2-{3-Cyano-5,5-dimethyl-4-[4-(piperidin-1-yl)buta-1,3-dien-yl]-2,5-dihydro-furan-2-yl-idene}malononitrile.

The title compound, C(19)H(20)N(4)O, crystallizes as twinned crystals containing two independent mol-ecules which pack into a three-dimensional matrix via several C-H⋯N(cyano) inter-actions, with a C⋯N range of 3.324 (8)-3.568 (8) Å and C-H⋯N angles in the range 147-166°.

Related literature

For general background, see: Kay et al. (2004 ▶); Gainsford et al. (2007 ▶, 2008 ▶). For related structures, see: Bock et al. (1996 ▶); Marder et al. (1993 ▶); Reck & Dahne (2006 ▶); Allen (2002 ▶).

Experimental

Crystal data

C19H20N4O

M = 320.39

Monoclinic,

a = 15.094 (4) Å

b = 18.994 (5) Å

c = 13.332 (4) Å

β = 116.193 (8)°

V = 3429.7 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 119 (2) K

0.35 × 0.25 × 0.09 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.733, T max = 1.0 (expected range = 0.728–0.993)

18712 measured reflections

11128 independent reflections

5766 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.203

S = 1.02

11128 reflections

424 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT and SADABS (Sheldrick, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000548/gg3141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000548/gg3141Isup2.hkl

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

C19H20N4O	F000 = 1360
Mr = 320.39	Dx = 1.241 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4176 reflections
a = 15.094 (4) Å	θ = 2.7–30.2º
b = 18.994 (5) Å	µ = 0.08 mm−1
c = 13.332 (4) Å	T = 119 (2) K
β = 116.193 (8)º	Plate, red
V = 3429.7 (16) Å3	0.35 × 0.25 × 0.09 mm
Z = 8

Bruker–Nonius APEXII CCD area-detector diffractometer	11128 independent reflections
Radiation source: fine-focus sealed tube	5766 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.088
Detector resolution: 8.192 pixels mm-1	θmax = 25.0º
T = 119(2) K	θmin = 2.0º
/f and /w scans	h = −16→17
Absorption correction: multi-scan(Blessing, 1995)	k = −22→22
Tmin = 0.733, Tmax = 1.0	l = −15→15
18712 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.079	w = 1/[σ2(Fo2) + (0.041P)2 + 5.943P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.203	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.46 e Å−3
11128 reflections	Δρmin = −0.36 e Å−3
424 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)
Secondary atom site location: difference Fourier map

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. An extinction parameter was refined. Data above 2θ 50° were excluded on the basis of low intensity/error ratio. A total of 477 reflections were either not recorded or affected by the backstop within this θ limit (of 6035 expected). A further 13 reflections (and their Friedel opposites) were omitted from the refinement on the basis of being clearly outliers (with Fo<<Fc).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	0.7393 (3)	0.8303 (2)	0.4515 (3)	0.0343 (10)
N1	0.9567 (4)	0.7590 (3)	0.2970 (5)	0.0422 (15)
N2	0.8344 (4)	0.9570 (3)	0.3440 (4)	0.0489 (15)
N3	0.8724 (4)	0.6091 (3)	0.4162 (5)	0.0473 (15)
N4	0.5250 (3)	0.5399 (2)	0.7252 (4)	0.0326 (12)
C1	0.9063 (4)	0.7849 (3)	0.3282 (5)	0.0356 (16)
C2	0.8470 (4)	0.8229 (3)	0.3707 (5)	0.0321 (14)
C3	0.8397 (4)	0.8966 (4)	0.3552 (5)	0.0362 (15)
C4	0.7276 (4)	0.7135 (3)	0.5029 (5)	0.0289 (15)
C5	0.6857 (4)	0.7869 (3)	0.4989 (5)	0.0311 (15)
C6	0.7962 (4)	0.7888 (3)	0.4209 (5)	0.0305 (14)
C7	0.7908 (4)	0.7191 (3)	0.4492 (5)	0.0283 (14)*
C8	0.5770 (4)	0.7903 (3)	0.4147 (5)	0.0395 (16)
H8A	0.5545	0.8394	0.4055	0.059*
H8B	0.5378	0.7621	0.4420	0.059*
H8C	0.5690	0.7718	0.3426	0.059*
C9	0.7073 (4)	0.8205 (3)	0.6121 (5)	0.0400 (17)
H9A	0.6905	0.8707	0.6015	0.060*
H9B	0.7776	0.8151	0.6630	0.060*
H9C	0.6677	0.7971	0.6440	0.060*
C10	0.8375 (4)	0.6601 (3)	0.4304 (5)	0.0336 (15)
C11	0.7080 (4)	0.6540 (3)	0.5476 (5)	0.0344 (16)
H11	0.7436	0.6126	0.5486	0.041*
C12	0.6398 (4)	0.6493 (3)	0.5920 (4)	0.0297 (14)
H12	0.6046	0.6906	0.5925	0.036*
C13	0.6206 (4)	0.5883 (3)	0.6352 (5)	0.0323 (15)
H13	0.6557	0.5462	0.6387	0.039*
C14	0.5483 (4)	0.5901 (3)	0.6736 (5)	0.0362 (16)
H14	0.5117	0.6327	0.6610	0.043*
C15	0.4434 (4)	0.5482 (3)	0.7556 (5)	0.0389 (16)
H15A	0.4120	0.5948	0.7305	0.047*
H15B	0.4690	0.5458	0.8379	0.047*
C16	0.3684 (4)	0.4911 (3)	0.7020 (5)	0.0438 (17)*
H16A	0.3393	0.4959	0.6197	0.053*
H16B	0.3147	0.4958	0.7250	0.053*
C17	0.4162 (4)	0.4197 (3)	0.7361 (5)	0.0448 (17)
H17A	0.3667	0.3824	0.6982	0.054*
H17B	0.4412	0.4135	0.8178	0.054*
C18	0.5018 (4)	0.4130 (3)	0.7040 (6)	0.0430 (17)*
H18A	0.5355	0.3673	0.7307	0.052*
H18B	0.4756	0.4143	0.6216	0.052*
C19	0.5750 (4)	0.4721 (3)	0.7545 (5)	0.0391 (16)
H19A	0.6084	0.4669	0.8368	0.047*
H19B	0.6259	0.4697	0.7267	0.047*
O1'	0.2394 (3)	0.8340 (2)	0.2535 (3)	0.0340 (10)
N1'	0.4636 (4)	0.7639 (3)	0.6209 (5)	0.0443 (15)
N2'	0.3455 (4)	0.9652 (3)	0.4508 (4)	0.0480 (15)
N3'	0.3582 (4)	0.6149 (3)	0.4407 (4)	0.0443 (15)
N4'	0.0597 (3)	0.5220 (2)	−0.2095 (4)	0.0313 (12)
C1'	0.4113 (4)	0.7928 (3)	0.5417 (5)	0.0347 (15)
C2'	0.3478 (4)	0.8300 (3)	0.4436 (5)	0.0288 (14)
C3'	0.3455 (4)	0.9041 (4)	0.4475 (5)	0.0334 (15)
C4'	0.2259 (4)	0.7152 (3)	0.1981 (5)	0.0269 (14)
C5'	0.1910 (4)	0.7881 (3)	0.1521 (5)	0.0320 (15)
C6'	0.2942 (4)	0.7932 (3)	0.3443 (5)	0.0311 (15)
C7'	0.2857 (4)	0.7224 (3)	0.3153 (5)	0.0295 (15)
C8'	0.0811 (4)	0.7979 (3)	0.1116 (5)	0.0465 (18)
H8'A	0.0653	0.8482	0.1026	0.070*
H8'B	0.0613	0.7778	0.1663	0.070*
H8'C	0.0456	0.7740	0.0396	0.070*
C9'	0.2278 (4)	0.8151 (3)	0.0713 (5)	0.0422 (17)
H9'A	0.2170	0.8660	0.0622	0.063*
H9'B	0.1918	0.7918	−0.0011	0.063*
H9'C	0.2984	0.8050	0.1002	0.063*
C10'	0.3282 (4)	0.6651 (3)	0.3876 (5)	0.0315 (15)
C11'	0.2043 (4)	0.6539 (3)	0.1390 (5)	0.0303 (14)
H11'	0.2299	0.6119	0.1804	0.036*
C12'	0.1479 (4)	0.6464 (3)	0.0229 (5)	0.0296 (14)
H12'	0.1188	0.6872	−0.0203	0.035*
C13'	0.1330 (4)	0.5823 (3)	−0.0312 (5)	0.0318 (15)
H13'	0.1608	0.5407	0.0103	0.038*
C14'	0.0770 (4)	0.5789 (3)	−0.1468 (5)	0.0330 (15)
H14'	0.0486	0.6217	−0.1841	0.040*
C15'	−0.0091 (4)	0.5216 (3)	−0.3290 (5)	0.0425 (18)
H15C	0.0259	0.5050	−0.3723	0.051*
H15D	−0.0324	0.5702	−0.3534	0.051*
C16'	−0.0964 (4)	0.4748 (3)	−0.3530 (5)	0.0440 (17)
H16C	−0.1387	0.4728	−0.4346	0.053*
H16D	−0.1362	0.4944	−0.3172	0.053*
C17'	−0.0618 (4)	0.4010 (3)	−0.3085 (5)	0.0444 (18)
H17C	−0.0300	0.3789	−0.3516	0.053*
H17D	−0.1194	0.3718	−0.3183	0.053*
C18'	0.0114 (4)	0.4035 (3)	−0.1846 (5)	0.0419 (18)
H18C	−0.0224	0.4209	−0.1406	0.050*
H18D	0.0362	0.3554	−0.1583	0.050*
C19'	0.0967 (4)	0.4509 (3)	−0.1666 (5)	0.0374 (15)
H19C	0.1422	0.4535	−0.0858	0.045*
H19D	0.1337	0.4317	−0.2060	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.041 (3)	0.032 (2)	0.036 (3)	0.000 (2)	0.023 (2)	0.003 (2)
N1	0.037 (3)	0.047 (4)	0.047 (4)	0.001 (3)	0.023 (3)	0.002 (3)
N2	0.066 (4)	0.047 (4)	0.037 (4)	−0.002 (3)	0.026 (3)	−0.004 (3)
N3	0.051 (4)	0.047 (4)	0.053 (4)	0.002 (3)	0.031 (3)	0.005 (3)
N4	0.028 (3)	0.036 (3)	0.034 (3)	0.000 (3)	0.014 (2)	0.002 (3)
C1	0.024 (4)	0.039 (4)	0.035 (4)	−0.001 (3)	0.005 (3)	0.002 (3)
C2	0.033 (3)	0.034 (4)	0.032 (4)	−0.004 (3)	0.016 (3)	−0.002 (3)
C3	0.036 (4)	0.044 (4)	0.028 (4)	−0.006 (4)	0.014 (3)	−0.004 (3)
C4	0.024 (3)	0.030 (4)	0.030 (4)	−0.008 (3)	0.010 (3)	−0.004 (3)
C5	0.037 (4)	0.029 (4)	0.035 (4)	−0.007 (3)	0.023 (3)	−0.002 (3)
C6	0.025 (3)	0.043 (4)	0.024 (3)	−0.001 (3)	0.012 (3)	−0.001 (3)
C8	0.033 (4)	0.047 (4)	0.040 (4)	0.005 (3)	0.017 (3)	0.005 (3)
C9	0.053 (4)	0.044 (4)	0.027 (4)	−0.004 (3)	0.021 (3)	−0.010 (3)
C10	0.030 (4)	0.042 (4)	0.027 (3)	−0.003 (3)	0.011 (3)	0.008 (3)
C11	0.028 (3)	0.041 (4)	0.034 (4)	−0.006 (3)	0.014 (3)	0.000 (3)
C12	0.023 (3)	0.035 (4)	0.027 (3)	−0.004 (3)	0.007 (3)	0.000 (3)
C13	0.030 (4)	0.031 (4)	0.035 (4)	−0.003 (3)	0.013 (3)	−0.001 (3)
C14	0.029 (4)	0.039 (4)	0.036 (4)	−0.006 (3)	0.010 (3)	0.002 (3)
C15	0.036 (4)	0.043 (4)	0.045 (4)	−0.007 (3)	0.024 (3)	0.001 (3)
C17	0.043 (4)	0.046 (4)	0.047 (4)	−0.013 (4)	0.020 (3)	−0.005 (4)
C19	0.034 (4)	0.047 (4)	0.039 (4)	0.008 (3)	0.018 (3)	0.010 (3)
O1'	0.038 (3)	0.037 (3)	0.022 (2)	0.001 (2)	0.0086 (19)	−0.005 (2)
N1'	0.045 (4)	0.045 (4)	0.034 (4)	0.003 (3)	0.010 (3)	−0.007 (3)
N2'	0.060 (4)	0.049 (4)	0.037 (4)	−0.004 (3)	0.023 (3)	−0.004 (3)
N3'	0.042 (3)	0.051 (4)	0.035 (3)	0.006 (3)	0.012 (3)	0.003 (3)
N4'	0.035 (3)	0.024 (3)	0.028 (3)	−0.001 (2)	0.008 (2)	−0.003 (2)
C1'	0.027 (4)	0.043 (4)	0.029 (4)	−0.004 (3)	0.007 (3)	−0.008 (3)
C2'	0.022 (3)	0.034 (4)	0.028 (3)	−0.001 (3)	0.009 (3)	−0.001 (3)
C3'	0.035 (4)	0.047 (4)	0.020 (3)	−0.004 (4)	0.014 (3)	−0.006 (3)
C4'	0.020 (3)	0.033 (4)	0.027 (3)	−0.001 (3)	0.009 (2)	−0.005 (3)
C5'	0.031 (4)	0.043 (4)	0.015 (3)	−0.005 (3)	0.004 (2)	−0.006 (3)
C6'	0.020 (3)	0.046 (4)	0.024 (3)	−0.001 (3)	0.008 (3)	−0.003 (3)
C7'	0.021 (3)	0.035 (4)	0.028 (4)	0.002 (3)	0.007 (3)	0.000 (3)
C8'	0.046 (4)	0.055 (4)	0.034 (4)	0.009 (4)	0.013 (3)	−0.001 (3)
C9'	0.059 (4)	0.039 (4)	0.030 (4)	0.002 (3)	0.020 (3)	0.006 (3)
C10'	0.026 (4)	0.037 (4)	0.030 (4)	−0.001 (3)	0.010 (3)	−0.006 (3)
C11'	0.024 (3)	0.036 (4)	0.026 (3)	0.004 (3)	0.007 (3)	0.000 (3)
C12'	0.031 (3)	0.028 (3)	0.031 (4)	0.003 (3)	0.015 (3)	0.000 (3)
C13'	0.026 (3)	0.038 (4)	0.028 (4)	−0.001 (3)	0.009 (3)	−0.002 (3)
C14'	0.034 (4)	0.028 (4)	0.036 (4)	−0.002 (3)	0.015 (3)	−0.006 (3)
C15'	0.051 (4)	0.045 (4)	0.021 (3)	0.008 (4)	0.007 (3)	0.000 (3)
C16'	0.036 (4)	0.054 (5)	0.035 (4)	0.000 (4)	0.009 (3)	−0.004 (3)
C17'	0.034 (4)	0.052 (5)	0.043 (4)	−0.007 (4)	0.014 (3)	−0.010 (3)
C18'	0.050 (4)	0.041 (4)	0.034 (4)	−0.005 (3)	0.017 (3)	−0.005 (3)
C19'	0.037 (4)	0.033 (4)	0.037 (4)	0.010 (3)	0.012 (3)	0.000 (3)

O1—C6	1.355 (6)	O1'—C6'	1.365 (6)
O1—C5	1.478 (6)	O1'—C5'	1.500 (6)
N1—C1	1.128 (7)	N1'—C1'	1.141 (7)
N2—C3	1.156 (7)	N2'—C3'	1.161 (7)
N3—C10	1.157 (7)	N3'—C10'	1.154 (7)
N4—C14	1.310 (7)	N4'—C14'	1.320 (6)
N4—C19	1.458 (6)	N4'—C15'	1.468 (6)
N4—C15	1.466 (7)	N4'—C19'	1.477 (6)
C1—C2	1.446 (8)	C1'—C2'	1.422 (8)
C2—C6	1.381 (8)	C2'—C6'	1.396 (7)
C2—C3	1.412 (8)	C2'—C3'	1.410 (8)
C4—C11	1.370 (7)	C4'—C11'	1.362 (7)
C4—C7	1.426 (8)	C4'—C7'	1.425 (7)
C4—C5	1.523 (8)	C4'—C5'	1.511 (7)
C5—C8	1.527 (7)	C5'—C9'	1.503 (8)
C5—C9	1.534 (8)	C5'—C8'	1.512 (7)
C6—C7	1.390 (7)	C6'—C7'	1.390 (7)
C7—C10	1.404 (8)	C7'—C10'	1.407 (8)
C8—H8A	0.9800	C8'—H8'A	0.9800
C8—H8B	0.9800	C8'—H8'B	0.9800
C8—H8C	0.9800	C8'—H8'C	0.9800
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
C11—C12	1.398 (7)	C11'—C12'	1.405 (8)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.380 (7)	C12'—C13'	1.382 (7)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.396 (8)	C13'—C14'	1.395 (7)
C13—H13	0.9500	C13'—H13'	0.9500
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.501 (7)	C15'—C16'	1.503 (8)
C15—H15A	0.9900	C15'—H15C	0.9900
C15—H15B	0.9900	C15'—H15D	0.9900
C16—C17	1.509 (7)	C16'—C17'	1.522 (8)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
C17—C18	1.536 (8)	C17'—C18'	1.530 (7)
C17—H17A	0.9900	C17'—H17C	0.9900
C17—H17B	0.9900	C17'—H17D	0.9900
C18—C19	1.508 (7)	C18'—C19'	1.501 (7)
C18—H18A	0.9900	C18'—H18C	0.9900
C18—H18B	0.9900	C18'—H18D	0.9900
C19—H19A	0.9900	C19'—H19C	0.9900
C19—H19B	0.9900	C19'—H19D	0.9900
C6—O1—C5	110.2 (4)	C6'—O1'—C5'	109.4 (4)
C14—N4—C19	123.9 (5)	C14'—N4'—C15'	122.6 (5)
C14—N4—C15	121.3 (5)	C14'—N4'—C19'	124.6 (5)
C19—N4—C15	114.8 (5)	C15'—N4'—C19'	112.4 (4)
N1—C1—C2	175.4 (7)	N1'—C1'—C2'	178.8 (7)
C6—C2—C3	120.7 (6)	C6'—C2'—C3'	121.4 (5)
C6—C2—C1	121.9 (5)	C6'—C2'—C1'	119.8 (5)
C3—C2—C1	117.4 (6)	C3'—C2'—C1'	118.7 (5)
N2—C3—C2	179.1 (8)	N2'—C3'—C2'	178.7 (7)
C11—C4—C7	126.9 (6)	C11'—C4'—C7'	126.2 (5)
C11—C4—C5	127.2 (5)	C11'—C4'—C5'	126.6 (5)
C7—C4—C5	105.9 (5)	C7'—C4'—C5'	107.2 (5)
O1—C5—C4	103.2 (4)	O1'—C5'—C9'	105.1 (4)
O1—C5—C8	106.0 (5)	O1'—C5'—C4'	102.9 (4)
C4—C5—C8	111.1 (5)	C9'—C5'—C4'	115.5 (5)
O1—C5—C9	105.7 (4)	O1'—C5'—C8'	105.8 (5)
C4—C5—C9	116.2 (5)	C9'—C5'—C8'	113.3 (5)
C8—C5—C9	113.5 (5)	C4'—C5'—C8'	112.8 (5)
O1—C6—C2	115.8 (5)	O1'—C6'—C7'	110.9 (5)
O1—C6—C7	110.5 (5)	O1'—C6'—C2'	115.4 (5)
C2—C6—C7	133.7 (6)	C7'—C6'—C2'	133.7 (6)
C6—C7—C10	128.1 (5)	C6'—C7'—C10'	126.9 (5)
C6—C7—C4	109.9 (5)	C6'—C7'—C4'	109.5 (5)
C10—C7—C4	122.0 (5)	C10'—C7'—C4'	123.6 (5)
C5—C8—H8A	109.5	C5'—C8'—H8'A	109.5
C5—C8—H8B	109.5	C5'—C8'—H8'B	109.5
H8A—C8—H8B	109.5	H8'A—C8'—H8'B	109.5
C5—C8—H8C	109.5	C5'—C8'—H8'C	109.5
H8A—C8—H8C	109.5	H8'A—C8'—H8'C	109.5
H8B—C8—H8C	109.5	H8'B—C8'—H8'C	109.5
C5—C9—H9A	109.5	C5'—C9'—H9'A	109.5
C5—C9—H9B	109.5	C5'—C9'—H9'B	109.5
H9A—C9—H9B	109.5	H9'A—C9'—H9'B	109.5
C5—C9—H9C	109.5	C5'—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
N3—C10—C7	176.2 (6)	N3'—C10'—C7'	174.9 (6)
C4—C11—C12	125.3 (6)	C4'—C11'—C12'	126.7 (6)
C4—C11—H11	117.3	C4'—C11'—H11'	116.7
C12—C11—H11	117.3	C12'—C11'—H11'	116.7
C13—C12—C11	124.1 (6)	C13'—C12'—C11'	122.9 (6)
C13—C12—H12	118.0	C13'—C12'—H12'	118.5
C11—C12—H12	118.0	C11'—C12'—H12'	118.5
C12—C13—C14	118.4 (6)	C12'—C13'—C14'	119.8 (6)
C12—C13—H13	120.8	C12'—C13'—H13'	120.1
C14—C13—H13	120.8	C14'—C13'—H13'	120.1
N4—C14—C13	127.5 (6)	N4'—C14'—C13'	126.3 (6)
N4—C14—H14	116.3	N4'—C14'—H14'	116.9
C13—C14—H14	116.3	C13'—C14'—H14'	116.9
N4—C15—C16	109.8 (5)	N4'—C15'—C16'	111.6 (5)
N4—C15—H15A	109.7	N4'—C15'—H15C	109.3
C16—C15—H15A	109.7	C16'—C15'—H15C	109.3
N4—C15—H15B	109.7	N4'—C15'—H15D	109.3
C16—C15—H15B	109.7	C16'—C15'—H15D	109.3
H15A—C15—H15B	108.2	H15C—C15'—H15D	108.0
C15—C16—C17	110.3 (5)	C15'—C16'—C17'	110.2 (5)
C15—C16—H16A	109.6	C15'—C16'—H16C	109.6
C17—C16—H16A	109.6	C17'—C16'—H16C	109.6
C15—C16—H16B	109.6	C15'—C16'—H16D	109.6
C17—C16—H16B	109.6	C17'—C16'—H16D	109.6
H16A—C16—H16B	108.1	H16C—C16'—H16D	108.1
C16—C17—C18	109.8 (5)	C16'—C17'—C18'	110.6 (5)
C16—C17—H17A	109.7	C16'—C17'—H17C	109.5
C18—C17—H17A	109.7	C18'—C17'—H17C	109.5
C16—C17—H17B	109.7	C16'—C17'—H17D	109.5
C18—C17—H17B	109.7	C18'—C17'—H17D	109.5
H17A—C17—H17B	108.2	H17C—C17'—H17D	108.1
C19—C18—C17	110.8 (5)	C19'—C18'—C17'	110.6 (5)
C19—C18—H18A	109.5	C19'—C18'—H18C	109.5
C17—C18—H18A	109.5	C17'—C18'—H18C	109.5
C19—C18—H18B	109.5	C19'—C18'—H18D	109.5
C17—C18—H18B	109.5	C17'—C18'—H18D	109.5
H18A—C18—H18B	108.1	H18C—C18'—H18D	108.1
N4—C19—C18	110.3 (5)	N4'—C19'—C18'	109.6 (4)
N4—C19—H19A	109.6	N4'—C19'—H19C	109.8
C18—C19—H19A	109.6	C18'—C19'—H19C	109.8
N4—C19—H19B	109.6	N4'—C19'—H19D	109.8
C18—C19—H19B	109.6	C18'—C19'—H19D	109.8
H19A—C19—H19B	108.1	H19C—C19'—H19D	108.2
C6—O1—C5—C4	5.6 (5)	C6'—O1'—C5'—C9'	−121.2 (5)
C6—O1—C5—C8	−111.2 (5)	C6'—O1'—C5'—C4'	0.1 (6)
C6—O1—C5—C9	128.1 (5)	C6'—O1'—C5'—C8'	118.7 (5)
C11—C4—C5—O1	174.9 (5)	C11'—C4'—C5'—O1'	−178.6 (5)
C7—C4—C5—O1	−5.7 (6)	C7'—C4'—C5'—O1'	1.6 (6)
C11—C4—C5—C8	−71.9 (7)	C11'—C4'—C5'—C9'	−64.7 (8)
C7—C4—C5—C8	107.4 (5)	C7'—C4'—C5'—C9'	115.5 (5)
C11—C4—C5—C9	59.8 (7)	C11'—C4'—C5'—C8'	67.9 (8)
C7—C4—C5—C9	−120.8 (5)	C7'—C4'—C5'—C8'	−112.0 (5)
C5—O1—C6—C2	177.3 (5)	C5'—O1'—C6'—C7'	−1.7 (7)
C5—O1—C6—C7	−3.3 (6)	C5'—O1'—C6'—C2'	176.7 (5)
C3—C2—C6—O1	0.9 (8)	C3'—C2'—C6'—O1'	−0.9 (8)
C1—C2—C6—O1	−176.6 (5)	C1'—C2'—C6'—O1'	−176.6 (5)
C3—C2—C6—C7	−178.2 (6)	C3'—C2'—C6'—C7'	177.0 (7)
C1—C2—C6—C7	4.3 (11)	C1'—C2'—C6'—C7'	1.3 (11)
O1—C6—C7—C10	179.1 (5)	O1'—C6'—C7'—C10'	−177.2 (5)
C2—C6—C7—C10	−1.7 (11)	C2'—C6'—C7'—C10'	4.8 (11)
O1—C6—C7—C4	−0.6 (7)	O1'—C6'—C7'—C4'	2.8 (7)
C2—C6—C7—C4	178.5 (6)	C2'—C6'—C7'—C4'	−175.2 (6)
C11—C4—C7—C6	−176.5 (5)	C11'—C4'—C7'—C6'	177.5 (6)
C5—C4—C7—C6	4.1 (7)	C5'—C4'—C7'—C6'	−2.7 (6)
C11—C4—C7—C10	3.8 (10)	C11'—C4'—C7'—C10'	−2.5 (10)
C5—C4—C7—C10	−175.6 (5)	C5'—C4'—C7'—C10'	177.3 (5)
C7—C4—C11—C12	−174.8 (6)	C7'—C4'—C11'—C12'	−177.9 (6)
C5—C4—C11—C12	4.4 (10)	C5'—C4'—C11'—C12'	2.3 (10)
C4—C11—C12—C13	179.1 (5)	C4'—C11'—C12'—C13'	177.1 (6)
C11—C12—C13—C14	−177.9 (6)	C11'—C12'—C13'—C14'	−179.4 (5)
C19—N4—C14—C13	1.9 (10)	C15'—N4'—C14'—C13'	173.0 (6)
C15—N4—C14—C13	−176.8 (6)	C19'—N4'—C14'—C13'	0.6 (10)
C12—C13—C14—N4	−174.1 (5)	C12'—C13'—C14'—N4'	177.6 (5)
C14—N4—C15—C16	121.5 (6)	C14'—N4'—C15'—C16'	−115.0 (6)
C19—N4—C15—C16	−57.3 (6)	C19'—N4'—C15'—C16'	58.3 (7)
N4—C15—C16—C17	57.2 (7)	N4'—C15'—C16'—C17'	−55.0 (7)
C15—C16—C17—C18	−57.4 (7)	C15'—C16'—C17'—C18'	53.9 (7)
C16—C17—C18—C19	55.7 (7)	C16'—C17'—C18'—C19'	−55.8 (7)
C14—N4—C19—C18	−123.2 (6)	C14'—N4'—C19'—C18'	114.3 (6)
C15—N4—C19—C18	55.5 (7)	C15'—N4'—C19'—C18'	−58.9 (7)
C17—C18—C19—N4	−53.5 (7)	C17'—C18'—C19'—N4'	57.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C13'—H13'···N2i	0.95	2.49	3.324 (8)	147
C14—H14···N1'	0.95	2.58	3.498 (8)	161
C14'—H14'···N1ii	0.95	2.61	3.484 (8)	153
C16'—H16D···N2ii	0.99	2.55	3.477 (8)	156
C19—H19A···N2'iii	0.99	2.60	3.568 (8)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13′—H13′⋯N2i	0.95	2.49	3.324 (8)	147
C14—H14⋯N1′	0.95	2.58	3.498 (8)	161
C14′—H14′⋯N1ii	0.95	2.61	3.484 (8)	153
C16′—H16D⋯N2ii	0.99	2.55	3.477 (8)	156
C19—H19A⋯N2′iii	0.99	2.60	3.568 (8)	166

Symmetry codes: (i) ; (ii) ; (iii) .