8-Methyl-6-(4-methyl­piperazin-1-yl)-11H-pyrido­[2,3-b][1,4]­benzodiazepine

The conformation of the title compound, C₁₈H₂₁N₅, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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)-11H-pyrido[2,3-b][1,4]benzodiazepine

Crystal data

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) Å^3	Prismatic, yellow
Z = 8	0.35 × 0.30 × 0.25 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.034P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N7^i	0.92 (2)	2.30 (2)	3.214 (3)	175 (2)

Symmetry code: (i) −x+1, −y, −z+1.