0.41526 (11) | 0.4441 (3) | 0.0606 (8) | |
C21 | −0.3814 (3) | 0.46845 (9) | 0.7515 (2) | 0.0409 (5) | |
O10 | −0.0432 (2) | 0.75213 (6) | 0.68018 (16) | 0.0502 (5) | |
O11 | 0.2681 (3) | 0.81054 (6) | 0.71423 (14) | 0.0421 (4) | |
O12 | 0.6186 (2) | 0.78919 (7) | 0.86405 (17) | 0.0542 (5) | |
N1 | −0.0492 (3) | 0.54897 (7) | 0.91313 (17) | 0.0360 (4) | |
H1 | −0.0967 | 0.5253 | 0.8675 | 0.043* | |
N2 | −0.2930 (3) | 0.53963 (7) | 1.0089 (2) | 0.0444 (5) | |
H2B | −0.3535 | 0.5483 | 1.0610 | 0.053* | |
H2A | −0.3336 | 0.5153 | 0.9643 | 0.053* | |
N3 | −0.0740 (3) | 0.60158 (7) | 1.06647 (18) | 0.0390 (4) | |
N4 | 0.1497 (3) | 0.66085 (8) | 1.1260 (2) | 0.0554 (6) | |
H4A | 0.0861 | 0.6694 | 1.1767 | 0.066* | |
H4B | 0.2532 | 0.6763 | 1.1216 | 0.066* | |
C2 | −0.1372 (3) | 0.56383 (8) | 0.9975 (2) | 0.0343 (5) | |
C4 | 0.0878 (3) | 0.62380 (8) | 1.0545 (2) | 0.0367 (5) | |
C5 | 0.1915 (3) | 0.60932 (8) | 0.96918 (19) | 0.0322 (5) | |
C6 | 0.1147 (3) | 0.57175 (8) | 0.9010 (2) | 0.0340 (5) | |
H6 | 0.1756 | 0.5610 | 0.8438 | 0.041* | |
C7 | 0.3745 (3) | 0.63392 (8) | 0.9574 (2) | 0.0355 (5) | |
H7A | 0.4413 | 0.6134 | 0.9137 | 0.043* | |
H7B | 0.4635 | 0.6385 | 1.0378 | 0.043* | |
C8 | 0.3403 (3) | 0.68138 (8) | 0.89392 (19) | 0.0309 (4) | |
C9 | 0.1579 (3) | 0.69336 (8) | 0.8156 (2) | 0.0343 (5) | |
H9 | 0.0521 | 0.6723 | 0.8024 | 0.041* | |
C10 | 0.1324 (3) | 0.73671 (8) | 0.75648 (19) | 0.0339 (5) | |
C11 | 0.2899 (3) | 0.76820 (8) | 0.77539 (19) | 0.0333 (5) | |
C12 | 0.4738 (3) | 0.75578 (8) | 0.8538 (2) | 0.0364 (5) | |
C13 | 0.4983 (3) | 0.71272 (8) | 0.9128 (2) | 0.0359 (5) | |
H13 | 0.6209 | 0.7047 | 0.9652 | 0.043* | |
C14 | −0.1936 (4) | 0.71795 (12) | 0.6364 (3) | 0.0732 (10) | |
H14A | −0.2978 | 0.7315 | 0.5725 | 0.110* | |
H14B | −0.2468 | 0.7081 | 0.7009 | 0.110* | |
H14C | −0.1383 | 0.6912 | 0.6060 | 0.110* | |
C15 | 0.2321 (5) | 0.84958 (10) | 0.7838 (3) | 0.0545 (7) | |
H15A | 0.1110 | 0.8443 | 0.8056 | 0.082* | |
H15B | 0.2205 | 0.8780 | 0.7368 | 0.082* | |
H15C | 0.3405 | 0.8526 | 0.8558 | 0.082* | |
C16 | 0.8042 (4) | 0.78110 (12) | 0.9510 (3) | 0.0655 (9) | |
H16A | 0.8613 | 0.7523 | 0.9318 | 0.098* | |
H16B | 0.7842 | 0.7786 | 1.0300 | 0.098* | |
H16C | 0.8923 | 0.8070 | 0.9498 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0698 (5) | 0.0656 (5) | 0.0391 (4) | −0.0036 (4) | 0.0063 (3) | −0.0038 (3) |
Cl1 | 0.0461 (4) | 0.0705 (5) | 0.0631 (4) | 0.0135 (3) | 0.0152 (3) | −0.0055 (4) |
Cl2 | 0.1467 (10) | 0.1179 (9) | 0.0704 (6) | −0.0195 (7) | 0.0649 (6) | −0.0407 (6) |
O1 | 0.0421 (9) | 0.0632 (13) | 0.0633 (12) | −0.0120 (9) | 0.0238 (9) | −0.0240 (10) |
O2 | 0.0560 (11) | 0.1049 (18) | 0.0432 (10) | −0.0314 (11) | 0.0266 (9) | −0.0203 (11) |
C17 | 0.0494 (13) | 0.0397 (13) | 0.0376 (12) | −0.0004 (11) | 0.0125 (10) | −0.0002 (10) |
C18 | 0.0441 (12) | 0.0374 (13) | 0.0393 (12) | −0.0064 (10) | 0.0189 (10) | −0.0027 (10) |
C19 | 0.0557 (15) | 0.0575 (17) | 0.0550 (16) | −0.0102 (13) | 0.0309 (13) | −0.0114 (13) |
C20 | 0.090 (2) | 0.0573 (18) | 0.0443 (15) | −0.0095 (16) | 0.0344 (15) | −0.0124 (13) |
C21 | 0.0418 (12) | 0.0416 (13) | 0.0428 (13) | −0.0061 (10) | 0.0172 (10) | −0.0038 (11) |
O10 | 0.0382 (9) | 0.0419 (10) | 0.0576 (11) | −0.0025 (7) | −0.0080 (8) | 0.0113 (8) |
O11 | 0.0574 (10) | 0.0323 (9) | 0.0355 (8) | −0.0055 (8) | 0.0109 (7) | 0.0052 (7) |
O12 | 0.0411 (9) | 0.0534 (11) | 0.0606 (11) | −0.0197 (8) | 0.0017 (8) | 0.0149 (9) |
N1 | 0.0414 (10) | 0.0309 (10) | 0.0395 (10) | −0.0032 (8) | 0.0177 (8) | −0.0046 (8) |
N2 | 0.0481 (11) | 0.0377 (11) | 0.0569 (13) | −0.0061 (9) | 0.0302 (10) | −0.0058 (10) |
N3 | 0.0488 (11) | 0.0298 (10) | 0.0457 (11) | −0.0015 (8) | 0.0252 (9) | −0.0036 (8) |
N4 | 0.0684 (15) | 0.0432 (13) | 0.0661 (15) | −0.0170 (11) | 0.0380 (12) | −0.0222 (11) |
C2 | 0.0397 (11) | 0.0278 (11) | 0.0390 (12) | 0.0044 (9) | 0.0167 (9) | 0.0051 (9) |
C4 | 0.0450 (12) | 0.0283 (11) | 0.0398 (12) | 0.0017 (9) | 0.0166 (10) | 0.0009 (9) |
C5 | 0.0367 (11) | 0.0277 (11) | 0.0344 (11) | 0.0034 (9) | 0.0133 (9) | 0.0050 (9) |
C6 | 0.0391 (11) | 0.0317 (12) | 0.0359 (11) | 0.0040 (9) | 0.0182 (9) | 0.0028 (9) |
C7 | 0.0350 (11) | 0.0315 (12) | 0.0409 (12) | 0.0027 (9) | 0.0119 (9) | 0.0042 (10) |
C8 | 0.0326 (10) | 0.0299 (11) | 0.0317 (11) | 0.0009 (8) | 0.0118 (9) | 0.0017 (9) |
C9 | 0.0305 (10) | 0.0314 (11) | 0.0398 (12) | −0.0039 (9) | 0.0081 (9) | 0.0007 (9) |
C10 | 0.0315 (10) | 0.0353 (12) | 0.0319 (11) | 0.0006 (9) | 0.0040 (9) | 0.0011 (9) |
C11 | 0.0412 (11) | 0.0291 (11) | 0.0296 (10) | −0.0035 (9) | 0.0101 (9) | 0.0035 (9) |
C12 | 0.0338 (11) | 0.0384 (13) | 0.0365 (11) | −0.0090 (9) | 0.0090 (9) | 0.0023 (10) |
C13 | 0.0297 (10) | 0.0408 (13) | 0.0360 (11) | −0.0022 (9) | 0.0069 (9) | 0.0046 (10) |
C14 | 0.0490 (16) | 0.0556 (19) | 0.090 (2) | −0.0094 (14) | −0.0229 (16) | 0.0095 (17) |
C15 | 0.0746 (18) | 0.0369 (14) | 0.0536 (16) | 0.0044 (13) | 0.0207 (14) | 0.0019 (12) |
C16 | 0.0421 (14) | 0.077 (2) | 0.0668 (19) | −0.0266 (14) | −0.0026 (13) | 0.0100 (16) |
S1—C20 | 1.711 (3) | N4—H4A | 0.8600 |
S1—C17 | 1.717 (3) | N4—H4B | 0.8600 |
Cl1—C17 | 1.712 (3) | C4—C5 | 1.433 (3) |
Cl2—C20 | 1.720 (3) | C5—C6 | 1.342 (3) |
O1—C21 | 1.249 (3) | C5—C7 | 1.497 (3) |
O2—C21 | 1.239 (3) | C6—H6 | 0.9300 |
C17—C18 | 1.357 (3) | C7—C8 | 1.516 (3) |
C18—C19 | 1.424 (3) | C7—H7A | 0.9700 |
C18—C21 | 1.501 (3) | C7—H7B | 0.9700 |
C19—C20 | 1.346 (4) | C8—C9 | 1.386 (3) |
C19—H19 | 0.9300 | C8—C13 | 1.388 (3) |
O10—C10 | 1.369 (3) | C9—C10 | 1.390 (3) |
O10—C14 | 1.416 (3) | C9—H9 | 0.9300 |
O11—C11 | 1.377 (3) | C10—C11 | 1.388 (3) |
O11—C15 | 1.427 (3) | C11—C12 | 1.397 (3) |
O12—C12 | 1.367 (3) | C12—C13 | 1.382 (3) |
O12—C16 | 1.422 (3) | C13—H13 | 0.9300 |
N1—C2 | 1.353 (3) | C14—H14A | 0.9600 |
N1—C6 | 1.356 (3) | C14—H14B | 0.9600 |
N1—H1 | 0.8600 | C14—H14C | 0.9600 |
N2—C2 | 1.325 (3) | C15—H15A | 0.9600 |
N2—H2B | 0.8600 | C15—H15B | 0.9600 |
N2—H2A | 0.8600 | C15—H15C | 0.9600 |
N3—C2 | 1.331 (3) | C16—H16A | 0.9600 |
N3—C4 | 1.336 (3) | C16—H16B | 0.9600 |
N4—C4 | 1.329 (3) | C16—H16C | 0.9600 |
C20—S1—C17 | 89.79 (13) | C5—C7—H7A | 108.4 |
C18—C17—Cl1 | 129.22 (19) | C8—C7—H7A | 108.4 |
C18—C17—S1 | 113.47 (18) | C5—C7—H7B | 108.4 |
Cl1—C17—S1 | 117.31 (15) | C8—C7—H7B | 108.4 |
C17—C18—C19 | 111.0 (2) | H7A—C7—H7B | 107.5 |
C17—C18—C21 | 126.2 (2) | C9—C8—C13 | 119.8 (2) |
C19—C18—C21 | 122.8 (2) | C9—C8—C7 | 121.65 (19) |
C20—C19—C18 | 112.2 (3) | C13—C8—C7 | 118.56 (19) |
C20—C19—H19 | 123.9 | C8—C9—C10 | 120.3 (2) |
C18—C19—H19 | 123.9 | C8—C9—H9 | 119.8 |
C19—C20—S1 | 113.5 (2) | C10—C9—H9 | 119.8 |
C19—C20—Cl2 | 126.9 (3) | O10—C10—C11 | 115.45 (19) |
S1—C20—Cl2 | 119.59 (19) | O10—C10—C9 | 124.5 (2) |
O2—C21—O1 | 125.3 (2) | C11—C10—C9 | 120.07 (19) |
O2—C21—C18 | 118.7 (2) | O11—C11—C10 | 120.51 (19) |
O1—C21—C18 | 116.0 (2) | O11—C11—C12 | 120.08 (19) |
C10—O10—C14 | 117.3 (2) | C10—C11—C12 | 119.4 (2) |
C11—O11—C15 | 113.52 (18) | O12—C12—C13 | 125.4 (2) |
C12—O12—C16 | 117.4 (2) | O12—C12—C11 | 114.2 (2) |
C2—N1—C6 | 119.49 (19) | C13—C12—C11 | 120.4 (2) |
C2—N1—H1 | 120.3 | C12—C13—C8 | 120.1 (2) |
C6—N1—H1 | 120.3 | C12—C13—H13 | 119.9 |
C2—N2—H2B | 120.0 | C8—C13—H13 | 119.9 |
C2—N2—H2A | 120.0 | O10—C14—H14A | 109.5 |
H2B—N2—H2A | 120.0 | O10—C14—H14B | 109.5 |
C2—N3—C4 | 117.89 (19) | H14A—C14—H14B | 109.5 |
C4—N4—H4A | 120.0 | O10—C14—H14C | 109.5 |
C4—N4—H4B | 120.0 | H14A—C14—H14C | 109.5 |
H4A—N4—H4B | 120.0 | H14B—C14—H14C | 109.5 |
N2—C2—N3 | 120.1 (2) | O11—C15—H15A | 109.5 |
N2—C2—N1 | 117.5 (2) | O11—C15—H15B | 109.5 |
N3—C2—N1 | 122.3 (2) | H15A—C15—H15B | 109.5 |
N4—C4—N3 | 116.6 (2) | O11—C15—H15C | 109.5 |
N4—C4—C5 | 120.6 (2) | H15A—C15—H15C | 109.5 |
N3—C4—C5 | 122.7 (2) | H15B—C15—H15C | 109.5 |
C6—C5—C4 | 115.43 (19) | O12—C16—H16A | 109.5 |
C6—C5—C7 | 122.03 (19) | O12—C16—H16B | 109.5 |
C4—C5—C7 | 122.5 (2) | H16A—C16—H16B | 109.5 |
C5—C6—N1 | 122.04 (19) | O12—C16—H16C | 109.5 |
C5—C6—H6 | 119.0 | H16A—C16—H16C | 109.5 |
N1—C6—H6 | 119.0 | H16B—C16—H16C | 109.5 |
C5—C7—C8 | 115.49 (18) | ||
C20—S1—C17—C18 | 0.6 (2) | C2—N1—C6—C5 | −1.0 (3) |
C20—S1—C17—Cl1 | −179.16 (18) | C6—C5—C7—C8 | 105.8 (2) |
Cl1—C17—C18—C19 | 179.6 (2) | C4—C5—C7—C8 | −75.0 (3) |
S1—C17—C18—C19 | −0.1 (3) | C5—C7—C8—C9 | −22.3 (3) |
Cl1—C17—C18—C21 | −1.6 (4) | C5—C7—C8—C13 | 159.6 (2) |
S1—C17—C18—C21 | 178.6 (2) | C13—C8—C9—C10 | −0.4 (3) |
C17—C18—C19—C20 | −0.7 (4) | C7—C8—C9—C10 | −178.5 (2) |
C21—C18—C19—C20 | −179.4 (3) | C14—O10—C10—C11 | 165.9 (2) |
C18—C19—C20—S1 | 1.1 (4) | C14—O10—C10—C9 | −15.7 (4) |
C18—C19—C20—Cl2 | −178.7 (2) | C8—C9—C10—O10 | −178.2 (2) |
C17—S1—C20—C19 | −1.0 (3) | C8—C9—C10—C11 | 0.2 (3) |
C17—S1—C20—Cl2 | 178.8 (2) | C15—O11—C11—C10 | 99.2 (3) |
C17—C18—C21—O2 | 25.0 (4) | C15—O11—C11—C12 | −83.2 (3) |
C19—C18—C21—O2 | −156.4 (3) | O10—C10—C11—O11 | −3.7 (3) |
C17—C18—C21—O1 | −154.6 (3) | C9—C10—C11—O11 | 177.8 (2) |
C19—C18—C21—O1 | 24.0 (4) | O10—C10—C11—C12 | 178.8 (2) |
C4—N3—C2—N2 | 177.7 (2) | C9—C10—C11—C12 | 0.2 (3) |
C4—N3—C2—N1 | −3.1 (3) | C16—O12—C12—C13 | −6.4 (4) |
C6—N1—C2—N2 | −177.8 (2) | C16—O12—C12—C11 | 174.1 (2) |
C6—N1—C2—N3 | 2.9 (3) | O11—C11—C12—O12 | 1.5 (3) |
C2—N3—C4—N4 | −178.8 (2) | C10—C11—C12—O12 | 179.1 (2) |
C2—N3—C4—C5 | 1.5 (3) | O11—C11—C12—C13 | −178.1 (2) |
N4—C4—C5—C6 | −179.4 (2) | C10—C11—C12—C13 | −0.5 (3) |
N3—C4—C5—C6 | 0.2 (3) | O12—C12—C13—C8 | −179.2 (2) |
N4—C4—C5—C7 | 1.3 (3) | C11—C12—C13—C8 | 0.3 (3) |
N3—C4—C5—C7 | −179.1 (2) | C9—C8—C13—C12 | 0.1 (3) |
C4—C5—C6—N1 | −0.4 (3) | C7—C8—C13—C12 | 178.3 (2) |
C7—C5—C6—N1 | 178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.77 | 2.631 (3) | 174 |
N2—H2A···O2 | 0.86 | 1.99 | 2.829 (3) | 166 |
N2—H2B···O2i | 0.86 | 2.06 | 2.822 (3) | 147 |
N4—H4A···O11ii | 0.86 | 2.45 | 3.214 (3) | 148 |
N4—H4A···O12ii | 0.86 | 2.41 | 3.143 (3) | 144 |
N4—H4B···O10iii | 0.86 | 2.46 | 3.215 (3) | 147 |
C7—H7A···Cl2iv | 0.97 | 2.81 | 3.553 (2) | 134 |
Symmetry codes: (i) −x−1, −y+1, −z+2; (ii) x−1/2, −y+3/2, z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x, −y+1, −z+1. |
C14H19N4O3+·C5H2BrO2S−·H2O | F(000) = 1056 |
Mr = 515.38 | Dx = 1.578 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.9440 (8) Å | Cell parameters from 4168 reflections |
b = 6.8991 (3) Å | θ = 3.3–28.5° |
c = 19.7206 (14) Å | µ = 2.04 mm−1 |
β = 109.773 (7)° | T = 293 K |
V = 2169.4 (2) Å3 | Prism, colorless |
Z = 4 | 0.60 × 0.50 × 0.40 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 4949 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3766 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω scans | h = −22→21 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −8→8 |
Tmin = 0.615, Tmax = 1.000 | l = −16→25 |
12646 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0414P)2 + 1.5827P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4949 reflections | Δρmax = 0.95 e Å−3 |
289 parameters | Δρmin = −1.02 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.27564 (2) | 0.64387 (4) | 0.75131 (2) | 0.04939 (12) | |
S1 | 0.17543 (5) | 0.10256 (12) | 0.63943 (5) | 0.0501 (2) | |
O1 | 0.39515 (12) | 0.3500 (3) | 0.70669 (12) | 0.0442 (5) | |
O2 | 0.34958 (15) | 0.0670 (3) | 0.65662 (15) | 0.0626 (7) | |
C17 | 0.33875 (17) | 0.2275 (4) | 0.68118 (15) | 0.0365 (6) | |
C18 | 0.25209 (17) | 0.2707 (4) | 0.67934 (15) | 0.0347 (6) | |
C19 | 0.21719 (17) | 0.4243 (4) | 0.70302 (15) | 0.0356 (6) | |
C20 | 0.12997 (18) | 0.4063 (5) | 0.68844 (17) | 0.0467 (7) | |
H20 | 0.0974 | 0.4982 | 0.7012 | 0.056* | |
C21 | 0.09992 (19) | 0.2402 (5) | 0.65399 (18) | 0.0543 (8) | |
H21 | 0.0437 | 0.2045 | 0.6397 | 0.065* | |
N1 | 0.51777 (13) | 0.3354 (3) | 0.64391 (12) | 0.0327 (5) | |
H1 | 0.4921 | 0.3069 | 0.6735 | 0.039* | |
N2 | 0.46864 (15) | 0.0544 (3) | 0.58253 (14) | 0.0429 (6) | |
H2B | 0.4645 | −0.0254 | 0.5480 | 0.051* | |
H2A | 0.4431 | 0.0307 | 0.6126 | 0.051* | |
N3 | 0.55390 (12) | 0.2503 (3) | 0.54287 (11) | 0.0291 (5) | |
N4 | 0.62901 (13) | 0.4620 (3) | 0.49985 (12) | 0.0353 (5) | |
H4A | 0.6231 | 0.3836 | 0.4645 | 0.042* | |
H4B | 0.6564 | 0.5684 | 0.5026 | 0.042* | |
O10 | 0.93582 (11) | 0.4983 (3) | 0.67678 (11) | 0.0428 (5) | |
O11 | 0.97913 (11) | 0.8021 (3) | 0.61440 (11) | 0.0408 (5) | |
O12 | 0.86853 (12) | 1.0730 (3) | 0.54712 (12) | 0.0446 (5) | |
C2 | 0.51412 (15) | 0.2129 (4) | 0.58939 (14) | 0.0306 (6) | |
C4 | 0.59590 (14) | 0.4186 (4) | 0.55020 (14) | 0.0273 (5) | |
C5 | 0.60366 (14) | 0.5517 (4) | 0.60779 (14) | 0.0300 (6) | |
C6 | 0.56173 (15) | 0.5030 (4) | 0.65217 (14) | 0.0323 (6) | |
H6 | 0.5629 | 0.5865 | 0.6895 | 0.039* | |
C7 | 0.64434 (15) | 0.7480 (4) | 0.61243 (16) | 0.0343 (6) | |
H7A | 0.6434 | 0.8103 | 0.6563 | 0.041* | |
H7B | 0.6097 | 0.8254 | 0.5723 | 0.041* | |
C8 | 0.73412 (14) | 0.7551 (4) | 0.61201 (14) | 0.0303 (6) | |
C9 | 0.79241 (15) | 0.6155 (4) | 0.64650 (14) | 0.0321 (6) | |
H9 | 0.7770 | 0.5129 | 0.6700 | 0.039* | |
C10 | 0.87406 (15) | 0.6289 (4) | 0.64596 (14) | 0.0314 (6) | |
C11 | 0.89743 (15) | 0.7850 (4) | 0.61214 (14) | 0.0311 (6) | |
C12 | 0.83893 (16) | 0.9250 (4) | 0.57800 (15) | 0.0329 (6) | |
C13 | 0.75675 (16) | 0.9090 (4) | 0.57718 (15) | 0.0349 (6) | |
H13 | 0.7171 | 1.0013 | 0.5533 | 0.042* | |
C14 | 0.91624 (19) | 0.3356 (4) | 0.71257 (17) | 0.0460 (7) | |
H14A | 0.8732 | 0.2599 | 0.6787 | 0.069* | |
H14B | 0.8968 | 0.3797 | 0.7503 | 0.069* | |
H14C | 0.9655 | 0.2575 | 0.7328 | 0.069* | |
C15 | 0.9935 (2) | 0.7293 (6) | 0.5527 (2) | 0.0655 (10) | |
H15A | 0.9575 | 0.7948 | 0.5106 | 0.098* | |
H15B | 0.9817 | 0.5929 | 0.5484 | 0.098* | |
H15C | 1.0510 | 0.7508 | 0.5570 | 0.098* | |
C16 | 0.8101 (2) | 1.2158 (5) | 0.5092 (2) | 0.0568 (9) | |
H16A | 0.7664 | 1.1557 | 0.4705 | 0.085* | |
H16B | 0.8382 | 1.3108 | 0.4899 | 0.085* | |
H16C | 0.7863 | 1.2776 | 0.5414 | 0.085* | |
O1W | 0.38659 (18) | 0.6976 (3) | 0.63400 (14) | 0.0578 (6) | |
H1W | 0.385 (3) | 0.612 (4) | 0.6622 (19) | 0.087* | |
H2W | 0.360 (2) | 0.787 (4) | 0.643 (2) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0514 (2) | 0.03644 (18) | 0.0718 (2) | 0.00199 (13) | 0.03573 (17) | −0.00563 (15) |
S1 | 0.0456 (4) | 0.0508 (5) | 0.0561 (5) | −0.0031 (4) | 0.0203 (4) | −0.0102 (4) |
O1 | 0.0376 (11) | 0.0442 (12) | 0.0605 (14) | 0.0036 (9) | 0.0292 (10) | 0.0022 (10) |
O2 | 0.0639 (15) | 0.0373 (12) | 0.108 (2) | 0.0054 (11) | 0.0578 (14) | −0.0108 (12) |
C17 | 0.0388 (15) | 0.0342 (15) | 0.0456 (17) | 0.0097 (13) | 0.0260 (13) | 0.0092 (13) |
C18 | 0.0369 (14) | 0.0326 (14) | 0.0403 (16) | 0.0063 (12) | 0.0207 (12) | 0.0054 (12) |
C19 | 0.0340 (14) | 0.0376 (15) | 0.0406 (16) | 0.0064 (12) | 0.0195 (12) | 0.0049 (12) |
C20 | 0.0367 (15) | 0.0515 (19) | 0.056 (2) | 0.0122 (14) | 0.0215 (14) | 0.0008 (16) |
C21 | 0.0315 (15) | 0.071 (2) | 0.060 (2) | 0.0022 (16) | 0.0162 (14) | −0.0005 (19) |
N1 | 0.0285 (11) | 0.0417 (13) | 0.0342 (12) | −0.0022 (10) | 0.0189 (9) | −0.0018 (10) |
N2 | 0.0461 (14) | 0.0386 (13) | 0.0562 (16) | −0.0105 (11) | 0.0332 (12) | −0.0071 (12) |
N3 | 0.0264 (10) | 0.0296 (11) | 0.0347 (12) | 0.0013 (9) | 0.0149 (9) | −0.0020 (9) |
N4 | 0.0345 (12) | 0.0374 (13) | 0.0409 (13) | −0.0050 (10) | 0.0217 (10) | −0.0049 (10) |
O10 | 0.0242 (9) | 0.0474 (12) | 0.0571 (13) | 0.0074 (8) | 0.0141 (8) | 0.0171 (10) |
O11 | 0.0229 (9) | 0.0552 (12) | 0.0475 (12) | −0.0037 (8) | 0.0162 (8) | −0.0006 (10) |
O12 | 0.0384 (11) | 0.0377 (11) | 0.0651 (14) | 0.0024 (9) | 0.0272 (10) | 0.0118 (10) |
C2 | 0.0241 (12) | 0.0311 (13) | 0.0381 (15) | 0.0021 (10) | 0.0127 (11) | 0.0016 (12) |
C4 | 0.0185 (11) | 0.0309 (13) | 0.0339 (14) | 0.0045 (10) | 0.0105 (10) | 0.0004 (11) |
C5 | 0.0181 (11) | 0.0341 (14) | 0.0393 (15) | 0.0019 (10) | 0.0117 (10) | −0.0046 (11) |
C6 | 0.0237 (12) | 0.0405 (15) | 0.0337 (14) | 0.0015 (11) | 0.0110 (10) | −0.0083 (12) |
C7 | 0.0236 (12) | 0.0338 (14) | 0.0480 (17) | −0.0003 (11) | 0.0154 (11) | −0.0086 (12) |
C8 | 0.0221 (12) | 0.0317 (14) | 0.0382 (15) | −0.0018 (10) | 0.0117 (11) | −0.0077 (11) |
C9 | 0.0267 (12) | 0.0341 (14) | 0.0368 (15) | −0.0025 (11) | 0.0123 (11) | −0.0005 (11) |
C10 | 0.0226 (11) | 0.0354 (14) | 0.0344 (15) | 0.0005 (11) | 0.0073 (10) | −0.0023 (12) |
C11 | 0.0218 (11) | 0.0385 (14) | 0.0337 (14) | −0.0049 (11) | 0.0102 (10) | −0.0061 (12) |
C12 | 0.0327 (13) | 0.0302 (13) | 0.0384 (15) | −0.0042 (11) | 0.0153 (12) | −0.0033 (12) |
C13 | 0.0264 (12) | 0.0326 (14) | 0.0458 (17) | 0.0041 (11) | 0.0122 (11) | −0.0010 (12) |
C14 | 0.0400 (16) | 0.0497 (18) | 0.0487 (18) | 0.0078 (14) | 0.0156 (14) | 0.0143 (15) |
C15 | 0.0463 (19) | 0.098 (3) | 0.065 (2) | 0.010 (2) | 0.0351 (17) | −0.002 (2) |
C16 | 0.061 (2) | 0.0453 (18) | 0.077 (2) | 0.0116 (16) | 0.0391 (18) | 0.0174 (17) |
O1W | 0.0942 (19) | 0.0384 (13) | 0.0622 (16) | 0.0077 (13) | 0.0543 (14) | 0.0027 (11) |
Br1—C19 | 1.883 (3) | O12—C16 | 1.417 (4) |
S1—C21 | 1.694 (3) | C4—C5 | 1.432 (4) |
S1—C18 | 1.720 (3) | C5—C6 | 1.343 (4) |
O1—C17 | 1.247 (3) | C5—C7 | 1.508 (4) |
O2—C17 | 1.247 (3) | C6—H6 | 0.9300 |
C17—C18 | 1.487 (4) | C7—C8 | 1.525 (3) |
C18—C19 | 1.371 (4) | C7—H7A | 0.9700 |
C19—C20 | 1.412 (4) | C7—H7B | 0.9700 |
C20—C21 | 1.342 (5) | C8—C9 | 1.383 (4) |
C20—H20 | 0.9300 | C8—C13 | 1.387 (4) |
C21—H21 | 0.9300 | C9—C10 | 1.390 (3) |
N1—C2 | 1.353 (3) | C9—H9 | 0.9300 |
N1—C6 | 1.355 (3) | C10—C11 | 1.393 (4) |
N1—H1 | 0.8600 | C11—C12 | 1.385 (4) |
N2—C2 | 1.318 (3) | C12—C13 | 1.391 (4) |
N2—H2B | 0.8600 | C13—H13 | 0.9300 |
N2—H2A | 0.8600 | C14—H14A | 0.9600 |
N3—C2 | 1.334 (3) | C14—H14B | 0.9600 |
N3—C4 | 1.344 (3) | C14—H14C | 0.9600 |
N4—C4 | 1.329 (3) | C15—H15A | 0.9600 |
N4—H4A | 0.8600 | C15—H15B | 0.9600 |
N4—H4B | 0.8600 | C15—H15C | 0.9600 |
O10—C10 | 1.358 (3) | C16—H16A | 0.9600 |
O10—C14 | 1.424 (3) | C16—H16B | 0.9600 |
O11—C11 | 1.375 (3) | C16—H16C | 0.9600 |
O11—C15 | 1.412 (4) | O1W—H1W | 0.816 (10) |
O12—C12 | 1.368 (3) | O1W—H2W | 0.816 (10) |
C21—S1—C18 | 92.37 (15) | C5—C7—H7A | 107.9 |
O2—C17—O1 | 124.4 (2) | C8—C7—H7A | 107.9 |
O2—C17—C18 | 116.3 (3) | C5—C7—H7B | 107.9 |
O1—C17—C18 | 119.3 (2) | C8—C7—H7B | 107.9 |
C19—C18—C17 | 133.1 (3) | H7A—C7—H7B | 107.2 |
C19—C18—S1 | 109.3 (2) | C9—C8—C13 | 120.4 (2) |
C17—C18—S1 | 117.6 (2) | C9—C8—C7 | 121.5 (2) |
C18—C19—C20 | 113.9 (3) | C13—C8—C7 | 118.1 (2) |
C18—C19—Br1 | 125.5 (2) | C8—C9—C10 | 119.8 (2) |
C20—C19—Br1 | 120.6 (2) | C8—C9—H9 | 120.1 |
C21—C20—C19 | 111.7 (3) | C10—C9—H9 | 120.1 |
C21—C20—H20 | 124.1 | O10—C10—C9 | 124.8 (2) |
C19—C20—H20 | 124.1 | O10—C10—C11 | 115.2 (2) |
C20—C21—S1 | 112.7 (2) | C9—C10—C11 | 120.0 (2) |
C20—C21—H21 | 123.7 | O11—C11—C12 | 120.2 (2) |
S1—C21—H21 | 123.7 | O11—C11—C10 | 119.8 (2) |
C2—N1—C6 | 120.3 (2) | C12—C11—C10 | 120.0 (2) |
C2—N1—H1 | 119.9 | O12—C12—C11 | 115.3 (2) |
C6—N1—H1 | 119.9 | O12—C12—C13 | 124.8 (2) |
C2—N2—H2B | 120.0 | C11—C12—C13 | 120.0 (2) |
C2—N2—H2A | 120.0 | C8—C13—C12 | 119.9 (2) |
H2B—N2—H2A | 120.0 | C8—C13—H13 | 120.1 |
C2—N3—C4 | 117.7 (2) | C12—C13—H13 | 120.1 |
C4—N4—H4A | 120.0 | O10—C14—H14A | 109.5 |
C4—N4—H4B | 120.0 | O10—C14—H14B | 109.5 |
H4A—N4—H4B | 120.0 | H14A—C14—H14B | 109.5 |
C10—O10—C14 | 118.1 (2) | O10—C14—H14C | 109.5 |
C11—O11—C15 | 114.0 (2) | H14A—C14—H14C | 109.5 |
C12—O12—C16 | 117.3 (2) | H14B—C14—H14C | 109.5 |
N2—C2—N3 | 120.2 (2) | O11—C15—H15A | 109.5 |
N2—C2—N1 | 117.9 (2) | O11—C15—H15B | 109.5 |
N3—C2—N1 | 121.8 (2) | H15A—C15—H15B | 109.5 |
N4—C4—N3 | 117.1 (2) | O11—C15—H15C | 109.5 |
N4—C4—C5 | 120.0 (2) | H15A—C15—H15C | 109.5 |
N3—C4—C5 | 122.9 (2) | H15B—C15—H15C | 109.5 |
C6—C5—C4 | 115.4 (2) | O12—C16—H16A | 109.5 |
C6—C5—C7 | 121.1 (2) | O12—C16—H16B | 109.5 |
C4—C5—C7 | 122.8 (2) | H16A—C16—H16B | 109.5 |
C5—C6—N1 | 121.7 (2) | O12—C16—H16C | 109.5 |
C5—C6—H6 | 119.1 | H16A—C16—H16C | 109.5 |
N1—C6—H6 | 119.1 | H16B—C16—H16C | 109.5 |
C5—C7—C8 | 117.7 (2) | H1W—O1W—H2W | 105 (4) |
O2—C17—C18—C19 | 177.3 (3) | C6—C5—C7—C8 | 133.3 (3) |
O1—C17—C18—C19 | −2.4 (5) | C4—C5—C7—C8 | −56.5 (3) |
O2—C17—C18—S1 | −3.5 (3) | C5—C7—C8—C9 | −36.9 (4) |
O1—C17—C18—S1 | 176.7 (2) | C5—C7—C8—C13 | 144.5 (3) |
C21—S1—C18—C19 | 0.7 (2) | C13—C8—C9—C10 | −0.3 (4) |
C21—S1—C18—C17 | −178.6 (2) | C7—C8—C9—C10 | −178.9 (2) |
C17—C18—C19—C20 | 178.7 (3) | C14—O10—C10—C9 | −0.2 (4) |
S1—C18—C19—C20 | −0.5 (3) | C14—O10—C10—C11 | 179.7 (2) |
C17—C18—C19—Br1 | −1.6 (5) | C8—C9—C10—O10 | −178.7 (2) |
S1—C18—C19—Br1 | 179.20 (15) | C8—C9—C10—C11 | 1.4 (4) |
C18—C19—C20—C21 | −0.1 (4) | C15—O11—C11—C12 | −84.8 (3) |
Br1—C19—C20—C21 | −179.8 (2) | C15—O11—C11—C10 | 96.9 (3) |
C19—C20—C21—S1 | 0.6 (4) | O10—C10—C11—O11 | −2.7 (4) |
C18—S1—C21—C20 | −0.8 (3) | C9—C10—C11—O11 | 177.2 (2) |
C4—N3—C2—N2 | 176.7 (2) | O10—C10—C11—C12 | 179.0 (2) |
C4—N3—C2—N1 | −2.3 (4) | C9—C10—C11—C12 | −1.1 (4) |
C6—N1—C2—N2 | −178.2 (2) | C16—O12—C12—C11 | 177.6 (3) |
C6—N1—C2—N3 | 0.8 (4) | C16—O12—C12—C13 | −2.7 (4) |
C2—N3—C4—N4 | −174.2 (2) | O11—C11—C12—O12 | 1.1 (4) |
C2—N3—C4—C5 | 3.8 (3) | C10—C11—C12—O12 | 179.4 (2) |
N4—C4—C5—C6 | 174.2 (2) | O11—C11—C12—C13 | −178.7 (2) |
N3—C4—C5—C6 | −3.8 (3) | C10—C11—C12—C13 | −0.4 (4) |
N4—C4—C5—C7 | 3.5 (4) | C9—C8—C13—C12 | −1.2 (4) |
N3—C4—C5—C7 | −174.6 (2) | C7—C8—C13—C12 | 177.5 (2) |
C4—C5—C6—N1 | 2.3 (4) | O12—C12—C13—C8 | −178.2 (2) |
C7—C5—C6—N1 | 173.2 (2) | C11—C12—C13—C8 | 1.5 (4) |
C2—N1—C6—C5 | −0.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.99 | 2.757 (3) | 149 |
O1W—H1W···O1 | 0.82 (3) | 1.99 (3) | 2.772 (3) | 160 (4) |
N2—H2A···O1Wi | 0.86 | 2.58 | 3.159 (3) | 126 |
N2—H2A···O2 | 0.86 | 2.06 | 2.865 (4) | 155 |
N2—H2B···N3ii | 0.86 | 2.31 | 3.169 (3) | 176 |
O1W—H2W···O2iii | 0.82 (1) | 1.97 (2) | 2.698 (3) | 149 (4) |
N4—H4A···O1Wiv | 0.86 | 1.97 | 2.789 (3) | 157 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+1. |
C14H19N4O3+·C5H2ClO2S−·H2O | F(000) = 984 |
Mr = 470.92 | Dx = 1.450 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 16.9730 (5) Å | Cell parameters from 5309 reflections |
b = 6.8689 (1) Å | θ = 4.6–74.6° |
c = 19.6051 (5) Å | µ = 2.87 mm−1 |
β = 109.321 (3)° | T = 293 K |
V = 2156.95 (10) Å3 | Plate, colorless |
Z = 4 | 0.45 × 0.25 × 0.05 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 4105 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3455 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.052 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 70.1°, θmin = 4.7° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −8→7 |
Tmin = 0.440, Tmax = 1.000 | l = −23→23 |
14820 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0884P)2 + 0.4016P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4105 reflections | Δρmax = 0.46 e Å−3 |
289 parameters | Δρmin = −0.62 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.98170 (11) | 0.3357 (3) | 0.35457 (10) | 0.0388 (4) | |
H1 | 1.0070 | 0.3061 | 0.3245 | 0.047* | |
N2 | 1.03063 (13) | 0.0526 (3) | 0.41655 (12) | 0.0476 (5) | |
H2A | 1.0347 | −0.0270 | 0.4514 | 0.057* | |
H2B | 1.0560 | 0.0282 | 0.3861 | 0.057* | |
N3 | 0.94578 (10) | 0.2507 (2) | 0.45691 (9) | 0.0344 (4) | |
N4 | 0.87118 (12) | 0.4649 (3) | 0.50105 (10) | 0.0400 (4) | |
H4A | 0.8768 | 0.3865 | 0.5366 | 0.048* | |
H4B | 0.8442 | 0.5722 | 0.4984 | 0.048* | |
O10 | 0.56563 (10) | 0.5009 (2) | 0.32300 (10) | 0.0487 (4) | |
O11 | 0.52166 (9) | 0.8054 (3) | 0.38558 (9) | 0.0456 (4) | |
O12 | 0.63167 (11) | 1.0778 (2) | 0.45337 (10) | 0.0497 (4) | |
C2 | 0.98518 (12) | 0.2129 (3) | 0.40970 (11) | 0.0349 (4) | |
C4 | 0.90427 (11) | 0.4202 (3) | 0.45006 (11) | 0.0321 (4) | |
C5 | 0.89665 (12) | 0.5549 (3) | 0.39210 (11) | 0.0344 (4) | |
C6 | 0.93857 (13) | 0.5047 (3) | 0.34669 (11) | 0.0381 (4) | |
H6 | 0.9377 | 0.5884 | 0.3092 | 0.046* | |
C7 | 0.85643 (13) | 0.7520 (3) | 0.38753 (13) | 0.0400 (5) | |
H7A | 0.8577 | 0.8144 | 0.3435 | 0.048* | |
H7B | 0.8908 | 0.8297 | 0.4277 | 0.048* | |
C8 | 0.76692 (12) | 0.7595 (3) | 0.38814 (11) | 0.0355 (4) | |
C9 | 0.70883 (13) | 0.6185 (3) | 0.35332 (12) | 0.0369 (4) | |
H9 | 0.7245 | 0.5154 | 0.3299 | 0.044* | |
C10 | 0.62700 (12) | 0.6320 (3) | 0.35360 (11) | 0.0353 (4) | |
C11 | 0.60276 (12) | 0.7886 (3) | 0.38774 (11) | 0.0352 (4) | |
C12 | 0.66160 (14) | 0.9302 (3) | 0.42249 (12) | 0.0375 (4) | |
C13 | 0.74355 (13) | 0.9136 (3) | 0.42291 (13) | 0.0401 (5) | |
H13 | 0.7829 | 1.0066 | 0.4467 | 0.048* | |
C14 | 0.58610 (16) | 0.3370 (4) | 0.28783 (14) | 0.0498 (5) | |
H14B | 0.6072 | 0.3806 | 0.2507 | 0.075* | |
H14C | 0.5370 | 0.2594 | 0.2666 | 0.075* | |
H14A | 0.6279 | 0.2604 | 0.3224 | 0.075* | |
C15 | 0.50660 (19) | 0.7330 (6) | 0.44742 (17) | 0.0680 (8) | |
H15A | 0.4509 | 0.7665 | 0.4452 | 0.102* | |
H15C | 0.5459 | 0.7893 | 0.4900 | 0.102* | |
H15B | 0.5127 | 0.5940 | 0.4492 | 0.102* | |
C16 | 0.68977 (19) | 1.2218 (4) | 0.49211 (17) | 0.0591 (7) | |
H16B | 0.7137 | 1.2851 | 0.4600 | 0.089* | |
H16C | 0.7332 | 1.1609 | 0.5307 | 0.089* | |
H16A | 0.6615 | 1.3162 | 0.5118 | 0.089* | |
Cl1 | 1.22878 (4) | 0.63107 (9) | 0.25208 (4) | 0.0592 (2) | |
S1 | 1.32400 (4) | 0.10415 (10) | 0.35937 (4) | 0.0563 (2) | |
O1 | 1.10469 (11) | 0.3519 (2) | 0.29058 (10) | 0.0498 (4) | |
O2 | 1.15012 (14) | 0.0691 (3) | 0.34204 (14) | 0.0711 (6) | |
C17 | 1.16110 (15) | 0.2302 (3) | 0.31712 (13) | 0.0440 (5) | |
C18 | 1.24772 (14) | 0.2734 (3) | 0.31957 (12) | 0.0412 (5) | |
C19 | 1.28319 (15) | 0.4295 (3) | 0.29664 (13) | 0.0441 (5) | |
C20 | 1.37019 (16) | 0.4127 (4) | 0.31155 (15) | 0.0548 (6) | |
H20 | 1.4029 | 0.5061 | 0.2994 | 0.066* | |
C21 | 1.40008 (17) | 0.2433 (5) | 0.34582 (16) | 0.0605 (7) | |
H21 | 1.4560 | 0.2073 | 0.3603 | 0.073* | |
O1W | 1.11462 (16) | 0.6980 (3) | 0.36430 (11) | 0.0646 (6) | |
H1W | 1.128 (3) | 0.608 (4) | 0.343 (2) | 0.097* | |
H2W | 1.138 (3) | 0.795 (4) | 0.356 (2) | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0347 (9) | 0.0470 (10) | 0.0421 (9) | 0.0021 (7) | 0.0227 (7) | 0.0033 (7) |
N2 | 0.0495 (11) | 0.0425 (10) | 0.0639 (12) | 0.0104 (8) | 0.0364 (10) | 0.0074 (8) |
N3 | 0.0316 (8) | 0.0339 (8) | 0.0437 (9) | −0.0008 (7) | 0.0206 (7) | 0.0026 (7) |
N4 | 0.0416 (10) | 0.0395 (9) | 0.0485 (9) | 0.0042 (7) | 0.0280 (8) | 0.0056 (7) |
O10 | 0.0312 (7) | 0.0523 (9) | 0.0644 (10) | −0.0067 (7) | 0.0185 (7) | −0.0145 (8) |
O11 | 0.0290 (7) | 0.0581 (9) | 0.0545 (9) | 0.0033 (7) | 0.0201 (7) | 0.0001 (7) |
O12 | 0.0437 (9) | 0.0418 (8) | 0.0729 (11) | −0.0031 (7) | 0.0317 (8) | −0.0117 (7) |
C2 | 0.0287 (9) | 0.0363 (10) | 0.0441 (10) | −0.0025 (8) | 0.0179 (8) | 0.0009 (8) |
C4 | 0.0233 (9) | 0.0351 (9) | 0.0412 (10) | −0.0045 (7) | 0.0152 (8) | 0.0004 (7) |
C5 | 0.0237 (9) | 0.0389 (10) | 0.0444 (10) | −0.0011 (7) | 0.0165 (8) | 0.0059 (8) |
C6 | 0.0302 (9) | 0.0468 (11) | 0.0409 (10) | 0.0003 (8) | 0.0166 (8) | 0.0079 (8) |
C7 | 0.0304 (10) | 0.0382 (11) | 0.0566 (12) | 0.0006 (8) | 0.0214 (9) | 0.0076 (9) |
C8 | 0.0278 (9) | 0.0365 (10) | 0.0455 (10) | 0.0022 (8) | 0.0168 (8) | 0.0082 (8) |
C9 | 0.0301 (10) | 0.0382 (10) | 0.0457 (11) | 0.0027 (8) | 0.0169 (8) | 0.0012 (8) |
C10 | 0.0276 (9) | 0.0390 (10) | 0.0404 (10) | −0.0008 (8) | 0.0126 (8) | 0.0023 (8) |
C11 | 0.0248 (9) | 0.0417 (10) | 0.0419 (10) | 0.0022 (8) | 0.0149 (8) | 0.0047 (8) |
C12 | 0.0358 (10) | 0.0334 (10) | 0.0481 (11) | 0.0025 (8) | 0.0206 (9) | 0.0032 (8) |
C13 | 0.0319 (10) | 0.0363 (10) | 0.0545 (12) | −0.0041 (8) | 0.0176 (9) | 0.0011 (8) |
C14 | 0.0475 (13) | 0.0493 (13) | 0.0571 (13) | −0.0085 (11) | 0.0234 (11) | −0.0132 (10) |
C15 | 0.0516 (15) | 0.100 (2) | 0.0673 (17) | −0.0113 (15) | 0.0396 (14) | 0.0013 (15) |
C16 | 0.0621 (16) | 0.0473 (13) | 0.0799 (18) | −0.0127 (12) | 0.0396 (14) | −0.0173 (12) |
Cl1 | 0.0613 (4) | 0.0419 (3) | 0.0894 (5) | −0.0033 (2) | 0.0452 (4) | 0.0070 (3) |
S1 | 0.0533 (4) | 0.0574 (4) | 0.0641 (4) | 0.0006 (3) | 0.0274 (3) | 0.0102 (3) |
O1 | 0.0453 (9) | 0.0491 (9) | 0.0669 (10) | −0.0063 (7) | 0.0345 (8) | −0.0062 (7) |
O2 | 0.0744 (14) | 0.0432 (9) | 0.1214 (18) | −0.0098 (9) | 0.0671 (14) | 0.0078 (10) |
C17 | 0.0499 (13) | 0.0388 (11) | 0.0580 (13) | −0.0119 (10) | 0.0374 (11) | −0.0121 (9) |
C18 | 0.0434 (12) | 0.0406 (11) | 0.0474 (11) | −0.0077 (9) | 0.0257 (10) | −0.0062 (8) |
C19 | 0.0447 (12) | 0.0446 (11) | 0.0533 (12) | −0.0115 (9) | 0.0300 (10) | −0.0070 (9) |
C20 | 0.0424 (13) | 0.0637 (15) | 0.0664 (15) | −0.0143 (11) | 0.0288 (12) | −0.0027 (12) |
C21 | 0.0415 (13) | 0.0788 (19) | 0.0636 (16) | −0.0023 (12) | 0.0206 (12) | 0.0001 (13) |
O1W | 0.1063 (17) | 0.0404 (9) | 0.0718 (12) | −0.0043 (10) | 0.0627 (12) | −0.0007 (8) |
N1—C6 | 1.353 (3) | C9—H9 | 0.9300 |
N1—C2 | 1.357 (3) | C10—C11 | 1.399 (3) |
N1—H1 | 0.8600 | C11—C12 | 1.399 (3) |
N2—C2 | 1.326 (3) | C12—C13 | 1.393 (3) |
N2—H2A | 0.8600 | C13—H13 | 0.9300 |
N2—H2B | 0.8600 | C14—H14B | 0.9600 |
N3—C2 | 1.334 (3) | C14—H14C | 0.9600 |
N3—C4 | 1.344 (3) | C14—H14A | 0.9600 |
N4—C4 | 1.334 (3) | C15—H15A | 0.9600 |
N4—H4A | 0.8600 | C15—H15C | 0.9600 |
N4—H4B | 0.8600 | C15—H15B | 0.9600 |
O10—C10 | 1.357 (3) | C16—H16B | 0.9600 |
O10—C14 | 1.422 (3) | C16—H16C | 0.9600 |
O11—C11 | 1.368 (2) | C16—H16A | 0.9600 |
O11—C15 | 1.410 (3) | Cl1—C19 | 1.732 (3) |
O12—C12 | 1.362 (3) | S1—C21 | 1.697 (3) |
O12—C16 | 1.426 (3) | S1—C18 | 1.723 (2) |
C4—C5 | 1.438 (3) | O1—C17 | 1.248 (3) |
C5—C6 | 1.355 (3) | O2—C17 | 1.249 (3) |
C5—C7 | 1.506 (3) | C17—C18 | 1.485 (3) |
C6—H6 | 0.9300 | C18—C19 | 1.376 (3) |
C7—C8 | 1.524 (3) | C19—C20 | 1.412 (4) |
C7—H7A | 0.9700 | C20—C21 | 1.355 (4) |
C7—H7B | 0.9700 | C20—H20 | 0.9300 |
C8—C13 | 1.386 (3) | C21—H21 | 0.9300 |
C8—C9 | 1.390 (3) | O1W—H1W | 0.819 (10) |
C9—C10 | 1.394 (3) | O1W—H2W | 0.822 (10) |
C6—N1—C2 | 120.22 (17) | C10—C11—C12 | 119.46 (18) |
C6—N1—H1 | 119.9 | O12—C12—C13 | 125.2 (2) |
C2—N1—H1 | 119.9 | O12—C12—C11 | 115.00 (18) |
C2—N2—H2A | 120.0 | C13—C12—C11 | 119.78 (19) |
C2—N2—H2B | 120.0 | C8—C13—C12 | 120.5 (2) |
H2A—N2—H2B | 120.0 | C8—C13—H13 | 119.8 |
C2—N3—C4 | 117.75 (17) | C12—C13—H13 | 119.8 |
C4—N4—H4A | 120.0 | O10—C14—H14B | 109.5 |
C4—N4—H4B | 120.0 | O10—C14—H14C | 109.5 |
H4A—N4—H4B | 120.0 | H14B—C14—H14C | 109.5 |
C10—O10—C14 | 117.70 (17) | O10—C14—H14A | 109.5 |
C11—O11—C15 | 114.24 (19) | H14B—C14—H14A | 109.5 |
C12—O12—C16 | 117.34 (19) | H14C—C14—H14A | 109.5 |
N2—C2—N3 | 119.99 (19) | O11—C15—H15A | 109.5 |
N2—C2—N1 | 117.88 (18) | O11—C15—H15C | 109.5 |
N3—C2—N1 | 122.12 (19) | H15A—C15—H15C | 109.5 |
N4—C4—N3 | 117.46 (18) | O11—C15—H15B | 109.5 |
N4—C4—C5 | 119.59 (18) | H15A—C15—H15B | 109.5 |
N3—C4—C5 | 122.92 (17) | H15C—C15—H15B | 109.5 |
C6—C5—C4 | 115.20 (18) | O12—C16—H16B | 109.5 |
C6—C5—C7 | 121.06 (18) | O12—C16—H16C | 109.5 |
C4—C5—C7 | 123.11 (18) | H16B—C16—H16C | 109.5 |
N1—C6—C5 | 121.67 (18) | O12—C16—H16A | 109.5 |
N1—C6—H6 | 119.2 | H16B—C16—H16A | 109.5 |
C5—C6—H6 | 119.2 | H16C—C16—H16A | 109.5 |
C5—C7—C8 | 117.59 (17) | C21—S1—C18 | 92.62 (13) |
C5—C7—H7A | 107.9 | O1—C17—O2 | 124.3 (2) |
C8—C7—H7A | 107.9 | O1—C17—C18 | 119.6 (2) |
C5—C7—H7B | 107.9 | O2—C17—C18 | 116.0 (2) |
C8—C7—H7B | 107.9 | C19—C18—C17 | 132.9 (2) |
H7A—C7—H7B | 107.2 | C19—C18—S1 | 109.24 (18) |
C13—C8—C9 | 120.12 (19) | C17—C18—S1 | 117.86 (17) |
C13—C8—C7 | 118.54 (19) | C18—C19—C20 | 114.1 (2) |
C9—C8—C7 | 121.32 (19) | C18—C19—Cl1 | 124.75 (19) |
C8—C9—C10 | 119.84 (19) | C20—C19—Cl1 | 121.10 (18) |
C8—C9—H9 | 120.1 | C21—C20—C19 | 111.5 (2) |
C10—C9—H9 | 120.1 | C21—C20—H20 | 124.2 |
O10—C10—C9 | 125.02 (19) | C19—C20—H20 | 124.2 |
O10—C10—C11 | 114.68 (18) | C20—C21—S1 | 112.4 (2) |
C9—C10—C11 | 120.30 (19) | C20—C21—H21 | 123.8 |
O11—C11—C10 | 120.17 (19) | S1—C21—H21 | 123.8 |
O11—C11—C12 | 120.35 (19) | H1W—O1W—H2W | 106 (4) |
C4—N3—C2—N2 | 176.4 (2) | O10—C10—C11—C12 | 178.58 (18) |
C4—N3—C2—N1 | −2.5 (3) | C9—C10—C11—C12 | −0.9 (3) |
C6—N1—C2—N2 | −177.7 (2) | C16—O12—C12—C13 | −3.1 (3) |
C6—N1—C2—N3 | 1.2 (3) | C16—O12—C12—C11 | 177.4 (2) |
C2—N3—C4—N4 | −174.28 (18) | O11—C11—C12—O12 | 0.9 (3) |
C2—N3—C4—C5 | 3.8 (3) | C10—C11—C12—O12 | 179.28 (18) |
N4—C4—C5—C6 | 174.32 (19) | O11—C11—C12—C13 | −178.57 (19) |
N3—C4—C5—C6 | −3.7 (3) | C10—C11—C12—C13 | −0.2 (3) |
N4—C4—C5—C7 | 3.3 (3) | C9—C8—C13—C12 | −0.9 (3) |
N3—C4—C5—C7 | −174.76 (18) | C7—C8—C13—C12 | 177.58 (19) |
C2—N1—C6—C5 | −1.2 (3) | O12—C12—C13—C8 | −178.3 (2) |
C4—C5—C6—N1 | 2.3 (3) | C11—C12—C13—C8 | 1.1 (3) |
C7—C5—C6—N1 | 173.58 (19) | O1—C17—C18—C19 | −0.9 (4) |
C6—C5—C7—C8 | 132.8 (2) | O2—C17—C18—C19 | 178.5 (3) |
C4—C5—C7—C8 | −56.6 (3) | O1—C17—C18—S1 | 177.95 (17) |
C5—C7—C8—C13 | 144.5 (2) | O2—C17—C18—S1 | −2.7 (3) |
C5—C7—C8—C9 | −37.0 (3) | C21—S1—C18—C19 | 0.64 (19) |
C13—C8—C9—C10 | −0.2 (3) | C21—S1—C18—C17 | −178.45 (18) |
C7—C8—C9—C10 | −178.61 (18) | C17—C18—C19—C20 | 178.4 (2) |
C14—O10—C10—C9 | −0.1 (3) | S1—C18—C19—C20 | −0.5 (3) |
C14—O10—C10—C11 | −179.5 (2) | C17—C18—C19—Cl1 | −2.4 (4) |
C8—C9—C10—O10 | −178.3 (2) | S1—C18—C19—Cl1 | 178.67 (13) |
C8—C9—C10—C11 | 1.1 (3) | C18—C19—C20—C21 | 0.0 (3) |
C15—O11—C11—C10 | 97.3 (3) | Cl1—C19—C20—C21 | −179.2 (2) |
C15—O11—C11—C12 | −84.3 (3) | C19—C20—C21—S1 | 0.5 (3) |
O10—C10—C11—O11 | −3.0 (3) | C18—S1—C21—C20 | −0.7 (2) |
C9—C10—C11—O11 | 177.52 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 2.01 | 2.771 (3) | 148 |
O1W—H1W···O1 | 0.82 (4) | 2.01 (3) | 2.758 (3) | 152 (5) |
N2—H2A···N3i | 0.86 | 2.30 | 3.162 (3) | 176 |
N2—H2B···O1Wii | 0.86 | 2.57 | 3.159 (3) | 127 |
N2—H2B···O2 | 0.86 | 2.07 | 2.867 (3) | 154 |
O1W—H2W···O2iii | 0.82 (4) | 1.92 (3) | 2.688 (3) | 155 (5) |
N4—H4A···O1Wiv | 0.86 | 1.99 | 2.803 (3) | 158 |
C6—H6···O1v | 0.93 | 2.59 | 3.487 (3) | 163 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+2, −y+1, −z+1; (v) −x+2, y+1/2, −z+1/2. |
C14H19N4O3+·C6H5O2S−·H2O | Z = 2 |
Mr = 450.51 | F(000) = 476 |
Triclinic, P1 | Dx = 1.365 Mg m−3 |
a = 6.9417 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.8281 (6) Å | Cell parameters from 3402 reflections |
c = 16.2754 (10) Å | θ = 4.5–74.3° |
α = 90.813 (5)° | µ = 1.70 mm−1 |
β = 90.376 (4)° | T = 293 K |
γ = 99.084 (4)° | Prism, colorless |
V = 1096.29 (11) Å3 | 0.35 × 0.25 × 0.15 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 4155 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3502 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.023 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 70.1°, θmin = 4.6° |
ω scans | h = −6→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −11→11 |
Tmin = 0.335, Tmax = 1.000 | l = −19→19 |
7519 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0657P)2 + 0.191P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.118 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.23 e Å−3 |
4155 reflections | Δρmin = −0.26 e Å−3 |
285 parameters | Extinction correction: SHELXT (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0102 (8) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.2859 (2) | 0.28247 (14) | 0.09902 (9) | 0.0406 (3) | |
H1 | 0.2386 | 0.1963 | 0.1016 | 0.049* | |
N2 | 0.0052 (2) | 0.32154 (15) | 0.03457 (10) | 0.0465 (4) | |
H2A | −0.0652 | 0.3764 | 0.0130 | 0.056* | |
H2B | −0.0381 | 0.2347 | 0.0365 | 0.056* | |
N3 | 0.24574 (18) | 0.50579 (13) | 0.06134 (8) | 0.0335 (3) | |
N4 | 0.4863 (2) | 0.68792 (14) | 0.08831 (9) | 0.0426 (3) | |
H4A | 0.4135 | 0.7403 | 0.0658 | 0.051* | |
H4B | 0.5991 | 0.7227 | 0.1077 | 0.051* | |
O10 | 0.46033 (18) | 0.61576 (14) | 0.43249 (8) | 0.0491 (3) | |
O11 | 0.7951 (2) | 0.77575 (13) | 0.47759 (7) | 0.0493 (3) | |
O12 | 1.09591 (18) | 0.82209 (14) | 0.37553 (8) | 0.0537 (4) | |
C2 | 0.1804 (2) | 0.37076 (16) | 0.06482 (9) | 0.0342 (3) | |
C4 | 0.4245 (2) | 0.55373 (16) | 0.09306 (9) | 0.0323 (3) | |
C5 | 0.5453 (2) | 0.46392 (17) | 0.12840 (9) | 0.0347 (3) | |
C6 | 0.4675 (3) | 0.32957 (17) | 0.12951 (10) | 0.0393 (4) | |
H6 | 0.5401 | 0.2670 | 0.1518 | 0.047* | |
C7 | 0.7450 (2) | 0.5151 (2) | 0.16288 (10) | 0.0414 (4) | |
H7A | 0.8156 | 0.5773 | 0.1238 | 0.050* | |
H7B | 0.8140 | 0.4372 | 0.1683 | 0.050* | |
C8 | 0.7490 (2) | 0.58913 (17) | 0.24565 (10) | 0.0356 (4) | |
C9 | 0.5932 (2) | 0.56625 (17) | 0.29904 (10) | 0.0369 (4) | |
H9 | 0.4797 | 0.5079 | 0.2834 | 0.044* | |
C10 | 0.6065 (2) | 0.63051 (17) | 0.37606 (10) | 0.0361 (4) | |
C11 | 0.7771 (2) | 0.71709 (17) | 0.39997 (10) | 0.0372 (4) | |
C12 | 0.9335 (2) | 0.73845 (17) | 0.34612 (11) | 0.0391 (4) | |
C13 | 0.9189 (2) | 0.67615 (18) | 0.26875 (11) | 0.0395 (4) | |
H13 | 1.0226 | 0.6926 | 0.2325 | 0.047* | |
C14 | 0.2941 (3) | 0.5146 (2) | 0.41586 (12) | 0.0522 (5) | |
H14A | 0.2295 | 0.5384 | 0.3670 | 0.078* | |
H14B | 0.2060 | 0.5107 | 0.4613 | 0.078* | |
H14C | 0.3344 | 0.4263 | 0.4080 | 0.078* | |
C15 | 0.7364 (5) | 0.9061 (3) | 0.48353 (16) | 0.0801 (8) | |
H15A | 0.7964 | 0.9637 | 0.4406 | 0.120* | |
H15B | 0.7757 | 0.9475 | 0.5360 | 0.120* | |
H15C | 0.5971 | 0.8960 | 0.4780 | 0.120* | |
C16 | 1.2567 (3) | 0.8507 (2) | 0.32168 (14) | 0.0557 (5) | |
H16A | 1.2202 | 0.9007 | 0.2753 | 0.084* | |
H16B | 1.2945 | 0.7657 | 0.3030 | 0.084* | |
H16C | 1.3642 | 0.9051 | 0.3503 | 0.084* | |
S1 | −0.00942 (7) | 0.16614 (5) | 0.27384 (3) | 0.05197 (17) | |
O1 | 0.12536 (19) | 0.01871 (13) | 0.13135 (9) | 0.0504 (3) | |
O2 | −0.1574 (2) | −0.11389 (16) | 0.10099 (9) | 0.0626 (4) | |
C17 | −0.0560 (3) | −0.02140 (17) | 0.14159 (11) | 0.0422 (4) | |
C18 | −0.1493 (3) | 0.05097 (18) | 0.20791 (11) | 0.0435 (4) | |
C19 | −0.3406 (3) | 0.0421 (2) | 0.22606 (13) | 0.0514 (5) | |
H19 | −0.4393 | −0.0151 | 0.1977 | 0.062* | |
C20 | −0.3753 (3) | 0.1290 (2) | 0.29276 (13) | 0.0535 (5) | |
H20 | −0.4996 | 0.1354 | 0.3119 | 0.064* | |
C21 | −0.2101 (3) | 0.2021 (2) | 0.32632 (12) | 0.0483 (4) | |
C22 | −0.1899 (4) | 0.2992 (2) | 0.39856 (14) | 0.0623 (5) | |
H22A | −0.1024 | 0.2703 | 0.4382 | 0.093* | |
H22B | −0.3153 | 0.2992 | 0.4230 | 0.093* | |
H22C | −0.1390 | 0.3905 | 0.3808 | 0.093* | |
O1W | 0.3108 (2) | 0.90308 (16) | 0.01268 (9) | 0.0637 (4) | |
H1W | 0.2512 | 0.9381 | 0.0492 | 0.096* | |
H2W | 0.4143 | 0.9593 | 0.0158 | 0.096* | 0.5 |
H3W | 0.3042 | 0.9550 | −0.0264 | 0.096* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0471 (8) | 0.0258 (7) | 0.0462 (8) | −0.0025 (6) | −0.0023 (6) | −0.0009 (6) |
N2 | 0.0434 (8) | 0.0314 (7) | 0.0602 (10) | −0.0075 (6) | −0.0107 (7) | −0.0032 (6) |
N3 | 0.0346 (7) | 0.0267 (6) | 0.0366 (7) | −0.0024 (5) | −0.0017 (5) | −0.0024 (5) |
N4 | 0.0408 (7) | 0.0296 (7) | 0.0536 (9) | −0.0052 (6) | −0.0083 (6) | −0.0029 (6) |
O10 | 0.0446 (7) | 0.0587 (8) | 0.0395 (7) | −0.0054 (6) | 0.0061 (5) | −0.0083 (6) |
O11 | 0.0625 (8) | 0.0473 (7) | 0.0359 (6) | 0.0028 (6) | −0.0089 (6) | −0.0083 (5) |
O12 | 0.0427 (7) | 0.0562 (8) | 0.0549 (8) | −0.0135 (6) | −0.0073 (6) | −0.0103 (6) |
C2 | 0.0380 (8) | 0.0301 (8) | 0.0320 (8) | −0.0019 (6) | 0.0017 (6) | −0.0041 (6) |
C4 | 0.0346 (8) | 0.0306 (8) | 0.0291 (7) | −0.0024 (6) | 0.0021 (6) | −0.0058 (6) |
C5 | 0.0364 (8) | 0.0377 (8) | 0.0291 (7) | 0.0040 (7) | 0.0009 (6) | −0.0054 (6) |
C6 | 0.0464 (9) | 0.0350 (8) | 0.0370 (8) | 0.0080 (7) | −0.0027 (7) | −0.0014 (6) |
C7 | 0.0350 (8) | 0.0509 (10) | 0.0378 (9) | 0.0057 (7) | −0.0015 (7) | −0.0077 (7) |
C8 | 0.0344 (8) | 0.0369 (8) | 0.0353 (8) | 0.0051 (6) | −0.0038 (6) | −0.0015 (6) |
C9 | 0.0322 (8) | 0.0395 (9) | 0.0371 (8) | 0.0003 (6) | −0.0053 (6) | −0.0040 (7) |
C10 | 0.0349 (8) | 0.0377 (8) | 0.0350 (8) | 0.0038 (6) | −0.0004 (6) | 0.0006 (6) |
C11 | 0.0424 (9) | 0.0353 (8) | 0.0331 (8) | 0.0038 (7) | −0.0071 (7) | −0.0032 (6) |
C12 | 0.0355 (8) | 0.0354 (8) | 0.0438 (9) | −0.0023 (7) | −0.0080 (7) | −0.0004 (7) |
C13 | 0.0323 (8) | 0.0427 (9) | 0.0418 (9) | 0.0009 (7) | −0.0010 (7) | −0.0011 (7) |
C14 | 0.0451 (10) | 0.0583 (12) | 0.0480 (10) | −0.0082 (9) | 0.0069 (8) | 0.0003 (9) |
C15 | 0.118 (2) | 0.0599 (15) | 0.0661 (15) | 0.0277 (14) | −0.0115 (14) | −0.0236 (12) |
C16 | 0.0392 (9) | 0.0527 (11) | 0.0698 (13) | −0.0094 (8) | −0.0072 (9) | 0.0030 (10) |
S1 | 0.0426 (3) | 0.0530 (3) | 0.0588 (3) | 0.0041 (2) | −0.0025 (2) | −0.0106 (2) |
O1 | 0.0496 (7) | 0.0336 (6) | 0.0649 (8) | −0.0025 (5) | 0.0091 (6) | −0.0050 (6) |
O2 | 0.0618 (9) | 0.0577 (9) | 0.0601 (9) | −0.0146 (7) | −0.0024 (7) | −0.0132 (7) |
C17 | 0.0480 (10) | 0.0316 (8) | 0.0449 (9) | −0.0009 (7) | 0.0001 (7) | 0.0050 (7) |
C18 | 0.0455 (9) | 0.0363 (9) | 0.0469 (10) | 0.0004 (7) | −0.0011 (8) | 0.0056 (7) |
C19 | 0.0451 (10) | 0.0473 (11) | 0.0584 (11) | −0.0035 (8) | 0.0004 (8) | 0.0037 (9) |
C20 | 0.0460 (10) | 0.0531 (11) | 0.0610 (12) | 0.0051 (9) | 0.0103 (9) | 0.0061 (9) |
C21 | 0.0545 (10) | 0.0436 (10) | 0.0474 (10) | 0.0093 (8) | 0.0026 (8) | 0.0061 (8) |
C22 | 0.0682 (13) | 0.0621 (13) | 0.0588 (13) | 0.0177 (11) | −0.0012 (10) | −0.0072 (10) |
O1W | 0.0704 (9) | 0.0620 (9) | 0.0617 (9) | 0.0204 (7) | 0.0031 (7) | −0.0059 (7) |
N1—C2 | 1.344 (2) | C11—C12 | 1.391 (2) |
N1—C6 | 1.360 (2) | C12—C13 | 1.389 (2) |
N1—H1 | 0.8600 | C13—H13 | 0.9300 |
N2—C2 | 1.325 (2) | C14—H14A | 0.9600 |
N2—H2A | 0.8600 | C14—H14B | 0.9600 |
N2—H2B | 0.8600 | C14—H14C | 0.9600 |
N3—C2 | 1.335 (2) | C15—H15A | 0.9600 |
N3—C4 | 1.3524 (19) | C15—H15B | 0.9600 |
N4—C4 | 1.324 (2) | C15—H15C | 0.9600 |
N4—H4A | 0.8600 | C16—H16A | 0.9600 |
N4—H4B | 0.8600 | C16—H16B | 0.9600 |
O10—C10 | 1.365 (2) | C16—H16C | 0.9600 |
O10—C14 | 1.421 (2) | S1—C21 | 1.720 (2) |
O11—C11 | 1.378 (2) | S1—C18 | 1.7263 (18) |
O11—C15 | 1.406 (3) | O1—C17 | 1.271 (2) |
O12—C12 | 1.3657 (19) | O2—C17 | 1.238 (2) |
O12—C16 | 1.419 (2) | C17—C18 | 1.491 (3) |
C4—C5 | 1.433 (2) | C18—C19 | 1.352 (3) |
C5—C6 | 1.346 (2) | C19—C20 | 1.416 (3) |
C5—C7 | 1.500 (2) | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—C21 | 1.361 (3) |
C7—C8 | 1.520 (2) | C20—H20 | 0.9300 |
C7—H7A | 0.9700 | C21—C22 | 1.496 (3) |
C7—H7B | 0.9700 | C22—H22A | 0.9600 |
C8—C9 | 1.384 (2) | C22—H22B | 0.9600 |
C8—C13 | 1.389 (2) | C22—H22C | 0.9600 |
C9—C10 | 1.392 (2) | O1W—H1W | 0.8280 |
C9—H9 | 0.9300 | O1W—H2W | 0.8353 |
C10—C11 | 1.394 (2) | O1W—H3W | 0.8274 |
C2—N1—C6 | 119.91 (14) | C12—C13—C8 | 119.85 (16) |
C2—N1—H1 | 120.0 | C12—C13—H13 | 120.1 |
C6—N1—H1 | 120.0 | C8—C13—H13 | 120.1 |
C2—N2—H2A | 120.0 | O10—C14—H14A | 109.5 |
C2—N2—H2B | 120.0 | O10—C14—H14B | 109.5 |
H2A—N2—H2B | 120.0 | H14A—C14—H14B | 109.5 |
C2—N3—C4 | 118.24 (14) | O10—C14—H14C | 109.5 |
C4—N4—H4A | 120.0 | H14A—C14—H14C | 109.5 |
C4—N4—H4B | 120.0 | H14B—C14—H14C | 109.5 |
H4A—N4—H4B | 120.0 | O11—C15—H15A | 109.5 |
C10—O10—C14 | 117.58 (13) | O11—C15—H15B | 109.5 |
C11—O11—C15 | 114.42 (15) | H15A—C15—H15B | 109.5 |
C12—O12—C16 | 117.23 (14) | O11—C15—H15C | 109.5 |
N2—C2—N3 | 119.32 (15) | H15A—C15—H15C | 109.5 |
N2—C2—N1 | 118.53 (14) | H15B—C15—H15C | 109.5 |
N3—C2—N1 | 122.15 (14) | O12—C16—H16A | 109.5 |
N4—C4—N3 | 116.99 (15) | O12—C16—H16B | 109.5 |
N4—C4—C5 | 120.98 (14) | H16A—C16—H16B | 109.5 |
N3—C4—C5 | 122.00 (14) | O12—C16—H16C | 109.5 |
C6—C5—C4 | 115.67 (14) | H16A—C16—H16C | 109.5 |
C6—C5—C7 | 121.61 (16) | H16B—C16—H16C | 109.5 |
C4—C5—C7 | 122.71 (15) | C21—S1—C18 | 92.79 (9) |
C5—C6—N1 | 121.99 (16) | O2—C17—O1 | 125.02 (18) |
C5—C6—H6 | 119.0 | O2—C17—C18 | 119.02 (17) |
N1—C6—H6 | 119.0 | O1—C17—C18 | 115.95 (15) |
C5—C7—C8 | 115.21 (14) | C19—C18—C17 | 128.91 (17) |
C5—C7—H7A | 108.5 | C19—C18—S1 | 110.47 (15) |
C8—C7—H7A | 108.5 | C17—C18—S1 | 120.62 (13) |
C5—C7—H7B | 108.5 | C18—C19—C20 | 113.03 (18) |
C8—C7—H7B | 108.5 | C18—C19—H19 | 123.5 |
H7A—C7—H7B | 107.5 | C20—C19—H19 | 123.5 |
C9—C8—C13 | 120.17 (15) | C21—C20—C19 | 113.82 (18) |
C9—C8—C7 | 121.74 (14) | C21—C20—H20 | 123.1 |
C13—C8—C7 | 118.01 (15) | C19—C20—H20 | 123.1 |
C8—C9—C10 | 120.00 (14) | C20—C21—C22 | 128.68 (19) |
C8—C9—H9 | 120.0 | C20—C21—S1 | 109.88 (15) |
C10—C9—H9 | 120.0 | C22—C21—S1 | 121.43 (16) |
O10—C10—C9 | 124.33 (14) | C21—C22—H22A | 109.5 |
O10—C10—C11 | 115.49 (14) | C21—C22—H22B | 109.5 |
C9—C10—C11 | 120.19 (15) | H22A—C22—H22B | 109.5 |
O11—C11—C12 | 119.99 (15) | C21—C22—H22C | 109.5 |
O11—C11—C10 | 120.57 (15) | H22A—C22—H22C | 109.5 |
C12—C11—C10 | 119.36 (15) | H22B—C22—H22C | 109.5 |
O12—C12—C13 | 124.34 (16) | H1W—O1W—H2W | 97.3 |
O12—C12—C11 | 115.25 (15) | H1W—O1W—H3W | 102.7 |
C13—C12—C11 | 120.41 (15) | H2W—O1W—H3W | 75.7 |
C4—N3—C2—N2 | 179.61 (14) | C9—C10—C11—O11 | −176.79 (15) |
C4—N3—C2—N1 | 0.4 (2) | O10—C10—C11—C12 | −179.77 (15) |
C6—N1—C2—N2 | 179.02 (15) | C9—C10—C11—C12 | 0.0 (2) |
C6—N1—C2—N3 | −1.8 (2) | C16—O12—C12—C13 | 2.6 (3) |
C2—N3—C4—N4 | 179.57 (14) | C16—O12—C12—C11 | −177.86 (16) |
C2—N3—C4—C5 | 1.2 (2) | O11—C11—C12—O12 | −1.7 (2) |
N4—C4—C5—C6 | −179.68 (15) | C10—C11—C12—O12 | −178.49 (15) |
N3—C4—C5—C6 | −1.4 (2) | O11—C11—C12—C13 | 177.90 (15) |
N4—C4—C5—C7 | 0.9 (2) | C10—C11—C12—C13 | 1.1 (3) |
N3—C4—C5—C7 | 179.19 (14) | O12—C12—C13—C8 | 177.92 (16) |
C4—C5—C6—N1 | 0.0 (2) | C11—C12—C13—C8 | −1.6 (3) |
C7—C5—C6—N1 | 179.43 (14) | C9—C8—C13—C12 | 1.1 (3) |
C2—N1—C6—C5 | 1.5 (3) | C7—C8—C13—C12 | −175.63 (16) |
C6—C5—C7—C8 | −104.60 (19) | O2—C17—C18—C19 | −8.5 (3) |
C4—C5—C7—C8 | 74.8 (2) | O1—C17—C18—C19 | 171.34 (19) |
C5—C7—C8—C9 | 23.7 (2) | O2—C17—C18—S1 | 172.41 (15) |
C5—C7—C8—C13 | −159.62 (16) | O1—C17—C18—S1 | −7.8 (2) |
C13—C8—C9—C10 | 0.0 (3) | C21—S1—C18—C19 | 0.16 (15) |
C7—C8—C9—C10 | 176.59 (16) | C21—S1—C18—C17 | 179.42 (15) |
C14—O10—C10—C9 | 8.6 (3) | C17—C18—C19—C20 | −178.71 (17) |
C14—O10—C10—C11 | −171.61 (16) | S1—C18—C19—C20 | 0.5 (2) |
C8—C9—C10—O10 | 179.19 (16) | C18—C19—C20—C21 | −1.1 (3) |
C8—C9—C10—C11 | −0.6 (3) | C19—C20—C21—C22 | −177.7 (2) |
C15—O11—C11—C12 | 91.7 (2) | C19—C20—C21—S1 | 1.2 (2) |
C15—O11—C11—C10 | −91.5 (2) | C18—S1—C21—C20 | −0.77 (15) |
O10—C10—C11—O11 | 3.4 (2) | C18—S1—C21—C22 | 178.18 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.87 | 2.7153 (19) | 167 |
O1W—H1W···O1i | 0.83 | 1.84 | 2.667 (2) | 178 |
N2—H2A···N3ii | 0.86 | 2.20 | 3.054 (2) | 170 |
N2—H2B···O1Wii | 0.86 | 2.28 | 2.946 (2) | 134 |
O1W—H2W···O1Wiii | 0.84 | 2.21 | 3.026 (2) | 164 |
O1W—H3W···O2ii | 0.83 | 2.34 | 3.103 (2) | 153 |
N4—H4A···O1W | 0.86 | 2.05 | 2.888 (2) | 164 |
N4—H4B···O2iv | 0.86 | 2.14 | 2.901 (2) | 147 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) x+1, y+1, z. |
2C14H19N4O3+·2C15H9O2−·3(H2O) | Z = 2 |
Mr = 1079.15 | F(000) = 1140 |
Triclinic, P1 | Dx = 1.298 Mg m−3 |
a = 11.1680 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.1913 (5) Å | Cell parameters from 6949 reflections |
c = 16.2434 (5) Å | θ = 3.2–27.3° |
α = 106.203 (3)° | µ = 0.09 mm−1 |
β = 101.386 (3)° | T = 293 K |
γ = 90.029 (3)° | Prism, yellow |
V = 2760.20 (18) Å3 | 0.40 × 0.30 × 0.10 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 12640 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 7531 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω scans | h = −14→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −19→21 |
Tmin = 0.755, Tmax = 1.000 | l = −21→20 |
29344 measured reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.189 | w = 1/[σ2(Fo2) + (0.0784P)2 + 0.7983P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
12640 reflections | Δρmax = 0.44 e Å−3 |
742 parameters | Δρmin = −0.36 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.42349 (16) | 0.63275 (11) | 0.36066 (11) | 0.0443 (4) | |
H1A | 0.4782 | 0.6702 | 0.3607 | 0.053* | |
N2A | 0.55873 (17) | 0.58920 (13) | 0.46403 (12) | 0.0520 (5) | |
H2A | 0.5761 | 0.5579 | 0.4992 | 0.062* | |
H2B | 0.6134 | 0.6252 | 0.4612 | 0.062* | |
N3A | 0.36439 (16) | 0.52609 (11) | 0.41934 (11) | 0.0420 (4) | |
N4A | 0.16927 (19) | 0.46738 (14) | 0.37770 (13) | 0.0605 (6) | |
H4A | 0.1877 | 0.4386 | 0.4152 | 0.073* | |
H4B | 0.0966 | 0.4618 | 0.3462 | 0.073* | |
O10A | 0.11712 (17) | 0.59173 (11) | −0.04154 (11) | 0.0618 (5) | |
O11A | 0.00987 (17) | 0.73737 (12) | −0.00709 (12) | 0.0695 (5) | |
O12A | −0.06035 (19) | 0.80335 (12) | 0.14574 (15) | 0.0816 (6) | |
C2A | 0.44835 (19) | 0.58204 (13) | 0.41443 (13) | 0.0394 (4) | |
C4A | 0.25279 (19) | 0.52017 (13) | 0.36841 (13) | 0.0413 (5) | |
C5A | 0.22347 (19) | 0.56872 (14) | 0.30614 (13) | 0.0417 (5) | |
C6A | 0.3118 (2) | 0.62481 (14) | 0.30626 (14) | 0.0449 (5) | |
H6C | 0.2966 | 0.6591 | 0.2684 | 0.054* | |
C7A | 0.0973 (2) | 0.55594 (18) | 0.24789 (15) | 0.0569 (6) | |
H7C | 0.0818 | 0.4952 | 0.2168 | 0.068* | |
H7D | 0.0376 | 0.5716 | 0.2848 | 0.068* | |
C8A | 0.0767 (2) | 0.60631 (16) | 0.18165 (14) | 0.0487 (5) | |
C9A | 0.1128 (2) | 0.57437 (15) | 0.10240 (14) | 0.0477 (5) | |
H9A | 0.1540 | 0.5238 | 0.0917 | 0.057* | |
C10A | 0.0876 (2) | 0.61785 (15) | 0.03898 (14) | 0.0462 (5) | |
C11A | 0.0269 (2) | 0.69351 (15) | 0.05536 (15) | 0.0497 (5) | |
C12A | −0.0064 (2) | 0.72650 (15) | 0.13520 (17) | 0.0541 (6) | |
C13A | 0.0177 (2) | 0.68258 (17) | 0.19813 (16) | 0.0559 (6) | |
H13A | −0.0058 | 0.7044 | 0.2515 | 0.067* | |
C14A | 0.1890 (3) | 0.51853 (18) | −0.05974 (19) | 0.0694 (7) | |
H14A | 0.2084 | 0.5098 | −0.1164 | 0.104* | |
H14B | 0.1436 | 0.4685 | −0.0590 | 0.104* | |
H14C | 0.2632 | 0.5281 | −0.0161 | 0.104* | |
C15 | −0.1131 (3) | 0.7388 (3) | −0.0508 (3) | 0.1212 (15) | |
H15A | −0.1473 | 0.6808 | −0.0772 | 0.182* | |
H15B | −0.1151 | 0.7675 | −0.0954 | 0.182* | |
H15C | −0.1599 | 0.7690 | −0.0094 | 0.182* | |
C16 | −0.1003 (3) | 0.8407 (2) | 0.2258 (3) | 0.1082 (13) | |
H16A | −0.0332 | 0.8462 | 0.2745 | 0.162* | |
H16B | −0.1652 | 0.8043 | 0.2304 | 0.162* | |
H16C | −0.1294 | 0.8966 | 0.2264 | 0.162* | |
N1B | 0.81669 (18) | 0.17705 (12) | 0.24088 (11) | 0.0487 (5) | |
H1B | 0.8123 | 0.2112 | 0.2084 | 0.058* | |
N2B | 1.00200 (18) | 0.24533 (13) | 0.32005 (13) | 0.0540 (5) | |
H2C | 1.0655 | 0.2506 | 0.3613 | 0.065* | |
H2D | 0.9948 | 0.2797 | 0.2876 | 0.065* | |
N3B | 0.92672 (16) | 0.13168 (11) | 0.35652 (11) | 0.0449 (4) | |
N4B | 0.84917 (18) | 0.02136 (13) | 0.39536 (12) | 0.0557 (5) | |
H4C | 0.9140 | 0.0273 | 0.4356 | 0.067* | |
H4D | 0.7929 | −0.0176 | 0.3889 | 0.067* | |
O10B | 0.43317 (18) | −0.13067 (12) | −0.04335 (11) | 0.0677 (5) | |
O11B | 0.24001 (17) | −0.03684 (13) | −0.02539 (11) | 0.0709 (5) | |
O12B | 0.21985 (18) | 0.06858 (14) | 0.13037 (13) | 0.0767 (6) | |
C2B | 0.9147 (2) | 0.18401 (13) | 0.30644 (13) | 0.0419 (5) | |
C4B | 0.83605 (19) | 0.07198 (13) | 0.34354 (13) | 0.0412 (5) | |
C5B | 0.72803 (19) | 0.06269 (13) | 0.27621 (13) | 0.0414 (5) | |
C6B | 0.7245 (2) | 0.11616 (14) | 0.22588 (13) | 0.0465 (5) | |
H6D | 0.6579 | 0.1116 | 0.1799 | 0.056* | |
C7B | 0.6273 (2) | −0.00299 (16) | 0.26715 (15) | 0.0521 (6) | |
H7E | 0.5948 | 0.0124 | 0.3202 | 0.063* | |
H7F | 0.6621 | −0.0586 | 0.2623 | 0.063* | |
C8B | 0.5229 (2) | −0.01183 (14) | 0.18972 (14) | 0.0460 (5) | |
C9B | 0.5305 (2) | −0.06666 (14) | 0.10936 (15) | 0.0487 (5) | |
H9B | 0.6002 | −0.0972 | 0.1030 | 0.058* | |
C10B | 0.4346 (2) | −0.07654 (14) | 0.03770 (14) | 0.0490 (5) | |
C11B | 0.3312 (2) | −0.03009 (15) | 0.04715 (14) | 0.0490 (5) | |
C12B | 0.3243 (2) | 0.02495 (16) | 0.12817 (16) | 0.0523 (6) | |
C13B | 0.4205 (2) | 0.03424 (15) | 0.19955 (15) | 0.0512 (6) | |
H13B | 0.4158 | 0.0715 | 0.2538 | 0.061* | |
C14B | 0.5386 (3) | −0.17720 (19) | −0.0574 (2) | 0.0789 (9) | |
H14D | 0.5261 | −0.2113 | −0.1174 | 0.118* | |
H14E | 0.5527 | −0.2142 | −0.0198 | 0.118* | |
H14F | 0.6083 | −0.1375 | −0.0443 | 0.118* | |
C15B | 0.1335 (3) | −0.0844 (3) | −0.0284 (2) | 0.0997 (12) | |
H15D | 0.0732 | −0.0831 | −0.0790 | 0.150* | |
H15E | 0.1022 | −0.0597 | 0.0235 | 0.150* | |
H15F | 0.1523 | −0.1430 | −0.0317 | 0.150* | |
C16B | 0.2039 (3) | 0.1227 (2) | 0.2112 (2) | 0.0866 (9) | |
H16D | 0.1268 | 0.1486 | 0.2033 | 0.130* | |
H16E | 0.2688 | 0.1669 | 0.2336 | 0.130* | |
H16F | 0.2051 | 0.0895 | 0.2519 | 0.130* | |
O1A | 0.62326 (17) | 0.74670 (12) | 0.40443 (14) | 0.0777 (6) | |
O2A | 0.70294 (17) | 0.86409 (13) | 0.38799 (14) | 0.0801 (6) | |
C17A | 0.6216 (2) | 0.80623 (16) | 0.36924 (16) | 0.0543 (6) | |
C18A | 0.5111 (2) | 0.80566 (14) | 0.29826 (15) | 0.0463 (5) | |
C19A | 0.5070 (2) | 0.75344 (15) | 0.21295 (16) | 0.0539 (6) | |
C20A | 0.6046 (3) | 0.70157 (19) | 0.1898 (2) | 0.0798 (9) | |
H20A | 0.6728 | 0.7006 | 0.2328 | 0.096* | |
C21A | 0.5997 (5) | 0.6539 (2) | 0.1068 (3) | 0.1146 (14) | |
H21A | 0.6654 | 0.6215 | 0.0926 | 0.137* | |
C22A | 0.4952 (6) | 0.6527 (3) | 0.0407 (3) | 0.1171 (16) | |
H22A | 0.4923 | 0.6184 | −0.0162 | 0.141* | |
C23A | 0.4009 (4) | 0.7001 (2) | 0.0589 (2) | 0.0930 (11) | |
H23A | 0.3333 | 0.6985 | 0.0145 | 0.112* | |
C24A | 0.4025 (3) | 0.75323 (17) | 0.14612 (16) | 0.0615 (7) | |
C25A | 0.3079 (2) | 0.80447 (19) | 0.16664 (18) | 0.0652 (8) | |
H25A | 0.2404 | 0.8041 | 0.1226 | 0.078* | |
C26A | 0.3100 (2) | 0.85645 (17) | 0.25060 (18) | 0.0578 (6) | |
C27A | 0.2131 (3) | 0.9096 (2) | 0.2718 (3) | 0.0812 (9) | |
H27A | 0.1453 | 0.9096 | 0.2281 | 0.097* | |
C28A | 0.2171 (3) | 0.9592 (2) | 0.3528 (3) | 0.0983 (11) | |
H28A | 0.1519 | 0.9929 | 0.3651 | 0.118* | |
C29A | 0.3190 (3) | 0.9613 (2) | 0.4201 (2) | 0.0893 (10) | |
H29A | 0.3210 | 0.9970 | 0.4763 | 0.107* | |
C30A | 0.4140 (3) | 0.91195 (19) | 0.40396 (19) | 0.0683 (7) | |
H30A | 0.4802 | 0.9137 | 0.4494 | 0.082* | |
C31A | 0.4146 (2) | 0.85739 (15) | 0.31872 (15) | 0.0484 (5) | |
O1B | 0.8577 (2) | 0.53922 (14) | 0.42407 (18) | 0.1089 (9) | |
O2B | 0.90955 (18) | 0.44320 (15) | 0.31071 (13) | 0.0831 (6) | |
C17B | 0.8421 (2) | 0.47036 (17) | 0.36435 (18) | 0.0614 (7) | |
C18B | 0.7343 (2) | 0.41143 (14) | 0.35736 (15) | 0.0498 (5) | |
C19B | 0.7464 (2) | 0.35423 (15) | 0.40833 (15) | 0.0520 (6) | |
C20B | 0.8569 (2) | 0.35078 (17) | 0.46886 (16) | 0.0593 (6) | |
H20B | 0.9239 | 0.3877 | 0.4749 | 0.071* | |
C21B | 0.8655 (3) | 0.29486 (19) | 0.51724 (18) | 0.0722 (8) | |
H21B | 0.9383 | 0.2936 | 0.5561 | 0.087* | |
C22B | 0.7648 (4) | 0.2380 (2) | 0.5095 (2) | 0.0805 (9) | |
H22B | 0.7719 | 0.1998 | 0.5434 | 0.097* | |
C23B | 0.6587 (3) | 0.23892 (19) | 0.4533 (2) | 0.0779 (9) | |
H23B | 0.5935 | 0.2012 | 0.4491 | 0.094* | |
C24B | 0.6442 (3) | 0.29647 (16) | 0.40037 (17) | 0.0604 (7) | |
C25B | 0.5357 (3) | 0.29986 (18) | 0.34279 (19) | 0.0675 (7) | |
H25B | 0.4697 | 0.2625 | 0.3378 | 0.081* | |
C26B | 0.5224 (2) | 0.35731 (17) | 0.29236 (17) | 0.0599 (6) | |
C27B | 0.4101 (3) | 0.3622 (2) | 0.2337 (2) | 0.0750 (8) | |
H27B | 0.3433 | 0.3253 | 0.2280 | 0.090* | |
C28 | 0.3998 (3) | 0.4189 (2) | 0.1869 (2) | 0.0793 (9) | |
H28B | 0.3261 | 0.4208 | 0.1492 | 0.095* | |
C29B | 0.4982 (3) | 0.4751 (2) | 0.19389 (18) | 0.0740 (8) | |
H29B | 0.4893 | 0.5144 | 0.1611 | 0.089* | |
C30B | 0.6074 (3) | 0.47318 (18) | 0.24826 (17) | 0.0639 (7) | |
H30B | 0.6723 | 0.5110 | 0.2519 | 0.077* | |
C31B | 0.6235 (2) | 0.41439 (15) | 0.29936 (15) | 0.0533 (6) | |
O1W | 0.1841 (2) | 0.30063 (17) | 0.48211 (15) | 0.0914 (7) | |
H1W | 0.240 (3) | 0.277 (2) | 0.506 (2) | 0.137* | |
H2W | 0.167 (4) | 0.3487 (13) | 0.509 (3) | 0.137* | |
O2W | 0.8520 (3) | 0.30848 (16) | 0.16746 (17) | 0.1134 (9) | |
H4W | 0.866 (5) | 0.3533 (17) | 0.208 (2) | 0.170* | |
H3W | 0.869 (4) | 0.316 (3) | 0.1234 (18) | 0.170* | |
O3W | 0.9404 (2) | 0.88060 (17) | 0.47486 (18) | 0.1070 (9) | |
H5W | 0.956 (4) | 0.856 (2) | 0.513 (2) | 0.161* | |
H6W | 0.8695 (15) | 0.867 (3) | 0.448 (3) | 0.161* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0426 (10) | 0.0445 (10) | 0.0506 (10) | −0.0070 (8) | 0.0084 (8) | 0.0222 (8) |
N2A | 0.0421 (10) | 0.0580 (12) | 0.0606 (11) | −0.0089 (9) | 0.0034 (8) | 0.0294 (10) |
N3A | 0.0412 (10) | 0.0468 (10) | 0.0424 (9) | −0.0045 (8) | 0.0073 (7) | 0.0205 (8) |
N4A | 0.0519 (12) | 0.0712 (14) | 0.0659 (12) | −0.0196 (10) | −0.0028 (9) | 0.0421 (11) |
O10A | 0.0764 (12) | 0.0647 (11) | 0.0524 (10) | 0.0094 (9) | 0.0216 (8) | 0.0241 (8) |
O11A | 0.0697 (12) | 0.0681 (11) | 0.0837 (12) | 0.0042 (9) | 0.0052 (9) | 0.0498 (10) |
O12A | 0.0800 (14) | 0.0568 (11) | 0.1061 (16) | 0.0181 (10) | 0.0239 (12) | 0.0170 (11) |
C2A | 0.0425 (11) | 0.0382 (11) | 0.0392 (10) | −0.0007 (9) | 0.0107 (8) | 0.0123 (9) |
C4A | 0.0425 (12) | 0.0432 (11) | 0.0395 (10) | −0.0053 (9) | 0.0085 (9) | 0.0141 (9) |
C5A | 0.0430 (12) | 0.0470 (12) | 0.0375 (10) | −0.0032 (9) | 0.0092 (8) | 0.0154 (9) |
C6A | 0.0482 (13) | 0.0473 (12) | 0.0439 (11) | −0.0016 (10) | 0.0080 (9) | 0.0219 (10) |
C7A | 0.0493 (13) | 0.0749 (17) | 0.0519 (13) | −0.0128 (12) | 0.0012 (10) | 0.0329 (12) |
C8A | 0.0419 (12) | 0.0590 (14) | 0.0464 (12) | −0.0080 (11) | 0.0012 (9) | 0.0221 (11) |
C9A | 0.0447 (12) | 0.0490 (13) | 0.0525 (13) | 0.0013 (10) | 0.0054 (10) | 0.0227 (11) |
C10A | 0.0427 (12) | 0.0513 (13) | 0.0461 (12) | −0.0043 (10) | 0.0051 (9) | 0.0191 (10) |
C11A | 0.0442 (12) | 0.0486 (13) | 0.0584 (14) | −0.0026 (10) | 0.0012 (10) | 0.0251 (11) |
C12A | 0.0459 (13) | 0.0460 (13) | 0.0665 (15) | −0.0010 (10) | 0.0058 (11) | 0.0140 (12) |
C13A | 0.0499 (14) | 0.0631 (16) | 0.0502 (13) | −0.0067 (12) | 0.0096 (10) | 0.0094 (12) |
C14A | 0.0728 (18) | 0.0680 (18) | 0.0673 (16) | 0.0023 (15) | 0.0270 (14) | 0.0104 (14) |
C15 | 0.087 (3) | 0.159 (4) | 0.135 (3) | 0.007 (3) | −0.019 (2) | 0.100 (3) |
C16 | 0.090 (3) | 0.074 (2) | 0.156 (4) | 0.0070 (19) | 0.062 (3) | 0.000 (2) |
N1B | 0.0617 (12) | 0.0470 (10) | 0.0383 (9) | −0.0080 (9) | 0.0035 (8) | 0.0183 (8) |
N2B | 0.0535 (12) | 0.0550 (12) | 0.0551 (11) | −0.0111 (9) | 0.0092 (9) | 0.0194 (10) |
N3B | 0.0448 (10) | 0.0440 (10) | 0.0454 (10) | −0.0016 (8) | 0.0045 (8) | 0.0153 (8) |
N4B | 0.0547 (12) | 0.0566 (12) | 0.0568 (11) | −0.0090 (9) | −0.0077 (9) | 0.0310 (10) |
O10B | 0.0864 (13) | 0.0625 (11) | 0.0467 (9) | 0.0114 (10) | 0.0066 (9) | 0.0084 (8) |
O11B | 0.0624 (12) | 0.0848 (13) | 0.0586 (10) | −0.0007 (10) | −0.0111 (8) | 0.0257 (10) |
O12B | 0.0639 (12) | 0.0863 (14) | 0.0745 (12) | 0.0256 (11) | 0.0122 (9) | 0.0155 (11) |
C2B | 0.0470 (12) | 0.0409 (11) | 0.0371 (10) | −0.0030 (9) | 0.0116 (9) | 0.0077 (9) |
C4B | 0.0444 (12) | 0.0401 (11) | 0.0390 (10) | 0.0008 (9) | 0.0063 (9) | 0.0125 (9) |
C5B | 0.0463 (12) | 0.0409 (11) | 0.0350 (10) | −0.0014 (9) | 0.0029 (8) | 0.0111 (9) |
C6B | 0.0528 (13) | 0.0473 (12) | 0.0371 (11) | −0.0043 (10) | 0.0014 (9) | 0.0137 (10) |
C7B | 0.0500 (13) | 0.0568 (14) | 0.0509 (13) | −0.0083 (11) | −0.0006 (10) | 0.0252 (11) |
C8B | 0.0458 (12) | 0.0461 (12) | 0.0465 (12) | −0.0087 (10) | 0.0018 (9) | 0.0192 (10) |
C9B | 0.0469 (13) | 0.0454 (12) | 0.0560 (13) | 0.0004 (10) | 0.0072 (10) | 0.0204 (11) |
C10B | 0.0600 (14) | 0.0421 (12) | 0.0443 (12) | −0.0028 (11) | 0.0055 (10) | 0.0151 (10) |
C11B | 0.0479 (13) | 0.0502 (13) | 0.0466 (12) | −0.0028 (10) | −0.0016 (10) | 0.0180 (11) |
C12B | 0.0470 (13) | 0.0529 (14) | 0.0585 (14) | 0.0037 (11) | 0.0087 (10) | 0.0201 (12) |
C13B | 0.0558 (14) | 0.0493 (13) | 0.0458 (12) | −0.0060 (11) | 0.0074 (10) | 0.0110 (10) |
C14B | 0.113 (3) | 0.0614 (17) | 0.0711 (18) | 0.0244 (17) | 0.0368 (17) | 0.0200 (15) |
C15B | 0.063 (2) | 0.130 (3) | 0.082 (2) | −0.021 (2) | −0.0067 (16) | 0.005 (2) |
C16B | 0.091 (2) | 0.082 (2) | 0.094 (2) | 0.0281 (18) | 0.0366 (19) | 0.0240 (19) |
O1A | 0.0608 (11) | 0.0740 (12) | 0.1061 (15) | −0.0212 (9) | −0.0165 (10) | 0.0616 (12) |
O2A | 0.0570 (11) | 0.0780 (13) | 0.1078 (15) | −0.0317 (10) | −0.0242 (10) | 0.0591 (12) |
C17A | 0.0462 (13) | 0.0525 (14) | 0.0667 (15) | −0.0115 (11) | −0.0005 (11) | 0.0292 (12) |
C18A | 0.0424 (12) | 0.0432 (12) | 0.0554 (13) | −0.0126 (10) | 0.0013 (9) | 0.0236 (10) |
C19A | 0.0596 (15) | 0.0408 (12) | 0.0638 (15) | −0.0118 (11) | 0.0144 (12) | 0.0177 (11) |
C20A | 0.087 (2) | 0.0547 (17) | 0.105 (2) | −0.0015 (15) | 0.0351 (19) | 0.0228 (17) |
C21A | 0.158 (4) | 0.067 (2) | 0.129 (4) | 0.004 (2) | 0.080 (3) | 0.010 (2) |
C22A | 0.189 (5) | 0.075 (2) | 0.086 (3) | −0.036 (3) | 0.067 (3) | −0.007 (2) |
C23A | 0.127 (3) | 0.086 (2) | 0.0576 (18) | −0.050 (2) | 0.0131 (19) | 0.0097 (17) |
C24A | 0.0738 (18) | 0.0568 (15) | 0.0505 (14) | −0.0304 (14) | 0.0047 (12) | 0.0154 (12) |
C25A | 0.0536 (15) | 0.0759 (18) | 0.0659 (16) | −0.0278 (14) | −0.0120 (12) | 0.0369 (15) |
C26A | 0.0417 (13) | 0.0610 (15) | 0.0750 (17) | −0.0109 (11) | 0.0016 (11) | 0.0337 (14) |
C27A | 0.0459 (16) | 0.086 (2) | 0.121 (3) | −0.0007 (15) | 0.0115 (17) | 0.049 (2) |
C28A | 0.066 (2) | 0.087 (2) | 0.151 (4) | 0.0074 (18) | 0.044 (2) | 0.032 (3) |
C29A | 0.087 (2) | 0.080 (2) | 0.100 (2) | −0.0123 (18) | 0.048 (2) | 0.0022 (18) |
C30A | 0.0629 (17) | 0.0705 (18) | 0.0683 (17) | −0.0165 (14) | 0.0142 (13) | 0.0140 (14) |
C31A | 0.0428 (12) | 0.0471 (13) | 0.0569 (13) | −0.0122 (10) | 0.0054 (10) | 0.0208 (11) |
O1B | 0.0931 (17) | 0.0551 (12) | 0.144 (2) | −0.0197 (11) | −0.0086 (15) | −0.0055 (14) |
O2B | 0.0636 (12) | 0.1176 (18) | 0.0676 (12) | −0.0377 (12) | 0.0102 (10) | 0.0281 (12) |
C17B | 0.0567 (16) | 0.0540 (15) | 0.0673 (16) | −0.0122 (12) | −0.0028 (13) | 0.0179 (13) |
C18B | 0.0512 (13) | 0.0423 (12) | 0.0495 (12) | −0.0032 (10) | 0.0189 (10) | −0.0029 (10) |
C19B | 0.0543 (14) | 0.0480 (13) | 0.0507 (13) | 0.0007 (11) | 0.0252 (11) | −0.0010 (11) |
C20B | 0.0645 (16) | 0.0551 (15) | 0.0562 (14) | 0.0073 (12) | 0.0241 (12) | 0.0041 (12) |
C21B | 0.091 (2) | 0.0682 (18) | 0.0601 (16) | 0.0163 (16) | 0.0282 (15) | 0.0138 (14) |
C22B | 0.114 (3) | 0.0651 (19) | 0.0743 (19) | 0.0137 (19) | 0.0430 (19) | 0.0230 (16) |
C23B | 0.097 (2) | 0.0599 (17) | 0.083 (2) | −0.0063 (16) | 0.0438 (19) | 0.0130 (16) |
C24B | 0.0683 (17) | 0.0480 (14) | 0.0645 (15) | −0.0057 (12) | 0.0332 (13) | 0.0017 (12) |
C25B | 0.0593 (17) | 0.0595 (16) | 0.0766 (18) | −0.0156 (13) | 0.0302 (14) | −0.0034 (14) |
C26B | 0.0491 (14) | 0.0579 (15) | 0.0633 (15) | −0.0032 (12) | 0.0196 (12) | −0.0036 (12) |
C27B | 0.0506 (16) | 0.0735 (19) | 0.0830 (19) | −0.0062 (14) | 0.0142 (14) | −0.0065 (17) |
C28 | 0.0576 (18) | 0.083 (2) | 0.077 (2) | 0.0092 (16) | 0.0033 (14) | −0.0014 (17) |
C29B | 0.076 (2) | 0.0735 (19) | 0.0629 (16) | 0.0119 (16) | 0.0098 (14) | 0.0067 (14) |
C30B | 0.0637 (17) | 0.0614 (16) | 0.0612 (15) | 0.0013 (13) | 0.0134 (13) | 0.0081 (13) |
C31B | 0.0506 (14) | 0.0494 (13) | 0.0510 (13) | −0.0010 (11) | 0.0170 (11) | −0.0045 (11) |
O1W | 0.0707 (15) | 0.1076 (19) | 0.0831 (15) | 0.0086 (13) | −0.0105 (11) | 0.0244 (14) |
O2W | 0.205 (3) | 0.0729 (14) | 0.0905 (17) | 0.0040 (18) | 0.069 (2) | 0.0422 (13) |
O3W | 0.0789 (15) | 0.1150 (18) | 0.130 (2) | −0.0353 (14) | −0.0415 (14) | 0.0838 (17) |
N1A—C2A | 1.349 (2) | C13B—H13B | 0.9300 |
N1A—C6A | 1.362 (3) | C14B—H14D | 0.9600 |
N1A—H1A | 0.8600 | C14B—H14E | 0.9600 |
N2A—C2A | 1.318 (3) | C14B—H14F | 0.9600 |
N2A—H2A | 0.8600 | C15B—H15D | 0.9600 |
N2A—H2B | 0.8600 | C15B—H15E | 0.9600 |
N3A—C2A | 1.332 (2) | C15B—H15F | 0.9600 |
N3A—C4A | 1.340 (3) | C16B—H16D | 0.9600 |
N4A—C4A | 1.323 (3) | C16B—H16E | 0.9600 |
N4A—H4A | 0.8600 | C16B—H16F | 0.9600 |
N4A—H4B | 0.8600 | O1A—C17A | 1.249 (3) |
O10A—C10A | 1.364 (3) | O2A—C17A | 1.235 (3) |
O10A—C14A | 1.427 (3) | C17A—C18A | 1.512 (3) |
O11A—C11A | 1.377 (3) | C18A—C19A | 1.399 (3) |
O11A—C15 | 1.419 (4) | C18A—C31A | 1.400 (3) |
O12A—C12A | 1.365 (3) | C19A—C20A | 1.421 (4) |
O12A—C16 | 1.431 (4) | C19A—C24A | 1.428 (4) |
C4A—C5A | 1.436 (3) | C20A—C21A | 1.345 (5) |
C5A—C6A | 1.340 (3) | C20A—H20A | 0.9300 |
C5A—C7A | 1.513 (3) | C21A—C22A | 1.417 (6) |
C6A—H6C | 0.9300 | C21A—H21A | 0.9300 |
C7A—C8A | 1.506 (3) | C22A—C23A | 1.335 (6) |
C7A—H7C | 0.9700 | C22A—H22A | 0.9300 |
C7A—H7D | 0.9700 | C23A—C24A | 1.434 (4) |
C8A—C13A | 1.384 (3) | C23A—H23A | 0.9300 |
C8A—C9A | 1.386 (3) | C24A—C25A | 1.379 (4) |
C9A—C10A | 1.388 (3) | C25A—C26A | 1.384 (4) |
C9A—H9A | 0.9300 | C25A—H25A | 0.9300 |
C10A—C11A | 1.386 (3) | C26A—C27A | 1.419 (4) |
C11A—C12A | 1.382 (3) | C26A—C31A | 1.439 (3) |
C12A—C13A | 1.386 (3) | C27A—C28A | 1.329 (5) |
C13A—H13A | 0.9300 | C27A—H27A | 0.9300 |
C14A—H14A | 0.9600 | C28A—C29A | 1.407 (5) |
C14A—H14B | 0.9600 | C28A—H28A | 0.9300 |
C14A—H14C | 0.9600 | C29A—C30A | 1.352 (4) |
C15—H15A | 0.9600 | C29A—H29A | 0.9300 |
C15—H15B | 0.9600 | C30A—C31A | 1.421 (4) |
C15—H15C | 0.9600 | C30A—H30A | 0.9300 |
C16—H16A | 0.9600 | O1B—C17B | 1.243 (3) |
C16—H16B | 0.9600 | O2B—C17B | 1.252 (3) |
C16—H16C | 0.9600 | C17B—C18B | 1.503 (3) |
N1B—C2B | 1.348 (3) | C18B—C19B | 1.395 (3) |
N1B—C6B | 1.363 (3) | C18B—C31B | 1.409 (3) |
N1B—H1B | 0.8600 | C19B—C20B | 1.429 (4) |
N2B—C2B | 1.333 (3) | C19B—C24B | 1.438 (3) |
N2B—H2C | 0.8600 | C20B—C21B | 1.347 (4) |
N2B—H2D | 0.8600 | C20B—H20B | 0.9300 |
N3B—C2B | 1.319 (3) | C21B—C22B | 1.416 (4) |
N3B—C4B | 1.344 (3) | C21B—H21B | 0.9300 |
N4B—C4B | 1.318 (3) | C22B—C23B | 1.348 (5) |
N4B—H4C | 0.8600 | C22B—H22B | 0.9300 |
N4B—H4D | 0.8600 | C23B—C24B | 1.424 (4) |
O10B—C10B | 1.360 (3) | C23B—H23B | 0.9300 |
O10B—C14B | 1.420 (3) | C24B—C25B | 1.389 (4) |
O11B—C11B | 1.375 (3) | C25B—C26B | 1.391 (4) |
O11B—C15B | 1.402 (4) | C25B—H25B | 0.9300 |
O12B—C12B | 1.365 (3) | C26B—C31B | 1.425 (3) |
O12B—C16B | 1.405 (4) | C26B—C27B | 1.434 (4) |
C4B—C5B | 1.436 (3) | C27B—C28 | 1.337 (4) |
C5B—C6B | 1.342 (3) | C27B—H27B | 0.9300 |
C5B—C7B | 1.505 (3) | C28—C29B | 1.394 (4) |
C6B—H6D | 0.9300 | C28—H28B | 0.9300 |
C7B—C8B | 1.511 (3) | C29B—C30B | 1.363 (4) |
C7B—H7E | 0.9700 | C29B—H29B | 0.9300 |
C7B—H7F | 0.9700 | C30B—C31B | 1.418 (4) |
C8B—C13B | 1.377 (3) | C30B—H30B | 0.9300 |
C8B—C9B | 1.377 (3) | O1W—H1W | 0.820 (2) |
C9B—C10B | 1.390 (3) | O1W—H2W | 0.820 (2) |
C9B—H9B | 0.9300 | O2W—H4W | 0.820 (2) |
C10B—C11B | 1.390 (3) | O2W—H3W | 0.820 (2) |
C11B—C12B | 1.385 (3) | O3W—H5W | 0.820 (2) |
C12B—C13B | 1.390 (3) | O3W—H6W | 0.820 (2) |
C2A—N1A—C6A | 120.10 (17) | C8B—C13B—H13B | 120.1 |
C2A—N1A—H1A | 120.0 | C12B—C13B—H13B | 120.1 |
C6A—N1A—H1A | 120.0 | O10B—C14B—H14D | 109.5 |
C2A—N2A—H2A | 120.0 | O10B—C14B—H14E | 109.5 |
C2A—N2A—H2B | 120.0 | H14D—C14B—H14E | 109.5 |
H2A—N2A—H2B | 120.0 | O10B—C14B—H14F | 109.5 |
C2A—N3A—C4A | 118.37 (16) | H14D—C14B—H14F | 109.5 |
C4A—N4A—H4A | 120.0 | H14E—C14B—H14F | 109.5 |
C4A—N4A—H4B | 120.0 | O11B—C15B—H15D | 109.5 |
H4A—N4A—H4B | 120.0 | O11B—C15B—H15E | 109.5 |
C10A—O10A—C14A | 117.95 (18) | H15D—C15B—H15E | 109.5 |
C11A—O11A—C15 | 115.6 (2) | O11B—C15B—H15F | 109.5 |
C12A—O12A—C16 | 118.5 (3) | H15D—C15B—H15F | 109.5 |
N2A—C2A—N3A | 119.51 (17) | H15E—C15B—H15F | 109.5 |
N2A—C2A—N1A | 118.60 (18) | O12B—C16B—H16D | 109.5 |
N3A—C2A—N1A | 121.89 (18) | O12B—C16B—H16E | 109.5 |
N4A—C4A—N3A | 117.21 (18) | H16D—C16B—H16E | 109.5 |
N4A—C4A—C5A | 120.70 (19) | O12B—C16B—H16F | 109.5 |
N3A—C4A—C5A | 122.09 (18) | H16D—C16B—H16F | 109.5 |
C6A—C5A—C4A | 115.94 (18) | H16E—C16B—H16F | 109.5 |
C6A—C5A—C7A | 124.73 (18) | O2A—C17A—O1A | 124.9 (2) |
C4A—C5A—C7A | 119.30 (18) | O2A—C17A—C18A | 118.71 (19) |
C5A—C6A—N1A | 121.44 (18) | O1A—C17A—C18A | 116.37 (19) |
C5A—C6A—H6C | 119.3 | C19A—C18A—C31A | 121.0 (2) |
N1A—C6A—H6C | 119.3 | C19A—C18A—C17A | 119.4 (2) |
C8A—C7A—C5A | 115.62 (18) | C31A—C18A—C17A | 119.6 (2) |
C8A—C7A—H7C | 108.4 | C18A—C19A—C20A | 122.3 (3) |
C5A—C7A—H7C | 108.4 | C18A—C19A—C24A | 119.1 (2) |
C8A—C7A—H7D | 108.4 | C20A—C19A—C24A | 118.5 (3) |
C5A—C7A—H7D | 108.4 | C21A—C20A—C19A | 121.1 (4) |
H7C—C7A—H7D | 107.4 | C21A—C20A—H20A | 119.5 |
C13A—C8A—C9A | 119.9 (2) | C19A—C20A—H20A | 119.5 |
C13A—C8A—C7A | 120.3 (2) | C20A—C21A—C22A | 120.4 (4) |
C9A—C8A—C7A | 119.7 (2) | C20A—C21A—H21A | 119.8 |
C8A—C9A—C10A | 120.0 (2) | C22A—C21A—H21A | 119.8 |
C8A—C9A—H9A | 120.0 | C23A—C22A—C21A | 121.0 (4) |
C10A—C9A—H9A | 120.0 | C23A—C22A—H22A | 119.5 |
O10A—C10A—C11A | 115.16 (19) | C21A—C22A—H22A | 119.5 |
O10A—C10A—C9A | 125.0 (2) | C22A—C23A—C24A | 120.8 (4) |
C11A—C10A—C9A | 119.8 (2) | C22A—C23A—H23A | 119.6 |
O11A—C11A—C12A | 121.6 (2) | C24A—C23A—H23A | 119.6 |
O11A—C11A—C10A | 118.1 (2) | C25A—C24A—C19A | 119.6 (2) |
C12A—C11A—C10A | 120.1 (2) | C25A—C24A—C23A | 122.2 (3) |
O12A—C12A—C11A | 115.2 (2) | C19A—C24A—C23A | 118.2 (3) |
O12A—C12A—C13A | 124.9 (2) | C24A—C25A—C26A | 122.2 (2) |
C11A—C12A—C13A | 120.0 (2) | C24A—C25A—H25A | 118.9 |
C8A—C13A—C12A | 120.1 (2) | C26A—C25A—H25A | 118.9 |
C8A—C13A—H13A | 119.9 | C25A—C26A—C27A | 122.3 (3) |
C12A—C13A—H13A | 119.9 | C25A—C26A—C31A | 118.9 (2) |
O10A—C14A—H14A | 109.5 | C27A—C26A—C31A | 118.7 (3) |
O10A—C14A—H14B | 109.5 | C28A—C27A—C26A | 121.4 (3) |
H14A—C14A—H14B | 109.5 | C28A—C27A—H27A | 119.3 |
O10A—C14A—H14C | 109.5 | C26A—C27A—H27A | 119.3 |
H14A—C14A—H14C | 109.5 | C27A—C28A—C29A | 120.7 (3) |
H14B—C14A—H14C | 109.5 | C27A—C28A—H28A | 119.7 |
O11A—C15—H15A | 109.5 | C29A—C28A—H28A | 119.7 |
O11A—C15—H15B | 109.5 | C30A—C29A—C28A | 120.7 (3) |
H15A—C15—H15B | 109.5 | C30A—C29A—H29A | 119.7 |
O11A—C15—H15C | 109.5 | C28A—C29A—H29A | 119.7 |
H15A—C15—H15C | 109.5 | C29A—C30A—C31A | 121.2 (3) |
H15B—C15—H15C | 109.5 | C29A—C30A—H30A | 119.4 |
O12A—C16—H16A | 109.5 | C31A—C30A—H30A | 119.4 |
O12A—C16—H16B | 109.5 | C18A—C31A—C30A | 123.5 (2) |
H16A—C16—H16B | 109.5 | C18A—C31A—C26A | 119.1 (2) |
O12A—C16—H16C | 109.5 | C30A—C31A—C26A | 117.4 (2) |
H16A—C16—H16C | 109.5 | O1B—C17B—O2B | 126.7 (3) |
H16B—C16—H16C | 109.5 | O1B—C17B—C18B | 117.3 (3) |
C2B—N1B—C6B | 120.32 (17) | O2B—C17B—C18B | 116.0 (2) |
C2B—N1B—H1B | 119.8 | C19B—C18B—C31B | 121.3 (2) |
C6B—N1B—H1B | 119.8 | C19B—C18B—C17B | 119.0 (2) |
C2B—N2B—H2C | 120.0 | C31B—C18B—C17B | 119.7 (2) |
C2B—N2B—H2D | 120.0 | C18B—C19B—C20B | 122.6 (2) |
H2C—N2B—H2D | 120.0 | C18B—C19B—C24B | 119.1 (2) |
C2B—N3B—C4B | 118.65 (17) | C20B—C19B—C24B | 118.3 (2) |
C4B—N4B—H4C | 120.0 | C21B—C20B—C19B | 121.1 (3) |
C4B—N4B—H4D | 120.0 | C21B—C20B—H20B | 119.5 |
H4C—N4B—H4D | 120.0 | C19B—C20B—H20B | 119.5 |
C10B—O10B—C14B | 118.3 (2) | C20B—C21B—C22B | 120.7 (3) |
C11B—O11B—C15B | 114.8 (2) | C20B—C21B—H21B | 119.7 |
C12B—O12B—C16B | 118.3 (2) | C22B—C21B—H21B | 119.7 |
N3B—C2B—N2B | 119.52 (19) | C23B—C22B—C21B | 120.5 (3) |
N3B—C2B—N1B | 121.91 (19) | C23B—C22B—H22B | 119.8 |
N2B—C2B—N1B | 118.56 (19) | C21B—C22B—H22B | 119.8 |
N4B—C4B—N3B | 117.56 (18) | C22B—C23B—C24B | 121.4 (3) |
N4B—C4B—C5B | 120.38 (19) | C22B—C23B—H23B | 119.3 |
N3B—C4B—C5B | 122.07 (18) | C24B—C23B—H23B | 119.3 |
C6B—C5B—C4B | 115.80 (19) | C25B—C24B—C23B | 122.8 (3) |
C6B—C5B—C7B | 124.54 (18) | C25B—C24B—C19B | 119.0 (2) |
C4B—C5B—C7B | 119.65 (17) | C23B—C24B—C19B | 118.1 (3) |
C5B—C6B—N1B | 121.19 (19) | C24B—C25B—C26B | 122.2 (2) |
C5B—C6B—H6D | 119.4 | C24B—C25B—H25B | 118.9 |
N1B—C6B—H6D | 119.4 | C26B—C25B—H25B | 118.9 |
C5B—C7B—C8B | 114.87 (17) | C25B—C26B—C31B | 119.1 (2) |
C5B—C7B—H7E | 108.5 | C25B—C26B—C27B | 122.6 (3) |
C8B—C7B—H7E | 108.6 | C31B—C26B—C27B | 118.2 (3) |
C5B—C7B—H7F | 108.6 | C28—C27B—C26B | 121.2 (3) |
C8B—C7B—H7F | 108.5 | C28—C27B—H27B | 119.4 |
H7E—C7B—H7F | 107.5 | C26B—C27B—H27B | 119.4 |
C13B—C8B—C9B | 120.3 (2) | C27B—C28—C29B | 120.8 (3) |
C13B—C8B—C7B | 120.2 (2) | C27B—C28—H28B | 119.6 |
C9B—C8B—C7B | 119.5 (2) | C29B—C28—H28B | 119.6 |
C8B—C9B—C10B | 120.3 (2) | C30B—C29B—C28 | 120.7 (3) |
C8B—C9B—H9B | 119.8 | C30B—C29B—H29B | 119.7 |
C10B—C9B—H9B | 119.8 | C28—C29B—H29B | 119.7 |
O10B—C10B—C11B | 116.0 (2) | C29B—C30B—C31B | 120.9 (3) |
O10B—C10B—C9B | 124.3 (2) | C29B—C30B—H30B | 119.5 |
C11B—C10B—C9B | 119.7 (2) | C31B—C30B—H30B | 119.5 |
O11B—C11B—C12B | 121.3 (2) | C18B—C31B—C30B | 122.6 (2) |
O11B—C11B—C10B | 119.0 (2) | C18B—C31B—C26B | 119.2 (2) |
C12B—C11B—C10B | 119.6 (2) | C30B—C31B—C26B | 118.2 (2) |
O12B—C12B—C11B | 115.1 (2) | H1W—O1W—H2W | 119 (4) |
O12B—C12B—C13B | 124.6 (2) | H4W—O2W—H3W | 110 (5) |
C11B—C12B—C13B | 120.3 (2) | H5W—O3W—H6W | 109 (4) |
C8B—C13B—C12B | 119.8 (2) | ||
C4A—N3A—C2A—N2A | 179.8 (2) | C11B—C12B—C13B—C8B | −0.3 (3) |
C4A—N3A—C2A—N1A | 0.6 (3) | O2A—C17A—C18A—C19A | 97.1 (3) |
C6A—N1A—C2A—N2A | 177.6 (2) | O1A—C17A—C18A—C19A | −82.6 (3) |
C6A—N1A—C2A—N3A | −3.2 (3) | O2A—C17A—C18A—C31A | −82.8 (3) |
C2A—N3A—C4A—N4A | −176.6 (2) | O1A—C17A—C18A—C31A | 97.5 (3) |
C2A—N3A—C4A—C5A | 3.2 (3) | C31A—C18A—C19A—C20A | 178.7 (2) |
N4A—C4A—C5A—C6A | 175.4 (2) | C17A—C18A—C19A—C20A | −1.2 (3) |
N3A—C4A—C5A—C6A | −4.5 (3) | C31A—C18A—C19A—C24A | 0.0 (3) |
N4A—C4A—C5A—C7A | −2.8 (3) | C17A—C18A—C19A—C24A | −179.92 (19) |
N3A—C4A—C5A—C7A | 177.3 (2) | C18A—C19A—C20A—C21A | −178.1 (3) |
C4A—C5A—C6A—N1A | 1.9 (3) | C24A—C19A—C20A—C21A | 0.7 (4) |
C7A—C5A—C6A—N1A | −180.0 (2) | C19A—C20A—C21A—C22A | −1.6 (5) |
C2A—N1A—C6A—C5A | 1.7 (3) | C20A—C21A—C22A—C23A | 1.5 (6) |
C6A—C5A—C7A—C8A | 4.8 (4) | C21A—C22A—C23A—C24A | −0.3 (5) |
C4A—C5A—C7A—C8A | −177.2 (2) | C18A—C19A—C24A—C25A | 0.2 (3) |
C5A—C7A—C8A—C13A | −99.0 (3) | C20A—C19A—C24A—C25A | −178.6 (2) |
C5A—C7A—C8A—C9A | 83.5 (3) | C18A—C19A—C24A—C23A | 179.2 (2) |
C13A—C8A—C9A—C10A | −1.4 (3) | C20A—C19A—C24A—C23A | 0.4 (3) |
C7A—C8A—C9A—C10A | 176.2 (2) | C22A—C23A—C24A—C25A | 178.4 (3) |
C14A—O10A—C10A—C11A | 174.6 (2) | C22A—C23A—C24A—C19A | −0.6 (4) |
C14A—O10A—C10A—C9A | −5.9 (3) | C19A—C24A—C25A—C26A | −0.3 (3) |
C8A—C9A—C10A—O10A | −179.0 (2) | C23A—C24A—C25A—C26A | −179.3 (2) |
C8A—C9A—C10A—C11A | 0.4 (3) | C24A—C25A—C26A—C27A | 179.7 (2) |
C15—O11A—C11A—C12A | −72.9 (4) | C24A—C25A—C26A—C31A | 0.3 (3) |
C15—O11A—C11A—C10A | 112.1 (3) | C25A—C26A—C27A—C28A | −179.8 (3) |
O10A—C10A—C11A—O11A | −4.3 (3) | C31A—C26A—C27A—C28A | −0.4 (4) |
C9A—C10A—C11A—O11A | 176.3 (2) | C26A—C27A—C28A—C29A | 0.8 (5) |
O10A—C10A—C11A—C12A | −179.3 (2) | C27A—C28A—C29A—C30A | −1.0 (5) |
C9A—C10A—C11A—C12A | 1.2 (3) | C28A—C29A—C30A—C31A | 0.7 (5) |
C16—O12A—C12A—C11A | 178.4 (3) | C19A—C18A—C31A—C30A | −179.7 (2) |
C16—O12A—C12A—C13A | −2.8 (4) | C17A—C18A—C31A—C30A | 0.2 (3) |
O11A—C11A—C12A—O12A | 2.1 (3) | C19A—C18A—C31A—C26A | 0.0 (3) |
C10A—C11A—C12A—O12A | 177.0 (2) | C17A—C18A—C31A—C26A | 179.89 (19) |
O11A—C11A—C12A—C13A | −176.8 (2) | C29A—C30A—C31A—C18A | 179.4 (2) |
C10A—C11A—C12A—C13A | −1.9 (3) | C29A—C30A—C31A—C26A | −0.3 (4) |
C9A—C8A—C13A—C12A | 0.7 (3) | C25A—C26A—C31A—C18A | −0.1 (3) |
C7A—C8A—C13A—C12A | −176.8 (2) | C27A—C26A—C31A—C18A | −179.5 (2) |
O12A—C12A—C13A—C8A | −177.8 (2) | C25A—C26A—C31A—C30A | 179.6 (2) |
C11A—C12A—C13A—C8A | 0.9 (3) | C27A—C26A—C31A—C30A | 0.2 (3) |
C4B—N3B—C2B—N2B | 178.0 (2) | O1B—C17B—C18B—C19B | −85.0 (3) |
C4B—N3B—C2B—N1B | −2.5 (3) | O2B—C17B—C18B—C19B | 92.6 (3) |
C6B—N1B—C2B—N3B | 1.7 (3) | O1B—C17B—C18B—C31B | 95.5 (3) |
C6B—N1B—C2B—N2B | −178.8 (2) | O2B—C17B—C18B—C31B | −86.9 (3) |
C2B—N3B—C4B—N4B | −178.9 (2) | C31B—C18B—C19B—C20B | −178.9 (2) |
C2B—N3B—C4B—C5B | 1.0 (3) | C17B—C18B—C19B—C20B | 1.6 (3) |
N4B—C4B—C5B—C6B | −178.8 (2) | C31B—C18B—C19B—C24B | 0.9 (3) |
N3B—C4B—C5B—C6B | 1.4 (3) | C17B—C18B—C19B—C24B | −178.7 (2) |
N4B—C4B—C5B—C7B | 2.3 (3) | C18B—C19B—C20B—C21B | 179.8 (2) |
N3B—C4B—C5B—C7B | −177.5 (2) | C24B—C19B—C20B—C21B | 0.1 (3) |
C4B—C5B—C6B—N1B | −2.2 (3) | C19B—C20B—C21B—C22B | −0.2 (4) |
C7B—C5B—C6B—N1B | 176.6 (2) | C20B—C21B—C22B—C23B | 0.1 (4) |
C2B—N1B—C6B—C5B | 0.9 (3) | C21B—C22B—C23B—C24B | 0.0 (4) |
C6B—C5B—C7B—C8B | 5.8 (3) | C22B—C23B—C24B—C25B | −179.1 (3) |
C4B—C5B—C7B—C8B | −175.4 (2) | C22B—C23B—C24B—C19B | −0.1 (4) |
C5B—C7B—C8B—C13B | −93.9 (3) | C18B—C19B—C24B—C25B | −0.7 (3) |
C5B—C7B—C8B—C9B | 86.4 (3) | C20B—C19B—C24B—C25B | 179.1 (2) |
C13B—C8B—C9B—C10B | −0.6 (3) | C18B—C19B—C24B—C23B | −179.7 (2) |
C7B—C8B—C9B—C10B | 179.1 (2) | C20B—C19B—C24B—C23B | 0.0 (3) |
C14B—O10B—C10B—C11B | 177.7 (2) | C23B—C24B—C25B—C26B | 179.1 (2) |
C14B—O10B—C10B—C9B | −3.3 (3) | C19B—C24B—C25B—C26B | 0.0 (4) |
C8B—C9B—C10B—O10B | −178.4 (2) | C24B—C25B—C26B—C31B | 0.4 (4) |
C8B—C9B—C10B—C11B | 0.7 (3) | C24B—C25B—C26B—C27B | −179.1 (2) |
C15B—O11B—C11B—C12B | −75.8 (3) | C25B—C26B—C27B—C28 | 179.2 (3) |
C15B—O11B—C11B—C10B | 107.3 (3) | C31B—C26B—C27B—C28 | −0.3 (4) |
O10B—C10B—C11B—O11B | −4.5 (3) | C26B—C27B—C28—C29B | −0.1 (4) |
C9B—C10B—C11B—O11B | 176.4 (2) | C27B—C28—C29B—C30B | 0.4 (4) |
O10B—C10B—C11B—C12B | 178.5 (2) | C28—C29B—C30B—C31B | −0.4 (4) |
C9B—C10B—C11B—C12B | −0.6 (3) | C19B—C18B—C31B—C30B | 178.5 (2) |
C16B—O12B—C12B—C11B | 177.2 (2) | C17B—C18B—C31B—C30B | −2.0 (3) |
C16B—O12B—C12B—C13B | −4.3 (4) | C19B—C18B—C31B—C26B | −0.4 (3) |
O11B—C11B—C12B—O12B | 2.1 (3) | C17B—C18B—C31B—C26B | 179.1 (2) |
C10B—C11B—C12B—O12B | 179.0 (2) | C29B—C30B—C31B—C18B | −178.9 (2) |
O11B—C11B—C12B—C13B | −176.5 (2) | C29B—C30B—C31B—C26B | 0.0 (4) |
C10B—C11B—C12B—C13B | 0.4 (3) | C25B—C26B—C31B—C18B | −0.2 (3) |
C9B—C8B—C13B—C12B | 0.4 (3) | C27B—C26B—C31B—C18B | 179.3 (2) |
C7B—C8B—C13B—C12B | −179.3 (2) | C25B—C26B—C31B—C30B | −179.2 (2) |
O12B—C12B—C13B—C8B | −178.8 (2) | C27B—C26B—C31B—C30B | 0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1A | 0.86 | 1.93 | 2.743 (3) | 158 |
N1B—H1B···O2W | 0.86 | 1.95 | 2.776 (3) | 160 |
O1W—H1W···O1Ai | 0.82 (3) | 2.01 (3) | 2.799 (3) | 162 (3) |
N2A—H2A···N3Ai | 0.86 | 2.17 | 3.024 (2) | 174 |
N2A—H2B···O1A | 0.86 | 2.41 | 3.100 (3) | 138 |
N2A—H2B···O1Wi | 0.86 | 2.44 | 3.214 (3) | 150 |
N2B—H2C···O1Wii | 0.86 | 2.08 | 2.905 (3) | 159 |
N2B—H2D···O2W | 0.86 | 2.42 | 3.126 (3) | 140 |
O1W—H2W···O1Bi | 0.82 (3) | 1.89 (3) | 2.709 (4) | 175 (3) |
O2W—H3W···O10Aiii | 0.82 (4) | 2.28 (4) | 3.006 (3) | 148 (4) |
O2W—H3W···O11Aiii | 0.82 (4) | 2.50 (4) | 3.198 (3) | 144 (4) |
N4A—H4B···O2Biv | 0.86 | 2.05 | 2.875 (3) | 160 |
N4B—H4C···O3Wv | 0.86 | 2.20 | 2.943 (3) | 145 |
N4B—H4D···O2Avi | 0.86 | 2.16 | 2.986 (3) | 161 |
O2W—H4W···O2B | 0.82 (3) | 1.86 (3) | 2.676 (3) | 171 (3) |
O3W—H5W···N3Bv | 0.82 (3) | 2.22 (3) | 2.906 (3) | 142 (3) |
O3W—H6W···O2A | 0.82 (3) | 1.92 (3) | 2.722 (3) | 166 (5) |
C6B—H6D···O10Bvii | 0.93 | 2.35 | 3.205 (3) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+2, −y+1, −z+1; (vi) x, y−1, z; (vii) −x+1, −y, −z. |
C12H14ClN4+·C5HCl2O2S− | Z = 2 |
Mr = 445.74 | F(000) = 456 |
Triclinic, P1 | Dx = 1.520 Mg m−3 |
a = 9.3415 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2751 (6) Å | Cell parameters from 3007 reflections |
c = 11.3730 (8) Å | θ = 4.2–30.1° |
α = 63.919 (7)° | µ = 0.60 mm−1 |
β = 85.243 (5)° | T = 293 K |
γ = 83.689 (5)° | Prism, colorless |
V = 973.80 (12) Å3 | 0.40 × 0.40 × 0.15 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 4449 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3226 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −10→13 |
Tmin = 0.750, Tmax = 1.000 | l = −14→14 |
9378 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.5521P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4449 reflections | Δρmax = 0.80 e Å−3 |
245 parameters | Δρmin = −0.62 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.21115 (12) | 1.24181 (8) | −0.15984 (10) | 0.0874 (3) | |
N1 | 0.3566 (2) | 0.3597 (2) | 0.2323 (2) | 0.0483 (5) | |
H1 | 0.3320 | 0.2916 | 0.2154 | 0.058* | |
N2 | 0.4866 (2) | 0.1871 (2) | 0.4012 (2) | 0.0510 (6) | |
H2B | 0.5382 | 0.1608 | 0.4684 | 0.061* | |
H2A | 0.4658 | 0.1236 | 0.3766 | 0.061* | |
N3 | 0.4705 (2) | 0.4241 (2) | 0.3730 (2) | 0.0425 (5) | |
N4 | 0.4505 (3) | 0.6600 (2) | 0.3411 (2) | 0.0511 (6) | |
H4A | 0.4936 | 0.6321 | 0.4133 | 0.061* | |
H4B | 0.4236 | 0.7505 | 0.2965 | 0.061* | |
C2 | 0.4391 (3) | 0.3251 (3) | 0.3359 (2) | 0.0413 (5) | |
C4 | 0.4257 (3) | 0.5637 (3) | 0.2987 (2) | 0.0400 (5) | |
C5 | 0.3519 (3) | 0.6083 (3) | 0.1799 (2) | 0.0424 (5) | |
C6 | 0.3118 (3) | 0.5008 (3) | 0.1539 (3) | 0.0502 (6) | |
C7 | 0.2123 (4) | 0.5236 (3) | 0.0460 (3) | 0.0708 (10) | |
H7B | 0.1500 | 0.4445 | 0.0778 | 0.085* | |
H7A | 0.1517 | 0.6133 | 0.0248 | 0.085* | |
C8 | 0.2910 (5) | 0.5304 (5) | −0.0722 (4) | 0.0973 (13) | |
H8C | 0.2240 | 0.5431 | −0.1367 | 0.146* | |
H8A | 0.3509 | 0.4416 | −0.0519 | 0.146* | |
H8B | 0.3501 | 0.6108 | −0.1060 | 0.146* | |
C9 | 0.3159 (3) | 0.7659 (3) | 0.0940 (2) | 0.0424 (5) | |
C10 | 0.1991 (3) | 0.8414 (3) | 0.1257 (3) | 0.0523 (6) | |
H10 | 0.1413 | 0.7931 | 0.1999 | 0.063* | |
C11 | 0.1677 (3) | 0.9878 (3) | 0.0481 (3) | 0.0561 (7) | |
H11 | 0.0901 | 1.0387 | 0.0705 | 0.067* | |
C12 | 0.2525 (3) | 1.0575 (3) | −0.0627 (3) | 0.0534 (7) | |
C13 | 0.3672 (3) | 0.9858 (3) | −0.0977 (3) | 0.0560 (7) | |
H13 | 0.4224 | 1.0342 | −0.1737 | 0.067* | |
C14 | 0.4000 (3) | 0.8395 (3) | −0.0182 (3) | 0.0504 (6) | |
H14 | 0.4791 | 0.7901 | −0.0400 | 0.060* | |
S1 | −0.12948 (9) | −0.16484 (12) | 0.44482 (10) | 0.0755 (3) | |
Cl2 | −0.09672 (10) | 0.13237 (10) | 0.24752 (10) | 0.0799 (3) | |
Cl3 | −0.00862 (15) | −0.45308 (11) | 0.63792 (11) | 0.1030 (4) | |
O1 | 0.2246 (2) | 0.1452 (2) | 0.2355 (2) | 0.0627 (6) | |
O2 | 0.3728 (2) | −0.0447 (2) | 0.3554 (2) | 0.0553 (5) | |
C15 | −0.0179 (3) | −0.0300 (3) | 0.3540 (3) | 0.0536 (7) | |
C16 | 0.1232 (3) | −0.0732 (3) | 0.3801 (3) | 0.0448 (6) | |
C17 | 0.1415 (3) | −0.2201 (3) | 0.4775 (3) | 0.0525 (6) | |
H17 | 0.2305 | −0.2683 | 0.5082 | 0.063* | |
C18 | 0.0167 (4) | −0.2808 (4) | 0.5196 (3) | 0.0645 (8) | |
C19 | 0.2496 (3) | 0.0166 (3) | 0.3186 (3) | 0.0470 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1212 (8) | 0.0349 (4) | 0.0871 (7) | 0.0069 (4) | −0.0239 (6) | −0.0089 (4) |
N1 | 0.0672 (14) | 0.0323 (10) | 0.0461 (12) | −0.0060 (9) | −0.0185 (10) | −0.0144 (9) |
N2 | 0.0623 (13) | 0.0336 (10) | 0.0549 (14) | −0.0009 (9) | −0.0219 (11) | −0.0144 (10) |
N3 | 0.0498 (11) | 0.0363 (10) | 0.0412 (11) | −0.0040 (8) | −0.0121 (9) | −0.0147 (9) |
N4 | 0.0691 (14) | 0.0376 (11) | 0.0491 (13) | −0.0017 (10) | −0.0213 (11) | −0.0185 (10) |
C2 | 0.0453 (12) | 0.0339 (11) | 0.0421 (13) | −0.0053 (9) | −0.0070 (10) | −0.0129 (10) |
C4 | 0.0452 (12) | 0.0348 (11) | 0.0382 (13) | −0.0079 (9) | −0.0051 (10) | −0.0124 (10) |
C5 | 0.0539 (14) | 0.0329 (11) | 0.0373 (13) | −0.0061 (10) | −0.0088 (10) | −0.0107 (10) |
C6 | 0.0708 (17) | 0.0355 (12) | 0.0412 (14) | −0.0061 (12) | −0.0154 (12) | −0.0113 (11) |
C7 | 0.112 (3) | 0.0410 (15) | 0.0560 (19) | −0.0004 (16) | −0.0343 (18) | −0.0144 (14) |
C8 | 0.104 (3) | 0.107 (3) | 0.091 (3) | 0.014 (3) | −0.025 (2) | −0.054 (3) |
C9 | 0.0559 (14) | 0.0335 (12) | 0.0380 (13) | −0.0042 (10) | −0.0123 (11) | −0.0139 (10) |
C10 | 0.0652 (17) | 0.0480 (15) | 0.0401 (14) | −0.0023 (12) | −0.0054 (12) | −0.0158 (12) |
C11 | 0.0667 (17) | 0.0515 (15) | 0.0514 (17) | 0.0107 (13) | −0.0152 (14) | −0.0250 (14) |
C12 | 0.0734 (18) | 0.0335 (12) | 0.0527 (17) | −0.0025 (12) | −0.0218 (14) | −0.0152 (12) |
C13 | 0.0667 (17) | 0.0377 (13) | 0.0533 (17) | −0.0134 (12) | −0.0012 (13) | −0.0084 (12) |
C14 | 0.0559 (15) | 0.0387 (13) | 0.0517 (16) | −0.0026 (11) | −0.0039 (12) | −0.0151 (12) |
S1 | 0.0624 (5) | 0.0995 (7) | 0.0784 (6) | −0.0239 (5) | 0.0116 (4) | −0.0496 (6) |
Cl2 | 0.0761 (6) | 0.0808 (6) | 0.0842 (6) | 0.0264 (4) | −0.0292 (5) | −0.0403 (5) |
Cl3 | 0.1455 (10) | 0.0716 (6) | 0.0807 (7) | −0.0497 (6) | 0.0346 (7) | −0.0203 (5) |
O1 | 0.0803 (13) | 0.0369 (10) | 0.0644 (13) | −0.0122 (9) | −0.0298 (11) | −0.0097 (9) |
O2 | 0.0557 (11) | 0.0482 (10) | 0.0553 (12) | −0.0064 (8) | −0.0137 (9) | −0.0139 (9) |
C15 | 0.0612 (16) | 0.0568 (16) | 0.0516 (16) | −0.0012 (13) | −0.0065 (13) | −0.0316 (14) |
C16 | 0.0566 (14) | 0.0395 (12) | 0.0427 (14) | −0.0061 (11) | −0.0065 (11) | −0.0207 (11) |
C17 | 0.0665 (17) | 0.0426 (14) | 0.0475 (16) | −0.0095 (12) | −0.0007 (13) | −0.0178 (12) |
C18 | 0.083 (2) | 0.0579 (17) | 0.0558 (18) | −0.0221 (15) | 0.0138 (16) | −0.0271 (15) |
C19 | 0.0624 (16) | 0.0365 (12) | 0.0440 (14) | −0.0065 (11) | −0.0159 (12) | −0.0161 (11) |
Cl1—C12 | 1.740 (3) | C9—C10 | 1.384 (4) |
N1—C2 | 1.354 (3) | C9—C14 | 1.390 (4) |
N1—C6 | 1.365 (3) | C10—C11 | 1.381 (4) |
N1—H1 | 0.8600 | C10—H10 | 0.9300 |
N2—C2 | 1.323 (3) | C11—C12 | 1.377 (4) |
N2—H2B | 0.8600 | C11—H11 | 0.9300 |
N2—H2A | 0.8600 | C12—C13 | 1.365 (4) |
N3—C2 | 1.327 (3) | C13—C14 | 1.386 (4) |
N3—C4 | 1.345 (3) | C13—H13 | 0.9300 |
N4—C4 | 1.324 (3) | C14—H14 | 0.9300 |
N4—H4A | 0.8600 | S1—C18 | 1.718 (4) |
N4—H4B | 0.8600 | S1—C15 | 1.719 (3) |
C4—C5 | 1.433 (3) | Cl2—C15 | 1.701 (3) |
C5—C6 | 1.357 (3) | Cl3—C18 | 1.716 (3) |
C5—C9 | 1.494 (3) | O1—C19 | 1.251 (3) |
C6—C7 | 1.522 (4) | O2—C19 | 1.259 (3) |
C7—C8 | 1.456 (6) | C15—C16 | 1.358 (4) |
C7—H7B | 0.9700 | C16—C17 | 1.429 (4) |
C7—H7A | 0.9700 | C16—C19 | 1.506 (4) |
C8—H8C | 0.9600 | C17—C18 | 1.335 (4) |
C8—H8A | 0.9600 | C17—H17 | 0.9300 |
C8—H8B | 0.9600 | ||
C2—N1—C6 | 121.2 (2) | C10—C9—C14 | 118.9 (2) |
C2—N1—H1 | 119.4 | C10—C9—C5 | 120.5 (2) |
C6—N1—H1 | 119.4 | C14—C9—C5 | 120.6 (2) |
C2—N2—H2B | 120.0 | C11—C10—C9 | 120.6 (3) |
C2—N2—H2A | 120.0 | C11—C10—H10 | 119.7 |
H2B—N2—H2A | 120.0 | C9—C10—H10 | 119.7 |
C2—N3—C4 | 117.9 (2) | C12—C11—C10 | 119.1 (3) |
C4—N4—H4A | 120.0 | C12—C11—H11 | 120.4 |
C4—N4—H4B | 120.0 | C10—C11—H11 | 120.4 |
H4A—N4—H4B | 120.0 | C13—C12—C11 | 121.7 (2) |
N2—C2—N3 | 120.6 (2) | C13—C12—Cl1 | 119.6 (2) |
N2—C2—N1 | 117.4 (2) | C11—C12—Cl1 | 118.6 (2) |
N3—C2—N1 | 122.0 (2) | C12—C13—C14 | 118.9 (3) |
N4—C4—N3 | 117.1 (2) | C12—C13—H13 | 120.6 |
N4—C4—C5 | 120.6 (2) | C14—C13—H13 | 120.6 |
N3—C4—C5 | 122.3 (2) | C13—C14—C9 | 120.8 (3) |
C6—C5—C4 | 116.6 (2) | C13—C14—H14 | 119.6 |
C6—C5—C9 | 122.7 (2) | C9—C14—H14 | 119.6 |
C4—C5—C9 | 120.6 (2) | C18—S1—C15 | 90.36 (15) |
C5—C6—N1 | 119.3 (2) | C16—C15—Cl2 | 130.2 (2) |
C5—C6—C7 | 124.9 (2) | C16—C15—S1 | 112.6 (2) |
N1—C6—C7 | 115.7 (2) | Cl2—C15—S1 | 117.20 (17) |
C8—C7—C6 | 112.5 (3) | C15—C16—C17 | 111.4 (3) |
C8—C7—H7B | 109.1 | C15—C16—C19 | 126.8 (2) |
C6—C7—H7B | 109.1 | C17—C16—C19 | 121.8 (2) |
C8—C7—H7A | 109.1 | C18—C17—C16 | 112.6 (3) |
C6—C7—H7A | 109.1 | C18—C17—H17 | 123.7 |
H7B—C7—H7A | 107.8 | C16—C17—H17 | 123.7 |
C7—C8—H8C | 109.5 | C17—C18—Cl3 | 127.2 (3) |
C7—C8—H8A | 109.5 | C17—C18—S1 | 113.0 (3) |
H8C—C8—H8A | 109.5 | Cl3—C18—S1 | 119.8 (2) |
C7—C8—H8B | 109.5 | O1—C19—O2 | 125.1 (3) |
H8C—C8—H8B | 109.5 | O1—C19—C16 | 118.0 (2) |
H8A—C8—H8B | 109.5 | O2—C19—C16 | 116.9 (2) |
C4—N3—C2—N2 | 176.6 (2) | C9—C10—C11—C12 | 1.1 (4) |
C4—N3—C2—N1 | −4.4 (4) | C10—C11—C12—C13 | −0.2 (4) |
C6—N1—C2—N2 | −175.3 (3) | C10—C11—C12—Cl1 | 179.7 (2) |
C6—N1—C2—N3 | 5.7 (4) | C11—C12—C13—C14 | −1.1 (4) |
C2—N3—C4—N4 | 176.2 (2) | Cl1—C12—C13—C14 | 179.0 (2) |
C2—N3—C4—C5 | −2.7 (4) | C12—C13—C14—C9 | 1.4 (4) |
N4—C4—C5—C6 | −170.4 (3) | C10—C9—C14—C13 | −0.5 (4) |
N3—C4—C5—C6 | 8.5 (4) | C5—C9—C14—C13 | −179.7 (2) |
N4—C4—C5—C9 | 6.8 (4) | C18—S1—C15—C16 | 0.3 (2) |
N3—C4—C5—C9 | −174.4 (2) | C18—S1—C15—Cl2 | 179.96 (18) |
C4—C5—C6—N1 | −7.2 (4) | Cl2—C15—C16—C17 | 180.0 (2) |
C9—C5—C6—N1 | 175.8 (3) | S1—C15—C16—C17 | −0.4 (3) |
C4—C5—C6—C7 | 169.6 (3) | Cl2—C15—C16—C19 | 0.3 (4) |
C9—C5—C6—C7 | −7.4 (5) | S1—C15—C16—C19 | 179.9 (2) |
C2—N1—C6—C5 | 0.6 (4) | C15—C16—C17—C18 | 0.3 (3) |
C2—N1—C6—C7 | −176.5 (3) | C19—C16—C17—C18 | 180.0 (2) |
C5—C6—C7—C8 | 97.2 (4) | C16—C17—C18—Cl3 | −178.4 (2) |
N1—C6—C7—C8 | −85.9 (4) | C16—C17—C18—S1 | −0.1 (3) |
C6—C5—C9—C10 | 98.4 (3) | C15—S1—C18—C17 | −0.1 (3) |
C4—C5—C9—C10 | −78.5 (3) | C15—S1—C18—Cl3 | 178.4 (2) |
C6—C5—C9—C14 | −82.4 (4) | C15—C16—C19—O1 | 0.8 (4) |
C4—C5—C9—C14 | 100.7 (3) | C17—C16—C19—O1 | −178.9 (2) |
C14—C9—C10—C11 | −0.8 (4) | C15—C16—C19—O2 | −179.2 (3) |
C5—C9—C10—C11 | 178.4 (2) | C17—C16—C19—O2 | 1.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.82 | 2.627 (3) | 155 |
N2—H2A···O2 | 0.86 | 2.13 | 2.969 (3) | 165 |
N2—H2B···O2i | 0.86 | 2.02 | 2.855 (3) | 163 |
N4—H4A···N3ii | 0.86 | 2.28 | 3.107 (3) | 160 |
N4—H4B···O2iii | 0.86 | 2.46 | 3.113 (3) | 133 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z. |
C12H14ClN4+·C5H2BrO2S− | F(000) = 1840 |
Mr = 455.76 | Dx = 1.513 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 17.0836 (6) Å | Cell parameters from 3232 reflections |
b = 15.8893 (3) Å | θ = 4.0–74.6° |
c = 16.4764 (5) Å | µ = 5.17 mm−1 |
β = 116.538 (4)° | T = 293 K |
V = 4001.2 (2) Å3 | Prism, colorless |
Z = 8 | 0.25 × 0.15 × 0.10 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 3801 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3191 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.024 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 70.1°, θmin = 4.0° |
ω scans | h = −20→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −19→13 |
Tmin = 0.623, Tmax = 1.000 | l = −20→18 |
7903 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0842P)2 + 5.1068P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.160 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.97 e Å−3 |
3801 reflections | Δρmin = −0.84 e Å−3 |
283 parameters | Extinction correction: SHELXT (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
67 restraints | Extinction coefficient: 0.00072 (9) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.69998 (9) | 0.89606 (7) | 0.96608 (6) | 0.0831 (4) | |
N1 | 0.51122 (15) | 0.65646 (16) | 0.47653 (15) | 0.0445 (5) | |
H1 | 0.4633 | 0.6293 | 0.4466 | 0.053* | |
N2 | 0.54779 (19) | 0.62888 (19) | 0.36144 (17) | 0.0600 (7) | |
H2B | 0.5824 | 0.6329 | 0.3365 | 0.072* | |
H2A | 0.4990 | 0.6024 | 0.3342 | 0.072* | |
N3 | 0.64467 (15) | 0.70435 (15) | 0.48450 (14) | 0.0415 (5) | |
N4 | 0.73645 (16) | 0.78250 (17) | 0.60459 (16) | 0.0510 (6) | |
H4A | 0.7707 | 0.7856 | 0.5792 | 0.061* | |
H4B | 0.7506 | 0.8067 | 0.6559 | 0.061* | |
C2 | 0.56975 (19) | 0.66358 (18) | 0.44217 (17) | 0.0430 (6) | |
C4 | 0.66219 (17) | 0.74053 (16) | 0.56478 (17) | 0.0389 (5) | |
C5 | 0.60292 (17) | 0.73491 (17) | 0.60479 (17) | 0.0395 (6) | |
C6 | 0.52743 (17) | 0.69182 (18) | 0.55770 (17) | 0.0410 (6) | |
C7 | 0.45797 (19) | 0.6771 (2) | 0.5887 (2) | 0.0523 (7) | |
H7A | 0.4675 | 0.7153 | 0.6382 | 0.063* | |
H7B | 0.4011 | 0.6898 | 0.5392 | 0.063* | |
C8 | 0.4578 (4) | 0.5881 (3) | 0.6198 (4) | 0.0910 (14) | |
H8A | 0.4433 | 0.5504 | 0.5696 | 0.136* | |
H8B | 0.4153 | 0.5828 | 0.6427 | 0.136* | |
H8C | 0.5147 | 0.5744 | 0.6669 | 0.136* | |
C9 | 0.62628 (17) | 0.77495 (17) | 0.69469 (17) | 0.0398 (6) | |
C10 | 0.58558 (19) | 0.84802 (19) | 0.70127 (19) | 0.0461 (6) | |
H10 | 0.5426 | 0.8725 | 0.6491 | 0.055* | |
C11 | 0.6085 (2) | 0.88521 (19) | 0.7854 (2) | 0.0511 (7) | |
H11 | 0.5807 | 0.9342 | 0.7897 | 0.061* | |
C12 | 0.6720 (2) | 0.8491 (2) | 0.86128 (19) | 0.0524 (7) | |
C13 | 0.7135 (3) | 0.7772 (2) | 0.8570 (2) | 0.0619 (8) | |
H13 | 0.7568 | 0.7537 | 0.9095 | 0.074* | |
C14 | 0.6905 (2) | 0.7398 (2) | 0.7737 (2) | 0.0541 (7) | |
H14 | 0.7183 | 0.6905 | 0.7704 | 0.065* | |
S1A | 0.19412 (17) | 0.48790 (18) | 0.15394 (12) | 0.0550 (6) | 0.7687 (16) |
C17A | 0.1247 (5) | 0.4217 (4) | 0.1722 (5) | 0.0629 (18) | 0.7687 (16) |
C18A | 0.1514 (5) | 0.4039 (4) | 0.2609 (5) | 0.0631 (16) | 0.7687 (16) |
H18A | 0.1205 | 0.3698 | 0.2824 | 0.076* | 0.7687 (16) |
C19A | 0.2320 (10) | 0.4435 (10) | 0.3173 (10) | 0.058 (6) | 0.7687 (16) |
H19A | 0.2617 | 0.4368 | 0.3799 | 0.070* | 0.7687 (16) |
Br1A | 0.02332 (5) | 0.38313 (6) | 0.07422 (6) | 0.1213 (4) | 0.7687 (16) |
S1B | 0.2280 (8) | 0.4399 (8) | 0.3148 (7) | 0.045 (3) | 0.2313 (16) |
C18B | 0.1424 (15) | 0.4009 (14) | 0.2184 (12) | 0.059 (5) | 0.2313 (16) |
C17B | 0.1400 (12) | 0.4402 (14) | 0.1451 (12) | 0.055 (5) | 0.2313 (16) |
H17B | 0.0941 | 0.4348 | 0.0872 | 0.066* | 0.2313 (16) |
C19B | 0.215 (2) | 0.491 (3) | 0.1652 (14) | 0.051 (7) | 0.2313 (16) |
H19B | 0.2309 | 0.5157 | 0.1239 | 0.062* | 0.2313 (16) |
C16 | 0.26188 (19) | 0.49522 (18) | 0.2650 (2) | 0.0476 (7) | |
Br1B | 0.06494 (14) | 0.32211 (14) | 0.2266 (2) | 0.1011 (10) | 0.2313 (16) |
O1 | 0.38002 (16) | 0.55285 (17) | 0.38749 (15) | 0.0665 (7) | |
O2 | 0.35672 (16) | 0.59419 (17) | 0.24860 (16) | 0.0639 (6) | |
C15 | 0.33930 (19) | 0.55171 (19) | 0.30269 (19) | 0.0476 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1160 (9) | 0.0919 (7) | 0.0491 (5) | −0.0155 (6) | 0.0438 (5) | −0.0245 (4) |
N1 | 0.0357 (11) | 0.0603 (14) | 0.0370 (11) | −0.0122 (10) | 0.0158 (9) | −0.0077 (10) |
N2 | 0.0549 (15) | 0.0908 (19) | 0.0403 (13) | −0.0296 (14) | 0.0266 (12) | −0.0245 (13) |
N3 | 0.0381 (11) | 0.0558 (13) | 0.0330 (10) | −0.0090 (10) | 0.0179 (9) | −0.0074 (9) |
N4 | 0.0434 (13) | 0.0735 (16) | 0.0418 (12) | −0.0200 (12) | 0.0241 (11) | −0.0201 (11) |
C2 | 0.0429 (14) | 0.0545 (15) | 0.0329 (12) | −0.0075 (12) | 0.0180 (11) | −0.0053 (11) |
C4 | 0.0363 (13) | 0.0477 (13) | 0.0337 (12) | −0.0022 (10) | 0.0165 (10) | −0.0019 (10) |
C5 | 0.0360 (13) | 0.0495 (14) | 0.0353 (12) | −0.0006 (11) | 0.0179 (11) | −0.0034 (10) |
C6 | 0.0352 (13) | 0.0521 (14) | 0.0384 (13) | −0.0014 (11) | 0.0188 (11) | −0.0018 (11) |
C7 | 0.0371 (14) | 0.0728 (19) | 0.0515 (16) | −0.0087 (13) | 0.0238 (13) | −0.0104 (14) |
C8 | 0.102 (3) | 0.102 (3) | 0.096 (3) | −0.003 (3) | 0.068 (3) | 0.024 (3) |
C9 | 0.0360 (13) | 0.0509 (14) | 0.0362 (12) | −0.0060 (11) | 0.0194 (10) | −0.0053 (10) |
C10 | 0.0413 (14) | 0.0542 (15) | 0.0430 (14) | −0.0012 (12) | 0.0191 (12) | −0.0030 (11) |
C11 | 0.0518 (17) | 0.0519 (15) | 0.0582 (18) | −0.0092 (13) | 0.0322 (15) | −0.0145 (13) |
C12 | 0.0619 (19) | 0.0637 (18) | 0.0403 (14) | −0.0152 (15) | 0.0306 (14) | −0.0106 (13) |
C13 | 0.071 (2) | 0.074 (2) | 0.0357 (15) | 0.0057 (17) | 0.0185 (15) | 0.0004 (14) |
C14 | 0.0579 (18) | 0.0607 (17) | 0.0416 (15) | 0.0101 (14) | 0.0203 (14) | −0.0039 (13) |
S1A | 0.0517 (13) | 0.0643 (10) | 0.0391 (6) | −0.0057 (9) | 0.0114 (6) | −0.0156 (5) |
C17A | 0.050 (3) | 0.055 (4) | 0.075 (5) | −0.016 (3) | 0.020 (3) | −0.015 (3) |
C18A | 0.059 (3) | 0.050 (3) | 0.086 (4) | −0.010 (2) | 0.037 (4) | −0.007 (3) |
C19A | 0.040 (7) | 0.057 (9) | 0.071 (9) | 0.005 (6) | 0.020 (6) | −0.007 (6) |
Br1A | 0.0880 (5) | 0.1293 (7) | 0.1002 (6) | −0.0533 (5) | 0.0004 (4) | −0.0370 (4) |
S1B | 0.051 (6) | 0.047 (5) | 0.042 (4) | −0.008 (4) | 0.025 (4) | 0.000 (3) |
C18B | 0.056 (11) | 0.046 (9) | 0.088 (16) | −0.019 (8) | 0.043 (13) | −0.015 (12) |
C17B | 0.031 (7) | 0.064 (11) | 0.060 (10) | −0.017 (7) | 0.011 (6) | −0.024 (8) |
C19B | 0.036 (12) | 0.068 (12) | 0.045 (8) | −0.028 (9) | 0.014 (8) | −0.002 (9) |
C16 | 0.0388 (14) | 0.0487 (14) | 0.0502 (16) | −0.0009 (12) | 0.0154 (13) | −0.0105 (12) |
Br1B | 0.0666 (13) | 0.0859 (14) | 0.149 (2) | −0.0304 (10) | 0.0466 (13) | −0.0133 (13) |
O1 | 0.0555 (13) | 0.0873 (17) | 0.0455 (12) | −0.0266 (12) | 0.0124 (10) | −0.0044 (11) |
O2 | 0.0578 (14) | 0.0851 (16) | 0.0518 (12) | −0.0132 (12) | 0.0270 (11) | 0.0004 (11) |
C15 | 0.0373 (14) | 0.0580 (16) | 0.0442 (15) | −0.0027 (12) | 0.0153 (12) | −0.0057 (12) |
Cl1—C12 | 1.741 (3) | C11—C12 | 1.363 (5) |
N1—C2 | 1.356 (3) | C11—H11 | 0.9300 |
N1—C6 | 1.360 (3) | C12—C13 | 1.362 (5) |
N1—H1 | 0.8600 | C13—C14 | 1.383 (4) |
N2—C2 | 1.330 (3) | C13—H13 | 0.9300 |
N2—H2B | 0.8600 | C14—H14 | 0.9300 |
N2—H2A | 0.8600 | S1A—C16 | 1.676 (3) |
N3—C2 | 1.322 (4) | S1A—C17A | 1.709 (7) |
N3—C4 | 1.347 (3) | C17A—C18A | 1.352 (9) |
N4—C4 | 1.319 (3) | C17A—Br1A | 1.867 (7) |
N4—H4A | 0.8600 | C18A—C19A | 1.418 (16) |
N4—H4B | 0.8600 | C18A—H18A | 0.9300 |
C4—C5 | 1.437 (4) | C19A—C16 | 1.439 (13) |
C5—C6 | 1.356 (4) | C19A—H19A | 0.9300 |
C5—C9 | 1.493 (3) | S1B—C16 | 1.486 (9) |
C6—C7 | 1.505 (4) | S1B—C18B | 1.723 (17) |
C7—C8 | 1.504 (6) | C18B—C17B | 1.344 (18) |
C7—H7A | 0.9700 | C18B—Br1B | 1.870 (19) |
C7—H7B | 0.9700 | C17B—C19B | 1.42 (2) |
C8—H8A | 0.9600 | C17B—H17B | 0.9300 |
C8—H8B | 0.9600 | C19B—C16 | 1.47 (2) |
C8—H8C | 0.9600 | C19B—H19B | 0.9300 |
C9—C10 | 1.382 (4) | C16—C15 | 1.485 (4) |
C9—C14 | 1.391 (4) | Br1B—Br1Bi | 2.655 (5) |
C10—C11 | 1.392 (4) | O1—C15 | 1.252 (4) |
C10—H10 | 0.9300 | O2—C15 | 1.255 (4) |
C2—N1—C6 | 120.8 (2) | C12—C11—H11 | 120.4 |
C2—N1—H1 | 119.6 | C10—C11—H11 | 120.4 |
C6—N1—H1 | 119.6 | C13—C12—C11 | 121.7 (3) |
C2—N2—H2B | 120.0 | C13—C12—Cl1 | 119.5 (3) |
C2—N2—H2A | 120.0 | C11—C12—Cl1 | 118.9 (2) |
H2B—N2—H2A | 120.0 | C12—C13—C14 | 119.3 (3) |
C2—N3—C4 | 117.7 (2) | C12—C13—H13 | 120.4 |
C4—N4—H4A | 120.0 | C14—C13—H13 | 120.4 |
C4—N4—H4B | 120.0 | C13—C14—C9 | 120.7 (3) |
H4A—N4—H4B | 120.0 | C13—C14—H14 | 119.6 |
N3—C2—N2 | 120.3 (2) | C9—C14—H14 | 119.6 |
N3—C2—N1 | 122.8 (2) | C16—S1A—C17A | 92.6 (3) |
N2—C2—N1 | 116.9 (2) | C18A—C17A—S1A | 113.2 (5) |
N4—C4—N3 | 116.5 (2) | C18A—C17A—Br1A | 126.9 (6) |
N4—C4—C5 | 121.4 (2) | S1A—C17A—Br1A | 119.9 (4) |
N3—C4—C5 | 122.1 (2) | C17A—C18A—C19A | 112.0 (8) |
C6—C5—C4 | 117.0 (2) | C17A—C18A—H18A | 124.0 |
C6—C5—C9 | 123.2 (2) | C19A—C18A—H18A | 124.0 |
C4—C5—C9 | 119.9 (2) | C18A—C19A—C16 | 111.2 (10) |
C5—C6—N1 | 119.7 (2) | C18A—C19A—H19A | 124.4 |
C5—C6—C7 | 125.2 (2) | C16—C19A—H19A | 124.4 |
N1—C6—C7 | 115.1 (2) | C16—S1B—C18B | 94.8 (8) |
C8—C7—C6 | 112.5 (3) | C17B—C18B—S1B | 109.5 (13) |
C8—C7—H7A | 109.1 | C17B—C18B—Br1B | 129.6 (14) |
C6—C7—H7A | 109.1 | S1B—C18B—Br1B | 120.7 (11) |
C8—C7—H7B | 109.1 | C18B—C17B—C19B | 113.0 (16) |
C6—C7—H7B | 109.1 | C18B—C17B—H17B | 123.5 |
H7A—C7—H7B | 107.8 | C19B—C17B—H17B | 123.5 |
C7—C8—H8A | 109.5 | C17B—C19B—C16 | 105.9 (17) |
C7—C8—H8B | 109.5 | C17B—C19B—H19B | 127.0 |
H8A—C8—H8B | 109.5 | C16—C19B—H19B | 127.0 |
C7—C8—H8C | 109.5 | C19A—C16—C15 | 125.7 (7) |
H8A—C8—H8C | 109.5 | C19B—C16—C15 | 115.9 (11) |
H8B—C8—H8C | 109.5 | C19B—C16—S1B | 115.7 (10) |
C10—C9—C14 | 118.6 (2) | C15—C16—S1B | 128.4 (5) |
C10—C9—C5 | 121.0 (2) | C19A—C16—S1A | 110.9 (6) |
C14—C9—C5 | 120.4 (2) | C15—C16—S1A | 123.3 (3) |
C9—C10—C11 | 120.5 (3) | C18B—Br1B—Br1Bi | 137.0 (8) |
C9—C10—H10 | 119.8 | O1—C15—O2 | 126.5 (3) |
C11—C10—H10 | 119.8 | O1—C15—C16 | 115.0 (3) |
C12—C11—C10 | 119.3 (3) | O2—C15—C16 | 118.5 (3) |
C4—N3—C2—N2 | 177.9 (3) | C10—C9—C14—C13 | −0.3 (5) |
C4—N3—C2—N1 | −0.5 (4) | C5—C9—C14—C13 | 178.9 (3) |
C6—N1—C2—N3 | 0.1 (4) | C16—S1A—C17A—C18A | −0.4 (6) |
C6—N1—C2—N2 | −178.4 (3) | C16—S1A—C17A—Br1A | 178.8 (4) |
C2—N3—C4—N4 | −178.5 (3) | S1A—C17A—C18A—C19A | −1.2 (11) |
C2—N3—C4—C5 | 0.8 (4) | Br1A—C17A—C18A—C19A | 179.6 (8) |
N4—C4—C5—C6 | 178.7 (3) | C17A—C18A—C19A—C16 | 2.6 (14) |
N3—C4—C5—C6 | −0.5 (4) | C16—S1B—C18B—C17B | −4 (2) |
N4—C4—C5—C9 | −1.9 (4) | C16—S1B—C18B—Br1B | 179.9 (15) |
N3—C4—C5—C9 | 179.0 (2) | S1B—C18B—C17B—C19B | 10 (3) |
C4—C5—C6—N1 | 0.0 (4) | Br1B—C18B—C17B—C19B | −175 (3) |
C9—C5—C6—N1 | −179.4 (3) | C18B—C17B—C19B—C16 | −11 (4) |
C4—C5—C6—C7 | 178.6 (3) | C18A—C19A—C16—C15 | 174.0 (6) |
C9—C5—C6—C7 | −0.9 (5) | C18A—C19A—C16—S1A | −2.9 (12) |
C2—N1—C6—C5 | 0.2 (4) | C17B—C19B—C16—C15 | −174.7 (18) |
C2—N1—C6—C7 | −178.5 (3) | C17B—C19B—C16—S1B | 8 (3) |
C5—C6—C7—C8 | −105.8 (4) | C18B—S1B—C16—C19B | −2 (2) |
N1—C6—C7—C8 | 72.8 (4) | C18B—S1B—C16—C15 | −179.3 (10) |
C6—C5—C9—C10 | −74.2 (4) | C17A—S1A—C16—C19A | 1.9 (7) |
C4—C5—C9—C10 | 106.4 (3) | C17A—S1A—C16—C15 | −175.1 (4) |
C6—C5—C9—C14 | 106.6 (3) | C17B—C18B—Br1B—Br1Bi | −101 (3) |
C4—C5—C9—C14 | −72.8 (4) | S1B—C18B—Br1B—Br1Bi | 74 (2) |
C14—C9—C10—C11 | −0.2 (4) | C19A—C16—C15—O1 | −0.3 (9) |
C5—C9—C10—C11 | −179.4 (3) | C19B—C16—C15—O1 | −178 (2) |
C9—C10—C11—C12 | 0.5 (4) | S1B—C16—C15—O1 | −0.9 (8) |
C10—C11—C12—C13 | −0.2 (5) | S1A—C16—C15—O1 | 176.2 (3) |
C10—C11—C12—Cl1 | −179.9 (2) | C19A—C16—C15—O2 | −178.9 (8) |
C11—C12—C13—C14 | −0.2 (5) | C19B—C16—C15—O2 | 4 (2) |
Cl1—C12—C13—C14 | 179.5 (3) | S1B—C16—C15—O2 | −179.5 (7) |
C12—C13—C14—C9 | 0.5 (5) | S1A—C16—C15—O2 | −2.4 (4) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.79 | 2.636 (4) | 167 |
N2—H2A···O2 | 0.86 | 2.20 | 2.999 (4) | 154 |
N2—H2B···O2ii | 0.86 | 2.17 | 2.983 (4) | 156 |
N4—H4A···N3iii | 0.86 | 2.14 | 2.998 (4) | 179 |
N4—H4B···O2iv | 0.86 | 2.37 | 3.055 (4) | 137 |
Symmetry codes: (ii) −x+1, y, −z+1/2; (iii) −x+3/2, −y+3/2, −z+1; (iv) x+1/2, −y+3/2, z+1/2. |
C12H14ClN4+·C15H9O2−·C2H6O·H2O | F(000) = 1128 |
Mr = 535.03 | Dx = 1.257 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5195 (5) Å | Cell parameters from 3464 reflections |
b = 15.7842 (11) Å | θ = 3.5–26.3° |
c = 18.8336 (8) Å | µ = 0.17 mm−1 |
β = 92.293 (4)° | T = 293 K |
V = 2827.6 (3) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 6466 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3240 reflections with I > 2σ(I) |
Detector resolution: 10.4933 pixels mm-1 | Rint = 0.036 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −12→12 |
Tmin = 0.521, Tmax = 1.000 | k = −20→16 |
15577 measured reflections | l = −23→24 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.173 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.22 e Å−3 |
6466 reflections | Δρmin = −0.25 e Å−3 |
364 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
9 restraints | Extinction coefficient: 0.0039 (9) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | −0.13326 (11) | 0.14732 (7) | −0.10217 (5) | 0.1146 (4) | |
N1 | 0.20914 (19) | 0.50959 (13) | 0.16314 (8) | 0.0525 (5) | |
H1 | 0.1829 | 0.5280 | 0.2035 | 0.063* | |
N2 | 0.3892 (2) | 0.60564 (15) | 0.16893 (10) | 0.0695 (7) | |
H2B | 0.4619 | 0.6289 | 0.1514 | 0.083* | |
H2A | 0.3593 | 0.6229 | 0.2089 | 0.083* | |
N3 | 0.37026 (19) | 0.51682 (13) | 0.07231 (9) | 0.0540 (5) | |
N4 | 0.3470 (2) | 0.42930 (13) | −0.02286 (9) | 0.0607 (6) | |
H4A | 0.4212 | 0.4524 | −0.0388 | 0.073* | |
H4B | 0.3047 | 0.3897 | −0.0467 | 0.073* | |
C2 | 0.3238 (2) | 0.54371 (16) | 0.13453 (11) | 0.0518 (6) | |
C4 | 0.2979 (2) | 0.45465 (16) | 0.03846 (10) | 0.0492 (6) | |
C5 | 0.1740 (2) | 0.41696 (15) | 0.06574 (10) | 0.0464 (5) | |
C6 | 0.1338 (2) | 0.44692 (16) | 0.12996 (10) | 0.0497 (6) | |
C7 | 0.0096 (3) | 0.41584 (18) | 0.16882 (12) | 0.0640 (7) | |
H7A | −0.0473 | 0.3799 | 0.1374 | 0.077* | |
H7B | −0.0475 | 0.4640 | 0.1816 | 0.077* | |
C8 | 0.0508 (4) | 0.3667 (2) | 0.23539 (14) | 0.0986 (11) | |
H8A | 0.0998 | 0.4034 | 0.2686 | 0.148* | |
H8B | 0.1109 | 0.3204 | 0.2234 | 0.148* | |
H8C | −0.0322 | 0.3450 | 0.2564 | 0.148* | |
C9 | 0.0966 (2) | 0.35019 (16) | 0.02515 (10) | 0.0486 (6) | |
C10 | 0.0247 (3) | 0.36899 (18) | −0.03779 (13) | 0.0705 (8) | |
H10 | 0.0239 | 0.4245 | −0.0544 | 0.085* | |
C11 | −0.0467 (3) | 0.3069 (2) | −0.07691 (14) | 0.0793 (8) | |
H11 | −0.0954 | 0.3208 | −0.1191 | 0.095* | |
C12 | −0.0450 (3) | 0.2255 (2) | −0.05325 (14) | 0.0697 (8) | |
C13 | 0.0274 (3) | 0.2048 (2) | 0.00861 (15) | 0.0818 (9) | |
H13 | 0.0296 | 0.1489 | 0.0243 | 0.098* | |
C14 | 0.0969 (3) | 0.26707 (19) | 0.04751 (13) | 0.0685 (7) | |
H14 | 0.1449 | 0.2526 | 0.0897 | 0.082* | |
O1 | 0.09127 (19) | 0.59001 (14) | 0.27045 (9) | 0.0815 (6) | |
O2 | 0.2907 (2) | 0.65119 (15) | 0.30345 (10) | 0.0927 (7) | |
C15 | 0.1657 (3) | 0.63709 (18) | 0.31033 (12) | 0.0624 (7) | |
C16 | 0.0911 (3) | 0.68011 (18) | 0.37016 (11) | 0.0588 (7) | |
C17 | 0.0955 (3) | 0.64225 (18) | 0.43788 (12) | 0.0627 (7) | |
C18 | 0.1728 (3) | 0.5680 (2) | 0.45422 (14) | 0.0835 (9) | |
H18 | 0.2213 | 0.5412 | 0.4187 | 0.100* | |
C19 | 0.1778 (4) | 0.5350 (2) | 0.52095 (17) | 0.1066 (12) | |
H19 | 0.2299 | 0.4862 | 0.5306 | 0.128* | |
C20 | 0.1050 (5) | 0.5740 (3) | 0.57517 (18) | 0.1129 (13) | |
H20 | 0.1101 | 0.5512 | 0.6207 | 0.136* | |
C21 | 0.0288 (4) | 0.6432 (2) | 0.56222 (14) | 0.0899 (10) | |
H21 | −0.0204 | 0.6672 | 0.5989 | 0.108* | |
C22 | 0.0201 (3) | 0.6818 (2) | 0.49335 (12) | 0.0689 (8) | |
C23 | −0.0566 (3) | 0.7541 (2) | 0.47885 (13) | 0.0709 (8) | |
H23 | −0.1083 | 0.7779 | 0.5147 | 0.085* | |
C24 | −0.0595 (3) | 0.79269 (18) | 0.41272 (13) | 0.0634 (7) | |
C25 | −0.1360 (3) | 0.8682 (2) | 0.39747 (17) | 0.0798 (9) | |
H25 | −0.1893 | 0.8923 | 0.4326 | 0.096* | |
C26 | −0.1333 (3) | 0.9056 (2) | 0.33346 (19) | 0.0889 (9) | |
H26 | −0.1828 | 0.9556 | 0.3251 | 0.107* | |
C27 | −0.0553 (3) | 0.8693 (2) | 0.27877 (18) | 0.0897 (9) | |
H27 | −0.0536 | 0.8955 | 0.2346 | 0.108* | |
C28 | 0.0165 (3) | 0.7966 (2) | 0.29046 (14) | 0.0762 (8) | |
H28 | 0.0663 | 0.7734 | 0.2537 | 0.091* | |
C29 | 0.0184 (3) | 0.75462 (18) | 0.35686 (12) | 0.0594 (7) | |
O1W | −0.3231 (3) | 0.68555 (17) | 0.14092 (12) | 0.0941 (7) | |
H1W | −0.276 (4) | 0.666 (3) | 0.1754 (15) | 0.141* | |
H2W | −0.290 (4) | 0.7337 (12) | 0.140 (2) | 0.141* | |
O3 | −0.1936 (2) | 0.6008 (2) | 0.25040 (12) | 0.1119 (8) | |
H3 | −0.1088 | 0.5954 | 0.2586 | 0.168* | |
C30 | −0.2627 (5) | 0.6093 (4) | 0.31547 (17) | 0.160 (2) | |
H30A | −0.1949 | 0.5924 | 0.3526 | 0.192* | 0.443 (10) |
H30B | −0.2786 | 0.6694 | 0.3219 | 0.192* | 0.443 (10) |
H30C | −0.3149 | 0.5574 | 0.3229 | 0.192* | 0.557 (10) |
H30D | −0.1909 | 0.6128 | 0.3534 | 0.192* | 0.557 (10) |
C31A | −0.3908 (7) | 0.5686 (7) | 0.3311 (5) | 0.127 (5) | 0.443 (10) |
H31A | −0.4491 | 0.6071 | 0.3562 | 0.191* | 0.443 (10) |
H31B | −0.3712 | 0.5196 | 0.3602 | 0.191* | 0.443 (10) |
H31C | −0.4387 | 0.5514 | 0.2877 | 0.191* | 0.443 (10) |
C31B | −0.3465 (10) | 0.6708 (8) | 0.3229 (5) | 0.180 (6) | 0.557 (10) |
H31D | −0.3723 | 0.6741 | 0.3716 | 0.270* | 0.557 (10) |
H31E | −0.4292 | 0.6623 | 0.2929 | 0.270* | 0.557 (10) |
H31F | −0.3013 | 0.7225 | 0.3098 | 0.270* | 0.557 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1323 (8) | 0.1142 (8) | 0.0979 (6) | −0.0528 (6) | 0.0100 (5) | −0.0311 (5) |
N1 | 0.0507 (11) | 0.0695 (14) | 0.0382 (8) | −0.0002 (10) | 0.0144 (8) | −0.0086 (9) |
N2 | 0.0630 (13) | 0.0932 (18) | 0.0536 (11) | −0.0182 (12) | 0.0182 (10) | −0.0250 (11) |
N3 | 0.0537 (11) | 0.0672 (14) | 0.0420 (9) | −0.0026 (10) | 0.0135 (8) | −0.0073 (9) |
N4 | 0.0675 (13) | 0.0715 (15) | 0.0446 (9) | −0.0133 (11) | 0.0207 (9) | −0.0107 (10) |
C2 | 0.0489 (13) | 0.0648 (17) | 0.0421 (10) | 0.0034 (12) | 0.0081 (9) | −0.0042 (11) |
C4 | 0.0519 (13) | 0.0592 (16) | 0.0371 (10) | 0.0055 (12) | 0.0095 (9) | 0.0013 (10) |
C5 | 0.0484 (12) | 0.0537 (14) | 0.0373 (10) | 0.0048 (11) | 0.0059 (9) | 0.0040 (10) |
C6 | 0.0497 (13) | 0.0600 (16) | 0.0400 (10) | 0.0059 (12) | 0.0080 (9) | 0.0028 (11) |
C7 | 0.0623 (15) | 0.0766 (19) | 0.0549 (13) | −0.0059 (14) | 0.0238 (11) | −0.0100 (13) |
C8 | 0.123 (3) | 0.112 (3) | 0.0623 (16) | −0.022 (2) | 0.0307 (17) | 0.0156 (17) |
C9 | 0.0514 (13) | 0.0533 (16) | 0.0417 (11) | 0.0045 (11) | 0.0096 (9) | 0.0038 (11) |
C10 | 0.094 (2) | 0.0572 (18) | 0.0593 (15) | 0.0020 (15) | −0.0141 (13) | 0.0041 (13) |
C11 | 0.092 (2) | 0.084 (2) | 0.0606 (15) | 0.0015 (18) | −0.0209 (14) | −0.0046 (16) |
C12 | 0.0746 (18) | 0.073 (2) | 0.0627 (15) | −0.0137 (15) | 0.0120 (13) | −0.0077 (14) |
C13 | 0.111 (2) | 0.059 (2) | 0.0761 (18) | −0.0147 (18) | 0.0071 (17) | 0.0090 (16) |
C14 | 0.0836 (19) | 0.068 (2) | 0.0538 (13) | −0.0003 (15) | −0.0003 (12) | 0.0092 (14) |
O1 | 0.0658 (12) | 0.1105 (17) | 0.0692 (11) | −0.0030 (11) | 0.0159 (9) | −0.0410 (11) |
O2 | 0.0651 (12) | 0.137 (2) | 0.0774 (12) | −0.0075 (12) | 0.0225 (10) | −0.0464 (12) |
C15 | 0.0573 (16) | 0.080 (2) | 0.0501 (13) | 0.0047 (14) | 0.0100 (11) | −0.0135 (13) |
C16 | 0.0559 (14) | 0.0694 (18) | 0.0519 (12) | −0.0022 (13) | 0.0134 (10) | −0.0165 (12) |
C17 | 0.0690 (16) | 0.0671 (19) | 0.0529 (13) | −0.0061 (14) | 0.0135 (11) | −0.0135 (13) |
C18 | 0.094 (2) | 0.090 (2) | 0.0673 (17) | 0.0136 (19) | 0.0186 (15) | −0.0008 (16) |
C19 | 0.134 (3) | 0.107 (3) | 0.080 (2) | 0.023 (2) | 0.018 (2) | 0.010 (2) |
C20 | 0.148 (3) | 0.122 (3) | 0.0705 (19) | 0.012 (3) | 0.025 (2) | 0.014 (2) |
C21 | 0.109 (3) | 0.108 (3) | 0.0553 (16) | −0.002 (2) | 0.0266 (16) | −0.0072 (17) |
C22 | 0.0773 (18) | 0.076 (2) | 0.0545 (14) | −0.0079 (16) | 0.0194 (12) | −0.0163 (14) |
C23 | 0.0728 (17) | 0.082 (2) | 0.0594 (15) | −0.0074 (16) | 0.0246 (13) | −0.0239 (15) |
C24 | 0.0574 (15) | 0.0628 (18) | 0.0706 (15) | −0.0043 (14) | 0.0117 (12) | −0.0208 (14) |
C25 | 0.0693 (18) | 0.073 (2) | 0.098 (2) | 0.0008 (16) | 0.0175 (15) | −0.0196 (17) |
C26 | 0.075 (2) | 0.073 (2) | 0.118 (2) | 0.0093 (17) | 0.0090 (18) | −0.003 (2) |
C27 | 0.090 (2) | 0.088 (2) | 0.091 (2) | 0.007 (2) | 0.0105 (17) | 0.0118 (19) |
C28 | 0.0755 (19) | 0.091 (2) | 0.0635 (15) | 0.0072 (17) | 0.0147 (13) | −0.0042 (16) |
C29 | 0.0556 (14) | 0.0690 (18) | 0.0543 (13) | −0.0059 (13) | 0.0108 (11) | −0.0135 (13) |
O1W | 0.0987 (17) | 0.1035 (19) | 0.0807 (13) | −0.0149 (14) | 0.0115 (11) | −0.0223 (14) |
O3 | 0.0762 (14) | 0.157 (2) | 0.1023 (15) | 0.0081 (16) | 0.0031 (12) | −0.0314 (16) |
C30 | 0.104 (4) | 0.224 (6) | 0.153 (4) | 0.001 (4) | 0.019 (3) | 0.065 (4) |
C31A | 0.093 (7) | 0.161 (12) | 0.126 (7) | −0.003 (6) | −0.010 (5) | −0.009 (7) |
C31B | 0.106 (7) | 0.292 (17) | 0.141 (7) | 0.016 (8) | 0.000 (5) | −0.094 (9) |
Cl1—C12 | 1.737 (3) | C17—C22 | 1.434 (3) |
N1—C2 | 1.349 (3) | C18—C19 | 1.360 (4) |
N1—C6 | 1.359 (3) | C18—H18 | 0.9300 |
N1—H1 | 0.8600 | C19—C20 | 1.399 (5) |
N2—C2 | 1.315 (3) | C19—H19 | 0.9300 |
N2—H2B | 0.8600 | C20—C21 | 1.329 (5) |
N2—H2A | 0.8600 | C20—H20 | 0.9300 |
N3—C2 | 1.338 (2) | C21—C22 | 1.432 (4) |
N3—C4 | 1.345 (3) | C21—H21 | 0.9300 |
N4—C4 | 1.325 (2) | C22—C23 | 1.377 (4) |
N4—H4A | 0.8600 | C23—C24 | 1.386 (4) |
N4—H4B | 0.8600 | C23—H23 | 0.9300 |
C4—C5 | 1.434 (3) | C24—C25 | 1.420 (4) |
C5—C6 | 1.367 (3) | C24—C29 | 1.442 (3) |
C5—C9 | 1.481 (3) | C25—C26 | 1.344 (4) |
C6—C7 | 1.498 (3) | C25—H25 | 0.9300 |
C7—C8 | 1.513 (4) | C26—C27 | 1.415 (4) |
C7—H7A | 0.9700 | C26—H26 | 0.9300 |
C7—H7B | 0.9700 | C27—C28 | 1.348 (4) |
C8—H8A | 0.9600 | C27—H27 | 0.9300 |
C8—H8B | 0.9600 | C28—C29 | 1.415 (4) |
C8—H8C | 0.9600 | C28—H28 | 0.9300 |
C9—C10 | 1.378 (3) | O1W—H1W | 0.832 (10) |
C9—C14 | 1.378 (3) | O1W—H2W | 0.824 (10) |
C10—C11 | 1.388 (4) | O3—C30 | 1.4205 (10) |
C10—H10 | 0.9300 | O3—H3 | 0.8200 |
C11—C12 | 1.359 (4) | C30—C31B | 1.268 (9) |
C11—H11 | 0.9300 | C30—C31A | 1.4195 (10) |
C12—C13 | 1.369 (4) | C30—H30A | 0.9700 |
C13—C14 | 1.379 (4) | C30—H30B | 0.9700 |
C13—H13 | 0.9300 | C30—H30C | 0.9700 |
C14—H14 | 0.9300 | C30—H30D | 0.9700 |
O1—C15 | 1.255 (3) | C31A—H31A | 0.9600 |
O2—C15 | 1.222 (3) | C31A—H31B | 0.9600 |
C15—C16 | 1.516 (3) | C31A—H31C | 0.9600 |
C16—C29 | 1.382 (4) | C31B—H31D | 0.9600 |
C16—C17 | 1.408 (3) | C31B—H31E | 0.9600 |
C17—C18 | 1.411 (4) | C31B—H31F | 0.9600 |
C2—N1—C6 | 121.84 (17) | C19—C18—H18 | 119.4 |
C2—N1—H1 | 119.1 | C17—C18—H18 | 119.4 |
C6—N1—H1 | 119.1 | C18—C19—C20 | 120.4 (3) |
C2—N2—H2B | 120.0 | C18—C19—H19 | 119.8 |
C2—N2—H2A | 120.0 | C20—C19—H19 | 119.8 |
H2B—N2—H2A | 120.0 | C21—C20—C19 | 120.7 (3) |
C2—N3—C4 | 117.76 (18) | C21—C20—H20 | 119.7 |
C4—N4—H4A | 120.0 | C19—C20—H20 | 119.7 |
C4—N4—H4B | 120.0 | C20—C21—C22 | 121.8 (3) |
H4A—N4—H4B | 120.0 | C20—C21—H21 | 119.1 |
N2—C2—N3 | 120.1 (2) | C22—C21—H21 | 119.1 |
N2—C2—N1 | 118.34 (18) | C23—C22—C21 | 122.9 (2) |
N3—C2—N1 | 121.6 (2) | C23—C22—C17 | 119.6 (2) |
N4—C4—N3 | 116.21 (19) | C21—C22—C17 | 117.5 (3) |
N4—C4—C5 | 120.7 (2) | C22—C23—C24 | 122.3 (2) |
N3—C4—C5 | 123.08 (17) | C22—C23—H23 | 118.9 |
C6—C5—C4 | 115.9 (2) | C24—C23—H23 | 118.9 |
C6—C5—C9 | 123.49 (19) | C23—C24—C25 | 122.8 (2) |
C4—C5—C9 | 120.63 (17) | C23—C24—C29 | 118.7 (3) |
N1—C6—C5 | 119.82 (19) | C25—C24—C29 | 118.5 (3) |
N1—C6—C7 | 115.21 (17) | C26—C25—C24 | 121.5 (3) |
C5—C6—C7 | 125.0 (2) | C26—C25—H25 | 119.3 |
C6—C7—C8 | 112.9 (2) | C24—C25—H25 | 119.3 |
C6—C7—H7A | 109.0 | C25—C26—C27 | 120.3 (3) |
C8—C7—H7A | 109.0 | C25—C26—H26 | 119.8 |
C6—C7—H7B | 109.0 | C27—C26—H26 | 119.8 |
C8—C7—H7B | 109.0 | C28—C27—C26 | 120.2 (3) |
H7A—C7—H7B | 107.8 | C28—C27—H27 | 119.9 |
C7—C8—H8A | 109.5 | C26—C27—H27 | 119.9 |
C7—C8—H8B | 109.5 | C27—C28—C29 | 122.1 (3) |
H8A—C8—H8B | 109.5 | C27—C28—H28 | 118.9 |
C7—C8—H8C | 109.5 | C29—C28—H28 | 118.9 |
H8A—C8—H8C | 109.5 | C16—C29—C28 | 123.2 (2) |
H8B—C8—H8C | 109.5 | C16—C29—C24 | 119.4 (2) |
C10—C9—C14 | 117.6 (3) | C28—C29—C24 | 117.4 (3) |
C10—C9—C5 | 120.7 (2) | H1W—O1W—H2W | 99 (4) |
C14—C9—C5 | 121.7 (2) | C30—O3—H3 | 109.5 |
C9—C10—C11 | 121.4 (3) | C31B—C30—O3 | 118.8 (7) |
C9—C10—H10 | 119.3 | C31A—C30—O3 | 124.7 (6) |
C11—C10—H10 | 119.3 | C31A—C30—H30A | 106.2 |
C12—C11—C10 | 119.6 (3) | O3—C30—H30A | 106.2 |
C12—C11—H11 | 120.2 | C31A—C30—H30B | 106.2 |
C10—C11—H11 | 120.2 | O3—C30—H30B | 106.2 |
C11—C12—C13 | 120.3 (3) | H30A—C30—H30B | 106.4 |
C11—C12—Cl1 | 119.9 (2) | C31B—C30—H30C | 107.6 |
C13—C12—Cl1 | 119.8 (3) | O3—C30—H30C | 107.6 |
C12—C13—C14 | 119.7 (3) | C31B—C30—H30D | 107.6 |
C12—C13—H13 | 120.1 | O3—C30—H30D | 107.6 |
C14—C13—H13 | 120.1 | H30C—C30—H30D | 107.0 |
C9—C14—C13 | 121.4 (2) | C30—C31A—H31A | 109.5 |
C9—C14—H14 | 119.3 | C30—C31A—H31B | 109.5 |
C13—C14—H14 | 119.3 | H31A—C31A—H31B | 109.5 |
O2—C15—O1 | 124.9 (2) | C30—C31A—H31C | 109.5 |
O2—C15—C16 | 118.9 (2) | H31A—C31A—H31C | 109.5 |
O1—C15—C16 | 116.1 (2) | H31B—C31A—H31C | 109.5 |
C29—C16—C17 | 121.5 (2) | C30—C31B—H31D | 109.5 |
C29—C16—C15 | 119.5 (2) | C30—C31B—H31E | 109.5 |
C17—C16—C15 | 119.0 (2) | H31D—C31B—H31E | 109.5 |
C16—C17—C18 | 123.1 (2) | C30—C31B—H31F | 109.5 |
C16—C17—C22 | 118.5 (3) | H31D—C31B—H31F | 109.5 |
C18—C17—C22 | 118.3 (2) | H31E—C31B—H31F | 109.5 |
C19—C18—C17 | 121.2 (3) | ||
C4—N3—C2—N2 | −178.5 (2) | O1—C15—C16—C17 | 95.3 (3) |
C4—N3—C2—N1 | 0.6 (3) | C29—C16—C17—C18 | −177.5 (3) |
C6—N1—C2—N2 | 178.3 (2) | C15—C16—C17—C18 | 3.6 (4) |
C6—N1—C2—N3 | −0.8 (4) | C29—C16—C17—C22 | 1.2 (4) |
C2—N3—C4—N4 | −179.7 (2) | C15—C16—C17—C22 | −177.7 (2) |
C2—N3—C4—C5 | 0.5 (3) | C16—C17—C18—C19 | 177.9 (3) |
N4—C4—C5—C6 | 179.0 (2) | C22—C17—C18—C19 | −0.8 (5) |
N3—C4—C5—C6 | −1.2 (3) | C17—C18—C19—C20 | 0.4 (6) |
N4—C4—C5—C9 | −1.3 (3) | C18—C19—C20—C21 | 0.8 (6) |
N3—C4—C5—C9 | 178.4 (2) | C19—C20—C21—C22 | −1.4 (6) |
C2—N1—C6—C5 | 0.0 (3) | C20—C21—C22—C23 | −179.1 (3) |
C2—N1—C6—C7 | 179.9 (2) | C20—C21—C22—C17 | 0.9 (5) |
C4—C5—C6—N1 | 1.0 (3) | C16—C17—C22—C23 | 1.4 (4) |
C9—C5—C6—N1 | −178.7 (2) | C18—C17—C22—C23 | −179.8 (3) |
C4—C5—C6—C7 | −178.9 (2) | C16—C17—C22—C21 | −178.6 (3) |
C9—C5—C6—C7 | 1.4 (4) | C18—C17—C22—C21 | 0.2 (4) |
N1—C6—C7—C8 | −69.8 (3) | C21—C22—C23—C24 | 177.3 (3) |
C5—C6—C7—C8 | 110.1 (3) | C17—C22—C23—C24 | −2.7 (4) |
C6—C5—C9—C10 | 111.1 (3) | C22—C23—C24—C25 | −178.8 (3) |
C4—C5—C9—C10 | −68.6 (3) | C22—C23—C24—C29 | 1.3 (4) |
C6—C5—C9—C14 | −70.8 (3) | C23—C24—C25—C26 | 177.9 (3) |
C4—C5—C9—C14 | 109.6 (3) | C29—C24—C25—C26 | −2.2 (4) |
C14—C9—C10—C11 | 0.9 (4) | C24—C25—C26—C27 | 1.3 (5) |
C5—C9—C10—C11 | 179.1 (2) | C25—C26—C27—C28 | 0.2 (5) |
C9—C10—C11—C12 | −0.6 (4) | C26—C27—C28—C29 | −0.7 (5) |
C10—C11—C12—C13 | −0.3 (4) | C17—C16—C29—C28 | 177.2 (2) |
C10—C11—C12—Cl1 | −179.6 (2) | C15—C16—C29—C28 | −4.0 (4) |
C11—C12—C13—C14 | 1.0 (4) | C17—C16—C29—C24 | −2.6 (4) |
Cl1—C12—C13—C14 | −179.7 (2) | C15—C16—C29—C24 | 176.3 (2) |
C10—C9—C14—C13 | −0.2 (4) | C27—C28—C29—C16 | 180.0 (3) |
C5—C9—C14—C13 | −178.4 (2) | C27—C28—C29—C24 | −0.3 (4) |
C12—C13—C14—C9 | −0.7 (4) | C23—C24—C29—C16 | 1.3 (4) |
O2—C15—C16—C29 | 95.3 (3) | C25—C24—C29—C16 | −178.6 (2) |
O1—C15—C16—C29 | −83.6 (3) | C23—C24—C29—C28 | −178.4 (2) |
O2—C15—C16—C17 | −85.9 (3) | C25—C24—C29—C28 | 1.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.84 | 2.671 (3) | 161 |
O1W—H1W···O3 | 0.83 (3) | 1.89 (4) | 2.712 (3) | 168 (5) |
N2—H2A···O2 | 0.86 | 1.97 | 2.829 (3) | 175 |
N2—H2B···O1Wi | 0.86 | 2.25 | 3.080 (3) | 162 |
O3—H3···O1 | 0.82 | 1.91 | 2.728 (3) | 175 |
N4—H4A···N3ii | 0.86 | 2.16 | 3.006 (3) | 167 |
N4—H4B···O1Wiii | 0.86 | 2.15 | 2.871 (3) | 141 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z. |
2C12H14ClN4+·C10H6O6S22− | Z = 3 |
Mr = 785.71 | F(000) = 1224 |
Triclinic, P1 | Dx = 1.419 Mg m−3 |
a = 10.7421 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7053 (4) Å | Cell parameters from 8734 reflections |
c = 24.5947 (8) Å | θ = 3.3–29.5° |
α = 85.450 (3)° | µ = 0.35 mm−1 |
β = 87.699 (3)° | T = 293 K |
γ = 63.459 (3)° | Prism, colorless |
V = 2757.86 (16) Å3 | 0.60 × 0.40 × 0.15 mm |
Agilent SuperNova Dual Source diffractometer with an Atlas detector | 12628 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 9180 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −15→12 |
Tmin = 0.784, Tmax = 1.000 | l = −31→30 |
25967 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0484P)2 + 1.0461P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
12628 reflections | Δρmax = 0.45 e Å−3 |
706 parameters | Δρmin = −0.55 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.62574 (6) | 0.52251 (5) | 0.68473 (2) | 0.04102 (14) | |
S2A | 0.34145 (6) | 1.16218 (5) | 0.59755 (2) | 0.04086 (14) | |
S3B | 0.10394 (6) | 0.17877 (6) | 1.03066 (2) | 0.04328 (14) | |
Cl1B | 0.84874 (9) | 0.15386 (8) | 0.51678 (3) | 0.0740 (2) | |
Cl1A | 0.46575 (14) | 0.24419 (11) | 1.12142 (3) | 0.1209 (4) | |
Cl1C | 0.19389 (10) | 0.63173 (10) | 0.82549 (3) | 0.1029 (3) | |
O1A | 0.65040 (17) | 0.47013 (16) | 0.74113 (6) | 0.0504 (4) | |
O2A | 0.53248 (18) | 0.48564 (16) | 0.65817 (7) | 0.0522 (4) | |
O3A | 0.75295 (18) | 0.49597 (17) | 0.65505 (7) | 0.0578 (5) | |
O4A | 0.29612 (18) | 1.21432 (16) | 0.54254 (6) | 0.0516 (4) | |
O5A | 0.2269 (2) | 1.21172 (17) | 0.63613 (7) | 0.0664 (5) | |
O6A | 0.4612 (2) | 1.17545 (17) | 0.61325 (8) | 0.0643 (5) | |
O1B | 0.20227 (18) | 0.13773 (15) | 0.98567 (6) | 0.0512 (4) | |
O2B | −0.02714 (18) | 0.17879 (17) | 1.01878 (7) | 0.0564 (4) | |
O3B | 0.16230 (18) | 0.10850 (16) | 1.08227 (6) | 0.0512 (4) | |
N1B | 0.98632 (18) | −0.02742 (17) | 0.84240 (7) | 0.0389 (4) | |
H1B | 0.9564 | −0.0709 | 0.8643 | 0.047* | |
N2B | 1.0944 (2) | 0.0013 (2) | 0.91490 (7) | 0.0542 (6) | |
H2B1 | 1.1438 | 0.0329 | 0.9286 | 0.065* | |
H2B2 | 1.0640 | −0.0438 | 0.9354 | 0.065* | |
N3B | 1.11250 (19) | 0.09212 (18) | 0.83038 (7) | 0.0399 (4) | |
N4B | 1.1261 (2) | 0.18385 (19) | 0.74694 (7) | 0.0472 (5) | |
H4B1 | 1.1749 | 0.2147 | 0.7616 | 0.057* | |
H4B2 | 1.1076 | 0.1995 | 0.7127 | 0.057* | |
N1A | 0.49816 (18) | 0.35564 (17) | 0.79213 (7) | 0.0375 (4) | |
H1A | 0.5394 | 0.3931 | 0.7727 | 0.045* | |
N2A | 0.4269 (2) | 0.31398 (19) | 0.71286 (7) | 0.0471 (5) | |
H2A1 | 0.3831 | 0.2825 | 0.6954 | 0.057* | |
H2A2 | 0.4714 | 0.3509 | 0.6953 | 0.057* | |
N3A | 0.35752 (19) | 0.24875 (17) | 0.79456 (7) | 0.0381 (4) | |
N4A | 0.2965 (2) | 0.1852 (2) | 0.87733 (7) | 0.0500 (5) | |
H4A1 | 0.2502 | 0.1553 | 0.8604 | 0.060* | |
H4A2 | 0.2986 | 0.1787 | 0.9124 | 0.060* | |
N1C | −0.04610 (19) | 0.66654 (18) | 0.51177 (7) | 0.0420 (4) | |
H1C | −0.1276 | 0.7042 | 0.4975 | 0.050* | |
N2C | 0.0435 (2) | 0.60835 (19) | 0.42648 (8) | 0.0492 (5) | |
H2C1 | 0.1124 | 0.5695 | 0.4050 | 0.059* | |
H2C2 | −0.0394 | 0.6490 | 0.4136 | 0.059* | |
N3C | 0.1933 (2) | 0.54250 (18) | 0.49900 (8) | 0.0476 (5) | |
N4C | 0.3411 (2) | 0.4906 (2) | 0.57002 (9) | 0.0667 (6) | |
H4C1 | 0.4083 | 0.4527 | 0.5477 | 0.080* | |
H4C2 | 0.3582 | 0.4913 | 0.6038 | 0.080* | |
C2B | 1.0656 (2) | 0.0221 (2) | 0.86256 (8) | 0.0380 (5) | |
C4B | 1.0792 (2) | 0.1120 (2) | 0.77731 (8) | 0.0366 (5) | |
C5B | 0.9970 (2) | 0.0601 (2) | 0.75389 (8) | 0.0363 (4) | |
C6B | 0.9522 (2) | −0.0108 (2) | 0.78864 (8) | 0.0367 (5) | |
C7B | 0.8644 (2) | −0.0725 (2) | 0.77332 (9) | 0.0466 (6) | |
H7B1 | 0.9015 | −0.1586 | 0.7905 | 0.056* | |
H7B2 | 0.8693 | −0.0788 | 0.7341 | 0.056* | |
C8B | 0.7134 (3) | 0.0013 (3) | 0.79027 (13) | 0.0716 (8) | |
H8B1 | 0.7083 | 0.0117 | 0.8287 | 0.107* | |
H8B2 | 0.6627 | −0.0451 | 0.7820 | 0.107* | |
H8B3 | 0.6736 | 0.0839 | 0.7707 | 0.107* | |
C2A | 0.4261 (2) | 0.3057 (2) | 0.76685 (8) | 0.0349 (4) | |
C4A | 0.3644 (2) | 0.2411 (2) | 0.84953 (8) | 0.0357 (4) | |
C5A | 0.4415 (2) | 0.2904 (2) | 0.87810 (8) | 0.0347 (4) | |
C6A | 0.5075 (2) | 0.3484 (2) | 0.84749 (8) | 0.0357 (4) | |
C7A | 0.5999 (3) | 0.3981 (2) | 0.86949 (9) | 0.0494 (6) | |
H7A1 | 0.5712 | 0.4225 | 0.9064 | 0.059* | |
H7A2 | 0.5908 | 0.4738 | 0.8474 | 0.059* | |
C8A | 0.7498 (3) | 0.2987 (4) | 0.86955 (16) | 0.0926 (11) | |
H8A1 | 0.7596 | 0.2251 | 0.8926 | 0.139* | |
H8A2 | 0.8072 | 0.3337 | 0.8830 | 0.139* | |
H8A3 | 0.7780 | 0.2740 | 0.8331 | 0.139* | |
C2C | 0.0650 (2) | 0.6055 (2) | 0.47943 (9) | 0.0418 (5) | |
C4C | 0.2102 (2) | 0.5484 (2) | 0.55220 (10) | 0.0463 (5) | |
C5C | 0.0965 (2) | 0.6136 (2) | 0.58855 (9) | 0.0430 (5) | |
C6C | −0.0332 (2) | 0.6705 (2) | 0.56644 (9) | 0.0427 (5) | |
C7C | −0.1664 (2) | 0.7429 (2) | 0.59613 (10) | 0.0513 (6) | |
H7C1 | −0.1623 | 0.7001 | 0.6319 | 0.062* | |
H7C2 | −0.2424 | 0.7422 | 0.5764 | 0.062* | |
C8C | −0.1955 (3) | 0.8794 (3) | 0.60258 (14) | 0.0772 (9) | |
H8C1 | −0.1233 | 0.8807 | 0.6239 | 0.116* | |
H8C2 | −0.2835 | 0.9227 | 0.6207 | 0.116* | |
H8C3 | −0.1983 | 0.9218 | 0.5673 | 0.116* | |
C9B | 0.9608 (2) | 0.0855 (2) | 0.69486 (8) | 0.0386 (5) | |
C10B | 1.0616 (2) | 0.0317 (3) | 0.65523 (9) | 0.0478 (6) | |
H10B | 1.1533 | −0.0198 | 0.6656 | 0.057* | |
C11B | 1.0279 (3) | 0.0535 (3) | 0.60055 (9) | 0.0536 (6) | |
H11B | 1.0962 | 0.0174 | 0.5742 | 0.064* | |
C12B | 0.8927 (3) | 0.1288 (2) | 0.58561 (9) | 0.0487 (6) | |
C13B | 0.7909 (3) | 0.1844 (3) | 0.62333 (11) | 0.0595 (7) | |
H13B | 0.6995 | 0.2359 | 0.6125 | 0.071* | |
C14B | 0.8260 (3) | 0.1631 (2) | 0.67780 (10) | 0.0545 (6) | |
H14B | 0.7573 | 0.2019 | 0.7037 | 0.065* | |
C9A | 0.4470 (2) | 0.2781 (2) | 0.93868 (8) | 0.0364 (5) | |
C10A | 0.3705 (3) | 0.3831 (2) | 0.96847 (9) | 0.0466 (5) | |
H10A | 0.3139 | 0.4614 | 0.9504 | 0.056* | |
C11A | 0.3773 (3) | 0.3730 (3) | 1.02453 (10) | 0.0598 (7) | |
H11A | 0.3271 | 0.4442 | 1.0443 | 0.072* | |
C12A | 0.4585 (3) | 0.2576 (3) | 1.05061 (9) | 0.0619 (7) | |
C13A | 0.5331 (3) | 0.1512 (3) | 1.02239 (10) | 0.0613 (7) | |
H13A | 0.5865 | 0.0727 | 1.0409 | 0.074* | |
C14A | 0.5281 (3) | 0.1619 (2) | 0.96625 (9) | 0.0497 (6) | |
H14A | 0.5797 | 0.0905 | 0.9468 | 0.060* | |
C9C | 0.1210 (2) | 0.6166 (2) | 0.64731 (9) | 0.0479 (5) | |
C10C | 0.0767 (3) | 0.5517 (3) | 0.68785 (11) | 0.0655 (7) | |
H10C | 0.0318 | 0.5046 | 0.6779 | 0.079* | |
C11C | 0.0987 (4) | 0.5569 (3) | 0.74220 (12) | 0.0741 (9) | |
H11C | 0.0682 | 0.5140 | 0.7688 | 0.089* | |
C12C | 0.1655 (3) | 0.6251 (3) | 0.75684 (11) | 0.0660 (8) | |
C13C | 0.2107 (3) | 0.6894 (3) | 0.71842 (11) | 0.0663 (8) | |
H13C | 0.2561 | 0.7356 | 0.7289 | 0.080* | |
C14C | 0.1880 (3) | 0.6849 (3) | 0.66358 (10) | 0.0568 (6) | |
H14C | 0.2185 | 0.7287 | 0.6374 | 0.068* | |
C15A | 0.5414 (2) | 0.6924 (2) | 0.68794 (8) | 0.0369 (5) | |
C16A | 0.5287 (3) | 0.7405 (2) | 0.73792 (8) | 0.0457 (5) | |
H16A | 0.5571 | 0.6853 | 0.7692 | 0.055* | |
C17A | 0.4728 (3) | 0.8732 (2) | 0.74188 (9) | 0.0485 (6) | |
H17A | 0.4625 | 0.9054 | 0.7760 | 0.058* | |
C18A | 0.4336 (2) | 0.9551 (2) | 0.69691 (8) | 0.0424 (5) | |
H18A | 0.4007 | 1.0423 | 0.7004 | 0.051* | |
C19A | 0.4420 (2) | 0.9097 (2) | 0.64440 (8) | 0.0336 (4) | |
C20A | 0.3976 (2) | 0.9939 (2) | 0.59607 (8) | 0.0362 (5) | |
C21A | 0.4050 (2) | 0.9452 (2) | 0.54677 (8) | 0.0427 (5) | |
H21A | 0.3745 | 1.0005 | 0.5156 | 0.051* | |
C22A | 0.4584 (2) | 0.8124 (2) | 0.54241 (8) | 0.0439 (5) | |
H22A | 0.4634 | 0.7810 | 0.5084 | 0.053* | |
C23A | 0.5025 (2) | 0.7301 (2) | 0.58710 (8) | 0.0403 (5) | |
H23A | 0.5378 | 0.6426 | 0.5834 | 0.048* | |
C24A | 0.4957 (2) | 0.7754 (2) | 0.63970 (8) | 0.0335 (4) | |
C16B | 0.0849 (3) | 0.3710 (2) | 1.08970 (9) | 0.0515 (6) | |
H16B | 0.1176 | 0.3079 | 1.1181 | 0.062* | |
C15B | 0.0656 (2) | 0.3407 (2) | 1.03946 (9) | 0.0408 (5) | |
C24B | 0.0140 (2) | 0.4360 (2) | 0.99514 (8) | 0.0391 (5) | |
C23B | −0.0079 (3) | 0.4088 (2) | 0.94230 (9) | 0.0468 (5) | |
H23B | 0.0104 | 0.3257 | 0.9355 | 0.056* | |
C22B | −0.0553 (3) | 0.5026 (3) | 0.90141 (9) | 0.0562 (7) | |
H22B | −0.0685 | 0.4826 | 0.8669 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0451 (3) | 0.0384 (3) | 0.0428 (3) | −0.0227 (3) | 0.0064 (2) | 0.0014 (2) |
S2A | 0.0492 (3) | 0.0400 (3) | 0.0328 (3) | −0.0201 (3) | −0.0035 (2) | 0.0039 (2) |
S3B | 0.0577 (4) | 0.0406 (3) | 0.0401 (3) | −0.0307 (3) | 0.0072 (2) | 0.0010 (2) |
Cl1B | 0.1186 (6) | 0.0787 (5) | 0.0427 (3) | −0.0599 (5) | −0.0259 (4) | 0.0078 (3) |
Cl1A | 0.1973 (12) | 0.1175 (8) | 0.0310 (4) | −0.0546 (8) | −0.0176 (5) | 0.0010 (4) |
Cl1C | 0.0920 (6) | 0.1121 (7) | 0.0491 (4) | 0.0068 (5) | −0.0111 (4) | −0.0167 (4) |
O1A | 0.0604 (10) | 0.0493 (10) | 0.0467 (9) | −0.0311 (9) | −0.0001 (8) | 0.0092 (7) |
O2A | 0.0646 (11) | 0.0481 (10) | 0.0538 (10) | −0.0341 (9) | −0.0032 (8) | −0.0009 (8) |
O3A | 0.0507 (10) | 0.0515 (10) | 0.0671 (11) | −0.0211 (9) | 0.0202 (8) | −0.0021 (8) |
O4A | 0.0602 (10) | 0.0518 (10) | 0.0386 (8) | −0.0226 (9) | −0.0084 (7) | 0.0088 (7) |
O5A | 0.0811 (13) | 0.0469 (11) | 0.0497 (10) | −0.0123 (10) | 0.0238 (9) | 0.0023 (8) |
O6A | 0.0700 (12) | 0.0516 (11) | 0.0795 (13) | −0.0336 (10) | −0.0282 (10) | 0.0040 (9) |
O1B | 0.0681 (11) | 0.0470 (10) | 0.0440 (9) | −0.0318 (9) | 0.0153 (8) | −0.0037 (7) |
O2B | 0.0652 (11) | 0.0581 (11) | 0.0624 (11) | −0.0434 (10) | −0.0008 (9) | 0.0038 (8) |
O3B | 0.0663 (11) | 0.0469 (10) | 0.0444 (9) | −0.0310 (9) | 0.0059 (8) | 0.0065 (7) |
N1B | 0.0482 (11) | 0.0438 (11) | 0.0361 (9) | −0.0315 (9) | 0.0020 (8) | 0.0012 (8) |
N2B | 0.0796 (15) | 0.0766 (15) | 0.0342 (10) | −0.0610 (14) | −0.0052 (9) | 0.0065 (9) |
N3B | 0.0484 (11) | 0.0515 (11) | 0.0329 (9) | −0.0345 (10) | 0.0012 (8) | −0.0006 (8) |
N4B | 0.0661 (13) | 0.0639 (13) | 0.0323 (9) | −0.0482 (12) | −0.0010 (9) | 0.0017 (9) |
N1A | 0.0457 (10) | 0.0407 (10) | 0.0348 (9) | −0.0279 (9) | 0.0045 (8) | 0.0000 (7) |
N2A | 0.0654 (13) | 0.0574 (13) | 0.0314 (9) | −0.0393 (11) | 0.0014 (9) | −0.0006 (8) |
N3A | 0.0468 (10) | 0.0444 (11) | 0.0317 (9) | −0.0284 (9) | −0.0013 (7) | 0.0008 (7) |
N4A | 0.0679 (13) | 0.0750 (15) | 0.0331 (9) | −0.0559 (12) | −0.0002 (9) | 0.0015 (9) |
N1C | 0.0420 (10) | 0.0403 (11) | 0.0460 (10) | −0.0207 (9) | −0.0041 (8) | 0.0013 (8) |
N2C | 0.0500 (12) | 0.0487 (12) | 0.0457 (11) | −0.0188 (10) | −0.0016 (9) | −0.0042 (9) |
N3C | 0.0492 (12) | 0.0404 (11) | 0.0482 (11) | −0.0152 (9) | −0.0035 (9) | −0.0039 (9) |
N4C | 0.0504 (13) | 0.0689 (16) | 0.0605 (14) | −0.0065 (12) | −0.0116 (11) | −0.0107 (11) |
C2B | 0.0439 (12) | 0.0423 (12) | 0.0355 (11) | −0.0265 (10) | 0.0019 (9) | −0.0014 (9) |
C4B | 0.0403 (11) | 0.0410 (12) | 0.0332 (10) | −0.0228 (10) | 0.0056 (9) | −0.0032 (9) |
C5B | 0.0384 (11) | 0.0414 (12) | 0.0343 (10) | −0.0223 (10) | 0.0026 (8) | −0.0043 (9) |
C6B | 0.0369 (11) | 0.0390 (12) | 0.0387 (11) | −0.0207 (10) | 0.0017 (9) | −0.0055 (9) |
C7B | 0.0560 (14) | 0.0512 (14) | 0.0467 (13) | −0.0363 (12) | −0.0041 (11) | −0.0024 (11) |
C8B | 0.0514 (16) | 0.084 (2) | 0.090 (2) | −0.0393 (16) | −0.0081 (15) | −0.0035 (17) |
C2A | 0.0406 (11) | 0.0345 (11) | 0.0321 (10) | −0.0193 (10) | 0.0013 (8) | −0.0006 (8) |
C4A | 0.0398 (11) | 0.0404 (12) | 0.0319 (10) | −0.0227 (10) | 0.0000 (8) | −0.0001 (9) |
C5A | 0.0398 (11) | 0.0370 (12) | 0.0316 (10) | −0.0208 (10) | −0.0005 (8) | −0.0023 (8) |
C6A | 0.0394 (11) | 0.0361 (12) | 0.0355 (10) | −0.0203 (10) | 0.0007 (9) | −0.0030 (9) |
C7A | 0.0647 (16) | 0.0599 (16) | 0.0448 (13) | −0.0464 (14) | 0.0009 (11) | −0.0064 (11) |
C8A | 0.0581 (19) | 0.103 (3) | 0.132 (3) | −0.047 (2) | −0.0207 (19) | −0.017 (2) |
C2C | 0.0499 (13) | 0.0327 (12) | 0.0451 (12) | −0.0206 (10) | −0.0014 (10) | −0.0017 (9) |
C4C | 0.0489 (13) | 0.0352 (12) | 0.0510 (13) | −0.0154 (11) | −0.0048 (11) | −0.0001 (10) |
C5C | 0.0493 (13) | 0.0385 (12) | 0.0441 (12) | −0.0226 (11) | −0.0030 (10) | 0.0013 (10) |
C6C | 0.0503 (13) | 0.0399 (13) | 0.0465 (12) | −0.0286 (11) | 0.0009 (10) | 0.0007 (10) |
C7C | 0.0460 (13) | 0.0599 (16) | 0.0544 (14) | −0.0301 (13) | 0.0025 (11) | −0.0004 (12) |
C8C | 0.0612 (18) | 0.0614 (19) | 0.108 (3) | −0.0249 (16) | 0.0143 (17) | −0.0243 (17) |
C9B | 0.0470 (12) | 0.0420 (12) | 0.0350 (10) | −0.0272 (11) | −0.0002 (9) | −0.0033 (9) |
C10B | 0.0437 (13) | 0.0672 (17) | 0.0405 (12) | −0.0309 (13) | 0.0008 (10) | −0.0094 (11) |
C11B | 0.0602 (16) | 0.0772 (19) | 0.0382 (12) | −0.0426 (15) | 0.0048 (11) | −0.0139 (12) |
C12B | 0.0746 (17) | 0.0484 (14) | 0.0376 (12) | −0.0403 (14) | −0.0095 (12) | 0.0015 (10) |
C13B | 0.0596 (16) | 0.0515 (16) | 0.0555 (15) | −0.0137 (13) | −0.0145 (13) | 0.0010 (12) |
C14B | 0.0540 (15) | 0.0517 (15) | 0.0454 (13) | −0.0121 (12) | −0.0007 (11) | −0.0058 (11) |
C9A | 0.0415 (11) | 0.0443 (13) | 0.0310 (10) | −0.0261 (10) | −0.0013 (9) | −0.0016 (9) |
C10A | 0.0522 (14) | 0.0451 (14) | 0.0399 (12) | −0.0195 (11) | −0.0017 (10) | −0.0009 (10) |
C11A | 0.0814 (19) | 0.0571 (17) | 0.0391 (13) | −0.0282 (15) | 0.0045 (13) | −0.0120 (12) |
C12A | 0.085 (2) | 0.0704 (19) | 0.0306 (11) | −0.0353 (17) | −0.0076 (12) | −0.0010 (12) |
C13A | 0.0787 (19) | 0.0542 (17) | 0.0433 (13) | −0.0233 (15) | −0.0153 (13) | 0.0078 (12) |
C14A | 0.0590 (15) | 0.0418 (14) | 0.0422 (12) | −0.0169 (12) | −0.0033 (11) | −0.0032 (10) |
C9C | 0.0484 (13) | 0.0460 (14) | 0.0455 (13) | −0.0179 (11) | −0.0029 (10) | 0.0001 (10) |
C10C | 0.085 (2) | 0.0578 (17) | 0.0554 (16) | −0.0349 (16) | 0.0005 (14) | 0.0062 (13) |
C11C | 0.089 (2) | 0.0633 (19) | 0.0528 (16) | −0.0211 (18) | 0.0058 (15) | 0.0084 (14) |
C12C | 0.0522 (16) | 0.0669 (19) | 0.0463 (14) | 0.0033 (14) | −0.0039 (12) | −0.0066 (13) |
C13C | 0.0468 (15) | 0.089 (2) | 0.0589 (17) | −0.0234 (15) | −0.0018 (13) | −0.0218 (15) |
C14C | 0.0484 (14) | 0.0738 (19) | 0.0512 (14) | −0.0295 (14) | 0.0022 (11) | −0.0075 (13) |
C15A | 0.0420 (11) | 0.0407 (12) | 0.0339 (10) | −0.0241 (10) | 0.0023 (9) | −0.0003 (9) |
C16A | 0.0635 (15) | 0.0489 (14) | 0.0302 (10) | −0.0308 (12) | −0.0026 (10) | 0.0035 (9) |
C17A | 0.0715 (16) | 0.0520 (15) | 0.0277 (10) | −0.0319 (13) | −0.0018 (10) | −0.0056 (10) |
C18A | 0.0558 (14) | 0.0394 (13) | 0.0346 (11) | −0.0231 (11) | −0.0006 (10) | −0.0047 (9) |
C19A | 0.0339 (10) | 0.0414 (12) | 0.0294 (10) | −0.0205 (9) | 0.0014 (8) | −0.0013 (8) |
C20A | 0.0377 (11) | 0.0432 (12) | 0.0310 (10) | −0.0211 (10) | 0.0004 (8) | −0.0009 (9) |
C21A | 0.0498 (13) | 0.0527 (14) | 0.0294 (10) | −0.0265 (12) | −0.0040 (9) | 0.0012 (9) |
C22A | 0.0548 (14) | 0.0575 (15) | 0.0273 (10) | −0.0312 (12) | 0.0019 (9) | −0.0090 (10) |
C23A | 0.0456 (12) | 0.0456 (13) | 0.0360 (11) | −0.0256 (11) | 0.0056 (9) | −0.0068 (9) |
C24A | 0.0329 (10) | 0.0419 (12) | 0.0311 (10) | −0.0220 (9) | 0.0022 (8) | −0.0010 (8) |
C16B | 0.0754 (17) | 0.0503 (15) | 0.0355 (11) | −0.0348 (14) | −0.0032 (11) | 0.0041 (10) |
C15B | 0.0503 (13) | 0.0403 (12) | 0.0387 (11) | −0.0271 (11) | 0.0046 (9) | −0.0002 (9) |
C24B | 0.0469 (12) | 0.0416 (12) | 0.0365 (11) | −0.0269 (10) | 0.0036 (9) | −0.0019 (9) |
C23B | 0.0620 (15) | 0.0434 (13) | 0.0425 (12) | −0.0300 (12) | −0.0021 (11) | −0.0038 (10) |
C22B | 0.088 (2) | 0.0547 (16) | 0.0349 (12) | −0.0396 (15) | −0.0046 (12) | −0.0042 (11) |
S1A—O3A | 1.4399 (16) | C4C—C5C | 1.435 (3) |
S1A—O2A | 1.4492 (17) | C5C—C6C | 1.362 (3) |
S1A—O1A | 1.4560 (15) | C5C—C9C | 1.485 (3) |
S1A—C15A | 1.786 (2) | C6C—C7C | 1.493 (3) |
S2A—O6A | 1.4339 (17) | C7C—C8C | 1.505 (4) |
S2A—O4A | 1.4479 (15) | C7C—H7C1 | 0.9700 |
S2A—O5A | 1.4511 (18) | C7C—H7C2 | 0.9700 |
S2A—C20A | 1.787 (2) | C8C—H8C1 | 0.9600 |
S3B—O2B | 1.4494 (17) | C8C—H8C2 | 0.9600 |
S3B—O1B | 1.4518 (16) | C8C—H8C3 | 0.9600 |
S3B—O3B | 1.4554 (16) | C9B—C14B | 1.382 (3) |
S3B—C15B | 1.780 (2) | C9B—C10B | 1.386 (3) |
Cl1B—C12B | 1.743 (2) | C10B—C11B | 1.381 (3) |
Cl1A—C12A | 1.738 (2) | C10B—H10B | 0.9300 |
Cl1C—C12C | 1.741 (3) | C11B—C12B | 1.367 (4) |
N1B—C2B | 1.352 (3) | C11B—H11B | 0.9300 |
N1B—C6B | 1.362 (3) | C12B—C13B | 1.363 (4) |
N1B—H1B | 0.8600 | C13B—C14B | 1.379 (3) |
N2B—C2B | 1.314 (3) | C13B—H13B | 0.9300 |
N2B—H2B1 | 0.8600 | C14B—H14B | 0.9300 |
N2B—H2B2 | 0.8600 | C9A—C14A | 1.382 (3) |
N3B—C2B | 1.336 (2) | C9A—C10A | 1.384 (3) |
N3B—C4B | 1.342 (2) | C10A—C11A | 1.377 (3) |
N4B—C4B | 1.330 (2) | C10A—H10A | 0.9300 |
N4B—H4B1 | 0.8600 | C11A—C12A | 1.361 (4) |
N4B—H4B2 | 0.8600 | C11A—H11A | 0.9300 |
N1A—C2A | 1.352 (3) | C12A—C13A | 1.369 (4) |
N1A—C6A | 1.362 (2) | C13A—C14A | 1.378 (3) |
N1A—H1A | 0.8600 | C13A—H13A | 0.9300 |
N2A—C2A | 1.324 (2) | C14A—H14A | 0.9300 |
N2A—H2A1 | 0.8600 | C9C—C14C | 1.380 (3) |
N2A—H2A2 | 0.8600 | C9C—C10C | 1.401 (3) |
N3A—C2A | 1.333 (2) | C10C—C11C | 1.378 (4) |
N3A—C4A | 1.351 (2) | C10C—H10C | 0.9300 |
N4A—C4A | 1.321 (2) | C11C—C12C | 1.364 (4) |
N4A—H4A1 | 0.8600 | C11C—H11C | 0.9300 |
N4A—H4A2 | 0.8600 | C12C—C13C | 1.368 (4) |
N1C—C2C | 1.349 (3) | C13C—C14C | 1.389 (3) |
N1C—C6C | 1.364 (3) | C13C—H13C | 0.9300 |
N1C—H1C | 0.8600 | C14C—H14C | 0.9300 |
N2C—C2C | 1.327 (3) | C15A—C16A | 1.369 (3) |
N2C—H2C1 | 0.8600 | C15A—C24A | 1.425 (3) |
N2C—H2C2 | 0.8600 | C16A—C17A | 1.403 (3) |
N3C—C2C | 1.328 (3) | C16A—H16A | 0.9300 |
N3C—C4C | 1.339 (3) | C17A—C18A | 1.352 (3) |
N4C—C4C | 1.334 (3) | C17A—H17A | 0.9300 |
N4C—H4C1 | 0.8600 | C18A—C19A | 1.419 (3) |
N4C—H4C2 | 0.8600 | C18A—H18A | 0.9300 |
C4B—C5B | 1.433 (3) | C19A—C24A | 1.425 (3) |
C5B—C6B | 1.365 (3) | C19A—C20A | 1.432 (3) |
C5B—C9B | 1.490 (3) | C20A—C21A | 1.364 (3) |
C6B—C7B | 1.495 (3) | C21A—C22A | 1.408 (3) |
C7B—C8B | 1.517 (4) | C21A—H21A | 0.9300 |
C7B—H7B1 | 0.9700 | C22A—C23A | 1.352 (3) |
C7B—H7B2 | 0.9700 | C22A—H22A | 0.9300 |
C8B—H8B1 | 0.9600 | C23A—C24A | 1.424 (3) |
C8B—H8B2 | 0.9600 | C23A—H23A | 0.9300 |
C8B—H8B3 | 0.9600 | C16B—C15B | 1.361 (3) |
C4A—C5A | 1.431 (3) | C16B—C22Bi | 1.401 (3) |
C5A—C6A | 1.356 (3) | C16B—H16B | 0.9300 |
C5A—C9A | 1.486 (3) | C15B—C24B | 1.429 (3) |
C6A—C7A | 1.492 (3) | C24B—C23B | 1.415 (3) |
C7A—C8A | 1.507 (4) | C24B—C24Bi | 1.430 (4) |
C7A—H7A1 | 0.9700 | C23B—C22B | 1.358 (3) |
C7A—H7A2 | 0.9700 | C23B—H23B | 0.9300 |
C8A—H8A1 | 0.9600 | C22B—C16Bi | 1.401 (3) |
C8A—H8A2 | 0.9600 | C22B—H22B | 0.9300 |
C8A—H8A3 | 0.9600 | ||
O3A—S1A—O2A | 113.98 (11) | C8C—C7C—H7C1 | 109.1 |
O3A—S1A—O1A | 112.48 (11) | C6C—C7C—H7C2 | 109.1 |
O2A—S1A—O1A | 111.17 (9) | C8C—C7C—H7C2 | 109.1 |
O3A—S1A—C15A | 104.88 (10) | H7C1—C7C—H7C2 | 107.8 |
O2A—S1A—C15A | 108.05 (10) | C7C—C8C—H8C1 | 109.5 |
O1A—S1A—C15A | 105.63 (10) | C7C—C8C—H8C2 | 109.5 |
O6A—S2A—O4A | 113.05 (10) | H8C1—C8C—H8C2 | 109.5 |
O6A—S2A—O5A | 113.16 (12) | C7C—C8C—H8C3 | 109.5 |
O4A—S2A—O5A | 111.22 (11) | H8C1—C8C—H8C3 | 109.5 |
O6A—S2A—C20A | 105.59 (10) | H8C2—C8C—H8C3 | 109.5 |
O4A—S2A—C20A | 105.14 (10) | C14B—C9B—C10B | 117.8 (2) |
O5A—S2A—C20A | 108.07 (10) | C14B—C9B—C5B | 121.2 (2) |
O2B—S3B—O1B | 112.36 (10) | C10B—C9B—C5B | 120.9 (2) |
O2B—S3B—O3B | 112.17 (9) | C11B—C10B—C9B | 121.0 (2) |
O1B—S3B—O3B | 112.84 (11) | C11B—C10B—H10B | 119.5 |
O2B—S3B—C15B | 106.37 (11) | C9B—C10B—H10B | 119.5 |
O1B—S3B—C15B | 106.85 (9) | C12B—C11B—C10B | 119.1 (2) |
O3B—S3B—C15B | 105.64 (10) | C12B—C11B—H11B | 120.4 |
C2B—N1B—C6B | 122.19 (16) | C10B—C11B—H11B | 120.4 |
C2B—N1B—H1B | 118.9 | C13B—C12B—C11B | 121.6 (2) |
C6B—N1B—H1B | 118.9 | C13B—C12B—Cl1B | 119.1 (2) |
C2B—N2B—H2B1 | 120.0 | C11B—C12B—Cl1B | 119.4 (2) |
C2B—N2B—H2B2 | 120.0 | C12B—C13B—C14B | 118.8 (2) |
H2B1—N2B—H2B2 | 120.0 | C12B—C13B—H13B | 120.6 |
C2B—N3B—C4B | 118.29 (17) | C14B—C13B—H13B | 120.6 |
C4B—N4B—H4B1 | 120.0 | C13B—C14B—C9B | 121.6 (2) |
C4B—N4B—H4B2 | 120.0 | C13B—C14B—H14B | 119.2 |
H4B1—N4B—H4B2 | 120.0 | C9B—C14B—H14B | 119.2 |
C2A—N1A—C6A | 121.98 (16) | C14A—C9A—C10A | 118.8 (2) |
C2A—N1A—H1A | 119.0 | C14A—C9A—C5A | 120.8 (2) |
C6A—N1A—H1A | 119.0 | C10A—C9A—C5A | 120.38 (19) |
C2A—N2A—H2A1 | 120.0 | C11A—C10A—C9A | 120.7 (2) |
C2A—N2A—H2A2 | 120.0 | C11A—C10A—H10A | 119.7 |
H2A1—N2A—H2A2 | 120.0 | C9A—C10A—H10A | 119.7 |
C2A—N3A—C4A | 117.05 (17) | C12A—C11A—C10A | 119.2 (3) |
C4A—N4A—H4A1 | 120.0 | C12A—C11A—H11A | 120.4 |
C4A—N4A—H4A2 | 120.0 | C10A—C11A—H11A | 120.4 |
H4A1—N4A—H4A2 | 120.0 | C11A—C12A—C13A | 121.5 (2) |
C2C—N1C—C6C | 122.05 (19) | C11A—C12A—Cl1A | 119.3 (2) |
C2C—N1C—H1C | 119.0 | C13A—C12A—Cl1A | 119.2 (2) |
C6C—N1C—H1C | 119.0 | C12A—C13A—C14A | 119.2 (2) |
C2C—N2C—H2C1 | 120.0 | C12A—C13A—H13A | 120.4 |
C2C—N2C—H2C2 | 120.0 | C14A—C13A—H13A | 120.4 |
H2C1—N2C—H2C2 | 120.0 | C13A—C14A—C9A | 120.5 (2) |
C2C—N3C—C4C | 117.2 (2) | C13A—C14A—H14A | 119.7 |
C4C—N4C—H4C1 | 120.0 | C9A—C14A—H14A | 119.7 |
C4C—N4C—H4C2 | 120.0 | C14C—C9C—C10C | 117.9 (2) |
H4C1—N4C—H4C2 | 120.0 | C14C—C9C—C5C | 120.5 (2) |
N2B—C2B—N3B | 120.38 (18) | C10C—C9C—C5C | 121.6 (2) |
N2B—C2B—N1B | 118.53 (17) | C11C—C10C—C9C | 120.8 (3) |
N3B—C2B—N1B | 121.08 (18) | C11C—C10C—H10C | 119.6 |
N4B—C4B—N3B | 116.32 (18) | C9C—C10C—H10C | 119.6 |
N4B—C4B—C5B | 120.97 (18) | C12C—C11C—C10C | 119.7 (3) |
N3B—C4B—C5B | 122.70 (17) | C12C—C11C—H11C | 120.1 |
C6B—C5B—C4B | 116.46 (18) | C10C—C11C—H11C | 120.1 |
C6B—C5B—C9B | 122.39 (18) | C11C—C12C—C13C | 121.1 (3) |
C4B—C5B—C9B | 121.14 (17) | C11C—C12C—Cl1C | 119.9 (2) |
N1B—C6B—C5B | 119.25 (18) | C13C—C12C—Cl1C | 118.9 (3) |
N1B—C6B—C7B | 115.14 (17) | C12C—C13C—C14C | 119.3 (3) |
C5B—C6B—C7B | 125.60 (19) | C12C—C13C—H13C | 120.4 |
C6B—C7B—C8B | 112.5 (2) | C14C—C13C—H13C | 120.4 |
C6B—C7B—H7B1 | 109.1 | C9C—C14C—C13C | 121.1 (3) |
C8B—C7B—H7B1 | 109.1 | C9C—C14C—H14C | 119.4 |
C6B—C7B—H7B2 | 109.1 | C13C—C14C—H14C | 119.4 |
C8B—C7B—H7B2 | 109.1 | C16A—C15A—C24A | 120.9 (2) |
H7B1—C7B—H7B2 | 107.8 | C16A—C15A—S1A | 117.87 (16) |
C7B—C8B—H8B1 | 109.5 | C24A—C15A—S1A | 121.11 (16) |
C7B—C8B—H8B2 | 109.5 | C15A—C16A—C17A | 119.8 (2) |
H8B1—C8B—H8B2 | 109.5 | C15A—C16A—H16A | 120.1 |
C7B—C8B—H8B3 | 109.5 | C17A—C16A—H16A | 120.1 |
H8B1—C8B—H8B3 | 109.5 | C18A—C17A—C16A | 121.1 (2) |
H8B2—C8B—H8B3 | 109.5 | C18A—C17A—H17A | 119.4 |
N2A—C2A—N3A | 120.50 (18) | C16A—C17A—H17A | 119.4 |
N2A—C2A—N1A | 117.41 (17) | C17A—C18A—C19A | 120.9 (2) |
N3A—C2A—N1A | 122.09 (18) | C17A—C18A—H18A | 119.5 |
N4A—C4A—N3A | 117.50 (18) | C19A—C18A—H18A | 119.5 |
N4A—C4A—C5A | 119.60 (18) | C18A—C19A—C24A | 118.70 (18) |
N3A—C4A—C5A | 122.90 (17) | C18A—C19A—C20A | 122.5 (2) |
C6A—C5A—C4A | 117.04 (18) | C24A—C19A—C20A | 118.79 (18) |
C6A—C5A—C9A | 122.25 (18) | C21A—C20A—C19A | 120.0 (2) |
C4A—C5A—C9A | 120.71 (16) | C21A—C20A—S2A | 118.20 (16) |
C5A—C6A—N1A | 118.92 (18) | C19A—C20A—S2A | 121.68 (16) |
C5A—C6A—C7A | 124.91 (19) | C20A—C21A—C22A | 120.9 (2) |
N1A—C6A—C7A | 116.01 (17) | C20A—C21A—H21A | 119.6 |
C6A—C7A—C8A | 111.1 (2) | C22A—C21A—H21A | 119.6 |
C6A—C7A—H7A1 | 109.4 | C23A—C22A—C21A | 120.7 (2) |
C8A—C7A—H7A1 | 109.4 | C23A—C22A—H22A | 119.6 |
C6A—C7A—H7A2 | 109.4 | C21A—C22A—H22A | 119.6 |
C8A—C7A—H7A2 | 109.4 | C22A—C23A—C24A | 120.9 (2) |
H7A1—C7A—H7A2 | 108.0 | C22A—C23A—H23A | 119.6 |
C7A—C8A—H8A1 | 109.5 | C24A—C23A—H23A | 119.6 |
C7A—C8A—H8A2 | 109.5 | C23A—C24A—C19A | 118.70 (18) |
H8A1—C8A—H8A2 | 109.5 | C23A—C24A—C15A | 122.9 (2) |
C7A—C8A—H8A3 | 109.5 | C19A—C24A—C15A | 118.37 (18) |
H8A1—C8A—H8A3 | 109.5 | C15B—C16B—C22Bi | 120.0 (2) |
H8A2—C8A—H8A3 | 109.5 | C15B—C16B—H16B | 120.0 |
N2C—C2C—N3C | 119.7 (2) | C22Bi—C16B—H16B | 120.0 |
N2C—C2C—N1C | 118.2 (2) | C16B—C15B—C24B | 121.2 (2) |
N3C—C2C—N1C | 122.2 (2) | C16B—C15B—S3B | 118.05 (17) |
N4C—C4C—N3C | 115.9 (2) | C24B—C15B—S3B | 120.72 (17) |
N4C—C4C—C5C | 121.0 (2) | C23B—C24B—C15B | 123.1 (2) |
N3C—C4C—C5C | 123.2 (2) | C23B—C24B—C24Bi | 118.9 (2) |
C6C—C5C—C4C | 116.6 (2) | C15B—C24B—C24Bi | 117.9 (2) |
C6C—C5C—C9C | 122.4 (2) | C22B—C23B—C24B | 120.8 (2) |
C4C—C5C—C9C | 121.0 (2) | C22B—C23B—H23B | 119.6 |
C5C—C6C—N1C | 118.6 (2) | C24B—C23B—H23B | 119.6 |
C5C—C6C—C7C | 126.2 (2) | C23B—C22B—C16Bi | 121.1 (2) |
N1C—C6C—C7C | 115.2 (2) | C23B—C22B—H22B | 119.4 |
C6C—C7C—C8C | 112.5 (2) | C16Bi—C22B—H22B | 119.4 |
C6C—C7C—H7C1 | 109.1 | ||
C4B—N3B—C2B—N2B | −179.3 (2) | C9A—C10A—C11A—C12A | −1.2 (4) |
C4B—N3B—C2B—N1B | −0.1 (3) | C10A—C11A—C12A—C13A | −0.2 (4) |
C6B—N1B—C2B—N2B | −179.7 (2) | C10A—C11A—C12A—Cl1A | −179.3 (2) |
C6B—N1B—C2B—N3B | 1.1 (3) | C11A—C12A—C13A—C14A | 1.4 (4) |
C2B—N3B—C4B—N4B | 178.9 (2) | Cl1A—C12A—C13A—C14A | −179.6 (2) |
C2B—N3B—C4B—C5B | −0.7 (3) | C12A—C13A—C14A—C9A | −1.1 (4) |
N4B—C4B—C5B—C6B | −179.1 (2) | C10A—C9A—C14A—C13A | −0.3 (3) |
N3B—C4B—C5B—C6B | 0.6 (3) | C5A—C9A—C14A—C13A | 179.8 (2) |
N4B—C4B—C5B—C9B | −0.3 (3) | C6C—C5C—C9C—C14C | −112.0 (3) |
N3B—C4B—C5B—C9B | 179.3 (2) | C4C—C5C—C9C—C14C | 68.8 (3) |
C2B—N1B—C6B—C5B | −1.2 (3) | C6C—C5C—C9C—C10C | 67.5 (3) |
C2B—N1B—C6B—C7B | 179.8 (2) | C4C—C5C—C9C—C10C | −111.7 (3) |
C4B—C5B—C6B—N1B | 0.4 (3) | C14C—C9C—C10C—C11C | 0.4 (4) |
C9B—C5B—C6B—N1B | −178.3 (2) | C5C—C9C—C10C—C11C | −179.2 (3) |
C4B—C5B—C6B—C7B | 179.3 (2) | C9C—C10C—C11C—C12C | −0.5 (5) |
C9B—C5B—C6B—C7B | 0.5 (4) | C10C—C11C—C12C—C13C | 0.3 (5) |
N1B—C6B—C7B—C8B | 76.2 (3) | C10C—C11C—C12C—Cl1C | −179.9 (2) |
C5B—C6B—C7B—C8B | −102.7 (3) | C11C—C12C—C13C—C14C | 0.0 (4) |
C4A—N3A—C2A—N2A | 178.3 (2) | Cl1C—C12C—C13C—C14C | −179.8 (2) |
C4A—N3A—C2A—N1A | −0.9 (3) | C10C—C9C—C14C—C13C | −0.1 (4) |
C6A—N1A—C2A—N2A | −177.9 (2) | C5C—C9C—C14C—C13C | 179.5 (2) |
C6A—N1A—C2A—N3A | 1.4 (3) | C12C—C13C—C14C—C9C | −0.1 (4) |
C2A—N3A—C4A—N4A | 179.8 (2) | O3A—S1A—C15A—C16A | −112.70 (18) |
C2A—N3A—C4A—C5A | −0.3 (3) | O2A—S1A—C15A—C16A | 125.37 (18) |
N4A—C4A—C5A—C6A | −179.1 (2) | O1A—S1A—C15A—C16A | 6.3 (2) |
N3A—C4A—C5A—C6A | 1.1 (3) | O3A—S1A—C15A—C24A | 63.79 (18) |
N4A—C4A—C5A—C9A | 0.6 (3) | O2A—S1A—C15A—C24A | −58.14 (18) |
N3A—C4A—C5A—C9A | −179.2 (2) | O1A—S1A—C15A—C24A | −177.19 (15) |
C4A—C5A—C6A—N1A | −0.6 (3) | C24A—C15A—C16A—C17A | −1.3 (3) |
C9A—C5A—C6A—N1A | 179.72 (19) | S1A—C15A—C16A—C17A | 175.16 (18) |
C4A—C5A—C6A—C7A | −175.9 (2) | C15A—C16A—C17A—C18A | −1.5 (4) |
C9A—C5A—C6A—C7A | 4.4 (4) | C16A—C17A—C18A—C19A | 2.9 (4) |
C2A—N1A—C6A—C5A | −0.6 (3) | C17A—C18A—C19A—C24A | −1.4 (3) |
C2A—N1A—C6A—C7A | 175.2 (2) | C17A—C18A—C19A—C20A | 178.1 (2) |
C5A—C6A—C7A—C8A | 92.5 (3) | C18A—C19A—C20A—C21A | −178.5 (2) |
N1A—C6A—C7A—C8A | −82.9 (3) | C24A—C19A—C20A—C21A | 1.0 (3) |
C4C—N3C—C2C—N2C | 176.48 (19) | C18A—C19A—C20A—S2A | 5.4 (3) |
C4C—N3C—C2C—N1C | −4.2 (3) | C24A—C19A—C20A—S2A | −175.14 (14) |
C6C—N1C—C2C—N2C | −178.75 (18) | O6A—S2A—C20A—C21A | −111.94 (18) |
C6C—N1C—C2C—N3C | 1.9 (3) | O4A—S2A—C20A—C21A | 7.8 (2) |
C2C—N3C—C4C—N4C | −176.2 (2) | O5A—S2A—C20A—C21A | 126.69 (18) |
C2C—N3C—C4C—C5C | 3.1 (3) | O6A—S2A—C20A—C19A | 64.27 (19) |
N4C—C4C—C5C—C6C | 179.5 (2) | O4A—S2A—C20A—C19A | −175.96 (16) |
N3C—C4C—C5C—C6C | 0.3 (3) | O5A—S2A—C20A—C19A | −57.10 (19) |
N4C—C4C—C5C—C9C | −1.2 (3) | C19A—C20A—C21A—C22A | −1.1 (3) |
N3C—C4C—C5C—C9C | 179.6 (2) | S2A—C20A—C21A—C22A | 175.14 (17) |
C4C—C5C—C6C—N1C | −2.7 (3) | C20A—C21A—C22A—C23A | 0.5 (3) |
C9C—C5C—C6C—N1C | 178.06 (19) | C21A—C22A—C23A—C24A | 0.2 (3) |
C4C—C5C—C6C—C7C | 179.7 (2) | C22A—C23A—C24A—C19A | −0.3 (3) |
C9C—C5C—C6C—C7C | 0.5 (3) | C22A—C23A—C24A—C15A | −179.78 (19) |
C2C—N1C—C6C—C5C | 1.7 (3) | C18A—C19A—C24A—C23A | 179.25 (18) |
C2C—N1C—C6C—C7C | 179.58 (19) | C20A—C19A—C24A—C23A | −0.3 (3) |
C5C—C6C—C7C—C8C | 82.4 (3) | C18A—C19A—C24A—C15A | −1.3 (3) |
N1C—C6C—C7C—C8C | −95.2 (3) | C20A—C19A—C24A—C15A | 179.20 (17) |
C6B—C5B—C9B—C14B | 68.6 (3) | C16A—C15A—C24A—C23A | −177.9 (2) |
C4B—C5B—C9B—C14B | −110.1 (3) | S1A—C15A—C24A—C23A | 5.7 (3) |
C6B—C5B—C9B—C10B | −111.3 (2) | C16A—C15A—C24A—C19A | 2.7 (3) |
C4B—C5B—C9B—C10B | 70.0 (3) | S1A—C15A—C24A—C19A | −173.71 (14) |
C14B—C9B—C10B—C11B | −0.9 (3) | C22Bi—C16B—C15B—C24B | −0.7 (4) |
C5B—C9B—C10B—C11B | 179.0 (2) | C22Bi—C16B—C15B—S3B | −179.7 (2) |
C9B—C10B—C11B—C12B | −0.3 (4) | O2B—S3B—C15B—C16B | 114.6 (2) |
C10B—C11B—C12B—C13B | 1.0 (4) | O1B—S3B—C15B—C16B | −125.21 (19) |
C10B—C11B—C12B—Cl1B | −178.60 (18) | O3B—S3B—C15B—C16B | −4.8 (2) |
C11B—C12B—C13B—C14B | −0.3 (4) | O2B—S3B—C15B—C24B | −64.4 (2) |
Cl1B—C12B—C13B—C14B | 179.3 (2) | O1B—S3B—C15B—C24B | 55.8 (2) |
C12B—C13B—C14B—C9B | −1.0 (4) | O3B—S3B—C15B—C24B | 176.22 (17) |
C10B—C9B—C14B—C13B | 1.6 (4) | C16B—C15B—C24B—C23B | −179.8 (2) |
C5B—C9B—C14B—C13B | −178.3 (2) | S3B—C15B—C24B—C23B | −0.9 (3) |
C6A—C5A—C9A—C14A | −105.4 (3) | C16B—C15B—C24B—C24Bi | 1.4 (4) |
C4A—C5A—C9A—C14A | 75.0 (3) | S3B—C15B—C24B—C24Bi | −179.7 (2) |
C6A—C5A—C9A—C10A | 74.8 (3) | C15B—C24B—C23B—C22B | −179.1 (2) |
C4A—C5A—C9A—C10A | −104.9 (2) | C24Bi—C24B—C23B—C22B | −0.3 (4) |
C14A—C9A—C10A—C11A | 1.5 (3) | C24B—C23B—C22B—C16Bi | −0.4 (4) |
C5A—C9A—C10A—C11A | −178.7 (2) |
Symmetry code: (i) −x, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2B1···O1Bii | 0.86 | 2.21 | 3.030 (3) | 158 |
N1A—H1A···O1A | 0.86 | 1.90 | 2.752 (3) | 170 |
N1B—H1B···O3Biii | 0.86 | 1.95 | 2.778 (3) | 160 |
N1C—H1C···O4Aiv | 0.86 | 1.90 | 2.755 (3) | 173 |
N2B—H2B2···O2Biii | 0.86 | 2.04 | 2.889 (3) | 169 |
N4B—H4B1···N3Aii | 0.86 | 2.35 | 3.192 (3) | 165 |
N4B—H4B2···O5Av | 0.86 | 2.27 | 2.940 (2) | 135 |
N2A—H2A1···O6Avi | 0.86 | 2.38 | 2.965 (3) | 125 |
N2A—H2A2···O2A | 0.86 | 2.10 | 2.936 (3) | 164 |
N4A—H4A1···N3Bvii | 0.86 | 2.11 | 2.955 (3) | 170 |
N4A—H4A2···O1B | 0.86 | 2.17 | 2.913 (2) | 145 |
N2C—H2C1···O3Aviii | 0.86 | 1.97 | 2.818 (3) | 169 |
N2C—H2C2···O5Aiv | 0.86 | 2.27 | 3.102 (3) | 162 |
N4C—H4C2···O2A | 0.86 | 2.32 | 3.027 (3) | 140 |
C8B—H8B1···O3Biii | 0.96 | 2.59 | 3.380 (4) | 140 |
Symmetry codes: (ii) x+1, y, z; (iii) −x+1, −y, −z+2; (iv) −x, −y+2, −z+1; (v) x+1, y−1, z; (vi) x, y−1, z; (vii) x−1, y, z; (viii) −x+1, −y+1, −z+1. |
Compound | Angle |
Neutral TMPa | 115.5 (5) |
(I) | 119.5 (2) |
(II) | 120.3 (2) |
(III) | 120.23 (19) |
((IV) | 119.92 (14) |
(V), Molecule A | 120.09 (19) |
(V), Molecule B | 120.31 (19) |
Neutral PMNb, Molecule A | 116.25 (18) |
Neutral PMNb, Molecule A | 116.09 (18) |
(VI) | 121.2 (2) |
((VII)) | 120.8 (3) |
(VIII) | 121.5 (2) |
(IX), Molecule A | 121.97 (19) |
(IX), Molecule B | 122.21 (19) |
(IX), Molecule C | 122.0 (2) |
Reference: (a) Koetzle & Williams (1976); (b) Sethuraman & Muthiah (2002). |
Compound | Torsion angle | Dihedral angle pyrimidine/phenyl ring | |
τ1(C4—C5—C7—C8) | τ2(C5—C7—C8—C9) | ||
Neutral TMPa | -89.4 (1) | 153.3 (1) | 71.33 (2) |
(I) | -75.0 (3) | -22.3 (3) | 86.00 (10) |
(II) | -56.5 (4) | -37.0 (4) | 77.01 (12) |
(III)) | -56.6 (3) | -37.0 (3) | 77.26 (10) |
(IV)) | 74.8 (2) | 23.7 (2) | 88.16 (7) |
(V), Molecule A | -177.2 (2) | -175. 37 (19) | 83.77 (11) |
(V), Molecule B | 83.5 (3) | 86.5 (3) | 89.10 (11) |
Reference: (a) Koetzle & Williams (1976). |
Compound | Torsion angle C5—C6—C7—C8 | Dihedral angle pyrimidine/phenyl |
Neutral PMNa, Molecule A | 89.5 (2) | 74.4 (1) |
Neutral PMNa, Molecule B | 97.8 (1) | 82.4 (1) |
(VI) | 97.2 (4) | 80.42 (13) |
(VII) | -105.7 (4) | 73.24 (15) |
(VIII) | 110.0 (4) | 69.56 (17) |
(IX), Molecule A | 92.6 (3) | 74.50 (13) |
(IX), Molecule B | -102.7 (3) | 68.86 (12) |
(IX), Molecule C | 82.4 (3) | 68.69 (13) |
Reference: (a) Sethuraman & Muthiah (2002). |