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_7060910
_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_absolute_configuration ad
_chemical_formula_moiety         'C29 H18 N2 O, C H Cl3'
_chemical_formula_sum            'C30 H19 Cl3 N2 O'
_chemical_formula_weight         529.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-14 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.942(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8515(2)
_cell_length_b                   21.8040(12)
_cell_length_c                   11.5794(5)
_cell_measurement_reflns_used    7135
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      3.7820
_cell_volume                     1224.19(10)
_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 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 0.996
_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    -11.00  24.00   0.50    8.00    --  -49.25  11.00 -83.00   70
  2  \w   -121.00 -42.00   0.50    8.00    --  -49.25 -11.00 103.00  158
  3  \w    -23.00  25.00   0.50    8.00    --   49.25 -11.00 103.00   96
  4  \w     42.00 122.00   0.50    8.00    --   49.25  11.00 -83.00  160
  5  \w   -162.00 -82.00   0.50   25.00    --  -90.00 -11.00 103.00  160
  6  \w    104.00 178.00   0.50   25.00    --  111.50  11.00 -83.00  148
  7  \w    -86.00 -13.00   0.50    5.00    --  -49.25 125.00  90.00  146
  8  \w    -16.00  24.00   0.50    5.00    --  -49.25  19.00-150.00   80
  9  \w    -86.00 -13.00   0.50    5.00    --  -49.25 125.00-150.00  146
 10  \w    -16.00  24.00   0.50    5.00    --  -49.25  19.00 -60.00   80
 11  \w    -65.00 -18.00   0.50   14.00    --  -90.00  61.00  30.00   94
 12  \w   -161.00 -81.00   0.50   14.00    --  -90.00 -45.00-150.00  160
 13  \w     41.00 105.00   0.50   14.00    --  111.50 -94.00 -90.00  128
 14  \w     41.00 105.00   0.50   14.00    --  111.50 -94.00 -30.00  128
 15  \w     41.00  79.00   0.50   14.00    --  111.50 -61.00 120.00   76
 16  \w     41.00 105.00   0.50   14.00    --  111.50 -94.00  30.00  128
 17  \w     41.00 111.00   0.50   14.00    --  111.50-125.00-180.00  140
 18  \w    102.00 178.00   0.50   14.00    --  111.50  45.00-180.00  152
 19  \w    104.00 178.00   0.50   14.00    --  111.50  30.00 150.00  148
 20  \w    102.00 178.00   0.50   14.00    --  111.50  45.00-120.00  152
 21  \w     41.00 105.00   0.50   14.00    --  111.50 -94.00   0.00  128
 22  \w    104.00 178.00   0.50   14.00    --  111.50  15.00  30.00  148
 23  \w     41.00  79.00   0.50   14.00    --  111.50 -61.00-120.00   76
 24  \w     41.00  79.00   0.50   14.00    --  111.50 -61.00  30.00   76
 25  \w     41.00  79.00   0.50   14.00    --  111.50 -61.00 -90.00   76
 26  \w     41.00 105.00   0.50   14.00    --  111.50 -94.00-150.00  128
 27  \w   -120.00 -28.00   0.50    5.00    --  -49.25 -77.00  60.00  184
 28  \w   -120.00 -50.00   0.50    5.00    --  -49.25 -77.00-180.00  140
 29  \w     37.00 121.00   0.50    5.00    --   49.25  57.00 -30.00  168
 30  \w     51.00  76.00   0.50    5.00    --   49.43  77.00-180.00   50
 31  \w    -66.00 -40.00   0.50    5.00    --  -49.43 -44.00 -15.23   52
 32  \w    -68.00 -42.00   0.50    5.00    --  -49.43 -37.00 -30.00   52
 33  \w    -63.00 -37.00   0.50    5.00    --  -49.43 -77.00 -30.00   52
 34  \w    -54.00 -29.00   0.50    5.00    --  -49.43 -77.00   0.00   50
 35  \w    -55.00 -29.00   0.50    5.00    --  -49.43 -77.00  30.00   52
 36  \w     44.00  71.00   0.50    5.00    --   49.43  37.00 -30.00   54
 37  \w     43.00  70.00   0.50    5.00    --   49.43  37.00  60.00   54
 38  \w     45.00  96.00   0.50    5.00    --   49.43  19.00   0.00  102
 39  \w     44.00  70.00   0.50    5.00    --   49.43  37.00  30.00   52
 40  \w     30.00  57.00   0.50    5.00    --   49.43  77.00  60.00   54
 41  \w   -100.00 -74.00   0.50   14.00    --  -90.00 -64.00 -30.19   52
 42  \w    -96.00 -70.00   0.50   14.00    --  -90.00 -77.00  30.00   52
 43  \w    -95.00 -69.00   0.50   14.00    --  -90.00 -77.00   0.00   52
 44  \w    -99.00 -73.00   0.50   14.00    --  -90.00 -77.00 -30.00   52
 45  \w    -96.00 -70.00   0.50   14.00    --  -90.00 -75.00  42.89   52
 46  \w    -97.00 -71.00   0.50   14.00    --  -90.00 -77.00 -60.00   52
 47  \w    -94.00 -69.00   0.50   14.00    --  -90.00 -77.00  60.00   50
 48  \w   -101.00 -75.00   0.50   14.00    --  -90.00 -62.00  -2.97   52
 49  \w   -103.00 -77.00   0.50   14.00    --  -90.00 -63.00  -4.47   52
 50  \w    -99.00 -73.00   0.50   14.00    --  -90.00 -69.00  66.83   52
 51  \w   -100.00 -74.00   0.50   14.00    --  -90.00 -64.00  34.06   52
 52  \w   -102.00 -76.00   0.50   14.00    --  -90.00 -61.00  43.60   52
 53  \w    -95.00 -70.00   0.50   14.00    --  -90.00 -74.00 -21.25   50
 54  \w   -100.00 -74.00   0.50   14.00    --  -90.00 -74.00  21.83   52
 55  \w    -99.00 -74.00   0.50   14.00    --  -90.00 -66.00  56.36   50
 56  \w    -97.00 -72.00   0.50   14.00    --  -90.00 -75.00  35.25   50
 57  \w    -98.00 -72.00   0.50   14.00    --  -90.00 -71.00 -62.23   52
 58  \w    -96.00 -71.00   0.50   14.00    --  -90.00 -73.00 -48.71   50
 59  \w    -97.00 -71.00   0.50   14.00    --  -90.00 -77.00  90.00   52
 60  \w    -96.00 -71.00   0.50   14.00    --  -90.00 -72.00  -2.84   50
 61  \w    104.00 138.00   0.50   14.00    --  111.50  61.00  60.00   68
 62  \w    153.00 178.00   0.50   14.00    --  111.50  61.00  30.00   50
 63  \w     97.00 123.00   0.50   14.00    --  111.50  61.00  30.00   52
 64  \w     53.00  79.00   0.50   14.00    --  111.50 -61.00-180.00   52
 65  \w    153.00 178.00   0.50   14.00    --  111.50  61.00 -30.00   50
 66  \w     97.00 123.00   0.50   14.00    --  111.50  61.00 -30.00   52
 67  \w     93.00 119.00   0.50   14.00    --  111.50  77.00 -30.00   52
 68  \w    153.00 178.00   0.50   14.00    --  111.50  77.00 -60.00   50
 69  \w     93.00 102.50   0.50   14.00    --  111.50  77.00 -60.00   19
;
_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      0.1428603000
_diffrn_orient_matrix_UB_12      -0.0096721000
_diffrn_orient_matrix_UB_13      0.1194612000
_diffrn_orient_matrix_UB_21      -0.2835199000
_diffrn_orient_matrix_UB_22      -0.0014477000
_diffrn_orient_matrix_UB_23      0.0559588000
_diffrn_orient_matrix_UB_31      -0.0139426000
_diffrn_orient_matrix_UB_32      -0.0699781000
_diffrn_orient_matrix_UB_33      -0.0176289000
_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  0.0808
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23474
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.968
_diffrn_reflns_theta_min         3.820
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68197
_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    1.437
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4748
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0694
_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^)+(0.1289P)^2^+0.4614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2025
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                3922
_reflns_number_total             4748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03044b2.cif
_cod_data_source_block           py-np
_cod_depositor_comments
'Adding full bibliography for 7060907--7060910.cif.'
_cod_database_code               7060910
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C29H18N2OCHCl3
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.532
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.97(4)
 0.03(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
 Cl1A-C1A \\sim Cl3A-C1A \\sim Cl2A-C1A \\sim Cl2B-C1B \\sim Cl3B-C1B \\sim
Cl1B-C1B
 with sigma of 0.02
4. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C1B)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C1A)=Sof(H1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C12(H12)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26)
;
_shelx_res_checksum              49503
_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 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.436