Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes.
Tripathi, Chandra Bhushan; Mukherjee, Santanu; Organic letters 17 (2015) 4424–4427; doi:10.1021/acs.orglett.5b02026

data_1534111
_publ_section_title
;
 Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated
 Dienes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4424
_journal_page_last               4427
_journal_paper_doi               10.1021/acs.orglett.5b02026
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 I N O'
_chemical_formula_sum            'C18 H16 I N O'
_chemical_formula_weight         389.22
_chemical_name_systematic        CBT-V-255-01
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.817(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9179(15)
_cell_length_b                   5.7432(7)
_cell_length_c                   14.186(2)
_cell_measurement_reflns_used    2184
_cell_measurement_temperature    298
_cell_volume                     803.88(19)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13227
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0814 after correction.
The Ratio of minimum to maximum transmission is 0.7803.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.0250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1909
_reflns_number_total             3516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02026_si_003.cif
_cod_data_source_block           ent-3a
_cod_original_cell_volume        803.9(2)
_cod_database_code               1534111
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Rigid bond restraints
 C4, C3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2A, C3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C3A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C2A \\sim C3A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C1 \\sim C2A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C4 \\sim C3: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C2 \\sim C3: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C1 \\sim C2: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Same fragment restrains
{C3, C2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C3A, C2A}
5. Others
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(H1BC)=Sof(H1BD)=1-FVAR(1)
 Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1(H1AA,H1AB), C1(H1BC,H1BD)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C3A(H3A), C2A(H2A), C9(H9), C16(H16), C15(H15), C14(H14),
 C8(H8), C10(H10), C17(H17), C18(H18), C12(H12), C11(H11)
;
_olex2_submission_original_sample_id CBT-V-255-01
_olex2_submission_special_instructions 'No special instructions were received'