Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring.
Chisholm, David R.; Valentine, Roy; Pohl, Ehmke; Whiting, Andrew; The Journal of organic chemistry 81 (2016) 7557–7565; doi:10.1021/acs.joc.6b01110

data_4036976
_publ_section_title
;
 Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene
 Geometric Insights through In Situ FTIR Monitoring.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7557
_journal_page_last               7565
_journal_paper_doi               10.1021/acs.joc.6b01110
_journal_volume                  81
_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
(3Z)-4-[(4-iodo-2-methylphenyl)amino]but-3-en-2-one
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.061(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0960(9)
_cell_length_b                   11.3400(8)
_cell_length_c                   7.9095(6)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    120
_cell_measurement_theta_max      33.23
_cell_measurement_theta_min      2.46
_cell_volume                     1084.23(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f 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  0.0636
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18377
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.233
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.920
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1429 before and 0.1054 after correction.
The Ratio of minimum to maximum transmission is 0.3919.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'The material was recrystallised from EtOAc by slow evaporation'
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.042
_refine_diff_density_max         5.045
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1394P)^2^+0.1298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3573
_reflns_number_total             4161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01110_si_002.cif
_cod_data_source_block           mo_dc210face
_cod_database_code               4036976
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              93849
_shelx_hkl_checksum              47949
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id DC210
_olex2_submission_special_instructions 'No special instructions were received'