4,4′-Methyl­enedianilinium 2,2′-dithio­dibenzoate

In the title mol­ecular salt, C₁₃H₁₆N₂²⁺·C₁₄H₈O₄S₂²⁻, the component species are linked into an infinite three-dimensional framework by N—H...O hydrogen bonds. The dihedral angles between the aromatic rings in the cation and the anion are 72.8 (3) and 79.5 (3)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.086
• wR factor = 0.174
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of .     257.00 A   3 

Author Response: Voids are apparently empty

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               5162
           Count of symmetry unique reflns         2896
           Completeness (_total/calc)            178.25%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2266
           Fraction of Friedel pairs measured     0.782
           Are heavy atom types Z>Si present        yes

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Crystallization for salt-like molecular crystals through hydrogen bonding interaction is a powerful tool for designing absolute asymmetric syntheses and new functional solid materials (Tan et al., 2006). Herein we report a molecular salt containing 4,4'-methylene bis(benzenammonium) (C₁₃H₁₆N₂²⁺) dications and 2,2'-dithiobis(benzoate) (C₁₄H₈O₄S₂^2-) dianions, (I). The asymmetric unit of (I) contains one dication and one dianion (Fig. 1). The dihedral angles between the aromatic rings of the dication and the dianion are 72.8 (3)° and 79.5 (3)°, respectively. The C2—S1—S2—C9 torsion angle is -86.2 (2)°.

The six hydrogen atoms bound to the two N atoms act as hydrogen bonds donors and interact with carboxylate O atoms as acceptors (Table 1). These components ions are finally organized into an infinite three-dimensional framework (Fig. 2). Large voids propagating in [001] are apparent in the structure, but the final difference map yielded no features that could be modelled as atoms occupying these spaces.

Related literature

For related literature, see: Tan et al. (2006).

S2. Experimental

A 5-ml ethanol solution of 4,4'-methylene bis(benzenamine) (0.25 mmol, 0.050 g) was added to an aqueous solution (25 ml) of 2,2'-dithiobis(benzoic acid) (0.25 mmol, 0.075 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was kept at room temperature. After a week, pink rods of (I) were obtained.

S3. Refinement

All the H atoms were placed in calculated positions with C—H = 0.93 Å and N—H = 0.89 Å, respectively, and were refined as riding with U_iso(H) = 1.2U_eq(C) or U_iso = 1.5U_eq(N).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure unit of (I). Displacement ellipsoids for the non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The infinite three-dimensional framework in (I) viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

4,4'-Methylenedianilinium 2,2'-dithiodibenzoate

Crystal data

C13H16N2^2+·C14H8O4S2^2^−	Dx = 1.268 Mg m^−3
Mr = 504.62	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 5675 reflections
Hall symbol: P -4 2n	θ = 2.1–28.2°
a = 24.4620 (15) Å	µ = 0.24 mm^−1
c = 8.8325 (10) Å	T = 292 K
V = 5285.3 (8) Å^3	Bar, pink
Z = 8	0.40 × 0.11 × 0.09 mm
F(000) = 2112

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5162 independent reflections
Radiation source: fine-focus sealed tube	4092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −30→30
Tmin = 0.912, Tmax = 0.979	k = −30→13
28154 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.086	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0782P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max < 0.001
5162 reflections	Δρmax = 0.43 e Å^−3
316 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2266 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (14)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.33512 (16)	0.73080 (15)	0.4507 (5)	0.0451 (10)
H1A	0.3521	0.7343	0.5393	0.054*
H1B	0.3066	0.7085	0.4612	0.054*
H1C	0.3236	0.7635	0.4197	0.054*
N2	0.70205 (14)	0.71797 (14)	0.0445 (4)	0.0363 (9)
H2A	0.7105	0.7347	−0.0418	0.044*
H2B	0.7251	0.6904	0.0599	0.044*
H2C	0.7046	0.7416	0.1208	0.044*
C15	0.3726 (2)	0.7084 (2)	0.3410 (6)	0.0444 (13)
C16	0.3866 (3)	0.6543 (2)	0.3499 (9)	0.076 (2)
H16	0.3717	0.6324	0.4254	0.091*
C17	0.4225 (3)	0.6324 (3)	0.2484 (9)	0.082 (2)
H17	0.4328	0.5960	0.2584	0.098*
C18	0.4438 (2)	0.6627 (3)	0.1324 (8)	0.0619 (16)
C19	0.4293 (3)	0.7165 (3)	0.1219 (8)	0.0711 (18)
H19	0.4438	0.7382	0.0454	0.085*
C20	0.3925 (2)	0.7388 (3)	0.2270 (7)	0.0635 (16)
H20	0.3818	0.7751	0.2175	0.076*
C21	0.64643 (17)	0.69709 (18)	0.0351 (5)	0.0327 (10)
C22	0.6135 (2)	0.7135 (3)	−0.0764 (7)	0.0618 (16)
H22	0.6263	0.7372	−0.1507	0.074*
C23	0.5596 (3)	0.6947 (3)	−0.0802 (7)	0.079 (2)
H23	0.5365	0.7069	−0.1566	0.095*
C24	0.5400 (2)	0.6590 (3)	0.0250 (7)	0.0577 (15)
C25	0.5752 (2)	0.6430 (2)	0.1395 (8)	0.0605 (16)
H25	0.5631	0.6191	0.2140	0.073*
C26	0.6282 (2)	0.6623 (2)	0.1440 (6)	0.0518 (14)
H26	0.6515	0.6514	0.2215	0.062*
C27	0.4827 (2)	0.6370 (3)	0.0164 (8)	0.077 (2)
H27A	0.4837	0.5978	0.0322	0.092*
H27B	0.4684	0.6436	−0.0845	0.092*
S1	0.47191 (5)	0.76473 (6)	0.60874 (17)	0.0493 (4)
S2	0.55352 (5)	0.76056 (6)	0.55829 (16)	0.0490 (4)
O1	0.33785 (14)	0.80258 (17)	0.9168 (5)	0.0677 (11)
O2	0.37348 (15)	0.75345 (17)	0.7332 (5)	0.0619 (10)
O3	0.65762 (13)	0.74742 (15)	0.5071 (4)	0.0495 (9)
O4	0.70770 (12)	0.77377 (13)	0.3123 (4)	0.0449 (8)
C1	0.41755 (18)	0.8370 (2)	0.7978 (5)	0.0385 (11)
C2	0.46407 (18)	0.82736 (19)	0.7109 (6)	0.0382 (11)
C3	0.5034 (2)	0.8683 (2)	0.7033 (6)	0.0518 (14)
H3	0.5348	0.8626	0.6457	0.062*
C4	0.4972 (2)	0.9165 (2)	0.7778 (7)	0.0616 (16)
H4	0.5240	0.9433	0.7701	0.074*
C5	0.4508 (2)	0.9257 (2)	0.8661 (8)	0.0657 (17)
H5	0.4463	0.9586	0.9171	0.079*
C6	0.4125 (2)	0.8862 (2)	0.8766 (7)	0.0532 (14)
H6	0.3821	0.8919	0.9377	0.064*
C7	0.37240 (19)	0.7948 (2)	0.8169 (7)	0.0475 (13)
C8	0.61475 (19)	0.80094 (18)	0.3180 (5)	0.0357 (11)
C9	0.56232 (18)	0.79766 (19)	0.3847 (6)	0.0393 (11)
C10	0.5198 (2)	0.8239 (2)	0.3138 (7)	0.0587 (16)
H10	0.4852	0.8225	0.3569	0.070*
C11	0.5272 (2)	0.8521 (2)	0.1804 (7)	0.0628 (17)
H11	0.4974	0.8684	0.1333	0.075*
C12	0.5776 (2)	0.8564 (2)	0.1169 (7)	0.0558 (15)
H12	0.5826	0.8760	0.0279	0.067*
C13	0.6213 (2)	0.8311 (2)	0.1867 (6)	0.0442 (13)
H13	0.6560	0.8344	0.1444	0.053*
C14	0.66339 (18)	0.77186 (17)	0.3853 (5)	0.0327 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.046 (2)	0.036 (2)	0.054 (3)	−0.0068 (18)	0.002 (2)	0.008 (2)
N2	0.040 (2)	0.034 (2)	0.035 (2)	0.0021 (17)	0.0033 (18)	−0.0010 (17)
C15	0.039 (3)	0.046 (3)	0.049 (3)	−0.008 (2)	−0.002 (2)	−0.004 (3)
C16	0.080 (4)	0.050 (4)	0.098 (5)	0.005 (3)	0.029 (4)	0.018 (4)
C17	0.082 (5)	0.053 (4)	0.110 (6)	0.012 (4)	0.029 (5)	−0.003 (4)
C18	0.035 (3)	0.078 (4)	0.073 (4)	−0.014 (3)	0.002 (3)	−0.027 (4)
C19	0.069 (4)	0.088 (5)	0.056 (4)	−0.013 (3)	0.018 (3)	0.008 (4)
C20	0.065 (4)	0.064 (4)	0.062 (4)	−0.002 (3)	0.005 (3)	0.013 (3)
C21	0.028 (2)	0.035 (2)	0.035 (3)	0.005 (2)	0.004 (2)	−0.008 (2)
C22	0.047 (3)	0.091 (4)	0.047 (3)	−0.011 (3)	−0.005 (3)	0.021 (3)
C23	0.055 (4)	0.133 (6)	0.050 (4)	−0.006 (4)	−0.015 (3)	0.016 (4)
C24	0.048 (3)	0.077 (4)	0.048 (3)	−0.004 (3)	0.014 (3)	−0.027 (3)
C25	0.048 (3)	0.068 (4)	0.066 (4)	−0.015 (3)	0.012 (3)	0.005 (3)
C26	0.044 (3)	0.062 (3)	0.049 (3)	−0.001 (3)	−0.007 (3)	0.009 (3)
C27	0.040 (3)	0.107 (5)	0.083 (5)	−0.016 (3)	0.006 (3)	−0.040 (4)
S1	0.0340 (6)	0.0482 (8)	0.0656 (9)	−0.0046 (6)	0.0065 (6)	0.0004 (7)
S2	0.0371 (6)	0.0574 (8)	0.0524 (8)	0.0102 (6)	0.0075 (6)	0.0128 (7)
O1	0.036 (2)	0.091 (3)	0.077 (3)	−0.005 (2)	0.019 (2)	0.008 (2)
O2	0.055 (2)	0.066 (3)	0.065 (3)	−0.024 (2)	0.005 (2)	−0.002 (2)
O3	0.0407 (19)	0.062 (2)	0.046 (2)	0.0168 (17)	0.0056 (16)	0.0084 (18)
O4	0.0347 (18)	0.059 (2)	0.0410 (19)	0.0012 (16)	0.0013 (16)	−0.0055 (16)
C1	0.031 (3)	0.041 (3)	0.043 (3)	0.006 (2)	−0.009 (2)	0.011 (2)
C2	0.028 (2)	0.045 (3)	0.042 (3)	−0.003 (2)	−0.002 (2)	0.009 (2)
C3	0.034 (3)	0.055 (4)	0.066 (4)	−0.003 (2)	0.007 (3)	0.013 (3)
C4	0.058 (4)	0.043 (3)	0.083 (4)	−0.018 (3)	−0.006 (3)	0.005 (3)
C5	0.069 (4)	0.052 (3)	0.076 (4)	−0.005 (3)	0.005 (4)	−0.006 (3)
C6	0.042 (3)	0.061 (4)	0.057 (3)	0.006 (3)	0.009 (3)	0.006 (3)
C7	0.026 (3)	0.061 (4)	0.055 (3)	−0.005 (3)	−0.002 (3)	0.017 (3)
C8	0.040 (3)	0.031 (2)	0.036 (3)	0.008 (2)	−0.004 (2)	−0.011 (2)
C9	0.037 (3)	0.039 (3)	0.042 (3)	0.004 (2)	0.000 (2)	0.000 (2)
C10	0.039 (3)	0.069 (4)	0.068 (4)	0.006 (3)	−0.006 (3)	0.016 (3)
C11	0.055 (4)	0.066 (4)	0.068 (4)	0.015 (3)	−0.014 (3)	0.019 (3)
C12	0.069 (4)	0.052 (3)	0.046 (3)	0.007 (3)	−0.009 (3)	0.014 (3)
C13	0.052 (3)	0.040 (3)	0.041 (3)	0.000 (2)	0.006 (3)	−0.001 (2)
C14	0.036 (2)	0.031 (2)	0.031 (3)	0.001 (2)	−0.002 (2)	−0.007 (2)

Geometric parameters (Å, º)

N1—C15	1.443 (6)	C27—H27B	0.9700
N1—H1A	0.8900	S1—C2	1.788 (5)
N1—H1B	0.8900	S1—S2	2.0480 (17)
N1—H1C	0.8900	S2—C9	1.795 (5)
N2—C21	1.456 (5)	O1—C7	1.237 (6)
N2—H2A	0.8900	O2—C7	1.254 (7)
N2—H2B	0.8901	O3—C14	1.239 (5)
N2—H2C	0.8899	O4—C14	1.262 (5)
C15—C20	1.343 (7)	C1—C2	1.393 (6)
C15—C16	1.369 (7)	C1—C6	1.396 (7)
C16—C17	1.364 (9)	C1—C7	1.521 (7)
C16—H16	0.9300	C2—C3	1.392 (7)
C17—C18	1.367 (9)	C3—C4	1.357 (7)
C17—H17	0.9300	C3—H3	0.9300
C18—C19	1.366 (9)	C4—C5	1.396 (8)
C18—C27	1.532 (8)	C4—H4	0.9300
C19—C20	1.403 (9)	C5—C6	1.349 (7)
C19—H19	0.9300	C5—H5	0.9300
C20—H20	0.9300	C6—H6	0.9300
C21—C22	1.334 (7)	C8—C13	1.384 (7)
C21—C26	1.360 (7)	C8—C9	1.414 (6)
C22—C23	1.397 (8)	C8—C14	1.508 (6)
C22—H22	0.9300	C9—C10	1.373 (7)
C23—C24	1.362 (9)	C10—C11	1.377 (8)
C23—H23	0.9300	C10—H10	0.9300
C24—C25	1.385 (8)	C11—C12	1.358 (8)
C24—C27	1.504 (8)	C11—H11	0.9300
C25—C26	1.379 (7)	C12—C13	1.380 (7)
C25—H25	0.9300	C12—H12	0.9300
C26—H26	0.9300	C13—H13	0.9300
C27—H27A	0.9700
C15—N1—H1A	109.2	C24—C27—H27A	108.9
C15—N1—H1B	109.6	C18—C27—H27A	108.9
H1A—N1—H1B	109.5	C24—C27—H27B	108.9
C15—N1—H1C	109.6	C18—C27—H27B	108.9
H1A—N1—H1C	109.5	H27A—C27—H27B	107.7
H1B—N1—H1C	109.5	C2—S1—S2	104.89 (16)
C21—N2—H2A	109.3	C9—S2—S1	106.11 (16)
C21—N2—H2B	109.6	C2—C1—C6	119.5 (5)
H2A—N2—H2B	109.5	C2—C1—C7	122.7 (5)
C21—N2—H2C	109.6	C6—C1—C7	117.7 (5)
H2A—N2—H2C	109.5	C1—C2—C3	118.1 (5)
H2B—N2—H2C	109.5	C1—C2—S1	120.7 (4)
C20—C15—C16	119.2 (5)	C3—C2—S1	121.2 (4)
C20—C15—N1	121.6 (5)	C4—C3—C2	121.6 (5)
C16—C15—N1	119.2 (5)	C4—C3—H3	119.2
C17—C16—C15	120.1 (6)	C2—C3—H3	119.2
C17—C16—H16	119.9	C3—C4—C5	120.1 (5)
C15—C16—H16	119.9	C3—C4—H4	119.9
C16—C17—C18	121.7 (6)	C5—C4—H4	119.9
C16—C17—H17	119.1	C6—C5—C4	119.2 (6)
C18—C17—H17	119.1	C6—C5—H5	120.4
C17—C18—C19	118.2 (6)	C4—C5—H5	120.4
C17—C18—C27	121.1 (6)	C5—C6—C1	121.5 (5)
C19—C18—C27	120.7 (6)	C5—C6—H6	119.3
C18—C19—C20	119.8 (6)	C1—C6—H6	119.3
C18—C19—H19	120.1	O1—C7—O2	124.0 (5)
C20—C19—H19	120.1	O1—C7—C1	118.1 (6)
C15—C20—C19	120.9 (6)	O2—C7—C1	117.8 (5)
C15—C20—H20	119.6	C13—C8—C9	119.0 (4)
C19—C20—H20	119.6	C13—C8—C14	119.4 (5)
C22—C21—C26	120.9 (5)	C9—C8—C14	121.7 (4)
C22—C21—N2	120.0 (5)	C10—C9—C8	118.1 (5)
C26—C21—N2	119.1 (4)	C10—C9—S2	122.3 (4)
C21—C22—C23	119.2 (6)	C8—C9—S2	119.6 (4)
C21—C22—H22	120.4	C9—C10—C11	121.6 (5)
C23—C22—H22	120.4	C9—C10—H10	119.2
C24—C23—C22	121.8 (6)	C11—C10—H10	119.2
C24—C23—H23	119.1	C12—C11—C10	120.7 (5)
C22—C23—H23	119.1	C12—C11—H11	119.6
C23—C24—C25	117.4 (5)	C10—C11—H11	119.6
C23—C24—C27	121.5 (6)	C11—C12—C13	118.9 (5)
C25—C24—C27	121.0 (6)	C11—C12—H12	120.5
C26—C25—C24	120.5 (5)	C13—C12—H12	120.5
C26—C25—H25	119.7	C12—C13—C8	121.6 (5)
C24—C25—H25	119.7	C12—C13—H13	119.2
C21—C26—C25	120.1 (5)	C8—C13—H13	119.2
C21—C26—H26	119.9	O3—C14—O4	124.0 (4)
C25—C26—H26	119.9	O3—C14—C8	118.7 (4)
C24—C27—C18	113.5 (5)	O4—C14—C8	117.3 (4)
C20—C15—C16—C17	3.2 (10)	S2—S1—C2—C3	18.8 (4)
N1—C15—C16—C17	−179.2 (6)	C1—C2—C3—C4	0.0 (8)
C15—C16—C17—C18	−2.6 (12)	S1—C2—C3—C4	178.6 (4)
C16—C17—C18—C19	1.6 (11)	C2—C3—C4—C5	0.6 (9)
C16—C17—C18—C27	−178.1 (6)	C3—C4—C5—C6	0.3 (9)
C17—C18—C19—C20	−1.4 (9)	C4—C5—C6—C1	−1.8 (9)
C27—C18—C19—C20	178.3 (5)	C2—C1—C6—C5	2.5 (8)
C16—C15—C20—C19	−3.0 (9)	C7—C1—C6—C5	179.9 (5)
N1—C15—C20—C19	179.5 (5)	C2—C1—C7—O1	167.0 (5)
C18—C19—C20—C15	2.1 (9)	C6—C1—C7—O1	−10.3 (7)
C26—C21—C22—C23	0.3 (9)	C2—C1—C7—O2	−10.9 (7)
N2—C21—C22—C23	−177.5 (5)	C6—C1—C7—O2	171.8 (5)
C21—C22—C23—C24	−1.6 (11)	C13—C8—C9—C10	1.2 (7)
C22—C23—C24—C25	1.8 (10)	C14—C8—C9—C10	−177.9 (5)
C22—C23—C24—C27	−177.2 (6)	C13—C8—C9—S2	−178.0 (4)
C23—C24—C25—C26	−0.9 (9)	C14—C8—C9—S2	2.8 (6)
C27—C24—C25—C26	178.2 (6)	S1—S2—C9—C10	2.4 (5)
C22—C21—C26—C25	0.6 (8)	S1—S2—C9—C8	−178.4 (3)
N2—C21—C26—C25	178.4 (5)	C8—C9—C10—C11	0.9 (8)
C24—C25—C26—C21	−0.3 (9)	S2—C9—C10—C11	−179.8 (4)
C23—C24—C27—C18	−105.1 (7)	C9—C10—C11—C12	−2.2 (9)
C25—C24—C27—C18	75.9 (8)	C10—C11—C12—C13	1.2 (9)
C17—C18—C27—C24	−112.8 (7)	C11—C12—C13—C8	1.0 (8)
C19—C18—C27—C24	67.5 (8)	C9—C8—C13—C12	−2.2 (7)
C2—S1—S2—C9	−86.2 (2)	C14—C8—C13—C12	177.0 (5)
C6—C1—C2—C3	−1.6 (7)	C13—C8—C14—O3	176.3 (4)
C7—C1—C2—C3	−178.8 (4)	C9—C8—C14—O3	−4.6 (6)
C6—C1—C2—S1	179.9 (4)	C13—C8—C14—O4	−4.2 (6)
C7—C1—C2—S1	2.7 (6)	C9—C8—C14—O4	174.9 (4)
S2—S1—C2—C1	−162.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.89	1.85	2.722 (6)	166
N1—H1B···O3^i	0.89	1.84	2.724 (5)	174
N1—H1C···O1^ii	0.89	1.89	2.753 (5)	163
N2—H2A···O4^iii	0.89	1.95	2.804 (5)	161
N2—H2B···O1^iv	0.89	2.03	2.834 (5)	150
N2—H2B···O2^iv	0.89	2.50	3.231 (5)	140
N2—H2C···O4	0.89	1.87	2.734 (5)	164

Symmetry codes: (i) −y+1, x, −z+1; (ii) y−1/2, x+1/2, z−1/2; (iii) −y+3/2, −x+3/2, z−1/2; (iv) y, −x+1, −z+1.