Theoretical insight into the disordered structure of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-diphenylethanone: The role of noncovalent interactions
-
Source and publish data:
Acta Crystallographica Section C: Structural Chemistry p. 1058 - 1067 (2018)
Update date:2022-08-23
Topics:
-
Authors:
Tan, Xue-Jie
Wang, Di
Lei, Xu-Gang
Chen, Jun-Peng
Article abstract of DOI:10.1107/S2053229618009762
A global glide disorder has been discovered during an X-ray investigation of the crystal structure of (Z)-2-[(E)-(4-methoxybenzylidene)hydrazinylidene]-1,2-di-phenylethanone (MHDE, C22H18 N2O2) at room temperature. In another crystal, however, such disorder disappears (still at room temperature). Even though the disorder may be partly due to the poor quality of the harvested crystal, the structure can shed light on the nature of disorder. With the help of quantum chemical calculations, it is found that the global disorder seems to be connected with the need for stabilization of the somewhat rigid but mobile and unstable molecular structure. The most relevant feature driving the packing of the disordered structure concerns the slight perturbations (such as glide) of two or more disorder components (fractional occupancies) distributed throughout the crystal.
View More
Full text of DOI:10.1107/S2053229618009762
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information
Volume 74 (2018)
Supporting information for article:
Xue-Jie Tan, Di Wang, Xu-Gang Lei and Jun-Peng Chen
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-1
Theoretical insight into the disordered structure of (Z)-2-((E)-(4-methoxybenzylidene)hydrazono)-1,2-diphenylethanone:the role of
non-covalent interactions
Xue-Jie Tan a
Di Wang , Xu-Gang Lei , Jun-Peng Chen
a
a
a
a
School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, Shandong Province, 250353, P. R. China.
Supporting Information
Corresponding author. Tel.: +86 531 89631208; fax: +86 531 89631207; E-mail addresses: tanxuejie@163.com.
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-2
Table S1 Comparison of bond lengths between three conformers in the crystal structures of o-MHDE and d-MHDE (Å)
bonds i
bond lengths i
1.367(12)
1.368(6)
bonds ii
bond lengths ii
1.375(11)
1.354(11)
1.412(7)
bonds iii
C1—C2
C1—C6
C2—C3
C3—O1
C3—C4
C4—C5
bond lengths iii ΔB iv
ΔB v
ΔB vi
C1A—C2A
C1A—C6A
C2A—C3A
C3A—O1A
C3A—C4A
C4A—C5A
C1B—C2B
C1B—C6B
C2B—C3B
C3B—O1B
C3B—C4B
C4B—C5B
1.360(2)
1.398(2)
1.391(2)
1.3589(18)
1.372(2)
1.385(2)
0.008
0.014
0.006
0.036
0.038
0.006
0.007
0.030
0.027
0.0261
0.015
0.001
0.015
0.044
0.021
0.0099
0.023
0.007
1.418(10)
1.385(6)
1.349(6)
1.357(5)
1.395(5)
1.384(5)
1.378(5)
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-3
C5A—C6A
C6A—C7A
C7A—N1A
C8A—N2A
C8A—C9A
C8A—C15A
C9A—C14A
C9A—C10A
1.379(7)
1.580(7)
1.272(9)
1.306(5)
1.445(6)
1.534(5)
1.375(4)
1.374(12)
C5B—C6B
C6B—C7B
C7B—N1B
C8B—N2B
C8B—C9B
C8B—C15B
C9B—C14B
C9B—C10B
1.370(5)
1.592(7)
1.219(7)
1.219(6)
1.563(7)
1.500(3)
1.387(6)
1.399(7)
C5—C6
1.388(2)
0.009
0.012
0.053
0.087
0.118
0.034
0.012
0.025
0.008
0.016
0.019
0.005
0.005
0.004
0.008
0.049
0.062
0.009
0.127
0.0085
0.0195
0.0301
0.0095
0.011
0.019
0.001
0.019
0.001
0.000
0.0026
0.0026
0.005
0.0149
0.005
0.018
0.139
0.0445
0.0675
0.0879
0.0245
0.001
0.006
0.009
0.003
0.018
0.005
0.0076
0.0014
0.013
0.0341
0.067
C6—C7
1.453(2)
C7—N1
1.2635(19)
1.2865(17)
1.4751(19)
1.5245(18)
1.386(2)
C8—N2
C8—C9
C8—C15
C9—C14
C9—C10
C10—C11
C11—C12
C12—C13
C13—C14
C15—O2
C15—C16
C16—C17
C16—C21
C17—C18
1.393(2)
C10A—C11A 1.386(12)
C11A—C12A 1.394(5)
C12A—C13A 1.364(4)
C13A—C14A 1.381(5)
C10B—C11B 1.394(13)
C11B—C12B 1.378(13)
C12B—C13B 1.383(5)
C13B—C14B 1.376(5)
1.385(2)
1.375(2)
1.365(3)
1.381(2)
C15A—O2A
1.213(2)
C15B—O2B
1.208(3)
1.2156(15)
1.4794(19)
1.3850(18)
1.3911(19)
1.381(2)
C15A—C16A 1.482(3)
C16A—C17A 1.390(3)
C16A—C21A 1.406(3)
C17A—C18A 1.376(4)
C15B—C16B 1.478(3)
C16B—C17B 1.398(3)
C16B—C21B 1.357(3)
C17B—C18B 1.314(4)
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-4
C18A—C19A 1.368(4)
C19A—C20A 1.339(4)
C20A—C21A 1.407(4)
C18B—C19B 1.410(5)
C19B—C20B 1.409(4)
C20B—C21B 1.407(3)
C18—C19
C19—C20
C20—C21
C22—O1
N1—N2
1.368(3)
1.371(3)
1.380(3)
1.419(3)
1.4092(16)
0.042
0.070
0.000
0.062
0.048
0.000
0.032
0.027
0.043
0.0462
0.042
0.038
0.027
0.019
0.0018
C22A—O1A
N1A—N2A
1.462(7)
1.363(8)
C22B—O1B
N1B—N2B
1.400(4)
1.411(4)
i: bonds in part A of d-MHDE.
ii: bonds in part B of d-MHDE.
iii: bonds in o-MHDE.
iv: absolute values of bond length differences between parts A and B of d-MHDE.
v: absolute values of bond length differences between part A of d-MHDE and o-MHDE.
vi: absolute values of bond length differences between part B of d-MHDE and o-MHDE.
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-5
Table S2 Comparison of bond angles between three conformers in the crystal structures of o-MHDE and d-MHDE (°)
bonds i
bond angles i
bonds ii
bond angles ii
bonds iii
bond angles iii
ΔA iv
ΔA v
ΔA vi
C2A—C1A—
C6A
C6B—C1B—
C2B
1
1
1
1
1
1
12.2(6)
21.6(9)
27.6(4)
08.4(6)
23.9(6)
13.8(5)
122.0(6)
C2—C1—C6
120.35(15)
9.80
8.15
1.65
C1A—C2A—
C3A
C1B—C2B—
C3B
117.7(5)
124.2(5)
115.9(4)
119.9(4)
118.7(4)
C1—C2—C3
O1—C3—C4
O1—C3—C2
C4—C3—C2
C3—C4—C5
120.69(16)
124.98(15)
114.92(15)
120.10(15)
119.14(15)
3.90
3.40
7.50
4.00
4.90
0.91
2.62
6.52
3.80
5.34
2.99
0.78
0.98
0.20
0.44
C4A—C3A—
O1A
O1B—
C3B—C4B
O1B—
O1A—
C3A—C2A
C4A—C3A—
C2A
C3B—C2B
C4B—C3B—
C2B
C3A—C4A—
C5A
C5B—C4B—
C3B
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-6
C6A—C5A—
C4A
C6B—C5B—
1
1
1
1
1
1
1
1
20.8(4)
26.6(5)
20.5(5)
12.9(4)
18.1(5)
21.9(4)
20.8(4)
16.8(3)
121.5(4)
119.2(5)
123.3(5)
117.3(4)
112.9(4)
121.5(3)
118.9(3)
118.3(3)
C4—C5—C6
C5—C6—C1
C1—C6—C7
C5—C6—C7
N1—C7—C6
N2—C8—C9
121.40(15)
118.31(14)
121.03(13)
120.64(13)
121.58(13)
120.94(12)
120.14(12)
118.84(11)
0.70
7.40
2.80
4.40
5.20
0.40
1.90
1.50
0.60
8.29
0.53
7.74
3.48
0.96
0.66
2.04
0.10
0.89
2.27
3.34
8.68
0.56
1.24
0.54
C4B
C1A—C6A—
C5A
C1B—C6B—
C5B
C1A—C6A—
C7A
C1B—C6B—
C7B
C5A—C6A—
C7A
C5B—C6B—
C7B
N1A—
N1B—
C7A—C6A
N2A—
C7B—C6B
N2B—
C8A—C9A
N2A—
C8B—C9B
N2B—
N2—C8—
C15
C8A—C15A
C9A—C8A—
C15A
C8B—C15B
C15B—
C9—C8—
C15
C8B—C9B
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-7
C10A—
C14B—
C14—C9—
C10
1
1
1
1
1
1
1
1
13.1(6)
24.1(3)
22.3(6)
27.1(10)
13.2(6)
22.4(3)
17.9(3)
24.1(3)
123.4(6)
117.0(4)
118.3(4)
116.9(6)
120.7(9)
120.0(6)
121.4(5)
117.0(5)
118.35(15)
120.82(13)
120.84(14)
120.08(18)
120.37(19)
120.11(18)
120.02(19)
121.07(18)
10.30
7.10
4.00
10.20
7.50
2.40
3.50
7.10
5.25
3.28
1.46
7.02
7.17
2.29
2.12
3.03
5.05
3.82
2.54
3.18
0.33
0.11
1.38
4.07
C9A—C14A
C14A—
C9B—C10B
C14B—
C14—C9—
C8
C9A—C8A
C10A—
C9B—C8B
C10B—
C10—C9—
C8
C9A—C8A
C9A—
C9B—C8B
C11B—
C11—C10—
C9
C10A—C11A
C10A—
C10B—C9B
C12B—
C12—C11—
C10
C11A—C12A
C13A—
C11B—C10B
C11B—
C13—C12—
C11
C12A—C11A
C12A—
C12B—C13B
C14B—
C12—C13—
C14
C13A—C14A
C9A—
C13B—C12B
C13B—
C13—C14—
C9
C14A—C13A
C14B—C9B
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-8
O2A—
O2B—
O2—C15—
C16
1
1
1
1
1
1
1
1
22.41(19)
19.7(2)
123.76(19)
119.22(19)
117.02(17)
118.71(19)
118.88(18)
122.35(18)
120.9(2)
122.56(12)
118.01(12)
119.39(11)
118.94(14)
121.70(12)
119.36(13)
120.45(15)
120.02(18)
1.35
0.48
0.77
0.97
1.20
2.11
0.70
5.50
0.15
1.69
1.60
0.74
1.62
0.88
1.15
3.22
1.20
1.21
2.37
0.23
2.82
2.99
0.45
2.28
C15A—C16A
O2A—
C15B—C16B
O2B—
O2—C15—
C8
C15A—C8A
C16A—
C15B—C8B
C16B—
C16—C15—
C8
17.79(19)
19.68(19)
20.08(17)
20.24(16)
21.6(2)
C15A—C8A
C17A—
C15B—C8B
C21B—
C17—C16—
C21
C16A—C21A
C17A—
C16B—C17B
C17B—
C17—C16—
C15
C16A—C15A
C21A—
C16B—C15B
C21B—
C21—C16—
C15
C16A—C15A
C18A—
C16B—C15B
C18B—
C18—C17—
C16
C17A—C16A
C19A—
C17B—C16B
C17B—
C19—C18—
C17
16.8(3)
122.3(3)
C18A—C17A
C18B—C19B
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-9
C20A—
C20B—
C18—C19—
C20
1
1
1
1
1
1
24.6(3)
19.3(3)
17.9(2)
13.0(6)
09.2(5)
16.6(4)
118.1(3)
117.6(2)
122.3(2)
111.8(4)
116.3(3)
119.9(4)
120.24(18)
120.40(18)
119.91(16)
6.50
1.70
4.40
1.20
7.10
3.30
4.36
1.10
2.01
1.00
1.34
2.38
2.14
2.80
2.39
2.20
5.76
0.92
C19A—C18A
C19A—
C19B—C18B
C21B—
C19—C20—
C21
C20A—C21A
C16A—
C20B—C19B
C16B—
C20—C21—
C16
C21A—C20A
C7A—
C21B—C20B
C7B—
C7—N1—N2 114.00(12)
C8—N2—N1 110.54(11)
N1A—N2A
C8A—
N1B—N2B
C8B—
N2A—N1A
C3A—
N2B—N1B
C3B—
C3—O1—
118.98(17)
C22
O1A—C22A
O1B—C22B
i: bonds in part A of d-MHDE.
ii: bonds in part B of d-MHDE.
iii: bonds in o-MHDE.
iv: absolute values of bond angle differences between parts A and B of d-MHDE.
v: absolute values of bond angle differences between part A of d-MHDE and o-MHDE.
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-10
vi: absolute values of bond angle differences between part B of d-MHDE and o-MHDE.
Fig. S1 The overlapping of three conformers in the crystal structures of o-MHDE and d-MHDE.
Acta Cryst. (2018). C74, doi:10.1107/S2053229618009762
Supporting information, sup-11
Fig. S2 The intermolecular interactions in various molecule pairings of d-MHDE. The indices I, II, III, IV and V for five molecules are the same as that in Fig. 3. Some molecule pairs such as I-
V, II-III and III-IV are not shown because there are no valuable NCIs between them. Another molecule pair II-V is not shown because all NCIs are the same as that in II-IV.