Ethyl {4-[5-(3-methyl­phen­yl)-3-methyl­sulfanyl-4-oxo-1-phenyl­pyrazolo[3,4-d]pyrimidin-6-yl­oxy]phen­oxy}acetate

The title compound, C₂₉H₂₆N₄O₅S, 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.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.30 × 0.20 × 0.04 mm
F(000) = 1136

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.12P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1^i	0.93	2.45	3.275 (6)	148
C25—H25···O1^ii	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.