Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110005732/ps5004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110005732/ps5004Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110005732/ps5004IIsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110005732/ps5004sup4.pdf |
CCDC references: 775213; 775214
For both structures, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C4H9NO2 | F(000) = 448 |
Mr = 103.12 | Dx = 1.296 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2696 reflections |
a = 9.614 (6) Å | θ = 2.5–27.8° |
b = 5.227 (3) Å | µ = 0.10 mm−1 |
c = 21.385 (13) Å | T = 110 K |
β = 100.326 (7)° | Elongated plate, colourless |
V = 1057.1 (11) Å3 | 1.10 × 0.34 × 0.10 mm |
Z = 8 |
Bruker Apex II CCD diffractometer | 2700 independent reflections |
Radiation source: fine-focus sealed tube | 2468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 8.3 pixels mm-1 | θmax = 28.6°, θmin = 2.2° |
Sets of exposures each taken over 0.5° ω rotation scans | h = −12→12 |
Absorption correction: multi-scan SADABS (Bruker, 2007) | k = −7→6 |
Tmin = 0.749, Tmax = 0.990 | l = −28→26 |
6460 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.085P)2 + 0.488P] where P = (Fo2 + 2Fc2)/3 |
2700 reflections | (Δ/σ)max < 0.001 |
261 parameters | Δρmax = 0.37 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
0 constraints |
Experimental. Soft crystal, easily bent. |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.1618 (2) | 0.7249 (5) | 0.05862 (11) | 0.0189 (5) | |
O2A | 0.2490 (3) | 0.3333 (5) | 0.08128 (13) | 0.0269 (6) | |
N1A | 0.4156 (3) | 0.9310 (5) | 0.05725 (12) | 0.0165 (6) | |
H1A | 0.3903 | 0.9014 | 0.0148 | 0.025* | |
H2A | 0.5047 | 0.9968 | 0.0655 | 0.025* | |
H3A | 0.3543 | 1.0444 | 0.0698 | 0.025* | |
C1A | 0.2622 (3) | 0.5696 (7) | 0.07523 (15) | 0.0162 (6) | |
C2A | 0.4119 (3) | 0.6861 (7) | 0.09261 (16) | 0.0185 (7) | |
H21A | 0.4815 | 0.5645 | 0.0794 | 0.022* | |
C3A | 0.4532 (4) | 0.7370 (9) | 0.16363 (16) | 0.0291 (8) | |
H31A | 0.3766 | 0.8344 | 0.1781 | 0.035* | |
H32A | 0.5395 | 0.8443 | 0.1713 | 0.035* | |
C4A | 0.4810 (4) | 0.4918 (11) | 0.20304 (18) | 0.0413 (11) | |
H41A | 0.5037 | 0.5357 | 0.2483 | 0.062* | |
H42A | 0.5607 | 0.3993 | 0.1908 | 0.062* | |
H43A | 0.3965 | 0.3833 | 0.1953 | 0.062* | |
O1B | 0.6611 (2) | 0.2229 (5) | 0.06230 (11) | 0.0197 (5) | |
O2B | 0.7617 (3) | −0.1383 (5) | 0.10293 (13) | 0.0266 (6) | |
N1B | 0.9102 (3) | 0.4579 (6) | 0.06143 (12) | 0.0150 (5) | |
H1B | 0.8819 | 0.4100 | 0.0202 | 0.023* | |
H2B | 0.9993 | 0.5231 | 0.0667 | 0.023* | |
H3B | 0.8502 | 0.5791 | 0.0717 | 0.023* | |
C1B | 0.7664 (3) | 0.0909 (7) | 0.08684 (14) | 0.0164 (6) | |
C2B | 0.9089 (3) | 0.2305 (7) | 0.10364 (16) | 0.0206 (7) | |
H21B | 0.9874 | 0.1115 | 0.0983 | 0.025* | |
C3B | 0.9265 (4) | 0.3171 (8) | 0.17455 (16) | 0.0277 (8) | |
H31B | 0.8420 | 0.4167 | 0.1801 | 0.033* | |
H32B | 0.9304 | 0.1630 | 0.2017 | 0.033* | |
C4B | 1.0564 (4) | 0.4770 (10) | 0.19724 (17) | 0.0330 (9) | |
H41B | 1.0695 | 0.4971 | 0.2435 | 0.050* | |
H42B | 1.0447 | 0.6458 | 0.1770 | 0.050* | |
H43B | 1.1394 | 0.3921 | 0.1860 | 0.050* | |
O1C | 0.1142 (2) | 0.1140 (5) | 0.43818 (10) | 0.0187 (5) | |
O2C | 0.1771 (2) | 0.4896 (5) | 0.40269 (13) | 0.0262 (6) | |
N1C | 0.3644 (3) | −0.1063 (6) | 0.44032 (12) | 0.0165 (5) | |
H1C | 0.4488 | −0.1724 | 0.4347 | 0.025* | |
H2C | 0.2934 | −0.2140 | 0.4231 | 0.025* | |
H3C | 0.3643 | −0.0877 | 0.4826 | 0.025* | |
C1C | 0.2007 (3) | 0.2611 (7) | 0.41789 (15) | 0.0176 (6) | |
C2C | 0.3426 (3) | 0.1488 (6) | 0.40840 (15) | 0.0174 (6) | |
H21C | 0.4195 | 0.2660 | 0.4290 | 0.021* | |
C3C | 0.3509 (4) | 0.1284 (8) | 0.33786 (16) | 0.0264 (8) | |
H31C | 0.3459 | 0.3027 | 0.3195 | 0.032* | |
H32C | 0.4439 | 0.0551 | 0.3338 | 0.032* | |
C4C | 0.2358 (4) | −0.0335 (10) | 0.29949 (16) | 0.0349 (9) | |
H41C | 0.2479 | −0.0364 | 0.2550 | 0.052* | |
H42C | 0.1432 | 0.0393 | 0.3023 | 0.052* | |
H43C | 0.2418 | −0.2083 | 0.3163 | 0.052* | |
O1D | 0.6104 (2) | 0.6060 (5) | 0.43697 (10) | 0.0189 (5) | |
O2D | 0.6838 (2) | 1.0001 (5) | 0.41945 (13) | 0.0272 (6) | |
N1D | 0.8699 (3) | 0.4063 (5) | 0.44150 (12) | 0.0161 (6) | |
H1D | 0.9521 | 0.3410 | 0.4327 | 0.024* | |
H2D | 0.7987 | 0.2920 | 0.4296 | 0.024* | |
H3D | 0.8797 | 0.4370 | 0.4840 | 0.024* | |
C1D | 0.6999 (3) | 0.7623 (7) | 0.42291 (15) | 0.0168 (6) | |
C2D | 0.8361 (3) | 0.6502 (6) | 0.40584 (15) | 0.0161 (6) | |
H21D | 0.9153 | 0.7740 | 0.4187 | 0.019* | |
C3D | 0.8199 (3) | 0.5966 (7) | 0.33422 (15) | 0.0223 (7) | |
H31D | 0.9062 | 0.5093 | 0.3259 | 0.027* | |
H32D | 0.7391 | 0.4791 | 0.3213 | 0.027* | |
C4D | 0.7962 (4) | 0.8363 (9) | 0.29379 (17) | 0.0303 (8) | |
H41D | 0.7890 | 0.7903 | 0.2489 | 0.045* | |
H42D | 0.8759 | 0.9538 | 0.3062 | 0.045* | |
H43D | 0.7086 | 0.9197 | 0.3002 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0137 (9) | 0.0180 (12) | 0.0248 (12) | −0.0022 (9) | 0.0029 (8) | 0.0034 (10) |
O2A | 0.0188 (11) | 0.0160 (13) | 0.0468 (15) | −0.0007 (10) | 0.0087 (10) | 0.0047 (12) |
N1A | 0.0134 (11) | 0.0143 (15) | 0.0220 (13) | −0.0010 (10) | 0.0040 (9) | 0.0002 (10) |
C1A | 0.0145 (13) | 0.0158 (16) | 0.0185 (14) | −0.0019 (12) | 0.0035 (10) | 0.0007 (12) |
C2A | 0.0124 (13) | 0.0163 (17) | 0.0274 (16) | 0.0005 (12) | 0.0051 (11) | 0.0024 (12) |
C3A | 0.0209 (15) | 0.040 (2) | 0.0262 (18) | −0.0064 (16) | 0.0030 (12) | 0.0036 (17) |
C4A | 0.0315 (19) | 0.060 (3) | 0.0280 (19) | −0.010 (2) | −0.0059 (14) | 0.016 (2) |
O1B | 0.0133 (9) | 0.0218 (13) | 0.0242 (11) | −0.0031 (10) | 0.0039 (8) | 0.0027 (10) |
O2B | 0.0217 (12) | 0.0130 (12) | 0.0470 (15) | −0.0015 (10) | 0.0114 (10) | 0.0025 (12) |
N1B | 0.0122 (10) | 0.0121 (13) | 0.0209 (13) | −0.0026 (10) | 0.0034 (8) | 0.0001 (10) |
C1B | 0.0179 (14) | 0.0147 (16) | 0.0177 (14) | −0.0016 (13) | 0.0062 (10) | −0.0024 (13) |
C2B | 0.0125 (13) | 0.0176 (17) | 0.0305 (17) | −0.0013 (12) | 0.0009 (11) | 0.0073 (14) |
C3B | 0.0239 (16) | 0.031 (2) | 0.0277 (18) | −0.0062 (15) | 0.0028 (12) | 0.0050 (15) |
C4B | 0.0252 (17) | 0.044 (2) | 0.0295 (18) | −0.0087 (18) | 0.0028 (13) | −0.0009 (18) |
O1C | 0.0149 (10) | 0.0183 (12) | 0.0238 (11) | 0.0038 (9) | 0.0060 (8) | 0.0029 (10) |
O2C | 0.0178 (11) | 0.0156 (13) | 0.0451 (15) | 0.0027 (10) | 0.0050 (9) | 0.0034 (12) |
N1C | 0.0129 (11) | 0.0148 (14) | 0.0224 (13) | 0.0019 (10) | 0.0048 (9) | 0.0006 (11) |
C1C | 0.0161 (13) | 0.0157 (17) | 0.0203 (15) | 0.0005 (13) | 0.0014 (10) | −0.0018 (13) |
C2C | 0.0149 (13) | 0.0115 (15) | 0.0258 (16) | 0.0021 (12) | 0.0037 (11) | 0.0018 (12) |
C3C | 0.0230 (15) | 0.029 (2) | 0.0286 (18) | 0.0039 (15) | 0.0091 (12) | 0.0038 (16) |
C4C | 0.045 (2) | 0.038 (2) | 0.0219 (18) | 0.000 (2) | 0.0056 (14) | 0.0015 (17) |
O1D | 0.0143 (10) | 0.0153 (12) | 0.0277 (12) | 0.0011 (9) | 0.0057 (8) | 0.0013 (10) |
O2D | 0.0156 (11) | 0.0154 (13) | 0.0516 (16) | 0.0040 (10) | 0.0083 (10) | 0.0028 (12) |
N1D | 0.0113 (11) | 0.0150 (14) | 0.0223 (13) | 0.0025 (10) | 0.0039 (9) | −0.0006 (10) |
C1D | 0.0137 (13) | 0.0152 (16) | 0.0214 (15) | 0.0015 (12) | 0.0029 (10) | −0.0011 (13) |
C2D | 0.0127 (13) | 0.0133 (15) | 0.0229 (16) | 0.0009 (11) | 0.0045 (10) | 0.0019 (12) |
C3D | 0.0203 (15) | 0.0232 (18) | 0.0237 (16) | 0.0008 (14) | 0.0045 (11) | −0.0013 (14) |
C4D | 0.0333 (19) | 0.031 (2) | 0.0276 (18) | −0.0018 (16) | 0.0071 (14) | 0.0037 (16) |
O1A—C1A | 1.262 (4) | O1C—C1C | 1.265 (4) |
O2A—C1A | 1.251 (4) | O2C—C1C | 1.248 (5) |
N1A—C2A | 1.490 (4) | N1C—C2C | 1.495 (4) |
N1A—H1A | 0.9100 | N1C—H1C | 0.9100 |
N1A—H2A | 0.9100 | N1C—H2C | 0.9100 |
N1A—H3A | 0.9100 | N1C—H3C | 0.9100 |
C1A—C2A | 1.545 (4) | C1C—C2C | 1.532 (4) |
C2A—C3A | 1.523 (5) | C2C—C3C | 1.529 (5) |
C2A—H21A | 1.0000 | C2C—H21C | 1.0000 |
C3A—C4A | 1.531 (5) | C3C—C4C | 1.513 (5) |
C3A—H31A | 0.9900 | C3C—H31C | 0.9900 |
C3A—H32A | 0.9900 | C3C—H32C | 0.9900 |
C4A—H41A | 0.9800 | C4C—H41C | 0.9800 |
C4A—H42A | 0.9800 | C4C—H42C | 0.9800 |
C4A—H43A | 0.9800 | C4C—H43C | 0.9800 |
O1B—C1B | 1.259 (4) | O1D—C1D | 1.261 (4) |
O2B—C1B | 1.249 (4) | O2D—C1D | 1.253 (4) |
N1B—C2B | 1.494 (4) | N1D—C2D | 1.491 (4) |
N1B—H1B | 0.9100 | N1D—H1D | 0.9100 |
N1B—H2B | 0.9100 | N1D—H2D | 0.9100 |
N1B—H3B | 0.9100 | N1D—H3D | 0.9100 |
C1B—C2B | 1.537 (4) | C1D—C2D | 1.536 (4) |
C2B—C3B | 1.562 (5) | C2D—C3D | 1.537 (4) |
C2B—H21B | 1.0000 | C2D—H21D | 1.0000 |
C3B—C4B | 1.509 (5) | C3D—C4D | 1.516 (5) |
C3B—H31B | 0.9900 | C3D—H31D | 0.9900 |
C3B—H32B | 0.9900 | C3D—H32D | 0.9900 |
C4B—H41B | 0.9800 | C4D—H41D | 0.9800 |
C4B—H42B | 0.9800 | C4D—H42D | 0.9800 |
C4B—H43B | 0.9800 | C4D—H43D | 0.9800 |
C2A—N1A—H1A | 109.5 | C2C—N1C—H1C | 109.5 |
C2A—N1A—H2A | 109.5 | C2C—N1C—H2C | 109.5 |
H1A—N1A—H2A | 109.5 | H1C—N1C—H2C | 109.5 |
C2A—N1A—H3A | 109.5 | C2C—N1C—H3C | 109.5 |
H1A—N1A—H3A | 109.5 | H1C—N1C—H3C | 109.5 |
H2A—N1A—H3A | 109.5 | H2C—N1C—H3C | 109.5 |
O2A—C1A—O1A | 125.2 (3) | O2C—C1C—O1C | 124.8 (3) |
O2A—C1A—C2A | 118.2 (3) | O2C—C1C—C2C | 117.2 (3) |
O1A—C1A—C2A | 116.5 (3) | O1C—C1C—C2C | 117.9 (3) |
N1A—C2A—C3A | 109.3 (3) | N1C—C2C—C3C | 111.1 (3) |
N1A—C2A—C1A | 108.8 (2) | N1C—C2C—C1C | 109.7 (2) |
C3A—C2A—C1A | 112.0 (3) | C3C—C2C—C1C | 111.3 (3) |
N1A—C2A—H21A | 108.9 | N1C—C2C—H21C | 108.2 |
C3A—C2A—H21A | 108.9 | C3C—C2C—H21C | 108.2 |
C1A—C2A—H21A | 108.9 | C1C—C2C—H21C | 108.2 |
C2A—C3A—C4A | 113.1 (3) | C4C—C3C—C2C | 114.3 (3) |
C2A—C3A—H31A | 109.0 | C4C—C3C—H31C | 108.7 |
C4A—C3A—H31A | 109.0 | C2C—C3C—H31C | 108.7 |
C2A—C3A—H32A | 109.0 | C4C—C3C—H32C | 108.7 |
C4A—C3A—H32A | 109.0 | C2C—C3C—H32C | 108.7 |
H31A—C3A—H32A | 107.8 | H31C—C3C—H32C | 107.6 |
C3A—C4A—H41A | 109.5 | C3C—C4C—H41C | 109.5 |
C3A—C4A—H42A | 109.5 | C3C—C4C—H42C | 109.5 |
H41A—C4A—H42A | 109.5 | H41C—C4C—H42C | 109.5 |
C3A—C4A—H43A | 109.5 | C3C—C4C—H43C | 109.5 |
H41A—C4A—H43A | 109.5 | H41C—C4C—H43C | 109.5 |
H42A—C4A—H43A | 109.5 | H42C—C4C—H43C | 109.5 |
C2B—N1B—H1B | 109.5 | C2D—N1D—H1D | 109.5 |
C2B—N1B—H2B | 109.5 | C2D—N1D—H2D | 109.5 |
H1B—N1B—H2B | 109.5 | H1D—N1D—H2D | 109.5 |
C2B—N1B—H3B | 109.5 | C2D—N1D—H3D | 109.5 |
H1B—N1B—H3B | 109.5 | H1D—N1D—H3D | 109.5 |
H2B—N1B—H3B | 109.5 | H2D—N1D—H3D | 109.5 |
O2B—C1B—O1B | 125.1 (3) | O2D—C1D—O1D | 125.0 (3) |
O2B—C1B—C2B | 117.7 (3) | O2D—C1D—C2D | 117.8 (3) |
O1B—C1B—C2B | 117.0 (3) | O1D—C1D—C2D | 117.1 (3) |
N1B—C2B—C1B | 109.9 (2) | N1D—C2D—C1D | 108.8 (2) |
N1B—C2B—C3B | 110.2 (3) | N1D—C2D—C3D | 109.1 (3) |
C1B—C2B—C3B | 107.6 (3) | C1D—C2D—C3D | 111.6 (2) |
N1B—C2B—H21B | 109.7 | N1D—C2D—H21D | 109.1 |
C1B—C2B—H21B | 109.7 | C1D—C2D—H21D | 109.1 |
C3B—C2B—H21B | 109.7 | C3D—C2D—H21D | 109.1 |
C4B—C3B—C2B | 114.4 (3) | C4D—C3D—C2D | 113.3 (3) |
C4B—C3B—H31B | 108.7 | C4D—C3D—H31D | 108.9 |
C2B—C3B—H31B | 108.7 | C2D—C3D—H31D | 108.9 |
C4B—C3B—H32B | 108.7 | C4D—C3D—H32D | 108.9 |
C2B—C3B—H32B | 108.7 | C2D—C3D—H32D | 108.9 |
H31B—C3B—H32B | 107.6 | H31D—C3D—H32D | 107.7 |
C3B—C4B—H41B | 109.5 | C3D—C4D—H41D | 109.5 |
C3B—C4B—H42B | 109.5 | C3D—C4D—H42D | 109.5 |
H41B—C4B—H42B | 109.5 | H41D—C4D—H42D | 109.5 |
C3B—C4B—H43B | 109.5 | C3D—C4D—H43D | 109.5 |
H41B—C4B—H43B | 109.5 | H41D—C4D—H43D | 109.5 |
H42B—C4B—H43B | 109.5 | H42D—C4D—H43D | 109.5 |
N1A—C2A—C1A—O1A | −27.4 (4) | O2B—C1B—C2B—N1B | 158.7 (3) |
N1A—C2A—C3A—C4A | −168.6 (3) | O2B—C1B—C2B—C3B | −81.4 (4) |
N1B—C2B—C1B—O1B | −26.7 (4) | O1B—C1B—C2B—C3B | 93.2 (3) |
N1B—C2B—C3B—C4B | −55.5 (4) | C1B—C2B—C3B—C4B | −175.2 (3) |
N1C—C2C—C1C—O1C | −13.5 (4) | O2C—C1C—C2C—N1C | 169.1 (3) |
N1C—C2C—C3C—C4C | 64.2 (4) | O2C—C1C—C2C—C3C | −67.5 (4) |
N1D—C2D—C1D—O1D | −30.4 (4) | O1C—C1C—C2C—C3C | 109.9 (3) |
N1D—C2D—C3D—C4D | −175.6 (3) | C1C—C2C—C3C—C4C | −58.4 (4) |
O2A—C1A—C2A—N1A | 155.7 (3) | O2D—C1D—C2D—N1D | 152.3 (3) |
O2A—C1A—C2A—C3A | −83.4 (4) | O2D—C1D—C2D—C3D | −87.3 (4) |
O1A—C1A—C2A—C3A | 93.5 (4) | O1D—C1D—C2D—C3D | 90.0 (4) |
C1A—C2A—C3A—C4A | 70.8 (4) | C1D—C2D—C3D—C4D | 64.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1Bi | 0.91 | 1.88 | 2.754 (4) | 160 |
N1A—H2A···O1Bii | 0.91 | 1.92 | 2.796 (4) | 160 |
N1A—H3A···O2Aii | 0.91 | 1.86 | 2.747 (4) | 165 |
N1B—H1B···O1Aiii | 0.91 | 1.92 | 2.814 (4) | 165 |
N1B—H2B···O1Aiv | 0.91 | 1.92 | 2.803 (3) | 164 |
N1B—H3B···O2Bii | 0.91 | 1.89 | 2.781 (4) | 168 |
N1C—H1C···O1Dv | 0.91 | 1.93 | 2.815 (4) | 163 |
N1C—H2C···O2Cv | 0.91 | 1.91 | 2.799 (4) | 163 |
N1C—H3C···O1Dvi | 0.91 | 1.97 | 2.819 (4) | 154 |
N1D—H1D···O1Civ | 0.91 | 1.95 | 2.813 (3) | 159 |
N1D—H2D···O2Dv | 0.91 | 1.87 | 2.762 (4) | 165 |
N1D—H3D···O1Cvii | 0.91 | 1.90 | 2.771 (4) | 161 |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z; (iv) x+1, y, z; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+1; (vii) −x+1, y+1/2, −z+1. |
C4H9NO2 | F(000) = 896 |
Mr = 103.12 | Dx = 1.291 Mg m−3 |
Monoclinic, I2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: I 2y | Cell parameters from 3867 reflections |
a = 9.646 (2) Å | θ = 1.9–25.0° |
b = 5.2145 (12) Å | µ = 0.10 mm−1 |
c = 42.885 (10) Å | T = 110 K |
β = 100.295 (3)° | Block, colourless |
V = 2122.5 (8) Å3 | 0.40 × 0.32 × 0.18 mm |
Z = 16 |
Bruker Apex II CCD diffractometer | 2083 independent reflections |
Radiation source: fine-focus sealed tube | 1852 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.3 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
Sets of exposures each taken over 0.5° ω rotation scans | h = −11→11 |
Absorption correction: multi-scan SADABS (Bruker, 2007) | k = −6→6 |
Tmin = 0.791, Tmax = 0.982 | l = −50→50 |
7238 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0531P)2 + 3.6316P] where P = (Fo2 + 2Fc2)/3 |
2083 reflections | (Δ/σ)max < 0.001 |
261 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
0 constraints |
Experimental. Broad reflections |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | −0.0869 (2) | 0.7794 (5) | 0.03248 (6) | 0.0173 (6) | |
O2A | 0.0039 (3) | 0.3905 (5) | 0.04313 (7) | 0.0235 (7) | |
N1A | 0.1646 (3) | 0.9851 (6) | 0.02779 (6) | 0.0147 (7) | |
H1A | 0.1327 | 0.9516 | 0.0069 | 0.022* | |
H2A | 0.2539 | 1.0481 | 0.0303 | 0.022* | |
H3A | 0.1075 | 1.1029 | 0.0347 | 0.022* | |
C1A | 0.0151 (4) | 0.6258 (8) | 0.03974 (8) | 0.0157 (8) | |
C2A | 0.1642 (3) | 0.7444 (7) | 0.04644 (8) | 0.0160 (8) | |
H21A | 0.2329 | 0.6204 | 0.0400 | 0.019* | |
C3A | 0.2086 (4) | 0.8080 (9) | 0.08173 (8) | 0.0256 (9) | |
H32A | 0.2977 | 0.9066 | 0.0847 | 0.031* | |
H31A | 0.1359 | 0.9192 | 0.0883 | 0.031* | |
C4A | 0.2295 (4) | 0.5748 (11) | 0.10308 (10) | 0.0372 (12) | |
H41A | 0.2625 | 0.6292 | 0.1250 | 0.056* | |
H42A | 0.2996 | 0.4610 | 0.0964 | 0.056* | |
H43A | 0.1399 | 0.4831 | 0.1016 | 0.056* | |
O1B | 0.4092 (2) | 0.2807 (5) | 0.02806 (5) | 0.0171 (6) | |
O2B | 0.5037 (3) | −0.0834 (5) | 0.04897 (7) | 0.0253 (7) | |
N1B | 0.6605 (3) | 0.5128 (7) | 0.03150 (6) | 0.0141 (6) | |
H1B | 0.6329 | 0.4693 | 0.0108 | 0.021* | |
H2B | 0.7505 | 0.5731 | 0.0346 | 0.021* | |
H3B | 0.6024 | 0.6367 | 0.0368 | 0.021* | |
C1B | 0.5113 (3) | 0.1463 (8) | 0.04154 (8) | 0.0146 (8) | |
C2B | 0.6537 (3) | 0.2824 (8) | 0.05180 (8) | 0.0155 (8) | |
H21B | 0.7318 | 0.1621 | 0.0493 | 0.019* | |
C3B | 0.6679 (4) | 0.3597 (8) | 0.08685 (8) | 0.0211 (9) | |
H31B | 0.5844 | 0.4625 | 0.0895 | 0.025* | |
H32B | 0.6677 | 0.2024 | 0.0998 | 0.025* | |
C4B | 0.7997 (4) | 0.5129 (10) | 0.09953 (8) | 0.0275 (9) | |
H41B | 0.8093 | 0.5310 | 0.1226 | 0.041* | |
H42B | 0.7927 | 0.6831 | 0.0897 | 0.041* | |
H43B | 0.8824 | 0.4234 | 0.0945 | 0.041* | |
O1C | −0.1360 (2) | 0.1523 (5) | 0.21886 (5) | 0.0157 (5) | |
O2C | −0.0733 (3) | 0.5268 (5) | 0.20093 (6) | 0.0232 (6) | |
N1C | 0.1143 (3) | −0.0685 (6) | 0.21989 (6) | 0.0151 (7) | |
H1C | 0.1128 | −0.0502 | 0.2409 | 0.023* | |
H3C | 0.1990 | −0.1337 | 0.2173 | 0.023* | |
H2C | 0.0443 | −0.1773 | 0.2111 | 0.023* | |
C1C | −0.0498 (4) | 0.2987 (8) | 0.20865 (8) | 0.0155 (8) | |
C2C | 0.0925 (4) | 0.1868 (7) | 0.20399 (8) | 0.0159 (8) | |
H21C | 0.1690 | 0.3048 | 0.2142 | 0.019* | |
C3C | 0.1008 (4) | 0.1653 (9) | 0.16876 (8) | 0.0218 (9) | |
H31C | 0.0963 | 0.3398 | 0.1596 | 0.026* | |
H32C | 0.1934 | 0.0911 | 0.1668 | 0.026* | |
C4C | −0.0146 (4) | 0.0026 (10) | 0.14943 (8) | 0.0279 (9) | |
H41C | −0.0048 | 0.0061 | 0.1271 | 0.042* | |
H42C | −0.1069 | 0.0715 | 0.1516 | 0.042* | |
H43C | −0.0064 | −0.1745 | 0.1572 | 0.042* | |
O1D | 0.3607 (2) | 0.6429 (5) | 0.21874 (5) | 0.0160 (6) | |
O2D | 0.4339 (3) | 1.0372 (5) | 0.21033 (6) | 0.0238 (6) | |
N1D | 0.6197 (3) | 0.4426 (6) | 0.22100 (6) | 0.0138 (7) | |
H1D | 0.6245 | 0.4710 | 0.2421 | 0.021* | |
H2D | 0.5512 | 0.3250 | 0.2142 | 0.021* | |
H3D | 0.7040 | 0.3824 | 0.2175 | 0.021* | |
C1D | 0.4505 (3) | 0.8002 (8) | 0.21183 (8) | 0.0139 (8) | |
C2D | 0.5857 (3) | 0.6874 (7) | 0.20336 (8) | 0.0141 (8) | |
H21D | 0.6647 | 0.8114 | 0.2098 | 0.017* | |
C3D | 0.5697 (4) | 0.6341 (8) | 0.16771 (8) | 0.0201 (8) | |
H31D | 0.6544 | 0.5416 | 0.1637 | 0.024* | |
H32D | 0.4873 | 0.5210 | 0.1611 | 0.024* | |
C4D | 0.5508 (4) | 0.8772 (9) | 0.14760 (9) | 0.0263 (10) | |
H41D | 0.5433 | 0.8316 | 0.1252 | 0.039* | |
H42D | 0.6321 | 0.9902 | 0.1539 | 0.039* | |
H43D | 0.4648 | 0.9659 | 0.1507 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0135 (11) | 0.0169 (14) | 0.0220 (12) | −0.0016 (12) | 0.0046 (9) | 0.0043 (12) |
O2A | 0.0205 (14) | 0.0143 (17) | 0.0377 (16) | −0.0023 (12) | 0.0105 (12) | 0.0035 (13) |
N1A | 0.0123 (13) | 0.0145 (17) | 0.0183 (14) | −0.0026 (13) | 0.0055 (11) | −0.0029 (14) |
C1A | 0.0146 (17) | 0.019 (2) | 0.0158 (18) | −0.0013 (17) | 0.0080 (14) | 0.0012 (17) |
C2A | 0.0141 (16) | 0.013 (2) | 0.0222 (18) | −0.0016 (16) | 0.0062 (14) | 0.0021 (16) |
C3A | 0.0186 (18) | 0.035 (3) | 0.0237 (19) | −0.005 (2) | 0.0044 (15) | 0.000 (2) |
C4A | 0.028 (2) | 0.052 (3) | 0.029 (2) | −0.008 (2) | −0.0027 (17) | 0.014 (2) |
O1B | 0.0136 (11) | 0.0170 (14) | 0.0209 (13) | −0.0019 (12) | 0.0037 (10) | 0.0020 (12) |
O2B | 0.0198 (13) | 0.0113 (15) | 0.0475 (17) | −0.0005 (12) | 0.0130 (12) | 0.0023 (14) |
N1B | 0.0106 (13) | 0.0127 (16) | 0.0197 (14) | −0.0022 (13) | 0.0046 (11) | 0.0002 (14) |
C1B | 0.0136 (17) | 0.013 (2) | 0.0192 (18) | 0.0010 (17) | 0.0093 (14) | −0.0016 (17) |
C2B | 0.0144 (16) | 0.0090 (19) | 0.0234 (18) | 0.0011 (16) | 0.0041 (14) | 0.0043 (17) |
C3B | 0.0224 (19) | 0.023 (2) | 0.0190 (18) | −0.0029 (17) | 0.0070 (15) | 0.0048 (16) |
C4B | 0.028 (2) | 0.036 (2) | 0.0186 (18) | −0.009 (2) | 0.0039 (15) | −0.003 (2) |
O1C | 0.0131 (11) | 0.0126 (13) | 0.0227 (12) | 0.0020 (11) | 0.0063 (9) | 0.0027 (12) |
O2C | 0.0179 (12) | 0.0123 (14) | 0.0392 (15) | 0.0044 (12) | 0.0048 (11) | 0.0066 (15) |
N1C | 0.0144 (14) | 0.0132 (16) | 0.0188 (15) | 0.0017 (14) | 0.0055 (11) | −0.0003 (13) |
C1C | 0.0156 (16) | 0.015 (2) | 0.0160 (17) | −0.0003 (17) | 0.0019 (13) | −0.0028 (17) |
C2C | 0.0144 (16) | 0.0120 (19) | 0.0218 (18) | −0.0002 (16) | 0.0041 (14) | −0.0012 (16) |
C3C | 0.0191 (17) | 0.023 (2) | 0.026 (2) | 0.0007 (18) | 0.0097 (15) | 0.0028 (19) |
C4C | 0.039 (2) | 0.028 (2) | 0.0178 (18) | 0.000 (2) | 0.0076 (16) | 0.0014 (19) |
O1D | 0.0112 (11) | 0.0133 (14) | 0.0247 (13) | 0.0021 (11) | 0.0065 (9) | 0.0025 (12) |
O2D | 0.0205 (13) | 0.0103 (15) | 0.0419 (16) | 0.0024 (13) | 0.0092 (12) | 0.0020 (14) |
N1D | 0.0122 (14) | 0.0110 (16) | 0.0189 (14) | 0.0014 (13) | 0.0042 (11) | −0.0022 (13) |
C1D | 0.0148 (16) | 0.014 (2) | 0.0120 (16) | 0.0012 (17) | 0.0008 (13) | −0.0008 (16) |
C2D | 0.0146 (16) | 0.0070 (18) | 0.0208 (18) | 0.0021 (15) | 0.0038 (13) | 0.0011 (15) |
C3D | 0.0201 (18) | 0.021 (2) | 0.0208 (18) | 0.0019 (18) | 0.0079 (14) | −0.0001 (18) |
C4D | 0.031 (2) | 0.027 (2) | 0.0226 (19) | −0.0012 (19) | 0.0087 (16) | 0.0057 (18) |
O1A—C1A | 1.264 (5) | O1C—C1C | 1.263 (4) |
O2A—C1A | 1.243 (5) | O2C—C1C | 1.245 (5) |
N1A—C2A | 1.489 (5) | N1C—C2C | 1.494 (5) |
N1A—H1A | 0.9100 | N1C—H1C | 0.9100 |
N1A—H2A | 0.9100 | N1C—H3C | 0.9100 |
N1A—H3A | 0.9100 | N1C—H2C | 0.9100 |
C1A—C2A | 1.544 (5) | C1C—C2C | 1.538 (5) |
C2A—C3A | 1.534 (5) | C2C—C3C | 1.531 (5) |
C2A—H21A | 1.0000 | C2C—H21C | 1.0000 |
C3A—C4A | 1.514 (6) | C3C—C4C | 1.522 (6) |
C3A—H32A | 0.9900 | C3C—H31C | 0.9900 |
C3A—H31A | 0.9900 | C3C—H32C | 0.9900 |
C4A—H41A | 0.9800 | C4C—H41C | 0.9800 |
C4A—H42A | 0.9800 | C4C—H42C | 0.9800 |
C4A—H43A | 0.9800 | C4C—H43C | 0.9800 |
O1B—C1B | 1.261 (4) | O1D—C1D | 1.266 (4) |
O2B—C1B | 1.245 (5) | O2D—C1D | 1.247 (5) |
N1B—C2B | 1.492 (5) | N1D—C2D | 1.490 (5) |
N1B—H1B | 0.9100 | N1D—H3D | 0.9100 |
N1B—H2B | 0.9100 | N1D—H2D | 0.9100 |
N1B—H3B | 0.9100 | N1D—H1D | 0.9100 |
C1B—C2B | 1.539 (5) | C1D—C2D | 1.532 (5) |
C2B—C3B | 1.538 (5) | C2D—C3D | 1.534 (5) |
C2B—H21B | 1.0000 | C2D—H21D | 1.0000 |
C3B—C4B | 1.518 (5) | C3D—C4D | 1.526 (6) |
C3B—H31B | 0.9900 | C3D—H31D | 0.9900 |
C3B—H32B | 0.9900 | C3D—H32D | 0.9900 |
C4B—H41B | 0.9800 | C4D—H41D | 0.9800 |
C4B—H42B | 0.9800 | C4D—H42D | 0.9800 |
C4B—H43B | 0.9800 | C4D—H43D | 0.9800 |
C2A—N1A—H1A | 109.5 | C2C—N1C—H1C | 109.5 |
C2A—N1A—H2A | 109.5 | C2C—N1C—H3C | 109.5 |
H1A—N1A—H2A | 109.5 | H1C—N1C—H3C | 109.5 |
C2A—N1A—H3A | 109.5 | C2C—N1C—H2C | 109.5 |
H1A—N1A—H3A | 109.5 | H1C—N1C—H2C | 109.5 |
H2A—N1A—H3A | 109.5 | H3C—N1C—H2C | 109.5 |
O2A—C1A—O1A | 125.0 (4) | O2C—C1C—O1C | 124.7 (3) |
O2A—C1A—C2A | 118.1 (4) | O2C—C1C—C2C | 116.9 (3) |
O1A—C1A—C2A | 116.8 (4) | O1C—C1C—C2C | 118.3 (3) |
N1A—C2A—C3A | 108.7 (3) | N1C—C2C—C3C | 110.9 (3) |
N1A—C2A—C1A | 109.2 (3) | N1C—C2C—C1C | 109.6 (3) |
C3A—C2A—C1A | 110.9 (3) | C3C—C2C—C1C | 111.2 (3) |
N1A—C2A—H21A | 109.3 | N1C—C2C—H21C | 108.4 |
C3A—C2A—H21A | 109.3 | C3C—C2C—H21C | 108.4 |
C1A—C2A—H21A | 109.3 | C1C—C2C—H21C | 108.4 |
C4A—C3A—C2A | 114.0 (4) | C4C—C3C—C2C | 114.6 (3) |
C4A—C3A—H32A | 108.8 | C4C—C3C—H31C | 108.6 |
C2A—C3A—H32A | 108.8 | C2C—C3C—H31C | 108.6 |
C4A—C3A—H31A | 108.8 | C4C—C3C—H32C | 108.6 |
C2A—C3A—H31A | 108.8 | C2C—C3C—H32C | 108.6 |
H32A—C3A—H31A | 107.7 | H31C—C3C—H32C | 107.6 |
C3A—C4A—H41A | 109.5 | C3C—C4C—H41C | 109.5 |
C3A—C4A—H42A | 109.5 | C3C—C4C—H42C | 109.5 |
H41A—C4A—H42A | 109.5 | H41C—C4C—H42C | 109.5 |
C3A—C4A—H43A | 109.5 | C3C—C4C—H43C | 109.5 |
H41A—C4A—H43A | 109.5 | H41C—C4C—H43C | 109.5 |
H42A—C4A—H43A | 109.5 | H42C—C4C—H43C | 109.5 |
C2B—N1B—H1B | 109.5 | C2D—N1D—H3D | 109.5 |
C2B—N1B—H2B | 109.5 | C2D—N1D—H2D | 109.5 |
H1B—N1B—H2B | 109.5 | H3D—N1D—H2D | 109.5 |
C2B—N1B—H3B | 109.5 | C2D—N1D—H1D | 109.5 |
H1B—N1B—H3B | 109.5 | H3D—N1D—H1D | 109.5 |
H2B—N1B—H3B | 109.5 | H2D—N1D—H1D | 109.5 |
O2B—C1B—O1B | 125.1 (4) | O2D—C1D—O1D | 124.5 (3) |
O2B—C1B—C2B | 117.4 (3) | O2D—C1D—C2D | 118.4 (3) |
O1B—C1B—C2B | 117.3 (3) | O1D—C1D—C2D | 117.0 (3) |
N1B—C2B—C3B | 110.7 (3) | N1D—C2D—C1D | 109.1 (3) |
N1B—C2B—C1B | 109.5 (3) | N1D—C2D—C3D | 108.9 (3) |
C3B—C2B—C1B | 108.6 (3) | C1D—C2D—C3D | 111.6 (3) |
N1B—C2B—H21B | 109.3 | N1D—C2D—H21D | 109.0 |
C3B—C2B—H21B | 109.3 | C1D—C2D—H21D | 109.0 |
C1B—C2B—H21B | 109.3 | C3D—C2D—H21D | 109.0 |
C4B—C3B—C2B | 114.2 (3) | C4D—C3D—C2D | 113.2 (3) |
C4B—C3B—H31B | 108.7 | C4D—C3D—H31D | 108.9 |
C2B—C3B—H31B | 108.7 | C2D—C3D—H31D | 108.9 |
C4B—C3B—H32B | 108.7 | C4D—C3D—H32D | 108.9 |
C2B—C3B—H32B | 108.7 | C2D—C3D—H32D | 108.9 |
H31B—C3B—H32B | 107.6 | H31D—C3D—H32D | 107.8 |
C3B—C4B—H41B | 109.5 | C3D—C4D—H41D | 109.5 |
C3B—C4B—H42B | 109.5 | C3D—C4D—H42D | 109.5 |
H41B—C4B—H42B | 109.5 | H41D—C4D—H42D | 109.5 |
C3B—C4B—H43B | 109.5 | C3D—C4D—H43D | 109.5 |
H41B—C4B—H43B | 109.5 | H41D—C4D—H43D | 109.5 |
H42B—C4B—H43B | 109.5 | H42D—C4D—H43D | 109.5 |
N1A—C2A—C1A—O1A | −28.9 (4) | O2B—C1B—C2B—N1B | 159.0 (3) |
N1A—C2A—C3A—C4A | −173.1 (3) | O2B—C1B—C2B—C3B | −80.0 (4) |
N1B—C2B—C1B—O1B | −25.5 (4) | O1B—C1B—C2B—C3B | 95.5 (4) |
N1B—C2B—C3B—C4B | −55.7 (4) | C1B—C2B—C3B—C4B | −176.0 (4) |
N1C—C2C—C1C—O1C | −13.0 (4) | O2C—C1C—C2C—N1C | 169.4 (3) |
N1C—C2C—C3C—C4C | 64.4 (4) | O2C—C1C—C2C—C3C | −67.6 (4) |
N1D—C2D—C1D—O1D | −30.6 (4) | O1C—C1C—C2C—C3C | 109.9 (4) |
N1D—C2D—C3D—C4D | −173.7 (3) | C1C—C2C—C3C—C4C | −57.8 (5) |
O2A—C1A—C2A—N1A | 154.1 (3) | O2D—C1D—C2D—N1D | 152.1 (3) |
O2A—C1A—C2A—C3A | −86.2 (4) | O2D—C1D—C2D—C3D | −87.5 (4) |
O1A—C1A—C2A—C3A | 90.9 (4) | O1D—C1D—C2D—C3D | 89.9 (4) |
C1A—C2A—C3A—C4A | 66.8 (4) | C1D—C2D—C3D—C4D | 65.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1Ai | 0.91 | 1.89 | 2.775 (4) | 162 |
N1A—H2A···O1Bii | 0.91 | 1.94 | 2.816 (4) | 160 |
N1A—H3A···O2Aii | 0.91 | 1.87 | 2.769 (4) | 168 |
N1B—H1B···O1Biii | 0.91 | 1.91 | 2.798 (4) | 163 |
N1B—H2B···O1Aiv | 0.91 | 1.92 | 2.799 (4) | 163 |
N1B—H3B···O2Bii | 0.91 | 1.87 | 2.773 (4) | 173 |
N1C—H1C···O1Dv | 0.91 | 1.98 | 2.824 (4) | 154 |
N1C—H2C···O2Cvi | 0.91 | 1.92 | 2.804 (4) | 164 |
N1C—H3C···O1Dvi | 0.91 | 1.94 | 2.821 (4) | 163 |
N1D—H1D···O1Cvii | 0.91 | 1.91 | 2.780 (4) | 160 |
N1D—H2D···O2Dvi | 0.91 | 1.87 | 2.756 (4) | 164 |
N1D—H3D···O1Civ | 0.91 | 1.95 | 2.817 (4) | 159 |
Symmetry codes: (i) −x, y, −z; (ii) x, y+1, z; (iii) −x+1, y, −z; (iv) x+1, y, z; (v) −x+1/2, y−1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+1/2, y+1/2, −z+1/2. |
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