(E)-2-tert-Butyl-6-[(naphthalen-1-yl)imino-meth-yl]phenol.

The asymmetric unit of the title Schiff base compound, C(21)H(21)NO, contains two crystallographicaly independent mol-ecules. The dihedral angles between the naphthalene mean plane and the benzene ring are 29.28 (8) and 26.92.(8)° in the two mol-ecules. An intra-molecular O-H⋯N hydrogen bond and weak intra-molecular C-H⋯O hydrogen bonds stabilize the structure of each independent mol-ecule.

Related literature

For general background to the synthesis and catalytic activity of FI catalysts, see: Matsui & Fujita (2001 ▶); Matsui et al. (1999 ▶, 2001 ▶). For related structures, see: Hiller et al. (1993 ▶); Darensbourg et al. (2005 ▶); Jamjah et al. (2011 ▶).

Experimental

Crystal data

C21H21NO

M = 303.39

Orthorhombic,

a = 9.4770 (19) Å

b = 20.109 (4) Å

c = 34.595 (7) Å

V = 6593 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.5 × 0.4 × 0.3 mm

Data collection

Stoe IPDS II diffractometer

28480 measured reflections

8840 independent reflections

5781 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.155

S = 1.05

8840 reflections

424 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002395/bt5787sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002395/bt5787Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002395/bt5787Isup3.cml

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

C21H21NO	F(000) = 2592
Mr = 303.39	Dx = 1.223 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8840 reflections
a = 9.4770 (19) Å	θ = 2.5–29.2°
b = 20.109 (4) Å	µ = 0.07 mm−1
c = 34.595 (7) Å	T = 120 K
V = 6593 (2) Å3	Block, orange
Z = 16	0.5 × 0.4 × 0.3 mm

Stoe IPDS II diffractometer	5781 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
graphite	θmax = 29.2°, θmin = 2.5°
Detector resolution: 0.15 mm pixels mm-1	h = −10→12
rotation method scans	k = −27→23
28480 measured reflections	l = −39→47
8840 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0561P)2 + 2.5641P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
8840 reflections	Δρmax = 0.24 e Å−3
424 parameters	Δρmin = −0.23 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: 0.0039 (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	0.37905 (15)	0.43850 (7)	0.17017 (4)	0.0338 (3)
H1A	0.4051	0.4727	0.1810	0.051*
N1	0.39654 (18)	0.52936 (9)	0.22143 (5)	0.0332 (4)
C14	0.2144 (2)	0.34967 (10)	0.17797 (6)	0.0307 (4)
C13	0.2750 (2)	0.40972 (10)	0.19115 (6)	0.0300 (4)
C12	0.2293 (2)	0.44053 (10)	0.22547 (6)	0.0315 (4)
C9	0.5443 (2)	0.61773 (11)	0.17089 (6)	0.0366 (5)
H9	0.4867	0.5852	0.1601	0.044*
C15	0.1068 (2)	0.32295 (11)	0.20058 (6)	0.0334 (4)
H15	0.0642	0.2837	0.1925	0.040*
C1	0.4731 (2)	0.58316 (11)	0.23768 (6)	0.0345 (4)
C2	0.4857 (2)	0.59221 (11)	0.27685 (6)	0.0388 (5)
H2	0.4367	0.5644	0.2936	0.047*
C16	0.0602 (2)	0.35241 (11)	0.23474 (6)	0.0367 (5)
H16	−0.0118	0.3328	0.2490	0.044*
C17	0.1212 (2)	0.41069 (11)	0.24727 (6)	0.0367 (5)
H17	0.0910	0.4303	0.2702	0.044*
C5	0.6381 (2)	0.67555 (11)	0.22723 (7)	0.0364 (5)
C18	0.2653 (2)	0.31619 (10)	0.14061 (6)	0.0324 (4)
C11	0.2939 (2)	0.50132 (11)	0.23963 (6)	0.0349 (5)
H11	0.2604	0.5204	0.2623	0.042*
C10	0.5499 (2)	0.62500 (10)	0.21151 (6)	0.0336 (4)
C4	0.6460 (2)	0.68339 (12)	0.26778 (7)	0.0416 (5)
H4	0.7028	0.7166	0.2781	0.050*
C8	0.6230 (2)	0.65808 (12)	0.14724 (7)	0.0413 (5)
H8	0.6184	0.6524	0.1206	0.050*
C6	0.7170 (2)	0.71633 (12)	0.20179 (7)	0.0410 (5)
H6	0.7745	0.7495	0.2119	0.049*
C7	0.7101 (2)	0.70772 (12)	0.16279 (7)	0.0436 (5)
H7	0.7631	0.7347	0.1465	0.052*
C3	0.5715 (3)	0.64292 (12)	0.29195 (7)	0.0424 (5)
H3	0.5776	0.6489	0.3186	0.051*
O2	1.00404 (15)	0.13532 (7)	0.03168 (5)	0.0366 (3)
H2A	0.9468	0.1166	0.0457	0.055*
N2	0.89339 (17)	0.04113 (9)	0.07488 (5)	0.0322 (4)
C34	1.1074 (2)	0.09186 (10)	0.02161 (6)	0.0297 (4)
C22	0.7909 (2)	0.01274 (10)	0.10001 (6)	0.0303 (4)
C31	0.6520 (2)	0.04053 (10)	0.09993 (6)	0.0306 (4)
C35	1.2155 (2)	0.11257 (10)	−0.00385 (6)	0.0308 (4)
C33	1.1031 (2)	0.02646 (10)	0.03615 (6)	0.0296 (4)
C37	1.3157 (2)	0.00065 (11)	0.00143 (6)	0.0324 (4)
H37	1.3866	−0.0292	−0.0052	0.039*
C38	1.2083 (2)	−0.01867 (10)	0.02546 (6)	0.0313 (4)
H38	1.2053	−0.0621	0.0347	0.038*
C32	0.9909 (2)	0.00304 (11)	0.06118 (6)	0.0314 (4)
H32	0.9891	−0.0418	0.0677	0.038*
C29	0.4784 (2)	0.11944 (11)	0.07694 (6)	0.0370 (5)
H29	0.4551	0.1558	0.0616	0.044*
C39	1.2191 (2)	0.18265 (11)	−0.02143 (6)	0.0342 (4)
C23	0.8228 (2)	−0.03859 (11)	0.12478 (6)	0.0349 (4)
H23	0.9142	−0.0553	0.1254	0.042*
C26	0.5478 (2)	0.01151 (11)	0.12424 (6)	0.0329 (4)
C36	1.3179 (2)	0.06532 (11)	−0.01294 (6)	0.0323 (4)
H36	1.3911	0.0776	−0.0294	0.039*
C25	0.5844 (2)	−0.04207 (11)	0.14872 (6)	0.0375 (5)
H25	0.5161	−0.0611	0.1646	0.045*
C30	0.6139 (2)	0.09558 (10)	0.07665 (6)	0.0333 (4)
H30	0.6814	0.1157	0.0610	0.040*
C24	0.7194 (2)	−0.06625 (11)	0.14925 (6)	0.0377 (5)
H24	0.7429	−0.1010	0.1658	0.045*
C28	0.3743 (2)	0.08973 (11)	0.10011 (7)	0.0391 (5)
H28	0.2823	0.1058	0.0996	0.047*
C27	0.4082 (2)	0.03728 (11)	0.12329 (7)	0.0377 (5)
H27	0.3389	0.0181	0.1387	0.045*
C20	0.4227 (2)	0.29752 (11)	0.14468 (6)	0.0372 (5)
H20A	0.4357	0.2710	0.1675	0.056*
H20B	0.4782	0.3373	0.1467	0.056*
H20C	0.4521	0.2727	0.1224	0.056*
C19	0.1829 (3)	0.25239 (11)	0.13220 (7)	0.0413 (5)
H19A	0.1950	0.2217	0.1532	0.062*
H19B	0.2175	0.2327	0.1088	0.062*
H19C	0.0846	0.2627	0.1293	0.062*
C41	1.2218 (2)	0.23574 (11)	0.01050 (7)	0.0419 (5)
H41A	1.2248	0.2791	−0.0010	0.063*
H41B	1.3038	0.2294	0.0264	0.063*
H41C	1.1385	0.2318	0.0261	0.063*
C42	1.0883 (2)	0.19260 (12)	−0.04681 (7)	0.0426 (5)
H42A	1.0888	0.2368	−0.0573	0.064*
H42B	1.0048	0.1864	−0.0315	0.064*
H42C	1.0892	0.1608	−0.0675	0.064*
C40	1.3494 (3)	0.19301 (13)	−0.04700 (8)	0.0484 (6)
H40A	1.3469	0.1623	−0.0682	0.073*
H40B	1.4332	0.1856	−0.0320	0.073*
H40C	1.3498	0.2377	−0.0568	0.073*
C21	0.2438 (3)	0.36255 (11)	0.10589 (6)	0.0392 (5)
H21A	0.2753	0.3407	0.0828	0.059*
H21B	0.2972	0.4026	0.1097	0.059*
H21C	0.1455	0.3733	0.1035	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0327 (7)	0.0332 (8)	0.0354 (8)	−0.0053 (6)	0.0035 (6)	−0.0012 (6)
N1	0.0321 (9)	0.0290 (9)	0.0386 (9)	0.0032 (7)	−0.0038 (7)	−0.0008 (7)
C14	0.0268 (9)	0.0322 (11)	0.0331 (10)	0.0016 (8)	−0.0010 (8)	0.0044 (8)
C13	0.0265 (9)	0.0304 (10)	0.0331 (10)	0.0026 (8)	0.0003 (8)	0.0051 (8)
C12	0.0280 (9)	0.0320 (11)	0.0344 (10)	0.0052 (8)	−0.0004 (8)	−0.0003 (8)
C9	0.0374 (11)	0.0305 (11)	0.0418 (12)	0.0031 (9)	−0.0029 (9)	−0.0054 (9)
C15	0.0322 (10)	0.0300 (10)	0.0380 (11)	−0.0003 (8)	0.0009 (8)	0.0014 (9)
C1	0.0333 (10)	0.0282 (10)	0.0420 (11)	0.0056 (8)	−0.0053 (9)	−0.0050 (9)
C2	0.0436 (12)	0.0350 (12)	0.0378 (11)	0.0016 (9)	−0.0043 (9)	−0.0020 (9)
C16	0.0303 (10)	0.0393 (12)	0.0404 (11)	0.0023 (9)	0.0057 (8)	0.0055 (9)
C17	0.0340 (10)	0.0414 (12)	0.0347 (11)	0.0083 (9)	0.0031 (8)	0.0009 (9)
C5	0.0340 (10)	0.0317 (11)	0.0434 (12)	0.0047 (8)	−0.0053 (9)	−0.0046 (9)
C18	0.0360 (10)	0.0293 (10)	0.0319 (10)	0.0001 (8)	0.0022 (8)	0.0022 (8)
C11	0.0303 (10)	0.0371 (11)	0.0375 (11)	0.0078 (9)	−0.0035 (8)	−0.0029 (9)
C10	0.0305 (10)	0.0305 (11)	0.0400 (11)	0.0062 (8)	−0.0039 (8)	−0.0031 (9)
C4	0.0451 (12)	0.0344 (12)	0.0454 (12)	−0.0009 (10)	−0.0090 (10)	−0.0079 (10)
C8	0.0423 (12)	0.0395 (13)	0.0422 (12)	0.0029 (10)	0.0019 (9)	−0.0033 (10)
C6	0.0362 (11)	0.0361 (12)	0.0506 (13)	−0.0001 (9)	−0.0017 (10)	−0.0040 (10)
C7	0.0401 (12)	0.0386 (13)	0.0520 (14)	−0.0001 (10)	0.0053 (10)	0.0000 (10)
C3	0.0522 (14)	0.0362 (12)	0.0388 (12)	0.0016 (10)	−0.0096 (10)	−0.0056 (10)
O2	0.0313 (7)	0.0307 (8)	0.0478 (9)	0.0042 (6)	0.0070 (6)	0.0025 (7)
N2	0.0277 (8)	0.0356 (9)	0.0334 (9)	−0.0012 (7)	0.0006 (7)	0.0005 (7)
C34	0.0271 (9)	0.0293 (10)	0.0326 (10)	0.0018 (8)	−0.0023 (7)	−0.0032 (8)
C22	0.0288 (9)	0.0308 (11)	0.0314 (10)	−0.0019 (8)	−0.0005 (8)	−0.0003 (8)
C31	0.0316 (10)	0.0304 (10)	0.0299 (10)	−0.0024 (8)	−0.0011 (8)	−0.0017 (8)
C35	0.0263 (9)	0.0323 (11)	0.0340 (10)	−0.0020 (8)	−0.0031 (8)	−0.0005 (8)
C33	0.0269 (9)	0.0310 (10)	0.0308 (9)	−0.0006 (8)	−0.0030 (7)	−0.0015 (8)
C37	0.0297 (9)	0.0321 (10)	0.0355 (10)	0.0041 (8)	−0.0010 (8)	−0.0035 (8)
C38	0.0310 (10)	0.0290 (10)	0.0338 (10)	0.0022 (8)	−0.0038 (8)	0.0009 (8)
C32	0.0295 (9)	0.0313 (10)	0.0335 (10)	−0.0017 (8)	−0.0021 (8)	0.0008 (8)
C29	0.0377 (11)	0.0339 (11)	0.0393 (11)	0.0045 (9)	−0.0039 (9)	−0.0023 (9)
C39	0.0318 (10)	0.0316 (11)	0.0393 (11)	−0.0020 (8)	−0.0014 (8)	0.0025 (9)
C23	0.0330 (10)	0.0346 (11)	0.0371 (11)	0.0023 (8)	−0.0026 (8)	0.0013 (9)
C26	0.0306 (10)	0.0326 (11)	0.0356 (10)	−0.0049 (8)	0.0013 (8)	−0.0033 (8)
C36	0.0273 (9)	0.0369 (11)	0.0327 (10)	−0.0008 (8)	0.0007 (8)	−0.0020 (9)
C25	0.0395 (11)	0.0343 (11)	0.0388 (11)	−0.0047 (9)	0.0056 (9)	0.0040 (9)
C30	0.0339 (10)	0.0302 (11)	0.0357 (10)	−0.0010 (8)	−0.0010 (8)	0.0001 (8)
C24	0.0411 (11)	0.0361 (12)	0.0358 (11)	−0.0005 (9)	−0.0002 (9)	0.0063 (9)
C28	0.0313 (10)	0.0386 (12)	0.0476 (13)	0.0024 (9)	−0.0010 (9)	−0.0102 (10)
C27	0.0325 (10)	0.0385 (12)	0.0420 (12)	−0.0033 (9)	0.0046 (9)	−0.0041 (10)
C20	0.0399 (11)	0.0305 (11)	0.0413 (12)	0.0012 (9)	0.0095 (9)	0.0006 (9)
C19	0.0505 (13)	0.0324 (11)	0.0410 (12)	−0.0076 (10)	0.0032 (10)	−0.0023 (10)
C41	0.0432 (12)	0.0316 (12)	0.0508 (13)	−0.0033 (9)	−0.0066 (10)	0.0017 (10)
C42	0.0459 (12)	0.0361 (12)	0.0460 (13)	−0.0007 (10)	−0.0079 (10)	0.0076 (10)
C40	0.0454 (13)	0.0408 (14)	0.0592 (15)	−0.0052 (10)	0.0102 (11)	0.0109 (12)
C21	0.0492 (13)	0.0378 (12)	0.0306 (10)	0.0013 (10)	0.0008 (9)	0.0008 (9)

O1—C13	1.354 (2)	C31—C26	1.423 (3)
O1—H1A	0.8200	C35—C36	1.394 (3)
N1—C11	1.289 (3)	C35—C39	1.535 (3)
N1—C1	1.419 (3)	C33—C38	1.398 (3)
C14—C15	1.393 (3)	C33—C32	1.450 (3)
C14—C13	1.413 (3)	C37—C38	1.371 (3)
C14—C18	1.535 (3)	C37—C36	1.393 (3)
C13—C12	1.408 (3)	C37—H37	0.9300
C12—C17	1.406 (3)	C38—H38	0.9300
C12—C11	1.452 (3)	C32—H32	0.9300
C9—C8	1.372 (3)	C29—C30	1.371 (3)
C9—C10	1.414 (3)	C29—C28	1.405 (3)
C9—H9	0.9300	C29—H29	0.9300
C15—C16	1.394 (3)	C39—C42	1.532 (3)
C15—H15	0.9300	C39—C40	1.534 (3)
C1—C2	1.373 (3)	C39—C41	1.537 (3)
C1—C10	1.434 (3)	C23—C24	1.410 (3)
C2—C3	1.405 (3)	C23—H23	0.9300
C2—H2	0.9300	C26—C25	1.414 (3)
C16—C17	1.377 (3)	C26—C27	1.421 (3)
C16—H16	0.9300	C36—H36	0.9300
C17—H17	0.9300	C25—C24	1.369 (3)
C5—C4	1.414 (3)	C25—H25	0.9300
C5—C6	1.416 (3)	C30—H30	0.9300
C5—C10	1.424 (3)	C24—H24	0.9300
C18—C19	1.530 (3)	C28—C27	1.364 (3)
C18—C21	1.534 (3)	C28—H28	0.9300
C18—C20	1.545 (3)	C27—H27	0.9300
C11—H11	0.9300	C20—H20A	0.9600
C4—C3	1.364 (3)	C20—H20B	0.9600
C4—H4	0.9300	C20—H20C	0.9600
C8—C7	1.403 (3)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C6—C7	1.362 (3)	C19—H19C	0.9600
C6—H6	0.9300	C41—H41A	0.9600
C7—H7	0.9300	C41—H41B	0.9600
C3—H3	0.9300	C41—H41C	0.9600
O2—C34	1.358 (2)	C42—H42A	0.9600
O2—H2A	0.8200	C42—H42B	0.9600
N2—C32	1.290 (3)	C42—H42C	0.9600
N2—C22	1.423 (3)	C40—H40A	0.9600
C34—C33	1.409 (3)	C40—H40B	0.9600
C34—C35	1.414 (3)	C40—H40C	0.9600
C22—C23	1.375 (3)	C21—H21A	0.9600
C22—C31	1.430 (3)	C21—H21B	0.9600
C31—C30	1.416 (3)	C21—H21C	0.9600
C13—O1—H1A	109.5	C38—C37—H37	120.2
C11—N1—C1	121.75 (19)	C36—C37—H37	120.2
C15—C14—C13	116.50 (19)	C37—C38—C33	120.41 (19)
C15—C14—C18	122.24 (19)	C37—C38—H38	119.8
C13—C14—C18	121.26 (17)	C33—C38—H38	119.8
O1—C13—C12	119.22 (18)	N2—C32—C33	123.48 (19)
O1—C13—C14	119.22 (17)	N2—C32—H32	118.3
C12—C13—C14	121.56 (18)	C33—C32—H32	118.3
C17—C12—C13	119.24 (19)	C30—C29—C28	120.9 (2)
C17—C12—C11	119.04 (19)	C30—C29—H29	119.6
C13—C12—C11	121.69 (19)	C28—C29—H29	119.6
C8—C9—C10	120.7 (2)	C42—C39—C40	107.66 (19)
C8—C9—H9	119.6	C42—C39—C35	109.20 (17)
C10—C9—H9	119.6	C40—C39—C35	111.78 (18)
C14—C15—C16	123.0 (2)	C42—C39—C41	109.58 (18)
C14—C15—H15	118.5	C40—C39—C41	107.86 (19)
C16—C15—H15	118.5	C35—C39—C41	110.68 (17)
C2—C1—N1	122.5 (2)	C22—C23—C24	121.2 (2)
C2—C1—C10	120.1 (2)	C22—C23—H23	119.4
N1—C1—C10	117.18 (19)	C24—C23—H23	119.4
C1—C2—C3	120.9 (2)	C25—C26—C27	121.36 (19)
C1—C2—H2	119.5	C25—C26—C31	119.75 (19)
C3—C2—H2	119.5	C27—C26—C31	118.9 (2)
C17—C16—C15	119.7 (2)	C37—C36—C35	123.04 (19)
C17—C16—H16	120.1	C37—C36—H36	118.5
C15—C16—H16	120.1	C35—C36—H36	118.5
C16—C17—C12	120.0 (2)	C24—C25—C26	120.6 (2)
C16—C17—H17	120.0	C24—C25—H25	119.7
C12—C17—H17	120.0	C26—C25—H25	119.7
C4—C5—C6	121.6 (2)	C29—C30—C31	120.6 (2)
C4—C5—C10	119.3 (2)	C29—C30—H30	119.7
C6—C5—C10	119.1 (2)	C31—C30—H30	119.7
C19—C18—C21	107.05 (18)	C25—C24—C23	120.1 (2)
C19—C18—C14	111.58 (17)	C25—C24—H24	119.9
C21—C18—C14	110.56 (17)	C23—C24—H24	119.9
C19—C18—C20	107.82 (18)	C27—C28—C29	119.9 (2)
C21—C18—C20	110.30 (17)	C27—C28—H28	120.0
C14—C18—C20	109.47 (17)	C29—C28—H28	120.0
N1—C11—C12	121.45 (19)	C28—C27—C26	121.0 (2)
N1—C11—H11	119.3	C28—C27—H27	119.5
C12—C11—H11	119.3	C26—C27—H27	119.5
C9—C10—C5	118.4 (2)	C18—C20—H20A	109.5
C9—C10—C1	123.20 (19)	C18—C20—H20B	109.5
C5—C10—C1	118.4 (2)	H20A—C20—H20B	109.5
C3—C4—C5	121.0 (2)	C18—C20—H20C	109.5
C3—C4—H4	119.5	H20A—C20—H20C	109.5
C5—C4—H4	119.5	H20B—C20—H20C	109.5
C9—C8—C7	120.8 (2)	C18—C19—H19A	109.5
C9—C8—H8	119.6	C18—C19—H19B	109.5
C7—C8—H8	119.6	H19A—C19—H19B	109.5
C7—C6—C5	121.1 (2)	C18—C19—H19C	109.5
C7—C6—H6	119.4	H19A—C19—H19C	109.5
C5—C6—H6	119.4	H19B—C19—H19C	109.5
C6—C7—C8	119.9 (2)	C39—C41—H41A	109.5
C6—C7—H7	120.0	C39—C41—H41B	109.5
C8—C7—H7	120.0	H41A—C41—H41B	109.5
C4—C3—C2	120.3 (2)	C39—C41—H41C	109.5
C4—C3—H3	119.8	H41A—C41—H41C	109.5
C2—C3—H3	119.8	H41B—C41—H41C	109.5
C34—O2—H2A	109.5	C39—C42—H42A	109.5
C32—N2—C22	118.35 (18)	C39—C42—H42B	109.5
O2—C34—C33	119.24 (18)	H42A—C42—H42B	109.5
O2—C34—C35	119.52 (18)	C39—C42—H42C	109.5
C33—C34—C35	121.23 (18)	H42A—C42—H42C	109.5
C23—C22—N2	122.13 (18)	H42B—C42—H42C	109.5
C23—C22—C31	119.79 (18)	C39—C40—H40A	109.5
N2—C22—C31	118.05 (18)	C39—C40—H40B	109.5
C30—C31—C26	118.67 (19)	H40A—C40—H40B	109.5
C30—C31—C22	122.78 (18)	C39—C40—H40C	109.5
C26—C31—C22	118.55 (19)	H40A—C40—H40C	109.5
C36—C35—C34	116.39 (19)	H40B—C40—H40C	109.5
C36—C35—C39	121.37 (18)	C18—C21—H21A	109.5
C34—C35—C39	122.23 (18)	C18—C21—H21B	109.5
C38—C33—C34	119.41 (18)	H21A—C21—H21B	109.5
C38—C33—C32	118.03 (19)	C18—C21—H21C	109.5
C34—C33—C32	122.54 (18)	H21A—C21—H21C	109.5
C38—C37—C36	119.51 (19)	H21B—C21—H21C	109.5
C15—C14—C13—O1	−179.31 (18)	C32—N2—C22—C23	32.8 (3)
C18—C14—C13—O1	0.6 (3)	C32—N2—C22—C31	−149.19 (19)
C15—C14—C13—C12	0.4 (3)	C23—C22—C31—C30	176.7 (2)
C18—C14—C13—C12	−179.71 (18)	N2—C22—C31—C30	−1.4 (3)
O1—C13—C12—C17	179.99 (18)	C23—C22—C31—C26	−3.4 (3)
C14—C13—C12—C17	0.3 (3)	N2—C22—C31—C26	178.49 (17)
O1—C13—C12—C11	−2.0 (3)	O2—C34—C35—C36	−179.94 (18)
C14—C13—C12—C11	178.36 (18)	C33—C34—C35—C36	−1.3 (3)
C13—C14—C15—C16	−0.6 (3)	O2—C34—C35—C39	−1.3 (3)
C18—C14—C15—C16	179.44 (19)	C33—C34—C35—C39	177.37 (18)
C11—N1—C1—C2	26.7 (3)	O2—C34—C33—C38	179.19 (18)
C11—N1—C1—C10	−159.32 (19)	C35—C34—C33—C38	0.5 (3)
N1—C1—C2—C3	174.9 (2)	O2—C34—C33—C32	0.9 (3)
C10—C1—C2—C3	1.1 (3)	C35—C34—C33—C32	−177.72 (18)
C14—C15—C16—C17	0.2 (3)	C36—C37—C38—C33	−1.3 (3)
C15—C16—C17—C12	0.5 (3)	C34—C33—C38—C37	0.8 (3)
C13—C12—C17—C16	−0.8 (3)	C32—C33—C38—C37	179.13 (19)
C11—C12—C17—C16	−178.86 (19)	C22—N2—C32—C33	−178.36 (18)
C15—C14—C18—C19	0.5 (3)	C38—C33—C32—N2	175.45 (19)
C13—C14—C18—C19	−179.45 (18)	C34—C33—C32—N2	−6.3 (3)
C15—C14—C18—C21	119.5 (2)	C36—C35—C39—C42	115.9 (2)
C13—C14—C18—C21	−60.4 (2)	C34—C35—C39—C42	−62.7 (3)
C15—C14—C18—C20	−118.8 (2)	C36—C35—C39—C40	−3.1 (3)
C13—C14—C18—C20	61.3 (2)	C34—C35—C39—C40	178.25 (19)
C1—N1—C11—C12	−171.02 (18)	C36—C35—C39—C41	−123.4 (2)
C17—C12—C11—N1	177.58 (19)	C34—C35—C39—C41	58.0 (2)
C13—C12—C11—N1	−0.5 (3)	N2—C22—C23—C24	−179.59 (19)
C8—C9—C10—C5	0.5 (3)	C31—C22—C23—C24	2.4 (3)
C8—C9—C10—C1	−178.3 (2)	C30—C31—C26—C25	−177.89 (19)
C4—C5—C10—C9	−179.6 (2)	C22—C31—C26—C25	2.2 (3)
C6—C5—C10—C9	−0.2 (3)	C30—C31—C26—C27	2.2 (3)
C4—C5—C10—C1	−0.7 (3)	C22—C31—C26—C27	−177.73 (19)
C6—C5—C10—C1	178.65 (19)	C38—C37—C36—C35	0.5 (3)
C2—C1—C10—C9	178.7 (2)	C34—C35—C36—C37	0.8 (3)
N1—C1—C10—C9	4.6 (3)	C39—C35—C36—C37	−177.88 (19)
C2—C1—C10—C5	−0.1 (3)	C27—C26—C25—C24	180.0 (2)
N1—C1—C10—C5	−174.25 (18)	C31—C26—C25—C24	0.1 (3)
C6—C5—C4—C3	−178.7 (2)	C28—C29—C30—C31	−0.3 (3)
C10—C5—C4—C3	0.6 (3)	C26—C31—C30—C29	−1.4 (3)
C10—C9—C8—C7	−0.4 (3)	C22—C31—C30—C29	178.5 (2)
C4—C5—C6—C7	179.1 (2)	C26—C25—C24—C23	−1.2 (3)
C10—C5—C6—C7	−0.3 (3)	C22—C23—C24—C25	−0.1 (3)
C5—C6—C7—C8	0.4 (4)	C30—C29—C28—C27	1.3 (3)
C9—C8—C7—C6	−0.1 (4)	C29—C28—C27—C26	−0.5 (3)
C5—C4—C3—C2	0.3 (4)	C25—C26—C27—C28	178.8 (2)
C1—C2—C3—C4	−1.2 (4)	C31—C26—C27—C28	−1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.81	2.552 (2)	150.
O2—H2A···N2	0.82	1.89	2.631 (2)	150.
C20—H20B···O1	0.96	2.38	2.998 (3)	121.
C21—H21B···O1	0.96	2.35	2.987 (3)	124.
C41—H41C···O2	0.96	2.33	2.979 (3)	124.
C42—H42B···O2	0.96	2.41	3.056 (3)	124.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.81	2.552 (2)	150
O2—H2A⋯N2	0.82	1.89	2.631 (2)	150
C20—H20B⋯O1	0.96	2.38	2.998 (3)	121
C21—H21B⋯O1	0.96	2.35	2.987 (3)	124
C41—H41C⋯O2	0.96	2.33	2.979 (3)	124
C42—H42B⋯O2	0.96	2.41	3.056 (3)	124