#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/60/7206038.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7206038
loop_
_publ_author_name
'Czarnecki, Paweł'
'Plutecka, Agnieszka'
'Gawroński, Jacek'
'Kacprzak, Karol'
_publ_section_title
;
 Simple and practical direct asymmetric aldol reaction of
 hydroxyacetone catalyzed by 9-amino Cinchona alkaloid tartrates
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              1280
_journal_paper_doi               10.1039/c1gc15064b
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_chemical_name_common
syn-(3S,4R)-3,4-dihydroxy-4-(4-nitrophenyl)butan-2-one
_chemical_name_systematic
;
syn-(3S,4R)-3,4-dihydroxy-
4-(4-nitrophenyl)butan-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6835(4)
_cell_length_b                   9.2616(8)
_cell_length_c                   23.4038(16)
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      76.63
_cell_measurement_theta_min      3.78
_cell_volume                     1015.18(14)
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_molecular_graphics    'ORTEP3 for Windows, 1997'
_computing_publication_material  'PLATON, 1998'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_detector_area_resol_mean 5.2679
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0074
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7684
_diffrn_reflns_theta_full        76.63
_diffrn_reflns_theta_max         76.63
_diffrn_reflns_theta_min         3.78
_diffrn_standards_interval_count 4
_diffrn_standards_interval_time  60
_diffrn_standards_number         7733
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.2449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2053
_reflns_number_total             2060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1gc15064b.txt
_cod_data_source_block           syn_5
_cod_original_cell_volume        1015.19(15)
_cod_database_code               7206038
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'
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_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'
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_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_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) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26946047
