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The title compound, C16H21N5O6, is a chiral β-nitro azo compound prepared in the reaction of a chiral menthone hydrazone with nitric oxide in dichloro­methane. The mol­ecule adopts a trans configuration with respect to the N=N double bond. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into coupled chains extending along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015078/cv2033sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015078/cv2033Isup2.hkl
Contains datablock I

CCDC reference: 241117

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.038
  • wR factor = 0.087
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.49 From the CIF: _reflns_number_total 2049 Count of symmetry unique reflns 2049 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(E)-1-(2,4-Dinitrophenyl)-2-(2-isopropyl-5-methyl-1-nitrocyclohexyl)diazene top
Crystal data top
C16H21N5O6F(000) = 400
Mr = 379.38Dx = 1.352 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.419 (2) ÅCell parameters from 34 reflections
b = 9.382 (2) Åθ = 3.3–16.8°
c = 12.366 (4) ŵ = 0.11 mm1
β = 107.46 (2)°T = 298 K
V = 931.8 (4) Å3Block, orange
Z = 20.49 × 0.37 × 0.20 mm
Data collection top
Siemens P4
diffractometer
1333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 26.5°, θmin = 1.7°
ω scansh = 010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 011
Tmin = 0.950, Tmax = 0.979l = 1514
2185 measured reflections3 standard reflections every 97 reflections
2049 independent reflections intensity decay: 1.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0446P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
2049 reflectionsΔρmax = 0.13 e Å3
248 parametersΔρmin = 0.13 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (4)
Special details top

Experimental. Elemental analysis: found: C 50.14, H 5.71, N 18.52%; calculated for C16H21N5O6: C 50.36, H 5.58, N 18.46%.

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
O10.6632 (3)0.4596 (3)0.8362 (2)0.0691 (7)
O20.5196 (3)0.3440 (3)0.6910 (2)0.0938 (10)
O30.8438 (3)0.2093 (3)0.7821 (3)0.1009 (11)
O40.8006 (3)0.3800 (3)0.6614 (3)0.0917 (9)
O50.2162 (4)0.5155 (4)0.5212 (3)0.1077 (11)
O60.0279 (3)0.3551 (4)0.5040 (3)0.1098 (11)
N10.6308 (3)0.3521 (3)0.7796 (2)0.0518 (7)
N20.7577 (4)0.2747 (3)0.7003 (3)0.0669 (8)
N30.1724 (4)0.3935 (5)0.5292 (2)0.0760 (10)
N40.6700 (3)0.0249 (3)0.7009 (2)0.0503 (7)
N50.6277 (3)0.1048 (3)0.7663 (2)0.0474 (6)
C10.7447 (3)0.2211 (3)0.8149 (2)0.0411 (7)
C20.8026 (3)0.2075 (3)0.9449 (2)0.0424 (7)
H20.85380.29920.97390.051*
C30.9427 (3)0.0970 (4)0.9787 (2)0.0519 (8)
H3A0.98070.08781.06060.062*
H3B0.90030.00510.94700.062*
C41.0884 (3)0.1395 (4)0.9368 (3)0.0567 (9)
H4A1.13180.23060.96960.068*
H4B1.17640.06930.96200.068*
C51.0377 (3)0.1504 (4)0.8087 (3)0.0542 (9)
H51.00590.05530.77670.065*
C60.8880 (4)0.2493 (4)0.7662 (3)0.0500 (8)
H6A0.92540.34670.78380.060*
H6B0.84610.24130.68430.060*
C71.1821 (4)0.2044 (5)0.7682 (3)0.0796 (13)
H7A1.21420.29800.79840.119*
H7B1.14750.20840.68690.119*
H7C1.27510.14080.79400.119*
C80.6610 (4)0.1838 (4)0.9999 (3)0.0506 (8)
H80.56350.23750.95530.061*
C90.6087 (4)0.0287 (4)1.0020 (3)0.0752 (11)
H9A0.51390.02321.02970.113*
H9B0.69910.02491.05100.113*
H9C0.58030.00990.92680.113*
C100.7125 (4)0.2438 (5)1.1195 (3)0.0748 (12)
H10A0.80900.19391.16490.112*
H10B0.62290.23211.15180.112*
H10C0.73800.34331.11720.112*
C110.5439 (4)0.0826 (4)0.6562 (2)0.0461 (8)
C120.5847 (4)0.2250 (4)0.6520 (2)0.0481 (8)
C130.4649 (4)0.3269 (4)0.6076 (2)0.0541 (9)
H130.49330.42220.60430.065*
C140.3024 (4)0.2828 (4)0.5686 (2)0.0539 (8)
C150.2572 (4)0.1428 (4)0.5684 (3)0.0581 (9)
H150.14610.11580.53990.070*
C160.3793 (4)0.0424 (4)0.6110 (2)0.0562 (9)
H160.35070.05350.60930.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0880 (17)0.0513 (15)0.0662 (15)0.0156 (14)0.0206 (13)0.0040 (14)
O20.0793 (18)0.0657 (18)0.097 (2)0.0042 (16)0.0333 (16)0.0120 (17)
O30.0649 (16)0.085 (2)0.116 (2)0.0099 (16)0.0292 (16)0.0191 (19)
O40.0740 (17)0.080 (2)0.120 (2)0.0186 (17)0.0270 (15)0.0200 (19)
O50.114 (3)0.075 (2)0.109 (2)0.033 (2)0.0045 (18)0.003 (2)
O60.0606 (17)0.126 (3)0.128 (2)0.037 (2)0.0058 (15)0.003 (2)
N10.0484 (16)0.0487 (17)0.0568 (17)0.0039 (14)0.0136 (14)0.0083 (16)
N20.0545 (17)0.0568 (19)0.082 (2)0.0030 (18)0.0093 (15)0.0006 (19)
N30.070 (2)0.086 (3)0.0591 (19)0.025 (2)0.0007 (16)0.013 (2)
N40.0461 (14)0.0556 (17)0.0462 (14)0.0004 (14)0.0093 (12)0.0044 (14)
N50.0422 (14)0.0478 (16)0.0475 (15)0.0002 (13)0.0063 (12)0.0038 (13)
C10.0397 (15)0.0373 (16)0.0443 (16)0.0026 (15)0.0099 (12)0.0012 (15)
C20.0413 (15)0.0426 (18)0.0419 (16)0.0004 (14)0.0103 (12)0.0017 (15)
C30.0431 (17)0.056 (2)0.0527 (18)0.0028 (17)0.0084 (14)0.0072 (17)
C40.0358 (15)0.067 (2)0.063 (2)0.0059 (17)0.0087 (13)0.0021 (18)
C50.0393 (16)0.062 (2)0.061 (2)0.0009 (16)0.0149 (14)0.0096 (17)
C60.0455 (17)0.056 (2)0.0487 (17)0.0043 (16)0.0151 (13)0.0005 (16)
C70.0498 (18)0.121 (4)0.075 (2)0.008 (2)0.0299 (16)0.019 (3)
C80.0418 (16)0.061 (2)0.0502 (18)0.0012 (16)0.0157 (13)0.0030 (16)
C90.075 (2)0.076 (3)0.085 (3)0.008 (2)0.039 (2)0.010 (2)
C100.072 (2)0.103 (3)0.057 (2)0.004 (2)0.0305 (17)0.006 (2)
C110.0439 (18)0.050 (2)0.0401 (17)0.0027 (16)0.0065 (14)0.0021 (15)
C120.0458 (17)0.054 (2)0.0420 (17)0.0022 (16)0.0088 (14)0.0001 (15)
C130.062 (2)0.050 (2)0.0447 (18)0.0045 (17)0.0066 (15)0.0004 (16)
C140.0507 (18)0.066 (2)0.0383 (16)0.0126 (19)0.0036 (13)0.0009 (17)
C150.0402 (17)0.073 (3)0.052 (2)0.0006 (19)0.0007 (14)0.0046 (19)
C160.0491 (19)0.060 (2)0.0538 (19)0.0039 (18)0.0067 (15)0.0058 (18)
Geometric parameters (Å, º) top
O1—N11.211 (3)C5—H50.9800
O2—N11.211 (3)C6—H6A0.9700
O3—N21.219 (4)C6—H6B0.9700
O4—N21.201 (4)C7—H7A0.9600
O5—N31.215 (4)C7—H7B0.9600
O6—N31.216 (4)C7—H7C0.9600
N1—C11.540 (4)C8—C101.519 (4)
N2—C121.475 (4)C8—C91.523 (5)
N3—C141.481 (5)C8—H80.9800
N4—N51.231 (3)C9—H9A0.9600
N4—C111.449 (4)C9—H9B0.9600
N5—C11.472 (4)C9—H9C0.9600
C1—C61.525 (4)C10—H10A0.9600
C1—C21.539 (4)C10—H10B0.9600
C2—C31.531 (4)C10—H10C0.9600
C2—C81.555 (4)C11—C161.382 (4)
C2—H20.9800C11—C121.384 (4)
C3—C41.521 (4)C12—C131.378 (4)
C3—H3A0.9700C13—C141.371 (4)
C3—H3B0.9700C13—H130.9300
C4—C51.516 (4)C14—C151.368 (5)
C4—H4A0.9700C15—C161.377 (4)
C4—H4B0.9700C15—H150.9300
C5—C61.526 (4)C16—H160.9300
C5—C71.533 (4)
O2—N1—O1123.6 (3)C5—C6—H6B108.4
O2—N1—C1117.0 (3)H6A—C6—H6B107.5
O1—N1—C1119.2 (2)C5—C7—H7A109.5
O4—N2—O3124.8 (3)C5—C7—H7B109.5
O4—N2—C12118.5 (3)H7A—C7—H7B109.5
O3—N2—C12116.5 (3)C5—C7—H7C109.5
O5—N3—O6124.3 (4)H7A—C7—H7C109.5
O5—N3—C14118.3 (4)H7B—C7—H7C109.5
O6—N3—C14117.4 (4)C10—C8—C9109.7 (3)
N5—N4—C11110.6 (2)C10—C8—C2109.9 (2)
N4—N5—C1115.4 (2)C9—C8—C2114.1 (3)
N5—C1—C6118.6 (3)C10—C8—H8107.7
N5—C1—C2109.2 (2)C9—C8—H8107.7
C6—C1—C2112.8 (2)C2—C8—H8107.7
N5—C1—N1101.1 (2)C8—C9—H9A109.5
C6—C1—N1104.4 (2)C8—C9—H9B109.5
C2—C1—N1109.7 (2)H9A—C9—H9B109.5
C3—C2—C1108.5 (2)C8—C9—H9C109.5
C3—C2—C8114.3 (2)H9A—C9—H9C109.5
C1—C2—C8115.1 (2)H9B—C9—H9C109.5
C3—C2—H2106.0C8—C10—H10A109.5
C1—C2—H2106.0C8—C10—H10B109.5
C8—C2—H2106.0H10A—C10—H10B109.5
C4—C3—C2111.3 (3)C8—C10—H10C109.5
C4—C3—H3A109.4H10A—C10—H10C109.5
C2—C3—H3A109.4H10B—C10—H10C109.5
C4—C3—H3B109.4C16—C11—C12118.6 (3)
C2—C3—H3B109.4C16—C11—N4119.7 (3)
H3A—C3—H3B108.0C12—C11—N4121.6 (3)
C5—C4—C3111.8 (2)C13—C12—C11121.6 (3)
C5—C4—H4A109.3C13—C12—N2117.2 (3)
C3—C4—H4A109.3C11—C12—N2121.1 (3)
C5—C4—H4B109.3C14—C13—C12117.7 (3)
C3—C4—H4B109.3C14—C13—H13121.2
H4A—C4—H4B107.9C12—C13—H13121.2
C4—C5—C6110.2 (2)C15—C14—C13122.5 (3)
C4—C5—C7111.2 (2)C15—C14—N3119.7 (3)
C6—C5—C7109.9 (3)C13—C14—N3117.7 (4)
C4—C5—H5108.5C14—C15—C16118.7 (3)
C6—C5—H5108.5C14—C15—H15120.6
C7—C5—H5108.5C16—C15—H15120.6
C1—C6—C5115.3 (3)C15—C16—C11120.7 (3)
C1—C6—H6A108.4C15—C16—H16119.6
C5—C6—H6A108.4C11—C16—H16119.6
C1—C6—H6B108.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.423.244 (5)147
C7—H7B···O6ii0.962.453.346 (5)155
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1.
 

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