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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
CCDC reference: 643097
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C6H16N2·2C6H7NO3S | F(000) = 492 |
Mr = 462.58 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 35 reflections |
a = 8.1452 (15) Å | θ = 4.6–12.5° |
b = 5.3296 (9) Å | µ = 0.27 mm−1 |
c = 27.203 (4) Å | T = 173 K |
β = 96.268 (10)° | Rectangular prism, colorless |
V = 1173.8 (3) Å3 | 0.34 × 0.20 × 0.18 mm |
Z = 2 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.029 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = −1→6 |
ω scans | k = −6→1 |
2534 measured reflections | l = −32→32 |
1613 independent reflections | 3 standard reflections every 97 reflections |
1160 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H 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 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0077 (3) | 0.6642 (4) | 0.11692 (6) | 0.0610 (7) | |
H1O | −0.047 (4) | 0.753 (6) | 0.0913 (11) | 0.082 (10)* | |
N1 | 0.1713 (4) | 0.6343 (5) | 0.10623 (8) | 0.0498 (7) | |
H1N | 0.209 (4) | 0.496 (6) | 0.1143 (9) | 0.053 (10)* | |
S1 | 0.29587 (11) | 0.84468 (13) | 0.13438 (2) | 0.0470 (3) | |
O2 | 0.2432 (3) | 1.0814 (3) | 0.11392 (6) | 0.0652 (6) | |
O3 | 0.4586 (3) | 0.7539 (4) | 0.12923 (6) | 0.0667 (6) | |
C1 | 0.2663 (3) | 0.8527 (5) | 0.19763 (8) | 0.0373 (7) | |
C2 | 0.1742 (4) | 1.0400 (5) | 0.21564 (9) | 0.0498 (8) | |
H2B | 0.1230 | 1.1599 | 0.1943 | 0.060* | |
C3 | 0.1578 (4) | 1.0496 (6) | 0.26540 (10) | 0.0619 (9) | |
H3B | 0.0961 | 1.1769 | 0.2779 | 0.074* | |
C4 | 0.2320 (4) | 0.8724 (6) | 0.29638 (9) | 0.0620 (9) | |
H4A | 0.2219 | 0.8813 | 0.3301 | 0.074* | |
C5 | 0.3209 (4) | 0.6822 (6) | 0.27871 (9) | 0.0578 (8) | |
H5A | 0.3688 | 0.5600 | 0.3001 | 0.069* | |
C6 | 0.3397 (3) | 0.6718 (5) | 0.22859 (9) | 0.0499 (7) | |
H6A | 0.4011 | 0.5440 | 0.2162 | 0.060* | |
N2 | −0.1577 (3) | 0.9319 (4) | 0.04428 (7) | 0.0474 (6) | |
C7 | −0.0576 (3) | 1.0807 (5) | 0.01321 (8) | 0.0476 (8) | |
H7A | 0.0069 | 1.2020 | 0.0337 | 0.057* | |
H7B | −0.1303 | 1.1725 | −0.0111 | 0.057* | |
C8 | −0.2432 (4) | 1.1003 (6) | 0.07525 (11) | 0.0788 (11) | |
H8A | −0.1639 | 1.2026 | 0.0947 | 0.118* | |
H8B | −0.3045 | 1.0033 | 0.0967 | 0.118* | |
H8C | −0.3175 | 1.2056 | 0.0547 | 0.118* | |
C9 | −0.2799 (4) | 0.7771 (6) | 0.01449 (10) | 0.0671 (9) | |
H9A | −0.2244 | 0.6659 | −0.0060 | 0.101* | |
H9B | −0.3538 | 0.8836 | −0.0060 | 0.101* | |
H9C | −0.3416 | 0.6807 | 0.0360 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0556 (19) | 0.0747 (15) | 0.0506 (10) | −0.0181 (13) | −0.0028 (11) | 0.0188 (11) |
N1 | 0.059 (2) | 0.0433 (15) | 0.0454 (11) | −0.0073 (15) | 0.0001 (12) | 0.0025 (12) |
S1 | 0.0583 (7) | 0.0424 (4) | 0.0406 (3) | −0.0100 (4) | 0.0064 (3) | 0.0056 (3) |
O2 | 0.0989 (18) | 0.0426 (11) | 0.0526 (10) | −0.0136 (12) | 0.0019 (11) | 0.0128 (9) |
O3 | 0.0452 (16) | 0.0920 (16) | 0.0661 (12) | 0.0021 (14) | 0.0210 (10) | −0.0018 (12) |
C1 | 0.0358 (19) | 0.0342 (13) | 0.0414 (11) | −0.0036 (14) | 0.0021 (12) | 0.0037 (12) |
C2 | 0.051 (2) | 0.0407 (15) | 0.0574 (15) | 0.0045 (16) | 0.0051 (14) | 0.0071 (13) |
C3 | 0.072 (3) | 0.0555 (18) | 0.0612 (16) | 0.0039 (19) | 0.0208 (16) | −0.0105 (16) |
C4 | 0.068 (3) | 0.076 (2) | 0.0432 (13) | −0.008 (2) | 0.0095 (15) | −0.0007 (16) |
C5 | 0.058 (2) | 0.065 (2) | 0.0489 (14) | 0.0040 (19) | −0.0014 (14) | 0.0213 (15) |
C6 | 0.046 (2) | 0.0488 (16) | 0.0553 (14) | 0.0053 (16) | 0.0076 (13) | 0.0035 (13) |
N2 | 0.0432 (17) | 0.0563 (14) | 0.0439 (11) | −0.0032 (13) | 0.0100 (11) | 0.0031 (11) |
C7 | 0.054 (2) | 0.0496 (16) | 0.0397 (12) | −0.0027 (15) | 0.0075 (12) | 0.0030 (11) |
C8 | 0.089 (3) | 0.080 (2) | 0.0748 (18) | −0.011 (2) | 0.0413 (19) | −0.0147 (18) |
C9 | 0.057 (2) | 0.073 (2) | 0.0708 (17) | −0.0115 (19) | 0.0040 (16) | 0.0031 (17) |
Geometric parameters (Å, º) top
O1—N1 | 1.404 (3) | C5—C6 | 1.389 (3) |
O1—H1O | 0.92 (3) | C5—H5A | 0.9300 |
N1—S1 | 1.644 (2) | C6—H6A | 0.9300 |
N1—H1N | 0.82 (3) | N2—C7 | 1.469 (3) |
S1—O2 | 1.4259 (18) | N2—C8 | 1.459 (3) |
S1—O3 | 1.432 (2) | N2—C9 | 1.467 (3) |
S1—C1 | 1.764 (2) | C7—C7i | 1.511 (5) |
C1—C2 | 1.371 (3) | C7—H7A | 0.9700 |
C1—C6 | 1.374 (3) | C7—H7B | 0.9700 |
C2—C3 | 1.376 (3) | C8—H8A | 0.9600 |
C2—H2B | 0.9300 | C8—H8B | 0.9600 |
C3—C4 | 1.363 (4) | C8—H8C | 0.9600 |
C3—H3B | 0.9300 | C9—H9A | 0.9600 |
C4—C5 | 1.364 (4) | C9—H9B | 0.9600 |
C4—H4A | 0.9300 | C9—H9C | 0.9600 |
| | | |
N1—O1—H1O | 107.3 (19) | C1—C6—C5 | 119.1 (3) |
O1—N1—S1 | 112.2 (2) | C1—C6—H6A | 120.4 |
O1—N1—H1N | 113 (2) | C5—C6—H6A | 120.4 |
S1—N1—H1N | 107 (2) | C7—N2—C8 | 109.3 (2) |
O2—S1—O3 | 120.21 (13) | C7—N2—C9 | 111.81 (19) |
O2—S1—N1 | 106.10 (14) | C8—N2—C9 | 109.1 (2) |
O3—S1—N1 | 104.74 (16) | N2—C7—C7i | 112.3 (3) |
O2—S1—C1 | 106.97 (12) | N2—C7—H7A | 109.2 |
O3—S1—C1 | 109.27 (11) | C7i—C7—H7A | 109.2 |
N1—S1—C1 | 109.15 (12) | N2—C7—H7B | 109.2 |
C2—C1—C6 | 120.7 (2) | C7i—C7—H7B | 109.2 |
C2—C1—S1 | 120.32 (19) | H7A—C7—H7B | 107.9 |
C6—C1—S1 | 119.0 (2) | N2—C8—H8A | 109.5 |
C1—C2—C3 | 119.6 (3) | N2—C8—H8B | 109.5 |
C1—C2—H2B | 120.2 | H8A—C8—H8B | 109.5 |
C3—C2—H2B | 120.2 | N2—C8—H8C | 109.5 |
C4—C3—C2 | 119.9 (3) | H8A—C8—H8C | 109.5 |
C4—C3—H3B | 120.1 | H8B—C8—H8C | 109.5 |
C2—C3—H3B | 120.1 | N2—C9—H9A | 109.5 |
C5—C4—C3 | 121.0 (2) | N2—C9—H9B | 109.5 |
C5—C4—H4A | 119.5 | H9A—C9—H9B | 109.5 |
C3—C4—H4A | 119.5 | N2—C9—H9C | 109.5 |
C4—C5—C6 | 119.7 (3) | H9A—C9—H9C | 109.5 |
C4—C5—H5A | 120.2 | H9B—C9—H9C | 109.5 |
C6—C5—H5A | 120.2 | | |
Symmetry code: (i) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2 | 0.92 (3) | 1.76 (3) | 2.678 (3) | 177 (3) |
N1—H1N···O2ii | 0.82 (3) | 2.23 (3) | 3.007 (3) | 159 (3) |
Symmetry code: (ii) x, y−1, z. |
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