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_4518990
_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         'C13 H12 Mo N4 O4'
_chemical_formula_sum            'C13 H12 Mo N4 O4'
_chemical_formula_weight         384.21
_chemical_name_systematic        Mo-1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3874(2)
_cell_length_b                   8.85320(10)
_cell_length_c                   25.1701(3)
_cell_measurement_reflns_used    4208
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7970
_cell_measurement_theta_min      4.7810
_cell_volume                     2983.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -112.00 -35.00   1.00    3.09    --  -41.14 -38.00  90.00   77
  2  \w    -82.00 -46.00   1.00    3.09    --  -41.14 125.00-180.00   36
  3  \w     -2.00  34.00   1.00    3.09    --   41.14 -19.00 150.00   36
  4  \w     82.00 178.00   1.00   14.00    --  107.79  61.00  60.00   96
  5  \w    107.00 132.00   1.00   14.00    --  107.79 -45.00 -90.00   25
  6  \w     35.00  61.00   1.00   14.00    --  107.79 -45.00 -90.00   26
  7  \w     38.00 117.00   1.00   14.00    --  107.79-125.00-120.00   79
  8  \w    109.00 152.00   1.00   14.00    --  107.79 125.00 -90.00   43
  9  \w     47.00  88.00   1.00   14.00    --  107.79 -94.00   0.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7513
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.955
_diffrn_reflns_theta_min         3.512
_exptl_absorpt_coefficient_mu    7.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0568P)^2^+0.0159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             2958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02956_si_002.cif
_cod_data_source_block           2038859
_cod_database_code               4518990
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7(0.034) H9(0.032) H10(0.035) H13A(0.028) H13B(0.028)
 H12A(0.049) H12B(0.049) H12C(0.049) H8(0.041) H11A(0.081) H11B(0.081)
 H11C(0.081)
 Fixed X: H7(0.5249) H9(0.679) H10(0.6472) H13A(0.6679) H13B(0.6877)
 H12A(0.6217) H12B(0.5833) H12C(0.5101) H8(0.3643) H11A(0.2926) H11B(0.2747)
 H11C(0.346)
 Fixed Y: H7(0.1879) H9(0.3218) H10(0.5105) H13A(0.3197) H13B(0.4796)
 H12A(0.8699) H12B(0.7728) H12C(0.8162) H8(0.2694) H11A(0.625) H11B(0.5107)
 H11C(0.6493)
 Fixed Z: H7(0.3367) H9(0.4846) H10(0.5539) H13A(0.3834) H13B(0.3585)
 H12A(0.5102) H12B(0.5581) H12C(0.5119) H8(0.2992) H11A(0.3331) H11B(0.2864)
 H11C(0.2783)
;
_shelx_res_checksum              52853
_shelx_hkl_checksum              73567
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;