Temperature-modulated selective C(sp3)−H or C(sp2)−H arylation through palladium catalysis
Gogula, Thirupathi; Zhang, Jinquan; Reddy, Madhava; Zhang, Shuaizhong; Zou, Hongbin; Chemical Science  (2020) –; doi:10.1039/D0SC02328K

data_1559192
_publ_section_title
;
 Temperature-modulated selective C(sp3)&#x2212;H or C(sp2)&#x2212;H
 arylation through palladium catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02328K
_journal_year                    2020
_chemical_formula_moiety         'C23 H24 N4 O'
_chemical_formula_sum            'C23 H24 N4 O'
_chemical_formula_weight         372.46
_chemical_name_common            SP24OMe
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-02 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                81.6620(10)
_cell_angle_beta                 82.0120(10)
_cell_angle_gamma                79.0930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4235(3)
_cell_length_b                   9.4517(3)
_cell_length_c                   11.8728(4)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.97
_cell_volume                     1020.62(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         2.644
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.9231.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0566P)^2^+0.2254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4042
_reflns_number_total             4492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02328k2.cif
_cod_data_source_block           191105_t191104_0m
_cod_database_code               1559192
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C22 \\sim C20-C22A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 C20-C23 \\sim C20-C23A
 with sigma of 0.02
3. Rigid bond restraints
 C20, C21, C22, C23, C21A, C22A, C23A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C21A \\sim C22A \\sim C23A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Others
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17)
6.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F)
;
_shelx_res_checksum              4545
_olex2_submission_special_instructions 'No special instructions were received'