2-[(4-Carboxy­cyclo­hexyl)methylammonio­meth­yl]-6-hydroxy­phenolate

The title Schiff base, C₁₅H₁₉NO₄, crystallizes with two mol­ecules per asymmetric unit. In the solid state, a zwitterion is observed, with a strong intra­molecular N—H...O hydrogen bond involving the NH imine H atom and the phenolate O atom. In the crystal structure, the two crystallographically independent mol­ecules are linked by O—H...O hydrogen bonds to create centrosymmetric dimers. These dimers are connected by inter­molecular C—H...O hydrogen bonds to form layers.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.118
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.39 Ratio

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-[(4-Carboxycyclohexyl)methylammoniomethyl]-6-hydroxyphenolate

Crystal data

C15H19NO4	F(000) = 1184
Mr = 277.31	Dx = 1.357 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17098 reflections
a = 9.6396 (7) Å	θ = 1.7–29.6°
b = 17.7451 (10) Å	µ = 0.10 mm^−1
c = 15.8961 (11) Å	T = 173 K
β = 93.122 (6)°	Block, yellow
V = 2715.1 (3) Å^3	0.30 × 0.15 × 0.15 mm
Z = 8

Data collection

Stoe IPDS II diffractometer	4834 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
Graphite monochromator	θmax = 29.3°, θmin = 1.7°
Detector resolution: 6.67 pixels mm^-1	h = −13→13
φ and ω scans	k = −23→24
32025 measured reflections	l = −21→21
7347 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	All H-atom parameters refined
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0622P)^2] where P = (Fo^2 + 2Fc^2)/3
7347 reflections	(Δ/σ)max = 0.001
513 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 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
O1	0.04102 (11)	0.09299 (6)	0.74956 (7)	0.0332 (3)
O2	0.41842 (13)	−0.06011 (7)	0.32198 (8)	0.0406 (4)
O3	0.37248 (14)	0.05206 (7)	0.37513 (8)	0.0426 (4)
O4	−0.03044 (12)	0.21509 (6)	0.84333 (8)	0.0342 (3)
N1	−0.00230 (14)	−0.04617 (8)	0.70976 (9)	0.0307 (4)
C1	−0.13162 (15)	0.01695 (9)	0.81075 (9)	0.0269 (4)
C2	−0.05786 (15)	0.08588 (9)	0.80135 (9)	0.0259 (4)
C3	−0.09604 (15)	0.14765 (9)	0.85134 (10)	0.0280 (4)
C4	−0.19649 (17)	0.14030 (10)	0.90865 (10)	0.0330 (5)
C5	−0.26764 (16)	0.07216 (11)	0.91705 (11)	0.0349 (5)
C6	−0.23701 (16)	0.01188 (10)	0.86897 (10)	0.0312 (5)
C7	−0.10106 (16)	−0.04675 (9)	0.76129 (10)	0.0285 (4)
C8	0.04082 (19)	−0.10813 (9)	0.65679 (11)	0.0333 (5)
C9	0.10542 (16)	−0.07644 (9)	0.57935 (10)	0.0273 (4)
C10	0.23449 (17)	−0.02989 (10)	0.60124 (10)	0.0335 (5)
C11	0.28937 (17)	0.00549 (9)	0.52264 (10)	0.0308 (4)
C12	0.32372 (16)	−0.05397 (9)	0.45854 (10)	0.0296 (4)
C13	0.1987 (2)	−0.10464 (12)	0.43857 (12)	0.0467 (6)
C14	0.1424 (2)	−0.13846 (11)	0.51848 (13)	0.0463 (6)
C15	0.37653 (15)	−0.02171 (9)	0.37822 (10)	0.0300 (4)
O21	0.45690 (10)	0.11819 (6)	0.24727 (7)	0.0298 (3)
O22	0.16239 (11)	0.26673 (6)	0.72025 (7)	0.0343 (3)
O23	0.14095 (17)	0.17038 (8)	0.63273 (9)	0.0547 (5)
O24	0.58514 (13)	−0.00453 (7)	0.18224 (9)	0.0447 (4)
N21	0.47000 (13)	0.26061 (8)	0.28740 (8)	0.0271 (3)
C21	0.64220 (15)	0.19858 (9)	0.21056 (9)	0.0265 (4)
C22	0.57518 (15)	0.12747 (8)	0.21321 (9)	0.0249 (4)
C23	0.64289 (16)	0.06506 (9)	0.17734 (10)	0.0313 (4)
C24	0.76342 (18)	0.07431 (11)	0.13741 (11)	0.0372 (5)
C25	0.82649 (18)	0.14497 (11)	0.13342 (11)	0.0386 (5)
C26	0.76917 (17)	0.20573 (10)	0.17020 (11)	0.0341 (5)
C27	0.58671 (16)	0.26219 (9)	0.25095 (9)	0.0267 (4)
C28	0.40992 (17)	0.32213 (9)	0.33439 (10)	0.0284 (4)
C29	0.34109 (15)	0.29056 (8)	0.41067 (9)	0.0252 (4)
C30	0.44234 (16)	0.25242 (9)	0.47437 (10)	0.0297 (4)
C31	0.36367 (17)	0.21629 (9)	0.54443 (10)	0.0300 (5)
C32	0.27489 (15)	0.27350 (9)	0.58878 (9)	0.0258 (4)
C33	0.17962 (15)	0.31725 (9)	0.52547 (10)	0.0275 (4)
C34	0.26038 (16)	0.35130 (9)	0.45486 (10)	0.0270 (4)
C35	0.18833 (15)	0.23727 (9)	0.65434 (9)	0.0270 (4)
H1N	0.0417 (19)	0.0022 (11)	0.7102 (12)	0.036 (5)*
H3O	0.404 (2)	0.0705 (13)	0.3232 (14)	0.054 (6)*
H4	−0.219 (2)	0.1834 (12)	0.9417 (13)	0.043 (5)*
H4O	0.024 (2)	0.2113 (13)	0.8020 (14)	0.053 (6)*
H5	−0.334 (2)	0.0678 (11)	0.9605 (12)	0.042 (5)*
H6	−0.2853 (18)	−0.0345 (11)	0.8703 (11)	0.035 (5)*
H7	−0.1511 (18)	−0.0915 (10)	0.7642 (11)	0.029 (4)*
H8A	−0.041 (2)	−0.1398 (11)	0.6400 (11)	0.039 (5)*
H8B	0.110 (2)	−0.1402 (11)	0.6900 (12)	0.041 (5)*
H9	0.0354 (18)	−0.0400 (11)	0.5511 (11)	0.034 (5)*
H10A	0.221 (2)	0.0081 (12)	0.6420 (13)	0.045 (5)*
H10B	0.310 (2)	−0.0654 (13)	0.6314 (14)	0.056 (6)*
H11A	0.2210 (18)	0.0419 (10)	0.4965 (11)	0.032 (4)*
H11B	0.368 (2)	0.0362 (12)	0.5373 (12)	0.044 (5)*
H12	0.400 (2)	−0.0869 (12)	0.4823 (13)	0.050 (6)*
H13A	0.125 (2)	−0.0737 (13)	0.4081 (13)	0.050 (6)*
H13B	0.221 (2)	−0.1430 (14)	0.4020 (14)	0.058 (6)*
H14A	0.064 (3)	−0.1691 (14)	0.5023 (15)	0.065 (7)*
H14B	0.216 (3)	−0.1736 (15)	0.5524 (16)	0.072 (8)*
H21N	0.428 (2)	0.2124 (12)	0.2825 (13)	0.044 (5)*
H23O	0.099 (3)	0.1515 (15)	0.6812 (16)	0.074 (8)*
H24	0.804 (2)	0.0304 (12)	0.1130 (13)	0.049 (6)*
H24O	0.513 (3)	−0.0001 (18)	0.2230 (19)	0.101 (10)*
H25	0.909 (2)	0.1515 (13)	0.0999 (14)	0.060 (6)*
H26	0.815 (2)	0.2562 (12)	0.1735 (12)	0.041 (5)*
H27	0.6370 (17)	0.3105 (10)	0.2539 (10)	0.028 (4)*
H28A	0.4796 (17)	0.3581 (10)	0.3505 (10)	0.024 (4)*
H28B	0.3400 (18)	0.3490 (10)	0.2948 (10)	0.028 (4)*
H29	0.2796 (17)	0.2518 (10)	0.3892 (10)	0.023 (4)*
H30A	0.5080 (19)	0.2940 (11)	0.4979 (11)	0.033 (5)*
H30B	0.4969 (18)	0.2124 (11)	0.4451 (11)	0.034 (5)*
H31A	0.3015 (18)	0.1763 (10)	0.5186 (11)	0.029 (4)*
H31B	0.4260 (18)	0.1909 (10)	0.5858 (11)	0.033 (5)*
H32	0.3332 (18)	0.3110 (10)	0.6183 (11)	0.028 (4)*
H33A	0.1079 (19)	0.2815 (10)	0.4997 (11)	0.034 (5)*
H33B	0.1310 (18)	0.3574 (10)	0.5563 (10)	0.027 (4)*
H34A	0.3259 (17)	0.3910 (10)	0.4793 (11)	0.028 (4)*
H34B	0.2002 (18)	0.3776 (10)	0.4154 (11)	0.028 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0363 (6)	0.0268 (6)	0.0377 (6)	−0.0058 (4)	0.0139 (5)	0.0002 (5)
O2	0.0506 (7)	0.0361 (7)	0.0360 (6)	0.0011 (5)	0.0116 (5)	−0.0014 (5)
O3	0.0578 (8)	0.0280 (6)	0.0439 (7)	0.0015 (5)	0.0195 (6)	0.0059 (5)
O4	0.0420 (6)	0.0232 (6)	0.0381 (6)	−0.0025 (5)	0.0081 (5)	−0.0026 (5)
N1	0.0373 (7)	0.0203 (6)	0.0352 (7)	−0.0042 (5)	0.0085 (6)	−0.0003 (5)
C1	0.0262 (7)	0.0258 (8)	0.0285 (7)	−0.0024 (6)	0.0006 (6)	0.0035 (6)
C2	0.0271 (7)	0.0252 (7)	0.0255 (7)	−0.0006 (6)	0.0018 (6)	0.0028 (6)
C3	0.0294 (7)	0.0247 (7)	0.0293 (7)	0.0015 (6)	−0.0028 (6)	0.0023 (6)
C4	0.0366 (8)	0.0316 (9)	0.0311 (8)	0.0061 (7)	0.0036 (6)	−0.0024 (7)
C5	0.0301 (8)	0.0424 (10)	0.0330 (8)	0.0027 (7)	0.0085 (7)	0.0037 (7)
C6	0.0275 (7)	0.0317 (9)	0.0347 (8)	−0.0030 (6)	0.0046 (6)	0.0062 (7)
C7	0.0307 (7)	0.0246 (8)	0.0303 (7)	−0.0036 (6)	0.0017 (6)	0.0055 (6)
C8	0.0447 (9)	0.0198 (7)	0.0363 (9)	−0.0022 (7)	0.0104 (7)	−0.0006 (7)
C9	0.0311 (7)	0.0205 (7)	0.0304 (7)	−0.0020 (6)	0.0030 (6)	0.0010 (6)
C10	0.0346 (8)	0.0351 (9)	0.0311 (8)	−0.0070 (7)	0.0038 (7)	−0.0045 (7)
C11	0.0290 (7)	0.0285 (8)	0.0350 (8)	−0.0071 (6)	0.0032 (6)	−0.0033 (7)
C12	0.0302 (7)	0.0251 (8)	0.0339 (8)	0.0042 (6)	0.0049 (6)	0.0023 (6)
C13	0.0658 (13)	0.0370 (10)	0.0391 (10)	−0.0237 (9)	0.0200 (9)	−0.0152 (9)
C14	0.0666 (13)	0.0281 (9)	0.0463 (11)	−0.0185 (9)	0.0230 (10)	−0.0092 (8)
C15	0.0261 (7)	0.0302 (8)	0.0336 (8)	−0.0001 (6)	0.0016 (6)	0.0003 (7)
O21	0.0274 (5)	0.0242 (5)	0.0384 (6)	−0.0013 (4)	0.0067 (4)	0.0024 (5)
O22	0.0367 (6)	0.0309 (6)	0.0365 (6)	−0.0033 (5)	0.0135 (5)	−0.0030 (5)
O23	0.0839 (10)	0.0414 (8)	0.0414 (7)	−0.0346 (7)	0.0271 (7)	−0.0110 (6)
O24	0.0396 (7)	0.0274 (6)	0.0680 (9)	−0.0012 (5)	0.0111 (6)	−0.0121 (6)
N21	0.0321 (6)	0.0217 (6)	0.0278 (6)	−0.0014 (5)	0.0057 (5)	0.0004 (5)
C21	0.0291 (7)	0.0265 (8)	0.0239 (7)	0.0012 (6)	0.0019 (5)	0.0044 (6)
C22	0.0263 (7)	0.0257 (7)	0.0227 (7)	0.0023 (6)	0.0006 (5)	0.0026 (6)
C23	0.0315 (7)	0.0274 (8)	0.0345 (8)	0.0030 (6)	−0.0017 (6)	−0.0023 (7)
C24	0.0372 (8)	0.0391 (10)	0.0357 (9)	0.0090 (7)	0.0063 (7)	−0.0057 (8)
C25	0.0341 (8)	0.0490 (11)	0.0339 (8)	0.0060 (7)	0.0124 (7)	0.0057 (8)
C26	0.0333 (8)	0.0340 (9)	0.0355 (8)	−0.0025 (7)	0.0076 (6)	0.0082 (7)
C27	0.0307 (7)	0.0228 (7)	0.0269 (7)	−0.0034 (6)	0.0031 (6)	0.0035 (6)
C28	0.0354 (8)	0.0189 (7)	0.0313 (8)	−0.0005 (6)	0.0054 (6)	0.0005 (6)
C29	0.0266 (7)	0.0215 (7)	0.0277 (7)	−0.0010 (6)	0.0029 (6)	−0.0009 (6)
C30	0.0284 (7)	0.0281 (8)	0.0328 (8)	0.0052 (6)	0.0049 (6)	0.0010 (6)
C31	0.0330 (8)	0.0264 (8)	0.0307 (8)	0.0038 (6)	0.0037 (6)	0.0039 (6)
C32	0.0258 (7)	0.0247 (8)	0.0269 (7)	−0.0044 (5)	0.0026 (5)	−0.0018 (6)
C33	0.0246 (7)	0.0246 (8)	0.0336 (8)	0.0000 (6)	0.0056 (6)	−0.0002 (6)
C34	0.0285 (7)	0.0204 (7)	0.0324 (8)	0.0009 (6)	0.0048 (6)	0.0007 (6)
C35	0.0277 (7)	0.0242 (7)	0.0291 (7)	−0.0023 (6)	0.0013 (6)	0.0018 (6)

Geometric parameters (Å, º)

O1—C2	1.2991 (18)	C10—H10B	1.06 (2)
O2—C15	1.211 (2)	C10—H10A	0.95 (2)
O3—C15	1.311 (2)	C11—H11A	0.997 (18)
O4—C3	1.3627 (19)	C11—H11B	0.95 (2)
O3—H3O	0.95 (2)	C12—H12	1.00 (2)
O4—H4O	0.87 (2)	C13—H13A	1.00 (2)
O21—C22	1.2990 (18)	C13—H13B	0.93 (2)
O22—C35	1.2092 (18)	C14—H14B	1.07 (3)
O23—C35	1.311 (2)	C14—H14A	0.96 (3)
O24—C23	1.359 (2)	C21—C22	1.419 (2)
O23—H23O	0.95 (3)	C21—C26	1.418 (2)
O24—H24O	0.98 (3)	C21—C27	1.418 (2)
N1—C7	1.289 (2)	C22—C23	1.421 (2)
N1—C8	1.459 (2)	C23—C24	1.364 (2)
N1—H1N	0.957 (19)	C24—C25	1.396 (3)
N21—C28	1.460 (2)	C25—C26	1.358 (3)
N21—C27	1.294 (2)	C28—C29	1.521 (2)
N21—H21N	0.95 (2)	C29—C30	1.526 (2)
C1—C2	1.427 (2)	C29—C34	1.523 (2)
C1—C6	1.414 (2)	C30—C31	1.523 (2)
C1—C7	1.417 (2)	C31—C32	1.525 (2)
C2—C3	1.414 (2)	C32—C33	1.536 (2)
C3—C4	1.371 (2)	C32—C35	1.513 (2)
C4—C5	1.400 (3)	C33—C34	1.525 (2)
C5—C6	1.357 (3)	C24—H24	0.96 (2)
C8—C9	1.518 (2)	C25—H25	0.99 (2)
C9—C10	1.518 (2)	C26—H26	1.00 (2)
C9—C14	1.521 (3)	C27—H27	0.985 (18)
C10—C11	1.519 (2)	C28—H28A	0.952 (17)
C11—C12	1.516 (2)	C28—H28B	1.016 (17)
C12—C15	1.513 (2)	C29—H29	0.959 (17)
C12—C13	1.523 (3)	C30—H30A	1.029 (19)
C13—C14	1.531 (3)	C30—H30B	1.012 (18)
C4—H4	0.96 (2)	C31—H31A	1.002 (17)
C5—H5	0.970 (19)	C31—H31B	0.976 (18)
C6—H6	0.946 (19)	C32—H32	0.975 (18)
C7—H7	0.932 (18)	C33—H33A	1.009 (18)
C8—H8A	0.993 (19)	C33—H33B	0.996 (17)
C8—H8B	1.004 (19)	C34—H34A	1.010 (17)
C9—H9	1.021 (18)	C34—H34B	0.953 (18)
O1···O4	2.7391 (16)	H1N···C2	2.319 (19)
O1···O23	2.5412 (18)	H1N···O1	1.728 (19)
O1···N1	2.5776 (18)	H1N···C10	2.670 (19)
O1···C35	3.3312 (19)	H1N···H10A	2.09 (3)
O2···C27^i	3.359 (2)	H3O···O21	1.58 (2)
O2···O24	2.9797 (19)	H3O···C22	2.67 (2)
O3···O21	2.5200 (17)	H3O···H24O	2.32 (4)
O3···C7^ii	3.307 (2)	H4···H14B^iii	2.54 (3)
O4···O1	2.7391 (16)	H4O···O22	2.15 (2)
O4···C8^iii	3.1386 (19)	H4O···C35	2.94 (2)
O4···O22	2.9187 (16)	H4O···H23O	2.34 (3)
O21···O3	2.5200 (17)	H4O···O1	2.27 (2)
O21···C15	3.3574 (19)	H5···C24^vii	2.918 (19)
O21···N21	2.6079 (18)	H6···H7	2.40 (2)
O21···O24	2.7346 (17)	H6···O21^ii	2.846 (18)
O22···C7^iii	3.3778 (19)	H7···H8A	2.45 (3)
O22···C28^iv	3.317 (2)	H7···H6	2.40 (2)
O22···N21^iv	3.1341 (17)	H7···O22^viii	2.531 (18)
O22···O4	2.9187 (16)	H8A···H7	2.45 (3)
O23···O1	2.5412 (18)	H8A···H14A	2.52 (3)
O24···C6^ii	3.412 (2)	H8A···O4^viii	2.68 (2)
O24···O21	2.7346 (17)	H8B···C25^vi	2.841 (19)
O24···C28^i	3.088 (2)	H8B···H10B	2.56 (3)
O24···O2	2.9797 (19)	H8B···H14B	2.53 (3)
O1···H23O	1.62 (3)	H8B···C26^vi	2.714 (19)
O1···H1N	1.728 (19)	H8B···C21^vi	2.978 (19)
O1···H4O	2.27 (2)	H8B···O4^viii	2.72 (2)
O1···H10A	2.92 (2)	H9···H13A	2.55 (3)
O1···H13A^ii	2.92 (2)	H9···H11A	2.50 (3)
O2···H27^i	2.635 (17)	H9···H9^ii	2.24 (3)
O2···H13B	2.77 (2)	H9···H11A^ii	2.55 (2)
O2···H24O	2.14 (3)	H10A···N1	2.64 (2)
O3···H11A	2.489 (17)	H10A···O1	2.92 (2)
O3···H11B	2.596 (19)	H10A···H1N	2.09 (3)
O4···H8B^iii	2.72 (2)	H10B···H8B	2.56 (3)
O4···H33A^iv	2.757 (18)	H10B···H12	2.60 (3)
O4···H8A^iii	2.68 (2)	H10B···C23^vi	3.05 (2)
O21···H3O	1.58 (2)	H10B···H14B	2.44 (3)
O21···H6^ii	2.846 (18)	H10B···C22^vi	2.87 (2)
O21···H24O	2.21 (3)	H11A···H9	2.50 (3)
O21···H21N	1.79 (2)	H11A···H31A	2.53 (3)
O21···H32^v	2.634 (18)	H11A···H9^ii	2.55 (2)
O22···H7^iii	2.531 (18)	H11A···O3	2.489 (17)
O22···H4O	2.15 (2)	H11B···O3	2.596 (19)
O22···H21N^iv	2.72 (2)	H11B···H12^vi	2.45 (3)
O22···H28B^iv	2.887 (17)	H11B···H31A	2.58 (3)
O22···H29^iv	2.875 (16)	H11B···C12^vi	2.986 (19)
O23···H31B	2.909 (17)	H11B···C15^vi	2.752 (19)
O23···H31A	2.450 (17)	H12···H10B	2.60 (3)
O23···H14A^ii	2.84 (3)	H12···H11B^vi	2.45 (3)
O23···H33A	2.896 (18)	H13A···H9	2.55 (3)
O24···H28A^i	2.563 (18)	H13A···O1^ii	2.92 (2)
O24···H28B^i	2.717 (18)	H13B···H26^i	2.17 (3)
N1···O1	2.5776 (18)	H13B···O2	2.77 (2)
N1···C25^vi	3.421 (2)	H13B···C26^i	2.92 (2)
N1···C24^vi	3.293 (2)	H14A···O23^ii	2.84 (3)
N21···C35^v	3.3499 (19)	H14A···H8A	2.52 (3)
N21···O21	2.6079 (18)	H14A···H33A^ii	2.59 (3)
N21···O22^v	3.1341 (17)	H14B···H4^viii	2.54 (3)
N1···H10A	2.64 (2)	H14B···H10B	2.44 (3)
N21···H30B	2.648 (18)	H14B···H8B	2.53 (3)
C4···C25^vii	3.569 (2)	H21N···O21	1.79 (2)
C5···C24^vii	3.500 (2)	H21N···C22	2.38 (2)
C6···O24^ii	3.412 (2)	H21N···H29	2.38 (3)
C7···C25^vi	3.516 (2)	H21N···O22^v	2.72 (2)
C7···C15^ii	3.578 (2)	H23O···O1	1.62 (3)
C7···O3^ii	3.307 (2)	H23O···C2	2.76 (3)
C7···C24^vi	3.585 (2)	H23O···H4O	2.34 (3)
C7···O22^viii	3.3778 (19)	H24O···O2	2.14 (3)
C8···C25^vi	3.567 (2)	H24O···O21	2.21 (3)
C8···O4^viii	3.1386 (19)	H24O···C15	2.88 (3)
C11···C15^vi	3.519 (2)	H24O···H3O	2.32 (4)
C15···C7^ii	3.578 (2)	H24O···C6^ii	2.97 (3)
C15···O21	3.3574 (19)	H25···C33^xii	2.98 (2)
C15···C11^vi	3.519 (2)	H25···H33B^xii	2.29 (3)
C24···N1^vi	3.293 (2)	H26···H27	2.40 (3)
C24···C7^vi	3.585 (2)	H26···C13^x	3.04 (2)
C24···C5^ix	3.500 (2)	H26···H13B^x	2.17 (3)
C25···C7^vi	3.516 (2)	H27···H26	2.40 (3)
C25···C4^ix	3.569 (2)	H27···H28A	2.37 (2)
C25···N1^vi	3.421 (2)	H27···O2^x	2.635 (17)
C25···C8^vi	3.567 (2)	H27···C3^xii	3.023 (16)
C27···O2^x	3.359 (2)	H27···C4^xii	2.993 (16)
C28···O22^v	3.317 (2)	H28A···H27	2.37 (2)
C28···O24^x	3.088 (2)	H28A···O24^x	2.563 (18)
C35···N21^iv	3.3499 (19)	H28A···C5^xii	2.882 (17)
C35···O1	3.3312 (19)	H28B···H34B	2.46 (2)
C2···H23O	2.76 (3)	H28B···O24^x	2.717 (18)
C2···H34B^iv	3.067 (18)	H28B···O22^v	2.887 (17)
C2···H1N	2.319 (19)	H28B···C35^v	3.018 (17)
C3···H34B^iv	3.013 (17)	H29···H21N	2.38 (3)
C3···H27^xi	3.023 (16)	H29···H31A	2.45 (2)
C4···H27^xi	2.993 (16)	H29···H33A	2.53 (2)
C5···H28A^xi	2.882 (17)	H29···O22^v	2.875 (16)
C6···H24O^ii	2.97 (3)	H30A···H34A	2.47 (3)
C10···H1N	2.670 (19)	H30B···N21	2.648 (18)
C11···H31A	3.034 (18)	H31A···O23	2.450 (17)
C12···H11B^vi	2.986 (19)	H31A···C11	3.034 (18)
C13···H26^i	3.04 (2)	H31A···H11A	2.53 (3)
C15···H11B^vi	2.752 (19)	H31A···H11B	2.58 (3)
C15···H24O	2.88 (3)	H31A···H29	2.45 (2)
C21···H8B^vi	2.978 (19)	H31B···O23	2.909 (17)
C22···H10B^vi	2.87 (2)	H31B···C27^iv	3.089 (17)
C22···H3O	2.67 (2)	H32···O21^iv	2.634 (17)
C22···H21N	2.38 (2)	H32···C22^iv	2.920 (17)
C22···H32^v	2.920 (17)	H33A···O23	2.896 (18)
C23···H10B^vi	3.05 (2)	H33A···H29	2.53 (2)
C24···H5^ix	2.918 (19)	H33A···H14A^ii	2.59 (3)
C25···H8B^vi	2.841 (19)	H33A···O4^v	2.757 (18)
C26···H13B^x	2.92 (2)	H33B···H25^xi	2.29 (3)
C26···H8B^vi	2.714 (19)	H34A···H30A	2.47 (3)
C27···H31B^v	3.089 (18)	H34B···H28B	2.46 (2)
C33···H25^xi	2.98 (2)	H34B···C2^v	3.067 (18)
C35···H4O	2.94 (2)	H34B···C3^v	3.013 (17)
C35···H28B^iv	3.018 (17)
C15—O3—H3O	111.4 (14)	C9—C14—H14B	105.9 (14)
C3—O4—H4O	107.8 (15)	C9—C14—H14A	112.0 (16)
C35—O23—H23O	105.3 (16)	H14A—C14—H14B	107 (2)
C23—O24—H24O	105.8 (19)	C13—C14—H14A	108.1 (15)
C7—N1—C8	127.16 (14)	C13—C14—H14B	113.1 (15)
C7—N1—H1N	110.2 (11)	C22—C21—C27	120.72 (13)
C8—N1—H1N	122.7 (11)	C26—C21—C27	119.33 (14)
C27—N21—C28	126.28 (14)	C22—C21—C26	119.90 (14)
C28—N21—H21N	122.5 (12)	O21—C22—C21	122.44 (13)
C27—N21—H21N	111.2 (12)	O21—C22—C23	120.09 (13)
C6—C1—C7	119.40 (14)	C21—C22—C23	117.47 (13)
C2—C1—C6	120.20 (14)	O24—C23—C22	119.14 (14)
C2—C1—C7	120.39 (13)	O24—C23—C24	119.88 (15)
O1—C2—C1	122.46 (14)	C22—C23—C24	120.97 (15)
O1—C2—C3	120.21 (14)	C23—C24—C25	120.88 (17)
C1—C2—C3	117.33 (13)	C24—C25—C26	120.32 (16)
C2—C3—C4	120.95 (15)	C21—C26—C25	120.34 (16)
O4—C3—C2	119.46 (13)	N21—C27—C21	122.99 (15)
O4—C3—C4	119.58 (15)	N21—C28—C29	109.57 (13)
C3—C4—C5	120.85 (16)	C30—C29—C34	109.40 (12)
C4—C5—C6	120.30 (15)	C28—C29—C30	113.67 (12)
C1—C6—C5	120.32 (16)	C28—C29—C34	111.29 (12)
N1—C7—C1	121.95 (15)	C29—C30—C31	110.25 (13)
N1—C8—C9	109.35 (13)	C30—C31—C32	111.85 (13)
C10—C9—C14	108.79 (14)	C31—C32—C33	111.36 (12)
C8—C9—C14	111.64 (14)	C31—C32—C35	112.33 (13)
C8—C9—C10	112.53 (13)	C33—C32—C35	109.49 (12)
C9—C10—C11	110.75 (13)	C32—C33—C34	111.81 (12)
C10—C11—C12	111.34 (13)	C29—C34—C33	110.68 (13)
C11—C12—C13	110.59 (14)	O22—C35—C32	124.11 (14)
C11—C12—C15	113.57 (13)	O23—C35—C32	113.67 (13)
C13—C12—C15	110.26 (13)	O22—C35—O23	122.21 (14)
C12—C13—C14	111.76 (15)	C23—C24—H24	117.7 (12)
C9—C14—C13	110.50 (16)	C25—C24—H24	121.4 (12)
O3—C15—C12	113.52 (14)	C24—C25—H25	119.7 (13)
O2—C15—C12	123.46 (15)	C26—C25—H25	119.8 (13)
O2—C15—O3	123.02 (15)	C21—C26—H26	116.5 (11)
C5—C4—H4	120.6 (12)	C25—C26—H26	123.0 (11)
C3—C4—H4	118.5 (12)	N21—C27—H27	115.8 (10)
C6—C5—H5	120.7 (12)	C21—C27—H27	121.2 (10)
C4—C5—H5	118.8 (12)	N21—C28—H28A	110.2 (10)
C5—C6—H6	123.4 (11)	N21—C28—H28B	107.6 (10)
C1—C6—H6	116.2 (11)	C29—C28—H28A	111.4 (10)
N1—C7—H7	116.1 (11)	C29—C28—H28B	111.3 (10)
C1—C7—H7	121.9 (11)	H28A—C28—H28B	106.7 (14)
C9—C8—H8A	110.3 (10)	C28—C29—H29	105.6 (10)
C9—C8—H8B	110.3 (11)	C30—C29—H29	106.2 (10)
H8A—C8—H8B	108.4 (16)	C34—C29—H29	110.5 (10)
N1—C8—H8B	109.0 (11)	C29—C30—H30A	106.4 (10)
N1—C8—H8A	109.5 (11)	C29—C30—H30B	109.6 (10)
C8—C9—H9	107.5 (10)	C31—C30—H30A	110.9 (10)
C14—C9—H9	110.5 (10)	C31—C30—H30B	109.4 (11)
C10—C9—H9	105.7 (10)	H30A—C30—H30B	110.2 (14)
H10A—C10—H10B	103.3 (17)	C30—C31—H31A	108.0 (10)
C11—C10—H10B	110.9 (11)	C30—C31—H31B	112.0 (10)
C9—C10—H10A	113.7 (12)	C32—C31—H31A	108.8 (10)
C9—C10—H10B	108.4 (12)	C32—C31—H31B	109.6 (10)
C11—C10—H10A	109.6 (12)	H31A—C31—H31B	106.4 (15)
H11A—C11—H11B	103.3 (16)	C31—C32—H32	110.7 (10)
C10—C11—H11B	110.1 (12)	C33—C32—H32	106.2 (10)
C12—C11—H11A	109.5 (10)	C35—C32—H32	106.5 (10)
C10—C11—H11A	111.0 (10)	C32—C33—H33A	108.7 (10)
C12—C11—H11B	111.3 (12)	C32—C33—H33B	108.7 (9)
C13—C12—H12	107.0 (12)	C34—C33—H33A	108.4 (10)
C15—C12—H12	105.5 (12)	C34—C33—H33B	110.6 (10)
C11—C12—H12	109.7 (12)	H33A—C33—H33B	108.6 (14)
C12—C13—H13B	110.9 (13)	C29—C34—H34A	110.3 (10)
C14—C13—H13A	110.0 (12)	C29—C34—H34B	110.5 (11)
C12—C13—H13A	108.0 (13)	C33—C34—H34A	109.1 (10)
H13A—C13—H13B	106.4 (18)	C33—C34—H34B	111.2 (11)
C14—C13—H13B	109.7 (15)	H34A—C34—H34B	104.9 (14)
C8—N1—C7—C1	178.82 (15)	C15—C12—C13—C14	179.93 (14)
C7—N1—C8—C9	152.67 (16)	C12—C13—C14—C9	56.6 (2)
C28—N21—C27—C21	176.19 (14)	C26—C21—C22—O21	−178.05 (14)
C27—N21—C28—C29	−141.56 (15)	C26—C21—C22—C23	2.4 (2)
C6—C1—C2—O1	179.04 (14)	C27—C21—C22—O21	4.6 (2)
C7—C1—C2—C3	178.55 (14)	C27—C21—C22—C23	−174.91 (14)
C2—C1—C6—C5	−0.8 (2)	C22—C21—C26—C25	0.5 (2)
C7—C1—C6—C5	179.85 (15)	C27—C21—C26—C25	177.91 (15)
C2—C1—C7—N1	3.5 (2)	C22—C21—C27—N21	−4.3 (2)
C6—C1—C7—N1	−177.14 (15)	C26—C21—C27—N21	178.37 (15)
C7—C1—C2—O1	−1.6 (2)	O21—C22—C23—O24	−2.6 (2)
C6—C1—C2—C3	−0.8 (2)	O21—C22—C23—C24	176.55 (15)
O1—C2—C3—C4	−177.47 (14)	C21—C22—C23—O24	176.92 (14)
O1—C2—C3—O4	1.5 (2)	C21—C22—C23—C24	−3.9 (2)
C1—C2—C3—C4	2.4 (2)	O24—C23—C24—C25	−178.40 (16)
C1—C2—C3—O4	−178.69 (13)	C22—C23—C24—C25	2.4 (3)
C2—C3—C4—C5	−2.4 (2)	C23—C24—C25—C26	0.7 (3)
O4—C3—C4—C5	178.68 (15)	C24—C25—C26—C21	−2.2 (3)
C3—C4—C5—C6	0.7 (3)	N21—C28—C29—C30	63.59 (16)
C4—C5—C6—C1	0.9 (2)	N21—C28—C29—C34	−172.35 (12)
N1—C8—C9—C10	61.67 (18)	C28—C29—C30—C31	−174.86 (13)
N1—C8—C9—C14	−175.67 (14)	C34—C29—C30—C31	60.07 (16)
C8—C9—C14—C13	176.41 (15)	C28—C29—C34—C33	174.04 (12)
C10—C9—C14—C13	−58.82 (19)	C30—C29—C34—C33	−59.52 (16)
C14—C9—C10—C11	60.01 (18)	C29—C30—C31—C32	−57.17 (17)
C8—C9—C10—C11	−175.74 (13)	C30—C31—C32—C33	52.70 (17)
C9—C10—C11—C12	−58.48 (18)	C30—C31—C32—C35	175.91 (12)
C10—C11—C12—C15	178.98 (13)	C31—C32—C33—C34	−51.89 (17)
C10—C11—C12—C13	54.40 (18)	C35—C32—C33—C34	−176.72 (13)
C11—C12—C15—O2	174.73 (15)	C31—C32—C35—O22	144.44 (15)
C11—C12—C15—O3	−5.37 (19)	C31—C32—C35—O23	−36.60 (18)
C13—C12—C15—O2	−60.5 (2)	C33—C32—C35—O22	−91.30 (17)
C13—C12—C15—O3	119.38 (16)	C33—C32—C35—O23	87.66 (16)
C11—C12—C13—C14	−53.6 (2)	C32—C33—C34—C29	55.74 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.957 (19)	1.728 (19)	2.5776 (18)	145.9 (17)
O3—H3O···O21	0.95 (2)	1.58 (2)	2.5200 (17)	168 (2)
O4—H4O···O1	0.87 (2)	2.27 (2)	2.7391 (16)	114.2 (18)
O4—H4O···O22	0.87 (2)	2.15 (2)	2.9187 (16)	148 (2)
N21—H21N···O21	0.95 (2)	1.79 (2)	2.6079 (18)	142.7 (17)
O23—H23O···O1	0.95 (3)	1.62 (3)	2.5412 (18)	161 (2)
O24—H24O···O2	0.98 (3)	2.14 (3)	2.9797 (19)	142 (3)
O24—H24O···O21	0.98 (3)	2.21 (3)	2.7346 (17)	112 (2)
C7—H7···O22^viii	0.932 (18)	2.531 (18)	3.3778 (19)	151.3 (14)
C28—H28A···O24^x	0.952 (17)	2.563 (18)	3.088 (2)	115.0 (12)

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