Palladium-catalyzed methylene C(sp3)–H arylation of the adamantyl scaffold
Lao, Ye-Xing; Wu, Jia-Qiang; Chen, Yunyun; Zhang, Shang-Shi; Li, Qingjiang; Wang, Honggen; Organic Chemistry Frontiers 2 (2015) 1374–; doi:10.1039/C5QO00218D

data_1553173
_publ_section_title
;
 Palladium-catalyzed methylene C(sp3)--H arylation of the adamantyl
 scaffold
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1374
_journal_paper_doi               10.1039/C5QO00218D
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 Cl F7 N O'
_chemical_formula_sum            'C26 H23 Cl F7 N O'
_chemical_formula_weight         533.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.9969(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.89225(14)
_cell_length_b                   15.11065(14)
_cell_length_c                   24.8076(3)
_cell_measurement_reflns_used    8060
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6000
_cell_measurement_theta_min      3.6320
_cell_volume                     4727.22(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega   26.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.2034   77.0000  -90.0000 95

  2 omega   79.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   30.0000 88

  3 omega   84.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   90.0000 80

  4 omega   79.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   60.0000 96

  5 omega   66.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -30.0000 26

  6 omega   69.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000    0.0000 90

  7 omega    8.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2034   77.0000 -150.0000 27

  8 omega  -63.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.2034   77.0000   90.0000 70

  9 omega -126.00  -26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -95.0000   77.0000  120.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0446969000
_diffrn_orient_matrix_UB_12      0.0687757000
_diffrn_orient_matrix_UB_13      -0.0350099000
_diffrn_orient_matrix_UB_21      0.0214737000
_diffrn_orient_matrix_UB_22      0.0639070000
_diffrn_orient_matrix_UB_23      0.0494406000
_diffrn_orient_matrix_UB_31      0.1116633000
_diffrn_orient_matrix_UB_32      -0.0397641000
_diffrn_orient_matrix_UB_33      0.0189621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10465
_diffrn_reflns_theta_full        71.56
_diffrn_reflns_theta_max         71.56
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         6282
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.150
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+1.3158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                6078
_reflns_number_total             6282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00218d2.cif
_cod_data_source_block           lyx_2_141118
_cod_original_cell_volume        4727.22(8)
_cod_database_code               1553173
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C7(H7), C8(H8), C33(H33), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C39(H39A,H39B), C35(H35A,H35B), C42(H42A,
 H42B), C40(H40A,H40B), C11(H11A,H11B), C37(H37A,H37B), C16(H16A,H16B), C9(H9A,
 H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C28(H28), C32(H32), C30(H30), C4(H4), C3(H3),
 C31(H31), C2(H2A)
2.d Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'