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In the crystal structure of the title compound, the sulfonamide N—H group forms an inter­molecular hydrogen bond to the amine N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901502191X/gk2646sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901502191X/gk2646Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901502191X/gk2646Isup3.cml
Supplementary material

CCDC reference: 1437453

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B .. Please Check
Alert level G PLAT791_ALERT_4_G The Model has Chirality at C1 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C2 (Chiral SPGR) S Verify PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and su .. 0.02 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

N-[(1S,2S)-2-Aminocyclohexyl]-2,4,6-trimethylbenzenesulfonamide top
Crystal data top
C15H24N2O2SDx = 1.289 Mg m3
Mr = 296.42Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9968 reflections
a = 6.5215 (4) Åθ = 2.2–25.3°
b = 10.0202 (6) ŵ = 0.22 mm1
c = 23.3660 (15) ÅT = 173 K
V = 1526.89 (16) Å3Block, colourless
Z = 40.37 × 0.20 × 0.15 mm
F(000) = 640
Data collection top
Bruker APEXII CCD
diffractometer
2799 independent reflections
Radiation source: sealed tube2667 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8 pixels mm-1θmax = 25.4°, θmin = 1.7°
φ and ω scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1212
Tmin = 0.706, Tmax = 0.745l = 2828
25587 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0313P)2 + 0.5049P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.19 e Å3
2799 reflectionsΔρmin = 0.21 e Å3
196 parametersAbsolute structure: Flack parameter x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.00 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.39425 (9)0.81200 (6)0.62892 (2)0.03018 (16)
O10.2464 (3)0.72704 (19)0.65596 (8)0.0412 (4)
O20.3238 (3)0.93797 (17)0.60697 (8)0.0408 (5)
N10.5015 (3)0.7361 (2)0.57616 (9)0.0297 (5)
N20.9140 (3)0.6769 (2)0.54061 (8)0.0287 (4)
C10.5776 (3)0.5984 (2)0.58084 (9)0.0238 (5)
H1A0.64250.58720.61930.029*
C20.7442 (3)0.5816 (2)0.53502 (9)0.0234 (5)
H20.67800.59860.49710.028*
C30.8271 (3)0.4398 (2)0.53360 (10)0.0273 (5)
H3A0.90520.42250.56920.033*
H3B0.92280.43060.50090.033*
C40.6574 (4)0.3363 (2)0.52793 (10)0.0308 (5)
H4A0.71740.24570.53000.037*
H4B0.59020.34600.49020.037*
C50.4980 (4)0.3528 (2)0.57518 (11)0.0314 (5)
H5A0.38640.28710.56960.038*
H5B0.56240.33530.61280.038*
C60.4094 (4)0.4934 (2)0.57442 (10)0.0300 (5)
H6A0.30950.50310.60610.036*
H6B0.33560.50800.53790.036*
C70.5988 (4)0.8413 (2)0.67770 (9)0.0252 (5)
C80.7523 (4)0.9336 (2)0.66163 (9)0.0270 (5)
C90.9071 (4)0.9619 (2)0.69984 (10)0.0321 (5)
H91.01191.02250.68870.039*
C100.9154 (4)0.9054 (2)0.75383 (10)0.0340 (6)
C110.7662 (4)0.8131 (3)0.76822 (10)0.0346 (5)
H110.77240.77230.80490.042*
C120.6078 (4)0.7775 (2)0.73148 (9)0.0291 (5)
C130.7568 (5)1.0087 (2)0.60541 (10)0.0384 (6)
H13A0.70840.95020.57460.058*
H13B0.89741.03730.59720.058*
H13C0.66751.08710.60800.058*
C141.0799 (5)0.9459 (3)0.79566 (13)0.0532 (8)
H14A1.21170.95230.77570.080*
H14B1.08970.87890.82610.080*
H14C1.04521.03270.81240.080*
C150.4607 (5)0.6726 (3)0.75300 (12)0.0440 (7)
H15A0.32360.71160.75690.066*
H15B0.50710.63990.79030.066*
H15C0.45590.59830.72580.066*
H2A0.864 (5)0.754 (3)0.5537 (12)0.047 (8)*
H10.484 (5)0.768 (3)0.5458 (13)0.040 (8)*
H2B1.003 (5)0.645 (3)0.5683 (13)0.045 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0271 (3)0.0327 (3)0.0307 (3)0.0072 (3)0.0005 (3)0.0065 (2)
O10.0275 (8)0.0496 (11)0.0465 (10)0.0037 (8)0.0092 (8)0.0111 (8)
O20.0427 (10)0.0387 (10)0.0410 (10)0.0196 (8)0.0057 (8)0.0067 (8)
N10.0371 (11)0.0293 (11)0.0228 (10)0.0109 (9)0.0014 (9)0.0010 (9)
N20.0283 (10)0.0250 (10)0.0329 (10)0.0021 (9)0.0002 (9)0.0004 (9)
C10.0239 (11)0.0250 (11)0.0225 (10)0.0044 (9)0.0012 (9)0.0009 (9)
C20.0228 (10)0.0238 (11)0.0236 (10)0.0009 (9)0.0001 (9)0.0016 (9)
C30.0261 (11)0.0259 (12)0.0300 (12)0.0053 (10)0.0036 (9)0.0003 (9)
C40.0357 (13)0.0241 (11)0.0326 (12)0.0008 (10)0.0001 (10)0.0010 (9)
C50.0315 (13)0.0313 (13)0.0315 (12)0.0059 (10)0.0014 (10)0.0010 (10)
C60.0229 (11)0.0359 (12)0.0312 (11)0.0006 (11)0.0032 (11)0.0033 (10)
C70.0278 (11)0.0242 (10)0.0235 (10)0.0038 (10)0.0040 (10)0.0040 (8)
C80.0327 (12)0.0217 (11)0.0267 (11)0.0030 (10)0.0081 (10)0.0020 (9)
C90.0291 (12)0.0290 (12)0.0382 (13)0.0015 (11)0.0069 (12)0.0045 (10)
C100.0319 (13)0.0361 (13)0.0340 (13)0.0076 (11)0.0008 (11)0.0102 (10)
C110.0465 (14)0.0342 (12)0.0232 (11)0.0075 (13)0.0014 (11)0.0010 (10)
C120.0367 (12)0.0247 (11)0.0259 (11)0.0018 (11)0.0062 (11)0.0010 (9)
C130.0536 (16)0.0285 (12)0.0331 (13)0.0021 (12)0.0098 (13)0.0058 (11)
C140.0455 (18)0.0629 (19)0.0512 (17)0.0037 (16)0.0124 (16)0.0140 (15)
C150.0569 (18)0.0351 (14)0.0401 (14)0.0079 (13)0.0094 (13)0.0066 (12)
Geometric parameters (Å, º) top
S1—O11.4330 (19)C6—H6A0.9900
S1—O21.4379 (18)C6—H6B0.9900
S1—N11.609 (2)C7—C81.414 (3)
S1—C71.779 (2)C7—C121.411 (3)
N1—C11.470 (3)C8—C91.377 (3)
N1—H10.79 (3)C8—C131.514 (3)
N2—C21.469 (3)C9—H90.9500
N2—H2A0.89 (3)C9—C101.384 (3)
N2—H2B0.93 (3)C10—C111.384 (4)
C1—H1A1.0000C10—C141.507 (4)
C1—C21.535 (3)C11—H110.9500
C1—C61.527 (3)C11—C121.390 (4)
C2—H21.0000C12—C151.509 (3)
C2—C31.521 (3)C13—H13A0.9800
C3—H3A0.9900C13—H13B0.9800
C3—H3B0.9900C13—H13C0.9800
C3—C41.522 (3)C14—H14A0.9800
C4—H4A0.9900C14—H14B0.9800
C4—H4B0.9900C14—H14C0.9800
C4—C51.525 (3)C15—H15A0.9800
C5—H5A0.9900C15—H15B0.9800
C5—H5B0.9900C15—H15C0.9800
C5—C61.523 (3)
O1—S1—O2117.62 (12)C1—C6—H6A109.4
O1—S1—N1110.46 (11)C1—C6—H6B109.4
O1—S1—C7108.68 (11)C5—C6—C1111.33 (19)
O2—S1—N1106.31 (11)C5—C6—H6A109.4
O2—S1—C7108.86 (11)C5—C6—H6B109.4
N1—S1—C7104.06 (11)H6A—C6—H6B108.0
S1—N1—H1116 (2)C8—C7—S1117.96 (16)
C1—N1—S1122.24 (17)C12—C7—S1121.78 (19)
C1—N1—H1120 (2)C12—C7—C8120.2 (2)
C2—N2—H2A108 (2)C7—C8—C13124.7 (2)
C2—N2—H2B108.1 (18)C9—C8—C7118.8 (2)
H2A—N2—H2B107 (3)C9—C8—C13116.5 (2)
N1—C1—H1A108.4C8—C9—H9118.8
N1—C1—C2106.87 (18)C8—C9—C10122.4 (2)
N1—C1—C6113.39 (19)C10—C9—H9118.8
C2—C1—H1A108.4C9—C10—C14120.6 (3)
C6—C1—H1A108.4C11—C10—C9117.9 (2)
C6—C1—C2111.36 (17)C11—C10—C14121.5 (2)
N2—C2—C1113.59 (18)C10—C11—H11118.5
N2—C2—H2107.1C10—C11—C12123.0 (2)
N2—C2—C3109.98 (18)C12—C11—H11118.5
C1—C2—H2107.1C7—C12—C15125.9 (2)
C3—C2—C1111.70 (18)C11—C12—C7117.7 (2)
C3—C2—H2107.1C11—C12—C15116.5 (2)
C2—C3—H3A109.1C8—C13—H13A109.5
C2—C3—H3B109.1C8—C13—H13B109.5
C2—C3—C4112.32 (19)C8—C13—H13C109.5
H3A—C3—H3B107.9H13A—C13—H13B109.5
C4—C3—H3A109.1H13A—C13—H13C109.5
C4—C3—H3B109.1H13B—C13—H13C109.5
C3—C4—H4A109.4C10—C14—H14A109.5
C3—C4—H4B109.4C10—C14—H14B109.5
C3—C4—C5111.02 (19)C10—C14—H14C109.5
H4A—C4—H4B108.0H14A—C14—H14B109.5
C5—C4—H4A109.4H14A—C14—H14C109.5
C5—C4—H4B109.4H14B—C14—H14C109.5
C4—C5—H5A109.5C12—C15—H15A109.5
C4—C5—H5B109.5C12—C15—H15B109.5
H5A—C5—H5B108.1C12—C15—H15C109.5
C6—C5—C4110.51 (19)H15A—C15—H15B109.5
C6—C5—H5A109.5H15A—C15—H15C109.5
C6—C5—H5B109.5H15B—C15—H15C109.5
S1—N1—C1—C2156.04 (17)C2—C1—C6—C555.2 (2)
S1—N1—C1—C680.9 (2)C2—C3—C4—C555.0 (3)
S1—C7—C8—C9177.22 (17)C3—C4—C5—C656.8 (3)
S1—C7—C8—C130.7 (3)C4—C5—C6—C157.3 (3)
S1—C7—C12—C11175.90 (18)C6—C1—C2—N2177.74 (19)
S1—C7—C12—C154.4 (3)C6—C1—C2—C352.6 (2)
O1—S1—N1—C146.1 (2)C7—S1—N1—C170.4 (2)
O1—S1—C7—C8173.93 (17)C7—C8—C9—C101.4 (3)
O1—S1—C7—C124.7 (2)C8—C7—C12—C112.7 (3)
O2—S1—N1—C1174.73 (18)C8—C7—C12—C15177.0 (2)
O2—S1—C7—C844.7 (2)C8—C9—C10—C112.8 (4)
O2—S1—C7—C12133.97 (19)C8—C9—C10—C14176.1 (2)
N1—S1—C7—C868.36 (19)C9—C10—C11—C121.4 (4)
N1—S1—C7—C12112.99 (19)C10—C11—C12—C71.3 (4)
N1—C1—C2—N257.9 (2)C10—C11—C12—C15178.4 (2)
N1—C1—C2—C3176.97 (18)C12—C7—C8—C91.5 (3)
N1—C1—C6—C5175.8 (2)C12—C7—C8—C13179.4 (2)
N2—C2—C3—C4179.90 (18)C13—C8—C9—C10176.7 (2)
C1—C2—C3—C452.8 (3)C14—C10—C11—C12177.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.89 (3)2.43 (3)2.877 (3)111 (2)
N1—H1···N2i0.79 (3)2.14 (3)2.921 (3)170 (3)
Symmetry code: (i) x1/2, y+3/2, z+1.
 

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