Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities
Li, Jing; Li, Zequan; Zhang, Xun; Xu, Bing; Shi, Yian; Organic Chemistry Frontiers 4 (2017) 1084–; doi:10.1039/C6QO00636A

data_1553578
_publ_section_title
;
 Catalytic enantioselective bromohydroxylation of aryl olefins with
 flexible functionalities
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1084
_journal_paper_doi               10.1039/C6QO00636A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H14 Br F O2'
_chemical_formula_sum            'C11 H14 Br F O2'
_chemical_formula_weight         277.13
_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
_audit_creation_date             2015-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-28 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   5.651(2)
_cell_length_b                   16.364(7)
_cell_length_c                   38.4918(16)
_cell_measurement_reflns_used    8474
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      28.3284
_cell_measurement_theta_min      1.3522
_cell_volume                     3559(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 55.2601
	          2theta: -20.0349
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 55.2601
	          2theta: -20.0349
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 55.2601
	          2theta: -20.0349
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0088
_diffrn_orient_matrix_UB_12      0.0422
_diffrn_orient_matrix_UB_13      0.1716
_diffrn_orient_matrix_UB_21      -0.0528
_diffrn_orient_matrix_UB_22      0.0291
_diffrn_orient_matrix_UB_23      -0.0099
_diffrn_orient_matrix_UB_31      -0.0130
_diffrn_orient_matrix_UB_32      -0.0220
_diffrn_orient_matrix_UB_33      0.0047
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            34787
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.400
_diffrn_reflns_theta_min         1.352
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    3.456
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       rod
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Flack x determined using 2004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0055P)^2^+10.0141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6977
_reflns_number_total             7939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00636a2.cif
_cod_data_source_block           mx4298
_cod_database_code               1553578
_diffrn_number_total             4653
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C2B(H2BB,H2BC), C3B(H3BA,H3BB), C2A(H2AB,H2AC),
 C3A(H3AA,H3AB)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C5B(H5B), C9B(H9B), C5A(H5A), C9A(H9A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C10B(H10D,H10E,H10F), C11B(H11D,
 H11E,H11F), C10A(H10G,H10H,H10I), C11A(H11G,H11H,H11I)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1B(H1B), O2B(H2BA), O1A(H1A), O2A(H2AA)
;
_shelx_res_checksum              24607
_shelx_hkl_checksum              49615
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'