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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
CCDC reference: 262428
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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-5
H-dibenzo[b,e][1,4]diazepin-11-yl)-
1-methylhexahydropyrazin-1-ium dichloromethane solvate
top
Crystal data top
C25H23Cl2N5O·CH2Cl2 | F(000) = 1168 |
Mr = 565.31 | Dx = 1.46 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 42938 reflections |
a = 14.1386 (2) Å | θ = 3–30° |
b = 9.9659 (1) Å | µ = 0.49 mm−1 |
c = 18.2523 (3) Å | T = 123 K |
β = 90.2765 (5)° | Acicular, yellow |
V = 2571.79 (6) Å3 | 0.35 × 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 scans | θmax = 30.0°, θmin = 3.0° |
41694 measured reflections | h = −19→19 |
7441 independent reflections | k = −13→12 |
4972 reflections with I > 2σ(I) | l = −25→25 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.02 | Δρmax = 0.58 e Å−3 |
7441 reflections | Δρmin = −0.74 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.34345 (14) | 0.57370 (19) | 0.16548 (11) | 0.0166 (4) | |
C2 | 0.36519 (14) | 0.67588 (19) | 0.21372 (11) | 0.0157 (4) | |
H2 | 0.3252 | 0.6927 | 0.2544 | 0.019* | |
C3 | 0.44580 (13) | 0.75492 (18) | 0.20316 (10) | 0.0126 (4) | |
C4 | 0.50372 (13) | 0.72724 (18) | 0.14266 (11) | 0.0136 (4) | |
C5 | 0.48043 (14) | 0.62251 (18) | 0.09509 (11) | 0.0156 (4) | |
H5 | 0.5201 | 0.6042 | 0.0544 | 0.019* | |
C6 | 0.40054 (14) | 0.54492 (19) | 0.10620 (11) | 0.0171 (4) | |
H6 | 0.3853 | 0.4734 | 0.0738 | 0.02* | |
C7 | 0.57366 (13) | 0.94168 (19) | 0.12127 (11) | 0.0136 (4) | |
C8 | 0.60193 (14) | 1.0028 (2) | 0.05622 (11) | 0.0174 (4) | |
H8 | 0.6325 | 0.9512 | 0.0195 | 0.021* | |
C9 | 0.58571 (15) | 1.1379 (2) | 0.04501 (11) | 0.0199 (4) | |
H9 | 0.6064 | 1.1793 | 0.001 | 0.024* | |
C10 | 0.53941 (15) | 1.2134 (2) | 0.09746 (12) | 0.0207 (5) | |
H10 | 0.5258 | 1.3054 | 0.0886 | 0.025* | |
C11 | 0.51306 (14) | 1.15421 (19) | 0.16277 (11) | 0.0179 (4) | |
H11 | 0.4817 | 1.2062 | 0.1989 | 0.021* | |
C12 | 0.53197 (13) | 1.01850 (18) | 0.17630 (10) | 0.0134 (4) | |
C13 | 0.51035 (13) | 0.95792 (18) | 0.24864 (10) | 0.0133 (4) | |
C14 | 0.61698 (14) | 1.11399 (19) | 0.31533 (11) | 0.0170 (4) | |
H14A | 0.6059 | 1.1984 | 0.3426 | 0.02* | |
H14B | 0.6398 | 1.1378 | 0.2658 | 0.02* | |
C15 | 0.69233 (14) | 1.0320 (2) | 0.35482 (11) | 0.0171 (4) | |
H15A | 0.7073 | 0.9513 | 0.3254 | 0.02* | |
H15B | 0.7508 | 1.0861 | 0.3595 | 0.02* | |
C16 | 0.49448 (14) | 0.99746 (19) | 0.38074 (10) | 0.0143 (4) | |
H16A | 0.436 | 0.9438 | 0.3746 | 0.017* | |
H16B | 0.4787 | 1.0777 | 0.4102 | 0.017* | |
C17 | 0.56754 (13) | 0.91477 (18) | 0.42143 (11) | 0.0145 (4) | |
H17A | 0.5428 | 0.8911 | 0.4704 | 0.017* | |
H17B | 0.5789 | 0.8303 | 0.3943 | 0.017* | |
C18 | 0.73007 (15) | 0.8951 (2) | 0.46448 (12) | 0.0221 (5) | |
H18A | 0.7924 | 0.9379 | 0.466 | 0.033* | |
H18B | 0.7335 | 0.8127 | 0.4354 | 0.033* | |
H18C | 0.7101 | 0.8733 | 0.5144 | 0.033* | |
C19 | 0.71274 (14) | 1.17942 (18) | 0.49482 (10) | 0.0137 (4) | |
C20 | 0.68653 (14) | 1.29940 (18) | 0.54135 (11) | 0.0147 (4) | |
C21 | 0.59663 (15) | 1.3555 (2) | 0.53998 (12) | 0.0195 (4) | |
H21 | 0.5475 | 1.3127 | 0.513 | 0.023* | |
C22 | 0.57773 (15) | 1.4738 (2) | 0.57762 (12) | 0.0222 (5) | |
H22 | 0.5161 | 1.5118 | 0.5765 | 0.027* | |
C23 | 0.64951 (16) | 1.5354 (2) | 0.61670 (12) | 0.0202 (4) | |
C24 | 0.73886 (15) | 1.4797 (2) | 0.62084 (12) | 0.0213 (4) | |
H24 | 0.7873 | 1.5219 | 0.6488 | 0.026* | |
C25 | 0.75673 (15) | 1.3612 (2) | 0.58354 (11) | 0.0177 (4) | |
H25 | 0.8177 | 1.3214 | 0.5868 | 0.021* | |
Cl1 | 0.24259 (4) | 0.47669 (5) | 0.18045 (3) | 0.02410 (13) | |
Cl2 | 0.62642 (4) | 1.68840 (5) | 0.65948 (3) | 0.03141 (15) | |
N1 | 0.47056 (11) | 0.84316 (15) | 0.26035 (9) | 0.0136 (3) | |
N2 | 0.58846 (11) | 0.80222 (15) | 0.13265 (9) | 0.0146 (3) | |
H1N | 0.62 | 0.7737 | 0.0971 | 0.017* | |
N3 | 0.52781 (11) | 1.04006 (16) | 0.30872 (9) | 0.0143 (3) | |
N4 | 0.65983 (11) | 0.98928 (15) | 0.43028 (9) | 0.0143 (3) | |
N5 | 0.63786 (11) | 1.10421 (15) | 0.47812 (9) | 0.0142 (3) | |
O1 | 0.79799 (9) | 1.16459 (13) | 0.47726 (7) | 0.0171 (3) | |
C26 | 0.88926 (17) | 1.0908 (2) | 0.21372 (13) | 0.0271 (5) | |
H26A | 0.9492 | 1.1174 | 0.19 | 0.033* | |
H26B | 0.8709 | 1.1631 | 0.248 | 0.033* | |
Cl3 | 0.90643 (4) | 0.94086 (5) | 0.26264 (3) | 0.03211 (15) | |
Cl4 | 0.80044 (5) | 1.07122 (7) | 0.14634 (4) | 0.0487 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0142 (10) | 0.0148 (10) | 0.0207 (11) | −0.0044 (7) | −0.0062 (8) | 0.0025 (8) |
C2 | 0.0147 (10) | 0.0163 (10) | 0.0161 (10) | 0.0005 (7) | 0.0004 (8) | −0.0002 (8) |
C3 | 0.0130 (9) | 0.0117 (9) | 0.0132 (10) | 0.0009 (7) | −0.0026 (7) | −0.0004 (7) |
C4 | 0.0138 (10) | 0.0129 (9) | 0.0143 (10) | 0.0017 (7) | −0.0008 (8) | 0.0020 (7) |
C5 | 0.0196 (10) | 0.0133 (9) | 0.0138 (10) | 0.0027 (7) | −0.0006 (8) | −0.0011 (7) |
C6 | 0.0217 (11) | 0.0129 (9) | 0.0166 (10) | 0.0010 (7) | −0.0061 (8) | −0.0014 (8) |
C7 | 0.0112 (9) | 0.0147 (9) | 0.0147 (10) | −0.0009 (7) | −0.0052 (7) | −0.0016 (7) |
C8 | 0.0155 (10) | 0.0229 (10) | 0.0136 (10) | −0.0027 (8) | −0.0011 (8) | −0.0021 (8) |
C9 | 0.0220 (11) | 0.0225 (11) | 0.0151 (10) | −0.0067 (8) | −0.0039 (8) | 0.0049 (8) |
C10 | 0.0250 (12) | 0.0146 (10) | 0.0225 (11) | −0.0021 (8) | −0.0089 (9) | 0.0033 (8) |
C11 | 0.0207 (11) | 0.0157 (10) | 0.0171 (10) | 0.0004 (8) | −0.0044 (8) | −0.0037 (8) |
C12 | 0.0136 (9) | 0.0137 (9) | 0.0130 (10) | −0.0028 (7) | −0.0036 (7) | −0.0012 (7) |
C13 | 0.0113 (9) | 0.0146 (9) | 0.0139 (10) | 0.0027 (7) | −0.0013 (7) | −0.0027 (7) |
C14 | 0.0212 (11) | 0.0169 (10) | 0.0130 (10) | −0.0070 (8) | −0.0004 (8) | −0.0017 (8) |
C15 | 0.0152 (10) | 0.0228 (10) | 0.0133 (10) | −0.0030 (8) | 0.0026 (8) | −0.0036 (8) |
C16 | 0.0137 (10) | 0.0171 (10) | 0.0122 (10) | −0.0015 (7) | 0.0015 (7) | −0.0027 (7) |
C17 | 0.0158 (10) | 0.0137 (9) | 0.0138 (10) | −0.0041 (7) | 0.0010 (8) | −0.0022 (7) |
C18 | 0.0234 (12) | 0.0183 (10) | 0.0243 (12) | 0.0055 (8) | −0.0074 (9) | −0.0022 (9) |
C19 | 0.0159 (10) | 0.0147 (9) | 0.0106 (9) | −0.0005 (7) | −0.0005 (7) | 0.0046 (7) |
C20 | 0.0164 (10) | 0.0145 (9) | 0.0132 (10) | −0.0030 (7) | 0.0005 (8) | 0.0030 (7) |
C21 | 0.0177 (11) | 0.0178 (10) | 0.0229 (11) | −0.0034 (8) | −0.0018 (9) | −0.0016 (8) |
C22 | 0.0191 (11) | 0.0194 (10) | 0.0280 (12) | 0.0042 (8) | 0.0003 (9) | −0.0009 (9) |
C23 | 0.0278 (12) | 0.0139 (10) | 0.0187 (11) | −0.0016 (8) | 0.0035 (9) | −0.0033 (8) |
C24 | 0.0220 (11) | 0.0244 (11) | 0.0175 (11) | −0.0058 (8) | −0.0002 (9) | −0.0041 (9) |
C25 | 0.0171 (10) | 0.0200 (10) | 0.0159 (10) | −0.0012 (8) | 0.0006 (8) | −0.0007 (8) |
Cl1 | 0.0201 (3) | 0.0222 (3) | 0.0299 (3) | −0.00928 (19) | −0.0035 (2) | −0.0009 (2) |
Cl2 | 0.0376 (3) | 0.0202 (3) | 0.0364 (3) | 0.0033 (2) | −0.0012 (3) | −0.0110 (2) |
N1 | 0.0134 (8) | 0.0127 (8) | 0.0146 (8) | 0.0003 (6) | −0.0004 (6) | −0.0031 (6) |
N2 | 0.0148 (8) | 0.0137 (8) | 0.0152 (8) | 0.0009 (6) | 0.0042 (7) | −0.0012 (6) |
N3 | 0.0167 (9) | 0.0158 (8) | 0.0104 (8) | −0.0031 (6) | 0.0008 (6) | −0.0031 (6) |
N4 | 0.0134 (8) | 0.0147 (8) | 0.0149 (8) | 0.0014 (6) | −0.0012 (6) | −0.0027 (6) |
N5 | 0.0158 (9) | 0.0140 (8) | 0.0128 (8) | 0.0004 (6) | 0.0011 (7) | −0.0050 (6) |
O1 | 0.0143 (7) | 0.0198 (7) | 0.0172 (7) | −0.0012 (5) | 0.0018 (6) | 0.0003 (6) |
C26 | 0.0269 (12) | 0.0259 (12) | 0.0285 (13) | −0.0058 (9) | −0.0076 (10) | 0.0010 (10) |
Cl3 | 0.0372 (3) | 0.0217 (3) | 0.0373 (3) | 0.0053 (2) | −0.0080 (3) | −0.0010 (2) |
Cl4 | 0.0470 (4) | 0.0488 (4) | 0.0499 (4) | −0.0179 (3) | −0.0292 (3) | 0.0150 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.380 (3) | C15—H15B | 0.99 |
C1—C6 | 1.383 (3) | C16—N3 | 1.462 (2) |
C1—Cl1 | 1.745 (2) | C16—C17 | 1.513 (3) |
C2—C3 | 1.400 (3) | C16—H16A | 0.99 |
C2—H2 | 0.95 | C16—H16B | 0.99 |
C3—C4 | 1.405 (3) | C17—N4 | 1.509 (2) |
C3—N1 | 1.408 (2) | C17—H17A | 0.99 |
C4—C5 | 1.396 (3) | C17—H17B | 0.99 |
C4—N2 | 1.425 (2) | C18—N4 | 1.500 (2) |
C5—C6 | 1.385 (3) | C18—H18A | 0.98 |
C5—H5 | 0.95 | C18—H18B | 0.98 |
C6—H6 | 0.95 | C18—H18C | 0.98 |
C7—C8 | 1.395 (3) | C19—O1 | 1.257 (2) |
C7—C12 | 1.396 (3) | C19—N5 | 1.331 (2) |
C7—N2 | 1.421 (2) | C19—C20 | 1.514 (3) |
C8—C9 | 1.381 (3) | C20—C21 | 1.389 (3) |
C8—H8 | 0.95 | C20—C25 | 1.396 (3) |
C9—C10 | 1.385 (3) | C21—C22 | 1.391 (3) |
C9—H9 | 0.95 | C21—H21 | 0.95 |
C10—C11 | 1.383 (3) | C22—C23 | 1.381 (3) |
C10—H10 | 0.95 | C22—H22 | 0.95 |
C11—C12 | 1.400 (3) | C23—C24 | 1.382 (3) |
C11—H11 | 0.95 | C23—Cl2 | 1.744 (2) |
C12—C13 | 1.485 (3) | C24—C25 | 1.387 (3) |
C13—N1 | 1.293 (2) | C24—H24 | 0.95 |
C13—N3 | 1.390 (2) | C25—H25 | 0.95 |
C14—N3 | 1.465 (2) | N2—H1N | 0.8389 |
C14—C15 | 1.522 (3) | N4—N5 | 1.474 (2) |
C14—H14A | 0.99 | C26—Cl3 | 1.757 (2) |
C14—H14B | 0.99 | C26—Cl4 | 1.764 (2) |
C15—N4 | 1.515 (3) | C26—H26A | 0.99 |
C15—H15A | 0.99 | C26—H26B | 0.99 |
| | | |
C2—C1—C6 | 121.55 (18) | C17—C16—H16B | 109.2 |
C2—C1—Cl1 | 119.25 (16) | H16A—C16—H16B | 107.9 |
C6—C1—Cl1 | 119.20 (15) | N4—C17—C16 | 111.86 (15) |
C1—C2—C3 | 120.43 (19) | N4—C17—H17A | 109.2 |
C1—C2—H2 | 119.8 | C16—C17—H17A | 109.2 |
C3—C2—H2 | 119.8 | N4—C17—H17B | 109.2 |
C2—C3—C4 | 118.41 (17) | C16—C17—H17B | 109.2 |
C2—C3—N1 | 116.70 (17) | H17A—C17—H17B | 107.9 |
C4—C3—N1 | 124.16 (17) | N4—C18—H18A | 109.5 |
C5—C4—C3 | 119.92 (18) | N4—C18—H18B | 109.5 |
C5—C4—N2 | 120.57 (17) | H18A—C18—H18B | 109.5 |
C3—C4—N2 | 119.43 (17) | N4—C18—H18C | 109.5 |
C6—C5—C4 | 121.11 (19) | H18A—C18—H18C | 109.5 |
C6—C5—H5 | 119.4 | H18B—C18—H18C | 109.5 |
C4—C5—H5 | 119.4 | O1—C19—N5 | 129.62 (18) |
C1—C6—C5 | 118.57 (18) | O1—C19—C20 | 118.26 (17) |
C1—C6—H6 | 120.7 | N5—C19—C20 | 112.12 (16) |
C5—C6—H6 | 120.7 | C21—C20—C25 | 118.72 (18) |
C8—C7—C12 | 119.81 (17) | C21—C20—C19 | 122.32 (17) |
C8—C7—N2 | 120.59 (17) | C25—C20—C19 | 118.83 (17) |
C12—C7—N2 | 119.59 (17) | C20—C21—C22 | 120.70 (19) |
C9—C8—C7 | 120.24 (19) | C20—C21—H21 | 119.7 |
C9—C8—H8 | 119.9 | C22—C21—H21 | 119.7 |
C7—C8—H8 | 119.9 | C23—C22—C21 | 119.29 (19) |
C8—C9—C10 | 120.43 (19) | C23—C22—H22 | 120.4 |
C8—C9—H9 | 119.8 | C21—C22—H22 | 120.4 |
C10—C9—H9 | 119.8 | C22—C23—C24 | 121.25 (19) |
C11—C10—C9 | 119.60 (19) | C22—C23—Cl2 | 118.74 (16) |
C11—C10—H10 | 120.2 | C24—C23—Cl2 | 119.99 (16) |
C9—C10—H10 | 120.2 | C23—C24—C25 | 118.96 (19) |
C10—C11—C12 | 120.81 (19) | C23—C24—H24 | 120.5 |
C10—C11—H11 | 119.6 | C25—C24—H24 | 120.5 |
C12—C11—H11 | 119.6 | C24—C25—C20 | 121.02 (19) |
C7—C12—C11 | 118.93 (18) | C24—C25—H25 | 119.5 |
C7—C12—C13 | 120.42 (16) | C20—C25—H25 | 119.5 |
C11—C12—C13 | 120.63 (17) | C13—N1—C3 | 122.47 (17) |
N1—C13—N3 | 117.81 (17) | C7—N2—C4 | 114.11 (15) |
N1—C13—C12 | 126.74 (17) | C7—N2—H1N | 107.3 |
N3—C13—C12 | 115.19 (16) | C4—N2—H1N | 111.8 |
N3—C14—C15 | 111.67 (16) | C13—N3—C16 | 118.80 (16) |
N3—C14—H14A | 109.3 | C13—N3—C14 | 120.73 (16) |
C15—C14—H14A | 109.3 | C16—N3—C14 | 110.69 (15) |
N3—C14—H14B | 109.3 | N5—N4—C18 | 112.36 (15) |
C15—C14—H14B | 109.3 | N5—N4—C17 | 105.13 (14) |
H14A—C14—H14B | 107.9 | C18—N4—C17 | 107.88 (15) |
N4—C15—C14 | 111.52 (16) | N5—N4—C15 | 112.70 (14) |
N4—C15—H15A | 109.3 | C18—N4—C15 | 110.54 (15) |
C14—C15—H15A | 109.3 | C17—N4—C15 | 107.87 (14) |
N4—C15—H15B | 109.3 | C19—N5—N4 | 113.79 (15) |
C14—C15—H15B | 109.3 | Cl3—C26—Cl4 | 110.86 (12) |
H15A—C15—H15B | 108 | Cl3—C26—H26A | 109.5 |
N3—C16—C17 | 112.16 (16) | Cl4—C26—H26A | 109.5 |
N3—C16—H16A | 109.2 | Cl3—C26—H26B | 109.5 |
C17—C16—H16A | 109.2 | Cl4—C26—H26B | 109.5 |
N3—C16—H16B | 109.2 | H26A—C26—H26B | 108.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N···O1i | 0.84 | 2.09 | 2.918 (2) | 167 |
Symmetry code: (i) −x+3/2, y−1/2, −z+1/2. |
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