Synthesis and comparative studies of K-region functionalized pyrene derivatives
Shahrokhi, Farshid; Fazli Estabragh, Roxana; Zhao, Yuming; New Journal of Chemistry 44 (2020) 16786–16794; doi:10.1039/D0NJ03897K

data_7060012
_publ_section_title
;
 Synthesis and comparative studies of K-region functionalized pyrene
 derivatives
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16786
_journal_page_last               16794
_journal_paper_doi               10.1039/D0NJ03897K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30
_chemical_melting_point          '. 125.5 -126.2'
_chemical_name_systematic        'ethyl 5-hydroxypyrene-4-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.932(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9879(7)
_cell_length_b                   4.96700(10)
_cell_length_c                   18.9991(7)
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7690
_cell_measurement_theta_min      4.8400
_cell_volume                     1360.06(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.989
_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     35.00 120.00   0.50    0.40    --   47.70  44.00  11.00  170
  2  \w     94.00 178.00   0.50    2.50    --  107.75  44.00  11.00  168
  3  \w     95.00 178.00   0.50    2.50    --  107.75  30.00 -60.00  166
  4  \w     95.00 178.00   0.50    2.50    --  107.75 125.00 -90.00  166
  5  \w     95.00 178.00   0.50    2.50    --  107.75 125.00-120.00  166
  6  \w     91.00 178.00   0.50    2.50    --  107.75  61.00 -90.00  174
  7  \w     95.00 178.00   0.50    2.50    --  107.75  45.00 150.00  166
  8  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00 -90.00   88
  9  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00-150.00   88
 10  \w     35.00 106.00   0.50    2.50    --  107.75 -94.00-120.00  142
 11  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00-120.00   88
 12  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00 -60.00   88
 13  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00 -30.00   88
 14  \w     35.00 131.00   0.50    2.50    --  107.75 -77.00  30.00  192
 15  \w     35.00 112.00   0.50    2.50    --  107.75-125.00  90.00  154
 16  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00  60.00   88
 17  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00  90.00   88
 18  \w     35.00  79.00   0.50    2.50    --  107.75 -61.00  30.00   88
 19  \w     35.00 112.00   0.50    2.50    --  107.75-125.00 120.00  154
 20  \w    -24.00  56.00   0.50    0.40    --   47.70 -44.00-139.00  160
 21  \w    -16.00  28.00   0.50    0.40    --  -47.70  19.00-120.00   88
 22  \w    -42.00 -14.00   0.50    2.50    --  -86.25  44.00  11.00   56
 23  \w    -42.00  24.00   0.50    0.40    --  -47.70  44.00  11.00  132
 24  \w    -16.00  28.00   0.50    0.40    --  -47.70  19.00 150.00   88
 25  \w     25.00 120.00   0.50    0.40    --   47.70  77.00  90.00  190
 26  \w    -43.00 -14.00   0.50    2.50    --  -86.25  45.00-180.00   58
 27  \w   -120.00 -34.00   0.50    0.40    --  -47.70 -44.00-139.00  172
 28  \w   -119.00 -25.00   0.50    0.40    --  -47.70 -77.00 150.00  188
 29  \w   -119.00 -63.00   0.50    0.40    --  -47.70 -77.00 -30.00  112
 30  \w   -158.00 -73.00   0.50    2.50    --  -86.25 -44.00-139.00  170
;
_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      -0.0336278000
_diffrn_orient_matrix_UB_12      0.0732744000
_diffrn_orient_matrix_UB_13      0.0672774000
_diffrn_orient_matrix_UB_21      -0.0913289000
_diffrn_orient_matrix_UB_22      -0.1527196000
_diffrn_orient_matrix_UB_23      -0.0332833000
_diffrn_orient_matrix_UB_31      0.0441689000
_diffrn_orient_matrix_UB_32      -0.2597757000
_diffrn_orient_matrix_UB_33      0.0384956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.407
_diffrn_reflns_theta_min         3.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0641
_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^)+(0.0994P)^2^+1.0688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2471
_reflns_number_total             2855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03897k2.cif
_cod_data_source_block           fs67-2
_cod_depositor_comments
'Adding full bibliography for 7060010--7060012.cif.'
_cod_database_code               7060012
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H8Br2O
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.861
_diffrn_oxdiff_digest_frames
;
019d8280c87b9a069fafd165e4f3d2bf1c00035bd46
;
_diffrn_oxdiff_digest_hkl
;
01179635682d186d4176bd21f2c12fff3f55ee
;
_reflns_odcompleteness_completeness 99.94
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              10127
_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 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.728