organic compounds
5-(7-Methanesulfonyl-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine mesylate
aResearch Division, Chugai Pharmaceutical Co. Ltd., 1-135 Komakado, Gotemba, Shizuoka 412-8513, Japan, and bPharmaceutical Technology Division, Chugai Pharmaceutical Co. Ltd., 5-5-1 Ukima, Kita-ku, Tokyo 115-8543, Japan
*Correspondence e-mail: aoki.masahide18@chugai-pharm.co.jp
In the title compound, C15H20N7O3S+·CH3O3S− (CH5132799 mesylate), two molecular entities form a salt with proton transfer from methanesulfonic acid to the aminopyrimidine moiety of CH5132799. In the crystal, methanesulfonate is retained by bifurcated O⋯H—N hydrogen bonds and an N+—H⋯O− charge-assisted hydrogen bond.
Keywords: crystal structure; mesylate; active pharmaceutical ingredient.
CCDC reference: 1573598
Structure description
5-(7-Methanesulfonyl-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine (CH5132799) was synthesized as an antitumor PI3K inhibitor (Ohwada et al., 2011; Tanaka et al., 2011) and crystallized with methanesulfonic acid to improve its aqueous solubility. Single crystal X-ray structure analysis revealed that the three S—O bond lengths of methanesulfonate to be 1.444 (2), 1.473 (2), and 1.475 (2) Å, and it was confirmed that CH5132799 and methanesulfonic acid form a molecular salt with proton transfer from methanesulfonic acid to the aminopyrimidine moiety of CH5132799. In the crystal, methanesulfonate is retained by bifurcated O30⋯H19B(H19A#)—N19(N19#) hydrogen bonds and an N+17—H17⋯O−28 charge-assisted hydrogen bond (Figs. 1 and 2, and Table 1).
Synthesis and crystallization
CH5132799 was synthesized according to the patented process (Shimma et al., 2008; Ebiike et al., 2009). CH5132799 (1.0 eq.) was added to a stirred solution of methanesulfonic acid (2.3 weq.) and water (2.5 weq.). L-Cysteine (0.058 weq.) was then added to the solution and the mixture was continuously stirred for an additional 3 h. The resulting solution was filtered, and the equipment was rinsed with a solution of methanesulfonic acid (0.22 weq.) and water (2.1 weq.). The filtrate and the rinse were combined, and acetone (6.2 veq.) was added slowly to this stirred solution at room temperature. Stirring was continued for at least 2 h and the presence of the solids was confirmed. Further acetone (19 veq.) was added to the mixture, which was stirred for an additional hour at the same temperature. This mixture was then filtered, and the solids were washed twice with acetone (each 4.0 veq). The solids were collected and dried under reduced pressure to afford CH5132799 mesylate as yellow crystals (typical yield 90%).
Refinement
Crystal data, data collection, and .
details are summarized in Table 2Structural data
CCDC reference: 1573598
https://doi.org/10.1107/S2414314617012925/bx4008sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012925/bx4008Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617012925/bx4008Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S2414314617012925/bx4008Isup4.cml
Data collection: RAPID-AUTO (Rigaku, 1999); cell
RAPID-AUTO (Rigaku, 1999); data reduction: RAPID-AUTO (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2016), publCIF (Westrip, 2010).C15H20N7O3S+·CH3O3S− | Z = 2 |
Mr = 473.52 | F(000) = 496.00 |
Triclinic, P1 | Dx = 1.560 Mg m−3 |
a = 9.45151 (17) Å | Cu Kα radiation, λ = 1.54187 Å |
b = 10.7942 (2) Å | Cell parameters from 9509 reflections |
c = 11.3964 (2) Å | θ = 4.5–68.2° |
α = 63.3450 (7)° | µ = 2.86 mm−1 |
β = 76.7692 (8)° | T = 93 K |
γ = 88.1338 (8)° | Block, yellow |
V = 1008.24 (3) Å3 | 0.29 × 0.08 × 0.04 mm |
Rigaku R-AXIS RAPID-II diffractometer | 3621 independent reflections |
Radiation source: fine-focus rotating anode x-ray, RIGAKU | 2942 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.061 |
ω–scan | θmax = 68.2°, θmin = 4.5° |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | h = −10→10 |
Tmin = 0.588, Tmax = 0.884 | k = −12→12 |
17410 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3 |
3621 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8116 (3) | 0.3631 (2) | 0.1438 (2) | 0.0190 (5) | |
H1A | 0.9127 | 0.3646 | 0.0938 | 0.023* | |
H1B | 0.8142 | 0.3500 | 0.2350 | 0.023* | |
C2 | 0.7479 (3) | 0.4990 (2) | 0.0693 (2) | 0.0179 (5) | |
H2A | 0.6521 | 0.5012 | 0.1257 | 0.021* | |
H2B | 0.8130 | 0.5771 | 0.0549 | 0.021* | |
O3 | 0.72976 (18) | 0.51726 (16) | −0.05928 (15) | 0.0208 (4) | |
C4 | 0.6381 (3) | 0.4043 (2) | −0.0418 (2) | 0.0197 (5) | |
H4A | 0.6267 | 0.4188 | −0.1313 | 0.024* | |
H4B | 0.5403 | 0.4028 | 0.0137 | 0.024* | |
C5 | 0.6999 (3) | 0.2665 (2) | 0.0255 (2) | 0.0169 (5) | |
H5A | 0.6319 | 0.1901 | 0.0405 | 0.020* | |
H5B | 0.7941 | 0.2638 | −0.0328 | 0.020* | |
N6 | 0.7213 (2) | 0.24915 (19) | 0.15512 (18) | 0.0173 (4) | |
C7 | 0.6958 (2) | 0.1218 (2) | 0.2668 (2) | 0.0148 (5) | |
N8 | 0.6153 (2) | 0.02500 (19) | 0.25782 (18) | 0.0167 (4) | |
C9 | 0.5905 (3) | −0.0948 (2) | 0.3679 (2) | 0.0154 (5) | |
C10 | 0.6395 (2) | −0.1294 (2) | 0.4856 (2) | 0.0148 (5) | |
C11 | 0.7197 (2) | −0.0231 (2) | 0.4821 (2) | 0.0144 (5) | |
N12 | 0.7487 (2) | 0.10429 (18) | 0.37118 (18) | 0.0151 (4) | |
C13 | 0.7882 (2) | −0.0333 (2) | 0.5906 (2) | 0.0141 (5) | |
C14 | 0.7765 (3) | −0.1507 (2) | 0.7171 (2) | 0.0184 (5) | |
H14 | 0.7199 | −0.2312 | 0.7352 | 0.022* | |
N15 | 0.8385 (2) | −0.15666 (19) | 0.81191 (19) | 0.0194 (5) | |
C16 | 0.9182 (2) | −0.0421 (2) | 0.7856 (2) | 0.0157 (5) | |
N17 | 0.9382 (2) | 0.07316 (19) | 0.66444 (17) | 0.0147 (4) | |
H17 | 0.9948 | 0.1450 | 0.6481 | 0.018* | |
C18 | 0.8733 (2) | 0.0790 (2) | 0.5699 (2) | 0.0151 (5) | |
H18 | 0.8859 | 0.1619 | 0.4871 | 0.018* | |
N19 | 0.9806 (2) | −0.0410 (2) | 0.87759 (19) | 0.0213 (5) | |
H19A | 0.9700 | −0.1152 | 0.9562 | 0.026* | |
H19B | 1.0327 | 0.0339 | 0.8603 | 0.026* | |
C20 | 0.5912 (3) | −0.2799 (2) | 0.5840 (2) | 0.0172 (5) | |
H20A | 0.5197 | −0.2874 | 0.6658 | 0.021* | |
H20B | 0.6755 | −0.3324 | 0.6115 | 0.021* | |
C21 | 0.5209 (3) | −0.3350 (2) | 0.5051 (2) | 0.0188 (5) | |
H21A | 0.5823 | −0.4013 | 0.4830 | 0.023* | |
H21B | 0.4228 | −0.3820 | 0.5581 | 0.023* | |
N22 | 0.5113 (2) | −0.20763 (19) | 0.37949 (18) | 0.0190 (5) | |
S23 | 0.45298 (6) | −0.21101 (6) | 0.25455 (6) | 0.01767 (17) | |
O24 | 0.36279 (17) | −0.09916 (17) | 0.20638 (16) | 0.0233 (4) | |
O25 | 0.39192 (19) | −0.35083 (17) | 0.30865 (16) | 0.0270 (4) | |
C26 | 0.6083 (3) | −0.1798 (2) | 0.1241 (2) | 0.0204 (5) | |
H26A | 0.5800 | −0.1838 | 0.0483 | 0.024* | |
H26B | 0.6764 | −0.2505 | 0.1572 | 0.024* | |
H26C | 0.6554 | −0.0874 | 0.0938 | 0.024* | |
S27 | 0.91174 (6) | 0.64832 (6) | 0.29026 (5) | 0.01677 (17) | |
O28 | 0.89847 (17) | 0.70007 (16) | 0.39179 (15) | 0.0195 (4) | |
O29 | 0.78257 (18) | 0.56674 (16) | 0.30994 (16) | 0.0232 (4) | |
O30 | 0.95755 (18) | 0.76462 (16) | 0.15328 (15) | 0.0203 (4) | |
C31 | 1.0534 (3) | 0.5373 (3) | 0.3124 (2) | 0.0234 (6) | |
H31A | 1.1433 | 0.5887 | 0.3007 | 0.028* | |
H31B | 1.0682 | 0.5019 | 0.2453 | 0.028* | |
H31C | 1.0279 | 0.4592 | 0.4035 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0256 (14) | 0.0140 (12) | 0.0164 (12) | −0.0030 (10) | −0.0070 (11) | −0.0048 (10) |
C2 | 0.0268 (14) | 0.0143 (12) | 0.0130 (12) | −0.0005 (10) | −0.0081 (10) | −0.0050 (10) |
O3 | 0.0354 (10) | 0.0132 (8) | 0.0119 (8) | −0.0009 (7) | −0.0081 (7) | −0.0027 (7) |
C4 | 0.0292 (15) | 0.0151 (12) | 0.0164 (12) | 0.0017 (10) | −0.0085 (11) | −0.0069 (10) |
C5 | 0.0250 (14) | 0.0136 (12) | 0.0125 (11) | 0.0006 (10) | −0.0073 (10) | −0.0049 (10) |
N6 | 0.0283 (12) | 0.0109 (10) | 0.0116 (10) | −0.0025 (8) | −0.0087 (9) | −0.0022 (8) |
C7 | 0.0187 (13) | 0.0123 (11) | 0.0146 (11) | 0.0029 (9) | −0.0041 (10) | −0.0072 (10) |
N8 | 0.0234 (11) | 0.0133 (10) | 0.0134 (10) | −0.0009 (8) | −0.0066 (8) | −0.0049 (8) |
C9 | 0.0197 (13) | 0.0134 (12) | 0.0148 (12) | 0.0018 (9) | −0.0037 (10) | −0.0081 (10) |
C10 | 0.0207 (13) | 0.0123 (11) | 0.0110 (11) | 0.0007 (9) | −0.0021 (9) | −0.0059 (10) |
C11 | 0.0188 (13) | 0.0115 (11) | 0.0111 (11) | 0.0014 (9) | −0.0017 (9) | −0.0043 (9) |
N12 | 0.0213 (11) | 0.0112 (10) | 0.0120 (10) | 0.0008 (8) | −0.0059 (8) | −0.0036 (8) |
C13 | 0.0192 (13) | 0.0112 (11) | 0.0108 (11) | 0.0021 (9) | −0.0037 (9) | −0.0039 (9) |
C14 | 0.0271 (14) | 0.0133 (12) | 0.0162 (12) | 0.0007 (10) | −0.0073 (10) | −0.0067 (10) |
N15 | 0.0276 (12) | 0.0151 (10) | 0.0154 (10) | −0.0015 (9) | −0.0072 (9) | −0.0056 (9) |
C16 | 0.0199 (13) | 0.0155 (12) | 0.0130 (12) | 0.0047 (10) | −0.0054 (10) | −0.0071 (10) |
N17 | 0.0186 (11) | 0.0124 (10) | 0.0116 (9) | −0.0012 (8) | −0.0039 (8) | −0.0038 (8) |
C18 | 0.0199 (13) | 0.0122 (11) | 0.0106 (11) | 0.0032 (9) | −0.0037 (10) | −0.0031 (9) |
N19 | 0.0310 (12) | 0.0176 (11) | 0.0139 (10) | −0.0041 (9) | −0.0096 (9) | −0.0036 (9) |
C20 | 0.0236 (13) | 0.0142 (12) | 0.0131 (12) | −0.0006 (10) | −0.0041 (10) | −0.0057 (10) |
C21 | 0.0289 (14) | 0.0113 (11) | 0.0132 (11) | −0.0047 (10) | −0.0059 (10) | −0.0023 (10) |
N22 | 0.0323 (12) | 0.0111 (10) | 0.0130 (10) | −0.0045 (9) | −0.0077 (9) | −0.0036 (8) |
S23 | 0.0216 (3) | 0.0183 (3) | 0.0151 (3) | −0.0021 (2) | −0.0055 (2) | −0.0086 (3) |
O24 | 0.0204 (10) | 0.0291 (10) | 0.0245 (9) | 0.0087 (8) | −0.0091 (8) | −0.0144 (8) |
O25 | 0.0385 (11) | 0.0221 (10) | 0.0209 (9) | −0.0109 (8) | −0.0086 (8) | −0.0086 (8) |
C26 | 0.0221 (14) | 0.0231 (13) | 0.0184 (12) | 0.0030 (10) | −0.0054 (10) | −0.0114 (11) |
S27 | 0.0218 (3) | 0.0146 (3) | 0.0124 (3) | −0.0011 (2) | −0.0053 (2) | −0.0041 (2) |
O28 | 0.0260 (10) | 0.0174 (9) | 0.0153 (8) | −0.0024 (7) | −0.0040 (7) | −0.0079 (7) |
O29 | 0.0257 (10) | 0.0213 (9) | 0.0227 (9) | −0.0069 (8) | −0.0057 (8) | −0.0094 (8) |
O30 | 0.0278 (10) | 0.0161 (8) | 0.0107 (8) | 0.0006 (7) | −0.0054 (7) | −0.0004 (7) |
C31 | 0.0291 (15) | 0.0218 (13) | 0.0177 (13) | 0.0072 (11) | −0.0090 (11) | −0.0063 (11) |
C1—N6 | 1.461 (3) | N15—C16 | 1.345 (3) |
C1—C2 | 1.514 (3) | C16—N19 | 1.320 (3) |
C1—H1A | 0.9900 | C16—N17 | 1.358 (3) |
C1—H1B | 0.9900 | N17—C18 | 1.335 (3) |
C2—O3 | 1.438 (3) | N17—H17 | 0.8800 |
C2—H2A | 0.9900 | C18—H18 | 0.9500 |
C2—H2B | 0.9900 | N19—H19A | 0.8800 |
O3—C4 | 1.432 (3) | N19—H19B | 0.8800 |
C4—C5 | 1.506 (3) | C20—C21 | 1.544 (3) |
C4—H4A | 0.9900 | C20—H20A | 0.9900 |
C4—H4B | 0.9900 | C20—H20B | 0.9900 |
C5—N6 | 1.464 (3) | C21—N22 | 1.495 (3) |
C5—H5A | 0.9900 | C21—H21A | 0.9900 |
C5—H5B | 0.9900 | C21—H21B | 0.9900 |
N6—C7 | 1.371 (3) | N22—S23 | 1.6553 (19) |
C7—N12 | 1.329 (3) | S23—O24 | 1.4276 (17) |
C7—N8 | 1.365 (3) | S23—O25 | 1.4318 (16) |
N8—C9 | 1.315 (3) | S23—C26 | 1.750 (2) |
C9—N22 | 1.390 (3) | C26—H26A | 0.9800 |
C9—C10 | 1.407 (3) | C26—H26B | 0.9800 |
C10—C11 | 1.377 (3) | C26—H26C | 0.9800 |
C10—C20 | 1.511 (3) | S27—O29 | 1.4435 (16) |
C11—N12 | 1.368 (3) | S27—O30 | 1.4725 (15) |
C11—C13 | 1.483 (3) | S27—O28 | 1.4750 (15) |
C13—C18 | 1.375 (3) | S27—C31 | 1.752 (2) |
C13—C14 | 1.411 (3) | C31—H31A | 0.9800 |
C14—N15 | 1.319 (3) | C31—H31B | 0.9800 |
C14—H14 | 0.9500 | C31—H31C | 0.9800 |
N6—C1—C2 | 108.83 (19) | N19—C16—N17 | 118.7 (2) |
N6—C1—H1A | 109.9 | N15—C16—N17 | 121.3 (2) |
C2—C1—H1A | 109.9 | C18—N17—C16 | 120.96 (19) |
N6—C1—H1B | 109.9 | C18—N17—H17 | 119.5 |
C2—C1—H1B | 109.9 | C16—N17—H17 | 119.5 |
H1A—C1—H1B | 108.3 | N17—C18—C13 | 120.9 (2) |
O3—C2—C1 | 112.14 (18) | N17—C18—H18 | 119.6 |
O3—C2—H2A | 109.2 | C13—C18—H18 | 119.6 |
C1—C2—H2A | 109.2 | C16—N19—H19A | 120.0 |
O3—C2—H2B | 109.2 | C16—N19—H19B | 120.0 |
C1—C2—H2B | 109.2 | H19A—N19—H19B | 120.0 |
H2A—C2—H2B | 107.9 | C10—C20—C21 | 104.50 (18) |
C4—O3—C2 | 110.46 (16) | C10—C20—H20A | 110.9 |
O3—C4—C5 | 111.80 (19) | C21—C20—H20A | 110.9 |
O3—C4—H4A | 109.3 | C10—C20—H20B | 110.9 |
C5—C4—H4A | 109.3 | C21—C20—H20B | 110.9 |
O3—C4—H4B | 109.3 | H20A—C20—H20B | 108.9 |
C5—C4—H4B | 109.3 | N22—C21—C20 | 104.18 (17) |
H4A—C4—H4B | 107.9 | N22—C21—H21A | 110.9 |
N6—C5—C4 | 108.52 (18) | C20—C21—H21A | 110.9 |
N6—C5—H5A | 110.0 | N22—C21—H21B | 110.9 |
C4—C5—H5A | 110.0 | C20—C21—H21B | 110.9 |
N6—C5—H5B | 110.0 | H21A—C21—H21B | 108.9 |
C4—C5—H5B | 110.0 | C9—N22—C21 | 110.30 (18) |
H5A—C5—H5B | 108.4 | C9—N22—S23 | 124.24 (16) |
C7—N6—C1 | 122.34 (18) | C21—N22—S23 | 123.60 (14) |
C7—N6—C5 | 121.21 (18) | O24—S23—O25 | 119.02 (10) |
C1—N6—C5 | 113.79 (17) | O24—S23—N22 | 109.06 (10) |
N12—C7—N8 | 126.7 (2) | O25—S23—N22 | 104.35 (9) |
N12—C7—N6 | 118.56 (19) | O24—S23—C26 | 107.77 (11) |
N8—C7—N6 | 114.72 (19) | O25—S23—C26 | 109.78 (11) |
C9—N8—C7 | 112.93 (19) | N22—S23—C26 | 106.15 (11) |
N8—C9—N22 | 122.2 (2) | S23—C26—H26A | 109.5 |
N8—C9—C10 | 127.0 (2) | S23—C26—H26B | 109.5 |
N22—C9—C10 | 110.79 (19) | H26A—C26—H26B | 109.5 |
C11—C10—C9 | 114.5 (2) | S23—C26—H26C | 109.5 |
C11—C10—C20 | 136.4 (2) | H26A—C26—H26C | 109.5 |
C9—C10—C20 | 109.09 (18) | H26B—C26—H26C | 109.5 |
N12—C11—C10 | 121.5 (2) | O29—S27—O30 | 113.43 (10) |
N12—C11—C13 | 113.04 (19) | O29—S27—O28 | 112.91 (10) |
C10—C11—C13 | 125.4 (2) | O30—S27—O28 | 109.83 (9) |
C7—N12—C11 | 117.37 (19) | O29—S27—C31 | 106.91 (11) |
C18—C13—C14 | 114.8 (2) | O30—S27—C31 | 106.96 (11) |
C18—C13—C11 | 119.2 (2) | O28—S27—C31 | 106.35 (11) |
C14—C13—C11 | 126.0 (2) | S27—C31—H31A | 109.5 |
N15—C14—C13 | 124.7 (2) | S27—C31—H31B | 109.5 |
N15—C14—H14 | 117.6 | H31A—C31—H31B | 109.5 |
C13—C14—H14 | 117.6 | S27—C31—H31C | 109.5 |
C14—N15—C16 | 117.3 (2) | H31A—C31—H31C | 109.5 |
N19—C16—N15 | 120.0 (2) | H31B—C31—H31C | 109.5 |
N6—C1—C2—O3 | −54.4 (3) | C10—C11—C13—C18 | 175.9 (2) |
C1—C2—O3—C4 | 57.8 (2) | N12—C11—C13—C14 | 179.2 (2) |
C2—O3—C4—C5 | −59.1 (2) | C10—C11—C13—C14 | −3.3 (4) |
O3—C4—C5—N6 | 56.8 (2) | C18—C13—C14—N15 | 0.9 (3) |
C2—C1—N6—C7 | −144.2 (2) | C11—C13—C14—N15 | −179.9 (2) |
C2—C1—N6—C5 | 54.1 (2) | C13—C14—N15—C16 | 0.1 (4) |
C4—C5—N6—C7 | 142.8 (2) | C14—N15—C16—N19 | 178.7 (2) |
C4—C5—N6—C1 | −55.3 (3) | C14—N15—C16—N17 | −2.3 (3) |
C1—N6—C7—N12 | 3.9 (3) | N19—C16—N17—C18 | −177.6 (2) |
C5—N6—C7—N12 | 164.3 (2) | N15—C16—N17—C18 | 3.4 (3) |
C1—N6—C7—N8 | −176.77 (19) | C16—N17—C18—C13 | −2.3 (3) |
C5—N6—C7—N8 | −16.4 (3) | C14—C13—C18—N17 | 0.2 (3) |
N12—C7—N8—C9 | 0.7 (3) | C11—C13—C18—N17 | −179.11 (19) |
N6—C7—N8—C9 | −178.6 (2) | C11—C10—C20—C21 | −172.6 (3) |
C7—N8—C9—N22 | −179.6 (2) | C9—C10—C20—C21 | 5.5 (3) |
C7—N8—C9—C10 | −1.1 (3) | C10—C20—C21—N22 | −9.5 (2) |
N8—C9—C10—C11 | 1.1 (3) | N8—C9—N22—C21 | 170.9 (2) |
N22—C9—C10—C11 | 179.73 (19) | C10—C9—N22—C21 | −7.8 (3) |
N8—C9—C10—C20 | −177.5 (2) | N8—C9—N22—S23 | 6.1 (3) |
N22—C9—C10—C20 | 1.1 (3) | C10—C9—N22—S23 | −172.67 (16) |
C9—C10—C11—N12 | −0.6 (3) | C20—C21—N22—C9 | 10.8 (2) |
C20—C10—C11—N12 | 177.5 (2) | C20—C21—N22—S23 | 175.83 (16) |
C9—C10—C11—C13 | −177.8 (2) | C9—N22—S23—O24 | −57.8 (2) |
C20—C10—C11—C13 | 0.2 (4) | C21—N22—S23—O24 | 139.25 (19) |
N8—C7—N12—C11 | −0.3 (3) | C9—N22—S23—O25 | 174.00 (19) |
N6—C7—N12—C11 | 179.0 (2) | C21—N22—S23—O25 | 11.1 (2) |
C10—C11—N12—C7 | 0.2 (3) | C9—N22—S23—C26 | 58.0 (2) |
C13—C11—N12—C7 | 177.82 (19) | C21—N22—S23—C26 | −104.9 (2) |
N12—C11—C13—C18 | −1.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N17—H17···O28i | 0.88 | 1.80 | 2.678 (3) | 176 |
N19—H19A···O30ii | 0.88 | 2.00 | 2.850 (2) | 161 |
N19—H19B···O30i | 0.88 | 2.11 | 2.906 (3) | 150 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y−1, z+1. |
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