Comparative study of the photophysical and crystallographic properties of 4-(9H-pyreno[4,5-d]imidazol-10-yl)phenol and its alkylated derivatives
Tabasi, Zahra A.; Walsh, Joshua C.; Bodwell, Graham J.; Thompson, David W.; Zhao, Yuming; New Journal of Chemistry 45 (2021) 7647–7658; doi:10.1039/D1NJ01102B

data_7060541
_publ_section_title
;
 Comparative study of the photophysical and crystallographic properties of
 4-(9H-pyreno[4,5-d]imidazol-10-yl)phenol and its alkylated derivatives
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7647
_journal_page_last               7658
_journal_paper_doi               10.1039/D1NJ01102B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C33 H34 N2 O, 2(H2 O)'
_chemical_formula_sum            'C33 H38 N2 O3'
_chemical_formula_weight         510.65
_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             2019-09-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2019-12-18 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                87.414(3)
_cell_angle_beta                 79.965(3)
_cell_angle_gamma                63.475(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9659(3)
_cell_length_b                   8.9998(3)
_cell_length_c                   19.2836(7)
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0500
_cell_measurement_theta_min      5.4890
_cell_volume                     1369.99(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 0.972
_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     29.00 118.00   0.50    2.00    --   47.20  75.00 -55.00  178
  2  \w     86.00 169.00   0.50   10.00    --  107.75  75.00 -55.00  166
  3  \w    151.00 176.00   0.50   10.00    --  107.75  45.00 -90.00   50
  4  \w    135.00 162.00   0.50   10.00    --  107.75 125.00-120.00   54
  5  \w     98.00 125.00   0.50   10.00    --  107.75  30.00 -90.00   54
  6  \w     96.00 178.00   0.50   10.00    --  107.75  45.00-120.00  164
  7  \w     97.00 129.00   0.50   10.00    --  107.75 125.00-120.00   64
  8  \w     97.00 133.00   0.50   10.00    --  107.75 125.00 -90.00   72
  9  \w     91.00 178.00   0.50   10.00    --  107.75  61.00 -30.00  174
 10  \w     95.00 146.00   0.50   10.00    --  107.75  45.00 -90.00  102
 11  \w     92.00 160.00   0.50   10.00    --  107.75  61.00-150.00  136
 12  \w     62.00 107.00   0.50   10.00    --  107.75-102.00 -88.30   90
 13  \w     82.00 109.00   0.50   10.00    --  107.75-125.00 -30.00   54
 14  \w     74.00 105.00   0.50   10.00    --  107.75 -94.00   0.00   62
 15  \w     65.00  96.00   0.50   10.00    --  107.75 -94.00 -30.00   62
 16  \w     52.00 108.00   0.50   10.00    --  107.75-125.00 -90.00  112
 17  \w     72.00 104.00   0.50   10.00    --  107.75 -94.00-180.00   64
 18  \w     37.00 106.00   0.50   10.00    --  107.75 -94.00 -60.00  138
 19  \w     42.00  69.00   0.50   10.00    --  107.75 -94.00   0.00   54
 20  \w     46.00  79.00   0.50   10.00    --  107.75 -61.00  60.00   66
 21  \w     76.00 106.00   0.50   10.00    --  107.75 -94.00 120.00   60
 22  \w     80.00 109.00   0.50   10.00    --  107.75-117.00 102.25   58
 23  \w     83.00 110.00   0.50   10.00    --  107.75-125.00 150.00   54
 24  \w     71.00  98.00   0.50   10.00    --  107.75-125.00 120.00   54
 25  \w     61.00  87.00   0.50   10.00    --  107.75 -75.00 176.00   52
 26  \w     45.00  71.00   0.50   10.00    --  107.75-125.00 150.00   52
 27  \w     41.00  70.00   0.50   10.00    --  107.75-117.00 102.25   58
 28  \w     40.00 105.00   0.50   10.00    --  107.75-125.00  90.00  130
 29  \w     35.00  62.00   0.50   10.00    --  107.75-125.00 120.00   54
 30  \w     39.00  69.00   0.50   10.00    --  107.75 -94.00 120.00   60
 31  \w     36.00 100.00   0.50   10.00    --  107.75 -94.00 150.00  128
 32  \w     37.00  63.00   0.50   10.00    --  107.75 -61.00   0.00   52
 33  \w     41.00  69.00   0.50   10.00    --  107.75 -61.00 -30.00   56
 34  \w     40.00  65.00   0.50   10.00    --  107.75 -61.00 -90.00   50
 35  \w     37.00  64.00   0.50   10.00    --  107.75-125.00 -30.00   54
 36  \w    -16.00  27.00   0.50    2.00    --   47.20 -19.00  60.00   86
 37  \w     12.00  58.00   0.50    2.00    --   47.20 -75.00 176.00   92
 38  \w     -2.00  23.00   0.50    2.00    --  -47.20  19.00 -60.00   50
 39  \w    -15.00  22.00   0.50    2.00    --  -47.20  19.00-120.00   74
 40  \w    -30.00  26.00   0.50    2.00    --  -47.20  37.00 -90.00  112
 41  \w    -42.00 -15.00   0.50   10.00    --  -86.25  45.00-120.00   54
 42  \w    -68.00  -8.00   0.50    2.00    --  -47.20  75.00 -55.00  120
 43  \w    -74.00 -47.00   0.50   10.00    --  -86.25  75.00 -55.00   54
 44  \w    -43.00 -14.00   0.50   10.00    --  -86.25  45.00  90.00   58
 45  \w    -43.00 -18.00   0.50   10.00    --  -86.25  45.00 120.00   50
 46  \w   -119.00 -32.00   0.50    2.00    --  -47.20 -75.00 176.00  174
 47  \w    140.00 167.00   0.50   10.00    --  107.75 125.00 150.00   54
 48  \w    135.00 160.00   0.50   10.00    --  107.75  77.00 150.00   50
 49  \w    106.00 136.00   0.50   10.00    --  107.75 125.00 150.00   60
 50  \w     91.00 118.00   0.50   10.00    --  107.75  77.00 150.00   54
 51  \w     35.00  60.00   0.50   10.00    --  107.75 -61.00-180.00   50
 52  \w   -118.00 -74.00   0.50    2.00    --  -47.20-125.00 -90.00   88
 53  \w   -131.00-106.00   0.50   10.00    --  -86.25 -75.00 176.00   50
;
_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      0.0672291000
_diffrn_orient_matrix_UB_12      -0.1726522000
_diffrn_orient_matrix_UB_13      0.0323266000
_diffrn_orient_matrix_UB_21      0.0538495000
_diffrn_orient_matrix_UB_22      0.0664487000
_diffrn_orient_matrix_UB_23      0.0585301000
_diffrn_orient_matrix_UB_31      -0.1748971000
_diffrn_orient_matrix_UB_32      0.0492695000
_diffrn_orient_matrix_UB_33      0.0460492000
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.555
_diffrn_reflns_theta_min         2.328
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
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    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0772P)^2^+0.5058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5220
_reflns_number_total             5677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01102b2.cif
_cod_data_source_block           za58-2-2
_cod_depositor_comments
'Adding full bibliography for 7060539--7060541.cif.'
_cod_database_code               7060541
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H34 N2 O'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.913
_diffrn_oxdiff_digest_frames
;
01fa90c89af967b14fd43487be4a223f7200027f15a
;
_diffrn_oxdiff_digest_hkl
;
016fa1f34f2c55f557aab61554c0ba00e572e8
;
_reflns_odcompleteness_completeness 99.46
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              39608
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.585