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_7062355
_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_formula_moiety         'C23 H15 Br N2'
_chemical_formula_sum            'C23 H15 Br N2'
_chemical_formula_weight         399.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-09-14 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   45.2994(6)
_cell_length_b                   6.08550(10)
_cell_length_c                   12.8728(2)
_cell_measurement_reflns_used    11250
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7620
_cell_measurement_theta_min      3.8870
_cell_volume                     3544.60(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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      N~2~
_diffrn_ambient_temperature      100(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 0.983
_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   -119.00 -25.00   0.50    1.23    --  -47.08 -74.00 120.00  188
  2  \w    -69.00  26.00   0.50    1.23    --  -47.08  74.00-110.00  190
  3  \w    -25.00  70.00   0.50    1.23    --   47.08 -74.00 120.00  190
  4  \w     25.00 120.00   0.50    1.23    --   47.08  74.00-110.00  190
  5  \w    -92.00 -19.00   0.50    4.92    --  -91.75  74.00-110.00  146
  6  \w   -164.00 -69.00   0.50    4.92    --  -91.75 -74.00 120.00  190
  7  \w     91.00 178.00   0.50    4.92    --  113.25  74.00-110.00  174
  8  \w     41.00 106.00   0.50    4.92    --  113.25 -74.00 120.00  130
  9  \w   -119.00 -73.00   0.50    1.23    --  -47.08-125.00-150.00   92
 10  \w   -119.00 -73.00   0.50    1.23    --  -47.08-125.00 -60.00   92
 11  \w    -16.00  28.00   0.50    1.23    --  -47.08  19.00  60.00   88
 12  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00 -30.00   76
 13  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00-180.00   76
 14  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00   0.00   76
 15  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00 120.00   76
 16  \w     99.00 178.00   0.50    4.92    --  113.25  30.00-150.00  158
 17  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00-150.00   76
 18  \w     96.00 178.00   0.50    4.92    --  113.25  15.00 -30.00  164
 19  \w     41.00 106.00   0.50    4.92    --  113.25 -94.00-180.00  130
 20  \w     96.00 178.00   0.50    4.92    --  113.25  61.00   0.00  164
 21  \w     99.00 178.00   0.50    4.92    --  113.25  30.00 -30.00  158
 22  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00  30.00   76
 23  \w     41.00 111.00   0.50    4.92    --  113.25-125.00 -90.00  140
 24  \w     96.00 178.00   0.50    4.92    --  113.25  15.00-180.00  164
 25  \w     99.00 178.00   0.50    4.92    --  113.25  30.00  30.00  158
 26  \w     41.00  79.00   0.50    4.92    --  113.25 -61.00 -90.00   76
 27  \w   -119.00 -23.00   0.50    1.23    --  -47.08 -77.00 -30.00  192
 28  \w   -121.00 -32.00   0.50    1.23    --  -47.08 -37.00 150.00  178
 29  \w   -119.00 -56.00   0.50    1.23    --  -47.08 -77.00  60.00  126
 30  \w   -119.00 -39.00   0.50    1.23    --  -47.08 -77.00  30.00  160
;
_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      -0.0124167000
_diffrn_orient_matrix_UB_12      -0.2067450000
_diffrn_orient_matrix_UB_13      0.0514808000
_diffrn_orient_matrix_UB_21      -0.0240757000
_diffrn_orient_matrix_UB_22      -0.0176419000
_diffrn_orient_matrix_UB_23      -0.0882484000
_diffrn_orient_matrix_UB_31      0.0206226000
_diffrn_orient_matrix_UB_32      -0.1449620000
_diffrn_orient_matrix_UB_33      -0.0626275000
_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  0.0485
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.559
_diffrn_reflns_theta_min         3.908
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.496
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+12.1074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj06320d4.cif
_cod_data_source_block           sw
_cod_depositor_comments
'Adding full bibliography for 7062355--7062356.cif.'
_cod_database_code               7062355
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H15BrN2
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.675
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Restrained distances
 H11-C11
 0.91 with sigma of 0.02
;
_shelx_res_checksum              81387
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.792