Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties.
Althagafi, Ismail; Shaw, Ranjay; Tang, Cheng-Run; Panwar, Rahul; Shally, ?; Sinha, Chanda; Kumar, Amit; Zheng, Yong-Tang; Pratap, Ramendra; Organic & biomolecular chemistry 16 (2018) 7477–7487; doi:10.1039/c8ob01733f

data_7157224
_publ_section_title
;
 Chemoselective synthesis of isolated and fused fluorenones and their
 photophysical and antiviral properties.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7477
_journal_page_last               7487
_journal_paper_doi               10.1039/c8ob01733f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         '0.1(C25 H23 Br N2)'
_chemical_formula_sum            'C2.5 H2.3 Br0.1 N0.2'
_chemical_formula_weight         43.14
_chemical_name_systematic
2''-bromo-4-methyl-5'-(piperidin-1-yl)-[1,1':3',1''-terphenyl]-4'-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.900(7)
_cell_angle_gamma                90
_cell_formula_units_Z            40
_cell_length_a                   8.4375(6)
_cell_length_b                   19.2059(12)
_cell_length_c                   13.8112(10)
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.9940
_cell_measurement_theta_min      3.2640
_cell_volume                     2152.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details
;
  1 omega  -13.00   18.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0952  -99.0000    0.0000 31

  2 omega  -46.00   52.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0952   77.0000 -150.0000 98

  3 omega  -25.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -99.0000  120.0000 87

  4 omega  -22.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -99.0000  -30.0000 84

  5 omega    2.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000 -150.0000 60

  6 omega    6.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000    0.0000 83

  7 omega    1.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000  120.0000 88

  8 omega   16.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000  -90.0000 73

  9 omega  -35.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -38.0000  -30.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30605
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    1.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3311
_exptl_crystal_description       needle
_exptl_crystal_F_000             887.1716
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane and DCM'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.5261
_refine_diff_density_min         -0.7467
_refine_diff_density_rms         0.0987
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.2767
_refine_ls_goodness_of_fit_ref   1.0390
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0390
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -6
_reflns_number_gt                2795
_reflns_number_total             3776
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob01733f2.cif
_cod_data_source_block           PRS-117-3
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7157224
_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
2.a Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C19(H19a,H19b), C20(H20a,H20b), C21(H21a,H21b), C22(H22a,H22b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C10(H10), C16(H16), C18(H18), C23(H23), C25(H25),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c)
;
_olex2_submission_original_sample_id PRS-117
_olex2_submission_special_instructions 'No special instructions were received'