2-(4-Methoxy­styr­yl)-1-methyl­pyridinium 4-chloro­benzene­sulfonate

There are two crystallographically independent ion pairs in the asymmetric unit of the title compound, C₁₅H₁₆NO⁺·C₆H₄ClO₃S⁻. Both cations adopt an E configuration with respect to the C=C bond. The dihedral angle between the pyridinium and benzene rings of the two cations are 6.0 (3) and 2.6 (2)°. In the crystal structure, independent cations and anions are individually linked into alternate layers parallel to the ab plane via weak C—H...O inter­actions; these layers are inter­connected through weak intra- and inter­molecular C—H...O inter­actions, forming a three-dimensional network. C—H...π inter­actions involving the benzene and pyridinium rings also help to stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.069
• wR factor = 0.200
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      1.538
            Test value =      1.275
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.05
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       1.54 e/A   
PLAT213_ALERT_2_C Atom O6#     has ADP max/min Ratio .............       3.50 prola
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        S1B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        S1A
PLAT245_ALERT_2_C U(iso) H15C    Smaller than U(eq) C15A    by ...       0.01 AngSq
PLAT245_ALERT_2_C U(iso) H15E    Smaller than U(eq) C15B    by ...       0.01 AngSq
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1A   ..  O3A     ..       3.17 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1B   ..  O3BB    ..       3.05 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1B   ..  O3BA    ..       3.25 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H16 N O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  17 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
  12 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-(4-Methoxystyryl)-1-methylpyridinium 4-chlorobenzenesulfonate

Crystal data

C15H16NO^+·C6H4ClO3S^−	F(000) = 1744
Mr = 417.91	Dx = 1.440 Mg m^−3
Monoclinic, P21/c	Melting point = 470–471 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2016 (5) Å	Cell parameters from 7521 reflections
b = 13.7923 (4) Å	θ = 1.6–26.0°
c = 22.0003 (7) Å	µ = 0.34 mm^−1
β = 123.274 (2)°	T = 100 K
V = 3856.5 (2) Å^3	Needle, yellow
Z = 8	0.56 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	7521 independent reflections
Radiation source: fine-focus sealed tube	5951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→17
Tmin = 0.836, Tmax = 0.947	l = −27→27
47660 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0999P)^2 + 9.2696P] where P = (Fo^2 + 2Fc^2)/3
7521 reflections	(Δ/σ)max = 0.001
563 parameters	Δρmax = 1.54 e Å^−3
18 restraints	Δρmin = −0.75 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)
S1A	0.74122 (6)	0.53963 (6)	0.74950 (5)	0.0232 (2)
Cl1A	0.99232 (9)	0.85893 (7)	0.70408 (5)	0.0407 (3)
O1A	−0.1752 (2)	1.3836 (2)	0.02739 (13)	0.0388 (7)
O2A	0.7049 (2)	0.5861 (2)	0.79108 (17)	0.0428 (7)
O3A	0.8170 (2)	0.4641 (2)	0.78949 (17)	0.0439 (7)
O4A	0.6564 (3)	0.5082 (2)	0.67841 (16)	0.0513 (8)
N1A	−0.1479 (3)	0.7638 (2)	−0.05484 (17)	0.0335 (7)
C1A	−0.1286 (4)	0.6664 (3)	−0.0488 (2)	0.0411 (10)
H1A	−0.1746	0.6256	−0.0869	0.049*
C2A	−0.0429 (4)	0.6280 (3)	0.0121 (3)	0.0462 (11)
H2A	−0.0310	0.5614	0.0157	0.055*
C3A	0.0260 (4)	0.6882 (3)	0.0684 (3)	0.0454 (10)
H3A	0.0848	0.6629	0.1102	0.054*
C4A	0.0068 (3)	0.7857 (3)	0.0621 (2)	0.0398 (10)
H4A	0.0539	0.8265	0.0998	0.048*
C5A	−0.0820 (3)	0.8255 (3)	0.0005 (2)	0.0348 (9)
C6A	−0.1123 (3)	0.9255 (3)	−0.0086 (2)	0.0382 (9)
H6A	−0.1665	0.9466	−0.0543	0.046*
C7A	−0.0659 (3)	0.9901 (3)	0.0461 (2)	0.0367 (9)
H7A	−0.0121	0.9675	0.0914	0.044*
C8A	−0.0929 (3)	1.0930 (3)	0.04017 (19)	0.0314 (8)
C9A	−0.1851 (3)	1.1323 (3)	−0.02010 (19)	0.0312 (8)
H9A	−0.2300	1.0923	−0.0592	0.037*
C10A	−0.2102 (3)	1.2282 (3)	−0.02254 (18)	0.0315 (8)
H10A	−0.2719	1.2525	−0.0628	0.040 (12)*
C11A	−0.1437 (3)	1.2896 (3)	0.03504 (18)	0.0281 (8)
C12A	−0.0512 (3)	1.2537 (3)	0.09550 (18)	0.0288 (8)
H12A	−0.0060	1.2944	0.1340	0.040 (12)*
C13A	−0.0278 (3)	1.1565 (3)	0.09709 (18)	0.0283 (8)
H13A	0.0336	1.1323	0.1377	0.031 (10)*
C14A	−0.1189 (3)	1.4458 (3)	0.0895 (2)	0.0391 (9)
H14A	−0.1497	1.5093	0.0772	0.037 (11)*
H14B	−0.0467	1.4498	0.1044	0.049 (13)*
H14C	−0.1226	1.4198	0.1286	0.047 (13)*
C15A	−0.2420 (3)	0.8002 (3)	−0.1219 (2)	0.0371 (9)
H15A	−0.2871	0.8321	−0.1103	0.045 (12)*
H15B	−0.2790	0.7469	−0.1541	0.058 (14)*
H15C	−0.2213	0.8453	−0.1451	0.026 (10)*
C16A	0.8089 (2)	0.6303 (2)	0.73332 (16)	0.0192 (6)
C17A	0.7798 (3)	0.7271 (2)	0.72692 (17)	0.0235 (7)
H17A	0.7232	0.7442	0.7300	0.040 (12)*
C18A	0.8339 (3)	0.7977 (2)	0.71629 (17)	0.0268 (8)
H18A	0.8139	0.8624	0.7115	0.028 (10)*
C19A	0.9179 (3)	0.7702 (2)	0.71255 (17)	0.0259 (7)
C20A	0.9479 (3)	0.6739 (2)	0.71674 (16)	0.0220 (7)
H20A	1.0037	0.6572	0.7127	0.024 (9)*
C21A	0.8921 (2)	0.6039 (2)	0.72698 (17)	0.0200 (7)
H21A	0.9102	0.5389	0.7297	0.024 (9)*
S1B	0.24499 (6)	0.94356 (6)	0.24253 (5)	0.0263 (2)
Cl1B	0.53089 (8)	0.64984 (6)	0.20871 (5)	0.0317 (2)
O1B	0.6735 (2)	0.8972 (2)	0.47042 (13)	0.0372 (6)
O2BA	0.1743 (8)	0.8841 (6)	0.2494 (10)	0.026 (3)	0.65 (6)
O3BA	0.3243 (9)	0.9936 (8)	0.3091 (6)	0.028 (2)	0.65 (6)
O4BA	0.1949 (9)	1.0047 (8)	0.1774 (6)	0.030 (3)	0.65 (6)
O2BB	0.194 (3)	0.895 (3)	0.278 (3)	0.060 (7)	0.35 (6)
O3BB	0.308 (3)	1.017 (4)	0.290 (3)	0.073 (10)	0.35 (6)
O4BB	0.171 (4)	0.988 (3)	0.1778 (15)	0.077 (8)	0.35 (6)
N1B	0.6683 (3)	0.2791 (2)	0.57215 (18)	0.0341 (7)
C1B	0.6496 (3)	0.1830 (3)	0.5704 (2)	0.0410 (10)
H1B	0.6962	0.1447	0.6101	0.049*
C2B	0.5644 (4)	0.1411 (4)	0.5118 (3)	0.0500 (11)
H2B	0.5531	0.0747	0.5111	0.060*
C3B	0.4947 (4)	0.1982 (4)	0.4531 (3)	0.0519 (12)
H3B	0.4357	0.1707	0.4127	0.062*
C4B	0.5135 (3)	0.2963 (4)	0.4550 (2)	0.0430 (10)
H4B	0.4663	0.3350	0.4158	0.052*
C5B	0.6025 (3)	0.3382 (3)	0.5152 (2)	0.0362 (9)
C6B	0.6305 (3)	0.4397 (3)	0.5204 (2)	0.0379 (9)
H6B	0.6847	0.4633	0.5652	0.045*
C7B	0.5823 (3)	0.5015 (3)	0.4640 (2)	0.0380 (9)
H7B	0.5288	0.4763	0.4196	0.046*
C8B	0.6062 (3)	0.6042 (3)	0.46605 (19)	0.0328 (8)
C9B	0.6964 (3)	0.6480 (3)	0.52469 (19)	0.0348 (9)
H9B	0.7436	0.6105	0.5648	0.042*
C10B	0.7163 (3)	0.7446 (3)	0.52416 (19)	0.0344 (9)
H10B	0.7766	0.7720	0.5636	0.047 (13)*
C11B	0.6469 (3)	0.8019 (3)	0.46507 (18)	0.0302 (8)
C12B	0.5564 (3)	0.7614 (3)	0.40565 (18)	0.0292 (8)
H12B	0.5095	0.7995	0.3659	0.047 (13)*
C13B	0.5373 (3)	0.6633 (3)	0.40685 (18)	0.0297 (8)
H13B	0.4772	0.6360	0.3671	0.030 (10)*
C14B	0.6112 (3)	0.9589 (3)	0.40879 (19)	0.0349 (9)
H14D	0.6400	1.0232	0.4201	0.050 (13)*
H14E	0.5402	0.9604	0.3968	0.049 (13)*
H14F	0.6116	0.9343	0.3681	0.028 (10)*
C15B	0.7638 (3)	0.3176 (3)	0.6382 (2)	0.0381 (9)
H15D	0.8027	0.2652	0.6708	0.048 (13)*
H15E	0.7439	0.3629	0.6618	0.027 (10)*
H15F	0.8069	0.3499	0.6249	0.044 (12)*
C16B	0.3204 (2)	0.8590 (2)	0.22814 (17)	0.0220 (7)
C17B	0.3022 (3)	0.7599 (2)	0.22535 (17)	0.0254 (7)
H17B	0.2477	0.7367	0.2288	0.036 (11)*
C18B	0.3653 (3)	0.6955 (2)	0.21722 (17)	0.0247 (7)
H18B	0.3527	0.6292	0.2146	0.017 (8)*
C19B	0.4466 (3)	0.7306 (2)	0.21328 (17)	0.0237 (7)
C20B	0.4645 (3)	0.8299 (2)	0.21383 (17)	0.0224 (7)
H20B	0.5181	0.8529	0.2092	0.041 (12)*
C21B	0.4003 (2)	0.8935 (2)	0.22133 (17)	0.0217 (7)
H21B	0.4110	0.9600	0.2218	0.026 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0167 (4)	0.0222 (4)	0.0286 (4)	−0.0017 (3)	0.0111 (4)	−0.0039 (3)
Cl1A	0.0565 (6)	0.0275 (5)	0.0310 (5)	−0.0199 (4)	0.0196 (5)	−0.0012 (4)
O1A	0.0395 (15)	0.0365 (15)	0.0221 (13)	0.0036 (12)	0.0052 (12)	0.0053 (11)
O2A	0.0429 (16)	0.0388 (16)	0.065 (2)	−0.0076 (13)	0.0417 (16)	−0.0125 (14)
O3A	0.0359 (15)	0.0373 (16)	0.066 (2)	0.0091 (12)	0.0327 (15)	0.0244 (14)
O4A	0.0491 (18)	0.0525 (19)	0.0359 (16)	−0.0301 (15)	0.0128 (14)	−0.0082 (14)
N1A	0.0335 (17)	0.0403 (19)	0.0357 (17)	−0.0044 (14)	0.0247 (15)	−0.0049 (14)
C1A	0.050 (3)	0.037 (2)	0.054 (3)	−0.0098 (19)	0.040 (2)	−0.0092 (19)
C2A	0.048 (3)	0.042 (2)	0.059 (3)	0.005 (2)	0.035 (2)	0.008 (2)
C3A	0.041 (2)	0.053 (3)	0.053 (3)	0.006 (2)	0.033 (2)	0.009 (2)
C4A	0.036 (2)	0.054 (3)	0.035 (2)	0.0011 (19)	0.0234 (19)	−0.0015 (19)
C5A	0.039 (2)	0.041 (2)	0.036 (2)	−0.0033 (17)	0.0279 (19)	−0.0063 (17)
C6A	0.040 (2)	0.044 (2)	0.032 (2)	−0.0075 (18)	0.0207 (18)	−0.0051 (17)
C7A	0.035 (2)	0.046 (2)	0.032 (2)	−0.0030 (18)	0.0196 (18)	−0.0033 (17)
C8A	0.0317 (19)	0.043 (2)	0.0219 (17)	−0.0011 (16)	0.0162 (16)	−0.0024 (15)
C9A	0.0295 (19)	0.043 (2)	0.0189 (17)	−0.0081 (16)	0.0121 (15)	−0.0058 (15)
C10A	0.0216 (17)	0.049 (2)	0.0153 (16)	−0.0019 (16)	0.0045 (14)	0.0062 (15)
C11A	0.0294 (19)	0.0306 (19)	0.0215 (17)	−0.0022 (15)	0.0121 (15)	0.0048 (14)
C12A	0.0254 (18)	0.040 (2)	0.0163 (16)	−0.0081 (16)	0.0088 (14)	−0.0021 (15)
C13A	0.0229 (17)	0.043 (2)	0.0171 (16)	−0.0012 (15)	0.0096 (14)	−0.0014 (15)
C14A	0.044 (2)	0.029 (2)	0.034 (2)	0.0016 (17)	0.0157 (19)	0.0010 (17)
C15A	0.041 (2)	0.042 (2)	0.037 (2)	−0.0063 (18)	0.0268 (19)	−0.0099 (18)
C16A	0.0151 (15)	0.0197 (16)	0.0153 (14)	−0.0003 (12)	0.0036 (12)	−0.0026 (12)
C17A	0.0235 (17)	0.0213 (17)	0.0188 (16)	0.0058 (13)	0.0072 (14)	−0.0029 (13)
C18A	0.037 (2)	0.0149 (16)	0.0158 (15)	0.0058 (14)	0.0066 (14)	−0.0005 (12)
C19A	0.0307 (18)	0.0204 (17)	0.0129 (15)	−0.0087 (14)	0.0033 (14)	0.0000 (12)
C20A	0.0189 (16)	0.0232 (16)	0.0173 (15)	−0.0013 (13)	0.0057 (13)	0.0000 (13)
C21A	0.0158 (15)	0.0148 (15)	0.0210 (15)	0.0020 (12)	0.0049 (13)	−0.0005 (12)
S1B	0.0190 (4)	0.0228 (4)	0.0345 (5)	0.0011 (3)	0.0130 (4)	0.0068 (4)
Cl1B	0.0403 (5)	0.0220 (4)	0.0333 (5)	0.0037 (4)	0.0206 (4)	0.0001 (3)
O1B	0.0316 (14)	0.0447 (16)	0.0203 (13)	−0.0022 (12)	0.0046 (11)	−0.0057 (11)
O2BA	0.020 (3)	0.021 (3)	0.045 (5)	−0.0002 (19)	0.023 (4)	0.003 (3)
O3BA	0.017 (3)	0.030 (4)	0.029 (4)	0.003 (2)	0.008 (3)	−0.008 (2)
O4BA	0.030 (4)	0.024 (3)	0.032 (4)	0.008 (3)	0.015 (3)	0.011 (3)
O2BB	0.045 (11)	0.083 (12)	0.07 (2)	0.019 (9)	0.044 (13)	0.035 (12)
O3BB	0.046 (11)	0.085 (19)	0.10 (2)	0.003 (12)	0.046 (14)	−0.037 (16)
O4BB	0.087 (18)	0.061 (13)	0.093 (13)	0.054 (12)	0.055 (12)	0.058 (10)
N1B	0.0349 (17)	0.0407 (19)	0.0369 (18)	0.0053 (14)	0.0261 (15)	0.0052 (14)
C1B	0.042 (2)	0.042 (2)	0.053 (3)	0.0030 (19)	0.035 (2)	−0.001 (2)
C2B	0.058 (3)	0.046 (3)	0.064 (3)	−0.004 (2)	0.045 (3)	−0.004 (2)
C3B	0.047 (3)	0.075 (3)	0.049 (3)	−0.018 (2)	0.036 (2)	−0.015 (2)
C4B	0.041 (2)	0.064 (3)	0.036 (2)	−0.001 (2)	0.029 (2)	0.002 (2)
C5B	0.035 (2)	0.050 (2)	0.032 (2)	0.0050 (18)	0.0240 (18)	0.0044 (18)
C6B	0.035 (2)	0.053 (3)	0.0272 (19)	0.0084 (19)	0.0181 (17)	0.0057 (18)
C7B	0.034 (2)	0.055 (3)	0.027 (2)	0.0026 (19)	0.0185 (18)	0.0020 (18)
C8B	0.032 (2)	0.046 (2)	0.0216 (17)	0.0059 (17)	0.0152 (16)	0.0055 (16)
C9B	0.0275 (19)	0.056 (3)	0.0180 (17)	0.0104 (18)	0.0106 (15)	0.0083 (16)
C10B	0.0215 (18)	0.057 (3)	0.0171 (17)	0.0009 (17)	0.0059 (15)	−0.0037 (16)
C11B	0.0242 (18)	0.048 (2)	0.0166 (16)	0.0014 (16)	0.0098 (15)	−0.0037 (15)
C12B	0.0236 (17)	0.044 (2)	0.0146 (16)	0.0030 (16)	0.0072 (14)	−0.0004 (15)
C13B	0.0227 (17)	0.047 (2)	0.0174 (16)	0.0001 (16)	0.0098 (15)	−0.0009 (15)
C14B	0.034 (2)	0.039 (2)	0.0249 (18)	−0.0006 (17)	0.0120 (16)	−0.0054 (16)
C15B	0.038 (2)	0.042 (2)	0.037 (2)	0.0047 (18)	0.0227 (19)	0.0059 (18)
C16B	0.0160 (15)	0.0217 (16)	0.0192 (15)	0.0000 (12)	0.0039 (13)	0.0055 (13)
C17B	0.0227 (17)	0.0263 (18)	0.0173 (15)	−0.0074 (14)	0.0046 (13)	0.0044 (13)
C18B	0.0309 (18)	0.0170 (16)	0.0171 (15)	−0.0056 (14)	0.0073 (14)	−0.0004 (12)
C19B	0.0264 (17)	0.0218 (16)	0.0167 (15)	0.0018 (13)	0.0079 (14)	0.0001 (13)
C20B	0.0210 (16)	0.0194 (16)	0.0204 (16)	−0.0023 (13)	0.0073 (14)	0.0012 (13)
C21B	0.0194 (16)	0.0172 (16)	0.0216 (16)	−0.0039 (12)	0.0068 (13)	0.0008 (12)

Geometric parameters (Å, º)

S1A—O3A	1.440 (3)	S1B—O2BA	1.425 (10)
S1A—O4A	1.444 (3)	S1B—O3BA	1.462 (11)
S1A—O2A	1.452 (3)	S1B—O4BA	1.465 (12)
S1A—C16A	1.775 (3)	S1B—O2BB	1.53 (2)
Cl1A—C19A	1.744 (3)	S1B—C16B	1.782 (3)
O1A—C11A	1.361 (5)	Cl1B—C19B	1.742 (3)
O1A—C14A	1.433 (5)	O1B—C11B	1.361 (5)
N1A—C1A	1.366 (5)	O1B—C14B	1.432 (5)
N1A—C5A	1.368 (5)	N1B—C1B	1.353 (5)
N1A—C15A	1.469 (5)	N1B—C5B	1.364 (5)
C1A—C2A	1.363 (6)	N1B—C15B	1.479 (5)
C1A—H1A	0.9300	C1B—C2B	1.357 (6)
C2A—C3A	1.378 (7)	C1B—H1B	0.9300
C2A—H2A	0.9300	C2B—C3B	1.381 (7)
C3A—C4A	1.366 (6)	C2B—H2B	0.9300
C3A—H3A	0.9300	C3B—C4B	1.379 (7)
C4A—C5A	1.398 (6)	C3B—H3B	0.9300
C4A—H4A	0.9300	C4B—C5B	1.397 (6)
C5A—C6A	1.433 (6)	C4B—H4B	0.9300
C6A—C7A	1.344 (6)	C5B—C6B	1.449 (6)
C6A—H6A	0.9300	C6B—C7B	1.343 (6)
C7A—C8A	1.464 (6)	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—C8B	1.457 (6)
C8A—C13A	1.398 (5)	C7B—H7B	0.9300
C8A—C9A	1.406 (5)	C8B—C13B	1.401 (5)
C9A—C10A	1.369 (6)	C8B—C9B	1.403 (5)
C9A—H9A	0.9300	C9B—C10B	1.368 (6)
C10A—C11A	1.392 (5)	C9B—H9B	0.9300
C10A—H10A	0.9301	C10B—C11B	1.386 (5)
C11A—C12A	1.392 (5)	C10B—H10B	0.9300
C12A—C13A	1.383 (5)	C11B—C12B	1.393 (5)
C12A—H12A	0.9299	C12B—C13B	1.386 (5)
C13A—H13A	0.9299	C12B—H12B	0.9302
C14A—H14A	0.9600	C13B—H13B	0.9301
C14A—H14B	0.9600	C14B—H14D	0.9600
C14A—H14C	0.9600	C14B—H14E	0.9600
C15A—H15A	0.9600	C14B—H14F	0.9600
C15A—H15B	0.9600	C15B—H15D	0.9600
C15A—H15C	0.9600	C15B—H15E	0.9600
C16A—C17A	1.390 (4)	C15B—H15F	0.9600
C16A—C21A	1.395 (4)	C16B—C21B	1.386 (5)
C17A—C18A	1.375 (5)	C16B—C17B	1.389 (5)
C17A—H17A	0.9299	C17B—C18B	1.389 (5)
C18A—C19A	1.378 (5)	C17B—H17B	0.9302
C18A—H18A	0.9301	C18B—C19B	1.374 (5)
C19A—C20A	1.391 (5)	C18B—H18B	0.9300
C20A—C21A	1.383 (5)	C19B—C20B	1.395 (5)
C20A—H20A	0.9300	C20B—C21B	1.389 (5)
C21A—H21A	0.9301	C20B—H20B	0.9301
S1B—O4BB	1.38 (3)	C21B—H21B	0.9298
S1B—O3BB	1.39 (3)
O3A—S1A—O4A	112.6 (2)	O2BA—S1B—O4BA	114.6 (6)
O3A—S1A—O2A	112.83 (19)	O3BA—S1B—O4BA	114.1 (5)
O4A—S1A—O2A	113.1 (2)	O4BB—S1B—O2BB	111.7 (16)
O3A—S1A—C16A	105.92 (15)	O3BB—S1B—O2BB	105.5 (14)
O4A—S1A—C16A	105.44 (16)	O3BA—S1B—O2BB	94 (2)
O2A—S1A—C16A	106.16 (16)	O4BA—S1B—O2BB	128.3 (12)
C11A—O1A—C14A	117.8 (3)	O4BB—S1B—C16B	110.4 (13)
C1A—N1A—C5A	120.8 (4)	O3BB—S1B—C16B	111.3 (14)
C1A—N1A—C15A	118.2 (3)	O2BA—S1B—C16B	103.8 (4)
C5A—N1A—C15A	121.0 (3)	O3BA—S1B—C16B	103.3 (5)
C2A—C1A—N1A	121.1 (4)	O4BA—S1B—C16B	104.0 (5)
C2A—C1A—H1A	119.5	O2BB—S1B—C16B	111.0 (14)
N1A—C1A—H1A	119.5	C11B—O1B—C14B	118.8 (3)
C1A—C2A—C3A	119.6 (4)	C1B—N1B—C5B	121.5 (4)
C1A—C2A—H2A	120.2	C1B—N1B—C15B	117.2 (3)
C3A—C2A—H2A	120.2	C5B—N1B—C15B	121.2 (3)
C4A—C3A—C2A	119.2 (4)	N1B—C1B—C2B	121.4 (4)
C4A—C3A—H3A	120.4	N1B—C1B—H1B	119.3
C2A—C3A—H3A	120.4	C2B—C1B—H1B	119.3
C3A—C4A—C5A	121.6 (4)	C1B—C2B—C3B	119.2 (5)
C3A—C4A—H4A	119.2	C1B—C2B—H2B	120.4
C5A—C4A—H4A	119.2	C3B—C2B—H2B	120.4
N1A—C5A—C4A	117.7 (4)	C4B—C3B—C2B	119.4 (5)
N1A—C5A—C6A	116.9 (4)	C4B—C3B—H3B	120.3
C4A—C5A—C6A	125.3 (4)	C2B—C3B—H3B	120.3
C7A—C6A—C5A	122.9 (4)	C3B—C4B—C5B	120.8 (4)
C7A—C6A—H6A	118.6	C3B—C4B—H4B	119.6
C5A—C6A—H6A	118.6	C5B—C4B—H4B	119.6
C6A—C7A—C8A	125.4 (4)	N1B—C5B—C4B	117.7 (4)
C6A—C7A—H7A	117.3	N1B—C5B—C6B	117.9 (4)
C8A—C7A—H7A	117.3	C4B—C5B—C6B	124.4 (4)
C13A—C8A—C9A	116.9 (4)	C7B—C6B—C5B	123.5 (4)
C13A—C8A—C7A	120.1 (3)	C7B—C6B—H6B	118.3
C9A—C8A—C7A	122.9 (3)	C5B—C6B—H6B	118.3
C10A—C9A—C8A	121.4 (3)	C6B—C7B—C8B	126.0 (4)
C10A—C9A—H9A	119.3	C6B—C7B—H7B	117.0
C8A—C9A—H9A	119.3	C8B—C7B—H7B	117.0
C9A—C10A—C11A	120.2 (3)	C13B—C8B—C9B	117.3 (4)
C9A—C10A—H10A	119.9	C13B—C8B—C7B	119.5 (4)
C11A—C10A—H10A	119.9	C9B—C8B—C7B	123.2 (4)
O1A—C11A—C10A	115.8 (3)	C10B—C9B—C8B	121.4 (4)
O1A—C11A—C12A	124.0 (3)	C10B—C9B—H9B	119.3
C10A—C11A—C12A	120.2 (3)	C8B—C9B—H9B	119.3
C13A—C12A—C11A	118.6 (3)	C9B—C10B—C11B	120.3 (4)
C13A—C12A—H12A	120.7	C9B—C10B—H10B	119.8
C11A—C12A—H12A	120.6	C11B—C10B—H10B	119.8
C12A—C13A—C8A	122.6 (3)	O1B—C11B—C10B	115.6 (3)
C12A—C13A—H13A	118.7	O1B—C11B—C12B	124.2 (3)
C8A—C13A—H13A	118.7	C10B—C11B—C12B	120.2 (4)
O1A—C14A—H14A	109.5	C13B—C12B—C11B	118.8 (3)
O1A—C14A—H14B	109.5	C13B—C12B—H12B	120.6
H14A—C14A—H14B	109.5	C11B—C12B—H12B	120.6
O1A—C14A—H14C	109.5	C12B—C13B—C8B	121.9 (3)
H14A—C14A—H14C	109.5	C12B—C13B—H13B	119.1
H14B—C14A—H14C	109.5	C8B—C13B—H13B	119.0
N1A—C15A—H15A	109.5	O1B—C14B—H14D	109.5
N1A—C15A—H15B	109.5	O1B—C14B—H14E	109.5
H15A—C15A—H15B	109.5	H14D—C14B—H14E	109.5
N1A—C15A—H15C	109.5	O1B—C14B—H14F	109.5
H15A—C15A—H15C	109.5	H14D—C14B—H14F	109.5
H15B—C15A—H15C	109.5	H14E—C14B—H14F	109.5
C17A—C16A—C21A	119.8 (3)	N1B—C15B—H15D	109.5
C17A—C16A—S1A	120.6 (3)	N1B—C15B—H15E	109.5
C21A—C16A—S1A	119.6 (2)	H15D—C15B—H15E	109.5
C18A—C17A—C16A	120.7 (3)	N1B—C15B—H15F	109.5
C18A—C17A—H17A	119.8	H15D—C15B—H15F	109.5
C16A—C17A—H17A	119.5	H15E—C15B—H15F	109.5
C17A—C18A—C19A	118.4 (3)	C21B—C16B—C17B	119.9 (3)
C17A—C18A—H18A	120.7	C21B—C16B—S1B	118.8 (2)
C19A—C18A—H18A	120.9	C17B—C16B—S1B	121.3 (3)
C18A—C19A—C20A	122.7 (3)	C16B—C17B—C18B	120.0 (3)
C18A—C19A—Cl1A	119.4 (3)	C16B—C17B—H17B	120.0
C20A—C19A—Cl1A	117.9 (3)	C18B—C17B—H17B	120.0
C21A—C20A—C19A	118.0 (3)	C19B—C18B—C17B	119.4 (3)
C21A—C20A—H20A	121.1	C19B—C18B—H18B	120.3
C19A—C20A—H20A	120.9	C17B—C18B—H18B	120.2
C20A—C21A—C16A	120.4 (3)	C18B—C19B—C20B	121.6 (3)
C20A—C21A—H21A	119.9	C18B—C19B—Cl1B	119.6 (3)
C16A—C21A—H21A	119.8	C20B—C19B—Cl1B	118.8 (3)
O4BB—S1B—O3BB	106.7 (18)	C21B—C20B—C19B	118.3 (3)
O4BB—S1B—O2BA	97 (2)	C21B—C20B—H20B	120.8
O3BB—S1B—O2BA	126.0 (17)	C19B—C20B—H20B	120.8
O4BB—S1B—O3BA	125.5 (18)	C16B—C21B—C20B	120.7 (3)
O2BA—S1B—O3BA	114.9 (8)	C16B—C21B—H21B	119.7
O3BB—S1B—O4BA	95 (3)	C20B—C21B—H21B	119.6
C5A—N1A—C1A—C2A	−0.5 (6)	C1B—C2B—C3B—C4B	0.5 (6)
C15A—N1A—C1A—C2A	−179.7 (4)	C2B—C3B—C4B—C5B	0.7 (6)
N1A—C1A—C2A—C3A	−0.5 (6)	C1B—N1B—C5B—C4B	1.2 (5)
C1A—C2A—C3A—C4A	0.2 (6)	C15B—N1B—C5B—C4B	−179.5 (3)
C2A—C3A—C4A—C5A	1.2 (6)	C1B—N1B—C5B—C6B	−177.6 (3)
C1A—N1A—C5A—C4A	1.8 (5)	C15B—N1B—C5B—C6B	1.7 (5)
C15A—N1A—C5A—C4A	−179.0 (3)	C3B—C4B—C5B—N1B	−1.5 (6)
C1A—N1A—C5A—C6A	−175.8 (3)	C3B—C4B—C5B—C6B	177.3 (4)
C15A—N1A—C5A—C6A	3.3 (5)	N1B—C5B—C6B—C7B	168.8 (4)
C3A—C4A—C5A—N1A	−2.1 (6)	C4B—C5B—C6B—C7B	−10.0 (6)
C3A—C4A—C5A—C6A	175.3 (4)	C5B—C6B—C7B—C8B	179.3 (4)
N1A—C5A—C6A—C7A	167.7 (4)	C6B—C7B—C8B—C13B	−168.4 (4)
C4A—C5A—C6A—C7A	−9.8 (6)	C6B—C7B—C8B—C9B	12.3 (6)
C5A—C6A—C7A—C8A	179.7 (4)	C13B—C8B—C9B—C10B	0.1 (5)
C6A—C7A—C8A—C13A	−169.0 (4)	C7B—C8B—C9B—C10B	179.4 (4)
C6A—C7A—C8A—C9A	13.3 (6)	C8B—C9B—C10B—C11B	0.1 (6)
C13A—C8A—C9A—C10A	−0.5 (5)	C14B—O1B—C11B—C10B	174.1 (3)
C7A—C8A—C9A—C10A	177.3 (4)	C14B—O1B—C11B—C12B	−6.6 (5)
C8A—C9A—C10A—C11A	0.5 (6)	C9B—C10B—C11B—O1B	179.3 (3)
C14A—O1A—C11A—C10A	170.1 (3)	C9B—C10B—C11B—C12B	−0.1 (5)
C14A—O1A—C11A—C12A	−10.1 (5)	O1B—C11B—C12B—C13B	−179.3 (3)
C9A—C10A—C11A—O1A	179.8 (3)	C10B—C11B—C12B—C13B	0.0 (5)
C9A—C10A—C11A—C12A	0.0 (5)	C11B—C12B—C13B—C8B	0.2 (5)
O1A—C11A—C12A—C13A	179.7 (3)	C9B—C8B—C13B—C12B	−0.2 (5)
C10A—C11A—C12A—C13A	−0.5 (5)	C7B—C8B—C13B—C12B	−179.6 (3)
C11A—C12A—C13A—C8A	0.6 (5)	O4BB—S1B—C16B—C21B	79 (3)
C9A—C8A—C13A—C12A	−0.1 (5)	O3BB—S1B—C16B—C21B	−40 (3)
C7A—C8A—C13A—C12A	−177.9 (3)	O2BA—S1B—C16B—C21B	−178.1 (8)
O3A—S1A—C16A—C17A	−150.6 (3)	O3BA—S1B—C16B—C21B	−57.8 (5)
O4A—S1A—C16A—C17A	89.8 (3)	O4BA—S1B—C16B—C21B	61.7 (5)
O2A—S1A—C16A—C17A	−30.4 (3)	O2BB—S1B—C16B—C21B	−157 (3)
O3A—S1A—C16A—C21A	29.4 (3)	O4BB—S1B—C16B—C17B	−103 (3)
O4A—S1A—C16A—C21A	−90.1 (3)	O3BB—S1B—C16B—C17B	139 (3)
O2A—S1A—C16A—C21A	149.6 (3)	O2BA—S1B—C16B—C17B	0.5 (8)
C21A—C16A—C17A—C18A	−1.7 (5)	O3BA—S1B—C16B—C17B	120.7 (5)
S1A—C16A—C17A—C18A	178.3 (2)	O4BA—S1B—C16B—C17B	−119.8 (5)
C16A—C17A—C18A—C19A	−0.3 (5)	O2BB—S1B—C16B—C17B	22 (3)
C17A—C18A—C19A—C20A	2.1 (5)	C21B—C16B—C17B—C18B	1.3 (5)
C17A—C18A—C19A—Cl1A	−176.5 (2)	S1B—C16B—C17B—C18B	−177.2 (2)
C18A—C19A—C20A—C21A	−1.7 (5)	C16B—C17B—C18B—C19B	1.1 (5)
Cl1A—C19A—C20A—C21A	176.9 (2)	C17B—C18B—C19B—C20B	−3.0 (5)
C19A—C20A—C21A—C16A	−0.4 (4)	C17B—C18B—C19B—Cl1B	176.1 (2)
C17A—C16A—C21A—C20A	2.1 (5)	C18B—C19B—C20B—C21B	2.5 (5)
S1A—C16A—C21A—C20A	−177.9 (2)	Cl1B—C19B—C20B—C21B	−176.7 (2)
C5B—N1B—C1B—C2B	−0.1 (6)	C17B—C16B—C21B—C20B	−1.9 (5)
C15B—N1B—C1B—C2B	−179.4 (4)	S1B—C16B—C21B—C20B	176.7 (2)
N1B—C1B—C2B—C3B	−0.7 (6)	C19B—C20B—C21B—C16B	0.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O2A^i	0.93	2.34	3.203 (5)	155
C3A—H3A···O3A^ii	0.93	2.56	3.420 (6)	154
C6A—H6A···O4BA^iii	0.93	2.59	3.343 (12)	139
C7B—H7B···O4A^ii	0.93	2.44	3.244 (6)	145
C15A—H15B···O2A^i	0.96	2.47	3.368 (5)	155
C15A—H15C···O4BA^iii	0.96	2.29	3.194 (13)	156
C15B—H15E···O4A	0.96	2.54	3.456 (6)	159
C17B—H17B···O2BA	0.93	2.48	2.850 (15)	104
C20A—H20A···O2BA^iv	0.93	2.33	3.207 (17)	158
C20B—H20B···O2A^v	0.93	2.53	3.282 (6)	138
C9A—H9A···Cg5^iii	0.93	3.36	3.857 (4)	116
C9B—H9B···Cg4	0.93	3.15	3.706 (4)	120
C10A—H10A···Cg5^iii	0.93	2.97	3.652 (4)	131
C10B—H10B···Cg1^iv	0.93	3.32	3.628 (6)	102
C10B—H10B···Cg4	0.93	3.14	3.695 (4)	121
C12A—H12A···Cg4^vi	0.93	2.68	3.475 (4)	144
C12B—H12B···Cg5	0.93	2.69	3.470 (4)	142
C15A—H15A···Cg3^vii	0.96	2.67	3.449 (5)	138
C15B—H15F···Cg2^iv	0.96	2.78	3.532 (5)	136

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