4-Amino-2-chloro-5-nitro-6-(propyl­amino)­pyrimidine

McKeveney, D.; Quinn, R.J.; Janssen, C.O.; Healy, P.C.

doi:10.1107/S1600536804015028

4-Amino-2-chloro-5-nitro-6-(propylamino)pyrimidine

D. McKeveney, R. J. Quinn, C. O. Janssen and P. C. Healy

The title compound, C₇H₁₀ClN₅O₂, was synthesized as part of a study to demonstrate the reactivity of 4-amino-2,6-dichloro-5-nitropyrimidine with respect to various amine substitutions. The structure determination allowed unambiguous assignment of the regioselectivity of the substitution of the propylamine group at the 6-position. Intra- and intermolecular N—H

O and N—H

N hydrogen bonding yields polymeric chains of coplanar molecules. There are two independent molecules in the asymmetric unit.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015028/tk6175sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015028/tk6175Isup2.hkl Contains datablock I

CCDC reference: 245337

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.007 Å
R factor = 0.050
wR factor = 0.158
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C8A
PLAT430_ALERT_2_B Short Inter D...A Contact  O52A   ..  O52B    ..       2.79 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.81 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C7A    -   C8A    ...       1.39 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H10 Cl N5 O2

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC7 Diffractometer Control for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

4-amino-2-chloro-5-nitro-6-(propylamino)pyrimidine top

Crystal data top

C₇H₁₀ClN₅O₂	Z = 4
M_r = 231.65	F(000) = 480
Triclinic, P1	D_x = 1.518 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.406 (3) Å	Cell parameters from 25 reflections
b = 11.074 (3) Å	θ = 12.7–17.4°
c = 13.886 (5) Å	µ = 0.37 mm⁻¹
α = 112.54 (2)°	T = 295 K
β = 94.82 (3)°	Prismatic, colourless
γ = 101.69 (3)°	0.30 × 0.15 × 0.10 mm
V = 1013.4 (7) Å³

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.025
Radiation source: Rigaku rotating anode	θ_max = 25.0°, θ_min = 2.9°
Graphite monochromator	h = −8→8
ω/2θ scans	k = −12→13
3994 measured reflections	l = −16→7
3565 independent reflections	3 standard reflections every 150 reflections
1948 reflections with I > 2σ(I)	intensity decay: 2.9%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0687P)² + 0.5417P] where P = (F_o² + 2F_c²)/3
3565 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Special details top

Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 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 > 2σ(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

	x	y	z	U_iso*/U_eq
Cl2A	0.85919 (17)	0.63673 (11)	−0.14901 (8)	0.0599 (4)
O51A	0.6980 (5)	1.1475 (3)	0.2298 (2)	0.0765 (13)
O52A	0.7044 (5)	1.0156 (3)	0.3078 (2)	0.0682 (13)
N1A	0.8053 (4)	0.7210 (3)	0.0437 (2)	0.0426 (11)
N3A	0.7873 (4)	0.8650 (3)	−0.0461 (2)	0.0402 (11)
N4A	0.7342 (5)	1.0719 (3)	0.0316 (2)	0.0456 (11)
N5A	0.7155 (5)	1.0389 (3)	0.2282 (2)	0.0487 (11)
N6A	0.7698 (5)	0.7796 (3)	0.2153 (3)	0.0529 (12)
C2A	0.8111 (5)	0.7556 (4)	−0.0362 (3)	0.0400 (12)
C4A	0.7550 (5)	0.9617 (3)	0.0419 (3)	0.0362 (11)
C5A	0.7471 (5)	0.9392 (3)	0.1364 (3)	0.0367 (11)
C6A	0.7731 (5)	0.8134 (4)	0.1334 (3)	0.0376 (12)
C7A	0.7962 (7)	0.6526 (5)	0.2142 (4)	0.0669 (19)
C8A	0.6349 (8)	0.5575 (5)	0.2073 (6)	0.107 (3)
C9A	0.6618 (7)	0.4321 (5)	0.2209 (5)	0.0747 (19)
Cl2B	0.71247 (16)	1.31999 (10)	0.92443 (8)	0.0561 (4)
O51B	0.8335 (5)	0.7953 (3)	0.5424 (2)	0.0654 (13)
O52B	0.7897 (5)	0.9143 (3)	0.4564 (2)	0.0665 (13)
N1B	0.7114 (5)	1.2186 (3)	0.7236 (2)	0.0459 (11)
N3B	0.7534 (4)	1.0825 (3)	0.8182 (2)	0.0412 (10)
N4B	0.7995 (5)	0.8737 (3)	0.7410 (2)	0.0496 (13)
N5B	0.7986 (5)	0.8988 (3)	0.5403 (2)	0.0465 (11)
N6B	0.7112 (5)	1.1461 (3)	0.5460 (3)	0.0574 (14)
C2B	0.7274 (5)	1.1912 (4)	0.8077 (3)	0.0390 (12)
C4B	0.7739 (5)	0.9823 (3)	0.7289 (3)	0.0367 (12)
C5B	0.7690 (5)	0.9997 (3)	0.6325 (3)	0.0390 (11)
C6B	0.7300 (5)	1.1216 (4)	0.6319 (3)	0.0425 (14)
C7B	0.6626 (7)	1.2670 (5)	0.5430 (4)	0.0645 (19)
C8B	0.8261 (8)	1.3790 (6)	0.5757 (5)	0.083 (2)
C9B	0.7722 (10)	1.5016 (5)	0.5612 (5)	0.103 (3)
H6A	0.75000	0.84290	0.28030	0.0420*
H41A	0.71120	1.14410	0.08980	0.0550*
H42A	0.74220	1.07920	−0.03400	0.0550*
H71A	0.87790	0.67270	0.27800	0.0810*
H72A	0.85390	0.61300	0.15540	0.0810*
H81A	0.56820	0.60120	0.25970	0.1270*
H82A	0.56150	0.52810	0.13880	0.1270*
H91A	0.74280	0.39310	0.17570	0.0900*
H92A	0.54390	0.36860	0.20360	0.0900*
H93A	0.71550	0.45680	0.29260	0.0900*
H6B	0.73060	1.08110	0.48190	0.0690*
H41B	0.81510	0.79900	0.68210	0.0600*
H42B	0.80230	0.87050	0.80840	0.0600*
H71B	0.57590	1.29160	0.58920	0.0770*
H72B	0.60650	1.24690	0.47270	0.0770*
H81B	0.87570	1.40520	0.64820	0.1000*
H82B	0.91770	1.35220	0.53390	0.1000*
H91B	0.87450	1.57970	0.59450	0.1230*
H92B	0.66580	1.51830	0.59260	0.1230*
H93B	0.74450	1.48140	0.48780	0.1230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2A	0.0822 (8)	0.0499 (6)	0.0463 (6)	0.0271 (6)	0.0233 (6)	0.0107 (5)
O51A	0.149 (3)	0.0454 (18)	0.058 (2)	0.049 (2)	0.050 (2)	0.0270 (16)
O52A	0.124 (3)	0.0585 (19)	0.0359 (16)	0.0355 (18)	0.0303 (17)	0.0245 (15)
N1A	0.055 (2)	0.0366 (18)	0.0426 (18)	0.0172 (15)	0.0128 (15)	0.0195 (15)
N3A	0.052 (2)	0.0407 (18)	0.0333 (17)	0.0162 (15)	0.0122 (14)	0.0179 (14)
N4A	0.069 (2)	0.0426 (18)	0.0403 (18)	0.0243 (16)	0.0204 (16)	0.0258 (15)
N5A	0.071 (2)	0.044 (2)	0.0355 (18)	0.0178 (17)	0.0188 (16)	0.0174 (16)
N6A	0.076 (2)	0.052 (2)	0.049 (2)	0.0286 (18)	0.0220 (18)	0.0319 (17)
C2A	0.042 (2)	0.041 (2)	0.037 (2)	0.0110 (17)	0.0107 (17)	0.0150 (17)
C4A	0.038 (2)	0.036 (2)	0.0338 (19)	0.0076 (16)	0.0077 (16)	0.0141 (16)
C5A	0.050 (2)	0.0344 (19)	0.0287 (18)	0.0132 (17)	0.0116 (16)	0.0138 (15)
C6A	0.039 (2)	0.037 (2)	0.038 (2)	0.0091 (16)	0.0061 (16)	0.0170 (17)
C7A	0.087 (4)	0.070 (3)	0.084 (3)	0.044 (3)	0.036 (3)	0.058 (3)
C8A	0.073 (4)	0.056 (3)	0.222 (8)	0.033 (3)	0.060 (4)	0.075 (4)
C9A	0.069 (3)	0.053 (3)	0.111 (4)	0.021 (2)	0.017 (3)	0.040 (3)
Cl2B	0.0817 (8)	0.0481 (6)	0.0375 (6)	0.0287 (5)	0.0156 (5)	0.0095 (5)
O51B	0.118 (3)	0.0478 (17)	0.0494 (17)	0.0477 (18)	0.0305 (17)	0.0235 (15)
O52B	0.121 (3)	0.0571 (19)	0.0324 (15)	0.0367 (18)	0.0251 (16)	0.0206 (14)
N1B	0.067 (2)	0.0386 (18)	0.0394 (18)	0.0197 (16)	0.0199 (16)	0.0184 (15)
N3B	0.058 (2)	0.0372 (17)	0.0346 (17)	0.0164 (15)	0.0128 (15)	0.0182 (14)
N4B	0.082 (3)	0.0393 (18)	0.0379 (18)	0.0255 (17)	0.0168 (17)	0.0205 (15)
N5B	0.069 (2)	0.0405 (19)	0.0344 (18)	0.0185 (17)	0.0148 (16)	0.0166 (15)
N6B	0.103 (3)	0.051 (2)	0.0413 (19)	0.041 (2)	0.0276 (19)	0.0296 (17)
C2B	0.047 (2)	0.039 (2)	0.032 (2)	0.0150 (17)	0.0104 (17)	0.0129 (17)
C4B	0.043 (2)	0.035 (2)	0.035 (2)	0.0095 (17)	0.0089 (16)	0.0174 (17)
C5B	0.054 (2)	0.0327 (19)	0.034 (2)	0.0107 (17)	0.0128 (17)	0.0167 (16)
C6B	0.056 (3)	0.040 (2)	0.039 (2)	0.0170 (19)	0.0127 (19)	0.0209 (18)
C7B	0.091 (4)	0.060 (3)	0.058 (3)	0.032 (3)	0.025 (3)	0.032 (2)
C8B	0.099 (4)	0.071 (3)	0.094 (4)	0.035 (3)	0.041 (3)	0.038 (3)
C9B	0.170 (6)	0.059 (3)	0.115 (5)	0.050 (4)	0.065 (5)	0.054 (3)

Geometric parameters (Å, º) top

Cl2A—C2A	1.738 (4)	N4B—H41B	0.9505
Cl2B—C2B	1.732 (4)	N4B—H42B	0.9487
O51A—N5A	1.228 (5)	N6B—H6B	0.9508
O52A—N5A	1.233 (4)	C4A—C5A	1.430 (5)
O51B—N5B	1.235 (5)	C5A—C6A	1.430 (6)
O52B—N5B	1.239 (4)	C7A—C8A	1.392 (8)
N1A—C2A	1.306 (5)	C8A—C9A	1.520 (9)
N1A—C6A	1.352 (5)	C7A—H72A	0.9498
N3A—C4A	1.360 (5)	C7A—H71A	0.9513
N3A—C2A	1.314 (6)	C8A—H81A	0.9463
N4A—C4A	1.319 (5)	C8A—H82A	0.9543
N5A—C5A	1.406 (5)	C9A—H92A	0.9493
N6A—C6A	1.327 (6)	C9A—H93A	0.9514
N6A—C7A	1.453 (7)	C9A—H91A	0.9493
N4A—H42A	0.9504	C4B—C5B	1.422 (5)
N4A—H41A	0.9514	C5B—C6B	1.439 (6)
N6A—H6A	0.9525	C7B—C8B	1.442 (9)
N1B—C2B	1.316 (5)	C8B—C9B	1.568 (9)
N1B—C6B	1.355 (5)	C7B—H71B	0.9510
N3B—C2B	1.316 (6)	C7B—H72B	0.9504
N3B—C4B	1.356 (5)	C8B—H81B	0.9507
N4B—C4B	1.324 (5)	C8B—H82B	0.9493
N5B—C5B	1.410 (5)	C9B—H91B	0.9515
N6B—C6B	1.323 (6)	C9B—H92B	0.9489
N6B—C7B	1.469 (7)	C9B—H93B	0.9501

Cl2B···C6Aⁱ	3.495 (4)	C6A···N3B^ix	3.384 (5)
Cl2A···H42Bⁱⁱ	2.9666	C6A···C4B^ix	3.545 (6)
Cl2A···H81Bⁱⁱⁱ	3.0294	C7B···N5Bⁱ	3.398 (7)
Cl2A···H92A^iv	3.0007	C8B···N1B	3.251 (8)
Cl2A···H91A^v	3.0691	C9A···O51A^viii	3.264 (7)
Cl2B···H42A^vi	2.9810	C9B···O51B^vii	3.305 (7)
O51A···N4A	2.607 (4)	C2A···H42Bⁱⁱ	2.8968
O51A···C9A^vii	3.264 (7)	C2A···H92A^iv	3.0443
O51B···N4B	2.607 (4)	C2B···H42A^vi	2.9126
O51B···C9B^viii	3.305 (7)	C4A···H42Bⁱⁱ	3.0796
O52A···C2Bⁱ	3.377 (5)	C4B···H42A^vi	3.0942
O52A···O52B	2.785 (5)	C6B···H81B	3.0200
O52A···N6A	2.601 (5)	C9B···H41B^vii	3.0034
O52A···N6B	3.052 (5)	H6A···O52B	2.2353
O52B···O52B^ix	3.160 (5)	H6A···N5A	2.5875
O52B···O52A	2.785 (5)	H6A···O52A	1.9084
O52B···N6A	3.076 (5)	H6B···O52A	2.2204
O52B···N6B	2.599 (5)	H6B···O52B	1.8926
O51A···H41A	1.9410	H6B···N5B	2.5658
O51B···H82B^ix	2.7219	H41A···N5A	2.6019
O51B···H41B	1.9414	H41A···H91A^vii	2.5010
O51B···H91B^viii	2.8098	H41A···O51A	1.9410
O52A···H6B	2.2204	H41B···O51B	1.9414
O52A···H6A	1.9084	H41B···N5B	2.6064
O52B···H6A	2.2353	H41B···C9B^viii	3.0034
O52B···H6B	1.8926	H41B···H91B^viii	2.4151
N1B···C8B	3.251 (8)	H42A···Cl2Bⁱⁱ	2.9810
N3A···N4Bⁱⁱ	3.003 (4)	H42A···N3Bⁱⁱ	2.0749
N3B···C6A^ix	3.384 (5)	H42A···C2Bⁱⁱ	2.9126
N3B···N4A^vi	3.024 (4)	H42A···C4Bⁱⁱ	3.0942
N4A···N5A	2.900 (4)	H42B···C4A^vi	3.0796
N4A···O51A	2.607 (4)	H42B···Cl2A^vi	2.9666
N4A···N3Bⁱⁱ	3.024 (4)	H42B···N3A^vi	2.0560
N4B···N3A^vi	3.003 (4)	H42B···C2A^vi	2.8968
N4B···N5B	2.904 (4)	H71A···H81B^ix	2.4748
N4B···O51B	2.607 (4)	H71A···H93A	2.5398
N5A···N6A	2.920 (5)	H71B···H81Aⁱ	2.4359
N5A···N4A	2.900 (4)	H71B···H92B	2.4443
N5B···N4B	2.904 (4)	H71B···N1B	2.5124
N5B···N6B	2.913 (5)	H72A···H91A	2.5375
N5B···C7Bⁱ	3.398 (7)	H72A···N1A	2.3380
N6A···O52A	2.601 (5)	H72B···H93B	2.5108
N6A···O52B	3.076 (5)	H81A···H71Bⁱ	2.4360
N6A···N5A	2.920 (5)	H81B···C6B	3.0200
N6B···N5B	2.913 (5)	H81B···N1B	2.7745
N6B···O52A	3.052 (5)	H81B···H71A^ix	2.4748
N6B···O52B	2.599 (5)	H81B···Cl2A^x	3.0294
N1A···H72A	2.3380	H82B···O51B^ix	2.7219
N1B···H81B	2.7745	H91A···H72A	2.5375
N1B···H71B	2.5124	H91A···H41A^viii	2.5010
N3A···H42Bⁱⁱ	2.0560	H91A···Cl2A^v	3.0691
N3B···H42A^vi	2.0749	H91B···H41B^vii	2.4151
N5A···H41A	2.6019	H91B···O51B^vii	2.8098
N5A···H6A	2.5875	H92A···Cl2A^iv	3.0007
N5B···H6B	2.5658	H92A···C2A^iv	3.0443
N5B···H41B	2.6064	H92B···H71B	2.4443
C2B···O52Aⁱ	3.377 (6)	H93A···H71A	2.5398
C4B···C6A^ix	3.545 (6)	H93B···H72B	2.5108
C6A···Cl2Bⁱ	3.495 (4)

C2A—N1A—C6A	115.7 (4)	C7A—C8A—H82A	107.20
C2A—N3A—C4A	115.6 (3)	H81A—C8A—H82A	109.37
O51A—N5A—O52A	120.0 (3)	C9A—C8A—H82A	107.41
O51A—N5A—C5A	121.1 (3)	C7A—C8A—H81A	107.82
O52A—N5A—C5A	118.9 (3)	C9A—C8A—H81A	107.97
C6A—N6A—C7A	124.9 (4)	C8A—C9A—H92A	109.46
C4A—N4A—H42A	120.02	C8A—C9A—H93A	109.20
H41A—N4A—H42A	119.96	H91A—C9A—H92A	109.66
C4A—N4A—H41A	120.03	H91A—C9A—H93A	109.51
C6A—N6A—H6A	118.34	C8A—C9A—H91A	109.65
C7A—N6A—H6A	116.73	H92A—C9A—H93A	109.34
C2B—N1B—C6B	115.9 (4)	Cl2B—C2B—N1B	114.7 (3)
C2B—N3B—C4B	115.7 (3)	Cl2B—C2B—N3B	114.4 (3)
O51B—N5B—O52B	119.8 (3)	N1B—C2B—N3B	130.9 (4)
O52B—N5B—C5B	119.6 (3)	N4B—C4B—C5B	125.3 (3)
O51B—N5B—C5B	120.6 (3)	N3B—C4B—C5B	119.9 (3)
C6B—N6B—C7B	124.5 (4)	N3B—C4B—N4B	114.8 (3)
C4B—N4B—H42B	120.04	N5B—C5B—C4B	120.5 (3)
H41B—N4B—H42B	120.06	C4B—C5B—C6B	118.1 (3)
C4B—N4B—H41B	119.90	N5B—C5B—C6B	121.5 (3)
C6B—N6B—H6B	117.75	N1B—C6B—N6B	116.9 (4)
C7B—N6B—H6B	117.78	N6B—C6B—C5B	123.8 (4)
Cl2A—C2A—N1A	114.5 (3)	N1B—C6B—C5B	119.3 (4)
Cl2A—C2A—N3A	114.2 (3)	N6B—C7B—C8B	111.4 (5)
N1A—C2A—N3A	131.2 (4)	C7B—C8B—C9B	110.0 (5)
N3A—C4A—C5A	119.7 (3)	N6B—C7B—H71B	109.02
N3A—C4A—N4A	115.1 (3)	N6B—C7B—H72B	109.02
N4A—C4A—C5A	125.2 (3)	C8B—C7B—H71B	109.03
N5A—C5A—C4A	120.2 (3)	C8B—C7B—H72B	108.97
C4A—C5A—C6A	117.7 (3)	H71B—C7B—H72B	109.37
N5A—C5A—C6A	122.1 (3)	C7B—C8B—H81B	109.29
N6A—C6A—C5A	123.9 (4)	C7B—C8B—H82B	109.33
N1A—C6A—N6A	115.9 (4)	C9B—C8B—H81B	109.38
N1A—C6A—C5A	120.1 (4)	C9B—C8B—H82B	109.48
N6A—C7A—C8A	116.2 (5)	H81B—C8B—H82B	109.39
C7A—C8A—C9A	116.9 (5)	C8B—C9B—H91B	109.37
C8A—C7A—H72A	108.05	C8B—C9B—H92B	109.56
H71A—C7A—H72A	109.37	C8B—C9B—H93B	109.50
C8A—C7A—H71A	107.56	H91B—C9B—H92B	109.43
N6A—C7A—H71A	107.71	H91B—C9B—H93B	109.36
N6A—C7A—H72A	107.86	H92B—C9B—H93B	109.61

C6A—N1A—C2A—Cl2A	178.3 (3)	O51B—N5B—C5B—C4B	−1.7 (6)
C6A—N1A—C2A—N3A	−1.5 (6)	O52B—N5B—C5B—C4B	178.4 (4)
C2A—N1A—C6A—N6A	−179.0 (3)	O52B—N5B—C5B—C6B	−0.5 (6)
C2A—N1A—C6A—C5A	0.3 (5)	C7B—N6B—C6B—N1B	−3.3 (6)
C4A—N3A—C2A—Cl2A	−178.1 (3)	C7B—N6B—C6B—C5B	177.0 (4)
C4A—N3A—C2A—N1A	1.7 (6)	C6B—N6B—C7B—C8B	84.0 (6)
C2A—N3A—C4A—N4A	179.0 (3)	N3A—C4A—C5A—N5A	179.4 (3)
C2A—N3A—C4A—C5A	−0.6 (5)	N4A—C4A—C5A—N5A	−0.2 (6)
O51A—N5A—C5A—C4A	−1.5 (6)	N4A—C4A—C5A—C6A	−179.9 (4)
O51A—N5A—C5A—C6A	178.2 (4)	N3A—C4A—C5A—C6A	−0.3 (5)
O52A—N5A—C5A—C4A	178.1 (4)	C4A—C5A—C6A—N1A	0.5 (5)
O52A—N5A—C5A—C6A	−2.2 (6)	N5A—C5A—C6A—N1A	−179.2 (3)
C7A—N6A—C6A—N1A	−0.6 (6)	C4A—C5A—C6A—N6A	179.8 (4)
C7A—N6A—C6A—C5A	−179.9 (4)	N5A—C5A—C6A—N6A	0.0 (6)
C6A—N6A—C7A—C8A	−103.2 (6)	N6A—C7A—C8A—C9A	−172.0 (5)
C2B—N1B—C6B—N6B	178.9 (3)	N3B—C4B—C5B—N5B	177.1 (3)
C2B—N1B—C6B—C5B	−1.3 (5)	N4B—C4B—C5B—C6B	176.8 (4)
C6B—N1B—C2B—Cl2B	177.5 (3)	N3B—C4B—C5B—C6B	−3.9 (5)
C6B—N1B—C2B—N3B	−2.3 (6)	N4B—C4B—C5B—N5B	−2.1 (6)
C4B—N3B—C2B—Cl2B	−177.2 (3)	N5B—C5B—C6B—N6B	2.9 (6)
C4B—N3B—C2B—N1B	2.6 (6)	C4B—C5B—C6B—N1B	4.2 (5)
C2B—N3B—C4B—C5B	0.8 (5)	C4B—C5B—C6B—N6B	−176.0 (4)
C2B—N3B—C4B—N4B	−179.9 (3)	N5B—C5B—C6B—N1B	−176.9 (3)
O51B—N5B—C5B—C6B	179.4 (4)	N6B—C7B—C8B—C9B	174.6 (5)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z−1; (iii) x, y−1, z−1; (iv) −x+1, −y+1, −z; (v) −x+2, −y+1, −z; (vi) x, y, z+1; (vii) x, y+1, z; (viii) x, y−1, z; (ix) −x+2, −y+2, −z+1; (x) x, y+1, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6A—H6A···O52A	0.95	1.91	2.601 (5)	128
N6A—H6A···O52B	0.95	2.24	3.076 (5)	147
N6B—H6B···O52A	0.95	2.22	3.052 (5)	146
N6B—H6B···O52B	0.95	1.89	2.599 (5)	129
N4A—H41A···O51A	0.95	1.94	2.607 (4)	125
N4B—H41B···O51B	0.95	1.94	2.607 (4)	125
N4A—H42A···N3Bⁱⁱ	0.95	2.07	3.024 (4)	177
N4B—H42B···N3A^vi	0.95	2.06	3.003 (4)	176

Symmetry codes: (ii) x, y, z−1; (vi) x, y, z+1.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

4-Amino-2-chloro-5-nitro-6-(propyl­amino)­pyrimidine

Supporting information

Key indicators

checkCIF/PLATON results

4-Amino-2-chloro-5-nitro-6-(propylamino)pyrimidine