2,4,4-Tri­methyl-2-phenyl-3-pentanone oxime

The title compound, C₁₄H₂₁NO, has two mol­ecules in the asymmetric unit. Each mol­ecule forms hydrogen-bonded dimers about inversion centers via O—H...N hydrogen bonds between oxime groups. The N—O distances in the oxime groups are 1.4160 (15) and 1.4131 (14) Å.

S1. Comment

We had previously carried out spectral and kinetic measurements on a series of persistent iminoxyl radicals (Eisenhauer, Wang, Brown et al., 1997). This study of the title compound, (I), was conducted in order to unequivocally establish the geometry about the C=N—O group, and to see if there would be any angular distortions induced by the bulky groups (i.e., ^tBu and cumenyl) surrounding the oxime group. The angle in question in both molecules, C2—C3—C4 at 123.39 (11) and C12—C13—C14 at 123.85 (11)° is similar, and, not very much larger than that expected for an sp² hybridized C atom. Therefore we conclude that neither molecule exhibits large distortions. \sch

The two molecules constituting the asymmetric unit contain similar bond distances and angles as is partly evident in Table 1. In both of these molecules, the oxime –C(=NOH)- group is staggered with respect to two of the methyl groups at the ^tBu end of the molecule with the H atom on each O atom pointing away from this ^tBu group and almost eclipsed with respect to one of the methyl groups on the other end. Additionally, in both molecules the oxime OH is located anti to the larger cumenyl group as expected from steric considerations. The two conformers also contain short intramolecular H to H contacts, namely H1B to H5C and H11B to H15C of 1.97 (3) and 2.07 (3) Å, respectively. These H atoms are located on different methyl groups, and this distance is noteworthy as nonbonding H···H contacts are normally about twice the van der Waals radius of H or 2.4 Å (Jeffrey & Saenger, 1991).

The crystal packing is assisted by hydrogen bonding (Table 2). These are conventional, almost-linear, hydrogen bonds from the H atom on the OH groups to the lone pair on the N atoms in the inversion-related molecule. This is a pattern usually observed in other oxime crystal structures (Hamilton, 1961; Bertolasi et al., 1982).

S2. Experimental

The title compound was prepared as reported previously (Eisenhauer, Wang, Labaziewicz et al., 1997). Crystals melting at 455–457 K were obtained by allowing the slow concentration of a benzene solution of (I) in a volumetric flask over a period of five years.

S3. Refinement

The C—H distances and U_iso values for the refined H atoms are in the ranges 0.94 (2)–1.04 (2) Å and 0.058 (5)–0.106 (7) Ų, respectively.

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1998).

Figures

Fig. 1. View of (I) with 50% probability displacement ellipsoids.

(I)

Crystal data

C14H21NO	Z = 4
Mr = 219.32	F(000) = 480
Triclinic, P1	Dx = 1.118 Mg m^−3
a = 6.2605 (7) Å	Mo Kα radiation, λ = 0.71069 Å
b = 12.0422 (8) Å	Cell parameters from 25 reflections
c = 18.193 (2) Å	θ = 14–16°
α = 105.689 (7)°	µ = 0.07 mm^−1
β = 95.477 (9)°	T = 293 K
γ = 95.672 (7)°	Block, white
V = 1303.3 (2) Å^3	0.40 × 0.40 × 0.25 mm

Data collection

Enraf Nonius TurboCAD4 diffractometer	Rint = 0.010
non–profiled ω/2θ scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: ψ scan (North et al., 1968)	h = 0→7
Tmin = 0.95, Tmax = 0.98	k = −14→14
5052 measured reflections	l = −21→21
4591 independent reflections	3 standard reflections every 250 min
3606 reflections with I > 2σ(I)	intensity decay: 5%

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0513*P)^2 + 0.24*P], where P = (Max(Fo^2,0) + 2*Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.038	(Δ/σ)max = 0.001
wR(F^2) = 0.105	Δρmax = 0.18 e Å^−3
S = 1.01	Δρmin = −0.13 e Å^−3
4591 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
458 parameters	Extinction coefficient: 0.037 (3)
0 restraints

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. Positions of non H-atoms were located using SIR97 (Altomare et al., 1999) and this model was refined with first isotropic and then anisotropic displacement parameters to convergence. A difference Fourier map indicated the possible locations of the H atoms. They were treated as such and refined freely without constraint resulting in the final figures of merit for (I).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O31	0.87093 (19)	0.38234 (10)	0.43891 (6)	0.0585 (3)
H31	0.967 (4)	0.447 (2)	0.4428 (12)	0.092 (7)*
N31	0.83736 (19)	0.40584 (10)	0.51722 (7)	0.0456 (3)
C1	0.4372 (3)	0.41019 (17)	0.62418 (13)	0.0650 (5)
C2	0.6616 (2)	0.36959 (11)	0.61848 (8)	0.0440 (3)
C3	0.6973 (2)	0.33350 (11)	0.53294 (8)	0.0395 (3)
C4	0.5679 (2)	0.22573 (12)	0.47252 (8)	0.0459 (3)
C5	0.4133 (3)	0.14875 (16)	0.50493 (11)	0.0609 (5)
C21	0.6964 (2)	0.27119 (12)	0.65534 (8)	0.0454 (3)
C22	0.8756 (3)	0.21345 (14)	0.64293 (10)	0.0569 (4)
C23	0.9166 (4)	0.12708 (17)	0.67822 (13)	0.0769 (6)
C24	0.7773 (5)	0.09928 (19)	0.72701 (12)	0.0865 (7)
C25	0.6024 (5)	0.15638 (18)	0.74032 (11)	0.0802 (6)
C26	0.5607 (3)	0.24163 (15)	0.70519 (9)	0.0614 (5)
C27	0.8265 (3)	0.47414 (14)	0.66567 (10)	0.0584 (4)
C41	0.7245 (4)	0.14635 (16)	0.43224 (12)	0.0638 (5)
C42	0.4284 (3)	0.26740 (19)	0.41349 (12)	0.0664 (5)
O131	0.01307 (18)	0.97806 (9)	0.90944 (6)	0.0521 (3)
H131	−0.039 (3)	1.0283 (18)	0.9499 (12)	0.079 (6)*
N131	0.10928 (18)	0.90572 (9)	0.94891 (6)	0.0402 (3)
C11	0.5656 (3)	0.79593 (16)	0.96739 (13)	0.0617 (5)
C12	0.3201 (2)	0.75863 (11)	0.95873 (8)	0.0414 (3)
C13	0.2068 (2)	0.82671 (11)	0.90901 (7)	0.0364 (3)
C14	0.2232 (2)	0.80708 (12)	0.82209 (8)	0.0460 (4)
C15	0.3311 (4)	0.70046 (16)	0.78390 (11)	0.0609 (5)
C121	0.2533 (2)	0.62722 (11)	0.92467 (8)	0.0406 (3)
C122	0.3989 (3)	0.54693 (14)	0.91621 (10)	0.0555 (4)
C123	0.3290 (3)	0.42889 (15)	0.88556 (11)	0.0650 (5)
C124	0.1138 (3)	0.38901 (15)	0.86424 (11)	0.0639 (5)
C125	−0.0334 (3)	0.46716 (15)	0.87349 (11)	0.0623 (4)
C126	0.0352 (2)	0.58509 (13)	0.90399 (10)	0.0510 (4)
C127	0.2545 (3)	0.78915 (16)	1.04064 (9)	0.0551 (4)
C141	0.3590 (4)	0.91561 (17)	0.81311 (12)	0.0706 (6)
C142	−0.0033 (3)	0.78868 (17)	0.77710 (10)	0.0614 (5)
H1A	0.418 (3)	0.4441 (19)	0.6788 (13)	0.088 (6)*
H1B	0.320 (3)	0.3462 (19)	0.6039 (12)	0.086 (6)*
H1C	0.421 (3)	0.470 (2)	0.5970 (13)	0.097 (7)*
H5A	0.340 (3)	0.0847 (16)	0.4617 (11)	0.068 (5)*
H5B	0.494 (3)	0.1151 (17)	0.5426 (11)	0.078 (6)*
H5C	0.301 (4)	0.1917 (19)	0.5295 (13)	0.093 (7)*
H11A	0.595 (3)	0.8802 (19)	0.9909 (11)	0.081 (6)*
H11B	0.625 (3)	0.7758 (16)	0.9188 (11)	0.068 (5)*
H11C	0.649 (3)	0.7597 (17)	1.0029 (11)	0.076 (6)*
H12A	0.307 (3)	0.8735 (17)	1.0685 (10)	0.065 (5)*
H12B	0.092 (3)	0.7733 (16)	1.0400 (10)	0.070 (5)*
H12C	0.316 (3)	0.7398 (16)	1.0682 (10)	0.066 (5)*
H14A	−0.091 (3)	0.7218 (18)	0.7858 (11)	0.079 (6)*
H14B	−0.083 (3)	0.859 (2)	0.7937 (12)	0.090 (6)*
H14C	0.005 (3)	0.7715 (17)	0.7227 (12)	0.080 (6)*
H14D	0.290 (3)	0.9906 (17)	0.8346 (10)	0.071 (5)*
H14E	0.372 (3)	0.9070 (18)	0.7603 (13)	0.094 (7)*
H14F	0.513 (4)	0.924 (2)	0.8400 (14)	0.102 (8)*
H15A	0.335 (3)	0.6996 (16)	0.7303 (11)	0.072 (5)*
H15B	0.243 (3)	0.6263 (18)	0.7841 (10)	0.075 (5)*
H15C	0.475 (3)	0.7033 (16)	0.8073 (11)	0.070 (6)*
H22	0.970 (3)	0.2318 (14)	0.6078 (10)	0.058 (5)*
H23	1.037 (4)	0.090 (2)	0.6649 (13)	0.100 (8)*
H24	0.809 (4)	0.040 (2)	0.7494 (13)	0.106 (7)*
H25	0.502 (4)	0.135 (2)	0.7757 (13)	0.102 (7)*
H26	0.433 (3)	0.2815 (17)	0.7154 (11)	0.079 (6)*
H27A	0.800 (3)	0.4923 (15)	0.7204 (11)	0.065 (5)*
H27B	0.804 (3)	0.5421 (15)	0.6477 (9)	0.060 (5)*
H27C	0.984 (3)	0.4571 (17)	0.6613 (11)	0.078 (6)*
H41A	0.812 (3)	0.1151 (17)	0.4694 (12)	0.085 (6)*
H41B	0.824 (3)	0.1840 (18)	0.4059 (12)	0.084 (6)*
H41C	0.642 (3)	0.0792 (19)	0.3921 (12)	0.087 (6)*
H42A	0.342 (3)	0.1997 (19)	0.3740 (12)	0.089 (6)*
H42B	0.518 (3)	0.3133 (17)	0.3875 (11)	0.075 (5)*
H42C	0.322 (4)	0.3156 (19)	0.4406 (12)	0.089 (7)*
H112	0.548 (3)	0.5721 (16)	0.9317 (11)	0.076 (6)*
H123	0.436 (3)	0.3753 (18)	0.8788 (11)	0.083 (6)*
H124	0.066 (3)	0.3077 (17)	0.8420 (11)	0.074 (5)*
H125	−0.184 (3)	0.4435 (17)	0.8580 (11)	0.079 (6)*
H126	−0.066 (3)	0.6386 (15)	0.9094 (9)	0.059 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O31	0.0697 (7)	0.0575 (7)	0.0496 (6)	−0.0105 (6)	0.0165 (5)	0.0209 (5)
N31	0.0511 (7)	0.0420 (6)	0.0465 (7)	−0.0023 (5)	0.0110 (5)	0.0182 (5)
C1	0.0660 (12)	0.0511 (10)	0.0826 (13)	0.0144 (9)	0.0281 (10)	0.0182 (10)
C2	0.0506 (8)	0.0339 (7)	0.0475 (8)	−0.0004 (6)	0.0131 (6)	0.0116 (6)
C3	0.0412 (7)	0.0336 (7)	0.0466 (8)	0.0016 (6)	0.0074 (6)	0.0170 (6)
C4	0.0511 (8)	0.0399 (7)	0.0456 (8)	−0.0040 (6)	0.0046 (6)	0.0141 (6)
C5	0.0678 (12)	0.0476 (9)	0.0594 (10)	−0.0194 (9)	0.0056 (9)	0.0124 (8)
C21	0.0567 (9)	0.0366 (7)	0.0397 (7)	−0.0076 (6)	0.0049 (6)	0.0104 (6)
C22	0.0597 (10)	0.0499 (9)	0.0617 (10)	0.0000 (8)	0.0018 (8)	0.0210 (8)
C23	0.0876 (15)	0.0558 (11)	0.0841 (14)	0.0071 (10)	−0.0143 (12)	0.0236 (10)
C24	0.132 (2)	0.0537 (11)	0.0723 (13)	−0.0171 (13)	−0.0173 (13)	0.0354 (10)
C25	0.1172 (18)	0.0638 (12)	0.0584 (11)	−0.0221 (13)	0.0085 (11)	0.0283 (10)
C26	0.0816 (13)	0.0510 (9)	0.0496 (9)	−0.0116 (9)	0.0159 (9)	0.0154 (7)
C27	0.0819 (13)	0.0394 (9)	0.0497 (9)	−0.0085 (8)	0.0105 (9)	0.0102 (7)
C41	0.0788 (12)	0.0467 (9)	0.0606 (11)	0.0021 (9)	0.0142 (10)	0.0063 (8)
C42	0.0660 (12)	0.0684 (12)	0.0639 (11)	−0.0062 (10)	−0.0079 (10)	0.0281 (10)
O131	0.0705 (7)	0.0431 (6)	0.0473 (6)	0.0217 (5)	0.0108 (5)	0.0144 (5)
N131	0.0459 (7)	0.0342 (6)	0.0415 (6)	0.0084 (5)	0.0070 (5)	0.0107 (5)
C11	0.0421 (9)	0.0481 (10)	0.0839 (13)	0.0011 (7)	−0.0034 (9)	0.0059 (9)
C12	0.0392 (7)	0.0360 (7)	0.0461 (8)	0.0063 (6)	0.0040 (6)	0.0067 (6)
C13	0.0349 (7)	0.0296 (6)	0.0410 (7)	−0.0018 (5)	0.0074 (5)	0.0050 (5)
C14	0.0582 (9)	0.0368 (7)	0.0418 (7)	0.0006 (6)	0.0156 (7)	0.0078 (6)
C15	0.0744 (13)	0.0561 (10)	0.0512 (10)	0.0124 (9)	0.0269 (9)	0.0057 (8)
C121	0.0433 (8)	0.0362 (7)	0.0435 (7)	0.0063 (6)	0.0085 (6)	0.0118 (6)
C122	0.0486 (9)	0.0449 (8)	0.0706 (11)	0.0113 (7)	0.0047 (8)	0.0116 (8)
C123	0.0730 (12)	0.0419 (9)	0.0811 (12)	0.0196 (9)	0.0132 (10)	0.0135 (8)
C124	0.0827 (13)	0.0360 (8)	0.0693 (11)	−0.0013 (8)	0.0144 (9)	0.0102 (8)
C125	0.0558 (10)	0.0497 (9)	0.0780 (12)	−0.0074 (8)	0.0081 (9)	0.0174 (8)
C126	0.0436 (8)	0.0429 (8)	0.0680 (10)	0.0053 (7)	0.0106 (7)	0.0169 (7)
C127	0.0744 (12)	0.0492 (9)	0.0429 (8)	0.0197 (9)	0.0018 (8)	0.0126 (7)
C141	0.0987 (16)	0.0520 (10)	0.0619 (11)	−0.0081 (10)	0.0357 (11)	0.0150 (9)
C142	0.0772 (12)	0.0552 (10)	0.0443 (9)	0.0080 (9)	−0.0016 (8)	0.0051 (8)

Geometric parameters (Å, º)

O31—N31	1.4160 (15)	C5—H5B	1.01 (2)
N31—C3	1.2811 (17)	C5—H5C	0.98 (2)
C1—C2	1.536 (2)	C22—H22	0.96 (2)
C2—C21	1.5343 (19)	C23—H23	0.94 (2)
C2—C27	1.542 (2)	C24—H24	0.94 (2)
C2—C3	1.5428 (19)	C25—H25	1.00 (2)
C3—C4	1.5490 (19)	C26—H26	0.98 (2)
C4—C41	1.535 (2)	C27—H27A	1.00 (2)
C4—C42	1.538 (2)	C27—H27B	0.98 (2)
C4—C5	1.540 (2)	C27—H27C	1.03 (2)
C21—C22	1.382 (2)	C41—H41A	1.00 (2)
C21—C26	1.390 (2)	C41—H41B	0.97 (2)
C22—C23	1.394 (2)	C41—H41C	0.99 (2)
C23—C24	1.382 (3)	C42—H42A	1.00 (2)
C24—C25	1.356 (3)	C42—H42B	0.99 (2)
C25—C26	1.381 (3)	C42—H42C	1.01 (2)
O131—N131	1.4131 (14)	O131—H131	0.93 (2)
N131—C13	1.2770 (17)	C11—H11A	0.98 (2)
C11—C12	1.538 (2)	C11—H11B	0.97 (2)
C12—C121	1.5338 (18)	C11—H11C	1.01 (2)
C12—C127	1.541 (2)	C15—H15A	0.97 (2)
C12—C13	1.5451 (19)	C15—H15B	1.00 (2)
C13—C14	1.5494 (18)	C15—H15C	0.95 (2)
C14—C141	1.543 (2)	C122—H112	0.94 (2)
C14—C142	1.532 (2)	C123—H123	0.97 (2)
C14—C15	1.538 (2)	C124—H124	0.96 (2)
C121—C122	1.382 (2)	C125—H125	0.95 (2)
C121—C126	1.387 (2)	C126—H126	0.94 (2)
C122—C123	1.387 (2)	C127—H12A	1.01 (2)
C123—C124	1.367 (3)	C127—H12B	1.02 (2)
C124—C125	1.371 (3)	C127—H12C	0.96 (2)
C125—C126	1.385 (2)	C141—H14D	1.04 (2)
O31—H31	0.92 (2)	C141—H14E	0.95 (2)
C1—H1A	0.99 (2)	C141—H14F	1.02 (2)
C1—H1B	0.98 (2)	C142—H14A	0.99 (2)
C1—H1C	0.99 (2)	C142—H14B	1.01 (2)
C5—H5A	0.98 (2)	C142—H14C	0.96 (2)
C3—N31—O31	115.83 (11)	C23—C22—H22	120 (1)
C21—C2—C1	114.01 (13)	C22—C23—H23	116 (1)
C21—C2—C27	105.55 (12)	C24—C23—H23	125 (1)
C1—C2—C27	106.31 (14)	C23—C24—H24	117 (1)
C21—C2—C3	110.94 (11)	C25—C24—H24	123 (1)
C1—C2—C3	108.51 (13)	C24—C25—H25	119 (1)
C27—C2—C3	111.45 (11)	C26—C25—H25	120 (1)
N31—C3—C2	112.31 (12)	C21—C26—H26	120 (1)
N31—C3—C4	124.21 (12)	C25—C26—H26	119 (1)
C2—C3—C4	123.39 (11)	H27A—C27—H27B	108 (1)
C41—C4—C42	110.29 (15)	H27A—C27—H27C	110 (1)
C41—C4—C5	105.98 (14)	H27B—C27—H27C	109 (1)
C42—C4—C5	106.78 (14)	C4—C41—H41A	112 (1)
C41—C4—C3	109.83 (13)	C4—C41—H41B	114 (1)
C42—C4—C3	108.66 (13)	C4—C41—H41C	110 (1)
C5—C4—C3	115.20 (12)	H41A—C41—H41B	108 (2)
C22—C21—C26	117.78 (15)	H41A—C41—H41C	108 (2)
C22—C21—C2	119.68 (13)	H41B—C41—H41C	106 (2)
C26—C21—C2	122.42 (15)	C4—C42—H42A	110 (1)
C21—C22—C23	121.05 (18)	C4—C42—H42B	112 (1)
C24—C23—C22	119.6 (2)	C4—C42—H42C	109 (1)
C25—C24—C23	119.82 (19)	H42A—C42—H42B	109 (2)
C24—C25—C26	120.7 (2)	H42A—C42—H42C	107 (2)
C25—C26—C21	121.0 (2)	H42B—C42—H42C	110 (2)
C13—N131—O131	116.25 (11)	C12—C11—H11A	109 (1)
C121—C12—C11	113.81 (12)	C12—C11—H11B	113 (1)
C121—C12—C127	105.91 (12)	C12—C11—H11C	112 (1)
C11—C12—C127	106.62 (14)	H11A—C11—H11B	109 (2)
C121—C12—C13	110.88 (11)	H11A—C11—H11C	106 (2)
C11—C12—C13	108.11 (13)	H11B—C11—H11C	107 (2)
C127—C12—C13	111.46 (11)	C14—C15—H15A	107 (1)
N131—C13—C12	112.05 (11)	C14—C15—H15B	111 (1)
N131—C13—C14	123.97 (12)	C14—C15—H15C	113 (1)
C12—C13—C14	123.85 (11)	H15A—C15—H15B	107 (1)
C142—C14—C141	110.70 (16)	H15A—C15—H15C	109 (2)
C15—C14—C141	107.52 (14)	H15B—C15—H15C	110 (2)
C142—C14—C15	105.67 (14)	C121—C122—H112	120 (1)
C141—C14—C13	107.58 (12)	C123—C122—H112	119 (1)
C142—C14—C13	110.13 (12)	C122—C123—H123	119 (1)
C15—C14—C13	115.22 (13)	C124—C123—H123	121 (1)
C122—C121—C126	117.57 (14)	C123—C124—H124	121 (1)
C122—C121—C12	123.39 (13)	C125—C124—H124	120 (1)
C126—C121—C12	118.98 (12)	C124—C125—H125	122 (1)
C121—C122—C123	120.91 (16)	C126—C125—H125	118 (1)
C124—C123—C122	120.73 (16)	C121—C126—H126	119 (1)
C123—C124—C125	119.20 (16)	C125—C126—H126	120 (1)
C124—C125—C126	120.36 (17)	H12A—C127—H12B	110 (1)
C125—C126—C121	121.19 (15)	H12A—C127—H12C	110 (1)
C2—C1—H1A	110 (1)	H12B—C127—H12C	106 (1)
C2—C1—H1B	113 (1)	H14D—C141—H14E	109 (2)
C2—C1—H1C	111 (1)	H14D—C141—H14F	110 (2)
H1A—C1—H1B	106 (2)	H14E—C141—H14F	106 (2)
H1A—C1—H1C	108 (2)	C14—C142—H14A	110 (1)
H1B—C1—H1C	110 (2)	C14—C142—H14B	112 (1)
H5A—C5—H5B	109 (2)	C14—C142—H14C	110 (1)
H5A—C5—H5C	107 (2)	H14A—C142—H14B	108 (2)
H5B—C5—H5C	110 (2)	H14A—C142—H14C	108 (2)
C21—C22—H22	119 (1)	H14B—C142—H14C	109 (2)
O31—N31—C3—C2	−176.69 (11)	O131—N131—C13—C12	175.81 (10)
O31—N31—C3—C4	0.0 (2)	O131—N131—C13—C14	−0.17 (18)
C21—C2—C3—N31	−125.33 (13)	C121—C12—C13—N131	127.44 (12)
C1—C2—C3—N31	108.69 (14)	C11—C12—C13—N131	−107.15 (14)
C27—C2—C3—N31	−8.03 (18)	C127—C12—C13—N131	9.72 (16)
C21—C2—C3—C4	58.00 (17)	C121—C12—C13—C14	−56.57 (16)
C1—C2—C3—C4	−67.98 (17)	C11—C12—C13—C14	68.83 (16)
C27—C2—C3—C4	175.30 (14)	C127—C12—C13—C14	−174.30 (13)
N31—C3—C4—C41	58.63 (19)	N131—C13—C14—C142	−55.57 (17)
C2—C3—C4—C41	−125.09 (15)	C12—C13—C14—C142	128.91 (14)
N31—C3—C4—C42	−62.10 (19)	N131—C13—C14—C15	−174.96 (14)
C2—C3—C4—C42	114.18 (15)	C12—C13—C14—C15	9.53 (19)
N31—C3—C4—C5	178.18 (15)	N131—C13—C14—C141	65.16 (19)
C2—C3—C4—C5	−5.5 (2)	C12—C13—C14—C141	−110.36 (16)
C1—C2—C21—C22	169.05 (15)	C11—C12—C121—C122	11.9 (2)
C27—C2—C21—C22	−74.66 (17)	C127—C12—C121—C122	−104.94 (16)
C3—C2—C21—C22	46.19 (18)	C13—C12—C121—C122	134.00 (15)
C1—C2—C21—C26	−15.0 (2)	C11—C12—C121—C126	−170.94 (15)
C27—C2—C21—C26	101.33 (17)	C127—C12—C121—C126	72.26 (17)
C3—C2—C21—C26	−137.82 (14)	C13—C12—C121—C126	−48.80 (17)
C26—C21—C22—C23	1.1 (2)	C126—C121—C122—C123	2.2 (2)
C2—C21—C22—C23	177.25 (15)	C12—C121—C122—C123	179.48 (15)
C21—C22—C23—C24	−0.6 (3)	C121—C122—C123—C124	−1.2 (3)
C22—C23—C24—C25	−0.2 (3)	C122—C123—C124—C125	0.0 (3)
C23—C24—C25—C26	0.5 (3)	C123—C124—C125—C126	0.1 (3)
C24—C25—C26—C21	0.0 (3)	C124—C125—C126—C121	1.1 (3)
C22—C21—C26—C25	−0.8 (2)	C122—C121—C126—C125	−2.2 (2)
C2—C21—C26—C25	−176.85 (15)	C12—C121—C126—C125	−179.56 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···N31^i	0.92 (2)	1.97 (2)	2.8598 (18)	163.4 (19)
O131—H131···N131^ii	0.93 (2)	1.91 (2)	2.7973 (15)	160 (2)

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