3-Amino-5,5-di-phenyl-imidazolidine-2,4-dione.

The title compound, C15H13N3O2, crystallizes with two independent mol-ecules in the asymmetric unit, which differ considerably in the dihedral angles made between the phenyl groups and the five-membered rings [47.19 (8) and 61.16 (9)° in one mol-ecule and 55.04 (10) and 55.00 (8)° in the other]. In the crystal, N-H⋯O hydrogen bonds generate columnar units having approximate fourfold rotational symmetry about axes parallel to b.

Related literature

For the biological properties of hydantoins, see: El-Deeb et al. (2010 ▶); Rajic et al. (2006 ▶); Carmi et al. (2006 ▶); Sergent et al. (2008 ▶). For the preparation of the title compound, see: Kiec-Kononowicz et al. (1984 ▶). For related crystal structures, see: Delgado et al. (2007 ▶); Roszak & Weaver (1998 ▶); Kashif et al. (2008 ▶); Coquerel et al. (1993 ▶); SethuSankar et al. (2002 ▶); Eknoian et al. (1999 ▶); Ciechanowicz-Rutkowska et al. (1994 ▶).

Experimental

Crystal data

C15H13N3O2

M = 267.28

Monoclinic,

a = 20.1565 (7) Å

b = 6.1651 (2) Å

c = 20.3250 (7) Å

β = 97.781 (2)°

V = 2502.47 (15) Å3

Z = 8

Cu Kα radiation

μ = 0.79 mm−1

T = 100 K

0.22 × 0.07 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.84, T max = 0.96

32772 measured reflections

4560 independent reflections

3185 reflections with I > 2σ(I)

R int = 0.105

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.111

S = 1.08

4560 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002487/sj5389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002487/sj5389Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002487/sj5389Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H13N3O2	F(000) = 1120
Mr = 267.28	Dx = 1.419 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 20.1565 (7) Å	Cell parameters from 9869 reflections
b = 6.1651 (2) Å	θ = 2.9–68.2°
c = 20.3250 (7) Å	µ = 0.79 mm−1
β = 97.781 (2)°	T = 100 K
V = 2502.47 (15) Å3	Needle, clear colourless
Z = 8	0.22 × 0.07 × 0.05 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4560 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3185 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.105
Detector resolution: 10.4167 pixels mm-1	θmax = 68.4°, θmin = 2.9°
ω scans	h = −23→24
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −7→7
Tmin = 0.84, Tmax = 0.96	l = −24→24
32772 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)] = 0.054	Hydrogen site location: mixed
wR(F2) = 0.111	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.021P)2 + 2.7033P] where P = (Fo2 + 2Fc2)/3
4560 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.22 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
O1	0.78438 (9)	0.0796 (3)	0.48058 (9)	0.0231 (4)
O2	0.90255 (9)	0.6421 (3)	0.40602 (9)	0.0254 (4)
N1	0.80979 (10)	0.6347 (3)	0.46106 (10)	0.0201 (5)
H1	0.8013	0.7785	0.4655	0.024*
N2	0.85417 (10)	0.3212 (3)	0.43843 (10)	0.0198 (5)
N3	0.90346 (11)	0.1794 (4)	0.42044 (11)	0.0255 (5)
H3A	0.9247	0.1205	0.4586	0.031*
H3B	0.8834	0.0767	0.3923	0.031*
C1	0.77157 (13)	0.4751 (4)	0.49361 (12)	0.0189 (6)
C2	0.80275 (13)	0.2652 (4)	0.47094 (12)	0.0194 (6)
C3	0.86045 (13)	0.5491 (4)	0.43294 (12)	0.0205 (6)
C4	0.69599 (13)	0.4923 (4)	0.47123 (12)	0.0191 (6)
C5	0.65335 (13)	0.3213 (5)	0.48164 (13)	0.0255 (6)
H5	0.6714	0.1904	0.5012	0.031*
C6	0.58517 (14)	0.3413 (5)	0.46371 (14)	0.0303 (7)
H6C	0.5566	0.2234	0.4708	0.036*
C7	0.55780 (15)	0.5314 (5)	0.43552 (14)	0.0316 (7)
H7	0.5108	0.5442	0.4231	0.038*
C8	0.59973 (14)	0.7018 (5)	0.42579 (14)	0.0299 (7)
H8	0.5814	0.8336	0.4071	0.036*
C9	0.66835 (14)	0.6820 (4)	0.44302 (13)	0.0246 (6)
H9	0.6968	0.7998	0.4354	0.030*
C10	0.78600 (12)	0.4917 (4)	0.56998 (13)	0.0201 (6)
C11	0.80444 (13)	0.6912 (4)	0.59968 (13)	0.0255 (6)
H11	0.8090	0.8148	0.5727	0.031*
C12	0.81613 (14)	0.7099 (5)	0.66814 (14)	0.0309 (7)
H12	0.8284	0.8466	0.6877	0.037*
C13	0.81028 (14)	0.5327 (5)	0.70839 (14)	0.0294 (7)
H13	0.8190	0.5462	0.7553	0.035*
C14	0.79153 (14)	0.3359 (5)	0.67955 (14)	0.0291 (7)
H14	0.7872	0.2131	0.7069	0.035*
C15	0.77886 (14)	0.3151 (5)	0.61077 (13)	0.0259 (6)
H15	0.7652	0.1789	0.5916	0.031*
O3	0.93849 (10)	0.0679 (3)	0.56241 (9)	0.0279 (5)
O4	0.99521 (9)	0.6386 (3)	0.70282 (9)	0.0235 (4)
N4	0.97628 (11)	0.0837 (3)	0.67430 (10)	0.0218 (5)
H4	0.9832	−0.0606	0.6816	0.026*
N5	0.96189 (10)	0.3934 (3)	0.62039 (10)	0.0195 (5)
N6	0.95376 (11)	0.5316 (3)	0.56462 (10)	0.0240 (5)
H6A	0.9316	0.6529	0.5750	0.029*
H6B	0.9960	0.5739	0.5595	0.029*
C16	0.99947 (13)	0.2460 (4)	0.72474 (12)	0.0200 (6)
C17	0.98609 (12)	0.4523 (4)	0.68303 (12)	0.0181 (6)
C18	0.95735 (13)	0.1661 (4)	0.61355 (13)	0.0206 (6)
C19	1.07440 (13)	0.2216 (4)	0.75053 (12)	0.0195 (6)
C20	1.10590 (14)	0.0225 (4)	0.74733 (14)	0.0264 (6)
H20	1.0815	−0.0973	0.7270	0.032*
C21	1.17274 (14)	−0.0036 (5)	0.77354 (15)	0.0303 (7)
H21	1.1935	−0.1411	0.7710	0.036*
C22	1.20901 (14)	0.1669 (5)	0.80305 (13)	0.0283 (7)
H22	1.2547	0.1484	0.8209	0.034*
C23	1.17813 (14)	0.3665 (5)	0.80648 (14)	0.0307 (7)
H23	1.2029	0.4858	0.8266	0.037*
C24	1.11154 (14)	0.3936 (4)	0.78078 (13)	0.0264 (6)
H24	1.0909	0.5311	0.7838	0.032*
C25	0.95806 (13)	0.2439 (4)	0.78283 (12)	0.0216 (6)
C26	0.95771 (14)	0.4223 (5)	0.82471 (13)	0.0264 (6)
H26	0.9832	0.5473	0.8173	0.032*
C27	0.92022 (14)	0.4189 (5)	0.87740 (14)	0.0322 (7)
H27	0.9204	0.5415	0.9057	0.039*
C28	0.88276 (14)	0.2383 (5)	0.88873 (14)	0.0355 (8)
H28	0.8567	0.2373	0.9243	0.043*
C29	0.88340 (15)	0.0586 (5)	0.84782 (15)	0.0347 (7)
H29	0.8579	−0.0663	0.8555	0.042*
C30	0.92130 (13)	0.0610 (5)	0.79549 (13)	0.0267 (6)
H30	0.9221	−0.0635	0.7681	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0258 (10)	0.0146 (10)	0.0292 (10)	−0.0005 (8)	0.0052 (8)	−0.0005 (8)
O2	0.0259 (10)	0.0235 (10)	0.0284 (10)	−0.0002 (8)	0.0102 (9)	0.0043 (8)
N1	0.0208 (12)	0.0124 (11)	0.0292 (12)	0.0016 (9)	0.0107 (10)	0.0000 (9)
N2	0.0195 (12)	0.0135 (11)	0.0270 (12)	0.0036 (9)	0.0055 (10)	−0.0002 (9)
N3	0.0281 (13)	0.0198 (12)	0.0298 (13)	0.0066 (10)	0.0081 (11)	−0.0010 (10)
C1	0.0213 (14)	0.0136 (13)	0.0226 (13)	−0.0012 (11)	0.0060 (11)	−0.0004 (10)
C2	0.0205 (14)	0.0168 (14)	0.0201 (13)	0.0014 (11)	−0.0007 (11)	−0.0001 (11)
C3	0.0241 (15)	0.0180 (14)	0.0198 (13)	0.0009 (12)	0.0045 (12)	0.0005 (11)
C4	0.0206 (14)	0.0190 (14)	0.0183 (13)	0.0000 (11)	0.0052 (11)	−0.0046 (11)
C5	0.0236 (15)	0.0216 (15)	0.0328 (16)	−0.0013 (12)	0.0088 (13)	−0.0022 (12)
C6	0.0254 (16)	0.0313 (17)	0.0346 (17)	−0.0070 (13)	0.0057 (13)	−0.0034 (13)
C7	0.0234 (16)	0.0431 (19)	0.0278 (16)	0.0010 (14)	0.0014 (13)	−0.0044 (14)
C8	0.0256 (16)	0.0341 (17)	0.0287 (15)	0.0066 (13)	−0.0006 (13)	0.0045 (13)
C9	0.0257 (15)	0.0241 (15)	0.0239 (14)	−0.0011 (12)	0.0026 (12)	0.0022 (11)
C10	0.0153 (13)	0.0207 (14)	0.0247 (14)	0.0014 (11)	0.0040 (11)	−0.0021 (11)
C11	0.0267 (15)	0.0204 (15)	0.0281 (15)	0.0003 (12)	−0.0006 (13)	0.0005 (12)
C12	0.0323 (17)	0.0249 (16)	0.0331 (16)	0.0027 (13)	−0.0041 (14)	−0.0077 (13)
C13	0.0242 (16)	0.0375 (18)	0.0254 (15)	0.0082 (13)	−0.0001 (12)	−0.0067 (13)
C14	0.0291 (16)	0.0319 (17)	0.0282 (15)	0.0054 (13)	0.0101 (13)	0.0050 (13)
C15	0.0283 (16)	0.0215 (15)	0.0292 (15)	0.0014 (12)	0.0088 (13)	0.0004 (12)
O3	0.0360 (12)	0.0214 (10)	0.0247 (10)	−0.0002 (9)	−0.0018 (9)	−0.0042 (8)
O4	0.0294 (11)	0.0136 (10)	0.0275 (10)	−0.0019 (8)	0.0035 (8)	−0.0010 (8)
N4	0.0302 (13)	0.0122 (11)	0.0214 (12)	−0.0008 (10)	−0.0024 (10)	0.0014 (9)
N5	0.0217 (12)	0.0153 (11)	0.0219 (11)	0.0006 (9)	0.0040 (10)	0.0016 (9)
N6	0.0259 (13)	0.0206 (12)	0.0254 (12)	0.0031 (10)	0.0040 (10)	0.0070 (10)
C16	0.0246 (15)	0.0122 (13)	0.0226 (13)	−0.0020 (11)	0.0017 (11)	−0.0024 (11)
C17	0.0150 (13)	0.0187 (14)	0.0208 (13)	0.0000 (11)	0.0036 (11)	−0.0008 (11)
C18	0.0194 (14)	0.0177 (14)	0.0244 (14)	−0.0005 (11)	0.0014 (12)	−0.0004 (11)
C19	0.0224 (14)	0.0196 (14)	0.0171 (13)	0.0010 (11)	0.0045 (11)	0.0010 (11)
C20	0.0256 (16)	0.0180 (15)	0.0361 (16)	−0.0013 (12)	0.0060 (13)	−0.0017 (12)
C21	0.0273 (16)	0.0201 (15)	0.0444 (18)	0.0040 (12)	0.0074 (14)	0.0044 (13)
C22	0.0234 (15)	0.0331 (17)	0.0277 (15)	0.0026 (13)	0.0009 (13)	0.0051 (12)
C23	0.0282 (16)	0.0295 (17)	0.0331 (16)	−0.0020 (13)	−0.0006 (13)	−0.0063 (13)
C24	0.0259 (16)	0.0214 (15)	0.0306 (15)	0.0015 (12)	−0.0010 (13)	−0.0049 (12)
C25	0.0196 (14)	0.0218 (14)	0.0223 (13)	0.0008 (11)	−0.0005 (11)	0.0048 (11)
C26	0.0273 (16)	0.0259 (15)	0.0259 (15)	0.0023 (13)	0.0025 (12)	0.0013 (12)
C27	0.0294 (17)	0.0413 (19)	0.0266 (15)	0.0058 (14)	0.0064 (13)	0.0005 (13)
C28	0.0249 (16)	0.055 (2)	0.0269 (16)	0.0029 (15)	0.0056 (13)	0.0110 (15)
C29	0.0253 (16)	0.0420 (19)	0.0357 (17)	−0.0092 (14)	−0.0004 (14)	0.0117 (15)
C30	0.0225 (15)	0.0284 (16)	0.0284 (15)	−0.0046 (12)	0.0001 (12)	0.0059 (12)

O1—C2	1.226 (3)	O3—C18	1.218 (3)
O2—C3	1.214 (3)	O4—C17	1.222 (3)
N1—C3	1.344 (3)	N4—C18	1.342 (3)
N1—C1	1.462 (3)	N4—C16	1.463 (3)
N1—H1	0.9100	N4—H4	0.9100
N2—C2	1.347 (3)	N5—C17	1.350 (3)
N2—N3	1.408 (3)	N5—N6	1.410 (3)
N2—C3	1.417 (3)	N5—C18	1.410 (3)
N3—H3A	0.9100	N6—H6A	0.9101
N3—H3B	0.9100	N6—H6B	0.9099
C1—C4	1.533 (4)	C16—C17	1.532 (3)
C1—C2	1.536 (3)	C16—C25	1.536 (3)
C1—C10	1.543 (3)	C16—C19	1.537 (4)
C4—C9	1.386 (4)	C19—C20	1.388 (4)
C4—C5	1.394 (4)	C19—C24	1.392 (4)
C5—C6	1.379 (4)	C20—C21	1.389 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.386 (4)	C21—C22	1.371 (4)
C6—H6C	0.9500	C21—H21	0.9500
C7—C8	1.379 (4)	C22—C23	1.385 (4)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.385 (4)	C23—C24	1.383 (4)
C8—H8	0.9500	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C10—C15	1.388 (4)	C25—C26	1.392 (4)
C10—C11	1.398 (4)	C25—C30	1.392 (4)
C11—C12	1.384 (4)	C26—C27	1.392 (4)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.379 (4)	C27—C28	1.382 (4)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.378 (4)	C28—C29	1.386 (4)
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.392 (4)	C29—C30	1.391 (4)
C14—H14	0.9500	C29—H29	0.9500
C15—H15	0.9500	C30—H30	0.9500
C3—N1—C1	113.9 (2)	C18—N4—C16	114.2 (2)
C3—N1—H1	126.1	C18—N4—H4	122.6
C1—N1—H1	119.5	C16—N4—H4	121.8
C2—N2—N3	125.8 (2)	C17—N5—N6	125.7 (2)
C2—N2—C3	112.1 (2)	C17—N5—C18	111.8 (2)
N3—N2—C3	121.4 (2)	N6—N5—C18	121.5 (2)
N2—N3—H3A	107.0	N5—N6—H6A	108.6
N2—N3—H3B	109.0	N5—N6—H6B	104.8
H3A—N3—H3B	112.1	H6A—N6—H6B	106.7
N1—C1—C4	112.5 (2)	N4—C16—C17	99.47 (19)
N1—C1—C2	99.74 (19)	N4—C16—C25	112.2 (2)
C4—C1—C2	113.6 (2)	C17—C16—C25	111.1 (2)
N1—C1—C10	111.8 (2)	N4—C16—C19	112.2 (2)
C4—C1—C10	109.8 (2)	C17—C16—C19	111.2 (2)
C2—C1—C10	109.2 (2)	C25—C16—C19	110.4 (2)
O1—C2—N2	125.9 (2)	O4—C17—N5	125.6 (2)
O1—C2—C1	126.4 (2)	O4—C17—C16	126.2 (2)
N2—C2—C1	107.7 (2)	N5—C17—C16	108.2 (2)
O2—C3—N1	128.6 (2)	O3—C18—N4	127.9 (2)
O2—C3—N2	125.4 (2)	O3—C18—N5	125.9 (2)
N1—C3—N2	105.9 (2)	N4—C18—N5	106.2 (2)
C9—C4—C5	118.6 (3)	C20—C19—C24	118.2 (2)
C9—C4—C1	120.6 (2)	C20—C19—C16	120.3 (2)
C5—C4—C1	120.7 (2)	C24—C19—C16	121.4 (2)
C6—C5—C4	120.3 (3)	C19—C20—C21	120.7 (3)
C6—C5—H5	119.8	C19—C20—H20	119.6
C4—C5—H5	119.8	C21—C20—H20	119.6
C5—C6—C7	120.8 (3)	C22—C21—C20	120.7 (3)
C5—C6—H6C	119.6	C22—C21—H21	119.6
C7—C6—H6C	119.6	C20—C21—H21	119.6
C8—C7—C6	119.1 (3)	C21—C22—C23	119.1 (3)
C8—C7—H7	120.5	C21—C22—H22	120.4
C6—C7—H7	120.5	C23—C22—H22	120.4
C7—C8—C9	120.5 (3)	C24—C23—C22	120.5 (3)
C7—C8—H8	119.8	C24—C23—H23	119.7
C9—C8—H8	119.8	C22—C23—H23	119.7
C8—C9—C4	120.7 (3)	C23—C24—C19	120.8 (3)
C8—C9—H9	119.7	C23—C24—H24	119.6
C4—C9—H9	119.7	C19—C24—H24	119.6
C15—C10—C11	118.4 (2)	C26—C25—C30	118.7 (3)
C15—C10—C1	121.9 (2)	C26—C25—C16	120.8 (2)
C11—C10—C1	119.7 (2)	C30—C25—C16	120.5 (2)
C12—C11—C10	120.4 (3)	C25—C26—C27	120.5 (3)
C12—C11—H11	119.8	C25—C26—H26	119.8
C10—C11—H11	119.8	C27—C26—H26	119.8
C13—C12—C11	120.9 (3)	C28—C27—C26	120.4 (3)
C13—C12—H12	119.5	C28—C27—H27	119.8
C11—C12—H12	119.5	C26—C27—H27	119.8
C14—C13—C12	119.0 (3)	C27—C28—C29	119.6 (3)
C14—C13—H13	120.5	C27—C28—H28	120.2
C12—C13—H13	120.5	C29—C28—H28	120.2
C13—C14—C15	120.7 (3)	C28—C29—C30	120.0 (3)
C13—C14—H14	119.6	C28—C29—H29	120.0
C15—C14—H14	119.6	C30—C29—H29	120.0
C10—C15—C14	120.5 (3)	C29—C30—C25	120.7 (3)
C10—C15—H15	119.7	C29—C30—H30	119.6
C14—C15—H15	119.7	C25—C30—H30	119.6
C3—N1—C1—C4	−128.7 (2)	C18—N4—C16—C17	3.9 (3)
C3—N1—C1—C2	−8.0 (3)	C18—N4—C16—C25	121.4 (2)
C3—N1—C1—C10	107.3 (2)	C18—N4—C16—C19	−113.7 (2)
N3—N2—C2—O1	−12.5 (4)	N6—N5—C17—O4	11.6 (4)
C3—N2—C2—O1	177.1 (2)	C18—N5—C17—O4	180.0 (2)
N3—N2—C2—C1	167.5 (2)	N6—N5—C17—C16	−168.9 (2)
C3—N2—C2—C1	−2.9 (3)	C18—N5—C17—C16	−0.5 (3)
N1—C1—C2—O1	−173.8 (2)	N4—C16—C17—O4	177.7 (3)
C4—C1—C2—O1	−53.9 (3)	C25—C16—C17—O4	59.4 (3)
C10—C1—C2—O1	68.9 (3)	C19—C16—C17—O4	−63.9 (3)
N1—C1—C2—N2	6.2 (2)	N4—C16—C17—N5	−1.9 (3)
C4—C1—C2—N2	126.1 (2)	C25—C16—C17—N5	−120.2 (2)
C10—C1—C2—N2	−111.1 (2)	C19—C16—C17—N5	116.5 (2)
C1—N1—C3—O2	−175.5 (3)	C16—N4—C18—O3	177.1 (3)
C1—N1—C3—N2	6.7 (3)	C16—N4—C18—N5	−4.4 (3)
C2—N2—C3—O2	180.0 (3)	C17—N5—C18—O3	−178.5 (3)
N3—N2—C3—O2	9.1 (4)	N6—N5—C18—O3	−9.5 (4)
C2—N2—C3—N1	−2.1 (3)	C17—N5—C18—N4	2.9 (3)
N3—N2—C3—N1	−173.0 (2)	N6—N5—C18—N4	171.9 (2)
N1—C1—C4—C9	−21.0 (3)	N4—C16—C19—C20	−25.0 (3)
C2—C1—C4—C9	−133.3 (2)	C17—C16—C19—C20	−135.4 (2)
C10—C1—C4—C9	104.2 (3)	C25—C16—C19—C20	100.9 (3)
N1—C1—C4—C5	162.1 (2)	N4—C16—C19—C24	158.5 (2)
C2—C1—C4—C5	49.7 (3)	C17—C16—C19—C24	48.1 (3)
C10—C1—C4—C5	−72.8 (3)	C25—C16—C19—C24	−75.6 (3)
C9—C4—C5—C6	0.4 (4)	C24—C19—C20—C21	−0.1 (4)
C1—C4—C5—C6	177.5 (2)	C16—C19—C20—C21	−176.8 (2)
C4—C5—C6—C7	−0.4 (4)	C19—C20—C21—C22	−0.1 (4)
C5—C6—C7—C8	−0.3 (4)	C20—C21—C22—C23	0.0 (4)
C6—C7—C8—C9	1.0 (4)	C21—C22—C23—C24	0.3 (4)
C7—C8—C9—C4	−1.0 (4)	C22—C23—C24—C19	−0.5 (4)
C5—C4—C9—C8	0.3 (4)	C20—C19—C24—C23	0.4 (4)
C1—C4—C9—C8	−176.8 (2)	C16—C19—C24—C23	177.0 (2)
N1—C1—C10—C15	−153.5 (2)	N4—C16—C25—C26	−160.2 (2)
C4—C1—C10—C15	80.9 (3)	C17—C16—C25—C26	−49.8 (3)
C2—C1—C10—C15	−44.2 (3)	C19—C16—C25—C26	73.9 (3)
N1—C1—C10—C11	28.9 (3)	N4—C16—C25—C30	21.3 (3)
C4—C1—C10—C11	−96.7 (3)	C17—C16—C25—C30	131.6 (3)
C2—C1—C10—C11	138.3 (2)	C19—C16—C25—C30	−104.6 (3)
C15—C10—C11—C12	0.9 (4)	C30—C25—C26—C27	−1.2 (4)
C1—C10—C11—C12	178.6 (2)	C16—C25—C26—C27	−179.8 (2)
C10—C11—C12—C13	0.4 (4)	C25—C26—C27—C28	−0.1 (4)
C11—C12—C13—C14	−1.0 (4)	C26—C27—C28—C29	0.9 (4)
C12—C13—C14—C15	0.2 (4)	C27—C28—C29—C30	−0.4 (4)
C11—C10—C15—C14	−1.6 (4)	C28—C29—C30—C25	−1.0 (4)
C1—C10—C15—C14	−179.3 (2)	C26—C25—C30—C29	1.8 (4)
C13—C14—C15—C10	1.1 (4)	C16—C25—C30—C29	−179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.91	1.92	2.828 (3)	177
N3—H3A···O3	0.91	2.11	2.957 (3)	154
N4—H4···O4ii	0.91	1.91	2.820 (3)	176
N6—H6A···O3i	0.91	2.58	3.320 (3)	139
N6—H6B···O2iii	0.91	2.46	3.070 (3)	124
N6—H6B···N3iii	0.91	2.52	3.363 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.91	1.92	2.828 (3)	177
N3—H3A⋯O3	0.91	2.11	2.957 (3)	154
N4—H4⋯O4ii	0.91	1.91	2.820 (3)	176
N6—H6A⋯O3i	0.91	2.58	3.320 (3)	139
N6—H6B⋯O2iii	0.91	2.46	3.070 (3)	124
N6—H6B⋯N3iii	0.91	2.52	3.363 (3)	154

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