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The title compound, C6H16N2·2C6H7NO3S, consists of a strongly hydrogen-bonded adduct of N,N,N',N'-tetra­methyl­ethane-1,2-diamine (tmen) and undissociated N-hydroxy­benzensulfonamide (Piloty's acid, PA). The diamine mol­ecule sits on a center of symmetry at the mid-point of the central C-C bond. The C-S-N-O linkage in PA adopts a syn geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009658/sj2229sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009658/sj2229Isup2.hkl
Contains datablock I

CCDC reference: 643097

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.094
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _diffrn_reflns_theta_full 25.01 From the CIF: _reflns_number_total 1613 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2071 Completeness (_total/calc) 77.89%
Author Response: Data collected with an old version of the data collection software (XSCANS Ver. 2.20) and with a low temperature arm which limited the data collection range.
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.78
Author Response: Data collected with an old version of the data collection software (XSCANS Ver. 2.20) and with a low temperature arm which limited the data collection range.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.78
Author Response: Data collected with an old version of the data collection software (XSCANS Ver. 2.20) and with a low temperature arm which limited the data collection range.

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - O3 .. 12.76 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1613 From the CIF: _diffrn_reflns_limit_ max hkl 6. 1. 32. From the CIF: _diffrn_reflns_limit_ min hkl -1. -6. -32. TEST1: Expected hkl limits for theta max Calculated maximum hkl 9. 6. 32. Calculated minimum hkl -9. -6. -32.
Author Response: Data collected with an old version of the data collection software (XSCANS Ver. 2.20) and with a low temperature arm which limited the data collection range.

3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1996); software used to prepare material for publication: SHELXTL.

N,N,N',N'-Tetramethylethane-1,2-diamine–N-hydroxybenzensulfonamide (1/2) top
Crystal data top
C6H16N2·2C6H7NO3SF(000) = 492
Mr = 462.58Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 35 reflections
a = 8.1452 (15) Åθ = 4.6–12.5°
b = 5.3296 (9) ŵ = 0.27 mm1
c = 27.203 (4) ÅT = 173 K
β = 96.268 (10)°Rectangular prism, colorless
V = 1173.8 (3) Å30.34 × 0.20 × 0.18 mm
Z = 2
Data collection top
Bruker P4
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.5°
Graphite monochromatorh = 16
ω scansk = 61
2534 measured reflectionsl = 3232
1613 independent reflections3 standard reflections every 97 reflections
1160 reflections with I > 2σ(I) intensity decay: 1%
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0404P)2]
where P = (Fo2 + 2Fc2)/3
1613 reflections(Δ/σ)max = 0.002
144 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. The crystal used for the X-ray data collection was enveloped with Paratone N oil, and the data collection was carried out at -100

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*/Ueq
O10.0077 (3)0.6642 (4)0.11692 (6)0.0610 (7)
H1O0.047 (4)0.753 (6)0.0913 (11)0.082 (10)*
N10.1713 (4)0.6343 (5)0.10623 (8)0.0498 (7)
H1N0.209 (4)0.496 (6)0.1143 (9)0.053 (10)*
S10.29587 (11)0.84468 (13)0.13438 (2)0.0470 (3)
O20.2432 (3)1.0814 (3)0.11392 (6)0.0652 (6)
O30.4586 (3)0.7539 (4)0.12923 (6)0.0667 (6)
C10.2663 (3)0.8527 (5)0.19763 (8)0.0373 (7)
C20.1742 (4)1.0400 (5)0.21564 (9)0.0498 (8)
H2B0.12301.15990.19430.060*
C30.1578 (4)1.0496 (6)0.26540 (10)0.0619 (9)
H3B0.09611.17690.27790.074*
C40.2320 (4)0.8724 (6)0.29638 (9)0.0620 (9)
H4A0.22190.88130.33010.074*
C50.3209 (4)0.6822 (6)0.27871 (9)0.0578 (8)
H5A0.36880.56000.30010.069*
C60.3397 (3)0.6718 (5)0.22859 (9)0.0499 (7)
H6A0.40110.54400.21620.060*
N20.1577 (3)0.9319 (4)0.04428 (7)0.0474 (6)
C70.0576 (3)1.0807 (5)0.01321 (8)0.0476 (8)
H7A0.00691.20200.03370.057*
H7B0.13031.17250.01110.057*
C80.2432 (4)1.1003 (6)0.07525 (11)0.0788 (11)
H8A0.16391.20260.09470.118*
H8B0.30451.00330.09670.118*
H8C0.31751.20560.05470.118*
C90.2799 (4)0.7771 (6)0.01449 (10)0.0671 (9)
H9A0.22440.66590.00600.101*
H9B0.35380.88360.00600.101*
H9C0.34160.68070.03600.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0556 (19)0.0747 (15)0.0506 (10)0.0181 (13)0.0028 (11)0.0188 (11)
N10.059 (2)0.0433 (15)0.0454 (11)0.0073 (15)0.0001 (12)0.0025 (12)
S10.0583 (7)0.0424 (4)0.0406 (3)0.0100 (4)0.0064 (3)0.0056 (3)
O20.0989 (18)0.0426 (11)0.0526 (10)0.0136 (12)0.0019 (11)0.0128 (9)
O30.0452 (16)0.0920 (16)0.0661 (12)0.0021 (14)0.0210 (10)0.0018 (12)
C10.0358 (19)0.0342 (13)0.0414 (11)0.0036 (14)0.0021 (12)0.0037 (12)
C20.051 (2)0.0407 (15)0.0574 (15)0.0045 (16)0.0051 (14)0.0071 (13)
C30.072 (3)0.0555 (18)0.0612 (16)0.0039 (19)0.0208 (16)0.0105 (16)
C40.068 (3)0.076 (2)0.0432 (13)0.008 (2)0.0095 (15)0.0007 (16)
C50.058 (2)0.065 (2)0.0489 (14)0.0040 (19)0.0014 (14)0.0213 (15)
C60.046 (2)0.0488 (16)0.0553 (14)0.0053 (16)0.0076 (13)0.0035 (13)
N20.0432 (17)0.0563 (14)0.0439 (11)0.0032 (13)0.0100 (11)0.0031 (11)
C70.054 (2)0.0496 (16)0.0397 (12)0.0027 (15)0.0075 (12)0.0030 (11)
C80.089 (3)0.080 (2)0.0748 (18)0.011 (2)0.0413 (19)0.0147 (18)
C90.057 (2)0.073 (2)0.0708 (17)0.0115 (19)0.0040 (16)0.0031 (17)
Geometric parameters (Å, º) top
O1—N11.404 (3)C5—C61.389 (3)
O1—H1O0.92 (3)C5—H5A0.9300
N1—S11.644 (2)C6—H6A0.9300
N1—H1N0.82 (3)N2—C71.469 (3)
S1—O21.4259 (18)N2—C81.459 (3)
S1—O31.432 (2)N2—C91.467 (3)
S1—C11.764 (2)C7—C7i1.511 (5)
C1—C21.371 (3)C7—H7A0.9700
C1—C61.374 (3)C7—H7B0.9700
C2—C31.376 (3)C8—H8A0.9600
C2—H2B0.9300C8—H8B0.9600
C3—C41.363 (4)C8—H8C0.9600
C3—H3B0.9300C9—H9A0.9600
C4—C51.364 (4)C9—H9B0.9600
C4—H4A0.9300C9—H9C0.9600
N1—O1—H1O107.3 (19)C1—C6—C5119.1 (3)
O1—N1—S1112.2 (2)C1—C6—H6A120.4
O1—N1—H1N113 (2)C5—C6—H6A120.4
S1—N1—H1N107 (2)C7—N2—C8109.3 (2)
O2—S1—O3120.21 (13)C7—N2—C9111.81 (19)
O2—S1—N1106.10 (14)C8—N2—C9109.1 (2)
O3—S1—N1104.74 (16)N2—C7—C7i112.3 (3)
O2—S1—C1106.97 (12)N2—C7—H7A109.2
O3—S1—C1109.27 (11)C7i—C7—H7A109.2
N1—S1—C1109.15 (12)N2—C7—H7B109.2
C2—C1—C6120.7 (2)C7i—C7—H7B109.2
C2—C1—S1120.32 (19)H7A—C7—H7B107.9
C6—C1—S1119.0 (2)N2—C8—H8A109.5
C1—C2—C3119.6 (3)N2—C8—H8B109.5
C1—C2—H2B120.2H8A—C8—H8B109.5
C3—C2—H2B120.2N2—C8—H8C109.5
C4—C3—C2119.9 (3)H8A—C8—H8C109.5
C4—C3—H3B120.1H8B—C8—H8C109.5
C2—C3—H3B120.1N2—C9—H9A109.5
C5—C4—C3121.0 (2)N2—C9—H9B109.5
C5—C4—H4A119.5H9A—C9—H9B109.5
C3—C4—H4A119.5N2—C9—H9C109.5
C4—C5—C6119.7 (3)H9A—C9—H9C109.5
C4—C5—H5A120.2H9B—C9—H9C109.5
C6—C5—H5A120.2
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N20.92 (3)1.76 (3)2.678 (3)177 (3)
N1—H1N···O2ii0.82 (3)2.23 (3)3.007 (3)159 (3)
Symmetry code: (ii) x, y1, z.
 

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