5H-2,4-Dimeth­yl-6-phen­yl-8,9-dihydro­pyrido[3′,2′:5,6][1,2]thia­zino[3,2-c][1,4]oxazin-5-one 11,11-dioxide

The structure of the title compound, C₁₈H₁₆N₂O₄S, with a new chiral pyrido[3′,2′:5,6][1,2]thia­zino[3,2-c][1,4]oxazine ring system, is described. Both partially saturated thia­zine and oxazine rings adopt diplanar conformations. The mol­ecular packing is influenced by weak C—H...O and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT391_ALERT_3_B Deviating Methyl C16     H-C-H Bond Angle ......      98.00 Deg.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C14    -   H142   ...       0.78 Ang.
PLAT351_ALERT_3_C Long    C-H Bond (0.96A)   C13    -   H132   ...       1.11 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           28.66
           From the CIF: _reflns_number_total               3439
           Count of symmetry unique reflns         2294
           Completeness (_total/calc)            149.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1145
           Fraction of Friedel pairs measured     0.499
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Kuma Diffraction, 2001); cell refinement: CrysAlis RED (Kuma Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Sheldrick, 1989); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

H-2,4-Dimethyl-6-phenyl-8,9-dihydropyrido[3',2':5,6][1,2]thiazino[3,2-c]- [1,4]oxazin-5-one-11,11-dioxide

Crystal data

C18H16N2O4S	F(000) = 372
Mr = 356.39	Dx = 1.401 Mg m^−3
Monoclinic, P21	Melting point = 474–476 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.618 (1) Å	Cell parameters from 4038 reflections
b = 10.280 (2) Å	θ = 1.9–24.5°
c = 10.936 (1) Å	µ = 0.22 mm^−1
β = 99.55 (1)°	T = 293 K
V = 844.6 (2) Å^3	Prism, yellow
Z = 2	0.80 × 0.51 × 0.13 mm

Data collection

Kuma KM-4 diffractometer	3439 independent reflections
Radiation source: fine-focus sealed tube	2962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
ω scans	θmax = 28.7°, θmin = 3.4°
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	h = −10→10
Tmin = 0.890, Tmax = 0.975	k = −9→13
10762 measured reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	Only H-atom coordinates refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.048P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.22 e Å^−3
3439 reflections	Δρmin = −0.31 e Å^−3
275 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.028 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1315 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.05 (6)

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.2757 (0.0022) x - 2.9015 (0.0077) y - 0.7575 (0.0075) z = 2.1928 (0.0029) * 0.0014 (0.0013) C5 * 0.0152 (0.0014) C6 * -0.0173 (0.0013) C7 * 0.0010 (0.0013) N8 * 0.0166 (0.0013) C9 * -0.0169 (0.0012) C10 0.0058 (0.0034) C15 - 0.0923 (0.0039) C16 Rms deviation of fitted atoms = 0.0135

6.7380 (0.0035) x + 4.7084 (0.0084) y - 0.6455 (0.0094) z = 3.0120 (0.0020) A ngle to previous plane (with approximate e.s.d.) = 43.65 (0.05) * -0.0071 (0.0014) C21 * 0.0032 (0.0015) C22 * 0.0023 (0.0016) C23 * -0.0041 (0.0017) C24 * 0.0002 (0.0016) C25 * 0.0054 (0.0014) C26 Rms deviation of fitted atoms = 0.0043

6.4980 (0.0033) x - 4.4996 (0.0048) y - 4.6137 (0.0090) z = 1.6019 (0.0015) A ngle to previous plane (with approximate e.s.d.) = 58.08 (0.05) * 0.1115 (0.0011) C10 * 0.0041 (0.0014) C4 * -0.1296 (0.0010) O4 * -0.0424 (0.0013) C3 * -0.0972 (0.0013) C11 * 0.1535 (0.0011) C21 Rms deviation of fitted atoms = 0.1033

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	0.30652 (7)	−0.06487 (5)	0.37002 (4)	0.04686 (16)
O1S	0.1473 (3)	0.0096 (2)	0.36594 (17)	0.0704 (5)
O2S	0.4185 (2)	−0.0849 (2)	0.48637 (11)	0.0717 (6)
O4	0.15428 (19)	−0.09136 (15)	−0.01273 (11)	0.0494 (4)
O12	0.4559 (2)	0.22874 (15)	0.14683 (12)	0.0496 (4)
N2	0.4347 (2)	−0.00717 (16)	0.27561 (13)	0.0387 (4)
N8	0.2162 (2)	−0.31044 (19)	0.36942 (14)	0.0430 (4)
C3	0.3524 (2)	0.01004 (19)	0.14847 (15)	0.0337 (4)
C4	0.2428 (2)	−0.09977 (18)	0.09110 (15)	0.0336 (4)
C5	0.1772 (2)	−0.34072 (19)	0.11027 (16)	0.0353 (4)
C6	0.1468 (3)	−0.4419 (2)	0.18798 (19)	0.0415 (4)
H61	0.116 (4)	−0.519 (3)	0.163 (2)	0.062*
C7	0.1626 (2)	−0.4245 (2)	0.31608 (17)	0.0422 (5)
C9	0.2484 (2)	−0.21533 (19)	0.29393 (16)	0.0373 (4)
C10	0.2285 (2)	−0.22007 (19)	0.16504 (15)	0.0327 (4)
C11	0.3784 (2)	0.12130 (18)	0.08844 (16)	0.0355 (4)
C13	0.4909 (5)	0.2240 (3)	0.2799 (2)	0.0631 (7)
H131	0.371 (4)	0.234 (4)	0.308 (3)	0.095*
H132	0.575 (4)	0.309 (4)	0.315 (3)	0.095*
C14	0.5626 (3)	0.0956 (2)	0.3228 (2)	0.0540 (6)
H141	0.680 (4)	0.080 (3)	0.284 (3)	0.081*
H142	0.582 (4)	0.081 (3)	0.394 (3)	0.081*
C15	0.1537 (3)	−0.3651 (2)	−0.02745 (19)	0.0464 (5)
H151	0.164 (4)	−0.452 (3)	−0.046 (3)	0.070*
H152	0.246 (4)	−0.319 (3)	−0.068 (3)	0.070*
H153	0.031 (4)	−0.325 (3)	−0.069 (3)	0.070*
C16	0.1181 (4)	−0.5317 (3)	0.3985 (3)	0.0594 (7)
H161	0.223 (4)	−0.571 (4)	0.446 (3)	0.089*
H162	0.047 (4)	−0.582 (4)	0.352 (3)	0.089*
H163	0.071 (4)	−0.496 (4)	0.464 (3)	0.089*
C21	0.3386 (2)	0.14716 (19)	−0.04710 (16)	0.0350 (4)
C22	0.3916 (3)	0.0618 (2)	−0.13270 (18)	0.0419 (4)
H221	0.451 (3)	−0.016 (3)	−0.111 (2)	0.063*
C23	0.3587 (3)	0.0915 (3)	−0.2579 (2)	0.0527 (5)
H231	0.386 (4)	0.038 (3)	−0.322 (3)	0.079*
C24	0.2731 (3)	0.2072 (3)	−0.2976 (2)	0.0569 (6)
H241	0.250 (4)	0.233 (4)	−0.380 (3)	0.085*
C25	0.2223 (3)	0.2924 (3)	−0.2139 (2)	0.0543 (6)
H251	0.162 (4)	0.372 (3)	−0.235 (3)	0.081*
C26	0.2558 (3)	0.2627 (2)	−0.0878 (2)	0.0449 (5)
H216	0.222 (4)	0.319 (3)	−0.031 (3)	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0675 (3)	0.0460 (3)	0.0294 (2)	−0.0055 (3)	0.01473 (18)	−0.0067 (2)
O1S	0.0839 (11)	0.0602 (11)	0.0782 (11)	0.0053 (9)	0.0460 (9)	−0.0125 (9)
O2S	0.1128 (13)	0.0740 (14)	0.0249 (6)	−0.0316 (12)	0.0013 (7)	−0.0032 (8)
O4	0.0599 (8)	0.0454 (9)	0.0361 (6)	−0.0085 (7)	−0.0121 (6)	0.0076 (6)
O12	0.0763 (10)	0.0344 (8)	0.0374 (7)	−0.0117 (7)	0.0073 (6)	−0.0074 (6)
N2	0.0507 (9)	0.0395 (9)	0.0245 (7)	−0.0063 (7)	0.0020 (6)	−0.0049 (6)
N8	0.0466 (9)	0.0495 (11)	0.0329 (8)	−0.0045 (8)	0.0066 (6)	0.0058 (7)
C3	0.0401 (9)	0.0339 (10)	0.0264 (7)	−0.0002 (8)	0.0034 (7)	−0.0027 (7)
C4	0.0358 (8)	0.0341 (10)	0.0302 (7)	0.0008 (7)	0.0037 (6)	−0.0004 (7)
C5	0.0357 (9)	0.0330 (10)	0.0366 (9)	−0.0002 (7)	0.0042 (7)	−0.0012 (7)
C6	0.0430 (10)	0.0358 (11)	0.0446 (10)	−0.0036 (8)	0.0040 (8)	0.0020 (9)
C7	0.0419 (10)	0.0442 (12)	0.0401 (10)	−0.0025 (9)	0.0055 (8)	0.0083 (9)
C9	0.0423 (10)	0.0398 (11)	0.0293 (8)	−0.0012 (8)	0.0044 (7)	−0.0012 (8)
C10	0.0347 (8)	0.0349 (10)	0.0283 (8)	0.0002 (7)	0.0041 (6)	−0.0005 (7)
C11	0.0433 (9)	0.0304 (10)	0.0330 (8)	−0.0006 (8)	0.0072 (7)	−0.0064 (7)
C13	0.102 (2)	0.0459 (14)	0.0389 (11)	−0.0163 (15)	0.0040 (11)	−0.0167 (10)
C14	0.0708 (15)	0.0539 (15)	0.0335 (9)	−0.0186 (12)	−0.0021 (10)	−0.0079 (10)
C15	0.0663 (14)	0.0387 (11)	0.0345 (10)	−0.0072 (10)	0.0092 (9)	−0.0071 (8)
C16	0.0700 (15)	0.0543 (17)	0.0534 (13)	−0.0118 (12)	0.0091 (11)	0.0154 (11)
C21	0.0393 (9)	0.0324 (9)	0.0332 (8)	−0.0051 (7)	0.0057 (7)	0.0000 (7)
C22	0.0510 (11)	0.0380 (11)	0.0370 (9)	0.0005 (9)	0.0086 (8)	−0.0038 (8)
C23	0.0649 (13)	0.0565 (15)	0.0371 (10)	−0.0088 (11)	0.0102 (9)	−0.0049 (10)
C24	0.0641 (13)	0.0652 (17)	0.0393 (11)	−0.0156 (12)	0.0019 (10)	0.0164 (11)
C25	0.0561 (13)	0.0472 (14)	0.0580 (13)	−0.0025 (11)	0.0049 (10)	0.0191 (11)
C26	0.0529 (11)	0.0339 (11)	0.0495 (11)	−0.0009 (9)	0.0129 (9)	0.0017 (9)

Geometric parameters (Å, º)

S1—O2S	1.4244 (15)	C13—C14	1.475 (4)
S1—O1S	1.429 (2)	C13—H131	1.02 (3)
S1—N2	1.6450 (17)	C13—H132	1.11 (4)
S1—C9	1.777 (2)	C14—H141	1.06 (3)
O4—C4	1.2236 (19)	C14—H142	0.79 (3)
O12—C11	1.361 (2)	C15—H151	0.92 (3)
O12—C13	1.437 (3)	C15—H152	1.01 (3)
N2—C3	1.438 (2)	C15—H153	1.05 (3)
N2—C14	1.471 (3)	C16—H161	0.97 (3)
N8—C9	1.329 (3)	C16—H162	0.85 (4)
N8—C7	1.343 (3)	C16—H163	0.93 (4)
C3—C11	1.350 (3)	C21—C26	1.383 (3)
C3—C4	1.480 (2)	C21—C22	1.391 (3)
C4—C10	1.491 (3)	C22—C23	1.384 (3)
C5—C6	1.386 (3)	C22—H221	0.93 (3)
C5—C10	1.404 (3)	C23—C24	1.390 (4)
C5—C15	1.508 (3)	C23—H231	0.94 (3)
C6—C7	1.397 (3)	C24—C25	1.368 (4)
C6—H61	0.86 (3)	C24—H241	0.93 (3)
C7—C16	1.498 (3)	C25—C26	1.394 (3)
C9—C10	1.393 (2)	C25—H251	0.94 (3)
C11—C21	1.487 (2)	C26—H216	0.92 (3)
O2S—S1—O1S	119.00 (11)	C14—C13—H132	115.8 (18)
O2S—S1—N2	106.43 (9)	H131—C13—H132	108 (3)
O1S—S1—N2	112.11 (10)	N2—C14—C13	110.02 (19)
O2S—S1—C9	111.00 (11)	N2—C14—H141	108.0 (18)
O1S—S1—C9	107.91 (11)	C13—C14—H141	107.4 (19)
N2—S1—C9	98.50 (8)	N2—C14—H142	102 (2)
C11—O12—C13	116.16 (17)	C13—C14—H142	119 (3)
C3—N2—C14	114.06 (16)	H141—C14—H142	110 (3)
C3—N2—S1	116.23 (12)	C5—C15—H151	112.1 (18)
C14—N2—S1	117.82 (13)	C5—C15—H152	112.7 (15)
C9—N8—C7	116.54 (16)	H151—C15—H152	106 (3)
C11—C3—N2	119.93 (16)	C5—C15—H153	108.5 (16)
C11—C3—C4	123.92 (15)	H151—C15—H153	113 (2)
N2—C3—C4	116.15 (15)	H152—C15—H153	105 (2)
O4—C4—C3	121.64 (16)	C7—C16—H161	113 (2)
O4—C4—C10	118.90 (16)	C7—C16—H162	106 (2)
C3—C4—C10	119.29 (14)	H161—C16—H162	117 (3)
C6—C5—C10	117.63 (17)	C7—C16—H163	109 (2)
C6—C5—C15	118.90 (19)	H161—C16—H163	98 (3)
C10—C5—C15	123.47 (17)	H162—C16—H163	114 (3)
C5—C6—C7	121.6 (2)	C26—C21—C22	119.54 (18)
C5—C6—H61	124.3 (18)	C26—C21—C11	118.74 (17)
C7—C6—H61	114.1 (18)	C22—C21—C11	121.62 (17)
N8—C7—C6	121.09 (18)	C23—C22—C21	120.1 (2)
N8—C7—C16	117.64 (19)	C23—C22—H221	116.5 (17)
C6—C7—C16	121.3 (2)	C21—C22—H221	123.5 (17)
N8—C9—C10	127.06 (19)	C22—C23—C24	119.7 (2)
N8—C9—S1	114.01 (13)	C22—C23—H231	125 (2)
C10—C9—S1	118.74 (14)	C24—C23—H231	115 (2)
C9—C10—C5	115.99 (17)	C25—C24—C23	120.6 (2)
C9—C10—C4	120.94 (17)	C25—C24—H241	116 (2)
C5—C10—C4	122.77 (15)	C23—C24—H241	123 (2)
C3—C11—O12	123.16 (16)	C24—C25—C26	119.7 (2)
C3—C11—C21	127.92 (16)	C24—C25—H251	124.9 (18)
O12—C11—C21	108.87 (16)	C26—C25—H251	115.4 (18)
O12—C13—C14	110.4 (2)	C21—C26—C25	120.3 (2)
O12—C13—H131	106.1 (17)	C21—C26—H216	119.3 (17)
C14—C13—H131	107 (2)	C25—C26—H216	120.4 (17)
O12—C13—H132	108.5 (18)
O2S—S1—N2—C3	174.79 (15)	S1—C9—C10—C4	−4.3 (2)
O1S—S1—N2—C3	−53.51 (17)	C6—C5—C10—C9	1.6 (2)
C9—S1—N2—C3	59.84 (15)	C15—C5—C10—C9	−178.39 (18)
O2S—S1—N2—C14	−44.5 (2)	C6—C5—C10—C4	−172.06 (16)
O1S—S1—N2—C14	87.20 (18)	C15—C5—C10—C4	7.9 (3)
C9—S1—N2—C14	−159.45 (16)	O4—C4—C10—C9	−148.27 (17)
C14—N2—C3—C11	−8.1 (3)	C3—C4—C10—C9	27.1 (2)
S1—N2—C3—C11	134.06 (16)	O4—C4—C10—C5	25.1 (3)
C14—N2—C3—C4	171.48 (18)	C3—C4—C10—C5	−159.50 (16)
S1—N2—C3—C4	−46.4 (2)	N2—C3—C11—O12	−10.9 (3)
C11—C3—C4—O4	−6.9 (3)	C4—C3—C11—O12	169.54 (17)
N2—C3—C4—O4	173.54 (16)	N2—C3—C11—C21	165.93 (17)
C11—C3—C4—C10	177.87 (16)	C4—C3—C11—C21	−13.6 (3)
N2—C3—C4—C10	−1.7 (2)	C13—O12—C11—C3	−7.2 (3)
C10—C5—C6—C7	1.4 (3)	C13—O12—C11—C21	175.4 (2)
C15—C5—C6—C7	−178.59 (19)	C11—O12—C13—C14	42.3 (3)
C9—N8—C7—C6	1.7 (3)	C3—N2—C14—C13	42.2 (3)
C9—N8—C7—C16	−177.5 (2)	S1—N2—C14—C13	−99.3 (2)
C5—C6—C7—N8	−3.2 (3)	O12—C13—C14—N2	−59.2 (3)
C5—C6—C7—C16	176.0 (2)	C3—C11—C21—C26	135.4 (2)
C7—N8—C9—C10	1.7 (3)	O12—C11—C21—C26	−47.3 (2)
C7—N8—C9—S1	176.65 (13)	C3—C11—C21—C22	−48.3 (3)
O2S—S1—C9—N8	39.05 (17)	O12—C11—C21—C22	128.94 (19)
O1S—S1—C9—N8	−92.99 (16)	C26—C21—C22—C23	−1.1 (3)
N2—S1—C9—N8	150.38 (14)	C11—C21—C22—C23	−177.38 (18)
O2S—S1—C9—C10	−145.54 (14)	C21—C22—C23—C24	0.2 (3)
O1S—S1—C9—C10	82.42 (16)	C22—C23—C24—C25	0.5 (4)
N2—S1—C9—C10	−34.22 (16)	C23—C24—C25—C26	−0.3 (4)
N8—C9—C10—C5	−3.4 (3)	C22—C21—C26—C25	1.3 (3)
S1—C9—C10—C5	−178.13 (13)	C11—C21—C26—C25	177.69 (18)
N8—C9—C10—C4	170.45 (17)	C24—C25—C26—C21	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H61···O4^i	0.86 (3)	2.52 (3)	3.136 (3)	129 (2)
C13—H132···O2S^ii	1.11 (4)	2.42 (3)	3.207 (3)	126 (2)
C23—H231···O2S^iii	0.94 (3)	2.49 (3)	3.426 (3)	171 (3)

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