Orthogonal Selectivity in C‒H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution
Agasti, Soumitra; Mondal, Bhaskar; Achar, Tapas Kumar; Sinha, Soumya Kumar; Sarala Suseelan, Anjana; Szabo, Kalman J.; Schoenebeck, Franziska; Maiti, Debabrata; ACS Catalysis 9 (2019) 9606–; doi:10.1021/acscatal.9b03019

data_4514617
_publ_section_title
;
 Orthogonal Selectivity in C--H Olefination: Synthesis of Branched
 Vinylarene with Unactivated Aliphatic Substitution
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9606
_journal_paper_doi               10.1021/acscatal.9b03019
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C24 H25 N2 O2'
_chemical_formula_sum            'C24 H25 N2 O2'
_chemical_formula_weight         373.48
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                105.617(5)
_cell_angle_beta                 100.765(5)
_cell_angle_gamma                93.916(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8691(5)
_cell_length_b                   10.1304(6)
_cell_length_c                   12.2386(8)
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2030
_cell_measurement_theta_min      2.1420
_cell_volume                     1032.17(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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   0.00 108.00  360
  2  \w    -69.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  176
  3  \w    -77.50  17.00   0.50    8.00    --  -20.00 -72.00 108.00  189
  4  \w    -41.00   0.00   0.50    8.00    --  -20.00  72.00  36.00   82
  5  \w    -54.00 -24.00   0.50    8.00    --  -20.00 -72.00-180.00   60
  6  \w    -31.00  -1.00   0.50    8.00    --  -20.00 -72.00 -36.00   60
  7  \w   -110.00 -20.00   0.50    8.00    --  -20.00   0.00-108.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0675292000
_diffrn_orient_matrix_UB_12      -0.0335895000
_diffrn_orient_matrix_UB_13      0.0044655000
_diffrn_orient_matrix_UB_21      0.0229955000
_diffrn_orient_matrix_UB_22      0.0265878000
_diffrn_orient_matrix_UB_23      -0.0431991000
_diffrn_orient_matrix_UB_31      0.0405434000
_diffrn_orient_matrix_UB_32      0.0594523000
_diffrn_orient_matrix_UB_33      0.0436833000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.768
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69557
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0820P)^2^+0.2680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2474
_reflns_number_total             3640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03019_si_002.cif
_cod_data_source_block           dm-sai2-pa-172-pa-25_mo
_cod_depositor_comments
;

2020-10-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.5(C24 H25 N2 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               4514617
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
;
_shelx_res_checksum              48213
_shelx_hkl_checksum              225
_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 2.567
_oxdiff_exptl_absorpt_empirical_full_min 0.670