The crystal structures of 3-O-benzyl-1,2-O-iso­propyl­idene-5-O-methane­sulfonyl-6-O-tri­phenyl­methyl-α-D-gluco­furan­ose and its azide displacement product

The effect of different leaving groups on the substitution versus elimination outcomes with C-5 D-glucose derivatives was investigated.

Key indicators

Structure: 3

• Single-crystal X-ray study
• T = 190 K
• Mean [sigma](C-C) = 0.018 Å
• R factor = 0.094
• wR factor = 0.351
• Data-to-parameter ratio = 14.5

Structure: 4

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.085
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Datablock: 3


Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level B
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.01809 Ang.

Alert level C
PLAT084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.35 Report
PLAT213_ALERT_2_C Atom C36             has ADP max/min Ratio .....        3.2 prolat
PLAT234_ALERT_4_C Large Hirshfeld Difference S1       --C36              0.20 Ang.
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         C7 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.882 Check
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.95A   From O6             -0.47 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H5               -0.34 eA-3

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.17 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.01 Why ?
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O6             119.8 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             109.3 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             109.2 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             105.6 Degree
PLAT791_ALERT_4_G Model has Chirality at C1          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Chiral SPGR)          R Verify
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        51% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

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




Datablock: 4


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for   N1       --N2        .        5.2 s.u.

Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00020 Ang.
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             107.6 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             109.6 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             107.9 Degree
PLAT791_ALERT_4_G Model has Chirality at C1          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Chiral SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

   0 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
   0 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


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: CrysAlis PRO (Rigaku OD, 2015) for (3); CrysAlis PRO (Agilent, 2015) for (4). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (3); CrysAlis PRO (Agilent, 2015) for (4). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (3); CrysAlis PRO (Agilent, 2015) for (4). Program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a) for (3); SIR97 (Altomare et al., 1999) for (4). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b) for (3); SHELXL2018 (Sheldrick, 2015b) for (4). For both structures, molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b) and publCIF (Westrip, 2010) for (3); SHELXL2018 (Sheldrick, 2015b) and publCIF (Westrip, 2010) for (4).

1-[(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(trityloxy)ethyl methanesulfonate (3)

Crystal data

C36H38O8S	Dx = 1.284 Mg m^−3
Mr = 630.72	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 10052 reflections
a = 10.0069 (5) Å	θ = 4.5–70.0°
b = 10.1898 (7) Å	µ = 1.31 mm^−1
c = 32.0045 (14) Å	T = 190 K
V = 3263.4 (3) Å^3	Block, colourless
Z = 4	0.3 × 0.25 × 0.2 mm
F(000) = 1336

Data collection

Rigaku Xcalibur, Sapphire3, Gemini ultra diffractometer	4263 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	Rint = 0.068
ω scans	θmax = 68.0°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −11→12
Tmin = 0.840, Tmax = 1.000	k = −12→12
20834 measured reflections	l = −33→38
5928 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.094	w = 1/[σ^2(Fo^2) + (0.1748P)^2 + 6.0087P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.351	(Δ/σ)max < 0.001
S = 1.20	Δρmax = 0.53 e Å^−3
5928 reflections	Δρmin = −1.07 e Å^−3
410 parameters	Extinction correction: (SHELXL-2018/3; Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0044 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 1367 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.004 (10)

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	0.5662 (3)	0.7854 (3)	0.46165 (7)	0.0576 (8)
O1	0.5510 (8)	0.6791 (7)	0.31101 (19)	0.0566 (19)
O2	0.6330 (10)	0.7335 (8)	0.2462 (2)	0.067 (2)
O3	0.6539 (9)	0.9404 (8)	0.2696 (2)	0.065 (2)
O4	0.4019 (8)	0.8917 (7)	0.3505 (2)	0.0550 (18)
O5	0.7705 (7)	0.5716 (7)	0.3878 (2)	0.0485 (16)
O6	0.6203 (9)	0.7925 (8)	0.4151 (2)	0.063 (2)
O7	0.4808 (9)	0.6727 (8)	0.4660 (2)	0.068 (2)
O8	0.5109 (13)	0.9099 (9)	0.4710 (3)	0.094 (4)
C1	0.5280 (14)	0.7491 (10)	0.2743 (3)	0.059 (3)
H1	0.440997	0.723237	0.261309	0.071*
C2	0.5292 (13)	0.8954 (11)	0.2854 (3)	0.058 (3)
H2	0.450815	0.944503	0.273966	0.069*
C3	0.5350 (13)	0.8960 (11)	0.3333 (3)	0.055 (3)
H3	0.587619	0.971936	0.344310	0.067*
C4	0.6029 (13)	0.7660 (10)	0.3421 (3)	0.053 (3)
H4	0.701972	0.774736	0.339075	0.064*
C5	0.5684 (13)	0.7023 (10)	0.3837 (3)	0.053 (2)
H5	0.468940	0.698638	0.386460	0.063*
C6	0.6231 (10)	0.5655 (10)	0.3885 (3)	0.047 (2)
H6A	0.592268	0.527018	0.415221	0.056*
H6B	0.590666	0.509275	0.365389	0.056*
C7	0.6830 (14)	0.8585 (12)	0.2349 (3)	0.064 (3)
C8	0.8334 (18)	0.850 (2)	0.2300 (6)	0.110 (6)
H8A	0.855493	0.777777	0.210871	0.166*
H8B	0.874231	0.832793	0.257338	0.166*
H8C	0.867575	0.932418	0.218739	0.166*
C9	0.613 (2)	0.9036 (15)	0.1955 (4)	0.094 (5)
H9A	0.641165	0.993113	0.188667	0.141*
H9B	0.515871	0.902173	0.199947	0.141*
H9C	0.635774	0.844726	0.172374	0.141*
C10	0.3419 (15)	1.0193 (11)	0.3553 (4)	0.065 (3)
H10A	0.332671	1.062316	0.327718	0.077*
H10B	0.398722	1.075298	0.373260	0.077*
C11	0.2042 (14)	1.0014 (11)	0.3753 (3)	0.061 (3)
C12	0.1939 (17)	1.0081 (14)	0.4184 (4)	0.073 (4)
H12	0.270576	1.021812	0.435373	0.088*
C13	0.067 (2)	0.9940 (17)	0.4362 (5)	0.103 (6)
H13	0.056333	0.998517	0.465700	0.123*
C14	−0.043 (2)	0.9736 (17)	0.4108 (7)	0.104 (6)
H14	−0.128897	0.965806	0.423079	0.125*
C15	−0.0304 (19)	0.9644 (15)	0.3689 (5)	0.091 (5)
H15	−0.106376	0.948442	0.351806	0.109*
C16	0.0966 (17)	0.9787 (13)	0.3510 (4)	0.078 (4)
H16	0.106929	0.972430	0.321586	0.093*
C17	0.8331 (11)	0.4437 (10)	0.3839 (3)	0.048 (2)
C18	0.8224 (12)	0.3951 (11)	0.3388 (3)	0.054 (3)
C19	0.8348 (13)	0.2635 (11)	0.3285 (3)	0.061 (3)
H19	0.844259	0.200026	0.350075	0.074*
C20	0.8336 (15)	0.2237 (14)	0.2869 (4)	0.073 (3)
H20	0.844730	0.133531	0.280225	0.088*
C21	0.8166 (15)	0.3136 (14)	0.2555 (3)	0.073 (4)
H21	0.812525	0.285769	0.227217	0.087*
C22	0.8054 (14)	0.4445 (13)	0.2654 (3)	0.065 (3)
H22	0.795842	0.507915	0.243796	0.078*
C23	0.8081 (12)	0.4834 (13)	0.3065 (3)	0.059 (3)
H23	0.799835	0.574119	0.312841	0.071*
C24	0.9853 (12)	0.4693 (9)	0.3914 (3)	0.049 (2)
C25	1.0686 (12)	0.3622 (10)	0.3967 (3)	0.054 (3)
H25	1.033200	0.275944	0.394830	0.065*
C26	1.2063 (13)	0.3806 (12)	0.4050 (3)	0.061 (3)
H26	1.263470	0.307176	0.408860	0.073*
C27	1.2568 (14)	0.5071 (14)	0.4073 (4)	0.068 (3)
H27	1.348633	0.520765	0.413357	0.081*
C28	1.1724 (15)	0.6145 (13)	0.4007 (4)	0.074 (3)
H28	1.207834	0.701004	0.401258	0.089*
C29	1.0347 (13)	0.5951 (12)	0.3931 (4)	0.063 (3)
H29	0.976890	0.668086	0.389262	0.075*
C30	0.7800 (13)	0.3519 (11)	0.4171 (3)	0.056 (3)
C31	0.8290 (14)	0.3567 (11)	0.4578 (3)	0.062 (3)
H31	0.899595	0.415396	0.464453	0.074*
C32	0.7762 (16)	0.2769 (14)	0.4887 (3)	0.073 (4)
H32	0.812262	0.281411	0.516140	0.088*
C33	0.6711 (16)	0.1897 (14)	0.4807 (4)	0.078 (4)
H33	0.636079	0.134670	0.501964	0.093*
C34	0.6204 (16)	0.1868 (14)	0.4406 (4)	0.075 (4)
H34	0.548702	0.128922	0.434386	0.090*
C35	0.6703 (13)	0.2649 (11)	0.4096 (3)	0.062 (3)
H35	0.631387	0.261348	0.382575	0.075*
C36	0.7142 (14)	0.763 (2)	0.4884 (5)	0.115 (7)
H36A	0.696895	0.766101	0.518575	0.173*
H36B	0.777068	0.833003	0.480916	0.173*
H36C	0.752616	0.677798	0.481073	0.173*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0813 (18)	0.0600 (15)	0.0316 (11)	−0.0056 (14)	0.0007 (12)	−0.0015 (10)
O1	0.084 (5)	0.053 (4)	0.033 (3)	0.001 (4)	0.000 (3)	0.001 (3)
O2	0.100 (6)	0.057 (4)	0.044 (4)	0.005 (4)	0.019 (4)	0.002 (3)
O3	0.087 (6)	0.060 (4)	0.050 (4)	−0.006 (4)	0.024 (4)	0.004 (3)
O4	0.077 (5)	0.047 (4)	0.041 (3)	0.004 (4)	0.007 (3)	0.002 (3)
O5	0.052 (4)	0.052 (4)	0.042 (3)	0.004 (3)	−0.001 (3)	0.001 (3)
O6	0.094 (6)	0.063 (4)	0.031 (3)	−0.007 (4)	0.000 (3)	0.003 (3)
O7	0.097 (6)	0.061 (4)	0.046 (4)	−0.024 (4)	0.012 (4)	0.002 (3)
O8	0.145 (10)	0.067 (5)	0.072 (6)	0.009 (6)	0.041 (6)	−0.010 (4)
C1	0.090 (8)	0.055 (6)	0.032 (4)	−0.001 (6)	−0.007 (5)	0.002 (4)
C2	0.082 (8)	0.063 (6)	0.029 (4)	0.000 (6)	0.004 (5)	0.006 (4)
C3	0.082 (8)	0.052 (6)	0.032 (4)	−0.002 (6)	0.011 (5)	0.000 (4)
C4	0.077 (7)	0.052 (6)	0.031 (4)	0.003 (5)	−0.001 (4)	0.005 (4)
C5	0.078 (7)	0.048 (5)	0.032 (4)	0.015 (5)	−0.003 (5)	0.002 (4)
C6	0.048 (5)	0.057 (6)	0.036 (4)	−0.002 (4)	0.005 (4)	0.006 (4)
C7	0.078 (8)	0.069 (7)	0.044 (5)	0.006 (6)	0.023 (5)	0.005 (5)
C8	0.095 (12)	0.132 (15)	0.104 (12)	0.016 (12)	0.041 (10)	−0.009 (11)
C9	0.149 (15)	0.087 (10)	0.047 (6)	0.030 (10)	0.023 (8)	0.012 (6)
C10	0.094 (9)	0.045 (6)	0.055 (6)	0.003 (6)	0.003 (6)	−0.004 (5)
C11	0.087 (9)	0.051 (6)	0.044 (5)	0.010 (6)	0.019 (6)	0.000 (5)
C12	0.097 (10)	0.071 (8)	0.053 (6)	0.012 (7)	0.012 (7)	0.003 (6)
C13	0.145 (17)	0.094 (11)	0.069 (8)	0.038 (12)	0.053 (11)	0.025 (8)
C14	0.097 (13)	0.088 (11)	0.127 (14)	0.010 (10)	0.055 (12)	0.030 (10)
C15	0.101 (12)	0.070 (9)	0.102 (11)	−0.003 (8)	0.024 (10)	0.008 (8)
C16	0.113 (12)	0.068 (8)	0.052 (6)	0.019 (8)	−0.003 (7)	−0.004 (6)
C17	0.060 (6)	0.049 (5)	0.035 (4)	0.003 (5)	−0.009 (4)	0.004 (4)
C18	0.068 (7)	0.060 (6)	0.033 (4)	−0.007 (5)	−0.001 (4)	−0.001 (4)
C19	0.081 (8)	0.058 (7)	0.044 (5)	−0.007 (6)	−0.003 (5)	0.001 (5)
C20	0.096 (10)	0.069 (7)	0.054 (6)	−0.005 (7)	−0.004 (6)	−0.020 (6)
C21	0.084 (9)	0.095 (10)	0.039 (5)	0.001 (8)	−0.008 (6)	−0.011 (6)
C22	0.078 (8)	0.079 (8)	0.038 (5)	0.019 (7)	−0.006 (5)	−0.002 (5)
C23	0.067 (7)	0.070 (7)	0.040 (5)	0.008 (6)	0.007 (5)	0.003 (5)
C24	0.070 (7)	0.045 (5)	0.031 (4)	−0.005 (5)	0.005 (4)	0.006 (4)
C25	0.076 (7)	0.048 (5)	0.039 (5)	−0.005 (5)	−0.009 (5)	0.005 (4)
C26	0.078 (8)	0.069 (7)	0.037 (5)	−0.001 (6)	−0.009 (5)	0.003 (5)
C27	0.069 (8)	0.082 (8)	0.053 (6)	−0.009 (7)	−0.010 (6)	0.002 (6)
C28	0.085 (9)	0.060 (7)	0.076 (8)	−0.011 (7)	−0.011 (7)	−0.002 (6)
C29	0.069 (7)	0.057 (6)	0.063 (7)	−0.007 (6)	−0.011 (6)	0.000 (5)
C30	0.083 (8)	0.049 (6)	0.036 (5)	0.003 (5)	0.001 (5)	−0.002 (4)
C31	0.086 (8)	0.059 (6)	0.040 (5)	−0.005 (6)	−0.001 (5)	0.004 (5)
C32	0.102 (10)	0.083 (8)	0.035 (5)	−0.010 (8)	0.002 (6)	0.004 (5)
C33	0.101 (11)	0.084 (9)	0.048 (6)	−0.022 (8)	0.010 (6)	0.008 (6)
C34	0.092 (10)	0.076 (8)	0.055 (6)	−0.011 (7)	−0.008 (6)	0.011 (6)
C35	0.080 (8)	0.058 (6)	0.050 (5)	−0.016 (6)	−0.018 (5)	0.010 (5)
C36	0.055 (8)	0.22 (2)	0.075 (9)	−0.033 (11)	−0.040 (7)	0.051 (12)

Geometric parameters (Å, º)

S1—O8	1.416 (10)	C14—C15	1.35 (2)
S1—O7	1.438 (8)	C14—H14	0.9500
S1—O6	1.587 (7)	C15—C16	1.40 (2)
S1—C36	1.726 (12)	C15—H15	0.9500
O1—C1	1.394 (11)	C16—H16	0.9500
O1—C4	1.429 (12)	C17—C30	1.512 (14)
O2—C1	1.392 (14)	C17—C18	1.528 (13)
O2—C7	1.415 (14)	C17—C24	1.564 (16)
O3—C7	1.419 (13)	C18—C23	1.378 (15)
O3—C2	1.423 (14)	C18—C19	1.386 (16)
O4—C10	1.441 (13)	C19—C20	1.393 (15)
O4—C3	1.441 (14)	C19—H19	0.9500
O5—C17	1.452 (12)	C20—C21	1.370 (18)
O5—C6	1.477 (12)	C20—H20	0.9500
O6—C5	1.457 (12)	C21—C22	1.375 (18)
C1—C2	1.533 (16)	C21—H21	0.9500
C1—H1	1.0000	C22—C23	1.375 (14)
C2—C3	1.533 (12)	C22—H22	0.9500
C2—H2	1.0000	C23—H23	0.9500
C3—C4	1.515 (15)	C24—C29	1.375 (15)
C3—H3	1.0000	C24—C25	1.383 (15)
C4—C5	1.521 (12)	C25—C26	1.416 (17)
C4—H4	1.0000	C25—H25	0.9500
C5—C6	1.506 (14)	C26—C27	1.386 (18)
C5—H5	1.0000	C26—H26	0.9500
C6—H6A	0.9900	C27—C28	1.40 (2)
C6—H6B	0.9900	C27—H27	0.9500
C7—C8	1.52 (2)	C28—C29	1.413 (19)
C7—C9	1.515 (19)	C28—H28	0.9500
C8—H8A	0.9800	C29—H29	0.9500
C8—H8B	0.9800	C30—C31	1.394 (15)
C8—H8C	0.9800	C30—C35	1.431 (16)
C9—H9A	0.9800	C31—C32	1.386 (16)
C9—H9B	0.9800	C31—H31	0.9500
C9—H9C	0.9800	C32—C33	1.401 (19)
C10—C11	1.530 (18)	C32—H32	0.9500
C10—H10A	0.9900	C33—C34	1.379 (17)
C10—H10B	0.9900	C33—H33	0.9500
C11—C16	1.35 (2)	C34—C35	1.366 (17)
C11—C12	1.385 (15)	C34—H34	0.9500
C12—C13	1.40 (2)	C35—H35	0.9500
C12—H12	0.9500	C36—H36A	0.9800
C13—C14	1.38 (3)	C36—H36B	0.9800
C13—H13	0.9500	C36—H36C	0.9800
O8—S1—O7	117.5 (6)	C14—C13—C12	119.8 (14)
O8—S1—O6	106.9 (5)	C14—C13—H13	120.1
O7—S1—O6	109.3 (4)	C12—C13—H13	120.1
O8—S1—C36	110.3 (10)	C15—C14—C13	121.5 (16)
O7—S1—C36	110.9 (8)	C15—C14—H14	119.3
O6—S1—C36	100.4 (7)	C13—C14—H14	119.3
C1—O1—C4	109.3 (8)	C14—C15—C16	118.8 (18)
C1—O2—C7	109.2 (8)	C14—C15—H15	120.6
C7—O3—C2	105.6 (9)	C16—C15—H15	120.6
C10—O4—C3	113.5 (8)	C11—C16—C15	120.5 (13)
C17—O5—C6	113.2 (8)	C11—C16—H16	119.8
C5—O6—S1	119.7 (7)	C15—C16—H16	119.8
O2—C1—O1	111.2 (10)	O5—C17—C30	110.0 (8)
O2—C1—C2	104.8 (9)	O5—C17—C18	110.0 (8)
O1—C1—C2	107.4 (8)	C30—C17—C18	116.0 (9)
O2—C1—H1	111.1	O5—C17—C24	104.9 (8)
O1—C1—H1	111.1	C30—C17—C24	109.8 (8)
C2—C1—H1	111.1	C18—C17—C24	105.5 (8)
O3—C2—C3	108.8 (9)	C23—C18—C19	117.6 (9)
O3—C2—C1	103.7 (10)	C23—C18—C17	120.3 (10)
C3—C2—C1	103.7 (8)	C19—C18—C17	122.0 (9)
O3—C2—H2	113.3	C18—C19—C20	120.5 (11)
C3—C2—H2	113.3	C18—C19—H19	119.7
C1—C2—H2	113.3	C20—C19—H19	119.7
O4—C3—C4	108.5 (9)	C21—C20—C19	120.5 (12)
O4—C3—C2	110.2 (10)	C21—C20—H20	119.7
C4—C3—C2	101.5 (8)	C19—C20—H20	119.7
O4—C3—H3	112.0	C20—C21—C22	119.4 (10)
C4—C3—H3	112.0	C20—C21—H21	120.3
C2—C3—H3	112.0	C22—C21—H21	120.3
O1—C4—C3	104.4 (8)	C23—C22—C21	119.8 (11)
O1—C4—C5	105.3 (8)	C23—C22—H22	120.1
C3—C4—C5	115.7 (9)	C21—C22—H22	120.1
O1—C4—H4	110.4	C22—C23—C18	122.2 (11)
C3—C4—H4	110.4	C22—C23—H23	118.9
C5—C4—H4	110.4	C18—C23—H23	118.9
O6—C5—C6	112.7 (8)	C29—C24—C25	120.9 (11)
O6—C5—C4	104.7 (8)	C29—C24—C17	120.8 (10)
C6—C5—C4	113.6 (8)	C25—C24—C17	118.3 (9)
O6—C5—H5	108.6	C24—C25—C26	120.4 (10)
C6—C5—H5	108.6	C24—C25—H25	119.8
C4—C5—H5	108.6	C26—C25—H25	119.8
O5—C6—C5	108.8 (9)	C27—C26—C25	119.2 (12)
O5—C6—H6A	109.9	C27—C26—H26	120.4
C5—C6—H6A	109.9	C25—C26—H26	120.4
O5—C6—H6B	109.9	C26—C27—C28	120.0 (13)
C5—C6—H6B	109.9	C26—C27—H27	120.0
H6A—C6—H6B	108.3	C28—C27—H27	120.0
O2—C7—O3	104.9 (8)	C27—C28—C29	120.3 (12)
O2—C7—C8	108.9 (12)	C27—C28—H28	119.8
O3—C7—C8	108.6 (12)	C29—C28—H28	119.8
O2—C7—C9	108.7 (12)	C24—C29—C28	119.2 (12)
O3—C7—C9	112.1 (10)	C24—C29—H29	120.4
C8—C7—C9	113.2 (12)	C28—C29—H29	120.4
C7—C8—H8A	109.5	C31—C30—C35	116.5 (10)
C7—C8—H8B	109.5	C31—C30—C17	120.8 (11)
H8A—C8—H8B	109.5	C35—C30—C17	122.4 (9)
C7—C8—H8C	109.5	C32—C31—C30	120.9 (12)
H8A—C8—H8C	109.5	C32—C31—H31	119.5
H8B—C8—H8C	109.5	C30—C31—H31	119.5
C7—C9—H9A	109.5	C31—C32—C33	121.8 (11)
C7—C9—H9B	109.5	C31—C32—H32	119.1
H9A—C9—H9B	109.5	C33—C32—H32	119.1
C7—C9—H9C	109.5	C34—C33—C32	117.5 (11)
H9A—C9—H9C	109.5	C34—C33—H33	121.3
H9B—C9—H9C	109.5	C32—C33—H33	121.3
O4—C10—C11	108.3 (9)	C35—C34—C33	121.9 (13)
O4—C10—H10A	110.0	C35—C34—H34	119.1
C11—C10—H10A	110.0	C33—C34—H34	119.1
O4—C10—H10B	110.0	C34—C35—C30	121.4 (11)
C11—C10—H10B	110.0	C34—C35—H35	119.3
H10A—C10—H10B	108.4	C30—C35—H35	119.3
C16—C11—C12	121.6 (13)	S1—C36—H36A	109.5
C16—C11—C10	119.8 (10)	S1—C36—H36B	109.5
C12—C11—C10	118.6 (13)	H36A—C36—H36B	109.5
C11—C12—C13	117.9 (16)	S1—C36—H36C	109.5
C11—C12—H12	121.0	H36A—C36—H36C	109.5
C13—C12—H12	121.0	H36B—C36—H36C	109.5
O8—S1—O6—C5	−121.0 (9)	C12—C11—C16—C15	2 (2)
O7—S1—O6—C5	7.2 (10)	C10—C11—C16—C15	−178.9 (12)
C36—S1—O6—C5	123.9 (11)	C14—C15—C16—C11	0 (2)
C7—O2—C1—O1	−124.4 (10)	C6—O5—C17—C30	−52.7 (10)
C7—O2—C1—C2	−8.6 (12)	C6—O5—C17—C18	76.3 (10)
C4—O1—C1—O2	98.3 (10)	C6—O5—C17—C24	−170.7 (7)
C4—O1—C1—C2	−15.9 (13)	O5—C17—C18—C23	24.5 (15)
C7—O3—C2—C3	139.1 (9)	C30—C17—C18—C23	150.2 (11)
C7—O3—C2—C1	29.2 (10)	C24—C17—C18—C23	−88.1 (12)
O2—C1—C2—O3	−12.7 (10)	O5—C17—C18—C19	−159.6 (11)
O1—C1—C2—O3	105.7 (10)	C30—C17—C18—C19	−33.9 (16)
O2—C1—C2—C3	−126.4 (9)	C24—C17—C18—C19	87.8 (13)
O1—C1—C2—C3	−7.9 (14)	C23—C18—C19—C20	0 (2)
C10—O4—C3—C4	162.6 (8)	C17—C18—C19—C20	−175.6 (12)
C10—O4—C3—C2	−87.1 (11)	C18—C19—C20—C21	−2 (2)
O3—C2—C3—O4	161.9 (8)	C19—C20—C21—C22	2 (2)
C1—C2—C3—O4	−88.1 (11)	C20—C21—C22—C23	−2 (2)
O3—C2—C3—C4	−83.3 (11)	C21—C22—C23—C18	0 (2)
C1—C2—C3—C4	26.6 (12)	C19—C18—C23—C22	0.3 (19)
C1—O1—C4—C3	33.7 (12)	C17—C18—C23—C22	176.4 (12)
C1—O1—C4—C5	156.0 (9)	O5—C17—C24—C29	−10.1 (12)
O4—C3—C4—O1	79.5 (9)	C30—C17—C24—C29	−128.3 (10)
C2—C3—C4—O1	−36.6 (11)	C18—C17—C24—C29	106.0 (11)
O4—C3—C4—C5	−35.7 (12)	O5—C17—C24—C25	169.0 (8)
C2—C3—C4—C5	−151.8 (10)	C30—C17—C24—C25	50.9 (11)
S1—O6—C5—C6	−75.2 (11)	C18—C17—C24—C25	−74.8 (10)
S1—O6—C5—C4	160.9 (8)	C29—C24—C25—C26	1.3 (15)
O1—C4—C5—O6	−179.3 (9)	C17—C24—C25—C26	−177.9 (9)
C3—C4—C5—O6	−64.6 (12)	C24—C25—C26—C27	−0.5 (15)
O1—C4—C5—C6	57.4 (12)	C25—C26—C27—C28	−1.3 (17)
C3—C4—C5—C6	172.1 (9)	C26—C27—C28—C29	2.3 (19)
C17—O5—C6—C5	−168.5 (7)	C25—C24—C29—C28	−0.3 (17)
O6—C5—C6—O5	−55.3 (11)	C17—C24—C29—C28	178.9 (10)
C4—C5—C6—O5	63.5 (11)	C27—C28—C29—C24	−1.5 (19)
C1—O2—C7—O3	27.1 (13)	O5—C17—C30—C31	−80.3 (13)
C1—O2—C7—C8	143.2 (11)	C18—C17—C30—C31	154.0 (11)
C1—O2—C7—C9	−93.0 (11)	C24—C17—C30—C31	34.7 (14)
C2—O3—C7—O2	−35.1 (12)	O5—C17—C30—C35	94.1 (12)
C2—O3—C7—C8	−151.5 (12)	C18—C17—C30—C35	−31.6 (16)
C2—O3—C7—C9	82.7 (13)	C24—C17—C30—C35	−151.0 (11)
C3—O4—C10—C11	−177.7 (9)	C35—C30—C31—C32	2.3 (19)
O4—C10—C11—C16	−87.3 (13)	C17—C30—C31—C32	177.0 (12)
O4—C10—C11—C12	92.2 (13)	C30—C31—C32—C33	−1 (2)
C16—C11—C12—C13	−2 (2)	C31—C32—C33—C34	−1 (2)
C10—C11—C12—C13	178.8 (12)	C32—C33—C34—C35	0 (2)
C11—C12—C13—C14	0 (2)	C33—C34—C35—C30	1 (2)
C12—C13—C14—C15	1 (3)	C31—C30—C35—C34	−2.6 (19)
C13—C14—C15—C16	−1 (3)	C17—C30—C35—C34	−177.2 (12)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C34—H34···O8^i	0.95	2.55	3.179 (17)	124
C25—H25···Cg3^ii	0.95	2.99	3.830 (12)	149

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

\ (3aR,5S,6S,6aR)-5-[1-Azido-2-(trityloxy)ethyl]-6-\ benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (4)

Crystal data

C35H35N3O5	Dx = 1.259 Mg m^−3
Mr = 577.66	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 46634 reflections
a = 10.0943 (1) Å	θ = 4.3–76.0°
b = 10.9625 (1) Å	µ = 0.68 mm^−1
c = 27.5392 (2) Å	T = 150 K
V = 3047.45 (5) Å^3	Prismatic fragment, colourless
Z = 4	0.26 × 0.15 × 0.13 mm
F(000) = 1224

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	6389 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	6282 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.5861 pixels mm^-1	θmax = 76.5°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −13→13
Tmin = 0.676, Tmax = 1.000	l = −33→34
73112 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.2613P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.085	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.39 e Å^−3
6389 reflections	Δρmin = −0.18 e Å^−3
391 parameters	Extinction correction: (SHELXL2018; Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0007 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 2717 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (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
O1	0.18408 (10)	0.60187 (9)	0.10645 (4)	0.0270 (2)
O2	0.00591 (11)	0.70764 (11)	0.13994 (4)	0.0328 (3)
O3	−0.13375 (11)	0.56706 (10)	0.10832 (4)	0.0296 (2)
O4	0.10606 (11)	0.44527 (11)	0.02350 (4)	0.0291 (2)
O5	0.15534 (10)	0.23286 (9)	0.13663 (4)	0.0246 (2)
N1	0.35781 (13)	0.41981 (12)	0.14726 (5)	0.0300 (3)
N2	0.43200 (15)	0.50814 (14)	0.14439 (5)	0.0354 (3)
N3	0.5025 (2)	0.58666 (18)	0.14562 (9)	0.0598 (5)
C1	0.06810 (15)	0.66879 (13)	0.09676 (6)	0.0268 (3)
H1	0.086933	0.739408	0.074834	0.032*
C2	−0.03197 (15)	0.58033 (13)	0.07341 (5)	0.0261 (3)
H2	−0.065704	0.610124	0.041393	0.031*
C3	0.04319 (15)	0.45956 (13)	0.06926 (5)	0.0248 (3)
H4	−0.016245	0.388852	0.076452	0.030*
C4	0.14788 (14)	0.47460 (12)	0.10874 (5)	0.0236 (3)
H5	0.106924	0.457226	0.141073	0.028*
C5	0.27373 (14)	0.39970 (13)	0.10348 (5)	0.0246 (3)
H6	0.323017	0.427614	0.074010	0.030*
C6	0.24742 (14)	0.26381 (13)	0.09944 (5)	0.0255 (3)
H6A	0.210161	0.244124	0.067120	0.031*
H6B	0.330759	0.217442	0.103720	0.031*
C7	−0.13035 (16)	0.67123 (14)	0.13941 (6)	0.0284 (3)
C8	−0.16999 (18)	0.6312 (2)	0.18961 (6)	0.0403 (4)
H8A	−0.261046	0.600252	0.188955	0.060*
H8B	−0.164574	0.700762	0.211883	0.060*
H8C	−0.110156	0.566556	0.200704	0.060*
C9	−0.21657 (19)	0.77199 (16)	0.11883 (7)	0.0397 (4)
H9A	−0.186880	0.791990	0.085902	0.060*
H9B	−0.209628	0.844528	0.139474	0.060*
H9C	−0.308936	0.744573	0.117824	0.060*
C10	0.01360 (17)	0.42805 (18)	−0.01546 (6)	0.0383 (4)
H10A	−0.012860	0.508124	−0.028962	0.046*
H10B	−0.066870	0.386567	−0.003230	0.046*
C11	0.07737 (15)	0.35211 (16)	−0.05432 (6)	0.0302 (3)
C12	0.11051 (18)	0.23157 (16)	−0.04514 (6)	0.0354 (4)
H12	0.093305	0.197681	−0.014029	0.042*
C13	0.16831 (19)	0.15995 (16)	−0.08068 (7)	0.0382 (4)
H13	0.190812	0.077529	−0.073932	0.046*
C14	0.19326 (18)	0.20894 (18)	−0.12618 (6)	0.0374 (4)
H14	0.233078	0.159988	−0.150614	0.045*
C15	0.16047 (17)	0.32848 (18)	−0.13608 (6)	0.0370 (4)
H15	0.177332	0.361637	−0.167347	0.044*
C16	0.10255 (16)	0.40072 (16)	−0.10021 (6)	0.0338 (3)
H16	0.080218	0.483138	−0.107031	0.041*
C17	0.13412 (14)	0.10522 (12)	0.14551 (5)	0.0221 (3)
C18	0.25661 (14)	0.04939 (14)	0.17016 (5)	0.0247 (3)
C19	0.33940 (15)	0.12422 (15)	0.19749 (5)	0.0295 (3)
H19	0.323232	0.209544	0.198606	0.035*
C20	0.44561 (17)	0.07539 (18)	0.22319 (6)	0.0380 (4)
H20	0.501120	0.127678	0.241697	0.046*
C21	0.47113 (18)	−0.04860 (19)	0.22204 (7)	0.0425 (4)
H21	0.543924	−0.081546	0.239532	0.051*
C22	0.38886 (18)	−0.12450 (17)	0.19494 (7)	0.0393 (4)
H22	0.405765	−0.209706	0.193810	0.047*
C23	0.28199 (16)	−0.07606 (15)	0.16951 (6)	0.0305 (3)
H23	0.225656	−0.128736	0.151509	0.037*
C24	0.09417 (14)	0.04392 (13)	0.09745 (5)	0.0239 (3)
C25	0.18732 (16)	−0.01114 (14)	0.06702 (5)	0.0280 (3)
H25	0.277293	−0.015847	0.076968	0.034*
C26	0.14980 (18)	−0.05930 (15)	0.02220 (6)	0.0332 (3)
H26	0.214126	−0.096942	0.001967	0.040*
C27	0.0192 (2)	−0.05246 (16)	0.00708 (6)	0.0359 (4)
H27	−0.006660	−0.087082	−0.023088	0.043*
C28	−0.07333 (17)	0.00507 (18)	0.03617 (6)	0.0358 (4)
H28	−0.162552	0.011971	0.025543	0.043*
C29	−0.03610 (16)	0.05300 (15)	0.08105 (6)	0.0301 (3)
H29	−0.100456	0.092409	0.100731	0.036*
C30	0.02126 (14)	0.10232 (13)	0.18324 (5)	0.0231 (3)
C31	−0.02863 (15)	0.20958 (14)	0.20323 (5)	0.0260 (3)
H31	0.003067	0.286132	0.191984	0.031*
C32	−0.12446 (16)	0.20572 (15)	0.23951 (6)	0.0298 (3)
H32	−0.157422	0.279573	0.252919	0.036*
C33	−0.17216 (15)	0.09483 (16)	0.25623 (5)	0.0298 (3)
H33	−0.236550	0.092243	0.281369	0.036*
C34	−0.12473 (16)	−0.01243 (15)	0.23581 (6)	0.0293 (3)
H34	−0.158170	−0.088721	0.246647	0.035*
C35	−0.02869 (15)	−0.00910 (14)	0.19965 (5)	0.0272 (3)
H35	0.003151	−0.083097	0.186006	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0230 (5)	0.0237 (5)	0.0343 (5)	−0.0036 (4)	−0.0021 (4)	0.0010 (4)
O2	0.0263 (5)	0.0339 (6)	0.0380 (6)	−0.0031 (5)	−0.0022 (4)	−0.0108 (5)
O3	0.0262 (5)	0.0293 (5)	0.0332 (6)	−0.0044 (4)	0.0042 (4)	−0.0081 (4)
O4	0.0251 (5)	0.0395 (6)	0.0228 (5)	0.0016 (5)	−0.0013 (4)	−0.0039 (4)
O5	0.0245 (5)	0.0235 (5)	0.0259 (5)	0.0000 (4)	0.0055 (4)	0.0011 (4)
N1	0.0248 (6)	0.0338 (7)	0.0314 (7)	−0.0023 (5)	−0.0049 (5)	0.0024 (5)
N2	0.0290 (7)	0.0374 (7)	0.0398 (7)	−0.0013 (6)	−0.0027 (6)	−0.0040 (6)
N3	0.0427 (9)	0.0518 (10)	0.0849 (15)	−0.0151 (9)	−0.0110 (9)	−0.0058 (10)
C1	0.0260 (7)	0.0247 (6)	0.0297 (7)	−0.0020 (5)	−0.0027 (6)	0.0021 (5)
C2	0.0232 (6)	0.0294 (7)	0.0257 (7)	−0.0013 (5)	−0.0015 (5)	−0.0013 (5)
C3	0.0229 (6)	0.0273 (6)	0.0240 (7)	−0.0017 (5)	0.0002 (5)	−0.0024 (5)
C4	0.0233 (6)	0.0233 (6)	0.0242 (6)	−0.0030 (5)	0.0000 (5)	0.0006 (5)
C5	0.0227 (6)	0.0277 (7)	0.0234 (6)	−0.0022 (5)	0.0009 (5)	0.0017 (5)
C6	0.0244 (7)	0.0271 (7)	0.0250 (6)	−0.0003 (5)	0.0048 (5)	0.0016 (5)
C7	0.0255 (7)	0.0280 (7)	0.0317 (7)	−0.0006 (6)	−0.0017 (6)	−0.0057 (6)
C8	0.0345 (8)	0.0554 (10)	0.0309 (8)	0.0002 (8)	0.0004 (7)	−0.0038 (7)
C9	0.0333 (8)	0.0336 (8)	0.0522 (10)	0.0029 (7)	−0.0048 (8)	−0.0029 (7)
C10	0.0307 (8)	0.0541 (10)	0.0299 (8)	0.0096 (8)	−0.0066 (6)	−0.0103 (7)
C11	0.0233 (7)	0.0414 (8)	0.0259 (7)	0.0015 (6)	−0.0049 (5)	−0.0057 (6)
C12	0.0368 (9)	0.0410 (8)	0.0284 (7)	−0.0008 (7)	0.0012 (6)	0.0025 (6)
C13	0.0395 (9)	0.0361 (8)	0.0391 (9)	0.0010 (7)	0.0035 (7)	−0.0033 (7)
C14	0.0302 (8)	0.0480 (10)	0.0339 (8)	−0.0024 (7)	0.0030 (6)	−0.0101 (7)
C15	0.0297 (8)	0.0549 (10)	0.0263 (7)	−0.0035 (7)	0.0007 (6)	0.0039 (7)
C16	0.0277 (7)	0.0407 (8)	0.0331 (8)	−0.0002 (6)	−0.0046 (6)	0.0028 (7)
C17	0.0206 (6)	0.0234 (6)	0.0224 (6)	0.0002 (5)	0.0020 (5)	0.0003 (5)
C18	0.0209 (6)	0.0297 (7)	0.0234 (6)	0.0005 (5)	0.0024 (5)	0.0030 (5)
C19	0.0260 (7)	0.0357 (8)	0.0269 (7)	−0.0015 (6)	−0.0002 (6)	0.0018 (6)
C20	0.0276 (8)	0.0522 (10)	0.0341 (8)	−0.0047 (8)	−0.0062 (6)	0.0052 (7)
C21	0.0279 (8)	0.0562 (11)	0.0433 (9)	0.0059 (8)	−0.0048 (7)	0.0146 (8)
C22	0.0319 (8)	0.0381 (8)	0.0479 (10)	0.0069 (7)	0.0017 (7)	0.0129 (7)
C23	0.0267 (7)	0.0297 (7)	0.0350 (8)	0.0015 (6)	0.0015 (6)	0.0060 (6)
C24	0.0252 (7)	0.0249 (6)	0.0217 (6)	−0.0014 (5)	0.0024 (5)	0.0017 (5)
C25	0.0287 (7)	0.0283 (7)	0.0271 (7)	0.0005 (6)	0.0045 (6)	0.0011 (6)
C26	0.0417 (9)	0.0307 (7)	0.0271 (7)	0.0005 (7)	0.0084 (6)	0.0004 (6)
C27	0.0473 (10)	0.0375 (8)	0.0230 (7)	−0.0076 (7)	−0.0001 (6)	−0.0003 (6)
C28	0.0323 (8)	0.0484 (9)	0.0268 (7)	−0.0053 (7)	−0.0027 (6)	0.0015 (7)
C29	0.0262 (7)	0.0394 (8)	0.0248 (7)	0.0007 (6)	0.0007 (6)	0.0002 (6)
C30	0.0203 (6)	0.0287 (7)	0.0201 (6)	−0.0011 (5)	−0.0008 (5)	0.0003 (5)
C31	0.0253 (7)	0.0284 (7)	0.0243 (6)	−0.0007 (6)	0.0004 (6)	−0.0022 (5)
C32	0.0287 (7)	0.0357 (8)	0.0249 (7)	0.0022 (6)	0.0016 (6)	−0.0065 (6)
C33	0.0248 (7)	0.0444 (8)	0.0201 (6)	−0.0009 (6)	0.0015 (5)	0.0004 (6)
C34	0.0257 (7)	0.0353 (7)	0.0269 (7)	−0.0044 (6)	0.0013 (6)	0.0048 (6)
C35	0.0251 (7)	0.0287 (7)	0.0277 (7)	−0.0013 (6)	0.0022 (6)	0.0008 (6)

Geometric parameters (Å, º)

O1—C1	1.4071 (18)	C14—C15	1.379 (3)
O1—C4	1.4437 (16)	C14—H14	0.9500
O2—C1	1.4106 (19)	C15—C16	1.395 (2)
O2—C7	1.4323 (19)	C15—H15	0.9500
O3—C2	1.4146 (18)	C16—H16	0.9500
O3—C7	1.4276 (17)	C17—C24	1.5383 (19)
O4—C3	1.4197 (17)	C17—C18	1.5376 (19)
O4—C10	1.4346 (19)	C17—C30	1.5422 (19)
O5—C6	1.4241 (17)	C18—C19	1.392 (2)
O5—C17	1.4365 (17)	C18—C23	1.399 (2)
N1—N2	1.227 (2)	C19—C20	1.392 (2)
N1—C5	1.4907 (18)	C19—H19	0.9500
N2—N3	1.118 (2)	C20—C21	1.384 (3)
C1—C2	1.541 (2)	C20—H20	0.9500
C1—H1	1.0000	C21—C22	1.392 (3)
C2—C3	1.530 (2)	C21—H21	0.9500
C2—H2	1.0000	C22—C23	1.392 (2)
C3—C4	1.5251 (19)	C22—H22	0.9500
C3—H4	1.0000	C23—H23	0.9500
C4—C5	1.519 (2)	C24—C29	1.394 (2)
C4—H5	1.0000	C24—C25	1.397 (2)
C5—C6	1.517 (2)	C25—C26	1.395 (2)
C5—H6	1.0000	C25—H25	0.9500
C6—H6A	0.9900	C26—C27	1.384 (3)
C6—H6B	0.9900	C26—H26	0.9500
C7—C8	1.505 (2)	C27—C28	1.383 (3)
C7—C9	1.516 (2)	C27—H27	0.9500
C8—H8A	0.9800	C28—C29	1.395 (2)
C8—H8B	0.9800	C28—H28	0.9500
C8—H8C	0.9800	C29—H29	0.9500
C9—H9A	0.9800	C30—C31	1.393 (2)
C9—H9B	0.9800	C30—C35	1.396 (2)
C9—H9C	0.9800	C31—C32	1.391 (2)
C10—C11	1.501 (2)	C31—H31	0.9500
C10—H10A	0.9900	C32—C33	1.386 (2)
C10—H10B	0.9900	C32—H32	0.9500
C11—C12	1.386 (2)	C33—C34	1.388 (2)
C11—C16	1.395 (2)	C33—H33	0.9500
C12—C13	1.384 (2)	C34—C35	1.390 (2)
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.386 (3)	C35—H35	0.9500
C13—H13	0.9500
C1—O1—C4	107.55 (10)	C12—C13—C14	119.74 (17)
C1—O2—C7	109.54 (11)	C12—C13—H13	120.1
C2—O3—C7	107.93 (11)	C14—C13—H13	120.1
C3—O4—C10	112.81 (12)	C15—C14—C13	120.23 (17)
C6—O5—C17	116.87 (11)	C15—C14—H14	119.9
N2—N1—C5	114.34 (13)	C13—C14—H14	119.9
N3—N2—N1	174.2 (2)	C14—C15—C16	120.01 (16)
O1—C1—O2	111.58 (12)	C14—C15—H15	120.0
O1—C1—C2	107.25 (11)	C16—C15—H15	120.0
O2—C1—C2	104.48 (12)	C15—C16—C11	120.08 (16)
O1—C1—H1	111.1	C15—C16—H16	120.0
O2—C1—H1	111.1	C11—C16—H16	120.0
C2—C1—H1	111.1	O5—C17—C24	108.54 (11)
O3—C2—C3	108.77 (12)	O5—C17—C18	110.07 (11)
O3—C2—C1	104.90 (11)	C24—C17—C18	114.63 (12)
C3—C2—C1	104.51 (12)	O5—C17—C30	104.18 (11)
O3—C2—H2	112.7	C24—C17—C30	112.15 (11)
C3—C2—H2	112.7	C18—C17—C30	106.76 (11)
C1—C2—H2	112.7	C19—C18—C23	118.44 (14)
O4—C3—C4	109.57 (12)	C19—C18—C17	119.13 (13)
O4—C3—C2	112.54 (12)	C23—C18—C17	122.20 (13)
C4—C3—C2	101.35 (11)	C18—C19—C20	120.71 (16)
O4—C3—H4	111.0	C18—C19—H19	119.6
C4—C3—H4	111.0	C20—C19—H19	119.6
C2—C3—H4	111.0	C21—C20—C19	120.64 (17)
O1—C4—C5	107.85 (11)	C21—C20—H20	119.7
O1—C4—C3	104.40 (11)	C19—C20—H20	119.7
C5—C4—C3	116.94 (12)	C20—C21—C22	119.22 (17)
O1—C4—H5	109.1	C20—C21—H21	120.4
C5—C4—H5	109.1	C22—C21—H21	120.4
C3—C4—H5	109.1	C23—C22—C21	120.27 (17)
N1—C5—C4	108.60 (12)	C23—C22—H22	119.9
N1—C5—C6	107.72 (12)	C21—C22—H22	119.9
C4—C5—C6	113.03 (12)	C22—C23—C18	120.71 (16)
N1—C5—H6	109.1	C22—C23—H23	119.6
C4—C5—H6	109.1	C18—C23—H23	119.6
C6—C5—H6	109.1	C29—C24—C25	118.14 (14)
O5—C6—C5	107.18 (12)	C29—C24—C17	119.66 (13)
O5—C6—H6A	110.3	C25—C24—C17	121.91 (13)
C5—C6—H6A	110.3	C24—C25—C26	120.77 (15)
O5—C6—H6B	110.3	C24—C25—H25	119.6
C5—C6—H6B	110.3	C26—C25—H25	119.6
H6A—C6—H6B	108.5	C27—C26—C25	120.28 (15)
O3—C7—O2	104.61 (12)	C27—C26—H26	119.9
O3—C7—C8	108.15 (13)	C25—C26—H26	119.9
O2—C7—C8	109.10 (13)	C28—C27—C26	119.58 (15)
O3—C7—C9	110.17 (13)	C28—C27—H27	120.2
O2—C7—C9	110.61 (13)	C26—C27—H27	120.2
C8—C7—C9	113.78 (15)	C27—C28—C29	120.21 (16)
C7—C8—H8A	109.5	C27—C28—H28	119.9
C7—C8—H8B	109.5	C29—C28—H28	119.9
H8A—C8—H8B	109.5	C28—C29—C24	120.96 (15)
C7—C8—H8C	109.5	C28—C29—H29	119.5
H8A—C8—H8C	109.5	C24—C29—H29	119.5
H8B—C8—H8C	109.5	C31—C30—C35	118.69 (13)
C7—C9—H9A	109.5	C31—C30—C17	121.06 (13)
C7—C9—H9B	109.5	C35—C30—C17	120.18 (13)
H9A—C9—H9B	109.5	C32—C31—C30	120.64 (14)
C7—C9—H9C	109.5	C32—C31—H31	119.7
H9A—C9—H9C	109.5	C30—C31—H31	119.7
H9B—C9—H9C	109.5	C33—C32—C31	120.44 (14)
O4—C10—C11	109.10 (13)	C33—C32—H32	119.8
O4—C10—H10A	109.9	C31—C32—H32	119.8
C11—C10—H10A	109.9	C32—C33—C34	119.23 (14)
O4—C10—H10B	109.9	C32—C33—H33	120.4
C11—C10—H10B	109.9	C34—C33—H33	120.4
H10A—C10—H10B	108.3	C35—C34—C33	120.55 (15)
C12—C11—C16	119.04 (15)	C35—C34—H34	119.7
C12—C11—C10	120.14 (15)	C33—C34—H34	119.7
C16—C11—C10	120.81 (16)	C34—C35—C30	120.43 (15)
C13—C12—C11	120.90 (16)	C34—C35—H35	119.8
C13—C12—H12	119.5	C30—C35—H35	119.8
C11—C12—H12	119.5
C4—O1—C1—O2	92.03 (13)	C10—C11—C16—C15	−179.25 (15)
C4—O1—C1—C2	−21.82 (15)	C6—O5—C17—C24	−54.81 (15)
C7—O2—C1—O1	−127.43 (12)	C6—O5—C17—C18	71.38 (15)
C7—O2—C1—C2	−11.87 (15)	C6—O5—C17—C30	−174.48 (11)
C7—O3—C2—C3	134.00 (12)	O5—C17—C18—C19	25.84 (17)
C7—O3—C2—C1	22.64 (15)	C24—C17—C18—C19	148.52 (13)
O1—C1—C2—O3	111.98 (13)	C30—C17—C18—C19	−86.65 (15)
O2—C1—C2—O3	−6.57 (15)	O5—C17—C18—C23	−159.64 (13)
O1—C1—C2—C3	−2.41 (15)	C24—C17—C18—C23	−36.96 (19)
O2—C1—C2—C3	−120.95 (12)	C30—C17—C18—C23	87.87 (16)
C10—O4—C3—C4	178.79 (13)	C23—C18—C19—C20	0.6 (2)
C10—O4—C3—C2	−69.26 (16)	C17—C18—C19—C20	175.29 (14)
O3—C2—C3—O4	155.11 (12)	C18—C19—C20—C21	0.1 (3)
C1—C2—C3—O4	−93.26 (14)	C19—C20—C21—C22	−0.2 (3)
O3—C2—C3—C4	−87.93 (13)	C20—C21—C22—C23	−0.3 (3)
C1—C2—C3—C4	23.70 (14)	C21—C22—C23—C18	0.9 (3)
C1—O1—C4—C5	162.76 (12)	C19—C18—C23—C22	−1.1 (2)
C1—O1—C4—C3	37.73 (14)	C17—C18—C23—C22	−175.62 (14)
O4—C3—C4—O1	81.90 (13)	O5—C17—C24—C29	−80.11 (16)
C2—C3—C4—O1	−37.20 (13)	C18—C17—C24—C29	156.39 (13)
O4—C3—C4—C5	−37.14 (16)	C30—C17—C24—C29	34.45 (18)
C2—C3—C4—C5	−156.24 (12)	O5—C17—C24—C25	93.58 (15)
N2—N1—C5—C4	−87.25 (16)	C18—C17—C24—C25	−29.91 (19)
N2—N1—C5—C6	150.02 (14)	C30—C17—C24—C25	−151.86 (13)
O1—C4—C5—N1	67.21 (14)	C29—C24—C25—C26	−2.1 (2)
C3—C4—C5—N1	−175.62 (12)	C17—C24—C25—C26	−175.92 (13)
O1—C4—C5—C6	−173.32 (11)	C24—C25—C26—C27	0.4 (2)
C3—C4—C5—C6	−56.15 (16)	C25—C26—C27—C28	1.6 (3)
C17—O5—C6—C5	−168.94 (11)	C26—C27—C28—C29	−1.7 (3)
N1—C5—C6—O5	73.10 (14)	C27—C28—C29—C24	−0.1 (3)
C4—C5—C6—O5	−46.88 (16)	C25—C24—C29—C28	2.0 (2)
C2—O3—C7—O2	−30.07 (16)	C17—C24—C29—C28	175.90 (14)
C2—O3—C7—C8	−146.25 (13)	O5—C17—C30—C31	−4.74 (17)
C2—O3—C7—C9	88.83 (15)	C24—C17—C30—C31	−121.94 (14)
C1—O2—C7—O3	25.84 (16)	C18—C17—C30—C31	111.73 (15)
C1—O2—C7—C8	141.36 (14)	O5—C17—C30—C35	178.22 (12)
C1—O2—C7—C9	−92.76 (15)	C24—C17—C30—C35	61.02 (17)
C3—O4—C10—C11	−150.62 (14)	C18—C17—C30—C35	−65.31 (16)
O4—C10—C11—C12	66.0 (2)	C35—C30—C31—C32	1.3 (2)
O4—C10—C11—C16	−114.86 (17)	C17—C30—C31—C32	−175.82 (13)
C16—C11—C12—C13	0.3 (3)	C30—C31—C32—C33	−0.2 (2)
C10—C11—C12—C13	179.44 (16)	C31—C32—C33—C34	−1.0 (2)
C11—C12—C13—C14	−0.2 (3)	C32—C33—C34—C35	1.2 (2)
C12—C13—C14—C15	−0.1 (3)	C33—C34—C35—C30	−0.2 (2)
C13—C14—C15—C16	0.3 (3)	C31—C30—C35—C34	−1.1 (2)
C14—C15—C16—C11	−0.2 (3)	C17—C30—C35—C34	176.04 (13)
C12—C11—C16—C15	−0.1 (2)

Hydrogen-bond geometry (Å, º)

Cg5 and Cg6 are the centroids of the C24–C29 and C30–C35 rings.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3^i	0.95	2.56	3.281 (2)	133
C1—H1···Cg5^ii	1.00	2.90	3.8014 (16)	150
C8—H8C···Cg6^iii	0.98	2.91	3.5435 (18)	123
C12—H12···Cg5	0.95	2.88	3.7503 (18)	153
C15—H15···Cg6^i	0.95	2.91	3.6050 (18)	131

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