1-[4-(Diamino-methyl-eneamino-sulfon-yl)phenyl-iminiometh-yl]-2-naphtholate N,N-dimethyl-formamide disolvate.

The asymmetric unit the title compound, C(18)H(16)N(4)O(3)S·2C(3)H(7)NO, contains a mol-ecule in a zwitterionic form with a deprotonated hydroxyl group and an iminium group, and two dimethyl-formamide solvent mol-ecules. The dihedral angles of the guanidine group and the naphthyl ring system with respect to the central benzene ring are 76.04 (7) and 3.45 (9)°, respectively. The conformation of the mol-ecule may be influenced, in part, by two intra-molecular hydrogen bonds, while in the crystal structure, inter-molecular hydrogen bonds form one-dimensional chains along [010].

Related literature

For related literature, see: Arestrup (1999 ▶); Bergant et al. (1993 ▶); Boghaei et al. (2000 ▶); Esposito et al. (2000 ▶); Ganolkar (1985 ▶); Hao & Shen (2000 ▶); Jain & Chaturvedi (1977 ▶); Jeewoth et al. (2000 ▶); Johnson et al. (1982 ▶); Kwiatkowski et al. (2003 ▶); Lal (1979 ▶); Maki & Hashimato (1952 ▶); Papie et al. (1994 ▶); Raman et al. (2003 ▶); Srinivasan et al. (1986 ▶); Wu & Lu (2003 ▶); Tantaru et al. (2002 ▶).

Experimental

Crystal data

C18H16N4O3S·2C3H7NO

M = 514.60

Monoclinic,

a = 8.5910 (11) Å

b = 9.9101 (12) Å

c = 15.1762 (19) Å

β = 106.327 (1)°

V = 1240.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 100 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.775, T max = 0.965

13950 measured reflections

5450 independent reflections

5190 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.08

5450 reflections

329 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983), 2555 Friedel pairs

Flack parameter: −0.03 (6)

Data collection: APEX2 (Bruker, 2006 ▶); 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: KENX (Sakai, 2004 ▶); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001 ▶), KENX and ORTEPII (Johnson, 1976 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018710/lh2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018710/lh2634Isup2.hkl

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

C18H16N4O3S·2C3H7NO	F000 = 544
Mr = 514.60	Dx = 1.378 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7706 reflections
a = 8.5910 (11) Å	θ = 2.5–28.3º
b = 9.9101 (12) Å	µ = 0.18 mm−1
c = 15.1762 (19) Å	T = 100 (2) K
β = 106.327 (1)º	Cube, yellow
V = 1240.0 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 2

Bruker SMART APEX CCD-detector diffractometer	5450 independent reflections
Radiation source: sealed tube	5190 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 100(2) K	θmax = 27.1º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.775, Tmax = 0.965	k = −12→12
13950 measured reflections	l = −19→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.3529P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.47 e Å−3
5450 reflections	Δρmin = −0.22 e Å−3
329 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 2555 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (6)
Secondary atom site location: difference Fourier map

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)5.2137 (0.0068) x - 0.3949 (0.0103) y + 8.9719 (0.0123) z = 4.0913 (0.0088)* -0.0014 (0.0004) N1 * -0.0016 (0.0005) N2 * -0.0016 (0.0005) N3 * 0.0047 (0.0014) C1Rms deviation of fitted atoms = 0.0027- 6.1727 (0.0045) x + 6.3206 (0.0058) y + 7.1057 (0.0101) z = 8.7939 (0.0072)Angle to previous plane (with approximate e.s.d.) = 76.04 (0.07)* 0.0058 (0.0013) C2 * 0.0060 (0.0013) C3 * -0.0134 (0.0013) C4 * 0.0091 (0.0013) C5 * 0.0025 (0.0013) C6 * -0.0100 (0.0013) C7 0.0707 (0.0027) N4 0.1033 (0.0034) C8Rms deviation of fitted atoms = 0.0085- 6.1442 (0.0026) x + 6.5659 (0.0029) y + 6.2926 (0.0042) z = 8.2691 (0.0057)Angle to previous plane (with approximate e.s.d.) = 3.45 (0.09)* 0.0103 (0.0013) N4 * -0.0338 (0.0015) C8 * -0.0052 (0.0016) C9 * 0.0523 (0.0016) C10 * 0.0115 (0.0016) C11 * -0.0294 (0.0016) C12 * -0.0226 (0.0017) C13 * -0.0027 (0.0016) C14 * 0.0199 (0.0017) C15 * 0.0248 (0.0017) C16 * -0.0069 (0.0018) C17 * -0.0184 (0.0017) C18Rms deviation of fitted atoms = 0.0240- 6.1272 (0.0029) x + 6.5698 (0.0029) y + 6.3590 (0.0070) z = 8.3630 (0.0094)Angle to previous plane (with approximate e.s.d.) = 0.32 (0.06)* -0.0161 (0.0015) C9 * 0.0447 (0.0015) C10 * 0.0118 (0.0016) C11 * -0.0248 (0.0016) C12 * -0.0211 (0.0017) C13 * 0.0034 (0.0016) C14 * 0.0230 (0.0017) C15 * 0.0202 (0.0017) C16 * -0.0161 (0.0016) C17 * -0.0248 (0.0016) C18 - 0.0128 (0.0027) N4 - 0.0526 (0.0025) C8 0.1229 (0.0022) O3Rms deviation of fitted atoms = 0.0230

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
S1	−0.11893 (5)	0.64754 (4)	0.56177 (3)	0.01452 (10)
O1	−0.24764 (16)	0.55840 (14)	0.56814 (9)	0.0193 (3)
O2	−0.16593 (16)	0.78608 (13)	0.53549 (9)	0.0194 (3)
O3	0.57291 (18)	0.81413 (15)	1.04536 (10)	0.0256 (3)
O4	−0.0111 (3)	0.32634 (18)	0.94460 (18)	0.0650 (7)
O5	0.72580 (19)	0.28022 (15)	0.68340 (11)	0.0285 (3)
N1	0.1366 (2)	0.56994 (16)	0.40154 (11)	0.0206 (3)
N2	0.0756 (2)	0.77841 (17)	0.44614 (12)	0.0218 (4)
N3	−0.02653 (19)	0.57624 (15)	0.49661 (10)	0.0165 (3)
N4	0.3407 (2)	0.68157 (15)	0.93727 (11)	0.0182 (3)
N5	0.0840 (2)	0.11583 (17)	0.93544 (12)	0.0260 (4)
N6	0.5259 (2)	0.43169 (17)	0.68153 (12)	0.0219 (4)
C1	0.0599 (2)	0.6446 (2)	0.45009 (11)	0.0163 (3)
C2	0.0195 (2)	0.6549 (2)	0.67283 (11)	0.0152 (3)
C3	0.1424 (2)	0.75172 (18)	0.69345 (13)	0.0186 (4)
C4	0.2502 (2)	0.75575 (19)	0.78083 (13)	0.0190 (4)
C5	0.2327 (2)	0.66596 (18)	0.84865 (12)	0.0169 (4)
C6	0.1098 (2)	0.56887 (18)	0.82732 (13)	0.0183 (4)
C7	0.0047 (2)	0.56322 (19)	0.73931 (12)	0.0180 (4)
C8	0.3396 (2)	0.60541 (19)	1.00860 (13)	0.0184 (4)
C9	0.4473 (2)	0.62620 (18)	1.09660 (13)	0.0176 (4)
C10	0.5652 (2)	0.73244 (19)	1.11006 (13)	0.0197 (4)
C11	0.6790 (2)	0.74704 (19)	1.19945 (14)	0.0222 (4)
C12	0.6721 (2)	0.6666 (2)	1.27010 (13)	0.0224 (4)
C13	0.5510 (2)	0.56323 (19)	1.26085 (13)	0.0191 (4)
C14	0.5425 (2)	0.4853 (2)	1.33700 (13)	0.0223 (4)
C15	0.4250 (3)	0.3869 (2)	1.32851 (15)	0.0248 (4)
C16	0.3137 (2)	0.3655 (2)	1.24287 (15)	0.0236 (4)
C17	0.3208 (2)	0.4402 (2)	1.16690 (13)	0.0221 (4)
C18	0.4381 (2)	0.54178 (19)	1.17358 (13)	0.0179 (4)
C19	−0.0038 (3)	0.2224 (2)	0.90039 (19)	0.0373 (6)
C20	0.1016 (3)	0.0011 (2)	0.87992 (17)	0.0332 (5)
C21	0.1793 (4)	0.1120 (3)	1.03111 (17)	0.0470 (7)
C22	0.5933 (3)	0.3374 (2)	0.64427 (16)	0.0282 (5)
C23	0.5988 (3)	0.4800 (2)	0.77380 (15)	0.0324 (5)
C24	0.3774 (3)	0.4992 (3)	0.62885 (18)	0.0399 (6)
H1A	0.1939	0.6095	0.3691	0.025*
H1B	0.1297	0.4814	0.4021	0.025*
H2A	0.1342	0.8135	0.4128	0.026*
H2B	0.0274	0.8314	0.4769	0.026*
H4A	0.4136	0.7462	0.9456	0.022*
H3	0.1522	0.8145	0.6480	0.022*
H4	0.3362	0.8196	0.7946	0.023*
H6	0.0983	0.5070	0.8729	0.022*
H7	−0.0777	0.4963	0.7244	0.022*
H8	0.2632	0.5339	1.0002	0.022*
H11	0.7606	0.8145	1.2090	0.027*
H12	0.7499	0.6787	1.3280	0.027*
H14	0.6186	0.5005	1.3950	0.027*
H15	0.4201	0.3347	1.3802	0.030*
H16	0.2318	0.2988	1.2366	0.028*
H17	0.2449	0.4224	1.1091	0.026*
H19	−0.0651	0.2194	0.8377	0.045*
H20A	0.0285	0.0114	0.8178	0.050*
H20B	0.0744	−0.0819	0.9075	0.050*
H20C	0.2139	−0.0040	0.8768	0.050*
H21A	0.1438	0.1844	1.0649	0.071*
H21B	0.2943	0.1243	1.0351	0.071*
H21C	0.1642	0.0246	1.0578	0.071*
H22	0.5385	0.3102	0.5834	0.034*
H23A	0.6502	0.5676	0.7713	0.049*
H23B	0.6807	0.4153	0.8069	0.049*
H23C	0.5148	0.4898	0.8057	0.049*
H24A	0.3318	0.4510	0.5710	0.060*
H24B	0.4024	0.5923	0.6158	0.060*
H24C	0.2983	0.4996	0.6645	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0178 (2)	0.01154 (19)	0.01503 (19)	0.00018 (18)	0.00590 (15)	0.00046 (17)
O1	0.0198 (7)	0.0192 (6)	0.0197 (6)	−0.0020 (5)	0.0066 (5)	0.0012 (5)
O2	0.0234 (7)	0.0159 (6)	0.0193 (6)	0.0038 (5)	0.0067 (6)	0.0021 (5)
O3	0.0315 (8)	0.0220 (7)	0.0236 (7)	−0.0062 (6)	0.0079 (6)	0.0012 (6)
O4	0.1020 (18)	0.0211 (9)	0.1044 (19)	0.0118 (10)	0.0820 (16)	0.0082 (10)
O5	0.0310 (8)	0.0228 (7)	0.0381 (9)	0.0026 (6)	0.0202 (7)	0.0000 (7)
N1	0.0297 (9)	0.0127 (7)	0.0241 (8)	0.0003 (7)	0.0154 (7)	0.0010 (6)
N2	0.0305 (9)	0.0127 (8)	0.0286 (9)	−0.0008 (7)	0.0189 (8)	0.0002 (7)
N3	0.0235 (8)	0.0120 (7)	0.0153 (7)	0.0010 (6)	0.0076 (6)	−0.0007 (6)
N4	0.0199 (8)	0.0150 (8)	0.0192 (8)	−0.0021 (6)	0.0045 (6)	−0.0006 (6)
N5	0.0352 (10)	0.0159 (9)	0.0279 (9)	−0.0014 (7)	0.0104 (8)	−0.0012 (6)
N6	0.0219 (8)	0.0188 (8)	0.0255 (9)	−0.0017 (7)	0.0076 (7)	−0.0011 (7)
C1	0.0196 (8)	0.0152 (8)	0.0130 (7)	0.0028 (8)	0.0030 (6)	0.0020 (8)
C2	0.0180 (8)	0.0146 (8)	0.0130 (7)	0.0022 (8)	0.0044 (6)	−0.0016 (8)
C3	0.0251 (10)	0.0147 (9)	0.0177 (9)	−0.0017 (7)	0.0087 (8)	0.0008 (7)
C4	0.0226 (10)	0.0135 (9)	0.0227 (10)	−0.0046 (7)	0.0095 (8)	−0.0034 (7)
C5	0.0209 (8)	0.0140 (9)	0.0170 (8)	0.0020 (7)	0.0071 (7)	−0.0019 (7)
C6	0.0240 (10)	0.0139 (9)	0.0180 (9)	−0.0004 (7)	0.0077 (7)	0.0025 (7)
C7	0.0194 (9)	0.0153 (8)	0.0206 (9)	−0.0014 (7)	0.0078 (7)	0.0003 (7)
C8	0.0191 (9)	0.0155 (8)	0.0211 (9)	0.0001 (7)	0.0064 (7)	−0.0013 (7)
C9	0.0195 (9)	0.0153 (9)	0.0187 (8)	0.0025 (7)	0.0063 (7)	−0.0008 (7)
C10	0.0230 (10)	0.0161 (9)	0.0212 (9)	0.0008 (7)	0.0083 (8)	−0.0031 (7)
C11	0.0202 (10)	0.0189 (10)	0.0270 (10)	−0.0025 (8)	0.0060 (8)	−0.0069 (8)
C12	0.0206 (9)	0.0251 (10)	0.0193 (9)	0.0025 (8)	0.0022 (7)	−0.0069 (8)
C13	0.0210 (9)	0.0173 (9)	0.0197 (9)	0.0060 (7)	0.0070 (7)	−0.0035 (8)
C14	0.0258 (10)	0.0237 (10)	0.0166 (9)	0.0067 (8)	0.0046 (8)	−0.0033 (8)
C15	0.0316 (12)	0.0230 (10)	0.0224 (10)	0.0065 (8)	0.0119 (9)	0.0048 (8)
C16	0.0238 (10)	0.0198 (9)	0.0292 (11)	−0.0006 (8)	0.0105 (9)	0.0015 (8)
C17	0.0228 (10)	0.0209 (10)	0.0206 (9)	−0.0007 (8)	0.0032 (8)	0.0002 (8)
C18	0.0193 (9)	0.0163 (9)	0.0190 (9)	0.0046 (7)	0.0067 (7)	−0.0014 (7)
C19	0.0469 (15)	0.0264 (11)	0.0488 (15)	0.0044 (11)	0.0305 (13)	0.0093 (11)
C20	0.0371 (12)	0.0213 (11)	0.0470 (14)	−0.0036 (9)	0.0210 (11)	−0.0056 (10)
C21	0.0679 (19)	0.0395 (15)	0.0297 (12)	−0.0226 (13)	0.0070 (12)	0.0037 (10)
C22	0.0337 (12)	0.0260 (11)	0.0275 (11)	−0.0041 (9)	0.0127 (9)	0.0000 (9)
C23	0.0342 (12)	0.0307 (12)	0.0328 (12)	−0.0030 (10)	0.0105 (10)	−0.0056 (10)
C24	0.0348 (13)	0.0313 (13)	0.0472 (15)	0.0062 (10)	0.0011 (11)	−0.0024 (11)

S1—O1	1.4397 (14)	N6—C22	1.308 (3)
S1—O2	1.4549 (14)	N6—C23	1.445 (3)
S1—N3	1.5963 (16)	N6—C24	1.464 (3)
S1—C2	1.7702 (17)	N1—H1A	0.8800
O3—C10	1.289 (2)	N1—H1B	0.8800
O4—C19	1.240 (3)	N2—H2A	0.8800
O5—C22	1.261 (3)	N2—H2B	0.8800
N1—C1	1.341 (2)	N4—H4A	0.8800
N2—C1	1.336 (2)	C3—H3	0.9500
N3—C1	1.343 (2)	C4—H4	0.9500
N4—C8	1.322 (2)	C6—H6	0.9500
N4—C5	1.411 (2)	C7—H7	0.9500
C2—C7	1.389 (3)	C8—H8	0.9500
C2—C3	1.396 (3)	C11—H11	0.9500
C3—C4	1.388 (3)	C12—H12	0.9500
C4—C5	1.400 (3)	C14—H14	0.9500
C5—C6	1.398 (3)	C15—H15	0.9500
C6—C7	1.387 (3)	C16—H16	0.9500
C8—C9	1.410 (3)	C17—H17	0.9500
C9—C10	1.435 (3)	C19—H19	0.9500
C9—C18	1.457 (3)	C20—H20A	0.9800
C10—C11	1.439 (3)	C20—H20B	0.9800
C11—C12	1.351 (3)	C20—H20C	0.9800
C12—C13	1.438 (3)	C21—H21A	0.9800
C13—C14	1.409 (3)	C21—H21B	0.9800
C13—C18	1.421 (3)	C21—H21C	0.9800
C14—C15	1.383 (3)	C22—H22	0.9500
C15—C16	1.396 (3)	C23—H23A	0.9800
C16—C17	1.385 (3)	C23—H23B	0.9800
C17—C18	1.408 (3)	C23—H23C	0.9800
N5—C19	1.320 (3)	C24—H24A	0.9800
N5—C20	1.448 (3)	C24—H24B	0.9800
N5—C21	1.453 (3)	C24—H24C	0.9800
O1—S1—O2	115.99 (8)	C12—C11—H11	119.4
O1—S1—N3	107.16 (8)	C10—C11—H11	119.4
O2—S1—N3	113.33 (8)	C11—C12—C13	122.34 (18)
O1—S1—C2	106.52 (8)	C11—C12—H12	118.8
O2—S1—C2	106.42 (9)	C13—C12—H12	118.8
N3—S1—C2	106.86 (8)	C14—C13—C18	120.20 (18)
C1—N1—H1A	120.0	C14—C13—C12	120.89 (18)
C1—N1—H1B	120.0	C18—C13—C12	118.90 (17)
H1A—N1—H1B	120.0	C15—C14—C13	120.99 (19)
C1—N2—H2A	120.0	C15—C14—H14	119.5
C1—N2—H2B	120.0	C13—C14—H14	119.5
H2A—N2—H2B	120.0	C14—C15—C16	119.00 (19)
C1—N3—S1	123.17 (13)	C14—C15—H15	120.5
C8—N4—C5	124.29 (16)	C16—C15—H15	120.5
C8—N4—H4A	117.9	C17—C16—C15	120.97 (19)
C5—N4—H4A	117.9	C17—C16—H16	119.5
C19—N5—C20	122.4 (2)	C15—C16—H16	119.5
C19—N5—C21	121.4 (2)	C16—C17—C18	121.32 (18)
C20—N5—C21	116.0 (2)	C16—C17—H17	119.3
C22—N6—C23	122.12 (19)	C18—C17—H17	119.3
C22—N6—C24	120.95 (19)	C17—C18—C13	117.50 (17)
C23—N6—C24	116.83 (19)	C17—C18—C9	123.51 (17)
N2—C1—N1	116.84 (17)	C13—C18—C9	118.98 (17)
N2—C1—N3	127.02 (17)	O4—C19—N5	123.8 (3)
N1—C1—N3	116.14 (17)	O4—C19—H19	118.1
C7—C2—C3	120.29 (16)	N5—C19—H19	118.1
C7—C2—S1	119.38 (14)	N5—C20—H20A	109.5
C3—C2—S1	120.34 (14)	N5—C20—H20B	109.5
C4—C3—C2	119.58 (17)	H20A—C20—H20B	109.5
C4—C3—H3	120.2	N5—C20—H20C	109.5
C2—C3—H3	120.2	H20A—C20—H20C	109.5
C3—C4—C5	120.20 (17)	H20B—C20—H20C	109.5
C3—C4—H4	119.9	N5—C21—H21A	109.5
C5—C4—H4	119.9	N5—C21—H21B	109.5
C6—C5—C4	119.83 (17)	H21A—C21—H21B	109.5
C6—C5—N4	123.21 (16)	N5—C21—H21C	109.5
C4—C5—N4	116.94 (17)	H21A—C21—H21C	109.5
C7—C6—C5	119.71 (16)	H21B—C21—H21C	109.5
C7—C6—H6	120.1	O5—C22—N6	124.6 (2)
C5—C6—H6	120.1	O5—C22—H22	117.7
C6—C7—C2	120.35 (17)	N6—C22—H22	117.7
C6—C7—H7	119.8	N6—C23—H23A	109.5
C2—C7—H7	119.8	N6—C23—H23B	109.5
N4—C8—C9	122.57 (17)	H23A—C23—H23B	109.5
N4—C8—H8	118.7	N6—C23—H23C	109.5
C9—C8—H8	118.7	H23A—C23—H23C	109.5
C8—C9—C10	119.41 (17)	H23B—C23—H23C	109.5
C8—C9—C18	120.43 (17)	N6—C24—H24A	109.5
C10—C9—C18	120.16 (17)	N6—C24—H24B	109.5
O3—C10—C9	122.53 (18)	H24A—C24—H24B	109.5
O3—C10—C11	119.23 (18)	N6—C24—H24C	109.5
C9—C10—C11	118.24 (17)	H24A—C24—H24C	109.5
C12—C11—C10	121.26 (18)	H24B—C24—H24C	109.5
O1—S1—N3—C1	156.25 (14)	C18—C9—C10—O3	−176.40 (17)
O2—S1—N3—C1	27.00 (17)	C8—C9—C10—C11	−176.88 (17)
C2—S1—N3—C1	−89.89 (16)	C18—C9—C10—C11	3.8 (3)
S1—N3—C1—N2	−3.9 (3)	O3—C10—C11—C12	177.77 (18)
S1—N3—C1—N1	177.04 (13)	C9—C10—C11—C12	−2.4 (3)
O1—S1—C2—C7	11.77 (17)	C10—C11—C12—C13	−0.6 (3)
O2—S1—C2—C7	136.09 (15)	C11—C12—C13—C14	−176.99 (18)
N3—S1—C2—C7	−102.53 (15)	C11—C12—C13—C18	2.2 (3)
O1—S1—C2—C3	−168.26 (14)	C18—C13—C14—C15	0.1 (3)
O2—S1—C2—C3	−43.94 (16)	C12—C13—C14—C15	179.23 (18)
N3—S1—C2—C3	77.44 (16)	C13—C14—C15—C16	−0.1 (3)
C7—C2—C3—C4	0.2 (3)	C14—C15—C16—C17	0.7 (3)
S1—C2—C3—C4	−179.79 (14)	C15—C16—C17—C18	−1.3 (3)
C2—C3—C4—C5	−2.0 (3)	C16—C17—C18—C13	1.2 (3)
C3—C4—C5—C6	2.3 (3)	C16—C17—C18—C9	−177.82 (18)
C3—C4—C5—N4	−176.20 (17)	C14—C13—C18—C17	−0.6 (3)
C8—N4—C5—C6	1.3 (3)	C12—C13—C18—C17	−179.77 (17)
C8—N4—C5—C4	179.76 (18)	C14—C13—C18—C9	178.46 (17)
C4—C5—C6—C7	−0.8 (3)	C12—C13—C18—C9	−0.7 (3)
N4—C5—C6—C7	177.63 (17)	C8—C9—C18—C17	−2.6 (3)
C5—C6—C7—C2	−1.0 (3)	C10—C9—C18—C17	176.74 (17)
C3—C2—C7—C6	1.4 (3)	C8—C9—C18—C13	178.44 (16)
S1—C2—C7—C6	−178.68 (14)	C10—C9—C18—C13	−2.3 (3)
C5—N4—C8—C9	−178.53 (17)	C20—N5—C19—O4	−174.2 (2)
N4—C8—C9—C10	−1.0 (3)	C21—N5—C19—O4	0.8 (4)
N4—C8—C9—C18	178.27 (17)	C23—N6—C22—O5	−0.3 (3)
C8—C9—C10—O3	2.9 (3)	C24—N6—C22—O5	175.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.88	2.14	2.781 (2)	129
N4—H4A···O3	0.88	1.86	2.560 (2)	135
N1—H1B···O2i	0.88	2.14	2.959 (2)	155
N1—H1A···O5ii	0.88	2.07	2.874 (2)	152
N2—H2A···O5ii	0.88	2.16	2.943 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.88	2.14	2.781 (2)	129
N4—H4A⋯O3	0.88	1.86	2.560 (2)	135
N1—H1B⋯O2i	0.88	2.14	2.959 (2)	155
N1—H1A⋯O5ii	0.88	2.07	2.874 (2)	152
N2—H2A⋯O5ii	0.88	2.16	2.943 (2)	148

Symmetry codes: (i) ; (ii) .