3-(4-Chloro­phen­yl)-2-(diisobutyl­amino)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

He, P.; Zheng, A.; Cai, C.-Q.; Fang, C.-L.

doi:10.1107/S1600536807028383

3-(4-Chlorophenyl)-2-(diisobutylamino)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

P. He, A. Zheng, C.-Q. Cai and C.-L. Fang

A tandem aza-Wittig reaction of ethyl 3-triphenylphosphoranylideneamino-4-cyano-1-phenyl-1H-pyrrole-2-carboxylate with 4-chlorophenyl isocyanate and diisobutylamine produced the title compound, C₂₇H₂₈ClN₅O. In the molecule, the angles between the fused-ring system and the two benzene rings are 51.66 (2) and 65.79 (2)°. Intramolecular C—H

N hydrogen bonds determine the conformation of the molecule. The packing of the molecules in the crystal structure is governed mainly by intermolecular C—H

N hydrogen-bonding interactions. There are no π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028383/wn2151sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028383/wn2151Isup2.hkl Contains datablock I

CCDC reference: 654934

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.064
wR factor = 0.169
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C11    ...       1.42 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            C7  -C8  -C11 -N2    156.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            C9  -C8  -C11 -N2    -22.00  9.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.40 Deg.
              C21' -C20  -C21     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.80 Deg.
              C20  -C21  -H20C    1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

Comment top

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Kondo et al., 1986; Bayomi et al., 1986; Ding et al., 2004). In recent years, we have been engaged in the preparation of derivatives of heterocycles using the aza-Wittig reaction. Some related X-ray crystal structure reports for pyrimidinone derivatives have been published (Zheng et al., 2006; Hu et al., 2005; Xu et al., 2005). Here, the structure of the title compound, which may be used as a new precursor for obtaining bioactive molecules, is reported (Fig. 1). The bond lengths and angles are unexceptional. Rings A (atoms N1/C7/C8/C9/C10), B (C9/C10/C12/N3/C13/N4), C (C1—C6), D (C14—C19) are, of course, planar and the dihedral angles between them are A/B = 2.80 (14)°, A/C = 51.66 (2)°, B/D = 65.79 (2)°. C21, C22, C23 and attached hydrogen atoms are disordered over two sites, with refined occupancies of 0.654 (8) and 0.346 (8). Intramolecular C—H···N hydrogen bonds determine the conformation of the molecule. As can be seen from the packing diagram (Fig. 2), intermolecular C—H···N hydrogen bonds (Table 1) link the molecules. There are no π-π interactions.

Related literature top

Related biological activity is described by Kondo et al. (1986) and pharmaceutical activity is described by Bayomi et al. (1986). For related literature, see: Ding et al. (2004); Hu et al. (2005); Xu et al. (2005); Zheng et al. (2006).

Experimental top

To a solution of ethyl 3-triphenylphosphoranylideneamino- 4-cyano-1-phenyl-1H-pyrrole-2-carboxylate(1.55 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added p-chlorophenyl isocyanate (0.46 g, 3 mmol) under dry nitrogen at room temperature. The reaction mixture was left unstirred for 3 h at room temperature and then the solvent was removed under reduced pressure; diethyl ether-petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solution of the carbodiimide (3 mmol) was added to a solution of diisobutylamine (3 mmol) in anhydrous dichloromethane (15 ml). After stirring the reaction mixture for 6 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, in a yield of 94%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Only the major disorder component is shown.
	Fig. 2. The packing in the crystal structure, showing the C—H···N hydrogen bonds as dashed lines. Only the major disorder component is shown.

3-(4-Chlorophenyl)-2-(diisobutylamino)-4-oxo-5-phenyl-4,5-dihydro- 3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile top

Crystal data top

C₂₇H₂₈ClN₅O	Z = 2
M_r = 473.99	F(000) = 500
Triclinic, P1	D_x = 1.244 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7272 (6) Å	Cell parameters from 2745 reflections
b = 12.7635 (9) Å	θ = 2.7–23.6°
c = 13.3411 (9) Å	µ = 0.18 mm⁻¹
α = 103.821 (1)°	T = 298 K
β = 107.828 (1)°	Block, colourless
γ = 106.684 (1)°	0.20 × 0.20 × 0.10 mm
V = 1265.14 (15) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3633 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
φ and ω scans	h = −9→10
9851 measured reflections	k = −15→15
4890 independent reflections	l = −15→16

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0719P)² + 0.5686P] where P = (F_o² + 2F_c²)/3
4890 reflections	(Δ/σ)_max = 0.001
341 parameters	Δρ_max = 0.34 e Å⁻³
7 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₇H₂₈ClN₅O	γ = 106.684 (1)°
M_r = 473.99	V = 1265.14 (15) Å³
Triclinic, P1	Z = 2
a = 8.7272 (6) Å	Mo Kα radiation
b = 12.7635 (9) Å	µ = 0.18 mm⁻¹
c = 13.3411 (9) Å	T = 298 K
α = 103.821 (1)°	0.20 × 0.20 × 0.10 mm
β = 107.828 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3633 reflections with I > 2σ(I)
9851 measured reflections	R_int = 0.031
4890 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	7 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
4890 reflections	Δρ_min = −0.31 e Å⁻³
341 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	Occ. (<1)
C1	0.6572 (4)	0.2077 (2)	−0.3739 (2)	0.0583 (7)
C2	0.8171 (4)	0.1998 (3)	−0.3345 (3)	0.0717 (8)
H2	0.8463	0.1702	−0.2773	0.086*
C3	0.9347 (5)	0.2372 (3)	−0.3822 (4)	0.0979 (13)
H3	1.0439	0.2332	−0.3560	0.117*
C4	0.8914 (7)	0.2792 (4)	−0.4661 (4)	0.1122 (16)
H4	0.9708	0.3037	−0.4972	0.135*
C5	0.7319 (8)	0.2857 (4)	−0.5054 (3)	0.1098 (15)
H5	0.7033	0.3143	−0.5635	0.132*
C6	0.6124 (5)	0.2502 (3)	−0.4597 (2)	0.0789 (9)
H6	0.5038	0.2550	−0.4864	0.095*
C7	0.3635 (3)	0.0923 (2)	−0.3943 (2)	0.0576 (7)
H7	0.3168	0.0582	−0.4725	0.069*
C8	0.2730 (3)	0.0730 (2)	−0.3284 (2)	0.0524 (6)
C9	0.3922 (3)	0.1419 (2)	−0.2150 (2)	0.0465 (6)
C10	0.5506 (3)	0.1993 (2)	−0.2167 (2)	0.0458 (6)
C11	0.0965 (4)	−0.0033 (3)	−0.3641 (2)	0.0588 (7)
C12	0.6998 (3)	0.2731 (2)	−0.1157 (2)	0.0474 (6)
C13	0.4921 (3)	0.2192 (2)	−0.0253 (2)	0.0452 (6)
C14	0.8127 (3)	0.3093 (2)	0.08604 (19)	0.0452 (6)
C15	0.8359 (3)	0.2254 (2)	0.1313 (2)	0.0539 (6)
H15	0.7576	0.1477	0.0944	0.065*
C16	0.9774 (4)	0.2580 (3)	0.2325 (2)	0.0619 (7)
H16	0.9936	0.2029	0.2647	0.074*
C17	1.0926 (3)	0.3731 (3)	0.2840 (2)	0.0610 (7)
C18	1.0724 (3)	0.4560 (3)	0.2376 (2)	0.0581 (7)
H18	1.1532	0.5332	0.2733	0.070*
C19	0.9316 (3)	0.4243 (2)	0.1376 (2)	0.0494 (6)
H19	0.9169	0.4796	0.1052	0.059*
C20	0.5447 (3)	0.3511 (2)	0.1614 (2)	0.0586 (7)
H20A	0.6423	0.3999	0.1510	0.070*	0.654 (8)
H20B	0.5915	0.3435	0.2340	0.070*	0.654 (8)
H20C	0.5014	0.3445	0.2194	0.070*	0.346 (8)
H20D	0.6700	0.3725	0.1957	0.070*	0.346 (8)
C21	0.4228 (6)	0.4153 (4)	0.1662 (4)	0.0573 (15)	0.654 (8)
H21A	0.3360	0.3718	0.1893	0.069*	0.654 (8)
C22	0.5259 (10)	0.5372 (6)	0.2575 (6)	0.084 (2)	0.654 (8)
H22A	0.6041	0.5850	0.2338	0.125*	0.654 (8)
H22B	0.5921	0.5309	0.3263	0.125*	0.654 (8)
H22C	0.4465	0.5724	0.2696	0.125*	0.654 (8)
C23	0.3231 (13)	0.4174 (11)	0.0508 (7)	0.107 (5)	0.654 (8)
H23A	0.2257	0.4376	0.0522	0.161*	0.654 (8)
H23B	0.2815	0.3415	−0.0058	0.161*	0.654 (8)
H23C	0.3996	0.4745	0.0338	0.161*	0.654 (8)
C21'	0.5166 (11)	0.4456 (6)	0.1302 (7)	0.066 (3)	0.346 (8)
H21B	0.5812	0.4620	0.0834	0.080*	0.346 (8)
C22'	0.601 (2)	0.5543 (10)	0.2397 (11)	0.108 (5)	0.346 (8)
H22D	0.5362	0.5428	0.2856	0.161*	0.346 (8)
H22E	0.5994	0.6223	0.2211	0.161*	0.346 (8)
H22F	0.7195	0.5654	0.2804	0.161*	0.346 (8)
C23'	0.3252 (13)	0.4234 (14)	0.0624 (12)	0.063 (6)	0.346 (8)
H23D	0.2529	0.3879	0.0966	0.094*	0.346 (8)
H23E	0.2873	0.3721	−0.0137	0.094*	0.346 (8)
H23F	0.3159	0.4965	0.0621	0.094*	0.346 (8)
C24	0.3096 (3)	0.1501 (2)	0.0690 (2)	0.0563 (7)
H24A	0.2697	0.0782	0.0058	0.068*
H24B	0.2192	0.1813	0.0549	0.068*
C25	0.3327 (5)	0.1218 (3)	0.1749 (3)	0.0758 (9)
H25	0.3541	0.1921	0.2356	0.091*
C26	0.4823 (5)	0.0853 (4)	0.2111 (3)	0.0942 (11)
H26A	0.4693	0.0211	0.1499	0.141*
H26B	0.4842	0.0614	0.2743	0.141*
H26C	0.5898	0.1500	0.2325	0.141*
C27	0.1616 (5)	0.0258 (4)	0.1541 (4)	0.1064 (14)
H27A	0.1414	−0.0451	0.0974	0.160*
H27B	0.0667	0.0501	0.1290	0.160*
H27C	0.1693	0.0121	0.2228	0.160*
Cl1	1.27079 (11)	0.41284 (9)	0.41014 (7)	0.0982 (4)
N1	0.5307 (3)	0.16805 (19)	−0.32917 (17)	0.0524 (5)
N2	−0.0439 (3)	−0.0646 (3)	−0.3894 (2)	0.0774 (8)
N3	0.3580 (2)	0.15372 (19)	−0.12032 (17)	0.0497 (5)
N4	0.6615 (2)	0.27220 (18)	−0.01855 (16)	0.0462 (5)
N5	0.4693 (3)	0.23473 (18)	0.07389 (16)	0.0501 (5)
O1	0.8471 (2)	0.32784 (18)	−0.10456 (16)	0.0667 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0707 (18)	0.0551 (16)	0.0468 (15)	0.0199 (14)	0.0289 (14)	0.0130 (12)
C2	0.0692 (19)	0.0645 (19)	0.086 (2)	0.0272 (16)	0.0413 (17)	0.0191 (16)
C3	0.092 (3)	0.086 (3)	0.123 (3)	0.031 (2)	0.069 (3)	0.020 (2)
C4	0.133 (4)	0.099 (3)	0.099 (3)	0.016 (3)	0.082 (3)	0.018 (3)
C5	0.158 (4)	0.101 (3)	0.061 (2)	0.022 (3)	0.058 (3)	0.028 (2)
C6	0.098 (2)	0.083 (2)	0.0471 (17)	0.0248 (19)	0.0292 (17)	0.0220 (16)
C7	0.0574 (16)	0.0665 (17)	0.0382 (14)	0.0220 (14)	0.0110 (12)	0.0144 (12)
C8	0.0476 (14)	0.0623 (16)	0.0398 (13)	0.0215 (12)	0.0098 (11)	0.0158 (12)
C9	0.0461 (13)	0.0525 (14)	0.0407 (13)	0.0230 (11)	0.0141 (11)	0.0159 (11)
C10	0.0476 (13)	0.0510 (14)	0.0389 (13)	0.0222 (11)	0.0155 (11)	0.0151 (11)
C11	0.0538 (17)	0.0764 (19)	0.0409 (14)	0.0235 (15)	0.0128 (12)	0.0228 (13)
C12	0.0469 (14)	0.0478 (14)	0.0451 (14)	0.0181 (11)	0.0163 (11)	0.0158 (11)
C13	0.0444 (13)	0.0487 (14)	0.0435 (13)	0.0233 (11)	0.0154 (11)	0.0149 (11)
C14	0.0419 (13)	0.0529 (14)	0.0389 (12)	0.0222 (11)	0.0125 (10)	0.0135 (11)
C15	0.0500 (14)	0.0516 (15)	0.0530 (15)	0.0213 (12)	0.0140 (12)	0.0141 (12)
C16	0.0609 (17)	0.0708 (19)	0.0602 (17)	0.0329 (15)	0.0182 (14)	0.0330 (15)
C17	0.0485 (15)	0.082 (2)	0.0450 (15)	0.0242 (14)	0.0092 (12)	0.0242 (14)
C18	0.0480 (14)	0.0600 (16)	0.0472 (15)	0.0110 (12)	0.0087 (12)	0.0134 (13)
C19	0.0477 (14)	0.0484 (14)	0.0483 (14)	0.0188 (11)	0.0149 (11)	0.0167 (12)
C20	0.0548 (15)	0.0676 (18)	0.0500 (15)	0.0289 (14)	0.0208 (13)	0.0100 (13)
C21	0.063 (3)	0.063 (3)	0.065 (3)	0.034 (2)	0.037 (2)	0.030 (2)
C22	0.097 (5)	0.066 (4)	0.103 (5)	0.041 (3)	0.057 (4)	0.023 (3)
C23	0.127 (10)	0.163 (11)	0.114 (9)	0.116 (8)	0.067 (7)	0.090 (8)
C21'	0.078 (6)	0.069 (6)	0.088 (7)	0.041 (5)	0.056 (5)	0.041 (5)
C22'	0.125 (12)	0.059 (7)	0.162 (14)	0.046 (8)	0.082 (11)	0.035 (8)
C23'	0.061 (10)	0.062 (9)	0.070 (10)	0.015 (7)	0.036 (8)	0.030 (7)
C24	0.0582 (16)	0.0648 (17)	0.0486 (15)	0.0251 (13)	0.0239 (13)	0.0207 (13)
C25	0.093 (2)	0.084 (2)	0.068 (2)	0.0432 (19)	0.0426 (18)	0.0344 (18)
C26	0.118 (3)	0.099 (3)	0.090 (3)	0.060 (2)	0.042 (2)	0.053 (2)
C27	0.111 (3)	0.135 (4)	0.117 (3)	0.050 (3)	0.072 (3)	0.082 (3)
Cl1	0.0706 (5)	0.1232 (8)	0.0647 (5)	0.0239 (5)	−0.0087 (4)	0.0374 (5)
N1	0.0533 (12)	0.0604 (13)	0.0385 (11)	0.0190 (11)	0.0168 (10)	0.0155 (10)
N2	0.0567 (16)	0.098 (2)	0.0611 (16)	0.0145 (14)	0.0131 (12)	0.0334 (15)
N3	0.0417 (11)	0.0598 (13)	0.0412 (11)	0.0191 (10)	0.0120 (9)	0.0140 (10)
N4	0.0411 (11)	0.0522 (12)	0.0381 (11)	0.0170 (9)	0.0106 (9)	0.0126 (9)
N5	0.0482 (12)	0.0577 (13)	0.0399 (11)	0.0214 (10)	0.0159 (9)	0.0118 (10)
O1	0.0501 (11)	0.0781 (13)	0.0556 (11)	0.0079 (10)	0.0209 (9)	0.0185 (10)

Geometric parameters (Å, º) top

C1—C2	1.375 (4)	C20—C21'	1.427 (7)
C1—C6	1.379 (4)	C20—N5	1.464 (3)
C1—N1	1.434 (3)	C20—C21	1.524 (4)
C2—C3	1.397 (5)	C20—H20A	0.9700
C2—H2	0.9300	C20—H20B	0.9700
C3—C4	1.351 (6)	C20—H20C	0.9700
C3—H3	0.9300	C20—H20D	0.9700
C4—C5	1.364 (6)	C21—C22	1.528 (6)
C4—H4	0.9300	C21—C23	1.529 (7)
C5—C6	1.384 (5)	C21—H21A	0.9800
C5—H5	0.9300	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—N1	1.353 (3)	C22—H22C	0.9600
C7—C8	1.369 (4)	C23—H23A	0.9600
C7—H7	0.9300	C23—H23B	0.9600
C8—C11	1.420 (4)	C23—H23C	0.9600
C8—C9	1.421 (3)	C21'—C23'	1.539 (9)
C9—N3	1.368 (3)	C21'—C22'	1.545 (9)
C9—C10	1.376 (3)	C21'—H21B	0.9800
C10—N1	1.398 (3)	C22'—H22D	0.9600
C10—C12	1.419 (3)	C22'—H22E	0.9600
C11—N2	1.139 (3)	C22'—H22F	0.9600
C12—O1	1.217 (3)	C23'—H23D	0.9600
C12—N4	1.435 (3)	C23'—H23E	0.9600
C13—N3	1.303 (3)	C23'—H23F	0.9600
C13—N5	1.373 (3)	C24—N5	1.470 (3)
C13—N4	1.403 (3)	C24—C25	1.509 (4)
C14—C19	1.382 (3)	C24—H24A	0.9700
C14—C15	1.383 (4)	C24—H24B	0.9700
C14—N4	1.452 (3)	C25—C26	1.492 (5)
C15—C16	1.391 (4)	C25—C27	1.531 (5)
C15—H15	0.9300	C25—H25	0.9800
C16—C17	1.374 (4)	C26—H26A	0.9600
C16—H16	0.9300	C26—H26B	0.9600
C17—C18	1.374 (4)	C26—H26C	0.9600
C17—Cl1	1.745 (3)	C27—H27A	0.9600
C18—C19	1.381 (3)	C27—H27B	0.9600
C18—H18	0.9300	C27—H27C	0.9600
C19—H19	0.9300

C2—C1—C6	120.9 (3)	H20B—C20—H20C	45.8
C2—C1—N1	120.6 (3)	C21'—C20—H20D	107.7
C6—C1—N1	118.4 (3)	N5—C20—H20D	107.2
C1—C2—C3	118.6 (3)	C21—C20—H20D	135.3
C1—C2—H2	120.7	H20A—C20—H20D	46.9
C3—C2—H2	120.7	H20B—C20—H20D	62.9
C4—C3—C2	120.6 (4)	H20C—C20—H20D	106.9
C4—C3—H3	119.7	C20—C21—C22	109.4 (4)
C2—C3—H3	119.7	C20—C21—C23	112.2 (5)
C3—C4—C5	120.4 (4)	C22—C21—C23	113.2 (5)
C3—C4—H4	119.8	C20—C21—H20C	37.8
C5—C4—H4	119.8	C22—C21—H20C	101.6
C4—C5—C6	120.6 (4)	C23—C21—H20C	142.0
C4—C5—H5	119.7	C20—C21—H21A	107.2
C6—C5—H5	119.7	C22—C21—H21A	107.2
C1—C6—C5	118.8 (4)	C23—C21—H21A	107.2
C1—C6—H6	120.6	H20C—C21—H21A	74.9
C5—C6—H6	120.6	C20—C21'—C23'	115.8 (8)
N1—C7—C8	110.2 (2)	C20—C21'—C22'	107.1 (8)
N1—C7—H7	124.9	C23'—C21'—C22'	111.4 (7)
C8—C7—H7	124.9	C20—C21'—H21B	107.4
C7—C8—C11	127.5 (2)	C23'—C21'—H21B	107.4
C7—C8—C9	106.6 (2)	C22'—C21'—H21B	107.4
C11—C8—C9	125.9 (2)	C21'—C22'—H22D	109.5
N3—C9—C10	125.2 (2)	C21'—C22'—H22E	109.5
N3—C9—C8	127.3 (2)	H22D—C22'—H22E	109.5
C10—C9—C8	107.4 (2)	C21'—C22'—H22F	109.5
C9—C10—N1	107.9 (2)	H22D—C22'—H22F	109.5
C9—C10—C12	121.4 (2)	H22E—C22'—H22F	109.5
N1—C10—C12	130.6 (2)	C21'—C23'—H23D	109.5
N2—C11—C8	177.8 (3)	C21'—C23'—H23E	109.5
O1—C12—C10	128.5 (2)	H23D—C23'—H23E	109.5
O1—C12—N4	120.4 (2)	C21'—C23'—H23F	109.5
C10—C12—N4	111.0 (2)	H23D—C23'—H23F	109.5
N3—C13—N5	119.1 (2)	H23E—C23'—H23F	109.5
N3—C13—N4	123.1 (2)	N5—C24—C25	113.9 (2)
N5—C13—N4	117.8 (2)	N5—C24—H24A	108.8
C19—C14—C15	121.0 (2)	C25—C24—H24A	108.8
C19—C14—N4	121.1 (2)	N5—C24—H24B	108.8
C15—C14—N4	117.9 (2)	C25—C24—H24B	108.8
C14—C15—C16	119.6 (3)	H24A—C24—H24B	107.7
C14—C15—H15	120.2	C26—C25—C24	113.1 (3)
C16—C15—H15	120.2	C26—C25—C27	110.8 (3)
C17—C16—C15	118.8 (3)	C24—C25—C27	108.1 (3)
C17—C16—H16	120.6	C26—C25—H25	108.2
C15—C16—H16	120.6	C24—C25—H25	108.2
C18—C17—C16	121.7 (2)	C27—C25—H25	108.2
C18—C17—Cl1	119.8 (2)	C25—C26—H26A	109.5
C16—C17—Cl1	118.5 (2)	C25—C26—H26B	109.5
C17—C18—C19	119.7 (3)	H26A—C26—H26B	109.5
C17—C18—H18	120.2	C25—C26—H26C	109.5
C19—C18—H18	120.2	H26A—C26—H26C	109.5
C18—C19—C14	119.2 (2)	H26B—C26—H26C	109.5
C18—C19—H19	120.4	C25—C27—H27A	109.5
C14—C19—H19	120.4	C25—C27—H27B	109.5
C21'—C20—N5	118.7 (4)	H27A—C27—H27B	109.5
C21'—C20—C21	43.4 (3)	C25—C27—H27C	109.5
N5—C20—C21	116.8 (3)	H27A—C27—H27C	109.5
C21'—C20—H20A	66.6	H27B—C27—H27C	109.5
N5—C20—H20A	108.1	C7—N1—C10	107.9 (2)
C21—C20—H20A	108.1	C7—N1—C1	123.4 (2)
C21'—C20—H20B	132.5	C10—N1—C1	128.7 (2)
N5—C20—H20B	108.1	C13—N3—C9	115.4 (2)
C21—C20—H20B	108.1	C13—N4—C12	123.18 (19)
H20A—C20—H20B	107.3	C13—N4—C14	120.53 (19)
C21'—C20—H20C	108.0	C12—N4—C14	115.23 (18)
N5—C20—H20C	107.8	C13—N5—C20	121.0 (2)
C21—C20—H20C	68.0	C13—N5—C24	116.4 (2)
H20A—C20—H20C	140.9	C20—N5—C24	116.6 (2)

C6—C1—C2—C3	0.8 (5)	N5—C20—C21'—C22'	176.7 (7)
N1—C1—C2—C3	178.6 (3)	C21—C20—C21'—C22'	77.0 (8)
C1—C2—C3—C4	−0.7 (5)	N5—C24—C25—C26	−52.2 (4)
C2—C3—C4—C5	0.1 (6)	N5—C24—C25—C27	−175.3 (3)
C3—C4—C5—C6	0.4 (7)	C8—C7—N1—C10	0.1 (3)
C2—C1—C6—C5	−0.4 (5)	C8—C7—N1—C1	−178.5 (2)
N1—C1—C6—C5	−178.3 (3)	C9—C10—N1—C7	−0.5 (3)
C4—C5—C6—C1	−0.2 (6)	C12—C10—N1—C7	178.1 (3)
N1—C7—C8—C11	−177.9 (3)	C9—C10—N1—C1	178.0 (2)
N1—C7—C8—C9	0.3 (3)	C12—C10—N1—C1	−3.4 (4)
C7—C8—C9—N3	177.4 (2)	C2—C1—N1—C7	−127.9 (3)
C11—C8—C9—N3	−4.3 (4)	C6—C1—N1—C7	49.9 (4)
C7—C8—C9—C10	−0.6 (3)	C2—C1—N1—C10	53.7 (4)
C11—C8—C9—C10	177.6 (3)	C6—C1—N1—C10	−128.4 (3)
N3—C9—C10—N1	−177.4 (2)	N5—C13—N3—C9	−179.4 (2)
C8—C9—C10—N1	0.7 (3)	N4—C13—N3—C9	−1.6 (3)
N3—C9—C10—C12	3.8 (4)	C10—C9—N3—C13	−4.7 (4)
C8—C9—C10—C12	−178.1 (2)	C8—C9—N3—C13	177.6 (2)
C7—C8—C11—N2	156 (9)	N3—C13—N4—C12	8.9 (4)
C9—C8—C11—N2	−22 (9)	N5—C13—N4—C12	−173.2 (2)
C9—C10—C12—O1	179.2 (3)	N3—C13—N4—C14	−158.8 (2)
N1—C10—C12—O1	0.8 (5)	N5—C13—N4—C14	19.1 (3)
C9—C10—C12—N4	3.0 (3)	O1—C12—N4—C13	174.5 (2)
N1—C10—C12—N4	−175.5 (2)	C10—C12—N4—C13	−9.0 (3)
C19—C14—C15—C16	2.5 (4)	O1—C12—N4—C14	−17.3 (3)
N4—C14—C15—C16	−178.8 (2)	C10—C12—N4—C14	159.3 (2)
C14—C15—C16—C17	−1.2 (4)	C19—C14—N4—C13	−122.7 (3)
C15—C16—C17—C18	−0.7 (4)	C15—C14—N4—C13	58.6 (3)
C15—C16—C17—Cl1	−179.3 (2)	C19—C14—N4—C12	68.6 (3)
C16—C17—C18—C19	1.1 (4)	C15—C14—N4—C12	−110.0 (3)
Cl1—C17—C18—C19	179.8 (2)	N3—C13—N5—C20	−134.4 (2)
C17—C18—C19—C14	0.2 (4)	N4—C13—N5—C20	47.6 (3)
C15—C14—C19—C18	−2.1 (4)	N3—C13—N5—C24	17.5 (3)
N4—C14—C19—C18	179.3 (2)	N4—C13—N5—C24	−160.5 (2)
C21'—C20—C21—C22	−72.3 (6)	C21'—C20—N5—C13	49.7 (5)
N5—C20—C21—C22	−176.7 (4)	C21—C20—N5—C13	99.0 (3)
C21'—C20—C21—C23	54.2 (8)	C21'—C20—N5—C24	−102.2 (5)
N5—C20—C21—C23	−50.2 (6)	C21—C20—N5—C24	−52.8 (4)
N5—C20—C21'—C23'	51.8 (10)	C25—C24—N5—C13	145.7 (2)
C21—C20—C21'—C23'	−47.9 (8)	C25—C24—N5—C20	−61.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···N3	0.97	2.35	2.694 (3)	100
C23—H23B···N5	0.96	2.57	2.995 (11)	107
C20—H20A···N4	0.97	2.54	2.958 (3)	106
C7—H7···N2ⁱ	0.93	2.56	3.202 (4)	126

Symmetry code: (i) −x, −y, −z−1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₈ClN₅O
M_r	473.99
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7272 (6), 12.7635 (9), 13.3411 (9)
α, β, γ (°)	103.821 (1), 107.828 (1), 106.684 (1)
V (Å³)	1265.14 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9851, 4890, 3633
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.170, 1.01
No. of reflections	4890
No. of parameters	341
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).