Napropamide.

THE TITLE COMPOUND [SYSTEMATIC NAME: N,N-diethyl-2-(naphthalen-1-yl-oxy)propanamide], C17H21NO2, crystallizes with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the naphthalene ring systems and the amide groups are 88.1 (9) and 88.7 (3)°. Four C-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For the herbicidal effects of the title compound, see: Freeman (1986 ▶). For information on the synthesis of the title compound, see: Gless (1986 ▶). For a related crystal structure, see: Au-Yeung et al. (2009 ▶).

Experimental

Crystal data

C17H21NO2

M = 271.35

Monoclinic,

a = 9.8733 (3) Å

b = 10.7710 (4) Å

c = 14.1044 (5) Å

β = 97.943 (2)°

V = 1485.55 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.35 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.973, T max = 0.988

26573 measured reflections

3897 independent reflections

3297 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.083

S = 1.03

3897 reflections

367 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017947/sj5338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017947/sj5338Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017947/sj5338Isup3.cml

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

C17H21NO2	F(000) = 584
Mr = 271.35	Dx = 1.213 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9958 reflections
a = 9.8733 (3) Å	θ = 2.4–28.2°
b = 10.7710 (4) Å	µ = 0.08 mm−1
c = 14.1044 (5) Å	T = 173 K
β = 97.943 (2)°	Block, colourless
V = 1485.55 (9) Å3	0.35 × 0.18 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	3897 independent reflections
Radiation source: fine-focus sealed tube	3297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.973, Tmax = 0.988	k = −12→14
26573 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0333P)2 + 0.2525P] where P = (Fo2 + 2Fc2)/3
3897 reflections	(Δ/σ)max < 0.001
367 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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	0.64959 (13)	0.16746 (14)	−0.03108 (9)	0.0340 (3)
O2	0.66356 (17)	0.40562 (16)	0.14147 (11)	0.0447 (4)
O3	0.33269 (15)	0.94175 (15)	0.27007 (9)	0.0365 (4)
O4	0.10307 (16)	1.13370 (15)	0.37266 (11)	0.0410 (4)
N1	0.67648 (18)	0.20374 (17)	0.18196 (11)	0.0343 (4)
N2	0.07201 (18)	0.92770 (17)	0.35334 (11)	0.0328 (4)
C1	0.78359 (19)	0.1750 (2)	−0.04740 (12)	0.0285 (4)
C2	0.8753 (2)	0.2628 (2)	−0.00987 (13)	0.0335 (5)
H2	0.8471	0.3282	0.0282	0.040*
C3	1.0125 (2)	0.2560 (2)	−0.02794 (13)	0.0373 (5)
H3	1.0764	0.3169	−0.0015	0.045*
C4	1.0541 (2)	0.1635 (2)	−0.08256 (14)	0.0369 (5)
H4	1.1471	0.1593	−0.0927	0.044*
C5	0.9607 (2)	0.0737 (2)	−0.12436 (13)	0.0297 (4)
C6	0.9996 (2)	−0.0220 (2)	−0.18405 (14)	0.0365 (5)
H6	1.0921	−0.0277	−0.1952	0.044*
C7	0.9068 (2)	−0.1059 (2)	−0.22572 (15)	0.0398 (5)
H7	0.9348	−0.1690	−0.2659	0.048*
C8	0.7705 (2)	−0.0996 (2)	−0.20960 (15)	0.0386 (5)
H8	0.7064	−0.1584	−0.2391	0.046*
C9	0.7284 (2)	−0.0093 (2)	−0.15167 (13)	0.0323 (4)
H9	0.6355	−0.0062	−0.1412	0.039*
C10	0.8220 (2)	0.0790 (2)	−0.10762 (12)	0.0273 (4)
C11	0.5932 (2)	0.2710 (2)	0.01310 (14)	0.0361 (5)
H11	0.6113	0.3469	−0.0241	0.043*
C12	0.4395 (2)	0.2515 (3)	0.00062 (16)	0.0500 (7)
H12A	0.4039	0.2498	−0.0678	0.075*
H12B	0.3963	0.3196	0.0315	0.075*
H12C	0.4189	0.1725	0.0300	0.075*
C13	0.6490 (2)	0.2955 (2)	0.11836 (14)	0.0337 (5)
C14	0.6488 (2)	0.0708 (2)	0.16476 (16)	0.0409 (5)
H14A	0.5902	0.0607	0.1024	0.049*
H14B	0.5976	0.0384	0.2151	0.049*
C15	0.7780 (3)	−0.0051 (3)	0.16438 (17)	0.0506 (6)
H15A	0.8216	0.0173	0.1084	0.076*
H15B	0.7549	−0.0936	0.1616	0.076*
H15C	0.8411	0.0119	0.2229	0.076*
C16	0.7273 (2)	0.2395 (3)	0.28120 (14)	0.0436 (6)
H16A	0.7921	0.3095	0.2806	0.052*
H16B	0.7778	0.1687	0.3141	0.052*
C17	0.6128 (3)	0.2773 (3)	0.33670 (16)	0.0516 (7)
H17A	0.5676	0.3518	0.3077	0.077*
H17B	0.6507	0.2948	0.4033	0.077*
H17C	0.5461	0.2097	0.3350	0.077*
C18	0.4283 (2)	0.9270 (2)	0.34998 (13)	0.0304 (4)
C19	0.4394 (2)	1.0002 (2)	0.42959 (14)	0.0354 (5)
H19	0.3775	1.0670	0.4334	0.043*
C20	0.5439 (2)	0.9757 (2)	0.50642 (15)	0.0389 (5)
H20	0.5523	1.0273	0.5616	0.047*
C21	0.6324 (2)	0.8802 (2)	0.50295 (14)	0.0374 (5)
H21	0.7016	0.8654	0.5555	0.045*
C22	0.6222 (2)	0.8019 (2)	0.42105 (13)	0.0311 (4)
C23	0.7123 (2)	0.7017 (2)	0.41399 (15)	0.0363 (5)
H23	0.7823	0.6847	0.4656	0.044*
C24	0.7002 (2)	0.6289 (2)	0.33414 (16)	0.0396 (5)
H24	0.7624	0.5623	0.3305	0.048*
C25	0.5972 (2)	0.6514 (2)	0.25768 (15)	0.0392 (5)
H25	0.5897	0.6000	0.2025	0.047*
C26	0.5073 (2)	0.7470 (2)	0.26198 (14)	0.0347 (5)
H26	0.4367	0.7608	0.2101	0.042*
C27	0.5183 (2)	0.8257 (2)	0.34330 (13)	0.0287 (4)
C28	0.2398 (2)	1.0435 (2)	0.26756 (14)	0.0334 (5)
H28	0.2949	1.1204	0.2838	0.040*
C29	0.1716 (2)	1.0554 (2)	0.16425 (14)	0.0428 (6)
H29A	0.2415	1.0701	0.1225	0.064*
H29B	0.1074	1.1252	0.1590	0.064*
H29C	0.1221	0.9787	0.1448	0.064*
C30	0.1332 (2)	1.0349 (2)	0.33672 (13)	0.0308 (4)
C31	−0.0305 (2)	0.9321 (3)	0.41976 (15)	0.0430 (6)
H31A	−0.0973	0.8643	0.4034	0.052*
H31B	−0.0807	1.0117	0.4108	0.052*
C32	0.0295 (3)	0.9199 (3)	0.52358 (14)	0.0491 (6)
H32A	0.0645	0.8354	0.5358	0.074*
H32B	−0.0414	0.9368	0.5641	0.074*
H32C	0.1044	0.9795	0.5384	0.074*
C33	0.0882 (2)	0.8087 (2)	0.30606 (15)	0.0406 (5)
H33A	0.1411	0.8222	0.2522	0.049*
H33B	−0.0033	0.7774	0.2790	0.049*
C34	0.1596 (3)	0.7109 (2)	0.37179 (18)	0.0500 (6)
H34A	0.2475	0.7434	0.4027	0.075*
H34B	0.1754	0.6368	0.3345	0.075*
H34C	0.1023	0.6891	0.4207	0.075*

	U11	U22	U33	U12	U13	U23
O1	0.0290 (7)	0.0402 (9)	0.0339 (7)	0.0012 (7)	0.0085 (6)	−0.0103 (6)
O2	0.0540 (10)	0.0376 (10)	0.0447 (8)	0.0007 (8)	0.0144 (7)	−0.0084 (7)
O3	0.0372 (8)	0.0415 (9)	0.0296 (7)	0.0074 (7)	0.0008 (6)	−0.0029 (6)
O4	0.0492 (9)	0.0325 (9)	0.0410 (8)	0.0076 (8)	0.0058 (7)	0.0005 (7)
N1	0.0358 (9)	0.0380 (11)	0.0288 (8)	0.0021 (8)	0.0035 (7)	−0.0044 (8)
N2	0.0354 (10)	0.0329 (10)	0.0298 (8)	−0.0045 (8)	0.0035 (7)	0.0006 (8)
C1	0.0278 (10)	0.0350 (11)	0.0228 (8)	0.0022 (9)	0.0037 (7)	0.0007 (8)
C2	0.0393 (11)	0.0358 (12)	0.0255 (8)	−0.0017 (10)	0.0055 (8)	−0.0041 (8)
C3	0.0359 (11)	0.0457 (14)	0.0294 (10)	−0.0117 (10)	0.0016 (8)	0.0033 (10)
C4	0.0284 (10)	0.0504 (15)	0.0324 (10)	−0.0008 (10)	0.0059 (8)	0.0066 (10)
C5	0.0299 (10)	0.0344 (11)	0.0253 (9)	0.0048 (9)	0.0062 (7)	0.0053 (8)
C6	0.0374 (12)	0.0414 (13)	0.0327 (10)	0.0111 (11)	0.0119 (8)	0.0079 (9)
C7	0.0579 (15)	0.0311 (12)	0.0330 (10)	0.0103 (11)	0.0158 (10)	0.0015 (9)
C8	0.0498 (13)	0.0315 (12)	0.0342 (10)	−0.0028 (11)	0.0051 (9)	−0.0029 (9)
C9	0.0350 (11)	0.0326 (11)	0.0296 (9)	−0.0004 (10)	0.0055 (8)	0.0010 (9)
C10	0.0300 (10)	0.0307 (11)	0.0216 (8)	0.0031 (9)	0.0048 (7)	0.0037 (8)
C11	0.0370 (11)	0.0389 (13)	0.0333 (10)	0.0089 (10)	0.0079 (8)	−0.0023 (9)
C12	0.0352 (12)	0.0755 (19)	0.0383 (11)	0.0150 (13)	0.0021 (9)	−0.0107 (12)
C13	0.0287 (10)	0.0413 (13)	0.0325 (10)	0.0028 (10)	0.0095 (8)	−0.0055 (9)
C14	0.0443 (13)	0.0376 (13)	0.0410 (11)	−0.0058 (11)	0.0063 (10)	0.0001 (10)
C15	0.0575 (15)	0.0432 (15)	0.0491 (13)	0.0111 (13)	0.0002 (11)	−0.0011 (12)
C16	0.0463 (13)	0.0534 (15)	0.0297 (9)	0.0013 (12)	0.0007 (9)	−0.0041 (10)
C17	0.0572 (15)	0.0623 (18)	0.0384 (11)	−0.0106 (14)	0.0177 (10)	−0.0067 (12)
C18	0.0275 (10)	0.0353 (11)	0.0292 (9)	−0.0017 (9)	0.0061 (7)	0.0024 (9)
C19	0.0343 (11)	0.0387 (13)	0.0349 (10)	−0.0026 (10)	0.0105 (8)	−0.0051 (10)
C20	0.0380 (12)	0.0475 (14)	0.0318 (10)	−0.0073 (11)	0.0073 (9)	−0.0090 (10)
C21	0.0325 (11)	0.0506 (14)	0.0285 (10)	−0.0045 (11)	0.0021 (8)	0.0010 (9)
C22	0.0275 (10)	0.0363 (12)	0.0306 (9)	−0.0052 (9)	0.0079 (7)	0.0042 (9)
C23	0.0330 (11)	0.0400 (13)	0.0351 (10)	−0.0011 (10)	0.0021 (8)	0.0102 (10)
C24	0.0398 (12)	0.0334 (12)	0.0468 (12)	0.0043 (10)	0.0097 (10)	0.0057 (10)
C25	0.0458 (13)	0.0350 (13)	0.0372 (10)	0.0017 (11)	0.0067 (9)	−0.0042 (10)
C26	0.0361 (11)	0.0368 (12)	0.0304 (9)	0.0021 (10)	0.0022 (8)	0.0002 (9)
C27	0.0281 (10)	0.0324 (11)	0.0267 (9)	−0.0031 (9)	0.0072 (7)	0.0031 (8)
C28	0.0338 (11)	0.0313 (12)	0.0353 (10)	0.0006 (9)	0.0056 (8)	0.0034 (9)
C29	0.0485 (14)	0.0482 (15)	0.0316 (10)	0.0072 (12)	0.0047 (9)	0.0074 (10)
C30	0.0298 (11)	0.0340 (12)	0.0273 (9)	0.0037 (9)	−0.0010 (8)	0.0033 (9)
C31	0.0321 (12)	0.0571 (16)	0.0409 (11)	−0.0066 (11)	0.0089 (9)	0.0061 (11)
C32	0.0525 (16)	0.0614 (17)	0.0342 (11)	−0.0045 (14)	0.0092 (10)	0.0026 (12)
C33	0.0489 (13)	0.0338 (12)	0.0376 (11)	−0.0094 (11)	0.0008 (9)	−0.0059 (10)
C34	0.0729 (17)	0.0295 (12)	0.0474 (13)	−0.0043 (12)	0.0074 (12)	−0.0008 (11)

O1—C1	1.376 (2)	C16—C17	1.517 (3)
O1—C11	1.428 (3)	C16—H16A	0.9900
O2—C13	1.233 (3)	C16—H16B	0.9900
O3—C18	1.376 (2)	C17—H17A	0.9800
O3—C28	1.426 (3)	C17—H17B	0.9800
O4—C30	1.233 (3)	C17—H17C	0.9800
N1—C13	1.337 (3)	C18—C19	1.364 (3)
N1—C16	1.471 (3)	C18—C27	1.419 (3)
N1—C14	1.472 (3)	C19—C20	1.414 (3)
N2—C30	1.339 (3)	C19—H19	0.9500
N2—C33	1.464 (3)	C20—C21	1.355 (3)
N2—C31	1.472 (3)	C20—H20	0.9500
C1—C2	1.364 (3)	C21—C22	1.422 (3)
C1—C10	1.423 (3)	C21—H21	0.9500
C2—C3	1.414 (3)	C22—C23	1.411 (3)
C2—H2	0.9500	C22—C27	1.418 (3)
C3—C4	1.357 (3)	C23—C24	1.364 (3)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.408 (3)	C24—C25	1.398 (3)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.417 (3)	C25—C26	1.366 (3)
C5—C10	1.423 (3)	C25—H25	0.9500
C6—C7	1.361 (3)	C26—C27	1.418 (3)
C6—H6	0.9500	C26—H26	0.9500
C7—C8	1.397 (3)	C28—C29	1.524 (3)
C7—H7	0.9500	C28—C30	1.534 (3)
C8—C9	1.371 (3)	C28—H28	1.0000
C8—H8	0.9500	C29—H29A	0.9800
C9—C10	1.409 (3)	C29—H29B	0.9800
C9—H9	0.9500	C29—H29C	0.9800
C11—C12	1.519 (3)	C31—C32	1.507 (3)
C11—C13	1.533 (3)	C31—H31A	0.9900
C11—H11	1.0000	C31—H31B	0.9900
C12—H12A	0.9800	C32—H32A	0.9800
C12—H12B	0.9800	C32—H32B	0.9800
C12—H12C	0.9800	C32—H32C	0.9800
C14—C15	1.516 (3)	C33—C34	1.512 (3)
C14—H14A	0.9900	C33—H33A	0.9900
C14—H14B	0.9900	C33—H33B	0.9900
C15—H15A	0.9800	C34—H34A	0.9800
C15—H15B	0.9800	C34—H34B	0.9800
C15—H15C	0.9800	C34—H34C	0.9800
C1—O1—C11	117.92 (16)	H17A—C17—H17B	109.5
C18—O3—C28	118.37 (16)	C16—C17—H17C	109.5
C13—N1—C16	117.11 (19)	H17A—C17—H17C	109.5
C13—N1—C14	126.36 (17)	H17B—C17—H17C	109.5
C16—N1—C14	116.26 (18)	C19—C18—O3	125.1 (2)
C30—N2—C33	126.51 (17)	C19—C18—C27	121.31 (18)
C30—N2—C31	116.8 (2)	O3—C18—C27	113.55 (17)
C33—N2—C31	116.49 (19)	C18—C19—C20	119.3 (2)
C2—C1—O1	125.30 (18)	C18—C19—H19	120.3
C2—C1—C10	121.22 (17)	C20—C19—H19	120.3
O1—C1—C10	113.47 (17)	C21—C20—C19	121.3 (2)
C1—C2—C3	119.63 (19)	C21—C20—H20	119.3
C1—C2—H2	120.2	C19—C20—H20	119.3
C3—C2—H2	120.2	C20—C21—C22	120.38 (19)
C4—C3—C2	120.9 (2)	C20—C21—H21	119.8
C4—C3—H3	119.6	C22—C21—H21	119.8
C2—C3—H3	119.6	C23—C22—C27	118.64 (19)
C3—C4—C5	120.68 (19)	C23—C22—C21	122.44 (19)
C3—C4—H4	119.7	C27—C22—C21	118.9 (2)
C5—C4—H4	119.7	C24—C23—C22	121.0 (2)
C4—C5—C6	122.21 (19)	C24—C23—H23	119.5
C4—C5—C10	119.48 (18)	C22—C23—H23	119.5
C6—C5—C10	118.30 (19)	C23—C24—C25	120.6 (2)
C7—C6—C5	121.2 (2)	C23—C24—H24	119.7
C7—C6—H6	119.4	C25—C24—H24	119.7
C5—C6—H6	119.4	C26—C25—C24	120.3 (2)
C6—C7—C8	120.2 (2)	C26—C25—H25	119.9
C6—C7—H7	119.9	C24—C25—H25	119.9
C8—C7—H7	119.9	C25—C26—C27	120.57 (19)
C9—C8—C7	120.7 (2)	C25—C26—H26	119.7
C9—C8—H8	119.7	C27—C26—H26	119.7
C7—C8—H8	119.7	C22—C27—C26	118.95 (19)
C8—C9—C10	120.5 (2)	C22—C27—C18	118.71 (18)
C8—C9—H9	119.8	C26—C27—C18	122.33 (17)
C10—C9—H9	119.8	O3—C28—C29	106.63 (17)
C9—C10—C5	119.18 (18)	O3—C28—C30	115.67 (17)
C9—C10—C1	122.77 (17)	C29—C28—C30	111.22 (17)
C5—C10—C1	118.05 (18)	O3—C28—H28	107.7
O1—C11—C12	106.54 (18)	C29—C28—H28	107.7
O1—C11—C13	116.58 (17)	C30—C28—H28	107.7
C12—C11—C13	110.83 (16)	C28—C29—H29A	109.5
O1—C11—H11	107.5	C28—C29—H29B	109.5
C12—C11—H11	107.5	H29A—C29—H29B	109.5
C13—C11—H11	107.5	C28—C29—H29C	109.5
C11—C12—H12A	109.5	H29A—C29—H29C	109.5
C11—C12—H12B	109.5	H29B—C29—H29C	109.5
H12A—C12—H12B	109.5	O4—C30—N2	122.14 (19)
C11—C12—H12C	109.5	O4—C30—C28	115.79 (19)
H12A—C12—H12C	109.5	N2—C30—C28	121.99 (18)
H12B—C12—H12C	109.5	N2—C31—C32	113.77 (18)
O2—C13—N1	121.89 (19)	N2—C31—H31A	108.8
O2—C13—C11	115.7 (2)	C32—C31—H31A	108.8
N1—C13—C11	122.3 (2)	N2—C31—H31B	108.8
N1—C14—C15	112.8 (2)	C32—C31—H31B	108.8
N1—C14—H14A	109.0	H31A—C31—H31B	107.7
C15—C14—H14A	109.0	C31—C32—H32A	109.5
N1—C14—H14B	109.0	C31—C32—H32B	109.5
C15—C14—H14B	109.0	H32A—C32—H32B	109.5
H14A—C14—H14B	107.8	C31—C32—H32C	109.5
C14—C15—H15A	109.5	H32A—C32—H32C	109.5
C14—C15—H15B	109.5	H32B—C32—H32C	109.5
H15A—C15—H15B	109.5	N2—C33—C34	113.70 (18)
C14—C15—H15C	109.5	N2—C33—H33A	108.8
H15A—C15—H15C	109.5	C34—C33—H33A	108.8
H15B—C15—H15C	109.5	N2—C33—H33B	108.8
N1—C16—C17	112.36 (19)	C34—C33—H33B	108.8
N1—C16—H16A	109.1	H33A—C33—H33B	107.7
C17—C16—H16A	109.1	C33—C34—H34A	109.5
N1—C16—H16B	109.1	C33—C34—H34B	109.5
C17—C16—H16B	109.1	H34A—C34—H34B	109.5
H16A—C16—H16B	107.9	C33—C34—H34C	109.5
C16—C17—H17A	109.5	H34A—C34—H34C	109.5
C16—C17—H17B	109.5	H34B—C34—H34C	109.5
C11—O1—C1—C2	12.6 (3)	C28—O3—C18—C19	2.2 (3)
C11—O1—C1—C10	−168.54 (16)	C28—O3—C18—C27	−177.86 (17)
O1—C1—C2—C3	176.36 (18)	O3—C18—C19—C20	−179.1 (2)
C10—C1—C2—C3	−2.4 (3)	C27—C18—C19—C20	0.9 (3)
C1—C2—C3—C4	0.3 (3)	C18—C19—C20—C21	−0.7 (3)
C2—C3—C4—C5	1.4 (3)	C19—C20—C21—C22	0.2 (3)
C3—C4—C5—C6	178.1 (2)	C20—C21—C22—C23	179.8 (2)
C3—C4—C5—C10	−1.1 (3)	C20—C21—C22—C27	0.1 (3)
C4—C5—C6—C7	−178.3 (2)	C27—C22—C23—C24	0.1 (3)
C10—C5—C6—C7	1.0 (3)	C21—C22—C23—C24	−179.6 (2)
C5—C6—C7—C8	−0.5 (3)	C22—C23—C24—C25	−0.6 (3)
C6—C7—C8—C9	−0.1 (3)	C23—C24—C25—C26	0.1 (3)
C7—C8—C9—C10	0.2 (3)	C24—C25—C26—C27	0.9 (3)
C8—C9—C10—C5	0.3 (3)	C23—C22—C27—C26	0.9 (3)
C8—C9—C10—C1	179.57 (19)	C21—C22—C27—C26	−179.40 (19)
C4—C5—C10—C9	178.36 (18)	C23—C22—C27—C18	−179.53 (18)
C6—C5—C10—C9	−0.9 (3)	C21—C22—C27—C18	0.2 (3)
C4—C5—C10—C1	−0.9 (3)	C25—C26—C27—C22	−1.4 (3)
C6—C5—C10—C1	179.84 (17)	C25—C26—C27—C18	179.0 (2)
C2—C1—C10—C9	−176.56 (18)	C19—C18—C27—C22	−0.7 (3)
O1—C1—C10—C9	4.5 (3)	O3—C18—C27—C22	179.40 (17)
C2—C1—C10—C5	2.7 (3)	C19—C18—C27—C26	178.9 (2)
O1—C1—C10—C5	−176.23 (16)	O3—C18—C27—C26	−1.1 (3)
C1—O1—C11—C12	166.67 (16)	C18—O3—C28—C29	166.45 (18)
C1—O1—C11—C13	−69.0 (2)	C18—O3—C28—C30	−69.3 (2)
C16—N1—C13—O2	−1.0 (3)	C33—N2—C30—O4	172.35 (19)
C14—N1—C13—O2	172.9 (2)	C31—N2—C30—O4	−2.1 (3)
C16—N1—C13—C11	−178.96 (18)	C33—N2—C30—C28	−4.3 (3)
C14—N1—C13—C11	−5.1 (3)	C31—N2—C30—C28	−178.82 (17)
O1—C11—C13—O2	141.9 (2)	O3—C28—C30—O4	143.88 (18)
C12—C11—C13—O2	−96.0 (2)	C29—C28—C30—O4	−94.3 (2)
O1—C11—C13—N1	−39.9 (3)	O3—C28—C30—N2	−39.2 (3)
C12—C11—C13—N1	82.1 (3)	C29—C28—C30—N2	82.6 (2)
C13—N1—C14—C15	110.4 (2)	C30—N2—C31—C32	−85.6 (3)
C16—N1—C14—C15	−75.7 (3)	C33—N2—C31—C32	99.4 (3)
C13—N1—C16—C17	81.5 (3)	C30—N2—C33—C34	112.8 (2)
C14—N1—C16—C17	−93.0 (3)	C31—N2—C33—C34	−72.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O2	0.95	2.41	3.228 (3)	144
C6—H6···O2i	0.95	2.53	3.388 (3)	150
C7—H7···O4ii	0.95	2.60	3.481 (3)	154
C23—H23···O4iii	0.95	2.46	3.376 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯O2	0.95	2.41	3.228 (3)	144
C6—H6⋯O2i	0.95	2.53	3.388 (3)	150
C7—H7⋯O4ii	0.95	2.60	3.481 (3)	154
C23—H23⋯O4iii	0.95	2.46	3.376 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) .