3-(3,4-Methyl­ene­dioxy­phenyl)-1-(2-furyl)-3-(p-toluene­sulfonyl­amino)propan-1-one

The S atom of the sulfonyl group in the title compound, C₂₁H₁₉NO₆S, has a distorted tetrahedral geometry. The amino groups and sulfonyl groups are connected by intermolecular N—H...O hydrogen bonds. The furan ring is disordered in one of the two independent mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.061
• wR factor = 0.195
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O7'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C25'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT410_ALERT_2_C Short Intra H...H Contact  H24A   ..  H27B    ..       1.97 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      10.00 Deg.
              C25' -C26  -C25     1.555   1.555   1.555

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

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(3,4-Methylenedioxyphenyl)-1-(2-furyl)-3-(p-toluenesulfonylamino) propan-1-one

Crystal data

C21H19NO6S	F(000) = 1728
Mr = 413.44	Dx = 1.396 Mg m^−3
Monoclinic, P21/n	Melting point: 399 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.721 (4) Å	Cell parameters from 890 reflections
b = 12.082 (3) Å	θ = 2.5–21.0°
c = 21.386 (6) Å	µ = 0.20 mm^−1
β = 104.346 (6)°	T = 293 K
V = 3935.4 (18) Å^3	Prism, colorless
Z = 8	0.30 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area detector diffractometer	6939 independent reflections
Radiation source: fine-focus sealed tube	3691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
Tmin = 0.943, Tmax = 0.956	k = −14→14
20215 measured reflections	l = −25→19

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.195	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 4.1226P] where P = (Fo^2 + 2Fc^2)/3
6939 reflections	(Δ/σ)max = 0.002
560 parameters	Δρmax = 0.50 e Å^−3
121 restraints	Δρmin = −0.79 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)
S1	0.56657 (7)	0.82627 (10)	0.02291 (5)	0.0559 (3)
N1	0.5171 (2)	0.8854 (3)	0.07182 (16)	0.0554 (9)
H1	0.4767	0.9335	0.0572	0.066*
O2	0.4204 (2)	0.6706 (3)	0.1288 (2)	0.0933 (12)
O3	0.5326 (2)	0.8822 (3)	−0.03770 (15)	0.0769 (10)
O4	0.5562 (2)	0.7098 (3)	0.02548 (16)	0.0740 (10)
O5	0.8036 (2)	1.1285 (3)	0.29030 (18)	0.0814 (11)
O6	0.8352 (2)	0.9450 (3)	0.27926 (17)	0.0775 (10)
O1	0.2515 (3)	0.7159 (4)	0.0670 (2)	0.1051 (13)
C1	0.1731 (4)	0.7685 (7)	0.0427 (3)	0.120 (2)
H1A	0.1236	0.7330	0.0180	0.144*
C2	0.1747 (4)	0.8739 (6)	0.0578 (3)	0.120 (2)
H2A	0.1289	0.9244	0.0465	0.144*
C3	0.2643 (3)	0.8949 (5)	0.0961 (3)	0.0894 (17)
H3A	0.2870	0.9617	0.1145	0.107*
C4	0.3065 (3)	0.7987 (4)	0.0992 (2)	0.0690 (14)
C5	0.3948 (3)	0.7649 (5)	0.1294 (2)	0.0673 (14)
C6	0.4563 (3)	0.8534 (4)	0.1650 (2)	0.0686 (14)
H6A	0.4713	0.8376	0.2109	0.082*
H6B	0.4272	0.9248	0.1584	0.082*
C7	0.5401 (3)	0.8580 (4)	0.1410 (2)	0.0528 (11)
H7A	0.5657	0.7836	0.1456	0.063*
C8	0.6084 (3)	0.9363 (3)	0.18024 (19)	0.0458 (10)
C9	0.6902 (3)	0.8955 (3)	0.21163 (19)	0.0510 (11)
H9A	0.7032	0.8208	0.2094	0.061*
C10	0.7506 (2)	0.9669 (3)	0.2456 (2)	0.0473 (10)
C11	0.7320 (3)	1.0763 (3)	0.2513 (2)	0.0548 (11)
C12	0.6529 (3)	1.1208 (4)	0.2214 (2)	0.0610 (12)
H12A	0.6410	1.1957	0.2247	0.073*
C13	0.5902 (3)	1.0481 (3)	0.1853 (2)	0.0548 (11)
H13A	0.5352	1.0752	0.1642	0.066*
C14	0.8729 (3)	1.0513 (4)	0.2990 (3)	0.0924 (19)
H14A	0.9052	1.0492	0.3439	0.111*
H14B	0.9131	1.0721	0.2731	0.111*
C15	0.6789 (3)	0.8553 (4)	0.0502 (2)	0.0507 (11)
C16	0.7375 (3)	0.7707 (4)	0.0714 (2)	0.0675 (13)
H16A	0.7179	0.6979	0.0695	0.081*
C17	0.8252 (3)	0.7944 (5)	0.0954 (3)	0.0869 (18)
H17A	0.8644	0.7366	0.1095	0.104*
C18	0.8557 (3)	0.8992 (7)	0.0991 (3)	0.0911 (19)
C19	0.7967 (4)	0.9842 (5)	0.0785 (3)	0.0933 (19)
H19A	0.8167	1.0569	0.0814	0.112*
C20	0.7082 (3)	0.9630 (4)	0.0535 (3)	0.0764 (15)
H20A	0.6692	1.0207	0.0391	0.092*
C21	0.9518 (4)	0.9249 (5)	0.1256 (3)	0.102
H21A	0.9710	0.8964	0.1687	0.153*
H21B	0.9604	1.0036	0.1262	0.153*
H21C	0.9852	0.8910	0.0988	0.153*
S2	0.06405 (7)	0.32287 (9)	0.04043 (5)	0.0516 (3)
N2	0.0220 (2)	0.4145 (3)	0.07873 (16)	0.0519 (9)
H2	−0.0096	0.4659	0.0565	0.062*
O8	−0.0858 (2)	0.2518 (3)	0.1723 (2)	0.0920 (12)
O9	0.0405 (2)	0.3611 (3)	−0.02497 (14)	0.0703 (9)
O10	0.03600 (19)	0.2163 (2)	0.05476 (16)	0.0703 (9)
O11	0.3244 (2)	0.6856 (2)	0.25765 (16)	0.0717 (9)
O12	0.3388 (2)	0.4983 (3)	0.27411 (18)	0.0824 (11)
O7	−0.2654 (8)	0.2761 (9)	0.1020 (7)	0.088 (4)	0.62 (2)
C22	−0.3406 (8)	0.3320 (14)	0.0661 (8)	0.090 (4)	0.62 (2)
H22A	−0.3942	0.2965	0.0504	0.108*	0.62 (2)
C23	−0.3294 (8)	0.4389 (14)	0.0562 (7)	0.093 (4)	0.62 (2)
H23A	−0.3710	0.4886	0.0336	0.112*	0.62 (2)
C24	−0.2360 (10)	0.4624 (12)	0.0890 (12)	0.085 (6)	0.62 (2)
H24A	−0.2068	0.5299	0.0926	0.102*	0.62 (2)
C25	−0.2038 (9)	0.3639 (13)	0.1120 (15)	0.068 (5)	0.62 (2)
O7'	−0.2471 (10)	0.4344 (15)	0.0805 (11)	0.071 (5)	0.38 (2)
C22'	−0.3307 (10)	0.3858 (17)	0.0543 (10)	0.064 (6)	0.38 (2)
H22B	−0.3759	0.4227	0.0255	0.077*	0.38 (2)
C23'	−0.3387 (10)	0.2823 (15)	0.0746 (10)	0.070 (5)	0.38 (2)
H23B	−0.3883	0.2376	0.0639	0.084*	0.38 (2)
C24'	−0.2521 (13)	0.2539 (16)	0.1178 (14)	0.071 (7)	0.38 (2)
H24B	−0.2355	0.1885	0.1405	0.085*	0.38 (2)
C25'	−0.2036 (11)	0.3438 (19)	0.1163 (18)	0.046 (7)	0.38 (2)
C26	−0.1136 (3)	0.3408 (4)	0.1505 (2)	0.0623 (12)
C27	−0.0547 (3)	0.4415 (4)	0.1619 (2)	0.0546 (11)
H27A	−0.0465	0.4663	0.2061	0.066*
H27B	−0.0825	0.5010	0.1337	0.066*
C28	0.0343 (2)	0.4160 (3)	0.14914 (19)	0.0482 (10)
H28A	0.0512	0.3412	0.1653	0.058*
C29	0.1076 (3)	0.4943 (3)	0.18146 (19)	0.0468 (10)
C30	0.1872 (3)	0.4509 (3)	0.2160 (2)	0.0538 (11)
H30A	0.1943	0.3750	0.2227	0.065*
C31	0.2547 (3)	0.5222 (3)	0.2398 (2)	0.0507 (11)
C32	0.2457 (3)	0.6340 (3)	0.2303 (2)	0.0527 (11)
C33	0.1686 (3)	0.6798 (4)	0.1986 (2)	0.0674 (14)
H33A	0.1623	0.7560	0.1934	0.081*
C34	0.0988 (3)	0.6077 (4)	0.1740 (2)	0.0613 (13)
H34A	0.0450	0.6369	0.1521	0.074*
C35	0.3864 (3)	0.5988 (4)	0.2786 (3)	0.0746 (15)
H35A	0.4276	0.5957	0.2515	0.090*
H35B	0.4192	0.6115	0.3228	0.090*
C36	0.1785 (3)	0.3269 (3)	0.06972 (19)	0.0470 (10)
C37	0.2235 (3)	0.2348 (4)	0.0972 (2)	0.0621 (13)
H37A	0.1936	0.1687	0.0985	0.075*
C38	0.3127 (3)	0.2401 (5)	0.1229 (3)	0.0765 (15)
H38A	0.3426	0.1770	0.1413	0.092*
C39	0.3582 (3)	0.3361 (5)	0.1218 (3)	0.0739 (15)
C40	0.3128 (3)	0.4275 (5)	0.0934 (3)	0.0761 (15)
H40A	0.3430	0.4931	0.0917	0.091*
C41	0.2225 (3)	0.4241 (4)	0.0672 (2)	0.0659 (13)
H41A	0.1924	0.4868	0.0484	0.079*
C42	0.4550 (3)	0.3430 (4)	0.1517 (3)	0.081
H42A	0.4843	0.2830	0.1362	0.122*
H42B	0.4655	0.3383	0.1978	0.122*
H42C	0.4771	0.4121	0.1402	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0518 (7)	0.0591 (7)	0.0506 (7)	0.0012 (6)	0.0010 (5)	−0.0112 (6)
N1	0.0387 (19)	0.068 (2)	0.052 (2)	0.0048 (17)	−0.0013 (17)	−0.0053 (19)
O2	0.069 (2)	0.078 (3)	0.128 (3)	−0.019 (2)	0.015 (2)	−0.017 (2)
O3	0.082 (2)	0.089 (2)	0.0483 (19)	0.0160 (19)	−0.0049 (17)	−0.0049 (17)
O4	0.070 (2)	0.057 (2)	0.088 (2)	−0.0084 (16)	0.0071 (18)	−0.0176 (17)
O5	0.062 (2)	0.0513 (19)	0.109 (3)	−0.0101 (17)	−0.0197 (19)	−0.0127 (19)
O6	0.0524 (19)	0.059 (2)	0.103 (3)	0.0012 (16)	−0.0153 (18)	−0.0102 (19)
O1	0.073 (3)	0.132 (3)	0.106 (3)	−0.036 (2)	0.014 (2)	−0.020 (3)
C1	0.063 (4)	0.184 (7)	0.105 (5)	−0.007 (5)	0.007 (3)	0.010 (5)
C2	0.080 (4)	0.155 (6)	0.124 (5)	0.022 (4)	0.023 (4)	0.045 (5)
C3	0.066 (3)	0.104 (4)	0.096 (4)	−0.012 (3)	0.015 (3)	0.011 (3)
C4	0.056 (3)	0.082 (3)	0.067 (3)	−0.027 (3)	0.012 (2)	−0.005 (3)
C5	0.052 (3)	0.082 (4)	0.069 (3)	−0.017 (3)	0.017 (3)	−0.010 (3)
C6	0.053 (3)	0.082 (3)	0.071 (3)	−0.024 (3)	0.014 (2)	−0.022 (3)
C7	0.045 (2)	0.059 (3)	0.051 (3)	−0.008 (2)	0.004 (2)	−0.007 (2)
C8	0.046 (2)	0.048 (2)	0.044 (2)	−0.0108 (19)	0.0095 (19)	−0.0029 (19)
C9	0.050 (3)	0.045 (2)	0.054 (3)	−0.002 (2)	0.006 (2)	0.000 (2)
C10	0.037 (2)	0.047 (2)	0.051 (3)	−0.003 (2)	0.000 (2)	0.000 (2)
C11	0.051 (3)	0.046 (3)	0.060 (3)	−0.013 (2)	−0.001 (2)	−0.002 (2)
C12	0.061 (3)	0.041 (2)	0.072 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
C13	0.047 (3)	0.054 (3)	0.057 (3)	0.001 (2)	−0.001 (2)	0.003 (2)
C14	0.055 (3)	0.069 (3)	0.132 (5)	−0.007 (3)	−0.017 (3)	−0.017 (3)
C15	0.050 (3)	0.057 (3)	0.046 (3)	−0.001 (2)	0.013 (2)	−0.004 (2)
C16	0.060 (3)	0.063 (3)	0.076 (3)	0.004 (3)	0.010 (3)	−0.016 (3)
C17	0.052 (3)	0.105 (5)	0.099 (4)	0.016 (3)	0.010 (3)	−0.025 (4)
C18	0.048 (3)	0.130 (6)	0.097 (4)	−0.018 (4)	0.022 (3)	−0.031 (4)
C19	0.083 (4)	0.090 (4)	0.108 (5)	−0.037 (4)	0.027 (4)	−0.003 (4)
C20	0.074 (4)	0.067 (3)	0.086 (4)	−0.006 (3)	0.016 (3)	0.015 (3)
C21	0.086	0.122	0.097	0.000	0.020	0.000
S2	0.0432 (6)	0.0563 (7)	0.0495 (7)	−0.0008 (5)	0.0005 (5)	−0.0080 (6)
N2	0.045 (2)	0.058 (2)	0.046 (2)	0.0084 (17)	−0.0006 (16)	−0.0001 (17)
O8	0.075 (2)	0.068 (2)	0.135 (4)	0.000 (2)	0.031 (2)	0.023 (2)
O9	0.073 (2)	0.086 (2)	0.0441 (18)	0.0145 (18)	−0.0008 (16)	−0.0082 (16)
O10	0.0532 (19)	0.0554 (19)	0.095 (3)	−0.0131 (15)	0.0048 (17)	−0.0109 (17)
O11	0.060 (2)	0.0510 (18)	0.091 (2)	−0.0031 (16)	−0.0071 (18)	−0.0098 (17)
O12	0.056 (2)	0.059 (2)	0.110 (3)	0.0061 (17)	−0.0208 (19)	0.0075 (19)
O7	0.081 (7)	0.086 (6)	0.094 (7)	−0.014 (5)	0.020 (5)	−0.001 (4)
C22	0.081 (7)	0.088 (9)	0.100 (8)	−0.040 (7)	0.020 (6)	−0.003 (7)
C23	0.073 (7)	0.101 (8)	0.097 (7)	0.020 (6)	0.005 (5)	0.011 (7)
C24	0.065 (7)	0.089 (9)	0.093 (9)	−0.013 (6)	0.005 (6)	−0.004 (7)
C25	0.060 (8)	0.069 (8)	0.076 (8)	−0.014 (6)	0.021 (6)	0.001 (7)
O7'	0.057 (8)	0.080 (8)	0.071 (8)	−0.010 (6)	0.005 (6)	0.004 (7)
C22'	0.060 (8)	0.056 (10)	0.072 (9)	0.005 (7)	0.009 (6)	0.009 (8)
C23'	0.052 (8)	0.070 (9)	0.084 (9)	−0.015 (7)	0.009 (7)	−0.003 (8)
C24'	0.052 (9)	0.081 (10)	0.076 (11)	−0.003 (7)	0.009 (7)	0.015 (7)
C25'	0.044 (10)	0.050 (8)	0.046 (9)	−0.011 (6)	0.015 (7)	−0.002 (7)
C26	0.056 (3)	0.070 (3)	0.065 (3)	−0.002 (3)	0.021 (2)	0.007 (3)
C27	0.051 (3)	0.059 (3)	0.054 (3)	−0.001 (2)	0.014 (2)	0.001 (2)
C28	0.045 (2)	0.050 (2)	0.047 (2)	0.000 (2)	0.005 (2)	0.004 (2)
C29	0.048 (2)	0.047 (3)	0.043 (2)	0.002 (2)	0.007 (2)	0.0027 (19)
C30	0.053 (3)	0.043 (2)	0.058 (3)	0.005 (2)	0.001 (2)	0.010 (2)
C31	0.046 (3)	0.051 (3)	0.048 (3)	0.005 (2)	−0.003 (2)	0.000 (2)
C32	0.051 (3)	0.045 (2)	0.056 (3)	−0.001 (2)	0.000 (2)	−0.007 (2)
C33	0.065 (3)	0.043 (2)	0.080 (3)	0.005 (2)	−0.008 (3)	−0.004 (2)
C34	0.053 (3)	0.053 (3)	0.067 (3)	0.011 (2)	−0.006 (2)	0.000 (2)
C35	0.058 (3)	0.059 (3)	0.095 (4)	0.005 (3)	−0.005 (3)	−0.005 (3)
C36	0.044 (2)	0.051 (2)	0.046 (2)	−0.002 (2)	0.0108 (19)	−0.004 (2)
C37	0.051 (3)	0.052 (3)	0.079 (3)	0.000 (2)	0.009 (2)	−0.006 (2)
C38	0.051 (3)	0.080 (4)	0.090 (4)	0.014 (3)	0.000 (3)	−0.006 (3)
C39	0.038 (3)	0.098 (4)	0.084 (4)	−0.002 (3)	0.011 (3)	−0.035 (3)
C40	0.066 (3)	0.077 (4)	0.091 (4)	−0.031 (3)	0.031 (3)	−0.023 (3)
C41	0.060 (3)	0.060 (3)	0.077 (3)	−0.008 (2)	0.017 (3)	−0.005 (3)
C42	0.065	0.087	0.086	0.000	0.007	0.000

Geometric parameters (Å, º)

S1—O4	1.419 (3)	N2—H2	0.8600
S1—O3	1.442 (3)	O8—C26	1.210 (5)
S1—N1	1.616 (4)	O11—C32	1.380 (5)
S1—C15	1.753 (4)	O11—C35	1.426 (5)
N1—C7	1.471 (5)	O12—C31	1.374 (5)
N1—H1	0.8600	O12—C35	1.418 (5)
O2—C5	1.209 (6)	O7—C22	1.412 (9)
O5—C11	1.375 (5)	O7—C25	1.417 (8)
O5—C14	1.411 (6)	C22—C23	1.327 (9)
O6—C10	1.371 (4)	C22—H22A	0.9300
O6—C14	1.434 (5)	C23—C24	1.488 (9)
O1—C1	1.369 (6)	C23—H23A	0.9300
O1—C4	1.388 (5)	C24—C25	1.338 (9)
C1—C2	1.312 (7)	C24—H24A	0.9300
C1—H1A	0.9300	C25—C26	1.479 (10)
C2—C3	1.465 (6)	O7'—C25'	1.411 (9)
C2—H2A	0.9300	O7'—C22'	1.422 (9)
C3—C4	1.332 (6)	C22'—C23'	1.340 (9)
C3—H3A	0.9300	C22'—H22B	0.9300
C4—C5	1.438 (7)	C23'—C24'	1.484 (10)
C5—C6	1.515 (6)	C23'—H23B	0.9300
C6—C7	1.529 (6)	C24'—C25'	1.333 (9)
C6—H6A	0.9700	C24'—H24B	0.9300
C6—H6B	0.9700	C25'—C26	1.422 (12)
C7—C8	1.519 (5)	C26—C27	1.512 (6)
C7—H7A	0.9800	C27—C28	1.522 (5)
C8—C9	1.384 (5)	C27—H27A	0.9700
C8—C13	1.390 (6)	C27—H27B	0.9700
C9—C10	1.353 (5)	C28—C29	1.519 (5)
C9—H9A	0.9300	C28—H28A	0.9800
C10—C11	1.367 (6)	C29—C34	1.382 (6)
C11—C12	1.361 (6)	C29—C30	1.388 (5)
C12—C13	1.400 (6)	C30—C31	1.364 (6)
C12—H12A	0.9300	C30—H30A	0.9300
C13—H13A	0.9300	C31—C32	1.368 (6)
C14—H14A	0.9700	C32—C33	1.352 (6)
C14—H14B	0.9700	C33—C34	1.397 (6)
C15—C16	1.375 (6)	C33—H33A	0.9300
C15—C20	1.376 (6)	C34—H34A	0.9300
C16—C17	1.377 (7)	C35—H35A	0.9700
C16—H16A	0.9300	C35—H35B	0.9700
C17—C18	1.350 (8)	C36—C41	1.370 (6)
C17—H17A	0.9300	C36—C37	1.370 (6)
C18—C19	1.381 (8)	C37—C38	1.375 (6)
C18—C21	1.508 (7)	C37—H37A	0.9300
C19—C20	1.384 (7)	C38—C39	1.367 (7)
C19—H19A	0.9300	C38—H38A	0.9300
C20—H20A	0.9300	C39—C40	1.372 (7)
C21—H21A	0.9600	C39—C42	1.499 (6)
C21—H21B	0.9600	C40—C41	1.392 (6)
C21—H21C	0.9600	C40—H40A	0.9300
S2—O10	1.419 (3)	C41—H41A	0.9300
S2—O9	1.432 (3)	C42—H42A	0.9600
S2—N2	1.613 (3)	C42—H42B	0.9600
S2—C36	1.754 (4)	C42—H42C	0.9600
N2—C28	1.470 (5)
O4—S1—O3	118.6 (2)	C22—O7—C25	100.0 (7)
O4—S1—N1	109.5 (2)	C23—C22—O7	115.2 (8)
O3—S1—N1	104.17 (19)	C23—C22—H22A	122.4
O4—S1—C15	107.6 (2)	O7—C22—H22A	122.4
O3—S1—C15	108.8 (2)	C22—C23—C24	105.4 (7)
N1—S1—C15	107.64 (18)	C22—C23—H23A	127.3
C7—N1—S1	120.9 (3)	C24—C23—H23A	127.3
C7—N1—H1	119.5	C25—C24—C23	104.1 (7)
S1—N1—H1	119.5	C25—C24—H24A	128.0
C11—O5—C14	105.4 (3)	C23—C24—H24A	128.0
C10—O6—C14	105.0 (3)	C24—C25—O7	115.3 (8)
C1—O1—C4	104.2 (5)	C24—C25—C26	126.6 (11)
C2—C1—O1	113.3 (6)	O7—C25—C26	117.9 (11)
C2—C1—H1A	123.3	C25'—O7'—C22'	99.8 (9)
O1—C1—H1A	123.3	C23'—C22'—O7'	114.2 (10)
C1—C2—C3	105.3 (5)	C23'—C22'—H22B	122.9
C1—C2—H2A	127.4	O7'—C22'—H22B	122.9
C3—C2—H2A	127.4	C22'—C23'—C24'	105.8 (8)
C4—C3—C2	105.9 (5)	C22'—C23'—H23B	127.1
C4—C3—H3A	127.0	C24'—C23'—H23B	127.1
C2—C3—H3A	127.0	C25'—C24'—C23'	103.8 (7)
C3—C4—O1	111.3 (4)	C25'—C24'—H24B	128.1
C3—C4—C5	133.1 (5)	C23'—C24'—H24B	128.1
O1—C4—C5	115.6 (5)	C24'—C25'—O7'	116.2 (9)
O2—C5—C4	123.4 (5)	C24'—C25'—C26	117.9 (14)
O2—C5—C6	119.8 (5)	O7'—C25'—C26	125.8 (13)
C4—C5—C6	116.8 (5)	O8—C26—C25'	116.1 (9)
C5—C6—C7	110.7 (4)	O8—C26—C25	126.0 (7)
C5—C6—H6A	109.5	C25'—C26—C25	10.0 (12)
C7—C6—H6A	109.5	O8—C26—C27	120.3 (4)
C5—C6—H6B	109.5	C25'—C26—C27	123.6 (9)
C7—C6—H6B	109.5	C25—C26—C27	113.7 (6)
H6A—C6—H6B	108.1	C26—C27—C28	111.2 (4)
N1—C7—C8	112.4 (3)	C26—C27—H27A	109.4
N1—C7—C6	109.2 (3)	C28—C27—H27A	109.4
C8—C7—C6	112.8 (3)	C26—C27—H27B	109.4
N1—C7—H7A	107.4	C28—C27—H27B	109.4
C8—C7—H7A	107.4	H27A—C27—H27B	108.0
C6—C7—H7A	107.4	N2—C28—C29	111.4 (3)
C9—C8—C13	119.5 (4)	N2—C28—C27	107.0 (3)
C9—C8—C7	119.4 (4)	C29—C28—C27	114.8 (3)
C13—C8—C7	121.1 (4)	N2—C28—H28A	107.8
C10—C9—C8	118.6 (4)	C29—C28—H28A	107.8
C10—C9—H9A	120.7	C27—C28—H28A	107.8
C8—C9—H9A	120.7	C34—C29—C30	119.2 (4)
C9—C10—C11	121.8 (4)	C34—C29—C28	121.5 (4)
C9—C10—O6	128.3 (4)	C30—C29—C28	119.2 (4)
C11—C10—O6	109.9 (3)	C31—C30—C29	118.4 (4)
C12—C11—C10	122.1 (4)	C31—C30—H30A	120.8
C12—C11—O5	128.3 (4)	C29—C30—H30A	120.8
C10—C11—O5	109.7 (4)	C30—C31—C32	121.7 (4)
C11—C12—C13	116.6 (4)	C30—C31—O12	128.6 (4)
C11—C12—H12A	121.7	C32—C31—O12	109.7 (4)
C13—C12—H12A	121.7	C33—C32—C31	121.7 (4)
C8—C13—C12	121.5 (4)	C33—C32—O11	128.7 (4)
C8—C13—H13A	119.3	C31—C32—O11	109.5 (4)
C12—C13—H13A	119.3	C32—C33—C34	117.2 (4)
O5—C14—O6	107.6 (4)	C32—C33—H33A	121.4
O5—C14—H14A	110.2	C34—C33—H33A	121.4
O6—C14—H14A	110.2	C29—C34—C33	121.8 (4)
O5—C14—H14B	110.2	C29—C34—H34A	119.1
O6—C14—H14B	110.2	C33—C34—H34A	119.1
H14A—C14—H14B	108.5	O12—C35—O11	107.5 (3)
C16—C15—C20	119.8 (4)	O12—C35—H35A	110.2
C16—C15—S1	119.9 (3)	O11—C35—H35A	110.2
C20—C15—S1	120.3 (4)	O12—C35—H35B	110.2
C15—C16—C17	119.7 (5)	O11—C35—H35B	110.2
C15—C16—H16A	120.1	H35A—C35—H35B	108.5
C17—C16—H16A	120.1	C41—C36—C37	120.1 (4)
C18—C17—C16	121.7 (5)	C41—C36—S2	119.5 (3)
C18—C17—H17A	119.2	C37—C36—S2	120.3 (3)
C16—C17—H17A	119.2	C36—C37—C38	120.0 (4)
C17—C18—C19	118.5 (5)	C36—C37—H37A	120.0
C17—C18—C21	121.6 (6)	C38—C37—H37A	120.0
C19—C18—C21	119.9 (6)	C39—C38—C37	121.3 (5)
C18—C19—C20	121.2 (5)	C39—C38—H38A	119.4
C18—C19—H19A	119.4	C37—C38—H38A	119.4
C20—C19—H19A	119.4	C38—C39—C40	118.2 (4)
C15—C20—C19	119.1 (5)	C38—C39—C42	121.4 (5)
C15—C20—H20A	120.4	C40—C39—C42	120.4 (5)
C19—C20—H20A	120.4	C39—C40—C41	121.5 (5)
O10—S2—O9	119.0 (2)	C39—C40—H40A	119.2
O10—S2—N2	109.0 (2)	C41—C40—H40A	119.2
O9—S2—N2	103.61 (18)	C36—C41—C40	118.9 (5)
O10—S2—C36	107.14 (19)	C36—C41—H41A	120.6
O9—S2—C36	109.5 (2)	C40—C41—H41A	120.6
N2—S2—C36	108.22 (18)	C39—C42—H42A	109.5
C28—N2—S2	124.2 (3)	C39—C42—H42B	109.5
C28—N2—H2	117.9	H42A—C42—H42B	109.5
S2—N2—H2	117.9	C39—C42—H42C	109.5
C32—O11—C35	105.8 (3)	H42A—C42—H42C	109.5
C31—O12—C35	106.2 (3)	H42B—C42—H42C	109.5
O4—S1—N1—C7	57.8 (3)	C23—C24—C25—C26	−178 (3)
O3—S1—N1—C7	−174.4 (3)	C22—O7—C25—C24	3 (3)
C15—S1—N1—C7	−58.9 (4)	C22—O7—C25—C26	178 (2)
C4—O1—C1—C2	−1.0 (8)	C25'—O7'—C22'—C23'	4 (3)
O1—C1—C2—C3	0.4 (9)	O7'—C22'—C23'—C24'	−2 (3)
C1—C2—C3—C4	0.4 (8)	C22'—C23'—C24'—C25'	−1 (4)
C2—C3—C4—O1	−1.1 (7)	C23'—C24'—C25'—O7'	4 (4)
C2—C3—C4—C5	−179.9 (6)	C23'—C24'—C25'—C26	−176 (3)
C1—O1—C4—C3	1.3 (6)	C22'—O7'—C25'—C24'	−5 (4)
C1—O1—C4—C5	−179.7 (5)	C22'—O7'—C25'—C26	176 (3)
C3—C4—C5—O2	177.0 (6)	C24'—C25'—C26—O8	8 (4)
O1—C4—C5—O2	−1.8 (8)	O7'—C25'—C26—O8	−172 (3)
C3—C4—C5—C6	−1.1 (9)	O7'—C25'—C26—C25	1 (15)
O1—C4—C5—C6	−179.9 (4)	C24'—C25'—C26—C27	−170 (3)
O2—C5—C6—C7	55.3 (7)	O7'—C25'—C26—C27	10 (5)
C4—C5—C6—C7	−126.4 (5)	C24—C25—C26—O8	178 (2)
S1—N1—C7—C8	93.6 (4)	O7—C25—C26—O8	4 (3)
S1—N1—C7—C6	−140.5 (3)	O7—C25—C26—C25'	−5 (16)
C5—C6—C7—N1	60.9 (5)	C24—C25—C26—C27	−2 (4)
C5—C6—C7—C8	−173.5 (4)	O7—C25—C26—C27	−176.4 (19)
N1—C7—C8—C9	−115.6 (4)	O8—C26—C27—C28	46.4 (6)
C6—C7—C8—C9	120.5 (4)	C25'—C26—C27—C28	−135 (2)
N1—C7—C8—C13	64.5 (5)	C25—C26—C27—C28	−133.7 (16)
C6—C7—C8—C13	−59.4 (6)	S2—N2—C28—C29	96.9 (4)
C13—C8—C9—C10	−1.1 (6)	S2—N2—C28—C27	−136.7 (3)
C7—C8—C9—C10	179.0 (4)	C26—C27—C28—N2	77.1 (4)
C8—C9—C10—C11	2.2 (7)	C26—C27—C28—C29	−158.7 (4)
C8—C9—C10—O6	−179.0 (4)	N2—C28—C29—C34	69.3 (5)
C14—O6—C10—C9	173.0 (5)	C27—C28—C29—C34	−52.6 (6)
C14—O6—C10—C11	−8.1 (5)	N2—C28—C29—C30	−106.8 (4)
C9—C10—C11—C12	−2.4 (7)	C27—C28—C29—C30	131.4 (4)
O6—C10—C11—C12	178.6 (4)	C34—C29—C30—C31	−1.9 (7)
C9—C10—C11—O5	177.6 (4)	C28—C29—C30—C31	174.3 (4)
O6—C10—C11—O5	−1.5 (5)	C29—C30—C31—C32	−0.1 (7)
C14—O5—C11—C12	−169.6 (5)	C29—C30—C31—O12	−178.9 (4)
C14—O5—C11—C10	10.5 (6)	C35—O12—C31—C30	171.2 (5)
C10—C11—C12—C13	1.3 (7)	C35—O12—C31—C32	−7.7 (5)
O5—C11—C12—C13	−178.6 (5)	C30—C31—C32—C33	2.1 (8)
C9—C8—C13—C12	0.1 (7)	O12—C31—C32—C33	−179.0 (4)
C7—C8—C13—C12	−180.0 (4)	C30—C31—C32—O11	−178.2 (4)
C11—C12—C13—C8	−0.2 (7)	O12—C31—C32—O11	0.8 (5)
C11—O5—C14—O6	−15.3 (6)	C35—O11—C32—C33	−173.9 (5)
C10—O6—C14—O5	14.5 (6)	C35—O11—C32—C31	6.4 (5)
O4—S1—C15—C16	−2.6 (4)	C31—C32—C33—C34	−1.9 (8)
O3—S1—C15—C16	−132.3 (4)	O11—C32—C33—C34	178.4 (4)
N1—S1—C15—C16	115.4 (4)	C30—C29—C34—C33	2.0 (7)
O4—S1—C15—C20	−179.3 (4)	C28—C29—C34—C33	−174.0 (4)
O3—S1—C15—C20	51.0 (4)	C32—C33—C34—C29	−0.1 (8)
N1—S1—C15—C20	−61.4 (4)	C31—O12—C35—O11	11.5 (5)
C20—C15—C16—C17	−0.3 (7)	C32—O11—C35—O12	−11.0 (5)
S1—C15—C16—C17	−177.1 (4)	O10—S2—C36—C41	−174.5 (4)
C15—C16—C17—C18	0.3 (9)	O9—S2—C36—C41	55.2 (4)
C16—C17—C18—C19	0.4 (9)	N2—S2—C36—C41	−57.1 (4)
C16—C17—C18—C21	179.9 (5)	O10—S2—C36—C37	3.0 (4)
C17—C18—C19—C20	−1.0 (9)	O9—S2—C36—C37	−127.3 (4)
C21—C18—C19—C20	179.4 (5)	N2—S2—C36—C37	120.4 (4)
C16—C15—C20—C19	−0.3 (8)	C41—C36—C37—C38	0.6 (7)
S1—C15—C20—C19	176.5 (4)	S2—C36—C37—C38	−176.9 (4)
C18—C19—C20—C15	0.9 (9)	C36—C37—C38—C39	0.1 (8)
O10—S2—N2—C28	57.2 (3)	C37—C38—C39—C40	−0.9 (8)
O9—S2—N2—C28	−175.2 (3)	C37—C38—C39—C42	178.0 (5)
C36—S2—N2—C28	−59.0 (4)	C38—C39—C40—C41	1.0 (8)
C25—O7—C22—C23	−1 (2)	C42—C39—C40—C41	−177.9 (5)
O7—C22—C23—C24	0 (2)	C37—C36—C41—C40	−0.5 (7)
C22—C23—C24—C25	2 (3)	S2—C36—C41—C40	177.0 (4)
C23—C24—C25—O7	−3 (3)	C39—C40—C41—C36	−0.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	2.26	2.957 (5)	138
N2—H2···O9^ii	0.86	2.21	3.012 (5)	155

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