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The title compound, C
29H
26N
4O
5S, is based on an almost planar pyrazolo[3,4-
d]pyrimidin-4-one core. Molecules are packed through weak intermolecular C—H
O and C—H
N interactions.
Supporting information
CCDC reference: 632397
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.008 Å
- R factor = 0.063
- wR factor = 0.185
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.41 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.07 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for O5 - C27 .. 7.92 su
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.131
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.07 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _reflns_number_total 5408
Count of symmetry unique reflns 2843
Completeness (_total/calc) 190.22%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2565
Fraction of Friedel pairs measured 0.902
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.
Ethyl {4-[5-(3-methylphenyl)-3-methylsulfanyl-4-oxo-1-
phenylpyrazolo[3,4-
d]pyrimidin-6-yloxy]phenoxy}acetate
top
Crystal data top
C29H26N4O5S | Dx = 1.301 Mg m−3 |
Mr = 542.60 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 6550 reflections |
Hall symbol: P 4w | θ = 2.5–21.2° |
a = 14.1908 (16) Å | µ = 0.16 mm−1 |
c = 13.760 (3) Å | T = 292 K |
V = 2771.0 (8) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.20 × 0.04 mm |
F(000) = 1136 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5408 independent reflections |
Radiation source: fine-focus sealed tube | 3258 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.131 |
φ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −17→17 |
Tmin = 0.953, Tmax = 0.987 | k = −17→17 |
27946 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.12P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
5408 reflections | Δρmax = 0.58 e Å−3 |
356 parameters | Δρmin = −0.31 e Å−3 |
32 restraints | Absolute structure: Flack (1983), 2572 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.11 (13) |
Special details top
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz) 7.91 (d, 2H, Ar), 7.43 (t,
1H, Ar), 7.15–7.34 (m, 6H, Ar), 7.10 (d, 2H, OC6H4O), 6.94 (d, 2H,
OC6H4O), 4.64 (s, 2H, OCH2C═O), 4.28 (q, 2H, OCH2), 2.67 (s, 3H,
SCH3), 1.30 (t, 3H, OCH2CH3); EI—MS (70 eV, m/z): 542
(M+), 543 (M+ + 1). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.3978 (3) | 0.4015 (3) | 0.1932 (3) | 0.0561 (10) | |
C2 | 0.3289 (3) | 0.4678 (3) | 0.1797 (4) | 0.0737 (11) | |
H2 | 0.3445 | 0.5300 | 0.1662 | 0.088* | |
C3 | 0.2356 (3) | 0.4405 (4) | 0.1865 (5) | 0.0880 (15) | |
H3 | 0.1886 | 0.4854 | 0.1781 | 0.106* | |
C4 | 0.2108 (4) | 0.3497 (4) | 0.2052 (4) | 0.0853 (15) | |
H4 | 0.1477 | 0.3327 | 0.2111 | 0.102* | |
C5 | 0.2809 (4) | 0.2834 (4) | 0.2154 (4) | 0.0879 (15) | |
H5 | 0.2649 | 0.2209 | 0.2268 | 0.106* | |
C6 | 0.3741 (3) | 0.3080 (4) | 0.2090 (4) | 0.0774 (13) | |
H6 | 0.4208 | 0.2625 | 0.2151 | 0.093* | |
C7 | 0.6062 (3) | 0.5319 (3) | 0.1794 (3) | 0.0569 (9) | |
C8 | 0.6486 (3) | 0.4423 (3) | 0.1795 (3) | 0.0525 (9) | |
C9 | 0.5747 (3) | 0.3799 (3) | 0.1840 (3) | 0.0553 (9) | |
C10 | 0.5667 (4) | 0.7194 (3) | 0.1725 (4) | 0.0841 (14) | |
H10A | 0.5240 | 0.7024 | 0.1212 | 0.126* | |
H10B | 0.5886 | 0.7826 | 0.1625 | 0.126* | |
H10C | 0.5347 | 0.7154 | 0.2338 | 0.126* | |
C11 | 0.7433 (3) | 0.4079 (3) | 0.1716 (3) | 0.0538 (9) | |
C12 | 0.6656 (3) | 0.2533 (3) | 0.1778 (3) | 0.0585 (9) | |
C13 | 0.8362 (3) | 0.2617 (3) | 0.1623 (3) | 0.0629 (10) | |
C14 | 0.8641 (4) | 0.2286 (4) | 0.0732 (4) | 0.0828 (14) | |
H14 | 0.8250 | 0.2354 | 0.0195 | 0.099* | |
C15 | 0.9517 (4) | 0.1846 (4) | 0.0638 (5) | 0.0930 (17) | |
C16 | 1.0100 (4) | 0.1753 (4) | 0.1431 (6) | 0.0973 (19) | |
H16 | 1.0691 | 0.1479 | 0.1359 | 0.117* | |
C17 | 0.9816 (4) | 0.2059 (5) | 0.2311 (6) | 0.104 (2) | |
H17 | 1.0204 | 0.1974 | 0.2849 | 0.125* | |
C18 | 0.8939 (3) | 0.2505 (4) | 0.2421 (4) | 0.0842 (14) | |
H18 | 0.8749 | 0.2722 | 0.3028 | 0.101* | |
C19 | 0.9787 (6) | 0.1461 (6) | −0.0332 (6) | 0.154 (3) | |
H19A | 1.0447 | 0.1563 | −0.0440 | 0.232* | |
H19B | 0.9431 | 0.1775 | −0.0830 | 0.232* | |
H19C | 0.9655 | 0.0798 | −0.0351 | 0.232* | |
C20 | 0.6056 (3) | 0.0995 (3) | 0.1738 (4) | 0.0613 (10) | |
C21 | 0.5877 (3) | 0.0453 (3) | 0.2539 (3) | 0.0717 (12) | |
H21 | 0.6255 | 0.0509 | 0.3088 | 0.086* | |
C22 | 0.5140 (4) | −0.0172 (3) | 0.2532 (3) | 0.0731 (13) | |
H22 | 0.5011 | −0.0536 | 0.3078 | 0.088* | |
C23 | 0.4597 (3) | −0.0255 (3) | 0.1716 (4) | 0.0659 (10) | |
C24 | 0.4777 (4) | 0.0270 (4) | 0.0918 (4) | 0.0798 (14) | |
H24 | 0.4399 | 0.0208 | 0.0369 | 0.096* | |
C25 | 0.5523 (3) | 0.0900 (3) | 0.0912 (3) | 0.0708 (12) | |
H25 | 0.5659 | 0.1252 | 0.0360 | 0.085* | |
C26 | 0.3469 (5) | −0.1262 (4) | 0.2463 (6) | 0.115 (2) | |
H26A | 0.3962 | −0.1529 | 0.2866 | 0.138* | |
H26B | 0.3023 | −0.1754 | 0.2298 | 0.138* | |
C27 | 0.2943 (6) | −0.0405 (8) | 0.3026 (8) | 0.146 (3) | |
C28 | 0.2346 (9) | 0.0121 (10) | 0.4499 (10) | 0.202 (5) | |
H28A | 0.2176 | −0.0166 | 0.5114 | 0.242* | |
H28B | 0.1769 | 0.0327 | 0.4186 | 0.242* | |
C29 | 0.2984 (11) | 0.1004 (9) | 0.4700 (13) | 0.231 (6) | |
H29A | 0.3546 | 0.0809 | 0.5031 | 0.346* | |
H29B | 0.2646 | 0.1446 | 0.5096 | 0.346* | |
H29C | 0.3150 | 0.1296 | 0.4094 | 0.346* | |
N1 | 0.4943 (2) | 0.4300 (2) | 0.1883 (2) | 0.0564 (8) | |
N2 | 0.5141 (2) | 0.5264 (2) | 0.1854 (2) | 0.0577 (8) | |
N3 | 0.7462 (2) | 0.3064 (2) | 0.1718 (3) | 0.0582 (8) | |
N4 | 0.5805 (2) | 0.2832 (2) | 0.1849 (2) | 0.0580 (8) | |
O1 | 0.81497 (19) | 0.45220 (19) | 0.1628 (2) | 0.0665 (7) | |
O2 | 0.68416 (19) | 0.16068 (19) | 0.1759 (3) | 0.0733 (8) | |
O3 | 0.3846 (3) | −0.0868 (3) | 0.1633 (3) | 0.0970 (11) | |
O4 | 0.2606 (6) | 0.0258 (6) | 0.2576 (7) | 0.204 (3) | |
O5 | 0.2822 (5) | −0.0622 (6) | 0.3857 (7) | 0.199 (3) | |
S1 | 0.66485 (8) | 0.64038 (7) | 0.17232 (9) | 0.0729 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.055 (2) | 0.068 (3) | 0.045 (2) | −0.001 (2) | 0.0067 (16) | −0.0044 (17) |
C2 | 0.074 (3) | 0.073 (3) | 0.075 (3) | 0.007 (2) | −0.003 (2) | 0.000 (3) |
C3 | 0.061 (3) | 0.098 (4) | 0.105 (4) | 0.010 (3) | −0.005 (3) | −0.008 (3) |
C4 | 0.062 (3) | 0.106 (4) | 0.088 (4) | −0.005 (3) | 0.002 (2) | −0.008 (3) |
C5 | 0.069 (3) | 0.089 (3) | 0.106 (4) | −0.014 (3) | 0.013 (3) | 0.004 (3) |
C6 | 0.062 (3) | 0.074 (3) | 0.096 (3) | 0.001 (2) | 0.013 (2) | 0.007 (2) |
C7 | 0.072 (3) | 0.059 (2) | 0.0397 (19) | −0.0039 (19) | 0.005 (2) | −0.0020 (19) |
C8 | 0.056 (2) | 0.056 (2) | 0.0451 (19) | −0.0021 (17) | 0.0039 (18) | −0.0018 (19) |
C9 | 0.066 (2) | 0.053 (2) | 0.047 (2) | 0.0000 (19) | 0.0074 (18) | −0.0042 (19) |
C10 | 0.113 (4) | 0.068 (3) | 0.072 (3) | 0.009 (2) | −0.011 (3) | −0.004 (3) |
C11 | 0.059 (2) | 0.057 (2) | 0.0447 (18) | −0.0079 (18) | 0.0038 (19) | −0.0007 (19) |
C12 | 0.057 (2) | 0.059 (2) | 0.059 (2) | −0.0003 (19) | 0.006 (2) | 0.004 (2) |
C13 | 0.052 (2) | 0.064 (2) | 0.072 (3) | −0.0058 (18) | 0.009 (2) | 0.003 (2) |
C14 | 0.070 (3) | 0.082 (3) | 0.095 (4) | 0.008 (3) | 0.001 (3) | −0.004 (3) |
C15 | 0.072 (3) | 0.071 (3) | 0.135 (5) | 0.004 (3) | 0.029 (4) | −0.016 (3) |
C16 | 0.055 (3) | 0.077 (3) | 0.159 (7) | −0.006 (3) | 0.000 (4) | −0.002 (4) |
C17 | 0.065 (4) | 0.117 (5) | 0.129 (6) | −0.005 (3) | −0.018 (4) | 0.034 (4) |
C18 | 0.066 (3) | 0.105 (4) | 0.081 (3) | −0.003 (3) | −0.010 (3) | 0.012 (3) |
C19 | 0.143 (7) | 0.145 (7) | 0.175 (8) | 0.017 (5) | 0.036 (6) | −0.038 (6) |
C20 | 0.058 (2) | 0.045 (2) | 0.080 (3) | 0.0056 (17) | 0.007 (2) | 0.002 (2) |
C21 | 0.077 (3) | 0.070 (3) | 0.069 (3) | −0.004 (2) | −0.010 (2) | 0.003 (2) |
C22 | 0.081 (3) | 0.066 (3) | 0.072 (3) | −0.001 (3) | 0.007 (3) | 0.014 (2) |
C23 | 0.066 (2) | 0.053 (2) | 0.079 (3) | −0.0106 (18) | 0.000 (3) | −0.002 (2) |
C24 | 0.087 (3) | 0.074 (3) | 0.078 (3) | −0.007 (3) | −0.019 (3) | 0.001 (3) |
C25 | 0.072 (3) | 0.071 (3) | 0.069 (3) | −0.008 (2) | −0.005 (2) | 0.018 (2) |
C26 | 0.095 (4) | 0.085 (4) | 0.165 (7) | −0.023 (3) | 0.009 (4) | 0.030 (4) |
C27 | 0.107 (5) | 0.176 (7) | 0.155 (7) | 0.014 (5) | 0.024 (5) | 0.051 (6) |
C28 | 0.186 (8) | 0.211 (8) | 0.208 (8) | 0.008 (7) | 0.015 (7) | −0.022 (7) |
C29 | 0.248 (12) | 0.195 (10) | 0.249 (13) | 0.039 (10) | −0.037 (11) | −0.003 (9) |
N1 | 0.061 (2) | 0.0546 (19) | 0.0539 (19) | 0.0019 (15) | 0.0066 (15) | 0.0008 (15) |
N2 | 0.063 (2) | 0.057 (2) | 0.0536 (19) | 0.0020 (15) | 0.0099 (16) | −0.0009 (16) |
N3 | 0.0488 (17) | 0.0638 (19) | 0.0621 (18) | −0.0009 (14) | 0.0012 (16) | 0.0004 (18) |
N4 | 0.0539 (19) | 0.0558 (18) | 0.064 (2) | 0.0002 (14) | 0.0060 (16) | 0.0006 (17) |
O1 | 0.0600 (17) | 0.0697 (17) | 0.0699 (17) | −0.0114 (13) | 0.0026 (15) | −0.0015 (15) |
O2 | 0.0556 (16) | 0.0546 (16) | 0.110 (2) | −0.0013 (12) | −0.0018 (17) | 0.0088 (18) |
O3 | 0.095 (2) | 0.084 (2) | 0.111 (3) | −0.0282 (19) | −0.013 (2) | 0.004 (2) |
O4 | 0.191 (6) | 0.197 (6) | 0.225 (8) | 0.053 (6) | 0.012 (6) | 0.031 (6) |
O5 | 0.175 (5) | 0.217 (6) | 0.206 (7) | 0.053 (5) | 0.011 (5) | 0.027 (5) |
S1 | 0.0852 (8) | 0.0596 (6) | 0.0739 (7) | −0.0087 (5) | 0.0069 (6) | −0.0040 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.370 (6) | C16—C17 | 1.349 (10) |
C1—C6 | 1.385 (6) | C16—H16 | 0.9300 |
C1—N1 | 1.430 (5) | C17—C18 | 1.404 (9) |
C2—C3 | 1.382 (7) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.361 (7) | C19—H19A | 0.9600 |
C3—H3 | 0.9300 | C19—H19B | 0.9600 |
C4—C5 | 1.376 (8) | C19—H19C | 0.9600 |
C4—H4 | 0.9300 | C20—C21 | 1.367 (7) |
C5—C6 | 1.370 (7) | C20—C25 | 1.371 (7) |
C5—H5 | 0.9300 | C20—O2 | 1.414 (5) |
C6—H6 | 0.9300 | C21—C22 | 1.371 (7) |
C7—N2 | 1.313 (5) | C21—H21 | 0.9300 |
C7—C8 | 1.406 (5) | C22—C23 | 1.367 (7) |
C7—S1 | 1.752 (4) | C22—H22 | 0.9300 |
C8—C9 | 1.374 (5) | C23—C24 | 1.352 (7) |
C8—C11 | 1.433 (5) | C23—O3 | 1.380 (5) |
C9—N1 | 1.345 (5) | C24—C25 | 1.386 (7) |
C9—N4 | 1.375 (5) | C24—H24 | 0.9300 |
C10—S1 | 1.788 (5) | C25—H25 | 0.9300 |
C10—H10A | 0.9600 | C26—O3 | 1.379 (8) |
C10—H10B | 0.9600 | C26—C27 | 1.623 (13) |
C10—H10C | 0.9600 | C26—H26A | 0.9700 |
C11—O1 | 1.202 (4) | C26—H26B | 0.9700 |
C11—N3 | 1.442 (5) | C27—O5 | 1.197 (11) |
C12—N4 | 1.284 (5) | C27—O4 | 1.224 (11) |
C12—O2 | 1.341 (5) | C28—O5 | 1.533 (14) |
C12—N3 | 1.372 (5) | C28—C29 | 1.571 (18) |
C13—C14 | 1.370 (7) | C28—H28A | 0.9700 |
C13—C18 | 1.380 (7) | C28—H28B | 0.9700 |
C13—N3 | 1.432 (5) | C29—H29A | 0.9600 |
C14—C15 | 1.397 (7) | C29—H29B | 0.9600 |
C14—H14 | 0.9300 | C29—H29C | 0.9600 |
C15—C16 | 1.376 (9) | N1—N2 | 1.397 (4) |
C15—C19 | 1.492 (7) | | |
| | | |
C2—C1—C6 | 120.3 (4) | C17—C18—H18 | 120.2 |
C2—C1—N1 | 118.9 (4) | C15—C19—H19A | 109.5 |
C6—C1—N1 | 120.8 (4) | C15—C19—H19B | 109.5 |
C1—C2—C3 | 118.8 (5) | C15—C19—H19C | 109.5 |
C1—C2—H2 | 120.6 | C21—C20—C25 | 120.7 (4) |
C3—C2—H2 | 120.6 | C21—C20—O2 | 118.4 (4) |
C4—C3—C2 | 121.8 (5) | C25—C20—O2 | 120.8 (4) |
C4—C3—H3 | 119.1 | C20—C21—C22 | 119.9 (4) |
C2—C3—H3 | 119.1 | C20—C21—H21 | 120.0 |
C3—C4—C5 | 118.6 (5) | C22—C21—H21 | 120.0 |
C3—C4—H4 | 120.7 | C23—C22—C21 | 119.5 (4) |
C5—C4—H4 | 120.7 | C23—C22—H22 | 120.3 |
C6—C5—C4 | 121.2 (5) | C21—C22—H22 | 120.3 |
C6—C5—H5 | 119.4 | C24—C23—C22 | 120.8 (4) |
C4—C5—H5 | 119.4 | C24—C23—O3 | 115.3 (5) |
C5—C6—C1 | 119.3 (5) | C22—C23—O3 | 123.9 (4) |
C5—C6—H6 | 120.4 | C23—C24—C25 | 120.3 (4) |
C1—C6—H6 | 120.4 | C23—C24—H24 | 119.9 |
N2—C7—C8 | 111.8 (3) | C25—C24—H24 | 119.9 |
N2—C7—S1 | 121.9 (3) | C20—C25—C24 | 118.7 (4) |
C8—C7—S1 | 126.3 (3) | C20—C25—H25 | 120.7 |
C9—C8—C7 | 104.9 (3) | C24—C25—H25 | 120.7 |
C9—C8—C11 | 119.9 (3) | O3—C26—C27 | 105.7 (5) |
C7—C8—C11 | 135.1 (3) | O3—C26—H26A | 110.6 |
N1—C9—C8 | 108.0 (3) | C27—C26—H26A | 110.6 |
N1—C9—N4 | 125.2 (3) | O3—C26—H26B | 110.6 |
C8—C9—N4 | 126.8 (4) | C27—C26—H26B | 110.6 |
S1—C10—H10A | 109.5 | H26A—C26—H26B | 108.7 |
S1—C10—H10B | 109.5 | O5—C27—O4 | 128.6 (11) |
H10A—C10—H10B | 109.5 | O5—C27—C26 | 109.3 (9) |
S1—C10—H10C | 109.5 | O4—C27—C26 | 120.9 (10) |
H10A—C10—H10C | 109.5 | O5—C28—C29 | 113.4 (10) |
H10B—C10—H10C | 109.5 | O5—C28—H28A | 108.9 |
O1—C11—C8 | 128.5 (4) | C29—C28—H28A | 108.9 |
O1—C11—N3 | 119.9 (3) | O5—C28—H28B | 108.9 |
C8—C11—N3 | 111.6 (3) | C29—C28—H28B | 108.9 |
N4—C12—O2 | 120.7 (3) | H28A—C28—H28B | 107.7 |
N4—C12—N3 | 127.4 (3) | C28—C29—H29A | 109.5 |
O2—C12—N3 | 111.9 (3) | C28—C29—H29B | 109.5 |
C14—C13—C18 | 120.1 (4) | H29A—C29—H29B | 109.5 |
C14—C13—N3 | 119.4 (4) | C28—C29—H29C | 109.5 |
C18—C13—N3 | 120.5 (4) | H29A—C29—H29C | 109.5 |
C13—C14—C15 | 119.6 (5) | H29B—C29—H29C | 109.5 |
C13—C14—H14 | 120.2 | C9—N1—N2 | 110.2 (3) |
C15—C14—H14 | 120.2 | C9—N1—C1 | 131.7 (3) |
C16—C15—C14 | 120.3 (5) | N2—N1—C1 | 118.1 (3) |
C16—C15—C19 | 121.3 (6) | C7—N2—N1 | 105.1 (3) |
C14—C15—C19 | 118.4 (6) | C12—N3—C13 | 120.4 (3) |
C17—C16—C15 | 120.1 (5) | C12—N3—C11 | 121.6 (3) |
C17—C16—H16 | 119.9 | C13—N3—C11 | 117.9 (3) |
C15—C16—H16 | 119.9 | C12—N4—C9 | 112.6 (3) |
C16—C17—C18 | 120.4 (6) | C12—O2—C20 | 116.6 (3) |
C16—C17—H17 | 119.8 | C26—O3—C23 | 119.1 (5) |
C18—C17—H17 | 119.8 | C27—O5—C28 | 115.9 (10) |
C13—C18—C17 | 119.5 (5) | C7—S1—C10 | 100.4 (2) |
C13—C18—H18 | 120.2 | | |
| | | |
C6—C1—C2—C3 | 2.9 (7) | O3—C26—C27—O4 | 29.7 (11) |
N1—C1—C2—C3 | −178.6 (4) | C8—C9—N1—N2 | 0.9 (4) |
C1—C2—C3—C4 | −0.7 (8) | N4—C9—N1—N2 | −179.7 (3) |
C2—C3—C4—C5 | −1.5 (9) | C8—C9—N1—C1 | 179.5 (3) |
C3—C4—C5—C6 | 1.4 (9) | N4—C9—N1—C1 | −1.1 (6) |
C4—C5—C6—C1 | 0.9 (8) | C2—C1—N1—C9 | −168.6 (4) |
C2—C1—C6—C5 | −3.0 (7) | C6—C1—N1—C9 | 9.9 (6) |
N1—C1—C6—C5 | 178.6 (4) | C2—C1—N1—N2 | 10.0 (5) |
N2—C7—C8—C9 | 1.3 (4) | C6—C1—N1—N2 | −171.6 (4) |
S1—C7—C8—C9 | −178.8 (3) | C8—C7—N2—N1 | −0.8 (4) |
N2—C7—C8—C11 | 177.6 (4) | S1—C7—N2—N1 | 179.3 (3) |
S1—C7—C8—C11 | −2.5 (7) | C9—N1—N2—C7 | 0.0 (4) |
C7—C8—C9—N1 | −1.3 (4) | C1—N1—N2—C7 | −178.9 (3) |
C11—C8—C9—N1 | −178.3 (3) | N4—C12—N3—C13 | −178.8 (4) |
C7—C8—C9—N4 | 179.3 (4) | O2—C12—N3—C13 | 1.5 (5) |
C11—C8—C9—N4 | 2.3 (6) | N4—C12—N3—C11 | −0.9 (7) |
C9—C8—C11—O1 | 176.5 (4) | O2—C12—N3—C11 | 179.4 (4) |
C7—C8—C11—O1 | 0.6 (8) | C14—C13—N3—C12 | 79.1 (5) |
C9—C8—C11—N3 | −1.4 (5) | C18—C13—N3—C12 | −99.8 (5) |
C7—C8—C11—N3 | −177.3 (4) | C14—C13—N3—C11 | −98.9 (5) |
C18—C13—C14—C15 | −0.8 (7) | C18—C13—N3—C11 | 82.2 (5) |
N3—C13—C14—C15 | −179.7 (4) | O1—C11—N3—C12 | −177.4 (4) |
C13—C14—C15—C16 | −0.6 (8) | C8—C11—N3—C12 | 0.8 (5) |
C13—C14—C15—C19 | 177.8 (5) | O1—C11—N3—C13 | 0.6 (6) |
C14—C15—C16—C17 | 2.2 (9) | C8—C11—N3—C13 | 178.7 (3) |
C19—C15—C16—C17 | −176.1 (7) | O2—C12—N4—C9 | −178.9 (4) |
C15—C16—C17—C18 | −2.3 (9) | N3—C12—N4—C9 | 1.4 (6) |
C14—C13—C18—C17 | 0.7 (8) | N1—C9—N4—C12 | 178.5 (4) |
N3—C13—C18—C17 | 179.5 (4) | C8—C9—N4—C12 | −2.1 (6) |
C16—C17—C18—C13 | 0.9 (9) | N4—C12—O2—C20 | 5.2 (6) |
C25—C20—C21—C22 | −2.0 (7) | N3—C12—O2—C20 | −175.1 (4) |
O2—C20—C21—C22 | −177.8 (4) | C21—C20—O2—C12 | −111.3 (5) |
C20—C21—C22—C23 | 0.8 (7) | C25—C20—O2—C12 | 72.9 (5) |
C21—C22—C23—C24 | 0.0 (8) | C27—C26—O3—C23 | 69.9 (7) |
C21—C22—C23—O3 | 179.4 (4) | C24—C23—O3—C26 | −164.6 (5) |
C22—C23—C24—C25 | 0.4 (8) | C22—C23—O3—C26 | 16.0 (7) |
O3—C23—C24—C25 | −179.0 (5) | O4—C27—O5—C28 | −13.5 (18) |
C21—C20—C25—C24 | 2.4 (7) | C26—C27—O5—C28 | 178.9 (8) |
O2—C20—C25—C24 | 178.0 (4) | C29—C28—O5—C27 | −69.2 (14) |
C23—C24—C25—C20 | −1.6 (8) | N2—C7—S1—C10 | −1.6 (4) |
O3—C26—C27—O5 | −161.5 (8) | C8—C7—S1—C10 | 178.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O1i | 0.93 | 2.45 | 3.275 (6) | 148 |
C25—H25···O1ii | 0.93 | 2.49 | 3.141 (5) | 127 |
C6—H6···N4 | 0.93 | 2.32 | 2.969 (6) | 126 |
Symmetry codes: (i) −y+1, x−1, z+1/4; (ii) y, −x+1, z−1/4. |
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