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The title compound, C9H12N2O2, is the product of the second step in the synthesis of N-(4-amino-3-methoxy­phenyl)­methanesulfon­amide, the side chain of an anticancer drug (viz. Amsacrine). The compound, obtained by the reduction of N-(2-methoxy-4-nitro­phenyl)­acet­amide in EtOH with Pd/C as catalyst, under a hydrogen atmosphere, crystallizes from ethyl­aceto­acetate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008061/bt6138sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008061/bt6138Isup2.hkl
Contains datablock I

CCDC reference: 189383

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.063
  • wR factor = 0.225
  • Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.33 From the CIF: _reflns_number_total 1693 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1854 Completeness (_total/calc) 91.32% Alert C: < 95% complete PLAT_353 Alert C Long N-H Bond (0.87A) N(11) - H(11A) = 1.03 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: KappaCCD Software (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

(I) top
Crystal data top
C9H12N2O2Dx = 1.313 Mg m3
Mr = 180.21Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 12674 reflections
a = 13.9100 (2) Åθ = 1–26.3°
b = 7.9890 (6) ŵ = 0.09 mm1
c = 16.4080 (7) ÅT = 293 K
V = 1823.37 (16) Å3Rectangular, red
Z = 80.4 × 0.2 × 0.1 mm
F(000) = 768
Data collection top
KappaCCD
diffractometer
1532 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 26.3°, θmin = 2.5°
φ scanh = 617
12674 measured reflectionsk = 148
1693 independent reflectionsl = 200
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H atoms treated by a mixture of independent and constrained refinement
S = 1.21 w = 1/[σ2(Fo2) + (0.1378P)2 + 0.5336P]
where P = (Fo2 + 2Fc2)/3
1693 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.44 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*/Ueq
O10.34068 (9)0.1971 (2)0.67897 (9)0.0428 (5)
C20.24254 (14)0.2035 (2)0.68092 (12)0.0327 (5)
C30.24900 (16)0.0003 (3)0.88189 (13)0.0404 (5)
C40.18692 (15)0.2786 (3)0.62163 (12)0.0364 (5)
H40.21850.33380.56880.044*
N50.26459 (12)0.0538 (2)0.80565 (11)0.0410 (5)
H50.32860.04170.78880.049*
C60.20003 (13)0.1276 (2)0.74932 (10)0.0340 (5)
C70.08642 (15)0.2802 (3)0.62891 (12)0.0394 (5)
O80.16970 (13)0.0003 (3)0.91480 (11)0.0644 (6)
C90.10118 (14)0.1311 (3)0.75663 (12)0.0421 (6)
H90.06890.08210.80500.051*
C100.04441 (14)0.2084 (3)0.69760 (14)0.0442 (6)
H100.03110.21260.70310.053*
N110.03131 (14)0.3487 (3)0.56687 (13)0.0612 (7)
H11A0.03970.37050.58190.073*
H11B0.06460.38800.51650.073*
C120.38779 (16)0.2705 (3)0.61126 (15)0.0499 (6)
H12A0.45310.25550.61680.060*
H12B0.37560.21300.56040.060*
H12C0.38550.38620.60930.060*
C130.33733 (18)0.0593 (4)0.92537 (15)0.0545 (7)
H13A0.32050.09640.97920.065*
H13B0.38240.03140.92910.065*
H13C0.36590.15020.89580.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0299 (8)0.0586 (11)0.0398 (9)0.0004 (6)0.0010 (5)0.0111 (6)
C20.0327 (10)0.0338 (11)0.0315 (10)0.0011 (6)0.0005 (7)0.0021 (7)
C30.0499 (12)0.0384 (12)0.0328 (10)0.0035 (8)0.0020 (8)0.0011 (8)
C40.0373 (11)0.0392 (12)0.0326 (10)0.0018 (7)0.0001 (7)0.0002 (7)
N50.0386 (9)0.0511 (11)0.0333 (9)0.0035 (7)0.0018 (6)0.0074 (7)
C60.0359 (10)0.0357 (12)0.0303 (10)0.0000 (7)0.0005 (7)0.0002 (7)
C70.0387 (11)0.0426 (12)0.0370 (11)0.0059 (8)0.0057 (8)0.0032 (7)
O80.0557 (11)0.0954 (16)0.0421 (10)0.0068 (9)0.0096 (7)0.0141 (9)
C90.0392 (11)0.0483 (14)0.0389 (11)0.0030 (8)0.0073 (8)0.0004 (8)
C100.0327 (10)0.0539 (14)0.0461 (12)0.0018 (8)0.0007 (8)0.0010 (9)
N110.0438 (11)0.0869 (17)0.0528 (12)0.0180 (10)0.0068 (9)0.0140 (11)
C120.0403 (11)0.0635 (15)0.0459 (13)0.0030 (9)0.0091 (9)0.0104 (10)
C130.0636 (16)0.0626 (17)0.0374 (12)0.0050 (11)0.0042 (9)0.0086 (10)
Geometric parameters (Å, º) top
O1—C21.366 (2)C7—C101.393 (3)
O1—C121.417 (3)C9—C101.394 (3)
C2—C41.380 (3)C9—H90.9925
C2—C61.406 (3)C10—H101.0552
C3—O81.228 (3)N11—H11A1.0334
C3—N51.341 (3)N11—H11B0.9980
C3—C131.497 (3)C12—H12A0.9211
C4—C71.403 (3)C12—H12B0.9676
C4—H41.0666C12—H12C0.9253
N5—C61.417 (2)C13—H13A0.9600
N5—H50.9377C13—H13B0.9601
C6—C91.381 (3)C13—H13C0.9600
C7—N111.387 (3)
C2—O1—C12117.73 (16)C6—C9—H9120.8
O1—C2—C4124.02 (18)C10—C9—H9118.3
O1—C2—C6115.01 (17)C7—C10—C9120.47 (18)
C4—C2—C6120.96 (18)C7—C10—H10118.3
O8—C3—N5123.7 (2)C9—C10—H10121.2
O8—C3—C13121.9 (2)C7—N11—H11A114.8
N5—C3—C13114.41 (19)C7—N11—H11B118.4
C2—C4—C7120.16 (18)H11A—N11—H11B126.0
C2—C4—H4121.4O1—C12—H12A109.0
C7—C4—H4118.4O1—C12—H12B113.5
C3—N5—C6129.78 (17)H12A—C12—H12B101.3
C3—N5—H5113.3O1—C12—H12C115.1
C6—N5—H5116.9H12A—C12—H12C99.6
C9—C6—C2118.65 (17)H12B—C12—H12C116.0
C9—C6—N5125.66 (17)C3—C13—H13A109.6
C2—C6—N5115.69 (16)C3—C13—H13B109.1
N11—C7—C10121.63 (19)H13A—C13—H13B109.5
N11—C7—C4119.47 (19)C3—C13—H13C109.7
C10—C7—C4118.88 (18)H13A—C13—H13C109.5
C6—C9—C10120.85 (18)H13B—C13—H13C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O10.942.192.598 (2)105
N11—H11A···O8i1.032.093.062 (3)157
N11—H11B···O8ii1.002.393.374 (3)168
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x, y+1/2, z1/2.
 

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