Literature DB >> 21201389

N-(2-Chloro-2-nitro-1-phenyl-prop-yl)-4-methyl-benzene-sulfonamide.

Sanjun Zhi1, Tengfei Li, Guanghui An, Yi Pan.   

Abstract

In the title compound, C(16)H(17)ClN(2)O(4)S, the dihedral angle between the phenyl and benzene rings is 19.4 (2)°. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds, as well as by intra- and inter-molecular C-H⋯O hydrogen bonds.

Entities:  

Year:  2008        PMID： 21201389      PMCID： PMC2960443          DOI： 10.1107/S1600536807067712

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see Kemp (1991 ▶); Qui & Silverman (2000 ▶); Orlek & Stemp (1991 ▶), Han et al. (2007 ▶); Li et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H17ClN2O4S M = 368.83 Orthorhombic, a = 7.8254 (8) Å b = 19.610 (2) Å c = 22.533 (3) Å V = 3457.8 (7) Å3 Z = 8 Mo Kα radiation μ = 0.36 mm−1 T = 291 (2) K 0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.901, T max = 0.921 17527 measured reflections 3396 independent reflections 2467 reflections with I > 2σ(I) R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.125 S = 1.01 3396 reflections 222 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.28 e Å−3 Δρmin = −0.26 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067712/at2518sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067712/at2518Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H17ClN2O4SDx = 1.417 Mg m−3
Mr = 368.83Melting point: 423.2 K
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7468 reflections
a = 7.8254 (8) Åθ = 2.3–27.9º
b = 19.610 (2) ŵ = 0.36 mm−1
c = 22.533 (3) ÅT = 291 (2) K
V = 3457.8 (7) Å3Block, colourless
Z = 80.30 × 0.26 × 0.24 mm
F000 = 1536
Bruker SMART APEX CCD area-detector diffractometer3396 independent reflections
Radiation source: sealed tube2467 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.070
T = 291(2) Kθmax = 26.0º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −9→8
Tmin = 0.901, Tmax = 0.921k = −24→24
17527 measured reflectionsl = −16→27
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.06P)2 + 0.58P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3396 reflectionsΔρmax = 0.28 e Å−3
222 parametersΔρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
C10.7916 (4)0.10320 (17)0.61740 (13)0.0374 (7)
H1A0.77090.10300.65940.056*
H1B0.86060.14200.60720.056*
H1C0.85030.06210.60640.056*
C20.6185 (4)0.10723 (16)0.58376 (13)0.0333 (7)
C30.5059 (4)0.16923 (14)0.59888 (13)0.0292 (6)
H30.39950.16450.57630.035*
C40.5853 (3)0.23727 (15)0.58138 (13)0.0293 (6)
C50.5405 (4)0.26704 (17)0.52790 (13)0.0362 (7)
H50.46510.24450.50280.043*
C60.6055 (4)0.32954 (17)0.51103 (14)0.0415 (8)
H60.57650.34840.47450.050*
C70.7156 (4)0.36407 (18)0.54968 (15)0.0437 (8)
H70.75700.40700.53960.052*
C80.7623 (4)0.33466 (18)0.60226 (15)0.0444 (8)
H80.83810.35720.62730.053*
C90.6972 (4)0.27113 (17)0.61859 (14)0.0414 (8)
H90.72900.25160.65450.050*
C100.3185 (3)0.28495 (15)0.69070 (12)0.0314 (6)
C110.2653 (4)0.32776 (18)0.64579 (14)0.0402 (7)
H110.20850.30990.61310.048*
C120.2959 (5)0.39679 (18)0.64904 (15)0.0465 (8)
H120.26010.42520.61840.056*
C130.3804 (4)0.42454 (18)0.69822 (14)0.0419 (8)
C140.4350 (4)0.38054 (17)0.74268 (15)0.0423 (8)
H140.49390.39800.77510.051*
C150.4037 (4)0.31171 (16)0.73966 (13)0.0349 (7)
H150.43920.28310.77020.042*
C160.4064 (4)0.49975 (18)0.70326 (17)0.0491 (9)
H16A0.32410.51840.73040.074*
H16B0.39220.52040.66500.074*
H16C0.51960.50870.71770.074*
Cl10.65350 (9)0.10276 (4)0.50665 (3)0.03580 (19)
N10.5083 (4)0.04372 (13)0.59707 (12)0.0407 (6)
N20.4620 (3)0.16217 (13)0.66251 (11)0.0334 (6)
H2A0.547 (4)0.1794 (17)0.6841 (15)0.040*
O10.1557 (3)0.18367 (12)0.64347 (10)0.0439 (6)
O20.2635 (3)0.17162 (12)0.74582 (9)0.0432 (6)
O30.3667 (3)0.04155 (12)0.57591 (12)0.0547 (7)
O40.5674 (3)−0.00057 (13)0.62846 (12)0.0595 (7)
S10.28433 (9)0.19677 (4)0.68662 (3)0.03081 (19)
U11U22U33U12U13U23
C10.0406 (16)0.0483 (18)0.0233 (14)0.0236 (14)−0.0020 (12)−0.0033 (14)
C20.0365 (16)0.0373 (16)0.0261 (14)0.0020 (13)0.0056 (12)−0.0015 (13)
C30.0296 (15)0.0309 (14)0.0270 (14)−0.0002 (12)0.0055 (11)−0.0002 (12)
C40.0267 (14)0.0322 (15)0.0290 (15)−0.0027 (11)0.0033 (12)−0.0024 (12)
C50.0344 (15)0.0448 (17)0.0295 (15)−0.0005 (14)−0.0042 (12)0.0001 (13)
C60.056 (2)0.0446 (19)0.0242 (16)0.0022 (15)0.0026 (14)0.0134 (14)
C70.0534 (19)0.0383 (18)0.0393 (19)−0.0083 (15)0.0079 (15)0.0100 (15)
C80.0513 (19)0.0471 (19)0.0349 (18)−0.0214 (16)0.0037 (15)0.0031 (15)
C90.0496 (18)0.0467 (19)0.0279 (15)−0.0154 (15)−0.0060 (14)0.0084 (14)
C100.0265 (14)0.0402 (17)0.0275 (15)0.0008 (12)0.0057 (11)0.0011 (12)
C110.0452 (17)0.0461 (19)0.0293 (16)0.0124 (14)−0.0042 (14)0.0062 (14)
C120.059 (2)0.0433 (19)0.0368 (18)0.0120 (16)−0.0016 (16)0.0137 (16)
C130.0474 (19)0.0432 (18)0.0350 (17)−0.0008 (14)0.0099 (14)0.0068 (15)
C140.0435 (18)0.0471 (19)0.0363 (17)−0.0077 (14)−0.0042 (14)−0.0025 (15)
C150.0373 (15)0.0392 (16)0.0281 (15)−0.0009 (13)−0.0026 (12)0.0021 (13)
C160.0394 (17)0.050 (2)0.058 (2)−0.0181 (15)0.0056 (17)0.0087 (18)
Cl10.0403 (4)0.0396 (4)0.0275 (4)0.0017 (3)0.0128 (3)−0.0108 (3)
N10.0507 (17)0.0366 (15)0.0347 (15)−0.0014 (13)0.0048 (13)−0.0007 (12)
N20.0326 (13)0.0325 (14)0.0351 (15)0.0000 (10)0.0028 (11)−0.0005 (11)
O10.0323 (10)0.0607 (15)0.0387 (12)−0.0070 (10)−0.0006 (10)−0.0059 (11)
O20.0565 (14)0.0451 (13)0.0281 (11)−0.0041 (10)0.0182 (11)0.0042 (10)
O30.0564 (15)0.0482 (14)0.0597 (17)−0.0259 (12)0.0007 (13)−0.0081 (12)
O40.0644 (16)0.0474 (15)0.0667 (18)0.0107 (12)0.0152 (14)0.0303 (14)
S10.0299 (3)0.0364 (4)0.0261 (4)−0.0028 (3)0.0059 (3)0.0004 (3)
C1—C21.555 (4)C10—C111.379 (4)
C1—H1A0.9600C10—C151.392 (4)
C1—H1B0.9600C10—S11.752 (3)
C1—H1C0.9600C11—C121.377 (5)
C2—C31.539 (4)C11—H110.9300
C2—N11.544 (4)C12—C131.400 (5)
C2—Cl11.761 (3)C12—H120.9300
C3—N21.481 (4)C13—C141.390 (5)
C3—C41.524 (4)C13—C161.493 (5)
C3—H30.9800C14—C151.373 (4)
C4—C91.382 (4)C14—H140.9300
C4—C51.384 (4)C15—H150.9300
C5—C61.380 (4)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.400 (5)C16—H16C0.9600
C6—H60.9300N1—O31.207 (3)
C7—C81.367 (5)N1—O41.212 (3)
C7—H70.9300N2—S11.639 (3)
C8—C91.395 (4)N2—H2A0.89 (3)
C8—H80.9300O1—S11.423 (2)
C9—H90.9300O2—S11.432 (2)
C2—C1—H1A109.5C11—C10—C15119.8 (3)
C2—C1—H1B109.5C11—C10—S1121.1 (2)
H1A—C1—H1B109.5C15—C10—S1119.1 (2)
C2—C1—H1C109.5C12—C11—C10120.5 (3)
H1A—C1—H1C109.5C12—C11—H11119.8
H1B—C1—H1C109.5C10—C11—H11119.8
C3—C2—N1105.9 (2)C11—C12—C13120.4 (3)
C3—C2—C1115.5 (2)C11—C12—H12119.8
N1—C2—C1110.5 (2)C13—C12—H12119.8
C3—C2—Cl1110.3 (2)C14—C13—C12118.3 (3)
N1—C2—Cl1103.78 (19)C14—C13—C16121.1 (3)
C1—C2—Cl1110.1 (2)C12—C13—C16120.6 (3)
N2—C3—C4115.3 (2)C15—C14—C13121.3 (3)
N2—C3—C2105.9 (2)C15—C14—H14119.3
C4—C3—C2113.6 (2)C13—C14—H14119.3
N2—C3—H3107.2C14—C15—C10119.7 (3)
C4—C3—H3107.2C14—C15—H15120.2
C2—C3—H3107.2C10—C15—H15120.2
C9—C4—C5119.1 (3)C13—C16—H16A109.5
C9—C4—C3121.5 (3)C13—C16—H16B109.5
C5—C4—C3119.4 (3)H16A—C16—H16B109.5
C6—C5—C4121.4 (3)C13—C16—H16C109.5
C6—C5—H5119.3H16A—C16—H16C109.5
C4—C5—H5119.3H16B—C16—H16C109.5
C5—C6—C7119.0 (3)O3—N1—O4123.8 (3)
C5—C6—H6120.5O3—N1—C2117.7 (3)
C7—C6—H6120.5O4—N1—C2118.6 (3)
C8—C7—C6120.0 (3)C3—N2—S1118.6 (2)
C8—C7—H7120.0C3—N2—H2A109 (2)
C6—C7—H7120.0S1—N2—H2A107 (2)
C7—C8—C9120.5 (3)O1—S1—O2119.59 (14)
C7—C8—H8119.8O1—S1—N2107.37 (14)
C9—C8—H8119.8O2—S1—N2105.25 (14)
C4—C9—C8120.0 (3)O1—S1—C10108.79 (14)
C4—C9—H9120.0O2—S1—C10107.97 (14)
C8—C9—H9120.0N2—S1—C10107.24 (13)
N1—C2—C3—N259.6 (3)C12—C13—C14—C15−1.7 (5)
C1—C2—C3—N2−63.2 (3)C16—C13—C14—C15176.7 (3)
Cl1—C2—C3—N2171.28 (19)C13—C14—C15—C101.2 (5)
N1—C2—C3—C4−172.9 (2)C11—C10—C15—C14−0.4 (4)
C1—C2—C3—C464.4 (3)S1—C10—C15—C14178.4 (2)
Cl1—C2—C3—C4−61.2 (3)C3—C2—N1—O350.9 (3)
N2—C3—C4—C936.7 (4)C1—C2—N1—O3176.7 (3)
C2—C3—C4—C9−85.7 (3)Cl1—C2—N1—O3−65.3 (3)
N2—C3—C4—C5−141.2 (3)C3—C2—N1—O4−128.4 (3)
C2—C3—C4—C596.3 (3)C1—C2—N1—O4−2.5 (4)
C9—C4—C5—C60.2 (5)Cl1—C2—N1—O4115.5 (3)
C3—C4—C5—C6178.1 (3)C4—C3—N2—S180.2 (3)
C4—C5—C6—C7−1.6 (5)C2—C3—N2—S1−153.3 (2)
C5—C6—C7—C82.4 (5)C3—N2—S1—O141.9 (3)
C6—C7—C8—C9−1.8 (5)C3—N2—S1—O2170.3 (2)
C5—C4—C9—C80.5 (5)C3—N2—S1—C10−74.9 (2)
C3—C4—C9—C8−177.4 (3)C11—C10—S1—O1−18.0 (3)
C7—C8—C9—C40.4 (5)C15—C10—S1—O1163.2 (2)
C15—C10—C11—C120.0 (5)C11—C10—S1—O2−149.2 (2)
S1—C10—C11—C12−178.8 (3)C15—C10—S1—O232.0 (3)
C10—C11—C12—C13−0.4 (5)C11—C10—S1—N297.8 (3)
C11—C12—C13—C141.2 (5)C15—C10—S1—N2−80.9 (2)
C11—C12—C13—C16−177.1 (3)
D—H···AD—HH···AD···AD—H···A
C3—H3···O10.982.462.933 (4)109
C3—H3···O30.982.422.779 (4)101
C1—H1A···O2i0.962.523.369 (4)147
C1—H1B···O1ii0.962.583.310 (4)133
N2—H2A···O2i0.89 (2)2.32 (3)3.141 (3)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯O10.982.462.933 (4)109
C3—H3⋯O30.982.422.779 (4)101
C1—H1A⋯O2i0.962.523.369 (4)147
C1—H1B⋯O1ii0.962.583.310 (4)133
N2—H2A⋯O2i0.89 (2)2.32 (3)3.141 (3)153

Symmetry codes: (i) ; (ii) .

  1 in total

1.  A new class of conformationally rigid analogues of 4-amino-5-halopentanoic acids, potent inactivators of gamma-aminobutyric acid aminotransferase.

Authors:  J Qiu; R B Silverman
Journal:  J Med Chem       Date:  2000-02-24       Impact factor: 7.446
  1 in total

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