Catalytic Asymmetric Intra- and Intermolecular Haloetherification of Enones: An Efficient Approach to (−)-Centrolobine
Zhou, Pengfei; Cai, Yunfei; Zhong, Xia; Luo, Weiwei; Kang, Tengfei; Li, Jun; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; ACS Catalysis 6 (2016) 7778–; doi:10.1021/acscatal.6b02048

data_4513975
_publ_section_title
;
 Catalytic Asymmetric Intra- and Intermolecular Haloetherification of
 Enones: An Efficient Approach to (&#x2212;)-Centrolobine
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7778
_journal_paper_doi               10.1021/acscatal.6b02048
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C11 H13 Br O2 S'
_chemical_formula_sum            'C11 H13 Br O2 S'
_chemical_formula_weight         289.18
_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
_audit_creation_date             2015-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.113(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6991(8)
_cell_length_b                   9.5870(7)
_cell_length_c                   13.7942(13)
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.2070
_cell_measurement_theta_min      3.6470
_cell_volume                     1238.29(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -53.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819  -38.0000   60.0000 88

  2 omega  -20.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819  -99.0000   30.0000 75

  3 omega  -11.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819   77.0000  -30.0000 94

  4 omega   -1.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819   57.0000 -150.0000 84

  5 omega   -1.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819   57.0000 -120.0000 84

  6 omega  -62.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8194  110.0000   39.0000 51

  7 omega   -3.00   37.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819   38.0000  150.0000 40

  8 omega  -51.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8819  -57.0000 -150.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0361198000
_diffrn_orient_matrix_UB_12      -0.0079160000
_diffrn_orient_matrix_UB_13      -0.0514731000
_diffrn_orient_matrix_UB_21      -0.0058675000
_diffrn_orient_matrix_UB_22      -0.0727744000
_diffrn_orient_matrix_UB_23      0.0072800000
_diffrn_orient_matrix_UB_31      -0.0663890000
_diffrn_orient_matrix_UB_32      0.0106954000
_diffrn_orient_matrix_UB_33      0.0114717000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14793
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description
;
;
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4999
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3271
_reflns_number_total             4999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02048_si_002.cif
_cod_data_source_block           fxm-zpf-20150326
_cod_depositor_comments
'Adding full bibliography for 4513975--4513977.cif.'
_cod_original_cell_volume        1238.31(19)
_cod_database_code               4513975
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00N), C00D(H00D), C00F(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00C), C00M(H00Q,H00R), C00O(H00E,H00F), C00P(H00H,H00K), C00Q(H00L,
 H00M), C00S(H00U,H00V), C00T(H00W,H00X), C00U(H00Y,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00P), C00N(H00S), C00R(H00T)
;
_shelx_res_checksum              11464
_shelx_hkl_checksum              36573
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 1427426327.72
_olex2_submission_special_instructions 'No special instructions were received'