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The structure of the title compound, C22H18N6O4, (I), comprises two unique mol­ecules that separately form hydrogen-bonded polymer chains via N-H...N interactions. Molecular independence arises due to a difference in the dihedral angles between the linked rings, i.e. 52.19 (4) and 46.17 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100014189/qa0430sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100014189/qa0430Isup2.hkl
Contains datablock I

CCDC reference: 153958

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997 and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

'4-Anilino-3-nitropyridine' top
Crystal data top
C11H9N3O2Dx = 1.462 Mg m3
Mr = 215.21Melting point: 387 - 388 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.9036 (2) ÅCell parameters from 9171 reflections
b = 19.9452 (4) Åθ = 2.9–27.5°
c = 13.6660 (3) ŵ = 0.11 mm1
β = 133.561 (1)°T = 150 K
V = 1956.12 (7) Å3Block, yellow
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 896
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
4333 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode3232 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
φ and ω scansh = 1212
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
k = 2522
Tmin = 0.969, Tmax = 0.979l = 1716
18006 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0691P)2 + 0.1181P]
where P = (Fo2 + 2Fc2)/3
4333 reflections(Δ/σ)max = 0.001
297 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.0603 (0.0046) x + 0.7416 (0.0124) y + 13.5866 (0.0009) z = 0.2500 (0.0030)

* -0.0019 (0.0010) N1A * -0.0013 (0.0010) C2A * 0.0003 (0.0010) C3A * 0.0035 (0.0010) C4A * -0.0069 (0.0010) C5A * 0.0063 (0.0011) C6A

Rms deviation of fitted atoms = 0.0042

9.6979 (0.0010) x + 4.0082 (0.0100) y - 9.4896 (0.0053) z = 2.1318 (0.0012)

Angle to previous plane (with approximate e.s.d.) = 52.19 (0.04)

* -0.0086 (0.0009) C7A * 0.0016 (0.0009) C8A * 0.0058 (0.0009) C9A * -0.0062 (0.0010) C10A * -0.0008 (0.0010) C11A * 0.0082 (0.0009) C12A

Rms deviation of fitted atoms = 0.0060

- 7.4134 (0.0036) x + 3.2245 (0.0121) y + 13.4178 (0.0017) z = 5.2551 (0.0086)

Angle to previous plane (with approximate e.s.d.) = 44.12 (0.04)

* -0.0115 (0.0010) N1B * -0.0048 (0.0010) C2B * 0.0194 (0.0010) C3B * -0.0185 (0.0009) C4B * 0.0033 (0.0010) C5B * 0.0121 (0.0010) C6B

Rms deviation of fitted atoms = 0.0131

1.5586 (0.0064) x + 5.3431 (0.0119) y - 10.8950 (0.0053) z = 0.3226 (0.0072)

Angle to previous plane (with approximate e.s.d.) = 46.71 (0.05)

* -0.0052 (0.0010) C7B * 0.0029 (0.0010) C8B * 0.0014 (0.0011) C9B * -0.0033 (0.0011) C10B * 0.0008 (0.0011) C11B * 0.0034 (0.0011) C12B

Rms deviation of fitted atoms = 0.0032

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.27770 (15)0.26138 (5)0.11988 (14)0.0318 (3)
C2A0.13396 (18)0.30229 (7)0.05795 (15)0.0287 (3)
H2A0.15810.34910.07130.036*
C3A0.05052 (18)0.28132 (6)0.02560 (15)0.0246 (3)
N31A0.18796 (15)0.33360 (5)0.08462 (13)0.0280 (3)
O31A0.13772 (15)0.39193 (5)0.05191 (13)0.0491 (3)
O32A0.35416 (13)0.31784 (5)0.16729 (12)0.0377 (3)
C4A0.09858 (18)0.21252 (6)0.05103 (14)0.0241 (3)
C5A0.05793 (18)0.16999 (6)0.01723 (16)0.0276 (3)
H5A0.04060.12280.00810.034*
C6A0.23285 (19)0.19553 (6)0.09567 (16)0.0300 (3)
H6A0.33200.16450.13700.037*
N41A0.27452 (16)0.18850 (5)0.13343 (13)0.0271 (3)
H41A0.368 (3)0.2173 (9)0.183 (2)0.048 (5)*
C7A0.32538 (18)0.11938 (6)0.15920 (15)0.0250 (3)
C8A0.46514 (17)0.09882 (6)0.29228 (15)0.0277 (3)
H8A0.52210.13040.36330.035*
C9A0.52205 (19)0.03260 (6)0.32202 (16)0.0318 (3)
H9A0.61830.01880.41340.040*
C10A0.4393 (2)0.01360 (7)0.21916 (17)0.0338 (4)
H10A0.47700.05920.23970.042*
C11A0.3014 (2)0.00683 (6)0.08639 (17)0.0336 (3)
H11A0.24520.02490.01570.042*
C12A0.24441 (18)0.07330 (6)0.05522 (16)0.0296 (3)
H12A0.15090.08720.03630.037*
N1B0.74445 (15)0.75523 (5)0.62062 (14)0.0314 (3)
C2B0.60329 (19)0.79626 (6)0.53326 (16)0.0279 (3)
H2B0.63080.84230.53640.035*
C3B0.41683 (18)0.77663 (6)0.43677 (15)0.0248 (3)
N31B0.28238 (15)0.82911 (5)0.35577 (13)0.0284 (3)
O31B0.33667 (14)0.88592 (5)0.36233 (13)0.0423 (3)
O32B0.11555 (13)0.81565 (4)0.28263 (12)0.0386 (3)
C4B0.36574 (18)0.70840 (6)0.42211 (14)0.0246 (3)
C5B0.51869 (19)0.66589 (6)0.51846 (16)0.0283 (3)
H5B0.49780.61940.51870.035*
C6B0.69577 (19)0.69048 (7)0.61104 (16)0.0307 (3)
H6B0.79290.65970.67390.038*
N41B0.18844 (16)0.68528 (5)0.32711 (13)0.0262 (3)
H41B0.101 (2)0.7142 (8)0.2864 (19)0.036 (4)*
C7B0.13384 (18)0.61698 (6)0.29260 (15)0.0250 (3)
C8B0.02872 (17)0.59715 (6)0.25887 (15)0.0264 (3)
H8B0.09600.62840.26400.033*
C9B0.09257 (18)0.53186 (6)0.21786 (16)0.0305 (3)
H9B0.20330.51850.19520.038*
C10B0.00433 (19)0.48623 (7)0.20977 (16)0.0325 (3)
H10B0.03910.44140.18210.041*
C11B0.1648 (2)0.50607 (6)0.24207 (16)0.0334 (3)
H11B0.23100.47470.23610.042*
C12B0.23022 (19)0.57110 (6)0.28309 (16)0.0296 (3)
H12B0.34030.58430.30460.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0251 (6)0.0324 (6)0.0336 (8)0.0019 (4)0.0185 (6)0.0034 (5)
C2A0.0275 (7)0.0268 (7)0.0299 (9)0.0041 (5)0.0190 (7)0.0030 (5)
C3A0.0247 (7)0.0256 (7)0.0228 (8)0.0005 (5)0.0161 (6)0.0012 (5)
N31A0.0266 (6)0.0255 (6)0.0263 (7)0.0010 (4)0.0161 (6)0.0008 (5)
O31A0.0353 (6)0.0238 (5)0.0565 (9)0.0018 (4)0.0196 (6)0.0012 (5)
O32A0.0219 (5)0.0314 (5)0.0411 (7)0.0005 (4)0.0146 (5)0.0008 (4)
C4A0.0236 (6)0.0275 (7)0.0217 (8)0.0027 (5)0.0158 (6)0.0010 (5)
C5A0.0255 (7)0.0269 (7)0.0299 (9)0.0007 (5)0.0189 (7)0.0018 (6)
C6A0.0236 (7)0.0313 (7)0.0308 (9)0.0008 (5)0.0172 (7)0.0019 (6)
N41A0.0211 (6)0.0246 (6)0.0288 (7)0.0005 (4)0.0146 (6)0.0013 (5)
C7A0.0213 (6)0.0244 (6)0.0300 (9)0.0005 (5)0.0180 (6)0.0009 (5)
C8A0.0237 (7)0.0317 (7)0.0272 (9)0.0015 (5)0.0173 (7)0.0019 (6)
C9A0.0255 (7)0.0333 (7)0.0328 (9)0.0034 (5)0.0187 (7)0.0075 (6)
C10A0.0298 (7)0.0246 (7)0.0449 (11)0.0020 (5)0.0249 (8)0.0035 (6)
C11A0.0318 (7)0.0274 (7)0.0400 (10)0.0033 (5)0.0242 (7)0.0064 (6)
C12A0.0254 (7)0.0316 (7)0.0272 (9)0.0008 (5)0.0164 (7)0.0005 (6)
N1B0.0243 (6)0.0310 (6)0.0319 (8)0.0008 (4)0.0167 (6)0.0049 (5)
C2B0.0252 (7)0.0276 (7)0.0312 (9)0.0025 (5)0.0195 (7)0.0044 (6)
C3B0.0236 (7)0.0264 (7)0.0245 (8)0.0009 (5)0.0165 (6)0.0009 (5)
N31B0.0249 (6)0.0267 (6)0.0312 (8)0.0010 (4)0.0184 (6)0.0015 (5)
O31B0.0335 (6)0.0262 (5)0.0546 (9)0.0022 (4)0.0255 (6)0.0024 (5)
O32B0.0214 (5)0.0325 (5)0.0470 (8)0.0003 (4)0.0178 (5)0.0015 (5)
C4B0.0234 (6)0.0288 (7)0.0240 (8)0.0022 (5)0.0172 (6)0.0024 (5)
C5B0.0274 (7)0.0260 (7)0.0285 (9)0.0001 (5)0.0181 (7)0.0002 (5)
C6B0.0257 (7)0.0320 (7)0.0282 (9)0.0024 (5)0.0162 (7)0.0007 (6)
N41B0.0208 (6)0.0243 (6)0.0285 (7)0.0011 (4)0.0151 (5)0.0009 (5)
C7B0.0226 (6)0.0258 (6)0.0212 (8)0.0018 (5)0.0130 (6)0.0003 (5)
C8B0.0216 (6)0.0305 (7)0.0225 (8)0.0015 (5)0.0134 (6)0.0021 (5)
C9B0.0238 (7)0.0315 (7)0.0301 (9)0.0044 (5)0.0162 (7)0.0000 (6)
C10B0.0293 (7)0.0263 (7)0.0344 (10)0.0037 (5)0.0190 (7)0.0028 (6)
C11B0.0315 (8)0.0303 (7)0.0379 (10)0.0007 (5)0.0238 (8)0.0043 (6)
C12B0.0258 (7)0.0323 (7)0.0312 (9)0.0030 (5)0.0198 (7)0.0031 (6)
Geometric parameters (Å, º) top
N1A—C2A1.3222 (17)N1B—C2B1.3225 (18)
N1A—C6A1.3524 (16)N1B—C6B1.3529 (16)
C2A—C3A1.3933 (18)C2B—C3B1.3950 (18)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.4150 (17)C3B—C4B1.4173 (18)
C3A—N31A1.4413 (16)C3B—N31B1.4361 (17)
N31A—O31A1.2224 (14)N31B—O31B1.2307 (13)
N31A—O32A1.2335 (14)N31B—O32B1.2349 (14)
C4A—N41A1.3526 (16)C4B—N41B1.3563 (17)
C4A—C5A1.4141 (18)C4B—C5B1.4136 (19)
C5A—C6A1.3602 (19)C5B—C6B1.3634 (19)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
N41A—C7A1.4260 (16)N41B—C7B1.4209 (16)
N41A—H41A0.882 (19)N41B—H41B0.851 (17)
C7A—C8A1.386 (2)C7B—C12B1.3915 (18)
C7A—C12A1.392 (2)C7B—C8B1.3922 (18)
C8A—C9A1.3825 (18)C8B—C9B1.3860 (18)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.382 (2)C9B—C10B1.3812 (19)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.381 (2)C10B—C11B1.3818 (19)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.3880 (18)C11B—C12B1.3841 (18)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C2A—N1A—C6A114.55 (11)C2B—N1B—C6B114.76 (11)
N1A—C2A—C3A124.37 (12)N1B—C2B—C3B124.53 (12)
N1A—C2A—H2A117.8N1B—C2B—H2B117.7
C3A—C2A—H2A117.8C3B—C2B—H2B117.7
C2A—C3A—C4A121.44 (12)C2B—C3B—C4B120.95 (12)
C2A—C3A—N31A116.15 (11)C2B—C3B—N31B116.38 (11)
C4A—C3A—N31A122.41 (11)C4B—C3B—N31B122.67 (11)
O31A—N31A—O32A121.84 (11)O31B—N31B—O32B122.20 (11)
O31A—N31A—C3A119.63 (11)O31B—N31B—C3B119.24 (11)
O32A—N31A—C3A118.53 (10)O32B—N31B—C3B118.56 (10)
N41A—C4A—C5A122.29 (11)N41B—C4B—C5B122.49 (12)
N41A—C4A—C3A124.78 (12)N41B—C4B—C3B124.22 (12)
C5A—C4A—C3A112.92 (11)C5B—C4B—C3B113.28 (12)
C6A—C5A—C4A121.13 (12)C6B—C5B—C4B121.06 (12)
C6A—C5A—H5A119.4C6B—C5B—H5B119.5
C4A—C5A—H5A119.4C4B—C5B—H5B119.5
N1A—C6A—C5A125.57 (12)N1B—C6B—C5B125.31 (13)
N1A—C6A—H6A117.2N1B—C6B—H6B117.3
C5A—C6A—H6A117.2C5B—C6B—H6B117.3
C4A—N41A—C7A125.53 (11)C4B—N41B—C7B126.10 (11)
C4A—N41A—H41A118.3 (11)C4B—N41B—H41B117.1 (11)
C7A—N41A—H41A115.7 (11)C7B—N41B—H41B116.8 (11)
C8A—C7A—C12A119.73 (12)C12B—C7B—C8B119.56 (11)
C8A—C7A—N41A118.26 (12)C12B—C7B—N41B122.20 (11)
C12A—C7A—N41A121.97 (13)C8B—C7B—N41B118.10 (11)
C9A—C8A—C7A120.30 (13)C9B—C8B—C7B120.13 (12)
C9A—C8A—H8A119.8C9B—C8B—H8B119.9
C7A—C8A—H8A119.8C7B—C8B—H8B119.9
C10A—C9A—C8A120.14 (14)C10B—C9B—C8B120.19 (12)
C10A—C9A—H9A119.9C10B—C9B—H9B119.9
C8A—C9A—H9A119.9C8B—C9B—H9B119.9
C11A—C10A—C9A119.75 (12)C9B—C10B—C11B119.68 (12)
C11A—C10A—H10A120.1C9B—C10B—H10B120.2
C9A—C10A—H10A120.1C11B—C10B—H10B120.2
C10A—C11A—C12A120.64 (14)C10B—C11B—C12B120.81 (12)
C10A—C11A—H11A119.7C10B—C11B—H11B119.6
C12A—C11A—H11A119.7C12B—C11B—H11B119.6
C11A—C12A—C7A119.42 (14)C11B—C12B—C7B119.62 (12)
C11A—C12A—H12A120.3C11B—C12B—H12B120.2
C7A—C12A—H12A120.3C7B—C12B—H12B120.2
C6A—N1A—C2A—C3A0.3 (2)C6B—N1B—C2B—C3B0.2 (2)
N1A—C2A—C3A—C4A0.1 (2)N1B—C2B—C3B—C4B2.7 (2)
N1A—C2A—C3A—N31A179.68 (14)N1B—C2B—C3B—N31B176.63 (14)
C2A—C3A—N31A—O31A5.5 (2)C2B—C3B—N31B—O31B9.3 (2)
C4A—C3A—N31A—O31A174.95 (14)C4B—C3B—N31B—O31B171.39 (13)
C2A—C3A—N31A—O32A174.56 (13)C2B—C3B—N31B—O32B170.01 (13)
C4A—C3A—N31A—O32A5.0 (2)C4B—C3B—N31B—O32B9.3 (2)
C2A—C3A—C4A—N41A178.26 (14)C2B—C3B—C4B—N41B177.18 (13)
N31A—C3A—C4A—N41A1.3 (2)N31B—C3B—C4B—N41B3.5 (2)
C2A—C3A—C4A—C5A0.5 (2)C2B—C3B—C4B—C5B3.70 (19)
N31A—C3A—C4A—C5A179.93 (13)N31B—C3B—C4B—C5B175.61 (13)
N41A—C4A—C5A—C6A177.58 (14)N41B—C4B—C5B—C6B178.72 (14)
C3A—C4A—C5A—C6A1.2 (2)C3B—C4B—C5B—C6B2.1 (2)
C2A—N1A—C6A—C5A1.1 (2)C2B—N1B—C6B—C5B1.9 (2)
C4A—C5A—C6A—N1A1.7 (2)C4B—C5B—C6B—N1B0.7 (2)
C5A—C4A—N41A—C7A2.0 (2)C5B—C4B—N41B—C7B13.0 (2)
C3A—C4A—N41A—C7A179.35 (13)C3B—C4B—N41B—C7B167.91 (13)
C4A—N41A—C7A—C8A131.04 (14)C4B—N41B—C7B—C12B40.5 (2)
C4A—N41A—C7A—C12A51.57 (19)C4B—N41B—C7B—C8B143.77 (14)
C12A—C7A—C8A—C9A1.08 (19)C12B—C7B—C8B—C9B0.9 (2)
N41A—C7A—C8A—C9A178.52 (11)N41B—C7B—C8B—C9B176.70 (13)
C7A—C8A—C9A—C10A0.29 (19)C7B—C8B—C9B—C10B0.2 (2)
C8A—C9A—C10A—C11A1.0 (2)C8B—C9B—C10B—C11B0.3 (2)
C9A—C10A—C11A—C12A0.4 (2)C9B—C10B—C11B—C12B0.3 (2)
C10A—C11A—C12A—C7A1.0 (2)C10B—C11B—C12B—C7B0.3 (2)
C8A—C7A—C12A—C11A1.69 (19)C8B—C7B—C12B—C11B0.9 (2)
N41A—C7A—C12A—C11A179.04 (12)N41B—C7B—C12B—C11B176.57 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41A—H41A···O32A0.882 (19)2.012 (17)2.6434 (14)127.5 (15)
N41A—H41A···N1Ai0.882 (19)2.595 (19)3.3802 (16)148.8 (15)
N41B—H41B···O32B0.851 (17)2.031 (16)2.6547 (14)129.4 (14)
N41B—H41B···N1Bii0.851 (17)2.638 (17)3.4064 (16)150.7 (13)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y+3/2, z1/2.
 

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