NHC-catalyzed Truce-Smiles rearrangement of <i>N</i>-aryl methacrylamides for the synthesis of <i>trans</i>-cinnamides.
Hu, Yuanyuan; Wang, Zhen; Luo, Honggen; Jin, Hongwei; Liu, Yunkui; Zhou, Bingwei; Organic & biomolecular chemistry 19 (2021) 3834–3837; doi:10.1039/d1ob00443c

data_7158003
_publ_section_title
;
 NHC-catalyzed Truce-Smiles rearrangement of <i>N</i>-aryl methacrylamides
 for the synthesis of <i>trans</i>-cinnamides.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3834
_journal_page_last               3837
_journal_paper_doi               10.1039/d1ob00443c
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C11 H11 Br Cl N O'
_chemical_formula_sum            'C11 H11 Br Cl N O'
_chemical_formula_weight         288.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7336(5)
_cell_length_b                   9.4426(5)
_cell_length_c                   12.9051(8)
_cell_measurement_reflns_used    4662
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.868
_cell_measurement_theta_min      2.980
_cell_volume                     1186.11(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5057
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.844
_diffrn_reflns_theta_min         5.679
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.460
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1265 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.6405. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.2396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.657
_reflns_number_gt                1823
_reflns_number_total             1866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00443c2.cif
_cod_data_source_block           2010167490
_cod_depositor_comments          'Adding full bibliography for 7158003.cif.'
_cod_database_code               7158003
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.776
_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:
 N1(H1), C2(H2), C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              9506
_olex2_submission_special_instructions 'No special instructions were received'