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The crystal structure of 11-[4-(1,3-benzodioxol-5-yl­methyl)­piperazino]-8-chloro-5H-dibenzo­[b,e][1,4]­diazepine, C25H23ClN4O2, confirms the buckled nature of the dibenzodiazepine nucleus, with the central seven-membered heterocycle in a boat conformation and the dihedral angle between the planes of the aromatic rings being similar to that found for the parent compound, clozapine. The piperazine ring displays an almost perfect chair conformation, with the piperonyl group assuming an equatorial orientation. The relative position of the dibenzodiazepine and piperazine ring systems is controlled by the planarity of the piperazine N atom in the amidine moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199015139/ta1272sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199015139/ta1272Isup2.hkl
Contains datablock I

CCDC reference: 143248

Comment top

Schizophrenia is a debilitating mental disorder characterized by the chaotic jumbling and breakdown of internal thought processes. The symptoms of this disease can be divided into two distinct categories, positive (delusions and hallucinations) and negative (social and emotional withdrawal). Therapeutics used to treat this disorder fall into two clinical classes, typical and atypical. Typical antipsychotics exhibit efficacy against the positive symptoms of schizophrenia but, as an undesirable side effect, have a propensity to induce movement disorders such as Parkinsonism. Atypical antipsychotics, on the other hand, are efficacious against both the positive and negative symptoms of schizophrenia, and are virtually devoid of such side effects.

Clozapine is an atypical antipsychotic unparalleled in its efficacy against treatment-resistant schizophrenia. The therapeutic action of clozapine against delusions and hallucinations is thought to be due, in part, to its affinity and selectivity for dopamine-D4 receptors (Van-Tol et al., 1991; Seeman, 1992). These findings have sparked considerable interest in the area of selective D4 ligands (Boyfield et al., 1996; Mansbach et al., 1998) and our research attention has been directed towards the synthesis of a family of clozapine analogues. The title compound, (I), has been patented as a selective dopamine-D4 antagonist (Tehim et al., 1998) for potential use in the treatment of anxiety and schizophrenia, while the related dibenzoxazepine, formed by solitary isosteric replacement of NH by O, displays approximately twenty-fold greater selectivity for the D4 receptor compared to the D2 receptor, this latter dopamine receptor subtype having been implicated in drug-induced movement disorders (Kufferle et al., 1997). Our interest in the crystal structure of (I) was to examine the effect of the arylmethyl substituent on the geometries of the piperazine ring and the tricyclic nucleus, relative to clozapine. \scheme

The conformation of the clozapine moiety in (I) is similar to that observed in the parent compound, clozapine (Petcher & Weber, 1976), showing the buckled nature of the dibenzodiazepine nucleus with the central seven-membered heterocycle in a boat conformation. The dihedral angle between the planes of the benzene rings (defined as the obtuse angle subtended by the plane normals) is 120.73 (6)°, similar to the 115° observed in clozapine, while the dihedral angles between the plane of the four C atoms in the piperizine ring and the chloro-substituted and unsubstituted aromatic rings are 29.67 (10) and 33.85 (10)°, respectively (for clozapine the angles are 40.5 and 31.8°, respectively), a consequence of the planarity of the piperazine N in the amidine moiety and the partial double bond character of N1'-C11. As in clozapine, the piperazine ring in (I) adopts an almost perfect chair conformation, with the piperonyl group assuming an equatorial orientation. The nine atoms of this group are coplanar, with the orientation such that the dihedral angle between this plane and the plane of the C atoms in the piperazine ring is 80.21 (6)°, while the torsion angles C5'-N4'-C1''-C5''' and N4'-C1''-C5'''-C4''' are -167.71 (14) and 42.8 (2)°, respectively.

There is a very weak hydrogen-bonded interaction between the H atom on N5 and N10 of an adjacent molecule [N5···N10i 3.291 (2), N5—H(N5) 0.88 (2) and H(N5)···N10i 2.46 (2) Å, and N5—H(N5)···N10i 159 (2)°; symmetry code (i): x, 1/2 - y, -1/2 + z]. This is achieved, despite the sterically congested area around N10, by the dibenzodiazepine rings of the two molecules being almost perpendicular, the dihedral angle between the C4a—N5—C5a and C9ai—N10i—C11i planes being 89.32 (17)°. No such interaction was found for clozapine.

Experimental top

Compound (I) was synthesized using a modification of the literature procedure for the synthesis of clozapine (Schneider, 1976). The method entailed reaction of 8-chloro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one and the titanium tetrakisamine complex of N-piperonylpiperazine in anisole. The crude product was purified by flash chromatography (Still et al., 1978) and the product recrystallized from dichloromethane-hexane as bright yellow prisms (m.p. 429–430 K; yield: 50%).

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PROCESS_DATA (Gable et al., 1993); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL93.

Figures top
[Figure 1] Fig. 1. An ORTEPII (Johnson, 1976) drawing of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of radius 0.1 Å.
11-[4-(1,3-benzodioxol-5-ylmethyl)piperazino]-8-chloro-5H- dibenzo[b,e][1,4]diazepine top
Crystal data top
C25H23ClN4O2F(000) = 936
Mr = 446.92Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.097 (2) ÅCell parameters from 25 reflections
b = 16.169 (2) Åθ = 11.3–16.3°
c = 10.752 (2) ŵ = 0.20 mm1
β = 95.818 (12)°T = 293 K
V = 2265.2 (6) Å3Prism, intense yellow
Z = 40.60 × 0.57 × 0.53 mm
Data collection top
Enraf-Nonius CAD-4 MACHS
diffractometer
3884 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω/2θ scansh = 1616
Absorption correction: gaussian
(SHELX76; Sheldrick, 1976)
k = 120
Tmin = 0.893, Tmax = 0.918l = 113
6392 measured reflections3 standard reflections every 150 min
5171 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039All H-atom parameters refined
wR(F2) = 0.097Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 0.5782P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5169 reflectionsΔρmax = 0.18 e Å3
382 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL93 (Sheldrick, 1993), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0085 (8)
Crystal data top
C25H23ClN4O2V = 2265.2 (6) Å3
Mr = 446.92Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.097 (2) ŵ = 0.20 mm1
b = 16.169 (2) ÅT = 293 K
c = 10.752 (2) Å0.60 × 0.57 × 0.53 mm
β = 95.818 (12)°
Data collection top
Enraf-Nonius CAD-4 MACHS
diffractometer
3884 reflections with I > 2σ(I)
Absorption correction: gaussian
(SHELX76; Sheldrick, 1976)
Rint = 0.012
Tmin = 0.893, Tmax = 0.9183 standard reflections every 150 min
6392 measured reflections intensity decay: none
5171 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.097All H-atom parameters refined
S = 1.03Δρmax = 0.18 e Å3
5169 reflectionsΔρmin = 0.25 e Å3
382 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 on F2 for ALL reflections except for 2 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
Cl0.45018 (3)0.14459 (4)0.13562 (5)0.0762 (2)
O1'''0.39203 (13)0.07310 (14)0.72440 (13)0.0965 (5)
O3'''0.39816 (15)0.18221 (11)0.5854 (2)0.1012 (6)
N50.07419 (11)0.23454 (9)0.18901 (13)0.0518 (3)
N100.06352 (9)0.15583 (8)0.05209 (11)0.0429 (3)
N1'0.10614 (9)0.12330 (9)0.04731 (11)0.0510 (3)
N4'0.27418 (9)0.06931 (8)0.17479 (11)0.0470 (3)
C10.08449 (13)0.04493 (11)0.1933 (2)0.0539 (4)
C20.0975 (2)0.02737 (14)0.3196 (2)0.0670 (5)
C30.0576 (2)0.07995 (14)0.4026 (2)0.0728 (6)
C40.0016 (2)0.14813 (13)0.3610 (2)0.0633 (5)
C4a0.01332 (12)0.16618 (10)0.23385 (14)0.0466 (3)
C5a0.16440 (12)0.21268 (9)0.11232 (13)0.0439 (3)
C60.26076 (14)0.23485 (11)0.1435 (2)0.0551 (4)
C70.34935 (13)0.21644 (11)0.0681 (2)0.0560 (4)
C80.34058 (12)0.17165 (10)0.03906 (14)0.0479 (3)
C90.24608 (11)0.14841 (9)0.07271 (13)0.0423 (3)
C9a0.15591 (11)0.16973 (8)0.00013 (12)0.0393 (3)
C110.02098 (11)0.13545 (9)0.01344 (13)0.0424 (3)
C11a0.03146 (11)0.11566 (9)0.14942 (13)0.0439 (3)
C2'0.09959 (13)0.12535 (14)0.18384 (15)0.0560 (4)
C3'0.16808 (12)0.05869 (13)0.2277 (2)0.0534 (4)
C5'0.27959 (12)0.06728 (12)0.03858 (15)0.0531 (4)
C6'0.21209 (12)0.13389 (12)0.0081 (2)0.0535 (4)
C1''0.33875 (13)0.00562 (12)0.2236 (2)0.0545 (4)
C2'''0.4149 (3)0.1568 (3)0.7089 (3)0.1125 (11)
C3a'''0.38128 (14)0.10969 (13)0.5242 (2)0.0636 (5)
C4'''0.36823 (13)0.09961 (12)0.4006 (2)0.0580 (4)
C5'''0.35090 (11)0.01943 (11)0.3598 (2)0.0503 (4)
C6'''0.34692 (14)0.04533 (12)0.4440 (2)0.0612 (4)
C7'''0.3616 (2)0.0336 (2)0.5695 (2)0.0717 (5)
C7a'''0.37805 (14)0.04443 (15)0.6065 (2)0.0667 (5)
HN50.0882 (14)0.2679 (12)0.2493 (18)0.063 (5)*
H10.1103 (14)0.0070 (12)0.1354 (17)0.064 (5)*
H20.1332 (15)0.0210 (12)0.3484 (18)0.069 (6)*
H30.0660 (17)0.0693 (14)0.491 (2)0.090 (7)*
H40.0282 (14)0.1844 (12)0.4160 (18)0.067 (6)*
H60.2660 (15)0.2638 (12)0.2193 (18)0.072 (6)*
H70.4165 (15)0.2344 (11)0.0892 (17)0.065 (5)*
H90.2420 (12)0.1175 (10)0.1489 (16)0.050 (4)*
H2'A0.0282 (15)0.1165 (11)0.2179 (16)0.062 (5)*
H2'B0.1221 (14)0.1808 (12)0.2071 (17)0.063 (5)*
H3'A0.1679 (13)0.0628 (10)0.3179 (16)0.056 (5)*
H3'B0.1411 (15)0.0033 (13)0.2042 (18)0.072 (6)*
H5'A0.2584 (14)0.0105 (12)0.0032 (17)0.068 (5)*
H5'B0.3503 (14)0.0758 (11)0.0048 (16)0.058 (5)*
H6'A0.2135 (13)0.1330 (10)0.0971 (17)0.054 (5)*
H6'B0.2358 (14)0.1893 (12)0.0144 (16)0.061 (5)*
H1''A0.4061 (14)0.0088 (11)0.1737 (16)0.061 (5)*
H1''B0.3103 (15)0.0515 (13)0.2103 (17)0.071 (6)*
H2'''A0.490 (3)0.171 (2)0.718 (3)0.169 (14)*
H2'''B0.370 (3)0.192 (2)0.764 (3)0.156 (14)*
H4'''0.3684 (15)0.1457 (12)0.3427 (19)0.071 (6)*
H6'''0.3349 (16)0.0993 (14)0.4147 (19)0.080 (6)*
H7'''0.3587 (18)0.0776 (15)0.626 (2)0.091 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0466 (2)0.0962 (4)0.0833 (4)0.0014 (2)0.0059 (2)0.0199 (3)
O1'''0.0995 (12)0.138 (2)0.0532 (8)0.0068 (11)0.0139 (8)0.0020 (9)
O3'''0.1308 (15)0.0981 (12)0.0781 (10)0.0272 (10)0.0276 (10)0.0176 (9)
N50.0612 (8)0.0492 (8)0.0440 (7)0.0001 (6)0.0008 (6)0.0125 (6)
N100.0441 (6)0.0494 (7)0.0357 (6)0.0026 (5)0.0061 (5)0.0016 (5)
N1'0.0413 (6)0.0746 (9)0.0372 (6)0.0040 (6)0.0040 (5)0.0011 (6)
N4'0.0384 (6)0.0600 (8)0.0430 (7)0.0021 (6)0.0053 (5)0.0023 (6)
C10.0488 (8)0.0605 (10)0.0522 (9)0.0026 (7)0.0035 (7)0.0065 (8)
C20.0637 (11)0.0726 (12)0.0619 (11)0.0050 (9)0.0070 (9)0.0212 (10)
C30.0882 (14)0.0897 (15)0.0376 (9)0.0048 (12)0.0071 (9)0.0107 (10)
C40.0798 (12)0.0718 (12)0.0374 (8)0.0036 (10)0.0009 (8)0.0067 (8)
C4a0.0515 (8)0.0487 (8)0.0386 (7)0.0076 (7)0.0003 (6)0.0031 (6)
C5a0.0525 (8)0.0405 (7)0.0388 (7)0.0006 (6)0.0049 (6)0.0016 (6)
C60.0632 (10)0.0564 (10)0.0471 (9)0.0054 (8)0.0131 (7)0.0108 (8)
C70.0498 (9)0.0615 (10)0.0586 (10)0.0061 (8)0.0151 (7)0.0042 (8)
C80.0450 (8)0.0507 (8)0.0477 (8)0.0001 (7)0.0031 (6)0.0014 (7)
C90.0490 (8)0.0427 (8)0.0351 (7)0.0031 (6)0.0042 (6)0.0013 (6)
C9a0.0462 (7)0.0383 (7)0.0340 (7)0.0020 (6)0.0068 (5)0.0037 (5)
C110.0451 (7)0.0444 (8)0.0380 (7)0.0017 (6)0.0056 (6)0.0014 (6)
C11a0.0417 (7)0.0501 (8)0.0394 (7)0.0040 (6)0.0015 (6)0.0021 (6)
C2'0.0473 (9)0.0822 (13)0.0387 (8)0.0118 (9)0.0051 (7)0.0037 (8)
C3'0.0416 (8)0.0774 (12)0.0410 (8)0.0041 (8)0.0029 (6)0.0036 (8)
C5'0.0384 (8)0.0755 (12)0.0445 (8)0.0000 (8)0.0004 (6)0.0053 (8)
C6'0.0447 (8)0.0725 (12)0.0432 (9)0.0089 (8)0.0037 (6)0.0032 (8)
C1''0.0462 (8)0.0605 (11)0.0573 (10)0.0072 (8)0.0077 (7)0.0037 (8)
C2'''0.122 (3)0.152 (3)0.063 (2)0.032 (2)0.006 (2)0.025 (2)
C3a'''0.0554 (10)0.0748 (12)0.0614 (11)0.0084 (9)0.0100 (8)0.0061 (9)
C4'''0.0557 (9)0.0623 (11)0.0573 (10)0.0060 (8)0.0122 (8)0.0064 (9)
C5'''0.0363 (7)0.0590 (10)0.0562 (9)0.0045 (7)0.0079 (6)0.0023 (7)
C6'''0.0568 (10)0.0581 (11)0.0689 (12)0.0055 (8)0.0066 (8)0.0072 (9)
C7'''0.0668 (12)0.0835 (15)0.0644 (12)0.0061 (10)0.0051 (9)0.0218 (11)
C7a'''0.0510 (9)0.101 (2)0.0489 (10)0.0011 (10)0.0072 (7)0.0059 (10)
Geometric parameters (Å, º) top
Cl—C81.740 (2)C7—C81.376 (2)
O1'''—C7a'''1.379 (2)C7—H70.97 (2)
O1'''—C2'''1.392 (4)C8—C91.377 (2)
O3'''—C3a'''1.373 (2)C9—C9a1.393 (2)
O3'''—C2'''1.428 (3)C9—H90.97 (2)
N5—C5a1.415 (2)C11—C11a1.489 (2)
N5—C4a1.418 (2)C2'—C3'1.508 (2)
N5—HN50.88 (2)C2'—H2'A0.98 (2)
N10—C111.293 (2)C2'—H2'B0.98 (2)
N10—C9a1.403 (2)C3'—H3'A0.97 (2)
N1'—C111.363 (2)C3'—H3'B1.00 (2)
N1'—C2'1.462 (2)C5'—C6'1.511 (2)
N1'—C6'1.464 (2)C5'—H5'A1.04 (2)
N4'—C3'1.457 (2)C5'—H5'B0.97 (2)
N4'—C5'1.459 (2)C6'—H6'A0.96 (2)
N4'—C1''1.463 (2)C6'—H6'B0.99 (2)
C1—C21.381 (2)C1''—C5'''1.506 (2)
C1—C11a1.395 (2)C1''—H1''A0.99 (2)
C1—H10.96 (2)C1''—H1''B1.01 (2)
C2—C31.374 (3)C2'''—H2'''A1.02 (4)
C2—H20.95 (2)C2'''—H2'''B0.97 (4)
C3—C41.374 (3)C3a'''—C4'''1.367 (2)
C3—H30.96 (2)C3a'''—C7a'''1.375 (3)
C4—C4a1.392 (2)C4'''—C5'''1.394 (3)
C4—H40.95 (2)C4'''—H4'''0.97 (2)
C4a—C11a1.394 (2)C5'''—C6'''1.382 (2)
C5a—C61.386 (2)C6'''—C7'''1.395 (3)
C5a—C9a1.406 (2)C6'''—H6'''0.95 (2)
C6—C71.379 (2)C7'''—C7a'''1.346 (3)
C6—H60.95 (2)C7'''—H7'''0.93 (2)
C7a'''—O1'''—C2'''105.3 (2)C3'—C2'—H2'A110.8 (11)
C3a'''—O3'''—C2'''104.3 (2)N1'—C2'—H2'B106.7 (11)
C5a—N5—C4a114.25 (13)C3'—C2'—H2'B111.6 (11)
C5a—N5—HN5111.1 (12)H2'A—C2'—H2'B109.7 (15)
C4a—N5—HN5112.3 (12)N4'—C3'—C2'111.57 (15)
C11—N10—C9a123.24 (12)N4'—C3'—H3'A106.7 (10)
C11—N1'—C2'120.69 (12)C2'—C3'—H3'A108.8 (10)
C11—N1'—C6'125.19 (13)N4'—C3'—H3'B110.6 (11)
C2'—N1'—C6'111.27 (13)C2'—C3'—H3'B108.9 (11)
C3'—N4'—C5'109.66 (12)H3'A—C3'—H3'B110.3 (15)
C3'—N4'—C1''109.87 (13)N4'—C5'—C6'110.29 (14)
C5'—N4'—C1''111.91 (13)N4'—C5'—H5'A113.5 (10)
C2—C1—C11a120.6 (2)C6'—C5'—H5'A108.7 (10)
C2—C1—H1119.4 (11)N4'—C5'—H5'B108.7 (10)
C11a—C1—H1120.0 (11)C6'—C5'—H5'B110.1 (10)
C3—C2—C1119.6 (2)H5'A—C5'—H5'B105.5 (14)
C3—C2—H2120.4 (12)N1'—C6'—C5'110.11 (14)
C1—C2—H2119.9 (12)N1'—C6'—H6'A109.1 (10)
C2—C3—C4120.7 (2)C5'—C6'—H6'A111.7 (10)
C2—C3—H3121.2 (14)N1'—C6'—H6'B108.4 (10)
C4—C3—H3118.0 (14)C5'—C6'—H6'B110.9 (10)
C3—C4—C4a120.4 (2)H6'A—C6'—H6'B106.5 (14)
C3—C4—H4122.3 (12)N4'—C1''—C5'''111.50 (14)
C4a—C4—H4117.3 (12)N4'—C1''—H1''A106.6 (11)
C4—C4a—C11a119.3 (2)C5'''—C1''—H1''A110.2 (10)
C4—C4a—N5121.0 (2)N4'—C1''—H1''B110.9 (11)
C11a—C4a—N5119.62 (13)C5'''—C1''—H1''B110.5 (11)
C6—C5a—C9a119.26 (14)H1''A—C1''—H1''B107.0 (15)
C6—C5a—N5121.42 (14)O1'''—C2'''—O3'''109.8 (2)
C9a—C5a—N5119.29 (13)O1'''—C2'''—H2'''A113 (2)
C7—C6—C5a122.3 (2)O3'''—C2'''—H2'''A106 (2)
C7—C6—H6118.8 (12)O1'''—C2'''—H2'''B113 (2)
C5a—C6—H6118.9 (12)O3'''—C2'''—H2'''B105 (2)
C8—C7—C6118.0 (2)H2'''A—C2'''—H2'''B110 (3)
C8—C7—H7120.4 (11)C4'''—C3a'''—O3'''127.6 (2)
C6—C7—H7121.6 (11)C4'''—C3a'''—C7a'''122.4 (2)
C7—C8—C9121.17 (15)O3'''—C3a'''—C7a'''110.1 (2)
C7—C8—Cl119.88 (12)C3a'''—C4'''—C5'''117.2 (2)
C9—C8—Cl118.94 (12)C3a'''—C4'''—H4'''122.7 (12)
C8—C9—C9a121.22 (14)C5'''—C4'''—H4'''120.1 (12)
C8—C9—H9119.5 (10)C6'''—C5'''—C4'''119.7 (2)
C9a—C9—H9119.2 (10)C6'''—C5'''—C1''121.6 (2)
C9—C9a—N10116.86 (12)C4'''—C5'''—C1''118.7 (2)
C9—C9a—C5a117.94 (13)C5'''—C6'''—C7'''122.0 (2)
N10—C9a—C5a124.68 (13)C5'''—C6'''—H6'''118.5 (13)
N10—C11—N1'118.19 (13)C7'''—C6'''—H6'''119.4 (13)
N10—C11—C11a125.33 (13)C7a'''—C7'''—C6'''117.1 (2)
N1'—C11—C11a116.18 (12)C7a'''—C7'''—H7'''121.4 (14)
C4a—C11a—C1119.19 (15)C6'''—C7'''—H7'''121.5 (14)
C4a—C11a—C11120.69 (13)C7'''—C7a'''—C3a'''121.6 (2)
C1—C11a—C11120.10 (14)C7'''—C7a'''—O1'''128.8 (2)
N1'—C2'—C3'108.75 (14)C3a'''—C7a'''—O1'''109.6 (2)
N1'—C2'—H2'A109.2 (10)
C11a—C1—C2—C30.2 (3)N1'—C11—C11a—C4a139.90 (15)
C1—C2—C3—C42.4 (3)N10—C11—C11a—C1132.0 (2)
C2—C3—C4—C4a1.6 (3)N1'—C11—C11a—C141.6 (2)
C3—C4—C4a—C11a1.8 (3)C11—N1'—C2'—C3'140.7 (2)
C3—C4—C4a—N5177.6 (2)C6'—N1'—C2'—C3'57.4 (2)
C5a—N5—C4a—C4115.3 (2)C5'—N4'—C3'—C2'59.0 (2)
C5a—N5—C4a—C11a64.0 (2)C1''—N4'—C3'—C2'177.63 (14)
C4a—N5—C5a—C6120.9 (2)N1'—C2'—C3'—N4'58.2 (2)
C4a—N5—C5a—C9a61.1 (2)C3'—N4'—C5'—C6'57.9 (2)
C9a—C5a—C6—C70.1 (3)C1''—N4'—C5'—C6'179.94 (14)
N5—C5a—C6—C7177.9 (2)C11—N1'—C6'—C5'141.3 (2)
C5a—C6—C7—C82.6 (3)C2'—N1'—C6'—C5'57.9 (2)
C6—C7—C8—C92.4 (3)N4'—C5'—C6'—N1'57.5 (2)
C6—C7—C8—Cl178.46 (14)C3'—N4'—C1''—C5'''70.2 (2)
C7—C8—C9—C9a0.3 (2)C5'—N4'—C1''—C5'''167.71 (14)
Cl—C8—C9—C9a178.88 (11)C7a'''—O1'''—C2'''—O3'''9.6 (3)
C8—C9—C9a—N10169.38 (13)C3a'''—O3'''—C2'''—O1'''9.2 (3)
C8—C9—C9a—C5a2.8 (2)C2'''—O3'''—C3a'''—C4'''175.2 (2)
C11—N10—C9a—C9147.02 (14)C2'''—O3'''—C3a'''—C7a'''5.3 (3)
C11—N10—C9a—C5a41.4 (2)O3'''—C3a'''—C4'''—C5'''179.3 (2)
C6—C5a—C9a—C92.5 (2)C7a'''—C3a'''—C4'''—C5'''0.2 (3)
N5—C5a—C9a—C9179.41 (13)C3a'''—C4'''—C5'''—C6'''0.4 (2)
C6—C5a—C9a—N10168.96 (14)C3a'''—C4'''—C5'''—C1''178.52 (15)
N5—C5a—C9a—N109.1 (2)N4'—C1''—C5'''—C6'''138.3 (2)
C9a—N10—C11—N1'179.86 (13)N4'—C1''—C5'''—C4'''42.8 (2)
C9a—N10—C11—C11a6.4 (2)C4'''—C5'''—C6'''—C7'''1.2 (3)
C2'—N1'—C11—N105.9 (2)C1''—C5'''—C6'''—C7'''177.7 (2)
C6'—N1'—C11—N10153.3 (2)C5'''—C6'''—C7'''—C7a'''1.3 (3)
C2'—N1'—C11—C11a168.2 (2)C6'''—C7'''—C7a'''—C3a'''0.7 (3)
C6'—N1'—C11—C11a32.6 (2)C6'''—C7'''—C7a'''—O1'''178.2 (2)
C4—C4a—C11a—C14.3 (2)C4'''—C3a'''—C7a'''—C7'''0.1 (3)
N5—C4a—C11a—C1175.04 (14)O3'''—C3a'''—C7a'''—C7'''179.5 (2)
C4—C4a—C11a—C11177.17 (15)C4'''—C3a'''—C7a'''—O1'''179.1 (2)
N5—C4a—C11a—C113.5 (2)O3'''—C3a'''—C7a'''—O1'''0.5 (2)
C2—C1—C11a—C4a3.5 (2)C2'''—O1'''—C7a'''—C7'''174.9 (3)
C2—C1—C11a—C11177.9 (2)C2'''—O1'''—C7a'''—C3a'''6.2 (3)
N10—C11—C11a—C4a46.5 (2)

Experimental details

Crystal data
Chemical formulaC25H23ClN4O2
Mr446.92
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.097 (2), 16.169 (2), 10.752 (2)
β (°) 95.818 (12)
V3)2265.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.60 × 0.57 × 0.53
Data collection
DiffractometerEnraf-Nonius CAD-4 MACHS
diffractometer
Absorption correctionGaussian
(SHELX76; Sheldrick, 1976)
Tmin, Tmax0.893, 0.918
No. of measured, independent and
observed [I > 2σ(I)] reflections
6392, 5171, 3884
Rint0.012
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.097, 1.03
No. of reflections5169
No. of parameters382
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.18, 0.25

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, PROCESS_DATA (Gable et al., 1993), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), ORTEPII (Johnson, 1976), SHELXL93.

Selected geometric parameters (Å, º) top
Cl—C81.740 (2)N1'—C6'1.464 (2)
N5—C5a1.415 (2)N4'—C3'1.457 (2)
N5—C4a1.418 (2)N4'—C5'1.459 (2)
N10—C111.293 (2)N4'—C1''1.463 (2)
N10—C9a1.403 (2)C4a—C11a1.394 (2)
N1'—C111.363 (2)C5a—C9a1.406 (2)
N1'—C2'1.462 (2)C11—C11a1.489 (2)
C5a—N5—C4a114.25 (13)C5'—N4'—C1''111.91 (13)
C11—N10—C9a123.24 (12)C4—C4a—N5121.0 (2)
C11—N1'—C2'120.69 (12)C6—C5a—N5121.42 (14)
C11—N1'—C6'125.19 (13)C8—C9—C9a121.22 (14)
C2'—N1'—C6'111.27 (13)N10—C11—N1'118.19 (13)
C3'—N4'—C5'109.66 (12)N10—C11—C11a125.33 (13)
C3'—N4'—C1''109.87 (13)N1'—C11—C11a116.18 (12)
C5a—N5—C4a—C11a64.0 (2)C6'—N1'—C11—C11a32.6 (2)
C4a—N5—C5a—C9a61.1 (2)N5—C4a—C11a—C113.5 (2)
C11—N10—C9a—C5a41.4 (2)N10—C11—C11a—C4a46.5 (2)
N5—C5a—C9a—N109.1 (2)C3'—N4'—C1''—C5'''70.2 (2)
C9a—N10—C11—C11a6.4 (2)C5'—N4'—C1''—C5'''167.71 (14)
C2'—N1'—C11—N105.9 (2)N4'—C1''—C5'''—C6'''138.3 (2)
C6'—N1'—C11—N10153.3 (2)N4'—C1''—C5'''—C4'''42.8 (2)
C2'—N1'—C11—C11a168.2 (2)
 

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