1-[N-(p-Hydro­xy­phenyl)­amino­methyl­idene]­naphthalen-2(1H)-one propan-1-ol hemisolvate

The title compound, 2C₁₇H₁₃NO₂·C₃H₈O, adopts the keto–amine tautomeric form, with strong intramolecular N—H...O and intermolecular O—H...O hydrogen bonds which form an almost planar two-dimensional network. The asymmetric unit contains two molecules of the Schiff base and one propan-1-ol solvent molecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.136
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C21    -   C22      =       8.22 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2       =       6.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5       =       5.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19      =       6.84 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C23    -   C24      =       5.27 su
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C35    -   C36      =       1.38 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C36    -   C37      =       1.38 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C3 H8 O

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-[N-(p-Hydroxyphenyl)aminomethylidene]naphthalen-2(1H)-one–propan-1-ol (2/1)

Crystal data

2C17H13NO2·C3H8O	F(000) = 1240
Mr = 586.66	Dx = 1.292 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11900 reflections
a = 17.2090 (17) Å	θ = 4.1–29.1°
b = 8.9038 (6) Å	µ = 0.09 mm^−1
c = 19.9334 (19) Å	T = 293 K
β = 99.084 (8)°	Rectangular, orange
V = 3016.0 (5) Å^3	0.55 × 0.32 × 0.15 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	3578 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.053
Plane graphite monochromator	θmax = 27.5°, θmin = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −21→22
rotation method scans	k = −11→11
24465 measured reflections	l = −25→25
6928 independent 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0779P)^2] where P = (Fo^2 + 2Fc^2)/3
6928 reflections	(Δ/σ)max = 0.009
405 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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
C1	0.67533 (9)	1.0193 (2)	0.59055 (7)	0.0526 (4)
C2	0.62399 (10)	0.9100 (2)	0.61182 (8)	0.0583 (5)
C3	0.63343 (11)	0.8714 (2)	0.68231 (8)	0.0685 (5)
H3	0.6002	0.8005	0.6971	0.082*
C4	0.68972 (11)	0.9361 (2)	0.72738 (8)	0.0672 (5)
H4	0.6955	0.9059	0.7726	0.081*
C5	0.74084 (10)	1.0489 (2)	0.70887 (8)	0.0569 (5)
C6	0.79758 (11)	1.1171 (2)	0.75801 (9)	0.0674 (5)
H6	0.8023	1.0864	0.8031	0.081*
C7	0.84578 (12)	1.2273 (3)	0.74091 (10)	0.0763 (6)
H7	0.8833	1.2711	0.7738	0.092*
C8	0.83793 (11)	1.2730 (2)	0.67360 (9)	0.0716 (5)
H8	0.8699	1.3494	0.6616	0.086*
C9	0.78395 (10)	1.2077 (2)	0.62469 (9)	0.0636 (5)
H9	0.7805	1.2396	0.5799	0.076*
C10	0.73342 (9)	1.0931 (2)	0.64045 (7)	0.0533 (4)
C11	0.67082 (10)	1.0504 (2)	0.52124 (8)	0.0550 (4)
H11	0.7062	1.1196	0.5083	0.066*
C12	0.61273 (9)	1.0104 (2)	0.40235 (7)	0.0520 (4)
C13	0.65882 (10)	1.1119 (2)	0.37356 (8)	0.0637 (5)
H13	0.6962	1.1696	0.4010	0.076*
C14	0.64889 (11)	1.1266 (2)	0.30405 (8)	0.0685 (5)
H14	0.6795	1.1953	0.2847	0.082*
C15	0.59466 (10)	1.0417 (2)	0.26296 (8)	0.0622 (5)
C16	0.54770 (10)	0.9413 (2)	0.29127 (8)	0.0636 (5)
H16	0.5102	0.8842	0.2637	0.076*
C17	0.55729 (10)	0.9271 (2)	0.36117 (8)	0.0599 (5)
H17	0.5258	0.8602	0.3806	0.072*
C18	0.16737 (10)	0.2764 (2)	0.34860 (8)	0.0561 (4)
C19	0.12432 (10)	0.1774 (2)	0.38554 (9)	0.0629 (5)
C20	0.06324 (11)	0.0885 (2)	0.34883 (10)	0.0725 (5)
H20	0.0351	0.0231	0.3723	0.087*
C21	0.04556 (11)	0.0972 (2)	0.28097 (10)	0.0743 (6)
H21	0.0053	0.0372	0.2587	0.089*
C22	0.08607 (10)	0.1949 (2)	0.24159 (9)	0.0623 (5)
C23	0.06750 (12)	0.1988 (3)	0.17071 (10)	0.0778 (6)
H23	0.0270	0.1384	0.1491	0.093*
C24	0.10748 (13)	0.2893 (3)	0.13253 (10)	0.0833 (6)
H24	0.0944	0.2913	0.0855	0.100*
C25	0.16773 (12)	0.3779 (3)	0.16524 (9)	0.0810 (6)
H25	0.1954	0.4397	0.1397	0.097*
C26	0.18750 (11)	0.3763 (2)	0.23452 (9)	0.0712 (5)
H26	0.2283	0.4372	0.2552	0.085*
C27	0.14725 (10)	0.2843 (2)	0.27504 (8)	0.0581 (4)
C28	0.23024 (10)	0.3591 (2)	0.38321 (8)	0.0595 (5)
H28	0.2588	0.4204	0.3582	0.071*
C29	0.31331 (10)	0.4311 (2)	0.48966 (8)	0.0549 (4)
C30	0.35871 (10)	0.5387 (2)	0.46429 (8)	0.0565 (4)
H30	0.3486	0.5641	0.4185	0.068*
C31	0.41886 (10)	0.6084 (2)	0.50664 (7)	0.0559 (4)
H31	0.4493	0.6805	0.4891	0.067*
C32	0.43452 (10)	0.5725 (2)	0.57472 (7)	0.0547 (4)
C33	0.38919 (11)	0.4661 (2)	0.59993 (8)	0.0671 (5)
H33	0.3993	0.4412	0.6458	0.081*
C34	0.32875 (11)	0.3956 (2)	0.55798 (8)	0.0684 (5)
H34	0.2983	0.3241	0.5757	0.082*
C35	0.08239 (17)	−0.1658 (4)	0.52328 (19)	0.1467 (12)
H35A	0.0538	−0.0999	0.5495	0.176*
H35B	0.0537	−0.1684	0.4773	0.176*
C36	0.0816 (2)	−0.3090 (5)	0.5503 (2)	0.1750 (15)
H36A	0.1002	−0.3016	0.5987	0.210*
H36B	0.0273	−0.3420	0.5448	0.210*
C37	0.1244 (2)	−0.4203 (4)	0.5249 (2)	0.1963 (18)
H37A	0.1216	−0.5108	0.5506	0.294*
H37B	0.1783	−0.3892	0.5283	0.294*
H37C	0.1031	−0.4384	0.4782	0.294*
N1	0.61991 (9)	0.98824 (18)	0.47341 (6)	0.0564 (4)
N2	0.25101 (9)	0.35406 (18)	0.44982 (7)	0.0615 (4)
O1	0.57020 (7)	0.84410 (15)	0.56913 (5)	0.0697 (4)
O2	0.58957 (8)	1.06101 (18)	0.19434 (5)	0.0899 (5)
H22	0.5555	1.0052	0.1745	0.135*
O3	0.14070 (8)	0.16518 (16)	0.45084 (6)	0.0796 (4)
O4	0.49403 (7)	0.63595 (15)	0.61821 (5)	0.0679 (4)
H44	0.5169	0.6975	0.5977	0.102*
O5	0.15656 (9)	−0.10154 (18)	0.52116 (7)	0.0915 (4)
H55	0.1509	−0.0173	0.5044	0.137*
H1	0.5862 (11)	0.916 (2)	0.4887 (9)	0.088 (7)*
H2	0.2183 (11)	0.281 (2)	0.4685 (9)	0.092 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0538 (10)	0.0586 (12)	0.0456 (9)	0.0034 (9)	0.0091 (8)	−0.0033 (8)
C2	0.0556 (10)	0.0706 (13)	0.0486 (9)	0.0016 (10)	0.0079 (8)	−0.0091 (9)
C3	0.0688 (12)	0.0876 (15)	0.0511 (10)	−0.0080 (11)	0.0156 (9)	0.0000 (10)
C4	0.0696 (12)	0.0906 (15)	0.0419 (9)	0.0080 (12)	0.0107 (9)	−0.0023 (10)
C5	0.0557 (10)	0.0665 (13)	0.0482 (9)	0.0112 (10)	0.0070 (8)	−0.0108 (9)
C6	0.0672 (12)	0.0832 (15)	0.0499 (10)	0.0132 (11)	0.0033 (9)	−0.0125 (10)
C7	0.0685 (13)	0.0852 (16)	0.0705 (13)	0.0061 (12)	−0.0041 (10)	−0.0215 (11)
C8	0.0657 (12)	0.0714 (14)	0.0746 (13)	−0.0021 (11)	0.0009 (10)	−0.0117 (11)
C9	0.0641 (11)	0.0661 (13)	0.0590 (10)	0.0010 (10)	0.0048 (9)	−0.0031 (10)
C10	0.0532 (10)	0.0585 (12)	0.0478 (9)	0.0100 (9)	0.0064 (8)	−0.0082 (8)
C11	0.0560 (10)	0.0600 (12)	0.0485 (9)	0.0037 (9)	0.0067 (8)	−0.0027 (8)
C12	0.0528 (10)	0.0596 (12)	0.0425 (9)	0.0013 (9)	0.0046 (8)	−0.0013 (8)
C13	0.0648 (11)	0.0724 (13)	0.0523 (10)	−0.0107 (10)	0.0039 (8)	−0.0031 (9)
C14	0.0721 (12)	0.0796 (14)	0.0540 (10)	−0.0191 (11)	0.0102 (9)	0.0032 (10)
C15	0.0658 (11)	0.0771 (14)	0.0432 (9)	−0.0028 (10)	0.0070 (8)	0.0005 (9)
C16	0.0605 (11)	0.0769 (14)	0.0511 (10)	−0.0094 (10)	0.0023 (8)	−0.0080 (9)
C17	0.0589 (10)	0.0711 (13)	0.0500 (9)	−0.0077 (10)	0.0091 (8)	−0.0026 (9)
C18	0.0566 (11)	0.0522 (11)	0.0602 (10)	−0.0004 (9)	0.0114 (8)	−0.0044 (9)
C19	0.0615 (11)	0.0652 (13)	0.0632 (11)	−0.0007 (10)	0.0131 (9)	−0.0105 (10)
C20	0.0637 (12)	0.0740 (14)	0.0828 (13)	−0.0102 (11)	0.0208 (10)	−0.0082 (11)
C21	0.0579 (11)	0.0728 (15)	0.0898 (14)	−0.0032 (11)	0.0047 (10)	−0.0152 (12)
C22	0.0554 (10)	0.0592 (12)	0.0703 (12)	0.0046 (10)	0.0032 (9)	−0.0064 (10)
C23	0.0707 (13)	0.0801 (15)	0.0748 (13)	0.0038 (12)	−0.0126 (10)	−0.0125 (12)
C24	0.0943 (15)	0.0890 (16)	0.0602 (11)	0.0039 (14)	−0.0072 (11)	0.0032 (12)
C25	0.0905 (15)	0.0829 (16)	0.0654 (12)	−0.0086 (13)	−0.0008 (11)	0.0047 (11)
C26	0.0786 (13)	0.0704 (14)	0.0615 (11)	−0.0080 (11)	0.0015 (10)	−0.0008 (10)
C27	0.0558 (10)	0.0534 (11)	0.0637 (11)	0.0041 (9)	0.0051 (9)	−0.0063 (9)
C28	0.0627 (11)	0.0577 (12)	0.0584 (11)	0.0005 (10)	0.0110 (8)	−0.0044 (9)
C29	0.0582 (10)	0.0575 (12)	0.0491 (9)	−0.0007 (9)	0.0090 (8)	−0.0053 (9)
C30	0.0618 (11)	0.0630 (12)	0.0447 (8)	0.0020 (10)	0.0088 (8)	0.0033 (9)
C31	0.0574 (10)	0.0617 (12)	0.0493 (9)	−0.0027 (9)	0.0106 (8)	0.0045 (9)
C32	0.0557 (10)	0.0624 (12)	0.0459 (9)	−0.0013 (9)	0.0079 (8)	0.0010 (8)
C33	0.0740 (12)	0.0828 (15)	0.0444 (9)	−0.0090 (11)	0.0089 (9)	0.0074 (9)
C34	0.0781 (13)	0.0749 (14)	0.0539 (10)	−0.0138 (11)	0.0156 (9)	0.0082 (10)
C35	0.113 (2)	0.108 (3)	0.239 (4)	0.0142 (19)	0.087 (2)	0.038 (2)
C36	0.174 (3)	0.135 (3)	0.239 (4)	0.026 (3)	0.107 (3)	0.028 (3)
C37	0.241 (4)	0.104 (3)	0.282 (5)	0.034 (3)	0.162 (4)	0.030 (3)
N1	0.0581 (9)	0.0659 (11)	0.0448 (8)	−0.0036 (8)	0.0067 (7)	−0.0021 (7)
N2	0.0671 (10)	0.0650 (11)	0.0530 (9)	−0.0077 (9)	0.0115 (8)	−0.0054 (8)
O1	0.0691 (8)	0.0891 (10)	0.0511 (6)	−0.0193 (7)	0.0098 (6)	−0.0038 (6)
O2	0.1062 (11)	0.1173 (12)	0.0453 (7)	−0.0290 (9)	0.0088 (6)	0.0045 (7)
O3	0.0896 (9)	0.0871 (11)	0.0657 (8)	−0.0205 (8)	0.0237 (7)	−0.0054 (7)
O4	0.0675 (7)	0.0861 (10)	0.0483 (6)	−0.0126 (7)	0.0031 (6)	0.0042 (6)
O5	0.0898 (10)	0.0994 (12)	0.0870 (9)	−0.0037 (9)	0.0190 (8)	0.0011 (8)

Geometric parameters (Å, º)

C1—C11	1.399 (2)	C21—H21	0.9300
C1—C2	1.423 (2)	C22—C23	1.399 (2)
C1—C10	1.451 (2)	C22—C27	1.402 (2)
C2—O1	1.2950 (19)	C23—C24	1.367 (3)
C2—C3	1.431 (2)	C23—H23	0.9300
C3—C4	1.343 (2)	C24—C25	1.381 (3)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.422 (3)	C25—C26	1.369 (2)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.407 (2)	C26—C27	1.407 (2)
C5—C10	1.406 (2)	C26—H26	0.9300
C6—C7	1.362 (3)	C28—N2	1.320 (2)
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.388 (3)	C29—C34	1.382 (2)
C7—H7	0.9300	C29—C30	1.382 (2)
C8—C9	1.366 (2)	C29—N2	1.408 (2)
C8—H8	0.9300	C30—C31	1.376 (2)
C9—C10	1.408 (2)	C30—H30	0.9300
C9—H9	0.9300	C31—C32	1.379 (2)
C11—N1	1.311 (2)	C31—H31	0.9300
C11—H11	0.9300	C32—O4	1.3561 (18)
C12—C17	1.374 (2)	C32—C33	1.372 (2)
C12—C13	1.386 (2)	C33—C34	1.378 (2)
C12—N1	1.416 (2)	C33—H33	0.9300
C13—C14	1.375 (2)	C34—H34	0.9300
C13—H13	0.9300	C35—C36	1.385 (4)
C14—C15	1.368 (2)	C35—O5	1.405 (3)
C14—H14	0.9300	C35—H35A	0.9700
C15—O2	1.3676 (18)	C35—H35B	0.9700
C15—C16	1.383 (2)	C36—C37	1.377 (4)
C16—C17	1.383 (2)	C36—H36A	0.9700
C16—H16	0.9300	C36—H36B	0.9700
C17—H17	0.9300	C37—H37A	0.9600
C18—C28	1.397 (2)	C37—H37B	0.9600
C18—C19	1.429 (2)	C37—H37C	0.9600
C18—C27	1.454 (2)	N1—H1	0.95 (2)
C19—O3	1.292 (2)	N2—H2	0.97 (2)
C19—C20	1.422 (2)	O2—H22	0.8200
C20—C21	1.341 (2)	O4—H44	0.8200
C20—H20	0.9300	O5—H55	0.8200
C21—C22	1.425 (3)
C11—C1—C2	119.30 (15)	C27—C22—C21	118.72 (16)
C11—C1—C10	120.79 (16)	C24—C23—C22	121.49 (19)
C2—C1—C10	119.87 (14)	C24—C23—H23	119.3
O1—C2—C1	121.81 (14)	C22—C23—H23	119.3
O1—C2—C3	119.66 (17)	C23—C24—C25	118.69 (18)
C1—C2—C3	118.53 (16)	C23—C24—H24	120.7
C4—C3—C2	120.79 (18)	C25—C24—H24	120.7
C4—C3—H3	119.6	C26—C25—C24	121.2 (2)
C2—C3—H3	119.6	C26—C25—H25	119.4
C3—C4—C5	122.69 (16)	C24—C25—H25	119.4
C3—C4—H4	118.7	C25—C26—C27	121.23 (19)
C5—C4—H4	118.7	C25—C26—H26	119.4
C6—C5—C10	120.08 (19)	C27—C26—H26	119.4
C6—C5—C4	120.94 (16)	C22—C27—C26	117.28 (16)
C10—C5—C4	118.98 (16)	C22—C27—C18	119.57 (17)
C7—C6—C5	121.32 (18)	C26—C27—C18	123.13 (16)
C7—C6—H6	119.3	N2—C28—C18	122.99 (17)
C5—C6—H6	119.3	N2—C28—H28	118.5
C6—C7—C8	118.87 (18)	C18—C28—H28	118.5
C6—C7—H7	120.6	C34—C29—C30	119.14 (16)
C8—C7—H7	120.6	C34—C29—N2	117.10 (17)
C9—C8—C7	121.1 (2)	C30—C29—N2	123.76 (15)
C9—C8—H8	119.5	C31—C30—C29	120.16 (15)
C7—C8—H8	119.5	C31—C30—H30	119.9
C8—C9—C10	121.59 (17)	C29—C30—H30	119.9
C8—C9—H9	119.2	C30—C31—C32	120.70 (17)
C10—C9—H9	119.2	C30—C31—H31	119.6
C5—C10—C9	117.05 (16)	C32—C31—H31	119.6
C5—C10—C1	119.04 (17)	O4—C32—C33	117.98 (14)
C9—C10—C1	123.92 (15)	O4—C32—C31	122.91 (16)
N1—C11—C1	124.12 (17)	C33—C32—C31	119.10 (16)
N1—C11—H11	117.9	C32—C33—C34	120.69 (15)
C1—C11—H11	117.9	C32—C33—H33	119.7
C17—C12—C13	119.60 (14)	C34—C33—H33	119.7
C17—C12—N1	117.72 (16)	C33—C34—C29	120.21 (18)
C13—C12—N1	122.67 (16)	C33—C34—H34	119.9
C14—C13—C12	119.41 (17)	C29—C34—H34	119.9
C14—C13—H13	120.3	C36—C35—O5	116.8 (3)
C12—C13—H13	120.3	C36—C35—H35A	108.1
C15—C14—C13	121.00 (18)	O5—C35—H35A	108.1
C15—C14—H14	119.5	C36—C35—H35B	108.1
C13—C14—H14	119.5	O5—C35—H35B	108.1
O2—C15—C14	117.33 (17)	H35A—C35—H35B	107.3
O2—C15—C16	122.68 (16)	C37—C36—C35	118.8 (3)
C14—C15—C16	120.00 (15)	C37—C36—H36A	107.6
C17—C16—C15	119.06 (17)	C35—C36—H36A	107.6
C17—C16—H16	120.5	C37—C36—H36B	107.6
C15—C16—H16	120.5	C35—C36—H36B	107.6
C12—C17—C16	120.91 (17)	H36A—C36—H36B	107.1
C12—C17—H17	119.5	C36—C37—H37A	109.5
C16—C17—H17	119.5	C36—C37—H37B	109.5
C28—C18—C19	119.65 (16)	H37A—C37—H37B	109.5
C28—C18—C27	121.00 (17)	C36—C37—H37C	109.5
C19—C18—C27	119.29 (16)	H37A—C37—H37C	109.5
O3—C19—C20	119.82 (18)	H37B—C37—H37C	109.5
O3—C19—C18	121.51 (16)	C11—N1—C12	127.69 (17)
C20—C19—C18	118.65 (17)	C11—N1—H1	115.2 (11)
C21—C20—C19	121.20 (19)	C12—N1—H1	117.0 (11)
C21—C20—H20	119.4	C28—N2—C29	127.75 (17)
C19—C20—H20	119.4	C28—N2—H2	109.0 (11)
C20—C21—C22	122.56 (19)	C29—N2—H2	123.1 (11)
C20—C21—H21	118.7	C15—O2—H22	109.5
C22—C21—H21	118.7	C32—O4—H44	109.5
C23—C22—C27	120.05 (19)	C35—O5—H55	109.5
C23—C22—C21	121.20 (18)
C11—C1—C2—O1	−3.8 (3)	O3—C19—C20—C21	−179.13 (18)
C10—C1—C2—O1	178.43 (15)	C18—C19—C20—C21	−0.4 (3)
C11—C1—C2—C3	175.30 (16)	C19—C20—C21—C22	−0.1 (3)
C10—C1—C2—C3	−2.5 (2)	C20—C21—C22—C23	178.44 (19)
O1—C2—C3—C4	178.75 (17)	C20—C21—C22—C27	0.6 (3)
C1—C2—C3—C4	−0.3 (3)	C27—C22—C23—C24	−0.5 (3)
C2—C3—C4—C5	2.2 (3)	C21—C22—C23—C24	−178.30 (19)
C3—C4—C5—C6	178.10 (18)	C22—C23—C24—C25	0.4 (3)
C3—C4—C5—C10	−1.2 (3)	C23—C24—C25—C26	−0.2 (3)
C10—C5—C6—C7	0.5 (3)	C24—C25—C26—C27	0.1 (3)
C4—C5—C6—C7	−178.73 (18)	C23—C22—C27—C26	0.4 (3)
C5—C6—C7—C8	0.4 (3)	C21—C22—C27—C26	178.25 (17)
C6—C7—C8—C9	−1.2 (3)	C23—C22—C27—C18	−178.41 (17)
C7—C8—C9—C10	0.9 (3)	C21—C22—C27—C18	−0.5 (3)
C6—C5—C10—C9	−0.8 (2)	C25—C26—C27—C22	−0.2 (3)
C4—C5—C10—C9	178.49 (16)	C25—C26—C27—C18	178.54 (18)
C6—C5—C10—C1	179.01 (16)	C28—C18—C27—C22	177.16 (16)
C4—C5—C10—C1	−1.7 (2)	C19—C18—C27—C22	0.0 (2)
C8—C9—C10—C5	0.1 (2)	C28—C18—C27—C26	−1.5 (3)
C8—C9—C10—C1	−179.69 (17)	C19—C18—C27—C26	−178.69 (17)
C11—C1—C10—C5	−174.25 (16)	C19—C18—C28—N2	−2.2 (3)
C2—C1—C10—C5	3.5 (2)	C27—C18—C28—N2	−179.31 (17)
C11—C1—C10—C9	5.5 (3)	C34—C29—C30—C31	0.5 (3)
C2—C1—C10—C9	−176.70 (16)	N2—C29—C30—C31	−179.71 (16)
C2—C1—C11—N1	2.3 (3)	C29—C30—C31—C32	−0.2 (3)
C10—C1—C11—N1	−179.95 (16)	C30—C31—C32—O4	178.71 (16)
C17—C12—C13—C14	−0.7 (3)	C30—C31—C32—C33	−0.1 (3)
N1—C12—C13—C14	179.56 (17)	O4—C32—C33—C34	−178.83 (17)
C12—C13—C14—C15	−0.5 (3)	C31—C32—C33—C34	0.0 (3)
C13—C14—C15—O2	−178.72 (18)	C32—C33—C34—C29	0.3 (3)
C13—C14—C15—C16	1.3 (3)	C30—C29—C34—C33	−0.6 (3)
O2—C15—C16—C17	179.13 (18)	N2—C29—C34—C33	179.64 (17)
C14—C15—C16—C17	−0.9 (3)	O5—C35—C36—C37	−52.6 (6)
C13—C12—C17—C16	1.1 (3)	C1—C11—N1—C12	−178.22 (17)
N1—C12—C17—C16	−179.14 (16)	C17—C12—N1—C11	176.73 (17)
C15—C16—C17—C12	−0.3 (3)	C13—C12—N1—C11	−3.5 (3)
C28—C18—C19—O3	1.9 (3)	C18—C28—N2—C29	179.43 (17)
C27—C18—C19—O3	179.14 (17)	C34—C29—N2—C28	−173.34 (18)
C28—C18—C19—C20	−176.73 (17)	C30—C29—N2—C28	6.9 (3)
C27—C18—C19—C20	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.95 (2)	1.79 (2)	2.556 (2)	136 (2)
N2—H2···O3	0.97 (2)	1.68 (2)	2.539 (2)	145 (2)
O2—H22···O4^i	0.82	1.89	2.701 (2)	168
O4—H44···O1	0.82	1.74	2.552 (2)	169
O5—H55···O3	0.82	1.94	2.749 (2)	170

Symmetry code: (i) x, −y+3/2, z−1/2.