Nickel-Catalyzed Decarbonylation of Aromatic Aldehydes.
Ding, Keying; Xu, Shi; Alotaibi, Rajeh; Paudel, Keshav; Reinheimer, Eric W.; Weatherly, Jessie; The Journal of organic chemistry 82 (2017) 4924–4929; doi:10.1021/acs.joc.7b00284

data_4032540
_publ_section_title
;
 Nickel-Catalyzed Decarbonylation of Aromatic Aldehydes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4924
_journal_page_last               4929
_journal_paper_doi               10.1021/acs.joc.7b00284
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C41 H70 Ni O2 P2'
_chemical_formula_sum            'C41 H70 Ni O2 P2'
_chemical_formula_weight         715.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-26
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                84.863(4)
_cell_angle_beta                 88.794(5)
_cell_angle_gamma                65.035(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7004(6)
_cell_length_b                   10.2894(5)
_cell_length_c                   21.5422(11)
_cell_measurement_reflns_used    11413
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.0760
_cell_measurement_theta_min      3.5950
_cell_volume                     1941.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Pilatus P200K HPC detector'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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    -93.00  59.00   0.50    3.00    --   -4.00  29.00  30.00  304
  2  \w    -75.00  30.00   0.50    3.00    --    9.20  55.00 150.00  210
  3  \w     57.00  83.00   0.50    3.00    --    9.20  55.00 150.00   52
  4  \w    -74.00  28.00   0.50    3.00    --    9.20  55.00 -90.00  204
  5  \w    -55.00  46.00   0.50    3.00    --    9.20  43.00 120.00  202
  6  \w     66.00  98.00   0.50    3.00    --    9.20  43.00 120.00   64
  7  \w    -74.00  18.00   0.50    3.00    --    9.20  55.00  30.00  184
  8  \w    -75.00 -52.50   0.50    3.00    --    9.20  29.00 -90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319240000
_diffrn_orient_matrix_UB_12      -0.0601624000
_diffrn_orient_matrix_UB_13      -0.0178689000
_diffrn_orient_matrix_UB_21      -0.0082132000
_diffrn_orient_matrix_UB_22      0.0468276000
_diffrn_orient_matrix_UB_23      -0.0272962000
_diffrn_orient_matrix_UB_31      0.0736287000
_diffrn_orient_matrix_UB_32      -0.0039872000
_diffrn_orient_matrix_UB_33      0.0053747000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13165
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.437
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.302
_refine_diff_density_max         1.559
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6872
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1361P)^2^+0.8257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1847
_refine_ls_wR_factor_ref         0.1926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5495
_reflns_number_total             6872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00284_si_002.cif
_cod_data_source_block           er_proc4_twin1_hklf4
_cod_database_code               4032540
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         'Ni P C H O'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5643(13) 0.4357(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 C3A-C4A \\sim C3B-C4B
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C3A \\sim C4B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C5B \\sim C2: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C3B \\sim O2B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C3B) = Uanis(C5A)
Uanis(C3B) = Uanis(C5B)
Uanis(C9) = Uanis(C3B)
5. Rigid body (RIGU) restrains
 C5A, C4A, C3A, O2A, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(O2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=1-FVAR(1)
 Sof(O2A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C6(H6), C36(H36), C24(H24), C18(H18), C12(H12), C30(H30)
7.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C31(H31A,H31B), C17(H17A,H17B), C37(H37A,H37B), C11(H11A,
 H11B), C28(H28A,H28B), C38(H38A,H38B), C7(H7A,H7B), C25(H25A,H25B), C41(H41A,
 H41B), C16(H16A,H16B), C29(H29A,H29B), C19(H19A,H19B), C32(H32A,H32B),
 C34(H34A,H34B), C13(H13A,H13B), C23(H23A,H23B), C14(H14A,H14B), C20(H20A,H20B),
  C26(H26A,H26B), C35(H35A,H35B), C10(H10A,H10B), C15(H15A,H15B), C22(H22A,
 H22B), C21(H21A,H21B), C40(H40A,H40B), C9(H9A,H9B), C27(H27A,H27B), C33(H33A,
 H33B), C8(H8A,H8B)
7.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C4A(H4A), C3A(H3A), C3B(H3B), C4B(H4B), C5B(H5B)
;
_shelx_res_checksum              82891
_shelx_hkl_checksum              29663
_shelx_shelxl_version_number     2014/7
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.747
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by 3.2260\% 
 around [0.63 -0.60 -0.49] (reciprocal) or [0.75 -0.67 -0.05] (direct)
;