Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines
David R Chisholm; Garr-Layy Zhou; Ehmke Pohl; Roy Valentine; Andrew Whiting; Beilstein Journal of Organic Chemistry 12 (2016) 1851–1862; doi:10.3762/bjoc.12.174

data_4033355
_publ_section_title
;
 Practical synthetic strategies towards lipophilic
 6-iodotetrahydroquinolines and -dihydroquinolines
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1851
_journal_page_last               1862
_journal_paper_doi               10.3762/bjoc.12.174
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C20 H32 B N O2'
_chemical_formula_sum            'C20 H32 B N O2'
_chemical_formula_weight         329.27
_chemical_name_systematic
4,4-Dimethyl-1-(propan-2-yl)-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.039(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0435(6)
_cell_length_b                   11.5154(6)
_cell_length_c                   28.6939(14)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.27
_cell_volume                     3957.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            70443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.907
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.9287.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       'Miyaura borylation'
_exptl_crystal_recrystallization_method
'Recrystallised from hexane by solvent evaporation'
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         9094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0600
_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^)+(0.0574P)^2^+2.7605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6489
_reflns_number_total             9094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            29_1433622.cif
_cod_data_source_block           mo_dc350_0m
_cod_database_code               4033355
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.979
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C35(H35A,H35B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C27(H27), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C38(H38A,H38B,H38C),
 C39(H39A,H39B,H39C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              58259
_shelx_hkl_checksum              18163
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'Mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id DC350
_olex2_submission_special_instructions 'No special instructions were received'