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The crystal structure of racemic dimethyl (4RS,5RS)-3-(4-nitrophenyl)-4,5-dihydroisoxazole-4,5-dicarboxylate, C13H12N2O7, has been determined by single-crystal X-ray diffraction. By analysing the degree of growth of the morphologically important crystal faces, a ranking of the most relevant non-covalent interactions determining the crystal structure can be inferred. The morphological information is considered with an approach opposite to the conventional one: instead of searching inside the structure for the potential key interactions and using them to calculate the crystal habit, the observed crystal morphology is used to define the preferential lines of growth of the crystal, and then this information is interpreted by means of density functional theory (DFT) calculations. Comparison with the X-ray structure confirms the validity of the strategy, thus suggesting this top–down approach to be a useful tool for crystal engineering.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613030862/bi5027sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613030862/bi5027Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613030862/bi5027sup3.pdf
Details of the morphology prediction

CCDC reference: 958815

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
Dimethyl (4RS,5RS)-3-(4-nitrophenyl)-4,5-dihydroisoxazole-4,5-dicarboxylate top
Crystal data top
C13H12N2O7F(000) = 640
Mr = 308.25Dx = 1.494 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 7.2032 (2) ÅCell parameters from 4957 reflections
b = 6.9183 (3) Åθ = 3.2–69.8°
c = 27.515 (2) ŵ = 1.07 mm1
β = 92.134 (4)°T = 293 K
V = 1370.23 (12) Å3Prism, colorless
Z = 40.90 × 0.45 × 0.25 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2596 independent reflections
Radiation source: fine-focus sealed tube2490 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 69.8°, θmin = 3.2°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 88
Tmin = 0.98, Tmax = 0.99k = 81
4957 measured reflectionsl = 3233
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.4588P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.30 e Å3
2596 reflectionsΔρmin = 0.24 e Å3
248 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0090 (7)
Crystal data top
C13H12N2O7V = 1370.23 (12) Å3
Mr = 308.25Z = 4
Monoclinic, P21/cCu Kα radiation
a = 7.2032 (2) ŵ = 1.07 mm1
b = 6.9183 (3) ÅT = 293 K
c = 27.515 (2) Å0.90 × 0.45 × 0.25 mm
β = 92.134 (4)°
Data collection top
Bruker APEX-II CCD
diffractometer
2596 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
2490 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 0.99Rint = 0.016
4957 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0403 restraints
wR(F2) = 0.114All H-atom parameters refined
S = 1.05Δρmax = 0.30 e Å3
2596 reflectionsΔρmin = 0.24 e Å3
248 parameters
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
N10.1514 (2)0.1930 (2)0.06205 (5)0.0538 (4)
N20.40842 (18)0.84188 (19)0.09400 (5)0.0430 (3)
O10.1488 (3)0.0178 (2)0.05648 (6)0.0821 (5)
O20.1104 (2)0.2730 (2)0.10048 (5)0.0743 (4)
O30.43675 (16)0.93415 (17)0.13944 (4)0.0495 (3)
O40.59575 (17)0.42401 (19)0.14255 (4)0.0543 (3)
O50.5048 (2)0.4656 (3)0.21773 (5)0.0876 (6)
O60.11028 (19)1.07368 (18)0.17241 (5)0.0600 (4)
O70.05328 (16)0.79192 (17)0.20942 (4)0.0510 (3)
C10.2054 (2)0.3150 (2)0.02012 (5)0.0417 (4)
C20.2380 (2)0.5091 (2)0.02755 (5)0.0439 (4)
C30.2866 (2)0.6236 (2)0.01190 (5)0.0403 (3)
C40.29951 (19)0.5448 (2)0.05864 (5)0.0349 (3)
C50.2636 (2)0.3482 (2)0.06492 (6)0.0432 (4)
C60.2183 (2)0.2323 (2)0.02550 (6)0.0470 (4)
C70.34806 (18)0.6699 (2)0.10043 (5)0.0347 (3)
C80.3312 (2)0.6186 (2)0.15339 (5)0.0355 (3)
C90.3426 (2)0.8226 (2)0.17495 (5)0.0403 (4)
C100.4867 (2)0.4927 (2)0.17506 (5)0.0409 (4)
C110.1549 (2)0.9142 (2)0.18422 (5)0.0412 (4)
C120.7500 (3)0.3034 (4)0.15973 (8)0.0684 (6)
C130.1297 (3)0.8578 (3)0.22185 (8)0.0596 (5)
H80.220 (3)0.553 (2)0.1599 (6)0.039 (4)*
H50.268 (3)0.293 (3)0.0972 (7)0.055 (5)*
H20.230 (3)0.561 (3)0.0582 (8)0.055 (5)*
H60.192 (3)0.099 (3)0.0300 (7)0.055 (5)*
H30.314 (3)0.758 (3)0.0075 (7)0.052 (5)*
H1210.791 (5)0.229 (5)0.1359 (10)0.121 (11)*
H1220.704 (4)0.222 (4)0.1839 (11)0.104 (10)*
H1330.180 (3)0.757 (4)0.2416 (10)0.081 (7)*
H1310.201 (3)0.881 (4)0.1921 (10)0.075 (7)*
H1320.126 (4)0.983 (4)0.2392 (10)0.088 (8)*
H1230.836 (4)0.381 (4)0.1734 (11)0.106 (11)*
H90.414 (3)0.827 (3)0.2054 (7)0.051 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0537 (8)0.0654 (10)0.0423 (8)0.0091 (7)0.0009 (6)0.0122 (7)
N20.0487 (7)0.0416 (7)0.0386 (7)0.0011 (5)0.0016 (5)0.0008 (5)
O10.1212 (14)0.0595 (9)0.0653 (9)0.0237 (9)0.0023 (9)0.0174 (7)
O20.0896 (10)0.0886 (11)0.0433 (7)0.0087 (8)0.0142 (6)0.0109 (7)
O30.0560 (7)0.0461 (6)0.0467 (6)0.0109 (5)0.0037 (5)0.0090 (5)
O40.0573 (7)0.0662 (8)0.0391 (6)0.0304 (6)0.0012 (5)0.0069 (5)
O50.1002 (12)0.1259 (14)0.0368 (7)0.0538 (11)0.0029 (7)0.0226 (8)
O60.0652 (8)0.0451 (7)0.0698 (8)0.0140 (6)0.0044 (6)0.0049 (6)
O70.0523 (6)0.0531 (7)0.0482 (6)0.0166 (5)0.0102 (5)0.0071 (5)
C10.0382 (7)0.0502 (9)0.0367 (8)0.0000 (6)0.0006 (6)0.0078 (6)
C20.0487 (8)0.0529 (9)0.0300 (7)0.0051 (7)0.0006 (6)0.0033 (6)
C30.0483 (8)0.0373 (8)0.0353 (7)0.0053 (6)0.0001 (6)0.0037 (6)
C40.0346 (6)0.0384 (7)0.0315 (7)0.0064 (5)0.0006 (5)0.0020 (5)
C50.0532 (9)0.0413 (8)0.0347 (7)0.0001 (7)0.0032 (6)0.0050 (6)
C60.0552 (9)0.0397 (8)0.0458 (9)0.0042 (7)0.0014 (7)0.0001 (7)
C70.0346 (6)0.0359 (7)0.0333 (7)0.0064 (5)0.0008 (5)0.0028 (5)
C80.0375 (7)0.0390 (7)0.0301 (7)0.0038 (6)0.0001 (5)0.0008 (5)
C90.0440 (8)0.0432 (8)0.0332 (7)0.0026 (6)0.0042 (6)0.0046 (6)
C100.0470 (8)0.0420 (8)0.0336 (7)0.0049 (6)0.0021 (6)0.0053 (6)
C110.0498 (8)0.0418 (8)0.0317 (7)0.0066 (6)0.0035 (6)0.0047 (6)
C120.0682 (13)0.0737 (14)0.0624 (12)0.0381 (12)0.0096 (10)0.0067 (11)
C130.0536 (10)0.0612 (12)0.0648 (12)0.0152 (9)0.0158 (9)0.0046 (10)
Geometric parameters (Å, º) top
N1—O21.220 (2)C4—C51.396 (2)
N1—O11.222 (2)C4—C71.471 (2)
N1—C11.470 (2)C5—C61.378 (2)
N2—C71.2811 (19)C5—H50.97 (2)
N2—O31.4117 (17)C6—H60.95 (2)
O3—C91.4353 (19)C7—C81.5090 (19)
O4—C101.3018 (19)C8—C101.5232 (19)
O4—C121.454 (2)C8—C91.532 (2)
O5—C101.1912 (19)C8—H80.947 (18)
O6—C111.1912 (19)C9—C111.523 (2)
O7—C111.330 (2)C9—H90.97 (2)
O7—C131.448 (2)C12—H1210.89 (3)
C1—C61.380 (2)C12—H1220.94 (3)
C1—C21.380 (2)C12—H1230.89 (3)
C2—C31.378 (2)C13—H1330.96 (3)
C2—H20.92 (2)C13—H1310.96 (3)
C3—C41.397 (2)C13—H1320.99 (3)
C3—H30.96 (2)
O2—N1—O1123.65 (16)C7—C8—C998.74 (11)
O2—N1—C1117.92 (16)C10—C8—C9110.33 (12)
O1—N1—C1118.43 (15)C7—C8—H8113.3 (10)
C7—N2—O3109.64 (12)C10—C8—H8105.5 (10)
N2—O3—C9107.65 (11)C9—C8—H8113.8 (10)
C10—O4—C12117.33 (14)O3—C9—C11109.59 (12)
C11—O7—C13116.52 (14)O3—C9—C8104.57 (11)
C6—C1—C2122.18 (14)C11—C9—C8114.41 (12)
C6—C1—N1118.86 (15)O3—C9—H9108.8 (11)
C2—C1—N1118.95 (14)C11—C9—H9106.7 (11)
C3—C2—C1118.81 (14)C8—C9—H9112.7 (11)
C3—C2—H2120.4 (12)O5—C10—O4124.97 (15)
C1—C2—H2120.8 (12)O5—C10—C8121.85 (14)
C2—C3—C4120.48 (15)O4—C10—C8113.16 (12)
C2—C3—H3120.4 (11)O6—C11—O7125.66 (15)
C4—C3—H3119.1 (11)O6—C11—C9124.89 (15)
C5—C4—C3119.20 (14)O7—C11—C9109.38 (12)
C5—C4—C7121.09 (13)O4—C12—H121111 (2)
C3—C4—C7119.71 (13)O4—C12—H122106.7 (19)
C6—C5—C4120.60 (14)H121—C12—H122108 (2)
C6—C5—H5119.5 (12)O4—C12—H123108 (2)
C4—C5—H5119.9 (12)H121—C12—H123115 (3)
C5—C6—C1118.72 (15)H122—C12—H123108 (2)
C5—C6—H6120.2 (12)O7—C13—H133105.6 (15)
C1—C6—H6121.0 (12)O7—C13—H131108.1 (15)
N2—C7—C4120.70 (13)H133—C13—H131114 (2)
N2—C7—C8113.07 (13)O7—C13—H132112.5 (17)
C4—C7—C8126.22 (13)H133—C13—H132111 (2)
C7—C8—C10115.36 (12)H131—C13—H132106 (2)

Experimental details

Crystal data
Chemical formulaC13H12N2O7
Mr308.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.2032 (2), 6.9183 (3), 27.515 (2)
β (°) 92.134 (4)
V3)1370.23 (12)
Z4
Radiation typeCu Kα
µ (mm1)1.07
Crystal size (mm)0.90 × 0.45 × 0.25
Data collection
DiffractometerBruker APEX-II CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2008)
Tmin, Tmax0.98, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
4957, 2596, 2490
Rint0.016
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.114, 1.05
No. of reflections2596
No. of parameters248
No. of restraints3
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXTL (Bruker, 2008), SHELXL2013 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

 

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