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The crystal structure of the title compound, C13H16N2O4, (1), reveals that the mol­ecule exists in the solid state in the equatorial conformation. Thus, the through-bond interaction present in the axial conformation is not strong enough to overcome the syn–diaxial interactions between the axial methyl substituent and the axial H atoms on each of the ring C atoms β to N. The C—OPNB (PNB is p-nitro­benzoate) bond distance is 1.4630 (16) Å, which is not significantly different from the corresponding C—OPNB distance in 4-tert-butyl­cyclo­hexyl 4-nitro­benzoate. The structure of (1) was determined at 130 K.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022407/dn6047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022407/dn6047Isup2.hkl
Contains datablock I

CCDC reference: 203012

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.097
  • Data-to-parameter ratio = 11.8

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 27.50 From the CIF: _reflns_number_total 2787 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3044 Completeness (_total/calc) 91.56% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C13H16N2O4Z = 2
Mr = 264.28F(000) = 280
Triclinic, P1Dx = 1.321 Mg m3
Hall symbol: -P 1Melting point: 93 K
a = 6.3348 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.697 (1) ÅCell parameters from 1094 reflections
c = 13.9423 (18) Åθ = 2.7–27.5°
α = 99.030 (2)°µ = 0.10 mm1
β = 92.142 (2)°T = 130 K
γ = 97.528 (3)°Plate, colourless
V = 664.43 (15) Å30.50 × 0.30 × 0.07 mm
Data collection top
Bruker CCD area-detector
diffractometer
1915 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 1.5°
φ and ω scansh = 84
3614 measured reflectionsk = 98
2787 independent reflectionsl = 1716
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097All H-atom parameters refined
S = 0.88 w = 1/[σ2(Fo2) + (0.0462P)2]
where P = (Fo2 + 2Fc2)/3
2787 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.19 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
C10.2048 (2)0.3072 (2)0.66782 (10)0.0273 (3)
H10.260 (2)0.4324 (19)0.6786 (9)0.026 (4)*
C20.0202 (2)0.2667 (2)0.59229 (10)0.0288 (3)
H2A0.092 (2)0.3469 (19)0.6126 (10)0.034 (4)*
H2B0.041 (2)0.1428 (19)0.5912 (10)0.032 (4)*
C30.0987 (2)0.2894 (2)0.49284 (10)0.0305 (4)
H3A0.020 (2)0.2537 (18)0.4443 (10)0.032 (4)*
H3B0.151 (2)0.4145 (18)0.4930 (9)0.024 (4)*
C40.4462 (2)0.2273 (2)0.53698 (11)0.0299 (3)
H4A0.510 (2)0.3587 (19)0.5389 (10)0.035 (4)*
H4B0.558 (2)0.1508 (18)0.5155 (10)0.032 (4)*
C50.3794 (2)0.1974 (2)0.63776 (11)0.0312 (4)
H5A0.325 (2)0.069 (2)0.6370 (10)0.034 (4)*
H5B0.505 (2)0.2232 (19)0.6840 (10)0.037 (4)*
C60.3289 (3)0.1980 (2)0.36842 (12)0.0375 (4)
H6A0.207 (3)0.155 (2)0.3204 (12)0.052 (5)*
H6B0.443 (3)0.125 (2)0.3498 (11)0.047 (5)*
H6C0.383 (2)0.325 (2)0.3606 (11)0.049 (5)*
C70.2210 (2)0.33825 (19)0.84218 (10)0.0301 (3)
C80.1023 (2)0.28964 (18)0.92706 (10)0.0281 (3)
C90.1065 (2)0.2015 (2)0.91485 (11)0.0341 (4)
H90.175 (2)0.167 (2)0.8494 (11)0.041 (4)*
C100.2151 (2)0.1644 (2)0.99466 (11)0.0356 (4)
H100.355 (3)0.107 (2)0.9889 (12)0.053 (5)*
C110.1135 (2)0.21507 (19)1.08604 (10)0.0306 (3)
C120.0934 (2)0.3020 (2)1.10049 (11)0.0332 (4)
H120.157 (2)0.337 (2)1.1658 (11)0.045 (4)*
C130.2006 (2)0.3385 (2)1.02006 (11)0.0319 (4)
H130.335 (2)0.398 (2)1.0292 (10)0.038 (4)*
N10.26463 (17)0.17903 (15)0.46569 (8)0.0274 (3)
N20.2311 (2)0.17568 (18)1.17124 (9)0.0380 (3)
O10.11629 (14)0.26353 (13)0.75790 (7)0.0313 (3)
O20.38872 (15)0.43602 (14)0.84938 (7)0.0424 (3)
O30.40037 (18)0.07581 (17)1.15680 (8)0.0597 (4)
O40.15396 (17)0.24315 (16)1.25239 (7)0.0466 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0263 (7)0.0277 (8)0.0269 (8)0.0008 (6)0.0029 (6)0.0046 (6)
C20.0226 (7)0.0332 (9)0.0311 (8)0.0046 (7)0.0017 (6)0.0057 (7)
C30.0266 (8)0.0363 (9)0.0297 (8)0.0062 (7)0.0011 (6)0.0079 (7)
C40.0231 (7)0.0310 (9)0.0353 (9)0.0041 (7)0.0021 (6)0.0041 (7)
C50.0259 (8)0.0367 (9)0.0309 (8)0.0044 (7)0.0027 (6)0.0061 (7)
C60.0385 (9)0.0438 (11)0.0330 (9)0.0119 (8)0.0071 (7)0.0088 (8)
C70.0275 (8)0.0317 (8)0.0289 (8)0.0004 (6)0.0019 (6)0.0032 (6)
C80.0272 (7)0.0265 (8)0.0291 (8)0.0015 (6)0.0004 (6)0.0020 (6)
C90.0329 (8)0.0388 (9)0.0268 (8)0.0051 (7)0.0022 (7)0.0025 (7)
C100.0292 (8)0.0410 (9)0.0327 (9)0.0068 (7)0.0003 (7)0.0042 (7)
C110.0323 (8)0.0322 (8)0.0269 (8)0.0028 (6)0.0041 (6)0.0046 (6)
C120.0330 (8)0.0368 (9)0.0275 (8)0.0005 (7)0.0041 (7)0.0032 (7)
C130.0249 (8)0.0349 (9)0.0328 (8)0.0027 (6)0.0018 (6)0.0030 (7)
N10.0260 (6)0.0306 (7)0.0259 (6)0.0060 (5)0.0023 (5)0.0038 (5)
N20.0382 (8)0.0441 (8)0.0303 (7)0.0004 (6)0.0026 (6)0.0061 (6)
O10.0292 (5)0.0362 (6)0.0256 (5)0.0051 (4)0.0015 (4)0.0042 (4)
O20.0334 (6)0.0542 (7)0.0330 (6)0.0143 (5)0.0002 (5)0.0037 (5)
O30.0500 (8)0.0795 (10)0.0394 (7)0.0255 (7)0.0085 (6)0.0060 (6)
O40.0445 (7)0.0666 (8)0.0262 (6)0.0024 (6)0.0003 (5)0.0046 (5)
Geometric parameters (Å, º) top
C1—O11.4630 (16)C6—H6B0.990 (16)
C1—C21.5111 (18)C6—H6C1.018 (17)
C1—C51.510 (2)C7—O21.2101 (16)
C1—H10.968 (14)C7—O11.3345 (15)
C2—C31.518 (2)C7—C81.496 (2)
C2—H2A1.019 (15)C8—C131.391 (2)
C2—H2B0.980 (14)C8—C91.3969 (19)
C3—N11.4603 (18)C9—C101.378 (2)
C3—H3A0.973 (14)C9—H90.978 (15)
C3—H3B0.976 (13)C10—C111.381 (2)
C4—N11.4616 (17)C10—H100.935 (16)
C4—C51.525 (2)C11—C121.3837 (19)
C4—H4A1.034 (14)C11—N21.4761 (18)
C4—H4B1.004 (14)C12—C131.380 (2)
C5—H5A1.001 (15)C12—H120.965 (15)
C5—H5B0.982 (14)C13—H130.906 (15)
C6—N11.4540 (19)N2—O41.2233 (15)
C6—H6A0.990 (16)N2—O31.2247 (15)
O1—C1—C2105.68 (10)H6A—C6—H6B107.1 (13)
O1—C1—C5111.02 (11)N1—C6—H6C114.0 (9)
C2—C1—C5110.75 (13)H6A—C6—H6C107.2 (12)
O1—C1—H1108.1 (8)H6B—C6—H6C107.5 (13)
C2—C1—H1110.8 (8)O2—C7—O1124.42 (13)
C5—C1—H1110.4 (8)O2—C7—C8124.05 (13)
C1—C2—C3110.17 (12)O1—C7—C8111.52 (11)
C1—C2—H2A109.1 (8)C13—C8—C9119.70 (14)
C3—C2—H2A111.9 (8)C13—C8—C7118.99 (12)
C1—C2—H2B107.0 (8)C9—C8—C7121.28 (12)
C3—C2—H2B109.4 (8)C10—C9—C8120.10 (14)
H2A—C2—H2B109.1 (12)C10—C9—H9120.3 (9)
N1—C3—C2111.64 (12)C8—C9—H9119.6 (9)
N1—C3—H3A107.9 (8)C9—C10—C11118.84 (14)
C2—C3—H3A109.1 (8)C9—C10—H10122.1 (10)
N1—C3—H3B110.6 (8)C11—C10—H10119.0 (10)
C2—C3—H3B109.2 (8)C10—C11—C12122.43 (14)
H3A—C3—H3B108.3 (11)C10—C11—N2118.55 (13)
N1—C4—C5110.73 (11)C12—C11—N2119.02 (12)
N1—C4—H4A110.0 (7)C13—C12—C11118.23 (13)
C5—C4—H4A110.0 (8)C13—C12—H12122.4 (9)
N1—C4—H4B107.8 (8)C11—C12—H12119.4 (9)
C5—C4—H4B109.9 (8)C12—C13—C8120.70 (14)
H4A—C4—H4B108.4 (11)C12—C13—H13118.6 (9)
C1—C5—C4109.53 (12)C8—C13—H13120.7 (9)
C1—C5—H5A109.0 (8)C6—N1—C3110.08 (12)
C4—C5—H5A110.3 (8)C6—N1—C4111.18 (12)
C1—C5—H5B113.1 (9)C3—N1—C4109.89 (12)
C4—C5—H5B109.8 (9)O4—N2—O3123.51 (13)
H5A—C5—H5B105.1 (11)O4—N2—C11118.41 (12)
N1—C6—H6A110.1 (9)O3—N2—C11118.08 (12)
N1—C6—H6B110.7 (9)C7—O1—C1118.26 (10)
O1—C1—C2—C3174.20 (12)N2—C11—C12—C13179.71 (14)
C5—C1—C2—C353.88 (17)C11—C12—C13—C80.3 (2)
C1—C2—C3—N156.30 (17)C9—C8—C13—C120.5 (2)
O1—C1—C5—C4172.16 (11)C7—C8—C13—C12177.51 (14)
C2—C1—C5—C455.07 (16)C2—C3—N1—C6177.42 (13)
N1—C4—C5—C158.72 (17)C2—C3—N1—C459.80 (15)
O2—C7—C8—C139.1 (2)C5—C4—N1—C6176.98 (13)
O1—C7—C8—C13172.31 (12)C5—C4—N1—C360.89 (16)
O2—C7—C8—C9168.93 (14)C10—C11—N2—O4169.27 (14)
O1—C7—C8—C99.7 (2)C12—C11—N2—O410.3 (2)
C13—C8—C9—C100.5 (2)C10—C11—N2—O311.3 (2)
C7—C8—C9—C10177.46 (14)C12—C11—N2—O3169.09 (14)
C8—C9—C10—C110.3 (2)O2—C7—O1—C12.4 (2)
C9—C10—C11—C120.1 (2)C8—C7—O1—C1176.18 (11)
C9—C10—C11—N2179.72 (14)C2—C1—O1—C7158.28 (12)
C10—C11—C12—C130.1 (2)C5—C1—O1—C781.57 (15)
 

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