Tetra­kis(1H-benzimidazole-κN³)(sulfato-κO)copper(II) dimethyl sulfoxide solvate

The title copper(II) compound, [Cu(SO₄)(C₇H₆N₂)₄]·(CH₃)₂SO, displays a square-pyramidal coordination geometry formed by four benzimidazole ligands and a sulfate anion. The mol­ecules are linked by N—H...O and C—H...O hydrogen bonds, forming an extensive two-dimensional network in the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.041
• wR factor = 0.092
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S1'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      43.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.60 Deg.
              S1   -O1   -S1'     1.555   1.555   1.555

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
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: P3 Software (Siemens, 1989); cell refinement: P3 Software; data reduction: XDISK in SHELXTL/PC (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Tetrakis(1H-benzimidazole-κN³)(sulfato-κO)copper(II) dimethyl sulfoxide solvate

Crystal data

[Cu(SO4)(C7H6N2)4]·C2H6OS	Z = 2
Mr = 710.31	F(000) = 734
Triclinic, P1	Dx = 1.516 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.347 (2) Å	Cell parameters from 40 reflections
b = 10.744 (2) Å	θ = 6–18°
c = 15.121 (3) Å	µ = 0.89 mm^−1
α = 98.99 (3)°	T = 293 K
β = 109.88 (3)°	Prism, blue
γ = 91.45 (3)°	0.40 × 0.30 × 0.15 mm
V = 1555.8 (6) Å^3

Data collection

Siemens P3 diffractometer	3972 reflections with I > 2σ(I)
Radiation source: FK60-10 Siemens Mo tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω–2θ scans	h = −12→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.68, Tmax = 0.87	l = −17→11
5683 measured reflections	3 standard reflections every 100 reflections
5456 independent reflections	intensity decay: none

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.1051P] where P = (Fo^2 + 2Fc^2)/3
5456 reflections	(Δ/σ)max = 0.001
424 parameters	Δρmax = 0.29 e Å^−3
6 restraints	Δρmin = −0.37 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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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)
Cu	0.66011 (4)	0.70148 (4)	0.80354 (3)	0.02359 (12)
S2	0.77893 (8)	0.79893 (7)	1.04424 (6)	0.02395 (19)
O2	0.7943 (2)	0.7367 (2)	0.95518 (16)	0.0351 (6)
O3	0.9035 (2)	0.7835 (2)	1.12601 (16)	0.0347 (6)
O4	0.7677 (2)	0.9361 (2)	1.04291 (17)	0.0326 (6)
O5	0.6543 (2)	0.7452 (2)	1.05482 (17)	0.0361 (6)
N11	0.5091 (3)	0.5868 (2)	0.80869 (19)	0.0273 (6)
N13	0.4072 (3)	0.4403 (2)	0.8567 (2)	0.0306 (7)
H13	0.3966	0.3858	0.8903	0.037*
N21	0.7596 (3)	0.5466 (2)	0.78425 (19)	0.0269 (6)
N23	0.9104 (3)	0.4024 (3)	0.8192 (2)	0.0322 (7)
H23	0.9794	0.3658	0.8515	0.039*
N31	0.7933 (3)	0.8143 (2)	0.7739 (2)	0.0275 (6)
N33	0.9363 (3)	0.9836 (3)	0.8003 (2)	0.0373 (7)
H33	0.9846	1.0539	0.8288	0.045*
N41	0.5383 (3)	0.8457 (2)	0.8044 (2)	0.0277 (6)
N43	0.4045 (3)	0.9700 (3)	0.8592 (2)	0.0336 (7)
H43	0.3598	1.0005	0.8951	0.040*
C12	0.5235 (3)	0.5114 (3)	0.8719 (2)	0.0300 (8)
H12	0.6056	0.5081	0.9217	0.036*
C14	0.3076 (3)	0.4702 (3)	0.7773 (2)	0.0278 (7)
C15	0.1701 (4)	0.4264 (3)	0.7303 (3)	0.0381 (9)
H15	0.1285	0.3637	0.7502	0.046*
C16	0.0983 (4)	0.4795 (4)	0.6532 (3)	0.0460 (10)
H16	0.0056	0.4530	0.6205	0.055*
C17	0.1611 (4)	0.5725 (4)	0.6227 (3)	0.0476 (10)
H17	0.1093	0.6067	0.5701	0.057*
C18	0.2976 (4)	0.6147 (3)	0.6686 (3)	0.0365 (8)
H18	0.3389	0.6763	0.6475	0.044*
C19	0.3720 (3)	0.5632 (3)	0.7470 (2)	0.0262 (7)
C22	0.8685 (3)	0.5132 (3)	0.8494 (2)	0.0286 (7)
H22	0.9116	0.5613	0.9098	0.034*
C24	0.8227 (3)	0.3580 (3)	0.7273 (2)	0.0296 (8)
C25	0.8212 (4)	0.2524 (3)	0.6608 (3)	0.0463 (10)
H25	0.8869	0.1941	0.6753	0.056*
C26	0.7191 (5)	0.2377 (4)	0.5734 (3)	0.0546 (11)
H26	0.7162	0.1687	0.5269	0.066*
C27	0.6189 (4)	0.3243 (4)	0.5521 (3)	0.0506 (10)
H27	0.5490	0.3100	0.4926	0.061*
C28	0.6216 (4)	0.4302 (3)	0.6176 (3)	0.0397 (9)
H28	0.5551	0.4877	0.6031	0.048*
C29	0.7267 (3)	0.4480 (3)	0.7056 (2)	0.0291 (8)
C32	0.8557 (3)	0.9186 (3)	0.8333 (3)	0.0327 (8)
H32	0.8450	0.9444	0.8919	0.039*
C34	0.9281 (3)	0.9175 (3)	0.7126 (3)	0.0312 (8)
C35	0.9898 (4)	0.9398 (4)	0.6479 (3)	0.0474 (10)
H35	1.0524	1.0096	0.6606	0.057*
C36	0.9547 (5)	0.8548 (4)	0.5642 (3)	0.0579 (12)
H36	0.9928	0.8678	0.5186	0.070*
C37	0.8622 (5)	0.7485 (4)	0.5463 (3)	0.0515 (11)
H37	0.8404	0.6927	0.4887	0.062*
C38	0.8029 (4)	0.7242 (3)	0.6112 (3)	0.0375 (9)
H38	0.7427	0.6527	0.5990	0.045*
C39	0.8363 (3)	0.8106 (3)	0.6957 (2)	0.0289 (7)
C42	0.4798 (3)	0.8705 (3)	0.8698 (2)	0.0272 (7)
H42	0.4900	0.8236	0.9181	0.033*
C44	0.4118 (3)	1.0150 (3)	0.7800 (2)	0.0304 (8)
C45	0.3547 (4)	1.1160 (3)	0.7382 (3)	0.0422 (9)
H45	0.2994	1.1679	0.7622	0.051*
C46	0.3844 (5)	1.1348 (4)	0.6597 (3)	0.0523 (11)
H46	0.3483	1.2018	0.6295	0.063*
C47	0.4666 (4)	1.0574 (4)	0.6233 (3)	0.0513 (11)
H47	0.4837	1.0735	0.5694	0.062*
C48	0.5234 (4)	0.9575 (3)	0.6652 (2)	0.0366 (8)
H48	0.5782	0.9059	0.6405	0.044*
C49	0.4960 (3)	0.9361 (3)	0.7458 (2)	0.0274 (7)
O1	0.8066 (3)	0.4365 (2)	0.0227 (2)	0.0553 (8)
S1	0.74237 (12)	0.31685 (11)	0.03301 (9)	0.0431 (3)	0.85
C1	0.8628 (5)	0.2552 (4)	0.1237 (4)	0.0746 (15)	0.85
H1A	0.8791	0.3097	0.1838	0.112*	0.85
H1B	0.9476	0.2493	0.1112	0.112*	0.85
H1C	0.8281	0.1725	0.1260	0.112*	0.85
C2	0.7322 (8)	0.2025 (5)	−0.0662 (4)	0.109 (2)	0.85
H2A	0.6678	0.2249	−0.1229	0.164*	0.85
H2B	0.7017	0.1215	−0.0577	0.164*	0.85
H2C	0.8214	0.1984	−0.0723	0.164*	0.85
S1'	0.8380 (7)	0.2920 (7)	0.0109 (5)	0.0528 (18)	0.15
C1'	0.8628 (5)	0.2552 (4)	0.1237 (4)	0.0746 (15)	0.15
H1'1	0.9316	0.3150	0.1714	0.112*	0.15
H1'2	0.8929	0.1716	0.1259	0.112*	0.15
H1'3	0.7776	0.2588	0.1358	0.112*	0.15
C2'	0.7322 (8)	0.2025 (5)	−0.0662 (4)	0.109 (2)	0.15
H2'1	0.7220	0.2254	−0.1269	0.164*	0.15
H2'2	0.6456	0.2060	−0.0560	0.164*	0.15
H2'3	0.7606	0.1182	−0.0655	0.164*	0.15

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0241 (2)	0.0173 (2)	0.0310 (2)	0.00388 (15)	0.01084 (18)	0.00580 (16)
S2	0.0275 (4)	0.0188 (4)	0.0265 (5)	0.0056 (3)	0.0098 (4)	0.0053 (3)
O2	0.0457 (15)	0.0334 (13)	0.0265 (13)	0.0129 (11)	0.0143 (11)	0.0007 (10)
O3	0.0354 (13)	0.0280 (13)	0.0312 (14)	0.0065 (10)	−0.0008 (11)	0.0055 (11)
O4	0.0389 (14)	0.0186 (12)	0.0444 (15)	0.0063 (10)	0.0189 (12)	0.0073 (10)
O5	0.0342 (13)	0.0330 (13)	0.0457 (15)	−0.0006 (10)	0.0163 (12)	0.0151 (12)
N11	0.0278 (15)	0.0217 (14)	0.0352 (17)	0.0053 (11)	0.0114 (13)	0.0114 (13)
N13	0.0350 (16)	0.0251 (15)	0.0361 (18)	0.0019 (12)	0.0149 (14)	0.0126 (13)
N21	0.0254 (15)	0.0219 (14)	0.0315 (16)	0.0028 (11)	0.0088 (13)	0.0016 (12)
N23	0.0278 (15)	0.0314 (16)	0.0396 (18)	0.0143 (12)	0.0113 (14)	0.0116 (14)
N31	0.0271 (15)	0.0217 (14)	0.0346 (17)	0.0022 (11)	0.0124 (13)	0.0037 (12)
N33	0.0361 (17)	0.0277 (16)	0.0442 (19)	−0.0065 (13)	0.0106 (15)	0.0039 (14)
N41	0.0290 (15)	0.0241 (14)	0.0344 (17)	0.0074 (12)	0.0138 (13)	0.0108 (12)
N43	0.0381 (17)	0.0317 (16)	0.0381 (18)	0.0145 (13)	0.0200 (14)	0.0100 (14)
C12	0.0303 (18)	0.0267 (18)	0.033 (2)	0.0035 (14)	0.0084 (15)	0.0120 (15)
C14	0.0294 (18)	0.0274 (18)	0.0264 (18)	0.0023 (14)	0.0104 (15)	0.0026 (14)
C15	0.033 (2)	0.036 (2)	0.043 (2)	−0.0048 (16)	0.0148 (18)	−0.0007 (17)
C16	0.029 (2)	0.055 (3)	0.042 (2)	−0.0031 (18)	0.0036 (18)	−0.001 (2)
C17	0.039 (2)	0.055 (3)	0.039 (2)	0.0079 (19)	−0.0002 (18)	0.012 (2)
C18	0.039 (2)	0.035 (2)	0.036 (2)	0.0019 (16)	0.0103 (17)	0.0123 (17)
C19	0.0282 (17)	0.0187 (16)	0.0317 (19)	0.0022 (13)	0.0107 (15)	0.0041 (14)
C22	0.0283 (18)	0.0281 (18)	0.0313 (19)	0.0039 (14)	0.0119 (15)	0.0069 (15)
C24	0.0324 (19)	0.0230 (17)	0.037 (2)	0.0028 (14)	0.0160 (17)	0.0051 (15)
C25	0.055 (3)	0.030 (2)	0.058 (3)	0.0096 (18)	0.027 (2)	0.0031 (19)
C26	0.071 (3)	0.035 (2)	0.053 (3)	−0.002 (2)	0.022 (2)	−0.010 (2)
C27	0.057 (3)	0.045 (2)	0.037 (2)	−0.007 (2)	0.004 (2)	−0.0022 (19)
C28	0.038 (2)	0.031 (2)	0.043 (2)	0.0049 (16)	0.0044 (18)	0.0068 (17)
C29	0.0321 (19)	0.0231 (17)	0.035 (2)	0.0038 (14)	0.0150 (16)	0.0049 (15)
C32	0.037 (2)	0.0273 (19)	0.035 (2)	0.0043 (15)	0.0145 (17)	0.0055 (16)
C34	0.0313 (19)	0.0265 (18)	0.039 (2)	0.0063 (14)	0.0144 (16)	0.0101 (16)
C35	0.051 (2)	0.043 (2)	0.064 (3)	0.0086 (19)	0.034 (2)	0.024 (2)
C36	0.079 (3)	0.060 (3)	0.064 (3)	0.023 (2)	0.053 (3)	0.029 (3)
C37	0.073 (3)	0.052 (3)	0.036 (2)	0.025 (2)	0.024 (2)	0.011 (2)
C38	0.043 (2)	0.032 (2)	0.036 (2)	0.0054 (16)	0.0124 (18)	0.0043 (17)
C39	0.0273 (17)	0.0288 (18)	0.0328 (19)	0.0086 (14)	0.0104 (15)	0.0109 (15)
C42	0.0289 (18)	0.0230 (17)	0.0333 (19)	0.0067 (14)	0.0126 (15)	0.0104 (15)
C44	0.0328 (19)	0.0253 (18)	0.031 (2)	0.0059 (14)	0.0096 (16)	0.0034 (15)
C45	0.048 (2)	0.034 (2)	0.047 (2)	0.0208 (18)	0.0164 (19)	0.0129 (18)
C46	0.074 (3)	0.037 (2)	0.048 (3)	0.022 (2)	0.016 (2)	0.022 (2)
C47	0.070 (3)	0.053 (3)	0.038 (2)	0.016 (2)	0.020 (2)	0.021 (2)
C48	0.045 (2)	0.036 (2)	0.032 (2)	0.0088 (17)	0.0164 (17)	0.0086 (17)
C49	0.0277 (18)	0.0217 (17)	0.0306 (19)	0.0031 (13)	0.0068 (15)	0.0054 (14)
O1	0.0577 (18)	0.0370 (15)	0.066 (2)	0.0037 (13)	0.0088 (15)	0.0220 (14)
S1	0.0341 (6)	0.0375 (6)	0.0558 (8)	0.0062 (5)	0.0105 (6)	0.0142 (6)
C1	0.076 (3)	0.047 (3)	0.089 (4)	0.001 (2)	0.006 (3)	0.033 (3)
C2	0.191 (7)	0.045 (3)	0.088 (4)	−0.001 (4)	0.050 (5)	0.000 (3)
S1'	0.035 (4)	0.067 (5)	0.054 (5)	−0.004 (3)	0.011 (3)	0.016 (4)
C1'	0.076 (3)	0.047 (3)	0.089 (4)	0.001 (2)	0.006 (3)	0.033 (3)
C2'	0.191 (7)	0.045 (3)	0.088 (4)	−0.001 (4)	0.050 (5)	0.000 (3)

Geometric parameters (Å, º)

Cu—N11	1.995 (3)	C24—C29	1.398 (4)
Cu—N21	2.013 (3)	C25—C26	1.366 (6)
Cu—N31	2.019 (3)	C25—H25	0.9300
Cu—N41	2.023 (3)	C26—C27	1.400 (6)
Cu—O2	2.206 (2)	C26—H26	0.9300
S2—O5	1.468 (2)	C27—C28	1.380 (5)
S2—O2	1.468 (2)	C27—H27	0.9300
S2—O4	1.484 (2)	C28—C29	1.384 (5)
S2—O3	1.486 (2)	C28—H28	0.9300
N11—C12	1.320 (4)	C32—H32	0.9300
N11—C19	1.397 (4)	C34—C35	1.383 (5)
N13—C12	1.340 (4)	C34—C39	1.405 (5)
N13—C14	1.379 (4)	C35—C36	1.370 (6)
N13—H13	0.8600	C35—H35	0.9300
N21—C22	1.320 (4)	C36—C37	1.401 (6)
N21—C29	1.401 (4)	C36—H36	0.9300
N23—C22	1.343 (4)	C37—C38	1.375 (5)
N23—C24	1.376 (4)	C37—H37	0.9300
N23—H23	0.8600	C38—C39	1.388 (5)
N31—C32	1.316 (4)	C38—H38	0.9300
N31—C39	1.394 (4)	C42—H42	0.9300
N33—C32	1.339 (4)	C44—C45	1.385 (5)
N33—C34	1.376 (4)	C44—C49	1.397 (4)
N33—H33	0.8600	C45—C46	1.365 (5)
N41—C42	1.322 (4)	C45—H45	0.9300
N41—C49	1.396 (4)	C46—C47	1.390 (5)
N43—C42	1.336 (4)	C46—H46	0.9300
N43—C44	1.384 (4)	C47—C48	1.375 (5)
N43—H43	0.8600	C47—H47	0.9300
C12—H12	0.9300	C48—C49	1.391 (5)
C14—C15	1.388 (5)	C48—H48	0.9300
C14—C19	1.404 (4)	O1—S1	1.486 (3)
C15—C16	1.370 (5)	O1—S1'	1.589 (8)
C15—H15	0.9300	S1—C1	1.742 (5)
C16—C17	1.396 (5)	S1—C2	1.756 (5)
C16—H16	0.9300	C1—H1A	0.9600
C17—C18	1.373 (5)	C1—H1B	0.9600
C17—H17	0.9300	C1—H1C	0.9600
C18—C19	1.383 (5)	C2—H2A	0.9600
C18—H18	0.9300	C2—H2B	0.9600
C22—H22	0.9300	C2—H2C	0.9600
C24—C25	1.390 (5)
N11—Cu—N21	87.64 (11)	C25—C26—C27	121.4 (4)
N11—Cu—N31	170.01 (11)	C25—C26—H26	119.3
N21—Cu—N31	92.95 (11)	C27—C26—H26	119.3
N11—Cu—N41	88.46 (10)	C28—C27—C26	121.4 (4)
N21—Cu—N41	171.54 (11)	C28—C27—H27	119.3
N31—Cu—N41	89.60 (11)	C26—C27—H27	119.3
N11—Cu—O2	100.22 (11)	C27—C28—C29	117.8 (3)
N21—Cu—O2	88.36 (10)	C27—C28—H28	121.1
N31—Cu—O2	89.77 (11)	C29—C28—H28	121.1
N41—Cu—O2	99.73 (10)	C28—C29—C24	120.2 (3)
O5—S2—O2	110.59 (15)	C28—C29—N21	131.1 (3)
O5—S2—O4	108.72 (13)	C24—C29—N21	108.7 (3)
O2—S2—O4	109.52 (14)	N31—C32—N33	112.8 (3)
O5—S2—O3	110.60 (14)	N31—C32—H32	123.6
O2—S2—O3	109.00 (14)	N33—C32—H32	123.6
O4—S2—O3	108.37 (14)	N33—C34—C35	132.5 (3)
S2—O2—Cu	134.46 (14)	N33—C34—C39	105.4 (3)
C12—N11—C19	105.6 (3)	C35—C34—C39	122.1 (4)
C12—N11—Cu	124.9 (2)	C36—C35—C34	117.2 (4)
C19—N11—Cu	129.3 (2)	C36—C35—H35	121.4
C12—N13—C14	107.5 (3)	C34—C35—H35	121.4
C12—N13—H13	126.3	C35—C36—C37	121.1 (4)
C14—N13—H13	126.3	C35—C36—H36	119.4
C22—N21—C29	105.1 (3)	C37—C36—H36	119.4
C22—N21—Cu	125.2 (2)	C38—C37—C36	122.0 (4)
C29—N21—Cu	129.5 (2)	C38—C37—H37	119.0
C22—N23—C24	107.5 (3)	C36—C37—H37	119.0
C22—N23—H23	126.2	C37—C38—C39	117.4 (4)
C24—N23—H23	126.2	C37—C38—H38	121.3
C32—N31—C39	105.6 (3)	C39—C38—H38	121.3
C32—N31—Cu	121.1 (2)	C38—C39—N31	131.4 (3)
C39—N31—Cu	133.2 (2)	C38—C39—C34	120.2 (3)
C32—N33—C34	107.8 (3)	N31—C39—C34	108.4 (3)
C32—N33—H33	126.1	N41—C42—N43	113.0 (3)
C34—N33—H33	126.1	N41—C42—H42	123.5
C42—N41—C49	105.2 (3)	N43—C42—H42	123.5
C42—N41—Cu	121.8 (2)	N43—C44—C45	131.4 (3)
C49—N41—Cu	133.0 (2)	N43—C44—C49	105.5 (3)
C42—N43—C44	107.5 (3)	C45—C44—C49	123.1 (3)
C42—N43—H43	126.3	C46—C45—C44	116.1 (3)
C44—N43—H43	126.3	C46—C45—H45	121.9
N11—C12—N13	112.8 (3)	C44—C45—H45	121.9
N11—C12—H12	123.6	C45—C46—C47	122.3 (4)
N13—C12—H12	123.6	C45—C46—H46	118.9
N13—C14—C15	132.2 (3)	C47—C46—H46	118.9
N13—C14—C19	105.8 (3)	C48—C47—C46	121.4 (4)
C15—C14—C19	122.0 (3)	C48—C47—H47	119.3
C16—C15—C14	117.0 (3)	C46—C47—H47	119.3
C16—C15—H15	121.5	C47—C48—C49	117.9 (3)
C14—C15—H15	121.5	C47—C48—H48	121.1
C15—C16—C17	121.5 (4)	C49—C48—H48	121.1
C15—C16—H16	119.2	C48—C49—N41	131.9 (3)
C17—C16—H16	119.2	C48—C49—C44	119.3 (3)
C18—C17—C16	121.5 (4)	N41—C49—C44	108.8 (3)
C18—C17—H17	119.3	S1—O1—S1'	44.6 (3)
C16—C17—H17	119.3	O1—S1—C1	108.0 (2)
C17—C18—C19	118.1 (3)	O1—S1—C2	107.6 (2)
C17—C18—H18	120.9	C1—S1—C2	100.2 (3)
C19—C18—H18	120.9	S1—C1—H1A	109.5
C18—C19—N11	131.9 (3)	S1—C1—H1B	109.5
C18—C19—C14	119.9 (3)	H1A—C1—H1B	109.5
N11—C19—C14	108.2 (3)	S1—C1—H1C	109.5
N21—C22—N23	113.0 (3)	H1A—C1—H1C	109.5
N21—C22—H22	123.5	H1B—C1—H1C	109.5
N23—C22—H22	123.5	S1—C2—H2A	109.5
N23—C24—C25	132.3 (3)	S1—C2—H2B	109.5
N23—C24—C29	105.7 (3)	H2A—C2—H2B	109.5
C25—C24—C29	121.9 (3)	S1—C2—H2C	109.5
C26—C25—C24	117.2 (4)	H2A—C2—H2C	109.5
C26—C25—H25	121.4	H2B—C2—H2C	109.5
C24—C25—H25	121.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O5^i	0.86	1.89	2.741 (3)	170
N23—H23···O3^ii	0.86	2.04	2.830 (4)	153
N33—H33···O3^iii	0.86	1.96	2.813 (4)	171
N43—H43···O4^iv	0.86	1.94	2.793 (4)	171
C12—H12···O1^v	0.93	2.35	3.253 (4)	163
C22—H22···O2	0.93	2.40	2.941 (4)	117
C42—H42···O5	0.93	2.47	3.282 (4)	146

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