In the title compound, C14H19N4O3+·C5H7O4−, trimethoprim (TMP) is protonated. In the glutarate anion, one of the two carboxylic acid groups is deprotonated while the other exists as —COOH. The carboxyl group of the hydrogen glutarate ion makes a hydrogen-bonding pattern with N—H groups of the trimethoprim cation which is similar to the carboxylate group (of Asp-27 of DHFR)-trimethoprim cation interaction observed in trimethoprim–DHFR complexes. Two TMP cations and two hydrogen glutarate anions are arranged about an inversion center so that complementary DDAA arrays of quadruple hydrogen-bonding patterns are formed. The hydrogen glutarate ion bridges the 2-amino and 4-amino groups of TMP. There are also carboxyl–carboxylate hydrogen-bonding interactions involving a head-to-tail arrangement of hydrogen glutarate ions which leads to hydrogen-bonded supramolecular ribbons.
Supporting information
CCDC reference: 177221
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.140
- Data-to-parameter ratio = 8.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 70.90
From the CIF: _reflns_number_total 3203
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3958
Completeness (_total/calc) 80.92%
Alert A: < 85% complete (theta max?)
| Author response: Due to poor data we couldn't achieve more than 85%
|
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: PLATON.
2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium glutarate
top
Crystal data top
C14H19N4O3+·C5H7O4− | Z = 2 |
Mr = 422.44 | F(000) = 448 |
Triclinic, P1 | Dx = 1.367 Mg m−3 |
a = 12.017 (2) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 10.090 (3) Å | Cell parameters from 40 reflections |
c = 8.804 (4) Å | θ = 3.8–70.9° |
α = 84.430 (3)° | µ = 0.89 mm−1 |
β = 94.900 (3)° | T = 293 K |
γ = 104.590 (3)° | Thin plate, pale yellow |
V = 1026.1 (6) Å3 | 0.25 × 0.22 × 0.19 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 70.9°, θmin = 3.8° |
Graphite monochromator | h = −14→14 |
ω–2θ scans | k = −12→12 |
3203 measured reflections | l = 0→10 |
3203 independent reflections | 1 standard reflections every 100 min |
3201 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0866P)2 + 0.1793P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.048 | (Δ/σ)max < 0.001 |
wR(F2) = 0.140 | Δρmax = 0.21 e Å−3 |
S = 1.11 | Δρmin = −0.23 e Å−3 |
3203 reflections | Absolute structure: Flack (1983) |
363 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.45141 (13) | 0.87527 (15) | 0.73650 (15) | 0.0585 (5) | |
O2 | 0.59069 (12) | 0.78210 (15) | 0.57704 (17) | 0.0572 (5) | |
O3 | 0.52998 (13) | 0.71564 (16) | 0.29046 (16) | 0.0600 (5) | |
N1 | 0.05252 (14) | 0.82591 (17) | −0.10391 (17) | 0.0491 (5) | |
N2 | 0.06864 (17) | 0.98838 (19) | −0.31074 (18) | 0.0575 (6) | |
N3 | 0.15813 (15) | 1.05315 (17) | −0.07878 (18) | 0.0508 (5) | |
N4 | 0.24980 (19) | 1.1136 (2) | 0.1481 (2) | 0.0693 (7) | |
C2 | 0.09384 (17) | 0.9571 (2) | −0.1627 (2) | 0.0461 (6) | |
C4 | 0.18378 (17) | 1.0157 (2) | 0.0689 (2) | 0.0490 (6) | |
C5 | 0.14042 (16) | 0.8791 (2) | 0.1401 (2) | 0.0471 (6) | |
C6 | 0.07496 (17) | 0.7889 (2) | 0.0470 (2) | 0.0481 (6) | |
C7 | 0.15670 (17) | 0.8417 (3) | 0.3090 (2) | 0.0568 (7) | |
C8 | 0.27701 (15) | 0.83263 (19) | 0.37225 (19) | 0.0438 (5) | |
C9 | 0.30932 (16) | 0.86674 (19) | 0.5205 (2) | 0.0452 (6) | |
C10 | 0.41372 (16) | 0.84784 (18) | 0.5896 (2) | 0.0442 (5) | |
C11 | 0.48561 (15) | 0.79685 (18) | 0.5096 (2) | 0.0447 (5) | |
C12 | 0.45284 (16) | 0.76436 (19) | 0.3595 (2) | 0.0445 (6) | |
C13 | 0.34798 (16) | 0.78229 (19) | 0.2912 (2) | 0.0450 (6) | |
C14 | 0.3789 (2) | 0.9274 (3) | 0.8200 (2) | 0.0637 (8) | |
C15 | 0.5871 (3) | 0.6471 (3) | 0.6435 (4) | 0.0887 (11) | |
C16 | 0.5029 (2) | 0.6836 (3) | 0.1364 (3) | 0.0718 (9) | |
O4 | 0.07782 (16) | 0.22219 (17) | 0.46913 (16) | 0.0730 (6) | |
O5 | 0.08143 (15) | 0.37575 (17) | 0.27020 (15) | 0.0680 (6) | |
O6 | 0.27767 (17) | 0.4052 (2) | 1.00442 (19) | 0.0808 (7) | |
O7 | 0.14593 (17) | 0.5178 (2) | 1.01426 (18) | 0.0769 (7) | |
C17 | 0.21973 (17) | 0.47756 (18) | 0.9423 (2) | 0.0467 (6) | |
C18 | 0.2212 (2) | 0.5289 (2) | 0.7757 (2) | 0.0599 (7) | |
C19 | 0.1775 (2) | 0.4110 (2) | 0.6763 (2) | 0.0597 (7) | |
C20 | 0.1615 (2) | 0.4566 (2) | 0.5084 (2) | 0.0579 (7) | |
C21 | 0.10397 (17) | 0.3416 (2) | 0.4102 (2) | 0.0514 (6) | |
H1 | 0.01188 | 0.76561 | −0.16215 | 0.0589* | |
H2A | 0.09426 | 1.07055 | −0.35075 | 0.0690* | |
H2B | 0.02682 | 0.92626 | −0.36587 | 0.0690* | |
H4A | 0.27354 | 1.19502 | 0.10514 | 0.0831* | |
H4B | 0.26913 | 1.09607 | 0.24285 | 0.0831* | |
H6 | 0.04414 | 0.69920 | 0.08567 | 0.0578* | |
H7A | 0.10386 | 0.75354 | 0.33305 | 0.0682* | |
H7B | 0.13408 | 0.90891 | 0.36339 | 0.0682* | |
H9 | 0.26158 | 0.90228 | 0.57429 | 0.0542* | |
H13 | 0.32619 | 0.76023 | 0.19099 | 0.0540* | |
H14A | 0.36428 | 1.00926 | 0.76587 | 0.0955* | |
H14B | 0.41563 | 0.94859 | 0.91885 | 0.0955* | |
H14C | 0.30728 | 0.85986 | 0.83196 | 0.0955* | |
H15A | 0.53305 | 0.62400 | 0.72187 | 0.1328* | |
H15B | 0.66225 | 0.64316 | 0.68745 | 0.1328* | |
H15C | 0.56371 | 0.58310 | 0.56618 | 0.1328* | |
H16A | 0.43188 | 0.61417 | 0.12954 | 0.1077* | |
H16B | 0.56356 | 0.65035 | 0.10126 | 0.1077* | |
H16C | 0.49499 | 0.76465 | 0.07415 | 0.1077* | |
H7 | 0.13895 | 0.47592 | 1.09892 | 0.1155* | |
H18A | 0.17318 | 0.59359 | 0.75535 | 0.0719* | |
H18B | 0.29921 | 0.57640 | 0.75171 | 0.0719* | |
H19A | 0.10431 | 0.35621 | 0.71116 | 0.0717* | |
H19B | 0.23141 | 0.35296 | 0.68798 | 0.0717* | |
H20A | 0.11585 | 0.52405 | 0.49846 | 0.0695* | |
H20B | 0.23641 | 0.50118 | 0.47063 | 0.0695* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0623 (9) | 0.0730 (9) | 0.0425 (7) | 0.0242 (7) | −0.0178 (6) | −0.0137 (6) |
O2 | 0.0463 (8) | 0.0617 (8) | 0.0632 (9) | 0.0194 (6) | −0.0184 (6) | −0.0057 (7) |
O3 | 0.0579 (8) | 0.0791 (10) | 0.0521 (8) | 0.0335 (7) | −0.0016 (7) | −0.0095 (7) |
N1 | 0.0559 (10) | 0.0568 (9) | 0.0362 (8) | 0.0191 (8) | −0.0087 (7) | −0.0075 (7) |
N2 | 0.0778 (12) | 0.0601 (10) | 0.0335 (8) | 0.0206 (9) | −0.0137 (8) | −0.0041 (7) |
N3 | 0.0618 (10) | 0.0559 (9) | 0.0368 (8) | 0.0224 (8) | −0.0123 (7) | −0.0060 (7) |
N4 | 0.0913 (14) | 0.0665 (11) | 0.0453 (9) | 0.0185 (10) | −0.0269 (9) | −0.0106 (8) |
C2 | 0.0529 (10) | 0.0565 (11) | 0.0346 (9) | 0.0259 (9) | −0.0067 (7) | −0.0062 (8) |
C4 | 0.0531 (10) | 0.0624 (11) | 0.0363 (9) | 0.0256 (9) | −0.0111 (8) | −0.0091 (8) |
C5 | 0.0447 (10) | 0.0671 (12) | 0.0344 (9) | 0.0264 (9) | −0.0048 (7) | −0.0015 (8) |
C6 | 0.0487 (10) | 0.0601 (11) | 0.0380 (9) | 0.0215 (9) | −0.0031 (8) | 0.0009 (8) |
C7 | 0.0475 (11) | 0.0916 (16) | 0.0351 (10) | 0.0294 (10) | −0.0042 (8) | 0.0037 (9) |
C8 | 0.0441 (9) | 0.0540 (10) | 0.0318 (8) | 0.0150 (8) | −0.0049 (7) | 0.0054 (7) |
C9 | 0.0473 (10) | 0.0534 (10) | 0.0363 (9) | 0.0182 (8) | −0.0022 (7) | 0.0003 (7) |
C10 | 0.0480 (10) | 0.0441 (9) | 0.0370 (9) | 0.0099 (8) | −0.0096 (7) | −0.0002 (7) |
C11 | 0.0411 (9) | 0.0447 (9) | 0.0460 (10) | 0.0120 (8) | −0.0097 (8) | 0.0014 (8) |
C12 | 0.0455 (10) | 0.0442 (9) | 0.0441 (10) | 0.0145 (8) | 0.0001 (8) | 0.0013 (7) |
C13 | 0.0473 (10) | 0.0536 (10) | 0.0337 (9) | 0.0154 (8) | −0.0054 (7) | −0.0002 (7) |
C14 | 0.0773 (15) | 0.0705 (14) | 0.0450 (11) | 0.0219 (12) | −0.0100 (10) | −0.0156 (10) |
C15 | 0.0932 (19) | 0.0690 (16) | 0.105 (2) | 0.0394 (14) | −0.0495 (17) | −0.0099 (14) |
C16 | 0.0840 (17) | 0.0896 (17) | 0.0559 (13) | 0.0452 (14) | 0.0034 (12) | −0.0126 (12) |
O4 | 0.0981 (13) | 0.0656 (10) | 0.0387 (7) | −0.0026 (9) | −0.0159 (8) | −0.0004 (7) |
O5 | 0.0904 (12) | 0.0756 (10) | 0.0283 (7) | 0.0067 (8) | −0.0054 (7) | −0.0004 (6) |
O6 | 0.0981 (13) | 0.1065 (14) | 0.0543 (9) | 0.0601 (12) | −0.0022 (9) | −0.0001 (9) |
O7 | 0.1041 (13) | 0.0958 (13) | 0.0474 (9) | 0.0590 (11) | 0.0186 (9) | 0.0171 (8) |
C17 | 0.0562 (11) | 0.0426 (9) | 0.0386 (9) | 0.0085 (8) | −0.0055 (8) | −0.0076 (7) |
C18 | 0.0796 (15) | 0.0553 (12) | 0.0394 (10) | 0.0083 (10) | 0.0014 (10) | −0.0017 (8) |
C19 | 0.0742 (14) | 0.0598 (12) | 0.0357 (10) | 0.0023 (10) | −0.0059 (9) | −0.0030 (8) |
C20 | 0.0698 (14) | 0.0612 (12) | 0.0377 (10) | 0.0083 (10) | −0.0001 (9) | −0.0026 (9) |
C21 | 0.0522 (11) | 0.0654 (12) | 0.0319 (9) | 0.0075 (9) | 0.0003 (8) | −0.0012 (8) |
Geometric parameters (Å, º) top
O1—C10 | 1.364 (2) | C9—C10 | 1.396 (3) |
O1—C14 | 1.411 (3) | C10—C11 | 1.380 (3) |
O2—C11 | 1.385 (2) | C11—C12 | 1.392 (3) |
O2—C15 | 1.421 (3) | C12—C13 | 1.395 (3) |
O3—C12 | 1.362 (3) | C6—H6 | 0.9301 |
O3—C16 | 1.417 (3) | C7—H7B | 0.9702 |
O4—C21 | 1.239 (3) | C7—H7A | 0.9701 |
O5—C21 | 1.272 (2) | C9—H9 | 0.9301 |
O6—C17 | 1.196 (3) | C13—H13 | 0.9305 |
O7—C17 | 1.296 (3) | C14—H14B | 0.9596 |
O7—H7 | 0.8203 | C14—H14A | 0.9605 |
N1—C6 | 1.368 (2) | C14—H14C | 0.9604 |
N1—C2 | 1.359 (3) | C15—H15B | 0.9603 |
N2—C2 | 1.338 (2) | C15—H15C | 0.9595 |
N3—C2 | 1.321 (3) | C15—H15A | 0.9599 |
N3—C4 | 1.350 (2) | C16—H16B | 0.9600 |
N4—C4 | 1.317 (3) | C16—H16A | 0.9597 |
N1—H1 | 0.8600 | C16—H16C | 0.9599 |
N2—H2B | 0.8601 | C17—C18 | 1.507 (3) |
N2—H2A | 0.8599 | C18—C19 | 1.505 (3) |
N4—H4B | 0.8603 | C19—C20 | 1.516 (3) |
N4—H4A | 0.8599 | C20—C21 | 1.503 (3) |
C4—C5 | 1.446 (3) | C18—H18A | 0.9698 |
C5—C7 | 1.507 (3) | C18—H18B | 0.9700 |
C5—C6 | 1.339 (3) | C19—H19A | 0.9704 |
C7—C8 | 1.526 (3) | C19—H19B | 0.9702 |
C8—C9 | 1.381 (3) | C20—H20A | 0.9696 |
C8—C13 | 1.374 (3) | C20—H20B | 0.9702 |
| | | |
O1···O2 | 2.666 (2) | C16···H13 | 2.5322 |
O1···C15 | 3.334 (4) | C17···H16Avi | 3.0116 |
O2···O1 | 2.666 (2) | C21···H15Bv | 2.9706 |
O2···O3 | 2.667 (2) | C21···H7iv | 2.9517 |
O2···N4i | 3.053 (3) | C21···H1iii | 2.6567 |
O3···O2 | 2.667 (2) | C21···H2Biii | 2.8084 |
O3···C15 | 3.173 (4) | H1···O4iii | 2.8259 |
O4···N2ii | 2.890 (3) | H1···O5iii | 1.8633 |
O4···N2iii | 2.798 (3) | H1···C21iii | 2.6567 |
O5···N1iii | 2.720 (3) | H1···H2B | 2.2849 |
O5···C17iv | 3.396 (3) | H2A···O4ix | 2.1266 |
O5···O7iv | 2.616 (3) | H2B···H1 | 2.2849 |
O6···C16v | 3.355 (4) | H2B···O4iii | 1.9420 |
O6···N4ii | 3.037 (3) | H2B···C21iii | 2.8084 |
O7···O5vi | 2.616 (3) | H4A···H15Bi | 2.5098 |
O7···C6vi | 3.109 (3) | H4A···C15i | 2.9911 |
O2···H4Bi | 2.3962 | H4A···O6ix | 2.2081 |
O3···H15C | 2.7056 | H4B···C7 | 2.6171 |
O3···H14Ai | 2.7620 | H4B···C8 | 2.8094 |
O4···H19B | 2.7421 | H4B···H7B | 2.3848 |
O4···H19A | 2.5879 | H4B···O2i | 2.3962 |
O4···H2Biii | 1.9420 | H4B···C15i | 2.9418 |
O4···H1iii | 2.8259 | H6···H7A | 2.3077 |
O4···H2Aii | 2.1266 | H6···O7viii | 2.8803 |
O5···H7iv | 1.8175 | H6···O7iv | 2.5931 |
O5···H1iii | 1.8633 | H6···H19Aviii | 2.5579 |
O6···H16Avi | 2.6883 | H7···C21vi | 2.9517 |
O6···H15Bvii | 2.7757 | H7···O5vi | 1.8175 |
O6···H19B | 2.8673 | H7A···H19Aviii | 2.4814 |
O6···H4Aii | 2.2081 | H7A···H6 | 2.3077 |
O6···H16Bv | 2.4007 | H7B···N2x | 2.8652 |
O7···H6viii | 2.8803 | H7B···N4 | 2.8347 |
O7···H6vi | 2.5931 | H7B···H4B | 2.3848 |
N1···O5iii | 2.720 (3) | H7B···H9 | 2.3111 |
N2···O4iii | 2.798 (3) | H9···H14A | 2.2045 |
N2···O4ix | 2.890 (3) | H9···C14 | 2.4773 |
N3···C14iv | 3.430 (3) | H9···H7B | 2.3111 |
N4···O6ix | 3.037 (3) | H9···H14C | 2.3126 |
N4···C8 | 3.363 (3) | H13···C5 | 2.7743 |
N4···O2i | 3.053 (3) | H13···C16 | 2.5322 |
N4···C15i | 3.301 (4) | H13···H16A | 2.3006 |
N2···H7Bx | 2.8652 | H13···H16C | 2.3403 |
N4···H7B | 2.8347 | H14A···C9 | 2.6555 |
N4···H15Bi | 2.8911 | H14A···H9 | 2.2045 |
C2···C14iv | 3.530 (4) | H14A···O3i | 2.7620 |
C2···C4x | 3.587 (3) | H14A···C12i | 2.9430 |
C4···C2x | 3.587 (3) | H14B···H16Cvi | 2.5298 |
C6···O7iv | 3.109 (3) | H14B···H14Bxi | 2.4419 |
C8···N4 | 3.363 (3) | H14C···C2vi | 2.9734 |
C10···C11i | 3.531 (3) | H14C···C9 | 2.7383 |
C10···C10i | 3.554 (3) | H14C···H9 | 2.3126 |
C11···C10i | 3.531 (3) | H15A···C10 | 3.0577 |
C12···C14i | 3.561 (4) | H15B···O6vii | 2.7757 |
C14···C12i | 3.561 (4) | H15B···N4i | 2.8911 |
C14···C2vi | 3.530 (4) | H15B···C21v | 2.9706 |
C14···N3vi | 3.430 (3) | H15B···H4Ai | 2.5098 |
C15···O3 | 3.173 (4) | H15C···O3 | 2.7056 |
C15···O1 | 3.334 (4) | H15C···C12 | 2.9323 |
C15···N4i | 3.301 (4) | H15C···H15Cv | 2.3012 |
C16···O6v | 3.355 (4) | H16A···O6iv | 2.6883 |
C17···O5vi | 3.396 (3) | H16A···C13 | 2.7377 |
C2···H14Civ | 2.9734 | H16A···C17iv | 3.0116 |
C5···H13 | 2.7743 | H16A···H13 | 2.3006 |
C7···H4B | 2.6171 | H16B···O6v | 2.4007 |
C8···H4B | 2.8094 | H16C···C13 | 2.7578 |
C9···H14A | 2.6555 | H16C···C14iv | 3.0914 |
C9···H14C | 2.7383 | H16C···H13 | 2.3403 |
C10···H18B | 3.0182 | H16C···H14Biv | 2.5298 |
C10···H15A | 3.0577 | H18A···H20A | 2.4250 |
C12···H15C | 2.9323 | H18B···C10 | 3.0182 |
C12···H14Ai | 2.9430 | H19A···O4 | 2.5879 |
C13···H16C | 2.7578 | H19A···H6viii | 2.5579 |
C13···H16A | 2.7377 | H19A···H7Aviii | 2.4814 |
C14···H16Cvi | 3.0914 | H19B···O4 | 2.7421 |
C14···H9 | 2.4773 | H19B···O6 | 2.8673 |
C15···H4Ai | 2.9911 | H20A···H18A | 2.4250 |
C15···H4Bi | 2.9418 | | |
| | | |
C10—O1—C14 | 116.40 (16) | C10—C9—H9 | 120.02 |
C11—O2—C15 | 113.33 (19) | C8—C9—H9 | 120.05 |
C12—O3—C16 | 117.51 (17) | C12—C13—H13 | 120.08 |
C17—O7—H7 | 109.42 | C8—C13—H13 | 120.09 |
C2—N1—C6 | 120.61 (16) | O1—C14—H14A | 109.48 |
C2—N3—C4 | 117.39 (17) | O1—C14—H14B | 109.53 |
C2—N1—H1 | 119.68 | H14A—C14—H14B | 109.47 |
C6—N1—H1 | 119.71 | H14A—C14—H14C | 109.40 |
C2—N2—H2A | 120.02 | O1—C14—H14C | 109.48 |
H2A—N2—H2B | 120.00 | H14B—C14—H14C | 109.47 |
C2—N2—H2B | 119.97 | O2—C15—H15B | 109.43 |
H4A—N4—H4B | 119.99 | O2—C15—H15C | 109.49 |
C4—N4—H4B | 119.98 | O2—C15—H15A | 109.46 |
C4—N4—H4A | 120.03 | H15A—C15—H15C | 109.53 |
N2—C2—N3 | 119.60 (18) | H15B—C15—H15C | 109.48 |
N1—C2—N3 | 122.10 (16) | H15A—C15—H15B | 109.45 |
N1—C2—N2 | 118.30 (17) | O3—C16—H16B | 109.43 |
N3—C4—C5 | 123.49 (17) | O3—C16—H16C | 109.44 |
N3—C4—N4 | 115.62 (18) | H16A—C16—H16B | 109.51 |
N4—C4—C5 | 120.87 (17) | H16A—C16—H16C | 109.51 |
C4—C5—C6 | 114.99 (16) | H16B—C16—H16C | 109.49 |
C6—C5—C7 | 121.26 (19) | O3—C16—H16A | 109.45 |
C4—C5—C7 | 123.50 (18) | O6—C17—O7 | 121.99 (18) |
N1—C6—C5 | 121.36 (18) | O6—C17—C18 | 125.14 (19) |
C5—C7—C8 | 117.48 (17) | O7—C17—C18 | 112.85 (18) |
C7—C8—C13 | 122.08 (16) | C17—C18—C19 | 110.45 (15) |
C9—C8—C13 | 120.37 (17) | C18—C19—C20 | 113.27 (16) |
C7—C8—C9 | 117.35 (17) | C19—C20—C21 | 114.01 (16) |
C8—C9—C10 | 119.93 (17) | O4—C21—C20 | 119.42 (16) |
O1—C10—C11 | 115.66 (17) | O5—C21—C20 | 116.42 (17) |
C9—C10—C11 | 120.26 (16) | O4—C21—O5 | 124.11 (18) |
O1—C10—C9 | 124.08 (17) | C17—C18—H18A | 109.55 |
C10—C11—C12 | 119.34 (17) | C17—C18—H18B | 109.54 |
O2—C11—C10 | 120.07 (16) | C19—C18—H18A | 109.58 |
O2—C11—C12 | 120.57 (17) | C19—C18—H18B | 109.57 |
O3—C12—C11 | 114.75 (17) | H18A—C18—H18B | 108.12 |
O3—C12—C13 | 125.00 (16) | C18—C19—H19A | 108.93 |
C11—C12—C13 | 120.26 (17) | C18—C19—H19B | 108.94 |
C8—C13—C12 | 119.83 (16) | C20—C19—H19A | 108.91 |
C5—C6—H6 | 119.36 | C20—C19—H19B | 108.94 |
N1—C6—H6 | 119.28 | H19A—C19—H19B | 107.70 |
C5—C7—H7A | 107.96 | C19—C20—H20A | 108.74 |
C5—C7—H7B | 107.95 | C19—C20—H20B | 108.71 |
C8—C7—H7B | 107.92 | C21—C20—H20A | 108.79 |
H7A—C7—H7B | 107.19 | C21—C20—H20B | 108.75 |
C8—C7—H7A | 107.91 | H20A—C20—H20B | 107.66 |
| | | |
C14—O1—C10—C9 | −0.8 (3) | C7—C8—C13—C12 | −174.13 (19) |
C14—O1—C10—C11 | −179.96 (18) | C7—C8—C9—C10 | 173.84 (19) |
C15—O2—C11—C10 | 96.3 (2) | C9—C8—C13—C12 | 0.6 (3) |
C15—O2—C11—C12 | −85.6 (2) | C13—C8—C9—C10 | −1.1 (3) |
C16—O3—C12—C11 | −178.61 (19) | C8—C9—C10—C11 | 0.9 (3) |
C16—O3—C12—C13 | 1.5 (3) | C8—C9—C10—O1 | −178.28 (17) |
C6—N1—C2—N2 | −179.43 (19) | C9—C10—C11—O2 | 178.08 (16) |
C6—N1—C2—N3 | 1.0 (3) | O1—C10—C11—C12 | 179.14 (16) |
C2—N1—C6—C5 | −1.8 (3) | O1—C10—C11—O2 | −2.7 (2) |
C4—N3—C2—N1 | 1.3 (3) | C9—C10—C11—C12 | −0.1 (3) |
C2—N3—C4—C5 | −2.9 (3) | O2—C11—C12—O3 | 1.5 (3) |
C4—N3—C2—N2 | −178.3 (2) | C10—C11—C12—C13 | −0.5 (3) |
C2—N3—C4—N4 | 178.8 (2) | O2—C11—C12—C13 | −178.61 (17) |
N3—C4—C5—C7 | −172.1 (2) | C10—C11—C12—O3 | 179.63 (16) |
N4—C4—C5—C6 | −179.6 (2) | O3—C12—C13—C8 | −179.88 (18) |
N4—C4—C5—C7 | 6.1 (3) | C11—C12—C13—C8 | 0.2 (3) |
N3—C4—C5—C6 | 2.2 (3) | O7—C17—C18—C19 | −113.2 (2) |
C7—C5—C6—N1 | 174.68 (19) | O6—C17—C18—C19 | 65.4 (3) |
C4—C5—C7—C8 | −72.8 (3) | C17—C18—C19—C20 | 172.29 (19) |
C6—C5—C7—C8 | 113.2 (2) | C18—C19—C20—C21 | −172.7 (2) |
C4—C5—C6—N1 | 0.2 (3) | C19—C20—C21—O5 | 175.3 (2) |
C5—C7—C8—C13 | −36.7 (3) | C19—C20—C21—O4 | −2.1 (3) |
C5—C7—C8—C9 | 148.4 (2) | | |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y−1, z+1; (iii) −x, −y+1, −z; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) x, y, z+1; (vii) −x+1, −y+1, −z+2; (viii) −x, −y+1, −z+1; (ix) x, y+1, z−1; (x) −x, −y+2, −z; (xi) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5iii | 0.8600 | 1.8633 | 2.720 (3) | 174.16 |
N2—H2A···O4ix | 0.8599 | 2.1266 | 2.890 (3) | 147.64 |
N2—H2B···O4iii | 0.8601 | 1.9420 | 2.798 (3) | 173.23 |
N4—H4A···O6ix | 0.8599 | 2.2081 | 3.037 (3) | 161.81 |
N4—H4B···O2i | 0.8603 | 2.3962 | 3.053 (3) | 133.56 |
O7—H7···O5vi | 0.8203 | 1.8175 | 2.616 (3) | 164.12 |
C6—H6···O7iv | 0.9301 | 2.5931 | 3.109 (3) | 115.46 |
C16—H16B···O6v | 0.9600 | 2.4007 | 3.355 (4) | 172.79 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (iii) −x, −y+1, −z; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) x, y, z+1; (ix) x, y+1, z−1. |