Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
Royal, Titouan; Baudoin, Olivier; Chemical Science  (2019) –; doi:10.1039/C8SC05058A

data_1550414
_publ_section_title
;
 Pd-catalyzed \g-arylation of \g,\d-unsaturated O-carbamates via an
 unusual haptotropic rearrangement
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05058A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'T. Royal'
_chemical_formula_moiety         'C24 H22 F1 N1 O4'
_chemical_formula_sum            'C24 H22 F N O4'
_chemical_formula_weight         407.44
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-12-13
_audit_creation_method           CRYSTALS_ver_14.61_build_7031
_audit_update_record
;
2018-12-13 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1332(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3844(8)
_cell_length_b                   7.2248(4)
_cell_length_c                   18.6689(10)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    130
_cell_measurement_theta_max      70
_cell_measurement_theta_min      3
_cell_volume                     2028.68(19)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.037
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27443
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.141
_diffrn_reflns_theta_min         4.183
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.57
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
; 
Cyclohexane
;
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 3286 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8837
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7435
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.0002956
_refine_ls_shift/su_mean         0.0000201
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.58P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0884
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0884
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                7304
_reflns_number_total             7436
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0356
_oxford_refine_ls_scale          0.12351(3)
_oxford_reflns_number_all        7435
_oxford_structure_analysis_title 'TIT1533F25_130K_0m in P2(1)'
_cod_data_source_file            c8sc05058a2.cif
_cod_data_source_block           TIT1533F25_130K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C24 H22 F1 N1 O4'
_cod_database_code               1550414
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.03(3)
_oxford_bijvoet_difference       0.04(2)
_oxford_refined_flack_x          0.02(11)