Crystal structure and Hirshfeld surface analysis of (RS)-3-hy­droxy-2-{[(3aRS,6RS,7aRS)-2-(4-methyl­phenyl­sulfon­yl)-2,3,3a,6,7,7a-hexa­hydro-3a,6-ep­oxy-1H-isoindol-6-yl]meth­yl}isoindolin-1-one

The title compound crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, strong inter­molecular O—H...O hydrogen bonds and weak inter­molecular C—H...O contacts link the mol­ecules, forming a three-dimensional network. In addition, weak π–π stacking inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.147
• Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8       ..O3       .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A     ..O5'      .       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15C     ..O2       .       2.62 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.376 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         16 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT343_ALERT_2_G Unusual sp3      Angle Range in Main Residue for        C13 Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3              95.7 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3'             95.4 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C8'         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C10         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C10'        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C13         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C13'        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C16         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C16'        (Centro SPGR)          R Verify
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         95 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
  13 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(RS)-3-Hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one

Crystal data

C24H24N2O5S	Z = 4
Mr = 452.51	F(000) = 952
Triclinic, P1	Dx = 1.358 Mg m^−3
a = 11.8210 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8395 (8) Å	Cell parameters from 5394 reflections
c = 16.7336 (11) Å	θ = 2.3–27.2°
α = 77.949 (1)°	µ = 0.19 mm^−1
β = 79.555 (1)°	T = 120 K
γ = 77.511 (1)°	Prism, colourless
V = 2213.3 (3) Å^3	0.15 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	13532 independent reflections
Radiation source: sealed tube	8799 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 30.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −16→16
Tmin = 0.688, Tmax = 0.746	k = −16→16
29692 measured reflections	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0474P)^2 + 1.6525P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
13532 reflections	Δρmax = 0.41 e Å^−3
581 parameters	Δρmin = −0.44 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
S1	0.74652 (5)	0.55414 (5)	0.53950 (3)	0.02594 (13)
O1	0.32628 (13)	0.11057 (14)	0.96738 (9)	0.0263 (3)
O2	0.71088 (13)	0.03280 (14)	0.88152 (10)	0.0278 (3)
H2	0.705699	−0.016702	0.931497	0.042 (8)*
O3	0.57170 (13)	0.31030 (12)	0.74923 (9)	0.0212 (3)
O4	0.75506 (15)	0.67311 (14)	0.53936 (11)	0.0353 (4)
O5	0.73338 (14)	0.51910 (15)	0.46520 (10)	0.0317 (4)
N1	0.50789 (16)	0.12179 (15)	0.89107 (10)	0.0221 (4)
N2	0.63120 (16)	0.52671 (16)	0.60548 (11)	0.0240 (4)
C1	0.41649 (19)	0.06714 (19)	0.92534 (12)	0.0216 (4)
C2	0.44704 (19)	−0.05190 (19)	0.90475 (13)	0.0235 (4)
C3	0.3823 (2)	−0.1414 (2)	0.92483 (14)	0.0280 (5)
H3	0.305319	−0.130549	0.954375	0.034*
C4	0.4354 (2)	−0.2480 (2)	0.89974 (15)	0.0334 (6)
H4	0.393844	−0.311270	0.912327	0.040*
C5	0.5482 (2)	−0.2629 (2)	0.85654 (15)	0.0339 (6)
H5	0.582760	−0.336705	0.840882	0.041*
C6	0.6117 (2)	−0.1720 (2)	0.83572 (15)	0.0310 (5)
H6	0.688286	−0.182161	0.805520	0.037*
C7	0.5589 (2)	−0.06640 (19)	0.86068 (13)	0.0242 (4)
C8	0.60631 (19)	0.04558 (19)	0.84880 (13)	0.0245 (4)
H8	0.618437	0.079526	0.788610	0.029*
C9	0.5108 (2)	0.24198 (19)	0.89628 (13)	0.0237 (4)
H9A	0.589661	0.245866	0.906416	0.028*
H9B	0.453931	0.264980	0.943998	0.028*
C10	0.48228 (19)	0.32883 (18)	0.81931 (13)	0.0217 (4)
C11	0.3729 (2)	0.3272 (2)	0.78461 (14)	0.0274 (5)
H11	0.304341	0.300502	0.814352	0.033*
C12	0.3917 (2)	0.3702 (2)	0.70465 (14)	0.0289 (5)
H12	0.340100	0.379979	0.665263	0.035*
C13	0.51173 (19)	0.40013 (19)	0.68953 (13)	0.0230 (4)
C14	0.5869 (2)	0.4180 (2)	0.60650 (13)	0.0266 (5)
H14A	0.652259	0.350464	0.601447	0.032*
H14B	0.540199	0.428583	0.561104	0.032*
C15	0.4833 (2)	0.45976 (19)	0.82203 (13)	0.0271 (5)
H15A	0.407907	0.498358	0.849741	0.032*
H15B	0.547856	0.466503	0.850003	0.032*
C16	0.5028 (2)	0.51120 (19)	0.72882 (13)	0.0262 (5)
H16	0.434974	0.573493	0.712567	0.031*
C17	0.6189 (2)	0.5493 (2)	0.69070 (14)	0.0268 (5)
H17A	0.615310	0.633446	0.691189	0.032*
H17B	0.684024	0.501509	0.719696	0.032*
C18	0.86926 (19)	0.46288 (19)	0.57944 (13)	0.0237 (4)
C19	0.9263 (2)	0.5017 (2)	0.63118 (15)	0.0295 (5)
H19	0.901762	0.579077	0.643101	0.035*
C20	1.0194 (2)	0.4264 (2)	0.66527 (14)	0.0298 (5)
H20	1.059570	0.453139	0.699867	0.036*
C21	1.0548 (2)	0.3122 (2)	0.64953 (14)	0.0268 (5)
C22	0.9972 (2)	0.2756 (2)	0.59696 (14)	0.0257 (5)
H22	1.021707	0.198304	0.584974	0.031*
C23	0.90444 (19)	0.3498 (2)	0.56163 (13)	0.0246 (4)
H23	0.865580	0.323813	0.525833	0.030*
C24	1.1564 (2)	0.2296 (2)	0.68509 (17)	0.0381 (6)
H24A	1.136052	0.151744	0.705618	0.057*
H24B	1.174711	0.259604	0.730684	0.057*
H24C	1.224817	0.223780	0.642151	0.057*
S1'	0.76670 (5)	1.04803 (5)	0.53217 (3)	0.02277 (12)
O1'	1.14505 (15)	0.50110 (16)	0.91923 (11)	0.0362 (4)
O2'	0.76049 (15)	0.54898 (17)	0.93007 (12)	0.0410 (5)
H2'	0.782753	0.534895	0.980589	0.078 (12)*
O3'	0.90933 (13)	0.76045 (13)	0.73711 (9)	0.0234 (3)
O4'	0.80016 (14)	0.99924 (15)	0.45795 (9)	0.0300 (4)
O5'	0.75650 (14)	1.17211 (14)	0.52883 (10)	0.0289 (4)
N1'	0.95957 (17)	0.56602 (18)	0.88347 (12)	0.0302 (4)
N2'	0.86625 (15)	0.98216 (16)	0.59042 (11)	0.0223 (4)
C1'	1.0534 (2)	0.4821 (2)	0.90414 (14)	0.0297 (5)
C2'	1.0214 (2)	0.3675 (2)	0.90349 (14)	0.0306 (5)
C3'	1.0859 (2)	0.2544 (2)	0.91983 (15)	0.0349 (6)
H3'	1.162486	0.240626	0.934224	0.042*
C4'	1.0340 (3)	0.1626 (3)	0.91428 (18)	0.0469 (7)
H4'	1.075607	0.084206	0.925324	0.056*
C5'	0.9228 (3)	0.1828 (3)	0.8930 (2)	0.0513 (8)
H5'	0.889731	0.118235	0.889034	0.062*
C6'	0.8584 (3)	0.2968 (3)	0.87730 (19)	0.0457 (7)
H6'	0.781783	0.310803	0.862951	0.055*
C7'	0.9096 (2)	0.3884 (2)	0.88328 (15)	0.0345 (6)
C8'	0.8596 (2)	0.5185 (2)	0.87297 (16)	0.0350 (6)
H8'	0.840457	0.547981	0.815582	0.042*
C9'	0.9530 (2)	0.6906 (2)	0.87978 (14)	0.0314 (5)
H9'A	1.003483	0.701044	0.917835	0.038*
H9'B	0.871471	0.726203	0.899287	0.038*
C10'	0.98998 (19)	0.7553 (2)	0.79436 (13)	0.0239 (4)
C11'	1.1054 (2)	0.7027 (2)	0.74680 (14)	0.0260 (5)
H11'	1.170278	0.652311	0.769535	0.031*
C12'	1.09712 (19)	0.74141 (19)	0.66761 (14)	0.0251 (5)
H12'	1.154055	0.724037	0.621769	0.030*
C13'	0.97764 (19)	0.81916 (19)	0.66568 (13)	0.0221 (4)
C14'	0.9156 (2)	0.8553 (2)	0.59063 (14)	0.0264 (5)
H14C	0.971028	0.843925	0.539741	0.032*
H14D	0.852747	0.809951	0.595442	0.032*
C15'	0.9874 (2)	0.8886 (2)	0.78895 (13)	0.0255 (5)
H15C	0.918542	0.924993	0.824380	0.031*
H15D	1.059722	0.902498	0.804252	0.031*
C16'	0.97915 (18)	0.93444 (19)	0.69668 (13)	0.0223 (4)
H16'	1.048276	0.970275	0.668076	0.027*
C17'	0.86454 (19)	1.01119 (19)	0.67252 (13)	0.0222 (4)
H17C	0.796071	0.989347	0.711767	0.027*
H17D	0.864683	1.095695	0.668901	0.027*
C18'	0.63222 (18)	1.01004 (19)	0.58149 (13)	0.0226 (4)
C19'	0.6003 (2)	0.9103 (2)	0.56757 (15)	0.0285 (5)
H19'	0.648619	0.865397	0.529054	0.034*
C20'	0.4977 (2)	0.8770 (2)	0.61023 (15)	0.0308 (5)
H20'	0.476141	0.808453	0.601103	0.037*
C21'	0.4257 (2)	0.9424 (2)	0.66633 (14)	0.0293 (5)
C22'	0.4569 (2)	1.0438 (2)	0.67779 (14)	0.0283 (5)
H22'	0.407097	1.090152	0.714863	0.034*
C23'	0.55990 (19)	1.0784 (2)	0.63577 (13)	0.0248 (4)
H23'	0.580717	1.147840	0.643989	0.030*
C24'	0.3143 (2)	0.9045 (3)	0.71372 (16)	0.0400 (6)
H24D	0.285977	0.947062	0.759935	0.060*
H24E	0.330163	0.819809	0.734947	0.060*
H24F	0.254611	0.922022	0.676926	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0286 (3)	0.0229 (3)	0.0220 (3)	−0.0052 (2)	0.0008 (2)	0.0024 (2)
O1	0.0220 (8)	0.0272 (8)	0.0249 (8)	−0.0003 (6)	−0.0020 (6)	0.0004 (6)
O2	0.0233 (8)	0.0326 (9)	0.0245 (8)	−0.0072 (7)	0.0000 (6)	0.0010 (7)
O3	0.0247 (7)	0.0199 (7)	0.0166 (7)	−0.0036 (6)	−0.0020 (6)	0.0007 (5)
O4	0.0367 (10)	0.0216 (8)	0.0409 (10)	−0.0069 (7)	0.0025 (8)	0.0042 (7)
O5	0.0322 (9)	0.0389 (10)	0.0194 (8)	−0.0058 (7)	−0.0017 (7)	0.0023 (7)
N1	0.0260 (9)	0.0207 (9)	0.0175 (8)	−0.0043 (7)	−0.0010 (7)	−0.0003 (7)
N2	0.0269 (9)	0.0236 (9)	0.0188 (9)	−0.0063 (7)	0.0026 (7)	−0.0008 (7)
C1	0.0233 (10)	0.0237 (11)	0.0159 (9)	−0.0033 (8)	−0.0067 (8)	0.0035 (8)
C2	0.0278 (11)	0.0228 (11)	0.0191 (10)	−0.0045 (9)	−0.0076 (8)	0.0015 (8)
C3	0.0327 (12)	0.0272 (12)	0.0253 (11)	−0.0083 (10)	−0.0102 (10)	0.0010 (9)
C4	0.0486 (15)	0.0247 (12)	0.0315 (12)	−0.0112 (11)	−0.0190 (11)	0.0005 (10)
C5	0.0481 (15)	0.0242 (12)	0.0308 (12)	−0.0012 (11)	−0.0153 (11)	−0.0056 (10)
C6	0.0355 (13)	0.0287 (13)	0.0266 (12)	0.0005 (10)	−0.0074 (10)	−0.0043 (9)
C7	0.0291 (11)	0.0249 (11)	0.0170 (10)	−0.0030 (9)	−0.0047 (8)	−0.0013 (8)
C8	0.0254 (11)	0.0266 (11)	0.0179 (10)	−0.0025 (9)	0.0002 (8)	−0.0013 (8)
C9	0.0294 (11)	0.0218 (11)	0.0191 (10)	−0.0056 (9)	−0.0030 (9)	−0.0012 (8)
C10	0.0252 (10)	0.0208 (10)	0.0176 (9)	−0.0045 (8)	−0.0009 (8)	−0.0015 (8)
C11	0.0244 (11)	0.0292 (12)	0.0262 (11)	−0.0067 (9)	−0.0030 (9)	0.0018 (9)
C12	0.0265 (11)	0.0341 (13)	0.0247 (11)	−0.0072 (10)	−0.0071 (9)	0.0027 (9)
C13	0.0280 (11)	0.0201 (10)	0.0181 (10)	−0.0034 (8)	−0.0033 (8)	0.0018 (8)
C14	0.0342 (12)	0.0264 (12)	0.0195 (10)	−0.0110 (9)	−0.0011 (9)	−0.0015 (8)
C15	0.0360 (13)	0.0226 (11)	0.0203 (10)	−0.0070 (9)	0.0042 (9)	−0.0042 (8)
C16	0.0315 (12)	0.0203 (11)	0.0219 (10)	−0.0025 (9)	0.0005 (9)	0.0010 (8)
C17	0.0348 (12)	0.0205 (11)	0.0231 (11)	−0.0080 (9)	0.0015 (9)	−0.0016 (8)
C18	0.0260 (11)	0.0236 (11)	0.0203 (10)	−0.0068 (9)	0.0008 (8)	−0.0027 (8)
C19	0.0336 (12)	0.0250 (12)	0.0320 (12)	−0.0099 (10)	−0.0008 (10)	−0.0082 (9)
C20	0.0343 (13)	0.0346 (13)	0.0267 (11)	−0.0146 (10)	−0.0075 (10)	−0.0081 (10)
C21	0.0258 (11)	0.0324 (13)	0.0220 (11)	−0.0098 (9)	−0.0007 (9)	−0.0021 (9)
C22	0.0282 (11)	0.0237 (11)	0.0252 (11)	−0.0052 (9)	−0.0006 (9)	−0.0063 (9)
C23	0.0261 (11)	0.0269 (12)	0.0236 (11)	−0.0071 (9)	−0.0045 (9)	−0.0074 (9)
C24	0.0322 (13)	0.0454 (16)	0.0372 (14)	−0.0042 (11)	−0.0143 (11)	−0.0033 (12)
S1'	0.0233 (3)	0.0244 (3)	0.0192 (2)	−0.0058 (2)	−0.0031 (2)	0.0010 (2)
O1'	0.0288 (9)	0.0474 (11)	0.0299 (9)	−0.0071 (8)	−0.0058 (7)	0.0000 (8)
O2'	0.0231 (9)	0.0504 (12)	0.0405 (11)	−0.0009 (8)	−0.0048 (8)	0.0061 (8)
O3'	0.0216 (7)	0.0276 (8)	0.0200 (7)	−0.0079 (6)	−0.0011 (6)	−0.0002 (6)
O4'	0.0309 (9)	0.0383 (10)	0.0192 (8)	−0.0050 (7)	−0.0038 (7)	−0.0029 (7)
O5'	0.0312 (9)	0.0232 (8)	0.0311 (9)	−0.0088 (7)	−0.0046 (7)	0.0023 (6)
N1'	0.0264 (10)	0.0315 (11)	0.0270 (10)	−0.0065 (8)	−0.0029 (8)	0.0076 (8)
N2'	0.0214 (9)	0.0258 (10)	0.0188 (8)	−0.0025 (7)	−0.0037 (7)	−0.0031 (7)
C1'	0.0250 (11)	0.0389 (14)	0.0186 (10)	−0.0036 (10)	0.0003 (9)	0.0041 (9)
C2'	0.0254 (11)	0.0362 (14)	0.0245 (11)	−0.0044 (10)	0.0001 (9)	0.0031 (10)
C3'	0.0320 (13)	0.0372 (14)	0.0260 (12)	−0.0002 (11)	0.0043 (10)	0.0019 (10)
C4'	0.0482 (17)	0.0344 (15)	0.0467 (17)	−0.0011 (13)	0.0068 (14)	−0.0007 (12)
C5'	0.0491 (18)	0.0444 (18)	0.060 (2)	−0.0168 (14)	0.0031 (15)	−0.0084 (15)
C6'	0.0356 (15)	0.0487 (18)	0.0520 (17)	−0.0157 (13)	−0.0054 (13)	0.0007 (14)
C7'	0.0292 (12)	0.0395 (15)	0.0292 (12)	−0.0070 (11)	−0.0008 (10)	0.0046 (10)
C8'	0.0248 (12)	0.0422 (15)	0.0323 (13)	−0.0055 (10)	−0.0053 (10)	0.0067 (11)
C9'	0.0330 (13)	0.0342 (13)	0.0224 (11)	−0.0049 (10)	−0.0003 (10)	0.0009 (9)
C10'	0.0222 (10)	0.0295 (12)	0.0185 (10)	−0.0059 (9)	−0.0027 (8)	0.0000 (8)
C11'	0.0236 (11)	0.0256 (11)	0.0267 (11)	−0.0035 (9)	−0.0027 (9)	−0.0017 (9)
C12'	0.0227 (11)	0.0254 (11)	0.0254 (11)	−0.0030 (9)	−0.0006 (9)	−0.0044 (9)
C13'	0.0235 (10)	0.0245 (11)	0.0178 (10)	−0.0066 (8)	−0.0005 (8)	−0.0025 (8)
C14'	0.0311 (12)	0.0262 (12)	0.0228 (11)	−0.0009 (9)	−0.0070 (9)	−0.0080 (9)
C15'	0.0261 (11)	0.0321 (12)	0.0198 (10)	−0.0067 (9)	−0.0049 (9)	−0.0051 (9)
C16'	0.0214 (10)	0.0252 (11)	0.0209 (10)	−0.0074 (8)	−0.0025 (8)	−0.0026 (8)
C17'	0.0239 (10)	0.0227 (11)	0.0200 (10)	−0.0057 (8)	−0.0015 (8)	−0.0041 (8)
C18'	0.0201 (10)	0.0235 (11)	0.0226 (10)	−0.0039 (8)	−0.0058 (8)	0.0017 (8)
C19'	0.0285 (12)	0.0235 (11)	0.0342 (12)	−0.0032 (9)	−0.0086 (10)	−0.0053 (9)
C20'	0.0305 (12)	0.0259 (12)	0.0389 (14)	−0.0104 (10)	−0.0138 (10)	0.0009 (10)
C21'	0.0239 (11)	0.0348 (13)	0.0276 (12)	−0.0092 (9)	−0.0134 (9)	0.0103 (10)
C22'	0.0234 (11)	0.0358 (13)	0.0236 (11)	−0.0022 (9)	−0.0055 (9)	−0.0021 (9)
C23'	0.0248 (11)	0.0257 (11)	0.0239 (11)	−0.0057 (9)	−0.0051 (9)	−0.0021 (8)
C24'	0.0281 (13)	0.0547 (17)	0.0358 (14)	−0.0165 (12)	−0.0121 (11)	0.0109 (12)

Geometric parameters (Å, º)

S1—O4	1.4332 (17)	S1'—O4'	1.4337 (17)
S1—O5	1.4337 (17)	S1'—O5'	1.4378 (17)
S1—N2	1.6368 (19)	S1'—N2'	1.6263 (18)
S1—C18	1.758 (2)	S1'—C18'	1.758 (2)
O1—C1	1.240 (3)	O1'—C1'	1.231 (3)
O2—C8	1.407 (3)	O2'—C8'	1.404 (3)
O2—H2	0.9160	O2'—H2'	0.9026
O3—C10	1.449 (2)	O3'—C13'	1.452 (2)
O3—C13	1.456 (2)	O3'—C10'	1.453 (3)
N1—C1	1.356 (3)	N1'—C1'	1.363 (3)
N1—C9	1.452 (3)	N1'—C9'	1.449 (3)
N1—C8	1.477 (3)	N1'—C8'	1.466 (3)
N2—C17	1.481 (3)	N2'—C17'	1.480 (3)
N2—C14	1.487 (3)	N2'—C14'	1.488 (3)
C1—C2	1.474 (3)	C1'—C2'	1.488 (4)
C2—C7	1.387 (3)	C2'—C7'	1.382 (3)
C2—C3	1.390 (3)	C2'—C3'	1.389 (3)
C3—C4	1.394 (3)	C3'—C4'	1.385 (4)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.391 (4)	C4'—C5'	1.381 (4)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.393 (4)	C5'—C6'	1.396 (4)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.383 (3)	C6'—C7'	1.379 (4)
C6—H6	0.9500	C6'—H6'	0.9500
C7—C8	1.511 (3)	C7'—C8'	1.511 (4)
C8—H8	1.0000	C8'—H8'	1.0000
C9—C10	1.511 (3)	C9'—C10'	1.510 (3)
C9—H9A	0.9900	C9'—H9'A	0.9900
C9—H9B	0.9900	C9'—H9'B	0.9900
C10—C11	1.516 (3)	C10'—C11'	1.526 (3)
C10—C15	1.563 (3)	C10'—C15'	1.557 (3)
C11—C12	1.325 (3)	C11'—C12'	1.323 (3)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.502 (3)	C12'—C13'	1.512 (3)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.509 (3)	C13'—C14'	1.507 (3)
C13—C16	1.565 (3)	C13'—C16'	1.563 (3)
C14—H14A	0.9900	C14'—H14C	0.9900
C14—H14B	0.9900	C14'—H14D	0.9900
C15—C16	1.546 (3)	C15'—C16'	1.540 (3)
C15—H15A	0.9900	C15'—H15C	0.9900
C15—H15B	0.9900	C15'—H15D	0.9900
C16—C17	1.525 (3)	C16'—C17'	1.529 (3)
C16—H16	1.0000	C16'—H16'	1.0000
C17—H17A	0.9900	C17'—H17C	0.9900
C17—H17B	0.9900	C17'—H17D	0.9900
C18—C19	1.388 (3)	C18'—C19'	1.389 (3)
C18—C23	1.391 (3)	C18'—C23'	1.392 (3)
C19—C20	1.387 (3)	C19'—C20'	1.383 (3)
C19—H19	0.9500	C19'—H19'	0.9500
C20—C21	1.392 (3)	C20'—C21'	1.391 (4)
C20—H20	0.9500	C20'—H20'	0.9500
C21—C22	1.389 (3)	C21'—C22'	1.388 (3)
C21—C24	1.504 (3)	C21'—C24'	1.515 (3)
C22—C23	1.387 (3)	C22'—C23'	1.389 (3)
C22—H22	0.9500	C22'—H22'	0.9500
C23—H23	0.9500	C23'—H23'	0.9500
C24—H24A	0.9800	C24'—H24D	0.9800
C24—H24B	0.9800	C24'—H24E	0.9800
C24—H24C	0.9800	C24'—H24F	0.9800
O4—S1—O5	120.45 (10)	O4'—S1'—O5'	120.20 (10)
O4—S1—N2	106.71 (10)	O4'—S1'—N2'	105.39 (10)
O5—S1—N2	105.53 (10)	O5'—S1'—N2'	106.73 (10)
O4—S1—C18	107.32 (11)	O4'—S1'—C18'	108.51 (10)
O5—S1—C18	109.11 (10)	O5'—S1'—C18'	107.32 (10)
N2—S1—C18	107.01 (10)	N2'—S1'—C18'	108.20 (10)
C8—O2—H2	108.3	C8'—O2'—H2'	108.3
C10—O3—C13	95.72 (15)	C13'—O3'—C10'	95.37 (15)
C1—N1—C9	123.97 (18)	C1'—N1'—C9'	123.9 (2)
C1—N1—C8	113.04 (18)	C1'—N1'—C8'	113.8 (2)
C9—N1—C8	122.98 (17)	C9'—N1'—C8'	122.0 (2)
C17—N2—C14	109.96 (16)	C17'—N2'—C14'	110.14 (16)
C17—N2—S1	119.69 (15)	C17'—N2'—S1'	121.96 (14)
C14—N2—S1	118.46 (14)	C14'—N2'—S1'	119.12 (14)
O1—C1—N1	125.2 (2)	O1'—C1'—N1'	125.3 (2)
O1—C1—C2	127.7 (2)	O1'—C1'—C2'	128.7 (2)
N1—C1—C2	107.04 (18)	N1'—C1'—C2'	106.0 (2)
C7—C2—C3	121.9 (2)	C7'—C2'—C3'	121.8 (2)
C7—C2—C1	108.71 (19)	C7'—C2'—C1'	108.7 (2)
C3—C2—C1	129.4 (2)	C3'—C2'—C1'	129.6 (2)
C2—C3—C4	117.1 (2)	C4'—C3'—C2'	117.2 (3)
C2—C3—H3	121.5	C4'—C3'—H3'	121.4
C4—C3—H3	121.5	C2'—C3'—H3'	121.4
C5—C4—C3	120.9 (2)	C5'—C4'—C3'	121.3 (3)
C5—C4—H4	119.5	C5'—C4'—H4'	119.3
C3—C4—H4	119.5	C3'—C4'—H4'	119.3
C4—C5—C6	121.5 (2)	C4'—C5'—C6'	121.0 (3)
C4—C5—H5	119.2	C4'—C5'—H5'	119.5
C6—C5—H5	119.2	C6'—C5'—H5'	119.5
C7—C6—C5	117.5 (2)	C7'—C6'—C5'	117.8 (3)
C7—C6—H6	121.3	C7'—C6'—H6'	121.1
C5—C6—H6	121.3	C5'—C6'—H6'	121.1
C6—C7—C2	121.1 (2)	C6'—C7'—C2'	120.8 (3)
C6—C7—C8	129.4 (2)	C6'—C7'—C8'	129.4 (2)
C2—C7—C8	109.48 (19)	C2'—C7'—C8'	109.8 (2)
O2—C8—N1	112.16 (17)	O2'—C8'—N1'	112.0 (2)
O2—C8—C7	114.70 (18)	O2'—C8'—C7'	114.4 (2)
N1—C8—C7	101.68 (17)	N1'—C8'—C7'	101.48 (19)
O2—C8—H8	109.3	O2'—C8'—H8'	109.6
N1—C8—H8	109.3	N1'—C8'—H8'	109.6
C7—C8—H8	109.3	C7'—C8'—H8'	109.6
N1—C9—C10	113.26 (17)	N1'—C9'—C10'	113.6 (2)
N1—C9—H9A	108.9	N1'—C9'—H9'A	108.9
C10—C9—H9A	108.9	C10'—C9'—H9'A	108.9
N1—C9—H9B	108.9	N1'—C9'—H9'B	108.9
C10—C9—H9B	108.9	C10'—C9'—H9'B	108.9
H9A—C9—H9B	107.7	H9'A—C9'—H9'B	107.7
O3—C10—C9	111.77 (17)	O3'—C10'—C9'	112.69 (18)
O3—C10—C11	101.29 (16)	O3'—C10'—C11'	100.79 (17)
C9—C10—C11	118.54 (18)	C9'—C10'—C11'	117.59 (19)
O3—C10—C15	100.25 (15)	O3'—C10'—C15'	100.44 (16)
C9—C10—C15	115.28 (18)	C9'—C10'—C15'	114.75 (19)
C11—C10—C15	107.33 (18)	C11'—C10'—C15'	108.40 (18)
C12—C11—C10	106.5 (2)	C12'—C11'—C10'	106.32 (19)
C12—C11—H11	126.7	C12'—C11'—H11'	126.8
C10—C11—H11	126.7	C10'—C11'—H11'	126.8
C11—C12—C13	105.4 (2)	C11'—C12'—C13'	105.22 (19)
C11—C12—H12	127.3	C11'—C12'—H12'	127.4
C13—C12—H12	127.3	C13'—C12'—H12'	127.4
O3—C13—C12	102.11 (16)	O3'—C13'—C14'	113.05 (18)
O3—C13—C14	111.92 (18)	O3'—C13'—C12'	101.73 (16)
C12—C13—C14	125.30 (19)	C14'—C13'—C12'	124.03 (19)
O3—C13—C16	100.04 (16)	O3'—C13'—C16'	99.92 (16)
C12—C13—C16	107.30 (18)	C14'—C13'—C16'	106.76 (17)
C14—C13—C16	107.29 (17)	C12'—C13'—C16'	108.74 (17)
N2—C14—C13	103.49 (17)	N2'—C14'—C13'	103.46 (17)
N2—C14—H14A	111.1	N2'—C14'—H14C	111.1
C13—C14—H14A	111.1	C13'—C14'—H14C	111.1
N2—C14—H14B	111.1	N2'—C14'—H14D	111.1
C13—C14—H14B	111.1	C13'—C14'—H14D	111.1
H14A—C14—H14B	109.0	H14C—C14'—H14D	109.0
C16—C15—C10	100.84 (17)	C16'—C15'—C10'	100.90 (17)
C16—C15—H15A	111.6	C16'—C15'—H15C	111.6
C10—C15—H15A	111.6	C10'—C15'—H15C	111.6
C16—C15—H15B	111.6	C16'—C15'—H15D	111.6
C10—C15—H15B	111.6	C10'—C15'—H15D	111.6
H15A—C15—H15B	109.4	H15C—C15'—H15D	109.4
C17—C16—C15	119.1 (2)	C17'—C16'—C15'	118.39 (18)
C17—C16—C13	101.38 (17)	C17'—C16'—C13'	101.21 (16)
C15—C16—C13	101.55 (17)	C15'—C16'—C13'	101.62 (17)
C17—C16—H16	111.2	C17'—C16'—H16'	111.5
C15—C16—H16	111.2	C15'—C16'—H16'	111.5
C13—C16—H16	111.2	C13'—C16'—H16'	111.5
N2—C17—C16	101.58 (18)	N2'—C17'—C16'	100.82 (16)
N2—C17—H17A	111.5	N2'—C17'—H17C	111.6
C16—C17—H17A	111.5	C16'—C17'—H17C	111.6
N2—C17—H17B	111.5	N2'—C17'—H17D	111.6
C16—C17—H17B	111.5	C16'—C17'—H17D	111.6
H17A—C17—H17B	109.3	H17C—C17'—H17D	109.4
C19—C18—C23	120.8 (2)	C19'—C18'—C23'	120.5 (2)
C19—C18—S1	120.11 (18)	C19'—C18'—S1'	119.70 (17)
C23—C18—S1	119.01 (17)	C23'—C18'—S1'	119.76 (17)
C20—C19—C18	119.2 (2)	C20'—C19'—C18'	119.4 (2)
C20—C19—H19	120.4	C20'—C19'—H19'	120.3
C18—C19—H19	120.4	C18'—C19'—H19'	120.3
C19—C20—C21	121.0 (2)	C19'—C20'—C21'	120.9 (2)
C19—C20—H20	119.5	C19'—C20'—H20'	119.5
C21—C20—H20	119.5	C21'—C20'—H20'	119.5
C22—C21—C20	118.8 (2)	C22'—C21'—C20'	119.0 (2)
C22—C21—C24	119.4 (2)	C22'—C21'—C24'	120.3 (2)
C20—C21—C24	121.7 (2)	C20'—C21'—C24'	120.7 (2)
C23—C22—C21	121.2 (2)	C21'—C22'—C23'	120.9 (2)
C23—C22—H22	119.4	C21'—C22'—H22'	119.6
C21—C22—H22	119.4	C23'—C22'—H22'	119.6
C22—C23—C18	119.0 (2)	C22'—C23'—C18'	119.2 (2)
C22—C23—H23	120.5	C22'—C23'—H23'	120.4
C18—C23—H23	120.5	C18'—C23'—H23'	120.4
C21—C24—H24A	109.5	C21'—C24'—H24D	109.5
C21—C24—H24B	109.5	C21'—C24'—H24E	109.5
H24A—C24—H24B	109.5	H24D—C24'—H24E	109.5
C21—C24—H24C	109.5	C21'—C24'—H24F	109.5
H24A—C24—H24C	109.5	H24D—C24'—H24F	109.5
H24B—C24—H24C	109.5	H24E—C24'—H24F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	1.00	2.63	3.206 (3)	117
C12—H12···O5^i	0.95	2.47	3.333 (3)	151
C14—H14A···O5′^ii	0.99	2.62	3.506 (3)	149
C23—H23···O5′^ii	0.95	2.41	3.195 (3)	139
C14′—H14D···O4	0.99	2.58	3.482 (3)	151
C15′—H15C···O2^iii	0.99	2.62	3.585 (3)	165
C16′—H16′···O4′^iv	1.00	2.53	3.422 (3)	149
C19′—H19′···O4	0.95	2.34	3.078 (3)	134
O2—H2···O1^v	0.92	1.85	2.756 (2)	172
O2′—H2′···O1′^vi	0.90	1.95	2.840 (3)	171

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