Chemodivergent, Tunable, and Selective Iodine(III)-Mediated Bromo-Functionalizations of Polyprenoids.
Grayfer, Tatyana D.; Retailleau, Pascal; Dodd, Robert H.; Dubois, Joëlle; Cariou, Kevin; Organic letters 19 (2017) 4766–4769; doi:10.1021/acs.orglett.7b02125

data_1547574
_publ_section_title
;
 Chemodivergent, Tunable, and Selective Iodine(III)-Mediated
 Bromo-Functionalizations of Polyprenoids.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4766
_journal_page_last               4769
_journal_paper_doi               10.1021/acs.orglett.7b02125
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C16 H21 Br'
_chemical_formula_sum            'C16 H21 Br'
_chemical_formula_weight         293.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   direct
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_cell_length_a                   19.772(2)
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0820
_cell_measurement_theta_min      3.4430
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_diffrn_detector                 'Dectris HPAD PILATUS3R 200 K'
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator
'Rigaku double bounce MaxFlux multilayer optics'
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_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19424
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.749
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       'flat needle'
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0310P)^2^+5.6387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2147
_reflns_number_total             3977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02125_si_002.cif
_cod_data_source_block           compound_5d
_cod_original_cell_volume        2865.6(5)
_cod_database_code               1547574
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              36401
_shelx_hkl_checksum              70200