NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant
Yao, Wei-Wei; Li, Ran; Li, Jiang-Fei; Sun, Juan; Ye, Mengchun; Green Chemistry 21 (2019) 2240–; doi:10.1039/C9GC00653B

data_1550815
_publ_section_title
;
 NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines
 using isopropanol as a reductant
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2240
_journal_paper_doi               10.1039/C9GC00653B
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H30 N2 O2 S'
_chemical_formula_sum            'C30 H30 N2 O2 S'
_chemical_formula_weight         482.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-26 deposited with the CCDC.    2019-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.72050(10)
_cell_length_b                   19.9636(3)
_cell_length_c                   21.5679(3)
_cell_measurement_reflns_used    6671
_cell_measurement_temperature    120.3(8)
_cell_measurement_theta_max      74.1400
_cell_measurement_theta_min      3.0500
_cell_volume                     2463.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.3(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -42.00  59.00   0.25    0.20    --   39.45 -26.00   4.00  404
  2  \w    -65.00 -28.00   0.25    0.80    -- -100.00  98.00 -27.00  148
  3  \w     33.00  93.00   0.25    0.80    --  109.49-125.00 148.00  240
  4  \w     66.00 164.00   0.25    0.80    --  109.49  26.00 167.00  392
  5  \w    -96.00 -24.00   0.25    0.20    --  -39.45 125.00-133.00  288
  6  \w     81.00 110.00   0.25    0.20    --   39.45  57.00 -30.00  116
  7  \w   -129.00 -23.00   0.25    0.80    -- -100.00  45.00   0.00  424
  8  \w     37.00  63.00   0.25    0.80    --  109.49 -77.00 -30.00  104
  9  \w     54.00 106.00   0.25    0.80    --  109.49-125.00  60.00  208
 10  \w     32.00  62.00   0.25    0.80    --  109.49-125.00   0.00  120
 11  \w     55.00 107.00   0.25    0.80    --  109.49 -94.00 150.00  208
 12  \w     77.00 103.00   0.25    0.80    --  109.49-125.00   0.00  104
 13  \w     99.00 141.00   0.25    0.80    --  109.49 -77.00 -30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0069680000
_diffrn_orient_matrix_UB_12      0.0114315000
_diffrn_orient_matrix_UB_13      -0.0706184000
_diffrn_orient_matrix_UB_21      0.0914290000
_diffrn_orient_matrix_UB_22      -0.0718853000
_diffrn_orient_matrix_UB_23      -0.0093448000
_diffrn_orient_matrix_UB_31      -0.2531650000
_diffrn_orient_matrix_UB_32      -0.0256469000
_diffrn_orient_matrix_UB_33      -0.0053540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9500
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.028
_diffrn_reflns_theta_max         67.028
_diffrn_reflns_theta_min         3.016
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.403
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0883P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4129
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00653b2.cif
_cod_data_source_block           ye_02_01
_cod_depositor_comments          'Adding full bibliography for 1550815.cif.'
_cod_database_code               1550815
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H30 N1 O2 S1'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.705
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=
 Sof(N3)=1-FVAR(1)
 Sof(N2)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(H32C)=FVAR(1)
4.a Riding coordinates:
 N1(H1)
4.b Ternary CH refined with riding coordinates:
 C5(H5)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
4.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              93050
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 5.169
_oxdiff_exptl_absorpt_empirical_full_min 0.394