1-(3-Phenyl-isoquinolin-1-yl)hydrazine.

The title compound, C(15)H(13)N(3), contains two independent mol-ecules in the asymmetric unit. The isoquinoline moiety and phenyl rings form dihedral angles of 4.38 (2) and 10.14 (3)° in the two independent mol-ecules. The crystal packing is stabilized by N-H⋯N mol-ecular dimers formed across a center of symmetry.

Related literature

For general background to hydrazine compounds, see: Broadhurst et al. (2001 ▶); Behrens (1999 ▶); Broadhurst (1991 ▶); Chao et al. (1999 ▶); Kametani (1968 ▶). For related crystal structures, see: Yang et al. (2008 ▶); Choudhury & Guru Row (2006 ▶); Choudhury et al. (2002 ▶); Hathwar et al. (2008 ▶). For bond-length data, see: Allen et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H13N3

M = 235.28

Triclinic,

a = 6.672 (2) Å

b = 13.825 (4) Å

c = 14.934 (5) Å

α = 63.836 (5)°

β = 86.895 (6)°

γ = 82.106 (5)°

V = 1224.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 290 (2) K

0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.953, T max = 0.996

12381 measured reflections

4546 independent reflections

2926 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 1.02

4546 reflections

429 parameters

All H-atom parameters refined

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042062/cs2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042062/cs2101Isup2.hkl

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

C15H13N3	Z = 4
Mr = 235.28	F(000) = 496
Triclinic, P1	Dx = 1.276 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.672 (2) Å	Cell parameters from 832 reflections
b = 13.825 (4) Å	θ = 1.7–25.3°
c = 14.934 (5) Å	µ = 0.08 mm−1
α = 63.836 (5)°	T = 290 K
β = 86.895 (6)°	Needle, colourless
γ = 82.106 (5)°	0.15 × 0.12 × 0.05 mm
V = 1224.5 (7) Å3

Bruker SMART CCD area-detector diffractometer	4546 independent reflections
Radiation source: fine-focus sealed tube	2926 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.953, Tmax = 0.996	k = −16→16
12381 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
4546 reflections	(Δ/σ)max < 0.001
429 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.91992 (19)	0.17183 (10)	0.48294 (10)	0.0386 (3)
N2	0.6714 (2)	0.05976 (11)	0.52799 (11)	0.0433 (4)
N3	0.7300 (2)	0.02645 (15)	0.45200 (14)	0.0471 (4)
N1'	0.4205 (2)	0.13567 (10)	0.03997 (10)	0.0391 (3)
N2'	0.1689 (2)	0.07962 (11)	−0.01722 (11)	0.0466 (4)
N3'	0.2325 (2)	−0.03027 (12)	0.04958 (15)	0.0495 (4)
C1	0.7552 (2)	0.14107 (12)	0.53468 (12)	0.0366 (4)
C2	1.0076 (2)	0.25388 (13)	0.48758 (12)	0.0406 (4)
C3	0.9290 (3)	0.30370 (15)	0.54472 (14)	0.0529 (5)
C4	0.6656 (4)	0.32080 (18)	0.66201 (16)	0.0718 (7)
C5	0.4979 (4)	0.28801 (19)	0.71627 (17)	0.0768 (7)
C6	0.4084 (4)	0.20448 (17)	0.71345 (16)	0.0666 (6)
C7	0.4885 (3)	0.15463 (16)	0.65585 (14)	0.0515 (5)
C8	0.6624 (2)	0.18705 (12)	0.59912 (12)	0.0395 (4)
C9	0.7543 (3)	0.27114 (14)	0.60246 (13)	0.0482 (5)
C10	1.1910 (2)	0.28398 (13)	0.42535 (12)	0.0431 (4)
C11	1.2553 (3)	0.23496 (16)	0.36341 (13)	0.0523 (5)
C12	1.4255 (3)	0.26016 (18)	0.30579 (15)	0.0639 (6)
C13	1.5362 (4)	0.33508 (19)	0.30874 (17)	0.0679 (6)
C14	1.4761 (3)	0.38509 (18)	0.36893 (17)	0.0655 (6)
C15	1.3048 (3)	0.36044 (16)	0.42676 (15)	0.0561 (5)
C1'	0.2527 (2)	0.16171 (13)	−0.01268 (12)	0.0385 (4)
C2'	0.5085 (2)	0.21556 (13)	0.04790 (12)	0.0406 (4)
C3'	0.4252 (3)	0.32116 (15)	0.00313 (14)	0.0531 (5)
C4'	0.1531 (4)	0.45988 (17)	−0.10239 (18)	0.0780 (7)
C5'	−0.0202 (4)	0.48553 (19)	−0.15637 (19)	0.0876 (8)
C6'	−0.1088 (4)	0.40594 (18)	−0.16610 (16)	0.0735 (7)
C7'	−0.0217 (3)	0.30071 (16)	−0.12234 (14)	0.0547 (5)
C8'	0.1569 (3)	0.27129 (13)	−0.06543 (12)	0.0411 (4)
C9'	0.2471 (3)	0.35185 (14)	−0.05511 (13)	0.0502 (5)
C10'	0.6945 (2)	0.17691 (14)	0.11012 (12)	0.0412 (4)
C11'	0.7519 (3)	0.06689 (16)	0.16619 (14)	0.0525 (5)
C12'	0.9251 (3)	0.02867 (18)	0.22499 (15)	0.0599 (5)
C13'	1.0450 (3)	0.09997 (19)	0.22820 (15)	0.0587 (5)
C14'	0.9911 (3)	0.2093 (2)	0.17264 (15)	0.0608 (6)
C15'	0.8188 (3)	0.24744 (17)	0.11461 (15)	0.0532 (5)
H2N	0.542 (3)	0.0483 (14)	0.5454 (13)	0.060 (6)*
H3	0.992 (3)	0.3609 (14)	0.5471 (12)	0.056 (5)*
H3A	0.843 (3)	−0.0248 (16)	0.4726 (14)	0.075 (7)*
H3B	0.761 (3)	0.0880 (17)	0.3956 (15)	0.078 (7)*
H4	0.733 (3)	0.3797 (16)	0.6607 (14)	0.082 (7)*
H5	0.438 (3)	0.3227 (17)	0.7544 (16)	0.094 (7)*
H2'N	0.038 (3)	0.0910 (13)	−0.0365 (12)	0.053 (5)*
H6	0.286 (3)	0.1827 (16)	0.7500 (15)	0.084 (7)*
H3'A	0.269 (3)	−0.0320 (14)	0.1126 (14)	0.065 (6)*
H3'B	0.341 (3)	−0.0536 (16)	0.0238 (15)	0.076 (7)*
H7	0.423 (3)	0.1003 (14)	0.6516 (12)	0.055 (5)*
H11	1.172 (3)	0.1806 (14)	0.3645 (13)	0.062 (5)*
H12	1.470 (3)	0.2194 (16)	0.2639 (15)	0.090 (7)*
H13	1.658 (3)	0.3473 (17)	0.2734 (16)	0.095 (8)*
H14	1.549 (3)	0.4356 (15)	0.3753 (13)	0.069 (6)*
H15	1.263 (3)	0.3971 (14)	0.4688 (13)	0.059 (6)*
H3'	0.492 (3)	0.3731 (15)	0.0110 (13)	0.064 (6)*
H4'	0.219 (3)	0.5136 (17)	−0.0959 (14)	0.082 (7)*
H5'	−0.082 (4)	0.5558 (19)	−0.1851 (17)	0.102 (8)*
H6'	−0.234 (3)	0.4247 (16)	−0.2025 (15)	0.080 (7)*
H7'	−0.081 (3)	0.2459 (15)	−0.1303 (13)	0.065 (6)*
H11'	0.661 (3)	0.0177 (14)	0.1642 (12)	0.057 (5)*
H12'	0.964 (3)	−0.0520 (18)	0.2615 (15)	0.092 (7)*
H13'	1.164 (3)	0.0723 (15)	0.2692 (14)	0.070 (6)*
H14'	1.073 (3)	0.2590 (16)	0.1730 (14)	0.078 (6)*
H15'	0.786 (3)	0.3249 (15)	0.0727 (14)	0.069 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0333 (8)	0.0399 (8)	0.0440 (8)	−0.0050 (6)	−0.0015 (6)	−0.0194 (7)
N2	0.0385 (9)	0.0477 (9)	0.0538 (9)	−0.0105 (7)	0.0057 (7)	−0.0306 (8)
N3	0.0416 (9)	0.0510 (10)	0.0609 (11)	−0.0049 (8)	0.0013 (8)	−0.0358 (9)
N1'	0.0349 (8)	0.0393 (8)	0.0494 (8)	−0.0077 (6)	0.0027 (7)	−0.0245 (7)
N2'	0.0365 (9)	0.0386 (9)	0.0688 (11)	−0.0028 (7)	−0.0065 (8)	−0.0271 (8)
N3'	0.0420 (10)	0.0382 (9)	0.0720 (12)	−0.0014 (7)	−0.0050 (9)	−0.0281 (9)
C1	0.0341 (9)	0.0347 (9)	0.0398 (9)	−0.0008 (7)	−0.0057 (8)	−0.0155 (8)
C2	0.0388 (10)	0.0401 (10)	0.0416 (10)	−0.0052 (8)	−0.0054 (8)	−0.0161 (8)
C3	0.0572 (12)	0.0539 (12)	0.0606 (12)	−0.0214 (10)	0.0080 (10)	−0.0337 (10)
C4	0.0929 (18)	0.0715 (15)	0.0772 (15)	−0.0321 (13)	0.0289 (13)	−0.0532 (13)
C5	0.0979 (19)	0.0770 (16)	0.0769 (16)	−0.0248 (14)	0.0364 (14)	−0.0532 (14)
C6	0.0735 (15)	0.0659 (14)	0.0659 (14)	−0.0203 (12)	0.0312 (12)	−0.0341 (12)
C7	0.0539 (12)	0.0495 (11)	0.0541 (12)	−0.0111 (10)	0.0095 (9)	−0.0250 (10)
C8	0.0416 (10)	0.0374 (9)	0.0368 (9)	−0.0013 (8)	−0.0019 (8)	−0.0145 (8)
C9	0.0549 (12)	0.0462 (11)	0.0496 (11)	−0.0100 (9)	0.0041 (9)	−0.0259 (9)
C10	0.0393 (10)	0.0408 (10)	0.0415 (10)	−0.0048 (8)	−0.0055 (8)	−0.0106 (8)
C11	0.0525 (12)	0.0569 (12)	0.0458 (11)	−0.0127 (10)	0.0048 (9)	−0.0198 (10)
C12	0.0592 (14)	0.0723 (15)	0.0525 (13)	−0.0113 (11)	0.0097 (10)	−0.0205 (12)
C13	0.0505 (14)	0.0723 (15)	0.0578 (14)	−0.0092 (12)	0.0081 (11)	−0.0081 (12)
C14	0.0508 (13)	0.0575 (13)	0.0733 (15)	−0.0191 (11)	−0.0029 (12)	−0.0115 (12)
C15	0.0510 (12)	0.0508 (12)	0.0652 (14)	−0.0133 (10)	0.0005 (10)	−0.0223 (11)
C1'	0.0354 (10)	0.0413 (10)	0.0454 (10)	−0.0068 (8)	0.0065 (8)	−0.0252 (8)
C2'	0.0408 (10)	0.0411 (10)	0.0447 (10)	−0.0115 (8)	0.0077 (8)	−0.0223 (8)
C3'	0.0611 (13)	0.0420 (11)	0.0600 (12)	−0.0146 (10)	−0.0037 (10)	−0.0230 (10)
C4'	0.1021 (19)	0.0388 (12)	0.0861 (17)	−0.0059 (12)	−0.0263 (15)	−0.0189 (12)
C5'	0.115 (2)	0.0430 (14)	0.0886 (18)	0.0131 (14)	−0.0384 (16)	−0.0160 (13)
C6'	0.0877 (18)	0.0566 (14)	0.0677 (15)	0.0104 (13)	−0.0303 (13)	−0.0215 (12)
C7'	0.0602 (13)	0.0500 (12)	0.0537 (12)	−0.0013 (10)	−0.0095 (10)	−0.0231 (10)
C8'	0.0450 (10)	0.0400 (10)	0.0381 (10)	−0.0051 (8)	0.0030 (8)	−0.0174 (8)
C9'	0.0620 (13)	0.0359 (10)	0.0505 (11)	−0.0080 (9)	−0.0019 (10)	−0.0161 (9)
C10'	0.0406 (10)	0.0492 (11)	0.0424 (10)	−0.0116 (8)	0.0061 (8)	−0.0269 (9)
C11'	0.0573 (13)	0.0514 (12)	0.0513 (12)	−0.0153 (10)	−0.0051 (10)	−0.0217 (10)
C12'	0.0654 (14)	0.0609 (14)	0.0523 (12)	−0.0064 (11)	−0.0107 (10)	−0.0232 (11)
C13'	0.0533 (13)	0.0777 (16)	0.0502 (12)	−0.0078 (12)	−0.0060 (10)	−0.0322 (12)
C14'	0.0571 (13)	0.0779 (16)	0.0612 (13)	−0.0257 (12)	−0.0016 (11)	−0.0380 (13)
C15'	0.0556 (12)	0.0543 (13)	0.0575 (13)	−0.0162 (10)	−0.0002 (10)	−0.0288 (11)

N1—C1	1.3163 (19)	C12—C13	1.369 (3)
N1—C2	1.3748 (19)	C12—H12	1.02 (2)
N2—C1	1.3652 (19)	C13—C14	1.371 (3)
N2—N3	1.420 (2)	C13—H13	0.94 (2)
N2—H2N	0.904 (18)	C14—C15	1.381 (3)
N3—H3A	0.920 (19)	C14—H14	0.94 (2)
N3—H3B	0.93 (2)	C15—H15	0.976 (17)
N1'—C1'	1.317 (2)	C1'—C8'	1.435 (2)
N1'—C2'	1.3712 (19)	C2'—C3'	1.358 (2)
N2'—C1'	1.360 (2)	C2'—C10'	1.481 (2)
N2'—N3'	1.420 (2)	C3'—C9'	1.413 (3)
N2'—H2'N	0.903 (18)	C3'—H3'	0.946 (18)
N3'—H3'A	0.976 (19)	C4'—C5'	1.360 (3)
N3'—H3'B	0.89 (2)	C4'—C9'	1.408 (3)
C1—C8	1.442 (2)	C4'—H4'	0.96 (2)
C2—C3	1.359 (2)	C5'—C6'	1.382 (3)
C2—C10	1.487 (2)	C5'—H5'	0.92 (2)
C3—C9	1.414 (2)	C6'—C7'	1.361 (3)
C3—H3	0.959 (17)	C6'—H6'	0.96 (2)
C4—C5	1.353 (3)	C7'—C8'	1.407 (2)
C4—C9	1.408 (2)	C7'—H7'	0.955 (18)
C4—H4	0.98 (2)	C8'—C9'	1.404 (2)
C5—C6	1.388 (3)	C10'—C11'	1.383 (2)
C5—H5	0.94 (2)	C10'—C15'	1.389 (2)
C6—C7	1.368 (3)	C11'—C12'	1.386 (3)
C6—H6	0.96 (2)	C11'—H11'	0.983 (17)
C7—C8	1.402 (2)	C12'—C13'	1.370 (3)
C7—H7	0.945 (17)	C12'—H12'	1.00 (2)
C8—C9	1.407 (2)	C13'—C14'	1.370 (3)
C10—C11	1.389 (2)	C13'—H13'	0.95 (2)
C10—C15	1.391 (2)	C14'—C15'	1.374 (3)
C11—C12	1.375 (3)	C14'—H14'	0.94 (2)
C11—H11	0.988 (18)	C15'—H15'	0.972 (18)
C1—N1—C2	119.22 (14)	C14—C13—H13	120.8 (13)
C1—N2—N3	121.14 (14)	C13—C14—C15	120.6 (2)
C1—N2—H2N	122.1 (11)	C13—C14—H14	123.3 (12)
N3—N2—H2N	109.5 (11)	C15—C14—H14	116.1 (12)
N2—N3—H3A	109.6 (12)	C14—C15—C10	120.6 (2)
N2—N3—H3B	107.2 (12)	C14—C15—H15	119.7 (11)
H3A—N3—H3B	109.9 (18)	C10—C15—H15	119.8 (11)
C1'—N1'—C2'	119.52 (14)	N1'—C1'—N2'	117.49 (15)
C1'—N2'—N3'	120.66 (15)	N1'—C1'—C8'	123.38 (14)
C1'—N2'—H2'N	119.4 (11)	N2'—C1'—C8'	119.13 (15)
N3'—N2'—H2'N	112.8 (11)	C3'—C2'—N1'	121.27 (16)
N2'—N3'—H3'A	107.7 (11)	C3'—C2'—C10'	123.79 (16)
N2'—N3'—H3'B	108.0 (13)	N1'—C2'—C10'	114.93 (15)
H3'A—N3'—H3'B	109.2 (17)	C2'—C3'—C9'	120.53 (17)
N1—C1—N2	117.71 (15)	C2'—C3'—H3'	117.9 (11)
N1—C1—C8	123.47 (14)	C9'—C3'—H3'	121.5 (11)
N2—C1—C8	118.81 (15)	C5'—C4'—C9'	121.0 (2)
C3—C2—N1	121.64 (16)	C5'—C4'—H4'	122.4 (12)
C3—C2—C10	123.14 (16)	C9'—C4'—H4'	116.6 (12)
N1—C2—C10	115.22 (15)	C4'—C5'—C6'	120.7 (2)
C2—C3—C9	120.43 (17)	C4'—C5'—H5'	120.1 (15)
C2—C3—H3	120.7 (10)	C6'—C5'—H5'	119.2 (15)
C9—C3—H3	118.9 (10)	C7'—C6'—C5'	120.1 (2)
C5—C4—C9	121.3 (2)	C7'—C6'—H6'	119.9 (12)
C5—C4—H4	123.4 (12)	C5'—C6'—H6'	120.0 (12)
C9—C4—H4	115.3 (12)	C6'—C7'—C8'	120.6 (2)
C4—C5—C6	120.2 (2)	C6'—C7'—H7'	120.2 (11)
C4—C5—H5	120.7 (14)	C8'—C7'—H7'	119.2 (11)
C6—C5—H5	119.0 (14)	C9'—C8'—C7'	119.44 (17)
C7—C6—C5	120.5 (2)	C9'—C8'—C1'	116.33 (15)
C7—C6—H6	119.1 (12)	C7'—C8'—C1'	124.19 (16)
C5—C6—H6	120.4 (12)	C8'—C9'—C4'	118.12 (19)
C6—C7—C8	120.42 (19)	C8'—C9'—C3'	118.93 (16)
C6—C7—H7	120.1 (10)	C4'—C9'—C3'	122.94 (18)
C8—C7—H7	119.4 (10)	C11'—C10'—C15'	117.18 (17)
C7—C8—C9	119.24 (16)	C11'—C10'—C2'	120.30 (16)
C7—C8—C1	124.44 (16)	C15'—C10'—C2'	122.51 (17)
C9—C8—C1	116.31 (15)	C10'—C11'—C12'	121.42 (18)
C8—C9—C4	118.37 (18)	C10'—C11'—H11'	116.7 (10)
C8—C9—C3	118.91 (16)	C12'—C11'—H11'	121.9 (10)
C4—C9—C3	122.71 (18)	C13'—C12'—C11'	120.2 (2)
C11—C10—C15	117.55 (18)	C13'—C12'—H12'	121.5 (12)
C11—C10—C2	120.17 (16)	C11'—C12'—H12'	118.2 (12)
C15—C10—C2	122.27 (17)	C12'—C13'—C14'	119.1 (2)
C12—C11—C10	121.6 (2)	C12'—C13'—H13'	119.1 (12)
C12—C11—H11	122.8 (10)	C14'—C13'—H13'	121.8 (12)
C10—C11—H11	115.6 (10)	C13'—C14'—C15'	120.8 (2)
C13—C12—C11	120.0 (2)	C13'—C14'—H14'	120.1 (12)
C13—C12—H12	121.3 (12)	C15'—C14'—H14'	119.1 (12)
C11—C12—H12	118.6 (12)	C14'—C15'—C10'	121.3 (2)
C12—C13—C14	119.8 (2)	C14'—C15'—H15'	119.9 (11)
C12—C13—H13	119.3 (13)	C10'—C15'—H15'	118.8 (11)
C2—N1—C1—N2	179.67 (14)	C2'—N1'—C1'—N2'	−179.00 (14)
C2—N1—C1—C8	−1.7 (2)	C2'—N1'—C1'—C8'	1.6 (2)
N3—N2—C1—N1	−14.0 (2)	N3'—N2'—C1'—N1'	14.0 (2)
N3—N2—C1—C8	167.31 (15)	N3'—N2'—C1'—C8'	−166.61 (15)
C1—N1—C2—C3	0.4 (2)	C1'—N1'—C2'—C3'	0.5 (2)
C1—N1—C2—C10	−179.08 (13)	C1'—N1'—C2'—C10'	179.06 (14)
N1—C2—C3—C9	0.7 (3)	N1'—C2'—C3'—C9'	−1.5 (3)
C10—C2—C3—C9	−179.86 (15)	C10'—C2'—C3'—C9'	−179.91 (15)
C9—C4—C5—C6	−0.6 (4)	C9'—C4'—C5'—C6'	0.1 (4)
C4—C5—C6—C7	−0.1 (4)	C4'—C5'—C6'—C7'	−0.7 (4)
C5—C6—C7—C8	0.2 (3)	C5'—C6'—C7'—C8'	1.1 (3)
C6—C7—C8—C9	0.3 (3)	C6'—C7'—C8'—C9'	−0.9 (3)
C6—C7—C8—C1	−178.62 (17)	C6'—C7'—C8'—C1'	176.68 (18)
N1—C1—C8—C7	−179.17 (15)	N1'—C1'—C8'—C9'	−2.6 (2)
N2—C1—C8—C7	−0.6 (2)	N2'—C1'—C8'—C9'	177.99 (15)
N1—C1—C8—C9	1.9 (2)	N1'—C1'—C8'—C7'	179.72 (16)
N2—C1—C8—C9	−179.52 (14)	N2'—C1'—C8'—C7'	0.3 (2)
C7—C8—C9—C4	−0.9 (3)	C7'—C8'—C9'—C4'	0.3 (3)
C1—C8—C9—C4	178.12 (17)	C1'—C8'—C9'—C4'	−177.49 (17)
C7—C8—C9—C3	−179.72 (16)	C7'—C8'—C9'—C3'	179.33 (17)
C1—C8—C9—C3	−0.7 (2)	C1'—C8'—C9'—C3'	1.6 (2)
C5—C4—C9—C8	1.0 (3)	C5'—C4'—C9'—C8'	0.1 (3)
C5—C4—C9—C3	179.8 (2)	C5'—C4'—C9'—C3'	−178.9 (2)
C2—C3—C9—C8	−0.5 (3)	C2'—C3'—C9'—C8'	0.4 (3)
C2—C3—C9—C4	−179.28 (18)	C2'—C3'—C9'—C4'	179.37 (19)
C3—C2—C10—C11	−175.55 (17)	C3'—C2'—C10'—C11'	169.50 (17)
N1—C2—C10—C11	3.9 (2)	N1'—C2'—C10'—C11'	−9.0 (2)
C3—C2—C10—C15	4.8 (3)	C3'—C2'—C10'—C15'	−11.0 (3)
N1—C2—C10—C15	−175.73 (15)	N1'—C2'—C10'—C15'	170.47 (15)
C15—C10—C11—C12	0.4 (3)	C15'—C10'—C11'—C12'	0.5 (3)
C2—C10—C11—C12	−179.27 (16)	C2'—C10'—C11'—C12'	180.00 (16)
C10—C11—C12—C13	0.1 (3)	C10'—C11'—C12'—C13'	−0.4 (3)
C11—C12—C13—C14	−0.3 (3)	C11'—C12'—C13'—C14'	0.1 (3)
C12—C13—C14—C15	0.1 (3)	C12'—C13'—C14'—C15'	0.3 (3)
C13—C14—C15—C10	0.4 (3)	C13'—C14'—C15'—C10'	−0.2 (3)
C11—C10—C15—C14	−0.6 (3)	C11'—C10'—C15'—C14'	−0.2 (3)
C2—C10—C15—C14	179.05 (16)	C2'—C10'—C15'—C14'	−179.68 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2'—H2'N···N3'i	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N···N3ii	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3'—H3'B···N1'iii	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A···N1iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2′—H2′N⋯N3′i	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N⋯N3ii	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3′—H3′B⋯N1′iii	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A⋯N1iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)

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