Olazipinium nicotinate

The crystal structure of the title compound, C₁₇H₂₁N₄S⁺·C₆H₄NO₂⁻, [systematic name: 1-methyl-4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-yl)hexa­hydro­pyrazin-1-ium nicotinate] is reported. The central seven-membered heterocycle is in a boat conformation, while the piperazine ring displays a chair conformation with its methyl group oriented equatorially. The coulombic interaction between olanzapinium and nicotinate ions is supplemented by intra- and inter­molecular N—H...O hydrogen bonds, forming infinite chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.141
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C22    -   C23     ..       6.21 su
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         N5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

1-methyl-4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4- yl)hexahydropyrazin-1-ium nicotinate

Crystal data

C17H21N4S^+·C6H4NO2^−	Z = 2
Mr = 435.54	F(000) = 460
Triclinic, P1	Dx = 1.301 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2565 (10) Å	Cell parameters from 1483 reflections
b = 11.2224 (12) Å	θ = 2.2–21.2°
c = 12.0629 (13) Å	µ = 0.18 mm^−1
α = 63.164 (2)°	T = 273 K
β = 87.485 (2)°	Needle, pale yellow
γ = 83.735 (2)°	0.23 × 0.12 × 0.09 mm
V = 1111.4 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −10→10
8110 measured reflections	k = −13→13
3894 independent reflections	l = −14→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.338P] where P = (Fo^2 + 2Fc^2)/3
3894 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.21 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
S1	0.59536 (8)	0.24922 (8)	0.40971 (7)	0.0450 (3)
N1	0.2341 (2)	0.4088 (2)	0.1008 (2)	0.0355 (6)
N2	0.3996 (2)	0.3091 (2)	0.0135 (2)	0.0361 (6)
N3	0.4853 (3)	0.2493 (3)	−0.1872 (2)	0.0402 (6)
H3N	0.417 (3)	0.182 (3)	−0.178 (3)	0.058 (9)*
N4	0.2996 (3)	0.2773 (3)	0.3677 (2)	0.0420 (7)
H4N	0.293 (3)	0.244 (3)	0.443 (3)	0.029 (8)*
N5	−0.0937 (4)	−0.0773 (4)	0.8549 (4)	0.0990 (13)
C2	0.1899 (3)	0.4651 (3)	0.1817 (3)	0.0348 (7)
C3	0.2153 (3)	0.4037 (3)	0.3109 (3)	0.0370 (7)
C5	0.4409 (3)	0.2794 (3)	0.3209 (2)	0.0326 (7)
C6	0.4739 (3)	0.3157 (3)	0.1998 (2)	0.0309 (6)
C7	0.3603 (3)	0.3456 (3)	0.1067 (2)	0.0309 (6)
C8	0.6275 (3)	0.3206 (3)	0.1787 (3)	0.0361 (7)
H8	0.6686	0.3444	0.1007	0.043*
C9	0.7071 (3)	0.2877 (3)	0.2811 (3)	0.0389 (7)
C10	0.8684 (3)	0.2870 (4)	0.2919 (3)	0.0556 (9)
H10A	0.9129	0.3068	0.2129	0.083*
H10B	0.9080	0.2001	0.3526	0.083*
H10C	0.8873	0.3536	0.3172	0.083*
C11	0.1548 (3)	0.4658 (3)	0.3813 (3)	0.0485 (8)
H11	0.1719	0.4250	0.4665	0.058*
C12	0.0698 (3)	0.5868 (4)	0.3273 (3)	0.0541 (9)
H12	0.0293	0.6264	0.3761	0.065*
C13	0.0452 (3)	0.6487 (3)	0.2010 (3)	0.0507 (8)
H13	−0.0099	0.7315	0.1637	0.061*
C14	0.1027 (3)	0.5873 (3)	0.1300 (3)	0.0419 (7)
H14	0.0828	0.6285	0.0452	0.050*
C15	0.4882 (3)	0.1845 (3)	0.0371 (3)	0.0384 (7)
H15A	0.4259	0.1137	0.0563	0.046*
H15B	0.5513	0.1586	0.1080	0.046*
C16	0.5780 (3)	0.2023 (3)	−0.0746 (3)	0.0424 (8)
H16A	0.6466	0.2672	−0.0887	0.051*
H16B	0.6330	0.1177	−0.0593	0.051*
C17	0.3870 (3)	0.3715 (3)	−0.2055 (3)	0.0430 (8)
H17A	0.3214	0.3953	−0.2745	0.052*
H17B	0.4444	0.4460	−0.2259	0.052*
C18	0.3002 (3)	0.3476 (3)	−0.0901 (2)	0.0392 (7)
H18A	0.2390	0.4286	−0.1027	0.047*
H18B	0.2382	0.2768	−0.0721	0.047*
C19	0.5742 (4)	0.2733 (4)	−0.2993 (3)	0.0647 (10)
H19A	0.5113	0.3011	−0.3697	0.097*
H19B	0.6328	0.1921	−0.2865	0.097*
H19C	0.6360	0.3424	−0.3143	0.097*
O1	0.2962 (2)	0.0798 (2)	0.83969 (18)	0.0513 (6)
O2	0.2842 (3)	0.1911 (3)	0.6352 (2)	0.0734 (8)
C20	0.0985 (3)	0.0536 (3)	0.7389 (3)	0.0384 (7)
C21	0.0265 (4)	0.0805 (4)	0.6313 (3)	0.0564 (9)
H21	0.0660	0.1344	0.5549	0.068*
C22	−0.1005 (4)	0.0299 (4)	0.6347 (4)	0.0634 (10)
H22	−0.1482	0.0484	0.5617	0.076*
C23	−0.1560 (4)	−0.0472 (5)	0.7451 (5)	0.0826 (13)
H23	−0.2429	−0.0823	0.7464	0.099*
C24	0.0345 (4)	−0.0269 (4)	0.8485 (3)	0.0658 (10)
H24	0.0818	−0.0481	0.9224	0.079*
C25	0.2379 (3)	0.1118 (3)	0.7362 (3)	0.0389 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0424 (5)	0.0602 (5)	0.0305 (4)	−0.0003 (4)	−0.0061 (3)	−0.0192 (4)
N1	0.0336 (14)	0.0405 (14)	0.0328 (13)	−0.0025 (11)	0.0012 (10)	−0.0172 (11)
N2	0.0391 (14)	0.0419 (14)	0.0312 (13)	0.0070 (11)	−0.0074 (10)	−0.0216 (11)
N3	0.0460 (15)	0.0469 (15)	0.0373 (14)	−0.0121 (13)	0.0057 (12)	−0.0263 (12)
N4	0.0415 (15)	0.0510 (17)	0.0273 (15)	−0.0091 (12)	0.0067 (12)	−0.0118 (13)
N5	0.096 (3)	0.112 (3)	0.093 (3)	−0.062 (3)	0.033 (2)	−0.042 (3)
C2	0.0263 (15)	0.0451 (18)	0.0363 (16)	−0.0060 (13)	0.0051 (12)	−0.0211 (14)
C3	0.0290 (15)	0.0470 (18)	0.0357 (17)	−0.0108 (13)	0.0074 (13)	−0.0182 (15)
C5	0.0340 (16)	0.0347 (16)	0.0286 (15)	−0.0041 (12)	0.0008 (12)	−0.0137 (13)
C6	0.0309 (15)	0.0329 (15)	0.0291 (15)	−0.0031 (12)	0.0021 (12)	−0.0142 (13)
C7	0.0342 (16)	0.0319 (15)	0.0257 (14)	−0.0055 (13)	0.0025 (12)	−0.0119 (12)
C8	0.0374 (17)	0.0394 (17)	0.0342 (16)	−0.0031 (13)	0.0031 (13)	−0.0193 (14)
C9	0.0336 (16)	0.0453 (18)	0.0393 (17)	0.0011 (13)	−0.0029 (13)	−0.0210 (15)
C10	0.0375 (19)	0.071 (2)	0.058 (2)	0.0010 (16)	−0.0084 (16)	−0.0291 (19)
C11	0.0398 (18)	0.073 (2)	0.0432 (19)	−0.0126 (17)	0.0113 (15)	−0.0351 (18)
C12	0.0416 (19)	0.074 (2)	0.065 (2)	−0.0051 (18)	0.0126 (17)	−0.049 (2)
C13	0.0373 (18)	0.055 (2)	0.066 (2)	0.0009 (15)	0.0044 (16)	−0.0340 (19)
C14	0.0317 (16)	0.0500 (19)	0.0435 (18)	−0.0025 (14)	−0.0001 (14)	−0.0209 (16)
C15	0.0443 (18)	0.0379 (17)	0.0363 (17)	0.0027 (14)	−0.0069 (14)	−0.0203 (14)
C16	0.0400 (18)	0.0478 (19)	0.0496 (19)	−0.0004 (14)	−0.0042 (15)	−0.0313 (16)
C17	0.058 (2)	0.0409 (18)	0.0305 (16)	−0.0007 (15)	−0.0066 (14)	−0.0163 (14)
C18	0.0418 (18)	0.0445 (18)	0.0341 (16)	0.0027 (14)	−0.0072 (13)	−0.0211 (14)
C19	0.065 (2)	0.090 (3)	0.053 (2)	−0.021 (2)	0.0233 (18)	−0.044 (2)
O1	0.0657 (15)	0.0473 (13)	0.0374 (12)	−0.0137 (11)	−0.0109 (11)	−0.0133 (10)
O2	0.0767 (17)	0.102 (2)	0.0333 (13)	−0.0479 (16)	0.0054 (12)	−0.0149 (13)
C20	0.0457 (18)	0.0351 (17)	0.0362 (17)	−0.0033 (14)	0.0013 (14)	−0.0178 (14)
C21	0.053 (2)	0.067 (2)	0.047 (2)	−0.0154 (18)	−0.0005 (17)	−0.0219 (18)
C22	0.048 (2)	0.081 (3)	0.069 (3)	−0.010 (2)	−0.0118 (19)	−0.040 (2)
C23	0.057 (3)	0.089 (3)	0.123 (4)	−0.027 (2)	0.009 (3)	−0.063 (3)
C24	0.080 (3)	0.071 (3)	0.046 (2)	−0.031 (2)	0.0079 (19)	−0.0220 (19)
C25	0.0456 (18)	0.0385 (17)	0.0340 (17)	−0.0031 (14)	−0.0017 (14)	−0.0175 (14)

Geometric parameters (Å, º)

S1—C5	1.734 (3)	C12—C13	1.377 (4)
S1—C9	1.736 (3)	C12—H12	0.9300
N1—C7	1.285 (3)	C13—C14	1.380 (4)
N1—C2	1.409 (3)	C13—H13	0.9300
N2—C7	1.382 (3)	C14—H14	0.9300
N2—C15	1.456 (3)	C15—C16	1.496 (4)
N2—C18	1.456 (3)	C15—H15A	0.9700
N3—C19	1.483 (4)	C15—H15B	0.9700
N3—C16	1.489 (4)	C16—H16A	0.9700
N3—C17	1.493 (4)	C16—H16B	0.9700
N3—H3N	1.00 (3)	C17—C18	1.506 (4)
N4—C5	1.400 (3)	C17—H17A	0.9700
N4—C3	1.421 (4)	C17—H17B	0.9700
N4—H4N	0.81 (3)	C18—H18A	0.9700
N5—C23	1.349 (5)	C18—H18B	0.9700
N5—C24	1.354 (5)	C19—H19A	0.9600
C2—C14	1.396 (4)	C19—H19B	0.9600
C2—C3	1.409 (4)	C19—H19C	0.9600
C3—C11	1.389 (4)	O1—C25	1.261 (3)
C5—C6	1.358 (4)	O2—C25	1.233 (3)
C6—C8	1.435 (4)	C20—C24	1.373 (4)
C6—C7	1.473 (4)	C20—C21	1.378 (4)
C8—C9	1.347 (4)	C20—C25	1.501 (4)
C8—H8	0.9300	C21—C22	1.351 (5)
C9—C10	1.504 (4)	C21—H21	0.9300
C10—H10A	0.9600	C22—C23	1.336 (5)
C10—H10B	0.9600	C22—H22	0.9300
C10—H10C	0.9600	C23—H23	0.9300
C11—C12	1.378 (4)	C24—H24	0.9300
C11—H11	0.9300
C5—S1—C9	91.83 (13)	C13—C14—C2	122.0 (3)
C7—N1—C2	123.1 (2)	C13—C14—H14	119.0
C7—N2—C15	122.5 (2)	C2—C14—H14	119.0
C7—N2—C18	119.4 (2)	N2—C15—C16	110.1 (2)
C15—N2—C18	110.6 (2)	N2—C15—H15A	109.6
C19—N3—C16	111.5 (2)	C16—C15—H15A	109.6
C19—N3—C17	111.2 (2)	N2—C15—H15B	109.6
C16—N3—C17	110.9 (2)	C16—C15—H15B	109.6
C19—N3—H3N	107.5 (17)	H15A—C15—H15B	108.2
C16—N3—H3N	111.4 (17)	N3—C16—C15	111.3 (2)
C17—N3—H3N	104.1 (17)	N3—C16—H16A	109.4
C5—N4—C3	113.3 (2)	C15—C16—H16A	109.4
C5—N4—H4N	115.6 (19)	N3—C16—H16B	109.4
C3—N4—H4N	111.3 (19)	C15—C16—H16B	109.4
C23—N5—C24	115.9 (3)	H16A—C16—H16B	108.0
C14—C2—N1	116.4 (2)	N3—C17—C18	110.9 (2)
C14—C2—C3	117.7 (3)	N3—C17—H17A	109.5
N1—C2—C3	125.7 (3)	C18—C17—H17A	109.5
C11—C3—C2	119.6 (3)	N3—C17—H17B	109.5
C11—C3—N4	120.9 (3)	C18—C17—H17B	109.5
C2—C3—N4	119.4 (3)	H17A—C17—H17B	108.1
C6—C5—N4	124.7 (2)	N2—C18—C17	109.1 (2)
C6—C5—S1	111.7 (2)	N2—C18—H18A	109.9
N4—C5—S1	123.4 (2)	C17—C18—H18A	109.9
C5—C6—C8	111.6 (2)	N2—C18—H18B	109.9
C5—C6—C7	121.5 (2)	C17—C18—H18B	109.9
C8—C6—C7	126.9 (2)	H18A—C18—H18B	108.3
N1—C7—N2	118.4 (2)	N3—C19—H19A	109.5
N1—C7—C6	126.0 (2)	N3—C19—H19B	109.5
N2—C7—C6	115.4 (2)	H19A—C19—H19B	109.5
C9—C8—C6	114.5 (3)	N3—C19—H19C	109.5
C9—C8—H8	122.7	H19A—C19—H19C	109.5
C6—C8—H8	122.7	H19B—C19—H19C	109.5
C8—C9—C10	128.6 (3)	C24—C20—C21	116.4 (3)
C8—C9—S1	110.4 (2)	C24—C20—C25	121.9 (3)
C10—C9—S1	120.9 (2)	C21—C20—C25	121.7 (3)
C9—C10—H10A	109.5	C22—C21—C20	121.2 (3)
C9—C10—H10B	109.5	C22—C21—H21	119.4
H10A—C10—H10B	109.5	C20—C21—H21	119.4
C9—C10—H10C	109.5	C23—C22—C21	118.7 (4)
H10A—C10—H10C	109.5	C23—C22—H22	120.6
H10B—C10—H10C	109.5	C21—C22—H22	120.6
C12—C11—C3	121.3 (3)	C22—C23—N5	124.0 (4)
C12—C11—H11	119.4	C22—C23—H23	118.0
C3—C11—H11	119.4	N5—C23—H23	118.0
C13—C12—C11	119.8 (3)	N5—C24—C20	123.7 (3)
C13—C12—H12	120.1	N5—C24—H24	118.2
C11—C12—H12	120.1	C20—C24—H24	118.2
C12—C13—C14	119.6 (3)	O2—C25—O1	124.5 (3)
C12—C13—H13	120.2	O2—C25—C20	118.7 (3)
C14—C13—H13	120.2	O1—C25—C20	116.8 (3)
C7—N1—C2—C14	143.1 (3)	C5—S1—C9—C10	177.4 (3)
C7—N1—C2—C3	−42.8 (4)	C2—C3—C11—C12	0.1 (4)
C14—C2—C3—C11	−0.5 (4)	N4—C3—C11—C12	−178.3 (3)
N1—C2—C3—C11	−174.5 (3)	C3—C11—C12—C13	−0.7 (5)
C14—C2—C3—N4	178.0 (2)	C11—C12—C13—C14	1.7 (5)
N1—C2—C3—N4	4.0 (4)	C12—C13—C14—C2	−2.1 (5)
C5—N4—C3—C11	−121.8 (3)	N1—C2—C14—C13	176.0 (3)
C5—N4—C3—C2	59.7 (3)	C3—C2—C14—C13	1.5 (4)
C3—N4—C5—C6	−58.2 (4)	C7—N2—C15—C16	−149.3 (2)
C3—N4—C5—S1	116.2 (3)	C18—N2—C15—C16	61.3 (3)
C9—S1—C5—C6	0.5 (2)	C19—N3—C16—C15	177.3 (3)
C9—S1—C5—N4	−174.4 (2)	C17—N3—C16—C15	52.8 (3)
N4—C5—C6—C8	174.2 (2)	N2—C15—C16—N3	−56.3 (3)
S1—C5—C6—C8	−0.7 (3)	C19—N3—C17—C18	−178.4 (2)
N4—C5—C6—C7	−5.5 (4)	C16—N3—C17—C18	−53.7 (3)
S1—C5—C6—C7	179.6 (2)	C7—N2—C18—C17	147.6 (2)
C2—N1—C7—N2	−171.9 (2)	C15—N2—C18—C17	−61.9 (3)
C2—N1—C7—C6	3.4 (4)	N3—C17—C18—N2	57.9 (3)
C15—N2—C7—N1	−144.5 (3)	C24—C20—C21—C22	0.2 (5)
C18—N2—C7—N1	2.3 (4)	C25—C20—C21—C22	−178.6 (3)
C15—N2—C7—C6	39.8 (4)	C20—C21—C22—C23	0.1 (6)
C18—N2—C7—C6	−173.4 (2)	C21—C22—C23—N5	0.7 (7)
C5—C6—C7—N1	39.0 (4)	C24—N5—C23—C22	−1.7 (7)
C8—C6—C7—N1	−140.7 (3)	C23—N5—C24—C20	2.0 (6)
C5—C6—C7—N2	−145.6 (3)	C21—C20—C24—N5	−1.3 (5)
C8—C6—C7—N2	34.7 (4)	C25—C20—C24—N5	177.5 (3)
C5—C6—C8—C9	0.6 (4)	C24—C20—C25—O2	−174.8 (3)
C7—C6—C8—C9	−179.7 (3)	C21—C20—C25—O2	4.0 (5)
C6—C8—C9—C10	−177.6 (3)	C24—C20—C25—O1	2.1 (4)
C6—C8—C9—S1	−0.1 (3)	C21—C20—C25—O1	−179.2 (3)
C5—S1—C9—C8	−0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1^i	1.00 (3)	1.63 (3)	2.628 (3)	175 (3)
N3—H3N···O2^i	1.00 (3)	2.57 (3)	3.219 (3)	122 (2)
N4—H4N···O2	0.81 (3)	2.12 (3)	2.922 (3)	170 (3)
C19—H19A···O2^i	0.96	2.54	3.173 (4)	124
C17—H17B···Cg1^ii	0.97	2.72	3.55	144

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