2-(9-Anthrylmethyl-ideneamino)-4-methyl-phenol.

The title compound, C(22)H(17)NO, is a novel Schiff base synthesized via a condensation reaction between 9-anthracenecarboxaldehyde and 2-amino-p-cresol. The asymmetric unit contains two independent mol-ecules that are joined by an O-H⋯OH hydrogen bond. An intra-molecular O-H⋯N hydrogen bond occurs in each mol-ecule. π-stacking about inversion centers was observed between adjacent phenol rings [centroid-centroid distance = 3.850 (2) Å] and adjacent anthracene rings [centroid-centroid distance = 3.834 (2) Å]. The C-N=C-C torsion angles between the phenol and anthracene rings are close to 180° with values of 174.06 (15) and 179.85 (14)°.

Related literature

For related structures, see: De et al. (2008 ▶); Ünver et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to the use of luminescent metal complexes formed by Schiff bases in light emitting diode construction and solar energy collection, see: Liao et al. (2009 ▶); Mak et al. (2009 ▶).

Experimental

Crystal data

C22H17NO

M = 311.37

Triclinic,

a = 8.6037 (15) Å

b = 12.839 (3) Å

c = 15.015 (3) Å

α = 94.508 (9)°

β = 97.164 (11)°

γ = 106.490 (11)°

V = 1566.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 90 K

0.37 × 0.15 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

35942 measured reflections

7462 independent reflections

4454 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.127

S = 1.02

7462 reflections

442 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016715/zq2039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016715/zq2039Isup2.hkl

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

C22H17NO	Z = 4
Mr = 311.37	F(000) = 656
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6037 (15) Å	Cell parameters from 7377 reflections
b = 12.839 (3) Å	θ = 2.5–27.8°
c = 15.015 (3) Å	µ = 0.08 mm−1
α = 94.508 (9)°	T = 90 K
β = 97.164 (11)°	Lath, yellow
γ = 106.490 (11)°	0.37 × 0.15 × 0.05 mm
V = 1566.6 (6) Å3

Nonius KappaCCD diffractometer with Oxford Cryostream	4454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 27.9°, θmin = 2.5°
ω scans with κ offsets	h = −11→11
35942 measured reflections	k = −16→16
7462 independent reflections	l = −19→19

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
7462 reflections	Δρmax = 0.30 e Å−3
442 parameters	Δρmin = −0.28 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: 0.0034 (10)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.30490 (15)	0.14730 (11)	0.20434 (9)	0.0223 (3)
H10H	0.261 (2)	0.1946 (17)	0.2172 (14)	0.033*
N1	0.13998 (16)	0.26290 (12)	0.10202 (10)	0.0177 (3)
C1	0.0939 (2)	0.44058 (15)	0.09855 (11)	0.0164 (4)
C2	−0.0671 (2)	0.42007 (15)	0.11964 (11)	0.0167 (4)
C3	−0.1820 (2)	0.31351 (16)	0.10892 (12)	0.0215 (4)
H3	−0.1516	0.2527	0.0851	0.026*
C4	−0.3344 (2)	0.29700 (16)	0.13208 (13)	0.0246 (5)
H4	−0.4084	0.2251	0.1244	0.029*
C5	−0.3837 (2)	0.38605 (17)	0.16758 (13)	0.0249 (5)
H5	−0.4894	0.3733	0.1850	0.030*
C6	−0.2806 (2)	0.48933 (16)	0.17677 (12)	0.0213 (4)
H6	−0.3157	0.5486	0.1994	0.026*
C7	−0.1195 (2)	0.51040 (15)	0.15290 (11)	0.0170 (4)
C8	−0.0120 (2)	0.61631 (15)	0.16377 (12)	0.0196 (4)
H8	−0.0473	0.6754	0.1867	0.023*
C9	0.1462 (2)	0.63784 (15)	0.14184 (12)	0.0181 (4)
C10	0.2576 (2)	0.74645 (16)	0.15396 (13)	0.0237 (4)
H10	0.2225	0.8059	0.1763	0.028*
C11	0.4120 (2)	0.76605 (17)	0.13417 (14)	0.0289 (5)
H11	0.4841	0.8386	0.1425	0.035*
C12	0.4657 (2)	0.67730 (16)	0.10083 (13)	0.0262 (5)
H12	0.5740	0.6911	0.0870	0.031*
C13	0.3642 (2)	0.57331 (16)	0.08864 (13)	0.0222 (4)
H13	0.4031	0.5156	0.0665	0.027*
C14	0.2004 (2)	0.54824 (15)	0.10823 (12)	0.0178 (4)
C15	0.1512 (2)	0.34955 (15)	0.06342 (12)	0.0181 (4)
H15	0.1987	0.3556	0.0095	0.022*
C16	0.1843 (2)	0.17612 (14)	0.05799 (12)	0.0165 (4)
C17	0.2645 (2)	0.11812 (15)	0.11268 (12)	0.0170 (4)
C18	0.3106 (2)	0.03190 (15)	0.07482 (12)	0.0191 (4)
H18	0.3682	−0.0058	0.1120	0.023*
C19	0.2723 (2)	0.00072 (15)	−0.01782 (13)	0.0218 (4)
H19	0.3061	−0.0577	−0.0435	0.026*
C20	0.1853 (2)	0.05329 (15)	−0.07398 (12)	0.0202 (4)
C21	0.1432 (2)	0.14129 (16)	−0.03464 (12)	0.0198 (4)
H21	0.0850	0.1787	−0.0718	0.024*
C22	0.1364 (2)	0.01475 (18)	−0.17348 (13)	0.0316 (5)
H22A	0.0264	−0.0380	−0.1843	0.047*
H22B	0.2149	−0.0203	−0.1943	0.047*
H22C	0.1359	0.0774	−0.2067	0.047*
O2	0.53743 (15)	0.04269 (11)	0.27603 (8)	0.0207 (3)
H20H	0.488 (2)	0.0923 (17)	0.2760 (13)	0.031*
N2	0.52578 (16)	0.20557 (12)	0.39729 (10)	0.0168 (3)
C23	0.48926 (19)	0.38573 (14)	0.40197 (11)	0.0142 (4)
C24	0.3154 (2)	0.35684 (14)	0.38026 (11)	0.0150 (4)
C25	0.2085 (2)	0.25083 (15)	0.38727 (11)	0.0175 (4)
H25	0.2540	0.1949	0.4049	0.021*
C26	0.0420 (2)	0.22873 (15)	0.36905 (12)	0.0197 (4)
H26	−0.0263	0.1578	0.3746	0.024*
C27	−0.0304 (2)	0.30931 (16)	0.34210 (12)	0.0205 (4)
H27	−0.1463	0.2922	0.3290	0.025*
C28	0.0661 (2)	0.41141 (16)	0.33494 (12)	0.0195 (4)
H28	0.0167	0.4656	0.3175	0.023*
C29	0.2409 (2)	0.43844 (15)	0.35330 (11)	0.0161 (4)
C30	0.3395 (2)	0.54295 (15)	0.34506 (11)	0.0172 (4)
H30	0.2891	0.5956	0.3249	0.021*
C31	0.5098 (2)	0.57245 (14)	0.36561 (11)	0.0167 (4)
C32	0.6089 (2)	0.67977 (15)	0.35648 (13)	0.0229 (4)
H32	0.5579	0.7320	0.3359	0.027*
C33	0.7750 (2)	0.70842 (15)	0.37681 (13)	0.0236 (4)
H33	0.8392	0.7804	0.3709	0.028*
C34	0.8524 (2)	0.63117 (15)	0.40679 (12)	0.0211 (4)
H34	0.9686	0.6519	0.4210	0.025*
C35	0.7631 (2)	0.52775 (15)	0.41557 (12)	0.0188 (4)
H35	0.8181	0.4771	0.4350	0.023*
C36	0.5874 (2)	0.49345 (14)	0.39604 (11)	0.0152 (4)
C37	0.5733 (2)	0.30621 (15)	0.43076 (12)	0.0157 (4)
H37	0.6671	0.3307	0.4763	0.019*
C38	0.61304 (19)	0.13383 (14)	0.42820 (12)	0.0145 (4)
C39	0.61383 (19)	0.05028 (15)	0.36290 (12)	0.0157 (4)
C40	0.69549 (19)	−0.02469 (14)	0.38538 (12)	0.0164 (4)
H40	0.6983	−0.0807	0.3409	0.020*
C41	0.77342 (19)	−0.01782 (15)	0.47339 (12)	0.0172 (4)
H41	0.8307	−0.0690	0.4881	0.021*
C42	0.76957 (19)	0.06220 (15)	0.54060 (12)	0.0172 (4)
C43	0.68877 (19)	0.13757 (14)	0.51648 (12)	0.0161 (4)
H43	0.6850	0.1930	0.5612	0.019*
C44	0.8441 (2)	0.06293 (16)	0.63718 (12)	0.0219 (4)
H44A	0.8793	0.1379	0.6678	0.033*
H44B	0.9391	0.0350	0.6380	0.033*
H44C	0.7624	0.0163	0.6685	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0282 (7)	0.0235 (8)	0.0179 (7)	0.0142 (6)	−0.0002 (6)	0.0010 (6)
N1	0.0183 (8)	0.0189 (9)	0.0177 (8)	0.0092 (6)	0.0015 (6)	0.0003 (7)
C1	0.0197 (9)	0.0186 (10)	0.0134 (9)	0.0097 (8)	0.0013 (7)	0.0030 (8)
C2	0.0191 (9)	0.0201 (10)	0.0128 (9)	0.0099 (8)	−0.0006 (7)	0.0029 (8)
C3	0.0212 (10)	0.0212 (11)	0.0224 (10)	0.0094 (8)	0.0001 (8)	−0.0016 (8)
C4	0.0196 (9)	0.0238 (11)	0.0290 (11)	0.0055 (8)	0.0021 (8)	0.0014 (9)
C5	0.0202 (10)	0.0313 (12)	0.0253 (11)	0.0110 (9)	0.0043 (8)	0.0018 (9)
C6	0.0217 (10)	0.0283 (12)	0.0184 (10)	0.0151 (9)	0.0032 (8)	0.0009 (8)
C7	0.0195 (9)	0.0232 (11)	0.0116 (9)	0.0121 (8)	0.0008 (7)	0.0036 (8)
C8	0.0262 (10)	0.0200 (11)	0.0173 (10)	0.0150 (8)	0.0018 (8)	0.0028 (8)
C9	0.0221 (9)	0.0204 (11)	0.0139 (9)	0.0098 (8)	0.0010 (8)	0.0042 (8)
C10	0.0311 (11)	0.0165 (10)	0.0264 (11)	0.0118 (8)	0.0034 (9)	0.0034 (9)
C11	0.0289 (11)	0.0217 (12)	0.0369 (13)	0.0070 (9)	0.0053 (9)	0.0087 (10)
C12	0.0225 (10)	0.0264 (12)	0.0333 (12)	0.0099 (9)	0.0077 (9)	0.0095 (10)
C13	0.0240 (10)	0.0228 (11)	0.0248 (11)	0.0136 (8)	0.0051 (8)	0.0062 (9)
C14	0.0217 (9)	0.0201 (11)	0.0138 (9)	0.0103 (8)	0.0006 (7)	0.0038 (8)
C15	0.0162 (9)	0.0228 (11)	0.0162 (10)	0.0077 (8)	0.0013 (7)	0.0021 (8)
C16	0.0151 (8)	0.0163 (10)	0.0194 (10)	0.0056 (7)	0.0054 (7)	0.0016 (8)
C17	0.0163 (9)	0.0159 (10)	0.0176 (10)	0.0033 (7)	0.0029 (8)	0.0000 (8)
C18	0.0176 (9)	0.0169 (10)	0.0232 (11)	0.0067 (8)	0.0002 (8)	0.0030 (8)
C19	0.0168 (9)	0.0189 (11)	0.0287 (11)	0.0045 (8)	0.0057 (8)	−0.0043 (9)
C20	0.0148 (9)	0.0242 (11)	0.0191 (10)	0.0030 (8)	0.0034 (8)	−0.0034 (8)
C21	0.0166 (9)	0.0244 (11)	0.0188 (10)	0.0060 (8)	0.0027 (8)	0.0052 (8)
C22	0.0275 (11)	0.0411 (14)	0.0234 (11)	0.0081 (10)	0.0041 (9)	−0.0059 (10)
O2	0.0236 (7)	0.0198 (8)	0.0208 (7)	0.0118 (6)	−0.0003 (6)	0.0000 (6)
N2	0.0180 (8)	0.0160 (9)	0.0193 (8)	0.0086 (6)	0.0051 (6)	0.0032 (7)
C23	0.0185 (9)	0.0141 (10)	0.0117 (9)	0.0076 (7)	0.0028 (7)	0.0001 (7)
C24	0.0202 (9)	0.0162 (10)	0.0101 (9)	0.0083 (7)	0.0025 (7)	−0.0003 (7)
C25	0.0201 (9)	0.0177 (10)	0.0179 (10)	0.0092 (8)	0.0052 (8)	0.0036 (8)
C26	0.0195 (9)	0.0170 (10)	0.0214 (10)	0.0032 (8)	0.0048 (8)	0.0000 (8)
C27	0.0148 (9)	0.0281 (12)	0.0193 (10)	0.0085 (8)	0.0007 (8)	0.0017 (8)
C28	0.0213 (9)	0.0255 (11)	0.0157 (10)	0.0142 (8)	0.0006 (8)	0.0021 (8)
C29	0.0210 (9)	0.0204 (10)	0.0095 (9)	0.0107 (8)	0.0021 (7)	0.0003 (8)
C30	0.0250 (10)	0.0163 (10)	0.0150 (9)	0.0127 (8)	0.0043 (8)	0.0036 (8)
C31	0.0243 (9)	0.0143 (10)	0.0139 (9)	0.0079 (8)	0.0060 (8)	0.0017 (8)
C32	0.0314 (11)	0.0156 (10)	0.0249 (11)	0.0096 (8)	0.0087 (9)	0.0049 (8)
C33	0.0300 (11)	0.0115 (10)	0.0286 (11)	0.0031 (8)	0.0100 (9)	0.0006 (8)
C34	0.0199 (9)	0.0191 (11)	0.0218 (10)	0.0027 (8)	0.0053 (8)	−0.0039 (8)
C35	0.0209 (9)	0.0195 (10)	0.0176 (10)	0.0084 (8)	0.0048 (8)	0.0005 (8)
C36	0.0208 (9)	0.0131 (10)	0.0120 (9)	0.0056 (7)	0.0042 (7)	−0.0006 (7)
C37	0.0154 (9)	0.0185 (10)	0.0145 (9)	0.0067 (7)	0.0028 (7)	0.0021 (8)
C38	0.0128 (8)	0.0126 (9)	0.0201 (10)	0.0048 (7)	0.0060 (7)	0.0049 (8)
C39	0.0124 (8)	0.0190 (10)	0.0149 (9)	0.0028 (7)	0.0023 (7)	0.0036 (8)
C40	0.0161 (9)	0.0135 (10)	0.0216 (10)	0.0058 (7)	0.0071 (8)	0.0023 (8)
C41	0.0136 (8)	0.0162 (10)	0.0254 (10)	0.0064 (7)	0.0071 (8)	0.0089 (8)
C42	0.0127 (8)	0.0193 (10)	0.0209 (10)	0.0039 (7)	0.0059 (7)	0.0076 (8)
C43	0.0157 (9)	0.0134 (10)	0.0190 (10)	0.0037 (7)	0.0043 (7)	0.0007 (8)
C44	0.0210 (9)	0.0244 (11)	0.0224 (11)	0.0087 (8)	0.0040 (8)	0.0069 (9)

O1—C17	1.371 (2)	O2—C39	1.368 (2)
O1—H10H	0.82 (2)	O2—H20H	0.86 (2)
N1—C15	1.280 (2)	N2—C37	1.279 (2)
N1—C16	1.419 (2)	N2—C38	1.414 (2)
C1—C14	1.410 (2)	C23—C36	1.417 (2)
C1—C2	1.416 (2)	C23—C24	1.423 (2)
C1—C15	1.477 (2)	C23—C37	1.470 (2)
C2—C3	1.426 (2)	C24—C25	1.430 (2)
C2—C7	1.435 (2)	C24—C29	1.434 (2)
C3—C4	1.361 (2)	C25—C26	1.366 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.417 (3)	C26—C27	1.411 (3)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.356 (3)	C27—C28	1.359 (3)
C5—H5	0.9500	C27—H27	0.9500
C6—C7	1.431 (2)	C28—C29	1.429 (2)
C6—H6	0.9500	C28—H28	0.9500
C7—C8	1.395 (2)	C29—C30	1.393 (2)
C8—C9	1.396 (2)	C30—C31	1.393 (2)
C8—H8	0.9500	C30—H30	0.9500
C9—C10	1.433 (3)	C31—C32	1.427 (2)
C9—C14	1.438 (2)	C31—C36	1.437 (2)
C10—C11	1.355 (3)	C32—C33	1.359 (3)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.425 (3)	C33—C34	1.414 (3)
C11—H11	0.9500	C33—H33	0.9500
C12—C13	1.356 (3)	C34—C35	1.358 (2)
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.427 (2)	C35—C36	1.434 (2)
C13—H13	0.9500	C35—H35	0.9500
C15—H15	0.9500	C37—H37	0.9500
C16—C21	1.396 (2)	C38—C43	1.393 (2)
C16—C17	1.397 (2)	C38—C39	1.397 (2)
C17—C18	1.383 (2)	C39—C40	1.382 (2)
C18—C19	1.388 (3)	C40—C41	1.389 (2)
C18—H18	0.9500	C40—H40	0.9500
C19—C20	1.395 (3)	C41—C42	1.393 (2)
C19—H19	0.9500	C41—H41	0.9500
C20—C21	1.392 (2)	C42—C43	1.388 (2)
C20—C22	1.504 (3)	C42—C44	1.509 (2)
C21—H21	0.9500	C43—H43	0.9500
C22—H22A	0.9800	C44—H44A	0.9800
C22—H22B	0.9800	C44—H44B	0.9800
C22—H22C	0.9800	C44—H44C	0.9800
C17—O1—H10H	106.8 (15)	C39—O2—H20H	105.9 (14)
C15—N1—C16	118.53 (15)	C37—N2—C38	119.84 (15)
C14—C1—C2	120.64 (16)	C36—C23—C24	120.39 (16)
C14—C1—C15	118.97 (15)	C36—C23—C37	117.76 (15)
C2—C1—C15	120.36 (16)	C24—C23—C37	121.85 (16)
C1—C2—C3	123.32 (16)	C23—C24—C25	123.46 (16)
C1—C2—C7	119.01 (16)	C23—C24—C29	119.12 (16)
C3—C2—C7	117.67 (15)	C25—C24—C29	117.37 (15)
C4—C3—C2	121.46 (18)	C26—C25—C24	121.06 (17)
C4—C3—H3	119.3	C26—C25—H25	119.5
C2—C3—H3	119.3	C24—C25—H25	119.5
C3—C4—C5	120.64 (18)	C25—C26—C27	121.23 (17)
C3—C4—H4	119.7	C25—C26—H26	119.4
C5—C4—H4	119.7	C27—C26—H26	119.4
C6—C5—C4	120.15 (17)	C28—C27—C26	119.87 (16)
C6—C5—H5	119.9	C28—C27—H27	120.1
C4—C5—H5	119.9	C26—C27—H27	120.1
C5—C6—C7	121.02 (18)	C27—C28—C29	120.93 (17)
C5—C6—H6	119.5	C27—C28—H28	119.5
C7—C6—H6	119.5	C29—C28—H28	119.5
C8—C7—C6	121.19 (17)	C30—C29—C28	120.78 (16)
C8—C7—C2	119.78 (15)	C30—C29—C24	119.70 (15)
C6—C7—C2	119.00 (16)	C28—C29—C24	119.53 (16)
C7—C8—C9	121.78 (17)	C31—C30—C29	121.87 (16)
C7—C8—H8	119.1	C31—C30—H30	119.1
C9—C8—H8	119.1	C29—C30—H30	119.1
C8—C9—C10	121.89 (17)	C30—C31—C32	121.12 (17)
C8—C9—C14	119.11 (16)	C30—C31—C36	119.56 (16)
C10—C9—C14	118.98 (16)	C32—C31—C36	119.32 (16)
C11—C10—C9	121.35 (18)	C33—C32—C31	121.00 (18)
C11—C10—H10	119.3	C33—C32—H32	119.5
C9—C10—H10	119.3	C31—C32—H32	119.5
C10—C11—C12	119.68 (18)	C32—C33—C34	120.05 (17)
C10—C11—H11	120.2	C32—C33—H33	120.0
C12—C11—H11	120.2	C34—C33—H33	120.0
C13—C12—C11	120.79 (17)	C35—C34—C33	120.98 (17)
C13—C12—H12	119.6	C35—C34—H34	119.5
C11—C12—H12	119.6	C33—C34—H34	119.5
C12—C13—C14	121.78 (18)	C34—C35—C36	121.33 (17)
C12—C13—H13	119.1	C34—C35—H35	119.3
C14—C13—H13	119.1	C36—C35—H35	119.3
C1—C14—C13	122.90 (17)	C23—C36—C35	123.36 (16)
C1—C14—C9	119.66 (15)	C23—C36—C31	119.28 (15)
C13—C14—C9	117.42 (16)	C35—C36—C31	117.32 (16)
N1—C15—C1	123.23 (16)	N2—C37—C23	122.99 (16)
N1—C15—H15	118.4	N2—C37—H37	118.5
C1—C15—H15	118.4	C23—C37—H37	118.5
C21—C16—C17	118.71 (16)	C43—C38—C39	119.36 (16)
C21—C16—N1	124.14 (16)	C43—C38—N2	125.80 (16)
C17—C16—N1	117.01 (15)	C39—C38—N2	114.77 (16)
O1—C17—C18	118.31 (16)	O2—C39—C40	119.20 (16)
O1—C17—C16	121.24 (16)	O2—C39—C38	120.91 (16)
C18—C17—C16	120.41 (16)	C40—C39—C38	119.88 (16)
C17—C18—C19	119.72 (17)	C39—C40—C41	119.70 (17)
C17—C18—H18	120.1	C39—C40—H40	120.2
C19—C18—H18	120.1	C41—C40—H40	120.2
C18—C19—C20	121.45 (17)	C40—C41—C42	121.63 (17)
C18—C19—H19	119.3	C40—C41—H41	119.2
C20—C19—H19	119.3	C42—C41—H41	119.2
C21—C20—C19	117.80 (17)	C43—C42—C41	117.83 (17)
C21—C20—C22	121.23 (18)	C43—C42—C44	121.43 (17)
C19—C20—C22	120.97 (17)	C41—C42—C44	120.68 (16)
C20—C21—C16	121.79 (17)	C42—C43—C38	121.54 (17)
C20—C21—H21	119.1	C42—C43—H43	119.2
C16—C21—H21	119.1	C38—C43—H43	119.2
C20—C22—H22A	109.5	C42—C44—H44A	109.5
C20—C22—H22B	109.5	C42—C44—H44B	109.5
H22A—C22—H22B	109.5	H44A—C44—H44B	109.5
C20—C22—H22C	109.5	C42—C44—H44C	109.5
H22A—C22—H22C	109.5	H44A—C44—H44C	109.5
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
C14—C1—C2—C3	178.20 (16)	C36—C23—C24—C25	−178.08 (15)
C15—C1—C2—C3	0.0 (3)	C37—C23—C24—C25	2.1 (3)
C14—C1—C2—C7	−1.3 (3)	C36—C23—C24—C29	−0.7 (2)
C15—C1—C2—C7	−179.45 (16)	C37—C23—C24—C29	179.52 (16)
C1—C2—C3—C4	178.37 (17)	C23—C24—C25—C26	177.33 (16)
C7—C2—C3—C4	−2.1 (3)	C29—C24—C25—C26	−0.1 (2)
C2—C3—C4—C5	0.2 (3)	C24—C25—C26—C27	0.5 (3)
C3—C4—C5—C6	1.6 (3)	C25—C26—C27—C28	−0.8 (3)
C4—C5—C6—C7	−1.4 (3)	C26—C27—C28—C29	0.8 (3)
C5—C6—C7—C8	−178.84 (17)	C27—C28—C29—C30	179.40 (17)
C5—C6—C7—C2	−0.6 (3)	C27—C28—C29—C24	−0.4 (2)
C1—C2—C7—C8	0.1 (2)	C23—C24—C29—C30	2.7 (2)
C3—C2—C7—C8	−179.44 (16)	C25—C24—C29—C30	−179.73 (16)
C1—C2—C7—C6	−178.15 (16)	C23—C24—C29—C28	−177.46 (15)
C3—C2—C7—C6	2.3 (2)	C25—C24—C29—C28	0.1 (2)
C6—C7—C8—C9	179.17 (17)	C28—C29—C30—C31	177.71 (15)
C2—C7—C8—C9	1.0 (3)	C24—C29—C30—C31	−2.5 (3)
C7—C8—C9—C10	−179.25 (17)	C29—C30—C31—C32	179.78 (16)
C7—C8—C9—C14	−0.8 (3)	C29—C30—C31—C36	0.1 (3)
C8—C9—C10—C11	178.62 (18)	C30—C31—C32—C33	179.82 (17)
C14—C9—C10—C11	0.2 (3)	C36—C31—C32—C33	−0.5 (3)
C9—C10—C11—C12	−0.2 (3)	C31—C32—C33—C34	0.5 (3)
C10—C11—C12—C13	0.0 (3)	C32—C33—C34—C35	0.2 (3)
C11—C12—C13—C14	0.2 (3)	C33—C34—C35—C36	−0.9 (3)
C2—C1—C14—C13	179.46 (16)	C24—C23—C36—C35	−179.05 (15)
C15—C1—C14—C13	−2.3 (3)	C37—C23—C36—C35	0.8 (2)
C2—C1—C14—C9	1.5 (3)	C24—C23—C36—C31	−1.6 (2)
C15—C1—C14—C9	179.64 (16)	C37—C23—C36—C31	178.21 (16)
C12—C13—C14—C1	−178.18 (17)	C34—C35—C36—C23	178.33 (16)
C12—C13—C14—C9	−0.1 (3)	C34—C35—C36—C31	0.8 (2)
C8—C9—C14—C1	−0.4 (3)	C30—C31—C36—C23	1.9 (2)
C10—C9—C14—C1	178.07 (16)	C32—C31—C36—C23	−177.74 (15)
C8—C9—C14—C13	−178.52 (17)	C30—C31—C36—C35	179.50 (15)
C10—C9—C14—C13	0.0 (2)	C32—C31—C36—C35	−0.1 (2)
C16—N1—C15—C1	174.06 (15)	C38—N2—C37—C23	179.85 (14)
C14—C1—C15—N1	130.13 (19)	C36—C23—C37—N2	−142.22 (16)
C2—C1—C15—N1	−51.7 (3)	C24—C23—C37—N2	37.6 (2)
C15—N1—C16—C21	−41.7 (2)	C37—N2—C38—C43	35.3 (2)
C15—N1—C16—C17	142.73 (16)	C37—N2—C38—C39	−147.70 (15)
C21—C16—C17—O1	−178.70 (15)	C43—C38—C39—O2	178.51 (14)
N1—C16—C17—O1	−2.9 (2)	N2—C38—C39—O2	1.3 (2)
C21—C16—C17—C18	3.7 (2)	C43—C38—C39—C40	−2.8 (2)
N1—C16—C17—C18	179.53 (15)	N2—C38—C39—C40	179.93 (14)
O1—C17—C18—C19	−179.66 (15)	O2—C39—C40—C41	−179.96 (14)
C16—C17—C18—C19	−2.0 (2)	C38—C39—C40—C41	1.4 (2)
C17—C18—C19—C20	−1.2 (3)	C39—C40—C41—C42	1.0 (2)
C18—C19—C20—C21	2.4 (2)	C40—C41—C42—C43	−1.8 (2)
C18—C19—C20—C22	−176.54 (16)	C40—C41—C42—C44	175.37 (15)
C19—C20—C21—C16	−0.6 (2)	C41—C42—C43—C38	0.2 (2)
C22—C20—C21—C16	178.34 (16)	C44—C42—C43—C38	−176.88 (15)
C17—C16—C21—C20	−2.4 (2)	C39—C38—C43—C42	2.0 (2)
N1—C16—C21—C20	−177.88 (15)	N2—C38—C43—C42	178.95 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10H···N1	0.82 (2)	2.27 (2)	2.754 (2)	118.0 (17)
O2—H20H···O1	0.86 (2)	2.11 (2)	2.8602 (18)	144.9 (18)
O2—H20H···N2	0.86 (2)	2.17 (2)	2.695 (2)	119.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10H⋯N1	0.82 (2)	2.27 (2)	2.754 (2)	118.0 (17)
O2—H20H⋯O1	0.86 (2)	2.11 (2)	2.8602 (18)	144.9 (18)
O2—H20H⋯N2	0.86 (2)	2.17 (2)	2.695 (2)	119.1 (17)