(4-Oxo-3,4-dihydro­quinazolin-3-yl)methyl pyrrolidine-1-carbodithio­ate

In the mol­ecule of the title compound, C₁₄H₁₅N₃OS₃, the pyrrolidine ring has a slightly distorted envelope conform­ation. The dihydro­pyrimidine and benzene rings are coplanar, making a dihedral angle of 0.05 (3)°. In the crystal structure, intra- and inter­molecular C—H...S, C—H...O and C—H...N hydrogen bonds link the mol­ecules into chains along the c axis, and may be effective in the stabilization of the structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.135
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2     -   C10     ..       5.16 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

(4-Oxo-3,4-dihydroquinazolin-3-yl)methyl pyrrolidine-1-carbodithioate

Crystal data

C14H15N3OS2	Z = 2
Mr = 305.41	F(000) = 320
Triclinic, P1	Dx = 1.422 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6686 (5) Å	Cell parameters from 3566 reflections
b = 12.4808 (14) Å	θ = 2.9–28.1°
c = 13.4147 (15) Å	µ = 0.37 mm^−1
α = 66.185 (2)°	T = 292 K
β = 86.088 (2)°	Block, colorless
γ = 88.898 (2)°	0.30 × 0.20 × 0.20 mm
V = 713.40 (14) Å^3

Data collection

Bruker SMART 4K CCD area-detector diffractometer	3062 independent reflections
Radiation source: fine-focus sealed tube	2588 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −5→5
Tmin = 0.897, Tmax = 0.929	k = −15→15
6711 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.0593P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.135	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.30 e Å^−3
3062 reflections	Δρmin = −0.36 e Å^−3
181 parameters

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.5875 (4)	0.11844 (18)	0.03020 (16)	0.0528 (5)
H1	0.5822	0.0390	0.0753	0.063*
C2	0.7747 (5)	0.1604 (2)	−0.06103 (18)	0.0614 (5)
H2	0.8960	0.1092	−0.0779	0.074*
C3	0.7829 (5)	0.2794 (2)	−0.12819 (17)	0.0614 (5)
H3	0.9105	0.3071	−0.1897	0.074*
C4	0.6068 (5)	0.35604 (19)	−0.10525 (16)	0.0564 (5)
H4	0.6148	0.4353	−0.1509	0.068*
C5	0.0615 (4)	0.35515 (16)	0.09308 (15)	0.0489 (4)
H5	−0.0591	0.4083	0.1071	0.059*
C6	0.2024 (4)	0.15229 (14)	0.15025 (14)	0.0429 (4)
C7	0.4056 (4)	0.19558 (15)	0.05473 (13)	0.0412 (4)
C8	0.4137 (4)	0.31543 (16)	−0.01289 (14)	0.0445 (4)
C9	−0.1637 (4)	0.20483 (17)	0.26053 (14)	0.0481 (4)
H9A	−0.2856	0.1425	0.2611	0.058*
H9B	−0.2855	0.2708	0.2542	0.058*
C10	0.0456 (4)	0.28657 (14)	0.40899 (13)	0.0430 (4)
C11	0.2707 (5)	0.15274 (17)	0.57739 (16)	0.0545 (5)
H11A	0.4388	0.1252	0.5484	0.065*
H11B	0.1181	0.0948	0.5966	0.065*
C12	0.3392 (6)	0.1772 (2)	0.67513 (19)	0.0724 (7)
H12A	0.1704	0.1663	0.7247	0.087*
H12B	0.4901	0.1263	0.7144	0.087*
C13	0.4362 (6)	0.3028 (2)	0.6261 (2)	0.0694 (6)
H13A	0.6385	0.3090	0.6023	0.083*
H13B	0.4057	0.3378	0.6786	0.083*
C14	0.2566 (5)	0.36235 (17)	0.53032 (16)	0.0539 (5)
H14A	0.0865	0.3964	0.5511	0.065*
H14B	0.3654	0.4234	0.4711	0.065*
N1	0.2355 (4)	0.39546 (13)	0.00742 (12)	0.0514 (4)
N2	0.0395 (3)	0.23972 (12)	0.16565 (11)	0.0422 (3)
N3	0.1791 (3)	0.26743 (12)	0.49840 (11)	0.0444 (4)
O1	0.1713 (3)	0.05038 (11)	0.21423 (11)	0.0595 (4)
S1	0.00571 (12)	0.15533 (4)	0.38803 (3)	0.05072 (19)
S2	−0.07374 (14)	0.41657 (4)	0.32718 (4)	0.0629 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0631 (12)	0.0481 (10)	0.0483 (10)	0.0083 (9)	−0.0078 (9)	−0.0204 (8)
C2	0.0629 (13)	0.0687 (13)	0.0569 (12)	0.0120 (10)	−0.0024 (10)	−0.0307 (11)
C3	0.0603 (13)	0.0750 (14)	0.0484 (11)	−0.0060 (11)	0.0044 (9)	−0.0254 (11)
C4	0.0675 (13)	0.0515 (11)	0.0424 (10)	−0.0071 (9)	0.0002 (9)	−0.0111 (8)
C5	0.0637 (12)	0.0388 (9)	0.0423 (9)	0.0097 (8)	−0.0087 (8)	−0.0140 (7)
C6	0.0526 (10)	0.0364 (8)	0.0394 (8)	0.0008 (7)	−0.0087 (7)	−0.0141 (7)
C7	0.0482 (10)	0.0387 (8)	0.0382 (8)	0.0014 (7)	−0.0094 (7)	−0.0161 (7)
C8	0.0508 (10)	0.0423 (9)	0.0391 (9)	−0.0004 (7)	−0.0082 (7)	−0.0143 (7)
C9	0.0495 (10)	0.0491 (10)	0.0447 (9)	−0.0019 (8)	−0.0016 (8)	−0.0182 (8)
C10	0.0529 (10)	0.0345 (8)	0.0378 (8)	0.0003 (7)	0.0058 (7)	−0.0121 (7)
C11	0.0708 (13)	0.0413 (9)	0.0463 (10)	0.0099 (9)	−0.0073 (9)	−0.0122 (8)
C12	0.0982 (18)	0.0640 (13)	0.0540 (12)	0.0162 (13)	−0.0226 (12)	−0.0207 (11)
C13	0.0739 (15)	0.0740 (15)	0.0670 (14)	0.0004 (12)	−0.0147 (11)	−0.0338 (12)
C14	0.0656 (12)	0.0442 (10)	0.0537 (11)	−0.0054 (9)	−0.0003 (9)	−0.0219 (9)
N1	0.0681 (11)	0.0367 (7)	0.0426 (8)	0.0039 (7)	−0.0026 (7)	−0.0092 (6)
N2	0.0489 (8)	0.0386 (7)	0.0381 (7)	0.0037 (6)	−0.0060 (6)	−0.0141 (6)
N3	0.0580 (9)	0.0336 (7)	0.0388 (7)	0.0008 (6)	−0.0007 (6)	−0.0120 (6)
O1	0.0818 (10)	0.0354 (7)	0.0522 (8)	0.0009 (6)	0.0041 (7)	−0.0095 (6)
S1	0.0777 (4)	0.0337 (2)	0.0380 (3)	0.0009 (2)	−0.0045 (2)	−0.01160 (19)
S2	0.0979 (5)	0.0364 (3)	0.0486 (3)	0.0146 (3)	−0.0121 (3)	−0.0107 (2)

Geometric parameters (Å, º)

C1—C2	1.375 (3)	C9—H9A	0.9700
C1—C7	1.394 (2)	C9—H9B	0.9700
C1—H1	0.9300	C10—N3	1.322 (2)
C2—C3	1.391 (3)	C10—S2	1.6608 (17)
C2—H2	0.9300	C10—S1	1.7854 (17)
C3—C4	1.363 (3)	C11—N3	1.473 (2)
C3—H3	0.9300	C11—C12	1.516 (3)
C4—C8	1.401 (3)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—N1	1.287 (2)	C12—C13	1.500 (4)
C5—N2	1.376 (2)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—O1	1.218 (2)	C13—C14	1.502 (3)
C6—N2	1.393 (2)	C13—H13A	0.9700
C6—C7	1.459 (2)	C13—H13B	0.9700
C7—C8	1.401 (2)	C14—N3	1.471 (2)
C8—N1	1.386 (2)	C14—H14A	0.9700
C9—N2	1.454 (2)	C14—H14B	0.9700
C9—S1	1.8014 (18)
C2—C1—C7	119.66 (19)	N3—C11—C12	103.38 (16)
C2—C1—H1	120.2	N3—C11—H11A	111.1
C7—C1—H1	120.2	C12—C11—H11A	111.1
C1—C2—C3	120.1 (2)	N3—C11—H11B	111.1
C1—C2—H2	120.0	C12—C11—H11B	111.1
C3—C2—H2	120.0	H11A—C11—H11B	109.1
C4—C3—C2	121.00 (19)	C13—C12—C11	103.94 (18)
C4—C3—H3	119.5	C13—C12—H12A	111.0
C2—C3—H3	119.5	C11—C12—H12A	111.0
C3—C4—C8	120.04 (19)	C13—C12—H12B	111.0
C3—C4—H4	120.0	C11—C12—H12B	111.0
C8—C4—H4	120.0	H12A—C12—H12B	109.0
N1—C5—N2	125.28 (17)	C12—C13—C14	105.41 (19)
N1—C5—H5	117.4	C12—C13—H13A	110.7
N2—C5—H5	117.4	C14—C13—H13A	110.7
O1—C6—N2	120.42 (16)	C12—C13—H13B	110.7
O1—C6—C7	125.63 (16)	C14—C13—H13B	110.7
N2—C6—C7	113.94 (14)	H13A—C13—H13B	108.8
C1—C7—C8	120.31 (16)	N3—C14—C13	103.86 (16)
C1—C7—C6	120.41 (16)	N3—C14—H14A	111.0
C8—C7—C6	119.28 (15)	C13—C14—H14A	111.0
N1—C8—C4	118.58 (17)	N3—C14—H14B	111.0
N1—C8—C7	122.50 (16)	C13—C14—H14B	111.0
C4—C8—C7	118.92 (17)	H14A—C14—H14B	109.0
N2—C9—S1	113.40 (13)	C5—N1—C8	116.90 (16)
N2—C9—H9A	108.9	C5—N2—C6	122.04 (15)
S1—C9—H9A	108.9	C5—N2—C9	120.25 (15)
N2—C9—H9B	108.9	C6—N2—C9	117.69 (14)
S1—C9—H9B	108.9	C10—N3—C14	122.62 (15)
H9A—C9—H9B	107.7	C10—N3—C11	126.01 (15)
N3—C10—S2	124.05 (13)	C14—N3—C11	111.37 (15)
N3—C10—S1	111.74 (12)	C10—S1—C9	103.25 (9)
S2—C10—S1	124.21 (11)
C7—C1—C2—C3	0.2 (3)	C7—C8—N1—C5	0.9 (3)
C1—C2—C3—C4	−0.1 (3)	N1—C5—N2—C6	−2.4 (3)
C2—C3—C4—C8	0.0 (3)	N1—C5—N2—C9	179.28 (17)
C2—C1—C7—C8	−0.2 (3)	O1—C6—N2—C5	−177.72 (18)
C2—C1—C7—C6	179.01 (17)	C7—C6—N2—C5	3.2 (2)
O1—C6—C7—C1	−0.4 (3)	O1—C6—N2—C9	0.7 (2)
N2—C6—C7—C1	178.68 (15)	C7—C6—N2—C9	−178.46 (14)
O1—C6—C7—C8	178.84 (17)	S1—C9—N2—C5	−112.73 (16)
N2—C6—C7—C8	−2.1 (2)	S1—C9—N2—C6	68.86 (18)
C3—C4—C8—N1	−179.31 (18)	S2—C10—N3—C14	−5.0 (3)
C3—C4—C8—C7	0.0 (3)	S1—C10—N3—C14	175.73 (14)
C1—C7—C8—N1	179.38 (16)	S2—C10—N3—C11	175.47 (15)
C6—C7—C8—N1	0.2 (3)	S1—C10—N3—C11	−3.8 (2)
C1—C7—C8—C4	0.1 (3)	C13—C14—N3—C10	−172.47 (17)
C6—C7—C8—C4	−179.14 (16)	C13—C14—N3—C11	7.1 (2)
N3—C11—C12—C13	−30.0 (2)	C12—C11—N3—C10	−166.10 (19)
C11—C12—C13—C14	35.3 (2)	C12—C11—N3—C14	14.3 (2)
C12—C13—C14—N3	−26.2 (2)	N3—C10—S1—C9	−177.50 (13)
N2—C5—N1—C8	0.2 (3)	S2—C10—S1—C9	3.24 (14)
C4—C8—N1—C5	−179.82 (17)	N2—C9—S1—C10	89.77 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···S2	0.97	2.62	3.156 (2)	115
C12—H12B···O1^i	0.97	2.58	3.507 (3)	161
C5—H5···N1^ii	0.93	2.47	3.183 (2)	134

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z.