Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phen­oxy]phthalo­nitrile dimethyl sulfoxide monosolvate

The synthesis, structural characterization and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phen­oxy]phthalo­nitrile, a substituted phthalo­nitrile derivative carrying a benzimidazole functional group, are reported.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.042
• wR factor = 0.098
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        49% Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O1 Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of         O2 Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of        C22 Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of        C23 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       S1A      0.123 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C8       -C13             1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00633 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      7.808 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.024 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.65 mm
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        25% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-[4-(1H-Benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

Crystal data

C21H12N4O·C2H6OS	Dx = 1.296 Mg m^−3
Mr = 414.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9474 reflections
a = 20.9154 (11) Å	θ = 1.8–27.0°
b = 11.4208 (6) Å	µ = 0.18 mm^−1
c = 8.8938 (6) Å	T = 296 K
V = 2124.5 (2) Å^3	Prism, yellow
Z = 4	0.65 × 0.56 × 0.47 mm
F(000) = 864

Data collection

Stoe IPDS 2 diffractometer	4660 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2281 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.058
Detector resolution: 6.67 pixels mm^-1	θmax = 27.1°, θmin = 2.0°
rotation method scans	h = −26→22
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.966, Tmax = 0.977	l = −11→11
15225 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0409P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.098	(Δ/σ)max < 0.001
S = 0.83	Δρmax = 0.20 e Å^−3
4660 reflections	Δρmin = −0.12 e Å^−3
281 parameters	Absolute structure: Flack x determined using 771 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.02 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.55296 (11)	0.14556 (16)	0.7814 (2)	0.0869 (9)	0.623 (5)
S1B	0.4957 (2)	0.1452 (4)	0.7420 (4)	0.114 (2)	0.377 (5)
O1	0.39958 (15)	0.4586 (3)	0.0943 (3)	0.0925 (8)
O2	0.53727 (19)	0.1838 (3)	0.6323 (4)	0.1425 (15)
N1	0.69349 (16)	0.3756 (2)	0.2997 (4)	0.0751 (8)
N2	0.64212 (17)	0.2699 (2)	0.4721 (3)	0.0720 (8)
H2	0.611036	0.236598	0.518771	0.086*
N3	0.1249 (2)	0.4056 (4)	0.1258 (7)	0.1429 (19)
N4	0.1428 (2)	0.5716 (5)	0.5187 (7)	0.156 (2)
C1	0.8034 (2)	0.3391 (4)	0.4030 (6)	0.0968 (13)
H1	0.824993	0.380986	0.329242	0.116*
C2	0.8361 (3)	0.2860 (5)	0.5198 (7)	0.1100 (17)
H2A	0.880352	0.293117	0.526112	0.132*
C3	0.8032 (3)	0.2223 (5)	0.6272 (7)	0.1098 (16)
H3	0.826349	0.187242	0.704234	0.132*
C4	0.7380 (3)	0.2085 (4)	0.6256 (6)	0.0957 (13)
H4	0.716824	0.165147	0.698781	0.115*
C5	0.7054 (2)	0.2630 (3)	0.5081 (4)	0.0724 (10)
C6	0.7375 (2)	0.3280 (3)	0.3992 (5)	0.0748 (10)
C7	0.6375 (2)	0.3395 (3)	0.3484 (4)	0.0652 (10)
C8	0.57530 (16)	0.3683 (3)	0.2821 (4)	0.0605 (8)
C9	0.52110 (19)	0.3027 (3)	0.3118 (4)	0.0679 (10)
H9	0.523936	0.237162	0.373482	0.081*
C10	0.46302 (19)	0.3338 (3)	0.2509 (4)	0.0785 (11)
H10	0.427035	0.288323	0.270114	0.094*
C11	0.45811 (19)	0.4303 (4)	0.1630 (4)	0.0716 (10)
C12	0.5104 (2)	0.4970 (4)	0.1317 (5)	0.0783 (11)
H12	0.506725	0.562819	0.070782	0.094*
C13	0.5690 (2)	0.4659 (3)	0.1912 (4)	0.0752 (11)
H13	0.604801	0.511332	0.169824	0.090*
C14	0.3486 (2)	0.4793 (3)	0.1868 (5)	0.0734 (11)
C15	0.2890 (2)	0.4466 (3)	0.1358 (5)	0.0804 (11)
H15	0.284932	0.408992	0.043566	0.096*
C16	0.2358 (2)	0.4694 (4)	0.2210 (6)	0.0827 (12)
C17	0.2414 (2)	0.5253 (4)	0.3584 (5)	0.0845 (12)
C18	0.3018 (2)	0.5574 (4)	0.4094 (5)	0.0890 (12)
H18	0.306198	0.594294	0.502000	0.107*
C19	0.3549 (2)	0.5347 (4)	0.3231 (5)	0.0820 (11)
H19	0.395119	0.556988	0.357067	0.098*
C20	0.1739 (3)	0.4332 (4)	0.1682 (6)	0.1069 (17)
C21	0.1857 (3)	0.5498 (5)	0.4466 (6)	0.1113 (17)
C22	0.5253 (2)	0.0068 (4)	0.8099 (6)	0.1185 (17)
H22A	0.536012	−0.018040	0.909946	0.178*	0.623 (5)
H22B	0.479713	0.005567	0.797600	0.178*	0.623 (5)
H22C	0.544633	−0.045215	0.738362	0.178*	0.623 (5)
H22D	0.497256	−0.022369	0.886737	0.178*	0.377 (5)
H22E	0.527035	−0.048198	0.728417	0.178*	0.377 (5)
H22F	0.567387	0.017228	0.850914	0.178*	0.377 (5)
C23	0.4951 (4)	0.2180 (5)	0.8988 (7)	0.151 (2)
H23A	0.502326	0.196930	1.001908	0.227*	0.623 (5)
H23B	0.499347	0.301270	0.887593	0.227*	0.623 (5)
H23C	0.452845	0.194538	0.869547	0.227*	0.623 (5)
H23D	0.464660	0.183633	0.966396	0.227*	0.377 (5)
H23E	0.536893	0.215626	0.943443	0.227*	0.377 (5)
H23F	0.483454	0.297886	0.879270	0.227*	0.377 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0892 (19)	0.1040 (13)	0.0676 (11)	−0.0240 (11)	−0.0011 (11)	0.0104 (10)
S1B	0.124 (5)	0.131 (3)	0.087 (3)	0.016 (3)	−0.017 (2)	0.002 (2)
O1	0.081 (2)	0.135 (2)	0.0614 (15)	0.0085 (18)	0.0017 (16)	0.0154 (17)
O2	0.159 (4)	0.159 (3)	0.109 (3)	0.021 (3)	0.056 (3)	0.056 (2)
N1	0.068 (2)	0.0793 (19)	0.078 (2)	−0.0039 (17)	0.0160 (19)	−0.0036 (19)
N2	0.078 (2)	0.0676 (19)	0.070 (2)	−0.0024 (17)	0.0048 (19)	−0.0014 (16)
N3	0.097 (3)	0.166 (4)	0.165 (4)	−0.038 (3)	−0.028 (3)	0.051 (4)
N4	0.102 (4)	0.230 (6)	0.135 (4)	0.061 (4)	0.025 (3)	0.029 (4)
C1	0.080 (3)	0.110 (3)	0.100 (3)	0.005 (3)	0.014 (3)	−0.028 (3)
C2	0.079 (3)	0.138 (5)	0.113 (4)	0.030 (3)	−0.003 (4)	−0.042 (4)
C3	0.111 (5)	0.112 (4)	0.106 (4)	0.052 (3)	−0.008 (4)	−0.028 (3)
C4	0.103 (4)	0.083 (3)	0.101 (3)	0.023 (3)	−0.001 (3)	−0.010 (3)
C5	0.084 (3)	0.062 (2)	0.072 (3)	0.014 (2)	0.001 (3)	−0.011 (2)
C6	0.068 (3)	0.078 (3)	0.078 (3)	0.006 (2)	0.009 (2)	−0.019 (2)
C7	0.079 (3)	0.0538 (19)	0.063 (2)	−0.001 (2)	0.011 (2)	−0.0006 (19)
C8	0.070 (2)	0.0558 (19)	0.0556 (19)	−0.0026 (18)	0.010 (2)	−0.0016 (19)
C9	0.079 (3)	0.064 (2)	0.061 (2)	−0.009 (2)	0.008 (2)	0.0118 (18)
C10	0.075 (3)	0.085 (3)	0.076 (3)	−0.013 (2)	0.008 (2)	0.010 (2)
C11	0.071 (3)	0.087 (3)	0.057 (2)	0.007 (2)	0.006 (2)	0.010 (2)
C12	0.084 (3)	0.076 (3)	0.075 (3)	0.002 (2)	0.007 (2)	0.020 (2)
C13	0.081 (3)	0.067 (2)	0.077 (3)	−0.008 (2)	0.011 (2)	0.007 (2)
C14	0.074 (3)	0.085 (3)	0.062 (2)	0.003 (2)	−0.004 (2)	0.022 (2)
C15	0.084 (3)	0.086 (3)	0.071 (3)	−0.005 (2)	−0.013 (2)	0.020 (2)
C16	0.067 (3)	0.087 (3)	0.094 (3)	−0.004 (2)	−0.007 (3)	0.037 (3)
C17	0.075 (3)	0.099 (3)	0.079 (3)	0.016 (2)	0.000 (3)	0.029 (3)
C18	0.088 (4)	0.106 (3)	0.073 (3)	0.021 (3)	−0.007 (3)	0.007 (3)
C19	0.073 (3)	0.103 (3)	0.071 (3)	0.004 (2)	−0.009 (2)	0.007 (2)
C20	0.085 (3)	0.117 (4)	0.119 (4)	−0.012 (3)	−0.012 (3)	0.050 (3)
C21	0.089 (4)	0.139 (4)	0.106 (4)	0.034 (3)	0.008 (3)	0.034 (3)
C22	0.150 (5)	0.096 (3)	0.110 (4)	−0.009 (3)	0.006 (3)	0.021 (3)
C23	0.231 (7)	0.101 (4)	0.122 (4)	0.003 (4)	0.046 (5)	−0.007 (4)

Geometric parameters (Å, º)

S1A—O2	1.434 (4)	C10—C11	1.356 (5)
S1A—C22	1.706 (5)	C10—H10	0.9300
S1A—C23	1.800 (6)	C11—C12	1.362 (5)
S1B—O2	1.379 (5)	C12—C13	1.381 (5)
S1B—C23	1.624 (7)	C12—H12	0.9300
S1B—C22	1.801 (6)	C13—H13	0.9300
O1—C14	1.367 (5)	C14—C19	1.374 (5)
O1—C11	1.406 (4)	C14—C15	1.378 (5)
N1—C7	1.314 (4)	C15—C16	1.372 (6)
N1—C6	1.388 (5)	C15—H15	0.9300
N2—C7	1.361 (4)	C16—C17	1.384 (6)
N2—C5	1.365 (5)	C16—C20	1.437 (7)
N2—H2	0.8600	C17—C18	1.390 (6)
N3—C20	1.137 (6)	C17—C21	1.433 (7)
N4—C21	1.132 (6)	C18—C19	1.375 (5)
C1—C6	1.384 (6)	C18—H18	0.9300
C1—C2	1.384 (7)	C19—H19	0.9300
C1—H1	0.9300	C22—H22A	0.9600
C2—C3	1.384 (7)	C22—H22B	0.9600
C2—H2A	0.9300	C22—H22C	0.9600
C3—C4	1.372 (7)	C22—H22D	0.9600
C3—H3	0.9300	C22—H22E	0.9600
C4—C5	1.395 (6)	C22—H22F	0.9600
C4—H4	0.9300	C23—H23A	0.9600
C5—C6	1.392 (5)	C23—H23B	0.9600
C7—C8	1.466 (5)	C23—H23C	0.9600
C8—C9	1.384 (5)	C23—H23D	0.9600
C8—C13	1.384 (5)	C23—H23E	0.9600
C9—C10	1.376 (5)	C23—H23F	0.9600
C9—H9	0.9300
O2—S1A—C22	110.0 (3)	C12—C13—C8	121.0 (4)
O2—S1A—C23	104.1 (3)	C12—C13—H13	119.5
C22—S1A—C23	96.5 (3)	C8—C13—H13	119.5
O2—S1B—C23	116.7 (4)	O1—C14—C19	122.5 (4)
O2—S1B—C22	107.6 (4)	O1—C14—C15	117.4 (4)
C23—S1B—C22	99.4 (3)	C19—C14—C15	120.1 (4)
C14—O1—C11	117.2 (3)	C16—C15—C14	120.1 (4)
C7—N1—C6	104.9 (3)	C16—C15—H15	120.0
C7—N2—C5	106.9 (3)	C14—C15—H15	120.0
C7—N2—H2	126.5	C15—C16—C17	120.3 (4)
C5—N2—H2	126.5	C15—C16—C20	119.8 (5)
C6—C1—C2	118.1 (5)	C17—C16—C20	119.9 (5)
C6—C1—H1	120.9	C16—C17—C18	119.2 (5)
C2—C1—H1	120.9	C16—C17—C21	120.3 (5)
C1—C2—C3	120.1 (5)	C18—C17—C21	120.6 (5)
C1—C2—H2A	120.0	C19—C18—C17	120.1 (4)
C3—C2—H2A	120.0	C19—C18—H18	119.9
C4—C3—C2	123.3 (5)	C17—C18—H18	119.9
C4—C3—H3	118.4	C14—C19—C18	120.2 (4)
C2—C3—H3	118.4	C14—C19—H19	119.9
C3—C4—C5	116.2 (5)	C18—C19—H19	119.9
C3—C4—H4	121.9	N3—C20—C16	179.4 (6)
C5—C4—H4	121.9	N4—C21—C17	177.9 (7)
N2—C5—C6	105.9 (4)	S1A—C22—H22A	109.5
N2—C5—C4	132.5 (4)	S1A—C22—H22B	109.5
C6—C5—C4	121.6 (5)	H22A—C22—H22B	109.5
C1—C6—N1	129.8 (4)	S1A—C22—H22C	109.5
C1—C6—C5	120.7 (4)	H22A—C22—H22C	109.5
N1—C6—C5	109.4 (4)	H22B—C22—H22C	109.5
N1—C7—N2	112.8 (4)	S1B—C22—H22D	109.5
N1—C7—C8	126.0 (3)	S1B—C22—H22E	109.5
N2—C7—C8	121.2 (3)	H22D—C22—H22E	109.5
C9—C8—C13	118.0 (4)	S1B—C22—H22F	109.5
C9—C8—C7	122.0 (3)	H22D—C22—H22F	109.5
C13—C8—C7	120.0 (3)	H22E—C22—H22F	109.5
C10—C9—C8	120.6 (4)	S1A—C23—H23A	109.5
C10—C9—H9	119.7	S1A—C23—H23B	109.5
C8—C9—H9	119.7	H23A—C23—H23B	109.5
C11—C10—C9	120.2 (4)	S1A—C23—H23C	109.5
C11—C10—H10	119.9	H23A—C23—H23C	109.5
C9—C10—H10	119.9	H23B—C23—H23C	109.5
C10—C11—C12	120.8 (4)	S1B—C23—H23D	109.5
C10—C11—O1	120.3 (4)	S1B—C23—H23E	109.5
C12—C11—O1	118.8 (4)	H23D—C23—H23E	109.5
C11—C12—C13	119.4 (4)	S1B—C23—H23F	109.5
C11—C12—H12	120.3	H23D—C23—H23F	109.5
C13—C12—H12	120.3	H23E—C23—H23F	109.5
C6—C1—C2—C3	1.1 (7)	C8—C9—C10—C11	−1.2 (6)
C1—C2—C3—C4	−0.3 (7)	C9—C10—C11—C12	1.0 (6)
C2—C3—C4—C5	−0.2 (7)	C9—C10—C11—O1	176.6 (3)
C7—N2—C5—C6	−1.6 (4)	C14—O1—C11—C10	60.5 (5)
C7—N2—C5—C4	177.2 (4)	C14—O1—C11—C12	−123.7 (4)
C3—C4—C5—N2	−178.8 (4)	C10—C11—C12—C13	−0.4 (6)
C3—C4—C5—C6	−0.1 (6)	O1—C11—C12—C13	−176.1 (4)
C2—C1—C6—N1	177.1 (4)	C11—C12—C13—C8	−0.1 (6)
C2—C1—C6—C5	−1.4 (6)	C9—C8—C13—C12	−0.1 (5)
C7—N1—C6—C1	−178.8 (4)	C7—C8—C13—C12	−177.8 (4)
C7—N1—C6—C5	−0.2 (4)	C11—O1—C14—C19	36.2 (5)
N2—C5—C6—C1	179.9 (3)	C11—O1—C14—C15	−146.4 (3)
C4—C5—C6—C1	0.9 (6)	O1—C14—C15—C16	−177.3 (3)
N2—C5—C6—N1	1.1 (4)	C19—C14—C15—C16	0.1 (6)
C4—C5—C6—N1	−177.9 (3)	C14—C15—C16—C17	0.0 (6)
C6—N1—C7—N2	−0.9 (4)	C14—C15—C16—C20	−178.9 (4)
C6—N1—C7—C8	178.9 (3)	C15—C16—C17—C18	−0.3 (6)
C5—N2—C7—N1	1.6 (4)	C20—C16—C17—C18	178.6 (4)
C5—N2—C7—C8	−178.1 (3)	C15—C16—C17—C21	179.5 (4)
N1—C7—C8—C9	161.5 (3)	C20—C16—C17—C21	−1.6 (6)
N2—C7—C8—C9	−18.8 (5)	C16—C17—C18—C19	0.6 (6)
N1—C7—C8—C13	−20.9 (5)	C21—C17—C18—C19	−179.2 (4)
N2—C7—C8—C13	158.9 (3)	O1—C14—C19—C18	177.5 (4)
C13—C8—C9—C10	0.7 (5)	C15—C14—C19—C18	0.2 (5)
C7—C8—C9—C10	178.3 (3)	C17—C18—C19—C14	−0.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.94	2.794 (5)	172
N2—H2···S1A	0.86	2.83	3.614 (4)	152
C9—H9···O2	0.93	2.40	3.175 (5)	141
C23—H23D···N4^i	0.96	2.63	3.500 (9)	151

Symmetry code: (i) −x+1/2, y−1/2, z+1/2.