The 1:2 adduct of benzene-1,2,4,5-tetracarboxylic acid and 4,4′-bipyridyl at 100 K has been studied by single-crystal neutron diffraction at 20, 200 and 296 K. The structure contains two short, strong N
O hydrogen bonds: one O—H
N hydrogen bond [O
N 2.6104 (17) Å at 20 K] and one short N—H
O hydrogen bond [N
O 2.5220 (17) Å at 20 K]. The N—H distance in the N—H
O hydrogen bond changes from 1.207 (3) Å at 20 K to 1.302 (4) Å at 296 K and the N
O distance increases to 2.5315 (16) Å at 296 K. At 200 K the H atom lies in an intermediate position 1.251 (6) Å from the N atom with an N
O separation of 2.520 (4) Å. The O—H
N hydrogen bond, on the other hand, does not change with temperature.
Supporting information
CCDC references: 144034; 227675; 227676; 227677
Data collection: MAD (Barthelemy, 1984) for hex20, hex296; LADI Control for hexladi; SMART (Bruker, 1998) for hex30x. Cell refinement: RAFD19 (Filhol, 1998) for hex20, hex296; LAUEGEN (Campbell) for hexladi; SAINT (Bruker, 1998) for hex30x. Data reduction: RETREAT (Wilkinson, et al. 1988) for hex20, hex296; INTEGRATE+ and LAUENORM (Wilkinson), (Campbell) for hexladi; SAINT (Bruker, 1998) for hex30x. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for hexladi, hex30x. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
Crystal data top
C30H22N4O8 | Z = 1 |
Mr = 566.00 | F(000) = 200.986 |
Triclinic, P1 | Dx = 1.525 Mg m−3 |
a = 7.3561 (2) Å | Neutron radiation, λ = 1.3102 Å |
b = 9.5856 (2) Å | Cell parameters from 2325 reflections |
c = 10.1478 (3) Å | θ = 5–55° |
α = 65.203 (2)° | µ = 0.17 mm−1 |
β = 72.699 (3)° | T = 20 K |
γ = 77.099 (3)° | Prism, colourless |
V = 616.16 (3) Å3 | 4.5 × 1.2 × 0.75 mm |
Data collection top
D19 diffractometer | 1743 reflections with I > 2σ(I) |
Radiation source: ILL high flux reactor | Rint = 0.023 |
Germanium (115) monochromator | θmax = 56.3°, θmin = 4.2° |
ω scans | h = −9→9 |
Absorption correction: gaussian D19ABS (Matthewmann et al, 1982) | k = −12→6 |
Tmin = 0.602, Tmax = 0.892 | l = −12→12 |
2464 measured reflections | 2 standard reflections every 75 reflections |
1866 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: X-Ray structure |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0471P)2 + 1.8319P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max = 0.001 |
S = 1.16 | Δρmax = 0.52 e Å−3 |
1866 reflections | Δρmin = −0.57 e Å−3 |
290 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0052 (5) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.58665 (19) | 0.58090 (16) | −0.14904 (14) | 0.0041 (3) | |
C10 | 0.6740 (2) | 0.67889 (15) | −0.30727 (14) | 0.0043 (3) | |
O11 | 0.6249 (2) | 0.81769 (18) | −0.35625 (16) | 0.0079 (3) | |
O12 | 0.8029 (2) | 0.60369 (18) | −0.38215 (16) | 0.0066 (3) | |
C2 | 0.39134 (19) | 0.55951 (16) | −0.10856 (14) | 0.0040 (3) | |
C20 | 0.2751 (2) | 0.61852 (15) | −0.22570 (14) | 0.0048 (3) | |
O21 | 0.1041 (2) | 0.66784 (19) | −0.19595 (16) | 0.0081 (3) | |
O22 | 0.3705 (2) | 0.60894 (19) | −0.35073 (16) | 0.0068 (3) | |
H2 | 0.8232 (4) | 0.6725 (4) | −0.4988 (3) | 0.0178 (6) | |
C3 | 0.3056 (2) | 0.47917 (16) | 0.04059 (14) | 0.0050 (3) | |
H3 | 0.1545 (4) | 0.4613 (4) | 0.0721 (3) | 0.0189 (6) | |
N1 | 0.28533 (14) | 0.77383 (11) | −0.59816 (10) | 0.0060 (2) | |
H1 | 0.3100 (5) | 0.6951 (4) | −0.4746 (3) | 0.0209 (6) | |
C11 | 0.3550 (2) | 0.71661 (16) | −0.70593 (14) | 0.0064 (3) | |
H11 | 0.4251 (5) | 0.5982 (3) | −0.6727 (3) | 0.0216 (7) | |
C12 | 0.3366 (2) | 0.80495 (16) | −0.85091 (14) | 0.0057 (3) | |
H12 | 0.3948 (5) | 0.7518 (4) | −0.9329 (3) | 0.0230 (7) | |
C13 | 0.24495 (19) | 0.95648 (15) | −0.88721 (14) | 0.0043 (3) | |
C14 | 0.1754 (2) | 1.01320 (16) | −0.77242 (14) | 0.0063 (3) | |
H14 | 0.1036 (5) | 1.1303 (3) | −0.7911 (3) | 0.0220 (7) | |
C15 | 0.1994 (2) | 0.91871 (16) | −0.62992 (14) | 0.0065 (3) | |
H15 | 0.1538 (5) | 0.9598 (4) | −0.5390 (3) | 0.0231 (7) | |
C21 | 0.2778 (2) | 1.09077 (16) | −1.30061 (14) | 0.0065 (3) | |
H21 | 0.3382 (5) | 1.0512 (4) | −1.3925 (3) | 0.0226 (7) | |
C22 | 0.3019 (2) | 0.99816 (16) | −1.15745 (14) | 0.0060 (3) | |
H22 | 0.3814 (5) | 0.8852 (3) | −1.1410 (3) | 0.0230 (7) | |
C23 | 0.22345 (19) | 1.05375 (15) | −1.04229 (13) | 0.0043 (3) | |
C24 | 0.1247 (2) | 1.20336 (16) | −1.07930 (14) | 0.0061 (3) | |
H24 | 0.0579 (5) | 1.2542 (4) | −0.9957 (3) | 0.0212 (7) | |
C25 | 0.1081 (2) | 1.28894 (16) | −1.22600 (14) | 0.0058 (3) | |
H25 | 0.0339 (5) | 1.4057 (3) | −1.2582 (3) | 0.0230 (7) | |
N2 | 0.18212 (14) | 1.23369 (11) | −1.33506 (10) | 0.0061 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0053 (6) | 0.0034 (6) | 0.0037 (5) | −0.0012 (5) | −0.0016 (5) | −0.0008 (5) |
C10 | 0.0060 (6) | 0.0031 (6) | 0.0033 (5) | −0.0033 (6) | 0.0005 (5) | −0.0004 (5) |
O11 | 0.0121 (7) | 0.0038 (7) | 0.0060 (6) | −0.0006 (7) | −0.0002 (6) | −0.0015 (6) |
O12 | 0.0073 (7) | 0.0048 (7) | 0.0057 (7) | −0.0005 (7) | 0.0003 (6) | −0.0015 (6) |
C2 | 0.0043 (6) | 0.0042 (6) | 0.0040 (6) | −0.0010 (5) | −0.0016 (5) | −0.0013 (5) |
C20 | 0.0060 (6) | 0.0044 (6) | 0.0045 (5) | 0.0003 (6) | −0.0017 (5) | −0.0023 (5) |
O21 | 0.0066 (7) | 0.0105 (8) | 0.0080 (6) | 0.0010 (7) | −0.0024 (6) | −0.0049 (6) |
O22 | 0.0078 (7) | 0.0078 (7) | 0.0047 (6) | 0.0014 (7) | −0.0023 (6) | −0.0029 (6) |
H2 | 0.0165 (13) | 0.0187 (14) | 0.0171 (14) | −0.0033 (13) | −0.0002 (11) | −0.0077 (13) |
C3 | 0.0053 (6) | 0.0062 (6) | 0.0037 (6) | −0.0018 (6) | −0.0008 (5) | −0.0016 (5) |
H3 | 0.0101 (13) | 0.0271 (16) | 0.0175 (12) | −0.0067 (13) | −0.0032 (11) | −0.0044 (12) |
N1 | 0.0073 (4) | 0.0056 (5) | 0.0057 (4) | −0.0004 (4) | −0.0023 (4) | −0.0024 (4) |
H1 | 0.0214 (15) | 0.0212 (16) | 0.0241 (15) | −0.0026 (14) | −0.0051 (12) | −0.0124 (13) |
C11 | 0.0090 (7) | 0.0045 (7) | 0.0056 (6) | −0.0005 (6) | −0.0016 (5) | −0.0020 (5) |
H11 | 0.0314 (17) | 0.0133 (15) | 0.0197 (13) | 0.0045 (14) | −0.0099 (13) | −0.0066 (12) |
C12 | 0.0089 (7) | 0.0037 (6) | 0.0050 (6) | 0.0012 (6) | −0.0025 (5) | −0.0023 (5) |
H12 | 0.0350 (18) | 0.0186 (14) | 0.0175 (13) | 0.0069 (14) | −0.0087 (13) | −0.0121 (12) |
C13 | 0.0050 (6) | 0.0038 (6) | 0.0044 (6) | 0.0001 (5) | −0.0015 (5) | −0.0018 (5) |
C14 | 0.0097 (6) | 0.0035 (7) | 0.0053 (6) | 0.0023 (6) | −0.0023 (5) | −0.0025 (5) |
H14 | 0.0330 (17) | 0.0114 (14) | 0.0207 (13) | 0.0064 (14) | −0.0081 (13) | −0.0084 (12) |
C15 | 0.0094 (6) | 0.0059 (7) | 0.0049 (6) | 0.0014 (6) | −0.0031 (5) | −0.0030 (5) |
H15 | 0.0345 (18) | 0.0234 (15) | 0.0148 (12) | 0.0031 (15) | −0.0078 (12) | −0.0121 (12) |
C21 | 0.0101 (6) | 0.0053 (7) | 0.0041 (6) | 0.0002 (6) | −0.0017 (5) | −0.0024 (5) |
H21 | 0.0332 (17) | 0.0198 (15) | 0.0145 (13) | 0.0059 (14) | −0.0048 (13) | −0.0111 (12) |
C22 | 0.0087 (7) | 0.0044 (7) | 0.0046 (6) | 0.0012 (6) | −0.0014 (5) | −0.0024 (5) |
H22 | 0.0333 (18) | 0.0131 (15) | 0.0193 (13) | 0.0076 (14) | −0.0076 (13) | −0.0070 (12) |
C23 | 0.0059 (6) | 0.0037 (7) | 0.0040 (6) | −0.0003 (6) | −0.0006 (5) | −0.0025 (5) |
C24 | 0.0090 (6) | 0.0043 (6) | 0.0050 (6) | 0.0009 (6) | −0.0020 (5) | −0.0023 (5) |
H24 | 0.0301 (16) | 0.0187 (15) | 0.0165 (13) | 0.0052 (14) | −0.0057 (12) | −0.0122 (12) |
C25 | 0.0073 (6) | 0.0039 (7) | 0.0054 (6) | −0.0012 (6) | −0.0002 (5) | −0.0015 (5) |
H25 | 0.0326 (18) | 0.0137 (15) | 0.0218 (13) | 0.0065 (15) | −0.0104 (13) | −0.0077 (12) |
N2 | 0.0078 (5) | 0.0064 (5) | 0.0041 (4) | −0.0006 (4) | −0.0014 (4) | −0.0020 (4) |
Geometric parameters (Å, º) top
C1—C3i | 1.3978 (19) | C12—C13 | 1.4007 (18) |
C1—C2 | 1.409 (2) | C12—H12 | 1.087 (3) |
C1—C10 | 1.5047 (17) | C13—C14 | 1.4024 (17) |
C10—O11 | 1.219 (2) | C13—C23 | 1.4907 (18) |
C10—O12 | 1.312 (2) | C14—C15 | 1.3873 (18) |
O12—H2 | 1.069 (3) | C14—H14 | 1.091 (3) |
C2—C3 | 1.3975 (17) | C15—H15 | 1.086 (3) |
C2—C20 | 1.5131 (18) | C21—N2 | 1.3449 (16) |
C20—O21 | 1.235 (2) | C21—C22 | 1.3895 (18) |
C20—O22 | 1.2845 (19) | C21—H21 | 1.088 (3) |
O22—H1 | 1.325 (3) | C22—C23 | 1.4023 (17) |
C3—C1i | 1.3978 (19) | C22—H22 | 1.080 (3) |
C3—H3 | 1.093 (3) | C23—C24 | 1.4039 (19) |
N1—C15 | 1.3364 (16) | C24—C25 | 1.3939 (18) |
N1—C11 | 1.3431 (15) | C24—H24 | 1.091 (3) |
N1—H1 | 1.207 (3) | C25—N2 | 1.3440 (15) |
C11—C12 | 1.3865 (18) | C25—H25 | 1.088 (3) |
C11—H11 | 1.090 (3) | | |
| | | |
C3i—C1—C2 | 120.08 (12) | C12—C13—C14 | 117.47 (11) |
C3i—C1—C10 | 120.33 (12) | C12—C13—C23 | 121.12 (11) |
C2—C1—C10 | 119.43 (12) | C14—C13—C23 | 121.41 (11) |
O11—C10—O12 | 124.96 (14) | C15—C14—C13 | 119.39 (12) |
O11—C10—C1 | 119.99 (12) | C15—C14—H14 | 118.29 (19) |
O12—C10—C1 | 115.05 (12) | C13—C14—H14 | 122.3 (2) |
C10—O12—H2 | 109.2 (2) | N1—C15—C14 | 121.81 (11) |
C3—C2—C1 | 119.68 (12) | N1—C15—H15 | 116.3 (2) |
C3—C2—C20 | 119.68 (12) | C14—C15—H15 | 121.8 (2) |
C1—C2—C20 | 120.61 (12) | N2—C21—C22 | 122.81 (11) |
O21—C20—O22 | 126.11 (15) | N2—C21—H21 | 116.0 (2) |
O21—C20—C2 | 120.17 (12) | C22—C21—H21 | 121.2 (2) |
O22—C20—C2 | 113.71 (12) | C21—C22—C23 | 119.51 (12) |
C20—O22—H1 | 120.32 (18) | C21—C22—H22 | 117.3 (2) |
C2—C3—C1i | 120.24 (13) | C23—C22—H22 | 123.2 (2) |
C2—C3—H3 | 119.81 (19) | C22—C23—C24 | 117.34 (11) |
C1i—C3—H3 | 119.9 (2) | C22—C23—C13 | 120.78 (11) |
C15—N1—C11 | 120.22 (10) | C24—C23—C13 | 121.88 (11) |
C15—N1—H1 | 120.78 (16) | C25—C24—C23 | 119.47 (12) |
C11—N1—H1 | 118.89 (17) | C25—C24—H24 | 118.8 (2) |
N1—C11—C12 | 120.97 (12) | C23—C24—H24 | 121.7 (2) |
N1—C11—H11 | 116.42 (19) | N2—C25—C24 | 122.62 (12) |
C12—C11—H11 | 122.61 (19) | N2—C25—H25 | 116.29 (19) |
C11—C12—C13 | 120.12 (12) | C24—C25—H25 | 121.1 (2) |
C11—C12—H12 | 117.5 (2) | C25—N2—C21 | 118.24 (10) |
C13—C12—H12 | 122.4 (2) | | |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O22 | 1.206 (3) | 1.325 (3) | 2.5217 (18) | 169.6 (3) |
O12—H2···N2ii | 1.068 (3) | 1.551 (3) | 2.6103 (17) | 170.1 (3) |
Symmetry code: (ii) −x+1, −y+2, −z−2. |
Crystal data top
C30H22N4O8 | Z = 1 |
Mr = 566.00 | F(000) = 200.986 |
Triclinic, P1 | Dx = 1.478 Mg m−3 |
a = 7.5011 (2) Å | Neutron radiation, λ = 1.302 Å |
b = 9.7868 (3) Å | Cell parameters from 2509 reflections |
c = 10.2303 (3) Å | θ = 3–55° |
α = 64.140 (3)° | µ = 0.17 mm−1 |
β = 71.682 (3)° | T = 293 K |
γ = 75.516 (3)° | Prism, colourless |
V = 635.93 (4) Å3 | 4.5 × 1.2 × 0.75 mm |
Data collection top
D19 diffractometer | 1894 reflections with I > 2σ(I) |
Radiation source: ILL High flux reactor | Rint = 0.028 |
Germanium (115) monochromator | θmax = 55.5°, θmin = 4.2° |
ω scans | h = −9→9 |
Absorption correction: gaussian D19ABS (Matthewmann et al, 1982) | k = −12→4 |
Tmin = 0.602, Tmax = 0.892 | l = −12→12 |
2914 measured reflections | 2 standard reflections every 70 reflections |
2145 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: X-Ray Structure |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0417P)2 + 1.6198P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max = 0.023 |
S = 1.05 | Δρmax = 0.43 e Å−3 |
2145 reflections | Δρmin = −0.43 e Å−3 |
291 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0066 (6) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.41579 (17) | 0.41855 (14) | 0.14981 (13) | 0.0252 (3) | |
C10 | 0.3285 (2) | 0.32047 (15) | 0.30805 (13) | 0.0293 (3) | |
O11 | 0.3785 (4) | 0.1839 (2) | 0.3567 (2) | 0.0530 (6) | |
O12 | 0.1992 (2) | 0.3939 (2) | 0.38196 (17) | 0.0367 (4) | |
H2 | 0.1780 (4) | 0.3249 (4) | 0.4998 (4) | 0.0509 (7) | |
C2 | 0.60671 (17) | 0.44024 (14) | 0.10818 (13) | 0.0242 (3) | |
C20 | 0.72238 (18) | 0.38061 (15) | 0.22366 (14) | 0.0282 (3) | |
O21 | 0.8909 (2) | 0.3350 (3) | 0.1937 (2) | 0.0492 (5) | |
O22 | 0.6282 (3) | 0.3887 (2) | 0.34904 (18) | 0.0434 (5) | |
C3 | 0.69031 (18) | 0.52122 (15) | −0.04139 (13) | 0.0264 (3) | |
H3 | 0.8373 (4) | 0.5392 (4) | −0.0727 (3) | 0.0475 (7) | |
N1 | 0.28131 (15) | −0.22432 (12) | 1.40422 (11) | 0.0353 (3) | |
H1 | 0.3116 (5) | −0.3078 (4) | 1.5369 (4) | 0.0581 (8) | |
C11 | 0.2025 (3) | −0.07861 (19) | 1.36857 (17) | 0.0447 (4) | |
H11 | 0.1600 (9) | −0.0374 (6) | 1.4578 (4) | 0.0912 (17) | |
C12 | 0.1801 (2) | 0.01558 (18) | 1.22540 (16) | 0.0416 (4) | |
H12 | 0.1126 (8) | 0.1331 (5) | 1.2044 (4) | 0.0844 (16) | |
C13 | 0.24339 (17) | −0.04221 (15) | 1.11355 (13) | 0.0258 (3) | |
C14 | 0.3280 (2) | −0.19436 (17) | 1.15343 (16) | 0.0382 (4) | |
H14 | 0.3815 (9) | −0.2474 (5) | 1.0734 (4) | 0.0869 (17) | |
C15 | 0.3450 (3) | −0.28168 (17) | 1.29888 (17) | 0.0406 (4) | |
H15 | 0.4098 (8) | −0.4002 (4) | 1.3334 (4) | 0.0782 (13) | |
C21 | 0.1128 (2) | 0.28835 (17) | 0.77215 (15) | 0.0371 (3) | |
H21 | 0.0405 (7) | 0.4055 (4) | 0.7373 (4) | 0.0692 (11) | |
C22 | 0.1290 (2) | 0.20355 (16) | 0.91907 (15) | 0.0345 (3) | |
H22 | 0.0651 (6) | 0.2552 (4) | 1.0004 (4) | 0.0656 (11) | |
C23 | 0.22317 (17) | 0.05442 (14) | 0.95848 (13) | 0.0260 (3) | |
C24 | 0.2977 (2) | −0.00191 (17) | 0.84542 (15) | 0.0378 (4) | |
H24 | 0.3755 (7) | −0.1154 (4) | 0.8643 (4) | 0.0758 (13) | |
C25 | 0.2749 (2) | 0.08987 (18) | 0.70220 (15) | 0.0405 (4) | |
H25 | 0.3339 (7) | 0.0500 (5) | 0.6118 (4) | 0.0744 (13) | |
N2 | 0.18361 (15) | 0.23219 (12) | 0.66549 (10) | 0.0357 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0312 (6) | 0.0272 (6) | 0.0131 (5) | −0.0036 (5) | −0.0054 (5) | −0.0041 (5) |
C10 | 0.0405 (7) | 0.0266 (6) | 0.0142 (6) | −0.0040 (6) | −0.0046 (5) | −0.0035 (5) |
O11 | 0.0898 (15) | 0.0269 (8) | 0.0235 (8) | −0.0048 (10) | 0.0010 (9) | −0.0045 (7) |
O12 | 0.0373 (8) | 0.0392 (8) | 0.0196 (7) | 0.0039 (7) | −0.0036 (6) | −0.0058 (7) |
H2 | 0.0447 (14) | 0.0540 (18) | 0.0445 (18) | −0.0038 (14) | 0.0006 (13) | −0.0196 (16) |
C2 | 0.0298 (6) | 0.0263 (6) | 0.0135 (5) | −0.0011 (5) | −0.0077 (5) | −0.0047 (5) |
C20 | 0.0331 (6) | 0.0296 (6) | 0.0185 (6) | 0.0053 (5) | −0.0116 (5) | −0.0076 (5) |
O21 | 0.0350 (8) | 0.0752 (14) | 0.0355 (9) | 0.0126 (9) | −0.0164 (7) | −0.0249 (10) |
O22 | 0.0473 (9) | 0.0565 (11) | 0.0218 (7) | 0.0154 (8) | −0.0175 (7) | −0.0165 (8) |
C3 | 0.0298 (6) | 0.0306 (6) | 0.0145 (5) | −0.0035 (5) | −0.0065 (5) | −0.0043 (5) |
H3 | 0.0377 (14) | 0.0612 (18) | 0.0346 (14) | −0.0110 (13) | −0.0054 (11) | −0.0104 (14) |
N1 | 0.0441 (5) | 0.0375 (5) | 0.0221 (4) | −0.0003 (5) | −0.0156 (4) | −0.0070 (4) |
H1 | 0.0549 (17) | 0.064 (2) | 0.060 (2) | −0.0034 (16) | −0.0143 (16) | −0.0301 (19) |
C11 | 0.0638 (10) | 0.0438 (9) | 0.0248 (7) | 0.0114 (8) | −0.0191 (7) | −0.0157 (7) |
H11 | 0.148 (4) | 0.081 (3) | 0.045 (2) | 0.037 (3) | −0.043 (2) | −0.038 (2) |
C12 | 0.0618 (9) | 0.0355 (8) | 0.0245 (7) | 0.0136 (7) | −0.0189 (7) | −0.0137 (6) |
H12 | 0.145 (4) | 0.051 (2) | 0.051 (2) | 0.040 (2) | −0.046 (2) | −0.0277 (18) |
C13 | 0.0312 (6) | 0.0265 (6) | 0.0181 (6) | −0.0007 (5) | −0.0089 (5) | −0.0067 (5) |
C14 | 0.0601 (9) | 0.0284 (7) | 0.0247 (7) | 0.0062 (7) | −0.0181 (7) | −0.0098 (6) |
H14 | 0.162 (5) | 0.0503 (19) | 0.0427 (18) | 0.032 (3) | −0.042 (2) | −0.0249 (17) |
C15 | 0.0627 (9) | 0.0301 (8) | 0.0257 (7) | 0.0034 (7) | −0.0201 (7) | −0.0063 (6) |
H15 | 0.135 (4) | 0.0414 (19) | 0.0497 (19) | 0.017 (2) | −0.045 (2) | −0.0101 (16) |
C21 | 0.0435 (7) | 0.0330 (8) | 0.0216 (6) | 0.0058 (7) | −0.0090 (6) | −0.0038 (6) |
H21 | 0.096 (3) | 0.0454 (19) | 0.0443 (17) | 0.027 (2) | −0.0251 (19) | −0.0114 (16) |
C22 | 0.0439 (7) | 0.0314 (7) | 0.0216 (6) | 0.0055 (6) | −0.0110 (6) | −0.0078 (6) |
H22 | 0.102 (3) | 0.0486 (17) | 0.0371 (16) | 0.0215 (19) | −0.0218 (18) | −0.0211 (15) |
C23 | 0.0316 (6) | 0.0260 (6) | 0.0178 (6) | 0.0005 (5) | −0.0084 (5) | −0.0068 (5) |
C24 | 0.0543 (8) | 0.0321 (8) | 0.0194 (6) | 0.0040 (7) | −0.0088 (6) | −0.0083 (6) |
H24 | 0.123 (3) | 0.0470 (19) | 0.0419 (18) | 0.030 (2) | −0.027 (2) | −0.0197 (16) |
C25 | 0.0571 (9) | 0.0388 (8) | 0.0184 (6) | 0.0030 (7) | −0.0100 (6) | −0.0089 (6) |
H25 | 0.116 (3) | 0.067 (2) | 0.0290 (15) | 0.015 (2) | −0.0186 (19) | −0.0227 (16) |
N2 | 0.0413 (5) | 0.0381 (5) | 0.0177 (4) | −0.0008 (5) | −0.0069 (4) | −0.0043 (4) |
Geometric parameters (Å, º) top
C1—C3i | 1.4003 (18) | C12—C13 | 1.394 (2) |
C1—C2 | 1.4026 (19) | C12—H12 | 1.089 (4) |
C1—C10 | 1.505 (2) | C13—C14 | 1.395 (2) |
C10—O11 | 1.209 (2) | C13—C23 | 1.485 (2) |
C10—O12 | 1.301 (2) | C14—C15 | 1.384 (2) |
O12—H2 | 1.076 (4) | C14—H14 | 1.077 (4) |
C2—C3 | 1.3966 (19) | C15—H15 | 1.084 (4) |
C2—C20 | 1.5095 (18) | C21—N2 | 1.3370 (19) |
C20—O21 | 1.219 (2) | C21—C22 | 1.392 (2) |
C20—O22 | 1.281 (2) | C21—H21 | 1.090 (4) |
C3—C1i | 1.4003 (18) | C22—C23 | 1.393 (2) |
C3—H3 | 1.084 (3) | C22—H22 | 1.083 (4) |
N1—C15 | 1.332 (2) | C23—C24 | 1.396 (2) |
N1—C11 | 1.333 (2) | C24—C25 | 1.384 (2) |
N1—H1 | 1.302 (4) | C24—H24 | 1.082 (4) |
C11—C12 | 1.386 (2) | C25—N2 | 1.334 (2) |
C11—H11 | 1.082 (4) | C25—H25 | 1.083 (4) |
| | | |
C3i—C1—C2 | 119.87 (12) | C12—C13—C14 | 117.07 (13) |
C3i—C1—C10 | 119.63 (12) | C12—C13—C23 | 121.43 (12) |
C2—C1—C10 | 120.32 (11) | C14—C13—C23 | 121.49 (12) |
O11—C10—O12 | 125.08 (17) | C15—C14—C13 | 120.21 (14) |
O11—C10—C1 | 119.94 (15) | C15—C14—H14 | 118.1 (2) |
O12—C10—C1 | 114.98 (13) | C13—C14—H14 | 121.7 (2) |
C10—O12—H2 | 109.5 (2) | N1—C15—C14 | 121.57 (14) |
C3—C2—C1 | 119.80 (11) | N1—C15—H15 | 116.4 (2) |
C3—C2—C20 | 119.32 (12) | C14—C15—H15 | 122.0 (3) |
C1—C2—C20 | 120.86 (11) | N2—C21—C22 | 122.58 (13) |
O21—C20—O22 | 125.25 (15) | N2—C21—H21 | 115.9 (2) |
O21—C20—C2 | 120.99 (14) | C22—C21—H21 | 121.6 (2) |
O22—C20—C2 | 113.72 (13) | C21—C22—C23 | 119.60 (14) |
C2—C3—C1i | 120.32 (12) | C21—C22—H22 | 118.7 (2) |
C2—C3—H3 | 119.52 (19) | C23—C22—H22 | 121.7 (2) |
C1i—C3—H3 | 120.1 (2) | C22—C23—C24 | 117.07 (12) |
C15—N1—C11 | 119.41 (12) | C22—C23—C13 | 122.10 (12) |
C15—N1—H1 | 119.20 (19) | C24—C23—C13 | 120.83 (12) |
C11—N1—H1 | 121.13 (19) | C25—C24—C23 | 119.68 (13) |
N1—C11—C12 | 122.23 (14) | C25—C24—H24 | 117.7 (2) |
N1—C11—H11 | 115.8 (3) | C23—C24—H24 | 122.7 (2) |
C12—C11—H11 | 122.0 (3) | N2—C25—C24 | 122.93 (14) |
C11—C12—C13 | 119.48 (14) | N2—C25—H25 | 115.8 (2) |
C11—C12—H12 | 118.4 (2) | C24—C25—H25 | 121.2 (3) |
C13—C12—H12 | 122.1 (2) | C25—N2—C21 | 118.15 (12) |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O22ii | 1.301 (4) | 1.240 (4) | 2.531 (3) | 169.4 (3) |
O12—H2···N2 | 1.076 (4) | 1.543 (4) | 2.608 (3) | 169.5 (3) |
Symmetry code: (ii) −x+1, −y, −z+2. |
Crystal data top
C30H22N4O8 | V = 635.9 (5) Å3 |
Mr = 566.00 | Z = 1 |
Triclinic, P1 | F(000) = 201 |
a = 7.541 (1) Å | Dx = 1.478 Mg m−3 |
b = 9.715 (1) Å | Neutron radiation, λ = 1.1 to 1.9 Å |
c = 10.204 (1) Å | µ = 0.00 mm−1 |
α = 64.51 (1)° | T = 200 K |
β = 72.03 (1)° | Plate, colourless |
γ = 76.08 (1)° | 1.3 × 0.6 × 0.2 mm |
Data collection top
LADI Laue diffractometer | 1192 reflections with I > 2σ(I) |
Radiation source: ILL high flux reactor | Rint = 0.113 |
Graphite monochromator | θmax = 30.7°, θmin = 3.2° |
Laue method scans | h = −7→7 |
1961 measured reflections | k = −12→13 |
1961 independent reflections | l = 0→14 |
Refinement top
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.125 | All H-atom parameters refined |
S = 1.28 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
1961 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.2833 (3) | −0.2257 (2) | 1.40362 (18) | 0.0241 (8) | |
H1 | 0.3112 (10) | −0.3049 (7) | 1.5310 (7) | 0.040 (2) | |
C11 | 0.3482 (5) | −0.2825 (3) | 1.2972 (3) | 0.0263 (11) | |
H11 | 0.4182 (12) | −0.3988 (6) | 1.3279 (7) | 0.052 (3) | |
C12 | 0.3314 (5) | −0.1950 (3) | 1.1524 (2) | 0.0263 (10) | |
H12 | 0.3858 (13) | −0.2476 (7) | 1.0715 (6) | 0.063 (3) | |
C13 | 0.2439 (4) | −0.0427 (3) | 1.1136 (2) | 0.0156 (9) | |
C14 | 0.1779 (5) | 0.0143 (3) | 1.2266 (2) | 0.0290 (11) | |
H14 | 0.1083 (12) | 0.1306 (7) | 1.2078 (6) | 0.057 (3) | |
C15 | 0.2001 (5) | −0.0801 (3) | 1.3691 (3) | 0.0303 (12) | |
H15 | 0.1555 (13) | −0.0405 (8) | 1.4585 (6) | 0.065 (3) | |
C21 | 0.2757 (5) | 0.0899 (3) | 0.7012 (3) | 0.0278 (11) | |
H21 | 0.3353 (11) | 0.0490 (7) | 0.6103 (6) | 0.047 (2) | |
C22 | 0.2985 (5) | −0.0020 (3) | 0.8441 (2) | 0.0237 (10) | |
H22 | 0.3791 (11) | −0.1135 (7) | 0.8629 (6) | 0.053 (3) | |
C23 | 0.2240 (4) | 0.0544 (3) | 0.9585 (2) | 0.0182 (10) | |
C24 | 0.1266 (5) | 0.2036 (3) | 0.9205 (2) | 0.0244 (10) | |
H24 | 0.0626 (12) | 0.2548 (6) | 1.0017 (6) | 0.047 (2) | |
C25 | 0.1108 (5) | 0.2893 (3) | 0.7726 (2) | 0.0230 (10) | |
H25 | 0.0379 (10) | 0.4051 (6) | 0.7397 (6) | 0.049 (2) | |
N2 | 0.1829 (3) | 0.2332 (2) | 0.66540 (17) | 0.0246 (8) | |
C1 | 0.5845 (5) | −0.4190 (3) | 1.8510 (2) | 0.0179 (10) | |
C10 | 0.6712 (5) | −0.3215 (3) | 1.6921 (2) | 0.0202 (10) | |
O11 | 0.6213 (6) | −0.1824 (3) | 1.6424 (3) | 0.0376 (14) | |
O12 | 0.8030 (5) | −0.3952 (3) | 1.6176 (3) | 0.0243 (12) | |
H2 | 0.8212 (10) | −0.3257 (7) | 1.5017 (5) | 0.046 (2) | |
C2 | 0.3934 (5) | −0.4405 (3) | 1.8915 (2) | 0.0173 (10) | |
C20 | 0.2775 (5) | −0.3806 (3) | 1.7755 (2) | 0.0199 (10) | |
O21 | 0.1074 (6) | −0.3335 (4) | 1.8049 (3) | 0.0320 (13) | |
O22 | 0.3708 (6) | −0.3895 (4) | 1.6504 (3) | 0.0239 (12) | |
C3 | 0.3082 (6) | −0.5211 (3) | 2.0408 (2) | 0.0187 (12) | |
H3 | 0.1592 (13) | −0.5402 (7) | 2.0733 (7) | 0.034 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0271 (17) | 0.0294 (9) | 0.0156 (7) | −0.0007 (10) | −0.0117 (8) | −0.0056 (6) |
H1 | 0.035 (5) | 0.044 (3) | 0.045 (3) | −0.008 (3) | −0.008 (3) | −0.020 (3) |
C11 | 0.036 (3) | 0.0241 (13) | 0.0193 (11) | 0.0030 (14) | −0.0154 (12) | −0.0062 (9) |
H11 | 0.090 (7) | 0.025 (2) | 0.045 (3) | 0.014 (3) | −0.040 (4) | −0.012 (2) |
C12 | 0.040 (3) | 0.0215 (11) | 0.0159 (10) | 0.0054 (14) | −0.0129 (11) | −0.0064 (9) |
H12 | 0.104 (7) | 0.040 (3) | 0.031 (3) | 0.019 (4) | −0.016 (3) | −0.016 (2) |
C13 | 0.017 (2) | 0.0184 (10) | 0.0119 (9) | −0.0019 (12) | −0.0072 (10) | −0.0042 (8) |
C14 | 0.042 (3) | 0.0274 (13) | 0.0162 (10) | 0.0104 (14) | −0.0141 (12) | −0.0106 (9) |
H14 | 0.097 (7) | 0.038 (3) | 0.034 (3) | 0.026 (4) | −0.033 (3) | −0.018 (2) |
C15 | 0.041 (3) | 0.0319 (14) | 0.0172 (11) | 0.0097 (15) | −0.0145 (12) | −0.0113 (10) |
H15 | 0.102 (7) | 0.062 (4) | 0.029 (3) | 0.022 (4) | −0.027 (3) | −0.025 (3) |
C21 | 0.035 (2) | 0.0296 (13) | 0.0136 (10) | 0.0000 (14) | −0.0053 (11) | −0.0069 (9) |
H21 | 0.066 (6) | 0.049 (3) | 0.026 (2) | 0.006 (3) | −0.014 (3) | −0.022 (2) |
C22 | 0.028 (2) | 0.0269 (13) | 0.0152 (10) | 0.0028 (14) | −0.0102 (11) | −0.0076 (9) |
H22 | 0.075 (6) | 0.042 (3) | 0.035 (3) | 0.017 (4) | −0.019 (3) | −0.019 (2) |
C23 | 0.019 (2) | 0.0194 (11) | 0.0128 (9) | −0.0030 (13) | −0.0034 (10) | −0.0036 (8) |
C24 | 0.031 (2) | 0.0222 (12) | 0.0154 (10) | 0.0033 (13) | −0.0067 (11) | −0.0060 (9) |
H24 | 0.073 (6) | 0.036 (3) | 0.029 (2) | 0.012 (3) | −0.015 (3) | −0.019 (2) |
C25 | 0.025 (2) | 0.0245 (12) | 0.0166 (10) | 0.0016 (13) | −0.0094 (11) | −0.0045 (9) |
H25 | 0.054 (5) | 0.036 (3) | 0.040 (3) | 0.020 (3) | −0.023 (3) | −0.004 (2) |
N2 | 0.0264 (17) | 0.0295 (9) | 0.0128 (7) | 0.0003 (10) | −0.0060 (8) | −0.0047 (6) |
C1 | 0.018 (2) | 0.0236 (12) | 0.0099 (9) | −0.0011 (13) | −0.0049 (11) | −0.0039 (8) |
C10 | 0.024 (2) | 0.0231 (12) | 0.0119 (9) | −0.0042 (13) | −0.0051 (10) | −0.0039 (8) |
O11 | 0.061 (3) | 0.0206 (14) | 0.0174 (12) | −0.0034 (17) | 0.0018 (15) | −0.0041 (10) |
O12 | 0.021 (3) | 0.0284 (15) | 0.0165 (12) | −0.0002 (16) | −0.0034 (13) | −0.0053 (11) |
H2 | 0.046 (5) | 0.048 (3) | 0.030 (3) | 0.003 (3) | 0.000 (3) | −0.013 (2) |
C2 | 0.023 (3) | 0.0201 (11) | 0.0104 (9) | −0.0025 (13) | −0.0074 (11) | −0.0048 (8) |
C20 | 0.020 (2) | 0.0247 (12) | 0.0148 (10) | 0.0027 (13) | −0.0098 (11) | −0.0070 (9) |
O21 | 0.019 (3) | 0.053 (2) | 0.0252 (14) | 0.0061 (19) | −0.0135 (14) | −0.0164 (13) |
O22 | 0.023 (3) | 0.0371 (16) | 0.0166 (11) | 0.0032 (16) | −0.0147 (13) | −0.0117 (11) |
C3 | 0.020 (3) | 0.0224 (12) | 0.0109 (10) | −0.0061 (15) | −0.0033 (12) | −0.0030 (8) |
H3 | 0.016 (6) | 0.055 (4) | 0.036 (3) | −0.008 (4) | −0.011 (3) | −0.015 (3) |
Geometric parameters (Å, º) top
N1—C11 | 1.338 (3) | C24—C25 | 1.401 (3) |
N1—C15 | 1.341 (3) | C24—H24 | 1.079 (5) |
N1—H1 | 1.246 (6) | C25—N2 | 1.342 (3) |
C11—C12 | 1.379 (3) | C25—H25 | 1.082 (5) |
C11—H11 | 1.078 (5) | C1—C2 | 1.404 (5) |
C12—C13 | 1.403 (3) | C1—C3i | 1.406 (5) |
C12—H12 | 1.083 (6) | C1—C10 | 1.506 (3) |
C13—C14 | 1.399 (3) | C10—O11 | 1.230 (4) |
C13—C23 | 1.485 (3) | C10—O12 | 1.315 (3) |
C14—C15 | 1.382 (3) | O12—H2 | 1.062 (6) |
C14—H14 | 1.086 (5) | C2—C3 | 1.396 (3) |
C15—H15 | 1.072 (6) | C2—C20 | 1.515 (4) |
C21—N2 | 1.345 (3) | C20—O21 | 1.232 (5) |
C21—C22 | 1.381 (3) | C20—O22 | 1.281 (4) |
C21—H21 | 1.095 (5) | O22—H1 | 1.285 (7) |
C22—C23 | 1.409 (3) | C3—C1i | 1.406 (5) |
C22—H22 | 1.074 (5) | C3—H3 | 1.101 (13) |
C23—C24 | 1.402 (3) | | |
| | | |
C11—N1—C15 | 119.48 (19) | C22—C23—C13 | 120.93 (18) |
C11—N1—H1 | 119.8 (3) | C25—C24—C23 | 119.2 (2) |
C15—N1—H1 | 120.5 (3) | C25—C24—H24 | 118.6 (3) |
N1—C11—C12 | 121.6 (2) | C23—C24—H24 | 122.1 (3) |
N1—C11—H11 | 117.6 (4) | N2—C25—C24 | 122.4 (2) |
C12—C11—H11 | 120.8 (4) | N2—C25—H25 | 116.7 (4) |
C11—C12—C13 | 120.1 (2) | C24—C25—H25 | 120.9 (4) |
C11—C12—H12 | 118.1 (3) | C25—N2—C21 | 118.64 (18) |
C13—C12—H12 | 121.8 (3) | C2—C1—C3i | 120.6 (2) |
C14—C13—C12 | 117.3 (2) | C2—C1—C10 | 119.6 (2) |
C14—C13—C23 | 121.42 (19) | C3i—C1—C10 | 119.6 (3) |
C12—C13—C23 | 121.30 (19) | O11—C10—O12 | 124.7 (3) |
C15—C14—C13 | 119.4 (2) | O11—C10—C1 | 120.0 (2) |
C15—C14—H14 | 117.8 (4) | O12—C10—C1 | 115.3 (2) |
C13—C14—H14 | 122.8 (3) | C10—O12—H2 | 108.2 (4) |
N1—C15—C14 | 122.2 (2) | C3—C2—C1 | 119.9 (3) |
N1—C15—H15 | 115.8 (4) | C3—C2—C20 | 118.8 (3) |
C14—C15—H15 | 122.0 (4) | C1—C2—C20 | 121.2 (2) |
N2—C21—C22 | 122.6 (2) | O21—C20—O22 | 124.7 (3) |
N2—C21—H21 | 116.5 (4) | O21—C20—C2 | 121.2 (2) |
C22—C21—H21 | 120.9 (4) | O22—C20—C2 | 114.0 (3) |
C21—C22—C23 | 119.8 (2) | C20—O22—H1 | 120.2 (4) |
C21—C22—H22 | 118.2 (4) | C2—C3—C1i | 119.5 (4) |
C23—C22—H22 | 122.0 (4) | C2—C3—H3 | 120.4 (4) |
C24—C23—C22 | 117.3 (2) | C1i—C3—H3 | 120.1 (4) |
C24—C23—C13 | 121.77 (19) | | |
Symmetry code: (i) −x+1, −y−1, −z+4. |
Crystal data top
C30H22N4O8 | Z = 1 |
Mr = 566.52 | F(000) = 294 |
Triclinic, P1 | Dx = 1.526 Mg m−3 |
a = 7.357 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.587 (3) Å | Cell parameters from 1690 reflections |
c = 10.147 (3) Å | θ = 12.0–27.7° |
α = 65.256 (4)° | µ = 0.11 mm−1 |
β = 72.687 (4)° | T = 30 K |
γ = 77.052 (4)° | Block, colourless |
V = 616.4 (3) Å3 | 0.5 × 0.35 × 0.15 mm |
Data collection top
Bruker SMART-CCD diffractometer | 2126 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 27.6°, θmin = 2.3° |
ω scans | h = −9→9 |
5958 measured reflections | k = −12→12 |
2549 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | All H-atom parameters refined |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.66 | (Δ/σ)max < 0.001 |
2549 reflections | Δρmax = 0.35 e Å−3 |
235 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (3) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.58628 (18) | 0.58045 (14) | −0.14876 (13) | 0.0110 (3) | |
C10 | 0.67364 (18) | 0.67962 (15) | −0.30729 (14) | 0.0110 (3) | |
O11 | 0.62539 (13) | 0.81828 (10) | −0.35663 (10) | 0.0142 (2) | |
O12 | 0.80279 (12) | 0.60285 (10) | −0.38178 (10) | 0.0126 (2) | |
C2 | 0.39158 (18) | 0.55949 (14) | −0.10827 (14) | 0.0115 (3) | |
C20 | 0.27494 (18) | 0.61849 (14) | −0.22590 (14) | 0.0113 (3) | |
O21 | 0.10389 (13) | 0.66758 (10) | −0.19559 (10) | 0.0142 (2) | |
O22 | 0.37066 (13) | 0.60893 (10) | −0.35071 (9) | 0.0135 (2) | |
H2 | 0.820 (3) | 0.666 (2) | −0.490 (2) | 0.063 (7)* | |
C3 | 0.30654 (19) | 0.47936 (14) | 0.04044 (14) | 0.0112 (3) | |
H3 | 0.174 (2) | 0.4655 (16) | 0.0667 (16) | 0.012 (4)* | |
N1 | 0.28515 (15) | 0.77398 (12) | −0.59822 (12) | 0.0119 (2) | |
H1 | 0.309 (3) | 0.702 (2) | −0.481 (2) | 0.057 (6)* | |
C11 | 0.35504 (18) | 0.71648 (15) | −0.70591 (14) | 0.0126 (3) | |
H11 | 0.421 (2) | 0.6135 (17) | −0.6806 (16) | 0.010 (3)* | |
C12 | 0.33640 (18) | 0.80494 (15) | −0.85034 (15) | 0.0127 (3) | |
H12 | 0.391 (2) | 0.7556 (18) | −0.9235 (17) | 0.017 (4)* | |
C13 | 0.24500 (18) | 0.95646 (15) | −0.88697 (14) | 0.0115 (3) | |
C14 | 0.17579 (18) | 1.01331 (15) | −0.77263 (14) | 0.0129 (3) | |
H14 | 0.113 (2) | 1.1128 (18) | −0.7893 (16) | 0.013 (4)* | |
C15 | 0.19959 (18) | 0.91909 (15) | −0.63026 (14) | 0.0128 (3) | |
H15 | 0.159 (2) | 0.9551 (16) | −0.5478 (16) | 0.013 (4)* | |
C21 | 0.27741 (18) | 1.09086 (15) | −1.30019 (14) | 0.0126 (3) | |
H21 | 0.328 (2) | 1.0541 (16) | −1.3816 (16) | 0.012 (4)* | |
C22 | 0.30112 (18) | 0.99866 (15) | −1.15749 (14) | 0.0127 (3) | |
H22 | 0.376 (2) | 0.8999 (17) | −1.1445 (15) | 0.009 (3)* | |
C23 | 0.22327 (18) | 1.05401 (15) | −1.04257 (14) | 0.0111 (3) | |
C24 | 0.12511 (18) | 1.20308 (15) | −1.07942 (14) | 0.0125 (3) | |
H24 | 0.065 (2) | 1.2487 (16) | −1.0073 (15) | 0.009 (3)* | |
C25 | 0.10877 (18) | 1.28843 (15) | −1.22582 (14) | 0.0125 (3) | |
H25 | 0.0398 (19) | 1.3925 (16) | −1.2530 (15) | 0.009 (3)* | |
N2 | 0.18216 (15) | 1.23362 (13) | −1.33515 (12) | 0.0125 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0145 (6) | 0.0081 (6) | 0.0108 (6) | 0.0004 (5) | −0.0028 (5) | −0.0050 (5) |
C10 | 0.0102 (6) | 0.0133 (7) | 0.0115 (6) | −0.0020 (5) | −0.0050 (5) | −0.0046 (5) |
O11 | 0.0178 (5) | 0.0114 (5) | 0.0116 (4) | −0.0010 (4) | −0.0038 (4) | −0.0028 (4) |
O12 | 0.0130 (5) | 0.0141 (5) | 0.0089 (4) | −0.0001 (4) | −0.0019 (4) | −0.0040 (4) |
C2 | 0.0136 (6) | 0.0100 (6) | 0.0121 (6) | 0.0017 (5) | −0.0042 (5) | −0.0059 (5) |
C20 | 0.0143 (6) | 0.0084 (6) | 0.0117 (6) | −0.0020 (5) | −0.0037 (5) | −0.0034 (5) |
O21 | 0.0125 (5) | 0.0159 (5) | 0.0139 (5) | 0.0005 (4) | −0.0037 (4) | −0.0059 (4) |
O22 | 0.0145 (5) | 0.0156 (5) | 0.0096 (4) | 0.0007 (4) | −0.0036 (4) | −0.0047 (4) |
C3 | 0.0115 (6) | 0.0099 (6) | 0.0132 (6) | −0.0005 (5) | −0.0031 (5) | −0.0055 (5) |
N1 | 0.0116 (6) | 0.0128 (6) | 0.0114 (5) | −0.0024 (4) | −0.0036 (5) | −0.0036 (4) |
C11 | 0.0122 (6) | 0.0126 (7) | 0.0136 (6) | −0.0013 (5) | −0.0045 (5) | −0.0044 (5) |
C12 | 0.0115 (6) | 0.0150 (7) | 0.0133 (6) | −0.0021 (5) | −0.0026 (5) | −0.0068 (5) |
C13 | 0.0084 (6) | 0.0140 (7) | 0.0117 (6) | −0.0032 (5) | −0.0028 (5) | −0.0032 (5) |
C14 | 0.0120 (6) | 0.0118 (7) | 0.0144 (7) | −0.0008 (5) | −0.0034 (5) | −0.0046 (5) |
C15 | 0.0125 (6) | 0.0141 (7) | 0.0122 (6) | −0.0013 (5) | −0.0030 (5) | −0.0053 (5) |
C21 | 0.0128 (6) | 0.0146 (7) | 0.0108 (6) | −0.0017 (5) | −0.0032 (5) | −0.0048 (5) |
C22 | 0.0121 (6) | 0.0120 (7) | 0.0132 (6) | −0.0012 (5) | −0.0028 (5) | −0.0042 (5) |
C23 | 0.0091 (6) | 0.0136 (7) | 0.0107 (6) | −0.0039 (5) | −0.0021 (5) | −0.0036 (5) |
C24 | 0.0115 (6) | 0.0151 (7) | 0.0121 (6) | −0.0018 (5) | −0.0024 (5) | −0.0063 (5) |
C25 | 0.0108 (6) | 0.0119 (7) | 0.0141 (6) | −0.0010 (5) | −0.0029 (5) | −0.0043 (5) |
N2 | 0.0113 (5) | 0.0139 (6) | 0.0123 (5) | −0.0023 (4) | −0.0028 (4) | −0.0044 (4) |
Geometric parameters (Å, º) top
C1—C3i | 1.3943 (18) | C12—C13 | 1.3999 (18) |
C1—C2 | 1.4038 (19) | C12—H12 | 0.984 (15) |
C1—C10 | 1.5109 (17) | C13—C14 | 1.3984 (18) |
C10—O11 | 1.2170 (16) | C13—C23 | 1.4966 (18) |
C10—O12 | 1.3193 (15) | C14—C15 | 1.3860 (18) |
O12—H2 | 0.99 (2) | C14—H14 | 0.931 (15) |
C2—C3 | 1.3934 (18) | C15—H15 | 0.977 (14) |
C2—C20 | 1.5192 (17) | C21—N2 | 1.3424 (17) |
C20—O21 | 1.2350 (15) | C21—C22 | 1.3850 (18) |
C20—O22 | 1.2828 (15) | C21—H21 | 0.973 (14) |
O22—H1 | 1.40 (2) | C22—C23 | 1.3977 (17) |
C3—C1i | 1.3943 (18) | C22—H22 | 0.960 (14) |
C3—H3 | 0.957 (15) | C23—C24 | 1.3981 (18) |
N1—C15 | 1.3372 (16) | C24—C25 | 1.3912 (18) |
N1—C11 | 1.3435 (16) | C24—H24 | 0.954 (14) |
N1—H1 | 1.14 (2) | C25—N2 | 1.3425 (16) |
C11—C12 | 1.3831 (18) | C25—H25 | 0.977 (14) |
C11—H11 | 0.962 (14) | | |
| | | |
C3i—C1—C2 | 119.96 (12) | C14—C13—C12 | 117.36 (11) |
C3i—C1—C10 | 120.36 (12) | C14—C13—C23 | 121.35 (11) |
C2—C1—C10 | 119.47 (11) | C12—C13—C23 | 121.29 (11) |
O11—C10—O12 | 125.13 (12) | C15—C14—C13 | 119.40 (12) |
O11—C10—C1 | 120.63 (11) | C15—C14—H14 | 118.9 (9) |
O12—C10—C1 | 114.24 (11) | C13—C14—H14 | 121.7 (9) |
C10—O12—H2 | 108.7 (12) | N1—C15—C14 | 121.85 (12) |
C3—C2—C1 | 119.61 (11) | N1—C15—H15 | 115.7 (8) |
C3—C2—C20 | 119.81 (12) | C14—C15—H15 | 122.4 (8) |
C1—C2—C20 | 120.55 (11) | N2—C21—C22 | 123.01 (12) |
O21—C20—O22 | 126.45 (11) | N2—C21—H21 | 115.9 (8) |
O21—C20—C2 | 119.90 (11) | C22—C21—H21 | 121.1 (8) |
O22—C20—C2 | 113.64 (11) | C21—C22—C23 | 119.65 (12) |
C20—O22—H1 | 120.1 (8) | C21—C22—H22 | 116.8 (8) |
C2—C3—C1i | 120.43 (12) | C23—C22—H22 | 123.5 (8) |
C2—C3—H3 | 118.9 (8) | C22—C23—C24 | 117.23 (11) |
C1i—C3—H3 | 120.7 (8) | C22—C23—C13 | 120.85 (12) |
C15—N1—C11 | 120.20 (11) | C24—C23—C13 | 121.91 (11) |
C15—N1—H1 | 119.9 (10) | C25—C24—C23 | 119.47 (12) |
C11—N1—H1 | 119.8 (10) | C25—C24—H24 | 117.9 (8) |
N1—C11—C12 | 120.70 (12) | C23—C24—H24 | 122.6 (8) |
N1—C11—H11 | 118.4 (8) | N2—C25—C24 | 122.88 (12) |
C12—C11—H11 | 120.9 (8) | N2—C25—H25 | 116.8 (8) |
C11—C12—C13 | 120.47 (12) | C24—C25—H25 | 120.3 (8) |
C11—C12—H12 | 116.4 (9) | C21—N2—C25 | 117.75 (11) |
C13—C12—H12 | 123.1 (9) | | |
Symmetry code: (i) −x+1, −y+1, −z. |