Sustainable electrochemical dehydrogenative C(sp3)–H mono/di-alkylations
He, Jin-Yu; Qian, Wei-Feng; Wang, Yan-Zhao; Yao, Chaochao; Wang, Nana; Liu, Huilin; Zhong, Bing; Zhu, Cuiju; Xu, Hao; Green Chemistry 24 (2022) 2483–2491; doi:10.1039/D1GC04479F

data_7244483
_publ_section_title
;
 Sustainable electrochemical dehydrogenative C(sp3)--H mono/di-alkylations
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2483
_journal_page_last               2491
_journal_paper_doi               10.1039/D1GC04479F
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H31 N O3'
_chemical_formula_sum            'C30 H31 N O3'
_chemical_formula_weight         453.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-09-29
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_audit_update_record
;
2021-10-27 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.224(4)
_cell_length_b                   14.043(7)
_cell_length_c                   21.164(10)
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.63
_cell_measurement_theta_min      3.29
_cell_volume                     2444(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10751
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        52.499
_diffrn_reflns_theta_max         52.499
_diffrn_reflns_theta_min         3.286
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
; 
 Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_extinction_coef       0.0026(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0694
_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^)+(0.0933P)^2^+1.3131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2963
_reflns_number_total             4142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04479f3.cif
_cod_data_source_block           210924n_0m
_cod_depositor_comments
'Adding full bibliography for 7244482--7244484.cif.'
_cod_database_code               7244483
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.961
_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, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B), C20(H20A,H20B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), 
 C22(H22), C26(H26) 
2.c Idealised Me refined as rotating group: 
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), 
 C30(H30A,H30B,H30C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O1(H1), O2(H2A) 
;
_shelx_res_checksum              66177
_olex2_submission_special_instructions 'No special instructions were received'