N-Cyanomethylmethanimine tethered anthracene dimer: concise synthesis, conformational properties and photoinduced configurational isomerization
Younes, Eyad A.; Aljaar, Nayyef; Abdollahi, Maryam F.; Shtaiwi, Majed; Issa, Maram J.; Zhao, Yuming; New Journal of Chemistry 47 (2023) 6708–6720; doi:10.1039/D2NJ06320D

data_7062356
_publ_section_title
;
 N-Cyanomethylmethanimine tethered anthracene dimer: concise synthesis,
 conformational properties and photoinduced configurational isomerization
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6708
_journal_page_last               6720
_journal_paper_doi               10.1039/D2NJ06320D
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H20 N2'
_chemical_formula_sum            'C31 H20 N2'
_chemical_formula_weight         420.49
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2021-12-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-03 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                67.824(2)
_cell_angle_beta                 85.664(2)
_cell_angle_gamma                78.436(2)
_cell_formula_units_Z            1
_cell_length_a                   5.18100(10)
_cell_length_b                   9.6048(2)
_cell_length_c                   11.9887(3)
_cell_measurement_reflns_used    10439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1480
_cell_measurement_theta_min      3.9840
_cell_volume                     541.24(2)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_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 0.980
_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   -120.00 -33.00   0.50    5.00    --  -48.54 -63.00  95.00  174
  2  \w     33.00 121.00   0.50    5.00    --   48.54  63.00-127.00  176
  3  \w    -23.00  65.00   0.50    5.00    --   48.54 -63.00  95.00  176
  4  \w    -68.00 -18.00   0.50   15.00    --  -90.00  63.00-127.00  100
  5  \w   -161.00 -74.00   0.50   15.00    --  -90.00 -63.00  95.00  174
  6  \w     96.00 178.00   0.50   15.00    --  111.50  63.00-127.00  164
  7  \w     40.00  82.00   0.50   15.00    --  111.50 -63.00  95.00   84
  8  \w    -64.00  24.00   0.50    5.00    --  -48.54  63.00-127.00  176
  9  \w     34.00  95.00   0.50    5.00    --   48.54-125.00 -30.00  122
 10  \w    -25.00  30.00   0.50    5.00    --   48.54 -19.00   0.00  110
 11  \w    -25.00  30.00   0.50    5.00    --   48.54 -19.00  90.00  110
 12  \w   -161.00 -83.00   0.50   15.00    --  -90.00 -94.00   0.00  156
 13  \w    -65.00 -18.00   0.50   15.00    --  -90.00  61.00  60.00   94
 14  \w    -65.00 -18.00   0.50   15.00    --  -90.00  61.00  30.00   94
 15  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00  30.00  130
 16  \w     40.00  79.00   0.50   15.00    --  111.50 -61.00 150.00   78
 17  \w     95.00 178.00   0.50   15.00    --  111.50 125.00  60.00  166
 18  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00 120.00  130
 19  \w     40.00 111.00   0.50   15.00    --  111.50-125.00-150.00  142
 20  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00   0.00  130
 21  \w     40.00 106.00   0.50   15.00    --  111.50 -93.00-148.71  132
 22  \w    101.00 178.00   0.50   15.00    --  111.50  15.00  30.00  154
 23  \w     40.00  79.00   0.50   15.00    --  111.50 -61.00  30.00   78
 24  \w     40.00 111.00   0.50   15.00    --  111.50-125.00 -60.00  142
 25  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00  60.00  130
 26  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00  90.00  130
 27  \w     40.00  79.00   0.50   15.00    --  111.50 -61.00-150.00   78
 28  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00 -60.00  130
 29  \w    101.00 178.00   0.50   15.00    --  111.50  45.00 -60.00  154
 30  \w    101.00 178.00   0.50   15.00    --  111.50  45.00 150.00  154
 31  \w    101.00 178.00   0.50   15.00    --  111.50  45.00  60.00  154
 32  \w     40.00 111.00   0.50   15.00    --  111.50-125.00 -90.00  142
 33  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00 -30.00  130
 34  \w     40.00 105.00   0.50   15.00    --  111.50 -94.00 150.00  130
 35  \w     40.00  79.00   0.50   15.00    --  111.50 -61.00-120.00   78
 36  \w   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00 -90.00  186
 37  \w   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00-180.00  186
 38  \w   -120.00 -35.00   0.50    5.00    --  -48.54 -57.00-150.00  170
 39  \w   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00  30.00  186
 40  \w     27.00 121.00   0.50    5.00    --   48.54  77.00 -30.00  188
 41  \w     35.00 121.00   0.50    5.00    --   48.54  57.00 -60.00  172
 42  \w     27.00 121.00   0.50    5.00    --   48.54  77.00  30.00  188
 43  \w     27.00 121.00   0.50    5.00    --   48.54  77.00 120.00  188
 44  \w   -161.00 -83.00   0.50   15.00    --  -90.00 -77.00-150.00  156
 45  \w   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00 -60.00  186
 46  \w   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00  30.00  186
 47  \w   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00 163.06  186
 48  \w    101.00 178.00   0.50   15.00    --  111.50  30.00-150.00  154
 49  \w     31.00  57.00   0.50    5.00    --   48.54  77.00-180.00   52
 50  \w    -47.00 -22.00   0.50    5.00    --    2.00 130.00-141.19   50
 51  \w    -64.00 -39.00   0.50    5.00    --   10.00 167.00  -4.67   50
 52  \w     -4.00  21.00   0.50    5.00    --   26.00  95.00-146.78   50
 53  \w      4.00  29.00   0.50    5.00    --   34.00  95.00 -18.65   50
 54  \w     13.00  38.00   0.50    5.00    --   42.00  92.00  14.42   50
 55  \w     17.00  42.00   0.50    5.00    --   42.00  85.00  98.60   50
 56  \w    -60.00 -35.00   0.50    5.00    --  -48.54 -57.00 120.00   50
 57  \w    -52.00 -27.00   0.50    5.00    --  -48.54 -77.00-150.00   50
 58  \w   -114.00 -88.00   0.50    5.00    --  -48.54 -77.00-150.00   52
 59  \w     55.00  84.00   0.50    5.00    --   48.54  37.00   0.00   58
 60  \w     53.00  81.00   0.50    5.00    --   48.54  19.00-180.00   56
 61  \w    -62.00 -36.00   0.50    5.00    --  -58.00 -77.00 -65.53   52
 62  \w    -70.00 -44.00   0.50    5.00    --  -58.00 -57.00   4.95   52
 63  \w    -68.00 -42.00   0.50    5.00    --  -62.00 -72.00-132.26   52
 64  \w    -76.00 -50.00   0.50    5.00    --  -66.00 -67.00 151.75   52
 65  \w    -75.00 -49.00   0.50    5.00    --  -66.00 -68.00 -30.50   52
 66  \w    -76.00 -50.00   0.50    5.00    --  -66.00 -66.00   3.07   52
 67  \w     49.00  74.00   0.50    5.00    --   70.00  75.00 134.75   50
 68  \w     49.00  75.00   0.50    5.00    --   70.00  75.00  95.70   52
 69  \w    -79.00 -53.00   0.50   15.00    --  -70.00 -68.00 -86.39   52
 70  \w    -78.00 -52.00   0.50   15.00    --  -70.00 -67.00-176.10   52
 71  \w    -82.00 -57.00   0.50   15.00    --  -74.00 -65.00 -52.62   50
 72  \w    -84.00 -58.00   0.50   15.00    --  -78.00 -75.00 -14.03   52
 73  \w    -83.00 -57.00   0.50   15.00    --  -78.00 -74.00 143.52   52
 74  \w    -87.00 -62.00   0.50   15.00    --  -82.00 -73.00 105.42   50
 75  \w    -91.00 -65.00   0.50   15.00    --  -82.00 -66.00-141.78   52
 76  \w    -88.00 -62.00   0.50   15.00    --  -82.00 -72.00  74.90   52
 77  \w    -86.00 -60.00   0.50   15.00    --  -82.00 -77.00-131.34   52
 78  \w    -91.00 -65.00   0.50   15.00    --  -82.00 -68.00  33.18   52
 79  \w    -97.00 -71.00   0.50   15.00    --  -86.00 -61.00  49.22   52
 80  \w    -96.00 -71.00   0.50   15.00    --  -90.00 -70.00-132.58   50
 81  \w    -96.00 -70.00   0.50   15.00    --  -90.00 -77.00  90.00   52
 82  \w    -96.00 -70.00   0.50   15.00    --  -90.00 -77.00 -90.00   52
 83  \w    -95.00 -70.00   0.50   15.00    --  -90.00 -76.00 -82.09   50
 84  \w    -93.00 -68.00   0.50   15.00    --  -90.00 -77.00-150.00   50
 85  \w   -156.00-130.00   0.50   15.00    --  -90.00 -76.00 -82.09   52
 86  \w    -95.00 -69.00   0.50   15.00    --  -90.00 -77.00 150.00   52
 87  \w   -161.00-126.00   0.50   15.00    --  -90.00 -70.00-132.58   70
 88  \w    -98.00 -73.00   0.50   15.00    --  -90.00 -64.00 170.97   50
 89  \w    -95.00 -69.00   0.50   15.00    --  -90.00 -75.00  43.04   52
 90  \w   -102.00 -77.00   0.50   15.00    --  -90.00 -61.00 120.00   50
 91  \w    -97.00 -71.00   0.50   15.00    --  -90.00 -75.00 -15.97   52
 92  \w    -93.00 -68.00   0.50   15.00    --  -90.00 -77.00 -30.00   50
 93  \w   -100.00 -74.00   0.50   15.00    --  -90.00 -64.00  -3.09   52
 94  \w     91.00 117.00   0.50   15.00    --  111.50  77.00 -60.00   52
 95  \w    112.00 143.00   0.50   15.00    --  111.50  77.00-180.00   62
 96  \w     97.00 129.00   0.50   15.00    --  111.50  61.00 150.00   64
 97  \w    128.00 154.00   0.50   15.00    --  111.50  15.00   0.00   52
 98  \w     49.00  75.00   0.50   15.00    --  111.50-125.00  90.00   52
 99  \w    134.00 161.00   0.50   15.00    --  111.50  77.00   0.00   54
100  \w     48.00  74.00   0.50   15.00    --  111.50-125.00 -30.00   52
101  \w     90.00 116.00   0.50   15.00    --  111.50  77.00   0.00   52
102  \w     90.00 117.00   0.50   15.00    --  111.50  77.00-120.00   54
103  \w    121.00 147.00   0.50   15.00    --  111.50  77.00-150.00   52
104  \w    139.00 167.00   0.50   15.00    --  111.50  61.00  90.00   56
105  \w     99.00 129.00   0.50   15.00    --  111.50  61.00  90.00   60
106  \w     91.00 117.00   0.50   15.00    --  111.50  77.00-150.00   52
107  \w     93.00 119.00   0.50   15.00    --  111.50  77.00  90.00   52
108  \w    101.00 127.00   0.50   15.00    --  111.50  61.00   0.00   52
109  \w    130.00 156.00   0.50   15.00    --  111.50  77.00 150.00   52
110  \w     40.00  65.00   0.50   15.00    --  111.50 -61.00-180.00   50
111  \w     46.00  72.00   0.50   15.00    --  111.50-125.00  30.00   52
112  \w     95.00 122.00   0.50   15.00    --  111.50  77.00 150.00   54
113  \w     91.00 117.00   0.50   15.00    --  111.50  77.00  60.00   52
114  \w     93.00 118.00   0.50   15.00    --  111.50  77.00  30.00   50
115  \w    132.00 170.00   0.50   15.00    --  111.50  77.00 -90.00   76
116  \w    102.00 128.00   0.50   15.00    --  111.50  45.00   0.00   52
117  \w     94.00 127.00   0.50   15.00    --  111.50  77.00 -90.00   66
118  \w     98.00 151.00   0.50   15.00    --  111.50  61.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2126753000
_diffrn_orient_matrix_UB_12      0.0533806000
_diffrn_orient_matrix_UB_13      -0.0980584000
_diffrn_orient_matrix_UB_21      -0.1024930000
_diffrn_orient_matrix_UB_22      0.1448534000
_diffrn_orient_matrix_UB_23      0.0286851000
_diffrn_orient_matrix_UB_31      0.1907452000
_diffrn_orient_matrix_UB_32      0.0851242000
_diffrn_orient_matrix_UB_33      -0.0939037000
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17194
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.280
_diffrn_reflns_theta_min         3.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78837
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0606P)^2^+0.0162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3764
_reflns_number_total             4253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj06320d4.cif
_cod_data_source_block           soh
_cod_depositor_comments
'Adding full bibliography for 7062355--7062356.cif.'
_cod_database_code               7062356
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H20 N2'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.937
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.1(8)
 -0.1(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30)
;
_shelx_res_checksum              13309
_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 5.113
_oxdiff_exptl_absorpt_empirical_full_min 0.485