Diquino[3,4-b;4′,3′-e][1,4]dithiine

In the title compound, C₁₈H₁₀N₂S₂, a crystallographic mirror plane passes through the two S atoms. The penta­cyclic ring system is folded along the S—S vector and the central dithiine ring adopts a boat conformation.

Key indicators

• Single-crystal synchrotron study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.077
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      30.07 Deg.

Author Response: The beam was lost during the data collection, hampering the collection of the higher resolutions scans.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: The beam was lost during the data collection, hampering the collection of the higher resolutions scans.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Alert level G
  ABSMU_01  Radiation type not identified. Calculation of
            _exptl_absorpt_correction_mu not performed.
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           34.42
           From the CIF: _reflns_number_total               1157
           Count of symmetry unique reflns          856
           Completeness (_total/calc)            135.16%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       301
           Fraction of Friedel pairs measured     0.352
           Are heavy atom types Z>Si present        yes

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

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

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ATOMS (Dowty, 1994); software used to prepare material for publication: CRYSTALS and enCIFer (Allen et al., 2004).

Diquino[3,4 - b;4',3'-e][1,4]dithiine

Crystal data

C18H10N2S2	Dx = 1.488 Mg m^−3
Mr = 318.42	Synchrotron radiation, λ = 0.90200 Å
Orthorhombic, Pmn21	Cell parameters from 2883 reflections
a = 23.440 (5) Å	θ = 3.4–34.4°
b = 7.5873 (15) Å	µ = 0.37 mm^−1
c = 3.9960 (8) Å	T = 293 K
V = 710.7 (3) Å^3	Needle, colourless
Z = 2	0.2 × 0.01 × 0.01 mm
F(000) = 328

Data collection

Siemens SMART CCD diffractometer	1157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
ω scans	θmax = 34.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −24→28
Tmin = 0.85, Tmax = 0.97	k = −9→9
2883 measured reflections	l = −4→4
1157 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = [1-(Fo-Fc)^2/36σ^2(F)]^2/[15.6T0(x) + 20.5T1(x) + 8.37T2(x)] where Ti are Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994)
wR(F^2) = 0.077	(Δ/σ)max = 0.000138
S = 0.96	Δρmax = 0.19 e Å^−3
1157 reflections	Δρmin = −0.18 e Å^−3
104 parameters	Absolute structure: Flack (1983), 497 Friedel pairs
1 restraint	Absolute structure parameter: −0.11 (14)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
N	−0.15247 (9)	0.4208 (3)	0.6446 (7)	0.0435
C2	−0.10638 (12)	0.3623 (4)	0.5018 (8)	0.0408
C3	−0.05795 (10)	0.4654 (3)	0.4219 (7)	0.0339
C4	−0.05805 (10)	0.6406 (3)	0.5055 (7)	0.0319
C5	−0.10680 (10)	0.7126 (3)	0.6734 (7)	0.0323
C6	−0.11129 (11)	0.8900 (4)	0.7789 (7)	0.0401
C7	−0.16039 (12)	0.9493 (4)	0.9317 (9)	0.0467
C8	−0.20638 (12)	0.8357 (5)	0.9834 (9)	0.0513
C9	−0.20308 (11)	0.6637 (4)	0.8901 (9)	0.0469
C10	−0.15341 (11)	0.5955 (4)	0.7340 (7)	0.0373
S2	0.0000	0.77991 (13)	0.4020 (3)	0.0383
S1	0.0000	0.36432 (15)	0.2145 (3)	0.0431
H21	−0.1056	0.2463	0.3932	0.0591*
H61	−0.0803	0.9625	0.6864	0.0568*
H71	−0.1628	1.0667	0.9585	0.0671*
H81	−0.2392	0.8795	1.0381	0.0733*
H91	−0.2338	0.5876	0.8783	0.0680*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0352 (12)	0.0469 (13)	0.0485 (17)	−0.0113 (10)	−0.0044 (11)	0.0064 (12)
C2	0.0426 (15)	0.0398 (15)	0.0400 (19)	−0.0075 (12)	−0.0075 (13)	0.0032 (12)
C3	0.0342 (11)	0.0387 (12)	0.0288 (15)	−0.0019 (10)	−0.0086 (11)	0.0043 (12)
C4	0.0261 (11)	0.0376 (13)	0.0318 (15)	−0.0006 (10)	−0.0062 (10)	0.0102 (11)
C5	0.0252 (11)	0.0408 (14)	0.0309 (15)	0.0001 (10)	−0.0065 (10)	0.0099 (12)
C6	0.0318 (12)	0.0438 (15)	0.045 (2)	0.0030 (11)	−0.0082 (12)	0.0060 (14)
C7	0.0421 (14)	0.0516 (17)	0.0463 (19)	0.0090 (12)	−0.0072 (15)	−0.0048 (16)
C8	0.0363 (14)	0.075 (2)	0.043 (2)	0.0099 (14)	0.0024 (13)	−0.0014 (16)
C9	0.0294 (12)	0.0676 (19)	0.0436 (19)	−0.0061 (12)	−0.0016 (13)	0.0051 (18)
C10	0.0310 (13)	0.0479 (15)	0.0332 (17)	−0.0064 (11)	−0.0082 (12)	0.0077 (15)
S2	0.0274 (4)	0.0362 (4)	0.0512 (6)	0.0000	0.0000	0.0185 (5)
S1	0.0453 (5)	0.0470 (5)	0.0371 (6)	0.0000	0.0000	−0.0074 (5)

Geometric parameters (Å, º)

N—C2	1.300 (4)	C5—C10	1.429 (3)
N—C10	1.373 (4)	C6—C7	1.378 (4)
C2—C3	1.416 (4)	C6—H61	0.984
C2—H21	0.981	C7—C8	1.396 (4)
C3—C4	1.371 (4)	C7—H71	0.899
C3—S1	1.766 (3)	C8—C9	1.359 (5)
C4—C5	1.433 (4)	C8—H81	0.867
C4—S2	1.772 (3)	C9—C10	1.419 (4)
C5—C6	1.414 (4)	C9—H91	0.925
C2—N—C10	117.2 (2)	C7—C6—H61	126.9
N—C2—C3	125.2 (3)	C6—C7—C8	120.6 (3)
N—C2—H21	121.1	C6—C7—H71	115.4
C3—C2—H21	112.4	C8—C7—H71	123.0
C2—C3—C4	118.7 (3)	C7—C8—C9	120.5 (3)
C2—C3—S1	118.8 (2)	C7—C8—H81	119.1
C4—C3—S1	122.5 (2)	C9—C8—H81	119.2
C3—C4—C5	119.0 (2)	C8—C9—C10	121.2 (3)
C3—C4—S2	121.3 (2)	C8—C9—H91	124.7
C5—C4—S2	119.6 (2)	C10—C9—H91	112.9
C4—C5—C6	124.2 (2)	C5—C10—C9	118.4 (3)
C4—C5—C10	116.9 (2)	C5—C10—N	123.0 (3)
C6—C5—C10	119.0 (3)	C9—C10—N	118.7 (2)
C5—C6—C7	120.3 (3)	C4^i—S2—C4	100.34 (16)
C5—C6—H61	111.4	C3—S1—C3^i	100.52 (18)

Symmetry code: (i) −x, y, z.