(3,5-Di­methyl­adamantan-1-yl)ammonium methane­sulfonate (memanti­nium mesylate): synthesis, structure and solid-state properties

The title salt crystallizes with three independent ionic pairs in the asymmetric unit. In the crystal, (3,5-di­methyl­adamantan-1-yl)ammonium cations and methane­sulfonate anions associate via N—H...O hydrogen bonds into layers that extend parallel to (001) and comprise large supra­molecular hydrogen-bonded rings.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.133
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S3 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          9 Report
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C5          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C15         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C17         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C27         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C29         (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          9 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         73 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku, 2018); cell refinement: CrysAlis PRO (Rigaku, 2018); data reduction: CrysAlis PRO (Rigaku, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

(3,5-Dimethyladamantan-1-yl)ammonium methanesulfonate

Crystal data

C12H22N^+·CH3O3S^−	Z = 6
Mr = 275.40	F(000) = 900
Triclinic, P1	Dx = 1.210 Mg m^−3
a = 11.7761 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.8731 (2) Å	Cell parameters from 30823 reflections
c = 18.2788 (3) Å	θ = 5.1–72.7°
α = 92.501 (2)°	µ = 1.92 mm^−1
β = 94.696 (2)°	T = 295 K
γ = 116.609 (2)°	Prism, colorless
V = 2268.09 (8) Å^3	0.32 × 0.21 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer	8992 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	8048 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 16.1285 pixels mm^-1	θmax = 72.9°, θmin = 4.2°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2018)	k = −14→14
Tmin = 0.200, Tmax = 1.000	l = −22→22
76762 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0822P)^2 + 0.429P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
8992 reflections	Δρmax = 0.86 e Å^−3
523 parameters	Δρmin = −0.53 e Å^−3
9 restraints

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
S1	0.63651 (4)	0.78463 (4)	0.39086 (2)	0.04527 (12)
S2	0.67423 (4)	0.34333 (4)	0.38657 (2)	0.04606 (12)
S3	0.12114 (4)	0.83219 (4)	0.39052 (2)	0.04759 (12)
O2	0.51832 (13)	0.79458 (13)	0.39206 (8)	0.0608 (3)
O6	0.66922 (13)	0.21916 (12)	0.38512 (8)	0.0615 (3)
O3	0.63630 (13)	0.68285 (13)	0.43196 (8)	0.0637 (4)
O9	0.22683 (12)	0.95327 (12)	0.38131 (8)	0.0597 (3)
N2	0.46247 (14)	−0.01597 (13)	0.33925 (7)	0.0433 (3)
H2A	0.4793 (18)	−0.0755 (16)	0.3563 (11)	0.052*
H2B	0.3914 (16)	−0.0237 (19)	0.3549 (11)	0.052*
H2C	0.5300 (16)	0.0593 (15)	0.3524 (11)	0.052*
N3	0.84089 (14)	0.66545 (13)	0.50755 (7)	0.0443 (3)
H3A	0.7713 (16)	0.6768 (19)	0.4943 (11)	0.053*
H3B	0.8237 (19)	0.5892 (15)	0.4864 (11)	0.053*
H3C	0.9054 (17)	0.7263 (17)	0.4886 (11)	0.053*
O5	0.78864 (13)	0.43837 (13)	0.42985 (9)	0.0681 (4)
O8	0.03123 (14)	0.84536 (14)	0.43564 (9)	0.0701 (4)
O1	0.66929 (16)	0.77755 (15)	0.31635 (8)	0.0689 (4)
N1	0.79465 (15)	0.63192 (15)	0.27752 (8)	0.0492 (3)
H1A	0.8792 (15)	0.6704 (19)	0.2924 (11)	0.059*
H1B	0.7552 (19)	0.6784 (19)	0.2896 (11)	0.059*
H1C	0.7541 (19)	0.5562 (16)	0.2945 (11)	0.059*
O4	0.65613 (18)	0.37874 (16)	0.31366 (8)	0.0799 (4)
O7	0.06024 (15)	0.75862 (18)	0.32090 (8)	0.0807 (5)
C1	0.78006 (15)	0.61136 (14)	0.19499 (8)	0.0403 (3)
C13	0.44439 (15)	−0.03377 (14)	0.25673 (8)	0.0410 (3)
C21	0.57125 (16)	−0.00684 (16)	0.22910 (9)	0.0466 (3)
H21A	0.602030	−0.063954	0.248806	0.056*
H21B	0.633874	0.079104	0.245897	0.056*
C2	0.85215 (15)	0.73767 (14)	0.16319 (9)	0.0437 (3)
H2D	0.941858	0.775209	0.182302	0.052*
H2E	0.818326	0.795085	0.177964	0.052*
C25	0.86750 (14)	0.67267 (14)	0.58989 (8)	0.0388 (3)
C8	0.63814 (16)	0.55422 (17)	0.16706 (9)	0.0495 (4)
H8A	0.603732	0.611128	0.181834	0.059*
H8B	0.591700	0.474521	0.187850	0.059*
C14	0.39642 (17)	0.05787 (16)	0.22769 (9)	0.0465 (4)
H14A	0.458103	0.144183	0.244420	0.056*
H14B	0.316197	0.041308	0.246425	0.056*
C33	0.74579 (15)	0.58585 (15)	0.62134 (9)	0.0465 (4)
H33A	0.716038	0.499680	0.600214	0.056*
H33B	0.679657	0.611394	0.608577	0.056*
C3	0.83830 (16)	0.71802 (15)	0.07895 (9)	0.0461 (3)
C9	0.83407 (18)	0.52124 (16)	0.17324 (9)	0.0494 (4)
H9A	0.789149	0.441714	0.194516	0.059*
H9B	0.923813	0.557457	0.192103	0.059*
C29	0.77116 (18)	0.59194 (16)	0.70548 (10)	0.0515 (4)
C17	0.55484 (18)	−0.02435 (18)	0.14428 (9)	0.0518 (4)
C20	0.34628 (19)	−0.17022 (16)	0.23234 (10)	0.0550 (4)
H20A	0.265548	−0.187900	0.250751	0.066*
H20B	0.376024	−0.228155	0.251938	0.066*
C7	0.62339 (17)	0.53292 (18)	0.08302 (10)	0.0570 (4)
H7	0.532571	0.496120	0.064282	0.068*
C10	0.69578 (17)	0.65902 (18)	0.05044 (10)	0.0551 (4)
H10A	0.661208	0.716286	0.064169	0.066*
H10B	0.685028	0.645408	−0.002913	0.066*
C27	0.94396 (19)	0.81789 (16)	0.70574 (10)	0.0550 (4)
C28	0.82115 (19)	0.72963 (17)	0.73701 (10)	0.0547 (4)
H28A	0.756156	0.757187	0.725515	0.066*
H28B	0.837695	0.734841	0.790224	0.066*
C32	0.97039 (18)	0.63053 (19)	0.60735 (10)	0.0533 (4)
H32A	1.047882	0.685745	0.587058	0.064*
H32B	0.941860	0.544971	0.585529	0.064*
C26	0.91308 (17)	0.80841 (14)	0.62144 (9)	0.0480 (4)
H26A	0.847120	0.834588	0.609658	0.058*
H26B	0.988817	0.864055	0.599813	0.058*
C15	0.37718 (19)	0.04088 (19)	0.14298 (10)	0.0541 (4)
C4	0.89072 (19)	0.62571 (18)	0.05718 (10)	0.0547 (4)
H4A	0.980834	0.662137	0.075195	0.066*
H4B	0.882463	0.612470	0.003875	0.066*
C16	0.50501 (19)	0.06612 (19)	0.11542 (10)	0.0560 (4)
H16A	0.494476	0.056705	0.061962	0.067*
H16B	0.567400	0.152538	0.131348	0.067*
C5	0.8188 (2)	0.49778 (17)	0.08899 (10)	0.0581 (4)
C31	0.99688 (19)	0.6358 (2)	0.69101 (11)	0.0613 (5)
H31	1.062627	0.608260	0.703034	0.074*
C34	1.04425 (19)	0.7718 (2)	0.72352 (11)	0.0667 (5)
H34A	1.122481	0.826226	0.703591	0.080*
H34B	1.063191	0.776712	0.776554	0.080*
C18	0.4547 (2)	−0.16083 (19)	0.11936 (11)	0.0642 (5)
H18A	0.442643	−0.173304	0.065954	0.077*
H18B	0.484759	−0.219250	0.137810	0.077*
C30	0.8754 (2)	0.55030 (19)	0.72313 (11)	0.0622 (5)
H30A	0.893369	0.553496	0.776130	0.075*
H30B	0.845513	0.463685	0.702762	0.075*
C22	0.2800 (2)	−0.0963 (2)	0.11844 (11)	0.0669 (5)
H22A	0.265956	−0.108476	0.065038	0.080*
H22B	0.199032	−0.114068	0.136608	0.080*
C11	0.9113 (2)	0.84445 (19)	0.04648 (12)	0.0637 (5)
H11A	0.906209	0.830026	−0.006045	0.096*
H11B	0.999280	0.882959	0.067192	0.096*
H11C	0.874229	0.899532	0.057953	0.096*
C6	0.6764 (2)	0.44274 (18)	0.06038 (11)	0.0675 (6)
H6A	0.665622	0.428149	0.007073	0.081*
H6B	0.629446	0.362181	0.080179	0.081*
C19	0.3283 (2)	−0.18780 (18)	0.14795 (11)	0.0624 (5)
H19	0.265373	−0.274972	0.131457	0.075*
C37	0.7589 (2)	0.9253 (2)	0.43596 (13)	0.0725 (6)
H37A	0.839530	0.923855	0.434650	0.109*
H37B	0.743534	0.933165	0.486261	0.109*
H37C	0.760564	0.996040	0.411638	0.109*
C24	0.6820 (2)	0.0025 (3)	0.11616 (13)	0.0750 (6)
H24A	0.716007	−0.048908	0.139055	0.112*
H24B	0.741106	0.090204	0.128023	0.112*
H24C	0.669158	−0.016810	0.063679	0.112*
C39	0.1879 (3)	0.7482 (2)	0.43919 (13)	0.0772 (6)
H39A	0.121442	0.666667	0.446964	0.116*
H39B	0.230009	0.794210	0.485935	0.116*
H39C	0.248720	0.737812	0.411344	0.116*
C23	0.3304 (3)	0.1337 (3)	0.11357 (13)	0.0826 (7)
H23A	0.390720	0.218550	0.131858	0.124*
H23B	0.248716	0.114611	0.129763	0.124*
H23C	0.322531	0.126083	0.060676	0.124*
C36	0.6483 (2)	0.5065 (2)	0.73711 (14)	0.0810 (7)
H36A	0.614309	0.422261	0.713577	0.122*
H36B	0.586811	0.538270	0.728493	0.122*
H36C	0.666388	0.505295	0.789161	0.122*
C38	0.5456 (2)	0.3353 (3)	0.43141 (15)	0.0786 (6)
H38A	0.541871	0.414355	0.430089	0.118*
H38B	0.556891	0.318705	0.481714	0.118*
H38C	0.467537	0.268600	0.407036	0.118*
C35	0.9899 (3)	0.9543 (2)	0.73805 (14)	0.0888 (8)
H35A	0.924801	0.980266	0.725943	0.133*
H35B	1.066459	1.008865	0.717829	0.133*
H35C	1.007226	0.959284	0.790653	0.133*
C12	0.8726 (4)	0.4071 (3)	0.06721 (16)	0.0966 (9)
H12A	0.860777	0.390739	0.014533	0.145*
H12B	0.828734	0.329128	0.089069	0.145*
H12C	0.962179	0.444489	0.084328	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0487 (2)	0.0458 (2)	0.0460 (2)	0.02573 (18)	0.00387 (16)	0.00512 (15)
S2	0.0469 (2)	0.0452 (2)	0.0465 (2)	0.02134 (17)	0.00555 (16)	0.00208 (15)
S3	0.0452 (2)	0.0508 (2)	0.0449 (2)	0.01982 (18)	0.00683 (16)	0.00448 (16)
O2	0.0593 (8)	0.0671 (8)	0.0715 (8)	0.0403 (7)	0.0124 (6)	0.0197 (6)
O6	0.0610 (8)	0.0462 (6)	0.0745 (9)	0.0241 (6)	−0.0017 (6)	−0.0025 (6)
O3	0.0582 (8)	0.0571 (7)	0.0800 (9)	0.0301 (6)	−0.0012 (7)	0.0199 (6)
O9	0.0518 (7)	0.0555 (7)	0.0734 (8)	0.0235 (6)	0.0180 (6)	0.0126 (6)
N2	0.0448 (7)	0.0447 (7)	0.0426 (7)	0.0218 (6)	0.0052 (6)	0.0063 (5)
N3	0.0466 (8)	0.0460 (7)	0.0408 (7)	0.0222 (6)	0.0014 (6)	0.0012 (5)
O5	0.0549 (8)	0.0566 (7)	0.0888 (10)	0.0262 (6)	−0.0052 (7)	−0.0202 (7)
O8	0.0662 (9)	0.0684 (8)	0.0819 (10)	0.0310 (7)	0.0342 (7)	0.0145 (7)
O1	0.0861 (10)	0.0835 (9)	0.0517 (7)	0.0504 (8)	0.0150 (7)	0.0031 (6)
N1	0.0524 (8)	0.0561 (8)	0.0377 (7)	0.0238 (7)	0.0040 (6)	0.0008 (6)
O4	0.1053 (12)	0.0754 (10)	0.0541 (8)	0.0353 (9)	0.0109 (8)	0.0192 (7)
O7	0.0631 (9)	0.1011 (12)	0.0585 (8)	0.0245 (8)	−0.0072 (7)	−0.0159 (8)
C1	0.0414 (8)	0.0436 (7)	0.0347 (7)	0.0188 (6)	0.0020 (6)	0.0012 (5)
C13	0.0452 (8)	0.0406 (7)	0.0389 (7)	0.0213 (6)	0.0030 (6)	0.0042 (6)
C21	0.0471 (9)	0.0523 (9)	0.0459 (8)	0.0277 (7)	0.0041 (7)	0.0049 (6)
C2	0.0418 (8)	0.0392 (7)	0.0460 (8)	0.0157 (6)	0.0002 (6)	0.0008 (6)
C25	0.0394 (8)	0.0398 (7)	0.0388 (7)	0.0199 (6)	0.0019 (6)	0.0019 (5)
C8	0.0396 (8)	0.0561 (9)	0.0469 (9)	0.0163 (7)	0.0059 (7)	0.0045 (7)
C14	0.0502 (9)	0.0506 (8)	0.0477 (8)	0.0306 (7)	0.0058 (7)	0.0076 (7)
C33	0.0417 (8)	0.0416 (8)	0.0499 (9)	0.0141 (7)	0.0029 (7)	0.0008 (6)
C3	0.0453 (8)	0.0458 (8)	0.0436 (8)	0.0175 (7)	0.0030 (6)	0.0079 (6)
C9	0.0583 (10)	0.0490 (8)	0.0482 (9)	0.0293 (8)	0.0122 (7)	0.0101 (7)
C29	0.0529 (10)	0.0469 (8)	0.0500 (9)	0.0174 (7)	0.0119 (7)	0.0068 (7)
C17	0.0551 (10)	0.0605 (10)	0.0454 (8)	0.0310 (8)	0.0075 (7)	0.0030 (7)
C20	0.0577 (10)	0.0423 (8)	0.0570 (10)	0.0159 (8)	0.0051 (8)	0.0049 (7)
C7	0.0425 (9)	0.0619 (10)	0.0463 (9)	0.0079 (8)	−0.0052 (7)	0.0014 (7)
C10	0.0501 (10)	0.0640 (10)	0.0459 (9)	0.0222 (8)	−0.0034 (7)	0.0089 (7)
C27	0.0631 (11)	0.0425 (8)	0.0474 (9)	0.0149 (8)	0.0012 (8)	−0.0042 (7)
C28	0.0646 (11)	0.0566 (10)	0.0460 (9)	0.0300 (9)	0.0108 (8)	−0.0003 (7)
C32	0.0534 (10)	0.0683 (11)	0.0518 (9)	0.0396 (9)	0.0055 (7)	0.0049 (8)
C26	0.0532 (9)	0.0369 (7)	0.0486 (9)	0.0162 (7)	0.0029 (7)	0.0024 (6)
C15	0.0604 (10)	0.0673 (11)	0.0453 (9)	0.0385 (9)	0.0020 (7)	0.0099 (7)
C4	0.0619 (11)	0.0598 (10)	0.0468 (9)	0.0292 (9)	0.0168 (8)	0.0087 (7)
C16	0.0650 (11)	0.0644 (10)	0.0447 (8)	0.0335 (9)	0.0100 (8)	0.0131 (7)
C5	0.0807 (13)	0.0510 (9)	0.0505 (9)	0.0346 (9)	0.0211 (9)	0.0042 (7)
C31	0.0606 (11)	0.0860 (13)	0.0547 (10)	0.0495 (11)	−0.0007 (8)	0.0110 (9)
C34	0.0477 (10)	0.0842 (14)	0.0510 (10)	0.0175 (10)	−0.0082 (8)	0.0000 (9)
C18	0.0839 (14)	0.0612 (11)	0.0528 (10)	0.0394 (11)	0.0032 (9)	−0.0076 (8)
C30	0.0843 (14)	0.0586 (10)	0.0519 (10)	0.0391 (10)	0.0062 (9)	0.0132 (8)
C22	0.0564 (11)	0.0861 (14)	0.0511 (10)	0.0291 (10)	−0.0084 (8)	−0.0019 (9)
C11	0.0627 (11)	0.0570 (10)	0.0664 (11)	0.0210 (9)	0.0078 (9)	0.0226 (9)
C6	0.0829 (14)	0.0473 (9)	0.0471 (9)	0.0088 (9)	0.0043 (9)	−0.0066 (7)
C19	0.0633 (11)	0.0510 (10)	0.0567 (10)	0.0146 (9)	−0.0034 (9)	−0.0094 (8)
C37	0.0709 (13)	0.0549 (11)	0.0742 (13)	0.0149 (10)	0.0018 (11)	−0.0047 (9)
C24	0.0710 (14)	0.1042 (17)	0.0612 (12)	0.0486 (13)	0.0164 (10)	0.0057 (11)
C39	0.1087 (19)	0.0742 (13)	0.0702 (13)	0.0590 (14)	0.0121 (12)	0.0177 (11)
C23	0.1070 (19)	0.1152 (19)	0.0631 (13)	0.0822 (17)	0.0089 (12)	0.0256 (12)
C36	0.0736 (15)	0.0771 (14)	0.0745 (14)	0.0141 (12)	0.0283 (12)	0.0176 (11)
C38	0.0623 (13)	0.0978 (17)	0.0868 (16)	0.0438 (13)	0.0230 (11)	0.0076 (13)
C35	0.122 (2)	0.0487 (11)	0.0681 (13)	0.0174 (12)	0.0026 (13)	−0.0133 (9)
C12	0.157 (3)	0.0811 (16)	0.0877 (17)	0.0780 (18)	0.0545 (18)	0.0141 (13)

Geometric parameters (Å, º)

S1—O3	1.4497 (13)	C10—H10A	0.9700
S1—O2	1.4503 (13)	C10—H10B	0.9700
S1—O1	1.4548 (14)	C27—C34	1.527 (3)
S1—C37	1.754 (2)	C27—C35	1.531 (3)
S2—O4	1.4427 (15)	C27—C28	1.532 (3)
S2—O6	1.4478 (13)	C27—C26	1.541 (2)
S2—O5	1.4491 (14)	C28—H28A	0.9700
S2—C38	1.748 (2)	C28—H28B	0.9700
S3—O7	1.4453 (15)	C32—C31	1.528 (2)
S3—O9	1.4480 (14)	C32—H32A	0.9700
S3—O8	1.4511 (14)	C32—H32B	0.9700
S3—C39	1.751 (2)	C26—H26A	0.9700
N2—C13	1.4983 (19)	C26—H26B	0.9700
N2—H2A	0.878 (15)	C15—C16	1.531 (3)
N2—H2B	0.873 (15)	C15—C22	1.532 (3)
N2—H2C	0.896 (15)	C15—C23	1.534 (3)
N3—C25	1.5026 (19)	C4—C5	1.539 (3)
N3—H3A	0.904 (15)	C4—H4A	0.9700
N3—H3B	0.896 (15)	C4—H4B	0.9700
N3—H3C	0.890 (15)	C16—H16A	0.9700
N1—C1	1.5008 (19)	C16—H16B	0.9700
N1—H1A	0.901 (15)	C5—C12	1.528 (3)
N1—H1B	0.897 (16)	C5—C6	1.535 (3)
N1—H1C	0.893 (15)	C31—C30	1.520 (3)
C1—C9	1.524 (2)	C31—C34	1.526 (3)
C1—C2	1.525 (2)	C31—H31	0.9800
C1—C8	1.526 (2)	C34—H34A	0.9700
C13—C21	1.516 (2)	C34—H34B	0.9700
C13—C20	1.528 (2)	C18—C19	1.519 (3)
C13—C14	1.529 (2)	C18—H18A	0.9700
C21—C17	1.540 (2)	C18—H18B	0.9700
C21—H21A	0.9700	C30—H30A	0.9700
C21—H21B	0.9700	C30—H30B	0.9700
C2—C3	1.532 (2)	C22—C19	1.533 (3)
C2—H2D	0.9700	C22—H22A	0.9700
C2—H2E	0.9700	C22—H22B	0.9700
C25—C33	1.520 (2)	C11—H11A	0.9600
C25—C26	1.520 (2)	C11—H11B	0.9600
C25—C32	1.521 (2)	C11—H11C	0.9600
C8—C7	1.529 (2)	C6—H6A	0.9700
C8—H8A	0.9700	C6—H6B	0.9700
C8—H8B	0.9700	C19—H19	0.9800
C14—C15	1.538 (2)	C37—H37A	0.9600
C14—H14A	0.9700	C37—H37B	0.9600
C14—H14B	0.9700	C37—H37C	0.9600
C33—C29	1.535 (2)	C24—H24A	0.9600
C33—H33A	0.9700	C24—H24B	0.9600
C33—H33B	0.9700	C24—H24C	0.9600
C3—C4	1.533 (3)	C39—H39A	0.9600
C3—C11	1.533 (2)	C39—H39B	0.9600
C3—C10	1.533 (2)	C39—H39C	0.9600
C9—C5	1.534 (2)	C23—H23A	0.9600
C9—H9A	0.9700	C23—H23B	0.9600
C9—H9B	0.9700	C23—H23C	0.9600
C29—C36	1.527 (3)	C36—H36A	0.9600
C29—C30	1.532 (3)	C36—H36B	0.9600
C29—C28	1.533 (2)	C36—H36C	0.9600
C17—C24	1.524 (3)	C38—H38A	0.9600
C17—C16	1.530 (2)	C38—H38B	0.9600
C17—C18	1.536 (3)	C38—H38C	0.9600
C20—C19	1.532 (3)	C35—H35A	0.9600
C20—H20A	0.9700	C35—H35B	0.9600
C20—H20B	0.9700	C35—H35C	0.9600
C7—C6	1.520 (3)	C12—H12A	0.9600
C7—C10	1.530 (3)	C12—H12B	0.9600
C7—H7	0.9800	C12—H12C	0.9600
O3—S1—O2	112.16 (8)	C27—C28—H28B	109.3
O3—S1—O1	112.49 (9)	C29—C28—H28B	109.3
O2—S1—O1	112.24 (9)	H28A—C28—H28B	107.9
O3—S1—C37	106.48 (10)	C25—C32—C31	108.64 (14)
O2—S1—C37	106.90 (11)	C25—C32—H32A	110.0
O1—S1—C37	106.03 (11)	C31—C32—H32A	110.0
O4—S2—O6	112.33 (9)	C25—C32—H32B	110.0
O4—S2—O5	112.53 (10)	C31—C32—H32B	110.0
O6—S2—O5	111.99 (8)	H32A—C32—H32B	108.3
O4—S2—C38	106.23 (12)	C25—C26—C27	109.43 (13)
O6—S2—C38	107.04 (11)	C25—C26—H26A	109.8
O5—S2—C38	106.18 (11)	C27—C26—H26A	109.8
O7—S3—O9	112.24 (10)	C25—C26—H26B	109.8
O7—S3—O8	112.80 (10)	C27—C26—H26B	109.8
O9—S3—O8	111.98 (8)	H26A—C26—H26B	108.2
O7—S3—C39	106.65 (12)	C16—C15—C22	108.80 (16)
O9—S3—C39	105.98 (11)	C16—C15—C23	110.50 (17)
O8—S3—C39	106.65 (11)	C22—C15—C23	111.15 (18)
C13—N2—H2A	108.9 (13)	C16—C15—C14	108.38 (14)
C13—N2—H2B	108.9 (13)	C22—C15—C14	108.47 (15)
H2A—N2—H2B	108.3 (18)	C23—C15—C14	109.49 (16)
C13—N2—H2C	107.2 (13)	C3—C4—C5	111.38 (15)
H2A—N2—H2C	109.0 (18)	C3—C4—H4A	109.4
H2B—N2—H2C	114.4 (18)	C5—C4—H4A	109.4
C25—N3—H3A	111.5 (13)	C3—C4—H4B	109.4
C25—N3—H3B	111.5 (13)	C5—C4—H4B	109.4
H3A—N3—H3B	105.7 (18)	H4A—C4—H4B	108.0
C25—N3—H3C	111.2 (13)	C17—C16—C15	111.81 (15)
H3A—N3—H3C	105.8 (18)	C17—C16—H16A	109.3
H3B—N3—H3C	110.8 (19)	C15—C16—H16A	109.3
C1—N1—H1A	106.7 (14)	C17—C16—H16B	109.3
C1—N1—H1B	107.8 (14)	C15—C16—H16B	109.3
H1A—N1—H1B	113 (2)	H16A—C16—H16B	107.9
C1—N1—H1C	107.3 (14)	C12—C5—C9	109.66 (18)
H1A—N1—H1C	112.9 (19)	C12—C5—C6	110.9 (2)
H1B—N1—H1C	109 (2)	C9—C5—C6	108.75 (16)
N1—C1—C9	108.80 (13)	C12—C5—C4	110.77 (18)
N1—C1—C2	109.46 (12)	C9—C5—C4	108.30 (15)
C9—C1—C2	110.08 (13)	C6—C5—C4	108.38 (16)
N1—C1—C8	108.44 (13)	C30—C31—C34	109.47 (17)
C9—C1—C8	110.26 (14)	C30—C31—C32	110.15 (16)
C2—C1—C8	109.76 (13)	C34—C31—C32	108.73 (16)
N2—C13—C21	109.02 (12)	C30—C31—H31	109.5
N2—C13—C20	108.75 (13)	C34—C31—H31	109.5
C21—C13—C20	110.00 (14)	C32—C31—H31	109.5
N2—C13—C14	108.56 (12)	C31—C34—C27	110.87 (15)
C21—C13—C14	110.25 (13)	C31—C34—H34A	109.5
C20—C13—C14	110.23 (14)	C27—C34—H34A	109.5
C13—C21—C17	109.86 (13)	C31—C34—H34B	109.5
C13—C21—H21A	109.7	C27—C34—H34B	109.5
C17—C21—H21A	109.7	H34A—C34—H34B	108.1
C13—C21—H21B	109.7	C19—C18—C17	110.38 (15)
C17—C21—H21B	109.7	C19—C18—H18A	109.6
H21A—C21—H21B	108.2	C17—C18—H18A	109.6
C1—C2—C3	110.01 (12)	C19—C18—H18B	109.6
C1—C2—H2D	109.7	C17—C18—H18B	109.6
C3—C2—H2D	109.7	H18A—C18—H18B	108.1
C1—C2—H2E	109.7	C31—C30—C29	110.54 (15)
C3—C2—H2E	109.7	C31—C30—H30A	109.5
H2D—C2—H2E	108.2	C29—C30—H30A	109.5
N3—C25—C33	109.30 (12)	C31—C30—H30B	109.5
N3—C25—C26	108.86 (12)	C29—C30—H30B	109.5
C33—C25—C26	109.96 (13)	H30A—C30—H30B	108.1
N3—C25—C32	108.23 (13)	C15—C22—C19	110.50 (15)
C33—C25—C32	110.02 (13)	C15—C22—H22A	109.5
C26—C25—C32	110.44 (14)	C19—C22—H22A	109.5
C1—C8—C7	108.38 (14)	C15—C22—H22B	109.5
C1—C8—H8A	110.0	C19—C22—H22B	109.5
C7—C8—H8A	110.0	H22A—C22—H22B	108.1
C1—C8—H8B	110.0	C3—C11—H11A	109.5
C7—C8—H8B	110.0	C3—C11—H11B	109.5
H8A—C8—H8B	108.4	H11A—C11—H11B	109.5
C13—C14—C15	109.31 (13)	C3—C11—H11C	109.5
C13—C14—H14A	109.8	H11A—C11—H11C	109.5
C15—C14—H14A	109.8	H11B—C11—H11C	109.5
C13—C14—H14B	109.8	C7—C6—C5	110.54 (14)
C15—C14—H14B	109.8	C7—C6—H6A	109.5
H14A—C14—H14B	108.3	C5—C6—H6A	109.5
C25—C33—C29	110.04 (13)	C7—C6—H6B	109.5
C25—C33—H33A	109.7	C5—C6—H6B	109.5
C29—C33—H33A	109.7	H6A—C6—H6B	108.1
C25—C33—H33B	109.7	C18—C19—C20	109.84 (16)
C29—C33—H33B	109.7	C18—C19—C22	109.75 (18)
H33A—C33—H33B	108.2	C20—C19—C22	108.95 (17)
C2—C3—C4	108.56 (13)	C18—C19—H19	109.4
C2—C3—C11	110.40 (14)	C20—C19—H19	109.4
C4—C3—C11	110.30 (15)	C22—C19—H19	109.4
C2—C3—C10	108.42 (14)	S1—C37—H37A	109.5
C4—C3—C10	108.78 (15)	S1—C37—H37B	109.5
C11—C3—C10	110.32 (14)	H37A—C37—H37B	109.5
C1—C9—C5	109.68 (14)	S1—C37—H37C	109.5
C1—C9—H9A	109.7	H37A—C37—H37C	109.5
C5—C9—H9A	109.7	H37B—C37—H37C	109.5
C1—C9—H9B	109.7	C17—C24—H24A	109.5
C5—C9—H9B	109.7	C17—C24—H24B	109.5
H9A—C9—H9B	108.2	H24A—C24—H24B	109.5
C36—C29—C30	111.16 (18)	C17—C24—H24C	109.5
C36—C29—C28	110.63 (17)	H24A—C24—H24C	109.5
C30—C29—C28	108.68 (16)	H24B—C24—H24C	109.5
C36—C29—C33	109.98 (16)	S3—C39—H39A	109.5
C30—C29—C33	107.91 (15)	S3—C39—H39B	109.5
C28—C29—C33	108.40 (14)	H39A—C39—H39B	109.5
C24—C17—C16	110.87 (17)	S3—C39—H39C	109.5
C24—C17—C18	110.44 (17)	H39A—C39—H39C	109.5
C16—C17—C18	108.76 (15)	H39B—C39—H39C	109.5
C24—C17—C21	110.12 (15)	C15—C23—H23A	109.5
C16—C17—C21	108.09 (14)	C15—C23—H23B	109.5
C18—C17—C21	108.49 (15)	H23A—C23—H23B	109.5
C13—C20—C19	108.48 (14)	C15—C23—H23C	109.5
C13—C20—H20A	110.0	H23A—C23—H23C	109.5
C19—C20—H20A	110.0	H23B—C23—H23C	109.5
C13—C20—H20B	110.0	C29—C36—H36A	109.5
C19—C20—H20B	110.0	C29—C36—H36B	109.5
H20A—C20—H20B	108.4	H36A—C36—H36B	109.5
C6—C7—C8	109.66 (16)	C29—C36—H36C	109.5
C6—C7—C10	109.48 (17)	H36A—C36—H36C	109.5
C8—C7—C10	109.83 (15)	H36B—C36—H36C	109.5
C6—C7—H7	109.3	S2—C38—H38A	109.5
C8—C7—H7	109.3	S2—C38—H38B	109.5
C10—C7—H7	109.3	H38A—C38—H38B	109.5
C7—C10—C3	110.09 (14)	S2—C38—H38C	109.5
C7—C10—H10A	109.6	H38A—C38—H38C	109.5
C3—C10—H10A	109.6	H38B—C38—H38C	109.5
C7—C10—H10B	109.6	C27—C35—H35A	109.5
C3—C10—H10B	109.6	C27—C35—H35B	109.5
H10A—C10—H10B	108.2	H35A—C35—H35B	109.5
C34—C27—C35	111.57 (19)	C27—C35—H35C	109.5
C34—C27—C28	108.39 (16)	H35A—C35—H35C	109.5
C35—C27—C28	110.15 (18)	H35B—C35—H35C	109.5
C34—C27—C26	109.22 (16)	C5—C12—H12A	109.5
C35—C27—C26	109.83 (16)	C5—C12—H12B	109.5
C28—C27—C26	107.59 (15)	H12A—C12—H12B	109.5
C27—C28—C29	111.83 (14)	C5—C12—H12C	109.5
C27—C28—H28A	109.3	H12A—C12—H12C	109.5
C29—C28—H28A	109.3	H12B—C12—H12C	109.5
N2—C13—C21—C17	−179.89 (13)	C35—C27—C26—C25	−179.97 (18)
C20—C13—C21—C17	60.96 (17)	C28—C27—C26—C25	−60.08 (19)
C14—C13—C21—C17	−60.81 (17)	C13—C14—C15—C16	−58.79 (19)
N1—C1—C2—C3	179.87 (13)	C13—C14—C15—C22	59.17 (19)
C9—C1—C2—C3	60.33 (17)	C13—C14—C15—C23	−179.39 (18)
C8—C1—C2—C3	−61.22 (17)	C2—C3—C4—C5	59.02 (19)
N1—C1—C8—C7	−179.81 (14)	C11—C3—C4—C5	−179.90 (16)
C9—C1—C8—C7	−60.78 (18)	C10—C3—C4—C5	−58.78 (19)
C2—C1—C8—C7	60.66 (18)	C24—C17—C16—C15	180.00 (16)
N2—C13—C14—C15	−179.95 (14)	C18—C17—C16—C15	58.4 (2)
C21—C13—C14—C15	60.69 (18)	C21—C17—C16—C15	−59.2 (2)
C20—C13—C14—C15	−60.94 (18)	C22—C15—C16—C17	−58.15 (19)
N3—C25—C33—C29	179.97 (13)	C23—C15—C16—C17	179.57 (17)
C26—C25—C33—C29	−60.58 (17)	C14—C15—C16—C17	59.6 (2)
C32—C25—C33—C29	61.26 (17)	C1—C9—C5—C12	−179.83 (19)
C1—C2—C3—C4	−58.56 (18)	C1—C9—C5—C6	−58.40 (19)
C1—C2—C3—C11	−179.59 (14)	C1—C9—C5—C4	59.2 (2)
C1—C2—C3—C10	59.46 (17)	C3—C4—C5—C12	−179.67 (19)
N1—C1—C9—C5	179.41 (14)	C3—C4—C5—C9	−59.4 (2)
C2—C1—C9—C5	−60.65 (18)	C3—C4—C5—C6	58.44 (19)
C8—C1—C9—C5	60.60 (18)	C25—C32—C31—C30	59.1 (2)
C25—C33—C29—C36	178.98 (17)	C25—C32—C31—C34	−60.8 (2)
C25—C33—C29—C30	−59.61 (18)	C30—C31—C34—C27	−60.0 (2)
C25—C33—C29—C28	57.92 (18)	C32—C31—C34—C27	60.4 (2)
C13—C21—C17—C24	−179.97 (16)	C35—C27—C34—C31	179.94 (18)
C13—C21—C17—C16	58.77 (18)	C28—C27—C34—C31	58.5 (2)
C13—C21—C17—C18	−59.00 (18)	C26—C27—C34—C31	−58.5 (2)
N2—C13—C20—C19	−179.97 (15)	C24—C17—C18—C19	179.54 (17)
C21—C13—C20—C19	−60.65 (19)	C16—C17—C18—C19	−58.6 (2)
C14—C13—C20—C19	61.13 (19)	C21—C17—C18—C19	58.8 (2)
C1—C8—C7—C6	60.18 (19)	C34—C31—C30—C29	59.6 (2)
C1—C8—C7—C10	−60.2 (2)	C32—C31—C30—C29	−59.9 (2)
C6—C7—C10—C3	−60.18 (19)	C36—C29—C30—C31	179.75 (18)
C8—C7—C10—C3	60.3 (2)	C28—C29—C30—C31	−58.3 (2)
C2—C3—C10—C7	−59.00 (19)	C33—C29—C30—C31	59.08 (19)
C4—C3—C10—C7	58.89 (19)	C16—C15—C22—C19	57.9 (2)
C11—C3—C10—C7	180.00 (16)	C23—C15—C22—C19	179.75 (18)
C34—C27—C28—C29	−58.18 (19)	C14—C15—C22—C19	−59.8 (2)
C35—C27—C28—C29	179.51 (18)	C8—C7—C6—C5	−60.2 (2)
C26—C27—C28—C29	59.8 (2)	C10—C7—C6—C5	60.35 (19)
C36—C29—C28—C27	−179.52 (17)	C12—C5—C6—C7	179.38 (17)
C30—C29—C28—C27	58.2 (2)	C9—C5—C6—C7	58.7 (2)
C33—C29—C28—C27	−58.9 (2)	C4—C5—C6—C7	−58.82 (19)
N3—C25—C32—C31	−179.24 (15)	C17—C18—C19—C20	−60.1 (2)
C33—C25—C32—C31	−59.88 (19)	C17—C18—C19—C22	59.7 (2)
C26—C25—C32—C31	61.68 (19)	C13—C20—C19—C18	60.0 (2)
N3—C25—C26—C27	−178.60 (14)	C13—C20—C19—C22	−60.3 (2)
C33—C25—C26—C27	61.69 (18)	C15—C22—C19—C18	−59.5 (2)
C32—C25—C26—C27	−59.91 (18)	C15—C22—C19—C20	60.8 (2)
C34—C27—C26—C25	57.37 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7^i	0.90 (2)	1.92 (2)	2.819 (2)	177 (2)
N1—H1B···O1	0.90 (2)	1.94 (2)	2.833 (2)	179 (2)
N1—H1C···O4	0.89 (2)	1.96 (2)	2.844 (2)	170 (2)
N2—H2A···O2^ii	0.88 (2)	1.92 (2)	2.7991 (18)	179 (2)
N2—H2B···O9^ii	0.87 (2)	1.94 (2)	2.8090 (19)	175 (2)
N2—H2C···O6	0.90 (2)	1.90 (2)	2.7923 (19)	177 (2)
N3—H3A···O3	0.90 (2)	1.91 (2)	2.7717 (19)	159 (2)
N3—H3B···O5	0.90 (2)	1.89 (2)	2.7752 (19)	172 (2)
N3—H3C···O8^i	0.89 (2)	1.90 (2)	2.785 (2)	172 (2)
C39—H39B···O6^iii	0.96	2.59	3.423 (3)	145

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