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_7060011
_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         'C17 H8 Br2 O'
_chemical_formula_sum            'C17 H8 Br2 O'
_chemical_formula_weight         388.05
_chemical_name_systematic        5-(dibromomethylene)pyren-4(5H)-one
_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             2020-01-10
_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                 92.4372(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.88283(4)
_cell_length_b                   18.75250(17)
_cell_length_c                   17.4959(2)
_cell_measurement_reflns_used    8163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9260
_cell_measurement_theta_min      3.4500
_cell_volume                     1272.77(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_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 0.988
_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    -26.00  39.00   0.50    0.06    --   47.95 -29.00 -82.00  130
  2  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00 -90.00   88
  3  \w     35.00 131.00   0.50    0.25    --  107.75 -77.00 -90.00  192
  4  \w     94.00 178.00   0.50    0.25    --  107.75  15.00  30.00  168
  5  \w     95.00 178.00   0.50    0.25    --  107.75  29.00  78.00  166
  6  \w     95.00 178.00   0.50    0.25    --  107.75  30.00 120.00  166
  7  \w     36.00 122.00   0.50    0.06    --   47.95  29.00  78.00  172
  8  \w     35.00 106.00   0.50    0.25    --  107.75 -94.00  30.00  142
  9  \w     35.00 112.00   0.50    0.25    --  107.75-125.00 -90.00  154
 10  \w     35.00 106.00   0.50    0.25    --  107.75 -94.00-180.00  142
 11  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00-150.00   88
 12  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00 -60.00   88
 13  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00   0.00   88
 14  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00  90.00   88
 15  \w     35.00  79.00   0.50    0.25    --  107.75 -61.00 150.00   88
 16  \w     35.00 106.00   0.50    0.25    --  107.75 -94.00 150.00  142
 17  \w     35.00 106.00   0.50    0.25    --  107.75 -94.00 120.00  142
 18  \w     25.00 120.00   0.50    0.06    --   47.95  77.00-120.00  190
 19  \w     95.00 178.00   0.50    0.25    --  107.75  45.00-150.00  166
 20  \w     25.00 120.00   0.50    0.06    --   47.95  77.00 150.00  190
 21  \w    -25.00  27.00   0.50    0.06    --  -47.95  29.00  78.00  104
 22  \w    -43.00 -14.00   0.50    0.25    --  -86.25  45.00 -90.00   58
 23  \w    -43.00 -14.00   0.50    0.25    --  -86.25  45.00-150.00   58
 24  \w    -34.00  25.00   0.50    0.06    --  -47.95  37.00-150.00  118
 25  \w   -122.00 -35.00   0.50    0.06    --  -47.95 -29.00 -82.00  174
 26  \w   -120.00 -73.00   0.50    0.06    --  -47.95-125.00  30.00   94
 27  \w   -120.00 -64.00   0.50    0.06    --  -47.95 -77.00  60.00  112
 28  \w   -161.00 -74.00   0.50    0.25    --  -86.25 -29.00 -82.00  174
;
_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      0.2068081000
_diffrn_orient_matrix_UB_12      0.0310645000
_diffrn_orient_matrix_UB_13      0.0693512000
_diffrn_orient_matrix_UB_21      -0.3274410000
_diffrn_orient_matrix_UB_22      -0.0008591000
_diffrn_orient_matrix_UB_23      0.0467632000
_diffrn_orient_matrix_UB_31      0.0880137000
_diffrn_orient_matrix_UB_32      -0.0760387000
_diffrn_orient_matrix_UB_33      0.0277651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16339
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.239
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    2.025
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.8889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03897k2.cif
_cod_data_source_block           fs67
_cod_depositor_comments
'Adding full bibliography for 7060010--7060012.cif.'
_cod_database_code               7060011
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H8Br2O
_shelx_estimated_absorpt_t_max   0.691
_shelx_estimated_absorpt_t_min   0.447
_diffrn_oxdiff_digest_frames
;
01127b13eb444f30c7dc3e5dbefd6e25af0010179b9
;
_diffrn_oxdiff_digest_hkl
;
01088e8dc8b49cf33a314fe9075a889eebf5d3
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              88471
_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 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.564