Efficient and chemoselective hydrogenation of aldehydes catalyzed by a well-defined PN3 -pincer manganese (II) catalyst precursor: an application in furfural conversion
Huang, Kuo-Wei; Gholap, Sandeep S.; Al-Dakhil, Abdullah; Chakraborty, Priyanka; Li, Huaifeng; Dutta, Indranil; Das, Pradip; Chemical Communications  (2021) –; doi:10.1039/D1CC04808B

data_7129115
_publ_section_title
;
 Efficient and chemoselective hydrogenation of aldehydes catalyzed by a
 well-defined PN3 -pincer manganese (II) catalyst precursor: an
 application in furfural conversion
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04808B
_journal_year                    2021
_chemical_formula_moiety         'C18 H26 Br2 Mn N3 P, C3 H7 N O'
_chemical_formula_sum            'C21 H33 Br2 Mn N4 O P'
_chemical_formula_weight         603.24
_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     iterative
_audit_creation_date             2020-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                96.607(5)
_cell_angle_beta                 97.226(5)
_cell_angle_gamma                94.321(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8591(13)
_cell_length_b                   10.2949(15)
_cell_length_c                   14.571(2)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      2.56
_cell_measurement_theta_min      32.64
_cell_volume                     1304.2(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43224
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.936
_diffrn_reflns_theta_min         2.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.650
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.3545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1348 before and 0.0999 after correction.
The Ratio of minimum to maximum transmission is 0.4749.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       Block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.351
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         9718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0723P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6462
_reflns_number_total             9718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04808b2.cif
_cod_data_source_block           Cat2
_cod_database_code               7129115
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.559
_shelx_estimated_absorpt_t_min   0.501
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C1(H1), C7(H7), C8(H8), C2(H2), C19(H19), C3(H3A), C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C20(H20A,
 H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'