2-(4-Chloro­phen­oxy)-3-isopropyl-5,6,7,8-tetra­hydro-2-benzothieno[2,3-d]pyrimidin-4(3H)-one

In the title compound, C₁₉H₁₉ClN₂O₂S, the thio­phene and pyrimidine rings are almost coplanar. Intra­molecular C—H...O hydrogen bonds stabilize the mol­ecular structure. The crystal packing is determined by van der Waals forces. No inter­molecular hydrogen bonding inter­actions or π–π stacking inter­actions are present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.130
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT145_ALERT_4_C su on beta     Small or Missing  (x 10000) .....          0 Deg.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O1      ..       3.15 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.08

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               4119
           Count of symmetry unique reflns         2288
           Completeness (_total/calc)            180.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1831
           Fraction of Friedel pairs measured     0.800
           Are heavy atom types Z>Si present        yes

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

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

---

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 (Sheldrick, 2001).

2-(4-Chlorophenoxy)-3-isopropyl-5,6,7,8-tetrahydro-2- benzothieno[2,3-d]pyrimidin-4(3H)-one

Crystal data

C19H19ClN2O2S	F(000) = 392
Mr = 374.87	Dx = 1.373 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3917 reflections
a = 13.2129 (12) Å	θ = 2.9–26.7°
b = 5.7350 (5) Å	µ = 0.34 mm^−1
c = 13.2120 (12) Å	T = 292 K
β = 115.13°	Block, colorless
V = 906.46 (14) Å^3	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4119 independent reflections
Radiation source: fine-focus sealed tube	3396 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
Tmin = 0.905, Tmax = 0.967	k = −7→7
10551 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0799P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4119 reflections	Δρmax = 0.37 e Å^−3
228 parameters	Δρmin = −0.31 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1386 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

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.

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
C1	0.9094 (2)	0.6464 (6)	0.1226 (2)	0.0523 (7)
H1A	0.9395	0.7995	0.1202	0.063*
H1B	0.9589	0.5716	0.1919	0.063*
C2	0.9044 (3)	0.5044 (9)	0.0256 (4)	0.0891 (13)
H2A	0.8818	0.6059	−0.0391	0.107*
H2B	0.9793	0.4495	0.0422	0.107*
C3	0.8298 (3)	0.3039 (8)	−0.0047 (4)	0.0847 (11)
H3A	0.8608	0.1885	0.0542	0.102*
H3B	0.8290	0.2357	−0.0722	0.102*
C4	0.7103 (3)	0.3516 (6)	−0.0241 (3)	0.0604 (8)
H4A	0.6673	0.4019	−0.1006	0.072*
H4B	0.6767	0.2099	−0.0122	0.072*
C5	0.7079 (2)	0.5367 (5)	0.0544 (2)	0.0475 (6)
C6	0.79458 (19)	0.6719 (5)	0.11985 (18)	0.0420 (6)
C7	0.76436 (19)	0.8303 (5)	0.18677 (19)	0.0397 (5)
C8	0.65449 (19)	0.8086 (5)	0.1690 (2)	0.0432 (6)
C9	0.83424 (19)	0.9864 (5)	0.2731 (2)	0.0417 (5)
C10	0.8517 (2)	1.2344 (5)	0.4340 (2)	0.0458 (6)
H10	0.9272	1.2293	0.4375	0.055*
C11	0.8208 (3)	1.4871 (6)	0.4261 (3)	0.0692 (9)
H11A	0.8108	1.5467	0.3546	0.104*
H11B	0.8793	1.5723	0.4842	0.104*
H11C	0.7525	1.5042	0.4345	0.104*
C12	0.8599 (3)	1.1178 (6)	0.5412 (2)	0.0630 (8)
H12A	0.7868	1.1078	0.5398	0.095*
H12B	0.9078	1.2083	0.6046	0.095*
H12C	0.8904	0.9639	0.5465	0.095*
C13	0.66845 (19)	1.0596 (5)	0.3018 (2)	0.0440 (6)
C14	0.5156 (2)	1.1681 (5)	0.3403 (2)	0.0501 (6)
C15	0.4800 (3)	0.9936 (6)	0.3861 (3)	0.0679 (8)
H15	0.5298	0.8803	0.4297	0.082*
C16	0.3694 (3)	0.9854 (7)	0.3674 (3)	0.0682 (8)
H16	0.3434	0.8644	0.3968	0.082*
C17	0.2983 (2)	1.1563 (6)	0.3054 (2)	0.0554 (7)
C18	0.3355 (3)	1.3341 (7)	0.2623 (3)	0.0694 (9)
H18	0.2864	1.4509	0.2212	0.083*
C19	0.4464 (3)	1.3419 (7)	0.2795 (3)	0.0675 (8)
H19	0.4728	1.4626	0.2503	0.081*
Cl1	0.15818 (6)	1.1419 (2)	0.28112 (7)	0.0803 (3)
N1	0.77978 (15)	1.0963 (4)	0.33298 (15)	0.0421 (4)
N2	0.60311 (17)	0.9265 (4)	0.22360 (19)	0.0510 (6)
O1	0.93306 (14)	1.0255 (4)	0.29906 (17)	0.0593 (6)
O2	0.62982 (15)	1.1857 (4)	0.36468 (17)	0.0654 (6)
S1	0.58616 (5)	0.59766 (14)	0.07057 (6)	0.0566 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0428 (13)	0.0616 (18)	0.0575 (15)	0.0018 (12)	0.0261 (11)	−0.0039 (13)
C2	0.066 (2)	0.117 (3)	0.097 (3)	−0.008 (2)	0.047 (2)	−0.038 (3)
C3	0.080 (2)	0.084 (3)	0.107 (3)	−0.006 (2)	0.055 (2)	−0.037 (2)
C4	0.0651 (18)	0.0599 (18)	0.0527 (16)	0.0040 (15)	0.0217 (14)	−0.0100 (14)
C5	0.0444 (13)	0.0566 (17)	0.0403 (12)	0.0041 (11)	0.0167 (11)	−0.0017 (11)
C6	0.0409 (12)	0.0486 (14)	0.0367 (11)	0.0061 (10)	0.0168 (10)	0.0045 (10)
C7	0.0344 (11)	0.0458 (12)	0.0369 (12)	0.0021 (10)	0.0134 (9)	0.0028 (10)
C8	0.0316 (11)	0.0523 (14)	0.0419 (12)	−0.0012 (10)	0.0119 (10)	−0.0041 (11)
C9	0.0371 (12)	0.0485 (14)	0.0400 (12)	−0.0004 (10)	0.0169 (10)	0.0043 (10)
C10	0.0390 (13)	0.0468 (15)	0.0480 (14)	−0.0066 (11)	0.0152 (11)	−0.0075 (11)
C11	0.088 (2)	0.0461 (16)	0.0630 (19)	−0.0120 (16)	0.0221 (17)	−0.0005 (14)
C12	0.0809 (19)	0.0486 (16)	0.0440 (13)	0.0016 (16)	0.0114 (13)	0.0000 (13)
C13	0.0353 (12)	0.0513 (15)	0.0465 (12)	−0.0006 (11)	0.0183 (10)	−0.0037 (11)
C14	0.0384 (13)	0.0625 (17)	0.0539 (14)	−0.0035 (12)	0.0241 (11)	−0.0173 (13)
C15	0.0536 (17)	0.0626 (19)	0.086 (2)	0.0120 (15)	0.0287 (16)	0.0089 (17)
C16	0.0570 (18)	0.075 (2)	0.079 (2)	−0.0085 (17)	0.0346 (16)	0.0091 (18)
C17	0.0397 (13)	0.082 (2)	0.0489 (13)	0.0021 (14)	0.0233 (11)	−0.0099 (14)
C18	0.0528 (17)	0.073 (2)	0.078 (2)	0.0121 (16)	0.0235 (16)	0.0169 (18)
C19	0.0581 (17)	0.070 (2)	0.077 (2)	−0.0023 (16)	0.0310 (16)	0.0100 (18)
Cl1	0.0433 (4)	0.1315 (9)	0.0715 (5)	−0.0007 (5)	0.0296 (3)	−0.0147 (5)
N1	0.0333 (9)	0.0469 (11)	0.0442 (10)	−0.0011 (9)	0.0147 (8)	−0.0002 (10)
N2	0.0344 (11)	0.0621 (15)	0.0542 (13)	−0.0001 (10)	0.0166 (10)	−0.0146 (11)
O1	0.0334 (9)	0.0801 (15)	0.0671 (12)	−0.0106 (9)	0.0241 (8)	−0.0169 (10)
O2	0.0381 (9)	0.0877 (15)	0.0732 (12)	−0.0092 (10)	0.0263 (9)	−0.0346 (12)
S1	0.0366 (3)	0.0675 (5)	0.0589 (4)	−0.0046 (3)	0.0137 (3)	−0.0198 (3)

Geometric parameters (Å, º)

C1—C2	1.497 (5)	C10—C12	1.528 (4)
C1—C6	1.509 (3)	C10—H10	0.9800
C1—H1A	0.9700	C11—H11A	0.9600
C1—H1B	0.9700	C11—H11B	0.9600
C2—C3	1.455 (6)	C11—H11C	0.9600
C2—H2A	0.9700	C12—H12A	0.9600
C2—H2B	0.9700	C12—H12B	0.9600
C3—C4	1.514 (4)	C12—H12C	0.9600
C3—H3A	0.9700	C13—N2	1.280 (3)
C3—H3B	0.9700	C13—O2	1.354 (3)
C4—C5	1.494 (4)	C13—N1	1.365 (3)
C4—H4A	0.9700	C14—C15	1.353 (4)
C4—H4B	0.9700	C14—C19	1.361 (5)
C5—C6	1.349 (4)	C14—O2	1.406 (3)
C5—S1	1.745 (3)	C15—C16	1.376 (4)
C6—C7	1.437 (3)	C15—H15	0.9300
C7—C8	1.374 (3)	C16—C17	1.365 (5)
C7—C9	1.435 (4)	C16—H16	0.9300
C8—N2	1.362 (3)	C17—C18	1.357 (5)
C8—S1	1.724 (3)	C17—Cl1	1.741 (3)
C9—O1	1.222 (3)	C18—C19	1.385 (4)
C9—N1	1.423 (3)	C18—H18	0.9300
C10—N1	1.495 (3)	C19—H19	0.9300
C10—C11	1.497 (5)
C2—C1—C6	110.7 (2)	N1—C10—H10	105.9
C2—C1—H1A	109.5	C11—C10—H10	105.9
C6—C1—H1A	109.5	C12—C10—H10	105.9
C2—C1—H1B	109.5	C10—C11—H11A	109.5
C6—C1—H1B	109.5	C10—C11—H11B	109.5
H1A—C1—H1B	108.1	H11A—C11—H11B	109.5
C3—C2—C1	116.3 (3)	C10—C11—H11C	109.5
C3—C2—H2A	108.2	H11A—C11—H11C	109.5
C1—C2—H2A	108.2	H11B—C11—H11C	109.5
C3—C2—H2B	108.2	C10—C12—H12A	109.5
C1—C2—H2B	108.2	C10—C12—H12B	109.5
H2A—C2—H2B	107.4	H12A—C12—H12B	109.5
C2—C3—C4	116.1 (3)	C10—C12—H12C	109.5
C2—C3—H3A	108.3	H12A—C12—H12C	109.5
C4—C3—H3A	108.3	H12B—C12—H12C	109.5
C2—C3—H3B	108.3	N2—C13—O2	120.9 (2)
C4—C3—H3B	108.3	N2—C13—N1	127.3 (2)
H3A—C3—H3B	107.4	O2—C13—N1	111.8 (2)
C5—C4—C3	109.8 (3)	C15—C14—C19	122.1 (3)
C5—C4—H4A	109.7	C15—C14—O2	119.6 (3)
C3—C4—H4A	109.7	C19—C14—O2	118.0 (3)
C5—C4—H4B	109.7	C14—C15—C16	119.3 (3)
C3—C4—H4B	109.7	C14—C15—H15	120.3
H4A—C4—H4B	108.2	C16—C15—H15	120.3
C6—C5—C4	126.2 (2)	C17—C16—C15	119.4 (3)
C6—C5—S1	112.51 (19)	C17—C16—H16	120.3
C4—C5—S1	121.3 (2)	C15—C16—H16	120.3
C5—C6—C7	112.0 (2)	C18—C17—C16	120.8 (3)
C5—C6—C1	122.1 (2)	C18—C17—Cl1	120.3 (2)
C7—C6—C1	125.8 (2)	C16—C17—Cl1	118.9 (2)
C8—C7—C9	118.0 (2)	C17—C18—C19	120.1 (3)
C8—C7—C6	112.8 (2)	C17—C18—H18	119.9
C9—C7—C6	129.0 (2)	C19—C18—H18	119.9
N2—C8—C7	126.3 (2)	C14—C19—C18	118.2 (3)
N2—C8—S1	121.92 (17)	C14—C19—H19	120.9
C7—C8—S1	111.68 (19)	C18—C19—H19	120.9
O1—C9—N1	119.7 (2)	C13—N1—C9	119.9 (2)
O1—C9—C7	126.0 (2)	C13—N1—C10	123.09 (19)
N1—C9—C7	114.31 (19)	C9—N1—C10	116.84 (18)
N1—C10—C11	113.5 (2)	C13—N2—C8	114.0 (2)
N1—C10—C12	111.3 (2)	C13—O2—C14	117.9 (2)
C11—C10—C12	113.5 (2)	C8—S1—C5	91.02 (12)
C6—C1—C2—C3	−39.8 (5)	Cl1—C17—C18—C19	−178.4 (3)
C1—C2—C3—C4	52.9 (6)	C15—C14—C19—C18	−1.6 (5)
C2—C3—C4—C5	−35.3 (5)	O2—C14—C19—C18	−175.3 (3)
C3—C4—C5—C6	10.6 (4)	C17—C18—C19—C14	−0.2 (5)
C3—C4—C5—S1	−168.9 (3)	N2—C13—N1—C9	2.5 (4)
C4—C5—C6—C7	−179.1 (3)	O2—C13—N1—C9	−177.2 (2)
S1—C5—C6—C7	0.5 (3)	N2—C13—N1—C10	−172.8 (3)
C4—C5—C6—C1	−1.2 (4)	O2—C13—N1—C10	7.6 (3)
S1—C5—C6—C1	178.3 (2)	O1—C9—N1—C13	177.7 (2)
C2—C1—C6—C5	14.7 (4)	C7—C9—N1—C13	−3.8 (3)
C2—C1—C6—C7	−167.7 (3)	O1—C9—N1—C10	−6.8 (3)
C5—C6—C7—C8	−0.1 (3)	C7—C9—N1—C10	171.6 (2)
C1—C6—C7—C8	−177.8 (2)	C11—C10—N1—C13	−65.6 (3)
C5—C6—C7—C9	174.0 (3)	C12—C10—N1—C13	63.9 (3)
C1—C6—C7—C9	−3.8 (4)	C11—C10—N1—C9	119.0 (3)
C9—C7—C8—N2	1.9 (4)	C12—C10—N1—C9	−111.4 (3)
C6—C7—C8—N2	176.7 (2)	O2—C13—N2—C8	−179.1 (2)
C9—C7—C8—S1	−175.13 (19)	N1—C13—N2—C8	1.3 (4)
C6—C7—C8—S1	−0.4 (3)	C7—C8—N2—C13	−3.5 (4)
C8—C7—C9—O1	−179.8 (3)	S1—C8—N2—C13	173.2 (2)
C6—C7—C9—O1	6.4 (4)	N2—C13—O2—C14	−0.8 (4)
C8—C7—C9—N1	1.8 (3)	N1—C13—O2—C14	178.9 (2)
C6—C7—C9—N1	−172.0 (2)	C15—C14—O2—C13	85.6 (3)
C19—C14—C15—C16	2.5 (5)	C19—C14—O2—C13	−100.6 (3)
O2—C14—C15—C16	176.1 (3)	N2—C8—S1—C5	−176.7 (2)
C14—C15—C16—C17	−1.5 (5)	C7—C8—S1—C5	0.5 (2)
C15—C16—C17—C18	−0.2 (5)	C6—C5—S1—C8	−0.6 (2)
C15—C16—C17—Cl1	179.3 (3)	C4—C5—S1—C8	179.0 (2)
C16—C17—C18—C19	1.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1	0.98	2.20	2.720 (3)	112
C11—H11C···O2	0.96	2.35	2.876 (4)	114
C12—H12A···O2	0.96	2.40	2.969 (4)	117