Benzyl­tributyl­ammonium 4-hydroxynaphthalene-1-sulfonate

The title compound, C₁₉H₃₄N⁺·C₁₀H₇O₄S⁻, is a charge-control agent used in electrophotography. The anions form chains along the b axis through O—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
Some non-H atoms missing
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.162
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          3
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C7

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H2A    ..  H5AA    ..       1.94 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H5BA   ..  H13B    ..       1.96 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H9B    ..  H6BA    ..       1.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C7     ..  C4B     ..       3.18 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C29 H41 N1 O4 S1
            Atom count from the _atom_site data:  C29 H41.16 N1 O4 S1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C29 H41 N O4 S
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        116.00    116.00    0.00
           H        164.00    164.64   -0.64
           N          4.00      4.00    0.00
           O         16.00     16.00    0.00
           S          4.00      4.00    0.00

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

Benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate

Crystal data

C19H34N^+·C10H7O4S^−	F(000) = 1080.00
Mr = 499.70	Dx = 1.191 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 24226 reflections
a = 14.3810 (11) Å	θ = 3.0–68.3°
b = 9.8124 (7) Å	µ = 1.29 mm^−1
c = 19.7757 (15) Å	T = 296 K
β = 92.560 (5)°	Block, colorless
V = 2787.8 (4) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3490 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.0 pixels mm^-1	Rint = 0.036
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→17
Tmin = 0.745, Tmax = 0.772	k = −10→11
24226 measured reflections	l = −23→23
4902 independent reflections

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0921P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max < 0.001
wR(F^2) = 0.162	Δρmax = 0.45 e Å^−3
S = 1.19	Δρmin = −0.24 e Å^−3
4902 reflections	Extinction correction: SHELXL97
347 parameters	Extinction coefficient: 0.0013 (2)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.12147 (4)	0.20730 (6)	0.12699 (3)	0.0592 (2)
O1	0.06337 (11)	0.20811 (16)	0.18621 (8)	0.0683 (4)
O2	0.08159 (11)	0.29017 (16)	0.07230 (8)	0.0684 (4)
O3	0.14619 (12)	0.07074 (16)	0.10626 (8)	0.0732 (4)
O4	0.45491 (12)	0.5297 (2)	0.21416 (10)	0.0843 (5)
H4	0.4436	0.5779	0.2467	0.101*
N1	0.49198 (14)	0.1596 (2)	0.37120 (9)	0.0732 (5)
C1	0.53476 (17)	0.2977 (2)	0.35867 (13)	0.0702 (6)
H1A	0.5914	0.2838	0.3347	0.084*
H1B	0.4921	0.3488	0.3289	0.084*
C2	0.5581 (2)	0.3839 (3)	0.42023 (15)	0.0863 (8)
H2A	0.5010	0.4101	0.4411	0.104*
H2B	0.5951	0.3308	0.4528	0.104*
C3	0.6111 (2)	0.5101 (4)	0.4021 (2)	0.1275 (13)
H3A	0.5826	0.5466	0.3605	0.153*	0.74
H3B	0.6028	0.5772	0.4373	0.153*	0.74
H3C	0.6462	0.4838	0.3633	0.153*	0.26
H3D	0.5640	0.5734	0.3848	0.153*	0.26
C4A	0.7055 (3)	0.4972 (4)	0.3931 (2)	0.1061 (18)*	0.742 (7)
H4A1	0.7307	0.5843	0.3816	0.159*	0.742 (7)
H4A2	0.7155	0.4335	0.3573	0.159*	0.742 (7)
H4A3	0.7358	0.4650	0.4343	0.159*	0.742 (7)
C4B	0.6689 (9)	0.5845 (12)	0.4397 (5)	0.095 (4)*	0.258 (7)
H4B1	0.6908	0.6593	0.4134	0.142*	0.258 (7)
H4B2	0.7208	0.5296	0.4552	0.142*	0.258 (7)
H4B3	0.6374	0.6190	0.4779	0.142*	0.258 (7)
C5A	0.4047 (3)	0.2144 (6)	0.4087 (3)	0.079 (2)*	0.460 (6)
H5AA	0.4258	0.2486	0.4527	0.094*	0.460 (6)
H5AB	0.3784	0.2906	0.3831	0.094*	0.460 (6)
C5B	0.4144 (3)	0.1398 (7)	0.4218 (2)	0.0725 (17)*	0.540 (6)
H5BA	0.3974	0.0442	0.4234	0.087*	0.540 (6)
H5BB	0.4372	0.1668	0.4667	0.087*	0.540 (6)
C6A	0.3275 (3)	0.1099 (5)	0.4186 (3)	0.0764 (19)*	0.460 (6)
H6AA	0.3023	0.0761	0.3755	0.092*	0.460 (6)
H6AB	0.3502	0.0336	0.4458	0.092*	0.460 (6)
C6B	0.3291 (3)	0.2240 (5)	0.4012 (2)	0.0743 (16)*	0.540 (6)
H6BA	0.3055	0.1988	0.3562	0.089*	0.540 (6)
H6BB	0.3440	0.3204	0.4014	0.089*	0.540 (6)
C7	0.2552 (2)	0.1912 (4)	0.4553 (2)	0.1292 (13)
H7A	0.2223	0.1228	0.4803	0.155*	0.540 (6)
H7B	0.2916	0.2422	0.4891	0.155*	0.540 (6)
H7C	0.2349	0.0971	0.4524	0.155*	0.540 (6)
H7D	0.2781	0.2121	0.5010	0.155*	0.540 (6)
C8	0.1815 (2)	0.2875 (4)	0.4324 (2)	0.1437 (16)
H8A	0.1299	0.2802	0.4613	0.216*
H8B	0.1612	0.2662	0.3867	0.216*
H8C	0.2056	0.3788	0.4343	0.216*
C9	0.4574 (2)	0.0961 (3)	0.30449 (13)	0.0900 (8)
H9A	0.4502	−0.0010	0.3118	0.108*
H9B	0.3960	0.1326	0.2933	0.108*
C10	0.51588 (18)	0.1150 (3)	0.24359 (12)	0.0774 (7)
H10A	0.5803	0.0932	0.2556	0.093*
H10B	0.5130	0.2094	0.2290	0.093*
C11	0.4804 (2)	0.0229 (3)	0.18628 (14)	0.1026 (10)
H11A	0.4767	−0.0695	0.2034	0.123*
H11B	0.4179	0.0512	0.1723	0.123*
C12	0.5367 (3)	0.0221 (5)	0.1273 (2)	0.1549 (17)
H12A	0.5101	−0.0396	0.0941	0.232*
H12B	0.5988	−0.0069	0.1402	0.232*
H12C	0.5387	0.1122	0.1085	0.232*
C13	0.5605 (2)	0.0640 (3)	0.40984 (14)	0.0885 (9)
H13A	0.5815	0.1091	0.4514	0.106*
H13B	0.5268	−0.0171	0.4224	0.106*
C14	0.6446 (2)	0.0203 (2)	0.37334 (14)	0.0811 (7)
C15	0.6465 (3)	−0.1035 (3)	0.34006 (17)	0.1043 (10)
H15A	0.5946	−0.1602	0.3399	0.125*
C16	0.7245 (4)	−0.1438 (4)	0.3070 (2)	0.1278 (14)
H16A	0.7244	−0.2263	0.2839	0.153*
C17	0.8020 (3)	−0.0625 (4)	0.3082 (2)	0.1214 (12)
H17A	0.8542	−0.0903	0.2858	0.146*
C18	0.8032 (2)	0.0593 (4)	0.3420 (2)	0.1191 (12)
H18A	0.8559	0.1144	0.3426	0.143*
C19	0.7253 (2)	0.0992 (3)	0.37508 (17)	0.0942 (9)
H19A	0.7267	0.1807	0.3991	0.113*
C20	0.37932 (16)	0.4523 (2)	0.19705 (12)	0.0627 (6)
C21	0.30718 (16)	0.4331 (2)	0.23837 (12)	0.0644 (6)
H21A	0.3086	0.4730	0.2811	0.077*
C22	0.23052 (16)	0.3528 (2)	0.21645 (11)	0.0603 (5)
H22A	0.1815	0.3409	0.2450	0.072*
C23	0.22618 (15)	0.2919 (2)	0.15434 (11)	0.0553 (5)
C24	0.30233 (16)	0.3049 (2)	0.11095 (11)	0.0587 (5)
C25	0.30554 (18)	0.2400 (2)	0.04718 (12)	0.0728 (7)
H25A	0.2561	0.1854	0.0319	0.087*
C26	0.3798 (2)	0.2563 (3)	0.00804 (14)	0.0885 (8)
H26A	0.3805	0.2122	−0.0336	0.106*
C27	0.4549 (2)	0.3378 (3)	0.02884 (15)	0.0922 (8)
H27A	0.5051	0.3482	0.0012	0.111*
C28	0.45463 (18)	0.4026 (3)	0.09027 (14)	0.0819 (7)
H28A	0.5047	0.4575	0.1040	0.098*
C29	0.37953 (15)	0.3870 (2)	0.13276 (11)	0.0603 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0646 (3)	0.0516 (4)	0.0604 (3)	−0.0011 (2)	−0.0075 (2)	0.0007 (2)
O1	0.0662 (9)	0.0689 (11)	0.0699 (10)	−0.0040 (8)	0.0023 (7)	0.0031 (8)
O2	0.0752 (10)	0.0614 (11)	0.0669 (9)	0.0016 (7)	−0.0151 (8)	0.0044 (7)
O3	0.0867 (11)	0.0517 (11)	0.0806 (10)	−0.0001 (8)	−0.0037 (8)	−0.0085 (8)
O4	0.0676 (10)	0.0950 (15)	0.0900 (13)	−0.0152 (9)	0.0014 (8)	−0.0283 (10)
N1	0.0689 (12)	0.0943 (16)	0.0564 (11)	−0.0212 (11)	0.0016 (9)	0.0009 (10)
C1	0.0589 (13)	0.0755 (18)	0.0755 (15)	0.0043 (12)	−0.0034 (11)	0.0106 (13)
C2	0.0804 (17)	0.079 (2)	0.098 (2)	0.0043 (15)	−0.0082 (15)	−0.0071 (16)
C3	0.124 (2)	0.097 (2)	0.157 (3)	−0.008 (2)	−0.046 (2)	0.015 (2)
C7	0.080 (2)	0.155 (3)	0.154 (3)	0.010 (2)	0.024 (2)	−0.025 (2)
C8	0.096 (2)	0.134 (3)	0.205 (4)	0.004 (2)	0.040 (2)	0.025 (3)
C9	0.0878 (18)	0.114 (2)	0.0679 (16)	−0.0290 (17)	−0.0028 (13)	−0.0050 (15)
C10	0.0827 (17)	0.088 (2)	0.0610 (14)	0.0026 (14)	−0.0039 (12)	0.0061 (13)
C11	0.109 (2)	0.124 (2)	0.0742 (18)	0.005 (2)	−0.0033 (17)	−0.0138 (18)
C12	0.155 (3)	0.210 (4)	0.101 (2)	0.010 (3)	0.020 (2)	−0.032 (2)
C13	0.123 (2)	0.074 (2)	0.0671 (16)	−0.0305 (17)	−0.0120 (16)	0.0127 (13)
C14	0.107 (2)	0.0600 (18)	0.0741 (16)	−0.0023 (15)	−0.0244 (15)	0.0085 (13)
C15	0.157 (3)	0.067 (2)	0.086 (2)	−0.007 (2)	−0.030 (2)	−0.0014 (16)
C16	0.186 (4)	0.093 (3)	0.101 (2)	0.036 (3)	−0.033 (2)	−0.019 (2)
C17	0.126 (3)	0.107 (3)	0.128 (3)	0.039 (2)	−0.025 (2)	−0.013 (2)
C18	0.085 (2)	0.106 (3)	0.163 (3)	0.028 (2)	−0.031 (2)	−0.013 (2)
C19	0.090 (2)	0.0690 (19)	0.120 (2)	0.0116 (16)	−0.0375 (17)	−0.0069 (16)
C20	0.0585 (13)	0.0626 (16)	0.0661 (14)	−0.0018 (11)	−0.0061 (11)	−0.0039 (11)
C21	0.0679 (14)	0.0703 (17)	0.0543 (12)	0.0004 (12)	−0.0066 (10)	−0.0105 (11)
C22	0.0632 (13)	0.0637 (15)	0.0538 (12)	−0.0012 (11)	0.0015 (10)	−0.0023 (10)
C23	0.0591 (12)	0.0505 (14)	0.0556 (12)	0.0009 (10)	−0.0046 (9)	−0.0006 (10)
C24	0.0647 (13)	0.0552 (14)	0.0555 (12)	0.0073 (10)	−0.0034 (10)	−0.0024 (10)
C25	0.0752 (16)	0.0832 (18)	0.0596 (14)	0.0021 (13)	0.0002 (12)	−0.0135 (12)
C26	0.092 (2)	0.107 (2)	0.0675 (16)	0.0078 (17)	0.0077 (15)	−0.0222 (15)
C27	0.0837 (19)	0.113 (2)	0.0817 (19)	−0.0018 (17)	0.0249 (15)	−0.0107 (17)
C28	0.0689 (16)	0.096 (2)	0.0814 (17)	−0.0077 (14)	0.0081 (13)	−0.0095 (15)
C29	0.0596 (13)	0.0627 (15)	0.0586 (12)	0.0037 (10)	0.0004 (10)	−0.0019 (10)

Geometric parameters (Å, º)

S1—O1	1.4687 (17)	C7—H7D	0.970
S1—O2	1.4507 (16)	C7—C8	1.475 (5)
S1—O3	1.4502 (16)	C8—H8A	0.960
S1—C23	1.782 (2)	C8—H8B	0.960
O4—H4	0.820	C8—H8C	0.960
O4—C20	1.357 (2)	C9—H9A	0.970
N1—C1	1.513 (3)	C9—H9B	0.970
N1—C5A	1.580 (6)	C9—C10	1.511 (3)
N1—C5B	1.544 (5)	C10—H10A	0.970
N1—C9	1.522 (3)	C10—H10B	0.970
N1—C13	1.538 (3)	C10—C11	1.520 (4)
C1—H1A	0.970	C11—H11A	0.970
C1—H1B	0.970	C11—H11B	0.970
C1—C2	1.508 (3)	C11—C12	1.450 (5)
C2—H2A	0.970	C12—H12A	0.960
C2—H2B	0.970	C12—H12B	0.960
C2—C3	1.506 (5)	C12—H12C	0.960
C3—H3A	0.970	C13—H13A	0.970
C3—H3B	0.970	C13—H13B	0.970
C3—H3C	0.970	C13—C14	1.499 (4)
C3—H3D	0.970	C14—C15	1.382 (4)
C3—C4A	1.382 (6)	C14—C19	1.395 (4)
C3—C4B	1.312 (12)	C15—H15A	0.930
H3A—H3D	0.618	C15—C16	1.381 (6)
H3B—C4B	0.952	C16—H16A	0.930
H3C—C4A	1.023	C16—C17	1.370 (7)
C4A—H4A1	0.960	C17—H17A	0.930
C4A—H4A2	0.960	C17—C18	1.369 (5)
C4A—H4A3	0.960	C18—H18A	0.930
C4A—C4B	1.378 (12)	C18—C19	1.380 (4)
C4B—H4B1	0.960	C19—H19A	0.930
C4B—H4B2	0.960	C20—C21	1.362 (3)
C4B—H4B3	0.960	C20—C29	1.424 (3)
C5A—H5AA	0.970	C21—H21A	0.930
C5A—H5AB	0.970	C21—C22	1.408 (3)
C5A—C6A	1.529 (7)	C22—H22A	0.930
C5B—H5BA	0.970	C22—C23	1.365 (3)
C5B—H5BB	0.970	C23—C24	1.427 (3)
C5B—C6B	1.520 (6)	C24—C25	1.415 (3)
C6A—H6AA	0.970	C24—C29	1.423 (3)
C6A—H6AB	0.970	C25—H25A	0.930
C6A—C7	1.521 (6)	C25—C26	1.356 (3)
C6B—H6BA	0.970	C26—H26A	0.930
C6B—H6BB	0.970	C26—C27	1.391 (4)
C6B—C7	1.574 (5)	C27—H27A	0.930
C7—H7A	0.970	C27—C28	1.371 (4)
C7—H7B	0.970	C28—H28A	0.930
C7—H7C	0.970	C28—C29	1.406 (3)
O1···O4^i	2.657 (2)	H5BA···O2^i	2.512
O1···H4^i	1.848	H5BB···H4B3^iv	2.622
O1···H3D^i	2.617	H5BB···H13B^viii	2.672
O1···H15A^ii	2.645	H6AB···O2^i	2.613
O2···H2B^iii	2.659	H6AB···H13A^viii	2.623
O2···H5BA^ii	2.512	H6BB···O3^ii	2.466
O2···H6AB^ii	2.613	H6BB···H4B3^iv	2.463
O2···H13A^iii	2.587	H7B···C4B^iv	2.264
O2···H13B^ii	2.456	H7B···H4B1^iv	2.161
O3···H6BB^i	2.466	H7B···H4B2^iv	2.505
O3···H21A^i	2.486	H7B···H4B3^iv	1.807
O4···O1^ii	2.657 (2)	H7D···C4B^iv	2.421
H4···O1^ii	1.848	H7D···H4B1^iv	2.142
H2A···H4B3^iv	2.625	H7D···H4B2^iv	2.679
H2B···O2^v	2.659	H7D···H4B3^iv	2.087
H3D···O1^ii	2.617	H8A···H27A^ix	2.357
H4A1···H12B^vi	2.663	H8C···H4B2^iv	2.548
H4A1···H16A^vii	2.678	H9A···H22A^i	2.659
H4A3···H25A^v	2.437	H11A···H22A^i	2.682
C4B···H7B^iv	2.264	H12A···H26A^x	2.636
C4B···H7D^iv	2.421	H12B···H4A1^xi	2.663
H4B1···H7B^iv	2.161	H13A···O2^v	2.587
H4B1···H7D^iv	2.142	H13A···H6AB^viii	2.623
H4B1···H15A^vii	2.643	H13B···O2^i	2.456
H4B2···H7B^iv	2.505	H13B···H5BB^viii	2.672
H4B2···H7D^iv	2.679	H15A···O1^i	2.645
H4B2···H8C^iv	2.548	H15A···H4B1^xii	2.643
H4B2···H25A^v	2.634	H16A···H4A1^xii	2.678
H4B3···H2A^iv	2.625	H21A···O3^ii	2.486
H4B3···H5AA^iv	2.123	H22A···H9A^ii	2.659
H4B3···H5BB^iv	2.622	H22A···H11A^ii	2.682
H4B3···H6BB^iv	2.463	H25A···H4A3^iii	2.437
H4B3···H7B^iv	1.807	H25A···H4B2^iii	2.634
H4B3···H7D^iv	2.087	H26A···H12A^x	2.636
H5AA···H4B3^iv	2.123	H27A···H8A^xiii	2.357
O1—S1—O2	111.80 (9)	H7B—C7—C8	103.9
O1—S1—O3	112.69 (9)	H7C—C7—H7D	110.1
O1—S1—C23	104.98 (9)	H7C—C7—C8	112.5
O2—S1—O3	113.64 (9)	H7D—C7—C8	111.1
O2—S1—C23	105.42 (9)	C7—C8—H8A	109.5
O3—S1—C23	107.55 (10)	C7—C8—H8B	109.5
H4—O4—C20	109.5	C7—C8—H8C	109.5
C1—N1—C5A	96.3 (2)	H8A—C8—H8B	109.5
C1—N1—C5B	122.0 (3)	H8A—C8—H8C	109.5
C1—N1—C9	110.12 (19)	H8B—C8—H8C	109.5
C1—N1—C13	111.79 (19)	N1—C9—H9A	107.8
C5A—N1—C9	108.1 (2)	N1—C9—H9B	107.8
C5A—N1—C13	118.6 (2)	N1—C9—C10	118.0 (2)
C5B—N1—C9	107.0 (2)	H9A—C9—H9B	107.1
C5B—N1—C13	93.8 (2)	H9A—C9—C10	107.8
C9—N1—C13	111.0 (2)	H9B—C9—C10	107.8
N1—C1—H1A	108.1	C9—C10—H10A	109.7
N1—C1—H1B	108.1	C9—C10—H10B	109.7
N1—C1—C2	116.6 (2)	C9—C10—C11	110.0 (2)
H1A—C1—H1B	107.3	H10A—C10—H10B	108.2
H1A—C1—C2	108.1	H10A—C10—C11	109.7
H1B—C1—C2	108.1	H10B—C10—C11	109.7
C1—C2—H2A	109.3	C10—C11—H11A	108.5
C1—C2—H2B	109.3	C10—C11—H11B	108.5
C1—C2—C3	111.4 (2)	C10—C11—C12	115.0 (3)
H2A—C2—H2B	108.0	H11A—C11—H11B	107.5
H2A—C2—C3	109.3	H11A—C11—C12	108.5
H2B—C2—C3	109.3	H11B—C11—C12	108.5
C2—C3—H3A	107.9	C11—C12—H12A	109.5
C2—C3—H3B	107.9	C11—C12—H12B	109.5
C2—C3—H3C	104.9	C11—C12—H12C	109.5
C2—C3—H3D	104.9	H12A—C12—H12B	109.5
C2—C3—C4A	117.8 (3)	H12A—C12—H12C	109.5
C2—C3—C4B	129.5 (5)	H12B—C12—H12C	109.5
H3A—C3—H3B	107.2	N1—C13—H13A	108.1
H3A—C3—C4A	107.8	N1—C13—H13B	108.1
H3B—C3—C4A	107.9	N1—C13—C14	116.6 (2)
H3C—C3—H3D	105.8	H13A—C13—H13B	107.3
H3C—C3—C4B	104.9	H13A—C13—C14	108.1
H3D—C3—C4B	104.9	H13B—C13—C14	108.1
C3—C4A—H4A1	109.5	C13—C14—C15	121.0 (3)
C3—C4A—H4A2	109.5	C13—C14—C19	121.2 (2)
C3—C4A—H4A3	109.5	C15—C14—C19	117.8 (3)
H4A1—C4A—H4A2	109.5	C14—C15—H15A	119.7
H4A1—C4A—H4A3	109.5	C14—C15—C16	120.7 (3)
H4A2—C4A—H4A3	109.5	H15A—C15—C16	119.7
C3—C4B—H4B1	109.5	C15—C16—H16A	119.9
C3—C4B—H4B2	109.5	C15—C16—C17	120.2 (3)
C3—C4B—H4B3	109.5	H16A—C16—C17	119.9
H3B—C4B—H4B1	112.4	C16—C17—H17A	119.7
H3B—C4B—H4B2	137.2	C16—C17—C18	120.6 (4)
H4B1—C4B—H4B2	109.5	H17A—C17—C18	119.7
H4B1—C4B—H4B3	109.5	C17—C18—H18A	120.5
H4B2—C4B—H4B3	109.5	C17—C18—C19	119.1 (3)
N1—C5A—H5AA	108.4	H18A—C18—C19	120.5
N1—C5A—H5AB	108.4	C14—C19—C18	121.6 (3)
N1—C5A—C6A	115.4 (4)	C14—C19—H19A	119.2
H5AA—C5A—H5AB	107.5	C18—C19—H19A	119.2
H5AA—C5A—C6A	108.4	O4—C20—C21	123.5 (2)
H5AB—C5A—C6A	108.4	O4—C20—C29	116.2 (2)
N1—C5B—H5BA	109.5	C21—C20—C29	120.3 (2)
N1—C5B—H5BB	109.5	C20—C21—H21A	120.0
N1—C5B—C6B	110.9 (4)	C20—C21—C22	120.0 (2)
C5A—C5B—H5BA	150.4	H21A—C21—C22	120.0
C5A—C5B—H5BB	95.4	C21—C22—H22A	119.1
H5BA—C5B—H5BB	108.0	C21—C22—C23	121.7 (2)
H5BA—C5B—C6B	109.5	H22A—C22—C23	119.1
H5BB—C5B—C6B	109.5	S1—C23—C22	118.76 (17)
C5A—C6A—H6AA	111.2	S1—C23—C24	121.33 (16)
C5A—C6A—H6AB	111.2	C22—C23—C24	119.8 (2)
C5A—C6A—C7	103.0 (4)	C23—C24—C25	123.5 (2)
H6AA—C6A—H6AB	109.1	C23—C24—C29	118.55 (19)
H6AA—C6A—C7	111.2	C25—C24—C29	118.0 (2)
H6AB—C6A—C7	111.2	C24—C25—H25A	119.6
C5B—C6B—H6BA	110.6	C24—C25—C26	120.9 (2)
C5B—C6B—H6BB	110.6	H25A—C25—C26	119.6
C5B—C6B—C7	105.5 (3)	C25—C26—H26A	119.3
H6BA—C6B—H6BB	108.8	C25—C26—C27	121.3 (2)
H6BA—C6B—C7	110.6	H26A—C26—C27	119.3
H6BB—C6B—C7	110.6	C26—C27—H27A	120.2
C6A—C7—H7A	103.9	C26—C27—C28	119.7 (2)
C6A—C7—H7B	103.9	H27A—C27—C28	120.2
C6A—C7—C8	133.4 (3)	C27—C28—H28A	119.6
C6B—C7—H7C	111.4	C27—C28—C29	120.8 (2)
C6B—C7—H7D	112.3	H28A—C28—C29	119.6
C6B—C7—C8	99.1 (3)	C20—C29—C24	119.5 (2)
H7A—C7—H7B	105.4	C20—C29—C28	121.1 (2)
H7A—C7—C8	103.9	C24—C29—C28	119.4 (2)
O1—S1—C23—C22	−7.5 (2)	N1—C13—C14—C19	86.7 (3)
O1—S1—C23—C24	176.82 (17)	C13—C14—C15—C16	−179.4 (3)
O2—S1—C23—C22	110.66 (18)	C13—C14—C19—C18	179.6 (3)
O2—S1—C23—C24	−64.97 (19)	C15—C14—C19—C18	3.2 (4)
O3—S1—C23—C22	−127.78 (18)	C19—C14—C15—C16	−3.0 (4)
O3—S1—C23—C24	56.6 (2)	C14—C15—C16—C17	1.5 (5)
C1—N1—C5A—C6A	167.5 (4)	C15—C16—C17—C18	0.0 (5)
C5A—N1—C1—C2	58.4 (3)	C16—C17—C18—C19	0.1 (4)
C1—N1—C5B—C6B	60.5 (4)	C17—C18—C19—C14	−1.8 (5)
C5B—N1—C1—C2	43.7 (3)	O4—C20—C21—C22	179.1 (2)
C1—N1—C9—C10	38.8 (3)	O4—C20—C29—C24	−179.5 (2)
C9—N1—C1—C2	170.3 (2)	O4—C20—C29—C28	0.3 (3)
C1—N1—C13—C14	−66.5 (2)	C21—C20—C29—C24	2.1 (3)
C13—N1—C1—C2	−65.9 (2)	C21—C20—C29—C28	−178.2 (2)
C5A—N1—C9—C10	142.8 (3)	C29—C20—C21—C22	−2.6 (3)
C9—N1—C5A—C6A	53.9 (5)	C20—C21—C22—C23	0.4 (3)
C5A—N1—C13—C14	−177.1 (3)	C21—C22—C23—S1	−173.35 (17)
C13—N1—C5A—C6A	−73.5 (5)	C21—C22—C23—C24	2.3 (3)
C5B—N1—C9—C10	173.4 (3)	S1—C23—C24—C25	−7.5 (3)
C9—N1—C5B—C6B	−67.5 (4)	S1—C23—C24—C29	172.78 (16)
C5B—N1—C13—C14	166.7 (3)	C22—C23—C24—C25	176.9 (2)
C13—N1—C5B—C6B	179.2 (3)	C22—C23—C24—C29	−2.8 (3)
C9—N1—C13—C14	56.9 (3)	C23—C24—C25—C26	179.9 (2)
C13—N1—C9—C10	−85.6 (2)	C23—C24—C29—C20	0.6 (3)
N1—C1—C2—C3	172.7 (2)	C23—C24—C29—C28	−179.1 (2)
C1—C2—C3—C4A	−80.2 (4)	C25—C24—C29—C20	−179.1 (2)
C1—C2—C3—C4B	−154.9 (8)	C25—C24—C29—C28	1.1 (3)
N1—C5A—C6A—C7	179.9 (2)	C29—C24—C25—C26	−0.4 (3)
N1—C5B—C6B—C7	178.4 (3)	C24—C25—C26—C27	−0.4 (4)
C5B—C6B—C7—C8	175.3 (3)	C25—C26—C27—C28	0.4 (4)
N1—C9—C10—C11	169.1 (2)	C26—C27—C28—C29	0.4 (4)
C9—C10—C11—C12	−174.2 (3)	C27—C28—C29—C20	179.1 (2)
N1—C13—C14—C15	−97.0 (3)	C27—C28—C29—C24	−1.2 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1^ii	0.82	1.85	2.657 (2)	169

Symmetry code: (ii) −x+1/2, y+1/2, −z+1/2.