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_4513977
_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 ad
_chemical_formula_moiety         'C16 H15 Br O2'
_chemical_formula_sum            'C16 H15 Br O2'
_chemical_formula_weight         319.19
_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
_audit_creation_date             2015-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.560(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8973(3)
_cell_length_b                   6.9477(3)
_cell_length_c                   12.2822(5)
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    293.28(10)
_cell_measurement_theta_max      72.7010
_cell_measurement_theta_min      5.1000
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_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
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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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
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_diffrn_measured_fraction_theta_full 0.999
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_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  120.0000 67

  2 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   30.0000 101

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  150.0000 74

  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

  7 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

  8 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -30.0000 94

  9 omega   40.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 95

 10 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 11 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   91.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 13 omega   40.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

 14 omega   38.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 15 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 16 omega   38.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 17 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

 18 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 19 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 20 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 21 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 85

 22 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 78

 23 omega   91.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 24 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -150.0000 88

 25 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   30.0000 88

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94

 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

 28 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  150.0000 84

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

 30 omega   70.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
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_diffrn_orient_matrix_UB_11      0.0792101000
_diffrn_orient_matrix_UB_12      0.1906578000
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_diffrn_orient_matrix_UB_21      0.1573117000
_diffrn_orient_matrix_UB_22      -0.0954742000
_diffrn_orient_matrix_UB_23      0.0372468000
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_diffrn_orient_matrix_UB_33      -0.1204167000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0293
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7922
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_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         5.676
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57390
_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_colour            'clear light colourless'
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_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description
;
;
_exptl_crystal_F_000             324
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;
 Flack x determined using 1134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(14)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_restrained_S_all      1.083
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1346P)^2^+0.3376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            cs6b02048_si_003.cif
_cod_data_source_block           fxm-zpf-stan
_cod_depositor_comments
'Adding full bibliography for 4513975--4513977.cif.'
_cod_database_code               4513977
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C16(H16), C19(H19), C25(H25), C28(H28), C2(H2), C5(H5), C6(H6),
 C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              66019
_shelx_hkl_checksum              3402
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-24
_olex2_submission_special_instructions 'No special instructions were received'