(E)-4-{4-[2-(2,4-Dinitro­phen­oxy)eth­oxy]-3-methoxy­benzyl­ideneamino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

In the title compound, C₂₇H₂₅N₅O₈, the p-vanillin (4-hydr­oxy-3-methoxy­benzaldehyde) group makes dihedral angles of 5.80 (8), 66.34 (6) and 68.13 (7)° with the pyrazolone ring, the terminal dinitro­benzene ring and the terminal phenyl ring, respectively. The crystal packing is stabilized by inter­molecular C—H...O=C and C—H...O=N hydrogen bonds that form centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.131
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C16     ..       5.06 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT430_ALERT_2_C Short Inter D...A Contact  O8     ..  N1      ..       2.88 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-4-{4-[2-(2,4-Dinitrophenoxy)ethoxy]-3-methoxybenzylideneamino}-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C27H25N5O8	Z = 2
Mr = 547.52	F(000) = 572
Triclinic, P1	Dx = 1.406 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.032 (4) Å	Cell parameters from 1884 reflections
b = 12.288 (5) Å	θ = 2.3–24.0°
c = 13.054 (5) Å	µ = 0.11 mm^−1
α = 63.883 (7)°	T = 294 K
β = 83.801 (7)°	Block, yellow
γ = 88.328 (7)°	0.26 × 0.20 × 0.14 mm
V = 1293.0 (9) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5269 independent reflections
Radiation source: fine-focus sealed tube	2900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.959, Tmax = 0.985	k = −15→8
7445 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0611P)^2] where P = (Fo^2 + 2Fc^2)/3
5269 reflections	(Δ/σ)max = 0.004
364 parameters	Δρmax = 0.21 e Å^−3
6 restraints	Δρmin = −0.20 e Å^−3

Special details

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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1966 (2)	−0.11884 (17)	0.60606 (15)	0.0730 (6)
O2	0.0386 (2)	0.01617 (17)	0.60561 (15)	0.0699 (5)
O3	0.2103 (3)	0.43787 (19)	0.38763 (18)	0.1026 (8)
O4	0.2569 (2)	0.48046 (15)	0.21038 (15)	0.0638 (5)
O5	0.49496 (16)	0.34614 (12)	0.20082 (12)	0.0472 (4)
O6	0.76461 (17)	0.49172 (13)	0.12811 (12)	0.0489 (4)
O7	0.8650 (2)	0.59202 (15)	0.24322 (13)	0.0652 (5)
O8	1.32700 (18)	1.07466 (15)	−0.31314 (14)	0.0605 (5)
N1	0.1525 (2)	−0.0153 (2)	0.56690 (17)	0.0552 (6)
N2	0.2503 (2)	0.40974 (18)	0.31061 (19)	0.0514 (5)
N3	1.2000 (2)	0.95340 (16)	−0.05281 (16)	0.0453 (5)
N4	1.4461 (2)	1.19720 (16)	−0.25385 (16)	0.0479 (5)
N5	1.4664 (2)	1.19471 (16)	−0.14820 (16)	0.0462 (5)
C1	0.4463 (2)	0.13228 (19)	0.32334 (19)	0.0450 (6)
H1	0.5274	0.1099	0.2870	0.054*
C2	0.3598 (3)	0.0445 (2)	0.41343 (19)	0.0475 (6)
H2	0.3815	−0.0369	0.4372	0.057*
C3	0.2413 (3)	0.0774 (2)	0.46814 (19)	0.0459 (6)
C4	0.2058 (2)	0.1963 (2)	0.43438 (19)	0.0473 (6)
H4	0.1259	0.2177	0.4726	0.057*
C5	0.2905 (2)	0.28330 (19)	0.34301 (18)	0.0413 (5)
C6	0.4133 (2)	0.25454 (19)	0.28611 (18)	0.0390 (5)
C7	0.6335 (2)	0.31692 (19)	0.15436 (19)	0.0445 (6)
H7A	0.6152	0.2648	0.1186	0.053*
H7B	0.6965	0.2744	0.2151	0.053*
C8	0.7089 (2)	0.43251 (19)	0.06731 (18)	0.0423 (5)
H8A	0.7899	0.4154	0.0217	0.051*
H8B	0.6386	0.4837	0.0164	0.051*
C9	0.8513 (2)	0.59369 (18)	0.06529 (18)	0.0408 (5)
C10	0.8834 (2)	0.64507 (19)	−0.05188 (19)	0.0444 (6)
H10	0.8449	0.6104	−0.0942	0.053*
C11	0.9734 (2)	0.74887 (19)	−0.1073 (2)	0.0463 (6)
H11	0.9939	0.7837	−0.1867	0.056*
C12	1.0325 (2)	0.80076 (19)	−0.04542 (19)	0.0428 (6)
C13	0.9982 (2)	0.7489 (2)	0.0733 (2)	0.0471 (6)
H13	1.0373	0.7835	0.1155	0.057*
C14	0.9076 (3)	0.6476 (2)	0.12879 (19)	0.0445 (6)
C15	0.9226 (3)	0.6404 (2)	0.3123 (2)	0.0659 (8)
H15A	1.0294	0.6386	0.3037	0.099*
H15B	0.8860	0.5925	0.3912	0.099*
H15C	0.8912	0.7225	0.2884	0.099*
C16	1.1299 (2)	0.9080 (2)	−0.1056 (2)	0.0484 (6)
H16	1.1415	0.9447	−0.1854	0.058*
C17	1.2959 (2)	1.05284 (18)	−0.11653 (19)	0.0413 (5)
C18	1.3674 (2)	1.11252 (19)	−0.0679 (2)	0.0424 (5)
C19	1.3479 (3)	1.0968 (2)	0.0518 (2)	0.0550 (6)
H19A	1.4426	1.0815	0.0821	0.082*
H19B	1.2810	1.0295	0.0974	0.082*
H19C	1.3074	1.1691	0.0535	0.082*
C20	1.3488 (2)	1.10364 (19)	−0.2364 (2)	0.0446 (6)
C21	1.5177 (3)	1.3055 (2)	−0.1483 (2)	0.0680 (8)
H21A	1.4427	1.3658	−0.1737	0.102*
H21B	1.6078	1.3342	−0.1992	0.102*
H21C	1.5365	1.2897	−0.0721	0.102*
C22	1.5591 (3)	1.2469 (2)	−0.3487 (2)	0.0486 (6)
C23	1.7049 (3)	1.2150 (2)	−0.3350 (2)	0.0627 (7)
H23	1.7323	1.1636	−0.2628	0.075*
C24	1.8104 (3)	1.2594 (3)	−0.4288 (3)	0.0781 (9)
H24	1.9095	1.2380	−0.4200	0.094*
C25	1.7700 (4)	1.3349 (3)	−0.5348 (3)	0.0816 (10)
H25	1.8415	1.3646	−0.5980	0.098*
C26	1.6259 (4)	1.3663 (3)	−0.5478 (3)	0.0904 (11)
H26	1.5988	1.4179	−0.6200	0.108*
C27	1.5185 (3)	1.3219 (2)	−0.4539 (2)	0.0734 (8)
H27	1.4195	1.3433	−0.4629	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0952 (15)	0.0452 (11)	0.0564 (12)	−0.0177 (10)	−0.0053 (10)	−0.0016 (9)
O2	0.0498 (12)	0.0828 (13)	0.0529 (12)	−0.0207 (10)	0.0057 (9)	−0.0091 (10)
O3	0.160 (2)	0.0827 (15)	0.0659 (14)	0.0436 (15)	−0.0041 (14)	−0.0382 (12)
O4	0.0825 (14)	0.0445 (10)	0.0505 (12)	−0.0030 (9)	−0.0065 (10)	−0.0082 (9)
O5	0.0395 (9)	0.0410 (9)	0.0490 (10)	−0.0097 (7)	0.0074 (7)	−0.0109 (7)
O6	0.0554 (10)	0.0465 (9)	0.0394 (9)	−0.0228 (8)	0.0064 (8)	−0.0150 (7)
O7	0.0857 (13)	0.0692 (12)	0.0375 (10)	−0.0345 (10)	0.0052 (9)	−0.0208 (9)
O8	0.0623 (12)	0.0700 (12)	0.0557 (11)	−0.0253 (9)	0.0051 (9)	−0.0345 (10)
N1	0.0505 (14)	0.0582 (15)	0.0421 (13)	−0.0220 (11)	−0.0065 (11)	−0.0070 (11)
N2	0.0532 (13)	0.0481 (13)	0.0495 (14)	0.0012 (10)	−0.0034 (10)	−0.0187 (11)
N3	0.0387 (11)	0.0400 (11)	0.0536 (12)	−0.0077 (9)	0.0039 (9)	−0.0189 (9)
N4	0.0493 (12)	0.0499 (12)	0.0455 (12)	−0.0183 (9)	0.0039 (9)	−0.0227 (10)
N5	0.0497 (12)	0.0432 (11)	0.0480 (12)	−0.0139 (9)	0.0006 (10)	−0.0225 (9)
C1	0.0418 (13)	0.0411 (13)	0.0480 (14)	−0.0067 (10)	0.0007 (11)	−0.0167 (11)
C2	0.0500 (15)	0.0395 (13)	0.0489 (15)	−0.0093 (11)	−0.0087 (12)	−0.0145 (11)
C3	0.0423 (14)	0.0457 (14)	0.0388 (14)	−0.0144 (11)	−0.0062 (11)	−0.0071 (11)
C4	0.0400 (14)	0.0523 (15)	0.0411 (14)	−0.0061 (11)	−0.0003 (11)	−0.0132 (11)
C5	0.0402 (13)	0.0377 (13)	0.0407 (13)	−0.0026 (10)	−0.0047 (11)	−0.0121 (10)
C6	0.0351 (12)	0.0395 (13)	0.0360 (13)	−0.0112 (10)	−0.0007 (10)	−0.0107 (10)
C7	0.0405 (13)	0.0429 (13)	0.0466 (14)	−0.0084 (10)	0.0042 (11)	−0.0180 (11)
C8	0.0374 (13)	0.0432 (13)	0.0416 (13)	−0.0098 (10)	−0.0001 (10)	−0.0146 (11)
C9	0.0365 (13)	0.0367 (12)	0.0416 (14)	−0.0087 (10)	0.0001 (10)	−0.0108 (11)
C10	0.0441 (14)	0.0449 (13)	0.0418 (14)	−0.0104 (11)	0.0013 (11)	−0.0175 (11)
C11	0.0449 (14)	0.0433 (13)	0.0409 (14)	−0.0075 (11)	0.0053 (11)	−0.0112 (11)
C12	0.0367 (13)	0.0385 (13)	0.0474 (15)	−0.0056 (10)	0.0010 (11)	−0.0146 (11)
C13	0.0449 (14)	0.0468 (14)	0.0495 (15)	−0.0114 (11)	−0.0001 (11)	−0.0213 (11)
C14	0.0481 (14)	0.0467 (14)	0.0353 (13)	−0.0107 (11)	0.0031 (11)	−0.0157 (11)
C15	0.083 (2)	0.0697 (18)	0.0478 (16)	−0.0087 (15)	−0.0075 (15)	−0.0281 (14)
C16	0.0416 (14)	0.0433 (14)	0.0516 (15)	−0.0065 (11)	0.0050 (12)	−0.0147 (12)
C17	0.0376 (13)	0.0338 (12)	0.0499 (15)	−0.0035 (10)	0.0015 (11)	−0.0170 (11)
C18	0.0385 (13)	0.0375 (12)	0.0484 (14)	0.0007 (10)	−0.0020 (11)	−0.0169 (11)
C19	0.0617 (17)	0.0536 (15)	0.0504 (16)	0.0021 (12)	−0.0055 (13)	−0.0237 (12)
C20	0.0402 (14)	0.0429 (13)	0.0495 (15)	−0.0086 (10)	0.0016 (11)	−0.0200 (12)
C21	0.079 (2)	0.0593 (17)	0.0728 (19)	−0.0272 (14)	0.0067 (15)	−0.0373 (15)
C22	0.0498 (16)	0.0437 (14)	0.0480 (16)	−0.0182 (11)	0.0040 (12)	−0.0173 (12)
C23	0.0557 (18)	0.0626 (17)	0.0582 (18)	−0.0078 (14)	0.0034 (14)	−0.0175 (14)
C24	0.0596 (19)	0.089 (2)	0.085 (2)	−0.0206 (16)	0.0207 (17)	−0.043 (2)
C25	0.094 (3)	0.086 (2)	0.065 (2)	−0.046 (2)	0.0301 (19)	−0.0387 (19)
C26	0.107 (3)	0.092 (2)	0.0495 (19)	−0.036 (2)	0.0010 (19)	−0.0100 (16)
C27	0.0659 (19)	0.077 (2)	0.0583 (19)	−0.0131 (15)	−0.0079 (16)	−0.0114 (16)

Geometric parameters (Å, º)

O1—N1	1.217 (3)	C9—C10	1.374 (3)
O2—N1	1.225 (3)	C9—C14	1.407 (3)
O3—N2	1.217 (2)	C10—C11	1.390 (3)
O4—N2	1.207 (2)	C10—H10	0.9300
O5—C6	1.349 (2)	C11—C12	1.382 (3)
O5—C7	1.437 (3)	C11—H11	0.9300
O6—C9	1.367 (2)	C12—C13	1.394 (3)
O6—C8	1.424 (2)	C12—C16	1.461 (3)
O7—C14	1.356 (3)	C13—C14	1.372 (3)
O7—C15	1.424 (3)	C13—H13	0.9300
O8—C20	1.237 (3)	C15—H15A	0.9600
N1—C3	1.463 (3)	C15—H15B	0.9600
N2—C5	1.465 (3)	C15—H15C	0.9600
N3—C16	1.281 (3)	C16—H16	0.9300
N3—C17	1.396 (3)	C17—C18	1.373 (3)
N4—C20	1.390 (3)	C17—C20	1.436 (3)
N4—N5	1.398 (2)	C18—C19	1.478 (3)
N4—C22	1.431 (3)	C19—H19A	0.9600
N5—C18	1.355 (3)	C19—H19B	0.9600
N5—C21	1.450 (3)	C19—H19C	0.9600
C1—C2	1.375 (3)	C21—H21A	0.9600
C1—C6	1.395 (3)	C21—H21B	0.9600
C1—H1	0.9300	C21—H21C	0.9600
C2—C3	1.372 (3)	C22—C27	1.357 (3)
C2—H2	0.9300	C22—C23	1.371 (3)
C3—C4	1.366 (3)	C23—C24	1.377 (4)
C4—C5	1.371 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.367 (4)
C5—C6	1.391 (3)	C24—H24	0.9300
C7—C8	1.497 (3)	C25—C26	1.353 (4)
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—C27	1.389 (4)
C8—H8A	0.9700	C26—H26	0.9300
C8—H8B	0.9700	C27—H27	0.9300
C6—O5—C7	117.82 (17)	C11—C12—C16	119.4 (2)
C9—O6—C8	117.11 (17)	C13—C12—C16	121.5 (2)
C14—O7—C15	117.44 (19)	C14—C13—C12	120.9 (2)
O1—N1—O2	123.9 (2)	C14—C13—H13	119.6
O1—N1—C3	118.1 (2)	C12—C13—H13	119.6
O2—N1—C3	118.0 (2)	O7—C14—C13	125.4 (2)
O4—N2—O3	123.1 (2)	O7—C14—C9	115.02 (19)
O4—N2—C5	119.4 (2)	C13—C14—C9	119.6 (2)
O3—N2—C5	117.5 (2)	O7—C15—H15A	109.5
C16—N3—C17	119.1 (2)	O7—C15—H15B	109.5
C20—N4—N5	109.36 (17)	H15A—C15—H15B	109.5
C20—N4—C22	123.64 (18)	O7—C15—H15C	109.5
N5—N4—C22	120.76 (17)	H15A—C15—H15C	109.5
C18—N5—N4	107.47 (17)	H15B—C15—H15C	109.5
C18—N5—C21	126.10 (19)	N3—C16—C12	122.6 (2)
N4—N5—C21	117.75 (18)	N3—C16—H16	118.7
C2—C1—C6	120.5 (2)	C12—C16—H16	118.7
C2—C1—H1	119.8	C18—C17—N3	123.0 (2)
C6—C1—H1	119.8	C18—C17—C20	108.11 (19)
C3—C2—C1	119.8 (2)	N3—C17—C20	128.6 (2)
C3—C2—H2	120.1	N5—C18—C17	109.5 (2)
C1—C2—H2	120.1	N5—C18—C19	121.51 (19)
C4—C3—C2	121.4 (2)	C17—C18—C19	128.9 (2)
C4—C3—N1	118.6 (2)	C18—C19—H19A	109.5
C2—C3—N1	120.0 (2)	C18—C19—H19B	109.5
C3—C4—C5	118.6 (2)	H19A—C19—H19B	109.5
C3—C4—H4	120.7	C18—C19—H19C	109.5
C5—C4—H4	120.7	H19A—C19—H19C	109.5
C4—C5—C6	122.1 (2)	H19B—C19—H19C	109.5
C4—C5—N2	116.9 (2)	O8—C20—N4	122.8 (2)
C6—C5—N2	120.93 (19)	O8—C20—C17	132.3 (2)
O5—C6—C5	118.26 (19)	N4—C20—C17	104.86 (19)
O5—C6—C1	124.1 (2)	N5—C21—H21A	109.5
C5—C6—C1	117.59 (19)	N5—C21—H21B	109.5
O5—C7—C8	108.38 (18)	H21A—C21—H21B	109.5
O5—C7—H7A	110.0	N5—C21—H21C	109.5
C8—C7—H7A	110.0	H21A—C21—H21C	109.5
O5—C7—H7B	110.0	H21B—C21—H21C	109.5
C8—C7—H7B	110.0	C27—C22—C23	120.5 (2)
H7A—C7—H7B	108.4	C27—C22—N4	118.8 (2)
O6—C8—C7	107.43 (18)	C23—C22—N4	120.6 (2)
O6—C8—H8A	110.2	C22—C23—C24	119.5 (3)
C7—C8—H8A	110.2	C22—C23—H23	120.2
O6—C8—H8B	110.2	C24—C23—H23	120.2
C7—C8—H8B	110.2	C25—C24—C23	120.2 (3)
H8A—C8—H8B	108.5	C25—C24—H24	119.9
O6—C9—C10	124.78 (19)	C23—C24—H24	119.9
O6—C9—C14	115.41 (19)	C26—C25—C24	120.1 (3)
C10—C9—C14	119.81 (19)	C26—C25—H25	120.0
C9—C10—C11	120.1 (2)	C24—C25—H25	120.0
C9—C10—H10	120.0	C25—C26—C27	120.3 (3)
C11—C10—H10	120.0	C25—C26—H26	119.9
C12—C11—C10	120.6 (2)	C27—C26—H26	119.9
C12—C11—H11	119.7	C22—C27—C26	119.5 (3)
C10—C11—H11	119.7	C22—C27—H27	120.2
C11—C12—C13	119.1 (2)	C26—C27—H27	120.2
C20—N4—N5—C18	−8.5 (2)	C15—O7—C14—C9	178.0 (2)
C22—N4—N5—C18	−161.70 (19)	C12—C13—C14—O7	−178.4 (2)
C20—N4—N5—C21	−158.2 (2)	C12—C13—C14—C9	1.5 (4)
C22—N4—N5—C21	48.6 (3)	O6—C9—C14—O7	−1.4 (3)
C6—C1—C2—C3	−0.9 (3)	C10—C9—C14—O7	177.8 (2)
C1—C2—C3—C4	0.6 (3)	O6—C9—C14—C13	178.7 (2)
C1—C2—C3—N1	−177.58 (19)	C10—C9—C14—C13	−2.1 (3)
O1—N1—C3—C4	−170.2 (2)	C17—N3—C16—C12	177.2 (2)
O2—N1—C3—C4	9.4 (3)	C11—C12—C16—N3	−172.9 (2)
O1—N1—C3—C2	8.1 (3)	C13—C12—C16—N3	6.7 (3)
O2—N1—C3—C2	−172.3 (2)	C16—N3—C17—C18	175.3 (2)
C2—C3—C4—C5	0.7 (3)	C16—N3—C17—C20	−11.0 (3)
N1—C3—C4—C5	178.94 (19)	N4—N5—C18—C17	6.6 (2)
C3—C4—C5—C6	−1.8 (3)	C21—N5—C18—C17	153.1 (2)
C3—C4—C5—N2	−179.09 (19)	N4—N5—C18—C19	−173.3 (2)
O4—N2—C5—C4	−141.2 (2)	C21—N5—C18—C19	−26.8 (3)
O3—N2—C5—C4	38.3 (3)	N3—C17—C18—N5	172.45 (19)
O4—N2—C5—C6	41.5 (3)	C20—C17—C18—N5	−2.3 (3)
O3—N2—C5—C6	−139.0 (2)	N3—C17—C18—C19	−7.6 (4)
C7—O5—C6—C5	170.78 (18)	C20—C17—C18—C19	177.6 (2)
C7—O5—C6—C1	−7.4 (3)	N5—N4—C20—O8	−169.9 (2)
C4—C5—C6—O5	−176.68 (19)	C22—N4—C20—O8	−17.6 (4)
N2—C5—C6—O5	0.5 (3)	N5—N4—C20—C17	6.9 (2)
C4—C5—C6—C1	1.6 (3)	C22—N4—C20—C17	159.1 (2)
N2—C5—C6—C1	178.74 (19)	C18—C17—C20—O8	173.5 (3)
C2—C1—C6—O5	177.96 (19)	N3—C17—C20—O8	−0.9 (4)
C2—C1—C6—C5	−0.2 (3)	C18—C17—C20—N4	−2.9 (2)
C6—O5—C7—C8	−176.24 (17)	N3—C17—C20—N4	−177.3 (2)
C9—O6—C8—C7	173.46 (18)	C20—N4—C22—C27	75.2 (3)
O5—C7—C8—O6	73.4 (2)	N5—N4—C22—C27	−135.5 (2)
C8—O6—C9—C10	2.5 (3)	C20—N4—C22—C23	−101.7 (3)
C8—O6—C9—C14	−178.29 (19)	N5—N4—C22—C23	47.5 (3)
O6—C9—C10—C11	−179.8 (2)	C27—C22—C23—C24	0.0 (4)
C14—C9—C10—C11	1.1 (3)	N4—C22—C23—C24	176.8 (2)
C9—C10—C11—C12	0.6 (3)	C22—C23—C24—C25	0.0 (4)
C10—C11—C12—C13	−1.3 (3)	C23—C24—C25—C26	0.1 (5)
C10—C11—C12—C16	178.4 (2)	C24—C25—C26—C27	−0.2 (5)
C11—C12—C13—C14	0.2 (3)	C23—C22—C27—C26	−0.1 (4)
C16—C12—C13—C14	−179.4 (2)	N4—C22—C27—C26	−177.0 (2)
C15—O7—C14—C13	−2.1 (4)	C25—C26—C27—C22	0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O8^i	0.93	2.50	3.258 (3)	139
C21—H21B···O4^ii	0.96	2.56	3.131 (3)	119

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z.