#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/94/2229401.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229401
loop_
_publ_author_name
'Fadlalla, Mohamed I.'
'Friedrich, Holger B.'
'Maguire, Glenn E. M.'
'Omondi, Bernard'
_publ_section_title
;
 tert-Butyl 2-hydroxy-3-(4-methylbenzenesulfonamido)butanoate
;
_journal_coeditor_code           HG2795
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o648
_journal_paper_doi               10.1107/S1600536811004934
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H23 N O5 S'
_chemical_formula_moiety         'C15 H23 N O5 S'
_chemical_formula_sum            'C15 H23 N O5 S'
_chemical_formula_weight         329.4
_chemical_name_systematic
;
tert-Butyl 2-hydroxy-3-(4-methylbenzenesulfonamido)butanoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                119.342(2)
_cell_angle_beta                 92.307(2)
_cell_angle_gamma                93.422(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6038(8)
_cell_length_b                   9.9059(8)
_cell_length_c                   10.1064(11)
_cell_measurement_reflns_used    24635
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.13
_cell_volume                     833.95(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2007)'
_computing_molecular_graphics
'DIAMOND (Brandenburg & Putz, 2005) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEXII 4K Kappa CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24635
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.3237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                3712
_reflns_number_total             4192
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2795.cif
_cod_data_source_block           I
_cod_database_code               2229401
_cod_database_fobs_code          2229401
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.74584(13) 1.08296(13) 0.93414(13) 0.0208(2) Uani d . 1 . .
H H1A 0.6562 1.118 0.9193 0.031 Uiso calc R 1 . .
H H1B 0.8195 1.1223 0.8942 0.031 Uiso calc R 1 . .
H H1C 0.7685 1.1225 1.0431 0.031 Uiso calc R 1 . .
C C2 0.87462(12) 0.84588(14) 0.86348(14) 0.0241(2) Uani d . 1 . .
H H2A 0.9444 0.8772 0.8132 0.036 Uiso calc R 1 . .
H H2B 0.8629 0.7322 0.8145 0.036 Uiso calc R 1 . .
H H2C 0.9061 0.8896 0.9712 0.036 Uiso calc R 1 . .
C C3 0.61532(13) 0.83957(14) 0.90149(13) 0.0222(2) Uani d . 1 . .
H H3A 0.6156 0.7262 0.8517 0.033 Uiso calc R 1 . .
H H3B 0.5263 0.8661 0.8736 0.033 Uiso calc R 1 . .
H H3C 0.627 0.8836 1.0122 0.033 Uiso calc R 1 . .
C C4 0.73538(11) 0.90605(13) 0.85019(12) 0.0165(2) Uani d . 1 . .
C C5 0.68030(10) 0.71782(12) 0.58068(12) 0.0145(2) Uani d . 1 . .
C C6 0.63194(11) 0.69956(12) 0.42678(12) 0.0151(2) Uani d . 1 . .
H H6 0.7064 0.7491 0.3939 0.018 Uiso calc R 1 . .
C C7 0.49600(11) 0.77696(12) 0.43670(12) 0.0152(2) Uani d . 1 . .
H H7 0.5149 0.891 0.5094 0.018 Uiso calc R 1 . .
C C8 0.44465(12) 0.75423(15) 0.28179(13) 0.0223(2) Uani d . 1 . .
H H8A 0.3603 0.8085 0.2919 0.033 Uiso calc R 1 . .
H H8B 0.4228 0.643 0.2101 0.033 Uiso calc R 1 . .
H H8C 0.5178 0.7965 0.2438 0.033 Uiso calc R 1 . .
C C9 0.12195(11) 0.73713(13) 0.43575(12) 0.0166(2) Uani d . 1 . .
C C10 0.05152(11) 0.58888(13) 0.37062(13) 0.0177(2) Uani d . 1 . .
H H10 0.0739 0.5198 0.4067 0.021 Uiso calc R 1 . .
C C11 -0.05154(11) 0.54303(14) 0.25272(13) 0.0197(2) Uani d . 1 . .
H H11 -0.0984 0.4414 0.2071 0.024 Uiso calc R 1 . .
C C12 -0.08741(11) 0.64442(15) 0.19995(13) 0.0209(2) Uani d . 1 . .
C C13 -0.01768(12) 0.79315(15) 0.26927(14) 0.0233(2) Uani d . 1 . .
H H13 -0.0425 0.8639 0.2362 0.028 Uiso calc R 1 . .
C C14 0.08753(12) 0.84021(14) 0.38584(14) 0.0215(2) Uani d . 1 . .
H H14 0.1352 0.9413 0.4308 0.026 Uiso calc R 1 . .
C C15 -0.19933(13) 0.59239(18) 0.07100(15) 0.0296(3) Uani d . 1 . .
H H15A -0.1592 0.5302 -0.0263 0.044 Uiso calc R 1 . .
H H15B -0.2358 0.6838 0.0733 0.044 Uiso calc R 1 . .
H H15C -0.2756 0.5295 0.0824 0.044 Uiso calc R 1 . .
N N1 0.39695(9) 0.71013(11) 0.50168(10) 0.01484(18) Uani d . 1 . .
O O1 0.70108(8) 0.86607(8) 0.68847(8) 0.01528(15) Uani d . 1 . .
O O2 0.69788(8) 0.60683(9) 0.59739(9) 0.01913(17) Uani d . 1 . .
O O3 0.60741(8) 0.53975(9) 0.31707(9) 0.01922(17) Uani d . 1 . .
H H3 0.6564 0.4879 0.3431 0.029 Uiso calc R 1 . .
O O4 0.21687(9) 0.71817(10) 0.66814(9) 0.02355(18) Uani d . 1 . .
O O5 0.29082(9) 0.95624(10) 0.65376(10) 0.02641(19) Uani d . 1 . .
S S1 0.25877(3) 0.79036(3) 0.58022(3) 0.01691(8) Uani d . 1 . .
H H1D 0.3859(16) 0.6124(18) 0.4581(17) 0.025(4) Uiso d . 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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C2 H2A . . 109.5 ?
C4 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O1 C4 C1 . . 102.44(8) ?
O1 C4 C2 . . 109.60(9) ?
C1 C4 C2 . . 111.41(9) ?
O1 C4 C3 . . 108.99(9) ?
C1 C4 C3 . . 111.22(9) ?
C2 C4 C3 . . 112.66(10) ?
O2 C5 O1 . . 125.85(10) ?
O2 C5 C6 . . 122.05(9) ?
O1 C5 C6 . . 112.09(9) ?
O3 C6 C5 . . 109.87(8) ?
O3 C6 C7 . . 108.58(8) ?
C5 C6 C7 . . 110.83(8) ?
O3 C6 H6 . . 109.2 ?
C5 C6 H6 . . 109.2 ?
C7 C6 H6 . . 109.2 ?
N1 C7 C8 . . 114.28(9) ?
N1 C7 C6 . . 105.79(8) ?
C8 C7 C6 . . 110.98(9) ?
N1 C7 H7 . . 108.5 ?
C8 C7 H7 . . 108.5 ?
C6 C7 H7 . . 108.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 120.57(10) ?
C14 C9 S1 . . 120.59(9) ?
C10 C9 S1 . . 118.82(8) ?
C11 C10 C9 . . 119.49(10) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C12 . . 120.95(11) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C13 C12 C11 . . 118.43(10) ?
C13 C12 C15 . . 121.30(11) ?
C11 C12 C15 . . 120.27(11) ?
C14 C13 C12 . . 121.41(10) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C9 . . 119.13(11) ?
C13 C14 H14 . . 120.4 ?
C9 C14 H14 . . 120.4 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 N1 S1 . . 123.52(7) ?
C7 N1 H1D . . 116.2(10) ?
S1 N1 H1D . . 112.5(10) ?
C5 O1 C4 . . 119.50(8) ?
C6 O3 H3 . . 109.5 ?
O5 S1 O4 . . 120.06(5) ?
O5 S1 N1 . . 107.61(5) ?
O4 S1 N1 . . 105.57(5) ?
O5 S1 C9 . . 108.09(5) ?
O4 S1 C9 . . 106.33(5) ?
N1 S1 C9 . . 108.80(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C4 . 1.5218(15) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C4 . 1.5235(15) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 C4 . 1.5245(16) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 O1 . 1.4978(12) ?
C5 O2 . 1.2115(13) ?
C5 O1 . 1.3277(12) ?
C5 C6 . 1.5244(14) ?
C6 O3 . 1.4161(12) ?
C6 C7 . 1.5353(14) ?
C6 H6 . 1 ?
C7 N1 . 1.4750(13) ?
C7 C8 . 1.5245(15) ?
C7 H7 . 1 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C14 . 1.3921(15) ?
C9 C10 . 1.3949(15) ?
C9 S1 . 1.7733(11) ?
C10 C11 . 1.3881(15) ?
C10 H10 . 0.95 ?
C11 C12 . 1.4012(16) ?
C11 H11 . 0.95 ?
C12 C13 . 1.3938(18) ?
C12 C15 . 1.5106(16) ?
C13 C14 . 1.3914(17) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
N1 S1 . 1.6172(9) ?
N1 H1D . 0.842(16) ?
O3 H3 . 0.84 ?
O4 S1 . 1.4422(9) ?
O5 S1 . 1.4393(9) ?
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
N1 H1D O2 2_666 0.842(16) 2.059(16) 2.8625(12) 159.5(14)
O3 H3 O4 2_666 0.84 2.40 3.2041(12) 162
C1 H1C O4 2_677 0.98 2.54 3.4936(14) 164
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C5 C6 O3 . . . . 2.43(14) ?
O1 C5 C6 O3 . . . . -178.31(8) ?
O2 C5 C6 C7 . . . . 122.43(11) ?
O1 C5 C6 C7 . . . . -58.31(11) ?
O3 C6 C7 N1 . . . . 67.16(10) ?
C5 C6 C7 N1 . . . . -53.61(11) ?
O3 C6 C7 C8 . . . . -57.32(11) ?
C5 C6 C7 C8 . . . . -178.09(9) ?
C14 C9 C10 C11 . . . . 1.46(16) ?
S1 C9 C10 C11 . . . . -177.12(8) ?
C9 C10 C11 C12 . . . . -1.07(17) ?
C10 C11 C12 C13 . . . . -0.37(17) ?
C10 C11 C12 C15 . . . . 179.70(10) ?
C11 C12 C13 C14 . . . . 1.47(17) ?
C15 C12 C13 C14 . . . . -178.60(11) ?
C12 C13 C14 C9 . . . . -1.10(18) ?
C10 C9 C14 C13 . . . . -0.39(17) ?
S1 C9 C14 C13 . . . . 178.17(9) ?
C8 C7 N1 S1 . . . . -76.81(11) ?
C6 C7 N1 S1 . . . . 160.79(7) ?
O2 C5 O1 C4 . . . . -6.69(15) ?
C6 C5 O1 C4 . . . . 174.08(8) ?
C1 C4 O1 C5 . . . . -178.29(9) ?
C2 C4 O1 C5 . . . . 63.33(12) ?
C3 C4 O1 C5 . . . . -60.39(12) ?
C7 N1 S1 O5 . . . . -33.34(10) ?
C7 N1 S1 O4 . . . . -162.69(8) ?
C7 N1 S1 C9 . . . . 83.54(9) ?
C14 C9 S1 O5 . . . . 15.26(11) ?
C10 C9 S1 O5 . . . . -166.16(9) ?
C14 C9 S1 O4 . . . . 145.40(9) ?
C10 C9 S1 O4 . . . . -36.01(10) ?
C14 C9 S1 N1 . . . . -101.32(10) ?
C10 C9 S1 N1 . . . . 77.26(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2036090
