#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:30:12 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151625.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_7151625
loop_
_publ_author_name
'Cren, Sylvaine'
'Gurcha, Sudagar S.'
'Blake, Alexander J.'
'Besra, Gurdyal S.'
'Thomas, Neil R.'
_publ_section_title
;
 Synthesis and biological evaluation of new inhibitors of UDP-Galf
 transferase--a key enzyme in M. tuberculosis cell wall biosynthesis.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2418
_journal_page_last               2420
_journal_paper_doi               10.1039/b411554f
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C14 H25 N O5'
_chemical_formula_sum            'C14 H25 N O5'
_chemical_formula_weight         287.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens
'OH from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.266(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.668(2)
_cell_length_b                   5.7076(8)
_cell_length_c                   18.373(3)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.2
_cell_volume                     1531.7(4)
_computing_cell_refinement       'Bruker SAINT version 6.02a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9434
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    'rigid rotating group; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_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)+(0.058P)²+0.37P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                2821
_reflns_number_total             3464
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b411554f.txt
_cod_data_source_block           IPOSNO
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.68189(7) 0.25006(19) 0.64351(6) 0.0246(2) Uani 1 1 d . . .
C2 C 0.72899(9) 0.4482(2) 0.68068(7) 0.0254(3) Uani 1 1 d . . .
H2A H 0.7510 0.4079 0.7317 0.030 Uiso 1 1 calc R . .
H2B H 0.6885 0.5869 0.6808 0.030 Uiso 1 1 calc R . .
C3 C 0.80882(9) 0.4916(2) 0.63474(7) 0.0273(3) Uani 1 1 d . . .
H3 H 0.8611 0.3873 0.6521 0.033 Uiso 1 1 calc R . .
C4 C 0.77134(8) 0.4182(2) 0.55861(7) 0.0249(3) Uani 1 1 d . . .
H4 H 0.7270 0.5404 0.5387 0.030 Uiso 1 1 calc R . .
C5 C 0.71782(9) 0.1969(2) 0.57312(7) 0.0242(3) Uani 1 1 d . . .
H5A H 0.6676 0.1702 0.5342 0.029 Uiso 1 1 calc R . .
H5B H 0.7582 0.0577 0.5770 0.029 Uiso 1 1 calc R . .
O6 O 0.83871(6) 0.72743(16) 0.63626(5) 0.0288(2) Uani 1 1 d . . .
H6O H 0.8689 0.7551 0.6764 0.043 Uiso 1 1 calc R . .
C7 C 0.84180(9) 0.3857(3) 0.50564(7) 0.0303(3) Uani 1 1 d . . .
H7 H 0.8906 0.2769 0.5270 0.036 Uiso 1 1 calc R . .
C8 C 0.88562(9) 0.6069(3) 0.47928(7) 0.0310(3) Uani 1 1 d . . .
H8A H 0.8405 0.7356 0.4717 0.037 Uiso 1 1 calc R . .
H8B H 0.9372 0.6589 0.5140 0.037 Uiso 1 1 calc R . .
O9 O 0.91677(6) 0.53169(18) 0.41167(5) 0.0333(2) Uani 1 1 d . . .
O10 O 0.80015(7) 0.28994(18) 0.43896(5) 0.0327(2) Uani 1 1 d . . .
C10 C 0.85244(9) 0.3632(3) 0.38088(7) 0.0291(3) Uani 1 1 d . . .
C11 C 0.90466(11) 0.1602(3) 0.35333(9) 0.0409(4) Uani 1 1 d . . .
H11A H 0.9456 0.0954 0.3935 0.061 Uiso 1 1 calc R . .
H11B H 0.9409 0.2137 0.3143 0.061 Uiso 1 1 calc R . .
H11C H 0.8616 0.0389 0.3343 0.061 Uiso 1 1 calc R . .
C12 C 0.78721(10) 0.4754(3) 0.32261(9) 0.0421(4) Uani 1 1 d . . .
H12A H 0.7555 0.6062 0.3439 0.063 Uiso 1 1 calc R . .
H12B H 0.7422 0.3591 0.3031 0.063 Uiso 1 1 calc R . .
H12C H 0.8216 0.5336 0.2831 0.063 Uiso 1 1 calc R . .
C13 C 0.60755(8) 0.1544(2) 0.66869(7) 0.0215(3) Uani 1 1 d . . .
O13 O 0.57524(6) 0.21922(16) 0.72430(5) 0.0257(2) Uani 1 1 d . . .
O14 O 0.57400(6) -0.02020(16) 0.62501(5) 0.0245(2) Uani 1 1 d . . .
C14 C 0.48463(8) -0.1279(2) 0.63607(7) 0.0239(3) Uani 1 1 d . . .
C15 C 0.48510(9) -0.2373(2) 0.71144(8) 0.0287(3) Uani 1 1 d . . .
H15A H 0.5347 -0.3525 0.7182 0.043 Uiso 1 1 calc R . .
H15B H 0.4263 -0.3151 0.7160 0.043 Uiso 1 1 calc R . .
H15C H 0.4946 -0.1149 0.7488 0.043 Uiso 1 1 calc R . .
C16 C 0.40950(9) 0.0539(2) 0.62180(8) 0.0298(3) Uani 1 1 d . . .
H16A H 0.4153 0.1725 0.6605 0.045 Uiso 1 1 calc R . .
H16B H 0.3496 -0.0225 0.6212 0.045 Uiso 1 1 calc R . .
H16C H 0.4151 0.1290 0.5745 0.045 Uiso 1 1 calc R . .
C17 C 0.47776(10) -0.3160(2) 0.57755(8) 0.0314(3) Uani 1 1 d . . .
H17A H 0.5269 -0.4307 0.5881 0.047 Uiso 1 1 calc R . .
H17B H 0.4836 -0.2441 0.5298 0.047 Uiso 1 1 calc R . .
H17C H 0.4183 -0.3948 0.5770 0.047 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C2 121.27(10) . . ?
C13 N1 C5 126.01(11) . . ?
C2 N1 C5 112.20(10) . . ?
N1 C2 C3 102.78(10) . . ?
O6 C3 C4 111.52(11) . . ?
O6 C3 C2 113.33(11) . . ?
C4 C3 C2 103.53(10) . . ?
C7 C4 C3 114.94(11) . . ?
C7 C4 C5 114.17(11) . . ?
C3 C4 C5 102.53(10) . . ?
N1 C5 C4 102.40(10) . . ?
O10 C7 C4 109.84(11) . . ?
O10 C7 C8 101.86(11) . . ?
C4 C7 C8 116.33(12) . . ?
O9 C8 C7 101.90(11) . . ?
C10 O9 C8 107.14(10) . . ?
C7 O10 C10 108.14(10) . . ?
O9 C10 O10 106.32(10) . . ?
O9 C10 C11 108.32(11) . . ?
O10 C10 C11 110.49(12) . . ?
O9 C10 C12 110.37(12) . . ?
O10 C10 C12 107.69(11) . . ?
C11 C10 C12 113.42(13) . . ?
O13 C13 N1 123.75(12) . . ?
O13 C13 O14 125.08(11) . . ?
N1 C13 O14 111.17(10) . . ?
C13 O14 C14 120.45(9) . . ?
O14 C14 C17 101.48(10) . . ?
O14 C14 C15 111.49(10) . . ?
C17 C14 C15 110.49(11) . . ?
O14 C14 C16 109.29(10) . . ?
C17 C14 C16 111.19(11) . . ?
C15 C14 C16 112.38(11) . . ?
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
N1 C2 1.4613(16) . ?
N1 C5 1.4722(16) . ?
N1 C13 1.3393(16) . ?
C2 C3 1.5252(18) . ?
C3 O6 1.4151(16) . ?
C3 C4 1.5143(18) . ?
C4 C7 1.4949(18) . ?
C4 C5 1.5234(18) . ?
C7 O10 1.4267(16) . ?
C7 C8 1.5161(19) . ?
C8 O9 1.4284(16) . ?
O9 C10 1.4271(16) . ?
O10 C10 1.4326(15) . ?
C10 C11 1.502(2) . ?
C10 C12 1.511(2) . ?
C13 O13 1.2225(15) . ?
C13 O14 1.3440(15) . ?
O14 C14 1.4788(14) . ?
C14 C15 1.5186(18) . ?
C14 C16 1.5189(18) . ?
C14 C17 1.5161(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6O O13 0.84 1.94 2.7506(13) 162 2_656
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
C13 N1 C2 C3 178.55(11) . . . . ?
C5 N1 C2 C3 -9.27(14) . . . . ?
N1 C2 C3 O6 151.89(10) . . . . ?
N1 C2 C3 C4 30.91(13) . . . . ?
O6 C3 C4 C7 72.37(15) . . . . ?
C2 C3 C4 C7 -165.44(12) . . . . ?
O6 C3 C4 C5 -163.17(10) . . . . ?
C2 C3 C4 C5 -40.98(13) . . . . ?
C13 N1 C5 C4 155.90(12) . . . . ?
C2 N1 C5 C4 -15.83(13) . . . . ?
C7 C4 C5 N1 159.43(11) . . . . ?
C3 C4 C5 N1 34.46(12) . . . . ?
C3 C4 C7 O10 173.00(11) . . . . ?
C5 C4 C7 O10 54.90(15) . . . . ?
C3 C4 C7 C8 -72.01(16) . . . . ?
C5 C4 C7 C8 169.89(11) . . . . ?
O10 C7 C8 O9 -37.63(13) . . . . ?
C4 C7 C8 O9 -157.03(11) . . . . ?
C7 C8 O9 C10 33.54(14) . . . . ?
C4 C7 O10 C10 152.46(12) . . . . ?
C8 C7 O10 C10 28.57(14) . . . . ?
C8 O9 C10 O10 -16.63(15) . . . . ?
C8 O9 C10 C11 -135.40(12) . . . . ?
C8 O9 C10 C12 99.89(13) . . . . ?
C7 O10 C10 O9 -8.69(15) . . . . ?
C7 O10 C10 C11 108.64(13) . . . . ?
C7 O10 C10 C12 -126.99(13) . . . . ?
C2 N1 C13 O13 -1.87(19) . . . . ?
C5 N1 C13 O13 -172.91(12) . . . . ?
C2 N1 C13 O14 178.18(10) . . . . ?
C5 N1 C13 O14 7.14(17) . . . . ?
O13 C13 O14 C14 9.01(18) . . . . ?
N1 C13 O14 C14 -171.04(10) . . . . ?
C13 O14 C14 C17 -178.04(10) . . . . ?
C13 O14 C14 C15 -60.41(14) . . . . ?
C13 O14 C14 C16 64.45(14) . . . . ?
