N-(3-Methoxy-5-methyl­pyrazin-2-yl)-2-[4-(1,3,4-oxa­diazol-2-yl)­phenyl]­pyridine-3-sulfon­amide (ZD4054 Form 1)

The title compound, C₁₉H₁₆N₆O₄S, crystallizes from N-methyl­pyridine in the centrosymmetric space group P2₁/n with four mol­ecules in the unit cell. The mol­ecule has 11 heteroatoms, of which only one is protonated. This potential hydrogen-bond donor, viz. the NH amide group, participates in both intra- and intermolecular hydrogen-bond interactions, thus contributing to the stabilization of the molecular conformation and the linking of mol­ecules as dimers. The hairpin-like folded mol­ecule is arranged with three of its four aromatic rings in two parallel planes intersected by a sulfon­amide moiety. In this way, the mol­ecules stack efficiently, facilitated by short-range van der Waals forces. No residual volume for solvent inclusion was found.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.127
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O26     ..       5.78 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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: KappaCCD Software (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976), PLATON (Spek, 2003) and Mercury (Bruno et al., 2002); software used to prepare material for publication: PLATON.

N-(3-Methoxy-5-methylpyrazin-2-yl)-2-[4-(1,3,4-oxadiazol-2- yl)phenyl]pyridine-3-sulfonamide

Crystal data

C19H16N6O4S	F(000) = 880
Mr = 424.44	Dx = 1.455 Mg m^−3
Monoclinic, P21/n	Melting point: 518 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.310 (1) Å	Cell parameters from 7434 reflections
b = 15.132 (1) Å	θ = 3.6–27.5°
c = 15.414 (1) Å	µ = 0.21 mm^−1
β = 90.79 (1)°	T = 293 K
V = 1938.1 (3) Å^3	Rhombohedral, colourless
Z = 4	0.17 × 0.17 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 3.6°
φ and ω scans with κ offsets	h = −10→10
7434 measured reflections	k = −17→19
4382 independent reflections	l = −19→19
2604 reflections with I > 2σ(I)

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0686P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
4382 reflections	Δρmax = 0.21 e Å^−3
276 parameters	Δρmin = −0.34 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Crystals from: N-methyl pyridine, NMP Number of collected frames: 111 Number of repeats: 1 Crystal-Detector distance (mm): 30 Exposure time (sec) per frame: 30 Phi-rotation step: 2

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 on F^{2 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 F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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
S1	0.69000 (6)	−0.07388 (3)	0.33321 (3)	0.04461 (17)
O22	1.06339 (19)	0.18304 (12)	−0.02227 (10)	0.0680 (5)
O26	0.81287 (16)	−0.13044 (9)	0.30024 (9)	0.0539 (4)
O27	0.56291 (17)	−0.11372 (10)	0.38043 (9)	0.0572 (4)
O28	0.57806 (18)	0.07864 (11)	0.10839 (9)	0.0617 (4)
N2	0.61809 (19)	−0.02184 (12)	0.24872 (11)	0.0461 (4)
H2	0.670 (3)	−0.0337 (16)	0.2010 (15)	0.064 (2)*
N4	0.4513 (2)	0.07338 (11)	0.32678 (11)	0.0494 (4)
N7	0.42187 (19)	0.18182 (12)	0.18056 (11)	0.0499 (4)
N13	0.9248 (2)	0.14093 (13)	0.42777 (12)	0.0602 (5)
N24	1.2149 (2)	0.09397 (15)	−0.09758 (11)	0.0605 (5)
N25	1.1936 (2)	0.05764 (13)	−0.01495 (11)	0.0564 (5)
C3	0.5205 (2)	0.05357 (13)	0.25384 (13)	0.0435 (5)
C5	0.3639 (2)	0.14933 (15)	0.32662 (15)	0.0539 (6)
H5	0.3107	0.1651	0.3770	0.064 (2)*
C6	0.3506 (2)	0.20355 (14)	0.25632 (15)	0.0493 (5)
C8	0.5033 (2)	0.10821 (15)	0.17954 (13)	0.0468 (5)
C9	0.7731 (2)	0.00917 (13)	0.40210 (12)	0.0409 (5)
C10	0.7252 (2)	0.00814 (15)	0.48741 (13)	0.0508 (5)
H10	0.6563	−0.0357	0.5070	0.064 (2)*
C11	0.7804 (3)	0.07251 (17)	0.54309 (14)	0.0571 (6)
H11	0.7520	0.0724	0.6012	0.064 (2)*
C12	0.8778 (3)	0.13653 (17)	0.51069 (15)	0.0645 (7)
H12	0.9143	0.1802	0.5486	0.064 (2)*
C14	0.8758 (2)	0.07649 (13)	0.37381 (13)	0.0423 (5)
C15	0.9342 (2)	0.08519 (13)	0.28341 (13)	0.0408 (5)
C16	1.0338 (2)	0.02162 (14)	0.24716 (13)	0.0465 (5)
H16	1.0625	−0.0279	0.2795	0.064 (2)*
C17	1.0901 (2)	0.03091 (14)	0.16439 (13)	0.0456 (5)
H17	1.1574	−0.0119	0.1412	0.064 (2)*
C18	1.0465 (2)	0.10456 (14)	0.11510 (12)	0.0411 (5)
C19	0.9502 (2)	0.16914 (14)	0.15074 (13)	0.0461 (5)
H19	0.9219	0.2188	0.1184	0.064 (2)*
C20	0.8962 (2)	0.15960 (14)	0.23461 (13)	0.0467 (5)
H20	0.8333	0.2038	0.2588	0.064 (2)*
C21	1.1046 (2)	0.11161 (14)	0.02630 (13)	0.0439 (5)
C23	1.1370 (3)	0.16593 (19)	−0.09825 (15)	0.0659 (7)
H23	1.1310	0.2032	−0.1461	0.064 (2)*
C29	0.5799 (3)	0.1351 (2)	0.03322 (15)	0.0787 (9)
H29A	0.6373	0.1064	−0.0125	0.105 (4)*
H29B	0.6321	0.1898	0.0477	0.105 (4)*
H29C	0.4714	0.1467	0.0143	0.105 (4)*
C30	0.2602 (3)	0.28925 (15)	0.25935 (18)	0.0684 (7)
H30A	0.3352	0.3375	0.2598	0.105 (4)*
H30B	0.1969	0.2912	0.3109	0.105 (4)*
H30C	0.1908	0.2938	0.2093	0.105 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0549 (3)	0.0352 (3)	0.0438 (3)	−0.0010 (2)	0.0021 (2)	0.0024 (2)
O22	0.0866 (11)	0.0633 (11)	0.0547 (10)	0.0144 (9)	0.0215 (8)	0.0130 (9)
O26	0.0652 (8)	0.0405 (9)	0.0562 (9)	0.0115 (7)	0.0041 (7)	−0.0028 (7)
O27	0.0683 (9)	0.0442 (9)	0.0595 (9)	−0.0119 (7)	0.0123 (7)	0.0072 (7)
O28	0.0714 (10)	0.0708 (12)	0.0432 (9)	0.0074 (8)	0.0057 (7)	0.0122 (8)
N2	0.0534 (10)	0.0472 (11)	0.0375 (10)	0.0039 (8)	−0.0005 (7)	0.0015 (8)
N4	0.0580 (10)	0.0425 (11)	0.0478 (11)	0.0022 (8)	0.0047 (8)	0.0036 (9)
N7	0.0479 (9)	0.0471 (11)	0.0544 (11)	−0.0067 (8)	−0.0056 (8)	0.0077 (9)
N13	0.0721 (12)	0.0588 (13)	0.0498 (11)	−0.0145 (9)	0.0061 (9)	−0.0122 (10)
N24	0.0636 (11)	0.0760 (15)	0.0421 (11)	−0.0005 (11)	0.0069 (9)	0.0004 (10)
N25	0.0643 (11)	0.0634 (13)	0.0417 (10)	0.0072 (9)	0.0094 (8)	0.0002 (9)
C3	0.0425 (11)	0.0412 (12)	0.0466 (12)	−0.0045 (8)	−0.0033 (9)	0.0023 (10)
C5	0.0594 (13)	0.0461 (14)	0.0565 (14)	−0.0001 (10)	0.0075 (10)	−0.0020 (11)
C6	0.0473 (11)	0.0389 (13)	0.0616 (14)	−0.0076 (9)	−0.0052 (10)	0.0034 (11)
C8	0.0451 (11)	0.0503 (14)	0.0450 (12)	−0.0066 (10)	−0.0032 (9)	0.0054 (11)
C9	0.0478 (10)	0.0374 (12)	0.0375 (11)	0.0046 (8)	−0.0020 (8)	0.0027 (9)
C10	0.0583 (12)	0.0527 (14)	0.0414 (12)	−0.0008 (10)	0.0014 (9)	0.0054 (11)
C11	0.0662 (14)	0.0698 (17)	0.0354 (12)	−0.0007 (12)	0.0011 (10)	−0.0019 (12)
C12	0.0808 (15)	0.0645 (17)	0.0482 (14)	−0.0093 (13)	0.0002 (12)	−0.0172 (12)
C14	0.0451 (10)	0.0384 (12)	0.0432 (11)	0.0044 (9)	0.0005 (8)	−0.0033 (10)
C15	0.0424 (10)	0.0366 (11)	0.0436 (11)	−0.0043 (8)	0.0033 (8)	−0.0039 (10)
C16	0.0531 (11)	0.0385 (12)	0.0480 (13)	0.0067 (9)	0.0040 (9)	0.0048 (10)
C17	0.0493 (11)	0.0390 (12)	0.0488 (12)	0.0040 (9)	0.0059 (9)	−0.0038 (10)
C18	0.0430 (10)	0.0370 (12)	0.0435 (11)	−0.0061 (8)	0.0040 (8)	−0.0026 (9)
C19	0.0528 (11)	0.0380 (12)	0.0477 (12)	0.0009 (9)	0.0037 (9)	0.0055 (10)
C20	0.0510 (11)	0.0377 (12)	0.0518 (13)	0.0018 (9)	0.0113 (9)	−0.0030 (10)
C21	0.0435 (10)	0.0432 (13)	0.0451 (12)	−0.0056 (9)	0.0007 (9)	0.0029 (10)
C23	0.0740 (15)	0.077 (2)	0.0471 (14)	−0.0009 (14)	0.0142 (11)	0.0118 (13)
C29	0.0782 (16)	0.107 (2)	0.0510 (15)	0.0100 (15)	0.0084 (12)	0.0281 (15)
C30	0.0747 (15)	0.0410 (14)	0.0892 (19)	−0.0002 (11)	−0.0064 (13)	0.0037 (13)

Geometric parameters (Å, º)

S1—O27	1.4247 (13)	C10—C11	1.373 (3)
S1—O26	1.4309 (14)	C10—H10	0.9300
S1—N2	1.6284 (18)	C11—C12	1.362 (3)
S1—C9	1.779 (2)	C11—H11	0.9300
O22—C23	1.354 (3)	C12—H12	0.9300
O22—C21	1.356 (3)	C14—C15	1.488 (3)
O28—C8	1.344 (2)	C15—C20	1.388 (3)
O28—C29	1.439 (3)	C15—C16	1.391 (3)
N2—C3	1.403 (3)	C16—C17	1.372 (3)
N2—H2	0.88 (2)	C16—H16	0.9300
N4—C3	1.305 (2)	C17—C18	1.394 (3)
N4—C5	1.359 (3)	C17—H17	0.9300
N7—C8	1.304 (3)	C18—C19	1.382 (3)
N7—C6	1.357 (3)	C18—C21	1.462 (3)
N13—C14	1.341 (3)	C19—C20	1.382 (3)
N13—C12	1.343 (3)	C19—H19	0.9300
N24—C23	1.267 (3)	C20—H20	0.9300
N24—N25	1.401 (2)	C23—H23	0.9300
N25—C21	1.277 (3)	C29—H29A	0.9600
C3—C8	1.418 (3)	C29—H29B	0.9600
C5—C6	1.362 (3)	C29—H29C	0.9600
C5—H5	0.9300	C30—H30A	0.9600
C6—C30	1.499 (3)	C30—H30B	0.9600
C9—C10	1.379 (3)	C30—H30C	0.9600
C9—C14	1.402 (3)
O26—S1—O27	117.77 (9)	C17—C18—C21	118.82 (17)
O26—S1—N2	105.13 (9)	C17—C18—C19	119.76 (18)
O26—S1—C9	111.20 (8)	C19—C18—C21	121.42 (18)
O27—S1—N2	110.29 (9)	C18—C19—C20	119.70 (19)
O27—S1—C9	106.17 (9)	C15—C20—C19	121.15 (18)
N2—S1—C9	105.72 (9)	O22—C21—N25	112.23 (18)
C21—O22—C23	102.21 (18)	O22—C21—C18	119.41 (17)
C8—O28—C29	117.97 (18)	N25—C21—C18	128.36 (19)
S1—N2—C3	123.67 (14)	O22—C23—N24	113.2 (2)
C3—N4—C5	115.75 (18)	N4—C5—H5	118.39
C6—N7—C8	116.76 (18)	C6—C5—H5	118.38
C12—N13—C14	117.66 (19)	C9—C10—H10	120.33
N25—N24—C23	105.89 (18)	C11—C10—H10	120.35
N24—N25—C21	106.44 (18)	C10—C11—H11	120.94
C3—N2—H2	120.4 (16)	C12—C11—H11	120.99
S1—N2—H2	113.1 (16)	N13—C12—H12	117.77
N2—C3—C8	118.73 (17)	C11—C12—H12	117.73
N2—C3—N4	119.83 (18)	C15—C16—H16	119.46
N4—C3—C8	121.41 (18)	C17—C16—H16	119.54
N4—C5—C6	123.2 (2)	C16—C17—H17	120.02
C5—C6—C30	122.1 (2)	C18—C17—H17	120.02
N7—C6—C30	117.5 (2)	C18—C19—H19	120.12
N7—C6—C5	120.46 (19)	C20—C19—H19	120.18
O28—C8—N7	122.68 (19)	C15—C20—H20	119.41
O28—C8—C3	114.97 (18)	C19—C20—H20	119.44
N7—C8—C3	122.35 (18)	O22—C23—H23	123.41
S1—C9—C10	116.52 (15)	N24—C23—H23	123.37
C10—C9—C14	119.31 (18)	O28—C29—H29A	109.46
S1—C9—C14	124.09 (15)	O28—C29—H29B	109.54
C9—C10—C11	119.32 (19)	O28—C29—H29C	109.43
C10—C11—C12	118.1 (2)	H29A—C29—H29B	109.47
N13—C12—C11	124.5 (2)	H29A—C29—H29C	109.49
N13—C14—C15	114.60 (17)	H29B—C29—H29C	109.43
N13—C14—C9	121.07 (18)	C6—C30—H30A	109.42
C9—C14—C15	124.29 (17)	C6—C30—H30B	109.45
C16—C15—C20	118.39 (18)	C6—C30—H30C	109.44
C14—C15—C20	120.31 (17)	H30A—C30—H30B	109.51
C14—C15—C16	121.24 (18)	H30A—C30—H30C	109.53
C15—C16—C17	121.00 (19)	H30B—C30—H30C	109.48
C16—C17—C18	119.95 (18)
O26—S1—N2—C3	−165.48 (15)	N4—C3—C8—N7	1.9 (3)
O27—S1—N2—C3	66.60 (17)	N2—C3—C8—N7	−176.22 (17)
C9—S1—N2—C3	−47.76 (17)	N4—C3—C8—O28	−178.50 (17)
O26—S1—C9—C10	−117.65 (15)	N4—C5—C6—N7	2.2 (3)
O26—S1—C9—C14	65.60 (18)	N4—C5—C6—C30	−176.85 (19)
O27—S1—C9—C10	11.60 (17)	S1—C9—C10—C11	−177.59 (17)
O27—S1—C9—C14	−165.14 (15)	C14—C9—C10—C11	−0.7 (3)
N2—S1—C9—C10	128.78 (15)	C10—C9—C14—C15	−179.32 (17)
C14—C9—S1—N2	−47.97 (18)	S1—C9—C14—N13	175.00 (14)
C21—O22—C23—N24	−0.4 (3)	S1—C9—C14—C15	−2.7 (3)
C23—O22—C21—N25	0.4 (2)	C10—C9—C14—N13	−1.7 (3)
C23—O22—C21—C18	−179.68 (18)	C9—C10—C11—C12	1.7 (3)
C29—O28—C8—N7	5.9 (3)	C10—C11—C12—N13	−0.4 (4)
C29—O28—C8—C3	−173.67 (18)	N13—C14—C15—C20	−59.5 (2)
S1—N2—C3—N4	−16.4 (3)	C9—C14—C15—C16	−64.7 (2)
S1—N2—C3—C8	161.75 (14)	N13—C14—C15—C16	117.5 (2)
C3—N4—C5—C6	−1.5 (3)	C9—C14—C15—C20	118.3 (2)
C5—N4—C3—N2	177.64 (17)	C14—C15—C16—C17	−178.60 (17)
C5—N4—C3—C8	−0.5 (3)	C20—C15—C16—C17	−1.6 (3)
C6—N7—C8—C3	−1.2 (3)	C16—C15—C20—C19	2.6 (3)
C8—N7—C6—C5	−0.7 (3)	C14—C15—C20—C19	179.57 (17)
C8—N7—C6—C30	178.37 (18)	C15—C16—C17—C18	−0.5 (3)
C6—N7—C8—O28	179.23 (17)	C16—C17—C18—C19	1.8 (3)
C14—N13—C12—C11	−1.9 (3)	C16—C17—C18—C21	−178.35 (17)
C12—N13—C14—C9	2.9 (3)	C19—C18—C21—N25	180.0 (2)
C12—N13—C14—C15	−179.27 (18)	C21—C18—C19—C20	179.28 (17)
C23—N24—N25—C21	−0.1 (2)	C19—C18—C21—O22	0.1 (3)
N25—N24—C23—O22	0.3 (3)	C17—C18—C19—C20	−0.8 (3)
N24—N25—C21—O22	−0.2 (2)	C17—C18—C21—O22	−179.83 (17)
N24—N25—C21—C18	179.85 (18)	C17—C18—C21—N25	0.1 (3)
N2—C3—C8—O28	3.4 (3)	C18—C19—C20—C15	−1.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O28	0.88 (2)	2.34 (2)	2.661 (2)	101.7 (18)
N2—H2···N24^i	0.88 (2)	2.08 (2)	2.938 (2)	166 (2)
C10—H10···O27	0.93	2.40	2.807 (3)	106
C19—H19···O27^ii	0.93	2.54	3.322 (3)	142

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