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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235312.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_7235312
loop_
_publ_author_name
'Lu, Yuhua'
'Bolokowicz, Andrew. J.'
'Reeb, Sarah A.'
'Wiseman, Joshua D.'
'Wheeler, Kraig A.'
_publ_section_title
;
 Chiral transmission to crystal photodimerizations of leucine--methionine
 quasiracemic assemblies
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              8125
_journal_paper_doi               10.1039/c3ra47270a
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C15 H19 N O6 S'
_chemical_formula_sum            'C15 H19 N O6 S'
_chemical_formula_weight         341.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                97.853(11)
_cell_angle_beta                 103.477(8)
_cell_angle_gamma                100.941(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0252(15)
_cell_length_b                   8.1514(16)
_cell_length_c                   14.875(3)
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.076
_cell_measurement_theta_min      3.111
_cell_volume                     798.6(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14209
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.971
_diffrn_reflns_theta_min         3.111
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.2373
_refine_ls_R_factor_gt           0.1915
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1688P)²+7.9708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4683
_refine_ls_wR_factor_ref         0.4949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1689
_reflns_number_total             2700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3ra47270a.cif
_cod_data_source_block           kaw114a
_cod_database_code               7235312
_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   0.673
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4725(7) 0.1946(5) 0.7794(4) 0.1062(18) Uani 1 1 d . . . . .
O1 O 1.1071(16) 1.1020(11) 1.2332(7) 0.089(3) Uani 1 1 d D . . . .
H20 H 1.1263 1.1955 1.2666 0.107 Uiso 1 1 calc DR U . . .
O2 O 0.8974(14) 1.2073(12) 1.1323(7) 0.084(3) Uani 1 1 d . . . . .
O3 O 0.9530(15) 0.4706(12) 0.7722(7) 0.090(3) Uani 1 1 d D . . . .
H21 H 1.0242 0.5672 0.7848 0.109 Uiso 1 1 calc DR U . . .
O4 O 0.7517(17) 0.5808(12) 0.6678(7) 0.096(3) Uani 1 1 d . . . . .
O5 O 0.480(2) 0.0689(17) 0.8371(12) 0.154(6) Uani 1 1 d . . . . .
O6 O 0.2874(19) 0.1952(16) 0.7135(11) 0.152(6) Uani 1 1 d . . . . .
N1 N 0.635(2) 0.1747(15) 0.7217(9) 0.095(4) Uani 1 1 d D . . . .
H22 H 0.7006 0.0973 0.7319 0.114 Uiso 1 1 calc DR U . . .
C1 C 0.990(2) 1.0969(15) 1.1564(10) 0.074(4) Uani 1 1 d . . . . .
C2 C 0.896(4) 0.897(4) 1.099(2) 0.063(10) Uani 0.40(3) 1 d . . P A 1
H2 H 0.9526 0.8118 1.1212 0.076 Uiso 0.40(3) 1 calc R U P A 1
C3 C 0.743(7) 0.856(5) 1.023(2) 0.075(12) Uani 0.40(3) 1 d . . P A 1
H3 H 0.6748 0.9379 1.0039 0.091 Uiso 0.40(3) 1 calc R U P A 1
C4 C 0.682(5) 0.687(4) 0.969(2) 0.063(8) Uani 0.40(3) 1 d D U P A 1
C5 C 0.548(5) 0.676(5) 0.881(2) 0.063(10) Uani 0.40(3) 1 d D U P A 1
H5 H 0.5045 0.7715 0.8648 0.076 Uiso 0.40(3) 1 calc R U P A 1
C6 C 0.480(5) 0.523(5) 0.819(2) 0.063(10) Uani 0.40(3) 1 d D U P A 1
H6 H 0.3920 0.5095 0.7596 0.075 Uiso 0.40(3) 1 calc R U P A 1
C7 C 0.5508(19) 0.3950(17) 0.8518(9) 0.068(3) Uani 1 1 d . U . . .
C8 C 0.671(8) 0.390(6) 0.927(4) 0.12(3) Uani 0.40(3) 1 d D U P A 1
H8 H 0.7111 0.2907 0.9393 0.146 Uiso 0.40(3) 1 calc R U P A 1
C9 C 0.738(6) 0.537(6) 0.989(3) 0.089(13) Uani 0.40(3) 1 d D U P A 1
H9 H 0.8242 0.5404 1.0471 0.106 Uiso 0.40(3) 1 calc R U P A 1
C10 C 0.799(2) 0.4597(17) 0.7026(9) 0.074(4) Uani 1 1 d . . . . .
C11 C 0.679(2) 0.2751(17) 0.6544(10) 0.081(4) Uani 1 1 d . . . . .
H11 H 0.5506 0.2837 0.6143 0.098 Uiso 1 1 calc R U . . .
C12 C 0.789(3) 0.195(2) 0.5910(11) 0.098(5) Uani 1 1 d . . . . .
H12A H 0.9149 0.1824 0.6304 0.118 Uiso 1 1 calc R U . . .
H12B H 0.7097 0.0814 0.5615 0.118 Uiso 1 1 calc R U . . .
C13 C 0.836(3) 0.283(2) 0.5162(11) 0.095(5) Uani 1 1 d . . . . .
H13 H 0.9112 0.3987 0.5485 0.113 Uiso 1 1 calc R U . . .
C14 C 0.981(4) 0.208(2) 0.4673(16) 0.150(9) Uani 1 1 d . . . . .
H14A H 0.9184 0.1744 0.4009 0.224 Uiso 1 1 calc R U . . .
H14B H 1.0102 0.1111 0.4928 0.224 Uiso 1 1 calc R U . . .
H14C H 1.1033 0.2927 0.4779 0.224 Uiso 1 1 calc R U . . .
C15 C 0.665(4) 0.306(3) 0.4453(13) 0.138(8) Uani 1 1 d . . . . .
H15A H 0.5767 0.1976 0.4162 0.207 Uiso 1 1 calc R U . . .
H15B H 0.7130 0.3592 0.3983 0.207 Uiso 1 1 calc R U . . .
H15C H 0.5941 0.3775 0.4748 0.207 Uiso 1 1 calc R U . . .
C2A C 1.018(3) 0.982(3) 1.0742(17) 0.075(8) Uani 0.60(3) 1 d . . P A 2
H2A H 1.0563 0.8805 1.0935 0.090 Uiso 0.60(3) 1 calc R U P A 2
C3A C 0.833(3) 0.933(3) 0.9871(16) 0.060(6) Uani 0.60(3) 1 d . . P A 2
H3A H 0.7332 0.9987 0.9943 0.072 Uiso 0.60(3) 1 calc R U P A 2
C4A C 0.732(3) 0.740(2) 0.9446(15) 0.047(5) Uani 0.60(3) 1 d D U P A 2
C5A C 0.574(4) 0.703(3) 0.8621(17) 0.054(6) Uani 0.60(3) 1 d D U P A 2
H5A H 0.5299 0.7902 0.8352 0.065 Uiso 0.60(3) 1 calc R U P A 2
C6A C 0.484(5) 0.536(3) 0.821(2) 0.096(15) Uani 0.60(3) 1 d D U P A 2
H6A H 0.3714 0.5146 0.7699 0.115 Uiso 0.60(3) 1 calc R U P A 2
C8A C 0.699(3) 0.441(3) 0.9410(16) 0.051(5) Uani 0.60(3) 1 d D U P A 2
H8A H 0.7397 0.3552 0.9702 0.061 Uiso 0.60(3) 1 calc R U P A 2
C9A C 0.780(3) 0.604(3) 0.9843(17) 0.063(6) Uani 0.60(3) 1 d D U P A 2
H9A H 0.8727 0.6261 1.0429 0.076 Uiso 0.60(3) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O5 S1 O6 120.4(9) . .
O5 S1 N1 105.4(9) . .
O6 S1 N1 107.9(9) . .
O5 S1 C7 108.6(8) . .
O6 S1 C7 106.0(8) . .
N1 S1 C7 108.0(6) . .
C1 O1 H20 109.5 . .
C10 O3 H21 109.5 . .
C11 N1 S1 125.2(11) . .
C11 N1 H22 117.4 . .
S1 N1 H22 117.4 . .
O1 C1 O2 127.6(12) . .
O1 C1 C2A 115.2(14) . .
O2 C1 C2A 113.1(15) . .
O1 C1 C2 110.9(15) . .
O2 C1 C2 118.0(16) . .
C3 C2 C1 122(3) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C2 C3 C4 121(3) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C9 C4 C5 117(2) . .
C9 C4 C3 131(3) . .
C5 C4 C3 112(3) . .
C6 C5 C4 120(2) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C7 C6 C5 114(2) . .
C7 C6 H6 123.0 . .
C5 C6 H6 123.0 . .
C8 C7 C6 132(3) . .
C6A C7 C8A 112.7(17) . .
C8 C7 S1 110(2) . .
C6 C7 S1 117.9(16) . .
C6A C7 S1 120.9(14) . .
C8A C7 S1 126.2(13) . .
C7 C8 C9 115(3) . .
C7 C8 H8 122.6 . .
C9 C8 H8 122.6 . .
C8 C9 C4 122(3) . .
C8 C9 H9 118.8 . .
C4 C9 H9 118.8 . .
O4 C10 O3 125.5(13) . .
O4 C10 C11 118.9(12) . .
O3 C10 C11 115.3(12) . .
N1 C11 C12 112.7(13) . .
N1 C11 C10 111.8(11) . .
C12 C11 C10 110.1(13) . .
N1 C11 H11 107.3 . .
C12 C11 H11 107.3 . .
C10 C11 H11 107.3 . .
C13 C12 C11 117.7(14) . .
C13 C12 H12A 107.9 . .
C11 C12 H12A 107.9 . .
C13 C12 H12B 107.9 . .
C11 C12 H12B 107.9 . .
H12A C12 H12B 107.2 . .
C15 C13 C12 116.7(18) . .
C15 C13 C14 109.8(15) . .
C12 C13 C14 113.2(15) . .
C15 C13 H13 105.4 . .
C12 C13 H13 105.4 . .
C14 C13 H13 105.4 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C1 C2A C3A 114.0(17) . .
C1 C2A C3A 118.0(16) . 2_777
C3A C2A C3A 92.0(18) . 2_777
C1 C2A H2A 110.5 . .
C3A C2A H2A 110.5 . .
C3A C2A H2A 110.5 2_777 .
C2A C3A C4A 120.3(17) . .
C2A C3A C2A 88.0(18) . 2_777
C4A C3A C2A 112.3(16) . 2_777
C2A C3A H3A 111.4 . .
C4A C3A H3A 111.4 . .
C2A C3A H3A 111.4 2_777 .
C9A C4A C5A 117.2(16) . .
C9A C4A C3A 125.1(17) . .
C5A C4A C3A 117.6(15) . .
C6A C5A C4A 119.5(17) . .
C6A C5A H5A 120.2 . .
C4A C5A H5A 120.2 . .
C5A C6A C7 124(2) . .
C5A C6A H6A 117.8 . .
C7 C6A H6A 117.8 . .
C9A C8A C7 122.6(18) . .
C9A C8A H8A 118.7 . .
C7 C8A H8A 118.7 . .
C8A C9A C4A 122.5(18) . .
C8A C9A H9A 118.7 . .
C4A C9A H9A 118.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O5 1.425(14) .
S1 O6 1.436(12) .
S1 N1 1.596(15) .
S1 C7 1.741(15) .
O1 C1 1.233(15) .
O1 H20 0.8200 .
O2 C1 1.250(15) .
O3 C10 1.289(15) .
O3 H21 0.8200 .
O4 C10 1.241(15) .
N1 C11 1.429(17) .
N1 H22 0.8600 .
C1 C2A 1.51(3) .
C1 C2 1.66(4) .
C2 C3 1.32(4) .
C2 H2 0.9300 .
C3 C4 1.43(4) .
C3 H3 0.9300 .
C4 C9 1.40(3) .
C4 C5 1.40(2) .
C5 C6 1.37(2) .
C5 H5 0.9300 .
C6 C7 1.34(4) .
C6 H6 0.9300 .
C7 C8 1.25(5) .
C7 C6A 1.42(3) .
C7 C8A 1.43(3) .
C8 C9 1.34(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C11 1.560(18) .
C11 C12 1.51(2) .
C11 H11 0.9800 .
C12 C13 1.47(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C15 1.46(2) .
C13 C14 1.55(3) .
C13 H13 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C2A C3A 1.55(3) .
C2A C3A 1.66(4) 2_777
C2A H2A 0.9800 .
C3A C4A 1.57(3) .
C3A C2A 1.66(4) 2_777
C3A H3A 0.9800 .
C4A C9A 1.39(2) .
C4A C5A 1.40(2) .
C5A C6A 1.37(2) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
C8A C9A 1.35(3) .
C8A H8A 0.9300 .
C9A H9A 0.9300 .
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_4
O5 S1 N1 C11 180.0(12) . .
O6 S1 N1 C11 50.1(13) . .
C7 S1 N1 C11 -64.1(13) . .
O1 C1 C2 C3 169(3) . .
O2 C1 C2 C3 8(3) . .
C2A C1 C2 C3 -86(3) . .
C1 C2 C3 C4 172(3) . .
C2 C3 C4 C9 11(6) . .
C2 C3 C4 C5 -167(3) . .
C9 C4 C5 C6 -1(2) . .
C3 C4 C5 C6 178(3) . .
C4 C5 C6 C7 1(2) . .
C5 C6 C7 C8 -2(5) . .
C5 C6 C7 C6A -15(58) . .
C5 C6 C7 C8A -6(3) . .
C5 C6 C7 S1 179.4(14) . .
O5 S1 C7 C8 29(3) . .
O6 S1 C7 C8 159(3) . .
N1 S1 C7 C8 -85(3) . .
O5 S1 C7 C6 -153(2) . .
O6 S1 C7 C6 -22(2) . .
N1 S1 C7 C6 94(2) . .
O5 S1 C7 C6A -154(2) . .
O6 S1 C7 C6A -23(2) . .
N1 S1 C7 C6A 93(2) . .
O5 S1 C7 C8A 33.0(17) . .
O6 S1 C7 C8A 163.7(15) . .
N1 S1 C7 C8A -80.9(15) . .
C6 C7 C8 C9 3(7) . .
C6A C7 C8 C9 3(7) . .
C8A C7 C8 C9 14(8) . .
S1 C7 C8 C9 -179(3) . .
C7 C8 C9 C4 -2(6) . .
C5 C4 C9 C8 1(5) . .
C3 C4 C9 C8 -177(4) . .
S1 N1 C11 C12 -162.6(11) . .
S1 N1 C11 C10 72.8(16) . .
O4 C10 C11 N1 -136.8(15) . .
O3 C10 C11 N1 48.8(18) . .
O4 C10 C11 C12 97.1(16) . .
O3 C10 C11 C12 -77.3(16) . .
N1 C11 C12 C13 177.6(14) . .
C10 C11 C12 C13 -56.8(18) . .
C11 C12 C13 C15 -61(2) . .
C11 C12 C13 C14 169.8(15) . .
O1 C1 C2A C3A 161.4(17) . .
O2 C1 C2A C3A -39(2) . .
C2 C1 C2A C3A 67(2) . .
O1 C1 C2A C3A -92(2) . 2_777
O2 C1 C2A C3A 67(2) . 2_777
C2 C1 C2A C3A 174(3) . 2_777
C1 C2A C3A C4A -123.2(19) . .
C3A C2A C3A C4A 115(2) 2_777 .
C1 C2A C3A C2A 122(2) . 2_777
C3A C2A C3A C2A 0.000(1) 2_777 2_777
C2A C3A C4A C9A 7(3) . .
C2A C3A C4A C9A 108(2) 2_777 .
C2A C3A C4A C5A -176(2) . .
C2A C3A C4A C5A -75(2) 2_777 .
C9A C4A C5A C6A -4.1(18) . .
C3A C4A C5A C6A 178(2) . .
C4A C5A C6A C7 -6(3) . .
C8 C7 C6A C5A 15(5) . .
C6 C7 C6A C5A -178(100) . .
C8A C7 C6A C5A 11(4) . .
S1 C7 C6A C5A -163.0(18) . .
C8 C7 C8A C9A -179(12) . .
C6 C7 C8A C9A -8(3) . .
C6A C7 C8A C9A -7(3) . .
S1 C7 C8A C9A 166.5(17) . .
C7 C8A C9A C4A -2(3) . .
C5A C4A C9A C8A 8(3) . .
C3A C4A C9A C8A -175(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339237
