#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:53:46 +0100 (mar 22 de mar de 2016) $
#$Revision: 178981 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/04/4120463.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_4120463
loop_
_publ_author_name
'Aydillo, Carlos'
'Compañón, Ismael'
'Avenoza, Alberto'
'Busto, Jesús H'
'Corzana, Francisco'
'Peregrina, Jesús M'
'Zurbano, María M'
_publ_section_title
;
 S-Michael additions to chiral dehydroalanines as an entry to glycosylated
 cysteines and a sulfa-tn antigen mimic.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              789
_journal_page_last               800
_journal_paper_doi               10.1021/ja411522f
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C9 H13 N O6'
_chemical_formula_sum            'C9 H13 N O6'
_chemical_formula_weight         231.20
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 94.28
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.801
_cell_length_b                   11.467
_cell_length_c                   6.882
_cell_measurement_temperature    193(2)
_cell_volume                     535.210
_computing_cell_refinement       'Denzo and Scalepak (1997)'
_computing_data_collection       'Nonius Kappa CCD'
_computing_data_reduction        'Denzo and Scalepak (1997)'
_computing_molecular_graphics    'ORTEP III'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8415
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       0.047(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0342
_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/[σ²(Fo²)+(0.1059P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2264
_reflns_number_total             2413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411522f_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        535.2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4120463
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O 0.63464(15) 0.11035(9) 0.81325(16) 0.0236(3) Uani 1 1 d .
O2 O 0.5832(2) 0.30717(14) 0.33722(16) 0.0384(3) Uani 1 1 d .
O6 O 0.35360(18) 0.42908(11) 0.9378(2) 0.0344(3) Uani 1 1 d .
H6 H 0.3565 0.4859 1.0102 0.052 Uiso 1 1 calc R
O3 O 0.78324(18) 0.15636(11) 0.41536(16) 0.0296(3) Uani 1 1 d .
O4 O 1.08647(16) 0.15436(12) 0.58728(16) 0.0295(3) Uani 1 1 d .
N1 N 0.70497(18) 0.27736(10) 0.65669(16) 0.0205(3) Uani 1 1 d .
O5 O 0.67656(19) 0.46803(11) 0.92045(19) 0.0371(3) Uani 1 1 d .
C2 C 0.8952(2) 0.11276(14) 0.5897(2) 0.0229(3) Uani 1 1 d .
C3 C 0.7997(2) 0.17722(12) 0.7561(2) 0.0198(3) Uani 1 1 d .
C4 C 0.5232(2) 0.30314(13) 0.7486(2) 0.0211(3) Uani 1 1 d .
H4 H 0.4143 0.3114 0.6479 0.025 Uiso 1 1 calc R
C5 C 1.2003(3) 0.1056(2) 0.4385(3) 0.0396(5) Uani 1 1 d .
H5A H 1.3297 0.1396 0.4478 0.059 Uiso 1 1 calc R
H5B H 1.1361 0.1221 0.3125 0.059 Uiso 1 1 calc R
H5C H 1.2108 0.0227 0.4561 0.059 Uiso 1 1 calc R
C6 C 0.6814(2) 0.25218(15) 0.4581(2) 0.0262(3) Uani 1 1 d .
C7 C 0.4898(2) 0.19226(13) 0.8726(2) 0.0219(3) Uani 1 1 d .
H7A H 0.5103 0.2092 1.0107 0.026 Uiso 1 1 calc R
H7B H 0.3574 0.1621 0.8453 0.026 Uiso 1 1 calc R
C8 C 0.5331(3) 0.41071(13) 0.8775(2) 0.0251(3) Uani 1 1 d .
C9 C 0.9382(2) 0.20900(17) 0.9309(2) 0.0292(4) Uani 1 1 d .
H9A H 1.0468 0.2534 0.8886 0.044 Uiso 1 1 calc R
H9B H 0.9870 0.1391 0.9943 0.044 Uiso 1 1 calc R
H9C H 0.8685 0.2546 1.0204 0.044 Uiso 1 1 calc R
C10 C 0.8782(3) -0.01900(16) 0.5941(3) 0.0373(4) Uani 1 1 d .
H10A H 0.7420 -0.0407 0.5958 0.056 Uiso 1 1 calc R
H10B H 0.9504 -0.0486 0.7088 0.056 Uiso 1 1 calc R
H10C H 0.9314 -0.0512 0.4804 0.056 Uiso 1 1 calc R
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
O1 0.0228(5) 0.0203(5) 0.0288(6) 0.0022(4) 0.0089(4) -0.0004(4)
O2 0.0452(7) 0.0506(8) 0.0196(5) 0.0070(5) 0.0034(5) 0.0083(6)
O6 0.0329(6) 0.0305(6) 0.0411(7) -0.0156(5) 0.0123(5) -0.0001(5)
O3 0.0316(6) 0.0389(6) 0.0183(5) -0.0079(5) 0.0013(4) 0.0044(5)
O4 0.0217(5) 0.0404(6) 0.0275(6) -0.0121(5) 0.0081(4) -0.0032(5)
N1 0.0252(6) 0.0207(6) 0.0162(6) -0.0001(4) 0.0054(4) -0.0003(5)
O5 0.0417(7) 0.0300(7) 0.0420(7) -0.0135(5) 0.0190(6) -0.0120(5)
C2 0.0219(6) 0.0269(7) 0.0203(7) -0.0055(6) 0.0036(5) 0.0000(6)
C3 0.0197(6) 0.0220(7) 0.0181(6) 0.0001(5) 0.0044(5) -0.0025(5)
C4 0.0236(7) 0.0207(6) 0.0194(6) 0.0000(5) 0.0040(5) 0.0012(5)
C5 0.0280(8) 0.0584(12) 0.0343(9) -0.0167(8) 0.0141(7) -0.0024(8)
C6 0.0278(7) 0.0320(8) 0.0194(7) -0.0005(6) 0.0056(5) -0.0012(6)
C7 0.0217(7) 0.0228(6) 0.0220(7) 0.0019(5) 0.0066(5) 0.0006(5)
C8 0.0339(8) 0.0197(7) 0.0229(7) 0.0011(5) 0.0098(6) 0.0001(5)
C9 0.0235(7) 0.0444(9) 0.0195(7) -0.0051(6) 0.0006(5) 0.0007(6)
C10 0.0442(9) 0.0252(8) 0.0443(10) -0.0090(7) 0.0156(8) 0.0004(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C3 O1 C7 107.08(11)
C6 O3 C2 110.25(11)
C2 O4 C5 115.39(13)
C6 N1 C4 115.30(11)
C6 N1 C3 108.10(12)
C4 N1 C3 108.31(11)
O4 C2 O3 107.73(13)
O4 C2 C10 114.60(14)
O3 C2 C10 108.78(14)
O4 C2 C3 106.90(11)
O3 C2 C3 102.86(11)
C10 C2 C3 115.13(13)
O1 C3 N1 102.78(11)
O1 C3 C9 111.26(12)
N1 C3 C9 114.12(12)
O1 C3 C2 109.10(11)
N1 C3 C2 102.92(11)
C9 C3 C2 115.60(12)
N1 C4 C8 114.56(12)
N1 C4 C7 103.58(11)
C8 C4 C7 110.18(11)
O2 C6 O3 123.05(15)
O2 C6 N1 125.83(15)
O3 C6 N1 111.13(13)
O1 C7 C4 104.24(11)
O5 C8 O6 125.79(15)
O5 C8 C4 126.25(15)
O6 C8 C4 107.95(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4383(16)
O1 C7 1.4421(17)
O2 C6 1.205(2)
O6 C8 1.335(2)
O3 C6 1.343(2)
O3 C2 1.4604(18)
O4 C2 1.3866(18)
O4 C5 1.442(2)
N1 C6 1.3945(19)
N1 C4 1.4602(19)
N1 C3 1.4614(18)
O5 C8 1.195(2)
C2 C10 1.516(2)
C2 C3 1.547(2)
C3 C9 1.516(2)
C4 C8 1.518(2)
C4 C7 1.557(2)
