Bimetallic Aluminum(salen) Catalyzed Synthesis of Oxazolidinones from Epoxides and Isocyanates
Baronsky, Thilo; Beattie, Christopher; Harrington, Ross W.; Irfan, Reyhan; North, Michael; Osende, Javier G.; Young, Carl; ACS Catalysis 3 (2013) 790–; doi:10.1021/cs4001046

data_4507776
_publ_section_title
;
 Bimetallic Aluminum(salen) Catalyzed Synthesis of Oxazolidinones from
 Epoxides and Isocyanates
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              790
_journal_paper_doi               10.1021/cs4001046
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.089(9)
_cell_angle_beta                 75.857(9)
_cell_angle_gamma                68.462(9)
_cell_formula_units_Z            2
_cell_length_a                   6.5346(6)
_cell_length_b                   8.8030(9)
_cell_length_c                   10.4461(11)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4492
_cell_measurement_theta_min      3.1856
_cell_volume                     542.00(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'thick-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2069
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Wed Nov 09 15:15:48 2011'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.4990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1857
_reflns_number_gt                1864
_reflns_number_total             2069
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cs4001046_si_002.cif
_cod_data_source_block           mn39
_cod_original_cell_volume        542.00(9)
_cod_database_code               4507776
_computing_special_details
;
TITL mn39 in P-1
CELL 0.71073   6.5346   8.8030  10.4461  85.089  75.857  68.462
ZERR    2.00   0.0006   0.0009   0.0011   0.009   0.009   0.009
LATT  1
SFAC C H N O
UNIT 26 30 2 4
TEMP -123
 
L.S. 8
BOND $H
CONF
 
FMAP 2
PLAN 20
 
ACTA 50
 
OMIT -3 52
 
REM colourless slab
SIZE 0.40 0.20 0.10
 
REM EXTI    0.016349
WGHT    0.086600    0.499000
BASF   0.11489
FVAR      32.54700
O1    4    0.268772    0.824049    0.339748    11.00000    0.01930    0.02603 =
         0.02242    0.00135   -0.01013   -0.00861
O2    4    0.007738    0.798049    0.516665    11.00000    0.01441    0.03313 =
         0.03428   -0.00179   -0.00574   -0.01043
N     3    0.354461    0.799082    0.535719    11.00000    0.01411    0.02143 =
         0.01795   -0.00004   -0.00391   -0.00594
C1    1    0.467487    0.869668    0.323641    11.00000    0.02097    0.01981 =
         0.02081    0.00038   -0.00660   -0.00895
AFIX  13
H1A   2    0.415892    0.989990    0.338491    11.00000   -1.20000
AFIX   0
C2    1    0.618029    0.828990    0.186663    11.00000    0.03122    0.02841 =
         0.01809    0.00272   -0.00610   -0.01509
AFIX  23
H2A   2    0.723332    0.889277    0.170935    11.00000   -1.20000
H2B   2    0.523111    0.867169    0.121204    11.00000   -1.20000
AFIX   0
C3    1    0.754423    0.648102    0.164588    11.00000    0.02878    0.02920 =
         0.01879   -0.00381   -0.00206   -0.01418
AFIX  23
H3A   2    0.862836    0.631142    0.077649    11.00000   -1.20000
H3B   2    0.651926    0.588684    0.164431    11.00000   -1.20000
AFIX   0
C4    1    0.882249    0.581289    0.273001    11.00000    0.01831    0.02653 =
         0.02646   -0.00583   -0.00052   -0.00651
AFIX  23
H4A   2    0.984861    0.640572    0.273278    11.00000   -1.20000
H4B   2    0.974911    0.464223    0.256292    11.00000   -1.20000
AFIX   0
C5    1    0.715297    0.601668    0.406371    11.00000    0.01603    0.02145 =
         0.02020    0.00067   -0.00437   -0.00479
AFIX  23
H5A   2    0.799701    0.556059    0.476128    11.00000   -1.20000
H5B   2    0.616716    0.539057    0.406220    11.00000   -1.20000
AFIX   0
C6    1    0.568647    0.780417    0.438264    11.00000    0.01497    0.02081 =
         0.01718   -0.00185   -0.00220   -0.00920
AFIX  13
H6A   2    0.654381    0.838861    0.468090    11.00000   -1.20000
AFIX   0
C7    1    0.190963    0.806634    0.471318    11.00000    0.01658    0.01796 =
         0.02325   -0.00105   -0.00601   -0.00443
C8    1    0.332500    0.783191    0.673961    11.00000    0.01868    0.01795 =
         0.01843   -0.00042   -0.00381   -0.00844
C9    1    0.523540    0.718075    0.725523    11.00000    0.01901    0.02704 =
         0.02082   -0.00098   -0.00436   -0.00642
AFIX  43
H9A   2    0.669389    0.682917    0.667770    11.00000   -1.20000
AFIX   0
C10   1    0.502336    0.704094    0.861317    11.00000    0.02975    0.03472 =
         0.02331    0.00049   -0.01133   -0.00922
AFIX  43
H10A  2    0.634178    0.659090    0.895526    11.00000   -1.20000
AFIX   0
C11   1    0.292121    0.754787    0.947045    11.00000    0.04128    0.03598 =
         0.01702    0.00064   -0.00478   -0.01929
AFIX  43
H11A  2    0.278032    0.743325    1.039725    11.00000   -1.20000
AFIX   0
C12   1    0.101811    0.822802    0.895231    11.00000    0.02898    0.03130 =
         0.02474   -0.00469    0.00473   -0.01429
AFIX  43
H12A  2   -0.043500    0.859597    0.953496    11.00000   -1.20000
AFIX   0
C13   1    0.119323    0.838112    0.760604    11.00000    0.01851    0.02429 =
         0.02428   -0.00086   -0.00200   -0.00581
AFIX  43
H13A  2   -0.012886    0.885751    0.726996    11.00000   -1.20000
 
HKLF 5
 
REM  mn39 in P-1
REM R1 =  0.0545 for   1864 Fo > 4sig(Fo)  and  0.0597 for all   2069 data
REM    146 parameters refined using      0 restraints
 
END  
     
WGHT      0.0866      0.4989 
REM Highest difference peak  0.300,  deepest hole -0.251,  1-sigma level  0.059
Q1    1   0.7849  0.8044  0.5331  11.00000  0.05    0.30
Q2    1   0.4979  0.6002  0.3966  11.00000  0.05    0.23
Q3    1   0.5324  0.8101  0.3752  11.00000  0.05    0.23
Q4    1   0.7921  0.6013  0.3400  11.00000  0.05    0.23
Q5    1   0.7169  0.7992  0.6255  11.00000  0.05    0.22
Q6    1   0.0323  0.6769  0.8612  11.00000  0.05    0.21
Q7    1   0.6295  0.6882  0.4212  11.00000  0.05    0.21
Q8    1   0.1724  0.6634  0.7672  11.00000  0.05    0.20
Q9    1   0.6409  0.8254  0.7758  11.00000  0.05    0.20
Q10   1   0.3425  0.6237  0.6938  11.00000  0.05    0.20
Q11   1  -0.0905  0.7830  0.6037  11.00000  0.05    0.20
Q12   1   0.5061  0.7520  0.8068  11.00000  0.05    0.19
Q13   1  -0.1249  0.7976  0.6401  11.00000  0.05    0.19
Q14   1   0.0282  0.8345  0.3198  11.00000  0.05    0.19
Q15   1   0.5820  0.7954  0.5375  11.00000  0.05    0.19
Q16   1   0.5599  0.8285  0.2588  11.00000  0.05    0.19
Q17   1   0.3882  0.7898  0.9028  11.00000  0.05    0.18
Q18   1  -0.0877  0.8198  0.4534  11.00000  0.05    0.18
Q19   1   0.3145  0.7181  0.5110  11.00000  0.05    0.18
Q20   1   0.0941  0.7064  0.5037  11.00000  0.05    0.18
;