A π-conjugated covalent organic framework enables interlocked nickel/photoredox catalysis for light-harvesting cross-coupling reactions.
Jati, Ayan; Dam, Suranjana; Kumar, Shekhar; Kumar, Kundan; Maji, Biplab; Chemical science 14 (2023) 8624–8634; doi:10.1039/d3sc02440g

data_1569557
_publ_section_title
;
 A &#x3c0;-conjugated covalent organic framework enables interlocked
 nickel/photoredox catalysis for light-harvesting cross-coupling
 reactions.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              8624
_journal_page_last               8634
_journal_paper_doi               10.1039/d3sc02440g
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H30 O S'
_chemical_formula_sum            'C19 H30 O S'
_chemical_formula_weight         306.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-10-29 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.306(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   44.2057(9)
_cell_length_b                   7.38100(10)
_cell_length_c                   5.60640(10)
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    298.5(7)
_cell_measurement_theta_max      67.8820
_cell_measurement_theta_min      6.0060
_cell_volume                     1827.79(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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_environment      air
_diffrn_ambient_temperature      298.5(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_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    -31.00  11.00   0.50    1.71    --  -41.21  25.00 -30.00   84
  2  \w    -27.00  29.00   0.50    1.71    --  -41.21  25.00 -90.00  112
  3  \w    -14.00  32.00   0.50    1.71    --  -41.21  12.00-120.00   92
  4  \w     -6.00  28.00   0.50    1.71    --  -41.21  25.00-180.00   68
  5  \w    -14.00  21.00   0.50    1.71    --  -41.21  25.00-150.00   70
  6  \w    -35.00  15.00   0.50    1.71    --  -41.21  38.00-120.00  100
  7  \w    -44.00 -16.00   0.50    9.00    --  -82.50  42.00 -30.00   56
  8  \w    -57.00 -27.00   0.50    9.00    --  -82.50  50.00 -90.00   60
  9  \w    -85.00  -9.00   0.50    1.71    --  -41.21 121.00-107.00  152
 10  \w    -84.00 -15.00   0.50    9.00    --  -82.50 121.00-107.00  138
 11  \w    -51.00 -18.00   0.50    9.00    --  -82.50  50.00  60.00   66
 12  \w    -30.00  28.00   0.50    1.71    --  -41.21  25.00 150.00  116
 13  \w    -49.00 -18.00   0.50    1.71    --  -41.21 -64.00   0.00   62
 14  \w     49.00 111.00   0.50    1.71    --   41.21-155.00  11.00  124
 15  \w     96.00 127.00   0.50    9.00    --   96.67-145.00  30.00   62
 16  \w     67.00  98.00   0.50    9.00    --   96.67-117.00  60.00   62
 17  \w     63.00 109.00   0.50    9.00    --   96.67-117.00   0.00   92
 18  \w     94.00 127.00   0.50    9.00    --   96.67-145.00 -90.00   66
 19  \w     82.00 108.00   0.50    9.00    --   96.67-145.00-120.00   52
 20  \w     69.00 127.00   0.50    9.00    --   96.67-145.00-180.00  116
 21  \w     42.00  67.00   0.50    9.00    --   96.67 -59.00 -90.00   50
 22  \w     33.00  73.00   0.50    9.00    --   96.67 -77.00-120.00   80
 23  \w     33.00 106.00   0.50    9.00    --   96.67 -96.00-180.00  146
 24  \w     34.00 104.00   0.50    9.00    --   96.67 -77.00-150.00  140
 25  \w     34.00  66.00   0.50    9.00    --   96.67-117.00 -30.00   64
 26  \w     49.00 133.00   0.50    9.00    --   96.67-155.00  11.00  168
 27  \w     61.00 109.00   0.50    9.00    --   96.67-145.00 120.00   96
 28  \w     78.00 127.00   0.50    9.00    --   96.67-145.00 150.00   98
 29  \w     38.00  65.00   0.50    9.00    --   96.67 -59.00  60.00   54
 30  \w     31.00  64.00   0.50    9.00    --   96.67 -59.00   0.00   66
 31  \w     34.00  67.00   0.50    9.00    --   96.67 -59.00 -30.00   66
 32  \w     29.00  92.00   0.50    9.00    --   96.67 -77.00 -30.00  126
 33  \w     30.00  57.00   0.50    9.00    --   96.67 -50.00-120.00   54
 34  \w     30.00  72.00   0.50    9.00    --   96.67 -68.00-180.00   84
 35  \w     74.00 156.00   0.50    9.00    --   96.67  17.00 -60.00  164
 36  \w    140.00 166.00   0.50    9.00    --   96.67  25.00   0.00   52
 37  \w    109.00 169.00   0.50    9.00    --   96.67  96.00 -60.00  120
 38  \w    111.00 143.00   0.50    9.00    --   96.67 117.00-120.00   64
 39  \w    106.00 131.00   0.50    9.00    --   96.67 121.00-107.00   50
 40  \w    105.00 164.00   0.50    9.00    --   96.67 117.00 -90.00  118
 41  \w    104.00 165.00   0.50    9.00    --   96.67  68.00  30.00  122
 42  \w     83.00 110.00   0.50    9.00    --   96.67  25.00   0.00   54
 43  \w     78.00 146.00   0.50    9.00    --   96.67  50.00  60.00  136
 44  \w     73.00 164.00   0.50    9.00    --   96.67  77.00   0.00  182
 45  \w     81.00 125.00   0.50    9.00    --   96.67 145.00-150.00   88
 46  \w     70.00 165.00   0.50    9.00    --   96.67  77.00 -30.00  190
 47  \w     74.00 135.00   0.50    9.00    --   96.67 155.00  50.00  122
 48  \w     72.00 108.00   0.50    1.71    --   41.21  50.00  90.00   72
 49  \w     26.00  61.00   0.50    1.71    --   41.21  50.00  90.00   70
 50  \w      9.00  35.00   0.50    1.71    --   41.21  93.00 -24.65   52
 51  \w      8.00  34.00   0.50    1.71    --   41.21  94.00 -62.55   52
 52  \w     11.00  36.00   0.50    1.71    --   41.21  88.00 -90.77   50
 53  \w     15.00  42.00   0.50    1.71    --   41.21  83.00-109.11   54
 54  \w     12.00  37.00   0.50    1.71    --   41.21  85.00-136.13   50
 55  \w    -21.00  42.00   0.50    1.71    --   41.21 -38.00 -30.00  126
 56  \w     19.00  71.00   0.50    1.71    --   41.21-104.00  30.00  104
 57  \w     34.00  61.00   0.50    9.00    --   96.67-117.00 120.00   54
 58  \w     31.00 111.00   0.50    9.00    --   96.67-121.00 169.00  160
 59  \w     31.00  89.00   0.50    1.71    --   41.21-121.00 169.00  116
 60  \w   -110.00 -52.00   0.50    1.71    --  -41.21-155.00  11.00  116
 61  \w   -107.00 -27.00   0.50    1.71    --  -41.21 155.00  50.00  160
 62  \w   -107.00 -27.00   0.50    9.00    --  -82.50 155.00  50.00  160
 63  \w   -108.00 -34.00   0.50    1.71    --  -41.21 -50.00 120.00  148
 64  \w   -109.00 -54.00   0.50    1.71    --  -41.21 -64.00   0.00  110
 65  \w   -132.00 -60.00   0.50    9.00    --  -82.50 -76.00-108.51  144
 66  \w   -146.00 -52.00   0.50    9.00    --  -82.50-155.00  11.00  188
 67  \w   -149.00 -75.00   0.50    9.00    --  -82.50-121.00 169.00  148
 68  \w   -150.00 -89.00   0.50    9.00    --  -82.50 -96.00 -60.00  122
 69  \w   -143.00 -78.00   0.50    9.00    --  -82.50 -87.00-180.00  130
;
_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      0.0294687000
_diffrn_orient_matrix_UB_12      -0.1075040000
_diffrn_orient_matrix_UB_13      -0.0306316000
_diffrn_orient_matrix_UB_21      0.0180984000
_diffrn_orient_matrix_UB_22      0.1783881000
_diffrn_orient_matrix_UB_23      0.0019872000
_diffrn_orient_matrix_UB_31      0.0045745000
_diffrn_orient_matrix_UB_32      -0.0133410000
_diffrn_orient_matrix_UB_33      0.2732619000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10076
_diffrn_reflns_point_group_measured_fraction_full 0.742
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.053
_diffrn_reflns_theta_min         2.000
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.114
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.078(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0668P)^2^+0.2590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.505
_reflns_Friedel_fraction_full    0.502
_reflns_Friedel_fraction_max     0.496
_reflns_number_gt                2406
_reflns_number_total             2467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02440g2.cif
_cod_data_source_block           sek117_1
_cod_depositor_comments
'Adding full bibliography for 1569557--1569560.cif.'
_cod_database_code               1569557
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O'
_chemical_oxdiff_usercomment     298K
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.94
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C8(H8a,H8b), C6(H6a,H6b), C5(H5a,H5b), C11(H11a,H11b), C4(H4a,
 H4b), C7(H7a,H7b), C9(H9a,H9b), C3(H3a,H3b), C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C1(H1a,H1b,H1c)
;
_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 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.596