(E)-1-[3-Meth­oxy-4-(p-tolyl­sulfon­yloxy)benzyl­idene]-2-(4-nitro­phen­yl)hydrazine

The title compound, C₂₁H₁₉N₃O₆S, crystallizes with two mol­ecules in the asymmetric unit. The conformations of these non-planar mol­ecules are similar. Inter­molecular N—H...O and C—H...O hydrogen bonds help to consolidate the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.086
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C18    -   C19     ..       7.65 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O6      ..       5.15 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C21     ..       6.46 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C27     ..       5.32 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C39
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C28     ..       2.94 Ang.

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           26.47
           From the CIF: _reflns_number_total               8350
           Count of symmetry unique reflns         4491
           Completeness (_total/calc)            185.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3859
           Fraction of Friedel pairs measured     0.859
           Are heavy atom types Z>Si present        yes

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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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.

(E)-1-[3-Methoxy-4-(p-tolylsulfonyloxy)benzylidene]-2-(4-nitrophenyl)hydrazine

Crystal data

C21H19N3O6S	F(000) = 1840
Mr = 441.45	Dx = 1.414 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2694 reflections
a = 20.272 (3) Å	θ = 2.3–20.6°
b = 16.568 (3) Å	µ = 0.20 mm^−1
c = 12.348 (2) Å	T = 294 K
V = 4147.3 (12) Å^3	Block, yellow
Z = 8	0.22 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer	8350 independent reflections
Radiation source: fine-focus sealed tube	3462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ω scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.945, Tmax = 0.961	k = −20→14
22718 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0156P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
8350 reflections	Δρmax = 0.33 e Å^−3
562 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: Flack (1983), 3859 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (8)

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 > 2σ(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	0.08491 (6)	0.62284 (10)	0.25868 (13)	0.0687 (4)
S2	1.14695 (6)	0.11899 (8)	0.33562 (12)	0.0607 (4)
O1	0.3382 (2)	1.3506 (2)	0.1193 (4)	0.1108 (17)
O2	0.4432 (2)	1.3512 (2)	0.1175 (4)	0.129 (2)
O3	0.24144 (14)	0.59340 (19)	0.1421 (3)	0.0692 (10)
O4	0.12097 (14)	0.65884 (17)	0.1541 (2)	0.0593 (9)
O5	0.08757 (15)	0.6797 (2)	0.3442 (3)	0.0813 (11)
O6	0.02315 (14)	0.5981 (2)	0.2157 (3)	0.0941 (13)
O7	0.7987 (2)	0.8603 (2)	0.4747 (4)	0.1137 (17)
O8	0.9043 (2)	0.8573 (2)	0.4674 (4)	0.1035 (17)
O9	0.98419 (13)	0.09614 (18)	0.4252 (3)	0.0603 (9)
O10	1.10797 (13)	0.15456 (17)	0.4389 (3)	0.0552 (9)
O11	1.14690 (15)	0.1775 (2)	0.2508 (3)	0.0784 (11)
O12	1.20773 (13)	0.09187 (18)	0.3842 (3)	0.0808 (12)
N1	0.3902 (3)	1.3146 (3)	0.1231 (4)	0.0768 (15)
N2	0.39454 (17)	0.9804 (2)	0.1646 (3)	0.0577 (11)
H2	0.4320	0.9563	0.1693	0.069*
N3	0.33796 (18)	0.9373 (2)	0.1661 (3)	0.0498 (11)
N4	0.8509 (3)	0.8236 (3)	0.4655 (4)	0.0794 (17)
N5	0.84333 (16)	0.4892 (2)	0.4280 (3)	0.0542 (10)
H5	0.8057	0.4654	0.4232	0.065*
N6	0.89973 (16)	0.4442 (2)	0.4268 (3)	0.0505 (10)
C1	0.3912 (3)	1.2281 (3)	0.1364 (4)	0.0562 (15)
C2	0.3326 (2)	1.1864 (3)	0.1429 (4)	0.0571 (14)
H2A	0.2928	1.2142	0.1397	0.068*
C3	0.3324 (2)	1.1055 (3)	0.1539 (4)	0.0514 (13)
H3	0.2927	1.0778	0.1603	0.062*
C4	0.3919 (2)	1.0635 (3)	0.1556 (4)	0.0488 (13)
C5	0.4515 (2)	1.1072 (3)	0.1492 (4)	0.0584 (15)
H5A	0.4918	1.0805	0.1521	0.070*
C6	0.4495 (3)	1.1878 (3)	0.1391 (4)	0.0691 (16)
H6	0.4888	1.2166	0.1337	0.083*
C7	0.3438 (2)	0.8598 (3)	0.1696 (4)	0.0516 (13)
H7	0.3854	0.8363	0.1720	0.062*
C8	0.2855 (2)	0.8096 (3)	0.1700 (4)	0.0440 (14)
C9	0.2219 (2)	0.8392 (3)	0.1774 (4)	0.0568 (15)
H9	0.2158	0.8945	0.1849	0.068*
C10	0.1686 (2)	0.7910 (3)	0.1741 (4)	0.0567 (15)
H10	0.1264	0.8128	0.1777	0.068*
C11	0.1777 (3)	0.7084 (3)	0.1654 (4)	0.0488 (14)
C12	0.2391 (3)	0.6750 (3)	0.1577 (4)	0.0493 (14)
C13	0.2932 (2)	0.7244 (3)	0.1602 (4)	0.0535 (14)
H13	0.3352	0.7022	0.1555	0.064*
C14	0.3033 (2)	0.5538 (3)	0.1601 (4)	0.0813 (18)
H14A	0.3360	0.5760	0.1124	0.122*
H14B	0.2986	0.4971	0.1460	0.122*
H14C	0.3167	0.5617	0.2339	0.122*
C15	0.1322 (2)	0.5368 (3)	0.2921 (5)	0.0544 (14)
C16	0.1301 (2)	0.4714 (3)	0.2237 (4)	0.0669 (16)
H16	0.1029	0.4719	0.1631	0.080*
C17	0.1690 (2)	0.4050 (3)	0.2459 (5)	0.0677 (15)
H17	0.1691	0.3614	0.1984	0.081*
C18	0.2074 (3)	0.4026 (3)	0.3374 (5)	0.0580 (15)
C19	0.2096 (2)	0.4695 (4)	0.4032 (4)	0.0723 (17)
H19	0.2377	0.4696	0.4626	0.087*
C20	0.1706 (2)	0.5375 (3)	0.3831 (4)	0.0667 (16)
H20	0.1707	0.5815	0.4298	0.080*
C21	0.2507 (2)	0.3333 (3)	0.3632 (4)	0.0829 (17)
H21A	0.2903	0.3367	0.3209	0.124*
H21B	0.2281	0.2839	0.3468	0.124*
H21C	0.2618	0.3344	0.4388	0.124*
C22	0.8488 (3)	0.7369 (3)	0.4574 (4)	0.0518 (14)
C23	0.7890 (2)	0.6966 (3)	0.4534 (4)	0.0595 (15)
H23	0.7497	0.7255	0.4580	0.071*
C24	0.7877 (2)	0.6154 (3)	0.4430 (4)	0.0598 (14)
H24	0.7473	0.5888	0.4399	0.072*
C25	0.8457 (2)	0.5712 (3)	0.4367 (4)	0.0451 (12)
C26	0.9059 (2)	0.6129 (3)	0.4399 (4)	0.0557 (14)
H26	0.9454	0.5845	0.4353	0.067*
C27	0.9067 (2)	0.6948 (3)	0.4498 (4)	0.0580 (15)
H27	0.9467	0.7222	0.4513	0.070*
C28	0.89281 (19)	0.3685 (3)	0.4196 (4)	0.0507 (12)
H28	0.8506	0.3472	0.4133	0.061*
C29	0.9495 (2)	0.3134 (3)	0.4211 (4)	0.0434 (13)
C30	1.0145 (2)	0.3430 (3)	0.4248 (4)	0.0550 (15)
H30	1.0225	0.3982	0.4257	0.066*
C31	1.0663 (2)	0.2893 (3)	0.4271 (4)	0.0534 (14)
H31	1.1094	0.3084	0.4293	0.064*
C32	1.0545 (2)	0.2077 (3)	0.4261 (4)	0.0466 (13)
C33	0.9905 (2)	0.1777 (3)	0.4232 (4)	0.0435 (13)
C34	0.9396 (2)	0.2320 (3)	0.4205 (4)	0.0472 (13)
H34	0.8965	0.2126	0.4181	0.057*
C35	0.9201 (2)	0.0623 (3)	0.4110 (5)	0.0762 (19)
H35A	0.8919	0.0798	0.4688	0.114*
H35B	0.9231	0.0045	0.4116	0.114*
H35C	0.9022	0.0798	0.3430	0.114*
C36	1.1003 (2)	0.0348 (3)	0.2986 (4)	0.0508 (13)
C37	1.0969 (2)	−0.0308 (3)	0.3647 (4)	0.0574 (14)
H37	1.1214	−0.0320	0.4284	0.069*
C38	1.0573 (2)	−0.0957 (3)	0.3379 (5)	0.0635 (14)
H38	1.0561	−0.1408	0.3827	0.076*
C39	1.0197 (2)	−0.0939 (3)	0.2456 (5)	0.0538 (13)
C40	1.0229 (2)	−0.0269 (3)	0.1807 (4)	0.0661 (15)
H40	0.9978	−0.0252	0.1177	0.079*
C41	1.0628 (2)	0.0384 (3)	0.2063 (4)	0.0610 (14)
H41	1.0641	0.0837	0.1618	0.073*
C42	0.9753 (2)	−0.1651 (3)	0.2174 (5)	0.0819 (17)
H42A	0.9986	−0.2015	0.1706	0.123*
H42B	0.9364	−0.1459	0.1814	0.123*
H42C	0.9629	−0.1929	0.2826	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0511 (9)	0.0824 (11)	0.0727 (10)	−0.0057 (9)	0.0115 (8)	−0.0022 (10)
S2	0.0448 (8)	0.0611 (9)	0.0762 (10)	0.0022 (7)	0.0062 (8)	−0.0077 (9)
O1	0.119 (4)	0.062 (3)	0.152 (5)	0.013 (3)	−0.009 (3)	0.015 (3)
O2	0.128 (4)	0.080 (3)	0.178 (5)	−0.049 (3)	−0.015 (3)	0.029 (3)
O3	0.058 (2)	0.050 (2)	0.099 (3)	0.0020 (18)	0.0204 (19)	−0.003 (2)
O4	0.0468 (17)	0.075 (2)	0.056 (2)	−0.0022 (18)	0.0016 (18)	0.0007 (19)
O5	0.098 (3)	0.077 (3)	0.069 (2)	0.006 (2)	0.026 (2)	−0.012 (3)
O6	0.040 (2)	0.121 (3)	0.121 (3)	−0.021 (2)	0.000 (2)	−0.004 (3)
O7	0.108 (4)	0.064 (3)	0.168 (5)	0.022 (3)	−0.006 (3)	−0.012 (3)
O8	0.125 (4)	0.060 (3)	0.125 (4)	−0.034 (3)	0.017 (3)	−0.014 (3)
O9	0.0449 (19)	0.045 (2)	0.091 (2)	0.0024 (15)	0.0058 (19)	0.007 (2)
O10	0.0419 (18)	0.063 (2)	0.060 (2)	0.0139 (16)	−0.0044 (19)	−0.0098 (19)
O11	0.084 (3)	0.074 (3)	0.076 (3)	−0.0092 (19)	0.023 (2)	0.011 (2)
O12	0.039 (2)	0.078 (3)	0.125 (3)	0.0121 (18)	−0.015 (2)	−0.023 (2)
N1	0.095 (5)	0.060 (4)	0.076 (4)	−0.012 (3)	−0.015 (3)	0.000 (3)
N2	0.044 (2)	0.048 (3)	0.081 (3)	0.006 (2)	−0.005 (2)	0.001 (2)
N3	0.046 (3)	0.050 (3)	0.054 (3)	−0.002 (2)	0.001 (2)	0.003 (3)
N4	0.112 (5)	0.044 (4)	0.082 (4)	0.009 (3)	0.010 (4)	−0.003 (3)
N5	0.039 (2)	0.044 (2)	0.080 (3)	−0.0003 (19)	0.001 (2)	0.003 (2)
N6	0.049 (2)	0.038 (2)	0.065 (3)	0.005 (2)	0.002 (2)	0.004 (2)
C1	0.062 (4)	0.055 (4)	0.052 (4)	−0.006 (3)	−0.006 (3)	0.004 (3)
C2	0.063 (4)	0.053 (4)	0.056 (4)	0.005 (3)	−0.003 (3)	−0.002 (3)
C3	0.049 (3)	0.046 (3)	0.059 (3)	0.002 (3)	−0.003 (3)	−0.005 (3)
C4	0.049 (3)	0.046 (3)	0.051 (3)	−0.004 (3)	−0.007 (3)	0.004 (3)
C5	0.038 (3)	0.062 (4)	0.076 (4)	0.002 (3)	−0.001 (3)	−0.007 (3)
C6	0.072 (4)	0.065 (4)	0.070 (4)	−0.022 (3)	0.006 (3)	0.009 (4)
C7	0.046 (3)	0.054 (3)	0.055 (3)	0.000 (3)	−0.004 (2)	−0.008 (3)
C8	0.044 (3)	0.042 (3)	0.046 (4)	0.001 (3)	−0.005 (3)	−0.002 (3)
C9	0.057 (4)	0.049 (3)	0.064 (4)	0.017 (3)	0.001 (3)	−0.004 (3)
C10	0.030 (3)	0.071 (4)	0.069 (4)	0.006 (3)	0.000 (3)	−0.008 (3)
C11	0.038 (3)	0.058 (4)	0.050 (4)	−0.006 (3)	0.002 (3)	−0.004 (3)
C12	0.050 (4)	0.039 (3)	0.058 (4)	−0.006 (3)	0.002 (3)	−0.007 (3)
C13	0.040 (3)	0.054 (3)	0.067 (4)	0.010 (3)	0.008 (3)	0.001 (3)
C14	0.073 (4)	0.052 (3)	0.119 (5)	0.017 (3)	0.030 (4)	0.001 (4)
C15	0.041 (3)	0.065 (4)	0.058 (4)	−0.009 (3)	0.004 (3)	−0.006 (3)
C16	0.061 (4)	0.079 (4)	0.061 (4)	−0.015 (3)	−0.005 (3)	−0.005 (4)
C17	0.061 (4)	0.078 (4)	0.064 (4)	−0.017 (3)	0.009 (3)	−0.003 (4)
C18	0.080 (4)	0.049 (4)	0.045 (4)	0.001 (3)	0.010 (3)	0.006 (4)
C19	0.060 (4)	0.099 (5)	0.058 (4)	−0.011 (3)	−0.010 (3)	0.016 (4)
C20	0.076 (4)	0.075 (4)	0.049 (4)	−0.010 (3)	0.005 (3)	−0.010 (3)
C21	0.061 (3)	0.099 (4)	0.088 (4)	−0.010 (3)	0.014 (3)	0.011 (4)
C22	0.063 (3)	0.040 (3)	0.053 (4)	0.006 (3)	0.002 (3)	0.001 (3)
C23	0.053 (4)	0.053 (4)	0.073 (4)	0.004 (3)	0.009 (3)	−0.002 (3)
C24	0.039 (3)	0.059 (3)	0.081 (4)	0.005 (3)	0.009 (3)	0.003 (4)
C25	0.048 (3)	0.039 (3)	0.048 (3)	−0.003 (2)	0.002 (3)	0.008 (3)
C26	0.034 (3)	0.069 (4)	0.064 (4)	0.006 (3)	0.003 (3)	0.008 (3)
C27	0.062 (4)	0.043 (3)	0.068 (4)	−0.013 (3)	−0.010 (3)	0.000 (3)
C28	0.047 (3)	0.052 (3)	0.053 (3)	−0.002 (2)	0.000 (2)	−0.001 (3)
C29	0.043 (3)	0.037 (3)	0.050 (3)	0.001 (2)	0.003 (3)	−0.002 (3)
C30	0.043 (3)	0.051 (3)	0.071 (4)	0.000 (3)	0.010 (3)	−0.001 (3)
C31	0.049 (3)	0.053 (3)	0.058 (4)	−0.015 (3)	0.002 (3)	−0.005 (3)
C32	0.039 (3)	0.054 (3)	0.047 (3)	0.003 (3)	−0.004 (3)	0.004 (3)
C33	0.048 (3)	0.034 (3)	0.049 (3)	−0.006 (3)	0.008 (3)	0.002 (3)
C34	0.035 (3)	0.052 (3)	0.055 (4)	−0.002 (2)	0.003 (2)	−0.001 (3)
C35	0.059 (3)	0.042 (3)	0.128 (6)	−0.004 (3)	−0.003 (4)	−0.002 (4)
C36	0.043 (3)	0.054 (3)	0.055 (3)	0.000 (3)	−0.001 (3)	−0.005 (3)
C37	0.054 (3)	0.055 (3)	0.063 (4)	0.008 (3)	−0.012 (3)	0.000 (3)
C38	0.059 (3)	0.058 (4)	0.073 (4)	0.001 (3)	−0.007 (3)	0.010 (4)
C39	0.046 (3)	0.050 (4)	0.066 (4)	0.006 (3)	0.001 (3)	−0.006 (3)
C40	0.057 (3)	0.085 (4)	0.056 (4)	0.009 (3)	−0.014 (3)	−0.010 (4)
C41	0.061 (3)	0.065 (4)	0.057 (4)	0.000 (3)	−0.008 (3)	0.008 (3)
C42	0.067 (4)	0.084 (4)	0.095 (5)	−0.003 (3)	−0.006 (3)	−0.023 (4)

Geometric parameters (Å, º)

S1—O5	1.415 (3)	C15—C20	1.366 (6)
S1—O6	1.420 (3)	C15—C16	1.375 (6)
S1—O4	1.600 (3)	C16—C17	1.381 (6)
S1—C15	1.767 (5)	C16—H16	0.9300
S2—O11	1.427 (3)	C17—C18	1.374 (7)
S2—O12	1.442 (3)	C17—H17	0.9300
S2—O10	1.612 (3)	C18—C19	1.374 (6)
S2—C36	1.746 (5)	C18—C21	1.480 (6)
O1—N1	1.213 (5)	C19—C20	1.398 (6)
O2—N1	1.235 (5)	C19—H19	0.9300
O3—C12	1.366 (5)	C20—H20	0.9300
O3—C14	1.432 (4)	C21—H21A	0.9600
O4—C11	1.419 (5)	C21—H21B	0.9600
O7—N4	1.226 (5)	C21—H21C	0.9600
O8—N4	1.219 (5)	C22—C27	1.367 (6)
O9—C33	1.357 (5)	C22—C23	1.385 (5)
O9—C35	1.426 (4)	C23—C24	1.352 (6)
O10—C32	1.406 (5)	C23—H23	0.9300
N1—C1	1.443 (6)	C24—C25	1.387 (5)
N2—N3	1.351 (4)	C24—H24	0.9300
N2—C4	1.381 (5)	C25—C26	1.404 (5)
N2—H2	0.8600	C26—C27	1.363 (6)
N3—C7	1.291 (5)	C26—H26	0.9300
N4—C22	1.440 (6)	C27—H27	0.9300
N5—C25	1.364 (5)	C28—C29	1.469 (5)
N5—N6	1.365 (4)	C28—H28	0.9300
N5—H5	0.8600	C29—C34	1.364 (5)
N6—C28	1.265 (5)	C29—C30	1.407 (5)
C1—C6	1.357 (6)	C30—C31	1.375 (5)
C1—C2	1.378 (6)	C30—H30	0.9300
C2—C3	1.346 (5)	C31—C32	1.373 (6)
C2—H2A	0.9300	C31—H31	0.9300
C3—C4	1.392 (5)	C32—C33	1.390 (5)
C3—H3	0.9300	C33—C34	1.370 (5)
C4—C5	1.411 (5)	C34—H34	0.9300
C5—C6	1.341 (6)	C35—H35A	0.9600
C5—H5A	0.9300	C35—H35B	0.9600
C6—H6	0.9300	C35—H35C	0.9600
C7—C8	1.446 (5)	C36—C37	1.361 (5)
C7—H7	0.9300	C36—C41	1.371 (5)
C8—C9	1.381 (5)	C37—C38	1.383 (5)
C8—C13	1.425 (6)	C37—H37	0.9300
C9—C10	1.344 (5)	C38—C39	1.371 (6)
C9—H9	0.9300	C38—H38	0.9300
C10—C11	1.386 (6)	C39—C40	1.371 (6)
C10—H10	0.9300	C39—C42	1.525 (5)
C11—C12	1.365 (6)	C40—C41	1.387 (6)
C12—C13	1.369 (6)	C40—H40	0.9300
C13—H13	0.9300	C41—H41	0.9300
C14—H14A	0.9600	C42—H42A	0.9600
C14—H14B	0.9600	C42—H42B	0.9600
C14—H14C	0.9600	C42—H42C	0.9600
O5—S1—O6	120.3 (2)	C17—C18—C19	118.8 (5)
O5—S1—O4	109.69 (19)	C17—C18—C21	122.4 (6)
O6—S1—O4	102.1 (2)	C19—C18—C21	118.7 (6)
O5—S1—C15	110.0 (3)	C18—C19—C20	121.8 (5)
O6—S1—C15	109.4 (2)	C18—C19—H19	119.1
O4—S1—C15	104.0 (2)	C20—C19—H19	119.1
O11—S2—O12	121.2 (2)	C15—C20—C19	117.5 (5)
O11—S2—O10	109.42 (18)	C15—C20—H20	121.3
O12—S2—O10	101.74 (19)	C19—C20—H20	121.3
O11—S2—C36	110.5 (2)	C18—C21—H21A	109.5
O12—S2—C36	108.8 (2)	C18—C21—H21B	109.5
O10—S2—C36	103.54 (19)	H21A—C21—H21B	109.5
C12—O3—C14	117.5 (4)	C18—C21—H21C	109.5
C11—O4—S1	120.4 (3)	H21A—C21—H21C	109.5
C33—O9—C35	118.3 (3)	H21B—C21—H21C	109.5
C32—O10—S2	121.2 (3)	C27—C22—C23	120.3 (5)
O1—N1—O2	120.9 (6)	C27—C22—N4	119.2 (5)
O1—N1—C1	120.4 (5)	C23—C22—N4	120.5 (5)
O2—N1—C1	118.7 (5)	C24—C23—C22	119.9 (4)
N3—N2—C4	119.6 (4)	C24—C23—H23	120.0
N3—N2—H2	120.2	C22—C23—H23	120.0
C4—N2—H2	120.2	C23—C24—C25	121.0 (4)
C7—N3—N2	116.6 (4)	C23—C24—H24	119.5
O8—N4—O7	122.5 (5)	C25—C24—H24	119.5
O8—N4—C22	119.0 (6)	N5—C25—C24	120.1 (4)
O7—N4—C22	118.4 (6)	N5—C25—C26	121.5 (4)
C25—N5—N6	121.0 (3)	C24—C25—C26	118.4 (4)
C25—N5—H5	119.5	C27—C26—C25	120.1 (4)
N6—N5—H5	119.5	C27—C26—H26	119.9
C28—N6—N5	116.7 (4)	C25—C26—H26	119.9
C6—C1—C2	120.2 (5)	C26—C27—C22	120.3 (5)
C6—C1—N1	120.2 (5)	C26—C27—H27	119.9
C2—C1—N1	119.5 (5)	C22—C27—H27	119.9
C3—C2—C1	120.5 (5)	N6—C28—C29	121.9 (4)
C3—C2—H2A	119.8	N6—C28—H28	119.0
C1—C2—H2A	119.8	C29—C28—H28	119.0
C2—C3—C4	119.8 (5)	C34—C29—C30	118.9 (4)
C2—C3—H3	120.1	C34—C29—C28	119.9 (4)
C4—C3—H3	120.1	C30—C29—C28	121.1 (4)
N2—C4—C3	122.2 (4)	C31—C30—C29	119.3 (5)
N2—C4—C5	118.9 (4)	C31—C30—H30	120.3
C3—C4—C5	118.9 (5)	C29—C30—H30	120.3
C6—C5—C4	119.4 (5)	C32—C31—C30	120.2 (5)
C6—C5—H5A	120.3	C32—C31—H31	119.9
C4—C5—H5A	120.3	C30—C31—H31	119.9
C5—C6—C1	121.2 (5)	C31—C32—C33	121.0 (4)
C5—C6—H6	119.4	C31—C32—O10	118.8 (4)
C1—C6—H6	119.4	C33—C32—O10	119.9 (4)
N3—C7—C8	119.8 (4)	O9—C33—C34	125.7 (4)
N3—C7—H7	120.1	O9—C33—C32	116.3 (4)
C8—C7—H7	120.1	C34—C33—C32	118.0 (5)
C9—C8—C13	117.3 (5)	C29—C34—C33	122.5 (4)
C9—C8—C7	124.0 (5)	C29—C34—H34	118.7
C13—C8—C7	118.7 (5)	C33—C34—H34	118.7
C10—C9—C8	122.5 (5)	O9—C35—H35A	109.5
C10—C9—H9	118.8	O9—C35—H35B	109.5
C8—C9—H9	118.8	H35A—C35—H35B	109.5
C9—C10—C11	118.9 (5)	O9—C35—H35C	109.5
C9—C10—H10	120.6	H35A—C35—H35C	109.5
C11—C10—H10	120.6	H35B—C35—H35C	109.5
C12—C11—C10	121.8 (5)	C37—C36—C41	120.4 (5)
C12—C11—O4	119.8 (4)	C37—C36—S2	120.5 (4)
C10—C11—O4	118.2 (5)	C41—C36—S2	118.8 (4)
C11—C12—O3	116.3 (5)	C36—C37—C38	120.4 (5)
C11—C12—C13	119.1 (5)	C36—C37—H37	119.8
O3—C12—C13	124.5 (5)	C38—C37—H37	119.8
C12—C13—C8	120.4 (5)	C39—C38—C37	120.3 (5)
C12—C13—H13	119.8	C39—C38—H38	119.8
C8—C13—H13	119.8	C37—C38—H38	119.8
O3—C14—H14A	109.5	C38—C39—C40	118.5 (5)
O3—C14—H14B	109.5	C38—C39—C42	120.0 (5)
H14A—C14—H14B	109.5	C40—C39—C42	121.5 (5)
O3—C14—H14C	109.5	C39—C40—C41	121.7 (5)
H14A—C14—H14C	109.5	C39—C40—H40	119.1
H14B—C14—H14C	109.5	C41—C40—H40	119.1
C20—C15—C16	121.9 (5)	C36—C41—C40	118.6 (5)
C20—C15—S1	119.7 (5)	C36—C41—H41	120.7
C16—C15—S1	118.4 (5)	C40—C41—H41	120.7
C15—C16—C17	119.3 (5)	C39—C42—H42A	109.5
C15—C16—H16	120.4	C39—C42—H42B	109.5
C17—C16—H16	120.4	H42A—C42—H42B	109.5
C18—C17—C16	120.6 (5)	C39—C42—H42C	109.5
C18—C17—H17	119.7	H42A—C42—H42C	109.5
C16—C17—H17	119.7	H42B—C42—H42C	109.5
O5—S1—O4—C11	35.7 (4)	C21—C18—C19—C20	179.3 (4)
O6—S1—O4—C11	164.3 (3)	C16—C15—C20—C19	1.7 (7)
C15—S1—O4—C11	−81.9 (4)	S1—C15—C20—C19	−176.9 (3)
O11—S2—O10—C32	32.5 (4)	C18—C19—C20—C15	−3.1 (7)
O12—S2—O10—C32	161.8 (3)	O8—N4—C22—C27	−1.3 (9)
C36—S2—O10—C32	−85.3 (4)	O7—N4—C22—C27	−178.4 (5)
C4—N2—N3—C7	176.9 (5)	O8—N4—C22—C23	−179.1 (5)
C25—N5—N6—C28	179.3 (5)	O7—N4—C22—C23	3.9 (9)
O1—N1—C1—C6	179.1 (6)	C27—C22—C23—C24	0.6 (8)
O2—N1—C1—C6	−2.1 (9)	N4—C22—C23—C24	178.3 (5)
O1—N1—C1—C2	1.1 (9)	C22—C23—C24—C25	0.4 (8)
O2—N1—C1—C2	179.9 (5)	N6—N5—C25—C24	−176.9 (4)
C6—C1—C2—C3	1.1 (8)	N6—N5—C25—C26	2.9 (7)
N1—C1—C2—C3	179.1 (5)	C23—C24—C25—N5	178.9 (5)
C1—C2—C3—C4	−1.8 (8)	C23—C24—C25—C26	−1.0 (8)
N3—N2—C4—C3	3.7 (7)	N5—C25—C26—C27	−179.4 (5)
N3—N2—C4—C5	−177.2 (4)	C24—C25—C26—C27	0.5 (8)
C2—C3—C4—N2	−178.8 (5)	C25—C26—C27—C22	0.5 (8)
C2—C3—C4—C5	2.1 (7)	C23—C22—C27—C26	−1.0 (8)
N2—C4—C5—C6	179.2 (5)	N4—C22—C27—C26	−178.8 (5)
C3—C4—C5—C6	−1.6 (8)	N5—N6—C28—C29	−178.0 (4)
C4—C5—C6—C1	1.0 (9)	N6—C28—C29—C34	175.6 (5)
C2—C1—C6—C5	−0.7 (9)	N6—C28—C29—C30	−3.4 (7)
N1—C1—C6—C5	−178.7 (5)	C34—C29—C30—C31	0.4 (8)
N2—N3—C7—C8	−179.2 (4)	C28—C29—C30—C31	179.4 (5)
N3—C7—C8—C9	−6.6 (8)	C29—C30—C31—C32	−0.2 (8)
N3—C7—C8—C13	172.2 (5)	C30—C31—C32—C33	−0.3 (8)
C13—C8—C9—C10	−1.0 (8)	C30—C31—C32—O10	−174.0 (4)
C7—C8—C9—C10	177.9 (5)	S2—O10—C32—C31	−92.5 (5)
C8—C9—C10—C11	1.5 (8)	S2—O10—C32—C33	93.7 (5)
C9—C10—C11—C12	−1.4 (7)	C35—O9—C33—C34	7.5 (8)
C9—C10—C11—O4	−175.5 (4)	C35—O9—C33—C32	−173.6 (5)
S1—O4—C11—C12	95.4 (5)	C31—C32—C33—O9	−178.4 (4)
S1—O4—C11—C10	−90.5 (5)	O10—C32—C33—O9	−4.8 (7)
C10—C11—C12—O3	−175.7 (5)	C31—C32—C33—C34	0.5 (7)
O4—C11—C12—O3	−1.8 (7)	O10—C32—C33—C34	174.2 (4)
C10—C11—C12—C13	0.9 (8)	C30—C29—C34—C33	−0.1 (8)
O4—C11—C12—C13	174.8 (4)	C28—C29—C34—C33	−179.1 (4)
C14—O3—C12—C11	−165.0 (4)	O9—C33—C34—C29	178.5 (5)
C14—O3—C12—C13	18.6 (7)	C32—C33—C34—C29	−0.4 (8)
C11—C12—C13—C8	−0.4 (8)	O11—S2—C36—C37	175.9 (3)
O3—C12—C13—C8	175.9 (5)	O12—S2—C36—C37	40.6 (4)
C9—C8—C13—C12	0.4 (7)	O10—S2—C36—C37	−67.0 (4)
C7—C8—C13—C12	−178.5 (5)	O11—S2—C36—C41	−9.5 (4)
O5—S1—C15—C20	−7.9 (4)	O12—S2—C36—C41	−144.8 (4)
O6—S1—C15—C20	−142.1 (4)	O10—S2—C36—C41	107.5 (4)
O4—S1—C15—C20	109.5 (4)	C41—C36—C37—C38	2.1 (7)
O5—S1—C15—C16	173.5 (4)	S2—C36—C37—C38	176.6 (3)
O6—S1—C15—C16	39.3 (4)	C36—C37—C38—C39	−1.6 (7)
O4—S1—C15—C16	−69.2 (4)	C37—C38—C39—C40	0.7 (7)
C20—C15—C16—C17	−1.4 (7)	C37—C38—C39—C42	−179.1 (4)
S1—C15—C16—C17	177.2 (4)	C38—C39—C40—C41	−0.3 (8)
C15—C16—C17—C18	2.5 (7)	C42—C39—C40—C41	179.5 (4)
C16—C17—C18—C19	−3.8 (8)	C37—C36—C41—C40	−1.7 (7)
C16—C17—C18—C21	−178.8 (4)	S2—C36—C41—C40	−176.3 (3)
C17—C18—C19—C20	4.2 (8)	C39—C40—C41—C36	0.8 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6^i	0.86	2.13	2.981 (5)	168
N5—H5···O12^ii	0.86	2.25	3.107 (5)	172
C14—H14B···O1^iii	0.96	2.58	3.476 (6)	156
C35—H35B···O8^iii	0.96	2.56	3.482 (6)	161

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+1/2, z; (iii) x, y−1, z.