Download citation
Download citation
link to html
In the title compound, C5H6BrClN4, inter­molecular N—H...N hydrogen bonds link the mol­ecules into tapes containing R22(8) loops.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017552/bi2181sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017552/bi2181Isup2.hkl
Contains datablock I

CCDC reference: 651383

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.018
  • wR factor = 0.043
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90 PLAT432_ALERT_2_C Short Inter X...Y Contact Br1 .. C5 .. 3.34 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. N3 .. 2.65 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.896 Tmax scaled 0.451 Tmin scaled 0.187
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

5-Bromo-6-chloro-N4-methylpyrimidine-2,4-diamine top
Crystal data top
C5H6BrClN4F(000) = 928
Mr = 237.50Dx = 2.076 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3319 reflections
a = 9.6480 (2) Åθ = 2.9–27.5°
b = 10.8032 (3) ŵ = 5.69 mm1
c = 15.1157 (3) ÅT = 120 K
β = 105.2600 (14)°Cut block, colourless
V = 1519.95 (6) Å30.40 × 0.18 × 0.14 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
1761 independent reflections
Radiation source: fine-focus sealed tube1645 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and φ scansθmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1212
Tmin = 0.209, Tmax = 0.503k = 1314
15792 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap (N-H) and geom (C-H)
R[F2 > 2σ(F2)] = 0.018H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.043 w = 1/[σ2(Fo2) + (0.0155P)2 + 2.8831P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1761 reflectionsΔρmax = 0.49 e Å3
111 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00418 (17)
Special details top

Experimental. νmax (KBr) 3455, 3299 (NH2), 1631 (NH2), 1549 (C=N, conjugated, cyclic), 1449 (CH3), 1059 (pyrimidyl Br)

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 (Å2) top
xyzUiso*/Ueq
C10.18840 (17)0.41559 (15)0.01735 (11)0.0110 (3)
C20.11792 (16)0.35381 (15)0.03681 (11)0.0106 (3)
C30.19360 (17)0.34057 (15)0.13061 (11)0.0109 (3)
C40.38175 (17)0.44805 (15)0.10227 (11)0.0102 (3)
C50.22020 (19)0.24473 (18)0.28090 (12)0.0160 (4)
H5A0.17910.17110.30220.024*
H5B0.21640.31460.32160.024*
H5C0.32030.22830.28140.024*
N10.32309 (15)0.39288 (13)0.16339 (9)0.0113 (3)
N20.32026 (14)0.46195 (13)0.01165 (9)0.0109 (3)
H10.561 (2)0.4686 (19)0.1836 (15)0.013*
H20.563 (2)0.5089 (19)0.0945 (14)0.013*
N30.51530 (15)0.49650 (14)0.13533 (11)0.0125 (3)
N40.13838 (16)0.27459 (14)0.18834 (11)0.0142 (3)
H30.069 (2)0.235 (2)0.1675 (16)0.017*
Cl10.10730 (4)0.43702 (4)0.13350 (3)0.01564 (10)
Br10.065566 (16)0.283174 (15)0.006696 (11)0.01344 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0119 (8)0.0109 (8)0.0098 (7)0.0023 (6)0.0023 (6)0.0011 (6)
C20.0075 (7)0.0114 (8)0.0122 (8)0.0002 (6)0.0014 (6)0.0020 (6)
C30.0100 (7)0.0105 (8)0.0125 (8)0.0008 (6)0.0037 (6)0.0008 (6)
C40.0113 (7)0.0088 (8)0.0108 (7)0.0014 (6)0.0037 (6)0.0013 (6)
C50.0161 (8)0.0209 (9)0.0111 (8)0.0017 (7)0.0036 (7)0.0029 (7)
N10.0101 (6)0.0126 (7)0.0110 (7)0.0006 (5)0.0027 (5)0.0002 (5)
N20.0104 (7)0.0115 (7)0.0110 (7)0.0000 (5)0.0029 (5)0.0000 (5)
N30.0097 (7)0.0179 (7)0.0101 (7)0.0028 (6)0.0026 (6)0.0009 (6)
N40.0098 (7)0.0179 (8)0.0141 (7)0.0050 (6)0.0017 (6)0.0025 (6)
Cl10.0160 (2)0.0206 (2)0.00899 (19)0.00034 (16)0.00085 (15)0.00127 (15)
Br10.00922 (10)0.01639 (11)0.01360 (11)0.00244 (6)0.00105 (7)0.00176 (6)
Geometric parameters (Å, º) top
C1—N21.330 (2)C4—N31.358 (2)
C1—C21.368 (2)C5—N41.450 (2)
C1—Cl11.7394 (16)C5—H5A0.980
C2—C31.421 (2)C5—H5B0.980
C2—Br11.8804 (16)C5—H5C0.980
C3—N41.341 (2)N3—H10.81 (2)
C3—N11.342 (2)N3—H20.87 (2)
C4—N11.343 (2)N4—H30.78 (2)
C4—N21.350 (2)
N2—C1—C2124.73 (15)N4—C5—H5B109.5
N2—C1—Cl1114.82 (12)H5A—C5—H5B109.5
C2—C1—Cl1120.44 (12)N4—C5—H5C109.5
C1—C2—C3116.14 (14)H5A—C5—H5C109.5
C1—C2—Br1124.00 (12)H5B—C5—H5C109.5
C3—C2—Br1119.82 (12)C3—N1—C4116.93 (14)
N4—C3—N1118.33 (15)C1—N2—C4114.79 (14)
N4—C3—C2121.00 (15)C4—N3—H1115.4 (15)
N1—C3—C2120.67 (15)C4—N3—H2115.2 (13)
N1—C4—N2126.51 (15)H1—N3—H2115.7 (19)
N1—C4—N3116.65 (14)C3—N4—C5122.51 (15)
N2—C4—N3116.83 (15)C3—N4—H3117.9 (17)
N4—C5—H5A109.5C5—N4—H3117.2 (17)
N2—C1—C2—C30.5 (2)C2—C3—N1—C45.6 (2)
Cl1—C1—C2—C3179.66 (12)N2—C4—N1—C33.7 (2)
N2—C1—C2—Br1177.31 (13)N3—C4—N1—C3177.44 (15)
Cl1—C1—C2—Br11.9 (2)C2—C1—N2—C42.4 (2)
C1—C2—C3—N4175.55 (16)Cl1—C1—N2—C4178.39 (12)
Br1—C2—C3—N42.3 (2)N1—C4—N2—C10.2 (2)
C1—C2—C3—N13.7 (2)N3—C4—N2—C1178.57 (14)
Br1—C2—C3—N1178.36 (12)N1—C3—N4—C58.0 (3)
N4—C3—N1—C4173.68 (15)C2—C3—N4—C5171.29 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1···N1i0.81 (2)2.43 (2)3.232 (2)173.4 (19)
N3—H2···N2ii0.87 (2)2.21 (2)3.084 (2)178.5 (19)
N4—H3···N3iii0.78 (2)2.65 (2)3.252 (2)135 (2)
N4—H3···Br10.78 (2)2.66 (2)3.0851 (15)115.8 (19)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+1, z; (iii) x1/2, y1/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds