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#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024358.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_4024358
loop_
_publ_author_name
'Jacob S. Kanady'
'John D. Nguyen'
'Joseph W. Ziller'
'Christopher D. Vanderwal'
_publ_section_title
;
Synthesis and Characterization of All Four Diastereomers of
3,4-Dichloro-2-pentanol, Motifs Relevant to the Chlorosulfolipids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2175
_journal_page_last               2178
_journal_paper_doi               10.1021/jo802390e
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C12 H16 Cl2 O3 S'
_chemical_formula_weight         311.21
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.5800(10)
_cell_angle_beta                 100.5940(10)
_cell_angle_gamma                104.7760(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5215(4)
_cell_length_b                   10.2918(5)
_cell_length_c                   10.5956(9)
_cell_measurement_temperature    103(2)
_cell_volume                     701.45(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8373
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.8481
_exptl_absorpt_correction_T_min  0.8386
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0243
_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)+(0.0419P)²+0.2526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                3213
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802390e_si_003.cif
_cod_data_source_block           cdv6
_cod_database_code               4024358
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27321(4) 0.16481(3) 0.74743(3) 0.01466(8) Uani 1 1 d . . .
Cl1 Cl -0.00182(5) 0.40285(3) 1.13145(3) 0.02512(9) Uani 1 1 d . . .
Cl2 Cl -0.25102(4) -0.05826(3) 0.81627(3) 0.01875(8) Uani 1 1 d . . .
O1 O 0.04956(11) 0.10224(8) 0.72674(8) 0.01530(16) Uani 1 1 d . . .
O2 O 0.37950(12) 0.23473(9) 0.89664(9) 0.01965(17) Uani 1 1 d . . .
O3 O 0.30615(13) 0.03980(9) 0.65179(10) 0.02193(18) Uani 1 1 d . . .
C1 C -0.21731(18) 0.14543(14) 1.12721(13) 0.0212(2) Uani 1 1 d . . .
C2 C -0.17466(16) 0.21389(12) 1.02631(12) 0.0169(2) Uani 1 1 d . . .
C3 C -0.08384(15) 0.13126(11) 0.91994(11) 0.0138(2) Uani 1 1 d . . .
C4 C -0.03504(15) 0.19857(12) 0.81846(12) 0.0147(2) Uani 1 1 d . . .
C5 C -0.20345(18) 0.20536(14) 0.72144(14) 0.0207(2) Uani 1 1 d . . .
C6 C 0.29450(15) 0.30331(12) 0.68579(11) 0.0144(2) Uani 1 1 d . . .
C7 C 0.41464(16) 0.44967(12) 0.77514(12) 0.0159(2) Uani 1 1 d . . .
C8 C 0.42698(16) 0.55755(12) 0.72429(12) 0.0166(2) Uani 1 1 d . . .
C9 C 0.31913(15) 0.52081(12) 0.58582(12) 0.0151(2) Uani 1 1 d . . .
C10 C 0.20095(17) 0.37202(13) 0.49800(12) 0.0196(2) Uani 1 1 d . . .
C11 C 0.18752(17) 0.26237(13) 0.54585(12) 0.0196(2) Uani 1 1 d . . .
C12 C 0.32614(18) 0.63623(14) 0.52963(13) 0.0189(2) Uani 1 1 d . . .
H1A H -0.315(2) 0.048(2) 1.0746(18) 0.028(4) Uiso 1 1 d . . .
H1B H -0.101(2) 0.1346(18) 1.1749(17) 0.027(4) Uiso 1 1 d . . .
H1C H -0.260(3) 0.206(2) 1.1956(19) 0.032(4) Uiso 1 1 d . . .
H2A H -0.285(2) 0.2222(17) 0.9796(16) 0.019(4) Uiso 1 1 d . . .
H3A H 0.033(2) 0.1257(16) 0.9693(15) 0.015(3) Uiso 1 1 d . . .
H4A H 0.062(2) 0.2960(17) 0.8746(15) 0.015(3) Uiso 1 1 d . . .
H5A H -0.302(3) 0.112(2) 0.6708(19) 0.032(4) Uiso 1 1 d . . .
H5B H -0.158(3) 0.246(2) 0.658(2) 0.037(5) Uiso 1 1 d . . .
H5C H -0.256(2) 0.2688(18) 0.7758(17) 0.023(4) Uiso 1 1 d . . .
H7A H 0.487(2) 0.4739(18) 0.8672(18) 0.025(4) Uiso 1 1 d . . .
H8A H 0.507(2) 0.6577(18) 0.7869(17) 0.020(4) Uiso 1 1 d . . .
H10A H 0.132(2) 0.3468(19) 0.4050(19) 0.031(4) Uiso 1 1 d . . .
H11A H 0.107(2) 0.1621(18) 0.4858(17) 0.022(4) Uiso 1 1 d . . .
H12A H 0.357(3) 0.608(2) 0.441(2) 0.052(6) Uiso 1 1 d . . .
H12B H 0.410(3) 0.728(3) 0.591(2) 0.055(6) Uiso 1 1 d . . .
H12C H 0.206(4) 0.650(3) 0.514(3) 0.069(7) Uiso 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
O3 S1 O2 119.83(5) . . ?
O3 S1 O1 103.43(5) . . ?
O2 S1 O1 109.59(5) . . ?
O3 S1 C6 110.72(5) . . ?
O2 S1 C6 108.61(5) . . ?
O1 S1 C6 103.34(5) . . ?
C4 O1 S1 118.85(7) . . ?
C1 C2 C3 113.63(10) . . ?
C1 C2 Cl1 108.37(8) . . ?
C3 C2 Cl1 106.63(8) . . ?
C4 C3 C2 115.21(9) . . ?
C4 C3 Cl2 108.89(7) . . ?
C2 C3 Cl2 107.52(7) . . ?
O1 C4 C5 107.33(9) . . ?
O1 C4 C3 105.95(8) . . ?
C5 C4 C3 116.06(9) . . ?
C7 C6 C11 121.22(10) . . ?
C7 C6 S1 120.28(8) . . ?
C11 C6 S1 118.49(8) . . ?
C6 C7 C8 119.14(10) . . ?
C7 C8 C9 121.05(10) . . ?
C8 C9 C10 118.39(10) . . ?
C8 C9 C12 122.04(10) . . ?
C10 C9 C12 119.57(10) . . ?
C11 C10 C9 121.60(11) . . ?
C10 C11 C6 118.58(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
S1 O3 1.4281(9) . ?
S1 O2 1.4358(9) . ?
S1 O1 1.5813(8) . ?
S1 C6 1.7581(11) . ?
Cl1 C2 1.8159(12) . ?
Cl2 C3 1.8047(11) . ?
O1 C4 1.4740(13) . ?
C1 C2 1.5189(16) . ?
C2 C3 1.5279(16) . ?
C3 C4 1.5278(15) . ?
C4 C5 1.5117(15) . ?
C6 C7 1.3871(15) . ?
C6 C11 1.3973(15) . ?
C7 C8 1.3920(16) . ?
C8 C9 1.3969(15) . ?
C9 C10 1.3980(16) . ?
C9 C12 1.5060(15) . ?
C10 C11 1.3865(17) . ?
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
O3 S1 O1 C4 175.18(7) . . . . ?
O2 S1 O1 C4 46.30(8) . . . . ?
C6 S1 O1 C4 -69.33(8) . . . . ?
C1 C2 C3 C4 -178.84(9) . . . . ?
Cl1 C2 C3 C4 -59.51(11) . . . . ?
C1 C2 C3 Cl2 59.57(11) . . . . ?
Cl1 C2 C3 Cl2 178.89(5) . . . . ?
S1 O1 C4 C5 126.28(8) . . . . ?
S1 O1 C4 C3 -109.12(8) . . . . ?
C2 C3 C4 O1 -179.96(9) . . . . ?
Cl2 C3 C4 O1 -59.11(9) . . . . ?
C2 C3 C4 C5 -60.96(13) . . . . ?
Cl2 C3 C4 C5 59.89(11) . . . . ?
O3 S1 C6 C7 -127.96(9) . . . . ?
O2 S1 C6 C7 5.54(11) . . . . ?
O1 S1 C6 C7 121.87(9) . . . . ?
O3 S1 C6 C11 52.28(10) . . . . ?
O2 S1 C6 C11 -174.22(9) . . . . ?
O1 S1 C6 C11 -57.90(10) . . . . ?
C11 C6 C7 C8 0.58(16) . . . . ?
S1 C6 C7 C8 -179.18(8) . . . . ?
C6 C7 C8 C9 0.65(17) . . . . ?
C7 C8 C9 C10 -1.29(17) . . . . ?
C7 C8 C9 C12 178.41(10) . . . . ?
C8 C9 C10 C11 0.75(17) . . . . ?
C12 C9 C10 C11 -178.96(11) . . . . ?
C9 C10 C11 C6 0.43(18) . . . . ?
C7 C6 C11 C10 -1.11(17) . . . . ?
S1 C6 C11 C10 178.65(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091061
