N-[(2-Hydr-oxy-1-naphth-yl)(2-hydroxy-phen-yl)meth-yl]acetamide.

In the asymmetric unit of the title compound, C(19)H(17)NO(3), there are two crystallographically independent mol-ecules, which are connected to each other by O-H⋯O hydrogen bonds, forming mol-ecular chains as well as cyclic centrosymmetric R(2) (2)(16) dimers.

Related literature

For background literature, see: Barker et al. (2008 ▶); Gade (2002 ▶); Linton & Hamilton (1997 ▶); Valeur & Leray (2000 ▶); Wabnitz & Spencer (2002 ▶). For related structures, see: Gowda et al. (2000 ▶, 2006 ▶, 2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Fun et al. (2008 ▶).

Experimental

Crystal data

C19H17NO3

M = 307.34

Monoclinic,

a = 21.286 (5) Å

b = 17.9288 (4) Å

c = 19.524 (7) Å

β = 121.428 (1)°

V = 6358 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.980, T max = 0.986

33278 measured reflections

6464 independent reflections

4384 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.146

S = 1.02

6464 reflections

417 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007983/pv2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007983/pv2141Isup2.hkl

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

C19H17NO3	F(000) = 2592
Mr = 307.34	Dx = 1.284 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6464 reflections
a = 21.286 (5) Å	θ = 2.5–25°
b = 17.9288 (4) Å	µ = 0.09 mm−1
c = 19.524 (7) Å	T = 293 K
β = 121.428 (1)°	Prism, colourless
V = 6358 (3) Å3	0.20 × 0.16 × 0.16 mm
Z = 16

Bruker Kappa APEXII CCD diffractometer	6464 independent reflections
Radiation source: fine-focus sealed tube	4384 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −26→26
Tmin = 0.980, Tmax = 0.986	k = −22→22
33278 measured reflections	l = −24→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0747P)2 + 2.6626P] where P = (Fo2 + 2Fc2)/3
6464 reflections	(Δ/σ)max = 0.005
417 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.49 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	0.05068 (7)	0.50195 (8)	0.59220 (8)	0.0556 (4)
H1	0.0080	0.5100	0.5793	0.083*
O2	0.30227 (7)	0.59048 (8)	0.70861 (10)	0.0655 (4)
H2	0.3361	0.6207	0.7274	0.098*
O3	0.09894 (7)	0.46622 (7)	0.47788 (7)	0.0427 (3)
N1	0.17949 (8)	0.53425 (8)	0.58664 (9)	0.0413 (4)
H1A	0.2011	0.5768	0.6017	0.050*
C1	0.09638 (10)	0.51566 (10)	0.67223 (11)	0.0415 (4)
C2	0.07009 (11)	0.53887 (11)	0.72002 (13)	0.0531 (5)
H2A	0.0200	0.5475	0.6975	0.064*
C3	0.11779 (12)	0.54928 (13)	0.80092 (14)	0.0619 (6)
H3	0.1000	0.5648	0.8332	0.074*
C4	0.19150 (13)	0.53670 (14)	0.83396 (13)	0.0659 (6)
H4	0.2238	0.5436	0.8887	0.079*
C5	0.21785 (11)	0.51384 (12)	0.78609 (12)	0.0533 (5)
H5	0.2680	0.5051	0.8092	0.064*
C6	0.17118 (9)	0.50360 (10)	0.70431 (11)	0.0391 (4)
C7	0.19871 (9)	0.47856 (9)	0.65004 (10)	0.0376 (4)
H7	0.1727	0.4323	0.6237	0.045*
C8	0.28056 (9)	0.46165 (10)	0.69505 (11)	0.0399 (4)
C9	0.33020 (10)	0.52005 (11)	0.72284 (12)	0.0473 (5)
C10	0.40660 (11)	0.50776 (14)	0.76622 (13)	0.0600 (6)
H10	0.4390	0.5479	0.7834	0.072*
C11	0.43294 (11)	0.43680 (15)	0.78296 (13)	0.0641 (6)
H11	0.4836	0.4290	0.8120	0.077*
C12	0.38526 (12)	0.37479 (13)	0.75730 (12)	0.0552 (5)
C13	0.30753 (10)	0.38715 (11)	0.71243 (10)	0.0431 (4)
C14	0.26164 (12)	0.32330 (11)	0.68782 (12)	0.0531 (5)
H14	0.2108	0.3296	0.6590	0.064*
C15	0.28989 (16)	0.25316 (13)	0.70521 (14)	0.0739 (7)
H15	0.2584	0.2123	0.6876	0.089*
C16	0.36600 (18)	0.24206 (16)	0.74933 (16)	0.0850 (9)
H16	0.3850	0.1939	0.7615	0.102*
C17	0.41189 (15)	0.30083 (17)	0.77423 (14)	0.0747 (8)
H17	0.4624	0.2926	0.8033	0.090*
C18	0.13247 (10)	0.52537 (10)	0.50919 (11)	0.0398 (4)
C19	0.12036 (14)	0.59206 (12)	0.45734 (14)	0.0709 (7)
H19A	0.1426	0.5835	0.4261	0.106*
H19B	0.1422	0.6352	0.4906	0.106*
H19C	0.0685	0.6002	0.4221	0.106*
O1A	−0.04220 (8)	0.82226 (9)	0.16047 (8)	0.0572 (4)
H1A1	0.0018	0.8190	0.1765	0.086*
O2A	0.05897 (8)	0.65781 (7)	0.02450 (8)	0.0532 (4)
H2A1	0.0688	0.6224	0.0051	0.080*
O3A	0.11589 (7)	0.79276 (7)	0.26185 (8)	0.0472 (3)
N1A	0.06323 (8)	0.72763 (8)	0.14574 (8)	0.0364 (3)
H1A2	0.0553	0.6835	0.1257	0.044*
C1A	−0.08229 (10)	0.80834 (10)	0.08044 (12)	0.0444 (4)
C2A	−0.15812 (11)	0.80967 (13)	0.03873 (14)	0.0591 (6)
H2A2	−0.1826	0.8196	0.0656	0.071*
C3A	−0.19743 (13)	0.79645 (16)	−0.04221 (16)	0.0768 (8)
H3A	−0.2486	0.7973	−0.0700	0.092*
C4A	−0.16199 (13)	0.78190 (18)	−0.08270 (15)	0.0820 (8)
H4A	−0.1888	0.7730	−0.1377	0.098*
C5A	−0.08569 (12)	0.78056 (14)	−0.04061 (12)	0.0613 (6)
H5A	−0.0617	0.7708	−0.0680	0.074*
C6A	−0.04459 (10)	0.79339 (10)	0.04089 (11)	0.0412 (4)
C7A	0.03910 (9)	0.79041 (9)	0.08923 (10)	0.0361 (4)
H7A	0.0562	0.8361	0.1214	0.043*
C8A	0.07419 (9)	0.78832 (9)	0.03854 (10)	0.0361 (4)
C9A	0.08438 (10)	0.72246 (10)	0.00967 (11)	0.0421 (4)
C10A	0.11902 (12)	0.72005 (12)	−0.03502 (12)	0.0547 (5)
H10A	0.1268	0.6744	−0.0520	0.066*
C11A	0.14087 (12)	0.78344 (13)	−0.05326 (12)	0.0573 (6)
H11A	0.1644	0.7810	−0.0821	0.069*
C12A	0.12871 (10)	0.85341 (11)	−0.02947 (11)	0.0471 (5)
C13A	0.09502 (9)	0.85622 (10)	0.01715 (10)	0.0385 (4)
C14A	0.08239 (10)	0.92775 (10)	0.03835 (12)	0.0478 (5)
H14A	0.0605	0.9315	0.0689	0.057*
C15A	0.10157 (12)	0.99152 (12)	0.01502 (14)	0.0618 (6)
H15A	0.0927	1.0378	0.0299	0.074*
C16A	0.13439 (13)	0.98752 (14)	−0.03111 (15)	0.0678 (7)
H16A	0.1471	1.0310	−0.0471	0.081*
C17A	0.14749 (12)	0.92046 (14)	−0.05222 (13)	0.0609 (6)
H17A	0.1695	0.9183	−0.0826	0.073*
C18A	0.09592 (9)	0.73285 (9)	0.22438 (10)	0.0376 (4)
C19A	0.10774 (14)	0.66185 (12)	0.26910 (13)	0.0664 (6)
H19D	0.1576	0.6455	0.2912	0.100*
H19E	0.0746	0.6245	0.2332	0.100*
H19F	0.0986	0.6698	0.3118	0.100*

	U11	U22	U33	U12	U13	U23
O1	0.0317 (7)	0.0809 (10)	0.0451 (8)	0.0032 (6)	0.0138 (6)	−0.0079 (7)
O2	0.0455 (8)	0.0528 (9)	0.0865 (11)	−0.0171 (6)	0.0263 (8)	−0.0101 (8)
O3	0.0459 (7)	0.0437 (7)	0.0373 (7)	−0.0037 (5)	0.0210 (6)	0.0021 (5)
N1	0.0413 (8)	0.0384 (8)	0.0412 (9)	−0.0073 (6)	0.0195 (7)	0.0029 (6)
C1	0.0359 (10)	0.0454 (10)	0.0392 (10)	−0.0024 (7)	0.0170 (8)	−0.0011 (8)
C2	0.0417 (11)	0.0628 (13)	0.0575 (13)	0.0017 (9)	0.0278 (10)	−0.0055 (10)
C3	0.0575 (14)	0.0827 (16)	0.0557 (14)	−0.0054 (11)	0.0367 (12)	−0.0149 (11)
C4	0.0558 (14)	0.0982 (18)	0.0403 (12)	−0.0084 (12)	0.0226 (11)	−0.0121 (11)
C5	0.0383 (10)	0.0776 (14)	0.0405 (12)	−0.0030 (9)	0.0181 (9)	−0.0024 (10)
C6	0.0347 (9)	0.0431 (9)	0.0384 (10)	−0.0037 (7)	0.0183 (8)	0.0017 (8)
C7	0.0344 (9)	0.0394 (9)	0.0353 (10)	−0.0045 (7)	0.0156 (8)	0.0017 (7)
C8	0.0336 (9)	0.0510 (10)	0.0345 (10)	−0.0024 (7)	0.0173 (8)	−0.0013 (8)
C9	0.0376 (10)	0.0579 (12)	0.0466 (12)	−0.0060 (8)	0.0221 (9)	−0.0049 (9)
C10	0.0359 (11)	0.0898 (17)	0.0515 (13)	−0.0125 (11)	0.0208 (10)	−0.0118 (11)
C11	0.0339 (11)	0.108 (2)	0.0452 (13)	0.0087 (11)	0.0170 (9)	−0.0039 (12)
C12	0.0496 (12)	0.0800 (15)	0.0343 (11)	0.0183 (11)	0.0207 (9)	0.0040 (10)
C13	0.0440 (10)	0.0565 (11)	0.0288 (9)	0.0069 (8)	0.0190 (8)	0.0016 (8)
C14	0.0631 (13)	0.0502 (11)	0.0416 (11)	0.0043 (9)	0.0243 (10)	0.0037 (9)
C15	0.103 (2)	0.0525 (13)	0.0569 (15)	0.0120 (12)	0.0349 (14)	0.0057 (11)
C16	0.116 (2)	0.0699 (17)	0.0615 (16)	0.0430 (17)	0.0412 (17)	0.0142 (14)
C17	0.0735 (16)	0.096 (2)	0.0478 (14)	0.0407 (15)	0.0266 (12)	0.0112 (13)
C18	0.0392 (10)	0.0421 (10)	0.0400 (11)	0.0004 (7)	0.0220 (8)	0.0062 (8)
C19	0.0904 (17)	0.0539 (13)	0.0561 (14)	−0.0071 (11)	0.0296 (13)	0.0165 (11)
O1A	0.0482 (8)	0.0822 (10)	0.0491 (9)	0.0035 (7)	0.0308 (7)	−0.0040 (7)
O2A	0.0785 (10)	0.0377 (7)	0.0558 (9)	−0.0008 (6)	0.0437 (8)	−0.0059 (6)
O3A	0.0497 (8)	0.0510 (8)	0.0430 (8)	−0.0150 (6)	0.0257 (6)	−0.0112 (6)
N1A	0.0441 (8)	0.0343 (7)	0.0327 (8)	0.0001 (6)	0.0212 (7)	−0.0004 (6)
C1A	0.0443 (11)	0.0470 (10)	0.0448 (11)	0.0062 (8)	0.0253 (9)	0.0098 (8)
C2A	0.0468 (12)	0.0752 (15)	0.0633 (15)	0.0115 (10)	0.0343 (11)	0.0171 (11)
C3A	0.0406 (12)	0.117 (2)	0.0626 (16)	0.0098 (12)	0.0201 (12)	0.0232 (14)
C4A	0.0492 (14)	0.140 (3)	0.0415 (13)	0.0071 (14)	0.0133 (11)	0.0125 (14)
C5A	0.0530 (13)	0.0939 (17)	0.0376 (12)	0.0075 (11)	0.0242 (10)	0.0092 (11)
C6A	0.0427 (10)	0.0449 (10)	0.0398 (10)	0.0053 (7)	0.0241 (8)	0.0085 (8)
C7A	0.0433 (10)	0.0335 (8)	0.0362 (10)	0.0019 (7)	0.0241 (8)	0.0024 (7)
C8A	0.0378 (9)	0.0396 (9)	0.0314 (9)	0.0033 (7)	0.0184 (8)	0.0018 (7)
C9A	0.0482 (11)	0.0436 (10)	0.0361 (10)	0.0038 (8)	0.0231 (9)	0.0012 (8)
C10A	0.0682 (14)	0.0587 (13)	0.0486 (12)	0.0087 (10)	0.0384 (11)	−0.0051 (10)
C11A	0.0640 (14)	0.0759 (15)	0.0486 (13)	0.0025 (11)	0.0410 (11)	−0.0010 (10)
C12A	0.0430 (11)	0.0617 (12)	0.0361 (10)	−0.0028 (8)	0.0203 (9)	0.0056 (9)
C13A	0.0350 (9)	0.0464 (10)	0.0310 (9)	−0.0001 (7)	0.0151 (8)	0.0038 (7)
C14A	0.0511 (11)	0.0443 (10)	0.0497 (12)	0.0021 (8)	0.0275 (10)	0.0048 (9)
C15A	0.0647 (14)	0.0450 (11)	0.0678 (15)	−0.0017 (9)	0.0291 (12)	0.0083 (10)
C16A	0.0716 (15)	0.0637 (15)	0.0650 (15)	−0.0153 (11)	0.0335 (13)	0.0165 (12)
C17A	0.0608 (13)	0.0790 (16)	0.0479 (13)	−0.0136 (11)	0.0319 (11)	0.0091 (11)
C18A	0.0360 (9)	0.0429 (10)	0.0353 (10)	−0.0027 (7)	0.0194 (8)	−0.0010 (8)
C19A	0.0892 (17)	0.0554 (13)	0.0411 (12)	−0.0012 (11)	0.0245 (12)	0.0092 (10)

O1—C1	1.365 (2)	O1A—H1A1	0.8200
O1—H1	0.8200	O2A—C9A	1.372 (2)
O2—C9	1.361 (2)	O2A—H2A1	0.8200
O2—H2	0.8200	O3A—C18A	1.243 (2)
O3—C18	1.246 (2)	N1A—C18A	1.318 (2)
N1—C18	1.317 (2)	N1A—C7A	1.469 (2)
N1—C7	1.473 (2)	N1A—H1A2	0.8600
N1—H1A	0.8600	C1A—C2A	1.378 (3)
C1—C2	1.379 (3)	C1A—C6A	1.400 (3)
C1—C6	1.391 (2)	C2A—C3A	1.369 (3)
C2—C3	1.374 (3)	C2A—H2A2	0.9300
C2—H2A	0.9300	C3A—C4A	1.373 (4)
C3—C4	1.369 (3)	C3A—H3A	0.9300
C3—H3	0.9300	C4A—C5A	1.386 (3)
C4—C5	1.380 (3)	C4A—H4A	0.9300
C4—H4	0.9300	C5A—C6A	1.378 (3)
C5—C6	1.384 (3)	C5A—H5A	0.9300
C5—H5	0.9300	C6A—C7A	1.521 (2)
C6—C7	1.521 (3)	C7A—C8A	1.520 (2)
C7—C8	1.518 (2)	C7A—H7A	0.9800
C7—H7	0.9800	C8A—C9A	1.374 (2)
C8—C9	1.382 (3)	C8A—C13A	1.430 (2)
C8—C13	1.423 (3)	C9A—C10A	1.406 (3)
C9—C10	1.405 (3)	C10A—C11A	1.344 (3)
C10—C11	1.360 (3)	C10A—H10A	0.9300
C10—H10	0.9300	C11A—C12A	1.408 (3)
C11—C12	1.410 (3)	C11A—H11A	0.9300
C11—H11	0.9300	C12A—C17A	1.410 (3)
C12—C17	1.412 (3)	C12A—C13A	1.423 (3)
C12—C13	1.429 (3)	C13A—C14A	1.416 (3)
C13—C14	1.416 (3)	C14A—C15A	1.370 (3)
C14—C15	1.358 (3)	C14A—H14A	0.9300
C14—H14	0.9300	C15A—C16A	1.400 (4)
C15—C16	1.397 (4)	C15A—H15A	0.9300
C15—H15	0.9300	C16A—C17A	1.347 (3)
C16—C17	1.344 (4)	C16A—H16A	0.9300
C16—H16	0.9300	C17A—H17A	0.9300
C17—H17	0.9300	C18A—O3A	1.243 (2)
C18—O3	1.246 (2)	C18A—O3A	1.243 (2)
C18—C19	1.499 (3)	C18A—C19A	1.489 (3)
C19—H19A	0.9600	C19A—H19D	0.9600
C19—H19B	0.9600	C19A—H19E	0.9600
C19—H19C	0.9600	C19A—H19F	0.9600
O1A—C1A	1.357 (2)
C1—O1—H1	109.5	C9A—O2A—H2A1	109.5
C9—O2—H2	109.5	C18A—N1A—C7A	125.89 (14)
C18—N1—C7	126.49 (14)	C18A—N1A—H1A2	117.1
C18—N1—H1A	116.8	C7A—N1A—H1A2	117.1
C7—N1—H1A	116.8	O1A—C1A—C2A	121.13 (18)
O1—C1—C2	122.04 (16)	O1A—C1A—C6A	118.25 (16)
O1—C1—C6	116.91 (17)	C2A—C1A—C6A	120.61 (19)
C2—C1—C6	121.03 (17)	C3A—C2A—C1A	120.1 (2)
C3—C2—C1	120.10 (18)	C3A—C2A—H2A2	119.9
C3—C2—H2A	120.0	C1A—C2A—H2A2	119.9
C1—C2—H2A	120.0	C2A—C3A—C4A	120.6 (2)
C4—C3—C2	119.9 (2)	C2A—C3A—H3A	119.7
C4—C3—H3	120.1	C4A—C3A—H3A	119.7
C2—C3—H3	120.1	C3A—C4A—C5A	119.2 (2)
C3—C4—C5	120.1 (2)	C3A—C4A—H4A	120.4
C3—C4—H4	120.0	C5A—C4A—H4A	120.4
C5—C4—H4	120.0	C6A—C5A—C4A	121.6 (2)
C6—C5—C4	121.34 (19)	C6A—C5A—H5A	119.2
C6—C5—H5	119.3	C4A—C5A—H5A	119.2
C4—C5—H5	119.3	C5A—C6A—C1A	117.88 (17)
C5—C6—C1	117.60 (18)	C5A—C6A—C7A	122.95 (17)
C5—C6—C7	122.49 (16)	C1A—C6A—C7A	119.16 (16)
C1—C6—C7	119.90 (16)	N1A—C7A—C8A	111.85 (13)
N1—C7—C8	110.73 (14)	N1A—C7A—C6A	109.32 (13)
N1—C7—C6	110.26 (14)	C8A—C7A—C6A	114.26 (14)
C8—C7—C6	113.48 (14)	N1A—C7A—H7A	107.0
N1—C7—H7	107.4	C8A—C7A—H7A	107.0
C8—C7—H7	107.4	C6A—C7A—H7A	107.0
C6—C7—H7	107.4	C9A—C8A—C13A	118.19 (16)
C9—C8—C13	119.13 (17)	C9A—C8A—C7A	121.65 (15)
C9—C8—C7	119.21 (16)	C13A—C8A—C7A	120.11 (15)
C13—C8—C7	121.61 (15)	O2A—C9A—C8A	118.40 (16)
O2—C9—C8	117.37 (16)	O2A—C9A—C10A	119.78 (16)
O2—C9—C10	120.90 (18)	C8A—C9A—C10A	121.81 (17)
C8—C9—C10	121.71 (19)	C11A—C10A—C9A	120.26 (18)
C11—C10—C9	119.6 (2)	C11A—C10A—H10A	119.9
C11—C10—H10	120.2	C9A—C10A—H10A	119.9
C9—C10—H10	120.2	C10A—C11A—C12A	121.17 (19)
C10—C11—C12	121.49 (19)	C10A—C11A—H11A	119.4
C10—C11—H11	119.3	C12A—C11A—H11A	119.4
C12—C11—H11	119.3	C11A—C12A—C17A	121.7 (2)
C11—C12—C17	122.1 (2)	C11A—C12A—C13A	118.89 (17)
C11—C12—C13	118.98 (19)	C17A—C12A—C13A	119.44 (19)
C17—C12—C13	119.0 (2)	C14A—C13A—C12A	117.06 (16)
C14—C13—C8	123.81 (17)	C14A—C13A—C8A	123.40 (17)
C14—C13—C12	117.12 (18)	C12A—C13A—C8A	119.53 (16)
C8—C13—C12	119.06 (18)	C15A—C14A—C13A	121.6 (2)
C15—C14—C13	121.8 (2)	C15A—C14A—H14A	119.2
C15—C14—H14	119.1	C13A—C14A—H14A	119.2
C13—C14—H14	119.1	C14A—C15A—C16A	120.4 (2)
C14—C15—C16	120.4 (3)	C14A—C15A—H15A	119.8
C14—C15—H15	119.8	C16A—C15A—H15A	119.8
C16—C15—H15	119.8	C17A—C16A—C15A	119.7 (2)
C17—C16—C15	120.1 (2)	C17A—C16A—H16A	120.2
C17—C16—H16	119.9	C15A—C16A—H16A	120.2
C15—C16—H16	119.9	C16A—C17A—C12A	121.8 (2)
C16—C17—C12	121.6 (2)	C16A—C17A—H17A	119.1
C16—C17—H17	119.2	C12A—C17A—H17A	119.1
C12—C17—H17	119.2	O3A—C18A—N1A	123.91 (16)
O3—C18—N1	124.33 (16)	O3A—C18A—N1A	123.91 (16)
O3—C18—N1	124.33 (16)	O3A—C18A—N1A	123.91 (16)
O3—C18—C19	119.64 (17)	O3A—C18A—C19A	119.49 (17)
O3—C18—C19	119.64 (17)	O3A—C18A—C19A	119.49 (17)
N1—C18—C19	116.02 (17)	O3A—C18A—C19A	119.49 (17)
C18—C19—H19A	109.5	N1A—C18A—C19A	116.59 (16)
C18—C19—H19B	109.5	C18A—C19A—H19D	109.5
H19A—C19—H19B	109.5	C18A—C19A—H19E	109.5
C18—C19—H19C	109.5	H19D—C19A—H19E	109.5
H19A—C19—H19C	109.5	C18A—C19A—H19F	109.5
H19B—C19—H19C	109.5	H19D—C19A—H19F	109.5
C1A—O1A—H1A1	109.5	H19E—C19A—H19F	109.5
O1—C1—C2—C3	177.50 (19)	C6A—C1A—C2A—C3A	−0.1 (3)
C6—C1—C2—C3	−1.1 (3)	C1A—C2A—C3A—C4A	−0.1 (4)
C1—C2—C3—C4	0.1 (3)	C2A—C3A—C4A—C5A	0.1 (4)
C2—C3—C4—C5	0.2 (4)	C3A—C4A—C5A—C6A	0.1 (4)
C3—C4—C5—C6	0.4 (4)	C4A—C5A—C6A—C1A	−0.3 (3)
C4—C5—C6—C1	−1.3 (3)	C4A—C5A—C6A—C7A	178.4 (2)
C4—C5—C6—C7	179.9 (2)	O1A—C1A—C6A—C5A	−178.92 (18)
O1—C1—C6—C5	−177.01 (17)	C2A—C1A—C6A—C5A	0.3 (3)
C2—C1—C6—C5	1.7 (3)	O1A—C1A—C6A—C7A	2.3 (2)
O1—C1—C6—C7	1.8 (2)	C2A—C1A—C6A—C7A	−178.44 (17)
C2—C1—C6—C7	−179.54 (17)	C18A—N1A—C7A—C8A	122.33 (17)
C18—N1—C7—C8	120.86 (18)	C18A—N1A—C7A—C6A	−110.10 (18)
C18—N1—C7—C6	−112.71 (19)	C5A—C6A—C7A—N1A	−114.0 (2)
C5—C6—C7—N1	−121.32 (19)	C1A—C6A—C7A—N1A	64.7 (2)
C1—C6—C7—N1	59.9 (2)	C5A—C6A—C7A—C8A	12.2 (2)
C5—C6—C7—C8	3.5 (2)	C1A—C6A—C7A—C8A	−169.11 (15)
C1—C6—C7—C8	−175.20 (15)	N1A—C7A—C8A—C9A	39.0 (2)
N1—C7—C8—C9	49.0 (2)	C6A—C7A—C8A—C9A	−85.9 (2)
C6—C7—C8—C9	−75.7 (2)	N1A—C7A—C8A—C13A	−143.40 (15)
N1—C7—C8—C13	−133.86 (17)	C6A—C7A—C8A—C13A	91.73 (19)
C6—C7—C8—C13	101.53 (19)	C13A—C8A—C9A—O2A	−174.72 (15)
C13—C8—C9—O2	−176.66 (17)	C7A—C8A—C9A—O2A	2.9 (3)
C7—C8—C9—O2	0.6 (3)	C13A—C8A—C9A—C10A	4.5 (3)
C13—C8—C9—C10	1.5 (3)	C7A—C8A—C9A—C10A	−177.87 (17)
C7—C8—C9—C10	178.75 (18)	O2A—C9A—C10A—C11A	176.72 (19)
O2—C9—C10—C11	176.8 (2)	C8A—C9A—C10A—C11A	−2.5 (3)
C8—C9—C10—C11	−1.3 (3)	C9A—C10A—C11A—C12A	−1.0 (3)
C9—C10—C11—C12	0.4 (3)	C10A—C11A—C12A—C17A	−176.2 (2)
C10—C11—C12—C17	179.9 (2)	C10A—C11A—C12A—C13A	2.3 (3)
C10—C11—C12—C13	0.2 (3)	C11A—C12A—C13A—C14A	−178.70 (18)
C9—C8—C13—C14	179.16 (18)	C17A—C12A—C13A—C14A	−0.2 (3)
C7—C8—C13—C14	2.0 (3)	C11A—C12A—C13A—C8A	−0.2 (3)
C9—C8—C13—C12	−0.8 (3)	C17A—C12A—C13A—C8A	178.39 (17)
C7—C8—C13—C12	−177.97 (17)	C9A—C8A—C13A—C14A	175.33 (17)
C11—C12—C13—C14	179.99 (19)	C7A—C8A—C13A—C14A	−2.4 (3)
C17—C12—C13—C14	0.3 (3)	C9A—C8A—C13A—C12A	−3.1 (2)
C11—C12—C13—C8	−0.1 (3)	C7A—C8A—C13A—C12A	179.18 (15)
C17—C12—C13—C8	−179.79 (19)	C12A—C13A—C14A—C15A	0.1 (3)
C8—C13—C14—C15	179.4 (2)	C8A—C13A—C14A—C15A	−178.39 (18)
C12—C13—C14—C15	−0.7 (3)	C13A—C14A—C15A—C16A	0.2 (3)
C13—C14—C15—C16	0.9 (4)	C14A—C15A—C16A—C17A	−0.4 (3)
C14—C15—C16—C17	−0.7 (4)	C15A—C16A—C17A—C12A	0.3 (4)
C15—C16—C17—C12	0.3 (4)	C11A—C12A—C17A—C16A	178.5 (2)
C11—C12—C17—C16	−179.8 (2)	C13A—C12A—C17A—C16A	−0.1 (3)
C13—C12—C17—C16	−0.1 (4)	C7A—N1A—C18A—O3A	−5.8 (3)
C7—N1—C18—O3	−2.7 (3)	C7A—N1A—C18A—O3A	−5.8 (3)
C7—N1—C18—O3	−2.7 (3)	C7A—N1A—C18A—O3A	−5.8 (3)
C7—N1—C18—C19	177.57 (19)	C7A—N1A—C18A—C19A	173.15 (18)
O1A—C1A—C2A—C3A	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	1.99	2.792 (2)	166
O2A—H2A1···O3ii	0.82	1.89	2.702 (2)	170
O2—H2···O3Aiii	0.82	1.81	2.588 (2)	159
O1A—H1A1···O3A	0.82	2.16	2.928 (2)	156
C7—H7···O3	0.98	2.51	2.901 (2)	104
C7A—H7A···O3A	0.98	2.47	2.879 (2)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.99	2.792 (2)	166
O2A—H2A1⋯O3ii	0.82	1.89	2.702 (2)	170
O2—H2⋯O3Aiii	0.82	1.81	2.588 (2)	159
O1A—H1A1⋯O3A	0.82	2.16	2.928 (2)	156

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