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In the title compound, C
23H
14ClN
3O
2S
2·C
6H
5ClO, the mean plane of the thiazolopyrimidine fragment makes dihedral angles of 64.26 (11), 77.70 (10) and 49.70 (18)° with the two attached phenyl rings and the 4-chlorophenoxy fragment. The crystal packing is stabilized by intermolecular O—H
O and intramolecular C—H
N hydrogen bonds, as well as by weak π–π stacking interactions.
Supporting information
CCDC reference: 634070
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.140
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
5-(4-Chlorophenoxy)-3,6-diphenyl-2-thioxo-2,3-dihydrothiazolo[4,5-
d]pyrimidin- 7(6
H)-one 4-chlorophenol solvate
top
Crystal data top
C23H14ClN3O2S2·C6H5ClO | Z = 2 |
Mr = 592.49 | F(000) = 608 |
Triclinic, P1 | Dx = 1.434 Mg m−3 |
a = 10.1348 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.5389 (13) Å | Cell parameters from 3766 reflections |
c = 13.6575 (15) Å | θ = 2.2–27.8° |
α = 113.048 (2)° | µ = 0.43 mm−1 |
β = 95.896 (2)° | T = 292 K |
γ = 105.972 (2)° | Block, colourless |
V = 1372.4 (3) Å3 | 0.30 × 0.30 × 0.20 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4250 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
φ and ω scans | h = −12→8 |
7829 measured reflections | k = −14→12 |
5302 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0761P)2] where P = (Fo2 + 2Fc2)/3 |
5302 reflections | (Δ/σ)max = 0.001 |
356 parameters | Δρmax = 0.35 e Å−3 |
1 restraint | Δρmin = −0.45 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S2 | 0.19892 (7) | 1.05543 (6) | 1.07799 (5) | 0.05180 (18) | |
Cl1 | 0.16603 (7) | 1.15170 (6) | 0.35219 (5) | 0.05797 (19) | |
S1 | 0.14058 (8) | 1.31175 (6) | 1.16484 (5) | 0.0607 (2) | |
Cl2 | 0.33952 (10) | 0.65670 (10) | 0.40319 (8) | 0.0971 (3) | |
O2 | 0.20147 (17) | 0.86939 (14) | 0.62438 (12) | 0.0485 (4) | |
N2 | 0.17898 (18) | 1.02628 (17) | 0.78372 (14) | 0.0409 (4) | |
N3 | 0.23295 (18) | 0.83517 (16) | 0.77446 (14) | 0.0407 (4) | |
C17 | 0.2037 (2) | 0.9164 (2) | 0.73104 (17) | 0.0399 (4) | |
N1 | 0.15915 (18) | 1.17214 (16) | 0.95743 (14) | 0.0418 (4) | |
O1 | 0.26890 (19) | 0.79254 (15) | 0.92294 (13) | 0.0577 (4) | |
C8 | 0.1828 (2) | 1.0568 (2) | 0.88960 (17) | 0.0402 (4) | |
C18 | 0.1879 (2) | 0.9443 (2) | 0.56643 (16) | 0.0395 (5) | |
C20 | 0.0916 (2) | 0.9365 (2) | 0.39652 (17) | 0.0432 (5) | |
H20 | 0.0319 | 0.8903 | 0.3267 | 0.052* | |
C21 | 0.1728 (2) | 1.0698 (2) | 0.43530 (17) | 0.0421 (5) | |
C9 | 0.2077 (2) | 0.9834 (2) | 0.94257 (17) | 0.0443 (5) | |
C22 | 0.2593 (2) | 1.1406 (2) | 0.53921 (17) | 0.0437 (5) | |
H22 | 0.3123 | 1.2308 | 0.5643 | 0.052* | |
C19 | 0.1000 (2) | 0.8726 (2) | 0.46232 (17) | 0.0439 (5) | |
H19 | 0.0472 | 0.7823 | 0.4370 | 0.053* | |
C6 | 0.1422 (2) | 1.2689 (2) | 0.91985 (17) | 0.0437 (5) | |
C23 | 0.2677 (2) | 1.0784 (2) | 0.60584 (17) | 0.0424 (5) | |
H23 | 0.3259 | 1.1256 | 0.6762 | 0.051* | |
C10 | 0.2382 (2) | 0.8647 (2) | 0.88544 (17) | 0.0439 (5) | |
C11 | 0.2714 (2) | 0.7205 (2) | 0.70932 (17) | 0.0432 (5) | |
C7 | 0.1628 (2) | 1.1874 (2) | 1.06322 (18) | 0.0454 (5) | |
C14 | 0.3483 (4) | 0.5086 (3) | 0.5871 (2) | 0.0695 (8) | |
H14 | 0.3744 | 0.4371 | 0.5446 | 0.083* | |
C16 | 0.1681 (3) | 0.6027 (2) | 0.6344 (2) | 0.0577 (6) | |
H16 | 0.0733 | 0.5947 | 0.6254 | 0.069* | |
C28 | 0.4172 (3) | 0.9327 (3) | 0.2913 (2) | 0.0614 (6) | |
H28 | 0.4334 | 1.0242 | 0.3189 | 0.074* | |
C29 | 0.3922 (3) | 0.8685 (3) | 0.3568 (2) | 0.0624 (7) | |
H29 | 0.3904 | 0.9167 | 0.4292 | 0.075* | |
C12 | 0.4108 (3) | 0.7322 (2) | 0.7251 (2) | 0.0553 (6) | |
H12 | 0.4793 | 0.8117 | 0.7770 | 0.066* | |
C1 | 0.2524 (3) | 1.3344 (3) | 0.8879 (2) | 0.0653 (7) | |
H1 | 0.3373 | 1.3182 | 0.8922 | 0.078* | |
C5 | 0.0170 (3) | 1.2932 (2) | 0.9143 (2) | 0.0571 (6) | |
H5 | −0.0571 | 1.2482 | 0.9355 | 0.069* | |
C27 | 0.4180 (2) | 0.8595 (2) | 0.1834 (2) | 0.0548 (6) | |
C26 | 0.3946 (3) | 0.7242 (3) | 0.1419 (2) | 0.0633 (7) | |
H26 | 0.3946 | 0.6757 | 0.0692 | 0.076* | |
C15 | 0.2087 (4) | 0.4961 (2) | 0.5726 (2) | 0.0704 (8) | |
H15 | 0.1407 | 0.4159 | 0.5213 | 0.084* | |
C24 | 0.3699 (3) | 0.7338 (3) | 0.3166 (2) | 0.0605 (6) | |
C2 | 0.2342 (4) | 1.4245 (3) | 0.8494 (3) | 0.0848 (9) | |
H2 | 0.3069 | 1.4685 | 0.8265 | 0.102* | |
C13 | 0.4494 (3) | 0.6244 (3) | 0.6628 (3) | 0.0708 (8) | |
H13 | 0.5439 | 0.6313 | 0.6729 | 0.085* | |
C3 | 0.1106 (4) | 1.4495 (3) | 0.8447 (3) | 0.0842 (10) | |
H3 | 0.0998 | 1.5110 | 0.8192 | 0.101* | |
C4 | 0.0023 (4) | 1.3848 (3) | 0.8772 (3) | 0.0766 (8) | |
H4 | −0.0816 | 1.4028 | 0.8741 | 0.092* | |
C25 | 0.3709 (3) | 0.6600 (3) | 0.2099 (2) | 0.0692 (7) | |
H25 | 0.3561 | 0.5687 | 0.1833 | 0.083* | |
O3 | 0.4481 (2) | 0.9279 (2) | 0.12121 (19) | 0.0788 (6) | |
H3A | 0.413 (5) | 0.880 (3) | 0.0550 (11) | 0.145 (18)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S2 | 0.0777 (4) | 0.0483 (3) | 0.0374 (3) | 0.0255 (3) | 0.0180 (3) | 0.0231 (2) |
Cl1 | 0.0773 (4) | 0.0627 (4) | 0.0472 (3) | 0.0260 (3) | 0.0167 (3) | 0.0355 (3) |
S1 | 0.0915 (5) | 0.0509 (4) | 0.0438 (3) | 0.0307 (3) | 0.0273 (3) | 0.0179 (3) |
Cl2 | 0.1132 (7) | 0.1155 (7) | 0.0947 (6) | 0.0395 (5) | 0.0438 (5) | 0.0730 (6) |
O2 | 0.0767 (10) | 0.0463 (8) | 0.0375 (8) | 0.0338 (8) | 0.0207 (7) | 0.0230 (7) |
N2 | 0.0551 (10) | 0.0400 (9) | 0.0366 (9) | 0.0231 (8) | 0.0152 (8) | 0.0201 (7) |
N3 | 0.0532 (10) | 0.0367 (9) | 0.0381 (9) | 0.0186 (8) | 0.0107 (8) | 0.0201 (8) |
C17 | 0.0482 (11) | 0.0396 (10) | 0.0383 (11) | 0.0182 (9) | 0.0127 (9) | 0.0207 (9) |
N1 | 0.0543 (10) | 0.0388 (9) | 0.0372 (9) | 0.0195 (8) | 0.0154 (8) | 0.0180 (7) |
O1 | 0.0910 (12) | 0.0493 (9) | 0.0465 (9) | 0.0328 (8) | 0.0130 (8) | 0.0294 (8) |
C8 | 0.0474 (11) | 0.0364 (10) | 0.0377 (11) | 0.0144 (9) | 0.0112 (9) | 0.0170 (9) |
C18 | 0.0495 (12) | 0.0464 (11) | 0.0365 (10) | 0.0273 (9) | 0.0181 (9) | 0.0229 (9) |
C20 | 0.0498 (12) | 0.0483 (12) | 0.0316 (10) | 0.0187 (9) | 0.0105 (9) | 0.0161 (9) |
C21 | 0.0503 (12) | 0.0484 (12) | 0.0412 (11) | 0.0254 (10) | 0.0185 (9) | 0.0256 (10) |
C9 | 0.0578 (13) | 0.0431 (11) | 0.0355 (11) | 0.0182 (10) | 0.0122 (9) | 0.0198 (9) |
C22 | 0.0487 (12) | 0.0425 (11) | 0.0431 (12) | 0.0142 (9) | 0.0134 (9) | 0.0223 (9) |
C19 | 0.0517 (12) | 0.0399 (11) | 0.0404 (11) | 0.0187 (9) | 0.0148 (9) | 0.0149 (9) |
C6 | 0.0600 (13) | 0.0371 (10) | 0.0381 (11) | 0.0200 (9) | 0.0168 (9) | 0.0172 (9) |
C23 | 0.0446 (11) | 0.0458 (11) | 0.0373 (11) | 0.0180 (9) | 0.0081 (9) | 0.0177 (9) |
C10 | 0.0559 (13) | 0.0384 (11) | 0.0391 (11) | 0.0152 (9) | 0.0101 (9) | 0.0196 (9) |
C11 | 0.0617 (14) | 0.0343 (10) | 0.0401 (11) | 0.0198 (9) | 0.0138 (10) | 0.0201 (9) |
C7 | 0.0543 (13) | 0.0422 (11) | 0.0412 (11) | 0.0148 (9) | 0.0163 (9) | 0.0199 (9) |
C14 | 0.108 (2) | 0.0500 (15) | 0.0765 (19) | 0.0433 (15) | 0.0446 (17) | 0.0368 (14) |
C16 | 0.0672 (15) | 0.0438 (13) | 0.0572 (15) | 0.0157 (11) | 0.0119 (12) | 0.0202 (11) |
C28 | 0.0560 (14) | 0.0596 (15) | 0.0695 (17) | 0.0266 (12) | 0.0113 (12) | 0.0256 (13) |
C29 | 0.0531 (14) | 0.0753 (17) | 0.0594 (16) | 0.0269 (12) | 0.0196 (12) | 0.0253 (14) |
C12 | 0.0597 (15) | 0.0469 (13) | 0.0632 (15) | 0.0222 (11) | 0.0164 (12) | 0.0251 (12) |
C1 | 0.0805 (18) | 0.0556 (14) | 0.0756 (18) | 0.0279 (13) | 0.0371 (15) | 0.0370 (14) |
C5 | 0.0663 (15) | 0.0523 (13) | 0.0574 (15) | 0.0273 (12) | 0.0161 (12) | 0.0238 (12) |
C27 | 0.0485 (13) | 0.0582 (14) | 0.0563 (14) | 0.0167 (11) | 0.0030 (11) | 0.0273 (12) |
C26 | 0.0692 (16) | 0.0601 (15) | 0.0490 (14) | 0.0158 (12) | 0.0092 (12) | 0.0181 (12) |
C15 | 0.103 (2) | 0.0389 (13) | 0.0620 (17) | 0.0190 (13) | 0.0189 (15) | 0.0185 (12) |
C24 | 0.0570 (15) | 0.0722 (17) | 0.0625 (16) | 0.0230 (12) | 0.0192 (12) | 0.0378 (14) |
C2 | 0.129 (3) | 0.0631 (18) | 0.083 (2) | 0.0315 (18) | 0.051 (2) | 0.0478 (17) |
C13 | 0.0803 (18) | 0.0656 (17) | 0.089 (2) | 0.0422 (15) | 0.0370 (16) | 0.0411 (16) |
C3 | 0.146 (3) | 0.0599 (17) | 0.0658 (19) | 0.051 (2) | 0.0288 (19) | 0.0354 (15) |
C4 | 0.099 (2) | 0.0672 (17) | 0.0721 (19) | 0.0479 (16) | 0.0100 (16) | 0.0288 (15) |
C25 | 0.0768 (18) | 0.0552 (15) | 0.0718 (18) | 0.0158 (13) | 0.0234 (14) | 0.0274 (14) |
O3 | 0.0941 (15) | 0.0707 (13) | 0.0658 (13) | 0.0159 (11) | 0.0032 (11) | 0.0365 (11) |
Geometric parameters (Å, º) top
S2—C9 | 1.729 (2) | C11—C16 | 1.378 (3) |
S2—C7 | 1.739 (2) | C14—C13 | 1.361 (4) |
Cl1—C21 | 1.745 (2) | C14—C15 | 1.367 (4) |
S1—C7 | 1.649 (2) | C14—H14 | 0.9300 |
Cl2—C24 | 1.741 (3) | C16—C15 | 1.390 (4) |
O2—C17 | 1.336 (2) | C16—H16 | 0.9300 |
O2—C18 | 1.404 (2) | C28—C29 | 1.370 (4) |
N2—C17 | 1.299 (3) | C28—C27 | 1.384 (4) |
N2—C8 | 1.341 (3) | C28—H28 | 0.9300 |
N3—C17 | 1.367 (2) | C29—C24 | 1.372 (4) |
N3—C10 | 1.409 (3) | C29—H29 | 0.9300 |
N3—C11 | 1.458 (3) | C12—C13 | 1.390 (3) |
N1—C7 | 1.381 (3) | C12—H12 | 0.9300 |
N1—C8 | 1.394 (3) | C1—C2 | 1.381 (4) |
N1—C6 | 1.441 (3) | C1—H1 | 0.9300 |
O1—C10 | 1.224 (2) | C5—C4 | 1.373 (4) |
C8—C9 | 1.365 (3) | C5—H5 | 0.9300 |
C18—C23 | 1.381 (3) | C27—O3 | 1.371 (3) |
C18—C19 | 1.383 (3) | C27—C26 | 1.376 (3) |
C20—C19 | 1.377 (3) | C26—C25 | 1.399 (4) |
C20—C21 | 1.378 (3) | C26—H26 | 0.9300 |
C20—H20 | 0.9300 | C15—H15 | 0.9300 |
C21—C22 | 1.376 (3) | C24—C25 | 1.373 (4) |
C9—C10 | 1.423 (3) | C2—C3 | 1.361 (5) |
C22—C23 | 1.370 (3) | C2—H2 | 0.9300 |
C22—H22 | 0.9300 | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | C3—C4 | 1.367 (5) |
C6—C5 | 1.374 (3) | C3—H3 | 0.9300 |
C6—C1 | 1.380 (3) | C4—H4 | 0.9300 |
C23—H23 | 0.9300 | C25—H25 | 0.9300 |
C11—C12 | 1.368 (3) | O3—H3A | 0.827 (9) |
| | | |
C9—S2—C7 | 91.45 (10) | C13—C14—H14 | 119.6 |
C17—O2—C18 | 121.33 (15) | C15—C14—H14 | 119.6 |
C17—N2—C8 | 113.87 (17) | C11—C16—C15 | 118.6 (2) |
C17—N3—C10 | 121.56 (17) | C11—C16—H16 | 120.7 |
C17—N3—C11 | 120.76 (17) | C15—C16—H16 | 120.7 |
C10—N3—C11 | 117.49 (16) | C29—C28—C27 | 119.2 (2) |
N2—C17—O2 | 121.99 (17) | C29—C28—H28 | 120.4 |
N2—C17—N3 | 125.90 (19) | C27—C28—H28 | 120.4 |
O2—C17—N3 | 112.11 (16) | C28—C29—C24 | 120.5 (3) |
C7—N1—C8 | 113.81 (17) | C28—C29—H29 | 119.7 |
C7—N1—C6 | 124.39 (17) | C24—C29—H29 | 119.7 |
C8—N1—C6 | 121.68 (17) | C11—C12—C13 | 119.5 (2) |
N2—C8—C9 | 126.23 (19) | C11—C12—H12 | 120.3 |
N2—C8—N1 | 120.83 (18) | C13—C12—H12 | 120.3 |
C9—C8—N1 | 112.93 (18) | C6—C1—C2 | 118.6 (3) |
C23—C18—C19 | 121.53 (19) | C6—C1—H1 | 120.7 |
C23—C18—O2 | 122.35 (18) | C2—C1—H1 | 120.7 |
C19—C18—O2 | 115.82 (18) | C4—C5—C6 | 119.3 (3) |
C19—C20—C21 | 119.21 (19) | C4—C5—H5 | 120.3 |
C19—C20—H20 | 120.4 | C6—C5—H5 | 120.3 |
C21—C20—H20 | 120.4 | O3—C27—C26 | 121.6 (2) |
C22—C21—C20 | 121.15 (19) | O3—C27—C28 | 117.6 (2) |
C22—C21—Cl1 | 118.97 (17) | C26—C27—C28 | 120.8 (2) |
C20—C21—Cl1 | 119.88 (16) | C27—C26—C25 | 119.6 (3) |
C8—C9—C10 | 119.83 (19) | C27—C26—H26 | 120.2 |
C8—C9—S2 | 111.64 (16) | C25—C26—H26 | 120.2 |
C10—C9—S2 | 128.53 (16) | C14—C15—C16 | 120.2 (3) |
C23—C22—C21 | 120.2 (2) | C14—C15—H15 | 119.9 |
C23—C22—H22 | 119.9 | C16—C15—H15 | 119.9 |
C21—C22—H22 | 119.9 | C29—C24—C25 | 121.0 (2) |
C20—C19—C18 | 119.23 (19) | C29—C24—Cl2 | 118.9 (2) |
C20—C19—H19 | 120.4 | C25—C24—Cl2 | 120.1 (2) |
C18—C19—H19 | 120.4 | C3—C2—C1 | 120.5 (3) |
C5—C6—C1 | 120.9 (2) | C3—C2—H2 | 119.7 |
C5—C6—N1 | 120.2 (2) | C1—C2—H2 | 119.7 |
C1—C6—N1 | 119.0 (2) | C14—C13—C12 | 119.7 (3) |
C22—C23—C18 | 118.67 (19) | C14—C13—H13 | 120.1 |
C22—C23—H23 | 120.7 | C12—C13—H13 | 120.1 |
C18—C23—H23 | 120.7 | C2—C3—C4 | 120.4 (3) |
O1—C10—N3 | 120.16 (19) | C2—C3—H3 | 119.8 |
O1—C10—C9 | 127.3 (2) | C4—C3—H3 | 119.8 |
N3—C10—C9 | 112.56 (17) | C3—C4—C5 | 120.2 (3) |
C12—C11—C16 | 121.2 (2) | C3—C4—H4 | 119.9 |
C12—C11—N3 | 118.74 (19) | C5—C4—H4 | 119.9 |
C16—C11—N3 | 120.1 (2) | C24—C25—C26 | 118.9 (3) |
N1—C7—S1 | 126.88 (16) | C24—C25—H25 | 120.5 |
N1—C7—S2 | 110.15 (15) | C26—C25—H25 | 120.5 |
S1—C7—S2 | 122.95 (13) | C27—O3—H3A | 113 (3) |
C13—C14—C15 | 120.8 (2) | | |
| | | |
C8—N2—C17—O2 | 178.71 (18) | C8—C9—C10—O1 | 176.4 (2) |
C8—N2—C17—N3 | −0.6 (3) | S2—C9—C10—O1 | −2.6 (4) |
C18—O2—C17—N2 | 7.3 (3) | C8—C9—C10—N3 | −2.3 (3) |
C18—O2—C17—N3 | −173.33 (17) | S2—C9—C10—N3 | 178.69 (16) |
C10—N3—C17—N2 | 0.4 (3) | C17—N3—C11—C12 | 101.0 (2) |
C11—N3—C17—N2 | −174.46 (19) | C10—N3—C11—C12 | −74.1 (3) |
C10—N3—C17—O2 | −178.94 (17) | C17—N3—C11—C16 | −79.7 (3) |
C11—N3—C17—O2 | 6.2 (3) | C10—N3—C11—C16 | 105.2 (2) |
C17—N2—C8—C9 | −0.9 (3) | C8—N1—C7—S1 | 179.51 (16) |
C17—N2—C8—N1 | 179.66 (18) | C6—N1—C7—S1 | 3.5 (3) |
C7—N1—C8—N2 | 178.30 (18) | C8—N1—C7—S2 | 0.8 (2) |
C6—N1—C8—N2 | −5.6 (3) | C6—N1—C7—S2 | −175.22 (16) |
C7—N1—C8—C9 | −1.2 (3) | C9—S2—C7—N1 | −0.14 (16) |
C6—N1—C8—C9 | 174.90 (18) | C9—S2—C7—S1 | −178.93 (16) |
C17—O2—C18—C23 | 47.2 (3) | C12—C11—C16—C15 | −1.6 (4) |
C17—O2—C18—C19 | −139.1 (2) | N3—C11—C16—C15 | 179.1 (2) |
C19—C20—C21—C22 | −1.5 (3) | C27—C28—C29—C24 | 0.7 (4) |
C19—C20—C21—Cl1 | 178.82 (16) | C16—C11—C12—C13 | 1.4 (4) |
N2—C8—C9—C10 | 2.5 (3) | N3—C11—C12—C13 | −179.3 (2) |
N1—C8—C9—C10 | −178.05 (19) | C5—C6—C1—C2 | −0.4 (4) |
N2—C8—C9—S2 | −178.40 (17) | N1—C6—C1—C2 | 178.4 (2) |
N1—C8—C9—S2 | 1.1 (2) | C1—C6—C5—C4 | −0.5 (4) |
C7—S2—C9—C8 | −0.54 (17) | N1—C6—C5—C4 | −179.3 (2) |
C7—S2—C9—C10 | 178.5 (2) | C29—C28—C27—O3 | −177.8 (2) |
C20—C21—C22—C23 | 0.9 (3) | C29—C28—C27—C26 | −0.2 (4) |
Cl1—C21—C22—C23 | −179.38 (16) | O3—C27—C26—C25 | 177.0 (2) |
C21—C20—C19—C18 | 1.1 (3) | C28—C27—C26—C25 | −0.5 (4) |
C23—C18—C19—C20 | −0.1 (3) | C13—C14—C15—C16 | 0.9 (4) |
O2—C18—C19—C20 | −173.95 (18) | C11—C16—C15—C14 | 0.4 (4) |
C7—N1—C6—C5 | −67.2 (3) | C28—C29—C24—C25 | −0.5 (4) |
C8—N1—C6—C5 | 117.1 (2) | C28—C29—C24—Cl2 | 179.65 (19) |
C7—N1—C6—C1 | 114.0 (3) | C6—C1—C2—C3 | 1.0 (5) |
C8—N1—C6—C1 | −61.7 (3) | C15—C14—C13—C12 | −1.2 (4) |
C21—C22—C23—C18 | 0.1 (3) | C11—C12—C13—C14 | 0.0 (4) |
C19—C18—C23—C22 | −0.4 (3) | C1—C2—C3—C4 | −0.6 (5) |
O2—C18—C23—C22 | 172.98 (18) | C2—C3—C4—C5 | −0.4 (5) |
C17—N3—C10—O1 | −177.74 (19) | C6—C5—C4—C3 | 0.9 (4) |
C11—N3—C10—O1 | −2.7 (3) | C29—C24—C25—C26 | −0.3 (4) |
C17—N3—C10—C9 | 1.1 (3) | Cl2—C24—C25—C26 | 179.6 (2) |
C11—N3—C10—C9 | 176.11 (18) | C27—C26—C25—C24 | 0.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···N2 | 0.93 | 2.55 | 2.893 (3) | 102 |
O3—H3A···O1i | 0.83 (1) | 1.90 (2) | 2.681 (3) | 156 (4) |
Symmetry code: (i) x, y, z−1. |
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