Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons
Dey, Aniruddha; Sasmal, Sheuli; Seth, Kapileswar; Lahiri, Goutam Kumar; Maiti, Debabrata; ACS Catalysis  (2016) 433–; doi:10.1021/acscatal.6b03040

data_4513993
_publ_section_title
;
 Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic
 Hydrocarbons
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              433
_journal_paper_doi               10.1021/acscatal.6b03040
_journal_year                    2016
_chemical_formula_moiety         'C30 H30 Ni O2 P2'
_chemical_formula_sum            'C30 H30 Ni O2 P2'
_chemical_formula_weight         543.19
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4310(16)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.9022(3)
_cell_length_b                   9.9937(2)
_cell_length_c                   43.3265(7)
_cell_measurement_reflns_used    17877
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0090
_cell_measurement_theta_min      2.1430
_cell_volume                     8181.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.998
_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   -110.00  44.00   0.50    8.00    --  -20.00   0.00 108.00  308
  2  \w    -64.00   7.00   0.50    8.00    --  -20.00 -72.00  36.00  142
  3  \w    -30.00   0.00   0.50    8.00    --  -20.00   0.00-180.00   60
  4  \w   -110.00  40.00   0.50    8.00    --  -20.00   0.00  36.00  300
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224769000
_diffrn_orient_matrix_UB_12      -0.0231873000
_diffrn_orient_matrix_UB_13      0.0117261000
_diffrn_orient_matrix_UB_21      -0.0288495000
_diffrn_orient_matrix_UB_22      -0.0015996000
_diffrn_orient_matrix_UB_23      -0.0107835000
_diffrn_orient_matrix_UB_31      0.0084504000
_diffrn_orient_matrix_UB_32      -0.0670718000
_diffrn_orient_matrix_UB_33      -0.0037856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            30608
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.881
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.724
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+1.0430P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6244
_reflns_number_total             7198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b03040_si_002.cif
_cod_data_source_block           dm-snn-l2-56-1_mo
_cod_original_cell_volume        8182.0(3)
_cod_database_code               4513993
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C90 Ni3 O6 P6'
_reflns_odcompleteness_completeness 89.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.14
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00c,H00d), C00G(H00e,H00f), C00U(H00n,H00u)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00F(H00k), C00I(H00I), C00K(H00l),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C013(H013), C014(H014), C015(H015), C016(H016), C017(H017),
 C01A(H01i), C01B(H01d), C01C(H01e), C01F(H01j), C01G(H01k), C01H(H01l)
2.c Idealised Me refined as rotating group:
 C00L(H00g,H00h,H00j), C012(H01a,H01b,H01c), C019(H01f,H01g,H01h)
;
_shelx_res_checksum              12912
_shelx_hkl_checksum              33708
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.802