Copper catalyzed benzylic sp<sup>3</sup> C-H alkenylation.
Chen, Ting-An; Staples, Richard J.; Warren, Timothy H.; Chemical science 15 (2024) 17685–17690; doi:10.1039/d4sc03430a

data_1572623
_publ_section_title
;
 Copper catalyzed benzylic sp<sup>3</sup> C-H alkenylation.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              17685
_journal_page_last               17690
_journal_paper_doi               10.1039/d4sc03430a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C24 H26 B Cl4 Cu N2 O2'
_chemical_formula_sum            'C24 H26 B Cl4 Cu N2 O2'
_chemical_formula_weight         590.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-26 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81870(10)
_cell_length_b                   13.46770(10)
_cell_length_c                   20.27360(10)
_cell_measurement_reflns_used    30230
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.8350
_cell_measurement_theta_min      3.9540
_cell_volume                     2608.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -39.00  28.00   0.50    0.05    --  -47.10  19.00 150.00  134
  2  \w    -70.00  16.00   0.50    0.05    --  -47.10  77.00  90.00  172
  3  \w    -47.00  26.00   0.50    0.05    --  -47.10  37.00   0.00  146
  4  \w    -47.00  26.00   0.50    0.05    --  -47.10  37.00-120.00  146
  5  \w     35.00 120.00   0.50    0.05    --   47.10  37.00-180.00  170
  6  \w     35.00 119.00   0.50    0.05    --   47.10  45.00-103.64  168
  7  \w     35.00 119.00   0.50    0.05    --   47.10  45.00  29.78  168
  8  \w     35.00 120.00   0.50    0.05    --   47.10  37.00  90.00  170
  9  \w     34.00 119.00   0.50    0.05    --   47.10  47.00 122.69  170
 10  \w     35.00 119.00   0.50    0.05    --   47.10  45.00 -16.37  168
 11  \w    110.00 178.00   0.50    0.20    --  113.25  77.00-180.00  136
 12  \w    101.00 178.00   0.50    0.20    --  113.25  45.00-180.00  154
 13  \w    106.00 178.00   0.50    0.20    --  113.25  61.00-150.00  144
 14  \w    101.00 178.00   0.50    0.20    --  113.25  45.00-120.00  154
 15  \w    101.00 178.00   0.50    0.20    --  113.25  45.00 -90.00  154
 16  \w    101.00 178.00   0.50    0.20    --  113.25  30.00 -30.00  154
 17  \w    101.00 178.00   0.50    0.20    --  113.25  30.00  30.00  154
 18  \w    101.00 178.00   0.50    0.20    --  113.25  45.00  90.00  154
 19  \w    101.00 178.00   0.50    0.20    --  113.25  30.00 120.00  154
 20  \w    100.00 178.00   0.50    0.20    --  113.25  15.00-180.00  156
 21  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00-180.00  124
 22  \w     36.00  93.00   0.50    0.05    --   47.10-125.00-180.00  114
 23  \w     44.00 108.00   0.50    0.20    --  113.25-125.00-180.00  128
 24  \w     44.00 108.00   0.50    0.20    --  113.25-125.00 -30.00  128
 25  \w     44.00 108.00   0.50    0.20    --  113.25-125.00  30.00  128
 26  \w     44.00 108.00   0.50    0.20    --  113.25-125.00   0.00  128
 27  \w     43.00 105.00   0.50    0.20    --  113.25-105.00 -18.24  124
 28  \w     44.00 108.00   0.50    0.20    --  113.25-125.00  60.00  128
 29  \w     43.00 104.00   0.50    0.20    --  113.25 -96.00 141.83  122
 30  \w     44.00 108.00   0.50    0.20    --  113.25-125.00 150.00  128
 31  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00 150.00  124
 32  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00  90.00  124
 33  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00  30.00  124
 34  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00  60.00  124
 35  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00 -90.00  124
 36  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00-120.00  124
 37  \w     42.00 104.00   0.50    0.20    --  113.25 -94.00-150.00  124
 38  \w     42.00  94.00   0.50    0.20    --  113.25 -77.00-120.00  104
 39  \w     42.00  94.00   0.50    0.20    --  113.25 -77.00-180.00  104
 40  \w     42.00  94.00   0.50    0.20    --  113.25 -77.00  30.00  104
 41  \w     42.00  94.00   0.50    0.20    --  113.25 -77.00  60.00  104
 42  \w     42.00  69.00   0.50    0.20    --  113.25 -61.00  90.00   54
 43  \w     42.00  94.00   0.50    0.20    --  113.25 -77.00 150.00  104
 44  \w     42.00  69.00   0.50    0.20    --  113.25 -61.00   0.00   54
 45  \w     42.00  69.00   0.50    0.20    --  113.25 -61.00 -60.00   54
 46  \w    -70.00 -19.00   0.50    0.20    --  -91.75  61.00 -90.00  102
 47  \w    -70.00 -19.00   0.50    0.20    --  -91.75  61.00   0.00  102
 48  \w    -70.00 -19.00   0.50    0.20    --  -91.75  61.00  60.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1274593000
_diffrn_orient_matrix_UB_12      0.0577369000
_diffrn_orient_matrix_UB_13      -0.0121024000
_diffrn_orient_matrix_UB_21      0.0465136000
_diffrn_orient_matrix_UB_22      -0.0922363000
_diffrn_orient_matrix_UB_23      -0.0340604000
_diffrn_orient_matrix_UB_31      -0.0871943000
_diffrn_orient_matrix_UB_32      0.0352274000
_diffrn_orient_matrix_UB_33      -0.0692354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            53838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.380
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.153
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.504
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1208
_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0387P)^2^+1.9234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5318
_reflns_number_total             5673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03430a2.cif
_cod_data_source_block           tc_14_cl2nncu_prenylbester
_cod_depositor_comments
'Adding full bibliography for 1572623--1572624.cif.'
_cod_database_code               1572623
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C24H26BCl4CuN2O2
_chemical_oxdiff_usercomment     PhF/C5
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.384
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              57312
_shelx_hkl_checksum              15425
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TC-14-(Cl2NNCu)-PrenylBester
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.774