Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms
Appiagyei, Benjamin; Bhatia, Souful; Keeney, Gabriela L.; Dolmetsch, Troy; Jackson, James E.; Green Chemistry 22 (2020) 860–869; doi:10.1039/C9GC03747K

data_7239730
_publ_section_title
;
 Electroactivated alkylation of amines with alcohols via both direct and
 indirect borrowing hydrogen mechanisms
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              860
_journal_page_last               869
_journal_paper_doi               10.1039/C9GC03747K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 N3 O7, C11 H22 N'
_chemical_formula_sum            'C17 H24 N4 O7'
_chemical_formula_weight         396.40
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2254dt
_audit_creation_date             2019-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-22 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.825(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1396(18)
_cell_length_b                   15.021(4)
_cell_length_c                   17.652(5)
_cell_measurement_reflns_used    5842
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.32
_cell_volume                     1879.7(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.425
_diffrn_reflns_theta_min         1.786
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0887 before and 0.0674 after correction. The Ratio of minimum to maximum transmission is 0.7084. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0637
_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^)+(0.1020P)^2^+1.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.2027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2169
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03747k2.cif
_cod_data_source_block           nej419a
_cod_depositor_comments
;Adding full bibliography for 7239730.cif.

 Adding full bibliography for 7239730.cif.
;
_cod_original_cell_volume        1879.6(8)
_cod_database_code               7239730
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.955
_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. Restrained distances
 O6-N4 \\sim O6B-N4 \\sim O7-N4 \\sim O7B-N4
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(O7B) = Uanis(O7)
Uanis(O6B) = Uanis(O6)
Uanis(O7) = Uanis(O6B)
Uanis(O7B) = Uanis(O6)
4. Others
 Sof(O6B)=Sof(O7B)=1-FVAR(1)
 Sof(O6)=Sof(O7)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              75102
_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 'BBA 1001B'
_olex2_submission_special_instructions 'No special instructions were received'