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The centrosymmetric title compound, C28H20Cl2N6O2, features a tricyclic framework with the characteristic V-shape of the pyridobenzoxazepine nucleus and with the central seven-membered heterocycle having a classical boat conformation. The piperazine ring displays an almost-perfect chair conformation, with the tricyclic nuclei assuming a pseudo-equatorial orientation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604520X/tk2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604520X/tk2092Isup2.hkl
Contains datablock I

CCDC reference: 630487

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.040
  • wR factor = 0.104
  • Data-to-parameter ratio = 16.6

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Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The work described in this contribution is part of a multi-disciplinary research program. The synthesis and characteristaion of compound was performed by Amelia Vom under the combined supervision of Ben Capuano, Edward J. Lloyd, Ian Crosby and Elizabeth Yuriev. The crystallographic analysis was performed by Craig M. Forsyth.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Bruker, 2004); cell refinement: HKL-2000 (Bruker, 2004); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and POV-RAY (Cason, 2003); software used to prepare material for publication: SHELXL97.

5,5'-(Piperazine-1,4-diyl)bis(8-chloropyrido[2,3-b][1,5]benzoxazepine) top
Crystal data top
C28H20Cl2N6O2F(000) = 560
Mr = 543.40Dx = 1.451 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13486 reflections
a = 8.6940 (2) Åθ = 2.4–27.5°
b = 8.9993 (2) ŵ = 0.30 mm1
c = 16.2542 (4) ÅT = 123 K
β = 102.089 (1)°Prismatic, pale yellow
V = 1243.52 (5) Å30.20 × 0.10 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius KappaCCD area-detector
diffractometer
2860 independent reflections
Radiation source: fine-focus sealed tube2080 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
1° frames in φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SORTAV; Blessing 1997)
h = 1111
Tmin = 0.932, Tmax = 0.971k = 1110
13846 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2669P]
where P = (Fo2 + 2Fc2)/3
2860 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Experimental. Spectroscopic analysis: IR (Medium?, νmax, cm-1): 1599, 1586, 1549; 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 3.66 (8H, br s, H2', H3', H5', H6'), 6.99 (2H, δ, J = 8.5 Hz, H9, H9''), 7.17–7.28 (6H, m, H3, H7, H10, H3'', H7'', H10''), 7.77 (2H, d, J = 7.5 Hz, H4, H4''), 8.45 (2H, br s, H2, H2''); 13C NMR (75.5 MHz, CDCl3, δ, p.p.m.): 47.4 (CH2), 117.4 (Cq), 121.9 (CH), 122.4 (CH), 125.0 (CH), 126.7 (CH), 131.1 (Cq), 139.7 (CH), 140.1 (Cq), 148.5 (Cq), 151.9 (CH), 158.2 (Cq), 164.2 (Cq); ESI MS (70 V): m/z 545 (M[37Cl]H+, 34%), 543 (M[35Cl]H+, 100), 274 (26), 272 (80). ESI high-resolution MS, found: m/z 543.1088, calculated for C28H20Cl2N6O2: m/z 543.1098.

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
Cl10.49521 (6)0.71604 (5)0.02155 (3)0.03145 (16)
O10.99081 (14)1.13592 (13)0.17585 (7)0.0217 (3)
N11.25115 (18)1.08117 (17)0.18770 (9)0.0248 (4)
N20.83072 (17)0.95762 (15)0.28097 (8)0.0189 (3)
N30.99236 (17)0.97728 (16)0.41237 (8)0.0187 (3)
C10.6392 (2)0.8438 (2)0.06698 (11)0.0224 (4)
C20.7095 (2)0.9313 (2)0.01586 (11)0.0252 (4)
H20.67770.92600.04370.030*
C30.8281 (2)1.0276 (2)0.05378 (11)0.0239 (4)
H30.87841.08940.02000.029*
C40.8735 (2)1.03400 (19)0.14064 (10)0.0201 (4)
C50.8019 (2)0.94623 (19)0.19280 (10)0.0185 (4)
C60.6819 (2)0.84989 (19)0.15396 (10)0.0196 (4)
H60.62990.78880.18720.024*
C71.1243 (2)1.06428 (18)0.21942 (10)0.0193 (4)
C81.1177 (2)0.98549 (18)0.29244 (10)0.0177 (4)
C91.2552 (2)0.91402 (19)0.33230 (10)0.0218 (4)
H91.25630.85530.38100.026*
C101.3907 (2)0.9289 (2)0.30051 (11)0.0268 (4)
H101.48580.88120.32670.032*
C111.3827 (2)1.0154 (2)0.22958 (12)0.0281 (4)
H111.47651.02920.20920.034*
C120.9706 (2)0.97694 (18)0.32529 (10)0.0172 (4)
C130.8552 (2)0.9442 (2)0.44828 (10)0.0213 (4)
H13A0.79580.85990.41780.026*
H13B0.78471.03170.44240.026*
C141.0901 (2)1.09491 (19)0.45951 (10)0.0206 (4)
H14A1.02901.18850.45460.025*
H14B1.18311.11180.43440.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0278 (3)0.0355 (3)0.0253 (3)0.0012 (2)0.00746 (18)0.0094 (2)
O10.0221 (7)0.0207 (6)0.0210 (6)0.0020 (5)0.0016 (5)0.0038 (5)
N10.0267 (9)0.0292 (9)0.0204 (8)0.0032 (7)0.0095 (6)0.0005 (6)
N20.0207 (8)0.0216 (8)0.0138 (7)0.0003 (6)0.0023 (6)0.0020 (6)
N30.0202 (8)0.0238 (8)0.0124 (7)0.0070 (6)0.0041 (6)0.0030 (6)
C10.0202 (9)0.0244 (9)0.0197 (9)0.0065 (7)0.0027 (7)0.0040 (7)
C20.0288 (10)0.0303 (10)0.0139 (8)0.0108 (8)0.0012 (7)0.0010 (7)
C30.0262 (10)0.0282 (10)0.0175 (9)0.0086 (8)0.0051 (7)0.0050 (7)
C40.0206 (9)0.0195 (9)0.0193 (9)0.0061 (7)0.0024 (7)0.0003 (7)
C50.0193 (9)0.0211 (9)0.0151 (8)0.0060 (7)0.0032 (7)0.0005 (7)
C60.0188 (9)0.0223 (9)0.0172 (8)0.0030 (7)0.0023 (7)0.0016 (7)
C70.0214 (9)0.0198 (9)0.0162 (8)0.0019 (7)0.0030 (7)0.0034 (7)
C80.0207 (9)0.0182 (8)0.0138 (8)0.0007 (7)0.0027 (7)0.0029 (7)
C90.0245 (10)0.0246 (9)0.0150 (8)0.0004 (7)0.0012 (7)0.0008 (7)
C100.0228 (10)0.0332 (11)0.0233 (9)0.0058 (8)0.0022 (8)0.0018 (8)
C110.0234 (10)0.0352 (11)0.0281 (10)0.0037 (8)0.0108 (8)0.0006 (8)
C120.0223 (9)0.0157 (8)0.0139 (8)0.0007 (7)0.0045 (7)0.0006 (7)
C130.0201 (9)0.0286 (10)0.0150 (8)0.0075 (7)0.0033 (7)0.0030 (7)
C140.0232 (9)0.0242 (9)0.0149 (8)0.0084 (7)0.0055 (7)0.0042 (7)
Geometric parameters (Å, º) top
Cl1—C11.745 (2)C5—C61.401 (2)
O1—C71.386 (2)C6—H60.9500
O1—C41.401 (2)C7—C81.394 (2)
N1—C71.320 (2)C8—C91.392 (2)
N1—C111.340 (2)C8—C121.488 (2)
N2—C121.289 (2)C9—C101.389 (3)
N2—C51.406 (2)C9—H90.9500
N3—C121.388 (2)C10—C111.381 (3)
N3—C131.464 (2)C10—H100.9500
N3—C141.469 (2)C11—H110.9500
C1—C21.378 (3)C13—C14i1.516 (2)
C1—C61.386 (2)C13—H13A0.9900
C2—C31.388 (3)C13—H13B0.9900
C2—H20.9500C14—C13i1.516 (2)
C3—C41.385 (2)C14—H14A0.9900
C3—H30.9500C14—H14B0.9900
C4—C51.397 (2)
C7—O1—C4111.35 (12)C9—C8—C7116.56 (16)
C7—N1—C11116.40 (15)C9—C8—C12121.88 (15)
C12—N2—C5121.72 (14)C7—C8—C12121.56 (15)
C12—N3—C13117.23 (13)C10—C9—C8119.66 (16)
C12—N3—C14118.29 (13)C10—C9—H9120.2
C13—N3—C14111.68 (13)C8—C9—H9120.2
C2—C1—C6122.32 (17)C11—C10—C9117.85 (17)
C2—C1—Cl1119.41 (13)C11—C10—H10121.1
C6—C1—Cl1118.24 (14)C9—C10—H10121.1
C1—C2—C3118.12 (16)N1—C11—C10124.14 (17)
C1—C2—H2120.9N1—C11—H11117.9
C3—C2—H2120.9C10—C11—H11117.9
C4—C3—C2120.34 (17)N2—C12—N3118.79 (15)
C4—C3—H3119.8N2—C12—C8126.01 (14)
C2—C3—H3119.8N3—C12—C8114.94 (14)
C3—C4—C5121.78 (17)N3—C13—C14i109.18 (14)
C3—C4—O1118.11 (16)N3—C13—H13A109.8
C5—C4—O1120.07 (14)C14i—C13—H13A109.8
C4—C5—C6117.45 (15)N3—C13—H13B109.8
C4—C5—N2124.77 (16)C14i—C13—H13B109.8
C6—C5—N2117.49 (15)H13A—C13—H13B108.3
C1—C6—C5119.98 (16)N3—C14—C13i112.08 (14)
C1—C6—H6120.0N3—C14—H14A109.2
C5—C6—H6120.0C13i—C14—H14A109.2
N1—C7—O1115.18 (15)N3—C14—H14B109.2
N1—C7—C8125.28 (16)C13i—C14—H14B109.2
O1—C7—C8119.51 (15)H14A—C14—H14B107.9
Symmetry code: (i) x+2, y+2, z+1.
 

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