Solvent-less Dehydrogenative C–H Etherification with Alcohols Using Mechanochemistry
Zhou, Kun; Hao, Hong-Yan; Mao, Yang-Jie; Wu, Qiu-Zi; Chen, Lei; Wang, Shuang; Jin, Wu; Xu, Zhen-Yuan; Lou, Shao-Jie; Xu, Dan-Qian; ACS Sustainable Chemistry & Engineering 9 (2021) 4433–4439; doi:10.1021/acssuschemeng.0c08201

data_4518547
_publ_section_title
;
 Solvent-less Dehydrogenative C--H Etherification with Alcohols Using
 Mechanochemistry
;
_journal_issue                   12
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              4433
_journal_page_last               4439
_journal_paper_doi               10.1021/acssuschemeng.0c08201
_journal_volume                  9
_journal_year                    2021
_chemical_formula_moiety         'C20 H27 N O2'
_chemical_formula_sum            'C20 H27 N O2'
_chemical_formula_weight         313.42
_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             2019-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                68.787(5)
_cell_angle_beta                 73.015(4)
_cell_angle_gamma                71.871(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9105(8)
_cell_length_b                   10.1433(14)
_cell_length_c                   12.1778(13)
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.930
_cell_measurement_theta_min      8.28
_cell_volume                     847.74(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      169.96
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9780
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.948
_diffrn_reflns_theta_min         4.564
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1013 before and 0.0707 after correction. The Ratio of minimum to maximum transmission is 0.7948. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0616P)^2^+0.2147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2798
_reflns_number_total             3202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc0c08201_si_002.cif
_cod_data_source_block           1907151008_0m
_cod_depositor_comments          'Adding full bibliography for 4518547.cif.'
_cod_original_cell_volume        847.74(18)
_cod_database_code               4518547
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.954
_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:
 C13(H13), C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,
 H17B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              26506
_shelx_hkl_checksum              31167
_olex2_submission_special_instructions 'No special instructions were received'