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The structure of the title compound, C25H23Cl2N5O·CH2Cl2, confirms the presence of 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 aromatic rings being similar to that found for the parent compound, clozapine and related structures. The piperazine ring displays an almost perfect chair conformation, with the methyl and chloro­benz­imide groups assuming equatorial and axial orientations, respectively, at the cationic nitro­gen site. At the other piperazine N atom, the dibenzodiazepine nucleus assumes an axial orientation. The relative positions 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/S1600536804031095/hg6118sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031095/hg6118Isup2.hkl
Contains datablock I

CCDC reference: 262428

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.111
  • Data-to-parameter ratio = 22.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT374_ALERT_2_A Long N - N Bond N4 - N5 ... 1.47 Ang.
Author Response: This is not an atypical bond length for a N-N zwitterion, see for example Cambridge data base entries BEDJOJ, GILYIJ, PABDIF, QOMBAV, TMABZA10, WEFHAQ, IPADAE and IPADEI.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Bruker, 1997–2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(4-Chlorobenzoylamino)-4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)- 1-methylhexahydropyrazin-1-ium dichloromethane solvate top
Crystal data top
C25H23Cl2N5O·CH2Cl2F(000) = 1168
Mr = 565.31Dx = 1.46 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 42938 reflections
a = 14.1386 (2) Åθ = 3–30°
b = 9.9659 (1) ŵ = 0.49 mm1
c = 18.2523 (3) ÅT = 123 K
β = 90.2765 (5)°Acicular, yellow
V = 2571.79 (6) Å30.35 × 0.08 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
Rint = 0.070
CCD rotation images, thick–slice π and ω scansθmax = 30.0°, θmin = 3.0°
41694 measured reflectionsh = 1919
7441 independent reflectionsk = 1312
4972 reflections with I > 2σ(I)l = 2525
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0419P)2 + 1.7861P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.58 e Å3
7441 reflectionsΔρmin = 0.74 e Å3
326 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.34345 (14)0.57370 (19)0.16548 (11)0.0166 (4)
C20.36519 (14)0.67588 (19)0.21372 (11)0.0157 (4)
H20.32520.69270.25440.019*
C30.44580 (13)0.75492 (18)0.20316 (10)0.0126 (4)
C40.50372 (13)0.72724 (18)0.14266 (11)0.0136 (4)
C50.48043 (14)0.62251 (18)0.09509 (11)0.0156 (4)
H50.52010.60420.05440.019*
C60.40054 (14)0.54492 (19)0.10620 (11)0.0171 (4)
H60.38530.47340.07380.02*
C70.57366 (13)0.94168 (19)0.12127 (11)0.0136 (4)
C80.60193 (14)1.0028 (2)0.05622 (11)0.0174 (4)
H80.63250.95120.01950.021*
C90.58571 (15)1.1379 (2)0.04501 (11)0.0199 (4)
H90.60641.17930.0010.024*
C100.53941 (15)1.2134 (2)0.09746 (12)0.0207 (5)
H100.52581.30540.08860.025*
C110.51306 (14)1.15421 (19)0.16277 (11)0.0179 (4)
H110.48171.20620.19890.021*
C120.53197 (13)1.01850 (18)0.17630 (10)0.0134 (4)
C130.51035 (13)0.95792 (18)0.24864 (10)0.0133 (4)
C140.61698 (14)1.11399 (19)0.31533 (11)0.0170 (4)
H14A0.60591.19840.34260.02*
H14B0.63981.13780.26580.02*
C150.69233 (14)1.0320 (2)0.35482 (11)0.0171 (4)
H15A0.70730.95130.32540.02*
H15B0.75081.08610.35950.02*
C160.49448 (14)0.99746 (19)0.38074 (10)0.0143 (4)
H16A0.4360.94380.37460.017*
H16B0.47871.07770.41020.017*
C170.56754 (13)0.91477 (18)0.42143 (11)0.0145 (4)
H17A0.54280.89110.47040.017*
H17B0.57890.83030.39430.017*
C180.73007 (15)0.8951 (2)0.46448 (12)0.0221 (5)
H18A0.79240.93790.4660.033*
H18B0.73350.81270.43540.033*
H18C0.71010.87330.51440.033*
C190.71274 (14)1.17942 (18)0.49482 (10)0.0137 (4)
C200.68653 (14)1.29940 (18)0.54135 (11)0.0147 (4)
C210.59663 (15)1.3555 (2)0.53998 (12)0.0195 (4)
H210.54751.31270.5130.023*
C220.57773 (15)1.4738 (2)0.57762 (12)0.0222 (5)
H220.51611.51180.57650.027*
C230.64951 (16)1.5354 (2)0.61670 (12)0.0202 (4)
C240.73886 (15)1.4797 (2)0.62084 (12)0.0213 (4)
H240.78731.52190.64880.026*
C250.75673 (15)1.3612 (2)0.58354 (11)0.0177 (4)
H250.81771.32140.58680.021*
Cl10.24259 (4)0.47669 (5)0.18045 (3)0.02410 (13)
Cl20.62642 (4)1.68840 (5)0.65948 (3)0.03141 (15)
N10.47056 (11)0.84316 (15)0.26035 (9)0.0136 (3)
N20.58846 (11)0.80222 (15)0.13265 (9)0.0146 (3)
H1N0.620.77370.09710.017*
N30.52781 (11)1.04006 (16)0.30872 (9)0.0143 (3)
N40.65983 (11)0.98928 (15)0.43028 (9)0.0143 (3)
N50.63786 (11)1.10421 (15)0.47812 (9)0.0142 (3)
O10.79799 (9)1.16459 (13)0.47726 (7)0.0171 (3)
C260.88926 (17)1.0908 (2)0.21372 (13)0.0271 (5)
H26A0.94921.11740.190.033*
H26B0.87091.16310.2480.033*
Cl30.90643 (4)0.94086 (5)0.26264 (3)0.03211 (15)
Cl40.80044 (5)1.07122 (7)0.14634 (4)0.0487 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0142 (10)0.0148 (10)0.0207 (11)0.0044 (7)0.0062 (8)0.0025 (8)
C20.0147 (10)0.0163 (10)0.0161 (10)0.0005 (7)0.0004 (8)0.0002 (8)
C30.0130 (9)0.0117 (9)0.0132 (10)0.0009 (7)0.0026 (7)0.0004 (7)
C40.0138 (10)0.0129 (9)0.0143 (10)0.0017 (7)0.0008 (8)0.0020 (7)
C50.0196 (10)0.0133 (9)0.0138 (10)0.0027 (7)0.0006 (8)0.0011 (7)
C60.0217 (11)0.0129 (9)0.0166 (10)0.0010 (7)0.0061 (8)0.0014 (8)
C70.0112 (9)0.0147 (9)0.0147 (10)0.0009 (7)0.0052 (7)0.0016 (7)
C80.0155 (10)0.0229 (10)0.0136 (10)0.0027 (8)0.0011 (8)0.0021 (8)
C90.0220 (11)0.0225 (11)0.0151 (10)0.0067 (8)0.0039 (8)0.0049 (8)
C100.0250 (12)0.0146 (10)0.0225 (11)0.0021 (8)0.0089 (9)0.0033 (8)
C110.0207 (11)0.0157 (10)0.0171 (10)0.0004 (8)0.0044 (8)0.0037 (8)
C120.0136 (9)0.0137 (9)0.0130 (10)0.0028 (7)0.0036 (7)0.0012 (7)
C130.0113 (9)0.0146 (9)0.0139 (10)0.0027 (7)0.0013 (7)0.0027 (7)
C140.0212 (11)0.0169 (10)0.0130 (10)0.0070 (8)0.0004 (8)0.0017 (8)
C150.0152 (10)0.0228 (10)0.0133 (10)0.0030 (8)0.0026 (8)0.0036 (8)
C160.0137 (10)0.0171 (10)0.0122 (10)0.0015 (7)0.0015 (7)0.0027 (7)
C170.0158 (10)0.0137 (9)0.0138 (10)0.0041 (7)0.0010 (8)0.0022 (7)
C180.0234 (12)0.0183 (10)0.0243 (12)0.0055 (8)0.0074 (9)0.0022 (9)
C190.0159 (10)0.0147 (9)0.0106 (9)0.0005 (7)0.0005 (7)0.0046 (7)
C200.0164 (10)0.0145 (9)0.0132 (10)0.0030 (7)0.0005 (8)0.0030 (7)
C210.0177 (11)0.0178 (10)0.0229 (11)0.0034 (8)0.0018 (9)0.0016 (8)
C220.0191 (11)0.0194 (10)0.0280 (12)0.0042 (8)0.0003 (9)0.0009 (9)
C230.0278 (12)0.0139 (10)0.0187 (11)0.0016 (8)0.0035 (9)0.0033 (8)
C240.0220 (11)0.0244 (11)0.0175 (11)0.0058 (8)0.0002 (9)0.0041 (9)
C250.0171 (10)0.0200 (10)0.0159 (10)0.0012 (8)0.0006 (8)0.0007 (8)
Cl10.0201 (3)0.0222 (3)0.0299 (3)0.00928 (19)0.0035 (2)0.0009 (2)
Cl20.0376 (3)0.0202 (3)0.0364 (3)0.0033 (2)0.0012 (3)0.0110 (2)
N10.0134 (8)0.0127 (8)0.0146 (8)0.0003 (6)0.0004 (6)0.0031 (6)
N20.0148 (8)0.0137 (8)0.0152 (8)0.0009 (6)0.0042 (7)0.0012 (6)
N30.0167 (9)0.0158 (8)0.0104 (8)0.0031 (6)0.0008 (6)0.0031 (6)
N40.0134 (8)0.0147 (8)0.0149 (8)0.0014 (6)0.0012 (6)0.0027 (6)
N50.0158 (9)0.0140 (8)0.0128 (8)0.0004 (6)0.0011 (7)0.0050 (6)
O10.0143 (7)0.0198 (7)0.0172 (7)0.0012 (5)0.0018 (6)0.0003 (6)
C260.0269 (12)0.0259 (12)0.0285 (13)0.0058 (9)0.0076 (10)0.0010 (10)
Cl30.0372 (3)0.0217 (3)0.0373 (3)0.0053 (2)0.0080 (3)0.0010 (2)
Cl40.0470 (4)0.0488 (4)0.0499 (4)0.0179 (3)0.0292 (3)0.0150 (3)
Geometric parameters (Å, º) top
C1—C21.380 (3)C15—H15B0.99
C1—C61.383 (3)C16—N31.462 (2)
C1—Cl11.745 (2)C16—C171.513 (3)
C2—C31.400 (3)C16—H16A0.99
C2—H20.95C16—H16B0.99
C3—C41.405 (3)C17—N41.509 (2)
C3—N11.408 (2)C17—H17A0.99
C4—C51.396 (3)C17—H17B0.99
C4—N21.425 (2)C18—N41.500 (2)
C5—C61.385 (3)C18—H18A0.98
C5—H50.95C18—H18B0.98
C6—H60.95C18—H18C0.98
C7—C81.395 (3)C19—O11.257 (2)
C7—C121.396 (3)C19—N51.331 (2)
C7—N21.421 (2)C19—C201.514 (3)
C8—C91.381 (3)C20—C211.389 (3)
C8—H80.95C20—C251.396 (3)
C9—C101.385 (3)C21—C221.391 (3)
C9—H90.95C21—H210.95
C10—C111.383 (3)C22—C231.381 (3)
C10—H100.95C22—H220.95
C11—C121.400 (3)C23—C241.382 (3)
C11—H110.95C23—Cl21.744 (2)
C12—C131.485 (3)C24—C251.387 (3)
C13—N11.293 (2)C24—H240.95
C13—N31.390 (2)C25—H250.95
C14—N31.465 (2)N2—H1N0.8389
C14—C151.522 (3)N4—N51.474 (2)
C14—H14A0.99C26—Cl31.757 (2)
C14—H14B0.99C26—Cl41.764 (2)
C15—N41.515 (3)C26—H26A0.99
C15—H15A0.99C26—H26B0.99
C2—C1—C6121.55 (18)C17—C16—H16B109.2
C2—C1—Cl1119.25 (16)H16A—C16—H16B107.9
C6—C1—Cl1119.20 (15)N4—C17—C16111.86 (15)
C1—C2—C3120.43 (19)N4—C17—H17A109.2
C1—C2—H2119.8C16—C17—H17A109.2
C3—C2—H2119.8N4—C17—H17B109.2
C2—C3—C4118.41 (17)C16—C17—H17B109.2
C2—C3—N1116.70 (17)H17A—C17—H17B107.9
C4—C3—N1124.16 (17)N4—C18—H18A109.5
C5—C4—C3119.92 (18)N4—C18—H18B109.5
C5—C4—N2120.57 (17)H18A—C18—H18B109.5
C3—C4—N2119.43 (17)N4—C18—H18C109.5
C6—C5—C4121.11 (19)H18A—C18—H18C109.5
C6—C5—H5119.4H18B—C18—H18C109.5
C4—C5—H5119.4O1—C19—N5129.62 (18)
C1—C6—C5118.57 (18)O1—C19—C20118.26 (17)
C1—C6—H6120.7N5—C19—C20112.12 (16)
C5—C6—H6120.7C21—C20—C25118.72 (18)
C8—C7—C12119.81 (17)C21—C20—C19122.32 (17)
C8—C7—N2120.59 (17)C25—C20—C19118.83 (17)
C12—C7—N2119.59 (17)C20—C21—C22120.70 (19)
C9—C8—C7120.24 (19)C20—C21—H21119.7
C9—C8—H8119.9C22—C21—H21119.7
C7—C8—H8119.9C23—C22—C21119.29 (19)
C8—C9—C10120.43 (19)C23—C22—H22120.4
C8—C9—H9119.8C21—C22—H22120.4
C10—C9—H9119.8C22—C23—C24121.25 (19)
C11—C10—C9119.60 (19)C22—C23—Cl2118.74 (16)
C11—C10—H10120.2C24—C23—Cl2119.99 (16)
C9—C10—H10120.2C23—C24—C25118.96 (19)
C10—C11—C12120.81 (19)C23—C24—H24120.5
C10—C11—H11119.6C25—C24—H24120.5
C12—C11—H11119.6C24—C25—C20121.02 (19)
C7—C12—C11118.93 (18)C24—C25—H25119.5
C7—C12—C13120.42 (16)C20—C25—H25119.5
C11—C12—C13120.63 (17)C13—N1—C3122.47 (17)
N1—C13—N3117.81 (17)C7—N2—C4114.11 (15)
N1—C13—C12126.74 (17)C7—N2—H1N107.3
N3—C13—C12115.19 (16)C4—N2—H1N111.8
N3—C14—C15111.67 (16)C13—N3—C16118.80 (16)
N3—C14—H14A109.3C13—N3—C14120.73 (16)
C15—C14—H14A109.3C16—N3—C14110.69 (15)
N3—C14—H14B109.3N5—N4—C18112.36 (15)
C15—C14—H14B109.3N5—N4—C17105.13 (14)
H14A—C14—H14B107.9C18—N4—C17107.88 (15)
N4—C15—C14111.52 (16)N5—N4—C15112.70 (14)
N4—C15—H15A109.3C18—N4—C15110.54 (15)
C14—C15—H15A109.3C17—N4—C15107.87 (14)
N4—C15—H15B109.3C19—N5—N4113.79 (15)
C14—C15—H15B109.3Cl3—C26—Cl4110.86 (12)
H15A—C15—H15B108Cl3—C26—H26A109.5
N3—C16—C17112.16 (16)Cl4—C26—H26A109.5
N3—C16—H16A109.2Cl3—C26—H26B109.5
C17—C16—H16A109.2Cl4—C26—H26B109.5
N3—C16—H16B109.2H26A—C26—H26B108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N···O1i0.842.092.918 (2)167
Symmetry code: (i) x+3/2, y1/2, z+1/2.
 

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