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In the title compound, trimethoprim salicyl­ate methanol solvate [3,4,5-tri­methoxy­benzyl)­pyrimidin-1-ium salicyl­ate methanol solvate], C14H19N4O3+·C7H5O3·CH4O, the trimethoprim mol­ecule is protonated at N1. The carboxyl­ate group of the salicyl­ate ion interacts with the protonated pyrimidine moiety of trimethoprim through a pair of nearly parallel N—H...O hydrogen bonds. This is reminiscent of the carboxyl­ate–trimethoprim interaction observed in di­hydro­folate reductase–trimethoprim complexes. The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N—H...N hydrogen bonds involving the 4-amino group and the unsubstituted pyrimidine N atom. The pyrimidine plane makes a dihedral angle of 89.5 (4)° with the phenyl ring in the trimethoprim cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000909/wn6077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000909/wn6077Isup2.hkl
Contains datablock I

CCDC reference: 180801

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • H-atom completeness 86%
  • R factor = 0.063
  • wR factor = 0.216
  • Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_353 Alert B Long N-H Bond (0.87A) N(2) - H(2B) = 1.09 Ang.
Yellow Alert Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.621 Test value = 0.600 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT_321 Alert C Check Hybridisation of C(1A) in solvent/ion ? PLAT_353 Alert C Long N-H Bond (0.87A) N(1) - H(1) = 1.04 Ang. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22 H28 N4 O7 Atom count from the _atom_site data: C22 H24 N4 O7 CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C22 H28 N4 O7 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 44.00 44.00 0.00 H 56.00 48.00 8.00 N 8.00 8.00 0.00 O 14.00 14.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
4 Alert Level C = Please check

Computing details top

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

(I) top
Crystal data top
C14H19N4O3+·C7H5O3·CH4OZ = 2
Mr = 460.48F(000) = 488
Triclinic, P1Dx = 1.383 Mg m3
a = 10.0139 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2600 (19) ÅCell parameters from 25 reflections
c = 11.984 (9) Åθ = 10–15°
α = 105.93 (3)°µ = 0.10 mm1
β = 109.17 (5)°T = 293 K
γ = 92.50 (2)°Needle, colourless
V = 1106.1 (10) Å30.3 × 0.3 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.97, Tmax = 0.99l = 1314
4377 measured reflections2 standard reflections every 60 min
3889 independent reflections intensity decay: none
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H atoms treated by a mixture of independent and constrained refinement
S = 1.65 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
3889 reflections(Δ/σ)max < 0.001
365 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
O10.4218 (2)0.6256 (3)0.5894 (2)0.0823 (9)
O20.4464 (2)0.4437 (3)0.7128 (2)0.0854 (9)
O30.2303 (3)0.2147 (3)0.6258 (2)0.0917 (11)
N10.3240 (2)0.0649 (2)0.15946 (19)0.0437 (7)
N20.3404 (3)0.1479 (3)0.0256 (2)0.0554 (8)
N30.1505 (2)0.0151 (2)0.06668 (18)0.0419 (6)
N40.0411 (2)0.1747 (2)0.1141 (2)0.0491 (7)
C20.2701 (3)0.0213 (3)0.0832 (2)0.0412 (7)
C40.0788 (2)0.1423 (2)0.1319 (2)0.0378 (7)
C50.1277 (2)0.2390 (2)0.2156 (2)0.0398 (7)
C60.2533 (3)0.1938 (3)0.2231 (2)0.0419 (7)
C70.0483 (3)0.3805 (3)0.2867 (2)0.0438 (8)
C80.0865 (2)0.3906 (2)0.3947 (2)0.0385 (7)
C90.1938 (3)0.5017 (3)0.4352 (3)0.0457 (8)
C100.3136 (3)0.5178 (3)0.5397 (3)0.0538 (9)
C110.3263 (3)0.4244 (3)0.6069 (3)0.0564 (9)
C120.2229 (3)0.3113 (3)0.5624 (2)0.0542 (9)
C130.1023 (3)0.2964 (3)0.4589 (2)0.0469 (8)
C140.4159 (6)0.7222 (5)0.5235 (5)0.101 (2)
C150.4187 (4)0.4731 (4)0.8263 (3)0.0823 (13)
C160.3194 (7)0.1231 (5)0.6157 (5)0.129 (3)
O40.4364 (2)1.0021 (2)0.2017 (2)0.0633 (7)
O50.4079 (2)0.7936 (2)0.07043 (18)0.0588 (7)
O60.2159 (3)0.6108 (2)0.0426 (2)0.0743 (8)
C1'0.2460 (3)0.8390 (3)0.1789 (2)0.0475 (8)
C2'0.1747 (3)0.7053 (3)0.1228 (3)0.0523 (9)
C3'0.0546 (3)0.6663 (4)0.1490 (3)0.0668 (11)
C4'0.0094 (4)0.7599 (4)0.2305 (4)0.0757 (15)
C5'0.0815 (5)0.8911 (5)0.2853 (5)0.0857 (17)
C6'0.1987 (3)0.9316 (3)0.2603 (3)0.0656 (11)
C7'0.3731 (3)0.8833 (3)0.1496 (2)0.0488 (8)
O70.2737 (3)0.3882 (3)0.1610 (3)0.0950 (11)
C1A0.3360 (10)0.2692 (11)0.2206 (9)0.207 (5)
H10.423 (6)0.052 (5)0.168 (5)0.15 (2)*
H2A0.319 (4)0.208 (4)0.022 (4)0.081 (12)*
H2B0.439 (4)0.180 (3)0.037 (3)0.078 (10)*
H4A0.068930.115710.063130.0589*
H4B0.090800.254510.153450.0589*
H60.303 (3)0.242 (3)0.268 (2)0.046 (7)*
H7A0.031 (3)0.416 (3)0.231 (3)0.044 (7)*
H7B0.102 (4)0.437 (3)0.318 (3)0.068 (9)*
H90.189 (4)0.555 (3)0.388 (3)0.070 (10)*
H130.035 (3)0.220 (3)0.437 (2)0.046 (7)*
H14A0.418 (5)0.689 (4)0.441 (5)0.109 (15)*
H14B0.339 (4)0.779 (4)0.514 (3)0.078 (12)*
H14C0.488 (6)0.806 (5)0.559 (5)0.129 (16)*
H15A0.363910.394160.826630.1236*
H15B0.507590.495960.895100.1236*
H15C0.365860.549000.833230.1236*
H16A0.416240.168630.656220.1933*
H16B0.303620.056050.654050.1933*
H16C0.302400.078710.529580.1933*
H3'0.022 (4)0.565 (4)0.108 (3)0.084 (11)*
H4'0.084 (4)0.750 (3)0.250 (3)0.085 (11)*
H5'0.058 (5)0.940 (5)0.330 (5)0.106 (16)*
H6'0.249 (4)1.021 (3)0.295 (3)0.065 (9)*
H6A0.300 (5)0.666 (4)0.032 (4)0.094 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0527 (12)0.0803 (16)0.0876 (16)0.0240 (11)0.0289 (12)0.0150 (13)
O20.0471 (12)0.123 (2)0.0583 (13)0.0211 (12)0.0046 (10)0.0004 (13)
O30.122 (2)0.105 (2)0.0787 (16)0.0501 (17)0.0468 (15)0.0568 (15)
N10.0361 (11)0.0499 (12)0.0473 (11)0.0020 (9)0.0194 (9)0.0131 (9)
N20.0486 (13)0.0488 (14)0.0656 (15)0.0060 (10)0.0297 (12)0.0030 (12)
N30.0348 (10)0.0436 (11)0.0450 (11)0.0021 (8)0.0187 (8)0.0057 (9)
N40.0394 (11)0.0469 (12)0.0564 (13)0.0081 (9)0.0245 (10)0.0019 (10)
C20.0343 (12)0.0471 (14)0.0422 (12)0.0005 (10)0.0151 (10)0.0127 (10)
C40.0306 (11)0.0455 (13)0.0385 (12)0.0011 (10)0.0114 (9)0.0162 (10)
C50.0350 (12)0.0439 (13)0.0393 (12)0.0022 (10)0.0134 (10)0.0113 (10)
C60.0392 (12)0.0474 (14)0.0419 (12)0.0076 (11)0.0198 (11)0.0110 (10)
C70.0430 (13)0.0444 (14)0.0448 (14)0.0064 (11)0.0175 (11)0.0125 (11)
C80.0387 (12)0.0357 (12)0.0416 (12)0.0023 (9)0.0187 (10)0.0078 (10)
C90.0453 (14)0.0398 (13)0.0532 (15)0.0015 (11)0.0255 (12)0.0068 (12)
C100.0355 (13)0.0552 (16)0.0585 (16)0.0053 (11)0.0237 (12)0.0084 (13)
C110.0386 (14)0.0768 (19)0.0449 (14)0.0164 (13)0.0130 (12)0.0058 (14)
C120.0587 (17)0.0589 (17)0.0466 (15)0.0186 (14)0.0197 (13)0.0160 (13)
C130.0546 (15)0.0372 (13)0.0454 (14)0.0012 (12)0.0171 (12)0.0089 (10)
C140.106 (4)0.072 (3)0.113 (4)0.034 (3)0.063 (3)0.011 (3)
C150.084 (2)0.104 (3)0.0426 (16)0.023 (2)0.0104 (16)0.0102 (17)
C160.204 (6)0.102 (3)0.132 (4)0.076 (4)0.087 (4)0.074 (3)
O40.0501 (11)0.0606 (12)0.0802 (14)0.0110 (9)0.0311 (10)0.0161 (10)
O50.0486 (11)0.0674 (12)0.0612 (12)0.0053 (9)0.0272 (9)0.0137 (10)
O60.0708 (14)0.0628 (13)0.0874 (16)0.0140 (11)0.0408 (12)0.0080 (11)
C1'0.0363 (12)0.0592 (16)0.0521 (14)0.0018 (11)0.0147 (11)0.0269 (12)
C2'0.0418 (14)0.0630 (17)0.0558 (16)0.0009 (12)0.0194 (12)0.0228 (13)
C3'0.0518 (17)0.075 (2)0.080 (2)0.0094 (15)0.0242 (15)0.0353 (18)
C4'0.0564 (18)0.091 (3)0.105 (3)0.0080 (18)0.0490 (19)0.045 (2)
C5'0.082 (3)0.089 (3)0.110 (3)0.018 (2)0.065 (3)0.029 (2)
C6'0.0555 (17)0.0611 (19)0.090 (2)0.0021 (15)0.0377 (17)0.0250 (17)
C7'0.0325 (12)0.0626 (16)0.0530 (15)0.0064 (11)0.0136 (11)0.0241 (13)
O70.0862 (18)0.0902 (18)0.106 (2)0.0091 (14)0.0464 (16)0.0141 (15)
C1A0.170 (8)0.241 (10)0.191 (8)0.008 (7)0.054 (6)0.050 (7)
Geometric parameters (Å, º) top
O1—C101.365 (4)C10—C111.396 (5)
O1—C141.419 (6)C11—C121.377 (5)
O2—C111.391 (4)C12—C131.384 (4)
O2—C151.431 (4)C6—H60.91 (3)
O3—C121.396 (4)C7—H7B0.90 (4)
O3—C161.333 (7)C7—H7A0.90 (3)
O4—C7'1.238 (4)C9—H90.88 (3)
O5—C7'1.278 (4)C13—H130.93 (3)
O6—C2'1.348 (4)C14—H14A0.96 (5)
O6—H6A1.06 (5)C14—H14C0.99 (6)
O7—C1A1.626 (12)C14—H14B0.98 (4)
N1—C61.357 (4)C15—H15C0.9605
N1—C21.353 (4)C15—H15B0.9596
N2—C21.330 (4)C15—H15A0.9599
N3—C21.331 (4)C16—H16B0.9598
N3—C41.349 (3)C16—H16A0.9598
N4—C41.330 (3)C16—H16C0.9599
N1—H11.04 (6)C1'—C6'1.383 (4)
N2—H2B1.09 (4)C1'—C2'1.392 (5)
N2—H2A0.81 (4)C1'—C7'1.510 (4)
N4—H4A0.8606C2'—C3'1.407 (5)
N4—H4B0.8596C3'—C4'1.376 (6)
C4—C51.431 (3)C4'—C5'1.372 (7)
C5—C71.497 (4)C5'—C6'1.377 (6)
C5—C61.361 (4)C3'—H3'1.01 (4)
C7—C81.508 (4)C4'—H4'1.04 (4)
C8—C91.392 (4)C5'—H5'0.73 (5)
C8—C131.376 (4)C6'—H6'0.94 (3)
C9—C101.385 (5)
O1···O22.655 (5)C6···H15Cii3.0704
O1···C1Ai2.651 (11)C6'···H16Civ2.9596
O2···C163.218 (7)C7···H4B2.5780
O2···O12.655 (5)C7'···H6A2.22 (4)
O2···O32.832 (5)C7'···H16Ai2.7756
O2···C1Ai3.327 (12)C7'···H1v2.53 (6)
O2···O7i2.912 (5)C7'···H2Bv2.66 (4)
O3···C4'ii3.364 (6)C8···H4B2.8603
O3···C153.074 (5)C9···H14B2.89 (4)
O3···O22.832 (5)C9···H14A2.86 (5)
O4···C16i3.274 (7)C10···H6ii2.91 (3)
O4···C2iii3.337 (4)C11···H7Bii2.96 (4)
O4···C1Aiv2.936 (12)C11···H16A2.9589
O4···N1v2.696 (4)C11···H14Ai3.02 (5)
O5···C6iii3.388 (4)C12···H15A2.8679
O5···N2v2.817 (4)C12···H7Bii3.09 (4)
O5···O62.499 (4)C14···H92.54 (4)
O6···O52.499 (4)C14···H6ii3.01 (3)
O6···O72.987 (5)C15···H15Bxi3.0939
O7···C15i3.275 (6)H1···H2B2.43 (6)
O7···N42.926 (4)H1···C7'viii2.53 (6)
O7···N2vi3.102 (5)H1···O4viii1.68 (6)
O7···O2i2.912 (5)H1···O5viii2.81 (6)
O7···O62.987 (5)H2A···O7vi2.30 (4)
O1···H6ii2.53 (3)H2A···C1Avi2.23 (4)
O2···H16A2.6938H2B···C7'viii2.66 (4)
O2···H14Ai2.74 (5)H2B···O5viii1.74 (4)
O3···H15A2.4921H2B···H12.43 (6)
O3···H4'ii2.38 (4)H3'···H7A2.54 (5)
O4···H6'2.47 (4)H3'···H3'iii2.45 (5)
O4···H16Ai2.8910H3'···O6iii2.68 (4)
O4···H1v1.68 (6)H4'···O3ii2.38 (4)
O4···H16Bi2.8050H4A···C4vi3.0427
O4···H14Cvii2.83 (5)H4A···N3vi2.1616
O5···H6A1.52 (5)H4A···H4Avi2.4906
O5···H2Bv1.74 (4)H4A···C1A2.8072
O5···H1v2.81 (6)H4B···O72.2018
O6···H3'iii2.68 (4)H4B···C1A2.3028
O7···H2Avi2.30 (4)H4B···C82.8603
O7···H15Bi2.8000H4B···C72.5780
O7···H4B2.2018H4B···H7A2.2742
N1···O4viii2.696 (4)H6···C10ii2.91 (3)
N1···C7'viii3.440 (5)H6···C14ii3.01 (3)
N2···O7vi3.102 (5)H6···O1ii2.53 (3)
N2···O5viii2.817 (4)H6···H7B2.57 (5)
N2···C1Avi2.886 (10)H6'···H16Civ2.5712
N3···N4vi3.019 (4)H6'···C1Aiv3.10 (4)
N3···C7'iii3.266 (4)H6'···O42.47 (4)
N4···O72.926 (4)H6A···C7'2.22 (4)
N4···N3vi3.019 (4)H6A···O51.52 (5)
N4···C83.353 (4)H7A···N42.74 (3)
N4···C1A2.808 (11)H7A···H3'2.54 (5)
N1···H16Bix2.7967H7A···H4B2.2742
N3···H4Avi2.1616H7A···H92.44 (5)
N4···H7A2.74 (3)H7B···C11ii2.96 (4)
C1A···O4x2.936 (12)H7B···C12ii3.09 (4)
C1A···N42.808 (11)H7B···H62.57 (5)
C1A···O1i2.651 (11)H9···H7A2.44 (5)
C1A···O2i3.327 (12)H9···H14A2.42 (7)
C1A···C14i3.227 (12)H9···C142.54 (4)
C1A···N2vi2.886 (10)H9···H14B2.47 (5)
C2···C7'iii3.355 (5)H13···C52.68 (2)
C2···O4iii3.337 (4)H14A···H92.42 (7)
C4···C133.581 (4)H14A···O2i2.74 (5)
C4'···O3ii3.364 (6)H14A···C92.86 (5)
C6···O5iii3.388 (4)H14A···C11i3.02 (5)
C7'···N1v3.440 (5)H14B···H92.47 (5)
C7'···N3iii3.266 (4)H14B···C92.89 (4)
C7'···C16i3.439 (7)H14C···C1Ai2.98 (6)
C7'···C2iii3.355 (5)H14C···O4vii2.83 (5)
C8···N43.353 (4)H15A···O32.4921
C13···C43.581 (4)H15A···C122.8679
C14···C1Ai3.227 (12)H15B···C15xi3.0939
C15···O7i3.275 (6)H15B···H15Bxi2.5474
C15···O33.074 (5)H15B···O7i2.8000
C16···O4i3.274 (7)H15C···C6ii3.0704
C16···C7'i3.439 (7)H16A···O4i2.8910
C16···O23.218 (7)H16A···C112.9589
C1A···H4B2.3028H16A···C7'i2.7756
C1A···H14Ci2.98 (6)H16A···O22.6938
C1A···H2Avi2.23 (4)H16B···N1ix2.7967
C1A···H6'x3.10 (4)H16B···O4i2.8050
C1A···H4A2.8072H16C···C6'x2.9596
C4···H4Avi3.0427H16C···H6'x2.5712
C5···H132.68 (2)H16C···C5'x3.0742
C5'···H16Civ3.0742
C10—O1—C14117.3 (3)C8—C7—H7A112 (2)
C11—O2—C15114.9 (3)C8—C9—H9119 (2)
C12—O3—C16118.6 (4)C10—C9—H9121 (2)
C2'—O6—H6A104 (2)C8—C13—H13123.5 (16)
C2—N1—C6119.1 (2)C12—C13—H13115.7 (17)
C2—N3—C4118.0 (2)O1—C14—H14B120 (2)
C2—N1—H1128 (3)O1—C14—H14C120 (3)
C6—N1—H1112 (3)H14A—C14—H14B103 (4)
H2A—N2—H2B112 (4)H14A—C14—H14C101 (4)
C2—N2—H2A126 (3)H14B—C14—H14C90 (4)
C2—N2—H2B121.5 (18)O1—C14—H14A117 (3)
C4—N4—H4A119.97O2—C15—H15B109.49
H4A—N4—H4B119.96O2—C15—H15C109.43
C4—N4—H4B120.06O2—C15—H15A109.48
N2—C2—N3120.1 (3)H15A—C15—H15C109.44
N1—C2—N2117.1 (3)H15B—C15—H15C109.47
N1—C2—N3122.8 (3)H15A—C15—H15B109.51
N3—C4—C5122.6 (2)O3—C16—H16A109.46
N4—C4—C5121.0 (2)O3—C16—H16C109.46
N3—C4—N4116.4 (2)H16A—C16—H16B109.50
C6—C5—C7122.7 (2)O3—C16—H16B109.41
C4—C5—C7122.3 (2)H16B—C16—H16C109.51
C4—C5—C6115.0 (2)H16A—C16—H16C109.50
N1—C6—C5122.4 (3)C2'—C1'—C7'120.2 (3)
C5—C7—C8115.8 (2)C6'—C1'—C7'120.2 (3)
C7—C8—C9119.5 (2)C2'—C1'—C6'119.7 (3)
C9—C8—C13119.0 (2)O6—C2'—C3'118.2 (3)
C7—C8—C13121.3 (2)C1'—C2'—C3'119.5 (3)
C8—C9—C10120.3 (3)O6—C2'—C1'122.2 (3)
O1—C10—C11114.9 (3)C2'—C3'—C4'119.9 (4)
C9—C10—C11120.3 (3)C3'—C4'—C5'119.7 (4)
O1—C10—C9124.7 (3)C4'—C5'—C6'121.3 (5)
O2—C11—C12121.7 (3)C1'—C6'—C5'119.9 (4)
O2—C11—C10119.4 (3)O4—C7'—C1'119.2 (3)
C10—C11—C12118.8 (3)O5—C7'—C1'116.7 (3)
O3—C12—C11121.2 (3)O4—C7'—O5124.0 (3)
C11—C12—C13120.6 (3)C2'—C3'—H3'109 (2)
O3—C12—C13118.0 (3)C4'—C3'—H3'130 (2)
C8—C13—C12120.8 (3)C3'—C4'—H4'128.4 (18)
N1—C6—H6110.1 (19)C5'—C4'—H4'111.4 (18)
C5—C6—H6127.5 (19)C4'—C5'—H5'119 (4)
C5—C7—H7A106 (2)C6'—C5'—H5'120 (4)
C5—C7—H7B113 (2)C1'—C6'—H6'117 (2)
C8—C7—H7B106 (2)C5'—C6'—H6'123 (2)
H7A—C7—H7B104 (3)
C14—O1—C10—C95.1 (5)C8—C9—C10—O1177.4 (3)
C14—O1—C10—C11178.7 (4)C8—C9—C10—C111.4 (5)
C15—O2—C11—C1269.2 (4)C9—C10—C11—C124.6 (5)
C15—O2—C11—C10114.4 (4)O1—C10—C11—O22.5 (4)
C16—O3—C12—C13107.2 (4)C9—C10—C11—O2178.9 (3)
C16—O3—C12—C1178.2 (4)O1—C10—C11—C12179.0 (3)
C6—N1—C2—N30.6 (4)C10—C11—C12—C135.5 (5)
C2—N1—C6—C51.7 (4)C10—C11—C12—O3180.0 (3)
C6—N1—C2—N2178.0 (2)O2—C11—C12—C13178.1 (3)
C2—N3—C4—C51.1 (3)O2—C11—C12—O33.6 (5)
C2—N3—C4—N4179.3 (2)C11—C12—C13—C83.3 (4)
C4—N3—C2—N11.9 (4)O3—C12—C13—C8177.9 (3)
C4—N3—C2—N2176.6 (2)C6'—C1'—C2'—C3'0.5 (5)
N4—C4—C5—C6178.6 (2)C6'—C1'—C2'—O6179.9 (3)
N4—C4—C5—C70.2 (3)C2'—C1'—C6'—C5'0.0 (5)
N3—C4—C5—C61.0 (3)C7'—C1'—C6'—C5'179.1 (3)
N3—C4—C5—C7179.4 (2)C2'—C1'—C7'—O4179.0 (3)
C6—C5—C7—C8107.1 (3)C2'—C1'—C7'—O51.4 (4)
C4—C5—C6—N12.4 (4)C6'—C1'—C7'—O41.9 (4)
C4—C5—C7—C874.6 (3)C6'—C1'—C7'—O5177.7 (3)
C7—C5—C6—N1179.3 (2)C7'—C1'—C2'—O60.8 (4)
C5—C7—C8—C9155.2 (2)C7'—C1'—C2'—C3'178.7 (3)
C5—C7—C8—C1328.7 (3)C1'—C2'—C3'—C4'0.6 (5)
C7—C8—C13—C12176.1 (3)O6—C2'—C3'—C4'179.9 (3)
C9—C8—C13—C120.0 (4)C2'—C3'—C4'—C5'0.3 (6)
C13—C8—C9—C100.9 (4)C3'—C4'—C5'—C6'0.1 (7)
C7—C8—C9—C10175.3 (3)C4'—C5'—C6'—C1'0.3 (7)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x, y+1, z; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) x, y, z; (vii) x+1, y+2, z+1; (viii) x1, y1, z; (ix) x, y, z+1; (x) x, y1, z; (xi) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4viii1.04 (6)1.68 (6)2.696 (4)165 (5)
N2—H2A···O7vi0.81 (4)2.30 (4)3.102 (5)176 (5)
N2—H2B···O5viii1.09 (4)1.74 (4)2.817 (4)171 (2)
N4—H4A···N3vi0.86062.16163.019 (4)174
N4—H4B···O70.85962.20182.926 (4)142
O6—H6A···O51.06 (5)1.52 (5)2.499 (4)151 (4)
C4—H4···O3ii1.04 (4)2.38 (4)3.364 (6)156 (3)
C6—H6···O1ii0.91 (3)2.53 (3)3.436 (4)175 (2)
C6—H6···O40.94 (3)2.47 (4)2.812 (4)102 (3)
C15—H15A···O30.95992.49213.074 (5)119
Symmetry codes: (ii) x, y+1, z+1; (vi) x, y, z; (viii) x1, y1, z.
 

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