A proton-transfer compound: 1,10-phenanthrolinium–2,4,5-tricarboxy­benzoate–2,5-dicarboxy­benzene-1,4-dicarboxyl­ate (4/2/1)

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.

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

No syntax errors found



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

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)

Crystal data

4C12H9N2^+·2C10H5O8^−·C10H4O8^2^−	Z = 1
Mr = 1483.26	F(000) = 766
Triclinic, P1	Dx = 1.558 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6993 (8) Å	Cell parameters from 999 reflections
b = 13.5070 (14) Å	θ = 3–27°
c = 15.1719 (16) Å	µ = 0.12 mm^−1
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) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	7598 independent reflections
Radiation source: fine-focus sealed tube	4972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.973, Tmax = 0.980	k = −17→17
16402 measured reflections	l = −20→20

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)] = 0.049	Hydrogen site location: structure-invariant direct methods
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.6P] where P = (Fo^2 + 2Fc^2)/3
7598 reflections	(Δ/σ)max < 0.001
496 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.29 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
O1	−0.15099 (18)	0.10246 (13)	−0.29564 (10)	0.0383 (4)
O2	0.09565 (16)	0.09845 (11)	−0.22839 (9)	0.0281 (3)
O3	0.25857 (18)	−0.01719 (12)	−0.27445 (9)	0.0331 (3)
H3O	0.2121	0.0423	−0.2434	0.040*
O4	0.28069 (17)	−0.12797 (11)	−0.40680 (9)	0.0276 (3)
N1	0.05058 (18)	0.19388 (12)	−0.05109 (10)	0.0207 (3)
H1N	0.0695	0.1548	−0.1110	0.025*
N2	0.21161 (18)	0.04581 (12)	−0.04508 (11)	0.0229 (3)
C1	−0.0296 (2)	0.26451 (15)	−0.05983 (14)	0.0239 (4)
H1A	−0.0573	0.2747	−0.1196	0.029*
C2	−0.0727 (2)	0.32322 (15)	0.01781 (14)	0.0251 (4)
H2A	−0.1284	0.3743	0.0119	0.030*
C3	−0.0336 (2)	0.30647 (15)	0.10316 (13)	0.0231 (4)
H3A	−0.0625	0.3465	0.1566	0.028*
C4	0.0486 (2)	0.23092 (14)	0.11275 (13)	0.0208 (4)
C5	0.0884 (2)	0.20693 (15)	0.19835 (13)	0.0250 (4)
H5A	0.0589	0.2433	0.2531	0.030*
C6	0.1673 (2)	0.13335 (15)	0.20264 (13)	0.0244 (4)
H6A	0.1916	0.1184	0.2603	0.029*
C7	0.2153 (2)	0.07728 (14)	0.12222 (13)	0.0213 (4)
C8	0.3000 (2)	0.00095 (15)	0.12388 (14)	0.0253 (4)
H8A	0.3319	−0.0139	0.1810	0.030*
C9	0.3359 (2)	−0.05158 (15)	0.04229 (14)	0.0271 (4)
H9A	0.3919	−0.1038	0.0417	0.033*
C10	0.2883 (2)	−0.02668 (15)	−0.04057 (14)	0.0255 (4)
H10A	0.3127	−0.0643	−0.0969	0.031*
C11	0.1764 (2)	0.09683 (14)	0.03585 (13)	0.0196 (4)
C12	0.0917 (2)	0.17514 (14)	0.03232 (12)	0.0193 (4)
C13	−0.0244 (2)	0.08096 (15)	−0.30277 (13)	0.0238 (4)
C14	0.2212 (2)	−0.05904 (15)	−0.36652 (13)	0.0229 (4)
C15	−0.0023 (2)	0.03560 (14)	−0.40258 (12)	0.0203 (4)
C16	0.1036 (2)	−0.02368 (14)	−0.42955 (13)	0.0200 (4)
C17	0.1025 (2)	−0.05697 (14)	−0.52602 (13)	0.0208 (4)
H17A	0.1744	−0.0967	−0.5443	0.025*
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'O	0.3194	0.4127	−0.0603	0.029*
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'O	0.6273	0.4667	0.4900	0.034*
O7'	0.56500 (15)	0.21816 (10)	0.30675 (9)	0.0258 (3)
H7'O	0.6117	0.1890	0.3390	0.031*
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'N	0.3652	0.2936	−0.2148	0.025*
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'A	0.5547	0.2125	−0.2224	0.031*
C2'	0.5470 (2)	0.18507 (17)	−0.36293 (14)	0.0297 (5)
H2'A	0.6316	0.1519	−0.3636	0.036*
C3'	0.4687 (2)	0.19861 (16)	−0.44442 (14)	0.0293 (4)
H3'A	0.5005	0.1755	−0.5015	0.035*
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'A	0.2851	0.2420	−0.5849	0.035*
C6'	0.1329 (3)	0.30642 (16)	−0.52331 (14)	0.0299 (5)
H6'A	0.0759	0.3149	−0.5794	0.036*
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'A	−0.1010	0.3971	−0.4830	0.039*
C9'	−0.0732 (3)	0.42042 (18)	−0.34209 (16)	0.0347 (5)
H9'A	−0.1574	0.4531	−0.3356	0.042*
C10'	0.0191 (3)	0.40468 (17)	−0.26306 (15)	0.0314 (5)
H10B	−0.0059	0.4272	−0.2036	0.038*
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)
H17B	0.3576	0.5121	0.2411	0.023*
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)
H20A	0.6026	0.2656	0.0983	0.024*
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0379 (9)	0.0644 (11)	0.0269 (8)	0.0333 (8)	0.0148 (7)	0.0192 (8)
O2	0.0324 (8)	0.0355 (8)	0.0199 (7)	0.0181 (6)	0.0058 (6)	0.0103 (6)
O3	0.0438 (9)	0.0417 (9)	0.0197 (7)	0.0277 (7)	0.0058 (6)	0.0100 (6)
O4	0.0354 (8)	0.0325 (8)	0.0228 (7)	0.0211 (6)	0.0083 (6)	0.0129 (6)
N1	0.0226 (8)	0.0208 (8)	0.0190 (8)	0.0073 (6)	0.0055 (6)	0.0079 (6)
N2	0.0201 (8)	0.0222 (8)	0.0252 (8)	0.0065 (6)	0.0064 (7)	0.0072 (7)
C1	0.0225 (10)	0.0239 (10)	0.0277 (10)	0.0080 (8)	0.0043 (8)	0.0141 (8)
C2	0.0234 (10)	0.0208 (9)	0.0330 (11)	0.0091 (8)	0.0079 (8)	0.0108 (8)
C3	0.0213 (9)	0.0219 (10)	0.0252 (10)	0.0077 (8)	0.0078 (8)	0.0059 (8)
C4	0.0183 (9)	0.0192 (9)	0.0222 (9)	0.0048 (7)	0.0032 (7)	0.0064 (8)
C5	0.0257 (10)	0.0254 (10)	0.0201 (10)	0.0067 (8)	0.0059 (8)	0.0046 (8)
C6	0.0268 (10)	0.0244 (10)	0.0187 (9)	0.0043 (8)	0.0027 (8)	0.0088 (8)
C7	0.0175 (9)	0.0202 (9)	0.0219 (9)	0.0044 (7)	0.0003 (7)	0.0066 (8)
C8	0.0217 (10)	0.0238 (10)	0.0293 (11)	0.0067 (8)	0.0018 (8)	0.0121 (8)
C9	0.0214 (10)	0.0217 (10)	0.0393 (12)	0.0098 (8)	0.0062 (9)	0.0119 (9)
C10	0.0220 (10)	0.0240 (10)	0.0293 (11)	0.0082 (8)	0.0084 (8)	0.0066 (8)
C11	0.0164 (9)	0.0186 (9)	0.0228 (9)	0.0044 (7)	0.0039 (7)	0.0084 (8)
C12	0.0185 (9)	0.0189 (9)	0.0201 (9)	0.0048 (7)	0.0048 (7)	0.0082 (7)
C13	0.0286 (10)	0.0257 (10)	0.0224 (10)	0.0123 (8)	0.0083 (8)	0.0125 (8)
C14	0.0279 (10)	0.0223 (10)	0.0216 (10)	0.0111 (8)	0.0065 (8)	0.0103 (8)
C15	0.0225 (9)	0.0220 (9)	0.0193 (9)	0.0085 (8)	0.0063 (7)	0.0104 (8)
C16	0.0224 (9)	0.0204 (9)	0.0208 (9)	0.0084 (7)	0.0067 (7)	0.0109 (8)
C17	0.0236 (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)

O1—C13	1.222 (2)	O5'—C21'	1.245 (2)
O2—C13	1.295 (2)	O6'—C21'	1.283 (2)
O3—C14	1.282 (2)	O6'—H6'O	0.8781
O3—H3O	1.0210	O7'—C22'	1.312 (2)
O4—C14	1.239 (2)	O7'—H7'O	0.8200
N1—C1	1.333 (2)	O8'—C22'	1.207 (2)
N1—C12	1.359 (2)	N1'—C1'	1.330 (2)
N1—H1N	0.9756	N1'—C12'	1.366 (2)
N2—C10	1.322 (2)	N1'—H1'N	0.9854
N2—C11	1.353 (2)	N2'—C10'	1.322 (2)
C1—C2	1.389 (3)	N2'—C11'	1.357 (2)
C1—H1A	0.9500	C1'—C2'	1.392 (3)
C2—C3	1.371 (3)	C1'—H1'A	0.9500
C2—H2A	0.9500	C2'—C3'	1.374 (3)
C3—C4	1.406 (2)	C2'—H2'A	0.9500
C3—H3A	0.9500	C3'—C4'	1.397 (3)
C4—C12	1.406 (3)	C3'—H3'A	0.9500
C4—C5	1.427 (2)	C4'—C12'	1.404 (2)
C5—C6	1.348 (3)	C4'—C5'	1.437 (3)
C5—H5A	0.9500	C5'—C6'	1.344 (3)
C6—C7	1.431 (3)	C5'—H5'A	0.9500
C6—H6A	0.9500	C6'—C7'	1.441 (3)
C7—C11	1.405 (2)	C6'—H6'A	0.9500
C7—C8	1.410 (3)	C7'—C8'	1.399 (3)
C8—C9	1.371 (3)	C7'—C11'	1.406 (2)
C8—H8A	0.9500	C8'—C9'	1.370 (3)
C9—C10	1.406 (3)	C8'—H8'A	0.9500
C9—H9A	0.9500	C9'—C10'	1.408 (3)
C10—H10A	0.9500	C9'—H9'A	0.9500
C11—C12	1.437 (2)	C10'—H10B	0.9500
C13—C15	1.528 (3)	C11'—C12'	1.435 (2)
C14—C16	1.520 (2)	C13'—C15'	1.533 (2)
C15—C17^i	1.397 (2)	C14'—C16'	1.535 (2)
C15—C16	1.406 (2)	C15'—C20'	1.397 (2)
C16—C17	1.396 (2)	C15'—C16'	1.409 (2)
C17—C15^i	1.397 (2)	C16'—C17'	1.398 (2)
C17—H17A	0.9500	C17'—C18'	1.384 (2)
O1'—C13'	1.227 (2)	C17'—H17B	0.9500
O2'—C13'	1.286 (2)	C18'—C19'	1.396 (2)
O2'—H2'O	1.1788	C18'—C21'	1.484 (2)
O3'—C14'	1.305 (2)	C19'—C20'	1.385 (2)
O3'—H2'O	1.2249	C19'—C22'	1.510 (2)
O4'—C14'	1.220 (2)	C20'—H20A	0.9500
C13—O2—H3O	117.3	N1'—C1'—H1'A	119.8
C14—O3—H3O	119.5	C2'—C1'—H1'A	119.8
C1—N1—C12	122.25 (16)	C3'—C2'—C1'	118.96 (18)
C1—N1—H1N	113.2	C3'—C2'—H2'A	120.5
C12—N1—H1N	124.5	C1'—C2'—H2'A	120.5
C10—N2—C11	116.52 (16)	C2'—C3'—C4'	120.77 (18)
N1—C1—C2	120.43 (17)	C2'—C3'—H3'A	119.6
N1—C1—H1A	119.8	C4'—C3'—H3'A	119.6
C2—C1—H1A	119.8	C3'—C4'—C12'	118.34 (17)
C3—C2—C1	119.08 (17)	C3'—C4'—C5'	123.77 (17)
C3—C2—H2A	120.5	C12'—C4'—C5'	117.89 (17)
C1—C2—H2A	120.5	C6'—C5'—C4'	121.35 (18)
C2—C3—C4	120.97 (17)	C6'—C5'—H5'A	119.3
C2—C3—H3A	119.5	C4'—C5'—H5'A	119.3
C4—C3—H3A	119.5	C5'—C6'—C7'	121.24 (18)
C3—C4—C12	117.51 (16)	C5'—C6'—H6'A	119.4
C3—C4—C5	123.95 (17)	C7'—C6'—H6'A	119.4
C12—C4—C5	118.54 (16)	C8'—C7'—C11'	117.03 (18)
C6—C5—C4	120.90 (17)	C8'—C7'—C6'	123.44 (17)
C6—C5—H5A	119.5	C11'—C7'—C6'	119.53 (17)
C4—C5—H5A	119.5	C9'—C8'—C7'	119.49 (18)
C5—C6—C7	121.45 (17)	C9'—C8'—H8'A	120.3
C5—C6—H6A	119.3	C7'—C8'—H8'A	120.3
C7—C6—H6A	119.3	C8'—C9'—C10'	118.87 (19)
C11—C7—C8	116.82 (17)	C8'—C9'—H9'A	120.6
C11—C7—C6	119.76 (16)	C10'—C9'—H9'A	120.6
C8—C7—C6	123.42 (17)	N2'—C10'—C9'	123.85 (19)
C9—C8—C7	119.33 (18)	N2'—C10'—H10B	118.1
C9—C8—H8A	120.3	C9'—C10'—H10B	118.1
C7—C8—H8A	120.3	N2'—C11'—C7'	124.18 (17)
C8—C9—C10	118.76 (17)	N2'—C11'—C12'	117.61 (16)
C8—C9—H9A	120.6	C7'—C11'—C12'	118.21 (16)
C10—C9—H9A	120.6	N1'—C12'—C4'	119.13 (17)
N2—C10—C9	124.12 (18)	N1'—C12'—C11'	119.12 (16)
N2—C10—H10A	117.9	C4'—C12'—C11'	121.75 (16)
C9—C10—H10A	117.9	O1'—C13'—O2'	123.03 (16)
N2—C11—C7	124.41 (16)	O1'—C13'—C15'	118.84 (15)
N2—C11—C12	117.49 (16)	O2'—C13'—C15'	118.13 (15)
C7—C11—C12	118.10 (16)	O4'—C14'—O3'	121.63 (16)
N1—C12—C4	119.75 (16)	O4'—C14'—C16'	118.86 (15)
N1—C12—C11	119.01 (16)	O3'—C14'—C16'	119.50 (15)
C4—C12—C11	121.24 (16)	C20'—C15'—C16'	118.70 (16)
O1—C13—O2	122.52 (17)	C20'—C15'—C13'	113.24 (15)
O1—C13—C15	119.41 (16)	C16'—C15'—C13'	128.04 (15)
O2—C13—C15	118.03 (16)	C17'—C16'—C15'	117.46 (15)
O4—C14—O3	121.48 (16)	C17'—C16'—C14'	111.69 (15)
O4—C14—C16	118.01 (16)	C15'—C16'—C14'	130.85 (15)
O3—C14—C16	120.50 (16)	C18'—C17'—C16'	123.14 (17)
C17^i—C15—C16	117.95 (16)	C18'—C17'—H17B	118.4
C17^i—C15—C13	113.96 (16)	C16'—C17'—H17B	118.4
C16—C15—C13	128.09 (16)	C17'—C18'—C19'	119.46 (16)
C17—C16—C15	117.82 (16)	C17'—C18'—C21'	116.78 (16)
C17—C16—C14	114.08 (16)	C19'—C18'—C21'	123.76 (15)
C15—C16—C14	128.10 (16)	C20'—C19'—C18'	117.91 (16)
C15^i—C17—C16	124.22 (17)	C20'—C19'—C22'	118.13 (16)
C15^i—C17—H17A	117.9	C18'—C19'—C22'	123.94 (15)
C16—C17—H17A	117.9	C19'—C20'—C15'	123.31 (17)
C13'—O2'—H2'O	114.2	C19'—C20'—H20A	118.3
C14'—O3'—H2'O	109.8	C15'—C20'—H20A	118.3
C21'—O6'—H6'O	117.7	O5'—C21'—O6'	123.74 (16)
C22'—O7'—H7'O	116.1	O5'—C21'—C18'	119.22 (15)
C1'—N1'—C12'	122.33 (16)	O6'—C21'—C18'	117.03 (16)
C1'—N1'—H1'N	113.4	O8'—C22'—O7'	125.52 (17)
C12'—N1'—H1'N	124.1	O8'—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—C2	0.8 (3)	C5'—C6'—C7'—C11'	0.3 (3)
N1—C1—C2—C3	−0.9 (3)	C11'—C7'—C8'—C9'	0.6 (3)
C1—C2—C3—C4	−0.2 (3)	C6'—C7'—C8'—C9'	−178.67 (19)
C2—C3—C4—C12	1.2 (3)	C7'—C8'—C9'—C10'	−0.6 (3)
C2—C3—C4—C5	−177.98 (17)	C11'—N2'—C10'—C9'	−0.1 (3)
C3—C4—C5—C6	179.90 (18)	C8'—C9'—C10'—N2'	0.4 (3)
C12—C4—C5—C6	0.7 (3)	C10'—N2'—C11'—C7'	0.0 (3)
C4—C5—C6—C7	0.5 (3)	C10'—N2'—C11'—C12'	−179.48 (17)
C5—C6—C7—C11	−1.5 (3)	C8'—C7'—C11'—N2'	−0.3 (3)
C5—C6—C7—C8	179.05 (18)	C6'—C7'—C11'—N2'	178.99 (17)
C11—C7—C8—C9	−1.7 (3)	C8'—C7'—C11'—C12'	179.22 (17)
C6—C7—C8—C9	177.78 (17)	C6'—C7'—C11'—C12'	−1.5 (3)
C7—C8—C9—C10	0.6 (3)	C1'—N1'—C12'—C4'	−0.4 (3)
C11—N2—C10—C9	−0.9 (3)	C1'—N1'—C12'—C11'	179.69 (17)
C8—C9—C10—N2	0.7 (3)	C3'—C4'—C12'—N1'	0.2 (3)
C10—N2—C11—C7	−0.3 (3)	C5'—C4'—C12'—N1'	−179.42 (16)
C10—N2—C11—C12	−179.40 (16)	C3'—C4'—C12'—C11'	−179.92 (17)
C8—C7—C11—N2	1.5 (3)	C5'—C4'—C12'—C11'	0.5 (3)
C6—C7—C11—N2	−177.92 (16)	N2'—C11'—C12'—N1'	0.6 (2)
C8—C7—C11—C12	−179.32 (16)	C7'—C11'—C12'—N1'	−178.97 (16)
C6—C7—C11—C12	1.2 (2)	N2'—C11'—C12'—C4'	−179.35 (17)
C1—N1—C12—C4	0.3 (3)	C7'—C11'—C12'—C4'	1.1 (3)
C1—N1—C12—C11	179.29 (16)	O1'—C13'—C15'—C20'	−2.1 (2)
C3—C4—C12—N1	−1.3 (2)	O2'—C13'—C15'—C20'	177.39 (15)
C5—C4—C12—N1	177.93 (16)	O1'—C13'—C15'—C16'	179.26 (17)
C3—C4—C12—C11	179.77 (16)	O2'—C13'—C15'—C16'	−1.2 (3)
C5—C4—C12—C11	−1.0 (3)	C20'—C15'—C16'—C17'	−1.5 (2)
N2—C11—C12—N1	0.3 (2)	C13'—C15'—C16'—C17'	177.05 (16)
C7—C11—C12—N1	−178.91 (15)	C20'—C15'—C16'—C14'	179.06 (17)
N2—C11—C12—C4	179.22 (16)	C13'—C15'—C16'—C14'	−2.4 (3)
C7—C11—C12—C4	0.0 (2)	O4'—C14'—C16'—C17'	2.4 (2)
O1—C13—C15—C17^i	20.5 (3)	O3'—C14'—C16'—C17'	−176.58 (15)
O2—C13—C15—C17^i	−157.26 (17)	O4'—C14'—C16'—C15'	−178.11 (17)
O1—C13—C15—C16	−159.18 (19)	O3'—C14'—C16'—C15'	2.9 (3)
O2—C13—C15—C16	23.0 (3)	C15'—C16'—C17'—C18'	0.1 (3)
C17^i—C15—C16—C17	0.3 (3)	C14'—C16'—C17'—C18'	179.68 (16)
C13—C15—C16—C17	179.97 (17)	C16'—C17'—C18'—C19'	1.2 (3)
C17^i—C15—C16—C14	−178.73 (17)	C16'—C17'—C18'—C21'	−179.67 (16)
C13—C15—C16—C14	1.0 (3)	C17'—C18'—C19'—C20'	−1.0 (3)
O4—C14—C16—C17	−12.5 (2)	C21'—C18'—C19'—C20'	179.88 (16)
O3—C14—C16—C17	166.62 (17)	C17'—C18'—C19'—C22'	−179.53 (16)
O4—C14—C16—C15	166.58 (18)	C21'—C18'—C19'—C22'	1.4 (3)
O3—C14—C16—C15	−14.3 (3)	C18'—C19'—C20'—C15'	−0.4 (3)
C15—C16—C17—C15^i	−0.3 (3)	C22'—C19'—C20'—C15'	178.22 (16)
C14—C16—C17—C15^i	178.85 (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, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2′O···O3′	1.18	1.23	2.402 (2)	176
N1—H1N···O2	0.98	1.80	2.771 (2)	171
O6′—H6′O···O5′^ii	0.88	1.71	2.570 (2)	167
O7′—H7′O···O4^iii	0.82	1.76	2.583 (2)	178
O2—H3O···O3	1.42	1.02	2.402 (2)	159
N1′—H1′N···O2′	0.99	1.70	2.678 (2)	170

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