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The title compound, 4C12H9N2+·2C10H5O8·C10H4O82−, contains singly and doubly deprotonated tetracarboxylic acids and the protonated form of 1,10-phenanthroline; the dianion is centrosymmetric. The crystal structure is stabilized by strong inter­molecular O—H...O and N—H...N hydrogen bonds, linking the ions to form a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024925/hk2066sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024925/hk2066Isup2.hkl
Contains datablock I

CCDC reference: 601605

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.108
  • Data-to-parameter ratio = 15.3

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 ............ 2.00 Ratio PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C13' - C15' ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C14' - C16' ... 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C13 - C15 ... 1.53 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C9 .. C10 .. 3.19 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C13' .. C14' .. 3.18 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C12 H9 N2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 C10 H4 O8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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.

1,10-phenanthrolinium–2,4,5-tricarboxybenzoate–2,5-dicarboxybenzene- 1,4-dicarboxylate (2/1/0.5) top
Crystal data top
4C12H9N2+·2C10H5O8·C10H4O82Z = 1
Mr = 1483.26F(000) = 766
Triclinic, P1Dx = 1.558 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6993 (8) ÅCell parameters from 999 reflections
b = 13.5070 (14) Åθ = 3–27°
c = 15.1719 (16) ŵ = 0.12 mm1
α = 107.075 (5)°T = 120 K
β = 101.375 (5)°Prism, colourless
γ = 104.174 (5)°0.22 × 0.18 × 0.16 mm
V = 1581.1 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
7598 independent reflections
Radiation source: fine-focus sealed tube4972 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 1111
Tmin = 0.973, Tmax = 0.980k = 1717
16402 measured reflectionsl = 2020
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)] = 0.049Hydrogen site location: structure-invariant direct methods
wR(F2) = 0.108H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.03P)2 + 0.6P]
where P = (Fo2 + 2Fc2)/3
7598 reflections(Δ/σ)max < 0.001
496 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

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
O10.15099 (18)0.10246 (13)0.29564 (10)0.0383 (4)
O20.09565 (16)0.09845 (11)0.22839 (9)0.0281 (3)
O30.25857 (18)0.01719 (12)0.27445 (9)0.0331 (3)
H3O0.21210.04230.24340.040*
O40.28069 (17)0.12797 (11)0.40680 (9)0.0276 (3)
N10.05058 (18)0.19388 (12)0.05109 (10)0.0207 (3)
H1N0.06950.15480.11100.025*
N20.21161 (18)0.04581 (12)0.04508 (11)0.0229 (3)
C10.0296 (2)0.26451 (15)0.05983 (14)0.0239 (4)
H1A0.05730.27470.11960.029*
C20.0727 (2)0.32322 (15)0.01781 (14)0.0251 (4)
H2A0.12840.37430.01190.030*
C30.0336 (2)0.30647 (15)0.10316 (13)0.0231 (4)
H3A0.06250.34650.15660.028*
C40.0486 (2)0.23092 (14)0.11275 (13)0.0208 (4)
C50.0884 (2)0.20693 (15)0.19835 (13)0.0250 (4)
H5A0.05890.24330.25310.030*
C60.1673 (2)0.13335 (15)0.20264 (13)0.0244 (4)
H6A0.19160.11840.26030.029*
C70.2153 (2)0.07728 (14)0.12222 (13)0.0213 (4)
C80.3000 (2)0.00095 (15)0.12388 (14)0.0253 (4)
H8A0.33190.01390.18100.030*
C90.3359 (2)0.05158 (15)0.04229 (14)0.0271 (4)
H9A0.39190.10380.04170.033*
C100.2883 (2)0.02668 (15)0.04057 (14)0.0255 (4)
H10A0.31270.06430.09690.031*
C110.1764 (2)0.09683 (14)0.03585 (13)0.0196 (4)
C120.0917 (2)0.17514 (14)0.03232 (12)0.0193 (4)
C130.0244 (2)0.08096 (15)0.30277 (13)0.0238 (4)
C140.2212 (2)0.05904 (15)0.36652 (13)0.0229 (4)
C150.0023 (2)0.03560 (14)0.40258 (12)0.0203 (4)
C160.1036 (2)0.02368 (14)0.42955 (13)0.0200 (4)
C170.1025 (2)0.05697 (14)0.52602 (13)0.0208 (4)
H17A0.17440.09670.54430.025*
O1'0.53032 (17)0.24732 (11)0.06090 (9)0.0272 (3)
O2'0.37344 (16)0.34451 (10)0.09649 (8)0.0246 (3)
H2'O0.31940.41270.06030.029*
O3'0.25511 (15)0.47862 (10)0.02270 (8)0.0233 (3)
O4'0.24143 (16)0.56247 (10)0.12264 (9)0.0257 (3)
O5'0.39276 (17)0.49155 (12)0.39640 (9)0.0329 (3)
O6'0.61320 (16)0.43736 (11)0.42788 (9)0.0282 (3)
H6'O0.62730.46670.49000.034*
O7'0.56500 (15)0.21816 (10)0.30675 (9)0.0258 (3)
H7'O0.61170.18900.33900.031*
O8'0.80675 (17)0.30206 (12)0.28891 (10)0.0345 (4)
N1'0.38113 (18)0.26601 (12)0.27893 (10)0.0210 (3)
H1'N0.36520.29360.21480.025*
N2'0.1385 (2)0.36040 (13)0.26673 (11)0.0266 (4)
C1'0.5006 (2)0.22064 (15)0.27945 (14)0.0254 (4)
H1'A0.55470.21250.22240.031*
C2'0.5470 (2)0.18507 (17)0.36293 (14)0.0297 (5)
H2'A0.63160.15190.36360.036*
C3'0.4687 (2)0.19861 (16)0.44442 (14)0.0293 (4)
H3'A0.50050.17550.50150.035*
C4'0.3427 (2)0.24589 (15)0.44430 (13)0.0231 (4)
C5'0.2555 (3)0.26249 (16)0.52678 (14)0.0290 (4)
H5'A0.28510.24200.58490.035*
C6'0.1329 (3)0.30642 (16)0.52331 (14)0.0299 (5)
H6'A0.07590.31490.57940.036*
C7'0.0863 (2)0.34098 (15)0.43606 (13)0.0247 (4)
C8'0.0394 (2)0.38789 (16)0.42853 (15)0.0321 (5)
H8'A0.10100.39710.48300.039*
C9'0.0732 (3)0.42042 (18)0.34209 (16)0.0347 (5)
H9'A0.15740.45310.33560.042*
C10'0.0191 (3)0.40468 (17)0.26306 (15)0.0314 (5)
H10B0.00590.42720.20360.038*
C11'0.1710 (2)0.32907 (14)0.35272 (13)0.0214 (4)
C12'0.2992 (2)0.27991 (14)0.35871 (12)0.0204 (4)
C13'0.4569 (2)0.31287 (14)0.03664 (12)0.0193 (4)
C14'0.2893 (2)0.49746 (14)0.06957 (12)0.0192 (4)
C15'0.4631 (2)0.35888 (14)0.06966 (12)0.0176 (4)
C16'0.3898 (2)0.43517 (14)0.11272 (12)0.0181 (4)
C17'0.4065 (2)0.46091 (14)0.21110 (12)0.0188 (4)
H17B0.35760.51210.24110.023*
C18'0.4910 (2)0.41536 (14)0.26686 (12)0.0190 (4)
C19'0.5665 (2)0.34145 (14)0.22473 (12)0.0193 (4)
C20'0.5510 (2)0.31545 (14)0.12732 (12)0.0199 (4)
H20A0.60260.26560.09830.024*
C21'0.4972 (2)0.45047 (14)0.37017 (13)0.0208 (4)
C22'0.6605 (2)0.28631 (15)0.27840 (12)0.0220 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0379 (9)0.0644 (11)0.0269 (8)0.0333 (8)0.0148 (7)0.0192 (8)
O20.0324 (8)0.0355 (8)0.0199 (7)0.0181 (6)0.0058 (6)0.0103 (6)
O30.0438 (9)0.0417 (9)0.0197 (7)0.0277 (7)0.0058 (6)0.0100 (6)
O40.0354 (8)0.0325 (8)0.0228 (7)0.0211 (6)0.0083 (6)0.0129 (6)
N10.0226 (8)0.0208 (8)0.0190 (8)0.0073 (6)0.0055 (6)0.0079 (6)
N20.0201 (8)0.0222 (8)0.0252 (8)0.0065 (6)0.0064 (7)0.0072 (7)
C10.0225 (10)0.0239 (10)0.0277 (10)0.0080 (8)0.0043 (8)0.0141 (8)
C20.0234 (10)0.0208 (9)0.0330 (11)0.0091 (8)0.0079 (8)0.0108 (8)
C30.0213 (9)0.0219 (10)0.0252 (10)0.0077 (8)0.0078 (8)0.0059 (8)
C40.0183 (9)0.0192 (9)0.0222 (9)0.0048 (7)0.0032 (7)0.0064 (8)
C50.0257 (10)0.0254 (10)0.0201 (10)0.0067 (8)0.0059 (8)0.0046 (8)
C60.0268 (10)0.0244 (10)0.0187 (9)0.0043 (8)0.0027 (8)0.0088 (8)
C70.0175 (9)0.0202 (9)0.0219 (9)0.0044 (7)0.0003 (7)0.0066 (8)
C80.0217 (10)0.0238 (10)0.0293 (11)0.0067 (8)0.0018 (8)0.0121 (8)
C90.0214 (10)0.0217 (10)0.0393 (12)0.0098 (8)0.0062 (9)0.0119 (9)
C100.0220 (10)0.0240 (10)0.0293 (11)0.0082 (8)0.0084 (8)0.0066 (8)
C110.0164 (9)0.0186 (9)0.0228 (9)0.0044 (7)0.0039 (7)0.0084 (8)
C120.0185 (9)0.0189 (9)0.0201 (9)0.0048 (7)0.0048 (7)0.0082 (7)
C130.0286 (10)0.0257 (10)0.0224 (10)0.0123 (8)0.0083 (8)0.0125 (8)
C140.0279 (10)0.0223 (10)0.0216 (10)0.0111 (8)0.0065 (8)0.0103 (8)
C150.0225 (9)0.0220 (9)0.0193 (9)0.0085 (8)0.0063 (7)0.0104 (8)
C160.0224 (9)0.0204 (9)0.0208 (9)0.0084 (7)0.0067 (7)0.0109 (8)
C170.0236 (9)0.0219 (9)0.0217 (9)0.0107 (8)0.0073 (8)0.0111 (8)
O1'0.0374 (8)0.0302 (7)0.0214 (7)0.0203 (6)0.0112 (6)0.0103 (6)
O2'0.0305 (7)0.0316 (7)0.0169 (6)0.0181 (6)0.0068 (5)0.0098 (6)
O3'0.0280 (7)0.0288 (7)0.0183 (7)0.0150 (6)0.0063 (5)0.0112 (6)
O4'0.0325 (8)0.0285 (7)0.0231 (7)0.0180 (6)0.0097 (6)0.0111 (6)
O5'0.0387 (8)0.0515 (9)0.0213 (7)0.0307 (7)0.0130 (6)0.0148 (7)
O6'0.0325 (8)0.0400 (8)0.0155 (6)0.0207 (6)0.0051 (6)0.0086 (6)
O7'0.0271 (7)0.0299 (7)0.0282 (7)0.0136 (6)0.0057 (6)0.0192 (6)
O8'0.0255 (8)0.0551 (10)0.0385 (8)0.0213 (7)0.0134 (6)0.0293 (8)
N1'0.0248 (8)0.0244 (8)0.0158 (7)0.0113 (7)0.0066 (6)0.0068 (6)
N2'0.0314 (9)0.0316 (9)0.0253 (9)0.0181 (8)0.0121 (7)0.0129 (7)
C1'0.0252 (10)0.0288 (10)0.0238 (10)0.0124 (8)0.0054 (8)0.0094 (8)
C2'0.0294 (11)0.0373 (12)0.0273 (11)0.0197 (9)0.0115 (9)0.0089 (9)
C3'0.0331 (11)0.0347 (11)0.0242 (10)0.0147 (9)0.0140 (9)0.0095 (9)
C4'0.0265 (10)0.0231 (10)0.0182 (9)0.0079 (8)0.0066 (8)0.0052 (8)
C5'0.0369 (12)0.0303 (11)0.0188 (10)0.0103 (9)0.0076 (8)0.0082 (8)
C6'0.0358 (12)0.0297 (11)0.0204 (10)0.0092 (9)0.0008 (8)0.0094 (8)
C7'0.0247 (10)0.0232 (10)0.0241 (10)0.0064 (8)0.0016 (8)0.0104 (8)
C8'0.0293 (11)0.0338 (11)0.0342 (12)0.0142 (9)0.0021 (9)0.0148 (10)
C9'0.0319 (12)0.0395 (12)0.0426 (13)0.0228 (10)0.0137 (10)0.0176 (11)
C10'0.0341 (12)0.0365 (12)0.0339 (11)0.0203 (10)0.0156 (9)0.0163 (10)
C11'0.0223 (9)0.0206 (9)0.0218 (9)0.0074 (8)0.0070 (8)0.0077 (8)
C12'0.0216 (9)0.0206 (9)0.0172 (9)0.0058 (7)0.0036 (7)0.0064 (7)
C13'0.0196 (9)0.0220 (9)0.0177 (9)0.0077 (8)0.0049 (7)0.0087 (7)
C14'0.0193 (9)0.0205 (9)0.0190 (9)0.0060 (7)0.0053 (7)0.0095 (8)
C15'0.0174 (9)0.0193 (9)0.0165 (9)0.0048 (7)0.0048 (7)0.0083 (7)
C16'0.0159 (9)0.0199 (9)0.0199 (9)0.0045 (7)0.0051 (7)0.0101 (7)
C17'0.0192 (9)0.0188 (9)0.0199 (9)0.0074 (7)0.0067 (7)0.0075 (7)
C18'0.0204 (9)0.0206 (9)0.0168 (9)0.0071 (7)0.0062 (7)0.0071 (7)
C19'0.0183 (9)0.0234 (9)0.0188 (9)0.0084 (7)0.0052 (7)0.0098 (8)
C20'0.0214 (9)0.0219 (9)0.0189 (9)0.0090 (8)0.0078 (7)0.0082 (8)
C21'0.0233 (9)0.0220 (9)0.0197 (9)0.0096 (8)0.0060 (8)0.0096 (8)
C22'0.0273 (10)0.0268 (10)0.0159 (9)0.0146 (8)0.0067 (8)0.0084 (8)
Geometric parameters (Å, º) top
O1—C131.222 (2)O5'—C21'1.245 (2)
O2—C131.295 (2)O6'—C21'1.283 (2)
O3—C141.282 (2)O6'—H6'O0.8781
O3—H3O1.0210O7'—C22'1.312 (2)
O4—C141.239 (2)O7'—H7'O0.8200
N1—C11.333 (2)O8'—C22'1.207 (2)
N1—C121.359 (2)N1'—C1'1.330 (2)
N1—H1N0.9756N1'—C12'1.366 (2)
N2—C101.322 (2)N1'—H1'N0.9854
N2—C111.353 (2)N2'—C10'1.322 (2)
C1—C21.389 (3)N2'—C11'1.357 (2)
C1—H1A0.9500C1'—C2'1.392 (3)
C2—C31.371 (3)C1'—H1'A0.9500
C2—H2A0.9500C2'—C3'1.374 (3)
C3—C41.406 (2)C2'—H2'A0.9500
C3—H3A0.9500C3'—C4'1.397 (3)
C4—C121.406 (3)C3'—H3'A0.9500
C4—C51.427 (2)C4'—C12'1.404 (2)
C5—C61.348 (3)C4'—C5'1.437 (3)
C5—H5A0.9500C5'—C6'1.344 (3)
C6—C71.431 (3)C5'—H5'A0.9500
C6—H6A0.9500C6'—C7'1.441 (3)
C7—C111.405 (2)C6'—H6'A0.9500
C7—C81.410 (3)C7'—C8'1.399 (3)
C8—C91.371 (3)C7'—C11'1.406 (2)
C8—H8A0.9500C8'—C9'1.370 (3)
C9—C101.406 (3)C8'—H8'A0.9500
C9—H9A0.9500C9'—C10'1.408 (3)
C10—H10A0.9500C9'—H9'A0.9500
C11—C121.437 (2)C10'—H10B0.9500
C13—C151.528 (3)C11'—C12'1.435 (2)
C14—C161.520 (2)C13'—C15'1.533 (2)
C15—C17i1.397 (2)C14'—C16'1.535 (2)
C15—C161.406 (2)C15'—C20'1.397 (2)
C16—C171.396 (2)C15'—C16'1.409 (2)
C17—C15i1.397 (2)C16'—C17'1.398 (2)
C17—H17A0.9500C17'—C18'1.384 (2)
O1'—C13'1.227 (2)C17'—H17B0.9500
O2'—C13'1.286 (2)C18'—C19'1.396 (2)
O2'—H2'O1.1788C18'—C21'1.484 (2)
O3'—C14'1.305 (2)C19'—C20'1.385 (2)
O3'—H2'O1.2249C19'—C22'1.510 (2)
O4'—C14'1.220 (2)C20'—H20A0.9500
C13—O2—H3O117.3N1'—C1'—H1'A119.8
C14—O3—H3O119.5C2'—C1'—H1'A119.8
C1—N1—C12122.25 (16)C3'—C2'—C1'118.96 (18)
C1—N1—H1N113.2C3'—C2'—H2'A120.5
C12—N1—H1N124.5C1'—C2'—H2'A120.5
C10—N2—C11116.52 (16)C2'—C3'—C4'120.77 (18)
N1—C1—C2120.43 (17)C2'—C3'—H3'A119.6
N1—C1—H1A119.8C4'—C3'—H3'A119.6
C2—C1—H1A119.8C3'—C4'—C12'118.34 (17)
C3—C2—C1119.08 (17)C3'—C4'—C5'123.77 (17)
C3—C2—H2A120.5C12'—C4'—C5'117.89 (17)
C1—C2—H2A120.5C6'—C5'—C4'121.35 (18)
C2—C3—C4120.97 (17)C6'—C5'—H5'A119.3
C2—C3—H3A119.5C4'—C5'—H5'A119.3
C4—C3—H3A119.5C5'—C6'—C7'121.24 (18)
C3—C4—C12117.51 (16)C5'—C6'—H6'A119.4
C3—C4—C5123.95 (17)C7'—C6'—H6'A119.4
C12—C4—C5118.54 (16)C8'—C7'—C11'117.03 (18)
C6—C5—C4120.90 (17)C8'—C7'—C6'123.44 (17)
C6—C5—H5A119.5C11'—C7'—C6'119.53 (17)
C4—C5—H5A119.5C9'—C8'—C7'119.49 (18)
C5—C6—C7121.45 (17)C9'—C8'—H8'A120.3
C5—C6—H6A119.3C7'—C8'—H8'A120.3
C7—C6—H6A119.3C8'—C9'—C10'118.87 (19)
C11—C7—C8116.82 (17)C8'—C9'—H9'A120.6
C11—C7—C6119.76 (16)C10'—C9'—H9'A120.6
C8—C7—C6123.42 (17)N2'—C10'—C9'123.85 (19)
C9—C8—C7119.33 (18)N2'—C10'—H10B118.1
C9—C8—H8A120.3C9'—C10'—H10B118.1
C7—C8—H8A120.3N2'—C11'—C7'124.18 (17)
C8—C9—C10118.76 (17)N2'—C11'—C12'117.61 (16)
C8—C9—H9A120.6C7'—C11'—C12'118.21 (16)
C10—C9—H9A120.6N1'—C12'—C4'119.13 (17)
N2—C10—C9124.12 (18)N1'—C12'—C11'119.12 (16)
N2—C10—H10A117.9C4'—C12'—C11'121.75 (16)
C9—C10—H10A117.9O1'—C13'—O2'123.03 (16)
N2—C11—C7124.41 (16)O1'—C13'—C15'118.84 (15)
N2—C11—C12117.49 (16)O2'—C13'—C15'118.13 (15)
C7—C11—C12118.10 (16)O4'—C14'—O3'121.63 (16)
N1—C12—C4119.75 (16)O4'—C14'—C16'118.86 (15)
N1—C12—C11119.01 (16)O3'—C14'—C16'119.50 (15)
C4—C12—C11121.24 (16)C20'—C15'—C16'118.70 (16)
O1—C13—O2122.52 (17)C20'—C15'—C13'113.24 (15)
O1—C13—C15119.41 (16)C16'—C15'—C13'128.04 (15)
O2—C13—C15118.03 (16)C17'—C16'—C15'117.46 (15)
O4—C14—O3121.48 (16)C17'—C16'—C14'111.69 (15)
O4—C14—C16118.01 (16)C15'—C16'—C14'130.85 (15)
O3—C14—C16120.50 (16)C18'—C17'—C16'123.14 (17)
C17i—C15—C16117.95 (16)C18'—C17'—H17B118.4
C17i—C15—C13113.96 (16)C16'—C17'—H17B118.4
C16—C15—C13128.09 (16)C17'—C18'—C19'119.46 (16)
C17—C16—C15117.82 (16)C17'—C18'—C21'116.78 (16)
C17—C16—C14114.08 (16)C19'—C18'—C21'123.76 (15)
C15—C16—C14128.10 (16)C20'—C19'—C18'117.91 (16)
C15i—C17—C16124.22 (17)C20'—C19'—C22'118.13 (16)
C15i—C17—H17A117.9C18'—C19'—C22'123.94 (15)
C16—C17—H17A117.9C19'—C20'—C15'123.31 (17)
C13'—O2'—H2'O114.2C19'—C20'—H20A118.3
C14'—O3'—H2'O109.8C15'—C20'—H20A118.3
C21'—O6'—H6'O117.7O5'—C21'—O6'123.74 (16)
C22'—O7'—H7'O116.1O5'—C21'—C18'119.22 (15)
C1'—N1'—C12'122.33 (16)O6'—C21'—C18'117.03 (16)
C1'—N1'—H1'N113.4O8'—C22'—O7'125.52 (17)
C12'—N1'—H1'N124.1O8'—C22'—C19'121.63 (17)
C10'—N2'—C11'116.59 (16)O7'—C22'—C19'112.78 (15)
N1'—C1'—C2'120.46 (17)
C12—N1—C1—C20.8 (3)C5'—C6'—C7'—C11'0.3 (3)
N1—C1—C2—C30.9 (3)C11'—C7'—C8'—C9'0.6 (3)
C1—C2—C3—C40.2 (3)C6'—C7'—C8'—C9'178.67 (19)
C2—C3—C4—C121.2 (3)C7'—C8'—C9'—C10'0.6 (3)
C2—C3—C4—C5177.98 (17)C11'—N2'—C10'—C9'0.1 (3)
C3—C4—C5—C6179.90 (18)C8'—C9'—C10'—N2'0.4 (3)
C12—C4—C5—C60.7 (3)C10'—N2'—C11'—C7'0.0 (3)
C4—C5—C6—C70.5 (3)C10'—N2'—C11'—C12'179.48 (17)
C5—C6—C7—C111.5 (3)C8'—C7'—C11'—N2'0.3 (3)
C5—C6—C7—C8179.05 (18)C6'—C7'—C11'—N2'178.99 (17)
C11—C7—C8—C91.7 (3)C8'—C7'—C11'—C12'179.22 (17)
C6—C7—C8—C9177.78 (17)C6'—C7'—C11'—C12'1.5 (3)
C7—C8—C9—C100.6 (3)C1'—N1'—C12'—C4'0.4 (3)
C11—N2—C10—C90.9 (3)C1'—N1'—C12'—C11'179.69 (17)
C8—C9—C10—N20.7 (3)C3'—C4'—C12'—N1'0.2 (3)
C10—N2—C11—C70.3 (3)C5'—C4'—C12'—N1'179.42 (16)
C10—N2—C11—C12179.40 (16)C3'—C4'—C12'—C11'179.92 (17)
C8—C7—C11—N21.5 (3)C5'—C4'—C12'—C11'0.5 (3)
C6—C7—C11—N2177.92 (16)N2'—C11'—C12'—N1'0.6 (2)
C8—C7—C11—C12179.32 (16)C7'—C11'—C12'—N1'178.97 (16)
C6—C7—C11—C121.2 (2)N2'—C11'—C12'—C4'179.35 (17)
C1—N1—C12—C40.3 (3)C7'—C11'—C12'—C4'1.1 (3)
C1—N1—C12—C11179.29 (16)O1'—C13'—C15'—C20'2.1 (2)
C3—C4—C12—N11.3 (2)O2'—C13'—C15'—C20'177.39 (15)
C5—C4—C12—N1177.93 (16)O1'—C13'—C15'—C16'179.26 (17)
C3—C4—C12—C11179.77 (16)O2'—C13'—C15'—C16'1.2 (3)
C5—C4—C12—C111.0 (3)C20'—C15'—C16'—C17'1.5 (2)
N2—C11—C12—N10.3 (2)C13'—C15'—C16'—C17'177.05 (16)
C7—C11—C12—N1178.91 (15)C20'—C15'—C16'—C14'179.06 (17)
N2—C11—C12—C4179.22 (16)C13'—C15'—C16'—C14'2.4 (3)
C7—C11—C12—C40.0 (2)O4'—C14'—C16'—C17'2.4 (2)
O1—C13—C15—C17i20.5 (3)O3'—C14'—C16'—C17'176.58 (15)
O2—C13—C15—C17i157.26 (17)O4'—C14'—C16'—C15'178.11 (17)
O1—C13—C15—C16159.18 (19)O3'—C14'—C16'—C15'2.9 (3)
O2—C13—C15—C1623.0 (3)C15'—C16'—C17'—C18'0.1 (3)
C17i—C15—C16—C170.3 (3)C14'—C16'—C17'—C18'179.68 (16)
C13—C15—C16—C17179.97 (17)C16'—C17'—C18'—C19'1.2 (3)
C17i—C15—C16—C14178.73 (17)C16'—C17'—C18'—C21'179.67 (16)
C13—C15—C16—C141.0 (3)C17'—C18'—C19'—C20'1.0 (3)
O4—C14—C16—C1712.5 (2)C21'—C18'—C19'—C20'179.88 (16)
O3—C14—C16—C17166.62 (17)C17'—C18'—C19'—C22'179.53 (16)
O4—C14—C16—C15166.58 (18)C21'—C18'—C19'—C22'1.4 (3)
O3—C14—C16—C1514.3 (3)C18'—C19'—C20'—C15'0.4 (3)
C15—C16—C17—C15i0.3 (3)C22'—C19'—C20'—C15'178.22 (16)
C14—C16—C17—C15i178.85 (17)C16'—C15'—C20'—C19'1.7 (3)
C12'—N1'—C1'—C2'0.0 (3)C13'—C15'—C20'—C19'177.07 (16)
N1'—C1'—C2'—C3'0.7 (3)C17'—C18'—C21'—O5'20.3 (3)
C1'—C2'—C3'—C4'0.9 (3)C19'—C18'—C21'—O5'160.61 (18)
C2'—C3'—C4'—C12'0.5 (3)C17'—C18'—C21'—O6'158.96 (16)
C2'—C3'—C4'—C5'179.96 (19)C19'—C18'—C21'—O6'20.2 (3)
C3'—C4'—C5'—C6'178.65 (19)C20'—C19'—C22'—O8'65.0 (2)
C12'—C4'—C5'—C6'1.8 (3)C18'—C19'—C22'—O8'116.5 (2)
C4'—C5'—C6'—C7'1.4 (3)C20'—C19'—C22'—O7'112.10 (18)
C5'—C6'—C7'—C8'179.50 (19)C18'—C19'—C22'—O7'66.4 (2)
Symmetry code: (i) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O31.181.232.402 (2)176
N1—H1N···O20.981.802.771 (2)171
O6—H6O···O5ii0.881.712.570 (2)167
O7—H7O···O4iii0.821.762.583 (2)178
O2—H3O···O31.421.022.402 (2)159
N1—H1N···O20.991.702.678 (2)170
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1, y, z.
 

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