Asymmetric alkene-alkene reductive cross-coupling reaction via visible-light photoredox/cobalt dual catalysis
Maiti, Mamata; Jana, Sayan Kumar; Maji, Biplab; Chemical Communications  (2023) –; doi:10.1039/D3CC02792A

data_7131893
_publ_section_title
;
 Asymmetric alkene-alkene reductive cross-coupling reaction via
 visible-light photoredox/cobalt dual catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02792A
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H25 N O3'
_chemical_formula_sum            'C19 H25 N O3'
_chemical_formula_weight         315.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-06-09 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.13080(10)
_cell_length_b                   11.62940(10)
_cell_length_c                   25.4879(3)
_cell_measurement_reflns_used    15675
_cell_measurement_temperature    100.3(9)
_cell_measurement_theta_max      67.9410
_cell_measurement_theta_min      3.4620
_cell_volume                     1817.22(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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      100.3(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -108.00 -23.00   0.50    0.30    --  -40.58 -44.00-137.00  170
  2  \w    -78.00   4.00   0.50    0.30    --  -40.58 104.00-126.00  164
  3  \w    -50.00  27.00   0.50    0.30    --  -40.58  44.00  12.00  154
  4  \w    -22.00  70.00   0.50    0.30    --   40.58 -83.00  23.00  184
  5  \w    -25.00  50.00   0.50    0.30    --   40.58 -44.00-137.00  150
  6  \w     18.00  78.00   0.50    0.30    --   40.58-104.00 132.00  120
  7  \w     23.00 108.00   0.50    0.30    --   40.58  44.00  12.00  170
  8  \w   -153.00 -83.00   0.50    1.90    --  -82.50-104.00 132.00  140
  9  \w   -152.00 -78.00   0.50    1.90    --  -82.50 -83.00  23.00  148
 10  \w   -150.00 -65.00   0.50    1.90    --  -82.50 -44.00-137.00  170
 11  \w    -82.00 -12.00   0.50    1.90    --  -82.50 104.00-126.00  140
 12  \w     26.00 108.00   0.50    1.90    --   96.35-104.00 132.00  164
 13  \w     27.00 125.00   0.50    1.90    --   96.35 -83.00  23.00  196
 14  \w    105.00 167.00   0.50    1.90    --   96.35 104.00-126.00  124
 15  \w     79.00 164.00   0.50    1.90    --   96.35  44.00  12.00  170
 16  \w   -108.00 -17.00   0.50    0.30    --  -40.58 -64.00  60.00  182
 17  \w    -69.00  29.00   0.50    0.30    --  -40.58  83.00 143.00  196
 18  \w   -111.00 -13.00   0.50    1.90    --  -82.50  83.00 143.00  196
 19  \w    -47.00 -15.00   0.50    1.90    --  -82.50  42.00 -90.00   64
 20  \w     29.00  83.00   0.50    1.90    --   96.35 -68.00 -60.00  108
 21  \w     28.00  68.00   0.50    1.90    --   96.35 -59.00-120.00   80
 22  \w     30.00  57.00   0.50    1.90    --   96.35 -50.00 150.00   54
 23  \w    105.00 170.00   0.50    1.90    --   96.35  96.00-150.00  130
 24  \w     30.00  57.00   0.50    1.90    --   96.35 -50.00 120.00   54
 25  \w     83.00 164.00   0.50    1.90    --   96.35  33.00 -90.00  162
 26  \w     30.00  57.00   0.50    1.90    --   96.35 -50.00   0.00   54
 27  \w     28.00  68.00   0.50    1.90    --   96.35 -59.00  90.00   80
 28  \w     30.00  57.00   0.50    1.90    --   96.35 -50.00-180.00   54
 29  \w   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 -60.00  190
 30  \w   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00   0.00  190
 31  \w   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00-150.00  190
 32  \w   -108.00 -17.00   0.50    0.30    --  -40.58 -64.00 150.00  182
 33  \w   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00  90.00  190
 34  \w   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 150.00  190
 35  \w    -29.00  31.00   0.50    0.30    --   40.58 -25.00   0.00  120
 36  \w     14.00 109.00   0.50    0.30    --   40.58  77.00  90.00  190
 37  \w     70.00 165.00   0.50    1.90    --   96.35  77.00-180.00  190
 38  \w     33.00 110.00   0.50    1.90    --   96.35-117.00 -30.00  154
 39  \w     75.00 165.00   0.50    1.90    --   96.35  59.00 -60.00  180
 40  \w     72.00 164.00   0.50    1.90    --   96.35  68.00 150.00  184
 41  \w     77.00 163.00   0.50    1.90    --   96.35  50.00  60.00  172
 42  \w     72.00 164.00   0.50    1.90    --   96.35  68.00 -30.00  184
 43  \w     77.00 163.00   0.50    1.90    --   96.35  50.00 120.00  172
 44  \w     29.00  76.00   0.50    1.90    --   96.35 -68.00 150.00   94
 45  \w     75.00 165.00   0.50    1.90    --   96.35  59.00  90.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0647245000
_diffrn_orient_matrix_UB_12      -0.1274238000
_diffrn_orient_matrix_UB_13      0.0056287000
_diffrn_orient_matrix_UB_21      -0.1235593000
_diffrn_orient_matrix_UB_22      -0.0063205000
_diffrn_orient_matrix_UB_23      0.0525550000
_diffrn_orient_matrix_UB_31      -0.2089881000
_diffrn_orient_matrix_UB_32      -0.0357344000
_diffrn_orient_matrix_UB_33      -0.0293118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.990
_diffrn_reflns_theta_min         3.468
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0429P)^2^+1.0458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3197
_reflns_number_total             3309
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02792a2.cif
_cod_data_source_block           msm_mb_237r_auto
_cod_database_code               7131893
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.747
_reflns_odcompleteness_completeness 100.00
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C16) = Uanis(C18) = Uanis(C19)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              32740
_shelx_hkl_checksum              46720
_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.354