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The title compound, C28H40N2O2·0.5CH3OH, crystallizes with two mol­ecules of 1-{2-[(2-hydr­oxy-1-naphth­yl)methyl­eneamino]phenyl­iminiometh­yl}-2-naphtholate and one methanol solvent mol­ecule in the asymmetric unit. All bond lengths and angles are normal. The crystal structure is stabilized by π–π, O—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050707/cv2159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050707/cv2159Isup2.hkl
Contains datablock I

CCDC reference: 633669

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.108
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.65 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 17
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 30.27 From the CIF: _reflns_number_total 6547 Count of symmetry unique reflns 6599 Completeness (_total/calc) 99.21% 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 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

N,N'-Bis(2-hydroxy-1-naphthaldimine)-o-phenylenediamine methanol hemisolvate top
Crystal data top
C28H20N2O2·0.5CH4ODx = 1.339 Mg m3
Mr = 432.48Melting point = 495–496 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 6999 reflections
a = 19.3610 (3) Åθ = 1.9–30.3°
b = 12.5103 (2) ŵ = 0.09 mm1
c = 17.7128 (2) ÅT = 100 K
V = 4290.25 (11) Å3Plate, red
Z = 80.31 × 0.30 × 0.18 mm
F(000) = 1816
Data collection top
Bruker SMART APEX2 CCD
diffractometer
6547 independent reflections
Radiation source: fine-focus sealed tube5671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 8.33 pixels mm-1θmax = 30.3°, θmin = 1.9°
ω scansh = 2721
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1317
Tmin = 0.962, Tmax = 0.985l = 2525
52989 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.8098P]
where P = (Fo2 + 2Fc2)/3
6547 reflections(Δ/σ)max < 0.001
616 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.22 e Å3
Special details top

Experimental. IR spectroscopy (KBr, cm-1): v(O—H) 3362, v(C—H) 3026, 2927, v(CN) 1621, v(CC) 1569, 1542, 1484, v(C—O) 1323, v(C—N) 1288.

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 (Å2) top
xyzUiso*/Ueq
O1A0.30965 (9)0.52962 (13)0.33505 (9)0.0295 (4)
O2A0.45989 (9)0.42788 (13)0.30325 (10)0.0277 (3)
N1A0.25929 (9)0.43169 (14)0.22197 (10)0.0211 (4)
N2A0.36524 (9)0.30052 (14)0.25278 (10)0.0216 (4)
C1A0.47215 (11)0.35347 (18)0.35645 (12)0.0232 (4)
C2A0.52540 (11)0.3770 (2)0.40849 (14)0.0283 (5)
H2AA0.54990.44070.40470.034*
C3A0.54074 (13)0.3060 (2)0.46418 (13)0.0305 (5)
H3AA0.57640.32160.49760.037*
C4A0.50380 (13)0.20875 (19)0.47273 (13)0.0293 (5)
C5A0.51925 (15)0.1369 (2)0.53206 (14)0.0366 (6)
H5AA0.55510.15270.56520.044*
C6A0.48242 (15)0.0447 (2)0.54150 (14)0.0396 (7)
H6AA0.49310.00190.58070.048*
C7A0.42844 (15)0.0209 (2)0.49165 (14)0.0361 (6)
H7AA0.40300.04140.49850.043*
C8A0.41244 (13)0.08812 (19)0.43276 (13)0.0288 (5)
H8AA0.37660.07040.40020.035*
C9A0.44989 (12)0.18415 (18)0.42104 (12)0.0241 (4)
C10A0.43542 (11)0.25761 (17)0.36013 (12)0.0217 (4)
C11A0.38555 (11)0.23131 (17)0.30204 (12)0.0214 (4)
H11A0.36760.16240.30020.026*
C12A0.31889 (11)0.26843 (17)0.19529 (12)0.0216 (4)
C13A0.32625 (12)0.17329 (18)0.15480 (13)0.0262 (5)
H13A0.36230.12670.16590.031*
C14A0.27966 (13)0.14852 (19)0.09790 (13)0.0290 (5)
H14A0.28460.08530.07080.035*
C15A0.22571 (14)0.2177 (2)0.08130 (12)0.0306 (5)
H15A0.19450.20030.04340.037*
C16A0.21802 (12)0.31259 (19)0.12084 (12)0.0252 (5)
H16A0.18180.35860.10940.030*
C17A0.26470 (12)0.33887 (17)0.17784 (12)0.0224 (4)
C18A0.21546 (11)0.51138 (17)0.21504 (12)0.0213 (4)
H18A0.18320.50900.17620.026*
C19A0.21530 (11)0.59964 (17)0.26364 (12)0.0208 (4)
C20A0.16713 (11)0.68771 (17)0.25304 (12)0.0222 (4)
C21A0.11676 (11)0.69027 (18)0.19520 (14)0.0261 (5)
H21A0.11270.63240.16260.031*
C22A0.07359 (12)0.77724 (19)0.18638 (16)0.0313 (5)
H22A0.04140.77750.14740.038*
C23A0.07760 (12)0.86447 (19)0.23494 (16)0.0314 (5)
H23A0.04870.92310.22820.038*
C24A0.12459 (12)0.8632 (2)0.29289 (15)0.0296 (5)
H24A0.12650.92050.32630.036*
C25A0.17005 (12)0.77591 (18)0.30233 (13)0.0252 (4)
C26A0.22009 (12)0.7772 (2)0.36211 (13)0.0285 (5)
H26A0.22150.83550.39470.034*
C27A0.26511 (12)0.6961 (2)0.37240 (13)0.0296 (5)
H27A0.29680.70000.41180.036*
C28A0.26528 (11)0.60390 (19)0.32405 (12)0.0245 (4)
O1B0.01744 (8)0.45705 (13)0.22582 (9)0.0269 (3)
O2B0.16613 (9)0.57643 (12)0.24949 (10)0.0278 (4)
N1B0.03332 (9)0.55339 (14)0.34063 (10)0.0199 (3)
N2B0.07045 (9)0.69059 (14)0.31357 (10)0.0210 (3)
C1B0.17404 (11)0.65861 (16)0.20135 (13)0.0225 (4)
C2B0.22445 (12)0.64717 (19)0.14421 (14)0.0268 (5)
H2BA0.24980.58420.14090.032*
C3B0.23620 (12)0.72732 (19)0.09412 (13)0.0279 (5)
H3BA0.27010.71870.05740.033*
C4B0.19765 (11)0.82437 (18)0.09657 (12)0.0231 (4)
C5B0.20958 (13)0.9084 (2)0.04424 (13)0.0306 (5)
H5BA0.24470.90150.00870.037*
C6B0.17021 (13)0.9994 (2)0.04526 (12)0.0300 (5)
H6BA0.17801.05330.01020.036*
C7B0.11797 (12)1.01043 (18)0.09976 (12)0.0261 (5)
H7BA0.09101.07190.10030.031*
C8B0.10625 (11)0.93202 (16)0.15212 (12)0.0213 (4)
H8BA0.07170.94150.18800.026*
C9B0.14577 (11)0.83669 (16)0.15257 (11)0.0196 (4)
C10B0.13516 (10)0.75239 (16)0.20707 (11)0.0182 (4)
C11B0.08716 (11)0.76706 (16)0.26833 (12)0.0201 (4)
H11B0.06750.83410.27550.024*
C12B0.02510 (11)0.71500 (16)0.37378 (12)0.0204 (4)
C13B0.03167 (12)0.80674 (17)0.41767 (13)0.0253 (5)
H13B0.06670.85540.40740.030*
C14B0.01382 (13)0.82580 (18)0.47657 (14)0.0280 (5)
H14B0.00890.88660.50630.034*
C15B0.06704 (12)0.75349 (18)0.49120 (13)0.0254 (4)
H15B0.09780.76660.53040.030*
C16B0.07427 (11)0.66253 (17)0.44777 (12)0.0220 (4)
H16B0.10980.61470.45790.026*
C17B0.02850 (10)0.64220 (16)0.38881 (12)0.0193 (4)
C18B0.07771 (10)0.47291 (16)0.34571 (12)0.0192 (4)
H18B0.11000.47360.38460.023*
C19B0.07815 (11)0.38751 (16)0.29545 (12)0.0197 (4)
C20B0.12756 (11)0.30017 (16)0.30475 (12)0.0205 (4)
C21B0.18003 (11)0.30054 (17)0.35967 (13)0.0230 (4)
H21B0.18440.35890.39180.028*
C22B0.22517 (12)0.21559 (18)0.36667 (13)0.0261 (5)
H22B0.25970.21770.40310.031*
C23B0.21940 (12)0.12636 (18)0.31931 (14)0.0297 (5)
H23B0.24920.06860.32490.036*
C24B0.16931 (12)0.12501 (18)0.26459 (14)0.0285 (5)
H24B0.16580.06630.23260.034*
C25B0.12313 (11)0.21098 (17)0.25598 (13)0.0236 (4)
C26B0.07234 (12)0.21018 (18)0.19700 (13)0.0272 (5)
H26B0.07010.15130.16500.033*
C27B0.02767 (12)0.29161 (19)0.18617 (13)0.0261 (5)
H27B0.00340.28830.14620.031*
C28B0.02712 (11)0.38385 (17)0.23526 (12)0.0222 (4)
O30.30354 (11)0.4610 (2)0.48317 (12)0.0498 (5)
C290.36808 (14)0.4531 (2)0.51869 (16)0.0414 (6)
H29A0.36170.44860.57230.062*
H29B0.39530.51510.50690.062*
H29C0.39150.39010.50120.062*
H1NA0.2889 (19)0.442 (3)0.259 (2)0.066 (11)*
H1NB0.0043 (15)0.545 (2)0.3010 (18)0.031 (7)*
H2OA0.4243 (18)0.410 (3)0.277 (2)0.055 (10)*
H2OB0.129 (2)0.598 (3)0.281 (2)0.084 (14)*
HO30.312 (2)0.481 (3)0.433 (3)0.079 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0288 (8)0.0376 (9)0.0220 (7)0.0050 (7)0.0057 (7)0.0006 (7)
O2A0.0264 (8)0.0241 (8)0.0325 (9)0.0028 (6)0.0043 (7)0.0022 (7)
N1A0.0218 (9)0.0239 (9)0.0175 (8)0.0037 (7)0.0031 (7)0.0016 (7)
N2A0.0215 (9)0.0217 (8)0.0215 (8)0.0019 (7)0.0009 (7)0.0002 (7)
C1A0.0223 (10)0.0240 (10)0.0234 (10)0.0040 (8)0.0015 (8)0.0027 (8)
C2A0.0228 (11)0.0324 (12)0.0296 (11)0.0009 (8)0.0003 (9)0.0085 (10)
C3A0.0280 (12)0.0401 (13)0.0234 (11)0.0097 (9)0.0036 (9)0.0109 (10)
C4A0.0328 (13)0.0355 (13)0.0196 (10)0.0147 (9)0.0014 (9)0.0060 (9)
C5A0.0472 (16)0.0422 (15)0.0204 (10)0.0213 (12)0.0034 (10)0.0019 (10)
C6A0.0566 (17)0.0416 (15)0.0208 (11)0.0251 (13)0.0024 (11)0.0046 (11)
C7A0.0507 (16)0.0306 (13)0.0269 (11)0.0137 (11)0.0117 (11)0.0050 (10)
C8A0.0339 (12)0.0285 (12)0.0239 (10)0.0091 (9)0.0053 (10)0.0020 (9)
C9A0.0265 (11)0.0261 (11)0.0198 (10)0.0086 (8)0.0039 (8)0.0016 (9)
C10A0.0225 (10)0.0214 (10)0.0210 (9)0.0055 (7)0.0025 (8)0.0003 (8)
C11A0.0214 (10)0.0195 (9)0.0233 (9)0.0014 (7)0.0051 (8)0.0003 (8)
C12A0.0237 (11)0.0223 (10)0.0188 (9)0.0055 (8)0.0019 (8)0.0035 (8)
C13A0.0308 (12)0.0245 (11)0.0233 (10)0.0040 (8)0.0054 (9)0.0004 (9)
C14A0.0388 (13)0.0275 (12)0.0207 (10)0.0117 (9)0.0046 (9)0.0032 (9)
C15A0.0395 (14)0.0358 (13)0.0166 (10)0.0146 (10)0.0028 (9)0.0004 (9)
C16A0.0275 (11)0.0283 (11)0.0197 (10)0.0069 (9)0.0021 (9)0.0041 (9)
C17A0.0260 (11)0.0232 (10)0.0181 (9)0.0056 (8)0.0014 (8)0.0032 (8)
C18A0.0195 (10)0.0269 (10)0.0174 (9)0.0035 (7)0.0004 (8)0.0048 (8)
C19A0.0180 (10)0.0261 (10)0.0182 (9)0.0017 (7)0.0005 (8)0.0034 (8)
C20A0.0193 (10)0.0248 (10)0.0224 (10)0.0045 (7)0.0028 (8)0.0038 (8)
C21A0.0228 (11)0.0256 (11)0.0299 (11)0.0033 (8)0.0016 (9)0.0009 (9)
C22A0.0225 (12)0.0333 (12)0.0381 (13)0.0029 (9)0.0038 (10)0.0064 (11)
C23A0.0246 (11)0.0232 (11)0.0465 (15)0.0003 (8)0.0021 (10)0.0036 (10)
C24A0.0268 (12)0.0275 (11)0.0346 (12)0.0031 (9)0.0075 (10)0.0020 (10)
C25A0.0228 (11)0.0286 (11)0.0243 (10)0.0033 (8)0.0049 (9)0.0027 (9)
C26A0.0287 (12)0.0350 (13)0.0219 (10)0.0008 (9)0.0032 (9)0.0072 (9)
C27A0.0266 (12)0.0447 (14)0.0175 (10)0.0014 (10)0.0007 (9)0.0023 (10)
C28A0.0221 (11)0.0329 (12)0.0183 (10)0.0008 (8)0.0013 (8)0.0008 (9)
O1B0.0258 (8)0.0288 (8)0.0262 (8)0.0019 (6)0.0045 (7)0.0001 (7)
O2B0.0274 (8)0.0200 (8)0.0358 (9)0.0040 (6)0.0042 (7)0.0020 (7)
N1B0.0204 (9)0.0188 (8)0.0205 (8)0.0009 (6)0.0014 (7)0.0007 (7)
N2B0.0205 (8)0.0198 (8)0.0227 (8)0.0005 (6)0.0012 (7)0.0006 (7)
C1B0.0218 (10)0.0193 (10)0.0263 (11)0.0009 (7)0.0003 (9)0.0034 (8)
C2B0.0238 (11)0.0267 (11)0.0298 (11)0.0020 (8)0.0014 (9)0.0087 (9)
C3B0.0259 (11)0.0331 (12)0.0246 (10)0.0028 (9)0.0077 (9)0.0095 (9)
C4B0.0248 (11)0.0272 (11)0.0172 (9)0.0050 (8)0.0009 (8)0.0050 (8)
C5B0.0375 (13)0.0363 (13)0.0182 (10)0.0099 (10)0.0058 (9)0.0041 (9)
C6B0.0434 (14)0.0291 (12)0.0175 (10)0.0114 (10)0.0015 (10)0.0023 (9)
C7B0.0345 (12)0.0215 (10)0.0223 (10)0.0032 (8)0.0063 (9)0.0005 (9)
C8B0.0235 (10)0.0213 (10)0.0192 (9)0.0030 (7)0.0020 (8)0.0007 (8)
C9B0.0210 (10)0.0206 (10)0.0173 (9)0.0035 (7)0.0021 (8)0.0034 (8)
C10B0.0176 (9)0.0186 (9)0.0185 (9)0.0016 (7)0.0011 (7)0.0005 (7)
C11B0.0202 (10)0.0181 (9)0.0220 (9)0.0003 (7)0.0008 (8)0.0022 (8)
C12B0.0217 (10)0.0177 (9)0.0218 (10)0.0017 (7)0.0010 (8)0.0020 (8)
C13B0.0276 (11)0.0210 (10)0.0272 (11)0.0049 (8)0.0041 (9)0.0004 (9)
C14B0.0352 (13)0.0222 (10)0.0267 (11)0.0038 (9)0.0042 (10)0.0043 (9)
C15B0.0298 (11)0.0254 (11)0.0210 (9)0.0010 (8)0.0050 (9)0.0003 (9)
C16B0.0235 (10)0.0209 (10)0.0217 (10)0.0010 (7)0.0030 (8)0.0037 (8)
C17B0.0195 (10)0.0188 (9)0.0196 (9)0.0013 (7)0.0005 (8)0.0023 (8)
C18B0.0179 (9)0.0204 (10)0.0193 (9)0.0016 (7)0.0004 (7)0.0026 (8)
C19B0.0193 (10)0.0201 (10)0.0198 (9)0.0007 (7)0.0031 (8)0.0025 (8)
C20B0.0217 (10)0.0195 (10)0.0204 (9)0.0000 (7)0.0068 (8)0.0018 (8)
C21B0.0232 (10)0.0237 (10)0.0221 (9)0.0009 (8)0.0056 (8)0.0038 (8)
C22B0.0239 (11)0.0284 (11)0.0262 (11)0.0028 (8)0.0037 (9)0.0081 (9)
C23B0.0287 (12)0.0231 (11)0.0374 (13)0.0060 (8)0.0081 (10)0.0053 (10)
C24B0.0327 (12)0.0208 (10)0.0319 (12)0.0011 (9)0.0122 (10)0.0002 (9)
C25B0.0243 (11)0.0206 (10)0.0258 (10)0.0016 (7)0.0077 (9)0.0000 (8)
C26B0.0310 (12)0.0249 (11)0.0256 (11)0.0045 (8)0.0062 (9)0.0044 (9)
C27B0.0255 (11)0.0297 (11)0.0230 (10)0.0057 (8)0.0007 (9)0.0037 (9)
C28B0.0224 (10)0.0237 (10)0.0206 (10)0.0025 (8)0.0005 (8)0.0016 (8)
O30.0384 (11)0.0768 (15)0.0342 (10)0.0022 (10)0.0018 (9)0.0200 (11)
C290.0376 (15)0.0487 (16)0.0380 (15)0.0013 (12)0.0063 (11)0.0098 (13)
Geometric parameters (Å, º) top
O1A—C28A1.280 (3)N1B—C17B1.404 (3)
O2A—C1A1.346 (3)N1B—H1NB0.91 (3)
O2A—H2OA0.86 (4)N2B—C11B1.289 (3)
N1A—C18A1.315 (3)N2B—C12B1.415 (3)
N1A—C17A1.404 (3)C1B—C10B1.398 (3)
N1A—H1NA0.89 (4)C1B—C2B1.413 (3)
N2A—C11A1.291 (3)C2B—C3B1.358 (3)
N2A—C12A1.415 (3)C2B—H2BA0.9300
C1A—C10A1.396 (3)C3B—C4B1.426 (3)
C1A—C2A1.414 (3)C3B—H3BA0.9300
C2A—C3A1.360 (3)C4B—C9B1.420 (3)
C2A—H2AA0.9300C4B—C5B1.420 (3)
C3A—C4A1.419 (4)C5B—C6B1.370 (4)
C3A—H3AA0.9300C5B—H5BA0.9300
C4A—C5A1.415 (3)C6B—C7B1.405 (3)
C4A—C9A1.422 (3)C6B—H6BA0.9300
C5A—C6A1.366 (4)C7B—C8B1.369 (3)
C5A—H5AA0.9300C7B—H7BA0.9300
C6A—C7A1.400 (4)C8B—C9B1.417 (3)
C6A—H6AA0.9300C8B—H8BA0.9300
C7A—C8A1.375 (3)C9B—C10B1.444 (3)
C7A—H7AA0.9300C10B—C11B1.440 (3)
C8A—C9A1.418 (3)C11B—H11B0.9300
C8A—H8AA0.9300C12B—C13B1.392 (3)
C9A—C10A1.445 (3)C12B—C17B1.406 (3)
C10A—C11A1.449 (3)C13B—C14B1.386 (3)
C11A—H11A0.9300C13B—H13B0.9300
C12A—C13A1.397 (3)C14B—C15B1.395 (3)
C12A—C17A1.405 (3)C14B—H14B0.9300
C13A—C14A1.388 (3)C15B—C16B1.381 (3)
C13A—H13A0.9300C15B—H15B0.9300
C14A—C15A1.388 (4)C16B—C17B1.393 (3)
C14A—H14A0.9300C16B—H16B0.9300
C15A—C16A1.386 (3)C18B—C19B1.391 (3)
C15A—H15A0.9300C18B—H18B0.9300
C16A—C17A1.394 (3)C19B—C28B1.454 (3)
C16A—H16A0.9300C19B—C20B1.461 (3)
C18A—C19A1.400 (3)C20B—C21B1.407 (3)
C18A—H18A0.9300C20B—C25B1.414 (3)
C19A—C28A1.444 (3)C21B—C22B1.382 (3)
C19A—C20A1.456 (3)C21B—H21B0.9300
C20A—C25A1.408 (3)C22B—C23B1.401 (3)
C20A—C21A1.415 (3)C22B—H22B0.9300
C21A—C22A1.381 (3)C23B—C24B1.371 (4)
C21A—H21A0.9300C23B—H23B0.9300
C22A—C23A1.392 (4)C24B—C25B1.407 (3)
C22A—H22A0.9300C24B—H24B0.9300
C23A—C24A1.372 (4)C25B—C26B1.435 (3)
C23A—H23A0.9300C26B—C27B1.350 (3)
C24A—C25A1.413 (3)C26B—H26B0.9300
C24A—H24A0.9300C27B—C28B1.445 (3)
C25A—C26A1.435 (3)C27B—H27B0.9300
C26A—C27A1.350 (3)O3—C291.403 (3)
C26A—H26A0.9300O3—HO30.94 (5)
C27A—C28A1.436 (3)C29—H29A0.9600
C27A—H27A0.9300C29—H29B0.9600
O1B—C28B1.269 (3)C29—H29C0.9600
O2B—C1B1.344 (3)Cg1—Cg2i3.569 (1)
O2B—H2OB0.94 (4)Cg3—Cg4ii3.562 (1)
N1B—C18B1.327 (3)Cg5—Cg63.637 (1)
C1A—O2A—H2OA110 (2)C11B—N2B—C12B117.65 (17)
C18A—N1A—C17A128.57 (19)O2B—C1B—C10B122.32 (19)
C18A—N1A—H1NA112 (2)O2B—C1B—C2B117.09 (19)
C17A—N1A—H1NA120 (2)C10B—C1B—C2B120.6 (2)
C11A—N2A—C12A119.29 (18)C3B—C2B—C1B120.6 (2)
O2A—C1A—C10A122.5 (2)C3B—C2B—H2BA119.7
O2A—C1A—C2A116.2 (2)C1B—C2B—H2BA119.7
C10A—C1A—C2A121.3 (2)C2B—C3B—C4B121.4 (2)
C3A—C2A—C1A119.8 (2)C2B—C3B—H3BA119.3
C3A—C2A—H2AA120.1C4B—C3B—H3BA119.3
C1A—C2A—H2AA120.1C9B—C4B—C5B119.4 (2)
C2A—C3A—C4A121.8 (2)C9B—C4B—C3B118.9 (2)
C2A—C3A—H3AA119.1C5B—C4B—C3B121.7 (2)
C4A—C3A—H3AA119.1C6B—C5B—C4B121.0 (2)
C5A—C4A—C3A121.1 (2)C6B—C5B—H5BA119.5
C5A—C4A—C9A119.7 (2)C4B—C5B—H5BA119.5
C3A—C4A—C9A119.1 (2)C5B—C6B—C7B119.4 (2)
C6A—C5A—C4A121.1 (3)C5B—C6B—H6BA120.3
C6A—C5A—H5AA119.4C7B—C6B—H6BA120.3
C4A—C5A—H5AA119.4C8B—C7B—C6B121.0 (2)
C5A—C6A—C7A119.5 (2)C8B—C7B—H7BA119.5
C5A—C6A—H6AA120.3C6B—C7B—H7BA119.5
C7A—C6A—H6AA120.3C7B—C8B—C9B121.2 (2)
C8A—C7A—C6A121.1 (3)C7B—C8B—H8BA119.4
C8A—C7A—H7AA119.5C9B—C8B—H8BA119.4
C6A—C7A—H7AA119.5C8B—C9B—C4B118.00 (19)
C7A—C8A—C9A120.9 (2)C8B—C9B—C10B122.77 (19)
C7A—C8A—H8AA119.5C4B—C9B—C10B119.23 (19)
C9A—C8A—H8AA119.5C1B—C10B—C11B120.61 (19)
C8A—C9A—C4A117.7 (2)C1B—C10B—C9B119.19 (18)
C8A—C9A—C10A123.3 (2)C11B—C10B—C9B120.15 (18)
C4A—C9A—C10A119.0 (2)N2B—C11B—C10B122.38 (19)
C1A—C10A—C9A118.9 (2)N2B—C11B—H11B118.8
C1A—C10A—C11A120.10 (19)C10B—C11B—H11B118.8
C9A—C10A—C11A121.0 (2)C13B—C12B—C17B119.72 (19)
N2A—C11A—C10A122.07 (19)C13B—C12B—N2B122.83 (19)
N2A—C11A—H11A119.0C17B—C12B—N2B117.45 (18)
C10A—C11A—H11A119.0C14B—C13B—C12B120.3 (2)
C13A—C12A—C17A119.9 (2)C14B—C13B—H13B119.9
C13A—C12A—N2A123.1 (2)C12B—C13B—H13B119.9
C17A—C12A—N2A117.00 (19)C13B—C14B—C15B119.8 (2)
C14A—C13A—C12A119.8 (2)C13B—C14B—H14B120.1
C14A—C13A—H13A120.1C15B—C14B—H14B120.1
C12A—C13A—H13A120.1C16B—C15B—C14B120.4 (2)
C13A—C14A—C15A120.3 (2)C16B—C15B—H15B119.8
C13A—C14A—H14A119.9C14B—C15B—H15B119.8
C15A—C14A—H14A119.9C15B—C16B—C17B120.24 (19)
C16A—C15A—C14A120.5 (2)C15B—C16B—H16B119.9
C16A—C15A—H15A119.7C17B—C16B—H16B119.9
C14A—C15A—H15A119.7C16B—C17B—N1B123.91 (19)
C15A—C16A—C17A119.9 (2)C16B—C17B—C12B119.55 (19)
C15A—C16A—H16A120.1N1B—C17B—C12B116.52 (18)
C17A—C16A—H16A120.1N1B—C18B—C19B122.92 (19)
C16A—C17A—N1A123.4 (2)N1B—C18B—H18B118.5
C16A—C17A—C12A119.7 (2)C19B—C18B—H18B118.5
N1A—C17A—C12A116.89 (19)C18B—C19B—C28B119.29 (18)
N1A—C18A—C19A122.82 (19)C18B—C19B—C20B120.41 (19)
N1A—C18A—H18A118.6C28B—C19B—C20B120.25 (18)
C19A—C18A—H18A118.6C21B—C20B—C25B117.97 (19)
C18A—C19A—C28A118.90 (19)C21B—C20B—C19B123.24 (19)
C18A—C19A—C20A121.26 (19)C25B—C20B—C19B118.78 (19)
C28A—C19A—C20A119.81 (19)C22B—C21B—C20B121.1 (2)
C25A—C20A—C21A117.3 (2)C22B—C21B—H21B119.5
C25A—C20A—C19A119.17 (19)C20B—C21B—H21B119.5
C21A—C20A—C19A123.5 (2)C21B—C22B—C23B120.6 (2)
C22A—C21A—C20A121.1 (2)C21B—C22B—H22B119.7
C22A—C21A—H21A119.4C23B—C22B—H22B119.7
C20A—C21A—H21A119.4C24B—C23B—C22B119.3 (2)
C21A—C22A—C23A120.9 (2)C24B—C23B—H23B120.3
C21A—C22A—H22A119.5C22B—C23B—H23B120.3
C23A—C22A—H22A119.5C23B—C24B—C25B121.1 (2)
C24A—C23A—C22A119.4 (2)C23B—C24B—H24B119.4
C24A—C23A—H23A120.3C25B—C24B—H24B119.4
C22A—C23A—H23A120.3C24B—C25B—C20B119.9 (2)
C23A—C24A—C25A120.7 (2)C24B—C25B—C26B120.6 (2)
C23A—C24A—H24A119.6C20B—C25B—C26B119.5 (2)
C25A—C24A—H24A119.6C27B—C26B—C25B122.5 (2)
C20A—C25A—C24A120.5 (2)C27B—C26B—H26B118.7
C20A—C25A—C26A119.5 (2)C25B—C26B—H26B118.7
C24A—C25A—C26A120.0 (2)C26B—C27B—C28B121.5 (2)
C27A—C26A—C25A121.8 (2)C26B—C27B—H27B119.3
C27A—C26A—H26A119.1C28B—C27B—H27B119.3
C25A—C26A—H26A119.1O1B—C28B—C27B120.1 (2)
C26A—C27A—C28A121.6 (2)O1B—C28B—C19B122.39 (19)
C26A—C27A—H27A119.2C27B—C28B—C19B117.47 (19)
C28A—C27A—H27A119.2C29—O3—HO3106 (2)
O1A—C28A—C27A119.6 (2)O3—C29—H29A109.5
O1A—C28A—C19A122.4 (2)O3—C29—H29B109.5
C27A—C28A—C19A118.0 (2)H29A—C29—H29B109.5
C1B—O2B—H2OB104 (3)O3—C29—H29C109.5
C18B—N1B—C17B127.03 (18)H29A—C29—H29C109.5
C18B—N1B—H1NB111.8 (17)H29B—C29—H29C109.5
C17B—N1B—H1NB121.2 (17)
O2A—C1A—C2A—C3A179.7 (2)O2B—C1B—C2B—C3B179.0 (2)
C10A—C1A—C2A—C3A1.1 (3)C10B—C1B—C2B—C3B0.3 (3)
C1A—C2A—C3A—C4A1.2 (3)C1B—C2B—C3B—C4B1.0 (4)
C2A—C3A—C4A—C5A178.4 (2)C2B—C3B—C4B—C9B0.3 (3)
C2A—C3A—C4A—C9A0.9 (3)C2B—C3B—C4B—C5B179.8 (2)
C3A—C4A—C5A—C6A178.2 (2)C9B—C4B—C5B—C6B2.3 (3)
C9A—C4A—C5A—C6A1.1 (3)C3B—C4B—C5B—C6B177.3 (2)
C4A—C5A—C6A—C7A0.0 (4)C4B—C5B—C6B—C7B1.1 (3)
C5A—C6A—C7A—C8A0.8 (4)C5B—C6B—C7B—C8B0.5 (3)
C6A—C7A—C8A—C9A0.5 (3)C6B—C7B—C8B—C9B0.8 (3)
C7A—C8A—C9A—C4A0.7 (3)C7B—C8B—C9B—C4B0.5 (3)
C7A—C8A—C9A—C10A179.9 (2)C7B—C8B—C9B—C10B179.72 (19)
C5A—C4A—C9A—C8A1.5 (3)C5B—C4B—C9B—C8B2.0 (3)
C3A—C4A—C9A—C8A177.9 (2)C3B—C4B—C9B—C8B177.56 (19)
C5A—C4A—C9A—C10A179.1 (2)C5B—C4B—C9B—C10B178.21 (19)
C3A—C4A—C9A—C10A1.6 (3)C3B—C4B—C9B—C10B2.2 (3)
O2A—C1A—C10A—C9A177.37 (19)O2B—C1B—C10B—C11B3.6 (3)
C2A—C1A—C10A—C9A3.5 (3)C2B—C1B—C10B—C11B175.73 (19)
O2A—C1A—C10A—C11A4.8 (3)O2B—C1B—C10B—C9B179.04 (18)
C2A—C1A—C10A—C11A174.3 (2)C2B—C1B—C10B—C9B1.6 (3)
C8A—C9A—C10A—C1A175.7 (2)C8B—C9B—C10B—C1B176.87 (19)
C4A—C9A—C10A—C1A3.7 (3)C4B—C9B—C10B—C1B2.9 (3)
C8A—C9A—C10A—C11A6.5 (3)C8B—C9B—C10B—C11B5.8 (3)
C4A—C9A—C10A—C11A174.12 (19)C4B—C9B—C10B—C11B174.49 (19)
C12A—N2A—C11A—C10A177.02 (19)C12B—N2B—C11B—C10B177.35 (18)
C1A—C10A—C11A—N2A11.3 (3)C1B—C10B—C11B—N2B10.2 (3)
C9A—C10A—C11A—N2A170.9 (2)C9B—C10B—C11B—N2B172.47 (19)
C11A—N2A—C12A—C13A44.3 (3)C11B—N2B—C12B—C13B43.6 (3)
C11A—N2A—C12A—C17A137.7 (2)C11B—N2B—C12B—C17B136.4 (2)
C17A—C12A—C13A—C14A0.5 (3)C17B—C12B—C13B—C14B0.8 (3)
N2A—C12A—C13A—C14A178.4 (2)N2B—C12B—C13B—C14B179.2 (2)
C12A—C13A—C14A—C15A0.2 (3)C12B—C13B—C14B—C15B0.9 (4)
C13A—C14A—C15A—C16A0.5 (3)C13B—C14B—C15B—C16B0.6 (4)
C14A—C15A—C16A—C17A0.1 (3)C14B—C15B—C16B—C17B0.1 (3)
C15A—C16A—C17A—N1A178.0 (2)C15B—C16B—C17B—N1B178.1 (2)
C15A—C16A—C17A—C12A0.6 (3)C15B—C16B—C17B—C12B0.0 (3)
C18A—N1A—C17A—C16A5.7 (3)C18B—N1B—C17B—C16B4.6 (3)
C18A—N1A—C17A—C12A176.9 (2)C18B—N1B—C17B—C12B177.23 (19)
C13A—C12A—C17A—C16A0.9 (3)C13B—C12B—C17B—C16B0.3 (3)
N2A—C12A—C17A—C16A178.92 (18)N2B—C12B—C17B—C16B179.69 (18)
C13A—C12A—C17A—N1A178.45 (19)C13B—C12B—C17B—N1B177.91 (19)
N2A—C12A—C17A—N1A3.5 (3)N2B—C12B—C17B—N1B2.1 (3)
C17A—N1A—C18A—C19A179.5 (2)C17B—N1B—C18B—C19B179.42 (19)
N1A—C18A—C19A—C28A0.0 (3)N1B—C18B—C19B—C28B1.4 (3)
N1A—C18A—C19A—C20A178.39 (19)N1B—C18B—C19B—C20B178.90 (18)
C18A—C19A—C20A—C25A178.51 (19)C18B—C19B—C20B—C21B5.2 (3)
C28A—C19A—C20A—C25A0.2 (3)C28B—C19B—C20B—C21B177.30 (19)
C18A—C19A—C20A—C21A1.4 (3)C18B—C19B—C20B—C25B175.36 (19)
C28A—C19A—C20A—C21A179.7 (2)C28B—C19B—C20B—C25B2.2 (3)
C25A—C20A—C21A—C22A1.7 (3)C25B—C20B—C21B—C22B1.1 (3)
C19A—C20A—C21A—C22A178.2 (2)C19B—C20B—C21B—C22B179.5 (2)
C20A—C21A—C22A—C23A1.0 (4)C20B—C21B—C22B—C23B0.4 (3)
C21A—C22A—C23A—C24A0.8 (4)C21B—C22B—C23B—C24B1.4 (3)
C22A—C23A—C24A—C25A1.8 (4)C22B—C23B—C24B—C25B0.9 (3)
C21A—C20A—C25A—C24A0.7 (3)C23B—C24B—C25B—C20B0.6 (3)
C19A—C20A—C25A—C24A179.2 (2)C23B—C24B—C25B—C26B178.0 (2)
C21A—C20A—C25A—C26A179.8 (2)C21B—C20B—C25B—C24B1.6 (3)
C19A—C20A—C25A—C26A0.3 (3)C19B—C20B—C25B—C24B178.90 (19)
C23A—C24A—C25A—C20A1.0 (3)C21B—C20B—C25B—C26B177.07 (19)
C23A—C24A—C25A—C26A178.4 (2)C19B—C20B—C25B—C26B2.4 (3)
C20A—C25A—C26A—C27A0.4 (3)C24B—C25B—C26B—C27B179.1 (2)
C24A—C25A—C26A—C27A179.0 (2)C20B—C25B—C26B—C27B0.5 (3)
C25A—C26A—C27A—C28A0.1 (4)C25B—C26B—C27B—C28B1.9 (3)
C26A—C27A—C28A—O1A178.8 (2)C26B—C27B—C28B—O1B176.9 (2)
C26A—C27A—C28A—C19A0.3 (3)C26B—C27B—C28B—C19B2.0 (3)
C18A—C19A—C28A—O1A0.3 (3)C18B—C19B—C28B—O1B1.3 (3)
C20A—C19A—C28A—O1A178.7 (2)C20B—C19B—C28B—O1B178.87 (19)
C18A—C19A—C28A—C27A178.84 (19)C18B—C19B—C28B—C27B177.57 (19)
C20A—C19A—C28A—C27A0.5 (3)C20B—C19B—C28B—C27B0.0 (3)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···Cg7iii0.932.673.575 (3)163
C29—H29C···Cg1iv0.962.783.668 (3)154
N1A—H1NA···O1A0.88 (4)1.78 (4)2.542 (2)143 (3)
N1B—H1NB···O1B0.91 (3)1.78 (3)2.560 (2)143 (2)
O2A—H2OA···N2A0.86 (3)1.84 (4)2.588 (2)145 (3)
O2B—H2OB···N2B0.95 (4)1.72 (4)2.600 (2)153 (3)
O3—HO3···O1A0.94 (5)1.84 (5)2.763 (3)168 (3)
Symmetry codes: (iii) x+1/2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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