3,5-Dichloro-6-morpholinopyridin-2-yl diethyl thio­phosphate

In the title compound, C₁₃H₁₉Cl₂N₂O₄PS, the morpholine ring adopts a chair conformation. The P=S bond distance is 1.9050 (8) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.113
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3,5-Dichloro-6-morpholinopyridin-2-yl diethyl thiophosphate

Crystal data

C13H19Cl2N2O4PS	Z = 2
Mr = 401.24	F(000) = 416.0
Triclinic, P1	Dx = 1.433 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.771 (4) Å	Cell parameters from 7625 reflections
b = 10.464 (7) Å	θ = 3.2–27.5°
c = 12.063 (5) Å	µ = 0.57 mm^−1
α = 88.23 (2)°	T = 298 K
β = 72.106 (17)°	Chunk, colorless
γ = 84.80 (2)°	0.38 × 0.30 × 0.28 mm
V = 929.6 (9) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3117 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→8
Tmin = 0.812, Tmax = 0.854	k = −13→13
9238 measured reflections	l = −15→15
4219 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0011Fo^2 + 1.04σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 0.113	Δρmax = 0.38 e Å^−3
S = 1.00	Δρmin = −0.32 e Å^−3
4219 reflections	Extinction correction: Larson (1970), equation 22
209 parameters	Extinction coefficient: 65 (13)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl1	0.66222 (8)	0.57954 (6)	0.65607 (6)	0.06994 (18)
Cl2	0.44563 (8)	0.14733 (5)	0.53694 (5)	0.06651 (16)
S1	0.04992 (9)	0.74212 (6)	0.68000 (5)	0.06552 (18)
P1	0.11265 (6)	0.71587 (5)	0.82025 (4)	0.04709 (14)
O1	0.2819 (2)	0.61190 (13)	0.80940 (12)	0.0585 (4)
O2	−0.0371 (2)	0.67656 (17)	0.93118 (12)	0.0682 (4)
O3	0.1772 (2)	0.83016 (13)	0.87231 (12)	0.0613 (4)
O4	−0.2537 (2)	0.13964 (17)	0.72734 (13)	0.0686 (5)
N1	0.1873 (2)	0.43164 (14)	0.75066 (12)	0.0464 (4)
N2	0.0781 (2)	0.24549 (14)	0.70291 (12)	0.0448 (4)
C1	0.3197 (2)	0.50538 (18)	0.73917 (16)	0.0467 (5)
C2	0.4935 (2)	0.48023 (19)	0.66425 (17)	0.0490 (5)
C3	0.5290 (2)	0.37031 (19)	0.59869 (17)	0.0516 (5)
C4	0.3928 (2)	0.29092 (18)	0.61110 (16)	0.0464 (5)
C5	0.2189 (2)	0.32396 (17)	0.68670 (14)	0.0420 (4)
C6	0.0154 (2)	0.2272 (2)	0.60143 (17)	0.0511 (5)
C7	−0.1047 (2)	0.1183 (2)	0.62561 (19)	0.0599 (6)
C8	−0.1902 (3)	0.1549 (2)	0.82463 (19)	0.0650 (6)
C9	−0.0780 (2)	0.2684 (2)	0.80765 (17)	0.0559 (5)
C10	−0.1838 (3)	0.6025 (2)	0.9325 (2)	0.0682 (7)
C11	−0.3561 (4)	0.6739 (3)	0.9872 (3)	0.1164 (13)
C12	0.3114 (4)	0.9096 (2)	0.7987 (2)	0.0825 (8)
C13	0.3333 (4)	1.0164 (2)	0.8647 (2)	0.0973 (11)
H3	0.6438	0.3499	0.5466	0.062*
H61	−0.0524	0.3051	0.5872	0.061*
H62	0.1192	0.2074	0.5334	0.061*
H71	−0.0339	0.0399	0.6354	0.072*
H72	−0.1499	0.1091	0.5600	0.072*
H81	−0.1163	0.0779	0.8338	0.078*
H82	−0.2935	0.1681	0.8942	0.078*
H91	−0.0363	0.2775	0.8748	0.067*
H92	−0.1503	0.3460	0.7979	0.067*
H101	−0.1760	0.5821	0.8531	0.082*
H102	−0.1753	0.5236	0.9757	0.082*
H111	−0.3671	0.7503	0.9429	0.140*
H112	−0.3624	0.6968	1.0649	0.140*
H113	−0.4530	0.6219	0.9901	0.140*
H121	0.4266	0.8586	0.7697	0.099*
H122	0.2716	0.9418	0.7335	0.099*
H131	0.4138	1.0726	0.8138	0.117*
H132	0.3833	0.9851	0.9249	0.117*
H133	0.2174	1.0626	0.8992	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0664 (3)	0.0668 (3)	0.0866 (4)	−0.0279 (2)	−0.0330 (3)	0.0116 (2)
Cl2	0.0669 (3)	0.0470 (3)	0.0773 (3)	0.0043 (2)	−0.0108 (2)	−0.0166 (2)
S1	0.0890 (4)	0.0617 (3)	0.0523 (2)	−0.0089 (2)	−0.0311 (2)	0.0070 (2)
P1	0.0612 (3)	0.0403 (2)	0.0406 (2)	−0.0127 (2)	−0.0143 (2)	−0.00150 (19)
O1	0.0709 (9)	0.0487 (8)	0.0661 (8)	−0.0052 (7)	−0.0347 (7)	−0.0123 (6)
O2	0.0728 (10)	0.0883 (12)	0.0442 (7)	−0.0351 (8)	−0.0111 (7)	−0.0008 (7)
O3	0.0826 (10)	0.0467 (8)	0.0531 (7)	−0.0238 (7)	−0.0129 (7)	−0.0078 (6)
O4	0.0557 (8)	0.0763 (11)	0.0763 (9)	−0.0198 (7)	−0.0191 (7)	−0.0074 (8)
N1	0.0519 (9)	0.0428 (8)	0.0473 (8)	−0.0044 (7)	−0.0186 (7)	−0.0046 (6)
N2	0.0489 (8)	0.0455 (9)	0.0415 (7)	−0.0093 (6)	−0.0143 (6)	−0.0035 (6)
C1	0.0579 (11)	0.0399 (10)	0.0497 (9)	−0.0065 (8)	−0.0268 (9)	0.0000 (7)
C2	0.0511 (11)	0.0460 (11)	0.0566 (10)	−0.0132 (8)	−0.0248 (9)	0.0095 (8)
C3	0.0472 (10)	0.0512 (11)	0.0541 (10)	−0.0018 (8)	−0.0136 (9)	0.0048 (9)
C4	0.0512 (10)	0.0390 (10)	0.0491 (9)	−0.0003 (8)	−0.0164 (8)	−0.0026 (7)
C5	0.0498 (10)	0.0372 (9)	0.0409 (8)	−0.0040 (7)	−0.0166 (7)	0.0009 (7)
C6	0.0582 (11)	0.0497 (11)	0.0501 (10)	−0.0065 (9)	−0.0227 (9)	−0.0029 (8)
C7	0.0647 (13)	0.0582 (13)	0.0622 (11)	−0.0137 (10)	−0.0244 (11)	−0.0082 (10)
C8	0.0580 (13)	0.0732 (16)	0.0585 (11)	−0.0183 (11)	−0.0062 (10)	−0.0011 (11)
C9	0.0516 (11)	0.0625 (13)	0.0503 (10)	−0.0112 (9)	−0.0079 (8)	−0.0107 (9)
C10	0.0678 (14)	0.0644 (15)	0.0679 (13)	−0.0168 (11)	−0.0103 (11)	−0.0086 (11)
C11	0.077 (2)	0.133 (3)	0.133 (2)	0.009 (2)	−0.0255 (19)	−0.043 (2)
C12	0.100 (2)	0.0685 (16)	0.0775 (15)	−0.0408 (15)	−0.0151 (14)	−0.0010 (13)
C13	0.124 (2)	0.0782 (19)	0.103 (2)	−0.0552 (18)	−0.0431 (19)	0.0115 (16)

Geometric parameters (Å, º)

Cl1—C2	1.724 (2)	C10—C11	1.446 (3)
Cl2—C4	1.7238 (19)	C12—C13	1.444 (4)
S1—P1	1.9050 (8)	C3—H3	0.930
P1—O1	1.6043 (15)	C6—H61	0.970
P1—O2	1.5523 (14)	C6—H62	0.970
P1—O3	1.5570 (17)	C7—H71	0.970
O1—C1	1.376 (2)	C7—H72	0.970
O2—C10	1.432 (3)	C8—H81	0.970
O3—C12	1.453 (3)	C8—H82	0.970
O4—C7	1.412 (2)	C9—H91	0.970
O4—C8	1.424 (3)	C9—H92	0.970
N1—C1	1.312 (2)	C10—H101	0.970
N1—C5	1.346 (2)	C10—H102	0.970
N2—C5	1.390 (2)	C11—H111	0.960
N2—C6	1.473 (2)	C11—H112	0.960
N2—C9	1.466 (2)	C11—H113	0.960
C1—C2	1.382 (2)	C12—H121	0.970
C2—C3	1.374 (2)	C12—H122	0.970
C3—C4	1.374 (2)	C13—H131	0.960
C4—C5	1.398 (2)	C13—H132	0.960
C6—C7	1.503 (3)	C13—H133	0.960
C8—C9	1.509 (3)
S1—P1—O1	114.06 (6)	H61—C6—H62	109.5
S1—P1—O2	117.89 (7)	O4—C7—H71	108.9
S1—P1—O3	118.83 (6)	O4—C7—H72	108.9
O1—P1—O2	105.08 (8)	C6—C7—H71	108.9
O1—P1—O3	99.75 (9)	C6—C7—H72	108.9
O2—P1—O3	98.49 (8)	H71—C7—H72	109.5
P1—O1—C1	123.76 (15)	O4—C8—H81	109.1
P1—O2—C10	125.30 (14)	O4—C8—H82	109.1
P1—O3—C12	120.80 (14)	C9—C8—H81	109.1
C7—O4—C8	109.78 (17)	C9—C8—H82	109.1
C1—N1—C5	119.35 (14)	H81—C8—H82	109.5
C5—N2—C6	116.66 (14)	N2—C9—H91	109.8
C5—N2—C9	116.70 (15)	N2—C9—H92	109.8
C6—N2—C9	110.04 (16)	C8—C9—H91	109.8
O1—C1—N1	117.00 (15)	C8—C9—H92	109.8
O1—C1—C2	118.83 (18)	H91—C9—H92	109.5
N1—C1—C2	124.14 (17)	O2—C10—H101	109.2
Cl1—C2—C1	121.64 (15)	O2—C10—H102	109.2
Cl1—C2—C3	120.84 (14)	C11—C10—H101	109.2
C1—C2—C3	117.48 (19)	C11—C10—H102	109.2
C2—C3—C4	119.12 (16)	H101—C10—H102	109.5
Cl2—C4—C3	118.18 (13)	C10—C11—H111	109.5
Cl2—C4—C5	121.48 (15)	C10—C11—H112	109.5
C3—C4—C5	120.27 (17)	C10—C11—H113	109.5
N1—C5—N2	118.28 (14)	H111—C11—H112	109.5
N1—C5—C4	119.60 (17)	H111—C11—H113	109.5
N2—C5—C4	122.04 (16)	H112—C11—H113	109.5
N2—C6—C7	109.28 (16)	O3—C12—H121	109.3
O4—C7—C6	111.78 (18)	O3—C12—H122	109.3
O4—C8—C9	111.01 (18)	C13—C12—H121	109.3
N2—C9—C8	107.99 (17)	C13—C12—H122	109.3
O2—C10—C11	110.4 (2)	H121—C12—H122	109.5
O3—C12—C13	110.0 (2)	C12—C13—H131	109.5
C2—C3—H3	120.4	C12—C13—H132	109.5
C4—C3—H3	120.4	C12—C13—H133	109.5
N2—C6—H61	109.5	H131—C13—H132	109.5
N2—C6—H62	109.5	H131—C13—H133	109.5
C7—C6—H61	109.5	H132—C13—H133	109.5
C7—C6—H62	109.5
S1—P1—O1—C1	−33.46 (15)	C6—N2—C5—C4	−65.3 (2)
S1—P1—O2—C10	30.8 (2)	C5—N2—C9—C8	−165.87 (18)
S1—P1—O3—C12	−46.4 (2)	C9—N2—C5—N1	−14.9 (2)
O1—P1—O2—C10	−97.56 (19)	C9—N2—C5—C4	161.74 (18)
O2—P1—O1—C1	97.14 (15)	C6—N2—C9—C8	58.2 (2)
O1—P1—O3—C12	78.08 (19)	C9—N2—C6—C7	−56.9 (2)
O3—P1—O1—C1	−161.24 (13)	O1—C1—C2—Cl1	−0.6 (2)
O2—P1—O3—C12	−174.91 (19)	O1—C1—C2—C3	177.37 (19)
O3—P1—O2—C10	159.88 (18)	N1—C1—C2—Cl1	−178.49 (16)
P1—O1—C1—N1	−52.1 (2)	N1—C1—C2—C3	−0.5 (3)
P1—O1—C1—C2	129.81 (18)	Cl1—C2—C3—C4	177.39 (16)
P1—O2—C10—C11	−121.2 (2)	C1—C2—C3—C4	−0.6 (3)
P1—O3—C12—C13	173.8 (2)	C2—C3—C4—Cl2	−174.76 (16)
C7—O4—C8—C9	60.7 (2)	C2—C3—C4—C5	2.1 (3)
C8—O4—C7—C6	−58.9 (2)	Cl2—C4—C5—N1	174.20 (15)
C1—N1—C5—N2	178.12 (17)	Cl2—C4—C5—N2	−2.4 (2)
C1—N1—C5—C4	1.4 (2)	C3—C4—C5—N1	−2.5 (3)
C5—N1—C1—O1	−177.84 (17)	C3—C4—C5—N2	−179.10 (18)
C5—N1—C1—C2	0.1 (2)	N2—C6—C7—O4	57.1 (2)
C5—N2—C6—C7	167.21 (15)	O4—C8—C9—N2	−60.4 (2)
C6—N2—C5—N1	118.09 (18)