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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031994.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_4031994
loop_
_publ_author_name
'Liang, Xiaofei'
'Gopalaswamy, Ramesh'
'Navas, 3rd, Frank'
'Toone, Eric J.'
'Zhou, Pei'
_publ_section_title
;
 A Scalable Synthesis of the Difluoromethyl-allo-threonyl
 Hydroxamate-Based LpxC Inhibitor LPC-058.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4393
_journal_page_last               4398
_journal_paper_doi               10.1021/acs.joc.6b00589
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H27 F2 N O7 S'
_chemical_formula_weight         415.45
_chemical_name_common            XFL-13-32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3347(2)
_cell_length_b                   12.7819(4)
_cell_length_c                   22.8824(7)
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.7403
_cell_measurement_theta_min      2.3893
_cell_volume                     1852.78(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27049
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.78
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0303
_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)+(0.0372P)²+0.2708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                3755
_reflns_number_total             4195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00589_si_002.cif
_cod_data_source_block           I
_cod_database_code               4031994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.57368(7) 0.28632(3) 0.593476(18) 0.01258(9) Uani d . 1
F F1 -0.34399(17) 0.61596(9) 0.50106(5) 0.0254(3) Uani d . 1
F F2 -0.18999(18) 0.74054(8) 0.54991(5) 0.0229(3) Uani d . 1
O O2 0.3185(2) 0.46397(11) 0.46531(5) 0.0177(3) Uani d . 1
O O1 0.0331(2) 0.52411(11) 0.41729(5) 0.0217(3) Uani d . 1
O O3 -0.1588(2) 0.54708(10) 0.60399(5) 0.0166(3) Uani d . 1
H H3 -0.2563 0.506 0.5944 0.025 Uiso calc R 1
O O4 0.5022(2) 0.23812(10) 0.53919(5) 0.0178(3) Uani d . 1
O O5 0.79407(19) 0.26702(10) 0.60725(5) 0.0173(3) Uani d . 1
O O6 0.52121(18) 0.39834(9) 0.59501(5) 0.0151(3) Uani d . 1
O O7 0.1456(2) 0.39524(11) 0.68299(5) 0.0190(3) Uani d . 1
N N1 0.1034(2) 0.39000(12) 0.55284(6) 0.0134(3) Uani d . 1
H H1A 0.109 0.3291 0.5323 0.02 Uiso calc R 1
H H1B 0.0303 0.3796 0.5866 0.02 Uiso calc R 1
H H1C 0.2368 0.4115 0.5614 0.02 Uiso calc R 1
C C6 0.1709(3) 0.61763(15) 0.57648(8) 0.0175(4) Uani d . 1
H H6A 0.1432 0.6835 0.597 0.026 Uiso calc R 1
H H6B 0.265 0.6307 0.5433 0.026 Uiso calc R 1
H H6C 0.2381 0.5681 0.6034 0.026 Uiso calc R 1
C C3 -0.0366(3) 0.57184(14) 0.55446(7) 0.0137(4) Uani d . 1
C C2 -0.0039(3) 0.47109(14) 0.51737(7) 0.0129(3) Uani d . 1
H H2 -0.1469 0.4436 0.5069 0.015 Uiso calc R 1
C C1 0.1164(3) 0.48935(14) 0.46034(7) 0.0145(4) Uani d . 1
C C5 0.4438(3) 0.47617(16) 0.41256(8) 0.0223(4) Uani d . 1
H H5A 0.3845 0.4325 0.3814 0.033 Uiso calc R 1
H H5B 0.5895 0.4546 0.4204 0.033 Uiso calc R 1
H H5C 0.4418 0.5496 0.4003 0.033 Uiso calc R 1
C C4 -0.1512(3) 0.65310(15) 0.51709(8) 0.0176(4) Uani d . 1
H H4 -0.0655 0.6712 0.4818 0.021 Uiso calc R 1
C C15 0.5328(3) 0.10401(16) 0.76838(8) 0.0212(4) Uani d . 1
H H15A 0.5015 0.0648 0.8041 0.032 Uiso calc R 1
H H15B 0.6728 0.1361 0.7717 0.032 Uiso calc R 1
H H15C 0.5306 0.0564 0.7348 0.032 Uiso calc R 1
C C14 0.3674(3) 0.18913(14) 0.75983(7) 0.0152(4) Uani d . 1
C C8 0.4204(3) 0.26782(13) 0.70934(7) 0.0126(3) Uani d . 1
C C7 0.4188(3) 0.22209(14) 0.64789(7) 0.0131(3) Uani d . 1
H H7A 0.2707 0.2207 0.6341 0.016 Uiso calc R 1
H H7B 0.4673 0.1486 0.6505 0.016 Uiso calc R 1
C C11 0.3733(3) 0.27457(15) 0.80815(7) 0.0172(4) Uani d . 1
H H11 0.3445 0.2483 0.8485 0.021 Uiso calc R 1
C C12 0.5950(3) 0.32275(16) 0.79960(7) 0.0184(4) Uani d . 1
H H12A 0.7045 0.2803 0.8194 0.022 Uiso calc R 1
H H12B 0.6005 0.3952 0.8148 0.022 Uiso calc R 1
C C13 0.6246(3) 0.32071(14) 0.73215(7) 0.0146(4) Uani d . 1
H H13A 0.639 0.3925 0.7164 0.017 Uiso calc R 1
H H13B 0.751 0.2796 0.7212 0.017 Uiso calc R 1
C C10 0.2149(3) 0.35560(16) 0.78572(7) 0.0192(4) Uani d . 1
H H10A 0.0687 0.3372 0.7971 0.023 Uiso calc R 1
H H10B 0.2484 0.4265 0.8004 0.023 Uiso calc R 1
C C9 0.2456(3) 0.34845(14) 0.71963(7) 0.0134(4) Uani d . 1
C C16 0.1525(3) 0.13542(16) 0.75224(8) 0.0197(4) Uani d . 1
H H16A 0.1599 0.0857 0.7197 0.03 Uiso calc R 1
H H16B 0.0444 0.1883 0.744 0.03 Uiso calc R 1
H H16C 0.1159 0.098 0.7882 0.03 Uiso calc R 1
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O4 S1 O6 111.19(8)
O4 S1 C7 103.25(8)
O5 S1 O4 114.29(8)
O5 S1 O6 112.18(7)
O5 S1 C7 107.39(8)
O6 S1 C7 107.88(8)
C1 O2 C5 115.47(14)
C3 O3 H3 109.5
H1A N1 H1B 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C2 N1 H1A 109.5
C2 N1 H1B 109.5
C2 N1 H1C 109.5
H6A C6 H6B 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C3 C6 H6A 109.5
C3 C6 H6B 109.5
C3 C6 H6C 109.5
O3 C3 C6 107.13(13)
O3 C3 C2 109.02(14)
O3 C3 C4 109.96(14)
C6 C3 C2 112.55(15)
C6 C3 C4 109.49(15)
C4 C3 C2 108.67(13)
N1 C2 C3 109.94(13)
N1 C2 H2 107.5
N1 C2 C1 110.22(14)
C3 C2 H2 107.5
C1 C2 C3 113.91(15)
C1 C2 H2 107.5
O2 C1 C2 111.77(14)
O1 C1 O2 125.74(16)
O1 C1 C2 122.48(16)
O2 C5 H5A 109.5
O2 C5 H5B 109.5
O2 C5 H5C 109.5
H5A C5 H5B 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
F1 C4 F2 105.76(15)
F1 C4 C3 109.88(15)
F1 C4 H4 110.5
F2 C4 C3 109.45(14)
F2 C4 H4 110.5
C3 C4 H4 110.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
C14 C15 H15C 109.5
C15 C14 C8 113.93(15)
C15 C14 C11 113.20(15)
C15 C14 C16 107.79(15)
C11 C14 C8 93.91(13)
C16 C14 C8 113.15(14)
C16 C14 C11 114.59(14)
C7 C8 C14 115.64(14)
C7 C8 C13 118.93(15)
C7 C8 C9 113.32(14)
C13 C8 C14 102.13(13)
C9 C8 C14 99.43(13)
C9 C8 C13 104.96(13)
S1 C7 H7A 107.9
S1 C7 H7B 107.9
C8 C7 S1 117.64(12)
C8 C7 H7A 107.9
C8 C7 H7B 107.9
H7A C7 H7B 107.2
C14 C11 H11 114.6
C12 C11 C14 102.23(13)
C12 C11 H11 114.6
C10 C11 C14 102.77(14)
C10 C11 H11 114.6
C10 C11 C12 106.48(16)
C11 C12 H12A 111.1
C11 C12 H12B 111.1
C11 C12 C13 103.21(14)
H12A C12 H12B 109.1
C13 C12 H12A 111.1
C13 C12 H12B 111.1
C8 C13 C12 103.94(14)
C8 C13 H13A 111.0
C8 C13 H13B 111.0
C12 C13 H13A 111.0
C12 C13 H13B 111.0
H13A C13 H13B 109.0
C11 C10 H10A 111.4
C11 C10 H10B 111.4
H10A C10 H10B 109.2
C9 C10 C11 101.99(14)
C9 C10 H10A 111.4
C9 C10 H10B 111.4
O7 C9 C8 127.24(15)
O7 C9 C10 126.17(16)
C10 C9 C8 106.55(14)
C14 C16 H16A 109.5
C14 C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.4585(12)
S1 O5 1.4523(13)
S1 O6 1.4704(13)
S1 C7 1.7852(17)
F1 C4 1.361(2)
F2 C4 1.369(2)
O2 C1 1.326(2)
O2 C5 1.453(2)
O1 C1 1.202(2)
O3 H3 0.84
O3 C3 1.409(2)
O7 C9 1.209(2)
N1 H1A 0.91
N1 H1B 0.91
N1 H1C 0.91
N1 C2 1.482(2)
C6 H6A 0.98
C6 H6B 0.98
C6 H6C 0.98
C6 C3 1.524(2)
C3 C2 1.556(2)
C3 C4 1.529(3)
C2 H2 1.0
C2 C1 1.529(2)
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
C4 H4 1.0
C15 H15A 0.98
C15 H15B 0.98
C15 H15C 0.98
C15 C14 1.523(3)
C14 C8 1.568(2)
C14 C11 1.555(3)
C14 C16 1.535(3)
C8 C7 1.523(2)
C8 C13 1.550(2)
C8 C9 1.531(2)
C7 H7A 0.99
C7 H7B 0.99
C11 H11 1.0
C11 C12 1.545(2)
C11 C10 1.531(3)
C12 H12A 0.99
C12 H12B 0.99
C12 C13 1.555(2)
C13 H13A 0.99
C13 H13B 0.99
C10 H10A 0.99
C10 H10B 0.99
C10 C9 1.527(2)
C16 H16A 0.98
C16 H16B 0.98
C16 H16C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O6 1_455 0.84 1.97 2.7864(18) 163.9
N1 H1A O4 2_456 0.91 1.97 2.7435(19) 142.1
N1 H1B O5 1_455 0.91 2.13 2.8036(19) 130.1
N1 H1B O7 . 0.91 2.33 2.9909(18) 129.1
N1 H1C O6 . 0.91 1.97 2.8192(19) 155.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094706
