The conformation of the title compound, C
18H
21N
5, is very similar to that observed in other diaryldiazepine structures such as clozapine and clozapine dihydrobromide. N—H
H hydrogen-bond interactions result in the formation of a dimer.
Supporting information
CCDC reference: 227905
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.106
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C4 = 5.55 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N12 - C13 = 6.60 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C23 = 6.45 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
8-methyl-6-(4-methylpiperazin-1-yl)-11
H-pyrido[2,3-
b][1,4]benzodiazepine
top
Crystal data top
C18H21N5 | F(000) = 1312 |
Mr = 307.40 | Dx = 1.215 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 21 reflections |
a = 13.0331 (19) Å | θ = 15.2–17.5° |
b = 15.610 (3) Å | µ = 0.08 mm−1 |
c = 16.514 (3) Å | T = 293 K |
V = 3359.7 (10) Å3 | Prismatic, yellow |
Z = 8 | 0.35 × 0.30 × 0.25 mm |
Data collection top
Bruker P4 diffractometer | 1441 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
2θ/ω scans | h = −1→15 |
Absorption correction: ψ scan NORTH et al. (1968) | k = −1→18 |
Tmin = 0.915, Tmax = 0.964 | l = −1→19 |
6621 measured reflections | 3 standard reflections every 97 reflections |
2952 independent reflections | intensity decay: none |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3 |
2952 reflections | (Δ/σ)max < 0.001 |
214 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
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 | 0.1385 (2) | −0.17988 (17) | 0.39975 (17) | 0.0422 (7) | |
C2 | 0.2428 (2) | −0.19645 (19) | 0.40642 (17) | 0.0505 (8) | |
H2 | 0.2665 | −0.2522 | 0.3995 | 0.061* | |
C3 | 0.3117 (2) | −0.13219 (19) | 0.42307 (16) | 0.0485 (8) | |
H3 | 0.3810 | −0.1453 | 0.4283 | 0.058* | |
C4 | 0.27932 (19) | −0.04816 (18) | 0.43214 (15) | 0.0377 (7) | |
N5 | 0.35215 (17) | 0.01730 (15) | 0.45089 (14) | 0.0435 (6) | |
C6 | 0.33915 (19) | 0.05731 (17) | 0.52705 (16) | 0.0375 (7) | |
N7 | 0.42085 (16) | 0.05835 (15) | 0.57517 (14) | 0.0462 (6) | |
C8 | 0.4111 (2) | 0.09548 (17) | 0.64822 (18) | 0.0515 (8) | |
H8 | 0.4684 | 0.0981 | 0.6817 | 0.062* | |
C9 | 0.3207 (2) | 0.12962 (18) | 0.67570 (17) | 0.0506 (8) | |
H9 | 0.3153 | 0.1511 | 0.7280 | 0.061* | |
C10 | 0.2378 (2) | 0.13119 (17) | 0.62343 (18) | 0.0458 (7) | |
H10 | 0.1766 | 0.1564 | 0.6400 | 0.055* | |
C11 | 0.24461 (18) | 0.09568 (16) | 0.54676 (16) | 0.0347 (7) | |
N12 | 0.16467 (15) | 0.11225 (13) | 0.49219 (13) | 0.0377 (6) | |
C13 | 0.13708 (18) | 0.06056 (17) | 0.43574 (16) | 0.0338 (7) | |
C14 | 0.17614 (18) | −0.02847 (16) | 0.42345 (15) | 0.0333 (6) | |
C15 | 0.10745 (19) | −0.09536 (16) | 0.40851 (14) | 0.0374 (7) | |
H15 | 0.0379 | −0.0827 | 0.4043 | 0.045* | |
N16 | 0.05588 (15) | 0.08543 (13) | 0.38767 (12) | 0.0391 (6) | |
C17 | 0.04449 (18) | 0.06192 (18) | 0.30254 (15) | 0.0415 (7) | |
H17A | 0.0801 | 0.0085 | 0.2923 | 0.050* | |
H17B | 0.0750 | 0.1058 | 0.2687 | 0.050* | |
C18 | −0.06735 (18) | 0.05210 (18) | 0.28135 (16) | 0.0461 (7) | |
H18A | −0.0742 | 0.0379 | 0.2244 | 0.055* | |
H18B | −0.0970 | 0.0058 | 0.3128 | 0.055* | |
N19 | −0.12201 (15) | 0.13167 (14) | 0.29836 (13) | 0.0420 (6) | |
C20 | −0.11061 (19) | 0.15301 (17) | 0.38408 (16) | 0.0445 (8) | |
H20A | −0.1399 | 0.1076 | 0.4169 | 0.053* | |
H20B | −0.1476 | 0.2055 | 0.3958 | 0.053* | |
C21 | 0.00017 (19) | 0.16419 (16) | 0.40524 (17) | 0.0436 (7) | |
H21A | 0.0290 | 0.2111 | 0.3741 | 0.052* | |
H21B | 0.0067 | 0.1781 | 0.4623 | 0.052* | |
C22 | −0.23000 (19) | 0.1241 (2) | 0.27616 (19) | 0.0639 (9) | |
H22A | −0.2354 | 0.1089 | 0.2200 | 0.096* | |
H22B | −0.2639 | 0.1778 | 0.2853 | 0.096* | |
H22C | −0.2618 | 0.0805 | 0.3086 | 0.096* | |
C23 | 0.0626 (2) | −0.25075 (17) | 0.38410 (18) | 0.0643 (10) | |
H23A | −0.0055 | −0.2306 | 0.3953 | 0.096* | |
H23B | 0.0780 | −0.2986 | 0.4185 | 0.096* | |
H23C | 0.0670 | −0.2682 | 0.3285 | 0.096* | |
H5 | 0.4185 (14) | −0.0017 (16) | 0.4458 (17) | 0.066 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0485 (18) | 0.0380 (17) | 0.0401 (17) | −0.0017 (14) | 0.0026 (15) | −0.0057 (14) |
C2 | 0.0543 (19) | 0.0424 (18) | 0.055 (2) | 0.0123 (16) | 0.0030 (18) | −0.0049 (16) |
C3 | 0.0400 (16) | 0.0509 (19) | 0.055 (2) | 0.0157 (17) | −0.0052 (16) | −0.0012 (17) |
C4 | 0.0327 (15) | 0.0434 (18) | 0.0369 (16) | −0.0015 (15) | 0.0007 (14) | 0.0022 (14) |
N5 | 0.0319 (14) | 0.0577 (16) | 0.0410 (14) | 0.0058 (13) | 0.0006 (12) | −0.0038 (13) |
C6 | 0.0286 (15) | 0.0425 (16) | 0.0414 (17) | −0.0043 (15) | −0.0044 (14) | 0.0087 (15) |
N7 | 0.0385 (13) | 0.0566 (15) | 0.0433 (15) | −0.0011 (13) | −0.0102 (13) | 0.0037 (13) |
C8 | 0.0477 (19) | 0.0558 (19) | 0.051 (2) | −0.0035 (17) | −0.0164 (17) | 0.0060 (18) |
C9 | 0.0576 (19) | 0.057 (2) | 0.0372 (18) | −0.0008 (17) | −0.0101 (17) | −0.0010 (16) |
C10 | 0.0432 (17) | 0.0447 (18) | 0.0495 (19) | 0.0035 (15) | −0.0043 (16) | −0.0019 (15) |
C11 | 0.0335 (16) | 0.0343 (16) | 0.0363 (16) | −0.0035 (13) | −0.0072 (14) | 0.0041 (13) |
N12 | 0.0351 (13) | 0.0392 (14) | 0.0387 (14) | 0.0038 (12) | −0.0113 (11) | −0.0024 (11) |
C13 | 0.0219 (14) | 0.0415 (16) | 0.0380 (16) | 0.0013 (14) | 0.0024 (13) | 0.0082 (15) |
C14 | 0.0308 (15) | 0.0374 (16) | 0.0318 (15) | 0.0009 (14) | −0.0033 (13) | 0.0005 (13) |
C15 | 0.0359 (15) | 0.0413 (16) | 0.0350 (16) | 0.0051 (14) | −0.0033 (14) | −0.0011 (14) |
N16 | 0.0370 (13) | 0.0445 (13) | 0.0358 (13) | 0.0089 (11) | −0.0101 (12) | −0.0046 (11) |
C17 | 0.0332 (16) | 0.0544 (17) | 0.0368 (17) | 0.0050 (14) | 0.0018 (13) | 0.0025 (15) |
C18 | 0.0386 (16) | 0.0583 (19) | 0.0416 (17) | 0.0004 (16) | −0.0047 (15) | −0.0037 (15) |
N19 | 0.0289 (12) | 0.0510 (14) | 0.0461 (15) | 0.0026 (12) | −0.0066 (12) | 0.0075 (13) |
C20 | 0.0359 (16) | 0.0482 (19) | 0.0494 (19) | 0.0099 (14) | −0.0019 (16) | 0.0028 (15) |
C21 | 0.0432 (16) | 0.0412 (16) | 0.0462 (19) | 0.0092 (15) | −0.0045 (16) | 0.0011 (14) |
C22 | 0.0341 (17) | 0.081 (2) | 0.076 (2) | 0.0030 (17) | −0.0147 (17) | 0.009 (2) |
C23 | 0.075 (2) | 0.0479 (18) | 0.069 (2) | −0.0007 (18) | 0.002 (2) | −0.0123 (18) |
Geometric parameters (Å, º) top
C1—C15 | 1.388 (3) | C14—C15 | 1.397 (3) |
C1—C2 | 1.388 (3) | C15—H15 | 0.9300 |
C1—C23 | 1.506 (4) | N16—C21 | 1.457 (3) |
C2—C3 | 1.374 (4) | N16—C17 | 1.461 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.507 (3) |
C3—C4 | 1.386 (4) | C17—H17A | 0.9700 |
C3—H3 | 0.9300 | C17—H17B | 0.9700 |
C4—C14 | 1.387 (3) | C18—N19 | 1.459 (3) |
C4—N5 | 1.429 (3) | C18—H18A | 0.9700 |
N5—C6 | 1.415 (3) | C18—H18B | 0.9700 |
N5—H5 | 0.917 (16) | N19—C22 | 1.459 (3) |
C6—N7 | 1.329 (3) | N19—C20 | 1.462 (3) |
C6—C11 | 1.408 (3) | C20—C21 | 1.496 (3) |
N7—C8 | 1.344 (3) | C20—H20A | 0.9700 |
C8—C9 | 1.370 (4) | C20—H20B | 0.9700 |
C8—H8 | 0.9300 | C21—H21A | 0.9700 |
C9—C10 | 1.383 (3) | C21—H21B | 0.9700 |
C9—H9 | 0.9300 | C22—H22A | 0.9600 |
C10—C11 | 1.385 (3) | C22—H22B | 0.9600 |
C10—H10 | 0.9300 | C22—H22C | 0.9600 |
C11—N12 | 1.402 (3) | C23—H23A | 0.9600 |
N12—C13 | 1.284 (3) | C23—H23B | 0.9600 |
C13—N16 | 1.379 (3) | C23—H23C | 0.9600 |
C13—C14 | 1.494 (3) | | |
| | | |
C15—C1—C2 | 117.0 (3) | C13—N16—C17 | 124.2 (2) |
C15—C1—C23 | 121.7 (2) | C21—N16—C17 | 110.7 (2) |
C2—C1—C23 | 121.3 (3) | N16—C17—C18 | 110.3 (2) |
C3—C2—C1 | 121.3 (3) | N16—C17—H17A | 109.6 |
C3—C2—H2 | 119.3 | C18—C17—H17A | 109.6 |
C1—C2—H2 | 119.3 | N16—C17—H17B | 109.6 |
C2—C3—C4 | 120.9 (3) | C18—C17—H17B | 109.6 |
C2—C3—H3 | 119.6 | H17A—C17—H17B | 108.1 |
C4—C3—H3 | 119.6 | N19—C18—C17 | 109.9 (2) |
C3—C4—C14 | 119.6 (2) | N19—C18—H18A | 109.7 |
C3—C4—N5 | 119.9 (2) | C17—C18—H18A | 109.7 |
C14—C4—N5 | 120.5 (3) | N19—C18—H18B | 109.7 |
C6—N5—C4 | 115.4 (2) | C17—C18—H18B | 109.7 |
C6—N5—H5 | 109.7 (18) | H18A—C18—H18B | 108.2 |
C4—N5—H5 | 112.0 (17) | C18—N19—C22 | 110.7 (2) |
N7—C6—C11 | 123.9 (2) | C18—N19—C20 | 109.3 (2) |
N7—C6—N5 | 116.2 (2) | C22—N19—C20 | 111.1 (2) |
C11—C6—N5 | 119.9 (2) | N19—C20—C21 | 110.5 (2) |
C6—N7—C8 | 117.8 (2) | N19—C20—H20A | 109.5 |
N7—C8—C9 | 123.1 (3) | C21—C20—H20A | 109.5 |
N7—C8—H8 | 118.4 | N19—C20—H20B | 109.5 |
C9—C8—H8 | 118.4 | C21—C20—H20B | 109.5 |
C8—C9—C10 | 118.2 (3) | H20A—C20—H20B | 108.1 |
C8—C9—H9 | 120.9 | N16—C21—C20 | 109.6 (2) |
C10—C9—H9 | 120.9 | N16—C21—H21A | 109.7 |
C9—C10—C11 | 120.9 (3) | C20—C21—H21A | 109.7 |
C9—C10—H10 | 119.6 | N16—C21—H21B | 109.7 |
C11—C10—H10 | 119.6 | C20—C21—H21B | 109.7 |
C10—C11—N12 | 117.8 (2) | H21A—C21—H21B | 108.2 |
C10—C11—C6 | 116.0 (2) | N19—C22—H22A | 109.5 |
N12—C11—C6 | 125.5 (2) | N19—C22—H22B | 109.5 |
C13—N12—C11 | 124.0 (2) | H22A—C22—H22B | 109.5 |
N12—C13—N16 | 117.1 (2) | N19—C22—H22C | 109.5 |
N12—C13—C14 | 126.0 (2) | H22A—C22—H22C | 109.5 |
N16—C13—C14 | 116.4 (2) | H22B—C22—H22C | 109.5 |
C4—C14—C15 | 118.3 (2) | C1—C23—H23A | 109.5 |
C4—C14—C13 | 121.5 (2) | C1—C23—H23B | 109.5 |
C15—C14—C13 | 120.1 (2) | H23A—C23—H23B | 109.5 |
C1—C15—C14 | 122.8 (2) | C1—C23—H23C | 109.5 |
C1—C15—H15 | 118.6 | H23A—C23—H23C | 109.5 |
C14—C15—H15 | 118.6 | H23B—C23—H23C | 109.5 |
C13—N16—C21 | 120.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N7i | 0.92 (2) | 2.30 (2) | 3.214 (3) | 175 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |