#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:29:29 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155448.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_7155448
loop_
_publ_author_name
'Esgulian, Mathieu'
'Belot, Vincent'
'Guillot, Régis'
'Deloisy, Sandrine'
'Aitken, David J.'
_publ_section_title
;
 Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid
 derivatives.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1453
_journal_page_last               1462
_journal_paper_doi               10.1039/c6ob02759h
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H13 N O7'
_chemical_formula_sum            'C10 H13 N O7'
_chemical_formula_weight         259.21
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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-2016/6
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.033(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0454(6)
_cell_length_b                   14.0347(14)
_cell_length_c                   7.1416(8)
_cell_measurement_reflns_used    6262
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.90
_cell_volume                     594.73(11)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20042
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.409
_diffrn_reflns_theta_min         2.903
_exptl_absorpt_coefficient_mu    0.124
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1675
_refine_ls_R_factor_gt           0.1101
_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)+(0.1462P)²+1.0323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2694
_refine_ls_wR_factor_ref         0.3029
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2242
_reflns_number_total             3515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob02759h2.cif
_cod_data_source_block           15a
_cod_depositor_comments
'Adding full bibliography for 7155448--7155450.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7155448
_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.
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.999
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
C1 C 0.4051(13) 0.5907(6) 0.4801(14) 0.0404(19) Uani 1 1 d . .
H1 H 0.277170 0.614425 0.537862 0.049 Uiso 1 1 calc R U
C2 C 0.4242(14) 0.6498(5) 0.3103(13) 0.0391(18) Uani 1 1 d . .
H2A H 0.362447 0.615277 0.190927 0.047 Uiso 1 1 calc R U
H2B H 0.341188 0.710568 0.311640 0.047 Uiso 1 1 calc R U
C3 C 0.7671(14) 0.6561(5) 0.5045(15) 0.044(2) Uani 1 1 d . .
C4 C 0.6514(14) 0.6012(5) 0.8105(13) 0.041(2) Uani 1 1 d . .
C5 C 0.8802(15) 0.6259(7) 0.9221(15) 0.051(2) Uani 1 1 d . .
H5A H 0.908187 0.694095 0.908800 0.077 Uiso 1 1 calc R U
H5B H 0.994889 0.589083 0.873481 0.077 Uiso 1 1 calc R U
H5C H 0.887075 0.610614 1.057013 0.077 Uiso 1 1 calc R U
C6 C 0.3734(12) 0.4853(5) 0.4344(11) 0.0313(15) Uani 1 1 d . .
H7 H 0.232349 0.476623 0.336850 0.038 Uiso 1 1 calc R U
C7 C 0.3554(12) 0.4270(5) 0.6113(12) 0.0335(16) Uani 1 1 d . .
C8 C 0.1012(16) 0.3800(7) 0.8003(15) 0.050(2) Uani 1 1 d . .
H00E H -0.055782 0.389729 0.813058 0.075 Uiso 1 1 calc R U
H00F H 0.201935 0.402577 0.915857 0.075 Uiso 1 1 calc R U
H00G H 0.127706 0.311989 0.782513 0.075 Uiso 1 1 calc R U
C9 C 0.5409(12) 0.3746(5) 0.2668(10) 0.0280(13) Uani 1 1 d . .
C10 C 0.7387(15) 0.3486(5) 0.1851(13) 0.0388(18) Uani 1 1 d . .
H10A H 0.722962 0.282813 0.138647 0.058 Uiso 1 1 calc R U
H10B H 0.875440 0.354340 0.283375 0.058 Uiso 1 1 calc R U
H10C H 0.749272 0.391513 0.078846 0.058 Uiso 1 1 calc R U
N N 0.6221(10) 0.6070(5) 0.6152(12) 0.046(2) Uani 1 1 d . .
O1 O 0.4950(13) 0.5766(5) 0.8773(11) 0.0564(18) Uani 1 1 d . .
O2 O 0.6617(10) 0.6674(5) 0.3249(10) 0.0508(17) Uani 1 1 d . .
O3 O 0.9602(12) 0.6751(5) 0.5586(12) 0.0612(19) Uani 1 1 d . .
O4 O 0.5042(8) 0.3804(4) 0.7036(8) 0.0329(11) Uani 1 1 d . .
O5 O 0.1441(7) 0.4317(3) 0.6400(7) 0.0273(10) Uani 1 1 d . .
O6 O 0.5641(9) 0.4604(4) 0.3507(8) 0.0351(12) Uani 1 1 d . .
O7 O 0.3783(12) 0.3247(5) 0.2645(10) 0.0539(18) 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 0.0033 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
N C1 C2 104.2(7)
N C1 C6 110.3(6)
C2 C1 C6 113.1(8)
N C1 H1 109.7
C2 C1 H1 109.7
C6 C1 H1 109.7
O2 C2 C1 105.5(7)
O2 C2 H2A 110.6
C1 C2 H2A 110.6
O2 C2 H2B 110.6
C1 C2 H2B 110.6
H2A C2 H2B 108.8
O3 C3 O2 123.2(9)
O3 C3 N 125.8(10)
O2 C3 N 110.6(7)
O1 C4 N 117.8(8)
O1 C4 C5 125.3(10)
N C4 C5 116.9(8)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O6 C6 C1 104.4(6)
O6 C6 C7 113.7(6)
C1 C6 C7 111.7(7)
O6 C6 H7 108.9
C1 C6 H7 108.9
C7 C6 H7 108.9
O4 C7 O5 125.5(7)
O4 C7 C6 125.5(7)
O5 C7 C6 108.8(6)
O5 C8 H00E 109.5
O5 C8 H00F 109.5
H00E C8 H00F 109.5
O5 C8 H00G 109.5
H00E C8 H00G 109.5
H00F C8 H00G 109.5
O7 C9 O6 122.9(7)
O7 C9 C10 125.0(7)
O6 C9 C10 112.1(6)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 N C3 127.1(7)
C4 N C1 125.0(7)
C3 N C1 105.5(8)
C3 O2 C2 109.7(6)
C7 O5 C8 115.3(6)
C9 O6 C6 112.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N 1.490(11)
C1 C2 1.492(12)
C1 C6 1.519(10)
C1 H1 1.0000
C2 O2 1.441(10)
C2 H2A 0.9900
C2 H2B 0.9900
C3 O3 1.188(12)
C3 O2 1.328(12)
C3 N 1.460(12)
C4 O1 1.189(11)
C4 N 1.375(13)
C4 C5 1.499(12)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 O6 1.440(8)
C6 C7 1.526(11)
C6 H7 1.0000
C7 O4 1.202(10)
C7 O5 1.333(8)
C8 O5 1.421(9)
C8 H00E 0.9800
C8 H00F 0.9800
C8 H00G 0.9800
C9 O7 1.204(9)
C9 O6 1.340(9)
C9 C10 1.473(10)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
