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The title compound [systematic name: (4-di­methyl­amino­phenyl)(4-nitro­phenyl)­diazene], C14H14N4O2, has trans geometry about the azo linkage and is planar. Although the crystal structure is non-centrosymmetric, the overall net dipole moment is minimized by antiparallel arrangement of chains of mol­ecules related by translation (1 + x, y, 2 + z) and by marked orientational disorder in the azo moiety, through rotation about the C...C axis that it bridges. The chains are connected by weak C—H...O hydrogen bonding between nitro and di­methyl­amino groups. They lie perpendicular to the (103) plane and form stacks through π–π interaction, propagating along the crystallographic a axis. The stacks interact through a combination of van der Waals interactions and edge-to-face π–π interaction to give a herring-bone appearance in the view along their long axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400159X/cf6323sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680400159X/cf6323Isup2.hkl
Contains datablock I

CCDC reference: 234915

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](Please check) = 0.000 Å
  • R factor = 0.071
  • wR factor = 0.204
  • Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level A ATOM007_ALERT_1_A _atom_site_aniso_label is missing Unique label identifying the atom site. PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ..... = 20
Alert level B PLAT210_ALERT_3_B No Anisotropic ADP's Found in CIF .............. ? PLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 24 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
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 27.45 From the CIF: _reflns_number_total 1507 Count of symmetry unique reflns 1540 Completeness (_total/calc) 97.86% 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
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (CCDC, 2003).

(I) top
Crystal data top
C14H14N4O2F(000) = 284
Mr = 270.29Dx = 1.409 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.590 (4) ÅCell parameters from 2320 reflections
b = 10.532 (6) Åθ = 5.1–53.2°
c = 8.101 (4) ŵ = 0.10 mm1
β = 100.248 (9)°T = 150 K
V = 637.3 (6) Å3Block, red
Z = 20.43 × 0.42 × 0.19 mm
Data collection top
Bruker SMART 1000
diffractometer
1507 independent reflections
Radiation source: fine-focus sealed tube1202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 100 pixels mm-1θmax = 27.5°, θmin = 2.6°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
k = 1313
Tmin = 0.959, Tmax = 0.982l = 1010
6858 measured reflections
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.1146P)2 + 0.2904P]
where P = (Fo2 + 2Fc2)/3
1183 reflections(Δ/σ)max < 0.001
119 parametersΔρmax = 0.37 e Å3
86 restraintsΔρmin = 0.33 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*/UeqOcc. (<1)
O10.0061 (7)0.2154 (6)0.1419 (7)0.0453 (15)*0.750 (5)
O20.0563 (8)0.4133 (6)0.1875 (7)0.0375 (15)*0.750 (5)
O1'0.043 (2)0.2321 (12)0.179 (2)0.039 (3)*0.250 (5)
O2'0.099 (2)0.4343 (12)0.182 (2)0.037 (4)*0.250 (5)
N10.4333 (6)0.2907 (6)0.6621 (6)0.0256 (11)*0.750 (5)
N20.4342 (6)0.3848 (6)0.5666 (7)0.0269 (11)*0.750 (5)
N30.7734 (7)0.3179 (6)1.3252 (6)0.0256 (12)*0.750 (5)
N40.0665 (8)0.3200 (5)0.0958 (6)0.0270 (13)*0.750 (5)
C10.1531 (8)0.3330 (6)0.0757 (4)0.0278 (11)*0.750 (5)
C20.2433 (8)0.4456 (6)0.1240 (5)0.0286 (11)*0.750 (5)
H2B0.24210.51260.04530.034*0.750 (5)
C30.3351 (6)0.4601 (6)0.2874 (5)0.0280 (11)*0.750 (5)
H3A0.39670.53710.32040.034*0.750 (5)
C40.3367 (6)0.3621 (7)0.4024 (4)0.0278 (11)*0.750 (5)
C50.2466 (6)0.2495 (6)0.3542 (5)0.0295 (12)*0.750 (5)
H5A0.24770.18240.43280.035*0.750 (5)
C60.1548 (7)0.2350 (6)0.1908 (5)0.0304 (11)*0.750 (5)
H6A0.09320.15800.15780.037*0.750 (5)
C70.5273 (6)0.3079 (5)0.8256 (4)0.0257 (11)*0.750 (5)
C80.6257 (6)0.4151 (5)0.8843 (6)0.0248 (11)*0.750 (5)
H8A0.63350.48440.81100.030*0.750 (5)
C90.7127 (7)0.4208 (6)1.0503 (6)0.0256 (11)*0.750 (5)
H9A0.78000.49411.09040.031*0.750 (5)
C100.7013 (9)0.3194 (7)1.1576 (5)0.0244 (10)*0.750 (5)
C110.6029 (9)0.2122 (6)1.0990 (6)0.0292 (11)*0.750 (5)
H11A0.59510.14281.17230.035*0.750 (5)
C120.5159 (7)0.2064 (5)0.9330 (6)0.0294 (11)*0.750 (5)
H12A0.44860.13320.89290.035*0.750 (5)
C130.8565 (9)0.4323 (7)1.4038 (8)0.0304 (17)*0.750 (5)
H13A0.77440.50421.37670.046*0.750 (5)
H13B0.96760.44931.36190.046*0.750 (5)
H13C0.88350.42061.52570.046*0.750 (5)
C140.7697 (11)0.2036 (8)1.4249 (10)0.0372 (18)*0.750 (5)
H14A0.81190.13141.36630.056*0.750 (5)
H14B0.64700.18751.44170.056*0.750 (5)
H14C0.84780.21481.53400.056*0.750 (5)
N1'0.4720 (18)0.3616 (15)0.6421 (17)0.0277 (18)*0.250 (5)
N2'0.3756 (18)0.2716 (14)0.5709 (16)0.0264 (17)*0.250 (5)
N3'0.810 (2)0.3319 (13)1.3125 (17)0.025 (2)*0.250 (5)
N4'0.097 (2)0.3320 (10)0.1105 (16)0.026 (2)*0.250 (5)
C1'0.161 (2)0.3322 (16)0.0630 (11)0.0289 (15)*0.250 (5)
C2'0.259 (2)0.4299 (13)0.1506 (15)0.0299 (14)*0.250 (5)
H2'B0.27750.50700.09500.036*0.250 (5)
C3'0.3313 (18)0.4149 (13)0.3197 (15)0.0289 (15)*0.250 (5)
H3'A0.39840.48170.37960.035*0.250 (5)
C4'0.3048 (18)0.3021 (15)0.4010 (10)0.0293 (16)*0.250 (5)
C5'0.2066 (18)0.2044 (13)0.3134 (15)0.0289 (16)*0.250 (5)
H5'A0.18850.12730.36900.035*0.250 (5)
C6'0.135 (2)0.2194 (14)0.1443 (15)0.0297 (16)*0.250 (5)
H6'A0.06760.15260.08440.036*0.250 (5)
C7'0.5515 (19)0.3374 (14)0.8102 (12)0.0254 (16)*0.250 (5)
C8'0.6624 (19)0.4338 (12)0.8860 (17)0.0245 (15)*0.250 (5)
H8'A0.68490.50610.82270.029*0.250 (5)
C9'0.740 (2)0.4245 (17)1.0543 (18)0.0255 (14)*0.250 (5)
H9'A0.81610.49041.10610.031*0.250 (5)
C10'0.707 (3)0.319 (2)1.1469 (14)0.0266 (14)*0.250 (5)
C11'0.597 (3)0.2223 (16)1.0712 (17)0.0277 (14)*0.250 (5)
H11B0.57400.15001.13440.033*0.250 (5)
C12'0.519 (2)0.2316 (13)0.9028 (16)0.0275 (15)*0.250 (5)
H12B0.44280.16570.85110.033*0.250 (5)
C13'0.883 (3)0.4539 (14)1.374 (3)0.029 (4)*0.250 (5)
H13D0.95670.44291.48560.043*0.250 (5)
H13E0.78550.51311.38130.043*0.250 (5)
H13F0.95760.48781.29710.043*0.250 (5)
C14'0.805 (3)0.2314 (19)1.434 (3)0.029 (4)*0.250 (5)
H14D0.84030.26561.54790.044*0.250 (5)
H14E0.88750.16361.41600.044*0.250 (5)
H14F0.68300.19721.42140.044*0.250 (5)
Geometric parameters (Å, º) top
O1—N41.226 (4)C14—H14B0.980
O2—N41.226 (4)C14—H14C0.980
O1'—N4'1.226 (4)N1'—N2'1.271 (15)
O2'—N4'1.226 (4)N1'—C7'1.412 (14)
N1—N21.258 (6)N2'—C4'1.422 (13)
N1—C71.400 (5)N3'—C10'1.432 (13)
N2—C41.422 (6)N3'—C14'1.453 (5)
N3—C101.371 (5)N3'—C13'1.453 (5)
N3—C131.453 (5)N4'—C1'1.403 (13)
N3—C141.453 (5)C1'—C2'1.390
N4—C11.434 (5)C1'—C6'1.390
C1—C21.390C2'—C3'1.390
C1—C61.390C2'—H2'B0.950
C2—C31.390C3'—C4'1.390
C2—H2B0.950C3'—H3'A0.950
C3—C41.390C4'—C5'1.390
C3—H3A0.950C5'—C6'1.390
C4—C51.390C5'—H5'A0.950
C5—C61.390C6'—H6'A0.950
C5—H5A0.950C7'—C8'1.390
C6—H6A0.950C7'—C12'1.390
C7—C81.390C8'—C9'1.390
C7—C121.390C8'—H8'A0.950
C8—C91.390C9'—C10'1.390
C8—H8A0.950C9'—H9'A0.950
C9—C101.390C10'—C11'1.390
C9—H9A0.950C11'—C12'1.390
C10—C111.390C11'—H11B0.950
C11—C121.390C12'—H12B0.950
C11—H11A0.950C13'—H13D0.980
C12—H12A0.950C13'—H13E0.980
C13—H13A0.980C13'—H13F0.980
C13—H13B0.980C14'—H14D0.980
C13—H13C0.980C14'—H14E0.980
C14—H14A0.980C14'—H14F0.980
N2—N1—C7115.0 (5)O2'—N4'—C1'116.3 (13)
N1—N2—C4112.5 (4)O1'—N4'—C1'119.0 (13)
C10—N3—C13119.4 (5)C2'—C1'—C6'120.0
C10—N3—C14121.0 (5)C2'—C1'—N4'124.9 (11)
C13—N3—C14119.6 (5)C6'—C1'—N4'114.8 (11)
O2—N4—O1123.7 (5)C1'—C2'—C3'120.0
O2—N4—C1118.6 (5)C1'—C2'—H2'B120.0
O1—N4—C1117.6 (4)C3'—C2'—H2'B120.0
C2—C1—C6120.0C2'—C3'—C4'120.0
C2—C1—N4118.2 (3)C2'—C3'—H3'A120.0
C6—C1—N4121.8 (3)C4'—C3'—H3'A120.0
C1—C2—C3120.0C5'—C4'—C3'120.0
C1—C2—H2B120.0C5'—C4'—N2'113.8 (11)
C3—C2—H2B120.0C3'—C4'—N2'126.2 (11)
C2—C3—C4120.0C6'—C5'—C4'120.0
C2—C3—H3A120.0C6'—C5'—H5'A120.0
C4—C3—H3A120.0C4'—C5'—H5'A120.0
C5—C4—C3120.0C5'—C6'—C1'120.0
C5—C4—N2123.7 (3)C5'—C6'—H6'A120.0
C3—C4—N2116.3 (3)C1'—C6'—H6'A120.0
C6—C5—C4120.0C8'—C7'—C12'120.0
C6—C5—H5A120.0C8'—C7'—N1'114.5 (11)
C4—C5—H5A120.0C12'—C7'—N1'125.3 (11)
C5—C6—C1120.0C7'—C8'—C9'120.0
C5—C6—H6A120.0C7'—C8'—H8'A120.0
C1—C6—H6A120.0C9'—C8'—H8'A120.0
C8—C7—C12120.0C10'—C9'—C8'120.0
C8—C7—N1125.5 (3)C10'—C9'—H9'A120.0
C12—C7—N1114.5 (3)C8'—C9'—H9'A120.0
C7—C8—C9120.0C9'—C10'—C11'120.0
C7—C8—H8A120.0C9'—C10'—N3'107.9 (13)
C9—C8—H8A120.0C11'—C10'—N3'132.0 (13)
C8—C9—C10120.0C12'—C11'—C10'120.0
C8—C9—H9A120.0C12'—C11'—H11B120.0
C10—C9—H9A120.0C10'—C11'—H11B120.0
N3—C10—C11115.2 (4)C11'—C12'—C7'120.0
N3—C10—C9124.7 (4)C11'—C12'—H12B120.0
C11—C10—C9120.0C7'—C12'—H12B120.0
C12—C11—C10120.0N3'—C13'—H13D109.5
C12—C11—H11A120.0N3'—C13'—H13E109.5
C10—C11—H11A120.0H13D—C13'—H13E109.5
C11—C12—C7120.0N3'—C13'—H13F109.5
C11—C12—H12A120.0H13D—C13'—H13F109.5
C7—C12—H12A120.0H13E—C13'—H13F109.5
N2'—N1'—C7'114.6 (14)N3'—C14'—H14D109.5
N1'—N2'—C4'111.0 (13)N3'—C14'—H14E109.5
C10'—N3'—C14'119.4 (15)H14D—C14'—H14E109.5
C10'—N3'—C13'121.3 (15)N3'—C14'—H14F109.5
C14'—N3'—C13'117.7 (16)H14D—C14'—H14F109.5
O2'—N4'—O1'124.8 (15)H14E—C14'—H14F109.5
C7—N1—N2—C4180.0 (4)C7'—N1'—N2'—C4'178.4 (13)
O2—N4—C1—C28.9 (8)O2'—N4'—C1'—C2'14 (3)
O1—N4—C1—C2171.4 (5)O1'—N4'—C1'—C2'165.8 (15)
O2—N4—C1—C6173.8 (5)O2'—N4'—C1'—C6'171.7 (15)
O1—N4—C1—C65.9 (8)O1'—N4'—C1'—C6'8 (2)
C6—C1—C2—C30.0C6'—C1'—C2'—C3'0.0
N4—C1—C2—C3177.4 (6)N4'—C1'—C2'—C3'174 (2)
C1—C2—C3—C40.0C1'—C2'—C3'—C4'0.0
C2—C3—C4—C50.0C2'—C3'—C4'—C5'0.0
C2—C3—C4—N2179.9 (4)C2'—C3'—C4'—N2'177.4 (15)
N1—N2—C4—C51.6 (6)N1'—N2'—C4'—C5'176.5 (11)
N1—N2—C4—C3178.3 (3)N1'—N2'—C4'—C3'1.1 (18)
C3—C4—C5—C60.0C3'—C4'—C5'—C6'0.0
N2—C4—C5—C6179.8 (5)N2'—C4'—C5'—C6'177.7 (13)
C4—C5—C6—C10.0C4'—C5'—C6'—C1'0.0
C2—C1—C6—C50.0C2'—C1'—C6'—C5'0.0
N4—C1—C6—C5177.3 (6)N4'—C1'—C6'—C5'174.3 (18)
N2—N1—C7—C83.6 (6)N2'—N1'—C7'—C8'177.6 (12)
N2—N1—C7—C12176.1 (4)N2'—N1'—C7'—C12'6.3 (19)
C12—C7—C8—C90.0C12'—C7'—C8'—C9'0.0
N1—C7—C8—C9179.7 (5)N1'—C7'—C8'—C9'176.3 (15)
C7—C8—C9—C100.0C7'—C8'—C9'—C10'0.0
C13—N3—C10—C11171.3 (5)C8'—C9'—C10'—C11'0.0
C14—N3—C10—C119.4 (8)C8'—C9'—C10'—N3'177.6 (19)
C13—N3—C10—C95.1 (9)C14'—N3'—C10'—C9'177.8 (15)
C14—N3—C10—C9174.2 (5)C13'—N3'—C10'—C9'17 (2)
C8—C9—C10—N3176.2 (7)C14'—N3'—C10'—C11'1 (3)
C8—C9—C10—C110.0C13'—N3'—C10'—C11'165.8 (15)
N3—C10—C11—C12176.6 (7)C9'—C10'—C11'—C12'0.0
C9—C10—C11—C120.0N3'—C10'—C11'—C12'177 (2)
C10—C11—C12—C70.0C10'—C11'—C12'—C7'0.0
C8—C7—C12—C110.0C8'—C7'—C12'—C11'0.0
N1—C7—C12—C11179.7 (5)N1'—C7'—C12'—C11'175.9 (17)
 

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