N-(4-Chloro­phen­yl)-4-(pyrimidin-2-yl)piperazine-1-carboxamide

Li, Y.-F.

doi:10.1107/S160053681103515X

N-(4-Chlorophenyl)-4-(pyrimidin-2-yl)piperazine-1-carboxamide

The title compound, C₁₅H₁₆ClN₅O, contains two molecules, A and B, in the asymmetric unit, in which the dihedral angles between the terminal aromatic rings are 42.41 (17) and 45.77 (18)°. The central six-membered ring in both molecules has a chair conformation with equatorial substituents. In the crystal, molecules are linked into [100] C(4) chains of alternating A and B molecules by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681103515X/hb6389sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681103515X/hb6389Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S160053681103515X/hb6389Isup3.cml Supplementary material

CCDC reference: 850503

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.058
wR factor = 0.223
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X       H3AA   ..  H8AA    ..       1.82 Ang.
PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) .....         11

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0049 Ang
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         11

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.13
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         24
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The crystal structure of the title compound is presented herein. The molecular structure of the title compound is shown in Fig. 1. The six-membered rings (N4A, N5A, C5A, C6A, C7A, C8A) (N4B, N5B, C5B, C6B, C7B, C8B) are in chair conformations. The structures of related compound have already been determined Li (2011a,b).

Related literature top

For related structures, see: Li (2011a,b).

Experimental top

A mixture of 2-(piperazin-1-yl)pyrimidine (0.05 mol), and (4-chlorophenyl)carbamic chloride (0.05 mol) was stirred in refluxing ethanol (15 ml) for 6 h to afford the title compound (0.04 mol, yield 80%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Structure description top

For related structures, see: Li (2011a,b).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.

N-(4-Chlorophenyl)-4-(pyrimidin-2-yl)piperazine-1-carboxamide top

Crystal data top

C₁₅H₁₆ClN₅O	F(000) = 1328
M_r = 317.78	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3210 reflections
a = 9.992 (2) Å	θ = 3.1–26.9°
b = 9.978 (2) Å	µ = 0.26 mm⁻¹
c = 31.197 (6) Å	T = 293 K
β = 92.50 (3)°	Block, colorless
V = 3107.3 (11) Å³	0.22 × 0.21 × 0.19 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
φ and ω scans	h = −12→12
29790 measured reflections	k = −12→12
7075 independent reflections	l = −40→40

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.223	w = 1/[σ²(F_o²) + (0.1316P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
7075 reflections	Δρ_max = 0.31 e Å⁻³
398 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (14)

Crystal data top

C₁₅H₁₆ClN₅O	V = 3107.3 (11) Å³
M_r = 317.78	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.992 (2) Å	µ = 0.26 mm⁻¹
b = 9.978 (2) Å	T = 293 K
c = 31.197 (6) Å	0.22 × 0.21 × 0.19 mm
β = 92.50 (3)°

Data collection top

Bruker SMART CCD diffractometer	3210 reflections with I > 2σ(I)
29790 measured reflections	R_int = 0.070
7075 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.223	H-atom parameters constrained
S = 0.93	Δρ_max = 0.31 e Å⁻³
7075 reflections	Δρ_min = −0.35 e Å⁻³
398 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
Cl1A	0.63361 (12)	0.48186 (12)	0.04864 (3)	0.0889 (4)
Cl1B	0.29934 (11)	0.41025 (14)	0.44307 (3)	0.0920 (4)
O1B	0.02837 (19)	0.2901 (2)	0.24124 (7)	0.0555 (6)
O1A	0.51755 (19)	0.1666 (3)	0.23043 (7)	0.0644 (7)
N3B	0.2439 (2)	0.2371 (3)	0.26209 (8)	0.0507 (7)
H3BA	0.3181	0.2098	0.2521	0.061*
N5B	0.1716 (2)	−0.0057 (3)	0.12470 (8)	0.0521 (7)
C10B	0.2507 (3)	0.2866 (3)	0.30407 (9)	0.0454 (7)
N4A	0.6814 (2)	0.1119 (3)	0.27995 (9)	0.0552 (7)
C9A	0.6367 (3)	0.1683 (3)	0.24220 (10)	0.0507 (8)
N3A	0.7298 (2)	0.2315 (3)	0.21896 (8)	0.0560 (7)
H3AA	0.8101	0.2368	0.2299	0.067*
C9B	0.1331 (3)	0.2269 (3)	0.23506 (9)	0.0470 (7)
N2B	0.1097 (3)	−0.0434 (3)	0.05334 (8)	0.0589 (7)
N4B	0.1467 (2)	0.1485 (3)	0.20004 (8)	0.0527 (7)
N5A	0.7610 (3)	0.0069 (3)	0.36110 (9)	0.0636 (8)
C15B	0.1393 (3)	0.3037 (3)	0.32880 (10)	0.0557 (8)
H15A	0.0539	0.2894	0.3167	0.067*
C4B	0.1935 (3)	−0.0696 (3)	0.08677 (10)	0.0500 (8)
N2A	0.7043 (3)	−0.1024 (3)	0.42290 (9)	0.0676 (8)
C14B	0.1551 (3)	0.3419 (4)	0.37141 (11)	0.0608 (9)
H14A	0.0802	0.3530	0.3877	0.073*
C6A	0.5937 (3)	0.0212 (4)	0.30213 (11)	0.0606 (9)
H6AA	0.6087	−0.0700	0.2927	0.073*
H6AB	0.5010	0.0441	0.2951	0.073*
C12B	0.3911 (3)	0.3483 (4)	0.36561 (10)	0.0590 (9)
H12A	0.4761	0.3635	0.3780	0.071*
C15A	0.6295 (3)	0.2246 (4)	0.14602 (11)	0.0588 (8)
H15B	0.5926	0.1411	0.1515	0.071*
N1B	0.2941 (3)	−0.1586 (3)	0.08730 (9)	0.0700 (9)
C8B	0.2786 (3)	−0.0038 (4)	0.15814 (11)	0.0631 (9)
H8BA	0.3438	0.0642	0.1514	0.076*
H8BB	0.3238	−0.0899	0.1589	0.076*
C11A	0.7593 (3)	0.4140 (4)	0.16934 (11)	0.0602 (9)
H11A	0.8095	0.4587	0.1907	0.072*
C10A	0.7036 (3)	0.2897 (3)	0.17782 (10)	0.0517 (8)
N1A	0.9289 (3)	−0.0319 (3)	0.41271 (10)	0.0712 (9)
C4A	0.7992 (3)	−0.0428 (3)	0.40047 (11)	0.0575 (8)
C6B	0.0374 (3)	0.1454 (4)	0.16727 (10)	0.0597 (9)
H6BA	−0.0082	0.2312	0.1665	0.072*
H6BB	−0.0269	0.0771	0.1745	0.072*
C13B	0.2796 (3)	0.3633 (4)	0.38956 (10)	0.0581 (8)
C11B	0.3761 (3)	0.3107 (3)	0.32327 (10)	0.0542 (8)
H11B	0.4516	0.3013	0.3072	0.065*
C14A	0.6097 (3)	0.2824 (4)	0.10616 (11)	0.0639 (9)
H14B	0.5594	0.2384	0.0847	0.077*
C12A	0.7404 (4)	0.4714 (4)	0.12927 (13)	0.0668 (10)
H12B	0.7786	0.5540	0.1234	0.080*
C8A	0.8233 (3)	0.0853 (4)	0.29136 (12)	0.0640 (10)
H8AA	0.8788	0.1497	0.2771	0.077*
H8AB	0.8469	−0.0036	0.2816	0.077*
C13A	0.6650 (3)	0.4057 (4)	0.09834 (11)	0.0612 (9)
C5A	0.6198 (3)	0.0302 (4)	0.34979 (11)	0.0652 (10)
H5AA	0.5941	0.1182	0.3597	0.078*
H5AB	0.5658	−0.0359	0.3639	0.078*
C7B	0.2247 (3)	0.0249 (4)	0.20118 (10)	0.0588 (9)
H7BA	0.1684	−0.0490	0.2096	0.071*
H7BB	0.2983	0.0331	0.2223	0.071*
C7A	0.8498 (3)	0.0948 (4)	0.33886 (12)	0.0634 (9)
H7AA	0.9420	0.0703	0.3459	0.076*
H7AB	0.8366	0.1865	0.3481	0.076*
C5B	0.0904 (3)	0.1158 (4)	0.12395 (10)	0.0599 (9)
H5BA	0.0159	0.1053	0.1032	0.072*
H5BB	0.1442	0.1907	0.1149	0.072*
C2B	0.2315 (4)	−0.2037 (5)	0.01431 (12)	0.0776 (12)
H2BB	0.2456	−0.2495	−0.0111	0.093*
C3A	0.7452 (4)	−0.1557 (4)	0.46014 (12)	0.0749 (11)
H3AB	0.6819	−0.1974	0.4766	0.090*
C3B	0.3093 (4)	−0.2242 (4)	0.05043 (12)	0.0782 (12)
H3BB	0.3773	−0.2877	0.0495	0.094*
C1B	0.1308 (4)	−0.1113 (4)	0.01751 (11)	0.0706 (10)
H1BB	0.0746	−0.0952	−0.0065	0.085*
C2A	0.8744 (4)	−0.1528 (5)	0.47566 (12)	0.0827 (12)
H2AB	0.9009	−0.1918	0.5018	0.099*
C1A	0.9632 (4)	−0.0888 (5)	0.45040 (13)	0.0818 (12)
H1AB	1.0525	−0.0847	0.4600	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.0949 (8)	0.1019 (9)	0.0713 (6)	0.0216 (6)	0.0196 (6)	0.0231 (6)
Cl1B	0.0939 (8)	0.1238 (10)	0.0581 (6)	0.0002 (7)	0.0017 (5)	−0.0239 (6)
O1B	0.0418 (11)	0.0642 (15)	0.0604 (13)	0.0035 (10)	0.0026 (10)	−0.0023 (11)
O1A	0.0386 (11)	0.0899 (19)	0.0650 (14)	−0.0018 (11)	0.0045 (10)	0.0005 (12)
N3B	0.0339 (11)	0.0680 (19)	0.0502 (14)	−0.0014 (12)	0.0025 (11)	−0.0088 (13)
N5B	0.0467 (13)	0.0621 (18)	0.0471 (14)	0.0123 (12)	−0.0037 (11)	−0.0020 (12)
C10B	0.0389 (14)	0.0457 (18)	0.0517 (17)	−0.0001 (12)	0.0028 (13)	0.0005 (13)
N4A	0.0373 (12)	0.0663 (19)	0.0624 (17)	−0.0059 (12)	0.0064 (12)	0.0069 (14)
C9A	0.0434 (16)	0.055 (2)	0.0547 (18)	0.0007 (14)	0.0103 (14)	−0.0036 (14)
N3A	0.0396 (12)	0.070 (2)	0.0583 (16)	−0.0062 (12)	0.0037 (12)	0.0046 (14)
C9B	0.0385 (14)	0.052 (2)	0.0503 (16)	−0.0029 (13)	0.0045 (13)	0.0051 (14)
N2B	0.0588 (15)	0.068 (2)	0.0490 (15)	0.0095 (14)	−0.0062 (13)	−0.0030 (13)
N4B	0.0517 (14)	0.0561 (18)	0.0495 (14)	0.0120 (12)	−0.0087 (12)	−0.0054 (12)
N5A	0.0435 (14)	0.078 (2)	0.0695 (19)	−0.0052 (13)	0.0042 (13)	0.0220 (15)
C15B	0.0386 (14)	0.068 (2)	0.060 (2)	0.0003 (14)	0.0005 (14)	−0.0053 (16)
C4B	0.0419 (15)	0.060 (2)	0.0479 (17)	0.0014 (14)	−0.0001 (13)	−0.0021 (14)
N2A	0.0609 (17)	0.079 (2)	0.0631 (18)	0.0012 (15)	0.0086 (15)	0.0121 (16)
C14B	0.0476 (17)	0.076 (3)	0.059 (2)	0.0061 (16)	0.0079 (15)	−0.0070 (17)
C6A	0.0465 (16)	0.062 (2)	0.074 (2)	−0.0094 (15)	0.0109 (16)	0.0070 (17)
C12B	0.0430 (15)	0.076 (3)	0.0575 (19)	−0.0034 (16)	−0.0033 (15)	−0.0061 (17)
C15A	0.0574 (18)	0.052 (2)	0.067 (2)	−0.0098 (16)	0.0040 (17)	−0.0018 (16)
N1B	0.0608 (16)	0.088 (2)	0.0605 (17)	0.0213 (16)	−0.0051 (14)	−0.0158 (16)
C8B	0.0472 (17)	0.080 (3)	0.061 (2)	0.0148 (16)	−0.0105 (15)	−0.0096 (17)
C11A	0.0569 (18)	0.056 (2)	0.068 (2)	−0.0057 (16)	0.0055 (17)	−0.0028 (17)
C10A	0.0410 (14)	0.054 (2)	0.0603 (19)	0.0014 (14)	0.0073 (14)	−0.0001 (15)
N1A	0.0554 (17)	0.084 (2)	0.073 (2)	−0.0001 (15)	−0.0067 (15)	0.0107 (17)
C4A	0.0529 (18)	0.056 (2)	0.064 (2)	0.0016 (16)	0.0052 (16)	0.0032 (16)
C6B	0.0459 (16)	0.074 (3)	0.0585 (19)	0.0134 (16)	−0.0086 (15)	−0.0088 (17)
C13B	0.0606 (19)	0.058 (2)	0.0557 (19)	0.0054 (16)	0.0009 (16)	−0.0051 (15)
C11B	0.0397 (15)	0.069 (2)	0.0540 (18)	−0.0037 (14)	0.0040 (14)	−0.0083 (15)
C14A	0.0631 (19)	0.067 (3)	0.061 (2)	−0.0013 (18)	0.0019 (17)	−0.0066 (17)
C12A	0.066 (2)	0.058 (2)	0.078 (2)	−0.0060 (18)	0.017 (2)	0.0043 (19)
C8A	0.0411 (16)	0.072 (3)	0.080 (2)	−0.0002 (16)	0.0097 (17)	0.0142 (19)
C13A	0.0574 (18)	0.063 (2)	0.064 (2)	0.0114 (17)	0.0162 (17)	0.0040 (17)
C5A	0.0439 (16)	0.082 (3)	0.070 (2)	−0.0039 (17)	0.0027 (16)	0.0152 (19)
C7B	0.0584 (18)	0.059 (2)	0.0578 (19)	0.0166 (16)	−0.0126 (15)	−0.0052 (16)
C7A	0.0417 (16)	0.069 (2)	0.080 (2)	−0.0091 (16)	0.0011 (16)	0.0175 (19)
C5B	0.0575 (18)	0.066 (2)	0.0557 (19)	0.0161 (17)	−0.0046 (15)	−0.0018 (16)
C2B	0.082 (2)	0.093 (3)	0.057 (2)	0.017 (2)	−0.004 (2)	−0.018 (2)
C3A	0.080 (2)	0.090 (3)	0.055 (2)	0.002 (2)	0.0078 (19)	0.0073 (19)
C3B	0.071 (2)	0.091 (3)	0.072 (2)	0.026 (2)	−0.002 (2)	−0.022 (2)
C1B	0.078 (2)	0.079 (3)	0.0531 (19)	0.009 (2)	−0.0061 (18)	−0.0083 (18)
C2A	0.093 (3)	0.099 (4)	0.055 (2)	0.012 (3)	−0.008 (2)	0.006 (2)
C1A	0.070 (2)	0.104 (4)	0.070 (2)	0.005 (2)	−0.009 (2)	0.004 (2)

Geometric parameters (Å, º) top

Cl1A—C13A	1.743 (4)	C15A—C14A	1.377 (5)
Cl1B—C13B	1.737 (3)	C15A—H15B	0.9300
O1B—C9B	1.244 (3)	N1B—C3B	1.338 (4)
O1A—C9A	1.230 (4)	C8B—C7B	1.496 (5)
N3B—C9B	1.366 (4)	C8B—H8BA	0.9700
N3B—C10B	1.399 (4)	C8B—H8BB	0.9700
N3B—H3BA	0.8600	C11A—C12A	1.380 (5)
N5B—C4B	1.370 (4)	C11A—C10A	1.390 (5)
N5B—C5B	1.458 (4)	C11A—H11A	0.9300
N5B—C8B	1.461 (4)	N1A—C1A	1.337 (5)
C10B—C11B	1.385 (4)	N1A—C4A	1.340 (4)
C10B—C15B	1.392 (4)	C6B—C5B	1.502 (4)
N4A—C9A	1.363 (4)	C6B—H6BA	0.9700
N4A—C6A	1.456 (4)	C6B—H6BB	0.9700
N4A—C8A	1.471 (4)	C11B—H11B	0.9300
C9A—N3A	1.360 (4)	C14A—C13A	1.375 (5)
N3A—C10A	1.422 (4)	C14A—H14B	0.9300
N3A—H3AA	0.8600	C12A—C13A	1.365 (5)
C9B—N4B	1.356 (4)	C12A—H12B	0.9300
N2B—C1B	1.332 (4)	C8A—C7A	1.497 (5)
N2B—C4B	1.334 (4)	C8A—H8AA	0.9700
N4B—C7B	1.458 (4)	C8A—H8AB	0.9700
N4B—C6B	1.463 (4)	C5A—H5AA	0.9700
N5A—C4A	1.364 (4)	C5A—H5AB	0.9700
N5A—C7A	1.446 (4)	C7B—H7BA	0.9700
N5A—C5A	1.458 (4)	C7B—H7BB	0.9700
C15B—C14B	1.385 (4)	C7A—H7AA	0.9700
C15B—H15A	0.9300	C7A—H7AB	0.9700
C4B—N1B	1.341 (4)	C5B—H5BA	0.9700
N2A—C3A	1.326 (5)	C5B—H5BB	0.9700
N2A—C4A	1.342 (4)	C2B—C3B	1.356 (5)
C14B—C13B	1.360 (5)	C2B—C1B	1.372 (5)
C14B—H14A	0.9300	C2B—H2BB	0.9300
C6A—C5A	1.501 (5)	C3A—C2A	1.359 (5)
C6A—H6AA	0.9700	C3A—H3AB	0.9300
C6A—H6AB	0.9700	C3B—H3BB	0.9300
C12B—C11B	1.375 (4)	C1B—H1BB	0.9300
C12B—C13B	1.377 (4)	C2A—C1A	1.370 (6)
C12B—H12A	0.9300	C2A—H2AB	0.9300
C15A—C10A	1.375 (5)	C1A—H1AB	0.9300

C9B—N3B—C10B	127.5 (2)	N4B—C6B—H6BA	109.5
C9B—N3B—H3BA	116.2	C5B—C6B—H6BA	109.5
C10B—N3B—H3BA	116.2	N4B—C6B—H6BB	109.5
C4B—N5B—C5B	118.9 (3)	C5B—C6B—H6BB	109.5
C4B—N5B—C8B	118.9 (2)	H6BA—C6B—H6BB	108.1
C5B—N5B—C8B	113.0 (3)	C14B—C13B—C12B	120.3 (3)
C11B—C10B—C15B	117.9 (3)	C14B—C13B—Cl1B	120.4 (2)
C11B—C10B—N3B	118.2 (2)	C12B—C13B—Cl1B	119.3 (3)
C15B—C10B—N3B	123.7 (3)	C12B—C11B—C10B	121.4 (3)
C9A—N4A—C6A	119.0 (3)	C12B—C11B—H11B	119.3
C9A—N4A—C8A	124.1 (2)	C10B—C11B—H11B	119.3
C6A—N4A—C8A	111.5 (3)	C13A—C14A—C15A	119.5 (4)
O1A—C9A—N3A	121.5 (3)	C13A—C14A—H14B	120.3
O1A—C9A—N4A	122.0 (3)	C15A—C14A—H14B	120.3
N3A—C9A—N4A	116.5 (3)	C13A—C12A—C11A	119.4 (4)
C9A—N3A—C10A	124.6 (3)	C13A—C12A—H12B	120.3
C9A—N3A—H3AA	117.7	C11A—C12A—H12B	120.3
C10A—N3A—H3AA	117.7	N4A—C8A—C7A	110.8 (3)
O1B—C9B—N4B	122.2 (3)	N4A—C8A—H8AA	109.5
O1B—C9B—N3B	122.1 (3)	C7A—C8A—H8AA	109.5
N4B—C9B—N3B	115.7 (3)	N4A—C8A—H8AB	109.5
C1B—N2B—C4B	116.1 (3)	C7A—C8A—H8AB	109.5
C9B—N4B—C7B	122.7 (3)	H8AA—C8A—H8AB	108.1
C9B—N4B—C6B	118.5 (2)	C12A—C13A—C14A	121.2 (4)
C7B—N4B—C6B	112.4 (3)	C12A—C13A—Cl1A	119.5 (3)
C4A—N5A—C7A	119.9 (3)	C14A—C13A—Cl1A	119.3 (3)
C4A—N5A—C5A	120.4 (3)	N5A—C5A—C6A	110.8 (3)
C7A—N5A—C5A	113.3 (3)	N5A—C5A—H5AA	109.5
C14B—C15B—C10B	120.3 (3)	C6A—C5A—H5AA	109.5
C14B—C15B—H15A	119.8	N5A—C5A—H5AB	109.5
C10B—C15B—H15A	119.8	C6A—C5A—H5AB	109.5
N2B—C4B—N1B	125.7 (3)	H5AA—C5A—H5AB	108.1
N2B—C4B—N5B	117.7 (3)	N4B—C7B—C8B	110.7 (3)
N1B—C4B—N5B	116.5 (3)	N4B—C7B—H7BA	109.5
C3A—N2A—C4A	115.9 (3)	C8B—C7B—H7BA	109.5
C13B—C14B—C15B	120.4 (3)	N4B—C7B—H7BB	109.5
C13B—C14B—H14A	119.8	C8B—C7B—H7BB	109.5
C15B—C14B—H14A	119.8	H7BA—C7B—H7BB	108.1
N4A—C6A—C5A	110.6 (3)	N5A—C7A—C8A	110.5 (3)
N4A—C6A—H6AA	109.5	N5A—C7A—H7AA	109.5
C5A—C6A—H6AA	109.5	C8A—C7A—H7AA	109.5
N4A—C6A—H6AB	109.5	N5A—C7A—H7AB	109.5
C5A—C6A—H6AB	109.5	C8A—C7A—H7AB	109.5
H6AA—C6A—H6AB	108.1	H7AA—C7A—H7AB	108.1
C11B—C12B—C13B	119.6 (3)	N5B—C5B—C6B	111.5 (3)
C11B—C12B—H12A	120.2	N5B—C5B—H5BA	109.3
C13B—C12B—H12A	120.2	C6B—C5B—H5BA	109.3
C10A—C15A—C14A	120.3 (3)	N5B—C5B—H5BB	109.3
C10A—C15A—H15B	119.8	C6B—C5B—H5BB	109.3
C14A—C15A—H15B	119.8	H5BA—C5B—H5BB	108.0
C3B—N1B—C4B	115.3 (3)	C3B—C2B—C1B	115.9 (3)
N5B—C8B—C7B	111.2 (3)	C3B—C2B—H2BB	122.1
N5B—C8B—H8BA	109.4	C1B—C2B—H2BB	122.1
C7B—C8B—H8BA	109.4	N2A—C3A—C2A	123.7 (4)
N5B—C8B—H8BB	109.4	N2A—C3A—H3AB	118.1
C7B—C8B—H8BB	109.4	C2A—C3A—H3AB	118.1
H8BA—C8B—H8BB	108.0	N1B—C3B—C2B	123.9 (4)
C12A—C11A—C10A	120.2 (4)	N1B—C3B—H3BB	118.0
C12A—C11A—H11A	119.9	C2B—C3B—H3BB	118.0
C10A—C11A—H11A	119.9	N2B—C1B—C2B	123.1 (4)
C15A—C10A—C11A	119.5 (3)	N2B—C1B—H1BB	118.4
C15A—C10A—N3A	122.0 (3)	C2B—C1B—H1BB	118.4
C11A—C10A—N3A	118.5 (3)	C3A—C2A—C1A	115.7 (4)
C1A—N1A—C4A	115.1 (3)	C3A—C2A—H2AB	122.2
N1A—C4A—N2A	125.7 (3)	C1A—C2A—H2AB	122.2
N1A—C4A—N5A	117.2 (3)	N1A—C1A—C2A	123.8 (4)
N2A—C4A—N5A	117.0 (3)	N1A—C1A—H1AB	118.1
N4B—C6B—C5B	110.6 (3)	C2A—C1A—H1AB	118.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3B—H3BA···O1A	0.86	2.18	3.030 (3)	172
N3A—H3AA···O1Bⁱ	0.86	2.26	3.090 (3)	163

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆ClN₅O
M_r	317.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.992 (2), 9.978 (2), 31.197 (6)
β (°)	92.50 (3)
V (Å³)	3107.3 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.22 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29790, 7075, 3210
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.223, 0.93
No. of reflections	7075
No. of parameters	398
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).