2-Hydro­xy-N-(2,3,4,6-tetra-O-pivaloyl-β-D-gluco­pyran­osyl)­benzyl­idene­amine

The title compound C₃₃H₄₉NO₁₀, which is an important chiral template for the synthesis of chiral amino compounds, has been successfully synthesized. The gluco­pyran­ose ring adopts a chair conformation. There is an intramolecular O—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.047
• wR factor = 0.110
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.60 Ratio
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.78 Ratio
PLAT242_ALERT_2_A Check Low    U(eq) as Compared to Neighbors  for        C19

Alert level B
PLAT024_ALERT_4_B Merging of Friedel pairs is STRONGLY indicated .          !
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C14
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C24
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C30

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C12
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C29
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.30 Deg.
              C16A -C14  -C16B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.50 Deg.
              C17A -C14  -C17B    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               7140
           Count of symmetry unique reflns         4036
           Completeness (_total/calc)            176.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3104
           Fraction of Friedel pairs measured     0.769
           Are heavy atom types Z>Si present           no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).

(I)

Crystal data

C33H49NO10	F(000) = 1336
Mr = 619.73	Dx = 1.126 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2270 reflections
a = 11.1774 (8) Å	θ = 4.6–37.1°
b = 11.2461 (8) Å	µ = 0.08 mm^−1
c = 29.072 (2) Å	T = 293 K
V = 3654.4 (4) Å^3	Plate, yellow
Z = 4	0.37 × 0.27 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4140 independent reflections
Radiation source: fine-focus sealed tube	3502 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
Tmin = 0.907, Tmax = 0.980	k = −12→13
20250 measured reflections	l = −35→34

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0457P)^2] where P = (Fo^2 + 2Fc^2)/3
4035 reflections	(Δ/σ)max = 0.004
440 parameters	Δρmax = 0.13 e Å^−3
30 restraints	Δρmin = −0.11 e Å^−3

Special details

Experimental. Melting points were determined on a X4-Data microscopic melting point apparatus. The ¹H NMR spectrum of (I) was recorded on a DMX 500 MHz AVANCE spectrometer in CDCl₃, using TMS as internal standard.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4846 (2)	0.0678 (2)	0.32925 (8)	0.0567 (7)
O2	0.3427 (3)	−0.1287 (2)	0.20659 (11)	0.0958 (11)
H2	0.3647	−0.1003	0.2311	0.144*
O3	0.6675 (4)	−0.1519 (3)	0.21913 (10)	0.1080 (12)
O4	0.7043 (2)	0.0363 (2)	0.23790 (7)	0.0552 (6)
O5	0.9588 (3)	0.1548 (3)	0.31350 (13)	0.1116 (12)
O6	0.8424 (2)	−0.0061 (2)	0.31857 (8)	0.0569 (6)
O7	0.7974 (3)	−0.0458 (3)	0.43464 (9)	0.0868 (10)
O8	0.7512 (2)	0.1222 (2)	0.39812 (7)	0.0565 (6)
O9	0.5289 (4)	0.0423 (3)	0.49335 (11)	0.1243 (14)
O10	0.4772 (3)	−0.0058 (3)	0.42283 (9)	0.0743 (8)
N1	0.4509 (3)	0.0380 (3)	0.25172 (9)	0.0545 (8)
C1	0.5344 (3)	0.0859 (3)	0.28507 (11)	0.0501 (9)
H1	0.5477	0.1709	0.2795	0.060*
C2	0.6517 (3)	0.0185 (3)	0.28260 (11)	0.0488 (9)
H2A	0.6376	−0.0664	0.2879	0.059*
C3	0.7378 (3)	0.0666 (3)	0.31836 (11)	0.0484 (9)
H3	0.7590	0.1491	0.3112	0.058*
C4	0.6781 (3)	0.0599 (3)	0.36517 (10)	0.0490 (9)
H4	0.6685	−0.0233	0.3745	0.059*
C5	0.5569 (3)	0.1214 (3)	0.36397 (11)	0.0529 (9)
H5	0.5693	0.2051	0.3559	0.064*
C6	0.4056 (3)	0.1110 (3)	0.22367 (11)	0.0513 (9)
H6	0.4252	0.1910	0.2266	0.062*
C7	0.3249 (3)	0.0762 (3)	0.18736 (12)	0.0529 (9)
C8	0.2753 (4)	0.1603 (4)	0.15818 (14)	0.0763 (13)
H8	0.2931	0.2402	0.1627	0.092*
C9	0.2016 (4)	0.1290 (4)	0.12308 (15)	0.0856 (14)
H9	0.1685	0.1869	0.1041	0.103*
C10	0.1764 (4)	0.0117 (5)	0.11587 (15)	0.0891 (14)
H10	0.1276	−0.0103	0.0914	0.107*
C11	0.2221 (4)	−0.0734 (4)	0.14411 (16)	0.0892 (15)
H11	0.2024	−0.1529	0.1395	0.107*
C12	0.2979 (3)	−0.0418 (3)	0.17969 (13)	0.0626 (10)
C13	0.7044 (4)	−0.0566 (4)	0.20851 (13)	0.0655 (11)
C14	0.7501 (4)	−0.0249 (4)	0.16182 (14)	0.0775 (13)
C15A	0.6330 (12)	0.0043 (19)	0.1359 (5)	0.142 (7)	0.48
H15A	0.5788	−0.0615	0.1384	0.213*	0.48
H15B	0.6506	0.0186	0.1040	0.213*	0.48
H15C	0.5971	0.0739	0.1490	0.213*	0.48
C16A	0.8075 (14)	−0.1315 (13)	0.1406 (5)	0.109 (5)	0.48
H16A	0.8744	−0.1560	0.1590	0.164*	0.48
H16B	0.8347	−0.1120	0.1102	0.164*	0.48
H16C	0.7504	−0.1951	0.1388	0.164*	0.48
C17A	0.8340 (17)	0.0785 (13)	0.1632 (6)	0.135 (7)	0.48
H17A	0.7989	0.1417	0.1808	0.203*	0.48
H17B	0.8491	0.1057	0.1324	0.203*	0.48
H17C	0.9080	0.0546	0.1772	0.203*	0.48
C15B	0.6919 (13)	0.0900 (12)	0.1438 (5)	0.119 (5)	0.52
H15D	0.6066	0.0806	0.1432	0.179*	0.52
H15E	0.7203	0.1061	0.1133	0.179*	0.52
H15F	0.7126	0.1550	0.1637	0.179*	0.52
C16B	0.7279 (18)	−0.1255 (13)	0.1279 (5)	0.160 (9)	0.52
H16D	0.7542	−0.1993	0.1411	0.240*	0.52
H16E	0.7716	−0.1105	0.1000	0.240*	0.52
H16F	0.6440	−0.1302	0.1211	0.240*	0.52
C17B	0.8848 (10)	−0.0022 (18)	0.1652 (5)	0.140 (7)	0.52
H17D	0.8998	0.0571	0.1883	0.209*	0.52
H17E	0.9143	0.0251	0.1361	0.209*	0.52
H17F	0.9248	−0.0747	0.1735	0.209*	0.52
C18	0.9505 (4)	0.0485 (5)	0.31527 (14)	0.0700 (11)
C19	1.0512 (4)	−0.0380 (5)	0.31326 (17)	0.0856 (14)
C20	1.0364 (6)	−0.1213 (8)	0.2739 (2)	0.204 (4)
H20A	1.0240	−0.0767	0.2461	0.305*
H20B	0.9686	−0.1718	0.2793	0.305*
H20C	1.1071	−0.1692	0.2708	0.305*
C21	1.1669 (5)	0.0297 (7)	0.3109 (3)	0.223 (5)
H21A	1.1687	0.0763	0.2832	0.335*
H21B	1.2327	−0.0251	0.3108	0.335*
H21C	1.1732	0.0813	0.3371	0.335*
C22	1.0508 (6)	−0.1108 (6)	0.3578 (2)	0.156 (3)
H22A	1.1098	−0.1725	0.3558	0.234*
H22B	0.9732	−0.1456	0.3622	0.234*
H22C	1.0690	−0.0597	0.3833	0.234*
C23	0.8044 (4)	0.0596 (4)	0.43162 (12)	0.0597 (10)
C24	0.8742 (4)	0.1404 (4)	0.46397 (13)	0.0696 (12)
C25	0.9729 (4)	0.2022 (4)	0.43760 (15)	0.0987 (16)
H25A	1.0099	0.2608	0.4569	0.148*
H25B	0.9398	0.2401	0.4109	0.148*
H25C	1.0316	0.1448	0.4283	0.148*
C26	0.9262 (6)	0.0665 (5)	0.50238 (18)	0.147 (3)
H26A	0.9660	0.1176	0.5240	0.220*
H26B	0.9825	0.0107	0.4899	0.220*
H26C	0.8631	0.0243	0.5177	0.220*
C27	0.7915 (5)	0.2352 (5)	0.48322 (17)	0.1148 (19)
H27A	0.7288	0.1981	0.5007	0.172*
H27B	0.7572	0.2799	0.4584	0.172*
H27C	0.8362	0.2877	0.5028	0.172*
C28	0.4889 (4)	0.1160 (4)	0.40845 (13)	0.0712 (12)
H28A	0.5309	0.1610	0.4319	0.085*
H28B	0.4102	0.1509	0.4044	0.085*
C29	0.4983 (4)	−0.0329 (4)	0.46641 (15)	0.0743 (12)
C30	0.4775 (5)	−0.1612 (4)	0.47734 (15)	0.0846 (14)
C31	0.5356 (6)	−0.1893 (5)	0.52390 (16)	0.120 (2)
H31A	0.4988	−0.1420	0.5475	0.180*
H31B	0.6195	−0.1715	0.5225	0.180*
H31C	0.5250	−0.2721	0.5309	0.180*
C32	0.3462 (5)	−0.1829 (6)	0.4802 (2)	0.153 (3)
H32A	0.3099	−0.1228	0.4990	0.229*
H32B	0.3320	−0.2597	0.4936	0.229*
H32C	0.3122	−0.1803	0.4499	0.229*
C33	0.5359 (6)	−0.2380 (4)	0.44016 (17)	0.121 (2)
H33A	0.5249	−0.3205	0.4475	0.181*
H33B	0.6198	−0.2205	0.4387	0.181*
H33C	0.4995	−0.2212	0.4110	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0484 (13)	0.0701 (17)	0.0516 (15)	−0.0021 (13)	−0.0020 (12)	−0.0026 (12)
O2	0.124 (3)	0.0521 (17)	0.112 (3)	0.0019 (18)	−0.062 (2)	−0.0017 (17)
O3	0.180 (4)	0.056 (2)	0.088 (2)	−0.018 (2)	0.049 (2)	−0.0181 (16)
O4	0.0707 (16)	0.0509 (15)	0.0441 (14)	−0.0113 (14)	0.0070 (12)	−0.0011 (12)
O5	0.067 (2)	0.083 (2)	0.185 (4)	−0.0129 (19)	0.010 (2)	0.020 (3)
O6	0.0461 (13)	0.0582 (16)	0.0665 (16)	−0.0006 (14)	0.0006 (12)	−0.0029 (12)
O7	0.113 (3)	0.063 (2)	0.084 (2)	−0.0072 (19)	−0.0350 (18)	0.0124 (16)
O8	0.0722 (16)	0.0532 (15)	0.0443 (14)	−0.0109 (14)	−0.0141 (12)	−0.0011 (12)
O9	0.202 (4)	0.095 (3)	0.076 (2)	0.012 (3)	−0.014 (3)	−0.011 (2)
O10	0.0891 (19)	0.077 (2)	0.0567 (17)	−0.0101 (18)	0.0075 (15)	−0.0013 (15)
N1	0.0629 (19)	0.0501 (19)	0.0505 (18)	−0.0018 (17)	−0.0106 (16)	−0.0016 (15)
C1	0.056 (2)	0.045 (2)	0.050 (2)	−0.0066 (19)	−0.0052 (18)	−0.0012 (16)
C2	0.055 (2)	0.046 (2)	0.045 (2)	−0.0049 (19)	−0.0025 (17)	−0.0009 (16)
C3	0.047 (2)	0.049 (2)	0.050 (2)	−0.0040 (18)	−0.0007 (17)	0.0008 (17)
C4	0.054 (2)	0.051 (2)	0.043 (2)	−0.006 (2)	−0.0002 (17)	−0.0061 (16)
C5	0.057 (2)	0.054 (2)	0.049 (2)	−0.003 (2)	0.0028 (18)	−0.0074 (18)
C6	0.059 (2)	0.043 (2)	0.052 (2)	−0.001 (2)	−0.0016 (19)	−0.0051 (18)
C7	0.051 (2)	0.055 (2)	0.053 (2)	0.0049 (19)	−0.0068 (18)	−0.0075 (18)
C8	0.105 (4)	0.051 (2)	0.073 (3)	0.004 (3)	−0.032 (3)	0.004 (2)
C9	0.104 (4)	0.072 (3)	0.082 (3)	0.008 (3)	−0.042 (3)	0.001 (2)
C10	0.102 (3)	0.081 (3)	0.084 (3)	0.015 (3)	−0.044 (3)	−0.017 (3)
C11	0.107 (4)	0.059 (3)	0.102 (4)	0.004 (3)	−0.052 (3)	−0.018 (3)
C12	0.069 (2)	0.051 (2)	0.068 (3)	0.015 (2)	−0.022 (2)	−0.002 (2)
C13	0.087 (3)	0.055 (3)	0.055 (2)	−0.007 (3)	0.008 (2)	−0.004 (2)
C14	0.090 (3)	0.092 (4)	0.050 (2)	−0.004 (3)	0.007 (2)	−0.011 (2)
C15A	0.125 (13)	0.23 (2)	0.072 (8)	0.051 (14)	0.005 (9)	0.043 (13)
C16A	0.125 (12)	0.139 (12)	0.064 (10)	0.012 (11)	0.035 (8)	−0.019 (8)
C17A	0.20 (2)	0.120 (13)	0.084 (9)	−0.067 (13)	0.048 (13)	−0.004 (9)
C15B	0.118 (12)	0.141 (13)	0.099 (10)	0.008 (9)	0.009 (8)	0.061 (9)
C16B	0.28 (3)	0.123 (12)	0.083 (10)	−0.029 (17)	0.008 (15)	−0.052 (9)
C17B	0.096 (8)	0.24 (2)	0.085 (9)	−0.002 (13)	0.035 (7)	0.034 (15)
C18	0.057 (3)	0.081 (3)	0.072 (3)	−0.002 (3)	0.005 (2)	0.005 (3)
C19	0.058 (3)	0.106 (4)	0.093 (4)	0.013 (3)	0.008 (3)	−0.011 (3)
C20	0.163 (6)	0.273 (9)	0.175 (7)	0.124 (7)	−0.040 (5)	−0.135 (7)
C21	0.062 (4)	0.179 (7)	0.430 (14)	−0.005 (5)	0.065 (6)	−0.007 (8)
C22	0.141 (5)	0.182 (7)	0.145 (6)	0.085 (5)	0.005 (5)	0.034 (5)
C23	0.069 (3)	0.061 (3)	0.049 (2)	−0.003 (2)	−0.005 (2)	0.002 (2)
C24	0.084 (3)	0.074 (3)	0.051 (2)	−0.018 (3)	−0.014 (2)	0.000 (2)
C25	0.090 (3)	0.110 (4)	0.096 (4)	−0.018 (3)	−0.017 (3)	−0.016 (3)
C26	0.213 (7)	0.135 (5)	0.091 (4)	−0.018 (5)	−0.085 (4)	0.020 (4)
C27	0.113 (4)	0.125 (4)	0.106 (4)	−0.019 (4)	0.011 (3)	−0.064 (3)
C28	0.077 (3)	0.076 (3)	0.061 (3)	0.004 (3)	0.011 (2)	−0.010 (2)
C29	0.086 (3)	0.083 (4)	0.054 (3)	0.011 (3)	0.017 (2)	−0.009 (2)
C30	0.095 (4)	0.080 (3)	0.079 (3)	−0.010 (3)	0.030 (3)	0.001 (3)
C31	0.143 (5)	0.128 (5)	0.090 (4)	0.023 (4)	0.013 (4)	0.021 (3)
C32	0.088 (4)	0.160 (6)	0.210 (7)	−0.036 (4)	0.019 (4)	0.057 (5)
C33	0.178 (6)	0.077 (3)	0.107 (4)	−0.018 (4)	0.045 (4)	−0.021 (3)

Geometric parameters (Å, º)

O1—C1	1.415 (4)	C17A—H17A	0.9600
O1—C5	1.427 (4)	C17A—H17B	0.9600
O2—C12	1.348 (4)	C17A—H17C	0.9600
O2—H2	0.8200	C15B—H15D	0.9600
O3—C13	1.189 (4)	C15B—H15E	0.9600
O4—C13	1.350 (4)	C15B—H15F	0.9600
O4—C2	1.440 (4)	C16B—H16D	0.9600
O5—C18	1.200 (5)	C16B—H16E	0.9600
O6—C18	1.358 (5)	C16B—H16F	0.9600
O6—C3	1.427 (4)	C17B—H17D	0.9600
O7—C23	1.191 (4)	C17B—H17E	0.9600
O8—C23	1.341 (4)	C17B—H17F	0.9600
O8—C4	1.441 (4)	C18—C19	1.489 (6)
O9—C29	1.202 (5)	C19—C20	1.488 (7)
O10—C29	1.324 (5)	C19—C21	1.502 (7)
O10—C28	1.438 (5)	C19—C22	1.532 (7)
N1—C6	1.263 (4)	C20—H20A	0.9600
N1—C1	1.450 (4)	C20—H20B	0.9600
C1—C2	1.515 (5)	C20—H20C	0.9600
C1—H1	0.9800	C21—H21A	0.9600
C2—C3	1.517 (4)	C21—H21B	0.9600
C2—H2A	0.9800	C21—H21C	0.9600
C3—C4	1.518 (4)	C22—H22A	0.9600
C3—H3	0.9800	C22—H22B	0.9600
C4—C5	1.521 (5)	C22—H22C	0.9600
C4—H4	0.9800	C23—C24	1.523 (5)
C5—C28	1.501 (4)	C24—C26	1.508 (6)
C5—H5	0.9800	C24—C25	1.512 (6)
C6—C7	1.443 (4)	C24—C27	1.519 (6)
C6—H6	0.9300	C25—H25A	0.9600
C7—C12	1.380 (5)	C25—H25B	0.9600
C7—C8	1.386 (5)	C25—H25C	0.9600
C8—C9	1.358 (5)	C26—H26A	0.9600
C8—H8	0.9300	C26—H26B	0.9600
C9—C10	1.365 (6)	C26—H26C	0.9600
C9—H9	0.9300	C27—H27A	0.9600
C10—C11	1.360 (6)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600
C11—C12	1.383 (5)	C28—H28A	0.9700
C11—H11	0.9300	C28—H28B	0.9700
C13—C14	1.493 (5)	C29—C30	1.496 (6)
C14—C16A	1.494 (12)	C30—C32	1.490 (7)
C14—C17A	1.495 (13)	C30—C33	1.530 (6)
C14—C16B	1.521 (11)	C30—C31	1.534 (6)
C14—C17B	1.531 (12)	C31—H31A	0.9600
C14—C15B	1.539 (12)	C31—H31B	0.9600
C14—C15A	1.546 (12)	C31—H31C	0.9600
C15A—H15A	0.9600	C32—H32A	0.9600
C15A—H15B	0.9600	C32—H32B	0.9600
C15A—H15C	0.9600	C32—H32C	0.9600
C16A—H16A	0.9600	C33—H33A	0.9600
C16A—H16B	0.9600	C33—H33B	0.9600
C16A—H16C	0.9600	C33—H33C	0.9600
C1—O1—C5	111.0 (2)	C14—C16B—H16E	109.5
C12—O2—H2	109.5	H16D—C16B—H16E	109.5
C13—O4—C2	117.6 (3)	C14—C16B—H16F	109.5
C18—O6—C3	118.0 (3)	H16D—C16B—H16F	109.5
C23—O8—C4	118.6 (3)	H16E—C16B—H16F	109.5
C29—O10—C28	118.7 (3)	C14—C17B—H17D	109.5
C6—N1—C1	116.6 (3)	C14—C17B—H17E	109.5
O1—C1—N1	107.4 (3)	H17D—C17B—H17E	109.5
O1—C1—C2	108.2 (3)	C14—C17B—H17F	109.5
N1—C1—C2	109.8 (3)	H17D—C17B—H17F	109.5
O1—C1—H1	110.4	H17E—C17B—H17F	109.5
N1—C1—H1	110.4	O5—C18—O6	121.5 (4)
C2—C1—H1	110.4	O5—C18—C19	126.2 (4)
O4—C2—C1	109.1 (3)	O6—C18—C19	112.3 (4)
O4—C2—C3	108.0 (3)	C20—C19—C18	110.9 (4)
C1—C2—C3	109.7 (3)	C20—C19—C21	112.3 (5)
O4—C2—H2A	110.0	C18—C19—C21	108.7 (5)
C1—C2—H2A	110.0	C20—C19—C22	108.3 (6)
C3—C2—H2A	110.0	C18—C19—C22	108.3 (4)
O6—C3—C2	108.6 (3)	C21—C19—C22	108.2 (5)
O6—C3—C4	109.1 (3)	C19—C20—H20A	109.5
C2—C3—C4	108.5 (3)	C19—C20—H20B	109.5
O6—C3—H3	110.2	H20A—C20—H20B	109.5
C2—C3—H3	110.2	C19—C20—H20C	109.5
C4—C3—H3	110.2	H20A—C20—H20C	109.5
O8—C4—C3	108.8 (3)	H20B—C20—H20C	109.5
O8—C4—C5	107.4 (3)	C19—C21—H21A	109.5
C3—C4—C5	110.4 (3)	C19—C21—H21B	109.5
O8—C4—H4	110.1	H21A—C21—H21B	109.5
C3—C4—H4	110.1	C19—C21—H21C	109.5
C5—C4—H4	110.1	H21A—C21—H21C	109.5
O1—C5—C28	107.8 (3)	H21B—C21—H21C	109.5
O1—C5—C4	109.2 (3)	C19—C22—H22A	109.5
C28—C5—C4	114.4 (3)	C19—C22—H22B	109.5
O1—C5—H5	108.5	H22A—C22—H22B	109.5
C28—C5—H5	108.5	C19—C22—H22C	109.5
C4—C5—H5	108.5	H22A—C22—H22C	109.5
N1—C6—C7	123.1 (3)	H22B—C22—H22C	109.5
N1—C6—H6	118.4	O7—C23—O8	123.2 (4)
C7—C6—H6	118.4	O7—C23—C24	125.6 (4)
C12—C7—C8	118.1 (3)	O8—C23—C24	111.3 (3)
C12—C7—C6	121.1 (3)	C26—C24—C25	110.4 (4)
C8—C7—C6	120.9 (3)	C26—C24—C27	110.4 (4)
C9—C8—C7	121.7 (4)	C25—C24—C27	107.9 (4)
C9—C8—H8	119.2	C26—C24—C23	109.1 (4)
C7—C8—H8	119.2	C25—C24—C23	109.6 (3)
C8—C9—C10	119.4 (4)	C27—C24—C23	109.5 (4)
C8—C9—H9	120.3	C24—C25—H25A	109.5
C10—C9—H9	120.3	C24—C25—H25B	109.5
C11—C10—C9	120.6 (4)	H25A—C25—H25B	109.5
C11—C10—H10	119.7	C24—C25—H25C	109.5
C9—C10—H10	119.7	H25A—C25—H25C	109.5
C10—C11—C12	120.1 (4)	H25B—C25—H25C	109.5
C10—C11—H11	120.0	C24—C26—H26A	109.5
C12—C11—H11	120.0	C24—C26—H26B	109.5
O2—C12—C7	121.5 (3)	H26A—C26—H26B	109.5
O2—C12—C11	118.4 (4)	C24—C26—H26C	109.5
C7—C12—C11	120.1 (4)	H26A—C26—H26C	109.5
O3—C13—O4	122.2 (3)	H26B—C26—H26C	109.5
O3—C13—C14	124.7 (4)	C24—C27—H27A	109.5
O4—C13—C14	113.0 (4)	C24—C27—H27B	109.5
C13—C14—C16A	109.4 (8)	H27A—C27—H27B	109.5
C13—C14—C17A	112.1 (7)	C24—C27—H27C	109.5
C16A—C14—C17A	111.4 (9)	H27A—C27—H27C	109.5
C13—C14—C16B	110.9 (8)	H27B—C27—H27C	109.5
C16A—C14—C16B	37.3 (8)	O10—C28—C5	109.6 (3)
C17A—C14—C16B	134.2 (10)	O10—C28—H28A	109.8
C13—C14—C17B	108.5 (7)	C5—C28—H28A	109.8
C16A—C14—C17B	74.8 (9)	O10—C28—H28B	109.8
C17A—C14—C17B	41.5 (8)	C5—C28—H28B	109.8
C16B—C14—C17B	109.0 (10)	H28A—C28—H28B	108.2
C13—C14—C15B	111.4 (6)	O9—C29—O10	120.8 (4)
C16A—C14—C15B	135.6 (9)	O9—C29—C30	125.8 (4)
C17A—C14—C15B	67.7 (8)	O10—C29—C30	113.4 (4)
C16B—C14—C15B	109.6 (8)	C32—C30—C29	108.8 (5)
C17B—C14—C15B	107.3 (9)	C32—C30—C33	111.5 (5)
C13—C14—C15A	101.9 (6)	C29—C30—C33	109.2 (4)
C16A—C14—C15A	109.4 (9)	C32—C30—C31	109.5 (4)
C17A—C14—C15A	112.2 (10)	C29—C30—C31	108.7 (4)
C16B—C14—C15A	72.7 (9)	C33—C30—C31	109.1 (4)
C17B—C14—C15A	146.0 (9)	C30—C31—H31A	109.5
C15B—C14—C15A	45.4 (7)	C30—C31—H31B	109.5
C14—C15A—H15A	109.5	H31A—C31—H31B	109.5
C14—C15A—H15B	109.5	C30—C31—H31C	109.5
C14—C15A—H15C	109.5	H31A—C31—H31C	109.5
C14—C16A—H16A	109.5	H31B—C31—H31C	109.5
C14—C16A—H16B	109.5	C30—C32—H32A	109.5
C14—C16A—H16C	109.5	C30—C32—H32B	109.5
C14—C17A—H17A	109.5	H32A—C32—H32B	109.5
C14—C17A—H17B	109.5	C30—C32—H32C	109.5
C14—C17A—H17C	109.5	H32A—C32—H32C	109.5
C14—C15B—H15D	109.5	H32B—C32—H32C	109.5
C14—C15B—H15E	109.5	C30—C33—H33A	109.5
H15D—C15B—H15E	109.5	C30—C33—H33B	109.5
C14—C15B—H15F	109.5	H33A—C33—H33B	109.5
H15D—C15B—H15F	109.5	C30—C33—H33C	109.5
H15E—C15B—H15F	109.5	H33A—C33—H33C	109.5
C14—C16B—H16D	109.5	H33B—C33—H33C	109.5
C1—C2—C3—C4	55.5 (4)	O1—C1—C2—C3	−61.6 (3)
C2—C3—C4—C5	−53.5 (4)	N1—C6—C7—C12	−3.8 (6)
C3—C4—C5—O1	57.3 (4)	C6—N1—C1—O1	117.0 (3)
C4—C5—O1—C1	−64.3 (3)	C6—N1—C1—C2	−125.6 (3)
C5—O1—C1—C2	66.3 (3)	C7—C12—O2—H2	19.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.92	2.588 (4)	137