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_1569560
_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_formula_moiety         'C22 H22 O3'
_chemical_formula_sum            'C22 H22 O3'
_chemical_formula_weight         334.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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
;
2022-11-01 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                88.8970(10)
_cell_angle_beta                 89.8080(10)
_cell_angle_gamma                83.7420(10)
_cell_formula_units_Z            4
_cell_length_a                   5.70840(10)
_cell_length_b                   12.2516(2)
_cell_length_c                   25.4722(4)
_cell_measurement_reflns_used    20430
_cell_measurement_temperature    100.1(5)
_cell_measurement_theta_max      68.1010
_cell_measurement_theta_min      1.7760
_cell_volume                     1770.51(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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      100.1(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_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    -87.00 -12.00   0.50    0.20    --  -40.33 125.00  40.00  150
  2  \w   -108.00 -57.00   0.50    0.20    --  -40.33-147.00 157.00  102
  3  \w   -102.00 -24.00   0.50    0.20    --  -40.33 147.00-153.00  156
  4  \w     45.00 105.00   0.50    0.20    --   40.33-147.00 157.00  120
  5  \w     34.00  91.00   0.50    0.20    --   40.33-125.00 -37.00  114
  6  \w    -87.00 -15.00   0.50    1.00    --  -82.50 125.00  40.00  144
  7  \w   -151.00 -57.00   0.50    1.00    --  -82.50-147.00 157.00  188
  8  \w   -150.00 -73.00   0.50    1.00    --  -82.50-125.00 -37.00  154
  9  \w   -102.00 -24.00   0.50    1.00    --  -82.50 147.00-153.00  156
 10  \w     79.00 164.00   0.50    1.00    --   96.67 147.00-153.00  170
 11  \w     94.00 163.00   0.50    1.00    --   96.67 125.00  40.00  138
 12  \w     45.00 128.00   0.50    1.00    --   96.67-147.00 157.00  166
 13  \w     34.00 112.00   0.50    1.00    --   96.67-125.00 -37.00  156
 14  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00 -60.00  118
 15  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00-180.00  118
 16  \w    -43.00  26.00   0.50    0.20    --  -40.33  38.00 -90.00  138
 17  \w    -56.00  26.00   0.50    0.20    --  -40.33  50.00  60.00  164
 18  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00-120.00  118
 19  \w    -43.00  26.00   0.50    0.20    --  -40.33  38.00-150.00  138
 20  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00  60.00  118
 21  \w     21.00 107.00   0.50    0.20    --   40.33  50.00  90.00  172
 22  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00 -60.00  122
 23  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00-150.00  122
 24  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00   0.00  118
 25  \w     41.00  99.00   0.50    0.20    --   40.33-138.00-180.00  116
 26  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00-180.00   64
 27  \w    -47.00 -15.00   0.50    1.00    --  -82.50  42.00  30.00   64
 28  \w    -80.00  -9.00   0.50    1.00    --  -82.50  96.00-180.00  142
 29  \w    -56.00 -16.00   0.50    1.00    --  -82.50  50.00  90.00   80
 30  \w   -160.00 -36.00   0.50    1.00    --  -82.50  -8.00 150.00  248
 31  \w     22.00 106.00   0.50    1.00    --   96.67 -96.00 -30.00  168
 32  \w     83.00 164.00   0.50    1.00    --   96.67  33.00  90.00  162
 33  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00  30.00   78
 34  \w    105.00 170.00   0.50    1.00    --   96.67  96.00 -90.00  130
 35  \w     30.00 109.00   0.50    1.00    --   96.67-117.00 -30.00  158
 36  \w    105.00 170.00   0.50    1.00    --   96.67  96.00-180.00  130
 37  \w     83.00 164.00   0.50    1.00    --   96.67  33.00 -90.00  162
 38  \w     75.00 164.00   0.50    1.00    --   96.67  59.00 120.00  178
 39  \w     81.00 164.00   0.50    1.00    --   96.67 145.00   0.00  166
 40  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00 -60.00   78
 41  \w     70.00 165.00   0.50    1.00    --   96.67  77.00 -60.00  190
 42  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00 120.00   54
 43  \w     28.00 105.00   0.50    1.00    --   96.67 -77.00-150.00  154
 44  \w     99.00 164.00   0.50    1.00    --   96.67 117.00 150.00  130
 45  \w     81.00 164.00   0.50    1.00    --   96.67 145.00-120.00  166
 46  \w     44.00 127.00   0.50    1.00    --   96.67-145.00-120.00  166
 47  \w     73.00 165.00   0.50    1.00    --   96.67  68.00-150.00  184
 48  \w     44.00 127.00   0.50    1.00    --   96.67-145.00 -90.00  166
 49  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00  90.00   78
 50  \w     29.00  68.00   0.50    1.00    --   96.67 -59.00-120.00   78
 51  \w     28.00 105.00   0.50    1.00    --   96.67 -77.00 -30.00  154
 52  \w    105.00 170.00   0.50    1.00    --   96.67  96.00 150.00  130
 53  \w    105.00 170.00   0.50    1.00    --   96.67  96.00 -30.00  130
 54  \w     99.00 164.00   0.50    1.00    --   96.67 117.00 120.00  130
 55  \w     30.00  57.00   0.50    1.00    --   96.67 -50.00-180.00   54
 56  \w     29.00  83.00   0.50    1.00    --   96.67 -68.00 120.00  108
 57  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -60.00  192
 58  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 150.00  192
 59  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  90.00  192
 60  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-120.00  192
 61  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00   0.00  192
 62  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -90.00  192
 63  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00-180.00  182
 64  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  30.00  192
 65  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  60.00  192
 66  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 120.00  190
 67  \w     14.00 109.00   0.50    0.20    --   40.33  77.00-150.00  190
 68  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 -90.00  190
 69  \w     17.00 108.00   0.50    0.20    --   40.33  64.00   0.00  182
;
_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      0.0238211000
_diffrn_orient_matrix_UB_12      -0.0013165000
_diffrn_orient_matrix_UB_13      -0.0602524000
_diffrn_orient_matrix_UB_21      -0.0277225000
_diffrn_orient_matrix_UB_22      0.1265117000
_diffrn_orient_matrix_UB_23      -0.0017458000
_diffrn_orient_matrix_UB_31      0.2690237000
_diffrn_orient_matrix_UB_32      -0.0007597000
_diffrn_orient_matrix_UB_33      0.0050785000
_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  0.0647
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30578
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.199
_diffrn_reflns_theta_min         1.735
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0595P)^2^+0.7758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5712
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02440g2.cif
_cod_data_source_block           kkuka076_auto_1
_cod_depositor_comments
;
Adding full bibliography for 1569557--1569560.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H44 O6'
_cod_original_formula_weight         668.79
_cod_original_formula_moiety         '2(C22 H22 O3)'
_cod_original_formula_units_Z            2
_cod_database_code               1569560
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     '100 K'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.937
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C34(H34), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C29(H29), C30(H30), C3(H3), C11(H11), C10(H10), C25(H25), C8(H8),
 C7(H7), C26(H26), C32(H32), C6(H6), C38(H38), C16(H16), C42(H42), C40(H40),
 C20(H20), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C23(H23a,H23b,H23c), C43(H43a,H43b,H43c), C21(H21a,H21b,
 H21c), C35(H35a,H35b,H35c), C13(H13a,H13b,H13c), C44(H44a,H44b,H44c), C22(H22a,
 H22b,H22c)
;
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.597