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_1550413
_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 unk
_chemical_compound_source        'Titouan Royal'
_chemical_formula_moiety         'C24 H22 F N O4'
_chemical_formula_sum            'C24 H22 F N O4'
_chemical_formula_weight         407.44
_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_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-09
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.0660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3747(2)
_cell_length_b                   7.24010(10)
_cell_length_c                   18.6840(3)
_cell_measurement_reflns_used    89515
_cell_measurement_temperature    130
_cell_measurement_theta_max      57.46
_cell_measurement_theta_min      2.56
_cell_volume                     2033.85(5)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      130
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.9705
_diffrn_measured_fraction_theta_max 0.9705
_diffrn_measurement_details      ' 6288 frames, detector distance = 60 mm'
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41456
_diffrn_reflns_theta_full        57.0832
_diffrn_reflns_theta_max         57.08
_diffrn_reflns_theta_min         2.56
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_source_voltage           70
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  0.9497
_exptl_absorpt_correction_T_min  0.3571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.3305
_exptl_crystal_description       Plate
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
; 
cyclohexane
;
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.1677
_refine_diff_density_min         -0.3316
_refine_diff_density_rms         0.0451
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_d_res_high            0.7990
_refine_ls_d_res_low             15.0350
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0474
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    78
_refine_ls_number_parameters     544
_refine_ls_number_reflns         8088
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0474
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0802P)^2^+0.3205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.947
_reflns_limit_h_max              19
_reflns_limit_h_min              -18
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                7479
_reflns_number_total             8088
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8sc05058a2.cif
_cod_data_source_block           TIT1533F11-15_130K
_cod_database_code               1550413
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C43(H43), C45(H45)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31a,H31b), C46(H46a,H46b), C54(H54a,H54b), C50(H50a,H50b), C55(H55a,
 H55b), C59(H59a,H59b)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C24(H24), C26(H26), C27(H27), C35(H35), C38(H38),
 C39(H39), C51(H51), C52(H52), C57(H57), C58(H58), C14(H14), C15(H15), C28(H28),
  C29(H29), C33(H33), C34(H34), C36(H36), C37(H37), C40(H40), C48(H48),
 C53(H53), C56(H56)
2.d Idealised Me refined as rotating group:
 C49(H49a,H49b,H49c), C60(H60a,H60b,H60c)
;
_olex2_submission_special_instructions 'No special instructions were received'