Benzaldehyde 1-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranos­yl)thio­semicarbazone

Zhang, S.-S.; Yang, B.; Li, H.-X.; Li, X.-M.

doi:10.1107/S1600536805030308

Benzaldehyde 1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazone

S.-S. Zhang, B. Yang, H.-X. Li and X.-M. Li

In the title compound, C₂₂H₂₇N₃O₉S, the six-membered pyranosyl ring adopts a chair conformation. The acetyl group opposite the thiosemicarbazone substituent occupies an axial position, while all other substituents are in equatorial positions. The molecules are linked by C—H

O hydrogen bonds into chains parallel to the b axis, and two additional C—H

O interactions provide further stability in a three-dimensional network.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030308/is6124sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030308/is6124Isup2.hkl Contains datablock I

CCDC reference: 287611

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.063
wR factor = 0.132
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.04 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C13

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.32 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H27 N3 O9 S

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.15
           From the CIF: _reflns_number_total               5040
           Count of symmetry unique reflns         2811
           Completeness (_total/calc)            179.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2229
           Fraction of Friedel pairs measured     0.793
           Are heavy atom types Z>Si present        yes

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

Comment top

In the title compound, (I), the bond lengths and angles of the xylopyranosyl ring are comparable to those in the related compounds 4-methoxybenzaldehyde 4-(2,3,4,6-tetra-O-acetyl-β-D– glucopyranosyl)thiosemicarbazone (Zhang et al., 2004) and benzaldehyde 1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiosemicarbazone (Yang et al., 2004). The acetyl group at atom C4 occupies an axial position, while all other substituents are in equatorial positions. The pyranosyl ring adopts a chair conformation, and atom S1 is in a synperiplanar position with respect to atom C1, the C1—N1—C15—S1 torsion angle being 8.7 (6)°.

In the crystal structure of (I), the molecules are linked by C11—H11B···O5ⁱⁱ hydrogen bonds (Table 2) into chains parallel to the b axis (Fig. 2). The packing is further stabilized by two additional C7—H7B···O10Bⁱ and C16—H16A···O9ⁱ interactions (Table 2), giving a three-dimensional framework.

Experimental top

The title compound was prepared according to the method described by Zhang et al. (2004).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of (I), showing the formation of chains along the b axis. Dashed lines indicate C—H···O hydrogen bonds.

Benzaldehyde 1-(2,3,4,6-tetra-O-acetyl-β-D– galactopyranosyl)thiosemicarbazone top

Crystal data top

C₂₂H₂₇N₃O₉S	F(000) = 536
M_r = 509.53	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.547 (5) Å	Cell parameters from 1389 reflections
b = 9.113 (4) Å	θ = 2.6–19.0°
c = 12.801 (5) Å	µ = 0.18 mm⁻¹
β = 101.651 (8)°	T = 293 K
V = 1319.3 (9) Å³	Needle, colorless
Z = 2	0.55 × 0.08 × 0.08 mm

Data collection top

Siemens SMART CCD area detector diffractometer	5040 independent reflections
Radiation source: fine-focus sealed tube	3120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.2°, θ_min = 1.6°
ω scans	h = −7→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.910, T_max = 0.986	l = −15→15
7435 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0433P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5040 reflections	Δρ_max = 0.19 e Å⁻³
316 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2229 Friedel paris
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (11)

Crystal data top

C₂₂H₂₇N₃O₉S	V = 1319.3 (9) Å³
M_r = 509.53	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.547 (5) Å	µ = 0.18 mm⁻¹
b = 9.113 (4) Å	T = 293 K
c = 12.801 (5) Å	0.55 × 0.08 × 0.08 mm
β = 101.651 (8)°

Data collection top

Siemens SMART CCD area detector diffractometer	5040 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3120 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.986	R_int = 0.030
7435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.132	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.18 e Å⁻³
5040 reflections	Absolute structure: Flack (1983), 2229 Friedel paris
316 parameters	Absolute structure parameter: 0.06 (11)
1 restraint

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.16605 (9)	0.20227 (13)	0.96169 (10)	0.0779 (4)
O1	−0.1073 (2)	0.4398 (3)	0.8421 (2)	0.0672 (8)
O2	−0.1962 (2)	0.1678 (3)	1.0197 (3)	0.0726 (8)
O3	−0.2033 (3)	0.3103 (4)	1.1606 (3)	0.1023 (11)
O4	−0.4102 (2)	0.2211 (3)	0.8765 (2)	0.0818 (9)
O5	−0.4155 (3)	−0.0010 (4)	0.8045 (3)	0.1005 (12)
O6	−0.3602 (2)	0.4916 (3)	0.7979 (2)	0.0755 (9)
O7	−0.5309 (3)	0.4461 (5)	0.6862 (4)	0.1372 (16)
O8	−0.2651 (4)	0.5056 (5)	0.5745 (3)	0.1051 (11)
O9	−0.3481 (5)	0.7213 (6)	0.5820 (5)	0.181 (3)
N1	−0.0077 (3)	0.3666 (4)	1.0105 (3)	0.0660 (9)
H1A	−0.0283	0.4318	1.0518	0.079*
N2	0.1599 (3)	0.3509 (4)	1.1353 (3)	0.0703 (10)
H2A	0.2315	0.3218	1.1575	0.084*
N3	0.1065 (3)	0.4364 (4)	1.2002 (3)	0.0648 (9)
C1	−0.0924 (3)	0.3242 (5)	0.9180 (3)	0.0649 (11)
H1B	−0.0643	0.2362	0.8867	0.078*
C2	−0.2108 (3)	0.2914 (5)	0.9484 (3)	0.0608 (10)
H2B	−0.2395	0.3771	0.9818	0.073*
C3	−0.2967 (3)	0.2486 (5)	0.8494 (4)	0.0688 (12)
H3B	−0.2690	0.1573	0.8222	0.083*
C4	−0.3076 (3)	0.3640 (5)	0.7632 (4)	0.0702 (12)
H4A	−0.3566	0.3271	0.6968	0.084*
C5	−0.1852 (4)	0.4024 (5)	0.7455 (4)	0.0699 (12)
H5A	−0.1530	0.3173	0.7143	0.084*
C6	−0.1919 (3)	0.1919 (6)	1.1244 (4)	0.0732 (12)
C7	−0.1730 (5)	0.0513 (6)	1.1853 (4)	0.0987 (17)
H7A	−0.1698	0.0704	1.2596	0.148*
H7B	−0.1000	0.0076	1.1765	0.148*
H7C	−0.2372	−0.0146	1.1591	0.148*
C8	−0.4606 (4)	0.0908 (6)	0.8489 (4)	0.0735 (13)
C9	−0.5771 (4)	0.0786 (8)	0.8817 (5)	0.132 (2)
H9A	−0.6114	−0.0155	0.8609	0.198*
H9B	−0.6289	0.1546	0.8477	0.198*
H9C	−0.5659	0.0890	0.9578	0.198*
C10	−0.4737 (4)	0.5219 (6)	0.7531 (5)	0.0897 (15)
C11	−0.5124 (4)	0.6577 (6)	0.7956 (5)	0.121 (2)
H11A	−0.5931	0.6770	0.7622	0.182*
H11B	−0.4634	0.7372	0.7814	0.182*
H11C	−0.5062	0.6481	0.8712	0.182*
C12	−0.1845 (4)	0.5328 (6)	0.6723 (4)	0.0876 (15)
H12A	−0.2077	0.6207	0.7056	0.105*
H12B	−0.1056	0.5476	0.6590	0.105*
C13	−0.3421 (7)	0.6100 (10)	0.5379 (5)	0.123 (2)
C14	−0.4214 (7)	0.5605 (10)	0.4359 (5)	0.197 (4)
H14A	−0.4768	0.6370	0.4095	0.295*
H14B	−0.4635	0.4739	0.4492	0.295*
H14C	−0.3745	0.5391	0.3838	0.295*
C15	0.1012 (3)	0.3117 (4)	1.0369 (3)	0.0598 (11)
C16	0.1638 (4)	0.4628 (5)	1.2942 (4)	0.0744 (13)
H16A	0.2388	0.4226	1.3160	0.089*
C17	0.1161 (5)	0.5526 (5)	1.3678 (4)	0.0795 (14)
C18	0.0034 (5)	0.6037 (6)	1.3424 (4)	0.0968 (16)
H18A	−0.0453	0.5753	1.2786	0.116*
C19	−0.0394 (7)	0.6966 (9)	1.4097 (6)	0.138 (2)
H19A	−0.1170	0.7299	1.3919	0.166*
C20	0.0325 (11)	0.7408 (10)	1.5040 (8)	0.161 (4)
H20A	0.0043	0.8047	1.5497	0.193*
C21	0.1428 (10)	0.6907 (10)	1.5286 (6)	0.159 (3)
H21A	0.1908	0.7210	1.5922	0.191*
C22	0.1891 (6)	0.5952 (8)	1.4634 (5)	0.113 (2)
H22A	0.2663	0.5607	1.4828	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0625 (6)	0.0779 (9)	0.1007 (8)	0.0222 (6)	0.0344 (6)	0.0112 (7)
O1	0.0507 (15)	0.0650 (19)	0.083 (2)	−0.0069 (14)	0.0073 (14)	−0.0107 (17)
O2	0.0694 (19)	0.058 (2)	0.093 (2)	0.0059 (14)	0.0239 (16)	−0.0122 (18)
O3	0.121 (3)	0.086 (3)	0.110 (3)	0.010 (2)	0.047 (2)	−0.024 (2)
O4	0.0499 (15)	0.078 (2)	0.123 (2)	−0.0088 (15)	0.0291 (15)	−0.0333 (19)
O5	0.079 (2)	0.080 (2)	0.150 (3)	−0.0252 (18)	0.042 (2)	−0.045 (2)
O6	0.0497 (16)	0.0609 (19)	0.109 (2)	0.0032 (14)	0.0003 (15)	−0.0298 (17)
O7	0.066 (2)	0.134 (4)	0.190 (4)	0.005 (2)	−0.025 (2)	−0.052 (3)
O8	0.120 (3)	0.099 (3)	0.084 (2)	−0.005 (2)	−0.008 (2)	−0.016 (2)
O9	0.205 (5)	0.103 (4)	0.191 (5)	0.013 (4)	−0.067 (4)	−0.007 (3)
N1	0.0445 (18)	0.067 (2)	0.088 (2)	0.0072 (16)	0.0161 (17)	−0.0135 (19)
N2	0.0465 (19)	0.078 (3)	0.087 (3)	0.0061 (18)	0.015 (2)	0.016 (2)
N3	0.059 (2)	0.060 (2)	0.077 (3)	−0.0045 (18)	0.019 (2)	0.019 (2)
C1	0.048 (2)	0.054 (3)	0.092 (3)	0.0017 (19)	0.014 (2)	−0.013 (2)
C2	0.049 (2)	0.051 (3)	0.085 (3)	0.0000 (19)	0.019 (2)	−0.012 (2)
C3	0.048 (2)	0.058 (3)	0.106 (3)	−0.0021 (19)	0.028 (2)	−0.025 (3)
C4	0.056 (3)	0.064 (3)	0.089 (3)	−0.002 (2)	0.009 (2)	−0.028 (3)
C5	0.062 (3)	0.067 (3)	0.082 (3)	−0.002 (2)	0.017 (2)	−0.025 (3)
C6	0.059 (2)	0.077 (4)	0.090 (3)	0.005 (3)	0.032 (2)	−0.018 (3)
C7	0.102 (4)	0.091 (4)	0.107 (4)	0.028 (3)	0.030 (3)	0.003 (3)
C8	0.055 (3)	0.080 (4)	0.085 (3)	−0.016 (2)	0.014 (2)	−0.017 (3)
C9	0.071 (3)	0.160 (6)	0.180 (6)	−0.048 (3)	0.062 (4)	−0.048 (5)
C10	0.050 (3)	0.082 (4)	0.132 (4)	−0.003 (3)	0.007 (3)	−0.020 (3)
C11	0.085 (3)	0.083 (4)	0.195 (6)	0.025 (3)	0.024 (4)	−0.012 (4)
C12	0.080 (3)	0.090 (4)	0.089 (3)	−0.003 (3)	0.007 (3)	−0.003 (3)
C13	0.135 (6)	0.105 (6)	0.108 (5)	−0.019 (5)	−0.028 (4)	0.010 (5)
C14	0.207 (8)	0.202 (9)	0.135 (5)	−0.016 (7)	−0.074 (6)	−0.008 (6)
C15	0.043 (2)	0.057 (3)	0.081 (3)	0.0014 (19)	0.019 (2)	0.016 (2)
C16	0.069 (3)	0.079 (4)	0.071 (3)	−0.007 (3)	0.005 (3)	0.023 (3)
C17	0.104 (4)	0.068 (3)	0.069 (3)	−0.017 (3)	0.024 (3)	0.017 (3)
C18	0.120 (5)	0.095 (4)	0.090 (4)	0.009 (3)	0.056 (4)	0.009 (3)
C19	0.183 (7)	0.129 (6)	0.125 (5)	0.007 (6)	0.081 (5)	0.014 (5)
C20	0.275 (13)	0.103 (6)	0.134 (8)	−0.001 (7)	0.110 (9)	−0.009 (5)
C21	0.280 (11)	0.121 (7)	0.078 (4)	−0.043 (8)	0.043 (7)	−0.006 (5)
C22	0.154 (6)	0.116 (5)	0.068 (4)	−0.024 (4)	0.019 (4)	0.013 (4)

Geometric parameters (Å, º) top

S1—C15	1.665 (4)	C6—C7	1.493 (6)
O1—C5	1.417 (5)	C7—H7A	0.9600
O1—C1	1.420 (5)	C7—H7B	0.9600
O2—C6	1.350 (5)	C7—H7C	0.9600
O2—C2	1.438 (5)	C8—C9	1.493 (6)
O3—C6	1.192 (5)	C9—H9A	0.9600
O4—C8	1.338 (5)	C9—H9B	0.9600
O4—C3	1.444 (4)	C9—H9C	0.9600
O5—C8	1.189 (5)	C10—C11	1.457 (7)
O6—C10	1.348 (5)	C11—H11A	0.9600
O6—C4	1.424 (5)	C11—H11B	0.9600
O7—C10	1.191 (5)	C11—H11C	0.9600
O8—C13	1.322 (8)	C12—H12A	0.9700
O8—C12	1.423 (5)	C12—H12B	0.9700
O9—C13	1.170 (8)	C13—C14	1.504 (8)
N1—C15	1.332 (5)	C14—H14A	0.9600
N1—C1	1.429 (5)	C14—H14B	0.9600
N1—H1A	0.8600	C14—H14C	0.9600
N2—C15	1.352 (5)	C16—C17	1.439 (7)
N2—N3	1.373 (5)	C16—H16A	0.9300
N2—H2A	0.8600	C17—C18	1.359 (7)
N3—C16	1.274 (5)	C17—C22	1.394 (7)
C1—C2	1.525 (5)	C18—C19	1.369 (8)
C1—H1B	0.9800	C18—H18A	0.9300
C2—C3	1.494 (5)	C19—C20	1.380 (10)
C2—H2B	0.9800	C19—H19A	0.9300
C3—C4	1.512 (6)	C20—C21	1.329 (10)
C3—H3B	0.9800	C20—H20A	0.9300
C4—C5	1.516 (5)	C21—C22	1.386 (10)
C4—H4A	0.9800	C21—H21A	0.9300
C5—C12	1.514 (6)	C22—H22A	0.9300
C5—H5A	0.9800

C5—O1—C1	112.7 (3)	C8—C9—H9A	109.5
C6—O2—C2	118.6 (3)	C8—C9—H9B	109.5
C8—O4—C3	117.2 (3)	H9A—C9—H9B	109.5
C10—O6—C4	118.3 (3)	C8—C9—H9C	109.5
C13—O8—C12	117.4 (5)	H9A—C9—H9C	109.5
C15—N1—C1	124.2 (4)	H9B—C9—H9C	109.5
C15—N1—H1A	117.9	O7—C10—O6	122.5 (5)
C1—N1—H1A	117.9	O7—C10—C11	126.4 (5)
C15—N2—N3	120.8 (3)	O6—C10—C11	111.2 (4)
C15—N2—H2A	119.6	C10—C11—H11A	109.5
N3—N2—H2A	119.6	C10—C11—H11B	109.5
C16—N3—N2	117.9 (4)	H11A—C11—H11B	109.5
O1—C1—N1	109.5 (3)	C10—C11—H11C	109.5
O1—C1—C2	109.2 (3)	H11A—C11—H11C	109.5
N1—C1—C2	109.9 (3)	H11B—C11—H11C	109.5
O1—C1—H1B	109.4	O8—C12—C5	108.9 (4)
N1—C1—H1B	109.4	O8—C12—H12A	109.9
C2—C1—H1B	109.4	C5—C12—H12A	109.9
O2—C2—C3	107.8 (3)	O8—C12—H12B	109.9
O2—C2—C1	108.6 (3)	C5—C12—H12B	109.9
C3—C2—C1	108.1 (3)	H12A—C12—H12B	108.3
O2—C2—H2B	110.7	O9—C13—O8	123.6 (6)
C3—C2—H2B	110.7	O9—C13—C14	126.5 (8)
C1—C2—H2B	110.7	O8—C13—C14	109.9 (8)
O4—C3—C2	108.7 (3)	C13—C14—H14A	109.5
O4—C3—C4	110.5 (3)	C13—C14—H14B	109.5
C2—C3—C4	112.4 (3)	H14A—C14—H14B	109.5
O4—C3—H3B	108.4	C13—C14—H14C	109.5
C2—C3—H3B	108.4	H14A—C14—H14C	109.5
C4—C3—H3B	108.4	H14B—C14—H14C	109.5
O6—C4—C3	108.6 (3)	N1—C15—N2	114.0 (4)
O6—C4—C5	109.1 (3)	N1—C15—S1	126.2 (3)
C3—C4—C5	109.1 (3)	N2—C15—S1	119.8 (3)
O6—C4—H4A	110.0	N3—C16—C17	122.1 (5)
C3—C4—H4A	110.0	N3—C16—H16A	119.0
C5—C4—H4A	110.0	C17—C16—H16A	119.0
O1—C5—C12	105.7 (3)	C18—C17—C22	119.7 (6)
O1—C5—C4	111.8 (3)	C18—C17—C16	120.9 (5)
C12—C5—C4	113.3 (4)	C22—C17—C16	119.3 (6)
O1—C5—H5A	108.6	C17—C18—C19	120.8 (6)
C12—C5—H5A	108.6	C17—C18—H18A	119.6
C4—C5—H5A	108.6	C19—C18—H18A	119.6
O3—C6—O2	123.3 (5)	C18—C19—C20	120.1 (8)
O3—C6—C7	126.2 (5)	C18—C19—H19A	119.9
O2—C6—C7	110.6 (4)	C20—C19—H19A	119.9
C6—C7—H7A	109.5	C21—C20—C19	119.0 (10)
C6—C7—H7B	109.5	C21—C20—H20A	120.5
H7A—C7—H7B	109.5	C19—C20—H20A	120.5
C6—C7—H7C	109.5	C20—C21—C22	122.8 (9)
H7A—C7—H7C	109.5	C20—C21—H21A	118.6
H7B—C7—H7C	109.5	C22—C21—H21A	118.6
O5—C8—O4	122.8 (4)	C21—C22—C17	117.7 (7)
O5—C8—C9	126.0 (5)	C21—C22—H22A	121.1
O4—C8—C9	111.1 (5)	C17—C22—H22A	121.1

C15—N2—N3—C16	176.1 (4)	C3—C4—C5—C12	−171.5 (4)
C5—O1—C1—N1	176.6 (3)	C2—O2—C6—O3	2.5 (6)
C5—O1—C1—C2	−63.0 (4)	C2—O2—C6—C7	−178.4 (3)
C15—N1—C1—O1	−108.2 (4)	C3—O4—C8—O5	0.5 (7)
C15—N1—C1—C2	131.9 (4)	C3—O4—C8—C9	−179.9 (4)
C6—O2—C2—C3	−138.3 (3)	C4—O6—C10—O7	0.1 (8)
C6—O2—C2—C1	104.9 (4)	C4—O6—C10—C11	−178.5 (5)
O1—C1—C2—O2	176.2 (3)	C13—O8—C12—C5	130.7 (5)
N1—C1—C2—O2	−63.7 (4)	O1—C5—C12—O8	−177.6 (3)
O1—C1—C2—C3	59.5 (4)	C4—C5—C12—O8	−54.9 (5)
N1—C1—C2—C3	179.6 (3)	C12—O8—C13—O9	−0.9 (11)
C8—O4—C3—C2	−125.4 (4)	C12—O8—C13—C14	−178.6 (6)
C8—O4—C3—C4	110.9 (4)	C1—N1—C15—N2	−170.6 (4)
O2—C2—C3—O4	64.4 (4)	C1—N1—C15—S1	8.7 (6)
C1—C2—C3—O4	−178.4 (3)	N3—N2—C15—N1	1.8 (5)
O2—C2—C3—C4	−173.0 (3)	N3—N2—C15—S1	−177.5 (3)
C1—C2—C3—C4	−55.8 (4)	N2—N3—C16—C17	179.2 (4)
C10—O6—C4—C3	−106.2 (4)	N3—C16—C17—C18	5.3 (7)
C10—O6—C4—C5	135.1 (4)	N3—C16—C17—C22	−170.6 (4)
O4—C3—C4—O6	54.9 (4)	C22—C17—C18—C19	0.0 (8)
C2—C3—C4—O6	−66.7 (4)	C16—C17—C18—C19	−175.9 (5)
O4—C3—C4—C5	173.7 (3)	C17—C18—C19—C20	0.8 (10)
C2—C3—C4—C5	52.1 (4)	C18—C19—C20—C21	−0.7 (12)
C1—O1—C5—C12	−176.4 (3)	C19—C20—C21—C22	−0.1 (14)
C1—O1—C5—C4	59.9 (4)	C20—C21—C22—C17	0.8 (12)
O6—C4—C5—O1	66.2 (5)	C18—C17—C22—C21	−0.7 (8)
C3—C4—C5—O1	−52.3 (4)	C16—C17—C22—C21	175.2 (5)
O6—C4—C5—C12	−53.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1ⁱ	0.96	2.53	3.477 (6)	169
C11—H11B···O5ⁱⁱ	0.96	2.45	3.300 (7)	147
C16—H16A···O9ⁱ	0.93	2.45	3.244 (8)	143

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇N₃O₉S
M_r	509.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.547 (5), 9.113 (4), 12.801 (5)
β (°)	101.651 (8)
V (Å³)	1319.3 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.55 × 0.08 × 0.08

Data collection
Diffractometer	Siemens SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.910, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7435, 5040, 3120
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.132, 1.06
No. of reflections	5040
No. of parameters	316
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18
Absolute structure	Flack (1983), 2229 Friedel paris
Absolute structure parameter	0.06 (11)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—C15	1.665 (4)	N1—C1	1.429 (5)
O1—C5	1.417 (5)	N2—C15	1.352 (5)
O1—C1	1.420 (5)	N2—N3	1.373 (5)
N1—C15	1.332 (5)	N3—C16	1.274 (5)

C1—N1—C15—N2	−170.6 (4)	C1—N1—C15—S1	8.7 (6)