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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
CCDC reference: 633993
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C20H16N2O4·2C3H7NO | Z = 2 |
Mr = 494.54 | F(000) = 524 |
Triclinic, P1 | Dx = 1.262 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9875 (8) Å | Cell parameters from 16656 reflections |
b = 10.0220 (8) Å | θ = 3.5–25.7° |
c = 15.2076 (12) Å | µ = 0.09 mm−1 |
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 tube | Rint = 0.062 |
Graphite monochromator | θmax = 25.6°, θmin = 3.5° |
ω scans | h = −10→10 |
16656 measured reflections | k = −12→12 |
4849 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H 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 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | −0.21288 (12) | 0.32944 (10) | 0.46117 (8) | 0.0360 (3) | |
O2 | 0.04087 (12) | 0.35677 (10) | 0.40802 (8) | 0.0340 (3) | |
H2 | 0.005 (3) | 0.447 (3) | 0.398 (2) | 0.097 (9)* | |
C1 | −0.07624 (16) | 0.28306 (13) | 0.44551 (9) | 0.0237 (3) | |
C2 | −0.02955 (15) | 0.13681 (13) | 0.47047 (8) | 0.0217 (3) | |
C3 | 0.12054 (15) | 0.06944 (13) | 0.43541 (8) | 0.0214 (3) | |
C4 | 0.14502 (15) | −0.06669 (13) | 0.46729 (9) | 0.0223 (3) | |
H4 | 0.2448 | −0.1134 | 0.4455 | 0.027* | |
N1 | 0.24090 (14) | 0.13541 (12) | 0.37432 (8) | 0.0278 (3) | |
H1 | 0.231 (2) | 0.2263 (19) | 0.3724 (12) | 0.036 (5)* | |
C11 | 0.36583 (15) | 0.07664 (13) | 0.30790 (9) | 0.0235 (3) | |
C12 | 0.35866 (17) | −0.04159 (14) | 0.26937 (9) | 0.0287 (3) | |
H12 | 0.2671 | −0.0872 | 0.2886 | 0.034* | |
C13 | 0.4864 (2) | −0.09238 (16) | 0.20254 (10) | 0.0366 (4) | |
H13 | 0.4819 | −0.1738 | 0.1776 | 0.044* | |
C14 | 0.61978 (19) | −0.02549 (17) | 0.17215 (10) | 0.0391 (4) | |
H14 | 0.7062 | −0.0608 | 0.1267 | 0.047* | |
C15 | 0.62598 (17) | 0.09357 (17) | 0.20879 (11) | 0.0374 (4) | |
H15 | 0.7163 | 0.1407 | 0.1874 | 0.045* | |
C16 | 0.50051 (17) | 0.14421 (15) | 0.27665 (10) | 0.0304 (3) | |
H16 | 0.5063 | 0.2250 | 0.3019 | 0.036* | |
O21 | −0.03795 (14) | 0.60462 (11) | 0.37434 (9) | 0.0434 (3) | |
C22 | −0.17334 (17) | 0.65025 (14) | 0.41292 (10) | 0.0307 (3) | |
H22 | −0.2395 | 0.5910 | 0.4548 | 0.037* | |
N23 | −0.22831 (14) | 0.77702 (12) | 0.39803 (9) | 0.0294 (3) | |
C24 | −0.1318 (2) | 0.87130 (16) | 0.33278 (12) | 0.0391 (4) | |
H24A | −0.0240 | 0.8307 | 0.3159 | 0.059* | |
H24B | −0.1366 | 0.9551 | 0.3611 | 0.059* | |
H24C | −0.1701 | 0.8912 | 0.2777 | 0.059* | |
C25 | −0.3888 (2) | 0.8254 (2) | 0.44112 (13) | 0.0467 (4) | |
H25A | −0.4405 | 0.7522 | 0.4821 | 0.070* | |
H25B | −0.4436 | 0.8555 | 0.3936 | 0.070* | |
H25C | −0.3901 | 0.9011 | 0.4766 | 0.070* | |
O1A | 0.23060 (11) | 0.77121 (10) | 1.02733 (7) | 0.0323 (3) | |
O2A | −0.02270 (12) | 0.81938 (10) | 1.09308 (8) | 0.0348 (3) | |
H2A | 0.010 (3) | 0.898 (3) | 1.1075 (16) | 0.069 (7)* | |
C1A | 0.09595 (15) | 0.74198 (13) | 1.04741 (9) | 0.0214 (3) | |
C2A | 0.04984 (14) | 0.61607 (12) | 1.02220 (8) | 0.0187 (3) | |
C3A | 0.15620 (14) | 0.53290 (12) | 0.95900 (8) | 0.0189 (3) | |
C4A | 0.10231 (14) | 0.41790 (12) | 0.93865 (9) | 0.0195 (3) | |
H4A | 0.1716 | 0.3609 | 0.8967 | 0.023* | |
N1A | 0.31091 (13) | 0.55997 (12) | 0.92305 (8) | 0.0254 (3) | |
H1A | 0.337 (2) | 0.6291 (19) | 0.9453 (12) | 0.035 (4)* | |
C11A | 0.41135 (15) | 0.51544 (12) | 0.83989 (9) | 0.0231 (3) | |
C12A | 0.36141 (19) | 0.51530 (16) | 0.76065 (11) | 0.0352 (4) | |
H12A | 0.2554 | 0.5403 | 0.7618 | 0.042* | |
C13A | 0.4682 (2) | 0.4781 (2) | 0.67980 (11) | 0.0494 (5) | |
H13A | 0.4344 | 0.4782 | 0.6258 | 0.059* | |
C14A | 0.6240 (2) | 0.44094 (19) | 0.67726 (12) | 0.0514 (5) | |
H14A | 0.6960 | 0.4158 | 0.6219 | 0.062* | |
C15A | 0.67247 (19) | 0.44093 (17) | 0.75570 (13) | 0.0439 (4) | |
H15A | 0.7786 | 0.4163 | 0.7542 | 0.053* | |
C16A | 0.56687 (17) | 0.47690 (14) | 0.83744 (11) | 0.0300 (3) | |
H16A | 0.6011 | 0.4751 | 0.8914 | 0.036* | |
O21A | 0.04284 (12) | 1.03843 (10) | 1.13587 (8) | 0.0369 (3) | |
C22A | 0.17330 (17) | 1.07365 (13) | 1.09315 (10) | 0.0266 (3) | |
H22A | 0.2396 | 1.0147 | 1.0514 | 0.032* | |
N23A | 0.22559 (14) | 1.18764 (11) | 1.10206 (8) | 0.0243 (3) | |
C24A | 0.13197 (19) | 1.28071 (14) | 1.16725 (10) | 0.0313 (3) | |
H24D | 0.0378 | 1.2402 | 1.2032 | 0.047* | |
H24E | 0.1031 | 1.3654 | 1.1338 | 0.047* | |
H24F | 0.1922 | 1.2990 | 1.2086 | 0.047* | |
C25A | 0.38127 (17) | 1.22083 (15) | 1.05055 (11) | 0.0324 (3) | |
H25D | 0.4441 | 1.2255 | 1.0934 | 0.049* | |
H25E | 0.3738 | 1.3083 | 1.0147 | 0.049* | |
H25F | 0.4302 | 1.1509 | 1.0090 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0235 (5) | 0.0282 (5) | 0.0488 (6) | 0.0079 (4) | −0.0044 (5) | 0.0030 (5) |
O2 | 0.0266 (5) | 0.0197 (5) | 0.0460 (6) | 0.0035 (4) | 0.0019 (5) | 0.0029 (4) |
C1 | 0.0233 (7) | 0.0229 (6) | 0.0205 (6) | 0.0045 (5) | −0.0018 (5) | −0.0009 (5) |
C2 | 0.0210 (7) | 0.0214 (6) | 0.0196 (6) | 0.0038 (5) | −0.0029 (5) | −0.0013 (5) |
C3 | 0.0189 (6) | 0.0235 (6) | 0.0185 (6) | 0.0011 (5) | −0.0006 (5) | −0.0013 (5) |
C4 | 0.0174 (6) | 0.0233 (6) | 0.0216 (6) | 0.0048 (5) | −0.0008 (5) | −0.0019 (5) |
N1 | 0.0226 (6) | 0.0209 (6) | 0.0307 (6) | 0.0024 (5) | 0.0055 (5) | 0.0004 (5) |
C11 | 0.0182 (6) | 0.0250 (6) | 0.0212 (6) | 0.0050 (5) | −0.0009 (5) | 0.0047 (5) |
C12 | 0.0251 (7) | 0.0312 (7) | 0.0252 (7) | 0.0007 (6) | −0.0011 (6) | −0.0005 (5) |
C13 | 0.0405 (9) | 0.0359 (8) | 0.0261 (7) | 0.0093 (7) | −0.0017 (6) | −0.0035 (6) |
C14 | 0.0278 (8) | 0.0495 (9) | 0.0259 (7) | 0.0149 (7) | 0.0052 (6) | 0.0033 (6) |
C15 | 0.0189 (7) | 0.0485 (9) | 0.0344 (8) | −0.0002 (6) | 0.0019 (6) | 0.0131 (7) |
C16 | 0.0245 (7) | 0.0305 (7) | 0.0304 (7) | −0.0009 (6) | −0.0020 (6) | 0.0060 (6) |
O21 | 0.0329 (6) | 0.0274 (5) | 0.0569 (7) | 0.0059 (5) | 0.0035 (5) | 0.0028 (5) |
C22 | 0.0266 (7) | 0.0249 (7) | 0.0369 (8) | 0.0017 (6) | −0.0047 (6) | −0.0009 (6) |
N23 | 0.0266 (6) | 0.0260 (6) | 0.0351 (7) | 0.0059 (5) | −0.0107 (5) | −0.0039 (5) |
C24 | 0.0481 (10) | 0.0273 (7) | 0.0421 (9) | −0.0001 (7) | −0.0171 (8) | 0.0044 (6) |
C25 | 0.0318 (9) | 0.0521 (10) | 0.0541 (11) | 0.0185 (8) | −0.0137 (8) | −0.0142 (8) |
O1A | 0.0178 (5) | 0.0304 (5) | 0.0477 (6) | −0.0078 (4) | 0.0017 (4) | −0.0175 (5) |
O2A | 0.0198 (5) | 0.0274 (5) | 0.0540 (7) | −0.0052 (4) | 0.0050 (5) | −0.0220 (5) |
C1A | 0.0181 (6) | 0.0203 (6) | 0.0236 (6) | −0.0019 (5) | −0.0008 (5) | −0.0042 (5) |
C2A | 0.0157 (6) | 0.0168 (6) | 0.0228 (6) | −0.0016 (5) | −0.0039 (5) | −0.0008 (5) |
C3A | 0.0137 (6) | 0.0184 (6) | 0.0227 (6) | −0.0019 (5) | −0.0019 (5) | −0.0006 (5) |
C4A | 0.0141 (6) | 0.0182 (6) | 0.0235 (6) | 0.0007 (5) | −0.0009 (5) | −0.0033 (5) |
N1A | 0.0150 (6) | 0.0260 (6) | 0.0331 (6) | −0.0066 (4) | 0.0033 (5) | −0.0125 (5) |
C11A | 0.0184 (6) | 0.0188 (6) | 0.0285 (7) | −0.0069 (5) | 0.0036 (5) | −0.0053 (5) |
C12A | 0.0314 (8) | 0.0412 (8) | 0.0330 (8) | −0.0150 (7) | −0.0036 (6) | −0.0029 (6) |
C13A | 0.0602 (12) | 0.0597 (11) | 0.0287 (8) | −0.0335 (10) | 0.0024 (8) | −0.0103 (7) |
C14A | 0.0512 (11) | 0.0487 (10) | 0.0422 (10) | −0.0217 (9) | 0.0236 (8) | −0.0232 (8) |
C15A | 0.0255 (8) | 0.0385 (9) | 0.0561 (11) | −0.0030 (7) | 0.0134 (7) | −0.0150 (8) |
C16A | 0.0201 (7) | 0.0280 (7) | 0.0377 (8) | −0.0031 (5) | 0.0020 (6) | −0.0078 (6) |
O21A | 0.0303 (6) | 0.0296 (5) | 0.0468 (6) | −0.0113 (4) | 0.0053 (5) | −0.0150 (5) |
C22A | 0.0268 (7) | 0.0215 (6) | 0.0302 (7) | −0.0032 (5) | −0.0039 (6) | −0.0045 (5) |
N23A | 0.0249 (6) | 0.0211 (5) | 0.0277 (6) | −0.0035 (5) | −0.0081 (5) | −0.0008 (4) |
C24A | 0.0385 (8) | 0.0231 (7) | 0.0336 (8) | −0.0035 (6) | −0.0097 (6) | −0.0064 (6) |
C25A | 0.0265 (8) | 0.0316 (7) | 0.0391 (8) | −0.0087 (6) | −0.0090 (6) | 0.0037 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2265 (17) | O1A—C1A | 1.2284 (16) |
O2—C1 | 1.3208 (17) | O2A—C1A | 1.3185 (16) |
O2—H2 | 0.93 (3) | O2A—H2A | 0.95 (3) |
C1—C2 | 1.5057 (17) | C1A—C2A | 1.4985 (17) |
C2—C4i | 1.3974 (18) | C2A—C4Aii | 1.4012 (18) |
C2—C3 | 1.4229 (18) | C2A—C3A | 1.4223 (17) |
C3—N1 | 1.3975 (17) | C3A—N1A | 1.3963 (16) |
C3—C4 | 1.4030 (18) | C3A—C4A | 1.4024 (18) |
C4—C2i | 1.3974 (18) | C4A—C2Aii | 1.4012 (18) |
C4—H4 | 0.9500 | C4A—H4A | 0.9500 |
N1—C11 | 1.4090 (17) | N1A—C11A | 1.4228 (17) |
N1—H1 | 0.902 (19) | N1A—H1A | 0.889 (19) |
C11—C12 | 1.399 (2) | C11A—C16A | 1.394 (2) |
C11—C16 | 1.401 (2) | C11A—C12A | 1.396 (2) |
C12—C13 | 1.396 (2) | C12A—C13A | 1.396 (2) |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C13—C14 | 1.387 (2) | C13A—C14A | 1.394 (3) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C14—C15 | 1.390 (3) | C14A—C15A | 1.377 (3) |
C14—H14 | 0.9500 | C14A—H14A | 0.9500 |
C15—C16 | 1.393 (2) | C15A—C16A | 1.398 (2) |
C15—H15 | 0.9500 | C15A—H15A | 0.9500 |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
O21—C22 | 1.2525 (18) | O21A—C22A | 1.2466 (18) |
C22—N23 | 1.3206 (19) | C22A—N23A | 1.3233 (17) |
C22—H22 | 0.9500 | C22A—H22A | 0.9500 |
N23—C25 | 1.459 (2) | N23A—C24A | 1.4596 (18) |
N23—C24 | 1.463 (2) | N23A—C25A | 1.4620 (19) |
C24—H24A | 0.9800 | C24A—H24D | 0.9800 |
C24—H24B | 0.9800 | C24A—H24E | 0.9800 |
C24—H24C | 0.9800 | C24A—H24F | 0.9800 |
C25—H25A | 0.9800 | C25A—H25D | 0.9800 |
C25—H25B | 0.9800 | C25A—H25E | 0.9800 |
C25—H25C | 0.9800 | C25A—H25F | 0.9800 |
| | | |
C1—O2—H2 | 110.9 (18) | C1A—O2A—H2A | 111.1 (15) |
O1—C1—O2 | 123.26 (12) | O1A—C1A—O2A | 122.99 (12) |
O1—C1—C2 | 121.92 (12) | O1A—C1A—C2A | 123.66 (11) |
O2—C1—C2 | 114.80 (11) | O2A—C1A—C2A | 113.34 (11) |
C4i—C2—C3 | 119.96 (12) | C4Aii—C2A—C3A | 120.09 (11) |
C4i—C2—C1 | 115.61 (11) | C4Aii—C2A—C1A | 118.55 (11) |
C3—C2—C1 | 124.43 (12) | C3A—C2A—C1A | 121.36 (11) |
N1—C3—C4 | 120.76 (12) | N1A—C3A—C4A | 121.19 (11) |
N1—C3—C2 | 122.27 (12) | N1A—C3A—C2A | 121.28 (11) |
C4—C3—C2 | 116.94 (12) | C4A—C3A—C2A | 117.41 (11) |
C2i—C4—C3 | 123.10 (12) | C2Aii—C4A—C3A | 122.50 (12) |
C2i—C4—H4 | 118.5 | C2Aii—C4A—H4A | 118.7 |
C3—C4—H4 | 118.5 | C3A—C4A—H4A | 118.7 |
C3—N1—C11 | 126.78 (11) | C3A—N1A—C11A | 125.41 (11) |
C3—N1—H1 | 116.3 (12) | C3A—N1A—H1A | 114.7 (12) |
C11—N1—H1 | 116.5 (12) | C11A—N1A—H1A | 117.3 (12) |
C12—C11—C16 | 119.07 (13) | C16A—C11A—C12A | 119.55 (13) |
C12—C11—N1 | 123.17 (13) | C16A—C11A—N1A | 117.88 (13) |
C16—C11—N1 | 117.70 (13) | C12A—C11A—N1A | 122.49 (13) |
C13—C12—C11 | 119.86 (14) | C13A—C12A—C11A | 119.54 (16) |
C13—C12—H12 | 120.1 | C13A—C12A—H12A | 120.2 |
C11—C12—H12 | 120.1 | C11A—C12A—H12A | 120.2 |
C14—C13—C12 | 120.83 (15) | C14A—C13A—C12A | 120.82 (17) |
C14—C13—H13 | 119.6 | C14A—C13A—H13A | 119.6 |
C12—C13—H13 | 119.6 | C12A—C13A—H13A | 119.6 |
C13—C14—C15 | 119.44 (14) | C15A—C14A—C13A | 119.37 (15) |
C13—C14—H14 | 120.3 | C15A—C14A—H14A | 120.3 |
C15—C14—H14 | 120.3 | C13A—C14A—H14A | 120.3 |
C14—C15—C16 | 120.37 (15) | C14A—C15A—C16A | 120.59 (16) |
C14—C15—H15 | 119.8 | C14A—C15A—H15A | 119.7 |
C16—C15—H15 | 119.8 | C16A—C15A—H15A | 119.7 |
C15—C16—C11 | 120.40 (14) | C11A—C16A—C15A | 120.12 (15) |
C15—C16—H16 | 119.8 | C11A—C16A—H16A | 119.9 |
C11—C16—H16 | 119.8 | C15A—C16A—H16A | 119.9 |
O21—C22—N23 | 122.97 (14) | O21A—C22A—N23A | 124.38 (13) |
O21—C22—H22 | 118.5 | O21A—C22A—H22A | 117.8 |
N23—C22—H22 | 118.5 | N23A—C22A—H22A | 117.8 |
C22—N23—C25 | 121.54 (14) | C22A—N23A—C24A | 120.72 (12) |
C22—N23—C24 | 120.45 (13) | C22A—N23A—C25A | 121.15 (12) |
C25—N23—C24 | 117.90 (13) | C24A—N23A—C25A | 118.07 (11) |
N23—C24—H24A | 109.5 | N23A—C24A—H24D | 109.5 |
N23—C24—H24B | 109.5 | N23A—C24A—H24E | 109.5 |
H24A—C24—H24B | 109.5 | H24D—C24A—H24E | 109.5 |
N23—C24—H24C | 109.5 | N23A—C24A—H24F | 109.5 |
H24A—C24—H24C | 109.5 | H24D—C24A—H24F | 109.5 |
H24B—C24—H24C | 109.5 | H24E—C24A—H24F | 109.5 |
N23—C25—H25A | 109.5 | N23A—C25A—H25D | 109.5 |
N23—C25—H25B | 109.5 | N23A—C25A—H25E | 109.5 |
H25A—C25—H25B | 109.5 | H25D—C25A—H25E | 109.5 |
N23—C25—H25C | 109.5 | N23A—C25A—H25F | 109.5 |
H25A—C25—H25C | 109.5 | H25D—C25A—H25F | 109.5 |
H25B—C25—H25C | 109.5 | H25E—C25A—H25F | 109.5 |
| | | |
O1—C1—C2—C4i | −16.08 (19) | O1A—C1A—C2A—C4Aii | 169.62 (13) |
O2—C1—C2—C4i | 162.28 (12) | O2A—C1A—C2A—C4Aii | −10.74 (17) |
O1—C1—C2—C3 | 164.14 (13) | O1A—C1A—C2A—C3A | −11.3 (2) |
O2—C1—C2—C3 | −17.50 (19) | O2A—C1A—C2A—C3A | 168.36 (12) |
C4i—C2—C3—N1 | −178.85 (12) | C4Aii—C2A—C3A—N1A | −176.25 (12) |
C1—C2—C3—N1 | 0.9 (2) | C1A—C2A—C3A—N1A | 4.67 (19) |
C4i—C2—C3—C4 | −0.9 (2) | C4Aii—C2A—C3A—C4A | −0.2 (2) |
C1—C2—C3—C4 | 178.88 (12) | C1A—C2A—C3A—C4A | −179.24 (11) |
N1—C3—C4—C2i | 178.91 (12) | N1A—C3A—C4A—C2Aii | 176.25 (12) |
C2—C3—C4—C2i | 0.9 (2) | C2A—C3A—C4A—C2Aii | 0.2 (2) |
C4—C3—N1—C11 | 30.1 (2) | C4A—C3A—N1A—C11A | 26.3 (2) |
C2—C3—N1—C11 | −152.02 (13) | C2A—C3A—N1A—C11A | −157.76 (13) |
C3—N1—C11—C12 | 25.2 (2) | C3A—N1A—C11A—C16A | −142.53 (13) |
C3—N1—C11—C16 | −157.69 (13) | C3A—N1A—C11A—C12A | 40.6 (2) |
C16—C11—C12—C13 | 1.7 (2) | C16A—C11A—C12A—C13A | −0.8 (2) |
N1—C11—C12—C13 | 178.77 (13) | N1A—C11A—C12A—C13A | 176.08 (14) |
C11—C12—C13—C14 | −1.4 (2) | C11A—C12A—C13A—C14A | 0.1 (3) |
C12—C13—C14—C15 | 0.0 (2) | C12A—C13A—C14A—C15A | 0.0 (3) |
C13—C14—C15—C16 | 1.2 (2) | C13A—C14A—C15A—C16A | 0.4 (3) |
C14—C15—C16—C11 | −0.8 (2) | C12A—C11A—C16A—C15A | 1.2 (2) |
C12—C11—C16—C15 | −0.6 (2) | N1A—C11A—C16A—C15A | −175.76 (13) |
N1—C11—C16—C15 | −177.83 (13) | C14A—C15A—C16A—C11A | −1.1 (2) |
O21—C22—N23—C25 | 177.31 (15) | O21A—C22A—N23A—C24A | 2.1 (2) |
O21—C22—N23—C24 | 1.2 (2) | O21A—C22A—N23A—C25A | 178.99 (14) |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O21 | 0.93 (3) | 1.60 (3) | 2.5268 (14) | 174 (3) |
C22—H22···O1 | 0.95 | 2.59 | 3.2524 (18) | 127 |
N1—H1···O2 | 0.902 (19) | 2.006 (18) | 2.6805 (15) | 130.5 (16) |
O2A—H2A···O21A | 0.95 (3) | 1.60 (3) | 2.5432 (14) | 173 (2) |
C22A—H22A···O2A | 0.95 | 3.14 | 3.2750 (17) | 90 |
N1A—H1A···O1A | 0.889 (19) | 1.984 (19) | 2.7049 (15) | 137.2 (16) |
C4—H4···O1i | 0.95 | 2.44 | 2.7856 (16) | 101 |
C4A—H4A···O2Aii | 0.95 | 2.35 | 2.7003 (16) | 102 |
C14—H14···O2Aiii | 0.95 | 2.52 | 3.3574 (18) | 146 |
C14A—H14A···O1iv | 0.95 | 2.58 | 3.469 (2) | 157 |
C24—H24A···O21 | 0.98 | 2.34 | 2.7517 (19) | 105 |
C24A—H24D···O21A | 0.98 | 2.36 | 2.7824 (17) | 105 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+2; (iii) x+1, y−1, z−1; (iv) x+1, y, z. |
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