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_7232276
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H10 O'
_chemical_formula_sum            'C16 H10 O'
_chemical_formula_weight         218.24
_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   mixed
_audit_creation_date             2019-01-14
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-22 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.096(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8179(5)
_cell_length_b                   4.53024(16)
_cell_length_c                   16.5413(6)
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.4810
_cell_measurement_theta_min      2.4410
_cell_volume                     1035.46(6)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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     -3.00  97.00   1.00   20.00    --   27.00  77.00 -90.00  100
  2  \w     21.00 103.00   1.00   20.00    --   27.00-160.00  60.00   82
  3  \w    -20.00  69.00   1.00   20.00    --   27.00 -99.00 150.00   89
  4  \w     -3.00  97.00   1.00   20.00    --   27.00  77.00  60.00  100
  5  \w    -96.00  -6.00   1.00   20.00    --  -27.15 -57.00 -60.00   90
  6  \w   -100.00  46.00   1.00   20.00    --  -27.15   0.00 -60.00  146
  7  \w      6.00  96.00   1.00   20.00    --   27.00  57.00-180.00   90
  8  \w      6.00  96.00   1.00   20.00    --   27.00  57.00-120.00   90
  9  \w    -99.00 -49.00   1.00   20.00    --  -27.15-160.00 150.00   50
 10  \w    -57.00  43.00   1.00   20.00    --  -27.15  77.00 -90.00  100
 11  \w    -99.00 -49.00   1.00   20.00    --  -27.15-160.00 -60.00   50
 12  \w    -42.00  -5.00   1.00   20.00    --   27.00 -57.00  30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103138861
_diffrn_orient_matrix_UB_12      0.0084841370
_diffrn_orient_matrix_UB_13      -0.0419535368
_diffrn_orient_matrix_UB_21      -0.0388147421
_diffrn_orient_matrix_UB_22      0.0980919360
_diffrn_orient_matrix_UB_23      0.0081239996
_diffrn_orient_matrix_UB_31      0.0319691932
_diffrn_orient_matrix_UB_32      0.1217383131
_diffrn_orient_matrix_UB_33      -0.0035557623
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25336
_diffrn_reflns_point_group_measured_fraction_full 1.001
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.539
_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 light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.503
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.483(3)
_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     314
_refine_ls_number_reflns         6345
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0954P)^2^+0.7770P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    1.002
_reflns_Friedel_fraction_max     1.001
_reflns_number_gt                6125
_reflns_number_total             6345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02130a2.cif
_cod_data_source_block           exp_762_abs_nofix
_cod_depositor_comments
'Adding full bibliography for 7232276--7232298.cif.'
_cod_database_code               7232276
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C16 H10 O'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.947
_reflns_odcompleteness_completeness 89.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.95
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.517(3)
 0.483(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C10(H10), C7(H7), C4(H4), C6(H6), C9(H9), C8(H8),
 C22(H22), C24(H24), C26(H26), C23(H23), C21(H21), C25(H25), C18(H18), C20(H20),
  C19(H19)
;
_shelx_res_checksum              38553
_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.798