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The crystal structure of the title salt, C6H18N22+·2C7H4NO3S, contains two crystallographically independent hexa­methyl­ene­dia­mmonium dications and two independent saccharinate anions; each of the dications occupies a special position on an inversion centre. The extensive hydrogen-bonding system, involving all six `active' H atoms, links the anions and cations into an infinite three-dimensional supramolecular assembly.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008051/ya6280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008051/ya6280Isup2.hkl
Contains datablock I

CCDC reference: 605225

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 77%
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.163
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact C19' .. C20' .. 2.51 Ang.
Author Response: This is due to serious disorder for C19, C20. We have tried to use distance constraints to refine the structure, but the obtained results are still not satisfactory.
PLAT432_ALERT_2_A Short Inter X...Y Contact  C20'   ..  C20'    ..       2.06 Ang.
Author Response: This is due to serious disorder for C19, C20. We have tried to use distance constraints to refine the structure, but the obtained results are still not satisfactory.
PLAT432_ALERT_2_A Short Inter X...Y Contact  C19    ..  C20     ..       2.65 Ang.
Author Response: This is due to serious disorder for C19, C20. We have tried to use distance constraints to refine the structure, but the obtained results are still not satisfactory.
PLAT432_ALERT_2_A Short Inter X...Y Contact  C20    ..  C20     ..       2.25 Ang.
Author Response: This is due to serious disorder for C19, C20. We have tried to use distance constraints to refine the structure, but the obtained results are still not satisfactory.

Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.285 Value of mu given = 0.280 CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.99 <> 1.01 Calculated formula weight = 482.5686 Formula weight given = 476.5200 CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -P 2yc PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.70 Deg. C19' -C18 -C19 1.555 1.555 1.555
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H26 N4 O6 S2 Atom count from the _atom_site data: C20 H20 N4 O6 S2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C20 H26 N4 O6 S2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.00 0.00 H 104.00 80.00 24.00 N 16.00 16.00 0.00 O 24.00 24.00 0.00 S 8.00 8.00 0.00
4 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; 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.

Hexamethylenediammonium bis(saccharinate) top
Crystal data top
C6H18N22+·2C7H4NO3SF(000) = 992
Mr = 476.52Dx = 1.423 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 3509 reflections
a = 11.4799 (10) Åθ = 2.4–26.9°
b = 11.5301 (10) ŵ = 0.28 mm1
c = 16.9116 (15) ÅT = 292 K
β = 96.499 (2)°Irregular, colorless
V = 2224.1 (3) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω scansh = 1113
10895 measured reflectionsk = 1313
3907 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0922P)2 + 0.7478P]
where P = (Fo2 + 2Fc2)/3
3907 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.43 e Å3
2 restraintsΔρmin = 0.37 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.28704 (6)0.22357 (6)0.17581 (4)0.0412 (2)
S20.78835 (6)0.25518 (6)0.17968 (4)0.0392 (2)
C10.2751 (2)0.2410 (2)0.07138 (15)0.0394 (6)
C20.3347 (2)0.1881 (2)0.01388 (16)0.0503 (7)
H20.39230.13260.02720.060*
C30.3039 (3)0.2221 (3)0.06386 (18)0.0604 (8)
H30.34160.18840.10400.072*
C40.2181 (3)0.3052 (3)0.08382 (17)0.0568 (8)
H40.19990.32660.13680.068*
C50.1593 (2)0.3567 (2)0.02559 (15)0.0470 (7)
H50.10110.41170.03880.056*
C60.1901 (2)0.3237 (2)0.05273 (14)0.0393 (6)
C70.1417 (2)0.3672 (2)0.12581 (15)0.0418 (6)
C80.7712 (2)0.2582 (2)0.07443 (15)0.0365 (6)
C90.8287 (2)0.3213 (2)0.02082 (16)0.0460 (6)
H90.88710.37460.03780.055*
C100.7950 (3)0.3013 (3)0.05916 (17)0.0538 (7)
H100.83050.34300.09690.065*
C110.7095 (3)0.2205 (2)0.08420 (16)0.0520 (7)
H110.68900.20870.13840.062*
C120.6544 (2)0.1572 (2)0.02989 (15)0.0440 (6)
H120.59730.10260.04680.053*
C130.6863 (2)0.1772 (2)0.05023 (14)0.0359 (5)
C140.6419 (2)0.1190 (2)0.12024 (14)0.0403 (6)
C150.5272 (3)1.0239 (2)0.31722 (15)0.0500 (7)
H15A0.51451.10700.31300.060*
H15B0.61101.01000.32420.060*
C160.4733 (2)0.9778 (3)0.38790 (15)0.0505 (7)
H16A0.39050.99700.38200.061*
H16B0.48000.89390.38860.061*
C170.5283 (3)1.0241 (3)0.46506 (16)0.0540 (7)
H17A0.52171.10800.46480.065*
H17B0.61111.00460.47150.065*
C180.0348 (3)0.9343 (3)0.16999 (16)0.0698 (9)
N10.1905 (2)0.3163 (2)0.19324 (13)0.0503 (6)
N20.6929 (2)0.1574 (2)0.19098 (12)0.0492 (6)
N30.4750 (2)0.9674 (2)0.24465 (12)0.0485 (6)
H3A0.48770.89130.24840.073*
H3B0.50730.99540.20320.073*
H3C0.39820.98090.23810.073*
N40.0226 (2)1.0030 (2)0.23799 (14)0.0547 (6)
H4A0.09940.98960.24330.082*
H4B0.00670.98230.28240.082*
H4C0.00941.07810.22890.082*
O10.25375 (17)0.10747 (17)0.19689 (12)0.0596 (6)
O20.40253 (17)0.25549 (17)0.21210 (12)0.0542 (5)
O30.06501 (17)0.44393 (17)0.12222 (11)0.0517 (5)
O40.75719 (16)0.36500 (17)0.21238 (11)0.0535 (5)
O50.90521 (16)0.21865 (17)0.20921 (11)0.0537 (5)
O60.56570 (17)0.04207 (16)0.11148 (11)0.0508 (5)
C190.0157 (8)0.9956 (11)0.0983 (5)0.054 (2)0.489 (10)
C200.0119 (7)1.0490 (8)0.0559 (5)0.071 (3)0.489 (10)
C19'0.0190 (9)0.9368 (12)0.0904 (5)0.076 (3)0.511 (10)
C20'0.0416 (6)0.9336 (8)0.0262 (4)0.080 (3)0.511 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0401 (4)0.0421 (4)0.0411 (4)0.0046 (3)0.0037 (3)0.0081 (3)
S20.0384 (4)0.0401 (4)0.0384 (4)0.0038 (3)0.0010 (3)0.0069 (2)
C10.0405 (15)0.0360 (13)0.0417 (14)0.0026 (11)0.0044 (11)0.0015 (10)
C20.0473 (16)0.0504 (16)0.0548 (17)0.0061 (13)0.0122 (13)0.0021 (13)
C30.066 (2)0.070 (2)0.0478 (17)0.0027 (17)0.0180 (15)0.0105 (14)
C40.070 (2)0.0609 (18)0.0401 (15)0.0010 (16)0.0071 (14)0.0017 (13)
C50.0544 (17)0.0457 (15)0.0403 (14)0.0022 (13)0.0024 (12)0.0025 (12)
C60.0411 (14)0.0359 (13)0.0411 (14)0.0025 (11)0.0054 (11)0.0018 (10)
C70.0399 (14)0.0437 (14)0.0424 (14)0.0027 (12)0.0069 (11)0.0050 (11)
C80.0386 (14)0.0326 (12)0.0380 (14)0.0042 (10)0.0035 (11)0.0026 (10)
C90.0426 (15)0.0390 (14)0.0575 (17)0.0039 (12)0.0109 (12)0.0005 (12)
C100.0607 (19)0.0554 (17)0.0484 (17)0.0015 (15)0.0198 (14)0.0081 (13)
C110.0642 (19)0.0577 (17)0.0349 (14)0.0012 (15)0.0096 (13)0.0012 (12)
C120.0466 (15)0.0450 (14)0.0400 (14)0.0038 (12)0.0029 (11)0.0058 (11)
C130.0377 (13)0.0330 (12)0.0376 (13)0.0031 (10)0.0069 (10)0.0005 (10)
C140.0407 (14)0.0410 (14)0.0399 (14)0.0019 (11)0.0070 (11)0.0011 (11)
C150.0527 (17)0.0545 (16)0.0431 (15)0.0012 (13)0.0062 (12)0.0057 (12)
C160.0478 (16)0.0584 (17)0.0466 (16)0.0007 (13)0.0105 (12)0.0018 (12)
C170.0493 (17)0.0655 (19)0.0485 (16)0.0033 (14)0.0116 (13)0.0006 (14)
C180.073 (2)0.101 (3)0.0352 (15)0.003 (2)0.0046 (14)0.0073 (16)
N10.0501 (14)0.0644 (15)0.0370 (12)0.0061 (12)0.0072 (10)0.0024 (11)
N20.0526 (14)0.0592 (14)0.0356 (12)0.0081 (12)0.0042 (10)0.0012 (10)
N30.0511 (14)0.0529 (13)0.0425 (12)0.0007 (11)0.0088 (10)0.0043 (10)
N40.0516 (14)0.0572 (14)0.0576 (14)0.0110 (12)0.0160 (11)0.0160 (12)
O10.0558 (12)0.0525 (12)0.0702 (13)0.0110 (10)0.0058 (10)0.0236 (10)
O20.0455 (12)0.0574 (12)0.0567 (12)0.0068 (9)0.0077 (9)0.0070 (9)
O30.0525 (12)0.0528 (11)0.0497 (11)0.0099 (9)0.0055 (9)0.0065 (9)
O40.0550 (12)0.0513 (11)0.0531 (11)0.0089 (9)0.0015 (9)0.0196 (9)
O50.0448 (11)0.0556 (12)0.0572 (12)0.0090 (9)0.0089 (9)0.0066 (9)
O60.0528 (11)0.0520 (11)0.0479 (11)0.0153 (9)0.0068 (9)0.0013 (9)
C190.071 (5)0.053 (5)0.043 (4)0.015 (5)0.024 (4)0.020 (4)
C200.075 (5)0.079 (6)0.061 (5)0.017 (4)0.025 (4)0.012 (4)
C19'0.102 (6)0.075 (7)0.051 (5)0.034 (6)0.007 (4)0.004 (5)
C20'0.081 (5)0.127 (7)0.034 (4)0.028 (5)0.018 (3)0.005 (4)
Geometric parameters (Å, º) top
S1—O21.4442 (19)C11—H110.9300
S1—O11.4477 (19)C12—C131.383 (3)
S1—N11.591 (2)C12—H120.9300
S1—C11.767 (3)C13—C141.499 (3)
S2—O51.4403 (19)C14—O61.243 (3)
S2—O41.4429 (18)C14—N21.346 (3)
S2—N21.598 (2)C15—N31.457 (3)
S2—C81.769 (3)C15—C161.504 (4)
C1—C61.376 (4)C15—H15A0.9700
C1—C21.391 (4)C15—H15B0.9700
C2—C31.379 (4)C16—C171.483 (4)
C2—H20.9300C16—H16A0.9700
C3—C41.387 (4)C16—H16B0.9700
C3—H30.9300C17—C17i1.518 (5)
C4—C51.389 (4)C17—H17A0.9700
C4—H40.9300C17—H17B0.9700
C5—C61.385 (3)C18—N41.488 (4)
C5—H50.9300C18—C19'1.544 (7)
C6—C71.498 (3)C18—C191.571 (6)
C7—O31.245 (3)N3—H3A0.8900
C7—N11.347 (3)N3—H3B0.8900
C8—C131.378 (3)N3—H3C0.8900
C8—C91.387 (4)N4—H4A0.8900
C9—C101.384 (4)N4—H4B0.8900
C9—H90.9300N4—H4C0.8900
C10—C111.384 (4)C19—C200.970 (10)
C10—H100.9300C19'—C20'1.223 (12)
C11—C121.382 (4)C20—C20'ii1.593 (12)
O2—S1—O1112.72 (12)C11—C12—H12120.9
O2—S1—N1112.05 (13)C13—C12—H12120.9
O1—S1—N1111.51 (12)C8—C13—C12120.3 (2)
O2—S1—C1111.04 (12)C8—C13—C14111.2 (2)
O1—S1—C1111.01 (12)C12—C13—C14128.5 (2)
N1—S1—C197.59 (11)O6—C14—N2124.8 (2)
O5—S2—O4112.66 (11)O6—C14—C13121.5 (2)
O5—S2—N2112.11 (12)N2—C14—C13113.7 (2)
O4—S2—N2111.73 (12)N3—C15—C16110.1 (2)
O5—S2—C8110.34 (12)N3—C15—H15A109.6
O4—S2—C8111.37 (11)C16—C15—H15A109.6
N2—S2—C897.72 (11)N3—C15—H15B109.6
C6—C1—C2122.4 (2)C16—C15—H15B109.6
C6—C1—S1106.28 (18)H15A—C15—H15B108.1
C2—C1—S1131.3 (2)C17—C16—C15113.5 (2)
C3—C2—C1116.7 (3)C17—C16—H16A108.9
C3—C2—H2121.7C15—C16—H16A108.9
C1—C2—H2121.7C17—C16—H16B108.9
C2—C3—C4121.8 (3)C15—C16—H16B108.9
C2—C3—H3119.1H16A—C16—H16B107.7
C4—C3—H3119.1C16—C17—C17i112.1 (3)
C3—C4—C5120.7 (3)C16—C17—H17A109.2
C3—C4—H4119.6C17i—C17—H17A109.2
C5—C4—H4119.6C16—C17—H17B109.2
C6—C5—C4118.0 (3)C17i—C17—H17B109.2
C6—C5—H5121.0H17A—C17—H17B107.9
C4—C5—H5121.0N4—C18—C19'118.6 (6)
C1—C6—C5120.5 (2)N4—C18—C19100.8 (5)
C1—C6—C7111.3 (2)C19'—C18—C1925.7 (3)
C5—C6—C7128.3 (2)C7—N1—S1111.58 (17)
O3—C7—N1125.1 (2)C14—N2—S2111.15 (17)
O3—C7—C6121.6 (2)C15—N3—H3A109.5
N1—C7—C6113.3 (2)C15—N3—H3B109.5
C13—C8—C9122.3 (2)H3A—N3—H3B109.5
C13—C8—S2106.25 (18)C15—N3—H3C109.5
C9—C8—S2131.4 (2)H3A—N3—H3C109.5
C10—C9—C8116.8 (2)H3B—N3—H3C109.5
C10—C9—H9121.6C18—N4—H4A109.5
C8—C9—H9121.6C18—N4—H4B109.5
C9—C10—C11121.5 (3)H4A—N4—H4B109.5
C9—C10—H10119.3C18—N4—H4C109.5
C11—C10—H10119.3H4A—N4—H4C109.5
C12—C11—C10121.0 (3)H4B—N4—H4C109.5
C12—C11—H11119.5C20—C19—C18137.6 (10)
C10—C11—H11119.5C20'—C19'—C18122.0 (9)
C11—C12—C13118.2 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2iii0.892.072.872 (3)149
N3—H3B···O6iv0.891.842.726 (3)174
N3—H3C···O4iii0.892.453.077 (3)128
N3—H3C···O1iv0.892.263.041 (3)147
N4—H4A···O1iv0.892.433.065 (3)128
N4—H4A···O4iii0.892.253.024 (3)146
N4—H4B···O3v0.891.872.757 (3)178
N4—H4C···O5vi0.892.022.844 (3)154
Symmetry codes: (iii) x+1, y+1/2, z+1/2; (iv) x, y+1, z; (v) x, y+1/2, z+1/2; (vi) x1, y+1, z.
 

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