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Anilic acid [or 2,5-bis­(phenyl­amino)terephthalic acid], C20H16N2O4, is an inter­mediate in the industrial synthesis of quinacridone pigments. Single crystals were grown from dimethyl­formamide (DMF), yielding a solvate with two mol­ecules of DMF, C20H16N2O4·2C3H7NO. There are two half-mol­ecules of anilic acid in the asymmetric unit; each molecule is located on a centre of inversion and forms hydrogen bonds to two dimethyl­formamide mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050781/sg2103sup1.cif
Contains datablocks VI, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050781/sg2103VIsup2.hkl
Contains datablock VI

CCDC reference: 633993

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.124
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H22A .. O2A .. 3.14 Ang. PLAT482_ALERT_4_B Small D-H..A Angle Rep for C22A .. O2A .. 89.90 Deg.
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.59 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.52 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C3 H7 N O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 C3 H7 N O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2,5-bis(phenylamino)terephthalic acid dimethylformamide disolvate top
Crystal data top
C20H16N2O4·2C3H7NOZ = 2
Mr = 494.54F(000) = 524
Triclinic, P1Dx = 1.262 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9875 (8) ÅCell parameters from 16656 reflections
b = 10.0220 (8) Åθ = 3.5–25.7°
c = 15.2076 (12) ŵ = 0.09 mm1
α = 83.088 (6)°T = 173 K
β = 74.144 (6)°Block, orange
γ = 82.788 (6)°0.44 × 0.42 × 0.39 mm
V = 1301.92 (19) Å3
Data collection top
Stoe IPDS-II two-circle
diffractometer
4385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 25.6°, θmin = 3.5°
ω scansh = 1010
16656 measured reflectionsk = 1212
4849 independent reflectionsl = 1818
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) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0695P)2 + 0.4015P]
where P = (Fo2 + 2Fc2)/3
4849 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.39 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
O10.21288 (12)0.32944 (10)0.46117 (8)0.0360 (3)
O20.04087 (12)0.35677 (10)0.40802 (8)0.0340 (3)
H20.005 (3)0.447 (3)0.398 (2)0.097 (9)*
C10.07624 (16)0.28306 (13)0.44551 (9)0.0237 (3)
C20.02955 (15)0.13681 (13)0.47047 (8)0.0217 (3)
C30.12054 (15)0.06944 (13)0.43541 (8)0.0214 (3)
C40.14502 (15)0.06669 (13)0.46729 (9)0.0223 (3)
H40.24480.11340.44550.027*
N10.24090 (14)0.13541 (12)0.37432 (8)0.0278 (3)
H10.231 (2)0.2263 (19)0.3724 (12)0.036 (5)*
C110.36583 (15)0.07664 (13)0.30790 (9)0.0235 (3)
C120.35866 (17)0.04159 (14)0.26937 (9)0.0287 (3)
H120.26710.08720.28860.034*
C130.4864 (2)0.09238 (16)0.20254 (10)0.0366 (4)
H130.48190.17380.17760.044*
C140.61978 (19)0.02549 (17)0.17215 (10)0.0391 (4)
H140.70620.06080.12670.047*
C150.62598 (17)0.09357 (17)0.20879 (11)0.0374 (4)
H150.71630.14070.18740.045*
C160.50051 (17)0.14421 (15)0.27665 (10)0.0304 (3)
H160.50630.22500.30190.036*
O210.03795 (14)0.60462 (11)0.37434 (9)0.0434 (3)
C220.17334 (17)0.65025 (14)0.41292 (10)0.0307 (3)
H220.23950.59100.45480.037*
N230.22831 (14)0.77702 (12)0.39803 (9)0.0294 (3)
C240.1318 (2)0.87130 (16)0.33278 (12)0.0391 (4)
H24A0.02400.83070.31590.059*
H24B0.13660.95510.36110.059*
H24C0.17010.89120.27770.059*
C250.3888 (2)0.8254 (2)0.44112 (13)0.0467 (4)
H25A0.44050.75220.48210.070*
H25B0.44360.85550.39360.070*
H25C0.39010.90110.47660.070*
O1A0.23060 (11)0.77121 (10)1.02733 (7)0.0323 (3)
O2A0.02270 (12)0.81938 (10)1.09308 (8)0.0348 (3)
H2A0.010 (3)0.898 (3)1.1075 (16)0.069 (7)*
C1A0.09595 (15)0.74198 (13)1.04741 (9)0.0214 (3)
C2A0.04984 (14)0.61607 (12)1.02220 (8)0.0187 (3)
C3A0.15620 (14)0.53290 (12)0.95900 (8)0.0189 (3)
C4A0.10231 (14)0.41790 (12)0.93865 (9)0.0195 (3)
H4A0.17160.36090.89670.023*
N1A0.31091 (13)0.55997 (12)0.92305 (8)0.0254 (3)
H1A0.337 (2)0.6291 (19)0.9453 (12)0.035 (4)*
C11A0.41135 (15)0.51544 (12)0.83989 (9)0.0231 (3)
C12A0.36141 (19)0.51530 (16)0.76065 (11)0.0352 (4)
H12A0.25540.54030.76180.042*
C13A0.4682 (2)0.4781 (2)0.67980 (11)0.0494 (5)
H13A0.43440.47820.62580.059*
C14A0.6240 (2)0.44094 (19)0.67726 (12)0.0514 (5)
H14A0.69600.41580.62190.062*
C15A0.67247 (19)0.44093 (17)0.75570 (13)0.0439 (4)
H15A0.77860.41630.75420.053*
C16A0.56687 (17)0.47690 (14)0.83744 (11)0.0300 (3)
H16A0.60110.47510.89140.036*
O21A0.04284 (12)1.03843 (10)1.13587 (8)0.0369 (3)
C22A0.17330 (17)1.07365 (13)1.09315 (10)0.0266 (3)
H22A0.23961.01471.05140.032*
N23A0.22559 (14)1.18764 (11)1.10206 (8)0.0243 (3)
C24A0.13197 (19)1.28071 (14)1.16725 (10)0.0313 (3)
H24D0.03781.24021.20320.047*
H24E0.10311.36541.13380.047*
H24F0.19221.29901.20860.047*
C25A0.38127 (17)1.22083 (15)1.05055 (11)0.0324 (3)
H25D0.44411.22551.09340.049*
H25E0.37381.30831.01470.049*
H25F0.43021.15091.00900.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0235 (5)0.0282 (5)0.0488 (6)0.0079 (4)0.0044 (5)0.0030 (5)
O20.0266 (5)0.0197 (5)0.0460 (6)0.0035 (4)0.0019 (5)0.0029 (4)
C10.0233 (7)0.0229 (6)0.0205 (6)0.0045 (5)0.0018 (5)0.0009 (5)
C20.0210 (7)0.0214 (6)0.0196 (6)0.0038 (5)0.0029 (5)0.0013 (5)
C30.0189 (6)0.0235 (6)0.0185 (6)0.0011 (5)0.0006 (5)0.0013 (5)
C40.0174 (6)0.0233 (6)0.0216 (6)0.0048 (5)0.0008 (5)0.0019 (5)
N10.0226 (6)0.0209 (6)0.0307 (6)0.0024 (5)0.0055 (5)0.0004 (5)
C110.0182 (6)0.0250 (6)0.0212 (6)0.0050 (5)0.0009 (5)0.0047 (5)
C120.0251 (7)0.0312 (7)0.0252 (7)0.0007 (6)0.0011 (6)0.0005 (5)
C130.0405 (9)0.0359 (8)0.0261 (7)0.0093 (7)0.0017 (6)0.0035 (6)
C140.0278 (8)0.0495 (9)0.0259 (7)0.0149 (7)0.0052 (6)0.0033 (6)
C150.0189 (7)0.0485 (9)0.0344 (8)0.0002 (6)0.0019 (6)0.0131 (7)
C160.0245 (7)0.0305 (7)0.0304 (7)0.0009 (6)0.0020 (6)0.0060 (6)
O210.0329 (6)0.0274 (5)0.0569 (7)0.0059 (5)0.0035 (5)0.0028 (5)
C220.0266 (7)0.0249 (7)0.0369 (8)0.0017 (6)0.0047 (6)0.0009 (6)
N230.0266 (6)0.0260 (6)0.0351 (7)0.0059 (5)0.0107 (5)0.0039 (5)
C240.0481 (10)0.0273 (7)0.0421 (9)0.0001 (7)0.0171 (8)0.0044 (6)
C250.0318 (9)0.0521 (10)0.0541 (11)0.0185 (8)0.0137 (8)0.0142 (8)
O1A0.0178 (5)0.0304 (5)0.0477 (6)0.0078 (4)0.0017 (4)0.0175 (5)
O2A0.0198 (5)0.0274 (5)0.0540 (7)0.0052 (4)0.0050 (5)0.0220 (5)
C1A0.0181 (6)0.0203 (6)0.0236 (6)0.0019 (5)0.0008 (5)0.0042 (5)
C2A0.0157 (6)0.0168 (6)0.0228 (6)0.0016 (5)0.0039 (5)0.0008 (5)
C3A0.0137 (6)0.0184 (6)0.0227 (6)0.0019 (5)0.0019 (5)0.0006 (5)
C4A0.0141 (6)0.0182 (6)0.0235 (6)0.0007 (5)0.0009 (5)0.0033 (5)
N1A0.0150 (6)0.0260 (6)0.0331 (6)0.0066 (4)0.0033 (5)0.0125 (5)
C11A0.0184 (6)0.0188 (6)0.0285 (7)0.0069 (5)0.0036 (5)0.0053 (5)
C12A0.0314 (8)0.0412 (8)0.0330 (8)0.0150 (7)0.0036 (6)0.0029 (6)
C13A0.0602 (12)0.0597 (11)0.0287 (8)0.0335 (10)0.0024 (8)0.0103 (7)
C14A0.0512 (11)0.0487 (10)0.0422 (10)0.0217 (9)0.0236 (8)0.0232 (8)
C15A0.0255 (8)0.0385 (9)0.0561 (11)0.0030 (7)0.0134 (7)0.0150 (8)
C16A0.0201 (7)0.0280 (7)0.0377 (8)0.0031 (5)0.0020 (6)0.0078 (6)
O21A0.0303 (6)0.0296 (5)0.0468 (6)0.0113 (4)0.0053 (5)0.0150 (5)
C22A0.0268 (7)0.0215 (6)0.0302 (7)0.0032 (5)0.0039 (6)0.0045 (5)
N23A0.0249 (6)0.0211 (5)0.0277 (6)0.0035 (5)0.0081 (5)0.0008 (4)
C24A0.0385 (8)0.0231 (7)0.0336 (8)0.0035 (6)0.0097 (6)0.0064 (6)
C25A0.0265 (8)0.0316 (7)0.0391 (8)0.0087 (6)0.0090 (6)0.0037 (6)
Geometric parameters (Å, º) top
O1—C11.2265 (17)O1A—C1A1.2284 (16)
O2—C11.3208 (17)O2A—C1A1.3185 (16)
O2—H20.93 (3)O2A—H2A0.95 (3)
C1—C21.5057 (17)C1A—C2A1.4985 (17)
C2—C4i1.3974 (18)C2A—C4Aii1.4012 (18)
C2—C31.4229 (18)C2A—C3A1.4223 (17)
C3—N11.3975 (17)C3A—N1A1.3963 (16)
C3—C41.4030 (18)C3A—C4A1.4024 (18)
C4—C2i1.3974 (18)C4A—C2Aii1.4012 (18)
C4—H40.9500C4A—H4A0.9500
N1—C111.4090 (17)N1A—C11A1.4228 (17)
N1—H10.902 (19)N1A—H1A0.889 (19)
C11—C121.399 (2)C11A—C16A1.394 (2)
C11—C161.401 (2)C11A—C12A1.396 (2)
C12—C131.396 (2)C12A—C13A1.396 (2)
C12—H120.9500C12A—H12A0.9500
C13—C141.387 (2)C13A—C14A1.394 (3)
C13—H130.9500C13A—H13A0.9500
C14—C151.390 (3)C14A—C15A1.377 (3)
C14—H140.9500C14A—H14A0.9500
C15—C161.393 (2)C15A—C16A1.398 (2)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
O21—C221.2525 (18)O21A—C22A1.2466 (18)
C22—N231.3206 (19)C22A—N23A1.3233 (17)
C22—H220.9500C22A—H22A0.9500
N23—C251.459 (2)N23A—C24A1.4596 (18)
N23—C241.463 (2)N23A—C25A1.4620 (19)
C24—H24A0.9800C24A—H24D0.9800
C24—H24B0.9800C24A—H24E0.9800
C24—H24C0.9800C24A—H24F0.9800
C25—H25A0.9800C25A—H25D0.9800
C25—H25B0.9800C25A—H25E0.9800
C25—H25C0.9800C25A—H25F0.9800
C1—O2—H2110.9 (18)C1A—O2A—H2A111.1 (15)
O1—C1—O2123.26 (12)O1A—C1A—O2A122.99 (12)
O1—C1—C2121.92 (12)O1A—C1A—C2A123.66 (11)
O2—C1—C2114.80 (11)O2A—C1A—C2A113.34 (11)
C4i—C2—C3119.96 (12)C4Aii—C2A—C3A120.09 (11)
C4i—C2—C1115.61 (11)C4Aii—C2A—C1A118.55 (11)
C3—C2—C1124.43 (12)C3A—C2A—C1A121.36 (11)
N1—C3—C4120.76 (12)N1A—C3A—C4A121.19 (11)
N1—C3—C2122.27 (12)N1A—C3A—C2A121.28 (11)
C4—C3—C2116.94 (12)C4A—C3A—C2A117.41 (11)
C2i—C4—C3123.10 (12)C2Aii—C4A—C3A122.50 (12)
C2i—C4—H4118.5C2Aii—C4A—H4A118.7
C3—C4—H4118.5C3A—C4A—H4A118.7
C3—N1—C11126.78 (11)C3A—N1A—C11A125.41 (11)
C3—N1—H1116.3 (12)C3A—N1A—H1A114.7 (12)
C11—N1—H1116.5 (12)C11A—N1A—H1A117.3 (12)
C12—C11—C16119.07 (13)C16A—C11A—C12A119.55 (13)
C12—C11—N1123.17 (13)C16A—C11A—N1A117.88 (13)
C16—C11—N1117.70 (13)C12A—C11A—N1A122.49 (13)
C13—C12—C11119.86 (14)C13A—C12A—C11A119.54 (16)
C13—C12—H12120.1C13A—C12A—H12A120.2
C11—C12—H12120.1C11A—C12A—H12A120.2
C14—C13—C12120.83 (15)C14A—C13A—C12A120.82 (17)
C14—C13—H13119.6C14A—C13A—H13A119.6
C12—C13—H13119.6C12A—C13A—H13A119.6
C13—C14—C15119.44 (14)C15A—C14A—C13A119.37 (15)
C13—C14—H14120.3C15A—C14A—H14A120.3
C15—C14—H14120.3C13A—C14A—H14A120.3
C14—C15—C16120.37 (15)C14A—C15A—C16A120.59 (16)
C14—C15—H15119.8C14A—C15A—H15A119.7
C16—C15—H15119.8C16A—C15A—H15A119.7
C15—C16—C11120.40 (14)C11A—C16A—C15A120.12 (15)
C15—C16—H16119.8C11A—C16A—H16A119.9
C11—C16—H16119.8C15A—C16A—H16A119.9
O21—C22—N23122.97 (14)O21A—C22A—N23A124.38 (13)
O21—C22—H22118.5O21A—C22A—H22A117.8
N23—C22—H22118.5N23A—C22A—H22A117.8
C22—N23—C25121.54 (14)C22A—N23A—C24A120.72 (12)
C22—N23—C24120.45 (13)C22A—N23A—C25A121.15 (12)
C25—N23—C24117.90 (13)C24A—N23A—C25A118.07 (11)
N23—C24—H24A109.5N23A—C24A—H24D109.5
N23—C24—H24B109.5N23A—C24A—H24E109.5
H24A—C24—H24B109.5H24D—C24A—H24E109.5
N23—C24—H24C109.5N23A—C24A—H24F109.5
H24A—C24—H24C109.5H24D—C24A—H24F109.5
H24B—C24—H24C109.5H24E—C24A—H24F109.5
N23—C25—H25A109.5N23A—C25A—H25D109.5
N23—C25—H25B109.5N23A—C25A—H25E109.5
H25A—C25—H25B109.5H25D—C25A—H25E109.5
N23—C25—H25C109.5N23A—C25A—H25F109.5
H25A—C25—H25C109.5H25D—C25A—H25F109.5
H25B—C25—H25C109.5H25E—C25A—H25F109.5
O1—C1—C2—C4i16.08 (19)O1A—C1A—C2A—C4Aii169.62 (13)
O2—C1—C2—C4i162.28 (12)O2A—C1A—C2A—C4Aii10.74 (17)
O1—C1—C2—C3164.14 (13)O1A—C1A—C2A—C3A11.3 (2)
O2—C1—C2—C317.50 (19)O2A—C1A—C2A—C3A168.36 (12)
C4i—C2—C3—N1178.85 (12)C4Aii—C2A—C3A—N1A176.25 (12)
C1—C2—C3—N10.9 (2)C1A—C2A—C3A—N1A4.67 (19)
C4i—C2—C3—C40.9 (2)C4Aii—C2A—C3A—C4A0.2 (2)
C1—C2—C3—C4178.88 (12)C1A—C2A—C3A—C4A179.24 (11)
N1—C3—C4—C2i178.91 (12)N1A—C3A—C4A—C2Aii176.25 (12)
C2—C3—C4—C2i0.9 (2)C2A—C3A—C4A—C2Aii0.2 (2)
C4—C3—N1—C1130.1 (2)C4A—C3A—N1A—C11A26.3 (2)
C2—C3—N1—C11152.02 (13)C2A—C3A—N1A—C11A157.76 (13)
C3—N1—C11—C1225.2 (2)C3A—N1A—C11A—C16A142.53 (13)
C3—N1—C11—C16157.69 (13)C3A—N1A—C11A—C12A40.6 (2)
C16—C11—C12—C131.7 (2)C16A—C11A—C12A—C13A0.8 (2)
N1—C11—C12—C13178.77 (13)N1A—C11A—C12A—C13A176.08 (14)
C11—C12—C13—C141.4 (2)C11A—C12A—C13A—C14A0.1 (3)
C12—C13—C14—C150.0 (2)C12A—C13A—C14A—C15A0.0 (3)
C13—C14—C15—C161.2 (2)C13A—C14A—C15A—C16A0.4 (3)
C14—C15—C16—C110.8 (2)C12A—C11A—C16A—C15A1.2 (2)
C12—C11—C16—C150.6 (2)N1A—C11A—C16A—C15A175.76 (13)
N1—C11—C16—C15177.83 (13)C14A—C15A—C16A—C11A1.1 (2)
O21—C22—N23—C25177.31 (15)O21A—C22A—N23A—C24A2.1 (2)
O21—C22—N23—C241.2 (2)O21A—C22A—N23A—C25A178.99 (14)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O210.93 (3)1.60 (3)2.5268 (14)174 (3)
C22—H22···O10.952.593.2524 (18)127
N1—H1···O20.902 (19)2.006 (18)2.6805 (15)130.5 (16)
O2A—H2A···O21A0.95 (3)1.60 (3)2.5432 (14)173 (2)
C22A—H22A···O2A0.953.143.2750 (17)90
N1A—H1A···O1A0.889 (19)1.984 (19)2.7049 (15)137.2 (16)
C4—H4···O1i0.952.442.7856 (16)101
C4A—H4A···O2Aii0.952.352.7003 (16)102
C14—H14···O2Aiii0.952.523.3574 (18)146
C14A—H14A···O1iv0.952.583.469 (2)157
C24—H24A···O210.982.342.7517 (19)105
C24A—H24D···O21A0.982.362.7824 (17)105
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+2; (iii) x+1, y1, z1; (iv) x+1, y, z.
 

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