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_7060909
_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         '2(C27 H18 N2 O), 3(C H Cl3)'
_chemical_formula_sum            'C57 H39 Cl9 N4 O2'
_chemical_formula_weight         1130.97
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                92.4379(16)
_cell_angle_beta                 94.2137(15)
_cell_angle_gamma                91.8446(16)
_cell_formula_units_Z            1
_cell_length_a                   10.3742(2)
_cell_length_b                   11.1000(2)
_cell_length_c                   11.2768(2)
_cell_measurement_reflns_used    16301
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2750
_cell_measurement_theta_min      3.9220
_cell_volume                     1293.07(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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  (Sheldrick, 2015)'
_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     31.00 120.00   0.50    0.06    --   47.95  63.00 -69.00  178
  2  \w     91.00 178.00   0.50    0.24    --  107.75  63.00 -69.00  174
  3  \w     95.00 178.00   0.50    0.24    --  107.75 125.00-120.00  166
  4  \w     95.00 178.00   0.50    0.24    --  107.75  45.00 -30.00  166
  5  \w     95.00 178.00   0.50    0.24    --  107.75  30.00-120.00  166
  6  \w     95.00 178.00   0.50    0.24    --  107.75  45.00 -90.00  166
  7  \w     95.00 178.00   0.50    0.24    --  107.75  30.00  60.00  166
  8  \w     95.00 178.00   0.50    0.24    --  107.75  30.00-150.00  166
  9  \w     95.00 178.00   0.50    0.24    --  107.75  30.00-180.00  166
 10  \w     35.00 112.00   0.50    0.24    --  107.75-125.00 -60.00  154
 11  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00  90.00  142
 12  \w     39.00 118.00   0.50    0.24    --  107.75-133.00  -3.95  158
 13  \w     35.00  82.00   0.50    0.24    --  107.75 -63.00 153.00   94
 14  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00  60.00  142
 15  \w     35.00  79.00   0.50    0.24    --  107.75 -61.00 -60.00   88
 16  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00-120.00  142
 17  \w     35.00 131.00   0.50    0.24    --  107.75 -77.00-150.00  192
 18  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00  30.00  142
 19  \w     35.00 112.00   0.50    0.24    --  107.75-125.00  60.00  154
 20  \w     35.00 131.00   0.50    0.24    --  107.75 -77.00  90.00  192
 21  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00 -30.00  142
 22  \w     35.00  79.00   0.50    0.24    --  107.75 -61.00  30.00   88
 23  \w     35.00  79.00   0.50    0.24    --  107.75 -61.00 -30.00   88
 24  \w     35.00 131.00   0.50    0.24    --  107.75 -77.00 -90.00  192
 25  \w     35.00 112.00   0.50    0.24    --  107.75-125.00  90.00  154
 26  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00 120.00  142
 27  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00 150.00  142
 28  \w     35.00 112.00   0.50    0.24    --  107.75-125.00  30.00  154
 29  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00 -60.00  142
 30  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00-150.00  142
 31  \w     35.00 106.00   0.50    0.24    --  107.75 -94.00-180.00  142
 32  \w     25.00 120.00   0.50    0.06    --   47.95  77.00-180.00  190
 33  \w    -34.00  25.00   0.50    0.06    --  -47.95  37.00-120.00  118
 34  \w    -65.00  25.00   0.50    0.06    --  -47.95  63.00 -69.00  180
 35  \w    -43.00 -14.00   0.50    0.24    --  -86.25  45.00  60.00   58
 36  \w    -43.00 -14.00   0.50    0.24    --  -86.25  45.00 120.00   58
 37  \w    -16.00  28.00   0.50    0.06    --  -47.95  19.00 150.00   88
 38  \w    -24.00  65.00   0.50    0.06    --   47.95 -63.00 153.00  178
 39  \w    -68.00 -13.00   0.50    0.24    --  -86.25  63.00 -69.00  110
 40  \w    -86.00 -13.00   0.50    0.06    --  -47.95 125.00  30.00  146
 41  \w   -119.00 -33.00   0.50    0.06    --  -47.95 -57.00 -30.00  172
 42  \w   -120.00 -31.00   0.50    0.06    --  -47.95 -63.00 153.00  178
 43  \w   -120.00 -25.00   0.50    0.06    --  -47.95 -77.00  60.00  190
 44  \w   -119.00 -33.00   0.50    0.06    --  -47.95 -57.00  90.00  172
 45  \w   -120.00 -62.00   0.50    0.06    --  -47.95 -77.00 -60.00  116
 46  \w   -120.00 -25.00   0.50    0.06    --  -47.95 -77.00-120.00  190
 47  \w   -159.00 -69.00   0.50    0.24    --  -86.25 -63.00 153.00  180
;
_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      -0.1145434000
_diffrn_orient_matrix_UB_12      0.0305444000
_diffrn_orient_matrix_UB_13      0.0740721000
_diffrn_orient_matrix_UB_21      0.0192727000
_diffrn_orient_matrix_UB_22      -0.1164710000
_diffrn_orient_matrix_UB_23      0.0677520000
_diffrn_orient_matrix_UB_31      0.0933500000
_diffrn_orient_matrix_UB_32      0.0694644000
_diffrn_orient_matrix_UB_33      0.0934710000
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32585
_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         77.373
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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    1.452
_exptl_crystal_description       irregular
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.969
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0015(4)
_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   1.066
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5420
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.8660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4780
_reflns_number_total             5420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03044b2.cif
_cod_data_source_block           np
_cod_depositor_comments
'Adding full bibliography for 7060907--7060910.cif.'
_cod_database_code               7060909
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H18N2O
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.432
_reflns_odcompleteness_completeness 99.77
_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 C(H,H) groups, All N(H) groups
2. Restrained distances
 C2S-Cl4S = C2S-Cl6S = C2S-Cl5S
 1.78 with sigma of 0.02
 C2S-Cl4S \\sim C2S-Cl6S \\sim C2S-Cl5S
 with sigma of 0.02
 Cl4S-Cl6S \\sim Cl6S-Cl5S \\sim Cl5S-Cl4S
 with sigma of 0.04
3. Rigid bond restraints
 Cl4S, Cl5S, Cl6S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Cl4S \\sim Cl5S \\sim Cl6S \\sim C2S: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Cl4S \\sim Cl5S \\sim Cl6S: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
5. Rigid body (RIGU) restrains
 Cl4S, Cl5S, Cl6S, C2S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Cl4S(0.5) Cl5S(0.5) Cl6S(0.5) C2S(0.5) H2S(0.5)
;
_shelx_res_checksum              44321
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.454