#------------------------------------------------------------------------------
#$Date: 2016-08-05 06:38:56 +0300 (Fri, 05 Aug 2016) $
#$Revision: 184967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/33/1543389.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_1543389
loop_
_publ_author_name
'Gutiérrez-Jiménez, Marta I'
'Aydillo, Carlos'
'Navo, Claudio D.'
'Avenoza, Alberto'
'Corzana, Francisco'
'Jiménez-Osés, Gonzalo'
'Zurbano, María M'
'Busto, Jesús H'
'Peregrina, Jesús M'
_publ_section_title
;
 Bifunctional Chiral Dehydroalanines for Peptide Coupling and
 Stereoselective S-Michael Addition.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2796
_journal_page_last               2799
_journal_paper_doi               10.1021/acs.orglett.6b00840
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H11 N O5'
_chemical_formula_sum            'C9 H11 N O5'
_chemical_formula_weight         213.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.5600(51)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   8.01630(70)
_cell_length_b                   5.94090(59)
_cell_length_c                   10.63000(100)
_cell_measurement_reflns_used    364
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      2.68
_cell_volume                     479.91(8)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4110
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.838
_diffrn_source                   'normal-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                1935
_reflns_number_total             2151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b00840_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1543389--1543390.cif.'
_cod_original_cell_volume        479.914(79)
_cod_database_code               1543389
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.4511(2) 0.2409(3) -0.05629(17) 0.0311(4) Uani 1 1 d . .
O2 O 0.7763(2) 0.4899(3) 0.31944(16) 0.0297(4) Uani 1 1 d . .
O5 O 0.4347(2) 0.1358(3) 0.34236(18) 0.0326(4) Uani 1 1 d . .
O3 O 0.3843(2) 0.2825(3) 0.13250(16) 0.0298(4) Uani 1 1 d . .
N1 N 0.6673(2) 0.2383(4) 0.14890(19) 0.0270(4) Uani 1 1 d . .
O4 O 0.9836(2) 0.6601(3) 0.2513(2) 0.0402(5) Uani 1 1 d . .
C1 C 0.4967(3) 0.2535(4) 0.0629(2) 0.0264(5) Uani 1 1 d . .
C2 C 0.2541(3) 0.1231(5) 0.3368(3) 0.0383(6) Uani 1 1 d . .
H2A H 0.2287 0.2430 0.3884 0.057 Uiso 1 1 calc R U
H2B H 0.2327 -0.0189 0.3718 0.057 Uiso 1 1 calc R U
H2C H 0.1799 0.1368 0.2463 0.057 Uiso 1 1 calc R U
C3 C 0.4777(3) 0.3143(4) 0.2743(2) 0.0267(5) Uani 1 1 d . .
C4 C 0.4302(3) 0.5435(5) 0.3126(3) 0.0317(5) Uani 1 1 d . .
H4A H 0.3046 0.5559 0.2890 0.047 Uiso 1 1 calc R U
H4B H 0.4736 0.6568 0.2666 0.047 Uiso 1 1 calc R U
H4C H 0.4822 0.5640 0.4066 0.047 Uiso 1 1 calc R U
C5 C 0.8706(3) 0.5196(4) 0.2338(3) 0.0300(5) Uani 1 1 d . .
C6 C 0.8066(3) 0.3551(4) 0.1230(3) 0.0288(5) Uani 1 1 d . .
C7 C 0.6757(3) 0.2822(4) 0.2850(2) 0.0264(5) Uani 1 1 d . .
C8 C 0.8636(3) 0.3345(5) 0.0200(3) 0.0388(6) Uani 1 1 d . .
H8A H 0.8075(14) 0.228(3) -0.0504(18) 0.047 Uiso 1 1 calc R U
H8B H 0.962(3) 0.426(2) 0.0143(3) 0.047 Uiso 1 1 calc R U
C9 C 0.7747(3) 0.1016(5) 0.3797(3) 0.0346(6) Uani 1 1 d . .
H9A H 0.8905 0.0854 0.3724 0.052 Uiso 1 1 calc R U
H9B H 0.7127 -0.0386 0.3580 0.052 Uiso 1 1 calc R U
H9C H 0.7840 0.1434 0.4689 0.052 Uiso 1 1 calc R U
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
C5 O2 C7 108.78(18)
C3 O5 C2 115.71(19)
C1 O3 C3 111.71(17)
C1 N1 C6 121.0(2)
C1 N1 C7 111.66(19)
C6 N1 C7 108.46(19)
O1 C1 O3 123.7(2)
O1 C1 N1 126.5(2)
O3 C1 N1 109.79(19)
O5 C3 O3 107.88(18)
O5 C3 C4 115.15(19)
O3 C3 C4 107.75(19)
O5 C3 C7 106.44(19)
O3 C3 C7 103.44(18)
C4 C3 C7 115.4(2)
O4 C5 O2 122.4(2)
O4 C5 C6 129.1(2)
O2 C5 C6 108.5(2)
C8 C6 N1 128.3(3)
C8 C6 C5 126.4(2)
N1 C6 C5 105.2(2)
N1 C7 O2 104.44(18)
N1 C7 C9 112.6(2)
O2 C7 C9 107.61(19)
N1 C7 C3 103.02(18)
O2 C7 C3 112.50(18)
C9 C7 C3 116.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.204(3)
O2 C5 1.367(3)
O2 C7 1.456(3)
O5 C3 1.388(3)
O5 C2 1.431(3)
O3 C1 1.346(3)
O3 C3 1.466(3)
N1 C1 1.385(3)
N1 C6 1.415(3)
N1 C7 1.451(3)
O4 C5 1.202(3)
C3 C4 1.504(4)
C3 C7 1.567(3)
C5 C6 1.490(4)
C6 C8 1.320(4)
C7 C9 1.512(3)
