2,3,4,5-Tetra­hydro-r-2,c-4-di­phenyl-1,5-benzo­thia­zepine

The single-crystal X-ray diffraction study of the title mol­ecule, C₂₁H₁₉NS, confirms the twist-boat conformation of the thia­zepine ring. The two phenyl groups are equatorially oriented with respect to the thia­zepine ring.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.131
• Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(5)   -   H(5)              ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST96 (Nardelli, 1983).

2,3,4,5-tetrahydro-r-2,c-4-diphenyl-1,5-benzothiazepine

Crystal data

C21H19NS	F(000) = 672
Mr = 317.43	Dx = 1.231 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.4782 (15) Å	Cell parameters from 1726 reflections
b = 6.0737 (7) Å	θ = 10–28°
c = 21.918 (3) Å	µ = 0.19 mm^−1
β = 107.327 (3)°	T = 150 K
V = 1712.9 (3) Å^3	Needle, colorless
Z = 4	0.44 × 0.09 × 0.08 mm

Data collection

Siemens SMART 1K CCD diffractometer	4168 independent reflections
Radiation source: fine-focus sealed tube	1824 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
ω–2θ scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.922, Tmax = 0.985	k = −8→7
10671 measured reflections	l = −29→23

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0529P)^2] where P = (Fo^2 + 2Fc^2)/3
4168 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. Note that the absorption correction parameters Tmin and Tmax also reflect beam corrections, etc. As a result, the numerical values for Tmin and Tmax may differ from expected values based solely on absorption effects and crystal size.

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48346 (5)	0.01363 (11)	0.21604 (3)	0.0472 (2)
C2	0.54426 (17)	0.1918 (4)	0.16927 (12)	0.0376 (6)
H2	0.5703 (7)	0.329 (4)	0.1953 (7)	0.0536 (19)*
C3	0.46731 (17)	0.2622 (4)	0.10604 (12)	0.0413 (7)
H3A	0.4541 (3)	0.137 (2)	0.0758 (5)	0.0536 (19)*
H3B	0.4980 (5)	0.383 (2)	0.0873 (3)	0.0536 (19)*
C4	0.36355 (17)	0.3399 (4)	0.11473 (11)	0.0382 (6)
H4	0.3261 (9)	0.207 (3)	0.1238 (3)	0.0536 (19)*
N5	0.38407 (17)	0.4882 (4)	0.17049 (10)	0.0415 (6)
H5	0.3539 (17)	0.607 (4)	0.1624 (11)	0.031 (7)*
C6	0.34809 (19)	0.5523 (5)	0.26950 (13)	0.0485 (7)
H6	0.3223 (7)	0.698 (4)	0.2536 (5)	0.0536 (19)*
C7	0.3479 (2)	0.4895 (6)	0.32974 (15)	0.0596 (9)
H7	0.3232 (7)	0.590 (3)	0.3557 (7)	0.0536 (19)*
C8	0.3825 (2)	0.2842 (6)	0.35319 (15)	0.0615 (9)
H8	0.3800 (2)	0.2415 (14)	0.3921 (12)	0.0536 (19)*
C9	0.42121 (19)	0.1450 (5)	0.31596 (13)	0.0512 (8)
H9	0.4458 (7)	0.003 (4)	0.3320 (4)	0.0536 (19)*
C10	0.42529 (17)	0.2063 (4)	0.25539 (12)	0.0380 (6)
C11	0.38459 (17)	0.4111 (4)	0.23052 (12)	0.0379 (6)
C20	0.63783 (18)	0.0677 (4)	0.16231 (12)	0.0413 (7)
C21	0.73709 (18)	0.1488 (5)	0.18881 (12)	0.0434 (7)
H21	0.7467 (3)	0.284 (4)	0.2107 (6)	0.0536 (19)*
C22	0.8226 (2)	0.0324 (5)	0.18339 (13)	0.0516 (8)
H22	0.8903 (19)	0.0890 (17)	0.2018 (5)	0.0536 (19)*
C23	0.8092 (2)	−0.1641 (6)	0.15139 (14)	0.0589 (9)
H23	0.8658 (16)	−0.239 (2)	0.14774 (18)	0.0536 (19)*
C24	0.7115 (2)	−0.2488 (6)	0.12479 (15)	0.0622 (9)
H24	0.7026 (4)	−0.383 (4)	0.1035 (6)	0.0536 (19)*
C25	0.6260 (2)	−0.1312 (5)	0.13005 (14)	0.0575 (8)
H25	0.5550 (18)	−0.1910 (16)	0.1103 (5)	0.0536 (19)*
C30	0.29268 (19)	0.4552 (4)	0.05716 (12)	0.0404 (7)
C31	0.1950 (2)	0.3696 (6)	0.02670 (13)	0.0555 (8)
H31	0.1744 (6)	0.230 (4)	0.0406 (4)	0.0536 (19)*
C32	0.1268 (3)	0.4819 (7)	−0.02313 (14)	0.0711 (10)
H32	0.0644 (18)	0.4260 (18)	−0.0422 (6)	0.0536 (19)*
C33	0.1546 (3)	0.6768 (7)	−0.04321 (16)	0.0742 (11)
H33	0.1104 (14)	0.749 (2)	−0.0746 (10)	0.0536 (19)*
C34	0.2509 (3)	0.7616 (6)	−0.01491 (16)	0.0758 (11)
H34	0.2703 (7)	0.891 (4)	−0.0290 (4)	0.0536 (19)*
C35	0.3183 (2)	0.6508 (5)	0.03482 (14)	0.0608 (9)
H35	0.3881 (18)	0.7146 (17)	0.0553 (6)	0.0536 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0483 (4)	0.0415 (4)	0.0530 (4)	0.0054 (3)	0.0166 (3)	0.0031 (4)
C2	0.0343 (14)	0.0359 (16)	0.0423 (16)	0.0012 (11)	0.0111 (12)	−0.0010 (12)
C3	0.0396 (15)	0.0418 (15)	0.0419 (16)	0.0037 (12)	0.0113 (13)	−0.0010 (13)
C4	0.0345 (14)	0.0373 (15)	0.0395 (15)	−0.0012 (12)	0.0058 (12)	−0.0023 (13)
N5	0.0455 (13)	0.0372 (14)	0.0408 (14)	0.0091 (11)	0.0112 (10)	−0.0019 (12)
C6	0.0382 (15)	0.0592 (19)	0.0454 (17)	0.0047 (13)	0.0083 (13)	−0.0095 (15)
C7	0.0425 (16)	0.089 (3)	0.0483 (19)	0.0101 (17)	0.0147 (13)	−0.013 (2)
C8	0.0453 (18)	0.101 (3)	0.0389 (17)	0.0005 (18)	0.0129 (14)	0.0052 (19)
C9	0.0366 (15)	0.068 (2)	0.0444 (18)	−0.0007 (14)	0.0051 (13)	0.0111 (16)
C10	0.0267 (13)	0.0452 (17)	0.0399 (15)	−0.0014 (12)	0.0067 (11)	0.0005 (13)
C11	0.0290 (13)	0.0450 (16)	0.0387 (15)	−0.0026 (11)	0.0083 (11)	−0.0040 (13)
C20	0.0358 (15)	0.0415 (17)	0.0462 (16)	0.0022 (12)	0.0116 (13)	0.0014 (13)
C21	0.0374 (15)	0.0488 (17)	0.0424 (16)	0.0009 (13)	0.0095 (12)	0.0019 (14)
C22	0.0345 (15)	0.072 (2)	0.0461 (17)	0.0013 (15)	0.0087 (13)	0.0074 (16)
C23	0.0466 (19)	0.075 (2)	0.057 (2)	0.0241 (17)	0.0177 (15)	0.0110 (18)
C24	0.058 (2)	0.0538 (19)	0.073 (2)	0.0125 (16)	0.0178 (17)	−0.0108 (17)
C25	0.0371 (16)	0.0526 (19)	0.078 (2)	0.0017 (14)	0.0099 (15)	−0.0159 (17)
C30	0.0359 (14)	0.0454 (17)	0.0399 (15)	0.0035 (12)	0.0112 (12)	0.0000 (13)
C31	0.0477 (18)	0.079 (2)	0.0402 (17)	−0.0121 (16)	0.0130 (15)	−0.0007 (16)
C32	0.0425 (17)	0.120 (3)	0.0425 (18)	−0.0093 (19)	0.0006 (14)	0.013 (2)
C33	0.064 (2)	0.103 (3)	0.047 (2)	0.026 (2)	0.0030 (18)	0.013 (2)
C34	0.080 (3)	0.062 (2)	0.071 (2)	0.005 (2)	0.002 (2)	0.026 (2)
C35	0.0546 (18)	0.0503 (19)	0.063 (2)	−0.0034 (15)	−0.0052 (16)	0.0099 (17)

Geometric parameters (Å, º)

S1—C10	1.770 (3)	C20—C21	1.381 (3)
S1—C2	1.842 (2)	C20—C25	1.385 (4)
C2—C20	1.515 (3)	C21—C22	1.387 (3)
C2—C3	1.524 (3)	C21—H21	0.94
C2—H2	1.01	C22—C23	1.369 (4)
C3—C4	1.541 (3)	C22—H22	0.95
C3—H3A	0.99	C23—C24	1.372 (4)
C3—H3B	0.99	C23—H23	0.91
C4—N5	1.476 (3)	C24—C25	1.389 (4)
C4—C30	1.509 (3)	C24—H24	0.93
C4—H4	1.00	C25—H25	0.99
N5—C11	1.395 (3)	C30—C35	1.368 (4)
N5—H5	0.82 (2)	C30—C31	1.388 (3)
C6—C7	1.375 (4)	C31—C32	1.380 (4)
C6—C11	1.399 (3)	C31—H31	0.97
C6—H6	0.98	C32—C33	1.354 (4)
C7—C8	1.376 (4)	C32—H32	0.89
C7—H7	0.96	C33—C34	1.362 (4)
C8—C9	1.380 (4)	C33—H33	0.88
C8—H8	0.90	C34—C35	1.370 (4)
C9—C10	1.396 (3)	C34—H34	0.91
C9—H9	0.95	C35—H35	0.99
C10—C11	1.402 (3)
C10—S1—C2	102.58 (12)	N5—C11—C10	123.8 (2)
C20—C2—C3	114.2 (2)	C6—C11—C10	118.3 (2)
C20—C2—S1	106.58 (16)	C21—C20—C25	118.4 (2)
C3—C2—S1	112.07 (17)	C21—C20—C2	120.8 (2)
C20—C2—H2	107.9	C25—C20—C2	120.9 (2)
C3—C2—H2	107.9	C20—C21—C22	120.5 (3)
S1—C2—H2	107.9	C20—C21—H21	119.7
C2—C3—C4	111.7 (2)	C22—C21—H21	119.7
C2—C3—H3A	109.3	C23—C22—C21	120.1 (3)
C4—C3—H3A	109.3	C23—C22—H22	119.9
C2—C3—H3B	109.3	C21—C22—H22	119.9
C4—C3—H3B	109.3	C22—C23—C24	120.5 (3)
H3A—C3—H3B	107.9	C22—C23—H23	119.7
N5—C4—C30	109.0 (2)	C24—C23—H23	119.7
N5—C4—C3	109.64 (19)	C23—C24—C25	119.1 (3)
C30—C4—C3	114.2 (2)	C23—C24—H24	120.4
N5—C4—H4	107.9	C25—C24—H24	120.4
C30—C4—H4	107.9	C20—C25—C24	121.3 (3)
C3—C4—H4	107.9	C20—C25—H25	119.4
C11—N5—C4	121.5 (2)	C24—C25—H25	119.4
C11—N5—H5	111.2 (16)	C35—C30—C31	117.2 (3)
C4—N5—H5	113.5 (16)	C35—C30—C4	122.5 (2)
C7—C6—C11	121.2 (3)	C31—C30—C4	120.1 (2)
C7—C6—H6	119.4	C32—C31—C30	120.5 (3)
C11—C6—H6	119.4	C32—C31—H31	119.7
C6—C7—C8	120.8 (3)	C30—C31—H31	119.7
C6—C7—H7	119.6	C33—C32—C31	120.4 (3)
C8—C7—H7	119.6	C33—C32—H32	119.8
C7—C8—C9	118.7 (3)	C31—C32—H32	119.8
C7—C8—H8	120.7	C32—C33—C34	120.0 (3)
C9—C8—H8	120.7	C32—C33—H33	120.0
C8—C9—C10	121.9 (3)	C34—C33—H33	120.0
C8—C9—H9	119.1	C33—C34—C35	119.5 (3)
C10—C9—H9	119.1	C33—C34—H34	120.2
C9—C10—C11	119.0 (2)	C35—C34—H34	120.2
C9—C10—S1	115.8 (2)	C30—C35—C34	122.2 (3)
C11—C10—S1	125.2 (2)	C30—C35—H35	118.9
N5—C11—C6	117.8 (2)	C34—C35—H35	118.9
C10—S1—C2—C20	151.07 (17)	S1—C2—C20—C21	−116.3 (2)
C10—S1—C2—C3	−83.4 (2)	C3—C2—C20—C25	−61.6 (3)
C20—C2—C3—C4	167.2 (2)	S1—C2—C20—C25	62.7 (3)
S1—C2—C3—C4	45.9 (3)	C25—C20—C21—C22	−0.3 (4)
C2—C3—C4—N5	45.3 (3)	C2—C20—C21—C22	178.7 (2)
C2—C3—C4—C30	168.0 (2)	C20—C21—C22—C23	0.2 (4)
C30—C4—N5—C11	138.0 (2)	C21—C22—C23—C24	−0.4 (4)
C3—C4—N5—C11	−96.3 (3)	C22—C23—C24—C25	0.7 (4)
C11—C6—C7—C8	−0.7 (4)	C21—C20—C25—C24	0.7 (4)
C6—C7—C8—C9	2.3 (4)	C2—C20—C25—C24	−178.4 (3)
C7—C8—C9—C10	−0.5 (4)	C23—C24—C25—C20	−0.9 (5)
C8—C9—C10—C11	−3.0 (4)	N5—C4—C30—C35	58.8 (3)
C8—C9—C10—S1	176.8 (2)	C3—C4—C30—C35	−64.2 (3)
C2—S1—C10—C9	−147.55 (19)	N5—C4—C30—C31	−117.7 (3)
C2—S1—C10—C11	32.2 (2)	C3—C4—C30—C31	119.3 (3)
C4—N5—C11—C6	−145.6 (2)	C35—C30—C31—C32	−1.3 (4)
C4—N5—C11—C10	38.4 (3)	C4—C30—C31—C32	175.4 (2)
C7—C6—C11—N5	−178.9 (2)	C30—C31—C32—C33	0.3 (4)
C7—C6—C11—C10	−2.7 (4)	C31—C32—C33—C34	1.1 (5)
C9—C10—C11—N5	−179.6 (2)	C32—C33—C34—C35	−1.5 (5)
S1—C10—C11—N5	0.7 (3)	C31—C30—C35—C34	0.9 (4)
C9—C10—C11—C6	4.4 (3)	C4—C30—C35—C34	−175.7 (3)
S1—C10—C11—C6	−175.28 (18)	C33—C34—C35—C30	0.5 (5)
C3—C2—C20—C21	119.4 (3)