2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno­[2,3-b][1,5]­benzodiazepine methanol solvate

Wawrzycka-Gorczyca, I.; Mazur, L.; Koziol, A.E.

doi:10.1107/S1600536803028071

2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine methanol solvate

I. Wawrzycka-Gorczyca, L. Mazur and A. E. Koziol

The title compound, C₁₇H₂₀N₄S·CH₄O, is an olanzapine 1:1 methanol solvate. A pair of olanzapine molecules forms a centrosymmetric dimer with intermolecular C—H

π interactions. Intermolecular host–host N—H

N hydrogen bonds were not found. The guest molecule is linked to host molecules through O—H

N, N—H

O and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028071/wn6202sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028071/wn6202Isup2.hkl Contains datablock I

CCDC reference: 232151

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.063
wR factor = 0.276
Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         29 Perc.

Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H103   ..  N4       =       3.10 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H162   ..  C13      =       3.34 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H162   ..  C14      =       3.19 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H171   ..  C5       =       3.18 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H171   ..  C6       =       3.34 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H171   ..  C8       =       3.34 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H193   ..  C11      =       3.23 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H193   ..  C12      =       3.31 Ang.

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.276
PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max  Low .......       0.94
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1M    -   H1O      =       1.01 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H12    ..  H102     =       2.13 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H101   ..  N4       =       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O1M      =       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H182   ..  C8       =       3.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H182   ..  C9       =       2.93 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16    ..  C13      =       4.21 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16    ..  C14      =       4.14 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C17    ..  C5       =       4.10 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C17    ..  C6       =       4.18 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C17    ..  C8       =       3.94 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  C11      =       4.18 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  C12      =       4.18 Ang.

   1 ALERT level A = In general: serious problem
   8 ALERT level B = Potentially serious problem
  17 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  19 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM4 Software (Kuma Diffraction, 1991); cell refinement: KM4 Software; data reduction: KM4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine methanol solvate top

Crystal data top

C₁₇H₂₀N₄S·CH₄O	F(000) = 736
M_r = 344.47	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 43 reflections
a = 10.207 (3) Å	θ = 8–16°
b = 12.440 (4) Å	µ = 1.68 mm⁻¹
c = 14.278 (5) Å	T = 293 K
β = 92.60 (3)°	Prism, yellow
V = 1811.1 (10) Å³	0.26 × 0.19 × 0.15 mm
Z = 4

Data collection top

Kuma KM-4 four-circle diffractometer	R_int = 0.080
Radiation source: fine-focus sealed tube	θ_max = 80.2°, θ_min = 4.3°
Graphite monochromator	h = −13→0
ω–2θ scans	k = 0→15
4123 measured reflections	l = −18→18
3913 independent reflections	3 standard reflections every 100 reflections
1140 reflections with I > 2σ(I)	intensity decay: 8.7%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom, difmap
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.276	w = 1/[σ²(F_o²) + (0.1344P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3913 reflections	Δρ_max = 0.49 e Å⁻³
218 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (9)

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.

Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.5109 (0.0227) x + 7.8273 (0.0243) y - 6.7472 (0.0273) z = 9.4458 (0.0348)

* -0.0058 (0.0026) S1 * 0.0110 (0.0032) C5 * -0.0121 (0.0037) C6 * 0.0068 (0.0038) C8 * 0.0001 (0.0033) C9 0.0547 (0.0102) C10

Rms deviation of fitted atoms = 0.0084

- 2.6804 (0.0257) x + 10.8708 (0.0164) y - 5.6655 (0.0344) z = 2.8682 (0.0510)

Angle to previous plane (with approximate e.s.d.) = 55.66 (0.19)

* -0.0018 (0.0043) C2 * -0.0024 (0.0044) C3 * 0.0046 (0.0046) C11 * -0.0028 (0.0050) C12 * -0.0015 (0.0050) C13 * 0.0039 (0.0046) C14

Rms deviation of fitted atoms = 0.0030

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

	x	y	z	U_iso*/U_eq
S1	0.94296 (16)	1.09953 (13)	0.78639 (10)	0.0594 (5)
N1	1.1495 (5)	0.8479 (4)	0.6008 (3)	0.0536 (12)
C2	1.2514 (6)	0.9075 (5)	0.6434 (4)	0.0557 (14)
C3	1.2522 (5)	0.9545 (5)	0.7333 (4)	0.0518 (14)
N4	1.1368 (5)	0.9490 (4)	0.7862 (3)	0.0553 (12)
H4N	1.1618	0.9596	0.8511	0.066*
C5	1.0258 (5)	0.9941 (5)	0.7415 (4)	0.0493 (13)
C6	0.9725 (6)	0.9621 (4)	0.6563 (4)	0.0500 (14)
C7	1.0263 (5)	0.8724 (4)	0.6047 (3)	0.0479 (13)
C8	0.8665 (5)	1.0280 (5)	0.6277 (4)	0.0513 (14)
H8	0.8204	1.0191	0.5706	0.062*
C9	0.8369 (5)	1.1052 (5)	0.6897 (4)	0.0557 (14)
C10	0.7344 (6)	1.1913 (5)	0.6826 (4)	0.0657 (17)
H101	0.7381	1.2335	0.7390	0.079*
H102	0.6493	1.1589	0.6744	0.079*
H103	0.7500	1.2368	0.6299	0.079*
C11	1.3643 (7)	1.0027 (6)	0.7714 (5)	0.0687 (18)
H11	1.3638	1.0343	0.8305	0.082*
C12	1.4765 (7)	1.0039 (6)	0.7218 (5)	0.075 (2)
H12	1.5520	1.0357	0.7482	0.090*
C13	1.4794 (7)	0.9591 (6)	0.6343 (5)	0.078 (2)
H13	1.5555	0.9601	0.6008	0.094*
C14	1.3673 (6)	0.9129 (5)	0.5977 (4)	0.0627 (17)
H14	1.3692	0.8830	0.5381	0.075*
N2	0.9384 (5)	0.8142 (4)	0.5488 (3)	0.0576 (13)
C15	0.8091 (5)	0.7867 (5)	0.5789 (4)	0.0547 (15)
H151	0.7793	0.8414	0.6214	0.066*
H152	0.8128	0.7187	0.6122	0.066*
C16	0.7148 (6)	0.7782 (5)	0.4963 (4)	0.0651 (17)
H161	0.6294	0.7569	0.5169	0.078*
H162	0.7058	0.8477	0.4659	0.078*
N3	0.7607 (5)	0.6993 (4)	0.4295 (3)	0.0594 (13)
C17	0.8893 (6)	0.7297 (5)	0.4002 (4)	0.0616 (16)
H171	0.8838	0.7986	0.3685	0.074*
H172	0.9197	0.6769	0.3562	0.074*
C18	0.9857 (6)	0.7372 (5)	0.4827 (4)	0.0590 (16)
H181	0.9957	0.6674	0.5125	0.071*
H182	1.0706	0.7596	0.4619	0.071*
C19	0.6698 (8)	0.6909 (7)	0.3480 (5)	0.094 (2)
H191	0.5850	0.6696	0.3680	0.112*
H192	0.7014	0.6382	0.3055	0.112*
H193	0.6630	0.7593	0.3171	0.112*
O1M	0.7815 (7)	0.5004 (4)	0.5188 (3)	0.110 (2)
H1O	0.7625	0.5731	0.4898	0.132*
C1M	0.6888 (9)	0.4216 (9)	0.4735 (6)	0.121 (3)
H1M	0.7282	0.3515	0.4746	0.146*
H2M	0.6691	0.4427	0.4097	0.146*
H3M	0.6094	0.4198	0.5070	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0668 (9)	0.0577 (10)	0.0537 (8)	−0.0026 (8)	0.0019 (7)	−0.0105 (7)
N1	0.060 (3)	0.047 (3)	0.053 (3)	0.002 (2)	−0.005 (2)	−0.007 (2)
C2	0.059 (3)	0.054 (4)	0.053 (3)	0.003 (3)	−0.005 (3)	0.006 (3)
C3	0.045 (3)	0.051 (3)	0.058 (3)	−0.004 (3)	−0.010 (3)	0.002 (3)
N4	0.058 (3)	0.062 (3)	0.045 (3)	−0.002 (2)	−0.007 (2)	0.003 (2)
C5	0.059 (3)	0.044 (3)	0.044 (3)	0.000 (3)	−0.003 (2)	0.004 (3)
C6	0.059 (3)	0.048 (3)	0.042 (3)	0.001 (3)	−0.005 (2)	−0.002 (2)
C7	0.059 (3)	0.042 (3)	0.043 (3)	0.002 (3)	0.002 (2)	−0.003 (2)
C8	0.050 (3)	0.054 (4)	0.049 (3)	−0.002 (3)	−0.002 (2)	−0.010 (3)
C9	0.052 (3)	0.057 (4)	0.059 (3)	−0.005 (3)	0.002 (3)	−0.005 (3)
C10	0.067 (4)	0.059 (4)	0.071 (4)	0.002 (3)	0.002 (3)	−0.006 (3)
C11	0.077 (4)	0.067 (4)	0.061 (4)	−0.009 (4)	−0.015 (3)	0.004 (3)
C12	0.062 (4)	0.080 (5)	0.081 (5)	−0.015 (4)	−0.014 (3)	0.025 (4)
C13	0.054 (4)	0.093 (6)	0.086 (5)	−0.002 (4)	−0.002 (3)	0.018 (4)
C14	0.050 (3)	0.078 (5)	0.061 (4)	0.007 (3)	0.004 (3)	0.004 (3)
N2	0.055 (3)	0.059 (3)	0.059 (3)	−0.003 (2)	0.006 (2)	−0.015 (2)
C15	0.056 (3)	0.053 (4)	0.055 (3)	−0.003 (3)	−0.001 (3)	−0.007 (3)
C16	0.059 (4)	0.060 (4)	0.076 (4)	−0.001 (3)	−0.005 (3)	−0.005 (3)
N3	0.063 (3)	0.063 (3)	0.051 (3)	0.000 (3)	−0.009 (2)	−0.010 (2)
C17	0.076 (4)	0.053 (4)	0.055 (3)	0.007 (3)	−0.006 (3)	−0.008 (3)
C18	0.056 (4)	0.065 (4)	0.056 (3)	0.003 (3)	0.002 (3)	−0.012 (3)
C19	0.098 (6)	0.098 (6)	0.081 (5)	−0.013 (5)	−0.031 (4)	−0.009 (4)
O1M	0.187 (6)	0.071 (3)	0.069 (3)	−0.022 (4)	−0.036 (3)	0.010 (3)
C1M	0.119 (8)	0.147 (9)	0.097 (6)	−0.01	−0.005 (6)	0.031 (6)

Geometric parameters (Å, º) top

S1—C5	1.701 (6)	C13—H13	0.9300
S1—C9	1.717 (6)	C14—H14	0.9300
N1—C7	1.298 (7)	N2—C18	1.442 (7)
N1—C2	1.394 (7)	N2—C15	1.448 (7)
C2—C14	1.378 (8)	C15—C16	1.492 (7)
C2—C3	1.410 (8)	C15—H151	0.9700
C3—C11	1.382 (8)	C15—H152	0.9700
C3—N4	1.428 (7)	C16—N3	1.460 (7)
N4—C5	1.392 (7)	C16—H161	0.9700
N4—H4N	0.9590	C16—H162	0.9700
C5—C6	1.369 (7)	N3—C17	1.445 (8)
C6—C8	1.403 (7)	N3—C19	1.458 (7)
C6—C7	1.458 (8)	C17—C18	1.504 (7)
C7—N2	1.380 (7)	C17—H171	0.9700
C8—C9	1.350 (8)	C17—H172	0.9700
C8—H8	0.9300	C18—H181	0.9700
C9—C10	1.498 (8)	C18—H182	0.9700
C10—H101	0.9600	C19—H191	0.9600
C10—H102	0.9600	C19—H192	0.9600
C10—H103	0.9600	C19—H193	0.9600
C11—C12	1.374 (10)	O1M—C1M	1.489 (10)
C11—H11	0.9300	O1M—H1O	1.0108
C12—C13	1.370 (9)	C1M—H1M	0.9600
C12—H12	0.9300	C1M—H2M	0.9600
C13—C14	1.363 (9)	C1M—H3M	0.9600

C5—S1—C9	92.0 (3)	C7—N2—C18	119.9 (5)
C7—N1—C2	124.2 (5)	C7—N2—C15	122.0 (4)
C14—C2—N1	117.3 (6)	C18—N2—C15	112.0 (5)
C14—C2—C3	116.2 (6)	N2—C15—C16	110.2 (5)
N1—C2—C3	126.2 (5)	N2—C15—H151	109.6
C11—C3—C2	120.6 (6)	C16—C15—H151	109.6
C11—C3—N4	120.0 (5)	N2—C15—H152	109.6
C2—C3—N4	119.4 (5)	C16—C15—H152	109.6
C5—N4—C3	114.3 (4)	H151—C15—H152	108.1
C5—N4—H4N	124.2	N3—C16—C15	110.5 (5)
C3—N4—H4N	108.3	N3—C16—H161	109.6
C6—C5—N4	124.9 (5)	C15—C16—H161	109.6
C6—C5—S1	112.0 (4)	N3—C16—H162	109.6
N4—C5—S1	123.1 (4)	C15—C16—H162	109.6
C5—C6—C8	111.1 (5)	H161—C16—H162	108.1
C5—C6—C7	121.9 (5)	C17—N3—C19	110.0 (5)
C8—C6—C7	127.0 (5)	C17—N3—C16	109.6 (5)
N1—C7—N2	117.3 (5)	C19—N3—C16	110.9 (5)
N1—C7—C6	126.1 (5)	N3—C17—C18	111.1 (5)
N2—C7—C6	116.4 (5)	N3—C17—H171	109.4
C9—C8—C6	114.7 (5)	C18—C17—H171	109.4
C9—C8—H8	122.7	N3—C17—H172	109.4
C6—C8—H8	122.7	C18—C17—H172	109.4
C8—C9—C10	129.9 (5)	H171—C17—H172	108.0
C8—C9—S1	110.2 (4)	N2—C18—C17	109.1 (5)
C10—C9—S1	119.8 (4)	N2—C18—H181	109.9
C9—C10—H101	109.5	C17—C18—H181	109.9
C9—C10—H102	109.5	N2—C18—H182	109.9
H101—C10—H102	109.5	C17—C18—H182	109.9
C9—C10—H103	109.5	H181—C18—H182	108.3
H101—C10—H103	109.5	N3—C19—H191	109.5
H102—C10—H103	109.5	N3—C19—H192	109.5
C12—C11—C3	119.8 (6)	H191—C19—H192	109.5
C12—C11—H11	120.1	N3—C19—H193	109.5
C3—C11—H11	120.1	H191—C19—H193	109.5
C13—C12—C11	121.3 (6)	H192—C19—H193	109.5
C13—C12—H12	119.4	C1M—O1M—H1O	107.7
C11—C12—H12	119.4	O1M—C1M—H1M	109.5
C14—C13—C12	117.9 (7)	O1M—C1M—H2M	109.5
C14—C13—H13	121.0	H1M—C1M—H2M	109.5
C12—C13—H13	121.0	O1M—C1M—H3M	109.5
C13—C14—C2	124.3 (6)	H1M—C1M—H3M	109.5
C13—C14—H14	117.9	H2M—C1M—H3M	109.5
C2—C14—H14	117.9

C7—N1—C2—C14	−145.4 (6)	C6—C8—C9—S1	0.9 (7)
C7—N1—C2—C3	41.2 (9)	C5—S1—C9—C8	0.3 (5)
C14—C2—C3—C11	0.1 (9)	C5—S1—C9—C10	−177.1 (5)
N1—C2—C3—C11	173.5 (5)	C2—C3—C11—C12	−0.7 (10)
C14—C2—C3—N4	−177.9 (5)	N4—C3—C11—C12	177.3 (6)
N1—C2—C3—N4	−4.6 (9)	C3—C11—C12—C13	0.8 (10)
C11—C3—N4—C5	124.1 (6)	C11—C12—C13—C14	−0.2 (11)
C2—C3—N4—C5	−57.9 (7)	C12—C13—C14—C2	−0.5 (11)
C3—N4—C5—C6	58.8 (8)	N1—C2—C14—C13	−173.5 (6)
C3—N4—C5—S1	−119.2 (5)	C3—C2—C14—C13	0.5 (9)
C9—S1—C5—C6	−1.5 (5)	N1—C7—N2—C18	−5.9 (8)
C9—S1—C5—N4	176.8 (5)	C6—C7—N2—C18	168.9 (5)
N4—C5—C6—C8	−176.0 (5)	N1—C7—N2—C15	144.3 (5)
S1—C5—C6—C8	2.2 (6)	C6—C7—N2—C15	−40.9 (7)
N4—C5—C6—C7	2.3 (9)	C7—N2—C15—C16	150.3 (5)
S1—C5—C6—C7	−179.5 (4)	C18—N2—C15—C16	−57.3 (6)
C2—N1—C7—N2	171.4 (5)	N2—C15—C16—N3	56.9 (7)
C2—N1—C7—C6	−2.8 (9)	C15—C16—N3—C17	−58.0 (7)
C5—C6—C7—N1	−36.4 (9)	C15—C16—N3—C19	−179.6 (6)
C8—C6—C7—N1	141.7 (6)	C19—N3—C17—C18	−179.1 (6)
C5—C6—C7—N2	149.3 (5)	C16—N3—C17—C18	58.7 (6)
C8—C6—C7—N2	−32.6 (9)	C7—N2—C18—C17	−149.9 (5)
C5—C6—C8—C9	−2.0 (8)	C15—N2—C18—C17	57.0 (6)
C7—C6—C8—C9	179.8 (6)	N3—C17—C18—N2	−57.9 (7)
C6—C8—C9—C10	178.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1O···N3	1.01	1.79	2.788 (7)	169
N4—H4N···O1Mⁱ	0.96	1.99	2.941 (6)	173
C10—H101···N4ⁱ	0.96	3.00	3.486 (8)	113
C10—H103···N4ⁱ	0.96	3.10	3.486 (8)	106
C11—H11···O1Mⁱ	0.93	2.70	3.405 (9)	133
C10—H101···C2ⁱ	0.96	2.74	3.660 (8)	161
C10—H101···C3ⁱ	0.96	2.78	3.488 (8)	131
C16—H162···C13ⁱⁱ	0.97	3.34	4.213 (9)	151
C16—H162···C14ⁱⁱ	0.97	3.19	4.144 (9)	167
C17—H171···C5ⁱⁱ	0.97	3.18	4.101 (9)	159
C17—H171···C6ⁱⁱ	0.97	3.34	4.177 (8)	145
C17—H171···C8ⁱⁱ	0.97	3.34	3.944 (9)	122
C18—H182···C8ⁱⁱ	0.97	3.02	3.676 (9)	126
C18—H182···C9ⁱⁱ	0.97	2.93	3.687 (9)	136
C19—H193···C11ⁱⁱ	0.96	3.23	4.184 (11)	176
C19—H193···C12ⁱⁱ	0.96	3.31	4.184 (11)	153

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+2, −y+2, −z+1.

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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno­[2,3-b][1,5]­benzodiazepine methanol solvate

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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine methanol solvate