Chiral dirhodium catalysts derived from l-serine, l-threonine and l-cysteine: design, synthesis and application
Kang, Jian; Zhu, Baofu; Liu, Jiewei; Wang, Bo; Zhang, Li; Su, Cheng-Yong; Organic Chemistry Frontiers 2 (2015) 890–; doi:10.1039/C5QO00110B

data_1553134
_publ_section_title
;
 Chiral dirhodium catalysts derived from l-serine, l-threonine and
 l-cysteine: design, synthesis and application
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              890
_journal_paper_doi               10.1039/C5QO00110B
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H13 N O7 S2'
_chemical_formula_sum            'C11 H13 N O7 S2'
_chemical_formula_weight         335.34
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-12-08 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.82043(19)
_cell_length_b                   10.2265(3)
_cell_length_c                   17.4910(4)
_cell_measurement_reflns_used    4007
_cell_measurement_temperature    299.0(4)
_cell_measurement_theta_max      62.2370
_cell_measurement_theta_min      4.9890
_cell_volume                     1398.85(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.0(4)
_diffrn_detector_area_resol_mean 8.0428
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -106.00  -72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2729 -179.0000   60.0000 34

  2 omega   43.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   57.0000 -180.0000 56

  3 omega  -36.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729  -37.0000    0.0000 96

  4 omega   35.00   81.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000  -90.0000 46

  5 omega   79.00  133.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  111.0000    0.0000 54

  6 omega   20.00   66.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000 -150.0000 46

  7 omega  115.00  162.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000   60.0000 47

  8 omega   32.00   69.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000  -90.0000 37

  9 omega   46.00   73.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -45.0000 -180.0000 27

 10 omega   19.00   70.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000 -120.0000 51

 11 omega  108.00  134.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500   77.0000    0.0000 26

 12 omega   30.00   60.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000   30.0000 30

 13 omega   97.00  123.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  111.0000  -60.0000 26

 14 omega   56.00   96.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000   30.0000 40

 15 omega  101.00  127.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000   30.0000 26

 16 omega   82.00  109.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000  -90.0000 27

 17 omega   42.00   76.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -45.0000  120.0000 34

 18 omega   83.00  158.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000  120.0000 75

 19 omega -110.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2729 -179.0000 -150.0000 54

 20 omega    4.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   77.0000  -90.0000 100

 21 omega   14.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   57.0000  120.0000 89

 22 omega    4.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   77.0000    0.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0170035000
_diffrn_orient_matrix_UB_12      0.1288467000
_diffrn_orient_matrix_UB_13      -0.0449786000
_diffrn_orient_matrix_UB_21      -0.1817305000
_diffrn_orient_matrix_UB_22      -0.0188372000
_diffrn_orient_matrix_UB_23      -0.0321398000
_diffrn_orient_matrix_UB_31      -0.0740610000
_diffrn_orient_matrix_UB_32      0.0757459000
_diffrn_orient_matrix_UB_33      0.0685759000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6590
_diffrn_reflns_theta_full        62.51
_diffrn_reflns_theta_max         62.51
_diffrn_reflns_theta_min         5.01
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0355
_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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2081
_reflns_number_total             2188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00110b2.cif
_cod_data_source_block           3
_cod_original_cell_volume        1398.86(6)
_cod_database_code               1553134
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6a), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'