Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction
Maity, Soham; Dolui, Pravas; Kancherla, Rajesh; Maiti, Debabrata; Chem. Sci.  (2017) –; doi:10.1039/C7SC01204G

data_1546168
_publ_section_title
;
 Introducing unactivated acyclic internal aliphatic olefins into a cobalt
 catalyzed allylic selective dehydrogenative Heck reaction
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01204G
_journal_year                    2017
_chemical_formula_moiety         'C26 H30 F2 N2 O2'
_chemical_formula_sum            'C26 H30 F2 N2 O2'
_chemical_formula_weight         440.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2016-09-29 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                96.816(4)
_cell_angle_beta                 105.872(5)
_cell_angle_gamma                103.544(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4306(4)
_cell_length_b                   11.7839(6)
_cell_length_c                   12.6627(6)
_cell_measurement_reflns_used    5313
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.8260
_cell_measurement_theta_min      1.8840
_cell_volume                     1153.69(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00-180.00  360
  2  \w    -76.50  19.00   0.50    8.00    --  -20.00 -72.00-180.00  191
  3  \w    -75.50  10.00   0.50    8.00    --  -20.00 -72.00 -36.00  171
  4  \w    -51.50   0.00   0.50    8.00    --  -20.00  72.00 108.00  103
  5  \w    -98.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  234
  6  \w    -92.50 -24.00   0.50    8.00    --  -20.00 -72.00 108.00  137
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147300000
_diffrn_orient_matrix_UB_12      0.0366340000
_diffrn_orient_matrix_UB_13      0.0428910000
_diffrn_orient_matrix_UB_21      -0.0081479000
_diffrn_orient_matrix_UB_22      0.0431907000
_diffrn_orient_matrix_UB_23      -0.0341489000
_diffrn_orient_matrix_UB_31      -0.0895217000
_diffrn_orient_matrix_UB_32      -0.0278931000
_diffrn_orient_matrix_UB_33      -0.0228067000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.891
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13034
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.705
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1415P)^2^+0.6235P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2889
_reflns_number_total             4046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01204g2.cif
_cod_data_source_block           dm-aqd-364-a-p_mo
_cod_original_cell_volume        1153.70(11)
_cod_database_code               1546168
_shelxl_version_number           2012-9
_reflns_odcompleteness_completeness 90.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.16
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C8(H8A,H8B), C0AA(H0AA,H0AB), C25(H25A,H25B), C9(H9A,H9B),
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C19(H19), C22(H22), C14(H14), C21(H21), C20(H20), C13(H13),
 C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              9597
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.657