Catalytic Synthesis of a Methylmalonate Salt from Ethylene and Carbon Dioxide through Photoinduced Activation and Photoredox-Catalyzed Reduction of Nickelalactones
Takahashi, Kohei; Sakurazawa, Yuji; Iwai, Asaki; Iwasawa, Nobuharu; ACS Catalysis 12 (2022) 3776–3781; doi:10.1021/acscatal.2c01053

data_4519383
_publ_section_title
;
 Catalytic Synthesis of a Methylmalonate Salt from Ethylene and Carbon
 Dioxide through Photoinduced Activation and Photoredox-Catalyzed
 Reduction of Nickelalactones
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              3776
_journal_page_last               3781
_journal_paper_doi               10.1021/acscatal.2c01053
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C29 H41 N2 Ni O4 P, C4 H9 N O'
_chemical_formula_sum            'C33 H50 N3 Ni O5 P'
_chemical_formula_weight         658.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.271(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5365(9)
_cell_length_b                   15.9821(6)
_cell_length_c                   12.9995(6)
_cell_measurement_reflns_used    7103
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.1380
_cell_measurement_theta_min      3.8560
_cell_volume                     3408.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -18.00  23.00   0.50   18.39    --   46.86 -40.00  21.00   82
  2  \w     35.00  69.00   0.50   73.57    --  104.75 -61.00 -30.00   68
  3  \w     75.00 102.00   0.50   73.57    --  104.75 -94.00-120.00   54
  4  \w     34.00  68.00   0.50   73.57    --  104.75 -94.00-120.00   68
  5  \w    146.00 174.00   0.50   73.57    --  104.75  30.00 -90.00   56
  6  \w     92.00 133.00   0.50   73.57    --  104.75  30.00 -90.00   82
  7  \w     76.00 114.00   0.50   18.39    --   46.86  40.00 175.00   76
  8  \w    108.00 134.00   0.50   73.57    --  104.75  40.00 175.00   52
  9  \w    -24.00  23.00   0.50   18.39    --  -46.86  19.00 -30.00   94
 10  \w    -57.00 -31.00   0.50   73.57    -- -102.00  61.00  90.00   52
 11  \w    -61.00 -34.00   0.50   73.57    -- -102.00  61.00 120.00   54
 12  \w    -63.00 -38.00   0.50   73.57    -- -102.00  61.00 150.00   50
 13  \w    -29.00  26.00   0.50   18.39    --  -46.86  40.00 175.00  110
 14  \w   -115.00 -46.00   0.50   18.39    --  -46.86 -40.00  21.00  138
 15  \w   -112.00 -84.00   0.50   18.39    --  -46.86-125.00  90.00   56
 16  \w   -159.00-101.00   0.50   73.57    -- -102.00 -94.00 120.00  116
 17  \w   -166.00 -86.00   0.50   73.57    -- -102.00 -40.00  21.00  160
 18  \w    -69.00 -29.00   0.50   73.57    -- -102.00  61.00   0.00   80
 19  \w    -64.00 -37.00   0.50   73.57    -- -102.00  61.00  30.00   54
 20  \w    -69.00 -41.00   0.50   73.57    -- -102.00  61.00 -30.00   56
 21  \w    -67.00 -42.00   0.50   73.57    -- -102.00  61.00 -90.00   50
 22  \w    -69.00 -30.00   0.50   73.57    -- -102.00  61.00 -60.00   78
 23  \w    -69.00 -30.00   0.50   73.57    -- -102.00  61.00-180.00   78
 24  \w   -113.00 -81.00   0.50   18.39    --  -46.86-125.00-180.00   64
 25  \w   -167.00 -93.00   0.50   73.57    -- -102.00 -30.00 -60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0868416000
_diffrn_orient_matrix_UB_12      -0.0065985000
_diffrn_orient_matrix_UB_13      -0.0584694000
_diffrn_orient_matrix_UB_21      0.0277751000
_diffrn_orient_matrix_UB_22      0.0476577000
_diffrn_orient_matrix_UB_23      -0.0924348000
_diffrn_orient_matrix_UB_31      0.0226269000
_diffrn_orient_matrix_UB_32      -0.0834962000
_diffrn_orient_matrix_UB_33      -0.0480380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0913P)^2^+1.3346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4467
_reflns_number_total             6223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs2c01053_si_002.cif
_cod_data_source_block           191128ai-706
_cod_database_code               4519383
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         NiO4PN2C31H43
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Ternary CH refined with riding coordinates:
 C15(H15), C21(H21), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C13(H13A,H13B), C20(H20A,H20B), C26(H26A,H26B), C19(H19A,
 H19B), C18(H18A,H18B), C22(H22A,H22B), C17(H17A,H17B), C24(H24A,H24B),
 C25(H25A,H25B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C36(H36A,H36B,
 H36C), C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              7667
_shelx_hkl_checksum              44317
_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 2.308
_oxdiff_exptl_absorpt_empirical_full_min 0.490