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There are two independent mol­ecules, A and B, in the title compound, C16H18N4O4, and the asymmetric unit consists of one mol­ecule A and one half-mol­ecule B; a twofold axis runs through the centre of the N-N bond of mol­ecule B. The crystal structure is stabilized mainly by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026863/bt6721sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026863/bt6721Isup2.hkl
Contains datablock I

CCDC reference: 285500

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.047
  • wR factor = 0.107
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N5 - C23 .. 8.56 su
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.85 PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C18 .. 5.11 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 .. 5.74 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 25.00 From the CIF: _reflns_number_total 2550 Count of symmetry unique reflns 2551 Completeness (_total/calc) 99.96% 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 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; 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.

N,N'-Diethyl-4,4'-dinitrohydrazobenzene top
Crystal data top
C16H18N4O4F(000) = 1044
Mr = 330.34Dx = 1.343 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 60 reflections
a = 7.8212 (16) Åθ = 1.8–12.5°
b = 46.154 (4) ŵ = 0.10 mm1
c = 6.7885 (8) ÅT = 295 K
V = 2450.5 (6) Å3Prism, red
Z = 60.4 × 0.4 × 0.2 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.070
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.8°
Graphite monochromatorh = 99
ω scansk = 5454
6045 measured reflectionsl = 88
2550 independent reflections3 standard reflections every 97 reflections
1594 reflections with I > 2σ(I) intensity decay: none
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.001P)2 + P]
where P = (Fo2 + 2Fc2)/3
2550 reflections(Δ/σ)max < 0.001
325 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
O11.2281 (5)0.18667 (8)0.7748 (7)0.0920 (13)
O20.9552 (5)0.18962 (7)0.7215 (5)0.0701 (10)
O31.1594 (5)0.11903 (8)0.8338 (7)0.0874 (12)
O41.0551 (5)0.07597 (7)0.8584 (6)0.0897 (12)
O50.1050 (4)0.02616 (7)0.3721 (8)0.1032 (16)
O60.0890 (5)0.07220 (7)0.3956 (6)0.0867 (12)
N10.8269 (5)0.17853 (7)1.1264 (5)0.0486 (9)
N20.9069 (5)0.15309 (6)1.0533 (5)0.0484 (9)
N31.0841 (6)0.19364 (8)0.8239 (7)0.0626 (11)
N41.0409 (5)0.10215 (9)0.8367 (6)0.0620 (11)
N50.4406 (5)0.01142 (6)0.5341 (5)0.0536 (10)
N60.1678 (5)0.04976 (9)0.3700 (7)0.0650 (11)
C10.9351 (6)0.20235 (8)1.1463 (6)0.0495 (11)
C21.0632 (6)0.20944 (8)1.0108 (7)0.0536 (12)
C31.1743 (7)0.23244 (9)1.0352 (8)0.0662 (14)
H31.26100.23560.94390.079*
C41.1566 (8)0.25056 (10)1.1939 (9)0.0801 (17)
H41.22840.26651.20940.096*
C51.0311 (8)0.24478 (10)1.3294 (8)0.0753 (16)
H51.01800.25701.43740.090*
C60.9233 (7)0.22107 (8)1.3086 (7)0.0618 (13)
H60.84120.21751.40460.074*
C70.8112 (6)0.13925 (8)0.9041 (6)0.0443 (10)
C80.8675 (6)0.11420 (9)0.8068 (7)0.0505 (11)
C90.7706 (6)0.09950 (9)0.6694 (7)0.0594 (13)
H90.81170.08250.61240.071*
C100.6112 (6)0.11027 (10)0.6172 (7)0.0605 (13)
H100.54310.10050.52670.073*
C110.5553 (6)0.13579 (9)0.7021 (7)0.0564 (12)
H110.45090.14360.66360.068*
C120.6515 (6)0.14984 (9)0.8427 (6)0.0526 (11)
H120.60960.16680.89850.063*
C130.6882 (6)0.17443 (9)1.2737 (7)0.0615 (13)
H13A0.73610.17631.40490.074*
H13B0.64280.15501.26080.074*
C140.5432 (7)0.19596 (10)1.2512 (8)0.0766 (16)
H14A0.45810.19231.35010.115*
H14B0.49290.19391.12290.115*
H14C0.58670.21531.26640.115*
C150.9803 (6)0.13491 (9)1.2135 (7)0.0584 (12)
H15A0.99700.11541.16460.070*
H15B0.89960.13401.32170.070*
C161.1475 (7)0.14636 (9)1.2883 (9)0.0836 (18)
H16A1.19010.13381.38980.125*
H16B1.13110.16551.34090.125*
H16C1.22840.14711.18200.125*
C180.3525 (6)0.05239 (9)0.3234 (7)0.0510 (11)
C170.4751 (6)0.03327 (9)0.3972 (7)0.0478 (11)
C220.6404 (6)0.03630 (9)0.3168 (8)0.0581 (13)
H220.72600.02350.35570.070*
C210.6785 (7)0.05771 (9)0.1817 (8)0.0677 (14)
H210.78920.05920.13270.081*
C200.5547 (7)0.07711 (10)0.1177 (8)0.0657 (14)
H200.58120.09160.02760.079*
C190.3918 (6)0.07424 (9)0.1913 (8)0.0596 (13)
H190.30700.08710.15190.071*
C230.3415 (7)0.01775 (11)0.7190 (10)0.0856 (17)
H23A0.42040.02140.82640.103*
H23B0.27300.03500.69990.103*
C240.2283 (8)0.00690 (13)0.7707 (10)0.120 (2)
H24A0.16740.00250.88980.180*
H24B0.29600.02400.79000.180*
H24C0.14810.01010.66590.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.067 (3)0.108 (3)0.100 (3)0.004 (2)0.024 (3)0.014 (3)
O20.086 (3)0.076 (2)0.0490 (19)0.007 (2)0.001 (2)0.0062 (17)
O30.052 (2)0.095 (2)0.115 (3)0.004 (2)0.010 (3)0.007 (3)
O40.091 (3)0.068 (2)0.110 (3)0.020 (2)0.013 (3)0.006 (2)
O50.052 (2)0.068 (2)0.190 (5)0.0106 (18)0.002 (3)0.014 (3)
O60.069 (2)0.083 (2)0.108 (3)0.026 (2)0.018 (3)0.008 (2)
N10.056 (2)0.0481 (18)0.041 (2)0.0051 (19)0.002 (2)0.0003 (17)
N20.059 (2)0.0417 (17)0.0448 (19)0.0012 (18)0.005 (2)0.0008 (17)
N30.070 (3)0.057 (2)0.060 (3)0.006 (2)0.007 (3)0.003 (2)
N40.057 (3)0.066 (2)0.062 (3)0.003 (2)0.002 (2)0.006 (2)
N50.052 (2)0.0470 (19)0.062 (2)0.0108 (18)0.009 (2)0.0045 (18)
N60.057 (2)0.063 (2)0.075 (3)0.004 (2)0.008 (3)0.012 (2)
C10.055 (3)0.047 (2)0.047 (3)0.002 (2)0.008 (3)0.006 (2)
C20.061 (3)0.047 (2)0.053 (3)0.001 (2)0.001 (3)0.005 (2)
C30.063 (3)0.056 (3)0.080 (4)0.014 (3)0.006 (3)0.014 (3)
C40.088 (4)0.062 (3)0.091 (4)0.022 (3)0.020 (4)0.006 (3)
C50.097 (4)0.062 (3)0.067 (4)0.016 (3)0.015 (4)0.013 (3)
C60.080 (4)0.056 (2)0.049 (3)0.009 (3)0.004 (3)0.005 (2)
C70.048 (3)0.043 (2)0.042 (2)0.006 (2)0.002 (2)0.002 (2)
C80.051 (3)0.052 (2)0.049 (3)0.005 (2)0.003 (3)0.001 (2)
C90.063 (3)0.061 (3)0.055 (3)0.006 (2)0.006 (3)0.009 (3)
C100.059 (3)0.073 (3)0.049 (3)0.018 (3)0.003 (3)0.005 (3)
C110.049 (3)0.069 (3)0.051 (3)0.004 (2)0.006 (3)0.002 (3)
C120.051 (3)0.057 (2)0.050 (3)0.001 (2)0.005 (3)0.003 (2)
C130.070 (3)0.062 (3)0.052 (3)0.011 (3)0.011 (3)0.003 (2)
C140.070 (3)0.083 (3)0.077 (4)0.001 (3)0.016 (4)0.017 (3)
C150.069 (3)0.056 (2)0.051 (3)0.004 (2)0.010 (3)0.010 (2)
C160.089 (4)0.070 (3)0.092 (4)0.005 (3)0.045 (4)0.001 (3)
C180.045 (2)0.049 (2)0.059 (3)0.002 (2)0.002 (3)0.001 (2)
C170.046 (3)0.049 (2)0.049 (3)0.000 (2)0.003 (2)0.004 (2)
C220.048 (3)0.058 (3)0.069 (3)0.000 (2)0.001 (3)0.003 (3)
C210.062 (3)0.076 (3)0.065 (3)0.011 (3)0.012 (3)0.008 (3)
C200.071 (3)0.068 (3)0.058 (3)0.012 (3)0.004 (3)0.007 (3)
C190.063 (3)0.055 (2)0.061 (3)0.002 (2)0.010 (3)0.005 (3)
C230.066 (3)0.095 (4)0.096 (4)0.019 (3)0.010 (4)0.033 (4)
C240.100 (5)0.149 (6)0.110 (5)0.009 (5)0.019 (5)0.021 (5)
Geometric parameters (Å, º) top
O1—N31.218 (5)C10—H100.9300
O2—N31.239 (5)C11—C121.378 (6)
O3—N41.211 (5)C11—H110.9300
O4—N41.223 (4)C12—H120.9300
O5—N61.195 (4)C13—C141.516 (6)
O6—N61.218 (4)C13—H13A0.9700
N1—C11.394 (5)C13—H13B0.9700
N1—N21.420 (4)C14—H14A0.9600
N1—C131.487 (5)C14—H14B0.9600
N2—C71.412 (5)C14—H14C0.9600
N2—C151.489 (5)C15—C161.499 (7)
N3—C21.472 (6)C15—H15A0.9700
N4—C81.480 (6)C15—H15B0.9700
N5—C171.398 (5)C16—H16A0.9600
N5—N5i1.405 (6)C16—H16B0.9600
N5—C231.504 (7)C16—H16C0.9600
N6—C181.484 (6)C18—C191.384 (6)
C1—C21.399 (6)C18—C171.396 (6)
C1—C61.403 (6)C17—C221.411 (6)
C2—C31.382 (6)C22—C211.380 (6)
C3—C41.371 (7)C22—H220.9300
C3—H30.9300C21—C201.388 (7)
C4—C51.371 (7)C21—H210.9300
C4—H40.9300C20—C191.376 (7)
C5—C61.389 (6)C20—H200.9300
C5—H50.9300C19—H190.9300
C6—H60.9300C23—C241.484 (7)
C7—C81.402 (5)C23—H23A0.9700
C7—C121.405 (6)C23—H23B0.9700
C8—C91.380 (6)C24—H24A0.9600
C9—C101.388 (6)C24—H24B0.9600
C9—H90.9300C24—H24C0.9600
C10—C111.382 (6)
C1—N1—N2114.7 (3)N1—C13—C14113.3 (4)
C1—N1—C13118.6 (3)N1—C13—H13A108.9
N2—N1—C13116.8 (3)C14—C13—H13A108.9
C7—N2—N1113.0 (3)N1—C13—H13B108.9
C7—N2—C15118.2 (3)C14—C13—H13B108.9
N1—N2—C15112.4 (3)H13A—C13—H13B107.7
O1—N3—O2124.0 (5)C13—C14—H14A109.5
O1—N3—C2118.0 (5)C13—C14—H14B109.5
O2—N3—C2117.9 (4)H14A—C14—H14B109.5
O3—N4—O4124.6 (4)C13—C14—H14C109.5
O3—N4—C8117.2 (3)H14A—C14—H14C109.5
O4—N4—C8118.1 (4)H14B—C14—H14C109.5
C17—N5—N5i114.4 (3)N2—C15—C16112.7 (4)
C17—N5—C23120.9 (3)N2—C15—H15A109.1
N5i—N5—C23119.1 (2)C16—C15—H15A109.1
O5—N6—O6124.5 (4)N2—C15—H15B109.1
O5—N6—C18118.5 (4)C16—C15—H15B109.1
O6—N6—C18117.0 (4)H15A—C15—H15B107.8
N1—C1—C2123.8 (4)C15—C16—H16A109.5
N1—C1—C6121.5 (4)C15—C16—H16B109.5
C2—C1—C6114.8 (4)H16A—C16—H16B109.5
C3—C2—C1123.5 (5)C15—C16—H16C109.5
C3—C2—N3114.4 (5)H16A—C16—H16C109.5
C1—C2—N3122.0 (4)H16B—C16—H16C109.5
C4—C3—C2119.9 (5)C19—C18—C17122.7 (4)
C4—C3—H3120.0C19—C18—N6114.4 (4)
C2—C3—H3120.0C17—C18—N6122.7 (4)
C5—C4—C3118.7 (5)C18—C17—N5124.2 (4)
C5—C4—H4120.6C18—C17—C22115.3 (4)
C3—C4—H4120.6N5—C17—C22120.4 (4)
C4—C5—C6121.3 (5)C21—C22—C17121.7 (4)
C4—C5—H5119.4C21—C22—H22119.1
C6—C5—H5119.4C17—C22—H22119.1
C5—C6—C1121.7 (5)C22—C21—C20121.3 (5)
C5—C6—H6119.2C22—C21—H21119.4
C1—C6—H6119.2C20—C21—H21119.4
C8—C7—C12115.2 (4)C19—C20—C21118.0 (5)
C8—C7—N2123.0 (4)C19—C20—H20121.0
C12—C7—N2121.8 (4)C21—C20—H20121.0
C9—C8—C7123.5 (4)C20—C19—C18120.7 (5)
C9—C8—N4114.3 (4)C20—C19—H19119.6
C7—C8—N4122.2 (4)C18—C19—H19119.6
C8—C9—C10119.3 (4)C24—C23—N5110.9 (5)
C8—C9—H9120.3C24—C23—H23A109.5
C10—C9—H9120.3N5—C23—H23A109.5
C11—C10—C9118.9 (5)C24—C23—H23B109.5
C11—C10—H10120.6N5—C23—H23B109.5
C9—C10—H10120.6H23A—C23—H23B108.1
C12—C11—C10121.1 (5)C23—C24—H24A109.5
C12—C11—H11119.4C23—C24—H24B109.5
C10—C11—H11119.4H24A—C24—H24B109.5
C11—C12—C7121.9 (4)C23—C24—H24C109.5
C11—C12—H12119.1H24A—C24—H24C109.5
C7—C12—H12119.1H24B—C24—H24C109.5
C1—N1—N2—C7134.4 (4)O4—N4—C8—C7135.8 (4)
C13—N1—N2—C780.3 (4)C7—C8—C9—C102.5 (7)
C1—N1—N2—C1588.7 (4)N4—C8—C9—C10174.7 (4)
C13—N1—N2—C1556.7 (5)C8—C9—C10—C111.2 (7)
N2—N1—C1—C239.3 (5)C9—C10—C11—C122.9 (7)
C13—N1—C1—C2176.0 (4)C10—C11—C12—C71.0 (7)
N2—N1—C1—C6140.1 (4)C8—C7—C12—C112.4 (6)
C13—N1—C1—C64.6 (6)N2—C7—C12—C11177.7 (4)
N1—C1—C2—C3177.5 (4)C1—N1—C13—C1472.6 (5)
C6—C1—C2—C32.0 (7)N2—N1—C13—C14143.5 (4)
N1—C1—C2—N35.8 (7)C7—N2—C15—C16147.1 (4)
C6—C1—C2—N3174.7 (4)N1—N2—C15—C1678.4 (5)
O1—N3—C2—C347.8 (6)O5—N6—C18—C19135.0 (5)
O2—N3—C2—C3128.5 (5)O6—N6—C18—C1942.0 (7)
O1—N3—C2—C1135.2 (5)O5—N6—C18—C1741.3 (7)
O2—N3—C2—C148.5 (6)O6—N6—C18—C17141.8 (5)
C1—C2—C3—C43.3 (7)C19—C18—C17—N5178.5 (4)
N3—C2—C3—C4173.6 (5)N6—C18—C17—N55.6 (7)
C2—C3—C4—C52.1 (8)C19—C18—C17—C224.6 (6)
C3—C4—C5—C60.2 (8)N6—C18—C17—C22171.4 (4)
C4—C5—C6—C11.4 (8)N5i—N5—C17—C18157.5 (4)
N1—C1—C6—C5179.8 (4)C23—N5—C17—C1848.9 (6)
C2—C1—C6—C50.4 (7)N5i—N5—C17—C2219.3 (6)
N1—N2—C7—C8178.2 (4)C23—N5—C17—C22134.3 (5)
C15—N2—C7—C847.5 (6)C18—C17—C22—C213.1 (6)
N1—N2—C7—C121.7 (5)N5—C17—C22—C21179.8 (4)
C15—N2—C7—C12132.6 (4)C17—C22—C21—C200.6 (7)
C12—C7—C8—C94.2 (6)C22—C21—C20—C190.6 (7)
N2—C7—C8—C9175.9 (4)C21—C20—C19—C180.8 (7)
C12—C7—C8—N4172.8 (4)C17—C18—C19—C203.6 (7)
N2—C7—C8—N47.1 (6)N6—C18—C19—C20172.6 (5)
O3—N4—C8—C9131.6 (5)C17—N5—C23—C24143.3 (5)
O4—N4—C8—C946.9 (6)N5i—N5—C23—C2464.3 (6)
O3—N4—C8—C745.6 (7)
Symmetry code: (i) x+1, y, z.
 

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