organic compounds
The molecule of the title compound, C28H24N2O4, in the monoclinic modification shows no significant differences in bond dimensions from those in the reported orthorhombic modification [Gao et al. (2004). Acta Cryst. E60, o1733-o1735]. Two molecules are linked across a center of inversion by a pair of amide-carbonyl hydrogen bonds [2.867 (2) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027291/bt6555sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027291/bt6555Isup2.hkl |
CCDC reference: 259100
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
N-(3,4-dibenzoyl-2,5-dimethylpyrrol-1-yl)-4-methoxybenzamide top
Crystal data top
C28H24N2O4 | F(000) = 952 |
Mr = 452.49 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20917 reflections |
a = 15.643 (3) Å | θ = 3.1–27.5° |
b = 10.258 (2) Å | µ = 0.09 mm−1 |
c = 16.563 (3) Å | T = 298 K |
β = 116.49 (3)° | Prism, yellow |
V = 2378.7 (8) Å3 | 0.40 × 0.27 × 0.21 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5414 independent reflections |
Radiation source: fine-focus sealed tube | 4210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.660, Tmax = 0.982 | k = −13→13 |
22118 measured reflections | l = −20→21 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0708P)2 + 0.5812P] where P = (Fo2 + 2Fc2)/3 |
5414 reflections | (Δ/σ)max = 0.001 |
314 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.7955 (1) | 0.6278 (1) | 0.6418 (1) | 0.0674 (4) | |
O2 | 0.5559 (1) | 0.7915 (1) | 0.6042 (1) | 0.0499 (3) | |
O3 | 0.5253 (1) | 0.2055 (1) | 0.7179 (1) | 0.0659 (4) | |
O4 | 0.1803 (1) | −0.1761 (1) | 0.5078 (1) | 0.0609 (4) | |
N1 | 0.5519 (1) | 0.3793 (1) | 0.6093 (1) | 0.0369 (3) | |
N2 | 0.4856 (1) | 0.2792 (1) | 0.5770 (1) | 0.0410 (3) | |
C1 | 0.6480 (1) | 0.3651 (1) | 0.6355 (1) | 0.0379 (3) | |
C2 | 0.6869 (1) | 0.4880 (1) | 0.6593 (1) | 0.0361 (3) | |
C3 | 0.6106 (1) | 0.5776 (1) | 0.6453 (1) | 0.0347 (3) | |
C4 | 0.5273 (1) | 0.5068 (2) | 0.6145 (1) | 0.0357 (3) | |
C5 | 0.6868 (1) | 0.2376 (2) | 0.6244 (1) | 0.0557 (4) | |
C6 | 0.4278 (1) | 0.5428 (2) | 0.5942 (1) | 0.0469 (4) | |
C7 | 0.7833 (1) | 0.5268 (2) | 0.6746 (1) | 0.0439 (4) | |
C8 | 0.8660 (1) | 0.4415 (2) | 0.7317 (1) | 0.0462 (4) | |
C9 | 0.9458 (1) | 0.4365 (2) | 0.7154 (1) | 0.0594 (5) | |
C10 | 1.0226 (1) | 0.3567 (2) | 0.7689 (2) | 0.0721 (6) | |
C11 | 1.0213 (2) | 0.2870 (2) | 0.8390 (2) | 0.0707 (6) | |
C12 | 0.9436 (2) | 0.2937 (2) | 0.8566 (2) | 0.0674 (6) | |
C13 | 0.8656 (1) | 0.3703 (2) | 0.8027 (1) | 0.0557 (4) | |
C14 | 0.6161 (1) | 0.7200 (1) | 0.6603 (1) | 0.0375 (3) | |
C15 | 0.6932 (1) | 0.7793 (2) | 0.7431 (1) | 0.0433 (4) | |
C16 | 0.7046 (2) | 0.9133 (2) | 0.7449 (2) | 0.0789 (7) | |
C17 | 0.7730 (2) | 0.9739 (3) | 0.8199 (2) | 0.112 (1) | |
C18 | 0.8319 (2) | 0.9007 (3) | 0.8936 (2) | 0.0970 (9) | |
C19 | 0.8218 (2) | 0.7682 (2) | 0.8929 (1) | 0.0723 (6) | |
C20 | 0.7518 (1) | 0.7070 (2) | 0.8182 (1) | 0.0510 (4) | |
C21 | 0.4763 (1) | 0.1953 (2) | 0.6371 (1) | 0.0400 (3) | |
C22 | 0.3996 (1) | 0.0960 (1) | 0.5958 (1) | 0.0367 (3) | |
C23 | 0.4058 (1) | −0.0189 (2) | 0.6438 (1) | 0.0395 (3) | |
C24 | 0.3324 (1) | −0.1077 (2) | 0.6125 (1) | 0.0426 (4) | |
C25 | 0.2508 (1) | −0.0835 (2) | 0.5327 (1) | 0.0432 (4) | |
C26 | 0.2444 (1) | 0.0284 (2) | 0.4833 (1) | 0.0454 (4) | |
C27 | 0.3185 (1) | 0.1175 (2) | 0.5152 (1) | 0.0420 (4) | |
C28 | 0.0921 (2) | −0.1479 (2) | 0.4320 (2) | 0.0789 (7) | |
H2 | 0.467 (1) | 0.260 (2) | 0.521 (1) | 0.044 (5)* | |
H5a | 0.6948 | 0.1811 | 0.6735 | 0.084* | |
H5b | 0.7474 | 0.2510 | 0.6242 | 0.084* | |
H5c | 0.6432 | 0.1985 | 0.5684 | 0.084* | |
H6a | 0.3857 | 0.5201 | 0.5329 | 0.070* | |
H6b | 0.4243 | 0.6349 | 0.6025 | 0.070* | |
H6c | 0.4090 | 0.4966 | 0.6342 | 0.070* | |
H9 | 0.9479 | 0.4859 | 0.6693 | 0.071* | |
H10 | 1.0752 | 0.3507 | 0.7568 | 0.087* | |
H11 | 1.0732 | 0.2350 | 0.8747 | 0.085* | |
H12 | 0.9432 | 0.2470 | 0.9045 | 0.081* | |
H13 | 0.8127 | 0.3738 | 0.8143 | 0.067* | |
H16 | 0.6657 | 0.9627 | 0.6949 | 0.095* | |
H17 | 0.7794 | 1.0641 | 0.8209 | 0.134* | |
H18 | 0.8788 | 0.9416 | 0.9440 | 0.116* | |
H19 | 0.8620 | 0.7192 | 0.9426 | 0.087* | |
H20 | 0.7440 | 0.6171 | 0.8184 | 0.061* | |
H23 | 0.4601 | −0.0352 | 0.6974 | 0.047* | |
H24 | 0.3373 | −0.1840 | 0.6446 | 0.051* | |
H26 | 0.1906 | 0.0434 | 0.4291 | 0.054* | |
H27 | 0.3141 | 0.1927 | 0.4822 | 0.050* | |
H28a | 0.0662 | −0.0687 | 0.4426 | 0.118* | |
H28b | 0.0482 | −0.2182 | 0.4227 | 0.118* | |
H28c | 0.1025 | −0.1380 | 0.3794 | 0.118* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.053 (1) | 0.057 (1) | 0.098 (1) | −0.005 (1) | 0.039 (1) | 0.021 (1) |
O2 | 0.055 (1) | 0.042 (1) | 0.044 (1) | 0.012 (1) | 0.014 (1) | 0.002 (1) |
O3 | 0.073 (1) | 0.072 (1) | 0.033 (1) | −0.031 (1) | 0.006 (1) | 0.002 (1) |
O4 | 0.050 (1) | 0.054 (1) | 0.073 (1) | −0.020 (1) | 0.022 (1) | −0.010 (1) |
N1 | 0.034 (1) | 0.036 (1) | 0.038 (1) | −0.005 (1) | 0.014 (1) | −0.001 (1) |
N2 | 0.042 (1) | 0.042 (1) | 0.034 (1) | −0.015 (1) | 0.012 (1) | −0.004 (1) |
C1 | 0.035 (1) | 0.037 (1) | 0.041 (1) | 0.000 (1) | 0.017 (1) | 0.003 (1) |
C2 | 0.034 (1) | 0.035 (1) | 0.039 (1) | 0.000 (1) | 0.015 (1) | 0.002 (1) |
C3 | 0.032 (1) | 0.037 (1) | 0.034 (1) | −0.001 (1) | 0.013 (1) | 0.000 (1) |
C4 | 0.034 (1) | 0.041 (1) | 0.030 (1) | 0.000 (1) | 0.012 (1) | 0.000 (1) |
C5 | 0.053 (1) | 0.037 (1) | 0.075 (1) | 0.003 (1) | 0.027 (1) | −0.004 (1) |
C6 | 0.034 (1) | 0.058 (1) | 0.045 (1) | 0.002 (1) | 0.014 (1) | −0.003 (1) |
C7 | 0.037 (1) | 0.043 (1) | 0.054 (1) | −0.004 (1) | 0.022 (1) | 0.000 (1) |
C8 | 0.031 (1) | 0.044 (1) | 0.060 (1) | −0.003 (1) | 0.017 (1) | −0.008 (1) |
C9 | 0.040 (1) | 0.065 (1) | 0.076 (1) | −0.005 (1) | 0.028 (1) | −0.013 (1) |
C10 | 0.034 (1) | 0.088 (2) | 0.091 (2) | 0.002 (1) | 0.025 (1) | −0.033 (1) |
C11 | 0.045 (1) | 0.067 (1) | 0.079 (1) | 0.017 (1) | 0.009 (1) | −0.015 (1) |
C12 | 0.051 (1) | 0.065 (1) | 0.069 (1) | 0.013 (1) | 0.011 (1) | 0.004 (1) |
C13 | 0.039 (1) | 0.058 (1) | 0.065 (1) | 0.007 (1) | 0.019 (1) | 0.005 (1) |
C14 | 0.040 (1) | 0.037 (1) | 0.037 (1) | 0.001 (1) | 0.019 (1) | 0.001 (1) |
C15 | 0.046 (1) | 0.040 (1) | 0.042 (1) | −0.007 (1) | 0.018 (1) | −0.002 (1) |
C16 | 0.094 (2) | 0.043 (1) | 0.069 (1) | −0.017 (1) | 0.009 (1) | 0.000 (1) |
C17 | 0.135 (3) | 0.057 (1) | 0.093 (2) | −0.042 (2) | 0.005 (2) | −0.011 (1) |
C18 | 0.103 (2) | 0.089 (2) | 0.064 (1) | −0.047 (2) | 0.007 (1) | −0.018 (3) |
C19 | 0.068 (1) | 0.084 (2) | 0.046 (1) | −0.023 (1) | 0.007 (1) | 0.001 (1) |
C20 | 0.052 (1) | 0.051 (1) | 0.044 (1) | −0.011 (1) | 0.016 (1) | 0.003 (1) |
C21 | 0.038 (1) | 0.040 (1) | 0.037 (1) | −0.005 (1) | 0.012 (1) | −0.001 (1) |
C22 | 0.034 (1) | 0.038 (1) | 0.036 (1) | −0.004 (1) | 0.014 (1) | −0.001 (1) |
C23 | 0.037 (1) | 0.041 (1) | 0.038 (1) | 0.002 (1) | 0.014 (1) | 0.003 (1) |
C24 | 0.046 (1) | 0.035 (1) | 0.050 (1) | 0.000 (1) | 0.023 (1) | 0.003 (1) |
C25 | 0.040 (1) | 0.040 (1) | 0.052 (1) | −0.008 (1) | 0.023 (1) | −0.010 (1) |
C26 | 0.036 (1) | 0.050 (1) | 0.041 (1) | −0.003 (1) | 0.009 (1) | −0.001 (1) |
C27 | 0.040 (1) | 0.041 (1) | 0.041 (1) | −0.002 (1) | 0.014 (1) | 0.004 (1) |
C28 | 0.050 (1) | 0.087 (2) | 0.084 (2) | −0.029 (1) | 0.014 (1) | −0.016 (1) |
Geometric parameters (Å, º) top
O1—C7 | 1.224 (2) | C22—C27 | 1.389 (2) |
O2—C14 | 1.228 (2) | C22—C23 | 1.400 (2) |
O3—C21 | 1.215 (2) | C23—C24 | 1.374 (2) |
O4—C25 | 1.372 (2) | C24—C25 | 1.390 (2) |
O4—C28 | 1.421 (3) | C25—C26 | 1.387 (2) |
N1—N2 | 1.386 (2) | C26—C27 | 1.383 (2) |
N1—C1 | 1.374 (2) | N2—H2 | 0.86 (1) |
N1—C4 | 1.376 (2) | C5—H5a | 0.9600 |
N2—C21 | 1.371 (2) | C5—H5b | 0.9600 |
C1—C2 | 1.378 (2) | C5—H5c | 0.9600 |
C1—C5 | 1.488 (2) | C6—H6a | 0.9600 |
C2—C3 | 1.441 (2) | C6—H6b | 0.9600 |
C2—C7 | 1.468 (2) | C6—H6c | 0.9600 |
C3—C4 | 1.376 (2) | C9—H9 | 0.9300 |
C3—C14 | 1.478 (2) | C10—H10 | 0.9300 |
C4—C6 | 1.486 (2) | C11—H11 | 0.9300 |
C7—C8 | 1.497 (2) | C12—H12 | 0.9300 |
C8—C13 | 1.387 (3) | C13—H13 | 0.9300 |
C8—C9 | 1.390 (2) | C16—H16 | 0.9300 |
C9—C10 | 1.396 (3) | C17—H17 | 0.9300 |
C10—C11 | 1.372 (3) | C18—H18 | 0.9300 |
C11—C12 | 1.371 (3) | C19—H19 | 0.9300 |
C12—C13 | 1.390 (3) | C20—H20 | 0.9300 |
C14—C15 | 1.493 (2) | C23—H23 | 0.9300 |
C15—C16 | 1.385 (3) | C24—H24 | 0.9300 |
C15—C20 | 1.386 (2) | C26—H26 | 0.9300 |
C16—C17 | 1.374 (3) | C27—H27 | 0.9300 |
C17—C18 | 1.379 (4) | C28—H28a | 0.9600 |
C18—C19 | 1.368 (4) | C28—H28b | 0.9600 |
C19—C20 | 1.384 (3) | C28—H28c | 0.9600 |
C21—C22 | 1.487 (2) | ||
C25—O4—C28 | 117.3 (2) | C27—C26—C25 | 119.6 (1) |
C1—N1—C4 | 112.2 (1) | C26—C27—C22 | 120.8 (1) |
C1—N1—N2 | 124.7 (1) | C21—N2—H2 | 123 (1) |
C4—N1—N2 | 123.1 (1) | N1—N2—H2 | 115 (1) |
C21—N2—N1 | 119.2 (1) | C1—C5—H5a | 109.5 |
N1—C1—C2 | 106.0 (1) | C1—C5—H5b | 109.5 |
N1—C1—C5 | 120.2 (1) | H5a—C5—H5b | 109.5 |
C2—C1—C5 | 133.3 (1) | C1—C5—H5c | 109.5 |
C1—C2—C3 | 107.9 (1) | H5a—C5—H5c | 109.5 |
C1—C2—C7 | 125.9 (1) | H5b—C5—H5c | 109.5 |
C3—C2—C7 | 124.6 (1) | C4—C6—H6a | 109.5 |
C4—C3—C2 | 107.6 (1) | C4—C6—H6b | 109.5 |
C4—C3—C14 | 123.9 (1) | H6a—C6—H6b | 109.5 |
C2—C3—C14 | 128.5 (1) | C4—C6—H6c | 109.5 |
C3—C4—N1 | 106.3 (1) | H6a—C6—H6c | 109.5 |
C3—C4—C6 | 132.6 (1) | H6b—C6—H6c | 109.5 |
N1—C4—C6 | 121.0 (1) | C8—C9—H9 | 120.2 |
O1—C7—C2 | 120.3 (2) | C10—C9—H9 | 120.2 |
O1—C7—C8 | 120.9 (2) | C11—C10—H10 | 119.7 |
C2—C7—C8 | 118.8 (1) | C9—C10—H10 | 119.7 |
C13—C8—C9 | 119.3 (2) | C12—C11—H11 | 119.9 |
C13—C8—C7 | 120.9 (2) | C10—C11—H11 | 119.9 |
C9—C8—C7 | 119.8 (3) | C11—C12—H12 | 120.0 |
C8—C9—C10 | 119.5 (2) | C13—C12—H12 | 120.0 |
C11—C10—C9 | 120.5 (2) | C8—C13—H13 | 119.8 |
C12—C11—C10 | 120.2 (2) | C12—C13—H13 | 119.8 |
C11—C12—C13 | 120.0 (2) | C17—C16—H16 | 119.7 |
C8—C13—C12 | 120.4 (2) | C15—C16—H16 | 119.7 |
O2—C14—C3 | 119.7 (1) | C16—C17—H17 | 120.1 |
O2—C14—C15 | 119.0 (1) | C18—C17—H17 | 120.1 |
C3—C14—C15 | 121.3 (1) | C19—C18—H18 | 119.9 |
C16—C15—C20 | 119.0 (2) | C17—C18—H18 | 119.9 |
C16—C15—C14 | 117.9 (2) | C18—C19—H19 | 120.0 |
C20—C15—C14 | 123.1 (2) | C20—C19—H19 | 120.0 |
C17—C16—C15 | 120.6 (2) | C19—C20—H20 | 119.9 |
C16—C17—C18 | 119.8 (2) | C15—C20—H20 | 119.9 |
C19—C18—C17 | 120.3 (2) | C24—C23—H23 | 119.7 |
C18—C19—C20 | 120.1 (2) | C22—C23—H23 | 119.7 |
C19—C20—C15 | 120.2 (2) | C23—C24—H24 | 120.0 |
O3—C21—N2 | 121.7 (1) | C25—C24—H24 | 120.0 |
O3—C21—C22 | 123.3 (1) | C27—C26—H26 | 120.2 |
N2—C21—C22 | 114.9 (1) | C25—C26—H26 | 120.2 |
C27—C22—C23 | 118.8 (1) | C26—C27—H27 | 119.6 |
C27—C22—C21 | 122.5 (1) | C22—C27—H27 | 119.6 |
C23—C22—C21 | 118.5 (1) | O4—C28—H28a | 109.5 |
C24—C23—C22 | 120.6 (1) | O4—C28—H28b | 109.5 |
C23—C24—C25 | 119.9 (2) | H28a—C28—H28b | 109.5 |
O4—C25—C26 | 124.0 (2) | O4—C28—H28c | 109.5 |
O4—C25—C24 | 115.9 (2) | H28a—C28—H28c | 109.5 |
C26—C25—C24 | 120.2 (1) | H28b—C28—H28c | 109.5 |
C1—N1—N2—C21 | 80.5 (2) | C7—C8—C13—C12 | −178.6 (2) |
C4—N1—N2—C21 | −102.8 (2) | C11—C12—C13—C8 | −0.8 (3) |
C4—N1—C1—C2 | 0.6 (2) | C4—C3—C14—O2 | −43.6 (2) |
N2—N1—C1—C2 | 177.6 (1) | C2—C3—C14—O2 | 136.8 (2) |
C4—N1—C1—C5 | −172.8 (1) | C4—C3—C14—C15 | 135.9 (2) |
N2—N1—C1—C5 | 4.2 (2) | C2—C3—C14—C15 | −43.7 (2) |
N1—C1—C2—C3 | −0.9 (2) | O2—C14—C15—C16 | −12.3 (3) |
C5—C1—C2—C3 | 171.2 (2) | C3—C14—C15—C16 | 168.1 (2) |
N1—C1—C2—C7 | −167.1 (1) | O2—C14—C15—C20 | 166.0 (2) |
C5—C1—C2—C7 | 5.0 (3) | C3—C14—C15—C20 | −13.5 (2) |
C1—C2—C3—C4 | 0.9 (2) | C20—C15—C16—C17 | 0.1 (4) |
C7—C2—C3—C4 | 167.3 (1) | C14—C15—C16—C17 | 178.5 (3) |
C1—C2—C3—C14 | −179.5 (1) | C15—C16—C17—C18 | 1.1 (5) |
C7—C2—C3—C14 | −13.0 (2) | C16—C17—C18—C19 | −1.0 (5) |
C2—C3—C4—N1 | −0.5 (2) | C17—C18—C19—C20 | −0.4 (5) |
C14—C3—C4—N1 | 179.8 (1) | C18—C19—C20—C15 | 1.6 (4) |
C2—C3—C4—C6 | 175.4 (2) | C16—C15—C20—C19 | −1.4 (3) |
C14—C3—C4—C6 | −4.3 (2) | C14—C15—C20—C19 | −179.8 (2) |
C1—N1—C4—C3 | −0.1 (2) | N1—N2—C21—O3 | −0.8 (2) |
N2—N1—C4—C3 | −177.1 (1) | N1—N2—C21—C22 | 176.8 (1) |
C1—N1—C4—C6 | −176.5 (1) | O3—C21—C22—C27 | 149.6 (2) |
N2—N1—C4—C6 | 6.4 (2) | N2—C21—C22—C27 | −27.9 (2) |
C1—C2—C7—O1 | 134.2 (2) | O3—C21—C22—C23 | −25.0 (2) |
C3—C2—C7—O1 | −29.8 (2) | N2—C21—C22—C23 | 157.5 (1) |
C1—C2—C7—C8 | −46.5 (2) | C27—C22—C23—C24 | −1.0 (2) |
C3—C2—C7—C8 | 149.5 (2) | C21—C22—C23—C24 | 173.8 (1) |
O1—C7—C8—C13 | 147.3 (2) | C22—C23—C24—C25 | −0.4 (2) |
C2—C7—C8—C13 | −32.0 (2) | C28—O4—C25—C26 | −6.9 (3) |
O1—C7—C8—C9 | −30.7 (3) | C28—O4—C25—C24 | 173.5 (2) |
C2—C7—C8—C9 | 150.0 (2) | C23—C24—C25—O4 | −178.5 (2) |
C13—C8—C9—C10 | 2.1 (3) | C23—C24—C25—C26 | 1.9 (2) |
C7—C8—C9—C10 | −179.9 (2) | O4—C25—C26—C27 | 178.6 (2) |
C8—C9—C10—C11 | −2.2 (3) | C24—C25—C26—C27 | −1.8 (2) |
C9—C10—C11—C12 | 0.9 (3) | C25—C26—C27—C22 | 0.4 (2) |
C10—C11—C12—C13 | 0.6 (3) | C23—C22—C27—C26 | 1.1 (2) |
C9—C8—C13—C12 | −0.6 (3) | C21—C22—C27—C26 | −173.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 (1) | 2.02 (1) | 2.867 (2) | 171 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |