Crystal morphology fixed by interplay of π-stacking and hydrogen bonds – the case of 1-hydroxypyrene
Gajda, Roman; Domański, Mateusz A.; Malinska, Maura; Makal, Anna; CrystEngComm 21 (2019) 1701–; doi:10.1039/C8CE02130A

data_7232298
_publ_section_title
;
 Crystal morphology fixed by interplay of \p-stacking and hydrogen bonds
 -- the case of 1-hydroxypyrene
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1701
_journal_paper_doi               10.1039/C8CE02130A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_chemical_name_systematic
;
 1-hydroxypyrene
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-21 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.015(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8662(7)
_cell_length_b                   4.58166(18)
_cell_length_c                   16.6568(7)
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    300.00(10)
_cell_measurement_theta_max      74.5320
_cell_measurement_theta_min      2.6530
_cell_volume                     1058.21(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 54

  2 omega    5.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000   30.0000  120.0000 144

  3 omega   98.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 26

  4 omega  138.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000   30.0000 37

  5 omega  147.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 29

  6 omega  132.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 40

  7 omega  120.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000  120.0000 57

  8 omega  113.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  111.0000   30.0000 65

  9 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000  -90.0000 26

 10 omega  116.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  125.0000 -150.0000 33

 11 omega   75.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000 -180.0000 97

 12 omega  100.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 55

 13 omega   75.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   37.0000   90.0000 96

 14 omega   99.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   77.0000   60.0000 27

 15 omega   83.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000   50.0000  120.0000 44

 16 omega   44.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -63.0000   90.0000 110

 17 omega   84.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  150.0000 27

 18 omega   32.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000   90.0000 83

 19 omega   60.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -30.0000 55

 20 omega   67.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 45

 21 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000  -90.0000 27

 22 omega   31.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000  -91.0000  -30.0000 48

 23 omega   30.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      121.0000 -111.0000 -120.0000 42

 24 omega   18.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.5000  -94.0000  -60.0000 90

 25 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 32

 26 omega -117.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -120.0000 35

 27 omega -150.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  -94.0000 -150.0000 62

 28 omega  -90.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000   45.0000  -90.0000 121

 29 omega  -86.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 41

 30 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.5000  125.0000  150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1007565000
_diffrn_orient_matrix_UB_12      0.1408774000
_diffrn_orient_matrix_UB_13      -0.0033863000
_diffrn_orient_matrix_UB_21      0.0001848000
_diffrn_orient_matrix_UB_22      0.0287714000
_diffrn_orient_matrix_UB_23      0.0921545000
_diffrn_orient_matrix_UB_31      0.0466987000
_diffrn_orient_matrix_UB_32      -0.3041100000
_diffrn_orient_matrix_UB_33      0.0071086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6289
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         2.653
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_density_diffrn    1.370
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4945
_exptl_crystal_size_mid          0.1744
_exptl_crystal_size_min          0.0593
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.459(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0521
_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^)+(0.1004P)^2^+0.0100P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.687
_reflns_number_gt                2753
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02130a2.cif
_cod_data_source_block           t300
_cod_depositor_comments
'Adding full bibliography for 7232276--7232298.cif.'
_cod_database_code               7232298
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C16 H10 O1'
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.541(4)
 0.459(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34)
3.b Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'