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_4514616
_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         'C23 N3 O Pd'
_chemical_formula_sum            'C23 N3 O Pd'
_chemical_formula_weight         440.65
_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'
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                105.639(2)
_cell_angle_beta                 103.125(2)
_cell_angle_gamma                104.695(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6348(3)
_cell_length_b                   10.7198(3)
_cell_length_c                   11.5837(3)
_cell_measurement_reflns_used    8947
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.2560
_cell_measurement_theta_min      2.2880
_cell_volume                     1056.88(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -99.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  236
  3  \w   -106.50  19.00   0.50    8.00    --  -20.00 -72.00  36.00  251
  4  \w    -41.50 -33.50   0.50    8.00    --  -20.00  72.00-180.00   16
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0496934000
_diffrn_orient_matrix_UB_12      0.0305551000
_diffrn_orient_matrix_UB_13      0.0237634000
_diffrn_orient_matrix_UB_21      -0.0503803000
_diffrn_orient_matrix_UB_22      -0.0222889000
_diffrn_orient_matrix_UB_23      -0.0623395000
_diffrn_orient_matrix_UB_31      -0.0378530000
_diffrn_orient_matrix_UB_32      -0.0623756000
_diffrn_orient_matrix_UB_33      0.0066829000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8831
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.925
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.136
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+2.4003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3443
_reflns_number_total             3701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03019_si_004.cif
_cod_data_source_block           dm-aj-53_mo_sq
_cod_depositor_comments
;

2020-09-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         176.26
_cod_original_formula_moiety         '0.4(C23 N3 O Pd)'
_cod_original_formula_units_Z            5
_cod_original_cell_volume        1056.87(6)
_cod_original_formula_sum        'C9.20 N1.20 O0.40 Pd0.40'
_cod_database_code               4514616
_reflns_odcompleteness_completeness 87.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.03
_olex2_refinement_description
;
;
_shelx_res_checksum              41998
_shelx_hkl_checksum              5943
_shelx_fab_checksum              80426
_shelx_shelxl_version_number     2014/7
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.837