Asymmetric Catalytic Insertion of α-Diazo Carbonyl Compounds into O–H Bonds of Carboxylic Acids
Tan, Fei; Liu, Xiaohua; Hao, Xiaoyu; Tang, Yu; Lin, Lili; Feng, Xiaoming; ACS Catalysis  (2016) 6930–; doi:10.1021/acscatal.6b02184

data_4513958
_publ_section_title
;
 Asymmetric Catalytic Insertion of \a-Diazo Carbonyl Compounds into O--H
 Bonds of Carboxylic Acids
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              6930
_journal_paper_doi               10.1021/acscatal.6b02184
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H15 Br O4 S'
_chemical_formula_sum            'C16 H15 Br O4 S'
_chemical_formula_weight         383.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.929(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8773(8)
_cell_length_b                   7.1193(4)
_cell_length_c                   14.0576(11)
_cell_measurement_reflns_used    1075
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.7300
_cell_measurement_theta_min      3.3250
_cell_volume                     862.32(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -10.00   18.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 28

  2 omega  -55.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  -30.0000 98

  3 omega    4.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  150.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0623012000
_diffrn_orient_matrix_UB_12      0.0315801000
_diffrn_orient_matrix_UB_13      -0.0193884000
_diffrn_orient_matrix_UB_21      -0.0499887000
_diffrn_orient_matrix_UB_22      0.0019485000
_diffrn_orient_matrix_UB_23      -0.0476705000
_diffrn_orient_matrix_UB_31      -0.0197219000
_diffrn_orient_matrix_UB_32      0.0944807000
_diffrn_orient_matrix_UB_33      0.0074766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3903
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0207P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                2342
_reflns_number_total             2975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b02184_si_002.cif
_cod_data_source_block           150520_s1_tf_m
_cod_original_cell_volume        862.32(11)
_cod_database_code               4513958
_chemical_oxdiff_formula         c15h25o4br1s1
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'