# Supplementary Material (ESI) for Green Chemistry
# This journal is (c) The Royal Society of Chemistry 2011
data_global
_journal_name_full 'Green Chemistry'
_journal_coden_cambridge 1048
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_name
_publ_author_address
'Pawe\/l Czarnecki'
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
'Agnieszka Plutecka'
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
J.Gawronski
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
'Karol Kacprzak'
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
_publ_contact_author_address
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
_publ_contact_author_email karol.kacprzak@gmail.com
#TrackingRef '- syn_5.CIF'
_publ_contact_author_name 'Karol Kacprzak'
_publ_requested_category CO
_publ_section_title
;
Green and Practical Direct Asymmetric
Aldol Reaction of Hydroxyacetone Catalyzed
by 9-Amino Cinchona Alkaloid Tartrates.
;
data_syn_5
_database_code_depnum_ccdc_archive 'CCDC 783759'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
syn-(3S,4R)-3,4-dihydroxy-
4-(4-nitrophenyl)butan-2-one
;
_chemical_name_common
syn-(3S,4R)-3,4-dihydroxy-4-(4-nitrophenyl)butan-2-one
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H11 N O5'
_chemical_formula_sum 'C10 H11 N O5'
_chemical_formula_weight 225.20
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 4.6835(4)
_cell_length_b 9.2616(8)
_cell_length_c 23.4038(16)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1015.19(15)
_cell_formula_units_Z 4
_cell_measurement_temperature 130.0(1)
_cell_measurement_reflns_used 6608
_cell_measurement_theta_min 3.78
_cell_measurement_theta_max 76.63
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.473
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 472
_exptl_absorpt_coefficient_mu 1.024
_exptl_absorpt_correction_T_min 0.833
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature 130.0(1)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 5.2679
_diffrn_standards_number 7733
_diffrn_standards_interval_count 4
_diffrn_standards_interval_time 60
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7684
_diffrn_reflns_av_R_equivalents 0.0135
_diffrn_reflns_av_sigmaI/netI 0.0074
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 3.78
_diffrn_reflns_theta_max 76.63
_reflns_number_total 2060
_reflns_number_gt 2053
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP3 for Windows, 1997'
_computing_publication_material 'PLATON, 1998'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.2449P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.09(16)
_refine_ls_number_reflns 2060
_refine_ls_number_parameters 178
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0257
_refine_ls_R_factor_gt 0.0256
_refine_ls_wR_factor_ref 0.0688
_refine_ls_wR_factor_gt 0.0687
_refine_ls_goodness_of_fit_ref 1.088
_refine_ls_restrained_S_all 1.088
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6904(4) 0.51767(17) 0.40540(5) 0.0385(4) Uani 1 1 d . . .
H1C H 0.6742 0.6210 0.4066 0.058 Uiso 1 1 calc R . .
H1B H 0.5656 0.4801 0.3765 0.058 Uiso 1 1 calc R . .
H1A H 0.8839 0.4914 0.3967 0.058 Uiso 1 1 calc R . .
C2 C 0.6089(3) 0.45617(13) 0.46213(5) 0.0209(3) Uani 1 1 d . . .
O2 O 0.41002(19) 0.37303(10) 0.46836(4) 0.0277(2) Uani 1 1 d . . .
C3 C 0.7982(2) 0.49305(12) 0.51339(5) 0.0175(2) Uani 1 1 d . . .
H3 H 0.930(3) 0.4128(16) 0.5164(6) 0.021(3) Uiso 1 1 d . . .
O3 O 0.94423(18) 0.62558(9) 0.50392(3) 0.02027(18) Uani 1 1 d . . .
H3O H 1.101(4) 0.6177(18) 0.5222(7) 0.029(4) Uiso 1 1 d . . .
C4 C 0.6206(2) 0.50306(12) 0.56840(4) 0.0181(2) Uani 1 1 d . . .
H4 H 0.503(3) 0.4136(16) 0.5693(6) 0.027(4) Uiso 1 1 d . . .
O4 O 0.43440(17) 0.62493(9) 0.56524(3) 0.02069(18) Uani 1 1 d . . .
H4O H 0.524(4) 0.6932(19) 0.5491(7) 0.038(5) Uiso 1 1 d . . .
C5 C 0.8102(3) 0.50835(12) 0.62078(5) 0.0179(2) Uani 1 1 d . . .
C6 C 0.8334(3) 0.63208(13) 0.65442(5) 0.0212(2) Uani 1 1 d . . .
H6 H 0.728(3) 0.7167(16) 0.6456(6) 0.020(3) Uiso 1 1 d . . .
C7 C 1.0149(3) 0.63413(13) 0.70124(5) 0.0228(2) Uani 1 1 d . . .
H7 H 1.034(4) 0.7229(17) 0.7246(6) 0.033(4) Uiso 1 1 d . . .
C8 C 1.1701(3) 0.51105(13) 0.71380(5) 0.0203(2) Uani 1 1 d . . .
C9 C 1.1525(3) 0.38616(13) 0.68132(5) 0.0213(2) Uani 1 1 d . . .
H9 H 1.263(3) 0.3010(17) 0.6914(6) 0.026(4) Uiso 1 1 d . . .
C10 C 0.9688(3) 0.38597(13) 0.63493(5) 0.0208(2) Uani 1 1 d . . .
H10 H 0.941(4) 0.3012(17) 0.6128(6) 0.027(4) Uiso 1 1 d . . .
N1 N 1.3571(2) 0.51137(12) 0.76425(4) 0.0246(2) Uani 1 1 d . . .
O5 O 1.5102(2) 0.40654(11) 0.77253(4) 0.0395(3) Uani 1 1 d . . .
O6 O 1.3483(2) 0.61638(11) 0.79611(4) 0.0377(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0531(10) 0.0424(8) 0.0199(6) 0.0012(6) -0.0070(6) -0.0172(8)
C2 0.0209(6) 0.0214(5) 0.0203(5) -0.0053(4) -0.0012(5) 0.0021(5)
O2 0.0241(5) 0.0315(5) 0.0274(4) -0.0076(4) 0.0002(4) -0.0058(4)
C3 0.0156(5) 0.0178(5) 0.0190(5) 0.0007(4) 0.0001(4) 0.0004(5)
O3 0.0164(4) 0.0223(4) 0.0221(4) 0.0040(3) -0.0025(3) -0.0037(3)
C4 0.0167(5) 0.0193(5) 0.0183(5) 0.0001(4) 0.0006(4) -0.0003(5)
O4 0.0167(4) 0.0226(4) 0.0228(4) 0.0003(3) 0.0001(3) 0.0013(4)
C5 0.0161(5) 0.0209(5) 0.0166(5) 0.0018(4) 0.0029(4) -0.0022(5)
C6 0.0220(6) 0.0197(5) 0.0218(5) -0.0002(4) 0.0006(4) 0.0021(5)
C7 0.0248(6) 0.0228(5) 0.0209(5) -0.0034(5) 0.0008(5) -0.0012(5)
C8 0.0194(6) 0.0259(6) 0.0157(5) 0.0015(4) 0.0002(4) -0.0030(5)
C9 0.0226(6) 0.0216(5) 0.0198(5) 0.0037(4) 0.0009(4) 0.0020(5)
C10 0.0253(6) 0.0187(5) 0.0184(5) -0.0008(4) 0.0006(5) 0.0001(5)
N1 0.0259(5) 0.0283(5) 0.0197(5) 0.0027(4) -0.0023(4) -0.0042(5)
O5 0.0452(6) 0.0399(6) 0.0334(5) -0.0006(4) -0.0179(5) 0.0109(5)
O6 0.0491(6) 0.0357(5) 0.0283(5) -0.0082(4) -0.0146(4) -0.0012(5)
_geom_special_details
;
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.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4944(17) . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1A 0.9600 . ?
C2 O2 1.2174(15) . ?
C2 C3 1.5302(15) . ?
C3 O3 1.4225(14) . ?
C3 C4 1.5356(15) . ?
C3 H3 0.968(16) . ?
O3 H3O 0.854(18) . ?
C4 O4 1.4283(14) . ?
C4 C5 1.5144(15) . ?
C4 H4 0.995(16) . ?
O4 H4O 0.847(19) . ?
C5 C6 1.3946(16) . ?
C5 C10 1.3950(16) . ?
C6 C7 1.3871(16) . ?
C6 H6 0.948(15) . ?
C7 C8 1.3833(16) . ?
C7 H7 0.992(16) . ?
C8 C9 1.3866(17) . ?
C8 N1 1.4702(15) . ?
C9 C10 1.3854(16) . ?
C9 H9 0.973(16) . ?
C10 H10 0.950(16) . ?
N1 O5 1.2223(15) . ?
N1 O6 1.2262(14) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
O2 C2 C1 122.88(11) . . ?
O2 C2 C3 119.38(10) . . ?
C1 C2 C3 117.62(11) . . ?
O3 C3 C2 110.42(9) . . ?
O3 C3 C4 109.81(9) . . ?
C2 C3 C4 110.91(9) . . ?
O3 C3 H3 111.5(9) . . ?
C2 C3 H3 104.7(8) . . ?
C4 C3 H3 109.3(8) . . ?
C3 O3 H3O 105.2(11) . . ?
O4 C4 C5 111.99(9) . . ?
O4 C4 C3 109.57(9) . . ?
C5 C4 C3 111.28(9) . . ?
O4 C4 H4 108.8(9) . . ?
C5 C4 H4 109.5(9) . . ?
C3 C4 H4 105.5(9) . . ?
C4 O4 H4O 108.1(13) . . ?
C6 C5 C10 119.47(11) . . ?
C6 C5 C4 121.96(10) . . ?
C10 C5 C4 118.56(10) . . ?
C7 C6 C5 120.34(11) . . ?
C7 C6 H6 118.6(9) . . ?
C5 C6 H6 121.1(9) . . ?
C8 C7 C6 118.59(11) . . ?
C8 C7 H7 121.2(10) . . ?
C6 C7 H7 120.2(10) . . ?
C7 C8 C9 122.67(11) . . ?
C7 C8 N1 118.82(10) . . ?
C9 C8 N1 118.50(10) . . ?
C10 C9 C8 117.87(11) . . ?
C10 C9 H9 121.3(9) . . ?
C8 C9 H9 120.8(9) . . ?
C9 C10 C5 121.05(11) . . ?
C9 C10 H10 120.9(9) . . ?
C5 C10 H10 118.0(10) . . ?
O5 N1 O6 123.60(10) . . ?
O5 N1 C8 118.38(10) . . ?
O6 N1 C8 118.02(10) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 O3 -158.76(10) . . . . ?
C1 C2 C3 O3 25.11(15) . . . . ?
O2 C2 C3 C4 -36.79(14) . . . . ?
C1 C2 C3 C4 147.08(11) . . . . ?
O3 C3 C4 O4 54.87(12) . . . . ?
C2 C3 C4 O4 -67.45(11) . . . . ?
O3 C3 C4 C5 -69.52(11) . . . . ?
C2 C3 C4 C5 168.15(9) . . . . ?
O4 C4 C5 C6 -11.62(15) . . . . ?
C3 C4 C5 C6 111.40(12) . . . . ?
O4 C4 C5 C10 169.38(10) . . . . ?
C3 C4 C5 C10 -67.59(13) . . . . ?
C10 C5 C6 C7 0.66(18) . . . . ?
C4 C5 C6 C7 -178.32(11) . . . . ?
C5 C6 C7 C8 -0.31(17) . . . . ?
C6 C7 C8 C9 0.35(18) . . . . ?
C6 C7 C8 N1 -178.44(11) . . . . ?
C7 C8 C9 C10 -0.72(18) . . . . ?
N1 C8 C9 C10 178.07(10) . . . . ?
C8 C9 C10 C5 1.07(17) . . . . ?
C6 C5 C10 C9 -1.06(18) . . . . ?
C4 C5 C10 C9 177.96(11) . . . . ?
C7 C8 N1 O5 -174.35(11) . . . . ?
C9 C8 N1 O5 6.81(17) . . . . ?
C7 C8 N1 O6 6.51(17) . . . . ?
C9 C8 N1 O6 -172.32(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 76.63
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.215
_refine_diff_density_min -0.133
_refine_diff_density_rms 0.033