3,4,6-Tri-amino-N-phenyl-thieno[2,3-b]pyridine-2-carboxamide.

In the title compound, C14H13N5OS, the dihedral angle between the fused ring system (r.m.s. deviation = 0.028 Å) and the phenyl ring is 48.24 (4)°. The mol-ecule features both an intra-molecular N-H⋯O and an N-H⋯N hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯O and N-H⋯N hydrogen bonds, generating a three-dimensional network. A weak N-H⋯π inter-action is also observed.

Related literature

For background to thieno­pyridine-containing compounds, see: Boschelli et al. (2008 ▶); Bakhite et al. (2002 ▶); Schnute et al. (2007 ▶).

Experimental

Crystal data

C14H13N5OS

M = 299.36

Monoclinic,

a = 5.2732 (7) Å

b = 21.028 (3) Å

c = 11.9777 (16) Å

β = 93.969 (2)°

V = 1325.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.21 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.85, T max = 0.98

24103 measured reflections

3500 independent reflections

3017 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.06

3500 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2013 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814013981/hb7235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013981/hb7235Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013981/hb7235Isup3.cml

CCDC reference: 1008299

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H13N5OS	F(000) = 624
Mr = 299.36	Dx = 1.501 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9996 reflections
a = 5.2732 (7) Å	θ = 2.6–29.1°
b = 21.028 (3) Å	µ = 0.25 mm−1
c = 11.9777 (16) Å	T = 150 K
β = 93.969 (2)°	Block, colourless
V = 1325.0 (3) Å3	0.21 × 0.13 × 0.09 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 1.9°
φ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −28→28
Tmin = 0.85, Tmax = 0.98	l = −16→16
24103 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.5972P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3500 reflections	Δρmax = 0.42 e Å−3
190 parameters	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
S1	0.40493 (6)	0.35471 (2)	0.83539 (3)	0.0168 (1)
O1	0.6615 (2)	0.47538 (5)	0.61593 (8)	0.0249 (3)
N1	0.0339 (2)	0.26672 (5)	0.82888 (9)	0.0169 (3)
N2	−0.2636 (2)	0.18599 (6)	0.82055 (10)	0.0230 (3)
N3	−0.1968 (2)	0.31627 (6)	0.49527 (10)	0.0220 (3)
N4	0.2168 (2)	0.41258 (6)	0.52579 (9)	0.0209 (3)
N5	0.7313 (2)	0.47187 (6)	0.80636 (10)	0.0196 (3)
C1	−0.1541 (3)	0.23617 (6)	0.76882 (11)	0.0168 (3)
C2	−0.2385 (3)	0.25273 (6)	0.65898 (11)	0.0170 (3)
C3	−0.1212 (3)	0.30131 (6)	0.60362 (11)	0.0161 (3)
C4	0.0807 (2)	0.33451 (6)	0.66470 (10)	0.0150 (3)
C5	0.1430 (2)	0.31391 (6)	0.77427 (10)	0.0149 (3)
C6	0.2455 (3)	0.38441 (6)	0.63091 (11)	0.0157 (3)
C7	0.4308 (3)	0.40001 (6)	0.71359 (10)	0.0163 (3)
C8	0.6148 (3)	0.45111 (6)	0.70611 (11)	0.0172 (3)
C9	0.9058 (3)	0.52266 (6)	0.82104 (11)	0.0178 (3)
C10	1.0866 (3)	0.53587 (7)	0.74444 (12)	0.0199 (4)
C11	1.2629 (3)	0.58416 (7)	0.76735 (14)	0.0245 (4)
C12	1.2616 (3)	0.61978 (7)	0.86512 (14)	0.0261 (4)
C13	1.0791 (3)	0.60708 (7)	0.94063 (13)	0.0236 (4)
C14	0.9013 (3)	0.55895 (7)	0.91876 (12)	0.0207 (4)
H2	−0.37710	0.23050	0.62220	0.0200*
H2A	−0.17740	0.16940	0.88230	0.0280*
H2B	−0.36030	0.15820	0.77790	0.0280*
H3A	−0.29050	0.28560	0.45810	0.0260*
H3B	−0.07270	0.33330	0.45530	0.0260*
H4A	0.05280	0.42370	0.50670	0.0250*
H4B	0.33410	0.44320	0.51430	0.0250*
H5A	0.66340	0.45840	0.87010	0.0230*
H10	1.08930	0.51200	0.67710	0.0240*
H11	1.38620	0.59300	0.71530	0.0290*
H12	1.38390	0.65240	0.88020	0.0310*
H13	1.07580	0.63140	1.00740	0.0280*
H14	0.77650	0.55070	0.97040	0.0250*

	U11	U22	U33	U12	U13	U23
S1	0.0174 (2)	0.0186 (2)	0.0138 (2)	−0.0032 (1)	−0.0034 (1)	0.0018 (1)
O1	0.0273 (6)	0.0270 (5)	0.0196 (5)	−0.0099 (4)	−0.0033 (4)	0.0059 (4)
N1	0.0165 (6)	0.0174 (5)	0.0167 (5)	−0.0011 (4)	0.0000 (4)	0.0018 (4)
N2	0.0234 (6)	0.0229 (6)	0.0223 (6)	−0.0066 (5)	−0.0008 (5)	0.0051 (5)
N3	0.0243 (6)	0.0263 (6)	0.0147 (5)	−0.0084 (5)	−0.0037 (4)	0.0006 (5)
N4	0.0256 (6)	0.0215 (6)	0.0151 (5)	−0.0059 (5)	−0.0027 (5)	0.0044 (4)
N5	0.0211 (6)	0.0193 (6)	0.0180 (5)	−0.0064 (4)	−0.0012 (4)	0.0003 (4)
C1	0.0152 (6)	0.0166 (6)	0.0187 (6)	0.0005 (5)	0.0028 (5)	−0.0001 (5)
C2	0.0155 (6)	0.0177 (6)	0.0175 (6)	−0.0021 (5)	−0.0001 (5)	−0.0016 (5)
C3	0.0162 (6)	0.0173 (6)	0.0145 (6)	0.0001 (5)	−0.0003 (5)	−0.0015 (5)
C4	0.0168 (6)	0.0149 (6)	0.0131 (6)	−0.0007 (5)	−0.0006 (5)	−0.0002 (4)
C5	0.0141 (6)	0.0156 (6)	0.0145 (6)	−0.0001 (4)	−0.0016 (5)	−0.0011 (4)
C6	0.0178 (6)	0.0151 (6)	0.0140 (5)	−0.0009 (5)	0.0003 (5)	−0.0005 (4)
C7	0.0181 (6)	0.0163 (6)	0.0142 (6)	−0.0020 (5)	−0.0004 (5)	0.0019 (5)
C8	0.0160 (6)	0.0165 (6)	0.0188 (6)	−0.0012 (5)	−0.0018 (5)	0.0004 (5)
C9	0.0162 (6)	0.0147 (6)	0.0218 (6)	−0.0004 (5)	−0.0044 (5)	0.0019 (5)
C10	0.0169 (6)	0.0184 (6)	0.0242 (7)	0.0010 (5)	−0.0008 (5)	0.0001 (5)
C11	0.0158 (7)	0.0237 (7)	0.0338 (8)	−0.0020 (5)	−0.0003 (6)	0.0045 (6)
C12	0.0206 (7)	0.0187 (7)	0.0375 (8)	−0.0043 (5)	−0.0079 (6)	0.0019 (6)
C13	0.0246 (7)	0.0184 (7)	0.0264 (7)	−0.0003 (5)	−0.0081 (6)	−0.0020 (5)
C14	0.0201 (7)	0.0200 (6)	0.0214 (6)	−0.0009 (5)	−0.0030 (5)	0.0000 (5)

S1—C5	1.7435 (12)	C2—C3	1.3866 (19)
S1—C7	1.7555 (13)	C3—C4	1.4312 (19)
O1—C8	1.2348 (17)	C4—C6	1.4383 (18)
N1—C1	1.3470 (18)	C4—C5	1.3994 (17)
N1—C5	1.3400 (16)	C6—C7	1.382 (2)
N2—C1	1.3712 (18)	C7—C8	1.455 (2)
N3—C3	1.3677 (18)	C9—C10	1.396 (2)
N4—C6	1.3902 (17)	C9—C14	1.399 (2)
N5—C8	1.3812 (18)	C10—C11	1.391 (2)
N5—C9	1.4128 (18)	C11—C12	1.391 (2)
N2—H2B	0.9100	C12—C13	1.391 (2)
N2—H2A	0.9100	C13—C14	1.392 (2)
N3—H3B	0.9100	C2—H2	0.9500
N3—H3A	0.9100	C10—H10	0.9500
N4—H4A	0.9100	C11—H11	0.9500
N4—H4B	0.9100	C12—H12	0.9500
N5—H5A	0.9100	C13—H13	0.9500
C1—C2	1.4033 (19)	C14—H14	0.9500
C5—S1—C7	91.32 (6)	N4—C6—C7	125.12 (13)
C1—N1—C5	114.68 (11)	C4—C6—C7	112.50 (11)
C8—N5—C9	126.43 (12)	C6—C7—C8	124.95 (12)
C1—N2—H2B	119.00	S1—C7—C6	112.03 (10)
H2A—N2—H2B	116.00	S1—C7—C8	122.86 (10)
C1—N2—H2A	117.00	O1—C8—N5	121.75 (13)
C3—N3—H3B	115.00	O1—C8—C7	122.24 (12)
H3A—N3—H3B	114.00	N5—C8—C7	116.00 (11)
C3—N3—H3A	114.00	C10—C9—C14	119.56 (13)
C6—N4—H4B	114.00	N5—C9—C10	122.49 (12)
H4A—N4—H4B	115.00	N5—C9—C14	117.90 (13)
C6—N4—H4A	112.00	C9—C10—C11	119.54 (13)
C9—N5—H5A	115.00	C10—C11—C12	121.14 (15)
C8—N5—H5A	117.00	C11—C12—C13	119.21 (14)
N1—C1—C2	123.80 (12)	C12—C13—C14	120.29 (14)
N2—C1—C2	119.90 (13)	C9—C14—C13	120.26 (14)
N1—C1—N2	116.30 (12)	C1—C2—H2	120.00
C1—C2—C3	120.54 (13)	C3—C2—H2	120.00
N3—C3—C4	122.04 (12)	C9—C10—H10	120.00
N3—C3—C2	120.86 (13)	C11—C10—H10	120.00
C2—C3—C4	117.10 (12)	C10—C11—H11	119.00
C5—C4—C6	112.49 (11)	C12—C11—H11	119.00
C3—C4—C6	130.89 (12)	C11—C12—H12	120.00
C3—C4—C5	116.52 (11)	C13—C12—H12	120.00
S1—C5—C4	111.67 (9)	C12—C13—H13	120.00
N1—C5—C4	127.31 (11)	C14—C13—H13	120.00
S1—C5—N1	120.92 (9)	C9—C14—H14	120.00
N4—C6—C4	122.39 (12)	C13—C14—H14	120.00
C7—S1—C5—N1	176.86 (11)	C6—C4—C5—S1	−0.75 (14)
C7—S1—C5—C4	0.24 (10)	C6—C4—C5—N1	−177.10 (12)
C5—S1—C7—C6	0.35 (11)	C3—C4—C6—N4	4.6 (2)
C5—S1—C7—C8	175.81 (12)	C3—C4—C6—C7	−175.08 (13)
C5—N1—C1—N2	177.57 (11)	C5—C4—C6—N4	−179.26 (12)
C5—N1—C1—C2	−1.99 (19)	C5—C4—C6—C7	1.02 (16)
C1—N1—C5—S1	−175.21 (10)	N4—C6—C7—S1	179.46 (11)
C1—N1—C5—C4	0.84 (18)	N4—C6—C7—C8	4.1 (2)
C9—N5—C8—O1	2.2 (2)	C4—C6—C7—S1	−0.83 (15)
C9—N5—C8—C7	−176.62 (13)	C4—C6—C7—C8	−176.18 (13)
C8—N5—C9—C10	−36.6 (2)	S1—C7—C8—O1	167.43 (11)
C8—N5—C9—C14	146.03 (14)	S1—C7—C8—N5	−13.78 (18)
N1—C1—C2—C3	2.8 (2)	C6—C7—C8—O1	−17.7 (2)
N2—C1—C2—C3	−176.78 (13)	C6—C7—C8—N5	161.09 (14)
C1—C2—C3—N3	177.76 (13)	N5—C9—C10—C11	−176.08 (14)
C1—C2—C3—C4	−2.1 (2)	C14—C9—C10—C11	1.2 (2)
N3—C3—C4—C5	−178.88 (12)	N5—C9—C14—C13	176.12 (13)
N3—C3—C4—C6	−2.9 (2)	C10—C9—C14—C13	−1.3 (2)
C2—C3—C4—C5	1.00 (18)	C9—C10—C11—C12	−0.3 (2)
C2—C3—C4—C6	176.98 (14)	C10—C11—C12—C13	−0.6 (2)
C3—C4—C5—S1	175.96 (9)	C11—C12—C13—C14	0.5 (2)
C3—C4—C5—N1	−0.39 (19)	C12—C13—C14—C9	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4i	0.91	2.52	3.2226 (17)	134
N3—H3A···N1ii	0.91	2.07	2.9398 (17)	161
N3—H3B···N4	0.91	2.38	2.9802 (17)	124
N3—H3B···N2iii	0.91	2.41	3.2034 (16)	146
N4—H4B···O1	0.91	2.15	2.8387 (16)	132
N4—H4B···O1iv	0.91	2.32	2.9991 (16)	132
N2—H2B···Cg3v	0.91	2.56	3.4662 (14)	173

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N4i	0.91	2.52	3.2226 (17)	134
N3—H3A⋯N1ii	0.91	2.07	2.9398 (17)	161
N3—H3B⋯N4	0.91	2.38	2.9802 (17)	124
N3—H3B⋯N2iii	0.91	2.41	3.2034 (16)	146
N4—H4B⋯O1	0.91	2.15	2.8387 (16)	132
N4—H4B⋯O1iv	0.91	2.32	2.9991 (16)	132
N2—H2B⋯Cg3v	0.91	2.56	3.4662 (14)	173

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .