Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment
Li, Weikang; Huang, Ming; Liu, Jiahao; Huang, Yong-Liang; Lan, Xiao-Bing; Ye, Zongren; Zhao, Cunyuan; Liu, Yan; Ke, Zhuofeng; ACS Catalysis 11 (2021) 10377–10382; doi:10.1021/acscatal.1c02956

data_4518991
_publ_section_title
;
 Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct
 N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational
 Design to Experiment
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10377
_journal_page_last               10382
_journal_paper_doi               10.1021/acscatal.1c02956
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C17 H20 Mo N4 O4'
_chemical_formula_sum            'C17 H20 Mo N4 O4'
_chemical_formula_weight         440.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.613(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8980(5)
_cell_length_b                   14.1645(8)
_cell_length_c                   17.4273(10)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      59.188
_cell_measurement_theta_min      4.465
_cell_volume                     1927.6(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19226
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.375
_diffrn_reflns_theta_min         3.514
_exptl_absorpt_coefficient_mu    3.863
_exptl_absorpt_correction_T_max  0.3090
_exptl_absorpt_correction_T_min  0.1785
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method ch2cl2/hexane
_refine_diff_density_max         0.948
_refine_diff_density_min         -1.140
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0673P)^2^+1.1840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             4226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02956_si_003.cif
_cod_data_source_block           b20091602a0060_0m
_cod_database_code               4518991
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7(0.046) H9(0.04) H8(0.046) H12(0.049) H17A(0.041) H17B(0.041)
 H14(0.048) H13(0.051) H15A(0.089) H15B(0.089) H15C(0.089) H11A(0.088)
 H11B(0.088) H11C(0.088) H10A(0.099) H10B(0.099) H10C(0.099) H16A(0.11)
 H16B(0.11) H16C(0.11)
 Fixed X: H7(0.6465) H9(0.2315) H8(0.8854) H12(0.9386) H17A(0.7737)
 H17B(0.9096) H14(0.2974) H13(0.7413) H15A(0.4536) H15B(0.2521) H15C(0.3621)
 H11A(0.2884) H11B(0.1543) H11C(0.3495) H10A(0.3886) H10B(0.1907) H10C(0.3348)
 H16A(0.4302) H16B(0.3132) H16C(0.5164)
 Fixed Y: H7(0.1179) H9(0.1495) H8(0.1762) H12(0.4289) H17A(0.2066)
 H17B(0.2524) H14(0.4635) H13(0.558) H15A(0.6303) H15B(0.6122) H15C(0.5526)
 H11A(0.248) H11B(0.1665) H11C(0.1576) H10A(0.0021) H10B(0.0053) H10C(-0.0054)
 H16A(0.4998) H16B(0.5872) H16C(0.5919)
 Fixed Z: H7(0.3684) H9(0.4435) H8(0.4651) H12(0.6239) H17A(0.6467)
 H17B(0.598) H14(0.6379) H13(0.6449) H15A(0.5885) H15B(0.5827) H15C(0.5297)
 H11A(0.3406) H11B(0.3106) H11C(0.297) H10A(0.3686) H10B(0.3788) H10C(0.4533)
 H16A(0.7636) H16B(0.7304) H16C(0.7328)
;
_shelx_res_checksum              37019
_shelx_hkl_checksum              81651
_olex2_submission_special_instructions 'No special instructions were received'