Cinchonidinium bis­(4-methyl­benzene­sulfonate) monohydrate

In the title salt, C₁₉H₂₄N₂O²⁺·2C₇H₇SO₃⁻·H₂O, the ions and the water mol­ecule are held together by O—H...O, N—H...O and C—H...O hydrogen bonds, forming hydrogen-bonded layers; there are no hydrogen bonds between layers.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.113
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H0A    ..  H2N     ..       2.07 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.82(4), Rep   0.823(10) ......       4.00 su-Rat
              O8   -H0A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(4), Rep   0.829(10) ......       4.00 su-Rat
              O8   -H0B     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      108(4), Rep   108.0(17) ......       2.35 su-Rat
              H0A  -O8   -H0B     1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(4), Rep   0.823(10) ......       4.00 su-Rat
              O8   -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(4), Rep   0.829(10) ......       4.00 su-Rat
              O8   -H2#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(4), Rep   1.908(10) ......       4.00 su-Rat
              H1#  -O4      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.99(4), Rep   1.983(10) ......       4.00 su-Rat
              H2#  -O5      1.555   1.554

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.949
            Tmax scaled      0.943 Tmin scaled      0.884
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           26.00
           From the CIF: _reflns_number_total               6202
           Count of symmetry unique reflns         3101
           Completeness (_total/calc)            200.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3101
           Fraction of Friedel pairs measured     1.000
           Are heavy atom types Z>Si present        yes

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

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

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Cinchonidinium bis(4-methylbenzenesulfonate) monohydrate

Crystal data

C19H24N2O^2+·2C7H7SO3^−·H2O	Z = 1
Mr = 656.81	F(000) = 348
Triclinic, P1	Dx = 1.380 Mg m^−3
Hall symbol: P1	Mo Kα radiation, λ = 0.71073 Å
a = 6.565 (3) Å	Cell parameters from 43 reflections
b = 9.599 (4) Å	θ = 4.0–15.3°
c = 12.748 (5) Å	µ = 0.22 mm^−1
α = 85.25 (3)°	T = 291 K
β = 84.08 (3)°	Block, colorless
γ = 82.71 (3)°	0.54 × 0.42 × 0.26 mm
V = 790.6 (6) Å^3

Data collection

Siemens P4 diffractometer	5316 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.6°
ω scans	h = −8→8
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	k = −11→11
Tmin = 0.932, Tmax = 0.994	l = −15→15
6402 measured reflections	3 standard reflections every 97 reflections
6202 independent reflections	intensity decay: 4.9%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.0459P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.26 e Å^−3
6198 reflections	Δρmin = −0.39 e Å^−3
425 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2176 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (6)

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
S1	0.47843 (10)	0.26388 (7)	0.35937 (6)	0.03814 (19)
S2	0.17446 (11)	0.63415 (8)	0.98141 (7)	0.0428 (2)
O1	1.1353 (3)	0.8071 (2)	0.23113 (19)	0.0450 (5)
H1O	1.2057	0.7849	0.1767	0.054*
O2	0.6877 (4)	0.2786 (3)	0.3761 (2)	0.0601 (7)
O3	0.4482 (4)	0.1270 (2)	0.3299 (2)	0.0494 (6)
O4	0.3874 (4)	0.3755 (3)	0.28757 (19)	0.0517 (6)
O5	0.2942 (3)	0.7194 (2)	1.03578 (18)	0.0471 (6)
O6	0.0486 (4)	0.5535 (3)	1.0580 (3)	0.0736 (9)
O7	0.3024 (5)	0.5566 (3)	0.9030 (2)	0.0764 (9)
N1	0.9053 (4)	1.2983 (3)	0.1145 (2)	0.0421 (6)
N2	0.7345 (4)	0.6850 (2)	0.3182 (2)	0.0366 (6)
C1	0.7592 (5)	1.2270 (3)	0.0800 (2)	0.0345 (6)
C2	0.6122 (6)	1.2972 (4)	0.0166 (3)	0.0469 (8)
H2	0.6140	1.3923	−0.0040	0.056*
C3	0.4670 (6)	1.2255 (4)	−0.0147 (3)	0.0506 (9)
H3	0.3670	1.2722	−0.0559	0.061*
C4	0.4661 (5)	1.0809 (4)	0.0147 (3)	0.0478 (8)
H4	0.3658	1.0327	−0.0074	0.057*
C5	0.6090 (5)	1.0119 (3)	0.0746 (2)	0.0372 (7)
H5	0.6059	0.9163	0.0929	0.045*
C6	0.7638 (5)	1.0808 (3)	0.1106 (2)	0.0311 (6)
C7	0.9193 (4)	1.0165 (3)	0.1744 (2)	0.0326 (6)
C8	1.0588 (5)	1.0960 (3)	0.2049 (2)	0.0391 (7)
H8	1.1616	1.0544	0.2464	0.047*
C9	1.0472 (5)	1.2383 (3)	0.1742 (3)	0.0437 (8)
H9	1.1412	1.2919	0.1962	0.052*
C10	0.9337 (4)	0.8606 (3)	0.2070 (2)	0.0336 (6)
H10	0.8985	0.8110	0.1485	0.040*
C11	0.7770 (4)	0.8366 (3)	0.3034 (2)	0.0302 (6)
H11	0.6471	0.8940	0.2891	0.036*
C12	0.8387 (5)	0.8793 (3)	0.4085 (2)	0.0375 (7)
H12A	0.9841	0.8913	0.4015	0.045*
H12B	0.7602	0.9679	0.4267	0.045*
C13	0.7957 (5)	0.7645 (3)	0.4950 (2)	0.0403 (7)
H13	0.8211	0.7948	0.5636	0.048*
C14	0.5732 (5)	0.7302 (4)	0.4991 (3)	0.0448 (8)
H14	0.5565	0.6520	0.5525	0.054*
C15	0.5425 (5)	0.6792 (3)	0.3908 (3)	0.0416 (7)
H15A	0.5080	0.5833	0.4000	0.050*
H15B	0.4293	0.7383	0.3604	0.050*
C16	0.9390 (6)	0.6319 (4)	0.4702 (3)	0.0552 (9)
H16A	0.9112	0.5568	0.5235	0.066*
H16B	1.0810	0.6492	0.4716	0.066*
C17	0.9077 (6)	0.5873 (3)	0.3616 (3)	0.0479 (8)
H17A	1.0331	0.5918	0.3147	0.057*
H17B	0.8744	0.4912	0.3674	0.057*
C18	0.4096 (6)	0.8492 (5)	0.5265 (3)	0.0603 (10)
H18	0.4112	0.9332	0.4846	0.072*
C19	0.2669 (8)	0.8434 (7)	0.6040 (4)	0.0956 (17)
H19A	0.2607	0.7611	0.6476	0.115*
H19B	0.1706	0.9214	0.6163	0.115*
C20	0.4057 (5)	0.3533 (3)	0.5605 (3)	0.0459 (8)
H20	0.5385	0.3793	0.5509	0.055*
C21	0.2819 (6)	0.3798 (4)	0.6534 (3)	0.0533 (9)
H21	0.3335	0.4233	0.7058	0.064*
C22	0.0840 (6)	0.3432 (3)	0.6697 (3)	0.0525 (9)
C23	0.0134 (6)	0.2757 (4)	0.5911 (3)	0.0519 (9)
H23	−0.1182	0.2479	0.6010	0.062*
C24	0.1346 (5)	0.2489 (3)	0.4985 (3)	0.0417 (7)
H24	0.0837	0.2041	0.4465	0.050*
C25	0.3305 (5)	0.2881 (3)	0.4825 (2)	0.0368 (7)
C26	−0.0543 (9)	0.3810 (5)	0.7683 (4)	0.0882 (16)
H26A	−0.0753	0.4814	0.7713	0.106*
H26B	0.0095	0.3390	0.8297	0.106*
H26C	−0.1848	0.3464	0.7666	0.106*
C27	0.0573 (5)	0.8849 (3)	0.8753 (3)	0.0444 (8)
H27	0.1840	0.9102	0.8882	0.053*
C28	−0.0753 (6)	0.9765 (4)	0.8173 (3)	0.0483 (8)
H28	−0.0364	1.0638	0.7919	0.058*
C29	−0.2646 (5)	0.9418 (3)	0.7962 (3)	0.0414 (7)
C30	−0.3163 (5)	0.8120 (4)	0.8344 (3)	0.0480 (8)
H30	−0.4415	0.7857	0.8199	0.058*
C31	−0.1889 (5)	0.7196 (3)	0.8935 (3)	0.0435 (8)
H31	−0.2297	0.6332	0.9198	0.052*
C32	0.0000 (5)	0.7552 (3)	0.9138 (2)	0.0361 (7)
C33	−0.4060 (7)	1.0453 (4)	0.7338 (3)	0.0613 (10)
H33A	−0.3477	1.0553	0.6618	0.074*
H33B	−0.4224	1.1349	0.7639	0.074*
H33C	−0.5381	1.0115	0.7361	0.074*
O8	0.5883 (4)	0.5667 (3)	0.15909 (18)	0.0458 (5)
H1N	0.909 (9)	1.395 (6)	0.085 (5)	0.12 (2)*
H2N	0.685 (6)	0.657 (4)	0.253 (3)	0.064 (11)*
H0A	0.527 (6)	0.509 (4)	0.197 (3)	0.092 (12)*
H0B	0.508 (5)	0.608 (4)	0.118 (3)	0.092 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0337 (4)	0.0366 (4)	0.0455 (4)	−0.0064 (3)	−0.0059 (3)	−0.0052 (3)
S2	0.0451 (5)	0.0307 (4)	0.0525 (5)	−0.0003 (3)	−0.0105 (4)	−0.0007 (3)
O1	0.0356 (12)	0.0437 (13)	0.0527 (13)	0.0104 (10)	−0.0044 (10)	−0.0088 (11)
O2	0.0383 (13)	0.0718 (18)	0.0735 (18)	−0.0126 (12)	−0.0044 (12)	−0.0157 (14)
O3	0.0505 (14)	0.0423 (12)	0.0575 (14)	−0.0069 (10)	−0.0040 (11)	−0.0153 (11)
O4	0.0587 (15)	0.0480 (13)	0.0488 (13)	−0.0105 (11)	−0.0056 (12)	0.0022 (11)
O5	0.0440 (13)	0.0492 (13)	0.0481 (13)	−0.0026 (10)	−0.0112 (11)	0.0016 (11)
O6	0.0700 (18)	0.0528 (16)	0.101 (2)	−0.0305 (14)	−0.0237 (16)	0.0334 (15)
O7	0.081 (2)	0.0642 (18)	0.081 (2)	0.0317 (15)	−0.0231 (17)	−0.0302 (16)
N1	0.0542 (17)	0.0307 (13)	0.0417 (15)	−0.0108 (12)	0.0004 (13)	−0.0022 (11)
N2	0.0419 (14)	0.0261 (12)	0.0446 (15)	−0.0052 (10)	−0.0121 (12)	−0.0067 (11)
C1	0.0419 (16)	0.0292 (14)	0.0316 (15)	−0.0043 (12)	0.0027 (12)	−0.0055 (12)
C2	0.060 (2)	0.0364 (17)	0.0402 (18)	0.0069 (15)	−0.0039 (16)	−0.0011 (14)
C3	0.054 (2)	0.053 (2)	0.0434 (19)	0.0095 (16)	−0.0151 (16)	−0.0064 (16)
C4	0.0474 (19)	0.058 (2)	0.0403 (18)	−0.0059 (16)	−0.0107 (15)	−0.0099 (16)
C5	0.0407 (16)	0.0319 (15)	0.0410 (17)	−0.0078 (13)	−0.0070 (13)	−0.0042 (13)
C6	0.0338 (14)	0.0311 (14)	0.0278 (14)	−0.0019 (11)	0.0008 (11)	−0.0061 (11)
C7	0.0338 (15)	0.0300 (14)	0.0342 (15)	−0.0041 (11)	−0.0007 (12)	−0.0069 (12)
C8	0.0342 (16)	0.0417 (17)	0.0420 (17)	−0.0027 (13)	−0.0065 (13)	−0.0056 (14)
C9	0.0468 (18)	0.0413 (18)	0.0473 (19)	−0.0181 (15)	−0.0033 (15)	−0.0111 (15)
C10	0.0337 (15)	0.0299 (14)	0.0369 (16)	0.0002 (12)	−0.0043 (12)	−0.0060 (12)
C11	0.0314 (14)	0.0217 (12)	0.0384 (15)	−0.0013 (11)	−0.0085 (12)	−0.0050 (11)
C12	0.0409 (16)	0.0350 (16)	0.0392 (16)	−0.0100 (13)	−0.0035 (13)	−0.0105 (13)
C13	0.0491 (18)	0.0409 (16)	0.0339 (16)	−0.0087 (14)	−0.0140 (13)	−0.0026 (13)
C14	0.058 (2)	0.0421 (17)	0.0372 (17)	−0.0157 (15)	−0.0076 (15)	−0.0005 (14)
C15	0.0457 (17)	0.0361 (16)	0.0449 (18)	−0.0102 (13)	−0.0066 (14)	−0.0038 (13)
C16	0.061 (2)	0.0427 (18)	0.064 (2)	−0.0009 (16)	−0.0270 (19)	0.0053 (16)
C17	0.058 (2)	0.0223 (14)	0.062 (2)	0.0040 (14)	−0.0154 (17)	0.0002 (14)
C18	0.052 (2)	0.070 (3)	0.065 (2)	−0.0170 (18)	0.0024 (19)	−0.029 (2)
C19	0.073 (3)	0.130 (5)	0.091 (4)	−0.019 (3)	0.009 (3)	−0.056 (3)
C20	0.0477 (18)	0.0420 (18)	0.0500 (19)	−0.0038 (14)	−0.0187 (15)	−0.0008 (15)
C21	0.077 (3)	0.0454 (19)	0.0392 (18)	−0.0060 (18)	−0.0161 (18)	−0.0029 (15)
C22	0.071 (2)	0.0345 (17)	0.047 (2)	0.0030 (16)	0.0038 (17)	−0.0004 (15)
C23	0.048 (2)	0.0401 (18)	0.066 (2)	−0.0050 (15)	0.0011 (17)	−0.0056 (17)
C24	0.0444 (18)	0.0348 (16)	0.0469 (18)	−0.0057 (13)	−0.0060 (15)	−0.0048 (14)
C25	0.0405 (16)	0.0289 (15)	0.0415 (17)	−0.0014 (12)	−0.0108 (13)	−0.0022 (12)
C26	0.117 (4)	0.076 (3)	0.066 (3)	−0.002 (3)	0.019 (3)	−0.019 (2)
C27	0.0487 (19)	0.0363 (17)	0.0503 (19)	−0.0135 (14)	−0.0081 (15)	0.0013 (14)
C28	0.057 (2)	0.0382 (17)	0.050 (2)	−0.0119 (15)	−0.0079 (16)	0.0061 (15)
C29	0.0445 (18)	0.0410 (17)	0.0383 (17)	0.0006 (14)	−0.0065 (14)	−0.0058 (13)
C30	0.0416 (18)	0.0431 (18)	0.062 (2)	−0.0068 (14)	−0.0110 (16)	−0.0119 (16)
C31	0.0392 (17)	0.0311 (16)	0.061 (2)	−0.0072 (13)	−0.0040 (15)	−0.0017 (14)
C32	0.0412 (16)	0.0295 (15)	0.0374 (17)	−0.0004 (12)	−0.0035 (13)	−0.0068 (12)
C33	0.069 (2)	0.056 (2)	0.059 (2)	0.0010 (19)	−0.0218 (19)	0.0001 (18)
O8	0.0472 (13)	0.0493 (14)	0.0449 (13)	−0.0141 (11)	−0.0135 (10)	−0.0029 (11)

Geometric parameters (Å, º)

S1—O2	1.438 (3)	C14—C15	1.543 (4)
S1—O3	1.439 (2)	C14—H14	0.9800
S1—O4	1.460 (3)	C15—H15A	0.9700
S1—C25	1.775 (3)	C15—H15B	0.9700
S2—O7	1.432 (3)	C16—C17	1.524 (5)
S2—O6	1.451 (3)	C16—H16A	0.9700
S2—O5	1.462 (2)	C16—H16B	0.9700
S2—C32	1.762 (3)	C17—H17A	0.9700
O1—C10	1.413 (4)	C17—H17B	0.9700
O1—H1O	0.8200	C18—C19	1.293 (6)
N1—C9	1.310 (5)	C18—H18	0.9300
N1—C1	1.373 (4)	C19—H19A	0.9300
N1—H1N	0.98 (6)	C19—H19B	0.9300
N2—C15	1.489 (4)	C20—C25	1.382 (4)
N2—C17	1.500 (4)	C20—C21	1.388 (5)
N2—C11	1.509 (4)	C20—H20	0.9300
N2—H2N	0.99 (4)	C21—C22	1.379 (6)
C1—C2	1.395 (4)	C21—H21	0.9300
C1—C6	1.422 (4)	C22—C23	1.385 (5)
C2—C3	1.353 (5)	C22—C26	1.514 (6)
C2—H2	0.9300	C23—C24	1.377 (5)
C3—C4	1.409 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.376 (4)
C4—C5	1.344 (5)	C24—H24	0.9300
C4—H4	0.9300	C26—H26A	0.9600
C5—C6	1.413 (4)	C26—H26B	0.9600
C5—H5	0.9300	C26—H26C	0.9600
C6—C7	1.419 (4)	C27—C28	1.381 (5)
C7—C8	1.369 (4)	C27—C32	1.383 (4)
C7—C10	1.514 (4)	C27—H27	0.9300
C8—C9	1.384 (4)	C28—C29	1.385 (5)
C8—H8	0.9300	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.370 (5)
C10—C11	1.540 (4)	C29—C33	1.506 (5)
C10—H10	0.9800	C30—C31	1.373 (5)
C11—C12	1.540 (4)	C30—H30	0.9300
C11—H11	0.9800	C31—C32	1.382 (4)
C12—C13	1.524 (4)	C31—H31	0.9300
C12—H12A	0.9700	C33—H33A	0.9600
C12—H12B	0.9700	C33—H33B	0.9600
C13—C16	1.519 (5)	C33—H33C	0.9600
C13—C14	1.533 (5)	O8—H0A	0.823 (10)
C13—H13	0.9800	O8—H0B	0.829 (10)
C14—C18	1.502 (5)
O2—S1—O3	114.45 (15)	C18—C14—H14	107.9
O2—S1—O4	113.09 (16)	C13—C14—H14	107.9
O3—S1—O4	111.37 (15)	C15—C14—H14	107.9
O2—S1—C25	106.39 (15)	N2—C15—C14	110.0 (3)
O3—S1—C25	106.34 (15)	N2—C15—H15A	109.7
O4—S1—C25	104.29 (14)	C14—C15—H15A	109.7
O7—S2—O6	116.4 (2)	N2—C15—H15B	109.7
O7—S2—O5	111.29 (17)	C14—C15—H15B	109.7
O6—S2—O5	110.07 (16)	H15A—C15—H15B	108.2
O7—S2—C32	106.87 (16)	C13—C16—C17	110.3 (3)
O6—S2—C32	105.82 (16)	C13—C16—H16A	109.6
O5—S2—C32	105.61 (14)	C17—C16—H16A	109.6
C10—O1—H1O	109.5	C13—C16—H16B	109.6
C9—N1—C1	123.2 (3)	C17—C16—H16B	109.6
C9—N1—H1N	120 (3)	H16A—C16—H16B	108.1
C1—N1—H1N	116 (3)	N2—C17—C16	108.4 (3)
C15—N2—C17	110.0 (3)	N2—C17—H17A	110.0
C15—N2—C11	107.6 (2)	C16—C17—H17A	110.0
C17—N2—C11	113.4 (2)	N2—C17—H17B	110.0
C15—N2—H2N	99 (2)	C16—C17—H17B	110.0
C17—N2—H2N	116 (2)	H17A—C17—H17B	108.4
C11—N2—H2N	110 (2)	C19—C18—C14	124.7 (5)
N1—C1—C2	120.3 (3)	C19—C18—H18	117.6
N1—C1—C6	118.0 (3)	C14—C18—H18	117.6
C2—C1—C6	121.7 (3)	C18—C19—H19A	120.0
C3—C2—C1	119.3 (3)	C18—C19—H19B	120.0
C3—C2—H2	120.3	H19A—C19—H19B	120.0
C1—C2—H2	120.3	C25—C20—C21	119.6 (3)
C2—C3—C4	120.5 (3)	C25—C20—H20	120.2
C2—C3—H3	119.7	C21—C20—H20	120.2
C4—C3—H3	119.7	C22—C21—C20	121.6 (3)
C5—C4—C3	120.6 (3)	C22—C21—H21	119.2
C5—C4—H4	119.7	C20—C21—H21	119.2
C3—C4—H4	119.7	C21—C22—C23	117.8 (3)
C4—C5—C6	121.7 (3)	C21—C22—C26	121.0 (4)
C4—C5—H5	119.1	C23—C22—C26	121.1 (4)
C6—C5—H5	119.1	C24—C23—C22	121.3 (3)
C5—C6—C7	125.4 (3)	C24—C23—H23	119.4
C5—C6—C1	116.2 (3)	C22—C23—H23	119.4
C7—C6—C1	118.4 (3)	C25—C24—C23	120.4 (3)
C8—C7—C6	119.5 (3)	C25—C24—H24	119.8
C8—C7—C10	120.0 (3)	C23—C24—H24	119.8
C6—C7—C10	120.4 (2)	C24—C25—C20	119.5 (3)
C7—C8—C9	120.1 (3)	C24—C25—S1	119.9 (2)
C7—C8—H8	119.9	C20—C25—S1	120.5 (3)
C9—C8—H8	119.9	C22—C26—H26A	109.5
N1—C9—C8	120.8 (3)	C22—C26—H26B	109.5
N1—C9—H9	119.6	H26A—C26—H26B	109.5
C8—C9—H9	119.6	C22—C26—H26C	109.5
O1—C10—C7	111.1 (2)	H26A—C26—H26C	109.5
O1—C10—C11	110.5 (2)	H26B—C26—H26C	109.5
C7—C10—C11	109.0 (2)	C28—C27—C32	119.4 (3)
O1—C10—H10	108.8	C28—C27—H27	120.3
C7—C10—H10	108.8	C32—C27—H27	120.3
C11—C10—H10	108.8	C27—C28—C29	121.7 (3)
N2—C11—C10	111.3 (2)	C27—C28—H28	119.1
N2—C11—C12	108.3 (2)	C29—C28—H28	119.1
C10—C11—C12	114.8 (2)	C30—C29—C28	117.5 (3)
N2—C11—H11	107.4	C30—C29—C33	122.3 (3)
C10—C11—H11	107.4	C28—C29—C33	120.2 (3)
C12—C11—H11	107.4	C29—C30—C31	122.0 (3)
C13—C12—C11	109.0 (2)	C29—C30—H30	119.0
C13—C12—H12A	109.9	C31—C30—H30	119.0
C11—C12—H12A	109.9	C30—C31—C32	119.9 (3)
C13—C12—H12B	109.9	C30—C31—H31	120.0
C11—C12—H12B	109.9	C32—C31—H31	120.0
H12A—C12—H12B	108.3	C31—C32—C27	119.3 (3)
C16—C13—C12	108.4 (3)	C31—C32—S2	121.0 (2)
C16—C13—C14	108.0 (3)	C27—C32—S2	119.6 (2)
C12—C13—C14	111.2 (3)	C29—C33—H33A	109.5
C16—C13—H13	109.7	C29—C33—H33B	109.5
C12—C13—H13	109.7	H33A—C33—H33B	109.5
C14—C13—H13	109.7	C29—C33—H33C	109.5
C18—C14—C13	115.2 (3)	H33A—C33—H33C	109.5
C18—C14—C15	109.8 (3)	H33B—C33—H33C	109.5
C13—C14—C15	107.9 (3)	H0A—O8—H0B	108.0 (17)
C9—N1—C1—C2	180.0 (3)	C11—N2—C15—C14	−61.4 (3)
C9—N1—C1—C6	−0.3 (4)	C18—C14—C15—N2	124.3 (3)
N1—C1—C2—C3	−178.6 (3)	C13—C14—C15—N2	−2.0 (3)
C6—C1—C2—C3	1.6 (5)	C12—C13—C16—C17	−57.7 (4)
C1—C2—C3—C4	−1.2 (5)	C14—C13—C16—C17	62.9 (4)
C2—C3—C4—C5	0.2 (5)	C15—N2—C17—C16	−59.1 (3)
C3—C4—C5—C6	0.3 (5)	C11—N2—C17—C16	61.5 (4)
C4—C5—C6—C7	179.6 (3)	C13—C16—C17—N2	−3.7 (4)
C4—C5—C6—C1	0.2 (4)	C13—C14—C18—C19	−124.1 (4)
N1—C1—C6—C5	179.2 (3)	C15—C14—C18—C19	113.9 (4)
C2—C1—C6—C5	−1.1 (4)	C25—C20—C21—C22	−0.3 (5)
N1—C1—C6—C7	−0.3 (4)	C20—C21—C22—C23	1.4 (5)
C2—C1—C6—C7	179.4 (3)	C20—C21—C22—C26	−176.1 (4)
C5—C6—C7—C8	−179.2 (3)	C21—C22—C23—C24	−1.5 (5)
C1—C6—C7—C8	0.2 (4)	C26—C22—C23—C24	176.0 (4)
C5—C6—C7—C10	1.9 (4)	C22—C23—C24—C25	0.5 (5)
C1—C6—C7—C10	−178.6 (2)	C23—C24—C25—C20	0.7 (4)
C6—C7—C8—C9	0.4 (4)	C23—C24—C25—S1	−175.7 (3)
C10—C7—C8—C9	179.3 (3)	C21—C20—C25—C24	−0.8 (5)
C1—N1—C9—C8	1.0 (5)	C21—C20—C25—S1	175.6 (2)
C7—C8—C9—N1	−1.0 (5)	O2—S1—C25—C24	−165.1 (2)
C8—C7—C10—O1	−22.6 (4)	O3—S1—C25—C24	−42.7 (3)
C6—C7—C10—O1	156.2 (2)	O4—S1—C25—C24	75.1 (3)
C8—C7—C10—C11	99.3 (3)	O2—S1—C25—C20	18.5 (3)
C6—C7—C10—C11	−81.8 (3)	O3—S1—C25—C20	140.9 (2)
C15—N2—C11—C10	−164.0 (2)	O4—S1—C25—C20	−101.3 (3)
C17—N2—C11—C10	74.1 (3)	C32—C27—C28—C29	−0.3 (5)
C15—N2—C11—C12	68.9 (3)	C27—C28—C29—C30	−0.4 (5)
C17—N2—C11—C12	−53.0 (3)	C27—C28—C29—C33	179.3 (3)
O1—C10—C11—N2	−75.9 (3)	C28—C29—C30—C31	1.3 (5)
C7—C10—C11—N2	161.8 (2)	C33—C29—C30—C31	−178.3 (3)
O1—C10—C11—C12	47.6 (3)	C29—C30—C31—C32	−1.6 (5)
C7—C10—C11—C12	−74.7 (3)	C30—C31—C32—C27	0.8 (5)
N2—C11—C12—C13	−10.7 (3)	C30—C31—C32—S2	−175.5 (3)
C10—C11—C12—C13	−135.8 (3)	C28—C27—C32—C31	0.1 (5)
C11—C12—C13—C16	65.9 (3)	C28—C27—C32—S2	176.5 (3)
C11—C12—C13—C14	−52.6 (3)	O7—S2—C32—C31	90.1 (3)
C16—C13—C14—C18	178.1 (3)	O6—S2—C32—C31	−34.6 (3)
C12—C13—C14—C18	−63.1 (4)	O5—S2—C32—C31	−151.3 (2)
C16—C13—C14—C15	−58.8 (3)	O7—S2—C32—C27	−86.3 (3)
C12—C13—C14—C15	60.0 (3)	O6—S2—C32—C27	149.1 (3)
C17—N2—C15—C14	62.6 (3)	O5—S2—C32—C27	32.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6^i	0.98 (6)	1.86 (6)	2.749 (4)	150 (5)
N2—H2N···O8	0.99 (4)	1.75 (4)	2.718 (3)	164 (4)
O1—H1O···O5^ii	0.82	1.96	2.754 (3)	163
O8—H0A···O4	0.82 (1)	1.91 (1)	2.731 (4)	179 (5)
O8—H0B···O5^iii	0.83 (1)	1.98 (1)	2.806 (3)	172 (4)
C8—H8···O3^iv	0.93	2.46	3.205 (4)	138
C9—H9···O4^iv	0.93	2.34	3.247 (4)	164
C11—H11···O3^v	0.98	2.51	3.320 (4)	140
C17—H17A···O1	0.97	2.39	3.026 (4)	123
C17—H17B···O2	0.97	2.50	3.441 (3)	164

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