2-Hydr­oxy-6-[(m-tolyl­iminio)meth­yl]phenolate

In the solid state, the title compound, C₁₄H₁₃NO₂, crystallizes as a zwitterion. Two mol­ecules comprise the asymmetric unit. The mol­ecules exhibit two types of hydrogen bonds: N—H...O hydrogen bonds involving hydr­oxy and imine groups generate an S(6) ring motif, and O—H...O hydrogen bonds linking two symmetry-related mol­ecules form a centrosymmetric dimer.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.127
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O11
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O21
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2007) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2-Hydroxy-6-[(m-tolyliminio)methyl]phenolate

Crystal data

C14H13NO2	Z = 4
Mr = 227.25	F(000) = 480
Triclinic, P1	The final unit cell was obtained from the xyz centroids of 2168 reflections after integration using the SAINT-Plus software package (Bruker, 2000). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Hall symbol: -P 1	Dx = 1.360 Mg m^−3
a = 7.7094 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5939 (9) Å	Cell parameters from 2168 reflections
c = 14.8307 (13) Å	θ = 2.8–27.3°
α = 72.2740 (15)°	µ = 0.09 mm^−1
β = 83.0670 (16)°	T = 100 K
γ = 74.2580 (15)°	Block, red
V = 1109.52 (17) Å^3	0.39 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4253 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2951 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.027
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.0°, θmin = 2.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −12→13
Tmin = 0.955, Tmax = 0.989	l = −18→18
7014 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
4253 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.21 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
O11	−0.30956 (17)	0.46121 (13)	0.44824 (10)	0.0294 (4)
O12	−0.61344 (18)	0.62343 (14)	0.35839 (11)	0.0319 (5)
N1	0.0301 (2)	0.37546 (15)	0.44598 (11)	0.0229 (5)
C11	−0.2912 (3)	0.54424 (18)	0.36417 (13)	0.0233 (6)
C12	−0.4475 (3)	0.63121 (19)	0.31473 (14)	0.0249 (6)
C13	−0.4334 (3)	0.71750 (19)	0.22577 (14)	0.0262 (6)
C14	−0.2624 (3)	0.72581 (19)	0.18151 (14)	0.0286 (6)
C15	−0.1079 (3)	0.64563 (19)	0.22702 (13)	0.0269 (6)
C16	−0.1193 (3)	0.55269 (18)	0.31780 (13)	0.0234 (6)
C17	0.0402 (3)	0.46546 (19)	0.36446 (13)	0.0233 (6)
C18	0.1736 (3)	0.27812 (18)	0.49996 (13)	0.0220 (6)
C19	0.3529 (3)	0.25659 (19)	0.46668 (13)	0.0236 (6)
C110	0.4880 (3)	0.16019 (19)	0.52310 (13)	0.0233 (6)
C111	0.4389 (3)	0.08514 (19)	0.61330 (14)	0.0250 (6)
C112	0.2597 (3)	0.10638 (19)	0.64576 (14)	0.0255 (6)
C113	0.1267 (3)	0.20312 (19)	0.58927 (13)	0.0244 (6)
C114	0.6833 (3)	0.1366 (2)	0.48869 (14)	0.0276 (6)
H11	−0.100 (3)	0.388 (2)	0.4670 (14)	0.0331*
H12	−0.605 (3)	0.573 (2)	0.4203 (16)	0.0414*
H13	−0.53950	0.77225	0.19351	0.0315*
H14	−0.25413	0.78699	0.12011	0.0343*
H15	0.00682	0.65269	0.19740	0.0323*
H17	0.15512	0.47332	0.33554	0.0279*
H19	0.38328	0.30804	0.40501	0.0283*
H111	0.52913	0.01890	0.65276	0.0301*
H112	0.22822	0.05432	0.70700	0.0305*
H113	0.00417	0.21789	0.61164	0.0292*
H114	0.69231	0.19175	0.42273	0.0414*
H114'	0.73242	0.03956	0.49277	0.0414*
H114''	0.75207	0.16320	0.52821	0.0414*
O21	0.96821 (18)	0.15125 (13)	0.01479 (9)	0.0283 (4)
O22	1.14752 (19)	−0.09574 (13)	0.13003 (9)	0.0307 (4)
N2	0.8077 (2)	0.40206 (15)	−0.00512 (11)	0.0233 (5)
C21	1.0044 (2)	0.14475 (19)	0.10049 (13)	0.0223 (6)
C22	1.0979 (3)	0.01771 (19)	0.16170 (13)	0.0239 (6)
C23	1.1390 (3)	0.0095 (2)	0.25099 (13)	0.0264 (6)
C24	1.0891 (3)	0.1252 (2)	0.28508 (14)	0.0299 (7)
C25	0.9982 (3)	0.2484 (2)	0.22875 (14)	0.0300 (7)
C26	0.9559 (3)	0.26065 (19)	0.13608 (13)	0.0241 (6)
C27	0.8554 (2)	0.38820 (19)	0.07914 (13)	0.0237 (6)
C28	0.6973 (3)	0.51979 (18)	−0.06579 (13)	0.0228 (6)
C29	0.6510 (3)	0.64800 (19)	−0.04945 (13)	0.0242 (6)
C210	0.5397 (3)	0.75956 (19)	−0.11050 (14)	0.0266 (6)
C211	0.4770 (3)	0.7407 (2)	−0.18876 (14)	0.0279 (6)
C212	0.5210 (3)	0.6128 (2)	−0.20462 (14)	0.0277 (6)
C213	0.6311 (3)	0.5021 (2)	−0.14345 (13)	0.0253 (6)
C214	0.4838 (3)	0.89667 (19)	−0.09069 (15)	0.0339 (7)
H21	0.84194	0.32882	−0.02454	0.0406*
H22	1.10678	−0.07693	0.07670	0.0507*
H23	1.20220	−0.07562	0.29049	0.0317*
H24	1.11841	0.11778	0.34719	0.0359*
H25	0.96347	0.32610	0.25221	0.0360*
H27	0.82237	0.46507	0.10348	0.0284*
H29	0.69588	0.65928	0.00377	0.0291*
H211	0.40315	0.81636	−0.23179	0.0335*
H212	0.47534	0.60130	−0.25754	0.0332*
H213	0.66145	0.41471	−0.15429	0.0303*
H214	0.36087	0.91025	−0.06248	0.0507*
H214'	0.48750	0.96918	−0.15007	0.0507*
H214''	0.56659	0.89974	−0.04665	0.0507*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0243 (7)	0.0238 (7)	0.0328 (8)	−0.0047 (6)	−0.0006 (6)	0.0013 (6)
O12	0.0235 (8)	0.0288 (8)	0.0377 (9)	−0.0037 (6)	−0.0048 (6)	−0.0024 (7)
N1	0.0209 (9)	0.0205 (9)	0.0246 (9)	−0.0020 (7)	−0.0017 (7)	−0.0050 (7)
C11	0.0259 (11)	0.0175 (10)	0.0269 (11)	−0.0037 (8)	−0.0030 (8)	−0.0077 (8)
C12	0.0228 (10)	0.0201 (10)	0.0335 (12)	−0.0048 (8)	−0.0040 (8)	−0.0094 (9)
C13	0.0282 (11)	0.0197 (10)	0.0308 (12)	0.0002 (8)	−0.0100 (9)	−0.0094 (9)
C14	0.0358 (12)	0.0230 (10)	0.0243 (11)	−0.0020 (9)	−0.0022 (9)	−0.0071 (9)
C15	0.0277 (11)	0.0255 (11)	0.0246 (11)	−0.0026 (9)	0.0016 (8)	−0.0074 (9)
C16	0.0253 (10)	0.0194 (10)	0.0258 (11)	−0.0029 (8)	−0.0030 (8)	−0.0086 (8)
C17	0.0217 (10)	0.0233 (10)	0.0256 (11)	−0.0037 (8)	0.0002 (8)	−0.0103 (9)
C18	0.0242 (10)	0.0180 (10)	0.0231 (10)	−0.0007 (8)	−0.0056 (8)	−0.0072 (8)
C19	0.0282 (11)	0.0211 (10)	0.0213 (10)	−0.0067 (8)	0.0003 (8)	−0.0058 (8)
C110	0.0228 (10)	0.0213 (10)	0.0287 (11)	−0.0058 (8)	−0.0031 (8)	−0.0102 (8)
C111	0.0262 (11)	0.0211 (10)	0.0277 (11)	−0.0039 (8)	−0.0093 (8)	−0.0054 (8)
C112	0.0298 (11)	0.0239 (10)	0.0229 (10)	−0.0093 (9)	−0.0029 (8)	−0.0040 (8)
C113	0.0236 (10)	0.0246 (10)	0.0267 (11)	−0.0064 (8)	−0.0009 (8)	−0.0095 (9)
C114	0.0245 (11)	0.0263 (11)	0.0304 (11)	−0.0042 (9)	−0.0033 (8)	−0.0069 (9)
O21	0.0370 (8)	0.0228 (7)	0.0231 (8)	−0.0030 (6)	−0.0063 (6)	−0.0057 (6)
O22	0.0381 (8)	0.0217 (7)	0.0294 (8)	−0.0007 (6)	−0.0118 (6)	−0.0052 (6)
N2	0.0252 (9)	0.0181 (8)	0.0254 (9)	−0.0032 (7)	−0.0015 (7)	−0.0063 (7)
C21	0.0197 (10)	0.0252 (10)	0.0211 (10)	−0.0067 (8)	0.0012 (8)	−0.0050 (8)
C22	0.0211 (10)	0.0241 (10)	0.0254 (11)	−0.0061 (8)	−0.0025 (8)	−0.0046 (8)
C23	0.0222 (10)	0.0267 (11)	0.0260 (11)	−0.0062 (9)	−0.0046 (8)	0.0000 (9)
C24	0.0293 (11)	0.0378 (12)	0.0223 (11)	−0.0051 (10)	−0.0042 (9)	−0.0096 (9)
C25	0.0297 (11)	0.0310 (11)	0.0302 (12)	−0.0034 (9)	−0.0036 (9)	−0.0128 (9)
C26	0.0204 (10)	0.0245 (10)	0.0271 (11)	−0.0054 (8)	−0.0014 (8)	−0.0070 (9)
C27	0.0211 (10)	0.0228 (10)	0.0276 (11)	−0.0055 (8)	0.0008 (8)	−0.0085 (8)
C28	0.0218 (10)	0.0210 (10)	0.0218 (10)	−0.0060 (8)	0.0040 (8)	−0.0018 (8)
C29	0.0250 (10)	0.0240 (10)	0.0230 (10)	−0.0087 (8)	0.0035 (8)	−0.0051 (8)
C210	0.0226 (10)	0.0220 (10)	0.0304 (12)	−0.0061 (8)	0.0054 (8)	−0.0026 (9)
C211	0.0241 (10)	0.0236 (11)	0.0273 (11)	−0.0043 (8)	0.0012 (8)	0.0030 (9)
C212	0.0278 (11)	0.0301 (11)	0.0238 (11)	−0.0086 (9)	0.0007 (8)	−0.0049 (9)
C213	0.0249 (10)	0.0240 (10)	0.0259 (11)	−0.0065 (8)	0.0036 (8)	−0.0069 (9)
C214	0.0329 (12)	0.0218 (11)	0.0421 (13)	−0.0032 (9)	0.0011 (10)	−0.0063 (9)

Geometric parameters (Å, º)

O11—C11	1.306 (2)	C111—H111	0.9500
O12—C12	1.374 (3)	C112—H112	0.9500
O12—H12	0.91 (2)	C113—H113	0.9500
O21—C21	1.311 (2)	C114—H114	0.9800
O22—C22	1.365 (2)	C114—H114''	0.9800
O22—H22	0.8300	C114—H114'	0.9800
N1—C18	1.421 (3)	C21—C22	1.429 (3)
N1—C17	1.301 (2)	C21—C26	1.423 (3)
N1—H11	1.00 (2)	C22—C23	1.370 (3)
N2—C28	1.420 (3)	C23—C24	1.407 (3)
N2—C27	1.299 (2)	C24—C25	1.369 (3)
N2—H21	0.8700	C25—C26	1.410 (3)
C11—C12	1.428 (3)	C26—C27	1.426 (3)
C11—C16	1.430 (3)	C28—C213	1.396 (3)
C12—C13	1.369 (3)	C28—C29	1.396 (3)
C13—C14	1.413 (3)	C29—C210	1.392 (3)
C14—C15	1.375 (3)	C23—H23	0.9500
C15—C16	1.415 (3)	C24—H24	0.9500
C16—C17	1.430 (3)	C25—H25	0.9500
C18—C19	1.393 (3)	C27—H27	0.9500
C18—C113	1.384 (3)	C29—H29	0.9500
C19—C110	1.393 (3)	C210—C211	1.396 (3)
C110—C114	1.509 (3)	C210—C214	1.507 (3)
C110—C111	1.399 (3)	C211—C212	1.390 (3)
C111—C112	1.388 (3)	C212—C213	1.385 (3)
C112—C113	1.385 (3)	C211—H211	0.9500
C13—H13	0.9500	C212—H212	0.9500
C14—H14	0.9500	C213—H213	0.9500
C15—H15	0.9500	C214—H214'	0.9800
C17—H17	0.9500	C214—H214''	0.9800
C19—H19	0.9500	C214—H214	0.9800
O11···O12	2.719 (2)	C112···H114'^ix	2.9100
O11···N1	2.528 (2)	C212···C27^iv	3.253 (3)
O11···C114^i	3.321 (3)	C113···H114'^ix	3.0600
O11···O12^ii	2.774 (2)	C214···C22^vii	3.538 (3)
O11···O11^ii	3.166 (2)	C212···H17^iv	3.0800
O12···O11^ii	2.774 (2)	C212···H19^iv	2.8900
O12···O11	2.719 (2)	C212···H27^iv	3.0700
O21···N2	2.550 (2)	C213···H15^iv	2.9800
O21···O22^iii	2.6965 (19)	C213···H17^iv	3.0900
O21···O22	2.7501 (19)	H114'···C111^ix	2.9500
O22···O21^iii	2.6965 (19)	H114'···C112^ix	2.9100
O22···O21	2.7501 (19)	H114'···C113^ix	3.0600
O11···H12^ii	1.94 (2)	H114''···H23^xii	2.6000
O11···H12	2.29 (2)	H214'···H211	2.5400
O11···H11	1.61 (2)	H214'···C13^xi	3.0900
O12···H17^i	2.8000	H214''···H29	2.3800
O21···H22^iii	1.9700	H11···O11	1.61 (2)
O21···H14^iv	2.8700	H11···C11	2.22 (2)
O21···H21	1.8200	H11···H113	2.4000
O21···H214^iv	2.7500	H12···O11	2.29 (2)
O21···H22	2.3000	H12···O11^ii	1.94 (2)
O22···H13^v	2.5700	H13···O22^xiv	2.5700
N1···O11	2.528 (2)	H14···O21^iv	2.8700
N2···O21	2.550 (2)	H15···H213^iv	2.5200
C11···C113^vi	3.525 (3)	H15···H17	2.4800
C11···C18^vi	3.479 (3)	H15···C213^iv	2.9800
C12···C111^vi	3.500 (3)	H17···O12^viii	2.8000
C14···C112^vi	3.540 (3)	H17···C19	2.7300
C15···C113^vi	3.528 (3)	H17···H15	2.4800
C15···C112^vi	3.557 (3)	H17···H19	2.2100
C16···C113^vi	3.266 (3)	H17···C213^iv	3.0900
C17···C25^i	3.581 (3)	H17···C212^iv	3.0800
C18···C11^vi	3.479 (3)	H19···H17	2.2100
C22···C214^vii	3.538 (3)	H19···C17	2.7400
C25···C17^viii	3.581 (3)	H19···H212^iv	2.3700
C26···C211^iv	3.337 (3)	H19···H114	2.3700
C26···C29^vii	3.416 (3)	H19···C212^iv	2.8900
C27···C212^iv	3.253 (3)	H21···O21	1.8200
C27···C211^iv	3.258 (3)	H21···C21	2.4200
C28···C28^iv	3.464 (3)	H21···H213	2.3200
C28···C29^iv	3.595 (3)	H22···O21	2.3000
C29···C26^vii	3.416 (3)	H22···O21^iii	1.9700
C29···C28^iv	3.595 (3)	H23···H114''^xii	2.6000
C111···C114^ix	3.522 (3)	H23···H113^ix	2.5100
C11···H11	2.22 (2)	H25···C16^viii	2.7500
C111···C12^vi	3.500 (3)	H25···C17^viii	2.7400
C112···C15^vi	3.557 (3)	H25···H27	2.4400
C112···C14^vi	3.540 (3)	H27···C212^iv	3.0700
C12···H212^x	2.9000	H27···C29	2.7000
C13···H213^x	2.9800	H27···H25	2.4400
C13···H214'^xi	3.0900	H27···H29	2.1900
C113···C15^vi	3.528 (3)	H29···H214''	2.3800
C113···C11^vi	3.525 (3)	H29···H27	2.1900
C113···C16^vi	3.266 (3)	H29···C27	2.7300
C14···H29^i	3.0000	H29···C14^viii	3.0000
C114···O11^viii	3.321 (3)	H111···C24^xii	3.0300
C114···C111^ix	3.522 (3)	H111···C23^xii	2.9800
C16···H25^i	2.7500	H112···H211^xiii	2.4600
C17···H25^i	2.7400	H112···C23^ix	3.0400
C17···H19	2.7400	H113···H23^ix	2.5100
C19···H17	2.7300	H113···H11	2.4000
C21···H21	2.4200	H113···C23^ix	3.0100
C23···H111^xii	2.9800	H114···H19	2.3700
C23···H113^ix	3.0100	H211···C112^xv	3.0300
C23···H112^ix	3.0400	H211···H214'	2.5400
C24···H111^xii	3.0300	H211···H112^xv	2.4600
C27···H29	2.7300	H212···C12^x	2.9000
C29···H27	2.7000	H212···H19^iv	2.3700
C111···H114'^ix	2.9500	H213···H21	2.3200
C211···C26^iv	3.337 (3)	H213···C13^x	2.9800
C211···C27^iv	3.258 (3)	H213···H15^iv	2.5200
C112···H211^xiii	3.0300	H214···O21^iv	2.7500
C12—O12—H12	112.3 (15)	H114'—C114—H114''	109.00
C22—O22—H22	109.00	C110—C114—H114''	109.00
C17—N1—C18	128.16 (18)	H114''—C114—H114	109.00
C18—N1—H11	124.2 (12)	C110—C114—H114'	109.00
C17—N1—H11	107.7 (12)	O21—C21—C22	119.87 (18)
C27—N2—C28	127.22 (17)	O21—C21—C26	122.64 (17)
C27—N2—H21	116.00	C22—C21—C26	117.48 (17)
C28—N2—H21	117.00	O22—C22—C23	120.09 (18)
O11—C11—C12	119.7 (2)	O22—C22—C21	119.27 (16)
O11—C11—C16	122.90 (19)	C21—C22—C23	120.64 (18)
C12—C11—C16	117.37 (17)	C22—C23—C24	121.03 (19)
O12—C12—C13	120.8 (2)	C23—C24—C25	119.99 (19)
O12—C12—C11	117.88 (17)	C24—C25—C26	120.37 (19)
C11—C12—C13	121.3 (2)	C25—C26—C27	119.97 (18)
C12—C13—C14	120.6 (2)	C21—C26—C27	119.47 (17)
C13—C14—C15	120.22 (19)	C21—C26—C25	120.48 (18)
C14—C15—C16	120.2 (2)	N2—C27—C26	121.76 (18)
C11—C16—C17	118.95 (17)	N2—C28—C29	123.01 (18)
C15—C16—C17	120.7 (2)	N2—C28—C213	116.87 (17)
C11—C16—C15	120.3 (2)	C29—C28—C213	120.11 (19)
N1—C17—C16	120.9 (2)	C28—C29—C210	120.57 (19)
N1—C18—C113	116.4 (2)	C22—C23—H23	119.00
C19—C18—C113	120.49 (19)	C24—C23—H23	119.00
N1—C18—C19	123.11 (17)	C23—C24—H24	120.00
C18—C19—C110	120.52 (18)	C25—C24—H24	120.00
C19—C110—C114	121.28 (18)	C26—C25—H25	120.00
C111—C110—C114	120.28 (19)	C24—C25—H25	120.00
C19—C110—C111	118.5 (2)	C26—C27—H27	119.00
C110—C111—C112	120.7 (2)	N2—C27—H27	119.00
C111—C112—C113	120.30 (19)	C28—C29—H29	120.00
C18—C113—C112	119.5 (2)	C210—C29—H29	120.00
C14—C13—H13	120.00	C29—C210—C211	118.63 (19)
C12—C13—H13	120.00	C211—C210—C214	120.81 (19)
C15—C14—H14	120.00	C29—C210—C214	120.53 (18)
C13—C14—H14	120.00	C210—C211—C212	120.96 (19)
C16—C15—H15	120.00	C211—C212—C213	120.15 (19)
C14—C15—H15	120.00	C28—C213—C212	119.57 (19)
N1—C17—H17	120.00	C210—C211—H211	120.00
C16—C17—H17	120.00	C212—C211—H211	119.00
C110—C19—H19	120.00	C211—C212—H212	120.00
C18—C19—H19	120.00	C213—C212—H212	120.00
C112—C111—H111	120.00	C28—C213—H213	120.00
C110—C111—H111	120.00	C212—C213—H213	120.00
C111—C112—H112	120.00	C210—C214—H214'	109.00
C113—C112—H112	120.00	C210—C214—H214''	109.00
C18—C113—H113	120.00	C210—C214—H214	109.00
C112—C113—H113	120.00	H214'—C214—H214''	109.00
H114'—C114—H114	109.00	H214'—C214—H214	109.00
C110—C114—H114	109.00	H214''—C214—H214	109.00
C18—N1—C17—C16	177.46 (18)	C18—C19—C110—C114	−179.28 (19)
C17—N1—C18—C19	−6.6 (3)	O21—C21—C22—O22	−0.4 (3)
C17—N1—C18—C113	173.7 (2)	O21—C21—C22—C23	179.10 (19)
C27—N2—C28—C213	−166.06 (19)	C26—C21—C22—O22	−179.70 (19)
C28—N2—C27—C26	175.1 (2)	C26—C21—C22—C23	−0.3 (3)
C27—N2—C28—C29	12.5 (3)	O21—C21—C26—C25	−179.88 (19)
O11—C11—C12—O12	−0.2 (3)	O21—C21—C26—C27	3.5 (3)
O11—C11—C12—C13	−178.69 (19)	C22—C21—C26—C25	−0.6 (3)
C16—C11—C12—O12	179.65 (17)	C22—C21—C26—C27	−177.22 (19)
C16—C11—C12—C13	1.1 (3)	O22—C22—C23—C24	−180.0 (2)
C12—C11—C16—C17	−178.94 (18)	C21—C22—C23—C24	0.6 (3)
O11—C11—C16—C15	−179.40 (18)	C22—C23—C24—C25	−0.1 (4)
O11—C11—C16—C17	0.9 (3)	C23—C24—C25—C26	−0.8 (4)
C12—C11—C16—C15	0.8 (3)	C24—C25—C26—C21	1.1 (3)
O12—C12—C13—C14	179.53 (18)	C24—C25—C26—C27	177.7 (2)
C11—C12—C13—C14	−2.0 (3)	C21—C26—C27—N2	−0.6 (3)
C12—C13—C14—C15	0.9 (3)	C25—C26—C27—N2	−177.2 (2)
C13—C14—C15—C16	1.1 (3)	N2—C28—C29—C210	−178.9 (2)
C14—C15—C16—C17	177.86 (19)	C213—C28—C29—C210	−0.4 (3)
C14—C15—C16—C11	−1.9 (3)	C29—C28—C213—C212	0.7 (3)
C15—C16—C17—N1	−176.80 (19)	N2—C28—C213—C212	179.3 (2)
C11—C16—C17—N1	2.9 (3)	C28—C29—C210—C214	177.6 (2)
N1—C18—C19—C110	179.63 (18)	C28—C29—C210—C211	−0.6 (3)
C113—C18—C19—C110	−0.6 (3)	C29—C210—C211—C212	1.4 (3)
C19—C18—C113—C112	0.2 (3)	C214—C210—C211—C212	−176.8 (2)
N1—C18—C113—C112	179.97 (18)	C210—C211—C212—C213	−1.2 (3)
C18—C19—C110—C111	0.5 (3)	C211—C212—C213—C28	0.1 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O11	1.00 (2)	1.61 (2)	2.528 (2)	150.8 (18)
O12—H12···O11	0.91 (2)	2.29 (2)	2.719 (2)	108.7 (18)
O12—H12···O11^ii	0.91 (2)	1.94 (2)	2.774 (2)	152 (2)
N2—H21···O21	0.8700	1.8200	2.550 (2)	140.00
O22—H22···O21	0.8300	2.3000	2.7501 (19)	114.00
O22—H22···O21^iii	0.8300	1.9700	2.6965 (19)	145.00
C13—H13···O22^xiv	0.9500	2.5700	3.507 (3)	171.00

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