Polymorphism and resulting luminescence properties of 1-acetylpyrene
Tchoń, Daniel; Trzybiński, Damian; Wrona-Piotrowicz, Anna; Makal, Anna; CrystEngComm 21 (2019) 5845–; doi:10.1039/C9CE01203F

data_7233410
_publ_section_title
;
 Polymorphism and resulting luminescence properties of 1-acetylpyrene
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5845
_journal_paper_doi               10.1039/C9CE01203F
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C18 H12 O'
_chemical_formula_sum            'C18 H12 O'
_chemical_formula_weight         244.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-03
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-23 deposited with the CCDC.    2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.266(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.3656(14)
_cell_length_b                   7.0662(3)
_cell_length_c                   9.9016(4)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.6220
_cell_measurement_theta_min      2.5550
_cell_volume                     2379.47(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -128.00 -89.00   1.00    1.00    --  -24.46-125.00  90.00   39
  2  \w   -133.00  34.00   1.00    1.00    --  -24.46 -77.00 -90.00  167
  3  \w     40.00  74.00   1.00    1.00    --  -24.46   0.00 -90.00   34
  4  \w   -134.00 -90.00   1.00    1.00    --  -24.46-125.00   0.00   44
  5  \w    -10.00  21.00   1.00    1.00    --  -24.46  77.00 -30.00   31
  6  \w    -47.00  -3.00   1.00    1.00    --  -24.46 125.00 -30.00   44
  7  \w    -56.00 -29.00   1.00    1.00    --  -24.46  77.00 -30.00   27
  8  \w   -134.00   5.00   1.00    1.00    --  -24.46 -57.00 150.00  139
  9  \w     26.00  74.00   1.00    1.00    --  -24.46  77.00 -30.00   48
 10  \w   -107.00  34.00   1.00    1.00    --  -24.46   0.00 -90.00  141
 11  \w     28.00  98.00   1.00    1.00    --   24.46-125.00   0.00   70
 12  \w    -30.00  50.00   1.00    1.00    --   24.46  59.00 135.00   80
 13  \w    -42.00 -13.00   1.00    1.00    --   24.46 125.00   0.00   29
 14  \w    -80.00 -53.00   1.00    7.50    --  -70.50 -50.00 150.00   27
 15  \w   -117.00 -90.00   1.00    7.50    --  -70.50 -50.00 150.00   27
 16  \w    -29.00  -3.00   1.00    7.50    --  -70.50 -50.00 150.00   26
 17  \w    -39.00 -14.00   1.00    7.50    --  -70.50 -77.00 -90.00   25
 18  \w    -98.00 -35.00   1.00    7.50    --  -70.50 178.00   0.00   63
 19  \w   -122.00 -72.00   1.00    7.50    --  -70.50 -77.00 -90.00   50
 20  \w    -71.00 -46.00   1.00    7.50    --  -70.50 -77.00 120.00   25
 21  \w   -177.00-150.00   1.00    7.50    --  -70.50 -77.00 120.00   27
 22  \w    -37.00 -12.00   1.00    7.50    --  -70.50 -77.00 120.00   25
 23  \w     14.00  39.00   1.00    7.50    --   71.47  77.00-180.00   25
 24  \w     14.00  47.00   1.00    7.50    --   71.47  77.00 -30.00   33
 25  \w     70.00 175.00   1.00    7.50    --   71.47  77.00 -30.00  105
 26  \w     54.00 116.00   1.00    7.50    --   71.47  77.00-180.00   62
 27  \w     44.00 149.00   1.00    7.50    --   71.47  63.00 -90.00  105
 28  \w    125.00 178.00   1.00    7.50    --   71.47 111.00  30.00   53
 29  \w     24.00 107.00   1.00    7.50    --   71.47-111.00-150.00   83
 30  \w     16.00 174.00   1.00    7.50    --   71.47  77.00   0.00  158
 31  \w     13.00 177.00   1.00    7.50    --   71.47  77.00  60.00  164
 32  \w     66.00 145.00   1.00    7.50    --   71.47  77.00  30.00   79
 33  \w     14.00  40.00   1.00    7.50    --   71.47  77.00 -60.00   26
 34  \w     50.00 145.00   1.00    7.50    --   71.47  77.00 -60.00   95
 35  \w     14.00  41.00   1.00    7.50    --   71.47  77.00  90.00   27
 36  \w    100.00 126.00   1.00    7.50    --   71.47 111.00-150.00   26
 37  \w     66.00  93.00   1.00    7.50    --   71.47  77.00 -90.00   27
 38  \w     16.00  42.00   1.00    7.50    --   71.47  77.00 -90.00   26
 39  \w     71.00 146.00   1.00    7.50    --   71.47 178.00-120.00   75
 40  \w     56.00 178.00   1.00    7.50    --   71.47  77.00  90.00  122
 41  \w     50.00 174.00   1.00    7.50    --   71.47  77.00 150.00  124
 42  \w     97.00 167.00   1.00    7.50    --   71.47  50.00 120.00   70
 43  \w     15.00  41.00   1.00    7.50    --   71.47  77.00 150.00   26
 44  \w    131.00 159.00   1.00    7.50    --   71.47 111.00-150.00   28
 45  \w    126.00 175.00   1.00    7.50    --   71.47 111.00 120.00   49
 46  \w     13.00  43.00   1.00    7.50    --   71.47  79.00-119.22   30
 47  \w     59.00 122.00   1.00    7.50    --   71.47  77.00-150.00   63
 48  \w    117.00 176.00   1.00    7.50    --   71.47  77.00-180.00   59
 49  \w     14.00  45.00   1.00    7.50    --   71.47  80.00 106.28   31
 50  \w     13.00  40.00   1.00    7.50    --   71.47  77.00-150.00   27
 51  \w     59.00  86.00   1.00   15.00    --  118.48  67.00  60.00   27
 52  \w     96.00 124.00   1.00   15.00    --  118.48  67.00 120.00   28
 53  \w     59.00  87.00   1.00   15.00    --  118.48  67.00 120.00   28
 54  \w     92.00 118.00   1.00   15.00    --  118.48-125.00 -60.00   26
 55  \w    139.00 178.00   1.00   15.00    --  118.48  99.00-150.00   39
 56  \w     62.00 103.00   1.00   15.00    --  118.48  67.00   0.00   41
 57  \w     43.00  72.00   1.00   15.00    --  118.48-125.00 -60.00   29
 58  \w    102.00 138.00   1.00   15.00    --  118.48  99.00-150.00   36
 59  \w     61.00 177.00   1.00   15.00    --  118.48  77.00   0.00  116
 60  \w    109.00 136.00   1.00   15.00    --  118.48  67.00  60.00   27
 61  \w     60.00 149.00   1.00   15.00    --  118.48  77.00-120.00   89
 62  \w      9.00 127.00   1.00   15.00    --  118.48 -77.00-180.00  118
 63  \w     37.00 118.00   1.00   15.00    --  118.48-125.00  90.00   81
 64  \w    124.00 149.00   1.00   15.00    --  118.48 178.00   0.00   25
 65  \w     57.00 112.00   1.00   15.00    --  118.48 178.00   0.00   55
 66  \w    151.00 178.00   1.00   15.00    --  118.48  77.00-180.00   27
 67  \w     60.00 174.00   1.00   15.00    --  118.48  77.00 -90.00  114
 68  \w     61.00 138.00   1.00   15.00    --  118.48  76.00 -47.37   77
 69  \w     60.00 143.00   1.00   15.00    --  118.48  77.00-180.00   83
 70  \w     60.00 172.00   1.00   15.00    --  118.48  77.00 -30.00  112
 71  \w     60.00 178.00   1.00   15.00    --  118.48  77.00  60.00  118
 72  \w     60.00 147.00   1.00   15.00    --  118.48  77.00-150.00   87
 73  \w     85.00 110.00   1.00   15.00    --  118.48 -99.00  30.00   25
 74  \w     70.00 128.00   1.00   15.00    --  118.48 178.00  90.00   58
 75  \w    132.00 178.00   1.00   15.00    --  118.48  77.00  90.00   46
 76  \w     50.00  77.00   1.00   15.00    --  118.48 -99.00  30.00   27
 77  \w     61.00 126.00   1.00   15.00    --  118.48  77.00  90.00   65
 78  \w     45.00 102.00   1.00   15.00    --  118.48 -99.00 -30.00   57
 79  \w    110.00 178.00   1.00   15.00    --  118.48 125.00-120.00   68
 80  \w      8.00  34.00   1.00   15.00    --  118.48 -99.00 -30.00   26
 81  \w    124.00 171.00   1.00   15.00    --  118.48  67.00-180.00   47
 82  \w     59.00 107.00   1.00   15.00    --  118.48  67.00-180.00   48
 83  \w     59.00  89.00   1.00   15.00    --  118.48  67.00  30.00   30
 84  \w    104.00 129.00   1.00   15.00    --  118.48  67.00-150.00   25
 85  \w     60.00  87.00   1.00   15.00    --  118.48  67.00-150.00   27
 86  \w     58.00 102.00   1.00   15.00    --  118.48 -99.00 -90.00   44
 87  \w     59.00 104.00   1.00   15.00    --  118.48  67.00 150.00   45
 88  \w     88.00 113.00   1.00   15.00    --  118.48  67.00  90.00   25
 89  \w     59.00  85.00   1.00   15.00    --  118.48  67.00  90.00   26
 90  \w     59.00  85.00   1.00   15.00    --  118.48  67.00-120.00   26
 91  \w     14.00  50.00   1.00   15.00    --  118.48 -67.00  90.00   36
 92  \w     66.00 101.00   1.00   15.00    --  118.48 -67.00  90.00   35
 93  \w    123.00 149.00   1.00   15.00    --  118.48 -67.00  90.00   26
 94  \w     59.00  85.00   1.00   15.00    --  118.48  67.00 -60.00   26
 95  \w     60.00 175.00   1.00   15.00    --  118.48  77.00 150.00  115
 96  \w     77.00 118.00   1.00   15.00    --  118.48-125.00-150.00   41
 97  \w     91.00 118.00   1.00   15.00    --  118.48  67.00 -90.00   27
 98  \w     59.00  85.00   1.00   15.00    --  118.48  67.00 -90.00   26
 99  \w    102.00 167.00   1.00   15.00    --  118.48  77.00 -60.00   65
100  \w     60.00 160.00   1.00   15.00    --  118.48  77.00 120.00  100
101  \w     60.00  98.00   1.00   15.00    --  118.48  77.00 -60.00   38
102  \w    109.00 134.00   1.00   15.00    --  118.48  67.00   0.00   25
103  \w     60.00 152.00   1.00   15.00    --  118.48  75.00  28.07   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0131030115
_diffrn_orient_matrix_UB_12      -0.2034789927
_diffrn_orient_matrix_UB_13      -0.0396032163
_diffrn_orient_matrix_UB_21      -0.0289557454
_diffrn_orient_matrix_UB_22      0.0771150909
_diffrn_orient_matrix_UB_23      -0.1207023038
_diffrn_orient_matrix_UB_31      0.0322784022
_diffrn_orient_matrix_UB_32      -0.0134785643
_diffrn_orient_matrix_UB_33      -0.0926323569
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14275
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.689
_diffrn_reflns_theta_min         2.598
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0907P)^2^+1.0862P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                4105
_reflns_number_total             4310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01203f2.cif
_cod_data_source_block           abscc
_cod_depositor_comments
'Adding full bibliography for 7233408--7233410.cif.'
_cod_original_cell_volume        2379.47(18)
_cod_database_code               7233410
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C20 H14 O2'
_chemical_oxdiff_usercomment     '100 K, colourless plate'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.810
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.472(4)
 0.528(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C3A-H3A = C3B-H3B
 0.93 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B),
 C13B(H13B), C14B(H14B)
4.b Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_shelx_res_checksum              63017
_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 3.406
_oxdiff_exptl_absorpt_empirical_full_min 0.603