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

In the title compound, C₂₇H₂₅N₅O₈, the o-vanillin (2-hydr­oxy-3-methoxy­benzaldehyde) group makes dihedral angles of 10.42 (9), 33.90 (9) and 61.62 (8)° with the pyrazolone ring, the terminal dinitro­benzene ring and the terminal phenyl ring, respectively. The crystal packing is stabilized by an inter­molecular C—H...O=C hydrogen bond that forms a centrosymmetric dimer, together with an inter­molecular C—H...O=N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C1      ..       6.32 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C18     ..       5.13 su

   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
   2 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
   0 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, 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-{2-[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 = 1.404 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.307 (7) Å	Cell parameters from 1737 reflections
b = 12.13 (1) Å	θ = 2.3–24.2°
c = 12.718 (10) Å	µ = 0.11 mm^−1
α = 67.920 (13)°	T = 294 K
β = 89.065 (13)°	Block, yellow
γ = 77.497 (12)°	0.24 × 0.20 × 0.16 mm
V = 1295.6 (18) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4537 independent reflections
Radiation source: fine-focus sealed tube	2634 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.958, Tmax = 0.983	k = −14→14
6619 measured reflections	l = −15→9

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0418P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4537 reflections	Δρmax = 0.17 e Å^−3
365 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0196 (16)

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	0.5960 (2)	−0.36950 (18)	0.88966 (17)	0.0844 (7)
O2	0.5262 (2)	−0.24335 (19)	0.97340 (17)	0.0901 (7)
O3	0.18376 (19)	0.13644 (17)	0.77325 (17)	0.0699 (6)
O4	0.0484 (2)	0.14903 (19)	0.63122 (17)	0.0817 (7)
O5	0.19790 (17)	0.06103 (14)	0.49367 (13)	0.0511 (5)
O6	0.15683 (16)	0.24641 (14)	0.27387 (12)	0.0451 (4)
O7	−0.05455 (18)	0.31832 (15)	0.10204 (13)	0.0572 (5)
O8	0.41731 (17)	0.20054 (15)	0.58410 (13)	0.0498 (5)
N1	0.5293 (2)	−0.2715 (2)	0.89018 (19)	0.0593 (6)
N2	0.1572 (2)	0.1023 (2)	0.69760 (19)	0.0527 (6)
N3	0.21490 (19)	0.46098 (17)	0.44141 (15)	0.0392 (5)
N4	0.4485 (2)	0.43169 (18)	0.67365 (15)	0.0421 (5)
N5	0.4808 (2)	0.31009 (18)	0.68486 (16)	0.0437 (5)
C1	0.2624 (2)	−0.0035 (2)	0.6903 (2)	0.0398 (6)
C2	0.3434 (3)	−0.0840 (2)	0.7893 (2)	0.0442 (6)
H2	0.3286	−0.0724	0.8573	0.053*
C3	0.4465 (3)	−0.1817 (2)	0.7850 (2)	0.0449 (6)
C4	0.4736 (3)	−0.1978 (2)	0.6838 (2)	0.0465 (6)
H4	0.5462	−0.2632	0.6824	0.056*
C5	0.3927 (3)	−0.1165 (2)	0.5855 (2)	0.0438 (6)
H5	0.4117	−0.1266	0.5173	0.053*
C6	0.2823 (2)	−0.0191 (2)	0.58679 (19)	0.0399 (6)
C7	0.2059 (3)	0.0369 (2)	0.39068 (19)	0.0521 (7)
H7A	0.1807	−0.0405	0.4038	0.063*
H7B	0.3047	0.0336	0.3647	0.063*
C8	0.0974 (3)	0.1397 (2)	0.3042 (2)	0.0555 (7)
H8A	0.0837	0.1211	0.2377	0.067*
H8B	0.0027	0.1528	0.3359	0.067*
C9	0.0580 (2)	0.3580 (2)	0.24405 (18)	0.0386 (6)
C10	−0.0492 (2)	0.3993 (2)	0.15299 (19)	0.0423 (6)
C11	−0.1388 (3)	0.5151 (2)	0.1201 (2)	0.0491 (7)
H11	−0.2097	0.5434	0.0596	0.059*
C12	−0.1224 (3)	0.5889 (2)	0.1778 (2)	0.0508 (7)
H12	−0.1827	0.6670	0.1555	0.061*
C13	−0.0188 (2)	0.5488 (2)	0.26726 (19)	0.0462 (6)
H13	−0.0101	0.5996	0.3051	0.055*
C14	0.0738 (2)	0.4324 (2)	0.30229 (18)	0.0375 (6)
C15	−0.1691 (3)	0.3530 (3)	0.0141 (2)	0.0637 (8)
H15A	−0.2631	0.3741	0.0423	0.095*
H15B	−0.1673	0.2860	−0.0091	0.095*
H15C	−0.1536	0.4222	−0.0499	0.095*
C16	0.1813 (2)	0.3867 (2)	0.40096 (18)	0.0395 (6)
H16	0.2252	0.3037	0.4342	0.047*
C17	0.3141 (2)	0.4183 (2)	0.53702 (18)	0.0366 (6)
C18	0.4018 (2)	0.2986 (2)	0.59851 (19)	0.0400 (6)
C19	0.3442 (2)	0.4949 (2)	0.58669 (19)	0.0397 (6)
C20	0.2751 (3)	0.6259 (2)	0.5573 (2)	0.0548 (7)
H20A	0.2283	0.6363	0.6219	0.082*
H20B	0.2027	0.6535	0.4946	0.082*
H20C	0.3494	0.6726	0.5365	0.082*
C21	0.4920 (3)	0.4677 (2)	0.7630 (2)	0.0548 (7)
H21A	0.4279	0.5438	0.7567	0.082*
H21B	0.5918	0.4772	0.7555	0.082*
H21C	0.4849	0.4060	0.8359	0.082*
C22	0.5946 (2)	0.2192 (2)	0.76237 (19)	0.0415 (6)
C23	0.7349 (3)	0.2380 (3)	0.7683 (2)	0.0526 (7)
H23	0.7574	0.3109	0.7210	0.063*
C24	0.8412 (3)	0.1471 (3)	0.8452 (2)	0.0671 (9)
H24	0.9349	0.1598	0.8521	0.081*
C25	0.8090 (3)	0.0376 (3)	0.9119 (3)	0.0736 (9)
H25	0.8819	−0.0241	0.9624	0.088*
C26	0.6697 (3)	0.0187 (3)	0.9043 (2)	0.0726 (9)
H26	0.6485	−0.0556	0.9494	0.087*
C27	0.5619 (3)	0.1099 (2)	0.8298 (2)	0.0569 (7)
H27	0.4673	0.0978	0.8250	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1026 (16)	0.0466 (14)	0.0828 (15)	0.0069 (12)	−0.0386 (12)	−0.0123 (11)
O2	0.1372 (19)	0.0744 (15)	0.0484 (13)	−0.0149 (14)	−0.0262 (13)	−0.0156 (12)
O3	0.0636 (12)	0.0804 (15)	0.0891 (15)	−0.0152 (11)	0.0111 (11)	−0.0592 (13)
O4	0.0618 (13)	0.0964 (17)	0.0712 (14)	0.0232 (12)	−0.0104 (11)	−0.0364 (13)
O5	0.0653 (11)	0.0394 (11)	0.0425 (10)	0.0019 (9)	−0.0138 (9)	−0.0158 (8)
O6	0.0505 (10)	0.0354 (10)	0.0477 (10)	−0.0067 (9)	−0.0106 (8)	−0.0150 (8)
O7	0.0702 (12)	0.0556 (12)	0.0459 (11)	−0.0071 (10)	−0.0219 (9)	−0.0221 (9)
O8	0.0586 (11)	0.0439 (11)	0.0536 (11)	−0.0094 (9)	−0.0075 (8)	−0.0266 (9)
N1	0.0698 (16)	0.0456 (16)	0.0553 (16)	−0.0181 (13)	−0.0161 (13)	−0.0076 (13)
N2	0.0474 (14)	0.0564 (15)	0.0555 (15)	−0.0094 (12)	0.0092 (12)	−0.0242 (13)
N3	0.0430 (11)	0.0427 (13)	0.0354 (11)	−0.0130 (10)	0.0001 (9)	−0.0169 (10)
N4	0.0507 (12)	0.0449 (13)	0.0387 (12)	−0.0163 (10)	−0.0021 (10)	−0.0215 (10)
N5	0.0496 (12)	0.0398 (13)	0.0451 (12)	−0.0085 (10)	−0.0102 (10)	−0.0205 (10)
C1	0.0394 (14)	0.0346 (15)	0.0462 (15)	−0.0065 (12)	0.0017 (12)	−0.0173 (12)
C2	0.0527 (15)	0.0436 (16)	0.0397 (15)	−0.0177 (14)	0.0024 (12)	−0.0159 (13)
C3	0.0516 (16)	0.0369 (16)	0.0412 (15)	−0.0130 (13)	−0.0110 (12)	−0.0069 (12)
C4	0.0480 (15)	0.0320 (15)	0.0550 (17)	−0.0024 (12)	−0.0074 (13)	−0.0147 (13)
C5	0.0574 (16)	0.0326 (15)	0.0416 (15)	−0.0065 (13)	−0.0026 (12)	−0.0160 (12)
C6	0.0457 (14)	0.0282 (14)	0.0429 (15)	−0.0073 (12)	−0.0060 (12)	−0.0107 (12)
C7	0.0752 (18)	0.0395 (16)	0.0438 (15)	−0.0106 (14)	−0.0135 (14)	−0.0187 (13)
C8	0.0712 (18)	0.0400 (17)	0.0541 (17)	−0.0109 (15)	−0.0227 (14)	−0.0165 (13)
C9	0.0395 (14)	0.0364 (15)	0.0357 (14)	−0.0080 (12)	−0.0020 (11)	−0.0091 (12)
C10	0.0460 (15)	0.0452 (16)	0.0355 (14)	−0.0104 (13)	−0.0045 (12)	−0.0149 (12)
C11	0.0472 (15)	0.0489 (18)	0.0433 (15)	−0.0059 (14)	−0.0121 (12)	−0.0111 (13)
C12	0.0501 (16)	0.0421 (17)	0.0536 (16)	−0.0016 (13)	−0.0076 (13)	−0.0154 (14)
C13	0.0484 (15)	0.0452 (17)	0.0470 (15)	−0.0107 (13)	0.0007 (13)	−0.0197 (13)
C14	0.0391 (13)	0.0378 (15)	0.0337 (13)	−0.0097 (12)	−0.0036 (11)	−0.0109 (11)
C15	0.0666 (18)	0.078 (2)	0.0502 (17)	−0.0205 (16)	−0.0164 (14)	−0.0260 (16)
C16	0.0430 (14)	0.0397 (15)	0.0361 (14)	−0.0101 (12)	−0.0017 (11)	−0.0141 (12)
C17	0.0404 (14)	0.0391 (15)	0.0337 (13)	−0.0136 (12)	0.0013 (11)	−0.0152 (12)
C18	0.0425 (14)	0.0494 (17)	0.0375 (14)	−0.0173 (13)	0.0015 (11)	−0.0231 (13)
C19	0.0450 (14)	0.0425 (16)	0.0351 (14)	−0.0162 (13)	0.0041 (12)	−0.0151 (12)
C20	0.0743 (19)	0.0443 (17)	0.0486 (16)	−0.0170 (15)	−0.0006 (14)	−0.0185 (13)
C21	0.0742 (18)	0.0558 (18)	0.0448 (15)	−0.0199 (15)	−0.0045 (13)	−0.0277 (14)
C22	0.0424 (15)	0.0495 (17)	0.0365 (14)	−0.0109 (13)	−0.0028 (12)	−0.0203 (13)
C23	0.0447 (15)	0.071 (2)	0.0465 (16)	−0.0222 (15)	0.0042 (13)	−0.0221 (14)
C24	0.0407 (16)	0.099 (3)	0.0620 (19)	−0.0107 (18)	−0.0045 (15)	−0.0337 (19)
C25	0.064 (2)	0.077 (3)	0.068 (2)	0.0095 (19)	−0.0268 (17)	−0.0277 (19)
C26	0.081 (2)	0.054 (2)	0.071 (2)	−0.0150 (18)	−0.0246 (18)	−0.0087 (16)
C27	0.0531 (17)	0.0550 (19)	0.0590 (17)	−0.0193 (15)	−0.0107 (14)	−0.0132 (15)

Geometric parameters (Å, º)

O1—N1	1.219 (3)	C9—C14	1.396 (3)
O2—N1	1.226 (3)	C9—C10	1.404 (3)
O3—N2	1.229 (2)	C10—C11	1.381 (3)
O4—N2	1.216 (2)	C11—C12	1.386 (3)
O5—C6	1.341 (3)	C11—H11	0.9300
O5—C7	1.443 (3)	C12—C13	1.370 (3)
O6—C9	1.381 (3)	C12—H12	0.9300
O6—C8	1.435 (3)	C13—C14	1.396 (3)
O7—C10	1.375 (3)	C13—H13	0.9300
O7—C15	1.434 (3)	C14—C16	1.470 (3)
O8—C18	1.248 (3)	C15—H15A	0.9600
N1—C3	1.464 (3)	C15—H15B	0.9600
N2—C1	1.469 (3)	C15—H15C	0.9600
N3—C16	1.285 (3)	C16—H16	0.9300
N3—C17	1.399 (3)	C17—C19	1.379 (3)
N4—C19	1.352 (3)	C17—C18	1.429 (3)
N4—N5	1.392 (3)	C19—C20	1.482 (3)
N4—C21	1.453 (3)	C20—H20A	0.9600
N5—C18	1.397 (3)	C20—H20B	0.9600
N5—C22	1.422 (3)	C20—H20C	0.9600
C1—C2	1.376 (3)	C21—H21A	0.9600
C1—C6	1.402 (3)	C21—H21B	0.9600
C2—C3	1.372 (3)	C21—H21C	0.9600
C2—H2	0.9300	C22—C27	1.378 (3)
C3—C4	1.384 (3)	C22—C23	1.381 (3)
C4—C5	1.373 (3)	C23—C24	1.378 (4)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.393 (3)	C24—C25	1.374 (4)
C5—H5	0.9300	C24—H24	0.9300
C7—C8	1.498 (3)	C25—C26	1.376 (4)
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—C27	1.375 (3)
C8—H8A	0.9700	C26—H26	0.9300
C8—H8B	0.9700	C27—H27	0.9300
C6—O5—C7	119.07 (18)	C13—C12—H12	119.5
C9—O6—C8	117.48 (18)	C11—C12—H12	119.5
C10—O7—C15	117.49 (19)	C12—C13—C14	120.8 (2)
O1—N1—O2	124.2 (2)	C12—C13—H13	119.6
O1—N1—C3	118.0 (2)	C14—C13—H13	119.6
O2—N1—C3	117.8 (2)	C13—C14—C9	118.3 (2)
O4—N2—O3	123.9 (2)	C13—C14—C16	121.1 (2)
O4—N2—C1	118.9 (2)	C9—C14—C16	120.5 (2)
O3—N2—C1	117.1 (2)	O7—C15—H15A	109.5
C16—N3—C17	120.8 (2)	O7—C15—H15B	109.5
C19—N4—N5	107.78 (17)	H15A—C15—H15B	109.5
C19—N4—C21	128.3 (2)	O7—C15—H15C	109.5
N5—N4—C21	121.68 (18)	H15A—C15—H15C	109.5
N4—N5—C18	109.48 (18)	H15B—C15—H15C	109.5
N4—N5—C22	122.97 (17)	N3—C16—C14	120.2 (2)
C18—N5—C22	126.85 (19)	N3—C16—H16	119.9
C2—C1—C6	122.0 (2)	C14—C16—H16	119.9
C2—C1—N2	116.5 (2)	C19—C17—N3	121.8 (2)
C6—C1—N2	121.5 (2)	C19—C17—C18	108.1 (2)
C3—C2—C1	118.3 (2)	N3—C17—C18	130.05 (19)
C3—C2—H2	120.9	O8—C18—N5	122.9 (2)
C1—C2—H2	120.9	O8—C18—C17	132.2 (2)
C2—C3—C4	121.6 (2)	N5—C18—C17	104.93 (19)
C2—C3—N1	119.2 (2)	N4—C19—C17	109.6 (2)
C4—C3—N1	119.2 (2)	N4—C19—C20	122.1 (2)
C5—C4—C3	119.6 (2)	C17—C19—C20	128.3 (2)
C5—C4—H4	120.2	C19—C20—H20A	109.5
C3—C4—H4	120.2	C19—C20—H20B	109.5
C4—C5—C6	120.7 (2)	H20A—C20—H20B	109.5
C4—C5—H5	119.6	C19—C20—H20C	109.5
C6—C5—H5	119.6	H20A—C20—H20C	109.5
O5—C6—C5	123.0 (2)	H20B—C20—H20C	109.5
O5—C6—C1	119.2 (2)	N4—C21—H21A	109.5
C5—C6—C1	117.8 (2)	N4—C21—H21B	109.5
O5—C7—C8	106.41 (19)	H21A—C21—H21B	109.5
O5—C7—H7A	110.4	N4—C21—H21C	109.5
C8—C7—H7A	110.4	H21A—C21—H21C	109.5
O5—C7—H7B	110.4	H21B—C21—H21C	109.5
C8—C7—H7B	110.4	C27—C22—C23	120.7 (2)
H7A—C7—H7B	108.6	C27—C22—N5	117.9 (2)
O6—C8—C7	106.95 (19)	C23—C22—N5	121.4 (2)
O6—C8—H8A	110.3	C24—C23—C22	119.1 (3)
C7—C8—H8A	110.3	C24—C23—H23	120.5
O6—C8—H8B	110.3	C22—C23—H23	120.5
C7—C8—H8B	110.3	C25—C24—C23	120.3 (3)
H8A—C8—H8B	108.6	C25—C24—H24	119.9
O6—C9—C14	117.98 (19)	C23—C24—H24	119.9
O6—C9—C10	121.3 (2)	C24—C25—C26	120.4 (3)
C14—C9—C10	120.6 (2)	C24—C25—H25	119.8
O7—C10—C11	124.8 (2)	C26—C25—H25	119.8
O7—C10—C9	115.5 (2)	C27—C26—C25	119.8 (3)
C11—C10—C9	119.7 (2)	C27—C26—H26	120.1
C10—C11—C12	119.5 (2)	C25—C26—H26	120.1
C10—C11—H11	120.2	C26—C27—C22	119.8 (3)
C12—C11—H11	120.2	C26—C27—H27	120.1
C13—C12—C11	121.1 (2)	C22—C27—H27	120.1
C19—N4—N5—C18	3.8 (2)	C11—C12—C13—C14	0.4 (4)
C21—N4—N5—C18	168.1 (2)	C12—C13—C14—C9	−0.1 (3)
C19—N4—N5—C22	174.8 (2)	C12—C13—C14—C16	−177.6 (2)
C21—N4—N5—C22	−20.9 (3)	O6—C9—C14—C13	175.47 (19)
O4—N2—C1—C2	−152.7 (2)	C10—C9—C14—C13	−0.4 (3)
O3—N2—C1—C2	25.7 (3)	O6—C9—C14—C16	−7.0 (3)
O4—N2—C1—C6	29.4 (3)	C10—C9—C14—C16	177.1 (2)
O3—N2—C1—C6	−152.2 (2)	C17—N3—C16—C14	178.33 (19)
C6—C1—C2—C3	0.1 (3)	C13—C14—C16—N3	−15.2 (3)
N2—C1—C2—C3	−177.8 (2)	C9—C14—C16—N3	167.3 (2)
C1—C2—C3—C4	2.4 (4)	C16—N3—C17—C19	−175.5 (2)
C1—C2—C3—N1	−177.3 (2)	C16—N3—C17—C18	6.0 (4)
O1—N1—C3—C2	164.6 (2)	N4—N5—C18—O8	175.3 (2)
O2—N1—C3—C2	−15.0 (3)	C22—N5—C18—O8	4.7 (4)
O1—N1—C3—C4	−15.1 (4)	N4—N5—C18—C17	−2.6 (2)
O2—N1—C3—C4	165.3 (2)	C22—N5—C18—C17	−173.2 (2)
C2—C3—C4—C5	−2.1 (4)	C19—C17—C18—O8	−177.0 (3)
N1—C3—C4—C5	177.6 (2)	N3—C17—C18—O8	1.6 (4)
C3—C4—C5—C6	−0.9 (4)	C19—C17—C18—N5	0.6 (2)
C7—O5—C6—C5	9.1 (3)	N3—C17—C18—N5	179.3 (2)
C7—O5—C6—C1	−172.5 (2)	N5—N4—C19—C17	−3.4 (3)
C4—C5—C6—O5	−178.4 (2)	C21—N4—C19—C17	−166.3 (2)
C4—C5—C6—C1	3.2 (3)	N5—N4—C19—C20	174.9 (2)
C2—C1—C6—O5	178.6 (2)	C21—N4—C19—C20	11.9 (4)
N2—C1—C6—O5	−3.6 (3)	N3—C17—C19—N4	−177.08 (19)
C2—C1—C6—C5	−2.9 (3)	C18—C17—C19—N4	1.7 (3)
N2—C1—C6—C5	174.9 (2)	N3—C17—C19—C20	4.8 (4)
C6—O5—C7—C8	178.5 (2)	C18—C17—C19—C20	−176.4 (2)
C9—O6—C8—C7	−148.47 (19)	N4—N5—C22—C27	132.8 (2)
O5—C7—C8—O6	70.8 (2)	C18—N5—C22—C27	−57.8 (3)
C8—O6—C9—C14	125.7 (2)	N4—N5—C22—C23	−48.9 (3)
C8—O6—C9—C10	−58.5 (3)	C18—N5—C22—C23	120.5 (3)
C15—O7—C10—C11	−5.1 (3)	C27—C22—C23—C24	−2.0 (4)
C15—O7—C10—C9	175.6 (2)	N5—C22—C23—C24	179.8 (2)
O6—C9—C10—O7	4.3 (3)	C22—C23—C24—C25	2.5 (4)
C14—C9—C10—O7	180.0 (2)	C23—C24—C25—C26	−1.5 (4)
O6—C9—C10—C11	−175.1 (2)	C24—C25—C26—C27	−0.2 (4)
C14—C9—C10—C11	0.6 (3)	C25—C26—C27—C22	0.7 (4)
O7—C10—C11—C12	−179.6 (2)	C23—C22—C27—C26	0.4 (4)
C9—C10—C11—C12	−0.4 (4)	N5—C22—C27—C26	178.7 (2)
C10—C11—C12—C13	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21C···O2^i	0.96	2.50	3.463 (4)	179
C5—H5···O8^ii	0.93	2.28	3.093 (3)	146

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