Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of 5,5-diphenyl-1,3-bis­(prop-2-yn-1-yl)imidazolidine-2,4-dione

The title mol­ecule consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, C—H_Prop...O_Imdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the mol­ecules into infinite chains along the b-axis direction. Two weak C—H_Phen...π inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.090
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.400
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.400 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 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: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5,5-Diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione

Crystal data

C21H16N2O2	F(000) = 344
Mr = 328.36	Dx = 1.247 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.144 (3) Å	Cell parameters from 9652 reflections
b = 7.952 (2) Å	θ = 3.2–27.2°
c = 10.928 (3) Å	µ = 0.08 mm^−1
β = 97.104 (12)°	T = 296 K
V = 874.8 (4) Å^3	Prism, colourless
Z = 2	0.34 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	3529 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 27.5°, θmin = 1.9°
Tmin = 0.694, Tmax = 0.746	h = −13→13
21744 measured reflections	k = −10→10
3988 independent reflections	l = −13→14

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.0829P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.090	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.14 e Å^−3
3988 reflections	Δρmin = −0.16 e Å^−3
290 parameters	Absolute structure: Flack x determined using 1436 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.3 (4)
Primary atom site location: dual

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
O1	0.27390 (15)	0.2664 (2)	0.19321 (15)	0.0502 (4)
O2	−0.01151 (15)	0.7093 (2)	0.18041 (16)	0.0521 (4)
N1	0.10965 (17)	0.4650 (2)	0.16652 (16)	0.0421 (4)
N2	0.20794 (16)	0.6856 (2)	0.26052 (16)	0.0408 (4)
C1	0.30827 (18)	0.5513 (3)	0.27974 (18)	0.0380 (4)
C2	0.2324 (2)	0.4054 (3)	0.20923 (18)	0.0387 (4)
C3	0.09114 (19)	0.6317 (3)	0.20165 (18)	0.0390 (4)
C4	0.33794 (18)	0.5114 (2)	0.41722 (19)	0.0385 (4)
C5	0.2604 (2)	0.3960 (3)	0.4718 (2)	0.0458 (5)
C6	0.2784 (3)	0.3712 (4)	0.5987 (2)	0.0565 (6)
C7	0.3738 (3)	0.4604 (4)	0.6713 (2)	0.0572 (6)
C8	0.4520 (2)	0.5750 (3)	0.6180 (2)	0.0526 (6)
C9	0.4342 (2)	0.6008 (3)	0.4921 (2)	0.0454 (5)
C10	0.42895 (19)	0.5861 (3)	0.21163 (19)	0.0395 (4)
C11	0.5495 (2)	0.5070 (3)	0.2474 (2)	0.0441 (5)
C12	0.6546 (2)	0.5272 (3)	0.1782 (2)	0.0543 (6)
C13	0.6410 (3)	0.6249 (4)	0.0733 (2)	0.0606 (6)
C14	0.5225 (3)	0.7025 (4)	0.0372 (2)	0.0622 (7)
C15	0.4163 (2)	0.6834 (3)	0.1052 (2)	0.0538 (6)
C16	0.0113 (3)	0.3724 (4)	0.0851 (2)	0.0541 (6)
C17	−0.0433 (2)	0.2305 (3)	0.1448 (3)	0.0613 (7)
C18	−0.0849 (4)	0.1125 (5)	0.1895 (5)	0.1046 (14)
C19	0.2236 (3)	0.8536 (3)	0.3129 (2)	0.0504 (5)
C20	0.1674 (3)	0.8738 (4)	0.4290 (3)	0.0701 (8)
C21	0.1218 (5)	0.8918 (10)	0.5191 (5)	0.136 (2)
H5	0.189 (2)	0.328 (3)	0.420 (2)	0.051 (7)*
H6	0.228 (3)	0.296 (4)	0.632 (3)	0.068 (8)*
H7	0.389 (3)	0.445 (4)	0.763 (3)	0.080 (10)*
H8	0.522 (3)	0.636 (4)	0.669 (2)	0.059 (7)*
H9	0.486 (3)	0.677 (4)	0.455 (3)	0.075 (9)*
H11	0.562 (2)	0.435 (4)	0.323 (2)	0.054 (7)*
H12	0.736 (3)	0.474 (4)	0.203 (3)	0.069 (8)*
H13	0.720 (3)	0.641 (4)	0.027 (3)	0.068 (8)*
H14	0.511 (3)	0.777 (4)	−0.037 (3)	0.072 (8)*
H15	0.330 (3)	0.737 (4)	0.076 (3)	0.060 (7)*
H16A	−0.051 (3)	0.446 (4)	0.056 (3)	0.060 (8)*
H16B	0.053 (3)	0.332 (4)	0.014 (3)	0.070 (9)*
H18	−0.113 (6)	0.010 (8)	0.228 (6)	0.18 (2)*
H19A	0.315 (3)	0.879 (4)	0.328 (2)	0.061 (7)*
H19B	0.182 (3)	0.926 (4)	0.250 (3)	0.067 (8)*
H21	0.087 (5)	0.905 (8)	0.590 (5)	0.16 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0528 (9)	0.0399 (8)	0.0585 (10)	0.0036 (7)	0.0088 (7)	−0.0076 (7)
O2	0.0430 (8)	0.0499 (9)	0.0606 (10)	0.0084 (7)	−0.0045 (7)	0.0041 (7)
N1	0.0425 (9)	0.0389 (9)	0.0426 (9)	−0.0019 (7)	−0.0033 (7)	−0.0008 (8)
N2	0.0373 (8)	0.0349 (9)	0.0492 (10)	0.0009 (7)	0.0014 (7)	−0.0011 (7)
C1	0.0361 (9)	0.0342 (9)	0.0432 (11)	0.0012 (8)	0.0035 (8)	0.0012 (8)
C2	0.0414 (10)	0.0385 (10)	0.0368 (10)	−0.0003 (8)	0.0070 (8)	0.0009 (8)
C3	0.0396 (10)	0.0403 (11)	0.0365 (10)	0.0013 (8)	0.0024 (8)	0.0058 (8)
C4	0.0349 (9)	0.0385 (11)	0.0423 (11)	0.0052 (8)	0.0055 (8)	0.0012 (8)
C5	0.0414 (11)	0.0468 (12)	0.0501 (12)	0.0006 (9)	0.0094 (9)	0.0032 (10)
C6	0.0574 (13)	0.0592 (15)	0.0556 (14)	0.0074 (12)	0.0183 (11)	0.0142 (12)
C7	0.0644 (15)	0.0677 (16)	0.0400 (12)	0.0230 (13)	0.0082 (10)	0.0047 (11)
C8	0.0531 (12)	0.0545 (14)	0.0476 (13)	0.0104 (11)	−0.0037 (10)	−0.0093 (11)
C9	0.0438 (11)	0.0440 (11)	0.0478 (12)	0.0016 (9)	0.0035 (9)	−0.0013 (9)
C10	0.0386 (9)	0.0391 (11)	0.0412 (10)	−0.0022 (8)	0.0060 (7)	0.0009 (8)
C11	0.0405 (10)	0.0450 (12)	0.0468 (12)	0.0014 (9)	0.0054 (9)	0.0040 (10)
C12	0.0419 (11)	0.0616 (15)	0.0605 (15)	0.0032 (11)	0.0105 (10)	0.0011 (12)
C13	0.0519 (13)	0.0735 (17)	0.0601 (14)	−0.0040 (12)	0.0219 (11)	0.0055 (13)
C14	0.0692 (16)	0.0698 (17)	0.0498 (14)	−0.0003 (13)	0.0166 (12)	0.0179 (13)
C15	0.0482 (12)	0.0622 (15)	0.0507 (13)	0.0044 (11)	0.0053 (10)	0.0129 (12)
C16	0.0540 (13)	0.0525 (14)	0.0520 (14)	−0.0059 (11)	−0.0086 (11)	−0.0047 (12)
C17	0.0463 (12)	0.0490 (14)	0.088 (2)	−0.0035 (10)	0.0067 (12)	−0.0068 (13)
C18	0.081 (2)	0.066 (2)	0.174 (4)	−0.0128 (18)	0.043 (2)	0.017 (2)
C19	0.0479 (13)	0.0358 (11)	0.0664 (15)	0.0013 (9)	0.0025 (11)	−0.0020 (11)
C20	0.0587 (15)	0.0758 (19)	0.0742 (19)	0.0032 (14)	0.0024 (13)	−0.0289 (16)
C21	0.103 (3)	0.214 (6)	0.094 (3)	0.001 (4)	0.026 (2)	−0.069 (4)

Geometric parameters (Å, º)

O1—C2	1.203 (3)	C10—C11	1.388 (3)
O2—C3	1.208 (2)	C10—C15	1.390 (3)
N1—C2	1.360 (3)	C11—C12	1.391 (3)
N1—C3	1.399 (3)	C11—H11	1.00 (3)
N1—C16	1.453 (3)	C12—C13	1.377 (4)
N2—C1	1.472 (3)	C12—H12	0.94 (3)
N2—C3	1.346 (3)	C13—C14	1.366 (4)
N2—C19	1.454 (3)	C13—H13	1.01 (3)
C1—C10	1.534 (3)	C14—H14	1.00 (3)
C2—C1	1.545 (3)	C15—C14	1.390 (4)
C4—C1	1.529 (3)	C15—H15	0.99 (3)
C4—C5	1.390 (3)	C16—H16A	0.89 (3)
C4—C9	1.390 (3)	C16—H16B	0.98 (3)
C5—C6	1.389 (3)	C17—C16	1.447 (4)
C5—H5	1.02 (3)	C17—C18	1.162 (5)
C6—C7	1.370 (4)	C18—H18	0.97 (6)
C6—H6	0.90 (3)	C19—C20	1.462 (4)
C7—H7	1.01 (3)	C19—H19A	0.94 (3)
C8—C7	1.384 (4)	C19—H19B	0.95 (3)
C8—H8	0.98 (3)	C20—C21	1.148 (5)
C9—C8	1.380 (3)	C21—H21	0.90 (5)
C9—H9	0.93 (3)
O1···H16B	2.84 (2)	C20···C4	3.372 (3)
O1···H13^i	2.61 (2)	C20···C9	3.472 (3)
O1···H5	2.767 (18)	C2···H5	2.476 (18)
O1···H8^ii	2.62 (2)	C4···H11	2.679 (18)
O2···H18^iii	2.68 (5)	C6···H9^ii	2.97 (2)
O2···H19B	2.65 (2)	C6···H18^v	2.90 (4)
O2···H16A	2.50 (2)	C8···H11^vi	2.94 (2)
O2···H16B^iv	2.33 (2)	C8···H19A^ii	2.83 (2)
N2···H15	2.53 (2)	C9···H11	2.73 (2)
C4···C20	3.372 (3)	C10···H9	2.75 (2)
C9···C19	3.378 (3)	C10···H19A	2.96 (2)
C9···C11	3.138 (3)	C11···H14^i	2.94 (2)
C9···C20	3.472 (3)	C11···H9	2.79 (2)
C11···C9	3.138 (3)	C12···H14^i	2.91 (2)
C15···C19	3.450 (3)	C14···H7^vi	2.97 (2)
C19···C15	3.450 (3)	H8···H11^vi	2.53 (3)
C19···C9	3.378 (3)	H9···H11	2.58 (3)
C2—N1—C3	112.60 (17)	C8—C9—H9	121.2 (19)
C2—N1—C16	124.3 (2)	C11—C10—C1	120.65 (18)
C3—N1—C16	122.9 (2)	C11—C10—C15	118.4 (2)
C3—N2—C1	112.90 (16)	C15—C10—C1	120.64 (18)
C3—N2—C19	121.81 (18)	C10—C11—C12	120.2 (2)
C19—N2—C1	124.78 (17)	C10—C11—H11	120.6 (14)
N2—C1—C2	100.41 (15)	C12—C11—H11	119.3 (14)
N2—C1—C4	109.84 (16)	C11—C12—H12	119.8 (18)
N2—C1—C10	112.27 (16)	C13—C12—C11	120.9 (2)
C4—C1—C2	111.07 (16)	C13—C12—H12	119.3 (18)
C4—C1—C10	116.25 (15)	C12—C13—H13	119.5 (17)
C10—C1—C2	105.76 (16)	C14—C13—C12	119.3 (2)
O1—C2—N1	126.3 (2)	C14—C13—H13	121.2 (17)
O1—C2—C1	126.93 (19)	C13—C14—C15	120.6 (2)
N1—C2—C1	106.74 (16)	C13—C14—H14	121.1 (17)
O2—C3—N1	125.0 (2)	C15—C14—H14	118.2 (17)
O2—C3—N2	128.0 (2)	C10—C15—C14	120.7 (2)
N2—C3—N1	107.02 (17)	C10—C15—H15	119.9 (16)
C5—C4—C1	120.41 (18)	C14—C15—H15	119.3 (16)
C9—C4—C1	120.74 (18)	N1—C16—H16A	107.0 (19)
C9—C4—C5	118.6 (2)	N1—C16—H16B	108.8 (17)
C4—C5—H5	121.0 (14)	C17—C16—N1	113.0 (2)
C6—C5—C4	120.7 (2)	C17—C16—H16A	112.0 (18)
C6—C5—H5	118.4 (14)	C17—C16—H16B	108.8 (18)
C5—C6—H6	119 (2)	H16A—C16—H16B	107 (2)
C7—C6—C5	120.0 (2)	C18—C17—C16	177.3 (4)
C7—C6—H6	120.8 (19)	C17—C18—H18	176 (3)
C6—C7—C8	119.8 (2)	N2—C19—C20	114.0 (2)
C6—C7—H7	121.8 (18)	N2—C19—H19A	108.9 (18)
C8—C7—H7	118.3 (18)	N2—C19—H19B	104.8 (18)
C7—C8—H8	120.2 (16)	C20—C19—H19A	107.8 (16)
C9—C8—C7	120.4 (2)	C20—C19—H19B	112.0 (17)
C9—C8—H8	119.3 (16)	H19A—C19—H19B	109 (2)
C4—C9—H9	118.4 (19)	C21—C20—C19	178.8 (5)
C8—C9—C4	120.4 (2)	C20—C21—H21	179 (4)
C3—N2—C1—C4	−112.10 (13)	C2—N1—C3—N2	4.70 (16)
C19—N2—C1—C4	59.82 (18)	C16—N1—C3—N2	−170.68 (14)
C3—N2—C1—C10	116.91 (13)	C9—C4—C5—C6	0.3 (2)
C19—N2—C1—C10	−71.17 (19)	C1—C4—C5—C6	−173.66 (14)
C3—N2—C1—C2	4.97 (15)	C4—C5—C6—C7	−0.3 (3)
C19—N2—C1—C2	176.88 (13)	C5—C6—C7—C8	0.0 (3)
C9—C4—C1—N2	−87.33 (15)	C9—C8—C7—C6	0.3 (3)
C5—C4—C1—N2	86.52 (16)	C4—C9—C8—C7	−0.3 (3)
C9—C4—C1—C10	41.52 (19)	C5—C4—C9—C8	0.0 (2)
C5—C4—C1—C10	−144.63 (14)	C1—C4—C9—C8	173.96 (14)
C9—C4—C1—C2	162.49 (13)	N2—C1—C10—C11	159.40 (13)
C5—C4—C1—C2	−23.66 (18)	C4—C1—C10—C11	31.74 (19)
O1—C2—C1—N2	177.04 (14)	C2—C1—C10—C11	−92.03 (15)
N1—C2—C1—N2	−1.91 (14)	N2—C1—C10—C15	−27.33 (19)
O1—C2—C1—C4	−66.81 (19)	C4—C1—C10—C15	−154.99 (14)
N1—C2—C1—C4	114.23 (13)	C2—C1—C10—C15	81.25 (17)
O1—C2—C1—C10	60.15 (19)	C15—C10—C11—C12	0.6 (2)
N1—C2—C1—C10	−118.80 (12)	C1—C10—C11—C12	174.00 (15)
C3—N1—C2—O1	179.51 (14)	C10—C11—C12—C13	−0.2 (3)
C16—N1—C2—O1	−5.2 (2)	C11—C12—C13—C14	−0.1 (3)
C3—N1—C2—C1	−1.52 (16)	C12—C13—C14—C15	0.0 (3)
C16—N1—C2—C1	173.78 (14)	C10—C15—C14—C13	0.4 (3)
C19—N2—C3—O2	2.4 (2)	C11—C10—C15—C14	−0.7 (3)
C1—N2—C3—O2	174.63 (14)	C1—C10—C15—C14	−174.13 (17)
C19—N2—C3—N1	−178.28 (14)	C2—N1—C16—C17	69.8 (2)
C1—N2—C3—N1	−6.09 (16)	C3—N1—C16—C17	−115.34 (18)
C2—N1—C3—O2	−175.99 (14)	C3—N2—C19—C20	76.6 (2)
C16—N1—C3—O2	8.6 (2)	C1—N2—C19—C20	−94.61 (19)

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

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2^vii	0.98 (3)	2.33 (3)	3.178 (3)	144 (2)
C9—H9···Cg1^vi	0.93 (3)	2.93 (2)	3.778 (2)	152.7 (17)
C14—H14···Cg2^viii	1.00 (3)	2.87 (2)	3.762 (3)	149.6 (17)

Symmetry codes: (vi) −x+1, y+1/2, −z+1; (vii) −x, y−1/2, −z; (viii) −x+1, y+1/2, −z.