#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502204.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_1502204
loop_
_publ_author_name
'Churches, Quentin I.'
'White, Jonathan M.'
'Hutton, Craig A.'
_publ_section_title
;
 Synthesis of β,γ-dihydroxyhomotyrosines by a tandem Petasis-asymmetric
 dihydroxylation approach.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2900
_journal_page_last               2903
_journal_paper_doi               10.1021/ol200917s
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C15 H21 N O4 S'
_chemical_formula_weight         311.39
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8864(2)
_cell_length_b                   13.4539(4)
_cell_length_c                   20.4973(6)
_cell_measurement_reflns_used    3378
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.1017
_cell_measurement_theta_min      3.2814
_cell_volume                     1623.28(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.846
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3306
_diffrn_reflns_theta_full        69.96
_diffrn_reflns_theta_max         69.96
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    1.903
_exptl_absorpt_correction_T_max  0.534
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.6639
_exptl_crystal_size_mid          0.5729
_exptl_crystal_size_min          0.4215
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0350
_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)+(0.0658P)²+0.4899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                2104
_reflns_number_total             2139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200917s_si_002.cif
_cod_data_source_block           jmwqc4
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1502204
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C1 C 0.3930(4) 1.22081(15) 1.03276(11) 0.0189(5) Uani 1 1 d .
C2 C 0.3548(5) 1.10801(15) 1.03655(10) 0.0199(5) Uani 1 1 d .
H2 H 0.2129 1.0956 1.0602 0.024 Uiso 1 1 calc R
C3 C 0.5439(4) 1.05513(15) 1.07099(11) 0.0220(5) Uani 1 1 d .
H3 H 0.6861 1.0542 1.0513 0.026 Uiso 1 1 calc R
C4 C 0.5203(5) 1.00951(16) 1.12805(11) 0.0223(5) Uani 1 1 d .
H4 H 0.3809 1.0170 1.1489 0.027 Uiso 1 1 calc R
C5 C 0.6896(4) 0.94883(15) 1.16162(11) 0.0205(5) Uani 1 1 d .
C6 C 0.8971(5) 0.92265(15) 1.13389(10) 0.0234(5) Uani 1 1 d .
H6 H 0.9343 0.9473 1.0929 0.028 Uiso 1 1 calc R
C7 C 1.0495(5) 0.86113(16) 1.16552(12) 0.0255(6) Uani 1 1 d .
H7 H 1.1870 0.8448 1.1459 0.031 Uiso 1 1 calc R
C8 C 0.9955(5) 0.82344(16) 1.22736(11) 0.0244(6) Uani 1 1 d .
C9 C 0.7930(5) 0.84812(18) 1.25613(11) 0.0290(6) Uani 1 1 d .
H9 H 0.7562 0.8231 1.2971 0.035 Uiso 1 1 calc R
C10 C 0.6426(5) 0.91086(17) 1.22364(11) 0.0254(6) Uani 1 1 d .
H10 H 0.5066 0.9280 1.2438 0.030 Uiso 1 1 calc R
C11 C 1.1068(7) 0.7191(2) 1.31554(13) 0.0438(8) Uani 1 1 d .
H11A H 1.2310 0.6776 1.3290 0.066 Uiso 1 1 calc R
H11B H 0.9710 0.6799 1.3124 0.066 Uiso 1 1 calc R
H11C H 1.0849 0.7711 1.3470 0.066 Uiso 1 1 calc R
C12 C 0.2537(5) 0.90222(17) 0.90240(12) 0.0262(6) Uani 1 1 d .
C13 C 0.3892(6) 0.9476(2) 0.84750(13) 0.0440(7) Uani 1 1 d .
H13A H 0.2888 0.9827 0.8187 0.066 Uiso 1 1 calc R
H13B H 0.4657 0.8960 0.8238 0.066 Uiso 1 1 calc R
H13C H 0.4992 0.9929 0.8651 0.066 Uiso 1 1 calc R
C14 C 0.0582(6) 0.83790(19) 0.87714(16) 0.0406(7) Uani 1 1 d .
H14A H -0.0322 0.8758 0.8471 0.061 Uiso 1 1 calc R
H14B H -0.0345 0.8170 0.9131 0.061 Uiso 1 1 calc R
H14C H 0.1186 0.7806 0.8553 0.061 Uiso 1 1 calc R
C15 C 0.3996(7) 0.8446(2) 0.95024(15) 0.0490(9) Uani 1 1 d .
H15A H 0.5215 0.8861 0.9653 0.074 Uiso 1 1 calc R
H15B H 0.4612 0.7870 0.9290 0.074 Uiso 1 1 calc R
H15C H 0.3086 0.8243 0.9867 0.074 Uiso 1 1 calc R
N1 N 0.3316(4) 1.06905(13) 0.97029(9) 0.0244(5) Uani 1 1 d .
H1 H 0.4321 1.0830 0.9412 0.029 Uiso 1 1 calc R
O1 O 0.3970(4) 1.25905(12) 1.09193(8) 0.0272(4) Uani 1 1 d .
O2 O 0.4166(3) 1.26535(11) 0.98249(7) 0.0229(4) Uani 1 1 d .
O3 O -0.0370(4) 1.05182(14) 0.90415(11) 0.0502(7) Uani 1 1 d .
O4 O 1.1567(4) 0.76176(12) 1.25344(9) 0.0339(5) Uani 1 1 d .
S S 0.11458(11) 0.99892(4) 0.95159(2) 0.02416(17) Uani 1 1 d .
H H 0.417(6) 1.316(2) 1.0866(15) 0.040(9) 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 0.0181 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
O2 C1 O1 126.39(19)
O2 C1 C2 123.6(2)
O1 C1 C2 109.99(18)
N1 C2 C3 109.7(2)
N1 C2 C1 108.71(17)
C3 C2 C1 112.6(2)
C4 C3 C2 123.8(2)
C3 C4 C5 127.0(2)
C6 C5 C10 116.9(2)
C6 C5 C4 123.2(2)
C10 C5 C4 119.8(2)
C7 C6 C5 122.0(2)
C6 C7 C8 119.6(3)
O4 C8 C9 125.5(2)
O4 C8 C7 114.5(3)
C9 C8 C7 119.9(2)
C8 C9 C10 119.6(2)
C9 C10 C5 122.0(2)
C13 C12 C15 112.9(3)
C13 C12 C14 112.0(2)
C15 C12 C14 110.8(2)
C13 C12 S 111.00(18)
C15 C12 S 105.03(17)
C14 C12 S 104.51(18)
C2 N1 S 119.86(18)
C8 O4 C11 116.7(2)
O3 S N1 110.08(12)
O3 S C12 104.20(12)
N1 S C12 100.89(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.200(3)
C1 O1 1.318(3)
C1 C2 1.536(3)
C2 N1 1.462(3)
C2 C3 1.498(3)
C3 C4 1.328(3)
C4 C5 1.461(3)
C5 C6 1.393(4)
C5 C10 1.398(3)
C6 C7 1.382(4)
C7 C8 1.402(3)
C8 O4 1.369(3)
C8 C9 1.371(4)
C9 C10 1.393(4)
C11 O4 1.427(3)
C12 C13 1.508(4)
C12 C15 1.517(4)
C12 C14 1.530(4)
C12 S 1.838(2)
N1 S 1.634(2)
O3 S 1.499(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53341834
