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_7060908
_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         'C25 H16 N2 O'
_chemical_formula_sum            'C25 H16 N2 O'
_chemical_formula_weight         360.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.04500(10)
_cell_length_b                   20.4122(2)
_cell_length_c                   17.8760(2)
_cell_measurement_reflns_used    23696
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.5020
_cell_measurement_theta_min      3.3180
_cell_volume                     3566.29(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (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      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 0.992
_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    -81.00   3.00   0.50    0.90    --  -49.47 105.00 123.00  168
  2  \w     18.00  84.00   0.50    0.90    --   49.47-105.00  22.00  132
  3  \w    -81.00 -18.00   0.50    5.00    --  -90.00 105.00 123.00  126
  4  \w   -161.00 -83.00   0.50    5.00    --  -90.00-105.00  22.00  156
  5  \w    105.00 178.00   0.50    5.00    --  111.50 105.00 123.00  146
  6  \w     41.00 107.00   0.50    5.00    --  111.50-105.00  22.00  132
  7  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00 120.00   80
  8  \w    -59.00  23.00   0.50    0.90    --  -49.47  57.00  90.00  164
  9  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00 -30.00   80
 10  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00 150.00   80
 11  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00 -60.00   80
 12  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00-180.00   80
 13  \w   -121.00 -37.00   0.50    0.90    --  -49.47 -57.00   0.00  168
 14  \w    -16.00  24.00   0.50    0.90    --  -49.47  19.00  30.00   80
 15  \w     34.00  95.00   0.50    0.90    --   49.47-125.00  90.00  122
 16  \w   -162.00 -82.00   0.50    5.00    --  -90.00 -30.00  30.00  160
 17  \w    -65.00 -18.00   0.50    5.00    --  -90.00  61.00 -60.00   94
 18  \w    -65.00 -18.00   0.50    5.00    --  -90.00  61.00  90.00   94
 19  \w    -65.00 -18.00   0.50    5.00    --  -90.00  61.00 150.00   94
 20  \w   -161.00 -71.00   0.50    5.00    --  -90.00 -73.00  73.76  180
 21  \w     95.00 178.00   0.50    5.00    --  111.50 125.00-180.00  166
 22  \w    104.00 178.00   0.50    5.00    --  111.50  15.00 -30.00  148
 23  \w     41.00 106.00   0.50    5.00    --  111.50 -93.00  45.28  130
 24  \w    104.00 178.00   0.50    5.00    --  111.50  15.00 120.00  148
 25  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00 -30.00   76
 26  \w     41.00 111.00   0.50    5.00    --  111.50-125.00  60.00  140
 27  \w     97.00 178.00   0.50    5.00    --  111.50  61.00-120.00  162
 28  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00 -30.00  128
 29  \w     41.00 111.00   0.50    5.00    --  111.50-125.00   0.00  140
 30  \w     91.00 178.00   0.50    5.00    --  111.50  77.00  60.00  174
 31  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00 -60.00   76
 32  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00 -60.00  128
 33  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00  90.00  128
 34  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00 120.00  128
 35  \w     97.00 178.00   0.50    5.00    --  111.50  61.00-180.00  162
 36  \w     97.00 178.00   0.50    5.00    --  111.50  61.00 -30.00  162
 37  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00 -90.00   76
 38  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00  90.00   76
 39  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00-150.00  128
 40  \w     41.00 111.00   0.50    5.00    --  111.50-125.00 -60.00  140
 41  \w    102.00 178.00   0.50    5.00    --  111.50  45.00 -90.00  152
 42  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00 120.00   76
 43  \w     41.00 106.00   0.50    5.00    --  111.50-100.00 -98.38  130
 44  \w     97.00 178.00   0.50    5.00    --  111.50  61.00 -60.00  162
 45  \w     95.00 178.00   0.50    5.00    --  111.50 125.00-150.00  166
 46  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00 150.00  128
 47  \w     41.00 111.00   0.50    5.00    --  111.50-125.00 -90.00  140
 48  \w     41.00 111.00   0.50    5.00    --  111.50-125.00 -30.00  140
 49  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00-180.00  128
 50  \w     41.00  79.00   0.50    5.00    --  111.50 -61.00-180.00   76
 51  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00  30.00  128
 52  \w     45.00  94.00   0.50    5.00    --  111.50 -94.00  60.00   98
 53  \w    102.00 177.00   0.50    5.00    --  111.50  45.00-150.00  150
;
_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      0.1466111000
_diffrn_orient_matrix_UB_12      0.0213602000
_diffrn_orient_matrix_UB_13      -0.0011739000
_diffrn_orient_matrix_UB_21      -0.0311339000
_diffrn_orient_matrix_UB_22      0.0696066000
_diffrn_orient_matrix_UB_23      0.0245490000
_diffrn_orient_matrix_UB_31      0.0488230000
_diffrn_orient_matrix_UB_32      -0.0197657000
_diffrn_orient_matrix_UB_33      0.0851156000
_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  0.0699
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            88647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.786
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.96a (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    1.342
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1337P)^2^+0.5485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6200
_reflns_number_total             7713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03044b2.cif
_cod_data_source_block           py-bc
_cod_depositor_comments
'Adding full bibliography for 7060907--7060910.cif.'
_cod_database_code               7060908
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H16N2O
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C33(H33)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C36(H36), C37(H37), C39(H39), C40(H40),
 C42(H42), C43(H43), C44(H44), C46(H46), C47(H47)
;
_shelx_res_checksum              39693
_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 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.457