N-(3,4-Di­benzoyl-2,5-di­methyl­pyrrol-1-yl)-4-methoxy­benz­amide

4-Methoxy­benzoyl­hydrazine condenses with benzoyl­acetone to form the title compound, C₂₈H₂₄N₂O₄, a pyrrole that is substituted at all five positions of the five-membered ring. The –N—C(O)—C fragment of the benzoyl­amide unit is twisted by 80.0 (1)° with respect to the pyrrole ring; two mol­ecules are linked across a centre of inversion by a pair of amide–carbonyl hydrogen bonds [N...O = 2.876 (3) Å].

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.062
• wR factor = 0.167
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSTM02_ALERT_3_A  The ratio of expected to reported Tmax/Tmin(RR') is < 0.50
            Tmin and Tmax reported:      0.405     0.983
            Tmin' and Tmax expected:      0.971     0.983
            RR' =      0.417
            Please check that your absorption correction is appropriate.

Author Response: The ratio is given by the ABSCOR program.

PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large .............       0.42

Author Response: The ratio is given by the ABSCOR program.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 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.

3,4-Dibenzoyl-2,5-dimethylpyrrole-N-(4-methoxy)benzamide

Crystal data

C28H24N2O4	F(000) = 1904
Mr = 452.49	Dx = 1.250 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 28613 reflections
a = 16.603 (3) Å	θ = 3.4–27.5°
b = 16.565 (3) Å	µ = 0.08 mm^−1
c = 17.483 (4) Å	T = 295 K
V = 4808 (2) Å^3	Prism, yellow
Z = 8	0.35 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4844 independent reflections
Radiation source: fine-focus sealed tube	2726 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
ω scan	θmax = 26.3°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.405, Tmax = 0.983	k = −20→19
29843 measured reflections	l = −21→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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 1.5206P] where P = (Fo^2 + 2Fc^2)/3
4844 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.48246 (12)	0.24197 (12)	0.69624 (12)	0.0707 (6)
O2	0.52330 (12)	0.57289 (12)	0.67350 (10)	0.0590 (5)
O3	0.71888 (13)	0.35576 (14)	0.48230 (11)	0.0757 (6)
O4	0.78354 (13)	0.32307 (13)	0.12741 (11)	0.0726 (6)
N1	0.56442 (13)	0.38707 (14)	0.51404 (12)	0.0533 (6)
N2	0.59166 (14)	0.37654 (15)	0.43988 (12)	0.0586 (6)
H2	0.5592	0.3809	0.4017	0.070*
C1	0.52762 (16)	0.32735 (16)	0.55605 (15)	0.0526 (7)
C2	0.51223 (16)	0.35948 (16)	0.62705 (14)	0.0489 (6)
C3	0.54134 (15)	0.44159 (16)	0.62664 (14)	0.0476 (6)
C4	0.57488 (16)	0.45669 (16)	0.55621 (15)	0.0501 (6)
C5	0.5042 (2)	0.24865 (19)	0.52046 (19)	0.0771 (9)
H5a	0.4796	0.2147	0.5584	0.116*
H5b	0.5512	0.2225	0.5004	0.116*
H5c	0.4665	0.2583	0.4798	0.116*
C6	0.47054 (16)	0.31493 (17)	0.68873 (15)	0.0523 (7)
C7	0.54042 (15)	0.50217 (17)	0.68825 (14)	0.0486 (6)
C8	0.62012 (17)	0.52680 (18)	0.52497 (15)	0.0607 (8)
H8a	0.6252	0.5675	0.5638	0.091*
H8b	0.5917	0.5486	0.4819	0.091*
H8c	0.6727	0.5096	0.5091	0.091*
C9	0.41469 (16)	0.35788 (16)	0.74086 (15)	0.0522 (7)
C10	0.40600 (19)	0.3310 (2)	0.81563 (17)	0.0679 (8)
H10	0.4356	0.2867	0.8323	0.081*
C11	0.3543 (2)	0.3688 (2)	0.8652 (2)	0.0853 (11)
H11	0.3503	0.3515	0.9157	0.102*
C12	0.3085 (2)	0.4323 (2)	0.8399 (2)	0.0891 (11)
H12	0.2730	0.4576	0.8733	0.107*
C13	0.3145 (2)	0.4591 (2)	0.7656 (2)	0.0779 (9)
H13	0.2826	0.5016	0.7486	0.093*
C14	0.36819 (17)	0.42222 (17)	0.71636 (17)	0.0597 (7)
H14	0.3731	0.4408	0.6664	0.072*
C15	0.56186 (16)	0.47958 (17)	0.76792 (14)	0.0507 (6)
C16	0.61144 (18)	0.41457 (18)	0.78384 (17)	0.0631 (8)
H16	0.6299	0.3817	0.7445	0.076*
C17	0.6334 (2)	0.3988 (2)	0.8591 (2)	0.0871 (11)
H17	0.6672	0.3556	0.8702	0.105*
C18	0.6051 (3)	0.4472 (3)	0.9170 (2)	0.0936 (12)
H18	0.6196	0.4364	0.9673	0.112*
C19	0.5557 (2)	0.5111 (2)	0.90110 (17)	0.0846 (10)
H19	0.5364	0.5431	0.9408	0.102*
C20	0.53434 (19)	0.52834 (19)	0.82733 (15)	0.0647 (8)
H20	0.5016	0.5725	0.8169	0.078*
C21	0.67229 (18)	0.35875 (17)	0.42841 (16)	0.0552 (7)
C22	0.69639 (16)	0.34520 (16)	0.34812 (15)	0.0510 (7)
C23	0.64345 (17)	0.32693 (16)	0.28966 (15)	0.0560 (7)
H23	0.5889	0.3209	0.3005	0.067*
C24	0.67015 (18)	0.31753 (17)	0.21536 (15)	0.0582 (7)
H24	0.6340	0.3050	0.1765	0.070*
C25	0.75159 (17)	0.32702 (16)	0.19920 (15)	0.0551 (7)
C26	0.80584 (18)	0.34259 (17)	0.25764 (16)	0.0600 (7)
H26	0.8605	0.3472	0.2469	0.072*
C27	0.77874 (17)	0.35112 (17)	0.33097 (16)	0.0579 (7)
H27	0.8154	0.3610	0.3701	0.070*
C28	0.7298 (2)	0.3106 (3)	0.06578 (18)	0.1022 (13)
H28a	0.7027	0.2599	0.0722	0.153*
H28b	0.7593	0.3102	0.0186	0.153*
H28c	0.6908	0.3534	0.0647	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0750 (14)	0.0533 (13)	0.0837 (15)	0.0084 (10)	0.0147 (11)	0.0136 (11)
O2	0.0688 (13)	0.0543 (12)	0.0538 (11)	0.0036 (10)	−0.0097 (9)	0.0012 (9)
O3	0.0683 (14)	0.1080 (18)	0.0507 (12)	0.0124 (12)	−0.0099 (10)	0.0060 (11)
O4	0.0798 (15)	0.0841 (15)	0.0540 (12)	−0.0052 (12)	0.0115 (11)	−0.0041 (11)
N1	0.0585 (14)	0.0621 (14)	0.0391 (12)	−0.0021 (12)	0.0015 (10)	0.0007 (11)
N2	0.0553 (14)	0.0828 (17)	0.0378 (12)	0.0073 (13)	−0.0005 (10)	−0.0013 (11)
C1	0.0544 (16)	0.0532 (16)	0.0503 (15)	−0.0039 (13)	−0.0003 (13)	0.0014 (13)
C2	0.0501 (16)	0.0535 (16)	0.0431 (14)	−0.0007 (12)	0.0015 (12)	0.0035 (12)
C3	0.0508 (15)	0.0521 (16)	0.0400 (14)	−0.0025 (12)	−0.0012 (11)	0.0024 (12)
C4	0.0536 (16)	0.0530 (16)	0.0436 (14)	−0.0049 (13)	−0.0044 (12)	0.0023 (12)
C5	0.091 (2)	0.064 (2)	0.076 (2)	−0.0110 (18)	0.0031 (18)	−0.0137 (17)
C6	0.0501 (16)	0.0532 (17)	0.0537 (16)	−0.0015 (13)	−0.0030 (13)	0.0060 (13)
C7	0.0471 (15)	0.0562 (17)	0.0424 (14)	−0.0041 (13)	0.0000 (11)	0.0041 (12)
C8	0.0639 (18)	0.0660 (19)	0.0522 (16)	−0.0082 (15)	−0.0005 (14)	0.0081 (14)
C9	0.0501 (16)	0.0544 (16)	0.0522 (16)	−0.0061 (13)	0.0025 (13)	0.0035 (13)
C10	0.073 (2)	0.073 (2)	0.0585 (18)	−0.0030 (17)	0.0093 (16)	0.0093 (16)
C11	0.101 (3)	0.092 (3)	0.063 (2)	−0.002 (2)	0.023 (2)	0.0033 (19)
C12	0.084 (3)	0.091 (3)	0.093 (3)	−0.004 (2)	0.036 (2)	−0.017 (2)
C13	0.061 (2)	0.072 (2)	0.100 (3)	0.0034 (17)	0.0145 (19)	−0.0017 (19)
C14	0.0544 (17)	0.0590 (17)	0.0655 (18)	−0.0022 (14)	0.0066 (14)	0.0068 (15)
C15	0.0502 (15)	0.0580 (16)	0.0437 (14)	−0.0061 (13)	−0.0014 (12)	0.0048 (13)
C16	0.0631 (19)	0.0652 (19)	0.0610 (18)	−0.0007 (15)	−0.0088 (15)	0.0053 (15)
C17	0.101 (3)	0.088 (2)	0.073 (2)	0.007 (2)	−0.022 (2)	0.024 (2)
C18	0.126 (3)	0.103 (3)	0.052 (2)	−0.011 (3)	−0.018 (2)	0.017 (2)
C19	0.120 (3)	0.087 (3)	0.0467 (18)	−0.009 (2)	0.0027 (18)	0.0020 (17)
C20	0.079 (2)	0.0640 (19)	0.0511 (17)	−0.0061 (16)	0.0036 (15)	0.0021 (15)
C21	0.0575 (17)	0.0585 (17)	0.0497 (16)	0.0014 (14)	0.0000 (14)	0.0049 (13)
C22	0.0513 (16)	0.0543 (16)	0.0473 (15)	0.0026 (13)	0.0000 (12)	0.0015 (12)
C23	0.0516 (16)	0.0605 (17)	0.0560 (17)	−0.0035 (13)	0.0024 (13)	−0.0028 (14)
C24	0.0616 (18)	0.0635 (18)	0.0494 (16)	−0.0049 (15)	−0.0023 (13)	−0.0041 (14)
C25	0.0599 (18)	0.0541 (16)	0.0514 (16)	−0.0010 (14)	0.0092 (14)	−0.0005 (13)
C26	0.0531 (17)	0.0652 (18)	0.0617 (19)	0.0030 (14)	0.0061 (14)	0.0015 (15)
C27	0.0516 (17)	0.0674 (19)	0.0547 (17)	0.0038 (14)	−0.0053 (13)	0.0009 (14)
C28	0.116 (3)	0.139 (4)	0.0524 (19)	−0.024 (3)	0.002 (2)	−0.020 (2)

Geometric parameters (Å, º)

O1—C6	1.232 (3)	C22—C23	1.382 (4)
O2—C7	1.233 (3)	C22—C27	1.403 (4)
O3—C21	1.220 (3)	C23—C24	1.381 (4)
O4—C25	1.364 (3)	C24—C25	1.390 (4)
O4—C28	1.414 (4)	C25—C26	1.386 (4)
N1—N2	1.384 (3)	C26—C27	1.366 (4)
N1—C1	1.375 (3)	N2—H2	0.8600
N1—C4	1.380 (3)	C5—H5a	0.9600
N2—C21	1.385 (3)	C5—H5b	0.9600
C1—C2	1.375 (4)	C5—H5c	0.9600
C1—C5	1.496 (4)	C8—H8a	0.9600
C2—C3	1.443 (4)	C8—H8b	0.9600
C2—C6	1.479 (4)	C8—H8c	0.9600
C3—C4	1.374 (3)	C10—H10	0.9300
C3—C7	1.472 (4)	C11—H11	0.9300
C4—C8	1.487 (4)	C12—H12	0.9300
C6—C9	1.482 (4)	C13—H13	0.9300
C7—C15	1.486 (3)	C14—H14	0.9300
C9—C10	1.389 (4)	C16—H16	0.9300
C9—C14	1.384 (4)	C17—H17	0.9300
C10—C11	1.372 (4)	C18—H18	0.9300
C11—C12	1.372 (5)	C19—H19	0.9300
C12—C13	1.376 (5)	C20—H20	0.9300
C13—C14	1.382 (4)	C23—H23	0.9300
C15—C16	1.384 (4)	C24—H24	0.9300
C15—C20	1.393 (4)	C26—H26	0.9300
C16—C17	1.390 (4)	C27—H27	0.9300
C17—C18	1.374 (5)	C28—H28a	0.9600
C18—C19	1.367 (5)	C28—H28b	0.9600
C19—C20	1.368 (4)	C28—H28c	0.9600
C21—C22	1.477 (4)
C25—O4—C28	117.5 (2)	O4—C25—C26	115.7 (3)
N2—N1—C1	123.7 (2)	O4—C25—C24	124.0 (3)
N2—N1—C4	124.4 (2)	N1—N2—H2	120.7
C1—N1—C4	111.8 (2)	C21—N2—H2	120.7
N1—N2—C21	118.6 (2)	C1—C5—H5a	109.5
N1—C1—C2	106.6 (2)	C1—C5—H5b	109.5
N1—C1—C5	121.4 (2)	H5a—C5—H5b	109.5
C2—C1—C5	131.6 (3)	C1—C5—H5c	109.5
C1—C2—C3	107.3 (2)	H5a—C5—H5c	109.5
C1—C2—C6	123.5 (2)	H5b—C5—H5c	109.5
C3—C2—C6	129.1 (2)	C4—C8—H8a	109.5
C2—C3—C4	108.2 (2)	C4—C8—H8b	109.5
C2—C3—C7	129.4 (2)	H8a—C8—H8b	109.5
C4—C3—C7	122.4 (2)	C4—C8—H8c	109.5
N1—C4—C3	106.0 (2)	H8a—C8—H8c	109.5
N1—C4—C8	121.3 (2)	H8b—C8—H8c	109.5
C3—C4—C8	132.5 (2)	C11—C10—H10	119.5
O1—C6—C2	119.5 (3)	C9—C10—H10	119.5
O1—C6—C9	120.4 (2)	C10—C11—H11	120.2
C2—C6—C9	120.1 (2)	C12—C11—H11	120.2
O2—C7—C3	119.8 (2)	C11—C12—H12	119.6
O2—C7—C15	119.4 (2)	C13—C12—H12	119.6
C3—C7—C15	120.8 (2)	C12—C13—H13	120.3
C6—C9—C10	119.3 (3)	C14—C13—H13	120.3
C6—C9—C14	121.9 (2)	C13—C14—H14	119.7
C14—C9—C10	118.7 (3)	C9—C14—H14	119.7
C11—C10—C9	120.9 (3)	C15—C16—H16	120.2
C10—C11—C12	119.5 (3)	C17—C16—H16	120.2
C11—C12—C13	120.8 (3)	C18—C17—H17	120.1
C12—C13—C14	119.5 (3)	C16—C17—H17	120.1
C13—C14—C9	120.5 (3)	C19—C18—H18	119.8
C7—C15—C16	121.8 (3)	C17—C18—H18	119.8
C7—C15—C20	118.3 (3)	C18—C19—H19	119.7
C16—C15—C20	119.8 (3)	C20—C19—H19	119.7
C15—C16—C17	119.5 (3)	C19—C20—H20	120.1
C18—C17—C16	119.9 (3)	C15—C20—H20	120.1
C19—C18—C17	120.5 (3)	C24—C23—H23	119.5
C18—C19—C20	120.6 (3)	C22—C23—H23	119.5
C19—C20—C15	119.8 (3)	C23—C24—H24	120.3
O3—C21—N2	120.6 (3)	C25—C24—H24	120.3
O3—C21—C22	123.8 (3)	C27—C26—H26	120.1
N2—C21—C22	115.6 (2)	C25—C26—H26	120.1
C21—C22—C23	124.3 (3)	C26—C27—H27	119.5
C21—C22—C27	117.2 (2)	C22—C27—H27	119.5
C23—C22—C27	118.5 (3)	O4—C28—H28a	109.5
C24—C23—C22	121.1 (3)	O4—C28—H28b	109.5
C23—C24—C25	119.4 (3)	H28a—C28—H28b	109.5
C26—C25—C24	120.2 (3)	O4—C28—H28c	109.5
C27—C26—C25	119.8 (3)	H28a—C28—H28c	109.5
C26—C27—C22	120.9 (3)	H28b—C28—H28c	109.5
C1—N1—N2—C21	−96.9 (3)	C9—C10—C11—C12	2.3 (5)
C4—N1—N2—C21	79.1 (3)	C10—C11—C12—C13	−0.7 (6)
C4—N1—C1—C2	1.2 (3)	C11—C12—C13—C14	−1.0 (5)
N2—N1—C1—C2	177.7 (2)	C12—C13—C14—C9	1.2 (5)
C4—N1—C1—C5	175.1 (3)	C10—C9—C14—C13	0.3 (4)
N2—N1—C1—C5	−8.4 (4)	C6—C9—C14—C13	177.6 (3)
N1—C1—C2—C3	−0.1 (3)	O2—C7—C15—C16	−153.1 (3)
C5—C1—C2—C3	−173.1 (3)	C3—C7—C15—C16	25.4 (4)
N1—C1—C2—C6	178.1 (2)	O2—C7—C15—C20	23.5 (4)
C5—C1—C2—C6	5.0 (5)	C3—C7—C15—C20	−158.0 (3)
C1—C2—C3—C4	−1.1 (3)	C20—C15—C16—C17	−0.2 (4)
C6—C2—C3—C4	−179.1 (3)	C7—C15—C16—C17	176.3 (3)
C1—C2—C3—C7	−179.3 (3)	C15—C16—C17—C18	0.7 (5)
C6—C2—C3—C7	2.7 (5)	C16—C17—C18—C19	−0.3 (6)
C2—C3—C4—N1	1.8 (3)	C17—C18—C19—C20	−0.7 (6)
C7—C3—C4—N1	−179.8 (2)	C18—C19—C20—C15	1.2 (5)
C2—C3—C4—C8	−173.8 (3)	C16—C15—C20—C19	−0.8 (4)
C7—C3—C4—C8	4.6 (5)	C7—C15—C20—C19	−177.4 (3)
C1—N1—C4—C3	−1.9 (3)	N1—N2—C21—O3	−3.0 (4)
N2—N1—C4—C3	−178.4 (2)	N1—N2—C21—C22	177.7 (2)
C1—N1—C4—C8	174.3 (2)	O3—C21—C22—C23	161.8 (3)
N2—N1—C4—C8	−2.2 (4)	N2—C21—C22—C23	−18.9 (4)
C1—C2—C6—O1	36.2 (4)	O3—C21—C22—C27	−17.9 (4)
C3—C2—C6—O1	−146.1 (3)	N2—C21—C22—C27	161.4 (2)
C1—C2—C6—C9	−143.6 (3)	C27—C22—C23—C24	−2.3 (4)
C3—C2—C6—C9	34.1 (4)	C21—C22—C23—C24	178.0 (3)
C4—C3—C7—O2	43.3 (4)	C22—C23—C24—C25	−0.3 (4)
C2—C3—C7—O2	−138.7 (3)	C28—O4—C25—C26	−177.4 (3)
C4—C3—C7—C15	−135.2 (3)	C28—O4—C25—C24	1.7 (4)
C2—C3—C7—C15	42.8 (4)	C23—C24—C25—O4	−176.6 (3)
O1—C6—C9—C14	−146.5 (3)	C23—C24—C25—C26	2.6 (4)
C2—C6—C9—C14	33.3 (4)	O4—C25—C26—C27	177.1 (2)
O1—C6—C9—C10	30.7 (4)	C24—C25—C26—C27	−2.0 (4)
C2—C6—C9—C10	−149.5 (3)	C25—C26—C27—C22	−0.7 (4)
C14—C9—C10—C11	−2.0 (5)	C23—C22—C27—C26	2.8 (4)
C6—C9—C10—C11	−179.4 (3)	C21—C22—C27—C26	−177.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86	2.05	2.876 (3)	162

Symmetry code: (i) −x+1, −y+1, −z+1.