




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810023639/lh5069sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810023639/lh5069Isup2.hkl |
CCDC reference: 786728
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.051
- wR factor = 0.167
- Data-to-parameter ratio = 23.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 42 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 84
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 600 Deg. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 1 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
The title compound was synthesised by the addition of sodium sulfite adduct of benzaldehyde (562 mg, 2.67 mmol) to a mixture of ethyl 3-amino-4-(2-hydroxylethylamino) benzoate (300 mg, 1.33 mmol) in 0.5 mL of DMF. Subsequently, the mixture was irradiated at 403K in a microwave reactor for 2 min. After the reaction, the mixture was diluted with 30 mL of EtOAc and washed with 20 mL of H2O. The organic layer was collected, dried over Na2SO4 and the solvent was evaporated under pressure to afford the crude product. The product was recrystallised with hot EtOAc which was slowly evaporated to give a single block of clear crystal.
The H atoms attached to O1A and O1B were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically [C-H = 0.93, 0.96 or 0.97 Å] and were refined using a riding model, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating group model was used for the methyl groups.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).
C18H18N2O3 | Z = 4 |
Mr = 310.34 | F(000) = 656 |
Triclinic, P1 | Dx = 1.334 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.997 (2) Å | Cell parameters from 6508 reflections |
b = 12.988 (3) Å | θ = 2.6–31.1° |
c = 15.030 (3) Å | µ = 0.09 mm−1 |
α = 103.764 (6)° | T = 100 K |
β = 107.202 (6)° | Block, colourless |
γ = 102.929 (6)° | 0.34 × 0.20 × 0.11 mm |
V = 1545.5 (6) Å3 |
Bruker APEXII DUO CCD area-detector diffractometer | 9838 independent reflections |
Radiation source: fine-focus sealed tube | 6952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ and ω scans | θmax = 31.1°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.970, Tmax = 0.990 | k = −18→18 |
34907 measured reflections | l = −21→21 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0944P)2 + 0.2365P] where P = (Fo2 + 2Fc2)/3 |
9838 reflections | (Δ/σ)max = 0.001 |
425 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C18H18N2O3 | γ = 102.929 (6)° |
Mr = 310.34 | V = 1545.5 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.997 (2) Å | Mo Kα radiation |
b = 12.988 (3) Å | µ = 0.09 mm−1 |
c = 15.030 (3) Å | T = 100 K |
α = 103.764 (6)° | 0.34 × 0.20 × 0.11 mm |
β = 107.202 (6)° |
Bruker APEXII DUO CCD area-detector diffractometer | 9838 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 6952 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.990 | Rint = 0.051 |
34907 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.41 e Å−3 |
9838 reflections | Δρmin = −0.40 e Å−3 |
425 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
O1A | 1.15213 (13) | 0.95597 (9) | 0.66787 (8) | 0.0189 (2) | |
O2A | 0.54072 (14) | 1.15419 (10) | 0.96176 (9) | 0.0311 (3) | |
O3A | 0.78042 (13) | 1.28774 (9) | 1.05882 (8) | 0.0235 (2) | |
N1A | 1.02010 (14) | 0.92733 (10) | 0.82790 (8) | 0.0147 (2) | |
N2A | 0.74895 (14) | 0.84883 (10) | 0.78666 (9) | 0.0155 (2) | |
C1A | 0.96687 (16) | 1.00752 (11) | 0.87590 (10) | 0.0148 (2) | |
C2A | 1.05169 (17) | 1.11622 (12) | 0.94178 (10) | 0.0171 (3) | |
H2AA | 1.1641 | 1.1480 | 0.9596 | 0.020* | |
C3A | 0.95920 (17) | 1.17389 (12) | 0.97904 (10) | 0.0171 (3) | |
H3AA | 1.0110 | 1.2462 | 1.0233 | 0.021* | |
C4A | 0.78835 (17) | 1.12585 (12) | 0.95159 (10) | 0.0160 (3) | |
C5A | 0.70664 (17) | 1.01725 (12) | 0.88665 (10) | 0.0161 (3) | |
H5AA | 0.5943 | 0.9853 | 0.8689 | 0.019* | |
C6A | 0.79750 (16) | 0.95790 (12) | 0.84909 (10) | 0.0150 (3) | |
C7A | 0.88525 (16) | 0.83316 (11) | 0.77649 (10) | 0.0149 (3) | |
C8A | 0.88701 (16) | 0.72261 (11) | 0.72397 (10) | 0.0161 (3) | |
C9A | 0.78407 (17) | 0.62979 (12) | 0.73233 (11) | 0.0192 (3) | |
H9AA | 0.7178 | 0.6404 | 0.7686 | 0.023* | |
C10A | 0.78010 (19) | 0.52256 (13) | 0.68722 (12) | 0.0219 (3) | |
H10A | 0.7113 | 0.4616 | 0.6931 | 0.026* | |
C11A | 0.87878 (19) | 0.50601 (13) | 0.63319 (12) | 0.0234 (3) | |
H11A | 0.8785 | 0.4342 | 0.6043 | 0.028* | |
C12A | 0.97797 (19) | 0.59712 (13) | 0.62236 (12) | 0.0235 (3) | |
H12A | 1.0425 | 0.5858 | 0.5850 | 0.028* | |
C13A | 0.98171 (18) | 0.70472 (12) | 0.66663 (11) | 0.0195 (3) | |
H13A | 1.0474 | 0.7651 | 0.6582 | 0.023* | |
C14A | 1.19033 (16) | 0.94750 (12) | 0.83426 (10) | 0.0170 (3) | |
H14A | 1.2089 | 0.8763 | 0.8138 | 0.020* | |
H14B | 1.2633 | 0.9868 | 0.9023 | 0.020* | |
C15A | 1.23125 (17) | 1.01573 (12) | 0.77022 (10) | 0.0178 (3) | |
H15A | 1.1993 | 1.0824 | 0.7850 | 0.021* | |
H15B | 1.3490 | 1.0392 | 0.7867 | 0.021* | |
C16A | 0.68862 (19) | 1.18841 (12) | 0.98976 (11) | 0.0195 (3) | |
C17A | 0.6900 (2) | 1.35453 (14) | 1.09824 (13) | 0.0270 (3) | |
H17A | 0.6001 | 1.3559 | 1.0441 | 0.032* | |
H17B | 0.7622 | 1.4307 | 1.1334 | 0.032* | |
C18A | 0.6227 (2) | 1.30985 (16) | 1.16688 (13) | 0.0309 (4) | |
H18A | 0.5706 | 1.3591 | 1.1944 | 0.046* | |
H18B | 0.7105 | 1.3051 | 1.2190 | 0.046* | |
H18C | 0.5438 | 1.2369 | 1.1310 | 0.046* | |
O1B | 0.44589 (13) | 0.70587 (9) | 0.63176 (8) | 0.0198 (2) | |
O2B | 0.98042 (13) | 1.37266 (9) | 0.85047 (9) | 0.0261 (2) | |
O3B | 0.72718 (13) | 1.37041 (9) | 0.84618 (8) | 0.0218 (2) | |
N1B | 0.56260 (14) | 0.88812 (10) | 0.55835 (8) | 0.0146 (2) | |
N2B | 0.83526 (14) | 0.96642 (10) | 0.60695 (9) | 0.0159 (2) | |
C1B | 0.60025 (16) | 0.99572 (11) | 0.61970 (10) | 0.0144 (2) | |
C2B | 0.50052 (16) | 1.05442 (12) | 0.64814 (10) | 0.0163 (3) | |
H2BA | 0.3873 | 1.0224 | 0.6255 | 0.020* | |
C3B | 0.57926 (17) | 1.16295 (12) | 0.71190 (10) | 0.0170 (3) | |
H3BA | 0.5174 | 1.2055 | 0.7320 | 0.020* | |
C4B | 0.75098 (17) | 1.21029 (11) | 0.74702 (10) | 0.0158 (3) | |
C5B | 0.84839 (16) | 1.15126 (11) | 0.71697 (10) | 0.0155 (3) | |
H5BA | 0.9618 | 1.1830 | 0.7404 | 0.019* | |
C6B | 0.77088 (16) | 1.04313 (11) | 0.65068 (10) | 0.0146 (2) | |
C7B | 0.70751 (16) | 0.87512 (11) | 0.55223 (10) | 0.0150 (3) | |
C8B | 0.72348 (17) | 0.77623 (12) | 0.48846 (10) | 0.0169 (3) | |
C9B | 0.83211 (19) | 0.79407 (13) | 0.43951 (12) | 0.0235 (3) | |
H9BA | 0.8894 | 0.8666 | 0.4467 | 0.028* | |
C10B | 0.8546 (2) | 0.70370 (15) | 0.38006 (13) | 0.0299 (4) | |
H10B | 0.9284 | 0.7160 | 0.3486 | 0.036* | |
C11B | 0.7677 (2) | 0.59535 (14) | 0.36748 (13) | 0.0270 (3) | |
H11B | 0.7813 | 0.5352 | 0.3264 | 0.032* | |
C12B | 0.66018 (19) | 0.57676 (13) | 0.41618 (12) | 0.0224 (3) | |
H12B | 0.6027 | 0.5040 | 0.4082 | 0.027* | |
C13B | 0.63813 (17) | 0.66645 (12) | 0.47681 (11) | 0.0187 (3) | |
H13B | 0.5666 | 0.6536 | 0.5097 | 0.022* | |
C14B | 0.39725 (16) | 0.80879 (12) | 0.51552 (10) | 0.0166 (3) | |
H14C | 0.3917 | 0.7454 | 0.4636 | 0.020* | |
H14D | 0.3204 | 0.8442 | 0.4864 | 0.020* | |
C15B | 0.34895 (17) | 0.76807 (12) | 0.59306 (11) | 0.0187 (3) | |
H15C | 0.3599 | 0.8320 | 0.6463 | 0.022* | |
H15D | 0.2347 | 0.7220 | 0.5639 | 0.022* | |
C16B | 0.83472 (18) | 1.32504 (12) | 0.81937 (10) | 0.0179 (3) | |
C17B | 0.7947 (2) | 1.48136 (13) | 0.91805 (12) | 0.0243 (3) | |
H17C | 0.8708 | 1.5301 | 0.9000 | 0.029* | |
H17D | 0.8527 | 1.4787 | 0.9827 | 0.029* | |
C18B | 0.6526 (2) | 1.52376 (16) | 0.91910 (15) | 0.0354 (4) | |
H18D | 0.6924 | 1.5977 | 0.9659 | 0.053* | |
H18E | 0.5786 | 1.4750 | 0.9374 | 0.053* | |
H18F | 0.5960 | 1.5256 | 0.8547 | 0.053* | |
H1OA | 1.061 (3) | 0.9613 (18) | 0.6519 (16) | 0.033 (6)* | |
H1OB | 0.551 (3) | 0.753 (2) | 0.6837 (18) | 0.048 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0133 (5) | 0.0260 (5) | 0.0181 (5) | 0.0069 (4) | 0.0064 (4) | 0.0070 (4) |
O2A | 0.0197 (5) | 0.0316 (6) | 0.0346 (7) | 0.0082 (5) | 0.0096 (5) | −0.0017 (5) |
O3A | 0.0230 (5) | 0.0193 (5) | 0.0255 (6) | 0.0058 (4) | 0.0114 (4) | 0.0006 (4) |
N1A | 0.0137 (5) | 0.0153 (5) | 0.0152 (5) | 0.0043 (4) | 0.0061 (4) | 0.0048 (4) |
N2A | 0.0133 (5) | 0.0161 (5) | 0.0162 (5) | 0.0036 (4) | 0.0058 (4) | 0.0045 (4) |
C1A | 0.0155 (6) | 0.0160 (6) | 0.0139 (6) | 0.0049 (5) | 0.0064 (5) | 0.0055 (5) |
C2A | 0.0146 (6) | 0.0178 (6) | 0.0168 (6) | 0.0031 (5) | 0.0047 (5) | 0.0056 (5) |
C3A | 0.0178 (6) | 0.0164 (6) | 0.0152 (6) | 0.0036 (5) | 0.0055 (5) | 0.0042 (5) |
C4A | 0.0169 (6) | 0.0176 (6) | 0.0142 (6) | 0.0058 (5) | 0.0059 (5) | 0.0056 (5) |
C5A | 0.0140 (6) | 0.0183 (6) | 0.0158 (6) | 0.0046 (5) | 0.0053 (5) | 0.0059 (5) |
C6A | 0.0148 (6) | 0.0162 (6) | 0.0135 (6) | 0.0041 (5) | 0.0048 (5) | 0.0051 (5) |
C7A | 0.0143 (6) | 0.0164 (6) | 0.0144 (6) | 0.0038 (5) | 0.0056 (5) | 0.0061 (5) |
C8A | 0.0141 (6) | 0.0163 (6) | 0.0166 (6) | 0.0051 (5) | 0.0038 (5) | 0.0052 (5) |
C9A | 0.0179 (6) | 0.0194 (7) | 0.0204 (7) | 0.0046 (5) | 0.0077 (5) | 0.0073 (5) |
C10A | 0.0207 (7) | 0.0168 (7) | 0.0262 (7) | 0.0038 (5) | 0.0072 (6) | 0.0076 (6) |
C11A | 0.0223 (7) | 0.0171 (7) | 0.0274 (8) | 0.0052 (6) | 0.0080 (6) | 0.0035 (6) |
C12A | 0.0230 (7) | 0.0211 (7) | 0.0277 (8) | 0.0072 (6) | 0.0137 (6) | 0.0044 (6) |
C13A | 0.0190 (6) | 0.0180 (7) | 0.0215 (7) | 0.0046 (5) | 0.0091 (6) | 0.0054 (5) |
C14A | 0.0131 (6) | 0.0204 (7) | 0.0187 (6) | 0.0060 (5) | 0.0068 (5) | 0.0068 (5) |
C15A | 0.0131 (6) | 0.0211 (7) | 0.0196 (7) | 0.0040 (5) | 0.0071 (5) | 0.0071 (5) |
C16A | 0.0227 (7) | 0.0199 (7) | 0.0163 (6) | 0.0079 (5) | 0.0077 (5) | 0.0049 (5) |
C17A | 0.0333 (8) | 0.0218 (7) | 0.0321 (8) | 0.0130 (6) | 0.0202 (7) | 0.0055 (6) |
C18A | 0.0329 (9) | 0.0348 (9) | 0.0279 (8) | 0.0157 (7) | 0.0129 (7) | 0.0084 (7) |
O1B | 0.0212 (5) | 0.0172 (5) | 0.0204 (5) | 0.0043 (4) | 0.0072 (4) | 0.0073 (4) |
O2B | 0.0185 (5) | 0.0217 (6) | 0.0302 (6) | 0.0023 (4) | 0.0064 (5) | 0.0019 (5) |
O3B | 0.0196 (5) | 0.0198 (5) | 0.0242 (5) | 0.0064 (4) | 0.0088 (4) | 0.0032 (4) |
N1B | 0.0121 (5) | 0.0158 (5) | 0.0157 (5) | 0.0033 (4) | 0.0054 (4) | 0.0057 (4) |
N2B | 0.0138 (5) | 0.0166 (6) | 0.0178 (6) | 0.0048 (4) | 0.0059 (4) | 0.0067 (4) |
C1B | 0.0130 (6) | 0.0158 (6) | 0.0145 (6) | 0.0033 (5) | 0.0046 (5) | 0.0066 (5) |
C2B | 0.0127 (6) | 0.0202 (7) | 0.0169 (6) | 0.0051 (5) | 0.0060 (5) | 0.0072 (5) |
C3B | 0.0160 (6) | 0.0194 (7) | 0.0177 (6) | 0.0065 (5) | 0.0077 (5) | 0.0071 (5) |
C4B | 0.0168 (6) | 0.0156 (6) | 0.0148 (6) | 0.0038 (5) | 0.0060 (5) | 0.0053 (5) |
C5B | 0.0131 (6) | 0.0171 (6) | 0.0163 (6) | 0.0036 (5) | 0.0046 (5) | 0.0073 (5) |
C6B | 0.0127 (6) | 0.0167 (6) | 0.0161 (6) | 0.0049 (5) | 0.0057 (5) | 0.0078 (5) |
C7B | 0.0133 (6) | 0.0172 (6) | 0.0163 (6) | 0.0051 (5) | 0.0055 (5) | 0.0080 (5) |
C8B | 0.0154 (6) | 0.0186 (7) | 0.0173 (6) | 0.0054 (5) | 0.0064 (5) | 0.0063 (5) |
C9B | 0.0247 (7) | 0.0223 (7) | 0.0304 (8) | 0.0085 (6) | 0.0165 (6) | 0.0118 (6) |
C10B | 0.0358 (9) | 0.0295 (8) | 0.0367 (9) | 0.0138 (7) | 0.0267 (8) | 0.0123 (7) |
C11B | 0.0291 (8) | 0.0244 (8) | 0.0288 (8) | 0.0112 (6) | 0.0143 (7) | 0.0038 (6) |
C12B | 0.0209 (7) | 0.0178 (7) | 0.0270 (8) | 0.0052 (5) | 0.0089 (6) | 0.0053 (6) |
C13B | 0.0170 (6) | 0.0190 (7) | 0.0212 (7) | 0.0055 (5) | 0.0081 (5) | 0.0073 (5) |
C14B | 0.0117 (6) | 0.0183 (6) | 0.0177 (6) | 0.0026 (5) | 0.0043 (5) | 0.0054 (5) |
C15B | 0.0160 (6) | 0.0189 (7) | 0.0224 (7) | 0.0032 (5) | 0.0099 (5) | 0.0074 (5) |
C16B | 0.0191 (6) | 0.0175 (6) | 0.0177 (6) | 0.0058 (5) | 0.0069 (5) | 0.0070 (5) |
C17B | 0.0266 (8) | 0.0190 (7) | 0.0251 (8) | 0.0071 (6) | 0.0107 (6) | 0.0022 (6) |
C18B | 0.0384 (10) | 0.0310 (9) | 0.0467 (11) | 0.0165 (8) | 0.0253 (9) | 0.0126 (8) |
O1A—C15A | 1.4186 (18) | O1B—C15B | 1.4109 (18) |
O1A—H1OA | 0.81 (2) | O1B—H1OB | 0.98 (3) |
O2A—C16A | 1.2085 (19) | O2B—C16B | 1.2069 (18) |
O3A—C16A | 1.3427 (18) | O3B—C16B | 1.3484 (18) |
O3A—C17A | 1.4564 (18) | O3B—C17B | 1.4463 (19) |
N1A—C7A | 1.3772 (18) | N1B—C7B | 1.3779 (17) |
N1A—C1A | 1.3801 (17) | N1B—C1B | 1.3815 (18) |
N1A—C14A | 1.4647 (18) | N1B—C14B | 1.4563 (17) |
N2A—C7A | 1.3328 (18) | N2B—C7B | 1.3306 (18) |
N2A—C6A | 1.3879 (18) | N2B—C6B | 1.3900 (18) |
C1A—C2A | 1.4007 (19) | C1B—C2B | 1.3953 (19) |
C1A—C6A | 1.4048 (19) | C1B—C6B | 1.4037 (18) |
C2A—C3A | 1.386 (2) | C2B—C3B | 1.384 (2) |
C2A—H2AA | 0.9300 | C2B—H2BA | 0.9300 |
C3A—C4A | 1.413 (2) | C3B—C4B | 1.408 (2) |
C3A—H3AA | 0.9300 | C3B—H3BA | 0.9300 |
C4A—C5A | 1.393 (2) | C4B—C5B | 1.3892 (19) |
C4A—C16A | 1.484 (2) | C4B—C16B | 1.488 (2) |
C5A—C6A | 1.3889 (19) | C5B—C6B | 1.3915 (19) |
C5A—H5AA | 0.9300 | C5B—H5BA | 0.9300 |
C7A—C8A | 1.471 (2) | C7B—C8B | 1.472 (2) |
C8A—C13A | 1.396 (2) | C8B—C9B | 1.398 (2) |
C8A—C9A | 1.4030 (19) | C8B—C13B | 1.402 (2) |
C9A—C10A | 1.384 (2) | C9B—C10B | 1.390 (2) |
C9A—H9AA | 0.9300 | C9B—H9BA | 0.9300 |
C10A—C11A | 1.387 (2) | C10B—C11B | 1.386 (2) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—C12A | 1.389 (2) | C11B—C12B | 1.388 (2) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.386 (2) | C12B—C13B | 1.390 (2) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.522 (2) | C14B—C15B | 1.5221 (19) |
C14A—H14A | 0.9700 | C14B—H14C | 0.9700 |
C14A—H14B | 0.9700 | C14B—H14D | 0.9700 |
C15A—H15A | 0.9700 | C15B—H15C | 0.9700 |
C15A—H15B | 0.9700 | C15B—H15D | 0.9700 |
C17A—C18A | 1.505 (2) | C17B—C18B | 1.504 (2) |
C17A—H17A | 0.9700 | C17B—H17C | 0.9700 |
C17A—H17B | 0.9700 | C17B—H17D | 0.9700 |
C18A—H18A | 0.9600 | C18B—H18D | 0.9600 |
C18A—H18B | 0.9600 | C18B—H18E | 0.9600 |
C18A—H18C | 0.9600 | C18B—H18F | 0.9600 |
C15A—O1A—H1OA | 106.6 (15) | C15B—O1B—H1OB | 112.7 (14) |
C16A—O3A—C17A | 115.62 (13) | C16B—O3B—C17B | 116.69 (12) |
C7A—N1A—C1A | 106.75 (11) | C7B—N1B—C1B | 106.88 (11) |
C7A—N1A—C14A | 130.19 (12) | C7B—N1B—C14B | 130.48 (12) |
C1A—N1A—C14A | 123.05 (12) | C1B—N1B—C14B | 122.60 (11) |
C7A—N2A—C6A | 105.31 (11) | C7B—N2B—C6B | 105.39 (11) |
N1A—C1A—C2A | 131.57 (13) | N1B—C1B—C2B | 131.25 (12) |
N1A—C1A—C6A | 105.94 (12) | N1B—C1B—C6B | 105.80 (12) |
C2A—C1A—C6A | 122.46 (13) | C2B—C1B—C6B | 122.93 (13) |
C3A—C2A—C1A | 116.44 (13) | C3B—C2B—C1B | 116.39 (13) |
C3A—C2A—H2AA | 121.8 | C3B—C2B—H2BA | 121.8 |
C1A—C2A—H2AA | 121.8 | C1B—C2B—H2BA | 121.8 |
C2A—C3A—C4A | 121.80 (13) | C2B—C3B—C4B | 121.44 (13) |
C2A—C3A—H3AA | 119.1 | C2B—C3B—H3BA | 119.3 |
C4A—C3A—H3AA | 119.1 | C4B—C3B—H3BA | 119.3 |
C5A—C4A—C3A | 120.83 (13) | C5B—C4B—C3B | 121.46 (13) |
C5A—C4A—C16A | 117.33 (13) | C5B—C4B—C16B | 117.66 (12) |
C3A—C4A—C16A | 121.83 (13) | C3B—C4B—C16B | 120.88 (13) |
C6A—C5A—C4A | 118.18 (13) | C4B—C5B—C6B | 117.88 (12) |
C6A—C5A—H5AA | 120.9 | C4B—C5B—H5BA | 121.1 |
C4A—C5A—H5AA | 120.9 | C6B—C5B—H5BA | 121.1 |
N2A—C6A—C5A | 130.04 (13) | N2B—C6B—C5B | 130.50 (12) |
N2A—C6A—C1A | 109.67 (12) | N2B—C6B—C1B | 109.69 (12) |
C5A—C6A—C1A | 120.28 (13) | C5B—C6B—C1B | 119.80 (12) |
N2A—C7A—N1A | 112.31 (12) | N2B—C7B—N1B | 112.22 (12) |
N2A—C7A—C8A | 121.48 (12) | N2B—C7B—C8B | 122.11 (12) |
N1A—C7A—C8A | 125.92 (12) | N1B—C7B—C8B | 125.54 (12) |
C13A—C8A—C9A | 118.79 (13) | C9B—C8B—C13B | 119.22 (13) |
C13A—C8A—C7A | 124.62 (13) | C9B—C8B—C7B | 117.73 (13) |
C9A—C8A—C7A | 116.59 (12) | C13B—C8B—C7B | 123.04 (12) |
C10A—C9A—C8A | 120.72 (14) | C10B—C9B—C8B | 120.14 (14) |
C10A—C9A—H9AA | 119.6 | C10B—C9B—H9BA | 119.9 |
C8A—C9A—H9AA | 119.6 | C8B—C9B—H9BA | 119.9 |
C9A—C10A—C11A | 119.98 (14) | C11B—C10B—C9B | 120.35 (15) |
C9A—C10A—H10A | 120.0 | C11B—C10B—H10B | 119.8 |
C11A—C10A—H10A | 120.0 | C9B—C10B—H10B | 119.8 |
C10A—C11A—C12A | 119.75 (14) | C10B—C11B—C12B | 119.94 (15) |
C10A—C11A—H11A | 120.1 | C10B—C11B—H11B | 120.0 |
C12A—C11A—H11A | 120.1 | C12B—C11B—H11B | 120.0 |
C13A—C12A—C11A | 120.63 (14) | C11B—C12B—C13B | 120.24 (14) |
C13A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.9 |
C11A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.9 |
C12A—C13A—C8A | 120.08 (13) | C12B—C13B—C8B | 120.10 (13) |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 120.0 |
C8A—C13A—H13A | 120.0 | C8B—C13B—H13B | 120.0 |
N1A—C14A—C15A | 112.25 (11) | N1B—C14B—C15B | 111.15 (11) |
N1A—C14A—H14A | 109.2 | N1B—C14B—H14C | 109.4 |
C15A—C14A—H14A | 109.2 | C15B—C14B—H14C | 109.4 |
N1A—C14A—H14B | 109.2 | N1B—C14B—H14D | 109.4 |
C15A—C14A—H14B | 109.2 | C15B—C14B—H14D | 109.4 |
H14A—C14A—H14B | 107.9 | H14C—C14B—H14D | 108.0 |
O1A—C15A—C14A | 113.10 (12) | O1B—C15B—C14B | 112.51 (11) |
O1A—C15A—H15A | 109.0 | O1B—C15B—H15C | 109.1 |
C14A—C15A—H15A | 109.0 | C14B—C15B—H15C | 109.1 |
O1A—C15A—H15B | 109.0 | O1B—C15B—H15D | 109.1 |
C14A—C15A—H15B | 109.0 | C14B—C15B—H15D | 109.1 |
H15A—C15A—H15B | 107.8 | H15C—C15B—H15D | 107.8 |
O2A—C16A—O3A | 123.39 (14) | O2B—C16B—O3B | 123.64 (14) |
O2A—C16A—C4A | 123.88 (14) | O2B—C16B—C4B | 124.81 (14) |
O3A—C16A—C4A | 112.73 (13) | O3B—C16B—C4B | 111.55 (12) |
O3A—C17A—C18A | 112.42 (14) | O3B—C17B—C18B | 106.85 (14) |
O3A—C17A—H17A | 109.1 | O3B—C17B—H17C | 110.4 |
C18A—C17A—H17A | 109.1 | C18B—C17B—H17C | 110.4 |
O3A—C17A—H17B | 109.1 | O3B—C17B—H17D | 110.4 |
C18A—C17A—H17B | 109.1 | C18B—C17B—H17D | 110.4 |
H17A—C17A—H17B | 107.9 | H17C—C17B—H17D | 108.6 |
C17A—C18A—H18A | 109.5 | C17B—C18B—H18D | 109.5 |
C17A—C18A—H18B | 109.5 | C17B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C17A—C18A—H18C | 109.5 | C17B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C7A—N1A—C1A—C2A | 176.50 (14) | C7B—N1B—C1B—C2B | 177.03 (14) |
C14A—N1A—C1A—C2A | −4.2 (2) | C14B—N1B—C1B—C2B | −5.3 (2) |
C7A—N1A—C1A—C6A | −1.25 (14) | C7B—N1B—C1B—C6B | −1.51 (14) |
C14A—N1A—C1A—C6A | 178.06 (12) | C14B—N1B—C1B—C6B | 176.20 (11) |
N1A—C1A—C2A—C3A | −178.13 (13) | N1B—C1B—C2B—C3B | 179.89 (13) |
C6A—C1A—C2A—C3A | −0.7 (2) | C6B—C1B—C2B—C3B | −1.8 (2) |
C1A—C2A—C3A—C4A | −0.4 (2) | C1B—C2B—C3B—C4B | −1.0 (2) |
C2A—C3A—C4A—C5A | 1.0 (2) | C2B—C3B—C4B—C5B | 1.9 (2) |
C2A—C3A—C4A—C16A | −178.65 (13) | C2B—C3B—C4B—C16B | −176.95 (13) |
C3A—C4A—C5A—C6A | −0.5 (2) | C3B—C4B—C5B—C6B | 0.0 (2) |
C16A—C4A—C5A—C6A | 179.14 (12) | C16B—C4B—C5B—C6B | 178.85 (12) |
C7A—N2A—C6A—C5A | −178.09 (14) | C7B—N2B—C6B—C5B | 178.20 (14) |
C7A—N2A—C6A—C1A | 0.21 (15) | C7B—N2B—C6B—C1B | −0.70 (15) |
C4A—C5A—C6A—N2A | 177.63 (13) | C4B—C5B—C6B—N2B | 178.57 (13) |
C4A—C5A—C6A—C1A | −0.5 (2) | C4B—C5B—C6B—C1B | −2.63 (19) |
N1A—C1A—C6A—N2A | 0.67 (15) | N1B—C1B—C6B—N2B | 1.40 (14) |
C2A—C1A—C6A—N2A | −177.34 (12) | C2B—C1B—C6B—N2B | −177.30 (12) |
N1A—C1A—C6A—C5A | 179.17 (12) | N1B—C1B—C6B—C5B | −177.64 (12) |
C2A—C1A—C6A—C5A | 1.2 (2) | C2B—C1B—C6B—C5B | 3.7 (2) |
C6A—N2A—C7A—N1A | −1.05 (15) | C6B—N2B—C7B—N1B | −0.29 (15) |
C6A—N2A—C7A—C8A | 173.07 (12) | C6B—N2B—C7B—C8B | 175.92 (12) |
C1A—N1A—C7A—N2A | 1.49 (15) | C1B—N1B—C7B—N2B | 1.17 (15) |
C14A—N1A—C7A—N2A | −177.76 (12) | C14B—N1B—C7B—N2B | −176.30 (12) |
C1A—N1A—C7A—C8A | −172.31 (12) | C1B—N1B—C7B—C8B | −174.89 (12) |
C14A—N1A—C7A—C8A | 8.4 (2) | C14B—N1B—C7B—C8B | 7.6 (2) |
N2A—C7A—C8A—C13A | 145.39 (14) | N2B—C7B—C8B—C9B | −37.4 (2) |
N1A—C7A—C8A—C13A | −41.3 (2) | N1B—C7B—C8B—C9B | 138.34 (15) |
N2A—C7A—C8A—C9A | −33.94 (19) | N2B—C7B—C8B—C13B | 141.16 (14) |
N1A—C7A—C8A—C9A | 139.34 (14) | N1B—C7B—C8B—C13B | −43.1 (2) |
C13A—C8A—C9A—C10A | 2.0 (2) | C13B—C8B—C9B—C10B | 0.0 (2) |
C7A—C8A—C9A—C10A | −178.61 (13) | C7B—C8B—C9B—C10B | 178.61 (15) |
C8A—C9A—C10A—C11A | 0.1 (2) | C8B—C9B—C10B—C11B | 1.1 (3) |
C9A—C10A—C11A—C12A | −1.8 (2) | C9B—C10B—C11B—C12B | −1.4 (3) |
C10A—C11A—C12A—C13A | 1.3 (2) | C10B—C11B—C12B—C13B | 0.6 (3) |
C11A—C12A—C13A—C8A | 0.9 (2) | C11B—C12B—C13B—C8B | 0.5 (2) |
C9A—C8A—C13A—C12A | −2.5 (2) | C9B—C8B—C13B—C12B | −0.8 (2) |
C7A—C8A—C13A—C12A | 178.16 (14) | C7B—C8B—C13B—C12B | −179.33 (13) |
C7A—N1A—C14A—C15A | 102.15 (16) | C7B—N1B—C14B—C15B | 104.85 (16) |
C1A—N1A—C14A—C15A | −76.99 (16) | C1B—N1B—C14B—C15B | −72.28 (16) |
N1A—C14A—C15A—O1A | −69.79 (15) | N1B—C14B—C15B—O1B | −64.92 (15) |
C17A—O3A—C16A—O2A | −0.9 (2) | C17B—O3B—C16B—O2B | −1.5 (2) |
C17A—O3A—C16A—C4A | 178.92 (12) | C17B—O3B—C16B—C4B | 178.76 (12) |
C5A—C4A—C16A—O2A | −6.3 (2) | C5B—C4B—C16B—O2B | 3.6 (2) |
C3A—C4A—C16A—O2A | 173.36 (14) | C3B—C4B—C16B—O2B | −177.50 (14) |
C5A—C4A—C16A—O3A | 173.93 (12) | C5B—C4B—C16B—O3B | −176.65 (12) |
C3A—C4A—C16A—O3A | −6.43 (19) | C3B—C4B—C16B—O3B | 2.24 (19) |
C16A—O3A—C17A—C18A | 73.83 (18) | C16B—O3B—C17B—C18B | 167.61 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N2B | 0.81 (3) | 1.96 (3) | 2.7700 (19) | 177 (3) |
O1B—H1OB···N2A | 0.98 (3) | 1.89 (3) | 2.8680 (18) | 177 (2) |
C2B—H2BA···O1Ai | 0.93 | 2.42 | 3.238 (2) | 146 |
C12B—H12B···O1Bii | 0.93 | 2.55 | 3.416 (2) | 155 |
C13A—H13A···O1A | 0.93 | 2.40 | 3.273 (2) | 157 |
C13B—H13B···O1B | 0.93 | 2.43 | 3.300 (2) | 155 |
C15A—H15B···O2Aiii | 0.97 | 2.53 | 3.135 (2) | 120 |
C17B—H17D···O2Biv | 0.97 | 2.54 | 3.282 (2) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+3, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H18N2O3 |
Mr | 310.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.997 (2), 12.988 (3), 15.030 (3) |
α, β, γ (°) | 103.764 (6), 107.202 (6), 102.929 (6) |
V (Å3) | 1545.5 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.34 × 0.20 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.970, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34907, 9838, 6952 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.727 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.167, 1.04 |
No. of reflections | 9838 |
No. of parameters | 425 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N2B | 0.81 (3) | 1.96 (3) | 2.7700 (19) | 177 (3) |
O1B—H1OB···N2A | 0.98 (3) | 1.89 (3) | 2.8680 (18) | 177 (2) |
C2B—H2BA···O1Ai | 0.9300 | 2.4200 | 3.238 (2) | 146.00 |
C12B—H12B···O1Bii | 0.9300 | 2.5500 | 3.416 (2) | 155.00 |
C13A—H13A···O1A | 0.9300 | 2.4000 | 3.273 (2) | 157.00 |
C13B—H13B···O1B | 0.9300 | 2.4300 | 3.300 (2) | 155.00 |
C15A—H15B···O2Aiii | 0.9700 | 2.5300 | 3.135 (2) | 120.00 |
C17B—H17D···O2Biv | 0.9700 | 2.5400 | 3.282 (2) | 133.00 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+3, −z+2. |
Benzimidazole and its derivatives are compounds which are well known in the pharmaceutical and biological fields (Horton et al., 2003). These heterocycles can serve as molecular scaffolds with versatile binding properties via modifications of their functional groups (DeSimone et al., 2004). Suitably substituted benzimidazole derivatives have been reported to show anti-tumor (Gowda et al., 2009), antimicrobial (Tunçbilek et al., 2009) and anti-inflammatory (Achar et al., 2010) activities. On this basis, we report the structure of the title compound.
The asymmetric unit of (I) contains two molecules (Fig. 1) [A and B] with all geometrical parameters within normal ranges. For both molecules, the benzimidazole ring system (N1/N2/C1–C7) is essentially planar with a maximum deviation of 0.027 (1) and 0.032 (1)Å respectively for atom C7A and N1B. The dihedral angle between the benzimidazole ring system (N1/N2/C1–C7) and the attached benzene ring (C8–C13) is 38.64 (6) and 41.48 (6)° respectively for molecules A and B.
The two independent molecules are connected into a dimer by two intermolecular O—H···N hydrogen bonds (Table 1). In the crystal structure, molecules are connected by weak intermolecular C—H···O interactions (Table 1). These interactions form two-dimensional layers parallel to (0 1 2). In addition there are weak π···π stacking interactions within the asymmetric unit with distances of Cg1···Cg3 = 3.5244 (12) Å and Cg2···Cg4 = 3.6189 (12) Å; Cg1, Cg2, Cg3 and Cg4 and are the centroids of N1A/N2A/C1A/C6A–C7A, C1A–C6A, N1B/N2B/C1B/C6B–C7B and C1B–C6B rings, respectively.