Studies of cyanomethylcarbamoyl-bridged anthracene and pyrene fluorophores
Younes, Eyad A.; Issa, Maram J.; Abdollahi, Maryam F.; Ding, Yuan-Fu; Rasras, Anas J.; Mok, Greta S. P.; Lin, Jian-Bin; Zhao, Yuming; New Journal of Chemistry 45 (2021) 17366–17376; doi:10.1039/D1NJ03044B

data_7060907
_publ_section_title
;
 Studies of cyanomethylcarbamoyl-bridged anthracene and pyrene
 fluorophores
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17366
_journal_page_last               17376
_journal_paper_doi               10.1039/D1NJ03044B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-09-20 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                110.229(2)
_cell_angle_beta                 96.599(2)
_cell_angle_gamma                106.447(2)
_cell_formula_units_Z            4
_cell_length_a                   9.8120(2)
_cell_length_b                   12.8630(3)
_cell_length_c                   15.4670(3)
_cell_measurement_reflns_used    18419
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9290
_cell_measurement_theta_min      3.1140
_cell_volume                     1706.93(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.83a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.83a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.83a (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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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 -35.00   0.50    0.44    --  -47.95 -47.00 -32.00  168
  2  \w    -16.00  28.00   0.50    0.44    --  -47.95  19.00  30.00   88
  3  \w    -46.00 -14.00   0.50    2.00    --  -86.25  47.00 115.00   64
  4  \w    -46.00  25.00   0.50    0.44    --  -47.95  47.00 115.00  142
  5  \w    -23.00  61.00   0.50    0.44    --   47.95 -47.00 -32.00  168
  6  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00-120.00   88
  7  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00-165.27  142
  8  \w     34.00  96.00   0.50    0.44    --   47.95-125.00-180.00  124
  9  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00 -60.00  142
 10  \w     35.00 112.00   0.50    2.00    --  107.75-125.00 -30.00  154
 11  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00   0.00  142
 12  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00  30.00   88
 13  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00  30.00  142
 14  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00 120.00   88
 15  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00 150.00  142
 16  \w     35.00 112.00   0.50    2.00    --  107.75-125.00   0.00  154
 17  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00-120.00  142
 18  \w     94.00 178.00   0.50    2.00    --  107.75  15.00-150.00  168
 19  \w     95.00 178.00   0.50    2.00    --  107.75  45.00-120.00  166
 20  \w     95.00 178.00   0.50    2.00    --  107.75 125.00   0.00  166
 21  \w     95.00 178.00   0.50    2.00    --  107.75  47.00 115.00  166
 22  \w     95.00 178.00   0.50    2.00    --  107.75 125.00  60.00  166
 23  \w     95.00 178.00   0.50    2.00    --  107.75 125.00 -30.00  166
 24  \w     95.00 178.00   0.50    2.00    --  107.75  45.00  30.00  166
 25  \w     95.00 178.00   0.50    2.00    --  107.75 125.00 -60.00  166
 26  \w     95.00 178.00   0.50    2.00    --  107.75 125.00-150.00  166
 27  \w     94.00 178.00   0.50    2.00    --  107.75  15.00-180.00  168
 28  \w     35.00 112.00   0.50    2.00    --  107.75-125.00  30.00  154
 29  \w     35.00 112.00   0.50    2.00    --  107.75-125.00 120.00  154
 30  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00  90.00   88
 31  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00  60.00   88
 32  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00   0.00   88
 33  \w     35.00  79.00   0.50    2.00    --  107.75 -61.00 -60.00   88
 34  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00-150.00  142
 35  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00-180.00  142
 36  \w     35.00 112.00   0.50    2.00    --  107.75-125.00  60.00  154
 37  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00 120.00  142
 38  \w     35.00 106.00   0.50    2.00    --  107.75 -94.00  90.00  142
 39  \w     35.00 112.00   0.50    2.00    --  107.75-125.00  90.00  154
 40  \w     35.00 119.00   0.50    0.44    --   47.95  47.00 115.00  168
 41  \w    -16.00  28.00   0.50    0.44    --  -47.95  19.00-120.00   88
 42  \w    -43.00 -14.00   0.50    2.00    --  -86.25  45.00 -60.00   58
 43  \w    -86.00 -13.00   0.50    0.44    --  -47.95 125.00 120.00  146
 44  \w   -159.00 -73.00   0.50    2.00    --  -86.25 -47.00 -32.00  172
 45  \w   -120.00 -25.00   0.50    0.44    --  -47.95 -77.00 -30.00  190
 46  \w   -120.00 -73.00   0.50    0.44    --  -47.95-125.00 150.00   94
 47  \w   -120.00 -25.00   0.50    0.44    --  -47.95 -77.00  90.00  190
 48  \w   -120.00 -25.00   0.50    0.44    --  -47.95 -77.00  60.00  190
 49  \w   -120.00 -25.00   0.50    0.44    --  -47.95 -77.00 -90.00  190
 50  \w   -120.00 -25.00   0.50    0.44    --  -47.95 -77.00-180.00  190
;
_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      -0.0618520000
_diffrn_orient_matrix_UB_12      0.0972565000
_diffrn_orient_matrix_UB_13      0.0477961000
_diffrn_orient_matrix_UB_21      0.1565350000
_diffrn_orient_matrix_UB_22      0.0905766000
_diffrn_orient_matrix_UB_23      0.0423741000
_diffrn_orient_matrix_UB_31      -0.0076273000
_diffrn_orient_matrix_UB_32      0.0291569000
_diffrn_orient_matrix_UB_33      -0.0886305000
_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  0.0533
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.340
_diffrn_reflns_theta_min         3.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.83a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM and Hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0534P)^2^+0.5292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6177
_reflns_number_total             7152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03044b2.cif
_cod_data_source_block           bc
_cod_depositor_comments
'Adding full bibliography for 7060907--7060910.cif.'
_cod_original_cell_volume        1706.94(8)
_cod_database_code               7060907
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H16N2O
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C35(H35), C36(H36), C37(H37), C38(H38),
 C40(H40), C42(H42), C43(H43), C44(H44), C45(H45)
;
_shelx_res_checksum              26176
_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.681