Two acyclic imides: 3-bromo-N-(3-bromo­benzo­yl)-N-(pyridin-2-yl)benzamide and 3-bromo-N-(3-bromo­benzo­yl)-N-(pyrimidin-2-yl)benzamide

Desmond, F.; Gallagher, J.F.; Hehir, N.

doi:10.1107/S2056989020014413

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 76| Part 12| December 2020| Pages 1800-1804

https://doi.org/10.1107/S2056989020014413

Open

access

Two acyclic imides: 3-bromo-N-(3-bromobenzoyl)-N-(pyridin-2-yl)benzamide and 3-bromo-N-(3-bromobenzoyl)-N-(pyrimidin-2-yl)benzamide

Féilim Desmond,^a John F. Gallagher ^a ^* and Niall Hehir ^a

^aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland
^*Correspondence e-mail: john.gallagher@dcu.ie

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 23 October 2020; accepted 29 October 2020; online 3 November 2020)

The title compounds, C₁₉H₁₂Br₂N₂O₂ and C₁₈H₁₁Br₂N₃O₂, were synthesized in good yields from condensation reactions of 3-bromobenzoyl chloride with 2-aminopyridine or 2-aminopyrimidine using standard condensation reaction conditions and subsequent column chromatography.

Keywords: bromine; crystal structure; imide; halogen bonding; hydrogen bonding.

CCDC references: 2041345; 2041344

1. Chemical context

Acyclic imide chemistry, as RCON(R′)COR, (where R,R′ are aryl or alkyl groups) has developed over the past 130 years from condensation reactions of benzoyl chlorides with amino-aromatics such as 2-aminopyridines or 2-aminopyrimidines (Marckwald, 1894 ; Tschitschibabin & Bylinkin, 1922 ; Huntress & Walter, 1948 ). From these reactions, a mixture of the benzamide and acyclic imide is usually obtained, with the relative yields of each component dependent on the starting materials and reaction conditions. The imides can also be synthesized directly from a benzamide starting material. The presence of an ortho-N in the benzamide heteroaromatic ring is an important feature needed to obtain the imide derivative in good yields (Mocilac et al., 2010 , 2012 ; Khavasi & Tehrani, 2013 ).

Several RCON(R′)COR structures have been reported (Groom et al., 2016 ) and derive mostly from either R′ = benzene (Baell et al., 2001 ) or R′ = pyridine or pyrimidine groups (Gallagher et al., 2009a ,b ; Mocilac et al., 2018 ). Related imide structures include the haloimide N-(2,4-dichlorophenyl)-2-methyl-N-(2-nitrobenzoyl)benzamide (Saeed et al., 2010 ) or CSD (Groom et al., 2016) refcode LAKXIG. LAKXIG adopts an open imide or anti conformation with respect to the benzoyl rings and is notable for having three different ortho-benzene substituents. QADPER or N-(3-methoxyphenyl)-N-(3-methoxybenzoyl)benzamide, a methoxyimide derivative has been studied in the design and synthesis of type-III mimetics of the ω-conotoxin GVIA polypeptide (Baell et al., 2001) and is similar in structure to several haloaromatic imides (Gallagher et al., 2009a,b; Mocilac et al., 2018; Shukla et al., 2018 ). Kohmoto et al., (2001 ) have described a series of 9-anthryl-N-(naphthylcarbonyl)carboxamides having the syn-type structure and has been used in photocycloaddition reactions. Masu et al., (2005 ) expanded on this research into diimides to develop foldamer chemistry with the central moiety in these imide structures usually being an alkyl aromatic group.

In recent research on macrocyclic imides, we and others have noted the role of the imide hinge in the development of macrocyclic imides (Evans & Gale, 2004 ; Mocilac & Gallagher, 2013 ). Both syn and anti types of acyclic imide conformation have been observed in the macrocycles. It has been noted how this affects the formation of both trezimide and tennimide macrocycles and with the syn conformation essential for trezimide formation (Mocilac & Gallagher, 2013). Further studies are needed to demonstrate the ease with which the two distinct conformations can interconvert in acyclic imides.

2. Structural commentary

From the condensation reaction of meta-BrC₆H₄COCl with 2-aminopyridine and 2-aminopyrimidine, the benzamide and imide products were obtained and separated by standard column chromatography for each reaction. Using 2-aminopyridine, Brmo and Brmod, (I) were obtained and for 2-aminopyrimidine, Brmopz and Brmopzd, (II) were isolated. Brmo and Brmopz are the (1:1) benzamide products, whereas Brmod, (I) and Brmopzd, (II) are the (2:1) acyclic imides. Both (I) and (II) (Figs. 1–2) adopt similar molecular structures to the majority of published structures (Groom et al., 2016; Gallagher et al., 2009a,b) but they differ in their supramolecular features (Figs. 3–7 ). Both molecules lack strong donor groups (no amide group as in the benzamides; Donnelly et al., 2008 ) but have strong acceptors such as O=C and N-heteroaromatic rings that are able to participate in many weaker intermolecular interactions in their crystal structures, not to mention potential π-ring aromatic stacking and C—H⋯π interactions (Martinez & Iverson, 2012 ; Nishio, 2004 ).

Figure 1
An ORTEP view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
An ORTEP view of (II) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3
A schematic diagram of the hydrogen- and halogen-bonding interactions in the crystal structure of (I).

Figure 4
A schematic diagram of the main intermolecular interactions in the crystal structure of (II).

Figure 5
The intermolecular interactions in (I) (C19 H12 Br2 N2 O2′a) with displacement ellipsoids at the 30% level.

Figure 6
Intermolecular interactions in (I) with atoms depicted as their van der Waals spheres.

Figure 7
Intermolecular interactions in (II) (shown with arrows) and with atoms depicted as their van der Waals spheres.

A comparison of acyclic imides and their key torsion angles demonstrates the range of angles observed and the key differences between the syn (carbonyl O⋯O separations of ∼4.5 Å) and anti conformations (O⋯O separations of ∼3.7 Å) in crystal structures (Groom et al., 2016). In (I) the O1⋯O2 distance is 3.871 (3) Å and the O1=C1⋯C2=O2 torsion angle is −109.3 (5)° compared to an O1⋯O2 = 3.646 (5) Å distance and an O1—C1⋯C2=O2 torsion angle of −96.6 (5)° in (II). We have also previously used the cisoid and transoid terminology for the disposition of the two C=O groups; this is used to describe the orientation and direction of the C=O groups/aromatic rings with respect to one another (Mocilac et al., 2018).

3. Supramolecular features

The prevalent anti-conformation imide structural type is demonstrated in the structures of both (I) and (II) and is similar to the molecular structures of the ortho-F (SOLSUI) and meta-F (DOKXOR) imide structures (Gallagher et al., 2009a,b), the chloro- and methyl-imides (Mocilac et al., 2018) and two benzene relatives (Shukla et al., 2018). This contrasts with the syn type as observed in the crystal structure of Mood, a 2-methylbenzoyl imide (Mocilac et al., 2018) and the four recently described SEYSUN/SEYTIC/SEYTOI/SEYTUO structures (Shukla et al., 2018). A key difference between these structures is the central N-pyridine ring in Mood (Gallagher et al., 2009a,b) and N-benzene rings in the SEYSUN-type structures (Shukla et al., 2018).

In (I), the Brmod molecules aggregate as dimers in a cyclical arrangement using the C32—H32⋯Br33ⁱⁱ and C2=O2⋯Br33ⁱⁱ interactions with the R₂¹(6) motif. Two of these combine to form the centrosymmetric R₂²(12) motif as formed by the flanking C=O⋯Br—C halogen-bonding interactions (Figs. 3, 5 and 6). The hydrogen bonding as H32⋯Br33ⁱⁱ has N_C = 0.986 (Table 1) where N_C is the ratio of contact distance/sum of contact radii using data from Bondi (Bondi, 1965 ; Spek, 2020 ). The halogen-bonding geometric details are Br33⋯O2ⁱⁱ = 3.287 Å (symmetry code ii; Table 1) or N_C = 0.975 with C33—Br33⋯O2ⁱⁱ = 156.85 (9)° and Br33⋯(O2=C2)ⁱⁱ = 134.11 (19)° angles. Centrosymmetric C—H⋯O hydrogen-bonding interactions as R₂²(10) link dimers into zigzag chains along the b-axis direction, whereas weak C—H⋯N interactions link chains into ruffled sheets parallel with the (100) plane (Table 2).

Table 1
Hydrogen-bond geometry (Å, °) for Brmod

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.41	3.330 (4)	170
C32—H32⋯Br33ⁱⁱ	0.93	3.01	3.896 (3)	162
C36—H36⋯N22ⁱⁱⁱ	0.93	2.68	3.363 (4)	131
Symmetry codes: (i) ; (ii) ; (iii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °) for Brmopzd

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O1ⁱ	0.93	2.65	3.369 (5)	134
C36—H36⋯O2ⁱⁱ	0.93	2.61	3.375 (5)	140
C12—H12⋯C25ⁱⁱⁱ	0.93	2.76	3.677 (5)	168
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

In (II), the Brmopzd molecules aggregate by weak intermolecular interactions, as two C—H⋯O, two C—H⋯π(arene) and a C—Br⋯π(arene) contact per molecule, to generate a 3D structure (Figs. 4 and 7). The C36—H36⋯O2ⁱⁱ and C25⋯(H12—C25)ⁱⁱ interactions combine together in the aggregation of a pair of tightly bound molecules with graph-set R₂²(15), while the remaining C23—H23⋯O1ⁱ hydrogen bond results in the formation of centrosymmetric dimers in tandem with π–π stacking between the pyrimidyl rings, with shortest contact distances for N22⋯C23ⁱ = 3.429 (6) Å and N22⋯C24ⁱ = 3.464 (7) Å. The C13—Br13⋯π(arene)^iv contact [symmetry code: (iv) $[{1\over 2}]$ + x, $[{5\over 2}]$ − y, z] has a Br13⋯C15^iv distance of 3.550 (6) Å and C13—Br13⋯C15^iv = 149.44 (16)°, where C15^iv represents the closest Br⋯C contact on the arene ring. The N atoms (two pyrimidyl or tertiary amine N) do not participate in intermolecular interactions and the shortest contact is N26⋯H24^v = 2.76 Å [symmetry code: (v) $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, 2 − z) (Spek, 2020).

4. Database survey

A literature search for acyclic imides provides several 2-aminopyridine structures of which DOKXOR a meta-F benzene derivative (Gallagher et al., 2009a) and CIJPET a meta-Cl derivative (Mocilac et al., 2018), are similar to (I) and (II). MEYYUK, an N-anthracene-9-carboxamide derivative (Kohmoto et al., 2001) and MOCTUT or N,N-dibenzoyl-4-chloroaniline structures (Usman et al., 2002 ) are also similar in structure and conformation.

Shukla and co-workers have detailed six halogenated N-benzoyl-N-phenylbenzamides (imides) that adopt both syn and anti conformations in the solid state (Shukla et al., 2018). The reason why they adopt either conformation is not obvious and suggests that a transformation between either conformation as having a low activation energy barrier. Such imide behaviour (in adopting either of the syn or anti structures) has been known for decades although there does not seem to have been much investigation into possible fluxional behaviour and various influences driving towards one particular conformation or other.

5. Synthesis and crystallization:

Compound (I) is Brmod and (II) is Brmopzd. (I) and (II) were synthesized as mixtures together with the (1:1) benzamides and separated from the benzamides by standard column chromatography in good yields.

(I): Yield = 30–40% ¹H NMR (CDCl₃) for (I) with J values in Hz: δ 7.10 (1H, dd, ³J = 7.5, ⁴J = 5, ⁵J = 1), 7.29 (1H, t, ³J = 7.8), 7.33 (1H, t, ³J = 7.9), 7.65 (2H, dq, ³J = 8.4, ⁴J = 1.8, ⁵J = 1), 7.78 (1H, ddd, ³J = 8, ⁴J = 2, ⁵J = 1), 7.90 (1H, dt, ³J = 8, ⁴J = 1), 7.98 (1H, dt, ³J = 7.8, ⁴J = 1), 8.17 (1H, dd, ³J = 1.7), 8.21 (2H, dd, ³J = 5.2, ⁴J = 1), 8.40 (1H, d, ³J = 8.5). IR (ATR): 2921 (m), 1683 (s), 1580 (m). Melting point 418–420 K.

(II): Yield = 45–55%. ¹H NMR (CDCl₃) for (I) with J values in Hz: δ 7.12 (1H, t, ³J = 4.9), 7.18 (2H, t, ³J = 12), 7.56 (2H, ddd, ³J = 8.0, ⁴J = 2.0, ⁵J = 1.0), 7.60 (2H, ddd, ³J = 7.8, ⁴J = 1.7, ⁵J = 1.0), 7.88 (2H, t, ⁴J = 1.6), 8.59 (2H, d, ³J = 4.8). IR (ATR): 3072 (s), 2963 (s), 1719 (s), 1682 (m). Melting point 406–411 K.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms attached to C atoms were treated as riding using the SHELXL14/7 (Sheldrick, 2015b ) defaults at 294 (1) K with C—H = 0.93 Å (aromatic) and U_iso(H) = 1.2U_eq(C) (aromatic).

Table 3
Experimental details

	Brmod	Brmopzd
Crystal data
Chemical formula	C₁₉H₁₂Br₂N₂O₂	C₁₈H₁₁Br₂N₃O₂
M_r	460.13	461.12
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/a
Temperature (K)	294	294
a, b, c (Å)	5.5439 (1), 16.3366 (4), 19.3701 (4)	11.1712 (4), 11.0590 (3), 14.4181 (5)
β (°)	91.459 (2)	102.756 (4)
V (Å³)	1753.75 (6)	1737.28 (10)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	4.64	4.68
Crystal size (mm)	0.43 × 0.35 × 0.18	0.22 × 0.20 × 0.05

Data collection
Diffractometer	Rigaku Xcalibur, Sapphire3, Gemini Ultra	Rigaku Xcalibur, Sapphire3, Gemini Ultra
Absorption correction	Analytical (ABSFAC; Clark & Reid, 1998 )	Analytical (ABSFAC; Clark & Reid, 1998)
T_min, T_max	0.228, 0.493	0.425, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	16613, 4665, 3025	13616, 3865, 2219
R_int	0.037	0.047
(sin θ/λ)_max (Å⁻¹)	0.694	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.085, 1.01	0.052, 0.109, 1.02
No. of reflections	4665	3865
No. of parameters	226	226
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.42	0.89, −0.67
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT14/7 (Sheldrick, 2015a ), SHELXL14/7 (Sheldrick, 2015b) and Mercury (Macrae et al., 2020 ).

Supporting information

CCDC references: 2041345; 2041344

Crystal structure: contains datablocks global, Brmod, Brmopzd. DOI: https://doi.org/10.1107/S2056989020014413/ex2039sup1.cif

Structure factors: contains datablock Brmod. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmodsup2.hkl

Structure factors: contains datablock Brmopzd. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmopzdsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmodsup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmopzdsup5.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmodsup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989020014413/ex2039Brmopzdsup7.cml

checkCIF report

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT14/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL14/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL14/7 (Sheldrick, 2015b).

3-Bromo-N-(3-bromobenzoyl)-N-(pyridin-2-yl)benzamide (Brmod) top

Crystal data top

C₁₉H₁₂Br₂N₂O₂	D_x = 1.743 Mg m⁻³
M_r = 460.13	Melting point: 419 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.5439 (1) Å	Cell parameters from 4432 reflections
b = 16.3366 (4) Å	θ = 2.1–29.5°
c = 19.3701 (4) Å	µ = 4.64 mm⁻¹
β = 91.459 (2)°	T = 294 K
V = 1753.75 (6) Å³	Block, colourless
Z = 4	0.43 × 0.35 × 0.18 mm
F(000) = 904

Data collection top

Rigaku Xcalibur, Sapphire3, Gemini Ultra diffractometer	4665 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 16.0560 pixels mm^-1	θ_max = 29.6°, θ_min = 2.1°
ω scans	h = −7→7
Absorption correction: analytical (ABSFAC; Clark & Reid, 1998)	k = −22→17
T_min = 0.228, T_max = 0.493	l = −26→26
16613 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0295P)² + 0.9875P] where P = (F_o² + 2F_c²)/3
4665 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br13	0.12586 (8)	0.01924 (3)	−0.22896 (2)	0.07723 (16)
Br33	0.25059 (6)	0.58666 (2)	0.07841 (2)	0.04753 (11)
O1	0.2102 (5)	0.05436 (15)	0.05540 (13)	0.0741 (8)
C1	0.2745 (6)	0.11718 (19)	0.02838 (16)	0.0432 (7)
N1	0.2894 (4)	0.19022 (14)	0.06634 (12)	0.0362 (5)
O2	0.1237 (4)	0.27325 (13)	−0.01771 (11)	0.0513 (6)
C2	0.2485 (5)	0.26745 (17)	0.03375 (15)	0.0350 (6)
C11	0.3581 (5)	0.11967 (17)	−0.04341 (15)	0.0393 (7)
C12	0.2308 (6)	0.07512 (18)	−0.09348 (15)	0.0432 (7)
H12	0.0952	0.0451	−0.0820	0.052*
C13	0.3084 (6)	0.0762 (2)	−0.15995 (16)	0.0499 (8)
C14	0.5141 (7)	0.1177 (3)	−0.17788 (19)	0.0648 (10)
H14	0.5647	0.1176	−0.2233	0.078*
C15	0.6432 (7)	0.1592 (3)	−0.1273 (2)	0.0673 (11)
H15	0.7851	0.1859	−0.1384	0.081*
C16	0.5651 (6)	0.1615 (2)	−0.06085 (18)	0.0510 (8)
H16	0.6509	0.1912	−0.0274	0.061*
C21	0.2667 (5)	0.18650 (17)	0.13984 (14)	0.0366 (6)
N22	0.0859 (4)	0.22893 (17)	0.16417 (13)	0.0488 (7)
C23	0.0675 (7)	0.2294 (2)	0.23268 (19)	0.0626 (10)
H23	−0.0594	0.2586	0.2513	0.075*
C24	0.2231 (7)	0.1898 (2)	0.27726 (18)	0.0601 (9)
H24	0.2045	0.1929	0.3248	0.072*
C25	0.4070 (7)	0.1455 (2)	0.24981 (18)	0.0601 (9)
H25	0.5145	0.1170	0.2785	0.072*
C26	0.4310 (6)	0.1437 (2)	0.17975 (16)	0.0494 (8)
H26	0.5550	0.1144	0.1598	0.059*
C31	0.3759 (5)	0.33794 (17)	0.06655 (13)	0.0321 (6)
C32	0.2767 (5)	0.41557 (17)	0.05842 (14)	0.0330 (6)
H32	0.1309	0.4226	0.0344	0.040*
C33	0.3957 (5)	0.48156 (17)	0.08614 (14)	0.0338 (6)
C34	0.6181 (5)	0.47370 (19)	0.11981 (15)	0.0405 (7)
H34	0.6988	0.5193	0.1375	0.049*
C35	0.7172 (5)	0.39622 (19)	0.12645 (15)	0.0399 (7)
H35	0.8668	0.3898	0.1486	0.048*
C36	0.5982 (5)	0.32877 (17)	0.10082 (14)	0.0352 (6)
H36	0.6657	0.2770	0.1063	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br13	0.0878 (3)	0.0939 (3)	0.0490 (2)	0.0319 (2)	−0.0185 (2)	−0.0193 (2)
Br33	0.0583 (2)	0.03904 (17)	0.04500 (18)	0.00725 (15)	−0.00459 (14)	−0.00051 (14)
O1	0.120 (2)	0.0505 (14)	0.0518 (15)	−0.0332 (15)	0.0154 (15)	0.0002 (12)
C1	0.0492 (19)	0.0393 (17)	0.0412 (17)	−0.0064 (14)	0.0016 (14)	0.0031 (14)
N1	0.0388 (14)	0.0361 (13)	0.0336 (13)	0.0011 (10)	0.0005 (10)	0.0022 (10)
O2	0.0563 (13)	0.0443 (12)	0.0518 (13)	0.0085 (10)	−0.0264 (11)	−0.0012 (10)
C2	0.0307 (15)	0.0375 (16)	0.0365 (16)	0.0056 (12)	−0.0020 (12)	0.0006 (13)
C11	0.0455 (17)	0.0330 (15)	0.0396 (17)	0.0059 (13)	0.0039 (13)	0.0023 (13)
C12	0.0483 (18)	0.0386 (17)	0.0428 (18)	0.0066 (14)	0.0017 (14)	−0.0007 (14)
C13	0.058 (2)	0.053 (2)	0.0384 (17)	0.0204 (16)	−0.0013 (15)	−0.0026 (15)
C14	0.064 (2)	0.087 (3)	0.044 (2)	0.019 (2)	0.0157 (18)	0.005 (2)
C15	0.052 (2)	0.087 (3)	0.063 (3)	0.002 (2)	0.0215 (19)	0.010 (2)
C16	0.0432 (19)	0.053 (2)	0.057 (2)	0.0008 (15)	0.0044 (16)	0.0014 (17)
C21	0.0359 (16)	0.0377 (16)	0.0362 (16)	−0.0010 (12)	−0.0007 (12)	0.0025 (13)
N22	0.0435 (15)	0.0615 (18)	0.0418 (15)	0.0131 (13)	0.0082 (12)	0.0034 (13)
C23	0.064 (2)	0.071 (3)	0.054 (2)	0.0150 (19)	0.0177 (19)	−0.0005 (19)
C24	0.079 (3)	0.066 (2)	0.0359 (18)	−0.006 (2)	0.0035 (18)	0.0029 (17)
C25	0.064 (2)	0.072 (2)	0.0439 (19)	0.0064 (19)	−0.0087 (17)	0.0174 (18)
C26	0.0498 (19)	0.054 (2)	0.0446 (18)	0.0146 (16)	0.0012 (15)	0.0084 (16)
C31	0.0269 (14)	0.0395 (15)	0.0299 (14)	0.0024 (12)	0.0010 (11)	0.0031 (12)
C32	0.0270 (13)	0.0423 (16)	0.0295 (13)	0.0029 (12)	−0.0021 (11)	0.0027 (12)
C33	0.0362 (16)	0.0372 (15)	0.0282 (14)	0.0031 (12)	0.0043 (12)	0.0022 (12)
C34	0.0346 (16)	0.0499 (18)	0.0368 (16)	−0.0065 (14)	−0.0015 (12)	−0.0045 (14)
C35	0.0251 (14)	0.057 (2)	0.0373 (16)	0.0006 (13)	−0.0039 (12)	0.0020 (14)
C36	0.0287 (14)	0.0418 (16)	0.0352 (15)	0.0047 (12)	0.0019 (12)	0.0038 (13)

Geometric parameters (Å, º) top

Br13—C13	1.900 (3)	C21—C26	1.371 (4)
Br33—C33	1.900 (3)	N22—C23	1.334 (4)
O1—C1	1.210 (4)	C23—C24	1.368 (5)
C1—N1	1.403 (4)	C23—H23	0.9300
C1—C11	1.478 (4)	C24—C25	1.368 (5)
N1—C2	1.426 (3)	C24—H24	0.9300
N1—C21	1.434 (3)	C25—C26	1.367 (4)
O2—C2	1.203 (3)	C25—H25	0.9300
C2—C31	1.485 (4)	C26—H26	0.9300
C11—C16	1.385 (4)	C31—C32	1.390 (4)
C11—C12	1.390 (4)	C31—C36	1.393 (4)
C12—C13	1.368 (4)	C32—C33	1.367 (4)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.378 (5)	C33—C34	1.386 (4)
C14—C15	1.377 (5)	C34—C35	1.384 (4)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.369 (5)	C35—C36	1.371 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—H16	0.9300	C36—H36	0.9300
C21—N22	1.316 (4)

O1—C1—N1	120.6 (3)	N22—C23—C24	124.2 (3)
O1—C1—C11	122.2 (3)	N22—C23—H23	117.9
N1—C1—C11	117.0 (3)	C24—C23—H23	117.9
C1—N1—C2	120.9 (2)	C23—C24—C25	118.0 (3)
C1—N1—C21	118.6 (2)	C23—C24—H24	121.0
C2—N1—C21	117.4 (2)	C25—C24—H24	121.0
O2—C2—N1	121.2 (3)	C26—C25—C24	119.3 (3)
O2—C2—C31	123.4 (3)	C26—C25—H25	120.3
N1—C2—C31	115.3 (2)	C24—C25—H25	120.3
C16—C11—C12	119.8 (3)	C25—C26—C21	117.9 (3)
C16—C11—C1	121.7 (3)	C25—C26—H26	121.0
C12—C11—C1	118.4 (3)	C21—C26—H26	121.0
C13—C12—C11	118.9 (3)	C32—C31—C36	119.7 (3)
C13—C12—H12	120.6	C32—C31—C2	118.5 (2)
C11—C12—H12	120.6	C36—C31—C2	121.7 (2)
C12—C13—C14	121.7 (3)	C33—C32—C31	119.3 (2)
C12—C13—Br13	118.8 (3)	C33—C32—H32	120.3
C14—C13—Br13	119.5 (3)	C31—C32—H32	120.3
C15—C14—C13	118.8 (3)	C32—C33—C34	121.8 (3)
C15—C14—H14	120.6	C32—C33—Br33	118.8 (2)
C13—C14—H14	120.6	C34—C33—Br33	119.4 (2)
C16—C15—C14	120.7 (3)	C35—C34—C33	118.3 (3)
C16—C15—H15	119.6	C35—C34—H34	120.8
C14—C15—H15	119.6	C33—C34—H34	120.8
C15—C16—C11	120.0 (3)	C36—C35—C34	121.0 (3)
C15—C16—H16	120.0	C36—C35—H35	119.5
C11—C16—H16	120.0	C34—C35—H35	119.5
N22—C21—C26	124.6 (3)	C35—C36—C31	119.9 (3)
N22—C21—N1	114.9 (2)	C35—C36—H36	120.1
C26—C21—N1	120.5 (3)	C31—C36—H36	120.1
C21—N22—C23	116.0 (3)

O1—C1—N1—C2	−149.3 (3)	C1—N1—C21—C26	62.3 (4)
C11—C1—N1—C2	35.3 (4)	C2—N1—C21—C26	−137.4 (3)
O1—C1—N1—C21	10.3 (4)	C26—C21—N22—C23	0.4 (5)
C11—C1—N1—C21	−165.1 (2)	N1—C21—N22—C23	−177.1 (3)
C1—N1—C2—O2	26.1 (4)	C21—N22—C23—C24	0.5 (5)
C21—N1—C2—O2	−133.7 (3)	N22—C23—C24—C25	−1.3 (6)
C1—N1—C2—C31	−152.0 (3)	C23—C24—C25—C26	1.2 (6)
C21—N1—C2—C31	48.1 (3)	C24—C25—C26—C21	−0.4 (5)
O1—C1—C11—C16	−133.9 (3)	N22—C21—C26—C25	−0.4 (5)
N1—C1—C11—C16	41.4 (4)	N1—C21—C26—C25	176.9 (3)
O1—C1—C11—C12	42.8 (4)	O2—C2—C31—C32	28.3 (4)
N1—C1—C11—C12	−141.9 (3)	N1—C2—C31—C32	−153.6 (2)
C16—C11—C12—C13	−2.5 (4)	O2—C2—C31—C36	−147.3 (3)
C1—C11—C12—C13	−179.2 (3)	N1—C2—C31—C36	30.8 (4)
C11—C12—C13—C14	2.5 (5)	C36—C31—C32—C33	−2.0 (4)
C11—C12—C13—Br13	−177.3 (2)	C2—C31—C32—C33	−177.7 (2)
C12—C13—C14—C15	−0.3 (5)	C31—C32—C33—C34	2.7 (4)
Br13—C13—C14—C15	179.5 (3)	C31—C32—C33—Br33	−177.05 (19)
C13—C14—C15—C16	−2.1 (6)	C32—C33—C34—C35	−1.5 (4)
C14—C15—C16—C11	2.1 (6)	Br33—C33—C34—C35	178.3 (2)
C12—C11—C16—C15	0.2 (5)	C33—C34—C35—C36	−0.4 (4)
C1—C11—C16—C15	176.9 (3)	C34—C35—C36—C31	1.0 (4)
C1—N1—C21—N22	−120.1 (3)	C32—C31—C36—C35	0.2 (4)
C2—N1—C21—N22	40.3 (3)	C2—C31—C36—C35	175.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.41	3.330 (4)	170
C32—H32···Br33ⁱⁱ	0.93	3.01	3.896 (3)	162
C36—H36···N22ⁱⁱⁱ	0.93	2.68	3.363 (4)	131

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) x+1, y, z.

3-Bromo-N-(3-bromobenzoyl)-N-(pyrimidin-2-yl)benzamide (Brmopzd) top

Crystal data top

C₁₈H₁₁Br₂N₃O₂	D_x = 1.763 Mg m⁻³
M_r = 461.12	Melting point: 408 K
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 11.1712 (4) Å	Cell parameters from 3165 reflections
b = 11.0590 (3) Å	θ = 3.2–27.8°
c = 14.4181 (5) Å	µ = 4.68 mm⁻¹
β = 102.756 (4)°	T = 294 K
V = 1737.28 (10) Å³	Plate, colourless
Z = 4	0.22 × 0.20 × 0.05 mm
F(000) = 904

Data collection top

Rigaku Xcalibur, Sapphire3, Gemini Ultra diffractometer	3865 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2219 reflections with I > 2σ(I)
Detector resolution: 16.056 pixels mm^-1	R_int = 0.047
ω scans	θ_max = 27.9°, θ_min = 3.2°
Absorption correction: analytical (ABSFAC; Clark & Reid, 1998)	h = −14→14
T_min = 0.425, T_max = 0.801	k = −14→13
13616 measured reflections	l = −18→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0345P)² + 1.6333P] where P = (F_o² + 2F_c²)/3
3865 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br13	0.56862 (6)	1.25414 (5)	0.79435 (5)	0.0721 (2)
Br33	0.38119 (6)	0.32158 (5)	0.48956 (4)	0.0757 (2)
O1	0.4800 (3)	0.8188 (3)	0.9503 (2)	0.0537 (9)
C1	0.4245 (4)	0.8174 (4)	0.8691 (3)	0.0381 (10)
N1	0.3759 (3)	0.7061 (3)	0.8250 (2)	0.0371 (9)
O2	0.4771 (3)	0.7308 (3)	0.7062 (2)	0.0625 (10)
C2	0.3990 (4)	0.6770 (4)	0.7352 (3)	0.0408 (11)
C11	0.3956 (4)	0.9282 (4)	0.8105 (3)	0.0355 (10)
C12	0.4786 (4)	1.0231 (4)	0.8278 (3)	0.0392 (11)
H12	0.5518	1.0153	0.8730	0.047*
C13	0.4518 (4)	1.1282 (4)	0.7777 (3)	0.0428 (11)
C14	0.3428 (5)	1.1429 (4)	0.7130 (4)	0.0546 (13)
H14	0.3251	1.2156	0.6804	0.066*
C15	0.2597 (5)	1.0492 (5)	0.6966 (4)	0.0601 (14)
H15	0.1853	1.0587	0.6531	0.072*
C16	0.2864 (4)	0.9413 (4)	0.7445 (3)	0.0449 (12)
H16	0.2309	0.8775	0.7324	0.054*
C21	0.3492 (4)	0.6130 (3)	0.8853 (3)	0.0330 (10)
N22	0.3981 (3)	0.5060 (3)	0.8759 (3)	0.0434 (9)
C23	0.3708 (5)	0.4203 (4)	0.9333 (3)	0.0519 (13)
H23	0.3987	0.3420	0.9278	0.062*
C24	0.3035 (5)	0.4434 (4)	0.9998 (4)	0.0539 (13)
H24	0.2883	0.3837	1.0412	0.065*
C25	0.2596 (4)	0.5580 (4)	1.0027 (3)	0.0507 (12)
H25	0.2134	0.5762	1.0473	0.061*
N26	0.2803 (3)	0.6456 (3)	0.9440 (3)	0.0427 (9)
C31	0.3208 (4)	0.5834 (3)	0.6777 (3)	0.0332 (10)
C32	0.3740 (4)	0.5108 (4)	0.6202 (3)	0.0382 (10)
H32	0.4567	0.5194	0.6199	0.046*
C33	0.3045 (5)	0.4261 (4)	0.5636 (3)	0.0447 (12)
C34	0.1809 (5)	0.4155 (5)	0.5591 (3)	0.0563 (14)
H34	0.1339	0.3595	0.5186	0.068*
C35	0.1276 (5)	0.4898 (5)	0.6159 (4)	0.0546 (13)
H35	0.0439	0.4837	0.6132	0.066*
C36	0.1967 (4)	0.5727 (4)	0.6763 (3)	0.0426 (11)
H36	0.1606	0.6207	0.7156	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br13	0.0839 (4)	0.0390 (3)	0.0959 (5)	−0.0179 (3)	0.0255 (4)	0.0052 (3)
Br33	0.1132 (5)	0.0612 (4)	0.0532 (3)	0.0186 (3)	0.0194 (3)	−0.0170 (3)
O1	0.065 (2)	0.0410 (18)	0.049 (2)	−0.0105 (17)	−0.0011 (18)	0.0076 (16)
C1	0.037 (3)	0.034 (2)	0.044 (3)	−0.003 (2)	0.010 (2)	0.001 (2)
N1	0.049 (2)	0.0248 (17)	0.041 (2)	−0.0025 (16)	0.0176 (18)	−0.0013 (16)
O2	0.070 (2)	0.054 (2)	0.078 (3)	−0.0242 (18)	0.048 (2)	−0.0217 (18)
C2	0.043 (3)	0.032 (2)	0.054 (3)	−0.001 (2)	0.025 (2)	−0.002 (2)
C11	0.045 (3)	0.030 (2)	0.035 (2)	0.004 (2)	0.015 (2)	0.0014 (18)
C12	0.042 (3)	0.030 (2)	0.047 (3)	−0.001 (2)	0.011 (2)	−0.004 (2)
C13	0.053 (3)	0.029 (2)	0.051 (3)	0.000 (2)	0.021 (3)	0.004 (2)
C14	0.069 (4)	0.038 (3)	0.058 (3)	0.010 (3)	0.016 (3)	0.014 (2)
C15	0.053 (3)	0.052 (3)	0.068 (4)	0.007 (3)	−0.002 (3)	0.010 (3)
C16	0.049 (3)	0.033 (2)	0.052 (3)	0.000 (2)	0.010 (3)	0.004 (2)
C21	0.037 (3)	0.026 (2)	0.036 (2)	−0.0034 (18)	0.007 (2)	0.0040 (18)
N22	0.055 (3)	0.0293 (19)	0.046 (2)	0.0070 (17)	0.0122 (19)	0.0050 (17)
C23	0.064 (4)	0.030 (2)	0.055 (3)	0.002 (2)	0.000 (3)	0.008 (2)
C24	0.061 (3)	0.050 (3)	0.050 (3)	−0.009 (3)	0.012 (3)	0.015 (2)
C25	0.052 (3)	0.054 (3)	0.049 (3)	−0.005 (2)	0.017 (3)	0.005 (2)
N26	0.047 (2)	0.035 (2)	0.050 (2)	−0.0034 (17)	0.021 (2)	−0.0009 (18)
C31	0.036 (3)	0.031 (2)	0.035 (2)	0.0033 (19)	0.013 (2)	0.0061 (18)
C32	0.042 (3)	0.035 (2)	0.040 (3)	0.003 (2)	0.017 (2)	0.004 (2)
C33	0.063 (3)	0.040 (3)	0.029 (3)	0.006 (2)	0.006 (2)	0.003 (2)
C34	0.068 (4)	0.054 (3)	0.041 (3)	−0.010 (3)	−0.002 (3)	0.002 (2)
C35	0.041 (3)	0.070 (4)	0.049 (3)	−0.007 (3)	0.002 (3)	0.016 (3)
C36	0.046 (3)	0.045 (3)	0.040 (3)	0.005 (2)	0.017 (2)	0.006 (2)

Geometric parameters (Å, º) top

Br13—C13	1.887 (4)	C21—N26	1.314 (5)
Br33—C33	1.901 (4)	C21—N22	1.323 (5)
O1—C1	1.199 (5)	N22—C23	1.337 (5)
C1—N1	1.435 (5)	C23—C24	1.367 (6)
C1—C11	1.483 (6)	C23—H23	0.9300
N1—C2	1.413 (5)	C24—C25	1.363 (6)
N1—C21	1.421 (5)	C24—H24	0.9300
O2—C2	1.204 (5)	C25—N26	1.340 (5)
C2—C31	1.483 (6)	C25—H25	0.9300
C11—C16	1.379 (6)	C31—C32	1.381 (5)
C11—C12	1.386 (6)	C31—C36	1.388 (6)
C12—C13	1.366 (6)	C32—C33	1.365 (6)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.370 (7)	C33—C34	1.373 (7)
C14—C15	1.376 (7)	C34—C35	1.384 (7)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.377 (6)	C35—C36	1.378 (6)
C15—H15	0.9300	C35—H35	0.9300
C16—H16	0.9300	C36—H36	0.9300

O1—C1—N1	120.5 (4)	C21—N22—C23	114.5 (4)
O1—C1—C11	123.1 (4)	N22—C23—C24	122.5 (4)
N1—C1—C11	116.3 (4)	N22—C23—H23	118.7
C2—N1—C21	120.1 (3)	C24—C23—H23	118.7
C2—N1—C1	118.2 (3)	C25—C24—C23	116.9 (4)
C21—N1—C1	117.4 (3)	C25—C24—H24	121.5
O2—C2—N1	119.9 (4)	C23—C24—H24	121.5
O2—C2—C31	122.2 (4)	N26—C25—C24	122.7 (5)
N1—C2—C31	117.8 (4)	N26—C25—H25	118.7
C16—C11—C12	119.9 (4)	C24—C25—H25	118.7
C16—C11—C1	121.9 (4)	C21—N26—C25	114.6 (4)
C12—C11—C1	118.1 (4)	C32—C31—C36	120.2 (4)
C13—C12—C11	119.3 (4)	C32—C31—C2	117.6 (4)
C13—C12—H12	120.4	C36—C31—C2	122.1 (4)
C11—C12—H12	120.4	C33—C32—C31	119.7 (4)
C12—C13—C14	121.3 (4)	C33—C32—H32	120.2
C12—C13—Br13	119.7 (4)	C31—C32—H32	120.2
C14—C13—Br13	119.0 (3)	C32—C33—C34	121.3 (4)
C13—C14—C15	119.5 (4)	C32—C33—Br33	119.0 (4)
C13—C14—H14	120.3	C34—C33—Br33	119.6 (4)
C15—C14—H14	120.3	C33—C34—C35	118.7 (5)
C14—C15—C16	120.2 (5)	C33—C34—H34	120.6
C14—C15—H15	119.9	C35—C34—H34	120.6
C16—C15—H15	119.9	C36—C35—C34	121.0 (5)
C15—C16—C11	119.8 (4)	C36—C35—H35	119.5
C15—C16—H16	120.1	C34—C35—H35	119.5
C11—C16—H16	120.1	C35—C36—C31	119.0 (4)
N26—C21—N22	128.7 (4)	C35—C36—H36	120.5
N26—C21—N1	115.3 (4)	C31—C36—H36	120.5
N22—C21—N1	116.0 (4)

O1—C1—N1—C2	−131.1 (4)	C2—N1—C21—N22	28.9 (6)
C11—C1—N1—C2	52.3 (5)	C1—N1—C21—N22	−127.6 (4)
O1—C1—N1—C21	25.8 (6)	N26—C21—N22—C23	1.3 (7)
C11—C1—N1—C21	−150.8 (4)	N1—C21—N22—C23	−179.7 (4)
C21—N1—C2—O2	−141.4 (4)	C21—N22—C23—C24	−3.4 (7)
C1—N1—C2—O2	14.9 (6)	N22—C23—C24—C25	2.9 (7)
C21—N1—C2—C31	41.3 (6)	C23—C24—C25—N26	−0.1 (8)
C1—N1—C2—C31	−162.5 (4)	N22—C21—N26—C25	1.3 (7)
O1—C1—C11—C16	−143.6 (5)	N1—C21—N26—C25	−177.7 (4)
N1—C1—C11—C16	32.9 (6)	C24—C25—N26—C21	−1.9 (7)
O1—C1—C11—C12	32.4 (6)	O2—C2—C31—C32	35.6 (6)
N1—C1—C11—C12	−151.1 (4)	N1—C2—C31—C32	−147.1 (4)
C16—C11—C12—C13	−1.1 (6)	O2—C2—C31—C36	−140.4 (5)
C1—C11—C12—C13	−177.2 (4)	N1—C2—C31—C36	36.9 (6)
C11—C12—C13—C14	2.1 (7)	C36—C31—C32—C33	−1.7 (6)
C11—C12—C13—Br13	−175.8 (3)	C2—C31—C32—C33	−177.8 (4)
C12—C13—C14—C15	−1.4 (7)	C31—C32—C33—C34	3.4 (7)
Br13—C13—C14—C15	176.6 (4)	C31—C32—C33—Br33	−176.9 (3)
C13—C14—C15—C16	−0.4 (8)	C32—C33—C34—C35	−2.3 (7)
C14—C15—C16—C11	1.4 (7)	Br33—C33—C34—C35	177.9 (3)
C12—C11—C16—C15	−0.6 (6)	C33—C34—C35—C36	−0.3 (7)
C1—C11—C16—C15	175.3 (4)	C34—C35—C36—C31	1.8 (7)
C2—N1—C21—N26	−152.0 (4)	C32—C31—C36—C35	−0.8 (6)
C1—N1—C21—N26	51.6 (5)	C2—C31—C36—C35	175.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1ⁱ	0.93	2.65	3.369 (5)	134
C36—H36···O2ⁱⁱ	0.93	2.61	3.375 (5)	140
C12—H12···C25ⁱⁱⁱ	0.93	2.76	3.677 (5)	168

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1/2, −y+3/2, z; (iii) x+1/2, −y+3/2, z.

Funding information

JFG thanks Dublin City University for grants in aid of chemical research for FD. NH thanks Meath County Council and the VEC for a studentship.

References

Baell, J. B., Forsyth, S. A., Gable, R. W., Norton, R. S. & Mulder, R. J. (2001). J. Comput. Aided Mol. Des. 15, 1119–1136. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bondi, A. (1964). J. Phys. Chem. 68, 441–451. CrossRef CAS Web of Science Google Scholar
Clark, R. C. & Reid, J. S. (1998). Comput. Phys. Commun. 111, 243–257. Web of Science CrossRef CAS Google Scholar
Donnelly, K., Gallagher, J. F. & Lough, A. J. (2008). Acta Cryst. C64, o335–o340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Evans, L. S. & Gale, P. A. (2004). Chem. Commun. pp. 1286–1287. Web of Science CSD CrossRef Google Scholar
Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009a). Acta Cryst. E65, o102–o103. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009b). Acta Cryst. E65, o486–o487. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Huntress, E. W. & Walter, H. C. (1948). J. Org. Chem. 13, 735–737. CrossRef PubMed CAS Web of Science Google Scholar
Khavasi, H. R. & Tehrani, A. A. (2013). CrystEngComm, 15, 3222–3235. Web of Science CSD CrossRef CAS Google Scholar
Kohmoto, S., Ono, Y., Masu, H., Yamaguchi, K., Kishikawa, K. & Yamamoto, M. (2001). Org. Lett. 3, 4153–4155. Web of Science CSD CrossRef PubMed CAS Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Marckwald, W. (1894). Ber. Dtsch. Chem. Ges. 27, 1317–1339. CrossRef Google Scholar
Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191–2201. Web of Science CrossRef CAS Google Scholar
Masu, H., Sakai, M., Kishikawa, K., Yamamoto, M., Yamaguchi, K. & Kohmoto, S. (2005). J. Org. Chem. 70, 1423–1431. Web of Science CSD CrossRef PubMed CAS Google Scholar
Mocilac, P., Donnelly, K. & Gallagher, J. F. (2012). Acta Cryst. B68, 189–203. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mocilac, P., Farrell, M., Lough, A. J., Jelsch, C. & Gallagher, J. F. (2018). Struct. Chem. 29, 1153–1164. Web of Science CSD CrossRef CAS Google Scholar
Mocilac, P. & Gallagher, J. F. (2013). J. Org. Chem. 78, 2355–2361. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mocilac, P., Tallon, M., Lough, A. J. & Gallagher, J. F. (2010). CrystEngComm, 12, 3080–3090. Web of Science CSD CrossRef CAS Google Scholar
Nishio, M. (2004). CrystEngComm, 6, 130–158. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Saeed, A., Hussain, S., Abbas, N. & Bolte, M. (2010). J. Chem. Crystallogr. 40, 919–923. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shukla, R., Nayak, S. K., Chopra, D., Reddy, M. K. & Guru Row, T. N. (2018). J. Mol. Struct. 1164, 280–288. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Tschitschibabin, A. E. & Bylinkin, J. G. (1922). Ber. Dtsch. Chem. Ges. A/B, 55, 998–1002. CrossRef Google Scholar
Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Tian, J.-Z., Zhang, Y. & Xu, J.-H. (2002). Acta Cryst. E58, o357–o358. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 76| Part 12| December 2020| Pages 1800-1804

https://doi.org/10.1107/S2056989020014413

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Two acyclic imides: 3-bromo-N-(3-bromo­benzo­yl)-N-(pyridin-2-yl)benzamide and 3-bromo-N-(3-bromo­benzo­yl)-N-(pyrimidin-2-yl)benzamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization:

6. Refinement

Supporting information

Funding information

References

research communications

Two acyclic imides: 3-bromo-N-(3-bromobenzoyl)-N-(pyridin-2-yl)benzamide and 3-bromo-N-(3-bromobenzoyl)-N-(pyrimidin-2-yl)benzamide

3. Supramolecular features