2,2-Dimethyl-5-(2-naphthyl-amino-methyl-ene)-1,3-dioxane-4,6-dione.

There are two unique mol-ecules in the asymmetric unit of the title compound, C(17)H(15)NO(4), which are linked into chains via inter-molecular N-H⋯O and C-H⋯O inter-actions; the chains are linked via weak C-H⋯O inter-actions, forming a parallel sheet structure. The molecule is approximately planar, with dihedral angles of 19.91 (4) and 11.06 (4)° between the naphthyl ring and the amino-methyl-ene group, and between the amino-methyl-ene unit and the planar part of the dioxane ring, respectively. The dioxane ring adopts a half-boat conformation, with the C atom between the dioxane O atoms 0.595 (8) Å out of the plane through the remaining atoms. The mol-ecule has an intra-molecular N-H⋯O hydrogen bond which stabilizes the planar conformation.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ▶). For the synthesis of related anti­tumor precursors, see: Ruchelman et al. (2003 ▶). For the crystal structures of other 5-aryl­amino­methyl­ene-2,2-dimethyl-1,3-dioxane-4,6-dione deriv­atives, see: Li et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C17H15NO4

M = 297.30

Triclinic,

a = 10.6204 (17) Å

b = 11.8220 (19) Å

c = 12.0143 (19) Å

α = 78.237 (2)°

β = 86.786 (2)°

γ = 82.469 (2)°

V = 1463.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

9205 measured reflections

6490 independent reflections

4313 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.11

6490 reflections

410 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038458/bv2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038458/bv2127Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15NO4	Z = 4
Mr = 297.30	F(000) = 624
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6204 (17) Å	Cell parameters from 2937 reflections
b = 11.8220 (19) Å	θ = 2.5–27.5°
c = 12.0143 (19) Å	µ = 0.10 mm−1
α = 78.237 (2)°	T = 153 K
β = 86.786 (2)°	Block, colourless
γ = 82.469 (2)°	0.25 × 0.22 × 0.20 mm
V = 1463.4 (4) Å3

Bruker SMART CCD area-detector diffractometer	4313 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.6°, θmin = 2.5°
φ and ω scans	h = −10→13
9205 measured reflections	k = −15→14
6490 independent reflections	l = −15→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.2303P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
6490 reflections	Δρmax = 0.23 e Å−3
410 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (2)

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.

	x	y	z	Uiso*/Ueq
O1	0.09234 (11)	0.24925 (9)	0.63633 (8)	0.0467 (3)
O2	−0.06511 (10)	0.17438 (10)	0.55278 (9)	0.0477 (3)
O3	0.17092 (13)	0.40987 (10)	0.55022 (9)	0.0590 (4)
O4	−0.13735 (13)	0.25516 (13)	0.38302 (11)	0.0739 (4)
N1	0.13306 (14)	0.48532 (12)	0.31953 (12)	0.0455 (3)
H1	0.1759 (19)	0.4990 (18)	0.3788 (17)	0.078 (7)*
C1	0.01090 (19)	0.07785 (16)	0.73214 (15)	0.0578 (5)
H1A	−0.0588	0.1241	0.7658	0.087*
H1B	0.0839	0.0615	0.7819	0.087*
H1C	−0.0170	0.0044	0.7235	0.087*
C2	0.15032 (16)	0.07683 (15)	0.55656 (15)	0.0534 (4)
H2A	0.1202	0.0048	0.5463	0.080*
H2B	0.2271	0.0577	0.6016	0.080*
H2C	0.1698	0.1239	0.4820	0.080*
C3	0.04856 (15)	0.14458 (13)	0.61769 (13)	0.0406 (4)
C4	0.10548 (16)	0.33504 (13)	0.54327 (13)	0.0413 (4)
C5	0.03603 (15)	0.33192 (13)	0.44535 (13)	0.0413 (4)
C6	−0.06033 (16)	0.25392 (15)	0.45320 (14)	0.0474 (4)
C7	0.05448 (15)	0.40537 (14)	0.34294 (13)	0.0450 (4)
H7	0.0050	0.3977	0.2820	0.054*
C8	0.15665 (15)	0.54980 (13)	0.20834 (12)	0.0412 (4)
C9	0.19882 (15)	0.65634 (14)	0.19600 (13)	0.0425 (4)
H9	0.2116	0.6864	0.2615	0.051*
C10	0.22353 (14)	0.72218 (13)	0.08622 (13)	0.0407 (4)
C11	0.26546 (18)	0.83343 (16)	0.06954 (15)	0.0562 (5)
H11	0.2766	0.8665	0.1335	0.067*
C12	0.2901 (2)	0.89383 (17)	−0.03759 (17)	0.0669 (6)
H12	0.3186	0.9682	−0.0474	0.080*
C13	0.27356 (19)	0.84666 (17)	−0.13264 (16)	0.0635 (5)
H13	0.2916	0.8891	−0.2066	0.076*
C14	0.23192 (17)	0.74096 (17)	−0.12038 (14)	0.0543 (5)
H14	0.2207	0.7102	−0.1858	0.065*
C15	0.20497 (15)	0.67593 (14)	−0.01052 (13)	0.0428 (4)
C16	0.16170 (17)	0.56607 (15)	0.00616 (14)	0.0525 (4)
H16	0.1483	0.5345	−0.0582	0.063*
C17	0.13853 (17)	0.50381 (15)	0.11220 (14)	0.0518 (4)
H17	0.1102	0.4294	0.1212	0.062*
O5	0.42844 (11)	0.73498 (10)	0.35805 (9)	0.0496 (3)
O6	0.57288 (11)	0.81921 (10)	0.44864 (10)	0.0524 (3)
O7	0.33468 (12)	0.58478 (10)	0.44833 (10)	0.0573 (3)
O8	0.62505 (15)	0.75181 (14)	0.62628 (12)	0.0866 (5)
N2	0.37240 (13)	0.50869 (12)	0.68054 (11)	0.0445 (3)
H2	0.3243 (19)	0.4993 (18)	0.6238 (17)	0.078 (7)*
C18	0.5313 (2)	0.89190 (17)	0.25626 (15)	0.0648 (5)
H18A	0.5608	0.9662	0.2598	0.097*
H18B	0.4678	0.9046	0.1974	0.097*
H18C	0.6035	0.8375	0.2377	0.097*
C19	0.36396 (17)	0.92034 (15)	0.40890 (17)	0.0641 (5)
H19A	0.3331	0.8835	0.4843	0.096*
H19B	0.2951	0.9340	0.3550	0.096*
H19C	0.3927	0.9947	0.4131	0.096*
C20	0.47273 (15)	0.84181 (14)	0.36956 (13)	0.0427 (4)
C21	0.40282 (15)	0.65788 (13)	0.45482 (13)	0.0409 (4)
C22	0.46411 (15)	0.66640 (14)	0.55547 (13)	0.0423 (4)
C23	0.55744 (17)	0.74667 (16)	0.55030 (15)	0.0527 (4)
C24	0.44707 (16)	0.59171 (14)	0.65771 (14)	0.0469 (4)
H24	0.4948	0.6011	0.7191	0.056*
C25	0.36078 (15)	0.43352 (13)	0.78831 (12)	0.0401 (4)
C26	0.25699 (15)	0.37528 (13)	0.81217 (12)	0.0401 (4)
H26	0.1945	0.3850	0.7563	0.048*
C27	0.24066 (15)	0.30061 (13)	0.91865 (12)	0.0393 (4)
C28	0.13167 (17)	0.24240 (15)	0.94677 (15)	0.0519 (4)
H28	0.0682	0.2506	0.8920	0.062*
C29	0.11669 (19)	0.17443 (17)	1.05196 (16)	0.0656 (5)
H29	0.0429	0.1360	1.0698	0.079*
C30	0.2093 (2)	0.16097 (18)	1.13367 (16)	0.0681 (6)
H30	0.1974	0.1139	1.2067	0.082*
C31	0.31577 (19)	0.21456 (16)	1.10953 (15)	0.0599 (5)
H31	0.3782	0.2040	1.1656	0.072*
C32	0.33477 (15)	0.28624 (14)	1.00126 (13)	0.0443 (4)
C33	0.44196 (16)	0.34644 (16)	0.97260 (15)	0.0554 (5)
H33	0.5062	0.3371	1.0268	0.066*
C34	0.45594 (16)	0.41743 (16)	0.86962 (15)	0.0538 (5)
H34	0.5296	0.4562	0.8523	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0684 (8)	0.0379 (6)	0.0360 (6)	−0.0205 (5)	−0.0011 (5)	−0.0034 (5)
O2	0.0396 (6)	0.0470 (7)	0.0538 (7)	−0.0157 (5)	−0.0014 (5)	0.0026 (5)
O3	0.0873 (9)	0.0488 (7)	0.0466 (7)	−0.0372 (7)	−0.0040 (6)	−0.0040 (6)
O4	0.0644 (9)	0.0939 (11)	0.0631 (8)	−0.0350 (8)	−0.0208 (7)	0.0064 (8)
N1	0.0535 (9)	0.0405 (8)	0.0391 (8)	−0.0105 (6)	0.0003 (6)	0.0024 (6)
C1	0.0670 (12)	0.0452 (10)	0.0570 (11)	−0.0183 (9)	0.0054 (9)	0.0046 (8)
C2	0.0477 (10)	0.0421 (10)	0.0709 (12)	−0.0088 (8)	0.0029 (9)	−0.0115 (9)
C3	0.0421 (9)	0.0341 (8)	0.0457 (9)	−0.0134 (7)	−0.0018 (7)	−0.0024 (7)
C4	0.0536 (10)	0.0342 (8)	0.0362 (8)	−0.0135 (7)	0.0037 (7)	−0.0036 (6)
C5	0.0444 (9)	0.0373 (8)	0.0403 (8)	−0.0087 (7)	−0.0002 (7)	−0.0011 (7)
C6	0.0444 (9)	0.0512 (10)	0.0446 (9)	−0.0110 (8)	−0.0030 (7)	−0.0012 (8)
C7	0.0450 (9)	0.0456 (9)	0.0417 (9)	−0.0063 (7)	−0.0036 (7)	−0.0012 (7)
C8	0.0452 (9)	0.0379 (9)	0.0361 (8)	−0.0043 (7)	0.0025 (7)	0.0010 (7)
C9	0.0476 (9)	0.0441 (9)	0.0353 (8)	−0.0095 (7)	−0.0031 (7)	−0.0037 (7)
C10	0.0401 (9)	0.0402 (9)	0.0388 (8)	−0.0062 (7)	−0.0012 (6)	−0.0002 (7)
C11	0.0656 (12)	0.0491 (10)	0.0535 (10)	−0.0188 (9)	0.0028 (9)	−0.0034 (8)
C12	0.0770 (14)	0.0516 (11)	0.0663 (13)	−0.0209 (10)	0.0066 (11)	0.0077 (10)
C13	0.0665 (13)	0.0625 (12)	0.0494 (11)	−0.0103 (10)	0.0036 (9)	0.0175 (9)
C14	0.0540 (11)	0.0664 (12)	0.0374 (9)	−0.0041 (9)	0.0004 (8)	−0.0011 (8)
C15	0.0413 (9)	0.0462 (9)	0.0376 (8)	−0.0031 (7)	0.0001 (7)	−0.0022 (7)
C16	0.0683 (12)	0.0515 (10)	0.0402 (9)	−0.0112 (9)	0.0065 (8)	−0.0147 (8)
C17	0.0689 (12)	0.0381 (9)	0.0501 (10)	−0.0131 (8)	0.0101 (8)	−0.0118 (8)
O5	0.0693 (8)	0.0437 (7)	0.0390 (6)	−0.0249 (6)	0.0039 (5)	−0.0060 (5)
O6	0.0456 (7)	0.0548 (7)	0.0549 (7)	−0.0212 (6)	−0.0028 (5)	0.0036 (6)
O7	0.0753 (9)	0.0505 (7)	0.0513 (7)	−0.0328 (7)	−0.0010 (6)	−0.0066 (6)
O8	0.0945 (11)	0.1021 (12)	0.0665 (9)	−0.0550 (10)	−0.0292 (8)	0.0102 (8)
N2	0.0478 (8)	0.0442 (8)	0.0391 (8)	−0.0097 (6)	0.0028 (6)	−0.0011 (6)
C18	0.0769 (13)	0.0625 (12)	0.0536 (11)	−0.0314 (11)	0.0089 (10)	0.0032 (9)
C19	0.0556 (11)	0.0437 (10)	0.0898 (15)	−0.0043 (9)	0.0040 (10)	−0.0085 (10)
C20	0.0454 (9)	0.0363 (8)	0.0474 (9)	−0.0150 (7)	−0.0019 (7)	−0.0039 (7)
C21	0.0474 (9)	0.0360 (8)	0.0398 (8)	−0.0116 (7)	0.0072 (7)	−0.0068 (7)
C22	0.0436 (9)	0.0407 (9)	0.0415 (9)	−0.0106 (7)	0.0021 (7)	−0.0036 (7)
C23	0.0522 (10)	0.0569 (11)	0.0488 (10)	−0.0182 (9)	−0.0052 (8)	−0.0019 (8)
C24	0.0478 (10)	0.0474 (10)	0.0448 (9)	−0.0101 (8)	0.0012 (7)	−0.0052 (8)
C25	0.0424 (9)	0.0389 (8)	0.0361 (8)	−0.0035 (7)	0.0032 (7)	−0.0030 (7)
C26	0.0450 (9)	0.0404 (9)	0.0345 (8)	−0.0057 (7)	−0.0034 (6)	−0.0057 (7)
C27	0.0422 (9)	0.0370 (8)	0.0376 (8)	−0.0045 (7)	−0.0004 (7)	−0.0052 (7)
C28	0.0501 (10)	0.0479 (10)	0.0551 (10)	−0.0120 (8)	−0.0050 (8)	0.0003 (8)
C29	0.0589 (12)	0.0595 (12)	0.0696 (13)	−0.0179 (10)	0.0024 (10)	0.0133 (10)
C30	0.0727 (13)	0.0635 (13)	0.0547 (11)	−0.0132 (10)	0.0011 (10)	0.0217 (9)
C31	0.0640 (12)	0.0604 (12)	0.0470 (10)	−0.0051 (10)	−0.0118 (9)	0.0102 (9)
C32	0.0460 (9)	0.0405 (9)	0.0419 (9)	−0.0017 (7)	−0.0043 (7)	0.0007 (7)
C33	0.0463 (10)	0.0602 (11)	0.0542 (10)	−0.0065 (8)	−0.0162 (8)	0.0056 (9)
C34	0.0390 (9)	0.0572 (11)	0.0594 (11)	−0.0111 (8)	−0.0048 (8)	0.0063 (9)

O1—C4	1.3621 (17)	O5—C21	1.3616 (17)
O1—C3	1.4399 (17)	O5—C20	1.4386 (18)
O2—C6	1.3657 (18)	O6—C23	1.3570 (19)
O2—C3	1.4393 (18)	O6—C20	1.4286 (19)
O3—C4	1.2126 (18)	O7—C21	1.2143 (18)
O4—C6	1.2039 (19)	O8—C23	1.208 (2)
N1—C7	1.319 (2)	N2—C24	1.318 (2)
N1—C8	1.4232 (18)	N2—C25	1.4223 (19)
N1—H1	0.92 (2)	N2—H2	0.91 (2)
C1—C3	1.501 (2)	C18—C20	1.504 (2)
C1—H1A	0.9800	C18—H18A	0.9800
C1—H1B	0.9800	C18—H18B	0.9800
C1—H1C	0.9800	C18—H18C	0.9800
C2—C3	1.508 (2)	C19—C20	1.502 (2)
C2—H2A	0.9800	C19—H19A	0.9800
C2—H2B	0.9800	C19—H19B	0.9800
C2—H2C	0.9800	C19—H19C	0.9800
C4—C5	1.432 (2)	C21—C22	1.432 (2)
C5—C7	1.374 (2)	C22—C24	1.377 (2)
C5—C6	1.452 (2)	C22—C23	1.450 (2)
C7—H7	0.9500	C24—H24	0.9500
C8—C9	1.369 (2)	C25—C26	1.362 (2)
C8—C17	1.405 (2)	C25—C34	1.413 (2)
C9—C10	1.418 (2)	C26—C27	1.414 (2)
C9—H9	0.9500	C26—H26	0.9500
C10—C15	1.415 (2)	C27—C28	1.413 (2)
C10—C11	1.416 (2)	C27—C32	1.418 (2)
C11—C12	1.368 (2)	C28—C29	1.366 (2)
C11—H11	0.9500	C28—H28	0.9500
C12—C13	1.398 (3)	C29—C30	1.400 (3)
C12—H12	0.9500	C29—H29	0.9500
C13—C14	1.357 (3)	C30—C31	1.357 (3)
C13—H13	0.9500	C30—H30	0.9500
C14—C15	1.420 (2)	C31—C32	1.420 (2)
C14—H14	0.9500	C31—H31	0.9500
C15—C16	1.406 (2)	C32—C33	1.410 (2)
C16—C17	1.362 (2)	C33—C34	1.359 (2)
C16—H16	0.9500	C33—H33	0.9500
C17—H17	0.9500	C34—H34	0.9500
C4—O1—C3	117.01 (11)	C21—O5—C20	117.93 (12)
C6—O2—C3	117.24 (12)	C23—O6—C20	118.76 (12)
C7—N1—C8	124.07 (15)	C24—N2—C25	124.62 (15)
C7—N1—H1	117.5 (13)	C24—N2—H2	117.8 (13)
C8—N1—H1	118.4 (13)	C25—N2—H2	117.6 (13)
C3—C1—H1A	109.5	C20—C18—H18A	109.5
C3—C1—H1B	109.5	C20—C18—H18B	109.5
H1A—C1—H1B	109.5	H18A—C18—H18B	109.5
C3—C1—H1C	109.5	C20—C18—H18C	109.5
H1A—C1—H1C	109.5	H18A—C18—H18C	109.5
H1B—C1—H1C	109.5	H18B—C18—H18C	109.5
C3—C2—H2A	109.5	C20—C19—H19A	109.5
C3—C2—H2B	109.5	C20—C19—H19B	109.5
H2A—C2—H2B	109.5	H19A—C19—H19B	109.5
C3—C2—H2C	109.5	C20—C19—H19C	109.5
H2A—C2—H2C	109.5	H19A—C19—H19C	109.5
H2B—C2—H2C	109.5	H19B—C19—H19C	109.5
O1—C3—O2	109.46 (12)	O6—C20—O5	110.64 (12)
O1—C3—C1	106.82 (13)	O6—C20—C19	110.09 (14)
O2—C3—C1	106.47 (13)	O5—C20—C19	109.23 (13)
O1—C3—C2	110.33 (12)	O6—C20—C18	105.89 (13)
O2—C3—C2	110.52 (13)	O5—C20—C18	106.83 (13)
C1—C3—C2	113.07 (14)	C19—C20—C18	114.08 (15)
O3—C4—O1	118.26 (14)	O7—C21—O5	117.95 (14)
O3—C4—C5	124.93 (14)	O7—C21—C22	125.19 (14)
O1—C4—C5	116.77 (13)	O5—C21—C22	116.78 (13)
C7—C5—C4	121.39 (14)	C24—C22—C21	121.87 (15)
C7—C5—C6	118.04 (15)	C24—C22—C23	117.21 (15)
C4—C5—C6	120.52 (14)	C21—C22—C23	120.61 (14)
O4—C6—O2	117.83 (15)	O8—C23—O6	117.59 (16)
O4—C6—C5	126.67 (15)	O8—C23—C22	126.17 (16)
O2—C6—C5	115.46 (14)	O6—C23—C22	116.19 (15)
N1—C7—C5	127.43 (16)	N2—C24—C22	127.68 (16)
N1—C7—H7	116.3	N2—C24—H24	116.2
C5—C7—H7	116.3	C22—C24—H24	116.2
C9—C8—C17	120.32 (14)	C26—C25—C34	119.89 (14)
C9—C8—N1	119.35 (14)	C26—C25—N2	119.13 (14)
C17—C8—N1	120.33 (14)	C34—C25—N2	120.96 (14)
C8—C9—C10	120.49 (14)	C25—C26—C27	121.14 (14)
C8—C9—H9	119.8	C25—C26—H26	119.4
C10—C9—H9	119.8	C27—C26—H26	119.4
C15—C10—C11	118.51 (14)	C28—C27—C26	122.14 (14)
C15—C10—C9	119.14 (14)	C28—C27—C32	118.80 (14)
C11—C10—C9	122.35 (15)	C26—C27—C32	119.04 (14)
C12—C11—C10	120.78 (17)	C29—C28—C27	120.60 (17)
C12—C11—H11	119.6	C29—C28—H28	119.7
C10—C11—H11	119.6	C27—C28—H28	119.7
C11—C12—C13	120.34 (18)	C28—C29—C30	120.53 (17)
C11—C12—H12	119.8	C28—C29—H29	119.7
C13—C12—H12	119.8	C30—C29—H29	119.7
C14—C13—C12	120.71 (16)	C31—C30—C29	120.61 (17)
C14—C13—H13	119.6	C31—C30—H30	119.7
C12—C13—H13	119.6	C29—C30—H30	119.7
C13—C14—C15	120.52 (17)	C30—C31—C32	120.60 (17)
C13—C14—H14	119.7	C30—C31—H31	119.7
C15—C14—H14	119.7	C32—C31—H31	119.7
C16—C15—C10	118.43 (14)	C33—C32—C27	118.13 (14)
C16—C15—C14	122.44 (15)	C33—C32—C31	122.99 (16)
C10—C15—C14	119.13 (15)	C27—C32—C31	118.86 (15)
C17—C16—C15	121.73 (15)	C34—C33—C32	121.85 (16)
C17—C16—H16	119.1	C34—C33—H33	119.1
C15—C16—H16	119.1	C32—C33—H33	119.1
C16—C17—C8	119.88 (15)	C33—C34—C25	119.93 (15)
C16—C17—H17	120.1	C33—C34—H34	120.0
C8—C17—H17	120.1	C25—C34—H34	120.0
C4—O1—C3—O2	−51.22 (17)	C23—O6—C20—O5	−47.53 (19)
C4—O1—C3—C1	−166.12 (14)	C23—O6—C20—C19	73.30 (18)
C4—O1—C3—C2	70.61 (17)	C23—O6—C20—C18	−162.94 (15)
C6—O2—C3—O1	52.86 (17)	C21—O5—C20—O6	47.95 (18)
C6—O2—C3—C1	167.99 (14)	C21—O5—C20—C19	−73.39 (18)
C6—O2—C3—C2	−68.85 (17)	C21—O5—C20—C18	162.76 (14)
C3—O1—C4—O3	−161.61 (15)	C20—O5—C21—O7	160.40 (14)
C3—O1—C4—C5	20.7 (2)	C20—O5—C21—C22	−22.6 (2)
O3—C4—C5—C7	10.6 (3)	O7—C21—C22—C24	−2.1 (3)
O1—C4—C5—C7	−171.89 (14)	O5—C21—C22—C24	−178.83 (14)
O3—C4—C5—C6	−166.65 (17)	O7—C21—C22—C23	171.31 (17)
O1—C4—C5—C6	10.8 (2)	O5—C21—C22—C23	−5.5 (2)
C3—O2—C6—O4	158.74 (16)	C20—O6—C23—O8	−161.02 (17)
C3—O2—C6—C5	−23.5 (2)	C20—O6—C23—C22	21.5 (2)
C7—C5—C6—O4	−9.3 (3)	C24—C22—C23—O8	2.6 (3)
C4—C5—C6—O4	168.11 (18)	C21—C22—C23—O8	−171.02 (19)
C7—C5—C6—O2	173.17 (14)	C24—C22—C23—O6	179.83 (15)
C4—C5—C6—O2	−9.4 (2)	C21—C22—C23—O6	6.2 (2)
C8—N1—C7—C5	173.10 (16)	C25—N2—C24—C22	179.14 (16)
C4—C5—C7—N1	−0.2 (3)	C21—C22—C24—N2	−3.1 (3)
C6—C5—C7—N1	177.14 (16)	C23—C22—C24—N2	−176.69 (16)
C7—N1—C8—C9	155.71 (16)	C24—N2—C25—C26	161.00 (16)
C7—N1—C8—C17	−25.2 (2)	C24—N2—C25—C34	−19.9 (2)
C17—C8—C9—C10	0.6 (2)	C34—C25—C26—C27	1.6 (2)
N1—C8—C9—C10	179.75 (14)	N2—C25—C26—C27	−179.29 (14)
C8—C9—C10—C15	−0.5 (2)	C25—C26—C27—C28	177.77 (16)
C8—C9—C10—C11	179.06 (16)	C25—C26—C27—C32	−0.3 (2)
C15—C10—C11—C12	−1.4 (3)	C26—C27—C28—C29	−177.48 (17)
C9—C10—C11—C12	179.07 (17)	C32—C27—C28—C29	0.6 (3)
C10—C11—C12—C13	0.3 (3)	C27—C28—C29—C30	−0.2 (3)
C11—C12—C13—C14	0.5 (3)	C28—C29—C30—C31	−0.4 (3)
C12—C13—C14—C15	−0.3 (3)	C29—C30—C31—C32	0.6 (3)
C11—C10—C15—C16	−179.17 (16)	C28—C27—C32—C33	−178.95 (16)
C9—C10—C15—C16	0.4 (2)	C26—C27—C32—C33	−0.8 (2)
C11—C10—C15—C14	1.6 (2)	C28—C27—C32—C31	−0.4 (2)
C9—C10—C15—C14	−178.87 (15)	C26—C27—C32—C31	177.72 (15)
C13—C14—C15—C16	−179.98 (17)	C30—C31—C32—C33	178.27 (19)
C13—C14—C15—C10	−0.7 (3)	C30—C31—C32—C27	−0.2 (3)
C10—C15—C16—C17	−0.5 (3)	C27—C32—C33—C34	0.6 (3)
C14—C15—C16—C17	178.76 (17)	C31—C32—C33—C34	−177.87 (18)
C15—C16—C17—C8	0.6 (3)	C32—C33—C34—C25	0.7 (3)
C9—C8—C17—C16	−0.7 (3)	C26—C25—C34—C33	−1.9 (3)
N1—C8—C17—C16	−179.82 (16)	N2—C25—C34—C33	179.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.92 (2)	2.11 (2)	2.7681 (18)	127.2 (16)
N1—H1···O7	0.92 (2)	2.35 (2)	3.184 (2)	150.9 (17)
N2—H2···O7	0.91 (2)	2.15 (2)	2.7858 (18)	126.7 (17)
N2—H2···O3	0.91 (2)	2.36 (2)	3.1893 (19)	152.9 (17)
C7—H7···O4	0.95	2.50	2.833 (2)	101
C14—H14···O4i	0.95	2.51	3.354 (2)	148
C24—H24···O8	0.95	2.45	2.804 (2)	102
C26—H26···O3	0.95	2.46	3.2569 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.92 (2)	2.11 (2)	2.7681 (18)	127.2 (16)
N1—H1⋯O7	0.92 (2)	2.35 (2)	3.184 (2)	150.9 (17)
N2—H2⋯O7	0.91 (2)	2.15 (2)	2.7858 (18)	126.7 (17)
N2—H2⋯O3	0.91 (2)	2.36 (2)	3.1893 (19)	152.9 (17)
C7—H7⋯O4	0.95	2.50	2.833 (2)	101
C14—H14⋯O4i	0.95	2.51	3.354 (2)	148
C24—H24⋯O8	0.95	2.45	2.804 (2)	102
C26—H26⋯O3	0.95	2.46	3.2569 (19)	142

Symmetry code: (i) .