A monoclinic modification of N-(3,4-di­benzoyl-2,5-di­methyl­pyrrol-1-yl)-4-methoxy­benz­amide

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].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.139
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.660     0.982
            Tmin' and Tmax expected:      0.966     0.982
            RR' =      0.683
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.68

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.40 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C17

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Crystal data

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) Å^3	0.40 × 0.27 × 0.21 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0708P)^2 + 0.5812P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86 (1)	2.02 (1)	2.867 (2)	171 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.