#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154426.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_7154426
loop_
_publ_author_name
'de la Fuente, Alex'
'Mena-Barragán, Teresa'
'Farrar-Tobar, Ronald A'
'Verdaguer, Xavier'
'García Fernández, José M'
'Ortiz Mellet, Carmen'
'Riera, Antoni'
_publ_section_title
;
 Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc)
 and ureido-DNJNAc derivatives as new hexosaminidase inhibitors.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6500
_journal_page_last               6510
_journal_paper_doi               10.1039/c5ob00507h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H16 N4 O4'
_chemical_formula_weight         304.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6858(9)
_cell_length_b                   9.9838(6)
_cell_length_c                   15.1087(10)
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.88
_cell_measurement_theta_min      2.45
_cell_volume                     1461.03(19)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9047
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.581
_diffrn_reflns_theta_min         2.445
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0576
_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)+(0.0835P)²+0.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                4142
_reflns_number_total             4568
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob00507h2.cif
_cod_data_source_block           mo_AFC561_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154425--7154426.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154426
#BEGIN Tags that were not found in dictionaries:
_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   0.997
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.9114(3) 1.0986(2) 0.11576(15) 0.0216(4) Uani 1 1 d . .
C2 C 0.7035(3) 0.9969(2) 0.08700(17) 0.0232(5) Uani 1 1 d . .
H2A H 0.6591 1.0184 0.0297 0.028 Uiso 1 1 calc R U
H2B H 0.6322 0.9633 0.1284 0.028 Uiso 1 1 calc R U
C3 C 0.8186(2) 0.8928(2) 0.07451(14) 0.0176(4) Uani 1 1 d . .
H3 H 0.8128 0.8516 0.0143 0.021 Uiso 1 1 calc R U
C4 C 0.8219(2) 0.78372(18) 0.14594(14) 0.0161(4) Uani 1 1 d . .
H4 H 0.8043 0.8255 0.2050 0.019 Uiso 1 1 calc R U
C5 C 0.9626(2) 0.7129(2) 0.14760(15) 0.0190(4) Uani 1 1 d . .
H5 H 0.9643 0.6447 0.1961 0.023 Uiso 1 1 calc R U
C6 C 1.0804(2) 0.8153(2) 0.16146(17) 0.0226(4) Uani 1 1 d . .
H6 H 1.1712 0.7676 0.1615 0.027 Uiso 1 1 calc R U
C7 C 1.0790(3) 0.9193(2) 0.08727(18) 0.0235(4) Uani 1 1 d . .
H7A H 1.1477 0.9903 0.0997 0.028 Uiso 1 1 calc R U
H7B H 1.1035 0.8763 0.0304 0.028 Uiso 1 1 calc R U
C8 C 0.6680(3) 0.6153(2) 0.20040(15) 0.0236(5) Uani 1 1 d . .
H81 H 0.6379 0.6745 0.2493 0.028 Uiso 1 1 calc R U
H82 H 0.7458 0.5597 0.2218 0.028 Uiso 1 1 calc R U
C9 C 0.5503(3) 0.5271(2) 0.17144(15) 0.0203(4) Uani 1 1 d . .
C10 C 0.4130(3) 0.5679(2) 0.18180(17) 0.0248(5) Uani 1 1 d . .
H10 H 0.3934 0.6524 0.2079 0.030 Uiso 1 1 calc R U
C11 C 0.3048(3) 0.4862(2) 0.15422(19) 0.0286(5) Uani 1 1 d . .
H11 H 0.2121 0.5148 0.1619 0.034 Uiso 1 1 calc R U
C12 C 0.3324(3) 0.3628(2) 0.11538(17) 0.0285(5) Uani 1 1 d . .
H12 H 0.2589 0.3070 0.0962 0.034 Uiso 1 1 calc R U
C13 C 0.4686(3) 0.3219(2) 0.10496(18) 0.0306(6) Uani 1 1 d . .
H13 H 0.4878 0.2381 0.0779 0.037 Uiso 1 1 calc R U
C14 C 0.5772(3) 0.4023(2) 0.13375(18) 0.0256(5) Uani 1 1 d . .
H14 H 0.6697 0.3721 0.1277 0.031 Uiso 1 1 calc R U
N1 N 0.9415(2) 0.97754(17) 0.08149(13) 0.0189(4) Uani 1 1 d . .
N2 N 0.9924(2) 0.64676(19) 0.06065(15) 0.0261(4) Uani 1 1 d . .
N3 N 0.9236(2) 0.54636(19) 0.04299(15) 0.0261(4) Uani 1 1 d . .
N4 N 0.8718(3) 0.4522(2) 0.0169(2) 0.0397(6) Uani 1 1 d . .
O1 O 0.9928(2) 1.18644(16) 0.13734(12) 0.0278(4) Uani 1 1 d . .
O2 O 0.7726(2) 1.11432(15) 0.12339(13) 0.0268(4) Uani 1 1 d . .
O3 O 1.0628(2) 0.88378(15) 0.24352(12) 0.0264(4) Uani 1 1 d . .
H3A H 1.0554 0.8225 0.2828 0.040 Uiso 1 1 d R U
O4 O 0.71125(18) 0.69488(14) 0.12515(10) 0.0179(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 0.0033 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
O1 C1 N1 127.4(2)
O1 C1 O2 122.1(2)
N1 C1 O2 110.5(2)
O2 C2 C3 104.89(18)
N1 C3 C4 110.07(16)
N1 C3 C2 100.96(16)
C4 C3 C2 114.13(18)
O4 C4 C3 105.73(16)
O4 C4 C5 112.58(15)
C3 C4 C5 110.90(17)
N2 C5 C4 111.05(18)
N2 C5 C6 105.56(19)
C4 C5 C6 110.62(16)
O3 C6 C7 108.14(17)
O3 C6 C5 110.26(19)
C7 C6 C5 110.08(19)
N1 C7 C6 108.87(19)
O4 C8 C9 108.15(18)
C14 C9 C10 118.9(2)
C14 C9 C8 120.0(2)
C10 C9 C8 121.1(2)
C11 C10 C9 120.7(2)
C12 C11 C10 120.1(2)
C13 C12 C11 119.4(2)
C12 C13 C14 120.8(2)
C13 C14 C9 120.1(3)
C1 N1 C7 122.2(2)
C1 N1 C3 111.78(19)
C7 N1 C3 121.13(16)
N3 N2 C5 116.4(2)
N4 N3 N2 170.6(3)
C1 O2 C2 109.24(17)
C4 O4 C8 112.66(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.224(3)
C1 N1 1.346(3)
C1 O2 1.359(3)
C2 O2 1.457(3)
C2 C3 1.537(3)
C3 N1 1.464(3)
C3 C4 1.534(3)
C4 O4 1.426(2)
C4 C5 1.536(3)
C5 N2 1.498(3)
C5 C6 1.547(3)
C6 O3 1.426(3)
C6 C7 1.528(3)
C7 N1 1.456(3)
C8 O4 1.449(3)
C8 C9 1.506(3)
C9 C14 1.395(3)
C9 C10 1.400(3)
C10 C11 1.391(4)
C11 C12 1.391(4)
C12 C13 1.389(4)
C13 C14 1.393(4)
N2 N3 1.233(3)
N3 N4 1.137(3)
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
O2 C2 C3 N1 -15.5(2)
O2 C2 C3 C4 102.5(2)
N1 C3 C4 O4 -171.07(16)
C2 C3 C4 O4 76.3(2)
N1 C3 C4 C5 -48.8(2)
C2 C3 C4 C5 -161.42(18)
O4 C4 C5 N2 57.7(2)
C3 C4 C5 N2 -60.6(2)
O4 C4 C5 C6 174.56(18)
C3 C4 C5 C6 56.3(2)
N2 C5 C6 O3 -179.47(17)
C4 C5 C6 O3 60.3(2)
N2 C5 C6 C7 61.3(2)
C4 C5 C6 C7 -58.9(2)
O3 C6 C7 N1 -67.1(2)
C5 C6 C7 N1 53.4(2)
O4 C8 C9 C14 87.2(3)
O4 C8 C9 C10 -92.9(3)
C14 C9 C10 C11 -0.6(3)
C8 C9 C10 C11 179.5(2)
C9 C10 C11 C12 -0.4(4)
C10 C11 C12 C13 0.4(4)
C11 C12 C13 C14 0.7(4)
C12 C13 C14 C9 -1.7(4)
C10 C9 C14 C13 1.7(4)
C8 C9 C14 C13 -178.5(2)
O1 C1 N1 C7 17.2(4)
O2 C1 N1 C7 -163.5(2)
O1 C1 N1 C3 172.7(2)
O2 C1 N1 C3 -8.0(3)
C6 C7 N1 C1 101.3(2)
C6 C7 N1 C3 -51.9(3)
C4 C3 N1 C1 -106.2(2)
C2 C3 N1 C1 14.7(2)
C4 C3 N1 C7 49.5(3)
C2 C3 N1 C7 170.5(2)
C4 C5 N2 N3 -71.3(3)
C6 C5 N2 N3 168.8(2)
O1 C1 O2 C2 176.2(2)
N1 C1 O2 C2 -3.2(3)
C3 C2 O2 C1 12.2(3)
C3 C4 O4 C8 -159.37(17)
C5 C4 O4 C8 79.4(2)
C9 C8 O4 C4 179.24(18)
