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The single-crystal structure of the title compound, C24H37NO7, which is a derivative of the commonly used chelating agent amino­phenol tri­acetic acid, has been determined. The structure was solved in space group P\overline 1 with two mol­ecules in the unit cell. As expected, the geometric conform­ation of this derivative of the free ligand differs extensively from that of the coordinated form.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021652/fl6062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021652/fl6062Isup2.hkl
Contains datablock I

CCDC reference: 226953

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.124
  • Data-to-parameter ratio = 26.1

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD 170 (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD 170; data reduction: CrysAlis RED 170 (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Di-tert-butyl 2-(tert-butyloxycarbonylmethoxy)phenyliminodiacetate top
Crystal data top
C24H37NO7Z = 2
Mr = 451.55F(000) = 488
Triclinic, P1Dx = 1.212 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.559 (5) ÅCell parameters from 559 reflections
b = 11.192 (4) Åθ = 2–31°
c = 13.689 (5) ŵ = 0.09 mm1
α = 106.03 (3)°T = 120 K
β = 96.27 (4)°Block, colourless
γ = 96.89 (4)°0.55 × 0.40 × 0.30 mm
V = 1237.2 (10) Å3
Data collection top
Oxford Excalibur2
diffractometer
5991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 31.9°, θmin = 4.6°
ω–2θ scansh = 1210
12422 measured reflectionsk = 1616
7546 independent reflectionsl = 1820
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.0751P]
where P = (Fo2 + 2Fc2)/3
7546 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
C190.66254 (11)0.81114 (9)0.22112 (7)0.01562 (17)
H19A0.75460.81210.27200.019*
H19B0.64000.72670.17020.019*
C200.51860 (11)0.83377 (9)0.27576 (7)0.01585 (17)
C210.34185 (12)0.72855 (10)0.36691 (8)0.01969 (19)
C220.35213 (14)0.61003 (11)0.39987 (9)0.0282 (2)
H22A0.44990.62260.44840.042*
H22B0.35340.53880.33940.042*
H22C0.25970.59240.43300.042*
C230.35103 (14)0.84193 (11)0.46051 (9)0.0261 (2)
H23A0.44920.85010.50760.039*
H23B0.25900.83060.49570.039*
H23C0.35080.91820.43860.039*
C240.19429 (13)0.71099 (12)0.28844 (9)0.0284 (2)
H24A0.19520.63790.22940.043*
H24B0.19370.78640.26530.043*
H24C0.09890.69740.32000.043*
O60.44689 (9)0.92101 (7)0.28196 (6)0.02078 (15)
O70.48558 (8)0.73897 (7)0.31686 (5)0.01860 (15)
C10.78470 (10)0.86391 (8)0.08297 (7)0.01405 (17)
C20.86789 (11)0.76264 (9)0.06951 (7)0.01751 (18)
H20.87730.72140.12140.021*
C30.93778 (12)0.72028 (10)0.01839 (8)0.02060 (19)
H30.99250.64990.02680.025*
C40.92698 (12)0.78142 (10)0.09341 (8)0.02063 (19)
H40.97520.75330.15320.025*
C50.84594 (12)0.88382 (9)0.08179 (7)0.01837 (18)
H50.83920.92560.13350.022*
C60.77458 (11)0.92521 (8)0.00562 (7)0.01487 (17)
C70.68334 (12)1.09485 (9)0.04805 (7)0.01804 (18)
H7A0.59541.05210.10490.022*
H7B0.78371.09850.07760.022*
C80.65502 (11)1.22704 (9)0.00258 (7)0.01774 (18)
C90.63504 (12)1.37702 (9)0.16768 (8)0.02029 (19)
C100.77988 (13)1.47156 (10)0.16986 (10)0.0295 (2)
H10A0.87651.44340.19480.044*
H10B0.77101.55400.21580.044*
H10C0.78541.47810.10040.044*
C110.63092 (16)1.35616 (11)0.27252 (9)0.0302 (2)
H11A0.73201.33230.29540.045*
H11B0.54351.28870.26770.045*
H11C0.61461.43390.32200.045*
C120.48046 (13)1.41540 (11)0.12999 (10)0.0281 (2)
H12A0.48691.43010.06310.042*
H12B0.46311.49280.17950.042*
H12C0.39181.34810.12310.042*
C130.75971 (11)1.03208 (8)0.23554 (7)0.01525 (17)
H13A0.68261.05490.28380.018*
H13B0.76071.09040.19270.018*
C140.92434 (11)1.05180 (9)0.29746 (7)0.01634 (17)
C151.11423 (11)1.22141 (9)0.42447 (7)0.01927 (19)
C161.13366 (13)1.15205 (11)0.50493 (8)0.0253 (2)
H16A1.04391.15920.54380.038*
H16B1.23331.18910.55190.038*
H16C1.13631.06310.47100.038*
C171.09683 (14)1.35762 (10)0.47396 (9)0.0297 (2)
H17A1.08661.40110.42100.045*
H17B1.19101.39940.52490.045*
H17C1.00171.36020.50790.045*
C181.24998 (13)1.21390 (12)0.36136 (8)0.0275 (2)
H18A1.23311.26000.31070.041*
H18B1.25361.12560.32570.041*
H18C1.35081.25130.40690.041*
N0.70429 (9)0.90458 (7)0.16899 (6)0.01390 (15)
O10.69273 (8)1.02472 (6)0.02395 (5)0.01726 (14)
O20.64089 (10)1.30065 (7)0.04679 (6)0.02538 (17)
O30.65294 (9)1.25075 (6)0.10336 (5)0.01911 (15)
O41.00875 (9)0.97290 (7)0.29456 (6)0.02586 (17)
O50.96028 (8)1.17262 (6)0.35625 (5)0.01879 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C190.0172 (4)0.0162 (4)0.0156 (4)0.0038 (3)0.0043 (3)0.0070 (3)
C200.0163 (4)0.0170 (4)0.0145 (4)0.0012 (3)0.0021 (3)0.0055 (3)
C210.0177 (4)0.0205 (5)0.0230 (5)0.0016 (3)0.0091 (4)0.0079 (4)
C220.0303 (5)0.0251 (5)0.0355 (6)0.0040 (4)0.0150 (5)0.0154 (5)
C230.0285 (5)0.0250 (5)0.0253 (5)0.0036 (4)0.0122 (4)0.0051 (4)
C240.0188 (5)0.0334 (6)0.0316 (6)0.0010 (4)0.0047 (4)0.0080 (5)
O60.0218 (3)0.0207 (3)0.0235 (3)0.0069 (3)0.0072 (3)0.0096 (3)
O70.0181 (3)0.0190 (3)0.0227 (3)0.0040 (3)0.0082 (3)0.0103 (3)
C10.0135 (4)0.0148 (4)0.0128 (4)0.0005 (3)0.0014 (3)0.0033 (3)
C20.0174 (4)0.0175 (4)0.0188 (4)0.0034 (3)0.0037 (3)0.0066 (3)
C30.0199 (4)0.0207 (5)0.0224 (5)0.0069 (4)0.0060 (4)0.0056 (4)
C40.0205 (4)0.0225 (5)0.0185 (4)0.0042 (4)0.0073 (4)0.0035 (4)
C50.0205 (4)0.0200 (4)0.0151 (4)0.0019 (4)0.0040 (3)0.0058 (3)
C60.0150 (4)0.0148 (4)0.0141 (4)0.0017 (3)0.0016 (3)0.0035 (3)
C70.0243 (5)0.0166 (4)0.0145 (4)0.0034 (3)0.0014 (3)0.0071 (3)
C80.0178 (4)0.0175 (4)0.0178 (4)0.0012 (3)0.0014 (3)0.0061 (3)
C90.0213 (4)0.0152 (4)0.0227 (5)0.0036 (3)0.0041 (4)0.0021 (3)
C100.0250 (5)0.0188 (5)0.0403 (6)0.0001 (4)0.0069 (5)0.0022 (4)
C110.0401 (6)0.0281 (6)0.0221 (5)0.0100 (5)0.0079 (5)0.0034 (4)
C120.0238 (5)0.0256 (5)0.0340 (6)0.0096 (4)0.0033 (4)0.0051 (4)
C130.0169 (4)0.0136 (4)0.0145 (4)0.0021 (3)0.0014 (3)0.0033 (3)
C140.0183 (4)0.0162 (4)0.0138 (4)0.0010 (3)0.0024 (3)0.0039 (3)
C150.0177 (4)0.0198 (4)0.0164 (4)0.0034 (3)0.0011 (3)0.0029 (3)
C160.0247 (5)0.0314 (6)0.0193 (5)0.0006 (4)0.0001 (4)0.0098 (4)
C170.0310 (6)0.0192 (5)0.0310 (6)0.0035 (4)0.0003 (5)0.0009 (4)
C180.0212 (5)0.0384 (6)0.0202 (5)0.0023 (4)0.0027 (4)0.0076 (4)
N0.0165 (3)0.0129 (3)0.0127 (3)0.0016 (3)0.0035 (3)0.0042 (3)
O10.0231 (3)0.0168 (3)0.0154 (3)0.0074 (3)0.0053 (3)0.0078 (2)
O20.0348 (4)0.0208 (4)0.0239 (4)0.0065 (3)0.0037 (3)0.0115 (3)
O30.0254 (4)0.0155 (3)0.0167 (3)0.0045 (3)0.0039 (3)0.0043 (2)
O40.0227 (4)0.0217 (4)0.0287 (4)0.0075 (3)0.0039 (3)0.0015 (3)
O50.0176 (3)0.0146 (3)0.0207 (3)0.0002 (2)0.0016 (3)0.0022 (3)
Geometric parameters (Å, º) top
C19—N1.4522 (12)C8—O21.2099 (12)
C19—C201.5209 (15)C8—O31.3334 (13)
C19—H19A0.9900C9—O31.4799 (13)
C19—H19B0.9900C9—C111.5197 (16)
C20—O61.2028 (13)C9—C121.5201 (17)
C20—O71.3471 (12)C9—C101.5221 (17)
C21—O71.4798 (14)C10—H10A0.9800
C21—C231.5214 (16)C10—H10B0.9800
C21—C241.5214 (18)C10—H10C0.9800
C21—C221.5235 (16)C11—H11A0.9800
C22—H22A0.9800C11—H11B0.9800
C22—H22B0.9800C11—H11C0.9800
C22—H22C0.9800C12—H12A0.9800
C23—H23A0.9800C12—H12B0.9800
C23—H23B0.9800C12—H12C0.9800
C23—H23C0.9800C13—N1.4547 (14)
C24—H24A0.9800C13—C141.5211 (16)
C24—H24B0.9800C13—H13A0.9900
C24—H24C0.9800C13—H13B0.9900
C1—C21.3902 (14)C14—O41.2014 (13)
C1—C61.4124 (13)C14—O51.3475 (13)
C1—N1.4225 (13)C15—O51.4776 (15)
C2—C31.3931 (15)C15—C181.5185 (16)
C2—H20.9500C15—C161.5187 (15)
C3—C41.3835 (15)C15—C171.5203 (16)
C3—H30.9500C16—H16A0.9800
C4—C51.3908 (15)C16—H16B0.9800
C4—H40.9500C16—H16C0.9800
C5—C61.3930 (14)C17—H17A0.9800
C5—H50.9500C17—H17B0.9800
C6—O11.3658 (12)C17—H17C0.9800
C7—O11.4210 (12)C18—H18A0.9800
C7—C81.5114 (15)C18—H18B0.9800
C7—H7A0.9900C18—H18C0.9800
C7—H7B0.9900
N—C19—C20112.82 (8)O3—C9—C12110.92 (9)
N—C19—H19A109.0C11—C9—C12110.99 (10)
C20—C19—H19A109.0O3—C9—C10109.54 (9)
N—C19—H19B109.0C11—C9—C10110.77 (10)
C20—C19—H19B109.0C12—C9—C10112.23 (10)
H19A—C19—H19B107.8C9—C10—H10A109.5
O6—C20—O7125.74 (9)C9—C10—H10B109.5
O6—C20—C19126.34 (9)H10A—C10—H10B109.5
O7—C20—C19107.92 (8)C9—C10—H10C109.5
O7—C21—C23110.52 (9)H10A—C10—H10C109.5
O7—C21—C24109.37 (9)H10B—C10—H10C109.5
C23—C21—C24112.85 (10)C9—C11—H11A109.5
O7—C21—C22102.30 (8)C9—C11—H11B109.5
C23—C21—C22110.30 (10)H11A—C11—H11B109.5
C24—C21—C22111.00 (10)C9—C11—H11C109.5
C21—C22—H22A109.5H11A—C11—H11C109.5
C21—C22—H22B109.5H11B—C11—H11C109.5
H22A—C22—H22B109.5C9—C12—H12A109.5
C21—C22—H22C109.5C9—C12—H12B109.5
H22A—C22—H22C109.5H12A—C12—H12B109.5
H22B—C22—H22C109.5C9—C12—H12C109.5
C21—C23—H23A109.5H12A—C12—H12C109.5
C21—C23—H23B109.5H12B—C12—H12C109.5
H23A—C23—H23B109.5N—C13—C14114.80 (8)
C21—C23—H23C109.5N—C13—H13A108.6
H23A—C23—H23C109.5C14—C13—H13A108.6
H23B—C23—H23C109.5N—C13—H13B108.6
C21—C24—H24A109.5C14—C13—H13B108.6
C21—C24—H24B109.5H13A—C13—H13B107.5
H24A—C24—H24B109.5O4—C14—O5125.48 (10)
C21—C24—H24C109.5O4—C14—C13125.76 (9)
H24A—C24—H24C109.5O5—C14—C13108.77 (9)
H24B—C24—H24C109.5O5—C15—C18110.15 (9)
C20—O7—C21120.50 (8)O5—C15—C16110.73 (8)
C2—C1—C6118.28 (8)C18—C15—C16112.08 (10)
C2—C1—N122.73 (8)O5—C15—C17101.82 (9)
C6—C1—N118.93 (8)C18—C15—C17110.84 (10)
C1—C2—C3121.50 (9)C16—C15—C17110.78 (9)
C1—C2—H2119.3C15—C16—H16A109.5
C3—C2—H2119.3C15—C16—H16B109.5
C4—C3—C2119.51 (9)H16A—C16—H16B109.5
C4—C3—H3120.2C15—C16—H16C109.5
C2—C3—H3120.2H16A—C16—H16C109.5
C3—C4—C5120.39 (9)H16B—C16—H16C109.5
C3—C4—H4119.8C15—C17—H17A109.5
C5—C4—H4119.8C15—C17—H17B109.5
C4—C5—C6120.04 (9)H17A—C17—H17B109.5
C4—C5—H5120.0C15—C17—H17C109.5
C6—C5—H5120.0H17A—C17—H17C109.5
O1—C6—C5124.32 (9)H17B—C17—H17C109.5
O1—C6—C1115.41 (8)C15—C18—H18A109.5
C5—C6—C1120.27 (9)C15—C18—H18B109.5
O1—C7—C8110.93 (8)H18A—C18—H18B109.5
O1—C7—H7A109.5C15—C18—H18C109.5
C8—C7—H7A109.5H18A—C18—H18C109.5
O1—C7—H7B109.5H18B—C18—H18C109.5
C8—C7—H7B109.5C1—N—C19115.62 (8)
H7A—C7—H7B108.0C1—N—C13116.30 (8)
O2—C8—O3126.22 (9)C19—N—C13115.53 (8)
O2—C8—C7120.74 (9)C6—O1—C7118.82 (7)
O3—C8—C7113.00 (8)C8—O3—C9121.20 (8)
O3—C9—C11101.93 (8)C14—O5—C15121.63 (8)
N—C19—C20—O63.38 (14)C2—C1—N—C1922.02 (12)
N—C19—C20—O7176.98 (8)C6—C1—N—C19155.27 (8)
O6—C20—O7—C216.10 (15)C2—C1—N—C13118.34 (10)
C19—C20—O7—C21174.26 (8)C6—C1—N—C1364.36 (11)
C23—C21—O7—C2063.18 (12)C20—C19—N—C1153.39 (8)
C24—C21—O7—C2061.65 (12)C20—C19—N—C1365.93 (11)
C22—C21—O7—C20179.39 (9)C14—C13—N—C169.12 (11)
C6—C1—C2—C31.08 (14)C14—C13—N—C1971.28 (10)
N—C1—C2—C3176.23 (9)C5—C6—O1—C72.47 (13)
C1—C2—C3—C41.17 (15)C1—C6—O1—C7177.21 (8)
C2—C3—C4—C50.51 (15)C8—C7—O1—C6155.47 (8)
C3—C4—C5—C60.20 (15)O2—C8—O3—C91.17 (15)
C4—C5—C6—O1179.94 (9)C7—C8—O3—C9176.84 (8)
C4—C5—C6—C10.29 (14)C11—C9—O3—C8177.23 (9)
C2—C1—C6—O1179.34 (8)C12—C9—O3—C859.02 (12)
N—C1—C6—O13.25 (12)C10—C9—O3—C865.41 (12)
C2—C1—C6—C50.35 (13)O4—C14—O5—C150.78 (14)
N—C1—C6—C5177.07 (8)C13—C14—O5—C15179.17 (7)
O1—C7—C8—O2178.77 (9)C18—C15—O5—C1463.16 (12)
O1—C7—C8—O33.10 (11)C16—C15—O5—C1461.38 (11)
N—C13—C14—O40.71 (14)C17—C15—O5—C14179.20 (8)
N—C13—C14—O5179.33 (7)
 

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