N-(2-Hydr­oxy-3-methoxy­benzyl­idene)-2,3,4,6-tetra-O-acetyl-β-D-galactopyran­osylamine

In the title compound, C₂₂H₂₇NO₁₁, the pyranosyl ring has a chair conformation. In the crystal structure, inter­molecular O—H...N and C—H...O hydrogen-bonding inter­actions are observed as well as intra­molecular C—H...O hydrogen-bond contacts.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.094
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.102
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.95 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.15
           From the CIF: _reflns_number_total               2862
           Count of symmetry unique reflns         2919
           Completeness (_total/calc)             98.05%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).

N-(2-Hydroxy-3-methoxybenzylidene)-2,3,4,6-tetra-O-acetyl-β-D– galactopyranosylamine

Crystal data

C22H27NO11	F(000) = 508
Mr = 481.45	Dx = 1.303 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 21812 reflections
a = 8.6855 (7) Å	θ = 2.2–27.2°
b = 7.6735 (5) Å	µ = 0.11 mm^−1
c = 18.5577 (15) Å	T = 296 K
β = 97.124 (7)°	Prism, pale yellow
V = 1227.29 (16) Å^3	0.66 × 0.55 × 0.42 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	2862 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2154 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.102
Detector resolution: 6.67 pixels mm^-1	θmax = 27.2°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.934, Tmax = 0.957	l = −23→23
19328 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0717P)^2] where P = (Fo^2 + 2Fc^2)/3
2862 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.12 e Å^−3

Special details

Experimental. 1^{H NMR (CDCl₃, 250 MHz): δ 12.44 (OH, br, 1H), 8.53 (NCH, s, 1H), 7.22–6.77 (Ar—H, m, 4H), 5.43–4.07 (sugar protons, m, 7H), 3.86 (OCH₃, s, 3H), 2.10–1.91 (4COCH₃, s, 12H).}

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.1233 (2)	0.0274 (3)	0.29799 (9)	0.0850 (7)
O2	0.0715 (3)	−0.2558 (3)	0.37031 (12)	0.1042 (8)
O3	0.41693 (17)	0.5852 (2)	0.30318 (8)	0.0680 (5)
O4	0.20344 (16)	0.3813 (2)	0.14296 (8)	0.0646 (5)
O5	0.3112 (2)	0.1163 (2)	0.15940 (10)	0.0864 (7)
O6	0.41831 (18)	0.5981 (2)	0.08216 (8)	0.0704 (5)
O7	0.2560 (3)	0.7945 (4)	0.02734 (11)	0.1135 (9)
O8	0.63452 (16)	0.6512 (2)	0.20102 (9)	0.0712 (5)
O9	0.7161 (3)	0.8402 (5)	0.1227 (2)	0.1598 (13)
O10	0.6118 (3)	0.9918 (3)	0.29638 (11)	0.0996 (7)
O11	0.7726 (4)	1.0445 (4)	0.39474 (15)	0.1350 (11)
N1	0.2551 (2)	0.3374 (3)	0.29719 (10)	0.0659 (6)
C1	0.1879 (2)	0.0179 (3)	0.36813 (12)	0.0674 (7)
C2	0.1620 (3)	−0.1314 (4)	0.40754 (14)	0.0761 (8)
C3	0.2265 (3)	−0.1458 (4)	0.47863 (15)	0.0835 (9)
C4	0.3187 (3)	−0.0145 (4)	0.51165 (14)	0.0838 (9)
C5	0.3455 (3)	0.1324 (4)	0.47363 (13)	0.0800 (9)
C6	0.2806 (2)	0.1514 (3)	0.40134 (12)	0.0660 (7)
C7	0.3117 (2)	0.3090 (3)	0.36271 (12)	0.0679 (7)
C8	0.0090 (5)	−0.3866 (5)	0.4112 (2)	0.1257 (16)
C9	0.2914 (2)	0.4968 (3)	0.26257 (11)	0.0622 (6)
C10	0.3333 (2)	0.4598 (3)	0.18607 (11)	0.0590 (6)
C11	0.3655 (2)	0.6325 (3)	0.15076 (11)	0.0606 (6)
C12	0.4865 (2)	0.7385 (3)	0.19760 (12)	0.0634 (6)
C13	0.4431 (3)	0.7532 (3)	0.27383 (12)	0.0681 (7)
C14	0.2067 (3)	0.2048 (3)	0.13339 (12)	0.0700 (8)
C15	0.0642 (4)	0.1434 (5)	0.0887 (2)	0.1135 (14)
C16	0.3609 (3)	0.6964 (3)	0.02508 (12)	0.0714 (7)
C17	0.4463 (4)	0.6697 (4)	−0.03810 (15)	0.0993 (12)
C18	0.7392 (3)	0.7184 (5)	0.1608 (2)	0.1051 (13)
C19	0.8852 (4)	0.6181 (9)	0.1712 (4)	0.174 (3)
C20	0.5656 (4)	0.8329 (4)	0.32826 (15)	0.0865 (9)
C21	0.7168 (3)	1.0872 (4)	0.33424 (18)	0.0925 (10)
C22	0.7587 (5)	1.2420 (5)	0.2928 (3)	0.1293 (18)
HO1	0.160 (4)	0.130 (6)	0.2814 (19)	0.108 (11)*
H3	0.20800	−0.24520	0.50490	0.1000*
H4	0.36260	−0.02630	0.55970	0.1010*
H5	0.40740	0.22060	0.49600	0.0960*
H7	0.37590	0.39310	0.38680	0.0820*
H8A	0.09100	−0.46090	0.43280	0.1880*
H8B	−0.06450	−0.45440	0.38000	0.1880*
H8C	−0.04200	−0.33380	0.44870	0.1880*
H9	0.19990	0.57260	0.25840	0.0750*
H10	0.42440	0.38350	0.18850	0.0710*
H11	0.26890	0.69960	0.14270	0.0730*
H12	0.49390	0.85500	0.17670	0.0760*
H13	0.34780	0.82220	0.27240	0.0820*
H15A	0.08590	0.03710	0.06460	0.1700*
H15B	0.02960	0.23030	0.05310	0.1700*
H15C	−0.01530	0.12300	0.11930	0.1700*
H17A	0.39140	0.58730	−0.07070	0.1490*
H17B	0.54820	0.62580	−0.02180	0.1490*
H17C	0.45470	0.77850	−0.06280	0.1490*
H19A	0.97170	0.69690	0.17560	0.2610*
H19B	0.89040	0.54290	0.13020	0.2610*
H19C	0.88850	0.54920	0.21460	0.2610*
H20A	0.52410	0.85670	0.37340	0.1040*
H20B	0.65340	0.75480	0.33820	0.1040*
H22A	0.69060	1.33690	0.30070	0.1940*
H22B	0.74870	1.21440	0.24200	0.1940*
H22C	0.86400	1.27490	0.30910	0.1940*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0931 (11)	0.0980 (14)	0.0636 (9)	−0.0178 (10)	0.0090 (8)	−0.0008 (9)
O2	0.1298 (16)	0.0913 (14)	0.0980 (12)	−0.0305 (13)	0.0394 (12)	−0.0085 (11)
O3	0.0729 (8)	0.0670 (9)	0.0624 (8)	−0.0018 (7)	0.0016 (6)	0.0050 (7)
O4	0.0594 (7)	0.0658 (9)	0.0670 (8)	0.0075 (6)	0.0018 (6)	−0.0031 (7)
O5	0.0997 (12)	0.0720 (11)	0.0861 (11)	0.0211 (10)	0.0063 (9)	−0.0054 (9)
O6	0.0789 (8)	0.0729 (9)	0.0624 (8)	0.0165 (8)	0.0208 (7)	0.0068 (7)
O7	0.1490 (18)	0.1149 (16)	0.0732 (10)	0.0576 (17)	−0.0001 (11)	0.0093 (11)
O8	0.0554 (7)	0.0668 (9)	0.0910 (10)	0.0106 (6)	0.0080 (7)	0.0204 (8)
O9	0.1083 (15)	0.151 (2)	0.233 (3)	0.0318 (16)	0.0726 (18)	0.114 (3)
O10	0.1191 (14)	0.0716 (11)	0.0990 (13)	−0.0184 (11)	−0.0226 (11)	0.0099 (10)
O11	0.165 (2)	0.122 (2)	0.1081 (17)	−0.0276 (18)	−0.0227 (16)	−0.0302 (16)
N1	0.0664 (9)	0.0716 (12)	0.0612 (10)	0.0020 (8)	0.0135 (8)	0.0040 (8)
C1	0.0652 (11)	0.0789 (14)	0.0602 (11)	−0.0013 (10)	0.0161 (9)	−0.0013 (10)
C2	0.0767 (13)	0.0748 (14)	0.0812 (15)	−0.0030 (12)	0.0273 (11)	−0.0031 (13)
C3	0.0892 (15)	0.0836 (16)	0.0830 (16)	0.0107 (14)	0.0314 (13)	0.0199 (14)
C4	0.0778 (14)	0.107 (2)	0.0665 (13)	0.0040 (15)	0.0081 (11)	0.0182 (14)
C5	0.0752 (13)	0.0996 (19)	0.0648 (12)	−0.0069 (13)	0.0069 (10)	0.0083 (13)
C6	0.0617 (10)	0.0779 (14)	0.0595 (10)	−0.0020 (10)	0.0116 (8)	0.0034 (10)
C7	0.0634 (11)	0.0771 (14)	0.0635 (12)	−0.0039 (10)	0.0088 (9)	0.0032 (10)
C8	0.152 (3)	0.090 (2)	0.145 (3)	−0.038 (2)	0.058 (2)	−0.005 (2)
C9	0.0585 (10)	0.0671 (12)	0.0609 (10)	0.0030 (10)	0.0068 (8)	0.0015 (9)
C10	0.0542 (9)	0.0621 (11)	0.0595 (10)	0.0093 (9)	0.0029 (8)	0.0009 (9)
C11	0.0585 (9)	0.0643 (12)	0.0597 (10)	0.0139 (9)	0.0100 (8)	0.0055 (9)
C12	0.0584 (10)	0.0573 (11)	0.0735 (12)	0.0104 (8)	0.0041 (9)	0.0108 (9)
C13	0.0760 (12)	0.0616 (12)	0.0654 (11)	0.0050 (10)	0.0036 (10)	0.0011 (10)
C14	0.0749 (13)	0.0683 (14)	0.0681 (13)	0.0088 (11)	0.0137 (10)	−0.0053 (11)
C15	0.0966 (19)	0.096 (2)	0.141 (3)	−0.0001 (17)	−0.0129 (18)	−0.034 (2)
C16	0.0993 (15)	0.0553 (12)	0.0580 (11)	−0.0011 (12)	0.0035 (10)	−0.0017 (9)
C17	0.151 (3)	0.0804 (16)	0.0714 (14)	−0.0128 (18)	0.0330 (16)	−0.0010 (13)
C18	0.0687 (14)	0.106 (2)	0.145 (3)	0.0168 (15)	0.0302 (16)	0.050 (2)
C19	0.0771 (18)	0.202 (5)	0.253 (6)	0.051 (3)	0.062 (3)	0.114 (5)
C20	0.1083 (18)	0.0711 (16)	0.0751 (14)	−0.0069 (14)	−0.0083 (13)	0.0036 (12)
C21	0.0965 (17)	0.0746 (16)	0.102 (2)	−0.0019 (14)	−0.0048 (15)	−0.0259 (15)
C22	0.131 (3)	0.0714 (18)	0.183 (4)	−0.0201 (19)	0.010 (3)	−0.013 (2)

Geometric parameters (Å, º)

O1—C1	1.354 (3)	C13—C20	1.503 (4)
O2—C2	1.368 (4)	C14—C15	1.479 (4)
O2—C8	1.407 (5)	C16—C17	1.477 (4)
O3—C9	1.419 (2)	C18—C19	1.475 (6)
O3—C13	1.429 (3)	C21—C22	1.485 (5)
O4—C10	1.432 (2)	C3—H3	0.9300
O4—C14	1.367 (3)	C4—H4	0.9300
O5—C14	1.187 (3)	C5—H5	0.9300
O6—C11	1.430 (2)	C7—H7	0.9300
O6—C16	1.345 (3)	C8—H8A	0.9600
O7—C16	1.187 (4)	C8—H8B	0.9600
O8—C12	1.444 (2)	C8—H8C	0.9600
O8—C18	1.348 (4)	C9—H9	0.9800
O9—C18	1.174 (5)	C10—H10	0.9800
O10—C20	1.434 (4)	C11—H11	0.9800
O10—C21	1.305 (4)	C12—H12	0.9800
O11—C21	1.212 (4)	C13—H13	0.9800
O1—HO1	0.92 (4)	C15—H15A	0.9600
N1—C9	1.435 (3)	C15—H15B	0.9600
N1—C7	1.273 (3)	C15—H15C	0.9600
C1—C2	1.392 (4)	C17—H17A	0.9600
C1—C6	1.398 (3)	C17—H17B	0.9600
C2—C3	1.372 (4)	C17—H17C	0.9600
C3—C4	1.382 (4)	C19—H19A	0.9600
C4—C5	1.365 (4)	C19—H19B	0.9600
C5—C6	1.397 (3)	C19—H19C	0.9600
C6—C7	1.448 (3)	C20—H20A	0.9700
C9—C10	1.535 (3)	C20—H20B	0.9700
C10—C11	1.520 (3)	C22—H22A	0.9600
C11—C12	1.515 (3)	C22—H22B	0.9600
C12—C13	1.513 (3)	C22—H22C	0.9600
O1···O2	2.622 (3)	C4···H8C^ix	2.9500
O1···N1	2.641 (3)	C7···HO1	2.33 (4)
O2···O1	2.622 (3)	C7···H8A^vii	3.0200
O3···O8	2.883 (2)	C8···H3	2.5400
O4···O6	2.837 (2)	C9···HO1	3.07 (4)
O4···C19^i	3.402 (5)	C14···HO1	2.88 (4)
O4···N1	2.862 (2)	C19···H9^xi	3.0200
O5···C17^ii	3.294 (4)	C22···H19C^vii	3.0600
O5···C12^iii	3.310 (3)	HO1···O5	2.76 (4)
O5···N1	3.157 (3)	HO1···N1	1.80 (4)
O6···O8	2.744 (2)	HO1···C7	2.33 (4)
O6···C18	3.121 (3)	HO1···C9	3.07 (4)
O6···O9	3.198 (4)	HO1···C14	2.88 (4)
O6···O4	2.837 (2)	H3···C8	2.5400
O8···O3	2.883 (2)	H3···H8A	2.2900
O8···O10	3.176 (3)	H3···H8C	2.3900
O8···O6	2.744 (2)	H3···O11^viii	2.4500
O9···O6	3.198 (4)	H4···H7^xii	2.4400
O9···C17^iv	3.209 (5)	H5···H7	2.4100
O10···O8	3.176 (3)	H7···O3	2.2000
O11···C3^v	3.342 (4)	H7···H5	2.4100
O1···H13^iii	2.6000	H7···H4^xiii	2.4400
O2···H9^iii	2.8000	H8A···C3	2.7800
O3···H7	2.2000	H8A···C7^iii	3.0200
O5···H12^iii	2.5500	H8A···H3	2.2900
O5···HO1	2.76 (4)	H8B···H22C^xiv	2.5000
O5···H10	2.3100	H8C···C3	2.7400
O6···H17C^ii	2.7300	H8C···H3	2.3900
O7···H11	2.2500	H8C···C4^x	2.9500
O7···H15B^vi	2.7800	H9···O2^vii	2.8000
O7···H15A^vii	2.5300	H9···C19^i	3.0200
O8···H20B	2.6500	H9···H11	2.5000
O8···H10	2.7400	H9···H13	2.3000
O9···H17A^iv	2.2700	H9···H19A^i	2.5400
O9···H12	2.2900	H10···O5	2.3100
O10···H12	2.5500	H10···O8	2.7400
O11···H20A	2.5800	H11···O7	2.2500
O11···H20B	2.6200	H11···H9	2.5000
O11···H3^v	2.4500	H11···H13	2.6000
N1···O1	2.641 (3)	H12···O5^vii	2.5500
N1···O4	2.862 (2)	H12···O9	2.2900
N1···O5	3.157 (3)	H12···O10	2.5500
N1···C14	3.184 (3)	H13···O1^vii	2.6000
N1···HO1	1.80 (4)	H13···C1^vii	2.8200
C3···O11^viii	3.342 (4)	H13···H9	2.3000
C4···C8^ix	3.482 (5)	H13···H11	2.6000
C8···C4^x	3.482 (5)	H15A···O7^iii	2.5300
C12···O5^vii	3.310 (3)	H15B···O7^xv	2.7800
C14···N1	3.184 (3)	H17A···O9^ii	2.2700
C17···O9^ii	3.209 (5)	H17C···O6^iv	2.7300
C17···O5^iv	3.294 (4)	H19A···H9^xi	2.5400
C18···O6	3.121 (3)	H19C···C22^iii	3.0600
C19···O4^xi	3.402 (5)	H20A···O11	2.5800
C1···H13^iii	2.8200	H20B···O8	2.6500
C3···H8C	2.7400	H20B···O11	2.6200
C3···H8A	2.7800	H22C···H8B^xvi	2.5000
C2—O2—C8	117.5 (2)	C6—C5—H5	120.00
C9—O3—C13	112.15 (16)	N1—C7—H7	119.00
C10—O4—C14	117.50 (17)	C6—C7—H7	119.00
C11—O6—C16	117.97 (17)	O2—C8—H8A	109.00
C12—O8—C18	117.1 (2)	O2—C8—H8B	109.00
C20—O10—C21	117.9 (2)	O2—C8—H8C	109.00
C1—O1—HO1	104 (2)	H8A—C8—H8B	109.00
C7—N1—C9	119.6 (2)	H8A—C8—H8C	109.00
O1—C1—C6	122.1 (2)	H8B—C8—H8C	110.00
C2—C1—C6	119.5 (2)	O3—C9—H9	109.00
O1—C1—C2	118.3 (2)	N1—C9—H9	109.00
O2—C2—C3	124.7 (3)	C10—C9—H9	109.00
C1—C2—C3	119.9 (3)	O4—C10—H10	110.00
O2—C2—C1	115.4 (2)	C9—C10—H10	111.00
C2—C3—C4	120.8 (3)	C11—C10—H10	110.00
C3—C4—C5	120.0 (2)	O6—C11—H11	109.00
C4—C5—C6	120.6 (2)	C10—C11—H11	109.00
C1—C6—C5	119.3 (2)	C12—C11—H11	109.00
C5—C6—C7	119.0 (2)	O8—C12—H12	110.00
C1—C6—C7	121.8 (2)	C11—C12—H12	110.00
N1—C7—C6	122.8 (2)	C13—C12—H12	110.00
O3—C9—C10	108.96 (15)	O3—C13—H13	109.00
N1—C9—C10	110.30 (18)	C12—C13—H13	109.00
O3—C9—N1	111.52 (16)	C20—C13—H13	109.00
O4—C10—C11	107.47 (16)	C14—C15—H15A	109.00
C9—C10—C11	108.36 (18)	C14—C15—H15B	109.00
O4—C10—C9	109.50 (15)	C14—C15—H15C	109.00
O6—C11—C12	109.49 (15)	H15A—C15—H15B	109.00
C10—C11—C12	111.87 (17)	H15A—C15—H15C	110.00
O6—C11—C10	108.62 (17)	H15B—C15—H15C	109.00
O8—C12—C11	109.06 (17)	C16—C17—H17A	109.00
C11—C12—C13	109.94 (17)	C16—C17—H17B	109.00
O8—C12—C13	108.50 (18)	C16—C17—H17C	110.00
O3—C13—C12	111.05 (18)	H17A—C17—H17B	110.00
C12—C13—C20	114.9 (2)	H17A—C17—H17C	109.00
O3—C13—C20	104.11 (19)	H17B—C17—H17C	110.00
O4—C14—C15	111.1 (2)	C18—C19—H19A	109.00
O5—C14—C15	126.2 (2)	C18—C19—H19B	110.00
O4—C14—O5	122.8 (2)	C18—C19—H19C	109.00
O6—C16—C17	111.9 (2)	H19A—C19—H19B	109.00
O7—C16—C17	125.4 (2)	H19A—C19—H19C	109.00
O6—C16—O7	122.6 (2)	H19B—C19—H19C	110.00
O8—C18—C19	110.8 (4)	O10—C20—H20A	110.00
O9—C18—C19	125.0 (4)	O10—C20—H20B	111.00
O8—C18—O9	124.1 (3)	C13—C20—H20A	110.00
O10—C20—C13	106.2 (2)	C13—C20—H20B	111.00
O10—C21—C22	111.7 (3)	H20A—C20—H20B	109.00
O11—C21—C22	126.9 (3)	C21—C22—H22A	109.00
O10—C21—O11	121.3 (3)	C21—C22—H22B	110.00
C2—C3—H3	120.00	C21—C22—H22C	109.00
C4—C3—H3	120.00	H22A—C22—H22B	110.00
C3—C4—H4	120.00	H22A—C22—H22C	109.00
C5—C4—H4	120.00	H22B—C22—H22C	110.00
C4—C5—H5	120.00
C8—O2—C2—C1	−164.0 (3)	C6—C1—C2—O2	−179.2 (2)
C8—O2—C2—C3	16.3 (4)	C2—C1—C6—C5	−0.1 (3)
C9—O3—C13—C20	173.65 (19)	C6—C1—C2—C3	0.5 (4)
C13—O3—C9—N1	−173.39 (17)	C1—C2—C3—C4	−0.7 (4)
C13—O3—C9—C10	64.6 (2)	O2—C2—C3—C4	179.0 (3)
C9—O3—C13—C12	−62.2 (2)	C2—C3—C4—C5	0.5 (4)
C10—O4—C14—O5	0.4 (3)	C3—C4—C5—C6	−0.1 (4)
C14—O4—C10—C11	141.45 (18)	C4—C5—C6—C7	−179.9 (2)
C14—O4—C10—C9	−101.1 (2)	C4—C5—C6—C1	−0.1 (4)
C10—O4—C14—C15	179.2 (2)	C1—C6—C7—N1	1.3 (3)
C16—O6—C11—C12	−100.9 (2)	C5—C6—C7—N1	−178.9 (2)
C11—O6—C16—O7	−9.3 (4)	O3—C9—C10—C11	−59.1 (2)
C16—O6—C11—C10	136.68 (18)	N1—C9—C10—O4	61.2 (2)
C11—O6—C16—C17	169.2 (2)	N1—C9—C10—C11	178.15 (15)
C18—O8—C12—C13	−136.1 (2)	O3—C9—C10—O4	−176.06 (16)
C12—O8—C18—O9	−1.4 (5)	O4—C10—C11—O6	−66.98 (18)
C12—O8—C18—C19	178.7 (3)	C9—C10—C11—C12	53.8 (2)
C18—O8—C12—C11	104.2 (2)	C9—C10—C11—O6	174.78 (14)
C20—O10—C21—C22	176.9 (3)	O4—C10—C11—C12	172.05 (15)
C20—O10—C21—O11	−0.8 (4)	O6—C11—C12—C13	−171.74 (17)
C21—O10—C20—C13	179.0 (2)	O6—C11—C12—O8	−52.9 (2)
C7—N1—C9—C10	134.62 (19)	C10—C11—C12—C13	−51.3 (2)
C9—N1—C7—C6	−179.97 (18)	C10—C11—C12—O8	67.6 (2)
C7—N1—C9—O3	13.4 (3)	C11—C12—C13—C20	171.5 (2)
O1—C1—C2—C3	179.6 (2)	C11—C12—C13—O3	53.7 (2)
O1—C1—C2—O2	−0.1 (3)	O8—C12—C13—C20	52.3 (3)
C2—C1—C6—C7	179.7 (2)	O8—C12—C13—O3	−65.5 (2)
O1—C1—C6—C5	−179.1 (2)	C12—C13—C20—O10	50.4 (3)
O1—C1—C6—C7	0.7 (3)	O3—C13—C20—O10	172.1 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···N1	0.92 (4)	1.80 (4)	2.641 (3)	151 (3)
C3—H3···O11^viii	0.93	2.45	3.342 (4)	160
C7—H7···O3	0.93	2.20	2.607 (3)	105
C10—H10···O5	0.98	2.31	2.684 (3)	102
C11—H11···O7	0.98	2.25	2.675 (3)	105
C12—H12···O5^vii	0.98	2.55	3.310 (3)	134
C12—H12···O9	0.98	2.29	2.684 (4)	103
C13—H13···O1^vii	0.98	2.60	3.557 (3)	167
C15—H15A···O7^iii	0.96	2.53	3.422 (5)	155
C17—H17A···O9^ii	0.96	2.27	3.209 (5)	164

Symmetry codes: (ii) −x+1, y−1/2, −z; (iii) x, y−1, z; (vii) x, y+1, z; (viii) −x+1, y−3/2, −z+1.