Composite host lattices of 4,4′-sulfonyl­dibenzoate water/boric acid in two tetra­propyl­ammonium inclusion compounds

Two novel inclusion compounds of 4,4′-sulfonyl­dibenzoate anions and tetra­propyl­ammonium cations with different ancillary mol­ecules of water and boric acid, namely bis­(tetra­propyl­ammonium) 4,4′-sulfonyl­dibenzoate dihydrate, 2C₁₂H₂₈N⁺·C₁₄H₈O₆S²⁻·H₂O (1), and bis­(tetra­propyl­ammonium) 4,4′-sulfonyl­dibenzoate bis­(boric acid), 2C₁₂H₂₈N⁺·C₁₄H₈O₆S²⁻·2H₃BO₃ (2), were prepared and characterized using single-crystal X-ray diffraction. In the two salts, the host 4,4′-sulfonyldi­benzoic acid mol­ecules, which are converted to the corresponding anions under basic conditions, can be regarded as proton acceptors which link different proton donors of the ancillary mol­ecules of water or boric acid. In this way, an isolated hydrogen-bonded tetra­mer is constructed in salt 1 and a ribbon is constructed in salt 2. The tetra­mers and ribbons are then packed in a repeating manner to generate various host frameworks, and the tetra­propyl­ammonium guest counter-ions are contained in the cavities of the host lattices to give the final stable crystal structures. In these two salts, although the host anion and guest cation are the same, the difference in the ancillary small mol­ecules results in different structures, indicating the significance of ancillary mol­ecules in the formation of crystal structures.

Computing details

For both structures, data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008) for compound1; SHELXL2014 (Sheldrick, 2015) for compound2. For both structures, software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(tetrapropylammonium) 4,4'-sulfonyldibenzoate dihydrate (compound1)

Crystal data

2C12H28N^+·C14H8O6S^2^−·H2O	Z = 2
Mr = 694.98	F(000) = 760
Triclinic, P1	Dx = 1.128 Mg m^−3
a = 9.2201 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3675 (3) Å	Cell parameters from 6400 reflections
c = 24.2874 (9) Å	θ = 2.5–26.0°
α = 96.303 (2)°	µ = 0.13 mm^−1
β = 97.731 (2)°	T = 296 K
γ = 97.049 (2)°	Block, colorless
V = 2045.82 (13) Å^3	0.51 × 0.41 × 0.12 mm

Data collection

Bruker SMART CCD area detector diffractometer	5608 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.018
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
	k = −10→11
16331 measured reflections	l = −28→28
7187 independent reflections

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.094P)^2 + 0.2759P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
7187 reflections	Δρmax = 0.45 e Å^−3
439 parameters	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Crystals of 1 and 2 were mounted on glass fibers for intensity data collection at room temperature using a Bruker SMART Apex II diffractometer equipped with a CCD area detector (Bruker, 2004). The structures were solved via the direct method and refined via the full matrix least squares method based on F² using the structure determination and graphics package SHELXTL (Sheldrick, 2015). Normally, non-hydrogen atoms were refined with anisotropic displacement parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.45378 (6)	0.97098 (5)	0.27281 (2)	0.06107 (18)
O1	0.52027 (18)	1.05035 (16)	0.23310 (7)	0.0783 (5)
C1	0.5894 (2)	0.88012 (19)	0.30665 (8)	0.0516 (4)
N1	0.07898 (16)	0.24102 (16)	0.39035 (6)	0.0496 (4)
O1W	−0.1853 (3)	0.5324 (5)	−0.00432 (11)	0.1538 (12)
H1WB	−0.123 (5)	0.605 (5)	−0.011 (2)	0.231*
H1WA	−0.137 (5)	0.506 (5)	0.0252 (14)	0.231*
O2	0.38863 (18)	1.04808 (17)	0.31525 (8)	0.0836 (5)
C2	0.7047 (2)	0.8451 (2)	0.27906 (8)	0.0566 (5)
H2B	0.7070	0.8641	0.2424	0.068*
N2	0.50400 (18)	0.36863 (17)	0.12263 (7)	0.0548 (4)
O3	1.0366 (2)	0.6505 (2)	0.36376 (7)	0.0892 (6)
C3	0.8164 (2)	0.7816 (2)	0.30645 (8)	0.0567 (5)
H3A	0.8941	0.7586	0.2880	0.068*
O4	0.9380 (2)	0.6759 (2)	0.44218 (7)	0.0827 (5)
C4	0.8145 (2)	0.75178 (19)	0.36101 (8)	0.0505 (4)
O5	0.0011 (2)	0.4690 (2)	0.08911 (7)	0.0885 (5)
C5	0.6953 (2)	0.7840 (2)	0.38717 (8)	0.0575 (5)
H5A	0.6908	0.7615	0.4233	0.069*
O6	−0.0687 (2)	0.4097 (2)	0.16817 (8)	0.0974 (6)
C6	0.5839 (2)	0.8483 (2)	0.36077 (9)	0.0587 (5)
H6A	0.5056	0.8702	0.3791	0.070*
C7	0.9423 (2)	0.6875 (2)	0.39210 (9)	0.0596 (5)
C8	0.3182 (2)	0.8338 (2)	0.23481 (8)	0.0532 (5)
C9	0.2270 (2)	0.7484 (2)	0.26267 (9)	0.0579 (5)
H9A	0.2338	0.7650	0.3015	0.069*
C10	0.1254 (2)	0.6379 (2)	0.23178 (8)	0.0574 (5)
H10A	0.0645	0.5792	0.2502	0.069*
C11	0.1126 (2)	0.6131 (2)	0.17401 (8)	0.0540 (5)
C12	0.2012 (2)	0.7036 (2)	0.14664 (9)	0.0608 (5)
H12A	0.1906	0.6906	0.1077	0.073*
C13	0.3048 (2)	0.8126 (2)	0.17687 (9)	0.0609 (5)
H13A	0.3654	0.8717	0.1585	0.073*
C14	0.0051 (2)	0.4857 (3)	0.14105 (10)	0.0669 (6)
C15	0.2079 (2)	0.3600 (2)	0.39212 (9)	0.0584 (5)
H15A	0.2918	0.3149	0.3824	0.070*
H15B	0.1816	0.4204	0.3634	0.070*
C16	0.2564 (2)	0.4571 (3)	0.44686 (9)	0.0697 (6)
H16A	0.1745	0.5039	0.4577	0.084*
H16B	0.2890	0.4003	0.4761	0.084*
C17	0.3809 (3)	0.5693 (3)	0.43957 (11)	0.0768 (6)
H17A	0.4131	0.6321	0.4742	0.115*
H17B	0.4617	0.5222	0.4291	0.115*
H17C	0.3476	0.6254	0.4108	0.115*
C18	−0.0546 (2)	0.3127 (2)	0.40146 (9)	0.0597 (5)
H18A	−0.0391	0.3546	0.4405	0.072*
H18B	−0.0603	0.3918	0.3790	0.072*
C19	−0.2008 (2)	0.2159 (3)	0.38956 (11)	0.0748 (6)
H19A	−0.2252	0.1842	0.3496	0.090*
H19B	−0.1941	0.1307	0.4086	0.090*
C20	−0.3196 (3)	0.2949 (3)	0.40900 (13)	0.0917 (8)
H20A	−0.4122	0.2318	0.4011	0.138*
H20B	−0.2960	0.3251	0.4486	0.138*
H20C	−0.3270	0.3785	0.3898	0.138*
C21	0.1105 (2)	0.1419 (2)	0.43491 (9)	0.0613 (5)
H21A	0.1113	0.1965	0.4713	0.074*
H21B	0.0292	0.0631	0.4297	0.074*
C22	0.2514 (3)	0.0776 (3)	0.43610 (12)	0.0930 (9)
H22A	0.3345	0.1539	0.4476	0.112*
H22B	0.2586	0.0335	0.3987	0.112*
C23	0.2592 (3)	−0.0348 (3)	0.47563 (11)	0.0909 (8)
H23A	0.3507	−0.0737	0.4754	0.136*
H23B	0.2539	0.0090	0.5128	0.136*
H23C	0.1781	−0.1114	0.4640	0.136*
C24	0.0543 (2)	0.1517 (2)	0.33314 (8)	0.0601 (5)
H24A	0.1432	0.1088	0.3286	0.072*
H24B	−0.0246	0.0727	0.3328	0.072*
C25	0.0160 (3)	0.2282 (3)	0.28298 (10)	0.0842 (7)
H25A	−0.0733	0.2714	0.2862	0.101*
H25B	0.0953	0.3053	0.2814	0.101*
C26	−0.0069 (5)	0.1229 (4)	0.23032 (11)	0.1154 (11)
H26A	−0.0312	0.1727	0.1986	0.173*
H26B	0.0821	0.0812	0.2270	0.173*
H26C	−0.0862	0.0474	0.2318	0.173*
C27	0.5399 (3)	0.3710 (2)	0.18538 (8)	0.0656 (6)
H27A	0.5291	0.2717	0.1938	0.079*
H27B	0.6428	0.4118	0.1970	0.079*
C28	0.4471 (4)	0.4551 (3)	0.22000 (10)	0.0901 (8)
H28A	0.3437	0.4150	0.2094	0.108*
H28B	0.4585	0.5555	0.2129	0.108*
C29	0.4942 (5)	0.4477 (3)	0.28160 (11)	0.1167 (12)
H29A	0.4346	0.5015	0.3033	0.175*
H29B	0.4817	0.3483	0.2886	0.175*
H29C	0.5962	0.4885	0.2920	0.175*
C30	0.3445 (2)	0.3058 (2)	0.10101 (9)	0.0651 (5)
H30A	0.2818	0.3690	0.1175	0.078*
H30B	0.3276	0.3083	0.0609	0.078*
C31	0.2953 (3)	0.1543 (3)	0.11179 (12)	0.0816 (7)
H31A	0.3028	0.1507	0.1518	0.098*
H31B	0.3587	0.0892	0.0968	0.098*
C32	0.1357 (3)	0.1061 (3)	0.08408 (14)	0.1005 (9)
H32A	0.1045	0.0090	0.0911	0.151*
H32B	0.0732	0.1701	0.0993	0.151*
H32C	0.1289	0.1088	0.0444	0.151*
C33	0.6098 (2)	0.2777 (2)	0.09702 (10)	0.0703 (6)
H33A	0.7098	0.3245	0.1109	0.084*
H33B	0.5990	0.1842	0.1108	0.084*
C34	0.5936 (3)	0.2515 (4)	0.03504 (12)	0.1007 (9)
H34A	0.6088	0.3430	0.0200	0.121*
H34B	0.4950	0.2033	0.0198	0.121*
C35	0.7095 (4)	0.1556 (4)	0.01870 (18)	0.1450 (16)
H35A	0.7005	0.1376	−0.0214	0.217*
H35B	0.8068	0.2043	0.0338	0.217*
H35C	0.6933	0.0651	0.0336	0.217*
C36	0.5244 (3)	0.5211 (2)	0.10648 (9)	0.0658 (6)
H36A	0.5073	0.5139	0.0659	0.079*
H36B	0.4486	0.5723	0.1203	0.079*
C37	0.6711 (3)	0.6114 (3)	0.12706 (12)	0.0844 (7)
H37A	0.7486	0.5617	0.1139	0.101*
H37B	0.6883	0.6236	0.1677	0.101*
C38	0.6778 (4)	0.7589 (3)	0.10686 (14)	0.1037 (9)
H38A	0.7730	0.8142	0.1207	0.156*
H38B	0.6625	0.7471	0.0666	0.156*
H38C	0.6023	0.8090	0.1204	0.156*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0589 (3)	0.0458 (3)	0.0786 (4)	0.0119 (2)	0.0104 (3)	0.0033 (2)
O1	0.0746 (10)	0.0573 (9)	0.1058 (13)	0.0055 (7)	0.0109 (9)	0.0306 (9)
C1	0.0515 (10)	0.0403 (9)	0.0615 (12)	0.0028 (8)	0.0121 (9)	−0.0006 (8)
N1	0.0478 (8)	0.0517 (9)	0.0514 (9)	0.0071 (7)	0.0137 (7)	0.0084 (7)
O1W	0.1074 (18)	0.279 (4)	0.1015 (17)	0.083 (2)	0.0185 (14)	0.073 (2)
O2	0.0746 (10)	0.0694 (10)	0.1035 (13)	0.0262 (8)	0.0113 (9)	−0.0199 (9)
C2	0.0618 (12)	0.0592 (12)	0.0500 (11)	0.0099 (9)	0.0135 (9)	0.0051 (9)
N2	0.0596 (10)	0.0535 (9)	0.0514 (9)	0.0166 (7)	0.0022 (7)	0.0045 (7)
O3	0.0819 (11)	0.1205 (15)	0.0841 (12)	0.0478 (11)	0.0290 (9)	0.0388 (11)
C3	0.0577 (11)	0.0603 (12)	0.0560 (11)	0.0140 (9)	0.0183 (9)	0.0057 (9)
O4	0.0995 (13)	0.0961 (12)	0.0566 (9)	0.0313 (10)	0.0086 (8)	0.0121 (8)
C4	0.0554 (11)	0.0401 (9)	0.0538 (11)	0.0006 (8)	0.0108 (8)	0.0000 (8)
O5	0.0851 (12)	0.1089 (14)	0.0622 (10)	0.0064 (10)	−0.0053 (8)	−0.0024 (9)
C5	0.0667 (13)	0.0537 (11)	0.0519 (11)	0.0030 (9)	0.0168 (9)	0.0028 (9)
O6	0.0905 (13)	0.0999 (14)	0.0882 (12)	−0.0241 (11)	−0.0105 (10)	0.0231 (11)
C6	0.0590 (12)	0.0569 (12)	0.0620 (12)	0.0082 (9)	0.0222 (10)	−0.0003 (9)
C7	0.0658 (13)	0.0519 (11)	0.0615 (13)	0.0081 (9)	0.0105 (10)	0.0084 (9)
C8	0.0493 (10)	0.0515 (11)	0.0623 (12)	0.0145 (8)	0.0128 (9)	0.0077 (9)
C9	0.0575 (11)	0.0661 (12)	0.0522 (11)	0.0133 (10)	0.0134 (9)	0.0055 (9)
C10	0.0492 (11)	0.0663 (12)	0.0598 (12)	0.0091 (9)	0.0137 (9)	0.0133 (10)
C11	0.0459 (10)	0.0619 (12)	0.0561 (11)	0.0148 (9)	0.0059 (8)	0.0106 (9)
C12	0.0641 (12)	0.0684 (13)	0.0527 (11)	0.0159 (10)	0.0095 (9)	0.0116 (10)
C13	0.0637 (12)	0.0609 (12)	0.0645 (13)	0.0134 (10)	0.0201 (10)	0.0178 (10)
C14	0.0540 (12)	0.0769 (15)	0.0668 (14)	0.0124 (11)	−0.0052 (10)	0.0104 (12)
C15	0.0489 (11)	0.0628 (12)	0.0650 (12)	0.0040 (9)	0.0137 (9)	0.0127 (10)
C16	0.0580 (12)	0.0782 (15)	0.0677 (14)	−0.0049 (11)	0.0074 (10)	0.0053 (11)
C17	0.0608 (13)	0.0763 (15)	0.0882 (17)	−0.0046 (11)	0.0115 (12)	0.0035 (13)
C18	0.0502 (11)	0.0600 (12)	0.0687 (13)	0.0087 (9)	0.0137 (9)	−0.0001 (10)
C19	0.0557 (13)	0.0783 (15)	0.0883 (16)	0.0003 (11)	0.0168 (11)	0.0038 (13)
C20	0.0525 (13)	0.113 (2)	0.107 (2)	0.0106 (13)	0.0190 (13)	−0.0056 (17)
C21	0.0686 (13)	0.0628 (12)	0.0549 (12)	0.0073 (10)	0.0148 (10)	0.0136 (10)
C22	0.0914 (19)	0.114 (2)	0.0916 (18)	0.0454 (17)	0.0236 (15)	0.0457 (17)
C23	0.114 (2)	0.0709 (16)	0.0853 (18)	0.0218 (15)	−0.0067 (15)	0.0161 (13)
C24	0.0638 (12)	0.0642 (12)	0.0533 (11)	0.0099 (10)	0.0155 (9)	0.0028 (9)
C25	0.1009 (19)	0.0917 (18)	0.0600 (14)	0.0132 (15)	0.0072 (13)	0.0158 (13)
C26	0.173 (3)	0.114 (2)	0.0547 (15)	0.006 (2)	0.0140 (18)	0.0097 (15)
C27	0.0902 (16)	0.0532 (12)	0.0513 (11)	0.0164 (11)	−0.0038 (10)	0.0084 (9)
C28	0.144 (3)	0.0716 (16)	0.0630 (14)	0.0301 (16)	0.0304 (15)	0.0113 (12)
C29	0.207 (4)	0.0780 (18)	0.0595 (15)	−0.003 (2)	0.0259 (19)	0.0023 (13)
C30	0.0573 (12)	0.0736 (14)	0.0647 (13)	0.0181 (10)	0.0016 (10)	0.0094 (11)
C31	0.0750 (16)	0.0779 (16)	0.0901 (18)	0.0085 (12)	0.0046 (13)	0.0145 (13)
C32	0.0733 (17)	0.100 (2)	0.120 (2)	0.0036 (15)	0.0042 (16)	0.0014 (18)
C33	0.0573 (12)	0.0670 (13)	0.0814 (15)	0.0155 (10)	0.0036 (11)	−0.0125 (11)
C34	0.0891 (19)	0.122 (2)	0.0849 (19)	0.0159 (17)	0.0196 (15)	−0.0220 (17)
C35	0.127 (3)	0.142 (3)	0.157 (3)	0.020 (2)	0.054 (3)	−0.063 (3)
C36	0.0792 (15)	0.0636 (13)	0.0599 (12)	0.0215 (11)	0.0123 (11)	0.0163 (10)
C37	0.0933 (18)	0.0692 (15)	0.0905 (18)	0.0105 (13)	0.0150 (14)	0.0093 (13)
C38	0.126 (3)	0.0809 (18)	0.107 (2)	−0.0012 (17)	0.0305 (19)	0.0231 (16)

Geometric parameters (Å, º)

S1—O2	1.4334 (16)	C20—H20B	0.9600
S1—O1	1.4365 (17)	C20—H20C	0.9600
S1—C8	1.761 (2)	C21—C22	1.496 (3)
S1—C1	1.761 (2)	C21—H21A	0.9700
C1—C2	1.385 (3)	C21—H21B	0.9700
C1—C6	1.386 (3)	C22—C23	1.502 (3)
N1—C18	1.514 (2)	C22—H22A	0.9700
N1—C24	1.515 (2)	C22—H22B	0.9700
N1—C15	1.519 (2)	C23—H23A	0.9600
N1—C21	1.523 (2)	C23—H23B	0.9600
O1W—H1WB	0.879 (10)	C23—H23C	0.9600
O1W—H1WA	0.870 (10)	C24—C25	1.503 (3)
C2—C3	1.381 (3)	C24—H24A	0.9700
C2—H2B	0.9300	C24—H24B	0.9700
N2—C27	1.513 (2)	C25—C26	1.501 (4)
N2—C30	1.515 (3)	C25—H25A	0.9700
N2—C36	1.519 (3)	C25—H25B	0.9700
N2—C33	1.522 (3)	C26—H26A	0.9600
O3—C7	1.238 (3)	C26—H26B	0.9600
C3—C4	1.386 (3)	C26—H26C	0.9600
C3—H3A	0.9300	C27—C28	1.508 (3)
O4—C7	1.238 (3)	C27—H27A	0.9700
C4—C5	1.389 (3)	C27—H27B	0.9700
C4—C7	1.535 (3)	C28—C29	1.513 (4)
O5—C14	1.249 (3)	C28—H28A	0.9700
C5—C6	1.374 (3)	C28—H28B	0.9700
C5—H5A	0.9300	C29—H29A	0.9600
O6—C14	1.228 (3)	C29—H29B	0.9600
C6—H6A	0.9300	C29—H29C	0.9600
C8—C9	1.382 (3)	C30—C31	1.498 (3)
C8—C13	1.386 (3)	C30—H30A	0.9700
C9—C10	1.383 (3)	C30—H30B	0.9700
C9—H9A	0.9300	C31—C32	1.525 (4)
C10—C11	1.383 (3)	C31—H31A	0.9700
C10—H10A	0.9300	C31—H31B	0.9700
C11—C12	1.388 (3)	C32—H32A	0.9600
C11—C14	1.528 (3)	C32—H32B	0.9600
C12—C13	1.379 (3)	C32—H32C	0.9600
C12—H12A	0.9300	C33—C34	1.483 (4)
C13—H13A	0.9300	C33—H33A	0.9700
C15—C16	1.506 (3)	C33—H33B	0.9700
C15—H15A	0.9700	C34—C35	1.542 (4)
C15—H15B	0.9700	C34—H34A	0.9700
C16—C17	1.501 (3)	C34—H34B	0.9700
C16—H16A	0.9700	C35—H35A	0.9600
C16—H16B	0.9700	C35—H35B	0.9600
C17—H17A	0.9600	C35—H35C	0.9600
C17—H17B	0.9600	C36—C37	1.497 (3)
C17—H17C	0.9600	C36—H36A	0.9700
C18—C19	1.503 (3)	C36—H36B	0.9700
C18—H18A	0.9700	C37—C38	1.513 (4)
C18—H18B	0.9700	C37—H37A	0.9700
C19—C20	1.494 (3)	C37—H37B	0.9700
C19—H19A	0.9700	C38—H38A	0.9600
C19—H19B	0.9700	C38—H38B	0.9600
C20—H20A	0.9600	C38—H38C	0.9600
O2—S1—O1	118.91 (10)	C21—C22—C23	111.6 (2)
O2—S1—C8	108.36 (10)	C21—C22—H22A	109.3
O1—S1—C8	107.68 (10)	C23—C22—H22A	109.3
O2—S1—C1	107.72 (10)	C21—C22—H22B	109.3
O1—S1—C1	107.76 (9)	C23—C22—H22B	109.3
C8—S1—C1	105.67 (9)	H22A—C22—H22B	108.0
C2—C1—C6	120.25 (18)	C22—C23—H23A	109.5
C2—C1—S1	119.00 (15)	C22—C23—H23B	109.5
C6—C1—S1	120.71 (15)	H23A—C23—H23B	109.5
C18—N1—C24	111.97 (15)	C22—C23—H23C	109.5
C18—N1—C15	107.86 (14)	H23A—C23—H23C	109.5
C24—N1—C15	108.05 (14)	H23B—C23—H23C	109.5
C18—N1—C21	108.62 (14)	C25—C24—N1	117.48 (18)
C24—N1—C21	108.79 (15)	C25—C24—H24A	107.9
C15—N1—C21	111.58 (15)	N1—C24—H24A	107.9
H1WB—O1W—H1WA	102 (2)	C25—C24—H24B	107.9
C3—C2—C1	119.47 (18)	N1—C24—H24B	107.9
C3—C2—H2B	120.3	H24A—C24—H24B	107.2
C1—C2—H2B	120.3	C26—C25—C24	110.1 (2)
C27—N2—C30	111.71 (17)	C26—C25—H25A	109.6
C27—N2—C36	110.95 (16)	C24—C25—H25A	109.6
C30—N2—C36	106.32 (15)	C26—C25—H25B	109.6
C27—N2—C33	106.14 (15)	C24—C25—H25B	109.6
C30—N2—C33	111.20 (16)	H25A—C25—H25B	108.2
C36—N2—C33	110.60 (16)	C25—C26—H26A	109.5
C2—C3—C4	121.09 (18)	C25—C26—H26B	109.5
C2—C3—H3A	119.5	H26A—C26—H26B	109.5
C4—C3—H3A	119.5	C25—C26—H26C	109.5
C3—C4—C5	118.30 (18)	H26A—C26—H26C	109.5
C3—C4—C7	120.83 (17)	H26B—C26—H26C	109.5
C5—C4—C7	120.86 (18)	C28—C27—N2	115.72 (18)
C6—C5—C4	121.39 (19)	C28—C27—H27A	108.3
C6—C5—H5A	119.3	N2—C27—H27A	108.3
C4—C5—H5A	119.3	C28—C27—H27B	108.3
C5—C6—C1	119.43 (18)	N2—C27—H27B	108.3
C5—C6—H6A	120.3	H27A—C27—H27B	107.4
C1—C6—H6A	120.3	C27—C28—C29	110.1 (3)
O4—C7—O3	127.4 (2)	C27—C28—H28A	109.7
O4—C7—C4	116.61 (19)	C29—C28—H28A	109.7
O3—C7—C4	115.97 (19)	C27—C28—H28B	109.7
C9—C8—C13	120.74 (19)	C29—C28—H28B	109.7
C9—C8—S1	120.16 (16)	H28A—C28—H28B	108.2
C13—C8—S1	119.10 (16)	C28—C29—H29A	109.5
C8—C9—C10	118.76 (19)	C28—C29—H29B	109.5
C8—C9—H9A	120.6	H29A—C29—H29B	109.5
C10—C9—H9A	120.6	C28—C29—H29C	109.5
C9—C10—C11	121.34 (19)	H29A—C29—H29C	109.5
C9—C10—H10A	119.3	H29B—C29—H29C	109.5
C11—C10—H10A	119.3	C31—C30—N2	117.00 (18)
C10—C11—C12	119.01 (19)	C31—C30—H30A	108.0
C10—C11—C14	120.37 (19)	N2—C30—H30A	108.0
C12—C11—C14	120.61 (19)	C31—C30—H30B	108.0
C13—C12—C11	120.34 (19)	N2—C30—H30B	108.0
C13—C12—H12A	119.8	H30A—C30—H30B	107.3
C11—C12—H12A	119.8	C30—C31—C32	109.7 (2)
C12—C13—C8	119.74 (19)	C30—C31—H31A	109.7
C12—C13—H13A	120.1	C32—C31—H31A	109.7
C8—C13—H13A	120.1	C30—C31—H31B	109.7
O6—C14—O5	126.4 (2)	C32—C31—H31B	109.7
O6—C14—C11	116.9 (2)	H31A—C31—H31B	108.2
O5—C14—C11	116.7 (2)	C31—C32—H32A	109.5
C16—C15—N1	116.66 (16)	C31—C32—H32B	109.5
C16—C15—H15A	108.1	H32A—C32—H32B	109.5
N1—C15—H15A	108.1	C31—C32—H32C	109.5
C16—C15—H15B	108.1	H32A—C32—H32C	109.5
N1—C15—H15B	108.1	H32B—C32—H32C	109.5
H15A—C15—H15B	107.3	C34—C33—N2	117.5 (2)
C17—C16—C15	108.52 (18)	C34—C33—H33A	107.9
C17—C16—H16A	110.0	N2—C33—H33A	107.9
C15—C16—H16A	110.0	C34—C33—H33B	107.9
C17—C16—H16B	110.0	N2—C33—H33B	107.9
C15—C16—H16B	110.0	H33A—C33—H33B	107.2
H16A—C16—H16B	108.4	C33—C34—C35	108.4 (3)
C16—C17—H17A	109.5	C33—C34—H34A	110.0
C16—C17—H17B	109.5	C35—C34—H34A	110.0
H17A—C17—H17B	109.5	C33—C34—H34B	110.0
C16—C17—H17C	109.5	C35—C34—H34B	110.0
H17A—C17—H17C	109.5	H34A—C34—H34B	108.4
H17B—C17—H17C	109.5	C34—C35—H35A	109.5
C19—C18—N1	115.99 (17)	C34—C35—H35B	109.5
C19—C18—H18A	108.3	H35A—C35—H35B	109.5
N1—C18—H18A	108.3	C34—C35—H35C	109.5
C19—C18—H18B	108.3	H35A—C35—H35C	109.5
N1—C18—H18B	108.3	H35B—C35—H35C	109.5
H18A—C18—H18B	107.4	C37—C36—N2	116.86 (18)
C20—C19—C18	110.4 (2)	C37—C36—H36A	108.1
C20—C19—H19A	109.6	N2—C36—H36A	108.1
C18—C19—H19A	109.6	C37—C36—H36B	108.1
C20—C19—H19B	109.6	N2—C36—H36B	108.1
C18—C19—H19B	109.6	H36A—C36—H36B	107.3
H19A—C19—H19B	108.1	C36—C37—C38	111.4 (2)
C19—C20—H20A	109.5	C36—C37—H37A	109.3
C19—C20—H20B	109.5	C38—C37—H37A	109.3
H20A—C20—H20B	109.5	C36—C37—H37B	109.3
C19—C20—H20C	109.5	C38—C37—H37B	109.3
H20A—C20—H20C	109.5	H37A—C37—H37B	108.0
H20B—C20—H20C	109.5	C37—C38—H38A	109.5
C22—C21—N1	116.64 (18)	C37—C38—H38B	109.5
C22—C21—H21A	108.1	H38A—C38—H38B	109.5
N1—C21—H21A	108.1	C37—C38—H38C	109.5
C22—C21—H21B	108.1	H38A—C38—H38C	109.5
N1—C21—H21B	108.1	H38B—C38—H38C	109.5
H21A—C21—H21B	107.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O5^i	0.88 (5)	2.41 (5)	2.840 (3)	110 (4)
O1W—H1WA···O5	0.87 (4)	1.96 (4)	2.820 (3)	170 (4)
C13—H13A···O1	0.93	2.48	2.879 (3)	106
C18—H18B···O3^ii	0.97	2.56	3.428 (3)	149
C21—H21A···O4^iii	0.97	2.43	3.384 (3)	169
C22—H22B···O2^iv	0.97	2.50	3.347 (3)	146
C24—H24A···O2^iv	0.97	2.45	3.411 (3)	169
C26—H26A···O6	0.96	2.46	3.295 (4)	145
C27—H27A···O1^iv	0.97	2.37	3.330 (2)	169
C30—H30B···O1W^i	0.97	2.51	3.220 (4)	130
C33—H33A···O6^v	0.97	2.31	3.249 (3)	163

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

Bis(tetrapropylammonium) 4,4'-sulfonyldibenzoate bis(boric acid) (compound2)

Crystal data

2C12H28N^+·C14H8O6S^2^−·2BH3O3	F(000) = 1736
Mr = 800.64	Dx = 1.179 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.184 (2) Å	Cell parameters from 2841 reflections
b = 11.2494 (9) Å	θ = 2.4–22.1°
c = 15.9615 (11) Å	µ = 0.13 mm^−1
β = 93.796 (2)°	T = 296 K
V = 4512.1 (6) Å^3	Block, colorless
Z = 4	0.35 × 0.13 × 0.06 mm

Data collection

Bruker SMART CCD area detector diffractometer	4279 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.036
phi and ω scans	θmax = 23.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −27→28
Tmin = 0.940, Tmax = 0.985	k = −12→10
16098 measured reflections	l = −17→18
6866 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.8703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6866 reflections	Δρmax = 0.32 e Å^−3
557 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.21031 (11)	0.6018 (2)	0.81576 (16)	0.0479 (7)
N1	0.10877 (8)	0.42464 (18)	0.15613 (13)	0.0482 (6)
O1	0.29520 (8)	0.72032 (17)	0.86894 (13)	0.0693 (6)
B1	0.02133 (15)	0.6218 (3)	0.5943 (2)	0.0585 (9)
S1	0.26392 (3)	0.69447 (6)	0.79269 (5)	0.0552 (2)
C2	0.21917 (11)	0.5129 (2)	0.87489 (17)	0.0542 (7)
H2A	0.2520	0.5062	0.9048	0.065*
B2	0.43318 (16)	0.4107 (3)	0.9520 (2)	0.0643 (10)
N2	0.38693 (9)	0.0227 (2)	0.78313 (14)	0.0556 (6)
O2	0.24286 (8)	0.79152 (16)	0.74212 (13)	0.0670 (6)
C3	0.17888 (11)	0.4347 (2)	0.88886 (16)	0.0522 (7)
H3A	0.1848	0.3741	0.9280	0.063*
O3	0.09966 (8)	0.26691 (19)	0.90369 (15)	0.0794 (7)
C4	0.12945 (11)	0.4442 (2)	0.84572 (16)	0.0464 (7)
O4	0.04149 (9)	0.3716 (2)	0.82470 (15)	0.0865 (7)
C5	0.12111 (11)	0.5347 (2)	0.78721 (17)	0.0531 (7)
H5A	0.0880	0.5429	0.7584	0.064*
O5	0.41814 (10)	0.2908 (2)	0.61597 (14)	0.0874 (7)
C6	0.16145 (11)	0.6123 (2)	0.77158 (17)	0.0543 (7)
H6A	0.1559	0.6717	0.7314	0.065*
O6	0.35925 (11)	0.3281 (2)	0.51064 (15)	0.0947 (8)
C7	0.08633 (12)	0.3550 (3)	0.85932 (18)	0.0538 (7)
O7	−0.02881 (8)	0.60843 (17)	0.55752 (12)	0.0637 (5)
H7	−0.0586	0.6669	0.5749	0.096*
C8	0.30152 (11)	0.6017 (2)	0.73004 (18)	0.0500 (7)
O8	0.06067 (8)	0.54723 (19)	0.57369 (13)	0.0762 (6)
H8	0.0430	0.4851	0.5377	0.114*
C9	0.28522 (12)	0.5864 (3)	0.64632 (19)	0.0623 (8)
H9A	0.2570	0.6303	0.6220	0.075*
O9	0.03433 (8)	0.70864 (19)	0.65087 (13)	0.0760 (6)
H9	0.0078	0.7732	0.6653	0.114*
C10	0.31139 (12)	0.5051 (3)	0.59940 (18)	0.0627 (8)
H10A	0.3003	0.4941	0.5432	0.075*
O10	0.45984 (8)	0.3823 (2)	1.02564 (13)	0.0715 (6)
H10	0.4451 (13)	0.326 (2)	1.053 (2)	0.107*
C11	0.35375 (11)	0.4396 (2)	0.63390 (18)	0.0531 (7)
O11	0.38805 (10)	0.3563 (2)	0.92328 (14)	0.0917 (8)
H11	0.3789	0.2779	0.9572	0.138*
C12	0.37037 (12)	0.4594 (3)	0.71680 (19)	0.0617 (8)
H12A	0.3997	0.4182	0.7404	0.074*
O12	0.45166 (10)	0.5002 (2)	0.90457 (15)	0.0928 (8)
H12	0.4815 (9)	0.528 (4)	0.926 (3)	0.139*
C13	0.34420 (11)	0.5393 (3)	0.76535 (18)	0.0582 (8)
H13A	0.3554	0.5508	0.8215	0.070*
C14	0.37941 (13)	0.3459 (3)	0.5829 (2)	0.0633 (8)
C15	0.05235 (11)	0.3839 (3)	0.16651 (18)	0.0590 (8)
H15A	0.0535	0.3185	0.2062	0.071*
H15B	0.0332	0.4486	0.1911	0.071*
C16	0.02092 (13)	0.3442 (3)	0.0876 (2)	0.0796 (10)
H16A	0.0082	0.4133	0.0559	0.096*
H16B	0.0437	0.2988	0.0529	0.096*
C17	−0.02536 (14)	0.2695 (4)	0.1093 (3)	0.1108 (15)
H17A	−0.0450	0.2449	0.0586	0.166*
H17B	−0.0127	0.2007	0.1400	0.166*
H17C	−0.0481	0.3149	0.1431	0.166*
C18	0.13566 (11)	0.4474 (2)	0.24250 (16)	0.0546 (7)
H18A	0.1355	0.3738	0.2741	0.065*
H18B	0.1726	0.4678	0.2357	0.065*
C19	0.11187 (14)	0.5434 (3)	0.29416 (19)	0.0712 (9)
H19A	0.0757	0.5225	0.3056	0.085*
H19B	0.1110	0.6180	0.2637	0.085*
C20	0.14564 (15)	0.5560 (3)	0.3758 (2)	0.0923 (12)
H20A	0.1309	0.6170	0.4095	0.139*
H20B	0.1461	0.4820	0.4057	0.139*
H20C	0.1813	0.5772	0.3640	0.139*
C21	0.14064 (11)	0.3307 (2)	0.11281 (17)	0.0542 (7)
H21A	0.1280	0.3283	0.0541	0.065*
H21B	0.1775	0.3562	0.1152	0.065*
C22	0.13897 (13)	0.2064 (2)	0.1471 (2)	0.0667 (8)
H22A	0.1027	0.1766	0.1421	0.080*
H22B	0.1511	0.2062	0.2060	0.080*
C23	0.17433 (15)	0.1277 (3)	0.0984 (2)	0.0931 (12)
H23A	0.1734	0.0481	0.1200	0.140*
H23B	0.1619	0.1276	0.0402	0.140*
H23C	0.2102	0.1571	0.1040	0.140*
C24	0.10771 (12)	0.5364 (2)	0.10249 (17)	0.0580 (8)
H24A	0.0916	0.5169	0.0473	0.070*
H24B	0.0850	0.5944	0.1273	0.070*
C25	0.16127 (13)	0.5934 (3)	0.09187 (19)	0.0672 (9)
H25A	0.1847	0.5360	0.0680	0.081*
H25B	0.1771	0.6170	0.1464	0.081*
C26	0.15572 (15)	0.7015 (3)	0.0350 (2)	0.0846 (11)
H26A	0.1901	0.7360	0.0293	0.127*
H26B	0.1406	0.6779	−0.0192	0.127*
H26C	0.1330	0.7588	0.0591	0.127*
C27	0.3506 (3)	0.1305 (7)	0.7855 (4)	0.0708 (17)	0.659 (6)
H27A	0.3661	0.1850	0.8275	0.085*	0.659 (6)
H27D	0.3509	0.1703	0.7316	0.085*	0.659 (6)
C28	0.2940 (3)	0.1110 (8)	0.8038 (6)	0.092 (2)	0.659 (6)
H28A	0.2767	0.0630	0.7595	0.111*	0.659 (6)
H28B	0.2927	0.0675	0.8561	0.111*	0.659 (6)
C29	0.26533 (17)	0.2220 (4)	0.8102 (3)	0.1380 (19)	0.659 (6)
H29A	0.2291	0.2058	0.8220	0.207*	0.659 (6)
H29B	0.2820	0.2692	0.8547	0.207*	0.659 (6)
H29C	0.2659	0.2647	0.7582	0.207*	0.659 (6)
C30	0.3639 (2)	−0.0671 (6)	0.7181 (4)	0.0673 (17)	0.659 (6)
H30A	0.3864	−0.1372	0.7202	0.081*	0.659 (6)
H30B	0.3289	−0.0912	0.7338	0.081*	0.659 (6)
C31	0.3590 (4)	−0.0225 (9)	0.6301 (5)	0.115 (3)	0.659 (6)
H31A	0.3396	0.0520	0.6293	0.138*	0.659 (6)
H31B	0.3944	−0.0056	0.6128	0.138*	0.659 (6)
C32	0.3328 (2)	−0.1014 (5)	0.5686 (3)	0.1393 (18)	0.659 (6)
H32A	0.3317	−0.0647	0.5142	0.209*	0.659 (6)
H32B	0.3522	−0.1748	0.5672	0.209*	0.659 (6)
H32C	0.2972	−0.1171	0.5837	0.209*	0.659 (6)
C33	0.4408 (2)	0.0639 (6)	0.7620 (4)	0.0709 (17)	0.659 (6)
H33A	0.4591	−0.0063	0.7437	0.085*	0.659 (6)
H33B	0.4350	0.1141	0.7129	0.085*	0.659 (6)
C34	0.4762 (2)	0.1222 (6)	0.8144 (4)	0.189 (3)	0.659 (6)
H34A	0.4915	0.0616	0.8518	0.227*	0.659 (6)
H34B	0.4547	0.1719	0.8485	0.227*	0.659 (6)
C35	0.51916 (15)	0.1941 (4)	0.7948 (3)	0.1138 (14)	0.659 (6)
H35A	0.5370	0.2232	0.8457	0.171*	0.659 (6)
H35B	0.5436	0.1482	0.7643	0.171*	0.659 (6)
H35C	0.5063	0.2600	0.7610	0.171*	0.659 (6)
C36	0.3885 (2)	−0.0366 (5)	0.8693 (4)	0.0656 (17)	0.659 (6)
H36A	0.3927	0.0272	0.9101	0.079*	0.659 (6)
H36B	0.3533	−0.0694	0.8747	0.079*	0.659 (6)
C37	0.4227 (2)	−0.1213 (6)	0.8961 (4)	0.182 (3)	0.659 (6)
H37A	0.4574	−0.0891	0.8858	0.219*	0.659 (6)
H37B	0.4167	−0.1853	0.8558	0.219*	0.659 (6)
C38	0.4303 (2)	−0.1772 (5)	0.9711 (3)	0.150 (2)	0.659 (6)
H38A	0.4586	−0.2340	0.9686	0.225*	0.659 (6)
H38B	0.4395	−0.1197	1.0141	0.225*	0.659 (6)
H38C	0.3981	−0.2173	0.9837	0.225*	0.659 (6)
C27'	0.3352 (5)	0.0644 (12)	0.8127 (7)	0.064 (3)	0.341 (6)
H27B	0.3406	0.0870	0.8713	0.077*	0.341 (6)
H27C	0.3103	−0.0017	0.8095	0.077*	0.341 (6)
C28'	0.3100 (8)	0.1683 (13)	0.7642 (10)	0.093 (4)	0.341 (6)
H28C	0.3368	0.2284	0.7562	0.111*	0.341 (6)
H28D	0.2962	0.1414	0.7092	0.111*	0.341 (6)
C29'	0.26533 (17)	0.2220 (4)	0.8102 (3)	0.1380 (19)	0.341 (6)
H29D	0.2501	0.2874	0.7783	0.207*	0.341 (6)
H29E	0.2385	0.1630	0.8173	0.207*	0.341 (6)
H29F	0.2790	0.2499	0.8642	0.207*	0.341 (6)
C30'	0.3843 (4)	0.0027 (11)	0.6885 (8)	0.065 (3)	0.341 (6)
H30C	0.3772	0.0785	0.6611	0.078*	0.341 (6)
H30D	0.4191	−0.0235	0.6734	0.078*	0.341 (6)
C31'	0.3439 (6)	−0.0850 (15)	0.6538 (10)	0.088 (4)	0.341 (6)
H31C	0.3543	−0.1619	0.6770	0.106*	0.341 (6)
H31D	0.3105	−0.0644	0.6772	0.106*	0.341 (6)
C32'	0.3328 (2)	−0.1014 (5)	0.5686 (3)	0.1393 (18)	0.341 (6)
H32D	0.3058	−0.1613	0.5598	0.209*	0.341 (6)
H32E	0.3204	−0.0281	0.5436	0.209*	0.341 (6)
H32F	0.3645	−0.1264	0.5433	0.209*	0.341 (6)
C33'	0.4296 (5)	0.1236 (10)	0.8021 (7)	0.065 (3)	0.341 (6)
H33C	0.4235	0.1787	0.7557	0.077*	0.341 (6)
H33D	0.4173	0.1642	0.8508	0.077*	0.341 (6)
C34'	0.4762 (2)	0.1222 (6)	0.8144 (4)	0.189 (3)	0.341 (6)
H34C	0.4858	0.0450	0.7930	0.227*	0.341 (6)
H34D	0.4809	0.1151	0.8750	0.227*	0.341 (6)
C35'	0.51916 (15)	0.1941 (4)	0.7948 (3)	0.1138 (14)	0.341 (6)
H35D	0.5518	0.1592	0.8177	0.171*	0.341 (6)
H35E	0.5201	0.2004	0.7349	0.171*	0.341 (6)
H35F	0.5151	0.2718	0.8184	0.171*	0.341 (6)
C36'	0.4061 (5)	−0.0911 (10)	0.8267 (8)	0.075 (4)	0.341 (6)
H36C	0.3766	−0.1451	0.8147	0.090*	0.341 (6)
H36D	0.4337	−0.1183	0.7917	0.090*	0.341 (6)
C37'	0.4227 (2)	−0.1213 (6)	0.8961 (4)	0.182 (3)	0.341 (6)
H37C	0.4221	−0.0420	0.9198	0.219*	0.341 (6)
H37D	0.4593	−0.1301	0.8815	0.219*	0.341 (6)
C38'	0.4303 (2)	−0.1772 (5)	0.9711 (3)	0.150 (2)	0.341 (6)
H38D	0.4600	−0.1421	1.0027	0.225*	0.341 (6)
H38E	0.3989	−0.1691	1.0016	0.225*	0.341 (6)
H38F	0.4373	−0.2599	0.9621	0.225*	0.341 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0543 (17)	0.0436 (16)	0.0466 (16)	0.0008 (13)	0.0091 (14)	0.0000 (13)
N1	0.0517 (13)	0.0474 (13)	0.0451 (13)	0.0016 (11)	−0.0002 (11)	0.0010 (11)
O1	0.0699 (14)	0.0690 (14)	0.0678 (14)	−0.0123 (11)	−0.0036 (11)	−0.0119 (11)
B1	0.060 (2)	0.057 (2)	0.059 (2)	0.0101 (18)	0.0070 (18)	0.0099 (18)
S1	0.0562 (4)	0.0459 (4)	0.0641 (5)	−0.0052 (3)	0.0083 (4)	0.0028 (4)
C2	0.0512 (17)	0.0605 (18)	0.0508 (17)	−0.0024 (15)	0.0020 (14)	0.0084 (15)
B2	0.072 (3)	0.069 (2)	0.051 (2)	−0.004 (2)	0.000 (2)	−0.0050 (19)
N2	0.0584 (15)	0.0530 (15)	0.0556 (16)	−0.0068 (12)	0.0053 (12)	−0.0010 (12)
O2	0.0682 (13)	0.0451 (11)	0.0887 (15)	0.0030 (10)	0.0126 (11)	0.0168 (11)
C3	0.0579 (18)	0.0534 (17)	0.0457 (17)	−0.0002 (14)	0.0063 (14)	0.0083 (13)
O3	0.0665 (14)	0.0689 (14)	0.1019 (17)	−0.0153 (11)	−0.0013 (12)	0.0294 (14)
C4	0.0527 (17)	0.0440 (16)	0.0440 (16)	0.0012 (13)	0.0133 (13)	−0.0040 (13)
O4	0.0609 (15)	0.0845 (16)	0.1124 (19)	−0.0174 (12)	−0.0082 (14)	0.0334 (14)
C5	0.0502 (17)	0.0530 (17)	0.0558 (18)	0.0005 (14)	0.0017 (14)	0.0024 (15)
O5	0.0910 (17)	0.0992 (18)	0.0710 (15)	0.0376 (15)	−0.0022 (13)	−0.0089 (13)
C6	0.0576 (19)	0.0488 (17)	0.0564 (18)	0.0009 (14)	0.0024 (15)	0.0078 (14)
O6	0.123 (2)	0.0982 (18)	0.0607 (15)	0.0389 (16)	−0.0075 (14)	−0.0099 (13)
C7	0.0563 (19)	0.0523 (18)	0.0535 (18)	−0.0046 (15)	0.0090 (15)	0.0007 (15)
O7	0.0542 (12)	0.0597 (13)	0.0774 (14)	0.0105 (10)	0.0063 (11)	−0.0098 (10)
C8	0.0503 (17)	0.0483 (16)	0.0515 (18)	−0.0055 (13)	0.0043 (14)	0.0062 (14)
O8	0.0613 (13)	0.0789 (15)	0.0873 (16)	0.0232 (11)	−0.0039 (11)	−0.0114 (12)
C9	0.0584 (19)	0.065 (2)	0.063 (2)	0.0097 (15)	0.0012 (16)	0.0120 (16)
O9	0.0669 (14)	0.0798 (15)	0.0801 (15)	0.0142 (11)	−0.0035 (11)	−0.0198 (13)
C10	0.071 (2)	0.070 (2)	0.0467 (18)	0.0070 (17)	0.0005 (16)	0.0063 (16)
O10	0.0657 (14)	0.0846 (16)	0.0634 (15)	−0.0130 (12)	−0.0027 (11)	0.0148 (12)
C11	0.0549 (18)	0.0543 (17)	0.0507 (18)	−0.0013 (14)	0.0086 (14)	0.0084 (14)
O11	0.1046 (19)	0.0938 (17)	0.0725 (15)	−0.0321 (15)	−0.0263 (14)	0.0139 (13)
C12	0.0576 (19)	0.064 (2)	0.063 (2)	0.0103 (15)	0.0010 (16)	0.0052 (16)
O12	0.105 (2)	0.1017 (19)	0.0683 (16)	−0.0320 (16)	−0.0191 (14)	0.0263 (14)
C13	0.0602 (19)	0.0630 (19)	0.0505 (18)	0.0009 (16)	−0.0025 (15)	0.0017 (15)
C14	0.073 (2)	0.063 (2)	0.054 (2)	0.0086 (17)	0.0081 (17)	0.0067 (17)
C15	0.0481 (17)	0.0631 (19)	0.066 (2)	−0.0032 (14)	0.0042 (15)	−0.0037 (15)
C16	0.065 (2)	0.089 (2)	0.083 (2)	−0.0084 (18)	−0.0095 (18)	−0.008 (2)
C17	0.062 (2)	0.152 (4)	0.120 (3)	−0.031 (2)	0.017 (2)	−0.058 (3)
C18	0.0607 (18)	0.0595 (18)	0.0432 (17)	−0.0054 (14)	0.0010 (14)	0.0029 (14)
C19	0.090 (2)	0.068 (2)	0.057 (2)	−0.0065 (18)	0.0108 (18)	−0.0120 (16)
C20	0.115 (3)	0.101 (3)	0.062 (2)	−0.022 (2)	0.009 (2)	−0.024 (2)
C21	0.0574 (17)	0.0557 (18)	0.0495 (17)	0.0022 (14)	0.0036 (14)	0.0001 (14)
C22	0.079 (2)	0.0507 (18)	0.071 (2)	0.0022 (16)	0.0083 (17)	0.0003 (16)
C23	0.107 (3)	0.062 (2)	0.112 (3)	0.018 (2)	0.024 (2)	−0.006 (2)
C24	0.068 (2)	0.0538 (18)	0.0506 (17)	0.0034 (15)	−0.0039 (15)	0.0049 (14)
C25	0.080 (2)	0.0587 (19)	0.062 (2)	−0.0093 (17)	−0.0058 (17)	0.0100 (16)
C26	0.109 (3)	0.062 (2)	0.082 (2)	−0.0096 (19)	0.004 (2)	0.0173 (18)
C27	0.066 (4)	0.062 (4)	0.083 (4)	0.001 (4)	−0.011 (3)	−0.003 (3)
C28	0.065 (5)	0.090 (6)	0.121 (6)	0.012 (4)	−0.006 (4)	−0.015 (4)
C29	0.080 (3)	0.120 (4)	0.209 (5)	0.025 (3)	−0.024 (3)	−0.060 (4)
C30	0.071 (4)	0.062 (4)	0.069 (5)	−0.012 (3)	0.011 (3)	−0.002 (3)
C31	0.149 (8)	0.132 (7)	0.063 (6)	−0.067 (6)	−0.003 (5)	0.011 (5)
C32	0.152 (4)	0.173 (5)	0.091 (3)	−0.028 (4)	−0.005 (3)	−0.038 (3)
C33	0.066 (4)	0.084 (4)	0.063 (4)	−0.016 (3)	0.000 (3)	0.008 (3)
C34	0.117 (4)	0.214 (6)	0.224 (7)	−0.110 (5)	−0.082 (4)	0.102 (5)
C35	0.082 (3)	0.128 (4)	0.132 (4)	−0.034 (3)	0.007 (3)	0.017 (3)
C36	0.060 (3)	0.064 (3)	0.073 (4)	0.002 (3)	0.004 (3)	0.006 (3)
C37	0.137 (5)	0.225 (7)	0.176 (6)	−0.049 (5)	−0.058 (4)	0.132 (5)
C38	0.168 (5)	0.153 (4)	0.126 (4)	0.029 (4)	−0.008 (4)	0.058 (4)
C27'	0.062 (8)	0.066 (8)	0.067 (7)	−0.006 (7)	0.017 (6)	−0.011 (6)
C28'	0.088 (11)	0.082 (10)	0.108 (11)	0.021 (9)	0.013 (9)	0.008 (8)
C29'	0.080 (3)	0.120 (4)	0.209 (5)	0.025 (3)	−0.024 (3)	−0.060 (4)
C30'	0.077 (7)	0.068 (7)	0.053 (7)	−0.015 (6)	0.011 (6)	−0.006 (6)
C31'	0.112 (11)	0.111 (11)	0.040 (9)	−0.035 (9)	0.000 (7)	−0.015 (8)
C32'	0.152 (4)	0.173 (5)	0.091 (3)	−0.028 (4)	−0.005 (3)	−0.038 (3)
C33'	0.093 (8)	0.055 (6)	0.050 (6)	0.001 (6)	0.032 (6)	−0.004 (5)
C34'	0.117 (4)	0.214 (6)	0.224 (7)	−0.110 (5)	−0.082 (4)	0.102 (5)
C35'	0.082 (3)	0.128 (4)	0.132 (4)	−0.034 (3)	0.007 (3)	0.017 (3)
C36'	0.082 (8)	0.060 (7)	0.087 (8)	−0.005 (6)	0.036 (7)	−0.019 (7)
C37'	0.137 (5)	0.225 (7)	0.176 (6)	−0.049 (5)	−0.058 (4)	0.132 (5)
C38'	0.168 (5)	0.153 (4)	0.126 (4)	0.029 (4)	−0.008 (4)	0.058 (4)

Geometric parameters (Å, º)

C1—C6	1.382 (4)	C24—C25	1.513 (4)
C1—C2	1.383 (4)	C24—H24A	0.9700
C1—S1	1.764 (3)	C24—H24B	0.9700
N1—C15	1.513 (3)	C25—C26	1.518 (4)
N1—C18	1.517 (3)	C25—H25A	0.9700
N1—C21	1.520 (3)	C25—H25B	0.9700
N1—C24	1.520 (3)	C26—H26A	0.9600
O1—S1	1.435 (2)	C26—H26B	0.9600
B1—O8	1.355 (4)	C26—H26C	0.9600
B1—O9	1.356 (4)	C27—C28	1.491 (11)
B1—O7	1.365 (4)	C27—H27A	0.9700
S1—O2	1.4380 (19)	C27—H27D	0.9700
S1—C8	1.764 (3)	C28—C29	1.449 (9)
C2—C3	1.372 (4)	C28—H28A	0.9700
C2—H2A	0.9300	C28—H28B	0.9700
B2—O11	1.344 (4)	C29—H29A	0.9600
B2—O10	1.353 (4)	C29—H29B	0.9600
B2—O12	1.360 (4)	C29—H29C	0.9600
N2—C27'	1.491 (12)	C30—C31	1.490 (11)
N2—C33	1.492 (6)	C30—H30A	0.9700
N2—C36'	1.521 (12)	C30—H30B	0.9700
N2—C27	1.521 (7)	C31—C32	1.449 (10)
N2—C30'	1.524 (12)	C31—H31A	0.9700
N2—C36	1.527 (6)	C31—H31B	0.9700
N2—C30	1.534 (7)	C32—H32A	0.9600
N2—C33'	1.579 (12)	C32—H32B	0.9600
C3—C4	1.386 (4)	C32—H32C	0.9600
C3—H3A	0.9300	C33—C34	1.351 (7)
O3—C7	1.251 (3)	C33—H33A	0.9700
C4—C5	1.388 (4)	C33—H33B	0.9700
C4—C7	1.505 (4)	C34—C35	1.403 (6)
O4—C7	1.238 (3)	C34—H34A	0.9700
C5—C6	1.375 (4)	C34—H34B	0.9700
C5—H5A	0.9300	C35—H35A	0.9600
O5—C14	1.244 (4)	C35—H35B	0.9600
C6—H6A	0.9300	C35—H35C	0.9600
O6—C14	1.245 (3)	C36—C37	1.335 (7)
O7—H7	1.0489	C36—H36A	0.9700
C8—C13	1.373 (4)	C36—H36B	0.9700
C8—C9	1.383 (4)	C37—C38	1.355 (6)
O8—H8	0.9912	C37—H37A	0.9700
C9—C10	1.377 (4)	C37—H37B	0.9700
C9—H9A	0.9300	C38—H38A	0.9600
O9—H9	1.0229	C38—H38B	0.9600
C10—C11	1.381 (4)	C38—H38C	0.9600
C10—H10A	0.9300	C27'—C28'	1.52 (2)
O10—H10	0.861 (10)	C27'—H27B	0.9700
C11—C12	1.379 (4)	C27'—H27C	0.9700
C11—C14	1.504 (4)	C28'—C29'	1.509 (17)
O11—H11	1.0684	C28'—H28C	0.9700
C12—C13	1.383 (4)	C28'—H28D	0.9700
C12—H12A	0.9300	C29'—H29D	0.9600
O12—H12	0.861 (10)	C29'—H29E	0.9600
C13—H13A	0.9300	C29'—H29F	0.9600
C15—C16	1.510 (4)	C30'—C31'	1.50 (2)
C15—H15A	0.9700	C30'—H30C	0.9700
C15—H15B	0.9700	C30'—H30D	0.9700
C16—C17	1.496 (5)	C31'—C32'	1.383 (15)
C16—H16A	0.9700	C31'—H31C	0.9700
C16—H16B	0.9700	C31'—H31D	0.9700
C17—H17A	0.9600	C32'—H32D	0.9600
C17—H17B	0.9600	C32'—H32E	0.9600
C17—H17C	0.9600	C32'—H32F	0.9600
C18—C19	1.506 (4)	C33'—C34'	1.176 (11)
C18—H18A	0.9700	C33'—H33C	0.9700
C18—H18B	0.9700	C33'—H33D	0.9700
C19—C20	1.515 (4)	C34'—C35'	1.403 (6)
C19—H19A	0.9700	C34'—H34C	0.9700
C19—H19B	0.9700	C34'—H34D	0.9700
C20—H20A	0.9600	C35'—H35D	0.9600
C20—H20B	0.9600	C35'—H35E	0.9600
C20—H20C	0.9600	C35'—H35F	0.9600
C21—C22	1.504 (4)	C36'—C37'	1.206 (11)
C21—H21A	0.9700	C36'—H36C	0.9700
C21—H21B	0.9700	C36'—H36D	0.9700
C22—C23	1.507 (4)	C37'—C38'	1.355 (6)
C22—H22A	0.9700	C37'—H37C	0.9700
C22—H22B	0.9700	C37'—H37D	0.9700
C23—H23A	0.9600	C38'—H38D	0.9600
C23—H23B	0.9600	C38'—H38E	0.9600
C23—H23C	0.9600	C38'—H38F	0.9600
C6—C1—C2	120.6 (3)	C25—C26—H26C	109.5
C6—C1—S1	120.7 (2)	H26A—C26—H26C	109.5
C2—C1—S1	118.6 (2)	H26B—C26—H26C	109.5
C15—N1—C18	108.5 (2)	C28—C27—N2	118.2 (8)
C15—N1—C21	111.6 (2)	C28—C27—H27A	107.8
C18—N1—C21	108.27 (19)	N2—C27—H27A	107.8
C15—N1—C24	109.3 (2)	C28—C27—H27D	107.8
C18—N1—C24	111.2 (2)	N2—C27—H27D	107.8
C21—N1—C24	107.97 (19)	H27A—C27—H27D	107.1
O8—B1—O9	117.4 (3)	C29—C28—C27	111.9 (8)
O8—B1—O7	119.8 (3)	C29—C28—H28A	109.2
O9—B1—O7	122.8 (3)	C27—C28—H28A	109.2
O1—S1—O2	118.92 (12)	C29—C28—H28B	109.2
O1—S1—C8	108.38 (13)	C27—C28—H28B	109.2
O2—S1—C8	108.83 (13)	H28A—C28—H28B	107.9
O1—S1—C1	109.12 (12)	C28—C29—H29A	109.5
O2—S1—C1	107.90 (13)	C28—C29—H29B	109.5
C8—S1—C1	102.45 (12)	H29A—C29—H29B	109.5
C3—C2—C1	119.1 (3)	C28—C29—H29C	109.5
C3—C2—H2A	120.4	H29A—C29—H29C	109.5
C1—C2—H2A	120.4	H29B—C29—H29C	109.5
O11—B2—O10	123.3 (3)	C31—C30—N2	114.8 (7)
O11—B2—O12	117.4 (3)	C31—C30—H30A	108.6
O10—B2—O12	119.3 (3)	N2—C30—H30A	108.6
C27'—N2—C36'	112.2 (7)	C31—C30—H30B	108.6
C33—N2—C27	108.4 (4)	N2—C30—H30B	108.6
C27'—N2—C30'	112.3 (6)	H30A—C30—H30B	107.5
C36'—N2—C30'	108.7 (6)	C32—C31—C30	116.0 (9)
C33—N2—C36	111.6 (3)	C32—C31—H31A	108.3
C27—N2—C36	107.8 (4)	C30—C31—H31A	108.3
C33—N2—C30	111.1 (4)	C32—C31—H31B	108.3
C27—N2—C30	109.9 (3)	C30—C31—H31B	108.3
C36—N2—C30	107.9 (3)	H31A—C31—H31B	107.4
C27'—N2—C33'	108.2 (6)	C31—C32—H32A	109.5
C36'—N2—C33'	109.0 (6)	C31—C32—H32B	109.5
C30'—N2—C33'	106.3 (6)	H32A—C32—H32B	109.5
C2—C3—C4	121.3 (3)	C31—C32—H32C	109.5
C2—C3—H3A	119.4	H32A—C32—H32C	109.5
C4—C3—H3A	119.4	H32B—C32—H32C	109.5
C3—C4—C5	118.8 (2)	C34—C33—N2	125.7 (7)
C3—C4—C7	120.6 (3)	C34—C33—H33A	105.9
C5—C4—C7	120.5 (3)	N2—C33—H33A	105.9
C6—C5—C4	120.5 (3)	C34—C33—H33B	105.9
C6—C5—H5A	119.8	N2—C33—H33B	105.9
C4—C5—H5A	119.8	H33A—C33—H33B	106.2
C5—C6—C1	119.8 (3)	C33—C34—C35	129.0 (6)
C5—C6—H6A	120.1	C33—C34—H34A	105.0
C1—C6—H6A	120.1	C35—C34—H34A	105.0
O4—C7—O3	125.1 (3)	C33—C34—H34B	105.0
O4—C7—C4	118.7 (3)	C35—C34—H34B	105.0
O3—C7—C4	116.2 (3)	H34A—C34—H34B	105.9
B1—O7—H7	118.3	C34—C35—H35A	109.5
C13—C8—C9	120.5 (3)	C34—C35—H35B	109.5
C13—C8—S1	120.3 (2)	H35A—C35—H35B	109.5
C9—C8—S1	119.1 (2)	C34—C35—H35C	109.5
B1—O8—H8	105.6	H35A—C35—H35C	109.5
C10—C9—C8	119.1 (3)	H35B—C35—H35C	109.5
C10—C9—H9A	120.4	C37—C36—N2	125.3 (6)
C8—C9—H9A	120.4	C37—C36—H36A	106.0
B1—O9—H9	121.9	N2—C36—H36A	106.0
C9—C10—C11	121.5 (3)	C37—C36—H36B	106.0
C9—C10—H10A	119.3	N2—C36—H36B	106.0
C11—C10—H10A	119.3	H36A—C36—H36B	106.3
B2—O10—H10	114 (3)	C36—C37—C38	131.5 (8)
C12—C11—C10	118.3 (3)	C36—C37—H37A	104.4
C12—C11—C14	121.2 (3)	C38—C37—H37A	104.4
C10—C11—C14	120.4 (3)	C36—C37—H37B	104.4
B2—O11—H11	114.1	C38—C37—H37B	104.4
C11—C12—C13	121.1 (3)	H37A—C37—H37B	105.6
C11—C12—H12A	119.4	C37—C38—H38A	109.5
C13—C12—H12A	119.4	C37—C38—H38B	109.5
B2—O12—H12	112 (3)	H38A—C38—H38B	109.5
C8—C13—C12	119.5 (3)	C37—C38—H38C	109.5
C8—C13—H13A	120.3	H38A—C38—H38C	109.5
C12—C13—H13A	120.3	H38B—C38—H38C	109.5
O5—C14—O6	125.0 (3)	N2—C27'—C28'	115.2 (14)
O5—C14—C11	118.2 (3)	N2—C27'—H27B	108.5
O6—C14—C11	116.8 (3)	C28'—C27'—H27B	108.5
C16—C15—N1	116.3 (2)	N2—C27'—H27C	108.5
C16—C15—H15A	108.2	C28'—C27'—H27C	108.5
N1—C15—H15A	108.2	H27B—C27'—H27C	107.5
C16—C15—H15B	108.2	C29'—C28'—C27'	111.1 (13)
N1—C15—H15B	108.2	C29'—C28'—H28C	109.4
H15A—C15—H15B	107.4	C27'—C28'—H28C	109.4
C17—C16—C15	110.3 (3)	C29'—C28'—H28D	109.4
C17—C16—H16A	109.6	C27'—C28'—H28D	109.4
C15—C16—H16A	109.6	H28C—C28'—H28D	108.0
C17—C16—H16B	109.6	C28'—C29'—H29D	109.5
C15—C16—H16B	109.6	C28'—C29'—H29E	109.5
H16A—C16—H16B	108.1	H29D—C29'—H29E	109.5
C16—C17—H17A	109.5	C28'—C29'—H29F	109.5
C16—C17—H17B	109.5	H29D—C29'—H29F	109.5
H17A—C17—H17B	109.5	H29E—C29'—H29F	109.5
C16—C17—H17C	109.5	C31'—C30'—N2	116.5 (12)
H17A—C17—H17C	109.5	C31'—C30'—H30C	108.2
H17B—C17—H17C	109.5	N2—C30'—H30C	108.2
C19—C18—N1	116.7 (2)	C31'—C30'—H30D	108.2
C19—C18—H18A	108.1	N2—C30'—H30D	108.2
N1—C18—H18A	108.1	H30C—C30'—H30D	107.3
C19—C18—H18B	108.1	C32'—C31'—C30'	122.7 (16)
N1—C18—H18B	108.1	C32'—C31'—H31C	106.7
H18A—C18—H18B	107.3	C30'—C31'—H31C	106.7
C18—C19—C20	108.5 (3)	C32'—C31'—H31D	106.7
C18—C19—H19A	110.0	C30'—C31'—H31D	106.7
C20—C19—H19A	110.0	H31C—C31'—H31D	106.6
C18—C19—H19B	110.0	C31'—C32'—H32D	109.5
C20—C19—H19B	110.0	C31'—C32'—H32E	109.5
H19A—C19—H19B	108.4	H32D—C32'—H32E	109.5
C19—C20—H20A	109.5	C31'—C32'—H32F	109.5
C19—C20—H20B	109.5	H32D—C32'—H32F	109.5
H20A—C20—H20B	109.5	H32E—C32'—H32F	109.5
C19—C20—H20C	109.5	C34'—C33'—N2	133.0 (10)
H20A—C20—H20C	109.5	C34'—C33'—H33C	104.0
H20B—C20—H20C	109.5	N2—C33'—H33C	104.0
C22—C21—N1	116.9 (2)	C34'—C33'—H33D	104.0
C22—C21—H21A	108.1	N2—C33'—H33D	104.0
N1—C21—H21A	108.1	H33C—C33'—H33D	105.5
C22—C21—H21B	108.1	C33'—C34'—C35'	137.0 (7)
N1—C21—H21B	108.1	C33'—C34'—H34C	102.9
H21A—C21—H21B	107.3	C35'—C34'—H34C	102.9
C21—C22—C23	109.1 (3)	C33'—C34'—H34D	102.9
C21—C22—H22A	109.9	C35'—C34'—H34D	102.9
C23—C22—H22A	109.9	H34C—C34'—H34D	105.1
C21—C22—H22B	109.9	C34'—C35'—H35D	109.5
C23—C22—H22B	109.9	C34'—C35'—H35E	109.5
H22A—C22—H22B	108.3	H35D—C35'—H35E	109.5
C22—C23—H23A	109.5	C34'—C35'—H35F	109.5
C22—C23—H23B	109.5	H35D—C35'—H35F	109.5
H23A—C23—H23B	109.5	H35E—C35'—H35F	109.5
C22—C23—H23C	109.5	C37'—C36'—N2	137.5 (11)
H23A—C23—H23C	109.5	C37'—C36'—H36C	102.7
H23B—C23—H23C	109.5	N2—C36'—H36C	102.7
C25—C24—N1	115.5 (2)	C37'—C36'—H36D	102.7
C25—C24—H24A	108.4	N2—C36'—H36D	102.7
N1—C24—H24A	108.4	H36C—C36'—H36D	105.0
C25—C24—H24B	108.4	C36'—C37'—C38'	164.1 (8)
N1—C24—H24B	108.4	C36'—C37'—H37C	94.9
H24A—C24—H24B	107.5	C38'—C37'—H37C	94.9
C24—C25—C26	111.0 (3)	C36'—C37'—H37D	94.9
C24—C25—H25A	109.4	C38'—C37'—H37D	94.9
C26—C25—H25A	109.4	H37C—C37'—H37D	103.2
C24—C25—H25B	109.4	C37'—C38'—H38D	109.5
C26—C25—H25B	109.4	C37'—C38'—H38E	109.5
H25A—C25—H25B	108.0	H38D—C38'—H38E	109.5
C25—C26—H26A	109.5	C37'—C38'—H38F	109.5
C25—C26—H26B	109.5	H38D—C38'—H38F	109.5
H26A—C26—H26B	109.5	H38E—C38'—H38F	109.5
C6—C1—S1—O1	145.3 (2)	C15—N1—C18—C19	−62.1 (3)
C2—C1—S1—O1	−39.1 (2)	C21—N1—C18—C19	176.6 (2)
C6—C1—S1—O2	14.8 (3)	C24—N1—C18—C19	58.2 (3)
C2—C1—S1—O2	−169.6 (2)	N1—C18—C19—C20	−177.5 (2)
C6—C1—S1—C8	−99.9 (2)	C15—N1—C21—C22	−49.6 (3)
C2—C1—S1—C8	75.7 (2)	C18—N1—C21—C22	69.7 (3)
C6—C1—C2—C3	0.4 (4)	C24—N1—C21—C22	−169.7 (2)
S1—C1—C2—C3	−175.2 (2)	N1—C21—C22—C23	−177.9 (3)
C1—C2—C3—C4	−0.9 (4)	C15—N1—C24—C25	175.6 (2)
C2—C3—C4—C5	0.2 (4)	C18—N1—C24—C25	55.7 (3)
C2—C3—C4—C7	177.7 (2)	C21—N1—C24—C25	−62.9 (3)
C3—C4—C5—C6	0.9 (4)	N1—C24—C25—C26	178.1 (2)
C7—C4—C5—C6	−176.5 (2)	C33—N2—C27—C28	178.8 (6)
C4—C5—C6—C1	−1.4 (4)	C36—N2—C27—C28	−60.2 (7)
C2—C1—C6—C5	0.8 (4)	C30—N2—C27—C28	57.1 (7)
S1—C1—C6—C5	176.3 (2)	N2—C27—C28—C29	175.7 (5)
C3—C4—C7—O4	174.4 (3)	C33—N2—C30—C31	−57.9 (6)
C5—C4—C7—O4	−8.2 (4)	C27—N2—C30—C31	62.0 (7)
C3—C4—C7—O3	−7.6 (4)	C36—N2—C30—C31	179.4 (6)
C5—C4—C7—O3	169.8 (3)	N2—C30—C31—C32	−174.5 (6)
O1—S1—C8—C13	19.0 (3)	C27—N2—C33—C34	73.9 (7)
O2—S1—C8—C13	149.7 (2)	C36—N2—C33—C34	−44.7 (8)
C1—S1—C8—C13	−96.3 (2)	C30—N2—C33—C34	−165.2 (6)
O1—S1—C8—C9	−165.5 (2)	N2—C33—C34—C35	−158.7 (6)
O2—S1—C8—C9	−34.8 (3)	C33—N2—C36—C37	−49.2 (7)
C1—S1—C8—C9	79.2 (2)	C27—N2—C36—C37	−168.1 (6)
C13—C8—C9—C10	1.8 (4)	C30—N2—C36—C37	73.2 (6)
S1—C8—C9—C10	−173.7 (2)	N2—C36—C37—C38	176.5 (6)
C8—C9—C10—C11	−0.6 (4)	C36'—N2—C27'—C28'	−172.4 (11)
C9—C10—C11—C12	−1.6 (4)	C30'—N2—C27'—C28'	−49.7 (14)
C9—C10—C11—C14	176.1 (3)	C33'—N2—C27'—C28'	67.3 (12)
C10—C11—C12—C13	2.4 (4)	N2—C27'—C28'—C29'	−166.7 (8)
C14—C11—C12—C13	−175.2 (3)	C27'—N2—C30'—C31'	−58.4 (13)
C9—C8—C13—C12	−1.0 (4)	C36'—N2—C30'—C31'	66.3 (12)
S1—C8—C13—C12	174.5 (2)	C33'—N2—C30'—C31'	−176.5 (10)
C11—C12—C13—C8	−1.2 (4)	N2—C30'—C31'—C32'	172.1 (10)
C12—C11—C14—O5	−3.9 (4)	C27'—N2—C33'—C34'	153.4 (12)
C10—C11—C14—O5	178.5 (3)	C36'—N2—C33'—C34'	31.1 (14)
C12—C11—C14—O6	174.7 (3)	C30'—N2—C33'—C34'	−85.8 (13)
C10—C11—C14—O6	−2.8 (4)	N2—C33'—C34'—C35'	143.1 (9)
C18—N1—C15—C16	−173.7 (2)	C27'—N2—C36'—C37'	−69.1 (15)
C21—N1—C15—C16	−54.5 (3)	C30'—N2—C36'—C37'	166.1 (13)
C24—N1—C15—C16	64.8 (3)	C33'—N2—C36'—C37'	50.7 (15)
N1—C15—C16—C17	160.7 (3)	N2—C36'—C37'—C38'	125 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O3^i	1.05	1.58	2.625 (3)	173
O8—H8···O7^ii	0.99	1.86	2.806 (3)	158
O9—H9···O4^i	1.02	1.68	2.694 (3)	171
O10—H10···O5^iii	0.87 (3)	1.81 (3)	2.678 (3)	176 (2)
O11—H11···O6^iii	1.07	1.57	2.628 (3)	173
O12—H12···O10^iv	0.86 (3)	1.91 (3)	2.762 (3)	169 (4)
C6—H6A···O2	0.93	2.57	2.936 (3)	104
C13—H13A···O1	0.93	2.58	2.945 (4)	104
C21—H21A···O3^v	0.97	2.55	3.502 (4)	166
C24—H24B···O9^vi	0.97	2.60	3.525 (3)	160
C25—H25B···O2^vi	0.97	2.41	3.316 (4)	156
C27—H27A···O11	0.97	2.50	3.450 (8)	166
C30—H30B···O2^vii	0.97	2.55	3.482 (6)	161
C33—H33B···O5	0.97	2.54	3.478 (7)	164
C36—H36A···O6^iii	0.97	2.47	3.370 (6)	154

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