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_4033357
_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         'C11 H12 I N O'
_chemical_formula_sum            'C11 H12 I N O'
_chemical_formula_weight         301.12
_chemical_name_systematic
6-Iodo-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 126.024(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7230(4)
_cell_length_b                   8.16224(10)
_cell_length_c                   17.8772(4)
_cell_measurement_reflns_used    33824
_cell_measurement_temperature    120
_cell_measurement_theta_max      37.5910
_cell_measurement_theta_min      2.1770
_cell_volume                     2209.58(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega   10.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   77.0000 -180.0000 97

  2 omega  -31.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  -77.0000   60.0000 98

  3 omega    0.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   19.0000 -180.0000 111

  4 omega -112.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  178.0000  120.0000 80

  5 omega    3.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   90.0000  -94.8721 34

  6 omega   20.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   57.0000  -60.0000 87

  7 omega   -3.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  101.0000   21.8822 26

  8 omega   35.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  178.0000   60.0000 77

  9 omega   16.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   38.0000   30.0000 93

 10 omega -106.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -57.0000   60.0000 87

 11 omega  -66.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213   77.0000   60.0000 98

 12 omega -112.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  178.0000 -180.0000 80

 13 omega -106.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -57.0000    0.0000 87

 14 omega   -4.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  102.0000  174.2607 27

 15 omega   35.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  178.0000 -120.0000 77

 16 omega -106.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -57.0000  150.0000 87

 17 omega  -87.00   10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  117.0000  164.0000 97

 18 omega -107.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -77.0000  -60.0000 98

 19 omega   16.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   38.0000  -90.0000 93

 20 omega  -24.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588 -100.0000   30.0000 103

 21 omega   10.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   77.0000  120.0000 97

 22 omega -107.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -77.0000 -150.0000 98

 23 omega -106.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -57.0000 -150.0000 87

 24 omega   35.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  178.0000    0.0000 77

 25 omega   10.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   77.0000  -30.0000 97

 26 omega   10.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588   77.0000   30.0000 97

 27 omega  -32.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2588  -38.0000  120.0000 93

 28 omega -107.00  -76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -77.0000  120.0000 31

 29 omega -106.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.3213  -57.0000  -30.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0229831000
_diffrn_orient_matrix_UB_12      -0.0439601000
_diffrn_orient_matrix_UB_13      0.0139967000
_diffrn_orient_matrix_UB_21      -0.0200705000
_diffrn_orient_matrix_UB_22      0.0737919000
_diffrn_orient_matrix_UB_23      -0.0000936000
_diffrn_orient_matrix_UB_31      -0.0355418000
_diffrn_orient_matrix_UB_32      -0.0132537000
_diffrn_orient_matrix_UB_33      -0.0470045000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            90313
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         37.821
_diffrn_reflns_theta_min         2.502
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           35
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.609
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'The material was recrystallised from EtOAc by slow evaporation'
_exptl_crystal_size_max          0.5211
_exptl_crystal_size_mid          0.3649
_exptl_crystal_size_min          0.2118
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0190
_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^)+(0.0215P)^2^+1.5131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0486
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5216
_reflns_number_total             5817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            19_1433617.cif
_cod_data_source_block           dc248
_cod_original_cell_volume        2209.57(11)
_cod_database_code               4033357
_chemical_oxdiff_formula         'C11 H12 I N O'
_reflns_odcompleteness_completeness 99.96
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              53706
_shelx_hkl_checksum              61638
_olex2_date_sample_data_collection 2015-04-29
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700 Series'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id DC248
_olex2_submission_special_instructions 'No special instructions were received'