4-Hydr­oxy-4-methyl-6-phenyl-2-p-tolyl-5,6-dihydro-4H-1,3-selenazine

In the title crystal structure, C₁₈H₁₉NOSe, there are two mol­ecules in the asymmetric unit. Pairs of molecules are linked into a centrosymmetric dimer via inter­molecular O—H...N hydrogen bonds [O...N = 2.872 (2) and 2.893 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 190 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.030
• wR factor = 0.068
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-Hydroxy-4-methyl-6-phenyl-2-p-tolyl-5,6-dihydro-4H-1,3-selenazine

Crystal data

C18H19NOSe	F(000) = 1408
Mr = 344.30	Dx = 1.412 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13476 reflections
a = 18.0846 (10) Å	θ = 2.9–27.5°
b = 16.9821 (10) Å	µ = 2.32 mm^−1
c = 10.8354 (10) Å	T = 190 K
β = 103.19 (1)°	Prism, colorless
V = 3239.9 (4) Å^3	0.32 × 0.20 × 0.10 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	7417 independent reflections
Radiation source: fine-focus sealed tube	6160 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
φ scans and ω scans with κ offsets	h = −23→23
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −22→20
Tmin = 0.524, Tmax = 0.801	l = −14→14
26451 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0236P)^2 + 1.8946P] where P = (Fo^2 + 2Fc^2)/3
7417 reflections	(Δ/σ)max = 0.003
387 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

Experimental. IR (KBr) 3260, 1597 cm^-1; UV/Vis (CH₂Cl₂) λ_max [log (ε/dm³ mol^-1 cm^-1)]: 342 (2.59), 259 (4.08); ¹H NMR (400 MHz, CDCl₃): δ 1.49 (3H, s, CH₃), 1.96 (1H, t, J = 13.6 Hz), 2.19 (1H, dd, J = 4.4, 13.6 Hz), 2.36 (3H, s, CH₃), 3.13 (1H, br, OH), 4.69 (1H, dd, J = 4.4, 13.6 Hz, C6), 7.18 (2H, d, J = 7.8 Hz, Ar), 7.24–7.29 (1H, m, Ar), 7.33–7.38 (4H, m, Ar), 7.66 (2H, d, J = 7.8 Hz, Ar); ¹³C NMR (100 MHz, CDCl₃): δ 21.4, 24.9, 38.6, 40.2, 88.4, 126.6, 127.7, 127.9, 128.9, 129.1, 136.9, 140.9, 141.1, 157.6; ⁷⁷Se NMR (76 MHz, CDCl₃): δ 387.4.

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.

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

	x	y	z	Uiso*/Ueq
Se1	0.264428 (11)	0.035403 (13)	0.47358 (2)	0.03695 (7)
C1	0.35666 (10)	0.06704 (11)	0.42828 (18)	0.0269 (4)
N1	0.40879 (8)	0.02311 (9)	0.40645 (15)	0.0259 (3)
C2	0.40720 (10)	−0.06372 (11)	0.41437 (19)	0.0272 (4)
C3	0.32762 (10)	−0.09914 (11)	0.37988 (19)	0.0283 (4)
H1	0.3012	−0.0797	0.2951	0.034*
H2	0.3319	−0.1571	0.3745	0.034*
C4	0.27990 (11)	−0.07933 (12)	0.47459 (19)	0.0293 (4)
H3	0.3087	−0.0953	0.5610	0.035*
C5	0.36355 (10)	0.15365 (11)	0.41577 (18)	0.0273 (4)
C6	0.33480 (11)	0.20683 (12)	0.4910 (2)	0.0327 (4)
H4	0.3079	0.1879	0.5507	0.039*
C7	0.34519 (12)	0.28696 (12)	0.4793 (2)	0.0368 (5)
H5	0.3253	0.3224	0.5314	0.044*
C8	0.38405 (12)	0.31663 (12)	0.3927 (2)	0.0367 (5)
C9	0.41108 (11)	0.26344 (12)	0.3165 (2)	0.0356 (5)
H6	0.4369	0.2825	0.2553	0.043*
C10	0.40132 (11)	0.18334 (12)	0.32751 (19)	0.0314 (4)
H7	0.4206	0.1482	0.2743	0.038*
C11	0.39684 (15)	0.40387 (13)	0.3814 (3)	0.0561 (7)
H8	0.4514	0.4150	0.4045	0.084*
H9	0.3714	0.4325	0.4384	0.084*
H10	0.3760	0.4207	0.2938	0.084*
O1	0.43975 (7)	−0.08583 (8)	0.54133 (13)	0.0316 (3)
H11	0.4850	−0.0703	0.5615	0.046 (7)*
C12	0.45430 (12)	−0.09404 (13)	0.3247 (2)	0.0379 (5)
H12	0.4302	−0.0786	0.2376	0.057*
H13	0.4576	−0.1516	0.3302	0.057*
H14	0.5055	−0.0714	0.3483	0.057*
C13	0.20361 (10)	−0.11978 (11)	0.44733 (19)	0.0287 (4)
C14	0.18347 (11)	−0.16600 (12)	0.5404 (2)	0.0352 (5)
H15	0.2164	−0.1691	0.6222	0.042*
C15	0.11585 (13)	−0.20763 (13)	0.5147 (2)	0.0429 (5)
H16	0.1028	−0.2393	0.5788	0.052*
C16	0.06738 (12)	−0.20328 (13)	0.3966 (2)	0.0414 (5)
H17	0.0213	−0.2324	0.3788	0.050*
C17	0.08616 (12)	−0.15642 (14)	0.3044 (2)	0.0414 (5)
H18	0.0526	−0.1527	0.2232	0.050*
C18	0.15385 (11)	−0.11468 (13)	0.3296 (2)	0.0375 (5)
H19	0.1662	−0.0823	0.2656	0.045*
Se2	0.237195 (11)	0.485348 (12)	0.55498 (2)	0.03079 (6)
C19	0.13948 (10)	0.43604 (11)	0.50247 (17)	0.0239 (4)
N2	0.07842 (9)	0.46638 (9)	0.43962 (15)	0.0259 (3)
C20	0.07275 (10)	0.55030 (11)	0.40073 (19)	0.0274 (4)
C21	0.14450 (10)	0.58368 (11)	0.36836 (19)	0.0291 (4)
H20	0.1593	0.5493	0.3042	0.035*
H21	0.1328	0.6364	0.3298	0.035*
C22	0.21157 (10)	0.59093 (11)	0.48163 (19)	0.0285 (4)
H22	0.1961	0.6249	0.5469	0.034*
C23	0.14158 (10)	0.35199 (11)	0.54131 (18)	0.0250 (4)
C24	0.18222 (11)	0.32706 (12)	0.65996 (19)	0.0331 (4)
H23	0.2109	0.3641	0.7172	0.040*
C25	0.18103 (12)	0.24883 (12)	0.6949 (2)	0.0362 (5)
H24	0.2086	0.2330	0.7766	0.043*
C26	0.14070 (12)	0.19316 (12)	0.6136 (2)	0.0340 (5)
C27	0.10213 (12)	0.21771 (12)	0.4942 (2)	0.0355 (5)
H25	0.0753	0.1801	0.4358	0.043*
C28	0.10189 (11)	0.29608 (11)	0.45823 (19)	0.0298 (4)
H26	0.0744	0.3117	0.3764	0.036*
C29	0.13594 (15)	0.10894 (13)	0.6558 (3)	0.0480 (6)
H27	0.1276	0.0741	0.5819	0.072*
H28	0.0937	0.1036	0.6979	0.072*
H29	0.1835	0.0945	0.7151	0.072*
O2	0.05925 (7)	0.59517 (8)	0.50362 (13)	0.0312 (3)
H30	0.0185	0.5803	0.5211	0.041 (7)*
C30	0.00638 (11)	0.55635 (13)	0.2862 (2)	0.0359 (5)
H31	0.0185	0.5277	0.2148	0.054*
H32	−0.0031	0.6118	0.2631	0.054*
H33	−0.0390	0.5334	0.3068	0.054*
C31	0.28382 (11)	0.62408 (11)	0.45408 (19)	0.0300 (4)
C32	0.32394 (12)	0.68126 (12)	0.5337 (2)	0.0371 (5)
H34	0.3048	0.7005	0.6026	0.045*
C33	0.39192 (13)	0.71047 (14)	0.5133 (3)	0.0478 (6)
H35	0.4188	0.7499	0.5678	0.057*
C34	0.42033 (13)	0.68265 (15)	0.4148 (3)	0.0495 (6)
H36	0.4671	0.7024	0.4017	0.059*
C35	0.38109 (12)	0.62601 (15)	0.3347 (2)	0.0449 (6)
H37	0.4006	0.6070	0.2660	0.054*
C36	0.31314 (11)	0.59673 (13)	0.3543 (2)	0.0362 (5)
H38	0.2864	0.5576	0.2990	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.02869 (11)	0.03553 (12)	0.05278 (15)	−0.00439 (8)	0.02206 (10)	−0.00551 (9)
C1	0.0201 (9)	0.0343 (11)	0.0265 (10)	−0.0038 (8)	0.0055 (7)	−0.0004 (8)
N1	0.0190 (7)	0.0288 (8)	0.0301 (9)	−0.0016 (6)	0.0058 (6)	0.0021 (7)
C2	0.0205 (9)	0.0286 (10)	0.0326 (11)	−0.0014 (7)	0.0064 (8)	0.0000 (8)
C3	0.0227 (9)	0.0291 (10)	0.0329 (11)	−0.0017 (8)	0.0059 (8)	−0.0005 (8)
C4	0.0249 (9)	0.0339 (11)	0.0295 (11)	−0.0048 (8)	0.0069 (8)	0.0026 (8)
C5	0.0206 (9)	0.0319 (10)	0.0278 (10)	−0.0001 (8)	0.0020 (7)	0.0005 (8)
C6	0.0296 (10)	0.0352 (11)	0.0351 (11)	0.0004 (8)	0.0107 (9)	−0.0001 (9)
C7	0.0335 (11)	0.0329 (11)	0.0457 (13)	0.0051 (9)	0.0126 (9)	−0.0027 (9)
C8	0.0305 (11)	0.0320 (11)	0.0469 (13)	0.0014 (9)	0.0074 (9)	0.0052 (9)
C9	0.0315 (11)	0.0368 (12)	0.0408 (12)	0.0006 (9)	0.0126 (9)	0.0092 (9)
C10	0.0276 (10)	0.0335 (11)	0.0342 (11)	0.0029 (8)	0.0092 (8)	0.0020 (9)
C11	0.0615 (17)	0.0327 (13)	0.081 (2)	0.0024 (12)	0.0318 (15)	0.0055 (12)
O1	0.0193 (7)	0.0367 (8)	0.0369 (8)	−0.0020 (6)	0.0027 (6)	0.0077 (6)
C12	0.0299 (11)	0.0390 (12)	0.0481 (13)	−0.0031 (9)	0.0160 (9)	−0.0071 (10)
C13	0.0219 (9)	0.0317 (10)	0.0335 (11)	−0.0008 (8)	0.0083 (8)	0.0016 (8)
C14	0.0296 (11)	0.0390 (12)	0.0377 (12)	−0.0018 (9)	0.0089 (9)	0.0066 (9)
C15	0.0391 (12)	0.0423 (13)	0.0524 (15)	−0.0069 (10)	0.0210 (11)	0.0082 (11)
C16	0.0268 (11)	0.0409 (13)	0.0578 (15)	−0.0098 (9)	0.0126 (10)	−0.0050 (11)
C17	0.0245 (10)	0.0544 (14)	0.0432 (13)	−0.0047 (10)	0.0036 (9)	−0.0009 (11)
C18	0.0258 (10)	0.0486 (13)	0.0384 (12)	−0.0054 (9)	0.0078 (9)	0.0088 (10)
Se2	0.02259 (10)	0.03010 (11)	0.03729 (12)	−0.00358 (8)	0.00190 (8)	0.00563 (8)
C19	0.0214 (9)	0.0278 (10)	0.0234 (9)	−0.0024 (7)	0.0069 (7)	−0.0020 (7)
N2	0.0237 (8)	0.0256 (8)	0.0287 (9)	0.0003 (6)	0.0067 (6)	0.0005 (6)
C20	0.0254 (9)	0.0242 (10)	0.0331 (11)	0.0020 (7)	0.0073 (8)	0.0017 (8)
C21	0.0266 (10)	0.0270 (10)	0.0349 (11)	0.0014 (8)	0.0096 (8)	0.0051 (8)
C22	0.0281 (10)	0.0246 (10)	0.0345 (11)	−0.0022 (8)	0.0109 (8)	−0.0007 (8)
C23	0.0197 (9)	0.0276 (10)	0.0292 (10)	−0.0005 (7)	0.0087 (7)	0.0002 (8)
C24	0.0295 (10)	0.0371 (11)	0.0302 (11)	−0.0041 (9)	0.0016 (8)	0.0022 (9)
C25	0.0326 (11)	0.0387 (12)	0.0365 (12)	0.0037 (9)	0.0066 (9)	0.0120 (9)
C26	0.0341 (11)	0.0297 (11)	0.0447 (13)	0.0060 (9)	0.0223 (10)	0.0069 (9)
C27	0.0404 (12)	0.0281 (11)	0.0412 (13)	−0.0046 (9)	0.0162 (10)	−0.0042 (9)
C28	0.0290 (10)	0.0290 (10)	0.0308 (11)	−0.0009 (8)	0.0057 (8)	0.0013 (8)
C29	0.0607 (15)	0.0298 (12)	0.0643 (16)	0.0080 (11)	0.0367 (13)	0.0117 (11)
O2	0.0262 (7)	0.0294 (7)	0.0411 (8)	−0.0017 (6)	0.0140 (6)	−0.0045 (6)
C30	0.0292 (10)	0.0379 (11)	0.0377 (12)	0.0031 (9)	0.0015 (9)	0.0058 (9)
C31	0.0253 (9)	0.0261 (10)	0.0380 (12)	−0.0009 (8)	0.0062 (8)	0.0065 (8)
C32	0.0334 (11)	0.0293 (11)	0.0459 (13)	−0.0022 (9)	0.0034 (9)	0.0044 (9)
C33	0.0346 (12)	0.0366 (13)	0.0648 (17)	−0.0110 (10)	−0.0042 (11)	0.0105 (11)
C34	0.0264 (11)	0.0541 (15)	0.0670 (17)	−0.0053 (10)	0.0090 (11)	0.0266 (13)
C35	0.0336 (12)	0.0574 (15)	0.0462 (14)	0.0010 (11)	0.0144 (10)	0.0158 (11)
C36	0.0294 (11)	0.0389 (12)	0.0403 (12)	−0.0026 (9)	0.0077 (9)	0.0036 (9)

Geometric parameters (Å, º)

Se1—C1	1.9197 (18)	Se2—C19	1.9206 (18)
Se1—C4	1.968 (2)	Se2—C22	1.9731 (19)
C1—N1	1.266 (2)	C19—N2	1.267 (2)
C1—C5	1.485 (3)	C19—C23	1.486 (3)
N1—C2	1.478 (2)	N2—C20	1.483 (2)
C2—O1	1.418 (2)	C20—O2	1.417 (2)
C2—C12	1.521 (3)	C20—C30	1.520 (3)
C2—C3	1.525 (2)	C20—C21	1.528 (2)
C3—C4	1.522 (3)	C21—C22	1.521 (3)
C3—H1	0.9900	C21—H20	0.9900
C3—H2	0.9900	C21—H21	0.9900
C4—C13	1.509 (3)	C22—C31	1.514 (3)
C4—H3	1.0000	C22—H22	1.0000
C5—C10	1.390 (3)	C23—C28	1.390 (3)
C5—C6	1.394 (3)	C23—C24	1.393 (3)
C6—C7	1.384 (3)	C24—C25	1.383 (3)
C6—H4	0.9500	C24—H23	0.9500
C7—C8	1.388 (3)	C25—C26	1.382 (3)
C7—H5	0.9500	C25—H24	0.9500
C8—C9	1.386 (3)	C26—C27	1.387 (3)
C8—C11	1.509 (3)	C26—C29	1.510 (3)
C9—C10	1.380 (3)	C27—C28	1.387 (3)
C9—H6	0.9500	C27—H25	0.9500
C10—H7	0.9500	C28—H26	0.9500
C11—H8	0.9800	C29—H27	0.9800
C11—H9	0.9800	C29—H28	0.9800
C11—H10	0.9800	C29—H29	0.9800
O1—H11	0.8400	O2—H30	0.8400
C12—H12	0.9800	C30—H31	0.9800
C12—H13	0.9800	C30—H32	0.9800
C12—H14	0.9800	C30—H33	0.9800
C13—C18	1.386 (3)	C31—C36	1.388 (3)
C13—C14	1.390 (3)	C31—C32	1.388 (3)
C14—C15	1.385 (3)	C32—C33	1.389 (3)
C14—H15	0.9500	C32—H34	0.9500
C15—C16	1.378 (3)	C33—C34	1.370 (4)
C15—H16	0.9500	C33—H35	0.9500
C16—C17	1.379 (3)	C34—C35	1.379 (4)
C16—H17	0.9500	C34—H36	0.9500
C17—C18	1.387 (3)	C35—C36	1.386 (3)
C17—H18	0.9500	C35—H37	0.9500
C18—H19	0.9500	C36—H38	0.9500
C1—Se1—C4	98.50 (8)	C19—Se2—C22	99.28 (8)
N1—C1—C5	119.01 (16)	N2—C19—C23	120.36 (16)
N1—C1—Se1	127.61 (15)	N2—C19—Se2	127.74 (14)
C5—C1—Se1	113.36 (13)	C23—C19—Se2	111.87 (13)
C1—N1—C2	123.50 (15)	C19—N2—C20	122.60 (16)
O1—C2—N1	108.14 (15)	O2—C20—N2	107.84 (15)
O1—C2—C12	111.18 (16)	O2—C20—C30	111.12 (16)
N1—C2—C12	106.23 (15)	N2—C20—C30	106.71 (16)
O1—C2—C3	107.03 (15)	O2—C20—C21	106.79 (15)
N1—C2—C3	114.14 (15)	N2—C20—C21	114.48 (15)
C12—C2—C3	110.16 (16)	C30—C20—C21	109.94 (16)
C4—C3—C2	113.34 (16)	C22—C21—C20	114.04 (16)
C4—C3—H1	108.9	C22—C21—H20	108.7
C2—C3—H1	108.9	C20—C21—H20	108.7
C4—C3—H2	108.9	C22—C21—H21	108.7
C2—C3—H2	108.9	C20—C21—H21	108.7
H1—C3—H2	107.7	H20—C21—H21	107.6
C13—C4—C3	113.66 (16)	C31—C22—C21	115.87 (16)
C13—C4—Se1	109.10 (13)	C31—C22—Se2	106.47 (12)
C3—C4—Se1	108.48 (13)	C21—C22—Se2	108.80 (13)
C13—C4—H3	108.5	C31—C22—H22	108.5
C3—C4—H3	108.5	C21—C22—H22	108.5
Se1—C4—H3	108.5	Se2—C22—H22	108.5
C10—C5—C6	118.33 (18)	C28—C23—C24	118.42 (18)
C10—C5—C1	119.11 (17)	C28—C23—C19	119.78 (17)
C6—C5—C1	122.55 (17)	C24—C23—C19	121.81 (17)
C7—C6—C5	120.45 (19)	C25—C24—C23	120.44 (19)
C7—C6—H4	119.8	C25—C24—H23	119.8
C5—C6—H4	119.8	C23—C24—H23	119.8
C6—C7—C8	121.3 (2)	C26—C25—C24	121.5 (2)
C6—C7—H5	119.4	C26—C25—H24	119.3
C8—C7—H5	119.4	C24—C25—H24	119.3
C9—C8—C7	117.90 (19)	C25—C26—C27	117.98 (19)
C9—C8—C11	120.6 (2)	C25—C26—C29	120.9 (2)
C7—C8—C11	121.5 (2)	C27—C26—C29	121.1 (2)
C10—C9—C8	121.38 (19)	C28—C27—C26	121.3 (2)
C10—C9—H6	119.3	C28—C27—H25	119.4
C8—C9—H6	119.3	C26—C27—H25	119.4
C9—C10—C5	120.63 (19)	C27—C28—C23	120.38 (19)
C9—C10—H7	119.7	C27—C28—H26	119.8
C5—C10—H7	119.7	C23—C28—H26	119.8
C8—C11—H8	109.5	C26—C29—H27	109.5
C8—C11—H9	109.5	C26—C29—H28	109.5
H8—C11—H9	109.5	H27—C29—H28	109.5
C8—C11—H10	109.5	C26—C29—H29	109.5
H8—C11—H10	109.5	H27—C29—H29	109.5
H9—C11—H10	109.5	H28—C29—H29	109.5
C2—O1—H11	109.5	C20—O2—H30	109.5
C2—C12—H12	109.5	C20—C30—H31	109.5
C2—C12—H13	109.5	C20—C30—H32	109.5
H12—C12—H13	109.5	H31—C30—H32	109.5
C2—C12—H14	109.5	C20—C30—H33	109.5
H12—C12—H14	109.5	H31—C30—H33	109.5
H13—C12—H14	109.5	H32—C30—H33	109.5
C18—C13—C14	118.71 (18)	C36—C31—C32	118.65 (19)
C18—C13—C4	121.62 (17)	C36—C31—C22	121.96 (18)
C14—C13—C4	119.62 (18)	C32—C31—C22	119.33 (19)
C15—C14—C13	120.5 (2)	C31—C32—C33	120.5 (2)
C15—C14—H15	119.7	C31—C32—H34	119.8
C13—C14—H15	119.7	C33—C32—H34	119.8
C16—C15—C14	120.3 (2)	C34—C33—C32	120.2 (2)
C16—C15—H16	119.8	C34—C33—H35	119.9
C14—C15—H16	119.8	C32—C33—H35	119.9
C15—C16—C17	119.6 (2)	C33—C34—C35	120.0 (2)
C15—C16—H17	120.2	C33—C34—H36	120.0
C17—C16—H17	120.2	C35—C34—H36	120.0
C16—C17—C18	120.3 (2)	C34—C35—C36	120.0 (2)
C16—C17—H18	119.8	C34—C35—H37	120.0
C18—C17—H18	119.8	C36—C35—H37	120.0
C13—C18—C17	120.5 (2)	C35—C36—C31	120.6 (2)
C13—C18—H19	119.7	C35—C36—H38	119.7
C17—C18—H19	119.7	C31—C36—H38	119.7
C4—Se1—C1—N1	0.36 (19)	C22—Se2—C19—N2	−0.40 (18)
C4—Se1—C1—C5	178.76 (14)	C22—Se2—C19—C23	177.88 (13)
C5—C1—N1—C2	−179.15 (17)	C23—C19—N2—C20	178.71 (16)
Se1—C1—N1—C2	−0.8 (3)	Se2—C19—N2—C20	−3.1 (3)
C1—N1—C2—O1	−87.5 (2)	C19—N2—C20—O2	−84.0 (2)
C1—N1—C2—C12	153.10 (18)	C19—N2—C20—C30	156.55 (17)
C1—N1—C2—C3	31.5 (3)	C19—N2—C20—C21	34.7 (2)
O1—C2—C3—C4	52.2 (2)	O2—C20—C21—C22	51.2 (2)
N1—C2—C3—C4	−67.4 (2)	N2—C20—C21—C22	−68.0 (2)
C12—C2—C3—C4	173.21 (17)	C30—C20—C21—C22	171.90 (16)
C2—C3—C4—C13	−175.04 (16)	C20—C21—C22—C31	−179.74 (16)
C2—C3—C4—Se1	63.43 (18)	C20—C21—C22—Se2	60.40 (18)
C1—Se1—C4—C13	−153.72 (13)	C19—Se2—C22—C31	−151.95 (13)
C1—Se1—C4—C3	−29.43 (14)	C19—Se2—C22—C21	−26.42 (14)
N1—C1—C5—C10	31.1 (3)	N2—C19—C23—C28	39.3 (3)
Se1—C1—C5—C10	−147.47 (15)	Se2—C19—C23—C28	−139.10 (15)
N1—C1—C5—C6	−147.67 (19)	N2—C19—C23—C24	−140.36 (19)
Se1—C1—C5—C6	33.8 (2)	Se2—C19—C23—C24	41.2 (2)
C10—C5—C6—C7	−1.3 (3)	C28—C23—C24—C25	−1.8 (3)
C1—C5—C6—C7	177.47 (19)	C19—C23—C24—C25	177.86 (18)
C5—C6—C7—C8	0.2 (3)	C23—C24—C25—C26	0.8 (3)
C6—C7—C8—C9	1.1 (3)	C24—C25—C26—C27	1.1 (3)
C6—C7—C8—C11	−178.8 (2)	C24—C25—C26—C29	−176.20 (19)
C7—C8—C9—C10	−1.4 (3)	C25—C26—C27—C28	−1.9 (3)
C11—C8—C9—C10	178.6 (2)	C29—C26—C27—C28	175.34 (19)
C8—C9—C10—C5	0.3 (3)	C26—C27—C28—C23	0.9 (3)
C6—C5—C10—C9	1.1 (3)	C24—C23—C28—C27	1.0 (3)
C1—C5—C10—C9	−177.73 (18)	C19—C23—C28—C27	−178.72 (17)
C3—C4—C13—C18	−53.1 (3)	C21—C22—C31—C36	−48.0 (3)
Se1—C4—C13—C18	68.1 (2)	Se2—C22—C31—C36	73.1 (2)
C3—C4—C13—C14	124.3 (2)	C21—C22—C31—C32	134.69 (19)
Se1—C4—C13—C14	−114.51 (18)	Se2—C22—C31—C32	−104.19 (18)
C18—C13—C14—C15	1.6 (3)	C36—C31—C32—C33	0.2 (3)
C4—C13—C14—C15	−175.9 (2)	C22—C31—C32—C33	177.53 (19)
C13—C14—C15—C16	−0.5 (3)	C31—C32—C33—C34	−0.5 (3)
C14—C15—C16—C17	−0.8 (3)	C32—C33—C34—C35	0.6 (4)
C15—C16—C17—C18	0.8 (3)	C33—C34—C35—C36	−0.5 (3)
C14—C13—C18—C17	−1.5 (3)	C34—C35—C36—C31	0.2 (3)
C4—C13—C18—C17	175.9 (2)	C32—C31—C36—C35	0.0 (3)
C16—C17—C18—C13	0.3 (3)	C22—C31—C36—C35	−177.31 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···N1^i	0.84	2.04	2.872 (2)	173
O2—H30···N2^ii	0.84	2.06	2.893 (2)	175

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