Ethyl 2-amino-4-(4-chloro­phen­yl)-6-methyl­pyrimidine-5-carboxyl­ate

In the title compound, C₁₄H₁₄ClN₃O₂, the pyrimidine ring is twisted with respect to the benzene ring, making a dihedral angle of 42.77 (5)°. The crystal packing is stabilized by N—H...O, N—H...N and C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.031
• wR factor = 0.090
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C14H14ClN3O2	F(000) = 608
Mr = 291.73	Dx = 1.416 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12101 reflections
a = 9.1751 (2) Å	θ = 3.1–27.5°
b = 9.2232 (2) Å	µ = 0.28 mm^−1
c = 16.2613 (3) Å	T = 153 K
β = 96.223 (1)°	Block, colourless
V = 1367.98 (5) Å^3	0.50 × 0.44 × 0.27 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2916 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.016
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω scans	h = −11→11
13106 measured reflections	k = −11→11
3118 independent reflections	l = −20→21

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.639P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
3118 reflections	Δρmax = 0.35 e Å^−3
192 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0099 (17)

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
Cl	0.96445 (3)	0.56130 (4)	0.594010 (19)	0.03022 (12)
O1	0.48770 (9)	0.28768 (9)	0.75532 (5)	0.02119 (19)
O2	0.28390 (10)	0.41609 (11)	0.77055 (5)	0.0281 (2)
N1	0.33901 (10)	0.19080 (10)	0.51325 (6)	0.0180 (2)
N2	0.11347 (10)	0.13062 (11)	0.56816 (6)	0.0197 (2)
N3	0.16205 (12)	0.05230 (12)	0.43972 (6)	0.0228 (2)
C1	0.64235 (12)	0.26975 (13)	0.55261 (7)	0.0193 (2)
H1	0.6295	0.1752	0.5298	0.023*
C2	0.77822 (12)	0.33747 (13)	0.55462 (7)	0.0214 (2)
H2	0.8586	0.2895	0.5342	0.026*
C3	0.79400 (13)	0.47664 (13)	0.58708 (7)	0.0206 (2)
C4	0.67742 (13)	0.54953 (12)	0.61580 (7)	0.0207 (2)
H4	0.6895	0.6457	0.6364	0.025*
C5	0.54312 (13)	0.48033 (13)	0.61405 (7)	0.0198 (2)
H5	0.4627	0.5294	0.6337	0.024*
C6	0.52483 (12)	0.33918 (12)	0.58368 (6)	0.0170 (2)
C7	0.38214 (12)	0.26279 (12)	0.58260 (7)	0.0168 (2)
C8	0.20634 (12)	0.12648 (12)	0.50875 (7)	0.0179 (2)
C9	0.15860 (12)	0.20124 (13)	0.63796 (7)	0.0195 (2)
C10	0.29644 (12)	0.26900 (12)	0.64942 (7)	0.0180 (2)
C11	0.35166 (12)	0.33447 (13)	0.73048 (7)	0.0195 (2)
C12	0.56557 (14)	0.36010 (15)	0.82669 (7)	0.0265 (3)
H12A	0.5244	0.3313	0.8781	0.032*
H12B	0.5575	0.4667	0.8206	0.032*
C13	0.72342 (15)	0.31307 (17)	0.82954 (9)	0.0348 (3)
H13A	0.7293	0.2072	0.8342	0.042*
H13B	0.7805	0.3573	0.8775	0.042*
H13C	0.7631	0.3441	0.7788	0.042*
C14	0.05495 (14)	0.19872 (17)	0.70326 (7)	0.0289 (3)
H14A	−0.0326	0.1428	0.6833	0.035*
H14B	0.0265	0.2981	0.7156	0.035*
H14C	0.1033	0.1536	0.7536	0.035*
H3A	0.2163 (18)	0.0531 (17)	0.4007 (10)	0.027 (4)*
H3B	0.0792 (18)	0.0052 (18)	0.4373 (10)	0.026 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.02518 (17)	0.0389 (2)	0.02844 (18)	−0.01386 (12)	0.01160 (12)	−0.01141 (12)
O1	0.0209 (4)	0.0253 (4)	0.0167 (4)	−0.0010 (3)	−0.0005 (3)	0.0001 (3)
O2	0.0273 (5)	0.0363 (5)	0.0218 (4)	0.0029 (4)	0.0073 (3)	−0.0064 (4)
N1	0.0175 (4)	0.0199 (5)	0.0171 (4)	0.0003 (4)	0.0045 (3)	0.0011 (4)
N2	0.0171 (4)	0.0252 (5)	0.0174 (4)	−0.0008 (4)	0.0042 (3)	0.0017 (4)
N3	0.0218 (5)	0.0278 (5)	0.0200 (5)	−0.0061 (4)	0.0072 (4)	−0.0045 (4)
C1	0.0192 (5)	0.0204 (5)	0.0186 (5)	0.0005 (4)	0.0034 (4)	−0.0028 (4)
C2	0.0180 (5)	0.0265 (6)	0.0207 (5)	0.0005 (4)	0.0058 (4)	−0.0032 (4)
C3	0.0197 (5)	0.0260 (6)	0.0166 (5)	−0.0053 (4)	0.0046 (4)	−0.0003 (4)
C4	0.0263 (6)	0.0184 (5)	0.0182 (5)	−0.0022 (4)	0.0058 (4)	−0.0003 (4)
C5	0.0219 (5)	0.0197 (5)	0.0186 (5)	0.0028 (4)	0.0063 (4)	0.0014 (4)
C6	0.0176 (5)	0.0200 (5)	0.0136 (5)	0.0007 (4)	0.0031 (4)	0.0025 (4)
C7	0.0169 (5)	0.0172 (5)	0.0167 (5)	0.0031 (4)	0.0030 (4)	0.0032 (4)
C8	0.0183 (5)	0.0182 (5)	0.0176 (5)	0.0010 (4)	0.0034 (4)	0.0023 (4)
C9	0.0177 (5)	0.0248 (6)	0.0163 (5)	0.0016 (4)	0.0035 (4)	0.0034 (4)
C10	0.0179 (5)	0.0213 (5)	0.0152 (5)	0.0022 (4)	0.0034 (4)	0.0016 (4)
C11	0.0202 (5)	0.0228 (6)	0.0162 (5)	−0.0022 (4)	0.0046 (4)	0.0027 (4)
C12	0.0275 (6)	0.0311 (6)	0.0199 (6)	−0.0066 (5)	−0.0018 (5)	−0.0020 (5)
C13	0.0252 (6)	0.0399 (8)	0.0375 (7)	−0.0077 (6)	−0.0047 (5)	0.0003 (6)
C14	0.0218 (6)	0.0478 (8)	0.0182 (5)	−0.0063 (5)	0.0072 (4)	−0.0018 (5)

Geometric parameters (Å, º)

Cl—C3	1.7406 (12)	C4—H4	0.9500
O1—C11	1.3410 (14)	C5—C6	1.3960 (16)
O1—C12	1.4573 (14)	C5—H5	0.9500
O2—C11	1.2106 (15)	C6—C7	1.4851 (15)
N1—C7	1.3314 (14)	C7—C10	1.4098 (15)
N1—C8	1.3490 (14)	C9—C10	1.4049 (16)
N2—C9	1.3350 (15)	C9—C14	1.5005 (16)
N2—C8	1.3562 (14)	C10—C11	1.4880 (15)
N3—C8	1.3396 (15)	C12—C13	1.5077 (19)
N3—H3A	0.848 (17)	C12—H12A	0.9900
N3—H3B	0.873 (17)	C12—H12B	0.9900
C1—C2	1.3916 (16)	C13—H13A	0.9800
C1—C6	1.3950 (15)	C13—H13B	0.9800
C1—H1	0.9500	C13—H13C	0.9800
C2—C3	1.3894 (17)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.3866 (16)	C14—H14C	0.9800
C4—C5	1.3852 (16)
C11—O1—C12	116.89 (9)	N1—C8—N2	125.59 (10)
C7—N1—C8	116.67 (9)	N2—C9—C10	121.45 (10)
C9—N2—C8	117.29 (10)	N2—C9—C14	115.60 (10)
C8—N3—H3A	118.2 (11)	C10—C9—C14	122.92 (10)
C8—N3—H3B	118.4 (10)	C9—C10—C7	116.68 (10)
H3A—N3—H3B	123.4 (15)	C9—C10—C11	120.88 (10)
C2—C1—C6	120.73 (11)	C7—C10—C11	122.31 (10)
C2—C1—H1	119.6	O2—C11—O1	123.62 (11)
C6—C1—H1	119.6	O2—C11—C10	125.71 (11)
C3—C2—C1	118.67 (10)	O1—C11—C10	110.65 (9)
C3—C2—H2	120.7	O1—C12—C13	106.20 (10)
C1—C2—H2	120.7	O1—C12—H12A	110.5
C4—C3—C2	121.56 (11)	C13—C12—H12A	110.5
C4—C3—Cl	118.76 (9)	O1—C12—H12B	110.5
C2—C3—Cl	119.67 (9)	C13—C12—H12B	110.5
C5—C4—C3	119.12 (11)	H12A—C12—H12B	108.7
C5—C4—H4	120.4	C12—C13—H13A	109.5
C3—C4—H4	120.4	C12—C13—H13B	109.5
C4—C5—C6	120.63 (10)	H13A—C13—H13B	109.5
C4—C5—H5	119.7	C12—C13—H13C	109.5
C6—C5—H5	119.7	H13A—C13—H13C	109.5
C1—C6—C5	119.22 (10)	H13B—C13—H13C	109.5
C1—C6—C7	119.53 (10)	C9—C14—H14A	109.5
C5—C6—C7	121.24 (10)	C9—C14—H14B	109.5
N1—C7—C10	122.26 (10)	H14A—C14—H14B	109.5
N1—C7—C6	115.30 (9)	C9—C14—H14C	109.5
C10—C7—C6	122.42 (10)	H14A—C14—H14C	109.5
N3—C8—N1	117.39 (10)	H14B—C14—H14C	109.5
N3—C8—N2	117.03 (10)
C6—C1—C2—C3	−0.95 (17)	C9—N2—C8—N1	−1.82 (17)
C1—C2—C3—C4	−1.20 (18)	C8—N2—C9—C10	0.22 (16)
C1—C2—C3—Cl	177.55 (9)	C8—N2—C9—C14	−177.89 (11)
C2—C3—C4—C5	1.73 (18)	N2—C9—C10—C7	2.08 (16)
Cl—C3—C4—C5	−177.03 (9)	C14—C9—C10—C7	−179.96 (11)
C3—C4—C5—C6	−0.12 (17)	N2—C9—C10—C11	−173.79 (10)
C2—C1—C6—C5	2.51 (17)	C14—C9—C10—C11	4.17 (17)
C2—C1—C6—C7	−178.50 (10)	N1—C7—C10—C9	−3.13 (16)
C4—C5—C6—C1	−1.97 (16)	C6—C7—C10—C9	175.21 (10)
C4—C5—C6—C7	179.07 (10)	N1—C7—C10—C11	172.68 (10)
C8—N1—C7—C10	1.74 (15)	C6—C7—C10—C11	−8.98 (16)
C8—N1—C7—C6	−176.71 (9)	C12—O1—C11—O2	−11.42 (16)
C1—C6—C7—N1	−42.93 (14)	C12—O1—C11—C10	170.22 (9)
C5—C6—C7—N1	136.04 (11)	C9—C10—C11—O2	−48.80 (17)
C1—C6—C7—C10	138.62 (11)	C7—C10—C11—O2	135.56 (13)
C5—C6—C7—C10	−42.41 (15)	C9—C10—C11—O1	129.51 (11)
C7—N1—C8—N3	−179.30 (10)	C7—C10—C11—O1	−46.12 (14)
C7—N1—C8—N2	0.84 (16)	C11—O1—C12—C13	−167.26 (10)
C9—N2—C8—N3	178.32 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^i	0.848 (17)	2.287 (17)	3.0933 (13)	159.0 (15)
N3—H3B···N2^ii	0.873 (17)	2.161 (17)	3.0303 (14)	174.4 (15)
C14—H14C···Cl^iii	0.98	2.75	3.5543 (12)	139

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