organic compounds
3,5-Dibromo-4-carbamoylbenzoic acid 2-propanol monosolvate
aDepartment of Chemistry, University of Minnesota, 207 Pleasant St SE, Minneapolis, MN 55455, USA
*Correspondence e-mail: trit0026@umn.edu
In the title solvated crystal, C8H5Br2NO3·C3H8O, the acid molecules form inversion dimers by pairwise N—H⋯O hydrogen bonds between carbamoyl groups and the carboxyl and carbamoyl groups link to form head-to-tail inversion dimers. The 2-propanol hydroxyl group interposes between adjacent head-tail pairs, resulting in C33(10) chains of hydrogen bonds propagating along [100]. The molecules of 2-propanol are disordered over two sets of sites in a 0.598 (8):0.402 (8) ratio. The best-fit planes of the carbamoyl group and benzene ring are inclined by 88.26 (11)°. This is a greater inclination than was previously reported with CH3, Cl, F or H in place of the Br atoms, although those analogues did not have a para carboxyl group.
Keywords: crystal structure; hydrogen bond; dibromoarene; solvate; benzamide.
CCDC reference: 1525812
Structure description
Although the structure of 2-bromobenzamide is reported twice (Izumi & Okamoto, 1972; Gulyás et al., 2015) in the current version of the Cambridge Structural Database (version 5.42, Nov 2020; Groom et al., 2016), no 2,6-dibromo- or 4-carboxylbenzamides were found. The title compound (I) is an example of both classes, and was accidentally prepared in an attempt to selectively hydrolyze the ester group of a cyano ester (II) (Fig. 1). The target was cyano acid (III), for a study in our laboratory involving co-crystals of (III) with anthracene (Noland et al., 2017).
In the title crystal (Fig. 2), molecules of (I) form typical amide inversion dimers based on pairwise N1—H1A⋯O1 hydrogen bonds (Table 1; Fig. 3). The carboxyl groups do not homo-dimerize. Instead, they participate in amido-carboxy N1—H1B⋯O2 hydrogen bonding that forms head-to-tail inversion dimers about the center of the The solvent molecule of 2-propanol interposes between H3A of the acid group and O1 of the amide group, forming an O3—H3A⋯O4—H4B⋯O1 hydrogen-bonded chain. Excluding amide dimerization, these hydrogen bonds collectively form C33(10) chains propagating along [100]. The 2-propanol molecule is disordered over two sets of sites in a 0.598 (8):0.402 (8) ratio. The Br atoms and benzene ring do not participate in any short interactions.
A dihedral angle of 88.26 (11)° is observed between the best-fit planes of the carbamoyl group (O1/N1/C1) and the benzene ring (C2–C7; Fig. 4). The corresponding angle is also shown for 2,4,6-trimethyl- (IV; Gdaniec et al., 2004), 2,6-dichloro- (V; Mukherjee et al., 2013), 2,6-difluoro- (VI; Rauf et al., 2006), and unsubstituted (VII; Blake et al., 1972) benzamides. Although none of these reported crystals contain a para-carboxyl group, crystal (I) fits the expected trend. The ortho Br atoms cause a carbamoyl inclination slightly larger than the inclination observed with ortho methyl groups, which is in turn larger than inclinations caused by ortho Cl, F, or H atoms.
Synthesis and crystallization
3,5-Dibromo-4-carbamoylbenzoic acid (I): a portion of compound (II) (589 mg, Fig. 1) taken from our prior study (Noland et al., 2017) was placed in a round-bottomed flask with water (5 ml), 2-propanol (5 ml) and NaOH (186 mg). The resulting mixture was refluxed for 1 h, and then cooled to 290 K. Hydrochloric acid (6 M) was added dropwise until the pH of the mixture was less than 4. An off-white precipitate was collected by suction filtration, and then triturated with 2-propanol, giving a white powder (476 mg, 78%), m.p. 528–529 K. 1H NMR (500 MHz, DMSO-d6) δ 13.705 (s, 1H, H3A), 8.124 (s, 1H, H1A or H1B), 8.069 (s, 2H, H4A, H6A), 7.887 (s, 1H, H1B or H1A); 13C NMR (126 MHz, DMSO-d6) δ 166.8 (1 C, C1 or C8), 164.5 (1 C, C8 or C1), 144.3 (1 C, C5), 133.4 (1 C, C2), 132.0 (2 C, C4, C6), 119.7 (2 C, C3, C7); IR (KBr, cm−1) 3442, 3314, 3185, 3088, 2921, 2487, 1719, 1648, 1604, 1542, 1371, 1270, 901, 743; MS (ESI, m/z) [M − H]− calculated for C8H581Br79BrNO3 321.8543, found 321.8549.
Crystallization: a portion of the white powder was dissolved in refluxing 2-propanol and the resulting mixture was incrementally cooled to 268 K over 6 h. Crystals were collected by decantation, and then washed with 2-propanol.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1525812
https://doi.org/10.1107/S2414314621003916/hb4381sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003916/hb4381Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621003916/hb4381Isup3.cml
Data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).C8H5Br2NO3·C3H8O | F(000) = 376 |
Mr = 383.04 | Dx = 1.797 Mg m−3 |
Triclinic, P1 | Melting point: 528 K |
a = 7.2866 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5212 (6) Å | Cell parameters from 2971 reflections |
c = 12.1832 (8) Å | θ = 2.6–27.3° |
α = 71.376 (1)° | µ = 5.73 mm−1 |
β = 81.745 (1)° | T = 173 K |
γ = 83.682 (1)° | Block, colourless |
V = 707.76 (8) Å3 | 0.40 × 0.38 × 0.16 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 2683 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.021 |
φ and ω scans | θmax = 27.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→9 |
Tmin = 0.486, Tmax = 0.746 | k = −11→10 |
8139 measured reflections | l = −15→15 |
3128 independent reflections |
Refinement on F2 | 151 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0296P)2 + 0.5063P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3128 reflections | Δρmax = 0.63 e Å−3 |
201 parameters | Δρmin = −0.90 e Å−3 |
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. Angle of C2/C3/C4/C5/C6/C7 vs. N1/C1/O1 below Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.9373 (0.0020) x - 1.2809 (0.0074) y + 2.6193 (0.0107) z = 5.8890 (0.0086) * 0.0044 (0.0015) C2 * -0.0085 (0.0016) C3 * 0.0048 (0.0015) C4 * 0.0030 (0.0015) C5 * -0.0070 (0.0015) C6 * 0.0033 (0.0015) C7 Rms deviation of fitted atoms = 0.0055 1.3629 (0.0122) x + 7.5482 (0.0167) y + 8.7867 (0.0367) z = 9.5168 (0.0262) Angle to previous plane (with approximate esd) = 88.256 ( 0.113 ) * 0.0000 (0.0000) N1 * 0.0000 (0.0000) C1 * 0.0000 (0.0000) O1 Rms deviation of fitted atoms = 0.0000 |
Refinement. A direct-methods solution was calculated, followed by full-matrix least squares / difference Fourier cycles. All H atoms were placed in calculated positions (C—H = 0.95–1.00 Å, N—H = 0.88 Å, O—H = 0.84 Å) and refined as riding atoms with Uiso(H) set to 1.2 or 1.5Ueq(C/N/O). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.61784 (4) | 0.53550 (3) | 0.84990 (2) | 0.04348 (9) | |
Br2 | 0.61751 (4) | 0.03664 (3) | 0.63196 (2) | 0.04169 (9) | |
O1 | 0.6947 (2) | 0.0875 (2) | 0.90019 (14) | 0.0332 (4) | |
O2 | 0.8164 (3) | 0.6055 (2) | 0.30554 (14) | 0.0405 (4) | |
O3 | 0.8603 (3) | 0.7832 (2) | 0.39910 (15) | 0.0416 (4) | |
H3A | 0.891 (4) | 0.846 (3) | 0.3317 (11) | 0.050* | |
N1 | 0.3942 (3) | 0.1688 (3) | 0.87692 (17) | 0.0327 (4) | |
H1A | 0.355 (4) | 0.097 (3) | 0.9439 (12) | 0.039* | |
H1B | 0.312 (3) | 0.227 (3) | 0.8307 (19) | 0.039* | |
C1 | 0.5730 (3) | 0.1757 (3) | 0.84327 (18) | 0.0252 (4) | |
C2 | 0.6307 (3) | 0.3004 (3) | 0.72637 (17) | 0.0241 (4) | |
C3 | 0.6625 (3) | 0.4624 (3) | 0.71657 (19) | 0.0265 (4) | |
C4 | 0.7250 (3) | 0.5743 (3) | 0.61079 (19) | 0.0278 (5) | |
H4A | 0.748438 | 0.683825 | 0.606128 | 0.033* | |
C5 | 0.7527 (3) | 0.5239 (3) | 0.51214 (18) | 0.0264 (5) | |
C6 | 0.7196 (3) | 0.3647 (3) | 0.51800 (19) | 0.0276 (5) | |
H6A | 0.737311 | 0.331352 | 0.449673 | 0.033* | |
C7 | 0.6603 (3) | 0.2545 (3) | 0.62524 (19) | 0.0256 (4) | |
C8 | 0.8134 (3) | 0.6414 (3) | 0.3944 (2) | 0.0308 (5) | |
O4 | 0.9365 (13) | 0.9719 (9) | 0.1879 (11) | 0.0313 (15) | 0.598 (8) |
H4B | 1.0530 (14) | 0.964 (8) | 0.184 (5) | 0.047* | 0.598 (8) |
C9 | 0.872 (3) | 1.205 (2) | 0.2603 (12) | 0.060 (2) | 0.598 (8) |
H9A | 0.820755 | 1.320374 | 0.241438 | 0.091* | 0.598 (8) |
H9B | 1.000209 | 1.198652 | 0.278449 | 0.091* | 0.598 (8) |
H9C | 0.796644 | 1.135893 | 0.327854 | 0.091* | 0.598 (8) |
C10 | 0.8716 (7) | 1.1441 (5) | 0.1583 (4) | 0.0345 (13) | 0.598 (8) |
H10A | 0.739971 | 1.152928 | 0.141246 | 0.041* | 0.598 (8) |
C11 | 0.9845 (12) | 1.2460 (14) | 0.0493 (7) | 0.0429 (18) | 0.598 (8) |
H11A | 0.979250 | 1.201108 | −0.014763 | 0.064* | 0.598 (8) |
H11B | 1.113936 | 1.241251 | 0.064208 | 0.064* | 0.598 (8) |
H11C | 0.933135 | 1.361577 | 0.028151 | 0.064* | 0.598 (8) |
O4' | 0.978 (2) | 0.9791 (14) | 0.1997 (18) | 0.0313 (15) | 0.402 (8) |
H4C | 1.049 (8) | 0.954 (10) | 0.146 (5) | 0.047* | 0.402 (8) |
C9' | 0.883 (5) | 1.202 (4) | 0.2791 (18) | 0.060 (2) | 0.402 (8) |
H9D | 0.887410 | 1.321374 | 0.265058 | 0.091* | 0.402 (8) |
H9E | 0.938938 | 1.140568 | 0.350651 | 0.091* | 0.402 (8) |
H9F | 0.753869 | 1.174455 | 0.287647 | 0.091* | 0.402 (8) |
C10' | 0.9900 (11) | 1.1550 (7) | 0.1784 (5) | 0.0304 (17) | 0.402 (8) |
H10B | 1.123331 | 1.176385 | 0.174482 | 0.036* | 0.402 (8) |
C11' | 0.9228 (19) | 1.250 (2) | 0.0639 (10) | 0.0429 (18) | 0.402 (8) |
H11D | 0.793361 | 1.227577 | 0.065230 | 0.064* | 0.402 (8) |
H11E | 1.000083 | 1.215842 | 0.001592 | 0.064* | 0.402 (8) |
H11F | 0.931011 | 1.369041 | 0.049729 | 0.064* | 0.402 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0693 (2) | 0.03621 (15) | 0.02540 (13) | −0.00969 (12) | 0.00169 (12) | −0.01126 (10) |
Br2 | 0.05996 (18) | 0.02835 (13) | 0.03767 (15) | −0.01118 (11) | −0.00300 (12) | −0.00992 (11) |
O1 | 0.0278 (8) | 0.0364 (9) | 0.0226 (8) | −0.0049 (7) | −0.0010 (6) | 0.0086 (7) |
O2 | 0.0473 (10) | 0.0395 (10) | 0.0201 (8) | 0.0044 (8) | 0.0024 (7) | 0.0058 (7) |
O3 | 0.0468 (10) | 0.0323 (9) | 0.0294 (9) | −0.0094 (8) | 0.0080 (8) | 0.0101 (7) |
N1 | 0.0295 (10) | 0.0359 (11) | 0.0200 (10) | −0.0038 (8) | 0.0008 (8) | 0.0080 (8) |
C1 | 0.0314 (11) | 0.0240 (10) | 0.0155 (10) | −0.0062 (9) | 0.0000 (8) | 0.0007 (8) |
C2 | 0.0260 (10) | 0.0237 (10) | 0.0170 (10) | −0.0044 (8) | −0.0003 (8) | 0.0016 (8) |
C3 | 0.0309 (11) | 0.0270 (11) | 0.0186 (10) | −0.0023 (9) | −0.0007 (8) | −0.0039 (8) |
C4 | 0.0284 (11) | 0.0238 (10) | 0.0259 (11) | −0.0044 (9) | −0.0024 (9) | 0.0005 (9) |
C5 | 0.0221 (10) | 0.0276 (11) | 0.0195 (10) | −0.0012 (8) | 0.0004 (8) | 0.0053 (8) |
C6 | 0.0295 (11) | 0.0299 (11) | 0.0184 (10) | 0.0003 (9) | −0.0010 (8) | −0.0022 (9) |
C7 | 0.0281 (11) | 0.0231 (10) | 0.0218 (10) | −0.0033 (8) | −0.0011 (8) | −0.0019 (8) |
C8 | 0.0222 (10) | 0.0311 (12) | 0.0246 (11) | 0.0025 (9) | 0.0016 (9) | 0.0080 (9) |
O4 | 0.026 (4) | 0.0233 (10) | 0.034 (3) | −0.0051 (17) | 0.008 (3) | 0.0027 (10) |
C9 | 0.091 (4) | 0.0453 (19) | 0.042 (4) | −0.0020 (19) | 0.009 (4) | −0.016 (3) |
C10 | 0.036 (3) | 0.027 (2) | 0.035 (2) | 0.0005 (17) | −0.0004 (19) | −0.0050 (17) |
C11 | 0.059 (6) | 0.0292 (15) | 0.032 (2) | −0.001 (4) | 0.000 (3) | 0.0010 (18) |
O4' | 0.026 (4) | 0.0233 (10) | 0.034 (3) | −0.0051 (17) | 0.008 (3) | 0.0027 (10) |
C9' | 0.091 (4) | 0.0453 (19) | 0.042 (4) | −0.0020 (19) | 0.009 (4) | −0.016 (3) |
C10' | 0.039 (4) | 0.020 (3) | 0.030 (3) | −0.007 (2) | −0.009 (2) | −0.001 (2) |
C11' | 0.059 (6) | 0.0292 (15) | 0.032 (2) | −0.001 (4) | 0.000 (3) | 0.0010 (18) |
Br1—C3 | 1.893 (2) | C9—C10 | 1.492 (10) |
Br2—C7 | 1.890 (2) | C9—H9A | 0.9800 |
O1—C1 | 1.236 (3) | C9—H9B | 0.9800 |
O2—C8 | 1.213 (3) | C9—H9C | 0.9800 |
O3—C8 | 1.311 (3) | C10—C11 | 1.517 (8) |
O3—H3A | 0.839 (3) | C10—H10A | 1.0000 |
N1—C1 | 1.311 (3) | C11—H11A | 0.9800 |
N1—H1A | 0.880 (3) | C11—H11B | 0.9800 |
N1—H1B | 0.880 (3) | C11—H11C | 0.9800 |
C1—C2 | 1.515 (3) | O4'—C10' | 1.448 (11) |
C2—C3 | 1.389 (3) | O4'—H4C | 0.840 (3) |
C2—C7 | 1.390 (3) | C9'—C10' | 1.497 (13) |
C3—C4 | 1.385 (3) | C9'—H9D | 0.9800 |
C4—C5 | 1.382 (3) | C9'—H9E | 0.9800 |
C4—H4A | 0.9500 | C9'—H9F | 0.9800 |
C5—C6 | 1.381 (3) | C10'—C11' | 1.492 (12) |
C5—C8 | 1.501 (3) | C10'—H10B | 1.0000 |
C6—C7 | 1.385 (3) | C11'—H11D | 0.9800 |
C6—H6A | 0.9500 | C11'—H11E | 0.9800 |
O4—C10 | 1.437 (8) | C11'—H11F | 0.9800 |
O4—H4B | 0.840 (3) | ||
C8—O3—H3A | 110 (2) | H9A—C9—H9C | 109.5 |
C1—N1—H1A | 119.3 (18) | H9B—C9—H9C | 109.5 |
C1—N1—H1B | 121.2 (18) | O4—C10—C9 | 109.7 (8) |
H1A—N1—H1B | 119 (2) | O4—C10—C11 | 110.9 (7) |
O1—C1—N1 | 124.32 (19) | C9—C10—C11 | 112.8 (10) |
O1—C1—C2 | 118.97 (19) | O4—C10—H10A | 107.8 |
N1—C1—C2 | 116.71 (19) | C9—C10—H10A | 107.8 |
C3—C2—C7 | 117.58 (19) | C11—C10—H10A | 107.8 |
C3—C2—C1 | 121.60 (19) | C10—C11—H11A | 109.5 |
C7—C2—C1 | 120.79 (19) | C10—C11—H11B | 109.5 |
C4—C3—C2 | 121.8 (2) | H11A—C11—H11B | 109.5 |
C4—C3—Br1 | 118.38 (17) | C10—C11—H11C | 109.5 |
C2—C3—Br1 | 119.85 (16) | H11A—C11—H11C | 109.5 |
C5—C4—C3 | 118.9 (2) | H11B—C11—H11C | 109.5 |
C5—C4—H4A | 120.5 | C10'—O4'—H4C | 106 (6) |
C3—C4—H4A | 120.5 | C10'—C9'—H9D | 109.5 |
C6—C5—C4 | 121.02 (19) | C10'—C9'—H9E | 109.5 |
C6—C5—C8 | 117.7 (2) | H9D—C9'—H9E | 109.5 |
C4—C5—C8 | 121.3 (2) | C10'—C9'—H9F | 109.5 |
C5—C6—C7 | 118.9 (2) | H9D—C9'—H9F | 109.5 |
C5—C6—H6A | 120.6 | H9E—C9'—H9F | 109.5 |
C7—C6—H6A | 120.6 | O4'—C10'—C9' | 108.5 (13) |
C6—C7—C2 | 121.8 (2) | O4'—C10'—C11' | 109.7 (10) |
C6—C7—Br2 | 118.33 (17) | C9'—C10'—C11' | 113.5 (14) |
C2—C7—Br2 | 119.82 (15) | O4'—C10'—H10B | 108.3 |
O2—C8—O3 | 124.9 (2) | C9'—C10'—H10B | 108.3 |
O2—C8—C5 | 122.0 (2) | C11'—C10'—H10B | 108.3 |
O3—C8—C5 | 113.2 (2) | C10'—C11'—H11D | 109.5 |
C10—O4—H4B | 109 (5) | C10'—C11'—H11E | 109.5 |
C10—C9—H9A | 109.5 | H11D—C11'—H11E | 109.5 |
C10—C9—H9B | 109.5 | C10'—C11'—H11F | 109.5 |
H9A—C9—H9B | 109.5 | H11D—C11'—H11F | 109.5 |
C10—C9—H9C | 109.5 | H11E—C11'—H11F | 109.5 |
O1—C1—C2—C3 | −91.0 (3) | C4—C5—C6—C7 | −0.9 (3) |
N1—C1—C2—C3 | 89.3 (3) | C8—C5—C6—C7 | −178.9 (2) |
O1—C1—C2—C7 | 86.7 (3) | C5—C6—C7—C2 | 0.9 (3) |
N1—C1—C2—C7 | −93.0 (3) | C5—C6—C7—Br2 | −179.53 (16) |
C7—C2—C3—C4 | −1.3 (3) | C3—C2—C7—C6 | 0.1 (3) |
C1—C2—C3—C4 | 176.4 (2) | C1—C2—C7—C6 | −177.6 (2) |
C7—C2—C3—Br1 | 178.09 (16) | C3—C2—C7—Br2 | −179.40 (16) |
C1—C2—C3—Br1 | −4.2 (3) | C1—C2—C7—Br2 | 2.8 (3) |
C2—C3—C4—C5 | 1.3 (3) | C6—C5—C8—O2 | 7.2 (3) |
Br1—C3—C4—C5 | −178.05 (16) | C4—C5—C8—O2 | −170.8 (2) |
C3—C4—C5—C6 | −0.2 (3) | C6—C5—C8—O3 | −173.2 (2) |
C3—C4—C5—C8 | 177.7 (2) | C4—C5—C8—O3 | 8.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O4 | 0.84 (1) | 1.74 (1) | 2.580 (12) | 174 (3) |
O3—H3A···O4′ | 0.84 (1) | 1.72 (2) | 2.560 (19) | 173 (3) |
N1—H1A···O1i | 0.88 (1) | 2.06 (1) | 2.929 (2) | 171 (3) |
N1—H1B···O2ii | 0.88 (1) | 2.08 (1) | 2.931 (3) | 164 (3) |
O4—H4B···O1iii | 0.84 (1) | 2.05 (3) | 2.802 (11) | 149 (5) |
O4′—H4C···O1iii | 0.84 (1) | 1.90 (5) | 2.606 (18) | 141 (7) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1. |
Acknowledgements
The authors thank Victor G. Young, Jr (X-Ray Crystallographic Laboratory, University of Minnesota) for assistance with the crystallographic determination, and the Wayland E. Noland Research Fellowship Fund at the University of Minnesota for generous financial support of this project.
References
Blake, C. C. F. & Small, R. W. H. (1972). Acta Cryst. B28, 2201–2206. CSD CrossRef IUCr Journals Web of Science Google Scholar
Bruker (2018). APEX3 and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Gdaniec, M., Olszewska, T. & Połoński, T. (2004). Acta Cryst. C60, o41–o43. 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
Gulyás, H., Rivilla, I., Curreli, S., Freixa, Z. & van Leeuwen, P. W. N. M. (2015). Catal. Sci. Technol. 5, 3822–3828. Google Scholar
Izumi, T. & Okamoto, N. (1972). Mem. Chubu Inst. Technol. 8, 139–142. CAS Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals 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
Mukherjee, A., Tothadi, S., Chakraborty, S., Ganguly, S. & Desiraju, G. R. (2013). CrystEngComm, 15, 4640–4654. Web of Science CSD CrossRef CAS Google Scholar
Noland, W. E., Rieger, J. L., Tu, Z. H. & Tritch, K. J. (2017). Acta Cryst. E73, 1743–1746. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rauf, M. K., Badshah, A., Bolte, M. & Saeed, A. (2006). Acta Cryst. E62, o1070–o1071. CSD CrossRef IUCr Journals 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS 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.