Crystal structure of 1,3-bis­(3-tert-butyl-2-hy­droxy-5-methyl­benz­yl)-1,3-diazinan-5-ol monohydrate

The asymmetric unit comprises one 1,3-bis­(3-tert-butyl-2-hy­droxy-5-methyl­benz­yl)-1,3-diazinan-5-ol mol­ecule and one water mol­ecule. The two mol­ecular components are held together through an O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.079
• wR factor = 0.207
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5086

Author Response: Due to the experimental setup the maximal value of 2 theta was restricted to 103 deg. Nevertheless, the resolution is 0.98\%A.

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    --  H1WB   ...     Please Check

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5086
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.4234
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.08 Note
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        4.0 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C27 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00735 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.101 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.508         77 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       7.07 Why ?
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00008 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00030 Ang.
PLAT145_ALERT_4_G s.u. on beta     Small or Missing ..............     0.0004 Degree
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          3 Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          85 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT931_ALERT_5_G Found Twin Law (       )[ 1 0  2] Estimated BASF       0.11 Check
PLAT996_ALERT_1_G Non-Standard SHELXL LIST 4 Style FCF Supplied ..          ! Check

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1,3-Bis(3-tert-butyl-2-hydroxy-5-methylbenzyl)-1,3-diazinan-5-ol monohydrate

Crystal data

C28H42N2O3·H2O	F(000) = 1032
Mr = 472.65	Dx = 1.120 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
a = 10.11944 (9) Å	Cell parameters from 9999 reflections
b = 8.25445 (8) Å	θ = 2–50°
c = 33.8907 (3) Å	µ = 0.59 mm^−1
β = 97.8676 (4)°	T = 173 K
V = 2804.26 (4) Å^3	Plate, colourless
Z = 4	0.25 × 0.25 × 0.09 mm

Data collection

Bruker APEXII CCD three-circle diffractometer	2895 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus source	Rint = 0.053
ω scans	θmax = 51.7°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→10
Tmin = 0.746, Tmax = 1.000	k = −7→8
25653 measured reflections	l = −34→34
3138 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.207	w = 1/[σ^2(Fo^2) + (0.0797P)^2 + 7.0703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3138 reflections	Δρmax = 0.28 e Å^−3
333 parameters	Δρmin = −0.31 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.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.3254 (4)	0.7763 (5)	0.21069 (11)	0.0316 (10)
N2	0.3688 (4)	0.7733 (5)	0.28166 (11)	0.0328 (10)
O1	0.2304 (4)	0.5043 (4)	0.17291 (11)	0.0455 (10)
H1	0.255 (6)	0.578 (8)	0.1942 (19)	0.07 (2)*
O2	0.3143 (3)	0.5008 (4)	0.32058 (10)	0.0400 (9)
H2	0.329 (5)	0.575 (7)	0.2996 (17)	0.056 (17)*
O3	0.0542 (5)	0.9917 (7)	0.25116 (16)	0.0540 (19)	0.794 (13)
H3	0.091 (8)	1.073 (11)	0.251 (2)	0.05 (3)*	0.794 (13)
O3'	0.087 (2)	0.732 (3)	0.2516 (8)	0.084 (10)	0.206 (13)
H3'	0.1248	0.6581	0.2401	0.126*	0.206 (13)
C1	0.4256 (4)	0.8013 (6)	0.24530 (13)	0.0316 (11)
H1A	0.5012	0.7262	0.2441	0.038*
H1B	0.4600	0.9135	0.2451	0.038*
C2	0.2173 (5)	0.8935 (6)	0.21124 (14)	0.0375 (12)
H2A	0.1483	0.8753	0.1880	0.045*
H2B	0.2526	1.0047	0.2094	0.045*
C3	0.1561 (5)	0.8758 (6)	0.24922 (15)	0.0379 (13)
H3A	0.1156	0.7654	0.2495	0.046*	0.794 (13)
H3B	0.0914	0.9667	0.2503	0.046*	0.206 (13)
C4	0.2634 (5)	0.8907 (6)	0.28543 (14)	0.0370 (12)
H4A	0.3007	1.0017	0.2870	0.044*
H4B	0.2240	0.8695	0.3101	0.044*
C6	0.3872 (5)	0.7878 (6)	0.17401 (14)	0.0378 (13)
H6A	0.4694	0.7213	0.1772	0.045*
H6B	0.4135	0.9017	0.1703	0.045*
C7	0.4746 (5)	0.7809 (6)	0.31659 (14)	0.0387 (12)
H7A	0.5061	0.8942	0.3202	0.046*
H7B	0.5512	0.7140	0.3110	0.046*
C11	0.2987 (4)	0.7334 (5)	0.13747 (14)	0.0308 (12)
C12	0.2251 (5)	0.5891 (5)	0.13778 (14)	0.0310 (12)
C13	0.1507 (5)	0.5278 (6)	0.10314 (15)	0.0377 (13)
C14	0.1514 (6)	0.6207 (7)	0.06904 (15)	0.0485 (15)
H14	0.1022	0.5821	0.0450	0.058*
C15	0.2198 (6)	0.7672 (7)	0.06775 (15)	0.0490 (15)
C16	0.2925 (5)	0.8205 (6)	0.10255 (15)	0.0405 (13)
H16	0.3398	0.9199	0.1025	0.049*
C17	0.0760 (5)	0.3666 (6)	0.10303 (17)	0.0499 (15)
C18	0.0022 (8)	0.3268 (9)	0.0615 (2)	0.095 (3)
H18A	−0.0621	0.4130	0.0530	0.143*
H18B	0.0667	0.3184	0.0425	0.143*
H18C	−0.0452	0.2236	0.0625	0.143*
C19	0.1749 (6)	0.2298 (6)	0.1152 (2)	0.071 (2)
H19A	0.1268	0.1267	0.1151	0.106*
H19B	0.2399	0.2240	0.0963	0.106*
H19C	0.2216	0.2508	0.1420	0.106*
C20	−0.0288 (6)	0.3723 (7)	0.1317 (2)	0.0652 (18)
H20A	−0.0921	0.4601	0.1239	0.098*
H20B	−0.0767	0.2689	0.1308	0.098*
H20C	0.0156	0.3915	0.1589	0.098*
C21	0.4305 (4)	0.7238 (5)	0.35448 (14)	0.0292 (11)
C22	0.3553 (4)	0.5812 (5)	0.35560 (13)	0.0259 (11)
C23	0.3228 (4)	0.5197 (6)	0.39176 (13)	0.0307 (11)
C24	0.3686 (6)	0.6071 (7)	0.42536 (15)	0.0469 (14)
H24	0.3490	0.5673	0.4502	0.056*
C25	0.4417 (6)	0.7497 (7)	0.42547 (16)	0.0535 (16)
C26	0.4698 (5)	0.8058 (6)	0.38942 (15)	0.0431 (14)
H26	0.5180	0.9043	0.3886	0.052*
C27	0.2443 (5)	0.3604 (6)	0.39375 (15)	0.0370 (13)
C28	0.1069 (5)	0.3741 (7)	0.36836 (19)	0.0559 (16)
H28A	0.0569	0.4634	0.3783	0.084*
H28B	0.1185	0.3950	0.3406	0.084*
H28C	0.0577	0.2726	0.3700	0.084*
C29	0.3219 (6)	0.2220 (6)	0.3783 (2)	0.0593 (17)
H29A	0.3377	0.2457	0.3510	0.089*
H29B	0.4075	0.2094	0.3954	0.089*
H29C	0.2704	0.1215	0.3786	0.089*
C30	0.2210 (8)	0.3202 (9)	0.4363 (2)	0.081 (2)
H30A	0.1709	0.4084	0.4467	0.121*
H30B	0.1699	0.2193	0.4363	0.121*
H30C	0.3071	0.3072	0.4531	0.121*
C151	0.2103 (9)	0.8663 (9)	0.03030 (18)	0.090 (2)
H15A	0.1229	0.9194	0.0256	0.135*
H15B	0.2211	0.7956	0.0077	0.135*
H15C	0.2807	0.9487	0.0332	0.135*
C251	0.4875 (10)	0.8412 (10)	0.4634 (2)	0.105 (3)
H25A	0.4431	0.9469	0.4625	0.158*
H25B	0.5843	0.8570	0.4660	0.158*
H25C	0.4651	0.7793	0.4862	0.158*
O1W	0.1841 (5)	0.3019 (6)	0.2497 (2)	0.120 (2)
H1WA	0.1012	0.3526	0.2427	0.179*
H1WB	0.2232	0.3920	0.2488	0.179*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.027 (2)	0.028 (2)	0.040 (2)	−0.0053 (18)	0.0046 (18)	−0.0030 (18)
N2	0.031 (2)	0.029 (2)	0.037 (2)	−0.0030 (19)	−0.0001 (18)	0.0044 (18)
O1	0.052 (2)	0.030 (2)	0.053 (2)	−0.0120 (18)	0.0012 (18)	0.0074 (19)
O2	0.048 (2)	0.032 (2)	0.039 (2)	−0.0141 (17)	0.0033 (16)	−0.0058 (17)
O3	0.037 (3)	0.046 (4)	0.080 (4)	0.009 (3)	0.013 (3)	0.000 (3)
O3'	0.054 (15)	0.10 (2)	0.101 (18)	−0.040 (14)	0.025 (12)	−0.002 (15)
C1	0.027 (3)	0.024 (2)	0.044 (3)	−0.003 (2)	0.004 (2)	0.002 (2)
C2	0.034 (3)	0.031 (3)	0.046 (3)	0.005 (2)	0.000 (2)	0.003 (2)
C3	0.024 (3)	0.032 (3)	0.057 (3)	0.012 (3)	0.004 (2)	0.002 (2)
C4	0.034 (3)	0.029 (3)	0.048 (3)	0.004 (2)	0.009 (2)	0.002 (2)
C6	0.036 (3)	0.033 (3)	0.046 (3)	−0.011 (2)	0.010 (2)	0.000 (2)
C7	0.034 (3)	0.030 (3)	0.050 (3)	−0.006 (2)	−0.005 (2)	0.003 (2)
C11	0.030 (3)	0.019 (3)	0.044 (3)	−0.004 (2)	0.010 (2)	−0.006 (2)
C12	0.028 (3)	0.020 (3)	0.045 (3)	0.004 (2)	0.007 (2)	0.003 (2)
C13	0.035 (3)	0.026 (3)	0.052 (3)	0.002 (2)	0.005 (2)	−0.010 (2)
C14	0.052 (4)	0.051 (4)	0.040 (3)	0.001 (3)	−0.001 (3)	−0.014 (3)
C15	0.065 (4)	0.044 (4)	0.040 (3)	−0.002 (3)	0.014 (3)	−0.001 (3)
C16	0.051 (3)	0.030 (3)	0.043 (3)	−0.004 (3)	0.016 (3)	0.001 (2)
C17	0.038 (3)	0.036 (3)	0.073 (4)	−0.004 (3)	−0.001 (3)	−0.016 (3)
C18	0.106 (6)	0.072 (5)	0.100 (6)	−0.043 (5)	−0.015 (5)	−0.030 (4)
C19	0.046 (4)	0.021 (3)	0.148 (6)	−0.001 (3)	0.022 (4)	−0.017 (3)
C20	0.035 (3)	0.041 (4)	0.121 (5)	−0.004 (3)	0.016 (4)	−0.006 (3)
C21	0.022 (3)	0.018 (3)	0.044 (3)	−0.002 (2)	−0.007 (2)	−0.004 (2)
C22	0.023 (3)	0.017 (3)	0.035 (3)	0.004 (2)	−0.007 (2)	−0.008 (2)
C23	0.026 (3)	0.028 (3)	0.038 (3)	0.005 (2)	0.003 (2)	−0.002 (2)
C24	0.059 (4)	0.046 (3)	0.036 (3)	−0.003 (3)	0.009 (3)	−0.005 (3)
C25	0.068 (4)	0.045 (4)	0.044 (3)	−0.008 (3)	−0.002 (3)	−0.021 (3)
C26	0.046 (3)	0.027 (3)	0.053 (4)	−0.007 (3)	−0.006 (3)	−0.010 (3)
C27	0.027 (3)	0.030 (3)	0.055 (3)	0.001 (2)	0.010 (2)	0.005 (2)
C28	0.031 (3)	0.040 (3)	0.098 (5)	−0.004 (3)	0.014 (3)	0.003 (3)
C29	0.048 (4)	0.023 (3)	0.110 (5)	−0.003 (3)	0.022 (3)	0.002 (3)
C30	0.103 (6)	0.069 (5)	0.073 (4)	−0.024 (4)	0.023 (4)	0.014 (4)
C151	0.132 (7)	0.088 (5)	0.048 (4)	−0.009 (5)	0.010 (4)	0.016 (4)
C251	0.157 (8)	0.097 (6)	0.059 (4)	−0.050 (6)	0.006 (5)	−0.036 (4)
O1W	0.081 (4)	0.058 (3)	0.220 (7)	−0.002 (3)	0.022 (4)	−0.010 (4)

Geometric parameters (Å, º)

N1—C1	1.456 (6)	C17—C20	1.535 (8)
N1—C2	1.462 (6)	C17—C18	1.536 (8)
N1—C6	1.469 (6)	C18—H18A	0.9800
N2—C1	1.448 (6)	C18—H18B	0.9800
N2—C4	1.460 (6)	C18—H18C	0.9800
N2—C7	1.485 (6)	C19—H19A	0.9800
O1—C12	1.376 (6)	C19—H19B	0.9800
O1—H1	0.95 (7)	C19—H19C	0.9800
O2—C22	1.374 (5)	C20—H20A	0.9800
O2—H2	0.96 (6)	C20—H20B	0.9800
O3—C3	1.415 (6)	C20—H20C	0.9800
O3—H3	0.76 (9)	C21—C26	1.375 (7)
O3'—C3	1.38 (2)	C21—C22	1.405 (6)
O3'—H3'	0.8400	C22—C23	1.407 (6)
C1—H1A	0.9900	C23—C24	1.374 (7)
C1—H1B	0.9900	C23—C27	1.542 (7)
C2—C3	1.510 (7)	C24—C25	1.390 (8)
C2—H2A	0.9900	C24—H24	0.9500
C2—H2B	0.9900	C25—C26	1.372 (8)
C3—C4	1.528 (7)	C25—C251	1.507 (8)
C3—H3A	1.0000	C26—H26	0.9500
C3—H3B	1.0000	C27—C29	1.519 (7)
C4—H4A	0.9900	C27—C30	1.529 (8)
C4—H4B	0.9900	C27—C28	1.536 (7)
C6—C11	1.494 (7)	C28—H28A	0.9800
C6—H6A	0.9900	C28—H28B	0.9800
C6—H6B	0.9900	C28—H28C	0.9800
C7—C21	1.493 (7)	C29—H29A	0.9800
C7—H7A	0.9900	C29—H29B	0.9800
C7—H7B	0.9900	C29—H29C	0.9800
C11—C16	1.378 (7)	C30—H30A	0.9800
C11—C12	1.406 (6)	C30—H30B	0.9800
C12—C13	1.400 (7)	C30—H30C	0.9800
C13—C14	1.388 (7)	C151—H15A	0.9800
C13—C17	1.530 (7)	C151—H15B	0.9800
C14—C15	1.397 (8)	C151—H15C	0.9800
C14—H14	0.9500	C251—H25A	0.9800
C15—C16	1.374 (7)	C251—H25B	0.9800
C15—C151	1.502 (8)	C251—H25C	0.9800
C16—H16	0.9500	O1W—H1WA	0.9381
C17—C19	1.528 (8)	O1W—H1WB	0.8447
C1—N1—C2	109.6 (4)	C20—C17—C18	107.2 (5)
C1—N1—C6	110.0 (3)	C17—C18—H18A	109.5
C2—N1—C6	111.9 (4)	C17—C18—H18B	109.5
C1—N2—C4	110.4 (4)	H18A—C18—H18B	109.5
C1—N2—C7	110.2 (4)	C17—C18—H18C	109.5
C4—N2—C7	111.0 (4)	H18A—C18—H18C	109.5
C12—O1—H1	108 (4)	H18B—C18—H18C	109.5
C22—O2—H2	106 (3)	C17—C19—H19A	109.5
C3—O3—H3	104 (6)	C17—C19—H19B	109.5
C3—O3'—H3'	109.5	H19A—C19—H19B	109.5
N2—C1—N1	110.5 (3)	C17—C19—H19C	109.5
N2—C1—H1A	109.6	H19A—C19—H19C	109.5
N1—C1—H1A	109.6	H19B—C19—H19C	109.5
N2—C1—H1B	109.6	C17—C20—H20A	109.5
N1—C1—H1B	109.6	C17—C20—H20B	109.5
H1A—C1—H1B	108.1	H20A—C20—H20B	109.5
N1—C2—C3	110.0 (4)	C17—C20—H20C	109.5
N1—C2—H2A	109.7	H20A—C20—H20C	109.5
C3—C2—H2A	109.7	H20B—C20—H20C	109.5
N1—C2—H2B	109.7	C26—C21—C22	118.9 (4)
C3—C2—H2B	109.7	C26—C21—C7	120.0 (4)
H2A—C2—H2B	108.2	C22—C21—C7	121.0 (4)
O3'—C3—C2	113.6 (11)	O2—C22—C21	118.8 (4)
O3—C3—C2	111.2 (4)	O2—C22—C23	119.9 (4)
O3'—C3—C4	109.2 (12)	C21—C22—C23	121.2 (4)
O3—C3—C4	110.5 (4)	C24—C23—C22	116.1 (4)
C2—C3—C4	110.4 (4)	C24—C23—C27	121.9 (4)
O3—C3—H3A	108.2	C22—C23—C27	122.0 (4)
C2—C3—H3A	108.2	C23—C24—C25	124.5 (5)
C4—C3—H3A	108.2	C23—C24—H24	117.8
O3'—C3—H3B	107.8	C25—C24—H24	117.8
C2—C3—H3B	107.8	C26—C25—C24	117.3 (5)
C4—C3—H3B	107.8	C26—C25—C251	120.8 (6)
N2—C4—C3	108.9 (4)	C24—C25—C251	121.9 (6)
N2—C4—H4A	109.9	C25—C26—C21	122.0 (5)
C3—C4—H4A	109.9	C25—C26—H26	119.0
N2—C4—H4B	109.9	C21—C26—H26	119.0
C3—C4—H4B	109.9	C29—C27—C30	108.3 (5)
H4A—C4—H4B	108.3	C29—C27—C28	109.5 (5)
N1—C6—C11	114.0 (4)	C30—C27—C28	107.4 (5)
N1—C6—H6A	108.8	C29—C27—C23	109.4 (4)
C11—C6—H6A	108.8	C30—C27—C23	111.9 (4)
N1—C6—H6B	108.8	C28—C27—C23	110.2 (4)
C11—C6—H6B	108.8	C27—C28—H28A	109.5
H6A—C6—H6B	107.7	C27—C28—H28B	109.5
N2—C7—C21	113.8 (4)	H28A—C28—H28B	109.5
N2—C7—H7A	108.8	C27—C28—H28C	109.5
C21—C7—H7A	108.8	H28A—C28—H28C	109.5
N2—C7—H7B	108.8	H28B—C28—H28C	109.5
C21—C7—H7B	108.8	C27—C29—H29A	109.5
H7A—C7—H7B	107.7	C27—C29—H29B	109.5
C16—C11—C12	119.1 (4)	H29A—C29—H29B	109.5
C16—C11—C6	120.4 (4)	C27—C29—H29C	109.5
C12—C11—C6	120.4 (4)	H29A—C29—H29C	109.5
O1—C12—C13	119.6 (4)	H29B—C29—H29C	109.5
O1—C12—C11	118.7 (4)	C27—C30—H30A	109.5
C13—C12—C11	121.6 (4)	C27—C30—H30B	109.5
C14—C13—C12	115.8 (4)	H30A—C30—H30B	109.5
C14—C13—C17	122.5 (5)	C27—C30—H30C	109.5
C12—C13—C17	121.7 (5)	H30A—C30—H30C	109.5
C13—C14—C15	124.3 (5)	H30B—C30—H30C	109.5
C13—C14—H14	117.8	C15—C151—H15A	109.5
C15—C14—H14	117.8	C15—C151—H15B	109.5
C16—C15—C14	117.3 (5)	H15A—C151—H15B	109.5
C16—C15—C151	121.0 (5)	C15—C151—H15C	109.5
C14—C15—C151	121.6 (5)	H15A—C151—H15C	109.5
C15—C16—C11	121.8 (5)	H15B—C151—H15C	109.5
C15—C16—H16	119.1	C25—C251—H25A	109.5
C11—C16—H16	119.1	C25—C251—H25B	109.5
C19—C17—C13	109.7 (4)	H25A—C251—H25B	109.5
C19—C17—C20	109.6 (5)	C25—C251—H25C	109.5
C13—C17—C20	110.8 (4)	H25A—C251—H25C	109.5
C19—C17—C18	107.9 (5)	H25B—C251—H25C	109.5
C13—C17—C18	111.5 (5)	H1WA—O1W—H1WB	90.3
C4—N2—C1—N1	−63.3 (5)	C151—C15—C16—C11	177.9 (6)
C7—N2—C1—N1	173.7 (4)	C12—C11—C16—C15	−2.2 (7)
C2—N1—C1—N2	62.5 (5)	C6—C11—C16—C15	175.2 (5)
C6—N1—C1—N2	−174.0 (4)	C14—C13—C17—C19	118.1 (6)
C1—N1—C2—C3	−58.2 (5)	C12—C13—C17—C19	−60.6 (6)
C6—N1—C2—C3	179.4 (4)	C14—C13—C17—C20	−120.7 (6)
N1—C2—C3—O3'	−68.0 (13)	C12—C13—C17—C20	60.6 (6)
N1—C2—C3—O3	178.0 (4)	C14—C13—C17—C18	−1.4 (7)
N1—C2—C3—C4	55.0 (5)	C12—C13—C17—C18	179.9 (5)
C1—N2—C4—C3	58.5 (5)	N2—C7—C21—C26	−139.0 (4)
C7—N2—C4—C3	−179.0 (4)	N2—C7—C21—C22	44.8 (6)
O3'—C3—C4—N2	70.9 (11)	C26—C21—C22—O2	179.0 (4)
O3—C3—C4—N2	−178.0 (4)	C7—C21—C22—O2	−4.8 (6)
C2—C3—C4—N2	−54.7 (5)	C26—C21—C22—C23	−1.5 (6)
C1—N1—C6—C11	169.1 (4)	C7—C21—C22—C23	174.7 (4)
C2—N1—C6—C11	−68.8 (5)	O2—C22—C23—C24	179.6 (4)
C1—N2—C7—C21	−169.3 (4)	C21—C22—C23—C24	0.1 (6)
C4—N2—C7—C21	68.0 (5)	O2—C22—C23—C27	1.5 (6)
N1—C6—C11—C16	137.4 (5)	C21—C22—C23—C27	−178.0 (4)
N1—C6—C11—C12	−45.3 (6)	C22—C23—C24—C25	0.8 (8)
C16—C11—C12—O1	−179.0 (4)	C27—C23—C24—C25	178.9 (5)
C6—C11—C12—O1	3.6 (6)	C23—C24—C25—C26	−0.2 (9)
C16—C11—C12—C13	3.0 (7)	C23—C24—C25—C251	179.2 (6)
C6—C11—C12—C13	−174.3 (4)	C24—C25—C26—C21	−1.3 (8)
O1—C12—C13—C14	−179.7 (4)	C251—C25—C26—C21	179.3 (6)
C11—C12—C13—C14	−1.8 (7)	C22—C21—C26—C25	2.2 (7)
O1—C12—C13—C17	−0.9 (7)	C7—C21—C26—C25	−174.1 (5)
C11—C12—C13—C17	177.0 (4)	C24—C23—C27—C29	−117.7 (5)
C12—C13—C14—C15	−0.3 (8)	C22—C23—C27—C29	60.2 (6)
C17—C13—C14—C15	−179.1 (5)	C24—C23—C27—C30	2.3 (7)
C13—C14—C15—C16	1.1 (8)	C22—C23—C27—C30	−179.7 (5)
C13—C14—C15—C151	−176.6 (6)	C24—C23—C27—C28	121.8 (5)
C14—C15—C16—C11	0.2 (8)	C22—C23—C27—C28	−60.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95 (7)	1.84 (7)	2.696 (5)	148 (5)
O2—H2···N2	0.96 (6)	1.81 (6)	2.702 (5)	152 (5)
O3—H3···O1W^i	0.76 (9)	2.12 (9)	2.882 (8)	177 (9)
O1W—H1WA···O3^ii	0.94	1.98	2.873 (8)	158
O1W—H1WA···O3′^ii	0.94	2.19	2.80 (2)	122
O1W—H1WB···O2	0.84	2.64	3.057 (7)	112

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