Construction of sterically bent π-conjugated arylene by implanting into bulky NHC Cu(i) coordination polymers in crystalline media
Tomita, Ryunosuke; Jin, Mingoo; CrystEngComm 27 (2025) 5618–5624; doi:10.1039/D5CE00346F

data_7250614
_publ_section_title
;
 Construction of sterically bent \p-conjugated arylene by implanting into
 bulky NHC Cu(i) coordination polymers in crystalline media
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              5618
_journal_page_last               5624
_journal_paper_doi               10.1039/D5CE00346F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C49 H48 Cu N4, B C24 F20'
_chemical_formula_sum            'C73 H48 B Cu F20 N4'
_chemical_formula_weight         1435.50
_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             2025-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-29 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                113.2060(10)
_cell_angle_beta                 90.6480(10)
_cell_angle_gamma                94.6670(10)
_cell_formula_units_Z            2
_cell_length_a                   11.41140(10)
_cell_length_b                   16.17480(10)
_cell_length_c                   19.6865(2)
_cell_measurement_reflns_used    84892
_cell_measurement_temperature    153
_cell_measurement_theta_max      76.1580
_cell_measurement_theta_min      2.9620
_cell_volume                     3324.89(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      153
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_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   -119.00 -39.00   0.50    0.05    --  -48.41 -44.00  71.00  160
  2  \w    -65.00 -40.00   0.50    0.05    --  -62.00 -79.00  46.75   50
  3  \w    -73.00 -48.00   0.50    0.05    --  -70.00 -80.00 100.06   50
  4  \w    -81.00 -55.00   0.50    0.05    --  -74.00 -72.00  45.02   52
  5  \w    -84.00 -59.00   0.50    0.05    --  -78.00 -72.00  70.55   50
  6  \w    -86.00 -59.00   0.50    0.05    --  -78.00 -74.00  97.26   54
  7  \w    -85.00 -59.00   0.50    0.05    --  -78.00 -75.00 149.60   52
  8  \w    -89.00 -64.00   0.50    0.05    --  -82.00 -71.00 121.12   50
  9  \w    -94.00 -68.00   0.50    0.05    --  -86.00 -71.00 178.26   52
 10  \w    -96.00 -71.00   0.50    0.05    --  -90.00 -72.00 131.39   50
 11  \w    -95.00 -66.00   0.50    0.05    --  -86.00 -74.00  82.42   58
 12  \w    -97.00 -70.00   0.50    0.05    --  -90.00 -74.00  69.16   54
 13  \w    -98.00 -62.00   0.50    0.05    --  -82.00 -74.00  39.62   72
 14  \w    -93.00 -68.00   0.50    0.05    --  -86.00 -71.00 -11.02   50
 15  \w    -89.00 -63.00   0.50    0.05    --  -78.00 -67.00 -49.21   52
 16  \w    -87.00 -62.00   0.50    0.05    --  -82.00 -75.00-104.46   50
 17  \w    -90.00 -63.00   0.50    0.05    --  -82.00 -73.00-153.34   54
 18  \w    -94.00 -68.00   0.50    0.05    --  -86.00 -73.00-125.18   52
 19  \w    -91.00 -65.00   0.50    0.05    --  -82.00 -67.00 -63.29   52
 20  \w    -95.00 -68.00   0.50    0.05    --  -86.00 -73.00-112.30   54
 21  \w   -107.00 -63.00   0.50    0.05    --  -82.00 -72.00 -83.00   88
 22  \w    -98.00 -73.00   0.50    0.05    --  -94.00 -77.00 -11.01   50
 23  \w    -98.00 -72.00   0.50    0.05    --  -94.00 -79.00  19.31   52
 24  \w   -116.00 -78.00   0.50    0.05    --  -94.00 -64.00  53.38   76
 25  \w   -130.00-104.00   0.50    0.05    --  -62.00 -79.00  46.75   52
 26  \w   -137.00-109.00   0.50    0.05    --  -86.00 -71.00 -11.02   56
 27  \w   -120.00 -77.00   0.50    0.05    --  -94.00 -67.00 -38.44   86
 28  \w   -134.00-100.00   0.50    0.05    --  -86.00 -73.00-125.18   68
 29  \w   -131.00 -71.00   0.50    0.05    --  -90.00 -73.00-154.31  120
 30  \w   -135.00 -72.00   0.50    0.05    --  -94.00 -79.00 -48.23  126
 31  \w   -137.00 -78.00   0.50    0.05    --  -98.00 -77.00 -55.71  118
 32  \w   -152.00-108.00   0.50    0.05    --  -86.00 -73.00-112.30   88
 33  \w   -151.00 -75.00   0.50    0.05    --  -94.00 -73.00-179.20  152
 34  \w   -156.00 -68.00   0.50    0.05    --  -86.00 -70.00 -93.26  176
 35  \w    -46.00  24.00   0.50    0.05    --  -48.41  44.00-137.00  140
 36  \w    -43.00 -17.00   0.50    0.05    --    6.00 131.00 -45.46   52
 37  \w      0.00  28.00   0.50    0.05    --   30.00  96.00 -50.29   56
 38  \w     15.00  42.00   0.50    0.05    --   42.00  90.00 -31.62   54
 39  \w     34.00 125.00   0.50    0.05    --   54.00  76.00  -2.17  182
 40  \w    104.00 130.00   0.50    0.05    --   70.00  77.00  -7.03   52
 41  \w    113.00 138.00   0.50    0.05    --   66.00  76.00  68.64   50
 42  \w     43.00  86.00   0.50    0.05    --   62.00  73.00 149.51   86
 43  \w     46.00  72.00   0.50    0.05    --   66.00  76.00  68.64   52
 44  \w     41.00  98.00   0.50    0.05    --   62.00  79.00  20.41  114
 45  \w     44.00  71.00   0.50    0.05    --   66.00  80.00 -58.49   54
 46  \w     40.00  66.00   0.50    0.05    --   62.00  80.00 -12.82   52
 47  \w     49.00  74.00   0.50    0.05    --   70.00  77.00  -7.03   50
 48  \w     48.00  77.00   0.50    0.05    --   70.00  80.00  26.84   58
 49  \w     36.00 129.00   0.50    0.05    --   58.00  80.00 107.26  186
 50  \w     37.00  62.00   0.50    0.05    --   58.00  77.00 144.67   50
 51  \w     44.00  78.00   0.50    0.05    --   66.00  80.00 152.79   68
 52  \w     28.00 121.00   0.50    0.05    --   50.00  80.00  95.22  186
 53  \w     40.00  66.00   0.50    0.05    --   62.00  80.00 -67.67   52
 54  \w     41.00  66.00   0.50    0.05    --   62.00  79.00-124.70   50
 55  \w     48.00  79.00   0.50    0.05    --   66.00  72.00-134.73   62
 56  \w     49.00  74.00   0.50    0.05    --   70.00  77.00-107.98   50
 57  \w     44.00  70.00   0.50    0.05    --   62.00  72.00-163.67   52
 58  \w     59.00  84.00   0.50    0.05    --   78.00  73.00-171.14   50
 59  \w     94.00 174.00   0.50    0.05    --  102.75  44.00-137.00  160
 60  \w     81.00 106.00   0.50    0.05    --  102.75 -99.00   0.00   50
 61  \w     80.00 106.00   0.50    0.05    --  102.75 -99.00 120.00   52
 62  \w     85.00 111.00   0.50    0.05    --  102.75-125.00 150.00   52
 63  \w     55.00  81.00   0.50    0.05    --  102.75-125.00 150.00   52
 64  \w     31.00 104.00   0.50    0.05    --  102.75 -99.00  60.00  146
 65  \w     33.00 106.00   0.50    0.05    --  102.75 -99.00 -90.00  146
 66  \w     32.00 102.00   0.50    0.05    --  102.75 -99.00-120.00  140
 67  \w     32.00 105.00   0.50    0.05    --  102.75 -99.00-180.00  146
 68  \w     31.00  87.00   0.50    0.05    --  102.75 -99.00-150.00  112
 69  \w     31.00  64.00   0.50    0.05    --  102.75 -99.00   0.00   66
 70  \w    -22.00  50.00   0.50    0.05    --   48.41 -44.00  71.00  144
 71  \w     12.00  42.00   0.50    0.05    --   38.00  89.00-107.22   60
 72  \w     28.00 119.00   0.50    0.05    --   48.41  77.00-120.00  182
 73  \w     40.00 119.00   0.50    0.05    --   48.41  44.00-137.00  158
 74  \w     32.00 125.00   0.50    0.05    --   54.00  80.00 -85.96  186
 75  \w     32.00 125.00   0.50    0.05    --   54.00  80.00-126.43  186
 76  \w     11.00  42.00   0.50    0.05    --   38.00  90.00  84.62   62
 77  \w     16.00  42.00   0.50    0.05    --   42.00  88.00  29.52   52
 78  \w    -14.00  21.00   0.50    0.05    --   18.00 100.00  73.17   70
 79  \w     15.00  41.00   0.50    0.05    --   42.00  91.00 157.21   52
 80  \w    -39.00 -13.00   0.50    0.05    --    6.00 124.00 166.36   52
 81  \w    -94.00 -14.00   0.50    0.05    --  -48.41 125.00   0.00  160
 82  \w    -61.00  24.00   0.50    0.05    --  -48.41  57.00 -60.00  170
 83  \w     -3.00  30.00   0.50    0.05    --   26.00  95.00-150.71   66
 84  \w    -96.00 -30.00   0.50    0.05    -- -102.00 125.00 -30.00  132
 85  \w    -60.00 -34.00   0.50    0.05    -- -102.00  57.00 -60.00   52
 86  \w    -83.00 -30.00   0.50    0.05    -- -102.00 125.00 -90.00  106
 87  \w   -108.00 -69.00   0.50    0.05    -- -102.00 125.00 -60.00   78
 88  \w    -94.00 -30.00   0.50    0.05    -- -102.00 125.00  90.00  128
 89  \w    -62.00 -30.00   0.50    0.05    -- -102.00  57.00 120.00   64
 90  \w    -55.00 -30.00   0.50    0.05    -- -102.00  57.00  90.00   50
 91  \w   -151.00 -70.00   0.50    0.05    --  -90.00 -76.00  29.62  162
 92  \w   -152.00 -79.00   0.50    0.05    --  -94.00 -63.00 159.07  146
 93  \w   -158.00 -66.00   0.50    0.05    --  -86.00 -74.00 101.28  184
 94  \w   -161.00 -71.00   0.50    0.05    --  -90.00 -72.00 150.23  180
 95  \w   -159.00-126.00   0.50    0.05    --  -94.00 -79.00  19.31   66
 96  \w   -155.00 -82.00   0.50    0.05    --  -98.00 -66.00  43.95  146
 97  \w   -164.00-138.00   0.50    0.05    --  -94.00 -79.00 -48.23   52
 98  \w   -166.00 -73.00   0.50    0.05    --  -94.00 -78.00 -76.08  186
 99  \w   -165.00 -77.00   0.50    0.05    --  -94.00 -68.00-136.84  176
100  \w   -158.00-120.00   0.50    0.05    --  -94.00 -64.00  53.38   76
101  \w   -155.00 -78.00   0.50    0.05    --  -98.00 -77.00  96.08  154
102  \w   -168.00 -77.00   0.50    0.05    --  -98.00 -78.00 -13.18  182
103  \w   -165.00 -76.00   0.50    0.05    --  -98.00 -79.00 136.78  178
104  \w   -174.00 -93.00   0.50    0.05    -- -102.00 -44.00  71.00  162
;
_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      0.1118376000
_diffrn_orient_matrix_UB_12      0.0116808000
_diffrn_orient_matrix_UB_13      -0.0396526000
_diffrn_orient_matrix_UB_21      0.0588781000
_diffrn_orient_matrix_UB_22      -0.0661491000
_diffrn_orient_matrix_UB_23      0.0252902000
_diffrn_orient_matrix_UB_31      -0.0491338000
_diffrn_orient_matrix_UB_32      -0.0795065000
_diffrn_orient_matrix_UB_33      -0.0710901000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            123929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.271
_diffrn_reflns_theta_min         2.445
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00106(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         13389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+1.9576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12315
_reflns_number_total             13389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00346f2.cif
_cod_data_source_block           NHC-Cu(I)-coordination-polymer-1
_cod_depositor_comments
'Adding full bibliography for 7250614--7250616.cif.'
_cod_original_cell_volume        3324.88(5)
_cod_database_code               7250614
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N B F Cu'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.875
_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:
 C80(H80), C71(H71), C68(H68), C83(H83)
2.b Aromatic/amide H refined with riding coordinates:
 C98(H98), C97(H97), C91(H91), C94(H94), C66(H66), C95(H95), C56(H56),
 C50(H50), C78(H78), C65(H65), C77(H77), C90(H90), C76(H76), C87(H87), C54(H54),
  C64(H64), C88(H88), C55(H55), C52(H52), C51(H51)
2.c Idealised Me refined as rotating group:
 C82(H82A,H82B,H82C), C81(H81A,H81B,H81C), C73(H73A,H73B,H73C), C85(H85A,H85B,
 H85C), C72(H72A,H72B,H72C), C84(H84A,H84B,H84C), C70(H70A,H70B,H70C), C69(H69A,
 H69B,H69C)
;
_shelx_res_checksum              73272
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.796