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The title compound, C17H20N4S, generic name olanzapine, is an antipsychotic agent. The mol­ecule consists of three fused rings (benzene, diazepine and thio­phene) and an N-methyl­piperazine substituent. The boat conformation of the central 1,5-diazepine ring defines the overall shape of the mol­ecule. Two butterfly-like mol­ecules form centrosymmetric dimers stabilized by C—H...π interactions between their cavities. The dimers are connected by intermolecular N—H...N, C—H...N and C—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302806X/wn6201sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302806X/wn6201Isup2.hkl
Contains datablock I

CCDC reference: 232150

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.096
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT480_ALERT_4_A Long H...A H-Bond Reported H191 .. C11 = 3.44 Ang.
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT480_ALERT_4_B Long H...A H-Bond Reported H182 .. N4 = 3.04 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H101 .. S1 = 3.26 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H161 .. C13 = 3.24 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H161 .. C14 = 3.19 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H171 .. C3 = 3.34 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H171 .. C5 = 3.17 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H171 .. C6 = 3.39 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H191 .. C12 = 3.28 Ang.
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H181 .. N4 = 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H182 .. C8 = 2.80 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H182 .. C9 = 2.79 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C16 .. C13 = 4.19 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C16 .. C14 = 4.18 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C17 .. C3 = 4.34 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C17 .. C5 = 4.03 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C17 .. C6 = 4.16 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C19 .. C11 = 4.35 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C19 .. C12 = 4.21 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C18 .. N4 = 92.00 Deg.
1 ALERT level A = In general: serious problem 9 ALERT level B = Potentially serious problem 11 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 0 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 20 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 top
Crystal data top
C17H20N4SF(000) = 664
Mr = 312.43Dx = 1.296 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 30 reflections
a = 10.388 (3) Åθ = 6.4–24.4°
b = 14.839 (4) ŵ = 1.80 mm1
c = 10.567 (3) ÅT = 293 K
β = 100.64 (3)°Prism, yellow
V = 1600.9 (8) Å30.34 × 0.22 × 0.2 mm
Z = 4
Data collection top
Kuma KM4 four-circle
diffractometer
Rint = 0.027
Radiation source: fine-focus sealed tubeθmax = 80.2°, θmin = 4.3°
Graphite monochromatorh = 813
ω–2θ scansk = 180
3564 measured reflectionsl = 138
3471 independent reflections3 standard reflections every 100 reflections
2896 reflections with I > 2σ(I) intensity decay: 1.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033All H-atom parameters refined
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.054P)2 + 0.2828P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3471 reflectionsΔρmax = 0.22 e Å3
280 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (5)
Special details top

Experimental. Table X-ray powder diffraction patterns: interplanar spacing - d (Å); relative intensity - I/Imax × 100.

this paper form II (Bunnell et al., 1996) h k l d Int d Int

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)

- 6.8917 (0.0062) x + 11.0673 (0.0086) y + 0.6712 (0.0051) z = 6.4237 (0.0090)

* 0.0065 (0.0006) S1 * -0.0038 (0.0007) C5 * -0.0014 (0.0009) C6 * 0.0078 (0.0009) C8 * -0.0090 (0.0008) C9 - 0.0161 (0.0030) C10

Rms deviation of fitted atoms = 0.0063

1.8880 (0.0064) x + 14.1427 (0.0079) y - 2.8690 (0.0067) z = 11.2231 (0.0073)

Angle to previous plane (with approximate e.s.d.) = 52.79 (0.05)

* -0.0035 (0.0009) C2 * 0.0045 (0.0010) C3 * 0.0012 (0.0011) C11 * -0.0078 (0.0012) C12 * 0.0087 (0.0012) C13 * -0.0031 (0.0011) C14

Rms deviation of fitted atoms = 0.0055

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
xyzUiso*/Ueq
S10.52188 (3)0.89878 (3)0.11882 (3)0.04620 (13)
N10.38761 (10)0.83476 (8)0.51107 (10)0.0377 (2)
C20.26956 (12)0.84261 (9)0.42038 (12)0.0354 (3)
C30.25160 (12)0.81895 (9)0.28916 (12)0.0372 (3)
N40.36065 (11)0.79246 (9)0.23547 (11)0.0434 (3)
C50.46354 (12)0.85365 (9)0.24849 (12)0.0371 (3)
C60.52871 (12)0.88755 (9)0.36237 (12)0.0367 (3)
C70.50121 (12)0.85724 (9)0.48737 (12)0.0358 (3)
C80.62748 (13)0.95098 (9)0.34418 (13)0.0416 (3)
C90.63778 (14)0.96345 (10)0.21947 (14)0.0445 (3)
C100.7301 (2)1.02353 (15)0.16574 (18)0.0604 (4)
C110.12725 (14)0.81999 (11)0.21359 (14)0.0462 (3)
C120.01889 (14)0.84425 (12)0.26501 (15)0.0515 (4)
C130.03459 (14)0.86920 (12)0.39256 (16)0.0507 (3)
C140.15850 (13)0.86737 (10)0.46919 (13)0.0429 (3)
N20.60758 (10)0.85945 (8)0.58712 (10)0.0393 (3)
C150.73349 (13)0.82038 (11)0.57117 (14)0.0426 (3)
C160.84432 (13)0.86637 (11)0.66141 (14)0.0457 (3)
N30.82546 (11)0.85776 (9)0.79376 (11)0.0449 (3)
C170.70196 (14)0.90021 (11)0.80667 (13)0.0446 (3)
C180.58908 (13)0.85389 (10)0.72025 (12)0.0410 (3)
C190.93548 (19)0.8966 (2)0.8828 (2)0.0711 (6)
H4N0.3468 (18)0.7616 (14)0.1659 (19)0.064 (5)*
H80.6796 (16)0.9829 (11)0.4135 (16)0.048 (4)*
H1010.695 (3)1.080 (2)0.145 (3)0.135 (12)*
H1020.759 (2)0.9964 (18)0.094 (3)0.099 (8)*
H1030.809 (2)1.0347 (17)0.229 (2)0.092 (7)*
H110.1180 (17)0.8019 (12)0.1252 (18)0.058 (5)*
H120.0670 (18)0.8428 (13)0.2126 (18)0.061 (5)*
H130.0413 (19)0.8877 (13)0.4294 (19)0.065 (5)*
H140.1711 (16)0.8851 (12)0.5595 (17)0.050 (5)*
H1510.7343 (16)0.7581 (13)0.5913 (16)0.050 (4)*
H1520.7465 (17)0.8269 (12)0.4837 (17)0.054 (5)*
H1610.8486 (17)0.9310 (12)0.6373 (17)0.051 (5)*
H1620.9268 (17)0.8350 (12)0.6532 (17)0.055 (5)*
H1710.7026 (16)0.9661 (13)0.7842 (17)0.056 (5)*
H1720.6911 (18)0.8942 (12)0.9007 (19)0.058 (5)*
H1810.5883 (16)0.7899 (12)0.7497 (16)0.052 (5)*
H1820.5018 (17)0.8860 (11)0.7232 (16)0.048 (4)*
H1910.947 (3)0.959 (2)0.865 (3)0.112 (10)*
H1920.921 (2)0.8921 (15)0.970 (2)0.078 (7)*
H1931.020 (2)0.8668 (15)0.876 (2)0.079 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0460 (2)0.0603 (2)0.03218 (18)0.00217 (14)0.00678 (13)0.00146 (13)
N10.0340 (5)0.0447 (6)0.0323 (5)0.0000 (4)0.0005 (4)0.0024 (4)
C20.0322 (6)0.0388 (6)0.0340 (6)0.0014 (5)0.0026 (5)0.0026 (5)
C30.0349 (6)0.0386 (6)0.0365 (6)0.0008 (5)0.0026 (5)0.0018 (5)
N40.0375 (6)0.0517 (7)0.0399 (6)0.0011 (5)0.0041 (4)0.0154 (5)
C50.0347 (6)0.0421 (6)0.0334 (6)0.0047 (5)0.0034 (5)0.0038 (5)
C60.0341 (6)0.0422 (6)0.0330 (6)0.0013 (5)0.0037 (5)0.0018 (5)
C70.0349 (5)0.0390 (6)0.0318 (6)0.0019 (5)0.0017 (5)0.0015 (5)
C80.0409 (7)0.0445 (7)0.0382 (6)0.0034 (5)0.0048 (5)0.0019 (5)
C90.0431 (7)0.0498 (8)0.0411 (7)0.0014 (6)0.0088 (5)0.0017 (6)
C100.0603 (10)0.0720 (12)0.0514 (9)0.0117 (9)0.0167 (8)0.0077 (8)
C110.0400 (7)0.0565 (8)0.0385 (7)0.0026 (6)0.0019 (5)0.0032 (6)
C120.0323 (6)0.0674 (10)0.0506 (8)0.0015 (6)0.0033 (6)0.0009 (7)
C130.0327 (6)0.0677 (10)0.0523 (8)0.0009 (6)0.0093 (6)0.0008 (7)
C140.0359 (6)0.0544 (8)0.0386 (7)0.0042 (6)0.0076 (5)0.0006 (6)
N20.0306 (5)0.0549 (7)0.0310 (5)0.0030 (4)0.0015 (4)0.0019 (4)
C150.0342 (6)0.0536 (8)0.0389 (7)0.0064 (5)0.0034 (5)0.0016 (6)
C160.0325 (6)0.0609 (9)0.0423 (7)0.0013 (6)0.0032 (5)0.0064 (6)
N30.0343 (5)0.0598 (7)0.0371 (6)0.0032 (5)0.0028 (4)0.0040 (5)
C170.0423 (7)0.0550 (9)0.0343 (6)0.0023 (6)0.0010 (5)0.0034 (6)
C180.0346 (6)0.0553 (8)0.0318 (6)0.0016 (6)0.0030 (5)0.0006 (5)
C190.0464 (9)0.1092 (18)0.0506 (9)0.0140 (10)0.0093 (7)0.0054 (10)
Geometric parameters (Å, º) top
S1—C51.7321 (14)C12—H120.960 (19)
S1—C91.7403 (16)C13—C141.389 (2)
N1—C71.2945 (17)C13—H130.98 (2)
N1—C21.4148 (16)C14—H140.975 (17)
C2—C141.3970 (18)N2—C181.4569 (16)
C2—C31.4089 (17)N2—C151.4686 (17)
C3—C111.3877 (18)C15—C161.515 (2)
C3—N41.4132 (17)C15—H1510.948 (19)
N4—C51.3897 (18)C15—H1520.963 (18)
N4—H4N0.86 (2)C16—N31.4532 (18)
C5—C61.3633 (17)C16—H1610.996 (18)
C6—C81.4313 (19)C16—H1620.992 (18)
C6—C71.4723 (17)N3—C171.4581 (19)
C7—N21.3794 (16)N3—C191.458 (2)
C8—C91.3544 (19)C17—C181.5119 (19)
C8—H80.953 (17)C17—H1711.006 (19)
C9—C101.496 (2)C17—H1721.024 (19)
C10—H1010.92 (3)C18—H1811.000 (18)
C10—H1020.96 (3)C18—H1821.029 (17)
C10—H1030.97 (3)C19—H1910.96 (3)
C11—C121.385 (2)C19—H1920.97 (2)
C11—H110.960 (19)C19—H1931.00 (2)
C12—C131.378 (2)
C5—S1—C991.91 (7)C14—C13—H13120.0 (11)
C7—N1—C2123.70 (11)C13—C14—C2121.98 (13)
C14—C2—C3117.42 (12)C13—C14—H14120.5 (10)
C14—C2—N1116.30 (11)C2—C14—H14117.5 (10)
C3—C2—N1125.93 (12)C7—N2—C18120.44 (11)
C11—C3—C2120.24 (13)C7—N2—C15120.51 (11)
C11—C3—N4120.13 (12)C18—N2—C15111.56 (11)
C2—C3—N4119.61 (11)N2—C15—C16109.84 (12)
C5—N4—C3115.93 (11)N2—C15—H151109.3 (10)
C5—N4—H4N116.0 (13)C16—C15—H151108.9 (10)
C3—N4—H4N118.3 (12)N2—C15—H152110.9 (11)
C6—C5—N4125.17 (12)C16—C15—H152109.5 (11)
C6—C5—S1111.49 (10)H151—C15—H152108.4 (15)
N4—C5—S1123.32 (10)N3—C16—C15110.14 (12)
C5—C6—C8112.06 (12)N3—C16—H161110.6 (10)
C5—C6—C7122.15 (12)C15—C16—H161109.7 (10)
C8—C6—C7125.73 (12)N3—C16—H162108.3 (10)
N1—C7—N2119.24 (11)C15—C16—H162107.6 (10)
N1—C7—C6125.95 (11)H161—C16—H162110.5 (14)
N2—C7—C6114.68 (11)C16—N3—C17109.23 (11)
C9—C8—C6114.07 (13)C16—N3—C19110.96 (13)
C9—C8—H8123.0 (10)C17—N3—C19111.54 (15)
C6—C8—H8122.9 (10)N3—C17—C18110.17 (12)
C8—C9—C10128.47 (15)N3—C17—H171110.7 (10)
C8—C9—S1110.45 (11)C18—C17—H171109.7 (10)
C10—C9—S1121.08 (12)N3—C17—H172108.1 (10)
C9—C10—H101112 (2)C18—C17—H172109.5 (11)
C9—C10—H102111.7 (15)H171—C17—H172108.7 (14)
H101—C10—H102111 (2)N2—C18—C17109.37 (11)
C9—C10—H103110.8 (14)N2—C18—H181111.4 (10)
H101—C10—H103105 (2)C17—C18—H181107.1 (10)
H102—C10—H103105.6 (19)N2—C18—H182106.1 (9)
C12—C11—C3120.98 (14)C17—C18—H182111.2 (9)
C12—C11—H11120.8 (11)H181—C18—H182111.8 (13)
C3—C11—H11118.2 (11)N3—C19—H191111.3 (17)
C13—C12—C11119.71 (13)N3—C19—H192110.5 (13)
C13—C12—H12120.0 (11)H191—C19—H192108 (2)
C11—C12—H12120.3 (11)N3—C19—H193111.8 (13)
C12—C13—C14119.64 (14)H191—C19—H193106 (2)
C12—C13—H13120.3 (11)H192—C19—H193109.4 (18)
C7—N1—C2—C14143.86 (14)C6—C8—C9—S11.53 (16)
C7—N1—C2—C343.1 (2)C5—S1—C9—C81.31 (12)
C14—C2—C3—C110.5 (2)C5—S1—C9—C10179.63 (14)
N1—C2—C3—C11172.45 (13)C2—C3—C11—C120.1 (2)
C14—C2—C3—N4179.32 (12)N4—C3—C11—C12178.88 (14)
N1—C2—C3—N46.3 (2)C3—C11—C12—C131.1 (3)
C11—C3—N4—C5125.12 (14)C11—C12—C13—C141.8 (3)
C2—C3—N4—C556.10 (17)C12—C13—C14—C21.4 (2)
C3—N4—C5—C656.60 (18)C3—C2—C14—C130.2 (2)
C3—N4—C5—S1121.57 (12)N1—C2—C14—C13173.86 (14)
C9—S1—C5—C60.77 (11)N1—C7—N2—C1811.82 (19)
C9—S1—C5—N4179.16 (12)C6—C7—N2—C18164.25 (12)
N4—C5—C6—C8178.41 (12)N1—C7—N2—C15135.43 (14)
S1—C5—C6—C80.05 (15)C6—C7—N2—C1548.50 (17)
N4—C5—C6—C74.2 (2)C7—N2—C15—C16153.89 (12)
S1—C5—C6—C7177.49 (10)C18—N2—C15—C1656.21 (16)
C2—N1—C7—N2170.68 (12)N2—C15—C16—N357.56 (16)
C2—N1—C7—C64.9 (2)C15—C16—N3—C1760.28 (16)
C5—C6—C7—N135.4 (2)C15—C16—N3—C19176.36 (16)
C8—C6—C7—N1147.51 (14)C16—N3—C17—C1861.16 (16)
C5—C6—C7—N2148.83 (13)C19—N3—C17—C18175.82 (14)
C8—C6—C7—N228.25 (19)C7—N2—C18—C17153.32 (13)
C5—C6—C8—C90.98 (18)C15—N2—C18—C1756.76 (16)
C7—C6—C8—C9176.35 (13)N3—C17—C18—N259.05 (16)
C6—C8—C9—C10179.50 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···N1i0.86 (2)2.27 (2)3.084 (2)159
C18—H181···N4ii1.00 (2)2.64 (2)3.243 (2)119
C18—H182···N4ii1.03 (2)3.04 (2)3.243 (2)92
C10—H101···S1iii0.92 (3)3.26 (4)3.783 (2)118
C16—H161···C13iv1.00 (2)3.24 (2)4.194 (2)160
C16—H161···C14iv1.00 (2)3.19 (2)4.183 (2)174
C17—H171···C3iv1.01 (2)3.34 (2)4.337 (2)172
C17—H171···C5iv1.01 (2)3.17 (2)4.033 (2)145
C17—H171···C6iv1.01 (2)3.39 (2)4.156 (2)134
C18—H182···C8iv1.03 (2)2.80 (2)3.653 (2)141
C18—H182···C9iv1.03 (2)2.79 (2)3.723 (2)151
C18—H181···C5ii1.00 (2)2.49 (2)3.379 (2)148
C19—H191···C11iv0.96 (3)3.44 (3)4.348 (2)160
C19—H191···C12iv0.96 (3)3.28 (3)4.210 (2)167
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2; (iii) x+1, y+2, z; (iv) x+1, y+2, z+1.
 

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