4-Furoyl-2,3,4,5,6,7-hexa­hydro-r-2,c-7-di­phenyl-1H-1,4-diazepin-5-one: supramolecular aggregation through C—H...O interactions

In the title compound, C₂₂H₂₀N₂O₃, the phenyl substituents adopt equatorial orientations. The seven-membered heterocyclic ring adopts a distorted chair conformation. In the solid state, the symmetry-related mol­ecules are linked by intermolecular C—H...O hydrogen bonds to form a supramol­ecular aggregation.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.096
• Data-to-parameter ratio = 6.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N1     -   H1     ...          ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.01
         From the CIF: _reflns_number_total               1730
         Count of symmetry unique reflns         1733
         Completeness (_total/calc)             99.83%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

4-Furoyl-2,3,4,5,6,7-hexahydro-r-2,c-7-diphenyl-1H-1,4-diazepin-5-one

Crystal data

C22H20N2O3	Dx = 1.296 Mg m^−3
Mr = 360.40	Melting point: 401 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
a = 8.9941 (2) Å	Cell parameters from 1904 reflections
b = 19.8913 (4) Å	θ = 2.0–25.0°
c = 10.3244 (2) Å	µ = 0.09 mm^−1
V = 1847.08 (7) Å^3	T = 160 K
Z = 4	Prism, colourless
F(000) = 760	0.30 × 0.18 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	1538 reflections with I > 2σ(I)
Radiation source: Nonius FR591 sealed tube generator	Rint = 0.065
Horizontally mounted graphite crystal monochromator	θmax = 25.0°, θmin = 2.5°
Detector resolution: 9 pixels mm^-1	h = −10→10
φ and ω scans with κ offsets	k = −23→23
24574 measured reflections	l = −12→12
1730 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom & difmap
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0606P)^2 + 0.2477P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1728 reflections	Δρmax = 0.14 e Å^−3
249 parameters	Δρmin = −0.17 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (5)

Special details

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.908 (1) Frames collected: 856 Seconds exposure per frame: 75 Degrees rotation per frame: 0.5 Crystal-Detector distance (mm): 30.0

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O5	0.9796 (2)	0.26276 (9)	0.8438 (2)	0.0477 (5)
O8	0.8531 (2)	0.37184 (10)	0.5655 (2)	0.0519 (6)
O10	0.7606 (2)	0.36455 (11)	0.8948 (2)	0.0543 (6)
N1	0.8132 (2)	0.12648 (11)	0.5617 (2)	0.0355 (5)
H1	0.853 (3)	0.0939 (16)	0.503 (4)	0.050 (8)*
N4	0.8088 (2)	0.27632 (10)	0.6832 (2)	0.0384 (5)
C2	0.8124 (3)	0.19199 (12)	0.4973 (3)	0.0348 (6)
H2	0.9173	0.2078	0.4871	0.042*
C3	0.7255 (3)	0.24395 (13)	0.5771 (3)	0.0386 (6)
H31	0.6894	0.2795	0.5177	0.046*
H32	0.6371	0.2215	0.6145	0.046*
C5	0.8805 (3)	0.23864 (13)	0.7782 (3)	0.0390 (6)
C6	0.8349 (3)	0.16612 (13)	0.7890 (3)	0.0413 (6)
H61	0.7251	0.1631	0.7848	0.050*
H62	0.8669	0.1484	0.8741	0.050*
C7	0.9022 (3)	0.12241 (13)	0.6812 (3)	0.0348 (6)
H7	1.0046	0.1393	0.6621	0.042*
C8	0.8375 (3)	0.34583 (13)	0.6712 (3)	0.0399 (6)
C9	0.8363 (3)	0.38553 (14)	0.7894 (3)	0.0409 (6)
C11	0.7730 (4)	0.4162 (2)	0.9835 (3)	0.0665 (10)
H11	0.7288	0.4160	1.0671	0.080*
C12	0.8536 (5)	0.46537 (17)	0.9373 (4)	0.0719 (11)
H12	0.8798	0.5057	0.9810	0.086*
C13	0.8947 (4)	0.44694 (14)	0.8091 (4)	0.0547 (8)
H13	0.9516	0.4727	0.7495	0.066*
C14	0.7424 (3)	0.18561 (12)	0.3647 (3)	0.0361 (6)
C15	0.7968 (4)	0.22333 (14)	0.2625 (3)	0.0478 (7)
H15	0.8785	0.2528	0.2761	0.057*
C16	0.7331 (4)	0.21858 (16)	0.1398 (3)	0.0563 (9)
H16	0.7712	0.2448	0.0705	0.068*
C17	0.6141 (4)	0.17559 (15)	0.1189 (3)	0.0519 (8)
H17	0.5714	0.1718	0.0350	0.062*
C18	0.5584 (3)	0.13852 (15)	0.2199 (3)	0.0463 (7)
H18	0.4767	0.1092	0.2058	0.056*
C19	0.6206 (3)	0.14345 (14)	0.3428 (3)	0.0407 (6)
H19	0.5801	0.1180	0.4122	0.049*
C20	0.9130 (3)	0.04858 (13)	0.7207 (3)	0.0382 (6)
C21	1.0312 (3)	0.01038 (13)	0.6776 (3)	0.0437 (6)
H21	1.1060	0.0305	0.6255	0.052*
C22	1.0417 (3)	−0.05721 (14)	0.7099 (4)	0.0547 (8)
H22	1.1235	−0.0830	0.6797	0.066*
C23	0.9340 (4)	−0.08695 (15)	0.7854 (4)	0.0558 (8)
H23	0.9413	−0.1332	0.8074	0.067*
C24	0.8156 (4)	−0.04912 (16)	0.8288 (3)	0.0546 (8)
H24	0.7410	−0.0694	0.8809	0.066*
C25	0.8048 (3)	0.01822 (15)	0.7970 (3)	0.0486 (7)
H25	0.7229	0.0439	0.8274	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0533 (11)	0.0496 (10)	0.0403 (11)	0.0049 (9)	−0.0099 (10)	−0.0068 (10)
O8	0.0660 (13)	0.0549 (12)	0.0347 (12)	0.0078 (10)	0.0038 (11)	0.0043 (10)
O10	0.0588 (12)	0.0642 (13)	0.0399 (13)	0.0016 (10)	0.0034 (10)	−0.0047 (11)
N1	0.0402 (11)	0.0386 (11)	0.0277 (12)	0.0031 (9)	−0.0001 (10)	0.0002 (10)
N4	0.0440 (11)	0.0402 (11)	0.0309 (12)	0.0047 (9)	−0.0037 (10)	−0.0045 (10)
C2	0.0382 (13)	0.0360 (13)	0.0303 (14)	0.0032 (11)	0.0005 (11)	−0.0003 (11)
C3	0.0378 (13)	0.0447 (14)	0.0333 (14)	0.0074 (11)	−0.0038 (11)	−0.0056 (12)
C5	0.0447 (14)	0.0457 (15)	0.0267 (13)	0.0065 (12)	−0.0002 (13)	−0.0035 (12)
C6	0.0466 (15)	0.0462 (15)	0.0311 (14)	0.0013 (12)	−0.0009 (12)	−0.0011 (13)
C7	0.0345 (12)	0.0401 (13)	0.0299 (13)	−0.0005 (10)	0.0000 (12)	0.0005 (11)
C8	0.0391 (13)	0.0446 (14)	0.0361 (16)	0.0095 (11)	0.0010 (13)	−0.0017 (13)
C9	0.0446 (15)	0.0464 (15)	0.0318 (14)	0.0090 (12)	−0.0025 (12)	−0.0007 (13)
C11	0.075 (2)	0.086 (3)	0.0388 (18)	0.026 (2)	−0.0037 (17)	−0.0233 (19)
C12	0.104 (3)	0.0423 (17)	0.070 (2)	0.0122 (19)	−0.028 (2)	−0.0179 (18)
C13	0.0660 (19)	0.0416 (15)	0.057 (2)	−0.0065 (14)	−0.0106 (16)	0.0040 (15)
C14	0.0429 (13)	0.0341 (13)	0.0314 (14)	0.0079 (11)	0.0016 (11)	0.0001 (11)
C15	0.0701 (19)	0.0398 (14)	0.0334 (16)	−0.0074 (13)	0.0051 (14)	0.0016 (12)
C16	0.091 (2)	0.0456 (16)	0.0320 (16)	−0.0003 (16)	0.0019 (16)	0.0074 (13)
C17	0.073 (2)	0.0525 (16)	0.0306 (15)	0.0164 (15)	−0.0078 (15)	−0.0029 (13)
C18	0.0498 (16)	0.0507 (16)	0.0383 (17)	0.0050 (13)	−0.0064 (13)	−0.0033 (13)
C19	0.0418 (14)	0.0463 (14)	0.0341 (15)	0.0025 (12)	−0.0012 (12)	0.0023 (12)
C20	0.0385 (13)	0.0450 (15)	0.0310 (14)	−0.0044 (11)	−0.0060 (11)	0.0025 (11)
C21	0.0388 (14)	0.0453 (14)	0.0468 (16)	−0.0016 (11)	−0.0030 (14)	0.0041 (13)
C22	0.0499 (15)	0.0441 (15)	0.070 (2)	0.0014 (13)	−0.0106 (16)	0.0085 (16)
C23	0.0624 (18)	0.0464 (16)	0.0584 (19)	−0.0053 (14)	−0.0179 (17)	0.0146 (16)
C24	0.0643 (18)	0.0612 (19)	0.0383 (17)	−0.0191 (16)	−0.0047 (15)	0.0124 (15)
C25	0.0498 (16)	0.0524 (16)	0.0435 (17)	−0.0065 (13)	0.0015 (14)	0.0056 (14)

Geometric parameters (Å, º)

O5—C5	1.218 (3)	C12—C13	1.423 (6)
O8—C8	1.216 (4)	C12—H12	0.9500
O10—C9	1.350 (4)	C13—H13	0.9500
O10—C11	1.382 (4)	C14—C15	1.384 (4)
N1—C2	1.463 (3)	C14—C19	1.398 (4)
N1—C7	1.474 (3)	C15—C16	1.393 (5)
N1—H1	0.96 (3)	C15—H15	0.9500
N4—C5	1.393 (4)	C16—C17	1.387 (5)
N4—C8	1.412 (3)	C16—H16	0.9500
N4—C3	1.475 (3)	C17—C18	1.372 (5)
C2—C14	1.512 (4)	C17—H17	0.9500
C2—C3	1.536 (4)	C18—C19	1.389 (4)
C2—H2	1.0000	C18—H18	0.9500
C3—H31	0.9900	C19—H19	0.9500
C3—H32	0.9900	C20—C21	1.380 (4)
C5—C6	1.504 (4)	C20—C25	1.390 (4)
C6—C7	1.536 (4)	C21—C22	1.388 (4)
C6—H61	0.9900	C21—H21	0.9500
C6—H62	0.9900	C22—C23	1.377 (5)
C7—C20	1.527 (4)	C22—H22	0.9500
C7—H7	1.0000	C23—C24	1.379 (5)
C8—C9	1.454 (4)	C23—H23	0.9500
C9—C13	1.345 (4)	C24—C25	1.383 (4)
C11—C12	1.307 (6)	C24—H24	0.9500
C11—H11	0.9500	C25—H25	0.9500
C9—O10—C11	105.3 (3)	C11—C12—C13	106.9 (3)
C2—N1—C7	115.6 (2)	C11—C12—H12	126.5
C2—N1—H1	108.5 (19)	C13—C12—H12	126.5
C7—N1—H1	106.9 (19)	C9—C13—C12	105.8 (3)
C5—N4—C8	120.3 (2)	C9—C13—H13	127.1
C5—N4—C3	121.6 (2)	C12—C13—H13	127.1
C8—N4—C3	117.1 (2)	C15—C14—C19	118.6 (3)
N1—C2—C14	109.8 (2)	C15—C14—C2	119.8 (2)
N1—C2—C3	111.0 (2)	C19—C14—C2	121.5 (3)
C14—C2—C3	109.3 (2)	C14—C15—C16	120.7 (3)
N1—C2—H2	108.9	C14—C15—H15	119.6
C14—C2—H2	108.9	C16—C15—H15	119.6
C3—C2—H2	108.9	C17—C16—C15	120.1 (3)
N4—C3—C2	115.7 (2)	C17—C16—H16	120.0
N4—C3—H31	108.4	C15—C16—H16	120.0
C2—C3—H31	108.4	C18—C17—C16	119.6 (3)
N4—C3—H32	108.4	C18—C17—H17	120.2
C2—C3—H32	108.4	C16—C17—H17	120.2
H31—C3—H32	107.4	C17—C18—C19	120.6 (3)
O5—C5—N4	121.2 (2)	C17—C18—H18	119.7
O5—C5—C6	122.4 (3)	C19—C18—H18	119.7
N4—C5—C6	116.2 (2)	C18—C19—C14	120.4 (3)
C5—C6—C7	112.5 (2)	C18—C19—H19	119.8
C5—C6—H61	109.1	C14—C19—H19	119.8
C7—C6—H61	109.1	C21—C20—C25	118.8 (3)
C5—C6—H62	109.1	C21—C20—C7	119.5 (2)
C7—C6—H62	109.1	C25—C20—C7	121.6 (2)
H61—C6—H62	107.8	C20—C21—C22	120.6 (3)
N1—C7—C20	108.1 (2)	C20—C21—H21	119.7
N1—C7—C6	111.2 (2)	C22—C21—H21	119.7
C20—C7—C6	112.1 (2)	C23—C22—C21	120.3 (3)
N1—C7—H7	108.5	C23—C22—H22	119.9
C20—C7—H7	108.5	C21—C22—H22	119.9
C6—C7—H7	108.5	C22—C23—C24	119.5 (3)
O8—C8—N4	121.1 (3)	C22—C23—H23	120.2
O8—C8—C9	121.6 (2)	C24—C23—H23	120.2
N4—C8—C9	117.2 (3)	C23—C24—C25	120.4 (3)
C13—C9—O10	110.9 (3)	C23—C24—H24	119.8
C13—C9—C8	128.1 (3)	C25—C24—H24	119.8
O10—C9—C8	120.8 (2)	C24—C25—C20	120.4 (3)
C12—C11—O10	111.0 (3)	C24—C25—H25	119.8
C12—C11—H11	124.5	C20—C25—H25	119.8
O10—C11—H11	124.5
C7—N1—C2—C14	169.3 (2)	O10—C9—C13—C12	0.7 (3)
C7—N1—C2—C3	−69.8 (3)	C8—C9—C13—C12	175.6 (3)
C5—N4—C3—C2	−54.4 (3)	C11—C12—C13—C9	−1.5 (4)
C8—N4—C3—C2	113.6 (3)	N1—C2—C14—C15	−143.8 (2)
N1—C2—C3—N4	82.7 (3)	C3—C2—C14—C15	94.2 (3)
C14—C2—C3—N4	−156.0 (2)	N1—C2—C14—C19	37.7 (3)
C8—N4—C5—O5	−7.6 (4)	C3—C2—C14—C19	−84.2 (3)
C3—N4—C5—O5	160.1 (3)	C19—C14—C15—C16	−1.0 (4)
C8—N4—C5—C6	176.1 (2)	C2—C14—C15—C16	−179.5 (3)
C3—N4—C5—C6	−16.3 (4)	C14—C15—C16—C17	−0.2 (5)
O5—C5—C6—C7	−99.7 (3)	C15—C16—C17—C18	0.8 (5)
N4—C5—C6—C7	76.6 (3)	C16—C17—C18—C19	−0.3 (5)
C2—N1—C7—C20	−169.9 (2)	C17—C18—C19—C14	−1.0 (4)
C2—N1—C7—C6	66.7 (3)	C15—C14—C19—C18	1.6 (4)
C5—C6—C7—N1	−83.0 (3)	C2—C14—C19—C18	−180.0 (3)
C5—C6—C7—C20	155.8 (2)	N1—C7—C20—C21	91.8 (3)
C5—N4—C8—O8	137.8 (3)	C6—C7—C20—C21	−145.3 (3)
C3—N4—C8—O8	−30.4 (4)	N1—C7—C20—C25	−86.8 (3)
C5—N4—C8—C9	−46.8 (3)	C6—C7—C20—C25	36.1 (3)
C3—N4—C8—C9	145.0 (2)	C25—C20—C21—C22	0.1 (4)
C11—O10—C9—C13	0.2 (3)	C7—C20—C21—C22	−178.6 (3)
C11—O10—C9—C8	−175.1 (3)	C20—C21—C22—C23	0.0 (5)
O8—C8—C9—C13	−22.6 (4)	C21—C22—C23—C24	0.0 (5)
N4—C8—C9—C13	162.0 (3)	C22—C23—C24—C25	0.0 (5)
O8—C8—C9—O10	151.8 (3)	C23—C24—C25—C20	0.1 (5)
N4—C8—C9—O10	−23.6 (4)	C21—C20—C25—C24	−0.1 (4)
C9—O10—C11—C12	−1.2 (4)	C7—C20—C25—C24	178.5 (3)
O10—C11—C12—C13	1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O5^i	0.95	2.50	3.322 (4)	144
C19—H19···O8^ii	0.95	2.59	3.342 (4)	136
C24—H24···O8^iii	0.95	2.39	3.278 (4)	155
C11—H11···Cg3^iv	0.95	2.69	3.538 (4)	149
C15—H15···Cg2^v	0.95	3.02	3.925 (4)	160
C17—H17···Cg1^i	0.95	3.24	4.008 (4)	140
C22—H22···Cg2^vi	0.95	2.72	3.540 (3)	145

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