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In the title compound, C
9H
9NO
3, the methoxycarbonyl group makes an angle of 18.59 (5)° with the seven-membered ring. The NH
2 group participates in intermolecular N—H
O hydrogen bonding with the O atoms of neighbouring molecules, and the crystal packing is consolidated by π–π, N—H
π and C—H
O interactions.
Supporting information
CCDC reference: 618337
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.109
- Data-to-parameter ratio = 11.3
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.641 0.868
Tmin(prime) and Tmax expected: 0.729 0.868
RR(prime) = 0.880
Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H1
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
Methyl 4-amino-5-oxocyclohepta-1,3,6-triene-1-carboxylate
top
Crystal data top
C9H9NO3 | F(000) = 752.00 |
Mr = 179.17 | Dx = 1.468 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 13350 reflections |
a = 11.113 (3) Å | θ = 4.0–68.2° |
b = 9.084 (3) Å | µ = 0.94 mm−1 |
c = 16.059 (4) Å | T = 153 K |
V = 1621.1 (8) Å3 | Prism, yellow |
Z = 8 | 0.30 × 0.24 × 0.15 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1348 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.641, Tmax = 0.868 | k = −10→10 |
13745 measured reflections | l = −19→19 |
1443 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.051P)2 + 1.2779P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.041 | (Δ/σ)max < 0.001 |
wR(F2) = 0.109 | Δρmax = 0.42 e Å−3 |
S = 1.07 | Δρmin = −0.37 e Å−3 |
1443 reflections | Extinction correction: SHELXL97 |
128 parameters | Extinction coefficient: 0.0034 (4) |
H atoms treated by a mixture of independent and constrained refinement | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The
weighted R-factor(wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.54341 (11) | −0.15682 (12) | 0.73343 (6) | 0.0275 (3) | |
O2 | 0.25764 (11) | 0.25631 (13) | 0.43912 (8) | 0.0302 (3) | |
O3 | 0.44343 (11) | 0.34246 (12) | 0.46263 (8) | 0.0274 (3) | |
N1 | 0.31465 (16) | −0.18133 (17) | 0.75413 (10) | 0.0276 (3) | |
C1 | 0.48195 (16) | −0.07468 (18) | 0.68719 (10) | 0.0218 (4) | |
C2 | 0.34912 (16) | −0.08862 (18) | 0.69472 (10) | 0.0222 (4) | |
C3 | 0.26147 (16) | −0.0180 (2) | 0.64675 (11) | 0.0259 (4) | |
C4 | 0.27222 (16) | 0.08311 (19) | 0.58241 (11) | 0.0253 (4) | |
C5 | 0.37349 (16) | 0.14965 (18) | 0.54909 (10) | 0.0215 (4) | |
C6 | 0.49244 (16) | 0.12517 (18) | 0.57481 (10) | 0.0224 (4) | |
C7 | 0.53779 (14) | 0.02893 (19) | 0.63300 (10) | 0.0223 (4) | |
C8 | 0.35028 (14) | 0.25233 (18) | 0.47871 (10) | 0.0226 (4) | |
C9 | 0.42352 (18) | 0.4464 (2) | 0.39554 (11) | 0.0288 (4) | |
H1 | 0.371 (2) | −0.228 (2) | 0.7838 (14) | 0.040 (6)* | |
H2 | 0.239 (2) | −0.194 (2) | 0.7666 (13) | 0.031 (5)* | |
H3 | 0.1810 | −0.0435 | 0.6605 | 0.031* | |
H4 | 0.1984 | 0.1112 | 0.5572 | 0.030* | |
H5 | 0.5510 | 0.1845 | 0.5477 | 0.027* | |
H6 | 0.6229 | 0.0322 | 0.6380 | 0.027* | |
H7 | 0.4493 | 0.4024 | 0.3427 | 0.035* | |
H8 | 0.4701 | 0.5361 | 0.4060 | 0.035* | |
H9 | 0.3377 | 0.4708 | 0.3925 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0251 (7) | 0.0294 (6) | 0.0280 (6) | 0.0015 (5) | −0.0041 (5) | 0.0033 (5) |
O2 | 0.0216 (7) | 0.0361 (7) | 0.0329 (6) | −0.0012 (5) | −0.0055 (5) | 0.0061 (5) |
O3 | 0.0243 (7) | 0.0286 (6) | 0.0292 (6) | −0.0045 (5) | −0.0038 (5) | 0.0070 (5) |
N1 | 0.0241 (9) | 0.0317 (8) | 0.0269 (7) | −0.0024 (6) | 0.0012 (6) | 0.0040 (6) |
C1 | 0.0223 (9) | 0.0234 (8) | 0.0198 (7) | 0.0014 (6) | −0.0017 (6) | −0.0055 (6) |
C2 | 0.0236 (9) | 0.0226 (8) | 0.0204 (7) | −0.0023 (6) | 0.0013 (6) | −0.0045 (6) |
C3 | 0.0181 (9) | 0.0321 (9) | 0.0276 (8) | −0.0028 (7) | 0.0024 (6) | 0.0008 (7) |
C4 | 0.0189 (9) | 0.0305 (8) | 0.0263 (8) | 0.0014 (7) | −0.0017 (6) | −0.0003 (7) |
C5 | 0.0200 (9) | 0.0227 (8) | 0.0219 (8) | 0.0002 (6) | 0.0002 (6) | −0.0037 (6) |
C6 | 0.0207 (9) | 0.0233 (8) | 0.0232 (8) | −0.0030 (6) | 0.0013 (6) | −0.0029 (6) |
C7 | 0.0163 (9) | 0.0266 (8) | 0.0242 (8) | 0.0005 (6) | −0.0010 (6) | −0.0036 (6) |
C8 | 0.0198 (9) | 0.0240 (8) | 0.0239 (8) | 0.0010 (6) | 0.0011 (7) | −0.0029 (6) |
C9 | 0.0313 (10) | 0.0273 (9) | 0.0279 (9) | −0.0012 (7) | −0.0010 (7) | 0.0054 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.255 (2) | C5—C8 | 1.488 (2) |
O2—C8 | 1.211 (2) | C6—C7 | 1.375 (2) |
O3—C8 | 1.345 (2) | N1—H1 | 0.90 (2) |
O3—C9 | 1.449 (2) | N1—H2 | 0.87 (2) |
N1—C2 | 1.329 (2) | C3—H3 | 0.950 |
C1—C2 | 1.486 (2) | C4—H4 | 0.950 |
C1—C7 | 1.424 (2) | C6—H5 | 0.950 |
C2—C3 | 1.398 (2) | C7—H6 | 0.950 |
C3—C4 | 1.388 (2) | C9—H7 | 0.980 |
C4—C5 | 1.385 (2) | C9—H8 | 0.980 |
C5—C6 | 1.403 (2) | C9—H9 | 0.980 |
| | | |
O1···O3i | 3.5746 (16) | C8···H5v | 3.402 |
O1···N1 | 2.574 (2) | C8···H6i | 3.207 |
O1···N1ii | 3.029 (2) | C8···H7 | 2.800 |
O1···C2 | 2.331 (2) | C8···H8 | 3.127 |
O1···C3ii | 3.341 (2) | C8···H8vii | 3.332 |
O1···C7 | 2.335 (2) | C8···H9 | 2.424 |
O1···C9iii | 3.494 (2) | C8···H9vi | 3.581 |
O1···C9i | 3.368 (2) | C9···H1xiii | 3.18 (2) |
O2···O3 | 2.2401 (17) | C9···H2iv | 3.58 (2) |
O2···N1iv | 3.152 (2) | C9···H3xi | 3.127 |
O2···C4 | 2.792 (2) | C9···H4xiv | 3.289 |
O2···C5 | 2.391 (2) | C9···H4xi | 3.190 |
O2···C6v | 3.146 (2) | C9···H5vii | 3.486 |
O2···C7v | 3.334 (2) | C9···H6v | 3.389 |
O2···C9 | 2.621 (2) | C9···H8vii | 3.403 |
O2···C9vi | 3.531 (2) | H1···O1 | 2.18 (2) |
O3···O1i | 3.5746 (16) | H1···O2ix | 2.89 (2) |
O3···O2 | 2.2401 (17) | H1···C1 | 2.42 (2) |
O3···O3vii | 3.3487 (16) | H1···C1x | 3.57 (2) |
O3···C1i | 3.520 (2) | H1···C2 | 1.93 (2) |
O3···C4 | 3.588 (2) | H1···C3 | 3.16 (2) |
O3···C5 | 2.366 (2) | H1···C6x | 3.04 (2) |
O3···C6 | 2.727 (2) | H1···C7x | 2.77 (2) |
O3···C9vii | 3.325 (2) | H1···C9iii | 3.18 (2) |
N1···O1 | 2.574 (2) | H1···H2 | 1.52 (3) |
N1···O1viii | 3.029 (2) | H1···H3 | 3.347 |
N1···O2ix | 3.152 (2) | H1···H3vi | 3.529 |
N1···C1 | 2.356 (2) | H1···H5x | 2.949 |
N1···C3 | 2.350 (2) | H1···H6x | 2.512 |
N1···C7x | 3.592 (2) | H1···H7iii | 3.227 |
N1···C9iii | 3.343 (2) | H1···H7i | 3.257 |
C1···O3i | 3.520 (2) | H1···H8iii | 2.848 |
C1···N1 | 2.356 (2) | H1···H9iii | 2.942 |
C1···C3 | 2.587 (2) | H2···O1 | 3.44 (2) |
C1···C4 | 3.212 (2) | H2···O1viii | 2.20 (2) |
C1···C5 | 3.244 (2) | H2···O2ix | 2.83 (2) |
C1···C6 | 2.562 (2) | H2···C1 | 3.17 (2) |
C2···O1 | 2.331 (2) | H2···C1viii | 3.15 (2) |
C2···C4 | 2.533 (2) | H2···C2 | 1.93 (2) |
C2···C5 | 3.198 (2) | H2···C3 | 2.51 (2) |
C2···C6 | 3.165 (2) | H2···C3vi | 3.52 (2) |
C2···C7 | 2.553 (2) | H2···C4vi | 3.59 (2) |
C2···C9iii | 3.571 (2) | H2···C7viii | 3.42 (2) |
C3···O1viii | 3.341 (2) | H2···C8ix | 3.59 (2) |
C3···N1 | 2.350 (2) | H2···C9ix | 3.58 (2) |
C3···C1 | 2.587 (2) | H2···H1 | 1.52 (3) |
C3···C5 | 2.516 (2) | H2···H3 | 2.278 |
C3···C6 | 3.101 (2) | H2···H6x | 3.298 |
C3···C7 | 3.108 (2) | H2···H6viii | 2.871 |
C4···O2 | 2.792 (2) | H2···H7ix | 3.077 |
C4···O3 | 3.588 (2) | H2···H9iii | 3.066 |
C4···C1 | 3.212 (2) | H2···H9ix | 3.338 |
C4···C2 | 2.533 (2) | H3···O1viii | 2.509 |
C4···C6 | 2.480 (2) | H3···N1 | 2.456 |
C4···C7 | 3.100 (2) | H3···C1 | 3.384 |
C4···C8 | 2.427 (2) | H3···C1viii | 3.310 |
C5···O2 | 2.391 (2) | H3···C2 | 1.990 |
C5···O3 | 2.366 (2) | H3···C4 | 1.981 |
C5···C1 | 3.244 (2) | H3···C5 | 3.295 |
C5···C2 | 3.198 (2) | H3···C5vi | 3.367 |
C5···C3 | 2.516 (2) | H3···C8vi | 3.476 |
C5···C6i | 3.523 (2) | H3···C9v | 3.127 |
C5···C7 | 2.520 (2) | H3···H1 | 3.347 |
C5···C7i | 3.486 (2) | H3···H1xiv | 3.529 |
C6···O2xi | 3.146 (2) | H3···H2 | 2.278 |
C6···O3 | 2.727 (2) | H3···H4 | 2.183 |
C6···C1 | 2.562 (2) | H3···H6viii | 3.370 |
C6···C2 | 3.165 (2) | H3···H7v | 2.877 |
C6···C3 | 3.101 (2) | H3···H8v | 2.577 |
C6···C4 | 2.480 (2) | H4···O2 | 2.402 |
C6···C5i | 3.523 (2) | H4···O3vi | 3.278 |
C6···C6i | 3.313 (2) | H4···O3v | 2.882 |
C6···C8 | 2.492 (2) | H4···C2 | 3.313 |
C7···O1 | 2.335 (2) | H4···C2xiv | 3.549 |
C7···O2xi | 3.334 (2) | H4···C3 | 1.984 |
C7···N1xii | 3.592 (2) | H4···C5 | 1.982 |
C7···C2 | 2.553 (2) | H4···C6 | 3.283 |
C7···C3 | 3.108 (2) | H4···C8 | 2.467 |
C7···C4 | 3.100 (2) | H4···C8vi | 3.536 |
C7···C5 | 2.520 (2) | H4···C9vi | 3.289 |
C7···C5i | 3.486 (2) | H4···C9v | 3.190 |
C7···C8i | 3.361 (2) | H4···H3 | 2.183 |
C8···C4 | 2.427 (2) | H4···H5v | 2.995 |
C8···C6 | 2.492 (2) | H4···H7v | 3.203 |
C8···C7i | 3.361 (2) | H4···H8vi | 3.140 |
C8···C9 | 2.357 (2) | H4···H8v | 2.928 |
C9···O1xiii | 3.494 (2) | H4···H9vi | 2.964 |
C9···O1i | 3.368 (2) | H5···O2xi | 2.368 |
C9···O2 | 2.621 (2) | H5···O3 | 2.314 |
C9···O2xiv | 3.531 (2) | H5···C1 | 3.338 |
C9···O3vii | 3.325 (2) | H5···C4 | 3.279 |
C9···N1xiii | 3.343 (2) | H5···C5 | 1.998 |
C9···C2xiii | 3.571 (2) | H5···C5i | 3.512 |
C9···C8 | 2.357 (2) | H5···C6i | 3.467 |
O1···H1 | 2.18 (2) | H5···C7 | 1.973 |
O1···H2 | 3.44 (2) | H5···C8 | 2.566 |
O1···H2ii | 2.20 (2) | H5···C8xi | 3.402 |
O1···H3ii | 2.509 | H5···C9vii | 3.486 |
O1···H6 | 2.465 | H5···H1xii | 2.949 |
O1···H7iii | 3.085 | H5···H4xi | 2.995 |
O1···H7i | 2.546 | H5···H6 | 2.158 |
O1···H8iii | 3.090 | H5···H8vii | 2.655 |
O2···H1iv | 2.89 (2) | H5···H9vii | 3.501 |
O2···H2iv | 2.83 (2) | H6···O1 | 2.465 |
O2···H4 | 2.402 | H6···O2i | 3.188 |
O2···H5v | 2.368 | H6···O2xi | 2.733 |
O2···H6i | 3.188 | H6···N1xii | 3.202 |
O2···H6v | 2.733 | H6···N1ii | 3.362 |
O2···H7 | 2.949 | H6···C1 | 2.005 |
O2···H8 | 3.509 | H6···C2 | 3.360 |
O2···H8vi | 3.269 | H6···C5 | 3.296 |
O2···H9 | 2.269 | H6···C5i | 3.429 |
O2···H9vi | 2.900 | H6···C6 | 1.961 |
O3···H4xiv | 3.278 | H6···C8i | 3.207 |
O3···H4xi | 2.882 | H6···C9xi | 3.389 |
O3···H5 | 2.314 | H6···H1xii | 2.512 |
O3···H7 | 2.002 | H6···H2xii | 3.298 |
O3···H8 | 2.002 | H6···H2ii | 2.871 |
O3···H8vii | 2.567 | H6···H3ii | 3.370 |
O3···H9 | 2.002 | H6···H5 | 2.158 |
N1···H3 | 2.456 | H6···H9xi | 2.437 |
N1···H6x | 3.202 | H7···O1xiii | 3.085 |
N1···H6viii | 3.362 | H7···O1i | 2.546 |
N1···H7iii | 3.268 | H7···O2 | 2.949 |
N1···H8iii | 3.267 | H7···O3 | 2.002 |
N1···H9iii | 2.943 | H7···N1xiii | 3.268 |
C1···H1 | 2.42 (2) | H7···C1xiii | 2.970 |
C1···H1xii | 3.57 (2) | H7···C1i | 3.111 |
C1···H2 | 3.17 (2) | H7···C2xiii | 3.122 |
C1···H2ii | 3.15 (2) | H7···C7xiii | 3.564 |
C1···H3 | 3.384 | H7···C8 | 2.800 |
C1···H3ii | 3.310 | H7···H1xiii | 3.227 |
C1···H5 | 3.338 | H7···H1i | 3.257 |
C1···H6 | 2.005 | H7···H2iv | 3.077 |
C1···H7iii | 2.970 | H7···H3xi | 2.877 |
C1···H7i | 3.111 | H7···H4xi | 3.203 |
C1···H8iii | 3.534 | H7···H8 | 1.600 |
C2···H1 | 1.93 (2) | H7···H9 | 1.600 |
C2···H2 | 1.93 (2) | H8···O1xiii | 3.090 |
C2···H3 | 1.990 | H8···O2 | 3.509 |
C2···H4 | 3.313 | H8···O2xiv | 3.269 |
C2···H4vi | 3.549 | H8···O3 | 2.002 |
C2···H6 | 3.360 | H8···O3vii | 2.567 |
C2···H7iii | 3.122 | H8···N1xiii | 3.267 |
C2···H9iii | 3.354 | H8···C1xiii | 3.534 |
C3···H1 | 3.16 (2) | H8···C3xi | 3.352 |
C3···H2 | 2.51 (2) | H8···C4xi | 3.533 |
C3···H2xiv | 3.52 (2) | H8···C5vii | 3.419 |
C3···H4 | 1.984 | H8···C6vii | 3.120 |
C3···H8v | 3.352 | H8···C8 | 3.127 |
C4···H2xiv | 3.59 (2) | H8···C8vii | 3.332 |
C4···H3 | 1.981 | H8···C9vii | 3.403 |
C4···H5 | 3.279 | H8···H1xiii | 2.848 |
C4···H8v | 3.533 | H8···H3xi | 2.577 |
C4···H9vi | 3.440 | H8···H4xiv | 3.140 |
C5···H3 | 3.295 | H8···H4xi | 2.928 |
C5···H3xiv | 3.367 | H8···H5vii | 2.655 |
C5···H4 | 1.982 | H8···H7 | 1.600 |
C5···H5 | 1.998 | H8···H8vii | 3.159 |
C5···H5i | 3.512 | H8···H9 | 1.600 |
C5···H6 | 3.296 | H9···O2 | 2.269 |
C5···H6i | 3.429 | H9···O2xiv | 2.900 |
C5···H8vii | 3.419 | H9···O3 | 2.002 |
C6···H1xii | 3.04 (2) | H9···N1xiii | 2.943 |
C6···H4 | 3.283 | H9···C2xiii | 3.354 |
C6···H5i | 3.467 | H9···C4xiv | 3.440 |
C6···H6 | 1.961 | H9···C7v | 3.358 |
C6···H8vii | 3.120 | H9···C8 | 2.424 |
C7···H1xii | 2.77 (2) | H9···C8xiv | 3.581 |
C7···H2ii | 3.42 (2) | H9···H1xiii | 2.942 |
C7···H5 | 1.973 | H9···H2xiii | 3.066 |
C7···H7iii | 3.564 | H9···H2iv | 3.338 |
C7···H9xi | 3.358 | H9···H4xiv | 2.964 |
C8···H2iv | 3.59 (2) | H9···H5vii | 3.501 |
C8···H3xiv | 3.476 | H9···H6v | 2.437 |
C8···H4 | 2.467 | H9···H7 | 1.600 |
C8···H4xiv | 3.536 | H9···H8 | 1.600 |
C8···H5 | 2.566 | | |
| | | |
C8—O3—C9 | 114.94 (13) | C2—N1—H1 | 118.8 (15) |
O1—C1—C2 | 116.21 (14) | C2—N1—H2 | 121.8 (14) |
O1—C1—C7 | 121.16 (15) | H1—N1—H2 | 119 (2) |
C2—C1—C7 | 122.60 (14) | C2—C3—H3 | 114.6 |
N1—C2—C1 | 113.49 (15) | C4—C3—H3 | 114.6 |
N1—C2—C3 | 119.05 (16) | C3—C4—H4 | 114.9 |
C1—C2—C3 | 127.45 (15) | C5—C4—H4 | 114.9 |
C2—C3—C4 | 130.86 (16) | C5—C6—H5 | 114.9 |
C3—C4—C5 | 130.28 (16) | C7—C6—H5 | 114.9 |
C4—C5—C6 | 125.65 (15) | C1—C7—H6 | 113.7 |
C4—C5—C8 | 115.23 (15) | C6—C7—H6 | 113.8 |
C6—C5—C8 | 119.11 (14) | O3—C9—H7 | 109.5 |
C5—C6—C7 | 130.26 (15) | O3—C9—H8 | 109.5 |
C1—C7—C6 | 132.50 (16) | O3—C9—H9 | 109.5 |
O2—C8—O3 | 122.38 (15) | H7—C9—H8 | 109.5 |
O2—C8—C5 | 124.41 (15) | H7—C9—H9 | 109.5 |
O3—C8—C5 | 113.21 (14) | H8—C9—H9 | 109.5 |
| | | |
C9—O3—C8—O2 | 1.2 (2) | C2—C3—C4—C5 | −3.5 (3) |
C9—O3—C8—C5 | −178.79 (13) | C3—C4—C5—C6 | 0.8 (3) |
O1—C1—C2—N1 | 4.0 (2) | C3—C4—C5—C8 | 179.21 (17) |
O1—C1—C2—C3 | −175.20 (16) | C4—C5—C6—C7 | 3.8 (2) |
O1—C1—C7—C6 | 176.82 (17) | C4—C5—C8—O2 | −16.4 (2) |
C2—C1—C7—C6 | −5.4 (2) | C4—C5—C8—O3 | 163.55 (14) |
C7—C1—C2—N1 | −173.91 (15) | C6—C5—C8—O2 | 162.11 (16) |
C7—C1—C2—C3 | 6.9 (2) | C6—C5—C8—O3 | −17.9 (2) |
N1—C2—C3—C4 | 179.37 (18) | C8—C5—C6—C7 | −174.55 (16) |
C1—C2—C3—C4 | −1.5 (3) | C5—C6—C7—C1 | −1.4 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1/2, −y, z−1/2; (v) x−1/2, −y+1/2, −z+1; (vi) −x+1/2, y−1/2, z; (vii) −x+1, −y+1, −z+1; (viii) x−1/2, y, −z+3/2; (ix) −x+1/2, −y, z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) x+1/2, −y+1/2, −z+1; (xii) −x+1, y+1/2, −z+3/2; (xiii) x, −y+1/2, z−1/2; (xiv) −x+1/2, y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.90 (2) | 2.18 (2) | 2.574 (2) | 106 (2) |
N1—H2···O1viii | 0.87 (2) | 2.20 (2) | 3.029 (2) | 159 (2) |
N1—H1···C7x | 0.87 (2) | 2.77 (2) | 3.592 (2) | 153 (2) |
C3—H3···O1viii | 0.95 | 2.51 | 3.341 (2) | 146 |
C6—H5···O2xi | 0.95 | 2.37 | 3.146 (2) | 139 |
C9—H7···O1i | 0.98 | 2.55 | 3.368 (2) | 142 |
C9—H8···O3vii | 0.98 | 2.57 | 3.325 (2) | 134 |
Symmetry codes: (i) −x+1, −y, −z+1; (vii) −x+1, −y+1, −z+1; (viii) x−1/2, y, −z+3/2; (x) −x+1, y−1/2, −z+3/2; (xi) x+1/2, −y+1/2, −z+1. |
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