2-(3-Cyano-4-methyl-5,5-diphenyl-5H-furan-2-yl-idene)malono-nitrile.

The title compound, C21H13N3O, crystallizes with two independent molecules with similar conformations per asymmetric unit. The dihydrofuran rings are essentially planar with maximum deviations of 0.017 (1) and 0.006 (1) Å for the O atoms. The dihedral angles between the di-hydro-furan ring and the attached phenyl rings are 79.90 (6) and 82.07 (6)° in one mol-ecule and 79.36 (6) and 72.26 (6)° in the other. In the crystal, the molecules are linked by weak C-H⋯π and C-H⋯N inter-actions similar to those in other closely related crystals. The replacement of appended methyl by phenyl groups has not significantly affected the dihydrofuran ring structure or the crystal packing interactions.

Related literature

For general background to NLO chromophores, see: Smith et al. (2006 ▶, 2010 ▶); Carey et al. (2002 ▶); Kay et al. (2004 ▶). For details of the synthesis, see: Anderson (2009 ▶). For related structures, see: Anderson (2009 ▶); Gainsford et al. (2011 ▶); Li et al. (2005 ▶); Liao et al. (2005 ▶). For geometric analysis of structures, see: Spek (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C21H13N3O

M = 323.34

Triclinic,

a = 9.2308 (3) Å

b = 12.5991 (4) Å

c = 14.3043 (4) Å

α = 89.954 (2)°

β = 89.052 (2)°

γ = 79.233 (2)°

V = 1634.07 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.36 × 0.32 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.651, T max = 0.746

45305 measured reflections

9930 independent reflections

7329 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.04

9930 reflections

453 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAIn class="Chemical">NT; 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, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020849/rz5081sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020849/rz5081Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020849/rz5081Isup3.cml

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

C21H13N3O	Z = 4
Mr = 323.34	F(000) = 672
Triclinic, P1	Dx = 1.314 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2308 (3) Å	Cell parameters from 9027 reflections
b = 12.5991 (4) Å	θ = 2.2–30.5°
c = 14.3043 (4) Å	µ = 0.08 mm−1
α = 89.954 (2)°	T = 123 K
β = 89.052 (2)°	Block, colourless
γ = 79.233 (2)°	0.36 × 0.32 × 0.29 mm
V = 1634.07 (9) Å3

Bruker APEXII CCD diffractometer	9930 independent reflections
Radiation source: fine-focus sealed tube	7329 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 8.333 pixels mm-1	θmax = 30.7°, θmin = 1.4°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
Tmin = 0.651, Tmax = 0.746	l = −20→20
45305 measured reflections

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) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3811P] where P = (Fo2 + 2Fc2)/3
9930 reflections	(Δ/σ)max < 0.001
453 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.24 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	0.34806 (9)	0.80434 (6)	0.09747 (5)	0.01913 (17)
N1	0.71127 (14)	0.64480 (10)	−0.12562 (9)	0.0387 (3)
N2	0.41086 (13)	0.95957 (10)	−0.09834 (8)	0.0315 (3)
N3	0.68541 (13)	0.46791 (10)	0.06030 (8)	0.0320 (3)
C1	0.62087 (14)	0.70061 (10)	−0.08395 (9)	0.0255 (3)
C2	0.50822 (13)	0.77028 (10)	−0.03197 (8)	0.0204 (2)
C3	0.45366 (13)	0.87575 (10)	−0.06807 (8)	0.0228 (2)
C4	0.40415 (12)	0.64052 (9)	0.17749 (8)	0.0194 (2)
C5	0.30203 (12)	0.74917 (9)	0.18178 (8)	0.0176 (2)
C6	0.45279 (12)	0.73785 (9)	0.04999 (8)	0.0183 (2)
C7	0.49044 (12)	0.63614 (9)	0.10052 (8)	0.0193 (2)
C8	0.60060 (13)	0.54476 (10)	0.07557 (8)	0.0225 (2)
C9	0.40783 (15)	0.55820 (10)	0.25144 (9)	0.0269 (3)
H9A	0.4637	0.4889	0.2288	0.032*
H9B	0.3069	0.5502	0.2677	0.032*
H9C	0.4553	0.5808	0.3069	0.032*
C10	0.14038 (12)	0.74436 (9)	0.16821 (8)	0.0188 (2)
C11	0.03222 (13)	0.83316 (10)	0.19229 (8)	0.0225 (2)
H11	0.0589	0.8940	0.2219	0.027*
C12	−0.11448 (14)	0.83266 (11)	0.17303 (9)	0.0278 (3)
H12	−0.1884	0.8930	0.1899	0.033*
C13	−0.15301 (14)	0.74430 (12)	0.12926 (9)	0.0301 (3)
H13	−0.2535	0.7441	0.1162	0.036*
C14	−0.04624 (15)	0.65645 (11)	0.10437 (9)	0.0288 (3)
H14	−0.0733	0.5963	0.0738	0.035*
C15	0.10062 (14)	0.65600 (10)	0.12400 (9)	0.0238 (2)
H15	0.1740	0.5953	0.1072	0.029*
C16	0.33659 (12)	0.80840 (9)	0.26874 (8)	0.0186 (2)
C17	0.45540 (13)	0.86160 (10)	0.26897 (9)	0.0226 (2)
H17	0.5119	0.8654	0.2134	0.027*
C18	0.49144 (15)	0.90922 (11)	0.35082 (9)	0.0287 (3)
H18	0.5728	0.9456	0.3512	0.034*
C19	0.40914 (17)	0.90379 (12)	0.43177 (9)	0.0337 (3)
H19	0.4334	0.9371	0.4875	0.040*
C20	0.29189 (17)	0.85014 (12)	0.43188 (9)	0.0329 (3)
H20	0.2352	0.8468	0.4875	0.040*
C21	0.25681 (15)	0.80120 (10)	0.35100 (8)	0.0255 (3)
H21	0.1778	0.7625	0.3517	0.031*
O1'	0.98981 (9)	0.20107 (6)	0.40488 (5)	0.01929 (17)
N1'	1.26942 (15)	0.36533 (11)	0.61930 (9)	0.0397 (3)
N2'	1.13037 (14)	0.05064 (10)	0.60095 (8)	0.0346 (3)
N3'	1.16038 (13)	0.53580 (9)	0.43102 (8)	0.0302 (2)
C1'	1.20774 (14)	0.30913 (11)	0.57926 (9)	0.0265 (3)
C2'	1.13161 (13)	0.23860 (10)	0.53017 (8)	0.0214 (2)
C3'	1.12990 (14)	0.13375 (10)	0.56895 (8)	0.0236 (2)
C4'	0.97057 (12)	0.35981 (9)	0.31831 (8)	0.0192 (2)
C5'	0.92300 (12)	0.25132 (9)	0.31831 (8)	0.0181 (2)
C6'	1.06105 (12)	0.26850 (9)	0.44854 (8)	0.0183 (2)
C7'	1.05045 (12)	0.36764 (9)	0.39479 (8)	0.0194 (2)
C8'	1.11373 (13)	0.45944 (10)	0.41679 (8)	0.0220 (2)
C9'	0.93503 (15)	0.43960 (10)	0.24239 (9)	0.0262 (3)
H9'A	0.9634	0.5077	0.2607	0.031*
H9'B	0.8289	0.4520	0.2309	0.031*
H9'C	0.9893	0.4120	0.1853	0.031*
C10'	0.75678 (12)	0.26066 (9)	0.33075 (8)	0.0187 (2)
C11'	0.68589 (13)	0.18118 (10)	0.29681 (9)	0.0231 (2)
H11'	0.7401	0.1214	0.2630	0.028*
C12'	0.53511 (14)	0.18933 (11)	0.31243 (9)	0.0276 (3)
H12'	0.4859	0.1359	0.2879	0.033*
C13'	0.45660 (14)	0.27472 (11)	0.36351 (10)	0.0290 (3)
H13'	0.3537	0.2798	0.3741	0.035*
C14'	0.52747 (14)	0.35269 (11)	0.39920 (10)	0.0291 (3)
H14'	0.4737	0.4106	0.4353	0.035*
C15'	0.67724 (14)	0.34638 (10)	0.38225 (9)	0.0241 (2)
H15'	0.7256	0.4007	0.4059	0.029*
C16'	0.99343 (13)	0.18644 (9)	0.23453 (8)	0.0189 (2)
C17'	1.13164 (13)	0.12020 (9)	0.24063 (9)	0.0217 (2)
H17'	1.1791	0.1096	0.2992	0.026*
C18'	1.19993 (14)	0.06974 (10)	0.16117 (9)	0.0262 (3)
H18'	1.2949	0.0254	0.1654	0.031*
C19'	1.13090 (16)	0.08335 (10)	0.07570 (9)	0.0288 (3)
H19'	1.1776	0.0478	0.0216	0.035*
C20'	0.99357 (15)	0.14899 (11)	0.06954 (9)	0.0287 (3)
H20'	0.9458	0.1584	0.0110	0.034*
C21'	0.92545 (14)	0.20087 (10)	0.14786 (8)	0.0252 (3)
H21'	0.8317	0.2467	0.1428	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0182 (4)	0.0211 (4)	0.0176 (4)	−0.0025 (3)	0.0024 (3)	0.0021 (3)
N1	0.0364 (7)	0.0400 (7)	0.0369 (7)	−0.0012 (6)	0.0125 (5)	−0.0044 (6)
N2	0.0309 (6)	0.0339 (6)	0.0282 (6)	−0.0025 (5)	0.0041 (5)	0.0049 (5)
N3	0.0288 (6)	0.0323 (6)	0.0317 (6)	0.0029 (5)	−0.0057 (5)	−0.0042 (5)
C1	0.0244 (6)	0.0287 (6)	0.0235 (6)	−0.0057 (5)	0.0027 (5)	0.0005 (5)
C2	0.0182 (5)	0.0246 (6)	0.0184 (5)	−0.0042 (4)	0.0005 (4)	−0.0005 (4)
C3	0.0206 (6)	0.0305 (6)	0.0177 (5)	−0.0060 (5)	0.0025 (4)	−0.0003 (5)
C4	0.0180 (5)	0.0202 (5)	0.0208 (5)	−0.0057 (4)	−0.0035 (4)	0.0002 (4)
C5	0.0172 (5)	0.0196 (5)	0.0160 (5)	−0.0039 (4)	0.0017 (4)	0.0020 (4)
C6	0.0153 (5)	0.0216 (5)	0.0184 (5)	−0.0045 (4)	−0.0021 (4)	−0.0018 (4)
C7	0.0171 (5)	0.0206 (5)	0.0204 (5)	−0.0039 (4)	−0.0027 (4)	−0.0016 (4)
C8	0.0193 (5)	0.0258 (6)	0.0225 (6)	−0.0045 (5)	−0.0035 (4)	−0.0022 (5)
C9	0.0306 (7)	0.0238 (6)	0.0258 (6)	−0.0040 (5)	−0.0005 (5)	0.0060 (5)
C10	0.0170 (5)	0.0241 (5)	0.0161 (5)	−0.0055 (4)	−0.0003 (4)	0.0021 (4)
C11	0.0203 (5)	0.0264 (6)	0.0211 (5)	−0.0049 (5)	0.0002 (4)	−0.0015 (5)
C12	0.0188 (6)	0.0365 (7)	0.0265 (6)	−0.0013 (5)	0.0000 (5)	0.0007 (5)
C13	0.0187 (6)	0.0440 (8)	0.0297 (6)	−0.0110 (5)	−0.0043 (5)	0.0040 (6)
C14	0.0281 (6)	0.0318 (7)	0.0301 (6)	−0.0146 (5)	−0.0055 (5)	0.0011 (5)
C15	0.0234 (6)	0.0238 (6)	0.0254 (6)	−0.0070 (5)	−0.0015 (5)	0.0000 (5)
C16	0.0180 (5)	0.0197 (5)	0.0180 (5)	−0.0032 (4)	−0.0026 (4)	0.0010 (4)
C17	0.0188 (5)	0.0234 (6)	0.0259 (6)	−0.0047 (4)	−0.0024 (5)	0.0033 (5)
C18	0.0287 (6)	0.0274 (6)	0.0330 (7)	−0.0121 (5)	−0.0109 (5)	0.0032 (5)
C19	0.0466 (8)	0.0355 (7)	0.0231 (6)	−0.0175 (6)	−0.0107 (6)	−0.0007 (5)
C20	0.0451 (8)	0.0385 (7)	0.0185 (6)	−0.0164 (6)	0.0006 (6)	0.0005 (5)
C21	0.0287 (6)	0.0306 (6)	0.0204 (5)	−0.0135 (5)	−0.0011 (5)	0.0015 (5)
O1'	0.0198 (4)	0.0208 (4)	0.0176 (4)	−0.0045 (3)	−0.0035 (3)	0.0023 (3)
N1'	0.0412 (7)	0.0389 (7)	0.0397 (7)	−0.0079 (6)	−0.0131 (6)	−0.0056 (6)
N2'	0.0397 (7)	0.0325 (6)	0.0303 (6)	−0.0033 (5)	−0.0062 (5)	0.0042 (5)
N3'	0.0302 (6)	0.0310 (6)	0.0312 (6)	−0.0109 (5)	0.0057 (5)	−0.0038 (5)
C1'	0.0250 (6)	0.0289 (6)	0.0243 (6)	−0.0013 (5)	−0.0044 (5)	−0.0013 (5)
C2'	0.0192 (5)	0.0246 (6)	0.0195 (5)	−0.0020 (4)	−0.0017 (4)	−0.0006 (4)
C3'	0.0229 (6)	0.0276 (6)	0.0184 (5)	−0.0002 (5)	−0.0034 (5)	−0.0010 (5)
C4'	0.0154 (5)	0.0209 (5)	0.0203 (5)	−0.0016 (4)	0.0033 (4)	0.0007 (4)
C5'	0.0175 (5)	0.0201 (5)	0.0158 (5)	−0.0011 (4)	−0.0022 (4)	0.0023 (4)
C6'	0.0141 (5)	0.0214 (5)	0.0188 (5)	−0.0019 (4)	0.0020 (4)	−0.0018 (4)
C7'	0.0161 (5)	0.0213 (5)	0.0208 (5)	−0.0036 (4)	0.0030 (4)	−0.0005 (4)
C8'	0.0188 (5)	0.0251 (6)	0.0219 (6)	−0.0042 (5)	0.0032 (4)	−0.0009 (5)
C9'	0.0293 (6)	0.0250 (6)	0.0241 (6)	−0.0046 (5)	−0.0004 (5)	0.0061 (5)
C10'	0.0167 (5)	0.0215 (5)	0.0172 (5)	−0.0015 (4)	−0.0001 (4)	0.0031 (4)
C11'	0.0214 (6)	0.0240 (6)	0.0234 (6)	−0.0030 (5)	0.0003 (5)	−0.0010 (5)
C12'	0.0221 (6)	0.0299 (6)	0.0325 (7)	−0.0087 (5)	−0.0021 (5)	0.0027 (5)
C13'	0.0177 (6)	0.0339 (7)	0.0344 (7)	−0.0025 (5)	0.0028 (5)	0.0059 (6)
C14'	0.0225 (6)	0.0284 (6)	0.0335 (7)	0.0019 (5)	0.0060 (5)	0.0001 (5)
C15'	0.0215 (6)	0.0234 (6)	0.0268 (6)	−0.0029 (5)	0.0013 (5)	−0.0013 (5)
C16'	0.0185 (5)	0.0196 (5)	0.0187 (5)	−0.0037 (4)	0.0012 (4)	0.0004 (4)
C17'	0.0196 (5)	0.0208 (5)	0.0244 (6)	−0.0029 (4)	0.0004 (4)	0.0020 (5)
C18'	0.0235 (6)	0.0215 (6)	0.0313 (6)	0.0008 (5)	0.0060 (5)	0.0021 (5)
C19'	0.0347 (7)	0.0257 (6)	0.0245 (6)	−0.0023 (5)	0.0103 (5)	−0.0019 (5)
C20'	0.0331 (7)	0.0337 (7)	0.0183 (5)	−0.0035 (6)	0.0014 (5)	0.0000 (5)
C21'	0.0220 (6)	0.0308 (6)	0.0208 (6)	0.0002 (5)	−0.0012 (5)	0.0022 (5)

O1—C6	1.3320 (14)	O1'—C6'	1.3295 (14)
O1—C5	1.4866 (13)	O1'—C5'	1.4808 (12)
N1—C1	1.1450 (17)	N1'—C1'	1.1469 (18)
N2—C3	1.1437 (16)	N2'—C3'	1.1417 (17)
N3—C8	1.1443 (16)	N3'—C8'	1.1448 (16)
C1—C2	1.4280 (18)	C1'—C2'	1.4239 (18)
C2—C6	1.3642 (16)	C2'—C6'	1.3647 (15)
C2—C3	1.4295 (16)	C2'—C3'	1.4351 (17)
C4—C7	1.3432 (17)	C4'—C7'	1.3432 (16)
C4—C9	1.4772 (16)	C4'—C9'	1.4779 (15)
C4—C5	1.5107 (16)	C4'—C5'	1.5118 (16)
C5—C16	1.5197 (16)	C5'—C16'	1.5180 (16)
C5—C10	1.5202 (16)	C5'—C10'	1.5243 (15)
C6—C7	1.4580 (15)	C6'—C7'	1.4547 (15)
C7—C8	1.4277 (17)	C7'—C8'	1.4273 (17)
C9—H9A	0.9800	C9'—H9'A	0.9800
C9—H9B	0.9800	C9'—H9'B	0.9800
C9—H9C	0.9800	C9'—H9'C	0.9800
C10—C15	1.3912 (17)	C10'—C11'	1.3866 (17)
C10—C11	1.3926 (17)	C10'—C15'	1.3911 (17)
C11—C12	1.3875 (17)	C11'—C12'	1.3907 (17)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.384 (2)	C12'—C13'	1.3816 (19)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.380 (2)	C13'—C14'	1.380 (2)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.3879 (17)	C14'—C15'	1.3872 (18)
C14—H14	0.9500	C14'—H14'	0.9500
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.3881 (16)	C16'—C17'	1.3919 (16)
C16—C21	1.3898 (17)	C16'—C21'	1.3952 (16)
C17—C18	1.3894 (18)	C17'—C18'	1.3861 (18)
C17—H17	0.9500	C17'—H17'	0.9500
C18—C19	1.383 (2)	C18'—C19'	1.3837 (19)
C18—H18	0.9500	C18'—H18'	0.9500
C19—C20	1.379 (2)	C19'—C20'	1.3822 (19)
C19—H19	0.9500	C19'—H19'	0.9500
C20—C21	1.3826 (18)	C20'—C21'	1.3792 (18)
C20—H20	0.9500	C20'—H20'	0.9500
C21—H21	0.9500	C21'—H21'	0.9500
C6—O1—C5	110.17 (8)	C6'—O1'—C5'	110.25 (8)
N1—C1—C2	179.94 (19)	N1'—C1'—C2'	179.47 (14)
C6—C2—C1	121.39 (11)	C6'—C2'—C1'	121.78 (11)
C6—C2—C3	120.28 (11)	C6'—C2'—C3'	120.02 (11)
C1—C2—C3	118.33 (11)	C1'—C2'—C3'	118.20 (10)
N2—C3—C2	178.90 (14)	N2'—C3'—C2'	178.76 (14)
C7—C4—C9	127.97 (11)	C7'—C4'—C9'	127.80 (11)
C7—C4—C5	109.10 (10)	C7'—C4'—C5'	109.09 (10)
C9—C4—C5	122.86 (11)	C9'—C4'—C5'	123.09 (10)
O1—C5—C4	102.37 (9)	O1'—C5'—C4'	102.35 (9)
O1—C5—C16	109.19 (9)	O1'—C5'—C16'	109.11 (8)
C4—C5—C16	108.53 (9)	C4'—C5'—C16'	108.89 (9)
O1—C5—C10	105.72 (8)	O1'—C5'—C10'	106.34 (8)
C4—C5—C10	114.22 (10)	C4'—C5'—C10'	112.82 (9)
C16—C5—C10	115.82 (10)	C16'—C5'—C10'	116.33 (10)
O1—C6—C2	120.36 (10)	O1'—C6'—C2'	120.27 (10)
O1—C6—C7	109.26 (10)	O1'—C6'—C7'	109.49 (9)
C2—C6—C7	130.38 (11)	C2'—C6'—C7'	130.22 (11)
C4—C7—C8	123.65 (11)	C4'—C7'—C8'	124.09 (11)
C4—C7—C6	109.02 (10)	C4'—C7'—C6'	108.81 (10)
C8—C7—C6	127.34 (11)	C8'—C7'—C6'	127.10 (10)
N3—C8—C7	175.48 (14)	N3'—C8'—C7'	176.62 (13)
C4—C9—H9A	109.5	C4'—C9'—H9'A	109.5
C4—C9—H9B	109.5	C4'—C9'—H9'B	109.5
H9A—C9—H9B	109.5	H9'A—C9'—H9'B	109.5
C4—C9—H9C	109.5	C4'—C9'—H9'C	109.5
H9A—C9—H9C	109.5	H9'A—C9'—H9'C	109.5
H9B—C9—H9C	109.5	H9'B—C9'—H9'C	109.5
C15—C10—C11	119.65 (11)	C11'—C10'—C15'	119.72 (11)
C15—C10—C5	120.37 (11)	C11'—C10'—C5'	120.81 (10)
C11—C10—C5	119.70 (11)	C15'—C10'—C5'	119.32 (11)
C12—C11—C10	119.95 (12)	C10'—C11'—C12'	119.71 (12)
C12—C11—H11	120.0	C10'—C11'—H11'	120.1
C10—C11—H11	120.0	C12'—C11'—H11'	120.1
C13—C12—C11	119.97 (12)	C13'—C12'—C11'	120.31 (12)
C13—C12—H12	120.0	C13'—C12'—H12'	119.8
C11—C12—H12	120.0	C11'—C12'—H12'	119.8
C14—C13—C12	120.39 (12)	C14'—C13'—C12'	120.11 (12)
C14—C13—H13	119.8	C14'—C13'—H13'	119.9
C12—C13—H13	119.8	C12'—C13'—H13'	119.9
C13—C14—C15	119.99 (12)	C13'—C14'—C15'	119.93 (12)
C13—C14—H14	120.0	C13'—C14'—H14'	120.0
C15—C14—H14	120.0	C15'—C14'—H14'	120.0
C14—C15—C10	120.03 (12)	C14'—C15'—C10'	120.18 (12)
C14—C15—H15	120.0	C14'—C15'—H15'	119.9
C10—C15—H15	120.0	C10'—C15'—H15'	119.9
C17—C16—C21	119.62 (11)	C17'—C16'—C21'	119.14 (11)
C17—C16—C5	120.49 (11)	C17'—C16'—C5'	120.97 (10)
C21—C16—C5	119.64 (10)	C21'—C16'—C5'	119.62 (10)
C16—C17—C18	119.77 (12)	C18'—C17'—C16'	119.95 (11)
C16—C17—H17	120.1	C18'—C17'—H17'	120.0
C18—C17—H17	120.1	C16'—C17'—H17'	120.0
C19—C18—C17	120.14 (12)	C19'—C18'—C17'	120.54 (11)
C19—C18—H18	119.9	C19'—C18'—H18'	119.7
C17—C18—H18	119.9	C17'—C18'—H18'	119.7
C20—C19—C18	120.17 (13)	C20'—C19'—C18'	119.58 (12)
C20—C19—H19	119.9	C20'—C19'—H19'	120.2
C18—C19—H19	119.9	C18'—C19'—H19'	120.2
C19—C20—C21	119.97 (13)	C21'—C20'—C19'	120.41 (12)
C19—C20—H20	120.0	C21'—C20'—H20'	119.8
C21—C20—H20	120.0	C19'—C20'—H20'	119.8
C20—C21—C16	120.30 (12)	C20'—C21'—C16'	120.36 (11)
C20—C21—H21	119.9	C20'—C21'—H21'	119.8
C16—C21—H21	119.9	C16'—C21'—H21'	119.8
C6—O1—C5—C4	2.74 (11)	C6'—O1'—C5'—C4'	1.01 (11)
C6—O1—C5—C16	117.63 (10)	C6'—O1'—C5'—C16'	116.26 (10)
C6—O1—C5—C10	−117.13 (10)	C6'—O1'—C5'—C10'	−117.54 (10)
C7—C4—C5—O1	−1.50 (12)	C7'—C4'—C5'—O1'	−0.64 (12)
C9—C4—C5—O1	175.57 (10)	C9'—C4'—C5'—O1'	177.60 (10)
C7—C4—C5—C16	−116.87 (11)	C7'—C4'—C5'—C16'	−116.05 (10)
C9—C4—C5—C16	60.21 (14)	C9'—C4'—C5'—C16'	62.19 (13)
C7—C4—C5—C10	112.25 (11)	C7'—C4'—C5'—C10'	113.21 (11)
C9—C4—C5—C10	−70.67 (14)	C9'—C4'—C5'—C10'	−68.54 (14)
C5—O1—C6—C2	177.73 (10)	C5'—O1'—C6'—C2'	−179.83 (10)
C5—O1—C6—C7	−2.95 (12)	C5'—O1'—C6'—C7'	−1.00 (12)
C1—C2—C6—O1	179.78 (11)	C1'—C2'—C6'—O1'	−179.38 (11)
C3—C2—C6—O1	−0.45 (17)	C3'—C2'—C6'—O1'	0.38 (17)
C1—C2—C6—C7	0.6 (2)	C1'—C2'—C6'—C7'	2.1 (2)
C3—C2—C6—C7	−179.61 (11)	C3'—C2'—C6'—C7'	−178.17 (12)
C9—C4—C7—C8	2.6 (2)	C9'—C4'—C7'—C8'	1.5 (2)
C5—C4—C7—C8	179.51 (11)	C5'—C4'—C7'—C8'	179.64 (11)
C9—C4—C7—C6	−177.01 (11)	C9'—C4'—C7'—C6'	−178.04 (11)
C5—C4—C7—C6	−0.12 (13)	C5'—C4'—C7'—C6'	0.10 (13)
O1—C6—C7—C4	1.95 (13)	O1'—C6'—C7'—C4'	0.57 (13)
C2—C6—C7—C4	−178.82 (12)	C2'—C6'—C7'—C4'	179.24 (12)
O1—C6—C7—C8	−177.67 (11)	O1'—C6'—C7'—C8'	−178.96 (11)
C2—C6—C7—C8	1.6 (2)	C2'—C6'—C7'—C8'	−0.3 (2)
O1—C5—C10—C15	90.54 (12)	O1'—C5'—C10'—C11'	−94.48 (12)
C4—C5—C10—C15	−21.21 (15)	C4'—C5'—C10'—C11'	154.11 (10)
C16—C5—C10—C15	−148.43 (10)	C16'—C5'—C10'—C11'	27.23 (14)
O1—C5—C10—C11	−83.48 (12)	O1'—C5'—C10'—C15'	81.20 (12)
C4—C5—C10—C11	164.77 (10)	C4'—C5'—C10'—C15'	−30.22 (14)
C16—C5—C10—C11	37.56 (14)	C16'—C5'—C10'—C15'	−157.09 (10)
C15—C10—C11—C12	0.68 (17)	C15'—C10'—C11'—C12'	1.69 (17)
C5—C10—C11—C12	174.74 (11)	C5'—C10'—C11'—C12'	177.34 (10)
C10—C11—C12—C13	−0.52 (18)	C10'—C11'—C12'—C13'	−1.61 (18)
C11—C12—C13—C14	−0.1 (2)	C11'—C12'—C13'—C14'	0.16 (19)
C12—C13—C14—C15	0.6 (2)	C12'—C13'—C14'—C15'	1.22 (19)
C13—C14—C15—C10	−0.41 (19)	C13'—C14'—C15'—C10'	−1.13 (19)
C11—C10—C15—C14	−0.22 (17)	C11'—C10'—C15'—C14'	−0.33 (17)
C5—C10—C15—C14	−174.24 (11)	C5'—C10'—C15'—C14'	−176.05 (11)
O1—C5—C16—C17	−30.62 (13)	O1'—C5'—C16'—C17'	−21.91 (15)
C4—C5—C16—C17	80.23 (12)	C4'—C5'—C16'—C17'	89.06 (12)
C10—C5—C16—C17	−149.77 (10)	C10'—C5'—C16'—C17'	−142.14 (11)
O1—C5—C16—C21	155.10 (10)	O1'—C5'—C16'—C21'	164.16 (10)
C4—C5—C16—C21	−94.05 (12)	C4'—C5'—C16'—C21'	−84.88 (13)
C10—C5—C16—C21	35.95 (15)	C10'—C5'—C16'—C21'	43.92 (15)
C21—C16—C17—C18	−1.44 (17)	C21'—C16'—C17'—C18'	0.08 (18)
C5—C16—C17—C18	−175.72 (10)	C5'—C16'—C17'—C18'	−173.88 (11)
C16—C17—C18—C19	−0.09 (19)	C16'—C17'—C18'—C19'	−0.94 (19)
C17—C18—C19—C20	0.7 (2)	C17'—C18'—C19'—C20'	0.8 (2)
C18—C19—C20—C21	0.3 (2)	C18'—C19'—C20'—C21'	0.1 (2)
C19—C20—C21—C16	−1.8 (2)	C19'—C20'—C21'—C16'	−1.0 (2)
C17—C16—C21—C20	2.41 (18)	C17'—C16'—C21'—C20'	0.86 (19)
C5—C16—C21—C20	176.74 (11)	C5'—C16'—C21'—C20'	174.90 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C20′—H20′···Cg1i	0.95	2.69	3.4041 (14)	133
C9—H9B···N3′	0.98	2.70	3.4560 (14)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 phenyl ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20′—H20′⋯Cg1i	0.95	2.69	3.4041 (14)	133
C9—H9B⋯N3′	0.98	2.70	3.4560 (14)	134

Symmetry code: (i) .