[1-(Benzyl­sulfon­yl)-3-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­quinoxalin-2-yl](4-bromo­phen­yl)methanone 2-methyl­propanol hemisolvate

In the title compound, C₂₈H₂₂BrN₃O₅S·0.5C₄H₁₀O, the tetra­hydro­pyrazine ring adopts a distorted half-chair conformation. The bromo­benzaldehyde substituent has an axial orientation, while the 4-nitro­phenyl group is in an equatorial position. The benzene rings of these substituents are not parallel, but are partially involved in intra­molecular π–π stacking. In the crystal structure, the methanone mol­ecules form a centrosymmetric dimer via inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.055
• wR factor = 0.152
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        4000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.08 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C22     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  O1      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O4      ..       2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25    ..  O4      ..       2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O2      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  O2      ..       2.74 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[1-(Benzylsulfonyl)-3-(4-nitrophenyl)-1,2,3,4-tetrahydroquinoxalin-2-yl](4- bromophenyl)methanone 2-methylpropanol hemisolvate

Crystal data

C28H22BrN3O5S·0.5C4H10O	Z = 2
Mr = 629.52	F(000) = 646
Triclinic, P1	Dx = 1.436 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.768 (4) Å	Cell parameters from 24 reflections
b = 11.002 (5) Å	θ = 10–11°
c = 15.026 (9) Å	µ = 1.53 mm^−1
α = 73.84 (4)°	T = 293 K
β = 71.68 (4)°	Prism, yellow
γ = 77.04 (4)°	0.40 × 0.20 × 0.20 mm
V = 1455.9 (13) Å^3

Data collection

Siemens P3 diffractometer	3085 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.1°, θmin = 2.0°
ω–2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.549, Tmax = 0.737	l = −16→17
5272 measured reflections	2 standard reflections every 98 reflections
4970 independent reflections	intensity decay: 3.2%

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.1035P)^2] where P = (Fo^2 + 2Fc^2)/3
4970 reflections	(Δ/σ)max = 0.003
390 parameters	Δρmax = 0.91 e Å^−3
44 restraints	Δρmin = −0.72 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.

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	Occ. (<1)
Br1	1.18018 (6)	−0.09466 (6)	0.63691 (4)	0.0746 (3)
S1	0.37976 (11)	0.25463 (9)	0.45965 (7)	0.0348 (3)
N1	0.3433 (4)	0.2403 (3)	0.5770 (2)	0.0378 (8)
N2	0.3096 (4)	0.2274 (3)	0.7706 (3)	0.0527 (10)
H2N	0.3269	0.2358	0.8211	0.063*
N3	0.7469 (5)	−0.2465 (5)	0.9399 (3)	0.0658 (12)
O1	0.4846 (3)	0.1456 (2)	0.43786 (19)	0.0406 (7)
O2	0.2461 (3)	0.2745 (3)	0.4350 (2)	0.0477 (7)
O3	0.5694 (4)	0.3301 (3)	0.5921 (3)	0.0587 (9)
O4	0.7956 (5)	−0.3498 (4)	0.9166 (3)	0.0927 (13)
O5	0.7776 (5)	−0.2164 (4)	1.0028 (3)	0.0894 (13)
C1	0.1556 (6)	0.4356 (5)	0.5777 (4)	0.0596 (13)
H1	0.1637	0.4441	0.5130	0.071*
C2	0.0580 (6)	0.5241 (5)	0.6263 (4)	0.0705 (16)
H2	0.0026	0.5918	0.5941	0.085*
C3	0.0443 (6)	0.5108 (5)	0.7212 (4)	0.0692 (15)
H3	−0.0209	0.5696	0.7543	0.083*
C4	0.1249 (6)	0.4126 (5)	0.7676 (4)	0.0625 (13)
H4	0.1131	0.4047	0.8327	0.075*
C5	0.2244 (5)	0.3230 (4)	0.7220 (3)	0.0478 (10)
C6	0.2411 (4)	0.3349 (4)	0.6235 (3)	0.0416 (10)
C7	0.3700 (5)	0.1108 (4)	0.7338 (3)	0.0415 (9)
H7	0.2881	0.0693	0.7388	0.050*
C8	0.4479 (4)	0.1524 (3)	0.6264 (3)	0.0361 (9)
H8	0.4802	0.0761	0.5994	0.043*
C9	0.4631 (5)	0.0193 (4)	0.7917 (3)	0.0432 (10)
C10	0.5356 (5)	0.0573 (4)	0.8438 (3)	0.0504 (11)
H10	0.5227	0.1434	0.8444	0.060*
C11	0.6241 (5)	−0.0276 (5)	0.8933 (3)	0.0527 (11)
H11	0.6681	−0.0009	0.9298	0.063*
C12	0.6482 (5)	−0.1557 (5)	0.8888 (3)	0.0515 (11)
C13	0.5785 (5)	−0.1986 (4)	0.8381 (3)	0.0531 (11)
H13	0.5948	−0.2843	0.8356	0.064*
C14	0.4850 (6)	−0.1108 (4)	0.7920 (3)	0.0515 (11)
H14	0.4346	−0.1385	0.7600	0.062*
C15	0.5823 (5)	0.2136 (4)	0.6107 (3)	0.0381 (9)
C16	0.7253 (4)	0.1350 (4)	0.6175 (3)	0.0367 (9)
C17	0.7548 (5)	0.0049 (4)	0.6175 (3)	0.0405 (9)
H17	0.6842	−0.0355	0.6128	0.049*
C18	0.8901 (5)	−0.0637 (4)	0.6246 (3)	0.0459 (10)
H18	0.9105	−0.1506	0.6253	0.055*
C19	0.9931 (5)	−0.0026 (5)	0.6304 (3)	0.0492 (11)
C20	0.9676 (5)	0.1254 (5)	0.6281 (4)	0.0586 (12)
H20	1.0402	0.1661	0.6299	0.070*
C21	0.8325 (5)	0.1928 (4)	0.6229 (3)	0.0505 (11)
H21	0.8133	0.2794	0.6231	0.061*
C22	0.4667 (6)	0.3933 (4)	0.4049 (3)	0.0522 (12)
H22A	0.4143	0.4606	0.4385	0.063*
H22B	0.5650	0.3736	0.4122	0.063*
C23	0.4740 (5)	0.4419 (4)	0.3002 (3)	0.0536 (11)
C24	0.6085 (6)	0.4252 (6)	0.2325 (3)	0.0802 (15)
H24	0.6901	0.3778	0.2516	0.096*
C25	0.6180 (8)	0.4815 (7)	0.1348 (4)	0.104 (2)
H25	0.7072	0.4739	0.0887	0.125*
C26	0.4943 (8)	0.5483 (7)	0.1074 (5)	0.107 (2)
H26	0.5019	0.5860	0.0428	0.128*
C27	0.3586 (8)	0.5606 (6)	0.1743 (4)	0.0968 (19)
H27	0.2759	0.6044	0.1549	0.116*
C28	0.3505 (7)	0.5054 (5)	0.2706 (4)	0.0730 (14)
H28	0.2605	0.5111	0.3161	0.088*
O1S	0.9557 (8)	0.1188 (7)	−0.1456 (5)	0.074 (2)	0.50
H1S	1.0032	0.0910	−0.1934	0.111*	0.50
C1S	0.8587 (13)	0.2035 (12)	0.0448 (9)	0.094 (3)	0.50
H1SA	0.8591	0.2194	0.1044	0.140*	0.50
H1SB	0.7601	0.2175	0.0406	0.140*	0.50
H1SC	0.9141	0.2606	−0.0080	0.140*	0.50
C2S	0.9279 (11)	0.0628 (12)	0.0407 (7)	0.102 (3)	0.50
H2S	0.8407	0.0210	0.0627	0.123*	0.50
C3S	0.9874 (15)	0.0158 (17)	0.1296 (8)	0.105 (3)	0.50
H3SA	0.9109	0.0314	0.1855	0.157*	0.50
H3SB	1.0658	0.0608	0.1209	0.157*	0.50
H3SC	1.0226	−0.0743	0.1379	0.157*	0.50
C4S	0.9953 (12)	0.0358 (10)	−0.0620 (6)	0.080 (3)	0.50
H4SA	1.1002	0.0294	−0.0753	0.096*	0.50
H4SB	0.9761	−0.0485	−0.0581	0.096*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0452 (3)	0.1001 (5)	0.0905 (4)	0.0156 (3)	−0.0323 (3)	−0.0453 (3)
S1	0.0426 (5)	0.0263 (5)	0.0398 (5)	−0.0004 (4)	−0.0186 (4)	−0.0091 (4)
N1	0.0434 (19)	0.0303 (16)	0.0431 (19)	0.0047 (14)	−0.0192 (15)	−0.0130 (14)
N2	0.065 (2)	0.053 (2)	0.043 (2)	0.0141 (19)	−0.0238 (19)	−0.0227 (18)
N3	0.063 (3)	0.079 (3)	0.041 (2)	0.005 (2)	−0.015 (2)	0.000 (2)
O1	0.0464 (16)	0.0320 (14)	0.0445 (16)	0.0033 (12)	−0.0157 (13)	−0.0136 (12)
O2	0.0499 (17)	0.0474 (17)	0.0531 (18)	0.0008 (13)	−0.0270 (14)	−0.0144 (14)
O3	0.071 (2)	0.0261 (16)	0.089 (2)	−0.0052 (14)	−0.0386 (19)	−0.0098 (15)
O4	0.103 (3)	0.077 (3)	0.081 (3)	0.027 (2)	−0.037 (2)	−0.008 (2)
O5	0.090 (3)	0.113 (3)	0.062 (2)	0.012 (2)	−0.045 (2)	−0.009 (2)
C1	0.065 (3)	0.051 (3)	0.064 (3)	0.017 (2)	−0.030 (3)	−0.021 (2)
C2	0.072 (3)	0.057 (3)	0.083 (4)	0.032 (3)	−0.036 (3)	−0.032 (3)
C3	0.065 (3)	0.063 (3)	0.082 (4)	0.023 (3)	−0.023 (3)	−0.041 (3)
C4	0.058 (3)	0.070 (3)	0.062 (3)	0.008 (3)	−0.015 (2)	−0.036 (3)
C5	0.051 (3)	0.047 (2)	0.049 (3)	0.003 (2)	−0.015 (2)	−0.020 (2)
C6	0.043 (2)	0.035 (2)	0.049 (2)	0.0031 (18)	−0.0164 (19)	−0.0149 (18)
C7	0.048 (2)	0.039 (2)	0.040 (2)	−0.0067 (19)	−0.0151 (19)	−0.0073 (18)
C8	0.045 (2)	0.0266 (19)	0.040 (2)	0.0027 (17)	−0.0201 (18)	−0.0093 (16)
C9	0.052 (3)	0.042 (2)	0.035 (2)	−0.008 (2)	−0.0126 (19)	−0.0056 (18)
C10	0.061 (3)	0.048 (3)	0.046 (3)	−0.004 (2)	−0.022 (2)	−0.011 (2)
C11	0.058 (3)	0.060 (3)	0.045 (3)	−0.006 (2)	−0.022 (2)	−0.013 (2)
C12	0.048 (3)	0.057 (3)	0.039 (2)	−0.007 (2)	−0.009 (2)	0.004 (2)
C13	0.066 (3)	0.039 (2)	0.051 (3)	−0.006 (2)	−0.020 (2)	−0.002 (2)
C14	0.073 (3)	0.042 (2)	0.042 (2)	−0.011 (2)	−0.023 (2)	−0.0020 (19)
C15	0.048 (2)	0.032 (2)	0.039 (2)	−0.0071 (18)	−0.0152 (18)	−0.0088 (17)
C16	0.042 (2)	0.033 (2)	0.036 (2)	−0.0062 (17)	−0.0121 (18)	−0.0068 (17)
C17	0.044 (2)	0.037 (2)	0.044 (2)	−0.0057 (18)	−0.0153 (19)	−0.0110 (18)
C18	0.046 (2)	0.043 (2)	0.051 (3)	0.0029 (19)	−0.016 (2)	−0.017 (2)
C19	0.039 (2)	0.063 (3)	0.048 (3)	0.003 (2)	−0.018 (2)	−0.017 (2)
C20	0.047 (3)	0.059 (3)	0.078 (3)	−0.015 (2)	−0.019 (2)	−0.019 (3)
C21	0.052 (3)	0.038 (2)	0.068 (3)	−0.010 (2)	−0.021 (2)	−0.014 (2)
C22	0.082 (3)	0.036 (2)	0.049 (3)	−0.015 (2)	−0.031 (2)	−0.006 (2)
C23	0.087 (3)	0.029 (2)	0.052 (3)	−0.020 (2)	−0.027 (2)	−0.0031 (19)
C24	0.093 (4)	0.072 (4)	0.074 (3)	−0.038 (3)	−0.017 (3)	0.001 (3)
C25	0.134 (5)	0.105 (5)	0.062 (3)	−0.058 (4)	0.011 (3)	−0.010 (3)
C26	0.192 (7)	0.087 (5)	0.055 (3)	−0.064 (5)	−0.045 (3)	0.009 (3)
C27	0.152 (5)	0.065 (4)	0.086 (4)	−0.016 (4)	−0.073 (4)	0.010 (3)
C28	0.108 (4)	0.048 (3)	0.065 (3)	−0.003 (3)	−0.039 (3)	−0.005 (2)
O1S	0.057 (4)	0.083 (5)	0.078 (4)	−0.043 (4)	−0.034 (4)	0.031 (4)
C1S	0.061 (5)	0.139 (8)	0.070 (5)	−0.035 (6)	0.019 (4)	−0.033 (5)
C2S	0.079 (5)	0.144 (8)	0.077 (4)	−0.045 (5)	0.006 (4)	−0.021 (5)
C3S	0.081 (6)	0.151 (8)	0.078 (5)	−0.055 (6)	0.003 (5)	−0.018 (6)
C4S	0.061 (7)	0.087 (8)	0.083 (5)	−0.012 (6)	−0.019 (6)	−0.005 (5)

Geometric parameters (Å, º)

Br1—C19	1.898 (4)	C15—C16	1.486 (6)
S1—O2	1.421 (3)	C16—C21	1.373 (6)
S1—O1	1.433 (3)	C16—C17	1.395 (6)
S1—N1	1.654 (4)	C17—C18	1.387 (6)
S1—C22	1.780 (5)	C17—H17	0.9300
N1—C6	1.439 (5)	C18—C19	1.364 (6)
N1—C8	1.472 (5)	C18—H18	0.9300
N2—C5	1.376 (6)	C19—C20	1.367 (7)
N2—C7	1.466 (5)	C20—C21	1.375 (7)
N2—H2N	0.8600	C20—H20	0.9300
N3—O5	1.222 (6)	C21—H21	0.9300
N3—O4	1.230 (6)	C22—C23	1.497 (6)
N3—C12	1.457 (6)	C22—H22A	0.9700
O3—C15	1.219 (5)	C22—H22B	0.9700
C1—C6	1.385 (6)	C23—C28	1.390 (5)
C1—C2	1.390 (7)	C23—C24	1.396 (4)
C1—H1	0.9300	C24—C25	1.408 (5)
C2—C3	1.359 (7)	C24—H24	0.9300
C2—H2	0.9300	C25—C26	1.384 (6)
C3—C4	1.348 (7)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.394 (6)
C4—C5	1.383 (6)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.389 (5)
C5—C6	1.409 (6)	C27—H27	0.9300
C7—C9	1.482 (6)	C28—H28	0.9300
C7—C8	1.538 (6)	O1S—C4S	1.439 (5)
C7—H7	0.9800	O1S—H1S	0.8200
C8—C15	1.532 (6)	C1S—C2S	1.554 (7)
C8—H8	0.9800	C1S—H1SA	0.9600
C9—C14	1.397 (6)	C1S—H1SB	0.9600
C9—C10	1.397 (6)	C1S—H1SC	0.9600
C10—C11	1.352 (6)	C2S—C3S	1.535 (7)
C10—H10	0.9300	C2S—C4S	1.559 (7)
C11—C12	1.393 (7)	C2S—H2S	0.9800
C11—H11	0.9300	C3S—H3SA	0.9600
C12—C13	1.392 (7)	C3S—H3SB	0.9600
C13—C14	1.370 (6)	C3S—H3SC	0.9600
C13—H13	0.9300	C4S—H4SA	0.9700
C14—H14	0.9300	C4S—H4SB	0.9700
O2—S1—O1	118.06 (17)	C21—C16—C15	118.9 (3)
O2—S1—N1	108.66 (18)	C17—C16—C15	122.2 (4)
O1—S1—N1	106.25 (16)	C18—C17—C16	119.6 (4)
O2—S1—C22	109.5 (2)	C18—C17—H17	120.2
O1—S1—C22	108.0 (2)	C16—C17—H17	120.2
N1—S1—C22	105.75 (19)	C19—C18—C17	119.5 (4)
C6—N1—C8	119.2 (3)	C19—C18—H18	120.2
C6—N1—S1	120.9 (3)	C17—C18—H18	120.2
C8—N1—S1	117.3 (3)	C18—C19—C20	121.8 (4)
C5—N2—C7	118.1 (3)	C18—C19—Br1	119.8 (3)
C5—N2—H2N	120.9	C20—C19—Br1	118.3 (4)
C7—N2—H2N	120.9	C19—C20—C21	118.6 (4)
O5—N3—O4	123.5 (5)	C19—C20—H20	120.7
O5—N3—C12	118.7 (5)	C21—C20—H20	120.7
O4—N3—C12	117.8 (5)	C16—C21—C20	121.5 (4)
C6—C1—C2	121.5 (5)	C16—C21—H21	119.2
C6—C1—H1	119.3	C20—C21—H21	119.2
C2—C1—H1	119.3	C23—C22—S1	113.7 (3)
C3—C2—C1	119.4 (5)	C23—C22—H22A	108.8
C3—C2—H2	120.3	S1—C22—H22A	108.8
C1—C2—H2	120.3	C23—C22—H22B	108.8
C4—C3—C2	120.1 (4)	S1—C22—H22B	108.8
C4—C3—H3	120.0	H22A—C22—H22B	107.7
C2—C3—H3	120.0	C28—C23—C24	120.2 (5)
C3—C4—C5	122.5 (5)	C28—C23—C22	120.9 (4)
C3—C4—H4	118.7	C24—C23—C22	118.8 (4)
C5—C4—H4	118.7	C23—C24—C25	118.7 (6)
N2—C5—C4	120.9 (4)	C23—C24—H24	120.6
N2—C5—C6	120.6 (4)	C25—C24—H24	120.6
C4—C5—C6	118.5 (4)	C26—C25—C24	119.8 (6)
C1—C6—C5	118.0 (4)	C26—C25—H25	120.1
C1—C6—N1	123.9 (4)	C24—C25—H25	120.1
C5—C6—N1	118.1 (4)	C25—C26—C27	121.7 (6)
N2—C7—C9	111.6 (3)	C25—C26—H26	119.2
N2—C7—C8	107.3 (3)	C27—C26—H26	119.2
C9—C7—C8	114.4 (3)	C28—C27—C26	118.1 (6)
N2—C7—H7	107.8	C28—C27—H27	120.9
C9—C7—H7	107.8	C26—C27—H27	120.9
C8—C7—H7	107.8	C27—C28—C23	121.3 (6)
N1—C8—C15	111.3 (3)	C27—C28—H28	119.4
N1—C8—C7	108.9 (3)	C23—C28—H28	119.4
C15—C8—C7	112.0 (3)	C4S—O1S—H1S	109.5
N1—C8—H8	108.2	C2S—C1S—H1SA	109.5
C15—C8—H8	108.2	C2S—C1S—H1SB	109.5
C7—C8—H8	108.2	H1SA—C1S—H1SB	109.5
C14—C9—C10	117.7 (4)	C2S—C1S—H1SC	109.5
C14—C9—C7	119.2 (4)	H1SA—C1S—H1SC	109.5
C10—C9—C7	123.0 (4)	H1SB—C1S—H1SC	109.5
C11—C10—C9	121.9 (4)	C3S—C2S—C1S	103.0 (11)
C11—C10—H10	119.0	C3S—C2S—C4S	129.8 (10)
C9—C10—H10	119.0	C1S—C2S—C4S	115.9 (9)
C10—C11—C12	118.8 (4)	C3S—C2S—H2S	101.1
C10—C11—H11	120.6	C1S—C2S—H2S	101.1
C12—C11—H11	120.6	C4S—C2S—H2S	101.1
C13—C12—C11	121.5 (4)	C2S—C3S—H3SA	109.5
C13—C12—N3	119.6 (4)	C2S—C3S—H3SB	109.5
C11—C12—N3	118.9 (4)	H3SA—C3S—H3SB	109.5
C14—C13—C12	118.0 (4)	C2S—C3S—H3SC	109.5
C14—C13—H13	121.0	H3SA—C3S—H3SC	109.5
C12—C13—H13	121.0	H3SB—C3S—H3SC	109.5
C13—C14—C9	121.9 (4)	O1S—C4S—C2S	122.7 (9)
C13—C14—H14	119.0	O1S—C4S—H4SA	106.7
C9—C14—H14	119.0	C2S—C4S—H4SA	106.7
O3—C15—C16	120.2 (4)	O1S—C4S—H4SB	106.7
O3—C15—C8	118.1 (4)	C2S—C4S—H4SB	106.7
C16—C15—C8	121.7 (3)	H4SA—C4S—H4SB	106.6
C21—C16—C17	118.9 (4)
O2—S1—N1—C6	−52.2 (3)	O5—N3—C12—C13	−161.4 (5)
O1—S1—N1—C6	179.9 (3)	O4—N3—C12—C13	18.9 (7)
C22—S1—N1—C6	65.3 (4)	O5—N3—C12—C11	17.5 (7)
O2—S1—N1—C8	146.0 (3)	O4—N3—C12—C11	−162.1 (5)
O1—S1—N1—C8	18.0 (3)	C11—C12—C13—C14	0.3 (7)
C22—S1—N1—C8	−96.6 (3)	N3—C12—C13—C14	179.2 (4)
C6—C1—C2—C3	−1.0 (9)	C12—C13—C14—C9	2.5 (7)
C1—C2—C3—C4	0.1 (9)	C10—C9—C14—C13	−2.6 (7)
C2—C3—C4—C5	0.6 (9)	C7—C9—C14—C13	174.9 (4)
C7—N2—C5—C4	157.3 (4)	N1—C8—C15—O3	24.7 (5)
C7—N2—C5—C6	−25.4 (7)	C7—C8—C15—O3	−97.5 (4)
C3—C4—C5—N2	177.0 (5)	N1—C8—C15—C16	−155.2 (3)
C3—C4—C5—C6	−0.4 (8)	C7—C8—C15—C16	82.6 (4)
C2—C1—C6—C5	1.2 (8)	O3—C15—C16—C21	13.6 (6)
C2—C1—C6—N1	179.7 (5)	C8—C15—C16—C21	−166.5 (4)
N2—C5—C6—C1	−177.9 (5)	O3—C15—C16—C17	−165.7 (4)
C4—C5—C6—C1	−0.5 (7)	C8—C15—C16—C17	14.2 (6)
N2—C5—C6—N1	3.5 (6)	C21—C16—C17—C18	1.1 (6)
C4—C5—C6—N1	−179.1 (4)	C15—C16—C17—C18	−179.6 (4)
C8—N1—C6—C1	168.5 (4)	C16—C17—C18—C19	−0.7 (6)
S1—N1—C6—C1	7.0 (6)	C17—C18—C19—C20	−0.9 (7)
C8—N1—C6—C5	−13.0 (6)	C17—C18—C19—Br1	−178.5 (3)
S1—N1—C6—C5	−174.5 (3)	C18—C19—C20—C21	2.1 (8)
C5—N2—C7—C9	178.0 (4)	Br1—C19—C20—C21	179.7 (4)
C5—N2—C7—C8	52.0 (5)	C17—C16—C21—C20	0.2 (7)
C6—N1—C8—C15	−83.7 (4)	C15—C16—C21—C20	−179.2 (4)
S1—N1—C8—C15	78.5 (3)	C19—C20—C21—C16	−1.7 (7)
C6—N1—C8—C7	40.3 (5)	O2—S1—C22—C23	−48.3 (4)
S1—N1—C8—C7	−157.5 (3)	O1—S1—C22—C23	81.4 (4)
N2—C7—C8—N1	−57.0 (4)	N1—S1—C22—C23	−165.2 (3)
C9—C7—C8—N1	178.7 (3)	S1—C22—C23—C28	73.9 (5)
N2—C7—C8—C15	66.6 (4)	S1—C22—C23—C24	−107.6 (5)
C9—C7—C8—C15	−57.8 (4)	C28—C23—C24—C25	4.4 (8)
N2—C7—C9—C14	156.3 (4)	C22—C23—C24—C25	−174.0 (5)
C8—C7—C9—C14	−81.7 (5)	C23—C24—C25—C26	−2.1 (10)
N2—C7—C9—C10	−26.3 (6)	C24—C25—C26—C27	−0.7 (11)
C8—C7—C9—C10	95.7 (5)	C25—C26—C27—C28	1.1 (10)
C14—C9—C10—C11	−0.2 (7)	C26—C27—C28—C23	1.3 (9)
C7—C9—C10—C11	−177.6 (4)	C24—C23—C28—C27	−4.1 (8)
C9—C10—C11—C12	2.8 (7)	C22—C23—C28—C27	174.3 (5)
C10—C11—C12—C13	−2.9 (7)	C3S—C2S—C4S—O1S	−157.5 (12)
C10—C11—C12—N3	178.2 (4)	C1S—C2S—C4S—O1S	−20.6 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5^i	0.86	2.48	3.213 (6)	143
C8—H8···O1^ii	0.98	2.58	3.536 (5)	166
C17—H17···O1^ii	0.93	2.64	3.554 (5)	168
C22—H22A···O3^iii	0.97	2.25	2.995 (5)	133
C3—H3···O4^iv	0.93	2.77	3.637 (7)	155
C25—H25···O4^v	0.93	2.78	3.418 (7)	126
C3S—H3SB···O5^vi	0.96	2.52	3.33 (1)	142
C2—H2···O2^vii	0.93	2.64	3.496 (6)	153
C18—H18···O2^ii	0.93	2.74	3.353 (5)	124
C3S—H3SA···Br1^vi	0.96	2.77	3.63 (1)	150

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x−1, y+1, z; (v) x, y+1, z−1; (vi) −x+2, −y, −z+1; (vii) −x, −y+1, −z+1.